#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/64/2226402.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_2226402
loop_
_publ_author_name
'Asiri, Abdullah M.'
'Khan, Salman A.'
'Tan, Kong Wai'
'Ng, Seik Weng'
_publ_section_title
;
 4-[(3,4-Dimethoxybenzylidene)amino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one
;
_journal_coeditor_code           CV2733
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1732
_journal_paper_doi               10.1107/S1600536810023238
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C20 H21 N3 O3'
_chemical_formula_moiety         'C20 H21 N3 O3'
_chemical_formula_sum            'C20 H21 N3 O3'
_chemical_formula_weight         351.40
_chemical_name_systematic
;
4-[(3,4-Dimethoxybenzylidene)amino]-1,5-dimethyl-2-phenyl-
1H-pyrazol-3(2H)-one
;
_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                 109.0390(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.5584(8)
_cell_length_b                   10.4752(7)
_cell_length_c                   14.6002(9)
_cell_measurement_reflns_used    6153
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.2
_cell_measurement_theta_min      2.4
_cell_volume                     1815.6(2)
_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  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16900
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.72
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.243
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         4164
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0373
_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)+(0.0548P)²+0.5659P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.1032
_reflns_number_gt                3442
_reflns_number_total             4164
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv2733.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226402
_cod_database_fobs_code          2226402
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 0.28425(6) 0.77513(8) 0.59527(6) 0.01980(19) Uani d . 1 . .
O O2 0.86240(7) 0.62990(8) 0.50221(6) 0.02147(19) Uani d . 1 . .
O O3 0.86452(8) 0.84966(8) 0.42541(7) 0.0292(2) Uani d . 1 . .
N N1 0.26678(8) 0.60441(9) 0.69085(7) 0.0185(2) Uani d . 1 . .
N N2 0.33485(8) 0.50111(9) 0.73701(7) 0.0190(2) Uani d . 1 . .
N N3 0.50498(8) 0.62594(9) 0.60372(7) 0.0187(2) Uani d . 1 . .
C C1 0.18777(9) 0.65675(11) 0.73138(8) 0.0189(2) Uani d . 1 . .
C C2 0.09077(9) 0.71284(11) 0.66951(9) 0.0204(2) Uani d . 1 . .
H H2 0.0778 0.7155 0.6017 0.025 Uiso calc R 1 . .
C C3 0.01286(10) 0.76508(12) 0.70792(9) 0.0235(3) Uani d . 1 . .
H H3 -0.0530 0.8052 0.6662 0.028 Uiso calc R 1 . .
C C4 0.03033(10) 0.75915(12) 0.80662(9) 0.0252(3) Uani d . 1 . .
H H4 -0.0240 0.7936 0.8323 0.030 Uiso calc R 1 . .
C C5 0.12751(11) 0.70267(13) 0.86781(9) 0.0258(3) Uani d . 1 . .
H H5 0.1394 0.6982 0.9354 0.031 Uiso calc R 1 . .
C C6 0.20713(10) 0.65278(12) 0.83089(9) 0.0230(3) Uani d . 1 . .
H H6 0.2745 0.6161 0.8731 0.028 Uiso calc R 1 . .
C C7 0.31965(9) 0.67280(11) 0.63587(8) 0.0171(2) Uani d . 1 . .
C C8 0.41934(9) 0.59911(11) 0.64197(8) 0.0173(2) Uani d . 1 . .
C C9 0.42229(9) 0.49573(11) 0.70009(8) 0.0179(2) Uani d . 1 . .
C C10 0.50361(10) 0.38826(12) 0.72347(9) 0.0231(3) Uani d . 1 . .
H H10A 0.5663 0.4077 0.6996 0.035 Uiso calc R 1 . .
H H10B 0.4657 0.3102 0.6924 0.035 Uiso calc R 1 . .
H H10C 0.5326 0.3759 0.7938 0.035 Uiso calc R 1 . .
C C11 0.27490(10) 0.38645(11) 0.75111(9) 0.0225(3) Uani d . 1 . .
H H11A 0.2343 0.4054 0.7965 0.034 Uiso calc R 1 . .
H H11B 0.3292 0.3177 0.7774 0.034 Uiso calc R 1 . .
H H11C 0.2212 0.3597 0.6888 0.034 Uiso calc R 1 . .
C C12 0.49724(9) 0.72136(11) 0.54678(8) 0.0191(2) Uani d . 1 . .
H H12 0.4304 0.7713 0.5274 0.023 Uiso calc R 1 . .
C C13 0.59014(9) 0.75419(11) 0.51128(8) 0.0187(2) Uani d . 1 . .
C C14 0.68242(9) 0.67130(11) 0.52633(8) 0.0182(2) Uani d . 1 . .
H H14 0.6838 0.5919 0.5582 0.022 Uiso calc R 1 . .
C C15 0.77102(9) 0.70504(11) 0.49495(8) 0.0186(2) Uani d . 1 . .
C C16 0.77122(10) 0.82494(11) 0.45064(9) 0.0213(2) Uani d . 1 . .
C C17 0.68007(11) 0.90626(12) 0.43516(9) 0.0241(3) Uani d . 1 . .
H H17 0.6794 0.9867 0.4049 0.029 Uiso calc R 1 . .
C C18 0.58924(10) 0.86946(11) 0.46420(9) 0.0222(3) Uani d . 1 . .
H H18 0.5257 0.9242 0.4515 0.027 Uiso calc R 1 . .
C C19 0.87115(10) 0.51317(11) 0.55464(9) 0.0229(3) Uani d . 1 . .
H H19A 0.9404 0.4687 0.5564 0.034 Uiso calc R 1 . .
H H19B 0.8060 0.4590 0.5226 0.034 Uiso calc R 1 . .
H H19C 0.8730 0.5316 0.6209 0.034 Uiso calc R 1 . .
C C20 0.86692(15) 0.96944(14) 0.37878(14) 0.0452(4) Uani d . 1 . .
H H20A 0.9381 0.9775 0.3652 0.068 Uiso calc R 1 . .
H H20B 0.8605 1.0393 0.4213 0.068 Uiso calc R 1 . .
H H20C 0.8038 0.9735 0.3179 0.068 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
C15 O2 C19 . . 116.78(9) ?
C16 O3 C20 . . 116.62(10) ?
C7 N1 N2 . . 109.98(9) ?
C7 N1 C1 . . 124.72(10) ?
N2 N1 C1 . . 119.67(9) ?
C9 N2 N1 . . 106.39(9) ?
C9 N2 C11 . . 122.28(10) ?
N1 N2 C11 . . 115.93(9) ?
C12 N3 C8 . . 120.78(10) ?
C2 C1 C6 . . 120.57(11) ?
C2 C1 N1 . . 118.44(10) ?
C6 C1 N1 . . 120.99(10) ?
C1 C2 C3 . . 119.23(11) ?
C1 C2 H2 . . 120.4 ?
C3 C2 H2 . . 120.4 ?
C4 C3 C2 . . 120.56(11) ?
C4 C3 H3 . . 119.7 ?
C2 C3 H3 . . 119.7 ?
C3 C4 C5 . . 119.73(11) ?
C3 C4 H4 . . 120.1 ?
C5 C4 H4 . . 120.1 ?
C6 C5 C4 . . 120.37(12) ?
C6 C5 H5 . . 119.8 ?
C4 C5 H5 . . 119.8 ?
C5 C6 C1 . . 119.50(11) ?
C5 C6 H6 . . 120.2 ?
C1 C6 H6 . . 120.2 ?
O1 C7 N1 . . 123.87(10) ?
O1 C7 C8 . . 131.33(10) ?
N1 C7 C8 . . 104.77(9) ?
C9 C8 N3 . . 122.68(10) ?
C9 C8 C7 . . 107.92(10) ?
N3 C8 C7 . . 129.26(10) ?
C8 C9 N2 . . 110.34(10) ?
C8 C9 C10 . . 128.36(11) ?
N2 C9 C10 . . 121.31(10) ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
N2 C11 H11A . . 109.5 ?
N2 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
N2 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
N3 C12 C13 . . 120.78(10) ?
N3 C12 H12 . . 119.6 ?
C13 C12 H12 . . 119.6 ?
C18 C13 C14 . . 119.19(11) ?
C18 C13 C12 . . 120.08(10) ?
C14 C13 C12 . . 120.71(10) ?
C15 C14 C13 . . 120.15(11) ?
C15 C14 H14 . . 119.9 ?
C13 C14 H14 . . 119.9 ?
O2 C15 C14 . . 125.03(10) ?
O2 C15 C16 . . 114.87(10) ?
C14 C15 C16 . . 120.10(10) ?
O3 C16 C17 . . 125.23(11) ?
O3 C16 C15 . . 115.00(10) ?
C17 C16 C15 . . 119.77(11) ?
C16 C17 C18 . . 119.66(11) ?
C16 C17 H17 . . 120.2 ?
C18 C17 H17 . . 120.2 ?
C13 C18 C17 . . 121.05(11) ?
C13 C18 H18 . . 119.5 ?
C17 C18 H18 . . 119.5 ?
O2 C19 H19A . . 109.5 ?
O2 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
O2 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
O3 C20 H20A . . 109.5 ?
O3 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
O3 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 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
O1 C7 . 1.2354(14) ?
O2 C15 . 1.3669(14) ?
O2 C19 . 1.4277(14) ?
O3 C16 . 1.3627(14) ?
O3 C20 . 1.4326(16) ?
N1 C7 . 1.3950(14) ?
N1 N2 . 1.4072(13) ?
N1 C1 . 1.4206(15) ?
N2 C9 . 1.3731(15) ?
N2 C11 . 1.4673(14) ?
N3 C12 . 1.2833(15) ?
N3 C8 . 1.3926(14) ?
C1 C2 . 1.3883(16) ?
C1 C6 . 1.3933(17) ?
C2 C3 . 1.3890(17) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.3865(18) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.3879(19) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.3839(18) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 C8 . 1.4486(15) ?
C8 C9 . 1.3688(16) ?
C9 C10 . 1.4830(16) ?
C10 H10A . 0.9800 ?
C10 H10B . 0.9800 ?
C10 H10C . 0.9800 ?
C11 H11A . 0.9800 ?
C11 H11B . 0.9800 ?
C11 H11C . 0.9800 ?
C12 C13 . 1.4638(16) ?
C12 H12 . 0.9500 ?
C13 C18 . 1.3876(17) ?
C13 C14 . 1.4067(16) ?
C14 C15 . 1.3804(16) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.4132(16) ?
C16 C17 . 1.3851(17) ?
C17 C18 . 1.3946(17) ?
C17 H17 . 0.9500 ?
C18 H18 . 0.9500 ?
C19 H19A . 0.9800 ?
C19 H19B . 0.9800 ?
C19 H19C . 0.9800 ?
C20 H20A . 0.9800 ?
C20 H20B . 0.9800 ?
C20 H20C . 0.9800 ?
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
C7 N1 N2 C9 . . . . -8.00(12) ?
C1 N1 N2 C9 . . . . -162.78(10) ?
C7 N1 N2 C11 . . . . -147.65(10) ?
C1 N1 N2 C11 . . . . 57.57(13) ?
C7 N1 C1 C2 . . . . 58.12(15) ?
N2 N1 C1 C2 . . . . -151.03(10) ?
C7 N1 C1 C6 . . . . -121.50(12) ?
N2 N1 C1 C6 . . . . 29.34(16) ?
C6 C1 C2 C3 . . . . -0.05(17) ?
N1 C1 C2 C3 . . . . -179.68(10) ?
C1 C2 C3 C4 . . . . -1.31(18) ?
C2 C3 C4 C5 . . . . 1.22(18) ?
C3 C4 C5 C6 . . . . 0.25(19) ?
C4 C5 C6 C1 . . . . -1.59(19) ?
C2 C1 C6 C5 . . . . 1.50(18) ?
N1 C1 C6 C5 . . . . -178.89(11) ?
N2 N1 C7 O1 . . . . -172.69(10) ?
C1 N1 C7 O1 . . . . -19.46(17) ?
N2 N1 C7 C8 . . . . 5.75(12) ?
C1 N1 C7 C8 . . . . 158.98(10) ?
C12 N3 C8 C9 . . . . 177.56(11) ?
C12 N3 C8 C7 . . . . -7.18(18) ?
O1 C7 C8 C9 . . . . 176.90(12) ?
N1 C7 C8 C9 . . . . -1.37(12) ?
O1 C7 C8 N3 . . . . 1.1(2) ?
N1 C7 C8 N3 . . . . -177.18(11) ?
N3 C8 C9 N2 . . . . 172.54(10) ?
C7 C8 C9 N2 . . . . -3.61(13) ?
N3 C8 C9 C10 . . . . -8.03(19) ?
C7 C8 C9 C10 . . . . 175.83(11) ?
N1 N2 C9 C8 . . . . 7.08(12) ?
C11 N2 C9 C8 . . . . 143.54(11) ?
N1 N2 C9 C10 . . . . -172.41(10) ?
C11 N2 C9 C10 . . . . -35.94(16) ?
C8 N3 C12 C13 . . . . 176.26(10) ?
N3 C12 C13 C18 . . . . -168.62(11) ?
N3 C12 C13 C14 . . . . 9.85(17) ?
C18 C13 C14 C15 . . . . 0.35(17) ?
C12 C13 C14 C15 . . . . -178.13(10) ?
C19 O2 C15 C14 . . . . -6.31(16) ?
C19 O2 C15 C16 . . . . 174.22(10) ?
C13 C14 C15 O2 . . . . -177.20(10) ?
C13 C14 C15 C16 . . . . 2.23(17) ?
C20 O3 C16 C17 . . . . -0.3(2) ?
C20 O3 C16 C15 . . . . 178.96(13) ?
O2 C15 C16 O3 . . . . -2.53(15) ?
C14 C15 C16 O3 . . . . 177.98(11) ?
O2 C15 C16 C17 . . . . 176.81(11) ?
C14 C15 C16 C17 . . . . -2.68(18) ?
O3 C16 C17 C18 . . . . 179.80(12) ?
C15 C16 C17 C18 . . . . 0.52(19) ?
C14 C13 C18 C17 . . . . -2.54(18) ?
C12 C13 C18 C17 . . . . 175.95(11) ?
C16 C17 C18 C13 . . . . 2.10(19) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 938676
