#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/54/2235465.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_2235465
loop_
_publ_author_name
'Chaudhry, Faryal'
'Tahir, M. Nawaz'
'Khan, Misbahul Ain'
'Ather, Abdul Qayyum'
'Asif, Nadia'
_publ_section_title
;
 (4Z)-4-[(2E)-1-Hydroxy-3-(3-nitrophenyl)prop-2-en-1-ylidene]-3-methyl-1-(4-methylphenyl)-1H-pyrazol-5(4H)-one
;
_journal_coeditor_code           HB6835
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2044
_journal_paper_doi               10.1107/S1600536812025238
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C20 H17 N3 O4'
_chemical_formula_moiety         'C20 H17 N3 O4'
_chemical_formula_sum            'C20 H17 N3 O4'
_chemical_formula_weight         363.37
_chemical_name_systematic
;
(4Z)-4-[(2E)-1-Hydroxy-3-(3-nitrophenyl)prop-2-en-1-ylidene]-
3-methyl-1-(4-methylphenyl)-1H-pyrazol-5(4H)-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
_cell_angle_beta                 121.188(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   19.8712(16)
_cell_length_b                   12.1917(10)
_cell_length_c                   16.733(2)
_cell_measurement_reflns_used    1823
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      2.06
_cell_volume                     3467.9(6)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.00
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_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  0.0392
_diffrn_reflns_av_sigmaI/netI    0.0557
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12231
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.06
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.216
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3328
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1160
_refine_ls_R_factor_gt           0.0522
_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)+(0.0688P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1160
_refine_ls_wR_factor_ref         0.1426
_reflns_number_gt                1823
_reflns_number_total             3328
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb6835.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2235465
_cod_database_fobs_code          2235465
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,y,1/2-z
3 -x,-y,-z
4 x,-y,1/2+z
5 1/2+x,1/2+y,z
6 1/2-x,1/2+y,1/2-z
7 1/2-x,1/2-y,-z
8 1/2+x,1/2-y,1/2+z
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_thermal_displace_type
_atom_site_occupancy
_atom_site_disorder_group
O O1 -0.08035(9) 0.17748(13) 0.26833(13) 0.0730(6) Uani 1.000 -16
O O2 0.04784(9) 0.17674(14) 0.42872(13) 0.0821(7) Uani 1.000 -16
O O3 0.36766(10) 0.22769(14) 0.89614(12) 0.0776(7) Uani 1.000 -16
O O4 0.45928(10) 0.10845(15) 0.95844(14) 0.0945(8) Uani 1.000 -16
N N1 -0.12499(10) -0.00138(14) 0.21735(13) 0.0471(6) Uani 1.000 -16
N N2 -0.09808(10) -0.10774(14) 0.24985(14) 0.0569(7) Uani 1.000 -16
N N3 0.39439(11) 0.13844(17) 0.89657(14) 0.0581(8) Uani 1.000 -16
C C1 -0.19601(12) 0.01116(18) 0.12989(15) 0.0455(8) Uani 1.000 -16
C C2 -0.23410(13) -0.0800(2) 0.07708(16) 0.0553(8) Uani 1.000 -16
C C3 -0.30350(13) -0.0687(2) -0.00721(17) 0.0605(9) Uani 1.000 -16
C C4 -0.33702(12) 0.0320(2) -0.04231(17) 0.0580(9) Uani 1.000 -16
C C5 -0.29776(13) 0.1220(2) 0.01114(18) 0.0625(9) Uani 1.000 -16
C C6 -0.22799(13) 0.11356(19) 0.09640(17) 0.0570(9) Uani 1.000 -16
C C7 -0.41344(14) 0.0434(3) -0.13425(18) 0.0807(10) Uani 1.000 -16
C C8 -0.03201(13) -0.09808(19) 0.32890(17) 0.0529(8) Uani 1.000 -16
C C9 0.01174(15) -0.19835(19) 0.3795(2) 0.0829(10) Uani 1.000 -16
C C10 -0.01225(12) 0.01440(18) 0.35383(16) 0.0470(7) Uani 1.000 -16
C C11 -0.07411(12) 0.07485(18) 0.27784(16) 0.0498(8) Uani 1.000 -16
C C12 0.04790(12) 0.06930(19) 0.42923(16) 0.0529(8) Uani 1.000 -16
C C13 0.11229(12) 0.01857(19) 0.51147(15) 0.0524(8) Uani 1.000 -16
C C14 0.16670(12) 0.07441(19) 0.58368(16) 0.0558(8) Uani 1.000 -16
C C15 0.23504(12) 0.03180(18) 0.66822(15) 0.0468(8) Uani 1.000 -16
C C16 0.28189(12) 0.10222(17) 0.74142(16) 0.0484(7) Uani 1.000 -16
C C17 0.34695(11) 0.06209(17) 0.82033(15) 0.0462(7) Uani 1.000 -16
C C18 0.36860(12) -0.04585(19) 0.83085(17) 0.0533(8) Uani 1.000 -16
C C19 0.32218(13) -0.11635(19) 0.75823(18) 0.0594(9) Uani 1.000 -16
C C20 0.25664(13) -0.07833(19) 0.67876(17) 0.0558(8) Uani 1.000 -16
H H2 -0.21290 -0.14941 0.09841 0.0664 Uiso 1.000 -16
H H2A 0.00843 0.19892 0.38131 0.0985 Uiso 1.000 -16
H H3 -0.32857 -0.13128 -0.04158 0.0726 Uiso 1.000 -16
H H5 -0.31886 0.19129 -0.01079 0.0749 Uiso 1.000 -16
H H6 -0.20295 0.17621 0.13074 0.0684 Uiso 1.000 -16
H H7A -0.41585 -0.01104 -0.17713 0.1210 Uiso 1.000 -16
H H7B -0.41647 0.11515 -0.15951 0.1210 Uiso 1.000 -16
H H7C -0.45667 0.03326 -0.12467 0.1210 Uiso 1.000 -16
H H9A 0.01385 -0.20300 0.43799 0.1245 Uiso 1.000 -16
H H9B 0.06423 -0.19504 0.39072 0.1245 Uiso 1.000 -16
H H9C -0.01457 -0.26184 0.34237 0.1245 Uiso 1.000 -16
H H13 0.11552 -0.05758 0.51357 0.0629 Uiso 1.000 -16
H H14 0.16074 0.15024 0.58025 0.0669 Uiso 1.000 -16
H H16 0.26930 0.17631 0.73710 0.0581 Uiso 1.000 -16
H H18 0.41302 -0.07088 0.88501 0.0640 Uiso 1.000 -16
H H19 0.33541 -0.19024 0.76316 0.0712 Uiso 1.000 -16
H H20 0.22594 -0.12729 0.63083 0.0669 Uiso 1.000 -16
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
C12 O2 H2A 109.00 no
N2 N1 C11 110.88(18) no
C1 N1 C11 130.70(18) no
N2 N1 C1 118.39(17) no
N1 N2 C8 107.02(18) no
O3 N3 C17 119.0(2) no
O4 N3 C17 118.1(2) no
O3 N3 O4 122.9(2) no
N1 C1 C6 121.2(2) no
C2 C1 C6 119.0(2) no
N1 C1 C2 119.8(2) no
C1 C2 C3 120.2(2) no
C2 C3 C4 122.3(2) no
C3 C4 C7 121.8(2) no
C5 C4 C7 121.5(2) no
C3 C4 C5 116.7(2) no
C4 C5 C6 122.6(2) no
C1 C6 C5 119.3(2) no
N2 C8 C9 119.4(2) no
N2 C8 C10 111.4(2) no
C9 C8 C10 129.3(2) no
C8 C10 C12 135.2(2) no
C11 C10 C12 120.0(2) no
C8 C10 C11 104.8(2) no
O1 C11 C10 127.3(2) no
N1 C11 C10 105.93(19) no
O1 C11 N1 126.7(2) no
O2 C12 C13 115.6(2) no
C10 C12 C13 125.7(2) no
O2 C12 C10 118.8(2) no
C12 C13 C14 123.6(2) no
C13 C14 C15 127.9(2) no
C14 C15 C20 122.5(2) no
C16 C15 C20 117.6(2) no
C14 C15 C16 119.9(2) no
C15 C16 C17 119.7(2) no
N3 C17 C18 118.9(2) no
C16 C17 C18 122.9(2) no
N3 C17 C16 118.21(19) no
C17 C18 C19 117.6(2) no
C18 C19 C20 120.6(2) no
C15 C20 C19 121.6(2) no
C1 C2 H2 120.00 no
C3 C2 H2 120.00 no
C2 C3 H3 119.00 no
C4 C3 H3 119.00 no
C4 C5 H5 119.00 no
C6 C5 H5 119.00 no
C1 C6 H6 120.00 no
C5 C6 H6 120.00 no
C4 C7 H7A 109.00 no
C4 C7 H7B 109.00 no
C4 C7 H7C 109.00 no
H7A C7 H7B 109.00 no
H7A C7 H7C 109.00 no
H7B C7 H7C 109.00 no
C8 C9 H9A 109.00 no
C8 C9 H9B 109.00 no
C8 C9 H9C 109.00 no
H9A C9 H9B 110.00 no
H9A C9 H9C 110.00 no
H9B C9 H9C 109.00 no
C12 C13 H13 118.00 no
C14 C13 H13 118.00 no
C13 C14 H14 116.00 no
C15 C14 H14 116.00 no
C15 C16 H16 120.00 no
C17 C16 H16 120.00 no
C17 C18 H18 121.00 no
C19 C18 H18 121.00 no
C18 C19 H19 120.00 no
C20 C19 H19 120.00 no
C15 C20 H20 119.00 no
C19 C20 H20 119.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C11 1.259(3) no
O2 C12 1.310(3) no
O3 N3 1.209(3) no
O4 N3 1.219(3) no
O2 H2A 0.8200 no
N1 C1 1.421(3) no
N1 C11 1.360(3) no
N1 N2 1.401(2) no
N2 C8 1.300(3) no
N3 C17 1.462(3) no
C1 C2 1.377(3) no
C1 C6 1.381(3) no
C2 C3 1.377(4) no
C3 C4 1.375(3) no
C4 C5 1.375(4) no
C4 C7 1.508(4) no
C5 C6 1.386(4) no
C8 C10 1.428(3) no
C8 C9 1.485(4) no
C10 C11 1.433(3) no
C10 C12 1.381(3) no
C12 C13 1.446(3) no
C13 C14 1.319(3) no
C14 C15 1.458(3) no
C15 C20 1.393(3) no
C15 C16 1.387(3) no
C16 C17 1.373(3) no
C17 C18 1.367(3) no
C18 C19 1.380(3) no
C19 C20 1.373(4) no
C2 H2 0.9300 no
C3 H3 0.9300 no
C5 H5 0.9300 no
C6 H6 0.9300 no
C7 H7A 0.9600 no
C7 H7B 0.9600 no
C7 H7C 0.9600 no
C9 H9A 0.9600 no
C9 H9B 0.9600 no
C9 H9C 0.9600 no
C13 H13 0.9300 no
C14 H14 0.9300 no
C16 H16 0.9300 no
C18 H18 0.9300 no
C19 H19 0.9300 no
C20 H20 0.9300 no
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
O2 H2A O1 . 0.82 1.82 2.571(3) 152 yes
C6 H6 O1 . 0.93 2.33 2.958(3) 125 yes
C18 H18 O4 3_657 0.93 2.57 3.496(3) 171 yes
C20 H20 O3 6_546 0.93 2.43 3.172(3) 136 yes
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
_geom_torsion_publ_flag
C1 N1 N2 C8 178.4(2) no
C11 N1 N2 C8 0.1(3) no
N2 N1 C1 C2 -3.6(4) no
N2 N1 C1 C6 176.3(2) no
C11 N1 C1 C2 174.2(3) no
C11 N1 C1 C6 -5.8(4) no
N2 N1 C11 O1 178.6(3) no
N2 N1 C11 C10 -1.2(3) no
C1 N1 C11 O1 0.6(5) no
C1 N1 C11 C10 -179.1(3) no
N1 N2 C8 C9 -178.7(2) no
N1 N2 C8 C10 1.0(3) no
O3 N3 C17 C16 14.1(4) no
O3 N3 C17 C18 -165.3(2) no
O4 N3 C17 C16 -166.5(2) no
O4 N3 C17 C18 14.1(4) no
N1 C1 C2 C3 179.2(2) no
C6 C1 C2 C3 -0.8(4) no
N1 C1 C6 C5 -179.4(3) no
C2 C1 C6 C5 0.6(4) no
C1 C2 C3 C4 0.6(4) no
C2 C3 C4 C5 -0.1(4) no
C2 C3 C4 C7 -179.4(3) no
C3 C4 C5 C6 -0.2(4) no
C7 C4 C5 C6 179.2(3) no
C4 C5 C6 C1 -0.1(4) no
N2 C8 C10 C11 -1.7(3) no
N2 C8 C10 C12 177.5(3) no
C9 C8 C10 C11 178.0(3) no
C9 C8 C10 C12 -2.8(5) no
C8 C10 C11 O1 -178.1(3) no
C8 C10 C11 N1 1.7(3) no
C12 C10 C11 O1 2.6(4) no
C12 C10 C11 N1 -177.7(2) no
C8 C10 C12 O2 179.6(3) no
C8 C10 C12 C13 -1.2(5) no
C11 C10 C12 O2 -1.3(4) no
C11 C10 C12 C13 177.9(3) no
O2 C12 C13 C14 2.3(4) no
C10 C12 C13 C14 -177.0(3) no
C12 C13 C14 C15 -177.9(3) no
C13 C14 C15 C16 -173.4(3) no
C13 C14 C15 C20 7.5(5) no
C14 C15 C16 C17 -178.9(2) no
C20 C15 C16 C17 0.2(4) no
C14 C15 C20 C19 178.6(3) no
C16 C15 C20 C19 -0.5(4) no
C15 C16 C17 N3 -179.2(2) no
C15 C16 C17 C18 0.1(4) no
N3 C17 C18 C19 179.2(2) no
C16 C17 C18 C19 -0.1(4) no
C17 C18 C19 C20 -0.2(4) no
C18 C19 C20 C15 0.5(4) no
