# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_SRA1
_database_code_depnum_ccdc_archive 'CCDC 1879083'
_audit_update_record             
;
2018-11-14 deposited with the CCDC.
2018-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H3 N S3'
_chemical_formula_weight         209.29

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'Pca2(1) '

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

_cell_length_a                   30.935(4)
_cell_length_b                   3.8492(5)
_cell_length_c                   13.9128(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1656.7(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4214
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      26.60

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    0.826
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8523
_exptl_absorpt_correction_T_max  0.9837
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15767
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.21
_diffrn_reflns_theta_max         25.68
_reflns_number_total             3095
_reflns_number_gt                2905
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0421P)²+0.9793P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.14(9)
_refine_ls_number_reflns         3095
_refine_ls_number_parameters     217
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.0828
_refine_ls_wR_factor_gt          0.0811
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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
S1 S 0.39776(3) -0.0425(3) 0.99861(7) 0.0259(2) Uani 1 1 d . . .
S2 S 0.38808(3) 0.2639(2) 0.80390(7) 0.0206(2) Uani 1 1 d . . .
S3 S 0.47325(3) 0.0613(2) 0.87253(6) 0.02059(19) Uani 1 1 d . . .
S4 S 0.41949(3) 0.1931(3) 0.38219(8) 0.0305(2) Uani 1 1 d . . .
S5 S 0.32525(3) 0.0751(2) 0.35947(7) 0.0231(2) Uani 1 1 d . . .
S6 S 0.37424(3) 0.3952(2) 0.20425(6) 0.0231(2) Uani 1 1 d . . .
N1 N 0.35126(11) 0.6902(9) 0.5779(3) 0.0338(8) Uani 1 1 d . . .
N2 N 0.21053(11) -0.2051(9) 0.3787(3) 0.0375(8) Uani 1 1 d . . .
C1 C 0.41851(11) 0.0871(8) 0.8972(2) 0.0195(7) Uani 1 1 d . . .
C2 C 0.43102(10) 0.3456(9) 0.7259(3) 0.0170(7) Uani 1 1 d . . .
C3 C 0.47186(11) 0.2501(9) 0.7580(2) 0.0181(7) Uani 1 1 d . . .
C4 C 0.50840(11) 0.3051(9) 0.7020(3) 0.0212(7) Uani 1 1 d . . .
H4 H 0.5361 0.2331 0.7238 0.025 Uiso 1 1 calc R . .
C5 C 0.50361(12) 0.4675(10) 0.6137(3) 0.0227(8) Uani 1 1 d . . .
H5 H 0.5284 0.5118 0.5753 0.027 Uiso 1 1 calc R . .
C6 C 0.46350(12) 0.5652(9) 0.5808(3) 0.0229(8) Uani 1 1 d . . .
H6 H 0.4608 0.6748 0.5200 0.027 Uiso 1 1 calc R . .
C7 C 0.42655(11) 0.5044(9) 0.6365(3) 0.0185(7) Uani 1 1 d . . .
C8 C 0.38480(13) 0.6068(9) 0.6023(3) 0.0242(8) Uani 1 1 d . . .
C9 C 0.37511(12) 0.2209(9) 0.3189(3) 0.0235(8) Uani 1 1 d . . .
C11 C 0.31959(11) 0.3285(9) 0.1809(2) 0.0178(7) Uani 1 1 d . . .
C10 C 0.29640(12) 0.1758(9) 0.2557(2) 0.0203(8) Uani 1 1 d . . .
C12 C 0.29947(12) 0.4197(9) 0.0947(3) 0.0240(8) Uani 1 1 d . . .
H12 H 0.3154 0.5248 0.0441 0.029 Uiso 1 1 calc R . .
C13 C 0.25585(12) 0.3533(10) 0.0848(3) 0.0242(8) Uani 1 1 d . . .
H13 H 0.2417 0.4156 0.0267 0.029 Uiso 1 1 calc R . .
C14 C 0.23239(12) 0.1986(9) 0.1574(3) 0.0247(8) Uani 1 1 d . . .
H14 H 0.2024 0.1546 0.1487 0.030 Uiso 1 1 calc R . .
C15 C 0.25241(12) 0.1067(9) 0.2431(3) 0.0211(8) Uani 1 1 d . . .
C16 C 0.22863(12) -0.0646(10) 0.3186(3) 0.0256(8) 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 C1 1.628(4) . ?
S2 C1 1.742(4) . ?
S2 C2 1.744(3) . ?
S3 C1 1.731(4) . ?
S3 C3 1.752(4) . ?
S4 C9 1.635(4) . ?
S5 C9 1.736(4) . ?
S5 C10 1.741(4) . ?
S6 C9 1.731(4) . ?
S6 C11 1.740(3) . ?
N1 C8 1.138(5) . ?
N2 C16 1.143(5) . ?
C2 C3 1.389(5) . ?
C2 C7 1.393(5) . ?
C3 C4 1.389(5) . ?
C4 C5 1.386(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.375(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.401(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.432(5) . ?
C11 C10 1.393(5) . ?
C11 C12 1.396(5) . ?
C10 C15 1.397(5) . ?
C12 C13 1.380(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.379(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.390(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.441(5) . ?

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 S2 C2 97.03(17) . . ?
C1 S3 C3 97.61(17) . . ?
C9 S5 C10 96.53(18) . . ?
C9 S6 C11 97.45(17) . . ?
S1 C1 S3 122.7(2) . . ?
S1 C1 S2 123.5(2) . . ?
S3 C1 S2 113.8(2) . . ?
C3 C2 C7 119.6(3) . . ?
C3 C2 S2 116.4(3) . . ?
C7 C2 S2 124.0(3) . . ?
C4 C3 C2 121.3(3) . . ?
C4 C3 S3 123.6(3) . . ?
C2 C3 S3 115.1(3) . . ?
C5 C4 C3 118.6(3) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C6 C5 C4 121.0(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 120.5(4) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C2 C7 C6 119.1(3) . . ?
C2 C7 C8 120.5(3) . . ?
C6 C7 C8 120.4(3) . . ?
N1 C8 C7 177.9(4) . . ?
S4 C9 S6 122.3(2) . . ?
S4 C9 S5 123.4(2) . . ?
S6 C9 S5 114.3(2) . . ?
C10 C11 C12 121.2(3) . . ?
C10 C11 S6 115.0(3) . . ?
C12 C11 S6 123.8(3) . . ?
C11 C10 C15 119.2(3) . . ?
C11 C10 S5 116.7(3) . . ?
C15 C10 S5 124.1(3) . . ?
C13 C12 C11 118.4(3) . . ?
C13 C12 H12 120.8 . . ?
C11 C12 H12 120.8 . . ?
C14 C13 C12 121.4(3) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C15 120.3(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C10 119.5(3) . . ?
C14 C15 C16 120.9(3) . . ?
C10 C15 C16 119.6(3) . . ?
N2 C16 C15 178.5(4) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.68
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.679
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.092
####################################################################### 
# 
# 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_GL57I3-C2C
_database_code_depnum_ccdc_archive 'CCDC 1879084'
_audit_update_record             
;
2018-11-14 deposited with the CCDC.
2018-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H6 I3 N S6'
_chemical_formula_weight         749.25

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'
I I -0.4742 1.8119 '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           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   9.4744(11)
_cell_length_b                   15.4187(17)
_cell_length_c                   26.876(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.640(7)
_cell_angle_gamma                90.00
_cell_volume                     3924.6(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3959
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      26.99

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.536
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2768
_exptl_absorpt_coefficient_mu    5.413
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6128
_exptl_absorpt_correction_T_max  0.8121
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13448
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_sigmaI/netI    0.0500
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.91
_diffrn_reflns_theta_max         25.68
_reflns_number_total             3686
_reflns_number_gt                3047
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0001P)²+65.0662P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3686
_refine_ls_number_parameters     238
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.1467
_refine_ls_R_factor_gt           0.1289
_refine_ls_wR_factor_ref         0.2832
_refine_ls_wR_factor_gt          0.2770
_refine_ls_goodness_of_fit_ref   1.199
_refine_ls_restrained_S_all      1.195
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

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
I001 I 0.7500 0.7500 0.5000 0.0243(5) Uani 1 2 d S . .
I002 I 0.7423(3) 0.89256(11) 0.42971(7) 0.0499(6) Uani 1 1 d . . .
S2 S 0.0771(7) 0.4818(5) 0.6020(3) 0.0437(19) Uani 1 1 d . . .
S4 S 0.0979(8) 0.5954(4) 0.5149(2) 0.0389(17) Uani 1 1 d . . .
S5 S 0.3956(9) 0.7199(5) 0.4186(3) 0.052(2) Uani 1 1 d . B .
S3 S 0.4036(9) 0.5960(5) 0.5145(3) 0.051(2) Uani 1 1 d . . .
S6 S 0.0910(9) 0.7220(5) 0.4188(3) 0.055(2) Uani 1 1 d . A .
S1 S 0.4446(9) 0.4842(6) 0.6016(4) 0.076(4) Uani 1 1 d . . .
C6 C 0.239(3) 0.6844(13) 0.4445(8) 0.032(6) Uani 1 1 d . . .
C7 C 0.313(3) 0.7716(16) 0.3700(9) 0.030(5) Uani 1 1 d U . .
C8 C 0.170(3) 0.7756(18) 0.3679(9) 0.043(7) Uani 1 1 d . A .
C4 C 0.186(3) 0.5345(15) 0.5616(8) 0.031(6) Uani 1 1 d . B .
C9 C 0.385(4) 0.8114(18) 0.3310(11) 0.053(9) Uani 1 1 d . A .
C3 C 0.326(2) 0.5358(13) 0.5609(8) 0.024(5) Uani 1 1 d . B .
C10 C 0.093(3) 0.819(3) 0.3300(14) 0.077(14) Uani 1 1 d . . .
C11 C 0.303(4) 0.8487(16) 0.2928(9) 0.047(8) Uani 1 1 d . . .
H11 H 0.3492 0.8724 0.2650 0.056 Uiso 1 1 calc R A .
C12 C 0.171(5) 0.852(3) 0.2934(13) 0.087(16) Uani 1 1 d . A .
H12 H 0.1223 0.8806 0.2665 0.105 Uiso 1 1 calc R . .
C13 C 0.511(4) 0.787(3) 0.3208(15) 0.029(10) Uani 0.58(4) 1 d P A 1
N1 N 0.620(5) 0.774(3) 0.3193(17) 0.052(13) Uiso 0.58(4) 1 d P A 1
C13A C -0.057(6) 0.787(4) 0.323(2) 0.027(13) Uiso 0.42(4) 1 d P A 2
N1A N -0.161(6) 0.776(3) 0.3191(19) 0.039(14) Uiso 0.42(4) 1 d P A 2
C5 C 0.248(4) 0.6297(14) 0.4875(8) 0.045(8) Uani 1 1 d . B .
I3 I 0.0000 0.5659(2) 0.2500 0.079(2) Uani 0.782(10) 2 d SP . 1
I4 I 0.2852(9) 0.5556(2) 0.30468(14) 0.0833(19) Uani 0.782(10) 1 d P . 1
I3A I 0.5000 0.5662(11) 0.2500 0.20(2) Uani 0.218(10) 2 d SP . 2
I4A I 0.2177(10) 0.5643(8) 0.3040(4) 0.032(3) Uani 0.218(10) 1 d PU . 2
C1 C 0.333(3) 0.439(2) 0.6477(12) 0.021(9) Uani 0.68(6) 1 d PU B 1
H1A H 0.3877 0.3976 0.6685 0.025 Uiso 0.68(6) 1 calc PR B 1
H1B H 0.3001 0.4864 0.6696 0.025 Uiso 0.68(6) 1 calc PR B 1
C2 C 0.215(4) 0.397(3) 0.6258(15) 0.039(11) Uani 0.68(6) 1 d PU B 1
H2A H 0.1713 0.3584 0.6506 0.046 Uiso 0.68(6) 1 calc PR B 1
H2B H 0.2451 0.3605 0.5977 0.046 Uiso 0.68(6) 1 calc PR B 1
C2A C 0.206(8) 0.443(5) 0.648(3) 0.03(2) Uiso 0.32(6) 1 d P B 2
H2A1 H 0.2409 0.4927 0.6681 0.036 Uiso 0.32(6) 1 calc PR B 2
H2A2 H 0.1607 0.4013 0.6701 0.036 Uiso 0.32(6) 1 calc PR B 2
C1A C 0.321(6) 0.403(4) 0.625(2) 0.006(15) Uiso 0.32(6) 1 d P B 2
H1A1 H 0.2854 0.3669 0.5964 0.007 Uiso 0.32(6) 1 calc PR B 2
H1A2 H 0.3706 0.3644 0.6487 0.007 Uiso 0.32(6) 1 calc PR B 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
I001 I002 2.8979(17) . ?
I001 I002 2.8979(17) 7_666 ?
S2 C4 1.72(3) . ?
S2 C2A 1.81(8) . ?
S2 C2 1.94(4) . ?
S4 C5 1.71(3) . ?
S4 C4 1.76(2) . ?
S5 C7 1.70(2) . ?
S5 C6 1.74(3) . ?
S3 C5 1.70(3) . ?
S3 C3 1.74(2) . ?
S6 C6 1.65(3) . ?
S6 C8 1.78(2) . ?
S1 C3 1.74(2) . ?
S1 C1A 1.83(5) . ?
S1 C1 1.79(3) . ?
C6 C5 1.43(3) . ?
C7 C8 1.35(4) . ?
C7 C9 1.41(4) . ?
C8 C10 1.40(4) . ?
C4 C3 1.33(4) . ?
C9 C13 1.29(5) . ?
C9 C11 1.40(4) . ?
C10 C12 1.35(5) . ?
C10 C13A 1.51(6) . ?
C11 C12 1.26(5) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 N1 1.05(6) . ?
C13A N1A 1.01(7) . ?
I3 I4 3.043(8) 2 ?
I3 I4 3.043(8) . ?
I3A I4A 3.079(10) 2_655 ?
I3A I4A 3.079(10) . ?
C1 C2 1.41(6) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2A C1A 1.41(10) . ?
C2A H2A1 0.9900 . ?
C2A H2A2 0.9900 . ?
C1A H1A1 0.9900 . ?
C1A H1A2 0.9900 . ?

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
I002 I001 I002 180.000(1) . 7_666 ?
C4 S2 C2A 100(3) . . ?
C4 S2 C2 96.8(16) . . ?
C2A S2 C2 28(3) . . ?
C5 S4 C4 95.2(13) . . ?
C7 S5 C6 94.3(12) . . ?
C5 S3 C3 95.0(13) . . ?
C6 S6 C8 96.5(13) . . ?
C3 S1 C1A 96.6(19) . . ?
C3 S1 C1 103.0(13) . . ?
C1A S1 C1 26.8(17) . . ?
C5 C6 S6 125(2) . . ?
C5 C6 S5 118(2) . . ?
S6 C6 S5 116.4(13) . . ?
C8 C7 C9 117(2) . . ?
C8 C7 S5 119.4(19) . . ?
C9 C7 S5 123(2) . . ?
C7 C8 C10 123(2) . . ?
C7 C8 S6 112.9(19) . . ?
C10 C8 S6 124(2) . . ?
C3 C4 S2 129.2(19) . . ?
C3 C4 S4 115.7(18) . . ?
S2 C4 S4 115.1(16) . . ?
C13 C9 C11 118(3) . . ?
C13 C9 C7 121(3) . . ?
C11 C9 C7 117(3) . . ?
C4 C3 S3 117.7(18) . . ?
C4 C3 S1 127.9(17) . . ?
S3 C3 S1 114.4(13) . . ?
C12 C10 C8 115(3) . . ?
C12 C10 C13A 124(4) . . ?
C8 C10 C13A 114(3) . . ?
C12 C11 C9 123(3) . . ?
C12 C11 H11 118.4 . . ?
C9 C11 H11 118.4 . . ?
C11 C12 C10 124(3) . . ?
C11 C12 H12 118.1 . . ?
C10 C12 H12 118.1 . . ?
N1 C13 C9 168(5) . . ?
N1A C13A C10 170(7) . . ?
C6 C5 S3 124(3) . . ?
C6 C5 S4 120(2) . . ?
S3 C5 S4 116.4(13) . . ?
I4 I3 I4 174.06(18) 2 . ?
I4A I3A I4A 178.9(8) 2_655 . ?
C2 C1 S1 112(3) . . ?
C2 C1 H1A 109.3 . . ?
S1 C1 H1A 109.3 . . ?
C2 C1 H1B 109.3 . . ?
S1 C1 H1B 109.3 . . ?
H1A C1 H1B 107.9 . . ?
C1 C2 S2 110(3) . . ?
C1 C2 H2A 109.7 . . ?
S2 C2 H2A 109.7 . . ?
C1 C2 H2B 109.7 . . ?
S2 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
C1A C2A S2 111(5) . . ?
C1A C2A H2A1 109.4 . . ?
S2 C2A H2A1 109.4 . . ?
C1A C2A H2A2 109.4 . . ?
S2 C2A H2A2 109.4 . . ?
H2A1 C2A H2A2 108.0 . . ?
C2A C1A S1 111(5) . . ?
C2A C1A H1A1 109.5 . . ?
S1 C1A H1A1 109.5 . . ?
C2A C1A H1A2 109.5 . . ?
S1 C1A H1A2 109.5 . . ?
H1A1 C1A H1A2 108.1 . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.68
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         3.461
_refine_diff_density_min         -3.070
_refine_diff_density_rms         0.395
####################################################################### 
# 
# 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_SRA5
_database_code_depnum_ccdc_archive 'CCDC 1879085'
_audit_update_record             
;
2018-11-14 deposited with the CCDC.
2018-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H7 N S6'
_chemical_formula_weight         369.56

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pca2(1)

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

_cell_length_a                   14.1394(6)
_cell_length_b                   4.06500(10)
_cell_length_c                   24.6729(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1418.12(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4326
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      27.13

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.731
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8328
_exptl_absorpt_correction_T_max  0.9813
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10080
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_sigmaI/netI    0.0488
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         25.68
_reflns_number_total             2660
_reflns_number_gt                2458
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0461P)²+0.0000P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(10)
_refine_ls_number_reflns         2660
_refine_ls_number_parameters     181
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0829
_refine_ls_wR_factor_gt          0.0812
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.30985(6) 0.0966(2) 0.30605(3) 0.0223(2) Uani 1 1 d . . .
S2 S 0.13348(6) 0.4383(2) 0.39045(3) 0.0203(2) Uani 1 1 d . . .
S3 S 0.42413(6) 0.0867(2) 0.40505(3) 0.0216(2) Uani 1 1 d . . .
S4 S 0.28082(6) 0.40768(19) 0.47462(3) 0.0200(2) Uani 1 1 d . . .
S5 S 0.57150(6) 0.08072(19) 0.50661(3) 0.0198(2) Uani 1 1 d . . .
S6 S 0.42605(6) 0.4171(2) 0.57415(3) 0.0203(2) Uani 1 1 d . . .
N1 N 0.4357(2) 0.7638(8) 0.71400(13) 0.0311(7) Uani 1 1 d . . .
C1 C 0.2007(2) 0.2954(9) 0.28671(13) 0.0205(7) Uani 1 1 d . . .
H1A H 0.2120 0.5351 0.2838 0.025 Uiso 1 1 calc R . .
H1B H 0.1818 0.2148 0.2504 0.025 Uiso 1 1 calc R . .
C2 C 0.1198(2) 0.2377(8) 0.32579(13) 0.0195(7) Uani 1 1 d . . .
H2A H 0.1133 -0.0019 0.3319 0.023 Uiso 1 1 calc R . .
H2B H 0.0605 0.3160 0.3088 0.023 Uiso 1 1 calc R . .
C3 C 0.3152(2) 0.1923(8) 0.37527(13) 0.0180(7) Uani 1 1 d . . .
C4 C 0.2494(2) 0.3257(8) 0.40648(13) 0.0179(7) Uani 1 1 d . . .
C5 C 0.3962(2) 0.2511(8) 0.46893(13) 0.0173(7) Uani 1 1 d . . .
C6 C 0.4574(2) 0.2525(8) 0.51008(13) 0.0182(7) Uani 1 1 d . . .
C7 C 0.5362(2) 0.3518(8) 0.60383(14) 0.0172(7) Uani 1 1 d . . .
C8 C 0.6049(2) 0.1968(8) 0.57224(13) 0.0172(7) Uani 1 1 d . . .
C9 C 0.6945(2) 0.1312(8) 0.59366(14) 0.0190(8) Uani 1 1 d . . .
H9 H 0.7409 0.0232 0.5723 0.023 Uiso 1 1 calc R . .
C10 C 0.7151(3) 0.2253(9) 0.64644(14) 0.0264(8) Uani 1 1 d . . .
H10 H 0.7761 0.1820 0.6609 0.032 Uiso 1 1 calc R . .
C11 C 0.6488(3) 0.3795(8) 0.67798(14) 0.0229(8) Uani 1 1 d . . .
H11 H 0.6637 0.4393 0.7142 0.028 Uiso 1 1 calc R . .
C12 C 0.5590(3) 0.4489(8) 0.65676(14) 0.0193(8) Uani 1 1 d . . .
C13 C 0.4900(2) 0.6211(8) 0.68858(14) 0.0197(7) 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 C3 1.753(3) . ?
S1 C1 1.807(3) . ?
S2 C4 1.747(3) . ?
S2 C2 1.802(3) . ?
S3 C5 1.757(3) . ?
S3 C3 1.760(3) . ?
S4 C5 1.757(3) . ?
S4 C4 1.770(3) . ?
S5 C8 1.752(3) . ?
S5 C6 1.760(3) . ?
S6 C7 1.742(3) . ?
S6 C6 1.773(3) . ?
N1 C13 1.149(4) . ?
C1 C2 1.514(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.324(5) . ?
C5 C6 1.334(4) . ?
C7 C8 1.395(5) . ?
C7 C12 1.402(5) . ?
C8 C9 1.399(4) . ?
C9 C10 1.388(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.370(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.402(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.435(5) . ?

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
C3 S1 C1 101.25(16) . . ?
C4 S2 C2 100.51(15) . . ?
C5 S3 C3 94.88(15) . . ?
C5 S4 C4 95.11(16) . . ?
C8 S5 C6 95.45(15) . . ?
C7 S6 C6 95.39(16) . . ?
C2 C1 S1 114.1(2) . . ?
C2 C1 H1A 108.7 . . ?
S1 C1 H1A 108.7 . . ?
C2 C1 H1B 108.7 . . ?
S1 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
C1 C2 S2 114.4(2) . . ?
C1 C2 H2A 108.7 . . ?
S2 C2 H2A 108.7 . . ?
C1 C2 H2B 108.7 . . ?
S2 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
C4 C3 S1 128.8(3) . . ?
C4 C3 S3 118.2(2) . . ?
S1 C3 S3 112.99(19) . . ?
C3 C4 S2 129.4(3) . . ?
C3 C4 S4 116.9(3) . . ?
S2 C4 S4 113.65(19) . . ?
C6 C5 S3 122.6(2) . . ?
C6 C5 S4 122.7(2) . . ?
S3 C5 S4 114.72(18) . . ?
C5 C6 S5 123.8(2) . . ?
C5 C6 S6 121.2(2) . . ?
S5 C6 S6 114.97(18) . . ?
C8 C7 C12 119.2(3) . . ?
C8 C7 S6 117.1(3) . . ?
C12 C7 S6 123.7(3) . . ?
C7 C8 C9 120.3(3) . . ?
C7 C8 S5 116.8(3) . . ?
C9 C8 S5 122.8(3) . . ?
C10 C9 C8 119.4(3) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C11 C10 C9 121.1(3) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 120.0(3) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C7 120.0(3) . . ?
C11 C12 C13 120.6(3) . . ?
C7 C12 C13 119.4(3) . . ?
N1 C13 C12 178.8(4) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.68
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.072
####################################################################### 
# 
# 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_GL55F9_19
_database_code_depnum_ccdc_archive 'CCDC 1879086'
_audit_update_record             
;
2018-11-14 deposited with the CCDC.
2018-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H14 N2 S12'
_chemical_formula_weight         739.11

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'

_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                   7.7442(5)
_cell_length_b                   7.7440(5)
_cell_length_c                   26.3522(16)
_cell_angle_alpha                81.877(2)
_cell_angle_beta                 83.912(2)
_cell_angle_gamma                65.730(2)
_cell_volume                     1424.22(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1434
_cell_measurement_theta_min      3.12
_cell_measurement_theta_max      26.16

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6493
_exptl_absorpt_correction_T_max  0.9632
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9574
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_sigmaI/netI    0.0717
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         25.35
_reflns_number_total             5002
_reflns_number_gt                3670
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0439P)²+0.0000P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5002
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1023
_refine_ls_wR_factor_gt          0.0937
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_restrained_S_all      0.976
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.50067(15) 0.66161(17) 0.12900(4) 0.0269(3) Uani 1 1 d . . .
S2 S 0.08129(14) 0.70772(15) 0.20819(4) 0.0239(3) Uani 1 1 d . . .
S3 S 0.27742(14) 0.69903(16) 0.04501(4) 0.0244(3) Uani 1 1 d . . .
S4 S -0.07715(14) 0.73643(16) 0.11082(4) 0.0233(3) Uani 1 1 d . . .
S5 S 0.07817(14) 0.74818(16) -0.05555(4) 0.0240(3) Uani 1 1 d . . .
S6 S -0.28383(14) 0.77963(15) 0.00650(4) 0.0223(3) Uani 1 1 d . . .
S7 S 0.63932(14) 0.49050(15) 0.32362(4) 0.0219(2) Uani 1 1 d . . .
S8 S 1.04310(13) 0.31517(14) 0.39170(3) 0.0166(2) Uani 1 1 d . . .
S9 S 0.45066(13) 0.38111(13) 0.41849(3) 0.0148(2) Uani 1 1 d . . .
S10 S 0.78976(12) 0.23679(13) 0.47553(3) 0.0142(2) Uani 1 1 d . . .
S11 S 0.21027(12) 0.26560(13) 0.51701(3) 0.0141(2) Uani 1 1 d . . .
S12 S 0.55125(13) 0.12487(13) 0.57375(3) 0.0140(2) Uani 1 1 d . . .
N1 N 0.2111(5) 0.7689(5) -0.19750(12) 0.0266(8) Uani 1 1 d . . .
N2 N 0.6204(5) -0.0583(5) 0.71021(12) 0.0288(9) Uani 1 1 d . . .
C1 C 0.4521(6) 0.6834(6) 0.19761(14) 0.0222(9) Uani 1 1 d . . .
H1A H 0.5741 0.6272 0.2146 0.027 Uiso 1 1 calc R . .
H1B H 0.3919 0.8203 0.2027 0.027 Uiso 1 1 calc R . .
C2 C 0.3241(5) 0.5872(6) 0.22364(14) 0.0230(9) Uani 1 1 d . . .
H2B H 0.3313 0.5774 0.2613 0.028 Uiso 1 1 calc R . .
H2A H 0.3730 0.4561 0.2138 0.028 Uiso 1 1 calc R . .
C3 C 0.2792(5) 0.6966(5) 0.11153(13) 0.0141(8) Uani 1 1 d . . .
C4 C 0.1187(5) 0.7127(5) 0.14113(14) 0.0150(8) Uani 1 1 d . . .
C5 C 0.0385(5) 0.7316(5) 0.04807(14) 0.0181(9) Uani 1 1 d . . .
C6 C -0.0466(5) 0.7509(5) 0.00573(14) 0.0170(9) Uani 1 1 d . . .
C7 C -0.1128(5) 0.7795(5) -0.08910(13) 0.0137(8) Uani 1 1 d . . .
C8 C -0.2819(5) 0.7910(5) -0.06005(14) 0.0172(9) Uani 1 1 d . . .
C9 C -0.1002(5) 0.7875(5) -0.14264(14) 0.0164(8) Uani 1 1 d . . .
C10 C -0.4364(6) 0.8110(5) -0.08441(15) 0.0217(9) Uani 1 1 d . . .
H10 H -0.5504 0.8196 -0.0654 0.026 Uiso 1 1 calc R . .
C11 C -0.2568(5) 0.8065(5) -0.16691(14) 0.0209(9) Uani 1 1 d . . .
H11 H -0.2529 0.8115 -0.2032 0.025 Uiso 1 1 calc R . .
C12 C -0.4241(6) 0.8187(5) -0.13716(15) 0.0239(10) Uani 1 1 d . . .
H12 H -0.5319 0.8326 -0.1542 0.029 Uiso 1 1 calc R . .
C13 C 0.0747(6) 0.7773(5) -0.17279(14) 0.0190(9) Uani 1 1 d . . .
C14 C 1.0095(5) 0.4448(5) 0.33031(13) 0.0155(8) Uani 1 1 d . . .
H14A H 0.9508 0.5827 0.3343 0.019 Uiso 1 1 calc R . .
H14B H 1.1348 0.4168 0.3119 0.019 Uiso 1 1 calc R . .
C15 C 0.8868(5) 0.3998(5) 0.29844(13) 0.0180(9) Uani 1 1 d . . .
H15A H 0.9354 0.2601 0.2981 0.022 Uiso 1 1 calc R . .
H15B H 0.8932 0.4575 0.2627 0.022 Uiso 1 1 calc R . .
C16 C 0.8121(5) 0.3309(5) 0.41276(13) 0.0113(8) Uani 1 1 d . . .
C17 C 0.6594(5) 0.3963(5) 0.38680(13) 0.0126(8) Uani 1 1 d . . .
C18 C 0.5498(5) 0.2761(5) 0.47592(13) 0.0114(8) Uani 1 1 d . . .
C19 C 0.4489(5) 0.2306(5) 0.51670(13) 0.0112(8) Uani 1 1 d . . .
C20 C 0.3436(5) 0.1153(5) 0.60708(13) 0.0118(8) Uani 1 1 d . . .
C21 C 0.1848(5) 0.1773(5) 0.57997(13) 0.0117(8) Uani 1 1 d . . .
C22 C 0.3313(5) 0.0460(5) 0.65791(13) 0.0125(8) Uani 1 1 d . . .
C23 C 0.0148(5) 0.1681(5) 0.60345(14) 0.0137(8) Uani 1 1 d . . .
H23 H -0.0947 0.2131 0.5840 0.016 Uiso 1 1 calc R . .
C24 C 0.1630(5) 0.0350(5) 0.68141(14) 0.0144(8) Uani 1 1 d . . .
H24 H 0.1594 -0.0144 0.7164 0.017 Uiso 1 1 calc R . .
C25 C 0.0061(5) 0.0954(5) 0.65368(14) 0.0160(8) Uani 1 1 d . . .
H25 H -0.1075 0.0872 0.6689 0.019 Uiso 1 1 calc R . .
C26 C 0.4936(6) -0.0140(5) 0.68706(14) 0.0181(9) 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 C3 1.726(4) . ?
S1 C1 1.824(4) . ?
S2 C4 1.758(4) . ?
S2 C2 1.784(4) . ?
S3 C3 1.752(3) . ?
S3 C5 1.756(4) . ?
S4 C4 1.720(4) . ?
S4 C5 1.792(4) . ?
S5 C7 1.717(4) . ?
S5 C6 1.790(4) . ?
S6 C8 1.742(4) . ?
S6 C6 1.756(4) . ?
S7 C17 1.717(3) . ?
S7 C15 1.834(4) . ?
S8 C14 1.763(3) . ?
S8 C16 1.775(4) . ?
S9 C18 1.711(3) . ?
S9 C17 1.780(4) . ?
S10 C16 1.732(3) . ?
S10 C18 1.754(4) . ?
S11 C21 1.726(3) . ?
S11 C19 1.753(4) . ?
S12 C19 1.712(3) . ?
S12 C20 1.773(4) . ?
N1 C13 1.164(5) . ?
N2 C26 1.116(5) . ?
C1 C2 1.526(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2B 0.9900 . ?
C2 H2A 0.9900 . ?
C3 C4 1.364(5) . ?
C5 C6 1.315(5) . ?
C7 C9 1.398(5) . ?
C7 C8 1.421(5) . ?
C8 C10 1.360(5) . ?
C9 C11 1.376(5) . ?
C9 C13 1.474(5) . ?
C10 C12 1.378(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.416(5) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C14 C15 1.501(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.305(5) . ?
C18 C19 1.353(5) . ?
C20 C21 1.363(5) . ?
C20 C22 1.380(5) . ?
C21 C23 1.419(5) . ?
C22 C24 1.412(5) . ?
C22 C26 1.417(5) . ?
C23 C25 1.369(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.362(5) . ?
C24 H24 0.9500 . ?
C25 H25 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
C3 S1 C1 100.14(17) . . ?
C4 S2 C2 97.26(17) . . ?
C3 S3 C5 92.86(17) . . ?
C4 S4 C5 93.68(18) . . ?
C7 S5 C6 93.97(17) . . ?
C8 S6 C6 93.34(17) . . ?
C17 S7 C15 102.53(16) . . ?
C14 S8 C16 103.27(17) . . ?
C18 S9 C17 95.82(17) . . ?
C16 S10 C18 97.48(16) . . ?
C21 S11 C19 98.12(16) . . ?
C19 S12 C20 96.12(17) . . ?
C2 C1 S1 114.2(3) . . ?
C2 C1 H1A 108.7 . . ?
S1 C1 H1A 108.7 . . ?
C2 C1 H1B 108.7 . . ?
S1 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
C1 C2 S2 114.4(3) . . ?
C1 C2 H2B 108.7 . . ?
S2 C2 H2B 108.7 . . ?
C1 C2 H2A 108.7 . . ?
S2 C2 H2A 108.7 . . ?
H2B C2 H2A 107.6 . . ?
C4 C3 S1 130.2(3) . . ?
C4 C3 S3 119.0(3) . . ?
S1 C3 S3 110.8(2) . . ?
C3 C4 S4 117.9(3) . . ?
C3 C4 S2 129.0(3) . . ?
S4 C4 S2 113.1(2) . . ?
C6 C5 S3 120.1(3) . . ?
C6 C5 S4 123.3(3) . . ?
S3 C5 S4 116.5(2) . . ?
C5 C6 S6 122.2(3) . . ?
C5 C6 S5 120.5(3) . . ?
S6 C6 S5 117.3(2) . . ?
C9 C7 C8 121.5(3) . . ?
C9 C7 S5 121.3(3) . . ?
C8 C7 S5 117.2(3) . . ?
C10 C8 C7 119.9(3) . . ?
C10 C8 S6 122.0(3) . . ?
C7 C8 S6 118.2(3) . . ?
C11 C9 C7 118.2(3) . . ?
C11 C9 C13 120.3(3) . . ?
C7 C9 C13 121.5(3) . . ?
C8 C10 C12 118.7(4) . . ?
C8 C10 H10 120.7 . . ?
C12 C10 H10 120.7 . . ?
C9 C11 C12 119.3(4) . . ?
C9 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C10 C12 C11 122.5(4) . . ?
C10 C12 H12 118.8 . . ?
C11 C12 H12 118.8 . . ?
N1 C13 C9 178.6(4) . . ?
C15 C14 S8 113.3(2) . . ?
C15 C14 H14A 108.9 . . ?
S8 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
S8 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C14 C15 S7 111.5(3) . . ?
C14 C15 H15A 109.3 . . ?
S7 C15 H15A 109.3 . . ?
C14 C15 H15B 109.3 . . ?
S7 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
C17 C16 S10 115.8(3) . . ?
C17 C16 S8 128.9(3) . . ?
S10 C16 S8 115.29(19) . . ?
C16 C17 S7 126.6(3) . . ?
C16 C17 S9 117.9(3) . . ?
S7 C17 S9 115.5(2) . . ?
C19 C18 S9 122.0(3) . . ?
C19 C18 S10 125.0(3) . . ?
S9 C18 S10 113.05(19) . . ?
C18 C19 S12 121.2(3) . . ?
C18 C19 S11 125.2(3) . . ?
S12 C19 S11 113.61(19) . . ?
C21 C20 C22 117.5(3) . . ?
C21 C20 S12 117.3(3) . . ?
C22 C20 S12 125.2(3) . . ?
C20 C21 C23 120.7(3) . . ?
C20 C21 S11 114.7(3) . . ?
C23 C21 S11 124.6(3) . . ?
C20 C22 C24 122.1(3) . . ?
C20 C22 C26 118.2(3) . . ?
C24 C22 C26 119.7(3) . . ?
C25 C23 C21 121.1(3) . . ?
C25 C23 H23 119.5 . . ?
C21 C23 H23 119.5 . . ?
C25 C24 C22 119.8(3) . . ?
C25 C24 H24 120.1 . . ?
C22 C24 H24 120.1 . . ?
C24 C25 C23 118.8(3) . . ?
C24 C25 H25 120.6 . . ?
C23 C25 H25 120.6 . . ?
N2 C26 C22 178.9(4) . . ?

_diffrn_measured_fraction_theta_max 0.958
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.958
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.093
####################################################################### 
# 
# 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_SRA4
_database_code_depnum_ccdc_archive 'CCDC 1879087'
_audit_update_record             
;
2018-11-14 deposited with the CCDC.
2018-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H3 N O S2'
_chemical_formula_sum            'C8 H3 N O S2'
_chemical_formula_weight         193.23

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   3.8349(2)
_cell_length_b                   14.8206(6)
_cell_length_c                   13.7718(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.231(2)
_cell_angle_gamma                90.00
_cell_volume                     782.13(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1592
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      26.78

_exptl_crystal_description       needle
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             392
_exptl_absorpt_coefficient_mu    0.619
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9184
_exptl_absorpt_correction_T_max  0.9638
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(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 APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4515
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_sigmaI/netI    0.0476
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.12
_diffrn_reflns_theta_max         25.67
_reflns_number_total             1479
_reflns_number_gt                1181
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0485P)²+1.1451P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1479
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_ref         0.1222
_refine_ls_wR_factor_gt          0.1152
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.3720(2) 0.09983(6) 0.27556(6) 0.0245(3) Uani 1 1 d . . .
S2 S 0.0823(2) 0.15497(6) 0.46422(6) 0.0237(3) Uani 1 1 d . . .
O1 O 0.2236(7) -0.01249(16) 0.41423(18) 0.0336(6) Uani 1 1 d . . .
N1 N -0.1635(9) 0.3751(2) 0.5630(2) 0.0363(8) Uani 1 1 d . . .
C1 C 0.3021(9) 0.3685(2) 0.2411(3) 0.0293(8) Uani 1 1 d . . .
H1 H 0.3470 0.4127 0.1932 0.035 Uiso 1 1 calc R . .
C2 C 0.3698(8) 0.2793(2) 0.2215(2) 0.0266(8) Uani 1 1 d . . .
H2 H 0.4614 0.2621 0.1611 0.032 Uiso 1 1 calc R . .
C3 C 0.3013(8) 0.2144(2) 0.2920(2) 0.0225(7) Uani 1 1 d . . .
C4 C 0.2270(9) 0.0651(2) 0.3893(2) 0.0248(7) Uani 1 1 d . . .
C5 C 0.1664(8) 0.2401(2) 0.3810(2) 0.0202(7) Uani 1 1 d . . .
C6 C 0.1007(8) 0.3312(2) 0.3990(2) 0.0237(7) Uani 1 1 d . . .
C7 C 0.1699(9) 0.3957(2) 0.3290(3) 0.0289(8) Uani 1 1 d . . .
H3 H 0.1272 0.4577 0.3411 0.035 Uiso 1 1 calc R . .
C8 C -0.0447(9) 0.3565(2) 0.4909(3) 0.0256(7) 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 C3 1.736(3) . ?
S1 C4 1.759(3) . ?
S2 C5 1.743(3) . ?
S2 C4 1.787(3) . ?
O1 C4 1.200(4) . ?
N1 C8 1.143(5) . ?
C1 C2 1.375(5) . ?
C1 C7 1.391(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.399(5) . ?
C2 H2 0.9500 . ?
C3 C5 1.401(4) . ?
C5 C6 1.398(5) . ?
C6 C7 1.390(5) . ?
C6 C8 1.451(5) . ?
C7 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
C3 S1 C4 96.53(16) . . ?
C5 S2 C4 95.15(16) . . ?
C2 C1 C7 121.8(3) . . ?
C2 C1 H1 119.1 . . ?
C7 C1 H1 119.1 . . ?
C1 C2 C3 118.9(3) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C2 C3 C5 120.4(3) . . ?
C2 C3 S1 123.2(3) . . ?
C5 C3 S1 116.4(2) . . ?
O1 C4 S1 122.9(3) . . ?
O1 C4 S2 122.8(3) . . ?
S1 C4 S2 114.35(19) . . ?
C6 C5 C3 119.5(3) . . ?
C6 C5 S2 122.9(2) . . ?
C3 C5 S2 117.6(3) . . ?
C7 C6 C5 120.0(3) . . ?
C7 C6 C8 121.2(3) . . ?
C5 C6 C8 118.8(3) . . ?
C6 C7 C1 119.4(3) . . ?
C6 C7 H3 120.3 . . ?
C1 C7 H3 120.3 . . ?
N1 C8 C6 178.8(4) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.67
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         1.051
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.092
