#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/84/2228425.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2228425
loop_
_publ_author_name
'Shahani, Tara'
'Fun, Hoong-Kun'
'Ragavan, R. Venkat'
'Vijayakumar, V.'
'Venkatesh, M.'
_publ_section_title
;
 1-{[5-(4-Chlorophenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-yl]carbonyl]}piperidin-4-one
;
_journal_coeditor_code           IS2632
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3233
_journal_page_last               o3234
_journal_paper_doi               10.1107/S1600536810047215
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C21 H17 Cl F N3 O2'
_chemical_formula_moiety         'C21 H17 Cl F N3 O2'
_chemical_formula_sum            'C21 H17 Cl F N3 O2'
_chemical_formula_weight         397.83
_chemical_name_systematic
;
1-{[5-(4-Chlorophenyl)-1-(4-fluorophenyl)-1H-pyrazol-3-
yl]carbonyl]}piperidin-4-one
;
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                108.8370(10)
_cell_angle_beta                 104.7820(10)
_cell_angle_gamma                92.7920(10)
_cell_formula_units_Z            1
_cell_length_a                   6.0341(2)
_cell_length_b                   8.2500(3)
_cell_length_c                   10.2448(3)
_cell_measurement_reflns_used    9510
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      35.02
_cell_measurement_theta_min      2.19
_cell_volume                     461.90(3)
_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 0.986
_diffrn_measured_fraction_theta_max 0.986
_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  0.0195
_diffrn_reflns_av_sigmaI/netI    0.0210
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10178
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.19
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_T_max  0.9742
_exptl_absorpt_correction_T_min  0.8372
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             206
_exptl_crystal_size_max          0.77
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.215
_refine_ls_abs_structure_details 'Flack (1983), 1556 Friedel pairs'
_refine_ls_abs_structure_Flack   0.06(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3646
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0241
_refine_ls_R_factor_gt           0.0238
_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)+(0.0375P)²+0.0616P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0616
_refine_ls_wR_factor_ref         0.0620
_reflns_number_gt                3596
_reflns_number_total             3646
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            is2632.cif
_cod_data_source_block           I
_cod_database_code               2228425
_cod_database_fobs_code          2228425
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
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
Cl Cl1 -0.18751(5) -0.56629(4) -0.09987(4) 0.02699(9) Uani d . 1 . .
F F1 0.47475(18) -0.01865(15) -0.50052(9) 0.0397(3) Uani d . 1 . .
O O1 1.11635(17) 0.26727(13) 0.53957(10) 0.0225(2) Uani d . 1 . .
O O2 1.85032(19) 0.66828(16) 0.41014(12) 0.0326(3) Uani d . 1 . .
N N1 0.73866(19) 0.06297(14) 0.07455(11) 0.0160(2) Uani d . 1 . .
N N2 0.92725(19) 0.18040(14) 0.16028(11) 0.0171(2) Uani d . 1 . .
N N3 1.27132(19) 0.41856(15) 0.42751(11) 0.0197(2) Uani d . 1 . .
C C1 0.4556(2) 0.08181(18) -0.13442(14) 0.0192(3) Uani d . 1 . .
H H1A 0.3585 0.1228 -0.0774 0.023 Uiso calc R 1 . .
C C2 0.3886(3) 0.06260(19) -0.27928(14) 0.0235(3) Uani d . 1 . .
H H2A 0.2462 0.0894 -0.3215 0.028 Uiso calc R 1 . .
C C3 0.5399(3) 0.00258(19) -0.35841(14) 0.0254(3) Uani d . 1 . .
C C4 0.7542(3) -0.03780(19) -0.30190(14) 0.0243(3) Uani d . 1 . .
H H4A 0.8525 -0.0754 -0.3587 0.029 Uiso calc R 1 . .
C C5 0.8185(2) -0.02049(18) -0.15695(14) 0.0200(3) Uani d . 1 . .
H H5A 0.9602 -0.0487 -0.1154 0.024 Uiso calc R 1 . .
C C6 0.6687(2) 0.03934(16) -0.07542(13) 0.0161(2) Uani d . 1 . .
C C7 0.2588(2) -0.14175(17) 0.15655(13) 0.0173(3) Uani d . 1 . .
H H7A 0.2749 -0.0537 0.2437 0.021 Uiso calc R 1 . .
C C8 0.0689(2) -0.27130(18) 0.10073(14) 0.0190(3) Uani d . 1 . .
H H8A -0.0413 -0.2705 0.1498 0.023 Uiso calc R 1 . .
C C9 0.0469(2) -0.40181(17) -0.02954(15) 0.0192(3) Uani d . 1 . .
C C10 0.2091(3) -0.40594(18) -0.10451(15) 0.0199(3) Uani d . 1 . .
H H10A 0.1914 -0.4943 -0.1918 0.024 Uiso calc R 1 . .
C C11 0.3994(2) -0.27583(17) -0.04738(14) 0.0188(3) Uani d . 1 . .
H H11A 0.5098 -0.2778 -0.0966 0.023 Uiso calc R 1 . .
C C12 0.4254(2) -0.14175(16) 0.08395(13) 0.0160(3) Uani d . 1 . .
C C13 0.6292(2) -0.00678(16) 0.15007(13) 0.0151(2) Uani d . 1 . .
C C14 0.7564(2) 0.07058(17) 0.29276(13) 0.0172(3) Uani d . 1 . .
H H14A 0.7284 0.0510 0.3719 0.021 Uiso calc R 1 . .
C C15 0.9368(2) 0.18496(17) 0.29308(13) 0.0164(3) Uani d . 1 . .
C C16 1.1168(2) 0.29506(17) 0.42851(13) 0.0168(3) Uani d . 1 . .
C C17 1.2640(2) 0.49206(18) 0.31390(14) 0.0202(3) Uani d . 1 . .
H H17A 1.2384 0.6119 0.3472 0.024 Uiso calc R 1 . .
H H17B 1.1365 0.4287 0.2296 0.024 Uiso calc R 1 . .
C C18 1.4914(3) 0.48167(19) 0.27422(15) 0.0225(3) Uani d . 1 . .
H H18A 1.5073 0.3614 0.2298 0.027 Uiso calc R 1 . .
H H18B 1.4901 0.5391 0.2051 0.027 Uiso calc R 1 . .
C C19 1.6952(3) 0.56654(19) 0.40686(15) 0.0240(3) Uani d . 1 . .
C C20 1.6883(2) 0.5158(2) 0.53511(15) 0.0239(3) Uani d . 1 . .
H H20A 1.8015 0.5955 0.6202 0.029 Uiso calc R 1 . .
H H20B 1.7320 0.4010 0.5200 0.029 Uiso calc R 1 . .
C C21 1.4500(2) 0.51622(19) 0.56187(14) 0.0203(3) Uani d . 1 . .
H H21A 1.4476 0.4642 0.6341 0.024 Uiso calc R 1 . .
H H21B 1.4190 0.6344 0.5975 0.024 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
N2 N1 C13 . . 112.88(10) ?
N2 N1 C6 . . 118.05(11) ?
C13 N1 C6 . . 128.81(11) ?
C15 N2 N1 . . 104.32(11) ?
C16 N3 C21 . . 118.56(11) ?
C16 N3 C17 . . 128.10(11) ?
C21 N3 C17 . . 112.47(11) ?
C6 C1 C2 . . 119.43(13) ?
C6 C1 H1A . . 120.3 ?
C2 C1 H1A . . 120.3 ?
C3 C2 C1 . . 117.83(13) ?
C3 C2 H2A . . 121.1 ?
C1 C2 H2A . . 121.1 ?
F1 C3 C2 . . 118.27(13) ?
F1 C3 C4 . . 117.82(13) ?
C2 C3 C4 . . 123.90(12) ?
C3 C4 C5 . . 117.84(13) ?
C3 C4 H4A . . 121.1 ?
C5 C4 H4A . . 121.1 ?
C6 C5 C4 . . 119.19(12) ?
C6 C5 H5A . . 120.4 ?
C4 C5 H5A . . 120.4 ?
C5 C6 C1 . . 121.79(12) ?
C5 C6 N1 . . 119.07(11) ?
C1 C6 N1 . . 119.11(12) ?
C8 C7 C12 . . 121.09(12) ?
C8 C7 H7A . . 119.5 ?
C12 C7 H7A . . 119.5 ?
C9 C8 C7 . . 118.83(13) ?
C9 C8 H8A . . 120.6 ?
C7 C8 H8A . . 120.6 ?
C10 C9 C8 . . 121.64(13) ?
C10 C9 Cl1 . . 118.91(10) ?
C8 C9 Cl1 . . 119.45(11) ?
C9 C10 C11 . . 119.11(12) ?
C9 C10 H10A . . 120.4 ?
C11 C10 H10A . . 120.4 ?
C10 C11 C12 . . 120.45(13) ?
C10 C11 H11A . . 119.8 ?
C12 C11 H11A . . 119.8 ?
C7 C12 C11 . . 118.89(13) ?
C7 C12 C13 . . 119.32(11) ?
C11 C12 C13 . . 121.72(12) ?
N1 C13 C14 . . 105.49(12) ?
N1 C13 C12 . . 124.42(11) ?
C14 C13 C12 . . 130.04(12) ?
C13 C14 C15 . . 105.57(12) ?
C13 C14 H14A . . 127.2 ?
C15 C14 H14A . . 127.2 ?
N2 C15 C14 . . 111.75(11) ?
N2 C15 C16 . . 125.60(12) ?
C14 C15 C16 . . 122.64(11) ?
O1 C16 N3 . . 122.03(11) ?
O1 C16 C15 . . 116.83(12) ?
N3 C16 C15 . . 121.13(11) ?
N3 C17 C18 . . 110.09(11) ?
N3 C17 H17A . . 109.6 ?
C18 C17 H17A . . 109.6 ?
N3 C17 H17B . . 109.6 ?
C18 C17 H17B . . 109.6 ?
H17A C17 H17B . . 108.2 ?
C19 C18 C17 . . 110.61(11) ?
C19 C18 H18A . . 109.5 ?
C17 C18 H18A . . 109.5 ?
C19 C18 H18B . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 108.1 ?
O2 C19 C20 . . 122.68(13) ?
O2 C19 C18 . . 122.62(14) ?
C20 C19 C18 . . 114.69(13) ?
C19 C20 C21 . . 113.13(11) ?
C19 C20 H20A . . 109.0 ?
C21 C20 H20A . . 109.0 ?
C19 C20 H20B . . 109.0 ?
C21 C20 H20B . . 109.0 ?
H20A C20 H20B . . 107.8 ?
N3 C21 C20 . . 109.72(11) ?
N3 C21 H21A . . 109.7 ?
C20 C21 H21A . . 109.7 ?
N3 C21 H21B . . 109.7 ?
C20 C21 H21B . . 109.7 ?
H21A C21 H21B . . 108.2 ?
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
Cl1 C9 . 1.7387(14) ?
F1 C3 . 1.3570(14) ?
O1 C16 . 1.2317(16) ?
O2 C19 . 1.2130(19) ?
N1 N2 . 1.3558(15) ?
N1 C13 . 1.3701(17) ?
N1 C6 . 1.4299(15) ?
N2 C15 . 1.3352(16) ?
N3 C16 . 1.3515(18) ?
N3 C21 . 1.4657(15) ?
N3 C17 . 1.4684(17) ?
C1 C6 . 1.3875(19) ?
C1 C2 . 1.3881(18) ?
C1 H1A . 0.9300 ?
C2 C3 . 1.378(2) ?
C2 H2A . 0.9300 ?
C3 C4 . 1.379(2) ?
C4 C5 . 1.3927(18) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.3862(18) ?
C5 H5A . 0.9300 ?
C7 C8 . 1.3903(19) ?
C7 C12 . 1.3951(19) ?
C7 H7A . 0.9300 ?
C8 C9 . 1.3877(19) ?
C8 H8A . 0.9300 ?
C9 C10 . 1.385(2) ?
C10 C11 . 1.394(2) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.4045(18) ?
C11 H11A . 0.9300 ?
C12 C13 . 1.4714(18) ?
C13 C14 . 1.3823(17) ?
C14 C15 . 1.4039(19) ?
C14 H14A . 0.9300 ?
C15 C16 . 1.5004(17) ?
C17 C18 . 1.526(2) ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C18 C19 . 1.516(2) ?
C18 H18A . 0.9700 ?
C18 H18B . 0.9700 ?
C19 C20 . 1.511(2) ?
C20 C21 . 1.531(2) ?
C20 H20A . 0.9700 ?
C20 H20B . 0.9700 ?
C21 H21A . 0.9700 ?
C21 H21B . 0.9700 ?
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
C2 H2A O1 1_454 0.93 2.38 3.1196(19) 136 yes
C7 H7A F1 1_556 0.93 2.50 3.2099(15) 133 yes
C14 H14A F1 1_556 0.93 2.41 3.2614(17) 153 yes
C17 H17B N2 . 0.97 2.16 2.9091(18) 133 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
C13 N1 N2 C15 . . . . -0.07(13) ?
C6 N1 N2 C15 . . . . 174.57(11) ?
C6 C1 C2 C3 . . . . -0.5(2) ?
C1 C2 C3 F1 . . . . 179.21(13) ?
C1 C2 C3 C4 . . . . -0.6(2) ?
F1 C3 C4 C5 . . . . -178.30(12) ?
C2 C3 C4 C5 . . . . 1.5(2) ?
C3 C4 C5 C6 . . . . -1.3(2) ?
C4 C5 C6 C1 . . . . 0.3(2) ?
C4 C5 C6 N1 . . . . -177.75(12) ?
C2 C1 C6 C5 . . . . 0.6(2) ?
C2 C1 C6 N1 . . . . 178.67(12) ?
N2 N1 C6 C5 . . . . 62.36(15) ?
C13 N1 C6 C5 . . . . -123.97(15) ?
N2 N1 C6 C1 . . . . -115.72(14) ?
C13 N1 C6 C1 . . . . 57.94(19) ?
C12 C7 C8 C9 . . . . -0.09(18) ?
C7 C8 C9 C10 . . . . 0.12(19) ?
C7 C8 C9 Cl1 . . . . 179.22(10) ?
C8 C9 C10 C11 . . . . 0.13(19) ?
Cl1 C9 C10 C11 . . . . -178.98(10) ?
C9 C10 C11 C12 . . . . -0.41(19) ?
C8 C7 C12 C11 . . . . -0.19(18) ?
C8 C7 C12 C13 . . . . -177.17(11) ?
C10 C11 C12 C7 . . . . 0.44(19) ?
C10 C11 C12 C13 . . . . 177.34(12) ?
N2 N1 C13 C14 . . . . -0.21(14) ?
C6 N1 C13 C14 . . . . -174.15(12) ?
N2 N1 C13 C12 . . . . -177.66(11) ?
C6 N1 C13 C12 . . . . 8.4(2) ?
C7 C12 C13 N1 . . . . -146.36(12) ?
C11 C12 C13 N1 . . . . 36.75(19) ?
C7 C12 C13 C14 . . . . 36.9(2) ?
C11 C12 C13 C14 . . . . -140.04(14) ?
N1 C13 C14 C15 . . . . 0.40(14) ?
C12 C13 C14 C15 . . . . 177.65(12) ?
N1 N2 C15 C14 . . . . 0.34(14) ?
N1 N2 C15 C16 . . . . 179.57(11) ?
C13 C14 C15 N2 . . . . -0.47(15) ?
C13 C14 C15 C16 . . . . -179.73(11) ?
C21 N3 C16 O1 . . . . 2.92(18) ?
C17 N3 C16 O1 . . . . -165.56(13) ?
C21 N3 C16 C15 . . . . -177.10(11) ?
C17 N3 C16 C15 . . . . 14.4(2) ?
N2 C15 C16 O1 . . . . -171.13(13) ?
C14 C15 C16 O1 . . . . 8.02(18) ?
N2 C15 C16 N3 . . . . 8.88(19) ?
C14 C15 C16 N3 . . . . -171.97(12) ?
C16 N3 C17 C18 . . . . -127.53(14) ?
C21 N3 C17 C18 . . . . 63.42(14) ?
N3 C17 C18 C19 . . . . -54.44(15) ?
C17 C18 C19 O2 . . . . -132.83(14) ?
C17 C18 C19 C20 . . . . 46.56(16) ?
O2 C19 C20 C21 . . . . 134.59(15) ?
C18 C19 C20 C21 . . . . -44.80(16) ?
C16 N3 C21 C20 . . . . 129.76(13) ?
C17 N3 C21 C20 . . . . -60.04(15) ?
C19 C20 C21 N3 . . . . 49.66(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24666830
