# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ms198
_database_code_depnum_ccdc_archive 'CCDC 2121842'
loop_
_audit_author_name
_audit_author_address
'Marina Saab'
;Ghent University
Belgium
;
_audit_update_record             
;
2021-11-12 deposited with the CCDC.	2022-02-07 downloaded from the CCDC.
;
_audit_creation_date             2020-01-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H36 Br2 N2 Se'
_chemical_formula_sum            'C27 H36 Br2 N2 Se'
_chemical_formula_weight         627.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C27 H36 Br2 N2 Se'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   12.3667(2)
_cell_length_b                   20.3331(4)
_cell_length_c                   10.4430(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2625.93(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5307
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      73.3900
_cell_measurement_theta_min      4.3190
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.620
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42480
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       hexagonal
_exptl_crystal_F_000             1264
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 -10 -4 0.0640
-6 -2 4 0.0110
4 11 -1 0.0068
-6 -4 -4 0.0116
-2 3 -6 0.0396
-7 5 2 0.0088
6 -5 4 0.0235

_exptl_crystal_size_max          0.095
_exptl_crystal_size_mid          0.061
_exptl_crystal_size_min          0.039
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
2.5404 -10.4566 -3.5396 -0.3097 0.5681 0.7624
-6.4235 -2.4874 3.8610 -0.2091 0.3862 -0.8984
4.2088 11.1108 -0.8618 0.4622 -0.8504 0.2513
-6.3659 -3.9370 -3.5945 -0.9803 0.1286 -0.1502
-1.7561 2.9725 -6.4373 -0.7526 -0.5186 0.4057
-6.9960 4.7258 2.2712 -0.2998 -0.2049 -0.9318
5.6288 -5.2865 3.9953 0.8040 0.5531 0.2182

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12990
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.786
_diffrn_reflns_theta_min         4.349
_diffrn_ambient_temperature      100(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00 150.00  101
  2  ω     27.00  98.00   1.00    1.00    --   41.68-125.00 -30.00   71
  3  ω      6.00  83.00   1.00    1.00    --   41.68 -99.00  90.00   77
  4  ω     30.00 139.00   1.00    1.00    --  106.01 -77.00-150.00  109
  5  ω     97.00 178.00   1.00    1.00    --  106.01 125.00  90.00   81
  6  ω    103.00 178.00   1.00    1.00    --  106.01  77.00   0.00   75
  7  ω     77.00 178.00   1.00    1.00    --  106.01  61.00 -90.00  101
  8  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00-120.00  101
  9  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00  90.00  101
 10  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00   0.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0867810000
_diffrn_orient_matrix_UB_12      0.0165528000
_diffrn_orient_matrix_UB_13      0.1008896000
_diffrn_orient_matrix_UB_21      -0.0033063000
_diffrn_orient_matrix_UB_22      -0.0715312000
_diffrn_orient_matrix_UB_23      0.0484361000
_diffrn_orient_matrix_UB_31      0.0893801000
_diffrn_orient_matrix_UB_32      -0.0186923000
_diffrn_orient_matrix_UB_33      -0.0960320000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2161
_reflns_number_total             2675
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.486
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2675
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0294
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0269P)²+0.2359P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0584
_refine_ls_wR_factor_ref         0.0636
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12), C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C7(H7), C5(H5), C6(H6)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C11(H11A,H11B,H11C), C10(H10A,H10B,H10C), C14(H14A,H14B,
 H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.76482(3) 0.750000 0.30892(4) 0.01475(11) Uani 1 2 d S T P . .
Br2 Br 0.67937(3) 0.750000 0.07558(4) 0.02119(11) Uani 1 2 d S T P . .
Br1 Br 0.86264(3) 0.750000 0.51894(4) 0.02447(12) Uani 1 2 d S T P . .
N1 N 0.55927(15) 0.69643(9) 0.3964(2) 0.0114(5) Uani 1 1 d . . . . .
C2 C 0.45532(19) 0.71680(11) 0.4232(2) 0.0128(5) Uani 1 1 d . . . . .
H2 H 0.394793 0.689168 0.438743 0.015 Uiso 1 1 calc R . . . .
C3 C 0.59341(19) 0.62786(11) 0.4075(2) 0.0119(5) Uani 1 1 d . . . . .
C1 C 0.6224(3) 0.750000 0.3772(3) 0.0115(7) Uani 1 2 d S T P . .
C4 C 0.57642(19) 0.58604(11) 0.3036(3) 0.0148(6) Uani 1 1 d . . . . .
C12 C 0.5221(2) 0.60686(12) 0.1811(3) 0.0189(6) Uani 1 1 d . . . . .
H12 H 0.519405 0.656004 0.179517 0.023 Uiso 1 1 calc R . . . .
C7 C 0.66064(19) 0.54116(12) 0.5379(3) 0.0176(6) Uani 1 1 d . . . . .
H7 H 0.689079 0.525174 0.616503 0.021 Uiso 1 1 calc R . . . .
C9 C 0.6386(2) 0.65254(11) 0.6418(3) 0.0173(6) Uani 1 1 d . . . . .
H9 H 0.652167 0.698158 0.609813 0.021 Uiso 1 1 calc R . . . .
C8 C 0.63260(19) 0.60739(11) 0.5266(3) 0.0145(6) Uani 1 1 d . . . . .
C5 C 0.6062(2) 0.52019(11) 0.3215(3) 0.0188(6) Uani 1 1 d . . . . .
H5 H 0.597736 0.489904 0.253005 0.023 Uiso 1 1 calc R . . . .
C6 C 0.6474(2) 0.49856(12) 0.4357(3) 0.0211(7) Uani 1 1 d . . . . .
H6 H 0.667083 0.453650 0.444980 0.025 Uiso 1 1 calc R . . . .
C13 C 0.5836(3) 0.58392(13) 0.0627(3) 0.0325(8) Uani 1 1 d . . . . .
H13A H 0.658529 0.599412 0.067427 0.049 Uiso 1 1 calc GR . . . .
H13B H 0.549076 0.601826 -0.014191 0.049 Uiso 1 1 calc GR . . . .
H13C H 0.582751 0.535761 0.058936 0.049 Uiso 1 1 calc GR . . . .
C11 C 0.7298(2) 0.63500(13) 0.7343(3) 0.0264(7) Uani 1 1 d . . . . .
H11A H 0.714233 0.592529 0.774646 0.040 Uiso 1 1 calc GR . . . .
H11B H 0.735427 0.669038 0.800379 0.040 Uiso 1 1 calc GR . . . .
H11C H 0.798149 0.632172 0.687178 0.040 Uiso 1 1 calc GR . . . .
C10 C 0.5311(2) 0.65309(13) 0.7150(3) 0.0245(7) Uani 1 1 d . . . . .
H10A H 0.472914 0.667136 0.657415 0.037 Uiso 1 1 calc GR . . . .
H10B H 0.536091 0.683702 0.787209 0.037 Uiso 1 1 calc GR . . . .
H10C H 0.515557 0.608787 0.747007 0.037 Uiso 1 1 calc GR . . . .
C14 C 0.4049(2) 0.58105(13) 0.1780(3) 0.0284(7) Uani 1 1 d . . . . .
H14A H 0.405514 0.532856 0.177569 0.043 Uiso 1 1 calc GR . . . .
H14B H 0.368641 0.597147 0.100709 0.043 Uiso 1 1 calc GR . . . .
H14C H 0.366069 0.596741 0.253921 0.043 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 Br2 2.6561(6) . ?
Se1 Br1 2.5048(6) . ?
Se1 C1 1.900(3) . ?
N1 C2 1.379(3) . ?
N1 C3 1.461(3) . ?
N1 C1 1.355(3) . ?
C2 C2 1.350(4) 7_575 ?
C3 C4 1.395(3) . ?
C3 C8 1.398(3) . ?
C4 C12 1.506(3) . ?
C4 C5 1.402(3) . ?
C12 C13 1.524(4) . ?
C12 C14 1.541(3) . ?
C7 C8 1.396(3) . ?
C7 C6 1.384(4) . ?
C9 C8 1.515(3) . ?
C9 C11 1.526(3) . ?
C9 C10 1.534(3) . ?
C5 C6 1.369(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Br1 Se1 Br2 174.56(2) . . ?
C1 Se1 Br2 88.61(11) . . ?
C1 Se1 Br1 96.83(11) . . ?
C2 N1 C3 122.67(19) . . ?
C1 N1 C2 109.0(2) . . ?
C1 N1 C3 127.7(2) . . ?
C2 C2 N1 107.48(12) 7_575 . ?
C4 C3 N1 118.5(2) . . ?
C4 C3 C8 124.3(2) . . ?
C8 C3 N1 117.0(2) . . ?
N1 C1 Se1 126.14(14) . . ?
N1 C1 Se1 126.14(14) 7_575 . ?
N1 C1 N1 107.0(3) . 7_575 ?
C3 C4 C12 123.8(2) . . ?
C3 C4 C5 116.0(2) . . ?
C5 C4 C12 120.0(2) . . ?
C4 C12 C13 112.3(2) . . ?
C4 C12 C14 110.0(2) . . ?
C13 C12 C14 110.4(2) . . ?
C6 C7 C8 120.6(3) . . ?
C8 C9 C11 113.4(2) . . ?
C8 C9 C10 110.9(2) . . ?
C11 C9 C10 109.1(2) . . ?
C3 C8 C9 122.9(2) . . ?
C7 C8 C3 116.7(2) . . ?
C7 C8 C9 120.3(2) . . ?
C6 C5 C4 121.4(2) . . ?
C5 C6 C7 121.0(2) . . ?

_olex2_date_sample_data_collection 2019-10-01
_olex2_exptl_crystal_mounting_method 'mounted on a LithoLoop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.388
_oxdiff_exptl_absorpt_empirical_full_min 0.408
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ms199
_database_code_depnum_ccdc_archive 'CCDC 2121843'
loop_
_audit_author_name
_audit_author_address
'Marina Saab'
;Ghent University
Belgium
;
_audit_update_record             
;
2021-11-12 deposited with the CCDC.	2022-02-07 downloaded from the CCDC.
;
_audit_creation_date             2020-01-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H38 Br N2 Se, Br3'
_chemical_formula_sum            'C27 H38 Br4 N2 Se'
_chemical_formula_weight         789.15
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C27 H38 Br2 N2 Se'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.72480(10)
_cell_length_b                   18.3045(2)
_cell_length_c                   17.8287(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.1660(10)
_cell_angle_gamma                90
_cell_volume                     3141.47(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11892
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      73.7900
_cell_measurement_theta_min      3.4360
_shelx_estimated_absorpt_T_max   0.651
_shelx_estimated_absorpt_T_min   0.296
_exptl_absorpt_coefficient_mu    7.703
_exptl_absorpt_correction_T_max  0.846
_exptl_absorpt_correction_T_min  0.513
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1552
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 -5 -9 0.0257
-5 4 8 0.0070
6 0 0 0.0345
-3 -1 -10 0.0269
-3 8 8 0.0323
5 -6 3 0.0230

_exptl_crystal_size_max          0.209
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.061
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2.3266 -5.0857 -8.8485 0.1053 0.4431 0.8903
-4.8285 3.8384 7.6426 0.1637 0.6812 -0.7136
6.2535 0.4380 -0.1244 -0.2326 -0.9718 -0.0384
-2.5916 -0.7218 -9.7471 -0.2371 0.5695 0.7871
-2.5309 7.5149 8.2530 -0.1517 0.3678 -0.9174
4.9236 -5.6152 3.4127 0.3826 -0.9218 -0.0622

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            30317
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.924
_diffrn_reflns_theta_min         3.479
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -17.00   1.00    1.00    --  -41.68 -38.00  60.00   99
  2  ω    -66.00  33.00   1.00    1.00    --  -41.68  38.00-120.00   99
  3  ω    -38.00  83.00   1.00    1.00    --   41.68 -19.00 -90.00  121
  4  ω    103.00 178.00   1.00    1.00    --  106.01  77.00 150.00   75
  5  ω     33.00 112.00   1.00    1.00    --  106.01-125.00  90.00   79
  6  ω     34.00 135.00   1.00    1.00    --  106.01 -61.00  90.00  101
  7  ω    103.00 178.00   1.00    1.00    --  106.01  77.00   0.00   75
  8  ω    103.00 178.00   1.00    1.00    --  106.01  77.00 120.00   75
  9  ω    103.00 178.00   1.00    1.00    --  106.01  77.00-150.00   75
 10  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00 -30.00  101
 11  ω     17.00 116.00   1.00    1.00    --   41.68  38.00 -60.00   99
 12  ω    103.00 178.00   1.00    1.00    --  106.01  77.00  60.00   75
 13  ω     78.00 178.00   1.00    1.00    --  106.01  30.00  30.00  100
 14  ω     53.00 178.00   1.00    1.00    --  106.01  15.00-180.00  125
 15  ω     80.00 178.00   1.00    1.00    --  106.01  45.00 -60.00   98
 16  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00-180.00  101
 17  ω     27.00  98.00   1.00    1.00    --   41.68-125.00  60.00   71
 18  ω     33.00  58.00   1.00    1.00    --  106.01-125.00 -60.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0313593000
_diffrn_orient_matrix_UB_12      -0.0725198000
_diffrn_orient_matrix_UB_13      0.0380310000
_diffrn_orient_matrix_UB_21      -0.1568617000
_diffrn_orient_matrix_UB_22      0.0157540000
_diffrn_orient_matrix_UB_23      -0.0178829000
_diffrn_orient_matrix_UB_31      -0.0048831000
_diffrn_orient_matrix_UB_32      -0.0396995000
_diffrn_orient_matrix_UB_33      -0.0765132000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5083
_reflns_number_total             6259
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         6259
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0290
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0238P)²+0.7421P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0567
_refine_ls_wR_factor_ref         0.0617
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C13(H13), C22(H22), C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C18(H18), C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12C,H12A,H12B), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C27(H27A,
 H27B,H27C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.22974(3) 0.69128(2) 0.53257(2) 0.02632(9) Uani 1 1 d . . . . .
Br2 Br 0.39801(3) 0.64372(2) 0.34107(2) 0.02394(8) Uani 1 1 d . . . . .
Br3 Br 0.27089(3) 0.54059(2) 0.26003(2) 0.02209(8) Uani 1 1 d . . . . .
Br4 Br 0.15583(4) 0.43756(2) 0.18216(2) 0.03369(10) Uani 1 1 d . . . . .
Se1 Se 0.46149(3) 0.69264(2) 0.51791(2) 0.02013(8) Uani 1 1 d . . . . .
N1 N 0.6948(2) 0.72447(12) 0.61574(14) 0.0163(5) Uani 1 1 d . . . . .
N2 N 0.5246(2) 0.72210(12) 0.68420(14) 0.0158(5) Uani 1 1 d . . . . .
C1 C 0.5597(3) 0.71560(14) 0.61625(17) 0.0149(6) Uani 1 1 d . . . . .
C2 C 0.7681(3) 0.73552(16) 0.69298(17) 0.0188(6) Uani 1 1 d . . . . .
H2A H 0.823996 0.780903 0.696442 0.023 Uiso 1 1 calc R . . . .
H2B H 0.829453 0.693656 0.709444 0.023 Uiso 1 1 calc R . . . .
C3 C 0.6486(3) 0.74116(17) 0.74005(18) 0.0195(7) Uani 1 1 d . . . . .
H3A H 0.660879 0.706239 0.782877 0.023 Uiso 1 1 calc R . . . .
H3B H 0.640904 0.791239 0.760010 0.023 Uiso 1 1 calc R . . . .
C4 C 0.7616(3) 0.72149(15) 0.54905(17) 0.0166(6) Uani 1 1 d . . . . .
C5 C 0.7788(3) 0.78708(16) 0.51075(18) 0.0194(6) Uani 1 1 d . . . . .
C6 C 0.8433(3) 0.78300(17) 0.44626(19) 0.0241(7) Uani 1 1 d . . . . .
H6 H 0.855798 0.826286 0.418626 0.029 Uiso 1 1 calc R . . . .
C7 C 0.8897(3) 0.71684(17) 0.42141(19) 0.0263(7) Uani 1 1 d . . . . .
H7 H 0.933377 0.715263 0.377026 0.032 Uiso 1 1 calc R . . . .
C8 C 0.8730(3) 0.65353(17) 0.46062(19) 0.0239(7) Uani 1 1 d . . . . .
H8 H 0.905719 0.608708 0.442895 0.029 Uiso 1 1 calc R . . . .
C9 C 0.8091(3) 0.65374(16) 0.52589(17) 0.0183(6) Uani 1 1 d . . . . .
C10 C 0.7986(3) 0.58379(15) 0.57051(18) 0.0197(7) Uani 1 1 d . . . . .
H10 H 0.745211 0.594948 0.613107 0.024 Uiso 1 1 calc R . . . .
C11 C 0.9437(3) 0.55784(17) 0.6050(2) 0.0285(8) Uani 1 1 d . . . . .
H11A H 0.998492 0.546847 0.564291 0.043 Uiso 1 1 calc GR . . . .
H11B H 0.935472 0.513746 0.635200 0.043 Uiso 1 1 calc GR . . . .
H11C H 0.989937 0.596328 0.637487 0.043 Uiso 1 1 calc GR . . . .
C12 C 0.7207(3) 0.52395(17) 0.5220(2) 0.0286(8) Uani 1 1 d . . . . .
H12C H 0.775106 0.508922 0.482448 0.043 Uiso 1 1 calc GR . . . .
H12A H 0.630341 0.542696 0.498534 0.043 Uiso 1 1 calc GR . . . .
H12B H 0.706578 0.481860 0.554056 0.043 Uiso 1 1 calc GR . . . .
C13 C 0.7305(3) 0.86052(16) 0.53729(19) 0.0240(7) Uani 1 1 d . . . . .
H13 H 0.689774 0.852117 0.584990 0.029 Uiso 1 1 calc R . . . .
C14 C 0.8521(4) 0.91303(19) 0.5555(2) 0.0419(10) Uani 1 1 d . . . . .
H14A H 0.923962 0.890331 0.592236 0.063 Uiso 1 1 calc GR . . . .
H14B H 0.819854 0.958130 0.576949 0.063 Uiso 1 1 calc GR . . . .
H14C H 0.890701 0.924424 0.508978 0.063 Uiso 1 1 calc GR . . . .
C15 C 0.6176(4) 0.89396(19) 0.4791(2) 0.0406(10) Uani 1 1 d . . . . .
H15A H 0.655546 0.903875 0.432048 0.061 Uiso 1 1 calc GR . . . .
H15B H 0.585041 0.939707 0.499074 0.061 Uiso 1 1 calc GR . . . .
H15C H 0.539671 0.859742 0.468785 0.061 Uiso 1 1 calc GR . . . .
C16 C 0.3886(3) 0.72247(15) 0.70745(18) 0.0161(6) Uani 1 1 d . . . . .
C17 C 0.3163(3) 0.78883(15) 0.70506(18) 0.0193(7) Uani 1 1 d . . . . .
C18 C 0.1876(3) 0.78796(16) 0.73072(19) 0.0221(7) Uani 1 1 d . . . . .
H18 H 0.134515 0.831630 0.729423 0.026 Uiso 1 1 calc R . . . .
C19 C 0.1361(3) 0.72457(16) 0.75798(18) 0.0220(7) Uani 1 1 d . . . . .
H19 H 0.048894 0.725384 0.776139 0.026 Uiso 1 1 calc R . . . .
C20 C 0.2100(3) 0.65964(16) 0.75925(18) 0.0195(7) Uani 1 1 d . . . . .
H20 H 0.171499 0.616236 0.776789 0.023 Uiso 1 1 calc R . . . .
C21 C 0.3397(3) 0.65738(15) 0.73518(17) 0.0166(6) Uani 1 1 d . . . . .
C22 C 0.4222(3) 0.58656(15) 0.73750(18) 0.0192(7) Uani 1 1 d . . . . .
H22 H 0.519997 0.599296 0.731443 0.023 Uiso 1 1 calc R . . . .
C23 C 0.3640(3) 0.53791(16) 0.67080(19) 0.0257(7) Uani 1 1 d . . . . .
H23A H 0.265209 0.528671 0.672453 0.039 Uiso 1 1 calc GR . . . .
H23B H 0.414463 0.491412 0.674032 0.039 Uiso 1 1 calc GR . . . .
H23C H 0.375014 0.562438 0.623164 0.039 Uiso 1 1 calc GR . . . .
C24 C 0.4256(3) 0.54670(16) 0.81308(19) 0.0257(7) Uani 1 1 d . . . . .
H24A H 0.472819 0.577241 0.854009 0.038 Uiso 1 1 calc GR . . . .
H24B H 0.475855 0.500451 0.811363 0.038 Uiso 1 1 calc GR . . . .
H24C H 0.330420 0.536847 0.822338 0.038 Uiso 1 1 calc GR . . . .
C25 C 0.3739(3) 0.85970(15) 0.6779(2) 0.0245(7) Uani 1 1 d . . . . .
H25 H 0.468010 0.849153 0.663993 0.029 Uiso 1 1 calc R . . . .
C26 C 0.3916(3) 0.91540(17) 0.7423(2) 0.0331(9) Uani 1 1 d . . . . .
H26A H 0.301574 0.924327 0.759292 0.050 Uiso 1 1 calc GR . . . .
H26B H 0.427507 0.961255 0.724367 0.050 Uiso 1 1 calc GR . . . .
H26C H 0.457152 0.896369 0.784656 0.050 Uiso 1 1 calc GR . . . .
C27 C 0.2840(4) 0.89013(18) 0.6078(2) 0.0358(9) Uani 1 1 d . . . . .
H27A H 0.277163 0.853984 0.566905 0.054 Uiso 1 1 calc GR . . . .
H27B H 0.325997 0.935040 0.591582 0.054 Uiso 1 1 calc GR . . . .
H27C H 0.190881 0.900908 0.619935 0.054 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Se1 2.3056(4) . ?
Br2 Br3 2.5830(5) . ?
Br3 Br4 2.5090(5) . ?
Se1 C1 1.920(3) . ?
N1 C1 1.325(3) . ?
N1 C2 1.472(4) . ?
N1 C4 1.435(4) . ?
N2 C1 1.310(4) . ?
N2 C3 1.492(4) . ?
N2 C16 1.441(3) . ?
C2 C3 1.530(4) . ?
C4 C5 1.403(4) . ?
C4 C9 1.406(4) . ?
C5 C6 1.388(4) . ?
C5 C13 1.521(4) . ?
C6 C7 1.387(4) . ?
C7 C8 1.375(4) . ?
C8 C9 1.395(4) . ?
C9 C10 1.519(4) . ?
C10 C11 1.532(4) . ?
C10 C12 1.528(4) . ?
C13 C14 1.522(4) . ?
C13 C15 1.528(4) . ?
C16 C17 1.401(4) . ?
C16 C21 1.399(4) . ?
C17 C18 1.392(4) . ?
C17 C25 1.520(4) . ?
C18 C19 1.379(4) . ?
C19 C20 1.387(4) . ?
C20 C21 1.389(4) . ?
C21 C22 1.522(4) . ?
C22 C23 1.528(4) . ?
C22 C24 1.529(4) . ?
C25 C26 1.527(4) . ?
C25 C27 1.525(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Br4 Br3 Br2 177.796(18) . . ?
C1 Se1 Br1 105.43(8) . . ?
C1 N1 C2 111.1(2) . . ?
C1 N1 C4 124.6(3) . . ?
C4 N1 C2 124.4(2) . . ?
C1 N2 C3 110.3(2) . . ?
C1 N2 C16 129.5(3) . . ?
C16 N2 C3 119.6(2) . . ?
N1 C1 Se1 112.7(2) . . ?
N2 C1 Se1 134.7(2) . . ?
N2 C1 N1 112.6(3) . . ?
N1 C2 C3 102.6(2) . . ?
N2 C3 C2 102.9(2) . . ?
C5 C4 N1 118.0(2) . . ?
C5 C4 C9 123.0(3) . . ?
C9 C4 N1 118.9(3) . . ?
C4 C5 C13 122.8(3) . . ?
C6 C5 C4 117.1(3) . . ?
C6 C5 C13 120.1(3) . . ?
C7 C6 C5 121.2(3) . . ?
C8 C7 C6 120.4(3) . . ?
C7 C8 C9 121.4(3) . . ?
C4 C9 C10 122.7(3) . . ?
C8 C9 C4 116.8(3) . . ?
C8 C9 C10 120.4(3) . . ?
C9 C10 C11 110.2(2) . . ?
C9 C10 C12 111.9(3) . . ?
C12 C10 C11 111.0(3) . . ?
C5 C13 C14 111.1(3) . . ?
C5 C13 C15 111.5(3) . . ?
C14 C13 C15 110.7(3) . . ?
C17 C16 N2 118.2(2) . . ?
C21 C16 N2 118.0(2) . . ?
C21 C16 C17 123.7(3) . . ?
C16 C17 C25 122.9(3) . . ?
C18 C17 C16 116.8(3) . . ?
C18 C17 C25 120.3(3) . . ?
C19 C18 C17 120.9(3) . . ?
C18 C19 C20 120.9(3) . . ?
C19 C20 C21 120.7(3) . . ?
C16 C21 C22 122.0(2) . . ?
C20 C21 C16 117.0(3) . . ?
C20 C21 C22 121.0(3) . . ?
C21 C22 C23 109.8(3) . . ?
C21 C22 C24 112.1(2) . . ?
C24 C22 C23 111.5(2) . . ?
C17 C25 C26 109.7(3) . . ?
C17 C25 C27 112.2(3) . . ?
C27 C25 C26 111.3(3) . . ?

_olex2_date_sample_data_collection 2019-10-23
_olex2_exptl_crystal_mounting_method 'mounted on a LithoLoop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.407
_oxdiff_exptl_absorpt_empirical_full_min 0.694
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ms228
_database_code_depnum_ccdc_archive 'CCDC 2121847'
loop_
_audit_author_name
_audit_author_address
'Marina Saab'
;Ghent University
Belgium
;
_audit_update_record             
;
2021-11-12 deposited with the CCDC.	2022-02-07 downloaded from the CCDC.
;
_audit_creation_date             2020-01-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H34 Br Cl2 N2 Se, Br3'
_chemical_formula_sum            'C27 H34 Br4 Cl2 N2 Se'
_chemical_formula_weight         856.02
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C27 H34 Br2 Cl2 N2 Se'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   9.8098(2)
_cell_length_b                   17.0515(2)
_cell_length_c                   10.0380(2)
_cell_angle_alpha                90
_cell_angle_beta                 110.109(2)
_cell_angle_gamma                90
_cell_volume                     1576.72(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9049
_cell_measurement_temperature    100.49(10)
_cell_measurement_theta_max      73.6960
_cell_measurement_theta_min      4.6590
_shelx_estimated_absorpt_T_max   0.555
_shelx_estimated_absorpt_T_min   0.282
_exptl_absorpt_coefficient_mu    9.257
_exptl_absorpt_correction_T_max  0.855
_exptl_absorpt_correction_T_min  0.389
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.803
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             836
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-6 1 4 0.0817
0 5 -6 0.0594
6 -2 -3 0.0384
-1 -5 6 0.0706
-5 3 5 0.0721
4 8 0 0.0286
5 -3 -5 0.0171
-4 -8 0 0.0433

_exptl_crystal_size_max          0.183
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.072
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-6.0746 1.3715 3.8137 0.0433 0.1847 0.9818
0.3905 5.1590 -5.5377 0.2114 0.8815 -0.4221
6.1757 -2.2940 -2.9697 -0.0808 -0.3409 -0.9366
-1.0637 -4.8317 5.7834 -0.1995 -0.8312 0.5189
-5.0055 3.1409 5.1233 0.2965 -0.0698 0.9525
3.7781 8.4685 0.1964 0.8872 -0.2129 -0.4094
5.0336 -3.0634 -5.1163 -0.2884 0.0679 -0.9551
-3.8576 -8.3958 -0.1066 -0.8801 0.2112 0.4251

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15522
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.909
_diffrn_reflns_theta_min         4.691
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.49(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -17.00   1.00    1.00    --  -41.68 -38.00-120.00   99
  2  ω     27.00  98.00   1.00    1.00    --   41.68-125.00-150.00   71
  3  ω    -30.00  70.00   1.00    1.00    --   41.68 -57.00 150.00  100
  4  ω    103.00 178.00   1.00    1.00    --  106.01  77.00-120.00   75
  5  ω     77.00 178.00   1.00    1.00    --  106.01  61.00  60.00  101
  6  ω     23.00 107.00   1.00    1.00    --  106.01 -94.00-120.00   84
  7  ω     33.00 112.00   1.00    1.00    --  106.01-125.00-180.00   79
  8  ω    103.00 178.00   1.00    1.00    --  106.01  77.00 150.00   75
  9  ω     33.00 112.00   1.00    1.00    --  106.01-125.00-120.00   79
 10  ω    103.00 178.00   1.00    1.00    --  106.01  77.00  30.00   75
 11  ω    -87.00  -6.00   1.00    1.00    --  -41.68 125.00 -60.00   81
 12  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00  30.00  101
 13  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00 150.00  101
 14  ω     77.00 178.00   1.00    1.00    --  106.01  61.00 120.00  101
 15  ω     77.00 178.00   1.00    1.00    --  106.01  61.00-150.00  101
 16  ω     30.00 139.00   1.00    1.00    --  106.01 -77.00 -60.00  109
 17  ω     77.00 106.00   1.00    1.00    --  106.01  61.00 -90.00   29
 18  ω     80.00 178.00   1.00    1.00    --  106.01  45.00 -30.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0402249000
_diffrn_orient_matrix_UB_12      0.0857844000
_diffrn_orient_matrix_UB_13      0.0445791000
_diffrn_orient_matrix_UB_21      -0.1123942000
_diffrn_orient_matrix_UB_22      0.0282726000
_diffrn_orient_matrix_UB_23      -0.1407748000
_diffrn_orient_matrix_UB_31      -0.1171091000
_diffrn_orient_matrix_UB_32      0.0022817000
_diffrn_orient_matrix_UB_33      0.0700958000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3017
_reflns_number_total             3261
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         2.249
_refine_diff_density_min         -0.700
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         3261
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0320
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0296P)²+3.8954P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0747
_refine_ls_wR_factor_ref         0.0764
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C14(H14A,H14B,
 H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.34384(5) 0.250000 0.35324(5) 0.02004(11) Uani 1 2 d S T P . .
Se1 Se 0.54829(5) 0.250000 0.56209(5) 0.01663(11) Uani 1 2 d S T P . .
Cl1 Cl 1.02936(8) 0.35336(4) 0.44276(9) 0.02442(17) Uani 1 1 d . . . . .
N1 N 0.7780(2) 0.31393(13) 0.4769(2) 0.0138(5) Uani 1 1 d . . . . .
C1 C 0.7028(4) 0.250000 0.4917(4) 0.0146(8) Uani 1 2 d S T P . .
C2 C 0.9039(3) 0.29007(16) 0.4567(3) 0.0162(6) Uani 1 1 d . . . . .
C3 C 0.7326(3) 0.39544(15) 0.4742(3) 0.0134(5) Uani 1 1 d . . . . .
C4 C 0.6396(3) 0.42538(16) 0.3447(3) 0.0154(5) Uani 1 1 d . . . . .
C5 C 0.6038(3) 0.50442(17) 0.3445(3) 0.0201(6) Uani 1 1 d . . . . .
H5 H 0.542487 0.527843 0.258989 0.024 Uiso 1 1 calc R . . . .
C6 C 0.6556(3) 0.54954(17) 0.4661(3) 0.0211(6) Uani 1 1 d . . . . .
H6 H 0.628740 0.603217 0.463053 0.025 Uiso 1 1 calc R . . . .
C7 C 0.7452(3) 0.51768(17) 0.5910(3) 0.0189(6) Uani 1 1 d . . . . .
H7 H 0.778024 0.549421 0.673733 0.023 Uiso 1 1 calc R . . . .
C8 C 0.7891(3) 0.43932(16) 0.5986(3) 0.0159(6) Uani 1 1 d . . . . .
C9 C 0.8900(3) 0.40559(18) 0.7376(3) 0.0227(6) Uani 1 1 d . . . . .
H9 H 0.915638 0.350802 0.719656 0.027 Uiso 1 1 calc R . . . .
C10 C 1.0306(4) 0.4532(2) 0.7949(4) 0.0334(8) Uani 1 1 d . . . . .
H10A H 1.077287 0.455508 0.722969 0.050 Uiso 1 1 calc GR . . . .
H10B H 1.096344 0.427979 0.880781 0.050 Uiso 1 1 calc GR . . . .
H10C H 1.008249 0.506440 0.817748 0.050 Uiso 1 1 calc GR . . . .
C11 C 0.8123(4) 0.4023(3) 0.8461(4) 0.0375(9) Uani 1 1 d . . . . .
H11A H 0.788281 0.455694 0.866966 0.056 Uiso 1 1 calc GR . . . .
H11B H 0.875909 0.377666 0.933582 0.056 Uiso 1 1 calc GR . . . .
H11C H 0.722904 0.371610 0.807368 0.056 Uiso 1 1 calc GR . . . .
C12 C 0.5835(3) 0.37648(17) 0.2105(3) 0.0200(6) Uani 1 1 d . . . . .
H12 H 0.574906 0.321111 0.239430 0.024 Uiso 1 1 calc R . . . .
C13 C 0.6898(4) 0.3769(2) 0.1281(4) 0.0303(7) Uani 1 1 d . . . . .
H13A H 0.703088 0.430806 0.100966 0.045 Uiso 1 1 calc GR . . . .
H13B H 0.650639 0.344596 0.042669 0.045 Uiso 1 1 calc GR . . . .
H13C H 0.783564 0.355576 0.188272 0.045 Uiso 1 1 calc GR . . . .
C14 C 0.4334(4) 0.4023(2) 0.1115(4) 0.0292(7) Uani 1 1 d . . . . .
H14A H 0.365841 0.403324 0.164258 0.044 Uiso 1 1 calc GR . . . .
H14B H 0.398112 0.365260 0.032415 0.044 Uiso 1 1 calc GR . . . .
H14C H 0.440088 0.454815 0.074643 0.044 Uiso 1 1 calc GR . . . .
Br2 Br 0.05572(6) 0.250000 0.10703(7) 0.04672(17) Uani 1 2 d S T P . .
Br3 Br 0.17697(5) 0.250000 -0.08301(5) 0.02775(13) Uani 1 2 d S T P . .
Br4 Br 0.31667(9) 0.250000 -0.25016(7) 0.0555(2) Uani 1 2 d S T P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Se1 2.3508(6) . ?
Se1 C1 1.880(4) . ?
Cl1 C2 1.678(3) . ?
N1 C1 1.353(3) . ?
N1 C2 1.380(4) . ?
N1 C3 1.457(3) . ?
C2 C2 1.367(6) 4_565 ?
C3 C4 1.403(4) . ?
C3 C8 1.396(4) . ?
C4 C5 1.393(4) . ?
C4 C12 1.518(4) . ?
C5 C6 1.383(4) . ?
C6 C7 1.372(4) . ?
C7 C8 1.398(4) . ?
C8 C9 1.519(4) . ?
C9 C10 1.532(4) . ?
C9 C11 1.530(5) . ?
C12 C13 1.537(4) . ?
C12 C14 1.531(4) . ?
Br2 Br3 2.5719(8) . ?
Br3 Br4 2.5048(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Se1 Br1 102.47(13) . . ?
C1 N1 C2 109.1(2) . . ?
C1 N1 C3 126.6(2) . . ?
C2 N1 C3 124.2(2) . . ?
N1 C1 Se1 125.59(17) . . ?
N1 C1 Se1 125.60(17) 4_565 . ?
N1 C1 N1 107.4(3) 4_565 . ?
N1 C2 Cl1 122.8(2) . . ?
C2 C2 Cl1 130.02(10) 4_565 . ?
C2 C2 N1 107.15(15) 4_565 . ?
C4 C3 N1 117.5(2) . . ?
C8 C3 N1 118.0(2) . . ?
C8 C3 C4 124.4(3) . . ?
C3 C4 C12 123.0(3) . . ?
C5 C4 C3 115.9(3) . . ?
C5 C4 C12 121.1(3) . . ?
C6 C5 C4 121.4(3) . . ?
C7 C6 C5 120.8(3) . . ?
C6 C7 C8 121.1(3) . . ?
C3 C8 C7 116.3(3) . . ?
C3 C8 C9 123.5(3) . . ?
C7 C8 C9 120.2(3) . . ?
C8 C9 C10 111.2(3) . . ?
C8 C9 C11 110.0(3) . . ?
C11 C9 C10 110.9(3) . . ?
C4 C12 C13 111.6(3) . . ?
C4 C12 C14 113.1(3) . . ?
C14 C12 C13 109.2(3) . . ?
Br4 Br3 Br2 174.83(3) . . ?

_olex2_date_sample_data_collection 2019-11-28
_olex2_exptl_crystal_mounting_method 'mounted on a LithoLoop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.557
_oxdiff_exptl_absorpt_empirical_full_min 0.693
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ms351-8
_database_code_depnum_ccdc_archive 'CCDC 2121852'
loop_
_audit_author_name
_audit_author_address
'Marina Saab'
;Ghent University
Belgium
;
_audit_update_record             
;
2021-11-12 deposited with the CCDC.	2022-02-07 downloaded from the CCDC.
;
_audit_creation_date             2021-10-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H24 Br N2 S, Br'
_chemical_formula_sum            'C15 H24 Br2 N2 S'
_chemical_formula_weight         424.22
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H24 N2 S Br2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.4976(9)
_cell_length_b                   7.4915(5)
_cell_length_c                   22.3272(17)
_cell_angle_alpha                90
_cell_angle_beta                 101.384(8)
_cell_angle_gamma                90
_cell_volume                     1721.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4025
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      73.5240
_cell_measurement_theta_min      3.9690
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.037
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.655
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             856
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 -1 -14 0.0693
-3 -4 -5 0.0852
-4 -2 12 0.0674
-1 2 13 0.0441
6 -2 -7 0.0325
-5 2 9 0.0338
6 0 5 0.0460
1 5 -3 0.0891
-6 0 -4 0.0509

_exptl_crystal_size_max          0.221
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.079
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
2.4881 -0.5469 -14.1840 0.0288 0.1240 0.9919
-3.0559 -3.8492 -4.6012 0.2288 0.9560 0.1835
-4.2633 -1.6315 11.7922 0.1007 0.4173 -0.9032
-0.5963 2.1040 13.0100 -0.1222 -0.5134 -0.8494
5.6651 -2.2407 -6.7837 0.7409 -0.1768 0.6479
-5.4217 1.8889 8.8767 -0.6204 0.1478 -0.7703
5.8612 -0.0402 4.7817 0.6477 -0.7576 -0.0804
1.3394 4.7087 -2.7125 -0.6721 -0.7094 0.2121
-5.9462 0.0422 -4.4372 -0.6489 0.7588 0.0554

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0910
_diffrn_reflns_av_unetI/netI     0.0743
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            13193
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.261
_diffrn_reflns_theta_min         4.039
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -17.00   1.00    1.00    --  -41.68 -38.00 150.00   99
  2  ω    -87.00  -6.00   1.00    1.00    --  -41.68 125.00 -60.00   81
  3  ω      6.00  83.00   1.00    1.00    --   41.68 -99.00-180.00   77
  4  ω     78.00 178.00   1.00    2.00    --  106.01  30.00  90.00  100
  5  ω     23.00 107.00   1.00    2.00    --  106.01 -94.00-150.00   84
  6  ω     97.00 178.00   1.00    2.00    --  106.01 125.00 -90.00   81
  7  ω     33.00 132.00   1.00    2.00    --  106.01 -45.00 -90.00   99
  8  ω    103.00 178.00   1.00    2.00    --  106.01  77.00-180.00   75
  9  ω     23.00 107.00   1.00    2.00    --  106.01 -94.00 -90.00   84
 10  ω     28.00 108.00   1.00    2.00    --  106.01-106.00 147.58   80
 11  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00 -60.00  101
 12  ω   -116.00 -17.00   1.00    1.00    --  -41.68 -38.00  30.00   99
 13  ω      8.00  42.00   1.00    1.00    --   41.68  82.00 103.00   34
 14  ω     80.00 178.00   1.00    2.00    --  106.01  48.00  12.10   98
 15  ω     53.00 178.00   1.00    2.00    --  106.01  15.00 -30.00  125
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0928493000
_diffrn_orient_matrix_UB_12      -0.1574429000
_diffrn_orient_matrix_UB_13      0.0203245000
_diffrn_orient_matrix_UB_21      -0.1112758000
_diffrn_orient_matrix_UB_22      -0.1323505000
_diffrn_orient_matrix_UB_23      -0.0231560000
_diffrn_orient_matrix_UB_31      0.0378352000
_diffrn_orient_matrix_UB_32      -0.0021405000
_diffrn_orient_matrix_UB_33      -0.0632092000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2584
_reflns_number_total             3409
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         1.483
_refine_diff_density_min         -0.765
_refine_diff_density_rms         0.169
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3409
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0609
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0992P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1548
_refine_ls_wR_factor_ref         0.1775
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C11(H11A,
 H11B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.58506(7) 0.58172(9) 0.77296(3) 0.0409(2) Uani 1 1 d . . . . .
S1 S 0.65369(14) 0.66475(17) 0.68293(7) 0.0314(3) Uani 1 1 d . . . . .
N1 N 0.6510(5) 0.3262(6) 0.6359(2) 0.0279(9) Uani 1 1 d . . . . .
N2 N 0.4649(5) 0.4619(6) 0.6113(2) 0.0291(10) Uani 1 1 d . . . . .
C1 C 0.5871(5) 0.4776(7) 0.6426(3) 0.0277(11) Uani 1 1 d . . . . .
C2 C 0.5672(6) 0.2134(8) 0.5978(3) 0.0311(12) Uani 1 1 d . . . . .
H2 H 0.586608 0.097254 0.585129 0.037 Uiso 1 1 calc R . . . .
C3 C 0.4521(6) 0.3002(8) 0.5822(3) 0.0326(12) Uani 1 1 d . . . . .
H3 H 0.376222 0.256600 0.555770 0.039 Uiso 1 1 calc R . . . .
C4 C 0.3612(6) 0.5994(7) 0.6084(3) 0.0296(11) Uani 1 1 d . . . . .
H4 H 0.384415 0.676515 0.645509 0.036 Uiso 1 1 calc R . . . .
C5 C 0.2325(6) 0.5104(8) 0.6101(3) 0.0362(13) Uani 1 1 d . . . . .
H5A H 0.240452 0.437602 0.647654 0.043 Uiso 1 1 calc R . . . .
H5B H 0.208091 0.430231 0.574421 0.043 Uiso 1 1 calc R . . . .
C6 C 0.1270(6) 0.6531(8) 0.6089(3) 0.0386(14) Uani 1 1 d . . . . .
H6A H 0.042225 0.594150 0.608035 0.046 Uiso 1 1 calc R . . . .
H6B H 0.147726 0.725827 0.646643 0.046 Uiso 1 1 calc R . . . .
C7 C 0.1169(7) 0.7744(8) 0.5535(3) 0.0380(14) Uani 1 1 d . . . . .
H7A H 0.087483 0.703930 0.515778 0.046 Uiso 1 1 calc R . . . .
H7B H 0.051572 0.868700 0.555115 0.046 Uiso 1 1 calc R . . . .
C8 C 0.2468(6) 0.8597(8) 0.5517(3) 0.0356(13) Uani 1 1 d . . . . .
H8A H 0.271827 0.939384 0.587432 0.043 Uiso 1 1 calc R . . . .
H8B H 0.238637 0.933528 0.514310 0.043 Uiso 1 1 calc R . . . .
C9 C 0.3535(6) 0.7191(8) 0.5521(3) 0.0357(13) Uani 1 1 d . . . . .
H9A H 0.333342 0.645978 0.514522 0.043 Uiso 1 1 calc R . . . .
H9B H 0.438143 0.778735 0.553374 0.043 Uiso 1 1 calc R . . . .
C10 C 0.7874(6) 0.2857(7) 0.6625(3) 0.0301(11) Uani 1 1 d . . . . .
H10 H 0.827989 0.394874 0.684038 0.036 Uiso 1 1 calc R . . . .
C11 C 0.8612(6) 0.2383(7) 0.6120(3) 0.0310(12) Uani 1 1 d . . . . .
H11A H 0.859863 0.341465 0.584220 0.037 Uiso 1 1 calc R . . . .
H11B H 0.817786 0.136703 0.587886 0.037 Uiso 1 1 calc R . . . .
C12 C 1.0021(6) 0.1884(8) 0.6395(3) 0.0331(12) Uani 1 1 d . . . . .
H12A H 1.046864 0.151480 0.606440 0.040 Uiso 1 1 calc R . . . .
H12B H 1.047863 0.293999 0.660031 0.040 Uiso 1 1 calc R . . . .
C13 C 1.0080(6) 0.0370(8) 0.6855(3) 0.0363(13) Uani 1 1 d . . . . .
H13A H 1.099841 0.011213 0.703897 0.044 Uiso 1 1 calc R . . . .
H13B H 0.969662 -0.072080 0.664126 0.044 Uiso 1 1 calc R . . . .
C14 C 0.9345(6) 0.0849(8) 0.7358(3) 0.0342(13) Uani 1 1 d . . . . .
H14A H 0.978599 0.186125 0.759861 0.041 Uiso 1 1 calc R . . . .
H14B H 0.936166 -0.018229 0.763641 0.041 Uiso 1 1 calc R . . . .
C15 C 0.7934(6) 0.1358(7) 0.7096(3) 0.0312(12) Uani 1 1 d . . . . .
H15A H 0.750862 0.175584 0.743144 0.037 Uiso 1 1 calc R . . . .
H15B H 0.745943 0.030133 0.690088 0.037 Uiso 1 1 calc R . . . .
Br2 Br 0.73393(6) 0.74385(8) 0.57760(3) 0.0347(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 S1 2.3490(16) . ?
S1 C1 1.737(6) . ?
N1 C1 1.341(7) . ?
N1 C2 1.384(7) . ?
N1 C10 1.470(8) . ?
N2 C1 1.339(8) . ?
N2 C3 1.369(8) . ?
N2 C4 1.491(7) . ?
C2 H2 0.9500 . ?
C2 C3 1.356(9) . ?
C3 H3 0.9500 . ?
C4 H4 1.0000 . ?
C4 C5 1.514(8) . ?
C4 C9 1.532(8) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.536(8) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.522(9) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.514(9) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.537(8) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10 1.0000 . ?
C10 C11 1.530(8) . ?
C10 C15 1.531(8) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.532(9) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.522(9) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.526(9) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.529(8) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 Br1 94.02(18) . . ?
C1 N1 C2 108.3(5) . . ?
C1 N1 C10 126.8(5) . . ?
C2 N1 C10 125.0(5) . . ?
C1 N2 C3 108.6(5) . . ?
C1 N2 C4 125.3(5) . . ?
C3 N2 C4 126.0(5) . . ?
N1 C1 S1 125.5(4) . . ?
N2 C1 S1 126.0(4) . . ?
N2 C1 N1 108.5(5) . . ?
N1 C2 H2 126.5 . . ?
C3 C2 N1 107.0(5) . . ?
C3 C2 H2 126.5 . . ?
N2 C3 H3 126.2 . . ?
C2 C3 N2 107.6(5) . . ?
C2 C3 H3 126.2 . . ?
N2 C4 H4 107.8 . . ?
N2 C4 C5 110.0(4) . . ?
N2 C4 C9 111.1(5) . . ?
C5 C4 H4 107.8 . . ?
C5 C4 C9 112.1(5) . . ?
C9 C4 H4 107.8 . . ?
C4 C5 H5A 109.7 . . ?
C4 C5 H5B 109.7 . . ?
C4 C5 C6 109.7(5) . . ?
H5A C5 H5B 108.2 . . ?
C6 C5 H5A 109.7 . . ?
C6 C5 H5B 109.7 . . ?
C5 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C7 C6 C5 111.3(5) . . ?
C7 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C8 C7 C6 110.8(5) . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
C7 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
C7 C8 C9 111.7(5) . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C4 C9 C8 109.1(5) . . ?
C4 C9 H9A 109.9 . . ?
C4 C9 H9B 109.9 . . ?
C8 C9 H9A 109.9 . . ?
C8 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
N1 C10 H10 108.3 . . ?
N1 C10 C11 110.1(5) . . ?
N1 C10 C15 109.5(5) . . ?
C11 C10 H10 108.3 . . ?
C11 C10 C15 112.2(5) . . ?
C15 C10 H10 108.3 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 C12 110.5(5) . . ?
H11A C11 H11B 108.1 . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
C11 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C13 C12 C11 111.1(5) . . ?
C13 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
C12 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
C12 C13 C14 111.2(5) . . ?
H13A C13 H13B 108.0 . . ?
C14 C13 H13A 109.4 . . ?
C14 C13 H13B 109.4 . . ?
C13 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
C13 C14 C15 111.7(5) . . ?
H14A C14 H14B 107.9 . . ?
C15 C14 H14A 109.3 . . ?
C15 C14 H14B 109.3 . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
C14 C15 C10 110.5(5) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 S1 C1 N1 -95.3(5) . . . . ?
Br1 S1 C1 N2 87.0(5) . . . . ?
N1 C2 C3 N2 -1.2(6) . . . . ?
N1 C10 C11 C12 -177.7(4) . . . . ?
N1 C10 C15 C14 177.2(5) . . . . ?
N2 C4 C5 C6 178.4(5) . . . . ?
N2 C4 C9 C8 -179.3(5) . . . . ?
C1 N1 C2 C3 -0.2(6) . . . . ?
C1 N1 C10 C11 -123.0(6) . . . . ?
C1 N1 C10 C15 113.2(6) . . . . ?
C1 N2 C3 C2 2.2(6) . . . . ?
C1 N2 C4 C5 -140.9(5) . . . . ?
C1 N2 C4 C9 94.4(6) . . . . ?
C2 N1 C1 S1 -176.4(4) . . . . ?
C2 N1 C1 N2 1.6(6) . . . . ?
C2 N1 C10 C11 55.3(7) . . . . ?
C2 N1 C10 C15 -68.5(7) . . . . ?
C3 N2 C1 S1 175.7(4) . . . . ?
C3 N2 C1 N1 -2.3(6) . . . . ?
C3 N2 C4 C5 39.8(7) . . . . ?
C3 N2 C4 C9 -84.9(7) . . . . ?
C4 N2 C1 S1 -3.8(8) . . . . ?
C4 N2 C1 N1 178.3(5) . . . . ?
C4 N2 C3 C2 -178.4(5) . . . . ?
C4 C5 C6 C7 56.3(7) . . . . ?
C5 C4 C9 C8 57.3(7) . . . . ?
C5 C6 C7 C8 -56.2(7) . . . . ?
C6 C7 C8 C9 56.5(7) . . . . ?
C7 C8 C9 C4 -56.2(7) . . . . ?
C9 C4 C5 C6 -57.5(7) . . . . ?
C10 N1 C1 S1 2.1(8) . . . . ?
C10 N1 C1 N2 -179.9(5) . . . . ?
C10 N1 C2 C3 -178.8(5) . . . . ?
C10 C11 C12 C13 55.9(6) . . . . ?
C11 C10 C15 C14 54.6(7) . . . . ?
C11 C12 C13 C14 -56.5(7) . . . . ?
C12 C13 C14 C15 56.0(7) . . . . ?
C13 C14 C15 C10 -54.6(6) . . . . ?
C15 C10 C11 C12 -55.4(6) . . . . ?

_olex2_date_sample_data_collection 2021-07-20
_olex2_exptl_crystal_mounting_method 'mounted on a LithoLoop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.875
_oxdiff_exptl_absorpt_empirical_full_min 0.494
_vrf_PLAT431_ms351-8             
;
PROBLEM: Short Inter HL..A Contact  Br2      ..S1       .       2.72 Ang.  
RESPONSE: The strong interaction between Br2 and S1 is more likely 
a chalcogen bond.
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ms200
_database_code_depnum_ccdc_archive 'CCDC 2121844'
loop_
_audit_author_name
_audit_author_address
'Marina Saab'
;Ghent University
Belgium
;
_audit_update_record             
;
2021-11-12 deposited with the CCDC.	2022-02-07 downloaded from the CCDC.
;
_audit_creation_date             2020-01-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H24 Br2 N2 Se'
_chemical_formula_sum            'C21 H24 Br2 N2 Se'
_chemical_formula_weight         543.18
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H24 Br2 N2 Se'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           52
_space_group_name_H-M_alt        'P n n a'
_space_group_name_Hall           '-P 2a 2bc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z'
'-x+1/2, y+1/2, -z+1/2'
'x, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z'
'x-1/2, -y-1/2, z-1/2'
'-x, y-1/2, z-1/2'

_cell_length_a                   19.6139(4)
_cell_length_b                   14.3164(3)
_cell_length_c                   7.58200(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2129.03(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4943
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      73.7940
_cell_measurement_theta_min      4.4770
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.829
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.661
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.695
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1072
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-10 -1 3 0.0775
-10 -5 2 0.0623
-12 -1 1 0.0295
2 9 2 0.0612
12 -2 -2 0.0016
-11 -2 -2 0.0210
-5 9 0 0.0487
11 -3 1 0.0197

_exptl_crystal_size_max          0.181
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.052
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-9.9905 -0.7346 3.0253 -0.2314 -0.9661 0.1149
-10.0127 -4.7325 1.7173 -0.1891 -0.7878 0.5862
-12.4042 -0.9849 0.9819 0.1734 -0.9300 0.3242
2.2926 8.5476 1.7151 0.0215 -0.1230 -0.9922
11.7760 -1.9087 -1.5769 -0.1829 0.9831 0.0092
-11.1860 -2.3727 -1.9903 0.5715 -0.5405 0.6174
-4.6627 8.6325 0.2588 0.4826 -0.4587 -0.7462
11.4964 -2.9380 1.4373 -0.7239 0.6859 -0.0738

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10733
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.868
_diffrn_reflns_theta_min         4.509
_diffrn_ambient_temperature      100(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00  60.00  101
  2  ω    -66.00  33.00   1.00    1.00    --  -41.68  38.00  30.00   99
  3  ω     27.00  98.00   1.00    1.00    --   41.68-125.00 -60.00   71
  4  ω     33.00 112.00   1.00    1.00    --  106.01-125.00-120.00   79
  5  ω     80.00 178.00   1.00    1.00    --  106.01  45.00-180.00   98
  6  ω    103.00 178.00   1.00    1.00    --  106.01  77.00 -90.00   75
  7  ω     33.00 112.00   1.00    1.00    --  106.01-125.00  60.00   79
  8  ω     78.00 178.00   1.00    1.00    --  106.01  30.00 -90.00  100
  9  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00-180.00  101
 10  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00 -60.00  101
 11  ω     53.00  78.00   1.00    1.00    --  106.01  15.00  60.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0307374000
_diffrn_orient_matrix_UB_12      0.0443146000
_diffrn_orient_matrix_UB_13      -0.1672196000
_diffrn_orient_matrix_UB_21      0.0683663000
_diffrn_orient_matrix_UB_22      -0.0133032000
_diffrn_orient_matrix_UB_23      -0.0967893000
_diffrn_orient_matrix_UB_31      -0.0233942000
_diffrn_orient_matrix_UB_32      -0.0971862000
_diffrn_orient_matrix_UB_33      -0.0628746000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1802
_reflns_number_total             2137
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.837
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         2137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0255
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0257P)²+2.5202P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0601
_refine_ls_wR_factor_ref         0.0635
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C7(H7)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.87341(2) 0.55783(2) 0.76154(4) 0.02639(10) Uani 1 1 d . . . . .
Se1 Se 0.750000 0.500000 0.73863(4) 0.01715(10) Uani 1 2 d S T P . .
N1 N 0.71183(10) 0.55465(14) 0.3822(3) 0.0176(4) Uani 1 1 d . . . . .
C1 C 0.750000 0.500000 0.4881(4) 0.0158(6) Uani 1 2 d S T P . .
C2 C 0.72597(14) 0.53362(19) 0.2085(3) 0.0238(6) Uani 1 1 d . . . . .
H2 H 0.705616 0.561387 0.107652 0.029 Uiso 1 1 calc R . . . .
C3 C 0.66110(12) 0.62365(18) 0.4316(3) 0.0183(5) Uani 1 1 d . . . . .
C4 C 0.59290(13) 0.60249(18) 0.4002(3) 0.0201(5) Uani 1 1 d . . . . .
C5 C 0.54554(13) 0.6711(2) 0.4421(3) 0.0238(6) Uani 1 1 d . . . . .
H5 H 0.498569 0.658966 0.421913 0.029 Uiso 1 1 calc R . . . .
C6 C 0.56439(14) 0.75678(18) 0.5122(3) 0.0239(6) Uani 1 1 d . . . . .
C7 C 0.63304(14) 0.77529(19) 0.5380(3) 0.0227(6) Uani 1 1 d . . . . .
H7 H 0.646235 0.833987 0.585434 0.027 Uiso 1 1 calc R . . . .
C8 C 0.68337(13) 0.70978(18) 0.4960(3) 0.0204(5) Uani 1 1 d . . . . .
C9 C 0.75793(14) 0.73297(18) 0.5138(4) 0.0262(6) Uani 1 1 d . . . . .
H9A H 0.778357 0.693438 0.605166 0.039 Uiso 1 1 calc GR . . . .
H9B H 0.762988 0.798787 0.546855 0.039 Uiso 1 1 calc GR . . . .
H9C H 0.780967 0.721778 0.401104 0.039 Uiso 1 1 calc GR . . . .
C10 C 0.51154(15) 0.8294(2) 0.5567(4) 0.0320(7) Uani 1 1 d . . . . .
H10A H 0.496309 0.860330 0.448293 0.048 Uiso 1 1 calc GR . . . .
H10B H 0.531395 0.875865 0.636580 0.048 Uiso 1 1 calc GR . . . .
H10C H 0.472540 0.799359 0.614173 0.048 Uiso 1 1 calc GR . . . .
C11 C 0.57129(14) 0.5108(2) 0.3206(4) 0.0277(6) Uani 1 1 d . . . . .
H11A H 0.584119 0.509359 0.195745 0.041 Uiso 1 1 calc GR . . . .
H11B H 0.521760 0.503894 0.331468 0.041 Uiso 1 1 calc GR . . . .
H11C H 0.593936 0.459445 0.382889 0.041 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Se1 2.5641(3) . ?
Se1 C1 1.899(3) . ?
N1 C1 1.348(3) . ?
N1 C2 1.379(3) . ?
N1 C3 1.451(3) . ?
C2 C2 1.347(5) 2_665 ?
C3 C4 1.392(3) . ?
C3 C8 1.396(4) . ?
C4 C5 1.389(4) . ?
C4 C11 1.506(4) . ?
C5 C6 1.387(4) . ?
C6 C7 1.386(4) . ?
C6 C10 1.507(4) . ?
C7 C8 1.398(4) . ?
C8 C9 1.506(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Br1 Se1 Br1 172.233(19) . 2_665 ?
C1 Se1 Br1 93.883(10) . . ?
C1 Se1 Br1 93.884(9) . 2_665 ?
C1 N1 C2 109.3(2) . . ?
C1 N1 C3 128.4(2) . . ?
C2 N1 C3 122.2(2) . . ?
N1 C1 Se1 126.57(14) 2_665 . ?
N1 C1 Se1 126.57(14) . . ?
N1 C1 N1 106.9(3) . 2_665 ?
C2 C2 N1 107.26(14) 2_665 . ?
C4 C3 N1 117.8(2) . . ?
C4 C3 C8 123.5(2) . . ?
C8 C3 N1 118.5(2) . . ?
C3 C4 C11 121.9(2) . . ?
C5 C4 C3 116.7(2) . . ?
C5 C4 C11 121.3(2) . . ?
C6 C5 C4 122.3(2) . . ?
C5 C6 C10 120.9(3) . . ?
C7 C6 C5 118.8(2) . . ?
C7 C6 C10 120.3(3) . . ?
C6 C7 C8 121.7(2) . . ?
C3 C8 C7 116.8(2) . . ?
C3 C8 C9 122.0(2) . . ?
C7 C8 C9 121.1(2) . . ?

_olex2_date_sample_data_collection 2019-10-01
_olex2_exptl_crystal_mounting_method 'mounted on a LithoLoop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.564
_oxdiff_exptl_absorpt_empirical_full_min 0.708
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ms242-1
_database_code_depnum_ccdc_archive 'CCDC 2121846'
loop_
_audit_author_name
_audit_author_address
'Marina Saab'
;Ghent University
Belgium
;
_audit_update_record             
;
2021-11-12 deposited with the CCDC.	2022-02-07 downloaded from the CCDC.
;
_audit_creation_date             2020-02-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H40 Br2 N2 Se, C H2 Cl2'
_chemical_formula_sum            'C30 H42 Br2 Cl2 N2 Se'
_chemical_formula_weight         740.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C29 H40 Br2 N2 Se'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.7087(3)
_cell_length_b                   12.5412(3)
_cell_length_c                   15.1640(3)
_cell_angle_alpha                77.201(2)
_cell_angle_beta                 77.009(2)
_cell_angle_gamma                73.293(2)
_cell_volume                     1698.62(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    15223
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      72.9860
_cell_measurement_theta_min      2.9950
_shelx_estimated_absorpt_T_max   0.759
_shelx_estimated_absorpt_T_min   0.464
_exptl_absorpt_coefficient_mu    5.846
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.819
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             748
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 -1 8 0.0414
3 8 -1 0.0255
-6 -5 -4 0.0216
6 1 1 0.0046
-1 6 6 0.0396

_exptl_crystal_size_max          0.155
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.05
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
3.9924 -0.6914 7.7762 0.1930 0.8041 -0.5623
2.6935 7.5921 -0.7191 -0.1655 -0.6941 -0.7006
-5.6335 -5.2487 -4.4496 -0.1425 -0.0102 0.9897
6.2086 1.2885 0.9157 0.6983 0.0546 -0.7137
-1.1875 6.2129 5.5545 -0.9113 -0.0728 -0.4053

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            38991
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.854
_diffrn_reflns_theta_min         3.034
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00  33.00   1.00    1.00    --  -41.68  38.00  60.00   99
  2  ω    -74.00  34.00   1.00    1.00    --  -41.68  77.00 150.00  108
  3  ω   -116.00 -17.00   1.00    1.00    --  -41.68 -38.00-120.00   99
  4  ω     27.00  98.00   1.00    1.00    --   41.68-125.00-150.00   71
  5  ω     23.00 107.00   1.00    1.20    --  106.01 -94.00  90.00   84
  6  ω     33.00 112.00   1.00    1.20    --  106.01-125.00  30.00   79
  7  ω    103.00 178.00   1.00    1.20    --  106.01  77.00 -60.00   75
  8  ω    103.00 178.00   1.00    1.20    --  106.01  77.00-180.00   75
  9  ω     23.00 107.00   1.00    1.20    --  106.01 -94.00 150.00   84
 10  ω    103.00 178.00   1.00    1.20    --  106.01  77.00 -90.00   75
 11  ω     77.00 178.00   1.00    1.20    --  106.01  61.00 -30.00  101
 12  ω     33.00 112.00   1.00    1.20    --  106.01-125.00 -60.00   79
 13  ω     34.00 135.00   1.00    1.20    --  106.01 -61.00-180.00  101
 14  ω    103.00 178.00   1.00    1.20    --  106.01  77.00-120.00   75
 15  ω     80.00 178.00   1.00    1.20    --  106.01  45.00-120.00   98
 16  ω     37.00 127.00   1.00    1.20    --  106.01-144.00  81.38   90
 17  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00  60.00  101
 18  ω   -116.00 -17.00   1.00    1.00    --  -41.68 -38.00 120.00   99
 19  ω      7.00  34.00   1.00    1.00    --   41.68  83.00-136.75   27
 20  ω      8.00  42.00   1.00    1.00    --   41.68  81.00  25.85   34
 21  ω     77.00 178.00   1.00    1.20    --  106.01  61.00  90.00  101
 22  ω     77.00 178.00   1.00    1.20    --  106.01  61.00   0.00  101
 23  ω     80.00 178.00   1.00    1.20    --  106.01  45.00-180.00   98
 24  ω     80.00 178.00   1.00    1.20    --  106.01  45.00-150.00   98
 25  ω     53.00 178.00   1.00    1.20    --  106.01  15.00 120.00  125
 26  ω     77.00 178.00   1.00    1.20    --  106.01  62.00  38.33  101
 27  ω     77.00 178.00   1.00    1.20    --  106.01  61.00 120.00  101
 28  ω     76.00 178.00   1.00    1.20    --  106.01  64.00 -81.09  102
 29  ω      9.00  42.00   1.00    1.00    --   41.68  80.00  49.66   33
 30  ω      6.00  83.00   1.00    1.00    --   41.68 -99.00 -90.00   77
 31  ω      7.00  33.00   1.00    1.00    --   41.68  84.00 -81.64   26
 32  ω      9.00  42.00   1.00    1.00    --   41.68  80.00 -35.25   33
 33  ω     77.00 178.00   1.00    1.20    --  106.01  61.00-180.00  101
 34  ω     74.00 178.00   1.00    1.20    --  106.01  73.00 130.42  104
 35  ω     77.00 178.00   1.00    1.20    --  106.01  61.00-120.00  101
 36  ω     77.00 178.00   1.00    1.20    --  106.01  61.00 -90.00  101
 37  ω     77.00 178.00   1.00    1.20    --  106.01  61.00 -60.00  101
 38  ω     77.00 178.00   1.00    1.20    --  106.01  61.00-150.00  101
 39  ω     77.00 178.00   1.00    1.20    --  106.01  61.00  21.36  101
 40  ω     77.00 178.00   1.00    1.20    --  106.01  61.00  60.00  101
 41  ω      9.00  42.00   1.00    1.00    --   41.68  80.00 152.99   33
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1355836000
_diffrn_orient_matrix_UB_12      -0.0747762000
_diffrn_orient_matrix_UB_13      -0.0514391000
_diffrn_orient_matrix_UB_21      0.0140371000
_diffrn_orient_matrix_UB_22      -0.0880344000
_diffrn_orient_matrix_UB_23      0.0883701000
_diffrn_orient_matrix_UB_31      -0.0985339000
_diffrn_orient_matrix_UB_32      -0.0598831000
_diffrn_orient_matrix_UB_33      -0.0270473000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5918
_reflns_number_total             6767
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.568
_refine_diff_density_min         -0.628
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         6767
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0288
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0321P)²+1.3234P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0678
_refine_ls_wR_factor_ref         0.0706
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12), C15(H15), C24(H24), C27(H27)
2.b Secondary CH2 refined with riding coordinates:
 C30(H30A,H30B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C20(H20), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C),
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C25(H25A,H25B,H25C), C26(H26A,H26B,
 H26C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.35162(3) 0.80761(2) 0.79337(2) 0.02678(7) Uani 1 1 d . . . . .
Br2 Br 0.75035(3) 0.53782(2) 0.60210(2) 0.02729(7) Uani 1 1 d . . . . .
Se1 Se 0.56101(3) 0.67774(2) 0.70001(2) 0.02007(7) Uani 1 1 d . . . . .
N1 N 0.7889(2) 0.79529(15) 0.67739(12) 0.0183(4) Uani 1 1 d . . . . .
N2 N 0.7908(2) 0.66488(15) 0.79922(12) 0.0189(4) Uani 1 1 d . . . . .
C1 C 0.7158(2) 0.72017(18) 0.73039(14) 0.0180(4) Uani 1 1 d . . . . .
C2 C 0.9159(2) 0.70223(19) 0.78754(15) 0.0201(5) Uani 1 1 d . . . . .
C3 C 0.9142(2) 0.78471(19) 0.71165(15) 0.0199(4) Uani 1 1 d . . . . .
C4 C 1.0215(3) 0.8536(2) 0.66945(16) 0.0254(5) Uani 1 1 d . . . . .
H4A H 1.099324 0.813008 0.626410 0.038 Uiso 1 1 calc GR . . . .
H4B H 1.063665 0.867137 0.717661 0.038 Uiso 1 1 calc GR . . . .
H4C H 0.972165 0.926008 0.636494 0.038 Uiso 1 1 calc GR . . . .
C5 C 1.0301(3) 0.6524(2) 0.84667(16) 0.0262(5) Uani 1 1 d . . . . .
H5A H 0.984379 0.625969 0.909123 0.039 Uiso 1 1 calc GR . . . .
H5B H 1.079651 0.709804 0.848063 0.039 Uiso 1 1 calc GR . . . .
H5C H 1.101458 0.588616 0.821682 0.039 Uiso 1 1 calc GR . . . .
C6 C 0.7368(2) 0.59815(19) 0.88567(14) 0.0199(5) Uani 1 1 d . . . . .
C7 C 0.7739(2) 0.48057(19) 0.89652(15) 0.0205(5) Uani 1 1 d . . . . .
C8 C 0.7268(3) 0.4225(2) 0.98346(16) 0.0241(5) Uani 1 1 d . . . . .
H8 H 0.749065 0.342367 0.993443 0.029 Uiso 1 1 calc R . . . .
C9 C 0.6494(3) 0.4787(2) 1.05449(16) 0.0257(5) Uani 1 1 d . . . . .
H9 H 0.618442 0.437417 1.112571 0.031 Uiso 1 1 calc R . . . .
C10 C 0.6165(3) 0.5950(2) 1.04143(16) 0.0256(5) Uani 1 1 d . . . . .
H10 H 0.563447 0.632919 1.091129 0.031 Uiso 1 1 calc R . . . .
C11 C 0.6594(3) 0.6583(2) 0.95692(15) 0.0216(5) Uani 1 1 d . . . . .
C12 C 0.6280(3) 0.7857(2) 0.94831(16) 0.0263(5) Uani 1 1 d . . . . .
H12 H 0.639712 0.818398 0.881437 0.032 Uiso 1 1 calc R . . . .
C13 C 0.7363(3) 0.8189(2) 0.98948(19) 0.0343(6) Uani 1 1 d . . . . .
H13A H 0.726392 0.788469 1.055305 0.051 Uiso 1 1 calc GR . . . .
H13B H 0.716019 0.901402 0.980472 0.051 Uiso 1 1 calc GR . . . .
H13C H 0.835888 0.788135 0.959106 0.051 Uiso 1 1 calc GR . . . .
C14 C 0.4725(3) 0.8383(2) 0.99282(19) 0.0341(6) Uani 1 1 d . . . . .
H14A H 0.403110 0.811848 0.970385 0.051 Uiso 1 1 calc GR . . . .
H14B H 0.452396 0.920738 0.976946 0.051 Uiso 1 1 calc GR . . . .
H14C H 0.462221 0.815927 1.059650 0.051 Uiso 1 1 calc GR . . . .
C15 C 0.8641(3) 0.4137(2) 0.82248(16) 0.0248(5) Uani 1 1 d . . . . .
H15 H 0.884374 0.468080 0.764984 0.030 Uiso 1 1 calc R . . . .
C16 C 1.0104(3) 0.3441(2) 0.85040(19) 0.0341(6) Uani 1 1 d . . . . .
H16A H 1.059942 0.394018 0.865440 0.051 Uiso 1 1 calc GR . . . .
H16B H 1.071827 0.307166 0.799417 0.051 Uiso 1 1 calc GR . . . .
H16C H 0.992996 0.286669 0.904179 0.051 Uiso 1 1 calc GR . . . .
C17 C 0.7829(3) 0.3364(2) 0.80260(17) 0.0301(5) Uani 1 1 d . . . . .
H17A H 0.768387 0.278928 0.856916 0.045 Uiso 1 1 calc GR . . . .
H17B H 0.840246 0.299430 0.750711 0.045 Uiso 1 1 calc GR . . . .
H17C H 0.687770 0.381113 0.787427 0.045 Uiso 1 1 calc GR . . . .
C18 C 0.7396(2) 0.88577(19) 0.60327(15) 0.0197(5) Uani 1 1 d . . . . .
C19 C 0.8014(2) 0.87433(19) 0.51180(15) 0.0209(5) Uani 1 1 d . . . . .
C20 C 0.7567(3) 0.9669(2) 0.44461(15) 0.0230(5) Uani 1 1 d . . . . .
H20 H 0.795732 0.962199 0.381860 0.028 Uiso 1 1 calc R . . . .
C21 C 0.6576(3) 1.0648(2) 0.46671(16) 0.0251(5) Uani 1 1 d . . . . .
H21 H 0.628139 1.125866 0.419573 0.030 Uiso 1 1 calc R . . . .
C22 C 0.6015(3) 1.0737(2) 0.55792(16) 0.0246(5) Uani 1 1 d . . . . .
H22 H 0.533964 1.141616 0.572659 0.030 Uiso 1 1 calc R . . . .
C23 C 0.6416(3) 0.98538(19) 0.62859(15) 0.0212(5) Uani 1 1 d . . . . .
C24 C 0.5843(3) 1.0020(2) 0.72812(16) 0.0254(5) Uani 1 1 d . . . . .
H24 H 0.580408 0.926247 0.765779 0.030 Uiso 1 1 calc R . . . .
C25 C 0.6891(3) 1.0465(3) 0.76368(18) 0.0349(6) Uani 1 1 d . . . . .
H25A H 0.786229 0.994226 0.757073 0.052 Uiso 1 1 calc GR . . . .
H25B H 0.653132 1.052722 0.828576 0.052 Uiso 1 1 calc GR . . . .
H25C H 0.694932 1.120991 0.728150 0.052 Uiso 1 1 calc GR . . . .
C26 C 0.4313(3) 1.0794(2) 0.74306(18) 0.0308(6) Uani 1 1 d . . . . .
H26A H 0.434486 1.157151 0.715070 0.046 Uiso 1 1 calc GR . . . .
H26B H 0.394115 1.075747 0.809048 0.046 Uiso 1 1 calc GR . . . .
H26C H 0.366680 1.055097 0.714679 0.046 Uiso 1 1 calc GR . . . .
C27 C 0.9133(3) 0.7709(2) 0.48124(15) 0.0245(5) Uani 1 1 d . . . . .
H27 H 0.928514 0.710938 0.536403 0.029 Uiso 1 1 calc R . . . .
C28 C 1.0602(3) 0.7986(2) 0.43652(17) 0.0316(6) Uani 1 1 d . . . . .
H28A H 1.049416 0.850877 0.378514 0.047 Uiso 1 1 calc GR . . . .
H28B H 1.133796 0.728951 0.424580 0.047 Uiso 1 1 calc GR . . . .
H28C H 1.090927 0.833776 0.477924 0.047 Uiso 1 1 calc GR . . . .
C29 C 0.8591(3) 0.7252(2) 0.41309(16) 0.0312(6) Uani 1 1 d . . . . .
H29A H 0.924572 0.651894 0.402175 0.047 Uiso 1 1 calc GR . . . .
H29B H 0.857914 0.778353 0.355006 0.047 Uiso 1 1 calc GR . . . .
H29C H 0.760230 0.716115 0.438555 0.047 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.32050(9) 0.61630(6) 0.59079(6) 0.04988(19) Uani 1 1 d . . . . .
Cl2 Cl 0.35506(11) 0.40981(8) 0.72546(5) 0.0602(2) Uani 1 1 d . . . . .
C30 C 0.3970(3) 0.4697(2) 0.61009(18) 0.0356(6) Uani 1 1 d . . . . .
H30A H 0.359807 0.433665 0.571600 0.043 Uiso 1 1 calc R . . . .
H30B H 0.504353 0.454519 0.591399 0.043 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Se1 2.5718(4) . ?
Br2 Se1 2.5952(4) . ?
Se1 C1 1.906(2) . ?
N1 C1 1.353(3) . ?
N1 C3 1.389(3) . ?
N1 C18 1.464(3) . ?
N2 C1 1.353(3) . ?
N2 C2 1.386(3) . ?
N2 C6 1.467(3) . ?
C2 C3 1.366(3) . ?
C2 C5 1.492(3) . ?
C3 C4 1.488(3) . ?
C6 C7 1.395(3) . ?
C6 C11 1.404(3) . ?
C7 C8 1.404(3) . ?
C7 C15 1.511(3) . ?
C8 C9 1.375(4) . ?
C9 C10 1.379(4) . ?
C10 C11 1.395(3) . ?
C11 C12 1.519(3) . ?
C12 C13 1.526(4) . ?
C12 C14 1.529(4) . ?
C15 C16 1.534(3) . ?
C15 C17 1.527(4) . ?
C18 C19 1.403(3) . ?
C18 C23 1.406(3) . ?
C19 C20 1.400(3) . ?
C19 C27 1.519(3) . ?
C20 C21 1.379(3) . ?
C21 C22 1.385(3) . ?
C22 C23 1.393(3) . ?
C23 C24 1.525(3) . ?
C24 C25 1.531(4) . ?
C24 C26 1.523(3) . ?
C27 C28 1.536(3) . ?
C27 C29 1.534(4) . ?
Cl1 C30 1.759(3) . ?
Cl2 C30 1.750(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Br1 Se1 Br2 173.650(13) . . ?
C1 Se1 Br1 96.35(7) . . ?
C1 Se1 Br2 89.97(7) . . ?
C1 N1 C3 109.24(17) . . ?
C1 N1 C18 127.44(19) . . ?
C3 N1 C18 122.81(18) . . ?
C1 N2 C2 109.38(17) . . ?
C1 N2 C6 126.94(19) . . ?
C2 N2 C6 121.98(18) . . ?
N1 C1 Se1 126.04(15) . . ?
N1 C1 N2 107.25(19) . . ?
N2 C1 Se1 125.51(16) . . ?
N2 C2 C5 123.64(19) . . ?
C3 C2 N2 107.01(19) . . ?
C3 C2 C5 129.3(2) . . ?
N1 C3 C4 123.73(19) . . ?
C2 C3 N1 107.1(2) . . ?
C2 C3 C4 129.2(2) . . ?
C7 C6 N2 120.1(2) . . ?
C7 C6 C11 123.3(2) . . ?
C11 C6 N2 116.4(2) . . ?
C6 C7 C8 116.6(2) . . ?
C6 C7 C15 124.27(19) . . ?
C8 C7 C15 119.1(2) . . ?
C9 C8 C7 121.7(2) . . ?
C8 C9 C10 120.0(2) . . ?
C9 C10 C11 121.5(2) . . ?
C6 C11 C12 124.0(2) . . ?
C10 C11 C6 116.9(2) . . ?
C10 C11 C12 119.1(2) . . ?
C11 C12 C13 111.4(2) . . ?
C11 C12 C14 112.6(2) . . ?
C13 C12 C14 109.3(2) . . ?
C7 C15 C16 110.2(2) . . ?
C7 C15 C17 111.5(2) . . ?
C17 C15 C16 110.1(2) . . ?
C19 C18 N1 119.4(2) . . ?
C19 C18 C23 123.0(2) . . ?
C23 C18 N1 117.28(19) . . ?
C18 C19 C27 125.1(2) . . ?
C20 C19 C18 116.5(2) . . ?
C20 C19 C27 118.4(2) . . ?
C21 C20 C19 122.0(2) . . ?
C20 C21 C22 119.7(2) . . ?
C21 C22 C23 121.6(2) . . ?
C18 C23 C24 123.3(2) . . ?
C22 C23 C18 117.1(2) . . ?
C22 C23 C24 119.6(2) . . ?
C23 C24 C25 110.7(2) . . ?
C26 C24 C23 113.6(2) . . ?
C26 C24 C25 109.7(2) . . ?
C19 C27 C28 111.0(2) . . ?
C19 C27 C29 110.8(2) . . ?
C29 C27 C28 109.4(2) . . ?
Cl2 C30 Cl1 111.92(16) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 0.000 155.9 43.1 ?

_olex2_date_sample_data_collection 2019-11-13
_olex2_exptl_crystal_mounting_method 'mounted on a LithoLoop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.368
_oxdiff_exptl_absorpt_empirical_full_min 0.783
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ms226
_database_code_depnum_ccdc_archive 'CCDC 2121845'
loop_
_audit_author_name
_audit_author_address
'Marina Saab'
;Ghent University
Belgium
;
_audit_update_record             
;
2021-11-12 deposited with the CCDC.	2022-02-07 downloaded from the CCDC.
;
_audit_creation_date             2020-01-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H26 Br2 N2 Se'
_chemical_formula_sum            'C21 H26 Br2 N2 Se'
_chemical_formula_weight         545.20
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H26 Br2 N2 Se'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           41
_space_group_name_H-M_alt        'A e a 2'
_space_group_name_Hall           'A 2 -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/2, -y+1, z+1/2'
'-x+1/2, y+1, z+1/2'

_cell_length_a                   18.5263(6)
_cell_length_b                   15.6201(6)
_cell_length_c                   7.3666(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2131.77(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2798
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      73.5340
_cell_measurement_theta_min      4.7570
_shelx_estimated_absorpt_T_max   0.521
_shelx_estimated_absorpt_T_min   0.408
_exptl_absorpt_coefficient_mu    6.821
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64417
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light orange'
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.699
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            5586
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.899
_diffrn_reflns_theta_min         4.774
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -17.00   1.00    2.00    --  -41.68 -38.00   0.00   99
  2  ω      6.00  83.00   1.00    2.00    --   41.68 -99.00-150.00   77
  3  ω     33.00 112.00   1.00    2.00    --  106.01-125.00-150.00   79
  4  ω    103.00 178.00   1.00    2.00    --  106.01  77.00-150.00   75
  5  ω     33.00 112.00   1.00    2.00    --  106.01-125.00 150.00   79
  6  ω     24.00 159.00   1.00    2.00    --  106.01 -15.00 -90.00  135
  7  ω   -115.00 -14.00   1.00    2.00    --  -41.68 -57.00 120.00  101
  8  ω   -115.00 -14.00   1.00    2.00    --  -41.68 -57.00-120.00  101
  9  ω    103.00 178.00   1.00    2.00    --  106.01  77.00  60.00   75
 10  ω     53.00 128.00   1.00    2.00    --  106.01  15.00   0.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0603614000
_diffrn_orient_matrix_UB_12      0.0052942000
_diffrn_orient_matrix_UB_13      0.0795140000
_diffrn_orient_matrix_UB_21      0.1963897000
_diffrn_orient_matrix_UB_22      0.0178042000
_diffrn_orient_matrix_UB_23      -0.0245389000
_diffrn_orient_matrix_UB_31      -0.0394464000
_diffrn_orient_matrix_UB_32      0.0967521000
_diffrn_orient_matrix_UB_33      -0.0000320000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_full    0.907
_reflns_Friedel_fraction_max     0.851
_reflns_number_gt                1775
_reflns_number_total             2000
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.707
_refine_diff_density_min         -0.606
_refine_diff_density_rms         0.104
_refine_ls_abs_structure_details 
;
 Flack x determined using 682 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     122
_refine_ls_number_reflns         2000
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0392
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0531P)²+3.7499P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.1008
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.60856(4) 0.39887(5) 0.78673(11) 0.0307(2) Uani 1 1 d . . . . .
Se1 Se 0.500000 0.500000 0.77615(16) 0.0239(3) Uani 1 2 d S T P . .
N1 N 0.4469(4) 0.4685(5) 0.4145(8) 0.0261(16) Uani 1 1 d . . . . .
C1 C 0.500000 0.500000 0.5130(13) 0.022(2) Uani 1 2 d S T P . .
C2 C 0.4679(5) 0.4688(7) 0.2205(10) 0.032(2) Uani 1 1 d . . . . .
H2A H 0.428112 0.489908 0.142644 0.039 Uiso 1 1 calc R . . . .
H2B H 0.482543 0.411050 0.179238 0.039 Uiso 1 1 calc R . . . .
C3 C 0.3799(4) 0.4286(6) 0.4652(10) 0.0281(18) Uani 1 1 d . . . . .
C4 C 0.3804(5) 0.3440(6) 0.5325(11) 0.0325(19) Uani 1 1 d . . . . .
C5 C 0.3124(7) 0.3049(7) 0.5600(12) 0.039(3) Uani 1 1 d . . . . .
H5 H 0.310497 0.248632 0.608636 0.046 Uiso 1 1 calc R . . . .
C6 C 0.2500(8) 0.3455(5) 0.5190(14) 0.0368(19) Uani 1 1 d . . . . .
C7 C 0.2512(5) 0.4286(6) 0.4494(10) 0.0334(19) Uani 1 1 d . . . . .
H7 H 0.207053 0.456513 0.420799 0.040 Uiso 1 1 calc R . . . .
C8 C 0.3164(4) 0.4710(6) 0.4216(9) 0.0276(17) Uani 1 1 d . . . . .
C9 C 0.3160(5) 0.5599(6) 0.3415(11) 0.0326(19) Uani 1 1 d . . . . .
H9A H 0.316399 0.555984 0.208733 0.049 Uiso 1 1 calc GR . . . .
H9B H 0.358886 0.591109 0.382601 0.049 Uiso 1 1 calc GR . . . .
H9C H 0.272509 0.590254 0.381156 0.049 Uiso 1 1 calc GR . . . .
C10 C 0.1762(7) 0.3026(8) 0.5430(13) 0.046(3) Uani 1 1 d . . . . .
H10A H 0.161153 0.307018 0.670200 0.069 Uiso 1 1 calc GR . . . .
H10B H 0.179612 0.242147 0.508587 0.069 Uiso 1 1 calc GR . . . .
H10C H 0.140597 0.331275 0.465564 0.069 Uiso 1 1 calc GR . . . .
C11 C 0.4496(5) 0.2948(7) 0.5694(12) 0.044(2) Uani 1 1 d . . . . .
H11A H 0.486773 0.312552 0.482650 0.067 Uiso 1 1 calc GR . . . .
H11B H 0.440474 0.233308 0.556150 0.067 Uiso 1 1 calc GR . . . .
H11C H 0.466093 0.306758 0.693216 0.067 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Se1 2.5586(7) . ?
Se1 C1 1.939(9) . ?
N1 C1 1.318(9) . ?
N1 C2 1.481(10) . ?
N1 C3 1.439(11) . ?
C2 C2 1.538(19) 2_665 ?
C3 C4 1.411(13) . ?
C3 C8 1.387(12) . ?
C4 C5 1.415(15) . ?
C4 C11 1.519(13) . ?
C5 C6 1.35(2) . ?
C6 C7 1.396(13) . ?
C6 C10 1.533(19) . ?
C7 C8 1.394(12) . ?
C8 C9 1.508(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Br1 Se1 Br1 176.51(7) 2_665 . ?
C1 Se1 Br1 91.75(3) . . ?
C1 Se1 Br1 91.74(3) . 2_665 ?
C1 N1 C2 109.5(6) . . ?
C1 N1 C3 131.5(6) . . ?
C3 N1 C2 118.6(7) . . ?
N1 C1 Se1 123.4(4) 2_665 . ?
N1 C1 Se1 123.4(4) . . ?
N1 C1 N1 113.2(9) 2_665 . ?
N1 C2 C2 101.8(5) . 2_665 ?
C4 C3 N1 119.4(8) . . ?
C8 C3 N1 117.7(8) . . ?
C8 C3 C4 122.3(8) . . ?
C3 C4 C5 116.6(8) . . ?
C3 C4 C11 122.9(8) . . ?
C5 C4 C11 120.5(9) . . ?
C6 C5 C4 121.8(9) . . ?
C5 C6 C7 120.3(12) . . ?
C5 C6 C10 122.1(8) . . ?
C7 C6 C10 117.6(13) . . ?
C8 C7 C6 120.6(10) . . ?
C3 C8 C7 118.3(8) . . ?
C3 C8 C9 122.3(8) . . ?
C7 C8 C9 119.4(8) . . ?

_olex2_date_sample_data_collection 2019-10-23
_olex2_exptl_crystal_mounting_method 'mounted on a nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.789
_oxdiff_exptl_absorpt_empirical_full_min 0.570
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ms297
_database_code_depnum_ccdc_archive 'CCDC 2121854'
loop_
_audit_author_name
_audit_author_address
'Marina Saab'
;Ghent University
Belgium
;
_audit_update_record             
;
2021-11-12 deposited with the CCDC.	2022-02-07 downloaded from the CCDC.
;
_audit_creation_date             2020-09-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H38 Cl2 N2 Se'
_chemical_formula_sum            'C27 H38 Cl2 N2 Se'
_chemical_formula_weight         540.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C27 H38 Cl2 N2 Se'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   19.3439(3)
_cell_length_b                   12.9998(2)
_cell_length_c                   21.4322(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5389.49(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7953
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      73.6800
_cell_measurement_theta_min      4.1030
_shelx_estimated_absorpt_T_max   0.739
_shelx_estimated_absorpt_T_min   0.425
_exptl_absorpt_coefficient_mu    3.826
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.561
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             2256
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
8 -2 10 0.0128
5 7 -5 0.1001
-8 2 -10 0.0810
-10 -5 -1 0.0998
4 -7 7 0.0712
4 0 -13 0.0505
-3 7 -8 0.0932
-4 0 13 0.0279
3 0 14 0.0452

_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.084
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
8.3576 -1.8956 9.9015 0.1501 0.6295 0.7624
5.0203 7.0960 -5.0519 0.1477 0.6140 -0.7754
-7.8901 2.3539 -10.1014 -0.1378 -0.5781 -0.8042
-9.6092 -5.3772 -1.2904 -0.2254 -0.9402 0.2552
3.7387 -6.8685 6.9312 0.2553 -0.0601 0.9650
4.0921 -0.1632 -13.1395 0.7838 -0.1883 -0.5918
-3.2645 6.6229 -7.8148 -0.1800 0.0421 -0.9828
-3.6432 -0.4175 13.2841 -0.7364 0.1770 0.6530
2.9627 0.2463 13.5076 -0.4068 0.5925 0.6954

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            26447
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.906
_diffrn_reflns_theta_min         4.125
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -70.00  31.00   1.00    1.00    --  -41.68  57.00 -90.00  101
  2  ω     17.00 116.00   1.00    1.00    --   41.68  38.00 120.00   99
  3  ω    103.00 178.00   1.00    5.00    --  106.01  77.00 -90.00   75
  4  ω     33.00 112.00   1.00    5.00    --  106.01-125.00  30.00   79
  5  ω     33.00 132.00   1.00    5.00    --  106.01 -45.00 -90.00   99
  6  ω     80.00 178.00   1.00    5.00    --  106.01  45.00-180.00   98
  7  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00 -90.00  101
  8  ω   -116.00 -17.00   1.00    1.00    --  -41.68 -38.00 150.00   99
  9  ω     80.00 178.00   1.00    5.00    --  106.01  45.00   0.00   98
 10  ω     77.00 102.00   1.00    5.00    --  106.01  61.00  60.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0561830000
_diffrn_orient_matrix_UB_12      -0.0485178000
_diffrn_orient_matrix_UB_13      -0.0415526000
_diffrn_orient_matrix_UB_21      0.0548752000
_diffrn_orient_matrix_UB_22      0.0694622000
_diffrn_orient_matrix_UB_23      0.0305579000
_diffrn_orient_matrix_UB_31      0.0130457000
_diffrn_orient_matrix_UB_32      -0.0828080000
_diffrn_orient_matrix_UB_33      0.0501286000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4443
_reflns_number_total             5362
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.846
_refine_diff_density_min         -1.357
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         5362
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0443
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0400P)²+8.3132P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1065
_refine_ls_wR_factor_ref         0.1158
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C13(H13), C22(H22), C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C18(H18), C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C27(H27A,
 H27B,H27C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.63007(2) 0.48953(2) 0.32233(2) 0.03079(11) Uani 1 1 d . . . . .
Cl1 Cl 0.75141(5) 0.48920(7) 0.29890(4) 0.0478(2) Uani 1 1 d . . . . .
Cl2 Cl 0.50923(5) 0.50059(6) 0.34448(4) 0.0391(2) Uani 1 1 d . . . . .
N1 N 0.64031(11) 0.68780(17) 0.26245(10) 0.0202(5) Uani 1 1 d . . . . .
N2 N 0.62329(11) 0.69924(16) 0.36398(10) 0.0170(4) Uani 1 1 d . . . . .
C1 C 0.63270(13) 0.6371(2) 0.31563(12) 0.0197(5) Uani 1 1 d . . . . .
C2 C 0.62333(16) 0.8076(2) 0.34296(13) 0.0255(6) Uani 1 1 d . . . . .
H2A H 0.662681 0.845861 0.361216 0.031 Uiso 1 1 calc R . . . .
H2B H 0.579699 0.842441 0.354607 0.031 Uiso 1 1 calc R . . . .
C3 C 0.63036(15) 0.7995(2) 0.27260(12) 0.0223(5) Uani 1 1 d . . . . .
H3A H 0.588141 0.824402 0.251325 0.027 Uiso 1 1 calc R . . . .
H3B H 0.670653 0.839183 0.257413 0.027 Uiso 1 1 calc R . . . .
C4 C 0.62805(13) 0.67383(19) 0.42958(12) 0.0179(5) Uani 1 1 d . . . . .
C5 C 0.69360(14) 0.6554(2) 0.45533(13) 0.0210(5) Uani 1 1 d . . . . .
C6 C 0.69635(15) 0.6301(2) 0.51842(14) 0.0268(6) Uani 1 1 d . . . . .
H6 H 0.739760 0.614558 0.536877 0.032 Uiso 1 1 calc R . . . .
C7 C 0.63783(16) 0.6271(2) 0.55454(13) 0.0300(6) Uani 1 1 d . . . . .
H7 H 0.641085 0.608537 0.597309 0.036 Uiso 1 1 calc R . . . .
C8 C 0.57419(15) 0.6510(2) 0.52910(13) 0.0259(6) Uani 1 1 d . . . . .
H8 H 0.534195 0.650232 0.554820 0.031 Uiso 1 1 calc R . . . .
C9 C 0.56798(13) 0.6762(2) 0.46592(13) 0.0208(5) Uani 1 1 d . . . . .
C10 C 0.49791(14) 0.7102(2) 0.44111(13) 0.0266(6) Uani 1 1 d . . . . .
H10 H 0.498767 0.705031 0.394565 0.032 Uiso 1 1 calc R . . . .
C11 C 0.48471(18) 0.8234(3) 0.45899(15) 0.0365(7) Uani 1 1 d . . . . .
H11A H 0.477687 0.828527 0.504170 0.055 Uiso 1 1 calc GR . . . .
H11B H 0.443407 0.848390 0.437288 0.055 Uiso 1 1 calc GR . . . .
H11C H 0.524668 0.865234 0.446882 0.055 Uiso 1 1 calc GR . . . .
C12 C 0.43894(16) 0.6436(3) 0.46532(16) 0.0404(8) Uani 1 1 d . . . . .
H12A H 0.395400 0.665906 0.446262 0.061 Uiso 1 1 calc GR . . . .
H12B H 0.435768 0.650495 0.510766 0.061 Uiso 1 1 calc GR . . . .
H12C H 0.447705 0.571503 0.454518 0.061 Uiso 1 1 calc GR . . . .
C13 C 0.76028(14) 0.6696(2) 0.41887(13) 0.0255(6) Uani 1 1 d . . . . .
H13 H 0.749241 0.664935 0.373373 0.031 Uiso 1 1 calc R . . . .
C14 C 0.81485(15) 0.5879(3) 0.43413(15) 0.0340(7) Uani 1 1 d . . . . .
H14A H 0.832619 0.599348 0.476383 0.051 Uiso 1 1 calc GR . . . .
H14B H 0.852934 0.592706 0.404112 0.051 Uiso 1 1 calc GR . . . .
H14C H 0.793895 0.519382 0.431646 0.051 Uiso 1 1 calc GR . . . .
C15 C 0.79008(17) 0.7772(3) 0.43194(18) 0.0401(8) Uani 1 1 d . . . . .
H15A H 0.756729 0.829643 0.418784 0.060 Uiso 1 1 calc GR . . . .
H15B H 0.833278 0.786036 0.408661 0.060 Uiso 1 1 calc GR . . . .
H15C H 0.799212 0.784460 0.476700 0.060 Uiso 1 1 calc GR . . . .
C16 C 0.64863(15) 0.6494(2) 0.19952(12) 0.0228(5) Uani 1 1 d . . . . .
C17 C 0.71380(16) 0.6563(2) 0.17159(14) 0.0291(6) Uani 1 1 d . . . . .
C18 C 0.71943(17) 0.6229(3) 0.10964(14) 0.0354(7) Uani 1 1 d . . . . .
H18 H 0.763243 0.624559 0.089642 0.042 Uiso 1 1 calc R . . . .
C19 C 0.66289(19) 0.5879(2) 0.07726(14) 0.0354(7) Uani 1 1 d . . . . .
H19 H 0.668041 0.565518 0.035313 0.042 Uiso 1 1 calc R . . . .
C20 C 0.59864(17) 0.5849(2) 0.10519(14) 0.0311(6) Uani 1 1 d . . . . .
H20 H 0.559867 0.561071 0.082132 0.037 Uiso 1 1 calc R . . . .
C21 C 0.58995(16) 0.6166(2) 0.16714(13) 0.0245(6) Uani 1 1 d . . . . .
C22 C 0.51744(15) 0.6196(2) 0.19446(13) 0.0262(6) Uani 1 1 d . . . . .
H22 H 0.521428 0.632410 0.240321 0.031 Uiso 1 1 calc R . . . .
C23 C 0.47590(16) 0.7083(2) 0.16551(15) 0.0314(6) Uani 1 1 d . . . . .
H23A H 0.498852 0.773740 0.174742 0.047 Uiso 1 1 calc GR . . . .
H23B H 0.429143 0.708895 0.183115 0.047 Uiso 1 1 calc GR . . . .
H23C H 0.473204 0.698795 0.120214 0.047 Uiso 1 1 calc GR . . . .
C24 C 0.47925(19) 0.5177(2) 0.18503(16) 0.0380(8) Uani 1 1 d . . . . .
H24A H 0.468685 0.508600 0.140654 0.057 Uiso 1 1 calc GR . . . .
H24B H 0.436139 0.518416 0.209044 0.057 Uiso 1 1 calc GR . . . .
H24C H 0.508462 0.460810 0.199360 0.057 Uiso 1 1 calc GR . . . .
C25 C 0.77657(16) 0.7036(3) 0.20229(15) 0.0449(9) Uani 1 1 d . . . . .
H25 H 0.766493 0.712175 0.247758 0.054 Uiso 1 1 calc R . . . .
C26 C 0.79096(19) 0.8099(4) 0.17452(17) 0.0532(11) Uani 1 1 d . . . . .
H26A H 0.804048 0.802635 0.130567 0.080 Uiso 1 1 calc GR . . . .
H26B H 0.828768 0.842763 0.197540 0.080 Uiso 1 1 calc GR . . . .
H26C H 0.749286 0.852469 0.177673 0.080 Uiso 1 1 calc GR . . . .
C27 C 0.8417(2) 0.6364(5) 0.19567(19) 0.0720(17) Uani 1 1 d . . . . .
H27A H 0.833049 0.568475 0.213913 0.108 Uiso 1 1 calc GR . . . .
H27B H 0.880404 0.669245 0.217485 0.108 Uiso 1 1 calc GR . . . .
H27C H 0.853260 0.628663 0.151383 0.108 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 Cl1 2.4004(10) . ?
Se1 Cl2 2.3895(9) . ?
Se1 C1 1.925(3) . ?
N1 C1 1.324(3) . ?
N1 C3 1.480(3) . ?
N1 C16 1.447(3) . ?
N2 C1 1.326(3) . ?
N2 C2 1.479(3) . ?
N2 C4 1.447(3) . ?
C2 C3 1.518(4) . ?
C4 C5 1.403(4) . ?
C4 C9 1.399(4) . ?
C5 C6 1.393(4) . ?
C5 C13 1.519(4) . ?
C6 C7 1.372(4) . ?
C7 C8 1.382(4) . ?
C8 C9 1.398(4) . ?
C9 C10 1.521(4) . ?
C10 C11 1.542(4) . ?
C10 C12 1.523(4) . ?
C13 C14 1.533(4) . ?
C13 C15 1.538(4) . ?
C16 C17 1.398(4) . ?
C16 C21 1.397(4) . ?
C17 C18 1.401(4) . ?
C17 C25 1.512(5) . ?
C18 C19 1.373(5) . ?
C19 C20 1.380(5) . ?
C20 C21 1.400(4) . ?
C21 C22 1.520(4) . ?
C22 C23 1.537(4) . ?
C22 C24 1.530(4) . ?
C25 C26 1.531(6) . ?
C25 C27 1.540(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl2 Se1 Cl1 176.60(3) . . ?
C1 Se1 Cl1 87.73(8) . . ?
C1 Se1 Cl2 88.89(8) . . ?
C1 N1 C3 110.3(2) . . ?
C1 N1 C16 130.0(2) . . ?
C16 N1 C3 119.3(2) . . ?
C1 N2 C2 110.0(2) . . ?
C1 N2 C4 127.7(2) . . ?
C4 N2 C2 120.9(2) . . ?
N1 C1 Se1 124.2(2) . . ?
N1 C1 N2 112.6(2) . . ?
N2 C1 Se1 123.01(19) . . ?
N2 C2 C3 103.7(2) . . ?
N1 C3 C2 103.1(2) . . ?
C5 C4 N2 118.6(2) . . ?
C9 C4 N2 118.9(2) . . ?
C9 C4 C5 122.4(2) . . ?
C4 C5 C13 123.0(2) . . ?
C6 C5 C4 117.2(2) . . ?
C6 C5 C13 119.7(2) . . ?
C7 C6 C5 121.5(3) . . ?
C6 C7 C8 120.4(3) . . ?
C7 C8 C9 120.8(3) . . ?
C4 C9 C10 123.5(2) . . ?
C8 C9 C4 117.5(2) . . ?
C8 C9 C10 118.9(2) . . ?
C9 C10 C11 109.7(2) . . ?
C9 C10 C12 112.5(3) . . ?
C12 C10 C11 109.5(3) . . ?
C5 C13 C14 113.0(2) . . ?
C5 C13 C15 109.6(2) . . ?
C14 C13 C15 109.5(3) . . ?
C17 C16 N1 118.5(3) . . ?
C21 C16 N1 118.6(2) . . ?
C21 C16 C17 122.6(3) . . ?
C16 C17 C18 117.1(3) . . ?
C16 C17 C25 124.3(3) . . ?
C18 C17 C25 118.4(3) . . ?
C19 C18 C17 121.3(3) . . ?
C18 C19 C20 120.5(3) . . ?
C19 C20 C21 120.7(3) . . ?
C16 C21 C20 117.6(3) . . ?
C16 C21 C22 123.4(2) . . ?
C20 C21 C22 118.9(3) . . ?
C21 C22 C23 110.3(2) . . ?
C21 C22 C24 111.9(2) . . ?
C24 C22 C23 110.1(3) . . ?
C17 C25 C26 110.1(3) . . ?
C17 C25 C27 112.8(4) . . ?
C26 C25 C27 109.1(3) . . ?

_olex2_date_sample_data_collection 2020-09-16
_olex2_exptl_crystal_mounting_method 'mounted on a LithoLoop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.825
_oxdiff_exptl_absorpt_empirical_full_min 0.697
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ms295
_database_code_depnum_ccdc_archive 'CCDC 2121853'
loop_
_audit_author_name
_audit_author_address
'Marina Saab'
;Ghent University
Belgium
;
_audit_update_record             
;
2021-11-12 deposited with the CCDC.	2022-02-07 downloaded from the CCDC.
;
_audit_creation_date             2020-02-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H36 Cl2 N2 Se'
_chemical_formula_sum            'C27 H36 Cl2 N2 Se'
_chemical_formula_weight         538.44
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C27 H36 Cl2 N2 Se'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_H-M_alt        'P 43 21 2'
_space_group_name_Hall           'P 4nw 2abw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   14.07600(10)
_cell_length_b                   14.07600(10)
_cell_length_c                   13.5004(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2674.89(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7198
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      73.8430
_cell_measurement_theta_min      4.4130
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.855
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.734
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1120
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 5 5 0.0509
-4 8 -3 0.0933
4 -3 -7 0.0591
3 -7 5 0.0399
-4 6 5 0.0334
7 5 2 0.0345
5 -6 -5 0.0459
-7 -5 -2 0.0624

_exptl_crystal_size_max          0.179
_exptl_crystal_size_mid          0.118
_exptl_crystal_size_min          0.088
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-5.0577 5.0658 5.4449 -0.0137 -0.0535 0.9985
-3.8760 7.5029 -3.3433 0.2010 0.8415 0.5014
4.3852 -3.2900 -7.0089 0.0763 0.3151 -0.9460
3.0643 -6.9828 4.8249 -0.2203 -0.9215 -0.3198
-3.5142 6.2756 5.4047 0.1999 -0.0467 0.9787
7.2015 5.0691 2.3452 0.9718 -0.2326 0.0382
4.8049 -5.6052 -5.1625 -0.0441 0.0094 -0.9990
-7.1743 -5.0950 -2.3701 -0.9716 0.2325 -0.0432

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13122
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.788
_diffrn_reflns_theta_min         4.442
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00  34.00   1.00    1.00    --  -41.68  77.00-180.00  108
  2  ω    -74.00  34.00   1.00    1.00    --  -41.68  77.00-120.00  108
  3  ω    103.00 178.00   1.00    1.00    --  106.01  77.00 -60.00   75
  4  ω    103.00 178.00   1.00    1.00    --  106.01  77.00-150.00   75
  5  ω    103.00 178.00   1.00    1.00    --  106.01  77.00-180.00   75
  6  ω    103.00 178.00   1.00    1.00    --  106.01  77.00  60.00   75
  7  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00 150.00  101
  8  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00 -90.00  101
  9  ω     33.00 112.00   1.00    1.00    --  106.01-125.00  30.00   79
 10  ω    103.00 132.00   1.00    1.00    --  106.01  77.00   0.00   29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0820403000
_diffrn_orient_matrix_UB_12      0.0721106000
_diffrn_orient_matrix_UB_13      0.0065977000
_diffrn_orient_matrix_UB_21      -0.0380816000
_diffrn_orient_matrix_UB_22      0.0511444000
_diffrn_orient_matrix_UB_23      -0.0927843000
_diffrn_orient_matrix_UB_31      -0.0616181000
_diffrn_orient_matrix_UB_32      0.0644751000
_diffrn_orient_matrix_UB_33      0.0661543000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.688
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                2471
_reflns_number_total             2688
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 935 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.024(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2688
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0295
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0371P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0654
_refine_ls_wR_factor_ref         0.0680
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C7(H7)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C14(H14A,H14B,
 H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.53419(2) 0.53419(2) 0.500000 0.01979(13) Uani 1 2 d S T P . .
Cl1 Cl 0.42878(6) 0.63937(6) 0.58763(6) 0.0293(2) Uani 1 1 d . . . . .
N1 N 0.68218(17) 0.65641(16) 0.57803(18) 0.0146(6) Uani 1 1 d . . . . .
C1 C 0.6295(2) 0.6295(2) 0.500000 0.0167(9) Uani 1 2 d S T P . .
C2 C 0.7435(2) 0.7274(2) 0.5485(2) 0.0175(7) Uani 1 1 d . . . . .
H2 H 0.788568 0.759187 0.589083 0.021 Uiso 1 1 calc R . . . .
C3 C 0.6792(2) 0.6176(2) 0.6781(2) 0.0171(6) Uani 1 1 d . . . . .
C4 C 0.7278(2) 0.5330(3) 0.6955(2) 0.0221(7) Uani 1 1 d . . . . .
C5 C 0.7237(3) 0.4963(3) 0.7917(3) 0.0273(8) Uani 1 1 d . . . . .
H5 H 0.755160 0.438346 0.806535 0.033 Uiso 1 1 calc R . . . .
C6 C 0.6747(2) 0.5430(3) 0.8652(3) 0.0288(8) Uani 1 1 d . . . . .
H6 H 0.671632 0.516288 0.929803 0.035 Uiso 1 1 calc R . . . .
C7 C 0.6299(2) 0.6283(3) 0.8459(2) 0.0241(7) Uani 1 1 d . . . . .
H7 H 0.597779 0.660315 0.898066 0.029 Uiso 1 1 calc R . . . .
C8 C 0.6307(2) 0.6684(2) 0.7514(3) 0.0186(7) Uani 1 1 d . . . . .
C9 C 0.5863(2) 0.7647(2) 0.7341(2) 0.0206(7) Uani 1 1 d . . . . .
H9 H 0.572865 0.771281 0.661634 0.025 Uiso 1 1 calc R . . . .
C10 C 0.6549(2) 0.8441(3) 0.7645(3) 0.0297(9) Uani 1 1 d . . . . .
H10A H 0.671667 0.836740 0.834545 0.044 Uiso 1 1 calc GR . . . .
H10B H 0.624438 0.905890 0.754366 0.044 Uiso 1 1 calc GR . . . .
H10C H 0.712619 0.840293 0.724025 0.044 Uiso 1 1 calc GR . . . .
C11 C 0.4925(3) 0.7774(3) 0.7906(3) 0.0317(9) Uani 1 1 d . . . . .
H11A H 0.451128 0.722671 0.778099 0.048 Uiso 1 1 calc GR . . . .
H11B H 0.460852 0.835536 0.768047 0.048 Uiso 1 1 calc GR . . . .
H11C H 0.505555 0.782096 0.861721 0.048 Uiso 1 1 calc GR . . . .
C12 C 0.7904(3) 0.4843(2) 0.6190(3) 0.0274(8) Uani 1 1 d . . . . .
H12 H 0.772464 0.508905 0.552093 0.033 Uiso 1 1 calc R . . . .
C13 C 0.7775(4) 0.3767(3) 0.6186(3) 0.0475(12) Uani 1 1 d . . . . .
H13A H 0.801283 0.350309 0.681077 0.071 Uiso 1 1 calc GR . . . .
H13B H 0.813108 0.349261 0.563186 0.071 Uiso 1 1 calc GR . . . .
H13C H 0.709971 0.361459 0.611417 0.071 Uiso 1 1 calc GR . . . .
C14 C 0.8948(3) 0.5106(4) 0.6383(3) 0.0469(12) Uani 1 1 d . . . . .
H14A H 0.902143 0.579772 0.635404 0.070 Uiso 1 1 calc GR . . . .
H14B H 0.935136 0.481012 0.587809 0.070 Uiso 1 1 calc GR . . . .
H14C H 0.913668 0.487771 0.704002 0.070 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 Cl1 2.4069(8) 7_556 ?
Se1 Cl1 2.4069(8) . ?
Se1 C1 1.896(4) . ?
N1 C1 1.343(3) . ?
N1 C2 1.379(4) . ?
N1 C3 1.458(4) . ?
C2 C2 1.349(6) 7_556 ?
C3 C4 1.394(5) . ?
C3 C8 1.399(4) . ?
C4 C5 1.398(5) . ?
C4 C12 1.521(5) . ?
C5 C6 1.375(5) . ?
C6 C7 1.382(5) . ?
C7 C8 1.395(5) . ?
C8 C9 1.511(4) . ?
C9 C10 1.534(5) . ?
C9 C11 1.535(5) . ?
C12 C13 1.525(5) . ?
C12 C14 1.537(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 Se1 Cl1 179.89(5) . 7_556 ?
C1 Se1 Cl1 90.05(2) . . ?
C1 Se1 Cl1 90.05(2) . 7_556 ?
C1 N1 C2 108.9(3) . . ?
C1 N1 C3 127.2(3) . . ?
C2 N1 C3 123.9(2) . . ?
N1 C1 Se1 126.18(18) . . ?
N1 C1 Se1 126.18(18) 7_556 . ?
N1 C1 N1 107.6(4) . 7_556 ?
C2 C2 N1 107.29(17) 7_556 . ?
C4 C3 N1 117.6(3) . . ?
C4 C3 C8 123.8(3) . . ?
C8 C3 N1 118.6(3) . . ?
C3 C4 C5 116.8(3) . . ?
C3 C4 C12 123.7(3) . . ?
C5 C4 C12 119.3(3) . . ?
C6 C5 C4 121.0(3) . . ?
C5 C6 C7 120.5(3) . . ?
C6 C7 C8 121.3(3) . . ?
C3 C8 C9 123.4(3) . . ?
C7 C8 C3 116.4(3) . . ?
C7 C8 C9 120.1(3) . . ?
C8 C9 C10 110.5(3) . . ?
C8 C9 C11 112.5(3) . . ?
C10 C9 C11 108.9(3) . . ?
C4 C12 C13 112.4(3) . . ?
C4 C12 C14 109.3(3) . . ?
C13 C12 C14 110.7(3) . . ?

_olex2_date_sample_data_collection 2020-02-17
_olex2_exptl_crystal_mounting_method 'mounted on a LithoLoop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.127
_oxdiff_exptl_absorpt_empirical_full_min 0.419
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ms--349
_database_code_depnum_ccdc_archive 'CCDC 2121851'
loop_
_audit_author_name
_audit_author_address
'Marina Saab'
;Ghent University
Belgium
;
_audit_update_record             
;
2021-11-12 deposited with the CCDC.	2022-02-07 downloaded from the CCDC.
;
_audit_creation_date             2021-10-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H40 Br N2 S, Br3'
_chemical_formula_sum            'C29 H40 Br4 N2 S'
_chemical_formula_weight         768.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C29 H40 N2 Se Br2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   9.7651(2)
_cell_length_b                   16.9691(3)
_cell_length_c                   10.1288(2)
_cell_angle_alpha                90
_cell_angle_beta                 110.132(2)
_cell_angle_gamma                90
_cell_volume                     1575.85(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6503
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      73.5340
_cell_measurement_theta_min      4.6330
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.999
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.774
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             768
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 2 1 0.0323
0 -4 6 0.0452
-6 -4 1 0.0731
0 4 -6 0.0162
5 4 -5 0.0167
-3 9 3 0.0478
-4 -6 5 0.0443
3 -9 -3 0.0328

_exptl_crystal_size_max          0.116
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.062
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
5.4177 2.1660 1.0342 0.2133 0.8923 0.3978
0.0022 -3.8324 5.7857 0.1679 0.6988 -0.6953
-5.8619 -4.0157 1.4044 -0.1576 -0.6609 -0.7338
0.1481 3.9319 -5.8165 -0.1637 -0.6812 0.7135
4.5921 3.6169 -5.3822 -0.1817 0.0445 0.9823
-2.8735 8.8654 3.3882 0.9664 -0.2315 -0.1121
-4.0982 -5.9341 4.7985 -0.0452 0.0098 -0.9989
2.6614 -9.1998 -3.1399 -0.9708 0.2325 0.0592

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15068
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.786
_diffrn_reflns_theta_min         4.650
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -130.00  46.00   1.00    1.00    --  -41.68   0.00  60.00  176
  2  ω     27.00  98.00   1.00    1.00    --   41.68-125.00-120.00   71
  3  ω     34.00 135.00   1.00    6.00    --  106.01 -61.00  90.00  101
  4  ω    103.00 178.00   1.00    6.00    --  106.01  77.00-150.00   75
  5  ω    103.00 178.00   1.00    6.00    --  106.01  77.00   0.00   75
  6  ω    103.00 178.00   1.00    6.00    --  106.01  77.00 120.00   75
  7  ω    103.00 178.00   1.00    6.00    --  106.01  77.00 -90.00   75
  8  ω    103.00 178.00   1.00    6.00    --  106.01  77.00 150.00   75
  9  ω    103.00 178.00   1.00    6.00    --  106.01  77.00 -60.00   75
 10  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00 -30.00  101
 11  ω     14.00 115.00   1.00    1.00    --   41.68  57.00 -90.00  101
 12  ω     33.00 112.00   1.00    6.00    --  106.01-125.00 -30.00   79
 13  ω     78.00 178.00   1.00    6.00    --  106.01  30.00-120.00  100
 14  ω     33.00 112.00   1.00    6.00    --  106.01-125.00  90.00   79
 15  ω     78.00 178.00   1.00    6.00    --  106.01  30.00  90.00  100
 16  ω    -87.00  -6.00   1.00    1.00    --  -41.68 125.00  30.00   81
 17  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00  60.00  101
 18  ω     77.00 112.00   1.00    6.00    --  106.01  61.00   0.00   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0064072000
_diffrn_orient_matrix_UB_12      0.0764734000
_diffrn_orient_matrix_UB_13      0.0796819000
_diffrn_orient_matrix_UB_21      0.1513968000
_diffrn_orient_matrix_UB_22      -0.0184981000
_diffrn_orient_matrix_UB_23      0.1084683000
_diffrn_orient_matrix_UB_31      0.0725173000
_diffrn_orient_matrix_UB_32      0.0453291000
_diffrn_orient_matrix_UB_33      -0.0901839000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2866
_reflns_number_total             3254
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.392
_refine_diff_density_min         -0.827
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         3254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0355
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0415P)²+2.9707P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0915
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C13(H13)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,
 H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.35143(5) 0.250000 0.34652(5) 0.01867(12) Uani 1 2 d S T P . .
S1 S 0.55103(10) 0.250000 0.54171(11) 0.0159(2) Uani 1 2 d S T P . .
N1 N 0.7746(3) 0.31395(14) 0.4710(3) 0.0150(5) Uani 1 1 d . . . . .
C1 C 0.6984(4) 0.250000 0.4850(4) 0.0140(7) Uani 1 2 d S T P . .
C2 C 0.9015(3) 0.29039(18) 0.4518(3) 0.0186(6) Uani 1 1 d . . . . .
C3 C 1.0151(4) 0.34648(18) 0.4430(4) 0.0240(7) Uani 1 1 d . . . . .
H3A H 1.088628 0.353514 0.536607 0.036 Uiso 1 1 calc GR . . . .
H3B H 0.969734 0.397383 0.407827 0.036 Uiso 1 1 calc GR . . . .
H3C H 1.061630 0.325513 0.378766 0.036 Uiso 1 1 calc GR . . . .
C4 C 0.7285(3) 0.39561(16) 0.4698(3) 0.0155(5) Uani 1 1 d . . . . .
C5 C 0.7835(3) 0.43900(17) 0.5947(3) 0.0171(6) Uani 1 1 d . . . . .
C6 C 0.7407(3) 0.51781(18) 0.5884(3) 0.0197(6) Uani 1 1 d . . . . .
H6 H 0.773490 0.549183 0.671039 0.024 Uiso 1 1 calc R . . . .
C7 C 0.6514(3) 0.55096(17) 0.4637(4) 0.0218(6) Uani 1 1 d . . . . .
H7 H 0.624198 0.604817 0.461673 0.026 Uiso 1 1 calc R . . . .
C8 C 0.6013(3) 0.50647(18) 0.3420(3) 0.0205(6) Uani 1 1 d . . . . .
H8 H 0.541253 0.530472 0.257129 0.025 Uiso 1 1 calc R . . . .
C9 C 0.6376(3) 0.42696(17) 0.3419(3) 0.0174(6) Uani 1 1 d . . . . .
C10 C 0.5825(4) 0.37844(19) 0.2067(3) 0.0217(6) Uani 1 1 d . . . . .
H10 H 0.573027 0.322556 0.233724 0.026 Uiso 1 1 calc R . . . .
C11 C 0.6908(4) 0.3799(2) 0.1278(4) 0.0315(8) Uani 1 1 d . . . . .
H11A H 0.705542 0.434351 0.103515 0.047 Uiso 1 1 calc GR . . . .
H11B H 0.652169 0.348524 0.041600 0.047 Uiso 1 1 calc GR . . . .
H11C H 0.784144 0.357611 0.187669 0.047 Uiso 1 1 calc GR . . . .
C12 C 0.4333(4) 0.4053(2) 0.1093(4) 0.0291(7) Uani 1 1 d . . . . .
H12A H 0.363247 0.402242 0.158893 0.044 Uiso 1 1 calc GR . . . .
H12B H 0.401008 0.371041 0.026292 0.044 Uiso 1 1 calc GR . . . .
H12C H 0.439638 0.459742 0.079827 0.044 Uiso 1 1 calc GR . . . .
C13 C 0.8821(3) 0.40370(19) 0.7322(3) 0.0221(6) Uani 1 1 d . . . . .
H13 H 0.911130 0.349721 0.712246 0.027 Uiso 1 1 calc R . . . .
C14 C 1.0211(4) 0.4523(2) 0.7977(4) 0.0330(8) Uani 1 1 d . . . . .
H14A H 1.070524 0.458810 0.728977 0.049 Uiso 1 1 calc GR . . . .
H14B H 1.086097 0.425035 0.880989 0.049 Uiso 1 1 calc GR . . . .
H14C H 0.995695 0.504198 0.824950 0.049 Uiso 1 1 calc GR . . . .
C15 C 0.7985(4) 0.3956(2) 0.8348(4) 0.0344(8) Uani 1 1 d . . . . .
H15A H 0.768807 0.447964 0.855930 0.052 Uiso 1 1 calc GR . . . .
H15B H 0.861414 0.370851 0.921965 0.052 Uiso 1 1 calc GR . . . .
H15C H 0.711668 0.362956 0.792180 0.052 Uiso 1 1 calc GR . . . .
Br2 Br 0.05976(6) 0.250000 0.10545(7) 0.04355(17) Uani 1 2 d S T P . .
Br3 Br 0.18151(6) 0.250000 -0.08645(5) 0.03082(14) Uani 1 2 d S T P . .
Br4 Br 0.32162(9) 0.250000 -0.25061(7) 0.05031(19) Uani 1 2 d S T P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 S1 2.2484(11) . ?
S1 C1 1.723(4) . ?
N1 C1 1.351(3) . ?
N1 C2 1.379(4) . ?
N1 C4 1.456(4) . ?
C2 C2 1.371(6) 4_565 ?
C2 C3 1.487(4) . ?
C4 C5 1.401(4) . ?
C4 C9 1.399(4) . ?
C5 C6 1.396(4) . ?
C5 C13 1.518(4) . ?
C6 C7 1.383(5) . ?
C7 C8 1.383(5) . ?
C8 C9 1.395(4) . ?
C9 C10 1.528(4) . ?
C10 C11 1.530(5) . ?
C10 C12 1.521(5) . ?
C13 C14 1.531(5) . ?
C13 C15 1.533(5) . ?
Br2 Br3 2.6042(9) . ?
Br3 Br4 2.4906(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 Br1 106.12(15) . . ?
C1 N1 C2 109.7(2) . . ?
C1 N1 C4 125.9(2) . . ?
C2 N1 C4 124.4(2) . . ?
N1 C1 S1 126.05(17) 4_565 . ?
N1 C1 S1 126.05(17) . . ?
N1 C1 N1 106.9(3) 4_565 . ?
N1 C2 C3 123.2(3) . . ?
C2 C2 N1 106.86(16) 4_565 . ?
C2 C2 C3 129.80(17) 4_565 . ?
C5 C4 N1 118.1(3) . . ?
C9 C4 N1 117.7(3) . . ?
C9 C4 C5 124.1(3) . . ?
C4 C5 C13 123.1(3) . . ?
C6 C5 C4 116.5(3) . . ?
C6 C5 C13 120.4(3) . . ?
C7 C6 C5 121.1(3) . . ?
C6 C7 C8 120.7(3) . . ?
C7 C8 C9 121.1(3) . . ?
C4 C9 C10 122.7(3) . . ?
C8 C9 C4 116.6(3) . . ?
C8 C9 C10 120.7(3) . . ?
C9 C10 C11 111.5(3) . . ?
C12 C10 C9 112.6(3) . . ?
C12 C10 C11 109.6(3) . . ?
C5 C13 C14 111.9(3) . . ?
C5 C13 C15 109.9(3) . . ?
C14 C13 C15 110.8(3) . . ?
Br4 Br3 Br2 174.33(3) . . ?

_olex2_date_sample_data_collection 2021-10-05
_olex2_exptl_crystal_mounting_method 'mounted on a LithoLoop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.361
_oxdiff_exptl_absorpt_empirical_full_min 0.791
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_m347
_database_code_depnum_ccdc_archive 'CCDC 2121849'
loop_
_audit_author_name
_audit_author_address
'Marina Saab'
;Ghent University
Belgium
;
_audit_update_record             
;
2021-11-12 deposited with the CCDC.	2022-02-07 downloaded from the CCDC.
;
_audit_creation_date             2020-09-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H24 Br2 N2 S'
_chemical_formula_sum            'C21 H24 Br2 N2 S'
_chemical_formula_weight         496.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H24 Br2 N2 S'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.3863(2)
_cell_length_b                   15.2158(2)
_cell_length_c                   14.1625(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.698(2)
_cell_angle_gamma                90
_cell_volume                     2154.70(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8868
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      73.8220
_cell_measurement_theta_min      4.3300
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.721
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.669
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light orange'
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1000
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 -1 8 0.0348
3 -6 4 0.0944
5 1 -7 0.0270
-1 5 -7 0.0546
-4 0 9 0.0390
-2 -8 -3 0.0758
4 1 -9 0.0248
2 8 3 0.1055
-5 0 -4 0.0673
-4 4 7 0.0374
2 2 7 0.0660

_exptl_crystal_size_max          0.226
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.067
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-4.7996 -1.4888 7.8268 -0.0316 -0.1286 0.9912
3.4475 -5.7601 4.3215 0.2229 0.9318 0.2866
5.2119 0.9051 -7.4632 0.0552 0.2271 -0.9723
-0.9304 5.4969 -6.9062 -0.1757 -0.7360 -0.6538
-3.5615 -0.2109 8.8153 -0.2366 0.0576 0.9699
-2.4711 -8.1918 -2.8289 0.9678 -0.2316 0.0989
3.9048 1.2261 -8.5589 0.1194 -0.0296 -0.9924
2.4738 8.1927 2.8232 -0.9677 0.2316 -0.0996
-4.8897 -0.2510 -4.2859 0.3825 -0.9221 -0.0579
-4.3554 4.1759 7.2281 -0.5452 -0.2973 0.7838
2.2214 2.0247 7.3353 -0.5842 0.6826 0.4392

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20876
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.815
_diffrn_reflns_theta_min         4.354
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -122.00  -1.00   1.00    1.00    --  -41.55 -19.00  30.00  121
  2  ω    -87.00  -6.00   1.00    1.00    --  -41.55 125.00 120.00   81
  3  ω     27.00  98.00   1.00    1.00    --   41.55-125.00 -60.00   71
  4  ω     80.00 178.00   1.00    1.00    --  106.01  45.00 150.00   98
  5  ω     34.00 135.00   1.00    1.00    --  106.01 -61.00   0.00  101
  6  ω    103.00 178.00   1.00    1.00    --  106.01  77.00  60.00   75
  7  ω     97.00 178.00   1.00    1.00    --  106.01 125.00   0.00   81
  8  ω     33.00 112.00   1.00    1.00    --  106.01-125.00 -60.00   79
  9  ω     33.00 112.00   1.00    1.00    --  106.01-125.00-150.00   79
 10  ω     23.00 107.00   1.00    1.00    --  106.01 -94.00 -30.00   84
 11  ω   -114.00 -13.00   1.00    1.00    --  -41.55 -57.00 -30.00  101
 12  ω   -114.00 -13.00   1.00    1.00    --  -41.55 -57.00-120.00  101
 13  ω     13.00 114.00   1.00    1.00    --   41.55  57.00-180.00  101
 14  ω     80.00 178.00   1.00    1.00    --  106.01  45.00-150.00   98
 15  ω     80.00 178.00   1.00    1.00    --  106.01  45.00   0.00   98
 16  ω     78.00 171.00   1.00    1.00    --  106.01  30.00  90.00   93
 17  ω     53.00 178.00   1.00    1.00    --  106.01  15.00 -60.00  125
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0354639000
_diffrn_orient_matrix_UB_12      -0.0924614000
_diffrn_orient_matrix_UB_13      -0.0433758000
_diffrn_orient_matrix_UB_21      0.1368545000
_diffrn_orient_matrix_UB_22      -0.0340770000
_diffrn_orient_matrix_UB_23      0.0610149000
_diffrn_orient_matrix_UB_31      -0.0612611000
_diffrn_orient_matrix_UB_32      -0.0228506000
_diffrn_orient_matrix_UB_33      0.0847280000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3823
_reflns_number_total             4284
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.565
_refine_diff_density_min         -0.430
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         4284
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0269
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0337P)²+0.9040P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0653
_refine_ls_wR_factor_ref         0.0679
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C8(H8), C15(H15), C17(H17)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C19(H19A,H19B,
 H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.33423(2) 0.21427(2) 0.50817(2) 0.02088(7) Uani 1 1 d . . . . .
Br2 Br 0.11893(2) 0.12198(2) 0.43805(2) 0.02862(8) Uani 1 1 d . . . . .
S1 S 0.53917(5) 0.29325(4) 0.57706(4) 0.02118(12) Uani 1 1 d . . . . .
N1 N 0.74349(19) 0.21534(12) 0.52111(14) 0.0198(4) Uani 1 1 d . . . . .
N2 N 0.60514(19) 0.28366(12) 0.40140(14) 0.0190(4) Uani 1 1 d . . . . .
C1 C 0.6288(2) 0.26276(14) 0.49721(17) 0.0192(4) Uani 1 1 d . . . . .
C2 C 0.7925(2) 0.20786(15) 0.44009(18) 0.0237(5) Uani 1 1 d . . . . .
H2 H 0.872336 0.178648 0.437502 0.028 Uiso 1 1 calc R . . . .
C3 C 0.7059(2) 0.24980(15) 0.36510(18) 0.0228(5) Uani 1 1 d . . . . .
H3 H 0.712847 0.255042 0.299820 0.027 Uiso 1 1 calc R . . . .
C4 C 0.4965(2) 0.33794(15) 0.34642(16) 0.0188(4) Uani 1 1 d . . . . .
C5 C 0.5102(2) 0.42908(15) 0.35900(17) 0.0214(5) Uani 1 1 d . . . . .
C6 C 0.4051(2) 0.48054(15) 0.30541(18) 0.0241(5) Uani 1 1 d . . . . .
H6 H 0.411524 0.542612 0.312375 0.029 Uiso 1 1 calc R . . . .
C7 C 0.2910(2) 0.44465(16) 0.24198(17) 0.0238(5) Uani 1 1 d . . . . .
C8 C 0.2840(2) 0.35364(15) 0.23091(17) 0.0209(5) Uani 1 1 d . . . . .
H8 H 0.207203 0.328495 0.186844 0.025 Uiso 1 1 calc R . . . .
C9 C 0.3859(2) 0.29825(14) 0.28236(17) 0.0195(5) Uani 1 1 d . . . . .
C10 C 0.3728(2) 0.20036(15) 0.26755(18) 0.0230(5) Uani 1 1 d . . . . .
H10A H 0.459861 0.172483 0.295326 0.035 Uiso 1 1 calc GR . . . .
H10B H 0.341889 0.187382 0.197250 0.035 Uiso 1 1 calc GR . . . .
H10C H 0.307989 0.177481 0.300444 0.035 Uiso 1 1 calc GR . . . .
C11 C 0.1789(3) 0.50211(17) 0.1851(2) 0.0320(6) Uani 1 1 d . . . . .
H11A H 0.181815 0.505437 0.116618 0.048 Uiso 1 1 calc GR . . . .
H11B H 0.188760 0.561220 0.213665 0.048 Uiso 1 1 calc GR . . . .
H11C H 0.093093 0.477130 0.188008 0.048 Uiso 1 1 calc GR . . . .
C12 C 0.6321(2) 0.46995(16) 0.42749(19) 0.0276(5) Uani 1 1 d . . . . .
H12A H 0.630505 0.459848 0.495499 0.041 Uiso 1 1 calc GR . . . .
H12B H 0.632460 0.533284 0.415006 0.041 Uiso 1 1 calc GR . . . .
H12C H 0.712786 0.443306 0.416547 0.041 Uiso 1 1 calc GR . . . .
C13 C 0.8074(2) 0.17973(15) 0.61698(17) 0.0212(5) Uani 1 1 d . . . . .
C14 C 0.9137(2) 0.22639(15) 0.67695(18) 0.0230(5) Uani 1 1 d . . . . .
C15 C 0.9782(2) 0.18945(16) 0.76710(18) 0.0243(5) Uani 1 1 d . . . . .
H15 H 1.050834 0.219961 0.809716 0.029 Uiso 1 1 calc R . . . .
C16 C 0.9389(2) 0.10891(16) 0.79634(18) 0.0265(5) Uani 1 1 d . . . . .
C17 C 0.8305(2) 0.06580(15) 0.73474(19) 0.0268(5) Uani 1 1 d . . . . .
H17 H 0.802664 0.011230 0.755175 0.032 Uiso 1 1 calc R . . . .
C18 C 0.7614(2) 0.09997(15) 0.64390(19) 0.0245(5) Uani 1 1 d . . . . .
C19 C 0.6436(3) 0.05263(16) 0.5785(2) 0.0326(6) Uani 1 1 d . . . . .
H19A H 0.561304 0.084745 0.577120 0.049 Uiso 1 1 calc GR . . . .
H19B H 0.638356 -0.006823 0.603852 0.049 Uiso 1 1 calc GR . . . .
H19C H 0.654312 0.049089 0.511975 0.049 Uiso 1 1 calc GR . . . .
C20 C 1.0149(3) 0.06998(19) 0.8936(2) 0.0369(6) Uani 1 1 d . . . . .
H20A H 1.105836 0.054997 0.891380 0.055 Uiso 1 1 calc GR . . . .
H20B H 0.969201 0.016806 0.906450 0.055 Uiso 1 1 calc GR . . . .
H20C H 1.019057 0.112888 0.945900 0.055 Uiso 1 1 calc GR . . . .
C21 C 0.9603(3) 0.31259(17) 0.6454(2) 0.0324(6) Uani 1 1 d . . . . .
H21A H 1.010662 0.301670 0.597245 0.049 Uiso 1 1 calc GR . . . .
H21B H 1.017865 0.342578 0.702650 0.049 Uiso 1 1 calc GR . . . .
H21C H 0.882579 0.349578 0.615897 0.049 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Br2 2.5996(3) . ?
Br1 S1 2.4089(6) . ?
S1 C1 1.712(2) . ?
N1 C1 1.355(3) . ?
N1 C2 1.380(3) . ?
N1 C13 1.446(3) . ?
N2 C1 1.350(3) . ?
N2 C3 1.384(3) . ?
N2 C4 1.444(3) . ?
C2 C3 1.352(3) . ?
C4 C5 1.400(3) . ?
C4 C9 1.394(3) . ?
C5 C6 1.390(3) . ?
C5 C12 1.505(3) . ?
C6 C7 1.391(3) . ?
C7 C8 1.393(3) . ?
C7 C11 1.504(3) . ?
C8 C9 1.394(3) . ?
C9 C10 1.505(3) . ?
C13 C14 1.392(3) . ?
C13 C18 1.395(3) . ?
C14 C15 1.390(3) . ?
C14 C21 1.507(3) . ?
C15 C16 1.390(3) . ?
C16 C17 1.388(4) . ?
C16 C20 1.511(3) . ?
C17 C18 1.393(3) . ?
C18 C19 1.503(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
S1 Br1 Br2 177.137(17) . . ?
C1 S1 Br1 100.15(8) . . ?
C1 N1 C2 109.47(19) . . ?
C1 N1 C13 125.70(19) . . ?
C2 N1 C13 124.81(19) . . ?
C1 N2 C3 109.59(19) . . ?
C1 N2 C4 125.45(19) . . ?
C3 N2 C4 124.84(19) . . ?
N1 C1 S1 125.29(18) . . ?
N2 C1 S1 128.06(17) . . ?
N2 C1 N1 106.58(19) . . ?
C3 C2 N1 107.3(2) . . ?
C2 C3 N2 107.1(2) . . ?
C5 C4 N2 117.4(2) . . ?
C9 C4 N2 119.28(19) . . ?
C9 C4 C5 123.3(2) . . ?
C4 C5 C12 122.0(2) . . ?
C6 C5 C4 116.8(2) . . ?
C6 C5 C12 121.2(2) . . ?
C5 C6 C7 122.5(2) . . ?
C6 C7 C8 118.2(2) . . ?
C6 C7 C11 121.2(2) . . ?
C8 C7 C11 120.5(2) . . ?
C7 C8 C9 122.2(2) . . ?
C4 C9 C8 117.0(2) . . ?
C4 C9 C10 123.2(2) . . ?
C8 C9 C10 119.9(2) . . ?
C14 C13 N1 118.0(2) . . ?
C14 C13 C18 123.4(2) . . ?
C18 C13 N1 118.6(2) . . ?
C13 C14 C21 121.9(2) . . ?
C15 C14 C13 117.4(2) . . ?
C15 C14 C21 120.7(2) . . ?
C14 C15 C16 121.5(2) . . ?
C15 C16 C20 119.6(2) . . ?
C17 C16 C15 118.9(2) . . ?
C17 C16 C20 121.5(2) . . ?
C16 C17 C18 122.1(2) . . ?
C13 C18 C19 122.0(2) . . ?
C17 C18 C13 116.6(2) . . ?
C17 C18 C19 121.4(2) . . ?

_olex2_date_sample_data_collection 2020-09-15
_olex2_exptl_crystal_mounting_method 'mounted on a LithoLoop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.516
_oxdiff_exptl_absorpt_empirical_full_min 0.788
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ms348
_database_code_depnum_ccdc_archive 'CCDC 2121850'
loop_
_audit_author_name
_audit_author_address
'Marina Saab'
;Ghent University
Belgium
;
_audit_update_record             
;
2021-11-12 deposited with the CCDC.	2022-02-07 downloaded from the CCDC.
;
_audit_creation_date             2021-04-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C21 H26 Br2 N2 S), C H2 Cl2'
_chemical_formula_sum            'C43 H54 Br4 Cl2 N4 S2'
_chemical_formula_weight         1081.52
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H24 Br2 N2 S'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 1 2/c 1'
_space_group_name_Hall           '-P 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   20.8862(5)
_cell_length_b                   8.13980(10)
_cell_length_c                   13.9252(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.044(2)
_cell_angle_gamma                90
_cell_volume                     2331.13(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8394
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      73.6320
_cell_measurement_theta_min      4.2770
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.367
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.625
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light orange'
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1092
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
13 -2 -1 0.0110
-3 0 -8 0.1137
-13 2 0 0.0560
-7 1 8 0.1147
11 -1 3 0.0248
-7 -4 0 0.0270
-5 4 -3 0.1093
6 5 0 0.0962
-12 -2 0 0.0325

_exptl_crystal_size_max          0.251
_exptl_crystal_size_mid          0.139
_exptl_crystal_size_min          0.071
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
12.7744 -1.6815 -0.6057 0.1053 0.4430 0.8903
-3.3386 0.4441 -8.2072 0.1568 0.6524 -0.7415
-12.5708 1.6552 -0.3406 -0.0830 -0.3499 -0.9331
-6.8531 0.8976 8.3275 -0.2329 -0.9725 0.0091
11.2483 -0.8012 3.4663 -0.1194 0.0296 0.9924
-6.9182 -4.4869 -0.4130 0.9412 -0.2256 -0.2515
-5.3594 4.3457 -3.0200 -0.6339 0.1510 -0.7585
6.0389 4.7084 0.0872 -0.9596 0.2299 0.1624
-12.4627 -1.9245 0.1450 0.5556 -0.4268 -0.7136

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22608
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.916
_diffrn_reflns_theta_min         4.299
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -130.00  46.00   1.00    1.00    --  -41.68   0.00 120.00  176
  2  ω     27.00  98.00   1.00    1.00    --   41.68-125.00-120.00   71
  3  ω    -21.00  74.00   1.00    1.00    --   41.68 -77.00  30.00   95
  4  ω    103.00 178.00   1.00    3.80    --  106.01  77.00 120.00   75
  5  ω    103.00 178.00   1.00    3.80    --  106.01  77.00-150.00   75
  6  ω     97.00 178.00   1.00    3.80    --  106.01 125.00  30.00   81
  7  ω     30.00 139.00   1.00    3.80    --  106.01 -77.00 120.00  109
  8  ω     30.00 134.00   1.00    3.80    --  106.01 -30.00 120.00  104
  9  ω    103.00 178.00   1.00    3.80    --  106.01  77.00 -90.00   75
 10  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00   0.00  101
 11  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00  90.00  101
 12  ω     77.00 178.00   1.00    3.80    --  106.01  61.00-180.00  101
 13  ω     78.00 178.00   1.00    3.80    --  106.01  30.00   0.00  100
 14  ω     23.00 107.00   1.00    3.80    --  106.01 -94.00  30.00   84
 15  ω     77.00 178.00   1.00    3.80    --  106.01  61.00  90.00  101
 16  ω     14.00 115.00   1.00    1.00    --   41.68  57.00-150.00  101
 17  ω     14.00 115.00   1.00    1.00    --   41.68  57.00 -60.00  101
 18  ω     77.00 102.00   1.00    3.80    --  106.01  61.00 -90.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0167485000
_diffrn_orient_matrix_UB_12      -0.1819049000
_diffrn_orient_matrix_UB_13      -0.0221401000
_diffrn_orient_matrix_UB_21      0.0316363000
_diffrn_orient_matrix_UB_22      0.0099594000
_diffrn_orient_matrix_UB_23      -0.0918161000
_diffrn_orient_matrix_UB_31      0.0658533000
_diffrn_orient_matrix_UB_32      -0.0510865000
_diffrn_orient_matrix_UB_33      0.0607955000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3925
_reflns_number_total             4645
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.148
_refine_diff_density_min         -0.710
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4645
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0364
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0532P)²+1.5465P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.1002
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H22A(0.5) H22B(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C22(H22A,H22B)
3.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C15(H15), C17(H17)
3.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C19(H19A,H19B,
 H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.26225(2) 0.21106(4) 0.64025(2) 0.02686(10) Uani 1 1 d . . . . .
Br2 Br 0.18123(2) 0.05345(4) 0.72742(2) 0.03321(11) Uani 1 1 d . . . . .
S1 S 0.33605(4) 0.36322(10) 0.55752(5) 0.02911(18) Uani 1 1 d . . . . .
N1 N 0.23068(13) 0.4092(3) 0.41019(18) 0.0266(5) Uani 1 1 d . . . . .
N2 N 0.32447(13) 0.3597(3) 0.36381(18) 0.0268(5) Uani 1 1 d . . . . .
C1 C 0.29366(16) 0.3773(4) 0.4393(2) 0.0253(6) Uani 1 1 d . . . . .
C2 C 0.27840(17) 0.3681(4) 0.2704(2) 0.0305(7) Uani 1 1 d . . . . .
H2A H 0.274132 0.260052 0.237273 0.037 Uiso 1 1 calc R . . . .
H2B H 0.292353 0.450878 0.226225 0.037 Uiso 1 1 calc R . . . .
C3 C 0.21453(17) 0.4188(4) 0.3021(2) 0.0314(7) Uani 1 1 d . . . . .
H3A H 0.201810 0.531682 0.280161 0.038 Uiso 1 1 calc R . . . .
H3B H 0.178897 0.342164 0.275995 0.038 Uiso 1 1 calc R . . . .
C4 C 0.18508(15) 0.4662(4) 0.4695(2) 0.0259(6) Uani 1 1 d . . . . .
C5 C 0.13573(16) 0.3616(4) 0.4858(2) 0.0274(6) Uani 1 1 d . . . . .
C6 C 0.09225(16) 0.4186(4) 0.5442(2) 0.0300(7) Uani 1 1 d . . . . .
H6 H 0.058251 0.348636 0.556722 0.036 Uiso 1 1 calc R . . . .
C7 C 0.09775(17) 0.5750(5) 0.5840(2) 0.0330(7) Uani 1 1 d . . . . .
C8 C 0.14686(17) 0.6780(4) 0.5636(2) 0.0312(7) Uani 1 1 d . . . . .
H8 H 0.150212 0.786200 0.589616 0.037 Uiso 1 1 calc R . . . .
C9 C 0.19119(16) 0.6261(4) 0.5059(2) 0.0266(6) Uani 1 1 d . . . . .
C10 C 0.2426(2) 0.7431(4) 0.4831(3) 0.0367(8) Uani 1 1 d . . . . .
H10A H 0.285524 0.691569 0.500017 0.055 Uiso 1 1 calc GR . . . .
H10B H 0.241697 0.844159 0.521141 0.055 Uiso 1 1 calc GR . . . .
H10C H 0.234071 0.769613 0.413402 0.055 Uiso 1 1 calc GR . . . .
C11 C 0.05138(19) 0.6338(6) 0.6488(3) 0.0479(10) Uani 1 1 d . . . . .
H11A H 0.061624 0.579145 0.712309 0.072 Uiso 1 1 calc GR . . . .
H11B H 0.006658 0.607410 0.618279 0.072 Uiso 1 1 calc GR . . . .
H11C H 0.055793 0.752917 0.657723 0.072 Uiso 1 1 calc GR . . . .
C12 C 0.12798(18) 0.1906(4) 0.4439(2) 0.0330(7) Uani 1 1 d . . . . .
H12A H 0.101116 0.194568 0.378774 0.050 Uiso 1 1 calc GR . . . .
H12B H 0.106946 0.120415 0.486386 0.050 Uiso 1 1 calc GR . . . .
H12C H 0.170852 0.145590 0.439207 0.050 Uiso 1 1 calc GR . . . .
C13 C 0.39017(16) 0.3004(4) 0.3707(2) 0.0269(6) Uani 1 1 d . . . . .
C14 C 0.40133(17) 0.1315(4) 0.3789(2) 0.0296(7) Uani 1 1 d . . . . .
C15 C 0.46476(18) 0.0770(4) 0.3838(2) 0.0347(7) Uani 1 1 d . . . . .
H15 H 0.473472 -0.037397 0.390606 0.042 Uiso 1 1 calc R . . . .
C16 C 0.51546(18) 0.1829(5) 0.3791(2) 0.0388(8) Uani 1 1 d . . . . .
C17 C 0.50275(18) 0.3498(5) 0.3718(3) 0.0393(8) Uani 1 1 d . . . . .
H17 H 0.537612 0.424034 0.369964 0.047 Uiso 1 1 calc R . . . .
C18 C 0.43998(19) 0.4115(4) 0.3670(2) 0.0337(7) Uani 1 1 d . . . . .
C19 C 0.4269(2) 0.5935(5) 0.3585(3) 0.0486(10) Uani 1 1 d . . . . .
H19A H 0.398924 0.617016 0.295907 0.073 Uiso 1 1 calc GR . . . .
H19B H 0.468124 0.652663 0.362262 0.073 Uiso 1 1 calc GR . . . .
H19C H 0.405147 0.629112 0.411872 0.073 Uiso 1 1 calc GR . . . .
C20 C 0.5838(2) 0.1195(7) 0.3798(3) 0.0574(13) Uani 1 1 d . . . . .
H20A H 0.589720 0.015475 0.415717 0.086 Uiso 1 1 calc GR . . . .
H20B H 0.615343 0.200187 0.411577 0.086 Uiso 1 1 calc GR . . . .
H20C H 0.590378 0.101787 0.312637 0.086 Uiso 1 1 calc GR . . . .
C21 C 0.3464(2) 0.0138(4) 0.3821(3) 0.0416(9) Uani 1 1 d . . . . .
H21A H 0.323230 0.045556 0.434672 0.062 Uiso 1 1 calc GR . . . .
H21B H 0.363704 -0.097596 0.393956 0.062 Uiso 1 1 calc GR . . . .
H21C H 0.316285 0.016770 0.319634 0.062 Uiso 1 1 calc GR . . . .
Cl1 Cl -0.04414(6) 0.22667(17) 0.65516(9) 0.0629(3) Uani 1 1 d . . . . .
C22 C 0.000000 0.1100(8) 0.750000 0.0587(16) Uani 1 2 d S T P . .
H22A H 0.030590 0.038149 0.722644 0.070 Uiso 0.5 1 calc R . . . .
H22B H -0.030592 0.038155 0.777357 0.070 Uiso 0.5 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 Br2 2.5882(5) . ?
Br1 S1 2.4201(8) . ?
S1 C1 1.731(3) . ?
N1 C1 1.333(4) . ?
N1 C3 1.487(4) . ?
N1 C4 1.442(4) . ?
N2 C1 1.333(4) . ?
N2 C2 1.478(4) . ?
N2 C13 1.442(4) . ?
C2 C3 1.532(5) . ?
C4 C5 1.386(5) . ?
C4 C9 1.395(4) . ?
C5 C6 1.399(4) . ?
C5 C12 1.508(5) . ?
C6 C7 1.385(5) . ?
C7 C8 1.392(5) . ?
C7 C11 1.512(5) . ?
C8 C9 1.393(5) . ?
C9 C10 1.511(5) . ?
C13 C14 1.396(5) . ?
C13 C18 1.386(5) . ?
C14 C15 1.387(5) . ?
C14 C21 1.502(5) . ?
C15 C16 1.376(6) . ?
C16 C17 1.384(6) . ?
C16 C20 1.515(5) . ?
C17 C18 1.394(5) . ?
C18 C19 1.508(5) . ?
Cl1 C22 1.753(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
S1 Br1 Br2 178.65(3) . . ?
C1 S1 Br1 102.93(11) . . ?
C1 N1 C3 110.9(2) . . ?
C1 N1 C4 127.1(3) . . ?
C4 N1 C3 120.5(3) . . ?
C1 N2 C2 111.1(3) . . ?
C1 N2 C13 124.6(3) . . ?
C13 N2 C2 122.7(2) . . ?
N1 C1 S1 128.1(2) . . ?
N1 C1 N2 111.5(3) . . ?
N2 C1 S1 120.4(2) . . ?
N2 C2 C3 103.0(2) . . ?
N1 C3 C2 102.8(3) . . ?
C5 C4 N1 118.8(3) . . ?
C5 C4 C9 122.5(3) . . ?
C9 C4 N1 118.7(3) . . ?
C4 C5 C6 117.9(3) . . ?
C4 C5 C12 122.4(3) . . ?
C6 C5 C12 119.6(3) . . ?
C7 C6 C5 121.3(3) . . ?
C6 C7 C8 119.0(3) . . ?
C6 C7 C11 120.8(3) . . ?
C8 C7 C11 120.1(3) . . ?
C7 C8 C9 121.5(3) . . ?
C4 C9 C10 122.4(3) . . ?
C8 C9 C4 117.7(3) . . ?
C8 C9 C10 119.9(3) . . ?
C14 C13 N2 118.6(3) . . ?
C18 C13 N2 119.4(3) . . ?
C18 C13 C14 122.0(3) . . ?
C13 C14 C21 120.9(3) . . ?
C15 C14 C13 117.6(3) . . ?
C15 C14 C21 121.5(3) . . ?
C16 C15 C14 122.2(3) . . ?
C15 C16 C17 118.6(3) . . ?
C15 C16 C20 121.2(4) . . ?
C17 C16 C20 120.2(4) . . ?
C16 C17 C18 121.6(4) . . ?
C13 C18 C17 118.0(3) . . ?
C13 C18 C19 121.1(3) . . ?
C17 C18 C19 120.9(4) . . ?
Cl1 C22 Cl1 114.4(4) . 2_556 ?

_olex2_date_sample_data_collection 2020-09-15
_olex2_exptl_crystal_mounting_method 'mounted on a LithoLoop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.975
_oxdiff_exptl_absorpt_empirical_full_min 0.698
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ms456-3
_database_code_depnum_ccdc_archive 'CCDC 2121856'
loop_
_audit_author_name
_audit_author_address
'Marina Saab'
;Ghent University
Belgium
;
_audit_update_record             
;
2021-11-12 deposited with the CCDC.	2022-02-07 downloaded from the CCDC.
;
_audit_creation_date             2021-10-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C69 H56 Cl2 N2 Se'
_chemical_formula_sum            'C69 H56 Cl2 N2 Se'
_chemical_formula_weight         1063.02
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C69 H56 N2 Se I Cl'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.5501(4)
_cell_length_b                   13.3094(5)
_cell_length_c                   21.9568(9)
_cell_angle_alpha                104.727(3)
_cell_angle_beta                 92.152(3)
_cell_angle_gamma                96.504(3)
_cell_volume                     2955.5(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10547
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      73.7250
_cell_measurement_theta_min      3.4440
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.001
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.804
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light orange'
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1104
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 7 6 0.0414
5 5 -8 0.0743
-5 -5 7 0.0052
1 -1 14 0.0348
5 -5 5 0.0716
-1 0 -14 0.0269
-6 5 -5 0.0280

_exptl_crystal_size_max          0.132
_exptl_crystal_size_mid          0.097
_exptl_crystal_size_min          0.064
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.3291 6.5684 6.1259 0.1303 0.5470 0.8270
4.7797 4.6247 -7.6339 0.2154 0.8980 -0.3836
-4.6873 -4.9769 7.1270 -0.2205 -0.9197 0.3249
1.2377 -0.7248 13.6363 0.6941 -0.1655 0.7006
5.4955 -5.4517 4.9678 0.9101 -0.2183 -0.3522
-0.5180 -0.0151 -13.6322 -0.6002 0.1429 -0.7870
-5.5049 5.4654 -4.8653 -0.9073 0.2176 0.3597

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_av_unetI/netI     0.0583
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            42669
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.011
_diffrn_reflns_theta_min         3.462
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -17.00   1.00    2.80    --  -41.68 -38.00 -90.00   99
  2  ω   -116.00 -17.00   1.00    2.80    --  -41.68 -38.00-180.00   99
  3  ω    -87.00  -6.00   1.00    2.80    --  -41.68 125.00 -30.00   81
  4  ω      7.00  33.00   1.00    2.80    --   41.68  84.00-177.49   26
  5  ω     14.00 115.00   1.00    2.80    --   41.68  57.00 120.00  101
  6  ω     23.00 107.00   1.00    6.00    --  106.01 -94.00  90.00   84
  7  ω     23.00 107.00   1.00    6.00    --  106.01 -94.00 -90.00   84
  8  ω    103.00 178.00   1.00    6.00    --  106.01  77.00 -60.00   75
  9  ω    103.00 178.00   1.00    6.00    --  106.01  77.00  90.00   75
 10  ω     30.00 139.00   1.00    6.00    --  106.01 -77.00-150.00  109
 11  ω    103.00 178.00   1.00    6.00    --  106.01  77.00 150.00   75
 12  ω     23.00 107.00   1.00    6.00    --  106.01 -94.00-180.00   84
 13  ω     33.00 132.00   1.00    6.00    --  106.01 -45.00   0.00   99
 14  ω     53.00 178.00   1.00    6.00    --  106.01  15.00 -90.00  125
 15  ω    103.00 178.00   1.00    6.00    --  106.01  77.00  60.00   75
 16  ω     26.00 108.00   1.00    6.00    --  106.01-102.00  23.20   82
 17  ω    -87.00  -6.00   1.00    2.80    --  -41.68 125.00-180.00   81
 18  ω   -116.00 -17.00   1.00    2.80    --  -41.68 -38.00   0.00   99
 19  ω      8.00  42.00   1.00    2.80    --   41.68  82.00-127.25   34
 20  ω      7.00  34.00   1.00    2.80    --   41.68  83.00  -0.11   27
 21  ω      8.00  42.00   1.00    2.80    --   41.68  82.00  59.68   34
 22  ω     77.00 178.00   1.00    6.00    --  106.01  61.00 150.00  101
 23  ω     75.00 176.00   1.00    6.00    --  106.01  69.00 111.08  101
 24  ω     78.00 178.00   1.00    6.00    --  106.01  30.00  30.00  100
 25  ω     78.00 178.00   1.00    6.00    --  106.01  54.00  56.36  100
 26  ω     77.00 178.00   1.00    6.00    --  106.01  61.00 -90.00  101
 27  ω     77.00 178.00   1.00    6.00    --  106.01  61.00  90.00  101
 28  ω     78.00  80.00   1.00    6.00    --  106.01  56.00 -39.24    2
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1188951000
_diffrn_orient_matrix_UB_12      -0.0110715000
_diffrn_orient_matrix_UB_13      0.0395239000
_diffrn_orient_matrix_UB_21      0.0706900000
_diffrn_orient_matrix_UB_22      0.0991987000
_diffrn_orient_matrix_UB_23      -0.0132799000
_diffrn_orient_matrix_UB_31      -0.0507001000
_diffrn_orient_matrix_UB_32      0.0677931000
_diffrn_orient_matrix_UB_33      0.0595794000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9275
_reflns_number_total             11737
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.953
_refine_diff_density_min         -1.032
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     669
_refine_ls_number_reflns         11737
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0674
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0757P)²+5.2670P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1660
_refine_ls_wR_factor_ref         0.1772
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C69) \\sim Ueq, Uanis(C68) \\sim Ueq, Uanis(C67) \\sim Ueq, Uanis(C66)
\\sim Ueq, Uanis(C65) \\sim Ueq: with sigma of 0.005 and sigma for terminal
atoms of 0.01
3.a Ternary CH refined with riding coordinates:
 C11(H11), C24(H24), C44(H44), C57(H57)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C9(H9), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C26(H26), C27(H27),
  C28(H28), C29(H29), C30(H30), C32(H32), C33(H33), C34(H34), C35(H35),
 C36(H36), C39(H39), C42(H42), C46(H46), C47(H47), C48(H48), C49(H49), C50(H50),
  C52(H52), C53(H53), C54(H54), C55(H55), C56(H56), C59(H59), C60(H60),
 C61(H61), C62(H62), C63(H63), C65(H65), C66(H66), C67(H67), C68(H68), C69(H69)
3.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C41(H41A,H41B,H41C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Se1 Se 0.52923(4) 0.55185(3) 0.68855(2) 0.03287(12) Uani 1 1 d . . . . .
Cl1 Cl 0.45883(11) 0.46164(9) 0.58542(5) 0.0449(2) Uani 1 1 d . . . . .
Cl2 Cl 0.60054(11) 0.64538(9) 0.80058(6) 0.0526(3) Uani 1 1 d . . . . .
N1 N 0.3260(3) 0.4124(2) 0.72045(14) 0.0228(6) Uani 1 1 d . . . . .
N2 N 0.2826(3) 0.5734(2) 0.74326(13) 0.0211(6) Uani 1 1 d . . . . .
C1 C 0.3708(3) 0.5109(3) 0.71921(16) 0.0230(7) Uani 1 1 d . . . . .
C2 C 0.1806(3) 0.5126(3) 0.75958(16) 0.0228(7) Uani 1 1 d . . . . .
H2 H 0.105115 0.536589 0.777177 0.027 Uiso 1 1 calc R . . . .
C3 C 0.2080(3) 0.4135(3) 0.74592(16) 0.0235(7) Uani 1 1 d . . . . .
H3 H 0.155784 0.354746 0.752552 0.028 Uiso 1 1 calc R . . . .
C4 C 0.3867(3) 0.3183(3) 0.69724(17) 0.0236(7) Uani 1 1 d . . . . .
C5 C 0.3365(3) 0.2470(3) 0.64101(16) 0.0228(7) Uani 1 1 d . . . . .
C6 C 0.3963(3) 0.1573(3) 0.61979(17) 0.0257(7) Uani 1 1 d . . . . .
H6 H 0.366064 0.109206 0.580693 0.031 Uiso 1 1 calc R . . . .
C7 C 0.4986(3) 0.1365(3) 0.65416(18) 0.0263(7) Uani 1 1 d . . . . .
C8 C 0.5562(4) 0.0358(3) 0.63193(19) 0.0324(8) Uani 1 1 d . . . . .
H8A H 0.518107 -0.002083 0.589819 0.049 Uiso 1 1 calc GR . . . .
H8B H 0.539262 -0.007599 0.661395 0.049 Uiso 1 1 calc GR . . . .
H8C H 0.648796 0.051855 0.630138 0.049 Uiso 1 1 calc GR . . . .
C9 C 0.5431(3) 0.2081(3) 0.71134(17) 0.0241(7) Uani 1 1 d . . . . .
H9 H 0.612088 0.193754 0.735543 0.029 Uiso 1 1 calc R . . . .
C10 C 0.4887(3) 0.3001(3) 0.73381(17) 0.0234(7) Uani 1 1 d . . . . .
C11 C 0.5336(3) 0.3752(3) 0.79806(17) 0.0246(7) Uani 1 1 d . . . . .
H11 H 0.547317 0.447127 0.791448 0.030 Uiso 1 1 calc R . . . .
C12 C 0.6620(3) 0.3545(3) 0.82436(18) 0.0280(7) Uani 1 1 d . . . . .
C13 C 0.6681(4) 0.2929(3) 0.8666(2) 0.0363(9) Uani 1 1 d . . . . .
H13 H 0.591567 0.261722 0.879314 0.044 Uiso 1 1 calc R . . . .
C14 C 0.7865(4) 0.2768(4) 0.8904(2) 0.0434(10) Uani 1 1 d . . . . .
H14 H 0.789916 0.234819 0.919411 0.052 Uiso 1 1 calc R . . . .
C15 C 0.8973(4) 0.3208(4) 0.8724(2) 0.0459(11) Uani 1 1 d . . . . .
H15 H 0.977644 0.309183 0.888544 0.055 Uiso 1 1 calc R . . . .
C16 C 0.8916(4) 0.3820(4) 0.8307(3) 0.0500(12) Uani 1 1 d . . . . .
H16 H 0.968575 0.412737 0.818103 0.060 Uiso 1 1 calc R . . . .
C17 C 0.7742(4) 0.3994(4) 0.8067(2) 0.0390(9) Uani 1 1 d . . . . .
H17 H 0.771503 0.442175 0.778106 0.047 Uiso 1 1 calc R . . . .
C18 C 0.4341(4) 0.3771(3) 0.84647(18) 0.0298(8) Uani 1 1 d . . . . .
C19 C 0.4451(5) 0.4615(4) 0.89900(19) 0.0451(11) Uani 1 1 d . . . . .
H19 H 0.510357 0.518584 0.902743 0.054 Uiso 1 1 calc R . . . .
C20 C 0.3609(6) 0.4633(6) 0.9465(2) 0.069(2) Uani 1 1 d . . . . .
H20 H 0.369135 0.520968 0.982898 0.083 Uiso 1 1 calc R . . . .
C21 C 0.2657(6) 0.3812(6) 0.9403(3) 0.071(2) Uani 1 1 d . . . . .
H21 H 0.207368 0.383101 0.972408 0.085 Uiso 1 1 calc R . . . .
C22 C 0.2534(5) 0.2965(5) 0.8887(3) 0.0585(15) Uani 1 1 d . . . . .
H22 H 0.187770 0.239839 0.885223 0.070 Uiso 1 1 calc R . . . .
C23 C 0.3377(4) 0.2944(4) 0.8415(2) 0.0369(9) Uani 1 1 d . . . . .
H23 H 0.329513 0.235985 0.805577 0.044 Uiso 1 1 calc R . . . .
C24 C 0.2100(3) 0.2567(3) 0.60835(17) 0.0238(7) Uani 1 1 d . . . . .
H24 H 0.205072 0.333255 0.614632 0.029 Uiso 1 1 calc R . . . .
C25 C 0.1977(3) 0.2071(3) 0.53716(16) 0.0253(7) Uani 1 1 d . . . . .
C26 C 0.2285(4) 0.2681(3) 0.49557(19) 0.0333(8) Uani 1 1 d . . . . .
H26 H 0.258990 0.340411 0.511655 0.040 Uiso 1 1 calc R . . . .
C27 C 0.2152(4) 0.2245(4) 0.4311(2) 0.0414(10) Uani 1 1 d . . . . .
H27 H 0.236226 0.267070 0.403228 0.050 Uiso 1 1 calc R . . . .
C28 C 0.1712(4) 0.1188(4) 0.40671(19) 0.0382(9) Uani 1 1 d . . . . .
H28 H 0.162148 0.089381 0.362339 0.046 Uiso 1 1 calc R . . . .
C29 C 0.1409(4) 0.0571(3) 0.44684(19) 0.0347(8) Uani 1 1 d . . . . .
H29 H 0.111845 -0.015401 0.430345 0.042 Uiso 1 1 calc R . . . .
C30 C 0.1531(4) 0.1011(3) 0.51200(18) 0.0297(8) Uani 1 1 d . . . . .
H30 H 0.130683 0.058397 0.539613 0.036 Uiso 1 1 calc R . . . .
C31 C 0.0980(3) 0.2138(3) 0.64118(16) 0.0247(7) Uani 1 1 d . . . . .
C32 C 0.1092(4) 0.1400(3) 0.67550(18) 0.0294(8) Uani 1 1 d . . . . .
H32 H 0.187085 0.110832 0.676849 0.035 Uiso 1 1 calc R . . . .
C33 C 0.0081(4) 0.1088(3) 0.70762(18) 0.0351(9) Uani 1 1 d . . . . .
H33 H 0.017411 0.058756 0.731047 0.042 Uiso 1 1 calc R . . . .
C34 C -0.1056(4) 0.1495(4) 0.70594(19) 0.0383(9) Uani 1 1 d . . . . .
H34 H -0.173983 0.129083 0.728973 0.046 Uiso 1 1 calc R . . . .
C35 C -0.1199(4) 0.2207(4) 0.6703(2) 0.0383(9) Uani 1 1 d . . . . .
H35 H -0.199164 0.247360 0.667785 0.046 Uiso 1 1 calc R . . . .
C36 C -0.0183(3) 0.2527(3) 0.63839(18) 0.0291(8) Uani 1 1 d . . . . .
H36 H -0.028307 0.301763 0.614378 0.035 Uiso 1 1 calc R . . . .
C37 C 0.2923(3) 0.6865(3) 0.75340(16) 0.0232(7) Uani 1 1 d . . . . .
C38 C 0.3089(3) 0.7506(3) 0.81506(16) 0.0255(7) Uani 1 1 d . . . . .
C39 C 0.3229(4) 0.8581(3) 0.82273(17) 0.0309(8) Uani 1 1 d . . . . .
H39 H 0.337215 0.903166 0.864171 0.037 Uiso 1 1 calc R . . . .
C40 C 0.3166(4) 0.9021(3) 0.77171(18) 0.0314(8) Uani 1 1 d . . . . .
C41 C 0.3286(5) 1.0187(3) 0.7815(2) 0.0455(11) Uani 1 1 d . . . . .
H41A H 0.376435 1.038183 0.747967 0.068 Uiso 1 1 calc GR . . . .
H41B H 0.374132 1.053329 0.822576 0.068 Uiso 1 1 calc GR . . . .
H41C H 0.243232 1.040770 0.780526 0.068 Uiso 1 1 calc GR . . . .
C42 C 0.2920(3) 0.8352(3) 0.71153(17) 0.0270(7) Uani 1 1 d . . . . .
H42 H 0.284837 0.864430 0.676522 0.032 Uiso 1 1 calc R . . . .
C43 C 0.2777(3) 0.7271(3) 0.70086(16) 0.0231(7) Uani 1 1 d . . . . .
C44 C 0.2360(3) 0.6553(3) 0.63555(16) 0.0244(7) Uani 1 1 d . . . . .
H44 H 0.292502 0.598516 0.627597 0.029 Uiso 1 1 calc R . . . .
C45 C 0.2536(4) 0.7115(3) 0.58324(16) 0.0261(7) Uani 1 1 d . . . . .
C46 C 0.1609(4) 0.7669(3) 0.56638(17) 0.0297(8) Uani 1 1 d . . . . .
H46 H 0.083025 0.768741 0.586744 0.036 Uiso 1 1 calc R . . . .
C47 C 0.1808(4) 0.8199(3) 0.51989(18) 0.0337(8) Uani 1 1 d . . . . .
H47 H 0.116253 0.857265 0.508388 0.040 Uiso 1 1 calc R . . . .
C48 C 0.2944(5) 0.8183(4) 0.49033(19) 0.0405(10) Uani 1 1 d . . . . .
H48 H 0.308382 0.855307 0.458951 0.049 Uiso 1 1 calc R . . . .
C49 C 0.3875(5) 0.7628(4) 0.5066(2) 0.0473(11) Uani 1 1 d . . . . .
H49 H 0.465228 0.761178 0.486090 0.057 Uiso 1 1 calc R . . . .
C50 C 0.3677(4) 0.7090(3) 0.5531(2) 0.0371(9) Uani 1 1 d . . . . .
H50 H 0.431851 0.670902 0.564159 0.045 Uiso 1 1 calc R . . . .
C51 C 0.0978(3) 0.6023(3) 0.63229(17) 0.0258(7) Uani 1 1 d . . . . .
C52 C 0.0558(4) 0.5161(3) 0.58217(18) 0.0320(8) Uani 1 1 d . . . . .
H52 H 0.113907 0.490183 0.551750 0.038 Uiso 1 1 calc R . . . .
C53 C -0.0693(4) 0.4670(3) 0.5755(2) 0.0386(10) Uani 1 1 d . . . . .
H53 H -0.096397 0.408929 0.540489 0.046 Uiso 1 1 calc R . . . .
C54 C -0.1544(4) 0.5031(3) 0.6202(2) 0.0374(9) Uani 1 1 d . . . . .
H54 H -0.239690 0.469288 0.616211 0.045 Uiso 1 1 calc R . . . .
C55 C -0.1147(4) 0.5879(3) 0.6703(2) 0.0374(9) Uani 1 1 d . . . . .
H55 H -0.172366 0.612348 0.701262 0.045 Uiso 1 1 calc R . . . .
C56 C 0.0109(4) 0.6387(3) 0.67575(18) 0.0316(8) Uani 1 1 d . . . . .
H56 H 0.036626 0.698791 0.709722 0.038 Uiso 1 1 calc R . . . .
C57 C 0.2952(4) 0.7073(3) 0.87300(16) 0.0268(7) Uani 1 1 d . . . . .
H57 H 0.327118 0.637427 0.862513 0.032 Uiso 1 1 calc R . . . .
C58 C 0.1539(4) 0.6890(3) 0.88584(17) 0.0300(8) Uani 1 1 d . . . . .
C59 C 0.0561(4) 0.7281(3) 0.85798(18) 0.0350(9) Uani 1 1 d . . . . .
H59 H 0.076684 0.770005 0.829717 0.042 Uiso 1 1 calc R . . . .
C60 C -0.0693(4) 0.7072(4) 0.8705(2) 0.0409(10) Uani 1 1 d . . . . .
H60 H -0.134121 0.734390 0.850729 0.049 Uiso 1 1 calc R . . . .
C61 C -0.1018(5) 0.6473(4) 0.9115(2) 0.0498(12) Uani 1 1 d . . . . .
H61 H -0.188773 0.631809 0.919546 0.060 Uiso 1 1 calc R . . . .
C62 C -0.0055(5) 0.6097(4) 0.9410(2) 0.0507(12) Uani 1 1 d . . . . .
H62 H -0.026834 0.569176 0.969987 0.061 Uiso 1 1 calc R . . . .
C63 C 0.1206(4) 0.6306(4) 0.9287(2) 0.0411(10) Uani 1 1 d . . . . .
H63 H 0.185366 0.605038 0.949666 0.049 Uiso 1 1 calc R . . . .
C64 C 0.3747(5) 0.7752(3) 0.93189(19) 0.0414(11) Uani 1 1 d . . . . .
C65 C 0.3230(7) 0.8508(4) 0.9754(2) 0.0633(15) Uani 1 1 d . U . . .
H65 H 0.237083 0.861342 0.967355 0.076 Uiso 1 1 calc R . . . .
C66 C 0.3883(8) 0.9111(6) 1.0292(3) 0.0818(19) Uani 1 1 d . U . . .
H66 H 0.350044 0.964649 1.056881 0.098 Uiso 1 1 calc R . . . .
C67 C 0.4998(9) 0.8949(6) 1.0417(3) 0.083(2) Uani 1 1 d . U . . .
H67 H 0.542387 0.935522 1.080521 0.100 Uiso 1 1 calc R . . . .
C68 C 0.5635(8) 0.8242(7) 1.0041(4) 0.094(2) Uani 1 1 d . U . . .
H68 H 0.648361 0.816029 1.016202 0.112 Uiso 1 1 calc R . . . .
C69 C 0.4988(6) 0.7594(4) 0.9435(3) 0.0679(16) Uani 1 1 d . U . . .
H69 H 0.540406 0.710044 0.914508 0.081 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Se1 Cl1 2.3260(13) . ?
Se1 Cl2 2.5016(14) . ?
Se1 C1 1.900(3) . ?
N1 C1 1.350(4) . ?
N1 C3 1.384(4) . ?
N1 C4 1.456(5) . ?
N2 C1 1.350(5) . ?
N2 C2 1.386(4) . ?
N2 C37 1.455(4) . ?
C2 C3 1.344(5) . ?
C4 C5 1.395(5) . ?
C4 C10 1.398(5) . ?
C5 C6 1.397(5) . ?
C5 C24 1.525(5) . ?
C6 C7 1.387(5) . ?
C7 C8 1.508(5) . ?
C7 C9 1.397(5) . ?
C9 C10 1.396(5) . ?
C10 C11 1.529(5) . ?
C11 C12 1.533(5) . ?
C11 C18 1.519(5) . ?
C12 C13 1.389(5) . ?
C12 C17 1.379(5) . ?
C13 C14 1.395(6) . ?
C14 C15 1.365(7) . ?
C15 C16 1.376(7) . ?
C16 C17 1.394(6) . ?
C18 C19 1.382(6) . ?
C18 C23 1.391(6) . ?
C19 C20 1.393(8) . ?
C20 C21 1.374(10) . ?
C21 C22 1.371(10) . ?
C22 C23 1.387(6) . ?
C24 C25 1.528(5) . ?
C24 C31 1.538(5) . ?
C25 C26 1.392(5) . ?
C25 C30 1.397(5) . ?
C26 C27 1.382(6) . ?
C27 C28 1.389(7) . ?
C28 C29 1.373(6) . ?
C29 C30 1.396(6) . ?
C31 C32 1.394(5) . ?
C31 C36 1.390(5) . ?
C32 C33 1.383(5) . ?
C33 C34 1.374(6) . ?
C34 C35 1.391(6) . ?
C35 C36 1.388(5) . ?
C37 C38 1.398(5) . ?
C37 C43 1.403(5) . ?
C38 C39 1.387(5) . ?
C38 C57 1.529(5) . ?
C39 C40 1.392(5) . ?
C40 C41 1.502(5) . ?
C40 C42 1.389(5) . ?
C42 C43 1.388(5) . ?
C43 C44 1.524(5) . ?
C44 C45 1.527(5) . ?
C44 C51 1.538(5) . ?
C45 C46 1.383(5) . ?
C45 C50 1.395(5) . ?
C46 C47 1.390(5) . ?
C47 C48 1.384(6) . ?
C48 C49 1.382(7) . ?
C49 C50 1.397(6) . ?
C51 C52 1.389(5) . ?
C51 C56 1.384(5) . ?
C52 C53 1.390(6) . ?
C53 C54 1.387(6) . ?
C54 C55 1.373(6) . ?
C55 C56 1.404(6) . ?
C57 C58 1.531(5) . ?
C57 C64 1.531(5) . ?
C58 C59 1.395(5) . ?
C58 C63 1.396(5) . ?
C59 C60 1.374(6) . ?
C60 C61 1.374(6) . ?
C61 C62 1.391(7) . ?
C62 C63 1.379(6) . ?
C64 C65 1.378(8) . ?
C64 C69 1.374(8) . ?
C65 C66 1.359(8) . ?
C66 C67 1.252(11) . ?
C67 C68 1.345(11) . ?
C68 C69 1.483(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 Se1 Cl2 178.37(4) . . ?
C1 Se1 Cl1 91.73(11) . . ?
C1 Se1 Cl2 86.80(11) . . ?
C1 N1 C3 108.7(3) . . ?
C1 N1 C4 127.0(3) . . ?
C3 N1 C4 124.3(3) . . ?
C1 N2 C2 108.7(3) . . ?
C1 N2 C37 126.9(3) . . ?
C2 N2 C37 124.3(3) . . ?
N1 C1 Se1 125.4(3) . . ?
N1 C1 N2 107.5(3) . . ?
N2 C1 Se1 127.0(2) . . ?
C3 C2 N2 107.3(3) . . ?
C2 C3 N1 107.7(3) . . ?
C5 C4 N1 118.7(3) . . ?
C5 C4 C10 122.5(3) . . ?
C10 C4 N1 118.7(3) . . ?
C4 C5 C6 117.6(3) . . ?
C4 C5 C24 121.9(3) . . ?
C6 C5 C24 119.9(3) . . ?
C7 C6 C5 121.9(3) . . ?
C6 C7 C8 120.7(3) . . ?
C6 C7 C9 118.6(3) . . ?
C9 C7 C8 120.6(3) . . ?
C10 C9 C7 121.6(3) . . ?
C4 C10 C11 121.1(3) . . ?
C9 C10 C4 117.7(3) . . ?
C9 C10 C11 121.1(3) . . ?
C10 C11 C12 113.0(3) . . ?
C18 C11 C10 112.8(3) . . ?
C18 C11 C12 110.4(3) . . ?
C13 C12 C11 121.5(3) . . ?
C17 C12 C11 119.4(3) . . ?
C17 C12 C13 119.0(4) . . ?
C12 C13 C14 120.2(4) . . ?
C15 C14 C13 120.6(4) . . ?
C14 C15 C16 119.4(4) . . ?
C15 C16 C17 120.8(4) . . ?
C12 C17 C16 120.0(4) . . ?
C19 C18 C11 118.3(4) . . ?
C19 C18 C23 119.2(4) . . ?
C23 C18 C11 122.4(4) . . ?
C18 C19 C20 120.2(6) . . ?
C21 C20 C19 119.5(6) . . ?
C22 C21 C20 121.2(5) . . ?
C21 C22 C23 119.3(6) . . ?
C22 C23 C18 120.5(5) . . ?
C5 C24 C25 114.3(3) . . ?
C5 C24 C31 109.8(3) . . ?
C25 C24 C31 111.6(3) . . ?
C26 C25 C24 120.2(3) . . ?
C26 C25 C30 118.3(3) . . ?
C30 C25 C24 121.5(3) . . ?
C27 C26 C25 120.6(4) . . ?
C26 C27 C28 120.5(4) . . ?
C29 C28 C27 119.9(4) . . ?
C28 C29 C30 119.7(4) . . ?
C25 C30 C29 120.9(3) . . ?
C32 C31 C24 122.8(3) . . ?
C36 C31 C24 118.7(3) . . ?
C36 C31 C32 118.4(3) . . ?
C33 C32 C31 120.7(4) . . ?
C34 C33 C32 120.6(4) . . ?
C33 C34 C35 119.5(4) . . ?
C36 C35 C34 120.0(4) . . ?
C35 C36 C31 120.7(4) . . ?
C38 C37 N2 119.2(3) . . ?
C38 C37 C43 122.1(3) . . ?
C43 C37 N2 118.6(3) . . ?
C37 C38 C57 122.6(3) . . ?
C39 C38 C37 117.5(3) . . ?
C39 C38 C57 119.4(3) . . ?
C38 C39 C40 122.2(3) . . ?
C39 C40 C41 121.0(4) . . ?
C42 C40 C39 118.3(3) . . ?
C42 C40 C41 120.6(3) . . ?
C43 C42 C40 122.2(3) . . ?
C37 C43 C44 121.2(3) . . ?
C42 C43 C37 117.5(3) . . ?
C42 C43 C44 121.2(3) . . ?
C43 C44 C45 112.6(3) . . ?
C43 C44 C51 111.8(3) . . ?
C45 C44 C51 110.8(3) . . ?
C46 C45 C44 121.6(3) . . ?
C46 C45 C50 119.4(3) . . ?
C50 C45 C44 118.9(3) . . ?
C45 C46 C47 120.6(4) . . ?
C48 C47 C46 120.1(4) . . ?
C49 C48 C47 119.8(4) . . ?
C48 C49 C50 120.2(4) . . ?
C45 C50 C49 119.9(4) . . ?
C52 C51 C44 118.8(3) . . ?
C56 C51 C44 123.1(3) . . ?
C56 C51 C52 118.0(4) . . ?
C51 C52 C53 121.5(4) . . ?
C54 C53 C52 119.8(4) . . ?
C55 C54 C53 119.7(4) . . ?
C54 C55 C56 120.2(4) . . ?
C51 C56 C55 120.9(4) . . ?
C38 C57 C58 110.2(3) . . ?
C38 C57 C64 113.6(3) . . ?
C58 C57 C64 111.3(3) . . ?
C59 C58 C57 124.1(3) . . ?
C59 C58 C63 117.7(4) . . ?
C63 C58 C57 118.2(3) . . ?
C60 C59 C58 121.4(4) . . ?
C59 C60 C61 120.6(4) . . ?
C60 C61 C62 119.0(4) . . ?
C63 C62 C61 120.7(4) . . ?
C62 C63 C58 120.6(4) . . ?
C65 C64 C57 121.2(5) . . ?
C69 C64 C57 120.3(5) . . ?
C69 C64 C65 118.4(5) . . ?
C66 C65 C64 123.6(7) . . ?
C67 C66 C65 118.8(8) . . ?
C66 C67 C68 124.7(7) . . ?
C67 C68 C69 118.7(7) . . ?
C64 C69 C68 115.7(7) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 0.000 456.1 151.1 ?

_olex2_date_sample_data_collection 2021-03-16
_olex2_exptl_crystal_mounting_method 'Mounyted on a LithoLoop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.696
_oxdiff_exptl_absorpt_empirical_full_min 0.672
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ms266
_database_code_depnum_ccdc_archive 'CCDC 2121860'
loop_
_audit_author_name
_audit_author_address
'Marina Saab'
;Ghent University
Belgium
;
_audit_update_record             
;
2021-11-12 deposited with the CCDC.	2022-02-07 downloaded from the CCDC.
;
_audit_creation_date             2020-11-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H26 I2 N2 Se'
_chemical_formula_sum            'C21 H26 I2 N2 Se'
_chemical_formula_weight         639.20
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H26 N2 Se I2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   30.1615(4)
_cell_length_b                   44.2672(7)
_cell_length_c                   18.8321(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.730(2)
_cell_angle_gamma                90
_cell_volume                     24915.5(7)
_cell_formula_units_Z            40
_cell_measurement_reflns_used    15324
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      73.4660
_cell_measurement_theta_min      3.0780
_shelx_estimated_absorpt_T_max   0.322
_shelx_estimated_absorpt_T_min   0.110
_exptl_absorpt_coefficient_mu    21.537
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.718
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.704
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             12240
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
17 5 -7 0.0430
-14 16 7 0.0443
-3 -11 -11 0.0510
9 -13 -10 0.0443
11 24 -1 0.0265
-6 7 -11 0.0603
-12 -22 -1 0.0273
6 -7 11 0.0749
-15 -11 7 0.0246
-2 29 -1 0.0368

_exptl_crystal_size_max          0.184
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.068
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
16.6101 4.9548 -7.4529 0.1766 0.7351 -0.6546
-13.6660 16.0241 6.5890 -0.3329 -0.9418 -0.0460
-3.2771 -10.7715 -10.7728 0.9794 0.1823 0.0870
8.6682 -13.0410 -10.0957 0.6872 0.7250 -0.0463
10.9416 23.8251 -0.6092 -0.3699 0.0874 -0.9250
-5.7538 6.8378 -10.7276 0.8957 -0.2149 -0.3894
-11.8554 -22.1412 -1.4355 0.5337 -0.1268 0.8361
5.5961 -7.1765 10.7337 -0.8902 0.2136 0.4025
-15.3308 -11.0527 7.2029 -0.1387 -0.5762 0.8055
-1.5552 28.5685 -0.7540 -0.1254 -0.5270 -0.8406

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0769
_diffrn_reflns_av_unetI/netI     0.0697
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       48
_diffrn_reflns_limit_k_min       -55
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            119022
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.323
_diffrn_reflns_theta_min         2.957
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -87.00  -6.00   1.00    2.00    --  -41.68 125.00-120.00   81
  2  ω    -87.00  -6.00   1.00    2.00    --  -41.68 125.00-180.00   81
  3  ω   -116.00 -17.00   1.00    2.00    --  -41.68 -38.00  30.00   99
  4  ω    -66.00  33.00   1.00    2.00    --  -41.68  38.00-180.00   99
  5  ω    103.00 178.00   1.00    2.00    --  106.01  77.00-180.00   75
  6  ω    103.00 178.00   1.00    2.00    --  106.01  77.00 -30.00   75
  7  ω     80.00 178.00   1.00    2.00    --  106.01  45.00 -60.00   98
  8  ω     33.00 132.00   1.00    2.00    --  106.01 -45.00  30.00   99
  9  ω     78.00 178.00   1.00    2.00    --  106.01  30.00 -90.00  100
 10  ω     23.00 107.00   1.00    2.00    --  106.01 -94.00  60.00   84
 11  ω   -115.00 -14.00   1.00    2.00    --  -41.68 -57.00-180.00  101
 12  ω   -115.00 -14.00   1.00    2.00    --  -41.68 -57.00 -60.00  101
 13  ω     14.00 115.00   1.00    2.00    --   41.68  57.00 150.00  101
 14  ω     77.00 178.00   1.00    2.00    --  106.01  61.00 150.00  101
 15  ω    103.00 178.00   1.00    2.00    --  106.01  77.00  30.00   75
 16  ω     23.00 107.00   1.00    2.00    --  106.01 -94.00-120.00   84
 17  ω     78.00 122.00   1.00    2.00    --  106.01  30.00  60.00   44
 18  ω    103.00 178.00   1.00    2.00    --  106.01  77.00  90.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0215529000
_diffrn_orient_matrix_UB_12      -0.0075887000
_diffrn_orient_matrix_UB_13      -0.0767687000
_diffrn_orient_matrix_UB_21      0.0430770000
_diffrn_orient_matrix_UB_22      -0.0164603000
_diffrn_orient_matrix_UB_23      -0.0135664000
_diffrn_orient_matrix_UB_31      -0.0183442000
_diffrn_orient_matrix_UB_32      -0.0297031000
_diffrn_orient_matrix_UB_33      0.0272021000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                14544
_reflns_number_total             24869
_reflns_odcompleteness_completeness 99.99
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.143
_refine_diff_density_min         -1.005
_refine_diff_density_rms         0.137
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1201
_refine_ls_number_reflns         24869
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0435
_refine_ls_restrained_S_all      0.949
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0146P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0746
_refine_ls_wR_factor_ref         0.0913
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C104) \\sim Ueq: with sigma of 0.003 and sigma for terminal atoms of 0.006
3.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C23(H23A,H23B), C24(H24A,H24B), C44(H44A,H44B),
 C45(H45A,H45B), C65(H65A,H65B), C66(H66A,H66B), C86(H86A,H86B), C87(H87A,H87B)
3.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C15(H15), C17(H17), C27(H27), C29(H29), C36(H36), C38(H38),
 C48(H48), C50(H50), C57(H57), C59(H59), C69(H69), C71(H71), C78(H78), C80(H80),
  C90(H90), C92(H92), C99(H99), C101(H101)
3.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C19(H19A,H19B,
 H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C31(H31A,H31B,H31C), C32(H32A,
 H32B,H32C), C33(H33A,H33B,H33C), C40(H40A,H40B,H40C), C41(H41A,H41B,H41C),
 C42(H42A,H42B,H42C), C52(H52A,H52B,H52C), C53(H53A,H53B,H53C), C54(H54A,H54B,
 H54C), C61(H61A,H61B,H61C), C62(H62A,H62B,H62C), C63(H63A,H63B,H63C), C73(H73A,
 H73B,H73C), C74(H74A,H74B,H74C), C75(H75A,H75B,H75C), C82(H82A,H82B,H82C),
 C83(H83A,H83B,H83C), C84(H84A,H84B,H84C), C94(H94A,H94B,H94C), C95(H95A,H95B,
 H95C), C96(H96A,H96B,H96C), C103(H10D,H10E,H10F), C104(H10G,H10H,H10I),
 C105(H10J,H10K,H10L)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.60241(2) 0.14739(2) 0.49535(2) 0.02188(10) Uani 1 1 d . . . . .
I2 I 0.56429(2) 0.14025(2) 0.34591(2) 0.02636(11) Uani 1 1 d . . . . .
Se1 Se 0.65104(3) 0.15866(2) 0.62684(4) 0.0317(2) Uani 1 1 d . . . . .
N1 N 0.64585(19) 0.14763(13) 0.7704(3) 0.0205(14) Uani 1 1 d . . . . .
N2 N 0.57846(19) 0.14715(12) 0.7095(3) 0.0183(13) Uani 1 1 d . . . . .
C1 C 0.6216(2) 0.15053(15) 0.7059(4) 0.0213(16) Uani 1 1 d . . . . .
C2 C 0.5701(2) 0.13994(17) 0.7830(3) 0.0226(16) Uani 1 1 d . . . . .
H2A H 0.559596 0.118869 0.786461 0.027 Uiso 1 1 calc R . . . .
H2B H 0.547782 0.153842 0.799152 0.027 Uiso 1 1 calc R . . . .
C3 C 0.6163(2) 0.14440(17) 0.8266(4) 0.0254(17) Uani 1 1 d . . . . .
H3A H 0.617090 0.162762 0.856761 0.030 Uiso 1 1 calc R . . . .
H3B H 0.624992 0.126712 0.857557 0.030 Uiso 1 1 calc R . . . .
C4 C 0.6932(2) 0.15036(16) 0.7846(4) 0.0206(16) Uani 1 1 d . . . . .
C5 C 0.7186(2) 0.12360(17) 0.7878(4) 0.0255(17) Uani 1 1 d . . . . .
C6 C 0.7646(2) 0.12608(18) 0.8049(4) 0.0289(18) Uani 1 1 d . . . . .
H6 H 0.782528 0.108406 0.805963 0.035 Uiso 1 1 calc R . . . .
C7 C 0.7849(3) 0.15363(19) 0.8205(4) 0.033(2) Uani 1 1 d . . . . .
C8 C 0.7594(2) 0.17933(17) 0.8156(4) 0.0291(18) Uani 1 1 d . . . . .
H8 H 0.773725 0.198340 0.824471 0.035 Uiso 1 1 calc R . . . .
C9 C 0.7128(2) 0.17833(17) 0.7978(4) 0.0258(17) Uani 1 1 d . . . . .
C10 C 0.6855(2) 0.20746(17) 0.7916(5) 0.037(2) Uani 1 1 d . . . . .
H10A H 0.704047 0.224129 0.813233 0.056 Uiso 1 1 calc GR . . . .
H10B H 0.659319 0.205050 0.816684 0.056 Uiso 1 1 calc GR . . . .
H10C H 0.675739 0.211914 0.740963 0.056 Uiso 1 1 calc GR . . . .
C11 C 0.8352(2) 0.15549(19) 0.8402(5) 0.038(2) Uani 1 1 d . . . . .
H11A H 0.849463 0.155420 0.796438 0.057 Uiso 1 1 calc GR . . . .
H11B H 0.845672 0.138087 0.869954 0.057 Uiso 1 1 calc GR . . . .
H11C H 0.842906 0.174175 0.866925 0.057 Uiso 1 1 calc GR . . . .
C12 C 0.6963(3) 0.09334(18) 0.7711(5) 0.043(2) Uani 1 1 d . . . . .
H12A H 0.677015 0.088583 0.807534 0.065 Uiso 1 1 calc GR . . . .
H12B H 0.719208 0.077665 0.771028 0.065 Uiso 1 1 calc GR . . . .
H12C H 0.678152 0.094173 0.723841 0.065 Uiso 1 1 calc GR . . . .
C13 C 0.5409(2) 0.15144(16) 0.6541(4) 0.0173(15) Uani 1 1 d . . . . .
C14 C 0.5222(2) 0.12664(15) 0.6179(4) 0.0188(15) Uani 1 1 d . . . . .
C15 C 0.4835(2) 0.13075(16) 0.5688(3) 0.0195(15) Uani 1 1 d . . . . .
H15 H 0.469257 0.113710 0.544905 0.023 Uiso 1 1 calc R . . . .
C16 C 0.4653(2) 0.15964(16) 0.5543(4) 0.0204(16) Uani 1 1 d . . . . .
C17 C 0.4858(2) 0.18393(16) 0.5916(4) 0.0227(16) Uani 1 1 d . . . . .
H17 H 0.473625 0.203552 0.582464 0.027 Uiso 1 1 calc R . . . .
C18 C 0.5241(2) 0.18054(16) 0.6425(3) 0.0193(15) Uani 1 1 d . . . . .
C19 C 0.5444(2) 0.20687(16) 0.6854(4) 0.0268(17) Uani 1 1 d . . . . .
H19A H 0.574225 0.210964 0.672570 0.040 Uiso 1 1 calc GR . . . .
H19B H 0.546741 0.202116 0.736552 0.040 Uiso 1 1 calc GR . . . .
H19C H 0.525373 0.224711 0.674934 0.040 Uiso 1 1 calc GR . . . .
C20 C 0.4243(2) 0.16377(17) 0.5004(4) 0.0285(18) Uani 1 1 d . . . . .
H20A H 0.433279 0.167189 0.452879 0.043 Uiso 1 1 calc GR . . . .
H20B H 0.407298 0.181216 0.513871 0.043 Uiso 1 1 calc GR . . . .
H20C H 0.405688 0.145601 0.499172 0.043 Uiso 1 1 calc GR . . . .
C21 C 0.5411(2) 0.09523(16) 0.6317(4) 0.0264(17) Uani 1 1 d . . . . .
H21A H 0.522184 0.080623 0.602534 0.040 Uiso 1 1 calc GR . . . .
H21B H 0.541842 0.090239 0.682513 0.040 Uiso 1 1 calc GR . . . .
H21C H 0.571526 0.094451 0.618879 0.040 Uiso 1 1 calc GR . . . .
I3 I 0.87895(2) 0.24688(2) 0.97367(2) 0.02008(9) Uani 1 1 d . . . . .
I4 I 0.91142(2) 0.24267(2) 1.12775(2) 0.02581(10) Uani 1 1 d . . . . .
Se2 Se 0.83688(2) 0.25318(2) 0.83495(3) 0.02106(16) Uani 1 1 d . . . . .
N3 N 0.92001(15) 0.24639(13) 0.7760(2) 0.0174(12) Uani 1 1 d . . . . .
N4 N 0.85984(15) 0.24614(14) 0.6971(2) 0.0187(12) Uani 1 1 d . . . . .
C22 C 0.87602(19) 0.24834(15) 0.7661(3) 0.0174(13) Uani 1 1 d . . . . .
C23 C 0.89618(19) 0.24391(18) 0.6517(3) 0.0238(16) Uani 1 1 d . . . . .
H23A H 0.896919 0.261903 0.620692 0.029 Uiso 1 1 calc R . . . .
H23B H 0.892982 0.225541 0.621500 0.029 Uiso 1 1 calc R . . . .
C24 C 0.9378(2) 0.24224(18) 0.7077(3) 0.0244(16) Uani 1 1 d . . . . .
H24A H 0.952848 0.222419 0.706082 0.029 Uiso 1 1 calc R . . . .
H24B H 0.959328 0.258439 0.700074 0.029 Uiso 1 1 calc R . . . .
C25 C 0.95158(18) 0.25089(15) 0.8397(3) 0.0151(13) Uani 1 1 d . . . . .
C26 C 0.9696(2) 0.22558(15) 0.8763(3) 0.0172(14) Uani 1 1 d . . . . .
C27 C 1.0051(2) 0.23013(15) 0.9322(3) 0.0171(14) Uani 1 1 d . . . . .
H27 H 1.018234 0.213179 0.957925 0.021 Uiso 1 1 calc R . . . .
C28 C 1.0211(2) 0.25876(16) 0.9505(3) 0.0183(14) Uani 1 1 d . . . . .
C29 C 1.0006(2) 0.28363(15) 0.9138(4) 0.0210(15) Uani 1 1 d . . . . .
H29 H 1.010420 0.303420 0.927776 0.025 Uiso 1 1 calc R . . . .
C30 C 0.9661(2) 0.27997(16) 0.8573(4) 0.0182(15) Uani 1 1 d . . . . .
C31 C 0.9457(2) 0.30682(16) 0.8160(4) 0.0264(17) Uani 1 1 d . . . . .
H31A H 0.950396 0.305070 0.765692 0.040 Uiso 1 1 calc GR . . . .
H31B H 0.959772 0.325390 0.836404 0.040 Uiso 1 1 calc GR . . . .
H31C H 0.913497 0.307474 0.819063 0.040 Uiso 1 1 calc GR . . . .
C32 C 1.0602(2) 0.26301(17) 1.0085(3) 0.0255(17) Uani 1 1 d . . . . .
H32A H 1.077909 0.280477 0.996931 0.038 Uiso 1 1 calc GR . . . .
H32B H 1.079026 0.244874 1.011808 0.038 Uiso 1 1 calc GR . . . .
H32C H 1.049191 0.266451 1.054441 0.038 Uiso 1 1 calc GR . . . .
C33 C 0.9516(2) 0.19448(15) 0.8590(4) 0.0256(16) Uani 1 1 d . . . . .
H33A H 0.920612 0.193318 0.869143 0.038 Uiso 1 1 calc GR . . . .
H33B H 0.969869 0.179615 0.888295 0.038 Uiso 1 1 calc GR . . . .
H33C H 0.952476 0.190183 0.808112 0.038 Uiso 1 1 calc GR . . . .
C34 C 0.81360(18) 0.25062(16) 0.6655(3) 0.0167(14) Uani 1 1 d . . . . .
C35 C 0.7882(2) 0.22465(16) 0.6453(4) 0.0222(15) Uani 1 1 d . . . . .
C36 C 0.7447(2) 0.22932(19) 0.6115(4) 0.0301(19) Uani 1 1 d . . . . .
H36 H 0.726056 0.212366 0.598439 0.036 Uiso 1 1 calc R . . . .
C37 C 0.7280(2) 0.2582(2) 0.5966(4) 0.0327(19) Uani 1 1 d . . . . .
C38 C 0.7545(2) 0.28320(18) 0.6165(4) 0.0303(18) Uani 1 1 d . . . . .
H38 H 0.742534 0.302883 0.607163 0.036 Uiso 1 1 calc R . . . .
C39 C 0.7985(2) 0.27986(17) 0.6501(4) 0.0261(17) Uani 1 1 d . . . . .
C40 C 0.8274(3) 0.30714(18) 0.6682(4) 0.038(2) Uani 1 1 d . . . . .
H40A H 0.843577 0.304950 0.716589 0.057 Uiso 1 1 calc GR . . . .
H40B H 0.808558 0.325253 0.665976 0.057 Uiso 1 1 calc GR . . . .
H40C H 0.848842 0.309017 0.633697 0.057 Uiso 1 1 calc GR . . . .
C41 C 0.6806(2) 0.2623(2) 0.5588(5) 0.053(3) Uani 1 1 d . . . . .
H41A H 0.677937 0.253081 0.511196 0.080 Uiso 1 1 calc GR . . . .
H41B H 0.673827 0.283964 0.554003 0.080 Uiso 1 1 calc GR . . . .
H41C H 0.659435 0.252701 0.586950 0.080 Uiso 1 1 calc GR . . . .
C42 C 0.8070(3) 0.19333(17) 0.6574(4) 0.036(2) Uani 1 1 d . . . . .
H42A H 0.825296 0.188401 0.619719 0.054 Uiso 1 1 calc GR . . . .
H42B H 0.782430 0.178776 0.656106 0.054 Uiso 1 1 calc GR . . . .
H42C H 0.825563 0.192412 0.704230 0.054 Uiso 1 1 calc GR . . . .
I5 I 0.60194(2) 0.34778(2) 0.49507(2) 0.02157(10) Uani 1 1 d . . . . .
I6 I 0.56498(2) 0.34327(2) 0.34458(2) 0.02821(11) Uani 1 1 d . . . . .
Se3 Se 0.65147(3) 0.35646(2) 0.62696(4) 0.0298(2) Uani 1 1 d . . . . .
N5 N 0.64541(19) 0.34808(13) 0.7706(3) 0.0207(13) Uani 1 1 d . . . . .
N6 N 0.57814(19) 0.34602(13) 0.7095(3) 0.0189(13) Uani 1 1 d . . . . .
C43 C 0.6212(2) 0.34969(15) 0.7060(4) 0.0170(15) Uani 1 1 d . . . . .
C44 C 0.5702(2) 0.34048(17) 0.7846(3) 0.0225(16) Uani 1 1 d . . . . .
H44A H 0.559645 0.319599 0.790870 0.027 Uiso 1 1 calc R . . . .
H44B H 0.548070 0.354892 0.799411 0.027 Uiso 1 1 calc R . . . .
C45 C 0.6167(2) 0.34560(17) 0.8269(4) 0.0230(17) Uani 1 1 d . . . . .
H45A H 0.617433 0.364364 0.855618 0.028 Uiso 1 1 calc R . . . .
H45B H 0.625675 0.328362 0.859072 0.028 Uiso 1 1 calc R . . . .
C46 C 0.6933(2) 0.35073(16) 0.7859(4) 0.0183(15) Uani 1 1 d . . . . .
C47 C 0.7186(2) 0.32440(16) 0.7916(4) 0.0229(16) Uani 1 1 d . . . . .
C48 C 0.7647(2) 0.32787(17) 0.8097(4) 0.0291(18) Uani 1 1 d . . . . .
H48 H 0.783079 0.310398 0.811878 0.035 Uiso 1 1 calc R . . . .
C49 C 0.7847(2) 0.35569(17) 0.8245(4) 0.0293(19) Uani 1 1 d . . . . .
C50 C 0.7582(2) 0.38102(18) 0.8159(4) 0.0302(18) Uani 1 1 d . . . . .
H50 H 0.771794 0.400348 0.823017 0.036 Uiso 1 1 calc R . . . .
C51 C 0.7119(2) 0.37916(16) 0.7970(4) 0.0250(17) Uani 1 1 d . . . . .
C52 C 0.6841(3) 0.40778(17) 0.7899(4) 0.036(2) Uani 1 1 d . . . . .
H52A H 0.664381 0.407562 0.744083 0.054 Uiso 1 1 calc GR . . . .
H52B H 0.703996 0.425369 0.791560 0.054 Uiso 1 1 calc GR . . . .
H52C H 0.666094 0.408928 0.829327 0.054 Uiso 1 1 calc GR . . . .
C53 C 0.8350(3) 0.35774(19) 0.8458(5) 0.044(2) Uani 1 1 d . . . . .
H53A H 0.845296 0.340208 0.875274 0.066 Uiso 1 1 calc GR . . . .
H53B H 0.842170 0.376294 0.873364 0.066 Uiso 1 1 calc GR . . . .
H53C H 0.849833 0.358039 0.802680 0.066 Uiso 1 1 calc GR . . . .
C54 C 0.6977(2) 0.29395(17) 0.7760(4) 0.0339(19) Uani 1 1 d . . . . .
H54A H 0.676441 0.289840 0.809881 0.051 Uiso 1 1 calc GR . . . .
H54B H 0.721056 0.278423 0.780921 0.051 Uiso 1 1 calc GR . . . .
H54C H 0.681885 0.293692 0.727001 0.051 Uiso 1 1 calc GR . . . .
C55 C 0.5412(2) 0.35035(15) 0.6535(4) 0.0175(15) Uani 1 1 d . . . . .
C56 C 0.5247(2) 0.37942(16) 0.6402(4) 0.0198(15) Uani 1 1 d . . . . .
C57 C 0.4871(2) 0.38280(16) 0.5889(3) 0.0237(16) Uani 1 1 d . . . . .
H57 H 0.475579 0.402467 0.577743 0.028 Uiso 1 1 calc R . . . .
C58 C 0.4661(2) 0.35812(16) 0.5542(4) 0.0207(16) Uani 1 1 d . . . . .
C59 C 0.4830(2) 0.32968(16) 0.5702(3) 0.0204(15) Uani 1 1 d . . . . .
H59 H 0.468275 0.312790 0.546491 0.024 Uiso 1 1 calc R . . . .
C60 C 0.5211(2) 0.32469(16) 0.6200(4) 0.0185(15) Uani 1 1 d . . . . .
C61 C 0.5393(2) 0.29341(16) 0.6362(4) 0.0295(18) Uani 1 1 d . . . . .
H61A H 0.569269 0.291847 0.621885 0.044 Uiso 1 1 calc GR . . . .
H61B H 0.519489 0.278547 0.609554 0.044 Uiso 1 1 calc GR . . . .
H61C H 0.540944 0.289467 0.687682 0.044 Uiso 1 1 calc GR . . . .
C62 C 0.4246(2) 0.36242(18) 0.5010(4) 0.0282(18) Uani 1 1 d . . . . .
H62A H 0.432890 0.369851 0.455623 0.042 Uiso 1 1 calc GR . . . .
H62B H 0.404863 0.377129 0.519944 0.042 Uiso 1 1 calc GR . . . .
H62C H 0.408879 0.343078 0.492981 0.042 Uiso 1 1 calc GR . . . .
C63 C 0.5460(2) 0.40645(16) 0.6822(4) 0.0279(17) Uani 1 1 d . . . . .
H63A H 0.546968 0.402677 0.733700 0.042 Uiso 1 1 calc GR . . . .
H63B H 0.528244 0.424619 0.669019 0.042 Uiso 1 1 calc GR . . . .
H63C H 0.576507 0.409381 0.670959 0.042 Uiso 1 1 calc GR . . . .
I7 I 0.38375(2) 0.45322(2) 0.47928(2) 0.02530(10) Uani 1 1 d . . . . .
I8 I 0.41803(2) 0.45620(2) 0.63256(3) 0.03201(12) Uani 1 1 d . . . . .
Se4 Se 0.33878(3) 0.44685(2) 0.34221(4) 0.02852(19) Uani 1 1 d . . . . .
N7 N 0.41916(18) 0.45502(14) 0.2762(3) 0.0217(13) Uani 1 1 d . . . . .
N8 N 0.35681(19) 0.45293(14) 0.2009(3) 0.0260(14) Uani 1 1 d . . . . .
C64 C 0.3752(2) 0.45201(16) 0.2704(4) 0.0234(16) Uani 1 1 d . . . . .
C65 C 0.3911(2) 0.45599(19) 0.1536(4) 0.0318(19) Uani 1 1 d . . . . .
H65A H 0.385923 0.474164 0.122967 0.038 Uiso 1 1 calc R . . . .
H65B H 0.391988 0.437965 0.122685 0.038 Uiso 1 1 calc R . . . .
C66 C 0.4342(2) 0.45894(18) 0.2059(3) 0.0266(18) Uani 1 1 d . . . . .
H66A H 0.456056 0.443116 0.197209 0.032 Uiso 1 1 calc R . . . .
H66B H 0.448093 0.479036 0.201974 0.032 Uiso 1 1 calc R . . . .
C67 C 0.4522(2) 0.45110(17) 0.3387(4) 0.0194(15) Uani 1 1 d . . . . .
C68 C 0.4657(2) 0.42182(15) 0.3577(4) 0.0181(15) Uani 1 1 d . . . . .
C69 C 0.5007(2) 0.41835(16) 0.4136(4) 0.0223(16) Uani 1 1 d . . . . .
H69 H 0.510212 0.398602 0.428464 0.027 Uiso 1 1 calc R . . . .
C70 C 0.5220(2) 0.44319(17) 0.4481(4) 0.0248(17) Uani 1 1 d . . . . .
C71 C 0.5069(2) 0.47233(18) 0.4268(4) 0.0268(17) Uani 1 1 d . . . . .
H71 H 0.521131 0.489431 0.450289 0.032 Uiso 1 1 calc R . . . .
C72 C 0.4718(2) 0.47659(16) 0.3728(4) 0.0211(16) Uani 1 1 d . . . . .
C73 C 0.4562(3) 0.50776(18) 0.3508(5) 0.039(2) Uani 1 1 d . . . . .
H73A H 0.456996 0.510345 0.299287 0.058 Uiso 1 1 calc GR . . . .
H73B H 0.475877 0.522690 0.377391 0.058 Uiso 1 1 calc GR . . . .
H73C H 0.425510 0.510630 0.361235 0.058 Uiso 1 1 calc GR . . . .
C74 C 0.5608(2) 0.43913(18) 0.5063(4) 0.0319(19) Uani 1 1 d . . . . .
H74A H 0.549689 0.432674 0.550432 0.048 Uiso 1 1 calc GR . . . .
H74B H 0.576825 0.458319 0.514650 0.048 Uiso 1 1 calc GR . . . .
H74C H 0.581091 0.423750 0.491640 0.048 Uiso 1 1 calc GR . . . .
C75 C 0.4445(2) 0.39473(16) 0.3186(4) 0.0302(18) Uani 1 1 d . . . . .
H75A H 0.461609 0.376567 0.334287 0.045 Uiso 1 1 calc GR . . . .
H75B H 0.444293 0.397453 0.266871 0.045 Uiso 1 1 calc GR . . . .
H75C H 0.413674 0.392532 0.329024 0.045 Uiso 1 1 calc GR . . . .
C76 C 0.3100(2) 0.44923(16) 0.1740(4) 0.0253(17) Uani 1 1 d . . . . .
C77 C 0.2957(3) 0.42098(17) 0.1493(4) 0.0292(18) Uani 1 1 d . . . . .
C78 C 0.2520(3) 0.41826(19) 0.1159(5) 0.043(2) Uani 1 1 d . . . . .
H78 H 0.241187 0.398989 0.099441 0.051 Uiso 1 1 calc R . . . .
C79 C 0.2237(3) 0.4431(2) 0.1060(5) 0.050(3) Uani 1 1 d . . . . .
C80 C 0.2395(3) 0.4706(2) 0.1310(5) 0.055(3) Uani 1 1 d . . . . .
H80 H 0.220137 0.487594 0.125113 0.066 Uiso 1 1 calc R . . . .
C81 C 0.2832(3) 0.47451(18) 0.1647(5) 0.037(2) Uani 1 1 d . . . . .
C82 C 0.2997(3) 0.50525(19) 0.1907(6) 0.060(3) Uani 1 1 d . . . . .
H82A H 0.274079 0.518860 0.191288 0.090 Uiso 1 1 calc GR . . . .
H82B H 0.319691 0.513359 0.158520 0.090 Uiso 1 1 calc GR . . . .
H82C H 0.315890 0.503515 0.239246 0.090 Uiso 1 1 calc GR . . . .
C83 C 0.1760(3) 0.4392(2) 0.0674(6) 0.083(4) Uani 1 1 d . . . . .
H83A H 0.175690 0.442630 0.015971 0.125 Uiso 1 1 calc GR . . . .
H83B H 0.156150 0.453847 0.086358 0.125 Uiso 1 1 calc GR . . . .
H83C H 0.165485 0.418683 0.075339 0.125 Uiso 1 1 calc GR . . . .
C84 C 0.3257(3) 0.39330(17) 0.1579(5) 0.042(2) Uani 1 1 d . . . . .
H84A H 0.307555 0.375083 0.147267 0.063 Uiso 1 1 calc GR . . . .
H84B H 0.340870 0.392308 0.207233 0.063 Uiso 1 1 calc GR . . . .
H84C H 0.348027 0.394670 0.124741 0.063 Uiso 1 1 calc GR . . . .
I9 I 0.88234(2) 0.44886(2) 0.98030(2) 0.02403(10) Uani 1 1 d . . . . .
I10 I 0.91776(2) 0.44329(2) 1.13239(3) 0.03026(12) Uani 1 1 d . . . . .
Se5 Se 0.83775(2) 0.45545(2) 0.84334(4) 0.02647(18) Uani 1 1 d . . . . .
N9 N 0.91855(17) 0.45047(13) 0.7768(3) 0.0185(13) Uani 1 1 d . . . . .
N10 N 0.85591(19) 0.44898(14) 0.7033(3) 0.0244(14) Uani 1 1 d . . . . .
C85 C 0.8740(2) 0.45113(16) 0.7716(4) 0.0222(16) Uani 1 1 d . . . . .
C86 C 0.8899(2) 0.44862(19) 0.6542(4) 0.0318(19) Uani 1 1 d . . . . .
H86A H 0.889466 0.467623 0.626428 0.038 Uiso 1 1 calc R . . . .
H86B H 0.885391 0.431335 0.620651 0.038 Uiso 1 1 calc R . . . .
C87 C 0.9338(2) 0.44534(18) 0.7059(4) 0.0264(17) Uani 1 1 d . . . . .
H87A H 0.946811 0.424930 0.702880 0.032 Uiso 1 1 calc R . . . .
H87B H 0.956057 0.460656 0.695990 0.032 Uiso 1 1 calc R . . . .
C88 C 0.9516(2) 0.45352(16) 0.8391(3) 0.0160(14) Uani 1 1 d . . . . .
C89 C 0.9687(2) 0.42791(16) 0.8753(4) 0.0190(15) Uani 1 1 d . . . . .
C90 C 1.0048(2) 0.43169(16) 0.9292(3) 0.0190(15) Uani 1 1 d . . . . .
H90 H 1.017261 0.414459 0.954542 0.023 Uiso 1 1 calc R . . . .
C91 C 1.0231(2) 0.45998(17) 0.9468(3) 0.0206(15) Uani 1 1 d . . . . .
C92 C 1.0043(2) 0.48533(15) 0.9104(3) 0.0177(14) Uani 1 1 d . . . . .
H92 H 1.015938 0.504779 0.923528 0.021 Uiso 1 1 calc R . . . .
C93 C 0.9689(2) 0.48273(16) 0.8552(3) 0.0188(15) Uani 1 1 d . . . . .
C94 C 0.9498(2) 0.50989(16) 0.8132(4) 0.0255(17) Uani 1 1 d . . . . .
H94A H 0.949543 0.506152 0.761863 0.038 Uiso 1 1 calc GR . . . .
H94B H 0.968219 0.527667 0.827410 0.038 Uiso 1 1 calc GR . . . .
H94C H 0.919133 0.513472 0.823107 0.038 Uiso 1 1 calc GR . . . .
C95 C 1.0634(2) 0.46333(16) 1.0025(3) 0.0229(16) Uani 1 1 d . . . . .
H95A H 1.053642 0.467467 1.049116 0.034 Uiso 1 1 calc GR . . . .
H95B H 1.081867 0.480090 0.989360 0.034 Uiso 1 1 calc GR . . . .
H95C H 1.080849 0.444604 1.005291 0.034 Uiso 1 1 calc GR . . . .
C96 C 0.9482(2) 0.39746(16) 0.8584(4) 0.0266(17) Uani 1 1 d . . . . .
H96A H 0.917061 0.397589 0.867778 0.040 Uiso 1 1 calc GR . . . .
H96B H 0.965030 0.382157 0.888590 0.040 Uiso 1 1 calc GR . . . .
H96C H 0.949297 0.392703 0.807848 0.040 Uiso 1 1 calc GR . . . .
C97 C 0.8092(2) 0.45094(18) 0.6755(4) 0.0282(18) Uani 1 1 d . . . . .
C98 C 0.7889(3) 0.47934(19) 0.6673(5) 0.042(2) Uani 1 1 d . . . . .
C99 C 0.7446(3) 0.4802(2) 0.6350(6) 0.058(3) Uani 1 1 d . . . . .
H99 H 0.729944 0.499220 0.628958 0.069 Uiso 1 1 calc R . . . .
C100 C 0.7213(3) 0.4545(2) 0.6116(6) 0.068(4) Uani 1 1 d . . . . .
C101 C 0.7426(3) 0.4272(2) 0.6211(5) 0.046(3) Uani 1 1 d . . . . .
H101 H 0.726239 0.409469 0.606446 0.056 Uiso 1 1 calc R . . . .
C102 C 0.7874(3) 0.42431(18) 0.6516(4) 0.0312(19) Uani 1 1 d . . . . .
C103 C 0.8093(3) 0.39382(17) 0.6593(4) 0.0345(19) Uani 1 1 d . . . . .
H10D H 0.786412 0.378253 0.661451 0.052 Uiso 1 1 calc GR . . . .
H10E H 0.830606 0.393299 0.703396 0.052 Uiso 1 1 calc GR . . . .
H10F H 0.825146 0.390009 0.618038 0.052 Uiso 1 1 calc GR . . . .
C104 C 0.6728(3) 0.4563(3) 0.5776(6) 0.088(4) Uani 1 1 d . U . . .
H10G H 0.669530 0.472099 0.540949 0.132 Uiso 1 1 calc GR . . . .
H10H H 0.653851 0.461003 0.614526 0.132 Uiso 1 1 calc GR . . . .
H10I H 0.663735 0.436795 0.555521 0.132 Uiso 1 1 calc GR . . . .
C105 C 0.8135(3) 0.50801(19) 0.6903(5) 0.054(3) Uani 1 1 d . . . . .
H10J H 0.816539 0.509795 0.742628 0.081 Uiso 1 1 calc GR . . . .
H10K H 0.796748 0.525371 0.668405 0.081 Uiso 1 1 calc GR . . . .
H10L H 0.843282 0.507547 0.674957 0.081 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 I2 2.9106(7) . ?
I1 Se1 2.7486(9) . ?
Se1 C1 1.869(8) . ?
N1 C1 1.337(8) . ?
N1 C3 1.479(9) . ?
N1 C4 1.423(8) . ?
N2 C1 1.320(9) . ?
N2 C2 1.474(8) . ?
N2 C13 1.446(8) . ?
C2 C3 1.533(9) . ?
C4 C5 1.407(10) . ?
C4 C9 1.380(10) . ?
C5 C6 1.387(9) . ?
C5 C12 1.513(10) . ?
C6 C7 1.378(11) . ?
C7 C8 1.369(11) . ?
C7 C11 1.514(10) . ?
C8 C9 1.401(10) . ?
C9 C10 1.526(10) . ?
C13 C14 1.373(9) . ?
C13 C18 1.391(9) . ?
C14 C15 1.402(9) . ?
C14 C21 1.511(9) . ?
C15 C16 1.403(10) . ?
C16 C17 1.384(10) . ?
C16 C20 1.502(9) . ?
C17 C18 1.406(9) . ?
C18 C19 1.500(9) . ?
I3 I4 2.9411(6) . ?
I3 Se2 2.7604(8) . ?
Se2 C22 1.880(6) . ?
N3 C22 1.317(7) . ?
N3 C24 1.471(7) . ?
N3 C25 1.442(7) . ?
N4 C22 1.329(7) . ?
N4 C23 1.480(7) . ?
N4 C34 1.454(7) . ?
C23 C24 1.528(8) . ?
C25 C26 1.387(9) . ?
C25 C30 1.386(9) . ?
C26 C27 1.412(8) . ?
C26 C33 1.500(9) . ?
C27 C28 1.383(9) . ?
C28 C29 1.398(9) . ?
C28 C32 1.509(8) . ?
C29 C30 1.395(8) . ?
C30 C31 1.506(9) . ?
C34 C35 1.406(9) . ?
C34 C39 1.390(10) . ?
C35 C36 1.394(9) . ?
C35 C42 1.504(10) . ?
C36 C37 1.387(11) . ?
C37 C38 1.388(11) . ?
C37 C41 1.520(9) . ?
C38 C39 1.399(9) . ?
C39 C40 1.502(10) . ?
I5 I6 2.9093(7) . ?
I5 Se3 2.7478(9) . ?
Se3 C43 1.873(7) . ?
N5 C43 1.334(8) . ?
N5 C45 1.461(8) . ?
N5 C46 1.439(8) . ?
N6 C43 1.318(9) . ?
N6 C44 1.487(8) . ?
N6 C55 1.440(8) . ?
C44 C45 1.532(9) . ?
C46 C47 1.389(10) . ?
C46 C51 1.383(10) . ?
C47 C48 1.394(9) . ?
C47 C54 1.501(10) . ?
C48 C49 1.384(10) . ?
C49 C50 1.374(10) . ?
C49 C53 1.517(10) . ?
C50 C51 1.397(9) . ?
C51 C52 1.515(10) . ?
C55 C56 1.390(9) . ?
C55 C60 1.397(9) . ?
C56 C57 1.396(9) . ?
C56 C63 1.528(9) . ?
C57 C58 1.382(10) . ?
C58 C59 1.376(9) . ?
C58 C62 1.508(9) . ?
C59 C60 1.399(9) . ?
C60 C61 1.506(9) . ?
I7 I8 2.9353(7) . ?
I7 Se4 2.7642(10) . ?
Se4 C64 1.867(7) . ?
N7 C64 1.324(8) . ?
N7 C66 1.467(8) . ?
N7 C67 1.445(8) . ?
N8 C64 1.351(8) . ?
N8 C65 1.460(9) . ?
N8 C76 1.444(8) . ?
C65 C66 1.528(9) . ?
C67 C68 1.391(9) . ?
C67 C72 1.391(10) . ?
C68 C69 1.397(9) . ?
C68 C75 1.505(9) . ?
C69 C70 1.389(10) . ?
C70 C71 1.408(10) . ?
C70 C74 1.502(9) . ?
C71 C72 1.378(9) . ?
C72 C73 1.498(10) . ?
C76 C77 1.383(10) . ?
C76 C81 1.378(10) . ?
C77 C78 1.386(10) . ?
C77 C84 1.519(10) . ?
C78 C79 1.389(12) . ?
C79 C80 1.368(12) . ?
C79 C83 1.532(10) . ?
C80 C81 1.395(11) . ?
C81 C82 1.507(11) . ?
I9 I10 2.9296(7) . ?
I9 Se5 2.7592(9) . ?
Se5 C85 1.860(7) . ?
N9 C85 1.333(8) . ?
N9 C87 1.487(8) . ?
N9 C88 1.439(8) . ?
N10 C85 1.332(8) . ?
N10 C86 1.469(9) . ?
N10 C97 1.438(8) . ?
C86 C87 1.541(9) . ?
C88 C89 1.386(9) . ?
C88 C93 1.413(9) . ?
C89 C90 1.396(9) . ?
C89 C96 1.498(9) . ?
C90 C91 1.391(10) . ?
C91 C92 1.395(9) . ?
C91 C95 1.500(9) . ?
C92 C93 1.391(9) . ?
C93 C94 1.510(9) . ?
C97 C98 1.398(11) . ?
C97 C102 1.395(10) . ?
C98 C99 1.391(11) . ?
C98 C105 1.505(11) . ?
C99 C100 1.378(12) . ?
C100 C101 1.369(12) . ?
C100 C104 1.517(12) . ?
C101 C102 1.401(10) . ?
C102 C103 1.501(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Se1 I1 I2 169.84(3) . . ?
C1 Se1 I1 115.4(2) . . ?
C1 N1 C3 110.5(6) . . ?
C1 N1 C4 125.2(6) . . ?
C4 N1 C3 124.0(6) . . ?
C1 N2 C2 111.5(6) . . ?
C1 N2 C13 129.0(6) . . ?
C13 N2 C2 119.3(6) . . ?
N1 C1 Se1 118.7(5) . . ?
N2 C1 Se1 129.8(5) . . ?
N2 C1 N1 111.4(7) . . ?
N2 C2 C3 102.5(6) . . ?
N1 C3 C2 102.7(5) . . ?
C5 C4 N1 117.5(6) . . ?
C9 C4 N1 120.4(7) . . ?
C9 C4 C5 122.0(7) . . ?
C4 C5 C12 120.9(7) . . ?
C6 C5 C4 117.7(7) . . ?
C6 C5 C12 121.4(7) . . ?
C7 C6 C5 121.5(7) . . ?
C6 C7 C11 120.1(8) . . ?
C8 C7 C6 119.5(7) . . ?
C8 C7 C11 120.4(7) . . ?
C7 C8 C9 121.7(7) . . ?
C4 C9 C8 117.6(7) . . ?
C4 C9 C10 122.0(7) . . ?
C8 C9 C10 120.3(7) . . ?
C14 C13 N2 118.9(6) . . ?
C14 C13 C18 123.1(6) . . ?
C18 C13 N2 118.0(6) . . ?
C13 C14 C15 118.3(6) . . ?
C13 C14 C21 122.1(6) . . ?
C15 C14 C21 119.6(6) . . ?
C14 C15 C16 121.0(6) . . ?
C15 C16 C20 120.4(7) . . ?
C17 C16 C15 118.3(6) . . ?
C17 C16 C20 121.3(6) . . ?
C16 C17 C18 122.2(7) . . ?
C13 C18 C17 117.0(6) . . ?
C13 C18 C19 121.4(6) . . ?
C17 C18 C19 121.5(6) . . ?
Se2 I3 I4 171.80(2) . . ?
C22 Se2 I3 112.96(18) . . ?
C22 N3 C24 111.3(5) . . ?
C22 N3 C25 130.4(5) . . ?
C25 N3 C24 117.9(4) . . ?
C22 N4 C23 111.5(5) . . ?
C22 N4 C34 126.6(5) . . ?
C34 N4 C23 121.2(5) . . ?
N3 C22 Se2 128.6(4) . . ?
N3 C22 N4 111.3(5) . . ?
N4 C22 Se2 120.1(4) . . ?
N4 C23 C24 102.1(4) . . ?
N3 C24 C23 103.5(5) . . ?
C26 C25 N3 118.2(6) . . ?
C30 C25 N3 118.6(6) . . ?
C30 C25 C26 122.8(5) . . ?
C25 C26 C27 117.6(6) . . ?
C25 C26 C33 121.8(6) . . ?
C27 C26 C33 120.6(6) . . ?
C28 C27 C26 121.3(6) . . ?
C27 C28 C29 118.9(6) . . ?
C27 C28 C32 120.5(6) . . ?
C29 C28 C32 120.6(6) . . ?
C30 C29 C28 121.3(6) . . ?
C25 C30 C29 118.0(6) . . ?
C25 C30 C31 121.0(6) . . ?
C29 C30 C31 121.0(6) . . ?
C35 C34 N4 117.2(6) . . ?
C39 C34 N4 118.8(6) . . ?
C39 C34 C35 123.5(6) . . ?
C34 C35 C42 122.1(6) . . ?
C36 C35 C34 116.6(7) . . ?
C36 C35 C42 121.3(7) . . ?
C37 C36 C35 121.5(7) . . ?
C36 C37 C41 120.0(7) . . ?
C38 C37 C36 120.0(6) . . ?
C38 C37 C41 120.0(7) . . ?
C37 C38 C39 120.9(7) . . ?
C34 C39 C38 117.3(7) . . ?
C34 C39 C40 122.5(6) . . ?
C38 C39 C40 120.3(7) . . ?
Se3 I5 I6 168.69(3) . . ?
C43 Se3 I5 115.6(2) . . ?
C43 N5 C45 111.0(6) . . ?
C43 N5 C46 126.2(6) . . ?
C46 N5 C45 122.6(6) . . ?
C43 N6 C44 110.6(6) . . ?
C43 N6 C55 128.2(6) . . ?
C55 N6 C44 120.7(6) . . ?
N5 C43 Se3 117.9(5) . . ?
N6 C43 Se3 130.3(5) . . ?
N6 C43 N5 111.8(6) . . ?
N6 C44 C45 102.5(5) . . ?
N5 C45 C44 103.0(5) . . ?
C47 C46 N5 118.2(6) . . ?
C51 C46 N5 118.7(6) . . ?
C51 C46 C47 123.0(7) . . ?
C46 C47 C48 116.5(7) . . ?
C46 C47 C54 121.8(7) . . ?
C48 C47 C54 121.7(7) . . ?
C49 C48 C47 122.8(7) . . ?
C48 C49 C53 120.0(7) . . ?
C50 C49 C48 118.1(7) . . ?
C50 C49 C53 121.8(7) . . ?
C49 C50 C51 121.8(7) . . ?
C46 C51 C50 117.7(7) . . ?
C46 C51 C52 122.6(7) . . ?
C50 C51 C52 119.7(7) . . ?
C56 C55 N6 118.6(6) . . ?
C56 C55 C60 123.3(7) . . ?
C60 C55 N6 117.9(6) . . ?
C55 C56 C57 117.5(6) . . ?
C55 C56 C63 121.1(6) . . ?
C57 C56 C63 121.4(6) . . ?
C58 C57 C56 121.3(7) . . ?
C57 C58 C62 120.1(7) . . ?
C59 C58 C57 119.2(7) . . ?
C59 C58 C62 120.7(7) . . ?
C58 C59 C60 122.5(6) . . ?
C55 C60 C59 116.2(6) . . ?
C55 C60 C61 122.2(6) . . ?
C59 C60 C61 121.7(6) . . ?
Se4 I7 I8 170.62(3) . . ?
C64 Se4 I7 113.7(2) . . ?
C64 N7 C66 111.5(5) . . ?
C64 N7 C67 129.0(6) . . ?
C67 N7 C66 119.0(5) . . ?
C64 N8 C65 111.2(6) . . ?
C64 N8 C76 126.2(6) . . ?
C76 N8 C65 122.4(6) . . ?
N7 C64 Se4 129.2(5) . . ?
N7 C64 N8 110.7(6) . . ?
N8 C64 Se4 120.1(5) . . ?
N8 C65 C66 103.0(6) . . ?
N7 C66 C65 103.4(5) . . ?
C68 C67 N7 117.9(6) . . ?
C68 C67 C72 123.0(6) . . ?
C72 C67 N7 118.9(6) . . ?
C67 C68 C69 117.6(6) . . ?
C67 C68 C75 121.7(6) . . ?
C69 C68 C75 120.7(6) . . ?
C70 C69 C68 121.3(7) . . ?
C69 C70 C71 118.8(7) . . ?
C69 C70 C74 120.7(7) . . ?
C71 C70 C74 120.5(7) . . ?
C72 C71 C70 121.5(7) . . ?
C67 C72 C73 121.4(7) . . ?
C71 C72 C67 117.8(7) . . ?
C71 C72 C73 120.8(7) . . ?
C77 C76 N8 117.9(7) . . ?
C81 C76 N8 118.7(7) . . ?
C81 C76 C77 122.7(7) . . ?
C76 C77 C78 117.8(7) . . ?
C76 C77 C84 122.6(7) . . ?
C78 C77 C84 119.7(7) . . ?
C77 C78 C79 121.4(8) . . ?
C78 C79 C83 119.8(9) . . ?
C80 C79 C78 118.6(8) . . ?
C80 C79 C83 121.7(9) . . ?
C79 C80 C81 122.1(8) . . ?
C76 C81 C80 117.3(8) . . ?
C76 C81 C82 122.1(7) . . ?
C80 C81 C82 120.6(8) . . ?
Se5 I9 I10 172.14(3) . . ?
C85 Se5 I9 114.1(2) . . ?
C85 N9 C87 111.5(5) . . ?
C85 N9 C88 129.6(6) . . ?
C88 N9 C87 118.9(5) . . ?
C85 N10 C86 112.2(6) . . ?
C85 N10 C97 127.0(6) . . ?
C97 N10 C86 120.3(6) . . ?
N9 C85 Se5 129.3(5) . . ?
N10 C85 Se5 120.3(5) . . ?
N10 C85 N9 110.4(6) . . ?
N10 C86 C87 102.5(5) . . ?
N9 C87 C86 102.1(5) . . ?
C89 C88 N9 119.7(6) . . ?
C89 C88 C93 122.7(6) . . ?
C93 C88 N9 117.2(6) . . ?
C88 C89 C90 117.5(6) . . ?
C88 C89 C96 121.1(6) . . ?
C90 C89 C96 121.4(6) . . ?
C91 C90 C89 121.8(6) . . ?
C90 C91 C92 119.0(6) . . ?
C90 C91 C95 120.9(6) . . ?
C92 C91 C95 120.1(6) . . ?
C93 C92 C91 121.4(6) . . ?
C88 C93 C94 120.8(6) . . ?
C92 C93 C88 117.5(6) . . ?
C92 C93 C94 121.8(6) . . ?
C98 C97 N10 119.2(7) . . ?
C102 C97 N10 117.5(7) . . ?
C102 C97 C98 123.0(7) . . ?
C97 C98 C105 122.3(8) . . ?
C99 C98 C97 117.0(8) . . ?
C99 C98 C105 120.6(8) . . ?
C100 C99 C98 122.4(8) . . ?
C99 C100 C104 121.0(9) . . ?
C101 C100 C99 118.4(8) . . ?
C101 C100 C104 120.6(9) . . ?
C100 C101 C102 123.0(8) . . ?
C97 C102 C101 116.1(7) . . ?
C97 C102 C103 123.1(7) . . ?
C101 C102 C103 120.7(7) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.123 0.244 0.202 12.7 0.0 ?
2 0.121 0.442 0.198 9.5 0.0 ?
3 0.121 0.558 0.698 9.5 0.0 ?
4 0.123 0.756 0.702 12.7 0.0 ?
5 0.250 0.250 0.500 577.2 99.6 ?
6 0.250 0.750 1.000 577.2 99.6 ?
7 0.246 0.347 -0.003 71.4 0.0 ?
8 0.246 0.653 0.497 71.4 0.0 ?
9 0.254 0.153 0.003 71.4 0.0 ?
10 0.254 0.847 0.503 71.4 0.0 ?
11 0.377 0.256 0.798 12.7 0.9 ?
12 0.377 0.744 0.298 12.7 0.9 ?
13 0.379 0.058 0.802 9.5 0.5 ?
14 0.379 0.942 0.302 9.5 0.5 ?
15 0.621 0.058 0.698 9.5 0.0 ?
16 0.623 0.256 0.702 12.7 0.0 ?
17 0.623 0.744 0.202 12.7 0.0 ?
18 0.621 0.942 0.198 9.5 0.0 ?
19 0.750 0.250 1.000 577.2 99.6 ?
20 0.750 0.750 0.500 577.2 99.6 ?
21 0.746 0.153 0.497 71.4 0.0 ?
22 0.746 0.847 -0.003 71.4 0.0 ?
23 0.754 0.347 0.503 71.4 0.0 ?
24 0.754 0.653 0.003 71.4 0.0 ?
25 0.877 0.244 0.298 12.7 0.9 ?
26 0.877 0.756 0.798 12.7 0.9 ?
27 0.879 0.442 0.302 9.5 0.5 ?
28 0.879 0.558 0.802 9.5 0.5 ?

_olex2_date_sample_data_collection 2020-02-03
_olex2_exptl_crystal_mounting_method 'mounted on a LithoLoop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.893
_oxdiff_exptl_absorpt_empirical_full_min 0.582
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ms256
_database_code_depnum_ccdc_archive 'CCDC 2121858'
loop_
_audit_author_name
_audit_author_address
'Marina Saab'
;Ghent University
Belgium
;
_audit_update_record             
;
2021-11-12 deposited with the CCDC.	2022-02-07 downloaded from the CCDC.
;
_audit_creation_date             2020-09-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H36 I2 N2 Se, C H2 Cl2'
_chemical_formula_sum            'C28 H38 Cl2 I2 N2 Se'
_chemical_formula_weight         806.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C27 H36 I2 N2 Se'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.7433(2)
_cell_length_b                   18.7344(2)
_cell_length_c                   16.2982(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.6540(10)
_cell_angle_gamma                90
_cell_volume                     3200.65(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13747
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      73.5350
_cell_measurement_theta_min      3.6100
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    18.405
_exptl_absorpt_correction_T_max  0.430
_exptl_absorpt_correction_T_min  0.096
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.673
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1576
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-6 7 3 0.0068
-2 -11 -3 0.0869
-1 -3 10 0.0197
-4 10 -1 0.0161
6 5 0 0.0617
6 -5 -3 0.0550
-1 -2 1 0.0558
3 6 -9 0.0443
2 1 -11 0.0669

_exptl_crystal_size_max          0.166
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.078
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-5.6615 6.8765 3.4026 0.0577 0.2447 0.9679
-1.6656 -11.1086 -2.8371 0.1881 0.7835 -0.5922
-0.7989 -3.1117 10.1757 -0.9683 0.2319 0.0924
-3.9037 9.8013 -0.7186 0.4035 -0.0955 0.9100
6.0503 5.4910 0.1166 -0.2290 -0.9572 -0.1769
6.4058 -4.7134 -2.9534 -0.1053 -0.4431 -0.8903
-1.0000 -2.0000 1.0000 -0.0745 0.2145 -0.0156
2.7328 6.1174 -8.8636 0.7929 -0.6076 -0.0463
1.7232 1.0535 -10.5352 0.9267 -0.2222 -0.3030

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0663
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            36795
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.919
_diffrn_reflns_theta_min         3.646
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00  33.00   1.00    2.50    --  -41.68  38.00  60.00   99
  2  ω   -122.00  -1.00   1.00    2.50    --  -41.68 -19.00  90.00  121
  3  ω      6.00  83.00   1.00    2.50    --   41.68 -99.00   0.00   77
  4  ω     23.00 107.00   1.00   15.00    --  106.01 -94.00-180.00   84
  5  ω     33.00 132.00   1.00   15.00    --  106.01 -45.00-120.00   99
  6  ω    103.00 178.00   1.00   15.00    --  106.01  77.00 150.00   75
  7  ω     97.00 178.00   1.00   15.00    --  106.01 125.00-120.00   81
  8  ω     23.00 107.00   1.00   15.00    --  106.01 -94.00  60.00   84
  9  ω    103.00 178.00   1.00   15.00    --  106.01  77.00 -60.00   75
 10  ω     97.00 178.00   1.00   15.00    --  106.01 125.00 120.00   81
 11  ω   -115.00 -14.00   1.00    2.50    --  -41.68 -57.00 -60.00  101
 12  ω   -115.00 -14.00   1.00    2.50    --  -41.68 -56.00  34.00  101
 13  ω     14.00 115.00   1.00    2.50    --   41.68  57.00 -90.00  101
 14  ω     78.00 178.00   1.00   15.00    --  106.01  30.00 120.00  100
 15  ω     78.00 178.00   1.00   15.00    --  106.01  30.00-120.00  100
 16  ω     77.00 178.00   1.00   15.00    --  106.01  61.00 -30.00  101
 17  ω     23.00 107.00   1.00   15.00    --  106.01 -94.00 -90.00   84
 18  ω     77.00 178.00   1.00   15.00    --  106.01  61.00 -90.00  101
 19  ω     80.00 178.00   1.00   15.00    --  106.01  45.00  30.00   98
 20  ω    -87.00  -6.00   1.00    2.50    --  -41.68 125.00 150.00   81
 21  ω     14.00  48.00   1.00    2.50    --   41.68  57.00-180.00   34
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0492818000
_diffrn_orient_matrix_UB_12      0.0146080000
_diffrn_orient_matrix_UB_13      -0.0945641000
_diffrn_orient_matrix_UB_21      -0.1095734000
_diffrn_orient_matrix_UB_22      -0.0535454000
_diffrn_orient_matrix_UB_23      -0.0021855000
_diffrn_orient_matrix_UB_31      -0.0846838000
_diffrn_orient_matrix_UB_32      0.0606516000
_diffrn_orient_matrix_UB_33      0.0209746000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5648
_reflns_number_total             6397
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         2.176
_refine_diff_density_min         -0.788
_refine_diff_density_rms         0.119
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         6397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0350
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0558P)²+1.5037P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0933
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C13(H13), C22(H22), C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7), C8(H8), C18(H18), C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C27(H27A,
 H27B,H27C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.85430(2) 0.34191(2) 0.66832(2) 0.02725(8) Uani 1 1 d . . . . .
I2 I 1.12293(3) 0.39496(2) 0.71152(2) 0.03453(9) Uani 1 1 d . . . . .
Se1 Se 0.60876(4) 0.29777(2) 0.62978(2) 0.02470(10) Uani 1 1 d . . . . .
N1 N 0.6316(3) 0.18190(16) 0.51786(18) 0.0207(6) Uani 1 1 d . . . . .
N2 N 0.5956(3) 0.28236(16) 0.45130(18) 0.0206(6) Uani 1 1 d . . . . .
C1 C 0.6137(3) 0.25227(19) 0.5283(2) 0.0211(6) Uani 1 1 d . . . . .
C2 C 0.6020(4) 0.2306(2) 0.3920(2) 0.0235(7) Uani 1 1 d . . . . .
H2 H 0.592416 0.237683 0.333272 0.028 Uiso 1 1 calc R . . . .
C3 C 0.6246(4) 0.1674(2) 0.4340(2) 0.0229(7) Uani 1 1 d . . . . .
H3 H 0.633706 0.122010 0.410034 0.027 Uiso 1 1 calc R . . . .
C4 C 0.6379(4) 0.12827(19) 0.5830(2) 0.0217(7) Uani 1 1 d . . . . .
C5 C 0.7569(4) 0.10355(19) 0.6263(2) 0.0245(7) Uani 1 1 d . . . . .
C6 C 0.7568(4) 0.0526(2) 0.6892(2) 0.0309(8) Uani 1 1 d . . . . .
H6 H 0.835755 0.034621 0.720430 0.037 Uiso 1 1 calc R . . . .
C7 C 0.6445(5) 0.0280(2) 0.7066(3) 0.0339(9) Uani 1 1 d . . . . .
H7 H 0.647028 -0.006266 0.749959 0.041 Uiso 1 1 calc R . . . .
C8 C 0.5281(4) 0.0527(2) 0.6616(3) 0.0320(8) Uani 1 1 d . . . . .
H8 H 0.451551 0.034968 0.674060 0.038 Uiso 1 1 calc R . . . .
C9 C 0.5218(4) 0.1033(2) 0.5981(2) 0.0253(7) Uani 1 1 d . . . . .
C10 C 0.8814(4) 0.1291(2) 0.6073(2) 0.0279(8) Uani 1 1 d . . . . .
H10 H 0.864254 0.173485 0.572635 0.033 Uiso 1 1 calc R . . . .
C11 C 0.9344(5) 0.0719(3) 0.5560(3) 0.0386(10) Uani 1 1 d . . . . .
H11A H 0.947070 0.027096 0.587699 0.058 Uiso 1 1 calc GR . . . .
H11B H 1.016173 0.088113 0.545268 0.058 Uiso 1 1 calc GR . . . .
H11C H 0.873786 0.064240 0.502304 0.058 Uiso 1 1 calc GR . . . .
C12 C 0.9812(4) 0.1461(3) 0.6874(3) 0.0355(9) Uani 1 1 d . . . . .
H12A H 0.943542 0.177533 0.723441 0.053 Uiso 1 1 calc GR . . . .
H12B H 1.054331 0.169946 0.672446 0.053 Uiso 1 1 calc GR . . . .
H12C H 1.009534 0.101688 0.717505 0.053 Uiso 1 1 calc GR . . . .
C13 C 0.3930(4) 0.1278(2) 0.5466(3) 0.0294(8) Uani 1 1 d . . . . .
H13 H 0.408294 0.161484 0.502212 0.035 Uiso 1 1 calc R . . . .
C14 C 0.3158(5) 0.1670(3) 0.6013(3) 0.0405(10) Uani 1 1 d . . . . .
H14A H 0.236215 0.184851 0.565808 0.061 Uiso 1 1 calc GR . . . .
H14B H 0.365696 0.207195 0.629747 0.061 Uiso 1 1 calc GR . . . .
H14C H 0.296004 0.134039 0.643372 0.061 Uiso 1 1 calc GR . . . .
C15 C 0.3165(5) 0.0637(3) 0.5032(4) 0.0494(12) Uani 1 1 d . . . . .
H15A H 0.365860 0.039241 0.467690 0.074 Uiso 1 1 calc GR . . . .
H15B H 0.235609 0.080490 0.468259 0.074 Uiso 1 1 calc GR . . . .
H15C H 0.299191 0.030578 0.545834 0.074 Uiso 1 1 calc GR . . . .
C16 C 0.5614(4) 0.35634(19) 0.4315(2) 0.0217(7) Uani 1 1 d . . . . .
C17 C 0.6556(4) 0.4030(2) 0.4146(2) 0.0230(7) Uani 1 1 d . . . . .
C18 C 0.6169(4) 0.4728(2) 0.3922(2) 0.0278(8) Uani 1 1 d . . . . .
H18 H 0.677372 0.505710 0.379526 0.033 Uiso 1 1 calc R . . . .
C19 C 0.4940(4) 0.4954(2) 0.3880(2) 0.0276(8) Uani 1 1 d . . . . .
H19 H 0.470846 0.543459 0.373415 0.033 Uiso 1 1 calc R . . . .
C20 C 0.4028(4) 0.4477(2) 0.4052(2) 0.0274(8) Uani 1 1 d . . . . .
H20 H 0.318130 0.463795 0.402418 0.033 Uiso 1 1 calc R . . . .
C21 C 0.4345(4) 0.3767(2) 0.4265(2) 0.0246(7) Uani 1 1 d . . . . .
C22 C 0.3325(4) 0.3248(2) 0.4405(2) 0.0275(8) Uani 1 1 d . . . . .
H22 H 0.377731 0.283263 0.472404 0.033 Uiso 1 1 calc R . . . .
C23 C 0.2587(7) 0.2965(4) 0.3578(4) 0.074(2) Uani 1 1 d . . . . .
H23A H 0.215425 0.336040 0.323745 0.111 Uiso 1 1 calc GR . . . .
H23B H 0.195249 0.261896 0.367834 0.111 Uiso 1 1 calc GR . . . .
H23C H 0.317334 0.273099 0.327929 0.111 Uiso 1 1 calc GR . . . .
C24 C 0.2459(6) 0.3551(3) 0.4925(5) 0.0630(18) Uani 1 1 d . . . . .
H24A H 0.297105 0.373206 0.545684 0.094 Uiso 1 1 calc GR . . . .
H24B H 0.188335 0.317681 0.504016 0.094 Uiso 1 1 calc GR . . . .
H24C H 0.195774 0.394189 0.461681 0.094 Uiso 1 1 calc GR . . . .
C25 C 0.7923(4) 0.3803(2) 0.4193(2) 0.0270(8) Uani 1 1 d . . . . .
H25 H 0.807441 0.334115 0.450629 0.032 Uiso 1 1 calc R . . . .
C26 C 0.8877(4) 0.4354(2) 0.4655(3) 0.0335(9) Uani 1 1 d . . . . .
H26A H 0.888618 0.476999 0.429144 0.050 Uiso 1 1 calc GR . . . .
H26B H 0.973074 0.414146 0.479692 0.050 Uiso 1 1 calc GR . . . .
H26C H 0.862458 0.450318 0.517114 0.050 Uiso 1 1 calc GR . . . .
C27 C 0.8142(4) 0.3683(3) 0.3299(3) 0.0333(9) Uani 1 1 d . . . . .
H27A H 0.761924 0.328160 0.303652 0.050 Uiso 1 1 calc GR . . . .
H27B H 0.904472 0.357750 0.333136 0.050 Uiso 1 1 calc GR . . . .
H27C H 0.790144 0.411514 0.296248 0.050 Uiso 1 1 calc GR . . . .
Cl1 Cl 1.0377(2) 0.11319(7) 0.30126(9) 0.0679(5) Uani 1 1 d . . . . .
Cl2 Cl 0.96736(12) 0.21062(7) 0.42171(7) 0.0456(3) Uani 1 1 d . . . . .
C28 C 0.9501(5) 0.1896(3) 0.3141(3) 0.0456(11) Uani 1 1 d . . . . .
H28A H 0.858815 0.181427 0.288422 0.055 Uiso 1 1 calc R . . . .
H28B H 0.979886 0.230273 0.284748 0.055 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 I2 2.9870(4) . ?
I1 Se1 2.7039(5) . ?
Se1 C1 1.872(3) . ?
N1 C1 1.348(5) . ?
N1 C3 1.379(4) . ?
N1 C4 1.453(4) . ?
N2 C1 1.350(5) . ?
N2 C2 1.381(5) . ?
N2 C16 1.452(5) . ?
C2 C3 1.362(5) . ?
C4 C5 1.397(5) . ?
C4 C9 1.403(5) . ?
C5 C6 1.401(5) . ?
C5 C10 1.515(6) . ?
C6 C7 1.378(6) . ?
C7 C8 1.384(6) . ?
C8 C9 1.393(5) . ?
C9 C13 1.524(6) . ?
C10 C11 1.542(6) . ?
C10 C12 1.530(6) . ?
C13 C14 1.531(6) . ?
C13 C15 1.538(6) . ?
C16 C17 1.409(5) . ?
C16 C21 1.401(6) . ?
C17 C18 1.397(5) . ?
C17 C25 1.515(6) . ?
C18 C19 1.374(6) . ?
C19 C20 1.399(6) . ?
C20 C21 1.397(6) . ?
C21 C22 1.520(5) . ?
C22 C23 1.503(7) . ?
C22 C24 1.500(6) . ?
C25 C26 1.531(6) . ?
C25 C27 1.541(5) . ?
Cl1 C28 1.750(6) . ?
Cl2 C28 1.767(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Se1 I1 I2 178.343(13) . . ?
C1 Se1 I1 97.43(11) . . ?
C1 N1 C3 109.8(3) . . ?
C1 N1 C4 124.7(3) . . ?
C3 N1 C4 124.9(3) . . ?
C1 N2 C2 109.7(3) . . ?
C1 N2 C16 125.7(3) . . ?
C2 N2 C16 124.3(3) . . ?
N1 C1 Se1 126.1(3) . . ?
N1 C1 N2 106.7(3) . . ?
N2 C1 Se1 127.2(3) . . ?
C3 C2 N2 106.9(3) . . ?
C2 C3 N1 107.0(3) . . ?
C5 C4 N1 119.3(3) . . ?
C5 C4 C9 123.5(3) . . ?
C9 C4 N1 117.3(3) . . ?
C4 C5 C6 116.6(4) . . ?
C4 C5 C10 123.0(3) . . ?
C6 C5 C10 120.4(4) . . ?
C7 C6 C5 121.3(4) . . ?
C6 C7 C8 120.6(4) . . ?
C7 C8 C9 120.9(4) . . ?
C4 C9 C13 122.5(3) . . ?
C8 C9 C4 117.2(4) . . ?
C8 C9 C13 120.3(4) . . ?
C5 C10 C11 109.8(3) . . ?
C5 C10 C12 112.1(3) . . ?
C12 C10 C11 109.5(4) . . ?
C9 C13 C14 111.5(3) . . ?
C9 C13 C15 110.3(4) . . ?
C14 C13 C15 109.8(4) . . ?
C17 C16 N2 118.6(3) . . ?
C21 C16 N2 117.9(3) . . ?
C21 C16 C17 123.4(3) . . ?
C16 C17 C25 123.1(3) . . ?
C18 C17 C16 116.5(4) . . ?
C18 C17 C25 120.4(3) . . ?
C19 C18 C17 121.9(4) . . ?
C18 C19 C20 120.1(4) . . ?
C21 C20 C19 121.0(4) . . ?
C16 C21 C22 122.8(3) . . ?
C20 C21 C16 117.1(3) . . ?
C20 C21 C22 120.1(4) . . ?
C23 C22 C21 110.3(3) . . ?
C24 C22 C21 113.6(4) . . ?
C24 C22 C23 111.7(5) . . ?
C17 C25 C26 111.9(3) . . ?
C17 C25 C27 109.9(3) . . ?
C26 C25 C27 109.8(3) . . ?
Cl1 C28 Cl2 111.0(3) . . ?

_olex2_date_sample_data_collection 2019-11-18
_olex2_exptl_crystal_mounting_method 'mounted on a nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 2.320
_oxdiff_exptl_absorpt_empirical_full_min 0.505
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ms342
_database_code_depnum_ccdc_archive 'CCDC 2121857'
loop_
_audit_author_name
_audit_author_address
'Marina Saab'
;Ghent University
Belgium
;
_audit_update_record             
;
2021-11-12 deposited with the CCDC.	2022-02-07 downloaded from the CCDC.
;
_audit_creation_date             2020-12-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H26 Cl N2, H O4 S'
_chemical_formula_sum            'C21 H27 Cl N2 O4 S'
_chemical_formula_weight         438.95
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H24 N2 S Cl2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.7200(7)
_cell_length_b                   13.2714(8)
_cell_length_c                   15.9571(8)
_cell_angle_alpha                78.387(5)
_cell_angle_beta                 74.490(5)
_cell_angle_gamma                66.020(6)
_cell_volume                     2173.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4124
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      73.3160
_cell_measurement_theta_min      4.2020
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.702
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.825
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             928
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 -7 -8 0.0155
2 6 -6 0.0682
3 7 8 0.0378
0 -2 9 0.0476
-8 -5 -4 0.0292
-1 7 4 0.0374
7 6 5 0.0259
1 -7 -4 0.0177

_exptl_crystal_size_max          0.128
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.054
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-3.3993 -6.8939 -7.7520 0.0749 0.3161 0.9458
1.8551 6.1237 -5.5854 0.2066 0.8609 -0.4649
3.4175 6.9636 7.6575 -0.0719 -0.3035 -0.9501
0.0423 -2.1235 9.2798 -0.2324 -0.9708 -0.0597
-7.5147 -4.5466 -3.5945 0.7704 -0.1838 0.6105
-1.1346 6.8523 3.7085 0.5898 -0.1420 -0.7950
6.8352 6.3582 4.5229 -0.5611 0.1335 -0.8169
0.5828 -7.1634 -3.9596 -0.5318 0.1282 0.8371

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1000
_diffrn_reflns_av_unetI/netI     0.1002
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            32389
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.832
_diffrn_reflns_theta_min         2.890
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00  34.00   1.00    1.00    --  -41.68  77.00   0.00  108
  2  ω    -66.00  33.00   1.00    1.00    --  -41.68  38.00 -90.00   99
  3  ω   -116.00 -17.00   1.00    1.00    --  -41.68 -38.00  90.00   99
  4  ω      8.00  42.00   1.00    1.00    --   41.68  81.00  73.38   34
  5  ω      7.00  34.00   1.00    1.00    --   41.68  83.00-122.17   27
  6  ω     81.00 178.00   1.00    3.70    --  106.01  40.00  48.75   97
  7  ω     33.00 132.00   1.00    3.70    --  106.01 -45.00-180.00   99
  8  ω     34.00 135.00   1.00    3.70    --  106.01 -61.00  90.00  101
  9  ω     26.00 108.00   1.00    3.70    --  106.01-102.00-147.00   82
 10  ω     33.00 132.00   1.00    3.70    --  106.01 -45.00 -30.00   99
 11  ω     97.00 178.00   1.00    3.70    --  106.01 125.00 -90.00   81
 12  ω     33.00 112.00   1.00    3.70    --  106.01-125.00  30.00   79
 13  ω     33.00 112.00   1.00    3.70    --  106.01-125.00  90.00   79
 14  ω     23.00 107.00   1.00    3.70    --  106.01 -94.00  90.00   84
 15  ω     23.00 107.00   1.00    3.70    --  106.01 -94.00 -60.00   84
 16  ω     18.00 178.00   1.00    3.70    --  106.01   0.00  30.00  160
 17  ω    -87.00  -6.00   1.00    1.00    --  -41.68 125.00  60.00   81
 18  ω     10.00  36.00   1.00    1.00    --   41.68  75.00-168.86   26
 19  ω      8.00  42.00   1.00    1.00    --   41.68  81.00 -31.90   34
 20  ω     17.00 116.00   1.00    1.00    --   41.68  38.00 -60.00   99
 21  ω      8.00  42.00   1.00    1.00    --   41.68  81.00  43.15   34
 22  ω     77.00 178.00   1.00    3.70    --  106.01  61.00  90.00  101
 23  ω     53.00 178.00   1.00    3.70    --  106.01  15.00-150.00  125
 24  ω     77.00 178.00   1.00    3.70    --  106.01  61.00 -10.35  101
 25  ω     77.00 178.00   1.00    3.70    --  106.01  61.00 -60.00  101
 26  ω     77.00 178.00   1.00    3.70    --  106.01  62.00-167.04  101
 27  ω     77.00 178.00   1.00    3.70    --  106.01  61.00-120.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1392908000
_diffrn_orient_matrix_UB_12      0.0678165000
_diffrn_orient_matrix_UB_13      -0.0088912000
_diffrn_orient_matrix_UB_21      0.0467911000
_diffrn_orient_matrix_UB_22      0.0389302000
_diffrn_orient_matrix_UB_23      -0.0959178000
_diffrn_orient_matrix_UB_31      -0.0059976000
_diffrn_orient_matrix_UB_32      -0.1010308000
_diffrn_orient_matrix_UB_33      -0.0295245000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5776
_reflns_number_total             8649
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     537
_refine_ls_number_reflns         8649
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0912
_refine_ls_R_factor_gt           0.0514
_refine_ls_restrained_S_all      0.992
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0169P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1141
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C23(H23A,H23B), C24(H24A,H24B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C15(H15), C17(H17), C27(H27), C29(H29), C36(H36), C38(H38)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C19(H19A,H19B,
 H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C31(H31A,H31B,H31C), C32(H32A,
 H32B,H32C), C33(H33A,H33B,H33C), C40(H40A,H40B,H40C), C41(H41A,H41B,H41C),
 C42(H42A,H42B,H42C)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4), O8(H8A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.49343(7) 0.90359(6) 0.61781(5) 0.02400(15) Uani 1 1 d . . . . .
N1 N 0.6035(2) 1.0119(2) 0.66877(16) 0.0219(5) Uani 1 1 d . . . . .
N2 N 0.3923(2) 1.0818(2) 0.70227(17) 0.0242(5) Uani 1 1 d . . . . .
C1 C 0.4957(3) 1.0052(2) 0.66578(18) 0.0202(6) Uani 1 1 d . . . . .
C2 C 0.4289(3) 1.1612(3) 0.7335(2) 0.0267(6) Uani 1 1 d . . . . .
H2A H 0.389350 1.170983 0.795970 0.032 Uiso 1 1 calc R . . . .
H2B H 0.403545 1.234434 0.698536 0.032 Uiso 1 1 calc R . . . .
C3 C 0.5748(3) 1.1043(3) 0.7199(2) 0.0255(6) Uani 1 1 d . . . . .
H3A H 0.617081 1.155720 0.686836 0.031 Uiso 1 1 calc R . . . .
H3B H 0.602150 1.076097 0.776498 0.031 Uiso 1 1 calc R . . . .
C4 C 0.7312(3) 0.9313(2) 0.64766(19) 0.0212(6) Uani 1 1 d . . . . .
C5 C 0.7716(3) 0.8400(3) 0.7099(2) 0.0256(6) Uani 1 1 d . . . . .
C6 C 0.8981(3) 0.7677(3) 0.6916(2) 0.0303(7) Uani 1 1 d . . . . .
H6 H 0.927979 0.705769 0.732787 0.036 Uiso 1 1 calc R . . . .
C7 C 0.9824(3) 0.7830(3) 0.6150(2) 0.0295(7) Uani 1 1 d . . . . .
C8 C 0.9374(3) 0.8749(3) 0.5547(2) 0.0269(6) Uani 1 1 d . . . . .
H8 H 0.994054 0.885693 0.501797 0.032 Uiso 1 1 calc R . . . .
C9 C 0.8123(3) 0.9504(3) 0.57016(19) 0.0233(6) Uani 1 1 d . . . . .
C10 C 0.7663(3) 1.0490(3) 0.5047(2) 0.0306(7) Uani 1 1 d . . . . .
H10A H 0.693290 1.047527 0.486869 0.046 Uiso 1 1 calc GR . . . .
H10B H 0.835371 1.046083 0.453379 0.046 Uiso 1 1 calc GR . . . .
H10C H 0.740412 1.117418 0.531375 0.046 Uiso 1 1 calc GR . . . .
C11 C 1.1180(3) 0.7003(3) 0.5956(3) 0.0410(9) Uani 1 1 d . . . . .
H11A H 1.121253 0.641288 0.565678 0.062 Uiso 1 1 calc GR . . . .
H11B H 1.147554 0.668217 0.650477 0.062 Uiso 1 1 calc GR . . . .
H11C H 1.173237 0.737870 0.558028 0.062 Uiso 1 1 calc GR . . . .
C12 C 0.6815(3) 0.8206(3) 0.7923(2) 0.0350(8) Uani 1 1 d . . . . .
H12A H 0.648046 0.884238 0.826175 0.053 Uiso 1 1 calc GR . . . .
H12B H 0.727075 0.753443 0.827202 0.053 Uiso 1 1 calc GR . . . .
H12C H 0.610704 0.811296 0.777492 0.053 Uiso 1 1 calc GR . . . .
C13 C 0.2626(3) 1.0895(2) 0.71649(19) 0.0217(6) Uani 1 1 d . . . . .
C14 C 0.1877(3) 1.1523(3) 0.65508(19) 0.0248(6) Uani 1 1 d . . . . .
C15 C 0.0641(3) 1.1565(3) 0.6713(2) 0.0285(7) Uani 1 1 d . . . . .
H15 H 0.012682 1.197885 0.629748 0.034 Uiso 1 1 calc R . . . .
C16 C 0.0122(3) 1.1023(3) 0.7460(2) 0.0282(7) Uani 1 1 d . . . . .
C17 C 0.0872(3) 1.0451(3) 0.8076(2) 0.0281(7) Uani 1 1 d . . . . .
H17 H 0.051567 1.010837 0.860350 0.034 Uiso 1 1 calc R . . . .
C18 C 0.2130(3) 1.0367(3) 0.7941(2) 0.0247(6) Uani 1 1 d . . . . .
C19 C 0.2937(4) 0.9712(3) 0.8604(2) 0.0354(8) Uani 1 1 d . . . . .
H19A H 0.325792 1.018952 0.878956 0.053 Uiso 1 1 calc GR . . . .
H19B H 0.365793 0.908478 0.834276 0.053 Uiso 1 1 calc GR . . . .
H19C H 0.241909 0.943363 0.911290 0.053 Uiso 1 1 calc GR . . . .
C20 C -0.1200(3) 1.1025(3) 0.7591(3) 0.0404(9) Uani 1 1 d . . . . .
H20A H -0.115033 1.037602 0.735812 0.061 Uiso 1 1 calc GR . . . .
H20B H -0.172471 1.170231 0.728436 0.061 Uiso 1 1 calc GR . . . .
H20C H -0.158669 1.099844 0.821729 0.061 Uiso 1 1 calc GR . . . .
C21 C 0.2388(3) 1.2133(3) 0.5733(2) 0.0337(7) Uani 1 1 d . . . . .
H21A H 0.224848 1.192897 0.522194 0.051 Uiso 1 1 calc GR . . . .
H21B H 0.330387 1.193412 0.568128 0.051 Uiso 1 1 calc GR . . . .
H21C H 0.194281 1.293437 0.576212 0.051 Uiso 1 1 calc GR . . . .
Cl2 Cl 0.48990(7) 0.37543(6) 0.11354(5) 0.02690(16) Uani 1 1 d . . . . .
N3 N 0.5927(2) 0.4705(2) 0.18646(16) 0.0226(5) Uani 1 1 d . . . . .
N4 N 0.3827(2) 0.5288(2) 0.22336(16) 0.0235(5) Uani 1 1 d . . . . .
C22 C 0.4882(3) 0.4636(3) 0.17778(18) 0.0223(6) Uani 1 1 d . . . . .
C23 C 0.4146(3) 0.5906(3) 0.27615(19) 0.0244(6) Uani 1 1 d . . . . .
H23A H 0.387580 0.571242 0.339546 0.029 Uiso 1 1 calc R . . . .
H23B H 0.373451 0.671741 0.262090 0.029 Uiso 1 1 calc R . . . .
C24 C 0.5601(3) 0.5522(3) 0.2489(2) 0.0249(6) Uani 1 1 d . . . . .
H24A H 0.586741 0.614920 0.220188 0.030 Uiso 1 1 calc R . . . .
H24B H 0.600840 0.517056 0.299824 0.030 Uiso 1 1 calc R . . . .
C25 C 0.7223(3) 0.4027(3) 0.15170(19) 0.0220(6) Uani 1 1 d . . . . .
C26 C 0.7757(3) 0.2955(3) 0.1926(2) 0.0257(6) Uani 1 1 d . . . . .
C27 C 0.9025(3) 0.2336(3) 0.1602(2) 0.0283(7) Uani 1 1 d . . . . .
H27 H 0.940356 0.160939 0.187474 0.034 Uiso 1 1 calc R . . . .
C28 C 0.9765(3) 0.2743(3) 0.0887(2) 0.0282(7) Uani 1 1 d . . . . .
C29 C 0.9201(3) 0.3819(3) 0.0509(2) 0.0256(6) Uani 1 1 d . . . . .
H29 H 0.970170 0.411255 0.003196 0.031 Uiso 1 1 calc R . . . .
C30 C 0.7938(3) 0.4477(2) 0.08025(19) 0.0220(6) Uani 1 1 d . . . . .
C31 C 0.7353(3) 0.5628(3) 0.0368(2) 0.0286(7) Uani 1 1 d . . . . .
H31A H 0.746529 0.615942 0.065443 0.043 Uiso 1 1 calc GR . . . .
H31B H 0.644057 0.581085 0.041870 0.043 Uiso 1 1 calc GR . . . .
H31C H 0.777287 0.566323 -0.025068 0.043 Uiso 1 1 calc GR . . . .
C32 C 1.1120(3) 0.2029(3) 0.0530(3) 0.0406(9) Uani 1 1 d . . . . .
H32A H 1.114696 0.168708 0.003142 0.061 Uiso 1 1 calc GR . . . .
H32B H 1.145622 0.144850 0.098628 0.061 Uiso 1 1 calc GR . . . .
H32C H 1.164041 0.248654 0.033892 0.061 Uiso 1 1 calc GR . . . .
C33 C 0.6978(3) 0.2474(3) 0.2682(2) 0.0323(7) Uani 1 1 d . . . . .
H33A H 0.652871 0.300383 0.312060 0.049 Uiso 1 1 calc GR . . . .
H33B H 0.754360 0.178123 0.294611 0.049 Uiso 1 1 calc GR . . . .
H33C H 0.635445 0.232505 0.247232 0.049 Uiso 1 1 calc GR . . . .
C34 C 0.2538(3) 0.5421(3) 0.22650(19) 0.0225(6) Uani 1 1 d . . . . .
C35 C 0.1901(3) 0.6169(3) 0.16292(19) 0.0237(6) Uani 1 1 d . . . . .
C36 C 0.0635(3) 0.6323(3) 0.1704(2) 0.0273(7) Uani 1 1 d . . . . .
H36 H 0.018046 0.682938 0.128475 0.033 Uiso 1 1 calc R . . . .
C37 C 0.0008(3) 0.5762(3) 0.2373(2) 0.0271(6) Uani 1 1 d . . . . .
C38 C 0.0677(3) 0.5045(3) 0.2998(2) 0.0279(7) Uani 1 1 d . . . . .
H38 H 0.025172 0.467311 0.346703 0.034 Uiso 1 1 calc R . . . .
C39 C 0.1946(3) 0.4856(3) 0.2957(2) 0.0265(6) Uani 1 1 d . . . . .
C40 C 0.2650(4) 0.4053(3) 0.3631(2) 0.0392(8) Uani 1 1 d . . . . .
H40A H 0.355124 0.369380 0.335885 0.059 Uiso 1 1 calc GR . . . .
H40B H 0.227483 0.348977 0.386724 0.059 Uiso 1 1 calc GR . . . .
H40C H 0.258203 0.445499 0.410627 0.059 Uiso 1 1 calc GR . . . .
C41 C -0.1340(3) 0.5903(3) 0.2415(2) 0.0354(8) Uani 1 1 d . . . . .
H41A H -0.175274 0.659396 0.206787 0.053 Uiso 1 1 calc GR . . . .
H41B H -0.180793 0.593042 0.302424 0.053 Uiso 1 1 calc GR . . . .
H41C H -0.134073 0.527531 0.217990 0.053 Uiso 1 1 calc GR . . . .
C42 C 0.2557(4) 0.6762(3) 0.0885(2) 0.0362(8) Uani 1 1 d . . . . .
H42A H 0.307001 0.703818 0.110418 0.054 Uiso 1 1 calc GR . . . .
H42B H 0.191702 0.738764 0.061451 0.054 Uiso 1 1 calc GR . . . .
H42C H 0.311420 0.624902 0.044883 0.054 Uiso 1 1 calc GR . . . .
S1 S 0.48756(7) 0.65597(6) 0.49283(5) 0.02376(16) Uani 1 1 d . . . . .
O1 O 0.5074(2) 0.7419(2) 0.52196(16) 0.0326(5) Uani 1 1 d . . . . .
O2 O 0.4258(2) 0.59529(19) 0.56459(15) 0.0328(5) Uani 1 1 d . . . . .
O3 O 0.4241(3) 0.6905(2) 0.42089(17) 0.0478(7) Uani 1 1 d . . . . .
O4 O 0.6254(2) 0.5698(2) 0.46141(19) 0.0392(6) Uani 1 1 d . . . . .
H4 H 0.620474 0.512484 0.450581 0.059 Uiso 1 1 calc GR . . . .
S2 S 0.51343(7) 0.15553(6) -0.05043(4) 0.02048(15) Uani 1 1 d . . . . .
O5 O 0.5059(2) 0.19812(19) 0.02757(14) 0.0314(5) Uani 1 1 d . . . . .
O6 O 0.4065(2) 0.12203(18) -0.04499(14) 0.0277(5) Uani 1 1 d . . . . .
O7 O 0.5338(2) 0.22673(17) -0.12994(13) 0.0247(4) Uani 1 1 d . . . . .
O8 O 0.6368(2) 0.04577(18) -0.06244(14) 0.0254(5) Uani 1 1 d . . . . .
H8A H 0.623744 -0.005940 -0.026341 0.038 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.692(3) . ?
N1 C1 1.316(4) . ?
N1 C3 1.485(4) . ?
N1 C4 1.439(4) . ?
N2 C1 1.304(4) . ?
N2 C2 1.496(4) . ?
N2 C13 1.439(4) . ?
C2 C3 1.536(4) . ?
C4 C5 1.407(4) . ?
C4 C9 1.392(4) . ?
C5 C6 1.389(5) . ?
C5 C12 1.501(5) . ?
C6 C7 1.389(5) . ?
C7 C8 1.403(5) . ?
C7 C11 1.511(5) . ?
C8 C9 1.388(5) . ?
C9 C10 1.507(4) . ?
C13 C14 1.401(4) . ?
C13 C18 1.400(5) . ?
C14 C15 1.382(5) . ?
C14 C21 1.506(5) . ?
C15 C16 1.390(5) . ?
C16 C17 1.390(5) . ?
C16 C20 1.506(5) . ?
C17 C18 1.393(5) . ?
C18 C19 1.506(4) . ?
Cl2 C22 1.695(3) . ?
N3 C22 1.310(4) . ?
N3 C24 1.486(4) . ?
N3 C25 1.437(4) . ?
N4 C22 1.307(4) . ?
N4 C23 1.490(4) . ?
N4 C34 1.436(4) . ?
C23 C24 1.531(4) . ?
C25 C26 1.400(4) . ?
C25 C30 1.407(4) . ?
C26 C27 1.385(5) . ?
C26 C33 1.508(4) . ?
C27 C28 1.396(5) . ?
C28 C29 1.393(5) . ?
C28 C32 1.501(5) . ?
C29 C30 1.384(4) . ?
C30 C31 1.503(4) . ?
C34 C35 1.404(4) . ?
C34 C39 1.394(5) . ?
C35 C36 1.387(5) . ?
C35 C42 1.500(5) . ?
C36 C37 1.392(5) . ?
C37 C38 1.395(5) . ?
C37 C41 1.499(5) . ?
C38 C39 1.390(5) . ?
C39 C40 1.508(4) . ?
S1 O1 1.434(2) . ?
S1 O2 1.464(2) . ?
S1 O3 1.432(2) . ?
S1 O4 1.570(3) . ?
S2 O5 1.435(2) . ?
S2 O6 1.468(2) . ?
S2 O7 1.449(2) . ?
S2 O8 1.582(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C3 109.0(2) . . ?
C1 N1 C4 128.3(3) . . ?
C4 N1 C3 121.0(2) . . ?
C1 N2 C2 108.9(3) . . ?
C1 N2 C13 127.7(3) . . ?
C13 N2 C2 123.3(2) . . ?
N1 C1 Cl1 121.7(2) . . ?
N2 C1 Cl1 123.0(2) . . ?
N2 C1 N1 115.3(3) . . ?
N2 C2 C3 102.8(2) . . ?
N1 C3 C2 102.9(2) . . ?
C5 C4 N1 118.0(3) . . ?
C9 C4 N1 119.2(3) . . ?
C9 C4 C5 122.7(3) . . ?
C4 C5 C12 121.5(3) . . ?
C6 C5 C4 117.2(3) . . ?
C6 C5 C12 121.2(3) . . ?
C7 C6 C5 122.2(3) . . ?
C6 C7 C8 118.4(3) . . ?
C6 C7 C11 120.7(3) . . ?
C8 C7 C11 120.8(3) . . ?
C9 C8 C7 121.8(3) . . ?
C4 C9 C10 121.4(3) . . ?
C8 C9 C4 117.7(3) . . ?
C8 C9 C10 120.9(3) . . ?
C14 C13 N2 120.0(3) . . ?
C18 C13 N2 118.3(3) . . ?
C18 C13 C14 121.6(3) . . ?
C13 C14 C21 121.9(3) . . ?
C15 C14 C13 117.9(3) . . ?
C15 C14 C21 120.2(3) . . ?
C14 C15 C16 122.5(3) . . ?
C15 C16 C20 121.2(3) . . ?
C17 C16 C15 118.1(3) . . ?
C17 C16 C20 120.7(3) . . ?
C16 C17 C18 121.9(3) . . ?
C13 C18 C19 121.1(3) . . ?
C17 C18 C13 118.0(3) . . ?
C17 C18 C19 120.9(3) . . ?
C22 N3 C24 109.7(3) . . ?
C22 N3 C25 127.6(3) . . ?
C25 N3 C24 122.3(2) . . ?
C22 N4 C23 109.2(3) . . ?
C22 N4 C34 128.2(3) . . ?
C34 N4 C23 122.6(2) . . ?
N3 C22 Cl2 122.6(2) . . ?
N4 C22 Cl2 122.6(2) . . ?
N4 C22 N3 114.8(3) . . ?
N4 C23 C24 103.3(2) . . ?
N3 C24 C23 102.8(2) . . ?
C26 C25 N3 119.0(3) . . ?
C26 C25 C30 121.9(3) . . ?
C30 C25 N3 119.0(3) . . ?
C25 C26 C33 121.5(3) . . ?
C27 C26 C25 117.9(3) . . ?
C27 C26 C33 120.6(3) . . ?
C26 C27 C28 122.2(3) . . ?
C27 C28 C32 120.7(3) . . ?
C29 C28 C27 118.0(3) . . ?
C29 C28 C32 121.3(3) . . ?
C30 C29 C28 122.4(3) . . ?
C25 C30 C31 121.4(3) . . ?
C29 C30 C25 117.6(3) . . ?
C29 C30 C31 121.0(3) . . ?
C35 C34 N4 118.6(3) . . ?
C39 C34 N4 118.6(3) . . ?
C39 C34 C35 122.7(3) . . ?
C34 C35 C42 121.9(3) . . ?
C36 C35 C34 117.2(3) . . ?
C36 C35 C42 120.9(3) . . ?
C35 C36 C37 122.3(3) . . ?
C36 C37 C38 118.2(3) . . ?
C36 C37 C41 121.2(3) . . ?
C38 C37 C41 120.5(3) . . ?
C39 C38 C37 122.0(3) . . ?
C34 C39 C40 121.8(3) . . ?
C38 C39 C34 117.5(3) . . ?
C38 C39 C40 120.6(3) . . ?
O1 S1 O2 112.32(14) . . ?
O1 S1 O4 104.76(14) . . ?
O2 S1 O4 105.28(15) . . ?
O3 S1 O1 115.07(15) . . ?
O3 S1 O2 110.95(18) . . ?
O3 S1 O4 107.67(17) . . ?
O5 S2 O6 113.04(14) . . ?
O5 S2 O7 113.92(13) . . ?
O5 S2 O8 108.12(13) . . ?
O6 S2 O8 105.28(13) . . ?
O7 S2 O6 111.92(13) . . ?
O7 S2 O8 103.66(12) . . ?

