#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/7/01/97/7019702.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_7019702
loop_
_publ_author_name
'Palomas, David'
'Holle, Sigrid'
'Inés, Blanca'
'Bruns, Hans'
'Goddard, Richard'
'Alcarazo, Manuel'
_publ_section_title
;
 Synthesis and reactivity of electron poor allenes: formation of
 completely organic frustrated Lewis pairs.
;
_journal_issue                   30
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              9073
_journal_page_last               9082
_journal_paper_doi               10.1039/c2dt30195d
_journal_volume                  41
_journal_year                    2012
_chemical_compound_source        'methylene chloride, pentane'
_chemical_formula_moiety         'C44 H37 P2 S, F6 P'
_chemical_formula_sum            'C44 H37 F6 P3 S'
_chemical_formula_weight         804.71
_chemical_name_systematic
;
1-(4-(methyl)phenylthio)-carbo-bis(triphenyl)phosphonium
hexafluorophosphate
;
_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
_audit_block_code                AVM-AB-777-01
_audit_creation_date             2012-01-18
_cell_angle_alpha                98.106(5)
_cell_angle_beta                 97.846(5)
_cell_angle_gamma                110.584(5)
_cell_formula_units_Z            2
_cell_length_a                   10.4125(4)
_cell_length_b                   12.2494(14)
_cell_length_c                   16.5886(7)
_cell_measurement_reflns_used    53212
_cell_measurement_temperature    100
_cell_measurement_theta_max      33.0973
_cell_measurement_theta_min      2.6885
_cell_volume                     1921.0(3)
_computing_cell_refinement       'DENZO (Bruker AXS, 2006)'
_computing_data_collection       'DATCOL (Bruker AXS, 2006)'
_computing_data_reduction        'DENZO (Bruker AXS, 2006)'
_computing_molecular_graphics    'DIAMOND (Crystal Impact GbR, 2005)'
_computing_publication_material
;
OLEX2: a complete structure solution, refinement and analysis program.
Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 18.02
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker AXS Enraf-Nonius KappaCCD'
_diffrn_measurement_method       'CCD φ- and ω-scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         '0.2 x 2mm^2^ focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_av_sigmaI/netI    0.0863
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            26184
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         30.07
_diffrn_reflns_theta_min         2.69
_exptl_absorpt_coefficient_mu    0.271
_exptl_absorpt_correction_T_max  0.98476
_exptl_absorpt_correction_T_min  0.96522
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_description       prism
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.732
_refine_diff_density_rms         0.088
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     488
_refine_ls_number_reflns         10957
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.0565
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
calc w=1/[σ²(Fo²)+(0.0566P)²+1.1490P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1275
_refine_ls_wR_factor_ref         0.1464
_reflns_number_gt                7538
_reflns_number_total             10957
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2dt30195d.txt
_cod_data_source_block           7000_28
_cod_original_cell_volume        1921.0(2)
_cod_original_sg_symbol_Hall     '-p 1'
_cod_database_code               7019702
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-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
S1 S 0.94079(6) 0.57750(6) 0.14976(3) 0.01702(13) Uani 1 1 d .
P1 P 0.74951(6) 0.69490(5) 0.20850(3) 0.01343(13) Uani 1 1 d .
P2 P 0.91320(6) 0.58316(5) 0.32268(3) 0.01246(12) Uani 1 1 d .
P3 P 0.37780(7) 0.12382(6) 0.29240(4) 0.01927(14) Uani 1 1 d .
F1 F 0.49669(16) 0.06938(15) 0.30387(10) 0.0299(4) Uani 1 1 d .
F2 F 0.25886(18) 0.17876(17) 0.28228(11) 0.0379(4) Uani 1 1 d .
F3 F 0.41984(17) 0.15903(16) 0.20776(9) 0.0311(4) Uani 1 1 d .
F4 F 0.26663(17) -0.00384(15) 0.24267(10) 0.0331(4) Uani 1 1 d .
F5 F 0.48870(18) 0.25154(15) 0.34331(10) 0.0345(4) Uani 1 1 d .
F6 F 0.33658(18) 0.08939(16) 0.37818(9) 0.0319(4) Uani 1 1 d .
C1 C 0.8529(2) 0.6125(2) 0.22742(13) 0.0149(4) Uani 1 1 d .
C2 C 0.8378(3) 0.4313(2) 0.09005(14) 0.0188(5) Uani 1 1 d .
C3 C 0.9100(3) 0.3725(2) 0.04766(14) 0.0217(5) Uani 1 1 d .
H3 H 1.0066 0.4084 0.0536 0.026 Uiso 1 1 calc R
C4 C 0.8375(3) 0.2607(3) -0.00317(16) 0.0270(6) Uani 1 1 d .
H4 H 0.8863 0.2233 -0.0321 0.032 Uiso 1 1 calc R
C5 C 0.6937(3) 0.2037(3) -0.01167(15) 0.0263(6) Uani 1 1 d .
C6 C 0.6227(3) 0.2620(2) 0.03167(15) 0.0227(5) Uani 1 1 d .
H6 H 0.5266 0.2247 0.0272 0.027 Uiso 1 1 calc R
C7 C 0.6933(3) 0.3754(2) 0.08153(14) 0.0197(5) Uani 1 1 d .
H7 H 0.6440 0.4137 0.1091 0.024 Uiso 1 1 calc R
C8 C 0.6141(4) 0.0832(3) -0.06921(19) 0.0381(7) Uani 1 1 d .
H8A H 0.5165 0.0579 -0.0670 0.057 Uiso 1 1 calc R
H8B H 0.6500 0.0262 -0.0520 0.057 Uiso 1 1 calc R
H8C H 0.6254 0.0895 -0.1251 0.057 Uiso 1 1 calc R
C11 C 0.8017(2) 0.8290(2) 0.28693(13) 0.0152(4) Uani 1 1 d .
C12 C 0.9443(3) 0.8983(2) 0.31269(14) 0.0177(5) Uani 1 1 d .
H12 H 1.0094 0.8773 0.2878 0.021 Uiso 1 1 calc R
C13 C 0.9889(3) 0.9994(2) 0.37605(15) 0.0218(5) Uani 1 1 d .
H13 H 1.0838 1.0458 0.3936 0.026 Uiso 1 1 calc R
C14 C 0.8913(3) 1.0307(2) 0.41283(16) 0.0237(5) Uani 1 1 d .
H14 H 0.9215 1.0972 0.4557 0.028 Uiso 1 1 calc R
C15 C 0.7496(3) 0.9639(2) 0.38638(16) 0.0236(5) Uani 1 1 d .
H15 H 0.6849 0.9865 0.4106 0.028 Uiso 1 1 calc R
C16 C 0.7038(3) 0.8623(2) 0.32299(15) 0.0196(5) Uani 1 1 d .
H16 H 0.6086 0.8171 0.3049 0.024 Uiso 1 1 calc R
C21 C 0.5634(2) 0.6188(2) 0.20299(13) 0.0149(4) Uani 1 1 d .
C22 C 0.5144(2) 0.5271(2) 0.24636(14) 0.0172(5) Uani 1 1 d .
H22 H 0.5766 0.4995 0.2743 0.021 Uiso 1 1 calc R
C23 C 0.3720(3) 0.4773(2) 0.24759(14) 0.0209(5) Uani 1 1 d .
H23 H 0.3393 0.4165 0.2764 0.025 Uiso 1 1 calc R
C24 C 0.2792(3) 0.5184(2) 0.20590(15) 0.0223(5) Uani 1 1 d .
H24 H 0.1846 0.4860 0.2077 0.027 Uiso 1 1 calc R
C25 C 0.3265(3) 0.6078(2) 0.16136(15) 0.0214(5) Uani 1 1 d .
H25 H 0.2635 0.6338 0.1325 0.026 Uiso 1 1 calc R
C26 C 0.4681(3) 0.6583(2) 0.16007(14) 0.0191(5) Uani 1 1 d .
H26 H 0.4999 0.7184 0.1306 0.023 Uiso 1 1 calc R
C31 C 0.7642(3) 0.7410(2) 0.10974(14) 0.0177(5) Uani 1 1 d .
C32 C 0.7004(3) 0.6571(3) 0.03562(15) 0.0266(6) Uani 1 1 d .
H32 H 0.6533 0.5775 0.0368 0.032 Uiso 1 1 calc R
C33 C 0.7077(3) 0.6931(3) -0.03989(17) 0.0366(8) Uani 1 1 d .
H33 H 0.6661 0.6370 -0.0893 0.044 Uiso 1 1 calc R
C34 C 0.7764(3) 0.8116(3) -0.04231(18) 0.0390(8) Uani 1 1 d .
H34 H 0.7804 0.8352 -0.0931 0.047 Uiso 1 1 calc R
C35 C 0.8387(3) 0.8945(3) 0.03070(19) 0.0414(8) Uani 1 1 d .
H35 H 0.8844 0.9742 0.0290 0.050 Uiso 1 1 calc R
C36 C 0.8341(3) 0.8601(3) 0.10754(17) 0.0304(6) Uani 1 1 d .
H36 H 0.8773 0.9164 0.1567 0.036 Uiso 1 1 calc R
C41 C 0.8122(2) 0.5922(2) 0.40292(13) 0.0136(4) Uani 1 1 d .
C42 C 0.8149(2) 0.7025(2) 0.44134(13) 0.0163(5) Uani 1 1 d .
H42 H 0.8662 0.7716 0.4247 0.020 Uiso 1 1 calc R
C43 C 0.7406(3) 0.7088(2) 0.50444(14) 0.0193(5) Uani 1 1 d .
H43 H 0.7384 0.7815 0.5279 0.023 Uiso 1 1 calc R
C44 C 0.6701(3) 0.6073(2) 0.53235(14) 0.0194(5) Uani 1 1 d .
H44 H 0.6229 0.6124 0.5756 0.023 Uiso 1 1 calc R
C45 C 0.6696(2) 0.4974(2) 0.49605(14) 0.0189(5) Uani 1 1 d .
H45 H 0.6227 0.4294 0.5153 0.023 Uiso 1 1 calc R
C46 C 0.7394(2) 0.4894(2) 0.43093(14) 0.0166(5) Uani 1 1 d .
H46 H 0.7377 0.4159 0.4060 0.020 Uiso 1 1 calc R
C51 C 1.0910(2) 0.6820(2) 0.37371(14) 0.0156(4) Uani 1 1 d .
C52 C 1.1338(3) 0.6934(2) 0.45896(14) 0.0184(5) Uani 1 1 d .
H52 H 1.0712 0.6516 0.4891 0.022 Uiso 1 1 calc R
C53 C 1.2702(3) 0.7673(2) 0.49918(15) 0.0211(5) Uani 1 1 d .
H53 H 1.2981 0.7757 0.5561 0.025 Uiso 1 1 calc R
C54 C 1.3642(3) 0.8285(2) 0.45364(17) 0.0228(5) Uani 1 1 d .
H54 H 1.4555 0.8769 0.4802 0.027 Uiso 1 1 calc R
C55 C 1.3226(3) 0.8177(2) 0.36914(16) 0.0221(5) Uani 1 1 d .
H55 H 1.3857 0.8592 0.3391 0.027 Uiso 1 1 calc R
C56 C 1.1861(3) 0.7449(2) 0.32883(15) 0.0194(5) Uani 1 1 d .
H56 H 1.1583 0.7381 0.2720 0.023 Uiso 1 1 calc R
C61 C 0.9094(2) 0.4327(2) 0.30303(13) 0.0151(4) Uani 1 1 d .
C62 C 1.0281(3) 0.4077(2) 0.32736(15) 0.0182(5) Uani 1 1 d .
H62 H 1.1109 0.4683 0.3567 0.022 Uiso 1 1 calc R
C63 C 1.0218(3) 0.2914(2) 0.30749(15) 0.0219(5) Uani 1 1 d .
H63 H 1.1009 0.2746 0.3231 0.026 Uiso 1 1 calc R
C64 C 0.8982(3) 0.2007(2) 0.26453(15) 0.0229(5) Uani 1 1 d .
H64 H 0.8953 0.1236 0.2504 0.027 Uiso 1 1 calc R
C65 C 0.7782(3) 0.2245(2) 0.24235(15) 0.0198(5) Uani 1 1 d .
H65 H 0.6946 0.1632 0.2150 0.024 Uiso 1 1 calc R
C66 C 0.7843(3) 0.3401(2) 0.26139(14) 0.0176(5) Uani 1 1 d .
H66 H 0.7045 0.3563 0.2464 0.021 Uiso 1 1 calc R
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'
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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 1.00 0.00 0.0350
1.00 -1.00 0.00 0.0350
0.00 0.00 -1.00 0.0700
0.00 0.00 1.00 0.0700
0.00 1.00 -1.00 0.0600
0.00 -1.00 1.00 0.0600
0.00 1.00 0.00 0.0700
0.00 -1.00 0.00 0.0700
1.00 -1.00 -1.00 0.0400
1.00 -1.00 1.00 0.0400
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
P1 C1 S1 118.86(12) y
P1 C1 P2 127.91(13) y
P2 C1 S1 111.87(13) y
F1 P3 F2 179.20(10) y
F1 P3 F4 90.09(10) y
F1 P3 F5 89.97(10) y
F1 P3 F6 89.57(9) y
F2 P3 F5 89.66(10) y
F2 P3 F6 89.72(9) y
F3 P3 F1 90.36(9) y
F3 P3 F2 90.35(9) y
F3 P3 F4 90.87(9) y
F3 P3 F5 89.83(9) y
F3 P3 F6 179.49(11) y
F4 P3 F2 90.27(10) y
F4 P3 F5 179.30(10) y
F4 P3 F6 89.64(9) y
F5 P3 F6 89.66(9) y
C1 S1 C2 108.96(11) y
C1 P1 C11 112.31(11) y
C1 P1 C21 115.98(11) y
C1 P1 C31 110.42(11) y
C1 P2 C41 116.07(11) y
C1 P2 C51 114.69(11) y
C1 P2 C61 107.52(11) y
C2 C7 C6 120.0(2) y
C3 C2 S1 116.1(2) y
C3 C4 C5 121.3(2) y
C4 C3 C2 120.1(3) y
C4 C5 C6 118.3(3) y
C4 C5 C8 121.2(3) y
C6 C5 C8 120.5(3) y
C7 C2 S1 124.72(19) y
C7 C2 C3 119.2(2) y
C7 C6 C5 121.2(3) y
C11 P1 C21 105.28(11) y
C11 P1 C31 106.77(11) y
C11 C12 C13 119.7(2) y
C11 C16 C15 119.7(2) y
C12 C11 P1 118.13(18) y
C12 C11 C16 120.1(2) y
C14 C13 C12 119.9(2) y
C14 C15 C16 119.8(2) y
C15 C14 C13 120.7(2) y
C16 C11 P1 121.72(19) y
C21 P1 C31 105.45(11) y
C22 C21 P1 120.82(18) y
C22 C21 C26 119.5(2) y
C23 C22 C21 119.9(2) y
C23 C24 C25 120.5(2) y
C24 C23 C22 120.0(2) y
C25 C26 C21 120.2(2) y
C26 C21 P1 119.53(17) y
C26 C25 C24 119.9(2) y
C31 C36 C35 119.4(3) y
C32 C31 P1 119.7(2) y
C33 C32 C31 119.7(3) y
C34 C33 C32 120.5(3) y
C34 C35 C36 120.7(3) y
C35 C34 C33 119.8(2) y
C36 C31 P1 120.35(19) y
C36 C31 C32 119.9(2) y
C41 P2 C51 103.35(10) y
C42 C41 P2 120.45(16) y
C42 C41 C46 119.4(2) y
C43 C42 C41 120.0(2) y
C43 C44 C45 120.3(2) y
C44 C43 C42 120.2(2) y
C45 C46 C41 120.1(2) y
C46 C41 P2 119.95(18) y
C46 C45 C44 119.9(2) y
C51 C52 C53 120.3(2) y
C52 C51 P2 119.29(17) y
C52 C51 C56 119.4(2) y
C54 C53 C52 119.7(2) y
C54 C55 C56 120.2(2) y
C55 C54 C53 120.3(2) y
C55 C56 C51 120.1(2) y
C56 C51 P2 121.27(18) y
C61 P2 C41 107.03(10) y
C61 P2 C51 107.68(11) y
C62 C61 P2 121.73(19) y
C62 C61 C66 119.6(2) y
C63 C62 C61 119.6(2) y
C63 C64 C65 120.4(2) y
C64 C63 C62 120.3(2) y
C65 C66 C61 120.6(2) y
C66 C61 P2 118.66(18) y
C66 C65 C64 119.5(2) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C1 1.767(2) y
S1 C2 1.788(3) y
P1 C1 1.743(2) y
P1 C11 1.806(2) y
P1 C21 1.813(2) y
P1 C31 1.815(2) y
P2 C1 1.752(2) y
P2 C41 1.820(2) y
P2 C51 1.822(2) y
P2 C61 1.811(2) y
P3 F1 1.6016(17) y
P3 F2 1.6050(17) y
P3 F3 1.5984(15) y
P3 F4 1.6026(17) y
P3 F5 1.6078(17) y
P3 F6 1.6111(15) y
C2 C3 1.400(3) y
C2 C7 1.394(4) y
C3 C4 1.389(4) y
C4 C5 1.389(4) y
C5 C6 1.395(4) y
C5 C8 1.517(4) y
C6 C7 1.395(4) y
C11 C12 1.395(3) y
C11 C16 1.398(3) y
C12 C13 1.396(4) y
C13 C14 1.389(4) y
C14 C15 1.382(4) y
C15 C16 1.400(4) y
C21 C22 1.402(3) y
C21 C26 1.402(3) y
C22 C23 1.395(3) y
C23 C24 1.387(4) y
C24 C25 1.392(3) y
C25 C26 1.389(3) y
C31 C32 1.396(4) y
C31 C36 1.391(4) y
C32 C33 1.388(4) y
C33 C34 1.385(5) y
C34 C35 1.376(5) y
C35 C36 1.399(3) y
C41 C42 1.399(3) y
C41 C46 1.402(3) y
C42 C43 1.393(3) y
C43 C44 1.383(3) y
C44 C45 1.393(4) y
C45 C46 1.393(3) y
C51 C52 1.395(3) y
C51 C56 1.398(3) y
C52 C53 1.396(3) y
C53 C54 1.392(4) y
C54 C55 1.383(4) y
C55 C56 1.394(3) y
C61 C62 1.396(3) y
C61 C66 1.399(3) y
C62 C63 1.391(3) y
C63 C64 1.386(4) y
C64 C65 1.394(4) y
C65 C66 1.383(3) y
