#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/88/2228815.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_2228815
loop_
_publ_author_name
'Kargar, Hadi'
'Kia, Reza'
'Froozandeh, Fatemeh'
'Hossaini Sadr, Moayad'
'Tahir, Muhammad Nawaz'
_publ_section_title
;
 (5-Hydroxy-3-methyl-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl)(pyridin-4-yl)methanone
 monohydrate
;
_journal_coeditor_code           LH5187
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o209
_journal_paper_doi               10.1107/S160053681005275X
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C16 H15 N3 O2, H2 O'
_chemical_formula_moiety         'C16 H15 N3 O2, H2 O'
_chemical_formula_sum            'C16 H17 N3 O3'
_chemical_formula_weight         299.33
_chemical_name_systematic
'(5-Hydroxy-3-methyl-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl)(pyridin-4-yl)methanone monohydrate'
_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                 93.004(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.9676(10)
_cell_length_b                   7.0266(5)
_cell_length_c                   12.6135(6)
_cell_measurement_reflns_used    2540
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.45
_cell_volume                     1501.77(16)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)'
_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      296(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_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  0.0382
_diffrn_reflns_av_sigmaI/netI    0.0546
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8525
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         2.40
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9834
_exptl_absorpt_correction_T_min  0.9708
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.179
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3059
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0875
_refine_ls_R_factor_gt           0.0481
_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)+(0.0554P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1205
_reflns_number_gt                1916
_reflns_number_total             3059
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5187.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2228815
_cod_database_fobs_code          2228815
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
O O1 0.32045(8) 0.3424(2) -0.01490(10) 0.0461(4) Uani d . 1 . .
H H1 0.2849 0.2478 -0.0322 0.069 Uiso d R 1 . .
O O2 0.22503(8) 0.70361(19) 0.00147(10) 0.0455(4) Uani d . 1 . .
O O1W 0.21323(8) 0.4293(2) 0.41563(10) 0.0522(4) Uani d . 1 . .
H H1W1 0.2123 0.5449 0.4498 0.078 Uiso d R 1 . .
H H2W1 0.1656 0.3911 0.4143 0.078 Uiso d R 1 . .
N N1 0.17899(8) 0.3038(2) 0.15669(11) 0.0339(4) Uani d . 1 . .
N N2 0.22186(8) 0.4400(2) 0.10150(11) 0.0347(4) Uani d . 1 . .
N N3 -0.05005(9) 0.7733(2) 0.10396(13) 0.0431(4) Uani d . 1 . .
C C1 0.36077(10) 0.5444(3) 0.12956(14) 0.0370(5) Uani d . 1 . .
C C2 0.35148(13) 0.6223(3) 0.22873(16) 0.0544(6) Uani d . 1 . .
H H2 0.3115 0.5788 0.2703 0.065 Uiso calc R 1 . .
C C3 0.40176(17) 0.7653(4) 0.2661(2) 0.0726(8) Uani d . 1 . .
H H3A 0.3947 0.8188 0.3323 0.087 Uiso calc R 1 . .
C C4 0.46131(16) 0.8286(4) 0.2071(3) 0.0770(8) Uani d . 1 . .
H H4 0.4951 0.9238 0.2333 0.092 Uiso calc R 1 . .
C C5 0.47118(14) 0.7520(4) 0.1099(2) 0.0726(8) Uani d . 1 . .
H H5 0.5119 0.7947 0.0694 0.087 Uiso calc R 1 . .
C C6 0.42080(12) 0.6104(3) 0.07061(17) 0.0521(6) Uani d . 1 . .
H H6 0.4277 0.5596 0.0036 0.062 Uiso calc R 1 . .
C C7 0.30659(10) 0.3854(3) 0.09099(13) 0.0359(5) Uani d . 1 . .
C C8 0.31075(11) 0.2087(3) 0.16286(16) 0.0449(5) Uani d . 1 . .
H H8A 0.3310 0.1000 0.1255 0.054 Uiso calc R 1 . .
H H8B 0.3443 0.2320 0.2262 0.054 Uiso calc R 1 . .
C C9 0.22789(11) 0.1762(3) 0.19037(13) 0.0339(4) Uani d . 1 . .
C C10 0.20331(12) 0.0106(3) 0.25333(15) 0.0469(5) Uani d . 1 . .
H H10A 0.1476 0.0176 0.2628 0.070 Uiso calc R 1 . .
H H10B 0.2314 0.0116 0.3214 0.070 Uiso calc R 1 . .
H H10C 0.2150 -0.1048 0.2166 0.070 Uiso calc R 1 . .
C C11 0.18790(11) 0.5957(3) 0.05705(13) 0.0334(4) Uani d . 1 . .
C C12 0.10340(10) 0.6415(2) 0.07655(13) 0.0297(4) Uani d . 1 . .
C C13 0.07060(11) 0.6357(3) 0.17484(14) 0.0375(5) Uani d . 1 . .
H H13 0.0990 0.5858 0.2335 0.045 Uiso calc R 1 . .
C C14 -0.00432(12) 0.7045(3) 0.18447(15) 0.0430(5) Uani d . 1 . .
H H14 -0.0247 0.7031 0.2515 0.052 Uiso calc R 1 . .
C C15 -0.01844(11) 0.7738(3) 0.00927(15) 0.0407(5) Uani d . 1 . .
H H15 -0.0493 0.8176 -0.0488 0.049 Uiso calc R 1 . .
C C16 0.05681(11) 0.7135(3) -0.00760(14) 0.0361(5) Uani d . 1 . .
H H16 0.0764 0.7210 -0.0750 0.043 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
C7 O1 H1 . . 104.0 ?
H1W1 O1W H2W1 . . 104.4 ?
C9 N1 N2 . . 107.33(14) ?
C11 N2 N1 . . 122.54(15) ?
C11 N2 C7 . . 124.25(15) ?
N1 N2 C7 . . 113.06(13) ?
C15 N3 C14 . . 115.90(17) ?
C6 C1 C2 . . 118.6(2) ?
C6 C1 C7 . . 122.12(17) ?
C2 C1 C7 . . 119.22(17) ?
C1 C2 C3 . . 119.9(2) ?
C1 C2 H2 . . 120.1 ?
C3 C2 H2 . . 120.1 ?
C4 C3 C2 . . 120.9(2) ?
C4 C3 H3A . . 119.5 ?
C2 C3 H3A . . 119.5 ?
C5 C4 C3 . . 119.6(2) ?
C5 C4 H4 . . 120.2 ?
C3 C4 H4 . . 120.2 ?
C4 C5 C6 . . 120.3(2) ?
C4 C5 H5 . . 119.9 ?
C6 C5 H5 . . 119.9 ?
C1 C6 C5 . . 120.7(2) ?
C1 C6 H6 . . 119.7 ?
C5 C6 H6 . . 119.7 ?
O1 C7 N2 . . 110.42(13) ?
O1 C7 C1 . . 109.67(14) ?
N2 C7 C1 . . 110.60(15) ?
O1 C7 C8 . . 112.56(16) ?
N2 C7 C8 . . 99.74(14) ?
C1 C7 C8 . . 113.51(15) ?
C9 C8 C7 . . 104.34(15) ?
C9 C8 H8A . . 110.9 ?
C7 C8 H8A . . 110.9 ?
C9 C8 H8B . . 110.9 ?
C7 C8 H8B . . 110.9 ?
H8A C8 H8B . . 108.9 ?
N1 C9 C10 . . 122.21(17) ?
N1 C9 C8 . . 114.87(16) ?
C10 C9 C8 . . 122.91(17) ?
C9 C10 H10A . . 109.5 ?
C9 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C9 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
O2 C11 N2 . . 121.24(17) ?
O2 C11 C12 . . 118.90(16) ?
N2 C11 C12 . . 119.85(16) ?
C16 C12 C13 . . 117.15(17) ?
C16 C12 C11 . . 117.65(15) ?
C13 C12 C11 . . 124.86(16) ?
C14 C13 C12 . . 119.10(17) ?
C14 C13 H13 . . 120.4 ?
C12 C13 H13 . . 120.4 ?
N3 C14 C13 . . 124.36(18) ?
N3 C14 H14 . . 117.8 ?
C13 C14 H14 . . 117.8 ?
N3 C15 C16 . . 123.97(17) ?
N3 C15 H15 . . 118.0 ?
C16 C15 H15 . . 118.0 ?
C15 C16 C12 . . 119.47(17) ?
C15 C16 H16 . . 120.3 ?
C12 C16 H16 . . 120.3 ?
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 C7 . 1.401(2) ?
O1 H1 . 0.9166 ?
O2 C11 . 1.229(2) ?
O1W H1W1 . 0.9200 ?
O1W H2W1 . 0.8517 ?
N1 C9 . 1.279(2) ?
N1 N2 . 1.408(2) ?
N2 C11 . 1.345(2) ?
N2 C7 . 1.501(2) ?
N3 C15 . 1.334(2) ?
N3 C14 . 1.336(2) ?
C1 C6 . 1.373(3) ?
C1 C2 . 1.382(3) ?
C1 C7 . 1.511(3) ?
C2 C3 . 1.384(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.360(4) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.358(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.386(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C8 . 1.536(3) ?
C8 C9 . 1.483(3) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.481(3) ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 C12 . 1.502(2) ?
C12 C16 . 1.386(2) ?
C12 C13 . 1.386(2) ?
C13 C14 . 1.371(3) ?
C13 H13 . 0.9300 ?
C14 H14 . 0.9300 ?
C15 C16 . 1.372(3) ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
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 O1W 4_565 0.92 1.84 2.7490(19) 172.6 y
O1W H1W1 O2 4_576 0.92 1.89 2.8003(19) 169.0 y
O1W H2W1 N3 2_545 0.85 2.13 2.976(2) 173.2 y
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
C9 N1 N2 C11 . . . . -179.02(16) ?
C9 N1 N2 C7 . . . . 5.31(18) ?
C6 C1 C2 C3 . . . . 0.6(3) ?
C7 C1 C2 C3 . . . . 178.63(19) ?
C1 C2 C3 C4 . . . . -1.1(4) ?
C2 C3 C4 C5 . . . . 0.7(4) ?
C3 C4 C5 C6 . . . . 0.2(4) ?
C2 C1 C6 C5 . . . . 0.2(3) ?
C7 C1 C6 C5 . . . . -177.7(2) ?
C4 C5 C6 C1 . . . . -0.6(4) ?
C11 N2 C7 O1 . . . . -64.9(2) ?
N1 N2 C7 O1 . . . . 110.71(15) ?
C11 N2 C7 C1 . . . . 56.7(2) ?
N1 N2 C7 C1 . . . . -127.72(15) ?
C11 N2 C7 C8 . . . . 176.49(17) ?
N1 N2 C7 C8 . . . . -7.92(18) ?
C6 C1 C7 O1 . . . . -8.6(2) ?
C2 C1 C7 O1 . . . . 173.52(17) ?
C6 C1 C7 N2 . . . . -130.57(19) ?
C2 C1 C7 N2 . . . . 51.5(2) ?
C6 C1 C7 C8 . . . . 118.3(2) ?
C2 C1 C7 C8 . . . . -59.6(2) ?
O1 C7 C8 C9 . . . . -109.82(17) ?
N2 C7 C8 C9 . . . . 7.23(18) ?
C1 C7 C8 C9 . . . . 124.87(16) ?
N2 N1 C9 C10 . . . . 179.31(16) ?
N2 N1 C9 C8 . . . . 0.2(2) ?
C7 C8 C9 N1 . . . . -5.2(2) ?
C7 C8 C9 C10 . . . . 175.69(17) ?
N1 N2 C11 O2 . . . . -173.53(15) ?
C7 N2 C11 O2 . . . . 1.7(3) ?
N1 N2 C11 C12 . . . . 7.4(2) ?
C7 N2 C11 C12 . . . . -177.38(15) ?
O2 C11 C12 C16 . . . . 39.6(2) ?
N2 C11 C12 C16 . . . . -141.39(18) ?
O2 C11 C12 C13 . . . . -133.48(19) ?
N2 C11 C12 C13 . . . . 45.6(3) ?
C16 C12 C13 C14 . . . . -1.5(3) ?
C11 C12 C13 C14 . . . . 171.52(18) ?
C15 N3 C14 C13 . . . . -0.4(3) ?
C12 C13 C14 N3 . . . . 2.0(3) ?
C14 N3 C15 C16 . . . . -1.7(3) ?
N3 C15 C16 C12 . . . . 2.1(3) ?
C13 C12 C16 C15 . . . . -0.4(3) ?
C11 C12 C16 C15 . . . . -173.97(17) ?
