# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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. 
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data_1
_database_code_depnum_ccdc_archive 'CCDC 2224310'
loop_
_audit_author_name
_audit_author_address
'Menghua Li'
;Hunan University
China
;
_audit_update_record             
;
2022-12-05 deposited with the CCDC.	2023-05-17 downloaded from the CCDC.
;
_audit_creation_date             2022-12-05
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
2-(4-(tert-butyldisulfaneyl)-1-((3,5-difluorophenyl)sulfonyl)-4-methylpentan-2-yl)benzo[d]thiazole
_chemical_formula_moiety         'C23 H27 F2 N O2 S4'
_chemical_formula_sum            'C23 H27 F2 N O2 S4'
_chemical_formula_weight         516.70
_chemical_melting_point          316
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.0073(2)
_cell_length_b                   11.3650(5)
_cell_length_c                   18.1482(7)
_cell_angle_alpha                99.5990(10)
_cell_angle_beta                 90.8580(10)
_cell_angle_gamma                94.4910(10)
_cell_volume                     1217.44(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9666
_cell_measurement_temperature    150
_cell_measurement_theta_max      28.389
_cell_measurement_theta_min      2.277
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.427
_exptl_absorpt_correction_T_max  0.0962
_exptl_absorpt_correction_T_min  0.0602
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1746 before and 0.0700 after correction.
The Ratio of minimum to maximum transmission is 0.6258.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             542
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.03
_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  0.0446
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14324
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.307
_diffrn_ambient_temperature      150.15
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3738
_reflns_number_total             4211
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.779
_refine_diff_density_min         -0.631
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         4211
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0522
_refine_ls_restrained_S_all      1.138
_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)+(0.0919P)²+1.3767P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1520
_refine_ls_wR_factor_ref         0.1577
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C16, C15, C14, C17
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C15 \\sim C16 \\sim C14 \\sim C17: within 2A with sigma of 0.005 and sigma for
terminal atoms of 0.01 within 2A
Uanis(C14) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C15) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C17)
\\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
4.a Ternary CH refined with riding coordinates:
 C8(H8)
4.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C21(H21A,H21B)
4.c Aromatic/amide H refined with riding coordinates:
 N009(H009), C3(H3), C5(H5), C1(H1), C11(H11), C00Q(H00Q), C12(H12), C13(H13)
4.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C17(H17A,H17B,H17C), C16(H16A,H16B,
 H16C), C14(H14A,H14B,H14C)
;
_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
S001 S 0.05154(11) 0.33863(6) 0.53374(4) 0.0227(2) Uani 1 1 d . . . . .
S002 S 0.35501(13) 0.69899(8) 0.80445(5) 0.0380(2) Uani 1 1 d . . . . .
S003 S -0.02003(13) 0.41464(7) 0.75926(4) 0.0328(2) Uani 1 1 d . . . . .
S004 S 0.51094(19) 0.59729(10) 0.86868(5) 0.0588(3) Uani 1 1 d . . . . .
F005 F 0.3591(3) -0.05673(15) 0.55546(10) 0.0356(4) Uani 1 1 d . . . . .
F006 F -0.3046(3) 0.02858(16) 0.67757(10) 0.0380(5) Uani 1 1 d . . . . .
O007 O -0.1467(3) 0.39660(18) 0.55636(12) 0.0306(5) Uani 1 1 d . . . . .
O008 O 0.0939(4) 0.30979(18) 0.45535(11) 0.0315(5) Uani 1 1 d . . . . .
N009 N 0.3449(4) 0.3123(2) 0.71749(13) 0.0280(6) Uani 1 1 d . . . . .
C00N C 0.0286(5) 0.2857(3) 0.79201(16) 0.0282(6) Uani 1 1 d . . . . .
C00Q C -0.1053(6) 0.2219(3) 0.83740(19) 0.0396(8) Uani 1 1 d . . . . .
C1 C 0.0285(5) -0.0164(3) 0.61781(16) 0.0278(6) Uani 1 1 d . . . . .
C2 C 0.1990(5) 0.0195(3) 0.57524(16) 0.0269(6) Uani 1 1 d . . . . .
C3 C 0.2132(5) 0.1274(2) 0.54992(15) 0.0251(6) Uani 1 1 d . . . . .
C4 C 0.0439(5) 0.2025(2) 0.56957(15) 0.0214(6) Uani 1 1 d . . . . .
C5 C -0.1329(5) 0.1717(2) 0.61295(15) 0.0241(6) Uani 1 1 d . . . . .
C6 C -0.1346(5) 0.0620(3) 0.63551(16) 0.0267(6) Uani 1 1 d . . . . .
C7 C 0.2931(5) 0.4271(2) 0.57545(15) 0.0243(6) Uani 1 1 d . . . . .
C8 C 0.2832(5) 0.4904(2) 0.65689(16) 0.0246(6) Uani 1 1 d . . . . .
C9 C 0.2239(5) 0.4023(2) 0.70899(15) 0.0229(6) Uani 1 1 d . . . . .
C10 C 0.2302(5) 0.2431(3) 0.76487(16) 0.0274(6) Uani 1 1 d . . . . .
C11 C 0.2998(6) 0.1377(3) 0.78352(18) 0.0352(7) Uani 1 1 d . . . . .
C12 C 0.1664(7) 0.0753(3) 0.82713(19) 0.0432(8) Uani 1 1 d . . . . .
C13 C -0.0314(7) 0.1169(3) 0.85390(19) 0.0454(9) Uani 1 1 d . . . . .
C14 C 0.4755(10) 0.7568(7) 0.9963(3) 0.123(2) Uani 1 1 d . U . . .
C15 C 0.6493(8) 0.7037(5) 0.9485(2) 0.0701(12) Uani 1 1 d . U . . .
C16 C 0.7805(12) 0.6191(6) 0.9876(3) 0.117(2) Uani 1 1 d . U . . .
C17 C 0.8125(7) 0.7950(4) 0.9249(2) 0.0581(11) Uani 1 1 d . U . . .
C18 C 0.7593(5) 0.7389(3) 0.73353(17) 0.0297(7) Uani 1 1 d . . . . .
C19 C 0.5156(5) 0.6892(2) 0.71818(16) 0.0236(6) Uani 1 1 d . . . . .
C20 C 0.3963(6) 0.7665(3) 0.6712(2) 0.0412(8) Uani 1 1 d . . . . .
C21 C 0.5143(5) 0.5606(3) 0.67787(17) 0.0283(6) Uani 1 1 d . . . . .
H00Q H -0.241747 0.249992 0.856068 0.048 Uiso 1 1 calc R U . . .
H1 H 0.022749 -0.091603 0.634352 0.033 Uiso 1 1 calc R U . . .
H3 H 0.333374 0.149552 0.520287 0.030 Uiso 1 1 calc R U . . .
H5 H -0.247089 0.223850 0.626388 0.029 Uiso 1 1 calc R U . . .
H7A H 0.418085 0.374821 0.572422 0.029 Uiso 1 1 calc R U . . .
H7B H 0.331685 0.489178 0.544379 0.029 Uiso 1 1 calc R U . . .
H8 H 0.166404 0.548902 0.660006 0.030 Uiso 1 1 calc R U . . .
H11 H 0.437545 0.109277 0.766367 0.042 Uiso 1 1 calc R U . . .
H12 H 0.211291 0.002237 0.839030 0.052 Uiso 1 1 calc R U . . .
H13 H -0.119039 0.072224 0.884431 0.054 Uiso 1 1 calc R U . . .
H14A H 0.421220 0.823980 0.975687 0.185 Uiso 1 1 calc R U . . .
H14B H 0.538054 0.785520 1.046857 0.185 Uiso 1 1 calc R U . . .
H14C H 0.351279 0.696196 0.998245 0.185 Uiso 1 1 calc R U . . .
H16A H 0.679836 0.551034 0.996425 0.176 Uiso 1 1 calc R U . . .
H16B H 0.843413 0.662612 1.035527 0.176 Uiso 1 1 calc R U . . .
H16C H 0.901735 0.589877 0.955804 0.176 Uiso 1 1 calc R U . . .
H17A H 0.935152 0.755022 0.899063 0.087 Uiso 1 1 calc R U . . .
H17B H 0.872123 0.850947 0.969017 0.087 Uiso 1 1 calc R U . . .
H17C H 0.737508 0.839013 0.891009 0.087 Uiso 1 1 calc R U . . .
H18A H 0.764497 0.823483 0.756619 0.045 Uiso 1 1 calc R U . . .
H18B H 0.838522 0.731517 0.686366 0.045 Uiso 1 1 calc R U . . .
H18C H 0.830911 0.693653 0.767419 0.045 Uiso 1 1 calc R U . . .
H20A H 0.240210 0.734649 0.661979 0.062 Uiso 1 1 calc R U . . .
H20B H 0.470476 0.765409 0.623389 0.062 Uiso 1 1 calc R U . . .
H20C H 0.401878 0.848966 0.698157 0.062 Uiso 1 1 calc R U . . .
H21A H 0.597988 0.515501 0.709716 0.034 Uiso 1 1 calc R U . . .
H21B H 0.597798 0.561115 0.631298 0.034 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
S001 O007 1.438(2) . ?
S001 O008 1.437(2) . ?
S001 C4 1.773(3) . ?
S001 C7 1.782(3) . ?
S002 S004 2.0393(14) . ?
S002 C19 1.843(3) . ?
S003 C00N 1.714(3) . ?
S003 C9 1.740(3) . ?
S004 C15 1.864(4) . ?
F005 C2 1.357(3) . ?
F006 C6 1.352(3) . ?
N009 C9 1.328(4) . ?
N009 C10 1.411(4) . ?
C00N C00Q 1.407(5) . ?
C00Q C13 1.382(5) . ?
C00Q H00Q 0.9500 . ?
C1 C6 1.382(4) . ?
C1 H1 0.9500 . ?
C2 C1 1.369(4) . ?
C3 C2 1.376(4) . ?
C3 H3 0.9500 . ?
C4 C3 1.391(4) . ?
C4 C5 1.389(4) . ?
C5 C6 1.375(4) . ?
C5 H5 0.9500 . ?
C7 C8 1.536(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C21 1.555(4) . ?
C8 H8 1.0000 . ?
C9 C8 1.514(4) . ?
C10 C00N 1.405(4) . ?
C10 C11 1.390(4) . ?
C11 C12 1.374(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.378(6) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C14 1.469(8) . ?
C15 C16 1.543(8) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C15 1.491(6) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.532(4) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.531(4) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C19 1.521(4) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?

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
O007 S001 C4 108.13(13) . . ?
O007 S001 C7 110.17(13) . . ?
O008 S001 O007 118.77(13) . . ?
O008 S001 C4 106.76(12) . . ?
O008 S001 C7 106.16(13) . . ?
C4 S001 C7 106.14(13) . . ?
C19 S002 S004 104.99(10) . . ?
C00N S003 C9 89.13(14) . . ?
C15 S004 S002 106.27(19) . . ?
C9 N009 C10 108.2(3) . . ?
C00Q C00N S003 129.0(3) . . ?
C10 C00N S003 110.4(2) . . ?
C10 C00N C00Q 120.5(3) . . ?
C00N C00Q H00Q 121.1 . . ?
C13 C00Q C00N 117.7(3) . . ?
C13 C00Q H00Q 121.1 . . ?
C2 C1 C6 116.7(3) . . ?
C2 C1 H1 121.6 . . ?
C6 C1 H1 121.6 . . ?
F005 C2 C1 118.2(3) . . ?
F005 C2 C3 118.4(3) . . ?
C1 C2 C3 123.5(3) . . ?
C2 C3 C4 117.1(3) . . ?
C2 C3 H3 121.4 . . ?
C4 C3 H3 121.4 . . ?
C3 C4 S001 117.9(2) . . ?
C5 C4 S001 119.8(2) . . ?
C5 C4 C3 122.2(3) . . ?
C4 C5 H5 121.6 . . ?
C6 C5 C4 116.8(3) . . ?
C6 C5 H5 121.6 . . ?
F006 C6 C1 117.8(3) . . ?
F006 C6 C5 118.5(3) . . ?
C5 C6 C1 123.6(3) . . ?
S001 C7 H7A 107.7 . . ?
S001 C7 H7B 107.7 . . ?
C8 C7 S001 118.6(2) . . ?
C8 C7 H7A 107.7 . . ?
C8 C7 H7B 107.7 . . ?
H7A C7 H7B 107.1 . . ?
C7 C8 C21 107.2(2) . . ?
C7 C8 H8 108.6 . . ?
C9 C8 C7 111.6(2) . . ?
C9 C8 C21 112.0(2) . . ?
C9 C8 H8 108.6 . . ?
C21 C8 H8 108.6 . . ?
N009 C9 S003 117.0(2) . . ?
N009 C9 C8 123.7(2) . . ?
C8 C9 S003 119.3(2) . . ?
C00N C10 N009 115.2(3) . . ?
C11 C10 N009 124.8(3) . . ?
C11 C10 C00N 120.0(3) . . ?
C10 C11 H11 120.5 . . ?
C12 C11 C10 119.0(3) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 C13 121.2(3) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C00Q C13 H13 119.2 . . ?
C12 C13 C00Q 121.6(3) . . ?
C12 C13 H13 119.2 . . ?
C15 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
C15 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C14 C15 S004 108.5(3) . . ?
C14 C15 C16 111.6(5) . . ?
C14 C15 C17 113.1(5) . . ?
C16 C15 S004 101.5(4) . . ?
C17 C15 S004 113.5(3) . . ?
C17 C15 C16 108.1(4) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
C19 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C18 C19 S002 112.2(2) . . ?
C20 C19 S002 104.0(2) . . ?
C20 C19 C18 109.9(2) . . ?
C21 C19 S002 111.5(2) . . ?
C21 C19 C18 108.0(2) . . ?
C21 C19 C20 111.3(2) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C8 C21 H21A 107.9 . . ?
C8 C21 H21B 107.9 . . ?
C19 C21 C8 117.5(2) . . ?
C19 C21 H21A 107.9 . . ?
C19 C21 H21B 107.9 . . ?
H21A C21 H21B 107.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S001 C4 C3 C2 -177.0(2) . . . . ?
S001 C4 C5 C6 176.6(2) . . . . ?
S001 C7 C8 C9 57.3(3) . . . . ?
S001 C7 C8 C21 -179.68(19) . . . . ?
S002 S004 C15 C14 68.2(5) . . . . ?
S002 S004 C15 C16 -174.2(3) . . . . ?
S002 S004 C15 C17 -58.4(4) . . . . ?
S003 C00N C00Q C13 177.6(2) . . . . ?
S003 C9 C8 C7 -118.3(2) . . . . ?
S003 C9 C8 C21 121.5(2) . . . . ?
S004 S002 C19 C18 -61.0(2) . . . . ?
S004 S002 C19 C20 -179.73(17) . . . . ?
S004 S002 C19 C21 60.3(2) . . . . ?
F005 C2 C1 C6 -178.5(2) . . . . ?
O007 S001 C4 C3 175.6(2) . . . . ?
O007 S001 C4 C5 -1.6(3) . . . . ?
O007 S001 C7 C8 39.7(2) . . . . ?
O008 S001 C4 C3 46.7(2) . . . . ?
O008 S001 C4 C5 -130.4(2) . . . . ?
O008 S001 C7 C8 169.6(2) . . . . ?
N009 C9 C8 C7 59.7(3) . . . . ?
N009 C9 C8 C21 -60.5(3) . . . . ?
N009 C10 C00N S003 -0.6(3) . . . . ?
N009 C10 C00N C00Q 177.5(3) . . . . ?
N009 C10 C11 C12 -176.5(3) . . . . ?
C00N S003 C9 N009 -3.1(2) . . . . ?
C00N S003 C9 C8 175.1(2) . . . . ?
C00N C00Q C13 C12 0.0(5) . . . . ?
C00N C10 C11 C12 1.5(4) . . . . ?
C2 C1 C6 F006 -179.9(2) . . . . ?
C2 C1 C6 C5 -0.1(4) . . . . ?
C3 C2 C1 C6 -0.3(4) . . . . ?
C3 C4 C5 C6 -0.5(4) . . . . ?
C4 S001 C7 C8 -77.1(2) . . . . ?
C4 C3 C2 F005 178.5(2) . . . . ?
C4 C3 C2 C1 0.3(4) . . . . ?
C4 C5 C6 F006 -179.7(2) . . . . ?
C4 C5 C6 C1 0.5(4) . . . . ?
C5 C4 C3 C2 0.1(4) . . . . ?
C7 S001 C4 C3 -66.2(2) . . . . ?
C7 S001 C4 C5 116.6(2) . . . . ?
C7 C8 C21 C19 133.8(3) . . . . ?
C8 C21 C19 S002 55.7(3) . . . . ?
C8 C21 C19 C18 179.4(2) . . . . ?
C8 C21 C19 C20 -59.9(3) . . . . ?
C9 S003 C00N C00Q -176.0(3) . . . . ?
C9 S003 C00N C10 1.9(2) . . . . ?
C9 N009 C10 C00N -1.6(3) . . . . ?
C9 N009 C10 C11 176.5(3) . . . . ?
C9 C8 C21 C19 -103.4(3) . . . . ?
C10 N009 C9 S003 3.2(3) . . . . ?
C10 N009 C9 C8 -174.9(2) . . . . ?
C10 C00N C00Q C13 -0.1(5) . . . . ?
C10 C11 C12 C13 -1.5(5) . . . . ?
C11 C10 C00N S003 -178.8(2) . . . . ?
C11 C10 C00N C00Q -0.7(4) . . . . ?
C11 C12 C13 C00Q 0.8(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_2023032402_0m
_database_code_depnum_ccdc_archive 'CCDC 2251587'
loop_
_audit_author_name
_audit_author_address
'Baoxu Wang'
;Hunan University
China
;
_audit_update_record             
;
2023-03-25 deposited with the CCDC.	2023-05-17 downloaded from the CCDC.
;
_audit_creation_date             2023-03-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
2-(5,5-dimethyl-4,5-dihydrothiophen-3-yl)-1-methyl-1H-benzo[d]imidazole
_chemical_formula_moiety         'C14 N2 S'
_chemical_formula_sum            'C14 N2 S'
_chemical_formula_weight         228.22
_chemical_melting_point          388
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'
N N 0.0061 0.0033 '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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   11.807(4)
_cell_length_b                   10.063(3)
_cell_length_c                   21.134(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2511.1(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9944
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.328
_cell_measurement_theta_min      2.834
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5278
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1557 before and 0.0635 after correction.
The Ratio of minimum to maximum transmission is 0.7078.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            44554
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.332
_diffrn_reflns_theta_min         2.829
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2810
_reflns_number_total             3108
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.873
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.115
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         3108
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0662
_refine_ls_restrained_S_all      1.083
_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)+(0.1561P)²+3.2388P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2314
_refine_ls_wR_factor_ref         0.2379
_refine_special_details          ?
_olex2_refinement_description    
;

;
_atom_sites_solution_hydrogens   .
_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
S001 S 0.35517(6) -0.00291(5) 0.70490(3) 0.0264(3) Uani 1 1 d . . . . .
N002 N 0.19282(16) 0.2839(2) 0.54760(9) 0.0205(4) Uani 1 1 d . . . . .
N003 N 0.37379(17) 0.3559(2) 0.54189(9) 0.0220(4) Uani 1 1 d . . . . .
C004 C 0.33482(19) 0.1951(2) 0.62558(10) 0.0200(4) Uani 1 1 d . . . . .
C005 C 0.30095(18) 0.2772(2) 0.57187(11) 0.0195(5) Uani 1 1 d . . . . .
C006 C 0.43447(19) 0.2348(2) 0.66627(11) 0.0224(5) Uani 1 1 d . . . . .
C007 C 0.31048(19) 0.4160(2) 0.49438(11) 0.0213(5) Uani 1 1 d . . . . .
C008 C 0.19719(19) 0.3728(2) 0.49792(11) 0.0216(5) Uani 1 1 d . . . . .
C009 C 0.42985(19) 0.1523(2) 0.72790(11) 0.0217(5) Uani 1 1 d . . . . .
C00A C 0.2917(2) 0.0749(2) 0.64028(11) 0.0237(5) Uani 1 1 d . . . . .
C00B C 0.08849(19) 0.2241(3) 0.57212(12) 0.0260(5) Uani 1 1 d . . . . .
C00C C 0.1130(2) 0.4204(3) 0.45726(11) 0.0271(5) Uani 1 1 d . . . . .
C00D C 0.3436(2) 0.5096(2) 0.44889(13) 0.0262(6) Uani 1 1 d . . . . .
C00E C 0.3595(2) 0.2229(3) 0.77838(13) 0.0303(6) Uani 1 1 d . . . . .
C00F C 0.5479(2) 0.1181(3) 0.75337(13) 0.0308(6) Uani 1 1 d . . . . .
C00G C 0.2598(2) 0.5575(3) 0.40826(12) 0.0308(6) Uani 1 1 d . . . . .
C00H C 0.1465(2) 0.5129(3) 0.41270(14) 0.0306(6) Uani 1 1 d . . . . .


_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
S001 C009 1.858(2) . ?
S001 C00A 1.744(2) . ?
N002 C005 1.378(3) . ?
N002 C008 1.381(3) . ?
N002 C00B 1.465(3) . ?
N003 C005 1.329(3) . ?
N003 C007 1.391(3) . ?
C004 C005 1.460(3) . ?
C004 C006 1.511(3) . ?
C004 C00A 1.349(3) . ?
C006 C009 1.545(3) . ?
C007 C008 1.408(3) . ?
C007 C00D 1.401(3) . ?
C008 C00C 1.399(3) . ?
C009 C00E 1.528(3) . ?
C009 C00F 1.533(3) . ?
C00C C00H 1.382(4) . ?
C00D C00G 1.395(4) . ?
C00G C00H 1.414(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00A S001 C009 91.82(11) . . ?
C005 N002 C008 106.26(18) . . ?
C005 N002 C00B 128.9(2) . . ?
C008 N002 C00B 124.49(19) . . ?
C005 N003 C007 104.80(19) . . ?
C005 C004 C006 120.42(19) . . ?
C00A C004 C005 125.7(2) . . ?
C00A C004 C006 113.6(2) . . ?
N002 C005 C004 124.8(2) . . ?
N003 C005 N002 113.2(2) . . ?
N003 C005 C004 122.0(2) . . ?
C004 C006 C009 108.07(18) . . ?
N003 C007 C008 109.7(2) . . ?
N003 C007 C00D 129.6(2) . . ?
C00D C007 C008 120.6(2) . . ?
N002 C008 C007 106.0(2) . . ?
N002 C008 C00C 131.5(2) . . ?
C00C C008 C007 122.5(2) . . ?
C006 C009 S001 104.35(15) . . ?
C00E C009 S001 108.39(17) . . ?
C00E C009 C006 111.0(2) . . ?
C00E C009 C00F 110.7(2) . . ?
C00F C009 S001 109.53(16) . . ?
C00F C009 C006 112.6(2) . . ?
C004 C00A S001 114.86(18) . . ?
C00H C00C C008 116.5(2) . . ?
C00G C00D C007 117.2(2) . . ?
C00D C00G C00H 121.3(2) . . ?
C00C C00H C00G 122.0(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate and n-hexane'
