# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 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 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_170329h_0m
_audit_block_doi                 10.5517/ccdc.csd.cc212fbx
_database_code_depnum_ccdc_archive 'CCDC 1879168'
loop_
_audit_author_name
_audit_author_address
'Yang Jie'
;Wuhan University
China
;
_audit_update_record             
;
2018-11-15 deposited with the CCDC.	2019-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H19 N O2 S'
_chemical_formula_weight         301.39

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'

_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'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.377(3)
_cell_length_b                   9.712(3)
_cell_length_c                   13.362(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.331(4)
_cell_angle_gamma                90
_cell_volume                     1470.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6202
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      29.14

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      1.362
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.224
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            13816
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.250
_diffrn_reflns_theta_max         29.225
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3948
_reflns_number_gt                3437
_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    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0563P)²+0.6198P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3948
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.1111
_refine_ls_wR_factor_gt          0.0966
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_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
C1 C 0.58362(11) 0.17836(13) 0.50057(9) 0.0147(2) Uani 1 1 d . . . . .
C2 C 0.64774(11) 0.10922(15) 0.43020(10) 0.0187(3) Uani 1 1 d . . . . .
H2 H 0.6386 0.1364 0.3616 0.022 Uiso 1 1 calc R U . . .
C3 C 0.72385(11) 0.00213(15) 0.45983(10) 0.0204(3) Uani 1 1 d . . . . .
H3 H 0.7654 -0.0432 0.4108 0.024 Uiso 1 1 calc R U . . .
C4 C 0.74091(11) -0.04061(14) 0.55953(11) 0.0196(3) Uani 1 1 d . . . . .
H4 H 0.7931 -0.1143 0.5788 0.024 Uiso 1 1 calc R U . . .
C5 C 0.68017(11) 0.02650(13) 0.62979(10) 0.0165(2) Uani 1 1 d . . . . .
H5 H 0.6911 -0.0006 0.6983 0.020 Uiso 1 1 calc R U . . .
C6 C 0.60266(11) 0.13412(13) 0.60085(9) 0.0142(2) Uani 1 1 d . . . . .
C7 C 0.41805(11) 0.29665(13) 0.63150(9) 0.0146(2) Uani 1 1 d . . . . .
C8 C 0.32783(11) 0.33829(14) 0.68940(10) 0.0184(3) Uani 1 1 d . . . . .
H8 H 0.3312 0.3144 0.7585 0.022 Uiso 1 1 calc R U . . .
C9 C 0.23369(12) 0.41438(15) 0.64569(11) 0.0214(3) Uani 1 1 d . . . . .
H9 H 0.1721 0.4437 0.6842 0.026 Uiso 1 1 calc R U . . .
C10 C 0.23138(12) 0.44700(15) 0.54387(11) 0.0217(3) Uani 1 1 d . . . . .
H10 H 0.1675 0.4998 0.5134 0.026 Uiso 1 1 calc R U . . .
C11 C 0.31908(12) 0.40487(14) 0.48617(10) 0.0194(3) Uani 1 1 d . . . . .
H11 H 0.3139 0.4281 0.4168 0.023 Uiso 1 1 calc R U . . .
C12 C 0.41639(11) 0.32774(13) 0.52861(9) 0.0150(2) Uani 1 1 d . . . . .
C13 C 0.51203(12) 0.34585(14) 0.36998(9) 0.0179(3) Uani 1 1 d . . . . .
H13A H 0.5962 0.3511 0.3571 0.022 Uiso 1 1 calc R U . . .
H13B H 0.4815 0.4413 0.3710 0.022 Uiso 1 1 calc R U . . .
C14 C 0.44496(11) 0.26927(14) 0.28282(9) 0.0168(2) Uani 1 1 d . . . . .
H14A H 0.4615 0.1694 0.2892 0.020 Uiso 1 1 calc R U . . .
H14B H 0.3591 0.2831 0.2852 0.020 Uiso 1 1 calc R U . . .
C15 C 0.48148(11) 0.32118(14) 0.18253(9) 0.0159(2) Uani 1 1 d . . . . .
H15A H 0.5686 0.3182 0.1838 0.019 Uiso 1 1 calc R U . . .
H15B H 0.4563 0.4182 0.1730 0.019 Uiso 1 1 calc R U . . .
C16 C 0.42739(11) 0.23543(14) 0.09430(9) 0.0168(2) Uani 1 1 d . . . . .
H16A H 0.4467 0.1372 0.1070 0.020 Uiso 1 1 calc R U . . .
H16B H 0.3404 0.2450 0.0896 0.020 Uiso 1 1 calc R U . . .
C17 C 0.47138(13) 0.27809(16) -0.00553(10) 0.0223(3) Uani 1 1 d . . . . .
H17A H 0.4567 0.3766 -0.0167 0.033 Uiso 1 1 calc R U . . .
H17B H 0.4294 0.2253 -0.0602 0.033 Uiso 1 1 calc R U . . .
H17C H 0.5563 0.2598 -0.0038 0.033 Uiso 1 1 calc R U . . .
N1 N 0.50468(9) 0.28445(11) 0.47026(8) 0.0152(2) Uani 1 1 d . . . . .
O1 O 0.62200(9) 0.33490(12) 0.72875(8) 0.0290(3) Uani 1 1 d . . . . .
O2 O 0.50963(11) 0.13003(12) 0.77150(8) 0.0304(3) Uani 1 1 d . . . . .
S1 S 0.54284(3) 0.22447(3) 0.69564(2) 0.01702(10) 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
C1 N1 1.4017(17) . ?
C1 C6 1.4047(17) . ?
C1 C2 1.4124(17) . ?
C2 C3 1.387(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.3799(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.3986(18) . ?
C5 H5 0.9500 . ?
C6 S1 1.7313(13) . ?
C7 C8 1.4012(18) . ?
C7 C12 1.4060(17) . ?
C7 S1 1.7365(13) . ?
C8 C9 1.3848(19) . ?
C8 H8 0.9500 . ?
C9 C10 1.395(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.3785(19) . ?
C10 H10 0.9500 . ?
C11 C12 1.4112(18) . ?
C11 H11 0.9500 . ?
C12 N1 1.3925(16) . ?
C13 N1 1.4760(16) . ?
C13 C14 1.5254(18) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.5251(17) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.5257(18) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.5249(18) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
O1 S1 1.4433(11) . ?
O2 S1 1.4431(11) . ?

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
N1 C1 C6 122.58(11) . . ?
N1 C1 C2 120.92(11) . . ?
C6 C1 C2 116.50(12) . . ?
C3 C2 C1 120.91(12) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 121.65(12) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 118.44(12) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C4 C5 C6 120.51(12) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 121.98(11) . . ?
C5 C6 S1 117.20(9) . . ?
C1 C6 S1 120.43(10) . . ?
C8 C7 C12 122.27(12) . . ?
C8 C7 S1 116.83(10) . . ?
C12 C7 S1 120.36(10) . . ?
C9 C8 C7 119.91(12) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 118.44(12) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 H9 120.8 . . ?
C11 C10 C9 121.95(13) . . ?
C11 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
C10 C11 C12 120.95(12) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
N1 C12 C7 122.53(11) . . ?
N1 C12 C11 121.00(12) . . ?
C7 C12 C11 116.47(11) . . ?
N1 C13 C14 115.44(11) . . ?
N1 C13 H13A 108.4 . . ?
C14 C13 H13A 108.4 . . ?
N1 C13 H13B 108.4 . . ?
C14 C13 H13B 108.4 . . ?
H13A C13 H13B 107.5 . . ?
C15 C14 C13 110.60(10) . . ?
C15 C14 H14A 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C14 C15 C16 112.04(11) . . ?
C14 C15 H15A 109.2 . . ?
C16 C15 H15A 109.2 . . ?
C14 C15 H15B 109.2 . . ?
C16 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C17 C16 C15 112.71(11) . . ?
C17 C16 H16A 109.0 . . ?
C15 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
C15 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
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 . . ?
C12 N1 C1 122.43(10) . . ?
C12 N1 C13 119.41(11) . . ?
C1 N1 C13 118.06(10) . . ?
O2 S1 O1 116.98(8) . . ?
O2 S1 C6 109.76(7) . . ?
O1 S1 C6 108.92(6) . . ?
O2 S1 C7 110.36(7) . . ?
O1 S1 C7 108.04(7) . . ?
C6 S1 C7 101.68(6) . . ?

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 C3 -178.52(12) . . . . ?
C6 C1 C2 C3 0.90(18) . . . . ?
C1 C2 C3 C4 -0.6(2) . . . . ?
C2 C3 C4 C5 -0.2(2) . . . . ?
C3 C4 C5 C6 0.52(19) . . . . ?
C4 C5 C6 C1 -0.16(19) . . . . ?
C4 C5 C6 S1 -173.11(10) . . . . ?
N1 C1 C6 C5 178.86(11) . . . . ?
C2 C1 C6 C5 -0.55(18) . . . . ?
N1 C1 C6 S1 -8.41(17) . . . . ?
C2 C1 C6 S1 172.19(9) . . . . ?
C12 C7 C8 C9 -0.9(2) . . . . ?
S1 C7 C8 C9 170.66(11) . . . . ?
C7 C8 C9 C10 0.3(2) . . . . ?
C8 C9 C10 C11 0.5(2) . . . . ?
C9 C10 C11 C12 -0.8(2) . . . . ?
C8 C7 C12 N1 -178.78(12) . . . . ?
S1 C7 C12 N1 9.96(18) . . . . ?
C8 C7 C12 C11 0.61(19) . . . . ?
S1 C7 C12 C11 -170.66(10) . . . . ?
C10 C11 C12 N1 179.63(12) . . . . ?
C10 C11 C12 C7 0.23(19) . . . . ?
N1 C13 C14 C15 -166.83(11) . . . . ?
C13 C14 C15 C16 173.14(11) . . . . ?
C14 C15 C16 C17 -175.04(11) . . . . ?
C7 C12 N1 C1 17.44(18) . . . . ?
C11 C12 N1 C1 -161.91(12) . . . . ?
C7 C12 N1 C13 -166.31(11) . . . . ?
C11 C12 N1 C13 14.33(18) . . . . ?
C6 C1 N1 C12 -18.34(18) . . . . ?
C2 C1 N1 C12 161.05(12) . . . . ?
C6 C1 N1 C13 165.37(11) . . . . ?
C2 C1 N1 C13 -15.25(17) . . . . ?
C14 C13 N1 C12 -92.04(15) . . . . ?
C14 C13 N1 C1 84.37(14) . . . . ?
C5 C6 S1 O2 -41.78(12) . . . . ?
C1 C6 S1 O2 145.15(11) . . . . ?
C5 C6 S1 O1 87.47(11) . . . . ?
C1 C6 S1 O1 -85.60(11) . . . . ?
C5 C6 S1 C7 -158.63(10) . . . . ?
C1 C6 S1 C7 28.30(11) . . . . ?
C8 C7 S1 O2 42.75(12) . . . . ?
C12 C7 S1 O2 -145.52(11) . . . . ?
C8 C7 S1 O1 -86.27(11) . . . . ?
C12 C7 S1 O1 85.45(12) . . . . ?
C8 C7 S1 C6 159.17(10) . . . . ?
C12 C7 S1 C6 -29.10(12) . . . . ?

_refine_diff_density_max         0.387
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.070



####################################################################### 
# 
# 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_whu-2
_database_code_depnum_ccdc_archive 'CCDC 1879165'
loop_
_audit_author_name
_audit_author_address
'Yang Jie'
;Wuhan University
China
;
_audit_update_record             
;
2018-11-15 deposited with the CCDC.	2019-04-02 downloaded from the CCDC.
;
_audit_creation_date             2016-10-10
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_shelxl_version_number           2014-1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C14 H13 N O2 S'
_chemical_formula_sum            'C14 H13 N O2 S'
_chemical_formula_weight         259.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N S'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.9027(3)
_cell_length_b                   11.1576(4)
_cell_length_c                   13.5298(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.338(4)
_cell_angle_gamma                90
_cell_volume                     1190.97(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1739
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.9690
_cell_measurement_theta_min      5.1130
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.357
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91238
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'translucent light colourless'
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.13
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4385
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.065
_diffrn_reflns_theta_min         5.142
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3376
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -49.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6855   37.0000  150.0000 80

#__ type_ start__ end____ width___ exp.time_
  2 omega  -75.00   36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6855   19.0000  -90.0000 111

#__ type_ start__ end____ width___ exp.time_
  3 omega   24.00   71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6855 -125.0000   60.0000 47

#__ type_ start__ end____ width___ exp.time_
  4 omega   75.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8759   77.0000 -150.0000 103

#__ type_ start__ end____ width___ exp.time_
  5 omega   80.00  167.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8759   30.0000    0.0000 87

#__ type_ start__ end____ width___ exp.time_
  6 omega   35.00   61.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8759  -45.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega   73.00   99.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8759   77.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  8 omega   71.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8759  -45.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
  9 omega  135.00  176.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8759   77.0000 -180.0000 41

#__ type_ start__ end____ width___ exp.time_
 10 omega   31.00   86.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8759  -30.0000   90.0000 55

#__ type_ start__ end____ width___ exp.time_
 11 omega   39.00   87.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8759  -45.0000  -60.0000 48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1357788000
_diffrn_orient_matrix_UB_12      0.0991347000
_diffrn_orient_matrix_UB_13      0.0044302000
_diffrn_orient_matrix_UB_21      0.0250918000
_diffrn_orient_matrix_UB_22      -0.0171748000
_diffrn_orient_matrix_UB_23      -0.1110786000
_diffrn_orient_matrix_UB_31      -0.1382946000
_diffrn_orient_matrix_UB_32      0.0946130000
_diffrn_orient_matrix_UB_33      -0.0249305000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1714
_reflns_number_total             2127
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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         0.218
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0393
_refine_ls_restrained_S_all      1.039
_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)+(0.0540P)²+0.2870P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.1044
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_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
S1 S 0.23346(6) 0.64740(5) 0.67018(4) 0.01616(17) Uani 1 1 d . . . . .
O1 O 0.39973(19) 0.63394(14) 0.71966(12) 0.0209(4) Uani 1 1 d . . . . .
O2 O 0.0936(2) 0.66192(14) 0.73333(12) 0.0229(4) Uani 1 1 d . . . . .
N3 N 0.3303(2) 0.63179(16) 0.45528(13) 0.0154(4) Uani 1 1 d . . . . .
C4 C 0.3008(3) 0.74632(19) 0.49257(16) 0.0158(5) Uani 1 1 d . . . . .
C5 C 0.3290(3) 0.8498(2) 0.43554(17) 0.0208(5) Uani 1 1 d . . . . .
H5 H 0.3707 0.8419 0.3730 0.025 Uiso 1 1 calc R . . . .
C6 C 0.2642(3) 0.52822(19) 0.49626(16) 0.0151(4) Uani 1 1 d . . . . .
C7 C 0.1884(3) 0.3172(2) 0.48414(18) 0.0206(5) Uani 1 1 d . . . . .
H7 H 0.1874 0.2459 0.4485 0.025 Uiso 1 1 calc R . . . .
C8 C 0.2402(3) 0.7653(2) 0.58706(17) 0.0170(5) Uani 1 1 d . . . . .
C9 C 0.4119(3) 0.6227(2) 0.36019(16) 0.0180(5) Uani 1 1 d . . . . .
H9A H 0.4721 0.5471 0.3582 0.022 Uiso 1 1 calc R . . . .
H9B H 0.4946 0.6865 0.3566 0.022 Uiso 1 1 calc R . . . .
C10 C 0.1986(3) 0.52698(19) 0.59089(16) 0.0152(4) Uani 1 1 d . . . . .
C11 C 0.2872(3) 0.6305(2) 0.27005(17) 0.0229(5) Uani 1 1 d . . . . .
H11A H 0.3484 0.6286 0.2108 0.034 Uiso 1 1 calc GR . . . .
H11B H 0.2245 0.7040 0.2724 0.034 Uiso 1 1 calc GR . . . .
H11C H 0.2104 0.5639 0.2702 0.034 Uiso 1 1 calc GR . . . .
C12 C 0.2955(3) 0.9625(2) 0.47173(18) 0.0254(5) Uani 1 1 d . . . . .
H12 H 0.3175 1.0293 0.4334 0.030 Uiso 1 1 calc R . . . .
C13 C 0.1187(3) 0.3193(2) 0.57654(18) 0.0199(5) Uani 1 1 d . . . . .
H13 H 0.0694 0.2510 0.6018 0.024 Uiso 1 1 calc R . . . .
C14 C 0.2297(3) 0.9790(2) 0.56392(18) 0.0256(5) Uani 1 1 d . . . . .
H14 H 0.2047 1.0554 0.5863 0.031 Uiso 1 1 calc R . . . .
C15 C 0.2023(3) 0.8800(2) 0.62127(18) 0.0217(5) Uani 1 1 d . . . . .
H15 H 0.1584 0.8893 0.6831 0.026 Uiso 1 1 calc R . . . .
C16 C 0.2588(3) 0.4185(2) 0.44425(17) 0.0190(5) Uani 1 1 d . . . . .
H16 H 0.3032 0.4142 0.3822 0.023 Uiso 1 1 calc R . . . .
C17 C 0.1247(3) 0.4244(2) 0.62933(17) 0.0185(5) Uani 1 1 d . . . . .
H17 H 0.0792 0.4275 0.6911 0.022 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 O1 1.4474(16) . ?
S1 O2 1.4447(16) . ?
S1 C8 1.734(2) . ?
S1 C10 1.731(2) . ?
N3 C4 1.398(3) . ?
N3 C6 1.396(3) . ?
N3 C9 1.476(3) . ?
C4 C5 1.414(3) . ?
C4 C8 1.407(3) . ?
C5 H5 0.9300 . ?
C5 C12 1.381(3) . ?
C6 C10 1.409(3) . ?
C6 C16 1.412(3) . ?
C7 H7 0.9300 . ?
C7 C13 1.395(3) . ?
C7 C16 1.383(3) . ?
C8 C15 1.399(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C11 1.525(3) . ?
C10 C17 1.399(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12 0.9300 . ?
C12 C14 1.391(3) . ?
C13 H13 0.9300 . ?
C13 C17 1.373(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.374(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17 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 C8 108.51(10) . . ?
O1 S1 C10 108.26(9) . . ?
O2 S1 O1 116.30(10) . . ?
O2 S1 C8 110.61(10) . . ?
O2 S1 C10 110.73(10) . . ?
C10 S1 C8 101.35(11) . . ?
C4 N3 C9 117.90(18) . . ?
C6 N3 C4 122.60(18) . . ?
C6 N3 C9 118.81(18) . . ?
N3 C4 C5 120.97(19) . . ?
N3 C4 C8 122.57(19) . . ?
C8 C4 C5 116.5(2) . . ?
C4 C5 H5 119.6 . . ?
C12 C5 C4 120.7(2) . . ?
C12 C5 H5 119.6 . . ?
N3 C6 C10 122.34(19) . . ?
N3 C6 C16 121.4(2) . . ?
C10 C6 C16 116.3(2) . . ?
C13 C7 H7 119.2 . . ?
C16 C7 H7 119.2 . . ?
C16 C7 C13 121.7(2) . . ?
C4 C8 S1 119.98(17) . . ?
C15 C8 S1 117.66(18) . . ?
C15 C8 C4 122.0(2) . . ?
N3 C9 H9A 108.9 . . ?
N3 C9 H9B 108.9 . . ?
N3 C9 C11 113.50(17) . . ?
H9A C9 H9B 107.7 . . ?
C11 C9 H9A 108.9 . . ?
C11 C9 H9B 108.9 . . ?
C6 C10 S1 120.12(17) . . ?
C17 C10 S1 117.34(17) . . ?
C17 C10 C6 122.0(2) . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C5 C12 H12 119.1 . . ?
C5 C12 C14 121.8(2) . . ?
C14 C12 H12 119.1 . . ?
C7 C13 H13 120.8 . . ?
C17 C13 C7 118.5(2) . . ?
C17 C13 H13 120.8 . . ?
C12 C14 H14 120.7 . . ?
C15 C14 C12 118.7(2) . . ?
C15 C14 H14 120.7 . . ?
C8 C15 H15 119.9 . . ?
C14 C15 C8 120.3(2) . . ?
C14 C15 H15 119.9 . . ?
C6 C16 H16 119.5 . . ?
C7 C16 C6 121.0(2) . . ?
C7 C16 H16 119.5 . . ?
C10 C17 H17 119.7 . . ?
C13 C17 C10 120.5(2) . . ?
C13 C17 H17 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C8 C15 C14 170.34(18) . . . . ?
S1 C10 C17 C13 -169.21(16) . . . . ?
O1 S1 C8 C4 82.87(19) . . . . ?
O1 S1 C8 C15 -90.04(18) . . . . ?
O1 S1 C10 C6 -82.45(19) . . . . ?
O1 S1 C10 C17 89.10(18) . . . . ?
O2 S1 C8 C4 -148.44(17) . . . . ?
O2 S1 C8 C15 38.6(2) . . . . ?
O2 S1 C10 C6 148.96(17) . . . . ?
O2 S1 C10 C17 -39.49(19) . . . . ?
N3 C4 C5 C12 178.3(2) . . . . ?
N3 C4 C8 S1 11.0(3) . . . . ?
N3 C4 C8 C15 -176.4(2) . . . . ?
N3 C6 C10 S1 -12.2(3) . . . . ?
N3 C6 C10 C17 176.66(19) . . . . ?
N3 C6 C16 C7 -178.0(2) . . . . ?
C4 N3 C6 C10 -15.8(3) . . . . ?
C4 N3 C6 C16 163.90(19) . . . . ?
C4 N3 C9 C11 -85.5(2) . . . . ?
C4 C5 C12 C14 -1.4(4) . . . . ?
C4 C8 C15 C14 -2.4(3) . . . . ?
C5 C4 C8 S1 -169.75(16) . . . . ?
C5 C4 C8 C15 2.8(3) . . . . ?
C5 C12 C14 C15 1.9(4) . . . . ?
C6 N3 C4 C5 -162.8(2) . . . . ?
C6 N3 C4 C8 16.4(3) . . . . ?
C6 N3 C9 C11 85.2(2) . . . . ?
C6 C10 C17 C13 2.2(3) . . . . ?
C7 C13 C17 C10 0.2(3) . . . . ?
C8 S1 C10 C6 31.58(19) . . . . ?
C8 S1 C10 C17 -156.87(17) . . . . ?
C8 C4 C5 C12 -0.9(3) . . . . ?
C9 N3 C4 C5 7.5(3) . . . . ?
C9 N3 C4 C8 -173.27(19) . . . . ?
C9 N3 C6 C10 173.97(19) . . . . ?
C9 N3 C6 C16 -6.4(3) . . . . ?
C10 S1 C8 C4 -31.0(2) . . . . ?
C10 S1 C8 C15 156.11(17) . . . . ?
C10 C6 C16 C7 1.7(3) . . . . ?
C12 C14 C15 C8 0.0(4) . . . . ?
C13 C7 C16 C6 0.6(3) . . . . ?
C16 C6 C10 S1 168.12(16) . . . . ?
C16 C6 C10 C17 -3.0(3) . . . . ?
C16 C7 C13 C17 -1.5(3) . . . . ?

_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_wd-7
_database_code_depnum_ccdc_archive 'CCDC 1879164'
loop_
_audit_author_name
_audit_author_address
'Yang Jie'
;Wuhan University
China
;
_audit_update_record             
;
2018-11-15 deposited with the CCDC.	2019-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H11 N O2 S'
_chemical_formula_weight         245.29

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           Monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.78316(19)
_cell_length_b                   11.4642(2)
_cell_length_c                   11.1048(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.3006(19)
_cell_angle_gamma                90.00
_cell_volume                     1117.88(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    295.04(10)
_cell_measurement_reflns_used    3988
_cell_measurement_theta_min      3.7940
_cell_measurement_theta_max      73.8330

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_absorpt_coefficient_mu    0.277
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.48921
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295.04(10)
_diffrn_radiation_wavelength     0.71000
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_detector                 'CCD plate'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6290
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0204
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.55
_diffrn_reflns_theta_max         26.27
_reflns_number_total             2205
_reflns_number_gt                2028
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.1140P)²+0.1530P] 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_number_reflns         2205
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0742
_refine_ls_wR_factor_ref         0.1708
_refine_ls_wR_factor_gt          0.1665
_refine_ls_goodness_of_fit_ref   1.197
_refine_ls_restrained_S_all      1.197
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.80887(5) 0.57428(4) 0.19192(4) 0.0395(2) Uani 1 1 d . . .
O1 O 0.9093(2) 0.48142(17) 0.1588(2) 0.0687(6) Uani 1 1 d . . .
O2 O 0.8278(2) 0.62062(17) 0.31183(14) 0.0546(5) Uani 1 1 d . . .
N1 N 0.5535(2) 0.73443(16) 0.12263(17) 0.0438(4) Uani 1 1 d . . .
C1 C 0.9567(3) 0.7101(3) 0.0335(2) 0.0551(6) Uani 1 1 d . . .
H1 H 1.0363 0.6569 0.0409 0.066 Uiso 1 1 calc R . .
C2 C 0.8200(2) 0.68912(17) 0.09042(18) 0.0385(4) Uani 1 1 d . . .
C3 C 0.6944(2) 0.76260(17) 0.07569(17) 0.0387(5) Uani 1 1 d . . .
C4 C 0.7164(3) 0.8643(2) 0.0075(2) 0.0573(6) Uani 1 1 d . . .
H4 H 0.6368 0.9172 -0.0027 0.069 Uiso 1 1 calc R . .
C5 C 0.8543(4) 0.8866(3) -0.0443(3) 0.0720(9) Uani 1 1 d . . .
H5 H 0.8670 0.9553 -0.0874 0.086 Uiso 1 1 calc R . .
C6 C 0.9734(4) 0.8096(3) -0.0336(2) 0.0718(9) Uani 1 1 d . . .
H6 H 1.0647 0.8247 -0.0715 0.086 Uiso 1 1 calc R . .
C7 C 0.6210(2) 0.53238(19) 0.16995(17) 0.0404(5) Uani 1 1 d . . .
C8 C 0.5817(4) 0.4156(2) 0.1857(2) 0.0561(7) Uani 1 1 d . . .
H8 H 0.6565 0.3597 0.2005 0.067 Uiso 1 1 calc R . .
C9 C 0.4300(4) 0.3843(3) 0.1789(2) 0.0739(10) Uani 1 1 d . . .
H9 H 0.4018 0.3068 0.1898 0.089 Uiso 1 1 calc R . .
C10 C 0.3205(4) 0.4679(4) 0.1559(2) 0.0737(10) Uani 1 1 d . . .
H10 H 0.2184 0.4464 0.1527 0.088 Uiso 1 1 calc R . .
C11 C 0.3596(3) 0.5823(3) 0.1377(2) 0.0603(7) Uani 1 1 d . . .
H11 H 0.2835 0.6368 0.1211 0.072 Uiso 1 1 calc R . .
C12 C 0.5122(2) 0.6187(2) 0.14361(17) 0.0412(5) Uani 1 1 d . . .
C13 C 0.4337(3) 0.8234(3) 0.1188(3) 0.0671(8) Uani 1 1 d . . .
H13A H 0.4782 0.8989 0.1324 0.101 Uiso 1 1 calc R . .
H13B H 0.3613 0.8075 0.1802 0.101 Uiso 1 1 calc R . .
H13C H 0.3830 0.8222 0.0413 0.101 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 O1 1.4359(17) . ?
S1 O2 1.4397(17) . ?
S1 C7 1.730(2) . ?
S1 C2 1.737(2) . ?
N1 C3 1.392(3) . ?
N1 C12 1.396(3) . ?
N1 C13 1.466(3) . ?
C1 C6 1.373(4) . ?
C1 C2 1.390(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.394(3) . ?
C3 C4 1.406(3) . ?
C4 C5 1.377(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.372(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.394(3) . ?
C7 C12 1.403(3) . ?
C8 C9 1.380(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.378(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.372(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.404(3) . ?
C11 H11 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 116.88(12) . . ?
O1 S1 C7 110.33(12) . . ?
O2 S1 C7 108.81(10) . . ?
O1 S1 C2 110.58(11) . . ?
O2 S1 C2 108.26(10) . . ?
C7 S1 C2 100.74(10) . . ?
C3 N1 C12 121.33(17) . . ?
C3 N1 C13 118.1(2) . . ?
C12 N1 C13 118.5(2) . . ?
C6 C1 C2 119.7(3) . . ?
C6 C1 H1 120.2 . . ?
C2 C1 H1 120.2 . . ?
C1 C2 C3 122.1(2) . . ?
C1 C2 S1 119.19(18) . . ?
C3 C2 S1 118.55(15) . . ?
N1 C3 C2 121.57(18) . . ?
N1 C3 C4 121.9(2) . . ?
C2 C3 C4 116.5(2) . . ?
C5 C4 C3 120.8(3) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C6 C5 C4 121.4(3) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C1 119.4(3) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
C8 C7 C12 122.3(2) . . ?
C8 C7 S1 119.14(19) . . ?
C12 C7 S1 118.48(16) . . ?
C9 C8 C7 119.0(3) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C10 C9 C8 119.9(3) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C11 C10 C9 121.1(3) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 121.3(3) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
N1 C12 C7 121.76(18) . . ?
N1 C12 C11 121.8(2) . . ?
C7 C12 C11 116.5(2) . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
C6 C1 C2 C3 4.1(4) . . . . ?
C6 C1 C2 S1 -170.9(2) . . . . ?
O1 S1 C2 C1 -30.8(2) . . . . ?
O2 S1 C2 C1 98.40(19) . . . . ?
C7 S1 C2 C1 -147.51(18) . . . . ?
O1 S1 C2 C3 153.93(18) . . . . ?
O2 S1 C2 C3 -76.83(18) . . . . ?
C7 S1 C2 C3 37.26(18) . . . . ?
C12 N1 C3 C2 -25.4(3) . . . . ?
C13 N1 C3 C2 171.2(2) . . . . ?
C12 N1 C3 C4 152.4(2) . . . . ?
C13 N1 C3 C4 -11.1(3) . . . . ?
C1 C2 C3 N1 173.1(2) . . . . ?
S1 C2 C3 N1 -11.8(3) . . . . ?
C1 C2 C3 C4 -4.7(3) . . . . ?
S1 C2 C3 C4 170.36(16) . . . . ?
N1 C3 C4 C5 -175.9(2) . . . . ?
C2 C3 C4 C5 1.9(3) . . . . ?
C3 C4 C5 C6 1.5(4) . . . . ?
C4 C5 C6 C1 -2.2(4) . . . . ?
C2 C1 C6 C5 -0.5(4) . . . . ?
O1 S1 C7 C8 32.2(2) . . . . ?
O2 S1 C7 C8 -97.30(19) . . . . ?
C2 S1 C7 C8 149.02(18) . . . . ?
O1 S1 C7 C12 -151.46(17) . . . . ?
O2 S1 C7 C12 79.08(18) . . . . ?
C2 S1 C7 C12 -34.59(18) . . . . ?
C12 C7 C8 C9 -2.1(3) . . . . ?
S1 C7 C8 C9 174.17(18) . . . . ?
C7 C8 C9 C10 0.5(4) . . . . ?
C8 C9 C10 C11 1.0(4) . . . . ?
C9 C10 C11 C12 -1.0(4) . . . . ?
C3 N1 C12 C7 28.3(3) . . . . ?
C13 N1 C12 C7 -168.4(2) . . . . ?
C3 N1 C12 C11 -150.8(2) . . . . ?
C13 N1 C12 C11 12.6(3) . . . . ?
C8 C7 C12 N1 -177.0(2) . . . . ?
S1 C7 C12 N1 6.7(3) . . . . ?
C8 C7 C12 C11 2.1(3) . . . . ?
S1 C7 C12 C11 -174.21(16) . . . . ?
C10 C11 C12 N1 178.6(2) . . . . ?
C10 C11 C12 C7 -0.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        26.27
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.479
_refine_diff_density_min         -1.056
_refine_diff_density_rms         0.252
####################################################################### 
# 
# 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_whu-4
_database_code_depnum_ccdc_archive 'CCDC 1879167'
loop_
_audit_author_name
_audit_author_address
'Yang Jie'
;Wuhan University
China
;
_audit_update_record             
;
2018-11-15 deposited with the CCDC.	2019-04-02 downloaded from the CCDC.
;
_audit_creation_date             2016-10-10
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_shelxl_version_number           2014-1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H17 N O2 S'
_chemical_formula_sum            'C16 H17 N O2 S'
_chemical_formula_weight         287.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N S'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   18.9325(7)
_cell_length_b                   9.4253(3)
_cell_length_c                   17.2146(6)
_cell_angle_alpha                90
_cell_angle_beta                 114.976(4)
_cell_angle_gamma                90
_cell_volume                     2784.58(19)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2387
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.7060
_cell_measurement_theta_min      5.1390
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.069
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94229
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_av_unetI/netI     0.0773
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10351
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.052
_diffrn_reflns_theta_min         5.142
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3376
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -122.00   -4.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5605  -19.0000   30.0000 118

#__ type_ start__ end____ width___ exp.time_
  2 omega  -37.00   27.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5605   37.0000 -150.0000 64

#__ type_ start__ end____ width___ exp.time_
  3 omega   31.00   57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.5605 -125.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega   46.00   72.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8759  -30.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega   39.00   98.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8759  -45.0000    0.0000 59

#__ type_ start__ end____ width___ exp.time_
  6 omega   49.00   90.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8759  -30.0000  120.0000 41

#__ type_ start__ end____ width___ exp.time_
  7 omega  126.00  168.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8759   61.0000 -180.0000 42

#__ type_ start__ end____ width___ exp.time_
  8 omega   69.00   98.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8759  -45.0000   30.0000 29

#__ type_ start__ end____ width___ exp.time_
  9 omega   79.00  177.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8759   30.0000  -90.0000 98

#__ type_ start__ end____ width___ exp.time_
 10 omega   58.00   84.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8759  -30.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega   78.00  176.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8759   61.0000  150.0000 98

#__ type_ start__ end____ width___ exp.time_
 12 omega   32.00   59.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8759  -30.0000 -120.0000 27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0821982000
_diffrn_orient_matrix_UB_12      -0.0189721000
_diffrn_orient_matrix_UB_13      0.0038343000
_diffrn_orient_matrix_UB_21      -0.0294301000
_diffrn_orient_matrix_UB_22      -0.1258797000
_diffrn_orient_matrix_UB_23      -0.0626631000
_diffrn_orient_matrix_UB_31      -0.0207061000
_diffrn_orient_matrix_UB_32      0.1026613000
_diffrn_orient_matrix_UB_33      -0.0761505000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3557
_reflns_number_total             4979
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         4979
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0435
_refine_ls_restrained_S_all      0.956
_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)+(0.0340P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.1002
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C34(H34A,H34B), C81(H81A,H81B), C90(H90A,H90B), C104(H10A,H10B),
 C105(H10C,H10D)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C24(H24), C32(H32), C48(H48), C51(H51), C66(H66), C70(H70),
 C75(H75), C78(H78), C79(H79), C84(H84), C92(H92), C94(H94), C110(H110),
 C119(H119), C121(H121)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C67(H67A,H67B,H67C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
S6 S 0.44145(3) 0.72420(7) 0.33462(4) 0.01599(14) Uani 1 1 d . . . . .
S8 S 1.06891(3) 0.73001(7) 0.39666(4) 0.01626(14) Uani 1 1 d . . . . .
O8 O 1.12698(11) 0.6441(2) 0.38526(13) 0.0262(4) Uani 1 1 d . . . . .
O9 O 0.38635(11) 0.6362(2) 0.26842(12) 0.0265(5) Uani 1 1 d . . . . .
O11 O 1.04484(11) 0.8584(2) 0.34595(12) 0.0226(4) Uani 1 1 d . . . . .
O15 O 0.46853(11) 0.8497(2) 0.30687(11) 0.0236(4) Uani 1 1 d . . . . .
N20 N 0.53582(12) 0.7735(2) 0.52398(13) 0.0152(4) Uani 1 1 d . . . . .
N3 N 0.96414(12) 0.7764(2) 0.48608(13) 0.0153(4) Uani 1 1 d . . . . .
C2 C 0.52144(14) 0.6254(3) 0.40057(15) 0.0141(5) Uani 1 1 d . . . . .
C7 C 0.90680(14) 0.8300(3) 0.51636(16) 0.0169(5) Uani 1 1 d . . . . .
H7A H 0.8561 0.8351 0.4680 0.020 Uiso 1 1 calc R . . . .
H7B H 0.9214 0.9256 0.5382 0.020 Uiso 1 1 calc R . . . .
C12 C 0.63517(14) 0.5996(3) 0.53279(16) 0.0175(5) Uani 1 1 d . . . . .
H12 H 0.6652 0.6247 0.5895 0.021 Uiso 1 1 calc R . . . .
C18 C 0.83163(15) 0.7016(3) 0.68165(16) 0.0223(6) Uani 1 1 d . . . . .
H18A H 0.8191 0.6059 0.6612 0.033 Uiso 1 1 calc GR . . . .
H18B H 0.7917 0.7379 0.6967 0.033 Uiso 1 1 calc GR . . . .
H18C H 0.8807 0.7028 0.7311 0.033 Uiso 1 1 calc GR . . . .
C19 C 1.09940(14) 0.7772(3) 0.50340(15) 0.0162(5) Uani 1 1 d . . . . .
C22 C 0.98656(14) 0.6317(3) 0.38021(16) 0.0155(5) Uani 1 1 d . . . . .
C24 C 0.66153(15) 0.4950(3) 0.49535(17) 0.0203(5) Uani 1 1 d . . . . .
H24 H 0.7096 0.4527 0.5271 0.024 Uiso 1 1 calc R . . . .
C25 C 0.40445(14) 0.7775(3) 0.40666(15) 0.0154(5) Uani 1 1 d . . . . .
C32 C 0.32509(15) 0.8059(3) 0.37558(16) 0.0191(5) Uani 1 1 d . . . . .
H32 H 0.2917 0.7786 0.3202 0.023 Uiso 1 1 calc R . . . .
C34 C 0.59012(14) 0.8317(3) 0.60741(15) 0.0172(5) Uani 1 1 d . . . . .
H34A H 0.5739 0.9275 0.6126 0.021 Uiso 1 1 calc R . . . .
H34B H 0.6416 0.8374 0.6083 0.021 Uiso 1 1 calc R . . . .
C38 C 1.04249(14) 0.8116(3) 0.53297(15) 0.0153(5) Uani 1 1 d . . . . .
C48 C 0.86865(14) 0.6013(3) 0.39791(16) 0.0175(5) Uani 1 1 d . . . . .
H48 H 0.8359 0.6252 0.4237 0.021 Uiso 1 1 calc R . . . .
C51 C 0.42686(15) 0.8850(3) 0.54158(16) 0.0189(5) Uani 1 1 d . . . . .
H51 H 0.4598 0.9127 0.5970 0.023 Uiso 1 1 calc R . . . .
C53 C 0.45764(15) 0.8120(3) 0.49133(15) 0.0149(5) Uani 1 1 d . . . . .
C63 C 0.56357(14) 0.6691(3) 0.48669(15) 0.0146(5) Uani 1 1 d . . . . .
C66 C 0.54766(15) 0.5177(3) 0.36399(16) 0.0177(5) Uani 1 1 d . . . . .
H66 H 0.5178 0.4905 0.3076 0.021 Uiso 1 1 calc R . . . .
C67 C 0.67053(15) 0.7133(3) 0.84488(16) 0.0235(6) Uani 1 1 d . . . . .
H67A H 0.6917 0.6230 0.8398 0.035 Uiso 1 1 calc GR . . . .
H67B H 0.6213 0.6992 0.8475 0.035 Uiso 1 1 calc GR . . . .
H67C H 0.7059 0.7599 0.8962 0.035 Uiso 1 1 calc GR . . . .
C70 C 0.29593(15) 0.8741(3) 0.42644(17) 0.0210(6) Uani 1 1 d . . . . .
H70 H 0.2429 0.8921 0.4064 0.025 Uiso 1 1 calc R . . . .
C75 C 0.96382(15) 0.5247(3) 0.31789(15) 0.0178(5) Uani 1 1 d . . . . .
H75 H 0.9959 0.5001 0.2914 0.021 Uiso 1 1 calc R . . . .
C78 C 0.84618(15) 0.4972(3) 0.33602(16) 0.0209(6) Uani 1 1 d . . . . .
H78 H 0.7982 0.4531 0.3205 0.025 Uiso 1 1 calc R . . . .
C79 C 0.89353(16) 0.4558(3) 0.29590(16) 0.0206(6) Uani 1 1 d . . . . .
H79 H 0.8781 0.3835 0.2553 0.025 Uiso 1 1 calc R . . . .
C81 C 0.59558(14) 0.7458(3) 0.68511(15) 0.0178(5) Uani 1 1 d . . . . .
H81A H 0.5459 0.7487 0.6888 0.021 Uiso 1 1 calc R . . . .
H81B H 0.6072 0.6476 0.6782 0.021 Uiso 1 1 calc R . . . .
C84 C 1.14716(17) 0.9057(3) 0.66032(17) 0.0238(6) Uani 1 1 d . . . . .
H84 H 1.1631 0.9520 0.7127 0.029 Uiso 1 1 calc R . . . .
C90 C 0.65880(14) 0.8051(3) 0.76712(15) 0.0184(5) Uani 1 1 d . . . . .
H90A H 0.6447 0.9005 0.7763 0.022 Uiso 1 1 calc R . . . .
H90B H 0.7074 0.8104 0.7611 0.022 Uiso 1 1 calc R . . . .
C92 C 1.17854(15) 0.7992(3) 0.55278(17) 0.0207(6) Uani 1 1 d . . . . .
H92 H 1.2147 0.7714 0.5323 0.025 Uiso 1 1 calc R . . . .
C94 C 0.61791(15) 0.4511(3) 0.41101(17) 0.0196(5) Uani 1 1 d . . . . .
H94 H 0.6357 0.3788 0.3871 0.024 Uiso 1 1 calc R . . . .
C104 C 0.83687(14) 0.7932(3) 0.61182(15) 0.0195(5) Uani 1 1 d . . . . .
H10A H 0.8485 0.8902 0.6321 0.023 Uiso 1 1 calc R . . . .
H10B H 0.7870 0.7929 0.5621 0.023 Uiso 1 1 calc R . . . .
C105 C 0.89994(14) 0.7393(3) 0.58600(16) 0.0172(5) Uani 1 1 d . . . . .
H10C H 0.9496 0.7389 0.6360 0.021 Uiso 1 1 calc R . . . .
H10D H 0.8880 0.6425 0.5656 0.021 Uiso 1 1 calc R . . . .
C110 C 1.20346(15) 0.8628(3) 0.63264(18) 0.0240(6) Uani 1 1 d . . . . .
H110 H 1.2562 0.8766 0.6669 0.029 Uiso 1 1 calc R . . . .
C112 C 0.94026(14) 0.6721(3) 0.42275(15) 0.0145(5) Uani 1 1 d . . . . .
C119 C 1.06914(16) 0.8816(3) 0.61285(17) 0.0212(6) Uani 1 1 d . . . . .
H119 H 1.0335 0.9116 0.6335 0.025 Uiso 1 1 calc R . . . .
C121 C 0.34786(16) 0.9159(3) 0.50908(17) 0.0220(6) Uani 1 1 d . . . . .
H121 H 0.3289 0.9655 0.5430 0.026 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
S6 O9 1.4391(19) . ?
S6 O15 1.448(2) . ?
S6 C2 1.731(2) . ?
S6 C25 1.736(3) . ?
S8 O8 1.444(2) . ?
S8 O11 1.4481(19) . ?
S8 C19 1.735(2) . ?
S8 C22 1.731(3) . ?
N20 C34 1.475(3) . ?
N20 C53 1.392(3) . ?
N20 C63 1.393(3) . ?
N3 C7 1.478(3) . ?
N3 C38 1.397(3) . ?
N3 C112 1.394(3) . ?
C2 C63 1.416(3) . ?
C2 C66 1.391(4) . ?
C7 C105 1.522(3) . ?
C12 C24 1.381(4) . ?
C12 C63 1.410(4) . ?
C18 C104 1.517(4) . ?
C19 C38 1.410(4) . ?
C19 C92 1.391(4) . ?
C22 C75 1.401(4) . ?
C22 C112 1.411(4) . ?
C24 C94 1.396(4) . ?
C25 C32 1.392(4) . ?
C25 C53 1.416(3) . ?
C32 C70 1.376(4) . ?
C34 C81 1.529(3) . ?
C38 C119 1.412(4) . ?
C48 C78 1.377(4) . ?
C48 C112 1.406(4) . ?
C51 C53 1.409(4) . ?
C51 C121 1.389(4) . ?
C66 C94 1.382(4) . ?
C67 C90 1.529(4) . ?
C70 C121 1.402(4) . ?
C75 C79 1.382(4) . ?
C78 C79 1.398(4) . ?
C81 C90 1.520(3) . ?
C84 C110 1.398(4) . ?
C84 C119 1.372(4) . ?
C92 C110 1.387(4) . ?
C104 C105 1.526(3) . ?

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
O9 S6 O15 116.66(12) . . ?
O9 S6 C2 110.49(12) . . ?
O9 S6 C25 110.86(12) . . ?
O15 S6 C2 108.80(12) . . ?
O15 S6 C25 107.78(12) . . ?
C2 S6 C25 101.08(12) . . ?
O8 S8 O11 116.77(12) . . ?
O8 S8 C19 110.83(12) . . ?
O8 S8 C22 111.24(13) . . ?
O11 S8 C19 107.67(12) . . ?
O11 S8 C22 108.43(12) . . ?
C22 S8 C19 100.62(12) . . ?
C53 N20 C34 118.8(2) . . ?
C53 N20 C63 122.8(2) . . ?
C63 N20 C34 117.9(2) . . ?
C38 N3 C7 118.3(2) . . ?
C112 N3 C7 118.2(2) . . ?
C112 N3 C38 122.3(2) . . ?
C63 C2 S6 118.7(2) . . ?
C66 C2 S6 118.42(19) . . ?
C66 C2 C63 122.4(2) . . ?
N3 C7 C105 113.9(2) . . ?
C24 C12 C63 121.3(2) . . ?
C38 C19 S8 118.55(18) . . ?
C92 C19 S8 118.4(2) . . ?
C92 C19 C38 122.3(2) . . ?
C75 C22 S8 118.4(2) . . ?
C75 C22 C112 122.3(2) . . ?
C112 C22 S8 119.0(2) . . ?
C12 C24 C94 121.7(2) . . ?
C32 C25 S6 118.47(19) . . ?
C32 C25 C53 122.3(2) . . ?
C53 C25 S6 118.40(19) . . ?
C70 C32 C25 120.2(2) . . ?
N20 C34 C81 114.6(2) . . ?
N3 C38 C19 121.6(2) . . ?
N3 C38 C119 121.9(2) . . ?
C19 C38 C119 116.5(2) . . ?
C78 C48 C112 121.1(2) . . ?
C121 C51 C53 120.6(2) . . ?
N20 C53 C25 121.9(2) . . ?
N20 C53 C51 121.6(2) . . ?
C51 C53 C25 116.4(2) . . ?
N20 C63 C2 122.2(2) . . ?
N20 C63 C12 121.9(2) . . ?
C12 C63 C2 115.9(2) . . ?
C94 C66 C2 120.4(2) . . ?
C32 C70 C121 118.6(2) . . ?
C79 C75 C22 119.8(2) . . ?
C48 C78 C79 121.9(2) . . ?
C75 C79 C78 118.5(2) . . ?
C90 C81 C34 110.7(2) . . ?
C119 C84 C110 122.2(3) . . ?
C81 C90 C67 111.8(2) . . ?
C110 C92 C19 119.9(3) . . ?
C66 C94 C24 118.4(3) . . ?
C18 C104 C105 111.2(2) . . ?
C7 C105 C104 112.3(2) . . ?
C92 C110 C84 118.2(2) . . ?
N3 C112 C22 121.9(2) . . ?
N3 C112 C48 121.7(2) . . ?
C48 C112 C22 116.4(2) . . ?
C84 C119 C38 120.6(3) . . ?
C51 C121 C70 121.6(3) . . ?

_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_mo_170322j_0m
_database_code_depnum_ccdc_archive 'CCDC 1879169'
loop_
_audit_author_name
_audit_author_address
'Yang Jie'
;Wuhan University
China
;
_audit_update_record             
;
2018-11-15 deposited with the CCDC.	2019-04-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H21 N O2 S'
_chemical_formula_weight         315.42

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'

_space_group_crystal_system      trigonal
_space_group_IT_number           161
_space_group_name_H-M_alt        'R 3 c :H'
_space_group_name_Hall           'R 3 -2"c'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z+1/2'
'-x+y, y, z+1/2'
'x, x-y, z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-y+2/3, -x+1/3, z+5/6'
'-x+y+2/3, y+1/3, z+5/6'
'x+2/3, x-y+1/3, z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-y+1/3, -x+2/3, z+7/6'
'-x+y+1/3, y+2/3, z+7/6'
'x+1/3, x-y+2/3, z+7/6'

_cell_length_a                   26.477(7)
_cell_length_b                   26.477(7)
_cell_length_c                   12.475(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     7574(4)
_cell_formula_units_Z            18
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1607
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      18.37

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      1.245
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_F_000             3024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.199
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            18252
_diffrn_reflns_av_unetI/netI     0.0705
_diffrn_reflns_av_R_equivalents  0.0914
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.538
_diffrn_reflns_theta_max         25.623
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3172
_reflns_number_gt                1926
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.979
_reflns_Friedel_fraction_max     0.988
_reflns_Friedel_fraction_full    0.988

_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    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0726P)²+0.5945P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 719 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.10(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3172
_refine_ls_number_parameters     200
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.1104
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1427
_refine_ls_wR_factor_gt          0.1176
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_restrained_S_all      0.995
_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
C1 C 0.5945(3) 0.6458(3) 0.8219(5) 0.0525(15) Uani 1 1 d . . . . .
C2 C 0.5950(3) 0.6988(3) 0.8161(6) 0.0638(18) Uani 1 1 d . . . . .
H2 H 0.6298 0.7334 0.8280 0.077 Uiso 1 1 calc R U . . .
C3 C 0.5456(4) 0.7010(3) 0.7934(6) 0.077(2) Uani 1 1 d . . . . .
H3 H 0.5476 0.7371 0.7908 0.093 Uiso 1 1 calc R U . . .
C4 C 0.4929(3) 0.6511(4) 0.7743(6) 0.082(2) Uani 1 1 d . . . . .
H4 H 0.4600 0.6534 0.7567 0.099 Uiso 1 1 calc R U . . .
C5 C 0.4902(3) 0.5986(3) 0.7819(6) 0.070(2) Uani 1 1 d . . . . .
H5 H 0.4549 0.5646 0.7701 0.084 Uiso 1 1 calc R U . . .
C6 C 0.5392(3) 0.5950(3) 0.8069(5) 0.0571(16) Uani 1 1 d . . . . .
C7 C 0.5986(3) 0.5389(3) 0.7933(5) 0.0554(15) Uani 1 1 d . . . . .
C8 C 0.6482(3) 0.5933(3) 0.8068(4) 0.0515(16) Uani 1 1 d . . . . .
C9 C 0.7019(3) 0.5978(3) 0.7851(6) 0.0648(18) Uani 1 1 d . . . . .
H9 H 0.7360 0.6333 0.7944 0.078 Uiso 1 1 calc R U . . .
C10 C 0.7048(3) 0.5501(4) 0.7499(6) 0.074(2) Uani 1 1 d . . . . .
H10 H 0.7411 0.5539 0.7369 0.089 Uiso 1 1 calc R U . . .
C11 C 0.6556(4) 0.4970(3) 0.7335(7) 0.080(2) Uani 1 1 d . . . . .
H11 H 0.6583 0.4656 0.7075 0.095 Uiso 1 1 calc R U . . .
C12 C 0.6025(3) 0.4913(3) 0.7561(6) 0.073(2) Uani 1 1 d . . . . .
H12 H 0.5687 0.4555 0.7465 0.088 Uiso 1 1 calc R U . . .
C13 C 0.6981(3) 0.6955(3) 0.8692(5) 0.0624(18) Uani 1 1 d . . . . .
H13A H 0.7229 0.6843 0.9075 0.075 Uiso 1 1 calc R U . . .
H13B H 0.6880 0.7174 0.9185 0.075 Uiso 1 1 calc R U . . .
C14 C 0.7331(3) 0.7356(3) 0.7768(5) 0.0633(18) Uani 1 1 d . . . . .
H14A H 0.7442 0.7146 0.7274 0.076 Uiso 1 1 calc R U . . .
H14B H 0.7090 0.7476 0.7382 0.076 Uiso 1 1 calc R U . . .
C15 C 0.7867(3) 0.7885(3) 0.8171(7) 0.086(2) Uani 1 1 d . . . . .
H15A H 0.8072 0.7762 0.8655 0.104 Uiso 1 1 calc R U . . .
H15B H 0.7751 0.8123 0.8577 0.104 Uiso 1 1 calc R U . . .
C16 C 0.8279(3) 0.8252(3) 0.7297(8) 0.090(3) Uani 1 1 d . . . . .
H16A H 0.8068 0.8354 0.6786 0.107 Uiso 1 1 calc R U . . .
H16B H 0.8416 0.8023 0.6921 0.107 Uiso 1 1 calc R U . . .
C17 C 0.8801(5) 0.8806(5) 0.7704(12) 0.164(5) Uani 1 1 d . U . . .
H17A H 0.8670 0.9050 0.8044 0.197 Uiso 1 1 calc R U . . .
H17B H 0.9006 0.8710 0.8236 0.197 Uiso 1 1 calc R U . . .
C18 C 0.9201(6) 0.9130(6) 0.6807(15) 0.211(7) Uani 1 1 d . U . . .
H18A H 0.9426 0.8949 0.6623 0.316 Uiso 1 1 calc R U . . .
H18B H 0.9459 0.9527 0.7021 0.316 Uiso 1 1 calc R U . . .
H18C H 0.8978 0.9125 0.6196 0.316 Uiso 1 1 calc R U . . .
N1 N 0.64448(19) 0.6424(2) 0.8378(4) 0.0517(12) Uani 1 1 d . . . . .
O1 O 0.5267(2) 0.51843(18) 0.9492(4) 0.0732(13) Uani 1 1 d . . . . .
O2 O 0.4857(2) 0.4833(2) 0.7712(4) 0.0846(15) Uani 1 1 d . . . . .
S1 S 0.53131(7) 0.52740(7) 0.83514(15) 0.0601(5) 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
C1 N1 1.385(8) . ?
C1 C2 1.399(9) . ?
C1 C6 1.420(8) . ?
C2 C3 1.366(10) . ?
C2 H2 0.9300 . ?
C3 C4 1.381(11) . ?
C3 H3 0.9300 . ?
C4 C5 1.359(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(9) . ?
C5 H5 0.9300 . ?
C6 S1 1.731(7) . ?
C7 C8 1.391(8) . ?
C7 C12 1.394(9) . ?
C7 S1 1.731(6) . ?
C8 C9 1.393(8) . ?
C8 N1 1.406(8) . ?
C9 C10 1.375(9) . ?
C9 H9 0.9300 . ?
C10 C11 1.372(10) . ?
C10 H10 0.9300 . ?
C11 C12 1.367(10) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 N1 1.466(7) . ?
C13 C14 1.526(8) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.497(9) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.504(11) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.514(13) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.485(17) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
O1 S1 1.438(5) . ?
O2 S1 1.431(5) . ?

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
N1 C1 C2 122.8(5) . . ?
N1 C1 C6 121.5(6) . . ?
C2 C1 C6 115.6(6) . . ?
C3 C2 C1 121.5(7) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C2 C3 C4 121.8(7) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 118.5(7) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C4 C5 C6 121.0(7) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 121.4(7) . . ?
C5 C6 S1 119.0(5) . . ?
C1 C6 S1 119.1(5) . . ?
C8 C7 C12 121.2(6) . . ?
C8 C7 S1 120.1(5) . . ?
C12 C7 S1 118.4(5) . . ?
C7 C8 C9 117.3(6) . . ?
C7 C8 N1 121.7(6) . . ?
C9 C8 N1 121.0(6) . . ?
C10 C9 C8 120.5(7) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C9 121.9(7) . . ?
C11 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
C12 C11 C10 118.6(7) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
C11 C12 C7 120.4(7) . . ?
C11 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?
N1 C13 C14 115.1(5) . . ?
N1 C13 H13A 108.5 . . ?
C14 C13 H13A 108.5 . . ?
N1 C13 H13B 108.5 . . ?
C14 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?
C15 C14 C13 111.0(6) . . ?
C15 C14 H14A 109.4 . . ?
C13 C14 H14A 109.4 . . ?
C15 C14 H14B 109.4 . . ?
C13 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C14 C15 C16 113.8(7) . . ?
C14 C15 H15A 108.8 . . ?
C16 C15 H15A 108.8 . . ?
C14 C15 H15B 108.8 . . ?
C16 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C15 C16 C17 113.5(8) . . ?
C15 C16 H16A 108.9 . . ?
C17 C16 H16A 108.9 . . ?
C15 C16 H16B 108.9 . . ?
C17 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C18 C17 C16 110.4(12) . . ?
C18 C17 H17A 109.6 . . ?
C16 C17 H17A 109.6 . . ?
C18 C17 H17B 109.6 . . ?
C16 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C1 N1 C8 122.1(4) . . ?
C1 N1 C13 118.4(5) . . ?
C8 N1 C13 118.5(5) . . ?
O2 S1 O1 116.8(3) . . ?
O2 S1 C7 110.5(3) . . ?
O1 S1 C7 108.8(3) . . ?
O2 S1 C6 110.2(3) . . ?
O1 S1 C6 109.2(3) . . ?
C7 S1 C6 100.1(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 C3 175.6(6) . . . . ?
C6 C1 C2 C3 -2.3(9) . . . . ?
C1 C2 C3 C4 -0.5(11) . . . . ?
C2 C3 C4 C5 2.1(11) . . . . ?
C3 C4 C5 C6 -0.7(11) . . . . ?
C4 C5 C6 C1 -2.2(10) . . . . ?
C4 C5 C6 S1 170.4(6) . . . . ?
N1 C1 C6 C5 -174.3(6) . . . . ?
C2 C1 C6 C5 3.7(9) . . . . ?
N1 C1 C6 S1 13.0(8) . . . . ?
C2 C1 C6 S1 -169.0(5) . . . . ?
C12 C7 C8 C9 -2.1(9) . . . . ?
S1 C7 C8 C9 171.6(4) . . . . ?
C12 C7 C8 N1 175.9(6) . . . . ?
S1 C7 C8 N1 -10.5(8) . . . . ?
C7 C8 C9 C10 1.1(9) . . . . ?
N1 C8 C9 C10 -176.9(6) . . . . ?
C8 C9 C10 C11 1.0(10) . . . . ?
C9 C10 C11 C12 -2.1(11) . . . . ?
C10 C11 C12 C7 1.0(12) . . . . ?
C8 C7 C12 C11 1.0(11) . . . . ?
S1 C7 C12 C11 -172.7(6) . . . . ?
N1 C13 C14 C15 179.8(6) . . . . ?
C13 C14 C15 C16 171.0(7) . . . . ?
C14 C15 C16 C17 176.2(9) . . . . ?
C15 C16 C17 C18 177.2(10) . . . . ?
C2 C1 N1 C8 -157.0(6) . . . . ?
C6 C1 N1 C8 20.8(9) . . . . ?
C2 C1 N1 C13 11.5(9) . . . . ?
C6 C1 N1 C13 -170.7(5) . . . . ?
C7 C8 N1 C1 -22.3(8) . . . . ?
C9 C8 N1 C1 155.5(6) . . . . ?
C7 C8 N1 C13 169.1(6) . . . . ?
C9 C8 N1 C13 -13.0(8) . . . . ?
C14 C13 N1 C1 -83.7(8) . . . . ?
C14 C13 N1 C8 85.3(7) . . . . ?
C8 C7 S1 O2 151.3(5) . . . . ?
C12 C7 S1 O2 -34.9(6) . . . . ?
C8 C7 S1 O1 -79.3(6) . . . . ?
C12 C7 S1 O1 94.5(6) . . . . ?
C8 C7 S1 C6 35.1(6) . . . . ?
C12 C7 S1 C6 -151.1(6) . . . . ?
C5 C6 S1 O2 34.6(6) . . . . ?
C1 C6 S1 O2 -152.6(5) . . . . ?
C5 C6 S1 O1 -94.9(6) . . . . ?
C1 C6 S1 O1 77.9(5) . . . . ?
C5 C6 S1 C7 151.0(5) . . . . ?
C1 C6 S1 C7 -36.2(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
C9 H9 O2 0.93 2.62 3.310(8) 131.8 18_554
C9 H9 O2 0.93 2.62 3.310(8) 131.8 18_554
C9 H9 O2 0.93 2.62 3.310(8) 131.8 18_554

_refine_diff_density_max         0.311
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.040



####################################################################### 
# 
# 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_whu-3
_database_code_depnum_ccdc_archive 'CCDC 1879166'
loop_
_audit_author_name
_audit_author_address
'Yang Jie'
;Wuhan University
China
;
_audit_update_record             
;
2018-11-15 deposited with the CCDC.	2019-04-02 downloaded from the CCDC.
;
_audit_creation_date             2016-10-10
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_shelxl_version_number           2014-1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C15 H15 N O2 S'
_chemical_formula_sum            'C15 H15 N O2 S'
_chemical_formula_weight         273.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N S'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   7.7584(7)
_cell_length_b                   9.0839(8)
_cell_length_c                   10.0043(9)
_cell_angle_alpha                109.128(8)
_cell_angle_beta                 97.408(8)
_cell_angle_gamma                103.752(8)
_cell_volume                     630.39(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1270
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.9330
_cell_measurement_theta_min      4.7960
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.256
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93010
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'translucent light colourless'
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_unetI/netI     0.0664
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4603
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.055
_diffrn_reflns_theta_min         4.802
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3376
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -122.00   -1.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5605  -19.0000 -180.0000 121

#__ type_ start__ end____ width___ exp.time_
  2 omega  -49.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5605   37.0000    0.0000 82

#__ type_ start__ end____ width___ exp.time_
  3 omega  -49.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5605   37.0000 -180.0000 82

#__ type_ start__ end____ width___ exp.time_
  4 omega   23.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.5605 -125.0000   90.0000 75

#__ type_ start__ end____ width___ exp.time_
  5 omega   23.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.5605 -125.0000   30.0000 75

#__ type_ start__ end____ width___ exp.time_
  6 omega   23.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.5605 -125.0000 -180.0000 75

#__ type_ start__ end____ width___ exp.time_
  7 omega   94.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8759  125.0000  120.0000 84

#__ type_ start__ end____ width___ exp.time_
  8 omega   35.00  121.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8759 -125.0000 -150.0000 86

#__ type_ start__ end____ width___ exp.time_
  9 omega   39.00   91.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8759  -45.0000 -120.0000 52

#__ type_ start__ end____ width___ exp.time_
 10 omega   43.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8759  -30.0000    0.0000 47

#__ type_ start__ end____ width___ exp.time_
 11 omega   25.00   91.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8759  -94.0000   60.0000 66

#__ type_ start__ end____ width___ exp.time_
 12 omega   64.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8759  -30.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega   45.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8759  -94.0000 -120.0000 64

#__ type_ start__ end____ width___ exp.time_
 14 omega   83.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8759   30.0000  -60.0000 95

#__ type_ start__ end____ width___ exp.time_
 15 omega   31.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8759  -30.0000  120.0000 59

#__ type_ start__ end____ width___ exp.time_
 16 omega   30.00   68.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8759  -30.0000 -180.0000 38

#__ type_ start__ end____ width___ exp.time_
 17 omega  121.00  158.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8759   61.0000 -180.0000 37

#__ type_ start__ end____ width___ exp.time_
 18 omega  141.00  173.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8759  125.0000  -60.0000 32

#__ type_ start__ end____ width___ exp.time_
 19 omega  111.00  173.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8759  125.0000 -120.0000 62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1855105000
_diffrn_orient_matrix_UB_12      -0.0261492000
_diffrn_orient_matrix_UB_13      -0.0199576000
_diffrn_orient_matrix_UB_21      0.0658183000
_diffrn_orient_matrix_UB_22      0.0571532000
_diffrn_orient_matrix_UB_23      0.1658194000
_diffrn_orient_matrix_UB_31      -0.0726686000
_diffrn_orient_matrix_UB_32      -0.1772873000
_diffrn_orient_matrix_UB_33      -0.0096309000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1732
_reflns_number_total             2249
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2249
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0432
_refine_ls_restrained_S_all      1.040
_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)+(0.0340P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.0965
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C13(H13), C15(H15), C17(H17), C19(H19), C23(H23), C25(H25), C28(H28)
2.c Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
S1 S 0.79060(8) 0.64234(7) 0.30600(7) 0.01709(17) Uani 1 1 d . . . . .
O1 O 0.6621(2) 0.5915(2) 0.1692(2) 0.0209(4) Uani 1 1 d . . . . .
O4 O 0.7600(3) 0.7612(2) 0.4303(2) 0.0238(4) Uani 1 1 d . . . . .
N2 N 1.0169(3) 0.4254(2) 0.1821(2) 0.0154(4) Uani 1 1 d . . . . .
C1 C 1.0082(3) 0.7091(3) 0.2795(3) 0.0155(5) Uani 1 1 d . . . . .
C4 C 0.8032(3) 0.4697(3) 0.3405(3) 0.0161(5) Uani 1 1 d . . . . .
C6 C 1.0886(3) 0.5913(3) 0.2070(3) 0.0147(5) Uani 1 1 d . . . . .
C8 C 0.8997(3) 0.3711(3) 0.2625(3) 0.0154(5) Uani 1 1 d . . . . .
C10 C 1.2719(3) 0.2977(3) 0.1765(3) 0.0175(5) Uani 1 1 d . . . . .
H10A H 1.3592 0.4056 0.2244 0.021 Uiso 1 1 calc R . . . .
H10B H 1.2416 0.2553 0.2506 0.021 Uiso 1 1 calc R . . . .
C11 C 1.2513(4) 0.9300(3) 0.2834(3) 0.0195(5) Uani 1 1 d . . . . .
H11 H 1.3094 1.0412 0.3127 0.023 Uiso 1 1 calc R . . . .
C13 C 0.7667(3) 0.1692(3) 0.3602(3) 0.0203(6) Uani 1 1 d . . . . .
H13 H 0.7506 0.0658 0.3634 0.024 Uiso 1 1 calc R . . . .
C15 C 1.0891(3) 0.8757(3) 0.3194(3) 0.0180(5) Uani 1 1 d . . . . .
H15 H 1.0340 0.9501 0.3700 0.022 Uiso 1 1 calc R . . . .
C17 C 1.2498(3) 0.6502(3) 0.1651(3) 0.0179(5) Uani 1 1 d . . . . .
H17 H 1.3044 0.5770 0.1119 0.022 Uiso 1 1 calc R . . . .
C19 C 1.3271(4) 0.8160(3) 0.2027(3) 0.0199(6) Uani 1 1 d . . . . .
H19 H 1.4327 0.8524 0.1732 0.024 Uiso 1 1 calc R . . . .
C21 C 1.1002(3) 0.3099(3) 0.0927(3) 0.0155(5) Uani 1 1 d . . . . .
H21A H 1.1303 0.3433 0.0138 0.019 Uiso 1 1 calc R . . . .
H21B H 1.0113 0.2025 0.0503 0.019 Uiso 1 1 calc R . . . .
C23 C 0.6990(3) 0.4226(3) 0.4322(3) 0.0192(5) Uani 1 1 d . . . . .
H23 H 0.6426 0.4933 0.4865 0.023 Uiso 1 1 calc R . . . .
C25 C 0.6797(4) 0.2727(3) 0.4422(3) 0.0223(6) Uani 1 1 d . . . . .
H25 H 0.6101 0.2406 0.5024 0.027 Uiso 1 1 calc R . . . .
C28 C 0.8762(3) 0.2173(3) 0.2745(3) 0.0195(5) Uani 1 1 d . . . . .
H28 H 0.9355 0.1471 0.2236 0.023 Uiso 1 1 calc R . . . .
C30 C 1.3565(4) 0.1859(3) 0.0743(3) 0.0237(6) Uani 1 1 d . . . . .
H30A H 1.3840 0.2266 -0.0002 0.036 Uiso 1 1 calc GR . . . .
H30B H 1.2722 0.0778 0.0306 0.036 Uiso 1 1 calc GR . . . .
H30C H 1.4665 0.1826 0.1279 0.036 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4478(19) . ?
S1 O4 1.4447(17) . ?
S1 C1 1.739(2) . ?
S1 C4 1.735(2) . ?
N2 C6 1.400(3) . ?
N2 C8 1.398(3) . ?
N2 C21 1.475(3) . ?
C1 C6 1.408(3) . ?
C1 C15 1.390(3) . ?
C4 C8 1.408(3) . ?
C4 C23 1.400(3) . ?
C6 C17 1.411(3) . ?
C8 C28 1.412(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C21 1.528(3) . ?
C10 C30 1.522(3) . ?
C11 H11 0.9300 . ?
C11 C15 1.376(3) . ?
C11 C19 1.390(4) . ?
C13 H13 0.9300 . ?
C13 C25 1.397(4) . ?
C13 C28 1.380(3) . ?
C15 H15 0.9300 . ?
C17 H17 0.9300 . ?
C17 C19 1.383(3) . ?
C19 H19 0.9300 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C23 H23 0.9300 . ?
C23 C25 1.372(4) . ?
C25 H25 0.9300 . ?
C28 H28 0.9300 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 C1 107.93(11) . . ?
O1 S1 C4 108.50(11) . . ?
O4 S1 O1 116.84(11) . . ?
O4 S1 C1 111.20(11) . . ?
O4 S1 C4 110.76(12) . . ?
C4 S1 C1 100.30(12) . . ?
C6 N2 C21 117.93(19) . . ?
C8 N2 C6 122.2(2) . . ?
C8 N2 C21 118.36(19) . . ?
C6 C1 S1 118.43(18) . . ?
C15 C1 S1 118.69(18) . . ?
C15 C1 C6 122.6(2) . . ?
C8 C4 S1 119.01(18) . . ?
C23 C4 S1 118.54(19) . . ?
C23 C4 C8 122.0(2) . . ?
N2 C6 C1 122.2(2) . . ?
N2 C6 C17 121.4(2) . . ?
C1 C6 C17 116.3(2) . . ?
N2 C8 C4 121.6(2) . . ?
N2 C8 C28 122.2(2) . . ?
C4 C8 C28 116.2(2) . . ?
H10A C10 H10B 108.1 . . ?
C21 C10 H10A 109.6 . . ?
C21 C10 H10B 109.5 . . ?
C30 C10 H10A 109.5 . . ?
C30 C10 H10B 109.5 . . ?
C30 C10 C21 110.5(2) . . ?
C15 C11 H11 120.5 . . ?
C15 C11 C19 119.0(2) . . ?
C19 C11 H11 120.5 . . ?
C25 C13 H13 119.3 . . ?
C28 C13 H13 119.3 . . ?
C28 C13 C25 121.3(2) . . ?
C1 C15 H15 120.2 . . ?
C11 C15 C1 119.6(2) . . ?
C11 C15 H15 120.2 . . ?
C6 C17 H17 119.8 . . ?
C19 C17 C6 120.4(2) . . ?
C19 C17 H17 119.8 . . ?
C11 C19 H19 119.1 . . ?
C17 C19 C11 121.8(2) . . ?
C17 C19 H19 119.1 . . ?
N2 C21 C10 114.0(2) . . ?
N2 C21 H21A 108.7 . . ?
N2 C21 H21B 108.7 . . ?
C10 C21 H21A 108.7 . . ?
C10 C21 H21B 108.7 . . ?
H21A C21 H21B 107.6 . . ?
C4 C23 H23 119.9 . . ?
C25 C23 C4 120.3(2) . . ?
C25 C23 H23 119.9 . . ?
C13 C25 H25 120.6 . . ?
C23 C25 C13 118.8(2) . . ?
C23 C25 H25 120.6 . . ?
C8 C28 H28 119.4 . . ?
C13 C28 C8 121.3(2) . . ?
C13 C28 H28 119.4 . . ?
C10 C30 H30A 109.5 . . ?
C10 C30 H30B 109.5 . . ?
C10 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 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
S1 C1 C6 N2 -13.1(3) . . . . ?
S1 C1 C6 C17 169.08(18) . . . . ?
S1 C1 C15 C11 -172.2(2) . . . . ?
S1 C4 C8 N2 13.9(3) . . . . ?
S1 C4 C8 C28 -168.21(18) . . . . ?
S1 C4 C23 C25 168.5(2) . . . . ?
O1 S1 C1 C6 -76.3(2) . . . . ?
O1 S1 C1 C15 98.4(2) . . . . ?
O1 S1 C4 C8 75.2(2) . . . . ?
O1 S1 C4 C23 -97.2(2) . . . . ?
O4 S1 C1 C6 154.37(19) . . . . ?
O4 S1 C1 C15 -31.0(2) . . . . ?
O4 S1 C4 C8 -155.28(19) . . . . ?
O4 S1 C4 C23 32.3(2) . . . . ?
N2 C6 C17 C19 -174.0(2) . . . . ?
N2 C8 C28 C13 176.8(2) . . . . ?
C1 S1 C4 C8 -37.8(2) . . . . ?
C1 S1 C4 C23 149.8(2) . . . . ?
C1 C6 C17 C19 3.8(4) . . . . ?
C4 S1 C1 C6 37.2(2) . . . . ?
C4 S1 C1 C15 -148.2(2) . . . . ?
C4 C8 C28 C13 -1.1(4) . . . . ?
C4 C23 C25 C13 0.4(4) . . . . ?
C6 N2 C8 C4 19.8(4) . . . . ?
C6 N2 C8 C28 -158.0(2) . . . . ?
C6 N2 C21 C10 82.6(3) . . . . ?
C6 C1 C15 C11 2.2(4) . . . . ?
C6 C17 C19 C11 0.7(4) . . . . ?
C8 N2 C6 C1 -20.2(4) . . . . ?
C8 N2 C6 C17 157.5(2) . . . . ?
C8 N2 C21 C10 -83.7(3) . . . . ?
C8 C4 C23 C25 -3.7(4) . . . . ?
C15 C1 C6 N2 172.5(2) . . . . ?
C15 C1 C6 C17 -5.3(4) . . . . ?
C15 C11 C19 C17 -4.0(4) . . . . ?
C19 C11 C15 C1 2.5(4) . . . . ?
C21 N2 C6 C1 174.1(2) . . . . ?
C21 N2 C6 C17 -8.2(3) . . . . ?
C21 N2 C8 C4 -174.5(2) . . . . ?
C21 N2 C8 C28 7.7(3) . . . . ?
C23 C4 C8 N2 -173.9(2) . . . . ?
C23 C4 C8 C28 4.0(4) . . . . ?
C25 C13 C28 C8 -2.1(4) . . . . ?
C28 C13 C25 C23 2.5(4) . . . . ?
C30 C10 C21 N2 -175.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
