#------------------------------------------------------------------------------
#$Date: 2020-10-06 12:18:46 +0200 (mar 06 de oct de 2020) $
#$Revision: 257792 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/96/7059667.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_7059667
loop_
_publ_author_name
'Ling, Irene'
'Skelton, Brian W.'
'Sobolev, Alexandre N.'
'Alias, Yatimah'
'Khor, Zong Chin'
'Raston, Colin L.'
_publ_section_title
;
 Effect of anions on the solid-state interplay of symmetric and
 unsymmetric phosphonium cations
;
_journal_issue                   25
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              10220
_journal_page_last               10228
_journal_paper_doi               10.1039/D0NJ01975E
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C24 H20 P, C2 F6 N O4 S2'
_chemical_formula_sum            'C26 H20 F6 N O4 P S2'
_chemical_formula_weight         619.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-05-17 deposited with the CCDC.	2020-05-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.053(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.2823(3)
_cell_length_b                   7.3469(1)
_cell_length_c                   16.0521(2)
_cell_measurement_reflns_used    7049
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.137
_cell_measurement_theta_min      4.589
_cell_volume                     2607.94(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'X-Seed v. 4.0 (Barbour, 2001)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2015/1 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4738
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini-R Ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0146134
_diffrn_orient_matrix_UB_12      0.0700085
_diffrn_orient_matrix_UB_13      -0.0906416
_diffrn_orient_matrix_UB_21      -0.0034456
_diffrn_orient_matrix_UB_22      -0.1975499
_diffrn_orient_matrix_UB_23      -0.0324369
_diffrn_orient_matrix_UB_31      -0.0680487
_diffrn_orient_matrix_UB_32      -0.0050882
_diffrn_orient_matrix_UB_33      0.0089900
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'fine-focus sealed X-ray tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9481
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.246
_diffrn_reflns_theta_max         67.246
_diffrn_reflns_theta_min         3.998
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.152
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89168
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_description       prism
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         2314
_refine_ls_number_restraints     110
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0297
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0350P)²+3.7500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0722
_refine_ls_wR_factor_ref         0.0746
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2150
_reflns_number_total             2314
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0nj01975e1.cif
_cod_data_source_block           110301A
_cod_depositor_comments
;Adding full bibliography for 7059666--7059672.cif.

 Adding full bibliography for 7059666--7059672.cif.
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7059667
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.616
_shelx_estimated_absorpt_t_max   0.743
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.000000 0.35661(7) 0.250000 0.01578(14) Uani 1 2 d S T P . .
C11 C 0.04811(6) 0.5028(2) 0.31843(9) 0.0185(3) Uani 1 1 d . . . . .
C12 C 0.05328(7) 0.4855(2) 0.40564(9) 0.0218(3) Uani 1 1 d . . . . .
H12 H 0.031851 0.392691 0.430730 0.026 Uiso 1 1 calc R U . . .
C13 C 0.09018(7) 0.6058(2) 0.45528(10) 0.0270(4) Uani 1 1 d . . . . .
H13 H 0.093680 0.595787 0.514685 0.032 Uiso 1 1 calc R U . . .
C14 C 0.12190(7) 0.7403(2) 0.41883(11) 0.0278(4) Uani 1 1 d . . . . .
H14 H 0.147483 0.820797 0.453216 0.033 Uiso 1 1 calc R U . . .
C15 C 0.11633(7) 0.7574(2) 0.33201(11) 0.0271(4) Uani 1 1 d . . . . .
H15 H 0.137971 0.850011 0.307111 0.032 Uiso 1 1 calc R U . . .
C16 C 0.07937(7) 0.6401(2) 0.28191(10) 0.0237(3) Uani 1 1 d . . . . .
H16 H 0.075232 0.652766 0.222584 0.028 Uiso 1 1 calc R U . . .
C21 C 0.04268(7) 0.2099(2) 0.19001(9) 0.0178(3) Uani 1 1 d . . . . .
C22 C 0.10518(7) 0.2247(2) 0.19142(9) 0.0217(3) Uani 1 1 d . . . . .
H22 H 0.127149 0.314983 0.224815 0.026 Uiso 1 1 calc R U . . .
C23 C 0.13488(7) 0.1050(2) 0.14307(10) 0.0268(4) Uani 1 1 d . . . . .
H23 H 0.177423 0.113938 0.143217 0.032 Uiso 1 1 calc R U . . .
C24 C 0.10269(8) -0.0269(2) 0.09479(10) 0.0269(4) Uani 1 1 d . . . . .
H24 H 0.123232 -0.106590 0.061251 0.032 Uiso 1 1 calc R U . . .
C25 C 0.04081(8) -0.0436(2) 0.09501(10) 0.0252(3) Uani 1 1 d . . . . .
H25 H 0.019242 -0.136130 0.062617 0.030 Uiso 1 1 calc R U . . .
C26 C 0.01031(7) 0.0744(2) 0.14237(9) 0.0214(3) Uani 1 1 d . . . . .
H26 H -0.032164 0.063541 0.142519 0.026 Uiso 1 1 calc R U . . .
S1 S 0.2793(2) 0.7513(8) 0.0813(4) 0.0335(11) Uani 0.5 1 d . U P A -1
C1 C 0.2326(6) 0.5717(16) 0.1359(8) 0.0268(8) Uani 0.5 1 d . U P A -1
N1 N 0.23182(11) 0.8414(3) 0.01576(15) 0.0208(5) Uani 0.5 1 d . . P A -1
O1 O 0.33127(11) 0.6752(3) 0.06462(18) 0.0240(5) Uani 0.5 1 d . . P A -1
O2 O 0.28592(11) 0.8949(3) 0.15471(14) 0.0317(5) Uani 0.5 1 d . . P A -1
F1 F 0.26708(10) 0.5156(3) 0.20179(13) 0.0392(5) Uani 0.5 1 d . . P A -1
F2 F 0.22695(12) 0.4396(3) 0.07833(16) 0.0435(5) Uani 0.5 1 d . . P A -1
F3 F 0.18281(12) 0.6341(5) 0.1504(2) 0.0541(8) Uani 0.5 1 d . . P A -1
O1' O 0.16165(11) 0.8097(4) -0.11234(19) 0.0282(6) Uani 0.5 1 d . . P A -1
O2' O 0.24521(11) 0.5868(3) -0.09042(14) 0.0287(5) Uani 0.5 1 d . . P A -1
F1' F 0.32668(10) 0.9038(4) -0.10462(16) 0.0321(5) Uani 0.5 1 d . . P A -1
F2' F 0.26202(12) 0.8710(5) -0.21428(14) 0.0584(7) Uani 0.5 1 d . . P A -1
F3' F 0.25220(11) 1.0890(3) -0.1274(2) 0.0484(6) Uani 0.5 1 d . . P A -1
S2 S 0.22268(19) 0.7537(6) -0.0847(3) 0.0208(8) Uani 0.5 1 d . . P A -1
C2 C 0.2643(6) 0.9118(17) -0.1295(8) 0.0285(9) Uani 0.5 1 d . . P A -1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
C21 P1 C21 106.13(10) . 2 ?
C21 P1 C11 110.32(7) . 2 ?
C21 P1 C11 111.84(7) 2 2 ?
C21 P1 C11 111.84(7) . . ?
C21 P1 C11 110.32(7) 2 . ?
C11 P1 C11 106.49(10) 2 . ?
C16 C11 C12 120.19(14) . . ?
C16 C11 P1 117.84(11) . . ?
C12 C11 P1 121.94(12) . . ?
C13 C12 C11 119.17(15) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C14 C13 C12 120.52(15) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 120.06(15) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C16 C15 C14 120.07(15) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C11 119.97(15) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
C22 C21 C26 120.73(14) . . ?
C22 C21 P1 122.58(12) . . ?
C26 C21 P1 116.67(11) . . ?
C23 C22 C21 118.92(15) . . ?
C23 C22 H22 120.5 . . ?
C21 C22 H22 120.5 . . ?
C24 C23 C22 120.33(15) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C25 C24 C23 120.51(15) . . ?
C25 C24 H24 119.7 . . ?
C23 C24 H24 119.7 . . ?
C24 C25 C26 120.14(15) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C25 C26 C21 119.34(14) . . ?
C25 C26 H26 120.3 . . ?
C21 C26 H26 120.3 . . ?
O1 S1 N1 125.3(5) . . ?
O1 S1 O2 115.1(4) . . ?
N1 S1 O2 102.5(3) . . ?
O1 S1 C1 109.2(5) . . ?
N1 S1 C1 103.7(5) . . ?
O2 S1 C1 97.1(5) . . ?
F3 C1 F1 114.6(10) . . ?
F3 C1 F2 112.7(10) . . ?
F1 C1 F2 109.3(9) . . ?
F3 C1 S1 111.7(8) . . ?
F1 C1 S1 106.6(8) . . ?
F2 C1 S1 101.0(7) . . ?
S1 N1 S2 117.9(3) . . ?
O2' S2 O1' 126.3(4) . . ?
O2' S2 C2 111.7(6) . . ?
O1' S2 C2 102.6(5) . . ?
O2' S2 N1 113.9(3) . . ?
O1' S2 N1 100.4(3) . . ?
C2 S2 N1 97.6(6) . . ?
F3' C2 F2' 104.6(7) . . ?
F3' C2 F1' 103.4(8) . . ?
F2' C2 F1' 100.7(8) . . ?
F3' C2 S2 122.4(9) . . ?
F2' C2 S2 108.1(8) . . ?
F1' C2 S2 115.2(7) . . ?
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 C21 1.7941(15) . ?
P1 C21 1.7941(15) 2 ?
P1 C11 1.7943(15) 2 ?
P1 C11 1.7943(15) . ?
C11 C16 1.395(2) . ?
C11 C12 1.396(2) . ?
C12 C13 1.390(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.390(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.380(2) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C22 1.394(2) . ?
C21 C26 1.400(2) . ?
C22 C23 1.393(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.385(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.385(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.385(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
S1 O1 1.342(6) . ?
S1 N1 1.546(6) . ?
S1 O2 1.575(7) . ?
S1 C1 1.954(10) . ?
C1 F3 1.248(13) . ?
C1 F1 1.295(14) . ?
C1 F2 1.336(15) . ?
N1 S2 1.725(6) . ?
O1' S2 1.438(4) . ?
O2' S2 1.333(5) . ?
F1' C2 1.399(13) . ?
F2' C2 1.389(14) . ?
F3' C2 1.331(13) . ?
S2 C2 1.700(10) . ?
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C21 P1 C11 C16 69.33(13) . . . . ?
C21 P1 C11 C16 -172.79(11) 2 . . . ?
C11 P1 C11 C16 -51.24(10) 2 . . . ?
C21 P1 C11 C12 -112.62(13) . . . . ?
C21 P1 C11 C12 5.26(15) 2 . . . ?
C11 P1 C11 C12 126.81(14) 2 . . . ?
C16 C11 C12 C13 -0.4(2) . . . . ?
P1 C11 C12 C13 -178.43(12) . . . . ?
C11 C12 C13 C14 -0.6(2) . . . . ?
C12 C13 C14 C15 0.9(2) . . . . ?
C13 C14 C15 C16 -0.3(2) . . . . ?
C14 C15 C16 C11 -0.7(2) . . . . ?
C12 C11 C16 C15 1.1(2) . . . . ?
P1 C11 C16 C15 179.16(12) . . . . ?
C21 P1 C21 C22 -126.62(14) 2 . . . ?
C11 P1 C21 C22 112.05(12) 2 . . . ?
C11 P1 C21 C22 -6.27(14) . . . . ?
C21 P1 C21 C26 51.86(10) 2 . . . ?
C11 P1 C21 C26 -69.47(13) 2 . . . ?
C11 P1 C21 C26 172.21(11) . . . . ?
C26 C21 C22 C23 1.5(2) . . . . ?
P1 C21 C22 C23 179.87(11) . . . . ?
C21 C22 C23 C24 -0.3(2) . . . . ?
C22 C23 C24 C25 -1.1(2) . . . . ?
C23 C24 C25 C26 1.3(2) . . . . ?
C24 C25 C26 C21 -0.2(2) . . . . ?
C22 C21 C26 C25 -1.2(2) . . . . ?
P1 C21 C26 C25 -179.72(11) . . . . ?
O1 S1 N1 S2 32.7(7) . . . . ?
O2 S1 N1 S2 166.24(18) . . . . ?
C1 S1 N1 S2 -93.2(6) . . . . ?
S1 N1 S2 O2' 17.7(6) . . . . ?
S1 N1 S2 O1' 155.4(2) . . . . ?
S1 N1 S2 C2 -100.2(6) . . . . ?
O2' S2 C2 F3' -176.4(9) . . . . ?
O1' S2 C2 F3' 45.6(12) . . . . ?
N1 S2 C2 F3' -56.8(11) . . . . ?
O2' S2 C2 F2' 62.2(9) . . . . ?
O1' S2 C2 F2' -75.8(9) . . . . ?
N1 S2 C2 F2' -178.3(7) . . . . ?
O2' S2 C2 F1' -49.5(11) . . . . ?
O1' S2 C2 F1' 172.6(8) . . . . ?
N1 S2 C2 F1' 70.1(10) . . . . ?
