#------------------------------------------------------------------------------
#$Date: 2016-02-21 01:03:34 +0100 (dom 21 de feb de 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/67/2236787.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_2236787
loop_
_publ_author_name
'Ziegler, Christopher J.'
'Nemykin, Victor N.'
_publ_section_title
;
 2,5-Diaminothiophene-3,4-dicarbonitrile
;
_journal_coeditor_code           ZS2223
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2693
_journal_paper_doi               10.1107/S1600536812034678
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C6 H4 N4 S'
_chemical_formula_moiety         'C6 H4 N4 S'
_chemical_formula_sum            'C6 H4 N4 S'
_chemical_formula_weight         164.19
_chemical_melting_point          513
_chemical_name_common            2,5-diamino-3,4-dicyanothiophene
_chemical_name_systematic        2,5-Diaminothiophene-3,4-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_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.9231(2)
_cell_length_b                   13.8213(12)
_cell_length_c                   12.6465(11)
_cell_measurement_reflns_used    783
_cell_measurement_temperature    123
_cell_measurement_theta_max      27
_cell_measurement_theta_min      2
_cell_volume                     685.72(9)
_computing_cell_refinement       'HKL-2000 (Otwinowski & Minor, 1997)'
_computing_data_collection       'CrystalClear (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear (Rigaku, 2009)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       Serial
_diffrn_measurement_device_type  'Rigaku RAPID II'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Mo Ka'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.054
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2260
_diffrn_reflns_theta_full        26.931
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         3.360
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_time  2
_diffrn_standards_number         783
_exptl_absorpt_coefficient_mu    0.398
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.590
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.65
_refine_diff_density_min         -0.63
_refine_ls_extinction_coef       0.0
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9931
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     51
_refine_ls_number_reflns         769
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0530
_refine_ls_shift/su_max          0.0000992
_refine_ls_shift/su_mean         0.0000128
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994; Prince, 1982)
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)]
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax
 Method = Robust Weighting (Prince, 1982)
 W = [weight] * [1-(deltaF/6*sigmaF)²]²
 Ai are:  57.9 74.5 21.5
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1162
_refine_ls_wR_factor_gt          0.0845
_refine_ls_wR_factor_ref         0.1162
_reflns_number_gt                492
_reflns_number_total             783
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zs2223.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P b c n '
_cod_database_code               2236787
_cod_database_fobs_code          2236787
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,z
x+1/2,-y+1/2,-z
x,-y,z+1/2
-x,y,-z+1/2
-x+1/2,-y+1/2,z+1/2
x+1/2,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_occupancy
S S1 1.0000 0.75078(10) 0.7500 0.0189 Uani 1.0000
C C1 0.8517(10) 0.6628(3) 0.6618(3) 0.0184 Uani 1.0000
N N1 0.7035(9) 0.6908(2) 0.5697(2) 0.0205 Uani 1.0000
H H2 0.6326 0.6473 0.5246 0.0500 Uiso 1.0000
H H1 0.6790 0.7530 0.5557 0.0500 Uiso 1.0000
C C2 0.9146(10) 0.5716(3) 0.6988(3) 0.0188 Uani 1.0000
C C3 0.8190(10) 0.4873(3) 0.6416(3) 0.0211 Uani 1.0000
N N2 0.7390(11) 0.4203(2) 0.5938(3) 0.0286 Uani 1.0000
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 0.0243(7) 0.0137(5) 0.0188(6) 0.0000 -0.0041(6) 0.0000
C1 0.0202(19) 0.0184(17) 0.0166(16) -0.0027(16) 0.0025(15) -0.0009(13)
N1 0.0285(19) 0.0152(14) 0.0177(14) 0.0003(14) -0.0060(14) 0.0012(11)
C2 0.023(2) 0.0153(16) 0.0181(17) -0.0018(15) 0.0016(16) -0.0027(14)
C3 0.024(2) 0.0213(19) 0.0176(17) 0.0006(17) -0.0003(16) 0.0021(15)
N2 0.040(2) 0.0205(16) 0.0249(17) -0.0053(17) -0.0034(18) -0.0021(13)
loop_
_atom_type_symbol
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 2.3100 1.0200 1.5886 0.8650 20.8439 10.2075 0.5687 51.6512 0.2156 0.0033
0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.4930 0.3229 0.1402 0.0408 10.5109 26.1257 3.1424 57.7998 0.0030 0.0000
0.0000 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 12.2126 3.1322 2.0125 1.1663 0.0057 9.8933 28.9975 0.5826 -11.5290 0.0061
0.0033 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 6.9053 5.2034 1.4379 1.5863 1.4679 22.2151 0.2536 56.1720 0.8669 0.1246
0.1234 'International Tables Vol C 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
_geom_angle_publ_flag
C1 S1 C1 6_756 91.9(3) no
S1 C1 N1 . 119.4(3) no
S1 C1 C2 . 111.3(3) no
N1 C1 C2 . 129.3(3) no
C1 N1 H2 . 120.0 no
C1 N1 H1 . 119.8 no
H2 N1 H1 . 120.2 no
C2 C2 C1 6_756 112.8(2) no
C2 C2 C3 6_756 125.0(2) no
C1 C2 C3 . 122.3(3) no
C2 C3 N2 . 178.6(4) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C1 6_756 1.750(4) no
S1 C1 . 1.750(4) no
C1 N1 . 1.358(5) no
C1 C2 . 1.367(5) no
N1 H2 . 0.874 no
N1 H1 . 0.884 no
C2 C2 6_756 1.458(7) no
C2 C3 . 1.422(5) no
C3 N2 . 1.149(5) no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H2 N2 2_666 0.87 2.29 3.106(5) 156 yes
N1 H1 N2 3_655 0.88 2.38 3.196(5) 153 yes
