# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_210831fyj_2_0m
_database_code_depnum_ccdc_archive 'CCDC 2376474'
loop_
_audit_author_name
_audit_author_address
'Jie Yu'
;Anhui Agricultural University
China
;
_audit_update_record             
;
2024-08-08 deposited with the CCDC.	2025-01-15 downloaded from the CCDC.
;
_audit_creation_date             2021-08-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H24 Br N O2 S'
_chemical_formula_sum            'C24 H24 Br N O2 S'
_chemical_formula_weight         470.41
_chemical_absolute_configuration rmad
_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 0.0148 0.0070 '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 -0.9502 1.0410 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2924 0.4247 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.8681(2)
_cell_length_b                   10.6446(2)
_cell_length_c                   21.1836(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2225.17(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9869
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      54.96
_cell_measurement_theta_min      3.63
_shelx_estimated_absorpt_T_max   0.890
_shelx_estimated_absorpt_T_min   0.831
_exptl_absorpt_coefficient_mu    2.397
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4355
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.2054 before and 0.0980 after correction. The Ratio of minimum to maximum transmission is 0.5800. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0871
_diffrn_reflns_av_unetI/netI     0.0537
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            23732
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.978
_diffrn_reflns_theta_min         3.631
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                3884
_reflns_number_total             4220
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.774
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 
;
 Flack x determined using 1525 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.021(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0383
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0520P)²+0.0224P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.0966
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C19(H19), C20(H20), C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_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 0.44991(5) 0.66174(4) 0.43687(2) 0.05860(17) Uani 1 1 d . . . . .
S1 S 0.52746(10) 0.74070(8) 0.63030(4) 0.0447(2) Uani 1 1 d . . . . .
O1 O 0.6478(3) 0.6742(3) 0.64650(14) 0.0590(7) Uani 1 1 d . . . . .
O2 O 0.5359(3) 0.8556(2) 0.59512(13) 0.0601(7) Uani 1 1 d . . . . .
N1 N 0.4363(3) 0.6450(3) 0.58863(13) 0.0410(7) Uani 1 1 d . . . . .
C1 C 0.3116(4) 0.6868(3) 0.55638(15) 0.0385(7) Uani 1 1 d . . . . .
H1 H 0.260251 0.741607 0.584874 0.046 Uiso 1 1 calc R . . . .
C2 C 0.2325(4) 0.5636(3) 0.54694(17) 0.0432(8) Uani 1 1 d . . . . .
H2A H 0.135828 0.578157 0.550901 0.052 Uiso 1 1 calc R . . . .
H2B H 0.250575 0.528672 0.505493 0.052 Uiso 1 1 calc R . . . .
C3 C 0.2820(4) 0.4738(3) 0.59882(16) 0.0392(8) Uani 1 1 d . . . . .
C4 C 0.4325(4) 0.5093(3) 0.60282(17) 0.0412(8) Uani 1 1 d . . . . .
H4A H 0.468018 0.492711 0.644696 0.049 Uiso 1 1 calc R . . . .
H4B H 0.485245 0.462291 0.572230 0.049 Uiso 1 1 calc R . . . .
C5 C 0.3384(4) 0.7568(4) 0.49505(17) 0.0474(9) Uani 1 1 d . . . . .
H5A H 0.383124 0.835712 0.504551 0.057 Uiso 1 1 calc R . . . .
H5B H 0.252602 0.775961 0.474929 0.057 Uiso 1 1 calc R . . . .
C6 C 0.2602(4) 0.3364(3) 0.57935(16) 0.0439(8) Uani 1 1 d . . . . .
C7 C 0.1325(5) 0.2972(4) 0.5613(2) 0.0551(10) Uani 1 1 d . . . . .
H7 H 0.061838 0.354912 0.560032 0.066 Uiso 1 1 calc R . . . .
C8 C 0.1081(5) 0.1728(4) 0.5452(2) 0.0674(12) Uani 1 1 d . . . . .
H8 H 0.021263 0.147398 0.533913 0.081 Uiso 1 1 calc R . . . .
C9 C 0.2119(6) 0.0879(4) 0.5458(2) 0.0700(14) Uani 1 1 d . . . . .
H9 H 0.196052 0.004847 0.534335 0.084 Uiso 1 1 calc R . . . .
C10 C 0.3386(5) 0.1249(4) 0.5631(3) 0.0694(13) Uani 1 1 d . . . . .
H10 H 0.409030 0.066842 0.563713 0.083 Uiso 1 1 calc R . . . .
C11 C 0.3633(5) 0.2488(4) 0.5799(2) 0.0596(11) Uani 1 1 d . . . . .
H11 H 0.450189 0.273086 0.591692 0.072 Uiso 1 1 calc R . . . .
C12 C 0.2111(4) 0.4932(3) 0.66315(16) 0.0408(8) Uani 1 1 d . . . . .
C13 C 0.2434(4) 0.4141(4) 0.71324(19) 0.0529(10) Uani 1 1 d . . . . .
H13 H 0.308725 0.352063 0.707832 0.063 Uiso 1 1 calc R . . . .
C14 C 0.1796(5) 0.4266(5) 0.7707(2) 0.0658(12) Uani 1 1 d . . . . .
H14 H 0.200894 0.371989 0.803530 0.079 Uiso 1 1 calc R . . . .
C15 C 0.0847(5) 0.5191(5) 0.7799(2) 0.0677(13) Uani 1 1 d . . . . .
H15 H 0.042383 0.527232 0.818936 0.081 Uiso 1 1 calc R . . . .
C16 C 0.0528(6) 0.5984(5) 0.7324(2) 0.0665(12) Uani 1 1 d . . . . .
H16 H -0.011183 0.661271 0.738755 0.080 Uiso 1 1 calc R . . . .
C17 C 0.1162(4) 0.5859(4) 0.6737(2) 0.0544(10) Uani 1 1 d . . . . .
H17 H 0.094021 0.641019 0.641226 0.065 Uiso 1 1 calc R . . . .
C18 C 0.4383(4) 0.7732(4) 0.70048(17) 0.0482(9) Uani 1 1 d . . . . .
C19 C 0.4448(5) 0.6894(5) 0.74954(18) 0.0638(11) Uani 1 1 d . . . . .
H19 H 0.499203 0.618285 0.746850 0.077 Uiso 1 1 calc R . . . .
C20 C 0.3681(6) 0.7131(7) 0.8037(2) 0.0825(18) Uani 1 1 d . . . . .
H20 H 0.369983 0.656264 0.836994 0.099 Uiso 1 1 calc R . . . .
C21 C 0.2889(6) 0.8206(8) 0.8083(3) 0.092(2) Uani 1 1 d . . . . .
C22 C 0.2859(6) 0.9016(6) 0.7588(3) 0.0866(18) Uani 1 1 d . . . . .
H22 H 0.233351 0.973964 0.761562 0.104 Uiso 1 1 calc R . . . .
C23 C 0.3587(5) 0.8791(5) 0.7048(2) 0.0690(13) Uani 1 1 d . . . . .
H23 H 0.354232 0.935102 0.671143 0.083 Uiso 1 1 calc R . . . .
C24 C 0.2043(9) 0.8412(10) 0.8680(3) 0.148(4) Uani 1 1 d . . . . .
H24A H 0.218508 0.925019 0.883309 0.222 Uiso 1 1 calc GR . . . .
H24B H 0.231326 0.781899 0.899708 0.222 Uiso 1 1 calc GR . . . .
H24C H 0.110127 0.829548 0.858286 0.222 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 C5 1.937(4) . ?
S1 O1 1.425(3) . ?
S1 O2 1.434(3) . ?
S1 N1 1.620(3) . ?
S1 C18 1.762(4) . ?
N1 C1 1.477(5) . ?
N1 C4 1.476(4) . ?
C1 H1 0.9800 . ?
C1 C2 1.540(5) . ?
C1 C5 1.521(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.536(5) . ?
C3 C4 1.535(5) . ?
C3 C6 1.535(5) . ?
C3 C12 1.546(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.381(6) . ?
C6 C11 1.380(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.388(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.366(7) . ?
C9 H9 0.9300 . ?
C9 C10 1.361(8) . ?
C10 H10 0.9300 . ?
C10 C11 1.387(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.392(5) . ?
C12 C17 1.378(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.377(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.372(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.351(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.399(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.371(6) . ?
C18 C23 1.377(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.397(7) . ?
C20 H20 0.9300 . ?
C20 C21 1.389(9) . ?
C21 C22 1.358(9) . ?
C21 C24 1.531(8) . ?
C22 H22 0.9300 . ?
C22 C23 1.373(7) . ?
C23 H23 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

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 120.05(19) . . ?
O1 S1 N1 106.35(16) . . ?
O1 S1 C18 108.08(19) . . ?
O2 S1 N1 106.56(16) . . ?
O2 S1 C18 107.46(19) . . ?
N1 S1 C18 107.82(17) . . ?
C1 N1 S1 121.7(2) . . ?
C4 N1 S1 121.2(2) . . ?
C4 N1 C1 111.6(3) . . ?
N1 C1 H1 109.0 . . ?
N1 C1 C2 103.0(3) . . ?
N1 C1 C5 113.4(3) . . ?
C2 C1 H1 109.0 . . ?
C5 C1 H1 109.0 . . ?
C5 C1 C2 113.2(3) . . ?
C1 C2 H2A 110.5 . . ?
C1 C2 H2B 110.5 . . ?
H2A C2 H2B 108.7 . . ?
C3 C2 C1 106.0(3) . . ?
C3 C2 H2A 110.5 . . ?
C3 C2 H2B 110.5 . . ?
C2 C3 C12 113.8(3) . . ?
C4 C3 C2 101.2(3) . . ?
C4 C3 C12 110.9(3) . . ?
C6 C3 C2 110.8(3) . . ?
C6 C3 C4 112.7(3) . . ?
C6 C3 C12 107.5(3) . . ?
N1 C4 C3 104.8(3) . . ?
N1 C4 H4A 110.8 . . ?
N1 C4 H4B 110.8 . . ?
C3 C4 H4A 110.8 . . ?
C3 C4 H4B 110.8 . . ?
H4A C4 H4B 108.9 . . ?
Br1 C5 H5A 109.0 . . ?
Br1 C5 H5B 109.0 . . ?
C1 C5 Br1 112.8(3) . . ?
C1 C5 H5A 109.0 . . ?
C1 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C7 C6 C3 119.4(3) . . ?
C7 C6 C11 118.1(4) . . ?
C11 C6 C3 122.5(4) . . ?
C6 C7 H7 119.5 . . ?
C6 C7 C8 121.0(4) . . ?
C8 C7 H7 119.5 . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 119.9(5) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0(4) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C11 120.3(4) . . ?
C11 C10 H10 119.8 . . ?
C6 C11 C10 120.7(4) . . ?
C6 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C13 C12 C3 119.2(3) . . ?
C17 C12 C3 123.1(3) . . ?
C17 C12 C13 117.7(4) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.7(4) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.4(4) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.1(4) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 119.9(4) . . ?
C17 C16 H16 120.0 . . ?
C12 C17 C16 121.0(4) . . ?
C12 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C19 C18 S1 119.3(4) . . ?
C19 C18 C23 120.6(4) . . ?
C23 C18 S1 120.1(3) . . ?
C18 C19 H19 120.7 . . ?
C18 C19 C20 118.7(5) . . ?
C20 C19 H19 120.7 . . ?
C19 C20 H20 119.6 . . ?
C21 C20 C19 120.7(5) . . ?
C21 C20 H20 119.6 . . ?
C20 C21 C24 118.9(8) . . ?
C22 C21 C20 118.8(5) . . ?
C22 C21 C24 122.3(8) . . ?
C21 C22 H22 119.3 . . ?
C21 C22 C23 121.4(6) . . ?
C23 C22 H22 119.3 . . ?
C18 C23 H23 120.1 . . ?
C22 C23 C18 119.8(5) . . ?
C22 C23 H23 120.1 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_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_219831fyj_1
_database_code_depnum_ccdc_archive 'CCDC 2376476'
loop_
_audit_author_name
_audit_author_address
'Jie Yu'
;Anhui Agricultural University
China
;
_audit_update_record             
;
2024-08-08 deposited with the CCDC.	2025-01-15 downloaded from the CCDC.
;
_audit_creation_date             2021-09-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H17 Cl N2 O4 S'
_chemical_formula_sum            'C13 H17 Cl N2 O4 S'
_chemical_formula_weight         332.79
_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 0.0148 0.0070 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3294 0.5404 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2925 0.4295 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   22.112(7)
_cell_length_b                   5.910(2)
_cell_length_c                   12.384(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.404(17)
_cell_angle_gamma                90
_cell_volume                     1574.4(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4114
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      54.02
_cell_measurement_theta_min      3.58
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.836
_exptl_absorpt_coefficient_mu    2.322
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4185
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1833 before and 0.0885 after correction. The Ratio of minimum to maximum transmission is 0.5574. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0778
_diffrn_reflns_av_unetI/netI     0.0577
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12569
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.975
_diffrn_reflns_theta_min         3.575
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1791
_reflns_number_total             2911
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2911
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1195
_refine_ls_R_factor_gt           0.0757
_refine_ls_restrained_S_all      1.094
_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)+(0.1159P)²+0.8082P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2055
_refine_ls_wR_factor_ref         0.2448
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C13(H13)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.90187(8) 0.4547(4) 0.44645(15) 0.1389(9) Uani 1 1 d . . . . .
S1 S 0.70963(5) 0.16926(19) 0.53921(8) 0.0638(4) Uani 1 1 d . . . . .
O1 O 0.72995(15) 0.0535(5) 0.4525(2) 0.0753(9) Uani 1 1 d . . . . .
O2 O 0.68414(15) 0.0464(6) 0.6175(2) 0.0810(10) Uani 1 1 d . . . . .
O3 O 0.54853(19) 1.0091(7) 0.2552(4) 0.1067(13) Uani 1 1 d . . . . .
O4 O 0.4961(2) 0.9637(8) 0.3789(3) 0.1118(15) Uani 1 1 d . . . . .
N1 N 0.76966(16) 0.3057(6) 0.6109(3) 0.0660(10) Uani 1 1 d . . . . .
N2 N 0.5385(2) 0.9145(8) 0.3361(3) 0.0799(11) Uani 1 1 d . . . . .
C1 C 0.7636(3) 0.4212(12) 0.7146(4) 0.0990(18) Uani 1 1 d . . . . .
H1A H 0.723654 0.496453 0.704017 0.119 Uiso 1 1 calc R . . . .
H1B H 0.767730 0.313923 0.775110 0.119 Uiso 1 1 calc R . . . .
C2 C 0.8143(4) 0.5853(14) 0.7371(7) 0.136(3) Uani 1 1 d . . . . .
H2A H 0.851350 0.518818 0.783745 0.163 Uiso 1 1 calc R . . . .
H2B H 0.802748 0.717127 0.774542 0.163 Uiso 1 1 calc R . . . .
C3 C 0.8253(3) 0.6485(9) 0.6285(7) 0.114(2) Uani 1 1 d . . . . .
H3A H 0.868453 0.690498 0.635784 0.136 Uiso 1 1 calc R . . . .
H3B H 0.799282 0.775822 0.597668 0.136 Uiso 1 1 calc R . . . .
C4 C 0.8091(2) 0.4409(9) 0.5531(4) 0.0766(13) Uani 1 1 d . . . . .
H4 H 0.784186 0.488675 0.480561 0.092 Uiso 1 1 calc R . . . .
C5 C 0.8637(2) 0.2995(10) 0.5366(4) 0.0812(14) Uani 1 1 d . . . . .
H5 H 0.846697 0.161012 0.497571 0.097 Uiso 1 1 calc R . . . .
C6 C 0.9104(2) 0.2293(11) 0.6414(5) 0.0958(16) Uani 1 1 d . . . . .
H6A H 0.928011 0.364920 0.680504 0.115 Uiso 1 1 calc R . . . .
H6B H 0.888526 0.148851 0.688969 0.115 Uiso 1 1 calc R . . . .
C7 C 0.9630(3) 0.0824(14) 0.6238(8) 0.146(3) Uani 1 1 d . . . . .
H7A H 0.946497 -0.039238 0.574320 0.219 Uiso 1 1 calc GR . . . .
H7B H 0.985005 0.021523 0.693746 0.219 Uiso 1 1 calc GR . . . .
H7C H 0.990838 0.171270 0.592171 0.219 Uiso 1 1 calc GR . . . .
C8 C 0.65473(19) 0.3747(7) 0.4761(3) 0.0587(10) Uani 1 1 d . . . . .
C9 C 0.6573(2) 0.4604(8) 0.3716(3) 0.0653(11) Uani 1 1 d . . . . .
H9 H 0.684826 0.398728 0.333079 0.078 Uiso 1 1 calc R . . . .
C10 C 0.6188(2) 0.6366(9) 0.3264(3) 0.0688(12) Uani 1 1 d . . . . .
H10 H 0.620400 0.696247 0.257621 0.083 Uiso 1 1 calc R . . . .
C11 C 0.5785(2) 0.7221(8) 0.3841(3) 0.0628(11) Uani 1 1 d . . . . .
C12 C 0.5740(2) 0.6363(8) 0.4861(4) 0.0706(12) Uani 1 1 d . . . . .
H12 H 0.545365 0.695790 0.522841 0.085 Uiso 1 1 calc R . . . .
C13 C 0.6125(2) 0.4622(8) 0.5320(3) 0.0667(12) Uani 1 1 d . . . . .
H13 H 0.610221 0.402934 0.600544 0.080 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
Cl1 C5 1.800(5) . ?
S1 O1 1.430(3) . ?
S1 O2 1.428(3) . ?
S1 N1 1.629(4) . ?
S1 C8 1.766(4) . ?
O3 N2 1.213(5) . ?
O4 N2 1.213(5) . ?
N1 C1 1.487(6) . ?
N1 C4 1.483(6) . ?
N2 C11 1.479(6) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.459(9) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.471(9) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.533(8) . ?
C4 H4 0.9800 . ?
C4 C5 1.520(7) . ?
C5 H5 0.9800 . ?
C5 C6 1.518(7) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.505(9) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.403(5) . ?
C8 C13 1.385(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.379(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.363(6) . ?
C11 C12 1.386(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.372(6) . ?
C13 H13 0.9300 . ?

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 N1 106.73(19) . . ?
O1 S1 C8 107.45(17) . . ?
O2 S1 O1 120.6(2) . . ?
O2 S1 N1 106.35(19) . . ?
O2 S1 C8 108.14(19) . . ?
N1 S1 C8 106.9(2) . . ?
C1 N1 S1 118.2(3) . . ?
C4 N1 S1 119.9(3) . . ?
C4 N1 C1 110.5(4) . . ?
O3 N2 O4 123.9(5) . . ?
O3 N2 C11 118.7(4) . . ?
O4 N2 C11 117.4(4) . . ?
N1 C1 H1A 110.8 . . ?
N1 C1 H1B 110.8 . . ?
H1A C1 H1B 108.9 . . ?
C2 C1 N1 104.6(5) . . ?
C2 C1 H1A 110.8 . . ?
C2 C1 H1B 110.8 . . ?
C1 C2 H2A 110.5 . . ?
C1 C2 H2B 110.5 . . ?
C1 C2 C3 106.0(6) . . ?
H2A C2 H2B 108.7 . . ?
C3 C2 H2A 110.5 . . ?
C3 C2 H2B 110.5 . . ?
C2 C3 H3A 110.4 . . ?
C2 C3 H3B 110.4 . . ?
C2 C3 C4 106.8(5) . . ?
H3A C3 H3B 108.6 . . ?
C4 C3 H3A 110.4 . . ?
C4 C3 H3B 110.4 . . ?
N1 C4 C3 102.6(4) . . ?
N1 C4 H4 109.3 . . ?
N1 C4 C5 110.0(4) . . ?
C3 C4 H4 109.3 . . ?
C5 C4 C3 116.2(5) . . ?
C5 C4 H4 109.3 . . ?
Cl1 C5 H5 107.5 . . ?
C4 C5 Cl1 107.7(4) . . ?
C4 C5 H5 107.5 . . ?
C6 C5 Cl1 110.2(4) . . ?
C6 C5 C4 116.1(4) . . ?
C6 C5 H5 107.5 . . ?
C5 C6 H6A 108.4 . . ?
C5 C6 H6B 108.4 . . ?
H6A C6 H6B 107.5 . . ?
C7 C6 C5 115.5(6) . . ?
C7 C6 H6A 108.4 . . ?
C7 C6 H6B 108.4 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 S1 119.0(3) . . ?
C13 C8 S1 120.6(3) . . ?
C13 C8 C9 120.2(4) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.6(4) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 H10 120.5 . . ?
C11 C10 C9 119.0(4) . . ?
C11 C10 H10 120.5 . . ?
C10 C11 N2 118.6(4) . . ?
C10 C11 C12 122.4(4) . . ?
C12 C11 N2 119.0(4) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 C11 118.9(4) . . ?
C13 C12 H12 120.6 . . ?
C8 C13 H13 120.1 . . ?
C12 C13 C8 119.9(4) . . ?
C12 C13 H13 120.1 . . ?

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

data_210713fyj
_database_code_depnum_ccdc_archive 'CCDC 2376580'
loop_
_audit_author_name
_audit_author_address
'Jie Yu'
;Anhui Agricultural University
China
;
_audit_update_record             
;
2024-08-09 deposited with the CCDC.	2025-01-15 downloaded from the CCDC.
;
_audit_creation_date             2024-08-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H17 Br N2 O4 S'
_chemical_formula_sum            'C13 H17 Br N2 O4 S'
_chemical_formula_weight         377.25
_chemical_absolute_configuration rmad
_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      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   12.403(11)
_cell_length_b                   5.914(4)
_cell_length_c                   22.599(16)
_cell_angle_alpha                90
_cell_angle_beta                 104.87(2)
_cell_angle_gamma                90
_cell_volume                     1602(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    744
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      19.085
_cell_measurement_theta_min      2.797
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.687
_exptl_absorpt_coefficient_mu    2.712
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1283 before and 0.0580 after correction.
The Ratio of minimum to maximum transmission is 0.5491.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1062
_diffrn_reflns_av_unetI/netI     0.1727
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            5439
_diffrn_reflns_point_group_measured_fraction_full 0.845
_diffrn_reflns_point_group_measured_fraction_max 0.846
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.675
_diffrn_reflns_theta_min         2.798
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.967
_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           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.584
_reflns_Friedel_fraction_full    0.696
_reflns_Friedel_fraction_max     0.696
_reflns_number_gt                1263
_reflns_number_total             2581
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.907
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.101
_refine_ls_abs_structure_details 
;
 Flack x determined using 289 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2581
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.1754
_refine_ls_R_factor_gt           0.0782
_refine_ls_restrained_S_all      0.974
_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)+(0.0948P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1750
_refine_ls_wR_factor_ref         0.2212
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C2 \\sim C3 \\sim C4 \\sim C5: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
3.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
3.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C13(H13)
3.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.53702(17) 0.5478(5) 0.09648(9) 0.0935(9) Uani 1 1 d . . . . .
S1 S 0.4635(3) 0.8595(6) 0.29269(17) 0.0480(10) Uani 1 1 d . . . . .
O1 O 0.5494(9) 0.9759(17) 0.2719(5) 0.068(3) Uani 1 1 d . . . . .
O2 O 0.3857(8) 0.9853(16) 0.3198(5) 0.062(3) Uani 1 1 d . . . . .
O3 O 0.7580(11) 0.022(3) 0.4479(6) 0.080(4) Uani 1 1 d . . . . .
O4 O 0.6235(11) 0.020(3) 0.4916(6) 0.093(4) Uani 1 1 d . . . . .
N1 N 0.3857(9) 0.7385(19) 0.2351(4) 0.041(3) Uani 1 1 d . . . . .
N2 N 0.6749(12) 0.103(2) 0.4551(6) 0.063(4) Uani 1 1 d . . . . .
C1 C 0.4486(14) 0.733(3) 0.1378(7) 0.061(4) Uani 1 1 d . . . . .
H1 H 0.4921 0.8682 0.1535 0.074 Uiso 1 1 calc R U . . .
C2 C 0.4338(11) 0.593(3) 0.1938(6) 0.052(4) Uani 1 1 d . U . . .
H2 H 0.5083 0.5458 0.2172 0.062 Uiso 1 1 calc R U . . .
C3 C 0.3613(15) 0.383(3) 0.1814(9) 0.075(4) Uani 1 1 d . U . . .
H3A H 0.3925 0.2621 0.2097 0.090 Uiso 1 1 calc R U . . .
H3B H 0.3517 0.3296 0.1398 0.090 Uiso 1 1 calc R U . . .
C4 C 0.2480(18) 0.471(4) 0.1921(12) 0.093(5) Uani 1 1 d . U . . .
H4A H 0.2034 0.5447 0.1557 0.112 Uiso 1 1 calc R U . . .
H4B H 0.2052 0.3472 0.2029 0.112 Uiso 1 1 calc R U . . .
C5 C 0.2797(14) 0.625(3) 0.2406(9) 0.077(5) Uani 1 1 d . U . . .
H5A H 0.2923 0.5465 0.2795 0.093 Uiso 1 1 calc R U . . .
H5B H 0.2215 0.7364 0.2384 0.093 Uiso 1 1 calc R U . . .
C6 C 0.3383(12) 0.809(3) 0.0969(6) 0.058(4) Uani 1 1 d . . . . .
H6A H 0.2931 0.6767 0.0819 0.069 Uiso 1 1 calc R U . . .
H6B H 0.2990 0.8980 0.1208 0.069 Uiso 1 1 calc R U . . .
C7 C 0.352(2) 0.945(4) 0.0439(7) 0.096(8) Uani 1 1 d . . . . .
H7A H 0.3536 0.8463 0.0105 0.144 Uiso 1 1 calc R U . . .
H7B H 0.4202 1.0291 0.0556 0.144 Uiso 1 1 calc R U . . .
H7C H 0.2902 1.0479 0.0315 0.144 Uiso 1 1 calc R U . . .
C8 C 0.5277(11) 0.648(2) 0.3443(5) 0.041(3) Uani 1 1 d . . . . .
C9 C 0.6308(12) 0.581(3) 0.3454(7) 0.056(4) Uani 1 1 d . . . . .
H9 H 0.6690 0.6549 0.3207 0.067 Uiso 1 1 calc R U . . .
C10 C 0.6835(14) 0.403(3) 0.3822(7) 0.062(5) Uani 1 1 d . . . . .
H10 H 0.7555 0.3579 0.3827 0.074 Uiso 1 1 calc R U . . .
C11 C 0.6231(13) 0.299(2) 0.4176(6) 0.046(4) Uani 1 1 d . . . . .
C12 C 0.5178(13) 0.361(3) 0.4181(6) 0.058(4) Uani 1 1 d . . . . .
H12 H 0.4793 0.2837 0.4421 0.070 Uiso 1 1 calc R U . . .
C13 C 0.4682(12) 0.546(4) 0.3809(7) 0.060(4) Uani 1 1 d . . . . .
H13 H 0.3975 0.5976 0.3813 0.072 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.949(14) . ?
S1 O1 1.444(10) . ?
S1 O2 1.471(10) . ?
S1 N1 1.578(12) . ?
S1 C8 1.756(14) . ?
O3 N2 1.184(16) . ?
O4 N2 1.263(16) . ?
N1 C2 1.501(17) . ?
N1 C5 1.51(2) . ?
N2 C11 1.485(19) . ?
C1 H1 0.9800 . ?
C1 C2 1.56(2) . ?
C1 C6 1.51(2) . ?
C2 H2 0.9800 . ?
C2 C3 1.52(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.57(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.40(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.49(2) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.334(18) . ?
C8 C13 1.380(19) . ?
C9 H9 0.9300 . ?
C9 C10 1.39(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.38(2) . ?
C11 C12 1.36(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.42(2) . ?
C13 H13 0.9300 . ?

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 120.8(6) . . ?
O1 S1 N1 107.1(6) . . ?
O1 S1 C8 108.1(6) . . ?
O2 S1 N1 104.2(6) . . ?
O2 S1 C8 108.5(6) . . ?
N1 S1 C8 107.5(7) . . ?
C2 N1 S1 121.1(9) . . ?
C2 N1 C5 106.8(11) . . ?
C5 N1 S1 119.7(9) . . ?
O3 N2 O4 122.5(14) . . ?
O3 N2 C11 120.2(15) . . ?
O4 N2 C11 117.2(14) . . ?
Br1 C1 H1 107.9 . . ?
C2 C1 Br1 106.8(10) . . ?
C2 C1 H1 107.9 . . ?
C6 C1 Br1 114.0(11) . . ?
C6 C1 H1 107.9 . . ?
C6 C1 C2 112.2(13) . . ?
N1 C2 C1 110.4(11) . . ?
N1 C2 H2 107.3 . . ?
N1 C2 C3 105.8(11) . . ?
C1 C2 H2 107.3 . . ?
C3 C2 C1 118.1(14) . . ?
C3 C2 H2 107.3 . . ?
C2 C3 H3A 111.3 . . ?
C2 C3 H3B 111.3 . . ?
C2 C3 C4 102.2(14) . . ?
H3A C3 H3B 109.2 . . ?
C4 C3 H3A 111.3 . . ?
C4 C3 H3B 111.3 . . ?
C3 C4 H4A 110.8 . . ?
C3 C4 H4B 110.8 . . ?
H4A C4 H4B 108.9 . . ?
C5 C4 C3 104.6(18) . . ?
C5 C4 H4A 110.8 . . ?
C5 C4 H4B 110.8 . . ?
N1 C5 H5A 110.2 . . ?
N1 C5 H5B 110.2 . . ?
C4 C5 N1 107.5(14) . . ?
C4 C5 H5A 110.2 . . ?
C4 C5 H5B 110.2 . . ?
H5A C5 H5B 108.5 . . ?
C1 C6 H6A 109.1 . . ?
C1 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
C7 C6 C1 112.5(15) . . ?
C7 C6 H6A 109.1 . . ?
C7 C6 H6B 109.1 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 S1 119.6(11) . . ?
C9 C8 C13 121.1(13) . . ?
C13 C8 S1 119.2(10) . . ?
C8 C9 H9 118.8 . . ?
C8 C9 C10 122.5(15) . . ?
C10 C9 H9 118.8 . . ?
C9 C10 H10 121.9 . . ?
C11 C10 C9 116.3(14) . . ?
C11 C10 H10 121.9 . . ?
C10 C11 N2 117.5(14) . . ?
C12 C11 N2 118.8(14) . . ?
C12 C11 C10 123.6(14) . . ?
C11 C12 H12 120.9 . . ?
C11 C12 C13 118.2(14) . . ?
C13 C12 H12 120.9 . . ?
C8 C13 C12 118.3(12) . . ?
C8 C13 H13 120.9 . . ?
C12 C13 H13 120.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C1 C2 N1 169.2(9) . . . . ?
Br1 C1 C2 C3 -68.9(16) . . . . ?
Br1 C1 C6 C7 -59.4(18) . . . . ?
S1 N1 C2 C1 -95.3(13) . . . . ?
S1 N1 C2 C3 135.8(11) . . . . ?
S1 N1 C5 C4 -160.2(13) . . . . ?
S1 C8 C9 C10 -175.5(13) . . . . ?
S1 C8 C13 C12 174.1(13) . . . . ?
O1 S1 N1 C2 50.2(11) . . . . ?
O1 S1 N1 C5 -172.8(11) . . . . ?
O1 S1 C8 C9 -17.5(14) . . . . ?
O1 S1 C8 C13 165.7(12) . . . . ?
O2 S1 N1 C2 179.2(10) . . . . ?
O2 S1 N1 C5 -43.7(12) . . . . ?
O2 S1 C8 C9 -150.0(12) . . . . ?
O2 S1 C8 C13 33.1(15) . . . . ?
O3 N2 C11 C10 -10(2) . . . . ?
O3 N2 C11 C12 167.4(16) . . . . ?
O4 N2 C11 C10 173.8(15) . . . . ?
O4 N2 C11 C12 -9(2) . . . . ?
N1 S1 C8 C9 97.8(13) . . . . ?
N1 S1 C8 C13 -79.1(14) . . . . ?
N1 C2 C3 C4 24.6(18) . . . . ?
N2 C11 C12 C13 -178.5(15) . . . . ?
C1 C2 C3 C4 -99.7(18) . . . . ?
C2 N1 C5 C4 -17.8(18) . . . . ?
C2 C1 C6 C7 179.1(14) . . . . ?
C2 C3 C4 C5 -36(2) . . . . ?
C3 C4 C5 N1 33.3(19) . . . . ?
C5 N1 C2 C1 122.9(14) . . . . ?
C5 N1 C2 C3 -6.1(16) . . . . ?
C6 C1 C2 N1 -65.2(17) . . . . ?
C6 C1 C2 C3 56.7(18) . . . . ?
C8 S1 N1 C2 -65.8(11) . . . . ?
C8 S1 N1 C5 71.3(12) . . . . ?
C8 C9 C10 C11 0(2) . . . . ?
C9 C8 C13 C12 -3(3) . . . . ?
C9 C10 C11 N2 177.1(13) . . . . ?
C9 C10 C11 C12 0(2) . . . . ?
C10 C11 C12 C13 -1(3) . . . . ?
C11 C12 C13 C8 3(3) . . . . ?
C13 C8 C9 C10 1(2) . . . . ?

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

data_211025fyj_0m
_database_code_depnum_ccdc_archive 'CCDC 2376475'
loop_
_audit_author_name
_audit_author_address
'Jie Yu'
;Anhui Agricultural University
China
;
_audit_update_record             
;
2024-08-08 deposited with the CCDC.	2025-01-15 downloaded from the CCDC.
;
_audit_creation_date             2021-10-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H17 Br N2 O4 S'
_chemical_formula_sum            'C13 H17 Br N2 O4 S'
_chemical_formula_weight         377.25
_chemical_absolute_configuration rmad
_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 0.0137 0.0067 '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 -0.9338 1.0006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2925 0.4295 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.0954(2)
_cell_length_b                   6.18390(10)
_cell_length_c                   13.3904(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.3620(10)
_cell_angle_gamma                90
_cell_volume                     802.09(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8251
_cell_measurement_temperature    296
_cell_measurement_theta_max      54.761
_cell_measurement_theta_min      2.993
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.644
_exptl_absorpt_coefficient_mu    3.212
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1407 before and 0.0702 after correction.
The Ratio of minimum to maximum transmission is 0.6517.
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    1.562
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12282
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.892
_diffrn_reflns_theta_min         2.992
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           2.86
_diffrn_source_power             0.1995708
_diffrn_source_voltage           69.78
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.811
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                2626
_reflns_number_total             3034
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 
;
 Flack x determined using 980 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.032(16)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3034
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0437
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0682P)²+0.3751P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1146
_refine_ls_wR_factor_ref         0.1239
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C13(H13)
2.d Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C)
;
_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 0.34411(9) 0.29818(17) 0.49026(5) 0.0878(3) Uani 1 1 d . . . . .
S1 S 0.57113(17) 0.1601(2) 0.20119(11) 0.0624(4) Uani 1 1 d . . . . .
O1 O 0.6047(6) 0.0079(8) 0.2847(4) 0.0836(15) Uani 1 1 d . . . . .
O2 O 0.5562(6) 0.0910(9) 0.0968(4) 0.0768(13) Uani 1 1 d . . . . .
O3 O 0.9897(9) 0.9982(17) 0.2401(8) 0.140(3) Uani 1 1 d . . . . .
O4 O 1.0534(10) 0.890(2) 0.3960(7) 0.177(5) Uani 1 1 d . . . . .
N1 N 0.4287(5) 0.2792(10) 0.2014(3) 0.0589(11) Uani 1 1 d . . . . .
N2 N 0.9841(8) 0.8754(15) 0.3083(7) 0.105(3) Uani 1 1 d . . . . .
C1 C 0.4085(6) 0.3682(10) 0.2999(4) 0.0594(15) Uani 1 1 d . . . . .
H1 H 0.497597 0.419313 0.344207 0.071 Uiso 1 1 calc R U . . .
C2 C 0.3141(9) 0.5641(14) 0.2626(6) 0.083(2) Uani 1 1 d . . . . .
H2A H 0.240349 0.566195 0.295918 0.099 Uiso 1 1 calc R U . . .
H2B H 0.366339 0.697285 0.279505 0.099 Uiso 1 1 calc R U . . .
C3 C 0.2549(7) 0.5420(10) 0.1453(5) 0.0607(14) Uani 1 1 d . . . . .
C4 C 0.3656(8) 0.4299(18) 0.1132(5) 0.090(2) Uani 1 1 d . . . . .
H4A H 0.433468 0.532310 0.103073 0.108 Uiso 1 1 calc R U . . .
H4B H 0.327959 0.350283 0.049016 0.108 Uiso 1 1 calc R U . . .
C5 C 0.2146(11) 0.7588(17) 0.0916(8) 0.110(3) Uani 1 1 d . . . . .
H5A H 0.292875 0.853881 0.108873 0.165 Uiso 1 1 calc R U . . .
H5B H 0.141084 0.821486 0.114392 0.165 Uiso 1 1 calc R U . . .
H5C H 0.184275 0.737674 0.017583 0.165 Uiso 1 1 calc R U . . .
C6 C 0.1264(8) 0.4007(18) 0.1173(8) 0.103(3) Uani 1 1 d . . . . .
H6A H 0.085285 0.403792 0.043351 0.155 Uiso 1 1 calc R U . . .
H6B H 0.061471 0.454293 0.151721 0.155 Uiso 1 1 calc R U . . .
H6C H 0.151241 0.254773 0.139175 0.155 Uiso 1 1 calc R U . . .
C7 C 0.3556(8) 0.1905(12) 0.3569(5) 0.0698(17) Uani 1 1 d . . . . .
H7A H 0.417567 0.067441 0.367509 0.084 Uiso 1 1 calc R U . . .
H7B H 0.265133 0.143470 0.315527 0.084 Uiso 1 1 calc R U . . .
C8 C 0.6988(6) 0.3643(10) 0.2308(5) 0.0611(16) Uani 1 1 d . . . . .
C9 C 0.7138(7) 0.5025(13) 0.1540(5) 0.0693(17) Uani 1 1 d . . . . .
H9 H 0.661915 0.481887 0.085307 0.083 Uiso 1 1 calc R U . . .
C10 C 0.8069(7) 0.6727(15) 0.1797(5) 0.0771(19) Uani 1 1 d . . . . .
H10 H 0.816268 0.770348 0.129302 0.092 Uiso 1 1 calc R U . . .
C11 C 0.8845(7) 0.6931(13) 0.2811(6) 0.0744(19) Uani 1 1 d . . . . .
C12 C 0.8746(7) 0.5542(17) 0.3580(6) 0.087(2) Uani 1 1 d . . . . .
H12 H 0.930458 0.572303 0.425750 0.104 Uiso 1 1 calc R U . . .
C13 C 0.7816(7) 0.3884(14) 0.3340(5) 0.075(2) Uani 1 1 d . . . . .
H13 H 0.773082 0.292491 0.385295 0.090 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C7 1.939(6) . ?
S1 O1 1.428(5) . ?
S1 O2 1.429(5) . ?
S1 N1 1.616(5) . ?
S1 C8 1.768(7) . ?
O3 N2 1.200(12) . ?
O4 N2 1.189(11) . ?
N1 C1 1.496(7) . ?
N1 C4 1.498(9) . ?
N2 C11 1.486(11) . ?
C1 H1 0.9800 . ?
C1 C2 1.535(10) . ?
C1 C7 1.518(9) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.521(10) . ?
C3 C4 1.479(10) . ?
C3 C5 1.521(12) . ?
C3 C6 1.521(10) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.379(9) . ?
C8 C13 1.406(9) . ?
C9 H9 0.9300 . ?
C9 C10 1.388(11) . ?
C10 H10 0.9300 . ?
C10 C11 1.369(10) . ?
C11 C12 1.366(12) . ?
C12 H12 0.9300 . ?
C12 C13 1.367(12) . ?
C13 H13 0.9300 . ?

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 120.4(3) . . ?
O1 S1 N1 108.3(3) . . ?
O1 S1 C8 107.3(3) . . ?
O2 S1 N1 106.8(3) . . ?
O2 S1 C8 107.6(3) . . ?
N1 S1 C8 105.5(3) . . ?
C1 N1 S1 120.8(4) . . ?
C1 N1 C4 109.5(5) . . ?
C4 N1 S1 117.6(4) . . ?
O3 N2 C11 117.8(8) . . ?
O4 N2 O3 124.2(10) . . ?
O4 N2 C11 118.0(10) . . ?
N1 C1 H1 108.8 . . ?
N1 C1 C2 103.3(5) . . ?
N1 C1 C7 109.4(5) . . ?
C2 C1 H1 108.8 . . ?
C7 C1 H1 108.8 . . ?
C7 C1 C2 117.4(6) . . ?
C1 C2 H2A 110.3 . . ?
C1 C2 H2B 110.3 . . ?
H2A C2 H2B 108.6 . . ?
C3 C2 C1 107.0(6) . . ?
C3 C2 H2A 110.3 . . ?
C3 C2 H2B 110.3 . . ?
C2 C3 C5 112.6(7) . . ?
C2 C3 C6 111.5(7) . . ?
C4 C3 C2 103.5(6) . . ?
C4 C3 C5 113.5(7) . . ?
C4 C3 C6 108.7(7) . . ?
C6 C3 C5 107.1(7) . . ?
N1 C4 H4A 110.8 . . ?
N1 C4 H4B 110.8 . . ?
C3 C4 N1 104.5(5) . . ?
C3 C4 H4A 110.8 . . ?
C3 C4 H4B 110.8 . . ?
H4A C4 H4B 108.9 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
Br1 C7 H7A 109.8 . . ?
Br1 C7 H7B 109.8 . . ?
C1 C7 Br1 109.6(4) . . ?
C1 C7 H7A 109.8 . . ?
C1 C7 H7B 109.8 . . ?
H7A C7 H7B 108.2 . . ?
C9 C8 S1 120.1(5) . . ?
C9 C8 C13 120.5(7) . . ?
C13 C8 S1 119.3(5) . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C10 119.6(6) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 H10 120.8 . . ?
C11 C10 C9 118.3(7) . . ?
C11 C10 H10 120.8 . . ?
C10 C11 N2 118.2(8) . . ?
C12 C11 N2 118.7(7) . . ?
C12 C11 C10 123.1(8) . . ?
C11 C12 H12 120.5 . . ?
C11 C12 C13 119.0(7) . . ?
C13 C12 H12 120.5 . . ?
C8 C13 H13 120.3 . . ?
C12 C13 C8 119.3(7) . . ?
C12 C13 H13 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
S1 N1 C1 C2 148.4(5) . . . . ?
S1 N1 C1 C7 -85.8(6) . . . . ?
S1 N1 C4 C3 -169.6(5) . . . . ?
S1 C8 C9 C10 175.0(5) . . . . ?
S1 C8 C13 C12 -176.2(6) . . . . ?
O1 S1 N1 C1 47.8(6) . . . . ?
O1 S1 N1 C4 -173.8(6) . . . . ?
O1 S1 C8 C9 163.6(5) . . . . ?
O1 S1 C8 C13 -18.4(6) . . . . ?
O2 S1 N1 C1 178.8(5) . . . . ?
O2 S1 N1 C4 -42.7(7) . . . . ?
O2 S1 C8 C9 32.8(6) . . . . ?
O2 S1 C8 C13 -149.2(5) . . . . ?
O3 N2 C11 C10 1.4(11) . . . . ?
O3 N2 C11 C12 -178.6(9) . . . . ?
O4 N2 C11 C10 -178.5(9) . . . . ?
O4 N2 C11 C12 1.5(13) . . . . ?
N1 S1 C8 C9 -81.0(5) . . . . ?
N1 S1 C8 C13 97.0(5) . . . . ?
N1 C1 C2 C3 14.9(8) . . . . ?
N1 C1 C7 Br1 175.2(4) . . . . ?
N2 C11 C12 C13 178.9(7) . . . . ?
C1 N1 C4 C3 -26.8(8) . . . . ?
C1 C2 C3 C4 -31.3(9) . . . . ?
C1 C2 C3 C5 -154.3(7) . . . . ?
C1 C2 C3 C6 85.3(8) . . . . ?
C2 C1 C7 Br1 -67.6(6) . . . . ?
C2 C3 C4 N1 34.8(8) . . . . ?
C4 N1 C1 C2 7.0(7) . . . . ?
C4 N1 C1 C7 132.8(6) . . . . ?
C5 C3 C4 N1 157.2(7) . . . . ?
C6 C3 C4 N1 -83.7(8) . . . . ?
C7 C1 C2 C3 -105.6(7) . . . . ?
C8 S1 N1 C1 -66.9(5) . . . . ?
C8 S1 N1 C4 71.6(6) . . . . ?
C8 C9 C10 C11 2.1(10) . . . . ?
C9 C8 C13 C12 1.8(10) . . . . ?
C9 C10 C11 N2 180.0(7) . . . . ?
C9 C10 C11 C12 0.0(11) . . . . ?
C10 C11 C12 C13 -1.1(12) . . . . ?
C11 C12 C13 C8 0.2(11) . . . . ?
C13 C8 C9 C10 -3.0(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
