#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/76/2227612.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2227612
loop_
_publ_author_name
'Arman, Hadi D.'
'Kaulgud, Trupta'
'Tiekink, Edward R. T.'
_publ_section_title
;
 Benzoic
 acid--2-{(E)-[(E)-2-(2-pyridylmethylidene)hydrazin-1-ylidene]methyl}pyridine
 (2/1)
;
_journal_coeditor_code           HG2725
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2813
_journal_paper_doi               10.1107/S1600536810040651
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C12 H10 N4, 2C7 H6 O2'
_chemical_formula_moiety         'C12 H10 N4, 2(C7 H6 O2)'
_chemical_formula_sum            'C26 H22 N4 O4'
_chemical_formula_weight         454.48
_chemical_name_systematic
;
Benzoic
acid--2-{(E)-[(E)-2-(2-pyridylmethylidene)hydrazin-1-
ylidene]methyl}pyridine (2/1)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                108.985(6)
_cell_angle_beta                 99.830(9)
_cell_angle_gamma                97.849(10)
_cell_formula_units_Z            1
_cell_length_a                   4.4509(7)
_cell_length_b                   11.3635(17)
_cell_length_c                   12.0612(17)
_cell_measurement_reflns_used    2619
_cell_measurement_temperature    98(2)
_cell_measurement_theta_max      40.2
_cell_measurement_theta_min      2.1
_cell_volume                     556.16(15)
_computing_cell_refinement
'CrystalClear (Molecular Structure Corporation & Rigaku, 2005)'
_computing_data_collection
'CrystalClear (Molecular Structure Corporation & Rigaku, 2005)'
_computing_data_reduction
'CrystalClear (Molecular Structure Corporation & Rigaku, 2005)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      98(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Rigaku AFC12Κ/SATURN724'
_diffrn_measurement_method       ω
_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  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2790
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.11
_diffrn_standards_decay_%        '< 1'
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             238
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.20
_refine_diff_density_min         -0.23
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.00
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         1935
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.00
_refine_ls_R_factor_all          0.045
_refine_ls_R_factor_gt           0.042
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0744P)²+0.1759P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.114
_refine_ls_wR_factor_ref         0.117
_reflns_number_gt                1811
_reflns_number_total             1935
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2725.cif
_cod_data_source_block           I
_cod_original_cell_volume        556.16(14)
_cod_database_code               2227612
_cod_database_fobs_code          2227612
loop_
_symmetry_equiv_pos_as_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_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.6343(3) 0.67141(10) 0.18059(9) 0.0287(3) Uani d D 1 . .
H H1o 0.584(5) 0.692(2) 0.2479(12) 0.050(6) Uiso d D 1 . .
O O2 0.7598(3) 0.88248(10) 0.23009(9) 0.0315(3) Uani d . 1 . .
C C1 0.7523(3) 0.77587(13) 0.16270(12) 0.0235(3) Uani d . 1 . .
C C2 0.8828(3) 0.74881(14) 0.05272(12) 0.0227(3) Uani d . 1 . .
C C3 1.0455(3) 0.85068(14) 0.03269(13) 0.0278(4) Uani d . 1 . .
H H3 1.0702 0.9349 0.0878 0.033 Uiso calc R 1 . .
C C4 1.1716(4) 0.82926(15) -0.06766(14) 0.0311(4) Uani d . 1 . .
H H4 1.2846 0.8987 -0.0809 0.037 Uiso calc R 1 . .
C C5 1.1331(4) 0.70640(15) -0.14890(13) 0.0289(4) Uani d . 1 . .
H H5 1.2192 0.6919 -0.2178 0.035 Uiso calc R 1 . .
C C6 0.9695(4) 0.60477(15) -0.12974(13) 0.0294(4) Uani d . 1 . .
H H6 0.9428 0.5208 -0.1856 0.035 Uiso calc R 1 . .
C C7 0.8444(3) 0.62603(14) -0.02863(13) 0.0263(3) Uani d . 1 . .
H H7 0.7326 0.5564 -0.0152 0.032 Uiso calc R 1 . .
N N1 0.4834(3) 0.73022(11) 0.39929(10) 0.0214(3) Uani d . 1 . .
N N2 0.9261(3) 0.54922(10) 0.52702(10) 0.0211(3) Uani d . 1 . .
C C8 0.6169(3) 0.69350(12) 0.48783(12) 0.0190(3) Uani d . 1 . .
C C9 0.6033(3) 0.75148(13) 0.60760(12) 0.0219(3) Uani d . 1 . .
H H9 0.7002 0.7236 0.6683 0.026 Uiso calc R 1 . .
C C10 0.4469(3) 0.85009(13) 0.63643(12) 0.0233(3) Uani d . 1 . .
H H10 0.4365 0.8918 0.7175 0.028 Uiso calc R 1 . .
C C11 0.3052(3) 0.88738(13) 0.54546(13) 0.0231(3) Uani d . 1 . .
H H11 0.1932 0.9541 0.5627 0.028 Uiso calc R 1 . .
C C12 0.3304(3) 0.82529(13) 0.42883(13) 0.0230(3) Uani d . 1 . .
H H12 0.2344 0.8515 0.3668 0.028 Uiso calc R 1 . .
C C13 0.7833(3) 0.58938(13) 0.45006(12) 0.0209(3) Uani d . 1 . .
H H13 0.7846 0.5516 0.3674 0.025 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'
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
C1 O1 H1o . . 109.1(15) ?
O2 C1 O1 . . 123.44(13) ?
O2 C1 C2 . . 123.29(14) ?
O1 C1 C2 . . 113.26(12) ?
C7 C2 C3 . . 119.91(13) ?
C7 C2 C1 . . 121.78(14) ?
C3 C2 C1 . . 118.31(13) ?
C4 C3 C2 . . 119.96(14) ?
C4 C3 H3 . . 120.0 ?
C2 C3 H3 . . 120.0 ?
C3 C4 C5 . . 120.05(14) ?
C3 C4 H4 . . 120.0 ?
C5 C4 H4 . . 120.0 ?
C6 C5 C4 . . 120.19(14) ?
C6 C5 H5 . . 119.9 ?
C4 C5 H5 . . 119.9 ?
C5 C6 C7 . . 119.84(14) ?
C5 C6 H6 . . 120.1 ?
C7 C6 H6 . . 120.1 ?
C2 C7 C6 . . 120.06(14) ?
C2 C7 H7 . . 120.0 ?
C6 C7 H7 . . 120.0 ?
C12 N1 C8 . . 117.83(12) ?
C13 N2 N2 . 2_766 111.87(13) ?
N1 C8 C9 . . 122.45(12) ?
N1 C8 C13 . . 115.34(12) ?
C9 C8 C13 . . 122.20(12) ?
C10 C9 C8 . . 118.85(13) ?
C10 C9 H9 . . 120.6 ?
C8 C9 H9 . . 120.6 ?
C9 C10 C11 . . 119.04(12) ?
C9 C10 H10 . . 120.5 ?
C11 C10 H10 . . 120.5 ?
C10 C11 C12 . . 118.57(12) ?
C10 C11 H11 . . 120.7 ?
C12 C11 H11 . . 120.7 ?
N1 C12 C11 . . 123.25(13) ?
N1 C12 H12 . . 118.4 ?
C11 C12 H12 . . 118.4 ?
N2 C13 C8 . . 120.75(12) ?
N2 C13 H13 . . 119.6 ?
C8 C13 H13 . . 119.6 ?
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
O1 C1 . 1.3292(18) ?
O1 H1o . 0.846(9) ?
O2 C1 . 1.2117(17) ?
C1 C2 . 1.496(2) ?
C2 C7 . 1.388(2) ?
C2 C3 . 1.391(2) ?
C3 C4 . 1.384(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.388(2) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.385(2) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.390(2) ?
C6 H6 . 0.9500 ?
C7 H7 . 0.9500 ?
N1 C12 . 1.3381(18) ?
N1 C8 . 1.3449(18) ?
N2 C13 . 1.2757(18) ?
N2 N2 2_766 1.408(2) ?
C8 C9 . 1.3949(19) ?
C8 C13 . 1.4698(18) ?
C9 C10 . 1.380(2) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.386(2) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.385(2) ?
C11 H11 . 0.9500 ?
C12 H12 . 0.9500 ?
C13 H13 . 0.9500 ?
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
O1 H1o N1 . 0.847(16) 1.881(16) 2.7269(16) 177(2)
C11 H11 O2 2_676 0.95 2.54 3.1811(19) 125
C12 H12 O2 1_455 0.95 2.59 3.4647(19) 154
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
O2 C1 C2 C7 . . . . -173.81(14) ?
O1 C1 C2 C7 . . . . 7.72(19) ?
O2 C1 C2 C3 . . . . 6.0(2) ?
O1 C1 C2 C3 . . . . -172.47(12) ?
C7 C2 C3 C4 . . . . -0.7(2) ?
C1 C2 C3 C4 . . . . 179.52(13) ?
C2 C3 C4 C5 . . . . 0.6(2) ?
C3 C4 C5 C6 . . . . -0.2(2) ?
C4 C5 C6 C7 . . . . -0.2(2) ?
C3 C2 C7 C6 . . . . 0.3(2) ?
C1 C2 C7 C6 . . . . -179.93(13) ?
C5 C6 C7 C2 . . . . 0.2(2) ?
C12 N1 C8 C9 . . . . -0.65(19) ?
C12 N1 C8 C13 . . . . -179.57(11) ?
N1 C8 C9 C10 . . . . 0.1(2) ?
C13 C8 C9 C10 . . . . 178.93(12) ?
C8 C9 C10 C11 . . . . 0.8(2) ?
C9 C10 C11 C12 . . . . -1.0(2) ?
C8 N1 C12 C11 . . . . 0.4(2) ?
C10 C11 C12 N1 . . . . 0.5(2) ?
N2 N2 C13 C8 2_766 . . . -179.13(12) ?
N1 C8 C13 N2 . . . . 178.03(12) ?
C9 C8 C13 N2 . . . . -0.9(2) ?
