#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/88/2228885.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_2228885
loop_
_publ_author_name
'Loh, Wan-Sin'
'Fun, Hoong-Kun'
'Ragavan, R. Venkat'
'Vijayakumar, V.'
'Sarveswari, S.'
_publ_section_title
;
 4-Methyl-5-phenyl-1H-pyrazol-3(2H)-one
;
_journal_coeditor_code           SJ5074
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o151
_journal_page_last               o152
_journal_paper_doi               10.1107/S160053681005213X
_journal_volume                  67
_journal_year                    2011
_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(2H)-one
;
_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                 118.9610(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   25.9337(4)
_cell_length_b                   10.81000(10)
_cell_length_c                   14.1426(2)
_cell_measurement_reflns_used    9946
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      30.06
_cell_measurement_theta_min      2.37
_cell_volume                     3468.99(9)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector
;
_diffrn_measurement_method       'φ and 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  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0234
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            36992
_diffrn_reflns_theta_full        30.09
_diffrn_reflns_theta_max         30.09
_diffrn_reflns_theta_min         1.79
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.9780
_exptl_absorpt_correction_T_min  0.9610
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.221
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         5087
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0438
_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)+(0.0684P)²+2.0500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1186
_reflns_number_gt                4389
_reflns_number_total             5087
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj5074.cif
_cod_data_source_block           I
_cod_original_cell_volume        3468.98(8)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2228885
_cod_database_fobs_code          2228885
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 0.19371(3) 0.15583(7) 0.01430(6) 0.01628(16) Uani d . 1 . .
N N1A 0.33170(4) 0.19356(8) 0.23566(7) 0.01429(17) Uani d . 1 . .
N N2A 0.28884(4) 0.22212(8) 0.13372(7) 0.01378(17) Uani d . 1 . .
C C1A 0.40804(5) 0.05241(11) 0.43463(9) 0.0198(2) Uani d . 1 . .
H H1AA 0.4262 0.0681 0.3931 0.024 Uiso calc R 1 . .
C C2A 0.44188(5) 0.02010(12) 0.54257(10) 0.0249(2) Uani d . 1 . .
H H2AA 0.4826 0.0147 0.5730 0.030 Uiso calc R 1 . .
C C3A 0.41532(5) -0.00418(11) 0.60540(10) 0.0222(2) Uani d . 1 . .
H H3AA 0.4382 -0.0251 0.6779 0.027 Uiso calc R 1 . .
C C4A 0.35439(5) 0.00296(10) 0.55947(9) 0.0209(2) Uani d . 1 . .
H H4AA 0.3364 -0.0139 0.6012 0.025 Uiso calc R 1 . .
C C5A 0.32019(5) 0.03512(10) 0.45141(9) 0.0188(2) Uani d . 1 . .
H H5AA 0.2794 0.0391 0.4211 0.023 Uiso calc R 1 . .
C C6A 0.34665(4) 0.06155(9) 0.38784(8) 0.01417(19) Uani d . 1 . .
C C7A 0.31075(4) 0.10488(9) 0.27595(8) 0.01305(19) Uani d . 1 . .
C C8A 0.25384(4) 0.07360(9) 0.19815(8) 0.01399(19) Uani d . 1 . .
C C9A 0.24055(4) 0.14984(9) 0.10712(8) 0.01324(19) Uani d . 1 . .
C C10A 0.21385(4) -0.02449(10) 0.20107(9) 0.0171(2) Uani d . 1 . .
H H10A 0.2367 -0.0958 0.2385 0.026 Uiso calc R 1 . .
H H10B 0.1855 -0.0472 0.1286 0.026 Uiso calc R 1 . .
H H10C 0.1937 0.0066 0.2380 0.026 Uiso calc R 1 . .
O O1B 0.43937(3) 0.28341(7) 0.28820(6) 0.01641(16) Uani d . 1 . .
N N1B 0.58492(4) 0.29961(8) 0.48713(7) 0.01537(18) Uani d . 1 . .
N N2B 0.54157(4) 0.29083(8) 0.38216(7) 0.01525(18) Uani d . 1 . .
C C1B 0.64581(5) 0.25037(10) 0.72121(9) 0.0177(2) Uani d . 1 . .
H H1BA 0.6549 0.1929 0.6825 0.021 Uiso calc R 1 . .
C C2B 0.68154(5) 0.26106(11) 0.83201(9) 0.0225(2) Uani d . 1 . .
H H2BA 0.7144 0.2102 0.8676 0.027 Uiso calc R 1 . .
C C3B 0.66848(5) 0.34762(12) 0.89026(10) 0.0233(2) Uani d . 1 . .
H H3BA 0.6926 0.3549 0.9645 0.028 Uiso calc R 1 . .
C C4B 0.61925(5) 0.42316(11) 0.83712(9) 0.0208(2) Uani d . 1 . .
H H4BA 0.6107 0.4816 0.8758 0.025 Uiso calc R 1 . .
C C5B 0.58278(5) 0.41160(10) 0.72656(9) 0.0168(2) Uani d . 1 . .
H H5BA 0.5494 0.4610 0.6916 0.020 Uiso calc R 1 . .
C C6B 0.59605(4) 0.32598(9) 0.66741(8) 0.01363(19) Uani d . 1 . .
C C7B 0.55927(4) 0.31664(9) 0.54975(8) 0.01354(19) Uani d . 1 . .
C C8B 0.49830(4) 0.31808(9) 0.48467(8) 0.01383(19) Uani d . 1 . .
C C9B 0.48786(4) 0.29746(9) 0.37751(8) 0.01359(19) Uani d . 1 . .
C C10B 0.45201(4) 0.34052(10) 0.51676(9) 0.0184(2) Uani d . 1 . .
H H10D 0.4627 0.2991 0.5838 0.028 Uiso calc R 1 . .
H H10E 0.4149 0.3091 0.4617 0.028 Uiso calc R 1 . .
H H10F 0.4487 0.4277 0.5254 0.028 Uiso calc R 1 . .
H H1NB 0.6234(7) 0.3100(16) 0.5038(13) 0.034(4) Uiso d . 1 . .
H H1NA 0.3696(7) 0.2271(15) 0.2649(13) 0.030(4) Uiso d . 1 . .
H H2NA 0.2954(8) 0.2691(17) 0.0857(14) 0.042(5) Uiso d . 1 . .
H H2NB 0.5490(7) 0.2858(15) 0.3239(13) 0.032(4) 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
C7A N1A N2A . . 108.49(8) ?
C7A N1A H1NA . . 129.6(10) ?
N2A N1A H1NA . . 121.6(10) ?
N1A N2A C9A . . 109.34(8) ?
N1A N2A H2NA . . 123.7(11) ?
C9A N2A H2NA . . 125.5(11) ?
C2A C1A C6A . . 120.42(10) ?
C2A C1A H1AA . . 119.8 ?
C6A C1A H1AA . . 119.8 ?
C1A C2A C3A . . 120.42(10) ?
C1A C2A H2AA . . 119.8 ?
C3A C2A H2AA . . 119.8 ?
C2A C3A C4A . . 119.66(11) ?
C2A C3A H3AA . . 120.2 ?
C4A C3A H3AA . . 120.2 ?
C5A C4A C3A . . 120.25(10) ?
C5A C4A H4AA . . 119.9 ?
C3A C4A H4AA . . 119.9 ?
C4A C5A C6A . . 120.49(10) ?
C4A C5A H5AA . . 119.8 ?
C6A C5A H5AA . . 119.8 ?
C5A C6A C1A . . 118.74(10) ?
C5A C6A C7A . . 120.29(9) ?
C1A C6A C7A . . 120.89(9) ?
N1A C7A C8A . . 109.11(9) ?
N1A C7A C6A . . 120.23(9) ?
C8A C7A C6A . . 130.60(9) ?
C7A C8A C9A . . 105.93(8) ?
C7A C8A C10A . . 129.40(9) ?
C9A C8A C10A . . 124.56(9) ?
O1A C9A N2A . . 122.59(9) ?
O1A C9A C8A . . 130.31(9) ?
N2A C9A C8A . . 107.10(9) ?
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 ?
C7B N1B N2B . . 108.33(8) ?
C7B N1B H1NB . . 129.5(11) ?
N2B N1B H1NB . . 120.7(11) ?
N1B N2B C9B . . 109.45(9) ?
N1B N2B H2NB . . 123.4(10) ?
C9B N2B H2NB . . 127.0(10) ?
C2B C1B C6B . . 120.09(10) ?
C2B C1B H1BA . . 120.0 ?
C6B C1B H1BA . . 120.0 ?
C1B C2B C3B . . 120.25(10) ?
C1B C2B H2BA . . 119.9 ?
C3B C2B H2BA . . 119.9 ?
C4B C3B C2B . . 119.85(11) ?
C4B C3B H3BA . . 120.1 ?
C2B C3B H3BA . . 120.1 ?
C5B C4B C3B . . 120.20(10) ?
C5B C4B H4BA . . 119.9 ?
C3B C4B H4BA . . 119.9 ?
C4B C5B C6B . . 120.22(10) ?
C4B C5B H5BA . . 119.9 ?
C6B C5B H5BA . . 119.9 ?
C5B C6B C1B . . 119.37(10) ?
C5B C6B C7B . . 120.73(9) ?
C1B C6B C7B . . 119.89(9) ?
N1B C7B C8B . . 109.25(9) ?
N1B C7B C6B . . 119.73(9) ?
C8B C7B C6B . . 130.99(9) ?
C7B C8B C9B . . 105.79(8) ?
C7B C8B C10B . . 128.55(10) ?
C9B C8B C10B . . 125.63(9) ?
O1B C9B N2B . . 121.99(9) ?
O1B C9B C8B . . 130.90(9) ?
N2B C9B C8B . . 107.09(9) ?
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 . 1.2878(12) ?
N1A C7A . 1.3560(13) ?
N1A N2A . 1.3628(12) ?
N1A H1NA . 0.935(16) ?
N2A C9A . 1.3655(12) ?
N2A H2NA . 0.928(19) ?
C1A C2A . 1.3875(16) ?
C1A C6A . 1.4006(14) ?
C1A H1AA . 0.9300 ?
C2A C3A . 1.3878(17) ?
C2A H2AA . 0.9300 ?
C3A C4A . 1.3896(16) ?
C3A H3AA . 0.9300 ?
C4A C5A . 1.3893(16) ?
C4A H4AA . 0.9300 ?
C5A C6A . 1.3994(14) ?
C5A H5AA . 0.9300 ?
C6A C7A . 1.4708(14) ?
C7A C8A . 1.3895(13) ?
C8A C9A . 1.4233(14) ?
C8A C10A . 1.4978(13) ?
C10A H10A . 0.9600 ?
C10A H10B . 0.9600 ?
C10A H10C . 0.9600 ?
O1B C9B . 1.2890(12) ?
N1B C7B . 1.3533(13) ?
N1B N2B . 1.3640(12) ?
N1B H1NB . 0.913(17) ?
N2B C9B . 1.3641(12) ?
N2B H2NB . 0.933(17) ?
C1B C2B . 1.3861(16) ?
C1B C6B . 1.4004(14) ?
C1B H1BA . 0.9300 ?
C2B C3B . 1.3926(17) ?
C2B H2BA . 0.9300 ?
C3B C4B . 1.3901(17) ?
C3B H3BA . 0.9300 ?
C4B C5B . 1.3866(16) ?
C4B H4BA . 0.9300 ?
C5B C6B . 1.3979(14) ?
C5B H5BA . 0.9300 ?
C6B C7B . 1.4668(14) ?
C7B C8B . 1.3920(13) ?
C8B C9B . 1.4221(14) ?
C8B C10B . 1.4946(14) ?
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
N1B H1NB O1A 8_556 0.913(17) 1.796(17) 2.7001(11) 170.0(16) yes
N1A H1NA O1B . 0.935(19) 1.78(2) 2.6987(14) 165.9(16) yes
N2A H2NA O1A 7_555 0.93(2) 1.768(19) 2.6917(12) 173.9(17) yes
N2B H2NB O1B 2_655 0.934(18) 1.752(18) 2.6850(13) 177.0(16) 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 . . . . -1.33(11) ?
C6A C1A C2A C3A . . . . 0.33(18) ?
C1A C2A C3A C4A . . . . 0.55(19) ?
C2A C3A C4A C5A . . . . -0.48(18) ?
C3A C4A C5A C6A . . . . -0.47(17) ?
C4A C5A C6A C1A . . . . 1.33(16) ?
C4A C5A C6A C7A . . . . -175.25(10) ?
C2A C1A C6A C5A . . . . -1.26(16) ?
C2A C1A C6A C7A . . . . 175.29(10) ?
N2A N1A C7A C8A . . . . 1.22(11) ?
N2A N1A C7A C6A . . . . -176.28(8) ?
C5A C6A C7A N1A . . . . 141.18(10) ?
C1A C6A C7A N1A . . . . -35.32(14) ?
C5A C6A C7A C8A . . . . -35.71(16) ?
C1A C6A C7A C8A . . . . 147.80(11) ?
N1A C7A C8A C9A . . . . -0.64(11) ?
C6A C7A C8A C9A . . . . 176.51(10) ?
N1A C7A C8A C10A . . . . 175.59(10) ?
C6A C7A C8A C10A . . . . -7.25(18) ?
N1A N2A C9A O1A . . . . -178.72(9) ?
N1A N2A C9A C8A . . . . 0.91(11) ?
C7A C8A C9A O1A . . . . 179.42(10) ?
C10A C8A C9A O1A . . . . 2.96(17) ?
C7A C8A C9A N2A . . . . -0.17(11) ?
C10A C8A C9A N2A . . . . -176.63(9) ?
C7B N1B N2B C9B . . . . -2.31(11) ?
C6B C1B C2B C3B . . . . -0.54(17) ?
C1B C2B C3B C4B . . . . 0.32(18) ?
C2B C3B C4B C5B . . . . 0.73(17) ?
C3B C4B C5B C6B . . . . -1.54(16) ?
C4B C5B C6B C1B . . . . 1.30(15) ?
C4B C5B C6B C7B . . . . -177.31(9) ?
C2B C1B C6B C5B . . . . -0.27(15) ?
C2B C1B C6B C7B . . . . 178.36(10) ?
N2B N1B C7B C8B . . . . 0.43(11) ?
N2B N1B C7B C6B . . . . 178.45(8) ?
C5B C6B C7B N1B . . . . 139.78(10) ?
C1B C6B C7B N1B . . . . -38.83(14) ?
C5B C6B C7B C8B . . . . -42.70(16) ?
C1B C6B C7B C8B . . . . 138.69(11) ?
N1B C7B C8B C9B . . . . 1.50(11) ?
C6B C7B C8B C9B . . . . -176.23(10) ?
N1B C7B C8B C10B . . . . -176.60(10) ?
C6B C7B C8B C10B . . . . 5.67(18) ?
N1B N2B C9B O1B . . . . -175.40(9) ?
N1B N2B C9B C8B . . . . 3.21(11) ?
C7B C8B C9B O1B . . . . 175.58(10) ?
C10B C8B C9B O1B . . . . -6.24(17) ?
C7B C8B C9B N2B . . . . -2.85(11) ?
C10B C8B C9B N2B . . . . 175.32(10) ?
