#------------------------------------------------------------------------------
#$Date: 2016-03-26 20:57:10 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180457 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/26/7212635.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_7212635
loop_
_publ_author_name
'Ling, Irene'
'Alias, Yatimah'
'Sobolev, Alexandre N.'
'Raston, Colin L.'
_publ_section_title
;
 Hirshfeld surface analysis of phosphonium salts
;
_journal_issue                   12
_journal_name_full               CrystEngComm
_journal_page_first              4321
_journal_paper_doi               10.1039/c002832k
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C44 H38 P2, 2(C2 F6 N O4 S2)'
_chemical_formula_sum            'C48 H38 F12 N2 O8 P2 S4'
_chemical_formula_weight         1188.98
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                107.982(5)
_cell_angle_beta                 90.275(4)
_cell_angle_gamma                101.322(4)
_cell_formula_units_Z            1
_cell_length_a                   9.5923(5)
_cell_length_b                   11.4243(6)
_cell_length_c                   12.2741(6)
_cell_measurement_reflns_used    6550
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.8
_cell_measurement_theta_min      3.36
_cell_volume                     1251.37(12)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_data_collection
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
;
_computing_molecular_graphics    'X-Seed 2.0 (Barbour, 2001)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4738
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.889
_diffrn_measurement_device_type  'Oxford Diffraction Gemini-R Ultra, Ruby CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_sigmaI/netI    0.0545
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15083
_diffrn_reflns_theta_full        29.50
_diffrn_reflns_theta_max         31.91
_diffrn_reflns_theta_min         3.36
_exptl_absorpt_coefficient_mu    0.355
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9616
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET)
(compiled Jun 10 2008,16:49:55)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             606
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         7654
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0401
_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)+(0.0590P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1089
_reflns_number_gt                5446
_reflns_number_total             7654
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c002832k.txt
_cod_data_source_block           170608n1#2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        1251.37(11)
_cod_database_code               7212635
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
P1 P 0.13997(4) 0.24856(4) 0.52034(3) 0.01200(9) Uani 1 1 d .
C10 C 0.20439(15) 0.41455(14) 0.53902(13) 0.0132(3) Uani 1 1 d .
H10A H 0.1449 0.4385 0.4867 0.016 Uiso 1 1 calc R
H10B H 0.1890 0.4630 0.6185 0.016 Uiso 1 1 calc R
C11 C 0.15433(16) 0.15380(14) 0.37562(13) 0.0149(3) Uani 1 1 d .
C12 C 0.03275(17) 0.08836(15) 0.30294(14) 0.0182(3) Uani 1 1 d .
H12 H -0.0592 0.0901 0.3310 0.022 Uiso 1 1 calc R
C13 C 0.0464(2) 0.02045(16) 0.18911(15) 0.0248(4) Uani 1 1 d .
H13 H -0.0362 -0.0240 0.1396 0.030 Uiso 1 1 calc R
C14 C 0.1802(2) 0.01787(17) 0.14834(15) 0.0281(4) Uani 1 1 d .
H14 H 0.1892 -0.0282 0.0706 0.034 Uiso 1 1 calc R
C15 C 0.3017(2) 0.08218(16) 0.22028(15) 0.0255(4) Uani 1 1 d .
H15 H 0.3933 0.0799 0.1917 0.031 Uiso 1 1 calc R
C16 C 0.28920(18) 0.14969(15) 0.33382(15) 0.0202(3) Uani 1 1 d .
H16 H 0.3723 0.1931 0.3831 0.024 Uiso 1 1 calc R
C21 C 0.23813(15) 0.20130(14) 0.61819(13) 0.0138(3) Uani 1 1 d .
C22 C 0.28003(16) 0.08564(15) 0.58421(14) 0.0175(3) Uani 1 1 d .
H22 H 0.2636 0.0330 0.5065 0.021 Uiso 1 1 calc R
C23 C 0.34635(17) 0.04820(16) 0.66550(15) 0.0216(4) Uani 1 1 d .
H23 H 0.3746 -0.0306 0.6431 0.026 Uiso 1 1 calc R
C24 C 0.37119(17) 0.12499(16) 0.77828(15) 0.0205(3) Uani 1 1 d .
H24 H 0.4164 0.0988 0.8331 0.025 Uiso 1 1 calc R
C25 C 0.33054(17) 0.24010(16) 0.81192(14) 0.0204(3) Uani 1 1 d .
H25 H 0.3485 0.2927 0.8895 0.024 Uiso 1 1 calc R
C26 C 0.26368(17) 0.27891(15) 0.73279(14) 0.0173(3) Uani 1 1 d .
H26 H 0.2353 0.3576 0.7561 0.021 Uiso 1 1 calc R
C31 C -0.04206(15) 0.23676(14) 0.55645(13) 0.0132(3) Uani 1 1 d .
C32 C -0.08720(16) 0.20110(14) 0.65187(13) 0.0156(3) Uani 1 1 d .
H32 H -0.0236 0.1749 0.6946 0.019 Uiso 1 1 calc R
C33 C -0.22502(17) 0.20416(15) 0.68390(14) 0.0189(3) Uani 1 1 d .
H33 H -0.2554 0.1812 0.7494 0.023 Uiso 1 1 calc R
C34 C -0.31887(17) 0.24064(15) 0.62079(14) 0.0195(3) Uani 1 1 d .
H34 H -0.4133 0.2425 0.6431 0.023 Uiso 1 1 calc R
C35 C -0.27479(17) 0.27456(15) 0.52482(14) 0.0172(3) Uani 1 1 d .
H35 H -0.3397 0.2982 0.4810 0.021 Uiso 1 1 calc R
C36 C -0.13660(16) 0.27395(14) 0.49308(13) 0.0143(3) Uani 1 1 d .
H36 H -0.1061 0.2987 0.4285 0.017 Uiso 1 1 calc R
C41 C 0.35830(15) 0.45499(13) 0.51815(13) 0.0123(3) Uani 1 1 d .
C42 C 0.39629(16) 0.45958(14) 0.40979(13) 0.0143(3) Uani 1 1 d .
H42 H 0.3255 0.4319 0.3478 0.017 Uiso 1 1 calc R
C43 C 0.46376(16) 0.49588(14) 0.60808(13) 0.0145(3) Uani 1 1 d .
H43 H 0.4392 0.4931 0.6823 0.017 Uiso 1 1 calc R
N1 N 0.87913(14) 0.26120(13) 0.11796(11) 0.0185(3) Uani 1 1 d .
S1 S 0.72143(4) 0.23009(4) 0.15030(3) 0.01721(10) Uani 1 1 d .
O11 O 0.69647(12) 0.29405(12) 0.26673(10) 0.0223(3) Uani 1 1 d .
O12 O 0.66624(13) 0.09793(12) 0.10336(11) 0.0279(3) Uani 1 1 d .
C1 C 0.62128(17) 0.29564(17) 0.06405(14) 0.0211(4) Uani 1 1 d .
F11 F 0.48212(10) 0.25868(12) 0.07176(10) 0.0362(3) Uani 1 1 d .
F12 F 0.64763(12) 0.25458(11) -0.04595(9) 0.0342(3) Uani 1 1 d .
F13 F 0.65202(12) 0.42040(10) 0.09852(10) 0.0326(3) Uani 1 1 d .
S2 S 0.98615(4) 0.38608(4) 0.18921(3) 0.01692(10) Uani 1 1 d .
O21 O 1.05301(13) 0.37617(13) 0.28990(11) 0.0272(3) Uani 1 1 d .
O22 O 0.93975(13) 0.50072(11) 0.19986(10) 0.0248(3) Uani 1 1 d .
C2 C 1.1245(2) 0.37777(19) 0.08661(17) 0.0287(4) Uani 1 1 d .
F21 F 1.23186(13) 0.47538(13) 0.13038(12) 0.0505(4) Uani 1 1 d .
F22 F 1.07684(14) 0.38146(12) -0.01271(10) 0.0434(3) Uani 1 1 d .
F23 F 1.17353(12) 0.27281(12) 0.06823(11) 0.0418(3) 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'
N N 0.0061 0.0033 '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
C21 P1 C31 109.40(7) .
C21 P1 C11 109.86(7) .
C31 P1 C11 111.71(7) .
C21 P1 C10 110.15(7) .
C31 P1 C10 104.50(7) .
C11 P1 C10 111.09(7) .
C41 C10 P1 116.96(10) .
C41 C10 H10A 108.1 .
P1 C10 H10A 108.1 .
C41 C10 H10B 108.1 .
P1 C10 H10B 108.1 .
H10A C10 H10B 107.3 .
C12 C11 C16 119.63(15) .
C12 C11 P1 120.94(12) .
C16 C11 P1 119.38(12) .
C13 C12 C11 119.94(16) .
C13 C12 H12 120.0 .
C11 C12 H12 120.0 .
C14 C13 C12 119.98(17) .
C14 C13 H13 120.0 .
C12 C13 H13 120.0 .
C13 C14 C15 120.42(16) .
C13 C14 H14 119.8 .
C15 C14 H14 119.8 .
C16 C15 C14 120.03(16) .
C16 C15 H15 120.0 .
C14 C15 H15 120.0 .
C15 C16 C11 119.99(16) .
C15 C16 H16 120.0 .
C11 C16 H16 120.0 .
C22 C21 C26 120.04(14) .
C22 C21 P1 121.23(12) .
C26 C21 P1 118.57(12) .
C23 C22 C21 119.32(15) .
C23 C22 H22 120.3 .
C21 C22 H22 120.3 .
C24 C23 C22 120.40(16) .
C24 C23 H23 119.8 .
C22 C23 H23 119.8 .
C23 C24 C25 120.33(15) .
C23 C24 H24 119.8 .
C25 C24 H24 119.8 .
C24 C25 C26 120.29(16) .
C24 C25 H25 119.9 .
C26 C25 H25 119.9 .
C25 C26 C21 119.62(15) .
C25 C26 H26 120.2 .
C21 C26 H26 120.2 .
C32 C31 C36 119.93(14) .
C32 C31 P1 121.07(12) .
C36 C31 P1 118.79(11) .
C33 C32 C31 119.74(14) .
C33 C32 H32 120.1 .
C31 C32 H32 120.1 .
C32 C33 C34 120.30(14) .
C32 C33 H33 119.9 .
C34 C33 H33 119.9 .
C33 C34 C35 120.08(14) .
C33 C34 H34 120.0 .
C35 C34 H34 120.0 .
C36 C35 C34 120.17(14) .
C36 C35 H35 119.9 .
C34 C35 H35 119.9 .
C35 C36 C31 119.77(14) .
C35 C36 H36 120.1 .
C31 C36 H36 120.1 .
C42 C41 C43 118.91(13) .
C42 C41 C10 120.26(13) .
C43 C41 C10 120.70(13) .
C43 C42 C41 120.50(13) 2_666
C43 C42 H42 119.8 2_666
C41 C42 H42 119.8 .
C42 C43 C41 120.59(14) 2_666
C42 C43 H43 119.7 2_666
C41 C43 H43 119.7 .
S1 N1 S2 121.44(9) .
O12 S1 O11 119.08(8) .
O12 S1 N1 109.38(8) .
O11 S1 N1 114.94(7) .
O12 S1 C1 102.90(8) .
O11 S1 C1 104.26(8) .
N1 S1 C1 104.27(7) .
F13 C1 F12 108.25(14) .
F13 C1 F11 107.85(14) .
F12 C1 F11 107.77(13) .
F13 C1 S1 112.55(11) .
F12 C1 S1 110.74(12) .
F11 C1 S1 109.52(11) .
O22 S2 O21 117.19(8) .
O22 S2 N1 115.53(8) .
O21 S2 N1 113.33(8) .
O22 S2 C2 105.93(8) .
O21 S2 C2 104.67(8) .
N1 S2 C2 97.03(8) .
F22 C2 F23 108.28(16) .
F22 C2 F21 108.93(15) .
F23 C2 F21 108.45(16) .
F22 C2 S2 111.69(13) .
F23 C2 S2 111.09(12) .
F21 C2 S2 108.33(13) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1 C21 1.7915(15) .
P1 C31 1.7932(15) .
P1 C11 1.7944(16) .
P1 C10 1.8168(15) .
C10 C41 1.506(2) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C12 1.397(2) .
C11 C16 1.398(2) .
C12 C13 1.394(2) .
C12 H12 0.9500 .
C13 C14 1.382(3) .
C13 H13 0.9500 .
C14 C15 1.390(3) .
C14 H14 0.9500 .
C15 C16 1.388(2) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C21 C22 1.397(2) .
C21 C26 1.402(2) .
C22 C23 1.396(2) .
C22 H22 0.9500 .
C23 C24 1.381(2) .
C23 H23 0.9500 .
C24 C25 1.385(2) .
C24 H24 0.9500 .
C25 C26 1.387(2) .
C25 H25 0.9500 .
C26 H26 0.9500 .
C31 C32 1.398(2) .
C31 C36 1.399(2) .
C32 C33 1.385(2) .
C32 H32 0.9500 .
C33 C34 1.387(2) .
C33 H33 0.9500 .
C34 C35 1.392(2) .
C34 H34 0.9500 .
C35 C36 1.384(2) .
C35 H35 0.9500 .
C36 H36 0.9500 .
C41 C42 1.395(2) .
C41 C43 1.395(2) .
C42 C43 1.383(2) 2_666
C42 H42 0.9500 .
C43 C42 1.383(2) 2_666
C43 H43 0.9500 .
N1 S1 1.5665(14) .
N1 S2 1.5811(14) .
S1 O12 1.4276(13) .
S1 O11 1.4354(12) .
S1 C1 1.8349(17) .
C1 F13 1.326(2) .
C1 F12 1.3288(19) .
C1 F11 1.3317(18) .
S2 O22 1.4333(13) .
S2 O21 1.4348(12) .
S2 C2 1.8299(18) .
C2 F22 1.316(2) .
C2 F23 1.328(2) .
C2 F21 1.329(2) .
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_4
C21 P1 C10 C41 60.72(13) .
C31 P1 C10 C41 178.13(11) .
C11 P1 C10 C41 -61.25(13) .
C21 P1 C11 C12 125.60(13) .
C31 P1 C11 C12 4.00(15) .
C10 P1 C11 C12 -112.27(13) .
C21 P1 C11 C16 -57.03(14) .
C31 P1 C11 C16 -178.63(12) .
C10 P1 C11 C16 65.11(14) .
C16 C11 C12 C13 -0.6(2) .
P1 C11 C12 C13 176.76(12) .
C11 C12 C13 C14 0.0(2) .
C12 C13 C14 C15 0.3(3) .
C13 C14 C15 C16 -0.1(3) .
C14 C15 C16 C11 -0.5(2) .
C12 C11 C16 C15 0.8(2) .
P1 C11 C16 C15 -176.58(13) .
C31 P1 C21 C22 106.10(13) .
C11 P1 C21 C22 -16.87(15) .
C10 P1 C21 C22 -139.56(12) .
C31 P1 C21 C26 -69.35(13) .
C11 P1 C21 C26 167.68(12) .
C10 P1 C21 C26 44.98(14) .
C26 C21 C22 C23 0.4(2) .
P1 C21 C22 C23 -174.94(12) .
C21 C22 C23 C24 -0.4(2) .
C22 C23 C24 C25 0.0(2) .
C23 C24 C25 C26 0.4(2) .
C24 C25 C26 C21 -0.4(2) .
C22 C21 C26 C25 0.0(2) .
P1 C21 C26 C25 175.46(12) .
C21 P1 C31 C32 2.86(15) .
C11 P1 C31 C32 124.73(13) .
C10 P1 C31 C32 -115.07(13) .
C21 P1 C31 C36 177.61(12) .
C11 P1 C31 C36 -60.52(14) .
C10 P1 C31 C36 59.68(14) .
C36 C31 C32 C33 -0.7(2) .
P1 C31 C32 C33 173.97(12) .
C31 C32 C33 C34 0.9(2) .
C32 C33 C34 C35 -0.1(2) .
C33 C34 C35 C36 -1.0(2) .
C34 C35 C36 C31 1.2(2) .
C32 C31 C36 C35 -0.4(2) .
P1 C31 C36 C35 -175.19(12) .
P1 C10 C41 C42 92.27(15) .
P1 C10 C41 C43 -91.78(16) .
C43 C41 C42 C43 -0.1(2) 2_666
C10 C41 C42 C43 175.94(14) 2_666
C42 C41 C43 C42 0.1(2) 2_666
C10 C41 C43 C42 -175.92(14) 2_666
S2 N1 S1 O12 -158.62(9) .
S2 N1 S1 O11 -21.59(13) .
S2 N1 S1 C1 91.89(11) .
O12 S1 C1 F13 176.72(12) .
O11 S1 C1 F13 51.79(13) .
N1 S1 C1 F13 -69.11(13) .
O12 S1 C1 F12 -61.95(13) .
O11 S1 C1 F12 173.11(11) .
N1 S1 C1 F12 52.22(13) .
O12 S1 C1 F11 56.76(13) .
O11 S1 C1 F11 -68.17(13) .
N1 S1 C1 F11 170.93(12) .
S1 N1 S2 O22 -55.54(12) .
S1 N1 S2 O21 83.69(11) .
S1 N1 S2 C2 -166.98(10) .
O22 S2 C2 F22 -57.67(16) .
O21 S2 C2 F22 177.86(13) .
N1 S2 C2 F22 61.46(15) .
O22 S2 C2 F23 -178.68(13) .
O21 S2 C2 F23 56.86(16) .
N1 S2 C2 F23 -59.55(15) .
O22 S2 C2 F21 62.31(14) .
O21 S2 C2 F21 -62.16(14) .
N1 S2 C2 F21 -178.56(13) .
