# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# 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_sebdt_rep
_database_code_depnum_ccdc_archive 'CCDC 1412747'
_audit_update_record             
;
2015-07-14 deposited with the CCDC.
2017-08-31 downloaded from the CCDC.
;
_audit_creation_date             2014-08-11
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        SebdtSe
_chemical_formula_moiety         'C22 H22 N4 S Se2'
_chemical_formula_sum            'C22 H22 N4 S Se2'
_chemical_formula_weight         532.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         C22N4H22S1Se2
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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   24.2226(12)
_cell_length_b                   7.8812(3)
_cell_length_c                   25.4161(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 120.284(7)
_cell_angle_gamma                90.00
_cell_volume                     4189.9(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4324
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      27.8080
_cell_measurement_theta_min      2.7570
_exptl_absorpt_coefficient_mu    3.647
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63590
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.694
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2128.0
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.09
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8297
_diffrn_reflns_theta_full        28.15
_diffrn_reflns_theta_max         28.15
_diffrn_reflns_theta_min         1.86
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9983
_diffrn_measured_fraction_theta_max 0.9983
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   17.00   98.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       27.3512   38.0000  -90.0000 81

#__ type_ start__ end____ width___ exp.time_
  2 omega   75.00  119.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       27.3512  178.0000  -30.0000 44

#__ type_ start__ end____ width___ exp.time_
  3 omega   77.00  116.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       27.3512  178.0000   60.0000 39

#__ type_ start__ end____ width___ exp.time_
  4 omega  -36.00   69.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       27.3512  -38.0000   90.0000 105
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0195643000
_diffrn_orient_matrix_UB_12      -0.0128054000
_diffrn_orient_matrix_UB_13      -0.0130504000
_diffrn_orient_matrix_UB_21      0.0269901000
_diffrn_orient_matrix_UB_22      -0.0110672000
_diffrn_orient_matrix_UB_23      0.0295173000
_diffrn_orient_matrix_UB_31      -0.0062134000
_diffrn_orient_matrix_UB_32      -0.0883713000
_diffrn_orient_matrix_UB_33      -0.0018253000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                4083
_reflns_number_total             4540
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         1.325
_refine_diff_density_min         -0.923
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4540
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0347
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0484P)²+5.3396P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0856
_refine_ls_wR_factor_ref         0.0892
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
H10 H 0.7928 0.5842 0.5286 0.026 Uiso 1 1 calc R . .
H11 H 0.8517 0.6334 0.6357 0.023 Uiso 1 1 calc R . .
H17 H 0.6482 0.6785 0.9222 0.027 Uiso 1 1 calc R . .
H19 H 0.7463 0.6486 0.9233 0.022 Uiso 1 1 calc R . .
H22a H 0.8156 0.5120 0.8152 0.018 Uiso 1 1 calc R . .
H22b H 0.7946 0.4578 0.8618 0.018 Uiso 1 1 calc R . .
H23a H 0.8375 0.7270 0.9127 0.020 Uiso 1 1 calc R . .
H23b H 0.8684 0.7458 0.8716 0.020 Uiso 1 1 calc R . .
H24a H 0.9214 0.4738 0.9149 0.024 Uiso 1 1 calc R . .
H24b H 0.9489 0.6323 0.9578 0.024 Uiso 1 1 calc R . .
H25a H 0.8630 0.4003 0.9630 0.041 Uiso 1 1 calc R . .
H25b H 0.8935 0.5550 1.0072 0.041 Uiso 1 1 calc R . .
H25c H 0.9366 0.4029 1.0100 0.041 Uiso 1 1 calc R . .
H26a H 0.8282 0.7720 0.7758 0.018 Uiso 1 1 calc R . .
H26b H 0.8413 0.8291 0.7241 0.018 Uiso 1 1 calc R . .
H27a H 0.9040 0.5776 0.7424 0.021 Uiso 1 1 calc R . .
H27b H 0.8953 0.5392 0.7984 0.021 Uiso 1 1 calc R . .
H28a H 0.9569 0.8346 0.7893 0.027 Uiso 1 1 calc R . .
H28b H 0.9492 0.7928 0.8456 0.027 Uiso 1 1 calc R . .
H29a H 1.0259 0.6046 0.8122 0.046 Uiso 1 1 calc R . .
H29b H 1.0165 0.5546 0.8668 0.046 Uiso 1 1 calc R . .
H29c H 1.0523 0.7228 0.8694 0.046 Uiso 1 1 calc R . .
C1 C 0.80153(13) 0.5547(3) 0.84231(12) 0.0148(6) Uani 1 1 d . . .
C2 C 0.85438(13) 0.6643(4) 0.89105(13) 0.0170(6) Uani 1 1 d . . .
C3 C 0.91189(13) 0.5588(4) 0.93684(13) 0.0198(6) Uani 1 1 d . . .
C4 C 0.90018(15) 0.4712(4) 0.98358(14) 0.0271(7) Uani 1 1 d . . .
C5 C 0.83595(13) 0.7309(3) 0.74415(13) 0.0150(6) Uani 1 1 d . . .
C6 C 0.89797(13) 0.6293(4) 0.77380(13) 0.0176(6) Uani 1 1 d . . .
C7 C 0.95517(14) 0.7429(4) 0.81387(14) 0.0229(6) Uani 1 1 d . . .
C8 C 1.01827(15) 0.6474(5) 0.84327(15) 0.0309(8) Uani 1 1 d . . .
C9 C 0.76845(13) 0.6083(3) 0.64073(13) 0.0160(6) Uani 1 1 d . . .
C10 C 0.80785(14) 0.6134(4) 0.61387(13) 0.0193(6) Uani 1 1 d . . .
C11 C 0.77414(14) 0.5858(4) 0.55286(14) 0.0216(6) Uani 1 1 d . . .
C12 C 0.70385(13) 0.5814(3) 0.60179(12) 0.0148(5) Uani 1 1 d . . .
C13 C 0.67243(12) 0.5963(3) 0.63555(12) 0.0125(5) Uani 1 1 d . . .
C14 C 0.60668(13) 0.6037(3) 0.61875(12) 0.0132(5) Uani 1 1 d . . .
C15 C 0.58950(13) 0.6520(3) 0.66299(12) 0.0136(5) Uani 1 1 d . . .
C16 C 0.63871(12) 0.6708(3) 0.72564(12) 0.0121(5) Uani 1 1 d . . .
C17 C 0.63717(13) 0.6850(3) 0.78029(12) 0.0138(5) Uani 1 1 d . . .
C18 C 0.65108(15) 0.6780(4) 0.88707(13) 0.0222(6) Uani 1 1 d . . .
C19 C 0.70700(14) 0.6615(4) 0.88785(13) 0.0184(6) Uani 1 1 d . . .
C20 C 0.69927(13) 0.6662(3) 0.82836(12) 0.0143(5) Uani 1 1 d . . .
C21 C 0.70353(13) 0.6478(3) 0.74266(12) 0.0132(5) Uani 1 1 d . . .
C22 C 0.72062(12) 0.6274(3) 0.69635(12) 0.0127(5) Uani 1 1 d . . .
N1 N 0.74040(10) 0.6447(3) 0.80585(10) 0.0127(5) Uani 1 1 d . . .
N2 N 0.77938(11) 0.6350(3) 0.69924(10) 0.0138(5) Uani 1 1 d . . .
N3 N 0.55666(11) 0.5749(3) 0.56348(10) 0.0160(5) Uani 1 1 d . . .
N4 N 0.52649(11) 0.6631(3) 0.64007(10) 0.0158(5) Uani 1 1 d . . .
S1 S 0.49280(3) 0.61016(9) 0.56821(3) 0.01769(16) Uani 1 1 d . . .
Se1 Se 0.579441(13) 0.69964(4) 0.808297(12) 0.01741(9) Uani 1 1 d . . .
Se2 Se 0.686078(14) 0.55101(4) 0.521780(12) 0.01807(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
C1 C2 1.523(4) . ?
C3 C2 1.533(4) . ?
C3 C4 1.519(4) . ?
C5 C6 1.525(4) . ?
C6 C7 1.528(4) . ?
C7 C8 1.519(4) . ?
C10 C9 1.427(4) . ?
C10 C11 1.357(4) . ?
C12 C9 1.382(4) . ?
C12 C13 1.410(4) . ?
C13 C14 1.427(4) . ?
C13 C22 1.411(4) . ?
C15 C14 1.433(4) . ?
C15 C16 1.437(4) . ?
C17 C16 1.412(4) . ?
C17 C20 1.387(4) . ?
C18 C19 1.351(4) . ?
C19 C20 1.427(4) . ?
C21 C16 1.414(4) . ?
C21 C22 1.440(4) . ?
N1 C1 1.473(3) . ?
N1 C20 1.387(3) . ?
N1 C21 1.390(3) . ?
N2 C5 1.475(3) . ?
N2 C9 1.389(3) . ?
N2 C22 1.389(3) . ?
N3 C14 1.333(3) . ?
N4 C15 1.334(3) . ?
S1 N3 1.635(2) . ?
S1 N4 1.635(2) . ?
Se1 C17 1.865(3) . ?
Se1 C18 1.883(3) . ?
Se2 C11 1.884(3) . ?
Se2 C12 1.869(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 113.9(2) . . ?
C1 C2 C3 112.3(2) . . ?
C4 C3 C2 112.6(3) . . ?
N2 C5 C6 114.4(2) . . ?
C5 C6 C7 110.9(2) . . ?
C8 C7 C6 112.7(3) . . ?
C12 C9 C10 116.8(3) . . ?
C12 C9 N2 109.0(2) . . ?
N2 C9 C10 134.1(3) . . ?
C11 C10 C9 112.3(3) . . ?
C10 C11 Se2 113.8(2) . . ?
C9 C12 C13 108.4(2) . . ?
C9 C12 Se2 110.8(2) . . ?
C13 C12 Se2 140.7(2) . . ?
C12 C13 C14 133.2(2) . . ?
C12 C13 C22 106.2(2) . . ?
C22 C13 C14 120.2(2) . . ?
C13 C14 C15 119.9(2) . . ?
N3 C14 C13 126.3(2) . . ?
N3 C14 C15 113.8(2) . . ?
C14 C15 C16 119.4(2) . . ?
N4 C15 C14 113.3(2) . . ?
N4 C15 C16 127.2(2) . . ?
C17 C16 C15 132.8(3) . . ?
C17 C16 C21 106.6(2) . . ?
C21 C16 C15 119.9(2) . . ?
C16 C17 Se1 141.0(2) . . ?
C20 C17 C16 107.6(2) . . ?
C20 C17 Se1 111.1(2) . . ?
C19 C18 Se1 113.8(2) . . ?
C18 C19 C20 112.8(3) . . ?
C17 C20 C19 116.1(3) . . ?
N1 C20 C17 109.6(2) . . ?
N1 C20 C19 134.1(3) . . ?
C16 C21 C22 119.8(2) . . ?
N1 C21 C16 108.8(2) . . ?
N1 C21 C22 131.3(2) . . ?
C13 C22 C21 119.6(2) . . ?
N2 C22 C13 109.0(2) . . ?
N2 C22 C21 131.4(2) . . ?
C20 N1 C1 120.2(2) . . ?
C20 N1 C21 107.3(2) . . ?
C21 N1 C1 126.3(2) . . ?
C9 N2 C5 120.5(2) . . ?
C9 N2 C22 107.5(2) . . ?
C22 N2 C5 126.2(2) . . ?
C14 N3 S1 106.52(19) . . ?
C15 N4 S1 106.73(19) . . ?
N3 S1 N4 99.66(12) . . ?
C17 Se1 C18 86.21(13) . . ?
C12 Se2 C11 86.23(13) . . ?

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# 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_SSZ_SG_BDSe
_database_code_depnum_ccdc_archive 'CCDC 1412608'
_audit_update_record             
;
2015-07-14 deposited with the CCDC.
2017-08-31 downloaded from the CCDC.
;
_chemical_formula_moiety         'C22 H22 N4 S2 Se'
_chemical_formula_sum            'C22 H22 N4 S2 Se'
_chemical_formula_weight         485.54
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Se -0.08110 2.30834 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z-1/2
5 x+1/2,y+1/2,z
6 -x+1/2,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z
8 x+1/2,-y+1/2,z-1/2

_cell_length_a                   24.0368(11)
_cell_length_b                   7.8856(3)
_cell_length_c                   24.6824(11)
_cell_angle_alpha                90
_cell_angle_beta                 118.162(6)
_cell_angle_gamma                90
_cell_volume                     4124.6(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293.15
_exptl_absorpt_coefficient_mu    2.040
_exptl_absorpt_correction_T_max  0.815
_exptl_absorpt_correction_T_min  0.619
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.5637
_exptl_crystal_description       needle
_exptl_crystal_F_000             1984.0
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            8021
_diffrn_reflns_theta_full        24.999171
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.87
_diffrn_ambient_temperature      293.15
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000000
_diffrn_measured_fraction_theta_max 1.000000
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              25
_reflns_limit_h_min              -28
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              29
_reflns_limit_l_min              0
_reflns_number_gt                3305
_reflns_number_total             3628
_reflns_threshold_expression     I>=2u(I)
_refine_diff_density_max         0.777934
_refine_diff_density_min         -0.478628
_refine_diff_density_rms         0.094758
_refine_ls_d_res_high            0.840891
_refine_ls_d_res_low             10.880239
_refine_ls_goodness_of_fit_ref   0.950288
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    34
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3628
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.035303
_refine_ls_R_factor_gt           0.031109
_refine_ls_restrained_S_all      0.950288
_refine_ls_shift/su_max          0.0009
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.116105
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
Se1 Se 0.171190(12) 0.34021(4) 0.437591(12) 0.01506(14) Uani 1.000000 .
S2 S 0.02499(3) 0.44213(9) 0.19393(3) 0.01487(19) Uani 1.000000 .
S1 S 0.41381(3) 0.28943(9) 0.47571(3) 0.01468(19) Uani 1.000000 .
C20 C 0.37960(13) 0.3471(3) 0.36157(14) 0.0126(6) Uani 1.000000 .
N1 N 0.33110(11) 0.3748(3) 0.30266(11) 0.0115(5) Uani 1.000000 .
N3 N 0.13306(10) 0.4047(3) 0.35795(10) 0.0134(5) Uani 1.000000 .
C9 C 0.11876(13) 0.4083(3) 0.17135(13) 0.0121(6) Uani 1.000000 .
N2 N 0.18350(11) 0.3848(3) 0.19440(10) 0.0111(5) Uani 1.000000 .
C2 C 0.37560(13) 0.3679(3) 0.22839(13) 0.0136(6) Uani 1.000000 .
H9a H 0.41387(13) 0.3181(3) 0.26055(13) 0.0163(7) Uiso 1.000000 R
H9b H 0.34827(13) 0.2764(3) 0.20400(13) 0.0163(7) Uiso 1.000000 R
C17 C 0.35475(13) 0.3163(3) 0.40114(13) 0.0118(6) Uani 1.000000 .
C13 C 0.16265(12) 0.4103(3) 0.27554(12) 0.0095(5) Uani 1.000000 .
C12 C 0.10535(12) 0.4261(3) 0.22019(12) 0.0118(6) Uani 1.000000 .
C22 C 0.21023(13) 0.3868(3) 0.25835(12) 0.0102(5) Uani 1.000000 .
C21 C 0.27483(13) 0.3644(3) 0.30532(13) 0.0105(6) Uani 1.000000 .
C18 C 0.47125(14) 0.3250(3) 0.45247(15) 0.0176(7) Uani 1.000000 .
H15 H 0.51433(14) 0.3240(3) 0.47945(15) 0.0212(8) Uiso 1.000000 R
N4 N 0.24665(10) 0.3010(3) 0.43973(11) 0.0123(5) Uani 1.000000 .
C8 C 0.16468(15) 0.1993(4) 0.01582(14) 0.0220(7) Uani 1.000000 .
H17a H 0.1345(4) 0.2817(4) -0.0102(6) 0.0330(10) Uiso 1.000000 G
H17b H 0.1756(2) 0.126(2) -0.0087(6) 0.0330(10) Uiso 1.000000 G
H17c H 0.1467(6) 0.134(2) 0.03648(14) 0.0330(10) Uiso 1.000000 G
C16 C 0.28819(13) 0.3303(3) 0.36644(13) 0.0108(6) Uani 1.000000 .
C1 C 0.34243(13) 0.4704(3) 0.25735(12) 0.0122(6) Uani 1.000000 .
H19a H 0.30226(13) 0.5102(3) 0.22497(12) 0.0147(7) Uiso 1.000000 R
H19b H 0.36785(13) 0.5693(3) 0.27739(12) 0.0147(7) Uiso 1.000000 R
C6 C 0.21108(14) 0.3981(4) 0.10789(13) 0.0146(6) Uani 1.000000 .
H20a H 0.24453(14) 0.4813(4) 0.12697(13) 0.0176(7) Uiso 1.000000 R
H20b H 0.17161(14) 0.4588(4) 0.08522(13) 0.0176(7) Uiso 1.000000 R
C15 C 0.23874(13) 0.3357(3) 0.38403(13) 0.0113(6) Uani 1.000000 .
C11 C 0.01115(14) 0.4238(4) 0.11832(13) 0.0185(6) Uani 1.000000 .
H22 H -0.02906(14) 0.4265(4) 0.08477(13) 0.0222(8) Uiso 1.000000 R
C10 C 0.06460(13) 0.4053(4) 0.11273(13) 0.0163(6) Uani 1.000000 .
H23 H 0.06543(13) 0.3924(4) 0.07566(13) 0.0196(7) Uiso 1.000000 R
C14 C 0.17537(12) 0.3904(3) 0.33825(13) 0.0108(6) Uani 1.000000 .
C7 C 0.22348(14) 0.2893(4) 0.06302(13) 0.0166(6) Uani 1.000000 .
H25a H 0.25551(14) 0.2055(4) 0.08616(13) 0.0199(7) Uiso 1.000000 R
H25b H 0.23975(14) 0.3613(4) 0.04186(13) 0.0199(7) Uiso 1.000000 R
C5 C 0.20776(13) 0.2909(3) 0.15791(13) 0.0121(6) Uani 1.000000 .
H26a H 0.24964(13) 0.2486(3) 0.18541(13) 0.0145(7) Uiso 1.000000 R
H26b H 0.18072(13) 0.1939(3) 0.13885(13) 0.0145(7) Uiso 1.000000 R
C3 C 0.39209(14) 0.4808(4) 0.18756(14) 0.0200(6) Uani 1.000000 .
H27a H 0.35370(14) 0.5311(4) 0.15578(14) 0.0240(8) Uiso 1.000000 R
H27b H 0.41934(14) 0.5721(4) 0.21218(14) 0.0240(8) Uiso 1.000000 R
C19 C 0.44687(14) 0.3541(3) 0.39125(14) 0.0166(6) Uani 1.000000 .
H28 H 0.47076(14) 0.3757(3) 0.37138(14) 0.0200(8) Uiso 1.000000 R
C4 C 0.42492(15) 0.3834(4) 0.15761(15) 0.0271(8) Uani 1.000000 .
H29a H 0.4308(9) 0.4565(9) 0.1297(8) 0.0406(11) Uiso 1.000000 G
H29b H 0.4652(5) 0.344(2) 0.18873(18) 0.0406(11) Uiso 1.000000 G
H29c H 0.3995(5) 0.2881(16) 0.1355(8) 0.0406(11) Uiso 1.000000 G


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Se1 N3 1.806(2) .
Se1 N4 1.816(2) .
S2 C12 1.728(3) .
S2 C11 1.740(3) .
S1 C17 1.727(3) .
S1 C18 1.750(3) .
C20 N1 1.386(4) .
C20 C17 1.386(4) .
C20 C19 1.427(4) .
N1 C21 1.387(3) .
N1 C1 1.477(3) .
N3 C14 1.323(3) .
C9 N2 1.394(3) .
C9 C12 1.394(4) .
C9 C10 1.418(4) .
N2 C22 1.396(3) .
N2 C5 1.482(3) .
C2 H9a 0.9700 .
C2 H9b 0.9700 .
C2 C1 1.529(4) .
C2 C3 1.531(4) .
C17 C16 1.418(4) .
C13 C12 1.415(4) .
C13 C22 1.407(4) .
C13 C14 1.438(4) .
C22 C21 1.445(4) .
C21 C16 1.412(4) .
C18 H15 0.9300 .
C18 C19 1.358(4) .
N4 C15 1.325(4) .
C8 H17a 0.9600 .
C8 H17b 0.9600 .
C8 H17c 0.9600 .
C8 C7 1.518(4) .
C16 C15 1.446(4) .
C1 H19a 0.9700 .
C1 H19b 0.9700 .
C6 H20a 0.9700 .
C6 H20b 0.9700 .
C6 C7 1.537(4) .
C6 C5 1.529(4) .
C15 C14 1.469(4) .
C11 H22 0.9300 .
C11 C10 1.363(4) .
C10 H23 0.9300 .
C7 H25a 0.9700 .
C7 H25b 0.9700 .
C5 H26a 0.9700 .
C5 H26b 0.9700 .
C3 H27a 0.9700 .
C3 H27b 0.9700 .
C3 C4 1.520(4) .
C19 H28 0.9300 .
C4 H29a 0.9600 .
C4 H29b 0.9600 .
C4 H29c 0.9600 .

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
N4 Se1 N3 93.80(10) . .
C11 S2 C12 90.59(13) . .
C18 S1 C17 90.57(14) . .
C17 C20 N1 109.8(2) . .
C19 C20 N1 136.1(3) . .
C19 C20 C17 114.0(3) . .
C21 N1 C20 107.3(2) . .
C1 N1 C20 120.7(2) . .
C1 N1 C21 126.8(2) . .
C14 N3 Se1 107.03(18) . .
C12 C9 N2 109.2(2) . .
C10 C9 N2 136.4(3) . .
C10 C9 C12 114.1(2) . .
C22 N2 C9 106.8(2) . .
C5 N2 C9 120.1(2) . .
C5 N2 C22 126.2(2) . .
H9b C2 H9a 108.1 . .
C1 C2 H9a 109.50(15) . .
C1 C2 H9b 109.50(15) . .
C3 C2 H9a 109.50(15) . .
C3 C2 H9b 109.50(16) . .
C3 C2 C1 110.7(2) . .
C20 C17 S1 111.2(2) . .
C16 C17 S1 141.1(2) . .
C16 C17 C20 107.4(3) . .
C22 C13 C12 106.3(2) . .
C14 C13 C12 131.6(2) . .
C14 C13 C22 121.3(2) . .
C9 C12 S2 110.9(2) . .
C13 C12 S2 140.8(2) . .
C13 C12 C9 108.0(2) . .
C13 C22 N2 109.7(2) . .
C21 C22 N2 130.8(2) . .
C21 C22 C13 119.5(2) . .
C22 C21 N1 131.1(3) . .
C16 C21 N1 109.1(2) . .
C16 C21 C22 119.8(2) . .
H15 C18 S1 123.24(10) . .
C19 C18 S1 113.5(2) . .
C19 C18 H15 123.24(17) . .
C15 N4 Se1 106.41(18) . .
H17b C8 H17a 109.5 . .
H17c C8 H17a 109.5 . .
H17c C8 H17b 109.5 . .
C7 C8 H17a 109.5 . .
C7 C8 H17b 109.5 . .
C7 C8 H17c 109.5 . .
C21 C16 C17 106.4(2) . .
C15 C16 C17 132.4(3) . .
C15 C16 C21 120.7(2) . .
C2 C1 N1 114.0(2) . .
H19a C1 N1 108.75(14) . .
H19a C1 C2 108.75(15) . .
H19b C1 N1 108.75(14) . .
H19b C1 C2 108.75(14) . .
H19b C1 H19a 107.6 . .
H20b C6 H20a 107.9 . .
C7 C6 H20a 109.21(15) . .
C7 C6 H20b 109.21(16) . .
C5 C6 H20a 109.21(15) . .
C5 C6 H20b 109.21(15) . .
C5 C6 C7 112.0(2) . .
C16 C15 N4 124.7(3) . .
C14 C15 N4 116.6(2) . .
C14 C15 C16 118.6(2) . .
H22 C11 S2 123.05(10) . .
C10 C11 S2 113.9(2) . .
C10 C11 H22 123.05(17) . .
C11 C10 C9 110.5(3) . .
H23 C10 C9 124.76(16) . .
H23 C10 C11 124.76(17) . .
C13 C14 N3 125.2(2) . .
C15 C14 N3 116.1(2) . .
C15 C14 C13 118.5(2) . .
C6 C7 C8 112.8(2) . .
H25a C7 C8 109.04(17) . .
H25a C7 C6 109.04(16) . .
H25b C7 C8 109.04(16) . .
H25b C7 C6 109.04(15) . .
H25b C7 H25a 107.8 . .
C6 C5 N2 113.6(2) . .
H26a C5 N2 108.85(14) . .
H26a C5 C6 108.85(15) . .
H26b C5 N2 108.85(14) . .
H26b C5 C6 108.85(15) . .
H26b C5 H26a 107.7 . .
H27a C3 C2 109.11(15) . .
H27b C3 C2 109.11(16) . .
H27b C3 H27a 107.8 . .
C4 C3 C2 112.4(2) . .
C4 C3 H27a 109.11(17) . .
C4 C3 H27b 109.11(18) . .
C18 C19 C20 110.7(3) . .
H28 C19 C20 124.63(17) . .
H28 C19 C18 124.63(17) . .
H29a C4 C3 109.5 . .
H29b C4 C3 109.5 . .
H29b C4 H29a 109.5 . .
H29c C4 C3 109.5 . .
H29c C4 H29a 109.5 . .
H29c C4 H29b 109.5 . .

_chemical_name_systematic        SbdSeS
####################################################################### 
# 
# 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_ssz_sg_butyl
_database_code_depnum_ccdc_archive 'CCDC 1412607'
_audit_update_record             
;
2015-07-14 deposited with the CCDC.
2017-08-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        SbdtS
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H22 N4 S3'
_chemical_formula_sum            'C22 H22 N4 S3'
_chemical_formula_weight         438.62

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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/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                   20.6742(8)
_cell_length_b                   14.3417(5)
_cell_length_c                   16.3414(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.545(4)
_cell_angle_gamma                90.00
_cell_volume                     4506.7(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1840
_exptl_absorpt_coefficient_mu    3.123
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.496
_exptl_absorpt_correction_T_max  0.755
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3945
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0251
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.28
_diffrn_reflns_theta_max         66.39
_reflns_number_total             3945
_reflns_number_gt                3464
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?


_refine_special_details          SQUEEZE

_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)+(0.0814P)²+0.8943P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3945
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.1245
_refine_ls_wR_factor_gt          0.1189
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_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 0.15426(3) 0.88714(4) 0.28630(3) 0.04911(17) Uani 1 1 d . . .
S2 S -0.11816(2) 0.44575(4) -0.00829(3) 0.04560(17) Uani 1 1 d . . .
S3 S -0.08878(3) 0.80991(4) 0.03511(4) 0.05357(18) Uani 1 1 d . . .
N3 N -0.09528(8) 0.69662(13) 0.03509(11) 0.0446(4) Uani 1 1 d . . .
N1 N 0.15944(7) 0.62177(12) 0.29823(10) 0.0380(4) Uani 1 1 d . . .
N2 N 0.05944(8) 0.45279(11) 0.17721(10) 0.0384(3) Uani 1 1 d . . .
C1 C 0.19052(10) 0.54968(15) 0.36393(12) 0.0417(4) Uani 1 1 d . . .
H1A H 0.1612 0.4946 0.3486 0.050 Uiso 1 1 calc R . .
H1B H 0.1917 0.5716 0.4206 0.050 Uiso 1 1 calc R . .
C20 C 0.17966(9) 0.71351(15) 0.31823(12) 0.0395(4) Uani 1 1 d . . .
N4 N -0.01168(9) 0.82415(12) 0.11042(12) 0.0471(4) Uani 1 1 d . . .
C15 C 0.01166(9) 0.73946(13) 0.13809(12) 0.0362(4) Uani 1 1 d . . .
C14 C -0.03578(9) 0.66579(13) 0.09518(11) 0.0356(4) Uani 1 1 d . . .
C5 C 0.12408(10) 0.39820(14) 0.20451(13) 0.0418(4) Uani 1 1 d . . .
H5A H 0.1632 0.4403 0.2290 0.050 Uiso 1 1 calc R . .
H5B H 0.1280 0.3691 0.1529 0.050 Uiso 1 1 calc R . .
C19 C 0.23516(10) 0.75996(16) 0.38440(13) 0.0470(5) Uani 1 1 d . . .
H19 H 0.2713 0.7304 0.4286 0.056 Uiso 1 1 calc R . .
C21 C 0.09562(9) 0.62284(13) 0.22788(11) 0.0347(4) Uani 1 1 d . . .
C22 C 0.05057(9) 0.54875(13) 0.17817(11) 0.0344(4) Uani 1 1 d . . .
C17 C 0.13109(9) 0.77252(14) 0.26135(12) 0.0388(4) Uani 1 1 d . . .
C18 C 0.22787(11) 0.85330(18) 0.37385(14) 0.0521(5) Uani 1 1 d . . .
H18 H 0.2595 0.8956 0.4103 0.063 Uiso 1 1 calc R . .
C16 C 0.07697(9) 0.71619(14) 0.20488(11) 0.0368(4) Uani 1 1 d . . .
C13 C -0.01532(9) 0.57175(13) 0.11523(12) 0.0353(4) Uani 1 1 d . . .
C6 C 0.12866(11) 0.32280(16) 0.27202(14) 0.0501(5) Uani 1 1 d . . .
H6A H 0.1333 0.3517 0.3276 0.060 Uiso 1 1 calc R . .
H6B H 0.0861 0.2865 0.2522 0.060 Uiso 1 1 calc R . .
C12 C -0.04581(9) 0.48671(14) 0.07669(11) 0.0376(4) Uani 1 1 d . . .
C11 C -0.08491(12) 0.33354(16) 0.00955(14) 0.0507(5) Uani 1 1 d . . .
H11 H -0.1080 0.2824 -0.0233 0.061 Uiso 1 1 calc R . .
C3 C 0.29842(13) 0.4605(2) 0.45230(16) 0.0634(6) Uani 1 1 d . . .
H3A H 0.3016 0.4944 0.5050 0.076 Uiso 1 1 calc R . .
H3B H 0.2695 0.4061 0.4480 0.076 Uiso 1 1 calc R . .
C7 C 0.19012(15) 0.25880(19) 0.2856(2) 0.0702(7) Uani 1 1 d . . .
H7A H 0.1830 0.2261 0.2310 0.084 Uiso 1 1 calc R . .
H7B H 0.2318 0.2964 0.2994 0.084 Uiso 1 1 calc R . .
C9 C -0.00025(10) 0.41677(14) 0.11392(13) 0.0410(4) Uani 1 1 d . . .
C10 C -0.02206(12) 0.32730(15) 0.07599(14) 0.0485(5) Uani 1 1 d . . .
H10 H 0.0032 0.2725 0.0942 0.058 Uiso 1 1 calc R . .
C2 C 0.26401(10) 0.52260(16) 0.37226(13) 0.0486(5) Uani 1 1 d . . .
H2A H 0.2916 0.5785 0.3776 0.058 Uiso 1 1 calc R . .
H2B H 0.2622 0.4898 0.3195 0.058 Uiso 1 1 calc R . .
C4 C 0.37044(16) 0.4290(2) 0.4606(2) 0.0822(9) Uani 1 1 d . . .
H4A H 0.3668 0.3853 0.4147 0.123 Uiso 1 1 calc R . .
H4B H 0.3930 0.3998 0.5168 0.123 Uiso 1 1 calc R . .
H4C H 0.3971 0.4821 0.4557 0.123 Uiso 1 1 calc R . .
C8 C 0.2014(2) 0.1880(3) 0.3579(3) 0.1019(12) Uani 1 1 d . . .
H8A H 0.1590 0.1545 0.3479 0.153 Uiso 1 1 calc R . .
H8B H 0.2153 0.2193 0.4136 0.153 Uiso 1 1 calc R . .
H8C H 0.2371 0.1450 0.3582 0.153 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 C17 1.719(2) . ?
S1 C18 1.732(2) . ?
S2 C12 1.7279(18) . ?
S2 C11 1.732(2) . ?
S3 N4 1.6299(17) . ?
S3 N3 1.6304(19) . ?
N3 C14 1.336(2) . ?
N1 C20 1.383(3) . ?
N1 C21 1.396(2) . ?
N1 C1 1.459(2) . ?
N2 C9 1.386(3) . ?
N2 C22 1.389(2) . ?
N2 C5 1.470(2) . ?
C1 C2 1.525(3) . ?
C20 C17 1.380(3) . ?
C20 C19 1.421(3) . ?
N4 C15 1.324(3) . ?
C15 C16 1.429(2) . ?
C15 C14 1.437(3) . ?
C14 C13 1.416(3) . ?
C5 C6 1.523(3) . ?
C19 C18 1.351(3) . ?
C21 C16 1.406(3) . ?
C21 C22 1.449(3) . ?
C22 C13 1.412(3) . ?
C17 C16 1.413(3) . ?
C13 C12 1.411(3) . ?
C6 C7 1.516(3) . ?
C12 C9 1.358(3) . ?
C11 C10 1.356(3) . ?
C3 C4 1.513(4) . ?
C3 C2 1.526(3) . ?
C7 C8 1.511(4) . ?
C9 C10 1.424(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 S1 C18 90.67(10) . . ?
C12 S2 C11 90.44(10) . . ?
N4 S3 N3 100.53(9) . . ?
C14 N3 S3 106.02(13) . . ?
C20 N1 C21 107.24(16) . . ?
C20 N1 C1 119.16(15) . . ?
C21 N1 C1 129.91(17) . . ?
C9 N2 C22 107.02(15) . . ?
C9 N2 C5 119.27(16) . . ?
C22 N2 C5 129.30(16) . . ?
N1 C1 C2 113.66(16) . . ?
C17 C20 N1 110.03(16) . . ?
C17 C20 C19 114.19(19) . . ?
N1 C20 C19 135.68(18) . . ?
C15 N4 S3 106.01(14) . . ?
N4 C15 C16 126.77(17) . . ?
N4 C15 C14 114.21(16) . . ?
C16 C15 C14 119.01(17) . . ?
N3 C14 C13 126.98(17) . . ?
N3 C14 C15 113.23(17) . . ?
C13 C14 C15 119.69(16) . . ?
N2 C5 C6 113.95(16) . . ?
C18 C19 C20 110.26(19) . . ?
N1 C21 C16 108.31(16) . . ?
N1 C21 C22 132.22(17) . . ?
C16 C21 C22 119.45(15) . . ?
N2 C22 C13 108.62(16) . . ?
N2 C22 C21 132.24(17) . . ?
C13 C22 C21 119.12(16) . . ?
C20 C17 C16 107.16(18) . . ?
C20 C17 S1 110.88(14) . . ?
C16 C17 S1 141.85(15) . . ?
C19 C18 S1 113.96(16) . . ?
C21 C16 C17 107.23(15) . . ?
C21 C16 C15 121.06(16) . . ?
C17 C16 C15 131.63(18) . . ?
C12 C13 C22 106.06(17) . . ?
C12 C13 C14 132.37(17) . . ?
C22 C13 C14 121.17(17) . . ?
C7 C6 C5 111.18(19) . . ?
C9 C12 C13 108.43(16) . . ?
C9 C12 S2 111.24(15) . . ?
C13 C12 S2 139.98(15) . . ?
C10 C11 S2 113.61(16) . . ?
C4 C3 C2 112.6(2) . . ?
C8 C7 C6 113.7(3) . . ?
C12 C9 N2 109.87(17) . . ?
C12 C9 C10 114.46(18) . . ?
N2 C9 C10 135.50(19) . . ?
C11 C10 C9 110.25(19) . . ?
C1 C2 C3 111.16(18) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        66.39
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.054
