#------------------------------------------------------------------------------
#$Date: 2015-05-13 23:46:06 +0300 (Wed, 13 May 2015) $
#$Revision: 136450 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/06/2240667.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_2240667
loop_
_publ_author_name
'Setifi, Zouaoui'
'Valkonen, Arto'
'Fernandes, Manuel A.'
'Nummelin, Sami'
'Boughzala, Habib'
'Setifi, Fatima'
'Glidewell, Christopher'
_publ_section_title
;
 Crystal structures of 2,2'-bipyridin-1-ium
 1,1,3,3-tetracyano-2-ethoxyprop-2-en-1-ide and bis(2,2'-bipyridin-1-ium)
 1,1,3,3-tetracyano-2-(dicyanomethylene)propane-1,3-diide
;
_journal_coeditor_code           HB7404
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              509
_journal_page_last               515
_journal_paper_doi               10.1107/S2056989015007306
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C10 H9 N2 +, C9 H5 N4 O -'
_chemical_formula_moiety         'C10 H9 N2 +, C9 H5 N4 O -'
_chemical_formula_sum            'C19 H14 N6 O'
_chemical_formula_weight         342.36
_chemical_name_systematic
;
2,2'-Bipyridin-1-ium 1,1,3,3-tetracyano-2-ethoxyprop-2-en-1-ide
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                100.0200(10)
_cell_angle_beta                 104.3720(10)
_cell_angle_gamma                92.5900(10)
_cell_formula_units_Z            2
_cell_length_a                   7.25140(10)
_cell_length_b                   10.6647(2)
_cell_length_c                   11.5619(2)
_cell_measurement_reflns_used    4152
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      28.302
_cell_measurement_theta_min      2.912
_cell_volume                     849.27(3)
_computing_cell_refinement
;
DENZO-SMN (Otwinowski & Minor, 1997)
;
_computing_data_collection
;
COLLECT (Bruker, 2008)
;
_computing_data_reduction
;
DENZO-SMN (Otwinowski & Minor, 1997)
;
_computing_molecular_graphics
;
PLATON (Spek, 2009)
;
_computing_publication_material
;
SHELXL2014  (Sheldrick, 2015) and PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR2011 (Burla et al.,  2012)
;
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ  & ω scans'
_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  0.0170
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6234
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.302
_diffrn_reflns_theta_min         2.912
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 2003)
;
_exptl_crystal_colour            'pale orange'
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       plate
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.197
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         4152
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0419
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0362P)²+0.2911P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1029
_reflns_number_gt                3447
_reflns_number_total             4152
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb7404sup1.cif
_cod_data_source_block           I
_cod_database_code               2240667
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.965
_shelx_estimated_absorpt_t_max   0.989
_shelxl_version_number           2.014
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N11 0.21857(15) 0.52707(9) 0.43771(10) 0.0285(2) Uani d 1 . .
H H11 0.304(2) 0.5526(14) 0.5105(14) 0.034 Uiso d 1 . .
C C12 0.13048(16) 0.40769(10) 0.41532(11) 0.0250(2) Uani d 1 . .
C C13 -0.00916(18) 0.36846(12) 0.30713(11) 0.0300(3) Uani d 1 . .
H H13 -0.0760 0.2858 0.2891 0.036 Uiso calc 1 . .
C C14 -0.0511(2) 0.45071(13) 0.22510(12) 0.0354(3) Uani d 1 . .
H H14 -0.1463 0.4240 0.1505 0.042 Uiso calc 1 . .
C C15 0.0455(2) 0.57160(13) 0.25183(13) 0.0370(3) Uani d 1 . .
H H15 0.0191 0.6278 0.1956 0.044 Uiso calc 1 . .
C C16 0.18018(19) 0.60851(12) 0.36102(13) 0.0347(3) Uani d 1 . .
H H16 0.2459 0.6917 0.3820 0.042 Uiso calc 1 . .
N N21 0.33192(15) 0.39123(10) 0.60741(9) 0.0298(2) Uani d 1 . .
C C22 0.19143(16) 0.33195(11) 0.51119(10) 0.0248(2) Uani d 1 . .
C C23 0.10772(18) 0.20973(12) 0.50218(12) 0.0316(3) Uani d 1 . .
H H23 0.0098 0.1704 0.4324 0.038 Uiso calc 1 . .
C C24 0.1711(2) 0.14670(12) 0.59796(13) 0.0358(3) Uani d 1 . .
H H24 0.1167 0.0631 0.5949 0.043 Uiso calc 1 . .
C C25 0.31365(19) 0.20658(13) 0.69753(12) 0.0336(3) Uani d 1 . .
H H25 0.3585 0.1656 0.7645 0.040 Uiso calc 1 . .
C C26 0.39027(18) 0.32811(13) 0.69780(12) 0.0334(3) Uani d 1 . .
H H26 0.4898 0.3686 0.7662 0.040 Uiso calc 1 . .
C C31 0.63575(17) 0.92545(11) 0.75796(11) 0.0258(2) Uani d 1 . .
C C32 0.66992(16) 0.94146(11) 0.88432(11) 0.0243(2) Uani d 1 . .
C C33 0.73776(16) 1.05351(11) 0.97022(10) 0.0252(2) Uani d 1 . .
C C311 0.52991(19) 0.81335(12) 0.68277(12) 0.0327(3) Uani d 1 . .
N N311 0.4472(2) 0.72078(12) 0.62292(12) 0.0525(4) Uani d 1 . .
C C312 0.69653(17) 1.01940(11) 0.69840(11) 0.0278(3) Uani d 1 . .
N N312 0.74430(19) 1.09353(11) 0.64791(11) 0.0396(3) Uani d 1 . .
C C331 0.78777(17) 1.04922(11) 1.09671(11) 0.0281(3) Uani d 1 . .
N N331 0.83067(17) 1.05186(11) 1.19987(10) 0.0365(3) Uani d 1 . .
C C332 0.74824(17) 1.17768(11) 0.94263(11) 0.0277(2) Uani d 1 . .
N N332 0.75833(18) 1.28170(10) 0.92815(10) 0.0366(3) Uani d 1 . .
O O321 0.62639(12) 0.83982(8) 0.93268(8) 0.0279(2) Uani d 0.634(9) A -1
C C321 0.7550(4) 0.7422(3) 0.9381(5) 0.0381(9) Uani d 0.634(9) A -1
H H32A 0.8632 0.7663 1.0117 0.046 Uiso calc 0.634(9) A -1
H H32B 0.8069 0.7308 0.8658 0.046 Uiso calc 0.634(9) A -1
C C322 0.6481(8) 0.6213(3) 0.9417(6) 0.0430(11) Uani d 0.634(9) A -1
H H32C 0.7343 0.5530 0.9458 0.064 Uiso calc 0.634(9) A -1
H H32D 0.5422 0.5977 0.8681 0.064 Uiso calc 0.634(9) A -1
H H32E 0.5974 0.6334 1.0135 0.064 Uiso calc 0.634(9) A -1
O O341 0.62639(12) 0.83982(8) 0.93268(8) 0.0279(2) Uani d 0.366(9) A -2
C C341 0.6787(17) 0.7134(5) 0.8864(6) 0.051(2) Uani d 0.366(9) A -2
H H34A 0.8019 0.7218 0.8647 0.061 Uiso calc 0.366(9) A -2
H H34B 0.5796 0.6712 0.8125 0.061 Uiso calc 0.366(9) A -2
C C342 0.6957(17) 0.6360(6) 0.9825(6) 0.0423(18) Uani d 0.366(9) A -2
H H42C 0.7350 0.5519 0.9541 0.063 Uiso calc 0.366(9) A -2
H H42D 0.5718 0.6252 1.0010 0.063 Uiso calc 0.366(9) A -2
H H42E 0.7914 0.6796 1.0560 0.063 Uiso calc 0.366(9) A -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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C16 N11 C12 123.83(12) ?
C16 N11 H11 119.5(10) ?
C12 N11 H11 116.6(10) ?
N11 C12 C13 117.84(11) ?
N11 C12 C22 116.02(11) ?
C13 C12 C22 126.13(10) ?
C12 C13 C14 119.62(12) ?
C12 C13 H13 120.2 ?
C14 C13 H13 120.2 ?
C15 C14 C13 120.18(13) ?
C15 C14 H14 119.9 ?
C13 C14 H14 119.9 ?
C16 C15 C14 118.72(12) ?
C16 C15 H15 120.6 ?
C14 C15 H15 120.6 ?
N11 C16 C15 119.78(12) ?
N11 C16 H16 120.1 ?
C15 C16 H16 120.1 ?
C26 N21 C22 117.27(11) ?
N21 C22 C23 123.22(11) ?
N21 C22 C12 114.70(10) ?
C23 C22 C12 122.08(11) ?
C24 C23 C22 118.13(12) ?
C24 C23 H23 120.9 ?
C22 C23 H23 120.9 ?
C25 C24 C23 119.32(12) ?
C25 C24 H24 120.3 ?
C23 C24 H24 120.3 ?
C24 C25 C26 118.46(12) ?
C24 C25 H25 120.8 ?
C26 C25 H25 120.8 ?
N21 C26 C25 123.59(12) ?
N21 C26 H26 118.2 ?
C25 C26 H26 118.2 ?
C32 C31 C311 119.84(11) y
C32 C31 C312 123.31(10) y
C311 C31 C312 116.80(11) y
N311 C311 C31 178.44(17) y
N312 C312 C31 178.53(13) y
N331 C331 C33 176.77(13) y
N332 C332 C33 175.54(13) y
C32 C33 C331 119.94(10) y
C32 C33 C332 124.72(11) y
C331 C33 C332 115.15(10) y
C31 C32 C33 127.46(10) y
O321 C32 C31 118.45(10) y
O321 C32 C33 114.02(10) y
C32 O321 C321 117.18(14) ?
O321 C321 C322 108.2(3) ?
O321 C321 H32A 110.1 ?
C322 C321 H32A 110.1 ?
O321 C321 H32B 110.1 ?
C322 C321 H32B 110.1 ?
H32A C321 H32B 108.4 ?
C321 C322 H32C 109.5 ?
C321 C322 H32D 109.5 ?
H32C C322 H32D 109.5 ?
C321 C322 H32E 109.5 ?
H32C C322 H32E 109.5 ?
H32D C322 H32E 109.5 ?
C342 C341 H34A 110.0 ?
C342 C341 H34B 110.0 ?
H34A C341 H34B 108.4 ?
C341 C342 H42C 109.5 ?
C341 C342 H42D 109.5 ?
H42C C342 H42D 109.5 ?
C341 C342 H42E 109.5 ?
H42C C342 H42E 109.5 ?
H42D C342 H42E 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N11 C16 1.3361(17) ?
N11 C12 1.3512(14) ?
N11 H11 0.901(16) ?
C12 C13 1.3842(17) ?
C12 C22 1.4755(17) ?
C13 C14 1.3900(18) ?
C13 H13 0.9500 ?
C14 C15 1.3860(19) ?
C14 H14 0.9500 ?
C15 C16 1.372(2) ?
C15 H15 0.9500 ?
C16 H16 0.9500 ?
N21 C26 1.3325(17) ?
N21 C22 1.3451(15) ?
C22 C23 1.3886(16) ?
C23 C24 1.3870(18) ?
C23 H23 0.9500 ?
C24 C25 1.3767(19) ?
C24 H24 0.9500 ?
C25 C26 1.3861(18) ?
C25 H25 0.9500 ?
C26 H26 0.9500 ?
C31 C32 1.3982(17) y
C32 C33 1.3956(16) y
C31 C311 1.4136(16) y
C31 C312 1.4224(16) y
C33 C331 1.4261(17) y
C33 C332 1.4181(16) y
C32 O321 1.3618(13) y
O321 C321 1.428(2) y
C311 N311 1.1471(17) y
C312 N312 1.1498(16) y
C331 N331 1.1504(16) y
C332 N332 1.1522(16) y
C321 C322 1.487(3) ?
C321 H32A 0.9900 ?
C321 H32B 0.9900 ?
C322 H32C 0.9800 ?
C322 H32D 0.9800 ?
C322 H32E 0.9800 ?
C341 C342 1.480(4) ?
C341 H34A 0.9900 ?
C341 H34B 0.9900 ?
C342 H42C 0.9800 ?
C342 H42D 0.9800 ?
C342 H42E 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
_geom_hbond_publ_flag
N11 H11 N21 . 0.901(15) 2.202(15) 2.6306(15) 108.5(12) y
N11 H11 N311 . 0.901(15) 2.082(15) 2.8268(17) 139.2(13) y
C13 H13 N331 1_444 0.95 2.52 3.4294(18) 160 y
C16 H16 N312 2_676 0.95 2.38 3.2238(18) 148 y
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
_geom_torsion_publ_flag
C16 N11 C12 C13 -0.79(17) ?
C16 N11 C12 C22 -179.72(10) ?
N11 C12 C13 C14 1.28(17) ?
C22 C12 C13 C14 -179.92(11) ?
C12 C13 C14 C15 -0.39(19) ?
C13 C14 C15 C16 -1.02(19) ?
C12 N11 C16 C15 -0.64(18) ?
C14 C15 C16 N11 1.53(19) ?
C26 N21 C22 C23 -0.53(17) ?
C26 N21 C22 C12 178.83(10) ?
N11 C12 C22 N21 -1.88(15) ?
C13 C12 C22 N21 179.30(11) ?
N11 C12 C22 C23 177.49(11) ?
C13 C12 C22 C23 -1.34(18) ?
N21 C22 C23 C24 0.76(19) ?
C12 C22 C23 C24 -178.54(11) ?
C22 C23 C24 C25 -0.2(2) ?
C23 C24 C25 C26 -0.6(2) ?
C22 N21 C26 C25 -0.31(18) ?
C24 C25 C26 N21 0.9(2) ?
C311 C31 C32 O321 10.27(17) ?
C312 C31 C32 O321 -172.13(11) ?
O321 C32 C33 C331 11.01(16) ?
O321 C32 C33 C332 -163.73(11) ?
C31 C32 C33 C331 -171.92(11) y
C31 C32 C33 C332 13.3(2) y
C33 C32 C31 C311 -166.68(12) y
C33 C32 C31 C312 10.92(19) y
C31 C32 O321 C321 76.5(3) y
C33 C32 O321 C321 -106.2(3) y
C32 O321 C321 C322 -156.1(4) y

_cod_database_fobs_code 2240667
