#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:14:54 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179564 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/33/4503323.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4503323
loop_
_publ_author_name
'Alberola, Antonio'
'Clements, Owen P.'
'Collis, Rebecca J.'
'Cubbitt, Louisa'
'Grant, Craig M.'
'Less, Robert J.'
'Oakley, Richard T.'
'Rawson, Jeremy M.'
'Reed, Robert W.'
'Robertson, Craig M.'
_publ_section_title
;
 Polymorphism in a π-Stacked 1,3,2-Dithiazolyl Radical:
 Pyridyl-1,3,2-Dithiazolyl
;
_journal_issue                   1
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              155
_journal_paper_doi               10.1021/cg7010056
_journal_volume                  8
_journal_year                    2008
_chemical_formula_sum            'C5 H3 N2 S2'
_chemical_formula_weight         155.21
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.217(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.1262(3)
_cell_length_b                   14.4772(6)
_cell_length_c                   7.2157(3)
_cell_measurement_reflns_used    2766
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      54.306
_cell_measurement_theta_min      6.044
_cell_volume                     596.58(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1556
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.81
_exptl_absorpt_coefficient_mu    0.779
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.724
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.728
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1556
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.989
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0378
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0583P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0872
_refine_ls_wR_factor_ref         0.0889
_reflns_number_gt                1256
_reflns_number_total             1349
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg7010056-file003.cif
_cod_data_source_block           pydtam
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               4503323
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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
S3 S 0.02103(16) 0.47209(6) 0.17714(16) 0.0467(3) Uani 1 1 d .
S1 S 0.07636(17) 0.47227(7) 0.65964(18) 0.0530(3) Uani 1 1 d .
S2 S 0.53540(17) 0.52023(7) 0.72357(17) 0.0542(3) Uani 1 1 d .
S4 S 0.48660(18) 0.51131(6) 0.25033(19) 0.0590(3) Uani 1 1 d .
C2 C 0.3535(7) 0.6152(3) 0.6888(6) 0.0393(9) Uani 1 1 d .
C1 C 0.1203(6) 0.5916(3) 0.6573(6) 0.0383(8) Uani 1 1 d .
N2 N -0.0537(6) 0.6522(2) 0.6241(5) 0.0461(8) Uani 1 1 d .
C7 C 0.3126(7) 0.6089(3) 0.1971(6) 0.0402(9) Uani 1 1 d .
N4 N -0.0907(5) 0.6533(2) 0.1223(5) 0.0453(8) Uani 1 1 d .
C6 C 0.0780(6) 0.5902(3) 0.1630(5) 0.0363(8) Uani 1 1 d .
N1 N 0.3457(6) 0.4373(2) 0.7076(6) 0.0583(10) Uani 1 1 d .
N3 N 0.2863(6) 0.4314(2) 0.2258(6) 0.0569(10) Uani 1 1 d .
C8 C 0.3769(7) 0.7006(3) 0.1890(6) 0.0504(10) Uani 1 1 d .
H8 H 0.5314 0.7166 0.2116 0.061 Uiso 1 1 calc R
C3 C 0.4075(7) 0.7076(3) 0.6848(6) 0.0467(10) Uani 1 1 d .
H3 H 0.5596 0.7265 0.7057 0.056 Uiso 1 1 calc R
C9 C 0.2048(7) 0.7668(3) 0.1465(7) 0.0519(10) Uani 1 1 d .
H9 H 0.2413 0.8287 0.1387 0.062 Uiso 1 1 calc R
C10 C -0.0224(7) 0.7409(3) 0.1156(6) 0.0490(10) Uani 1 1 d .
H10 H -0.1353 0.7871 0.0883 0.059 Uiso 1 1 calc R
C5 C 0.0041(7) 0.7410(3) 0.6203(6) 0.0484(10) Uani 1 1 d .
H5 H -0.1129 0.7852 0.5971 0.058 Uiso 1 1 calc R
C4 C 0.2291(7) 0.7707(3) 0.6491(7) 0.0495(10) Uani 1 1 d .
H4 H 0.2594 0.8334 0.6443 0.059 Uiso 1 1 calc R
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N3 S3 C6 99.16(19)
N1 S1 C1 99.24(19)
N1 S2 C2 99.66(17)
N3 S4 C7 100.05(18)
C3 C2 C1 118.0(4)
C3 C2 S2 128.8(3)
C1 C2 S2 113.3(3)
N2 C1 C2 124.7(3)
N2 C1 S1 122.4(3)
C2 C1 S1 112.9(3)
C1 N2 C5 115.8(3)
C8 C7 C6 117.9(4)
C8 C7 S4 128.9(3)
C6 C7 S4 113.2(3)
C6 N4 C10 115.5(3)
N4 C6 C7 125.0(4)
N4 C6 S3 121.8(3)
C7 C6 S3 113.2(3)
S1 N1 S2 114.9(2)
S3 N3 S4 114.3(2)
C9 C8 C7 117.9(4)
C9 C8 H8 121.0
C7 C8 H8 121.0
C4 C3 C2 117.9(4)
C4 C3 H3 121.1
C2 C3 H3 121.1
C8 C9 C10 119.6(4)
C8 C9 H9 120.2
C10 C9 H9 120.2
N4 C10 C9 124.1(4)
N4 C10 H10 118.0
C9 C10 H10 118.0
N2 C5 C4 123.5(4)
N2 C5 H5 118.2
C4 C5 H5 118.2
C3 C4 C5 120.1(4)
C3 C4 H4 120.0
C5 C4 H4 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S3 N3 1.643(4)
S3 C6 1.755(4)
S1 N1 1.639(4)
S1 C1 1.750(4)
S2 N1 1.646(4)
S2 C2 1.730(4)
S4 N3 1.648(4)
S4 C7 1.727(4)
C2 C3 1.381(6)
C2 C1 1.405(5)
C1 N2 1.333(5)
N2 C5 1.336(5)
C7 C8 1.393(6)
C7 C6 1.394(5)
N4 C6 1.331(5)
N4 C10 1.342(5)
C8 C9 1.375(6)
C8 H8 0.9300
C3 C4 1.376(6)
C3 H3 0.9300
C9 C10 1.379(6)
C9 H9 0.9300
C10 H10 0.9300
C5 C4 1.386(6)
C5 H5 0.9300
C4 H4 0.9300
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
N1 S2 C2 C3 -179.7(4)
N1 S2 C2 C1 -1.0(3)
C3 C2 C1 N2 -0.1(6)
S2 C2 C1 N2 -179.0(3)
C3 C2 C1 S1 178.4(3)
S2 C2 C1 S1 -0.5(4)
N1 S1 C1 N2 -179.7(4)
N1 S1 C1 C2 1.8(4)
C2 C1 N2 C5 0.4(6)
S1 C1 N2 C5 -177.9(3)
N3 S4 C7 C8 -178.7(4)
N3 S4 C7 C6 2.8(3)
C10 N4 C6 C7 -0.2(6)
C10 N4 C6 S3 -179.8(3)
C8 C7 C6 N4 0.2(6)
S4 C7 C6 N4 178.9(3)
C8 C7 C6 S3 179.9(3)
S4 C7 C6 S3 -1.5(4)
N3 S3 C6 N4 179.1(3)
N3 S3 C6 C7 -0.6(4)
C1 S1 N1 S2 -2.5(3)
C2 S2 N1 S1 2.2(3)
C6 S3 N3 S4 2.5(3)
C7 S4 N3 S3 -3.2(3)
C6 C7 C8 C9 -0.4(6)
S4 C7 C8 C9 -178.8(3)
C1 C2 C3 C4 -0.4(6)
S2 C2 C3 C4 178.3(3)
C7 C8 C9 C10 0.6(7)
C6 N4 C10 C9 0.4(6)
C8 C9 C10 N4 -0.6(7)
C1 N2 C5 C4 -0.2(6)
C2 C3 C4 C5 0.6(7)
N2 C5 C4 C3 -0.3(7)
