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#$Date: 2016-03-21 19:00:37 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178832 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/86/4108687.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_4108687
loop_
_publ_author_name
'Yuen-ying Carpenter'
'C. Adam Dyker'
'Neil Burford'
'Michael D. Lumsden'
'Andreas Decken'
_publ_contact_author_address
;Department of Chemistry
University of New Brunswick
Fredericton, NB
E3B 6E2
Canada
;
_publ_contact_author_email       adecken@unb.ca
_publ_contact_author_fax         '(506) 453-4981'
_publ_contact_author_name        'Andreas Decken'
_publ_contact_author_phone       '(506) 453-4875'
_publ_section_title
;
 2,3-Diphosphino-1,4-diphosphonium Ions
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15732
_journal_page_last               15741
_journal_paper_doi               10.1021/ja805911a
_journal_volume                  130
_journal_year                    2008
_chemical_formula_moiety         'C40 H40 P4, 2(C F3 O3 S)'
_chemical_formula_sum            'C42 H40 F6 O6 P4 S2'
_chemical_formula_weight         942.74
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 102.483(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.5968(16)
_cell_length_b                   14.5043(16)
_cell_length_c                   19.895(2)
_cell_measurement_reflns_used    6320
_cell_measurement_temperature    173(1)
_cell_measurement_theta_max      27.64
_cell_measurement_theta_min      2.34
_cell_volume                     4394.3(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(1)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0261
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            15089
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.94
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              K760
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.338
_exptl_absorpt_correction_T_max  0.9354
_exptl_absorpt_correction_T_min  0.8491
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997b)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.425
_exptl_crystal_description       Rod
_exptl_crystal_F_000             1944
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.820
_refine_diff_density_min         -0.579
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4932
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0461
_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)+(0.0496P)²+10.4824P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1108
_refine_ls_wR_factor_ref         0.1282
_reflns_number_gt                3960
_reflns_number_total             4932
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja805911a_si_001_70746.cif
_cod_data_source_block           nb070746
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4108687
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
P1 P 0.04123(4) 0.91148(4) 0.13710(3) 0.02424(14) Uani 1 1 d .
P2 P 0.06920(4) 0.86268(4) 0.24459(3) 0.02589(15) Uani 1 1 d .
C1 C -0.03658(14) 0.84575(16) 0.07600(11) 0.0274(5) Uani 1 1 d .
C2 C -0.11282(15) 0.88451(18) 0.03668(13) 0.0340(5) Uani 1 1 d .
H2 H -0.1268 0.9472 0.0430 0.041 Uiso 1 1 calc R
C3 C -0.16818(18) 0.8306(2) -0.01191(14) 0.0450(6) Uani 1 1 d .
H3 H -0.2204 0.8565 -0.0388 0.054 Uiso 1 1 calc R
C4 C -0.14771(19) 0.7398(2) -0.02129(14) 0.0474(7) Uani 1 1 d .
H4 H -0.1859 0.7035 -0.0548 0.057 Uiso 1 1 calc R
C5 C -0.07236(19) 0.70092(19) 0.01748(14) 0.0443(6) Uani 1 1 d .
H5 H -0.0591 0.6381 0.0109 0.053 Uiso 1 1 calc R
C6 C -0.01584(17) 0.75362(17) 0.06613(12) 0.0343(5) Uani 1 1 d .
H6 H 0.0365 0.7273 0.0925 0.041 Uiso 1 1 calc R
C7 C 0.14451(14) 0.90677(16) 0.11054(12) 0.0287(5) Uani 1 1 d .
C8 C 0.22176(16) 0.93135(19) 0.15705(13) 0.0390(6) Uani 1 1 d .
H8 H 0.2206 0.9472 0.2032 0.047 Uiso 1 1 calc R
C9 C 0.30049(17) 0.9324(2) 0.13484(15) 0.0480(7) Uani 1 1 d .
H9 H 0.3533 0.9497 0.1659 0.058 Uiso 1 1 calc R
C10 C 0.30252(18) 0.9082(2) 0.06773(16) 0.0487(7) Uani 1 1 d .
H10 H 0.3566 0.9090 0.0531 0.058 Uiso 1 1 calc R
C11 C 0.22620(17) 0.8831(2) 0.02223(14) 0.0425(6) Uani 1 1 d .
H11 H 0.2281 0.8659 -0.0235 0.051 Uiso 1 1 calc R
C12 C 0.14700(16) 0.88276(18) 0.04285(12) 0.0337(5) Uani 1 1 d .
H12 H 0.0945 0.8663 0.0112 0.040 Uiso 1 1 calc R
C13 C 0.00699(15) 1.02958(15) 0.14207(11) 0.0274(5) Uani 1 1 d .
C14 C -0.07671(15) 1.05170(16) 0.15199(12) 0.0305(5) Uani 1 1 d .
H14 H -0.1184 1.0043 0.1530 0.037 Uiso 1 1 calc R
C15 C -0.09857(17) 1.14297(17) 0.16027(14) 0.0375(6) Uani 1 1 d .
H15 H -0.1555 1.1581 0.1668 0.045 Uiso 1 1 calc R
C16 C -0.0379(2) 1.21211(18) 0.15907(15) 0.0457(7) Uani 1 1 d .
H16 H -0.0532 1.2745 0.1649 0.055 Uiso 1 1 calc R
C17 C 0.0448(2) 1.19075(18) 0.14949(17) 0.0485(7) Uani 1 1 d .
H17 H 0.0861 1.2386 0.1485 0.058 Uiso 1 1 calc R
C18 C 0.06790(18) 1.09978(17) 0.14133(15) 0.0389(6) Uani 1 1 d .
H18 H 0.1251 1.0853 0.1353 0.047 Uiso 1 1 calc R
C19 C 0.10678(18) 0.74239(17) 0.23884(13) 0.0368(5) Uani 1 1 d .
H19A H 0.0554 0.7013 0.2242 0.044 Uiso 1 1 calc R
H19B H 0.1435 0.7383 0.2041 0.044 Uiso 1 1 calc R
C20 C 0.1598(2) 0.7118(2) 0.30872(16) 0.0622(9) Uani 1 1 d .
H20A H 0.2083 0.7550 0.3244 0.093 Uiso 1 1 calc R
H20B H 0.1835 0.6499 0.3047 0.093 Uiso 1 1 calc R
H20C H 0.1218 0.7107 0.3420 0.093 Uiso 1 1 calc R
C21 C 0.0712(2) 0.4785(2) 0.1509(2) 0.0599(9) Uani 1 1 d .
F1 F 0.0873(2) 0.40778(18) 0.19550(19) 0.1264(12) Uani 1 1 d .
F2 F 0.02207(15) 0.4431(2) 0.09684(16) 0.1235(13) Uani 1 1 d .
F3 F 0.02386(15) 0.53906(16) 0.17641(15) 0.0944(9) Uani 1 1 d .
S1 S 0.17271(4) 0.52748(5) 0.13627(4) 0.03997(17) Uani 1 1 d .
O1 O 0.14436(17) 0.6050(2) 0.09339(14) 0.0763(8) Uani 1 1 d .
O2 O 0.21217(16) 0.45483(18) 0.10593(17) 0.0841(9) Uani 1 1 d .
O3 O 0.21736(16) 0.55398(17) 0.20412(12) 0.0647(6) 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 0.0000 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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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_3
C1 P1 C7 107.33(10) .
C1 P1 C13 112.13(11) .
C7 P1 C13 110.26(11) .
C1 P1 P2 116.71(8) .
C7 P1 P2 105.68(8) .
C13 P1 P2 104.51(8) .
C19 P2 P1 103.97(8) .
C19 P2 P2 109.52(9) 2
P1 P2 P2 95.84(4) 2
C2 C1 C6 120.1(2) .
C2 C1 P1 122.42(18) .
C6 C1 P1 117.35(18) .
C3 C2 C1 119.3(2) .
C3 C2 H2 120.3 .
C1 C2 H2 120.3 .
C4 C3 C2 120.3(3) .
C4 C3 H3 119.8 .
C2 C3 H3 119.8 .
C3 C4 C5 120.6(2) .
C3 C4 H4 119.7 .
C5 C4 H4 119.7 .
C4 C5 C6 120.1(3) .
C4 C5 H5 120.0 .
C6 C5 H5 120.0 .
C5 C6 C1 119.5(2) .
C5 C6 H6 120.3 .
C1 C6 H6 120.3 .
C8 C7 C12 120.1(2) .
C8 C7 P1 119.59(18) .
C12 C7 P1 120.26(18) .
C9 C8 C7 119.1(2) .
C9 C8 H8 120.5 .
C7 C8 H8 120.5 .
C10 C9 C8 120.5(3) .
C10 C9 H9 119.7 .
C8 C9 H9 119.7 .
C11 C10 C9 120.1(2) .
C11 C10 H10 119.9 .
C9 C10 H10 119.9 .
C10 C11 C12 120.4(2) .
C10 C11 H11 119.8 .
C12 C11 H11 119.8 .
C11 C12 C7 119.8(2) .
C11 C12 H12 120.1 .
C7 C12 H12 120.1 .
C18 C13 C14 119.5(2) .
C18 C13 P1 118.84(18) .
C14 C13 P1 121.47(17) .
C15 C14 C13 119.8(2) .
C15 C14 H14 120.1 .
C13 C14 H14 120.1 .
C16 C15 C14 120.2(2) .
C16 C15 H15 119.9 .
C14 C15 H15 119.9 .
C17 C16 C15 120.2(2) .
C17 C16 H16 119.9 .
C15 C16 H16 119.9 .
C16 C17 C18 120.3(2) .
C16 C17 H17 119.9 .
C18 C17 H17 119.9 .
C17 C18 C13 119.9(2) .
C17 C18 H18 120.0 .
C13 C18 H18 120.0 .
C20 C19 P2 109.60(19) .
C20 C19 H19A 109.8 .
P2 C19 H19A 109.8 .
C20 C19 H19B 109.8 .
P2 C19 H19B 109.8 .
H19A C19 H19B 108.2 .
C19 C20 H20A 109.5 .
C19 C20 H20B 109.5 .
H20A C20 H20B 109.5 .
C19 C20 H20C 109.5 .
H20A C20 H20C 109.5 .
H20B C20 H20C 109.5 .
F2 C21 F3 107.9(3) .
F2 C21 F1 103.9(3) .
F3 C21 F1 107.1(3) .
F2 C21 S1 113.9(3) .
F3 C21 S1 112.4(2) .
F1 C21 S1 111.1(3) .
O2 S1 O1 116.05(18) .
O2 S1 O3 115.67(17) .
O1 S1 O3 112.20(17) .
O2 S1 C21 104.52(15) .
O1 S1 C21 103.68(17) .
O3 S1 C21 102.57(16) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 C1 1.795(2) .
P1 C7 1.802(2) .
P1 C13 1.803(2) .
P1 P2 2.2048(8) .
P2 C19 1.852(2) .
P2 P2 2.2153(11) 2
C1 C2 1.393(3) .
C1 C6 1.399(3) .
C2 C3 1.390(4) .
C2 H2 0.9500 .
C3 C4 1.378(4) .
C3 H3 0.9500 .
C4 C5 1.379(4) .
C4 H4 0.9500 .
C5 C6 1.389(4) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C7 C8 1.397(3) .
C7 C12 1.400(3) .
C8 C9 1.392(4) .
C8 H8 0.9500 .
C9 C10 1.387(4) .
C9 H9 0.9500 .
C10 C11 1.380(4) .
C10 H10 0.9500 .
C11 C12 1.383(3) .
C11 H11 0.9500 .
C12 H12 0.9500 .
C13 C18 1.395(3) .
C13 C14 1.399(3) .
C14 C15 1.386(3) .
C14 H14 0.9500 .
C15 C16 1.383(4) .
C15 H15 0.9500 .
C16 C17 1.379(4) .
C16 H16 0.9500 .
C17 C18 1.387(4) .
C17 H17 0.9500 .
C18 H18 0.9500 .
C19 C20 1.522(4) .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
C21 F2 1.284(4) .
C21 F3 1.318(4) .
C21 F1 1.344(5) .
C21 S1 1.815(3) .
S1 O2 1.419(2) .
S1 O1 1.423(2) .
S1 O3 1.431(2) .
