#------------------------------------------------------------------------------
#$Date: 2016-02-19 23:18:51 +0100 (vie 19 de feb de 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/94/2019437.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2019437
loop_
_publ_author_name
'Jones, Ray'
_publ_section_title
;
 Three trithiadiazepines and a trithiatriazepine
;
_journal_coeditor_code           QS3029
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              60
_journal_page_last               66
_journal_paper_doi               10.1107/S2053229613033287
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C4 N4 S3'
_chemical_formula_moiety         'C4 N4 S3'
_chemical_formula_sum            'C4 N4 S3'
_chemical_formula_weight         200.26
_chemical_melting_point          413
_chemical_name_common
;
6,7-dicyano-1,3,5,2,4-trithiadiazepine
;
_chemical_name_systematic
;
1,3,5,2,4-Trithiadiazepine-6,7-dicarbonitrile
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.8970(10)
_cell_length_b                   16.881(9)
_cell_length_c                   10.910(4)
_cell_measurement_reflns_used    9
_cell_measurement_temperature    293(2)
_cell_volume                     717.7(5)
_computing_cell_refinement       'Nicolet R3m software'
_computing_data_collection       'Nicolet R3m software'
_computing_data_reduction        'Nicolet R3m software'
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009) and
Mercury (Macrae et al., 2008)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al.,
2009) and
Mercury (Macrae et al., 2008)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS83 (Sheldrick, 1983)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Nicolet R3m'
_diffrn_measurement_method       'scintillation counter'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0624
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            489
_diffrn_reflns_theta_full        56.88
_diffrn_reflns_theta_max         56.88
_diffrn_reflns_theta_min         5.24
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 50
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    8.896
_exptl_absorpt_correction_T_max  0.7400
_exptl_absorpt_correction_T_min  0.5600
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   '(SHELXS83; Sheldrick, 1983)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.853
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.304
_refine_ls_extinction_coef       0.0002(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_matrix_type           full
_refine_ls_number_parameters     52
_refine_ls_number_reflns         489
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.958
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0424
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0464P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0937
_reflns_number_gt                338
_reflns_number_total             489
_reflns_threshold_expression     I>2sigma(I)
_iucr_refine_instructions_details
;
TITL (3) 6,7-Dicyano-1,3,5,2,4-trithiadiazepine $orthorhombic $Pbcn $? $Orange $
CELL  1.54178    3.8970   16.8810   10.9100    90.000    90.000    90.000
ZERR        4    0.0010    0.0090    0.0040     0.000     0.000     0.000
LATT   1
SYMM     0.50000 - X ,    0.50000 - Y ,    0.50000 + Z
SYMM     0.50000 + X ,    0.50000 - Y ,            - Z
SYMM             - X ,              Y ,    0.50000 - Z
SFAC  C  N  S
UNIT    16   16  12
LIST 4
MORE 3
CONF
HTAB
BOND $H
SIZE 0.16 0.04 0.06
TEMP 20
L.S. 10
PLAN 20
FMAP
ACTA
DEFS 0.002 0.2 0.01 0.05
WPDB
WGHT    0.046400
EXTI    0.000210
FVAR       1.30161
S1    3    0.267445    0.341643    0.903113    11.00000    0.05600    0.03189 =
         0.03288    0.00164    0.00686    0.00098
N2    2    0.338764    0.253239    0.858637    11.00000    0.06373    0.02831 =
         0.04055    0.00149    0.00734   -0.00068
S3    3    0.500000    0.207071    0.750000    10.50000    0.07036    0.02700 =
         0.04694    0.00000    0.00760    0.00000
C7    1    0.414072    0.413767    0.805104    11.00000    0.04472    0.02952 =
         0.02779   -0.00172   -0.00917   -0.00026
C8    1    0.319593    0.489471    0.855545    11.00000    0.04915    0.03252 =
         0.02859    0.00167   -0.00368    0.00145
N9    2    0.236993    0.548277    0.895970    11.00000    0.07935    0.04184 =
         0.04591   -0.00194   -0.00644    0.01954
HKLF 3 1  1  0  0  0  0  1  0 -1  0
REM  (3) 6,7-Dicyano-1,3,5,2,4-trithiadiazepine $orthorhombic $Pbcn $? $Orange $
REM R1 =  0.0424 for    338 Fo > 4sig(Fo)  and  0.0678 for all    489 data
REM     52 parameters refined using      0 restraints
END
WGHT      0.0464      0.0000
REM Highest difference peak  0.283,  deepest hole -0.304,  1-sigma level  0.069
Q1    1   0.0458  0.2044  0.7207  11.00000  0.05    0.28
Q2    1   0.0481  0.3791  0.7980  11.00000  0.05    0.23
Q3    1   0.5000  0.6131  0.7500  10.50000  0.05    0.21
Q4    1   0.4482  0.2744  0.7367  11.00000  0.05    0.21
Q5    1   0.3154  0.3791  0.8474  11.00000  0.05    0.20
Q6    1   0.0675  0.3381  0.9383  11.00000  0.05    0.20
Q7    1   0.3094  0.2923  0.8911  11.00000  0.05    0.20
Q8    1   0.2357  0.5544  1.0088  11.00000  0.05    0.19
Q9    1  -0.1669  0.3454  0.8366  11.00000  0.05    0.18
Q10   1   0.0084  0.5639  1.0258  11.00000  0.05    0.18
Q11   1   0.4688  0.4386  0.8596  11.00000  0.05    0.18
Q12   1   0.1791  0.2770  1.0201  11.00000  0.05    0.17
Q13   1   0.5000  0.5000  1.0000  10.50000  0.05    0.17
Q14   1  -0.0194  0.3775  0.9420  11.00000  0.05    0.17
Q15   1   0.5796  0.2492  0.9341  11.00000  0.05    0.17
Q16   1   0.8273  0.2486  0.8860  11.00000  0.05    0.17
Q17   1   0.0132  0.4502  0.8599  11.00000  0.05    0.17
Q18   1   0.5653  0.4066  0.7704  11.00000  0.05    0.16
Q19   1   0.2633  0.4306  0.7819  11.00000  0.05    0.16
Q20   1   0.0000  0.3048  0.7500  10.50000  0.05    0.15
;
_cod_data_source_file            qs3029sup1.cif
_cod_data_source_block           III
_cod_database_code               2019437
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
S S1 0.2674(4) 0.34164(7) 0.90311(10) 0.0403(5) Uani d . 1 1
N N2 0.3388(12) 0.2532(2) 0.8586(4) 0.0442(14) Uani d . 1 1
S S3 0.5000 0.20707(10) 0.7500 0.0481(7) Uani d S 1 2
C C7 0.4141(14) 0.4138(3) 0.8051(4) 0.0340(13) Uani d . 1 1
C C8 0.3196(14) 0.4895(3) 0.8555(4) 0.0368(14) Uani d . 1 1
N N9 0.2370(15) 0.5483(3) 0.8960(4) 0.0557(13) Uani d . 1 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.0560(9) 0.0319(7) 0.0329(7) 0.0010(8) 0.0069(8) 0.0016(6)
N2 0.064(4) 0.028(2) 0.041(2) -0.001(2) 0.007(3) 0.0015(19)
S3 0.0704(16) 0.0270(9) 0.0469(11) 0.000 0.0076(13) 0.000
C7 0.045(3) 0.030(2) 0.028(2) 0.000(3) -0.009(3) -0.002(2)
C8 0.049(4) 0.033(3) 0.029(3) 0.001(3) -0.004(3) 0.002(2)
N9 0.079(4) 0.042(3) 0.046(3) 0.020(3) -0.006(3) -0.002(2)
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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
N2 S1 C7 . . 114.6(2)
S3 N2 S1 . . 140.7(3)
N2 S3 N2 . 4_656 119.7(3)
C7 C7 C8 4_656 . 117.3(3)
C7 C7 S1 4_656 . 134.87(16)
C8 C7 S1 . . 107.8(3)
N9 C8 C7 . . 178.2(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
S1 N2 . 1.594(4)
S1 C7 . 1.718(5)
N2 S3 . 1.551(4)
S3 N2 4_656 1.551(4)
C7 C7 4_656 1.376(9)
C7 C8 . 1.439(7)
C8 N9 . 1.133(6)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_4
_geom_torsion
C7 S1 N2 S3 . -1.2(6)
S1 N2 S3 N2 4_656 1.0(4)
N2 S1 C7 C7 4_656 -0.8(9)
N2 S1 C7 C8 . 177.9(3)
