#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/07/2220733.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_2220733
loop_
_publ_author_name
'Ikram, Sumeera'
'Zia ul Haq, Muhammad'
'Badshah, Amir'
'Hasan, Aurangzeb'
'Bolte, Michael'
_publ_section_title
;
 2,2'-(1-Phenyl-1H-pyrazole-3,5-diyl)diphenol
;
_journal_coeditor_code           BX2193
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o364
_journal_paper_doi               10.1107/S1600536809001226
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C21 H16 N2 O2'
_chemical_formula_moiety         'C21 H16 N2 O2'
_chemical_formula_sum            'C21 H16 N2 O2'
_chemical_formula_weight         328.36
_chemical_melting_point          473
_chemical_name_systematic
;
2,2'-(1-Phenyl-1H-pyrazole-3,5-diyl)diphenol
;
_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                 104.294(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7034(8)
_cell_length_b                   11.7407(9)
_cell_length_c                   14.9486(14)
_cell_measurement_reflns_used    10768
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.6
_cell_measurement_theta_min      3.6
_cell_volume                     1650.3(2)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2001)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2001)'
_computing_data_reduction        'X-AREA (Stoe & Cie, 2001)'
_computing_molecular_graphics
'PLATON (Spek, 2003) and XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Stoe IPDSII two-circle'
_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  0.0343
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12165
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_min         3.55
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.46
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.149
_refine_ls_extinction_coef       0.030(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3799
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0386
_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)+(0.0529P)²+0.3119P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1014
_reflns_number_gt                3235
_reflns_number_total             3799
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bx2193.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2220733
_cod_database_fobs_code          2220733
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
N N1 0.72854(9) 0.56525(9) 0.70176(6) 0.0273(2) Uani d . 1 . .
N N2 0.60684(9) 0.61144(9) 0.64778(6) 0.0277(2) Uani d . 1 . .
O O1 0.34395(9) 0.66647(10) 0.57881(6) 0.0434(3) Uani d . 1 . .
H H1 0.428(2) 0.6418(18) 0.6211(13) 0.068(6) Uiso d . 1 . .
O O2 1.07930(9) 0.61561(9) 0.60415(7) 0.0416(2) Uani d . 1 . .
H H2 1.170(2) 0.6300(17) 0.5950(13) 0.073(6) Uiso d . 1 . .
C C3 0.63161(11) 0.62529(9) 0.56362(7) 0.0250(2) Uani d . 1 . .
C C4 0.76965(11) 0.58763(10) 0.56388(7) 0.0267(2) Uani d . 1 . .
H H4 0.8130 0.5885 0.5134 0.032 Uiso calc R 1 . .
C C5 0.82919(11) 0.54909(9) 0.65248(7) 0.0260(2) Uani d . 1 . .
C C11 0.73784(12) 0.55181(10) 0.79885(7) 0.0293(2) Uani d . 1 . .
C C12 0.84714(13) 0.60411(11) 0.86344(8) 0.0354(3) Uani d . 1 . .
H H12 0.9170 0.6479 0.8442 0.042 Uiso calc R 1 . .
C C13 0.85265(15) 0.59125(13) 0.95705(9) 0.0447(3) Uani d . 1 . .
H H13 0.9274 0.6257 1.0021 0.054 Uiso calc R 1 . .
C C14 0.74906(17) 0.52810(14) 0.98457(9) 0.0479(4) Uani d . 1 . .
H H14 0.7532 0.5197 1.0484 0.057 Uiso calc R 1 . .
C C15 0.63982(16) 0.47744(13) 0.91924(9) 0.0437(3) Uani d . 1 . .
H H15 0.5689 0.4349 0.9384 0.052 Uiso calc R 1 . .
C C16 0.63368(13) 0.48862(11) 0.82558(8) 0.0349(3) Uani d . 1 . .
H H16 0.5593 0.4535 0.7806 0.042 Uiso calc R 1 . .
C C31 0.51991(11) 0.67507(9) 0.48859(7) 0.0260(2) Uani d . 1 . .
C C32 0.38098(12) 0.69291(11) 0.49811(8) 0.0308(2) Uani d . 1 . .
C C33 0.27648(13) 0.73925(12) 0.42651(9) 0.0399(3) Uani d . 1 . .
H H33 0.1826 0.7492 0.4336 0.048 Uiso calc R 1 . .
C C34 0.30899(14) 0.77093(12) 0.34478(9) 0.0409(3) Uani d . 1 . .
H H34 0.2378 0.8035 0.2962 0.049 Uiso calc R 1 . .
C C35 0.44618(15) 0.75502(12) 0.33381(8) 0.0395(3) Uani d . 1 . .
H H35 0.4687 0.7765 0.2778 0.047 Uiso calc R 1 . .
C C36 0.54978(13) 0.70771(11) 0.40505(8) 0.0329(3) Uani d . 1 . .
H H36 0.6431 0.6972 0.3971 0.040 Uiso calc R 1 . .
C C51 0.96705(11) 0.49298(10) 0.69189(7) 0.0270(2) Uani d . 1 . .
C C52 1.08989(12) 0.52664(10) 0.66442(8) 0.0304(2) Uani d . 1 . .
C C53 1.21876(13) 0.46994(11) 0.69982(9) 0.0368(3) Uani d . 1 . .
H H53 1.3013 0.4927 0.6811 0.044 Uiso calc R 1 . .
C C54 1.22731(13) 0.38090(11) 0.76202(9) 0.0385(3) Uani d . 1 . .
H H54 1.3155 0.3433 0.7856 0.046 Uiso calc R 1 . .
C C55 1.10706(14) 0.34660(11) 0.78991(8) 0.0364(3) Uani d . 1 . .
H H55 1.1127 0.2858 0.8326 0.044 Uiso calc R 1 . .
C C56 0.97871(13) 0.40228(10) 0.75474(8) 0.0317(3) Uani d . 1 . .
H H56 0.8967 0.3784 0.7737 0.038 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
N2 N1 C5 . . 111.28(8) ?
N2 N1 C11 . . 117.92(8) ?
C5 N1 C11 . . 130.48(9) ?
C3 N2 N1 . . 105.77(8) ?
C32 O1 H1 . . 106.6(11) ?
C52 O2 H2 . . 108.2(12) ?
N2 C3 C4 . . 110.36(9) ?
N2 C3 C31 . . 119.40(9) ?
C4 C3 C31 . . 130.24(9) ?
C5 C4 C3 . . 106.08(9) ?
C5 C4 H4 . . 127.0 ?
C3 C4 H4 . . 127.0 ?
N1 C5 C4 . . 106.50(9) ?
N1 C5 C51 . . 122.78(9) ?
C4 C5 C51 . . 130.59(9) ?
C12 C11 C16 . . 121.40(11) ?
C12 C11 N1 . . 119.95(10) ?
C16 C11 N1 . . 118.63(10) ?
C11 C12 C13 . . 118.88(12) ?
C11 C12 H12 . . 120.6 ?
C13 C12 H12 . . 120.6 ?
C14 C13 C12 . . 120.19(13) ?
C14 C13 H13 . . 119.9 ?
C12 C13 H13 . . 119.9 ?
C15 C14 C13 . . 120.23(12) ?
C15 C14 H14 . . 119.9 ?
C13 C14 H14 . . 119.9 ?
C14 C15 C16 . . 120.23(13) ?
C14 C15 H15 . . 119.9 ?
C16 C15 H15 . . 119.9 ?
C11 C16 C15 . . 119.06(12) ?
C11 C16 H16 . . 120.5 ?
C15 C16 H16 . . 120.5 ?
C36 C31 C32 . . 117.60(10) ?
C36 C31 C3 . . 120.71(10) ?
C32 C31 C3 . . 121.69(9) ?
O1 C32 C33 . . 117.66(11) ?
O1 C32 C31 . . 121.29(10) ?
C33 C32 C31 . . 121.04(11) ?
C34 C33 C32 . . 120.13(12) ?
C34 C33 H33 . . 119.9 ?
C32 C33 H33 . . 119.9 ?
C33 C34 C35 . . 119.98(11) ?
C33 C34 H34 . . 120.0 ?
C35 C34 H34 . . 120.0 ?
C36 C35 C34 . . 119.72(11) ?
C36 C35 H35 . . 120.1 ?
C34 C35 H35 . . 120.1 ?
C35 C36 C31 . . 121.51(11) ?
C35 C36 H36 . . 119.2 ?
C31 C36 H36 . . 119.2 ?
C56 C51 C52 . . 118.20(10) ?
C56 C51 C5 . . 121.32(10) ?
C52 C51 C5 . . 120.43(10) ?
O2 C52 C53 . . 121.84(10) ?
O2 C52 C51 . . 118.35(10) ?
C53 C52 C51 . . 119.81(11) ?
C54 C53 C52 . . 120.77(11) ?
C54 C53 H53 . . 119.6 ?
C52 C53 H53 . . 119.6 ?
C53 C54 C55 . . 120.18(11) ?
C53 C54 H54 . . 119.9 ?
C55 C54 H54 . . 119.9 ?
C56 C55 C54 . . 119.32(12) ?
C56 C55 H55 . . 120.3 ?
C54 C55 H55 . . 120.3 ?
C55 C56 C51 . . 121.72(11) ?
C55 C56 H56 . . 119.1 ?
C51 C56 H56 . . 119.1 ?
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
N1 N2 . 1.3672(13) ?
N1 C5 . 1.3740(13) ?
N1 C11 . 1.4403(13) ?
N2 C3 . 1.3477(13) ?
O1 C32 . 1.3765(14) ?
O1 H1 . 0.947(19) ?
O2 C52 . 1.3666(15) ?
O2 H2 . 0.94(2) ?
C3 C4 . 1.4097(15) ?
C3 C31 . 1.4744(15) ?
C4 C5 . 1.3838(15) ?
C4 H4 . 0.9500 ?
C5 C51 . 1.4769(15) ?
C11 C12 . 1.3887(17) ?
C11 C16 . 1.3896(16) ?
C12 C13 . 1.3953(17) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.391(2) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.386(2) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.3928(17) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
C31 C36 . 1.4033(15) ?
C31 C32 . 1.4057(15) ?
C32 C33 . 1.3907(17) ?
C33 C34 . 1.3859(18) ?
C33 H33 . 0.9500 ?
C34 C35 . 1.3935(19) ?
C34 H34 . 0.9500 ?
C35 C36 . 1.3873(17) ?
C35 H35 . 0.9500 ?
C36 H36 . 0.9500 ?
C51 C56 . 1.4060(16) ?
C51 C52 . 1.4098(15) ?
C52 C53 . 1.4000(16) ?
C53 C54 . 1.3878(19) ?
C53 H53 . 0.9500 ?
C54 C55 . 1.3921(19) ?
C54 H54 . 0.9500 ?
C55 C56 . 1.3898(17) ?
C55 H55 . 0.9500 ?
C56 H56 . 0.9500 ?
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
O2 H2 O1 1_655 0.94(2) 1.81(2) 2.7524(12) 176.6(19)
O1 H1 N2 . 0.947(19) 1.718(19) 2.5863(12) 150.9(17)
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
C5 N1 N2 C3 . . . . -0.45(12) ?
C11 N1 N2 C3 . . . . 173.77(10) ?
N1 N2 C3 C4 . . . . 0.08(12) ?
N1 N2 C3 C31 . . . . -179.44(9) ?
N2 C3 C4 C5 . . . . 0.30(13) ?
C31 C3 C4 C5 . . . . 179.76(11) ?
N2 N1 C5 C4 . . . . 0.63(13) ?
C11 N1 C5 C4 . . . . -172.65(11) ?
N2 N1 C5 C51 . . . . -175.58(10) ?
C11 N1 C5 C51 . . . . 11.14(19) ?
C3 C4 C5 N1 . . . . -0.55(12) ?
C3 C4 C5 C51 . . . . 175.26(11) ?
N2 N1 C11 C12 . . . . -121.61(12) ?
C5 N1 C11 C12 . . . . 51.30(18) ?
N2 N1 C11 C16 . . . . 56.64(15) ?
C5 N1 C11 C16 . . . . -130.45(13) ?
C16 C11 C12 C13 . . . . 0.84(19) ?
N1 C11 C12 C13 . . . . 179.04(11) ?
C11 C12 C13 C14 . . . . -0.8(2) ?
C12 C13 C14 C15 . . . . 0.1(2) ?
C13 C14 C15 C16 . . . . 0.5(2) ?
C12 C11 C16 C15 . . . . -0.23(18) ?
N1 C11 C16 C15 . . . . -178.46(11) ?
C14 C15 C16 C11 . . . . -0.5(2) ?
N2 C3 C31 C36 . . . . 169.56(11) ?
C4 C3 C31 C36 . . . . -9.85(18) ?
N2 C3 C31 C32 . . . . -9.64(16) ?
C4 C3 C31 C32 . . . . 170.94(11) ?
C36 C31 C32 O1 . . . . -178.03(11) ?
C3 C31 C32 O1 . . . . 1.20(17) ?
C36 C31 C32 C33 . . . . 1.20(18) ?
C3 C31 C32 C33 . . . . -179.57(12) ?
O1 C32 C33 C34 . . . . 177.90(12) ?
C31 C32 C33 C34 . . . . -1.4(2) ?
C32 C33 C34 C35 . . . . 0.8(2) ?
C33 C34 C35 C36 . . . . -0.2(2) ?
C34 C35 C36 C31 . . . . 0.0(2) ?
C32 C31 C36 C35 . . . . -0.55(18) ?
C3 C31 C36 C35 . . . . -179.78(11) ?
N1 C5 C51 C56 . . . . 35.52(16) ?
C4 C5 C51 C56 . . . . -139.69(13) ?
N1 C5 C51 C52 . . . . -146.91(11) ?
C4 C5 C51 C52 . . . . 37.88(18) ?
C56 C51 C52 O2 . . . . -179.27(11) ?
C5 C51 C52 O2 . . . . 3.09(16) ?
C56 C51 C52 C53 . . . . -0.05(17) ?
C5 C51 C52 C53 . . . . -177.69(10) ?
O2 C52 C53 C54 . . . . 179.03(12) ?
C51 C52 C53 C54 . . . . -0.17(18) ?
C52 C53 C54 C55 . . . . 0.14(19) ?
C53 C54 C55 C56 . . . . 0.10(19) ?
C54 C55 C56 C51 . . . . -0.32(18) ?
C52 C51 C56 C55 . . . . 0.29(17) ?
C5 C51 C56 C55 . . . . 177.91(11) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24741574
