#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/91/2229124.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_2229124
loop_
_publ_author_name
'Kargar, Hadi'
'Kia, Reza'
'Moghadamm, Majid'
'Tahir, Muhammad Nawaz'
_publ_section_title
;
 (Furan-2-yl)(5-hydroxy-3-methyl-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl)methanone
;
_journal_coeditor_code           JH2253
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o367
_journal_paper_doi               10.1107/S1600536811000948
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C15 H14 N2 O3'
_chemical_formula_moiety         'C15 H14 N2 O3'
_chemical_formula_sum            'C15 H14 N2 O3'
_chemical_formula_weight         270.28
_chemical_name_systematic
(Furan-2-yl)(5-hydroxy-3-methyl-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl)methanone
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 95.266(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.6844(10)
_cell_length_b                   8.4700(7)
_cell_length_c                   15.3022(16)
_cell_measurement_reflns_used    2245
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.45
_cell_measurement_theta_min      2.45
_cell_volume                     1379.0(2)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_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      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0444
_diffrn_reflns_av_sigmaI/netI    0.0418
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10534
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         25.24
_diffrn_reflns_theta_min         2.43
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9854
_exptl_absorpt_correction_T_min  0.9746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.127
_refine_ls_extinction_coef       0.0132(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2495
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0417
_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)+(0.0370P)²+0.1913P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.1058
_reflns_number_gt                1615
_reflns_number_total             2495
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jh2253.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2229124
_cod_database_fobs_code          2229124
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 O1 0.39871(12) 1.05521(16) 0.13086(9) 0.0564(4) Uani d . 1 . .
H H1 0.4501 1.0373 0.0954 0.085 Uiso calc R 1 . .
O O2 0.37249(12) 0.97468(15) -0.05954(9) 0.0540(4) Uani d . 1 . .
N N1 0.11933(14) 1.14352(17) 0.03952(12) 0.0530(5) Uani d . 1 . .
N N2 0.22305(14) 1.04995(17) 0.02389(10) 0.0463(4) Uani d . 1 . .
C C1 0.30125(18) 0.8002(2) 0.09202(12) 0.0467(5) Uani d . 1 . .
C C2 0.4147(2) 0.7260(2) 0.10936(14) 0.0605(6) Uani d . 1 . .
H H2 0.4856 0.7842 0.1289 0.073 Uiso calc R 1 . .
C C3 0.4242(3) 0.5637(3) 0.09779(18) 0.0803(8) Uani d . 1 . .
H H3 0.5016 0.5142 0.1091 0.096 Uiso calc R 1 . .
C C4 0.3208(3) 0.4768(3) 0.0700(2) 0.0916(9) Uani d . 1 . .
H H4 0.3272 0.3682 0.0630 0.110 Uiso calc R 1 . .
C C5 0.2085(3) 0.5500(3) 0.0528(2) 0.0909(9) Uani d . 1 . .
H H5 0.1378 0.4910 0.0337 0.109 Uiso calc R 1 . .
C C6 0.1979(2) 0.7105(2) 0.06307(16) 0.0704(7) Uani d . 1 . .
H H6 0.1203 0.7591 0.0504 0.085 Uiso calc R 1 . .
C C7 0.28639(17) 0.9765(2) 0.10487(13) 0.0455(5) Uani d . 1 . .
C C8 0.19276(18) 1.0218(2) 0.17109(14) 0.0569(6) Uani d . 1 . .
H H8A 0.1500 0.9292 0.1909 0.068 Uiso calc R 1 . .
H H8B 0.2350 1.0751 0.2216 0.068 Uiso calc R 1 . .
C C9 0.10301(18) 1.1294(2) 0.12079(15) 0.0545(5) Uani d . 1 . .
C C10 0.0004(2) 1.2167(3) 0.15998(16) 0.0818(8) Uani d . 1 . .
H H10A -0.0483 1.1441 0.1912 0.123 Uiso calc R 1 . .
H H10B -0.0530 1.2667 0.1142 0.123 Uiso calc R 1 . .
H H10C 0.0363 1.2955 0.1998 0.123 Uiso calc R 1 . .
C C11 0.27454(17) 1.0491(2) -0.05355(13) 0.0436(5) Uani d . 1 A .
C C12 0.21378(16) 1.1311(2) -0.12971(12) 0.0497(5) Uani d D 1 . .
C C13 0.1182(12) 1.2333(18) -0.1440(6) 0.071(3) Uani d PD 0.587(11) A 1
H H13A 0.0724 1.2811 -0.1024 0.085 Uiso calc PR 0.587(11) A 1
C C14 0.1026(12) 1.2525(13) -0.2367(6) 0.071(3) Uani d PD 0.587(11) A 1
H H14A 0.0360 1.3042 -0.2680 0.086 Uiso calc PR 0.587(11) A 1
C C15 0.1996(12) 1.1838(19) -0.2715(7) 0.076(3) Uani d PD 0.587(11) A 1
H H15A 0.2191 1.1926 -0.3293 0.092 Uiso calc PR 0.587(11) A 1
O O3 0.2646(7) 1.0983(13) -0.2065(3) 0.072(2) Uani d PD 0.587(11) A 1
C C13X 0.2557(15) 1.136(2) -0.2096(5) 0.060(4) Uani d PD 0.413(11) A 2
H H13B 0.3305 1.0955 -0.2267 0.072 Uiso calc PR 0.413(11) A 2
C C14X 0.1599(14) 1.2180(19) -0.2623(9) 0.058(3) Uani d PD 0.413(11) A 2
H H14B 0.1533 1.2220 -0.3233 0.070 Uiso calc PR 0.413(11) A 2
C C15X 0.0807(19) 1.2883(19) -0.2115(8) 0.079(4) Uani d PD 0.413(11) A 2
H H15B 0.0241 1.3695 -0.2263 0.095 Uiso calc PR 0.413(11) A 2
O O3X 0.1028(10) 1.212(2) -0.1327(7) 0.078(4) Uani d PD 0.413(11) A 2
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 . . 109.5 ?
C9 N1 N2 . . 107.11(16) ?
C11 N2 N1 . . 123.00(16) ?
C11 N2 C7 . . 122.41(15) ?
N1 N2 C7 . . 113.55(15) ?
C2 C1 C6 . . 118.50(19) ?
C2 C1 C7 . . 121.90(18) ?
C6 C1 C7 . . 119.60(17) ?
C1 C2 C3 . . 120.2(2) ?
C1 C2 H2 . . 119.9 ?
C3 C2 H2 . . 119.9 ?
C4 C3 C2 . . 120.5(2) ?
C4 C3 H3 . . 119.8 ?
C2 C3 H3 . . 119.8 ?
C5 C4 C3 . . 119.5(2) ?
C5 C4 H4 . . 120.3 ?
C3 C4 H4 . . 120.3 ?
C4 C5 C6 . . 120.7(2) ?
C4 C5 H5 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
C5 C6 C1 . . 120.7(2) ?
C5 C6 H6 . . 119.7 ?
C1 C6 H6 . . 119.7 ?
O1 C7 N2 . . 110.47(15) ?
O1 C7 C1 . . 114.13(15) ?
N2 C7 C1 . . 110.34(15) ?
O1 C7 C8 . . 106.70(15) ?
N2 C7 C8 . . 99.82(14) ?
C1 C7 C8 . . 114.43(16) ?
C9 C8 C7 . . 103.87(17) ?
C9 C8 H8A . . 111.0 ?
C7 C8 H8A . . 111.0 ?
C9 C8 H8B . . 111.0 ?
C7 C8 H8B . . 111.0 ?
H8A C8 H8B . . 109.0 ?
N1 C9 C8 . . 114.99(17) ?
N1 C9 C10 . . 121.0(2) ?
C8 C9 C10 . . 124.0(2) ?
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 . . 118.98(17) ?
O2 C11 C12 . . 120.23(17) ?
N2 C11 C12 . . 120.77(16) ?
C13X C12 C13 . . 98.3(7) ?
C13 C12 O3 . . 110.4(5) ?
C13X C12 O3X . . 108.3(7) ?
O3 C12 O3X . . 119.0(6) ?
C13X C12 C11 . . 125.7(6) ?
C13 C12 C11 . . 135.6(4) ?
O3 C12 C11 . . 114.0(4) ?
O3X C12 C11 . . 126.0(5) ?
C12 C13 C14 . . 104.7(6) ?
C12 C13 H13A . . 127.7 ?
C14 C13 H13A . . 127.7 ?
C15 C14 C13 . . 108.8(9) ?
C15 C14 H14A . . 125.6 ?
C13 C14 H14A . . 125.6 ?
C14 C15 O3 . . 107.5(8) ?
C14 C15 H15A . . 126.3 ?
O3 C15 H15A . . 126.3 ?
C12 O3 C15 . . 107.6(7) ?
C12 C13X C14X . . 104.4(8) ?
C12 C13X H13B . . 127.8 ?
C14X C13X H13B . . 127.8 ?
C15X C14X C13X . . 110.3(13) ?
C15X C14X H14B . . 124.8 ?
C13X C14X H14B . . 124.8 ?
C14X C15X O3X . . 103.6(11) ?
C14X C15X H15B . . 128.2 ?
O3X C15X H15B . . 128.2 ?
C12 O3X C15X . . 110.2(10) ?
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 . 1.398(2) ?
O1 H1 . 0.8200 ?
O2 C11 . 1.232(2) ?
N1 C9 . 1.277(2) ?
N1 N2 . 1.401(2) ?
N2 C11 . 1.352(2) ?
N2 C7 . 1.492(2) ?
C1 C2 . 1.370(3) ?
C1 C6 . 1.380(3) ?
C1 C7 . 1.516(3) ?
C2 C3 . 1.390(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.363(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.355(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.374(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C8 . 1.536(3) ?
C8 C9 . 1.486(3) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C10 . 1.493(3) ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 C12 . 1.457(2) ?
C12 C13X . 1.3407(11) ?
C12 C13 . 1.3407(10) ?
C12 O3 . 1.3670(10) ?
C12 O3X . 1.3677(10) ?
C13 C14 . 1.4230(11) ?
C13 H13A . 0.9300 ?
C14 C15 . 1.3407(10) ?
C14 H14A . 0.9300 ?
C15 O3 . 1.3679(10) ?
C15 H15A . 0.9300 ?
C13X C14X . 1.4230(10) ?
C13X H13B . 0.9300 ?
C14X C15X . 1.3406(10) ?
C14X H14B . 0.9300 ?
C15X O3X . 1.3679(10) ?
C15X H15B . 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 O2 3_675 0.82 2.02 2.7786(18) 153 y
C14 H14A O1 4_585 0.93 2.36 3.271(9) 168 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 . . . . -173.27(17) ?
C9 N1 N2 C7 . . . . -4.7(2) ?
C6 C1 C2 C3 . . . . 0.0(3) ?
C7 C1 C2 C3 . . . . 179.19(19) ?
C1 C2 C3 C4 . . . . -0.7(4) ?
C2 C3 C4 C5 . . . . 0.7(4) ?
C3 C4 C5 C6 . . . . -0.1(4) ?
C4 C5 C6 C1 . . . . -0.6(4) ?
C2 C1 C6 C5 . . . . 0.6(3) ?
C7 C1 C6 C5 . . . . -178.6(2) ?
C11 N2 C7 O1 . . . . 64.3(2) ?
N1 N2 C7 O1 . . . . -104.43(16) ?
C11 N2 C7 C1 . . . . -62.9(2) ?
N1 N2 C7 C1 . . . . 128.44(15) ?
C11 N2 C7 C8 . . . . 176.34(16) ?
N1 N2 C7 C8 . . . . 7.66(18) ?
C2 C1 C7 O1 . . . . 3.3(3) ?
C6 C1 C7 O1 . . . . -177.48(18) ?
C2 C1 C7 N2 . . . . 128.39(19) ?
C6 C1 C7 N2 . . . . -52.4(2) ?
C2 C1 C7 C8 . . . . -120.0(2) ?
C6 C1 C7 C8 . . . . 59.2(2) ?
O1 C7 C8 C9 . . . . 107.68(17) ?
N2 C7 C8 C9 . . . . -7.31(18) ?
C1 C7 C8 C9 . . . . -125.09(17) ?
N2 N1 C9 C8 . . . . -0.9(2) ?
N2 N1 C9 C10 . . . . 179.00(18) ?
C7 C8 C9 N1 . . . . 5.7(2) ?
C7 C8 C9 C10 . . . . -174.22(19) ?
N1 N2 C11 O2 . . . . 173.43(16) ?
C7 N2 C11 O2 . . . . 5.8(2) ?
N1 N2 C11 C12 . . . . -8.3(3) ?
C7 N2 C11 C12 . . . . -175.89(16) ?
O2 C11 C12 C13X . . . . -0.8(13) ?
N2 C11 C12 C13X . . . . -179.1(12) ?
O2 C11 C12 C13 . . . . -171.2(12) ?
N2 C11 C12 C13 . . . . 10.5(13) ?
O2 C11 C12 O3 . . . . 8.7(6) ?
N2 C11 C12 O3 . . . . -169.6(5) ?
O2 C11 C12 O3X . . . . 177.3(10) ?
N2 C11 C12 O3X . . . . -1.0(11) ?
C13X C12 C13 C14 . . . . 13.4(15) ?
O3 C12 C13 C14 . . . . 5.6(16) ?
O3X C12 C13 C14 . . . . -128(6) ?
C11 C12 C13 C14 . . . . -174.5(6) ?
C12 C13 C14 C15 . . . . -9.9(18) ?
C13 C14 C15 O3 . . . . 10.3(19) ?
C13X C12 O3 C15 . . . . -33(5) ?
C13 C12 O3 C15 . . . . 0.5(15) ?
O3X C12 O3 C15 . . . . 11.1(13) ?
C11 C12 O3 C15 . . . . -179.5(9) ?
C14 C15 O3 C12 . . . . -6.8(17) ?
C13 C12 C13X C14X . . . . -11.5(17) ?
O3 C12 C13X C14X . . . . 137(6) ?
O3X C12 C13X C14X . . . . -3(2) ?
C11 C12 C13X C14X . . . . 175.3(9) ?
C12 C13X C14X C15X . . . . 14(2) ?
C13X C14X C15X O3X . . . . -18(2) ?
C13X C12 O3X C15X . . . . -8(2) ?
C13 C12 O3X C15X . . . . 32(5) ?
O3 C12 O3X C15X . . . . -18.4(19) ?
C11 C12 O3X C15X . . . . 173.5(11) ?
C14X C15X O3X C12 . . . . 16(2) ?
