#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/30/77/4307754.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_4307754
loop_
_publ_author_name
'C. Adam Dyker'
'Neil Burford'
'Gabriel Menard'
'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
;
Monocyclic Di- and Triphosphinophosphonium Cations: New Foundational
Frameworks for catena-Phosphorus Chemistry
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              4277
_journal_page_last               4285
_journal_paper_doi               10.1021/ic0622499
_journal_volume                  46
_journal_year                    2007
_chemical_formula_sum            'C17 H37 F3 O3 P4 S'
_chemical_formula_weight         502.41
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.354(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.773(10)
_cell_length_b                   12.781(9)
_cell_length_c                   15.071(10)
_cell_measurement_reflns_used    7324
_cell_measurement_temperature    208(1)
_cell_measurement_theta_max      28.34
_cell_measurement_theta_min      2.46
_cell_volume                     2625(3)
_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      208(1)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_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  0.0447
_diffrn_reflns_av_sigmaI/netI    0.0554
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17562
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         1.87
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Bruker AXS SMART1000/P4'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.403
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997b)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Irregular
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.425
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.125
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         5889
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0760
_refine_ls_R_factor_gt           0.0406
_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)+(0.0476P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0962
_reflns_number_gt                4041
_reflns_number_total             5889
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ic0622499-file004.cif
_cod_data_source_block           nb050871
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4307754
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.92525(4) 0.70894(4) 0.16103(4) 0.02528(14) Uani 1 1 d . . .
P2 P 1.04442(4) 0.81331(4) 0.21806(4) 0.02901(14) Uani 1 1 d . . .
P3 P 1.06970(4) 0.83609(4) 0.07605(4) 0.02874(15) Uani 1 1 d . . .
P4 P 0.98728(4) 0.68788(4) 0.03714(4) 0.02801(14) Uani 1 1 d . . .
C1 C 0.91483(17) 0.58583(15) 0.22352(15) 0.0305(5) Uani 1 1 d . . .
C2 C 1.0187(2) 0.5433(2) 0.2550(2) 0.0398(6) Uani 1 1 d . . .
C3 C 0.8625(2) 0.6115(2) 0.30311(19) 0.0402(6) Uani 1 1 d . . .
C4 C 0.8555(2) 0.50802(18) 0.16004(19) 0.0379(6) Uani 1 1 d . . .
C5 C 0.98369(17) 0.93797(16) 0.24952(16) 0.0326(5) Uani 1 1 d . . .
C6 C 1.0707(2) 1.0122(2) 0.2786(2) 0.0492(7) Uani 1 1 d . . .
C7 C 0.9308(3) 0.9116(2) 0.3287(2) 0.0559(9) Uani 1 1 d . . .
C8 C 0.9134(2) 0.98982(19) 0.17591(19) 0.0377(6) Uani 1 1 d . . .
C9 C 1.20171(16) 0.79428(18) 0.07839(17) 0.0365(5) Uani 1 1 d . . .
C10 C 1.2162(2) 0.7851(3) -0.0195(2) 0.0603(9) Uani 1 1 d . . .
C11 C 1.2645(2) 0.8823(3) 0.1257(3) 0.0567(8) Uani 1 1 d . . .
C12 C 1.2299(2) 0.6912(2) 0.1266(2) 0.0508(7) Uani 1 1 d . . .
C13 C 0.88785(16) 0.72688(16) -0.05611(15) 0.0306(5) Uani 1 1 d . . .
C14 C 0.8378(2) 0.8323(2) -0.04422(18) 0.0383(6) Uani 1 1 d . . .
C15 C 0.8113(2) 0.6388(2) -0.0670(2) 0.0459(7) Uani 1 1 d . . .
C16 C 0.9410(2) 0.7320(2) -0.13870(18) 0.0413(6) Uani 1 1 d . . .
S S 0.62221(4) 0.76492(4) 0.13960(4) 0.03436(15) Uani 1 1 d . . .
O1 O 0.69811(13) 0.84347(14) 0.15060(13) 0.0521(5) Uani 1 1 d . . .
O2 O 0.55516(15) 0.76978(17) 0.20298(14) 0.0669(6) Uani 1 1 d . . .
O3 O 0.65781(16) 0.66307(14) 0.12017(16) 0.0666(6) Uani 1 1 d . . .
C17 C 0.5465(2) 0.8027(3) 0.0365(2) 0.0568(8) Uani 1 1 d . . .
F1 F 0.50977(16) 0.89823(16) 0.04255(15) 0.0968(7) Uani 1 1 d . . .
F2 F 0.59461(14) 0.7977(2) -0.03292(12) 0.0976(7) Uani 1 1 d . . .
F3 F 0.47040(13) 0.73759(19) 0.01851(14) 0.0966(7) Uani 1 1 d . . .
H1 H 0.8365(16) 0.7511(16) 0.1512(15) 0.040(6) Uiso 1 1 d . . .
H2A H 1.0538(17) 0.5356(17) 0.2038(17) 0.038(7) Uiso 1 1 d . . .
H2B H 1.0563(18) 0.5904(19) 0.2948(17) 0.043(7) Uiso 1 1 d . . .
H2C H 1.0130(19) 0.473(2) 0.2840(18) 0.053(7) Uiso 1 1 d . . .
H3A H 0.8997(18) 0.6612(19) 0.3410(17) 0.040(7) Uiso 1 1 d . . .
H3B H 0.8549(19) 0.548(2) 0.3383(17) 0.052(8) Uiso 1 1 d . . .
H3C H 0.7995(19) 0.6332(19) 0.2849(16) 0.039(7) Uiso 1 1 d . . .
H4A H 0.848(2) 0.445(2) 0.1918(18) 0.059(8) Uiso 1 1 d . . .
H4B H 0.7927(19) 0.5282(18) 0.1382(16) 0.037(7) Uiso 1 1 d . . .
H4C H 0.8895(17) 0.4951(18) 0.1103(17) 0.039(7) Uiso 1 1 d . . .
H6A H 1.110(2) 1.024(2) 0.226(2) 0.063(9) Uiso 1 1 d . . .
H6B H 1.1098(19) 0.986(2) 0.3281(19) 0.045(8) Uiso 1 1 d . . .
H6C H 1.040(2) 1.079(2) 0.2957(17) 0.055(8) Uiso 1 1 d . . .
H7A H 0.981(2) 0.884(3) 0.375(2) 0.080(11) Uiso 1 1 d . . .
H7B H 0.904(2) 0.976(2) 0.3521(18) 0.060(8) Uiso 1 1 d . . .
H7C H 0.873(2) 0.863(3) 0.312(2) 0.078(11) Uiso 1 1 d . . .
H8A H 0.9438(18) 1.0072(19) 0.1235(18) 0.044(7) Uiso 1 1 d . . .
H8B H 0.8900(18) 1.057(2) 0.1989(17) 0.048(7) Uiso 1 1 d . . .
H8C H 0.858(2) 0.951(2) 0.1545(18) 0.056(8) Uiso 1 1 d . . .
H10A H 1.170(2) 0.733(3) -0.051(2) 0.077(11) Uiso 1 1 d . . .
H10B H 1.283(2) 0.769(2) -0.020(2) 0.071(9) Uiso 1 1 d . . .
H10C H 1.199(2) 0.845(3) -0.050(2) 0.070(11) Uiso 1 1 d . . .
H11A H 1.335(2) 0.864(2) 0.1265(17) 0.057(8) Uiso 1 1 d . . .
H11B H 1.251(3) 0.942(3) 0.093(2) 0.089(12) Uiso 1 1 d . . .
H11C H 1.248(2) 0.890(3) 0.189(2) 0.090(12) Uiso 1 1 d . . .
H12A H 1.2249(19) 0.700(2) 0.192(2) 0.055(8) Uiso 1 1 d . . .
H12B H 1.193(2) 0.633(2) 0.0987(19) 0.060(9) Uiso 1 1 d . . .
H12C H 1.2974(19) 0.6763(18) 0.1257(16) 0.040(7) Uiso 1 1 d . . .
H14A H 0.885(2) 0.891(2) -0.0381(18) 0.054(8) Uiso 1 1 d . . .
H14B H 0.8034(17) 0.8320(17) 0.0065(16) 0.036(6) Uiso 1 1 d . . .
H14C H 0.7849(18) 0.8465(18) -0.0979(17) 0.041(7) Uiso 1 1 d . . .
H15A H 0.7748(19) 0.6358(19) -0.0154(18) 0.050(8) Uiso 1 1 d . . .
H15B H 0.8381(19) 0.573(2) -0.0780(17) 0.046(7) Uiso 1 1 d . . .
H15C H 0.7581(18) 0.6532(18) -0.1187(17) 0.042(7) Uiso 1 1 d . . .
H16A H 0.9706(19) 0.667(2) -0.1482(17) 0.049(8) Uiso 1 1 d . . .
H16B H 0.8942(18) 0.7484(19) -0.1927(18) 0.044(7) Uiso 1 1 d . . .
H16C H 0.9886(19) 0.785(2) -0.1322(17) 0.046(7) Uiso 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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 P1 P4 113.58(8) . . ?
C1 P1 P2 115.29(9) . . ?
P4 P1 P2 92.68(5) . . ?
C1 P1 H1 105.3(9) . . ?
P4 P1 H1 115.1(10) . . ?
P2 P1 H1 115.0(9) . . ?
C5 P2 P1 106.12(9) . . ?
C5 P2 P3 105.43(8) . . ?
P1 P2 P3 85.17(4) . . ?
C9 P3 P2 103.20(8) . . ?
C9 P3 P4 102.42(9) . . ?
P2 P3 P4 89.83(4) . . ?
C13 P4 P1 105.89(9) . . ?
C13 P4 P3 104.92(8) . . ?
P1 P4 P3 85.30(4) . . ?
C3 C1 C4 111.2(2) . . ?
C3 C1 C2 111.0(2) . . ?
C4 C1 C2 110.6(2) . . ?
C3 C1 P1 107.39(15) . . ?
C4 C1 P1 107.95(17) . . ?
C2 C1 P1 108.67(15) . . ?
C1 C2 H2A 109.7(14) . . ?
C1 C2 H2B 111.6(15) . . ?
H2A C2 H2B 106.0(19) . . ?
C1 C2 H2C 108.8(15) . . ?
H2A C2 H2C 109.4(19) . . ?
H2B C2 H2C 111(2) . . ?
C1 C3 H3A 110.0(14) . . ?
C1 C3 H3B 110.2(14) . . ?
H3A C3 H3B 109(2) . . ?
C1 C3 H3C 111.5(15) . . ?
H3A C3 H3C 112(2) . . ?
H3B C3 H3C 104(2) . . ?
C1 C4 H4A 109.0(17) . . ?
C1 C4 H4B 115.6(15) . . ?
H4A C4 H4B 105(2) . . ?
C1 C4 H4C 108.9(14) . . ?
H4A C4 H4C 110(2) . . ?
H4B C4 H4C 108(2) . . ?
C8 C5 C7 110.1(2) . . ?
C8 C5 C6 109.0(2) . . ?
C7 C5 C6 110.8(3) . . ?
C8 C5 P2 116.35(17) . . ?
C7 C5 P2 106.81(16) . . ?
C6 C5 P2 103.65(17) . . ?
C5 C6 H6A 110.2(17) . . ?
C5 C6 H6B 110.1(16) . . ?
H6A C6 H6B 112(2) . . ?
C5 C6 H6C 104.9(16) . . ?
H6A C6 H6C 111(2) . . ?
H6B C6 H6C 109(2) . . ?
C5 C7 H7A 105.5(19) . . ?
C5 C7 H7B 110.2(15) . . ?
H7A C7 H7B 108(2) . . ?
C5 C7 H7C 112.5(18) . . ?
H7A C7 H7C 114(3) . . ?
H7B C7 H7C 106(2) . . ?
C5 C8 H8A 113.0(15) . . ?
C5 C8 H8B 109.1(15) . . ?
H8A C8 H8B 106.5(19) . . ?
C5 C8 H8C 115.3(17) . . ?
H8A C8 H8C 106(2) . . ?
H8B C8 H8C 107(2) . . ?
C10 C9 C12 109.6(3) . . ?
C10 C9 C11 111.4(3) . . ?
C12 C9 C11 109.0(3) . . ?
C10 C9 P3 105.34(19) . . ?
C12 C9 P3 115.45(17) . . ?
C11 C9 P3 106.11(18) . . ?
C9 C10 H10A 111.1(18) . . ?
C9 C10 H10B 106.8(19) . . ?
H10A C10 H10B 113(2) . . ?
C9 C10 H10C 111.4(19) . . ?
H10A C10 H10C 103(3) . . ?
H10B C10 H10C 111(3) . . ?
C9 C11 H11A 108.6(16) . . ?
C9 C11 H11B 108(2) . . ?
H11A C11 H11B 109(3) . . ?
C9 C11 H11C 108.7(19) . . ?
H11A C11 H11C 111(3) . . ?
H11B C11 H11C 111(3) . . ?
C9 C12 H12A 109.1(16) . . ?
C9 C12 H12B 112.1(17) . . ?
H12A C12 H12B 114(2) . . ?
C9 C12 H12C 110.3(14) . . ?
H12A C12 H12C 104(2) . . ?
H12B C12 H12C 107(2) . . ?
C16 C13 C14 109.4(2) . . ?
C16 C13 C15 110.3(2) . . ?
C14 C13 C15 110.1(2) . . ?
C16 C13 P4 103.67(17) . . ?
C14 C13 P4 115.82(17) . . ?
C15 C13 P4 107.42(17) . . ?
C13 C14 H14A 112.1(15) . . ?
C13 C14 H14B 111.9(13) . . ?
H14A C14 H14B 109(2) . . ?
C13 C14 H14C 110.1(14) . . ?
H14A C14 H14C 109(2) . . ?
H14B C14 H14C 104.7(19) . . ?
C13 C15 H15A 111.4(15) . . ?
C13 C15 H15B 113.1(16) . . ?
H15A C15 H15B 111(2) . . ?
C13 C15 H15C 111.1(14) . . ?
H15A C15 H15C 103(2) . . ?
H15B C15 H15C 107(2) . . ?
C13 C16 H16A 110.6(16) . . ?
C13 C16 H16B 110.4(14) . . ?
H16A C16 H16B 108(2) . . ?
C13 C16 H16C 110.7(15) . . ?
H16A C16 H16C 110(2) . . ?
H16B C16 H16C 107(2) . . ?
O2 S O3 116.77(13) . . ?
O2 S O1 115.01(12) . . ?
O3 S O1 113.05(13) . . ?
O2 S C17 102.45(14) . . ?
O3 S C17 103.79(14) . . ?
O1 S C17 103.38(14) . . ?
F2 C17 F1 109.8(3) . . ?
F2 C17 F3 106.2(3) . . ?
F1 C17 F3 106.9(2) . . ?
F2 C17 S 112.0(2) . . ?
F1 C17 S 111.3(2) . . ?
F3 C17 S 110.3(2) . . ?
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
P1 C1 1.850(2) . ?
P1 P4 2.1800(14) . ?
P1 P2 2.1914(13) . ?
P1 H1 1.32(2) . ?
P2 C5 1.892(2) . ?
P2 P3 2.2368(17) . ?
P3 C9 1.890(3) . ?
P3 P4 2.2423(14) . ?
P4 C13 1.881(3) . ?
C1 C3 1.522(3) . ?
C1 C4 1.532(3) . ?
C1 C2 1.539(3) . ?
C2 H2A 0.97(2) . ?
C2 H2B 0.95(3) . ?
C2 H2C 1.01(3) . ?
C3 H3A 0.95(3) . ?
C3 H3B 0.98(3) . ?
C3 H3C 0.91(3) . ?
C4 H4A 0.96(3) . ?
C4 H4B 0.92(3) . ?
C4 H4C 0.96(2) . ?
C5 C8 1.515(4) . ?
C5 C7 1.523(4) . ?
C5 C6 1.542(4) . ?
C6 H6A 1.03(3) . ?
C6 H6B 0.92(3) . ?
C6 H6C 1.00(3) . ?
C7 H7A 0.97(3) . ?
C7 H7B 0.99(3) . ?
C7 H7C 1.01(3) . ?
C8 H8A 0.97(3) . ?
C8 H8B 1.00(3) . ?
C8 H8C 0.93(3) . ?
C9 C10 1.522(4) . ?
C9 C12 1.528(4) . ?
C9 C11 1.530(4) . ?
C10 H10A 0.99(3) . ?
C10 H10B 0.95(3) . ?
C10 H10C 0.91(3) . ?
C11 H11A 1.00(3) . ?
C11 H11B 0.91(4) . ?
C11 H11C 1.02(3) . ?
C12 H12A 1.00(3) . ?
C12 H12B 0.97(3) . ?
C12 H12C 0.95(2) . ?
C13 C16 1.534(3) . ?
C13 C14 1.535(3) . ?
C13 C15 1.535(3) . ?
C14 H14A 0.99(3) . ?
C14 H14B 0.96(2) . ?
C14 H14C 1.02(3) . ?
C15 H15A 0.98(3) . ?
C15 H15B 0.95(3) . ?
C15 H15C 1.01(3) . ?
C16 H16A 0.95(3) . ?
C16 H16B 0.98(3) . ?
C16 H16C 0.94(3) . ?
S O2 1.4233(19) . ?
S O3 1.4362(19) . ?
S O1 1.4415(19) . ?
S C17 1.807(3) . ?
C17 F2 1.319(3) . ?
C17 F1 1.330(3) . ?
C17 F3 1.334(4) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21155799
