#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/44/2204463.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_2204463
loop_
_publ_author_name
'Zhu, Hong-Jun'
'Wang, Dan-Dan'
'Ma, Ji'
_publ_section_title
;
 3-Hydroxy-5-(4-methoxyphenyl)-1-phenyl-1H-pyrazole
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2144
_journal_page_last               o2146
_journal_paper_doi               10.1107/S1600536804026789
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C16 H14 N2 O2'
_chemical_formula_moiety         'C16 H14 N2 O2'
_chemical_formula_sum            'C16 H14 N2 O2'
_chemical_formula_weight         266.29
_chemical_name_systematic
;
5-(4-Methoxyphenyl)-1-phenyl-3-hydroxy-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                88.90(3)
_cell_angle_beta                 86.63(3)
_cell_angle_gamma                70.37(3)
_cell_formula_units_Z            4
_cell_length_a                   9.4266(19)
_cell_length_b                   9.938(2)
_cell_length_c                   15.347(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      24.05
_cell_measurement_theta_min      2.03
_cell_volume                     1351.8(5)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Bruker, 2000)'
_computing_data_reduction        'SHELXTL (Bruker, 2000)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    SHELXTL
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker P4'
_diffrn_measurement_method       2θ/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  0.0115
_diffrn_reflns_av_sigmaI/netI    0.0286
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5322
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.33
_diffrn_standards_decay_%        0.01
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details   '(XPREP in SHELXTL; Bruker, 2000)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.200
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         5322
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0962
_refine_ls_R_factor_gt           0.0531
_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)+(0.06P)²+0.44P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1155
_refine_ls_wR_factor_ref         0.1379
_reflns_number_gt                3789
_reflns_number_total             5322
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci6459.cif
_cod_data_source_block           I
_cod_original_cell_volume        1351.9(5)
_cod_database_code               2204463
_cod_database_fobs_code          2204463
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 0.1190(2) 0.29610(18) 0.49408(11) 0.0570(4) Uani d . 1 O
H1 0.0396 0.3520 0.5151 0.086 Uiso calc R 1 H
O2 0.9594(2) 0.37515(18) 0.23268(11) 0.0576(5) Uani d . 1 O
N1 0.1547(2) 0.5107(2) 0.45785(13) 0.0542(5) Uani d . 1 N
N2 0.2785(2) 0.5424(2) 0.41793(13) 0.0532(5) Uani d . 1 N
C1 0.2037(3) 0.3675(3) 0.46163(17) 0.0546(6) Uani d . 1 C
C2 0.3453(3) 0.3038(3) 0.42142(16) 0.0549(6) Uani d . 1 C
H2 0.3988 0.2071 0.4137 0.066 Uiso calc R 1 H
C3 0.3891(3) 0.4228(3) 0.39484(17) 0.0544(6) Uani d . 1 C
C4 0.5379(3) 0.4224(3) 0.35122(17) 0.0555(6) Uani d . 1 C
C5 0.6045(3) 0.5207(3) 0.36527(17) 0.0558(6) Uani d . 1 C
H5 0.5552 0.5976 0.4020 0.067 Uiso calc R 1 H
C6 0.7446(3) 0.5096(3) 0.32615(17) 0.0564(6) Uani d . 1 C
H6 0.7868 0.5802 0.3346 0.068 Uiso calc R 1 H
C7 0.8177(3) 0.3964(3) 0.27637(17) 0.0568(6) Uani d . 1 C
C8 0.7613(3) 0.2903(3) 0.26193(17) 0.0569(6) Uani d . 1 C
H8 0.8152 0.2124 0.2270 0.068 Uiso calc R 1 H
C9 0.6175(3) 0.3015(3) 0.30180(17) 0.0566(6) Uani d . 1 C
H9 0.5772 0.2290 0.2950 0.068 Uiso calc R 1 H
C10 1.0348(3) 0.4642(3) 0.25523(18) 0.0583(6) Uani d . 1 C
H10A 0.9755 0.5612 0.2429 0.087 Uiso calc R 1 H
H10B 1.1298 0.4394 0.2222 0.087 Uiso calc R 1 H
H10C 1.0521 0.4544 0.3164 0.087 Uiso calc R 1 H
C11 0.2482(3) 0.6880(3) 0.39407(16) 0.0493(6) Uani d . 1 C
C12 0.2499(3) 0.7253(3) 0.30674(16) 0.0526(6) Uani d . 1 C
H12 0.2730 0.6549 0.2640 0.063 Uiso calc R 1 H
C13 0.2169(3) 0.8691(3) 0.28257(18) 0.0551(6) Uani d . 1 C
H13 0.2198 0.8949 0.2241 0.066 Uiso calc R 1 H
C14 0.1807(3) 0.9688(3) 0.34594(17) 0.0558(6) Uani d . 1 C
H14 0.1569 1.0644 0.3302 0.067 Uiso calc R 1 H
C15 0.1778(3) 0.9343(3) 0.43357(17) 0.0553(6) Uani d . 1 C
H15 0.1539 1.0052 0.4760 0.066 Uiso calc R 1 H
C16 0.2110(3) 0.7924(3) 0.45693(17) 0.0532(6) Uani d . 1 C
H16 0.2080 0.7676 0.5156 0.064 Uiso calc R 1 H
O1A 0.9535(2) 0.94177(18) -0.10783(11) 0.0565(4) Uani d . 1 O
H1A 1.0028 0.9820 -0.0831 0.085 Uiso calc R 1 H
O2A 0.26504(19) 0.55211(18) 0.09247(11) 0.0564(4) Uani d . 1 O
N1A 0.8693(2) 0.9293(2) 0.03676(14) 0.0542(5) Uani d . 1 N
N2A 0.7633(2) 0.8763(2) 0.07750(13) 0.0538(5) Uani d . 1 N
C1A 0.8623(3) 0.9031(3) -0.04811(17) 0.0548(6) Uani d . 1 C
C2A 0.7638(3) 0.8341(3) -0.06357(17) 0.0548(6) Uani d . 1 C
H2A 0.7465 0.8019 -0.1171 0.066 Uiso calc R 1 H
C3A 0.6940(3) 0.8214(3) 0.01698(17) 0.0542(6) Uani d . 1 C
C4A 0.5826(3) 0.7490(3) 0.03654(17) 0.0545(6) Uani d . 1 C
C5A 0.4553(3) 0.7820(3) -0.01006(17) 0.0546(6) Uani d . 1 C
H5A 0.4416 0.8502 -0.0540 0.066 Uiso calc R 1 H
C6A 0.3467(3) 0.7181(3) 0.00557(17) 0.0553(6) Uani d . 1 C
H6A 0.2620 0.7415 -0.0274 0.066 Uiso calc R 1 H
C7A 0.3683(3) 0.6179(3) 0.07191(17) 0.0558(6) Uani d . 1 C
C8A 0.4898(3) 0.5880(3) 0.12016(17) 0.0557(6) Uani d . 1 C
H8A 0.5014 0.5214 0.1649 0.067 Uiso calc R 1 H
C9A 0.5965(3) 0.6520(3) 0.10583(17) 0.0551(6) Uani d . 1 C
H9A 0.6775 0.6315 0.1416 0.066 Uiso calc R 1 H
C10A 0.1389(3) 0.5796(3) 0.03929(17) 0.0562(6) Uani d . 1 C
H10D 0.0769 0.5254 0.0606 0.084 Uiso calc R 1 H
H10E 0.1741 0.5524 -0.0199 0.084 Uiso calc R 1 H
H10F 0.0809 0.6796 0.0414 0.084 Uiso calc R 1 H
C11A 0.7359(3) 0.8895(3) 0.16712(17) 0.0545(6) Uani d . 1 C
C12A 0.5876(3) 0.9299(3) 0.20412(17) 0.0548(6) Uani d . 1 C
H12A 0.5061 0.9509 0.1688 0.066 Uiso calc R 1 H
C13A 0.5645(3) 0.9381(3) 0.29568(17) 0.0553(6) Uani d . 1 C
H13A 0.4674 0.9622 0.3213 0.066 Uiso calc R 1 H
C14A 0.6868(3) 0.9101(3) 0.34766(18) 0.0554(6) Uani d . 1 C
H14A 0.6714 0.9116 0.4081 0.066 Uiso calc R 1 H
C15A 0.8288(3) 0.8806(3) 0.31110(17) 0.0554(6) Uani d . 1 C
H15A 0.9093 0.8687 0.3462 0.066 Uiso calc R 1 H
C16A 0.8531(3) 0.8683(3) 0.22081(17) 0.0548(6) Uani d . 1 C
H16A 0.9509 0.8451 0.1963 0.066 Uiso calc R 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
C1 O1 H1 109.5 ?
C10 O2 C7 116.6(2) yes
C1 N1 N2 103.7(2) yes
C3 N2 N1 110.4(2) yes
C3 N2 C11 132.8(2) ?
N1 N2 C11 115.0(2) ?
O1 C1 N1 122.3(2) ?
O1 C1 C2 123.6(2) yes
N1 C1 C2 113.8(2) ?
C1 C2 C3 102.9(2) yes
C1 C2 H2 128.5 ?
C3 C2 H2 128.5 ?
N2 C3 C2 109.0(2) ?
N2 C3 C4 122.7(2) ?
C2 C3 C4 128.3(2) ?
C5 C4 C9 118.9(2) ?
C5 C4 C3 124.8(2) ?
C9 C4 C3 115.8(2) ?
C4 C5 C6 121.6(3) ?
C4 C5 H5 119.2 ?
C6 C5 H5 119.2 ?
C7 C6 C5 119.1(3) ?
C7 C6 H6 120.5 ?
C5 C6 H6 120.5 ?
C6 C7 C8 122.9(3) ?
C6 C7 O2 123.8(2) ?
C8 C7 O2 113.3(2) ?
C7 C8 C9 118.2(2) ?
C7 C8 H8 120.9 ?
C9 C8 H8 120.9 ?
C4 C9 C8 119.1(2) ?
C4 C9 H9 120.4 ?
C8 C9 H9 120.4 ?
O2 C10 H10A 109.5 ?
O2 C10 H10B 109.5 ?
H10A C10 H10B 109.5 ?
O2 C10 H10C 109.5 ?
H10A C10 H10C 109.5 ?
H10B C10 H10C 109.5 ?
C16 C11 C12 119.8(2) ?
C16 C11 N2 120.4(2) ?
C12 C11 N2 119.7(2) ?
C11 C12 C13 120.1(2) ?
C11 C12 H12 119.9 ?
C13 C12 H12 119.9 ?
C14 C13 C12 118.5(2) ?
C14 C13 H13 120.7 ?
C12 C13 H13 120.7 ?
C13 C14 C15 122.4(3) ?
C13 C14 H14 118.8 ?
C15 C14 H14 118.8 ?
C14 C15 C16 118.7(2) ?
C14 C15 H15 120.6 ?
C16 C15 H15 120.6 ?
C11 C16 C15 120.4(2) ?
C11 C16 H16 119.8 ?
C15 C16 H16 119.8 ?
C1A O1A H1A 109.5 ?
C7A O2A C10A 118.5(2) ?
C1A N1A N2A 103.3(2) ?
C3A N2A C11A 129.4(2) ?
C3A N2A N1A 111.0(2) ?
C11A N2A N1A 119.5(2) ?
N1A C1A O1A 119.1(2) ?
N1A C1A C2A 113.7(2) ?
O1A C1A C2A 127.1(2) ?
C1A C2A C3A 106.0(2) ?
C1A C2A H2A 127.0 ?
C3A C2A H2A 127.0 ?
N2A C3A C2A 105.8(2) ?
N2A C3A C4A 126.2(2) ?
C2A C3A C4A 127.6(2) ?
C5A C4A C9A 117.5(2) ?
C5A C4A C3A 120.2(2) ?
C9A C4A C3A 122.1(2) ?
C4A C5A C6A 122.8(3) ?
C4A C5A H5A 118.6 ?
C6A C5A H5A 118.6 ?
C5A C6A C7A 117.8(3) ?
C5A C6A H6A 121.1 ?
C7A C6A H6A 121.1 ?
C8A C7A O2A 118.4(2) ?
C8A C7A C6A 120.2(3) ?
O2A C7A C6A 121.3(2) ?
C7A C8A C9A 122.4(3) ?
C7A C8A H8A 118.8 ?
C9A C8A H8A 118.8 ?
C8A C9A C4A 119.2(3) ?
C8A C9A H9A 120.4 ?
C4A C9A H9A 120.4 ?
O2A C10A H10D 109.5 ?
O2A C10A H10E 109.5 ?
H10D C10A H10E 109.5 ?
O2A C10A H10F 109.5 ?
H10D C10A H10F 109.5 ?
H10E C10A H10F 109.5 ?
C16A C11A N2A 120.4(2) ?
C16A C11A C12A 119.1(2) ?
N2A C11A C12A 120.5(2) ?
C11A C12A C13A 118.8(2) ?
C11A C12A H12A 120.6 ?
C13A C12A H12A 120.6 ?
C14A C13A C12A 120.0(2) ?
C14A C13A H13A 120.0 ?
C12A C13A H13A 120.0 ?
C15A C14A C13A 120.6(3) ?
C15A C14A H14A 119.7 ?
C13A C14A H14A 119.7 ?
C14A C15A C16A 119.6(3) ?
C14A C15A H15A 120.2 ?
C16A C15A H15A 120.2 ?
C11A C16A C15A 121.5(2) ?
C11A C16A H16A 119.2 ?
C15A C16A H16A 119.2 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 1.307(3) yes
O1 H1 0.82 ?
O2 C10 1.368(3) yes
O2 C7 1.410(3) yes
N1 C1 1.341(3) ?
N1 N2 1.411(3) yes
N2 C3 1.328(3) yes
N2 C11 1.423(3) ?
C1 C2 1.384(4) yes
C2 C3 1.423(3) yes
C2 H2 0.93 ?
C3 C4 1.517(4) ?
C4 C5 1.353(4) ?
C4 C9 1.395(4) ?
C5 C6 1.388(4) ?
C5 H5 0.93 ?
C6 C7 1.332(4) ?
C6 H6 0.93 ?
C7 C8 1.357(4) ?
C8 C9 1.425(4) ?
C8 H8 0.93 ?
C9 H9 0.93 ?
C10 H10A 0.96 ?
C10 H10B 0.96 ?
C10 H10C 0.96 ?
C11 C16 1.373(3) ?
C11 C12 1.384(3) ?
C12 C13 1.404(4) ?
C12 H12 0.93 ?
C13 C14 1.348(4) ?
C13 H13 0.93 ?
C14 C15 1.383(4) ?
C14 H14 0.93 ?
C15 C16 1.383(4) ?
C15 H15 0.93 ?
C16 H16 0.93 ?
O1A C1A 1.358(3) ?
O1A H1A 0.82 ?
O2A C7A 1.363(3) ?
O2A C10A 1.429(3) ?
N1A C1A 1.343(3) ?
N1A N2A 1.391(3) ?
N2A C3A 1.385(3) ?
N2A C11A 1.385(3) ?
C1A C2A 1.360(4) ?
C2A C3A 1.389(3) ?
C2A H2A 0.93 ?
C3A C4A 1.474(4) ?
C4A C5A 1.374(4) ?
C4A C9A 1.403(4) ?
C5A C6A 1.383(4) ?
C5A H5A 0.93 ?
C6A C7A 1.385(4) ?
C6A H6A 0.93 ?
C7A C8A 1.346(4) ?
C8A C9A 1.365(4) ?
C8A H8A 0.93 ?
C9A H9A 0.93 ?
C10A H10D 0.96 ?
C10A H10E 0.96 ?
C10A H10F 0.96 ?
C11A C16A 1.374(4) ?
C11A C12A 1.406(4) ?
C12A C13A 1.409(4) ?
C12A H12A 0.93 ?
C13A C14A 1.388(4) ?
C13A H13A 0.93 ?
C14A C15A 1.359(4) ?
C14A H14A 0.93 ?
C15A C16A 1.392(4) ?
C15A H15A 0.93 ?
C16A H16A 0.93 ?
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 H1 N1 2_566 0.82 1.91 2.718(3) 169 yes
O1A H1A N1A 2_775 0.82 1.89 2.707(3) 174 yes
C10 H10C N1 1_655 0.96 2.57 3.461(4) 154 yes
C10A H10F N1A 1_455 0.96 2.61 3.551(3) 166 yes
C5 H5 Cg1 2_666 0.93 3.07 3.495(3) 110 yes
C5A H5A Cg2 2_675 0.93 2.97 3.434(3) 113 yes
C8A H8A Cg3 1_555 0.93 2.91 3.682(3) 142 yes
C10 H10C Cg1 1_665 0.96 2.76 3.553(3) 141 yes
C10A H10F Cg2 1_455 0.96 2.85 3.646(3) 141 yes
C15A H15A Cg4 1_655 0.93 2.81 3.660(3) 152 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24733360
