# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 2022218'
loop_
_audit_author_name
_audit_author_address
'O. Blacque'
;University of Zurich
Switzerland
;
_audit_update_record             
;
2020-08-08 deposited with the CCDC.	2020-09-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H9 N3 O S2'
_chemical_formula_weight         263.33

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.5546(2)
_cell_length_b                   4.9907(5)
_cell_length_c                   17.1813(3)
_cell_angle_alpha                90
_cell_angle_beta                 113.268(2)
_cell_angle_gamma                90
_cell_volume                     1146.50(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    160(1)
_cell_measurement_reflns_used    7920
_cell_measurement_theta_max      79.0
_cell_measurement_theta_min      3.4

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    4.102
_shelx_estimated_absorpt_T_min   0.709
_shelx_estimated_absorpt_T_max   0.887
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.745
_exptl_absorpt_correction_T_max  0.908
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.39a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      160(1)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            11447
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.384
_diffrn_reflns_theta_max         74.466
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2336
_reflns_number_gt                2147
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_cell_refinement       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015b)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015a)'
_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)+(0.0358P)²+0.4259P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2336
_refine_ls_number_parameters     159
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0270
_refine_ls_R_factor_gt           0.0249
_refine_ls_wR_factor_ref         0.0687
_refine_ls_wR_factor_gt          0.0674
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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 0.42521(2) 0.59528(7) 0.34017(2) 0.02616(11) Uani 1 1 d . . . . .
S2 S 0.76320(2) 0.74865(6) 0.32497(2) 0.02129(10) Uani 1 1 d . . . . .
O6 O 0.62778(7) -0.0907(2) 0.53533(6) 0.0268(2) Uani 1 1 d . . . . .
N3 N 0.61745(8) 0.5081(2) 0.37174(7) 0.0201(2) Uani 1 1 d . . . . .
N2 N 0.87904(10) -0.0633(3) 0.56368(8) 0.0339(3) Uani 1 1 d . . . . .
N1 N 0.54303(9) 0.2397(2) 0.44340(8) 0.0226(2) Uani 1 1 d . . . . .
H1 H 0.4878(16) 0.195(4) 0.4500(13) 0.043(5) Uiso 1 1 d . . . . .
C2 C 0.54074(10) 0.4376(3) 0.38833(8) 0.0206(3) Uani 1 1 d . . . . .
C6 C 0.62894(10) 0.0950(3) 0.48798(8) 0.0215(3) Uani 1 1 d . . . . .
C5 C 0.71540(9) 0.1793(3) 0.47324(8) 0.0203(3) Uani 1 1 d . . . . .
C4 C 0.70668(9) 0.3793(3) 0.41452(8) 0.0184(3) Uani 1 1 d . . . . .
C7 C 0.44546(10) 0.8079(3) 0.26273(9) 0.0258(3) Uani 1 1 d . . . . .
H71 H 0.498770 0.940227 0.291544 0.031 Uiso 1 1 calc R U . . .
H72 H 0.466061 0.698405 0.224329 0.031 Uiso 1 1 calc R U . . .
C8 C 0.34727(12) 0.9505(3) 0.21272(10) 0.0352(4) Uani 1 1 d . . . . .
H81 H 0.324724 1.045665 0.251883 0.053 Uiso 1 1 calc R U . . .
H82 H 0.296669 0.818608 0.180453 0.053 Uiso 1 1 calc R U . . .
H83 H 0.357198 1.079059 0.173626 0.053 Uiso 1 1 calc R U . . .
C9 C 0.80637(10) 0.0445(3) 0.52234(9) 0.0233(3) Uani 1 1 d . . . . .
C10 C 0.78716(9) 0.4741(3) 0.39190(8) 0.0187(3) Uani 1 1 d . . . . .
C11 C 0.88466(10) 0.3844(3) 0.41504(8) 0.0210(3) Uani 1 1 d . . . . .
H11 H 0.912243 0.235258 0.451109 0.025 Uiso 1 1 calc R U . . .
C12 C 0.93798(10) 0.5417(3) 0.37841(9) 0.0236(3) Uani 1 1 d . . . . .
H12 H 1.005713 0.509391 0.387277 0.028 Uiso 1 1 calc R U . . .
C13 C 0.88233(10) 0.7440(3) 0.32922(9) 0.0241(3) Uani 1 1 d . . . . .
H13 H 0.907012 0.868893 0.300427 0.029 Uiso 1 1 calc R U . . .


_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 C2 1.7412(13) . ?
S1 C7 1.8143(14) . ?
S2 C13 1.7065(14) . ?
S2 C10 1.7331(13) . ?
O6 C6 1.2376(17) . ?
N3 C2 1.3049(17) . ?
N3 C4 1.3733(17) . ?
N2 C9 1.1484(19) . ?
N1 C2 1.3590(18) . ?
N1 C6 1.3839(18) . ?
N1 H1 0.88(2) . ?
C6 C5 1.4411(18) . ?
C5 C4 1.3887(19) . ?
C5 C9 1.4266(19) . ?
C4 C10 1.4515(17) . ?
C7 C8 1.522(2) . ?
C7 H71 0.9900 . ?
C7 H72 0.9900 . ?
C8 H81 0.9800 . ?
C8 H82 0.9800 . ?
C8 H83 0.9800 . ?
C10 C11 1.3882(18) . ?
C11 C12 1.4144(19) . ?
C11 H11 0.9500 . ?
C12 C13 1.360(2) . ?
C12 H12 0.9500 . ?
C13 H13 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
C2 S1 C7 101.93(6) . . ?
C13 S2 C10 91.50(6) . . ?
C2 N3 C4 117.83(11) . . ?
C2 N1 C6 122.20(12) . . ?
C2 N1 H1 120.0(14) . . ?
C6 N1 H1 117.7(14) . . ?
N3 C2 N1 124.07(12) . . ?
N3 C2 S1 121.56(10) . . ?
N1 C2 S1 114.37(10) . . ?
O6 C6 N1 120.71(12) . . ?
O6 C6 C5 125.02(12) . . ?
N1 C6 C5 114.27(11) . . ?
C4 C5 C9 124.46(12) . . ?
C4 C5 C6 120.13(12) . . ?
C9 C5 C6 115.41(12) . . ?
N3 C4 C5 121.39(12) . . ?
N3 C4 C10 113.36(11) . . ?
C5 C4 C10 125.25(12) . . ?
C8 C7 S1 107.41(10) . . ?
C8 C7 H71 110.2 . . ?
S1 C7 H71 110.2 . . ?
C8 C7 H72 110.2 . . ?
S1 C7 H72 110.2 . . ?
H71 C7 H72 108.5 . . ?
C7 C8 H81 109.5 . . ?
C7 C8 H82 109.5 . . ?
H81 C8 H82 109.5 . . ?
C7 C8 H83 109.5 . . ?
H81 C8 H83 109.5 . . ?
H82 C8 H83 109.5 . . ?
N2 C9 C5 178.24(15) . . ?
C11 C10 C4 131.28(12) . . ?
C11 C10 S2 111.11(10) . . ?
C4 C10 S2 117.61(9) . . ?
C10 C11 C12 111.83(12) . . ?
C10 C11 H11 124.1 . . ?
C12 C11 H11 124.1 . . ?
C13 C12 C11 113.08(12) . . ?
C13 C12 H12 123.5 . . ?
C11 C12 H12 123.5 . . ?
C12 C13 S2 112.48(10) . . ?
C12 C13 H13 123.8 . . ?
S2 C13 H13 123.8 . . ?

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
C4 N3 C2 N1 -1.99(19) . . . . ?
C4 N3 C2 S1 177.95(9) . . . . ?
C6 N1 C2 N3 0.6(2) . . . . ?
C6 N1 C2 S1 -179.34(10) . . . . ?
C7 S1 C2 N3 7.47(13) . . . . ?
C7 S1 C2 N1 -172.58(10) . . . . ?
C2 N1 C6 O6 -177.32(13) . . . . ?
C2 N1 C6 C5 2.23(19) . . . . ?
O6 C6 C5 C4 175.84(13) . . . . ?
N1 C6 C5 C4 -3.68(18) . . . . ?
O6 C6 C5 C9 -4.2(2) . . . . ?
N1 C6 C5 C9 176.31(12) . . . . ?
C2 N3 C4 C5 0.36(18) . . . . ?
C2 N3 C4 C10 -179.52(11) . . . . ?
C9 C5 C4 N3 -177.45(12) . . . . ?
C6 C5 C4 N3 2.55(19) . . . . ?
C9 C5 C4 C10 2.4(2) . . . . ?
C6 C5 C4 C10 -177.59(12) . . . . ?
C2 S1 C7 C8 177.57(11) . . . . ?
N3 C4 C10 C11 -174.27(13) . . . . ?
C5 C4 C10 C11 5.9(2) . . . . ?
N3 C4 C10 S2 6.23(15) . . . . ?
C5 C4 C10 S2 -173.64(10) . . . . ?
C13 S2 C10 C11 -0.62(10) . . . . ?
C13 S2 C10 C4 178.97(10) . . . . ?
C4 C10 C11 C12 -179.08(13) . . . . ?
S2 C10 C11 C12 0.45(14) . . . . ?
C10 C11 C12 C13 0.04(17) . . . . ?
C11 C12 C13 S2 -0.52(16) . . . . ?
C10 S2 C13 C12 0.65(11) . . . . ?

_refine_diff_density_max         0.287
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2022219'
loop_
_audit_author_name
_audit_author_address
'O. Blacque'
;University of Zurich
Switzerland
;
_audit_update_record             
;
2020-08-08 deposited with the CCDC.	2020-09-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H11 N3 O S'
_chemical_formula_weight         257.31

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   4.6908(2)
_cell_length_b                   9.2376(3)
_cell_length_c                   14.6613(3)
_cell_angle_alpha                94.308(2)
_cell_angle_beta                 93.766(2)
_cell_angle_gamma                100.924(3)
_cell_volume                     619.95(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    160(1)
_cell_measurement_reflns_used    7574
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      77.7

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_F_000             268
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    2.248
_shelx_estimated_absorpt_T_min   0.759
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.848
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.39a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      160(1)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            13068
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.033
_diffrn_reflns_theta_max         74.464
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2524
_reflns_number_gt                2219
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_cell_refinement       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015b)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015a)'
_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)+(0.0485P)²+0.1743P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2524
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0327
_refine_ls_wR_factor_ref         0.0888
_refine_ls_wR_factor_gt          0.0859
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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_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 -0.07309(8) 0.14886(4) 0.90110(2) 0.03368(13) Uani 1 1 d . . . . .
O6 O 0.7377(2) 0.56822(12) 0.92095(7) 0.0377(3) Uani 1 1 d . . . . .
N3 N 0.2302(3) 0.22848(13) 0.75839(8) 0.0275(3) Uani 1 1 d . . . . .
N2 N 1.0506(4) 0.6220(2) 0.72002(10) 0.0665(6) Uani 1 1 d . . . . .
N1 N 0.3520(3) 0.37484(13) 0.89931(8) 0.0299(3) Uani 1 1 d . . . . .
H1 H 0.316(4) 0.392(2) 0.9587(16) 0.057(6) Uiso 1 1 d . . . . .
C2 C 0.1928(3) 0.25870(15) 0.84511(10) 0.0278(3) Uani 1 1 d . . . . .
C6 C 0.5843(3) 0.46832(15) 0.86887(9) 0.0292(3) Uani 1 1 d . . . . .
C5 C 0.6264(3) 0.43784(15) 0.77324(9) 0.0277(3) Uani 1 1 d . . . . .
C4 C 0.4474(3) 0.32038(15) 0.72078(9) 0.0254(3) Uani 1 1 d . . . . .
C7 C -0.2329(3) 0.00253(17) 0.81269(11) 0.0360(3) Uani 1 1 d . . . . .
H71 H -0.330130 0.043534 0.761410 0.043 Uiso 1 1 calc R U . . .
H72 H -0.080550 -0.046990 0.788338 0.043 Uiso 1 1 calc R U . . .
C8 C -0.4520(4) -0.1060(2) 0.85724(13) 0.0495(4) Uani 1 1 d . . . . .
H81 H -0.552643 -0.184146 0.810913 0.074 Uiso 1 1 calc R U . . .
H82 H -0.594290 -0.054168 0.884340 0.074 Uiso 1 1 calc R U . . .
H83 H -0.351000 -0.150108 0.905368 0.074 Uiso 1 1 calc R U . . .
C9 C 0.8597(4) 0.53841(18) 0.74085(10) 0.0377(4) Uani 1 1 d . . . . .
C10 C 0.4687(3) 0.28429(15) 0.62158(9) 0.0257(3) Uani 1 1 d . . . . .
C11A C 0.7349(6) 0.3195(3) 0.58165(19) 0.0288(7) Uani 0.501(3) 1 d . . P A 1
H111 H 0.907480 0.362822 0.619089 0.035 Uiso 0.501(3) 1 calc R U P A 1
C11B C 0.5757(6) 0.3944(3) 0.56483(19) 0.0300(7) Uani 0.499(3) 1 d . . P A 2
H112 H 0.638403 0.494030 0.590053 0.036 Uiso 0.499(3) 1 calc R U P A 2
C12A C 0.7465(6) 0.2912(3) 0.48760(19) 0.0299(7) Uani 0.501(3) 1 d . . P A 1
H121 H 0.924366 0.319802 0.460270 0.036 Uiso 0.501(3) 1 calc R U P A 1
C12B C 0.5900(7) 0.3581(3) 0.4721(2) 0.0330(7) Uani 0.499(3) 1 d . . P A 2
H122 H 0.669271 0.433239 0.434938 0.040 Uiso 0.499(3) 1 calc R U P A 2
C13 C 0.4954(3) 0.22053(17) 0.43356(10) 0.0318(3) Uani 1 1 d . . . . .
H131 H 0.505377 0.195620 0.369949 0.038 Uiso 0.501(3) 1 calc R U P A 1
H132 H 0.501799 0.198819 0.369442 0.038 Uiso 0.499(3) 1 calc R U P A 2
C14A C 0.2349(7) 0.1869(3) 0.4717(2) 0.0328(7) Uani 0.501(3) 1 d . . P A 1
H141 H 0.062719 0.144981 0.433782 0.039 Uiso 0.501(3) 1 calc R U P A 1
C14B C 0.3835(6) 0.1050(3) 0.49002(19) 0.0300(7) Uani 0.499(3) 1 d . . P A 2
H142 H 0.321559 0.005754 0.463919 0.036 Uiso 0.499(3) 1 calc R U P A 2
C15A C 0.2212(6) 0.2139(3) 0.56574(19) 0.0301(7) Uani 0.501(3) 1 d . . P A 1
H151 H 0.042145 0.184157 0.592197 0.036 Uiso 0.501(3) 1 calc R U P A 1
C15B C 0.3672(6) 0.1403(3) 0.58279(19) 0.0277(7) Uani 0.499(3) 1 d . . P A 2
H152 H 0.286210 0.065741 0.620075 0.033 Uiso 0.499(3) 1 calc R U P A 2


_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 C2 1.7432(14) . ?
S1 C7 1.8150(15) . ?
O6 C6 1.2339(17) . ?
N3 C2 1.3113(18) . ?
N3 C4 1.3707(18) . ?
N2 C9 1.141(2) . ?
N1 C2 1.3531(18) . ?
N1 C6 1.3775(18) . ?
N1 H1 0.91(2) . ?
C6 C5 1.4429(19) . ?
C5 C4 1.385(2) . ?
C5 C9 1.427(2) . ?
C4 C10 1.4817(19) . ?
C7 C8 1.511(2) . ?
C7 H71 0.9900 . ?
C7 H72 0.9900 . ?
C8 H81 0.9800 . ?
C8 H82 0.9800 . ?
C8 H83 0.9800 . ?
C10 C15B 1.389(3) . ?
C10 C15A 1.397(3) . ?
C10 C11B 1.402(3) . ?
C10 C11A 1.407(3) . ?
C11A C12A 1.391(4) . ?
C11A H111 0.9500 . ?
C11B C12B 1.385(4) . ?
C11B H112 0.9500 . ?
C12A C13 1.396(3) . ?
C12A H121 0.9500 . ?
C12B C13 1.333(3) . ?
C12B H122 0.9500 . ?
C13 C14A 1.369(3) . ?
C13 C14B 1.442(3) . ?
C13 H131 0.9500 . ?
C13 H132 0.9500 . ?
C14A C15A 1.390(4) . ?
C14A H141 0.9500 . ?
C14B C15B 1.385(4) . ?
C14B H142 0.9500 . ?
C15A H151 0.9500 . ?
C15B H152 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
C2 S1 C7 102.73(7) . . ?
C2 N3 C4 117.49(12) . . ?
C2 N1 C6 122.14(12) . . ?
C2 N1 H1 121.4(14) . . ?
C6 N1 H1 116.4(14) . . ?
N3 C2 N1 124.39(13) . . ?
N3 C2 S1 121.82(11) . . ?
N1 C2 S1 113.79(10) . . ?
O6 C6 N1 121.16(12) . . ?
O6 C6 C5 124.75(13) . . ?
N1 C6 C5 114.09(12) . . ?
C4 C5 C9 125.41(13) . . ?
C4 C5 C6 120.55(12) . . ?
C9 C5 C6 114.04(12) . . ?
N3 C4 C5 121.17(12) . . ?
N3 C4 C10 114.71(12) . . ?
C5 C4 C10 124.11(12) . . ?
C8 C7 S1 106.66(11) . . ?
C8 C7 H71 110.4 . . ?
S1 C7 H71 110.4 . . ?
C8 C7 H72 110.4 . . ?
S1 C7 H72 110.4 . . ?
H71 C7 H72 108.6 . . ?
C7 C8 H81 109.5 . . ?
C7 C8 H82 109.5 . . ?
H81 C8 H82 109.5 . . ?
C7 C8 H83 109.5 . . ?
H81 C8 H83 109.5 . . ?
H82 C8 H83 109.5 . . ?
N2 C9 C5 176.09(16) . . ?
C15B C10 C11B 119.08(19) . . ?
C15A C10 C11A 118.68(19) . . ?
C15B C10 C4 119.60(15) . . ?
C15A C10 C4 119.96(16) . . ?
C11B C10 C4 121.23(16) . . ?
C11A C10 C4 121.36(16) . . ?
C12A C11A C10 120.3(2) . . ?
C12A C11A H111 119.9 . . ?
C10 C11A H111 119.9 . . ?
C12B C11B C10 120.1(2) . . ?
C12B C11B H112 119.9 . . ?
C10 C11B H112 119.9 . . ?
C11A C12A C13 119.6(2) . . ?
C11A C12A H121 120.2 . . ?
C13 C12A H121 120.2 . . ?
C13 C12B C11B 121.8(3) . . ?
C13 C12B H122 119.1 . . ?
C11B C12B H122 119.1 . . ?
C14A C13 C12A 120.4(2) . . ?
C12B C13 C14B 119.43(19) . . ?
C14A C13 H131 119.8 . . ?
C12A C13 H131 119.8 . . ?
C12B C13 H132 120.3 . . ?
C14B C13 H132 120.3 . . ?
C13 C14A C15A 120.3(3) . . ?
C13 C14A H141 119.8 . . ?
C15A C14A H141 119.8 . . ?
C15B C14B C13 119.2(2) . . ?
C15B C14B H142 120.4 . . ?
C13 C14B H142 120.4 . . ?
C14A C15A C10 120.5(2) . . ?
C14A C15A H151 119.8 . . ?
C10 C15A H151 119.8 . . ?
C14B C15B C10 120.3(2) . . ?
C14B C15B H152 119.8 . . ?
C10 C15B H152 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
C4 N3 C2 N1 0.6(2) . . . . ?
C4 N3 C2 S1 -179.20(10) . . . . ?
C6 N1 C2 N3 -4.1(2) . . . . ?
C6 N1 C2 S1 175.68(11) . . . . ?
C7 S1 C2 N3 2.07(14) . . . . ?
C7 S1 C2 N1 -177.77(11) . . . . ?
C2 N1 C6 O6 -175.59(14) . . . . ?
C2 N1 C6 C5 4.5(2) . . . . ?
O6 C6 C5 C4 178.21(14) . . . . ?
N1 C6 C5 C4 -1.9(2) . . . . ?
O6 C6 C5 C9 -2.3(2) . . . . ?
N1 C6 C5 C9 177.60(13) . . . . ?
C2 N3 C4 C5 2.1(2) . . . . ?
C2 N3 C4 C10 -177.19(12) . . . . ?
C9 C5 C4 N3 179.26(14) . . . . ?
C6 C5 C4 N3 -1.3(2) . . . . ?
C9 C5 C4 C10 -1.6(2) . . . . ?
C6 C5 C4 C10 177.83(13) . . . . ?
C2 S1 C7 C8 175.62(12) . . . . ?
N3 C4 C10 C15B -25.4(2) . . . . ?
C5 C4 C10 C15B 155.37(18) . . . . ?
N3 C4 C10 C15A 27.8(2) . . . . ?
C5 C4 C10 C15A -151.43(19) . . . . ?
N3 C4 C10 C11B 151.21(18) . . . . ?
C5 C4 C10 C11B -28.0(2) . . . . ?
N3 C4 C10 C11A -152.21(18) . . . . ?
C5 C4 C10 C11A 28.6(2) . . . . ?
C15A C10 C11A C12A 3.2(3) . . . . ?
C4 C10 C11A C12A -176.8(2) . . . . ?
C15B C10 C11B C12B -2.5(4) . . . . ?
C4 C10 C11B C12B -179.2(2) . . . . ?
C10 C11A C12A C13 -3.3(4) . . . . ?
C10 C11B C12B C13 2.2(4) . . . . ?
C11B C12B C13 C14B -2.0(4) . . . . ?
C11A C12A C13 C14A 3.8(4) . . . . ?
C12A C13 C14A C15A -4.3(4) . . . . ?
C12B C13 C14B C15B 2.2(4) . . . . ?
C13 C14A C15A C10 4.2(4) . . . . ?
C11A C10 C15A C14A -3.6(4) . . . . ?
C4 C10 C15A C14A 176.4(2) . . . . ?
C13 C14B C15B C10 -2.6(4) . . . . ?
C11B C10 C15B C14B 2.8(4) . . . . ?
C4 C10 C15B C14B 179.5(2) . . . . ?

_refine_diff_density_max         0.303
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.041

