# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# 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_g250219b_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2mdqnf
_database_code_depnum_ccdc_archive 'CCDC 2425305'
loop_
_audit_author_name
_audit_author_address
'Weijian Ye'
;suzhou 
China
;
_audit_update_record             
;
2025-02-19 deposited with the CCDC.	2025-08-15 downloaded from the CCDC.
;
_audit_creation_date             2025-02-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_chemical_formula_moiety         'C21 H24 Br N O3 S2'
_chemical_formula_sum            'C21 H24 Br N O3 S2'
_chemical_formula_weight         482.43
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
Br -0.38188 2.46625 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95570 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
C 0.00313 0.00162 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.01085 0.00610 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
S 0.12485 0.12449 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.86690 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   11.1305(18)
_cell_length_b                   17.689(2)
_cell_length_c                   12.4682(19)
_cell_angle_alpha                90
_cell_angle_beta                 112.645(18)
_cell_angle_gamma                90
_cell_volume                     2265.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    223.15
_cell_measurement_reflns_used    3260
_cell_measurement_theta_min      2.0700
_cell_measurement_theta_max      23.7340
_exptl_absorpt_coefficient_mu    2.019
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.72062
_exptl_absorpt_correction_T_max  1.00000
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_colour            colourless
_exptl_crystal_description       block
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_F_000             992.0
_diffrn_reflns_av_R_equivalents  0.0613
_diffrn_reflns_av_unetI/netI     0.0964
_diffrn_reflns_Laue_measured_fraction_full 1.0000
_diffrn_reflns_Laue_measured_fraction_max 0.8644
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13874
_diffrn_reflns_point_group_measured_fraction_full 1.0000
_diffrn_reflns_point_group_measured_fraction_max 0.8644
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         30.67
_diffrn_reflns_theta_min         2.09
_diffrn_ambient_temperature      223.15
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 0.8644
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -15
_reflns_limit_k_max              25
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              -8
_reflns_number_gt                2843
_reflns_number_total             6045
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.2994
_refine_diff_density_min         -1.2995
_refine_diff_density_rms         0.2237
_refine_ls_d_res_high            0.6968
_refine_ls_d_res_low             9.7523
_refine_ls_goodness_of_fit_ref   1.0382
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    38
_refine_ls_number_parameters     258
_refine_ls_number_reflns         6997
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1436
_refine_ls_R_factor_gt           0.0568
_refine_ls_restrained_S_all      1.0382
_refine_ls_shift/su_max          -0.0006
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0441P)²+0.3348P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1503
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C7(H7), C11(H11), C10(H10), C17(H17), C16(H16), C14(H14), C13(H13),
 N1(H1)
2.b Idealised Me refined as rotating group:
 C21(H21a,H21b,H21c), C5(H5a,H5b,H5c), C19(H19a,H19b,H19c), C20(H20a,H20b,
 H20c), C1(H1a,H1b,H1c)
;
_atom_sites_solution_primary     dual
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
Br1 Br 0.18320(5) 0.52275(3) 0.26773(4) 0.0910(2) Uani 1.000000 .
S2 S 0.96023(9) 0.76065(5) 0.56237(8) 0.0459(2) Uani 1.000000 .
S1 S 0.52580(11) 0.75882(7) 0.65613(10) 0.0720(4) Uani 1.000000 .
O3 O 0.9435(3) 0.83049(13) 0.5010(2) 0.0591(7) Uani 1.000000 .
O2 O 1.0878(2) 0.73687(14) 0.6363(2) 0.0618(7) Uani 1.000000 .
O1 O 0.8788(3) 0.67696(17) 0.8139(2) 0.0723(8) Uani 1.000000 .
N1 N 0.8809(3) 0.76232(16) 0.6496(2) 0.0465(7) Uani 1.000000 .
C15 C 0.7834(3) 0.57017(18) 0.3053(3) 0.0409(8) Uani 1.000000 .
C12 C 0.8865(3) 0.68838(18) 0.4632(3) 0.0412(8) Uani 1.000000 .
C4 C 0.7494(3) 0.7729(2) 0.6190(3) 0.0456(8) Uani 1.000000 .
C18 C 0.7251(3) 0.50449(19) 0.2202(3) 0.0452(8) Uani 1.000000 .
C14 C 0.8007(4) 0.6414(2) 0.2694(3) 0.0490(9) Uani 1.000000 .
C13 C 0.8501(4) 0.70031(19) 0.3457(3) 0.0505(9) Uani 1.000000 .
C3 C 0.6914(4) 0.7398(2) 0.6860(3) 0.0504(9) Uani 1.000000 .
C6 C 0.4401(4) 0.6894(2) 0.5515(3) 0.0527(9) Uani 1.000000 .
C10 C 0.2316(4) 0.6358(2) 0.4409(3) 0.0586(10) Uani 1.000000 .
C11 C 0.3077(4) 0.6848(2) 0.5248(3) 0.0543(10) Uani 1.000000 .
C17 C 0.8695(4) 0.6174(2) 0.5023(3) 0.0552(10) Uani 1.000000 .
C16 C 0.8183(4) 0.5598(2) 0.4245(3) 0.0549(10) Uani 1.000000 .
C9 C 0.2879(4) 0.5907(2) 0.3843(3) 0.0574(10) Uani 1.000000 .
C2 C 0.7617(5) 0.6891(2) 0.7834(3) 0.0612(11) Uani 1.000000 .
C7 C 0.4949(4) 0.6437(2) 0.4945(4) 0.0691(12) Uani 1.000000 .
C21 C 0.7074(4) 0.5243(2) 0.0966(3) 0.0659(12) Uani 1.000000 .
C8 C 0.4192(4) 0.5940(2) 0.4109(4) 0.0698(12) Uani 1.000000 .
C5 C 0.6790(4) 0.8197(2) 0.5142(3) 0.0686(12) Uani 1.000000 .
C19 C 0.8149(4) 0.4352(2) 0.2575(3) 0.0668(12) Uani 1.000000 .
C20 C 0.5921(4) 0.4847(3) 0.2218(4) 0.0767(13) Uani 1.000000 .
C1 C 0.6892(5) 0.6487(3) 0.8460(4) 0.0948(17) Uani 1.000000 .
H8 H 0.4574(4) 0.5624(2) 0.3722(4) 0.0838(14) Uiso 1.000000 R
H7 H 0.5849(4) 0.6462(2) 0.5125(4) 0.0829(14) Uiso 1.000000 R
H11 H 0.2695(4) 0.7155(2) 0.5645(3) 0.0651(12) Uiso 1.000000 R
H10 H 0.1415(4) 0.6334(2) 0.4223(3) 0.0704(12) Uiso 1.000000 R
H17 H 0.8932(4) 0.6088(2) 0.5823(3) 0.0662(12) Uiso 1.000000 R
H16 H 0.8064(4) 0.5121(2) 0.4521(3) 0.0659(12) Uiso 1.000000 R
H14 H 0.7778(4) 0.6502(2) 0.1896(3) 0.0588(11) Uiso 1.000000 R
H13 H 0.8590(4) 0.74849(19) 0.3178(3) 0.0606(11) Uiso 1.000000 R
H21a H 0.646(2) 0.5659(10) 0.0692(9) 0.0988(17) Uiso 1.000000 GR
H21b H 0.7906(6) 0.5390(15) 0.0948(5) 0.0988(17) Uiso 1.000000 GR
H21c H 0.674(3) 0.4807(5) 0.0469(5) 0.0988(17) Uiso 1.000000 GR
H5a H 0.7262(15) 0.8665(7) 0.5186(12) 0.1030(18) Uiso 1.000000 GR
H5b H 0.673(2) 0.7921(6) 0.4450(4) 0.1030(18) Uiso 1.000000 GR
H5c H 0.5923(10) 0.8311(13) 0.5107(14) 0.1030(18) Uiso 1.000000 GR
H19a H 0.8989(9) 0.4476(5) 0.256(2) 0.1002(18) Uiso 1.000000 GR
H19b H 0.826(2) 0.4206(9) 0.3358(9) 0.1002(18) Uiso 1.000000 GR
H19c H 0.7763(12) 0.3936(5) 0.2047(14) 0.1002(18) Uiso 1.000000 GR
H20a H 0.6029(5) 0.4672(16) 0.2988(8) 0.115(2) Uiso 1.000000 GR
H20b H 0.5368(10) 0.5291(5) 0.202(3) 0.115(2) Uiso 1.000000 GR
H20c H 0.5521(13) 0.4450(12) 0.1656(19) 0.115(2) Uiso 1.000000 GR
H1a H 0.624(2) 0.6157(15) 0.7921(8) 0.142(2) Uiso 1.000000 GR
H1b H 0.7497(7) 0.6189(15) 0.9089(19) 0.142(2) Uiso 1.000000 GR
H1c H 0.647(3) 0.6855(3) 0.877(3) 0.142(2) Uiso 1.000000 GR
H1 H 0.9271(3) 0.75581(16) 0.7232(2) 0.0558(9) Uiso 1.000000 R


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 C9 1.900(4) . ?
S2 O3 1.427(2) . ?
S2 O2 1.426(3) . ?
S2 N1 1.644(3) . ?
S2 C12 1.748(3) . ?
S1 C3 1.766(4) . ?
S1 C6 1.778(4) . ?
O1 C2 1.228(5) . ?
N1 C4 1.375(4) . ?
N1 H1 0.8700 . ?
C15 C18 1.538(5) . ?
C15 C14 1.375(4) . ?
C15 C16 1.396(4) . ?
C12 C13 1.377(4) . ?
C12 C17 1.386(5) . ?
C4 C3 1.369(5) . ?
C4 C5 1.490(5) . ?
C18 C21 1.517(5) . ?
C18 C19 1.536(5) . ?
C18 C20 1.530(5) . ?
C14 C13 1.375(5) . ?
C14 H14 0.9400 . ?
C13 H13 0.9400 . ?
C3 C2 1.470(6) . ?
C6 C11 1.383(5) . ?
C6 C7 1.365(5) . ?
C10 C11 1.371(5) . ?
C10 C9 1.366(5) . ?
C10 H10 0.9400 . ?
C11 H11 0.9400 . ?
C17 C16 1.371(5) . ?
C17 H17 0.9400 . ?
C16 H16 0.9400 . ?
C9 C8 1.370(5) . ?
C2 C1 1.501(5) . ?
C7 C8 1.376(5) . ?
C7 H7 0.9400 . ?
C21 H21a 0.9700 . ?
C21 H21b 0.9700 . ?
C21 H21c 0.9700 . ?
C8 H8 0.9400 . ?
C5 H5a 0.9700 . ?
C5 H5b 0.9700 . ?
C5 H5c 0.9700 . ?
C19 H19a 0.9700 . ?
C19 H19b 0.9700 . ?
C19 H19c 0.9700 . ?
C20 H20a 0.9700 . ?
C20 H20b 0.9700 . ?
C20 H20c 0.9700 . ?
C1 H1a 0.9700 . ?
C1 H1b 0.9700 . ?
C1 H1c 0.9700 . ?

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
O2 S2 O3 119.58(16) . . ?
N1 S2 O3 110.29(15) . . ?
N1 S2 O2 103.45(16) . . ?
C12 S2 O3 108.95(16) . . ?
C12 S2 O2 108.71(16) . . ?
C12 S2 N1 104.81(15) . . ?
C6 S1 C3 104.17(17) . . ?
C4 N1 S2 127.2(2) . . ?
H1 N1 S2 116.41(10) . . ?
H1 N1 C4 116.41(18) . . ?
C14 C15 C18 122.9(3) . . ?
C16 C15 C18 120.3(3) . . ?
C16 C15 C14 116.8(3) . . ?
C13 C12 S2 120.4(3) . . ?
C17 C12 S2 120.2(3) . . ?
C17 C12 C13 119.3(3) . . ?
C3 C4 N1 118.4(3) . . ?
C5 C4 N1 117.6(3) . . ?
C5 C4 C3 124.0(3) . . ?
C21 C18 C15 112.4(3) . . ?
C19 C18 C15 110.0(3) . . ?
C19 C18 C21 107.9(3) . . ?
C20 C18 C15 108.5(3) . . ?
C20 C18 C21 108.5(3) . . ?
C20 C18 C19 109.5(3) . . ?
C13 C14 C15 122.6(3) . . ?
H14 C14 C15 118.7(2) . . ?
H14 C14 C13 118.72(19) . . ?
C14 C13 C12 119.7(3) . . ?
H13 C13 C12 120.2(2) . . ?
H13 C13 C14 120.16(19) . . ?
C4 C3 S1 119.3(3) . . ?
C2 C3 S1 118.1(3) . . ?
C2 C3 C4 122.6(4) . . ?
C11 C6 S1 116.0(3) . . ?
C7 C6 S1 124.7(3) . . ?
C7 C6 C11 119.2(4) . . ?
C9 C10 C11 119.5(4) . . ?
H10 C10 C11 120.3(2) . . ?
H10 C10 C9 120.3(2) . . ?
C10 C11 C6 120.6(4) . . ?
H11 C11 C6 119.7(2) . . ?
H11 C11 C10 119.7(2) . . ?
C16 C17 C12 120.0(3) . . ?
H17 C17 C12 120.0(2) . . ?
H17 C17 C16 120.0(2) . . ?
C17 C16 C15 121.7(3) . . ?
H16 C16 C15 119.2(2) . . ?
H16 C16 C17 119.2(2) . . ?
C10 C9 Br1 119.8(3) . . ?
C8 C9 Br1 119.6(3) . . ?
C8 C9 C10 120.6(4) . . ?
C3 C2 O1 121.8(3) . . ?
C1 C2 O1 118.4(4) . . ?
C1 C2 C3 119.8(4) . . ?
C8 C7 C6 120.4(4) . . ?
H7 C7 C6 119.8(2) . . ?
H7 C7 C8 119.8(2) . . ?
H21a C21 C18 109.5 . . ?
H21b C21 C18 109.5 . . ?
H21b C21 H21a 109.5 . . ?
H21c C21 C18 109.5 . . ?
H21c C21 H21a 109.5 . . ?
H21c C21 H21b 109.5 . . ?
C7 C8 C9 119.7(4) . . ?
H8 C8 C9 120.2(2) . . ?
H8 C8 C7 120.2(2) . . ?
H5a C5 C4 109.5 . . ?
H5b C5 C4 109.5 . . ?
H5b C5 H5a 109.5 . . ?
H5c C5 C4 109.5 . . ?
H5c C5 H5a 109.5 . . ?
H5c C5 H5b 109.5 . . ?
H19a C19 C18 109.5 . . ?
H19b C19 C18 109.5 . . ?
H19b C19 H19a 109.5 . . ?
H19c C19 C18 109.5 . . ?
H19c C19 H19a 109.5 . . ?
H19c C19 H19b 109.5 . . ?
H20a C20 C18 109.5 . . ?
H20b C20 C18 109.5 . . ?
H20b C20 H20a 109.5 . . ?
H20c C20 C18 109.5 . . ?
H20c C20 H20a 109.5 . . ?
H20c C20 H20b 109.5 . . ?
H1a C1 C2 109.5 . . ?
H1b C1 C2 109.5 . . ?
H1b C1 H1a 109.5 . . ?
H1c C1 C2 109.5 . . ?
H1c C1 H1a 109.5 . . ?
H1c C1 H1b 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 C9 C10 C11 -179.9(3) . . . . ?
Br1 C9 C8 C7 179.3(3) . . . . ?
S2 N1 C4 C3 150.3(3) . . . . ?
S2 N1 C4 C5 -29.5(3) . . . . ?
S2 C12 C13 C14 175.4(3) . . . . ?
S2 C12 C17 C16 -176.4(3) . . . . ?
S1 C3 C4 N1 174.7(2) . . . . ?
S1 C3 C4 C5 -5.4(4) . . . . ?
S1 C3 C2 O1 -175.4(3) . . . . ?
S1 C3 C2 C1 6.5(3) . . . . ?
S1 C6 C11 C10 176.6(3) . . . . ?
S1 C6 C7 C8 -177.0(4) . . . . ?
O1 C2 C3 C4 4.2(4) . . . . ?
N1 C4 C3 C2 -4.8(4) . . . . ?
C15 C14 C13 C12 1.2(4) . . . . ?
C15 C16 C17 C12 0.7(4) . . . . ?
C4 C3 C2 C1 -174.0(4) . . . . ?
C6 C11 C10 C9 0.8(4) . . . . ?
C6 C7 C8 C9 0.4(5) . . . . ?
C10 C9 C8 C7 -0.6(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_g250429g_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2n57fj
_database_code_depnum_ccdc_archive 'CCDC 2447897'
loop_
_audit_author_name
_audit_author_address
'Weijian Ye'
;Soochow University
China
;
_audit_update_record             
;
2025-04-30 deposited with the CCDC.	2025-08-15 downloaded from the CCDC.
;
_audit_creation_date             2025-04-30
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2025.03.04 svn.red2d20d0 for OlexSys, GUI svn.r7188)
;
_chemical_formula_moiety         'C18 H18 Br N O3 S2'
_chemical_formula_sum            'C18 H18 Br N O3 S2'
_chemical_formula_weight         440.35
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
Br -0.38188 2.46625 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95570 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
C 0.00313 0.00162 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.01085 0.00610 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
S 0.12485 0.12449 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.86690 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   12.2624(16)
_cell_length_b                   10.7737(17)
_cell_length_c                   14.804(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.006(16)
_cell_angle_gamma                90
_cell_volume                     1941.2(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2709
_cell_measurement_temperature    223.00(10)
_cell_measurement_theta_max      24.7340
_cell_measurement_theta_min      2.2540
_exptl_absorpt_coefficient_mu    2.349
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.81a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_F_000             896.0
_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_unetI/netI     0.0759
_diffrn_reflns_Laue_measured_fraction_full 0.9997
_diffrn_reflns_Laue_measured_fraction_max 0.8691
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11052
_diffrn_reflns_point_group_measured_fraction_full 0.9997
_diffrn_reflns_point_group_measured_fraction_max 0.8691
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         30.48
_diffrn_reflns_theta_min         2.30
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      223.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4471
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9997
_diffrn_measured_fraction_theta_max 0.8691
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -88.00 -57.00   1.00   27.00    --  -13.65 178.00-180.00   31
  2  ω    -81.00 -14.00   1.00   27.00    --  -13.65   0.00   0.00   67
  3  ω      6.00  69.00   1.00   27.00    --  -13.65   0.00   0.00   63
  4  ω    -20.00  21.00   1.00   27.00    --  -13.65  37.00-120.00   41
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0447787000
_diffrn_orient_matrix_UB_12      0.0319930000
_diffrn_orient_matrix_UB_13      0.0244688000
_diffrn_orient_matrix_UB_21      -0.0018991000
_diffrn_orient_matrix_UB_22      0.0447017000
_diffrn_orient_matrix_UB_23      -0.0353458000
_diffrn_orient_matrix_UB_31      -0.0372907000
_diffrn_orient_matrix_UB_32      0.0362554000
_diffrn_orient_matrix_UB_33      0.0218932000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -17
_reflns_limit_k_max              15
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              -11
_reflns_number_gt                2367
_reflns_number_total             5911
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.81a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-alpha (Bourhis et al., 2015)'
_refine_diff_density_max         0.7576
_refine_diff_density_min         -1.3492
_refine_diff_density_rms         0.1543
_refine_ls_d_res_high            0.7007
_refine_ls_d_res_low             8.8573
_refine_ls_goodness_of_fit_ref   0.9194
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    30
_refine_ls_number_parameters     229
_refine_ls_number_reflns         5137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1342
_refine_ls_R_factor_gt           0.0583
_refine_ls_restrained_S_all      0.9194
_refine_ls_shift/su_max          -0.0007
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1445
_refine_ls_wR_factor_ref         0.2056
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C6(H6), C7(H7), C18(H18), C3(H3), C16(H16), C17(H17), C15(H15)
2.b Idealised Me refined as rotating group:
 C9(H9a,H9b,H9c), C12(H12a,H12b,H12c), C1(H1a,H1b,H1c)
;
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
Br1 Br 0.84806(5) 1.07452(6) 0.55629(5) 0.1082(3) Uani 1.000000 .
S1 S 0.23572(8) 0.86640(10) 0.71764(8) 0.0555(3) Uani 1.000000 .
S2 S 0.61994(9) 0.94688(11) 0.57668(8) 0.0585(3) Uani 1.000000 .
O1 O 0.1896(2) 0.9840(3) 0.6913(2) 0.0624(8) Uani 1.000000 .
O3 O 0.4301(2) 0.6554(3) 0.5881(3) 0.0761(10) Uani 1.000000 .
O2 O 0.1698(2) 0.7575(3) 0.7033(2) 0.0699(9) Uani 1.000000 .
C5 C 0.2927(3) 0.8735(3) 0.8318(3) 0.0509(10) Uani 1.000000 .
C13 C 0.7277(3) 0.9230(4) 0.6663(3) 0.0523(10) Uani 1.000000 .
C8 C 0.4283(3) 0.9088(4) 0.6461(3) 0.0472(9) Uani 1.000000 .
C10 C 0.5110(3) 0.8530(4) 0.6051(3) 0.0500(9) Uani 1.000000 .
C11 C 0.5082(3) 0.7231(4) 0.5776(3) 0.0566(10) Uani 1.000000 .
N1 N 0.3396(3) 0.8361(3) 0.6601(2) 0.0582(9) Uani 1.000000 .
H1 H 0.3381(3) 0.7632(3) 0.6347(2) 0.0699(11) Uiso 1.000000 R
C2 C 0.3779(3) 0.8862(5) 1.0144(3) 0.0651(12) Uani 1.000000 .
C4 C 0.3445(4) 0.7708(4) 0.8736(4) 0.0684(13) Uani 1.000000 .
H4 H 0.3507(4) 0.6966(4) 0.8413(4) 0.0821(15) Uiso 1.000000 R
C6 C 0.2833(4) 0.9808(4) 0.8800(3) 0.0624(12) Uani 1.000000 .
H6 H 0.2476(4) 1.0500(4) 0.8514(3) 0.0749(14) Uiso 1.000000 R
C7 C 0.3266(4) 0.9873(4) 0.9710(3) 0.0663(12) Uani 1.000000 .
H7 H 0.3208(4) 1.0616(4) 1.0034(3) 0.0795(14) Uiso 1.000000 R
C9 C 0.4265(4) 1.0412(4) 0.6742(3) 0.0602(11) Uani 1.000000 .
H9a H 0.4983(8) 1.0778(8) 0.6713(19) 0.0903(17) Uiso 1.000000 GR
H9b H 0.3719(17) 1.0856(7) 0.6337(13) 0.0903(17) Uiso 1.000000 GR
H9c H 0.408(2) 1.0464(4) 0.7360(8) 0.0903(17) Uiso 1.000000 GR
C18 C 0.7171(4) 0.8509(5) 0.7429(3) 0.0683(12) Uani 1.000000 .
H18 H 0.6497(4) 0.8126(5) 0.7495(3) 0.0819(15) Uiso 1.000000 R
C12 C 0.6038(4) 0.6679(5) 0.5372(4) 0.0765(14) Uani 1.000000 .
H12a H 0.6693(7) 0.673(3) 0.5809(10) 0.115(2) Uiso 1.000000 GR
H12b H 0.5885(13) 0.5815(10) 0.522(2) 0.115(2) Uiso 1.000000 GR
H12c H 0.6153(18) 0.713(2) 0.4825(14) 0.115(2) Uiso 1.000000 GR
C3 C 0.3870(4) 0.7805(5) 0.9647(4) 0.0778(14) Uani 1.000000 .
H3 H 0.4235(4) 0.7116(5) 0.9933(4) 0.0933(17) Uiso 1.000000 R
C1 C 0.4214(4) 0.8913(6) 1.1137(4) 0.0937(18) Uani 1.000000 .
H1a H 0.427(3) 0.9772(7) 1.1335(8) 0.141(3) Uiso 1.000000 GR
H1b H 0.3720(19) 0.847(3) 1.1486(5) 0.141(3) Uiso 1.000000 GR
H1c H 0.4936(16) 0.853(4) 1.1231(6) 0.141(3) Uiso 1.000000 GR
C16 C 0.9032(5) 0.8924(7) 0.8004(5) 0.106(2) Uani 1.000000 .
H16 H 0.9629(5) 0.8820(7) 0.8459(5) 0.127(2) Uiso 1.000000 R
C17 C 0.8054(5) 0.8359(6) 0.8091(4) 0.0905(17) Uani 1.000000 .
H17 H 0.7982(5) 0.7866(6) 0.8604(4) 0.109(2) Uiso 1.000000 R
C14 C 0.8289(3) 0.9783(4) 0.6601(3) 0.0663(12) Uani 1.000000 .
C15 C 0.9148(4) 0.9638(6) 0.7260(5) 0.0953(18) Uani 1.000000 .
H15 H 0.9822(4) 1.0028(6) 0.7205(5) 0.114(2) Uiso 1.000000 R


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 1.892(5) . ?
S1 O1 1.423(3) . ?
S1 O2 1.425(3) . ?
S1 C5 1.750(5) . ?
S1 N1 1.650(3) . ?
S2 C13 1.773(4) . ?
S2 C10 1.767(4) . ?
O3 C11 1.228(5) . ?
C5 C4 1.383(6) . ?
C5 C6 1.370(6) . ?
C13 C18 1.394(6) . ?
C13 C14 1.390(6) . ?
C8 C10 1.381(5) . ?
C8 N1 1.376(5) . ?
C8 C9 1.486(5) . ?
C10 C11 1.457(6) . ?
C11 C12 1.502(6) . ?
N1 H1 0.8700 . ?
C2 C7 1.377(7) . ?
C2 C3 1.368(7) . ?
C2 C1 1.502(7) . ?
C4 H4 0.9400 . ?
C4 C3 1.388(7) . ?
C6 H6 0.9400 . ?
C6 C7 1.389(6) . ?
C7 H7 0.9400 . ?
C9 H9a 0.9700 . ?
C9 H9b 0.9700 . ?
C9 H9c 0.9700 . ?
C18 H18 0.9400 . ?
C18 C17 1.378(7) . ?
C12 H12a 0.9700 . ?
C12 H12b 0.9700 . ?
C12 H12c 0.9700 . ?
C3 H3 0.9400 . ?
C1 H1a 0.9700 . ?
C1 H1b 0.9700 . ?
C1 H1c 0.9700 . ?
C16 H16 0.9400 . ?
C16 C17 1.365(9) . ?
C16 C15 1.365(9) . ?
C17 H17 0.9400 . ?
C14 C15 1.355(7) . ?
C15 H15 0.9400 . ?

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
O2 S1 O1 119.51(18) . . ?
C5 S1 O1 108.93(19) . . ?
C5 S1 O2 109.38(19) . . ?
N1 S1 O1 109.93(18) . . ?
N1 S1 O2 102.70(17) . . ?
N1 S1 C5 105.40(18) . . ?
C10 S2 C13 104.76(19) . . ?
C4 C5 S1 120.3(3) . . ?
C6 C5 S1 119.4(3) . . ?
C6 C5 C4 120.3(4) . . ?
C18 C13 S2 123.7(3) . . ?
C14 C13 S2 118.6(4) . . ?
C14 C13 C18 117.7(4) . . ?
N1 C8 C10 117.0(3) . . ?
C9 C8 C10 125.2(4) . . ?
C9 C8 N1 117.7(3) . . ?
C8 C10 S2 118.2(3) . . ?
C11 C10 S2 118.4(3) . . ?
C11 C10 C8 123.2(3) . . ?
C10 C11 O3 121.8(3) . . ?
C12 C11 O3 118.3(4) . . ?
C12 C11 C10 119.9(4) . . ?
C8 N1 S1 129.7(3) . . ?
H1 N1 S1 115.13(12) . . ?
H1 N1 C8 115.1(2) . . ?
C3 C2 C7 118.1(5) . . ?
C1 C2 C7 120.9(5) . . ?
C1 C2 C3 121.0(5) . . ?
H4 C4 C5 120.9(3) . . ?
C3 C4 C5 118.2(4) . . ?
C3 C4 H4 120.9(3) . . ?
H6 C6 C5 119.9(3) . . ?
C7 C6 C5 120.1(4) . . ?
C7 C6 H6 119.9(3) . . ?
C6 C7 C2 120.7(5) . . ?
H7 C7 C2 119.6(3) . . ?
H7 C7 C6 119.6(3) . . ?
H9a C9 C8 109.5 . . ?
H9b C9 C8 109.5 . . ?
H9b C9 H9a 109.5 . . ?
H9c C9 C8 109.5 . . ?
H9c C9 H9a 109.5 . . ?
H9c C9 H9b 109.5 . . ?
H18 C18 C13 120.0(2) . . ?
C17 C18 C13 120.1(5) . . ?
C17 C18 H18 120.0(3) . . ?
H12a C12 C11 109.5 . . ?
H12b C12 C11 109.5 . . ?
H12b C12 H12a 109.5 . . ?
H12c C12 C11 109.5 . . ?
H12c C12 H12a 109.5 . . ?
H12c C12 H12b 109.5 . . ?
C4 C3 C2 122.6(4) . . ?
H3 C3 C2 118.7(3) . . ?
H3 C3 C4 118.7(3) . . ?
H1a C1 C2 109.5 . . ?
H1b C1 C2 109.5 . . ?
H1b C1 H1a 109.5 . . ?
H1c C1 C2 109.5 . . ?
H1c C1 H1a 109.5 . . ?
H1c C1 H1b 109.5 . . ?
C17 C16 H16 119.8(4) . . ?
C15 C16 H16 119.8(3) . . ?
C15 C16 C17 120.5(6) . . ?
C16 C17 C18 120.2(6) . . ?
H17 C17 C18 119.9(3) . . ?
H17 C17 C16 119.9(4) . . ?
C13 C14 Br1 119.2(4) . . ?
C15 C14 Br1 119.0(4) . . ?
C15 C14 C13 121.7(5) . . ?
C14 C15 C16 119.8(5) . . ?
H15 C15 C16 120.1(3) . . ?
H15 C15 C14 120.1(4) . . ?

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 C13 S2 -0.8(4) . . . . ?
Br1 C14 C13 C18 178.9(3) . . . . ?
Br1 C14 C15 C16 -178.5(5) . . . . ?
S1 C5 C4 C3 -179.1(4) . . . . ?
S1 C5 C6 C7 179.0(3) . . . . ?
S1 N1 C8 C10 171.4(4) . . . . ?
S1 N1 C8 C9 -10.0(4) . . . . ?
S2 C13 C18 C17 179.3(4) . . . . ?
S2 C13 C14 C15 -179.9(4) . . . . ?
S2 C10 C8 N1 174.3(3) . . . . ?
S2 C10 C8 C9 -4.3(4) . . . . ?
S2 C10 C11 O3 -173.6(3) . . . . ?
S2 C10 C11 C12 7.9(4) . . . . ?
O1 S1 C5 C4 -179.0(3) . . . . ?
O1 S1 C5 C6 2.4(2) . . . . ?
O1 S1 N1 C8 49.4(3) . . . . ?
O3 C11 C10 C8 1.2(5) . . . . ?
O2 S1 C5 C4 48.7(3) . . . . ?
O2 S1 C5 C6 -129.9(3) . . . . ?
O2 S1 N1 C8 177.6(3) . . . . ?
C5 S1 N1 C8 -67.9(3) . . . . ?
C5 C4 C3 C2 1.1(5) . . . . ?
C5 C6 C7 C2 -0.9(5) . . . . ?
C13 S2 C10 C8 99.1(3) . . . . ?
C13 S2 C10 C11 -85.8(3) . . . . ?
C13 C18 C17 C16 0.7(6) . . . . ?
C13 C14 C15 C16 0.6(6) . . . . ?
C8 C10 C11 C12 -177.3(4) . . . . ?
C10 S2 C13 C18 -4.2(3) . . . . ?
C10 S2 C13 C14 175.5(3) . . . . ?
C11 C10 C8 N1 -0.5(5) . . . . ?
C11 C10 C8 C9 -179.1(4) . . . . ?
N1 S1 C5 C4 -61.1(3) . . . . ?
N1 S1 C5 C6 120.3(3) . . . . ?
C4 C5 C6 C7 0.5(5) . . . . ?
C4 C3 C2 C7 -1.5(6) . . . . ?
C4 C3 C2 C1 177.7(5) . . . . ?
C6 C5 C4 C3 -0.6(4) . . . . ?
C6 C7 C2 C3 1.4(5) . . . . ?
C6 C7 C2 C1 -177.8(4) . . . . ?
C18 C13 C14 C15 -0.2(5) . . . . ?
C18 C17 C16 C15 -0.3(7) . . . . ?
C17 C18 C13 C14 -0.4(6) . . . . ?
C17 C16 C15 C14 -0.3(8) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.249
_oxdiff_exptl_absorpt_empirical_full_min 0.819
