#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/04/2210467.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_2210467
loop_
_publ_author_name
'Fang-Fang Jian'
'Tong-Ling liang'
'Ying-Qi Qin'
'Huan-Qing Yu'
'Hai-Lian Xiao'
_publ_section_title
;
 2'-(4-Methylbenzylidene)-5-phenyl-1H-pyrazole-3-carbohydrazide
;
_journal_coeditor_code           AT2100
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4364
_journal_page_last               o4365
_journal_paper_doi               10.1107/S1600536806035525
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C18 H16 N4 O'
_chemical_formula_moiety         'C18 H16 N4 O'
_chemical_formula_sum            'C18 H16 N4 O'
_chemical_formula_weight         304.35
_chemical_name_systematic
;
2'-(4-Methylbenzylidene)-5-phenyl-1H-pyrazole-3-carbohydrazide
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 106.27(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.280(4)
_cell_length_b                   14.790(3)
_cell_length_c                   13.364(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      14
_cell_measurement_theta_min      4
_cell_volume                     3468.4(14)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'NRCVAX (Gabe et al.,  1989)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material
'PARST (Nardelli, 1996) and WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_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  0.0433
_diffrn_reflns_av_sigmaI/netI    0.0472
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6290
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         1.80
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.234
_refine_ls_extinction_coef       0.0061(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3053
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1054
_refine_ls_R_factor_gt           0.0505
_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)+(0.0905P)²+0.2393P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1652
_reflns_number_gt                1730
_reflns_number_total             3053
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2100.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2210467
_cod_database_fobs_code          2210467
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
O O1 0.13587(9) -0.02743(12) 1.03240(11) 0.0759(6) Uani d . 1
N N1 0.11346(10) 0.09382(13) 0.71886(13) 0.0586(5) Uani d . 1
H H1A 0.1075 0.0977 0.6528 0.070 Uiso calc R 1
N N2 0.08569(10) 0.02553(12) 0.76346(12) 0.0553(5) Uani d . 1
N N3 0.02981(11) -0.07092(13) 0.90673(13) 0.0610(5) Uani d . 1
H H3A -0.0027 -0.0579 0.8483 0.073 Uiso calc R 1
N N4 0.01842(11) -0.14562(13) 0.96415(14) 0.0625(5) Uani d . 1
C C1 0.20332(17) 0.31043(18) 0.8226(2) 0.0867(9) Uani d . 1
H H1B 0.1891 0.3105 0.8842 0.104 Uiso calc R 1
C C2 0.2393(2) 0.3854(2) 0.7959(3) 0.1095(11) Uani d . 1
H H2B 0.2498 0.4354 0.8398 0.131 Uiso calc R 1
C C3 0.2594(2) 0.3855(3) 0.7036(3) 0.1207(13) Uani d . 1
H H3B 0.2830 0.4361 0.6852 0.145 Uiso calc R 1
C C4 0.2452(2) 0.3124(3) 0.6394(3) 0.1267(14) Uani d . 1
H H4B 0.2595 0.3133 0.5778 0.152 Uiso calc R 1
C C5 0.20983(17) 0.2369(2) 0.6647(2) 0.0949(9) Uani d . 1
H H5A 0.2002 0.1872 0.6203 0.114 Uiso calc R 1
C C6 0.18836(13) 0.23517(16) 0.75774(17) 0.0637(7) Uani d . 1
C C7 0.15189(12) 0.15604(16) 0.78853(16) 0.0573(6) Uani d . 1
C C8 0.14850(13) 0.12514(16) 0.88628(16) 0.0612(7) Uani d . 1
H H8A 0.1695 0.1525 0.9506 0.073 Uiso calc R 1
C C9 0.10742(12) 0.04546(15) 0.86692(15) 0.0531(6) Uani d . 1
C C10 0.09184(13) -0.01969(16) 0.94359(15) 0.0564(6) Uani d . 1
C C11 -0.03923(15) -0.19390(17) 0.92147(19) 0.0697(7) Uani d . 1
H H11A -0.0727 -0.1746 0.8591 0.084 Uiso calc R 1
C C12 -0.05454(14) -0.27881(17) 0.96745(19) 0.0696(7) Uani d . 1
C C13 -0.00759(18) -0.3115(2) 1.0615(2) 0.0924(9) Uani d . 1
H H13A 0.0332 -0.2766 1.0991 0.111 Uiso calc R 1
C C14 -0.0207(2) -0.3947(2) 1.0996(2) 0.1025(10) Uani d . 1
H H14A 0.0126 -0.4152 1.1615 0.123 Uiso calc R 1
C C15 -0.0810(2) -0.4481(2) 1.0496(3) 0.1000(10) Uani d . 1
C C16 -0.1279(2) -0.4153(2) 0.9567(3) 0.1115(11) Uani d . 1
H H16A -0.1694 -0.4499 0.9205 0.134 Uiso calc R 1
C C17 -0.11505(17) -0.3321(2) 0.9155(3) 0.0980(10) Uani d . 1
H H17A -0.1475 -0.3124 0.8525 0.118 Uiso calc R 1
C C18 -0.0964(3) -0.5390(2) 1.0922(3) 0.1471(16) Uani d . 1
H H18A -0.1275 -0.5750 1.0366 0.221 Uiso calc R 1
H H18B -0.1225 -0.5300 1.1445 0.221 Uiso calc R 1
H H18C -0.0490 -0.5694 1.1223 0.221 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
_geom_angle_publ_flag
N2 N1 C7 113.14(16) ?
N2 N1 H1A 123.4 ?
C7 N1 H1A 123.4 ?
N1 N2 C9 104.44(17) yes
C10 N3 N4 119.22(17) ?
C10 N3 H3A 120.4 yes
N4 N3 H3A 120.4 ?
C11 N4 N3 115.60(19) yes
C2 C1 C6 120.3(3) ?
C2 C1 H1B 119.8 ?
C6 C1 H1B 119.8 ?
C3 C2 C1 119.6(3) ?
C3 C2 H2B 120.2 ?
C1 C2 H2B 120.2 ?
C4 C3 C2 120.7(3) ?
C4 C3 H3B 119.6 ?
C2 C3 H3B 119.6 ?
C3 C4 C5 120.6(3) ?
C3 C4 H4B 119.7 ?
C5 C4 H4B 119.7 ?
C4 C5 C6 119.9(3) ?
C4 C5 H5A 120.0 ?
C6 C5 H5A 120.0 ?
C1 C6 C5 118.8(3) ?
C1 C6 C7 119.4(2) ?
C5 C6 C7 121.8(2) ?
N1 C7 C8 105.6(2) ?
N1 C7 C6 122.62(19) ?
C8 C7 C6 131.8(2) ?
C9 C8 C7 105.49(19) ?
C9 C8 H8A 127.3 ?
C7 C8 H8A 127.3 ?
N2 C9 C8 111.33(19) ?
N2 C9 C10 120.08(19) ?
C8 C9 C10 128.37(18) ?
O1 C10 N3 123.8(2) yes
O1 C10 C9 121.4(2) ?
N3 C10 C9 114.73(17) ?
N4 C11 C12 121.9(2) ?
N4 C11 H11A 119.1 ?
C12 C11 H11A 119.1 ?
C17 C12 C13 117.4(3) ?
C17 C12 C11 120.1(3) ?
C13 C12 C11 122.4(2) ?
C14 C13 C12 121.1(3) ?
C14 C13 H13A 119.5 ?
C12 C13 H13A 119.5 ?
C15 C14 C13 122.3(3) ?
C15 C14 H14A 118.8 ?
C13 C14 H14A 118.8 ?
C14 C15 C16 116.6(3) ?
C14 C15 C18 122.5(4) ?
C16 C15 C18 120.9(4) ?
C15 C16 C17 122.2(3) ?
C15 C16 H16A 118.9 ?
C17 C16 H16A 118.9 ?
C12 C17 C16 120.4(3) ?
C12 C17 H17A 119.8 ?
C16 C17 H17A 119.8 ?
C15 C18 H18A 109.5 ?
C15 C18 H18B 109.5 ?
H18A C18 H18B 109.5 ?
C15 C18 H18C 109.5 ?
H18A C18 H18C 109.5 ?
H18B C18 H18C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C10 1.239(2) yes
N1 N2 1.343(2) yes
N1 C7 1.357(3) ?
N1 H1A 0.8600 ?
N2 C9 1.360(2) ?
N3 C10 1.338(3) ?
N3 N4 1.394(2) ?
N3 H3A 0.8600 ?
N4 C11 1.269(3) yes
C1 C2 1.386(4) ?
C1 C6 1.390(3) ?
C1 H1B 0.9300 ?
C2 C3 1.383(5) ?
C2 H2B 0.9300 ?
C3 C4 1.360(5) ?
C3 H3B 0.9300 ?
C4 C5 1.379(4) ?
C4 H4B 0.9300 ?
C5 C6 1.404(4) ?
C5 H5A 0.9300 ?
C6 C7 1.462(3) yes
C7 C8 1.402(3) ?
C8 C9 1.382(3) ?
C8 H8A 0.9300 ?
C9 C10 1.491(3) ?
C11 C12 1.459(3) ?
C11 H11A 0.9300 ?
C12 C17 1.377(4) ?
C12 C13 1.395(3) ?
C13 C14 1.377(4) ?
C13 H13A 0.9300 ?
C14 C15 1.369(4) ?
C14 H14A 0.9300 ?
C15 C16 1.384(4) ?
C15 C18 1.516(4) ?
C16 C17 1.395(4) ?
C16 H16A 0.9300 ?
C17 H17A 0.9300 ?
C18 H18A 0.9600 ?
C18 H18B 0.9600 ?
C18 H18C 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
N1 H1A O1 6 0.86 2.10 2.813(2) 140.0
N3 H3A N2 2_556 0.86 2.19 2.996(3) 156.4
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 N1 N2 C9 0.2(2)
C10 N3 N4 C11 -176.1(2)
C6 C1 C2 C3 0.8(5)
C1 C2 C3 C4 -0.9(6)
C2 C3 C4 C5 0.5(6)
C3 C4 C5 C6 -0.2(5)
C2 C1 C6 C5 -0.4(4)
C2 C1 C6 C7 178.7(2)
C4 C5 C6 C1 0.1(4)
C4 C5 C6 C7 -179.0(3)
N2 N1 C7 C8 0.0(3)
N2 N1 C7 C6 178.7(2)
C1 C6 C7 N1 157.9(2)
C5 C6 C7 N1 -23.0(4)
C1 C6 C7 C8 -23.7(4)
C5 C6 C7 C8 155.4(3)
N1 C7 C8 C9 -0.1(2)
C6 C7 C8 C9 -178.7(2)
N1 N2 C9 C8 -0.2(2)
N1 N2 C9 C10 -175.20(18)
C7 C8 C9 N2 0.2(3)
C7 C8 C9 C10 174.7(2)
N4 N3 C10 O1 -9.3(3)
N4 N3 C10 C9 167.28(18)
N2 C9 C10 O1 147.0(2)
C8 C9 C10 O1 -27.0(4)
N2 C9 C10 N3 -29.7(3)
C8 C9 C10 N3 156.3(2)
N3 N4 C11 C12 174.1(2)
N4 C11 C12 C17 -175.9(3)
N4 C11 C12 C13 0.9(4)
C17 C12 C13 C14 1.2(5)
C11 C12 C13 C14 -175.7(3)
C12 C13 C14 C15 -1.9(5)
C13 C14 C15 C16 1.3(5)
C13 C14 C15 C18 -178.9(3)
C14 C15 C16 C17 -0.1(6)
C18 C15 C16 C17 -179.9(3)
C13 C12 C17 C16 0.0(5)
C11 C12 C17 C16 177.0(3)
C15 C16 C17 C12 -0.6(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 5260851
