# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

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

data_MJK20180711
_database_code_depnum_ccdc_archive 'CCDC 1858182'
_audit_update_record             
;
2018-07-25 deposited with the CCDC.
2019-02-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H8 F4 N4 S'
_chemical_formula_weight         364.32

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'
F F 0.0171 0.0103 '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                   15.2261(8)
_cell_length_b                   4.4752(3)
_cell_length_c                   22.3479(12)
_cell_angle_alpha                90
_cell_angle_beta                 102.846(6)
_cell_angle_gamma                90
_cell_volume                     1484.67(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5869
_cell_measurement_theta_min      4.1070
_cell_measurement_theta_max      28.2510

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.271
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_T_min  0.49470
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.37b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12592
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.386
_diffrn_reflns_theta_max         26.364
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3040
_reflns_number_gt                2648
_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_data_collection       'CrysAlisPro 1.171.39.37b (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.37b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.37b (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0505P)²+0.5992P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3040
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1048
_refine_ls_wR_factor_gt          0.0998
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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
F1 F 0.71560(8) 1.1870(3) 0.79094(6) 0.0610(3) Uani 1 1 d . . . . .
F2 F 0.79989(7) 0.8701(3) 0.84726(7) 0.0641(4) Uani 1 1 d . . . . .
F3 F 0.75354(9) 1.2530(3) 0.88811(6) 0.0655(4) Uani 1 1 d . . . . .
N1 N 0.43728(10) 0.3243(4) 0.87656(6) 0.0401(4) Uani 1 1 d . . . . .
F4 F 0.35621(12) -0.2950(4) 0.48901(6) 0.0925(5) Uani 1 1 d . . . . .
N2 N 0.42710(11) 0.2278(4) 0.93258(7) 0.0516(4) Uani 1 1 d . . . . .
C11 C 0.52125(10) 0.5500(4) 0.80827(7) 0.0321(3) Uani 1 1 d . . . . .
C12 C 0.59260(11) 0.7372(4) 0.80222(7) 0.0342(4) Uani 1 1 d . . . . .
H12A H 0.6033 0.7713 0.7634 0.041 Uiso 1 1 calc R U . . .
C13 C 0.64757(11) 0.8726(4) 0.85273(8) 0.0356(4) Uani 1 1 d . . . . .
C7 C 0.50131(11) 0.3164(4) 0.70593(7) 0.0348(4) Uani 1 1 d . . . . .
H7A H 0.5603 0.3785 0.7083 0.042 Uiso 1 1 calc R U . . .
N4 N 0.31940(12) 0.0374(5) 0.86052(7) 0.0635(5) Uani 1 1 d . . . . .
N3 N 0.35692(12) 0.0601(5) 0.92202(8) 0.0628(5) Uani 1 1 d . . . . .
C4 C 0.45945(11) 0.1585(4) 0.64931(7) 0.0350(4) Uani 1 1 d . . . . .
C8 C 0.46767(11) 0.3853(4) 0.75483(7) 0.0337(4) Uani 1 1 d . . . . .
C10 C 0.50719(11) 0.5174(4) 0.86800(7) 0.0354(4) Uani 1 1 d . . . . .
C16 C 0.72817(12) 1.0461(4) 0.84485(8) 0.0401(4) Uani 1 1 d . . . . .
C5 C 0.51466(12) -0.0187(4) 0.62147(8) 0.0414(4) Uani 1 1 d . . . . .
H5A H 0.5758 -0.0320 0.6393 0.050 Uiso 1 1 calc R U . . .
C14 C 0.63118(12) 0.8347(4) 0.91092(8) 0.0426(4) Uani 1 1 d . . . . .
H14A H 0.6678 0.9277 0.9446 0.051 Uiso 1 1 calc R U . . .
C9 C 0.37062(12) 0.2045(5) 0.83367(8) 0.0455(5) Uani 1 1 d . . . . .
C15 C 0.56031(12) 0.6582(5) 0.91832(8) 0.0439(4) Uani 1 1 d . . . . .
H15A H 0.5482 0.6338 0.9570 0.053 Uiso 1 1 calc R U . . .
C3 C 0.36866(13) 0.1837(5) 0.62040(8) 0.0481(5) Uani 1 1 d . . . . .
H3B H 0.3311 0.3046 0.6375 0.058 Uiso 1 1 calc R U . . .
C6 C 0.48037(15) -0.1740(5) 0.56815(9) 0.0519(5) Uani 1 1 d . . . . .
H6A H 0.5173 -0.2948 0.5504 0.062 Uiso 1 1 calc R U . . .
C1 C 0.39046(16) -0.1456(5) 0.54206(9) 0.0565(6) Uani 1 1 d . . . . .
C2 C 0.33382(14) 0.0309(6) 0.56649(9) 0.0597(6) Uani 1 1 d . . . . .
H2B H 0.2732 0.0478 0.5473 0.072 Uiso 1 1 calc R U . . .
S1 S 0.35513(3) 0.27677(15) 0.75606(2) 0.05490(19) 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
F1 C16 1.335(2) . ?
F2 C16 1.338(2) . ?
F3 C16 1.333(2) . ?
N1 C9 1.343(2) . ?
N1 N2 1.365(2) . ?
N1 C10 1.417(2) . ?
F4 C1 1.360(2) . ?
N2 N3 1.284(2) . ?
C11 C12 1.402(2) . ?
C11 C10 1.406(2) . ?
C11 C8 1.484(2) . ?
C12 C13 1.386(2) . ?
C12 H12A 0.9300 . ?
C13 C14 1.388(2) . ?
C13 C16 1.496(2) . ?
C7 C8 1.342(2) . ?
C7 C4 1.466(2) . ?
C7 H7A 0.9300 . ?
N4 C9 1.317(2) . ?
N4 N3 1.370(2) . ?
C4 C5 1.398(2) . ?
C4 C3 1.394(2) . ?
C8 S1 1.7870(16) . ?
C10 C15 1.383(2) . ?
C5 C6 1.378(3) . ?
C5 H5A 0.9300 . ?
C14 C15 1.376(3) . ?
C14 H14A 0.9300 . ?
C9 S1 1.7281(19) . ?
C15 H15A 0.9300 . ?
C3 C2 1.384(3) . ?
C3 H3B 0.9300 . ?
C6 C1 1.369(3) . ?
C6 H6A 0.9300 . ?
C1 C2 1.369(3) . ?
C2 H2B 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
C9 N1 N2 107.84(15) . . ?
C9 N1 C10 128.20(15) . . ?
N2 N1 C10 123.95(15) . . ?
N3 N2 N1 106.00(15) . . ?
C12 C11 C10 116.01(15) . . ?
C12 C11 C8 121.22(14) . . ?
C10 C11 C8 122.69(15) . . ?
C13 C12 C11 121.54(15) . . ?
C13 C12 H12A 119.2 . . ?
C11 C12 H12A 119.2 . . ?
C14 C13 C12 120.52(16) . . ?
C14 C13 C16 119.80(16) . . ?
C12 C13 C16 119.59(15) . . ?
C8 C7 C4 129.97(16) . . ?
C8 C7 H7A 115.0 . . ?
C4 C7 H7A 115.0 . . ?
C9 N4 N3 104.94(17) . . ?
N2 N3 N4 111.85(16) . . ?
C5 C4 C3 118.15(16) . . ?
C5 C4 C7 117.94(15) . . ?
C3 C4 C7 123.86(16) . . ?
C7 C8 C11 121.90(15) . . ?
C7 C8 S1 119.40(13) . . ?
C11 C8 S1 118.69(11) . . ?
C15 C10 C11 122.68(16) . . ?
C15 C10 N1 119.31(15) . . ?
C11 C10 N1 117.98(15) . . ?
F3 C16 F1 106.66(15) . . ?
F3 C16 F2 106.12(15) . . ?
F1 C16 F2 105.45(14) . . ?
F3 C16 C13 112.86(15) . . ?
F1 C16 C13 113.25(14) . . ?
F2 C16 C13 111.93(14) . . ?
C6 C5 C4 121.42(18) . . ?
C6 C5 H5A 119.3 . . ?
C4 C5 H5A 119.3 . . ?
C15 C14 C13 119.45(16) . . ?
C15 C14 H14A 120.3 . . ?
C13 C14 H14A 120.3 . . ?
N4 C9 N1 109.36(16) . . ?
N4 C9 S1 126.93(15) . . ?
N1 C9 S1 123.67(14) . . ?
C14 C15 C10 119.75(16) . . ?
C14 C15 H15A 120.1 . . ?
C10 C15 H15A 120.1 . . ?
C2 C3 C4 120.80(19) . . ?
C2 C3 H3B 119.6 . . ?
C4 C3 H3B 119.6 . . ?
C1 C6 C5 118.16(19) . . ?
C1 C6 H6A 120.9 . . ?
C5 C6 H6A 120.9 . . ?
F4 C1 C2 118.5(2) . . ?
F4 C1 C6 118.6(2) . . ?
C2 C1 C6 122.85(19) . . ?
C1 C2 C3 118.59(19) . . ?
C1 C2 H2B 120.7 . . ?
C3 C2 H2B 120.7 . . ?
C9 S1 C8 98.56(8) . . ?

_refine_diff_density_max         0.190
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.051



####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1882658'
_audit_update_record             
;
2018-12-03 deposited with the CCDC.
2019-02-01 downloaded from the CCDC.
;
_audit_creation_date             2018-10-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014-1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C12 H10 N4 S'
_chemical_formula_sum            'C12 H0.12 N4 S'
_chemical_formula_weight         232.35
_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'
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'
H H 0.0000 0.0000 '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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   14.8813(8)
_cell_length_b                   8.3305(5)
_cell_length_c                   18.5422(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2298.7(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.260
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             929
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            17077
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.246
_diffrn_reflns_theta_min         3.511
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1953
_reflns_number_total             2896
_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       ?
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.677
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2896
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0615
_refine_ls_restrained_S_all      1.053
_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)+(0.0740P)²+1.2719P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1565
_refine_ls_wR_factor_ref         0.1756
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C1(H1), C4(H4), C2(H2), C3(H3)
;
_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 0.73088(5) 0.57073(9) 0.60404(4) 0.0554(3) Uani 1 1 d . . . . .
N1 N 0.84768(12) 0.6751(2) 0.70615(13) 0.0516(5) Uani 1 1 d . . . . .
N4 N 0.88861(16) 0.7376(3) 0.59760(16) 0.0732(8) Uani 1 1 d . . . . .
N2 N 0.92693(15) 0.7540(3) 0.71155(19) 0.0754(8) Uani 1 1 d . . . . .
N3 N 0.95023(17) 0.7884(4) 0.6462(2) 0.0892(10) Uani 1 1 d . . . . .
C7 C 0.82553(16) 0.6684(3) 0.63606(16) 0.0511(6) Uani 1 1 d . . . . .
C5 C 0.80520(18) 0.6064(3) 0.76721(14) 0.0515(6) Uani 1 1 d . . . . .
C9 C 0.64796(15) 0.6815(3) 0.65416(15) 0.0494(6) Uani 1 1 d . . . . .
C6 C 0.71161(18) 0.6097(3) 0.77494(14) 0.0503(6) Uani 1 1 d . . . . .
C8 C 0.64915(15) 0.6849(3) 0.72479(15) 0.0504(6) Uani 1 1 d . . . . .
H8 H 0.6033 0.7440 0.7461 0.060 Uiso 1 1 calc R . . . .
C10 C 0.5756(2) 0.7605(4) 0.61192(17) 0.0674(8) Uani 1 1 d . . . . .
H10 H 0.5322 0.8203 0.6413 0.081 Uiso 1 1 calc R . . . .
C1 C 0.6771(3) 0.5419(4) 0.83819(16) 0.0723(9) Uani 1 1 d . . . . .
H1 H 0.6154 0.5440 0.8460 0.087 Uiso 1 1 calc R . . . .
C4 C 0.8598(2) 0.5383(4) 0.81986(18) 0.0737(9) Uani 1 1 d . . . . .
H4 H 0.9219 0.5388 0.8141 0.088 Uiso 1 1 calc R . . . .
C12 C 0.5912(2) 0.8294(4) 0.53983(19) 0.0808(10) Uani 1 1 d . . . . .
H12A H 0.5607 0.9288 0.5279 0.097 Uiso 1 1 calc R . . . .
H12B H 0.6507 0.8181 0.5191 0.097 Uiso 1 1 calc R . . . .
C11 C 0.5364(2) 0.6840(4) 0.54753(18) 0.0784(10) Uani 1 1 d . . . . .
H11A H 0.5621 0.5831 0.5316 0.094 Uiso 1 1 calc R . . . .
H11B H 0.4720 0.6938 0.5403 0.094 Uiso 1 1 calc R . . . .
C2 C 0.7319(3) 0.4724(5) 0.88899(18) 0.0889(13) Uani 1 1 d . . . . .
H2 H 0.7067 0.4262 0.9299 0.107 Uiso 1 1 calc R . . . .
C3 C 0.8228(4) 0.4705(5) 0.8799(2) 0.0931(12) Uani 1 1 d . . . . .
H3 H 0.8594 0.4233 0.9146 0.112 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C7 1.732(3) . ?
S1 C9 1.800(3) . ?
N1 N2 1.354(3) . ?
N1 C7 1.342(3) . ?
N1 C5 1.417(4) . ?
N4 N3 1.354(4) . ?
N4 C7 1.312(3) . ?
N2 N3 1.292(4) . ?
C5 C6 1.400(4) . ?
C5 C4 1.391(4) . ?
C9 C8 1.310(4) . ?
C9 C10 1.486(4) . ?
C6 C8 1.456(3) . ?
C6 C1 1.399(4) . ?
C10 C12 1.474(4) . ?
C10 C11 1.474(4) . ?
C1 C2 1.374(5) . ?
C4 C3 1.365(5) . ?
C12 C11 1.468(4) . ?
C2 C3 1.363(6) . ?

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 S1 C9 98.03(12) . . ?
N2 N1 C5 121.7(2) . . ?
C7 N1 N2 107.8(2) . . ?
C7 N1 C5 130.3(2) . . ?
C7 N4 N3 105.1(3) . . ?
N3 N2 N1 105.8(3) . . ?
N2 N3 N4 111.9(2) . . ?
N1 C7 S1 123.46(19) . . ?
N4 C7 S1 127.0(2) . . ?
N4 C7 N1 109.4(2) . . ?
C6 C5 N1 121.2(2) . . ?
C4 C5 N1 117.7(3) . . ?
C4 C5 C6 121.1(3) . . ?
C8 C9 S1 121.19(19) . . ?
C8 C9 C10 121.8(2) . . ?
C10 C9 S1 116.9(2) . . ?
C5 C6 C8 125.3(2) . . ?
C1 C6 C5 116.3(3) . . ?
C1 C6 C8 118.3(3) . . ?
C9 C8 C6 129.6(2) . . ?
C12 C10 C9 122.4(3) . . ?
C12 C10 C11 59.8(2) . . ?
C11 C10 C9 121.5(3) . . ?
C2 C1 C6 121.8(3) . . ?
C3 C4 C5 120.4(3) . . ?
C11 C12 C10 60.1(2) . . ?
C12 C11 C10 60.1(2) . . ?
C3 C2 C1 120.6(3) . . ?
C2 C3 C4 119.7(3) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
