#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/69/2226915.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_2226915
loop_
_publ_author_name
'Gaamoune, Bachir'
'Setifi, Zouaoui'
'Beghidja, Adel'
'El-Ghozzi, Malika'
'Setifi, Fatima'
'Avignant, Daniel'
_publ_section_title
;
 Bis(2,2'-bi-1H-imidazole)copper(II)
 bis(1,1,3,3-tetracyano-2-ethoxypropenide)
;
_journal_coeditor_code           HB5555
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1044
_journal_page_last               m1045
_journal_paper_doi               10.1107/S1600536810029752
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '[Cu (C6 H6 N4)2] (C9 H5 N4 O)2'
_chemical_formula_moiety         'C12 H12 Cu N8 2+, 2(C9 H5 N4 O -)'
_chemical_formula_sum            'C30 H22 Cu N16 O2'
_chemical_formula_weight         702.18
_chemical_name_systematic
;
Bis(2,2'-bi-1H-imidazole)copper(II)
bis(1,1,3,3-tetracyano-2-ethoxypropenide)
;
_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                 117.086(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.1001(8)
_cell_length_b                   26.1834(11)
_cell_length_c                   8.2185(7)
_cell_measurement_reflns_used    3092
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      31.54
_cell_measurement_theta_min      2.78
_cell_volume                     1551.9(3)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_data_collection       'Crysalis CCD (Oxford Diffraction, 2007)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      170(2)
_diffrn_detector_area_resol_mean 8.3622
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0684
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8646
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         2.82
_exptl_absorpt_coefficient_mu    0.763
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_correction_T_min  0.750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2007)'
_exptl_crystal_colour            Green
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             718
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.279
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.933
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3002
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.933
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0340
_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)+(0.0371P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0676
_refine_ls_wR_factor_ref         0.0772
_reflns_number_gt                1854
_reflns_number_total             3002
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5555.cif
_cod_data_source_block           I
_cod_original_cell_volume        1551.9(2)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226915
_cod_database_fobs_code          2226915
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_disorder_assembly
_atom_site_disorder_group
Cu Cu1 0.5000 0.5000 0.5000 0.02739(14) Uani d S 1 . .
O O1 0.5765(2) 0.72753(6) 0.7896(2) 0.0279(4) Uani d . 1 . .
N N1 0.3433(3) 0.55852(7) 0.3669(3) 0.0270(5) Uani d . 1 . .
N N2 0.3432(3) 0.50383(7) 0.6359(2) 0.0250(4) Uani d . 1 . .
N N3 0.1123(3) 0.54298(7) 0.6550(3) 0.0276(5) Uani d . 1 . .
H H3 0.0198 0.5642 0.6311 0.033 Uiso calc R 1 . .
N N4 0.1107(3) 0.60926(7) 0.3218(3) 0.0301(5) Uani d . 1 . .
H H4 0.0189 0.6235 0.3346 0.036 Uiso calc R 1 . .
N N7 0.7829(4) 0.55883(8) 0.7720(3) 0.0473(7) Uani d . 1 . .
N N8 0.3624(4) 0.63047(9) 0.8836(3) 0.0523(7) Uani d . 1 . .
N N9 0.8650(3) 0.63404(8) 0.4902(3) 0.0431(6) Uani d . 1 . .
N N10 0.9040(3) 0.79164(8) 0.6867(3) 0.0388(6) Uani d . 1 . .
C C1 0.2179(3) 0.57061(8) 0.4219(3) 0.0240(6) Uani d . 1 . .
C C2 0.2177(3) 0.54105(8) 0.5686(3) 0.0235(6) Uani d . 1 . .
C C3 0.3131(4) 0.59086(9) 0.2255(4) 0.0362(7) Uani d . 1 . .
H H3A 0.3820 0.5912 0.1579 0.043 Uiso calc R 1 . .
C C4 0.1704(4) 0.62228(9) 0.1967(4) 0.0365(7) Uani d . 1 . .
H H4A 0.1211 0.6484 0.1069 0.044 Uiso calc R 1 . .
C C5 0.3157(4) 0.48229(9) 0.7740(3) 0.0306(6) Uani d . 1 . .
H H5 0.3858 0.4548 0.8490 0.037 Uiso calc R 1 . .
C C6 0.1746(3) 0.50594(9) 0.7877(3) 0.0306(6) Uani d . 1 . .
H H6 0.1278 0.4985 0.8721 0.037 Uiso calc R 1 . .
C C7 0.7098(4) 0.59593(10) 0.7744(3) 0.0312(7) Uani d . 1 . .
C C8 0.4741(4) 0.63526(9) 0.8363(3) 0.0335(7) Uani d . 1 . .
C C9 0.8243(4) 0.66396(10) 0.5669(4) 0.0297(6) Uani d . 1 . .
C C10 0.8449(3) 0.75144(10) 0.6727(3) 0.0286(6) Uani d . 1 . .
C C11 0.6541(3) 0.68945(8) 0.7366(3) 0.0234(6) Uani d . 1 . .
C C12 0.6126(3) 0.64089(8) 0.7755(3) 0.0255(6) Uani d . 1 . .
C C13 0.7714(3) 0.70132(8) 0.6596(3) 0.0241(6) Uani d . 1 . .
C C14 0.4716(3) 0.76732(9) 0.6587(3) 0.0303(6) Uani d . 1 . .
H H14A 0.5344 0.7762 0.5836 0.036 Uiso calc R 1 . .
H H14B 0.4669 0.7984 0.7252 0.036 Uiso calc R 1 . .
C C15 0.2811(4) 0.74960(11) 0.5388(4) 0.0507(8) Uani d . 1 . .
H H15A 0.2125 0.7766 0.4517 0.076 Uiso calc R 1 . .
H H15B 0.2185 0.7413 0.6132 0.076 Uiso calc R 1 . .
H H15C 0.2860 0.7191 0.4720 0.076 Uiso calc R 1 . .
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'
O O 0.0106 0.0060 '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'
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
_geom_angle_publ_flag
N1 Cu1 N1 . 3_666 180.00 ?
N1 Cu1 N2 . 3_666 97.96(8) ?
N1 Cu1 N2 3_666 3_666 82.04(8) ?
N1 Cu1 N2 . . 82.04(8) yes
N1 Cu1 N2 3_666 . 97.96(8) ?
N2 Cu1 N2 3_666 . 180.0 ?
N1 Cu1 N7 . . 95.79(7) n
N1 Cu1 N7 3_666 . 84.21(7) ?
N2 Cu1 N7 3_666 . 88.69(7) ?
N2 Cu1 N7 . . 91.31(7) n
C11 O1 C14 . . 119.25(18) ?
C1 N1 C3 . . 105.9(2) ?
C1 N1 Cu1 . . 113.35(16) ?
C3 N1 Cu1 . . 140.66(17) ?
C2 N2 C5 . . 105.23(19) ?
C2 N2 Cu1 . . 110.87(15) ?
C5 N2 Cu1 . . 143.89(17) ?
C2 N3 C6 . . 107.6(2) ?
C2 N3 H3 . . 126.2 ?
C6 N3 H3 . . 126.2 ?
C1 N4 C4 . . 107.3(2) ?
C1 N4 H4 . . 126.3 ?
C4 N4 H4 . . 126.3 ?
C7 N7 Cu1 . . 103.7(2) ?
N1 C1 N4 . . 110.7(2) ?
N1 C1 C2 . . 116.9(2) ?
N4 C1 C2 . . 132.4(2) ?
N2 C2 N3 . . 111.0(2) ?
N2 C2 C1 . . 116.8(2) ?
N3 C2 C1 . . 132.2(2) ?
C4 C3 N1 . . 109.5(2) ?
C4 C3 H3A . . 125.2 ?
N1 C3 H3A . . 125.2 ?
C3 C4 N4 . . 106.6(2) ?
C3 C4 H4A . . 126.7 ?
N4 C4 H4A . . 126.7 ?
C6 C5 N2 . . 110.0(2) ?
C6 C5 H5 . . 125.0 ?
N2 C5 H5 . . 125.0 ?
C5 C6 N3 . . 106.1(2) ?
C5 C6 H6 . . 126.9 ?
N3 C6 H6 . . 126.9 ?
N7 C7 C12 . . 177.8(3) ?
N8 C8 C12 . . 179.4(3) ?
N9 C9 C13 . . 179.1(3) ?
N10 C10 C13 . . 178.6(3) ?
O1 C11 C12 . . 113.8(2) ?
O1 C11 C13 . . 119.61(19) ?
C12 C11 C13 . . 126.5(2) ?
C11 C12 C7 . . 124.4(2) ?
C11 C12 C8 . . 119.1(2) ?
C7 C12 C8 . . 116.3(2) ?
C11 C13 C9 . . 121.6(2) ?
C11 C13 C10 . . 121.2(2) ?
C9 C13 C10 . . 117.2(2) ?
O1 C14 C15 . . 110.4(2) ?
O1 C14 H14A . . 109.6 ?
C15 C14 H14A . . 109.6 ?
O1 C14 H14B . . 109.6 ?
C15 C14 H14B . . 109.6 ?
H14A C14 H14B . . 108.1 ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
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
Cu1 N1 . 1.9727(19) yes
Cu1 N1 3_666 1.9727(19) ?
Cu1 N2 3_666 2.0397(18) ?
Cu1 N2 . 2.0397(18) yes
Cu1 N7 . 2.821(2) yes
O1 C11 . 1.352(3) ?
O1 C14 . 1.460(3) ?
N1 C1 . 1.324(3) ?
N1 C3 . 1.367(3) ?
N2 C2 . 1.333(3) ?
N2 C5 . 1.374(3) ?
N3 C2 . 1.337(3) ?
N3 C6 . 1.372(3) ?
N3 H3 . 0.8800 ?
N4 C1 . 1.343(3) ?
N4 C4 . 1.364(3) ?
N4 H4 . 0.8800 ?
N7 C7 . 1.143(3) ?
N8 C8 . 1.143(3) ?
N9 C9 . 1.144(3) ?
N10 C10 . 1.140(3) ?
C1 C2 . 1.433(3) ?
C3 C4 . 1.349(3) ?
C3 H3A . 0.9500 ?
C4 H4A . 0.9500 ?
C5 C6 . 1.349(3) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 C12 . 1.419(3) ?
C8 C12 . 1.428(4) ?
C9 C13 . 1.421(3) ?
C10 C13 . 1.425(3) ?
C11 C12 . 1.389(3) ?
C11 C13 . 1.395(3) ?
C14 C15 . 1.477(3) ?
C14 H14A . 0.9900 ?
C14 H14B . 0.9900 ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
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
N3 H3 N9 1_455 0.88 2.22 3.011(3) 149
N4 H4 N9 1_455 0.88 2.17 2.967(3) 150
C3 H3A N8 1_554 0.95 2.42 3.187(3) 138
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N2 Cu1 N1 C1 3_666 . . . 178.54(16) ?
N2 Cu1 N1 C1 . . . . -1.46(16) ?
N7 Cu1 N1 C1 . . . . -91.98(17) ?
N2 Cu1 N1 C3 3_666 . . . 2.7(3) ?
N2 Cu1 N1 C3 . . . . -177.3(3) ?
N7 Cu1 N1 C3 . . . . 92.2(3) ?
N1 Cu1 N2 C2 3_666 . . . -178.76(15) ?
N7 Cu1 N2 C2 . . . . 96.90(16) ?
N1 Cu1 N2 C5 . . . . -178.8(3) ?
N1 Cu1 N2 C5 3_666 . . . 1.2(3) ?
N7 Cu1 N2 C5 . . . . -83.1(3) ?
N1 Cu1 N7 C7 . . . . 24.02(19) ?
N1 Cu1 N7 C7 3_666 . . . -155.98(19) ?
N2 Cu1 N7 C7 3_666 . . . 121.89(19) ?
N2 Cu1 N7 C7 . . . . -58.11(19) ?
C3 N1 C1 N4 . . . . -0.2(3) ?
Cu1 N1 C1 N4 . . . . -177.52(15) ?
C3 N1 C1 C2 . . . . 178.7(2) ?
Cu1 N1 C1 C2 . . . . 1.4(3) ?
C4 N4 C1 N1 . . . . 0.2(3) ?
C4 N4 C1 C2 . . . . -178.6(2) ?
C5 N2 C2 N3 . . . . -1.2(3) ?
Cu1 N2 C2 N3 . . . . 178.75(15) ?
C5 N2 C2 C1 . . . . 179.2(2) ?
Cu1 N2 C2 C1 . . . . -0.8(2) ?
C6 N3 C2 N2 . . . . 1.3(3) ?
C6 N3 C2 C1 . . . . -179.2(2) ?
N1 C1 C2 N2 . . . . -0.4(3) ?
N4 C1 C2 N2 . . . . 178.3(2) ?
N1 C1 C2 N3 . . . . -179.9(2) ?
N4 C1 C2 N3 . . . . -1.2(4) ?
C1 N1 C3 C4 . . . . 0.2(3) ?
Cu1 N1 C3 C4 . . . . 176.3(2) ?
N1 C3 C4 N4 . . . . -0.1(3) ?
C1 N4 C4 C3 . . . . -0.1(3) ?
C2 N2 C5 C6 . . . . 0.7(3) ?
Cu1 N2 C5 C6 . . . . -179.3(2) ?
N2 C5 C6 N3 . . . . 0.1(3) ?
C2 N3 C6 C5 . . . . -0.9(3) ?
C14 O1 C11 C12 . . . . -129.2(2) ?
C14 O1 C11 C13 . . . . 54.0(3) ?
O1 C11 C12 C7 . . . . -164.3(2) ?
C13 C11 C12 C7 . . . . 12.3(4) ?
O1 C11 C12 C8 . . . . 10.1(3) ?
C13 C11 C12 C8 . . . . -173.3(2) ?
O1 C11 C13 C9 . . . . -166.3(2) ?
C12 C11 C13 C9 . . . . 17.2(4) ?
O1 C11 C13 C10 . . . . 14.4(4) ?
C12 C11 C13 C10 . . . . -162.0(2) ?
C11 O1 C14 C15 . . . . 81.6(3) ?
