# 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. 
# 
#######################################################################

data_mo_d8v18258_0m
_database_code_depnum_ccdc_archive 'CCDC 1877280'
loop_
_audit_author_name
_audit_author_address
'zhao zibiao'
;Dalian Institute of Chemical Physics,Chinese Academy of Sciences
China
;
_audit_update_record             
;
2018-11-06 deposited with the CCDC.	2019-03-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H15 N O2 S'
_chemical_formula_weight         321.38

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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, y+1/2, -z'

_cell_length_a                   8.0275(15)
_cell_length_b                   8.0254(17)
_cell_length_c                   12.699(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.787(7)
_cell_angle_gamma                90
_cell_volume                     800.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9676
_cell_measurement_theta_min      5.184
_cell_measurement_theta_max      54.894

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.211
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6340
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_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            13998
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.592
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             3112
_reflns_number_gt                3036
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.863
_reflns_Friedel_fraction_max     0.992
_reflns_Friedel_fraction_full    0.992

_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-2013 (Sheldrick, 2013)'
_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)+(0.0469P)²+0.0462P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1372 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.05(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3112
_refine_ls_number_parameters     213
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0285
_refine_ls_wR_factor_ref         0.0784
_refine_ls_wR_factor_gt          0.0777
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
S1 S 0.11718(6) 0.75892(7) 0.58186(4) 0.03940(19) Uani 1 1 d . . . . .
O1 O -0.0210(2) 0.7890(3) 0.49234(15) 0.0579(5) Uani 1 1 d . . . . .
O2 O 0.1620(2) 0.8864(2) 0.66037(16) 0.0544(5) Uani 1 1 d . . . . .
N1 N 0.0668(2) 0.5926(3) 0.64085(16) 0.0409(4) Uani 1 1 d . . . . .
C1 C 0.2986(3) 0.7045(3) 0.53201(17) 0.0384(5) Uani 1 1 d . . . . .
C2 C 0.2863(3) 0.6994(3) 0.42165(19) 0.0502(6) Uani 1 1 d . . . . .
H2 H 0.1829 0.7197 0.3750 0.060 Uiso 1 1 calc R U . . .
C3 C 0.4307(4) 0.6636(4) 0.3822(2) 0.0602(7) Uani 1 1 d . . . . .
H3 H 0.4247 0.6591 0.3084 0.072 Uiso 1 1 calc R U . . .
C4 C 0.5827(4) 0.6349(4) 0.4518(2) 0.0592(7) Uani 1 1 d . . . . .
H4 H 0.6799 0.6139 0.4247 0.071 Uiso 1 1 calc R U . . .
C5 C 0.5925(3) 0.6368(4) 0.5616(2) 0.0524(6) Uani 1 1 d . . . . .
H5 H 0.6963 0.6150 0.6075 0.063 Uiso 1 1 calc R U . . .
C6 C 0.4506(3) 0.6707(3) 0.60517(18) 0.0390(5) Uani 1 1 d . . . . .
C7 C 0.4649(3) 0.6760(3) 0.72388(18) 0.0412(5) Uani 1 1 d . . . . .
C8 C 0.6029(3) 0.7603(4) 0.7854(2) 0.0567(6) Uani 1 1 d . . . . .
H8 H 0.6822 0.8104 0.7515 0.068 Uiso 1 1 calc R U . . .
C9 C 0.6238(4) 0.7709(5) 0.8959(2) 0.0716(8) Uani 1 1 d . . . . .
H9 H 0.7174 0.8264 0.9359 0.086 Uiso 1 1 calc R U . . .
C10 C 0.5062(4) 0.6994(5) 0.9461(2) 0.0738(9) Uani 1 1 d . . . . .
H10 H 0.5184 0.7082 1.0204 0.089 Uiso 1 1 calc R U . . .
C11 C 0.3692(3) 0.6140(4) 0.88629(19) 0.0547(6) Uani 1 1 d . . . . .
H11 H 0.2907 0.5645 0.9212 0.066 Uiso 1 1 calc R U . . .
C12 C 0.3467(3) 0.6006(3) 0.77567(17) 0.0385(5) Uani 1 1 d . . . . .
C13 C 0.2027(3) 0.4940(3) 0.71188(16) 0.0349(5) Uani 1 1 d . . . . .
H13 H 0.2532 0.4205 0.6653 0.042 Uiso 1 1 calc R U . . .
C14 C 0.1129(3) 0.3842(3) 0.77952(16) 0.0393(5) Uani 1 1 d . . . . .
C15 C 0.1564(4) 0.2193(3) 0.79406(19) 0.0511(6) Uani 1 1 d . . . . .
H15 H 0.2440 0.1766 0.7641 0.061 Uiso 1 1 calc R U . . .
C16 C 0.0718(5) 0.1156(4) 0.8526(2) 0.0744(9) Uani 1 1 d . . . . .
H16 H 0.1021 0.0039 0.8615 0.089 Uiso 1 1 calc R U . . .
C17 C -0.0569(5) 0.1777(5) 0.8977(3) 0.0786(11) Uani 1 1 d . . . . .
H17 H -0.1136 0.1082 0.9373 0.094 Uiso 1 1 calc R U . . .
C18 C -0.1019(5) 0.3424(5) 0.8840(3) 0.0715(10) Uani 1 1 d . . . . .
H18 H -0.1884 0.3846 0.9151 0.086 Uiso 1 1 calc R U . . .
C19 C -0.0194(4) 0.4454(4) 0.8246(2) 0.0544(6) Uani 1 1 d . . . . .
H19 H -0.0521 0.5564 0.8145 0.065 Uiso 1 1 calc R U . . .
H1 H 0.002(4) 0.523(4) 0.591(2) 0.050(7) Uiso 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
S1 O2 1.4225(19) . ?
S1 O1 1.4373(18) . ?
S1 N1 1.622(2) . ?
S1 C1 1.758(2) . ?
N1 C13 1.493(3) . ?
N1 H1 0.93(3) . ?
C1 C2 1.385(3) . ?
C1 C6 1.400(3) . ?
C2 C3 1.383(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.489(3) . ?
C7 C8 1.394(3) . ?
C7 C12 1.398(3) . ?
C8 C9 1.380(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.369(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.384(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.383(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.530(3) . ?
C13 C14 1.513(3) . ?
C13 H13 0.9800 . ?
C14 C15 1.372(4) . ?
C14 C19 1.394(3) . ?
C15 C16 1.383(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.373(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.372(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.377(4) . ?
C18 H18 0.9300 . ?
C19 H19 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
O2 S1 O1 118.51(12) . . ?
O2 S1 N1 108.63(11) . . ?
O1 S1 N1 106.16(11) . . ?
O2 S1 C1 108.76(11) . . ?
O1 S1 C1 108.63(11) . . ?
N1 S1 C1 105.37(10) . . ?
C13 N1 S1 119.64(14) . . ?
C13 N1 H1 109.5(18) . . ?
S1 N1 H1 109.9(17) . . ?
C2 C1 C6 122.6(2) . . ?
C2 C1 S1 118.58(17) . . ?
C6 C1 S1 118.86(16) . . ?
C3 C2 C1 118.7(2) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.5(2) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 121.4(2) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 116.6(2) . . ?
C5 C6 C7 120.5(2) . . ?
C1 C6 C7 122.88(19) . . ?
C8 C7 C12 119.0(2) . . ?
C8 C7 C6 118.0(2) . . ?
C12 C7 C6 123.00(19) . . ?
C9 C8 C7 121.2(3) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C10 C9 C8 119.7(2) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C11 119.9(2) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C10 C11 C12 121.4(3) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C11 C12 C7 118.9(2) . . ?
C11 C12 C13 120.6(2) . . ?
C7 C12 C13 120.31(18) . . ?
N1 C13 C14 106.09(17) . . ?
N1 C13 C12 113.79(18) . . ?
C14 C13 C12 114.92(17) . . ?
N1 C13 H13 107.2 . . ?
C14 C13 H13 107.2 . . ?
C12 C13 H13 107.2 . . ?
C15 C14 C19 118.6(2) . . ?
C15 C14 C13 120.0(2) . . ?
C19 C14 C13 121.3(2) . . ?
C14 C15 C16 120.9(3) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 120.0(3) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C18 C17 C16 119.9(3) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C19 120.3(4) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C14 120.4(3) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?

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
O2 S1 N1 C13 -72.38(19) . . . . ?
O1 S1 N1 C13 159.15(17) . . . . ?
C1 S1 N1 C13 44.03(19) . . . . ?
O2 S1 C1 C2 -129.8(2) . . . . ?
O1 S1 C1 C2 0.5(2) . . . . ?
N1 S1 C1 C2 113.9(2) . . . . ?
O2 S1 C1 C6 49.1(2) . . . . ?
O1 S1 C1 C6 179.42(18) . . . . ?
N1 S1 C1 C6 -67.2(2) . . . . ?
C6 C1 C2 C3 -1.6(4) . . . . ?
S1 C1 C2 C3 177.2(2) . . . . ?
C1 C2 C3 C4 -0.4(4) . . . . ?
C2 C3 C4 C5 1.8(5) . . . . ?
C3 C4 C5 C6 -1.2(5) . . . . ?
C4 C5 C6 C1 -0.7(4) . . . . ?
C4 C5 C6 C7 -178.6(3) . . . . ?
C2 C1 C6 C5 2.1(3) . . . . ?
S1 C1 C6 C5 -176.73(19) . . . . ?
C2 C1 C6 C7 180.0(2) . . . . ?
S1 C1 C6 C7 1.1(3) . . . . ?
C5 C6 C7 C8 44.5(3) . . . . ?
C1 C6 C7 C8 -133.2(3) . . . . ?
C5 C6 C7 C12 -135.5(3) . . . . ?
C1 C6 C7 C12 46.7(3) . . . . ?
C12 C7 C8 C9 -0.3(5) . . . . ?
C6 C7 C8 C9 179.7(3) . . . . ?
C7 C8 C9 C10 -0.8(6) . . . . ?
C8 C9 C10 C11 1.4(6) . . . . ?
C9 C10 C11 C12 -0.8(5) . . . . ?
C10 C11 C12 C7 -0.3(4) . . . . ?
C10 C11 C12 C13 175.0(3) . . . . ?
C8 C7 C12 C11 0.8(4) . . . . ?
C6 C7 C12 C11 -179.1(2) . . . . ?
C8 C7 C12 C13 -174.5(2) . . . . ?
C6 C7 C12 C13 5.5(3) . . . . ?
S1 N1 C13 C14 162.77(15) . . . . ?
S1 N1 C13 C12 35.4(2) . . . . ?
C11 C12 C13 N1 112.0(2) . . . . ?
C7 C12 C13 N1 -72.7(3) . . . . ?
C11 C12 C13 C14 -10.6(3) . . . . ?
C7 C12 C13 C14 164.7(2) . . . . ?
N1 C13 C14 C15 135.1(2) . . . . ?
C12 C13 C14 C15 -98.3(3) . . . . ?
N1 C13 C14 C19 -42.4(3) . . . . ?
C12 C13 C14 C19 84.3(3) . . . . ?
C19 C14 C15 C16 -0.3(4) . . . . ?
C13 C14 C15 C16 -177.8(2) . . . . ?
C14 C15 C16 C17 -0.4(5) . . . . ?
C15 C16 C17 C18 0.3(5) . . . . ?
C16 C17 C18 C19 0.6(6) . . . . ?
C17 C18 C19 C14 -1.3(5) . . . . ?
C15 C14 C19 C18 1.2(4) . . . . ?
C13 C14 C19 C18 178.6(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.93(3) 2.17(3) 2.946(3) 140(2) 2_546
C13 H13 O1 0.98 2.66 3.165(3) 112.4 2_546

_refine_diff_density_max         0.171
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.028

_shelxl_version_number           2013-4



