##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
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##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
4-Benzoyl-1,5-diphenyl-1H-pyrazole-3-carboxylic acid methanol solvate
;
_chemical_name_common     ?
_chemical_formula_moiety     'C23 H16 N2 O3, C H4 O'
_chemical_formula_sum     'C24 H20 N2 O4'
_chemical_formula_iupac     'C23 H16 N2 O3, C H4 O'
_chemical_formula_weight     400.42
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P c a b'
_symmetry_space_group_name_Hall     '-P 2bc 2ac'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y+1/2, z+1/2'
    'x+1/2, -y, -z+1/2'
    '-x+1/2, y+1/2, -z'
    '-x, -y, -z'
    'x, y-1/2, -z-1/2'
    '-x-1/2, y, z-1/2'
    'x-1/2, -y-1/2, z'
_cell_length_a     10.8731(9)
_cell_length_b     18.7861(14)
_cell_length_c     20.5836(19)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     4204.5(6)
_cell_formula_units_Z     8
_cell_measurement_reflns_used     8043
_cell_measurement_theta_min     1.98
_cell_measurement_theta_max     24.47
_cell_measurement_temperature     293(2)
_exptl_crystal_description     'prism'
_exptl_crystal_colour     'colorless'
_exptl_crystal_size_max     0.50
_exptl_crystal_size_mid     0.33
_exptl_crystal_size_min     0.21
_exptl_crystal_density_diffrn     1.265
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1680
_exptl_absorpt_coefficient_mu     0.087
_exptl_absorpt_correction_type     integration
_exptl_absorpt_process_details     '(X-RED; Stoe & Cie, 2002)'
_exptl_absorpt_correction_T_min     0.9653
_exptl_absorpt_correction_T_max     0.9838
_exptl_special_details
;
 Experiments were followed by thin layer chromatography using a DC Alufolien
 Kieselgel 60 F254 Merck and Camag TLC lamp (254/366nm). After completion of the
 reactions, solvents were evaporated with a rotary evaporator (Buchi RE model
 111). The melting point was determined on an Electrothermal 9200 apparatus and
 is uncorrected. Microanalysis was performed with a Carlo Erba Elemental
 Analyser Model 1108.
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'sealed X-ray tube'
_diffrn_radiation_monochromator     'plane graphite'
_diffrn_measurement_device_type     'Stoe IPDS-II'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     6.67
_diffrn_reflns_number     27164
_diffrn_reflns_av_R_equivalents     0.0993
_diffrn_reflns_av_sigmaI/netI     0.0744
_diffrn_reflns_theta_min     1.98
_diffrn_reflns_theta_max     25.49
_diffrn_reflns_theta_full     25.49
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     -22
_diffrn_reflns_limit_k_max     22
_diffrn_reflns_limit_l_min     -24
_diffrn_reflns_limit_l_max     24
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     3914
_reflns_number_gt     1743
_reflns_threshold_expression     'I>2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1046
_refine_ls_R_factor_gt     0.0430
_refine_ls_wR_factor_gt     0.0738
_refine_ls_wR_factor_ref     0.0792
_refine_ls_goodness_of_fit_ref     1.000
_refine_ls_restrained_S_all     0.966
_refine_ls_number_reflns     3914
_refine_ls_number_parameters     327
_refine_ls_number_restraints     417
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0154P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     '<0.001'
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.110
_refine_diff_density_min     -0.198
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'X-AREA (Stoe & Cie, 2002)'
_computing_cell_refinement     'X-AREA'
_computing_data_reduction     'X-RED32 (Stoe & Cie, 2002)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material
                                'WinGX (Farrugia, 1999) and PLATON (Spek, 2003)'
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_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
    O1 0.31931(15) 0.16088(9) 0.01148(6) 0.0829(5) Uani d DU 1 A . O
    O2A 0.4548(13) 0.0740(7) 0.0159(5) 0.081(3) Uani d PDU 0.509(11) A 1 O
    H2A 0.4347 0.0681 -0.0222 0.122 Uiso calc PR 0.509(11) A 1 H
    O2B 0.4315(16) 0.0629(8) 0.0219(6) 0.115(5) Uani d PDU 0.491(11) A 2 O
    H2B 0.4129 0.0564 -0.0163 0.173 Uiso calc PR 0.491(11) A 2 H
    O3 0.21399(15) 0.26963(10) 0.16199(6) 0.0878(6) Uani d U 1 . . O
    O4 0.39288(18) 0.03190(9) -0.09865(7) 0.0975(6) Uani d U 1 . . O
    H4 0.4297 -0.0041 -0.1100 0.146 Uiso calc R 1 . . H
    N1 0.48907(16) 0.11614(10) 0.20537(7) 0.0573(5) Uani d U 1 . . N
    N2 0.48245(16) 0.08894(10) 0.14406(7) 0.0609(5) Uani d U 1 . . N
    C1 0.42035(18) 0.13814(12) 0.11104(8) 0.0530(5) Uani d DU 1 A . C
    C2 0.38444(18) 0.19565(11) 0.14977(8) 0.0526(5) Uani d U 1 . . C
    C3 0.43055(19) 0.17899(12) 0.21078(8) 0.0537(5) Uani d U 1 A . C
    C4 0.3884(2) 0.12443(14) 0.04116(9) 0.0606(6) Uani d DU 1 . . C
    C5 0.3098(2) 0.25859(12) 0.13308(9) 0.0574(6) Uani d U 1 . . C
    C6 0.3535(2) 0.30809(12) 0.08170(9) 0.0542(5) Uani d U 1 . . C
    C7 0.2708(2) 0.35376(14) 0.05310(10) 0.0796(7) Uani d U 1 . . C
    H7 0.1886 0.3531 0.0657 0.096 Uiso calc R 1 . . H
    C8 0.3097(3) 0.40072(16) 0.00547(12) 0.1021(9) Uani d U 1 . . C
    H8 0.2537 0.4311 -0.0144 0.123 Uiso calc R 1 . . H
    C9 0.4299(3) 0.40219(16) -0.01208(12) 0.1001(9) Uani d U 1 . . C
    H9 0.4555 0.4339 -0.0440 0.120 Uiso calc R 1 . . H
    C10 0.5141(2) 0.35795(14) 0.01620(11) 0.0860(8) Uani d U 1 . . C
    H10 0.5966 0.3601 0.0044 0.103 Uiso calc R 1 . . H
    C11 0.4743(2) 0.30956(13) 0.06292(9) 0.0658(6) Uani d U 1 . . C
    H11 0.5301 0.2780 0.0815 0.079 Uiso calc R 1 . . H
    C12 0.4252(2) 0.21998(13) 0.27227(9) 0.0596(6) Uani d DU 1 . . C
    C13A 0.4835(7) 0.2870(4) 0.2712(4) 0.078(2) Uani d PDU 0.509(11) A 1 C
    H13A 0.5222 0.3034 0.2338 0.093 Uiso calc PR 0.509(11) A 1 H
    C14A 0.4815(7) 0.3278(5) 0.3275(4) 0.096(3) Uani d PDU 0.509(11) A 1 C
    H14A 0.5224 0.3713 0.3289 0.115 Uiso calc PR 0.509(11) A 1 H
    C15A 0.4201(13) 0.3042(7) 0.3804(5) 0.096(3) Uani d PDU 0.509(11) A 1 C
    H15A 0.4200 0.3313 0.4182 0.115 Uiso calc PR 0.509(11) A 1 H
    C16A 0.3584(12) 0.2413(7) 0.3788(5) 0.100(4) Uani d PDU 0.509(11) A 1 C
    H16A 0.3146 0.2265 0.4152 0.120 Uiso calc PR 0.509(11) A 1 H
    C17A 0.3598(11) 0.1992(7) 0.3237(5) 0.096(4) Uani d PDU 0.509(11) A 1 C
    H17A 0.3156 0.1568 0.3225 0.115 Uiso calc PR 0.509(11) A 1 H
    C13B 0.5215(8) 0.2546(6) 0.2994(4) 0.111(3) Uani d PDU 0.491(11) A 2 C
    H13B 0.5965 0.2558 0.2777 0.133 Uiso calc PR 0.491(11) A 2 H
    C14B 0.5100(9) 0.2885(7) 0.3595(5) 0.129(4) Uani d PDU 0.491(11) A 2 C
    H14B 0.5750 0.3152 0.3760 0.154 Uiso calc PR 0.491(11) A 2 H
    C15B 0.4043(15) 0.2824(9) 0.3934(6) 0.104(4) Uani d PDU 0.491(11) A 2 C
    H15B 0.3992 0.3027 0.4346 0.124 Uiso calc PR 0.491(11) A 2 H
    C16B 0.3050(11) 0.2474(8) 0.3689(6) 0.104(4) Uani d PDU 0.491(11) A 2 C
    H16B 0.2305 0.2463 0.3911 0.125 Uiso calc PR 0.491(11) A 2 H
    C17B 0.3196(10) 0.2132(7) 0.3092(5) 0.075(3) Uani d PDU 0.491(11) A 2 C
    H17B 0.2559 0.1848 0.2936 0.090 Uiso calc PR 0.491(11) A 2 H
    C18 0.5503(2) 0.07337(13) 0.25426(8) 0.0567(6) Uani d U 1 . . C
    C19 0.6554(2) 0.09568(15) 0.28198(10) 0.0820(8) Uani d U 1 . . C
    H19 0.6893 0.1395 0.2711 0.098 Uiso calc R 1 . . H
    C20 0.7120(3) 0.0518(2) 0.32709(11) 0.0998(10) Uani d U 1 . . C
    H20 0.7853 0.0661 0.3463 0.120 Uiso calc R 1 . . H
    C21 0.6621(3) -0.0111(2) 0.34331(12) 0.1005(10) Uani d U 1 . . C
    H21 0.7011 -0.0400 0.3736 0.121 Uiso calc R 1 . . H
    C22 0.5557(3) -0.03254(16) 0.31578(13) 0.1071(10) Uani d U 1 . . C
    H22 0.5217 -0.0762 0.3272 0.129 Uiso calc R 1 . . H
    C23 0.4968(2) 0.01023(15) 0.27060(10) 0.0836(8) Uani d U 1 . . C
    H23 0.4228 -0.0038 0.2519 0.100 Uiso calc R 1 . . H
    C24 0.2783(3) 0.03358(17) -0.12805(13) 0.1319(12) Uani d U 1 . . C
    H24A 0.2240 0.0632 -0.1032 0.158 Uiso calc R 1 . . H
    H24B 0.2455 -0.0138 -0.1302 0.158 Uiso calc R 1 . . H
    H24C 0.2861 0.0525 -0.1712 0.158 Uiso calc R 1 . . H
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C4 . 1.186(2) yes
    O2A C4 . 1.300(6) yes
    O2A H2A . 0.8200 ?
    O2B C4 . 1.308(8) yes
    O2B H2B . 0.8200 ?
    O3 C5 . 1.218(2) yes
    O4 C24 . 1.385(3) yes
    O4 H4 . 0.8200 ?
    N1 C3 . 1.346(2) yes
    N1 N2 . 1.3634(18) yes
    N1 C18 . 1.449(2) yes
    N2 C1 . 1.331(2) yes
    C1 C2 . 1.398(3) yes
    C1 C4 . 1.502(3) yes
    C2 C3 . 1.388(2) yes
    C2 C5 . 1.475(3) yes
    C3 C12 . 1.483(3) yes
    C5 C6 . 1.486(3) ?
    C6 C11 . 1.369(3) ?
    C6 C7 . 1.376(3) ?
    C7 C8 . 1.385(3) ?
    C7 H7 . 0.9300 ?
    C8 C9 . 1.356(3) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.367(3) ?
    C9 H9 . 0.9300 ?
    C10 C11 . 1.392(3) ?
    C10 H10 . 0.9300 ?
    C11 H11 . 0.9300 ?
    C12 C17A . 1.333(9) ?
    C12 C13B . 1.353(7) ?
    C12 C17B . 1.383(9) ?
    C12 C13A . 1.410(6) ?
    C13A C14A . 1.390(7) ?
    C13A H13A . 0.9300 ?
    C14A C15A . 1.351(9) ?
    C14A H14A . 0.9300 ?
    C15A C16A . 1.359(11) ?
    C15A H15A . 0.9300 ?
    C16A C17A . 1.383(9) ?
    C16A H16A . 0.9300 ?
    C17A H17A . 0.9300 ?
    C13B C14B . 1.397(8) ?
    C13B H13B . 0.9300 ?
    C14B C15B . 1.350(11) ?
    C14B H14B . 0.9300 ?
    C15B C16B . 1.361(12) ?
    C15B H15B . 0.9300 ?
    C16B C17B . 1.397(10) ?
    C16B H16B . 0.9300 ?
    C17B H17B . 0.9300 ?
    C18 C19 . 1.345(3) ?
    C18 C23 . 1.363(3) ?
    C19 C20 . 1.386(3) ?
    C19 H19 . 0.9300 ?
    C20 C21 . 1.342(4) ?
    C20 H20 . 0.9300 ?
    C21 C22 . 1.350(4) ?
    C21 H21 . 0.9300 ?
    C22 C23 . 1.385(3) ?
    C22 H22 . 0.9300 ?
    C23 H23 . 0.9300 ?
    C24 H24A . 0.9600 ?
    C24 H24B . 0.9600 ?
    C24 H24C . 0.9600 ?
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
    C4 O2A H2A . . 109.5 ?
    C4 O2B H2B . . 109.5 ?
    C24 O4 H4 . . 109.5 ?
    C3 N1 N2 . . 112.36(15) yes
    C3 N1 C18 . . 130.22(16) yes
    N2 N1 C18 . . 117.33(18) yes
    C1 N2 N1 . . 103.84(16) yes
    N2 C1 C2 . . 112.77(15) yes
    N2 C1 C4 . . 119.16(19) yes
    C2 C1 C4 . . 127.9(2) yes
    C3 C2 C1 . . 103.93(18) yes
    C3 C2 C5 . . 126.19(18) yes
    C1 C2 C5 . . 129.81(17) yes
    N1 C3 C2 . . 107.07(17) yes
    N1 C3 C12 . . 123.02(17) yes
    C2 C3 C12 . . 129.9(2) yes
    O1 C4 O2A . . 124.5(4) yes
    O1 C4 O2B . . 125.5(5) yes
    O1 C4 C1 . . 122.7(2) yes
    O2A C4 C1 . . 112.3(4) yes
    O2B C4 C1 . . 111.0(5) yes
    O3 C5 C2 . . 119.6(2) yes
    O3 C5 C6 . . 121.0(2) yes
    C2 C5 C6 . . 119.45(19) ?
    C11 C6 C7 . . 119.6(2) ?
    C11 C6 C5 . . 121.3(2) ?
    C7 C6 C5 . . 119.1(2) ?
    C6 C7 C8 . . 120.0(2) ?
    C6 C7 H7 . . 120.0 ?
    C8 C7 H7 . . 120.0 ?
    C9 C8 C7 . . 119.8(3) ?
    C9 C8 H8 . . 120.1 ?
    C7 C8 H8 . . 120.1 ?
    C8 C9 C10 . . 121.3(3) ?
    C8 C9 H9 . . 119.3 ?
    C10 C9 H9 . . 119.3 ?
    C9 C10 C11 . . 118.9(2) ?
    C9 C10 H10 . . 120.6 ?
    C11 C10 H10 . . 120.6 ?
    C6 C11 C10 . . 120.4(2) ?
    C6 C11 H11 . . 119.8 ?
    C10 C11 H11 . . 119.8 ?
    C17A C12 C13B . . 103.0(5) ?
    C13B C12 C17B . . 117.4(6) ?
    C17A C12 C13A . . 120.9(6) ?
    C17B C12 C13A . . 117.7(6) ?
    C17A C12 C3 . . 123.1(6) ?
    C13B C12 C3 . . 124.8(4) ?
    C17B C12 C3 . . 117.0(5) ?
    C13A C12 C3 . . 115.7(3) ?
    C14A C13A C12 . . 118.2(5) ?
    C14A C13A H13A . . 120.9 ?
    C12 C13A H13A . . 120.9 ?
    C15A C14A C13A . . 119.8(6) ?
    C15A C14A H14A . . 120.1 ?
    C13A C14A H14A . . 120.1 ?
    C14A C15A C16A . . 120.7(7) ?
    C14A C15A H15A . . 119.7 ?
    C16A C15A H15A . . 119.7 ?
    C15A C16A C17A . . 120.8(8) ?
    C15A C16A H16A . . 119.6 ?
    C17A C16A H16A . . 119.6 ?
    C12 C17A C16A . . 119.3(9) ?
    C12 C17A H17A . . 120.4 ?
    C16A C17A H17A . . 120.4 ?
    C12 C13B C14B . . 121.0(6) ?
    C12 C13B H13B . . 119.5 ?
    C14B C13B H13B . . 119.5 ?
    C15B C14B C13B . . 119.7(8) ?
    C15B C14B H14B . . 120.1 ?
    C13B C14B H14B . . 120.1 ?
    C14B C15B C16B . . 121.6(8) ?
    C14B C15B H15B . . 119.2 ?
    C16B C15B H15B . . 119.2 ?
    C15B C16B C17B . . 117.3(9) ?
    C15B C16B H16B . . 121.3 ?
    C17B C16B H16B . . 121.3 ?
    C12 C17B C16B . . 122.4(8) ?
    C12 C17B H17B . . 118.8 ?
    C16B C17B H17B . . 118.8 ?
    C19 C18 C23 . . 121.9(2) ?
    C19 C18 N1 . . 120.8(2) ?
    C23 C18 N1 . . 117.3(2) ?
    C18 C19 C20 . . 118.4(3) ?
    C18 C19 H19 . . 120.8 ?
    C20 C19 H19 . . 120.8 ?
    C21 C20 C19 . . 120.7(3) ?
    C21 C20 H20 . . 119.6 ?
    C19 C20 H20 . . 119.6 ?
    C20 C21 C22 . . 120.3(3) ?
    C20 C21 H21 . . 119.8 ?
    C22 C21 H21 . . 119.8 ?
    C21 C22 C23 . . 120.3(3) ?
    C21 C22 H22 . . 119.9 ?
    C23 C22 H22 . . 119.9 ?
    C18 C23 C22 . . 118.3(3) ?
    C18 C23 H23 . . 120.9 ?
    C22 C23 H23 . . 120.9 ?
    O4 C24 H24A . . 109.5 ?
    O4 C24 H24B . . 109.5 ?
    H24A C24 H24B . . 109.5 ?
    O4 C24 H24C . . 109.5 ?
    H24A C24 H24C . . 109.5 ?
    H24B C24 H24C . . 109.5 ?
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
    C3 N1 N2 C1 . . . . 1.6(2) ?
    C18 N1 N2 C1 . . . . 178.68(18) ?
    N1 N2 C1 C2 . . . . -1.3(2) ?
    N1 N2 C1 C4 . . . . -176.51(17) ?
    N2 C1 C2 C3 . . . . 0.6(2) ?
    C4 C1 C2 C3 . . . . 175.28(19) ?
    N2 C1 C2 C5 . . . . -176.6(2) ?
    C4 C1 C2 C5 . . . . -1.8(4) yes
    N2 N1 C3 C2 . . . . -1.3(2) ?
    C18 N1 C3 C2 . . . . -177.9(2) ?
    N2 N1 C3 C12 . . . . -179.42(19) ?
    C18 N1 C3 C12 . . . . 4.0(4) yes
    C1 C2 C3 N1 . . . . 0.4(2) ?
    C5 C2 C3 N1 . . . . 177.7(2) ?
    C1 C2 C3 C12 . . . . 178.4(2) ?
    C5 C2 C3 C12 . . . . -4.3(4) yes
    N2 C1 C4 O1 . . . . 169.3(2) ?
    C2 C1 C4 O1 . . . . -5.1(4) ?
    N2 C1 C4 O2A . . . . -18.0(9) ?
    C2 C1 C4 O2A . . . . 167.6(9) ?
    N2 C1 C4 O2B . . . . -1.4(11) ?
    C2 C1 C4 O2B . . . . -175.8(10) ?
    C3 C2 C5 O3 . . . . -56.6(3) ?
    C1 C2 C5 O3 . . . . 119.9(2) ?
    C3 C2 C5 C6 . . . . 122.6(2) ?
    C1 C2 C5 C6 . . . . -60.8(3) ?
    O3 C5 C6 C11 . . . . 159.9(2) ?
    C2 C5 C6 C11 . . . . -19.4(3) ?
    O3 C5 C6 C7 . . . . -19.5(3) ?
    C2 C5 C6 C7 . . . . 161.29(19) ?
    C11 C6 C7 C8 . . . . 0.2(3) ?
    C5 C6 C7 C8 . . . . 179.5(2) ?
    C6 C7 C8 C9 . . . . -1.0(4) ?
    C7 C8 C9 C10 . . . . 0.2(4) ?
    C8 C9 C10 C11 . . . . 1.4(4) ?
    C7 C6 C11 C10 . . . . 1.4(3) ?
    C5 C6 C11 C10 . . . . -177.90(19) ?
    C9 C10 C11 C6 . . . . -2.2(3) ?
    N1 C3 C12 C17A . . . . -70.3(7) ?
    C2 C3 C12 C17A . . . . 112.0(7) ?
    N1 C3 C12 C13B . . . . 71.2(8) ?
    C2 C3 C12 C13B . . . . -106.5(8) ?
    N1 C3 C12 C17B . . . . -98.5(6) ?
    C2 C3 C12 C17B . . . . 83.9(6) ?
    N1 C3 C12 C13A . . . . 116.2(5) ?
    C2 C3 C12 C13A . . . . -61.5(5) ?
    C17A C12 C13A C14A . . . . 6.4(8) ?
    C13B C12 C13A C14A . . . . -65.5(7) ?
    C17B C12 C13A C14A . . . . 35.0(7) ?
    C3 C12 C13A C14A . . . . -179.9(4) ?
    C12 C13A C14A C15A . . . . -2.9(11) ?
    C13A C14A C15A C16A . . . . -1.0(18) ?
    C14A C15A C16A C17A . . . . 2(2) ?
    C13B C12 C17A C16A . . . . 32.7(10) ?
    C17B C12 C17A C16A . . . . -96(2) ?
    C13A C12 C17A C16A . . . . -5.8(11) ?
    C3 C12 C17A C16A . . . . -178.9(7) ?
    C15A C16A C17A C12 . . . . 1.7(17) ?
    C17A C12 C13B C14B . . . . -28.6(9) ?
    C17B C12 C13B C14B . . . . -6.6(9) ?
    C13A C12 C13B C14B . . . . 94.5(10) ?
    C3 C12 C13B C14B . . . . -176.2(5) ?
    C12 C13B C14B C15B . . . . 5.0(13) ?
    C13B C14B C15B C16B . . . . -4(2) ?
    C14B C15B C16B C17B . . . . 5(2) ?
    C17A C12 C17B C16B . . . . 67(2) ?
    C13B C12 C17B C16B . . . . 7.6(12) ?
    C13A C12 C17B C16B . . . . -37.3(11) ?
    C3 C12 C17B C16B . . . . 178.1(8) ?
    C15B C16B C17B C12 . . . . -6.6(18) ?
    C3 N1 C18 C19 . . . . -68.8(3) ?
    N2 N1 C18 C19 . . . . 114.7(2) ?
    C3 N1 C18 C23 . . . . 111.2(3) ?
    N2 N1 C18 C23 . . . . -65.3(2) ?
    C23 C18 C19 C20 . . . . 1.8(3) ?
    N1 C18 C19 C20 . . . . -178.2(2) ?
    C18 C19 C20 C21 . . . . -0.8(4) ?
    C19 C20 C21 C22 . . . . 0.0(5) ?
    C20 C21 C22 C23 . . . . -0.1(4) ?
    C19 C18 C23 C22 . . . . -1.9(4) ?
    N1 C18 C23 C22 . . . . 178.1(2) ?
    C21 C22 C23 C18 . . . . 1.0(4) ?
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
    O4 H4 N2 5_655 0.82 1.99 2.804(2) 175.9
    O2B H2B O4 . 0.82 1.77 2.583(10) 170.5
    O2A H2A O4 . 0.82 1.77 2.576(8) 165.2
    C10 H10 O1 8_665 0.93 2.46 3.339(3) 158.1
    C14A H14A O4 2_655 0.93 2.53 3.334(6) 145.4
data_global
_journal_date_recd_electronic     2004-12-20
_journal_date_accepted     2004-12-24
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2005
_journal_volume     61
_journal_issue      2
_journal_page_first     o256
_journal_page_last     o258
_journal_paper_category     EO
_publ_contact_author
;
      Namık Özdemir
      Ondokuz Mayıs University
      Arts and Sciences Faculty
      Department of Physics
      55139 Samsun
      Turkey
;
_publ_contact_author_email     namiko@omu.edu.tr
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
4-Benzoyl-1,5-diphenyl-1H-pyrazole-3-carboxylic acid methanol solvate
;
loop_
    _publ_author_name
    _publ_author_address
    'Yıldırım, İsmail'
;    Erciyes University
     Arts and Sciences Faculty
     Department of Chemistry
     38039 Kayseri
     Turkey
;
    'Özdemir, Namık'
;    Ondokuz Mayıs University
     Arts and Sciences Faculty
     Department of Physics
     55139 Samsun
     Turkey
;
    'Akçamur, Yunus'
;    Erciyes University
     Arts and Sciences Faculty
     Department of Chemistry
     38039 Kayseri
     Turkey
;
    'Dinçer, Muharrem'
;    Ondokuz Mayıs University
     Arts and Sciences Faculty
     Department of Physics
     55139 Samsun
     Turkey
;
    'Andaç, Ömer'
;    Ondokuz Mayıs University
     Arts and Sciences Faculty
     Department of Chemistry
     55139 Samsun
     Turkey
;
