# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_s3707ma
_database_code_depnum_ccdc_archive 'CCDC 1445149'
_audit_update_record             
;
2017-03-14 deposited with the CCDC.
2017-03-14 downloaded from the CCDC.
;
_audit_creation_date             2017-03-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C11 H14 Br N S3'
_chemical_formula_sum            'C11 H14 Br N S3'
_chemical_formula_weight         336.32
_chemical_melting_point          ?
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'
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'
Br Br -0.6763 1.2805 '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           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'
'x-1/2, y-1/2, -z-1/2'

_cell_length_a                   13.0722(6)
_cell_length_b                   7.8927(4)
_cell_length_c                   25.4406(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2624.8(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9716
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      72.26
_cell_measurement_theta_min      4.85
_shelx_estimated_absorpt_T_max   0.343
_shelx_estimated_absorpt_T_min   0.268
_exptl_absorpt_coefficient_mu    8.498
_exptl_absorpt_correction_T_max  0.3434
_exptl_absorpt_correction_T_min  0.206104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.702
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0710
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            15381
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.292
_diffrn_reflns_theta_min         3.474
_diffrn_ambient_temperature      180.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2428
_reflns_number_total             2584
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.656
_refine_diff_density_min         -0.919
_refine_diff_density_rms         0.108
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2584
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0378
_refine_ls_restrained_S_all      1.062
_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)+(0.0418P)²+3.5874P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.0960
_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 Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C11(H11)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.64181(3) 0.16693(4) 0.27541(2) 0.03686(14) Uani 1 1 d . . . . .
C1 C 0.63779(18) 0.3005(3) 0.21370(10) 0.0203(5) Uani 1 1 d . . . . .
C2 C 0.61528(19) 0.4716(3) 0.21639(9) 0.0197(5) Uani 1 1 d . . . . .
H2 H 0.6033 0.5261 0.2491 0.024 Uiso 1 1 calc R . . . .
C3 C 0.61094(19) 0.5605(3) 0.16928(10) 0.0188(5) Uani 1 1 d . . . . .
C4 C 0.5836(2) 0.7454(3) 0.16880(10) 0.0248(5) Uani 1 1 d . . . . .
H4A H 0.6164 0.7998 0.1380 0.030 Uiso 1 1 calc R . . . .
H4B H 0.6115 0.7995 0.2009 0.030 Uiso 1 1 calc R . . . .
C5 C 0.4124(2) 0.6824(3) 0.10380(11) 0.0280(6) Uani 1 1 d . . . . .
H5A H 0.3717 0.7621 0.0823 0.034 Uiso 1 1 calc R . . . .
H5B H 0.4758 0.6552 0.0842 0.034 Uiso 1 1 calc R . . . .
C6 C 0.3517(2) 0.5219(4) 0.11245(12) 0.0325(6) Uani 1 1 d . . . . .
H6A H 0.2884 0.5498 0.1319 0.039 Uiso 1 1 calc R . . . .
H6B H 0.3924 0.4434 0.1345 0.039 Uiso 1 1 calc R . . . .
C7 C 0.4385(2) 0.3175(3) 0.03422(10) 0.0232(5) Uani 1 1 d . . . . .
H7A H 0.4358 0.2821 -0.0031 0.028 Uiso 1 1 calc R . . . .
H7B H 0.4938 0.4024 0.0377 0.028 Uiso 1 1 calc R . . . .
C8 C 0.4645(2) 0.1648(3) 0.06775(10) 0.0230(5) Uani 1 1 d . . . . .
H8A H 0.4109 0.0775 0.0631 0.028 Uiso 1 1 calc R . . . .
H8B H 0.4647 0.1988 0.1052 0.028 Uiso 1 1 calc R . . . .
C9 C 0.67423(19) 0.2476(3) 0.06782(9) 0.0208(5) Uani 1 1 d . . . . .
H9A H 0.7456 0.2055 0.0671 0.025 Uiso 1 1 calc R . . . .
H9B H 0.6680 0.3372 0.0408 0.025 Uiso 1 1 calc R . . . .
C10 C 0.65247(17) 0.3233(3) 0.12113(10) 0.0174(5) Uani 1 1 d . . . . .
C11 C 0.65560(18) 0.2228(3) 0.16591(10) 0.0197(5) Uani 1 1 d . . . . .
H11 H 0.6695 0.1048 0.1638 0.024 Uiso 1 1 calc R . . . .
N1 N 0.62993(15) 0.4894(3) 0.12223(8) 0.0173(4) Uani 1 1 d . . . . .
S1 S 0.44597(5) 0.78360(8) 0.16602(3) 0.02894(18) Uani 1 1 d . . . . .
S2 S 0.31793(5) 0.41597(9) 0.05157(3) 0.03211(18) Uani 1 1 d . . . . .
S3 S 0.58804(5) 0.07388(7) 0.05131(2) 0.02568(17) 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 C1 1.891(3) . ?
C1 C2 1.384(4) . ?
C1 C11 1.381(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.390(3) . ?
C3 C4 1.502(3) . ?
C3 N1 1.345(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 S1 1.825(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.511(4) . ?
C5 S1 1.826(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 S2 1.815(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.515(3) . ?
C7 S2 1.812(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 S3 1.816(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.509(3) . ?
C9 S3 1.823(3) . ?
C10 C11 1.389(4) . ?
C10 N1 1.344(3) . ?
C11 H11 0.9500 . ?

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
C2 C1 Br1 120.6(2) . . ?
C11 C1 Br1 118.6(2) . . ?
C11 C1 C2 120.8(2) . . ?
C1 C2 H2 121.3 . . ?
C1 C2 C3 117.3(2) . . ?
C3 C2 H2 121.3 . . ?
C2 C3 C4 120.5(2) . . ?
N1 C3 C2 123.3(2) . . ?
N1 C3 C4 116.2(2) . . ?
C3 C4 H4A 108.9 . . ?
C3 C4 H4B 108.9 . . ?
C3 C4 S1 113.28(18) . . ?
H4A C4 H4B 107.7 . . ?
S1 C4 H4A 108.9 . . ?
S1 C4 H4B 108.9 . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
C6 C5 S1 111.5(2) . . ?
S1 C5 H5A 109.3 . . ?
S1 C5 H5B 109.3 . . ?
C5 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
C5 C6 S2 112.9(2) . . ?
H6A C6 H6B 107.8 . . ?
S2 C6 H6A 109.0 . . ?
S2 C6 H6B 109.0 . . ?
H7A C7 H7B 107.7 . . ?
C8 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
C8 C7 S2 113.54(18) . . ?
S2 C7 H7A 108.9 . . ?
S2 C7 H7B 108.9 . . ?
C7 C8 H8A 109.1 . . ?
C7 C8 H8B 109.1 . . ?
C7 C8 S3 112.60(18) . . ?
H8A C8 H8B 107.8 . . ?
S3 C8 H8A 109.1 . . ?
S3 C8 H8B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C10 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C10 C9 S3 112.85(17) . . ?
S3 C9 H9A 109.0 . . ?
S3 C9 H9B 109.0 . . ?
C11 C10 C9 120.3(2) . . ?
N1 C10 C9 116.5(2) . . ?
N1 C10 C11 123.1(2) . . ?
C1 C11 C10 117.6(2) . . ?
C1 C11 H11 121.2 . . ?
C10 C11 H11 121.2 . . ?
C10 N1 C3 117.8(2) . . ?
C4 S1 C5 101.41(12) . . ?
C7 S2 C6 101.16(13) . . ?
C8 S3 C9 101.49(11) . . ?

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 C1 C2 C3 -178.27(18) . . . . ?
Br1 C1 C11 C10 -179.88(17) . . . . ?
C1 C2 C3 C4 178.0(2) . . . . ?
C1 C2 C3 N1 -1.7(4) . . . . ?
C2 C1 C11 C10 1.5(4) . . . . ?
C2 C3 C4 S1 -86.9(3) . . . . ?
C2 C3 N1 C10 1.2(3) . . . . ?
C3 C4 S1 C5 -60.8(2) . . . . ?
C4 C3 N1 C10 -178.6(2) . . . . ?
C5 C6 S2 C7 76.7(2) . . . . ?
C6 C5 S1 C4 109.3(2) . . . . ?
C7 C8 S3 C9 63.3(2) . . . . ?
C8 C7 S2 C6 74.1(2) . . . . ?
C9 C10 C11 C1 178.2(2) . . . . ?
C9 C10 N1 C3 -179.5(2) . . . . ?
C10 C9 S3 C8 47.6(2) . . . . ?
C11 C1 C2 C3 0.3(4) . . . . ?
C11 C10 N1 C3 0.9(3) . . . . ?
N1 C3 C4 S1 92.9(2) . . . . ?
N1 C10 C11 C1 -2.2(4) . . . . ?
S1 C5 C6 S2 -179.41(14) . . . . ?
S2 C7 C8 S3 -177.65(13) . . . . ?
S3 C9 C10 C11 58.2(3) . . . . ?
S3 C9 C10 N1 -121.4(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_s4010ma
_database_code_depnum_ccdc_archive 'CCDC 1445157'
_audit_update_record             
;
2017-03-14 deposited with the CCDC.
2017-03-14 downloaded from the CCDC.
;
_audit_creation_date             2017-03-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C24 H25 N3 O S3'
_chemical_formula_sum            'C24 H25 N3 O S3'
_chemical_formula_weight         467.65
_chemical_melting_point          ?
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'
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                   5.5032(2)
_cell_length_b                   13.7541(5)
_cell_length_c                   16.2814(5)
_cell_angle_alpha                66.950(2)
_cell_angle_beta                 85.649(2)
_cell_angle_gamma                82.232(2)
_cell_volume                     1123.22(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8486
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.91
_cell_measurement_theta_min      3.52
_shelx_estimated_absorpt_T_max   0.883
_shelx_estimated_absorpt_T_min   0.646
_exptl_absorpt_coefficient_mu    3.189
_exptl_absorpt_correction_T_max  0.8831
_exptl_absorpt_correction_T_min  0.761229
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            gold
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            20554
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.258
_diffrn_reflns_theta_min         3.515
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3755
_reflns_number_total             4168
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.604
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0394
_refine_ls_restrained_S_all      1.046
_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)+(0.0596P)²+0.6536P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1021
_refine_ls_wR_factor_ref         0.1073
_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:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11), C13(H13), C14(H14), C16(H16), C17(H17), C19(H19), C20(H20),
 C22(H22), C23(H23)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
C1 C 0.2668(4) 0.37204(16) 0.41205(13) 0.0331(4) Uani 1 1 d . . . . .
H1A H 0.0977 0.4014 0.3916 0.040 Uiso 1 1 calc R . . . .
H1B H 0.2613 0.3391 0.4781 0.040 Uiso 1 1 calc R . . . .
C2 C 0.4288(4) 0.46089(17) 0.38144(12) 0.0318(4) Uani 1 1 d . . . . .
H2A H 0.4443 0.4890 0.3155 0.038 Uiso 1 1 calc R . . . .
H2B H 0.5946 0.4311 0.4053 0.038 Uiso 1 1 calc R . . . .
C3 C 0.0355(4) 0.62371(18) 0.35467(13) 0.0340(4) Uani 1 1 d . . . . .
H3A H -0.0918 0.5761 0.3849 0.041 Uiso 1 1 calc R . . . .
H3B H -0.0210 0.6940 0.3571 0.041 Uiso 1 1 calc R . . . .
C4 C 0.0599(3) 0.63615(16) 0.25803(12) 0.0291(4) Uani 1 1 d . . . . .
C5 C -0.0574(3) 0.58723(16) 0.14915(12) 0.0288(4) Uani 1 1 d . . . . .
C6 C -0.2153(4) 0.52258(17) 0.12361(13) 0.0347(4) Uani 1 1 d . . . . .
H6A H -0.2787 0.5659 0.0632 0.042 Uiso 1 1 calc R . . . .
H6B H -0.3581 0.5076 0.1656 0.042 Uiso 1 1 calc R . . . .
C7 C 0.0267(4) 0.32615(18) 0.23896(14) 0.0370(5) Uani 1 1 d . . . . .
H7A H -0.0865 0.3528 0.2777 0.044 Uiso 1 1 calc R . . . .
H7B H 0.0117 0.2496 0.2569 0.044 Uiso 1 1 calc R . . . .
C8 C 0.2870(4) 0.33956(17) 0.25256(13) 0.0333(4) Uani 1 1 d . . . . .
H8A H 0.3019 0.4164 0.2331 0.040 Uiso 1 1 calc R . . . .
H8B H 0.3995 0.3119 0.2142 0.040 Uiso 1 1 calc R . . . .
C9 C 0.2236(4) 0.70030(16) 0.19962(12) 0.0313(4) Uani 1 1 d . . . . .
H9 H 0.3184 0.7391 0.2198 0.038 Uiso 1 1 calc R . . . .
C10 C 0.2499(3) 0.70818(15) 0.11162(12) 0.0277(4) Uani 1 1 d . . . . .
C11 C 0.1023(3) 0.65000(16) 0.08690(12) 0.0299(4) Uani 1 1 d . . . . .
H11 H 0.1108 0.6532 0.0274 0.036 Uiso 1 1 calc R . . . .
C12 C 0.4284(3) 0.77443(15) 0.04734(12) 0.0278(4) Uani 1 1 d . . . . .
C13 C 0.4793(4) 0.76865(18) -0.03599(13) 0.0358(5) Uani 1 1 d . . . . .
H13 H 0.3941 0.7239 -0.0528 0.043 Uiso 1 1 calc R . . . .
C14 C 0.6506(4) 0.82649(18) -0.09444(13) 0.0357(5) Uani 1 1 d . . . . .
H14 H 0.6837 0.8208 -0.1506 0.043 Uiso 1 1 calc R . . . .
C15 C 0.7748(4) 0.89310(16) -0.07126(13) 0.0310(4) Uani 1 1 d . . . . .
C16 C 0.7249(4) 0.90146(18) 0.01044(14) 0.0403(5) Uani 1 1 d . . . . .
H16 H 0.8074 0.9477 0.0263 0.048 Uiso 1 1 calc R . . . .
C17 C 0.5537(4) 0.84183(18) 0.06926(14) 0.0388(5) Uani 1 1 d . . . . .
H17 H 0.5217 0.8473 0.1255 0.047 Uiso 1 1 calc R . . . .
C18 C 1.2053(4) 0.99145(16) -0.24898(13) 0.0321(4) Uani 1 1 d . . . . .
C19 C 1.3432(4) 0.94836(18) -0.30383(15) 0.0400(5) Uani 1 1 d . . . . .
H19 H 1.3162 0.8803 -0.3009 0.048 Uiso 1 1 calc R . . . .
C20 C 1.5209(4) 1.00295(19) -0.36325(15) 0.0422(5) Uani 1 1 d . . . . .
H20 H 1.6173 0.9720 -0.3996 0.051 Uiso 1 1 calc R . . . .
C21 C 1.5545(4) 1.10317(18) -0.36824(14) 0.0391(5) Uani 1 1 d . . . . .
C22 C 1.4132(4) 1.14775(18) -0.31430(14) 0.0395(5) Uani 1 1 d . . . . .
H22 H 1.4355 1.2169 -0.3187 0.047 Uiso 1 1 calc R . . . .
C23 C 1.2411(4) 1.09207(17) -0.25456(13) 0.0358(4) Uani 1 1 d . . . . .
H23 H 1.1471 1.1224 -0.2173 0.043 Uiso 1 1 calc R . . . .
C24 C 1.8789(5) 1.1218(2) -0.47656(18) 0.0586(7) Uani 1 1 d . . . . .
H24A H 1.9702 1.0554 -0.4376 0.088 Uiso 1 1 calc GR . . . .
H24B H 1.9943 1.1724 -0.5108 0.088 Uiso 1 1 calc GR . . . .
H24C H 1.7821 1.1073 -0.5177 0.088 Uiso 1 1 calc GR . . . .
N1 N -0.0803(3) 0.57940(13) 0.23389(10) 0.0297(3) Uani 1 1 d . . . . .
N2 N 0.9515(3) 0.95718(14) -0.12846(11) 0.0336(4) Uani 1 1 d . . . . .
N3 N 1.0340(3) 0.92718(14) -0.18965(11) 0.0340(4) Uani 1 1 d . . . . .
O1 O 1.7196(3) 1.16570(15) -0.42379(12) 0.0539(4) Uani 1 1 d . . . . .
S1 S 0.31877(9) 0.57008(4) 0.41529(3) 0.03355(14) Uani 1 1 d . . . . .
S2 S 0.38242(10) 0.27156(4) 0.36783(3) 0.03614(14) Uani 1 1 d . . . . .
S3 S -0.06151(10) 0.39735(4) 0.12342(3) 0.03911(15) 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
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.512(3) . ?
C1 S2 1.818(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 S1 1.810(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.512(3) . ?
C3 S1 1.817(2) . ?
C4 C9 1.387(3) . ?
C4 N1 1.344(3) . ?
C5 C6 1.507(3) . ?
C5 C11 1.389(3) . ?
C5 N1 1.339(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 S3 1.815(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.512(3) . ?
C7 S3 1.817(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 S2 1.821(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.392(3) . ?
C10 C11 1.393(3) . ?
C10 C12 1.493(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.395(3) . ?
C12 C17 1.390(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.379(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.388(3) . ?
C15 C16 1.383(3) . ?
C15 N2 1.429(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.391(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.384(3) . ?
C18 C23 1.391(3) . ?
C18 N3 1.422(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.394(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.385(3) . ?
C21 C22 1.393(3) . ?
C21 O1 1.364(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.379(3) . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C24 O1 1.421(3) . ?
N2 N3 1.254(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
H1A C1 H1B 108.1 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 S2 110.70(14) . . ?
S2 C1 H1A 109.5 . . ?
S2 C1 H1B 109.5 . . ?
C1 C2 H2A 108.6 . . ?
C1 C2 H2B 108.6 . . ?
C1 C2 S1 114.45(14) . . ?
H2A C2 H2B 107.6 . . ?
S1 C2 H2A 108.6 . . ?
S1 C2 H2B 108.6 . . ?
H3A C3 H3B 107.7 . . ?
C4 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
C4 C3 S1 113.66(14) . . ?
S1 C3 H3A 108.8 . . ?
S1 C3 H3B 108.8 . . ?
C9 C4 C3 121.02(17) . . ?
N1 C4 C3 116.02(16) . . ?
N1 C4 C9 122.94(17) . . ?
C11 C5 C6 120.58(17) . . ?
N1 C5 C6 116.18(16) . . ?
N1 C5 C11 123.24(17) . . ?
C5 C6 H6A 108.5 . . ?
C5 C6 H6B 108.5 . . ?
C5 C6 S3 114.93(14) . . ?
H6A C6 H6B 107.5 . . ?
S3 C6 H6A 108.5 . . ?
S3 C6 H6B 108.5 . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C8 C7 S3 111.74(14) . . ?
S3 C7 H7A 109.3 . . ?
S3 C7 H7B 109.3 . . ?
C7 C8 H8A 108.9 . . ?
C7 C8 H8B 108.9 . . ?
C7 C8 S2 113.42(14) . . ?
H8A C8 H8B 107.7 . . ?
S2 C8 H8A 108.9 . . ?
S2 C8 H8B 108.9 . . ?
C4 C9 H9 119.8 . . ?
C4 C9 C10 120.36(18) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 C11 116.35(17) . . ?
C9 C10 C12 121.92(17) . . ?
C11 C10 C12 121.73(16) . . ?
C5 C11 C10 120.08(17) . . ?
C5 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C13 C12 C10 120.96(17) . . ?
C17 C12 C10 121.24(17) . . ?
C17 C12 C13 117.79(18) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 C12 121.38(18) . . ?
C14 C13 H13 119.3 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.03(18) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 N2 123.61(18) . . ?
C16 C15 C14 119.71(18) . . ?
C16 C15 N2 116.67(18) . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.74(19) . . ?
C17 C16 H16 120.1 . . ?
C12 C17 C16 121.34(18) . . ?
C12 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C19 C18 C23 119.40(19) . . ?
C19 C18 N3 116.08(18) . . ?
C23 C18 N3 124.53(18) . . ?
C18 C19 H19 119.4 . . ?
C18 C19 C20 121.2(2) . . ?
C20 C19 H19 119.4 . . ?
C19 C20 H20 120.6 . . ?
C21 C20 C19 118.8(2) . . ?
C21 C20 H20 120.6 . . ?
C20 C21 C22 120.25(19) . . ?
O1 C21 C20 125.0(2) . . ?
O1 C21 C22 114.8(2) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 C21 120.4(2) . . ?
C23 C22 H22 119.8 . . ?
C18 C23 H23 120.0 . . ?
C22 C23 C18 119.9(2) . . ?
C22 C23 H23 120.0 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O1 C24 H24A 109.5 . . ?
O1 C24 H24B 109.5 . . ?
O1 C24 H24C 109.5 . . ?
C5 N1 C4 117.04(16) . . ?
N3 N2 C15 113.24(17) . . ?
N2 N3 C18 114.32(17) . . ?
C21 O1 C24 117.2(2) . . ?
C2 S1 C3 102.10(9) . . ?
C1 S2 C8 100.32(10) . . ?
C6 S3 C7 102.62(10) . . ?

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
C1 C2 S1 C3 -65.15(16) . . . . ?
C2 C1 S2 C8 -75.76(16) . . . . ?
C3 C4 C9 C10 177.86(19) . . . . ?
C3 C4 N1 C5 -178.45(17) . . . . ?
C4 C3 S1 C2 -45.48(17) . . . . ?
C4 C9 C10 C11 0.8(3) . . . . ?
C4 C9 C10 C12 -178.57(18) . . . . ?
C5 C6 S3 C7 61.30(16) . . . . ?
C6 C5 C11 C10 -179.06(18) . . . . ?
C6 C5 N1 C4 179.72(17) . . . . ?
C7 C8 S2 C1 -85.34(17) . . . . ?
C8 C7 S3 C6 -95.16(17) . . . . ?
C9 C4 N1 C5 -0.3(3) . . . . ?
C9 C10 C11 C5 -0.9(3) . . . . ?
C9 C10 C12 C13 170.1(2) . . . . ?
C9 C10 C12 C17 -8.3(3) . . . . ?
C10 C12 C13 C14 -177.52(19) . . . . ?
C10 C12 C17 C16 178.2(2) . . . . ?
C11 C5 C6 S3 80.9(2) . . . . ?
C11 C5 N1 C4 0.2(3) . . . . ?
C11 C10 C12 C13 -9.3(3) . . . . ?
C11 C10 C12 C17 172.3(2) . . . . ?
C12 C10 C11 C5 178.44(18) . . . . ?
C12 C13 C14 C15 -0.7(3) . . . . ?
C13 C12 C17 C16 -0.2(3) . . . . ?
C13 C14 C15 C16 -0.3(3) . . . . ?
C13 C14 C15 N2 -178.8(2) . . . . ?
C14 C15 C16 C17 1.0(3) . . . . ?
C14 C15 N2 N3 -18.6(3) . . . . ?
C15 C16 C17 C12 -0.7(4) . . . . ?
C15 N2 N3 C18 178.35(16) . . . . ?
C16 C15 N2 N3 162.9(2) . . . . ?
C17 C12 C13 C14 0.9(3) . . . . ?
C18 C19 C20 C21 -1.5(3) . . . . ?
C19 C18 C23 C22 -0.1(3) . . . . ?
C19 C18 N3 N2 165.31(19) . . . . ?
C19 C20 C21 C22 0.3(3) . . . . ?
C19 C20 C21 O1 -179.4(2) . . . . ?
C20 C21 C22 C23 0.9(3) . . . . ?
C20 C21 O1 C24 -3.9(3) . . . . ?
C21 C22 C23 C18 -1.0(3) . . . . ?
C22 C21 O1 C24 176.4(2) . . . . ?
C23 C18 C19 C20 1.4(3) . . . . ?
C23 C18 N3 N2 -14.5(3) . . . . ?
N1 C4 C9 C10 -0.2(3) . . . . ?
N1 C5 C6 S3 -98.68(18) . . . . ?
N1 C5 C11 C10 0.5(3) . . . . ?
N2 C15 C16 C17 179.6(2) . . . . ?
N3 C18 C19 C20 -178.5(2) . . . . ?
N3 C18 C23 C22 179.7(2) . . . . ?
O1 C21 C22 C23 -179.4(2) . . . . ?
S1 C3 C4 C9 -59.5(2) . . . . ?
S1 C3 C4 N1 118.67(17) . . . . ?
S2 C1 C2 S1 175.94(10) . . . . ?
S3 C7 C8 S2 178.96(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_s4114ma
_database_code_depnum_ccdc_archive 'CCDC 1445158'
_audit_update_record             
;
2017-03-14 deposited with the CCDC.
2017-03-14 downloaded from the CCDC.
;
_audit_creation_date             2017-03-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C11 H16 Br Cu N2 O4 S3, N O3'
_chemical_formula_sum            'C11 H16 Br Cu N3 O7 S3'
_chemical_formula_weight         541.90
_chemical_melting_point          ?
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'
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'
Cu Cu -1.9646 0.5888 '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'
O O 0.0492 0.0322 '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                   7.7435(2)
_cell_length_b                   19.9374(4)
_cell_length_c                   11.9344(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.8650(10)
_cell_angle_gamma                90
_cell_volume                     1809.47(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2907
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.00
_cell_measurement_theta_min      4.38
_shelx_estimated_absorpt_T_max   0.858
_shelx_estimated_absorpt_T_min   0.426
_exptl_absorpt_coefficient_mu    7.920
_exptl_absorpt_correction_T_max  0.8577
_exptl_absorpt_correction_T_min  0.616611
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.989
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1084
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6852
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.994
_diffrn_reflns_theta_min         4.376
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2926
_reflns_number_total             3416
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         1.799
_refine_diff_density_min         -0.544
_refine_diff_density_rms         0.108
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3416
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0367
_refine_ls_restrained_S_all      1.047
_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)+(0.0576P)²+1.5897P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.0979
_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 O(H,H) groups
2. Restrained distances
 O1-H1A = O1-H1B
 0.87 with sigma of 0.02
 H1A-H1B
 1.38 with sigma of 0.04
 Cu1-H1A \\sim Cu1-H1B
 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C11(H11)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 0.71498(5) 0.59351(2) 1.10837(3) 0.02689(13) Uani 1 1 d . . . . .
C1 C 0.5312(4) 0.58687(17) 0.9813(3) 0.0197(7) Uani 1 1 d . . . . .
C2 C 0.3673(5) 0.61363(17) 0.9862(3) 0.0203(7) Uani 1 1 d . . . . .
H2 H 0.3434 0.6319 1.0552 0.024 Uiso 1 1 calc R . . . .
C3 C 0.2395(4) 0.61293(17) 0.8878(3) 0.0182(6) Uani 1 1 d . . . . .
C4 C 0.0580(4) 0.64088(18) 0.8900(3) 0.0211(7) Uani 1 1 d . . . . .
H4A H 0.0703 0.6801 0.9417 0.025 Uiso 1 1 calc R . . . .
H4B H -0.0108 0.6064 0.9221 0.025 Uiso 1 1 calc R . . . .
C5 C 0.0200(4) 0.75121(17) 0.7400(3) 0.0224(7) Uani 1 1 d . . . . .
H5A H -0.0537 0.7731 0.6732 0.027 Uiso 1 1 calc R . . . .
H5B H 0.0054 0.7769 0.8086 0.027 Uiso 1 1 calc R . . . .
C6 C 0.2103(4) 0.75603(17) 0.7272(3) 0.0198(7) Uani 1 1 d . . . . .
H6A H 0.2861 0.7320 0.7906 0.024 Uiso 1 1 calc R . . . .
H6B H 0.2474 0.8036 0.7298 0.024 Uiso 1 1 calc R . . . .
C7 C 0.4581(4) 0.68807(18) 0.6146(3) 0.0196(7) Uani 1 1 d . . . . .
H7A H 0.5387 0.7241 0.5995 0.024 Uiso 1 1 calc R . . . .
H7B H 0.4950 0.6731 0.6946 0.024 Uiso 1 1 calc R . . . .
C8 C 0.4639(4) 0.62919(19) 0.5329(3) 0.0224(7) Uani 1 1 d . . . . .
H8A H 0.5876 0.6143 0.5411 0.027 Uiso 1 1 calc R . . . .
H8B H 0.4267 0.6458 0.4539 0.027 Uiso 1 1 calc R . . . .
C9 C 0.4516(4) 0.52125(19) 0.6821(3) 0.0218(7) Uani 1 1 d . . . . .
H9A H 0.4153 0.4739 0.6874 0.026 Uiso 1 1 calc R . . . .
H9B H 0.5783 0.5214 0.6786 0.026 Uiso 1 1 calc R . . . .
C10 C 0.4268(4) 0.55717(17) 0.7879(3) 0.0183(6) Uani 1 1 d . . . . .
C11 C 0.5613(4) 0.55628(18) 0.8829(3) 0.0204(7) Uani 1 1 d . . . . .
H11 H 0.6707 0.5353 0.8803 0.024 Uiso 1 1 calc R . . . .
Cu1 Cu 0.09954(6) 0.59899(2) 0.64479(4) 0.01402(13) Uani 1 1 d D . . . .
N1 N 0.2703(3) 0.58697(14) 0.7890(2) 0.0155(5) Uani 1 1 d . . . . .
N2 N -0.0676(4) 0.46773(16) 0.7135(3) 0.0216(6) Uani 1 1 d . . . . .
N3 N 0.6820(4) 0.73248(15) 0.3967(3) 0.0200(6) Uani 1 1 d . . . . .
O1 O -0.0865(3) 0.60175(12) 0.5122(2) 0.0179(5) Uani 1 1 d D . . . .
H1A H -0.110(5) 0.6421(11) 0.489(3) 0.027 Uiso 1 1 d DR . . . .
H1B H -0.061(5) 0.5790(19) 0.457(2) 0.027 Uiso 1 1 d DR . . . .
O2 O 0.0409(3) 0.48429(12) 0.6504(2) 0.0211(5) Uani 1 1 d . . . . .
O3 O -0.1117(3) 0.51048(15) 0.7774(3) 0.0333(6) Uani 1 1 d . . . . .
O4 O -0.1247(4) 0.40990(15) 0.7080(3) 0.0353(7) Uani 1 1 d . . . . .
O5 O 0.8221(3) 0.72685(13) 0.4725(2) 0.0241(5) Uani 1 1 d . . . . .
O6 O 0.6467(3) 0.68847(15) 0.3228(2) 0.0291(6) Uani 1 1 d . . . . .
O7 O 0.5859(3) 0.78137(15) 0.3996(2) 0.0308(6) Uani 1 1 d . . . . .
S1 S -0.06326(10) 0.66605(4) 0.75233(7) 0.01887(18) Uani 1 1 d . . . . .
S2 S 0.23369(10) 0.71892(4) 0.59125(7) 0.01829(18) Uani 1 1 d . . . . .
S3 S 0.33038(9) 0.55668(4) 0.55125(7) 0.01623(17) 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 C1 1.879(3) . ?
C1 C2 1.388(5) . ?
C1 C11 1.382(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.386(5) . ?
C3 C4 1.516(5) . ?
C3 N1 1.350(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 S1 1.803(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.513(4) . ?
C5 S1 1.832(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 S2 1.823(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.532(5) . ?
C7 S2 1.815(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 S3 1.815(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.495(5) . ?
C9 S3 1.807(3) . ?
C10 C11 1.388(5) . ?
C10 N1 1.352(4) . ?
C11 H11 0.9500 . ?
Cu1 N1 1.978(3) . ?
Cu1 O1 1.929(2) . ?
Cu1 O2 2.335(3) . ?
Cu1 S1 2.3736(9) . ?
Cu1 S2 2.7304(10) . ?
Cu1 S3 2.4301(8) . ?
N2 O2 1.273(4) . ?
N2 O3 1.234(4) . ?
N2 O4 1.232(4) . ?
N3 O5 1.280(4) . ?
N3 O6 1.237(4) . ?
N3 O7 1.231(4) . ?
O1 H1A 0.859(18) . ?
O1 H1B 0.854(18) . ?

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
C2 C1 Br1 119.9(3) . . ?
C11 C1 Br1 119.6(3) . . ?
C11 C1 C2 120.5(3) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 C1 118.2(3) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 C4 119.9(3) . . ?
N1 C3 C2 121.9(3) . . ?
N1 C3 C4 118.2(3) . . ?
C3 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
C3 C4 S1 114.3(2) . . ?
H4A C4 H4B 107.6 . . ?
S1 C4 H4A 108.7 . . ?
S1 C4 H4B 108.7 . . ?
H5A C5 H5B 107.5 . . ?
C6 C5 H5A 108.4 . . ?
C6 C5 H5B 108.4 . . ?
C6 C5 S1 115.5(2) . . ?
S1 C5 H5A 108.4 . . ?
S1 C5 H5B 108.4 . . ?
C5 C6 H6A 109.9 . . ?
C5 C6 H6B 109.9 . . ?
C5 C6 S2 109.0(2) . . ?
H6A C6 H6B 108.3 . . ?
S2 C6 H6A 109.9 . . ?
S2 C6 H6B 109.9 . . ?
H7A C7 H7B 108.5 . . ?
C8 C7 H7A 110.2 . . ?
C8 C7 H7B 110.2 . . ?
C8 C7 S2 107.7(2) . . ?
S2 C7 H7A 110.2 . . ?
S2 C7 H7B 110.2 . . ?
C7 C8 H8A 108.1 . . ?
C7 C8 H8B 108.1 . . ?
C7 C8 S3 116.6(2) . . ?
H8A C8 H8B 107.3 . . ?
S3 C8 H8A 108.1 . . ?
S3 C8 H8B 108.1 . . ?
H9A C9 H9B 107.6 . . ?
C10 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
C10 C9 S3 114.5(2) . . ?
S3 C9 H9A 108.6 . . ?
S3 C9 H9B 108.6 . . ?
C11 C10 C9 119.2(3) . . ?
N1 C10 C9 118.5(3) . . ?
N1 C10 C11 122.2(3) . . ?
C1 C11 C10 117.9(3) . . ?
C1 C11 H11 121.0 . . ?
C10 C11 H11 121.0 . . ?
N1 Cu1 O2 87.61(10) . . ?
N1 Cu1 S1 86.21(8) . . ?
N1 Cu1 S2 95.06(8) . . ?
N1 Cu1 S3 85.90(8) . . ?
O1 Cu1 N1 172.17(11) . . ?
O1 Cu1 O2 86.11(10) . . ?
O1 Cu1 S1 92.10(8) . . ?
O1 Cu1 S2 92.37(8) . . ?
O1 Cu1 S3 97.67(8) . . ?
O2 Cu1 S1 114.22(7) . . ?
O2 Cu1 S2 161.62(6) . . ?
O2 Cu1 S3 80.61(6) . . ?
S1 Cu1 S2 84.12(3) . . ?
S1 Cu1 S3 162.86(3) . . ?
S3 Cu1 S2 81.45(3) . . ?
C3 N1 C10 118.9(3) . . ?
C3 N1 Cu1 121.0(2) . . ?
C10 N1 Cu1 119.9(2) . . ?
O3 N2 O2 118.5(3) . . ?
O4 N2 O2 118.8(3) . . ?
O4 N2 O3 122.7(3) . . ?
O6 N3 O5 119.1(3) . . ?
O7 N3 O5 119.1(3) . . ?
O7 N3 O6 121.9(3) . . ?
Cu1 O1 H1A 112(2) . . ?
Cu1 O1 H1B 112(2) . . ?
H1A O1 H1B 108(3) . . ?
N2 O2 Cu1 115.1(2) . . ?
C4 S1 C5 101.58(17) . . ?
C4 S1 Cu1 95.58(11) . . ?
C5 S1 Cu1 104.34(11) . . ?
C6 S2 Cu1 92.36(11) . . ?
C7 S2 C6 104.70(16) . . ?
C7 S2 Cu1 93.60(12) . . ?
C8 S3 Cu1 105.31(12) . . ?
C9 S3 C8 101.56(17) . . ?
C9 S3 Cu1 92.64(11) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A N3 0.859(18) 2.53(2) 3.313(4) 153(3) 1_455
O1 H1A O5 0.859(18) 1.77(2) 2.612(4) 166(4) 1_455
O1 H1A O6 0.859(18) 2.63(3) 3.257(4) 131(3) 1_455
O1 H1B O2 0.854(18) 1.83(2) 2.663(3) 166(4) 3_566

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 C1 C2 C3 174.5(3) . . . . ?
Br1 C1 C11 C10 -174.8(3) . . . . ?
C1 C2 C3 C4 179.2(3) . . . . ?
C1 C2 C3 N1 0.3(5) . . . . ?
C2 C1 C11 C10 4.1(5) . . . . ?
C2 C3 C4 S1 157.5(3) . . . . ?
C2 C3 N1 C10 4.1(5) . . . . ?
C2 C3 N1 Cu1 -170.5(3) . . . . ?
C3 C4 S1 C5 -84.6(3) . . . . ?
C3 C4 S1 Cu1 21.4(3) . . . . ?
C4 C3 N1 C10 -174.9(3) . . . . ?
C4 C3 N1 Cu1 10.5(4) . . . . ?
C5 C6 S2 C7 -151.4(2) . . . . ?
C5 C6 S2 Cu1 -57.1(2) . . . . ?
C6 C5 S1 C4 68.3(3) . . . . ?
C6 C5 S1 Cu1 -30.6(3) . . . . ?
C7 C8 S3 C9 -72.2(3) . . . . ?
C7 C8 S3 Cu1 23.8(3) . . . . ?
C8 C7 S2 C6 152.9(2) . . . . ?
C8 C7 S2 Cu1 59.5(2) . . . . ?
C9 C10 C11 C1 -176.6(3) . . . . ?
C9 C10 N1 C3 172.6(3) . . . . ?
C9 C10 N1 Cu1 -12.7(4) . . . . ?
C10 C9 S3 C8 77.3(3) . . . . ?
C10 C9 S3 Cu1 -28.9(3) . . . . ?
C11 C1 C2 C3 -4.4(5) . . . . ?
C11 C10 N1 C3 -4.4(5) . . . . ?
C11 C10 N1 Cu1 170.2(3) . . . . ?
N1 C3 C4 S1 -23.4(4) . . . . ?
N1 C10 C11 C1 0.4(5) . . . . ?
O3 N2 O2 Cu1 -10.2(4) . . . . ?
O4 N2 O2 Cu1 169.5(2) . . . . ?
S1 C5 C6 S2 65.8(3) . . . . ?
S2 C7 C8 S3 -62.1(3) . . . . ?
S3 C9 C10 C11 -151.3(3) . . . . ?
S3 C9 C10 N1 31.6(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_s4155na
_database_code_depnum_ccdc_archive 'CCDC 1445161'
_audit_update_record             
;
2017-03-14 deposited with the CCDC.
2017-03-14 downloaded from the CCDC.
;
_audit_creation_date             2017-03-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H14 Br Hg I N S3, Hg I3'
_chemical_formula_sum            'C11 H14 Br Hg2 I4 N S3'
_chemical_formula_weight         1245.10
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Hg Hg -2.3894 9.2266 '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                   17.1949(11)
_cell_length_b                   8.5255(5)
_cell_length_c                   15.9682(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.274(6)
_cell_angle_gamma                90
_cell_volume                     2340.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3299
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      28.0630
_cell_measurement_theta_min      3.5320
_shelx_estimated_absorpt_T_max   0.497
_shelx_estimated_absorpt_T_min   0.163
_exptl_absorpt_coefficient_mu    20.351
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82577
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    3.534
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2168
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0661
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8124
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         3.366
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean 8.0714
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -9.00   24.00   1.0000    1.9800
omega____ theta____ kappa____ phi______ frames
    -      -22.9725  -99.0000   60.0000 33

#__ type_ start__ end____ width___ exp.time_
  2 omega  -73.00   45.00   1.0000    1.9800
omega____ theta____ kappa____ phi______ frames
    -      -22.9725   19.0000  -90.0000 118

#__ type_ start__ end____ width___ exp.time_
  3 omega -102.00  -42.00   1.0000    1.9800
omega____ theta____ kappa____ phi______ frames
    -      -22.9725 -178.0000  -90.0000 60

#__ type_ start__ end____ width___ exp.time_
  4 omega -109.00  -75.00   1.0000    1.9800
omega____ theta____ kappa____ phi______ frames
    -      -22.9725 -178.0000   90.0000 34
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3587
_reflns_number_total             4278
_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, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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    ?
_refine_diff_density_max         1.139
_refine_diff_density_min         -1.249
_refine_diff_density_rms         0.277
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         4278
_refine_ls_number_restraints     189
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0378
_refine_ls_restrained_S_all      0.986
_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)+(0.0137P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0624
_refine_ls_wR_factor_ref         0.0682
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C1) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
3. Rigid body (RIGU) restrains
 C3, Br1, C1, C2, C11, C10, C4, N1, C9, S1, Hg1, S3, C5, I1, S2, C8, C6, C7
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
4.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C11(H11)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.48780(6) 0.24730(13) 1.09931(7) 0.0234(3) Uani 1 1 d . U . . .
C1 C 0.5577(5) 0.1932(11) 1.0135(6) 0.0131(17) Uani 1 1 d . U . . .
C2 C 0.5607(5) 0.2756(12) 0.9412(6) 0.0147(18) Uani 1 1 d . U . . .
H2 H 0.5268 0.3622 0.9319 0.018 Uiso 1 1 calc R . . . .
C3 C 0.6138(5) 0.2333(11) 0.8804(6) 0.0133(17) Uani 1 1 d . U . . .
C4 C 0.6192(6) 0.3380(13) 0.8042(7) 0.023(2) Uani 1 1 d . U . . .
H4A H 0.6447 0.4368 0.8223 0.028 Uiso 1 1 calc R . . . .
H4B H 0.5655 0.3651 0.7858 0.028 Uiso 1 1 calc R . . . .
C5 C 0.7603(5) 0.3738(12) 0.7186(7) 0.024(2) Uani 1 1 d . U . . .
H5A H 0.7846 0.3665 0.6631 0.029 Uiso 1 1 calc R . . . .
H5B H 0.7483 0.4857 0.7286 0.029 Uiso 1 1 calc R . . . .
C6 C 0.8192(6) 0.3214(12) 0.7841(7) 0.025(2) Uani 1 1 d . U . . .
H6A H 0.7950 0.3207 0.8398 0.030 Uiso 1 1 calc R . . . .
H6B H 0.8633 0.3959 0.7861 0.030 Uiso 1 1 calc R . . . .
C7 C 0.9019(5) 0.0702(13) 0.8577(7) 0.025(2) Uani 1 1 d . U . . .
H7A H 0.9349 -0.0228 0.8473 0.030 Uiso 1 1 calc R . . . .
H7B H 0.9370 0.1568 0.8753 0.030 Uiso 1 1 calc R . . . .
C8 C 0.8491(6) 0.0324(12) 0.9305(7) 0.022(2) Uani 1 1 d . U . . .
H8A H 0.8145 0.1229 0.9408 0.026 Uiso 1 1 calc R . . . .
H8B H 0.8813 0.0147 0.9818 0.026 Uiso 1 1 calc R . . . .
C9 C 0.7100(5) -0.1114(12) 0.9784(6) 0.0195(19) Uani 1 1 d . U . . .
H9A H 0.6765 -0.2058 0.9753 0.023 Uiso 1 1 calc R . . . .
H9B H 0.7315 -0.1053 1.0363 0.023 Uiso 1 1 calc R . . . .
C10 C 0.6587(5) 0.0300(11) 0.9639(6) 0.0145(17) Uani 1 1 d . U . . .
C11 C 0.6067(5) 0.0651(11) 1.0263(6) 0.0135(18) Uani 1 1 d . U . . .
H11 H 0.6045 0.0039 1.0759 0.016 Uiso 1 1 calc R . . . .
Hg1 Hg 0.72655(2) -0.02468(5) 0.76406(3) 0.01981(11) Uani 1 1 d . U . . .
Hg2 Hg 0.89441(2) 0.91493(5) 0.53942(3) 0.02260(12) Uani 1 1 d . . . . .
I1 I 0.62321(4) -0.23005(8) 0.70449(4) 0.02124(17) Uani 1 1 d . U . . .
I2 I 0.88904(4) 0.71469(9) 0.67334(5) 0.02614(19) Uani 1 1 d . . . . .
I3 I 0.99309(4) 0.82862(10) 0.41216(5) 0.0381(2) Uani 1 1 d . . . . .
I4 I 0.75451(4) 1.06354(8) 0.52095(4) 0.02227(17) Uani 1 1 d . . . . .
N1 N 0.6617(4) 0.1100(9) 0.8912(5) 0.0143(14) Uani 1 1 d . U . . .
S1 S 0.66952(14) 0.2667(3) 0.71388(17) 0.0213(6) Uani 1 1 d . U . . .
S2 S 0.85475(14) 0.1252(3) 0.75981(17) 0.0207(6) Uani 1 1 d . U . . .
S3 S 0.79027(13) -0.1413(3) 0.90885(16) 0.0167(6) Uani 1 1 d . U . . .


_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 C1 1.900(10) . ?
C1 C2 1.354(13) . ?
C1 C11 1.390(12) . ?
C2 H2 0.9500 . ?
C2 C3 1.394(13) . ?
C3 C4 1.513(13) . ?
C3 N1 1.345(11) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 S1 1.804(11) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.508(12) . ?
C5 S1 1.808(9) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 S2 1.825(10) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.526(14) . ?
C7 S2 1.807(10) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 S3 1.822(10) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.508(12) . ?
C9 S3 1.809(10) . ?
C10 C11 1.386(13) . ?
C10 N1 1.349(12) . ?
C11 H11 0.9500 . ?
Hg1 I1 2.6557(7) . ?
Hg1 N1 2.604(8) . ?
Hg1 S1 2.782(3) . ?
Hg1 S2 2.550(3) . ?
Hg1 S3 2.725(2) . ?
Hg2 I2 2.7395(9) . ?
Hg2 I3 3.0089(8) 3_776 ?
Hg2 I3 2.7755(9) . ?
Hg2 I4 2.7290(8) . ?
I3 Hg2 3.0089(8) 3_776 ?

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
C2 C1 Br1 121.7(7) . . ?
C2 C1 C11 119.9(9) . . ?
C11 C1 Br1 118.4(7) . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.8(9) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 C4 117.4(9) . . ?
N1 C3 C2 121.4(9) . . ?
N1 C3 C4 121.0(9) . . ?
C3 C4 H4A 107.6 . . ?
C3 C4 H4B 107.6 . . ?
C3 C4 S1 118.9(7) . . ?
H4A C4 H4B 107.0 . . ?
S1 C4 H4A 107.6 . . ?
S1 C4 H4B 107.6 . . ?
H5A C5 H5B 107.3 . . ?
C6 C5 H5A 108.2 . . ?
C6 C5 H5B 108.2 . . ?
C6 C5 S1 116.5(8) . . ?
S1 C5 H5A 108.2 . . ?
S1 C5 H5B 108.2 . . ?
C5 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
C5 C6 S2 110.3(7) . . ?
H6A C6 H6B 108.1 . . ?
S2 C6 H6A 109.6 . . ?
S2 C6 H6B 109.6 . . ?
H7A C7 H7B 107.3 . . ?
C8 C7 H7A 108.1 . . ?
C8 C7 H7B 108.1 . . ?
C8 C7 S2 116.8(7) . . ?
S2 C7 H7A 108.1 . . ?
S2 C7 H7B 108.1 . . ?
C7 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
C7 C8 S3 111.4(7) . . ?
H8A C8 H8B 108.0 . . ?
S3 C8 H8A 109.4 . . ?
S3 C8 H8B 109.4 . . ?
H9A C9 H9B 107.1 . . ?
C10 C9 H9A 107.8 . . ?
C10 C9 H9B 107.8 . . ?
C10 C9 S3 118.0(7) . . ?
S3 C9 H9A 107.8 . . ?
S3 C9 H9B 107.8 . . ?
C11 C10 C9 116.6(9) . . ?
N1 C10 C9 120.2(9) . . ?
N1 C10 C11 123.1(9) . . ?
C1 C11 H11 121.2 . . ?
C10 C11 C1 117.6(9) . . ?
C10 C11 H11 121.2 . . ?
I1 Hg1 S1 104.88(5) . . ?
I1 Hg1 S3 108.45(6) . . ?
N1 Hg1 I1 105.99(16) . . ?
N1 Hg1 S1 71.12(18) . . ?
N1 Hg1 S3 70.77(17) . . ?
S2 Hg1 I1 153.21(7) . . ?
S2 Hg1 N1 100.66(17) . . ?
S2 Hg1 S1 81.04(8) . . ?
S2 Hg1 S3 82.75(8) . . ?
S3 Hg1 S1 134.66(8) . . ?
I2 Hg2 I3 115.98(3) . . ?
I2 Hg2 I3 106.55(3) . 3_776 ?
I3 Hg2 I3 88.90(2) . 3_776 ?
I4 Hg2 I2 109.19(3) . . ?
I4 Hg2 I3 126.57(3) . . ?
I4 Hg2 I3 104.51(3) . 3_776 ?
Hg2 I3 Hg2 91.10(2) . 3_776 ?
C3 N1 C10 118.1(9) . . ?
C3 N1 Hg1 121.1(6) . . ?
C10 N1 Hg1 118.3(6) . . ?
C4 S1 C5 103.0(5) . . ?
C4 S1 Hg1 104.1(3) . . ?
C5 S1 Hg1 98.1(3) . . ?
C6 S2 Hg1 99.2(3) . . ?
C7 S2 C6 101.5(5) . . ?
C7 S2 Hg1 102.6(3) . . ?
C8 S3 Hg1 94.3(3) . . ?
C9 S3 C8 101.4(5) . . ?
C9 S3 Hg1 99.9(3) . . ?

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 C1 C2 C3 179.1(7) . . . . ?
Br1 C1 C11 C10 -178.3(7) . . . . ?
C1 C2 C3 C4 -174.9(8) . . . . ?
C1 C2 C3 N1 1.0(14) . . . . ?
C2 C1 C11 C10 1.8(13) . . . . ?
C2 C3 C4 S1 -166.1(7) . . . . ?
C2 C3 N1 C10 -1.7(13) . . . . ?
C2 C3 N1 Hg1 159.8(7) . . . . ?
C3 C4 S1 C5 -105.2(8) . . . . ?
C3 C4 S1 Hg1 -3.3(8) . . . . ?
C4 C3 N1 C10 174.0(8) . . . . ?
C4 C3 N1 Hg1 -24.5(11) . . . . ?
C5 C6 S2 C7 -165.5(7) . . . . ?
C5 C6 S2 Hg1 -60.5(8) . . . . ?
C6 C5 S1 C4 74.9(9) . . . . ?
C6 C5 S1 Hg1 -31.7(9) . . . . ?
C7 C8 S3 C9 -157.2(7) . . . . ?
C7 C8 S3 Hg1 -56.2(7) . . . . ?
C8 C7 S2 C6 72.3(9) . . . . ?
C8 C7 S2 Hg1 -30.0(9) . . . . ?
C9 C10 C11 C1 -178.7(8) . . . . ?
C9 C10 N1 C3 178.6(8) . . . . ?
C9 C10 N1 Hg1 16.5(11) . . . . ?
C10 C9 S3 C8 63.0(8) . . . . ?
C10 C9 S3 Hg1 -33.6(8) . . . . ?
C11 C1 C2 C3 -1.0(13) . . . . ?
C11 C10 N1 C3 2.6(13) . . . . ?
C11 C10 N1 Hg1 -159.4(7) . . . . ?
N1 C3 C4 S1 18.0(12) . . . . ?
N1 C10 C11 C1 -2.7(14) . . . . ?
S1 C5 C6 S2 66.6(10) . . . . ?
S2 C7 C8 S3 64.8(10) . . . . ?
S3 C9 C10 C11 -169.0(7) . . . . ?
S3 C9 C10 N1 14.8(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_s4146na
_database_code_depnum_ccdc_archive 'CCDC 1445160'
_audit_update_record             
;
2017-03-14 deposited with the CCDC.
2017-03-14 downloaded from the CCDC.
;
_audit_creation_date             2017-03-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H15 Cl Hg N S3, Cl3 Hg'
_chemical_formula_sum            'C11 H15 Cl4 Hg2 N S3'
_chemical_formula_weight         800.40
_chemical_melting_point          ?
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'
N N 0.0311 0.0180 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Hg Hg -4.2923 7.6849 '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                   8.86244(15)
_cell_length_b                   15.5399(3)
_cell_length_c                   13.2869(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.3355(14)
_cell_angle_gamma                90
_cell_volume                     1826.80(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7915
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.1241
_cell_measurement_theta_min      2.8412
_shelx_estimated_absorpt_T_max   0.515
_shelx_estimated_absorpt_T_min   0.064
_exptl_absorpt_coefficient_mu    38.240
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.23153
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    2.910
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9572
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.292
_diffrn_reflns_theta_min         4.382
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   91.10  249.46   1.1997    6.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0000   73.8669  174.2088 132

#__ type_ start__ end____ width___ exp.time_
  2 phi     41.31  331.86   1.2006    6.0000
omega____ theta____ kappa____ phi______ frames
 169.2097  111.0000   73.8669     -     242

#__ type_ start__ end____ width___ exp.time_
  3 phi   -205.79  153.01   1.2000    3.0000
omega____ theta____ kappa____ phi______ frames
  88.2194   30.5000   73.8669     -     299

#__ type_ start__ end____ width___ exp.time_
  4 omega   90.88  246.84   1.1997    6.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   73.8669  304.2081 130

#__ type_ start__ end____ width___ exp.time_
  5 omega  104.14  234.94   1.2000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   73.8669   39.2088 109

#__ type_ start__ end____ width___ exp.time_
  6 phi    100.42  317.73   1.2006    6.0000
omega____ theta____ kappa____ phi______ frames
 119.2097  111.0000   73.8669     -     181

#__ type_ start__ end____ width___ exp.time_
  7 omega    3.78   74.60   1.2003    3.0000
omega____ theta____ kappa____ phi______ frames
    -       30.5000   73.8669  299.2100 59

#__ type_ start__ end____ width___ exp.time_
  8 phi     80.96  193.82   1.2006    3.0000
omega____ theta____ kappa____ phi______ frames
  -0.6900  -70.0000   73.8669     -     94
;
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and π scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3279
_reflns_number_total             3542
_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, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       ?
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_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    ?
_refine_diff_density_max         1.088
_refine_diff_density_min         -1.874
_refine_diff_density_rms         0.265
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3542
_refine_ls_number_restraints     174
_refine_ls_R_factor_all          0.0324
_refine_ls_R_factor_gt           0.0292
_refine_ls_restrained_S_all      1.110
_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)+(0.0450P)²+4.2155P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0788
_refine_ls_wR_factor_ref         0.0810
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid body (RIGU) restrains
 C1, C2, C11, C3, C10, C4, N1, C9, S1, Hg1, S3, C5, Cl1, S2, C8, C6, C7
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C11(H11)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
C1 C 0.6660(7) 0.8219(4) -0.0049(4) 0.0104(10) Uani 1 1 d . U . . .
H1 H 0.7547 0.7972 -0.0297 0.012 Uiso 1 1 calc R . . . .
C2 C 0.6753(6) 0.8935(4) 0.0570(4) 0.0096(10) Uani 1 1 d . U . . .
H2 H 0.7706 0.9194 0.0738 0.012 Uiso 1 1 calc R . . . .
C3 C 0.5459(6) 0.9273(4) 0.0942(4) 0.0068(9) Uani 1 1 d . U . . .
C4 C 0.5571(7) 1.0045(4) 0.1627(5) 0.0092(9) Uani 1 1 d . U . . .
H4A H 0.5389 1.0565 0.1207 0.011 Uiso 1 1 calc R . . . .
H4B H 0.6622 1.0080 0.1920 0.011 Uiso 1 1 calc R . . . .
C5 C 0.4970(7) 0.9226(4) 0.3485(5) 0.0126(9) Uani 1 1 d . U . . .
H5A H 0.6072 0.9296 0.3629 0.015 Uiso 1 1 calc R . . . .
H5B H 0.4480 0.9293 0.4132 0.015 Uiso 1 1 calc R . . . .
C6 C 0.4675(7) 0.8316(4) 0.3099(5) 0.0118(10) Uani 1 1 d . U . . .
H6A H 0.5135 0.7898 0.3589 0.014 Uiso 1 1 calc R . . . .
H6B H 0.5158 0.8239 0.2452 0.014 Uiso 1 1 calc R . . . .
C7 C 0.2638(7) 0.7199(4) 0.2042(5) 0.0146(10) Uani 1 1 d . U . . .
H7A H 0.3511 0.7249 0.1614 0.018 Uiso 1 1 calc R . . . .
H7B H 0.2752 0.6657 0.2430 0.018 Uiso 1 1 calc R . . . .
C8 C 0.1200(7) 0.7156(4) 0.1373(5) 0.0134(9) Uani 1 1 d . U . . .
H8A H 0.0334 0.7132 0.1810 0.016 Uiso 1 1 calc R . . . .
H8B H 0.1206 0.6611 0.0988 0.016 Uiso 1 1 calc R . . . .
C9 C 0.2446(6) 0.7913(4) -0.0320(5) 0.0099(9) Uani 1 1 d . U . . .
H9A H 0.2562 0.7292 -0.0460 0.012 Uiso 1 1 calc R . . . .
H9B H 0.2164 0.8197 -0.0970 0.012 Uiso 1 1 calc R . . . .
C10 C 0.3981(6) 0.8256(4) 0.0052(4) 0.0059(8) Uani 1 1 d . U . . .
C11 C 0.5259(7) 0.7870(4) -0.0300(5) 0.0107(10) Uani 1 1 d . U . . .
H11 H 0.5169 0.7369 -0.0711 0.013 Uiso 1 1 calc R . . . .
Cl1 Cl 0.03192(16) 1.05722(9) 0.13634(11) 0.0122(3) Uani 1 1 d . U . . .
Cl2 Cl 0.71287(19) 0.65348(12) 0.17045(14) 0.0235(4) Uani 1 1 d . . . . .
Cl3 Cl 0.61670(15) 0.37937(9) 0.20988(10) 0.0117(3) Uani 1 1 d . . . . .
Cl4 Cl 0.31837(17) 0.52904(12) 0.05218(12) 0.0190(3) Uani 1 1 d . . . . .
Hg1 Hg 0.19006(2) 0.93281(2) 0.16435(2) 0.00857(9) Uani 1 1 d . U . . .
Hg2 Hg 0.57866(3) 0.52313(2) 0.13901(2) 0.01525(10) Uani 1 1 d . . . . .
N1 N 0.4078(5) 0.8949(3) 0.0659(4) 0.0061(7) Uani 1 1 d . U . . .
S1 S 0.43176(16) 1.00877(10) 0.26516(11) 0.0097(3) Uani 1 1 d . U . . .
S2 S 0.26591(15) 0.81013(10) 0.29141(11) 0.0112(3) Uani 1 1 d . U . . .
S3 S 0.08758(15) 0.80343(9) 0.04824(11) 0.0085(3) Uani 1 1 d . U . . .


_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
C1 H1 0.9500 . ?
C1 C2 1.384(9) . ?
C1 C11 1.379(8) . ?
C2 H2 0.9500 . ?
C2 C3 1.378(8) . ?
C3 C4 1.506(8) . ?
C3 N1 1.356(7) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 S1 1.808(6) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.523(9) . ?
C5 S1 1.811(7) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 S2 1.820(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.512(8) . ?
C7 S2 1.818(7) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 S3 1.818(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.516(7) . ?
C9 S3 1.811(6) . ?
C10 C11 1.387(8) . ?
C10 N1 1.346(8) . ?
C11 H11 0.9500 . ?
Cl1 Hg1 2.4042(14) . ?
Cl2 Hg2 2.3738(18) . ?
Cl3 Hg2 2.4402(15) . ?
Cl4 Hg2 2.8658(16) 3_665 ?
Cl4 Hg2 2.5201(15) . ?
Hg1 N1 2.465(5) . ?
Hg1 S1 2.7281(15) . ?
Hg1 S2 2.6086(15) . ?
Hg1 S3 2.6616(15) . ?
Hg2 Cl4 2.8658(16) 3_665 ?

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
C2 C1 H1 120.6 . . ?
C11 C1 H1 120.6 . . ?
C11 C1 C2 118.8(6) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.8(5) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 C4 119.6(5) . . ?
N1 C3 C2 121.1(5) . . ?
N1 C3 C4 119.3(5) . . ?
C3 C4 H4A 107.9 . . ?
C3 C4 H4B 107.9 . . ?
C3 C4 S1 117.6(4) . . ?
H4A C4 H4B 107.2 . . ?
S1 C4 H4A 107.9 . . ?
S1 C4 H4B 107.9 . . ?
H5A C5 H5B 107.4 . . ?
C6 C5 H5A 108.3 . . ?
C6 C5 H5B 108.3 . . ?
C6 C5 S1 116.0(4) . . ?
S1 C5 H5A 108.3 . . ?
S1 C5 H5B 108.3 . . ?
C5 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
C5 C6 S2 111.3(4) . . ?
H6A C6 H6B 108.0 . . ?
S2 C6 H6A 109.4 . . ?
S2 C6 H6B 109.4 . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
C8 C7 S2 112.7(5) . . ?
S2 C7 H7A 109.0 . . ?
S2 C7 H7B 109.0 . . ?
C7 C8 H8A 108.2 . . ?
C7 C8 H8B 108.2 . . ?
C7 C8 S3 116.4(5) . . ?
H8A C8 H8B 107.3 . . ?
S3 C8 H8A 108.2 . . ?
S3 C8 H8B 108.2 . . ?
H9A C9 H9B 107.1 . . ?
C10 C9 H9A 107.7 . . ?
C10 C9 H9B 107.7 . . ?
C10 C9 S3 118.5(4) . . ?
S3 C9 H9A 107.7 . . ?
S3 C9 H9B 107.7 . . ?
C11 C10 C9 118.2(5) . . ?
N1 C10 C9 120.1(5) . . ?
N1 C10 C11 121.6(5) . . ?
C1 C11 C10 119.3(6) . . ?
C1 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
Hg2 Cl4 Hg2 93.74(5) . 3_665 ?
Cl1 Hg1 N1 125.28(12) . . ?
Cl1 Hg1 S1 99.32(5) . . ?
Cl1 Hg1 S2 144.47(5) . . ?
Cl1 Hg1 S3 109.97(5) . . ?
N1 Hg1 S1 75.36(11) . . ?
N1 Hg1 S2 89.33(12) . . ?
N1 Hg1 S3 76.31(12) . . ?
S2 Hg1 S1 80.39(5) . . ?
S2 Hg1 S3 83.65(5) . . ?
S3 Hg1 S1 147.48(4) . . ?
Cl2 Hg2 Cl3 131.05(5) . . ?
Cl2 Hg2 Cl4 102.43(6) . 3_665 ?
Cl2 Hg2 Cl4 119.04(6) . . ?
Cl3 Hg2 Cl4 92.24(5) . 3_665 ?
Cl3 Hg2 Cl4 108.20(5) . . ?
Cl4 Hg2 Cl4 86.26(5) . 3_665 ?
C3 N1 Hg1 119.1(4) . . ?
C10 N1 C3 119.2(5) . . ?
C10 N1 Hg1 119.0(4) . . ?
C4 S1 C5 104.2(3) . . ?
C4 S1 Hg1 96.52(19) . . ?
C5 S1 Hg1 101.2(2) . . ?
C6 S2 Hg1 99.6(2) . . ?
C7 S2 C6 101.6(3) . . ?
C7 S2 Hg1 99.1(2) . . ?
C8 S3 Hg1 98.9(2) . . ?
C9 S3 C8 101.9(3) . . ?
C9 S3 Hg1 99.9(2) . . ?

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
C1 C2 C3 C4 179.2(6) . . . . ?
C1 C2 C3 N1 -4.3(9) . . . . ?
C2 C1 C11 C10 1.6(9) . . . . ?
C2 C3 C4 S1 -143.0(5) . . . . ?
C2 C3 N1 C10 3.9(8) . . . . ?
C2 C3 N1 Hg1 165.2(4) . . . . ?
C3 C4 S1 C5 67.7(5) . . . . ?
C3 C4 S1 Hg1 -35.6(5) . . . . ?
C4 C3 N1 C10 -179.7(5) . . . . ?
C4 C3 N1 Hg1 -18.3(7) . . . . ?
C5 C6 S2 C7 159.3(4) . . . . ?
C5 C6 S2 Hg1 57.8(4) . . . . ?
C6 C5 S1 C4 -70.2(5) . . . . ?
C6 C5 S1 Hg1 29.5(5) . . . . ?
C7 C8 S3 C9 63.4(5) . . . . ?
C7 C8 S3 Hg1 -38.7(5) . . . . ?
C8 C7 S2 C6 -151.8(5) . . . . ?
C8 C7 S2 Hg1 -50.0(5) . . . . ?
C9 C10 C11 C1 174.0(6) . . . . ?
C9 C10 N1 C3 -176.7(5) . . . . ?
C9 C10 N1 Hg1 22.0(7) . . . . ?
C10 C9 S3 C8 -79.8(5) . . . . ?
C10 C9 S3 Hg1 21.5(5) . . . . ?
C11 C1 C2 C3 1.5(9) . . . . ?
C11 C10 N1 C3 -0.6(8) . . . . ?
C11 C10 N1 Hg1 -162.0(4) . . . . ?
N1 C3 C4 S1 40.4(7) . . . . ?
N1 C10 C11 C1 -2.1(9) . . . . ?
S1 C5 C6 S2 -62.9(6) . . . . ?
S2 C7 C8 S3 65.7(6) . . . . ?
S3 C9 C10 C11 152.7(5) . . . . ?
S3 C9 C10 N1 -31.1(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_s4137na
_database_code_depnum_ccdc_archive 'CCDC 1445159'
_audit_update_record             
;
2017-03-14 deposited with the CCDC.
2017-03-14 downloaded from the CCDC.
;
_audit_creation_date             2017-03-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'Hg I3, C26 H28 Hg I N2 S3, C H2 Cl2'
_chemical_formula_sum            'C25 H27 Cl2 Hg2 I4 N3 O S3'
_chemical_formula_weight         1461.35
_chemical_melting_point          ?
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'
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'
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'
Hg Hg -4.2923 7.6849 '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                   26.2853(4)
_cell_length_b                   8.5588(2)
_cell_length_c                   15.9777(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.033(2)
_cell_angle_gamma                90
_cell_volume                     3567.47(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5889
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.07
_cell_measurement_theta_min      5.09
_shelx_estimated_absorpt_T_max   0.462
_shelx_estimated_absorpt_T_min   0.066
_exptl_absorpt_coefficient_mu    45.621
_exptl_absorpt_correction_T_max  0.4621
_exptl_absorpt_correction_T_min  0.243375
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.721
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2640
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17878
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.588
_diffrn_reflns_theta_min         3.388
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6366
_reflns_number_total             7066
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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         2.411
_refine_diff_density_min         -2.575
_refine_diff_density_rms         0.288
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         7066
_refine_ls_number_restraints     303
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0415
_refine_ls_restrained_S_all      1.031
_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)+(0.0664P)²+20.8530P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1072
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 C00P, Hg02, I005, S007, S008, S009, N00C, C00O, C010, C00K, C00M, C00Q, C00S,
 C00E, C00F, C00G, C00J, C00L, C00R, C00U, C00X, C00N, C012, C00H, C00I, C00T,
 C00V, C011, C013, C00W, C00Y, N00D, C00Z
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
3.a Secondary CH2 refined with riding coordinates:
 C00K(H00A,H00B), C00M(H00C,H00E), C00O(H00F,H00K), C00Q(H00L,H00M), C00S(H00O,
 H00P), C010(H01A,H01B), C16(H16A,H16B)
3.b Aromatic/amide H refined with riding coordinates:
 N00D(H00D), C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J), C00N(H00N),
 C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X), C011(H011), C012(H012),
 C013(H013)
3.c Idealised Me refined as rotating group:
 C00Z(H00Q,H00R,H00S)
;
_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
Hg01 Hg 0.92966(2) 0.57418(4) 0.94708(2) 0.01801(10) Uani 1 1 d . . . . .
Hg02 Hg 0.81618(2) -0.01283(4) 1.19816(2) 0.01683(9) Uani 1 1 d . U . . .
I003 I 0.83852(2) 0.41701(6) 0.93780(3) 0.01887(12) Uani 1 1 d . . . . .
I004 I 0.92354(2) 0.78887(6) 0.81955(3) 0.02185(12) Uani 1 1 d . . . . .
I005 I 0.74609(2) -0.21748(6) 1.23447(3) 0.02253(13) Uani 1 1 d . U . . .
I006 I 0.99097(2) 0.65112(8) 1.09515(3) 0.03267(16) Uani 1 1 d . . . . .
S007 S 0.90126(6) 0.1308(2) 1.22348(12) 0.0179(3) Uani 1 1 d . U . . .
S008 S 0.86304(6) -0.1545(2) 1.07424(12) 0.0168(3) Uani 1 1 d . U . . .
S009 S 0.77837(7) 0.2812(2) 1.22593(12) 0.0169(3) Uani 1 1 d . U . . .
Cl0A Cl 0.67957(9) 0.8241(3) 0.44671(18) 0.0384(5) Uani 1 1 d . . . . .
Cl0B Cl 0.63239(10) 0.5658(3) 0.52524(18) 0.0405(5) Uani 1 1 d . . . . .
N00C N 0.7773(2) 0.0984(7) 1.0557(4) 0.0120(10) Uani 1 1 d . U . . .
N00D N 0.4509(2) 0.2438(9) 0.2508(4) 0.0220(13) Uani 1 1 d . U . . .
H00D H 0.4269 0.3159 0.2499 0.026 Uiso 1 1 calc R . . . .
C00E C 0.7457(2) 0.2209(8) 1.0523(5) 0.0126(11) Uani 1 1 d . U . . .
C00F C 0.7774(2) 0.0069(8) 0.9885(5) 0.0118(11) Uani 1 1 d . U . . .
C00G C 0.7110(3) 0.2509(9) 0.9813(5) 0.0130(12) Uani 1 1 d . U . . .
H00G H 0.6879 0.3365 0.9810 0.016 Uiso 1 1 calc R . . . .
C00H C 0.5804(3) 0.2513(10) 0.6022(5) 0.0156(12) Uani 1 1 d . U . . .
H00H H 0.5611 0.3447 0.5925 0.019 Uiso 1 1 calc R . . . .
C00I C 0.5793(3) 0.1465(9) 0.5485(5) 0.0154(12) Uani 1 1 d . U . . .
H00I H 0.5992 0.0541 0.5574 0.018 Uiso 1 1 calc R . . . .
C00J C 0.7446(3) 0.0325(9) 0.9146(5) 0.0141(12) Uani 1 1 d . U . . .
H00J H 0.7461 -0.0338 0.8672 0.017 Uiso 1 1 calc R . . . .
C00K C 0.9023(3) 0.0138(10) 1.0572(5) 0.0196(14) Uani 1 1 d . U . . .
H00A H 0.9248 -0.0113 1.0138 0.024 Uiso 1 1 calc R . . . .
H00B H 0.8799 0.1021 1.0362 0.024 Uiso 1 1 calc R . . . .
C00L C 0.7100(2) 0.1547(8) 0.9101(5) 0.0126(11) Uani 1 1 d . U . . .
C00M C 0.8115(3) -0.1361(9) 0.9893(5) 0.0182(14) Uani 1 1 d . U . . .
H00C H 0.8267 -0.1380 0.9355 0.022 Uiso 1 1 calc R . . . .
H00E H 0.7895 -0.2298 0.9900 0.022 Uiso 1 1 calc R . . . .
C00N C 0.6232(3) 0.0706(10) 0.7086(5) 0.0189(13) Uani 1 1 d . U . . .
H00N H 0.6101 -0.0172 0.6765 0.023 Uiso 1 1 calc R . . . .
C00O C 0.8788(3) 0.3213(10) 1.1845(5) 0.0215(14) Uani 1 1 d . U . . .
H00F H 0.9081 0.3948 1.1879 0.026 Uiso 1 1 calc R . . . .
H00K H 0.8642 0.3124 1.1246 0.026 Uiso 1 1 calc R . . . .
C00P C 0.6124(3) 0.2237(10) 0.6794(5) 0.0192(13) Uani 1 1 d . U . . .
C00Q C 0.7484(3) 0.3379(9) 1.1224(5) 0.0174(13) Uani 1 1 d . U . . .
H00L H 0.7130 0.3716 1.1281 0.021 Uiso 1 1 calc R . . . .
H00M H 0.7669 0.4307 1.1047 0.021 Uiso 1 1 calc R . . . .
C00R C 0.6741(3) 0.1779(10) 0.8321(5) 0.0173(12) Uani 1 1 d . U . . .
C00S C 0.8386(3) 0.3844(10) 1.2355(5) 0.0195(14) Uani 1 1 d . U . . .
H00O H 0.8316 0.4945 1.2188 0.023 Uiso 1 1 calc R . . . .
H00P H 0.8531 0.3845 1.2957 0.023 Uiso 1 1 calc R . . . .
C00T C 0.5461(3) 0.1739(10) 0.4726(5) 0.0207(14) Uani 1 1 d . U . . .
C00U C 0.6535(3) 0.0509(10) 0.7857(5) 0.0186(13) Uani 1 1 d . U . . .
H00U H 0.6602 -0.0517 0.8070 0.022 Uiso 1 1 calc R . . . .
C00V C 0.5099(3) 0.2908(11) 0.4653(6) 0.0255(16) Uani 1 1 d . U . . .
H00V H 0.5064 0.3572 0.5118 0.031 Uiso 1 1 calc R . . . .
C00W C 0.5192(3) 0.0943(12) 0.3296(6) 0.0280(17) Uani 1 1 d . U . . .
H00W H 0.5223 0.0262 0.2835 0.034 Uiso 1 1 calc R . . . .
C00X C 0.6631(3) 0.3289(10) 0.8015(5) 0.0214(14) Uani 1 1 d . U . . .
H00X H 0.6773 0.4171 0.8322 0.026 Uiso 1 1 calc R . . . .
C00Y C 0.4830(3) 0.2136(11) 0.3216(5) 0.0230(14) Uani 1 1 d . U . . .
C00Z C 0.4574(4) 0.1534(14) 0.1774(6) 0.034(2) Uani 1 1 d . U . . .
H00Q H 0.4312 0.1829 0.1312 0.051 Uiso 1 1 calc GR . . . .
H00R H 0.4541 0.0421 0.1900 0.051 Uiso 1 1 calc GR . . . .
H00S H 0.4915 0.1735 0.1607 0.051 Uiso 1 1 calc GR . . . .
C010 C 0.9350(3) 0.0619(11) 1.1388(6) 0.0230(15) Uani 1 1 d . U . . .
H01A H 0.9588 0.1453 1.1251 0.028 Uiso 1 1 calc R . . . .
H01B H 0.9562 -0.0290 1.1597 0.028 Uiso 1 1 calc R . . . .
C011 C 0.5506(4) 0.0753(12) 0.4055(6) 0.0314(19) Uani 1 1 d . U . . .
H011 H 0.5755 -0.0059 0.4111 0.038 Uiso 1 1 calc R . . . .
C012 C 0.6314(3) 0.3494(10) 0.7258(5) 0.0238(15) Uani 1 1 d . U . . .
H012 H 0.6229 0.4521 0.7062 0.029 Uiso 1 1 calc R . . . .
C013 C 0.4783(3) 0.3118(11) 0.3890(6) 0.0256(16) Uani 1 1 d . U . . .
H013 H 0.4535 0.3933 0.3836 0.031 Uiso 1 1 calc R . . . .
C16 C 0.6473(4) 0.7640(12) 0.5333(6) 0.033(2) Uani 1 1 d . . . . .
H16A H 0.6695 0.7839 0.5869 0.040 Uiso 1 1 calc R . . . .
H16B H 0.6155 0.8255 0.5339 0.040 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
Hg01 I003 2.7358(6) . ?
Hg01 I004 2.7339(6) . ?
Hg01 I006 2.7736(6) . ?
Hg01 I006 2.9785(6) 3_767 ?
Hg02 I005 2.6572(6) . ?
Hg02 S007 2.5404(18) . ?
Hg02 S008 2.7393(19) . ?
Hg02 S009 2.7617(19) . ?
Hg02 N00C 2.562(6) . ?
I006 Hg01 2.9784(6) 3_767 ?
S007 C00O 1.818(9) . ?
S007 C010 1.805(9) . ?
S008 C00K 1.811(8) . ?
S008 C00M 1.803(7) . ?
S009 C00Q 1.809(8) . ?
S009 C00S 1.803(8) . ?
Cl0A C16 1.785(11) . ?
Cl0B C16 1.743(11) . ?
N00C C00E 1.335(9) . ?
N00C C00F 1.330(10) . ?
N00D H00D 0.8800 . ?
N00D C00Y 1.351(10) . ?
N00D C00Z 1.433(12) . ?
C00E C00G 1.390(10) . ?
C00E C00Q 1.498(10) . ?
C00F C00J 1.392(10) . ?
C00F C00M 1.517(10) . ?
C00G H00G 0.9500 . ?
C00G C00L 1.402(10) . ?
C00H H00H 0.9500 . ?
C00H C00I 1.238(11) . ?
C00H C00P 1.424(10) . ?
C00I H00I 0.9500 . ?
C00I C00T 1.425(10) . ?
C00J H00J 0.9500 . ?
C00J C00L 1.383(10) . ?
C00K H00A 0.9900 . ?
C00K H00B 0.9900 . ?
C00K C010 1.528(11) . ?
C00L C00R 1.481(10) . ?
C00M H00C 0.9900 . ?
C00M H00E 0.9900 . ?
C00N H00N 0.9500 . ?
C00N C00P 1.408(12) . ?
C00N C00U 1.393(11) . ?
C00O H00F 0.9900 . ?
C00O H00K 0.9900 . ?
C00O C00S 1.512(11) . ?
C00P C012 1.367(12) . ?
C00Q H00L 0.9900 . ?
C00Q H00M 0.9900 . ?
C00R C00U 1.388(11) . ?
C00R C00X 1.400(12) . ?
C00S H00O 0.9900 . ?
C00S H00P 0.9900 . ?
C00T C00V 1.375(12) . ?
C00T C011 1.382(13) . ?
C00U H00U 0.9500 . ?
C00V H00V 0.9500 . ?
C00V C013 1.400(11) . ?
C00W H00W 0.9500 . ?
C00W C00Y 1.390(13) . ?
C00W C011 1.391(12) . ?
C00X H00X 0.9500 . ?
C00X C012 1.394(11) . ?
C00Y C013 1.383(13) . ?
C00Z H00Q 0.9800 . ?
C00Z H00R 0.9800 . ?
C00Z H00S 0.9800 . ?
C010 H01A 0.9900 . ?
C010 H01B 0.9900 . ?
C011 H011 0.9500 . ?
C012 H012 0.9500 . ?
C013 H013 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 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
I003 Hg01 I006 125.20(2) . . ?
I003 Hg01 I006 107.60(2) . 3_767 ?
I004 Hg01 I003 108.591(17) . . ?
I004 Hg01 I006 104.20(2) . 3_767 ?
I004 Hg01 I006 116.82(2) . . ?
I006 Hg01 I006 89.831(17) . 3_767 ?
I005 Hg02 S008 104.55(4) . . ?
I005 Hg02 S009 107.03(4) . . ?
S007 Hg02 I005 154.75(5) . . ?
S007 Hg02 S008 82.20(6) . . ?
S007 Hg02 S009 81.99(6) . . ?
S007 Hg02 N00C 102.10(14) . . ?
S008 Hg02 S009 136.22(6) . . ?
N00C Hg02 I005 103.12(13) . . ?
N00C Hg02 S008 71.84(14) . . ?
N00C Hg02 S009 72.04(14) . . ?
Hg01 I006 Hg01 90.170(17) . 3_767 ?
C00O S007 Hg02 97.9(3) . . ?
C010 S007 Hg02 103.1(3) . . ?
C010 S007 C00O 101.8(4) . . ?
C00K S008 Hg02 94.1(3) . . ?
C00M S008 Hg02 98.2(3) . . ?
C00M S008 C00K 101.9(4) . . ?
C00Q S009 Hg02 102.8(3) . . ?
C00S S009 Hg02 97.5(3) . . ?
C00S S009 C00Q 103.0(4) . . ?
C00E N00C Hg02 120.5(5) . . ?
C00F N00C Hg02 117.3(5) . . ?
C00F N00C C00E 119.5(6) . . ?
C00Y N00D H00D 121.4 . . ?
C00Y N00D C00Z 117.2(8) . . ?
C00Z N00D H00D 121.4 . . ?
N00C C00E C00G 121.4(7) . . ?
N00C C00E C00Q 121.4(6) . . ?
C00G C00E C00Q 117.0(6) . . ?
N00C C00F C00J 122.0(6) . . ?
N00C C00F C00M 121.9(6) . . ?
C00J C00F C00M 116.0(6) . . ?
C00E C00G H00G 120.0 . . ?
C00E C00G C00L 120.0(7) . . ?
C00L C00G H00G 120.0 . . ?
C00I C00H H00H 121.9 . . ?
C00I C00H C00P 116.2(7) . . ?
C00P C00H H00H 121.9 . . ?
C00H C00I H00I 122.2 . . ?
C00H C00I C00T 115.5(7) . . ?
C00T C00I H00I 122.2 . . ?
C00F C00J H00J 120.0 . . ?
C00L C00J C00F 119.9(7) . . ?
C00L C00J H00J 120.0 . . ?
S008 C00K H00A 109.4 . . ?
S008 C00K H00B 109.4 . . ?
H00A C00K H00B 108.0 . . ?
C010 C00K S008 110.9(6) . . ?
C010 C00K H00A 109.4 . . ?
C010 C00K H00B 109.4 . . ?
C00G C00L C00R 123.4(7) . . ?
C00J C00L C00G 117.1(6) . . ?
C00J C00L C00R 119.5(7) . . ?
S008 C00M H00C 107.9 . . ?
S008 C00M H00E 107.9 . . ?
C00F C00M S008 117.8(5) . . ?
C00F C00M H00C 107.9 . . ?
C00F C00M H00E 107.9 . . ?
H00C C00M H00E 107.2 . . ?
C00P C00N H00N 120.8 . . ?
C00U C00N H00N 120.8 . . ?
C00U C00N C00P 118.4(8) . . ?
S007 C00O H00F 109.5 . . ?
S007 C00O H00K 109.5 . . ?
H00F C00O H00K 108.1 . . ?
C00S C00O S007 110.8(6) . . ?
C00S C00O H00F 109.5 . . ?
C00S C00O H00K 109.5 . . ?
C00N C00P C00H 121.0(8) . . ?
C012 C00P C00H 118.5(8) . . ?
C012 C00P C00N 120.5(7) . . ?
S009 C00Q H00L 107.6 . . ?
S009 C00Q H00M 107.6 . . ?
C00E C00Q S009 118.7(5) . . ?
C00E C00Q H00L 107.6 . . ?
C00E C00Q H00M 107.6 . . ?
H00L C00Q H00M 107.1 . . ?
C00U C00R C00L 120.7(7) . . ?
C00U C00R C00X 119.1(7) . . ?
C00X C00R C00L 120.0(7) . . ?
S009 C00S H00O 108.2 . . ?
S009 C00S H00P 108.2 . . ?
C00O C00S S009 116.4(6) . . ?
C00O C00S H00O 108.2 . . ?
C00O C00S H00P 108.2 . . ?
H00O C00S H00P 107.4 . . ?
C00V C00T C00I 122.6(8) . . ?
C00V C00T C011 120.2(8) . . ?
C011 C00T C00I 117.2(8) . . ?
C00N C00U H00U 119.3 . . ?
C00R C00U C00N 121.4(8) . . ?
C00R C00U H00U 119.3 . . ?
C00T C00V H00V 120.0 . . ?
C00T C00V C013 119.9(8) . . ?
C013 C00V H00V 120.0 . . ?
C00Y C00W H00W 120.3 . . ?
C00Y C00W C011 119.5(9) . . ?
C011 C00W H00W 120.3 . . ?
C00R C00X H00X 120.2 . . ?
C012 C00X C00R 119.7(8) . . ?
C012 C00X H00X 120.2 . . ?
N00D C00Y C00W 124.5(9) . . ?
N00D C00Y C013 115.4(8) . . ?
C013 C00Y C00W 120.1(8) . . ?
N00D C00Z H00Q 109.5 . . ?
N00D C00Z H00R 109.5 . . ?
N00D C00Z H00S 109.5 . . ?
H00Q C00Z H00R 109.5 . . ?
H00Q C00Z H00S 109.5 . . ?
H00R C00Z H00S 109.5 . . ?
S007 C010 H01A 108.1 . . ?
S007 C010 H01B 108.1 . . ?
C00K C010 S007 116.7(5) . . ?
C00K C010 H01A 108.1 . . ?
C00K C010 H01B 108.1 . . ?
H01A C010 H01B 107.3 . . ?
C00T C011 C00W 120.4(9) . . ?
C00T C011 H011 119.8 . . ?
C00W C011 H011 119.8 . . ?
C00P C012 C00X 120.8(8) . . ?
C00P C012 H012 119.6 . . ?
C00X C012 H012 119.6 . . ?
C00V C013 H013 120.0 . . ?
C00Y C013 C00V 119.9(8) . . ?
C00Y C013 H013 120.0 . . ?
Cl0A C16 H16A 109.6 . . ?
Cl0A C16 H16B 109.6 . . ?
Cl0B C16 Cl0A 110.3(6) . . ?
Cl0B C16 H16A 109.6 . . ?
Cl0B C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_s3976ma
_database_code_depnum_ccdc_archive 'CCDC 1445150'
_audit_update_record             
;
2017-03-14 deposited with the CCDC.
2017-03-14 downloaded from the CCDC.
;
_audit_creation_date             2017-03-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C22 H19 N3 O5'
_chemical_formula_sum            'C22 H19 N3 O5'
_chemical_formula_weight         405.40
_chemical_melting_point          ?
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'
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'

_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                   4.5402(3)
_cell_length_b                   10.8201(7)
_cell_length_c                   19.7081(11)
_cell_angle_alpha                80.037(4)
_cell_angle_beta                 86.240(5)
_cell_angle_gamma                87.076(4)
_cell_volume                     950.74(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1638
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.08
_cell_measurement_theta_min      4.15
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.898
_exptl_absorpt_coefficient_mu    0.848
_exptl_absorpt_correction_T_max  0.9916
_exptl_absorpt_correction_T_min  0.778352
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_Laue_measured_fraction_full 0.952
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6897
_diffrn_reflns_point_group_measured_fraction_full 0.952
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.237
_diffrn_reflns_theta_min         4.152
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.952
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2346
_reflns_number_total             3319
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0447
_refine_ls_restrained_S_all      1.022
_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)+(0.0739P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1170
_refine_ls_wR_factor_ref         0.1285
_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), C5(H5), C6(H6), C9(H9), C10(H10), C12(H12), C13(H13),
 C15(H15), C18(H18)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C20(H20A,H20B,H20C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
C1 C 1.2425(4) 0.2801(2) 0.64112(11) 0.0244(4) Uani 1 1 d . . . . .
C2 C 1.2474(4) 0.1597(2) 0.62449(10) 0.0243(4) Uani 1 1 d . . . . .
H2 H 1.3597 0.0929 0.6498 0.029 Uiso 1 1 calc R . . . .
C3 C 1.0848(4) 0.13895(19) 0.57010(11) 0.0233(4) Uani 1 1 d . . . . .
H3 H 1.0885 0.0575 0.5582 0.028 Uiso 1 1 calc R . . . .
C4 C 0.9180(4) 0.2354(2) 0.53327(10) 0.0227(4) Uani 1 1 d . . . . .
C5 C 0.9157(5) 0.3565(2) 0.55036(11) 0.0253(4) Uani 1 1 d . . . . .
H5 H 0.8011 0.4232 0.5256 0.030 Uiso 1 1 calc R . . . .
C6 C 1.0798(5) 0.3776(2) 0.60293(11) 0.0256(5) Uani 1 1 d . . . . .
H6 H 1.0825 0.4599 0.6135 0.031 Uiso 1 1 calc R . . . .
C7 C 1.5462(5) 0.2164(2) 0.73636(11) 0.0315(5) Uani 1 1 d . . . . .
H7A H 1.4131 0.1504 0.7579 0.047 Uiso 1 1 calc GR . . . .
H7B H 1.6345 0.2521 0.7723 0.047 Uiso 1 1 calc GR . . . .
H7C H 1.7028 0.1805 0.7081 0.047 Uiso 1 1 calc GR . . . .
C8 C 0.4625(4) 0.27197(19) 0.39139(10) 0.0222(4) Uani 1 1 d . . . . .
C9 C 0.3792(4) 0.15186(19) 0.38487(10) 0.0231(4) Uani 1 1 d . . . . .
H9 H 0.4344 0.0808 0.4177 0.028 Uiso 1 1 calc R . . . .
C10 C 0.2163(4) 0.13788(19) 0.33019(10) 0.0229(4) Uani 1 1 d . . . . .
H10 H 0.1638 0.0561 0.3254 0.027 Uiso 1 1 calc R . . . .
C11 C 0.1263(4) 0.24045(19) 0.28171(10) 0.0208(4) Uani 1 1 d . . . . .
C12 C 0.2005(4) 0.36002(19) 0.29056(10) 0.0232(4) Uani 1 1 d . . . . .
H12 H 0.1365 0.4315 0.2591 0.028 Uiso 1 1 calc R . . . .
C13 C 0.3663(4) 0.37548(19) 0.34476(10) 0.0234(4) Uani 1 1 d . . . . .
H13 H 0.4149 0.4575 0.3502 0.028 Uiso 1 1 calc R . . . .
C14 C -0.0339(4) 0.22204(19) 0.22140(10) 0.0208(4) Uani 1 1 d . . . . .
C15 C 0.0008(4) 0.11027(19) 0.19498(10) 0.0226(4) Uani 1 1 d . . . . .
H15 H 0.1280 0.0441 0.2158 0.027 Uiso 1 1 calc R . . . .
C16 C -0.1510(4) 0.09610(19) 0.13814(10) 0.0221(4) Uani 1 1 d . . . . .
C17 C -0.3647(4) 0.29182(19) 0.13057(10) 0.0206(4) Uani 1 1 d . . . . .
C18 C -0.2241(4) 0.31473(18) 0.18708(10) 0.0206(4) Uani 1 1 d . . . . .
H18 H -0.2564 0.3930 0.2025 0.025 Uiso 1 1 calc R . . . .
C19 C -0.1085(4) -0.02755(19) 0.11222(10) 0.0228(4) Uani 1 1 d . . . . .
C20 C -0.2499(5) -0.1508(2) 0.03398(11) 0.0289(5) Uani 1 1 d . . . . .
H20A H -0.0461 -0.1690 0.0179 0.043 Uiso 1 1 calc GR . . . .
H20B H -0.3799 -0.1457 -0.0043 0.043 Uiso 1 1 calc GR . . . .
H20C H -0.3125 -0.2179 0.0714 0.043 Uiso 1 1 calc GR . . . .
C21 C -0.5786(4) 0.38706(19) 0.09257(10) 0.0221(4) Uani 1 1 d . . . . .
C22 C -0.8200(5) 0.58599(19) 0.09072(11) 0.0276(5) Uani 1 1 d . . . . .
H22A H -0.7387 0.6213 0.0445 0.041 Uiso 1 1 calc GR . . . .
H22B H -0.8491 0.6527 0.1187 0.041 Uiso 1 1 calc GR . . . .
H22C H -1.0098 0.5492 0.0870 0.041 Uiso 1 1 calc GR . . . .
N1 N 0.7534(4) 0.20473(16) 0.47991(9) 0.0233(4) Uani 1 1 d . . . . .
N2 N 0.6341(4) 0.29930(16) 0.44414(9) 0.0236(4) Uani 1 1 d . . . . .
N3 N -0.3312(4) 0.18435(16) 0.10517(8) 0.0211(4) Uani 1 1 d . . . . .
O1 O 1.3840(3) 0.31254(14) 0.69385(8) 0.0299(4) Uani 1 1 d . . . . .
O2 O 0.0504(4) -0.11257(14) 0.13963(8) 0.0324(4) Uani 1 1 d . . . . .
O3 O -0.2666(3) -0.03168(13) 0.05912(7) 0.0273(3) Uani 1 1 d . . . . .
O4 O -0.7010(3) 0.37369(14) 0.04264(7) 0.0279(4) Uani 1 1 d . . . . .
O5 O -0.6155(3) 0.48928(13) 0.12324(7) 0.0241(3) 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
C1 C2 1.396(3) . ?
C1 C6 1.394(3) . ?
C1 O1 1.361(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.396(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.385(3) . ?
C4 C5 1.407(3) . ?
C4 N1 1.423(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.372(3) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C7 O1 1.424(3) . ?
C8 C9 1.401(3) . ?
C8 C13 1.391(3) . ?
C8 N2 1.418(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.380(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.396(3) . ?
C11 C12 1.396(3) . ?
C11 C14 1.480(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.384(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.395(3) . ?
C14 C18 1.401(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.387(3) . ?
C16 C19 1.512(3) . ?
C16 N3 1.334(3) . ?
C17 C18 1.384(3) . ?
C17 C21 1.514(3) . ?
C17 N3 1.341(3) . ?
C18 H18 0.9500 . ?
C19 O2 1.212(2) . ?
C19 O3 1.315(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C20 O3 1.456(2) . ?
C21 O4 1.195(3) . ?
C21 O5 1.348(2) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C22 O5 1.454(2) . ?
N1 N2 1.258(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
C6 C1 C2 119.84(19) . . ?
O1 C1 C2 125.08(19) . . ?
O1 C1 C6 115.07(18) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 119.03(19) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 120.96(19) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C5 119.48(19) . . ?
C3 C4 N1 117.02(18) . . ?
C5 C4 N1 123.49(19) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.6(2) . . ?
C6 C5 H5 120.2 . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 121.0(2) . . ?
C5 C6 H6 119.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
C9 C8 N2 125.10(19) . . ?
C13 C8 C9 119.40(19) . . ?
C13 C8 N2 115.47(18) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 C8 119.27(19) . . ?
C10 C9 H9 120.4 . . ?
C9 C10 H10 119.0 . . ?
C9 C10 C11 121.92(19) . . ?
C11 C10 H10 119.0 . . ?
C10 C11 C14 120.75(18) . . ?
C12 C11 C10 118.09(19) . . ?
C12 C11 C14 121.13(18) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.66(19) . . ?
C13 C12 H12 119.7 . . ?
C8 C13 H13 119.7 . . ?
C12 C13 C8 120.56(19) . . ?
C12 C13 H13 119.7 . . ?
C15 C14 C11 121.12(18) . . ?
C15 C14 C18 116.17(18) . . ?
C18 C14 C11 122.70(18) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.78(19) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 C19 117.60(18) . . ?
N3 C16 C15 124.19(18) . . ?
N3 C16 C19 118.20(17) . . ?
C18 C17 C21 122.10(18) . . ?
N3 C17 C18 124.07(19) . . ?
N3 C17 C21 113.82(17) . . ?
C14 C18 H18 120.1 . . ?
C17 C18 C14 119.73(18) . . ?
C17 C18 H18 120.1 . . ?
O2 C19 C16 122.11(18) . . ?
O2 C19 O3 125.35(18) . . ?
O3 C19 C16 112.52(17) . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
O4 C21 C17 125.05(18) . . ?
O4 C21 O5 124.26(19) . . ?
O5 C21 C17 110.68(16) . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O5 C22 H22A 109.5 . . ?
O5 C22 H22B 109.5 . . ?
O5 C22 H22C 109.5 . . ?
N2 N1 C4 113.13(17) . . ?
N1 N2 C8 114.68(17) . . ?
C16 N3 C17 116.04(17) . . ?
C1 O1 C7 117.92(17) . . ?
C19 O3 C20 115.49(16) . . ?
C21 O5 C22 114.79(15) . . ?

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
C1 C2 C3 C4 -0.6(3) . . . . ?
C2 C1 C6 C5 2.1(3) . . . . ?
C2 C1 O1 C7 -1.1(3) . . . . ?
C2 C3 C4 C5 0.8(3) . . . . ?
C2 C3 C4 N1 -178.39(17) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C3 C4 N1 N2 -172.74(17) . . . . ?
C4 C5 C6 C1 -1.9(3) . . . . ?
C4 N1 N2 C8 -178.64(15) . . . . ?
C5 C4 N1 N2 8.1(3) . . . . ?
C6 C1 C2 C3 -0.8(3) . . . . ?
C6 C1 O1 C7 177.94(18) . . . . ?
C8 C9 C10 C11 -1.3(3) . . . . ?
C9 C8 C13 C12 -2.8(3) . . . . ?
C9 C8 N2 N1 11.5(3) . . . . ?
C9 C10 C11 C12 -1.3(3) . . . . ?
C9 C10 C11 C14 176.55(17) . . . . ?
C10 C11 C12 C13 1.9(3) . . . . ?
C10 C11 C14 C15 -26.2(3) . . . . ?
C10 C11 C14 C18 154.68(18) . . . . ?
C11 C12 C13 C8 0.1(3) . . . . ?
C11 C14 C15 C16 -179.61(18) . . . . ?
C11 C14 C18 C17 179.34(17) . . . . ?
C12 C11 C14 C15 151.60(19) . . . . ?
C12 C11 C14 C18 -27.5(3) . . . . ?
C13 C8 C9 C10 3.4(3) . . . . ?
C13 C8 N2 N1 -170.56(16) . . . . ?
C14 C11 C12 C13 -175.93(17) . . . . ?
C14 C15 C16 C19 -179.18(18) . . . . ?
C14 C15 C16 N3 0.8(3) . . . . ?
C15 C14 C18 C17 0.2(3) . . . . ?
C15 C16 C19 O2 0.3(3) . . . . ?
C15 C16 C19 O3 178.78(17) . . . . ?
C15 C16 N3 C17 -0.8(3) . . . . ?
C16 C19 O3 C20 -176.55(17) . . . . ?
C17 C21 O5 C22 -179.47(16) . . . . ?
C18 C14 C15 C16 -0.4(3) . . . . ?
C18 C17 C21 O4 178.2(2) . . . . ?
C18 C17 C21 O5 -2.5(3) . . . . ?
C18 C17 N3 C16 0.5(3) . . . . ?
C19 C16 N3 C17 179.19(17) . . . . ?
C21 C17 C18 C14 178.39(17) . . . . ?
C21 C17 N3 C16 -178.22(16) . . . . ?
N1 C4 C5 C6 179.57(18) . . . . ?
N2 C8 C9 C10 -178.76(17) . . . . ?
N2 C8 C13 C12 179.14(18) . . . . ?
N3 C16 C19 O2 -179.62(19) . . . . ?
N3 C16 C19 O3 -1.2(3) . . . . ?
N3 C17 C18 C14 -0.2(3) . . . . ?
N3 C17 C21 O4 -3.1(3) . . . . ?
N3 C17 C21 O5 176.23(16) . . . . ?
O1 C1 C2 C3 178.16(18) . . . . ?
O1 C1 C6 C5 -177.00(18) . . . . ?
O2 C19 O3 C20 1.8(3) . . . . ?
O4 C21 O5 C22 -0.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
