Synthesis and structural trends in a series of simple tetraalkylphosphonium salts
Gawraczyński, Jakub; Leszczyński, Piotr J.; Cyrański, Michał K.; Dobrzycki, Łukasz; Koźmiński, Wiktor; Fijałkowski, Karol J.; Grochala, Wojciech; Jaroń, Tomasz; CrystEngComm 26 (2024) 2673–2682; doi:10.1039/D4CE00210E

data_7248503
_publ_section_title
;
 Synthesis and structural trends in a series of simple
 tetraalkylphosphonium salts
;
_journal_issue                   20
_journal_name_full               CrystEngComm
_journal_page_first              2673
_journal_page_last               2682
_journal_paper_doi               10.1039/D4CE00210E
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         '2(C8 H20 P), O4 S'
_chemical_formula_sum            'C16 H40 O4 P2 S'
_chemical_formula_weight         390.507
_chemical_name_systematic        'Tetrabutylphosphonium sulfate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     dual
_audit_creation_date             2023-03-21
_audit_creation_method
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_audit_update_record
;
2024-02-27 deposited with the CCDC.	2024-04-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.149(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2928(2)
_cell_length_b                   11.3811(2)
_cell_length_c                   20.3088(4)
_cell_measurement_reflns_used    22898
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.0770
_cell_measurement_theta_min      4.3320
_cell_volume                     2135.55(7)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2687
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 0.9956
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -70.00  32.00   1.00    5.00    --  -41.26  57.00  30.00  102
  2  \w   -117.00 -30.00   1.00    5.00    --  -41.26 -77.00 -90.00   87
  3  \w      6.00  74.00   1.00    5.00    --   41.26 -77.00  90.00   68
  4  \w    -33.00  67.00   1.00    5.00    --   41.26 -38.00-150.00  100
  5  \w      8.00  87.00   1.00    5.00    --   41.26  77.00  30.00   79
  6  \w     12.00 113.00   1.00    5.00    --   41.26  57.00 150.00  101
  7  \w     76.00 158.00   1.00   20.00    --  105.17  59.00 114.62   82
  8  \w     76.00 158.00   1.00   20.00    --  105.17  55.00 -29.00   82
  9  \w     29.00 158.00   1.00   20.00    --  105.17  15.00 -60.00  129
 10  \w     76.00 158.00   1.00   20.00    --  105.17  53.00  53.47   82
 11  \w     73.00 158.00   1.00   20.00    --  105.17  66.00   5.25   85
 12  \w     56.00 112.00   1.00   20.00    --  105.17-125.00-180.00   56
 13  \w     32.00 132.00   1.00   20.00    --  105.17 -45.00  30.00  100
 14  \w     74.00 158.00   1.00   20.00    --  105.17  61.00  60.00   84
 15  \w     32.00 132.00   1.00   20.00    --  105.17 -45.00-180.00  100
 16  \w     78.00 158.00   1.00   20.00    --  105.17  45.00 -60.00   80
 17  \w     74.00 158.00   1.00   20.00    --  105.17  61.00  90.00   84
 18  \w     78.00 158.00   1.00   20.00    --  105.17  45.00  90.00   80
 19  \w     78.00 158.00   1.00   20.00    --  105.17  45.00  99.72   80
 20  \w     74.00 158.00   1.00   20.00    --  105.17  61.00-120.00   84
 21  \w     29.00 106.00   1.00   20.00    --  105.17 -94.00-180.00   77
 22  \w   -117.00 -30.00   1.00    5.00    --  -41.26 -77.00   0.00   87
 23  \w     34.00  82.00   1.00    5.00    --   41.26 -99.00 150.00   48
 24  \w      8.00  87.00   1.00    5.00    --   41.26  77.00-180.00   79
 25  \w     34.00  82.00   1.00    5.00    --   41.26 -99.00  30.00   48
 26  \w      8.00  87.00   1.00    5.00    --   41.26  77.00  90.00   79
 27  \w     15.00 115.00   1.00    5.00    --   41.26  38.00  30.00  100
 28  \w      8.00  87.00   1.00    5.00    --   41.26  77.00 -90.00   79
 29  \w     76.00 158.00   1.00   20.00    --  105.17  58.00 -19.34   82
 30  \w     77.00 158.00   1.00   20.00    --  105.17  54.00 142.59   81
 31  \w     74.00 158.00   1.00   20.00    --  105.17  61.00-150.00   84
 32  \w     56.00 112.00   1.00   20.00    --  105.17-125.00 -30.00   56
 33  \w     29.00 106.00   1.00   20.00    --  105.17 -94.00-150.00   77
 34  \w     32.00 132.00   1.00   20.00    --  105.17 -45.00 -60.00  100
 35  \w     74.00 158.00   1.00   20.00    --  105.17  61.00 -60.00   84
 36  \w     75.00 158.00   1.00   20.00    --  105.17  60.00-175.24   83
 37  \w     73.00 158.00   1.00   20.00    --  105.17  66.00 162.97   85
 38  \w     56.00 112.00   1.00   20.00    --  105.17-125.00 120.00   56
 39  \w     73.00 158.00   1.00   20.00    --  105.17  70.00  16.77   85
 40  \w     74.00 158.00   1.00   20.00    --  105.17  61.00 -90.00   84
 41  \w     74.00 158.00   1.00   20.00    --  105.17  65.00 146.00   84
 42  \w     29.00 106.00   1.00   20.00    --  105.17 -94.00   0.00   77
 43  \w   -121.00   3.00   1.00    5.00    --  -41.26 -19.00-180.00  124
 44  \w   -117.00 -30.00   1.00    5.00    --  -41.26 -77.00-120.00   87
 45  \w   -113.00 -12.00   1.00    5.00    --  -41.26 -57.00 -90.00  101
 46  \w     34.00  82.00   1.00    5.00    --   41.26 -99.00-180.00   48
 47  \w     12.00 113.00   1.00    5.00    --   41.26  57.00  90.00  101
 48  \w     34.00  82.00   1.00    5.00    --   41.26 -99.00  60.00   48
 49  \w      8.00  87.00   1.00    5.00    --   41.26  77.00   0.00   79
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1602580000
_diffrn_orient_matrix_UB_12      0.0182485000
_diffrn_orient_matrix_UB_13      0.0104581000
_diffrn_orient_matrix_UB_21      0.0448062000
_diffrn_orient_matrix_UB_22      0.0885957000
_diffrn_orient_matrix_UB_23      0.0557514000
_diffrn_orient_matrix_UB_31      -0.0102806000
_diffrn_orient_matrix_UB_32      0.1007765000
_diffrn_orient_matrix_UB_33      -0.0509811000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.048
_diffrn_reflns_Laue_measured_fraction_full 1.0000
_diffrn_reflns_Laue_measured_fraction_max 0.9956
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            6190
_diffrn_reflns_point_group_measured_fraction_full 1.0000
_diffrn_reflns_point_group_measured_fraction_max 0.9956
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         73.26
_diffrn_reflns_theta_min         4.38
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.887
_exptl_absorpt_correction_T_max  -0.010
_exptl_absorpt_correction_T_min  10000000.000
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_description       block
_exptl_crystal_F_000             861.924
_exptl_crystal_recrystallization_method
'Crystallization by slow evaporation of acetonitrile solution.'
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.3167
_refine_diff_density_min         -0.3708
_refine_diff_density_rms         0.0511
_refine_ls_d_res_high            0.8050
_refine_ls_d_res_low             10.0960
_refine_ls_goodness_of_fit_ref   1.0313
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    64
_refine_ls_number_parameters     237
_refine_ls_number_reflns         6190
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0313
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0324
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0411P)^2^+1.0882P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0814
_refine_ls_wR_factor_ref         0.0829
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              14
_reflns_limit_k_min              -14
_reflns_limit_l_max              24
_reflns_limit_l_min              -25
_reflns_number_gt                5563
_reflns_number_total             6190
_reflns_threshold_expression     I>=2u(I)
_twin_special_details
;
Component 2 rotated by 179.9967\% 
around [0.97 -0.00 -0.22] (reciprocal) or [1.00 0.00 0.00] (direct)
;
_cod_data_source_file            d4ce00210e2.cif
_cod_data_source_block           06
_cod_depositor_comments
'Adding full bibliography for 7248499--7248509.cif.'
_cod_database_code               7248503
_chemical_oxdiff_formula         'C16 H40 P2 S O4'
_chemical_oxdiff_usercomment     'TJ423 dehydrated at 120 C 1 h, cryst ACN'
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5116(10)
 0.4884(10)
2. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Others
 Sof(C00M)=Sof(C00P)=Sof(H00p)=Sof(H00q)=Sof(H00w)=Sof(H00x)=Sof(H00y)=1-FVAR(1)
 Sof(C00N)=Sof(C00O)=Sof(H00r)=Sof(H00s)=Sof(H00t)=Sof(H00u)=Sof(H00v)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C008(H00a,H00b), C009(H00z,H), C00A(H00,Ha), C00B(H1,Hb), C00C(H00c,H00d),
 C00D(H2,Hc), C00I(H00k,H00l), C00M(H00p,H00q), C00O(H00u,H00v)
4.b Idealised Me refined as rotating group:
 C00E(H3,Hd,He), C00F(H00e,H00f,H00g), C00G(H00h,H00i,H00j), C00H(H4,Hf,Hg),
 C00J(H5,Hh,Hi), C00K(H6,Hj,Hk), C00L(H00m,H00n,H00o), C00N(H00r,H00s,H00t),
 C00P(H00w,H00x,H00y)
;
_olex2_exptl_crystal_mounting_method loop
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.326
_oxdiff_exptl_absorpt_empirical_full_min 0.703
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2