#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/63/2226335.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_2226335
loop_
_publ_author_name
'Tang, Long'
'Wu, Ya-Pan'
'Fu, Feng'
'Zhang, Zhu-Lian'
'Zheng, Dan'
_publ_section_title
;
 4,4'-(1,1,1,3,3,3-Hexafluoropropane-2,2-diyl)dibenzoic acid
;
_journal_coeditor_code           XU2737
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1390
_journal_paper_doi               10.1107/S1600536810017745
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C17 H10 F6 O4'
_chemical_formula_moiety         'C17 H10 F6 O4'
_chemical_formula_sum            'C17 H10 F6 O4'
_chemical_formula_weight         392.25
_chemical_name_systematic
;
4,4'-(1,1,1,3,3,3-Hexafluoropropane-2,2-diyl)dibenzoic acid
;
_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                 102.294(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.7523(16)
_cell_length_b                   13.381(3)
_cell_length_c                   16.134(3)
_cell_measurement_reflns_used    775
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.71
_cell_measurement_theta_min      2.69
_cell_volume                     1635.3(6)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0533
_diffrn_reflns_av_sigmaI/netI    0.0832
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8113
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         2.00
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.189
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         2904
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.1048
_refine_ls_R_factor_gt           0.0403
_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)+(0.0135P)²+0.1900P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0639
_refine_ls_wR_factor_ref         0.0708
_reflns_number_gt                1339
_reflns_number_total             2904
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            xu2737.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed
to 'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        1635.2(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2226335
_cod_database_fobs_code          2226335
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
C C1 -0.2346(4) 0.0955(2) 0.4514(2) 0.0540(8) Uani d . 1 . .
C C2 -0.1474(3) 0.04538(17) 0.38975(18) 0.0467(7) Uani d . 1 . .
C C3 0.0256(3) 0.06770(16) 0.38831(17) 0.0482(7) Uani d . 1 . .
H H3 0.0908 0.1094 0.4295 0.058 Uiso calc R 1 . .
C C4 0.1019(3) 0.02807(17) 0.32574(17) 0.0491(7) Uani d . 1 . .
H H4 0.2188 0.0435 0.3254 0.059 Uiso calc R 1 . .
C C5 0.0090(3) -0.03396(17) 0.26363(17) 0.0438(7) Uani d . 1 . .
C C6 -0.1618(3) -0.05959(18) 0.26780(19) 0.0599(8) Uani d . 1 . .
H H6 -0.2251 -0.1042 0.2286 0.072 Uiso calc R 1 . .
C C7 -0.2381(3) -0.01936(19) 0.32963(19) 0.0612(8) Uani d . 1 . .
H H7 -0.3539 -0.0363 0.3309 0.073 Uiso calc R 1 . .
C C8 0.1010(3) -0.07485(17) 0.19469(18) 0.0430(7) Uani d . 1 . .
C C9 0.2103(4) -0.1652(2) 0.2347(2) 0.0584(8) Uani d . 1 . .
C C10 -0.0290(4) -0.1105(2) 0.1152(2) 0.0586(8) Uani d . 1 . .
C C11 0.2132(3) 0.00552(17) 0.16376(15) 0.0412(7) Uani d . 1 . .
C C12 0.1452(3) 0.10175(17) 0.14883(16) 0.0489(7) Uani d . 1 . .
H H12 0.0372 0.1171 0.1621 0.059 Uiso calc R 1 . .
C C13 0.2346(3) 0.17475(18) 0.11477(16) 0.0500(7) Uani d . 1 . .
H H13 0.1856 0.2382 0.1045 0.060 Uiso calc R 1 . .
C C14 0.3958(3) 0.15424(18) 0.09593(16) 0.0460(7) Uani d . 1 . .
C C15 0.4658(3) 0.05969(19) 0.11157(18) 0.0609(8) Uani d . 1 . .
H H15 0.5758 0.0454 0.1002 0.073 Uiso calc R 1 . .
C C16 0.3744(3) -0.01372(19) 0.14386(17) 0.0575(8) Uani d . 1 . .
H H16 0.4223 -0.0776 0.1524 0.069 Uiso calc R 1 . .
C C17 0.4938(4) 0.2307(2) 0.05836(17) 0.0513(8) Uani d . 1 . .
O O1 -0.1535(2) 0.15916(13) 0.50126(12) 0.0654(6) Uani d . 1 . .
O O2 -0.3969(3) 0.07246(13) 0.44691(15) 0.0814(7) Uani d . 1 . .
H H2A -0.4415 0.1127 0.4745 0.098 Uiso calc R 1 . .
O O3 0.6508(3) 0.20695(12) 0.05373(14) 0.0748(6) Uani d . 1 . .
H H3A 0.7020 0.2563 0.0408 0.090 Uiso calc R 1 . .
O O4 0.4229(2) 0.31255(13) 0.03316(12) 0.0628(6) Uani d . 1 . .
F F1 -0.14945(18) -0.04108(11) 0.08519(10) 0.0701(5) Uani d . 1 . .
F F2 -0.11835(19) -0.19326(11) 0.12709(10) 0.0760(5) Uani d . 1 . .
F F3 0.05259(19) -0.13151(11) 0.05246(11) 0.0747(5) Uani d . 1 . .
F F4 0.1158(2) -0.22673(10) 0.27230(11) 0.0775(5) Uani d . 1 . .
F F5 0.2745(2) -0.22093(10) 0.17918(11) 0.0736(5) Uani d . 1 . .
F F6 0.3482(2) -0.13628(10) 0.29418(11) 0.0664(5) Uani 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
O1 C1 O2 . . 123.7(3) ?
O1 C1 C2 . . 120.3(3) ?
O2 C1 C2 . . 115.9(3) ?
C7 C2 C3 . . 118.5(3) ?
C7 C2 C1 . . 121.4(3) ?
C3 C2 C1 . . 119.9(3) ?
C2 C3 C4 . . 119.9(2) ?
C2 C3 H3 . . 120.0 ?
C4 C3 H3 . . 120.0 ?
C5 C4 C3 . . 121.5(2) ?
C5 C4 H4 . . 119.2 ?
C3 C4 H4 . . 119.2 ?
C4 C5 C6 . . 118.1(2) ?
C4 C5 C8 . . 119.1(2) ?
C6 C5 C8 . . 122.8(2) ?
C7 C6 C5 . . 120.2(3) ?
C7 C6 H6 . . 119.9 ?
C5 C6 H6 . . 119.9 ?
C6 C7 C2 . . 121.6(2) ?
C6 C7 H7 . . 119.2 ?
C2 C7 H7 . . 119.2 ?
C10 C8 C11 . . 105.3(2) ?
C10 C8 C9 . . 108.2(2) ?
C11 C8 C9 . . 112.9(2) ?
C10 C8 C5 . . 113.1(2) ?
C11 C8 C5 . . 111.55(19) ?
C9 C8 C5 . . 105.9(2) ?
F4 C9 F6 . . 106.7(3) ?
F4 C9 F5 . . 106.3(2) ?
F6 C9 F5 . . 106.7(2) ?
F4 C9 C8 . . 111.7(2) ?
F6 C9 C8 . . 111.0(2) ?
F5 C9 C8 . . 114.0(3) ?
F1 C10 F3 . . 106.3(3) ?
F1 C10 F2 . . 106.5(2) ?
F3 C10 F2 . . 106.1(2) ?
F1 C10 C8 . . 111.9(2) ?
F3 C10 C8 . . 111.6(2) ?
F2 C10 C8 . . 113.9(2) ?
C16 C11 C12 . . 117.4(2) ?
C16 C11 C8 . . 123.4(2) ?
C12 C11 C8 . . 119.0(2) ?
C13 C12 C11 . . 121.4(2) ?
C13 C12 H12 . . 119.3 ?
C11 C12 H12 . . 119.3 ?
C14 C13 C12 . . 120.3(2) ?
C14 C13 H13 . . 119.9 ?
C12 C13 H13 . . 119.9 ?
C13 C14 C15 . . 118.9(2) ?
C13 C14 C17 . . 121.5(2) ?
C15 C14 C17 . . 119.5(2) ?
C14 C15 C16 . . 120.6(2) ?
C14 C15 H15 . . 119.7 ?
C16 C15 H15 . . 119.7 ?
C11 C16 C15 . . 121.3(2) ?
C11 C16 H16 . . 119.3 ?
C15 C16 H16 . . 119.3 ?
O4 C17 O3 . . 123.8(3) ?
O4 C17 C14 . . 120.6(3) ?
O3 C17 C14 . . 115.6(3) ?
C1 O2 H2A . . 109.5 ?
C17 O3 H3A . . 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
C1 O1 . 1.246(3) ?
C1 O2 . 1.283(3) ?
C1 C2 . 1.477(3) ?
C2 C7 . 1.377(3) ?
C2 C3 . 1.379(3) ?
C3 C4 . 1.380(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.380(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.383(3) ?
C5 C8 . 1.544(3) ?
C6 C7 . 1.374(3) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C10 . 1.530(3) ?
C8 C11 . 1.532(3) ?
C8 C9 . 1.538(3) ?
C9 F4 . 1.331(3) ?
C9 F6 . 1.333(3) ?
C9 F5 . 1.340(3) ?
C10 F1 . 1.333(3) ?
C10 F3 . 1.332(3) ?
C10 F2 . 1.341(3) ?
C11 C16 . 1.379(3) ?
C11 C12 . 1.393(3) ?
C12 C13 . 1.378(3) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.375(3) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.379(3) ?
C14 C17 . 1.479(3) ?
C15 C16 . 1.377(3) ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
C17 O4 . 1.254(3) ?
C17 O3 . 1.276(3) ?
O2 H2A . 0.8200 ?
O3 H3A . 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
O2 H2A O4 4_466 0.82 1.85 2.661(2) 169
O3 H3A O1 4_665 0.82 1.80 2.603(2) 165
C15 H15 F1 1_655 0.93 2.48 3.382(3) 163
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
O1 C1 C2 C7 . . . . -174.9(2) ?
O2 C1 C2 C7 . . . . 2.1(4) ?
O1 C1 C2 C3 . . . . 1.2(4) ?
O2 C1 C2 C3 . . . . 178.2(2) ?
C7 C2 C3 C4 . . . . 2.2(4) ?
C1 C2 C3 C4 . . . . -173.9(2) ?
C2 C3 C4 C5 . . . . 0.1(4) ?
C3 C4 C5 C6 . . . . -3.0(4) ?
C3 C4 C5 C8 . . . . 179.2(2) ?
C4 C5 C6 C7 . . . . 3.6(4) ?
C8 C5 C6 C7 . . . . -178.7(2) ?
C5 C6 C7 C2 . . . . -1.3(4) ?
C3 C2 C7 C6 . . . . -1.6(4) ?
C1 C2 C7 C6 . . . . 174.5(3) ?
C4 C5 C8 C10 . . . . -159.9(2) ?
C6 C5 C8 C10 . . . . 22.4(3) ?
C4 C5 C8 C11 . . . . -41.5(3) ?
C6 C5 C8 C11 . . . . 140.9(2) ?
C4 C5 C8 C9 . . . . 81.7(3) ?
C6 C5 C8 C9 . . . . -95.9(3) ?
C10 C8 C9 F4 . . . . -73.2(3) ?
C11 C8 C9 F4 . . . . 170.6(2) ?
C5 C8 C9 F4 . . . . 48.3(3) ?
C10 C8 C9 F6 . . . . 167.9(2) ?
C11 C8 C9 F6 . . . . 51.7(3) ?
C5 C8 C9 F6 . . . . -70.7(3) ?
C10 C8 C9 F5 . . . . 47.3(3) ?
C11 C8 C9 F5 . . . . -68.9(3) ?
C5 C8 C9 F5 . . . . 168.8(2) ?
C11 C8 C10 F1 . . . . -70.1(3) ?
C9 C8 C10 F1 . . . . 168.9(2) ?
C5 C8 C10 F1 . . . . 51.9(3) ?
C11 C8 C10 F3 . . . . 48.8(3) ?
C9 C8 C10 F3 . . . . -72.2(3) ?
C5 C8 C10 F3 . . . . 170.8(2) ?
C11 C8 C10 F2 . . . . 169.0(2) ?
C9 C8 C10 F2 . . . . 48.0(3) ?
C5 C8 C10 F2 . . . . -69.0(3) ?
C10 C8 C11 C16 . . . . -94.9(3) ?
C9 C8 C11 C16 . . . . 22.9(4) ?
C5 C8 C11 C16 . . . . 142.0(2) ?
C10 C8 C11 C12 . . . . 80.3(3) ?
C9 C8 C11 C12 . . . . -161.9(2) ?
C5 C8 C11 C12 . . . . -42.7(3) ?
C16 C11 C12 C13 . . . . 0.6(4) ?
C8 C11 C12 C13 . . . . -174.9(2) ?
C11 C12 C13 C14 . . . . -1.1(4) ?
C12 C13 C14 C15 . . . . 0.1(4) ?
C12 C13 C14 C17 . . . . 179.3(2) ?
C13 C14 C15 C16 . . . . 1.3(4) ?
C17 C14 C15 C16 . . . . -177.8(3) ?
C12 C11 C16 C15 . . . . 0.9(4) ?
C8 C11 C16 C15 . . . . 176.1(3) ?
C14 C15 C16 C11 . . . . -1.9(4) ?
C13 C14 C17 O4 . . . . -8.7(4) ?
C15 C14 C17 O4 . . . . 170.4(3) ?
C13 C14 C17 O3 . . . . 171.5(3) ?
C15 C14 C17 O3 . . . . -9.4(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 550186
