# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_2-Br
_database_code_depnum_ccdc_archive 'CCDC 2335394'
loop_
_audit_author_name
_audit_author_address
'Ivan Nemec'
;Palacky University
Czech Republic
;
_audit_update_record             
;
2024-02-25 deposited with the CCDC.	2024-06-24 downloaded from the CCDC.
;
_audit_creation_date             2024-02-25
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H14 Br N3 O2'
_chemical_formula_sum            'C15 H14 Br N3 O2'
_chemical_formula_weight         348.20
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     'LK Br switch'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   4.77160(10)
_cell_length_b                   18.2538(5)
_cell_length_c                   16.7147(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.171(2)
_cell_angle_gamma                90
_cell_volume                     1444.46(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6418
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      69.4500
_cell_measurement_theta_min      3.5870
_shelx_estimated_absorpt_T_max   0.827
_shelx_estimated_absorpt_T_min   0.301
_exptl_absorpt_coefficient_mu    3.956
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.57a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10145
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.709
_diffrn_reflns_theta_min         3.601
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -63.00  21.00   0.50    0.70    --  -43.63  79.00 -28.00  168
  2  ω    -20.00  47.00   0.50    0.70    --   45.19 -79.00-153.00  134
  3  ω    -84.00 -27.00   0.50    3.50    --  -93.31  79.00 -28.00  114
  4  ω   -153.00-119.00   0.50    3.50    --  -93.31 -79.00-153.00   68
  5  ω    134.00 159.00   0.50    3.50    --   94.87  79.00 -28.00   50
  6  ω     32.00 101.00   0.50    3.50    --   94.87 -79.00-153.00  138
  7  ω    -16.00  16.00   0.50    0.70    --  -43.63  32.00 -30.00   64
  8  ω   -108.00 -64.00   0.50    0.70    --  -43.63-138.00 120.00   88
  9  ω    -22.00  23.00   0.50    0.70    --  -43.63  11.00  60.00   90
 10  ω    -23.00  19.00   0.50    0.70    --   45.19 -21.00 120.00   84
 11  ω      4.00  37.00   0.50    0.70    --   45.19 -32.00  60.00   66
 12  ω     64.00 112.00   0.50    0.70    --   45.19 138.00 150.00   96
 13  ω    -24.00  28.00   0.50    0.70    --   45.19 -21.00  30.00  104
 14  ω     -4.00  27.00   0.50    0.70    --   45.19-104.00 150.00   62
 15  ω     53.00  80.00   0.50    0.70    --   45.19-104.00 150.00   54
 16  ω    -15.00  15.00   0.50    0.70    --   45.19 -21.00-120.00   60
 17  ω     73.00  98.00   0.50    0.70    --   45.19 138.00 -90.00   50
 18  ω    -57.00 -32.00   0.50    3.50    --  -93.31  50.00-180.00   50
 19  ω    -61.00 -34.00   0.50    3.50    --  -93.31  59.00 150.00   54
 20  ω   -115.00 -26.00   0.50    3.50    --  -93.31 145.00  90.00  178
 21  ω    -57.00 -32.00   0.50    3.50    --  -93.31  50.00 -90.00   50
 22  ω    -68.00 -27.00   0.50    3.50    --  -93.31  59.00 -30.00   82
 23  ω   -128.00 -80.00   0.50    3.50    --  -93.31 -17.00  30.00   96
 24  ω    -56.00 -29.00   0.50    3.50    --  -93.31  50.00  90.00   54
 25  ω    -53.00 -27.00   0.50    3.50    --  -93.31  50.00 120.00   52
 26  ω   -148.00-100.00   0.50    3.50    --  -93.31 -42.00 -90.00   96
 27  ω   -161.00 -85.00   0.50    3.50    --  -93.31 -25.00-180.00  152
 28  ω     87.00 163.00   0.50    3.50    --   94.87  25.00 -60.00  152
 29  ω     29.00  54.00   0.50    3.50    --   94.87 -50.00-120.00   50
 30  ω    126.00 153.00   0.50    3.50    --   94.87  33.00  90.00   54
 31  ω     40.00  65.00   0.50    3.50    --   94.87 -59.00-120.00   50
 32  ω     30.00  83.00   0.50    3.50    --   94.87 -68.00  30.00  106
 33  ω     32.00  69.00   0.50    3.50    --   94.87 -59.00 -30.00   74
 34  ω     29.00  54.00   0.50    3.50    --   94.87 -50.00 -90.00   50
 35  ω     32.00  62.00   0.50    3.50    --   94.87 -59.00-150.00   60
 36  ω    -47.00 -22.00   0.50    0.70    --  -43.63  79.00 -28.00   50
 37  ω     29.00  54.00   0.50    5.50    --   94.87 -50.00   0.00   50
 38  ω    -67.00 -42.00   0.50    8.00    --  -95.95  58.00 110.00   50
 39  ω   -146.00-102.00   0.50    8.00    --  -95.95 -33.00  30.00   88
 40  ω    -63.00 -37.00   0.50    8.00    --  -95.95  77.00-150.00   52
 41  ω    -63.00 -37.00   0.50    8.00    --  -95.95  59.00  60.00   52
 42  ω   -106.00 -80.00   0.50    8.00    --  -95.95  77.00-150.00   52
 43  ω    138.00 163.00   0.50    8.00    --   97.51  33.00 120.00   50
 44  ω     90.00 128.00   0.50    8.00    --   97.51  33.00 120.00   76
 45  ω     85.00 147.00   0.50    8.00    --   97.51  42.00  30.00  124
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2730996000
_diffrn_orient_matrix_UB_12      -0.0445017000
_diffrn_orient_matrix_UB_13      -0.0023734000
_diffrn_orient_matrix_UB_21      -0.1316960000
_diffrn_orient_matrix_UB_22      -0.0374862000
_diffrn_orient_matrix_UB_23      -0.0783579000
_diffrn_orient_matrix_UB_31      0.1182584000
_diffrn_orient_matrix_UB_32      0.0610881000
_diffrn_orient_matrix_UB_33      -0.0498828000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2398
_reflns_number_total             2653
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.743
_refine_diff_density_min         -0.599
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2653
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0336
_refine_ls_restrained_S_all      1.031
_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)+(0.0653P)²+0.2676P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.0945
_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.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C4(H4), C3(H3), C8(H8), C11(H11), C9(H9), C10(H10), C2(H2A), C1(H1)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.63840(5) 0.36336(2) 0.07916(2) 0.03426(13) Uani 1 1 d . . . . .
O2 O 0.5735(4) 0.37700(9) 0.48551(10) 0.0326(4) Uani 1 1 d . . . . .
O1 O 0.8653(4) 0.28265(10) 0.51635(10) 0.0390(4) Uani 1 1 d . . . . .
N2 N 0.6247(4) 0.37965(11) 0.25937(11) 0.0279(4) Uani 1 1 d . . . . .
H2 H 0.735702 0.351833 0.233984 0.033 Uiso 1 1 calc R U . . .
N3 N 0.6272(4) 0.37400(10) 0.33847(11) 0.0270(4) Uani 1 1 d . . . . .
N1 N 1.0049(4) 0.28015(11) 0.26733(12) 0.0320(4) Uani 1 1 d . . . . .
C7 C 0.4445(4) 0.43010(12) 0.21683(13) 0.0270(4) Uani 1 1 d . . . . .
C5 C 0.9990(4) 0.27708(12) 0.34786(13) 0.0271(4) Uani 1 1 d . . . . .
C6 C 0.7968(4) 0.32700(12) 0.38003(13) 0.0265(4) Uani 1 1 d . . . . .
C12 C 0.4345(5) 0.43362(12) 0.13283(13) 0.0279(4) Uani 1 1 d . . . . .
C4 C 1.1819(5) 0.22898(12) 0.39526(14) 0.0306(5) Uani 1 1 d . . . . .
H4 H 1.179202 0.226404 0.451920 0.037 Uiso 1 1 calc R U . . .
C13 C 0.7541(5) 0.32559(12) 0.46688(13) 0.0283(5) Uani 1 1 d . . . . .
C3 C 1.3642(5) 0.18589(13) 0.35845(15) 0.0343(5) Uani 1 1 d . . . . .
H3 H 1.488425 0.153335 0.389862 0.041 Uiso 1 1 calc R U . . .
C8 C 0.2741(5) 0.47761(13) 0.25453(14) 0.0316(5) Uani 1 1 d . . . . .
H8 H 0.271522 0.474868 0.311192 0.038 Uiso 1 1 calc R U . . .
C11 C 0.2710(5) 0.48540(13) 0.08833(14) 0.0325(5) Uani 1 1 d . . . . .
H11 H 0.269510 0.487704 0.031496 0.039 Uiso 1 1 calc R U . . .
C9 C 0.1083(5) 0.52884(14) 0.20956(15) 0.0353(5) Uani 1 1 d . . . . .
H9 H -0.007798 0.560955 0.235753 0.042 Uiso 1 1 calc R U . . .
C10 C 0.1093(5) 0.53392(14) 0.12689(15) 0.0355(5) Uani 1 1 d . . . . .
H10 H -0.000129 0.570408 0.096868 0.043 Uiso 1 1 calc R U . . .
C2 C 1.3679(5) 0.18960(14) 0.27575(15) 0.0350(5) Uani 1 1 d . . . . .
H2A H 1.493350 0.160237 0.249577 0.042 Uiso 1 1 calc R U . . .
C1 C 1.1823(5) 0.23762(14) 0.23285(15) 0.0360(5) Uani 1 1 d . . . . .
H1 H 1.181214 0.240430 0.176055 0.043 Uiso 1 1 calc R U . . .
C14 C 0.5063(5) 0.37542(14) 0.56785(14) 0.0349(5) Uani 1 1 d . . . . .
H14A H 0.679431 0.382367 0.606349 0.042 Uiso 1 1 calc R U . . .
H14B H 0.420111 0.327842 0.579385 0.042 Uiso 1 1 calc R U . . .
C15 C 0.3007(5) 0.43712(14) 0.57540(15) 0.0390(6) Uani 1 1 d . . . . .
H15A H 0.133883 0.430581 0.535493 0.058 Uiso 1 1 calc R U . . .
H15B H 0.391308 0.483970 0.565910 0.058 Uiso 1 1 calc R U . . .
H15C H 0.243493 0.436886 0.629708 0.058 Uiso 1 1 calc R 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 C12 1.901(2) . ?
O2 C13 1.337(3) . ?
O2 C14 1.452(3) . ?
O1 C13 1.213(3) . ?
N2 N3 1.325(3) . ?
N2 C7 1.393(3) . ?
N3 C6 1.316(3) . ?
N1 C5 1.351(3) . ?
N1 C1 1.332(3) . ?
C7 C12 1.400(3) . ?
C7 C8 1.392(3) . ?
C5 C6 1.477(3) . ?
C5 C4 1.410(3) . ?
C6 C13 1.491(3) . ?
C12 C11 1.382(3) . ?
C4 C3 1.374(4) . ?
C3 C2 1.386(4) . ?
C8 C9 1.385(3) . ?
C11 C10 1.386(4) . ?
C9 C10 1.386(4) . ?
C2 C1 1.381(4) . ?
C14 C15 1.509(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O2 C14 115.59(18) . . ?
N3 N2 C7 119.27(19) . . ?
C6 N3 N2 120.37(19) . . ?
C1 N1 C5 120.0(2) . . ?
N2 C7 C12 118.9(2) . . ?
C8 C7 N2 122.6(2) . . ?
C8 C7 C12 118.5(2) . . ?
N1 C5 C6 115.65(19) . . ?
N1 C5 C4 119.8(2) . . ?
C4 C5 C6 124.5(2) . . ?
N3 C6 C5 126.6(2) . . ?
N3 C6 C13 112.04(19) . . ?
C5 C6 C13 121.25(19) . . ?
C7 C12 Br1 119.13(17) . . ?
C11 C12 Br1 119.68(17) . . ?
C11 C12 C7 121.1(2) . . ?
C3 C4 C5 119.1(2) . . ?
O2 C13 C6 112.64(18) . . ?
O1 C13 O2 122.4(2) . . ?
O1 C13 C6 125.0(2) . . ?
C4 C3 C2 120.4(2) . . ?
C9 C8 C7 120.1(2) . . ?
C12 C11 C10 119.8(2) . . ?
C8 C9 C10 120.9(2) . . ?
C11 C10 C9 119.5(2) . . ?
C1 C2 C3 117.5(2) . . ?
N1 C1 C2 123.1(2) . . ?
O2 C14 C15 106.7(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.677
_oxdiff_exptl_absorpt_empirical_full_min 0.517
####################################################################### 
# 
# 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_2-I
_database_code_depnum_ccdc_archive 'CCDC 2335397'
loop_
_audit_author_name
_audit_author_address
'Ivan Nemec'
;Palacky University
Czech Republic
;
_audit_update_record             
;
2024-02-25 deposited with the CCDC.	2024-06-24 downloaded from the CCDC.
;
_audit_creation_date             2023-10-18
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H14 I N3 O2'
_chemical_formula_sum            'C15 H14 I N3 O2'
_chemical_formula_weight         395.19
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C60  H56  I4  N12  O8  '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   4.6839(2)
_cell_length_b                   18.5687(8)
_cell_length_c                   16.9966(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.506(4)
_cell_angle_gamma                90
_cell_volume                     1471.44(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4465
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      69.3040
_cell_measurement_theta_min      3.4770
_shelx_estimated_absorpt_T_max   0.340
_shelx_estimated_absorpt_T_min   0.086
_exptl_absorpt_coefficient_mu    17.176
_exptl_absorpt_correction_T_max  0.396
_exptl_absorpt_correction_T_min  0.119
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.57a (Rigaku Oxford Diffraction, 2022)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.784
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 -2 0.0422
0 -1 1 0.0397
0 1 -1 0.0360
0 -2 1 0.0392
0 2 -1 0.0417
0 -1 0 0.0391
0 1 0 0.0417
2 1 0 0.1260
-1 1 0 0.1424
1 2 0 0.1217
0 0 1 0.0399
0 -1 -2 0.0475
-1 -1 2 0.1255
-1 0 2 0.1336
1 0 -2 0.1214
0 -1 -1 0.0452
0 1 2 0.0337

_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0005 1.0016 -1.9997 0.0785 0.1822 0.0269
-0.0007 -1.0006 0.9996 -0.0148 -0.1175 -0.0340
0.0007 1.0006 -0.9996 0.0148 0.1175 0.0340
-0.0015 -2.0001 0.9991 0.0342 -0.1702 -0.0752
0.0015 2.0001 -0.9991 -0.0342 0.1702 0.0752
-0.0008 -0.9996 -0.0005 0.0490 -0.0528 -0.0412
0.0008 0.9996 0.0005 -0.0490 0.0528 0.0412
2.0014 0.9903 -0.0047 0.1703 -0.1891 0.6159
-0.9994 1.0042 0.0032 -0.1586 0.1737 -0.2462
1.0019 1.9945 -0.0015 0.0117 -0.0154 0.3697
0.0002 -0.0010 1.0001 -0.0637 -0.0647 0.0071
-0.0011 -0.9976 -2.0008 0.1764 0.0766 -0.0554
-1.0008 -0.9969 2.0024 -0.1881 -0.0612 -0.3143
-0.9999 0.0027 2.0029 -0.2371 -0.0085 -0.2731
0.9999 -0.0027 -2.0029 0.2371 0.0085 0.2731
-0.0010 -0.9986 -1.0007 0.1127 0.0119 -0.0483
0.0011 0.9976 2.0008 -0.1764 -0.0766 0.0554

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7046
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.574
_diffrn_reflns_theta_min         3.534
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -34.00  23.00   0.50    2.00    --  -43.25  81.00  14.00  114
  2  ω     -9.00  28.00   0.50    2.00    --   44.82 -81.00-108.00   74
  3  ω   -120.00 -94.00   0.50    6.00    --  -95.95  81.00  14.00   52
  4  ω   -151.00 -78.00   0.50    6.00    --  -95.95 -81.00-108.00  146
  5  ω     52.00  78.00   0.50    6.00    --   97.51 -81.00-108.00   52
  6  ω    122.00 147.00   0.50    6.00    --   97.51  81.00  14.00   50
  7  ω   -108.00 -28.00   0.50    2.00    --  -43.25 -54.00  90.00  160
  8  ω    -99.00 -74.00   0.50    2.00    --  -43.25-138.00   0.00   50
  9  ω    -19.00  22.00   0.50    2.00    --  -43.25  11.00  30.00   82
 10  ω   -108.00 -73.00   0.50    2.00    --  -43.25-138.00-150.00   70
 11  ω    -78.00 -49.00   0.50    2.00    --  -43.25 -32.00 -90.00   58
 12  ω   -108.00 -83.00   0.50    2.00    --  -43.25 -32.00 -90.00   50
 13  ω     -5.00  34.00   0.50    2.00    --   44.82 -32.00-120.00   78
 14  ω    -13.00  14.00   0.50    2.00    --   44.82 -21.00-180.00   54
 15  ω    -14.00  35.00   0.50    2.00    --   44.82 -32.00   0.00   98
 16  ω    -81.00 -51.00   0.50    6.00    --  -95.95  68.00  90.00   60
 17  ω   -163.00 -88.00   0.50    6.00    --  -95.95 -25.00-180.00  150
 18  ω   -118.00 -81.00   0.50    6.00    --  -95.95-117.00 -30.00   74
 19  ω    -88.00 -38.00   0.50    6.00    --  -95.95  81.00  14.00  100
 20  ω    -68.00 -32.00   0.50    6.00    --  -95.95  59.00   0.00   72
 21  ω   -106.00 -45.00   0.50    6.00    --  -95.95  96.00 120.00  122
 22  ω   -158.00 -79.00   0.50    6.00    --  -95.95 -86.00 -30.00  158
 23  ω   -161.00-126.00   0.50    6.00    --  -95.95-117.00 -30.00   70
 24  ω   -151.00-101.00   0.50    6.00    --  -95.95 -96.00 -60.00  100
 25  ω     31.00  56.00   0.50    6.00    --   97.51 -59.00-150.00   50
 26  ω     55.00  82.00   0.50    6.00    --   97.51 -68.00-120.00   54
 27  ω     31.00  56.00   0.50    6.00    --   97.51 -50.00 150.00   50
 28  ω     31.00  56.00   0.50    6.00    --   97.51 -50.00 -30.00   50
 29  ω     31.00  57.00   0.50    6.00    --   97.51 -50.00  90.00   52
 30  ω     81.00 163.00   0.50    6.00    --   97.51  50.00  60.00  164
 31  ω     31.00  56.00   0.50    6.00    --   97.51 -50.00-120.00   50
 32  ω     34.00  59.00   0.50    6.00    --   97.51 -68.00  30.00   50
 33  ω     34.00  63.00   0.50    6.00    --   97.51 -59.00 -90.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1091821000
_diffrn_orient_matrix_UB_12      -0.0490319000
_diffrn_orient_matrix_UB_13      -0.0637898000
_diffrn_orient_matrix_UB_21      -0.1208190000
_diffrn_orient_matrix_UB_22      0.0529245000
_diffrn_orient_matrix_UB_23      -0.0646209000
_diffrn_orient_matrix_UB_31      0.2874846000
_diffrn_orient_matrix_UB_32      0.0409427000
_diffrn_orient_matrix_UB_33      0.0071153000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2461
_reflns_number_total             2730
_reflns_odcompleteness_completeness 99.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         1.217
_refine_diff_density_min         -2.092
_refine_diff_density_rms         0.197
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2730
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0550
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1215P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1458
_refine_ls_wR_factor_ref         0.1492
_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.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C10(H10), C8(H8), C6(H6), C5(H5), C9(H9), C3(H3A), C4(H4), C7(H7)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.36498(7) 0.64388(2) 0.92807(2) 0.0354(2) Uani 1 1 d . . . . .
O2 O 0.4391(8) 0.6204(2) 0.5201(2) 0.0378(8) Uani 1 1 d . . . . .
O1 O 0.1459(9) 0.7129(2) 0.4925(2) 0.0423(9) Uani 1 1 d . . . . .
N3 N 0.3725(10) 0.6148(2) 0.7431(2) 0.0333(9) Uani 1 1 d . . . . .
H3 H 0.259647 0.642385 0.768627 0.040 Uiso 1 1 calc R U . . .
N2 N 0.3737(9) 0.6206(2) 0.6654(2) 0.0317(9) Uani 1 1 d . . . . .
N1 N -0.0048(10) 0.7148(2) 0.7380(2) 0.0353(9) Uani 1 1 d . . . . .
C1 C 0.5515(11) 0.5645(3) 0.7841(3) 0.0310(10) Uani 1 1 d . . . . .
C10 C -0.1741(11) 0.7664(3) 0.6139(3) 0.0350(11) Uani 1 1 d . . . . .
H10 H -0.167335 0.769094 0.558254 0.042 Uiso 1 1 calc R U . . .
C11 C 0.0034(11) 0.7177(3) 0.6592(3) 0.0312(10) Uani 1 1 d . . . . .
C8 C -0.3626(12) 0.8061(3) 0.7326(3) 0.0377(11) Uani 1 1 d . . . . .
H8 H -0.487219 0.835883 0.759196 0.045 Uiso 1 1 calc R U . . .
C2 C 0.5679(11) 0.5632(3) 0.8667(3) 0.0326(10) Uani 1 1 d . . . . .
C6 C 0.7126(12) 0.5153(3) 0.7454(3) 0.0349(11) Uani 1 1 d . . . . .
H6 H 0.707147 0.516218 0.689414 0.042 Uiso 1 1 calc R U . . .
C5 C 0.8817(12) 0.4648(3) 0.7885(3) 0.0370(11) Uani 1 1 d . . . . .
H5 H 0.992735 0.431652 0.761602 0.044 Uiso 1 1 calc R U . . .
C12 C 0.2068(12) 0.6679(3) 0.6260(3) 0.0335(10) Uani 1 1 d . . . . .
C9 C -0.3572(12) 0.8099(3) 0.6508(3) 0.0382(11) Uani 1 1 d . . . . .
H9 H -0.479853 0.842566 0.620727 0.046 Uiso 1 1 calc R U . . .
C3 C 0.7325(12) 0.5117(3) 0.9089(3) 0.0360(11) Uani 1 1 d . . . . .
H3A H 0.736942 0.510317 0.964854 0.043 Uiso 1 1 calc R U . . .
C13 C 0.2570(12) 0.6697(3) 0.5402(3) 0.0342(11) Uani 1 1 d . . . . .
C4 C 0.8900(12) 0.4622(3) 0.8705(3) 0.0378(11) Uani 1 1 d . . . . .
H4 H 1.002477 0.426896 0.899702 0.045 Uiso 1 1 calc R U . . .
C7 C -0.1804(12) 0.7574(3) 0.7737(3) 0.0403(12) Uani 1 1 d . . . . .
H7 H -0.180910 0.754465 0.829483 0.048 Uiso 1 1 calc R U . . .
C14 C 0.5131(13) 0.6225(3) 0.4386(3) 0.0393(11) Uani 1 1 d . . . . .
H14A H 0.604739 0.669048 0.427862 0.047 Uiso 1 1 calc R U . . .
H14B H 0.338116 0.617183 0.401462 0.047 Uiso 1 1 calc R U . . .
C15 C 0.7153(14) 0.5619(3) 0.4280(3) 0.0470(14) Uani 1 1 d . . . . .
H15A H 0.777717 0.563852 0.374656 0.070 Uiso 1 1 calc R U . . .
H15B H 0.618332 0.515999 0.435409 0.070 Uiso 1 1 calc R U . . .
H15C H 0.882517 0.566183 0.467051 0.070 Uiso 1 1 calc R 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
I1 C2 2.104(5) . ?
O2 C13 1.319(7) . ?
O2 C14 1.460(6) . ?
O1 C13 1.220(6) . ?
N3 H3 0.8800 . ?
N3 N2 1.326(6) . ?
N3 C1 1.395(6) . ?
N2 C12 1.316(7) . ?
N1 C11 1.345(6) . ?
N1 C7 1.329(7) . ?
C1 C2 1.399(6) . ?
C1 C6 1.391(7) . ?
C10 H10 0.9500 . ?
C10 C11 1.407(7) . ?
C10 C9 1.374(8) . ?
C11 C12 1.478(7) . ?
C8 H8 0.9500 . ?
C8 C9 1.394(8) . ?
C8 C7 1.385(8) . ?
C2 C3 1.385(7) . ?
C6 H6 0.9500 . ?
C6 C5 1.390(7) . ?
C5 H5 0.9500 . ?
C5 C4 1.393(7) . ?
C12 C13 1.499(7) . ?
C9 H9 0.9500 . ?
C3 H3A 0.9500 . ?
C3 C4 1.380(8) . ?
C4 H4 0.9500 . ?
C7 H7 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.492(8) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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
C13 O2 C14 116.5(4) . . ?
N2 N3 H3 120.2 . . ?
N2 N3 C1 119.5(4) . . ?
C1 N3 H3 120.2 . . ?
C12 N2 N3 120.2(4) . . ?
C7 N1 C11 120.5(5) . . ?
N3 C1 C2 119.1(5) . . ?
C6 C1 N3 122.0(4) . . ?
C6 C1 C2 118.9(4) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.3(5) . . ?
N1 C11 C10 120.0(5) . . ?
N1 C11 C12 115.9(4) . . ?
C10 C11 C12 124.1(4) . . ?
C9 C8 H8 121.1 . . ?
C7 C8 H8 121.1 . . ?
C7 C8 C9 117.9(5) . . ?
C1 C2 I1 120.1(4) . . ?
C3 C2 I1 119.4(4) . . ?
C3 C2 C1 120.4(5) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 C1 120.2(4) . . ?
C5 C6 H6 119.9 . . ?
C6 C5 H5 119.7 . . ?
C6 C5 C4 120.7(5) . . ?
C4 C5 H5 119.7 . . ?
N2 C12 C11 126.6(4) . . ?
N2 C12 C13 111.7(4) . . ?
C11 C12 C13 121.7(4) . . ?
C10 C9 C8 119.8(5) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C2 C3 H3A 119.6 . . ?
C4 C3 C2 120.8(5) . . ?
C4 C3 H3A 119.6 . . ?
O2 C13 C12 113.7(4) . . ?
O1 C13 O2 121.9(5) . . ?
O1 C13 C12 124.3(5) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 C5 119.0(5) . . ?
C3 C4 H4 120.5 . . ?
N1 C7 C8 122.5(5) . . ?
N1 C7 H7 118.8 . . ?
C8 C7 H7 118.8 . . ?
O2 C14 H14A 110.2 . . ?
O2 C14 H14B 110.2 . . ?
O2 C14 C15 107.8(4) . . ?
H14A C14 H14B 108.5 . . ?
C15 C14 H14A 110.2 . . ?
C15 C14 H14B 110.2 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.076
_oxdiff_exptl_absorpt_empirical_full_min 0.466
####################################################################### 
# 
# 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_2-Inosph
_database_code_depnum_ccdc_archive 'CCDC 2335396'
loop_
_audit_author_name
_audit_author_address
'Ivan Nemec'
;Palacky University
Czech Republic
;
_audit_update_record             
;
2024-02-25 deposited with the CCDC.	2024-06-24 downloaded from the CCDC.
;
_audit_creation_date             2023-10-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_chemical_formula_moiety         'C15 H14 I N3 O2'
_chemical_formula_sum            'C15 H14 I N3 O2'
_chemical_formula_weight         395.202
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01788 0.00908 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
I -0.29566 6.85062 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.03110 0.01806 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.04960 0.03234 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   4.6839(2)
_cell_length_b                   18.5687(8)
_cell_length_c                   16.9966(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.506(4)
_cell_angle_gamma                90
_cell_volume                     1471.44(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4465
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      69.3040
_cell_measurement_theta_min      3.4770
_exptl_absorpt_coefficient_mu    17.179
_exptl_absorpt_correction_T_max  0.396
_exptl_absorpt_correction_T_min  0.119
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.57a (Rigaku Oxford Diffraction, 2022)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.784
_exptl_crystal_F_000             779.013
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 -2 0.0422
0 -1 1 0.0397
0 1 -1 0.0360
0 -2 1 0.0392
0 2 -1 0.0417
0 -1 0 0.0391
0 1 0 0.0417
2 1 0 0.1260
-1 1 0 0.1424
1 2 0 0.1217
0 0 1 0.0399
0 -1 -2 0.0475
-1 -1 2 0.1255
-1 0 2 0.1336
1 0 -2 0.1214
0 -1 -1 0.0452
0 1 2 0.0337

_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_crystal_description       ribon
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 0.9929
_diffrn_reflns_Laue_measured_fraction_max 0.9845
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            7046
_diffrn_reflns_point_group_measured_fraction_full 0.9929
_diffrn_reflns_point_group_measured_fraction_max 0.9845
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         69.57
_diffrn_reflns_theta_min         3.53
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.9929
_diffrn_measured_fraction_theta_max 0.9845
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -34.00  23.00   0.50    2.00    --  -43.25  81.00  14.00  114
  2  ω     -9.00  28.00   0.50    2.00    --   44.82 -81.00-108.00   74
  3  ω   -120.00 -94.00   0.50    6.00    --  -95.95  81.00  14.00   52
  4  ω   -151.00 -78.00   0.50    6.00    --  -95.95 -81.00-108.00  146
  5  ω     52.00  78.00   0.50    6.00    --   97.51 -81.00-108.00   52
  6  ω    122.00 147.00   0.50    6.00    --   97.51  81.00  14.00   50
  7  ω   -108.00 -28.00   0.50    2.00    --  -43.25 -54.00  90.00  160
  8  ω    -99.00 -74.00   0.50    2.00    --  -43.25-138.00   0.00   50
  9  ω    -19.00  22.00   0.50    2.00    --  -43.25  11.00  30.00   82
 10  ω   -108.00 -73.00   0.50    2.00    --  -43.25-138.00-150.00   70
 11  ω    -78.00 -49.00   0.50    2.00    --  -43.25 -32.00 -90.00   58
 12  ω   -108.00 -83.00   0.50    2.00    --  -43.25 -32.00 -90.00   50
 13  ω     -5.00  34.00   0.50    2.00    --   44.82 -32.00-120.00   78
 14  ω    -13.00  14.00   0.50    2.00    --   44.82 -21.00-180.00   54
 15  ω    -14.00  35.00   0.50    2.00    --   44.82 -32.00   0.00   98
 16  ω    -81.00 -51.00   0.50    6.00    --  -95.95  68.00  90.00   60
 17  ω   -163.00 -88.00   0.50    6.00    --  -95.95 -25.00-180.00  150
 18  ω   -118.00 -81.00   0.50    6.00    --  -95.95-117.00 -30.00   74
 19  ω    -88.00 -38.00   0.50    6.00    --  -95.95  81.00  14.00  100
 20  ω    -68.00 -32.00   0.50    6.00    --  -95.95  59.00   0.00   72
 21  ω   -106.00 -45.00   0.50    6.00    --  -95.95  96.00 120.00  122
 22  ω   -158.00 -79.00   0.50    6.00    --  -95.95 -86.00 -30.00  158
 23  ω   -161.00-126.00   0.50    6.00    --  -95.95-117.00 -30.00   70
 24  ω   -151.00-101.00   0.50    6.00    --  -95.95 -96.00 -60.00  100
 25  ω     31.00  56.00   0.50    6.00    --   97.51 -59.00-150.00   50
 26  ω     55.00  82.00   0.50    6.00    --   97.51 -68.00-120.00   54
 27  ω     31.00  56.00   0.50    6.00    --   97.51 -50.00 150.00   50
 28  ω     31.00  56.00   0.50    6.00    --   97.51 -50.00 -30.00   50
 29  ω     31.00  57.00   0.50    6.00    --   97.51 -50.00  90.00   52
 30  ω     81.00 163.00   0.50    6.00    --   97.51  50.00  60.00  164
 31  ω     31.00  56.00   0.50    6.00    --   97.51 -50.00-120.00   50
 32  ω     34.00  59.00   0.50    6.00    --   97.51 -68.00  30.00   50
 33  ω     34.00  63.00   0.50    6.00    --   97.51 -59.00 -90.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              5
_reflns_limit_h_min              -5
_reflns_limit_k_max              22
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                2461
_reflns_number_total             2730
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         1.1937
_refine_diff_density_min         -2.1192
_refine_diff_density_rms         0.2077
_refine_ls_d_res_high            0.8226
_refine_ls_d_res_low             12.5058
_refine_ls_goodness_of_fit_ref   1.0120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    2
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2730
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0539
_refine_ls_restrained_S_all      1.0120
_refine_ls_shift/su_max          0.0010
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1238P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1424
_refine_ls_wR_factor_ref         0.1459
_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. Uiso/Uaniso restraints and constraints
Uanis(H15b) = Uanis(H15c) = Uanis(H15a) = Uanis(H14a) = Uanis(H14b)
Uanis(H10) = Uanis(H9) = Uanis(H8) = Uanis(H7) = Uanis(H3) = Uanis(H6) =
Uanis(H5) = Uanis(H4) = Uanis(H3a)
;
_olex2_refine_details            
;
Refinement using NoSpherA2, an implementation of
NOn-SPHERical Atom-form-factors in Olex2.
Please cite:
F. Kleemiss et al. Chem. Sci. DOI 10.1039/D0SC05526C - 2021
NoSpherA2 implementation of HAR makes use of
tailor-made aspherical atomic form factors calculated
on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
spherical-atom form factors.

The ED is calculated from a gaussian basis set single determinant SCF
wavefunction - either Hartree-Fock or DFT using selected funtionals
 - for a fragment of the crystal.
This fragment can be embedded in an electrostatic crystal field
 by employing cluster charges
or modelled using implicit solvation models, depending on the software used.
The following options were used:
   SOFTWARE:       ORCA
   PARTITIONING:   NoSpherA2
   INT ACCURACY:   High
   METHOD:         B3LYP
   BASIS SET:      x2c-TZVPP
   CHARGE:         0
   MULTIPLICITY:   1
   RELATIVISTIC:   DKH2
   DATE:           2023-10-18_20-39-56
;
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_refinement_flags_posn
I1 I 0.36497(7) 0.643880(16) 0.928075(16) 0.0351(2) Uani 1.000000 .
O2 O 0.4393(8) 0.6203(2) 0.51987(19) 0.0379(8) Uani 1.000000 .
O1 O 0.1461(9) 0.7128(2) 0.4926(2) 0.0425(9) Uani 1.000000 .
N3 N 0.3723(10) 0.6148(2) 0.7429(2) 0.0338(9) Uani 1.000000 .
H3 H 0.280(18) 0.657(4) 0.769(4) 0.062(6) Uani 1.000000 .
N2 N 0.3727(9) 0.6208(2) 0.6658(2) 0.0313(8) Uani 1.000000 .
N1 N -0.0051(9) 0.7148(2) 0.7377(2) 0.0349(9) Uani 1.000000 .
C1 C 0.5509(11) 0.5647(3) 0.7842(3) 0.0305(10) Uani 1.000000 .
C10 C -0.1729(11) 0.7663(3) 0.6136(3) 0.0344(10) Uani 1.000000 .
H10 H -0.168(15) 0.767(4) 0.550(3) 0.062(6) Uani 1.000000 .
C11 C 0.0037(11) 0.7178(3) 0.6593(3) 0.0309(10) Uani 1.000000 .
C8 C -0.3636(12) 0.8062(3) 0.7326(3) 0.0377(11) Uani 1.000000 .
H8 H -0.513(16) 0.836(4) 0.764(4) 0.062(6) Uani 1.000000 .
C2 C 0.5674(11) 0.5634(3) 0.8666(3) 0.0322(10) Uani 1.000000 .
C6 C 0.7117(12) 0.5153(3) 0.7451(3) 0.0346(11) Uani 1.000000 .
H6 H 0.725(15) 0.520(4) 0.685(4) 0.062(6) Uani 1.000000 .
C5 C 0.8830(12) 0.4646(3) 0.7884(3) 0.0370(11) Uani 1.000000 .
H5 H 1.044(15) 0.430(4) 0.760(3) 0.062(6) Uani 1.000000 .
C12 C 0.2061(12) 0.6679(3) 0.6257(3) 0.0332(10) Uani 1.000000 .
C9 C -0.3573(12) 0.8102(3) 0.6508(3) 0.0387(11) Uani 1.000000 .
H9 H -0.537(16) 0.841(4) 0.618(4) 0.062(6) Uani 1.000000 .
C3 C 0.7315(12) 0.5119(3) 0.9092(3) 0.0364(11) Uani 1.000000 .
H3a H 0.759(14) 0.510(4) 0.975(3) 0.062(6) Uani 1.000000 .
C13 C 0.2568(12) 0.6698(3) 0.5402(3) 0.0348(11) Uani 1.000000 .
C4 C 0.8904(12) 0.4623(3) 0.8704(3) 0.0382(11) Uani 1.000000 .
H4 H 1.002(15) 0.428(4) 0.908(4) 0.062(6) Uani 1.000000 .
C7 C -0.1802(12) 0.7574(3) 0.7737(3) 0.0407(12) Uani 1.000000 .
H7 H -0.172(14) 0.751(4) 0.839(3) 0.062(6) Uani 1.000000 .
C14 C 0.5123(14) 0.6227(3) 0.4389(3) 0.0396(12) Uani 1.000000 .
H14a H 0.302(15) 0.618(4) 0.399(6) 0.078(11) Uani 1.000000 .
H14b H 0.621(15) 0.672(4) 0.428(5) 0.078(11) Uani 1.000000 .
C15 C 0.7160(15) 0.5618(3) 0.4282(3) 0.0465(14) Uani 1.000000 .
H15a H 0.766(16) 0.566(4) 0.366(6) 0.078(11) Uani 1.000000 .
H15b H 0.928(16) 0.566(4) 0.466(6) 0.078(11) Uani 1.000000 .
H15c H 0.610(15) 0.510(4) 0.437(5) 0.078(11) Uani 1.000000 .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C2 2.100(5) . ?
O2 C13 1.323(7) . ?
O2 C14 1.450(6) . ?
O1 C13 1.216(6) . ?
N3 H3 1.02(8) . ?
N3 N2 1.316(6) . ?
N3 C1 1.394(6) . ?
N2 C12 1.317(7) . ?
N1 C11 1.339(6) . ?
N1 C7 1.330(7) . ?
C1 C2 1.396(6) . ?
C1 C6 1.395(7) . ?
C10 H10 1.09(6) . ?
C10 C11 1.405(7) . ?
C10 C9 1.383(8) . ?
C11 C12 1.479(7) . ?
C8 H8 1.07(7) . ?
C8 C9 1.396(7) . ?
C8 C7 1.390(8) . ?
C2 C3 1.388(7) . ?
C6 H6 1.03(6) . ?
C6 C5 1.399(7) . ?
C5 H5 1.14(6) . ?
C5 C4 1.392(7) . ?
C12 C13 1.495(7) . ?
C9 H9 1.13(7) . ?
C3 H3a 1.12(6) . ?
C3 C4 1.389(8) . ?
C4 H4 1.00(7) . ?
C7 H7 1.12(6) . ?
C14 H14a 1.15(7) . ?
C14 H14b 1.07(7) . ?
C14 C15 1.502(8) . ?
C15 H15a 1.12(11) . ?
C15 H15b 1.14(7) . ?
C15 H15c 1.09(7) . ?

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
C14 O2 C13 116.3(4) . . ?
N2 N3 H3 115(4) . . ?
C1 N3 H3 123(4) . . ?
C1 N3 N2 119.9(4) . . ?
C12 N2 N3 121.0(4) . . ?
C7 N1 C11 120.9(5) . . ?
C2 C1 N3 119.3(5) . . ?
C6 C1 N3 121.7(4) . . ?
C6 C1 C2 119.1(4) . . ?
C11 C10 H10 120(4) . . ?
C9 C10 H10 121(3) . . ?
C9 C10 C11 119.1(5) . . ?
C10 C11 N1 120.2(5) . . ?
C12 C11 N1 116.1(4) . . ?
C12 C11 C10 123.6(4) . . ?
C9 C8 H8 123(4) . . ?
C7 C8 H8 119(4) . . ?
C7 C8 C9 117.7(5) . . ?
C1 C2 I1 120.2(4) . . ?
C3 C2 I1 119.0(4) . . ?
C3 C2 C1 120.7(5) . . ?
H6 C6 C1 120(4) . . ?
C5 C6 C1 120.1(4) . . ?
C5 C6 H6 119(4) . . ?
H5 C5 C6 122(3) . . ?
C4 C5 C6 120.4(5) . . ?
C4 C5 H5 117(3) . . ?
C11 C12 N2 125.8(4) . . ?
C13 C12 N2 112.2(4) . . ?
C13 C12 C11 121.8(4) . . ?
C8 C9 C10 119.8(5) . . ?
H9 C9 C10 123(3) . . ?
H9 C9 C8 116(3) . . ?
H3a C3 C2 124(3) . . ?
C4 C3 C2 120.3(5) . . ?
C4 C3 H3a 116(3) . . ?
O1 C13 O2 121.9(5) . . ?
C12 C13 O2 113.8(4) . . ?
C12 C13 O1 124.3(5) . . ?
C3 C4 C5 119.4(5) . . ?
H4 C4 C5 128(4) . . ?
H4 C4 C3 113(4) . . ?
C8 C7 N1 122.3(5) . . ?
H7 C7 N1 116(3) . . ?
H7 C7 C8 122(3) . . ?
H14a C14 O2 107(5) . . ?
H14b C14 O2 110(5) . . ?
H14b C14 H14a 111(5) . . ?
C15 C14 O2 107.6(4) . . ?
C15 C14 H14a 113(4) . . ?
C15 C14 H14b 108(4) . . ?
H15a C15 C14 105(4) . . ?
H15b C15 C14 115(4) . . ?
H15b C15 H15a 107(6) . . ?
H15c C15 C14 110(4) . . ?
H15c C15 H15a 110(6) . . ?
H15c C15 H15b 111(5) . . ?

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
I1 C2 C1 N3 -7.3(4) . . . . ?
I1 C2 C1 C6 173.3(4) . . . . ?
I1 C2 C3 C4 -173.7(4) . . . . ?
O2 C13 C12 N2 5.3(5) . . . . ?
O2 C13 C12 C11 -178.5(4) . . . . ?
O1 C13 C12 N2 -173.8(6) . . . . ?
O1 C13 C12 C11 2.4(6) . . . . ?
N3 N2 C12 C11 -0.5(5) . . . . ?
N3 N2 C12 C13 175.5(5) . . . . ?
N3 C1 C2 C3 176.7(4) . . . . ?
N3 C1 C6 C5 -178.4(5) . . . . ?
N2 C12 C11 N1 1.0(6) . . . . ?
N2 C12 C11 C10 -179.0(5) . . . . ?
N1 C11 C10 C9 -0.7(6) . . . . ?
N1 C11 C12 C13 -174.6(4) . . . . ?
N1 C7 C8 C9 -0.7(7) . . . . ?
C1 C2 C3 C4 2.3(6) . . . . ?
C1 C6 C5 C4 1.1(6) . . . . ?
C10 C11 C12 C13 5.4(6) . . . . ?
C10 C9 C8 C7 0.1(6) . . . . ?
C2 C3 C4 C5 -0.2(6) . . . . ?
C6 C5 C4 C3 -1.6(6) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
####################################################################### 
# 
# 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_2-Brnosph
_database_code_depnum_ccdc_archive 'CCDC 2335395'
loop_
_audit_author_name
_audit_author_address
'Ivan Nemec'
;Palacky University
Czech Republic
;
_audit_update_record             
;
2024-02-25 deposited with the CCDC.	2024-06-24 downloaded from the CCDC.
;
_audit_creation_date             2023-11-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_chemical_formula_moiety         'C15 H14 Br N3 O2'
_chemical_formula_sum            'C15 H14 Br N3 O2'
_chemical_formula_weight         348.201
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
Br -0.66955 1.28295 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
C 0.01788 0.00908 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.03110 0.01806 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.04960 0.03234 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   4.7709(1)
_cell_length_b                   18.2539(5)
_cell_length_c                   16.7122(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.166(2)
_cell_angle_gamma                90
_cell_volume                     1444.06(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6427
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      69.4440
_cell_measurement_theta_min      3.5880
_exptl_absorpt_coefficient_mu    3.957
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55432
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.57a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.602
_exptl_crystal_description       needle
_exptl_crystal_F_000             703.370
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.9981
_diffrn_reflns_Laue_measured_fraction_max 0.9761
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10084
_diffrn_reflns_point_group_measured_fraction_full 0.9981
_diffrn_reflns_point_group_measured_fraction_max 0.9761
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         69.73
_diffrn_reflns_theta_min         3.60
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.9981
_diffrn_measured_fraction_theta_max 0.9761
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -63.00  21.00   0.50    0.70    --  -43.63  79.00 -28.00  168
  2  ω    -20.00  47.00   0.50    0.70    --   45.19 -79.00-153.00  134
  3  ω    -84.00 -27.00   0.50    3.50    --  -93.31  79.00 -28.00  114
  4  ω   -153.00-119.00   0.50    3.50    --  -93.31 -79.00-153.00   68
  5  ω    134.00 159.00   0.50    3.50    --   94.87  79.00 -28.00   50
  6  ω     32.00 101.00   0.50    3.50    --   94.87 -79.00-153.00  138
  7  ω    -16.00  16.00   0.50    0.70    --  -43.63  32.00 -30.00   64
  8  ω   -108.00 -64.00   0.50    0.70    --  -43.63-138.00 120.00   88
  9  ω    -22.00  23.00   0.50    0.70    --  -43.63  11.00  60.00   90
 10  ω    -23.00  19.00   0.50    0.70    --   45.19 -21.00 120.00   84
 11  ω      4.00  37.00   0.50    0.70    --   45.19 -32.00  60.00   66
 12  ω     64.00 112.00   0.50    0.70    --   45.19 138.00 150.00   96
 13  ω    -24.00  28.00   0.50    0.70    --   45.19 -21.00  30.00  104
 14  ω     -4.00  27.00   0.50    0.70    --   45.19-104.00 150.00   62
 15  ω     53.00  80.00   0.50    0.70    --   45.19-104.00 150.00   54
 16  ω    -15.00  15.00   0.50    0.70    --   45.19 -21.00-120.00   60
 17  ω     73.00  98.00   0.50    0.70    --   45.19 138.00 -90.00   50
 18  ω    -57.00 -32.00   0.50    3.50    --  -93.31  50.00-180.00   50
 19  ω    -61.00 -34.00   0.50    3.50    --  -93.31  59.00 150.00   54
 20  ω   -115.00 -26.00   0.50    3.50    --  -93.31 145.00  90.00  178
 21  ω    -57.00 -32.00   0.50    3.50    --  -93.31  50.00 -90.00   50
 22  ω    -68.00 -27.00   0.50    3.50    --  -93.31  59.00 -30.00   82
 23  ω   -128.00 -80.00   0.50    3.50    --  -93.31 -17.00  30.00   96
 24  ω    -56.00 -29.00   0.50    3.50    --  -93.31  50.00  90.00   54
 25  ω    -53.00 -27.00   0.50    3.50    --  -93.31  50.00 120.00   52
 26  ω   -148.00-100.00   0.50    3.50    --  -93.31 -42.00 -90.00   96
 27  ω   -161.00 -85.00   0.50    3.50    --  -93.31 -25.00-180.00  152
 28  ω     87.00 163.00   0.50    3.50    --   94.87  25.00 -60.00  152
 29  ω     29.00  54.00   0.50    3.50    --   94.87 -50.00-120.00   50
 30  ω    126.00 153.00   0.50    3.50    --   94.87  33.00  90.00   54
 31  ω     40.00  65.00   0.50    3.50    --   94.87 -59.00-120.00   50
 32  ω     30.00  83.00   0.50    3.50    --   94.87 -68.00  30.00  106
 33  ω     32.00  69.00   0.50    3.50    --   94.87 -59.00 -30.00   74
 34  ω     29.00  54.00   0.50    3.50    --   94.87 -50.00 -90.00   50
 35  ω     32.00  62.00   0.50    3.50    --   94.87 -59.00-150.00   60
 36  ω    -47.00 -22.00   0.50    0.70    --  -43.63  79.00 -28.00   50
 37  ω     29.00  54.00   0.50    5.50    --   94.87 -50.00   0.00   50
 38  ω    -67.00 -42.00   0.50    8.00    --  -95.95  58.00 110.00   50
 39  ω   -146.00-102.00   0.50    8.00    --  -95.95 -33.00  30.00   88
 40  ω    -63.00 -37.00   0.50    8.00    --  -95.95  77.00-150.00   52
 41  ω    -63.00 -37.00   0.50    8.00    --  -95.95  59.00  60.00   52
 42  ω   -106.00 -80.00   0.50    8.00    --  -95.95  77.00-150.00   52
 43  ω    138.00 163.00   0.50    8.00    --   97.51  33.00 120.00   50
 44  ω     90.00 128.00   0.50    8.00    --   97.51  33.00 120.00   76
 45  ω     85.00 147.00   0.50    8.00    --   97.51  42.00  30.00  124
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              5
_reflns_limit_h_min              -5
_reflns_limit_k_max              22
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                2367
_reflns_number_total             2654
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.57a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.7666
_refine_diff_density_min         -0.8299
_refine_diff_density_rms         0.0795
_refine_ls_d_res_high            0.8218
_refine_ls_d_res_low             12.2737
_refine_ls_goodness_of_fit_ref   1.0296
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     316
_refine_ls_number_reflns         2654
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0321
_refine_ls_restrained_S_all      1.0296
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0624P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.0868
_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
;
_olex2_refine_details            
;
Refinement using NoSpherA2, an implementation of
NOn-SPHERical Atom-form-factors in Olex2.
Please cite:
F. Kleemiss et al. Chem. Sci. DOI 10.1039/D0SC05526C - 2021
NoSpherA2 implementation of HAR makes use of
tailor-made aspherical atomic form factors calculated
on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
spherical-atom form factors.

The ED is calculated from a gaussian basis set single determinant SCF
wavefunction - either Hartree-Fock or DFT using selected funtionals
 - for a fragment of the crystal.
This fragment can be embedded in an electrostatic crystal field by employing cluster charges
or modelled using implicit solvation models, depending on the software used.
The following options were used:
   SOFTWARE:       ORCA
   PARTITIONING:   NoSpherA2
   INT ACCURACY:   Normal
   METHOD:         B3LYP
   BASIS SET:      def2-TZVP
   CHARGE:         0
   MULTIPLICITY:   1
   DATE:           2023-11-10_22-52-59
;
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_refinement_flags_posn
Br1 Br 0.63840(5) 0.636626(13) 0.079176(13) 0.03530(13) Uani 1.000000 .
O2 O 0.5735(3) 0.62315(9) 0.48584(9) 0.0344(4) Uani 1.000000 .
O1 O 0.8657(4) 0.71734(10) 0.51627(10) 0.0406(4) Uani 1.000000 .
N2 N 0.6244(4) 0.62034(11) 0.25954(12) 0.0301(4) Uani 1.000000 .
H2 H 0.746(7) 0.6525(19) 0.232(2) 0.050(8) Uani 1.000000 .
N3 N 0.6282(4) 0.62616(10) 0.33794(11) 0.0282(4) Uani 1.000000 .
N1 N 1.0054(4) 0.72000(11) 0.26767(11) 0.0331(4) Uani 1.000000 .
C6 C 0.4457(4) 0.57003(12) 0.21674(13) 0.0278(4) Uani 1.000000 .
C8 C 0.9987(4) 0.72274(12) 0.34785(13) 0.0287(4) Uani 1.000000 .
C1 C 0.4353(4) 0.56655(12) 0.13277(13) 0.0287(4) Uani 1.000000 .
C7 C 0.7968(4) 0.67288(12) 0.38013(12) 0.0280(4) Uani 1.000000 .
C13 C 0.7539(4) 0.67436(12) 0.46692(13) 0.0294(5) Uani 1.000000 .
C9 C 1.1816(5) 0.77094(12) 0.39552(14) 0.0326(5) Uani 1.000000 .
H9 H 1.169(7) 0.7724(18) 0.4637(17) 0.062(8) Uani 1.000000 .
C5 C 0.2740(5) 0.52236(13) 0.25486(15) 0.0333(5) Uani 1.000000 .
H5 H 0.279(7) 0.5288(17) 0.3223(16) 0.062(9) Uani 1.000000 .
C4 C 0.1079(5) 0.47110(14) 0.20980(15) 0.0369(5) Uani 1.000000 .
H4 H -0.016(7) 0.4352(17) 0.242(2) 0.073(10) Uani 1.000000 .
C10 C 1.3651(5) 0.81429(13) 0.35856(15) 0.0358(5) Uani 1.000000 .
H10 H 1.507(8) 0.8514(18) 0.395(2) 0.076(11) Uani 1.000000 .
C2 C 0.2719(5) 0.51465(13) 0.08808(16) 0.0344(5) Uani 1.000000 .
H2a H 0.273(6) 0.5129(16) 0.0239(19) 0.063(8) Uani 1.000000 .
C11 C 1.3684(5) 0.81041(14) 0.27567(15) 0.0369(5) Uani 1.000000 .
H11 H 1.511(7) 0.8427(18) 0.2469(19) 0.065(9) Uani 1.000000 .
C3 C 0.1089(5) 0.46598(14) 0.12697(15) 0.0370(5) Uani 1.000000 .
H3 H -0.023(5) 0.4252(15) 0.0913(17) 0.052(7) Uani 1.000000 .
C14 C 0.5067(6) 0.62445(15) 0.56779(15) 0.0365(5) Uani 1.000000 .
H14a H 0.692(6) 0.6199(19) 0.603(2) 0.068(10) Uani 1.000000 .
H14b H 0.421(8) 0.6796(16) 0.581(2) 0.074(10) Uani 1.000000 .
C12 C 1.1821(5) 0.76232(14) 0.23253(15) 0.0379(5) Uani 1.000000 .
H12 H 1.169(8) 0.755(2) 0.1657(15) 0.079(11) Uani 1.000000 .
C15 C 0.3006(6) 0.56289(15) 0.57553(16) 0.0413(6) Uani 1.000000 .
H15a H 0.115(8) 0.572(2) 0.529(2) 0.086(11) Uani 1.000000 .
H15b H 0.381(7) 0.5052(19) 0.5684(18) 0.072(10) Uani 1.000000 .
H15c H 0.232(7) 0.5618(19) 0.6379(17) 0.068(9) Uani 1.000000 .


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 1.896(2) . ?
O2 C13 1.335(3) . ?
O2 C14 1.445(3) . ?
O1 C13 1.213(3) . ?
N2 H2 0.98(4) . ?
N2 N3 1.312(3) . ?
N2 C6 1.389(3) . ?
N3 C7 1.316(3) . ?
N1 C8 1.345(3) . ?
N1 C12 1.333(3) . ?
C6 C1 1.399(3) . ?
C6 C5 1.402(3) . ?
C8 C7 1.475(3) . ?
C8 C9 1.413(3) . ?
C1 C2 1.385(3) . ?
C7 C13 1.490(3) . ?
C9 H9 1.15(3) . ?
C9 C10 1.382(3) . ?
C5 H5 1.13(3) . ?
C5 C4 1.386(3) . ?
C4 H4 1.07(3) . ?
C4 C3 1.388(4) . ?
C10 H10 1.09(3) . ?
C10 C11 1.389(4) . ?
C2 H2a 1.07(3) . ?
C2 C3 1.394(4) . ?
C11 H11 1.06(3) . ?
C11 C12 1.386(3) . ?
C3 H3 1.10(3) . ?
C14 H14a 1.00(3) . ?
C14 H14b 1.12(3) . ?
C14 C15 1.509(4) . ?
C12 H12 1.12(2) . ?
C15 H15a 1.12(4) . ?
C15 H15b 1.13(3) . ?
C15 H15c 1.13(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
C14 O2 C13 115.98(18) . . ?
N3 N2 H2 119(2) . . ?
C6 N2 H2 121(2) . . ?
C6 N2 N3 119.9(2) . . ?
C7 N3 N2 121.3(2) . . ?
C12 N1 C8 120.8(2) . . ?
C1 C6 N2 119.3(2) . . ?
C5 C6 N2 122.2(2) . . ?
C5 C6 C1 118.6(2) . . ?
C7 C8 N1 116.03(19) . . ?
C9 C8 N1 119.7(2) . . ?
C9 C8 C7 124.3(2) . . ?
C6 C1 Br1 119.14(16) . . ?
C2 C1 Br1 119.55(17) . . ?
C2 C1 C6 121.3(2) . . ?
C8 C7 N3 125.99(19) . . ?
C13 C7 N3 112.60(19) . . ?
C13 C7 C8 121.33(18) . . ?
O1 C13 O2 122.25(19) . . ?
C7 C13 O2 112.88(18) . . ?
C7 C13 O1 124.9(2) . . ?
H9 C9 C8 118.0(16) . . ?
C10 C9 C8 119.1(2) . . ?
C10 C9 H9 122.9(16) . . ?
H5 C5 C6 116.5(13) . . ?
C4 C5 C6 119.9(2) . . ?
C4 C5 H5 123.5(13) . . ?
H4 C4 C5 116.9(19) . . ?
C3 C4 C5 120.9(2) . . ?
C3 C4 H4 122.1(19) . . ?
H10 C10 C9 119.2(18) . . ?
C11 C10 C9 120.2(2) . . ?
C11 C10 H10 120.6(18) . . ?
H2a C2 C1 119.0(14) . . ?
C3 C2 C1 119.6(2) . . ?
C3 C2 H2a 121.4(14) . . ?
H11 C11 C10 120.8(18) . . ?
C12 C11 C10 117.7(2) . . ?
C12 C11 H11 121.5(18) . . ?
C2 C3 C4 119.6(2) . . ?
H3 C3 C4 120.9(14) . . ?
H3 C3 C2 119.5(14) . . ?
H14a C14 O2 106(2) . . ?
H14b C14 O2 109.3(16) . . ?
H14b C14 H14a 106(3) . . ?
C15 C14 O2 107.0(2) . . ?
C15 C14 H14a 115(2) . . ?
C15 C14 H14b 113.4(19) . . ?
C11 C12 N1 122.5(2) . . ?
H12 C12 N1 114.5(18) . . ?
H12 C12 C11 123.0(18) . . ?
H15a C15 C14 107.6(19) . . ?
H15b C15 C14 117(2) . . ?
H15b C15 H15a 108(3) . . ?
H15c C15 C14 111.0(17) . . ?
H15c C15 H15a 111(3) . . ?
H15c C15 H15b 103(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
Br1 C1 C6 N2 -5.85(19) . . . . ?
Br1 C1 C6 C5 174.08(17) . . . . ?
Br1 C1 C2 C3 -176.07(17) . . . . ?
O2 C13 C7 N3 6.1(2) . . . . ?
O2 C13 C7 C8 -177.02(16) . . . . ?
O1 C13 C7 N3 -173.1(2) . . . . ?
O1 C13 C7 C8 3.7(3) . . . . ?
N2 N3 C7 C8 -0.6(2) . . . . ?
N2 N3 C7 C13 176.1(2) . . . . ?
N2 C6 C1 C2 176.5(2) . . . . ?
N2 C6 C5 C4 -177.4(2) . . . . ?
N3 C7 C8 N1 0.9(2) . . . . ?
N3 C7 C8 C9 -178.4(2) . . . . ?
N1 C8 C7 C13 -175.54(18) . . . . ?
N1 C8 C9 C10 -0.2(2) . . . . ?
N1 C12 C11 C10 -0.7(3) . . . . ?
C6 C1 C2 C3 1.6(3) . . . . ?
C6 C5 C4 C3 0.1(3) . . . . ?
C8 C9 C10 C11 0.1(2) . . . . ?
C1 C2 C3 C4 1.3(3) . . . . ?
C9 C10 C11 C12 0.3(3) . . . . ?
C5 C4 C3 C2 -2.2(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
