#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/79/2227964.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_2227964
loop_
_publ_author_name
'Ding, Yan-Wei'
'Ni, Li-Li'
_publ_section_title
;
 4-Dimethylamino-N'-(3-pyridylmethylidene)benzohydrazide
;
_journal_coeditor_code           RZ2491
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2636
_journal_paper_doi               10.1107/S1600536810037670
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H16 N4 O'
_chemical_formula_moiety         'C15 H16 N4 O'
_chemical_formula_sum            'C15 H16 N4 O'
_chemical_formula_weight         268.32
_chemical_name_systematic
;
4-Dimethylamino-N'-(3-pyridylmethylidene)benzohydrazide
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.513(2)
_cell_length_b                   7.898(2)
_cell_length_c                   30.359(3)
_cell_measurement_reflns_used    1003
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.0
_cell_measurement_theta_min      2.3
_cell_volume                     2760.5(9)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'SMART (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       '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  0.1899
_diffrn_reflns_av_sigmaI/netI    0.1413
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            20776
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.34
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9958
_exptl_absorpt_correction_T_min  0.9915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.247
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.791
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2991
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.791
_refine_ls_R_factor_all          0.1594
_refine_ls_R_factor_gt           0.0584
_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)+(0.0518P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1243
_refine_ls_wR_factor_ref         0.1508
_reflns_number_gt                1163
_reflns_number_total             2991
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz2491.cif
_cod_data_source_block           I
_cod_database_code               2227964
_cod_database_fobs_code          2227964
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, 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_disorder_assembly
_atom_site_disorder_group
N N1 0.7015(2) 0.4212(3) 0.79621(8) 0.0715(8) Uani d . 1 . .
N N2 0.74617(19) 0.2877(3) 0.66360(7) 0.0442(6) Uani d . 1 . .
N N3 0.7654(2) 0.2199(3) 0.62206(7) 0.0462(6) Uani d D 1 . .
N N4 0.8832(2) 0.0665(3) 0.41884(7) 0.0548(7) Uani d . 1 . .
O O1 0.89752(16) 0.4234(2) 0.60695(5) 0.0494(5) Uani d . 1 . .
C C1 0.6436(2) 0.2668(4) 0.73145(8) 0.0425(7) Uani d . 1 . .
C C2 0.5449(3) 0.2126(4) 0.75284(10) 0.0636(9) Uani d . 1 . .
H H2 0.4923 0.1416 0.7387 0.076 Uiso calc R 1 . .
C C3 0.5253(3) 0.2652(4) 0.79551(10) 0.0677(10) Uani d . 1 . .
H H3A 0.4595 0.2296 0.8107 0.081 Uiso calc R 1 . .
C C4 0.6033(3) 0.3691(4) 0.81491(10) 0.0664(10) Uani d . 1 . .
H H4 0.5871 0.4069 0.8433 0.080 Uiso calc R 1 . .
C C5 0.7181(3) 0.3692(4) 0.75487(9) 0.0581(9) Uani d . 1 . .
H H5 0.7854 0.4050 0.7407 0.070 Uiso calc R 1 . .
C C6 0.6688(2) 0.2116(4) 0.68628(9) 0.0459(8) Uani d . 1 . .
H H6 0.6283 0.1210 0.6742 0.055 Uiso calc R 1 . .
C C7 0.8431(2) 0.2965(4) 0.59507(9) 0.0405(7) Uani d . 1 . .
C C8 0.8553(2) 0.2255(3) 0.55060(8) 0.0374(7) Uani d . 1 . .
C C9 0.7769(2) 0.1128(3) 0.53203(8) 0.0416(7) Uani d . 1 . .
H H9 0.7157 0.0732 0.5491 0.050 Uiso calc R 1 . .
C C10 0.7866(2) 0.0575(3) 0.48906(8) 0.0456(7) Uani d . 1 . .
H H10 0.7325 -0.0185 0.4778 0.055 Uiso calc R 1 . .
C C11 0.8776(2) 0.1154(3) 0.46229(9) 0.0423(7) Uani d . 1 . .
C C12 0.9577(2) 0.2268(4) 0.48112(9) 0.0506(8) Uani d . 1 . .
H H12 1.0198 0.2656 0.4643 0.061 Uiso calc R 1 . .
C C13 0.9464(2) 0.2797(3) 0.52384(9) 0.0470(8) Uani d . 1 . .
H H13 1.0012 0.3540 0.5354 0.056 Uiso calc R 1 . .
C C14 0.8071(3) -0.0613(4) 0.40150(9) 0.0736(10) Uani d . 1 . .
H H14A 0.8202 -0.1660 0.4168 0.110 Uiso calc R 1 . .
H H14B 0.8225 -0.0765 0.3707 0.110 Uiso calc R 1 . .
H H14C 0.7279 -0.0266 0.4055 0.110 Uiso calc R 1 . .
C C15 0.9728(3) 0.1326(4) 0.38994(9) 0.0780(11) Uani d . 1 . .
H H15A 0.9755 0.2537 0.3924 0.117 Uiso calc R 1 . .
H H15B 0.9556 0.1018 0.3601 0.117 Uiso calc R 1 . .
H H15C 1.0467 0.0859 0.3982 0.117 Uiso calc R 1 . .
H H3 0.728(2) 0.124(2) 0.6156(9) 0.080 Uiso d D 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
C4 N1 C5 . . 115.3(3) ?
C6 N2 N3 . . 114.8(2) ?
C7 N3 N2 . . 118.8(2) ?
C7 N3 H3 . . 124.4(19) ?
N2 N3 H3 . . 116.7(19) ?
C11 N4 C14 . . 121.3(2) ?
C11 N4 C15 . . 120.8(3) ?
C14 N4 C15 . . 117.7(2) ?
C2 C1 C5 . . 116.9(3) ?
C2 C1 C6 . . 120.8(3) ?
C5 C1 C6 . . 122.3(3) ?
C1 C2 C3 . . 119.0(3) ?
C1 C2 H2 . . 120.5 ?
C3 C2 H2 . . 120.5 ?
C4 C3 C2 . . 118.9(3) ?
C4 C3 H3A . . 120.6 ?
C2 C3 H3A . . 120.6 ?
N1 C4 C3 . . 124.5(3) ?
N1 C4 H4 . . 117.8 ?
C3 C4 H4 . . 117.8 ?
N1 C5 C1 . . 125.3(3) ?
N1 C5 H5 . . 117.4 ?
C1 C5 H5 . . 117.4 ?
N2 C6 C1 . . 120.1(3) ?
N2 C6 H6 . . 119.9 ?
C1 C6 H6 . . 119.9 ?
O1 C7 N3 . . 121.4(3) ?
O1 C7 C8 . . 122.0(3) ?
N3 C7 C8 . . 116.6(3) ?
C9 C8 C13 . . 116.7(2) ?
C9 C8 C7 . . 123.8(2) ?
C13 C8 C7 . . 119.4(3) ?
C10 C9 C8 . . 122.3(2) ?
C10 C9 H9 . . 118.8 ?
C8 C9 H9 . . 118.8 ?
C9 C10 C11 . . 120.3(3) ?
C9 C10 H10 . . 119.8 ?
C11 C10 H10 . . 119.8 ?
N4 C11 C12 . . 122.5(2) ?
N4 C11 C10 . . 119.9(3) ?
C12 C11 C10 . . 117.5(2) ?
C13 C12 C11 . . 121.2(2) ?
C13 C12 H12 . . 119.4 ?
C11 C12 H12 . . 119.4 ?
C12 C13 C8 . . 122.0(3) ?
C12 C13 H13 . . 119.0 ?
C8 C13 H13 . . 119.0 ?
N4 C14 H14A . . 109.5 ?
N4 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
N4 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
N4 C15 H15A . . 109.5 ?
N4 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
N4 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
N1 C4 . 1.331(4) ?
N1 C5 . 1.334(3) ?
N2 C6 . 1.276(3) ?
N2 N3 . 1.388(3) ?
N3 C7 . 1.356(3) ?
N3 H3 . 0.894(10) ?
N4 C11 . 1.376(3) ?
N4 C14 . 1.436(3) ?
N4 C15 . 1.451(3) ?
O1 C7 . 1.236(3) ?
C1 C2 . 1.377(4) ?
C1 C5 . 1.377(4) ?
C1 C6 . 1.468(3) ?
C2 C3 . 1.379(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.352(4) ?
C3 H3A . 0.9300 ?
C4 H4 . 0.9300 ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C8 . 1.469(3) ?
C8 C9 . 1.388(3) ?
C8 C13 . 1.394(3) ?
C9 C10 . 1.380(3) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.402(3) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.397(3) ?
C12 C13 . 1.369(3) ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 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
N3 H3 O1 8_755 0.894(10) 2.159(12) 3.035(3) 166(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 7938586
