#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/42/2234245.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_2234245
loop_
_publ_author_name
'Wardell, Solange M. S. V.'
'Howie, Alan H.'
'Tiekink, Edward R. T.'
'Wardell, James L.'
_publ_section_title
;
 4-[3,4-Dimethyl-1-(4-methylphenyl)-5-oxo-4,5-dihydro-1H-pyrazol-4-yl]-3,4-dimethyl-1-(4-methylphenyl)-4,5-dihydro-1H-pyrazol-5-one
;
_journal_coeditor_code           HG5185
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o992
_journal_page_last               o993
_journal_paper_doi               10.1107/S1600536812009208
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C24 H26 N4 O2'
_chemical_formula_moiety         'C24 H26 N4 O2'
_chemical_formula_sum            'C24 H26 N4 O2'
_chemical_formula_weight         402.50
_chemical_name_systematic
;
4-[3,4-Dimethyl-1-(4-methylphenyl)-5-oxo-4,5-dihydro-1H-pyrazol-4-yl]-
3,4-dimethyl-1-(4-methylphenyl)-4,5-dihydro-1H-pyrazol-5-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                 92.566(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   23.0007(8)
_cell_length_b                   6.6712(2)
_cell_length_c                   13.5967(5)
_cell_measurement_reflns_used    6506
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     2084.22(12)
_computing_cell_refinement
;
CrystalClear-SM Expert (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert (Rigaku, 2011)
;
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724+
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_sigmaI/netI    0.0377
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11383
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.00
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6679
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'(CrystalClear-SM Expert; Rigaku, 2011)'
_exptl_crystal_colour            light-yellow
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.178
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.829
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2384
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.829
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0415
_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)+(0.1040P)²+1.4411P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1197
_refine_ls_wR_factor_ref         0.1359
_reflns_number_gt                1856
_reflns_number_total             2384
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg5185.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     '-C 2yc '
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2234245
_cod_database_fobs_code          2234245
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_symmetry_multiplicity
O O1 0.06343(4) 0.52970(14) 0.91141(7) 0.0292(3) Uani d . 1 1
N N1 0.10162(5) 0.23866(16) 0.84739(8) 0.0202(3) Uani d . 1 1
N N2 0.09381(5) 0.12079(17) 0.76120(8) 0.0217(3) Uani d . 1 1
C C1 0.05610(5) 0.2093(2) 0.70361(9) 0.0194(3) Uani d . 1 1
C C2 0.03383(5) 0.40353(18) 0.74559(9) 0.0197(3) Uani d . 1 1
C C3 0.06614(6) 0.40447(19) 0.84662(9) 0.0205(3) Uani d . 1 1
C C4 0.03921(6) 0.1236(2) 0.60511(9) 0.0253(3) Uani d . 1 1
H H4A 0.0658 0.0144 0.5900 0.038 Uiso calc R 1 1
H H4B 0.0413 0.2284 0.5549 0.038 Uiso calc R 1 1
H H4C -0.0006 0.0718 0.6057 0.038 Uiso calc R 1 1
C C5 0.05690(7) 0.5851(2) 0.68862(11) 0.0310(3) Uani d . 1 1
H H5A 0.0993 0.5753 0.6856 0.046 Uiso calc R 1 1
H H5B 0.0468 0.7092 0.7224 0.046 Uiso calc R 1 1
H H5C 0.0392 0.5861 0.6217 0.046 Uiso calc R 1 1
C C6 0.13732(5) 0.1626(2) 0.92676(9) 0.0198(3) Uani d . 1 1
C C7 0.15049(6) -0.0403(2) 0.93131(10) 0.0245(3) Uani d . 1 1
H H7 0.1366 -0.1285 0.8807 0.029 Uiso calc R 1 1
C C8 0.18434(6) -0.1132(2) 1.01097(10) 0.0271(3) Uani d . 1 1
H H8 0.1931 -0.2523 1.0140 0.033 Uiso calc R 1 1
C C9 0.20565(6) 0.0114(2) 1.08617(9) 0.0258(3) Uani d . 1 1
C C10 0.19226(6) 0.2144(2) 1.07910(10) 0.0282(3) Uani d . 1 1
H H10 0.2065 0.3028 1.1294 0.034 Uiso calc R 1 1
C C11 0.15862(6) 0.2913(2) 1.00071(10) 0.0253(3) Uani d . 1 1
H H11 0.1502 0.4306 0.9974 0.030 Uiso calc R 1 1
C C12 0.24118(7) -0.0698(3) 1.17294(10) 0.0350(4) Uani d . 1 1
H H12A 0.2499 -0.2116 1.1618 0.052 Uiso calc R 1 1
H H12B 0.2191 -0.0564 1.2326 0.052 Uiso calc R 1 1
H H12C 0.2776 0.0057 1.1809 0.052 Uiso calc R 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 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_3
_geom_angle
C3 N1 N2 . 112.79(10)
C3 N1 C6 . 128.04(11)
N2 N1 C6 . 118.56(10)
C1 N2 N1 . 107.82(10)
N2 C1 C4 . 120.81(12)
N2 C1 C2 . 113.19(11)
C4 C1 C2 . 125.98(11)
C1 C2 C3 . 100.53(10)
C1 C2 C5 . 110.64(10)
C3 C2 C5 . 106.41(10)
C1 C2 C2 2_556 112.51(8)
C3 C2 C2 2_556 112.02(12)
C5 C2 C2 2_556 113.78(9)
O1 C3 N1 . 126.61(12)
O1 C3 C2 . 127.80(12)
N1 C3 C2 . 105.52(10)
C1 C4 H4A . 109.5
C1 C4 H4B . 109.5
H4A C4 H4B . 109.5
C1 C4 H4C . 109.5
H4A C4 H4C . 109.5
H4B C4 H4C . 109.5
C2 C5 H5A . 109.5
C2 C5 H5B . 109.5
H5A C5 H5B . 109.5
C2 C5 H5C . 109.5
H5A C5 H5C . 109.5
H5B C5 H5C . 109.5
C7 C6 C11 . 119.98(12)
C7 C6 N1 . 119.99(12)
C11 C6 N1 . 120.03(12)
C6 C7 C8 . 119.23(13)
C6 C7 H7 . 120.4
C8 C7 H7 . 120.4
C9 C8 C7 . 121.98(13)
C9 C8 H8 . 119.0
C7 C8 H8 . 119.0
C8 C9 C10 . 117.50(13)
C8 C9 C12 . 121.48(14)
C10 C9 C12 . 121.02(13)
C11 C10 C9 . 121.84(13)
C11 C10 H10 . 119.1
C9 C10 H10 . 119.1
C10 C11 C6 . 119.47(13)
C10 C11 H11 . 120.3
C6 C11 H11 . 120.3
C9 C12 H12A . 109.5
C9 C12 H12B . 109.5
H12A C12 H12B . 109.5
C9 C12 H12C . 109.5
H12A C12 H12C . 109.5
H12B C12 H12C . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C3 . 1.2177(15)
N1 C3 . 1.3743(17)
N1 N2 . 1.4160(14)
N1 C6 . 1.4202(16)
N2 C1 . 1.2859(17)
C1 C4 . 1.4917(17)
C1 C2 . 1.5142(17)
C2 C3 . 1.5323(17)
C2 C5 . 1.5446(18)
C2 C2 2_556 1.566(3)
C4 H4A . 0.9800
C4 H4B . 0.9800
C4 H4C . 0.9800
C5 H5A . 0.9800
C5 H5B . 0.9800
C5 H5C . 0.9800
C6 C7 . 1.3882(19)
C6 C11 . 1.3943(18)
C7 C8 . 1.3928(18)
C7 H7 . 0.9500
C8 C9 . 1.390(2)
C8 H8 . 0.9500
C9 C10 . 1.391(2)
C9 C12 . 1.5057(19)
C10 C11 . 1.3873(19)
C10 H10 . 0.9500
C11 H11 . 0.9500
C12 H12A . 0.9800
C12 H12B . 0.9800
C12 H12C . 0.9800
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
C4 H4B O1 6_565 0.98 2.60 3.5676(16) 169
C4 H4A Cg1 4_554 0.98 2.82 3.6644(15) 145
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_4
_geom_torsion
C3 N1 N2 C1 . . 2.35(15)
C6 N1 N2 C1 . . 174.14(10)
N1 N2 C1 C4 . . 178.79(11)
N1 N2 C1 C2 . . 0.36(14)
N2 C1 C2 C3 . . -2.51(13)
C4 C1 C2 C3 . . 179.15(12)
N2 C1 C2 C5 . . 109.65(13)
C4 C1 C2 C5 . . -68.69(16)
N2 C1 C2 C2 . 2_556 -121.85(13)
C4 C1 C2 C2 . 2_556 59.82(17)
N2 N1 C3 O1 . . 179.21(12)
C6 N1 C3 O1 . . 8.4(2)
N2 N1 C3 C2 . . -3.87(13)
C6 N1 C3 C2 . . -174.71(11)
C1 C2 C3 O1 . . -179.48(13)
C5 C2 C3 O1 . . 65.14(17)
C2 C2 C3 O1 2_556 . -59.80(14)
C1 C2 C3 N1 . . 3.64(12)
C5 C2 C3 N1 . . -111.74(12)
C2 C2 C3 N1 2_556 . 123.33(8)
C3 N1 C6 C7 . . 152.61(13)
N2 N1 C6 C7 . . -17.78(17)
C3 N1 C6 C11 . . -26.66(19)
N2 N1 C6 C11 . . 162.95(11)
C11 C6 C7 C8 . . 0.90(19)
N1 C6 C7 C8 . . -178.37(11)
C6 C7 C8 C9 . . -0.3(2)
C7 C8 C9 C10 . . -0.4(2)
C7 C8 C9 C12 . . 178.74(12)
C8 C9 C10 C11 . . 0.4(2)
C12 C9 C10 C11 . . -178.70(13)
C9 C10 C11 C6 . . 0.2(2)
C7 C6 C11 C10 . . -0.9(2)
N1 C6 C11 C10 . . 178.41(11)
