# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2022

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

data_2
_database_code_depnum_ccdc_archive 'CCDC 2042977'
loop_
_audit_author_name
_audit_author_address
maoht
;Northeast Normal University
China
;
_audit_update_record             
;
2020-11-07 deposited with the CCDC.	2022-03-20 downloaded from the CCDC.
;
_audit_creation_date             2020-10-19
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2019.05.30 svn.r3610 for OlexSys, GUI svn.r5794)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H14 Br N O2 S'
_chemical_formula_sum            'C19 H14 Br N O2 S'
_chemical_formula_weight         400.28
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.126(2)
_cell_length_b                   8.146(2)
_cell_length_c                   13.660(4)
_cell_angle_alpha                95.851(15)
_cell_angle_beta                 97.291(16)
_cell_angle_gamma                112.652(14)
_cell_volume                     816.4(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4527
_cell_measurement_temperature    172.99
_cell_measurement_theta_max      25.127
_cell_measurement_theta_min      1.628
_shelx_estimated_absorpt_T_max   0.452
_shelx_estimated_absorpt_T_min   0.397
_exptl_absorpt_coefficient_mu    4.720
_exptl_absorpt_correction_T_max  0.389
_exptl_absorpt_correction_T_min  0.37
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_av_unetI/netI     0.0767
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6428
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        64.152
_diffrn_reflns_theta_max         64.152
_diffrn_reflns_theta_min         3.307
_diffrn_ambient_temperature      172.99
_diffrn_detector                 'charge-coupled device (CCD) area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker APEX II'
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Quazar'
_diffrn_measurement_method       '0.5° ω and 0.5° φ scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_detector       'Bruker APEX II'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2269
_reflns_number_total             2650
_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       'SAINT+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_collection       'APEX3 Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2015b)'
_computing_structure_solution    'XT (Sheldrick, 2015a)'
_refine_diff_density_max         1.086
_refine_diff_density_min         -0.733
_refine_diff_density_rms         0.148
_refine_ls_extinction_coef       0.015(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         2650
_refine_ls_number_restraints     57
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0804
_refine_ls_restrained_S_all      1.029
_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)+(0.2500P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2703
_refine_ls_wR_factor_ref         0.2865
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C26) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Rigid body (RIGU) restrains
 C20, C24, Br2, C21, C25, C22, C26, C23
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Fixed Sof: Br1(0.8) C9(0.8) C11(0.8) C14(0.8) C16(0.8) H16(0.8) C17(0.8)
 H17(0.8) C18(0.8) H18(0.8) C19(0.8) H19A(0.8) H19B(0.8) H19C(0.8) C20(0.2)
 C21(0.2) H21(0.2) C22(0.2) C23(0.2) C24(0.2) H24(0.2) C25(0.2) H25(0.2)
 Br2(0.2) C26(0.2) H26A(0.2) H26B(0.2) H26C(0.2)
5.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C12(H12), C13(H13), C15(H15),
 C16(H16), C17(H17), C18(H18), C21(H21), C24(H24), C25(H25)
5.b Fitted hexagon refined as free rotating group:
 C20(C21,C22,C23,C24,C25)
5.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.08030(11) 0.85634(11) 0.62999(5) 0.0479(5) Uani 0.8 1 d . . P A 1
S1 S 0.15950(17) 0.37176(19) 0.11636(12) 0.0381(6) Uani 1 1 d . . . . .
O1 O 0.0383(5) 0.2743(6) 0.0244(4) 0.0523(13) Uani 1 1 d . . . . .
O2 O 0.0872(6) 0.4475(6) 0.1918(4) 0.0518(13) Uani 1 1 d . . . . .
N1 N 0.5284(6) 0.5078(6) 0.2425(4) 0.0323(11) Uani 1 1 d . . . . .
C1 C 0.5098(7) 0.6081(7) 0.1673(4) 0.0290(12) Uani 1 1 d . . . . .
C2 C 0.4281(7) 0.3237(8) 0.2326(4) 0.0335(13) Uani 1 1 d . . . . .
C3 C 0.2601(7) 0.2394(8) 0.1691(5) 0.0353(13) Uani 1 1 d . . . . .
C4 C 0.3514(7) 0.5462(7) 0.0953(4) 0.0336(13) Uani 1 1 d . . . . .
C5 C 0.1680(8) 0.0508(8) 0.1502(5) 0.0411(15) Uani 1 1 d . . . . .
H5 H 0.055751 -0.004166 0.104837 0.049 Uiso 1 1 calc R U . . .
C6 C 0.6482(7) 0.7656(8) 0.1563(4) 0.0334(13) Uani 1 1 d . . . . .
H6 H 0.755668 0.816326 0.205596 0.040 Uiso 1 1 calc R U . . .
C7 C 0.3387(8) 0.6321(8) 0.0119(4) 0.0360(13) Uani 1 1 d . . . . .
H7 H 0.231527 0.584106 -0.037540 0.043 Uiso 1 1 calc R U . . .
C8 C 0.6342(8) 0.8526(8) 0.0744(5) 0.0410(15) Uani 1 1 d . . . . .
H8 H 0.732087 0.960295 0.068457 0.049 Uiso 1 1 calc R U . . .
C9 C 0.6627(11) 0.5939(13) 0.3339(7) 0.035(2) Uani 0.8 1 d . . P A 1
C10 C 0.4802(8) 0.7835(9) 0.0028(5) 0.0411(14) Uani 1 1 d . . . . .
H10 H 0.472605 0.841793 -0.053355 0.049 Uiso 1 1 calc R U . . .
C11 C 0.9721(10) 0.6910(10) 0.4235(6) 0.0279(16) Uani 0.8 1 d . . P A 1
C12 C 0.4946(8) 0.2138(8) 0.2818(5) 0.0395(14) Uani 1 1 d . . . . .
H12 H 0.605977 0.268622 0.327920 0.047 Uiso 1 1 calc R U . . .
C13 C 0.2402(9) -0.0554(8) 0.1974(5) 0.0447(16) Uani 1 1 d . . . . .
H13 H 0.179476 -0.183132 0.183793 0.054 Uiso 1 1 calc R U . . .
C14 C 0.9161(11) 0.7514(12) 0.5063(6) 0.0342(18) Uani 0.8 1 d . . P A 1
C15 C 0.4050(9) 0.0290(9) 0.2659(5) 0.0472(17) Uani 1 1 d . . . . .
H15 H 0.454076 -0.041388 0.301045 0.057 Uiso 1 1 calc R U . . .
C16 C 0.8423(10) 0.6101(10) 0.3379(6) 0.0311(16) Uani 0.8 1 d . . P A 1
H16 H 0.875140 0.564262 0.280186 0.037 Uiso 0.8 1 calc R U P A 1
C17 C 0.6135(10) 0.6581(12) 0.4155(6) 0.0398(19) Uani 0.8 1 d . . P A 1
H17 H 0.492239 0.647248 0.412809 0.048 Uiso 0.8 1 calc R U P A 1
C18 C 0.7395(10) 0.7398(11) 0.5032(6) 0.0408(18) Uani 0.8 1 d . . P A 1
H18 H 0.706051 0.787151 0.560223 0.049 Uiso 0.8 1 calc R U P A 1
C19 C 1.1651(10) 0.7058(11) 0.4276(7) 0.0427(18) Uani 0.8 1 d . . P A 1
H19A H 1.248402 0.833199 0.437354 0.064 Uiso 0.8 1 calc R U P A 1
H19B H 1.174317 0.643179 0.364684 0.064 Uiso 0.8 1 calc R U P A 1
H19C H 1.197209 0.650588 0.483359 0.064 Uiso 0.8 1 calc R U P A 1
C20 C 0.689(2) 0.585(4) 0.3143(16) 0.029(7) Uani 0.2 1 d G . P A 2
C21 C 0.697(3) 0.665(3) 0.4108(17) 0.030(5) Uani 0.2 1 d G . P A 2
H21 H 0.591053 0.671621 0.430259 0.036 Uiso 0.2 1 calc R U P A 2
C22 C 0.859(4) 0.734(3) 0.4787(14) 0.036(6) Uani 0.2 1 d G . P A 2
C23 C 1.014(3) 0.723(4) 0.4502(16) 0.066(15) Uani 0.2 1 d G . P A 2
C24 C 1.005(2) 0.644(3) 0.3537(16) 0.034(5) Uani 0.2 1 d G . P A 2
H24 H 1.110966 0.636804 0.334261 0.041 Uiso 0.2 1 calc R U P A 2
C25 C 0.843(2) 0.575(3) 0.2858(13) 0.031(5) Uani 0.2 1 d G . P A 2
H25 H 0.837416 0.520338 0.219839 0.037 Uiso 0.2 1 calc R U P A 2
Br2 Br 1.2451(7) 0.8299(7) 0.5301(4) 0.0755(14) Uani 0.2 1 d . . P A 2
C26 C 0.896(5) 0.825(5) 0.585(3) 0.053(6) Uani 0.2 1 d . U P A 2
H26A H 0.792003 0.851274 0.597914 0.079 Uiso 0.2 1 calc R U P A 2
H26B H 1.004575 0.937481 0.595699 0.079 Uiso 0.2 1 calc R U P A 2
H26C H 0.914656 0.745239 0.630007 0.079 Uiso 0.2 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
Br1 C14 1.903(9) . ?
S1 O1 1.435(5) . ?
S1 O2 1.447(4) . ?
S1 C3 1.742(6) . ?
S1 C4 1.739(6) . ?
N1 C1 1.404(7) . ?
N1 C2 1.386(8) . ?
N1 C9 1.459(10) . ?
N1 C20 1.404(16) . ?
C1 C4 1.399(8) . ?
C1 C6 1.380(8) . ?
C2 C3 1.395(8) . ?
C2 C12 1.396(9) . ?
C3 C5 1.404(8) . ?
C4 C7 1.409(9) . ?
C5 H5 0.9500 . ?
C5 C13 1.384(10) . ?
C6 H6 0.9500 . ?
C6 C8 1.400(9) . ?
C7 H7 0.9500 . ?
C7 C10 1.355(9) . ?
C8 H8 0.9500 . ?
C8 C10 1.369(9) . ?
C9 C16 1.407(10) . ?
C9 C17 1.354(13) . ?
C10 H10 0.9500 . ?
C11 C14 1.384(11) . ?
C11 C16 1.382(12) . ?
C11 C19 1.520(10) . ?
C12 H12 0.9500 . ?
C12 C15 1.375(9) . ?
C13 H13 0.9500 . ?
C13 C15 1.409(10) . ?
C14 C18 1.397(11) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C17 C18 1.388(12) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.3900 . ?
C20 C25 1.3900 . ?
C21 H21 0.9500 . ?
C21 C22 1.3900 . ?
C22 C23 1.3900 . ?
C22 C26 1.50(4) . ?
C23 C24 1.3900 . ?
C23 Br2 1.874(16) . ?
C24 H24 0.9500 . ?
C24 C25 1.3900 . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 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
O1 S1 O2 117.4(3) . . ?
O1 S1 C3 110.4(3) . . ?
O1 S1 C4 111.5(3) . . ?
O2 S1 C3 109.2(3) . . ?
O2 S1 C4 107.2(3) . . ?
C4 S1 C3 99.8(3) . . ?
C1 N1 C9 120.5(6) . . ?
C2 N1 C1 122.6(5) . . ?
C2 N1 C9 116.8(6) . . ?
C2 N1 C20 117.7(13) . . ?
C20 N1 C1 116.8(12) . . ?
C4 C1 N1 121.0(5) . . ?
C6 C1 N1 122.6(5) . . ?
C6 C1 C4 116.3(5) . . ?
N1 C2 C3 121.1(5) . . ?
N1 C2 C12 121.6(5) . . ?
C3 C2 C12 117.2(5) . . ?
C2 C3 S1 119.1(4) . . ?
C2 C3 C5 121.1(6) . . ?
C5 C3 S1 119.7(5) . . ?
C1 C4 S1 118.4(5) . . ?
C1 C4 C7 121.8(5) . . ?
C7 C4 S1 119.5(4) . . ?
C3 C5 H5 119.8 . . ?
C13 C5 C3 120.3(6) . . ?
C13 C5 H5 119.8 . . ?
C1 C6 H6 119.2 . . ?
C1 C6 C8 121.6(5) . . ?
C8 C6 H6 119.2 . . ?
C4 C7 H7 120.2 . . ?
C10 C7 C4 119.6(5) . . ?
C10 C7 H7 120.2 . . ?
C6 C8 H8 119.8 . . ?
C10 C8 C6 120.4(6) . . ?
C10 C8 H8 119.8 . . ?
C16 C9 N1 120.6(8) . . ?
C17 C9 N1 119.5(7) . . ?
C17 C9 C16 119.9(8) . . ?
C7 C10 C8 120.1(6) . . ?
C7 C10 H10 120.0 . . ?
C8 C10 H10 120.0 . . ?
C14 C11 C19 121.7(8) . . ?
C16 C11 C14 116.8(7) . . ?
C16 C11 C19 121.4(7) . . ?
C2 C12 H12 118.8 . . ?
C15 C12 C2 122.5(6) . . ?
C15 C12 H12 118.8 . . ?
C5 C13 H13 120.5 . . ?
C5 C13 C15 118.9(6) . . ?
C15 C13 H13 120.5 . . ?
C11 C14 Br1 120.7(6) . . ?
C11 C14 C18 122.2(8) . . ?
C18 C14 Br1 117.1(6) . . ?
C12 C15 C13 119.8(7) . . ?
C12 C15 H15 120.1 . . ?
C13 C15 H15 120.1 . . ?
C9 C16 H16 119.1 . . ?
C11 C16 C9 121.7(7) . . ?
C11 C16 H16 119.1 . . ?
C9 C17 H17 119.9 . . ?
C9 C17 C18 120.2(7) . . ?
C18 C17 H17 119.9 . . ?
C14 C18 H18 120.5 . . ?
C17 C18 C14 119.0(7) . . ?
C17 C18 H18 120.5 . . ?
C11 C19 H19A 109.5 . . ?
C11 C19 H19B 109.5 . . ?
C11 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 N1 123.2(14) . . ?
C21 C20 C25 120.0 . . ?
C25 C20 N1 116.7(14) . . ?
C20 C21 H21 120.0 . . ?
C20 C21 C22 120.0 . . ?
C22 C21 H21 120.0 . . ?
C21 C22 C23 120.0 . . ?
C21 C22 C26 128(2) . . ?
C23 C22 C26 112(2) . . ?
C22 C23 Br2 124.3(14) . . ?
C24 C23 C22 120.0 . . ?
C24 C23 Br2 115.4(14) . . ?
C23 C24 H24 120.0 . . ?
C23 C24 C25 120.0 . . ?
C25 C24 H24 120.0 . . ?
C20 C25 H25 120.0 . . ?
C24 C25 C20 120.0 . . ?
C24 C25 H25 120.0 . . ?
C22 C26 H26A 109.5 . . ?
C22 C26 H26B 109.5 . . ?
C22 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

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
Br1 C14 C18 C17 -177.6(7) . . . . ?
S1 C3 C5 C13 -175.2(5) . . . . ?
S1 C4 C7 C10 170.8(4) . . . . ?
O1 S1 C3 C2 154.4(5) . . . . ?
O1 S1 C3 C5 -28.0(5) . . . . ?
O1 S1 C4 C1 -155.7(4) . . . . ?
O1 S1 C4 C7 30.4(5) . . . . ?
O2 S1 C3 C2 -75.1(5) . . . . ?
O2 S1 C3 C5 102.4(5) . . . . ?
O2 S1 C4 C1 74.6(5) . . . . ?
O2 S1 C4 C7 -99.3(5) . . . . ?
N1 C1 C4 S1 14.6(6) . . . . ?
N1 C1 C4 C7 -171.6(5) . . . . ?
N1 C1 C6 C8 172.7(5) . . . . ?
N1 C2 C3 S1 -9.8(7) . . . . ?
N1 C2 C3 C5 172.6(5) . . . . ?
N1 C2 C12 C15 -173.9(5) . . . . ?
N1 C9 C16 C11 -180.0(8) . . . . ?
N1 C9 C17 C18 179.8(8) . . . . ?
N1 C20 C21 C22 178(3) . . . . ?
N1 C20 C25 C24 -178(2) . . . . ?
C1 N1 C2 C3 -25.2(8) . . . . ?
C1 N1 C2 C12 151.7(5) . . . . ?
C1 N1 C9 C16 -86.4(9) . . . . ?
C1 N1 C9 C17 93.8(10) . . . . ?
C1 N1 C20 C21 103.6(17) . . . . ?
C1 N1 C20 C25 -78.2(15) . . . . ?
C1 C4 C7 C10 -2.9(8) . . . . ?
C1 C6 C8 C10 0.6(8) . . . . ?
C2 N1 C1 C4 22.6(7) . . . . ?
C2 N1 C1 C6 -153.5(5) . . . . ?
C2 N1 C9 C16 90.8(9) . . . . ?
C2 N1 C9 C17 -89.0(9) . . . . ?
C2 N1 C20 C21 -95.0(18) . . . . ?
C2 N1 C20 C25 83.3(14) . . . . ?
C2 C3 C5 C13 2.3(9) . . . . ?
C2 C12 C15 C13 0.4(9) . . . . ?
C3 S1 C4 C1 -39.1(4) . . . . ?
C3 S1 C4 C7 147.0(4) . . . . ?
C3 C2 C12 C15 3.1(9) . . . . ?
C3 C5 C13 C15 1.3(9) . . . . ?
C4 S1 C3 C2 37.0(5) . . . . ?
C4 S1 C3 C5 -145.5(5) . . . . ?
C4 C1 C6 C8 -3.5(7) . . . . ?
C4 C7 C10 C8 -0.2(8) . . . . ?
C5 C13 C15 C12 -2.6(9) . . . . ?
C6 C1 C4 S1 -169.1(4) . . . . ?
C6 C1 C4 C7 4.7(7) . . . . ?
C6 C8 C10 C7 1.4(9) . . . . ?
C9 N1 C1 C4 -160.3(6) . . . . ?
C9 N1 C1 C6 23.6(8) . . . . ?
C9 N1 C2 C3 157.6(6) . . . . ?
C9 N1 C2 C12 -25.5(8) . . . . ?
C9 C17 C18 C14 -1.2(13) . . . . ?
C11 C14 C18 C17 2.8(13) . . . . ?
C12 C2 C3 S1 173.2(4) . . . . ?
C12 C2 C3 C5 -4.4(8) . . . . ?
C14 C11 C16 C9 1.6(11) . . . . ?
C16 C9 C17 C18 0.0(13) . . . . ?
C16 C11 C14 Br1 177.5(6) . . . . ?
C16 C11 C14 C18 -3.0(12) . . . . ?
C17 C9 C16 C11 -0.2(13) . . . . ?
C19 C11 C14 Br1 -0.1(11) . . . . ?
C19 C11 C14 C18 179.5(8) . . . . ?
C19 C11 C16 C9 179.2(7) . . . . ?
C20 N1 C1 C4 -177.0(11) . . . . ?
C20 N1 C1 C6 7.0(12) . . . . ?
C20 N1 C2 C3 174.5(11) . . . . ?
C20 N1 C2 C12 -8.6(12) . . . . ?
C20 C21 C22 C23 0.0 . . . . ?
C20 C21 C22 C26 180(3) . . . . ?
C21 C20 C25 C24 0.0 . . . . ?
C21 C22 C23 C24 0.0 . . . . ?
C21 C22 C23 Br2 174(2) . . . . ?
C22 C23 C24 C25 0.0 . . . . ?
C23 C24 C25 C20 0.0 . . . . ?
C25 C20 C21 C22 0.0 . . . . ?
Br2 C23 C24 C25 -175(2) . . . . ?
C26 C22 C23 C24 -180(2) . . . . ?
C26 C22 C23 Br2 -5.6(19) . . . . ?

_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_1
_database_code_depnum_ccdc_archive 'CCDC 2042978'
loop_
_audit_author_name
_audit_author_address
maoht
;Northeast Normal University
China
;
_audit_update_record             
;
2020-11-07 deposited with the CCDC.	2022-03-20 downloaded from the CCDC.
;
_audit_creation_date             2020-10-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H16 Br N O2 S'
_chemical_formula_sum            'C20 H16 Br N O2 S'
_chemical_formula_weight         414.31
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.2210(16)
_cell_length_b                   8.4240(17)
_cell_length_c                   14.349(3)
_cell_angle_alpha                94.358(15)
_cell_angle_beta                 98.812(13)
_cell_angle_gamma                114.597(13)
_cell_volume                     882.0(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4368
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.127
_cell_measurement_theta_min      1.628
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.390
_exptl_absorpt_correction_T_max  0.87
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0939
_diffrn_reflns_av_unetI/netI     0.0770
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11607
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        62.834
_diffrn_reflns_theta_max         62.834
_diffrn_reflns_theta_min         3.155
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'charge-coupled device (CCD) area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker APEX II'
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Quazar'
_diffrn_measurement_method       '0.5° ω and 0.5° φ scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_detector       'Bruker APEX II'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1953
_reflns_number_total             2820
_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       'SAINT+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_collection       'APEX3 Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2015b)'
_computing_structure_solution    'XT (Sheldrick, 2015a)'
_refine_diff_density_max         0.912
_refine_diff_density_min         -0.803
_refine_diff_density_rms         0.170
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2820
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1142
_refine_ls_R_factor_gt           0.0809
_refine_ls_restrained_S_all      1.039
_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)+(0.1752P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2200
_refine_ls_wR_factor_ref         0.2506
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C10(H10), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.11861(13) 0.84047(12) 0.59393(6) 0.0701(5) Uani 1 1 d . . . . .
S1 S 0.1671(2) 0.3625(2) 0.11390(14) 0.0437(5) Uani 1 1 d . . . . .
O1 O 0.1025(7) 0.4264(7) 0.1893(5) 0.0661(17) Uani 1 1 d . . . . .
O2 O 0.0376(7) 0.2713(8) 0.0276(4) 0.0673(16) Uani 1 1 d . . . . .
N1 N 0.5479(7) 0.4997(7) 0.2274(4) 0.0372(13) Uani 1 1 d . . . . .
C1 C 0.4436(8) 0.3167(8) 0.2156(4) 0.0318(14) Uani 1 1 d . . . . .
C2 C 0.9950(9) 0.6749(9) 0.3993(5) 0.0400(16) Uani 1 1 d . . . . .
C3 C 0.8641(9) 0.6002(9) 0.3155(5) 0.0390(16) Uani 1 1 d . . . . .
H3 H 0.894856 0.560530 0.261606 0.047 Uiso 1 1 calc R . . . .
C4 C 0.5219(8) 0.6018(9) 0.1587(5) 0.0365(15) Uani 1 1 d . . . . .
C5 C 0.6902(8) 0.5841(8) 0.3111(5) 0.0342(15) Uani 1 1 d . . . . .
C6 C 0.6452(9) 0.6459(9) 0.3913(5) 0.0413(17) Uani 1 1 d . . . . .
H6 H 0.526740 0.634428 0.387453 0.050 Uiso 1 1 calc R . . . .
C7 C 0.9449(9) 0.7357(9) 0.4769(5) 0.0405(16) Uani 1 1 d . . . . .
C8 C 0.7685(10) 0.7229(9) 0.4760(5) 0.0418(17) Uani 1 1 d . . . . .
C9 C 0.3562(8) 0.5409(9) 0.0935(5) 0.0368(15) Uani 1 1 d . . . . .
C10 C 0.5137(9) 0.2086(9) 0.2571(5) 0.0413(16) Uani 1 1 d . . . . .
H10 H 0.629081 0.260027 0.296577 0.050 Uiso 1 1 calc R . . . .
C11 C 0.2698(8) 0.2316(9) 0.1594(4) 0.0342(15) Uani 1 1 d . . . . .
C12 C 0.3351(10) 0.6290(10) 0.0170(5) 0.0468(18) Uani 1 1 d . . . . .
H12 H 0.226170 0.583019 -0.028040 0.056 Uiso 1 1 calc R . . . .
C13 C 0.6601(9) 0.7608(9) 0.1502(5) 0.0454(18) Uani 1 1 d . . . . .
H13 H 0.770134 0.807923 0.194367 0.054 Uiso 1 1 calc R . . . .
C14 C 0.2464(10) -0.0542(10) 0.1806(5) 0.0491(19) Uani 1 1 d . . . . .
H14 H 0.183484 -0.176778 0.167354 0.059 Uiso 1 1 calc R . . . .
C15 C 0.4769(11) 0.7836(11) 0.0096(5) 0.0497(19) Uani 1 1 d . . . . .
H15 H 0.465384 0.843483 -0.041012 0.060 Uiso 1 1 calc R . . . .
C16 C 0.1728(9) 0.0499(10) 0.1404(5) 0.0451(18) Uani 1 1 d . . . . .
H16 H 0.057765 -0.001684 0.100510 0.054 Uiso 1 1 calc R . . . .
C17 C 0.4165(11) 0.0267(10) 0.2412(5) 0.0509(19) Uani 1 1 d . . . . .
H17 H 0.465621 -0.041976 0.271466 0.061 Uiso 1 1 calc R . . . .
C18 C 0.6362(10) 0.8506(10) 0.0765(6) 0.0498(19) Uani 1 1 d . . . . .
H18 H 0.730158 0.958569 0.072397 0.060 Uiso 1 1 calc R . . . .
C19 C 1.1821(10) 0.6838(12) 0.4019(7) 0.063(2) Uani 1 1 d . . . . .
H19A H 1.205801 0.615830 0.448328 0.095 Uiso 1 1 calc GR . . . .
H19B H 1.271909 0.804629 0.418811 0.095 Uiso 1 1 calc GR . . . .
H19C H 1.188122 0.636769 0.340102 0.095 Uiso 1 1 calc GR . . . .
C20 C 0.7156(13) 0.7881(12) 0.5617(6) 0.067(2) Uani 1 1 d . . . . .
H20A H 0.786163 0.913726 0.578441 0.101 Uiso 1 1 calc GR . . . .
H20B H 0.738991 0.731545 0.614375 0.101 Uiso 1 1 calc GR . . . .
H20C H 0.588022 0.760655 0.546967 0.101 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C7 1.905(7) . ?
S1 O1 1.438(5) . ?
S1 O2 1.424(6) . ?
S1 C9 1.738(7) . ?
S1 C11 1.752(7) . ?
N1 C1 1.398(8) . ?
N1 C4 1.406(8) . ?
N1 C5 1.436(8) . ?
C1 C10 1.389(10) . ?
C1 C11 1.383(9) . ?
C2 C3 1.388(10) . ?
C2 C7 1.378(10) . ?
C2 C19 1.503(9) . ?
C3 C5 1.370(9) . ?
C4 C9 1.396(9) . ?
C4 C13 1.378(9) . ?
C5 C6 1.390(10) . ?
C6 C8 1.371(10) . ?
C7 C8 1.407(10) . ?
C8 C20 1.504(10) . ?
C9 C12 1.400(10) . ?
C10 C17 1.383(10) . ?
C11 C16 1.381(10) . ?
C12 C15 1.364(11) . ?
C13 C18 1.382(10) . ?
C14 C16 1.371(11) . ?
C14 C17 1.386(11) . ?
C15 C18 1.369(11) . ?

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
O1 S1 C9 107.3(3) . . ?
O1 S1 C11 108.3(3) . . ?
O2 S1 O1 117.0(4) . . ?
O2 S1 C9 111.7(4) . . ?
O2 S1 C11 110.6(3) . . ?
C9 S1 C11 100.7(3) . . ?
C1 N1 C4 122.1(5) . . ?
C1 N1 C5 118.6(5) . . ?
C4 N1 C5 119.3(5) . . ?
C10 C1 N1 121.2(6) . . ?
C11 C1 N1 122.8(6) . . ?
C11 C1 C10 116.0(6) . . ?
C3 C2 C19 119.0(7) . . ?
C7 C2 C3 117.7(6) . . ?
C7 C2 C19 123.3(7) . . ?
C5 C3 C2 120.9(6) . . ?
C9 C4 N1 120.7(6) . . ?
C13 C4 N1 121.7(6) . . ?
C13 C4 C9 117.6(6) . . ?
C3 C5 N1 122.8(6) . . ?
C3 C5 C6 119.5(6) . . ?
C6 C5 N1 117.7(6) . . ?
C8 C6 C5 122.6(6) . . ?
C2 C7 Br1 119.7(5) . . ?
C2 C7 C8 123.7(6) . . ?
C8 C7 Br1 116.6(5) . . ?
C6 C8 C7 115.7(6) . . ?
C6 C8 C20 121.4(7) . . ?
C7 C8 C20 123.0(7) . . ?
C4 C9 S1 118.9(5) . . ?
C4 C9 C12 121.6(6) . . ?
C12 C9 S1 119.3(5) . . ?
C17 C10 C1 121.8(6) . . ?
C1 C11 S1 117.8(5) . . ?
C16 C11 S1 119.1(5) . . ?
C16 C11 C1 123.1(6) . . ?
C15 C12 C9 118.9(7) . . ?
C4 C13 C18 120.5(7) . . ?
C16 C14 C17 118.7(7) . . ?
C12 C15 C18 120.1(7) . . ?
C14 C16 C11 119.8(6) . . ?
C10 C17 C14 120.5(7) . . ?
C15 C18 C13 121.2(7) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_maoht201101_0m
_database_code_depnum_ccdc_archive 'CCDC 2042979'
loop_
_audit_author_name
_audit_author_address
maoht
;Northeast Normal University
China
;
_audit_update_record             
;
2020-11-07 deposited with the CCDC.	2022-03-20 downloaded from the CCDC.
;
_audit_creation_date             2020-11-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H20 Br N O2 S'
_chemical_formula_sum            'C22 H20 Br N O2 S'
_chemical_formula_weight         442.36
_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'
N N 0.0061 0.0033 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3574(8)
_cell_length_b                   9.3223(11)
_cell_length_c                   14.2727(16)
_cell_angle_alpha                73.231(7)
_cell_angle_beta                 83.188(6)
_cell_angle_gamma                64.864(5)
_cell_volume                     963.87(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7398
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.127
_cell_measurement_theta_min      1.628
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.258
_exptl_absorpt_correction_T_max  0.87
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0747
_diffrn_reflns_av_unetI/netI     0.0503
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17911
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.048
_diffrn_reflns_theta_max         25.048
_diffrn_reflns_theta_min         2.551
_diffrn_ambient_temperature      298.62
_diffrn_detector                 'charge-coupled device (CCD) area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker APEX II'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Quazar'
_diffrn_measurement_method       '0.5° ω and 0.5° φ scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_detector       'Bruker APEX II'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2691
_reflns_number_total             3401
_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       'SAINT+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_collection       'APEX3 Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2015b)'
_computing_structure_solution    'XT (Sheldrick, 2015a)'
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.789
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3401
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0446
_refine_ls_restrained_S_all      1.074
_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)+(0.0402P)²+1.2845P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.1090
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C14(H14), C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C18(H18A,H18B,
 H18C)
;
_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 0.79945(6) -0.14638(5) 0.60625(3) 0.04516(17) Uani 1 1 d . . . . .
S1 S 0.34768(14) 0.76882(13) 0.12075(8) 0.0456(3) Uani 1 1 d . . . . .
O1 O 0.2310(4) 0.8160(4) 0.1997(3) 0.0648(10) Uani 1 1 d . . . . .
O2 O 0.3174(5) 0.8877(4) 0.0276(3) 0.0740(11) Uani 1 1 d . . . . .
N1 N 0.5586(4) 0.4324(3) 0.2464(2) 0.0260(6) Uani 1 1 d . . . . .
C1 C 0.6176(5) 0.2923(4) 0.3311(2) 0.0253(8) Uani 1 1 d . . . . .
C2 C 0.7249(4) 0.0347(4) 0.4924(3) 0.0271(8) Uani 1 1 d . . . . .
C3 C 0.6383(5) 0.5434(4) 0.2263(3) 0.0278(8) Uani 1 1 d . . . . .
C4 C 0.5780(5) 0.1760(4) 0.5013(2) 0.0263(8) Uani 1 1 d . . . . .
C5 C 0.7636(4) 0.1500(4) 0.3234(2) 0.0257(7) Uani 1 1 d . . . . .
C6 C 0.8195(5) 0.0155(4) 0.4060(3) 0.0286(8) Uani 1 1 d . . . . .
C7 C 0.4402(4) 0.4407(5) 0.1805(2) 0.0293(8) Uani 1 1 d . . . . .
C8 C 0.3473(5) 0.5879(5) 0.1107(3) 0.0368(9) Uani 1 1 d . . . . .
C9 C 0.5222(4) 0.3083(4) 0.4182(2) 0.0249(7) Uani 1 1 d . . . . .
C10 C 0.3596(5) 0.4643(5) 0.4196(3) 0.0368(9) Uani 1 1 d . . . . .
H10A H 0.350964 0.545992 0.359043 0.055 Uiso 1 1 calc GR . . . .
H10B H 0.368598 0.504086 0.472921 0.055 Uiso 1 1 calc GR . . . .
H10C H 0.256241 0.441605 0.427902 0.055 Uiso 1 1 calc GR . . . .
C11 C 0.8000(5) 0.5004(5) 0.2686(3) 0.0378(9) Uani 1 1 d . . . . .
H11 H 0.850412 0.400831 0.315664 0.045 Uiso 1 1 calc R . . . .
C12 C 0.5630(5) 0.6989(4) 0.1601(3) 0.0344(9) Uani 1 1 d . . . . .
C13 C 0.9745(5) -0.1427(5) 0.4013(3) 0.0412(10) Uani 1 1 d . . . . .
H13A H 1.053959 -0.177016 0.454630 0.062 Uiso 1 1 calc GR . . . .
H13B H 1.035238 -0.125874 0.340421 0.062 Uiso 1 1 calc GR . . . .
H13C H 0.933065 -0.226029 0.405825 0.062 Uiso 1 1 calc GR . . . .
C14 C 0.6519(6) 0.8018(5) 0.1329(3) 0.0483(11) Uani 1 1 d . . . . .
H14 H 0.600761 0.903524 0.087766 0.058 Uiso 1 1 calc R . . . .
C15 C 0.4824(6) 0.1854(5) 0.5973(3) 0.0425(10) Uani 1 1 d . . . . .
H15A H 0.436286 0.102802 0.616832 0.064 Uiso 1 1 calc GR . . . .
H15B H 0.386976 0.292011 0.589886 0.064 Uiso 1 1 calc GR . . . .
H15C H 0.563207 0.167240 0.646386 0.064 Uiso 1 1 calc GR . . . .
C16 C 0.4144(5) 0.3024(5) 0.1809(3) 0.0399(10) Uani 1 1 d . . . . .
H16 H 0.469010 0.204427 0.228474 0.048 Uiso 1 1 calc R . . . .
C17 C 0.2430(6) 0.5922(7) 0.0392(3) 0.0539(13) Uani 1 1 d . . . . .
H17 H 0.185532 0.689719 -0.008123 0.065 Uiso 1 1 calc R . . . .
C18 C 0.8579(5) 0.1416(5) 0.2271(3) 0.0386(9) Uani 1 1 d . . . . .
H18A H 0.829043 0.074324 0.198250 0.058 Uiso 1 1 calc GR . . . .
H18B H 0.983168 0.094833 0.237766 0.058 Uiso 1 1 calc GR . . . .
H18C H 0.821455 0.250287 0.183892 0.058 Uiso 1 1 calc GR . . . .
C19 C 0.8134(7) 0.7539(6) 0.1721(4) 0.0526(12) Uani 1 1 d . . . . .
H19 H 0.874566 0.820802 0.152807 0.063 Uiso 1 1 calc R . . . .
C20 C 0.8855(6) 0.6030(6) 0.2417(4) 0.0500(11) Uani 1 1 d . . . . .
H20 H 0.993755 0.571446 0.270367 0.060 Uiso 1 1 calc R . . . .
C21 C 0.3077(6) 0.3101(7) 0.1108(4) 0.0552(13) Uani 1 1 d . . . . .
H21 H 0.291210 0.216947 0.112038 0.066 Uiso 1 1 calc R . . . .
C22 C 0.2257(6) 0.4533(8) 0.0391(3) 0.0599(14) Uani 1 1 d . . . . .
H22 H 0.158749 0.455106 -0.009253 0.072 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C2 1.908(3) . ?
S1 O1 1.440(3) . ?
S1 O2 1.432(3) . ?
S1 C8 1.734(5) . ?
S1 C12 1.735(4) . ?
N1 C1 1.447(4) . ?
N1 C3 1.403(5) . ?
N1 C7 1.407(4) . ?
C1 C5 1.392(5) . ?
C1 C9 1.405(5) . ?
C2 C4 1.394(5) . ?
C2 C6 1.397(5) . ?
C3 C11 1.394(5) . ?
C3 C12 1.402(5) . ?
C4 C9 1.394(5) . ?
C4 C15 1.509(5) . ?
C5 C6 1.400(5) . ?
C5 C18 1.506(5) . ?
C6 C13 1.507(5) . ?
C7 C8 1.403(5) . ?
C7 C16 1.394(6) . ?
C8 C17 1.401(6) . ?
C9 C10 1.514(5) . ?
C11 C20 1.370(6) . ?
C12 C14 1.394(6) . ?
C14 C19 1.363(7) . ?
C16 C21 1.385(6) . ?
C17 C22 1.364(7) . ?
C19 C20 1.394(6) . ?
C21 C22 1.378(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
O1 S1 C8 107.5(2) . . ?
O1 S1 C12 107.9(2) . . ?
O2 S1 O1 117.7(2) . . ?
O2 S1 C8 111.0(2) . . ?
O2 S1 C12 110.7(2) . . ?
C8 S1 C12 100.59(18) . . ?
C3 N1 C1 118.7(3) . . ?
C3 N1 C7 122.2(3) . . ?
C7 N1 C1 118.6(3) . . ?
C5 C1 N1 119.6(3) . . ?
C5 C1 C9 123.1(3) . . ?
C9 C1 N1 117.3(3) . . ?
C4 C2 Br1 117.4(3) . . ?
C4 C2 C6 124.7(3) . . ?
C6 C2 Br1 117.8(3) . . ?
C11 C3 N1 121.0(3) . . ?
C11 C3 C12 117.4(4) . . ?
C12 C3 N1 121.6(3) . . ?
C2 C4 C9 117.7(3) . . ?
C2 C4 C15 121.2(3) . . ?
C9 C4 C15 121.1(3) . . ?
C1 C5 C6 119.0(3) . . ?
C1 C5 C18 120.0(3) . . ?
C6 C5 C18 121.0(3) . . ?
C2 C6 C5 117.0(3) . . ?
C2 C6 C13 121.8(3) . . ?
C5 C6 C13 121.2(3) . . ?
C8 C7 N1 121.0(3) . . ?
C16 C7 N1 121.2(3) . . ?
C16 C7 C8 117.7(3) . . ?
C7 C8 S1 118.8(3) . . ?
C17 C8 S1 120.0(3) . . ?
C17 C8 C7 120.9(4) . . ?
C1 C9 C10 120.1(3) . . ?
C4 C9 C1 118.4(3) . . ?
C4 C9 C10 121.5(3) . . ?
C20 C11 C3 120.8(4) . . ?
C3 C12 S1 118.4(3) . . ?
C14 C12 S1 120.2(3) . . ?
C14 C12 C3 121.2(4) . . ?
C19 C14 C12 120.2(4) . . ?
C21 C16 C7 120.3(4) . . ?
C22 C17 C8 119.9(4) . . ?
C14 C19 C20 119.0(4) . . ?
C11 C20 C19 121.3(4) . . ?
C22 C21 C16 121.2(5) . . ?
C17 C22 C21 119.8(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
