#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/59/2235997.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_2235997
loop_
_publ_author_name
'Novina, J. Josephine'
'Vasuki, G.'
'Karthik, Durai'
'Thomas, K. R. Justin'
_publ_section_title
;
 2,2'-Bithiophene-3,3'-dicarbonitrile
;
_journal_coeditor_code           SU2475
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2542
_journal_paper_doi               10.1107/S1600536812032503
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C10 H4 N2 S2'
_chemical_formula_moiety         'C10 H4 N2 S2'
_chemical_formula_sum            'C10 H4 N2 S2'
_chemical_formula_weight         216.27
_chemical_name_systematic
;
2,2'-Bithiophene-3,3'-dicarbonitrile
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 93.900(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   3.90840(10)
_cell_length_b                   9.8832(4)
_cell_length_c                   12.0091(5)
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      33.53
_cell_measurement_theta_min      2.67
_cell_volume                     462.81(3)
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT and XPREP (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'ω and φ scan'
_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  0.0191
_diffrn_reflns_av_sigmaI/netI    0.0172
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6689
_diffrn_reflns_theta_full        33.53
_diffrn_reflns_theta_max         33.53
_diffrn_reflns_theta_min         2.67
_exptl_absorpt_coefficient_mu    0.528
_exptl_absorpt_correction_T_max  0.900
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             220
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.200
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     64
_refine_ls_number_reflns         1802
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0536P)²+0.0819P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.1047
_reflns_number_gt                1409
_reflns_number_total             1802
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            su2475.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2235997
_cod_database_fobs_code          2235997
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'
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 0.28852(8) 0.68019(3) 0.41382(2) 0.04106(12) Uani d . 1 1
C C1 0.4855(3) 0.57190(12) 0.51077(9) 0.0320(2) Uani d . 1 1
C C2 0.6002(3) 0.64524(13) 0.60413(9) 0.0367(2) Uani d . 1 1
C C5 0.7804(4) 0.59005(15) 0.70133(10) 0.0439(3) Uani d . 1 1
C C4 0.3580(4) 0.81738(13) 0.49772(12) 0.0475(3) Uani d . 1 1
H H4 0.2877 0.9046 0.4781 0.057 Uiso calc R 1 1
C C3 0.5265(4) 0.78545(14) 0.59594(11) 0.0458(3) Uani d . 1 1
H H3 0.5872 0.8480 0.6517 0.055 Uiso calc R 1 1
N N1 0.9252(4) 0.55103(16) 0.77997(11) 0.0630(4) 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 0.0472(2) 0.03822(18) 0.03623(18) 0.00130(11) -0.00859(12) 0.00367(11)
C1 0.0314(4) 0.0354(5) 0.0287(5) -0.0021(4) -0.0009(3) 0.0025(4)
C2 0.0394(6) 0.0387(6) 0.0313(5) -0.0030(5) -0.0020(4) -0.0006(4)
C5 0.0518(7) 0.0431(6) 0.0354(6) -0.0063(5) -0.0073(5) -0.0029(5)
C4 0.0567(8) 0.0339(6) 0.0507(7) 0.0022(5) -0.0053(6) 0.0005(5)
C3 0.0554(8) 0.0380(6) 0.0429(7) -0.0015(5) -0.0044(5) -0.0048(5)
N1 0.0802(10) 0.0599(8) 0.0454(6) -0.0049(7) -0.0218(6) 0.0021(6)
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C4 S1 C1 . . 92.80(6)
C2 C1 C1 . 3_666 129.27(13)
C2 C1 S1 . . 109.09(9)
C1 C1 S1 3_666 . 121.63(11)
C1 C2 C3 . . 113.76(11)
C1 C2 C5 . . 125.17(12)
C3 C2 C5 . . 121.07(11)
N1 C5 C2 . . 177.43(15)
C3 C4 S1 . . 112.37(10)
C3 C4 H4 . . 123.8
S1 C4 H4 . . 123.8
C4 C3 C2 . . 111.98(12)
C4 C3 H3 . . 124.0
C2 C3 H3 . . 124.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
S1 C4 . 1.7000(14)
S1 C1 . 1.7240(11)
C1 C2 . 1.3838(16)
C1 C1 3_666 1.450(2)
C2 C3 . 1.4173(19)
C2 C5 . 1.4298(16)
C5 N1 . 1.1351(17)
C4 C3 . 1.3487(19)
C4 H4 . 0.9300
C3 H3 . 0.9300
