# Supplementary Information (SI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2025

####################################################################### 
# 
# 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_SSS16_a
_database_code_depnum_ccdc_archive 'CCDC 2443161'
loop_
_audit_author_name
_audit_author_address
'Souvik Santra'
;University of Calcutta 
India
;
_audit_update_record             
;
2025-04-11 deposited with the CCDC.	2025-09-29 downloaded from the CCDC.
;
_audit_creation_date             2024-02-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_chemical_formula_moiety         'C12 H9 N3 O'
_chemical_formula_sum            'C12 H9 N3 O'
_chemical_formula_weight         211.225
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00313 0.00162 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.01085 0.00610 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   12.478(3)
_cell_length_b                   6.1791(18)
_cell_length_c                   13.853(3)
_cell_angle_alpha                90
_cell_angle_beta                 113.521(8)
_cell_angle_gamma                90
_cell_volume                     979.3(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4406
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      33.60
_cell_measurement_theta_min      3.67
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7468
_exptl_absorpt_correction_T_min  0.3749
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1674 before and 0.1211 after correction.
The Ratio of minimum to maximum transmission is 0.5020.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            transparent
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             440.290
_diffrn_reflns_av_R_equivalents  0.0964
_diffrn_reflns_av_unetI/netI     0.0987
_diffrn_reflns_Laue_measured_fraction_full 0.9938
_diffrn_reflns_Laue_measured_fraction_max 0.8688
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12561
_diffrn_reflns_point_group_measured_fraction_full 0.9938
_diffrn_reflns_point_group_measured_fraction_max 0.8688
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         34.47
_diffrn_reflns_theta_min         3.21
_diffrn_ambient_temperature      159.95
_diffrn_measured_fraction_theta_full 0.9938
_diffrn_measured_fraction_theta_max 0.8688
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              16
_reflns_limit_h_min              -19
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                2238
_reflns_number_total             3588
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.5133
_refine_diff_density_min         -0.5337
_refine_diff_density_rms         0.1379
_refine_ls_d_res_high            0.6279
_refine_ls_d_res_low             6.3510
_refine_ls_goodness_of_fit_ref   1.1664
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    14
_refine_ls_number_parameters     153
_refine_ls_number_reflns         3588
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1295
_refine_ls_R_factor_gt           0.0843
_refine_ls_restrained_S_all      1.1664
_refine_ls_shift/su_max          -0.0008
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1613P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2222
_refine_ls_wR_factor_ref         0.2976
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11), C10(H10), C2(H2a), C3(H3a), C5(H5), C4(H4)
;
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_refinement_flags_posn
O1 O 0.45309(11) 0.2520(2) 0.44464(12) 0.0393(4) Uani 1.000000 .
N2 N 0.34667(14) 0.5766(3) 0.31218(13) 0.0306(4) Uani 1.000000 .
N3 N 0.34348(14) -0.0132(3) 0.47401(13) 0.0308(4) Uani 1.000000 .
N1 N 0.15060(14) 0.5681(3) 0.23227(13) 0.0298(4) Uani 1.000000 .
C1 C 0.19258(16) 0.7466(3) 0.19739(14) 0.0282(4) Uani 1.000000 .
C8 C 0.24397(15) 0.2752(3) 0.35885(14) 0.0265(4) Uani 1.000000 .
C9 C 0.14016(15) 0.1781(3) 0.34677(14) 0.0294(4) Uani 1.000000 .
H9 H 0.06867(15) 0.2427(3) 0.30139(14) 0.0352(5) Uiso 1.000000 R
C6 C 0.31579(16) 0.7545(3) 0.24653(14) 0.0293(4) Uani 1.000000 .
C12 C 0.35311(15) 0.1768(3) 0.42666(14) 0.0284(4) Uani 1.000000 .
C7 C 0.24502(15) 0.4721(3) 0.30076(14) 0.0270(4) Uani 1.000000 .
C11 C 0.24027(17) -0.1086(3) 0.46235(15) 0.0315(4) Uani 1.000000 .
H11 H 0.24039(17) -0.2404(3) 0.49772(15) 0.0378(5) Uiso 1.000000 R
C10 C 0.13720(17) -0.0142(3) 0.39989(15) 0.0324(4) Uani 1.000000 .
H10 H 0.06480(17) -0.0771(3) 0.39235(15) 0.0389(5) Uiso 1.000000 R
C2 C 0.13183(19) 0.9095(3) 0.12664(15) 0.0346(5) Uani 1.000000 .
H2a H 0.04894(19) 0.9071(3) 0.09298(15) 0.0416(6) Uiso 1.000000 R
C3 C 0.1953(2) 1.0738(3) 0.10691(15) 0.0375(5) Uani 1.000000 .
H3a H 0.1552(2) 1.1868(3) 0.05984(15) 0.0451(6) Uiso 1.000000 R
C5 C 0.37980(19) 0.9185(3) 0.22540(16) 0.0375(5) Uani 1.000000 .
H5 H 0.46275(19) 0.9212(3) 0.25806(16) 0.0450(6) Uiso 1.000000 R
C4 C 0.3178(2) 1.0773(3) 0.15503(16) 0.0389(5) Uani 1.000000 .
H4 H 0.3591(2) 1.1912(3) 0.13887(16) 0.0467(6) Uiso 1.000000 R
H3 H 0.416(2) -0.084(4) 0.508(2) 0.051(7) Uiso 1.000000 .
H2 H 0.416(2) 0.537(4) 0.361(2) 0.048(7) Uiso 1.000000 .


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
O1 C12 1.259(2) . ?
N2 C6 1.380(2) . ?
N2 C7 1.375(2) . ?
N2 H2 0.90(3) . ?
N3 C12 1.374(2) . ?
N3 C11 1.366(3) . ?
N3 H3 0.95(3) . ?
N1 C1 1.388(2) . ?
N1 C7 1.322(2) . ?
C1 C6 1.412(3) . ?
C1 C2 1.398(3) . ?
C8 C9 1.376(3) . ?
C8 C12 1.444(2) . ?
C8 C7 1.461(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.406(3) . ?
C6 C5 1.392(3) . ?
C11 H11 0.9500 . ?
C11 C10 1.362(3) . ?
C10 H10 0.9500 . ?
C2 H2a 0.9500 . ?
C2 C3 1.380(3) . ?
C3 H3a 0.9500 . ?
C3 C4 1.404(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.382(3) . ?
C4 H4 0.9500 . ?

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
C7 N2 C6 107.23(15) . . ?
H2 N2 C6 130.5(17) . . ?
H2 N2 C7 121.8(17) . . ?
C11 N3 C12 124.77(16) . . ?
H3 N3 C12 112.6(16) . . ?
H3 N3 C11 122.1(16) . . ?
C7 N1 C1 104.74(15) . . ?
C6 C1 N1 110.41(15) . . ?
C2 C1 N1 129.92(18) . . ?
C2 C1 C6 119.65(18) . . ?
C12 C8 C9 119.55(17) . . ?
C7 C8 C9 120.72(16) . . ?
C7 C8 C12 119.68(15) . . ?
H9 C9 C8 119.16(11) . . ?
C10 C9 C8 121.67(17) . . ?
C10 C9 H9 119.16(10) . . ?
C1 C6 N2 104.74(16) . . ?
C5 C6 N2 133.31(18) . . ?
C5 C6 C1 121.95(17) . . ?
N3 C12 O1 119.30(15) . . ?
C8 C12 O1 125.16(17) . . ?
C8 C12 N3 115.54(15) . . ?
N1 C7 N2 112.87(17) . . ?
C8 C7 N2 122.57(15) . . ?
C8 C7 N1 124.56(16) . . ?
H11 C11 N3 120.09(11) . . ?
C10 C11 N3 119.82(18) . . ?
C10 C11 H11 120.09(12) . . ?
C11 C10 C9 118.62(18) . . ?
H10 C10 C9 120.69(10) . . ?
H10 C10 C11 120.69(12) . . ?
H2a C2 C1 120.82(12) . . ?
C3 C2 C1 118.4(2) . . ?
C3 C2 H2a 120.82(13) . . ?
H3a C3 C2 119.35(13) . . ?
C4 C3 C2 121.30(19) . . ?
C4 C3 H3a 119.35(12) . . ?
H5 C5 C6 121.34(12) . . ?
C4 C5 C6 117.3(2) . . ?
C4 C5 H5 121.34(13) . . ?
C5 C4 C3 121.39(19) . . ?
H4 C4 C3 119.30(12) . . ?
H4 C4 C5 119.30(13) . . ?

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
O1 C12 N3 C11 178.70(19) . . . . ?
O1 C12 C8 C9 -179.1(2) . . . . ?
O1 C12 C8 C7 3.2(2) . . . . ?
N2 C6 C1 N1 -0.29(17) . . . . ?
N2 C6 C1 C2 178.41(14) . . . . ?
N2 C6 C5 C4 -178.4(2) . . . . ?
N2 C7 N1 C1 -0.48(17) . . . . ?
N2 C7 C8 C9 178.62(19) . . . . ?
N2 C7 C8 C12 -3.7(2) . . . . ?
N3 C12 C8 C9 0.7(2) . . . . ?
N3 C12 C8 C7 -176.96(16) . . . . ?
N3 C11 C10 C9 1.4(2) . . . . ?
N1 C1 C6 C5 -179.84(16) . . . . ?
N1 C1 C2 C3 178.6(2) . . . . ?
N1 C7 C8 C9 -1.6(2) . . . . ?
N1 C7 C8 C12 175.99(19) . . . . ?
C1 C6 C5 C4 1.0(2) . . . . ?
C1 C2 C3 C4 0.9(2) . . . . ?
C8 C9 C10 C11 -1.9(2) . . . . ?
C6 C5 C4 C3 0.2(2) . . . . ?
C2 C3 C4 C5 -1.1(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_sss4_a
_database_code_depnum_ccdc_archive 'CCDC 2443162'
loop_
_audit_author_name
_audit_author_address
'Souvik Santra'
;University of Calcutta 
India
;
_audit_update_record             
;
2025-04-11 deposited with the CCDC.	2025-09-29 downloaded from the CCDC.
;
_audit_creation_date             2024-02-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H8 N2 O S'
_chemical_formula_sum            'C12 H8 N2 O S'
_chemical_formula_weight         228.26
_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                   11.450(4)
_cell_length_b                   4.9755(15)
_cell_length_c                   18.120(6)
_cell_angle_alpha                90
_cell_angle_beta                 104.206(11)
_cell_angle_gamma                90
_cell_volume                     1000.7(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4173
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      31.56
_cell_measurement_theta_min      2.32
_shelx_estimated_absorpt_T_max   0.723200
_shelx_estimated_absorpt_T_min   0.53800
_exptl_absorpt_coefficient_mu    0.298
_exptl_absorpt_correction_T_max  0.7232
_exptl_absorpt_correction_T_min  0.5380
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1477 before and 0.1174 after correction.
The Ratio of minimum to maximum transmission is 0.7439.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            transparent
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.74
_exptl_crystal_size_mid          0.58
_exptl_crystal_size_min          0.51
_exptl_transmission_factor_max   0.723200
_exptl_transmission_factor_min   0.53800
_diffrn_reflns_av_R_equivalents  0.1042
_diffrn_reflns_av_unetI/netI     0.1083
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.910
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            12942
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.712
_diffrn_reflns_theta_min         2.319
_diffrn_ambient_temperature      159.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.910
_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_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2249
_reflns_number_total             3640
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.654
_refine_diff_density_rms         0.122
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         3640
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1288
_refine_ls_R_factor_gt           0.0764
_refine_ls_restrained_S_all      1.070
_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)+(0.1385P)²+0.0746P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2001
_refine_ls_wR_factor_ref         0.2532
_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:
 C9(H9), C10(H10), C2(H2A), C11(H11), C5(H5), C4(H4), C3(H3)
;
_atom_sites_solution_hydrogens   mixed
_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
S1 S 0.39331(5) 0.55508(13) 0.40938(3) 0.0289(2) Uani 1 1 d . . . . .
O1 O 0.46247(15) 0.1888(4) 0.31395(11) 0.0326(4) Uani 1 1 d . . . . .
N2 N 0.3417(2) -0.0524(4) 0.21883(13) 0.0295(5) Uani 1 1 d . . . . .
N1 N 0.16481(19) 0.6238(4) 0.34780(12) 0.0299(5) Uani 1 1 d . . . . .
C12 C 0.3592(2) 0.1422(5) 0.27430(14) 0.0267(5) Uani 1 1 d . . . . .
C8 C 0.2514(2) 0.2784(5) 0.28274(14) 0.0263(5) Uani 1 1 d . . . . .
C6 C 0.1947(2) 0.7972(5) 0.40955(15) 0.0292(5) Uani 1 1 d . . . . .
C9 C 0.1413(2) 0.2081(5) 0.23575(15) 0.0298(5) Uani 1 1 d . . . . .
H9 H 0.070728 0.298291 0.241130 0.036 Uiso 1 1 calc R U . . .
C1 C 0.3155(2) 0.7842(5) 0.45142(15) 0.0285(5) Uani 1 1 d . . . . .
C10 C 0.1311(2) 0.0071(6) 0.18039(16) 0.0318(5) Uani 1 1 d . . . . .
H10 H 0.054789 -0.039446 0.148599 0.038 Uiso 1 1 calc R U . . .
C2 C 0.3574(3) 0.9442(5) 0.51621(15) 0.0335(6) Uani 1 1 d . . . . .
H2A H 0.438436 0.931935 0.545301 0.040 Uiso 1 1 calc R U . . .
C7 C 0.2590(2) 0.4842(5) 0.34141(14) 0.0268(5) Uani 1 1 d . . . . .
C11 C 0.2332(2) -0.1202(6) 0.17311(15) 0.0317(5) Uani 1 1 d . . . . .
H11 H 0.228266 -0.256925 0.135861 0.038 Uiso 1 1 calc R U . . .
C5 C 0.1151(3) 0.9762(6) 0.43172(17) 0.0368(6) Uani 1 1 d . . . . .
H5 H 0.033158 0.985763 0.404075 0.044 Uiso 1 1 calc R U . . .
C4 C 0.1576(3) 1.1380(6) 0.49429(17) 0.0395(7) Uani 1 1 d . . . . .
H4 H 0.104922 1.263378 0.508989 0.047 Uiso 1 1 calc R U . . .
C3 C 0.2774(3) 1.1201(6) 0.53646(16) 0.0372(6) Uani 1 1 d . . . . .
H3 H 0.304236 1.231320 0.579935 0.045 Uiso 1 1 calc R U . . .
H2 H 0.409(3) -0.142(8) 0.2131(18) 0.047(9) 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 C1 1.734(3) . ?
S1 C7 1.754(3) . ?
O1 C12 1.245(3) . ?
N2 C12 1.375(3) . ?
N2 C11 1.356(3) . ?
N2 H2 0.92(4) . ?
N1 C6 1.388(3) . ?
N1 C7 1.312(3) . ?
C12 C8 1.449(3) . ?
C8 C9 1.382(3) . ?
C8 C7 1.463(4) . ?
C6 C1 1.406(4) . ?
C6 C5 1.402(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.401(4) . ?
C1 C2 1.402(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.364(4) . ?
C2 H2A 0.9500 . ?
C2 C3 1.380(4) . ?
C11 H11 0.9500 . ?
C5 H5 0.9500 . ?
C5 C4 1.378(4) . ?
C4 H4 0.9500 . ?
C4 C3 1.400(4) . ?
C3 H3 0.9500 . ?

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
C1 S1 C7 89.11(12) . . ?
C12 N2 H2 117(2) . . ?
C11 N2 C12 124.7(2) . . ?
C11 N2 H2 119(2) . . ?
C7 N1 C6 110.8(2) . . ?
O1 C12 N2 120.0(2) . . ?
O1 C12 C8 124.4(2) . . ?
N2 C12 C8 115.6(2) . . ?
C12 C8 C7 120.2(2) . . ?
C9 C8 C12 119.2(2) . . ?
C9 C8 C7 120.5(2) . . ?
N1 C6 C1 114.9(2) . . ?
N1 C6 C5 125.2(2) . . ?
C5 C6 C1 119.8(2) . . ?
C8 C9 H9 119.2 . . ?
C8 C9 C10 121.7(2) . . ?
C10 C9 H9 119.2 . . ?
C6 C1 S1 109.67(19) . . ?
C2 C1 S1 129.4(2) . . ?
C2 C1 C6 121.0(2) . . ?
C9 C10 H10 120.7 . . ?
C11 C10 C9 118.6(2) . . ?
C11 C10 H10 120.7 . . ?
C1 C2 H2A 121.0 . . ?
C3 C2 C1 118.0(3) . . ?
C3 C2 H2A 121.0 . . ?
N1 C7 S1 115.46(19) . . ?
N1 C7 C8 122.1(2) . . ?
C8 C7 S1 122.47(18) . . ?
N2 C11 C10 120.3(2) . . ?
N2 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C6 C5 H5 120.5 . . ?
C4 C5 C6 118.9(3) . . ?
C4 C5 H5 120.5 . . ?
C5 C4 H4 119.6 . . ?
C5 C4 C3 120.8(3) . . ?
C3 C4 H4 119.6 . . ?
C2 C3 C4 121.4(3) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?

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 C1 C2 C3 177.5(2) . . . . ?
O1 C12 C8 C9 -179.5(2) . . . . ?
O1 C12 C8 C7 -0.7(4) . . . . ?
N2 C12 C8 C9 -0.4(3) . . . . ?
N2 C12 C8 C7 178.4(2) . . . . ?
N1 C6 C1 S1 2.0(3) . . . . ?
N1 C6 C1 C2 -178.6(2) . . . . ?
N1 C6 C5 C4 -179.7(3) . . . . ?
C12 N2 C11 C10 -0.2(4) . . . . ?
C12 C8 C9 C10 0.4(4) . . . . ?
C12 C8 C7 S1 -6.1(3) . . . . ?
C12 C8 C7 N1 175.7(2) . . . . ?
C8 C9 C10 C11 -0.2(4) . . . . ?
C6 N1 C7 S1 -0.9(3) . . . . ?
C6 N1 C7 C8 177.5(2) . . . . ?
C6 C1 C2 C3 -1.7(4) . . . . ?
C6 C5 C4 C3 -1.7(5) . . . . ?
C9 C8 C7 S1 172.71(19) . . . . ?
C9 C8 C7 N1 -5.6(4) . . . . ?
C9 C10 C11 N2 0.1(4) . . . . ?
C1 S1 C7 N1 1.7(2) . . . . ?
C1 S1 C7 C8 -176.7(2) . . . . ?
C1 C6 C5 C4 0.4(4) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
C7 S1 C1 C6 -1.99(19) . . . . ?
C7 S1 C1 C2 178.7(3) . . . . ?
C7 N1 C6 C1 -0.8(3) . . . . ?
C7 N1 C6 C5 179.3(3) . . . . ?
C7 C8 C9 C10 -178.4(2) . . . . ?
C11 N2 C12 O1 179.4(2) . . . . ?
C11 N2 C12 C8 0.3(4) . . . . ?
C5 C6 C1 S1 -178.1(2) . . . . ?
C5 C6 C1 C2 1.3(4) . . . . ?
C5 C4 C3 C2 1.2(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
