# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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 
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data_shelxl
_audit_block_doi                 10.5517/ccdc.csd.cc1q8jbv
_database_code_depnum_ccdc_archive 'CCDC 1587117'
loop_
_audit_author_name
_audit_author_address
'minxuan zhang' 'nankai university'
_audit_update_record             
;
2017-11-22 deposited with the CCDC.	2019-04-11 downloaded from the CCDC.
;
_audit_creation_date             2017-11-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/8
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C19 H19 Cl2 N O3 S'
_chemical_formula_sum            'C19 H19 Cl2 N O3 S'
_chemical_formula_weight         412.31
_chemical_absolute_configuration ad
_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'
Cl Cl 0.1484 0.1585 '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      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                   8.4226(17)
_cell_length_b                   14.002(3)
_cell_length_c                   16.760(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1976.6(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5783
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.8505
_cell_measurement_theta_min      1.8943
_shelx_estimated_absorpt_T_max   0.948
_shelx_estimated_absorpt_T_min   0.915
_exptl_absorpt_coefficient_mu    0.452
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8035
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            19834
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.844
_diffrn_reflns_theta_min         2.430
_diffrn_ambient_temperature      113.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku Saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                4042
_reflns_number_total             4700
_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       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 
;
 Flack x determined using 1341 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.09(3)
_refine_ls_extinction_coef       0.0159(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/8 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         4700
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0382
_refine_ls_restrained_S_all      0.993
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0441P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0769
_refine_ls_wR_factor_ref         0.0808
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1
 0.9 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15)
3.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 1.24932(10) 0.68333(6) -0.30351(4) 0.0441(2) Uani 1 1 d . . . . .
Cl2 Cl 0.91362(9) 0.95827(5) -0.15138(5) 0.0389(2) Uani 1 1 d . . . . .
S1 S 0.99321(8) 0.45987(5) -0.01493(4) 0.02960(17) Uani 1 1 d . . . . .
O1 O 0.9129(2) 0.81028(13) -0.01768(12) 0.0294(4) Uani 1 1 d . . . . .
O2 O 1.1285(2) 0.84292(14) 0.09444(14) 0.0369(5) Uani 1 1 d . . . . .
O3 O 1.0365(3) 0.43309(16) -0.09778(15) 0.0546(7) Uani 1 1 d . . . . .
N1 N 0.9089(3) 0.56751(14) -0.01116(14) 0.0239(5) Uani 1 1 d D . . . .
C1 C 0.9904(3) 0.78732(18) -0.08682(16) 0.0259(5) Uani 1 1 d . . . . .
C2 C 1.0028(3) 0.84720(18) -0.15243(18) 0.0290(6) Uani 1 1 d . . . . .
C3 C 1.0832(3) 0.8141(2) -0.21953(18) 0.0324(6) Uani 1 1 d . . . . .
H3 H 1.0945 0.8538 -0.2652 0.039 Uiso 1 1 calc R . . . .
C4 C 1.1468(3) 0.7225(2) -0.21920(18) 0.0313(6) Uani 1 1 d . . . . .
C5 C 1.1314(3) 0.6613(2) -0.15438(17) 0.0289(6) Uani 1 1 d . . . . .
H5 H 1.1731 0.5983 -0.1556 0.035 Uiso 1 1 calc R . . . .
C6 C 1.0527(3) 0.69608(19) -0.08801(16) 0.0255(6) Uani 1 1 d . . . . .
C7 C 1.0170(3) 0.64868(17) -0.00873(16) 0.0243(5) Uani 1 1 d . . . . .
H7 H 1.1187 0.6291 0.0173 0.029 Uiso 1 1 calc R . . . .
C8 C 0.9423(3) 0.73396(18) 0.03838(16) 0.0252(6) Uani 1 1 d . . . . .
H8 H 0.8396 0.7132 0.0628 0.030 Uiso 1 1 calc R . . . .
C9 C 1.0535(3) 0.76990(19) 0.10374(17) 0.0264(6) Uani 1 1 d . . . . .
C10 C 1.0716(3) 0.70919(19) 0.17604(16) 0.0267(6) Uani 1 1 d . . . . .
C11 C 0.9848(4) 0.6248(2) 0.18663(16) 0.0312(6) Uani 1 1 d . . . . .
H11 H 0.9087 0.6061 0.1478 0.037 Uiso 1 1 calc R . . . .
C12 C 1.0095(4) 0.5687(2) 0.25339(18) 0.0372(7) Uani 1 1 d . . . . .
H12 H 0.9504 0.5115 0.2605 0.045 Uiso 1 1 calc R . . . .
C13 C 1.1207(4) 0.5960(2) 0.30978(19) 0.0382(7) Uani 1 1 d . . . . .
H13 H 1.1381 0.5573 0.3555 0.046 Uiso 1 1 calc R . . . .
C14 C 1.2066(4) 0.6794(2) 0.29994(18) 0.0378(7) Uani 1 1 d . . . . .
H14 H 1.2832 0.6975 0.3387 0.045 Uiso 1 1 calc R . . . .
C15 C 1.1816(3) 0.7366(2) 0.23386(17) 0.0312(6) Uani 1 1 d . . . . .
H15 H 1.2392 0.7944 0.2279 0.037 Uiso 1 1 calc R . . . .
C16 C 0.8141(3) 0.38986(18) 0.00938(18) 0.0294(6) Uani 1 1 d . . . . .
C17 C 0.6833(4) 0.4107(2) -0.0501(2) 0.0501(9) Uani 1 1 d . . . . .
H17A H 0.7237 0.4016 -0.1044 0.075 Uiso 1 1 calc GR . . . .
H17B H 0.6474 0.4768 -0.0436 0.075 Uiso 1 1 calc GR . . . .
H17C H 0.5941 0.3671 -0.0408 0.075 Uiso 1 1 calc GR . . . .
C18 C 0.8703(4) 0.28617(18) 0.0028(2) 0.0391(7) Uani 1 1 d . . . . .
H18A H 0.7828 0.2431 0.0168 0.059 Uiso 1 1 calc GR . . . .
H18B H 0.9593 0.2757 0.0394 0.059 Uiso 1 1 calc GR . . . .
H18C H 0.9047 0.2733 -0.0520 0.059 Uiso 1 1 calc GR . . . .
C19 C 0.7680(4) 0.4129(2) 0.09515(19) 0.0422(8) Uani 1 1 d . . . . .
H19A H 0.7282 0.4785 0.0981 0.063 Uiso 1 1 calc GR . . . .
H19B H 0.8613 0.4062 0.1297 0.063 Uiso 1 1 calc GR . . . .
H19C H 0.6850 0.3686 0.1128 0.063 Uiso 1 1 calc GR . . . .
H1 H 0.826(3) 0.577(2) -0.0437(15) 0.030(8) Uiso 1 1 d 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
Cl1 C4 1.744(3) . ?
Cl2 C2 1.727(3) . ?
S1 O3 1.484(2) . ?
S1 N1 1.667(2) . ?
S1 C16 1.845(3) . ?
O1 C1 1.368(3) . ?
O1 C8 1.444(3) . ?
O2 C9 1.212(3) . ?
N1 C7 1.457(3) . ?
N1 H1 0.895(13) . ?
C1 C2 1.387(4) . ?
C1 C6 1.381(4) . ?
C2 C3 1.392(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(4) . ?
C4 C5 1.389(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.383(4) . ?
C6 C7 1.515(4) . ?
C7 H7 1.0000 . ?
C7 C8 1.564(4) . ?
C8 H8 1.0000 . ?
C8 C9 1.527(4) . ?
C9 C10 1.488(4) . ?
C10 C11 1.401(4) . ?
C10 C15 1.394(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.383(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.385(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.384(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.382(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.514(4) . ?
C16 C18 1.531(4) . ?
C16 C19 1.523(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 N1 111.63(13) . . ?
O3 S1 C16 105.87(14) . . ?
N1 S1 C16 97.10(11) . . ?
C1 O1 C8 107.18(19) . . ?
S1 N1 H1 116.0(19) . . ?
C7 N1 S1 116.10(17) . . ?
C7 N1 H1 113.1(19) . . ?
O1 C1 C2 124.4(2) . . ?
O1 C1 C6 114.3(2) . . ?
C6 C1 C2 121.3(3) . . ?
C1 C2 Cl2 120.2(2) . . ?
C1 C2 C3 118.4(2) . . ?
C3 C2 Cl2 121.3(2) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.4(3) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 Cl1 118.5(2) . . ?
C5 C4 Cl1 119.1(2) . . ?
C5 C4 C3 122.4(3) . . ?
C4 C5 H5 121.4 . . ?
C6 C5 C4 117.2(3) . . ?
C6 C5 H5 121.4 . . ?
C1 C6 C5 121.3(3) . . ?
C1 C6 C7 108.5(2) . . ?
C5 C6 C7 130.2(2) . . ?
N1 C7 C6 116.2(2) . . ?
N1 C7 H7 109.5 . . ?
N1 C7 C8 111.0(2) . . ?
C6 C7 H7 109.5 . . ?
C6 C7 C8 100.8(2) . . ?
C8 C7 H7 109.5 . . ?
O1 C8 C7 107.8(2) . . ?
O1 C8 H8 109.4 . . ?
O1 C8 C9 109.1(2) . . ?
C7 C8 H8 109.4 . . ?
C9 C8 C7 111.5(2) . . ?
C9 C8 H8 109.4 . . ?
O2 C9 C8 120.4(3) . . ?
O2 C9 C10 122.2(3) . . ?
C10 C9 C8 117.3(2) . . ?
C11 C10 C9 122.1(2) . . ?
C15 C10 C9 118.5(3) . . ?
C15 C10 C11 119.4(3) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.2(3) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C13 119.7(3) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.4(3) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.3(3) . . ?
C15 C14 H14 119.9 . . ?
C10 C15 H15 120.0 . . ?
C14 C15 C10 120.0(3) . . ?
C14 C15 H15 120.0 . . ?
C17 C16 S1 110.3(2) . . ?
C17 C16 C18 111.1(3) . . ?
C17 C16 C19 113.3(3) . . ?
C18 C16 S1 103.6(2) . . ?
C19 C16 S1 107.7(2) . . ?
C19 C16 C18 110.3(2) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

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 H1 O2 0.895(13) 2.181(17) 3.016(3) 155(3) 4_465

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
Cl1 C4 C5 C6 178.40(19) . . . . ?
Cl2 C2 C3 C4 -176.9(2) . . . . ?
S1 N1 C7 C6 96.0(2) . . . . ?
S1 N1 C7 C8 -149.61(18) . . . . ?
O1 C1 C2 Cl2 -1.5(4) . . . . ?
O1 C1 C2 C3 -179.0(2) . . . . ?
O1 C1 C6 C5 178.5(2) . . . . ?
O1 C1 C6 C7 -1.0(3) . . . . ?
O1 C8 C9 O2 -15.7(3) . . . . ?
O1 C8 C9 C10 167.5(2) . . . . ?
O2 C9 C10 C11 180.0(2) . . . . ?
O2 C9 C10 C15 -1.6(4) . . . . ?
O3 S1 N1 C7 -83.6(2) . . . . ?
O3 S1 C16 C17 -57.6(3) . . . . ?
O3 S1 C16 C18 61.4(2) . . . . ?
O3 S1 C16 C19 178.3(2) . . . . ?
N1 S1 C16 C17 57.3(2) . . . . ?
N1 S1 C16 C18 176.3(2) . . . . ?
N1 S1 C16 C19 -66.8(2) . . . . ?
N1 C7 C8 O1 -112.7(2) . . . . ?
N1 C7 C8 C9 127.5(2) . . . . ?
C1 O1 C8 C7 -12.2(3) . . . . ?
C1 O1 C8 C9 109.1(2) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C1 C6 C7 N1 113.9(2) . . . . ?
C1 C6 C7 C8 -6.2(3) . . . . ?
C2 C1 C6 C5 0.7(4) . . . . ?
C2 C1 C6 C7 -178.9(2) . . . . ?
C2 C3 C4 Cl1 -179.1(2) . . . . ?
C2 C3 C4 C5 1.0(4) . . . . ?
C3 C4 C5 C6 -1.7(4) . . . . ?
C4 C5 C6 C1 0.8(4) . . . . ?
C4 C5 C6 C7 -179.7(2) . . . . ?
C5 C6 C7 N1 -65.7(4) . . . . ?
C5 C6 C7 C8 174.3(3) . . . . ?
C6 C1 C2 Cl2 176.2(2) . . . . ?
C6 C1 C2 C3 -1.4(4) . . . . ?
C6 C7 C8 O1 11.0(2) . . . . ?
C6 C7 C8 C9 -108.8(2) . . . . ?
C7 C8 C9 O2 103.3(3) . . . . ?
C7 C8 C9 C10 -73.5(3) . . . . ?
C8 O1 C1 C2 -173.7(2) . . . . ?
C8 O1 C1 C6 8.5(3) . . . . ?
C8 C9 C10 C11 -3.3(4) . . . . ?
C8 C9 C10 C15 175.1(2) . . . . ?
C9 C10 C11 C12 177.6(3) . . . . ?
C9 C10 C15 C14 -177.0(2) . . . . ?
C10 C11 C12 C13 -0.1(4) . . . . ?
C11 C10 C15 C14 1.5(4) . . . . ?
C11 C12 C13 C14 0.3(4) . . . . ?
C12 C13 C14 C15 0.4(4) . . . . ?
C13 C14 C15 C10 -1.3(4) . . . . ?
C15 C10 C11 C12 -0.8(4) . . . . ?
C16 S1 N1 C7 166.1(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_m20170524d
_audit_block_doi                 10.5517/ccdc.csd.cc1q4x81
_database_code_depnum_ccdc_archive 'CCDC 1583643'
loop_
_audit_author_name
_audit_author_address
'minxuan zhang' 'nankai university'
_audit_update_record             
;
2017-11-02 deposited with the CCDC.	2019-04-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H21 N O3 S'
_chemical_formula_weight         343.43

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'
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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_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                   9.1621(2)
_cell_length_b                   11.5165(2)
_cell_length_c                   17.1645(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1811.10(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    11917
_cell_measurement_theta_min      2.1240
_cell_measurement_theta_max      31.0670

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9621
_exptl_absorpt_correction_T_max  0.9770
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 5.814
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            19767
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         30.90
_reflns_number_total             5059
_reflns_number_gt                4788
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0386P)²+0.2127P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(4)
_refine_ls_number_reflns         5059
_refine_ls_number_parameters     223
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0281
_refine_ls_wR_factor_ref         0.0710
_refine_ls_wR_factor_gt          0.0701
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.003
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.92712(3) 1.08884(2) -0.041440(16) 0.01863(6) Uani 1 1 d . . .
N1 N 0.86083(11) 0.95770(8) -0.02018(5) 0.01774(18) Uani 1 1 d D . .
H1 H 0.7870(12) 0.9313(12) -0.0494(7) 0.021 Uiso 1 1 d D . .
O1 O 1.12694(10) 0.67304(7) 0.10390(5) 0.02648(19) Uani 1 1 d . . .
O2 O 0.89711(10) 0.66720(7) 0.00982(5) 0.02416(19) Uani 1 1 d . . .
O3 O 0.96444(10) 1.09993(8) -0.12542(5) 0.0293(2) Uani 1 1 d . . .
C1 C 1.18084(14) 0.82982(11) 0.22480(7) 0.0231(2) Uani 1 1 d . . .
H1A H 1.2461 0.7663 0.2187 0.028 Uiso 1 1 calc R . .
C2 C 1.20284(15) 0.90928(12) 0.28404(7) 0.0280(3) Uani 1 1 d . . .
H2 H 1.2826 0.9002 0.3188 0.034 Uiso 1 1 calc R . .
C3 C 1.10817(16) 1.00224(12) 0.29251(8) 0.0314(3) Uani 1 1 d . . .
H3 H 1.1232 1.0565 0.3334 0.038 Uiso 1 1 calc R . .
C4 C 0.99191(17) 1.01678(12) 0.24188(8) 0.0337(3) Uani 1 1 d . . .
H4 H 0.9279 1.0811 0.2478 0.040 Uiso 1 1 calc R . .
C5 C 0.96912(15) 0.93721(11) 0.18241(7) 0.0260(3) Uani 1 1 d . . .
H5 H 0.8896 0.9471 0.1475 0.031 Uiso 1 1 calc R . .
C6 C 1.06303(13) 0.84258(9) 0.17383(6) 0.0190(2) Uani 1 1 d . . .
C7 C 1.04417(13) 0.75525(9) 0.11056(6) 0.0189(2) Uani 1 1 d . . .
C8 C 0.92156(14) 0.77380(9) 0.05164(6) 0.0185(2) Uani 1 1 d . . .
H8 H 0.8302 0.7993 0.0786 0.022 Uiso 1 1 calc R . .
C9 C 0.97239(13) 0.86773(9) -0.00864(6) 0.0172(2) Uani 1 1 d . . .
H9 H 1.0645 0.9047 0.0103 0.021 Uiso 1 1 calc R . .
C10 C 1.00619(13) 0.79142(9) -0.07813(6) 0.0185(2) Uani 1 1 d . . .
C11 C 1.06863(15) 0.81773(10) -0.14943(7) 0.0239(2) Uani 1 1 d . . .
H11 H 1.0975 0.8949 -0.1616 0.029 Uiso 1 1 calc R . .
C12 C 1.08801(17) 0.72760(12) -0.20316(7) 0.0305(3) Uani 1 1 d . . .
H12 H 1.1318 0.7435 -0.2522 0.037 Uiso 1 1 calc R . .
C13 C 1.04404(15) 0.61561(12) -0.18565(7) 0.0310(3) Uani 1 1 d . . .
H13 H 1.0588 0.5556 -0.2228 0.037 Uiso 1 1 calc R . .
C14 C 0.97881(15) 0.58917(11) -0.11477(7) 0.0265(2) Uani 1 1 d . . .
H14 H 0.9472 0.5126 -0.1030 0.032 Uiso 1 1 calc R . .
C15 C 0.96182(13) 0.67916(10) -0.06194(6) 0.0206(2) Uani 1 1 d . . .
C16 C 0.75807(13) 1.17276(9) -0.02701(7) 0.0207(2) Uani 1 1 d . . .
C17 C 0.72181(14) 1.16753(11) 0.05972(7) 0.0254(3) Uani 1 1 d . . .
H17A H 0.6929 1.0883 0.0736 0.038 Uiso 1 1 calc R . .
H17B H 0.6414 1.2210 0.0711 0.038 Uiso 1 1 calc R . .
H17C H 0.8079 1.1900 0.0901 0.038 Uiso 1 1 calc R . .
C18 C 0.79761(15) 1.29724(10) -0.05132(8) 0.0282(3) Uani 1 1 d . . .
H18A H 0.7130 1.3480 -0.0437 0.042 Uiso 1 1 calc R . .
H18B H 0.8260 1.2981 -0.1064 0.042 Uiso 1 1 calc R . .
H18C H 0.8792 1.3251 -0.0194 0.042 Uiso 1 1 calc R . .
C19 C 0.63772(15) 1.12622(11) -0.07971(8) 0.0287(3) Uani 1 1 d . . .
H19A H 0.5558 1.1809 -0.0802 0.043 Uiso 1 1 calc R . .
H19B H 0.6043 1.0509 -0.0601 0.043 Uiso 1 1 calc R . .
H19C H 0.6756 1.1169 -0.1327 0.043 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
S1 O3 1.4870(9) . ?
S1 N1 1.6682(10) . ?
S1 C16 1.8424(12) . ?
N1 C9 1.4688(15) . ?
N1 H1 0.895(8) . ?
O1 C7 1.2184(14) . ?
O2 C15 1.3738(14) . ?
O2 C8 1.4397(12) . ?
C1 C2 1.3828(17) . ?
C1 C6 1.3971(17) . ?
C1 H1A 0.9500 . ?
C2 C3 1.3855(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.385(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.3875(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.3963(16) . ?
C5 H5 0.9500 . ?
C6 C7 1.4903(15) . ?
C7 C8 1.5265(16) . ?
C8 C9 1.5677(14) . ?
C8 H8 1.0000 . ?
C9 C10 1.5135(15) . ?
C9 H9 1.0000 . ?
C10 C15 1.3835(16) . ?
C10 C11 1.3846(15) . ?
C11 C12 1.3998(17) . ?
C11 H11 0.9500 . ?
C12 C13 1.384(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.3892(19) . ?
C13 H13 0.9500 . ?
C14 C15 1.3859(16) . ?
C14 H14 0.9500 . ?
C16 C19 1.5236(17) . ?
C16 C17 1.5263(16) . ?
C16 C18 1.5364(16) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 N1 111.93(5) . . ?
O3 S1 C16 106.18(5) . . ?
N1 S1 C16 98.02(5) . . ?
C9 N1 S1 114.50(8) . . ?
C9 N1 H1 111.2(9) . . ?
S1 N1 H1 117.4(9) . . ?
C15 O2 C8 107.12(8) . . ?
C2 C1 C6 120.23(12) . . ?
C2 C1 H1A 119.9 . . ?
C6 C1 H1A 119.9 . . ?
C1 C2 C3 119.82(12) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 120.60(12) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.84(13) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 120.02(12) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 119.48(10) . . ?
C5 C6 C7 122.15(10) . . ?
C1 C6 C7 118.35(10) . . ?
O1 C7 C6 121.37(11) . . ?
O1 C7 C8 120.30(10) . . ?
C6 C7 C8 118.28(9) . . ?
O2 C8 C7 109.00(9) . . ?
O2 C8 C9 107.79(8) . . ?
C7 C8 C9 108.37(9) . . ?
O2 C8 H8 110.5 . . ?
C7 C8 H8 110.5 . . ?
C9 C8 H8 110.5 . . ?
N1 C9 C10 116.47(9) . . ?
N1 C9 C8 111.65(9) . . ?
C10 C9 C8 100.38(8) . . ?
N1 C9 H9 109.3 . . ?
C10 C9 H9 109.3 . . ?
C8 C9 H9 109.3 . . ?
C15 C10 C11 120.23(10) . . ?
C15 C10 C9 108.92(9) . . ?
C11 C10 C9 130.85(10) . . ?
C10 C11 C12 118.20(11) . . ?
C10 C11 H11 120.9 . . ?
C12 C11 H11 120.9 . . ?
C13 C12 C11 120.73(12) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 121.30(11) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C15 C14 C13 117.22(12) . . ?
C15 C14 H14 121.4 . . ?
C13 C14 H14 121.4 . . ?
O2 C15 C10 113.61(9) . . ?
O2 C15 C14 124.07(10) . . ?
C10 C15 C14 122.30(11) . . ?
C19 C16 C17 114.06(11) . . ?
C19 C16 C18 109.73(10) . . ?
C17 C16 C18 110.67(10) . . ?
C19 C16 S1 110.12(8) . . ?
C17 C16 S1 107.06(8) . . ?
C18 C16 S1 104.75(8) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
O3 S1 N1 C9 81.58(8) . . . . ?
C16 S1 N1 C9 -167.32(8) . . . . ?
C6 C1 C2 C3 -0.42(19) . . . . ?
C1 C2 C3 C4 -0.3(2) . . . . ?
C2 C3 C4 C5 0.5(2) . . . . ?
C3 C4 C5 C6 0.2(2) . . . . ?
C4 C5 C6 C1 -0.91(18) . . . . ?
C4 C5 C6 C7 -179.45(12) . . . . ?
C2 C1 C6 C5 1.04(17) . . . . ?
C2 C1 C6 C7 179.63(11) . . . . ?
C5 C6 C7 O1 -179.90(11) . . . . ?
C1 C6 C7 O1 1.55(16) . . . . ?
C5 C6 C7 C8 2.60(16) . . . . ?
C1 C6 C7 C8 -175.95(10) . . . . ?
C15 O2 C8 C7 -102.43(10) . . . . ?
C15 O2 C8 C9 14.99(12) . . . . ?
O1 C7 C8 O2 17.90(14) . . . . ?
C6 C7 C8 O2 -164.57(9) . . . . ?
O1 C7 C8 C9 -99.15(12) . . . . ?
C6 C7 C8 C9 78.37(11) . . . . ?
S1 N1 C9 C10 -96.63(10) . . . . ?
S1 N1 C9 C8 148.90(7) . . . . ?
O2 C8 C9 N1 110.73(10) . . . . ?
C7 C8 C9 N1 -131.45(9) . . . . ?
O2 C8 C9 C10 -13.35(11) . . . . ?
C7 C8 C9 C10 104.48(10) . . . . ?
N1 C9 C10 C15 -113.47(11) . . . . ?
C8 C9 C10 C15 7.21(12) . . . . ?
N1 C9 C10 C11 65.80(17) . . . . ?
C8 C9 C10 C11 -173.52(13) . . . . ?
C15 C10 C11 C12 -1.38(19) . . . . ?
C9 C10 C11 C12 179.42(13) . . . . ?
C10 C11 C12 C13 0.8(2) . . . . ?
C11 C12 C13 C14 0.4(2) . . . . ?
C12 C13 C14 C15 -1.02(19) . . . . ?
C8 O2 C15 C10 -10.72(13) . . . . ?
C8 O2 C15 C14 170.84(11) . . . . ?
C11 C10 C15 O2 -177.73(11) . . . . ?
C9 C10 C15 O2 1.63(14) . . . . ?
C11 C10 C15 C14 0.74(18) . . . . ?
C9 C10 C15 C14 -179.90(11) . . . . ?
C13 C14 C15 O2 178.78(11) . . . . ?
C13 C14 C15 C10 0.47(18) . . . . ?
O3 S1 C16 C19 58.23(10) . . . . ?
N1 S1 C16 C19 -57.46(9) . . . . ?
O3 S1 C16 C17 -177.26(8) . . . . ?
N1 S1 C16 C17 67.05(8) . . . . ?
O3 S1 C16 C18 -59.69(9) . . . . ?
N1 S1 C16 C18 -175.39(8) . . . . ?

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 H1 O1 0.895(8) 2.114(9) 2.9873(13) 164.8(13) 4_465

_diffrn_measured_fraction_theta_max 0.915
_diffrn_reflns_theta_full        30.90
_diffrn_measured_fraction_theta_full 0.915
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.039
