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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_20190904d_0m
_database_code_depnum_ccdc_archive 'CCDC 2011625'
loop_
_audit_author_name
_audit_author_address
'Q. Ni'
;Anhui Normal University
China
;
_audit_update_record             
;
2020-06-23 deposited with the CCDC.	2020-08-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H16 N2 O S'
_chemical_formula_weight         332.41

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                   11.0500(4)
_cell_length_b                   14.7669(6)
_cell_length_c                   11.3282(4)
_cell_angle_alpha                90
_cell_angle_beta                 109.477(2)
_cell_angle_gamma                90
_cell_volume                     1742.69(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9978
_cell_measurement_theta_min      3.15
_cell_measurement_theta_max      27.52

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.194
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(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            72425
_diffrn_reflns_av_unetI/netI     0.0136
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.154
_diffrn_reflns_theta_max         27.561
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4021
_reflns_number_gt                3414
_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-2018/1 (Sheldrick, 2018)'
_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)+(0.0484P)²+0.7698P] 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     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0176(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4021
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1165
_refine_ls_wR_factor_gt          0.1050
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.001
_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 0.56110(15) 0.27492(11) 0.45647(15) 0.0460(3) Uani 1 1 d . . . . .
C2 C 0.65060(19) 0.23779(14) 0.4081(2) 0.0635(5) Uani 1 1 d . . . . .
H2 H 0.632523 0.184909 0.360830 0.076 Uiso 1 1 calc R U . . .
C3 C 0.7667(2) 0.28142(16) 0.4320(2) 0.0747(6) Uani 1 1 d . . . . .
H3 H 0.827823 0.256957 0.401263 0.090 Uiso 1 1 calc R U . . .
C4 C 0.79410(19) 0.36084(18) 0.5007(2) 0.0758(6) Uani 1 1 d . . . . .
H4 H 0.873849 0.388038 0.516448 0.091 Uiso 1 1 calc R U . . .
C5 C 0.70647(18) 0.40010(15) 0.5459(2) 0.0680(5) Uani 1 1 d . . . . .
H5 H 0.724299 0.454320 0.590109 0.082 Uiso 1 1 calc R U . . .
C6 C 0.58919(15) 0.35591(12) 0.52336(15) 0.0484(4) Uani 1 1 d . . . . .
C7 C 0.38260(13) 0.28834(10) 0.50030(13) 0.0386(3) Uani 1 1 d . . . . .
C8 C 0.25034(13) 0.26266(9) 0.50184(13) 0.0389(3) Uani 1 1 d . . . . .
C9 C 0.25589(16) 0.16857(11) 0.56581(16) 0.0513(4) Uani 1 1 d . . . . .
H9A H 0.303370 0.126436 0.532166 0.062 Uiso 1 1 calc R U . . .
H9B H 0.301001 0.174423 0.654996 0.062 Uiso 1 1 calc R U . . .
C10 C 0.12374(18) 0.13187(11) 0.54489(18) 0.0560(4) Uani 1 1 d . . . . .
C11 C 0.03923(18) 0.13563(11) 0.41180(19) 0.0591(5) Uani 1 1 d . . . . .
H11A H 0.071647 0.094596 0.362504 0.071 Uiso 1 1 calc R U . . .
H11B H -0.046541 0.116062 0.405359 0.071 Uiso 1 1 calc R U . . .
C12 C 0.15584(13) 0.25608(10) 0.36331(14) 0.0396(3) Uani 1 1 d . . . . .
H12 H 0.189972 0.211395 0.318684 0.047 Uiso 1 1 calc R U . . .
C13 C 0.0856(3) 0.09914(16) 0.6347(2) 0.0852(7) Uani 1 1 d . . . . .
H13A H 0.002445 0.077070 0.616115 0.102 Uiso 1 1 calc R U . . .
H13B H 0.141692 0.098094 0.716814 0.102 Uiso 1 1 calc R U . . .
C14 C 0.20381(15) 0.33049(11) 0.57238(15) 0.0476(4) Uani 1 1 d . . . . .
C15 C 0.13739(13) 0.34435(10) 0.29256(13) 0.0387(3) Uani 1 1 d . . . . .
C16 C 0.04801(14) 0.40774(11) 0.30166(15) 0.0455(3) Uani 1 1 d . . . . .
H16 H 0.000035 0.396347 0.353673 0.055 Uiso 1 1 calc R U . . .
C17 C 0.02962(17) 0.48764(11) 0.23416(17) 0.0549(4) Uani 1 1 d . . . . .
H17 H -0.030610 0.529506 0.240902 0.066 Uiso 1 1 calc R U . . .
C18 C 0.1002(2) 0.50533(13) 0.15705(17) 0.0615(5) Uani 1 1 d . . . . .
H18 H 0.087655 0.558858 0.111279 0.074 Uiso 1 1 calc R U . . .
C19 C 0.1897(2) 0.44312(14) 0.14823(17) 0.0634(5) Uani 1 1 d . . . . .
H19 H 0.238403 0.455355 0.097144 0.076 Uiso 1 1 calc R U . . .
C20 C 0.20807(17) 0.36237(12) 0.21469(15) 0.0518(4) Uani 1 1 d . . . . .
H20 H 0.267754 0.320435 0.206917 0.062 Uiso 1 1 calc R U . . .
N1 N 0.44219(12) 0.23784(9) 0.44507(13) 0.0462(3) Uani 1 1 d . . . . .
N2 N 0.16985(18) 0.38131(13) 0.62914(17) 0.0726(5) Uani 1 1 d . . . . .
O1 O 0.03374(10) 0.22584(7) 0.36279(11) 0.0507(3) Uani 1 1 d . . . . .
S1 S 0.46119(4) 0.38646(3) 0.57024(4) 0.05318(15) 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 1.389(2) . ?
C1 C2 1.393(2) . ?
C1 C6 1.394(2) . ?
C2 C3 1.379(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.384(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.366(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(2) . ?
C5 H5 0.9300 . ?
C6 S1 1.7283(17) . ?
C7 N1 1.2868(19) . ?
C7 C8 1.5156(19) . ?
C7 S1 1.7385(15) . ?
C8 C14 1.477(2) . ?
C8 C9 1.559(2) . ?
C8 C12 1.572(2) . ?
C9 C10 1.500(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C13 1.317(3) . ?
C10 C11 1.486(3) . ?
C11 O1 1.4367(19) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 O1 1.4194(17) . ?
C12 C15 1.508(2) . ?
C12 H12 0.9800 . ?
C13 H13A 0.9300 . ?
C13 H13B 0.9300 . ?
C14 N2 1.131(2) . ?
C15 C20 1.385(2) . ?
C15 C16 1.389(2) . ?
C16 C17 1.384(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.376(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.377(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.389(2) . ?
C19 H19 0.9300 . ?
C20 H20 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
N1 C1 C2 125.58(16) . . ?
N1 C1 C6 114.89(14) . . ?
C2 C1 C6 119.53(16) . . ?
C3 C2 C1 118.34(19) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 121.40(19) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C5 C4 C3 121.38(19) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 117.6(2) . . ?
C4 C5 H5 121.2 . . ?
C6 C5 H5 121.2 . . ?
C1 C6 C5 121.68(16) . . ?
C1 C6 S1 109.52(12) . . ?
C5 C6 S1 128.79(15) . . ?
N1 C7 C8 120.82(13) . . ?
N1 C7 S1 116.47(11) . . ?
C8 C7 S1 122.71(10) . . ?
C14 C8 C7 110.34(12) . . ?
C14 C8 C9 108.66(13) . . ?
C7 C8 C9 109.86(12) . . ?
C14 C8 C12 110.30(12) . . ?
C7 C8 C12 109.04(11) . . ?
C9 C8 C12 108.61(12) . . ?
C10 C9 C8 111.29(13) . . ?
C10 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C13 C10 C11 122.9(2) . . ?
C13 C10 C9 123.8(2) . . ?
C11 C10 C9 113.32(15) . . ?
O1 C11 C10 110.97(14) . . ?
O1 C11 H11A 109.4 . . ?
C10 C11 H11A 109.4 . . ?
O1 C11 H11B 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
O1 C12 C15 108.05(11) . . ?
O1 C12 C8 109.74(12) . . ?
C15 C12 C8 113.86(11) . . ?
O1 C12 H12 108.4 . . ?
C15 C12 H12 108.4 . . ?
C8 C12 H12 108.4 . . ?
C10 C13 H13A 120.0 . . ?
C10 C13 H13B 120.0 . . ?
H13A C13 H13B 120.0 . . ?
N2 C14 C8 178.24(19) . . ?
C20 C15 C16 118.92(14) . . ?
C20 C15 C12 119.97(13) . . ?
C16 C15 C12 121.09(13) . . ?
C17 C16 C15 120.70(15) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C18 C17 C16 120.17(17) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 119.47(16) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
C18 C19 C20 120.81(17) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C15 C20 C19 119.92(16) . . ?
C15 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C7 N1 C1 110.36(13) . . ?
C12 O1 C11 111.87(12) . . ?
C6 S1 C7 88.74(7) . . ?

_refine_diff_density_max         0.231
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.038



