# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_yy_a
_audit_block_doi                 10.5517/ccdc.csd.cc2ddfjs
_database_code_depnum_ccdc_archive 'CCDC 2216485'
loop_
_audit_author_name
_audit_author_address
'guoyan li'
;University of  jinan
China
;
_audit_update_record             
;
2022-10-31 deposited with the CCDC.	2024-01-09 downloaded from the CCDC.
;
_audit_creation_date             2022-07-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H7 Br O S'
_chemical_formula_sum            'C13 H7 Br O S'
_chemical_formula_weight         291.16
_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'
S S 0.1246 0.1234 '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 -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   28.9708(13)
_cell_length_b                   3.86710(10)
_cell_length_c                   20.0178(9)
_cell_angle_alpha                90
_cell_angle_beta                 105.170(2)
_cell_angle_gamma                90
_cell_volume                     2164.50(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   0.890
_shelx_estimated_absorpt_T_min   0.364
_exptl_absorpt_coefficient_mu    3.962
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.787
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14057
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.026
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         2.860
_diffrn_ambient_temperature      170(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_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                1742
_reflns_number_total             1869
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.844
_refine_diff_density_min         -1.588
_refine_diff_density_rms         0.164
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         1869
_refine_ls_number_restraints     52
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0876
_refine_ls_restrained_S_all      1.098
_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)+(0.3100P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3244
_refine_ls_wR_factor_ref         0.3333
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C13A-O1A
 1.2 with sigma of 0.02
 C13B-O1B
 1.2 with sigma of 0.02
 C9-C13B
 1.5 with sigma of 0.02
 C1-C13A
 1.5 with sigma of 0.02
2. Uiso/Uaniso restraints and constraints
C9 \\sim C13B \\sim C1 \\sim C13A \\sim O1B \\sim O1A: within 2A with sigma of
0.001 and sigma for terminal atoms of 0.002 within 2A
Uanis(C13A) \\sim Ueq, Uanis(C13B) \\sim Ueq, Uanis(O1A) \\sim Ueq, Uanis(O1B)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Sof(O1B)=Sof(C13B)=Sof(H13B)=1-FVAR(1)
 Sof(O1A)=Sof(C13A)=Sof(H13A)=FVAR(1)
 Sof(Br1)=1-FVAR(2)
 Sof(Br2)=FVAR(2)
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C8(H8), C10(H10), C11(H11), C13A(H13A), C13B(H13B)
;
_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
S1 S 0.31646(6) 0.2006(5) 0.51956(8) 0.0373(7) Uani 1 1 d . . . . .
C1 C 0.4660(3) 0.6113(19) 0.6002(4) 0.0438(16) Uani 1 1 d D U . . .
C2 C 0.4409(2) 0.4766(16) 0.6461(3) 0.0331(14) Uani 1 1 d . . . . .
H2 H 0.454552 0.468729 0.694734 0.040 Uiso 1 1 calc R U . . .
C3 C 0.3946(2) 0.3553(16) 0.6158(4) 0.0316(14) Uani 1 1 d . . . . .
C4 C 0.3749(2) 0.3715(16) 0.5455(3) 0.0334(14) Uani 1 1 d . . . . .
C5 C 0.3996(3) 0.510(2) 0.5016(4) 0.0416(16) Uani 1 1 d . . . . .
H5 H 0.385466 0.523767 0.453150 0.050 Uiso 1 1 calc R U . . .
C6 C 0.4460(3) 0.6306(19) 0.5303(4) 0.0413(16) Uani 1 1 d . . . . .
H6 H 0.463837 0.726519 0.501158 0.050 Uiso 1 1 calc R U . . .
C7 C 0.3611(2) 0.2006(16) 0.6517(4) 0.0303(14) Uani 1 1 d . . . . .
C8 C 0.3674(3) 0.149(2) 0.7222(4) 0.0380(15) Uani 1 1 d . . . . .
H8 H 0.396057 0.218772 0.754604 0.046 Uiso 1 1 calc R U . . .
C9 C 0.3308(3) -0.008(2) 0.7443(4) 0.0413(15) Uani 1 1 d D U . . .
C10 C 0.2884(3) -0.1161(17) 0.6967(4) 0.0401(16) Uani 1 1 d . . . . .
H10 H 0.264480 -0.232016 0.712888 0.048 Uiso 1 1 calc R U . . .
C11 C 0.2813(3) -0.0571(19) 0.6284(4) 0.0434(17) Uani 1 1 d . . . . .
H11 H 0.252086 -0.120300 0.596383 0.052 Uiso 1 1 calc R U . . .
C12 C 0.3179(2) 0.0993(16) 0.6062(3) 0.0321(14) Uani 1 1 d . . . . .
O1A O 0.5347(5) 0.748(3) 0.6755(10) 0.048(2) Uani 0.502(16) 1 d D U P A 1
Br1 Br 0.53036(6) 0.7577(3) 0.63878(11) 0.0374(8) Uani 0.531(5) 1 d . . P A 3
C13A C 0.5166(6) 0.762(5) 0.6170(10) 0.0447(17) Uani 0.502(16) 1 d D U P A 1
H13A H 0.531102 0.855551 0.583544 0.054 Uiso 0.502(16) 1 calc R U P A 1
O1B O 0.3511(6) -0.048(4) 0.8582(8) 0.045(2) Uani 0.498(16) 1 d D U P A 2
Br2 Br 0.33603(7) -0.0846(5) 0.83791(10) 0.0403(8) Uani 0.469(5) 1 d . . P A 4
C13B C 0.3238(7) -0.093(5) 0.8109(8) 0.0424(16) Uani 0.498(16) 1 d D U P A 2
H13B H 0.294281 -0.192535 0.813208 0.051 Uiso 0.498(16) 1 calc R U P A 2


_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
S1 C4 1.764(7) . ?
S1 C12 1.768(7) . ?
C1 C2 1.413(10) . ?
C1 C6 1.369(11) . ?
C1 Br1 1.908(7) . ?
C1 C13A 1.531(17) . ?
C2 H2 0.9500 . ?
C2 C3 1.400(9) . ?
C3 C4 1.374(10) . ?
C3 C7 1.476(9) . ?
C4 C5 1.381(10) . ?
C5 H5 0.9500 . ?
C5 C6 1.396(11) . ?
C6 H6 0.9500 . ?
C7 C8 1.390(10) . ?
C7 C12 1.397(10) . ?
C8 H8 0.9500 . ?
C8 C9 1.388(11) . ?
C9 C10 1.409(11) . ?
C9 Br2 1.863(7) . ?
C9 C13B 1.438(15) . ?
C10 H10 0.9500 . ?
C10 C11 1.347(12) . ?
C11 H11 0.9500 . ?
C11 C12 1.392(11) . ?
O1A C13A 1.153(18) . ?
C13A H13A 0.9500 . ?
O1B C13B 1.077(18) . ?
C13B H13B 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
C12 S1 C4 91.1(3) . . ?
C2 C1 Br1 117.5(5) . . ?
C2 C1 C13A 128.7(10) . . ?
C6 C1 C2 122.2(7) . . ?
C6 C1 Br1 120.3(6) . . ?
C6 C1 C13A 109.1(10) . . ?
C1 C2 H2 122.0 . . ?
C3 C2 C1 116.0(6) . . ?
C3 C2 H2 122.0 . . ?
C2 C3 C7 127.0(6) . . ?
C4 C3 C2 121.5(6) . . ?
C4 C3 C7 111.5(6) . . ?
C3 C4 S1 113.2(5) . . ?
C5 C4 S1 125.2(5) . . ?
C5 C4 C3 121.6(6) . . ?
C4 C5 H5 120.9 . . ?
C4 C5 C6 118.1(7) . . ?
C6 C5 H5 120.9 . . ?
C1 C6 C5 120.5(7) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C8 C7 C3 128.7(7) . . ?
C8 C7 C12 118.6(6) . . ?
C12 C7 C3 112.8(6) . . ?
C7 C8 H8 120.7 . . ?
C7 C8 C9 118.6(7) . . ?
C9 C8 H8 120.7 . . ?
C8 C9 C10 121.1(7) . . ?
C8 C9 Br2 121.5(6) . . ?
C8 C9 C13B 134.4(10) . . ?
C10 C9 Br2 117.4(6) . . ?
C10 C9 C13B 104.4(9) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.7(7) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 H11 120.9 . . ?
C10 C11 C12 118.1(7) . . ?
C12 C11 H11 120.9 . . ?
C7 C12 S1 111.4(5) . . ?
C11 C12 S1 125.8(5) . . ?
C11 C12 C7 122.8(7) . . ?
C1 C13A H13A 124.5 . . ?
O1A C13A C1 111.1(16) . . ?
O1A C13A H13A 124.5 . . ?
C9 C13B H13B 119.0 . . ?
O1B C13B C9 121.9(18) . . ?
O1B C13B H13B 119.0 . . ?

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
S1 C4 C5 C6 -179.1(5) . . . . ?
C1 C2 C3 C4 -0.8(10) . . . . ?
C1 C2 C3 C7 179.5(6) . . . . ?
C2 C1 C6 C5 -1.1(12) . . . . ?
C2 C1 C13A O1A 2(3) . . . . ?
C2 C3 C4 S1 179.6(5) . . . . ?
C2 C3 C4 C5 -0.5(10) . . . . ?
C2 C3 C7 C8 1.6(11) . . . . ?
C2 C3 C7 C12 -178.8(6) . . . . ?
C3 C4 C5 C6 1.0(11) . . . . ?
C3 C7 C8 C9 -179.1(6) . . . . ?
C3 C7 C12 S1 -1.7(7) . . . . ?
C3 C7 C12 C11 179.1(6) . . . . ?
C4 S1 C12 C7 1.1(5) . . . . ?
C4 S1 C12 C11 -179.7(6) . . . . ?
C4 C3 C7 C8 -178.2(6) . . . . ?
C4 C3 C7 C12 1.5(8) . . . . ?
C4 C5 C6 C1 -0.3(11) . . . . ?
C6 C1 C2 C3 1.6(11) . . . . ?
C6 C1 C13A O1A -179.5(15) . . . . ?
C7 C3 C4 S1 -0.6(7) . . . . ?
C7 C3 C4 C5 179.3(6) . . . . ?
C7 C8 C9 C10 0.7(11) . . . . ?
C7 C8 C9 Br2 -179.6(5) . . . . ?
C7 C8 C9 C13B -177.9(13) . . . . ?
C8 C7 C12 S1 178.0(5) . . . . ?
C8 C7 C12 C11 -1.2(10) . . . . ?
C8 C9 C10 C11 -2.9(11) . . . . ?
C8 C9 C13B O1B -3(3) . . . . ?
C9 C10 C11 C12 2.9(10) . . . . ?
C10 C9 C13B O1B 178(2) . . . . ?
C10 C11 C12 S1 180.0(5) . . . . ?
C10 C11 C12 C7 -0.9(10) . . . . ?
C12 S1 C4 C3 -0.3(5) . . . . ?
C12 S1 C4 C5 179.8(6) . . . . ?
C12 C7 C8 C9 1.3(10) . . . . ?
Br1 C1 C2 C3 -176.9(5) . . . . ?
Br1 C1 C6 C5 177.3(6) . . . . ?
C13A C1 C2 C3 179.9(12) . . . . ?
C13A C1 C6 C5 -179.7(10) . . . . ?
Br2 C9 C10 C11 177.4(6) . . . . ?
C13B C9 C10 C11 176.1(10) . . . . ?

_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_12345_tw
_database_code_depnum_ccdc_archive 'CCDC 2216489'
loop_
_audit_author_name
_audit_author_address
'guoyan li'
;University of  jinan
China
;
_audit_update_record             
;
2022-10-31 deposited with the CCDC.	2024-01-09 downloaded from the CCDC.
;
_audit_creation_date             2022-02-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H7 Br O S'
_chemical_formula_sum            'C13 H7 Br O S'
_chemical_formula_weight         291.16
_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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'

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

_cell_length_a                   39.011(3)
_cell_length_b                   3.8629(2)
_cell_length_c                   30.980(2)
_cell_angle_alpha                90
_cell_angle_beta                 113.013(2)
_cell_angle_gamma                90
_cell_volume                     4297.0(5)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    9933
_cell_measurement_temperature    170.0
_cell_measurement_theta_max      26.95
_cell_measurement_theta_min      2.14
_shelx_estimated_absorpt_T_max   0.796
_shelx_estimated_absorpt_T_min   0.250
_exptl_absorpt_coefficient_mu    3.991
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5166
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1539 before and 0.0646 after correction.
The Ratio of minimum to maximum transmission is 0.6930.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.800
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2304
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            7610
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.026
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         2.615
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6780
_reflns_number_total             7610
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.869
_refine_diff_density_min         -1.176
_refine_diff_density_rms         0.185
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.219
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     686
_refine_ls_number_reflns         7610
_refine_ls_number_restraints     148
_refine_ls_R_factor_all          0.1217
_refine_ls_R_factor_gt           0.1135
_refine_ls_restrained_S_all      1.212
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0304P)²+112.4195P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2496
_refine_ls_wR_factor_ref         0.2531
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.851(4)
 0.149(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 C3A-C01O = C4A-C00Z
 1.45 with sigma of 0.02
 O5-C4A = O6-C3A
 1.25 with sigma of 0.02
 C00H-C
 1.48 with sigma of 0.02
 C-O8
 1.25 with sigma of 0.02
 C1-C018
 1.48 with sigma of 0.02
 O2-C1
 1.25 with sigma of 0.02
 O1-C2 = O7-C5
 1.25 with sigma of 0.02
 C5-C00G = C2-C00N
 1.45 with sigma of 0.02
 C00G-C5
 1.48 with sigma of 0.02
 C5-O7
 1.25 with sigma of 0.02
 C00H-O8
 2.39 with sigma of 0.04
 C00G-O7
 2.39 with sigma of 0.04
4. Uiso/Uaniso restraints and constraints
C018 \\sim C1 \\sim O2: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
C00H \\sim C \\sim O8: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
C00H: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within
2A
C01P \\sim C2A \\sim O3: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
C01K \\sim C3 \\sim O4: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
C4A \\sim C00Z \\sim O5: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
C01O \\sim C3A \\sim O6: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
C2 \\sim O1 \\sim C00N: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
C00G \\sim C5 \\sim O7: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
Uanis(C00G) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(O7) \\sim Ueq: with sigma of
0.01 and sigma for terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 C00H, C, O8
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C00G, C5, O7
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
6. Others
 Fixed Sof: Br01(0.8) Br00(0.6) Br4(0.6) Br3(0.4) Br1(0.4) Br2(0.2) C1(0.8)
 H1(0.8) O1(0.8) O2(0.8) O3(0.6) O4(0.4) C2A(0.6) H2A(0.6) C3(0.4) H3(0.4)
 Br1A(0.2) Br(0.8) O5(0.4) O6(0.6) C3A(0.6) H3A(0.6) C4A(0.4) H4A(0.4) O7(0.2)
 C2(0.8) H2(0.8) C5(0.2) H5(0.2) O8(0.2) C(0.2) H(0.2)
7.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C00I(H00I), C00O(H00O), C00P(H00P), C00R(H00R), C00T(H00T),
 C00W(H00W), C00X(H00X), C00Y(H00Y), C010(H010), C011(H011), C014(H014),
 C016(H016), C017(H017), C019(H019), C01A(H01A), C01B(H01B), C01C(H01C),
 C01E(H01E), C01F(H01F), C01H(H01H), C01J(H01J), C01L(H01L), C01N(H01N),
 C01Q(H01Q), C2A(H2A), C3(H3), C3A(H3A), C4A(H4A), C2(H2), C5(H5), C(H)
;
_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
Br01 Br 0.04495(5) 0.9639(5) 0.03915(6) 0.0358(4) Uani 0.8 1 d . . P A 2
Br00 Br -0.04335(8) 0.5052(9) -0.21168(11) 0.0412(7) Uani 0.6 1 d . . P B 1
Br4 Br 0.54380(7) 0.5742(9) 0.33293(11) 0.0439(7) Uani 0.6 1 d . . P C 1
Br3 Br 0.34872(12) -0.3127(13) 0.13843(15) 0.0357(10) Uani 0.4 1 d . . P D 2
S006 S 0.19517(8) 0.5020(9) 0.20653(10) 0.0282(7) Uani 1 1 d . . . . .
S007 S 0.39365(8) 0.0829(9) 0.35263(11) 0.0301(7) Uani 1 1 d . . . . .
S008 S 0.10591(8) 0.0336(9) -0.04172(10) 0.0292(7) Uani 1 1 d . . . . .
S009 S 0.30699(8) 0.5873(10) 0.01381(11) 0.0326(7) Uani 1 1 d . . . . .
Br1 Br 0.1522(2) -0.412(2) -0.2087(2) 0.0431(15) Uani 0.4 1 d . . P E 2
Br2 Br 0.2328(5) 0.102(6) 0.0309(5) 0.066(4) Uani 0.2 1 d . . P F 1
C1 C 0.2608(9) 0.886(10) -0.1901(7) 0.038(5) Uani 0.8 1 d D U P G 1
H1 H 0.237590 0.997461 -0.206551 0.046 Uiso 0.8 1 calc R U P G 1
C00D C 0.1834(3) 0.432(3) 0.1177(4) 0.020(2) Uani 1 1 d . . . . .
C00E C 0.4051(3) 0.031(3) 0.2750(4) 0.023(2) Uani 1 1 d . . . . .
C00F C 0.1499(3) 0.589(3) 0.1184(4) 0.021(2) Uani 1 1 d . . . . .
C00G C 0.0890(3) 0.824(3) 0.0898(4) 0.031(3) Uani 1 1 d D U . . .
C00H C 0.4113(3) 0.201(3) 0.0004(4) 0.026(2) Uani 1 1 d D U . . .
C00I C 0.0917(3) 0.891(3) 0.1359(4) 0.031(3) Uani 1 1 d . . . . .
H00I H 0.071809 1.000154 0.141067 0.038 Uiso 1 1 calc R U . . .
C00K C 0.3165(3) 0.614(3) -0.0661(4) 0.024(2) Uani 1 1 d . . . . .
C00L C 0.0955(3) -0.036(3) -0.1297(4) 0.025(3) Uani 1 1 d . . . . .
C00M C 0.4374(3) 0.188(3) 0.3077(4) 0.025(2) Uani 1 1 d . . . . .
C00N C 0.2264(3) 0.205(3) 0.0858(4) 0.026(2) Uani 1 1 d D U . . .
C00O C 0.3070(3) 0.686(3) -0.1131(4) 0.025(2) Uani 1 1 d . . . . .
H00O H 0.323877 0.632636 -0.127470 0.030 Uiso 1 1 calc R U . . .
C00P C 0.4645(3) 0.394(4) 0.3897(4) 0.033(3) Uani 1 1 d . . . . .
H00P H 0.462863 0.424463 0.419235 0.040 Uiso 1 1 calc R U . . .
C00Q C 0.0636(3) 0.189(3) -0.0848(4) 0.027(3) Uani 1 1 d . . . . .
C00R C 0.4958(3) 0.499(3) 0.3821(5) 0.032(3) Uani 1 1 d . . . . .
H00R H 0.515608 0.610101 0.406695 0.039 Uiso 1 1 calc R U . . .
C00S C 0.3487(3) 0.423(4) 0.0126(4) 0.031(3) Uani 1 1 d . . . . .
C00T C 0.1626(3) -0.375(4) -0.1144(4) 0.033(3) Uani 1 1 d . . . . .
H00T H 0.185202 -0.491497 -0.109582 0.039 Uiso 1 1 calc R U . . .
C00U C 0.3506(3) 0.467(3) -0.0316(4) 0.026(3) Uani 1 1 d . . . . .
C00V C 0.4354(3) 0.241(3) 0.3516(4) 0.027(3) Uani 1 1 d . . . . .
C00W C 0.4699(3) 0.296(4) 0.3016(4) 0.031(3) Uani 1 1 d . . . . .
H00W H 0.472138 0.266009 0.272371 0.037 Uiso 1 1 calc R U . . .
C00X C 0.2574(3) 0.860(4) -0.0701(5) 0.033(3) Uani 1 1 d . . . . .
H00X H 0.240793 0.918017 -0.055595 0.040 Uiso 1 1 calc R U . . .
C00Y C 0.0301(3) 0.231(3) -0.1685(4) 0.030(3) Uani 1 1 d . . . . .
H00Y H 0.028334 0.199215 -0.199737 0.036 Uiso 1 1 calc R U . . .
C00Z C 0.4986(3) 0.447(4) 0.3398(5) 0.032(3) Uani 1 1 d D U . . .
C010 C 0.1916(3) 0.353(3) 0.0783(4) 0.028(3) Uani 1 1 d . . . . .
H010 H 0.174005 0.399217 0.047414 0.033 Uiso 1 1 calc R U . . .
C011 C 0.3821(3) 0.347(3) -0.0375(4) 0.022(2) Uani 1 1 d . . . . .
H011 H 0.383708 0.363113 -0.067265 0.026 Uiso 1 1 calc R U . . .
C012 C 0.1530(3) 0.642(3) 0.1651(4) 0.024(2) Uani 1 1 d . . . . .
C013 C 0.1206(3) -0.113(4) -0.0848(4) 0.030(3) Uani 1 1 d . . . . .
C014 C 0.2447(3) 0.213(3) 0.1706(4) 0.030(3) Uani 1 1 d . . . . .
H014 H 0.261606 0.155213 0.201358 0.036 Uiso 1 1 calc R U . . .
C015 C 0.2912(3) 0.701(3) -0.0453(4) 0.028(3) Uani 1 1 d . . . . .
C016 C 0.1173(3) 0.680(4) 0.0805(4) 0.027(3) Uani 1 1 d . . . . .
H016 H 0.115001 0.643359 0.049148 0.033 Uiso 1 1 calc R U . . .
C017 C 0.2487(3) 0.932(4) -0.1172(4) 0.033(3) Uani 1 1 d . . . . .
H017 H 0.226129 1.048925 -0.134856 0.040 Uiso 1 1 calc R U . . .
C018 C 0.2727(3) 0.836(4) -0.1392(4) 0.032(3) Uani 1 1 d D U . . .
C019 C 0.1553(3) -0.276(4) -0.0759(5) 0.034(3) Uani 1 1 d . . . . .
H019 H 0.172742 -0.316207 -0.044798 0.041 Uiso 1 1 calc R U . . .
C01A C 0.3443(3) -0.206(3) 0.2682(5) 0.032(3) Uani 1 1 d . . . . .
H01A H 0.327035 -0.261969 0.281825 0.039 Uiso 1 1 calc R U . . .
C01B C 0.0041(3) 0.452(4) -0.1138(4) 0.034(3) Uani 1 1 d . . . . .
H01B H -0.015786 0.563839 -0.108874 0.041 Uiso 1 1 calc R U . . .
C01C C 0.1237(3) 0.794(3) 0.1731(4) 0.031(3) Uani 1 1 d . . . . .
H01C H 0.125687 0.831781 0.204322 0.037 Uiso 1 1 calc R U . . .
C01D C 0.3782(3) -0.039(3) 0.2942(4) 0.025(2) Uani 1 1 d . . . . .
C01E C 0.2530(3) 0.141(4) 0.1316(4) 0.029(3) Uani 1 1 d . . . . .
H01E H 0.276644 0.048459 0.135872 0.034 Uiso 1 1 calc R U . . .
C01F C 0.3777(4) 0.281(4) 0.0508(4) 0.039(3) Uani 1 1 d . . . . .
H01F H 0.375962 0.257819 0.080456 0.047 Uiso 1 1 calc R U . . .
C01G C 0.2105(3) 0.374(3) 0.1626(4) 0.024(2) Uani 1 1 d . . . . .
C01H C 0.1038(3) -0.132(3) -0.1682(4) 0.030(3) Uani 1 1 d . . . . .
H01H H 0.086906 -0.079786 -0.199190 0.036 Uiso 1 1 calc R U . . .
C01I C 0.0619(3) 0.124(4) -0.1303(4) 0.032(3) Uani 1 1 d . . . . .
C01J C 0.4097(3) 0.172(4) 0.0440(4) 0.031(3) Uani 1 1 d . . . . .
H01J H 0.430184 0.077827 0.069477 0.037 Uiso 1 1 calc R U . . .
C01K C 0.0018(3) 0.383(3) -0.1601(4) 0.029(3) Uani 1 1 d . U . . .
C01L C 0.3371(3) -0.288(3) 0.2213(4) 0.032(3) Uani 1 1 d . . . . .
H01L H 0.314339 -0.398193 0.202715 0.038 Uiso 1 1 calc R U . . .
C01N C 0.3959(3) -0.046(4) 0.2278(4) 0.032(3) Uani 1 1 d . . . . .
H01N H 0.412561 0.014215 0.213287 0.038 Uiso 1 1 calc R U . . .
C01O C 0.3624(4) -0.211(4) 0.2018(4) 0.038(3) Uani 1 1 d D U . . .
C01P C 0.1372(3) -0.306(4) -0.1605(5) 0.034(3) Uani 1 1 d . U . . .
C01Q C 0.0357(3) 0.354(4) -0.0766(4) 0.032(3) Uani 1 1 d . . . . .
H01Q H 0.038218 0.399539 -0.045339 0.038 Uiso 1 1 calc R U . . .
O1 O 0.2159(4) 0.177(5) 0.0040(5) 0.057(4) Uani 0.8 1 d D U P F 2
O2 O 0.2794(3) 0.791(4) -0.2132(4) 0.050(3) Uani 0.8 1 d D U P G 1
O3 O 0.1698(5) -0.585(6) -0.2008(6) 0.051(5) Uani 0.6 1 d . U P E 1
O4 O -0.0389(10) 0.483(10) -0.2349(13) 0.073(9) Uani 0.4 1 d . U P B 2
C2A C 0.1457(12) -0.453(14) -0.2028(16) 0.038(6) Uani 0.6 1 d . U P E 1
H2A H 0.126992 -0.419007 -0.233299 0.045 Uiso 0.6 1 calc R U P E 1
C3 C -0.0333(13) 0.534(13) -0.1948(17) 0.039(6) Uani 0.4 1 d . U P B 2
H3 H -0.050115 0.661947 -0.185508 0.046 Uiso 0.4 1 calc R U P B 2
Br1A Br 0.2626(5) 0.953(5) -0.1984(5) 0.069(5) Uani 0.2 1 d . . P G 2
Br Br 0.45450(5) 0.0538(5) -0.00750(7) 0.0362(4) Uani 0.8 1 d . . P H 1
O5 O 0.5378(8) 0.572(9) 0.3006(12) 0.067(7) Uani 0.4 1 d D U P C 2
O6 O 0.3353(7) -0.487(8) 0.1306(7) 0.073(6) Uani 0.6 1 d D U P D 1
C3A C 0.3566(11) -0.258(10) 0.1522(8) 0.047(6) Uani 0.6 1 d D U P D 1
H3A H 0.368884 -0.115603 0.137651 0.057 Uiso 0.6 1 calc R U P D 1
C4A C 0.5317(9) 0.600(12) 0.3371(13) 0.038(6) Uani 0.4 1 d D U P C 2
H4A H 0.548774 0.722226 0.363303 0.046 Uiso 0.4 1 calc R U P C 2
O7 O 0.0353(12) 1.169(14) 0.0443(18) 0.053(9) Uani 0.2 1 d D U P A 1
C2 C 0.2364(9) 0.120(11) 0.0465(6) 0.036(5) Uani 0.8 1 d D U P F 2
H2 H 0.259958 0.014532 0.053146 0.043 Uiso 0.8 1 calc R U P F 2
C5 C 0.0545(15) 0.903(17) 0.0494(19) 0.034(6) Uani 0.2 1 d D U P A 1
H5 H 0.046104 0.735943 0.024872 0.041 Uiso 0.2 1 calc R U P A 1
O8 O 0.4573(12) 0.020(14) -0.0280(16) 0.036(8) Uani 0.2 1 d D U P H 2
C C 0.4479(11) 0.054(19) 0.0059(17) 0.028(5) Uani 0.2 1 d D U P H 2
H H 0.464620 -0.016665 0.036227 0.033 Uiso 0.2 1 calc R U P H 2


_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
Br01 C00G 1.896(12) . ?
Br00 C01K 1.917(12) . ?
Br4 C00Z 1.923(12) . ?
Br3 C01O 1.864(13) . ?
S006 C012 1.731(11) . ?
S006 C01G 1.760(11) . ?
S007 C00V 1.752(12) . ?
S007 C01D 1.734(12) . ?
S008 C00Q 1.774(11) . ?
S008 C013 1.740(12) . ?
S009 C00S 1.760(13) . ?
S009 C015 1.744(12) . ?
Br1 C01P 1.851(14) . ?
Br2 C00N 1.856(18) . ?
C1 H1 0.9500 . ?
C1 C018 1.472(18) . ?
C1 O2 1.256(19) . ?
C00D C00F 1.448(14) . ?
C00D C010 1.413(15) . ?
C00D C01G 1.397(15) . ?
C00E C00M 1.409(16) . ?
C00E C01D 1.420(15) . ?
C00E C01N 1.395(17) . ?
C00F C012 1.416(14) . ?
C00F C016 1.396(16) . ?
C00G C00I 1.413(17) . ?
C00G C016 1.365(17) . ?
C00G C5 1.467(15) . ?
C00H C011 1.395(16) . ?
C00H C01J 1.382(17) . ?
C00H Br 1.883(12) . ?
C00H C 1.48(2) . ?
C00I H00I 0.9500 . ?
C00I C01C 1.379(17) . ?
C00K C00O 1.382(15) . ?
C00K C00U 1.455(16) . ?
C00K C015 1.414(15) . ?
C00L C013 1.384(17) . ?
C00L C01H 1.402(16) . ?
C00L C01I 1.443(16) . ?
C00M C00V 1.409(16) . ?
C00M C00W 1.413(16) . ?
C00N C010 1.409(15) . ?
C00N C01E 1.414(16) . ?
C00N C2 1.455(18) . ?
C00O H00O 0.9500 . ?
C00O C018 1.392(16) . ?
C00P H00P 0.9500 . ?
C00P C00R 1.389(18) . ?
C00P C00V 1.408(18) . ?
C00Q C01I 1.409(17) . ?
C00Q C01Q 1.366(18) . ?
C00R H00R 0.9500 . ?
C00R C00Z 1.371(18) . ?
C00S C00U 1.412(16) . ?
C00S C01F 1.391(18) . ?
C00T H00T 0.9500 . ?
C00T C019 1.383(18) . ?
C00T C01P 1.410(17) . ?
C00U C011 1.390(15) . ?
C00W H00W 0.9500 . ?
C00W C00Z 1.400(17) . ?
C00X H00X 0.9500 . ?
C00X C015 1.385(17) . ?
C00X C017 1.390(18) . ?
C00Y H00Y 0.9500 . ?
C00Y C01I 1.402(17) . ?
C00Y C01K 1.363(17) . ?
C00Z C4A 1.453(19) . ?
C010 H010 0.9500 . ?
C011 H011 0.9500 . ?
C012 C01C 1.394(17) . ?
C013 C019 1.418(17) . ?
C014 H014 0.9500 . ?
C014 C01E 1.393(16) . ?
C014 C01G 1.403(17) . ?
C016 H016 0.9500 . ?
C017 H017 0.9500 . ?
C017 C018 1.406(17) . ?
C018 Br1A 1.777(18) . ?
C019 H019 0.9500 . ?
C01A H01A 0.9500 . ?
C01A C01D 1.409(17) . ?
C01A C01L 1.402(18) . ?
C01B H01B 0.9500 . ?
C01B C01K 1.427(18) . ?
C01B C01Q 1.374(18) . ?
C01C H01C 0.9500 . ?
C01E H01E 0.9500 . ?
C01F H01F 0.9500 . ?
C01F C01J 1.409(18) . ?
C01H H01H 0.9500 . ?
C01H C01P 1.401(17) . ?
C01J H01J 0.9500 . ?
C01K C3 1.49(5) . ?
C01L H01L 0.9500 . ?
C01L C01O 1.376(18) . ?
C01N H01N 0.9500 . ?
C01N C01O 1.394(18) . ?
C01O C3A 1.475(19) . ?
C01P C2A 1.58(5) . ?
C01Q H01Q 0.9500 . ?
O1 C2 1.264(18) . ?
O3 C2A 1.05(6) . ?
O4 C3 1.19(6) . ?
C2A H2A 0.9500 . ?
C3 H3 0.9500 . ?
O5 C4A 1.25(2) . ?
O6 C3A 1.220(19) . ?
C3A H3A 0.9500 . ?
C4A H4A 0.9500 . ?
O7 C5 1.246(15) . ?
C2 H2 0.9500 . ?
C5 H5 0.9500 . ?
O8 C 1.25(2) . ?
C H 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
C012 S006 C01G 91.5(5) . . ?
C01D S007 C00V 91.2(6) . . ?
C013 S008 C00Q 91.3(6) . . ?
C015 S009 C00S 91.0(6) . . ?
C018 C1 H1 118.0 . . ?
O2 C1 H1 118.0 . . ?
O2 C1 C018 124(2) . . ?
C010 C00D C00F 127.9(10) . . ?
C01G C00D C00F 113.0(10) . . ?
C01G C00D C010 119.0(10) . . ?
C00M C00E C01D 112.3(10) . . ?
C01N C00E C00M 129.6(11) . . ?
C01N C00E C01D 118.0(10) . . ?
C012 C00F C00D 110.9(10) . . ?
C016 C00F C00D 128.4(10) . . ?
C016 C00F C012 120.6(10) . . ?
C00I C00G Br01 118.0(9) . . ?
C00I C00G C5 120(3) . . ?
C016 C00G Br01 119.2(9) . . ?
C016 C00G C00I 122.7(11) . . ?
C016 C00G C5 117(3) . . ?
C011 C00H Br 119.3(9) . . ?
C011 C00H C 133(2) . . ?
C01J C00H C011 121.4(11) . . ?
C01J C00H Br 119.2(9) . . ?
C01J C00H C 105(2) . . ?
C00G C00I H00I 120.6 . . ?
C01C C00I C00G 118.8(11) . . ?
C01C C00I H00I 120.6 . . ?
C00O C00K C00U 130.0(10) . . ?
C00O C00K C015 119.0(11) . . ?
C015 C00K C00U 111.0(10) . . ?
C013 C00L C01H 119.4(10) . . ?
C013 C00L C01I 112.8(10) . . ?
C01H C00L C01I 127.7(11) . . ?
C00E C00M C00V 112.7(10) . . ?
C00E C00M C00W 128.7(11) . . ?
C00V C00M C00W 118.6(11) . . ?
C010 C00N Br2 113.7(9) . . ?
C010 C00N C01E 121.2(10) . . ?
C010 C00N C2 120.7(14) . . ?
C01E C00N Br2 125.1(10) . . ?
C01E C00N C2 118.1(13) . . ?
C00K C00O H00O 120.1 . . ?
C00K C00O C018 119.8(11) . . ?
C018 C00O H00O 120.1 . . ?
C00R C00P H00P 121.5 . . ?
C00R C00P C00V 117.0(11) . . ?
C00V C00P H00P 121.5 . . ?
C01I C00Q S008 111.0(9) . . ?
C01Q C00Q S008 126.3(10) . . ?
C01Q C00Q C01I 122.8(11) . . ?
C00P C00R H00R 119.3 . . ?
C00Z C00R C00P 121.4(11) . . ?
C00Z C00R H00R 119.3 . . ?
C00U C00S S009 112.2(9) . . ?
C01F C00S S009 125.1(10) . . ?
C01F C00S C00U 122.7(11) . . ?
C019 C00T H00T 119.2 . . ?
C019 C00T C01P 121.5(12) . . ?
C01P C00T H00T 119.2 . . ?
C00S C00U C00K 112.2(10) . . ?
C011 C00U C00K 129.4(10) . . ?
C011 C00U C00S 118.2(11) . . ?
C00M C00V S007 111.7(9) . . ?
C00P C00V S007 125.7(9) . . ?
C00P C00V C00M 122.6(11) . . ?
C00M C00W H00W 121.0 . . ?
C00Z C00W C00M 118.1(11) . . ?
C00Z C00W H00W 121.0 . . ?
C015 C00X H00X 121.3 . . ?
C015 C00X C017 117.5(11) . . ?
C017 C00X H00X 121.3 . . ?
C01I C00Y H00Y 120.6 . . ?
C01K C00Y H00Y 120.6 . . ?
C01K C00Y C01I 118.8(12) . . ?
C00R C00Z Br4 119.2(9) . . ?
C00R C00Z C00W 122.3(11) . . ?
C00R C00Z C4A 113.5(17) . . ?
C00W C00Z Br4 118.5(9) . . ?
C00W C00Z C4A 123.8(18) . . ?
C00D C010 H010 120.8 . . ?
C00N C010 C00D 118.4(10) . . ?
C00N C010 H010 120.8 . . ?
C00H C011 H011 120.1 . . ?
C00U C011 C00H 119.8(11) . . ?
C00U C011 H011 120.1 . . ?
C00F C012 S006 112.9(8) . . ?
C01C C012 S006 127.4(9) . . ?
C01C C012 C00F 119.6(10) . . ?
C00L C013 S008 112.6(9) . . ?
C00L C013 C019 122.5(11) . . ?
C019 C013 S008 124.8(10) . . ?
C01E C014 H014 121.3 . . ?
C01E C014 C01G 117.5(11) . . ?
C01G C014 H014 121.3 . . ?
C00K C015 S009 113.3(9) . . ?
C00X C015 S009 124.3(9) . . ?
C00X C015 C00K 122.3(11) . . ?
C00F C016 H016 121.0 . . ?
C00G C016 C00F 118.0(11) . . ?
C00G C016 H016 121.0 . . ?
C00X C017 H017 119.3 . . ?
C00X C017 C018 121.3(11) . . ?
C018 C017 H017 119.3 . . ?
C00O C018 C1 120.5(15) . . ?
C00O C018 C017 119.9(11) . . ?
C00O C018 Br1A 118.8(11) . . ?
C017 C018 C1 119.6(13) . . ?
C017 C018 Br1A 120.8(11) . . ?
C00T C019 C013 117.2(12) . . ?
C00T C019 H019 121.4 . . ?
C013 C019 H019 121.4 . . ?
C01D C01A H01A 121.3 . . ?
C01L C01A H01A 121.3 . . ?
C01L C01A C01D 117.3(11) . . ?
C01K C01B H01B 120.8 . . ?
C01Q C01B H01B 120.8 . . ?
C01Q C01B C01K 118.4(12) . . ?
C00I C01C C012 120.1(11) . . ?
C00I C01C H01C 119.9 . . ?
C012 C01C H01C 119.9 . . ?
C00E C01D S007 112.0(9) . . ?
C01A C01D S007 125.9(9) . . ?
C01A C01D C00E 122.0(11) . . ?
C00N C01E H01E 119.7 . . ?
C014 C01E C00N 120.6(11) . . ?
C014 C01E H01E 119.7 . . ?
C00S C01F H01F 121.2 . . ?
C00S C01F C01J 117.6(12) . . ?
C01J C01F H01F 121.2 . . ?
C00D C01G S006 111.6(8) . . ?
C00D C01G C014 123.1(10) . . ?
C014 C01G S006 125.2(9) . . ?
C00L C01H H01H 120.3 . . ?
C01P C01H C00L 119.3(11) . . ?
C01P C01H H01H 120.3 . . ?
C00Q C01I C00L 112.1(10) . . ?
C00Y C01I C00L 129.6(11) . . ?
C00Y C01I C00Q 118.2(12) . . ?
C00H C01J C01F 120.3(11) . . ?
C00H C01J H01J 119.8 . . ?
C01F C01J H01J 119.8 . . ?
C00Y C01K Br00 119.7(10) . . ?
C00Y C01K C01B 122.4(11) . . ?
C00Y C01K C3 128(2) . . ?
C01B C01K Br00 117.9(9) . . ?
C01B C01K C3 109(2) . . ?
C01A C01L H01L 119.4 . . ?
C01O C01L C01A 121.2(11) . . ?
C01O C01L H01L 119.4 . . ?
C00E C01N H01N 120.0 . . ?
C01O C01N C00E 120.1(11) . . ?
C01O C01N H01N 120.0 . . ?
C01L C01O Br3 117.3(9) . . ?
C01L C01O C01N 121.2(12) . . ?
C01L C01O C3A 126.0(18) . . ?
C01N C01O Br3 121.4(10) . . ?
C01N C01O C3A 112.6(17) . . ?
C00T C01P Br1 117.3(9) . . ?
C00T C01P C2A 119(2) . . ?
C01H C01P Br1 122.4(10) . . ?
C01H C01P C00T 120.0(12) . . ?
C01H C01P C2A 121(2) . . ?
C00Q C01Q C01B 119.4(12) . . ?
C00Q C01Q H01Q 120.3 . . ?
C01B C01Q H01Q 120.3 . . ?
C01P C2A H2A 116.5 . . ?
O3 C2A C01P 127(4) . . ?
O3 C2A H2A 116.5 . . ?
C01K C3 H3 122.3 . . ?
O4 C3 C01K 115(4) . . ?
O4 C3 H3 122.3 . . ?
C01O C3A H3A 121.5 . . ?
O6 C3A C01O 117(2) . . ?
O6 C3A H3A 121.5 . . ?
C00Z C4A H4A 119.8 . . ?
O5 C4A C00Z 120(3) . . ?
O5 C4A H4A 119.8 . . ?
C00N C2 H2 117.8 . . ?
O1 C2 C00N 124(2) . . ?
O1 C2 H2 117.8 . . ?
C00G C5 H5 117.2 . . ?
O7 C5 C00G 126(3) . . ?
O7 C5 H5 117.2 . . ?
C00H C H 119.0 . . ?
O8 C C00H 122(3) . . ?
O8 C H 119.0 . . ?

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
Br01 C00G C00I C01C -179.3(10) . . . . ?
Br01 C00G C016 C00F 178.2(9) . . . . ?
S006 C012 C01C C00I -179.8(10) . . . . ?
S008 C00Q C01I C00L -2.5(14) . . . . ?
S008 C00Q C01I C00Y 179.9(10) . . . . ?
S008 C00Q C01Q C01B -178.5(10) . . . . ?
S008 C013 C019 C00T -179.7(11) . . . . ?
S009 C00S C00U C00K -4.1(14) . . . . ?
S009 C00S C00U C011 -179.6(9) . . . . ?
S009 C00S C01F C01J -178.0(11) . . . . ?
Br2 C00N C010 C00D 178.1(12) . . . . ?
Br2 C00N C01E C014 -176.9(13) . . . . ?
C00D C00F C012 S006 -0.5(13) . . . . ?
C00D C00F C012 C01C 179.4(11) . . . . ?
C00D C00F C016 C00G 179.5(12) . . . . ?
C00E C00M C00V S007 1.8(14) . . . . ?
C00E C00M C00V C00P 179.9(12) . . . . ?
C00E C00M C00W C00Z -179.9(12) . . . . ?
C00E C01N C01O Br3 179.1(10) . . . . ?
C00E C01N C01O C01L 3(2) . . . . ?
C00E C01N C01O C3A 177(2) . . . . ?
C00F C00D C010 C00N 178.9(12) . . . . ?
C00F C00D C01G S006 1.2(13) . . . . ?
C00F C00D C01G C014 177.7(11) . . . . ?
C00F C012 C01C C00I 0.4(19) . . . . ?
C00G C00I C01C C012 2(2) . . . . ?
C00I C00G C016 C00F 2(2) . . . . ?
C00I C00G C5 O7 43(11) . . . . ?
C00K C00O C018 C1 -175(2) . . . . ?
C00K C00O C018 C017 3.7(19) . . . . ?
C00K C00O C018 Br1A 175.5(13) . . . . ?
C00K C00U C011 C00H -177.3(12) . . . . ?
C00L C013 C019 C00T -3(2) . . . . ?
C00L C01H C01P Br1 -174.9(10) . . . . ?
C00L C01H C01P C00T -2(2) . . . . ?
C00L C01H C01P C2A 174(2) . . . . ?
C00M C00E C01D S007 -1.3(13) . . . . ?
C00M C00E C01D C01A -177.7(12) . . . . ?
C00M C00E C01N C01O 178.6(13) . . . . ?
C00M C00W C00Z Br4 177.1(10) . . . . ?
C00M C00W C00Z C00R -1(2) . . . . ?
C00M C00W C00Z C4A -174(3) . . . . ?
C00O C00K C00U C00S -177.8(13) . . . . ?
C00O C00K C00U C011 -3(2) . . . . ?
C00O C00K C015 S009 178.9(10) . . . . ?
C00O C00K C015 C00X -0.9(19) . . . . ?
C00P C00R C00Z Br4 -176.4(10) . . . . ?
C00P C00R C00Z C00W 2(2) . . . . ?
C00P C00R C00Z C4A 175(2) . . . . ?
C00Q S008 C013 C00L 2.3(11) . . . . ?
C00Q S008 C013 C019 179.1(13) . . . . ?
C00R C00P C00V S007 179.0(10) . . . . ?
C00R C00P C00V C00M 1(2) . . . . ?
C00R C00Z C4A O5 -180(4) . . . . ?
C00S S009 C015 C00K 0.8(10) . . . . ?
C00S S009 C015 C00X -179.4(12) . . . . ?
C00S C00U C011 C00H -2.8(18) . . . . ?
C00S C01F C01J C00H -1(2) . . . . ?
C00T C01P C2A O3 -5(6) . . . . ?
C00U C00K C00O C018 -178.5(13) . . . . ?
C00U C00K C015 S009 -3.3(14) . . . . ?
C00U C00K C015 C00X 176.9(12) . . . . ?
C00U C00S C01F C01J -1(2) . . . . ?
C00V S007 C01D C00E 1.9(10) . . . . ?
C00V S007 C01D C01A 178.2(12) . . . . ?
C00V C00M C00W C00Z 0.6(19) . . . . ?
C00V C00P C00R C00Z -2(2) . . . . ?
C00W C00M C00V S007 -178.7(10) . . . . ?
C00W C00M C00V C00P -0.5(19) . . . . ?
C00W C00Z C4A O5 -7(6) . . . . ?
C00X C017 C018 C1 174(2) . . . . ?
C00X C017 C018 C00O -4(2) . . . . ?
C00X C017 C018 Br1A -176.0(13) . . . . ?
C00Y C01K C3 O4 9(6) . . . . ?
C010 C00D C00F C012 -177.0(12) . . . . ?
C010 C00D C00F C016 4(2) . . . . ?
C010 C00D C01G S006 178.1(9) . . . . ?
C010 C00D C01G C014 -5.5(18) . . . . ?
C010 C00N C01E C014 2(2) . . . . ?
C010 C00N C2 O1 2(5) . . . . ?
C011 C00H C01J C01F 2(2) . . . . ?
C011 C00H C O8 -5(11) . . . . ?
C012 S006 C01G C00D -1.3(10) . . . . ?
C012 S006 C01G C014 -177.6(11) . . . . ?
C012 C00F C016 C00G 0.5(19) . . . . ?
C013 S008 C00Q C01I 0.2(10) . . . . ?
C013 S008 C00Q C01Q -179.2(12) . . . . ?
C013 C00L C01H C01P 0.4(19) . . . . ?
C013 C00L C01I C00Q 4.4(16) . . . . ?
C013 C00L C01I C00Y -178.5(13) . . . . ?
C015 S009 C00S C00U 1.9(11) . . . . ?
C015 S009 C00S C01F 179.1(13) . . . . ?
C015 C00K C00O C018 -1.2(19) . . . . ?
C015 C00K C00U C00S 4.7(16) . . . . ?
C015 C00K C00U C011 179.5(13) . . . . ?
C015 C00X C017 C018 2(2) . . . . ?
C016 C00F C012 S006 178.6(10) . . . . ?
C016 C00F C012 C01C -1.5(18) . . . . ?
C016 C00G C00I C01C -3(2) . . . . ?
C016 C00G C5 O7 -139(8) . . . . ?
C017 C00X C015 S009 -179.5(11) . . . . ?
C017 C00X C015 C00K 0(2) . . . . ?
C019 C00T C01P Br1 174.0(11) . . . . ?
C019 C00T C01P C01H 1(2) . . . . ?
C019 C00T C01P C2A -175(2) . . . . ?
C01A C01L C01O Br3 -177.2(10) . . . . ?
C01A C01L C01O C01N -1(2) . . . . ?
C01A C01L C01O C3A -175(2) . . . . ?
C01B C01K C3 O4 -178(4) . . . . ?
C01D S007 C00V C00M -2.1(10) . . . . ?
C01D S007 C00V C00P 179.8(12) . . . . ?
C01D C00E C00M C00V -0.3(15) . . . . ?
C01D C00E C00M C00W -179.8(13) . . . . ?
C01D C00E C01N C01O -4.9(19) . . . . ?
C01D C01A C01L C01O 1(2) . . . . ?
C01E C00N C010 C00D -1.0(19) . . . . ?
C01E C00N C2 O1 -177(3) . . . . ?
C01E C014 C01G S006 -177.5(10) . . . . ?
C01E C014 C01G C00D 6.5(18) . . . . ?
C01F C00S C00U C00K 178.7(13) . . . . ?
C01F C00S C00U C011 3(2) . . . . ?
C01G S006 C012 C00F 1.0(10) . . . . ?
C01G S006 C012 C01C -178.8(12) . . . . ?
C01G C00D C00F C012 -0.4(14) . . . . ?
C01G C00D C00F C016 -179.5(12) . . . . ?
C01G C00D C010 C00N 2.6(18) . . . . ?
C01G C014 C01E C00N -4.7(19) . . . . ?
C01H C00L C013 S008 179.0(10) . . . . ?
C01H C00L C013 C019 2(2) . . . . ?
C01H C00L C01I C00Q -179.2(12) . . . . ?
C01H C00L C01I C00Y -2(2) . . . . ?
C01H C01P C2A O3 179(4) . . . . ?
C01I C00L C013 S008 -4.2(15) . . . . ?
C01I C00L C013 C019 178.9(12) . . . . ?
C01I C00L C01H C01P -175.8(13) . . . . ?
C01I C00Q C01Q C01B 2(2) . . . . ?
C01I C00Y C01K Br00 -176.1(10) . . . . ?
C01I C00Y C01K C01B 3.3(19) . . . . ?
C01I C00Y C01K C3 176(3) . . . . ?
C01J C00H C011 C00U 0.4(18) . . . . ?
C01J C00H C O8 175(7) . . . . ?
C01K C00Y C01I C00L -179.1(13) . . . . ?
C01K C00Y C01I C00Q -2.1(18) . . . . ?
C01K C01B C01Q C00Q -1(2) . . . . ?
C01L C01A C01D S007 -179.1(10) . . . . ?
C01L C01A C01D C00E -3.2(19) . . . . ?
C01L C01O C3A O6 -28(5) . . . . ?
C01N C00E C00M C00V 176.3(13) . . . . ?
C01N C00E C00M C00W -3(2) . . . . ?
C01N C00E C01D S007 -178.4(10) . . . . ?
C01N C00E C01D C01A 5.2(18) . . . . ?
C01N C01O C3A O6 157(3) . . . . ?
C01P C00T C019 C013 2(2) . . . . ?
C01Q C00Q C01I C00L 176.9(12) . . . . ?
C01Q C00Q C01I C00Y -0.6(19) . . . . ?
C01Q C01B C01K Br00 177.6(10) . . . . ?
C01Q C01B C01K C00Y -2(2) . . . . ?
C01Q C01B C01K C3 -176(2) . . . . ?
O2 C1 C018 C00O 2(5) . . . . ?
O2 C1 C018 C017 -176(3) . . . . ?
Br C00H C011 C00U -177.8(9) . . . . ?
Br C00H C01J C01F 179.9(11) . . . . ?
C2 C00N C010 C00D -180(2) . . . . ?
C2 C00N C01E C014 -179(2) . . . . ?
C5 C00G C00I C01C 176(4) . . . . ?
C5 C00G C016 C00F -177(4) . . . . ?
C C00H C011 C00U -180(4) . . . . ?
C C00H C01J C01F -178(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.851(4)
2 0.149(4)

####################################################################### 
# 
# 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_mo_220605_LYX_WHJ_1N1_B
_database_code_depnum_ccdc_archive 'CCDC 2209689'
loop_
_audit_author_name
_audit_author_address
'guoyan li'
;University of Jinan
China
;
_audit_update_record             
;
2022-09-27 deposited with the CCDC.	2024-01-09 downloaded from the CCDC.
;
_audit_creation_date             2022-06-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_chemical_formula_moiety         'C15 H12 Br N O'
_chemical_formula_sum            'C15 H12 Br N O'
_chemical_formula_weight         302.172
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95570 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           ' P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_symmetry_Int_Tables_number      19
_cell_length_a                   4.3021(2)
_cell_length_b                   11.0405(6)
_cell_length_c                   26.4287(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1255.29(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6322
_cell_measurement_temperature    170.0
_cell_measurement_theta_max      26.28
_cell_measurement_theta_min      2.96
_exptl_absorpt_coefficient_mu    3.260
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5395
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1485 before and 0.0921 after correction.
The Ratio of minimum to maximum transmission is 0.7237.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_description       block
_exptl_crystal_F_000             607.522
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_diffrn_reflns_av_R_equivalents  0.0926
_diffrn_reflns_av_unetI/netI     0.0523
_diffrn_reflns_Laue_measured_fraction_full 0.9933
_diffrn_reflns_Laue_measured_fraction_max 0.9933
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            23513
_diffrn_reflns_point_group_measured_fraction_full 0.9946
_diffrn_reflns_point_group_measured_fraction_max 0.9946
_diffrn_reflns_theta_full        25.0195
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.40
_diffrn_ambient_temperature      170.00
_diffrn_detector_area_resol_mean 5.6
_diffrn_detector_type            'Bruker SMART CCD 6000 area detector'
_diffrn_measured_fraction_theta_full 0.9933
_diffrn_measured_fraction_theta_max 0.9933
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.997
_reflns_limit_h_max              5
_reflns_limit_h_min              -5
_reflns_limit_k_max              13
_reflns_limit_k_min              -12
_reflns_limit_l_max              31
_reflns_limit_l_min              -30
_reflns_number_gt                2108
_reflns_number_total             2201
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.6332
_refine_diff_density_min         -1.1110
_refine_diff_density_rms         0.1677
_refine_ls_abs_structure_details 
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   0.128(10)
_refine_ls_d_res_high            0.8403
_refine_ls_d_res_low             8.4725
_refine_ls_goodness_of_fit_ref   1.1923
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    26
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2201
_refine_ls_number_restraints     27
_refine_ls_R_factor_all          0.0955
_refine_ls_R_factor_gt           0.0929
_refine_ls_restrained_S_all      1.1845
_refine_ls_shift/su_max          0.0596
_refine_ls_shift/su_mean         0.0074
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0000P)²+15.2568P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2174
_refine_ls_wR_factor_ref         0.2187
_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. Restrained distances
 C15-O1
 1.2 with sigma of 0.02
 C11-C15
 1.4 with sigma of 0.02
 C15A-O1A
 1.2 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C2 \\sim C11 \\sim O1 \\sim C15 \\sim O1A \\sim C15A: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02 within 2A
4. Others
 Sof(Br1A)=Sof(O1A)=Sof(C15A)=Sof(H15A)=1-FVAR(1)
 Sof(Br1)=Sof(O1)=Sof(C15)=Sof(H15)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C13(H13a,H13b)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C3(H3), C10(H10), C9(H9), C12(H12), C15(H15), C15A(H15A)
5.c Fitted hexagon refined as free rotating group:
 C2(C1,C6,C5,C4,C3), C11(C10,C9,C8,C7,C12)
5.d Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c)
;
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
_atom_site_refinement_flags_adp
_atom_site_disorder_group
N1 N 0.250(2) 0.4947(7) 0.6252(3) 0.036(2) Uani 1.000000 . . .
C2 C 0.7946(16) 0.4505(6) 0.7526(2) 0.036(3) Uani 1.000000 . U .
C1 C 0.7273(16) 0.3567(4) 0.7193(2) 0.034(2) Uani 1.000000 G . .
H1 H 0.8058(16) 0.2776(4) 0.7256(2) 0.041(3) Uiso 1.000000 R . .
C6 C 0.5451(17) 0.3785(4) 0.6769(2) 0.031(2) Uani 1.000000 G . .
C5 C 0.4302(16) 0.4941(5) 0.6677(2) 0.033(2) Uani 1.000000 G . .
C4 C 0.4975(19) 0.5879(4) 0.7010(2) 0.051(3) Uani 1.000000 G . .
H4 H 0.4190(19) 0.6669(4) 0.6948(2) 0.061(4) Uiso 1.000000 R . .
C3 C 0.680(2) 0.5661(5) 0.7435(2) 0.046(3) Uani 1.000000 G . .
H3 H 0.726(2) 0.6302(5) 0.7663(2) 0.055(4) Uiso 1.000000 R . .
C11 C 0.3244(17) 0.1359(4) 0.5806(2) 0.036(2) Uani 1.000000 D U .
C10 C 0.1455(16) 0.2119(5) 0.55043(19) 0.033(2) Uani 1.000000 G . .
H10 H 0.0470(16) 0.1810(5) 0.52097(19) 0.040(3) Uiso 1.000000 R . .
C9 C 0.1108(15) 0.3332(5) 0.5634(2) 0.043(3) Uani 1.000000 G . .
H9 H -0.0114(15) 0.3851(5) 0.5428(2) 0.052(4) Uiso 1.000000 R . .
C8 C 0.2550(16) 0.3784(4) 0.6065(2) 0.029(2) Uani 1.000000 G . .
C7 C 0.4339(15) 0.3024(5) 0.6366(2) 0.032(2) Uani 1.000000 G . .
C12 C 0.4686(16) 0.1811(5) 0.6237(2) 0.032(2) Uani 1.000000 G . .
H12 H 0.5908(16) 0.1292(5) 0.6443(2) 0.038(3) Uiso 1.000000 R . .
C13 C 0.084(3) 0.5949(10) 0.6026(4) 0.043(3) Uani 1.000000 . . .
H13a H -0.105(3) 0.5641(10) 0.5855(4) 0.052(3) Uiso 1.000000 R . .
H13b H 0.017(3) 0.6515(10) 0.6296(4) 0.052(3) Uiso 1.000000 R . .
C14 C 0.284(4) 0.6626(11) 0.5646(5) 0.060(4) Uani 1.000000 . . .
H14a H 0.386(18) 0.6043(12) 0.542(2) 0.090(6) Uiso 1.000000 GR . .
H14b H 0.153(5) 0.717(6) 0.545(2) 0.090(6) Uiso 1.000000 GR . .
H14c H 0.442(14) 0.710(7) 0.5826(6) 0.090(6) Uiso 1.000000 GR . .
Br1 Br 1.0302(6) 0.4133(2) 0.81212(9) 0.0428(7) Uani 0.626(5) . . 1
O1 O 0.263(4) -0.0338(11) 0.5265(5) 0.058(4) Uani 0.626(5) D U 1
C15 C 0.353(7) 0.0137(15) 0.5651(8) 0.043(4) Uani 0.626(5) D U 1
H15 H 0.456(7) -0.0383(15) 0.5883(8) 0.051(5) Uiso 0.626(5) R . 1
Br1A Br 0.3951(13) -0.0268(3) 0.56363(18) 0.0547(15) Uani 0.374(5) . . 2
O1A O 1.072(7) 0.356(3) 0.8163(12) 0.055(8) Uani 0.374(5) D U 2
C15A C 0.987(11) 0.451(3) 0.7976(14) 0.039(5) Uani 0.374(5) D U 2
H15A H 1.048(11) 0.525(3) 0.8125(14) 0.047(6) Uiso 0.374(5) R . 2


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
N1 C5 1.367(10) . ?
N1 C8 1.375(9) . ?
N1 C13 1.445(13) . ?
C2 C1 1.3900 . ?
C2 C3 1.3900 . ?
C2 Br1 1.915(5) . ?
C2 C15A 1.45(4) . ?
C1 H1 0.9500 . ?
C1 C6 1.3900 . ?
C6 C5 1.3900 . ?
C6 C7 1.436(6) . ?
C5 C4 1.3900 . ?
C4 H4 0.9500 . ?
C4 C3 1.3900 . ?
C3 H3 0.9500 . ?
C11 C10 1.3900 . ?
C11 C12 1.3900 . ?
C11 C15 1.415(15) . ?
C11 Br1A 1.876(5) . ?
C10 H10 0.9500 . ?
C10 C9 1.3900 . ?
C9 H9 0.9500 . ?
C9 C8 1.3900 . ?
C8 C7 1.3900 . ?
C7 C12 1.3900 . ?
C12 H12 0.9500 . ?
C13 H13a 0.9900 . ?
C13 H13b 0.9900 . ?
C13 C14 1.520(16) . ?
C14 H14a 0.9800 . ?
C14 H14b 0.9800 . ?
C14 H14c 0.9800 . ?
O1 C15 1.210(17) . ?
C15 H15 0.9500 . ?
O1A C15A 1.207(19) . ?
C15A H15A 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
C8 N1 C5 106.3(6) . . ?
C13 N1 C5 128.6(9) . . ?
C13 N1 C8 125.1(9) . . ?
C3 C2 C1 120.0 . . ?
Br1 C2 C1 118.1 . . ?
Br1 C2 C3 121.9 . . ?
C15A C2 C1 129.7(14) . . ?
C15A C2 C3 110.2(14) . . ?
C15A C2 Br1 12.6(13) . . ?
H1 C1 C2 120.0(2) . . ?
C6 C1 C2 120.0 . . ?
C6 C1 H1 120.0(2) . . ?
C5 C6 C1 120.0 . . ?
C7 C6 C1 133.2(5) . . ?
C7 C6 C5 106.8(5) . . ?
C6 C5 N1 110.5(5) . . ?
C4 C5 N1 129.5(5) . . ?
C4 C5 C6 120.0 . . ?
H4 C4 C5 120.0(2) . . ?
C3 C4 C5 120.0 . . ?
C3 C4 H4 120.0(2) . . ?
C4 C3 C2 120.0 . . ?
H3 C3 C2 120.0(2) . . ?
H3 C3 C4 120.0(2) . . ?
C12 C11 C10 120.0 . . ?
C15 C11 C10 117.2 . . ?
C15 C11 C12 122.8 . . ?
Br1A C11 C10 122.1(4) . . ?
Br1A C11 C12 117.9(4) . . ?
Br1A C11 C15 5.2(11) . . ?
H10 C10 C11 120.00(18) . . ?
C9 C10 C11 120.0 . . ?
C9 C10 H10 120.00(18) . . ?
H9 C9 C10 120.00(18) . . ?
C8 C9 C10 120.0 . . ?
C8 C9 H9 120.00(18) . . ?
C9 C8 N1 128.5(6) . . ?
C7 C8 N1 111.5(6) . . ?
C7 C8 C9 120.0 . . ?
C8 C7 C6 104.8(4) . . ?
C12 C7 C6 135.2(4) . . ?
C12 C7 C8 120.0 . . ?
C7 C12 C11 120.0 . . ?
H12 C12 C11 120.00(18) . . ?
H12 C12 C7 120.00(18) . . ?
H13a C13 N1 109.3(7) . . ?
H13b C13 N1 109.3(6) . . ?
H13b C13 H13a 108.0 . . ?
C14 C13 N1 111.6(9) . . ?
C14 C13 H13a 109.3(8) . . ?
C14 C13 H13b 109.3(7) . . ?
H14a C14 C13 109.5 . . ?
H14b C14 C13 109.5 . . ?
H14b C14 H14a 109.5 . . ?
H14c C14 C13 109.5 . . ?
H14c C14 H14a 109.5 . . ?
H14c C14 H14b 109.5 . . ?
O1 C15 C11 129.0(18) . . ?
H15 C15 C11 115.5(9) . . ?
H15 C15 O1 115.5(11) . . ?
O1A C15A C2 121(4) . . ?
H15A C15A C2 119.7(13) . . ?
H15A C15A O1A 120(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
N1 C5 C6 C1 -178.0(5) . . . . ?
N1 C5 C6 C7 1.3(8) . . . . ?
N1 C5 C4 C3 177.6(6) . . . . ?
N1 C8 C9 C10 179.6(5) . . . . ?
N1 C8 C7 C6 0.1(8) . . . . ?
N1 C8 C7 C12 -179.7(5) . . . . ?
C2 C1 C6 C5 -0.0(6) . . . . ?
C2 C1 C6 C7 -179.1(4) . . . . ?
C2 C3 C4 C5 0.0(6) . . . . ?
C1 C6 C5 C4 0.0(6) . . . . ?
C1 C6 C7 C8 178.3(6) . . . . ?
C1 C6 C7 C12 -1.9(9) . . . . ?
C6 C5 C4 C3 -0.0(5) . . . . ?
C6 C7 C8 C9 179.8(3) . . . . ?
C6 C7 C12 C11 -179.8(5) . . . . ?
C11 C10 C9 C8 0.0(5) . . . . ?
C11 C12 C7 C8 0.0(5) . . . . ?
C10 C9 C8 C7 -0.0(5) . . . . ?
C9 C8 C7 C12 0.0(6) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_distance_atom_site_label_1
_restr_distance_atom_site_label_2
_restr_distance_site_symmetry_2
_restr_distance_target
_restr_distance_target_weight_param
_restr_distance_diff
C11 C15 1 1.4000 0.0200 -0.0149
C15 O1 1 1.2000 0.0200 -0.0100
C15A O1A 1 1.2000 0.0200 -0.0069

loop_
_restr_U_similar_atom_site_label_1
_restr_U_similar_atom_site_label_2
_restr_U_similar_weight_param
C2 C15A 0.0100
C11 C15 0.0100
O1 C15 0.0200
O1A C15A 0.0200

