#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/65/2226572.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_2226572
loop_
_publ_author_name
'Asiri, Abdullah M.'
'Khan, Salman A.'
'Tan, Kong Wai'
'Ng, Seik Weng'
_publ_section_title
;
 4-{[4-(Dimethylamino)benzylidene]amino}-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one
;
_journal_coeditor_code           KP2268
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1751
_journal_paper_doi               10.1107/S1600536810023536
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C20 H22 N4 O'
_chemical_formula_moiety         'C20 H22 N4 O'
_chemical_formula_sum            'C20 H22 N4 O'
_chemical_formula_weight         334.42
_chemical_name_systematic
;
4-{[4-(Dimethylamino)benzylidene]amino}-1,5-dimethyl-2-phenyl-
1H-pyrazol-3(2H)-one
;
_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                 101.4260(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.7275(14)
_cell_length_b                   6.7552(6)
_cell_length_c                   29.387(2)
_cell_measurement_reflns_used    3746
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.2
_cell_measurement_theta_min      2.3
_cell_volume                     3449.4(5)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'X-Seed (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX diffractometer'
_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  0.0429
_diffrn_reflns_av_sigmaI/netI    0.0393
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            15916
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.41
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Irregular
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.217
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3959
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0411
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0456P)²+1.6458P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.1008
_reflns_number_gt                3146
_reflns_number_total             3959
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            kp2268.cif
_cod_data_source_block           I
_cod_original_cell_volume        3449.5(5)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2226572
_cod_database_fobs_code          2226572
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.44182(5) 0.85565(14) 0.62281(3) 0.0206(2) Uani d . 1 . .
N N1 0.88210(7) 0.91371(18) 0.54534(4) 0.0232(3) Uani d . 1 . .
N N2 0.58578(6) 0.58777(17) 0.61620(4) 0.0173(2) Uani d . 1 . .
N N3 0.45341(6) 0.41420(16) 0.68429(4) 0.0163(2) Uani d . 1 . .
N N4 0.41440(6) 0.58791(16) 0.66631(4) 0.0166(2) Uani d . 1 . .
C C1 0.81084(8) 0.8721(2) 0.55470(4) 0.0196(3) Uani d . 1 . .
C C2 0.79273(8) 0.6806(2) 0.56883(4) 0.0204(3) Uani d . 1 . .
H H2 0.8292 0.5767 0.5700 0.024 Uiso calc R 1 . .
C C3 0.72303(8) 0.6430(2) 0.58096(4) 0.0194(3) Uani d . 1 . .
H H3 0.7125 0.5130 0.5903 0.023 Uiso calc R 1 . .
C C4 0.66719(8) 0.7900(2) 0.57993(4) 0.0182(3) Uani d . 1 . .
C C5 0.68396(8) 0.9775(2) 0.56453(5) 0.0210(3) Uani d . 1 . .
H H5 0.6466 1.0795 0.5626 0.025 Uiso calc R 1 . .
C C6 0.75351(8) 1.0189(2) 0.55193(5) 0.0219(3) Uani d . 1 . .
H H6 0.7627 1.1477 0.5413 0.026 Uiso calc R 1 . .
C C7 0.93806(8) 0.7568(2) 0.54517(5) 0.0253(3) Uani d . 1 . .
H H7A 0.9402 0.6730 0.5726 0.038 Uiso calc R 1 . .
H H7B 0.9889 0.8150 0.5457 0.038 Uiso calc R 1 . .
H H7C 0.9229 0.6766 0.5171 0.038 Uiso calc R 1 . .
C C8 0.89519(9) 1.0978(2) 0.52251(5) 0.0267(3) Uani d . 1 . .
H H8A 0.8791 1.2096 0.5396 0.040 Uiso calc R 1 . .
H H8B 0.8653 1.0975 0.4907 0.040 Uiso calc R 1 . .
H H8C 0.9500 1.1105 0.5219 0.040 Uiso calc R 1 . .
C C9 0.59614(8) 0.7527(2) 0.59633(4) 0.0183(3) Uani d . 1 . .
H H9 0.5571 0.8510 0.5923 0.022 Uiso calc R 1 . .
C C10 0.45790(7) 0.68849(19) 0.63871(4) 0.0162(3) Uani d . 1 . .
C C11 0.52186(8) 0.55737(19) 0.63643(4) 0.0160(3) Uani d . 1 . .
C C12 0.51466(7) 0.39349(19) 0.66245(4) 0.0160(3) Uani d . 1 . .
C C13 0.56351(8) 0.2136(2) 0.66934(5) 0.0206(3) Uani d . 1 . .
H H13A 0.6052 0.2271 0.6521 0.031 Uiso calc R 1 . .
H H13B 0.5322 0.0975 0.6580 0.031 Uiso calc R 1 . .
H H13C 0.5854 0.1973 0.7025 0.031 Uiso calc R 1 . .
C C14 0.40306(8) 0.2478(2) 0.69032(5) 0.0208(3) Uani d . 1 . .
H H14A 0.4343 0.1376 0.7054 0.031 Uiso calc R 1 . .
H H14B 0.3744 0.2051 0.6599 0.031 Uiso calc R 1 . .
H H14C 0.3668 0.2897 0.7097 0.031 Uiso calc R 1 . .
C C16 0.36949(7) 0.68935(18) 0.69429(4) 0.0154(3) Uani d . 1 . .
C C17 0.39115(7) 0.68983(19) 0.74243(4) 0.0168(3) Uani d . 1 . .
H H17 0.4349 0.6172 0.7574 0.020 Uiso calc R 1 . .
C C18 0.34793(8) 0.79786(19) 0.76822(5) 0.0181(3) Uani d . 1 . .
H H18 0.3619 0.7977 0.8011 0.022 Uiso calc R 1 . .
C C19 0.28464(8) 0.90595(19) 0.74637(5) 0.0187(3) Uani d . 1 . .
H H19 0.2559 0.9817 0.7642 0.022 Uiso calc R 1 . .
C C20 0.26332(8) 0.9032(2) 0.69835(5) 0.0196(3) Uani d . 1 . .
H H20 0.2198 0.9770 0.6833 0.024 Uiso calc R 1 . .
C C21 0.30522(8) 0.7932(2) 0.67215(5) 0.0180(3) Uani d . 1 . .
H H21 0.2900 0.7890 0.6393 0.022 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C7 . . 120.48(12) ?
C1 N1 C8 . . 120.29(12) ?
C7 N1 C8 . . 116.83(12) ?
C9 N2 C11 . . 121.43(12) ?
C12 N3 N4 . . 106.50(10) ?
C12 N3 C14 . . 122.31(11) ?
N4 N3 C14 . . 114.67(10) ?
C10 N4 N3 . . 109.57(10) ?
C10 N4 C16 . . 122.30(11) ?
N3 N4 C16 . . 118.13(10) ?
N1 C1 C6 . . 121.69(13) ?
N1 C1 C2 . . 121.11(13) ?
C6 C1 C2 . . 117.18(12) ?
C3 C2 C1 . . 120.83(13) ?
C3 C2 H2 . . 119.6 ?
C1 C2 H2 . . 119.6 ?
C2 C3 C4 . . 122.11(13) ?
C2 C3 H3 . . 118.9 ?
C4 C3 H3 . . 118.9 ?
C5 C4 C3 . . 117.13(12) ?
C5 C4 C9 . . 121.16(12) ?
C3 C4 C9 . . 121.64(12) ?
C6 C5 C4 . . 121.84(13) ?
C6 C5 H5 . . 119.1 ?
C4 C5 H5 . . 119.1 ?
C5 C6 C1 . . 120.84(13) ?
C5 C6 H6 . . 119.6 ?
C1 C6 H6 . . 119.6 ?
N1 C7 H7A . . 109.5 ?
N1 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
N1 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
N1 C8 H8A . . 109.5 ?
N1 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
N1 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
N2 C9 C4 . . 120.66(13) ?
N2 C9 H9 . . 119.7 ?
C4 C9 H9 . . 119.7 ?
O1 C10 N4 . . 123.44(12) ?
O1 C10 C11 . . 131.70(12) ?
N4 C10 C11 . . 104.81(11) ?
C12 C11 N2 . . 122.13(12) ?
C12 C11 C10 . . 107.96(11) ?
N2 C11 C10 . . 129.65(12) ?
C11 C12 N3 . . 110.45(11) ?
C11 C12 C13 . . 128.60(12) ?
N3 C12 C13 . . 120.93(12) ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
N3 C14 H14A . . 109.5 ?
N3 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
N3 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C21 C16 C17 . . 120.82(12) ?
C21 C16 N4 . . 118.22(11) ?
C17 C16 N4 . . 120.92(12) ?
C18 C17 C16 . . 119.08(12) ?
C18 C17 H17 . . 120.5 ?
C16 C17 H17 . . 120.5 ?
C19 C18 C17 . . 120.55(12) ?
C19 C18 H18 . . 119.7 ?
C17 C18 H18 . . 119.7 ?
C18 C19 C20 . . 119.82(12) ?
C18 C19 H19 . . 120.1 ?
C20 C19 H19 . . 120.1 ?
C19 C20 C21 . . 120.27(13) ?
C19 C20 H20 . . 119.9 ?
C21 C20 H20 . . 119.9 ?
C16 C21 C20 . . 119.44(12) ?
C16 C21 H21 . . 120.3 ?
C20 C21 H21 . . 120.3 ?
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 C10 . 1.2337(16) ?
N1 C1 . 1.3743(18) ?
N1 C7 . 1.4523(19) ?
N1 C8 . 1.4533(19) ?
N2 C9 . 1.2877(17) ?
N2 C11 . 1.3950(17) ?
N3 C12 . 1.3735(17) ?
N3 N4 . 1.4106(15) ?
N3 C14 . 1.4676(17) ?
N4 C10 . 1.4007(16) ?
N4 C16 . 1.4279(16) ?
C1 C6 . 1.410(2) ?
C1 C2 . 1.415(2) ?
C2 C3 . 1.3758(19) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.3982(19) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.3969(19) ?
C4 C9 . 1.4569(19) ?
C5 C6 . 1.3842(19) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 H7A . 0.9800 ?
C7 H7B . 0.9800 ?
C7 H7C . 0.9800 ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
C9 H9 . 0.9500 ?
C10 C11 . 1.4509(18) ?
C11 C12 . 1.3657(18) ?
C12 C13 . 1.4825(18) ?
C13 H13A . 0.9800 ?
C13 H13B . 0.9800 ?
C13 H13C . 0.9800 ?
C14 H14A . 0.9800 ?
C14 H14B . 0.9800 ?
C14 H14C . 0.9800 ?
C16 C21 . 1.3855(18) ?
C16 C17 . 1.3905(18) ?
C17 C18 . 1.3872(18) ?
C17 H17 . 0.9500 ?
C18 C19 . 1.3853(19) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.3867(19) ?
C19 H19 . 0.9500 ?
C20 C21 . 1.3871(19) ?
C20 H20 . 0.9500 ?
C21 H21 . 0.9500 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C12 N3 N4 C10 . . . . -8.61(13) ?
C14 N3 N4 C10 . . . . -147.15(11) ?
C12 N3 N4 C16 . . . . -155.05(11) ?
C14 N3 N4 C16 . . . . 66.41(14) ?
C7 N1 C1 C6 . . . . -175.50(12) ?
C8 N1 C1 C6 . . . . -13.63(19) ?
C7 N1 C1 C2 . . . . 6.28(19) ?
C8 N1 C1 C2 . . . . 168.15(13) ?
N1 C1 C2 C3 . . . . 175.89(12) ?
C6 C1 C2 C3 . . . . -2.41(19) ?
C1 C2 C3 C4 . . . . 0.1(2) ?
C2 C3 C4 C5 . . . . 1.99(19) ?
C2 C3 C4 C9 . . . . -175.04(12) ?
C3 C4 C5 C6 . . . . -1.7(2) ?
C9 C4 C5 C6 . . . . 175.37(12) ?
C4 C5 C6 C1 . . . . -0.7(2) ?
N1 C1 C6 C5 . . . . -175.58(12) ?
C2 C1 C6 C5 . . . . 2.7(2) ?
C11 N2 C9 C4 . . . . 173.20(12) ?
C5 C4 C9 N2 . . . . -170.60(12) ?
C3 C4 C9 N2 . . . . 6.3(2) ?
N3 N4 C10 O1 . . . . -171.71(12) ?
C16 N4 C10 O1 . . . . -26.94(19) ?
N3 N4 C10 C11 . . . . 5.99(13) ?
C16 N4 C10 C11 . . . . 150.76(11) ?
C9 N2 C11 C12 . . . . -171.88(12) ?
C9 N2 C11 C10 . . . . 1.4(2) ?
O1 C10 C11 C12 . . . . 176.26(14) ?
N4 C10 C11 C12 . . . . -1.17(14) ?
O1 C10 C11 N2 . . . . 2.2(2) ?
N4 C10 C11 N2 . . . . -175.21(12) ?
N2 C11 C12 N3 . . . . 170.36(11) ?
C10 C11 C12 N3 . . . . -4.23(15) ?
N2 C11 C12 C13 . . . . -8.4(2) ?
C10 C11 C12 C13 . . . . 177.05(12) ?
N4 N3 C12 C11 . . . . 7.87(14) ?
C14 N3 C12 C11 . . . . 142.49(12) ?
N4 N3 C12 C13 . . . . -173.29(11) ?
C14 N3 C12 C13 . . . . -38.67(18) ?
C10 N4 C16 C21 . . . . 68.38(16) ?
N3 N4 C16 C21 . . . . -149.66(12) ?
C10 N4 C16 C17 . . . . -109.37(14) ?
N3 N4 C16 C17 . . . . 32.58(17) ?
C21 C16 C17 C18 . . . . -0.70(19) ?
N4 C16 C17 C18 . . . . 177.00(11) ?
C16 C17 C18 C19 . . . . -0.84(19) ?
C17 C18 C19 C20 . . . . 1.3(2) ?
C18 C19 C20 C21 . . . . -0.2(2) ?
C17 C16 C21 C20 . . . . 1.8(2) ?
N4 C16 C21 C20 . . . . -175.97(12) ?
C19 C20 C21 C16 . . . . -1.3(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 474433
