# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_20210630_gaoy_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2094464'
loop_
_audit_author_name
_audit_author_address
'Yang Simin'
;Guangdong University of Technology
China
;
_audit_update_record             
;
2021-07-05 deposited with the CCDC.	2022-01-27 downloaded from the CCDC.
;
_audit_creation_date             2021-07-01
_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         'C20 H14 N2 O S'
_chemical_formula_sum            'C20 H14 N2 O S'
_chemical_formula_weight         330.39
_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           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                   15.6620(4)
_cell_length_b                   10.0274(2)
_cell_length_c                   10.2923(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.5450(10)
_cell_angle_gamma                90
_cell_volume                     1564.59(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5972
_cell_measurement_temperature    230(2)
_cell_measurement_theta_max      26.31
_cell_measurement_theta_min      2.69
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6410
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1335 before and 0.0473 after correction.
The Ratio of minimum to maximum transmission is 0.8599.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9101
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         2.435
_diffrn_ambient_temperature      230.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2483
_reflns_number_total             3165
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0420
_refine_ls_restrained_S_all      1.082
_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)+(0.0566P)²+0.2841P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1213
_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 Aromatic/amide H refined with riding coordinates:
 C005(H005), C008(H008), C009(H009), C00G(H00G), C00H(H00H), C00I(H00I),
 C00J(H00J), C00K(H00K), C00M(H00M), C00N(H00N), C00O(H00O)
2.b Idealised Me refined as rotating group:
 C00F(H00A,H00B,H00C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
S001 S 0.67164(3) 0.56647(5) 0.76200(5) 0.04781(18) Uani 1 1 d . . . . .
O002 O 0.35422(9) 0.45783(15) 0.83220(14) 0.0586(4) Uani 1 1 d . . . . .
N003 N 0.67286(10) 0.35289(15) 0.56053(15) 0.0422(4) Uani 1 1 d . . . . .
C004 C 0.59288(11) 0.36358(16) 0.59676(17) 0.0375(4) Uani 1 1 d . . . . .
C005 C 0.44070(12) 0.30130(18) 0.57331(18) 0.0429(4) Uani 1 1 d . . . . .
H005 H 0.391621 0.249663 0.530359 0.051 Uiso 1 1 calc R . . . .
C006 C 0.58430(11) 0.45615(17) 0.69493(18) 0.0385(4) Uani 1 1 d . . . . .
C007 C 0.43269(12) 0.39253(18) 0.67135(18) 0.0411(4) Uani 1 1 d . . . . .
C008 C 0.50652(11) 0.46807(18) 0.73326(18) 0.0406(4) Uani 1 1 d . . . . .
H008 H 0.503109 0.527909 0.802073 0.049 Uiso 1 1 calc R . . . .
C009 C 0.51928(12) 0.28532(18) 0.53807(18) 0.0432(4) Uani 1 1 d . . . . .
H009 H 0.523565 0.220906 0.473654 0.052 Uiso 1 1 calc R . . . .
C00A C 0.75276(12) 0.36438(18) 0.66052(19) 0.0428(4) Uani 1 1 d . . . . .
C00B C 0.26235(12) 0.38959(18) 0.6437(2) 0.0449(5) Uani 1 1 d . . . . .
C00C C 0.34922(12) 0.41000(18) 0.70801(19) 0.0436(4) Uani 1 1 d . . . . .
C00D C 0.76047(12) 0.45870(18) 0.7630(2) 0.0439(4) Uani 1 1 d . . . . .
N00E N 0.26887(12) 0.4702(2) 0.8536(2) 0.0722(6) Uani 1 1 d . . . . .
C00F C 0.67440(14) 0.2756(2) 0.44074(19) 0.0515(5) Uani 1 1 d . . . . .
H00A H 0.675197 0.181218 0.461520 0.077 Uiso 1 1 calc GR . . . .
H00B H 0.726745 0.298381 0.411284 0.077 Uiso 1 1 calc GR . . . .
H00C H 0.622276 0.296026 0.369892 0.077 Uiso 1 1 calc GR . . . .
C00G C 0.83803(13) 0.4712(2) 0.8622(2) 0.0577(5) Uani 1 1 d . . . . .
H00G H 0.841965 0.533665 0.931528 0.069 Uiso 1 1 calc R . . . .
C00H C 0.82530(13) 0.2842(2) 0.6605(2) 0.0555(5) Uani 1 1 d . . . . .
H00H H 0.821514 0.219533 0.593203 0.067 Uiso 1 1 calc R . . . .
C00I C 0.21523(13) 0.3468(2) 0.5148(2) 0.0575(5) Uani 1 1 d . . . . .
H00I H 0.244945 0.321986 0.449757 0.069 Uiso 1 1 calc R . . . .
C00J C 0.90992(14) 0.3919(3) 0.8596(3) 0.0719(7) Uani 1 1 d . . . . .
H00J H 0.963093 0.401225 0.926027 0.086 Uiso 1 1 calc R . . . .
C00K C 0.90275(14) 0.2993(3) 0.7590(3) 0.0700(7) Uani 1 1 d . . . . .
H00K H 0.951496 0.245302 0.757153 0.084 Uiso 1 1 calc R . . . .
C00L C 0.21615(14) 0.4292(2) 0.7400(2) 0.0559(5) Uani 1 1 d . . . . .
C00M C 0.08006(15) 0.3804(3) 0.5854(3) 0.0765(7) Uani 1 1 d . . . . .
H00M H 0.018139 0.375542 0.562671 0.092 Uiso 1 1 calc R . . . .
C00N C 0.12618(15) 0.3427(3) 0.4876(3) 0.0730(7) Uani 1 1 d . . . . .
H00N H 0.093861 0.314241 0.402417 0.088 Uiso 1 1 calc R . . . .
C00O C 0.12207(15) 0.4225(3) 0.7081(3) 0.0718(7) Uani 1 1 d . . . . .
H00O H 0.090736 0.446922 0.771264 0.086 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
S001 C006 1.7599(18) . ?
S001 C00D 1.7596(19) . ?
O002 C00C 1.349(2) . ?
O002 N00E 1.414(2) . ?
N003 C004 1.398(2) . ?
N003 C00A 1.411(2) . ?
N003 C00F 1.461(2) . ?
C004 C006 1.403(2) . ?
C004 C009 1.400(2) . ?
C005 H005 0.9400 . ?
C005 C007 1.391(3) . ?
C005 C009 1.377(3) . ?
C006 C008 1.377(2) . ?
C007 C008 1.395(3) . ?
C007 C00C 1.459(3) . ?
C008 H008 0.9400 . ?
C009 H009 0.9400 . ?
C00A C00D 1.399(3) . ?
C00A C00H 1.392(3) . ?
C00B C00C 1.371(3) . ?
C00B C00I 1.413(3) . ?
C00B C00L 1.422(3) . ?
C00D C00G 1.382(3) . ?
N00E C00L 1.317(3) . ?
C00F H00A 0.9700 . ?
C00F H00B 0.9700 . ?
C00F H00C 0.9700 . ?
C00G H00G 0.9400 . ?
C00G C00J 1.384(3) . ?
C00H H00H 0.9400 . ?
C00H C00K 1.380(3) . ?
C00I H00I 0.9400 . ?
C00I C00N 1.352(3) . ?
C00J H00J 0.9400 . ?
C00J C00K 1.374(3) . ?
C00K H00K 0.9400 . ?
C00L C00O 1.428(3) . ?
C00M H00M 0.9400 . ?
C00M C00N 1.429(4) . ?
C00M C00O 1.338(4) . ?
C00N H00N 0.9400 . ?
C00O H00O 0.9400 . ?

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
C006 S001 C00D 98.73(8) . . ?
C00C O002 N00E 110.28(15) . . ?
C004 N003 C00A 119.28(14) . . ?
C004 N003 C00F 118.13(15) . . ?
C00A N003 C00F 117.33(15) . . ?
N003 C004 C006 119.81(15) . . ?
N003 C004 C009 122.54(16) . . ?
C009 C004 C006 117.65(16) . . ?
C007 C005 H005 119.4 . . ?
C009 C005 H005 119.4 . . ?
C009 C005 C007 121.13(17) . . ?
C004 C006 S001 119.52(13) . . ?
C008 C006 S001 119.32(13) . . ?
C008 C006 C004 121.03(16) . . ?
C005 C007 C008 118.23(16) . . ?
C005 C007 C00C 121.09(16) . . ?
C008 C007 C00C 120.68(17) . . ?
C006 C008 C007 120.90(17) . . ?
C006 C008 H008 119.6 . . ?
C007 C008 H008 119.6 . . ?
C004 C009 H009 119.5 . . ?
C005 C009 C004 120.98(17) . . ?
C005 C009 H009 119.5 . . ?
C00D C00A N003 119.85(16) . . ?
C00H C00A N003 121.82(18) . . ?
C00H C00A C00D 118.33(18) . . ?
C00C C00B C00I 136.04(19) . . ?
C00C C00B C00L 103.82(18) . . ?
C00I C00B C00L 120.10(18) . . ?
O002 C00C C007 116.43(16) . . ?
O002 C00C C00B 108.96(16) . . ?
C00B C00C C007 134.61(18) . . ?
C00A C00D S001 119.50(14) . . ?
C00G C00D S001 119.70(16) . . ?
C00G C00D C00A 120.76(18) . . ?
C00L N00E O002 103.94(17) . . ?
N003 C00F H00A 109.5 . . ?
N003 C00F H00B 109.5 . . ?
N003 C00F H00C 109.5 . . ?
H00A C00F H00B 109.5 . . ?
H00A C00F H00C 109.5 . . ?
H00B C00F H00C 109.5 . . ?
C00D C00G H00G 119.9 . . ?
C00D C00G C00J 120.1(2) . . ?
C00J C00G H00G 119.9 . . ?
C00A C00H H00H 119.9 . . ?
C00K C00H C00A 120.3(2) . . ?
C00K C00H H00H 119.9 . . ?
C00B C00I H00I 120.9 . . ?
C00N C00I C00B 118.2(2) . . ?
C00N C00I H00I 120.9 . . ?
C00G C00J H00J 120.3 . . ?
C00K C00J C00G 119.3(2) . . ?
C00K C00J H00J 120.3 . . ?
C00H C00K H00K 119.4 . . ?
C00J C00K C00H 121.2(2) . . ?
C00J C00K H00K 119.4 . . ?
C00B C00L C00O 120.2(2) . . ?
N00E C00L C00B 113.00(19) . . ?
N00E C00L C00O 126.8(2) . . ?
C00N C00M H00M 118.9 . . ?
C00O C00M H00M 118.9 . . ?
C00O C00M C00N 122.2(2) . . ?
C00I C00N C00M 121.6(2) . . ?
C00I C00N H00N 119.2 . . ?
C00M C00N H00N 119.2 . . ?
C00L C00O H00O 121.1 . . ?
C00M C00O C00L 117.8(2) . . ?
C00M C00O H00O 121.1 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
