#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/99/2209992.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_2209992
loop_
_publ_author_name
'Rodríguez de Barbarín, Cecilia'
'Bernès, Sylvain'
'Macossay, Javier'
'Cassidy, Patrick E.'
_publ_section_title
;
 4,4'-(1,1,1,3,3,3-Hexafluoropropane-2,2-diyl)bis(benzoyl chloride)
;
_journal_coeditor_code           SA2010
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3602
_journal_page_last               o3603
_journal_paper_doi               10.1107/S1600536806028236
_journal_volume                  62
_journal_year                    2006
_chemical_formula_moiety         'C17 H8 Cl2 F6 O2'
_chemical_formula_sum            'C17 H8 Cl2 F6 O2'
_chemical_formula_weight         429.13
_chemical_melting_point          416
_chemical_name_common
;
2,2-Bis(4-chloroformylbenzyl)-1,1,1,3,3,3-hexafluoropropane
;
_chemical_name_systematic
;
4,4'-(1,1,1,3,3,3-Hexafluoropropane-2,2-diyl)bis(benzoyl chloride)
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL-Plus
_cell_angle_alpha                90.00
_cell_angle_beta                 98.12(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   19.338(9)
_cell_length_b                   12.299(4)
_cell_length_c                   14.677(4)
_cell_measurement_reflns_used    56
_cell_measurement_temperature    298.0(10)
_cell_measurement_theta_max      12.375
_cell_measurement_theta_min      4.670
_cell_volume                     3456(2)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    SHELXTL-Plus
_computing_publication_material  SHELXTL-Plus
_computing_structure_refinement  SHELXTL-Plus
_computing_structure_solution    'SHELXTL-Plus (Sheldrick, 1997)'
_diffrn_ambient_temperature      298.0(10)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       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  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0402
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3727
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.13
_diffrn_standards_decay_%        6.4
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.447
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.414
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3122
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.1170
_refine_ls_R_factor_gt           0.0639
_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)+(0.0714P)²+9.4954P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1534
_refine_ls_wR_factor_ref         0.1955
_reflns_number_gt                1830
_reflns_number_total             3122
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sa2010.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2209992
_cod_database_fobs_code          2209992
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
C C1 0.7100(3) 0.3099(5) 0.3006(4) 0.0761(15) Uani d . 1
C C2 0.7030(2) 0.3310(3) 0.1969(3) 0.0535(10) Uani d . 1
C C3 0.7038(2) 0.2199(4) 0.1463(4) 0.0680(13) Uani d . 1
C C4 0.6335(2) 0.3917(3) 0.1701(3) 0.0504(10) Uani d . 1
C C5 0.5709(2) 0.3407(4) 0.1397(3) 0.0618(12) Uani d . 1
H H5A 0.5698 0.2655 0.1333 0.074 Uiso calc R 1
C C6 0.5099(2) 0.3990(4) 0.1187(3) 0.0629(12) Uani d . 1
H H6A 0.4683 0.3632 0.0982 0.075 Uiso calc R 1
C C7 0.5105(2) 0.5109(4) 0.1281(3) 0.0559(11) Uani d . 1
C C8 0.5721(2) 0.5627(4) 0.1603(3) 0.0584(11) Uani d . 1
H H8A 0.5729 0.6378 0.1674 0.070 Uiso calc R 1
C C9 0.6327(2) 0.5038(4) 0.1820(3) 0.0577(11) Uani d . 1
H H9A 0.6738 0.5397 0.2050 0.069 Uiso calc R 1
C C10 0.4426(2) 0.5677(5) 0.1025(3) 0.0677(13) Uani d . 1
C C11 0.7653(2) 0.3956(3) 0.1689(3) 0.0509(10) Uani d . 1
C C12 0.8292(2) 0.4053(4) 0.2261(3) 0.0652(12) Uani d . 1
H H12A 0.8353 0.3736 0.2842 0.078 Uiso calc R 1
C C13 0.8832(2) 0.4626(4) 0.1956(4) 0.0658(13) Uani d . 1
H H13A 0.9258 0.4682 0.2334 0.079 Uiso calc R 1
C C14 0.8749(2) 0.5110(4) 0.1106(4) 0.0632(12) Uani d . 1
C C15 0.8115(2) 0.5006(4) 0.0545(3) 0.0632(12) Uani d . 1
H H15A 0.8053 0.5326 -0.0035 0.076 Uiso calc R 1
C C16 0.7578(2) 0.4436(4) 0.0835(3) 0.0590(11) Uani d . 1
H H16A 0.7155 0.4373 0.0448 0.071 Uiso calc R 1
C C17 0.9346(3) 0.5727(5) 0.0860(5) 0.0878(17) Uani d . 1
O O1 0.38988(18) 0.5265(4) 0.0704(3) 0.0918(12) Uani d . 1
O O2 0.9919(2) 0.5810(4) 0.1262(4) 0.131(2) Uani d . 1
F F1 0.76061(17) 0.2385(3) 0.3309(2) 0.0973(11) Uani d . 1
F F2 0.65087(17) 0.2690(3) 0.3244(2) 0.0967(10) Uani d . 1
F F3 0.72308(16) 0.4012(3) 0.3479(2) 0.0861(9) Uani d . 1
F F4 0.76753(15) 0.1775(2) 0.1554(2) 0.0887(10) Uani d . 1
F F5 0.66239(16) 0.1456(2) 0.1762(3) 0.0958(11) Uani d . 1
F F6 0.68282(15) 0.2318(2) 0.0564(2) 0.0791(8) Uani d . 1
Cl Cl1 0.44406(8) 0.70990(13) 0.12276(12) 0.0931(5) Uani d . 1
Cl Cl2 0.92003(11) 0.6431(2) -0.01868(14) 0.1394(9) 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'
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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
1 3 -2
-8 4 -3
-4 4 7
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
C1 C2 C3 108.6(4) ?
C1 C2 C4 106.7(4) ?
C1 C2 C11 112.9(4) yes
C4 C2 C3 111.8(4) ?
C4 C2 C11 111.6(3) ?
C11 C2 C3 105.2(3) yes
F3 C1 F2 106.7(5) ?
F3 C1 F1 107.7(5) ?
F2 C1 F1 106.1(4) ?
F3 C1 C2 111.1(4) ?
F2 C1 C2 111.4(4) ?
F1 C1 C2 113.4(5) ?
F4 C3 F5 106.9(4) ?
F4 C3 F6 106.9(4) ?
F5 C3 F6 106.8(4) ?
F4 C3 C2 111.7(4) ?
F5 C3 C2 113.5(4) ?
F6 C3 C2 110.7(4) ?
C5 C4 C9 117.8(4) ?
C5 C4 C2 123.8(4) ?
C9 C4 C2 118.3(4) ?
C6 C5 C4 121.3(4) ?
C5 C6 C7 120.1(4) ?
C8 C7 C6 119.3(4) ?
C8 C7 C10 124.1(4) ?
C6 C7 C10 116.6(4) ?
C7 C8 C9 120.3(4) ?
C8 C9 C4 121.2(4) ?
O1 C10 C7 125.7(5) ?
O1 C10 Cl1 118.9(4) ?
C7 C10 Cl1 115.3(4) ?
C16 C11 C12 118.9(4) ?
C16 C11 C2 118.5(4) ?
C12 C11 C2 122.6(4) ?
C13 C12 C11 119.4(5) ?
C14 C13 C12 121.3(4) ?
C13 C14 C15 118.8(4) ?
C13 C14 C17 117.0(5) ?
C15 C14 C17 124.2(5) ?
C16 C15 C14 120.7(5) ?
C15 C16 C11 121.0(4) ?
O2 C17 C14 129.4(6) ?
O2 C17 Cl2 114.7(5) ?
C14 C17 Cl2 115.9(4) ?
C10 Cl1 Cl2 82.75(16) ?
C17 Cl2 Cl1 83.97(19) ?
C6 C5 H5A 119.4 ?
C4 C5 H5A 119.4 ?
C5 C6 H6A 119.9 ?
C7 C6 H6A 119.9 ?
C7 C8 H8A 119.9 ?
C9 C8 H8A 119.9 ?
C8 C9 H9A 119.4 ?
C4 C9 H9A 119.4 ?
C13 C12 H12A 120.3 ?
C11 C12 H12A 120.3 ?
C14 C13 H13A 119.4 ?
C12 C13 H13A 119.4 ?
C16 C15 H15A 119.7 ?
C14 C15 H15A 119.7 ?
C15 C16 H16A 119.5 ?
C11 C16 H16A 119.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C10 O1 1.176(6) yes
C10 Cl1 1.774(6) yes
C17 O2 1.184(7) yes
C17 Cl2 1.751(7) yes
C1 F3 1.326(7) yes
C1 F2 1.339(6) yes
C1 F1 1.343(6) yes
C1 C2 1.531(7) ?
C2 C4 1.539(6) ?
C2 C11 1.547(6) ?
C2 C3 1.556(7) ?
C3 F4 1.327(5) yes
C3 F5 1.330(5) yes
C3 F6 1.333(6) yes
C4 C5 1.381(6) ?
C4 C9 1.390(6) ?
C5 C6 1.377(6) ?
C6 C7 1.383(7) ?
C7 C8 1.374(6) ?
C7 C10 1.488(6) ?
C8 C9 1.375(6) ?
C11 C16 1.374(6) ?
C11 C12 1.397(6) ?
C12 C13 1.386(7) ?
C13 C14 1.370(7) ?
C14 C15 1.383(6) ?
C14 C17 1.469(7) ?
C15 C16 1.371(6) ?
C5 H5A 0.9300 ?
C6 H6A 0.9300 ?
C8 H8A 0.9300 ?
C9 H9A 0.9300 ?
C12 H12A 0.9300 ?
C13 H13A 0.9300 ?
C15 H15A 0.9300 ?
C16 H16A 0.9300 ?
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
F3 C1 C2 C4 -71.4(5)
F2 C1 C2 C4 47.5(6)
F1 C1 C2 C4 167.1(4)
F3 C1 C2 C11 51.6(5)
F2 C1 C2 C11 170.4(4)
F1 C1 C2 C11 -69.9(6)
F3 C1 C2 C3 167.9(4)
F2 C1 C2 C3 -73.2(5)
F1 C1 C2 C3 46.4(6)
C1 C2 C3 F4 -74.5(5)
C4 C2 C3 F4 167.9(4)
C11 C2 C3 F4 46.6(5)
C1 C2 C3 F5 46.4(5)
C4 C2 C3 F5 -71.1(5)
C11 C2 C3 F5 167.6(4)
C1 C2 C3 F6 166.4(4)
C4 C2 C3 F6 48.9(5)
C11 C2 C3 F6 -72.4(4)
C1 C2 C4 C5 -92.4(5)
C11 C2 C4 C5 143.8(4)
C3 C2 C4 C5 26.2(6)
C1 C2 C4 C9 83.7(5)
C11 C2 C4 C9 -40.0(5)
C3 C2 C4 C9 -157.6(4)
C9 C4 C5 C6 2.2(7)
C2 C4 C5 C6 178.4(4)
C4 C5 C6 C7 -0.2(7)
C5 C6 C7 C8 -1.3(7)
C5 C6 C7 C10 179.0(4)
C6 C7 C8 C9 0.7(7)
C10 C7 C8 C9 -179.7(4)
C7 C8 C9 C4 1.4(7)
C5 C4 C9 C8 -2.9(7)
C2 C4 C9 C8 -179.3(4)
C8 C7 C10 O1 175.9(5)
C6 C7 C10 O1 -4.5(7)
C8 C7 C10 Cl1 -3.8(6)
C6 C7 C10 Cl1 175.9(4)
C1 C2 C11 C16 -163.6(4)
C4 C2 C11 C16 -43.4(5)
C3 C2 C11 C16 78.0(5)
C1 C2 C11 C12 17.6(6)
C4 C2 C11 C12 137.8(4)
C3 C2 C11 C12 -100.8(5)
C16 C11 C12 C13 -0.2(7)
C2 C11 C12 C13 178.6(4)
C11 C12 C13 C14 0.8(7)
C12 C13 C14 C15 -1.0(7)
C12 C13 C14 C17 178.1(5)
C13 C14 C15 C16 0.5(7)
C17 C14 C15 C16 -178.5(5)
C14 C15 C16 C11 0.1(7)
C12 C11 C16 C15 -0.3(7)
C2 C11 C16 C15 -179.1(4)
C13 C14 C17 O2 6.1(10)
C15 C14 C17 O2 -174.9(7)
C13 C14 C17 Cl2 -174.8(4)
C15 C14 C17 Cl2 4.2(7)
C7 C10 O1 O2 -36.8(4)
Cl1 C10 O1 O2 142.8(8)
C14 C17 O2 O1 -39.5(6)
Cl2 C17 O2 O1 141.3(11)
C10 O1 O2 C17 -136.2(11)
O1 C10 Cl1 Cl2 -147.3(4)
C7 C10 Cl1 Cl2 32.3(3)
O2 C17 Cl2 Cl1 -149.1(6)
C14 C17 Cl2 Cl1 31.6(4)
C10 Cl1 Cl2 C17 -68.8(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2109582
2 PubChem 2831813
