#------------------------------------------------------------------------------
#$Date: 2016-03-25 09:28:39 +0200 (Fri, 25 Mar 2016) $
#$Revision: 179724 $
#$URL: svn://www.crystallography.net/cod/cif/7/00/24/7002429.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_7002429
loop_
_publ_author_name
'Abdalilah, Mohammed'
'Zurawinski, Remigiuz'
'Canac, Yves'
'Laleu, Benoît'
'Lacour, Jérôme'
'Lepetit, Christine'
'Magro, Germinal'
'Bernardinelli, Gérald'
'Donnadieu, Bruno'
'Duhayon, Carine'
'Mikolajczyk, Marian'
'Chauvin, Remi'
_publ_section_title
;
 Vicinal diphosphoniums: electrostatic repulsion under covalent
 constraint
;
_journal_issue                   40
_journal_name_full               'Dalton Transactions'
_journal_page_first              8493
_journal_page_last               8508
_journal_paper_doi               10.1039/b903933c
_journal_year                    2009
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C32 H29 O P2, C4 H8 O, F6 P'
_chemical_formula_sum            'C36 H37 F6 O2 P3'
_chemical_formula_weight         708.57
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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
_cell_angle_alpha                110.218(5)
_cell_angle_beta                 113.218(5)
_cell_angle_gamma                91.949(5)
_cell_formula_units_Z            2
_cell_length_a                   11.474(5)
_cell_length_b                   12.913(5)
_cell_length_c                   13.705(5)
_cell_measurement_reflns_used    8000
_cell_measurement_temperature    180
_cell_measurement_theta_max      26.05
_cell_measurement_theta_min      1.65
_cell_measurement_wavelength     0.71073
_cell_volume                     1716.7(12)
_computing_cell_refinement       'Stoe IPDS software (Stoe, 1996)'
_computing_data_collection       'Stoe IPDS software (Stoe, 1996)'
_computing_data_reduction        'XRED (Stoe, 1.08, 1996)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      180
_diffrn_measured_fraction_theta_full 0.916
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measurement_device       'Stoe IPDS'
_diffrn_measurement_method       φ
_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  0.0395
_diffrn_reflns_av_unetI/netI     0.046
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17048
_diffrn_reflns_theta_full        26.17
_diffrn_reflns_theta_max         26.17
_diffrn_reflns_theta_min         2.34
_diffrn_standards_decay_%        0.1
_diffrn_standards_interval_time  4
_diffrn_standards_number         200
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_correction_T_min  0.918
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details
;
(See: Walker, N. & Stuart, D. (1983) Acta Cryst. A39, 158-166)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.375
_exptl_crystal_size_mid          0.375
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.616
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     421
_refine_ls_number_reflns         6294
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0558
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1015P)²+0.1144P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.151
_refine_ls_wR_factor_ref         0.1656
_reflns_number_gt                4325
_reflns_number_total             6294
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b903933c.txt
_cod_data_source_block           compound13
_cod_database_code               7002429
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.3706(3) 0.0562(2) 0.2319(3) 0.0381(7) Uani 1 1 d . . .
C2 C 1.4069(4) -0.0484(3) 0.1972(3) 0.0526(9) Uani 1 1 d . . .
H2 H 1.369 -0.0969 0.1199 0.063 Uiso 1 1 calc R . .
C3 C 1.4983(4) -0.0790(3) 0.2774(4) 0.0603(10) Uani 1 1 d . . .
H3 H 1.5218 -0.1484 0.2537 0.072 Uiso 1 1 calc R . .
C4 C 1.5558(4) -0.0087(3) 0.3924(3) 0.0540(9) Uani 1 1 d . . .
H4 H 1.6169 -0.0307 0.446 0.065 Uiso 1 1 calc R . .
C5 C 1.5217(3) 0.0956(3) 0.4277(3) 0.0500(8) Uani 1 1 d . . .
H5 H 1.5613 0.144 0.5051 0.06 Uiso 1 1 calc R . .
C6 C 1.4291(3) 0.1275(3) 0.3483(3) 0.0437(7) Uani 1 1 d . . .
H6 H 1.4057 0.1968 0.3727 0.052 Uiso 1 1 calc R . .
C7 C 1.3276(3) 0.1689(3) 0.0746(3) 0.0387(7) Uani 1 1 d . . .
C8 C 1.4203(3) 0.2655(3) 0.1474(3) 0.0458(7) Uani 1 1 d . . .
H8 H 1.4435 0.2934 0.2262 0.055 Uiso 1 1 calc R . .
C9 C 1.4794(3) 0.3215(3) 0.1037(3) 0.0534(8) Uani 1 1 d . . .
H9 H 1.5422 0.3866 0.1529 0.064 Uiso 1 1 calc R . .
C10 C 1.4443(4) 0.2798(3) -0.0135(3) 0.0559(9) Uani 1 1 d . . .
H10 H 1.485 0.3166 -0.0426 0.067 Uiso 1 1 calc R . .
C11 C 1.3510(4) 0.1857(4) -0.0871(3) 0.0624(10) Uani 1 1 d . . .
H11 H 1.3268 0.1596 -0.1659 0.075 Uiso 1 1 calc R . .
C12 C 1.2924(4) 0.1293(3) -0.0442(3) 0.0538(9) Uani 1 1 d . . .
H12 H 1.2291 0.0646 -0.0943 0.065 Uiso 1 1 calc R . .
C13 C 1.1639(3) 0.1786(3) 0.1912(3) 0.0390(7) Uani 1 1 d . . .
H13A H 1.1217 0.1384 0.2203 0.047 Uiso 1 1 calc R . .
H13B H 1.2265 0.2426 0.2565 0.047 Uiso 1 1 calc R . .
C14 C 1.0635(3) 0.2205(2) 0.1097(2) 0.0355(6) Uani 1 1 d . . .
H14A H 0.999 0.1566 0.046 0.043 Uiso 1 1 calc R . .
H14B H 1.1052 0.2579 0.0782 0.043 Uiso 1 1 calc R . .
C15 C 1.1046(3) 0.4344(2) 0.2994(2) 0.0328(6) Uani 1 1 d . . .
C16 C 1.0885(3) 0.4897(3) 0.3987(3) 0.0437(7) Uani 1 1 d . . .
H16 H 1.0149 0.4658 0.4043 0.052 Uiso 1 1 calc R . .
C17 C 1.1813(3) 0.5798(3) 0.4890(3) 0.0537(8) Uani 1 1 d . . .
H17 H 1.1699 0.6164 0.5552 0.064 Uiso 1 1 calc R . .
C18 C 1.2902(4) 0.6155(3) 0.4815(3) 0.0572(9) Uani 1 1 d . . .
H18 H 1.3531 0.6757 0.543 0.069 Uiso 1 1 calc R . .
C19 C 1.3065(3) 0.5624(3) 0.3830(4) 0.0622(10) Uani 1 1 d . . .
H19 H 1.38 0.5874 0.3778 0.075 Uiso 1 1 calc R . .
C20 C 1.2138(3) 0.4719(3) 0.2916(3) 0.0479(8) Uani 1 1 d . . .
H20 H 1.2249 0.4363 0.225 0.057 Uiso 1 1 calc R . .
C21 C 0.9032(3) 0.2464(2) 0.2357(2) 0.0328(6) Uani 1 1 d . . .
C22 C 0.9751(3) 0.2241(3) 0.3321(3) 0.0390(7) Uani 1 1 d . . .
H22 H 1.0642 0.2499 0.3709 0.047 Uiso 1 1 calc R . .
C23 C 0.9142(4) 0.1636(3) 0.3703(3) 0.0516(8) Uani 1 1 d . . .
H23 H 0.9621 0.1482 0.4346 0.062 Uiso 1 1 calc R . .
C24 C 0.7812(4) 0.1260(3) 0.3123(3) 0.0563(9) Uani 1 1 d . . .
H24 H 0.7401 0.0849 0.3377 0.068 Uiso 1 1 calc R . .
C25 C 0.7103(3) 0.1487(3) 0.2186(3) 0.0531(9) Uani 1 1 d . . .
H25 H 0.6211 0.1235 0.1808 0.064 Uiso 1 1 calc R . .
C26 C 0.7702(3) 0.2094(3) 0.1788(3) 0.0420(7) Uani 1 1 d . . .
H26 H 0.7215 0.2249 0.1147 0.05 Uiso 1 1 calc R . .
C27 C 0.8708(3) 0.3657(2) 0.0821(2) 0.0381(6) Uani 1 1 d . . .
C28 C 0.8258(4) 0.3094(3) -0.0358(3) 0.0596(10) Uani 1 1 d . . .
H28 H 0.855 0.2448 -0.0654 0.072 Uiso 1 1 calc R . .
C29 C 0.7375(4) 0.3495(4) -0.1094(3) 0.0696(11) Uani 1 1 d . . .
H29 H 0.7089 0.3122 -0.1886 0.083 Uiso 1 1 calc R . .
C30 C 0.6915(4) 0.4424(3) -0.0685(3) 0.0615(10) Uani 1 1 d . . .
H30 H 0.6337 0.4695 -0.1191 0.074 Uiso 1 1 calc R . .
C31 C 0.7317(4) 0.4966(3) 0.0499(4) 0.0667(11) Uani 1 1 d . . .
H31 H 0.6979 0.5584 0.0783 0.08 Uiso 1 1 calc R . .
C32 C 0.8211(4) 0.4593(3) 0.1249(3) 0.0563(9) Uani 1 1 d . . .
H32 H 0.8485 0.4963 0.204 0.068 Uiso 1 1 calc R . .
O2A O 0.9615(9) 0.1733(6) 0.8175(6) 0.137(3) Uani 0.65 1 d PD A 1
C33A C 1.0014(15) 0.2656(8) 0.7943(9) 0.132(2) Uani 0.65 1 d PD A 1
H33A H 0.9422 0.3175 0.7944 0.158 Uiso 0.65 1 calc PR A 1
H33B H 1.0877 0.3062 0.8519 0.158 Uiso 0.65 1 calc PR A 1
C34A C 0.9995(14) 0.2161(8) 0.6841(9) 0.132(2) Uani 0.65 1 d PD A 1
H34A H 1.0862 0.2323 0.6909 0.158 Uiso 0.65 1 calc PR A 1
H34B H 0.9441 0.2497 0.6342 0.158 Uiso 0.65 1 calc PR A 1
C35A C 0.9540(14) 0.0969(8) 0.6325(10) 0.132(2) Uani 0.65 1 d PD A 1
H35A H 1.0246 0.0571 0.635 0.158 Uiso 0.65 1 calc PR A 1
H35B H 0.89 0.0728 0.5531 0.158 Uiso 0.65 1 calc PR A 1
C36A C 0.8971(15) 0.0796(11) 0.7049(8) 0.132(2) Uani 0.65 1 d PD A 1
H36A H 0.9101 0.0086 0.7129 0.158 Uiso 0.65 1 calc PR A 1
H36B H 0.8049 0.0782 0.671 0.158 Uiso 0.65 1 calc PR A 1
O2B O 0.9626(17) 0.0956(11) 0.7793(12) 0.137(3) Uani 0.35 1 d PD B 2
C33B C 1.010(3) 0.2123(13) 0.7974(17) 0.132(2) Uani 0.35 1 d PD B 2
H33C H 1.002 0.2642 0.8643 0.158 Uiso 0.35 1 calc PR B 2
H33D H 1.1007 0.2214 0.8142 0.158 Uiso 0.35 1 calc PR B 2
C34B C 0.940(2) 0.2425(15) 0.6993(16) 0.132(2) Uani 0.35 1 d PD B 2
H34C H 0.8809 0.2911 0.7123 0.158 Uiso 0.35 1 calc PR B 2
H34D H 0.9989 0.2773 0.6791 0.158 Uiso 0.35 1 calc PR B 2
C35B C 0.874(3) 0.1306(14) 0.6146(17) 0.132(2) Uani 0.35 1 d PD B 2
H35C H 0.9261 0.098 0.5752 0.158 Uiso 0.35 1 calc PR B 2
H35D H 0.7924 0.1344 0.5576 0.158 Uiso 0.35 1 calc PR B 2
C36B C 0.850(2) 0.060(2) 0.6701(16) 0.132(2) Uani 0.35 1 d PD B 2
H36C H 0.7726 0.0713 0.6813 0.158 Uiso 0.35 1 calc PR B 2
H36D H 0.8405 -0.0187 0.624 0.158 Uiso 0.35 1 calc PR B 2
O1 O 1.1618(2) -0.01722(19) 0.0227(2) 0.0542(6) Uani 1 1 d . . .
F1 F 1.2453(2) 0.2067(2) 0.5644(3) 0.1028(10) Uani 1 1 d . . .
F2 F 1.4062(3) 0.4529(2) 0.6692(3) 0.0945(8) Uani 1 1 d . . .
F3 F 1.3552(3) 0.3401(3) 0.7446(2) 0.1055(11) Uani 1 1 d . . .
F4 F 1.1958(2) 0.3771(2) 0.6082(2) 0.0826(8) Uani 1 1 d . . .
F5 F 1.2962(2) 0.3242(2) 0.49354(18) 0.0752(7) Uani 1 1 d . . .
F6 F 1.45270(19) 0.28184(19) 0.62896(19) 0.0637(6) Uani 1 1 d . . .
P1 P 0.98454(6) 0.31694(6) 0.18123(6) 0.03035(19) Uani 1 1 d . . .
P2 P 1.24755(7) 0.08625(6) 0.12055(7) 0.0376(2) Uani 1 1 d . . .
P3 P 1.32378(8) 0.32942(8) 0.61879(7) 0.0481(2) Uani 1 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'
H H 0 0 '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'
F F 0.0171 0.0103 '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'
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
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 118.8(3) . . ?
C6 C1 P2 124.8(2) . . ?
C2 C1 P2 116.4(3) . . ?
C3 C2 C1 120.1(3) . . ?
C2 C3 C4 121.0(3) . . ?
C3 C4 C5 119.5(3) . . ?
C6 C5 C4 120.3(3) . . ?
C5 C6 C1 120.3(3) . . ?
C8 C7 C12 119.1(3) . . ?
C8 C7 P2 124.7(2) . . ?
C12 C7 P2 116.2(3) . . ?
C7 C8 C9 120.2(3) . . ?
C10 C9 C8 119.6(3) . . ?
C11 C10 C9 120.9(3) . . ?
C10 C11 C12 119.8(3) . . ?
C11 C12 C7 120.3(4) . . ?
C14 C13 P2 111.89(19) . . ?
C13 C14 P1 112.03(18) . . ?
C20 C15 C16 119.3(3) . . ?
C20 C15 P1 120.0(2) . . ?
C16 C15 P1 120.8(2) . . ?
C17 C16 C15 120.3(3) . . ?
C18 C17 C16 120.2(3) . . ?
C17 C18 C19 120.1(3) . . ?
C18 C19 C20 120.2(3) . . ?
C15 C20 C19 119.9(3) . . ?
C26 C21 C22 120.0(3) . . ?
C26 C21 P1 120.4(2) . . ?
C22 C21 P1 119.5(2) . . ?
C23 C22 C21 120.0(3) . . ?
C22 C23 C24 119.7(3) . . ?
C25 C24 C23 120.5(3) . . ?
C24 C25 C26 120.6(3) . . ?
C21 C26 C25 119.2(3) . . ?
C28 C27 C32 119.3(3) . . ?
C28 C27 P1 121.5(2) . . ?
C32 C27 P1 119.0(2) . . ?
C29 C28 C27 119.7(3) . . ?
C30 C29 C28 121.3(4) . . ?
C29 C30 C31 119.3(3) . . ?
C32 C31 C30 120.3(3) . . ?
C31 C32 C27 119.8(3) . . ?
C33A O2A C36A 105.2(7) . . ?
C34A C33A O2A 105.5(7) . . ?
C33A C34A C35A 112.6(8) . . ?
C34A C35A C36A 102.2(9) . . ?
C35A C36A O2A 107.0(8) . . ?
C36B O2B C33B 101.3(15) . . ?
C34B C33B O2B 114.2(16) . . ?
C35B C34B C33B 97.9(17) . . ?
C34B C35B C36B 110.1(17) . . ?
O2B C36B C35B 105.0(16) . . ?
C27 P1 C21 109.96(14) . . ?
C27 P1 C15 109.58(14) . . ?
C21 P1 C15 109.18(13) . . ?
C27 P1 C14 109.91(13) . . ?
C21 P1 C14 109.26(13) . . ?
C15 P1 C14 108.94(13) . . ?
O1 P2 C1 112.22(15) . . ?
O1 P2 C7 111.24(15) . . ?
C1 P2 C7 107.42(14) . . ?
O1 P2 C13 113.85(14) . . ?
C1 P2 C13 105.50(13) . . ?
C7 P2 C13 106.15(13) . . ?
F1 P3 F3 92.5(2) . . ?
F1 P3 F4 90.23(16) . . ?
F3 P3 F4 90.80(14) . . ?
F1 P3 F2 177.06(17) . . ?
F3 P3 F2 89.91(19) . . ?
F4 P3 F2 91.39(16) . . ?
F1 P3 F5 90.15(18) . . ?
F3 P3 F5 177.31(19) . . ?
F4 P3 F5 89.45(12) . . ?
F2 P3 F5 87.40(16) . . ?
F1 P3 F6 89.97(13) . . ?
F3 P3 F6 89.48(14) . . ?
F4 P3 F6 179.66(14) . . ?
F2 P3 F6 88.41(14) . . ?
F5 P3 F6 90.27(12) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.394(5) . ?
C1 C2 1.406(4) . ?
C1 P2 1.794(3) . ?
C2 C3 1.373(5) . ?
C3 C4 1.376(6) . ?
C4 C5 1.391(5) . ?
C5 C6 1.383(5) . ?
C7 C8 1.377(5) . ?
C7 C12 1.403(4) . ?
C7 P2 1.798(3) . ?
C8 C9 1.388(5) . ?
C9 C10 1.382(5) . ?
C10 C11 1.361(6) . ?
C11 C12 1.379(5) . ?
C13 C14 1.521(4) . ?
C13 P2 1.815(3) . ?
C14 P1 1.808(3) . ?
C15 C20 1.385(4) . ?
C15 C16 1.389(4) . ?
C15 P1 1.795(3) . ?
C16 C17 1.378(4) . ?
C17 C18 1.371(5) . ?
C18 C19 1.377(5) . ?
C19 C20 1.386(5) . ?
C21 C26 1.386(4) . ?
C21 C22 1.389(4) . ?
C21 P1 1.794(3) . ?
C22 C23 1.381(4) . ?
C23 C24 1.387(5) . ?
C24 C25 1.361(5) . ?
C25 C26 1.392(5) . ?
C27 C28 1.383(4) . ?
C27 C32 1.396(4) . ?
C27 P1 1.787(3) . ?
C28 C29 1.380(5) . ?
C29 C30 1.357(6) . ?
C30 C31 1.392(6) . ?
C31 C32 1.373(5) . ?
O2A C33A 1.439(8) . ?
O2A C36A 1.464(8) . ?
C33A C34A 1.413(8) . ?
C34A C35A 1.429(8) . ?
C35A C36A 1.455(9) . ?
O2B C36B 1.441(10) . ?
O2B C33B 1.484(10) . ?
C33B C34B 1.460(18) . ?
C34B C35B 1.445(10) . ?
C35B C36B 1.450(10) . ?
O1 P2 1.478(2) . ?
F1 P3 1.561(3) . ?
F2 P3 1.593(3) . ?
F3 P3 1.570(2) . ?
F4 P3 1.585(2) . ?
F5 P3 1.594(2) . ?
F6 P3 1.595(2) . ?
