#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:14:54 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179564 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/33/4503324.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_4503324
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           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 100.052(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   6.062(4)
_cell_length_b                   14.537(9)
_cell_length_c                   13.716(9)
_cell_measurement_reflns_used    3046
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      54.529
_cell_measurement_theta_min      5.605
_cell_volume                     1190.1(13)
_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      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0790
_diffrn_reflns_av_sigmaI/netI    0.0777
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9500
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         3.33
_exptl_absorpt_coefficient_mu    0.781
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.732
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.327
_exptl_crystal_size_mid          0.139
_exptl_crystal_size_min          0.024
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2464
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0949
_refine_ls_R_factor_gt           0.0637
_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)+(0.0624P)²+1.0573P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1434
_refine_ls_wR_factor_ref         0.1565
_reflns_number_gt                1774
_reflns_number_total             2464
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg7010056-file004.cif
_cod_data_source_block           rto17rt
_cod_original_cell_volume        1190.2(13)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4503324
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 1.02811(17) 0.59423(7) 0.57959(8) 0.0330(3) Uani 1 1 d .
S1 S 0.77173(17) 0.91184(7) 0.31046(8) 0.0319(3) Uani 1 1 d .
S4 S 0.61947(18) 0.63544(8) 0.63500(9) 0.0408(3) Uani 1 1 d .
S2 S 0.36431(18) 0.87033(8) 0.36623(9) 0.0393(3) Uani 1 1 d .
N4 N 1.1179(5) 0.7742(2) 0.5610(3) 0.0331(8) Uani 1 1 d .
N2 N 0.8819(5) 0.7316(2) 0.3091(3) 0.0328(8) Uani 1 1 d .
C8 C 0.7037(7) 0.8238(3) 0.6141(3) 0.0356(10) Uani 1 1 d .
H8 H 0.5679 0.8405 0.6318 0.043 Uiso 1 1 calc R
C3 C 0.4742(7) 0.6821(3) 0.3684(3) 0.0381(11) Uani 1 1 d .
H3 H 0.3407 0.6654 0.3883 0.046 Uiso 1 1 calc R
C2 C 0.5248(6) 0.7739(3) 0.3544(3) 0.0285(9) Uani 1 1 d .
C6 C 0.9733(6) 0.7120(3) 0.5823(3) 0.0246(8) Uani 1 1 d .
N1 N 0.5391(6) 0.9515(2) 0.3425(3) 0.0397(9) Uani 1 1 d .
C7 C 0.7654(6) 0.7327(3) 0.6092(3) 0.0291(9) Uani 1 1 d .
C1 C 0.7303(6) 0.7944(3) 0.3259(3) 0.0250(9) Uani 1 1 d .
C10 C 1.0550(7) 0.8623(3) 0.5663(3) 0.0336(10) Uani 1 1 d .
H10 H 1.1525 0.9080 0.5524 0.040 Uiso 1 1 calc R
C4 C 0.6284(7) 0.6167(3) 0.3521(3) 0.0375(11) Uani 1 1 d .
H4 H 0.5993 0.5546 0.3602 0.045 Uiso 1 1 calc R
C9 C 0.8526(8) 0.8891(3) 0.5916(3) 0.0377(11) Uani 1 1 d .
H9 H 0.8170 0.9513 0.5934 0.045 Uiso 1 1 calc R
C5 C 0.8285(7) 0.6439(3) 0.3232(3) 0.0391(11) Uani 1 1 d .
H5 H 0.9304 0.5985 0.3133 0.047 Uiso 1 1 calc R
N3 N 0.7909(6) 0.5551(2) 0.6085(3) 0.0427(10) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S3 0.0317(6) 0.0246(6) 0.0440(7) -0.0028(5) 0.0104(5) 0.0017(4)
S1 0.0263(5) 0.0242(6) 0.0466(7) -0.0003(5) 0.0101(4) 0.0016(4)
S4 0.0261(6) 0.0384(7) 0.0603(8) 0.0036(6) 0.0140(5) -0.0074(5)
S2 0.0301(6) 0.0386(7) 0.0541(8) 0.0020(5) 0.0207(5) 0.0098(5)
N4 0.0243(19) 0.034(2) 0.043(2) 0.0011(17) 0.0127(15) -0.0023(15)
N2 0.0258(19) 0.0298(19) 0.045(2) 0.0041(17) 0.0108(15) 0.0054(15)
C8 0.024(2) 0.041(3) 0.044(3) 0.000(2) 0.0125(19) 0.0081(19)
C3 0.029(2) 0.043(3) 0.042(3) 0.005(2) 0.0030(19) 0.000(2)
C2 0.019(2) 0.036(2) 0.031(2) 0.0017(18) 0.0061(16) 0.0005(17)
C6 0.024(2) 0.023(2) 0.027(2) 0.0003(16) 0.0049(16) 0.0034(16)
N1 0.036(2) 0.0290(19) 0.059(3) -0.0037(18) 0.0197(18) 0.0098(16)
C7 0.020(2) 0.035(2) 0.033(2) 0.0011(19) 0.0077(16) -0.0015(17)
C1 0.022(2) 0.024(2) 0.030(2) -0.0012(17) 0.0064(16) 0.0002(15)
C10 0.034(2) 0.034(2) 0.035(2) -0.0019(19) 0.0127(18) -0.0099(19)
C4 0.039(3) 0.023(2) 0.047(3) 0.003(2) -0.004(2) -0.0031(19)
C9 0.048(3) 0.022(2) 0.044(3) 0.0004(19) 0.010(2) 0.0046(19)
C5 0.036(3) 0.030(2) 0.049(3) -0.007(2) 0.004(2) 0.005(2)
N3 0.040(2) 0.031(2) 0.059(3) -0.0029(19) 0.0137(18) -0.0088(17)
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 98.95(19)
N1 S1 C1 99.29(19)
N3 S4 C7 99.75(19)
N1 S2 C2 99.74(19)
C6 N4 C10 115.7(3)
C5 N2 C1 115.6(4)
C7 C8 C9 117.1(4)
C4 C3 C2 117.9(4)
C3 C2 C1 118.1(4)
C3 C2 S2 128.6(3)
C1 C2 S2 113.4(3)
N4 C6 C7 124.6(4)
N4 C6 S3 121.9(3)
C7 C6 S3 113.5(3)
S1 N1 S2 114.2(2)
C8 C7 C6 118.7(4)
C8 C7 S4 128.2(3)
C6 C7 S4 113.0(3)
N2 C1 C2 124.9(4)
N2 C1 S1 121.8(3)
C2 C1 S1 113.3(3)
N4 C10 C9 123.6(4)
C3 C4 C5 119.8(4)
C8 C9 C10 120.2(4)
N2 C5 C4 123.7(4)
S4 N3 S3 114.6(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S3 N3 1.658(4)
S3 C6 1.745(4)
S1 N1 1.653(4)
S1 C1 1.744(4)
S4 N3 1.646(4)
S4 C7 1.737(4)
S2 N1 1.655(4)
S2 C2 1.730(4)
N4 C6 1.328(5)
N4 C10 1.342(5)
N2 C5 1.337(5)
N2 C1 1.343(5)
C8 C7 1.382(6)
C8 C9 1.382(6)
C3 C4 1.379(6)
C3 C2 1.390(6)
C2 C1 1.401(5)
C6 C7 1.407(5)
C10 C9 1.388(6)
C4 C5 1.397(6)
