#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/79/2207929.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_2207929
loop_
_publ_author_name
'Liu, Guang-Fei'
'Peng, Bang-Hua'
'Liu, Lang'
'Jia, Dian-Zeng'
'Yu, Kai-Bei'
_publ_section_title
;
 5-Hydroxy-4-(4-methylbenzoyl)-1,3-diphenyl-1H-pyrazole
;
_journal_coeditor_code           WW6392
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o37
_journal_page_last               o38
_journal_paper_doi               10.1107/S1600536805039401
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C23 H18 N2 O2'
_chemical_formula_moiety         'C23 H18 N2 O2'
_chemical_formula_sum            'C23 H18 N2 O2'
_chemical_formula_weight         354.39
_chemical_name_systematic
;
5-Hydroxy-4-(4-methylbenzoyl)-1,3-diphenyl-1H-pyrazole
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                115.284(8)
_cell_angle_beta                 102.130(10)
_cell_angle_gamma                91.610(10)
_cell_formula_units_Z            2
_cell_length_a                   9.7050(10)
_cell_length_b                   10.0821(9)
_cell_length_c                   10.7460(10)
_cell_measurement_reflns_used    28
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      14.97
_cell_measurement_theta_min      3.89
_cell_volume                     921.21(17)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1994)'
_computing_data_reduction        'SHELXTL (Bruker, 1998)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0086
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4049
_diffrn_reflns_theta_full        25.25
_diffrn_reflns_theta_max         25.25
_diffrn_reflns_theta_min         2.16
_diffrn_standards_decay_%        4.76
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.117
_refine_ls_extinction_coef       0.045(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3307
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0365
_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)+(0.0522P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.0957
_reflns_number_gt                2233
_reflns_number_total             3307
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ww6392.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        921.2(2)
_cod_database_code               2207929
_cod_database_fobs_code          2207929
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_type_symbol
O1 0.53443(13) 0.68831(13) 0.19927(11) 0.0623(3) Uani d D 1 O
O2 0.35647(13) 0.83941(13) 0.32274(12) 0.0708(4) Uani d . 1 O
N1 0.68695(13) 0.61547(14) 0.35100(12) 0.0520(3) Uani d . 1 N
N2 0.71040(13) 0.63278(14) 0.48968(12) 0.0528(3) Uani d . 1 N
C1 0.73782(19) 0.4586(2) 0.12434(16) 0.0664(5) Uani d . 1 C
H1 0.6424 0.4467 0.0789 0.080 Uiso calc R 1 H
C2 0.8348(2) 0.3901(2) 0.04805(18) 0.0799(6) Uani d . 1 C
H2 0.8045 0.3329 -0.0496 0.096 Uiso calc R 1 H
C3 0.9750(2) 0.4057(2) 0.1150(2) 0.0844(6) Uani d . 1 C
H3 1.0395 0.3585 0.0632 0.101 Uiso calc R 1 H
C4 1.0197(2) 0.4910(2) 0.2582(2) 0.0901(7) Uani d . 1 C
H4 1.1150 0.5016 0.3036 0.108 Uiso calc R 1 H
C5 0.92513(19) 0.5617(2) 0.33635(19) 0.0746(5) Uani d . 1 C
H5 0.9561 0.6201 0.4338 0.090 Uiso calc R 1 H
C6 0.78463(17) 0.54439(17) 0.26812(15) 0.0533(4) Uani d . 1 C
C7 0.57692(16) 0.68320(16) 0.32192(14) 0.0478(4) Uani d D 1 C
C8 0.51969(15) 0.74366(15) 0.44019(14) 0.0452(4) Uani d . 1 C
C9 0.61152(16) 0.70866(16) 0.54247(14) 0.0451(4) Uani d . 1 C
C10 0.61703(14) 0.75032(16) 0.69331(14) 0.0439(4) Uani d . 1 C
C11 0.62524(16) 0.64372(18) 0.74239(16) 0.0539(4) Uani d . 1 C
H11 0.6222 0.5451 0.6791 0.065 Uiso calc R 1 H
C12 0.63783(18) 0.6819(2) 0.88412(18) 0.0654(5) Uani d . 1 C
H12 0.6422 0.6091 0.9157 0.079 Uiso calc R 1 H
C13 0.64387(18) 0.8269(2) 0.97814(17) 0.0688(5) Uani d . 1 C
H13 0.6525 0.8529 1.0738 0.083 Uiso calc R 1 H
C14 0.63716(19) 0.9340(2) 0.93079(16) 0.0659(5) Uani d . 1 C
H14 0.6426 1.0327 0.9950 0.079 Uiso calc R 1 H
C15 0.62256(17) 0.89636(18) 0.78947(16) 0.0549(4) Uani d . 1 C
H15 0.6164 0.9695 0.7583 0.066 Uiso calc R 1 H
C16 0.39436(16) 0.81483(16) 0.43021(15) 0.0497(4) Uani d . 1 C
C17 0.30364(15) 0.85520(16) 0.53170(15) 0.0476(4) Uani d . 1 C
C18 0.22801(17) 0.97470(18) 0.54930(17) 0.0582(4) Uani d . 1 C
H18 0.2398 1.0306 0.5014 0.070 Uiso calc R 1 H
C19 0.13562(19) 1.0110(2) 0.63714(19) 0.0676(5) Uani d . 1 C
H19 0.0887 1.0934 0.6503 0.081 Uiso calc R 1 H
C20 0.11181(17) 0.9268(2) 0.70582(17) 0.0654(5) Uani d . 1 C
C21 0.18616(18) 0.8073(2) 0.68691(17) 0.0625(5) Uani d . 1 C
H21 0.1715 0.7494 0.7323 0.075 Uiso calc R 1 H
C22 0.28165(16) 0.77185(18) 0.60216(15) 0.0534(4) Uani d . 1 C
H22 0.3314 0.6919 0.5923 0.064 Uiso calc R 1 H
C23 0.0065(2) 0.9634(3) 0.7970(2) 0.0995(7) Uani d . 1 C
H23A -0.0344 1.0492 0.7977 0.119 Uiso calc PR 0.50 H
H23B 0.0543 0.9830 0.8921 0.119 Uiso calc PR 0.50 H
H23C -0.0673 0.8812 0.7592 0.119 Uiso calc PR 0.50 H
H23D 0.0028 0.8931 0.8349 0.119 Uiso calc PR 0.50 H
H23E -0.0859 0.9592 0.7405 0.119 Uiso calc PR 0.50 H
H23F 0.0357 1.0611 0.8735 0.119 Uiso calc PR 0.50 H
H1O 0.4642(18) 0.745(2) 0.2034(16) 0.113(8) Uiso d D 1 H
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
C7 O1 H1O 109.5(9) ?
C7 N1 N2 110.47(11) yes
C7 N1 C6 130.20(12) ?
N2 N1 C6 119.06(12) ?
C9 N2 N1 106.01(12) yes
C6 C1 C2 118.97(16) ?
C6 C1 H1 120.5 ?
C2 C1 H1 120.5 ?
C3 C2 C1 120.61(17) ?
C3 C2 H2 119.7 ?
C1 C2 H2 119.7 ?
C4 C3 C2 119.67(17) ?
C4 C3 H3 120.2 ?
C2 C3 H3 120.2 ?
C3 C4 C5 120.78(18) ?
C3 C4 H4 119.6 ?
C5 C4 H4 119.6 ?
C6 C5 C4 119.00(17) ?
C6 C5 H5 120.5 ?
C4 C5 H5 120.5 ?
C1 C6 C5 120.96(15) ?
C1 C6 N1 120.57(14) ?
C5 C6 N1 118.46(14) ?
O1 C7 N1 123.18(13) yes
O1 C7 C8 128.05(14) yes
N1 C7 C8 108.77(12) yes
C7 C8 C9 103.31(13) yes
C7 C8 C16 118.56(13) yes
C9 C8 C16 138.11(13) ?
N2 C9 C8 111.39(12) yes
N2 C9 C10 117.21(12) ?
C8 C9 C10 131.29(13) ?
C11 C10 C15 118.62(13) ?
C11 C10 C9 120.08(13) ?
C15 C10 C9 121.19(13) ?
C12 C11 C10 120.79(15) ?
C12 C11 H11 119.6 ?
C10 C11 H11 119.6 ?
C13 C12 C11 119.95(16) ?
C13 C12 H12 120.0 ?
C11 C12 H12 120.0 ?
C12 C13 C14 119.78(15) ?
C12 C13 H13 120.1 ?
C14 C13 H13 120.1 ?
C15 C14 C13 120.51(16) ?
C15 C14 H14 119.7 ?
C13 C14 H14 119.7 ?
C14 C15 C10 120.34(15) ?
C14 C15 H15 119.8 ?
C10 C15 H15 119.8 ?
O2 C16 C8 117.03(13) yes
O2 C16 C17 117.74(13) ?
C8 C16 C17 125.17(13) ?
C22 C17 C18 118.39(15) ?
C22 C17 C16 122.59(14) ?
C18 C17 C16 118.82(14) ?
C19 C18 C17 120.69(16) ?
C19 C18 H18 119.7 ?
C17 C18 H18 119.7 ?
C18 C19 C20 121.03(16) ?
C18 C19 H19 119.5 ?
C20 C19 H19 119.5 ?
C21 C20 C19 118.04(16) ?
C21 C20 C23 121.15(19) ?
C19 C20 C23 120.80(18) ?
C22 C21 C20 121.54(17) ?
C22 C21 H21 119.2 ?
C20 C21 H21 119.2 ?
C21 C22 C17 120.27(15) ?
C21 C22 H22 119.9 ?
C17 C22 H22 119.9 ?
C20 C23 H23A 109.5 ?
C20 C23 H23B 109.5 ?
H23A C23 H23B 109.5 ?
C20 C23 H23C 109.5 ?
H23A C23 H23C 109.5 ?
H23B C23 H23C 109.5 ?
C20 C23 H23D 109.5 ?
H23A C23 H23D 141.1 ?
H23B C23 H23D 56.3 ?
H23C C23 H23D 56.3 ?
C20 C23 H23E 109.5 ?
H23A C23 H23E 56.3 ?
H23B C23 H23E 141.1 ?
H23C C23 H23E 56.3 ?
H23D C23 H23E 109.5 ?
C20 C23 H23F 109.5 ?
H23A C23 H23F 56.3 ?
H23B C23 H23F 56.3 ?
H23C C23 H23F 141.1 ?
H23D C23 H23F 109.5 ?
H23E C23 H23F 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C7 1.3193(16) yes
O1 H1O 0.898(19) ?
O2 C16 1.2655(17) yes
N1 C7 1.3369(19) yes
N1 N2 1.3915(16) yes
N1 C6 1.4330(19) ?
N2 C9 1.3142(18) yes
C1 C6 1.372(2) ?
C1 C2 1.383(2) ?
C1 H1 0.9300 ?
C2 C3 1.368(3) ?
C2 H2 0.9300 ?
C3 C4 1.365(3) ?
C3 H3 0.9300 ?
C4 C5 1.380(2) ?
C4 H4 0.9300 ?
C5 C6 1.373(2) ?
C5 H5 0.9300 ?
C7 C8 1.3962(19) yes
C8 C9 1.4366(19) yes
C8 C16 1.437(2) ?
C9 C10 1.4791(18) ?
C10 C11 1.382(2) ?
C10 C15 1.383(2) ?
C11 C12 1.379(2) ?
C11 H11 0.9300 ?
C12 C13 1.367(2) ?
C12 H12 0.9300 ?
C13 C14 1.374(2) ?
C13 H13 0.9300 ?
C14 C15 1.373(2) ?
C14 H14 0.9300 ?
C15 H15 0.9300 ?
C16 C17 1.475(2) ?
C17 C22 1.388(2) ?
C17 C18 1.393(2) ?
C18 C19 1.381(2) ?
C18 H18 0.9300 ?
C19 C20 1.384(3) ?
C19 H19 0.9300 ?
C20 C21 1.384(2) ?
C20 C23 1.508(2) ?
C21 C22 1.382(2) ?
C21 H21 0.9300 ?
C22 H22 0.9300 ?
C23 H23A 0.9600 ?
C23 H23B 0.9600 ?
C23 H23C 0.9600 ?
C23 H23D 0.9600 ?
C23 H23E 0.9600 ?
C23 H23F 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
_geom_hbond_publ_flag
O1 H1O O2 . 0.898(19) 1.794(14) 2.5394(16) 138.7(12) y
C15 H15 O2 2_676 0.93 2.46 3.378(2) 170 y
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 1.36(17)
C6 N1 N2 C9 176.03(13)
C6 C1 C2 C3 0.9(3)
C1 C2 C3 C4 -0.7(3)
C2 C3 C4 C5 0.1(4)
C3 C4 C5 C6 0.4(3)
C2 C1 C6 C5 -0.5(3)
C2 C1 C6 N1 -179.15(15)
C4 C5 C6 C1 -0.1(3)
C4 C5 C6 N1 178.55(17)
C7 N1 C6 C1 -40.2(3)
N2 N1 C6 C1 146.30(15)
C7 N1 C6 C5 141.11(18)
N2 N1 C6 C5 -32.4(2)
N2 N1 C7 O1 177.74(13)
C6 N1 C7 O1 3.8(3)
N2 N1 C7 C8 -2.25(17)
C6 N1 C7 C8 -176.15(14)
O1 C7 C8 C9 -177.86(15)
N1 C7 C8 C9 2.12(16)
O1 C7 C8 C16 3.6(2)
N1 C7 C8 C16 -176.40(13)
N1 N2 C9 C8 0.05(16)
N1 N2 C9 C10 -176.59(12)
C7 C8 C9 N2 -1.33(16)
C16 C8 C9 N2 176.73(17)
C7 C8 C9 C10 174.70(15)
C16 C8 C9 C10 -7.2(3)
N2 C9 C10 C11 -51.95(19)
C8 C9 C10 C11 132.21(16)
N2 C9 C10 C15 124.20(16)
C8 C9 C10 C15 -51.6(2)
C15 C10 C11 C12 0.4(2)
C9 C10 C11 C12 176.64(14)
C10 C11 C12 C13 -0.7(2)
C11 C12 C13 C14 0.1(3)
C12 C13 C14 C15 0.9(3)
C13 C14 C15 C10 -1.2(3)
C11 C10 C15 C14 0.6(2)
C9 C10 C15 C14 -175.65(15)
C7 C8 C16 O2 -11.0(2)
C9 C8 C16 O2 171.10(16)
C7 C8 C16 C17 166.13(14)
C9 C8 C16 C17 -11.7(3)
O2 C16 C17 C22 143.95(15)
C8 C16 C17 C22 -33.2(2)
O2 C16 C17 C18 -30.8(2)
C8 C16 C17 C18 152.03(14)
C22 C17 C18 C19 1.3(2)
C16 C17 C18 C19 176.29(14)
C17 C18 C19 C20 -2.4(2)
C18 C19 C20 C21 1.7(2)
C18 C19 C20 C23 -177.57(16)
C19 C20 C21 C22 0.0(2)
C23 C20 C21 C22 179.23(16)
C20 C21 C22 C17 -1.0(2)
C18 C17 C22 C21 0.3(2)
C16 C17 C22 C21 -174.45(14)
