#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/27/2012772.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_2012772
loop_
_publ_author_name
'Toplak, Renata'
'Lorcy, Dominique'
_publ_section_title
;
 A neutral complex of an azino--DTDAF compound with TCNQ
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o370
_journal_page_last               o372
_journal_paper_doi               10.1107/S0108270102007722
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C16 H22 N4 O4 S2 , C12 H4 N4'
_chemical_formula_moiety         'C16 H22 N4 O4 S2 , C12 H4 N4'
_chemical_formula_sum            'C28 H26 N8 O4 S2'
_chemical_formula_weight         602.70
_chemical_name_common
;Ethyl
 2-{[5-(ethoxycarbonyl)-3,4-dimethyl-1,3-thiazol-2(3H)-ylidene]hydrazono}-
3,4-dimethyl-2,3-dihydro-1,3-thiazole-5-carboxylate
7,7,8,8-tetracyano-p-quinodimethane
 (1/1)
;
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90
_cell_angle_beta                 118.67(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   20.960(4)
_cell_length_b                   6.8198(14)
_cell_length_c                   11.730(2)
_cell_measurement_reflns_used    4723
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.9
_cell_measurement_theta_min      2.1
_cell_volume                     1471.2(6)
_computing_cell_refinement       'SELECT and CELL in IPDS'
_computing_data_collection       'EXPOSE in IPDS (Stoe, 1999)'
_computing_data_reduction        'INTEGRATE in IPDS'
_computing_molecular_graphics    'Please provide missing details'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 6.66
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'Stoe IPDS area-detector'
_diffrn_measurement_method       'rotation, φ increment 2°'
_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  0.036
_diffrn_reflns_av_sigmaI/netI    0.036
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7171
_diffrn_reflns_theta_full        26.11
_diffrn_reflns_theta_max         26.11
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'dark purple'
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             628
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.25
_refine_ls_extinction_coef       0.039(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1526
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.970
_refine_ls_R_factor_all          0.057
_refine_ls_R_factor_gt           0.041
_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)+(0.073P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.102
_refine_ls_wR_factor_ref         0.108
_reflns_number_gt                1135
_reflns_number_total             1526
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sk1545.cif
_cod_data_source_block           III
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        1471.2(5)
_cod_original_sg_symbol_H-M      'C 2/m'
_cod_database_code               2012772
_cod_database_fobs_code          2012772
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'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'
loop_
_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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
S1 0.93046(4) 0.0000 0.14076(6) 0.0438(3) Uani d S 1 . . S
N1 0.84242(12) 0.0000 -0.1060(2) 0.0436(6) Uani d S 1 . . N
N2 0.96518(12) 0.0000 -0.0549(2) 0.0450(6) Uani d S 1 . . N
O1 0.74318(12) 0.0000 0.1450(2) 0.0732(8) Uani d S 1 . . O
O2 0.86127(12) 0.0000 0.2948(2) 0.0628(6) Uani d S 1 . . O
C1 0.91603(14) 0.0000 -0.0187(2) 0.0397(6) Uani d S 1 . . C
C2 0.81787(18) 0.0000 -0.2451(3) 0.0654(9) Uani d S 1 . . C
H2A 0.8593 0.0000 -0.2595 0.098 Uiso calc SR 1 . . H
H2B 0.7891 0.1149 -0.2838 0.098 Uiso calc PR 0.50 . . H
H2C 0.7891 -0.1149 -0.2838 0.098 Uiso calc PR 0.50 . . H
C3 0.79813(15) 0.0000 -0.0492(3) 0.0436(6) Uani d S 1 . . C
C4 0.71770(17) 0.0000 -0.1329(3) 0.0621(8) Uani d S 1 . . C
H4A 0.7061 0.0000 -0.2226 0.093 Uiso calc SR 1 . . H
H4B 0.6976 0.1149 -0.1149 0.093 Uiso calc PR 0.50 . . H
H4C 0.6976 -0.1149 -0.1149 0.093 Uiso calc PR 0.50 . . H
C5 0.83581(15) 0.0000 0.0817(3) 0.0440(7) Uani d S 1 . . C
C6 0.80676(17) 0.0000 0.1731(3) 0.0514(7) Uani d S 1 . . C
C7 0.8427(2) 0.0000 0.3991(3) 0.0826(12) Uani d S 1 . . C
H7A 0.8143 -0.1155 0.3936 0.099 Uiso calc PR 0.50 . . H
H7B 0.8143 0.1155 0.3936 0.099 Uiso calc PR 0.50 . . H
C8 0.9117(3) 0.0000 0.5219(4) 0.1019(16) Uani d S 1 . . C
H8A 0.9017 0.0000 0.5937 0.153 Uiso calc SR 1 . . H
H8B 0.9392 0.1149 0.5260 0.153 Uiso calc PR 0.50 . . H
H8C 0.9392 -0.1149 0.5260 0.153 Uiso calc PR 0.50 . . H
N3 0.67704(19) 0.0000 0.4391(3) 0.0955(12) Uani d S 1 . . N
N4 0.44881(17) 0.0000 0.3475(3) 0.0851(11) Uani d S 1 . . N
C9 0.54219(16) 0.0000 0.2641(3) 0.0503(7) Uani d S 1 . . C
C10 0.61769(19) 0.0000 0.3622(3) 0.0631(9) Uani d S 1 . . C
C11 0.49044(17) 0.0000 0.3110(3) 0.0592(9) Uani d S 1 . . C
C12 0.57484(15) 0.0000 0.0888(3) 0.0448(7) Uani d S 1 . . C
H12 0.6241 0.0000 0.1488 0.054 Uiso calc SR 1 . . H
C13 0.52179(14) 0.0000 0.1345(2) 0.0427(6) Uani d S 1 . . C
C14 0.55422(14) 0.0000 -0.0378(2) 0.0452(7) Uani d S 1 . . C
H14 0.5894 0.0000 -0.0645 0.054 Uiso calc SR 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1250 0.1230 '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
C1 S1 C5 . . 89.73(12)
C3 N1 C1 . . 114.4(2)
C3 N1 C2 . . 125.7(2)
C1 N1 C2 . . 119.9(2)
C1 N2 N2 . 5_755 109.8(2)
C6 O2 C7 . . 117.6(3)
N2 C1 N1 . . 122.7(2)
N2 C1 S1 . . 126.7(2)
N1 C1 S1 . . 110.59(18)
N1 C2 H2A . . 109.5
N1 C2 H2B . . 109.5
H2A C2 H2B . . 109.5
N1 C2 H2C . . 109.5
H2A C2 H2C . . 109.5
H2B C2 H2C . . 109.5
C5 C3 N1 . . 112.8(2)
C5 C3 C4 . . 127.5(2)
N1 C3 C4 . . 119.6(2)
C3 C4 H4A . . 109.5
C3 C4 H4B . . 109.5
H4A C4 H4B . . 109.5
C3 C4 H4C . . 109.5
H4A C4 H4C . . 109.5
H4B C4 H4C . . 109.5
C3 C5 C6 . . 127.7(3)
C3 C5 S1 . . 112.43(18)
C6 C5 S1 . . 119.9(2)
O1 C6 O2 . . 124.0(3)
O1 C6 C5 . . 126.2(3)
O2 C6 C5 . . 109.8(2)
O2 C7 C8 . . 106.8(3)
O2 C7 H7A . . 110.4
C8 C7 H7A . . 110.4
O2 C7 H7B . . 110.4
C8 C7 H7B . . 110.4
H7A C7 H7B . . 108.6
C7 C8 H8A . . 109.5
C7 C8 H8B . . 109.5
H8A C8 H8B . . 109.5
C7 C8 H8C . . 109.5
H8A C8 H8C . . 109.5
H8B C8 H8C . . 109.5
C13 C9 C11 . . 122.4(3)
C13 C9 C10 . . 121.7(3)
C11 C9 C10 . . 115.9(3)
N3 C10 C9 . . 179.9(4)
N4 C11 C9 . . 179.5(3)
C14 C12 C13 . . 121.1(2)
C14 C12 H12 . . 119.5
C13 C12 H12 . . 119.5
C9 C13 C14 . 5_655 120.8(2)
C9 C13 C12 . . 121.7(2)
C14 C13 C12 5_655 . 117.5(2)
C12 C14 C13 . 5_655 121.4(3)
C12 C14 H14 . . 119.3
C13 C14 H14 5_655 . 119.3
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 . 1.746(2) yes
S1 C5 . 1.760(3) yes
N1 C3 . 1.378(3) yes
N1 C1 . 1.383(3) yes
N1 C2 . 1.457(4) yes
N2 C1 . 1.289(3) yes
N2 N2 5_755 1.410(5) yes
O1 C6 . 1.209(4) ?
O2 C6 . 1.333(4) ?
O2 C7 . 1.451(3) ?
C2 H2A . 0.9600 ?
C2 H2B . 0.9600 ?
C2 H2C . 0.9600 ?
C3 C5 . 1.349(4) yes
C3 C4 . 1.489(4) ?
C4 H4A . 0.9600 ?
C4 H4B . 0.9600 ?
C4 H4C . 0.9600 ?
C5 C6 . 1.465(4) ?
C7 C8 . 1.473(6) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
N3 C10 . 1.133(4) yes
N4 C11 . 1.142(4) yes
C9 C13 . 1.367(4) yes
C9 C11 . 1.433(4) yes
C9 C10 . 1.443(4) yes
C12 C14 . 1.332(4) yes
C12 C13 . 1.448(4) yes
C12 H12 . 0.9300 ?
C13 C14 5_655 1.446(4) yes
C14 C13 5_655 1.446(4) ?
C14 H14 . 0.9300 ?
