#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/29/2212924.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_2212924
loop_
_publ_author_name
'Wan, Wen'
'Ma, Guo-Bin'
'Yuan, Zong-Qian'
'Li, Ming-Xing'
'Hao, Jian'
_publ_section_title
;
 5,5,5-Trifluoro-N-(4-fluorophenyl)-4-hydroxypentanamide
;
_journal_coeditor_code           HK2195
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1685
_journal_page_last               o1686
_journal_paper_doi               10.1107/S1600536807010422
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C11 H11 F4 N O2'
_chemical_formula_moiety         'C11 H11 F4 N O2'
_chemical_formula_sum            'C11 H11 F4 N O2'
_chemical_formula_weight         265.21
_chemical_name_systematic
;
5,5,5-Trifluoro-N-(4-fluorophenyl)-4-hydroxypentanamide
;
_space_group_IT_number           56
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.162(2)
_cell_length_b                   23.153(4)
_cell_length_c                   8.5893(14)
_cell_measurement_reflns_used    3340
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      22.81
_cell_measurement_theta_min      3.03
_cell_volume                     2418.6(7)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2000)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART 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  0.0424
_diffrn_reflns_av_sigmaI/netI    0.0300
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11531
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         3.03
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_T_max  0.9725
_exptl_absorpt_correction_T_min  0.9591
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.183
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2142
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0464
_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)+(0.0713P)²+0.6158P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1381
_reflns_number_gt                1557
_reflns_number_total             2142
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2195.cif
_cod_data_source_block           3
_cod_database_code               2212924
_cod_database_fobs_code          2212924
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, 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
F F1 0.63780(17) 0.70671(9) 0.1727(3) 0.1277(8) Uani d . 1
F F2 0.61515(15) 0.30221(6) 1.15861(19) 0.0931(6) Uani d . 1
F F3 0.75984(14) 0.33225(6) 1.0436(2) 0.0853(5) Uani d . 1
F F4 0.63064(16) 0.29254(6) 0.9123(2) 0.0948(6) Uani d . 1
C C1 0.6219(2) 0.66753(12) 0.2882(4) 0.0785(8) Uani d . 1
C C2 0.6686(2) 0.61488(13) 0.2745(3) 0.0788(8) Uani d . 1
H H2 0.7123 0.6061 0.1889 0.095 Uiso calc R 1
C C3 0.6503(2) 0.57403(11) 0.3904(3) 0.0661(7) Uani d . 1
H H3 0.6815 0.5375 0.3823 0.079 Uiso calc R 1
C C4 0.58628(16) 0.58767(9) 0.5167(2) 0.0477(5) Uani d . 1
C C5 0.5374(3) 0.64079(11) 0.5245(3) 0.0782(8) Uani d . 1
H H5 0.4915 0.6496 0.6077 0.094 Uiso calc R 1
C C6 0.5557(3) 0.68140(13) 0.4096(4) 0.0992(11) Uani d . 1
H H6 0.5231 0.7177 0.4153 0.119 Uiso calc R 1
C C7 0.62436(16) 0.50256(9) 0.6833(2) 0.0459(5) Uani d . 1
C C8 0.58733(17) 0.47352(10) 0.8314(2) 0.0527(6) Uani d . 1
H H8A 0.5081 0.4689 0.8282 0.063 Uiso calc R 1
H H8B 0.6046 0.4985 0.9188 0.063 Uiso calc R 1
C C9 0.63946(18) 0.41523(9) 0.8586(2) 0.0510(5) Uani d . 1
H H9A 0.7185 0.4199 0.8661 0.061 Uiso calc R 1
H H9B 0.6243 0.3905 0.7701 0.061 Uiso calc R 1
C C10 0.59759(16) 0.38628(9) 1.0057(2) 0.0478(5) Uani d . 1
H H10 0.5185 0.3798 0.9929 0.057 Uiso calc R 1
C C11 0.6512(2) 0.32834(10) 1.0299(3) 0.0631(6) Uani d . 1
N N1 0.56458(14) 0.54842(7) 0.64051(19) 0.0492(5) Uani d . 1
H H1 0.5062 0.5550 0.6941 0.059 Uiso calc R 1
O O1 0.70526(13) 0.48602(7) 0.61034(18) 0.0625(5) Uani d . 1
O O2 0.61248(11) 0.42015(6) 1.14061(15) 0.0481(4) Uani d . 1
H H2A 0.6726 0.4361 1.1369 0.072 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 122.0(2) ?
C2 C1 F1 118.7(3) ?
C6 C1 F1 119.2(3) ?
C1 C2 C3 119.0(2) ?
C1 C2 H2 120.5 ?
C3 C2 H2 120.5 ?
C4 C3 C2 120.0(2) ?
C4 C3 H3 120.0 ?
C2 C3 H3 120.0 ?
C5 C4 C3 119.5(2) ?
C5 C4 N1 117.16(19) ?
C3 C4 N1 123.29(19) y
C4 C5 C6 120.5(3) ?
C4 C5 H5 119.8 ?
C6 C5 H5 119.8 ?
C1 C6 C5 118.9(3) ?
C1 C6 H6 120.5 ?
C5 C6 H6 120.5 ?
O1 C7 N1 122.84(19) ?
O1 C7 C8 122.08(18) ?
N1 C7 C8 115.05(18) ?
C7 C8 C9 113.83(18) ?
C7 C8 H8A 108.8 ?
C9 C8 H8A 108.8 ?
C7 C8 H8B 108.8 ?
C9 C8 H8B 108.8 ?
H8A C8 H8B 107.7 ?
C8 C9 C10 112.50(17) ?
C8 C9 H9A 109.1 ?
C10 C9 H9A 109.1 ?
C8 C9 H9B 109.1 ?
C10 C9 H9B 109.1 ?
H9A C9 H9B 107.8 ?
O2 C10 C11 109.04(17) y
O2 C10 C9 113.27(16) y
C11 C10 C9 111.29(18) ?
O2 C10 H10 107.7 ?
C11 C10 H10 107.7 ?
C9 C10 H10 107.7 ?
F3 C11 F4 107.2(2) ?
F3 C11 F2 106.5(2) y
F4 C11 F2 106.57(19) ?
F3 C11 C10 112.43(19) ?
F4 C11 C10 111.7(2) ?
F2 C11 C10 112.1(2) y
C7 N1 C4 127.66(17) y
C7 N1 H1 116.2 ?
C4 N1 H1 116.2 ?
C10 O2 H2A 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
F1 C1 1.358(3) ?
F2 C11 1.334(3) y
F3 C11 1.330(3) ?
F4 C11 1.330(3) ?
C1 C2 1.350(4) ?
C1 C6 1.356(4) ?
C2 C3 1.391(3) ?
C2 H2 0.9300 ?
C3 C4 1.372(3) ?
C3 H3 0.9300 ?
C4 C5 1.368(3) ?
C4 N1 1.424(3) ?
C5 C6 1.381(4) ?
C5 H5 0.9300 ?
C6 H6 0.9300 ?
C7 O1 1.228(2) y
C7 N1 1.339(3) y
C7 C8 1.507(3) ?
C8 C9 1.509(3) ?
C8 H8A 0.9700 ?
C8 H8B 0.9700 ?
C9 C10 1.518(3) y
C9 H9A 0.9700 ?
C9 H9B 0.9700 ?
C10 O2 1.411(2) y
C10 C11 1.506(3) y
C10 H10 0.9800 ?
N1 H1 0.8600 ?
O2 H2A 0.8200 ?
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
N1 H1 O2 5_667 0.86 2.10 2.950(2) 167.3
O2 H2A O1 8_756 0.82 1.90 2.703(2) 168.0
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21124994
