#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/59/7035972.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_7035972
loop_
_publ_author_name
'Brisdon, Alan K.'
'Ali Ghaba, Hana'
'Beutel, Bernd'
'Egjandi, Amina'
'Addaraidi, Arij'
'Pritchard, Robin G.'
_publ_section_title
;
 Perfluoropropenyl-containing phosphines from HFC replacements.
;
_journal_issue                   45
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              19717
_journal_page_last               19731
_journal_paper_doi               10.1039/c5dt02043c
_journal_volume                  44
_journal_year                    2015
_chemical_formula_moiety         'C14 H4 F20 O2 P2'
_chemical_formula_sum            'C14 H4 F20 O2 P2'
_chemical_formula_weight         646.11
_chemical_name_systematic        (CF3CF=CF)2P(O)CH2CH2P(O)(CF=CFCF3)2
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2015-05-20T00:58:02-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2015-07-08 deposited with the CCDC.
2015-07-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.70(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.566(6)
_cell_length_b                   5.0981(8)
_cell_length_c                   16.835(4)
_cell_measurement_reflns_used    356
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      17.55
_cell_measurement_theta_min      3.42
_cell_measurement_wavelength     0.7107
_cell_volume                     2048.4(8)
_computing_cell_refinement
'CrysalisPro  Version 1.171.36.28a (Agilent Technologies, 2013)'
_computing_data_collection
'CrysalisPro  Version 1.171.36.28a (Agilent Technologies, 2013)'
_computing_data_reduction
'CrysalisPro  Version 1.171.36.28a (Agilent Technologies, 2013)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'Platon (Spek 2105)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SIR-92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.34
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type
'Agilent Technologies Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.00585
_diffrn_orient_matrix_UB_12      0.01102
_diffrn_orient_matrix_UB_13      0.039458
_diffrn_orient_matrix_UB_21      -0.013714
_diffrn_orient_matrix_UB_22      0.058407
_diffrn_orient_matrix_UB_23      -0.017889
_diffrn_orient_matrix_UB_31      -0.069551
_diffrn_orient_matrix_UB_32      0.000244
_diffrn_orient_matrix_UB_33      -0.001944
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2594
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6352
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_reduction_process
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26
_diffrn_reflns_theta_min         3.337
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.406
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
        (compiled Mar 18 2013,11:47:30)
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.095
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.518
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.118
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.941
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2018
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.941
_refine_ls_R_factor_all          0.2709
_refine_ls_R_factor_gt           0.0932
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0187P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1343
_refine_ls_wR_factor_ref         0.2112
_reflns_number_gt                625
_reflns_number_total             2018
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5dt02043c1.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7035966--7035973.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7035972
#BEGIN Tags that were not found in dictionaries:
_shelx_estimated_absorpt_t_min   0.923
_shelx_estimated_absorpt_t_max   0.98
#END Tags that were not found in dictionaries
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
C1 C 0.7320(4) 0.1928(17) 0.5264(6) 0.033(3) Uani 1 d
H1A H 0.7524 0.2037 0.5845 0.04 Uiso 1 calc
H1B H 0.7248 0.0054 0.5125 0.04 Uiso 1 calc
C2 C 0.6263(4) 0.2435(17) 0.4129(6) 0.030(3) Uani 1 d
C3 C 0.5778(5) 0.3186(18) 0.3690(6) 0.032(3) Uani 1 d
C4 C 0.5357(5) 0.507(2) 0.3921(7) 0.046(3) Uani 1 d
C5 C 0.6284(5) 0.2285(18) 0.5853(6) 0.034(3) Uani 1 d
C6 C 0.6331(4) 0.2973(19) 0.6600(7) 0.034(3) Uani 1 d
C7 C 0.6754(5) 0.478(2) 0.7117(7) 0.039(3) Uani 1 d
F1 F 0.6546(2) 0.0625(10) 0.3786(3) 0.0437(17) Uani 1 d
F2 F 0.5586(2) 0.2280(11) 0.2930(4) 0.0504(18) Uani 1 d
F3 F 0.5306(3) 0.7169(12) 0.3459(4) 0.067(2) Uani 1 d
F4 F 0.5526(3) 0.5707(10) 0.4698(4) 0.0463(18) Uani 1 d
F5 F 0.4858(3) 0.3893(11) 0.3802(4) 0.0523(18) Uani 1 d
F6 F 0.5875(3) 0.0584(10) 0.5512(3) 0.0419(17) Uani 1 d
F7 F 0.5975(3) 0.2036(10) 0.7034(3) 0.0455(18) Uani 1 d
F8 F 0.6562(3) 0.7260(11) 0.7107(4) 0.057(2) Uani 1 d
F9 F 0.6877(3) 0.4082(11) 0.7890(4) 0.056(2) Uani 1 d
F10 F 0.7228(3) 0.4890(10) 0.6879(4) 0.0463(17) Uani 1 d
O1 O 0.6711(3) 0.6508(11) 0.5189(4) 0.0386(19) Uani 1 d
P1 P 0.66677(13) 0.3618(5) 0.51257(18) 0.0358(8) Uani 1 d
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 '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_site_symmetry_1
C1 C1 P1 111.7(8) 7_656
C1 C1 H1A 109.3 7_656
P1 C1 H1A 109.3 .
C1 C1 H1B 109.3 7_656
P1 C1 H1B 109.3 .
H1A C1 H1B 107.9 .
C3 C2 F1 116.7(10) .
C3 C2 P1 130.2(9) .
F1 C2 P1 112.9(7) .
C2 C3 F2 120.6(10) .
C2 C3 C4 128.6(10) .
F2 C3 C4 110.8(9) .
F3 C4 F4 110.5(10) .
F3 C4 F5 108.7(10) .
F4 C4 F5 108.9(10) .
F3 C4 C3 109.7(9) .
F4 C4 C3 109.6(10) .
F5 C4 C3 109.4(9) .
C6 C5 F6 118.4(9) .
C6 C5 P1 127.5(9) .
F6 C5 P1 113.7(7) .
C5 C6 F7 120.9(10) .
C5 C6 C7 128.6(11) .
F7 C6 C7 110.5(9) .
F9 C7 F10 107.5(10) .
F9 C7 F8 105.2(8) .
F10 C7 F8 106.6(10) .
F9 C7 C6 112.0(10) .
F10 C7 C6 113.0(9) .
F8 C7 C6 112.0(9) .
O1 P1 C1 115.1(4) .
O1 P1 C2 114.0(4) .
C1 P1 C2 103.6(5) .
O1 P1 C5 111.0(4) .
C1 P1 C5 108.7(4) .
C2 P1 C5 103.6(5) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C1 1.510(17) 7_656
C1 P1 1.786(10) .
C1 H1A 0.99 .
C1 H1B 0.99 .
C2 C3 1.303(13) .
C2 F1 1.363(10) .
C2 P1 1.838(11) .
C3 F2 1.337(10) .
C3 C4 1.527(15) .
C4 F3 1.313(11) .
C4 F4 1.316(12) .
C4 F5 1.335(13) .
C5 C6 1.285(12) .
C5 F6 1.349(10) .
C5 P1 1.842(10) .
C6 F7 1.353(11) .
C6 C7 1.501(14) .
C7 F9 1.313(11) .
C7 F10 1.318(12) .
C7 F8 1.350(11) .
O1 P1 1.479(6) .
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
_geom_torsion_site_symmetry_1
F1 C2 C3 F2 -2.7(14) .
P1 C2 C3 F2 171.8(7) .
F1 C2 C3 C4 176.9(9) .
P1 C2 C3 C4 -8.6(17) .
C2 C3 C4 F3 115.1(12) .
F2 C3 C4 F3 -65.3(12) .
C2 C3 C4 F4 -6.5(16) .
F2 C3 C4 F4 173.2(8) .
C2 C3 C4 F5 -125.8(12) .
F2 C3 C4 F5 53.9(11) .
F6 C5 C6 F7 -0.7(15) .
P1 C5 C6 F7 172.1(7) .
F6 C5 C6 C7 178.7(9) .
P1 C5 C6 C7 -8.5(17) .
C5 C6 C7 F9 -147.3(11) .
F7 C6 C7 F9 32.1(12) .
C5 C6 C7 F10 -25.8(16) .
F7 C6 C7 F10 153.7(8) .
C5 C6 C7 F8 94.7(13) .
F7 C6 C7 F8 -85.8(11) .
C1 C1 P1 O1 -50.0(11) 7_656
C1 C1 P1 C2 75.1(10) 7_656
C1 C1 P1 C5 -175.2(9) 7_656
C3 C2 P1 O1 -47.3(12) .
F1 C2 P1 O1 127.4(6) .
C3 C2 P1 C1 -173.1(10) .
F1 C2 P1 C1 1.6(7) .
C3 C2 P1 C5 73.5(11) .
F1 C2 P1 C5 -111.8(7) .
C6 C5 P1 O1 -42.2(11) .
F6 C5 P1 O1 131.0(7) .
C6 C5 P1 C1 85.4(11) .
F6 C5 P1 C1 -101.5(8) .
C6 C5 P1 C2 -164.9(10) .
F6 C5 P1 C2 8.2(8) .
