#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/73/2227398.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_2227398
loop_
_publ_author_name
'Fan, Chuan-Gang'
'Song, Ming-zhi'
_publ_section_title
;
 N²,N^2'^-Bis(pyridin-2-ylmethylidene)pyridine-2,6-dicarbohydrazide
 dimethylformamide monosolvate
;
_journal_coeditor_code           DS2055
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2766
_journal_paper_doi               10.1107/S1600536810039346
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C19 H15 N7 O2, C3 H7 N1 O1'
_chemical_formula_moiety         'C19 H15 N7 O2, C3 H7 N1 O1'
_chemical_formula_sum            'C22 H22 N8 O3'
_chemical_formula_weight         446.48
_chemical_name_systematic
;
N²,N^2'^-Bis(pyridin-2-ylmethylidene)pyridine-2,6-
dicarbohydrazide dimethylformamide monosolvate
;
_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                 110.826(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.0944(9)
_cell_length_b                   24.639(2)
_cell_length_c                   9.6552(8)
_cell_measurement_reflns_used    2269
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.479
_cell_measurement_theta_min      2.312
_cell_volume                     2244.5(3)
_computing_cell_refinement       'SAINT (Siemens, 2007)'
_computing_data_collection       'SMART (Siemens, 2007)'
_computing_data_reduction        'SAINT (Siemens, 2007)'
_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      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_diffrn_measurement_method       'phi and omega 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  0.0396
_diffrn_reflns_av_sigmaI/netI    0.0486
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11220
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.65
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9844
_exptl_absorpt_correction_T_min  0.9673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.173
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         3945
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0971
_refine_ls_R_factor_gt           0.0448
_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)+(0.0422P)²+0.8005P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0959
_refine_ls_wR_factor_ref         0.1259
_reflns_number_gt                2291
_reflns_number_total             3945
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ds2055.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2227398
_cod_database_fobs_code          2227398
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
N N1 1.0532(2) 0.06010(8) 0.6046(2) 0.0399(5) Uani d . 1 . .
N N2 0.8597(2) 0.13178(8) 0.4467(2) 0.0478(6) Uani d . 1 . .
H H2 0.8437 0.1064 0.5000 0.057 Uiso calc R 1 . .
N N3 0.7529(2) 0.16653(8) 0.3698(2) 0.0468(6) Uani d . 1 . .
N N4 0.3891(2) 0.17800(9) 0.3134(3) 0.0544(6) Uani d . 1 . .
N N5 0.9686(2) -0.00721(8) 0.7745(2) 0.0453(5) Uani d . 1 . .
H H5 0.9187 0.0193 0.7246 0.054 Uiso calc R 1 . .
N N6 0.9148(2) -0.04071(8) 0.8553(2) 0.0446(5) Uani d . 1 . .
N N7 0.5832(2) -0.05299(9) 0.8981(3) 0.0593(7) Uani d . 1 . .
N N8 0.8324(2) 0.16209(9) 0.8702(2) 0.0538(6) Uani d . 1 . .
O O1 1.02185(19) 0.17371(7) 0.3714(2) 0.0590(5) Uani d . 1 . .
O O2 1.1763(2) -0.05273(8) 0.8419(2) 0.0643(6) Uani d . 1 . .
O O3 0.7810(2) 0.09334(7) 0.7038(2) 0.0647(6) Uani d . 1 . .
C C1 0.9891(3) 0.13729(10) 0.4390(3) 0.0435(6) Uani d . 1 . .
C C2 1.0946(3) 0.09502(9) 0.5217(3) 0.0397(6) Uani d . 1 . .
C C3 1.2263(3) 0.09326(10) 0.5094(3) 0.0483(7) Uani d . 1 . .
H H3 1.2512 0.1182 0.4506 0.058 Uiso calc R 1 . .
C C4 1.3202(3) 0.05384(11) 0.5861(3) 0.0564(8) Uani d . 1 . .
H H4 1.4097 0.0516 0.5794 0.068 Uiso calc R 1 . .
C C5 1.2802(3) 0.01771(11) 0.6728(3) 0.0524(7) Uani d . 1 . .
H H5A 1.3422 -0.0092 0.7256 0.063 Uiso calc R 1 . .
C C6 1.1465(3) 0.02221(9) 0.6800(3) 0.0405(6) Uani d . 1 . .
C C7 1.1003(3) -0.01612(10) 0.7739(3) 0.0431(6) Uani d . 1 . .
C C8 0.6315(3) 0.15664(10) 0.3761(3) 0.0489(7) Uani d . 1 . .
H H8 0.6194 0.1272 0.4308 0.059 Uiso calc R 1 . .
C C9 0.5108(3) 0.19145(10) 0.2974(3) 0.0454(7) Uani d . 1 . .
C C10 0.5215(3) 0.23516(11) 0.2119(3) 0.0607(8) Uani d . 1 . .
H H10 0.6081 0.2438 0.2036 0.073 Uiso calc R 1 . .
C C11 0.4044(4) 0.26539(12) 0.1401(3) 0.0659(9) Uani d . 1 . .
H H11 0.4100 0.2950 0.0828 0.079 Uiso calc R 1 . .
C C12 0.2779(3) 0.25150(12) 0.1535(3) 0.0621(8) Uani d . 1 . .
H H12 0.1958 0.2711 0.1044 0.075 Uiso calc R 1 . .
C C13 0.2757(3) 0.20829(12) 0.2407(3) 0.0614(8) Uani d . 1 . .
H H13 0.1899 0.1993 0.2502 0.074 Uiso calc R 1 . .
C C14 0.7866(3) -0.03185(10) 0.8425(3) 0.0466(7) Uani d . 1 . .
H H14 0.7361 -0.0040 0.7815 0.056 Uiso calc R 1 . .
C C15 0.7184(3) -0.06509(10) 0.9230(3) 0.0429(6) Uani d . 1 . .
C C16 0.7895(3) -0.10600(10) 1.0182(3) 0.0495(7) Uani d . 1 . .
H H16 0.8846 -0.1128 1.0347 0.059 Uiso calc R 1 . .
C C17 0.7184(3) -0.13655(11) 1.0882(3) 0.0573(8) Uani d . 1 . .
H H17 0.7637 -0.1647 1.1513 0.069 Uiso calc R 1 . .
C C18 0.5798(3) -0.12467(12) 1.0632(3) 0.0619(8) Uani d . 1 . .
H H18 0.5286 -0.1446 1.1089 0.074 Uiso calc R 1 . .
C C19 0.5177(3) -0.08291(13) 0.9697(4) 0.0680(9) Uani d . 1 . .
H H19 0.4237 -0.0748 0.9550 0.082 Uiso calc R 1 . .
C C20 0.7886(3) 0.11313(12) 0.8238(3) 0.0567(8) Uani d . 1 . .
H H20 0.7607 0.0912 0.8870 0.068 Uiso calc R 1 . .
C C21 0.8856(4) 0.19753(12) 0.7832(4) 0.0753(10) Uani d . 1 . .
H H21A 0.9833 0.1892 0.8016 0.113 Uiso calc R 1 . .
H H21B 0.8776 0.2346 0.8101 0.113 Uiso calc R 1 . .
H H21C 0.8314 0.1924 0.6799 0.113 Uiso calc R 1 . .
C C22 0.8389(4) 0.18074(14) 1.0149(4) 0.0905(12) Uani d . 1 . .
H H22A 0.8091 0.1521 1.0646 0.136 Uiso calc R 1 . .
H H22B 0.7774 0.2115 1.0035 0.136 Uiso calc R 1 . .
H H22C 0.9344 0.1910 1.0724 0.136 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'
O O 0.0106 0.0060 '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'
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
C2 N1 C6 . . 117.6(2) ?
C1 N2 N3 . . 120.0(2) ?
C1 N2 H2 . . 120.0 ?
N3 N2 H2 . . 120.0 ?
C8 N3 N2 . . 116.1(2) ?
C9 N4 C13 . . 116.9(2) ?
C7 N5 N6 . . 119.6(2) ?
C7 N5 H5 . . 120.2 ?
N6 N5 H5 . . 120.2 ?
C14 N6 N5 . . 115.8(2) ?
C15 N7 C19 . . 116.5(2) ?
C20 N8 C21 . . 120.6(2) ?
C20 N8 C22 . . 121.1(3) ?
C21 N8 C22 . . 118.1(3) ?
O1 C1 N2 . . 123.9(2) ?
O1 C1 C2 . . 121.2(2) ?
N2 C1 C2 . . 114.9(2) ?
N1 C2 C3 . . 123.1(2) ?
N1 C2 C1 . . 116.8(2) ?
C3 C2 C1 . . 120.0(2) ?
C4 C3 C2 . . 118.6(2) ?
C4 C3 H3 . . 120.7 ?
C2 C3 H3 . . 120.7 ?
C3 C4 C5 . . 119.2(2) ?
C3 C4 H4 . . 120.4 ?
C5 C4 H4 . . 120.4 ?
C4 C5 C6 . . 118.8(3) ?
C4 C5 H5A . . 120.6 ?
C6 C5 H5A . . 120.6 ?
N1 C6 C5 . . 122.6(2) ?
N1 C6 C7 . . 117.3(2) ?
C5 C6 C7 . . 120.1(2) ?
O2 C7 N5 . . 123.5(2) ?
O2 C7 C6 . . 121.6(2) ?
N5 C7 C6 . . 114.9(2) ?
N3 C8 C9 . . 120.1(2) ?
N3 C8 H8 . . 119.9 ?
C9 C8 H8 . . 119.9 ?
N4 C9 C10 . . 122.2(2) ?
N4 C9 C8 . . 115.2(2) ?
C10 C9 C8 . . 122.6(2) ?
C11 C10 C9 . . 119.5(3) ?
C11 C10 H10 . . 120.3 ?
C9 C10 H10 . . 120.3 ?
C10 C11 C12 . . 119.0(3) ?
C10 C11 H11 . . 120.5 ?
C12 C11 H11 . . 120.5 ?
C13 C12 C11 . . 118.3(3) ?
C13 C12 H12 . . 120.9 ?
C11 C12 H12 . . 120.9 ?
N4 C13 C12 . . 124.2(3) ?
N4 C13 H13 . . 117.9 ?
C12 C13 H13 . . 117.9 ?
N6 C14 C15 . . 120.5(2) ?
N6 C14 H14 . . 119.8 ?
C15 C14 H14 . . 119.8 ?
N7 C15 C16 . . 122.7(2) ?
N7 C15 C14 . . 115.1(2) ?
C16 C15 C14 . . 122.2(2) ?
C17 C16 C15 . . 119.2(2) ?
C17 C16 H16 . . 120.4 ?
C15 C16 H16 . . 120.4 ?
C18 C17 C16 . . 118.6(3) ?
C18 C17 H17 . . 120.7 ?
C16 C17 H17 . . 120.7 ?
C17 C18 C19 . . 118.7(3) ?
C17 C18 H18 . . 120.7 ?
C19 C18 H18 . . 120.7 ?
N7 C19 C18 . . 124.3(3) ?
N7 C19 H19 . . 117.9 ?
C18 C19 H19 . . 117.9 ?
O3 C20 N8 . . 125.9(3) ?
O3 C20 H20 . . 117.0 ?
N8 C20 H20 . . 117.0 ?
N8 C21 H21A . . 109.5 ?
N8 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
N8 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
N8 C22 H22A . . 109.5 ?
N8 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
N8 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 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
N1 C2 . 1.339(3) ?
N1 C6 . 1.342(3) ?
N2 C1 . 1.342(3) ?
N2 N3 . 1.370(3) ?
N2 H2 . 0.8600 ?
N3 C8 . 1.272(3) ?
N4 C9 . 1.333(3) ?
N4 C13 . 1.338(3) ?
N5 C7 . 1.349(3) ?
N5 N6 . 1.373(3) ?
N5 H5 . 0.8600 ?
N6 C14 . 1.275(3) ?
N7 C15 . 1.332(3) ?
N7 C19 . 1.336(3) ?
N8 C20 . 1.308(3) ?
N8 C21 . 1.441(3) ?
N8 C22 . 1.450(4) ?
O1 C1 . 1.222(3) ?
O2 C7 . 1.215(3) ?
O3 C20 . 1.234(3) ?
C1 C2 . 1.500(3) ?
C2 C3 . 1.377(3) ?
C3 C4 . 1.375(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.378(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.380(3) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.494(3) ?
C8 C9 . 1.463(3) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.384(3) ?
C10 C11 . 1.360(4) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.372(4) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.362(4) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
C14 C15 . 1.459(3) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.381(3) ?
C16 C17 . 1.373(3) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.364(4) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.365(4) ?
C18 H18 . 0.9300 ?
C19 H19 . 0.9300 ?
C20 H20 . 0.9300 ?
C21 H21A . 0.9600 ?
C21 H21B . 0.9600 ?
C21 H21C . 0.9600 ?
C22 H22A . 0.9600 ?
C22 H22B . 0.9600 ?
C22 H22C . 0.9600 ?
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
N2 H2 O3 . 0.86 2.29 3.015(3) 141.5
N5 H5 O3 . 0.86 2.26 3.045(3) 152.0
N2 H2 O3 . 0.86 2.29 3.015(3) 141.5
N5 H5 O3 . 0.86 2.26 3.045(3) 152.0
C22 H22A O2 3_757 0.96 2.59 3.469(4) 151.5
C12 H12 O1 4_465 0.93 2.68 3.534(3) 152.9
C11 H11 N4 4_565 0.93 2.62 3.402(4) 142.2
C3 H3 N4 1_655 0.93 2.68 3.585(3) 165.1
C5 H5A N7 1_655 0.93 2.64 3.520(4) 157.9
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656213
