# Electronic Supplementary Material (ESI) for Organic 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. 
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data_190127cyh_0m
_database_code_depnum_ccdc_archive 'CCDC 1911410'
loop_
_audit_author_name
_audit_author_address
'Yankai Liu'
;Ocean University of China
China
;
_audit_update_record             
;
2019-04-22 deposited with the CCDC.	2019-10-02 downloaded from the CCDC.
;
_audit_creation_date             2019-01-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H23 N O3 S'
_chemical_formula_sum            'C25 H23 N O3 S'
_chemical_formula_weight         417.50
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.1372(11)
_cell_length_b                   8.2426(8)
_cell_length_c                   12.2345(12)
_cell_angle_alpha                90
_cell_angle_beta                 110.1870(10)
_cell_angle_gamma                90
_cell_volume                     1054.13(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2758
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.882
_cell_measurement_theta_min      3.042
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7039
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/3 (Bruker,2014/3) was used for absorption correction. wR2(int) was 0.0397 before and 0.0324 after correction. The Ratio of minimum to maximum transmission is 0.9441. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0163
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6418
_diffrn_reflns_point_group_measured_fraction_full 0.904
_diffrn_reflns_point_group_measured_fraction_max 0.857
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.539
_diffrn_reflns_theta_min         3.042
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.632
_reflns_Friedel_fraction_full    0.797
_reflns_Friedel_fraction_max     0.713
_reflns_number_gt                3592
_reflns_number_total             4163
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 1264 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_coef       0.043(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         4163
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0336
_refine_ls_restrained_S_all      1.048
_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)+(0.0464P)²+0.0348P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0807
_refine_ls_wR_factor_ref         0.0860
_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 Ternary CH refined with riding coordinates:
 C1(H1), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C15(H15), C16(H16), C17(H17),
 C18(H18), C20(H20), C21(H21), C23(H23), C24(H24)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.33274(6) 0.32663(9) 0.77273(5) 0.04503(19) Uani 1 1 d . . . . .
O1 O 0.29078(18) 0.4522(3) 0.83182(17) 0.0589(6) Uani 1 1 d . . . . .
O2 O 0.3225(2) 0.1613(3) 0.80546(18) 0.0632(6) Uani 1 1 d . . . . .
O3 O 0.66792(17) 0.1961(2) 0.80998(16) 0.0517(5) Uani 1 1 d . . . . .
N1 N 0.48607(18) 0.3566(3) 0.78772(16) 0.0404(5) Uani 1 1 d . . . . .
C1 C 0.5795(2) 0.2426(4) 0.8653(2) 0.0490(7) Uani 1 1 d . . . . .
H1 H 0.533746 0.145793 0.876113 0.059 Uiso 1 1 calc R . . . .
C2 C 0.7862(2) 0.2712(3) 0.8419(2) 0.0424(6) Uani 1 1 d . . . . .
C3 C 0.8188(2) 0.4017(4) 0.9172(2) 0.0450(6) Uani 1 1 d . . . . .
C4 C 0.7184(2) 0.4656(4) 0.9631(2) 0.0497(7) Uani 1 1 d . . . . .
H4 H 0.758849 0.523809 1.036505 0.060 Uiso 1 1 calc R . . . .
C5 C 0.6441(3) 0.3210(5) 0.9823(2) 0.0582(8) Uani 1 1 d . . . . .
H5A H 0.701421 0.244596 1.035472 0.070 Uiso 1 1 calc R . . . .
H5B H 0.580788 0.355907 1.015453 0.070 Uiso 1 1 calc R . . . .
C6 C 0.6324(2) 0.5786(3) 0.8723(2) 0.0430(6) Uani 1 1 d . . . . .
C7 C 0.5253(2) 0.5247(3) 0.7911(2) 0.0374(5) Uani 1 1 d . . . . .
C8 C 0.4473(2) 0.6232(3) 0.6901(2) 0.0358(5) Uani 1 1 d . . . . .
C9 C 0.4516(2) 0.5891(3) 0.5802(2) 0.0430(6) Uani 1 1 d . . . . .
H9 H 0.502679 0.504959 0.570659 0.052 Uiso 1 1 calc R . . . .
C10 C 0.3799(3) 0.6801(4) 0.4850(2) 0.0540(7) Uani 1 1 d . . . . .
H10 H 0.382919 0.656527 0.411657 0.065 Uiso 1 1 calc R . . . .
C11 C 0.3046(3) 0.8047(4) 0.4981(2) 0.0575(8) Uani 1 1 d . . . . .
H11 H 0.256295 0.865069 0.433698 0.069 Uiso 1 1 calc R . . . .
C12 C 0.3004(3) 0.8404(4) 0.6065(2) 0.0564(7) Uani 1 1 d . . . . .
H12 H 0.249341 0.924961 0.615526 0.068 Uiso 1 1 calc R . . . .
C13 C 0.3722(2) 0.7505(3) 0.7018(2) 0.0466(6) Uani 1 1 d . . . . .
H13 H 0.369918 0.776121 0.775089 0.056 Uiso 1 1 calc R . . . .
C14 C 0.6815(3) 0.7475(4) 0.8704(3) 0.0598(8) Uani 1 1 d . . . . .
H14A H 0.631626 0.800050 0.799164 0.090 Uiso 1 1 calc GR . . . .
H14B H 0.769385 0.743216 0.875594 0.090 Uiso 1 1 calc GR . . . .
H14C H 0.674749 0.807521 0.935332 0.090 Uiso 1 1 calc GR . . . .
C15 C 0.9398(3) 0.4696(4) 0.9422(3) 0.0587(8) Uani 1 1 d . . . . .
H15 H 0.964144 0.556156 0.993907 0.070 Uiso 1 1 calc R . . . .
C16 C 1.0243(3) 0.4110(5) 0.8918(3) 0.0650(9) Uani 1 1 d . . . . .
H16 H 1.104316 0.458692 0.908433 0.078 Uiso 1 1 calc R . . . .
C17 C 0.9893(3) 0.2817(4) 0.8168(3) 0.0626(9) Uani 1 1 d . . . . .
H17 H 1.045837 0.242211 0.782230 0.075 Uiso 1 1 calc R . . . .
C18 C 0.8710(3) 0.2098(4) 0.7921(2) 0.0550(8) Uani 1 1 d . . . . .
H18 H 0.848486 0.120762 0.742465 0.066 Uiso 1 1 calc R . . . .
C19 C 0.2441(2) 0.3424(4) 0.6221(2) 0.0417(6) Uani 1 1 d . . . . .
C20 C 0.2745(3) 0.2474(4) 0.5428(2) 0.0530(7) Uani 1 1 d . . . . .
H20 H 0.348678 0.185140 0.566169 0.064 Uiso 1 1 calc R . . . .
C21 C 0.1936(3) 0.2456(4) 0.4279(2) 0.0621(8) Uani 1 1 d . . . . .
H21 H 0.214117 0.181277 0.374470 0.075 Uiso 1 1 calc R . . . .
C22 C 0.0827(3) 0.3374(4) 0.3906(2) 0.0581(7) Uani 1 1 d . . . . .
C23 C 0.0577(3) 0.4356(4) 0.4713(3) 0.0620(8) Uani 1 1 d . . . . .
H23 H -0.014459 0.501630 0.447474 0.074 Uiso 1 1 calc R . . . .
C24 C 0.1366(3) 0.4389(4) 0.5865(3) 0.0558(7) Uani 1 1 d . . . . .
H24 H 0.117397 0.505587 0.639539 0.067 Uiso 1 1 calc R . . . .
C25 C -0.0080(4) 0.3286(6) 0.2663(3) 0.0818(11) Uani 1 1 d . . . . .
H25A H 0.039428 0.339161 0.214386 0.123 Uiso 1 1 calc GR . . . .
H25B H -0.069371 0.414826 0.252174 0.123 Uiso 1 1 calc GR . . . .
H25C H -0.051600 0.226087 0.253367 0.123 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 1.430(2) . ?
S1 O2 1.436(2) . ?
S1 N1 1.672(2) . ?
S1 C19 1.769(2) . ?
O3 C1 1.427(3) . ?
O3 C2 1.384(3) . ?
N1 C1 1.478(3) . ?
N1 C7 1.449(3) . ?
C1 H1 0.9800 . ?
C1 C5 1.508(4) . ?
C2 C3 1.381(4) . ?
C2 C18 1.385(4) . ?
C3 C4 1.508(4) . ?
C3 C15 1.393(4) . ?
C4 H4 0.9800 . ?
C4 C5 1.515(5) . ?
C4 C6 1.511(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.337(3) . ?
C6 C14 1.499(4) . ?
C7 C8 1.484(3) . ?
C8 C9 1.390(3) . ?
C8 C13 1.380(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.383(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.370(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.374(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.380(4) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15 0.9300 . ?
C15 C16 1.378(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.372(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.380(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.377(4) . ?
C19 C24 1.377(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.383(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.384(5) . ?
C22 C23 1.377(4) . ?
C22 C25 1.509(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.380(4) . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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 118.33(13) . . ?
O1 S1 N1 109.71(11) . . ?
O1 S1 C19 108.12(13) . . ?
O2 S1 N1 106.62(12) . . ?
O2 S1 C19 106.88(13) . . ?
N1 S1 C19 106.58(10) . . ?
C2 O3 C1 119.4(2) . . ?
C1 N1 S1 116.27(17) . . ?
C7 N1 S1 115.54(16) . . ?
C7 N1 C1 116.8(2) . . ?
O3 C1 N1 108.31(19) . . ?
O3 C1 H1 108.7 . . ?
O3 C1 C5 112.6(2) . . ?
N1 C1 H1 108.7 . . ?
N1 C1 C5 109.7(3) . . ?
C5 C1 H1 108.7 . . ?
O3 C2 C18 116.1(3) . . ?
C3 C2 O3 122.8(2) . . ?
C3 C2 C18 121.1(3) . . ?
C2 C3 C4 117.5(3) . . ?
C2 C3 C15 118.1(3) . . ?
C15 C3 C4 124.3(3) . . ?
C3 C4 H4 110.3 . . ?
C3 C4 C5 107.3(3) . . ?
C3 C4 C6 107.7(2) . . ?
C5 C4 H4 110.3 . . ?
C6 C4 H4 110.3 . . ?
C6 C4 C5 110.9(2) . . ?
C1 C5 C4 107.3(2) . . ?
C1 C5 H5A 110.3 . . ?
C1 C5 H5B 110.3 . . ?
C4 C5 H5A 110.3 . . ?
C4 C5 H5B 110.3 . . ?
H5A C5 H5B 108.5 . . ?
C7 C6 C4 121.2(3) . . ?
C7 C6 C14 122.2(2) . . ?
C14 C6 C4 116.2(2) . . ?
N1 C7 C8 114.5(2) . . ?
C6 C7 N1 121.5(2) . . ?
C6 C7 C8 123.6(2) . . ?
C9 C8 C7 119.3(2) . . ?
C13 C8 C7 122.1(2) . . ?
C13 C8 C9 118.6(2) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.1(3) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.4(3) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 119.9(3) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C13 119.8(3) . . ?
C13 C12 H12 120.1 . . ?
C8 C13 C12 121.0(2) . . ?
C8 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C6 C14 H14A 109.5 . . ?
C6 C14 H14B 109.5 . . ?
C6 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C3 C15 H15 119.3 . . ?
C16 C15 C3 121.3(3) . . ?
C16 C15 H15 119.3 . . ?
C15 C16 H16 120.3 . . ?
C17 C16 C15 119.4(3) . . ?
C17 C16 H16 120.3 . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.6(3) . . ?
C18 C17 H17 119.7 . . ?
C2 C18 H18 120.3 . . ?
C17 C18 C2 119.4(3) . . ?
C17 C18 H18 120.3 . . ?
C20 C19 S1 120.5(2) . . ?
C24 C19 S1 118.9(2) . . ?
C24 C19 C20 120.2(2) . . ?
C19 C20 H20 120.3 . . ?
C19 C20 C21 119.3(3) . . ?
C21 C20 H20 120.3 . . ?
C20 C21 H21 119.2 . . ?
C20 C21 C22 121.6(3) . . ?
C22 C21 H21 119.2 . . ?
C21 C22 C25 121.1(3) . . ?
C23 C22 C21 117.6(3) . . ?
C23 C22 C25 121.3(3) . . ?
C22 C23 H23 119.1 . . ?
C22 C23 C24 121.9(3) . . ?
C24 C23 H23 119.1 . . ?
C19 C24 C23 119.3(3) . . ?
C19 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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 N1 C1 O3 136.31(19) . . . . ?
S1 N1 C1 C5 -100.4(2) . . . . ?
S1 N1 C7 C6 132.6(2) . . . . ?
S1 N1 C7 C8 -54.9(2) . . . . ?
S1 C19 C20 C21 171.2(2) . . . . ?
S1 C19 C24 C23 -171.6(2) . . . . ?
O1 S1 N1 C1 108.4(2) . . . . ?
O1 S1 N1 C7 -34.1(2) . . . . ?
O1 S1 C19 C20 172.8(2) . . . . ?
O1 S1 C19 C24 -13.5(3) . . . . ?
O2 S1 N1 C1 -20.9(2) . . . . ?
O2 S1 N1 C7 -163.33(18) . . . . ?
O2 S1 C19 C20 -58.8(3) . . . . ?
O2 S1 C19 C24 114.9(2) . . . . ?
O3 C1 C5 C4 57.0(3) . . . . ?
O3 C2 C3 C4 -1.6(4) . . . . ?
O3 C2 C3 C15 -179.1(2) . . . . ?
O3 C2 C18 C17 177.9(2) . . . . ?
N1 S1 C19 C20 55.0(3) . . . . ?
N1 S1 C19 C24 -131.4(2) . . . . ?
N1 C1 C5 C4 -63.7(3) . . . . ?
N1 C7 C8 C9 -66.7(3) . . . . ?
N1 C7 C8 C13 114.6(3) . . . . ?
C1 O3 C2 C3 -6.7(3) . . . . ?
C1 O3 C2 C18 174.4(2) . . . . ?
C1 N1 C7 C6 -9.7(3) . . . . ?
C1 N1 C7 C8 162.9(2) . . . . ?
C2 O3 C1 N1 99.2(3) . . . . ?
C2 O3 C1 C5 -22.2(3) . . . . ?
C2 C3 C4 C5 36.7(3) . . . . ?
C2 C3 C4 C6 -82.8(3) . . . . ?
C2 C3 C15 C16 1.2(4) . . . . ?
C3 C2 C18 C17 -1.0(4) . . . . ?
C3 C4 C5 C1 -62.6(3) . . . . ?
C3 C4 C6 C7 92.5(3) . . . . ?
C3 C4 C6 C14 -80.8(3) . . . . ?
C3 C15 C16 C17 -1.0(5) . . . . ?
C4 C3 C15 C16 -176.1(3) . . . . ?
C4 C6 C7 N1 1.0(4) . . . . ?
C4 C6 C7 C8 -170.9(2) . . . . ?
C5 C4 C6 C7 -24.7(3) . . . . ?
C5 C4 C6 C14 162.0(2) . . . . ?
C6 C4 C5 C1 54.8(3) . . . . ?
C6 C7 C8 C9 105.6(3) . . . . ?
C6 C7 C8 C13 -73.0(3) . . . . ?
C7 N1 C1 O3 -81.7(3) . . . . ?
C7 N1 C1 C5 41.5(3) . . . . ?
C7 C8 C9 C10 -179.7(2) . . . . ?
C7 C8 C13 C12 -180.0(3) . . . . ?
C8 C9 C10 C11 0.2(4) . . . . ?
C9 C8 C13 C12 1.4(4) . . . . ?
C9 C10 C11 C12 0.3(4) . . . . ?
C10 C11 C12 C13 0.0(5) . . . . ?
C11 C12 C13 C8 -0.9(4) . . . . ?
C13 C8 C9 C10 -1.0(4) . . . . ?
C14 C6 C7 N1 173.9(2) . . . . ?
C14 C6 C7 C8 2.0(4) . . . . ?
C15 C3 C4 C5 -146.0(3) . . . . ?
C15 C3 C4 C6 94.5(3) . . . . ?
C15 C16 C17 C18 -0.4(5) . . . . ?
C16 C17 C18 C2 1.3(4) . . . . ?
C18 C2 C3 C4 177.3(2) . . . . ?
C18 C2 C3 C15 -0.2(4) . . . . ?
C19 S1 N1 C1 -134.8(2) . . . . ?
C19 S1 N1 C7 82.77(19) . . . . ?
C19 C20 C21 C22 0.1(5) . . . . ?
C20 C19 C24 C23 2.0(4) . . . . ?
C20 C21 C22 C23 2.3(5) . . . . ?
C20 C21 C22 C25 -177.2(3) . . . . ?
C21 C22 C23 C24 -2.6(5) . . . . ?
C22 C23 C24 C19 0.5(5) . . . . ?
C24 C19 C20 C21 -2.3(4) . . . . ?
C25 C22 C23 C24 176.8(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_181206cyh_0m
_database_code_depnum_ccdc_archive 'CCDC 1911412'
loop_
_audit_author_name
_audit_author_address
'Yankai Liu'
;Ocean University of China
China
;
_audit_update_record             
;
2019-04-22 deposited with the CCDC.	2019-10-02 downloaded from the CCDC.
;
_audit_creation_date             2018-12-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H25 N O4 S'
_chemical_formula_sum            'C25 H25 N O4 S'
_chemical_formula_weight         435.52
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   26.476(4)
_cell_length_b                   9.6581(15)
_cell_length_c                   9.1391(14)
_cell_angle_alpha                90
_cell_angle_beta                 98.974(3)
_cell_angle_gamma                90
_cell_volume                     2308.3(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2524
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      23.645
_cell_measurement_theta_min      2.935
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6340
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/3 (Bruker,2014/3) was used for absorption correction. wR2(int) was 0.0896 before and 0.0371 after correction. The Ratio of minimum to maximum transmission is 0.8503. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6883
_diffrn_reflns_point_group_measured_fraction_full 0.897
_diffrn_reflns_point_group_measured_fraction_max 0.848
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.491
_diffrn_reflns_theta_min         2.534
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.633
_reflns_Friedel_fraction_full    0.784
_reflns_Friedel_fraction_max     0.699
_reflns_number_gt                3509
_reflns_number_total             4503
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 1159 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         4503
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0416
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0386P)²+0.7359P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.0950
_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, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C12(H12), C15(H15), C16(H16), C17(H17), C18(H18),
 C20(H20), C21(H21), C23(H23), C24(H24)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.21906(3) 0.16538(8) 0.48223(9) 0.0439(2) Uani 1 1 d . . . . .
O1 O 0.19445(9) 0.0566(3) 0.5499(3) 0.0583(7) Uani 1 1 d . . . . .
O2 O 0.22467(10) 0.2988(2) 0.5515(3) 0.0566(7) Uani 1 1 d . . . . .
O3 O 0.29672(8) 0.1642(4) 0.2463(2) 0.0654(7) Uani 1 1 d . . . . .
O4 O 0.46144(10) 0.2832(3) 0.6442(3) 0.0612(7) Uani 1 1 d . . . . .
N1 N 0.27660(11) 0.1071(3) 0.4766(3) 0.0446(7) Uani 1 1 d . . . . .
H1 H 0.2754(15) 0.022(4) 0.454(4) 0.067 Uiso 1 1 d R . . . .
C1 C 0.31197(11) 0.1848(4) 0.4030(3) 0.0426(7) Uani 1 1 d . . . . .
H1A H 0.309651 0.283389 0.426529 0.051 Uiso 1 1 calc R . . . .
C2 C 0.33153(13) 0.1902(4) 0.1533(3) 0.0479(8) Uani 1 1 d . . . . .
C3 C 0.38332(12) 0.2074(3) 0.2039(3) 0.0434(8) Uani 1 1 d . . . . .
C4 C 0.40330(12) 0.2118(3) 0.3680(3) 0.0437(8) Uani 1 1 d . . . . .
H4 H 0.436104 0.162843 0.385456 0.052 Uiso 1 1 calc R . . . .
C5 C 0.41259(12) 0.3621(3) 0.4186(3) 0.0437(8) Uani 1 1 d . . . . .
H5A H 0.429931 0.409425 0.347099 0.052 Uiso 1 1 calc R . . . .
H5B H 0.379665 0.406615 0.416936 0.052 Uiso 1 1 calc R . . . .
C6 C 0.44346(11) 0.3824(4) 0.5705(3) 0.0443(8) Uani 1 1 d . . . . .
C7 C 0.45311(12) 0.5261(4) 0.6243(4) 0.0459(8) Uani 1 1 d . . . . .
C8 C 0.43302(13) 0.6410(4) 0.5447(4) 0.0589(10) Uani 1 1 d . . . . .
H8 H 0.411092 0.628097 0.455855 0.071 Uiso 1 1 calc R . . . .
C9 C 0.44471(17) 0.7736(4) 0.5939(5) 0.0743(13) Uani 1 1 d . . . . .
H9 H 0.430734 0.848231 0.537191 0.089 Uiso 1 1 calc R . . . .
C10 C 0.47635(19) 0.7979(5) 0.7239(5) 0.0759(13) Uani 1 1 d . . . . .
C11 C 0.49691(16) 0.6850(6) 0.8048(4) 0.0752(12) Uani 1 1 d . . . . .
H11 H 0.518920 0.699451 0.893244 0.090 Uiso 1 1 calc R . . . .
C12 C 0.48548(15) 0.5499(5) 0.7572(4) 0.0617(10) Uani 1 1 d . . . . .
H12 H 0.499488 0.475600 0.814294 0.074 Uiso 1 1 calc R . . . .
C13 C 0.4896(3) 0.9438(6) 0.7780(7) 0.128(2) Uani 1 1 d . . . . .
H13A H 0.488646 1.004621 0.694448 0.191 Uiso 1 1 calc GR . . . .
H13B H 0.523328 0.944700 0.834882 0.191 Uiso 1 1 calc GR . . . .
H13C H 0.465348 0.974536 0.838738 0.191 Uiso 1 1 calc GR . . . .
C14 C 0.36582(12) 0.1351(3) 0.4512(3) 0.0458(8) Uani 1 1 d . . . . .
H14A H 0.367650 0.036489 0.432395 0.055 Uiso 1 1 calc R . . . .
H14B H 0.375407 0.149978 0.556856 0.055 Uiso 1 1 calc R . . . .
C15 C 0.41533(15) 0.2250(4) 0.0972(4) 0.0571(9) Uani 1 1 d . . . . .
H15 H 0.450255 0.236880 0.127480 0.068 Uiso 1 1 calc R . . . .
C16 C 0.39612(19) 0.2252(4) -0.0517(4) 0.0669(11) Uani 1 1 d . . . . .
H16 H 0.418131 0.235376 -0.120940 0.080 Uiso 1 1 calc R . . . .
C17 C 0.34464(18) 0.2103(4) -0.0981(4) 0.0682(11) Uani 1 1 d . . . . .
H17 H 0.331680 0.212656 -0.198730 0.082 Uiso 1 1 calc R . . . .
C18 C 0.31215(16) 0.1918(4) 0.0038(4) 0.0615(10) Uani 1 1 d . . . . .
H18 H 0.277263 0.180408 -0.027719 0.074 Uiso 1 1 calc R . . . .
C19 C 0.18929(11) 0.1877(3) 0.2988(3) 0.0436(8) Uani 1 1 d . . . . .
C20 C 0.17387(18) 0.0748(4) 0.2141(5) 0.0722(13) Uani 1 1 d . . . . .
H20 H 0.175064 -0.012819 0.256817 0.087 Uiso 1 1 calc R . . . .
C21 C 0.1564(2) 0.0910(5) 0.0642(5) 0.0838(15) Uani 1 1 d . . . . .
H21 H 0.146777 0.012995 0.006881 0.101 Uiso 1 1 calc R . . . .
C22 C 0.15294(15) 0.2173(5) -0.0014(4) 0.0673(11) Uani 1 1 d . . . . .
C23 C 0.1665(2) 0.3302(5) 0.0873(5) 0.0915(16) Uani 1 1 d . . . . .
H23 H 0.163145 0.418417 0.046028 0.110 Uiso 1 1 calc R . . . .
C24 C 0.18484(19) 0.3159(4) 0.2356(5) 0.0764(14) Uani 1 1 d . . . . .
H24 H 0.194262 0.393861 0.293097 0.092 Uiso 1 1 calc R . . . .
C25 C 0.1368(2) 0.2353(7) -0.1671(5) 0.1047(18) Uani 1 1 d . . . . .
H25A H 0.158135 0.179094 -0.219079 0.157 Uiso 1 1 calc GR . . . .
H25B H 0.140333 0.330713 -0.193128 0.157 Uiso 1 1 calc GR . . . .
H25C H 0.101804 0.207348 -0.194046 0.157 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 1.427(2) . ?
S1 O2 1.433(2) . ?
S1 N1 1.632(3) . ?
S1 C19 1.751(3) . ?
O3 C1 1.440(3) . ?
O3 C2 1.370(4) . ?
O4 C6 1.224(4) . ?
N1 C1 1.445(4) . ?
C1 C14 1.504(4) . ?
C2 C3 1.387(4) . ?
C2 C18 1.383(4) . ?
C3 C4 1.511(4) . ?
C3 C15 1.398(4) . ?
C4 C5 1.531(5) . ?
C4 C14 1.532(4) . ?
C5 C6 1.510(4) . ?
C6 C7 1.482(5) . ?
C7 C8 1.386(5) . ?
C7 C12 1.392(5) . ?
C8 C9 1.377(6) . ?
C9 C10 1.363(6) . ?
C10 C11 1.381(7) . ?
C10 C13 1.517(6) . ?
C11 C12 1.393(6) . ?
C15 C16 1.377(5) . ?
C16 C17 1.370(6) . ?
C17 C18 1.375(5) . ?
C19 C20 1.363(5) . ?
C19 C24 1.363(5) . ?
C20 C21 1.385(6) . ?
C21 C22 1.357(6) . ?
C22 C23 1.372(6) . ?
C22 C25 1.518(6) . ?
C23 C24 1.374(6) . ?

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 119.55(15) . . ?
O1 S1 N1 104.56(15) . . ?
O1 S1 C19 109.74(15) . . ?
O2 S1 N1 106.92(15) . . ?
O2 S1 C19 108.21(15) . . ?
N1 S1 C19 107.17(14) . . ?
C2 O3 C1 118.7(2) . . ?
C1 N1 S1 120.8(2) . . ?
O3 C1 N1 106.8(2) . . ?
O3 C1 C14 110.7(2) . . ?
N1 C1 C14 110.6(3) . . ?
O3 C2 C3 122.7(3) . . ?
O3 C2 C18 115.7(3) . . ?
C18 C2 C3 121.5(3) . . ?
C2 C3 C4 120.6(3) . . ?
C2 C3 C15 117.2(3) . . ?
C15 C3 C4 122.2(3) . . ?
C3 C4 C5 110.0(3) . . ?
C3 C4 C14 109.0(3) . . ?
C5 C4 C14 113.2(3) . . ?
C6 C5 C4 116.0(3) . . ?
O4 C6 C5 120.9(3) . . ?
O4 C6 C7 121.2(3) . . ?
C7 C6 C5 117.8(3) . . ?
C8 C7 C6 122.9(3) . . ?
C8 C7 C12 117.3(4) . . ?
C12 C7 C6 119.7(3) . . ?
C9 C8 C7 121.7(4) . . ?
C10 C9 C8 121.4(4) . . ?
C9 C10 C11 118.0(4) . . ?
C9 C10 C13 121.6(5) . . ?
C11 C10 C13 120.5(5) . . ?
C10 C11 C12 121.6(4) . . ?
C7 C12 C11 120.1(4) . . ?
C1 C14 C4 111.0(3) . . ?
C16 C15 C3 121.3(4) . . ?
C17 C16 C15 120.2(3) . . ?
C16 C17 C18 120.1(4) . . ?
C17 C18 C2 119.7(4) . . ?
C20 C19 S1 119.7(3) . . ?
C20 C19 C24 119.2(3) . . ?
C24 C19 S1 120.9(3) . . ?
C19 C20 C21 119.7(4) . . ?
C22 C21 C20 121.9(4) . . ?
C21 C22 C23 117.4(4) . . ?
C21 C22 C25 122.2(4) . . ?
C23 C22 C25 120.4(5) . . ?
C22 C23 C24 121.5(4) . . ?
C19 C24 C23 120.2(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 N1 C1 O3 -76.9(3) . . . . ?
S1 N1 C1 C14 162.7(2) . . . . ?
S1 C19 C20 C21 -171.7(4) . . . . ?
S1 C19 C24 C23 172.9(4) . . . . ?
O1 S1 N1 C1 174.7(2) . . . . ?
O1 S1 C19 C20 -39.9(3) . . . . ?
O1 S1 C19 C24 145.2(3) . . . . ?
O2 S1 N1 C1 -57.6(3) . . . . ?
O2 S1 C19 C20 -172.0(3) . . . . ?
O2 S1 C19 C24 13.2(4) . . . . ?
O3 C1 C14 C4 59.0(4) . . . . ?
O3 C2 C3 C4 -5.9(5) . . . . ?
O3 C2 C3 C15 176.2(3) . . . . ?
O3 C2 C18 C17 -176.8(4) . . . . ?
O4 C6 C7 C8 -179.4(3) . . . . ?
O4 C6 C7 C12 3.6(5) . . . . ?
N1 S1 C19 C20 73.1(3) . . . . ?
N1 S1 C19 C24 -101.8(3) . . . . ?
N1 C1 C14 C4 177.1(2) . . . . ?
C1 O3 C2 C3 13.8(5) . . . . ?
C1 O3 C2 C18 -169.2(3) . . . . ?
C2 O3 C1 N1 -160.5(3) . . . . ?
C2 O3 C1 C14 -40.1(4) . . . . ?
C2 C3 C4 C5 -100.3(3) . . . . ?
C2 C3 C4 C14 24.4(4) . . . . ?
C2 C3 C15 C16 0.0(5) . . . . ?
C3 C2 C18 C17 0.3(6) . . . . ?
C3 C4 C5 C6 -166.7(2) . . . . ?
C3 C4 C14 C1 -50.0(4) . . . . ?
C3 C15 C16 C17 1.1(6) . . . . ?
C4 C3 C15 C16 -177.9(3) . . . . ?
C4 C5 C6 O4 3.0(4) . . . . ?
C4 C5 C6 C7 -179.7(3) . . . . ?
C5 C4 C14 C1 72.7(3) . . . . ?
C5 C6 C7 C8 3.3(5) . . . . ?
C5 C6 C7 C12 -173.8(3) . . . . ?
C6 C7 C8 C9 -176.7(4) . . . . ?
C6 C7 C12 C11 176.6(3) . . . . ?
C7 C8 C9 C10 -0.5(7) . . . . ?
C8 C7 C12 C11 -0.6(5) . . . . ?
C8 C9 C10 C11 0.6(7) . . . . ?
C8 C9 C10 C13 179.6(5) . . . . ?
C9 C10 C11 C12 -0.8(6) . . . . ?
C10 C11 C12 C7 0.8(6) . . . . ?
C12 C7 C8 C9 0.5(5) . . . . ?
C13 C10 C11 C12 -179.7(5) . . . . ?
C14 C4 C5 C6 71.1(3) . . . . ?
C15 C3 C4 C5 77.5(4) . . . . ?
C15 C3 C4 C14 -157.8(3) . . . . ?
C15 C16 C17 C18 -1.6(6) . . . . ?
C16 C17 C18 C2 0.9(6) . . . . ?
C18 C2 C3 C4 177.2(3) . . . . ?
C18 C2 C3 C15 -0.7(5) . . . . ?
C19 S1 N1 C1 58.2(3) . . . . ?
C19 C20 C21 C22 -1.6(8) . . . . ?
C20 C19 C24 C23 -2.0(6) . . . . ?
C20 C21 C22 C23 -1.3(8) . . . . ?
C20 C21 C22 C25 176.3(4) . . . . ?
C21 C22 C23 C24 2.6(7) . . . . ?
C22 C23 C24 C19 -1.0(8) . . . . ?
C24 C19 C20 C21 3.2(6) . . . . ?
C25 C22 C23 C24 -175.1(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_190125cyh_0m
_database_code_depnum_ccdc_archive 'CCDC 1911411'
loop_
_audit_author_name
_audit_author_address
'Yankai Liu'
;Ocean University of China
China
;
_audit_update_record             
;
2019-04-22 deposited with the CCDC.	2019-10-02 downloaded from the CCDC.
;
_audit_creation_date             2019-01-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H23 N O3 S'
_chemical_formula_sum            'C25 H23 N O3 S'
_chemical_formula_weight         417.50
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.784(3)
_cell_length_b                   9.976(3)
_cell_length_c                   12.349(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.656(5)
_cell_angle_gamma                90
_cell_volume                     1082.1(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3037
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.700
_cell_measurement_theta_min      2.624
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5206
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/3 (Bruker,2014/3) was used for absorption correction. wR2(int) was 0.0953 before and 0.0513 after correction. The Ratio of minimum to maximum transmission is 0.6982. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0571
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6538
_diffrn_reflns_point_group_measured_fraction_full 0.937
_diffrn_reflns_point_group_measured_fraction_max 0.885
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.696
_diffrn_reflns_theta_min         2.319
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_full    0.869
_reflns_Friedel_fraction_max     0.792
_reflns_number_gt                3665
_reflns_number_total             4490
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 1374 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_coef       0.034(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         4490
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0472
_refine_ls_restrained_S_all      1.033
_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)+(0.0741P)²+0.1330P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1244
_refine_ls_wR_factor_ref         0.1376
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C5(H5)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15),
 C16(H16), C17(H17), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.09797(9) 0.33861(11) 0.73239(6) 0.0529(3) Uani 1 1 d . . . . .
O1 O 0.0202(3) 0.4581(3) 0.7632(3) 0.0726(9) Uani 1 1 d . . . . .
O2 O 0.0328(4) 0.2105(3) 0.7569(2) 0.0719(9) Uani 1 1 d . . . . .
O3 O 0.3860(3) 0.5103(2) 0.68941(18) 0.0465(6) Uani 1 1 d . . . . .
N1 N 0.2687(3) 0.3370(4) 0.7937(2) 0.0482(6) Uani 1 1 d . . . . .
C1 C 0.3620(4) 0.4626(4) 0.7975(3) 0.0450(8) Uani 1 1 d . . . . .
C2 C 0.4935(4) 0.4455(4) 0.6272(3) 0.0446(7) Uani 1 1 d . . . . .
C3 C 0.5951(4) 0.3520(5) 0.6703(3) 0.0515(8) Uani 1 1 d . . . . .
C4 C 0.5882(4) 0.3148(5) 0.7889(3) 0.0603(11) Uani 1 1 d . . . . .
H4 H 0.691048 0.296379 0.816727 0.072 Uiso 1 1 calc R . . . .
C5 C 0.5180(4) 0.4305(4) 0.8518(3) 0.0544(9) Uani 1 1 d . . . . .
H5 H 0.498833 0.399230 0.925654 0.065 Uiso 1 1 calc R . . . .
C6 C 0.6193(5) 0.5530(5) 0.8592(4) 0.0704(12) Uani 1 1 d . . . . .
H6A H 0.625360 0.594575 0.789250 0.106 Uiso 1 1 calc GR . . . .
H6B H 0.719344 0.526715 0.882977 0.106 Uiso 1 1 calc GR . . . .
H6C H 0.577424 0.615405 0.909979 0.106 Uiso 1 1 calc GR . . . .
C7 C 0.4887(6) 0.1947(5) 0.8055(4) 0.0734(13) Uani 1 1 d . . . . .
H7 H 0.531451 0.110232 0.815144 0.088 Uiso 1 1 calc R . . . .
C8 C 0.3398(6) 0.2105(4) 0.8063(4) 0.0644(11) Uani 1 1 d . . . . .
H8 H 0.278762 0.135318 0.815515 0.077 Uiso 1 1 calc R . . . .
C9 C 0.7003(5) 0.2959(5) 0.5992(4) 0.0664(11) Uani 1 1 d . . . . .
H9 H 0.771216 0.234684 0.625781 0.080 Uiso 1 1 calc R . . . .
C10 C 0.7017(4) 0.3288(6) 0.4912(3) 0.0693(12) Uani 1 1 d . . . . .
H10 H 0.771854 0.288822 0.445549 0.083 Uiso 1 1 calc R . . . .
C11 C 0.6000(5) 0.4205(5) 0.4508(3) 0.0621(11) Uani 1 1 d . . . . .
H11 H 0.601614 0.442798 0.377674 0.075 Uiso 1 1 calc R . . . .
C12 C 0.4946(4) 0.4803(4) 0.5181(3) 0.0507(8) Uani 1 1 d . . . . .
H12 H 0.425618 0.542850 0.490802 0.061 Uiso 1 1 calc R . . . .
C13 C 0.2808(4) 0.5731(4) 0.8575(3) 0.0497(8) Uani 1 1 d . . . . .
C14 C 0.2150(5) 0.5455(5) 0.9571(3) 0.0621(11) Uani 1 1 d . . . . .
H14 H 0.218781 0.458702 0.984554 0.074 Uiso 1 1 calc R . . . .
C15 C 0.1445(6) 0.6445(6) 1.0155(4) 0.0764(13) Uani 1 1 d . . . . .
H15 H 0.100998 0.623979 1.081818 0.092 Uiso 1 1 calc R . . . .
C16 C 0.1377(6) 0.7717(6) 0.9773(4) 0.0821(15) Uani 1 1 d . . . . .
H16 H 0.087304 0.837615 1.016193 0.099 Uiso 1 1 calc R . . . .
C17 C 0.2066(7) 0.8035(5) 0.8794(5) 0.0902(16) Uani 1 1 d . . . . .
H17 H 0.206037 0.891437 0.854453 0.108 Uiso 1 1 calc R . . . .
C18 C 0.2764(6) 0.7032(5) 0.8190(3) 0.0677(11) Uani 1 1 d . . . . .
H18 H 0.319980 0.723779 0.752731 0.081 Uiso 1 1 calc R . . . .
C19 C 0.1267(3) 0.3440(4) 0.5918(2) 0.0422(6) Uani 1 1 d . . . . .
C20 C 0.1892(4) 0.2350(4) 0.5396(3) 0.0507(9) Uani 1 1 d . . . . .
H20 H 0.219889 0.159965 0.578833 0.061 Uiso 1 1 calc R . . . .
C21 C 0.2058(5) 0.2384(4) 0.4286(3) 0.0576(9) Uani 1 1 d . . . . .
H21 H 0.248638 0.165320 0.393448 0.069 Uiso 1 1 calc R . . . .
C22 C 0.1594(4) 0.3496(5) 0.3686(3) 0.0559(9) Uani 1 1 d . . . . .
C23 C 0.0960(5) 0.4564(4) 0.4223(4) 0.0603(10) Uani 1 1 d . . . . .
H23 H 0.063634 0.530892 0.382964 0.072 Uiso 1 1 calc R . . . .
C24 C 0.0794(4) 0.4553(4) 0.5335(3) 0.0545(9) Uani 1 1 d . . . . .
H24 H 0.036913 0.528447 0.568714 0.065 Uiso 1 1 calc R . . . .
C25 C 0.1800(7) 0.3539(7) 0.2470(4) 0.0933(17) Uani 1 1 d . . . . .
H25A H 0.286177 0.362829 0.230988 0.140 Uiso 1 1 calc GR . . . .
H25B H 0.125256 0.429108 0.217506 0.140 Uiso 1 1 calc GR . . . .
H25C H 0.141439 0.272636 0.215361 0.140 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 1.427(3) . ?
S1 O2 1.434(3) . ?
S1 N1 1.673(3) . ?
S1 C19 1.758(3) . ?
O3 C1 1.435(4) . ?
O3 C2 1.384(4) . ?
N1 C1 1.498(5) . ?
N1 C8 1.415(6) . ?
C1 C5 1.551(5) . ?
C1 C13 1.512(5) . ?
C2 C3 1.392(5) . ?
C2 C12 1.391(5) . ?
C3 C4 1.513(5) . ?
C3 C9 1.399(6) . ?
C4 H4 0.9800 . ?
C4 C5 1.526(6) . ?
C4 C7 1.498(6) . ?
C5 H5 0.9800 . ?
C5 C6 1.514(6) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7 0.9300 . ?
C7 C8 1.318(7) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.373(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.369(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.387(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.393(5) . ?
C13 C18 1.382(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.374(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.355(8) . ?
C16 H16 0.9300 . ?
C16 C17 1.394(8) . ?
C17 H17 0.9300 . ?
C17 C18 1.394(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.382(5) . ?
C19 C24 1.385(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.380(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.393(6) . ?
C22 C23 1.377(6) . ?
C22 C25 1.515(6) . ?
C23 H23 0.9300 . ?
C23 C24 1.383(6) . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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 119.65(18) . . ?
O1 S1 N1 108.48(17) . . ?
O1 S1 C19 108.2(2) . . ?
O2 S1 N1 104.70(18) . . ?
O2 S1 C19 107.31(17) . . ?
N1 S1 C19 108.01(13) . . ?
C2 O3 C1 118.0(3) . . ?
C1 N1 S1 119.6(2) . . ?
C8 N1 S1 116.8(3) . . ?
C8 N1 C1 120.1(3) . . ?
O3 C1 N1 109.5(3) . . ?
O3 C1 C5 109.4(3) . . ?
O3 C1 C13 106.8(3) . . ?
N1 C1 C5 108.7(3) . . ?
N1 C1 C13 111.4(3) . . ?
C13 C1 C5 111.0(3) . . ?
O3 C2 C3 122.6(3) . . ?
O3 C2 C12 115.6(3) . . ?
C12 C2 C3 121.7(3) . . ?
C2 C3 C4 120.1(3) . . ?
C2 C3 C9 117.0(4) . . ?
C9 C3 C4 122.9(4) . . ?
C3 C4 H4 109.8 . . ?
C3 C4 C5 109.1(3) . . ?
C5 C4 H4 109.8 . . ?
C7 C4 C3 111.0(3) . . ?
C7 C4 H4 109.8 . . ?
C7 C4 C5 107.1(3) . . ?
C1 C5 H5 107.9 . . ?
C4 C5 C1 107.2(3) . . ?
C4 C5 H5 107.9 . . ?
C6 C5 C1 112.0(3) . . ?
C6 C5 C4 113.6(3) . . ?
C6 C5 H5 107.9 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C7 H7 120.4 . . ?
C8 C7 C4 119.1(4) . . ?
C8 C7 H7 120.4 . . ?
N1 C8 H8 118.6 . . ?
C7 C8 N1 122.8(4) . . ?
C7 C8 H8 118.6 . . ?
C3 C9 H9 119.1 . . ?
C10 C9 C3 121.8(4) . . ?
C10 C9 H9 119.1 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.0(4) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.4(4) . . ?
C12 C11 H11 119.8 . . ?
C2 C12 H12 120.5 . . ?
C11 C12 C2 119.0(4) . . ?
C11 C12 H12 120.5 . . ?
C14 C13 C1 119.4(4) . . ?
C18 C13 C1 121.8(3) . . ?
C18 C13 C14 118.7(4) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 121.0(5) . . ?
C15 C14 H14 119.5 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.5(5) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.8(4) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 119.9(5) . . ?
C18 C17 H17 120.0 . . ?
C13 C18 C17 120.0(4) . . ?
C13 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
C20 C19 S1 120.0(3) . . ?
C20 C19 C24 120.4(3) . . ?
C24 C19 S1 119.5(3) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 C19 119.5(3) . . ?
C21 C20 H20 120.3 . . ?
C20 C21 H21 119.5 . . ?
C20 C21 C22 121.0(4) . . ?
C22 C21 H21 119.5 . . ?
C21 C22 C25 120.9(4) . . ?
C23 C22 C21 118.6(3) . . ?
C23 C22 C25 120.6(4) . . ?
C22 C23 H23 119.3 . . ?
C22 C23 C24 121.3(3) . . ?
C24 C23 H23 119.3 . . ?
C19 C24 H24 120.4 . . ?
C23 C24 C19 119.3(4) . . ?
C23 C24 H24 120.4 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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 N1 C1 O3 -56.8(3) . . . . ?
S1 N1 C1 C5 -176.3(2) . . . . ?
S1 N1 C1 C13 61.1(3) . . . . ?
S1 N1 C8 C7 148.4(4) . . . . ?
S1 C19 C20 C21 177.5(3) . . . . ?
S1 C19 C24 C23 -177.1(3) . . . . ?
O1 S1 N1 C1 -43.3(3) . . . . ?
O1 S1 N1 C8 157.8(3) . . . . ?
O1 S1 C19 C20 -174.9(3) . . . . ?
O1 S1 C19 C24 2.0(3) . . . . ?
O2 S1 N1 C1 -172.1(2) . . . . ?
O2 S1 N1 C8 29.0(3) . . . . ?
O2 S1 C19 C20 -44.5(3) . . . . ?
O2 S1 C19 C24 132.4(3) . . . . ?
O3 C1 C5 C4 -64.7(4) . . . . ?
O3 C1 C5 C6 60.6(4) . . . . ?
O3 C1 C13 C14 166.9(3) . . . . ?
O3 C1 C13 C18 -16.4(5) . . . . ?
O3 C2 C3 C4 1.7(5) . . . . ?
O3 C2 C3 C9 -178.6(3) . . . . ?
O3 C2 C12 C11 179.4(3) . . . . ?
N1 S1 C19 C20 67.9(3) . . . . ?
N1 S1 C19 C24 -115.3(3) . . . . ?
N1 C1 C5 C4 54.9(4) . . . . ?
N1 C1 C5 C6 -179.8(3) . . . . ?
N1 C1 C13 C14 47.4(4) . . . . ?
N1 C1 C13 C18 -136.0(4) . . . . ?
C1 O3 C2 C3 -10.8(5) . . . . ?
C1 O3 C2 C12 169.6(3) . . . . ?
C1 N1 C8 C7 -10.4(6) . . . . ?
C1 C13 C14 C15 177.9(4) . . . . ?
C1 C13 C18 C17 -176.9(4) . . . . ?
C2 O3 C1 N1 -76.8(3) . . . . ?
C2 O3 C1 C5 42.3(4) . . . . ?
C2 O3 C1 C13 162.4(3) . . . . ?
C2 C3 C4 C5 -25.4(5) . . . . ?
C2 C3 C4 C7 92.5(5) . . . . ?
C2 C3 C9 C10 -1.4(6) . . . . ?
C3 C2 C12 C11 -0.1(5) . . . . ?
C3 C4 C5 C1 54.7(4) . . . . ?
C3 C4 C5 C6 -69.6(4) . . . . ?
C3 C4 C7 C8 -79.7(5) . . . . ?
C3 C9 C10 C11 1.1(7) . . . . ?
C4 C3 C9 C10 178.3(4) . . . . ?
C4 C7 C8 N1 -1.0(7) . . . . ?
C5 C1 C13 C14 -73.9(4) . . . . ?
C5 C1 C13 C18 102.7(4) . . . . ?
C5 C4 C7 C8 39.4(5) . . . . ?
C7 C4 C5 C1 -65.6(4) . . . . ?
C7 C4 C5 C6 170.1(3) . . . . ?
C8 N1 C1 O3 101.4(4) . . . . ?
C8 N1 C1 C5 -18.1(4) . . . . ?
C8 N1 C1 C13 -140.7(3) . . . . ?
C9 C3 C4 C5 154.9(4) . . . . ?
C9 C3 C4 C7 -87.2(5) . . . . ?
C9 C10 C11 C12 -0.3(7) . . . . ?
C10 C11 C12 C2 -0.2(6) . . . . ?
C12 C2 C3 C4 -178.8(3) . . . . ?
C12 C2 C3 C9 0.9(6) . . . . ?
C13 C1 C5 C4 177.8(3) . . . . ?
C13 C1 C5 C6 -57.0(4) . . . . ?
C13 C14 C15 C16 -0.1(7) . . . . ?
C14 C13 C18 C17 -0.2(7) . . . . ?
C14 C15 C16 C17 -1.9(8) . . . . ?
C15 C16 C17 C18 2.8(8) . . . . ?
C16 C17 C18 C13 -1.7(8) . . . . ?
C18 C13 C14 C15 1.1(6) . . . . ?
C19 S1 N1 C1 73.7(3) . . . . ?
C19 S1 N1 C8 -85.2(3) . . . . ?
C19 C20 C21 C22 -0.5(6) . . . . ?
C20 C19 C24 C23 -0.2(5) . . . . ?
C20 C21 C22 C23 -0.2(6) . . . . ?
C20 C21 C22 C25 179.1(4) . . . . ?
C21 C22 C23 C24 0.6(6) . . . . ?
C22 C23 C24 C19 -0.4(6) . . . . ?
C24 C19 C20 C21 0.7(5) . . . . ?
C25 C22 C23 C24 -178.6(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
