# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_OPTZ
_audit_block_doi                 10.5517/ccdc.csd.cc2f1qbk
_database_code_depnum_ccdc_archive 'CCDC 2235978'
loop_
_audit_author_name
_audit_author_address
'Wang Yunsheng'
;Tianjin University
China
;
_audit_update_record             
;
2023-01-13 deposited with the CCDC.	2023-01-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H12 N2 O2 S'
_chemical_formula_weight         332.37

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2330(16)
_cell_length_b                   8.8726(17)
_cell_length_c                   12.131(2)
_cell_angle_alpha                95.547(3)
_cell_angle_beta                 96.437(3)
_cell_angle_gamma                114.746(2)
_cell_volume                     789.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    57
_cell_measurement_theta_min      7.5
_cell_measurement_theta_max      20

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             344
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9394
_exptl_absorpt_correction_T_max  0.9515
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  bruker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5808
_diffrn_reflns_av_R_equivalents  0.0136
_diffrn_reflns_av_sigmaI/netI    0.0279
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         28.25
_reflns_number_total             3875
_reflns_number_gt                2896
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0382P)²+0.3732P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0033(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3875
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1120
_refine_ls_wR_factor_gt          0.1005
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      0.985
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0380(3) -0.3641(2) 0.16786(17) 0.0520(5) Uani 1 1 d . . .
H1 H -0.0091 -0.4717 0.1268 0.062 Uiso 1 1 calc R . .
C2 C -0.0754(3) -0.3052(3) 0.20998(19) 0.0595(5) Uani 1 1 d . . .
H2 H -0.2000 -0.3717 0.1972 0.071 Uiso 1 1 calc R . .
C3 C -0.0027(3) -0.1458(3) 0.27164(19) 0.0574(5) Uani 1 1 d . . .
H3 H -0.0793 -0.1068 0.3022 0.069 Uiso 1 1 calc R . .
C4 C 0.1806(3) -0.0433(2) 0.28894(17) 0.0496(4) Uani 1 1 d . . .
H4 H 0.2263 0.0634 0.3311 0.060 Uiso 1 1 calc R . .
C5 C 0.2980(2) -0.0982(2) 0.24382(14) 0.0393(4) Uani 1 1 d . . .
C6 C 0.2235(2) -0.2627(2) 0.18658(14) 0.0414(4) Uani 1 1 d . . .
C7 C 0.5846(2) -0.0127(2) 0.17121(14) 0.0406(4) Uani 1 1 d . . .
C8 C 0.7374(3) 0.1223(3) 0.15080(17) 0.0512(5) Uani 1 1 d . . .
H8 H 0.7785 0.2273 0.1946 0.061 Uiso 1 1 calc R . .
C9 C 0.8275(3) 0.1010(3) 0.06639(18) 0.0597(5) Uani 1 1 d . . .
H9 H 0.9292 0.1922 0.0537 0.072 Uiso 1 1 calc R . .
C10 C 0.7705(3) -0.0526(3) 0.00018(17) 0.0621(6) Uani 1 1 d . . .
H10 H 0.8309 -0.0639 -0.0582 0.075 Uiso 1 1 calc R . .
C11 C 0.6244(3) -0.1888(3) 0.02059(16) 0.0556(5) Uani 1 1 d . . .
H11 H 0.5860 -0.2935 -0.0231 0.067 Uiso 1 1 calc R . .
C12 C 0.5342(2) -0.1694(2) 0.10686(15) 0.0439(4) Uani 1 1 d . . .
C13 C 0.5653(2) 0.1588(2) 0.33397(14) 0.0393(4) Uani 1 1 d . . .
C14 C 0.6691(3) 0.1577(2) 0.43080(15) 0.0463(4) Uani 1 1 d . . .
H14 H 0.6818 0.0608 0.4423 0.056 Uiso 1 1 calc R . .
C15 C 0.7544(3) 0.3004(2) 0.51092(16) 0.0502(4) Uani 1 1 d . . .
H15 H 0.8253 0.3005 0.5762 0.060 Uiso 1 1 calc R . .
C16 C 0.7333(2) 0.4432(2) 0.49309(16) 0.0458(4) Uani 1 1 d . . .
C17 C 0.6279(3) 0.4437(2) 0.39633(17) 0.0514(5) Uani 1 1 d . . .
H17 H 0.6134 0.5399 0.3852 0.062 Uiso 1 1 calc R . .
C18 C 0.5444(3) 0.3015(2) 0.31635(16) 0.0495(4) Uani 1 1 d . . .
H18 H 0.4742 0.3015 0.2507 0.059 Uiso 1 1 calc R . .
C19 C 0.8233(3) 0.5929(3) 0.5753(2) 0.0613(6) Uani 1 1 d . . .
N1 N 0.48299(19) 0.00831(17) 0.25156(12) 0.0420(3) Uani 1 1 d . . .
N2 N 0.8956(3) 0.7127(3) 0.6387(2) 0.0952(8) Uani 1 1 d . . .
O1 O 0.4503(2) -0.3821(2) 0.24328(15) 0.0762(5) Uani 1 1 d . . .
O2 O 0.2793(2) -0.4764(2) 0.05199(16) 0.0853(6) Uani 1 1 d . . .
S1 S 0.36914(7) -0.34413(6) 0.14590(4) 0.05230(16) 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 C2 1.367(3) . ?
C1 C6 1.388(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.380(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(2) . ?
C5 N1 1.402(2) . ?
C6 S1 1.7298(18) . ?
C7 C8 1.394(3) . ?
C7 C12 1.397(2) . ?
C7 N1 1.401(2) . ?
C8 C9 1.373(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.375(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.370(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.387(3) . ?
C11 H11 0.9300 . ?
C12 S1 1.731(2) . ?
C13 C14 1.376(2) . ?
C13 C18 1.380(2) . ?
C13 N1 1.440(2) . ?
C14 C15 1.380(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.382(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.381(3) . ?
C16 C19 1.436(3) . ?
C17 C18 1.376(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 N2 1.134(3) . ?
O1 S1 1.4297(16) . ?
O2 S1 1.4314(16) . ?

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
C2 C1 C6 119.76(18) . . ?
C2 C1 H1 120.1 . . ?
C6 C1 H1 120.1 . . ?
C1 C2 C3 119.21(18) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C4 C3 C2 121.43(19) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 120.47(18) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 117.32(16) . . ?
C4 C5 N1 121.78(15) . . ?
C6 C5 N1 120.86(15) . . ?
C1 C6 C5 121.65(17) . . ?
C1 C6 S1 119.78(14) . . ?
C5 C6 S1 118.45(13) . . ?
C8 C7 C12 117.49(16) . . ?
C8 C7 N1 121.43(16) . . ?
C12 C7 N1 121.07(16) . . ?
C9 C8 C7 120.34(19) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 121.3(2) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 H9 119.3 . . ?
C11 C10 C9 119.68(19) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 119.5(2) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C11 C12 C7 121.55(19) . . ?
C11 C12 S1 120.03(15) . . ?
C7 C12 S1 118.14(14) . . ?
C14 C13 C18 120.49(16) . . ?
C14 C13 N1 118.01(15) . . ?
C18 C13 N1 121.49(16) . . ?
C13 C14 C15 120.07(17) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 119.34(17) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C17 C16 C15 120.57(17) . . ?
C17 C16 C19 119.65(18) . . ?
C15 C16 C19 119.77(18) . . ?
C16 C17 C18 119.81(17) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C13 C18 C17 119.72(17) . . ?
C13 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
N2 C19 C16 178.8(3) . . ?
C7 N1 C5 122.06(14) . . ?
C7 N1 C13 117.99(14) . . ?
C5 N1 C13 119.24(13) . . ?
O1 S1 O2 117.36(11) . . ?
O1 S1 C6 108.33(10) . . ?
O2 S1 C6 110.46(9) . . ?
O1 S1 C12 107.71(9) . . ?
O2 S1 C12 110.96(10) . . ?
C6 S1 C12 100.68(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
C6 C1 C2 C3 -0.7(3) . . . . ?
C1 C2 C3 C4 1.8(3) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 C6 -3.5(3) . . . . ?
C3 C4 C5 N1 174.31(18) . . . . ?
C2 C1 C6 C5 -2.7(3) . . . . ?
C2 C1 C6 S1 173.42(16) . . . . ?
C4 C5 C6 C1 4.7(3) . . . . ?
N1 C5 C6 C1 -173.13(17) . . . . ?
C4 C5 C6 S1 -171.45(14) . . . . ?
N1 C5 C6 S1 10.7(2) . . . . ?
C12 C7 C8 C9 3.2(3) . . . . ?
N1 C7 C8 C9 -175.53(17) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C8 C9 C10 C11 -2.1(3) . . . . ?
C9 C10 C11 C12 0.9(3) . . . . ?
C10 C11 C12 C7 2.3(3) . . . . ?
C10 C11 C12 S1 -171.46(15) . . . . ?
C8 C7 C12 C11 -4.4(3) . . . . ?
N1 C7 C12 C11 174.38(16) . . . . ?
C8 C7 C12 S1 169.55(13) . . . . ?
N1 C7 C12 S1 -11.7(2) . . . . ?
C18 C13 C14 C15 -0.4(3) . . . . ?
N1 C13 C14 C15 178.37(16) . . . . ?
C13 C14 C15 C16 0.4(3) . . . . ?
C14 C15 C16 C17 0.1(3) . . . . ?
C14 C15 C16 C19 -179.22(18) . . . . ?
C15 C16 C17 C18 -0.6(3) . . . . ?
C19 C16 C17 C18 178.70(19) . . . . ?
C14 C13 C18 C17 -0.1(3) . . . . ?
N1 C13 C18 C17 -178.85(17) . . . . ?
C16 C17 C18 C13 0.6(3) . . . . ?
C17 C16 C19 N2 -51(11) . . . . ?
C15 C16 C19 N2 128(11) . . . . ?
C8 C7 N1 C5 153.24(17) . . . . ?
C12 C7 N1 C5 -25.4(2) . . . . ?
C8 C7 N1 C13 -17.1(2) . . . . ?
C12 C7 N1 C13 164.27(15) . . . . ?
C4 C5 N1 C7 -151.73(17) . . . . ?
C6 C5 N1 C7 26.0(2) . . . . ?
C4 C5 N1 C13 18.4(2) . . . . ?
C6 C5 N1 C13 -163.84(15) . . . . ?
C14 C13 N1 C7 -87.3(2) . . . . ?
C18 C13 N1 C7 91.5(2) . . . . ?
C14 C13 N1 C5 102.10(19) . . . . ?
C18 C13 N1 C5 -79.1(2) . . . . ?
C1 C6 S1 O1 -101.47(17) . . . . ?
C5 C6 S1 O1 74.74(16) . . . . ?
C1 C6 S1 O2 28.35(19) . . . . ?
C5 C6 S1 O2 -155.44(15) . . . . ?
C1 C6 S1 C12 145.67(15) . . . . ?
C5 C6 S1 C12 -38.12(16) . . . . ?
C11 C12 S1 O1 99.21(16) . . . . ?
C7 C12 S1 O1 -74.79(16) . . . . ?
C11 C12 S1 O2 -30.50(18) . . . . ?
C7 C12 S1 O2 155.50(14) . . . . ?
C11 C12 S1 C6 -147.45(15) . . . . ?
C7 C12 S1 C6 38.55(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        28.25
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.041
####################################################################### 
# 
# 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_cs-phcn-czs-phcn
_database_code_depnum_ccdc_archive 'CCDC 2216776'
loop_
_audit_author_name
_audit_author_address
'Yang Jie'
;Tianjin University
China
;
_audit_update_record             
;
2022-11-01 deposited with the CCDC.	2023-01-24 downloaded from the CCDC.
;
_audit_creation_date             2020-07-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H12 N2 O2 S'
_chemical_formula_sum            'C19 H12 N2 O2 S'
_chemical_formula_weight         332.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N S'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.2579(4)
_cell_length_b                   8.8946(4)
_cell_length_c                   12.1498(5)
_cell_angle_alpha                95.502(3)
_cell_angle_beta                 96.531(4)
_cell_angle_gamma                114.779(4)
_cell_volume                     794.73(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8374
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.0560
_cell_measurement_theta_min      5.5230
_shelx_estimated_absorpt_T_max   0.846
_shelx_estimated_absorpt_T_min   0.736
_exptl_absorpt_coefficient_mu    1.923
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12039
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.062
_diffrn_reflns_theta_max         67.062
_diffrn_reflns_theta_min         3.709
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1975
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      0.00  25.00   1.00    1.05    --   38.00  93.00-120.38   25
  2  ω    -63.00  32.00   1.00    1.05    --  -41.12  37.00 120.00   95
  3  ω   -116.00 -57.00   1.00    1.05    --  -41.12 -37.00 -30.00   59
  4  ω   -109.00 -73.00   1.00    1.05    --  -41.12 -61.00 104.00   36
  5  ω    -62.00 -14.00   1.00    1.05    --  -41.12 -57.00-180.00   48
  6  ω    -56.00 -17.00   1.00    1.05    --  -41.12 -37.00 -30.00   39
  7  ω    -68.00 -13.00   1.00    1.05    --  -41.12 -61.00 104.00   55
  8  ω    -14.00  56.00   1.00    1.05    --   41.12 -77.00 -30.00   70
  9  ω     23.00  96.00   1.00    1.05    --   41.12-125.00-150.00   73
 10  ω      5.00  30.00   1.00    1.05    --   42.00  89.00 -51.79   25
 11  ω     11.00  36.00   1.00    1.05    --   46.00  84.00  53.57   25
 12  ω     11.00  36.00   1.00    1.05    --   46.00  84.00 122.06   25
 13  ω     16.00  41.00   1.00    1.05    --   50.00  82.00-144.94   25
 14  ω     93.00 133.00   1.00    1.05    --   58.00  74.00  23.27   40
 15  ω     33.00  63.00   1.00    1.05    --   58.00  74.00  23.27   30
 16  ω     25.00  51.00   1.00    1.05    --   58.00  77.00-101.48   26
 17  ω     35.00  70.00   1.00    1.05    --   62.00  77.00 113.32   35
 18  ω     74.00 130.00   1.00    1.05    --   62.00  77.00 -76.36   56
 19  ω     32.00  58.00   1.00    1.05    --   62.00  77.00 -76.36   26
 20  ω     30.00  90.00   1.00    1.05    --   62.00  77.00 -38.02   60
 21  ω     37.00  90.00   1.00    1.05    --   66.00  77.00-170.77   53
 22  ω    104.00 142.00   1.00    1.05    --   66.00  77.00  61.16   38
 23  ω     33.00  70.00   1.00    1.05    --   66.00  77.00  61.16   37
 24  ω     36.00  62.00   1.00    1.05    --   66.00  77.00 157.53   26
 25  ω     74.00 178.00   1.00    4.18    --  105.32  77.00   0.00  104
 26  ω     75.00 176.00   1.00    4.18    --  105.32  77.00 -60.00  101
 27  ω    124.00 178.00   1.00    4.18    --  105.32  77.00 150.00   54
 28  ω     23.00 109.00   1.00    4.18    --  105.32 -94.00 -30.00   86
 29  ω     73.00 104.00   1.00    4.18    --  105.32  77.00 150.00   31
 30  ω     73.00 172.00   1.00    4.18    --  105.32  77.00 120.00   99
 31  ω     78.00 103.00   1.00    4.18    --  105.32  61.00  30.00   25
 32  ω    114.00 140.00   1.00    4.18    --  105.32  77.00  30.00   26
 33  ω     78.00 114.00   1.00    4.18    --  105.32  61.00   0.00   36
 34  ω     75.00 109.00   1.00    4.18    --  105.32  77.00  30.00   34
 35  ω     74.00  99.00   1.00    4.18    --  105.32  77.00 -90.00   25
 36  ω    135.00 174.00   1.00    4.18    --  105.32  77.00-120.00   39
 37  ω    105.00 174.00   1.00    4.18    --  105.32  77.00-150.00   69
 38  ω     76.00 102.00   1.00    4.18    --  105.32  77.00-120.00   26
 39  ω     75.00 101.00   1.00    4.18    --  105.32  77.00-150.00   26
 40  ω    126.00 162.00   1.00    4.18    --  105.32 125.00  30.00   36
 41  ω    120.00 148.00   1.00    4.18    --  105.32  77.00 -30.00   28
 42  ω     82.00 159.00   1.00    4.18    --  105.32  61.00-180.00   77
 43  ω     73.00  99.00   1.00    4.18    --  105.32  77.00 -30.00   26
 44  ω    131.00 157.00   1.00    4.18    --  105.32  61.00  90.00   26
 45  ω     77.00 108.00   1.00    4.18    --  105.32  61.00  90.00   31
 46  ω     81.00 114.00   1.00    4.18    --  105.32  61.00 120.00   33
 47  ω     77.00 105.00   1.00    4.18    --  105.32  61.00 -60.00   28
 48  ω     77.00 102.00   1.00    4.18    --  105.32  61.00-117.00   25
 49  ω     73.00 104.00   1.00    4.18    --  105.32 -94.00-150.00   31
 50  ω     73.00 164.00   1.00    4.18    --  105.32  77.00  60.00   91
 51  ω     46.00 133.00   1.00    4.18    --  105.32 -77.00  30.00   87
 52  ω     80.00 107.00   1.00    4.18    --  105.32  61.00 150.00   27
 53  ω     51.00 117.00   1.00    4.18    --  105.32-125.00-120.00   66
 54  ω     80.00 164.00   1.00    4.18    --  105.32  61.00 -90.00   84
 55  ω     76.00 102.00   1.00    4.18    --  105.32  61.00-150.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0171782000
_diffrn_orient_matrix_UB_12      -0.1102269000
_diffrn_orient_matrix_UB_13      0.0924309000
_diffrn_orient_matrix_UB_21      0.1862060000
_diffrn_orient_matrix_UB_22      0.0053266000
_diffrn_orient_matrix_UB_23      -0.0112507000
_diffrn_orient_matrix_UB_31      0.0922693000
_diffrn_orient_matrix_UB_32      0.1586149000
_diffrn_orient_matrix_UB_33      0.0896739000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2684
_reflns_number_total             2829
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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         0.263
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0097(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2829
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0335
_refine_ls_restrained_S_all      1.071
_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)+(0.0493P)²+0.1558P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.0935
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12),
 C14(H14), C15(H15), C17(H17), C18(H18)
;
_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 0.36903(5) 0.15539(5) 0.14598(3) 0.05556(16) Uani 1 1 d . . . . .
O1 O 0.2796(2) 0.02400(18) 0.05203(14) 0.0925(5) Uani 1 1 d . . . . .
O2 O 0.45008(19) 0.11791(18) 0.24353(13) 0.0825(4) Uani 1 1 d . . . . .
N1 N 0.48284(16) 0.50807(15) 0.25152(10) 0.0462(3) Uani 1 1 d . . . . .
N2 N 0.8952(3) 1.2125(3) 0.63883(19) 0.1013(7) Uani 1 1 d . . . . .
C1 C 0.1805(2) 0.4567(2) 0.28873(13) 0.0530(4) Uani 1 1 d . . . . .
H1 H 0.2261 0.5633 0.3307 0.064 Uiso 1 1 calc R . . . .
C2 C -0.0026(2) 0.3540(2) 0.27130(15) 0.0611(4) Uani 1 1 d . . . . .
H2 H -0.0790 0.3928 0.3016 0.073 Uiso 1 1 calc R . . . .
C3 C -0.0755(2) 0.1943(2) 0.20980(15) 0.0629(4) Uani 1 1 d . . . . .
H3 H -0.1998 0.1278 0.1970 0.076 Uiso 1 1 calc R . . . .
C4 C 0.0379(2) 0.1355(2) 0.16799(13) 0.0561(4) Uani 1 1 d . . . . .
H4 H -0.0090 0.0279 0.1273 0.067 Uiso 1 1 calc R . . . .
C5 C 0.22311(19) 0.23694(17) 0.18654(11) 0.0452(3) Uani 1 1 d . . . . .
C6 C 0.29821(18) 0.40163(17) 0.24361(11) 0.0427(3) Uani 1 1 d . . . . .
C7 C 0.58468(18) 0.48716(18) 0.17126(11) 0.0442(3) Uani 1 1 d . . . . .
C8 C 0.5340(2) 0.33013(19) 0.10700(11) 0.0477(3) Uani 1 1 d . . . . .
C9 C 0.6245(2) 0.3109(2) 0.02078(13) 0.0595(4) Uani 1 1 d . . . . .
H9 H 0.5864 0.2064 -0.0227 0.071 Uiso 1 1 calc R . . . .
C10 C 0.7702(2) 0.4469(3) 0.00033(14) 0.0661(5) Uani 1 1 d . . . . .
H10 H 0.8303 0.4355 -0.0579 0.079 Uiso 1 1 calc R . . . .
C11 C 0.8272(2) 0.6008(2) 0.06655(15) 0.0632(4) Uani 1 1 d . . . . .
H11 H 0.9286 0.6920 0.0540 0.076 Uiso 1 1 calc R . . . .
C12 C 0.7369(2) 0.6218(2) 0.15063(14) 0.0550(4) Uani 1 1 d . . . . .
H12 H 0.7777 0.7267 0.1942 0.066 Uiso 1 1 calc R . . . .
C13 C 0.56528(18) 0.65852(17) 0.33385(11) 0.0428(3) Uani 1 1 d . . . . .
C14 C 0.5438(2) 0.80087(19) 0.31613(13) 0.0532(4) Uani 1 1 d . . . . .
H14 H 0.4732 0.8005 0.2506 0.064 Uiso 1 1 calc R . . . .
C15 C 0.6273(2) 0.94332(19) 0.39590(14) 0.0557(4) Uani 1 1 d . . . . .
H15 H 0.6128 1.0392 0.3847 0.067 Uiso 1 1 calc R . . . .
C16 C 0.73291(19) 0.94272(19) 0.49288(12) 0.0494(3) Uani 1 1 d . . . . .
C17 C 0.7544(2) 0.8003(2) 0.51073(12) 0.0535(4) Uani 1 1 d . . . . .
H17 H 0.8254 0.8006 0.5760 0.064 Uiso 1 1 calc R . . . .
C18 C 0.6695(2) 0.65792(18) 0.43092(12) 0.0496(3) Uani 1 1 d . . . . .
H18 H 0.6825 0.5614 0.4425 0.059 Uiso 1 1 calc R . . . .
C19 C 0.8230(2) 1.0929(2) 0.57525(16) 0.0659(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4293(13) . ?
S1 O2 1.4305(14) . ?
S1 C5 1.7379(14) . ?
S1 C8 1.7346(16) . ?
N1 C6 1.4033(18) . ?
N1 C7 1.4056(18) . ?
N1 C13 1.4421(17) . ?
N2 C19 1.136(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.378(2) . ?
C1 C6 1.398(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.384(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.369(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.390(2) . ?
C5 C6 1.3989(19) . ?
C7 C8 1.401(2) . ?
C7 C12 1.395(2) . ?
C8 C9 1.392(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.370(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.381(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.374(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.383(2) . ?
C13 C18 1.381(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.379(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.386(2) . ?
C16 C17 1.384(2) . ?
C16 C19 1.443(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.379(2) . ?
C18 H18 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 117.69(10) . . ?
O1 S1 C5 110.42(8) . . ?
O1 S1 C8 110.78(9) . . ?
O2 S1 C5 108.23(8) . . ?
O2 S1 C8 107.66(8) . . ?
C8 S1 C5 100.68(7) . . ?
C6 N1 C7 122.08(11) . . ?
C6 N1 C13 119.34(11) . . ?
C7 N1 C13 117.87(11) . . ?
C2 C1 H1 119.8 . . ?
C2 C1 C6 120.34(15) . . ?
C6 C1 H1 119.8 . . ?
C1 C2 H2 119.2 . . ?
C1 C2 C3 121.58(15) . . ?
C3 C2 H2 119.2 . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.13(15) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.82(15) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 S1 119.80(12) . . ?
C4 C5 C6 121.83(14) . . ?
C6 C5 S1 118.26(11) . . ?
C1 C6 N1 121.72(13) . . ?
C1 C6 C5 117.16(13) . . ?
C5 C6 N1 121.08(12) . . ?
C8 C7 N1 120.95(13) . . ?
C12 C7 N1 121.57(13) . . ?
C12 C7 C8 117.47(13) . . ?
C7 C8 S1 118.24(11) . . ?
C9 C8 S1 120.08(13) . . ?
C9 C8 C7 121.39(15) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.59(16) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.66(15) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.19(17) . . ?
C12 C11 H11 119.4 . . ?
C7 C12 H12 119.7 . . ?
C11 C12 C7 120.57(16) . . ?
C11 C12 H12 119.7 . . ?
C14 C13 N1 121.41(12) . . ?
C18 C13 N1 118.08(12) . . ?
C18 C13 C14 120.50(13) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.76(14) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 120.2 . . ?
C14 C15 C16 119.61(14) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 C19 119.51(15) . . ?
C17 C16 C15 120.67(13) . . ?
C17 C16 C19 119.82(15) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 C16 119.41(14) . . ?
C18 C17 H17 120.3 . . ?
C13 C18 H18 120.0 . . ?
C17 C18 C13 120.04(13) . . ?
C17 C18 H18 120.0 . . ?
N2 C19 C16 178.9(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.345
_oxdiff_exptl_absorpt_empirical_full_min 0.778
####################################################################### 
# 
# 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_161226d_0m
_database_code_depnum_ccdc_archive 'CCDC 2216826'
loop_
_audit_author_name
_audit_author_address
'Yang Jie'
;Tianjin University
China
;
_audit_update_record             
;
2022-11-01 deposited with the CCDC.	2023-01-24 downloaded from the CCDC.
;
_audit_creation_date             2022-11-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H12 N2 S'
_chemical_formula_sum            'C19 H12 N2 S'
_chemical_formula_weight         300.37
_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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   10.3472(10)
_cell_length_b                   12.6805(12)
_cell_length_c                   12.7346(12)
_cell_angle_alpha                91.2810(14)
_cell_angle_beta                 109.3896(14)
_cell_angle_gamma                111.0594(13)
_cell_volume                     1451.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8374
_cell_measurement_temperature    298
_cell_measurement_theta_max      73.0560
_cell_measurement_theta_min      5.5230
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13260
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.72
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD diffractometer'
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                4603
_reflns_number_total             5065
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         5065
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0332
_refine_ls_restrained_S_all      1.116
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0719P)²+0.6247P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1183
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C13(H13), C14(H14), C16(H16), C20(H20), C21(H21), C22(H22), C25(H25),
 C29(H29), C31(H31), C36(H36), C41(H41), C7(H7), C19(H19), C26(H26), C30(H30),
 C32(H32), C33(H33), C35(H35), C37(H37), C38(H38), C39(H39), C40(H40), C42(H42)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.75577(5) 0.17535(4) 0.02884(4) 0.01905(14) Uani 1 d . . .
N3 N 0.61690(16) 0.27506(12) -0.16691(12) 0.0180(3) Uani 1 d . . .
C3 C 0.68125(19) 0.39477(14) -0.15715(14) 0.0174(4) Uani 1 d . . .
C4 C 0.76514(19) 0.15933(14) -0.10663(14) 0.0172(4) Uani 1 d . . .
C6 C 0.57476(19) 0.17515(14) -0.01255(14) 0.0181(4) Uani 1 d . . .
C8 C 0.8814(2) 0.56524(15) -0.16254(15) 0.0209(4) Uani 1 d . . .
H8 H 0.9736 0.5996 -0.1693 0.025 Uiso 1 calc . . R
C9 C 0.69250(19) 0.20798(14) -0.19155(15) 0.0172(4) Uani 1 d . . .
C10 C 0.52152(19) 0.22389(14) -0.10644(15) 0.0177(4) Uani 1 d . . .
N4 N 0.91503(17) 0.85236(13) -0.14329(14) 0.0245(4) Uani 1 d . . .
C13 C 0.3781(2) 0.22099(15) -0.13957(16) 0.0220(4) Uani 1 d . . .
H13 H 0.3392 0.2480 -0.2052 0.026 Uiso 1 calc . . R
C14 C 0.6938(2) 0.19168(14) -0.29949(15) 0.0192(4) Uani 1 d . . .
H14 H 0.6424 0.2218 -0.3570 0.023 Uiso 1 calc . . R
C16 C 0.6693(2) 0.58044(15) -0.13502(14) 0.0192(4) Uani 1 d . . .
H16 H 0.6187 0.6248 -0.1242 0.023 Uiso 1 calc . . R
C20 C 0.6082(2) 0.46369(15) -0.13889(15) 0.0198(4) Uani 1 d . . .
H20 H 0.5177 0.4302 -0.1293 0.024 Uiso 1 calc . . R
C21 C 0.4871(2) 0.12861(14) 0.05023(15) 0.0216(4) Uani 1 d . . .
H21 H 0.5214 0.0944 0.1115 0.026 Uiso 1 calc . . R
C22 C 0.8203(2) 0.44820(15) -0.16769(15) 0.0202(4) Uani 1 d . . .
H22 H 0.8714 0.4042 -0.1782 0.024 Uiso 1 calc . . R
C25 C 0.84290(19) 0.09715(14) -0.12864(15) 0.0186(4) Uani 1 d . . .
H25 H 0.8917 0.0648 -0.0719 0.022 Uiso 1 calc . . R
C27 C 0.8058(2) 0.63280(15) -0.14715(14) 0.0187(4) Uani 1 d . . .
C29 C 0.7719(2) 0.13030(15) -0.32103(15) 0.0210(4) Uani 1 d . . .
H29 H 0.7740 0.1203 -0.3929 0.025 Uiso 1 calc . . R
C31 C 0.8470(2) 0.08384(14) -0.23601(15) 0.0201(4) Uani 1 d . . .
H31 H 0.9002 0.0436 -0.2508 0.024 Uiso 1 calc . . R
C34 C 0.86753(19) 0.75472(15) -0.14487(15) 0.0196(4) Uani 1 d . . .
C36 C 0.3477(2) 0.13358(15) 0.02076(17) 0.0253(4) Uani 1 d . . .
H36 H 0.2912 0.1071 0.0654 0.030 Uiso 1 calc . . R
C41 C 0.2927(2) 0.17768(15) -0.07442(17) 0.0252(4) Uani 1 d . . .
H41 H 0.1980 0.1784 -0.0950 0.030 Uiso 1 calc . . R
S2 S 0.19754(5) 0.50411(4) 0.46554(4) 0.02127(14) Uani 1 d . . .
N1 N 0.35584(16) 0.69447(12) 0.66096(12) 0.0180(3) Uani 1 d . . .
C5 C 0.3812(2) 0.60577(15) 0.50099(15) 0.0191(4) Uani 1 d . . .
C7 C 0.16827(19) 0.76150(15) 0.67576(14) 0.0187(4) Uani 1 d . . .
H7 H 0.1185 0.6910 0.6930 0.022 Uiso 1 calc . . R
C12 C 0.29941(19) 0.78102(14) 0.65592(14) 0.0163(4) Uani 1 d . . .
C15 C 0.27844(19) 0.58606(14) 0.68786(15) 0.0175(4) Uani 1 d . . .
C17 C 0.19835(19) 0.49057(15) 0.60364(15) 0.0178(4) Uani 1 d . . .
C18 C 0.1214(2) 1.03754(15) 0.63274(15) 0.0214(4) Uani 1 d . . .
C19 C 0.2836(2) 0.57573(15) 0.79733(15) 0.0205(4) Uani 1 d . . .
H19 H 0.3399 0.6388 0.8544 0.025 Uiso 1 calc . . R
N2 N 0.07159(19) 1.10612(14) 0.62112(14) 0.0273(4) Uani 1 d . . .
C24 C 0.4435(2) 0.69124(15) 0.59494(15) 0.0182(4) Uani 1 d . . .
C26 C 0.1215(2) 0.38509(15) 0.62843(16) 0.0207(4) Uani 1 d . . .
H26 H 0.0691 0.3211 0.5723 0.025 Uiso 1 calc . . R
C28 C 0.1839(2) 0.95171(15) 0.64478(14) 0.0193(4) Uani 1 d . . .
C30 C 0.2045(2) 0.47106(15) 0.82155(16) 0.0220(4) Uani 1 d . . .
H30 H 0.2059 0.4647 0.8945 0.026 Uiso 1 calc . . R
C32 C 0.1116(2) 0.84544(16) 0.67013(15) 0.0217(4) Uani 1 d . . .
H32 H 0.0241 0.8308 0.6834 0.026 Uiso 1 calc . . R
C33 C 0.3729(2) 0.88884(15) 0.63236(15) 0.0207(4) Uani 1 d . . .
H33 H 0.4611 0.9042 0.6200 0.025 Uiso 1 calc . . R
C35 C 0.3160(2) 0.97287(15) 0.62719(15) 0.0212(4) Uani 1 d . . .
H35 H 0.3666 1.0441 0.6118 0.025 Uiso 1 calc . . R
C37 C 0.4636(2) 0.60061(16) 0.43523(16) 0.0236(4) Uani 1 d . . .
H37 H 0.4242 0.5413 0.3751 0.028 Uiso 1 calc . . R
C38 C 0.5890(2) 0.77009(16) 0.62358(16) 0.0227(4) Uani 1 d . . .
H38 H 0.6337 0.8238 0.6891 0.027 Uiso 1 calc . . R
C39 C 0.1235(2) 0.37603(15) 0.73721(16) 0.0222(4) Uani 1 d . . .
H39 H 0.0705 0.3062 0.7537 0.027 Uiso 1 calc . . R
C40 C 0.6042(2) 0.68413(18) 0.46001(17) 0.0277(4) Uani 1 d . . .
H40 H 0.6570 0.6839 0.4135 0.033 Uiso 1 calc . . R
C42 C 0.6669(2) 0.76823(17) 0.55409(17) 0.0275(4) Uani 1 d . . .
H42 H 0.7619 0.8238 0.5707 0.033 Uiso 1 calc . . R


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C4 1.7710(17) . ?
S1 C6 1.7682(18) . ?
N3 C3 1.405(2) . ?
N3 C9 1.436(2) . ?
N3 C10 1.433(2) . ?
C3 C20 1.404(2) . ?
C3 C22 1.407(3) . ?
C4 C9 1.392(2) . ?
C4 C25 1.394(2) . ?
C6 C10 1.398(3) . ?
C6 C21 1.389(3) . ?
C8 C22 1.379(3) . ?
C8 C27 1.400(2) . ?
C9 C14 1.391(2) . ?
C10 C13 1.388(3) . ?
N4 C34 1.153(2) . ?
C13 C41 1.389(3) . ?
C14 C29 1.388(3) . ?
C16 C20 1.377(2) . ?
C16 C27 1.392(3) . ?
C21 C36 1.390(3) . ?
C25 C31 1.390(2) . ?
C27 C34 1.441(2) . ?
C29 C31 1.386(3) . ?
C36 C41 1.381(3) . ?
S2 C5 1.7664(19) . ?
S2 C17 1.7683(18) . ?
N1 C12 1.410(2) . ?
N1 C15 1.435(2) . ?
N1 C24 1.436(2) . ?
C5 C24 1.396(3) . ?
C5 C37 1.395(3) . ?
C7 C12 1.398(2) . ?
C7 C32 1.380(3) . ?
C12 C33 1.400(2) . ?
C15 C17 1.391(2) . ?
C15 C19 1.388(2) . ?
C17 C26 1.394(3) . ?
C18 N2 1.149(2) . ?
C18 C28 1.440(2) . ?
C19 C30 1.390(3) . ?
C24 C38 1.392(3) . ?
C26 C39 1.387(3) . ?
C28 C32 1.391(3) . ?
C28 C35 1.390(3) . ?
C30 C39 1.388(3) . ?
C33 C35 1.384(3) . ?
C37 C40 1.382(3) . ?
C38 C42 1.385(3) . ?
C40 C42 1.387(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 S1 C4 98.57(8) . . ?
C3 N3 C9 119.13(14) . . ?
C3 N3 C10 119.99(13) . . ?
C10 N3 C9 115.11(13) . . ?
N3 C3 C22 120.27(15) . . ?
C20 C3 N3 121.32(15) . . ?
C20 C3 C22 118.40(15) . . ?
C9 C4 S1 119.50(13) . . ?
C9 C4 C25 120.17(16) . . ?
C25 C4 S1 120.32(14) . . ?
C10 C6 S1 120.19(13) . . ?
C21 C6 S1 119.59(14) . . ?
C21 C6 C10 120.20(17) . . ?
C22 C8 C27 120.53(16) . . ?
C4 C9 N3 119.68(15) . . ?
C14 C9 N3 120.39(16) . . ?
C14 C9 C4 119.93(16) . . ?
C6 C10 N3 118.82(15) . . ?
C13 C10 N3 121.53(16) . . ?
C13 C10 C6 119.65(16) . . ?
C10 C13 C41 119.78(18) . . ?
C29 C14 C9 119.75(17) . . ?
C20 C16 C27 120.72(16) . . ?
C16 C20 C3 120.68(16) . . ?
C6 C21 C36 119.47(18) . . ?
C8 C22 C3 120.55(16) . . ?
C31 C25 C4 119.52(16) . . ?
C8 C27 C34 120.64(16) . . ?
C16 C27 C8 119.08(16) . . ?
C16 C27 C34 120.28(15) . . ?
C31 C29 C14 120.39(16) . . ?
C29 C31 C25 120.20(16) . . ?
N4 C34 C27 179.07(18) . . ?
C41 C36 C21 120.33(17) . . ?
C36 C41 C13 120.32(18) . . ?
C5 S2 C17 98.42(8) . . ?
C12 N1 C15 119.50(14) . . ?
C12 N1 C24 119.91(14) . . ?
C15 N1 C24 115.09(13) . . ?
C24 C5 S2 119.83(13) . . ?
C37 C5 S2 120.04(14) . . ?
C37 C5 C24 120.13(17) . . ?
C32 C7 C12 120.89(16) . . ?
C7 C12 N1 120.51(15) . . ?
C7 C12 C33 118.04(15) . . ?
C33 C12 N1 121.45(15) . . ?
C17 C15 N1 119.68(15) . . ?
C19 C15 N1 120.52(15) . . ?
C19 C15 C17 119.80(16) . . ?
C15 C17 S2 119.27(13) . . ?
C15 C17 C26 120.23(16) . . ?
C26 C17 S2 120.49(13) . . ?
N2 C18 C28 178.72(19) . . ?
C15 C19 C30 119.93(16) . . ?
C5 C24 N1 118.88(16) . . ?
C38 C24 N1 121.48(16) . . ?
C38 C24 C5 119.63(16) . . ?
C39 C26 C17 119.70(16) . . ?
C32 C28 C18 121.09(17) . . ?
C35 C28 C18 120.03(16) . . ?
C35 C28 C32 118.85(16) . . ?
C39 C30 C19 120.20(17) . . ?
C7 C32 C28 120.75(17) . . ?
C35 C33 C12 120.87(16) . . ?
C33 C35 C28 120.58(17) . . ?
C40 C37 C5 119.61(18) . . ?
C42 C38 C24 119.70(18) . . ?
C26 C39 C30 120.09(16) . . ?
C37 C40 C42 120.19(17) . . ?
C38 C42 C40 120.48(18) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
