#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/78/2207885.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_2207885
loop_
_publ_author_name
'Chen, Shui-Sheng'
'Zhang, Shu-Ping'
'Huang, Cong-Bao'
'Shao, Si-Chang'
_publ_section_title
;
 1-(4-Aminophenyl)ethanone isonicotinoylhydrazone
;
_journal_coeditor_code           SJ6169
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o31
_journal_page_last               o32
_journal_paper_doi               10.1107/S1600536805039516
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C14 H14 N4 O'
_chemical_formula_moiety         'C14 H14 N4 O'
_chemical_formula_sum            'C14 H14 N4 O'
_chemical_formula_weight         254.29
_chemical_name_systematic
;
1-(4-Aminophenyl)ethanone isonicotinoylhydrazone
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.000(3)
_cell_angle_beta                 95.415(3)
_cell_angle_gamma                90.000(3)
_cell_formula_units_Z            4
_cell_length_a                   7.9137(15)
_cell_length_b                   5.3466(10)
_cell_length_c                   29.650(6)
_cell_measurement_reflns_used    1324
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      53.925
_cell_measurement_theta_min      5.224
_cell_volume                     1248.9(4)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 2000)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_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 APEX area-detector'
_diffrn_measurement_method       'φ and 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  0.0427
_diffrn_reflns_av_sigmaI/netI    0.0452
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            5756
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.38
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.9822
_exptl_absorpt_correction_T_min  0.9735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.229
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.328
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2193
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.328
_refine_ls_R_factor_all          0.1131
_refine_ls_R_factor_gt           0.1003
_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)+(0.034P)²+1.5639P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1779
_refine_ls_wR_factor_ref         0.1833
_reflns_number_gt                1936
_reflns_number_total             2193
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj6169.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_sg_symbol_H-M      'P 21/n'
_cod_database_code               2207885
_cod_database_fobs_code          2207885
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_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_type_symbol
O1 0.7070(5) 0.6729(6) -0.00750(10) 0.0637(10) Uani d 1 O
N1 0.9652(7) 0.6134(9) 0.26696(13) 0.0618(13) Uani d 1 N
H1A 1.021(6) 0.529(9) 0.2871(16) 0.058(15) Uiso d 1 H
H1B 0.896(6) 0.729(9) 0.2747(15) 0.055(15) Uiso d 1 H
N2 0.7709(4) 0.3526(6) 0.06240(10) 0.0423(9) Uani d 1 N
N3 0.7454(5) 0.2766(7) 0.01766(11) 0.0419(9) Uani d 1 N
H3A 0.749(4) 0.124(7) 0.0101(12) 0.025(10) Uiso d 1 H
N4 0.6067(5) 0.1699(7) -0.14986(11) 0.0475(9) Uani d 1 N
C1 0.8754(5) 0.2929(7) 0.13793(12) 0.0360(9) Uani d 1 C
C2 0.7838(6) 0.4994(8) 0.15080(14) 0.0448(11) Uani d 1 C
H2 0.705(4) 0.572(6) 0.1293(12) 0.029(10) Uiso d 1 H
C3 0.8106(6) 0.6030(8) 0.19332(14) 0.0473(11) Uani d 1 C
H3 0.742(5) 0.748(8) 0.1996(13) 0.044(11) Uiso d 1 H
C4 0.9308(6) 0.5017(8) 0.22575(13) 0.0431(11) Uani d 1 C
C5 1.0166(6) 0.2902(9) 0.21401(14) 0.0492(12) Uani d 1 C
H5 1.089(5) 0.217(7) 0.2360(14) 0.043(11) Uiso d 1 H
C6 0.9887(6) 0.1890(8) 0.17131(14) 0.0432(11) Uani d 1 C
H6 1.059(5) 0.058(8) 0.1648(13) 0.045(12) Uiso d 1 H
C7 0.8539(5) 0.2061(7) 0.09040(12) 0.0331(9) Uani d 1 C
C8 0.9342(8) -0.0317(11) 0.07727(19) 0.0563(14) Uani d 1 C
H8A 0.856(6) -0.137(9) 0.0653(17) 0.070(17) Uiso d 1 H
H8B 1.010(6) 0.002(9) 0.0545(17) 0.072(16) Uiso d 1 H
H8C 1.004(7) -0.101(10) 0.1000(18) 0.087(19) Uiso d 1 H
C9 0.7076(5) 0.4484(8) -0.01463(13) 0.0388(10) Uani d 1 C
C10 0.6681(5) 0.3456(7) -0.06160(12) 0.0354(9) Uani d 1 C
C11 0.7245(6) 0.4743(8) -0.09750(14) 0.0446(11) Uani d 1 C
H11 0.791(5) 0.622(8) -0.0937(13) 0.045(12) Uiso d 1 H
C12 0.6912(6) 0.3807(9) -0.14050(14) 0.0513(12) Uani d 1 C
H12 0.735(5) 0.468(7) -0.1673(13) 0.043(11) Uiso d 1 H
C13 0.5499(6) 0.0522(9) -0.11515(15) 0.0451(11) Uani d 1 C
H13 0.484(5) -0.089(7) -0.1217(12) 0.031(10) Uiso d 1 H
C14 0.5767(6) 0.1298(8) -0.07084(14) 0.0410(10) Uani d 1 C
H14 0.537(5) 0.047(7) -0.0481(13) 0.042(12) Uiso d 1 H
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
C4 N1 H1A 117(3)
C4 N1 H1B 118(3)
H1A N1 H1B 120(4)
C7 N2 N3 117.5(3)
C9 N3 N2 119.1(3)
C9 N3 H3A 119(2)
N2 N3 H3A 122(2)
C13 N4 C12 116.3(4)
C6 C1 C2 116.1(4)
C6 C1 C7 124.2(4)
C2 C1 C7 119.6(4)
C3 C2 C1 122.1(4)
C3 C2 H2 120(2)
C1 C2 H2 118(2)
C2 C3 C4 120.7(4)
C2 C3 H3 117(2)
C4 C3 H3 122(2)
N1 C4 C5 121.5(4)
N1 C4 C3 120.8(4)
C5 C4 C3 117.6(4)
C6 C5 C4 120.9(4)
C6 C5 H5 122(3)
C4 C5 H5 117(3)
C5 C6 C1 122.4(4)
C5 C6 H6 116(3)
C1 C6 H6 121(2)
N2 C7 C1 115.6(3)
N2 C7 C8 124.0(4)
C1 C7 C8 120.2(4)
C7 C8 H8A 110(3)
C7 C8 H8B 110(3)
H8A C8 H8B 107(4)
C7 C8 H8C 113(3)
H8A C8 H8C 113(5)
H8B C8 H8C 103(4)
O1 C9 N3 123.8(4)
O1 C9 C10 121.1(4)
N3 C9 C10 115.1(3)
C14 C10 C11 117.9(4)
C14 C10 C9 123.4(4)
C11 C10 C9 118.6(4)
C12 C11 C10 119.2(4)
C12 C11 H11 118(2)
C10 C11 H11 123(2)
N4 C12 C11 123.6(4)
N4 C12 H12 115(2)
C11 C12 H12 121(2)
N4 C13 C14 124.6(4)
N4 C13 H13 117(2)
C14 C13 H13 118(2)
C13 C14 C10 118.3(4)
C13 C14 H14 123(3)
C10 C14 H14 119(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C9 1.219(5)
N1 C4 1.364(5)
N1 H1A 0.84(5)
N1 H1B 0.87(5)
N2 C7 1.277(5)
N2 N3 1.384(4)
N3 C9 1.340(5)
N3 H3A 0.85(4)
N4 C13 1.321(5)
N4 C12 1.326(6)
C1 C6 1.387(5)
C1 C2 1.393(6)
C1 C7 1.478(5)
C2 C3 1.375(6)
C2 H2 0.93(4)
C3 C4 1.397(6)
C3 H3 0.97(4)
C4 C5 1.381(6)
C5 C6 1.375(6)
C5 H5 0.91(4)
C6 H6 0.92(4)
C7 C8 1.489(6)
C8 H8A 0.89(5)
C8 H8B 0.96(5)
C8 H8C 0.91(6)
C9 C10 1.503(5)
C10 C14 1.375(5)
C10 C11 1.377(5)
C11 C12 1.372(6)
C11 H11 0.95(4)
C12 H12 1.01(4)
C13 C14 1.375(6)
C13 H13 0.93(4)
C14 H14 0.89(4)
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
N1 H1A N4 4_666 0.84(5) 2.20(5) 3.018(6) 164(4)
N3 H3A O1 1_545 0.85(4) 2.48(4) 3.320(5) 169(3)
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
C7 N2 N3 C9 -159.7(4)
C6 C1 C2 C3 3.5(6)
C7 C1 C2 C3 -173.6(4)
C1 C2 C3 C4 -0.8(7)
C2 C3 C4 N1 175.8(4)
C2 C3 C4 C5 -2.2(7)
N1 C4 C5 C6 -175.7(4)
C3 C4 C5 C6 2.3(7)
C4 C5 C6 C1 0.5(7)
C2 C1 C6 C5 -3.4(6)
C7 C1 C6 C5 173.6(4)
N3 N2 C7 C1 -179.0(3)
N3 N2 C7 C8 4.3(6)
C6 C1 C7 N2 -166.3(4)
C2 C1 C7 N2 10.6(5)
C6 C1 C7 C8 10.6(6)
C2 C1 C7 C8 -172.5(4)
N2 N3 C9 O1 6.0(7)
N2 N3 C9 C10 -175.2(3)
O1 C9 C10 C14 -142.3(4)
N3 C9 C10 C14 38.8(6)
O1 C9 C10 C11 37.0(6)
N3 C9 C10 C11 -141.8(4)
C14 C10 C11 C12 -1.5(6)
C9 C10 C11 C12 179.1(4)
C13 N4 C12 C11 1.7(7)
C10 C11 C12 N4 -0.1(7)
C12 N4 C13 C14 -1.9(6)
N4 C13 C14 C10 0.4(7)
C11 C10 C14 C13 1.3(6)
C9 C10 C14 C13 -179.3(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 7842866
