#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/24/2222411.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_2222411
loop_
_publ_author_name
'Warad, Ismail'
'Al-Nuri, Mohammed'
'Al-Resayes, Saud'
'Al-Farhan, Khalid'
'Ghazzali, Mohamed'
_publ_section_title
;
 N'-(Di-2-pyridylmethylene)benzohydrazide
;
_journal_coeditor_code           NG2595
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1597
_journal_paper_doi               10.1107/S1600536809022090
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C18 H14 N4 O'
_chemical_formula_moiety         'C18 H14 N4 O'
_chemical_formula_sum            'C18 H14 N4 O'
_chemical_formula_weight         302.33
_chemical_name_systematic
;
N'-(Di-2-pyridylmethylene)benzohydrazide
;
_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                 108.974(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2741(5)
_cell_length_b                   22.1436(14)
_cell_length_c                   8.8006(5)
_cell_measurement_reflns_used    880
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      3.00
_cell_volume                     1524.82(16)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2007)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2007)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2007)'
_computing_molecular_graphics
'DIAMOND (Brandenburg, 2006) and PLUTO (Motherwell et al.,  1999)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            33115
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.06
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9885
_exptl_absorpt_correction_T_min  0.9684
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.238
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3491
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.991
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0529
_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)+(0.1092P)²+0.076P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1481
_refine_ls_wR_factor_ref         0.1690
_reflns_number_gt                2329
_reflns_number_total             3491
_reflns_threshold_expression     I>2δ(I)
_cod_data_source_file            ng2595.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1524.82(15)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2222411
_cod_database_fobs_code          2222411
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
O O1 0.17708(18) 0.55123(6) 0.48480(14) 0.0649(4) Uani d . 1 . .
N N1 0.21198(18) 0.51374(6) 0.73562(16) 0.0485(4) Uani d . 1 . .
H H7 0.1902 0.5186 0.8240 0.058 Uiso calc R 1 . .
C C1 0.1073(2) 0.62760(7) 0.8228(2) 0.0513(4) Uani d . 1 . .
H H1 0.1787 0.6045 0.9058 0.062 Uiso calc R 1 . .
N N2 0.29967(18) 0.46379(6) 0.71474(16) 0.0472(3) Uani d . 1 . .
C C2 0.0312(2) 0.67909(8) 0.8581(2) 0.0598(5) Uani d . 1 . .
H H2 0.0526 0.6907 0.9644 0.072 Uiso calc R 1 . .
N N3 0.22378(18) 0.47159(6) 1.01763(16) 0.0509(4) Uani d . 1 . .
C C3 -0.0768(2) 0.71315(8) 0.7347(2) 0.0604(5) Uani d . 1 . .
H H3 -0.1280 0.7477 0.7583 0.072 Uiso calc R 1 . .
N N4 0.4144(2) 0.31839(6) 0.84066(19) 0.0550(4) Uani d . 1 . .
C C4 -0.1087(2) 0.69618(8) 0.5779(2) 0.0590(5) Uani d . 1 . .
H H4 -0.1829 0.7189 0.4956 0.071 Uiso calc R 1 . .
C C5 -0.0308(2) 0.64538(8) 0.5414(2) 0.0524(4) Uani d . 1 . .
H H5 -0.0509 0.6346 0.4346 0.063 Uiso calc R 1 . .
C C6 0.0777(2) 0.61027(7) 0.66396(19) 0.0455(4) Uani d . 1 . .
C C7 0.1590(2) 0.55591(7) 0.61664(19) 0.0485(4) Uani d . 1 . .
C C8 0.3333(2) 0.42967(7) 0.99547(18) 0.0432(4) Uani d . 1 . .
C C9 0.4310(2) 0.39466(8) 1.1233(2) 0.0527(4) Uani d . 1 . .
H H9 0.5048 0.3655 1.1072 0.063 Uiso calc R 1 . .
C C10 0.4182(3) 0.40325(8) 1.2745(2) 0.0572(5) Uani d . 1 . .
H H10 0.4845 0.3804 1.3609 0.069 Uiso calc R 1 . .
C C11 0.3068(2) 0.44583(8) 1.2965(2) 0.0533(4) Uani d . 1 . .
H H11 0.2958 0.4523 1.3971 0.064 Uiso calc R 1 . .
C C12 0.2125(2) 0.47854(8) 1.1649(2) 0.0551(4) Uani d . 1 . .
H H12 0.1363 0.5072 1.1789 0.066 Uiso calc R 1 . .
C C13 0.3515(2) 0.42534(7) 0.83260(18) 0.0433(4) Uani d . 1 . .
C C14 0.4492(2) 0.37362(7) 0.79543(18) 0.0444(4) Uani d . 1 . .
C C15 0.5690(2) 0.38299(8) 0.71803(19) 0.0514(4) Uani d . 1 . .
H H15 0.5880 0.4216 0.6856 0.062 Uiso calc R 1 . .
C C16 0.6594(2) 0.33445(9) 0.6899(2) 0.0611(5) Uani d . 1 . .
H H16 0.7415 0.3399 0.6399 0.073 Uiso calc R 1 . .
C C17 0.6260(3) 0.27757(9) 0.7371(2) 0.0645(5) Uani d . 1 . .
H H17 0.6853 0.2440 0.7199 0.077 Uiso calc R 1 . .
C C18 0.5033(3) 0.27192(8) 0.8099(2) 0.0617(5) Uani d . 1 . .
H H18 0.4802 0.2334 0.8399 0.074 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
C7 N1 N2 . . 120.17(13) ?
C7 N1 H7 . . 119.9 ?
N2 N1 H7 . . 119.9 ?
C2 C1 C6 . . 120.52(16) ?
C2 C1 H1 . . 119.7 ?
C6 C1 H1 . . 119.7 ?
C13 N2 N1 . . 118.27(12) ?
C3 C2 C1 . . 119.78(16) ?
C3 C2 H2 . . 120.1 ?
C1 C2 H2 . . 120.1 ?
C12 N3 C8 . . 118.61(14) ?
C4 C3 C2 . . 120.29(16) ?
C4 C3 H3 . . 119.9 ?
C2 C3 H3 . . 119.9 ?
C18 N4 C14 . . 116.92(15) ?
C3 C4 C5 . . 120.30(16) ?
C3 C4 H4 . . 119.8 ?
C5 C4 H4 . . 119.8 ?
C4 C5 C6 . . 120.28(16) ?
C4 C5 H5 . . 119.9 ?
C6 C5 H5 . . 119.9 ?
C1 C6 C5 . . 118.80(15) ?
C1 C6 C7 . . 123.43(14) ?
C5 C6 C7 . . 117.76(14) ?
O1 C7 N1 . . 124.24(15) ?
O1 C7 C6 . . 122.38(14) ?
N1 C7 C6 . . 113.37(13) ?
N3 C8 C9 . . 120.41(14) ?
N3 C8 C13 . . 117.62(13) ?
C9 C8 C13 . . 121.88(14) ?
C10 C9 C8 . . 119.78(15) ?
C10 C9 H9 . . 120.1 ?
C8 C9 H9 . . 120.1 ?
C11 C10 C9 . . 119.62(16) ?
C11 C10 H10 . . 120.2 ?
C9 C10 H10 . . 120.2 ?
C12 C11 C10 . . 117.75(15) ?
C12 C11 H11 . . 121.1 ?
C10 C11 H11 . . 121.1 ?
N3 C12 C11 . . 123.82(16) ?
N3 C12 H12 . . 118.1 ?
C11 C12 H12 . . 118.1 ?
N2 C13 C8 . . 127.81(14) ?
N2 C13 C14 . . 112.79(13) ?
C8 C13 C14 . . 119.29(13) ?
N4 C14 C15 . . 122.42(15) ?
N4 C14 C13 . . 116.60(14) ?
C15 C14 C13 . . 120.98(14) ?
C16 C15 C14 . . 119.18(16) ?
C16 C15 H15 . . 120.4 ?
C14 C15 H15 . . 120.4 ?
C15 C16 C17 . . 118.97(17) ?
C15 C16 H16 . . 120.5 ?
C17 C16 H16 . . 120.5 ?
C18 C17 C16 . . 118.30(17) ?
C18 C17 H17 . . 120.8 ?
C16 C17 H17 . . 120.9 ?
N4 C18 C17 . . 124.18(17) ?
N4 C18 H18 . . 117.9 ?
C17 C18 H18 . . 117.9 ?
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 C7 . 1.2217(18) ?
N1 C7 . 1.365(2) ?
N1 N2 . 1.3677(17) ?
N1 H7 . 0.8600 ?
C1 C2 . 1.386(2) ?
C1 C6 . 1.392(2) ?
C1 H1 . 0.9300 ?
N2 C13 . 1.302(2) ?
C2 C3 . 1.384(3) ?
C2 H2 . 0.9300 ?
N3 C12 . 1.338(2) ?
N3 C8 . 1.355(2) ?
C3 C4 . 1.371(3) ?
C3 H3 . 0.9300 ?
N4 C18 . 1.343(2) ?
N4 C14 . 1.3458(19) ?
C4 C5 . 1.385(2) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.394(2) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.502(2) ?
C8 C9 . 1.389(2) ?
C8 C13 . 1.492(2) ?
C9 C10 . 1.382(2) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.375(2) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.374(2) ?
C11 H11 . 0.9300 ?
C12 H12 . 0.9300 ?
C13 C14 . 1.498(2) ?
C14 C15 . 1.389(2) ?
C15 C16 . 1.377(2) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.382(3) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.371(3) ?
C17 H17 . 0.9300 ?
C18 H18 . 0.9300 ?
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
N1 H7 N3 . 0.86 1.94 2.624(2) 135.7 y
C9 H9 N4 . 0.93 2.45 2.973(2) 115 y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 599759
