#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/36/2233617.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_2233617
loop_
_publ_author_name
'Wang, Na'
'Wang, Jin-Guo'
'Min, An-Jie'
'Fu, Yao-Wen'
_publ_section_title
;
 Bis(4-cyano-1-methylpyridinium)
 bis(1,2-dicyanoethene-1,2-dithiolato-κ²S,S')cuprate(II)
;
_journal_coeditor_code           RZ2689
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m164
_journal_paper_doi               10.1107/S1600536812001377
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          '(C7 H7 N2)2 [Cu (C4 N2 S2)2]'
_chemical_formula_moiety         '2(C7 H7 N2 +), C8 Cu N4 S4 2-'
_chemical_formula_sum            'C22 H14 Cu N8 S4'
_chemical_formula_weight         582.19
_chemical_name_systematic
;
Bis(4-cyano-1-methylpyridinium)
bis(1,2-dicyanoethene-1,2-dithiolato-κ²S,S')cuprate(II)
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                 91.530(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.063(2)
_cell_length_b                   6.9282(14)
_cell_length_c                   15.118(3)
_cell_measurement_reflns_used    2205
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      26.46
_cell_measurement_theta_min      2.70
_cell_volume                     1263.0(4)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0898
_diffrn_reflns_av_sigmaI/netI    0.0643
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6296
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    1.223
_exptl_absorpt_correction_T_max  0.863
_exptl_absorpt_correction_T_min  0.784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            brown-red
_exptl_crystal_density_diffrn    1.531
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             590
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.502
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2418
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0410
_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)+(0.0386P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.1010
_reflns_number_gt                1717
_reflns_number_total             2418
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            rz2689.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               2233617
_cod_database_fobs_code          2233617
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
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
C C1 0.6179(4) 0.7500 0.2599(3) 0.0729(13) Uani d S 1 2
H H1A 0.5519 0.7500 0.2903 0.087 Uiso calc SR 1 2
C C2 0.7158(4) 0.7500 0.3051(3) 0.0713(12) Uani d S 1 2
H H2A 0.7173 0.7500 0.3667 0.086 Uiso calc SR 1 2
C C3 0.8129(3) 0.7500 0.2605(2) 0.0607(11) Uani d S 1 2
C C4 0.8091(3) 0.7500 0.1692(2) 0.0617(11) Uani d S 1 2
H H4A 0.8741 0.7500 0.1374 0.074 Uiso calc SR 1 2
C C5 0.7088(4) 0.7500 0.1267(2) 0.0664(12) Uani d S 1 2
H H5A 0.7051 0.7500 0.0652 0.080 Uiso calc SR 1 2
C C6 0.9162(4) 0.7500 0.3084(3) 0.0741(13) Uani d S 1 2
C C7 0.5079(4) 0.7500 0.1235(3) 0.1021(17) Uani d S 1 2
H H7A 0.4495 0.7500 0.1653 0.153 Uiso d SR 1 2
H H7B 0.5019 0.8631 0.0870 0.153 Uiso d R 1 1
C C8 0.1754(3) 0.0879(5) 0.3350(2) 0.0932(11) Uani d . 1 1
H H8A 0.1563 -0.0273 0.3623 0.112 Uiso calc R 1 1
C C9 0.2320(3) 0.0829(5) 0.2571(2) 0.0982(12) Uani d . 1 1
H H9A 0.2510 -0.0344 0.2317 0.118 Uiso calc R 1 1
C C10 0.2595(3) 0.2500 0.2183(2) 0.0680(12) Uani d S 1 2
C C11 0.3235(4) 0.2500 0.1392(3) 0.1017(19) Uani d S 1 2
C C12 0.0896(4) 0.2500 0.4554(3) 0.0953(17) Uani d S 1 2
H H12A 0.0752 0.3806 0.4730 0.143 Uiso calc PR 0.50 1
H H12B 0.1349 0.1877 0.5001 0.143 Uiso calc PR 0.50 1
H H12C 0.0208 0.1817 0.4482 0.143 Uiso calc PR 0.50 1
C C13 0.8020(3) 0.2500 0.0685(2) 0.0554(10) Uani d S 1 2
C C14 0.7986(3) 0.2500 -0.0259(3) 0.0646(11) Uani d S 1 2
C C15 0.8992(3) 0.2500 0.1138(2) 0.0552(10) Uani d S 1 2
C C16 1.0025(4) 0.2500 0.0683(2) 0.0690(12) Uani d S 1 2
C C17 0.5487(3) 0.2500 0.4089(2) 0.0583(10) Uani d S 1 2
C C18 0.4441(3) 0.2500 0.4523(2) 0.0638(11) Uani d S 1 2
C C19 0.6436(3) 0.2500 0.4574(2) 0.0612(11) Uani d S 1 2
C C20 0.6390(3) 0.2500 0.5519(3) 0.0728(13) Uani d S 1 2
Cu Cu1 0.72603(3) 0.2500 0.26339(3) 0.0546(2) Uani d S 1 2
N N1 0.6152(3) 0.7500 0.1718(2) 0.0664(9) Uani d S 1 2
N N2 0.9963(4) 0.7500 0.3493(3) 0.0960(13) Uani d S 1 2
N N3 0.1483(2) 0.2500 0.3706(2) 0.0610(9) Uani d S 1 2
N N4 0.3757(4) 0.2500 0.0790(3) 0.139(2) Uani d S 1 2
N N5 0.7914(4) 0.2500 -0.1020(2) 0.0927(13) Uani d S 1 2
N N6 1.0837(3) 0.2500 0.0328(2) 0.0997(14) Uani d S 1 2
N N7 0.3600(3) 0.2500 0.4858(2) 0.0807(12) Uani d S 1 2
N N8 0.6352(3) 0.2500 0.6273(2) 0.0951(13) Uani d S 1 2
S S1 0.67434(8) 0.2500 0.11804(6) 0.0613(3) Uani d S 1 2
S S2 0.90748(8) 0.2500 0.22849(6) 0.0623(3) Uani d S 1 2
S S3 0.54354(8) 0.2500 0.29465(6) 0.0699(4) Uani d S 1 2
S S4 0.77358(8) 0.2500 0.41093(6) 0.0713(4) Uani d S 1 2
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'
Cu Cu 0.3201 1.2651 '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
N1 C1 C2 . . 120.3(4)
N1 C1 H1A . . 119.9
C2 C1 H1A . . 119.9
C1 C2 C3 . . 120.0(4)
C1 C2 H2A . . 120.0
C3 C2 H2A . . 120.0
C2 C3 C4 . . 119.2(4)
C2 C3 C6 . . 119.9(4)
C4 C3 C6 . . 120.9(3)
C5 C4 C3 . . 118.6(3)
C5 C4 H4A . . 120.7
C3 C4 H4A . . 120.7
N1 C5 C4 . . 121.0(3)
N1 C5 H5A . . 119.5
C4 C5 H5A . . 119.5
N2 C6 C3 . . 177.4(5)
N1 C7 H7A . . 109.0
N1 C7 H7B . . 109.7
H7A C7 H7B . . 109.5
N3 C8 C9 . . 121.0(3)
N3 C8 H8A . . 119.5
C9 C8 H8A . . 119.5
C10 C9 C8 . . 119.0(3)
C10 C9 H9A . . 120.5
C8 C9 H9A . . 120.5
C9 C10 C9 . 4_565 119.1(4)
C9 C10 C11 . . 120.4(2)
C9 C10 C11 4_565 . 120.4(2)
N4 C11 C10 . . 178.2(5)
N3 C12 H12A . . 109.5
N3 C12 H12B . . 109.5
H12A C12 H12B . . 109.5
N3 C12 H12C . . 109.5
H12A C12 H12C . . 109.5
H12B C12 H12C . . 109.5
C15 C13 C14 . . 120.7(3)
C15 C13 S1 . . 123.7(3)
C14 C13 S1 . . 115.5(3)
N5 C14 C13 . . 177.3(5)
C13 C15 C16 . . 120.8(3)
C13 C15 S2 . . 122.4(3)
C16 C15 S2 . . 116.8(3)
N6 C16 C15 . . 179.8(5)
C19 C17 C18 . . 119.8(3)
C19 C17 S3 . . 123.6(3)
C18 C17 S3 . . 116.6(3)
N7 C18 C17 . . 179.1(4)
C17 C19 C20 . . 119.3(3)
C17 C19 S4 . . 123.1(3)
C20 C19 S4 . . 117.6(3)
N8 C20 C19 . . 179.9(4)
S3 Cu1 S2 . . 178.59(4)
S3 Cu1 S1 . . 87.63(4)
S2 Cu1 S1 . . 90.96(4)
S3 Cu1 S4 . . 90.93(4)
S2 Cu1 S4 . . 90.48(4)
S1 Cu1 S4 . . 178.56(4)
C1 N1 C5 . . 120.9(4)
C1 N1 C7 . . 119.6(4)
C5 N1 C7 . . 119.5(4)
C8 N3 C8 4_565 . 120.9(4)
C8 N3 C12 4_565 . 119.5(2)
C8 N3 C12 . . 119.5(2)
C13 S1 Cu1 . . 101.21(13)
C15 S2 Cu1 . . 101.68(13)
C17 S3 Cu1 . . 101.52(13)
C19 S4 Cu1 . . 100.90(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 N1 . 1.331(5)
C1 C2 . 1.350(6)
C1 H1A . 0.9300
C2 C3 . 1.367(6)
C2 H2A . 0.9300
C3 C4 . 1.380(5)
C3 C6 . 1.424(6)
C4 C5 . 1.354(6)
C4 H4A . 0.9300
C5 N1 . 1.334(5)
C5 H5A . 0.9300
C6 N2 . 1.134(6)
C7 N1 . 1.470(5)
C7 H7A . 0.9589
C7 H7B . 0.9600
C8 N3 . 1.292(4)
C8 C9 . 1.378(4)
C8 H8A . 0.9300
C9 C10 . 1.343(4)
C9 H9A . 0.9300
C10 C9 4_565 1.343(4)
C10 C11 . 1.441(6)
C11 N4 . 1.120(6)
C12 N3 . 1.481(5)
C12 H12A . 0.9600
C12 H12B . 0.9600
C12 H12C . 0.9600
C13 C15 . 1.342(5)
C13 C14 . 1.428(5)
C13 S1 . 1.729(4)
C14 N5 . 1.151(5)
C15 C16 . 1.440(5)
C15 S2 . 1.734(3)
C16 N6 . 1.129(5)
C17 C19 . 1.343(5)
C17 C18 . 1.437(5)
C17 S3 . 1.727(4)
C18 N7 . 1.146(5)
C19 C20 . 1.431(5)
C19 S4 . 1.735(4)
C20 N8 . 1.142(4)
Cu1 S3 . 2.2638(11)
Cu1 S2 . 2.2652(11)
Cu1 S1 . 2.2679(11)
Cu1 S4 . 2.2883(11)
N3 C8 4_565 1.292(4)
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
C1 H1A N8 2_656 0.93 2.60 3.533(6) 179
C2 H2A N7 2_656 0.93 2.44 3.309(6) 156
C5 H5A N4 2_655 0.93 2.36 3.247(6) 159
C8 H8A N2 1_445 0.93 2.48 3.196(5) 134
C9 H9A N5 2_645 0.93 2.51 3.297(4) 143
