#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/65/2226544.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_2226544
loop_
_publ_author_name
'Shahani, Tara'
'Fun, Hoong-Kun'
'Ragavan, R. Venkat'
'Vijayakumar, V.'
'Sarveswari, S.'
_publ_section_title
;
 4-Methyl-5-phenyl-1H-pyrazol-3-ol
;
_journal_coeditor_code           IS2561
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1697
_journal_page_last               o1698
_journal_paper_doi               10.1107/S1600536810022828
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C10 H10 N2 O'
_chemical_formula_moiety         'C10 H10 N2 O'
_chemical_formula_sum            'C10 H10 N2 O'
_chemical_formula_weight         174.20
_chemical_name_systematic
;
4-Methyl-5-phenyl-1H-pyrazol-3-ol
;
_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                 118.9960(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   26.4082(19)
_cell_length_b                   11.0972(8)
_cell_length_c                   14.1245(10)
_cell_measurement_reflns_used    3052
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      27.24
_cell_measurement_theta_min      3.30
_cell_volume                     3620.4(5)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type
;
Bruker APEXII DUO CCD area-detector diffractometer
;
_diffrn_measurement_method       'φ and ω scans'
_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  0.0493
_diffrn_reflns_av_sigmaI/netI    0.0514
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19166
_diffrn_reflns_theta_full        30.04
_diffrn_reflns_theta_max         30.04
_diffrn_reflns_theta_min         2.04
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9929
_exptl_absorpt_correction_T_min  0.9704
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.260
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         5255
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.134
_refine_ls_R_factor_all          0.1139
_refine_ls_R_factor_gt           0.0587
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0985P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1712
_refine_ls_wR_factor_ref         0.2042
_reflns_number_gt                2907
_reflns_number_total             5255
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2561.cif
_cod_data_source_block           I
_cod_original_cell_volume        3620.4(4)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2226544
_cod_database_fobs_code          2226544
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_disorder_assembly
_atom_site_disorder_group
O O1A 0.30484(5) 1.15234(15) 0.48624(10) 0.0513(4) Uani d . 1 . .
H H1OA 0.3021 1.1865 0.5356 0.077 Uiso d R 1 . .
N N1A 0.17011(7) 1.19165(16) 0.26752(12) 0.0419(4) Uani d . 1 . .
N N2A 0.21137(6) 1.22060(17) 0.36985(11) 0.0416(4) Uani d . 1 . .
C C1A 0.09436(9) 1.0463(3) 0.07114(18) 0.0643(7) Uani d . 1 . .
H H1AA 0.0772 1.0599 0.1142 0.077 Uiso calc R 1 . .
C C2A 0.06077(11) 1.0113(3) -0.0353(2) 0.0835(10) Uani d . 1 . .
H H2AA 0.0211 1.0019 -0.0634 0.100 Uiso calc R 1 . .
C C3A 0.08503(12) 0.9902(3) -0.09985(19) 0.0704(8) Uani d . 1 . .
H H3AA 0.0621 0.9665 -0.1715 0.084 Uiso calc R 1 . .
C C4A 0.14342(12) 1.0042(3) -0.05821(19) 0.0676(7) Uani d . 1 . .
H H4AA 0.1603 0.9906 -0.1017 0.081 Uiso calc R 1 . .
C C5A 0.17726(10) 1.0384(3) 0.04793(17) 0.0605(6) Uani d . 1 . .
H H5AA 0.2170 1.0462 0.0758 0.073 Uiso calc R 1 . .
C C6A 0.15335(8) 1.06126(19) 0.11381(14) 0.0412(4) Uani d . 1 . .
C C7A 0.18926(8) 1.10453(19) 0.22525(14) 0.0386(4) Uani d . 1 . .
C C8A 0.24504(8) 1.07398(19) 0.30334(14) 0.0406(4) Uani d . 1 . .
C C9A 0.25656(7) 1.1493(2) 0.39179(14) 0.0404(4) Uani d . 1 . .
C C10A 0.28424(9) 0.9785(2) 0.30003(17) 0.0526(5) Uani d . 1 . .
H H10A 0.2662 0.9409 0.2300 0.079 Uiso calc R 1 . .
H H10B 0.2914 0.9190 0.3545 0.079 Uiso calc R 1 . .
H H10C 0.3202 1.0143 0.3135 0.079 Uiso calc R 1 . .
O O1B -0.05992(5) 0.70768(16) -0.21038(10) 0.0515(4) Uani d . 1 . .
H H1OB -0.0528 0.7049 -0.2616 0.077 Uiso d R 1 . .
N N1B 0.08261(7) 0.69465(18) -0.01528(12) 0.0468(4) Uani d . 1 . .
N N2B 0.04080(6) 0.70277(17) -0.12057(12) 0.0455(4) Uani d . 1 . .
C C1B 0.14424(9) 0.7478(2) 0.21872(16) 0.0564(6) Uani d . 1 . .
H H1BA 0.1524 0.8034 0.1787 0.068 Uiso calc R 1 . .
C C2B 0.17998(11) 0.7390(3) 0.32909(18) 0.0725(8) Uani d . 1 . .
H H2BA 0.2123 0.7887 0.3631 0.087 Uiso calc R 1 . .
C C3B 0.16837(12) 0.6580(3) 0.38904(18) 0.0708(8) Uani d . 1 . .
H H3BA 0.1925 0.6531 0.4635 0.085 Uiso calc R 1 . .
C C4B 0.12108(10) 0.5843(3) 0.33917(17) 0.0630(7) Uani d . 1 . .
H H4BA 0.1134 0.5285 0.3797 0.076 Uiso calc R 1 . .
C C5B 0.08471(9) 0.5923(2) 0.22872(16) 0.0520(5) Uani d . 1 . .
H H5BA 0.0524 0.5426 0.1954 0.062 Uiso calc R 1 . .
C C6B 0.09620(8) 0.67397(19) 0.16757(14) 0.0409(4) Uani d . 1 . .
C C7B 0.05896(8) 0.68061(19) 0.04958(14) 0.0400(4) Uani d . 1 . .
C C8B -0.00068(8) 0.6800(2) -0.01460(14) 0.0411(5) Uani d . 1 . .
C C9B -0.00976(8) 0.69654(19) -0.12047(14) 0.0406(4) Uani d . 1 . .
C C10B -0.04620(9) 0.6615(3) 0.01754(18) 0.0598(6) Uani d . 1 . .
H H10D -0.0283 0.6528 0.0947 0.090 Uiso calc R 1 . .
H H10E -0.0679 0.5901 -0.0167 0.090 Uiso calc R 1 . .
H H10F -0.0717 0.7298 -0.0047 0.090 Uiso calc R 1 . .
H H1NB 0.1235(11) 0.687(3) 0.0001(19) 0.073(8) Uiso d . 1 . .
H H1NA 0.1316(11) 1.224(2) 0.2420(18) 0.064(7) Uiso d . 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
C9A O1A H1OA . . 115.1 ?
C7A N1A N2A . . 111.00(15) ?
C7A N1A H1NA . . 130.4(15) ?
N2A N1A H1NA . . 117.7(14) ?
C9A N2A N1A . . 105.76(15) ?
C2A C1A C6A . . 120.2(2) ?
C2A C1A H1AA . . 119.9 ?
C6A C1A H1AA . . 119.9 ?
C3A C2A C1A . . 120.9(2) ?
C3A C2A H2AA . . 119.5 ?
C1A C2A H2AA . . 119.5 ?
C2A C3A C4A . . 119.3(2) ?
C2A C3A H3AA . . 120.3 ?
C4A C3A H3AA . . 120.3 ?
C3A C4A C5A . . 120.1(2) ?
C3A C4A H4AA . . 119.9 ?
C5A C4A H4AA . . 119.9 ?
C4A C5A C6A . . 121.3(2) ?
C4A C5A H5AA . . 119.4 ?
C6A C5A H5AA . . 119.4 ?
C5A C6A C1A . . 118.19(18) ?
C5A C6A C7A . . 120.97(18) ?
C1A C6A C7A . . 120.81(18) ?
N1A C7A C8A . . 107.63(16) ?
N1A C7A C6A . . 121.31(16) ?
C8A C7A C6A . . 131.04(18) ?
C7A C8A C9A . . 104.45(17) ?
C7A C8A C10A . . 129.14(17) ?
C9A C8A C10A . . 126.32(17) ?
O1A C9A N2A . . 122.24(17) ?
O1A C9A C8A . . 126.60(17) ?
N2A C9A C8A . . 111.16(15) ?
C8A C10A H10A . . 109.5 ?
C8A C10A H10B . . 109.5 ?
H10A C10A H10B . . 109.5 ?
C8A C10A H10C . . 109.5 ?
H10A C10A H10C . . 109.5 ?
H10B C10A H10C . . 109.5 ?
C9B O1B H1OB . . 106.7 ?
C7B N1B N2B . . 110.74(15) ?
C7B N1B H1NB . . 130.8(14) ?
N2B N1B H1NB . . 117.7(14) ?
C9B N2B N1B . . 106.09(15) ?
C2B C1B C6B . . 120.0(2) ?
C2B C1B H1BA . . 120.0 ?
C6B C1B H1BA . . 120.0 ?
C3B C2B C1B . . 120.7(2) ?
C3B C2B H2BA . . 119.7 ?
C1B C2B H2BA . . 119.7 ?
C4B C3B C2B . . 119.8(2) ?
C4B C3B H3BA . . 120.1 ?
C2B C3B H3BA . . 120.1 ?
C3B C4B C5B . . 120.2(2) ?
C3B C4B H4BA . . 119.9 ?
C5B C4B H4BA . . 119.9 ?
C4B C5B C6B . . 120.3(2) ?
C4B C5B H5BA . . 119.9 ?
C6B C5B H5BA . . 119.9 ?
C1B C6B C5B . . 119.03(18) ?
C1B C6B C7B . . 120.16(18) ?
C5B C6B C7B . . 120.79(18) ?
N1B C7B C8B . . 108.12(15) ?
N1B C7B C6B . . 120.11(16) ?
C8B C7B C6B . . 131.71(17) ?
C7B C8B C9B . . 104.41(16) ?
C7B C8B C10B . . 129.08(17) ?
C9B C8B C10B . . 126.47(17) ?
O1B C9B N2B . . 121.95(16) ?
O1B C9B C8B . . 127.43(17) ?
N2B C9B C8B . . 110.60(15) ?
C8B C10B H10D . . 109.5 ?
C8B C10B H10E . . 109.5 ?
H10D C10B H10E . . 109.5 ?
C8B C10B H10F . . 109.5 ?
H10D C10B H10F . . 109.5 ?
H10E C10B H10F . . 109.5 ?
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
O1A C9A . 1.326(2) ?
O1A H1OA . 0.8273 ?
N1A C7A . 1.356(3) ?
N1A N2A . 1.3612(19) ?
N1A H1NA . 0.97(2) ?
N2A C9A . 1.337(2) ?
C1A C2A . 1.380(3) ?
C1A C6A . 1.381(3) ?
C1A H1AA . 0.9300 ?
C2A C3A . 1.365(4) ?
C2A H2AA . 0.9300 ?
C3A C4A . 1.367(4) ?
C3A H3AA . 0.9300 ?
C4A C5A . 1.375(3) ?
C4A H4AA . 0.9300 ?
C5A C6A . 1.378(3) ?
C5A H5AA . 0.9300 ?
C6A C7A . 1.470(2) ?
C7A C8A . 1.388(2) ?
C8A C9A . 1.409(3) ?
C8A C10A . 1.498(3) ?
C10A H10A . 0.9600 ?
C10A H10B . 0.9600 ?
C10A H10C . 0.9600 ?
O1B C9B . 1.323(2) ?
O1B H1OB . 0.8317 ?
N1B C7B . 1.345(2) ?
N1B N2B . 1.359(2) ?
N1B H1NB . 1.00(3) ?
N2B C9B . 1.338(2) ?
C1B C2B . 1.380(3) ?
C1B C6B . 1.384(3) ?
C1B H1BA . 0.9300 ?
C2B C3B . 1.368(4) ?
C2B H2BA . 0.9300 ?
C3B C4B . 1.368(4) ?
C3B H3BA . 0.9300 ?
C4B C5B . 1.383(3) ?
C4B H4BA . 0.9300 ?
C5B C6B . 1.383(3) ?
C5B H5BA . 0.9300 ?
C6B C7B . 1.470(2) ?
C7B C8B . 1.385(2) ?
C8B C9B . 1.407(3) ?
C8B C10B . 1.491(3) ?
C10B H10D . 0.9600 ?
C10B H10E . 0.9600 ?
C10B H10F . 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
O1A H1OA N2A 7_576 0.83 1.85 2.673(2) 171 yes
O1B H1OB N2B 2_554 0.83 1.84 2.670(2) 177 yes
N1B H1NB O1A 4_545 1.00(3) 1.85(3) 2.836(3) 171(3) yes
N1A H1NA O1B 5_575 0.97(3) 1.88(3) 2.844(2) 173(2) yes
C10A H10C Cg1 6_555 0.96 2.77 3.575(3) 142 yes
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
C7A N1A N2A C9A . . . . -0.7(2) ?
C6A C1A C2A C3A . . . . 0.3(5) ?
C1A C2A C3A C4A . . . . 0.0(5) ?
C2A C3A C4A C5A . . . . 0.4(5) ?
C3A C4A C5A C6A . . . . -1.2(4) ?
C4A C5A C6A C1A . . . . 1.4(4) ?
C4A C5A C6A C7A . . . . -176.4(2) ?
C2A C1A C6A C5A . . . . -1.0(4) ?
C2A C1A C6A C7A . . . . 176.8(3) ?
N2A N1A C7A C8A . . . . 0.7(2) ?
N2A N1A C7A C6A . . . . -177.51(17) ?
C5A C6A C7A N1A . . . . 138.9(2) ?
C1A C6A C7A N1A . . . . -38.9(3) ?
C5A C6A C7A C8A . . . . -38.9(3) ?
C1A C6A C7A C8A . . . . 143.3(2) ?
N1A C7A C8A C9A . . . . -0.5(2) ?
C6A C7A C8A C9A . . . . 177.5(2) ?
N1A C7A C8A C10A . . . . 176.4(2) ?
C6A C7A C8A C10A . . . . -5.6(4) ?
N1A N2A C9A O1A . . . . -179.23(17) ?
N1A N2A C9A C8A . . . . 0.4(2) ?
C7A C8A C9A O1A . . . . 179.64(19) ?
C10A C8A C9A O1A . . . . 2.7(3) ?
C7A C8A C9A N2A . . . . 0.1(2) ?
C10A C8A C9A N2A . . . . -176.89(19) ?
C7B N1B N2B C9B . . . . 1.5(2) ?
C6B C1B C2B C3B . . . . -0.2(4) ?
C1B C2B C3B C4B . . . . 0.4(5) ?
C2B C3B C4B C5B . . . . -0.7(4) ?
C3B C4B C5B C6B . . . . 0.8(4) ?
C2B C1B C6B C5B . . . . 0.2(4) ?
C2B C1B C6B C7B . . . . -178.2(2) ?
C4B C5B C6B C1B . . . . -0.5(3) ?
C4B C5B C6B C7B . . . . 178.0(2) ?
N2B N1B C7B C8B . . . . -0.3(2) ?
N2B N1B C7B C6B . . . . -177.91(18) ?
C1B C6B C7B N1B . . . . 39.6(3) ?
C5B C6B C7B N1B . . . . -138.8(2) ?
C1B C6B C7B C8B . . . . -137.3(2) ?
C5B C6B C7B C8B . . . . 44.2(3) ?
N1B C7B C8B C9B . . . . -0.9(2) ?
C6B C7B C8B C9B . . . . 176.3(2) ?
N1B C7B C8B C10B . . . . 177.0(2) ?
C6B C7B C8B C10B . . . . -5.9(4) ?
N1B N2B C9B O1B . . . . 176.63(19) ?
N1B N2B C9B C8B . . . . -2.1(2) ?
C7B C8B C9B O1B . . . . -176.7(2) ?
C10B C8B C9B O1B . . . . 5.3(4) ?
C7B C8B C9B N2B . . . . 1.9(2) ?
C10B C8B C9B N2B . . . . -176.1(2) ?
