#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/90/2229071.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_2229071
loop_
_publ_author_name
'Shahani, Tara'
'Fun, Hoong-Kun'
'Ragavan, R. Venkat'
'Vijayakumar, V.'
'Venkatesh, M.'
_publ_section_title
;
 5-Ethyl-2-(4-fluorophenyl)-4-phenoxy-1H-pyrazol-3(2H)-one
;
_journal_coeditor_code           HB5788
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o475
_journal_paper_doi               10.1107/S1600536811000754
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C17 H15 F N2 O2'
_chemical_formula_moiety         'C17 H15 F N2 O2'
_chemical_formula_sum            'C17 H15 F N2 O2'
_chemical_formula_weight         298.31
_chemical_name_systematic
;
5-Ethyl-2-(4-fluorophenyl)-4-phenoxy-1H-pyrazol-3(2H)-one
;
_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                 109.916(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.332(2)
_cell_length_b                   8.6833(14)
_cell_length_c                   11.6066(19)
_cell_measurement_reflns_used    2971
_cell_measurement_temperature    100
_cell_measurement_theta_max      32.95
_cell_measurement_theta_min      3.00
_cell_volume                     1452.8(4)
_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
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII DUO CCD'
_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  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12927
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         3.00
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.239
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         4247
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0439
_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)+(0.0470P)²+0.4776P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1186
_reflns_number_gt                3207
_reflns_number_total             4247
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5788.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2229071
_cod_database_fobs_code          2229071
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
F F1 0.77686(5) 0.90535(11) 0.09196(7) 0.0332(2) Uani d . 1 . .
O O1 0.22938(6) 0.55499(11) 0.07275(8) 0.0226(2) Uani d . 1 . .
O O2 0.40598(6) 0.72722(11) 0.20071(7) 0.0243(2) Uani d . 1 . .
N N1 0.41488(7) 0.72695(13) 0.00442(8) 0.0187(2) Uani d . 1 . .
N N2 0.36358(7) 0.66422(13) -0.10812(9) 0.0192(2) Uani d . 1 . .
C C1 0.55898(8) 0.70430(15) -0.03872(10) 0.0191(2) Uani d . 1 . .
H H1A 0.5320 0.6289 -0.0969 0.023 Uiso calc R 1 . .
C C2 0.64946(9) 0.75124(16) -0.01831(11) 0.0215(3) Uani d . 1 . .
H H2A 0.6836 0.7098 -0.0634 0.026 Uiso calc R 1 . .
C C3 0.68736(8) 0.86072(16) 0.07039(11) 0.0222(3) Uani d . 1 . .
C C4 0.63952(9) 0.92659(15) 0.13937(11) 0.0215(3) Uani d . 1 . .
H H4A 0.6677 0.9992 0.1994 0.026 Uiso calc R 1 . .
C C5 0.54850(8) 0.88198(15) 0.11691(10) 0.0200(3) Uani d . 1 . .
H H5A 0.5142 0.9261 0.1607 0.024 Uiso calc R 1 . .
C C6 0.50869(8) 0.77049(14) 0.02820(10) 0.0172(2) Uani d . 1 . .
C C7 0.37115(8) 0.69697(15) 0.08861(10) 0.0187(2) Uani d . 1 . .
C C8 0.28708(8) 0.62287(15) 0.01905(10) 0.0190(2) Uani d . 1 . .
C C9 0.28418(8) 0.60586(15) -0.09962(10) 0.0190(2) Uani d . 1 . .
C C10 0.14644(8) 0.62813(16) 0.06414(11) 0.0204(3) Uani d . 1 . .
C C11 0.10224(9) 0.56911(18) 0.14043(11) 0.0254(3) Uani d . 1 . .
H H11A 0.1284 0.4881 0.1933 0.030 Uiso calc R 1 . .
C C12 0.01814(10) 0.6329(2) 0.13677(13) 0.0337(4) Uani d . 1 . .
H H12A -0.0120 0.5947 0.1880 0.040 Uiso calc R 1 . .
C C13 -0.02094(10) 0.7526(2) 0.05755(14) 0.0378(4) Uani d . 1 . .
H H13A -0.0772 0.7950 0.0554 0.045 Uiso calc R 1 . .
C C14 0.02428(10) 0.8092(2) -0.01883(13) 0.0330(3) Uani d . 1 . .
H H14A -0.0023 0.8892 -0.0727 0.040 Uiso calc R 1 . .
C C15 0.10888(9) 0.74771(17) -0.01581(11) 0.0252(3) Uani d . 1 . .
H H15A 0.1394 0.7863 -0.0665 0.030 Uiso calc R 1 . .
C C16 0.21135(9) 0.53400(17) -0.20637(11) 0.0246(3) Uani d . 1 . .
H H16A 0.1673 0.6127 -0.2491 0.030 Uiso calc R 1 . .
H H16B 0.1781 0.4578 -0.1764 0.030 Uiso calc R 1 . .
C C17 0.25005(10) 0.45693(18) -0.29685(12) 0.0282(3) Uani d . 1 . .
H H17A 0.2009 0.4051 -0.3590 0.042 Uiso calc R 1 . .
H H17B 0.2968 0.3836 -0.2542 0.042 Uiso calc R 1 . .
H H17C 0.2769 0.5336 -0.3342 0.042 Uiso calc R 1 . .
H H1N2 0.3689(12) 0.706(2) -0.1764(16) 0.035(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'
F F 0.0171 0.0103 '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
C8 O1 C10 . . 118.93(10) ?
C7 N1 N2 . . 109.59(10) ?
C7 N1 C6 . . 127.91(9) ?
N2 N1 C6 . . 119.98(9) ?
C9 N2 N1 . . 108.32(9) ?
C9 N2 H1N2 . . 124.6(11) ?
N1 N2 H1N2 . . 118.8(11) ?
C2 C1 C6 . . 119.70(11) ?
C2 C1 H1A . . 120.1 ?
C6 C1 H1A . . 120.1 ?
C3 C2 C1 . . 118.28(12) ?
C3 C2 H2A . . 120.9 ?
C1 C2 H2A . . 120.9 ?
F1 C3 C2 . . 118.39(12) ?
F1 C3 C4 . . 118.40(11) ?
C2 C3 C4 . . 123.20(12) ?
C3 C4 C5 . . 118.38(12) ?
C3 C4 H4A . . 120.8 ?
C5 C4 H4A . . 120.8 ?
C4 C5 C6 . . 119.55(11) ?
C4 C5 H5A . . 120.2 ?
C6 C5 H5A . . 120.2 ?
C1 C6 C5 . . 120.86(11) ?
C1 C6 N1 . . 119.90(11) ?
C5 C6 N1 . . 119.23(11) ?
O2 C7 N1 . . 123.71(11) ?
O2 C7 C8 . . 131.88(11) ?
N1 C7 C8 . . 104.34(10) ?
C9 C8 O1 . . 127.09(11) ?
C9 C8 C7 . . 109.42(11) ?
O1 C8 C7 . . 122.36(10) ?
N2 C9 C8 . . 108.11(10) ?
N2 C9 C16 . . 122.23(11) ?
C8 C9 C16 . . 129.65(12) ?
C15 C10 C11 . . 121.70(12) ?
C15 C10 O1 . . 123.51(11) ?
C11 C10 O1 . . 114.77(11) ?
C10 C11 C12 . . 118.95(13) ?
C10 C11 H11A . . 120.5 ?
C12 C11 H11A . . 120.5 ?
C13 C12 C11 . . 120.48(14) ?
C13 C12 H12A . . 119.8 ?
C11 C12 H12A . . 119.8 ?
C12 C13 C14 . . 119.58(14) ?
C12 C13 H13A . . 120.2 ?
C14 C13 H13A . . 120.2 ?
C13 C14 C15 . . 120.79(14) ?
C13 C14 H14A . . 119.6 ?
C15 C14 H14A . . 119.6 ?
C10 C15 C14 . . 118.50(13) ?
C10 C15 H15A . . 120.8 ?
C14 C15 H15A . . 120.8 ?
C9 C16 C17 . . 113.48(11) ?
C9 C16 H16A . . 108.9 ?
C17 C16 H16A . . 108.9 ?
C9 C16 H16B . . 108.9 ?
C17 C16 H16B . . 108.9 ?
H16A C16 H16B . . 107.7 ?
C16 C17 H17A . . 109.5 ?
C16 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C16 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 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
F1 C3 . 1.3644(14) ?
O1 C8 . 1.3763(15) ?
O1 C10 . 1.3941(15) ?
O2 C7 . 1.2544(14) ?
N1 C7 . 1.3851(15) ?
N1 N2 . 1.3862(13) ?
N1 C6 . 1.4202(16) ?
N2 C9 . 1.3529(16) ?
N2 H1N2 . 0.899(18) ?
C1 C2 . 1.3866(17) ?
C1 C6 . 1.3915(17) ?
C1 H1A . 0.9300 ?
C2 C3 . 1.3761(18) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.3806(18) ?
C4 C5 . 1.3848(17) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.3934(17) ?
C5 H5A . 0.9300 ?
C7 C8 . 1.4206(17) ?
C8 C9 . 1.3708(16) ?
C9 C16 . 1.4928(17) ?
C10 C15 . 1.3809(18) ?
C10 C11 . 1.3837(18) ?
C11 C12 . 1.3907(19) ?
C11 H11A . 0.9300 ?
C12 C13 . 1.382(2) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.388(2) ?
C13 H13A . 0.9300 ?
C14 C15 . 1.3922(19) ?
C14 H14A . 0.9300 ?
C15 H15A . 0.9300 ?
C16 C17 . 1.5255(19) ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 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
N2 H1N2 O2 4_575 0.899(18) 1.803(18) 2.6865(14) 167.1(16) yes
C11 H11A F1 2_645 0.93 2.52 3.3441(16) 147 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
C7 N1 N2 C9 . . . . 4.94(14) ?
C6 N1 N2 C9 . . . . 168.32(11) ?
C6 C1 C2 C3 . . . . 1.35(18) ?
C1 C2 C3 F1 . . . . 179.00(11) ?
C1 C2 C3 C4 . . . . -0.4(2) ?
F1 C3 C4 C5 . . . . 179.60(11) ?
C2 C3 C4 C5 . . . . -1.0(2) ?
C3 C4 C5 C6 . . . . 1.43(18) ?
C2 C1 C6 C5 . . . . -0.93(18) ?
C2 C1 C6 N1 . . . . 177.66(11) ?
C4 C5 C6 C1 . . . . -0.49(18) ?
C4 C5 C6 N1 . . . . -179.09(11) ?
C7 N1 C6 C1 . . . . 137.38(13) ?
N2 N1 C6 C1 . . . . -22.65(17) ?
C7 N1 C6 C5 . . . . -44.01(18) ?
N2 N1 C6 C5 . . . . 155.96(11) ?
N2 N1 C7 O2 . . . . 173.06(12) ?
C6 N1 C7 O2 . . . . 11.4(2) ?
N2 N1 C7 C8 . . . . -4.24(13) ?
C6 N1 C7 C8 . . . . -165.94(12) ?
C10 O1 C8 C9 . . . . -87.43(16) ?
C10 O1 C8 C7 . . . . 106.04(13) ?
O2 C7 C8 C9 . . . . -174.87(14) ?
N1 C7 C8 C9 . . . . 2.11(14) ?
O2 C7 C8 O1 . . . . -6.2(2) ?
N1 C7 C8 O1 . . . . 170.74(11) ?
N1 N2 C9 C8 . . . . -3.48(14) ?
N1 N2 C9 C16 . . . . 177.94(12) ?
O1 C8 C9 N2 . . . . -167.13(12) ?
C7 C8 C9 N2 . . . . 0.83(15) ?
O1 C8 C9 C16 . . . . 11.3(2) ?
C7 C8 C9 C16 . . . . 179.27(13) ?
C8 O1 C10 C15 . . . . 13.96(18) ?
C8 O1 C10 C11 . . . . -167.62(11) ?
C15 C10 C11 C12 . . . . -0.4(2) ?
O1 C10 C11 C12 . . . . -178.89(12) ?
C10 C11 C12 C13 . . . . 0.4(2) ?
C11 C12 C13 C14 . . . . 0.1(2) ?
C12 C13 C14 C15 . . . . -0.6(2) ?
C11 C10 C15 C14 . . . . -0.1(2) ?
O1 C10 C15 C14 . . . . 178.25(12) ?
C13 C14 C15 C10 . . . . 0.6(2) ?
N2 C9 C16 C17 . . . . 30.45(18) ?
C8 C9 C16 C17 . . . . -147.80(14) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656465
