# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_ga_90329a_a
_database_code_depnum_ccdc_archive 'CCDC 1965442'
loop_
_audit_author_name
_audit_author_address
'Zhang Jun' University
_audit_update_record             
;
2019-11-13 deposited with the CCDC.	2020-02-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H19 Cl N2 O2 S'
_chemical_formula_weight         410.90

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'
Cl Cl 0.3281 0.5435 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

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                   6.7878(2)
_cell_length_b                   22.1588(9)
_cell_length_c                   13.8692(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.581(2)
_cell_angle_gamma                90
_cell_volume                     2072.31(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1422
_cell_measurement_theta_min      3.29
_cell_measurement_theta_max      31.61

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.801
_shelx_estimated_absorpt_T_min   0.840
_shelx_estimated_absorpt_T_max   0.900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.655
_exptl_absorpt_correction_T_max  0.752
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.34138
_diffrn_radiation_type           GaK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19378
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.455
_diffrn_reflns_theta_max         57.989
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4385
_reflns_number_gt                3806
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0569P)²+0.6365P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4385
_refine_ls_number_parameters     261
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1173
_refine_ls_wR_factor_gt          0.1130
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.35864(6) 0.30779(2) 0.39676(3) 0.04203(13) Uani 1 1 d . . . . .
Cl1 Cl 1.00757(9) 0.10748(3) 0.21968(5) 0.0873(2) Uani 1 1 d . . . . .
N1 N 0.3452(4) 0.26275(10) 0.60983(14) 0.0734(6) Uani 1 1 d . . . . .
H1A H 0.275(5) 0.2944(14) 0.589(2) 0.091(9) Uiso 1 1 d . . . . .
H1B H 0.346(4) 0.2495(11) 0.665(2) 0.067(7) Uiso 1 1 d . . . . .
N2 N 0.6623(4) 0.52677(10) 0.38301(18) 0.0921(7) Uani 1 1 d . . . . .
O1 O 0.2869(2) 0.29034(6) 0.29890(9) 0.0553(3) Uani 1 1 d . . . . .
O2 O 0.2152(2) 0.33353(6) 0.45402(10) 0.0572(3) Uani 1 1 d . . . . .
C1 C 0.4575(3) 0.23371(8) 0.55176(13) 0.0474(4) Uani 1 1 d . . . . .
C2 C 0.4757(2) 0.24680(7) 0.45701(12) 0.0412(3) Uani 1 1 d . . . . .
C3 C 0.5711(3) 0.18089(8) 0.59784(12) 0.0478(4) Uani 1 1 d . . . . .
C4 C 0.4829(3) 0.12310(8) 0.59316(13) 0.0486(4) Uani 1 1 d . . . . .
C5 C 0.2876(3) 0.11277(9) 0.54779(16) 0.0594(5) Uani 1 1 d . . . . .
H5 H 0.212574 0.144544 0.519316 0.071 Uiso 1 1 calc R U . . .
C6 C 0.2110(4) 0.05599(11) 0.5463(2) 0.0854(8) Uani 1 1 d . . . . .
H6 H 0.083484 0.049480 0.515831 0.103 Uiso 1 1 calc R U . . .
C7 C 0.3175(5) 0.00739(12) 0.5889(2) 0.0945(9) Uani 1 1 d . . . . .
H7 H 0.261186 -0.030913 0.587178 0.113 Uiso 1 1 calc R U . . .
C8 C 0.5032(4) 0.01623(11) 0.63284(19) 0.0743(6) Uani 1 1 d . . . . .
H8 H 0.573288 -0.016474 0.661327 0.089 Uiso 1 1 calc R U . . .
C9 C 0.5945(3) 0.07381(9) 0.63687(14) 0.0533(4) Uani 1 1 d . . . . .
C10 C 0.7870(3) 0.08278(11) 0.68175(16) 0.0649(5) Uani 1 1 d . . . . .
H10 H 0.860425 0.050277 0.708819 0.078 Uiso 1 1 calc R U . . .
C11 C 0.8679(3) 0.13960(12) 0.68589(17) 0.0724(6) Uani 1 1 d . . . . .
H11 H 0.995762 0.145726 0.716268 0.087 Uiso 1 1 calc R U . . .
C12 C 0.7573(3) 0.18851(10) 0.64413(15) 0.0579(5) Uani 1 1 d . . . . .
H12 H 0.812513 0.226960 0.648225 0.069 Uiso 1 1 calc R U . . .
C13 C 0.5453(3) 0.36236(8) 0.38574(14) 0.0528(4) Uani 1 1 d . . . . .
H13A H 0.643215 0.345354 0.347812 0.063 Uiso 1 1 calc R U . . .
H13B H 0.486049 0.396910 0.350546 0.063 Uiso 1 1 calc R U . . .
C14 C 0.6485(4) 0.38356(9) 0.48198(16) 0.0624(5) Uani 1 1 d . . . . .
H14A H 0.708492 0.349259 0.517552 0.075 Uiso 1 1 calc R U . . .
H14B H 0.551684 0.401112 0.520033 0.075 Uiso 1 1 calc R U . . .
C15 C 0.8094(4) 0.43056(11) 0.4682(2) 0.0776(7) Uani 1 1 d . . . . .
H15A H 0.878297 0.441128 0.531090 0.093 Uiso 1 1 calc R U . . .
H15B H 0.905366 0.412982 0.429705 0.093 Uiso 1 1 calc R U . . .
C16 C 0.7277(4) 0.48501(10) 0.42052(18) 0.0679(6) Uani 1 1 d . . . . .
C17 C 0.6069(2) 0.21150(7) 0.39824(11) 0.0397(3) Uani 1 1 d . . . . .
C18 C 0.8077(3) 0.22394(9) 0.40302(15) 0.0537(4) Uani 1 1 d . . . . .
H18 H 0.861394 0.254403 0.444075 0.064 Uiso 1 1 calc R U . . .
C19 C 0.9300(3) 0.19227(9) 0.34837(16) 0.0590(5) Uani 1 1 d . . . . .
H19 H 1.064684 0.201065 0.352719 0.071 Uiso 1 1 calc R U . . .
C20 C 0.8503(3) 0.14759(9) 0.28750(14) 0.0513(4) Uani 1 1 d . . . . .
C21 C 0.6520(3) 0.13405(8) 0.27973(15) 0.0534(4) Uani 1 1 d . . . . .
H21 H 0.599454 0.103874 0.237799 0.064 Uiso 1 1 calc R U . . .
C22 C 0.5313(3) 0.16617(8) 0.33554(14) 0.0483(4) Uani 1 1 d . . . . .
H22 H 0.396712 0.157154 0.330862 0.058 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
S1 O1 1.4412(13) . ?
S1 O2 1.4426(13) . ?
S1 C2 1.7331(17) . ?
S1 C13 1.7706(19) . ?
Cl1 C20 1.7450(18) . ?
N1 C1 1.336(2) . ?
N1 H1A 0.88(3) . ?
N1 H1B 0.82(3) . ?
N2 C16 1.127(3) . ?
C1 C2 1.365(2) . ?
C1 C3 1.503(3) . ?
C2 C17 1.496(2) . ?
C3 C12 1.361(3) . ?
C3 C4 1.412(3) . ?
C4 C5 1.420(3) . ?
C4 C9 1.424(3) . ?
C5 C6 1.360(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.390(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.350(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.417(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.396(3) . ?
C10 C11 1.372(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.405(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.510(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.537(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.455(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C17 C18 1.385(2) . ?
C17 C22 1.388(2) . ?
C18 C19 1.378(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.371(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.371(3) . ?
C21 C22 1.387(2) . ?
C21 H21 0.9300 . ?
C22 H22 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 116.61(8) . . ?
O1 S1 C2 109.36(8) . . ?
O2 S1 C2 110.11(8) . . ?
O1 S1 C13 105.65(9) . . ?
O2 S1 C13 108.20(9) . . ?
C2 S1 C13 106.33(9) . . ?
C1 N1 H1A 120.5(19) . . ?
C1 N1 H1B 116.8(17) . . ?
H1A N1 H1B 123(3) . . ?
N1 C1 C2 126.78(18) . . ?
N1 C1 C3 114.77(16) . . ?
C2 C1 C3 118.45(15) . . ?
C1 C2 C17 122.59(15) . . ?
C1 C2 S1 122.89(13) . . ?
C17 C2 S1 114.45(11) . . ?
C12 C3 C4 119.99(18) . . ?
C12 C3 C1 120.49(17) . . ?
C4 C3 C1 119.52(16) . . ?
C3 C4 C5 122.42(17) . . ?
C3 C4 C9 118.31(17) . . ?
C5 C4 C9 119.27(17) . . ?
C6 C5 C4 119.5(2) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C7 122.1(3) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 H6 119.0 . . ?
C8 C7 C6 119.5(2) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C8 C9 122.0(2) . . ?
C7 C8 H8 119.0 . . ?
C9 C8 H8 119.0 . . ?
C10 C9 C8 121.9(2) . . ?
C10 C9 C4 120.36(19) . . ?
C8 C9 C4 117.7(2) . . ?
C11 C10 C9 119.9(2) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 119.9(2) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C3 C12 C11 121.50(19) . . ?
C3 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C14 C13 S1 113.60(14) . . ?
C14 C13 H13A 108.8 . . ?
S1 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
S1 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C13 C14 C15 111.42(19) . . ?
C13 C14 H14A 109.3 . . ?
C15 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
C15 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
C16 C15 C14 112.3(2) . . ?
C16 C15 H15A 109.1 . . ?
C14 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
C14 C15 H15B 109.1 . . ?
H15A C15 H15B 107.9 . . ?
N2 C16 C15 179.1(3) . . ?
C18 C17 C22 117.75(15) . . ?
C18 C17 C2 120.95(15) . . ?
C22 C17 C2 121.28(15) . . ?
C19 C18 C17 121.57(17) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C20 C19 C18 119.08(17) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C21 C20 C19 121.40(16) . . ?
C21 C20 Cl1 120.13(14) . . ?
C19 C20 Cl1 118.47(15) . . ?
C20 C21 C22 118.77(17) . . ?
C20 C21 H21 120.6 . . ?
C22 C21 H21 120.6 . . ?
C21 C22 C17 121.42(16) . . ?
C21 C22 H22 119.3 . . ?
C17 C22 H22 119.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C17 179.7(2) . . . . ?
C3 C1 C2 C17 -1.3(3) . . . . ?
N1 C1 C2 S1 3.0(3) . . . . ?
C3 C1 C2 S1 -177.97(13) . . . . ?
O1 S1 C2 C1 -140.51(15) . . . . ?
O2 S1 C2 C1 -11.14(18) . . . . ?
C13 S1 C2 C1 105.85(16) . . . . ?
O1 S1 C2 C17 42.54(14) . . . . ?
O2 S1 C2 C17 171.91(12) . . . . ?
C13 S1 C2 C17 -71.10(14) . . . . ?
N1 C1 C3 C12 -90.5(2) . . . . ?
C2 C1 C3 C12 90.4(2) . . . . ?
N1 C1 C3 C4 89.3(2) . . . . ?
C2 C1 C3 C4 -89.9(2) . . . . ?
C12 C3 C4 C5 178.52(19) . . . . ?
C1 C3 C4 C5 -1.2(3) . . . . ?
C12 C3 C4 C9 -0.7(3) . . . . ?
C1 C3 C4 C9 179.57(15) . . . . ?
C3 C4 C5 C6 -179.6(2) . . . . ?
C9 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 C7 0.7(4) . . . . ?
C5 C6 C7 C8 -0.4(5) . . . . ?
C6 C7 C8 C9 -0.2(5) . . . . ?
C7 C8 C9 C10 -179.6(3) . . . . ?
C7 C8 C9 C4 0.4(4) . . . . ?
C3 C4 C9 C10 -0.9(3) . . . . ?
C5 C4 C9 C10 179.86(19) . . . . ?
C3 C4 C9 C8 179.12(19) . . . . ?
C5 C4 C9 C8 -0.1(3) . . . . ?
C8 C9 C10 C11 -178.5(2) . . . . ?
C4 C9 C10 C11 1.5(3) . . . . ?
C9 C10 C11 C12 -0.6(3) . . . . ?
C4 C3 C12 C11 1.7(3) . . . . ?
C1 C3 C12 C11 -178.58(19) . . . . ?
C10 C11 C12 C3 -1.0(3) . . . . ?
O1 S1 C13 C14 -176.37(15) . . . . ?
O2 S1 C13 C14 58.05(17) . . . . ?
C2 S1 C13 C14 -60.21(17) . . . . ?
S1 C13 C14 C15 179.73(16) . . . . ?
C13 C14 C15 C16 62.6(3) . . . . ?
C1 C2 C17 C18 -83.4(2) . . . . ?
S1 C2 C17 C18 93.61(18) . . . . ?
C1 C2 C17 C22 98.1(2) . . . . ?
S1 C2 C17 C22 -84.91(18) . . . . ?
C22 C17 C18 C19 -0.6(3) . . . . ?
C2 C17 C18 C19 -179.19(18) . . . . ?
C17 C18 C19 C20 0.3(3) . . . . ?
C18 C19 C20 C21 0.2(3) . . . . ?
C18 C19 C20 Cl1 -179.43(17) . . . . ?
C19 C20 C21 C22 -0.5(3) . . . . ?
Cl1 C20 C21 C22 179.14(15) . . . . ?
C20 C21 C22 C17 0.2(3) . . . . ?
C18 C17 C22 C21 0.3(3) . . . . ?
C2 C17 C22 C21 178.89(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1B O1 0.82(3) 2.13(3) 2.942(2) 168(2) 4_566
N1 H1A O2 0.88(3) 2.06(3) 2.733(3) 133(3) .

_refine_diff_density_max         0.430
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.040

