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_7248499
_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         'C16 H36 P, H O4 S'
_chemical_formula_sum            'C16 H37 O4 P S'
_chemical_formula_weight         356.510
_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             2024-04-12
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-04-12 deposited with the CCDC.	2024-04-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.595(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.7521(2)
_cell_length_b                   22.0007(3)
_cell_length_c                   13.9604(2)
_cell_measurement_reflns_used    21048
_cell_measurement_temperature    100
_cell_measurement_theta_max      74.8870
_cell_measurement_theta_min      3.8210
_cell_volume                     4068.31(11)
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100
_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 0.9924
_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    -66.00  34.00   1.00    3.00    --  -41.26  38.00-120.00  100
  2  \w     58.00  85.00   1.00    3.00    --   41.26  77.00 -90.00   27
  3  \w      8.00  47.00   1.00    3.00    --   41.26  77.00  60.00   39
  4  \w      9.00  86.00   1.00    3.00    --   41.26  77.00-120.00   77
  5  \w     34.00  81.00   1.00    3.00    --   41.26 -99.00 -60.00   47
  6  \w     37.00 130.00   1.00   12.00    --  109.50 -45.00  90.00   93
  7  \w     85.00 112.00   1.00   12.00    --  109.50  45.00  30.00   27
  8  \w     91.00 128.00   1.00   12.00    --  109.50 178.00 -30.00   37
  9  \w     38.00 118.00   1.00   12.00    --  109.50 -45.00-120.00   80
 10  \w     44.00  81.00   1.00   12.00    --  109.50-111.00-180.00   37
 11  \w     80.00 157.00   1.00   12.00    --  109.50  61.00  60.00   77
 12  \w     48.00 157.00   1.00   12.00    --  109.50   0.00-150.00  109
 13  \w     94.00 152.00   1.00   22.00    --  109.50  45.00-150.00   58
 14  \w    122.00 155.00   1.00   22.00    --  109.50  50.00  44.00   33
 15  \w     63.00  89.00   1.00   22.00    --  109.50 -94.00-150.00   26
 16  \w     79.00 105.00   1.00   22.00    --  109.50 -94.00-180.00   26
 17  \w     84.00 110.00   1.00   22.00    --  109.50  45.00 120.00   26
 18  \w     61.00 103.00   1.00   22.00    --  109.50-111.00 -60.00   42
 19  \w    105.00 145.00   1.00   22.00    --  109.50  45.00-180.00   40
 20  \w    125.00 151.00   1.00   22.00    --  109.50  30.00 -90.00   26
 21  \w     92.00 123.00   1.00   22.00    --  109.50 178.00 120.00   31
 22  \w     32.00  74.00   1.00   22.00    --  109.50 -94.00 -30.00   42
 23  \w    109.00 135.00   1.00   22.00    --  109.50 178.00 -90.00   26
 24  \w     81.00 126.00   1.00   22.00    --  109.50  15.00-180.00   45
 25  \w     96.00 145.00   1.00   22.00    --  109.50  30.00   0.00   49
 26  \w   -114.00 -12.00   1.00    4.00    --  -41.51 -57.00  90.00  102
 27  \w    -75.00  34.00   1.00    4.00    --  -41.51  77.00   0.00  109
 28  \w      9.00  87.00   1.00    4.00    --   41.51  77.00 120.00   78
 29  \w      6.00  75.00   1.00    4.00    --   41.51 -77.00  60.00   69
 30  \w      9.00  87.00   1.00    4.00    --   41.51  77.00 -30.00   78
 31  \w     78.00 137.00   1.00   22.00    --  109.50  30.00 -60.00   59
 32  \w     89.00 146.00   1.00   22.00    --  109.50 178.00-180.00   57
 33  \w    112.00 137.00   1.00   22.00    --  109.50 -50.00-101.00   25
 34  \w     38.00  71.00   1.00   22.00    --  109.50 -61.00  30.00   33
 35  \w    102.00 128.00   1.00   22.00    --  109.50 -61.00  30.00   26
 36  \w     93.00 133.00   1.00   22.00    --  109.50  37.00 171.74   40
 37  \w     97.00 123.00   1.00   22.00    --  109.50  30.00 -30.00   26
 38  \w     65.00 107.00   1.00   22.00    --  109.50-111.00 -90.00   42
 39  \w     72.00 118.00   1.00   22.00    --  109.50 -61.00  60.00   46
 40  \w    107.00 140.00   1.00   22.00    --  109.50  59.00 175.20   33
 41  \w     58.00  92.00   1.00   22.00    --  109.50 -45.00  30.00   34
 42  \w    112.00 137.00   1.00   22.00    --  109.50 -45.00  30.00   25
 43  \w     20.00  45.00   1.00   22.00    --  109.50   3.00-129.40   25
 44  \w     51.00  77.00   1.00   22.00    --  109.50   3.00-129.40   26
 45  \w     76.00 102.00   1.00   22.00    --  109.50 -94.00 -30.00   26
 46  \w     33.00  59.00   1.00   22.00    --  109.50 -94.00   0.00   26
 47  \w     67.00  94.00   1.00   22.00    --  109.50  21.00 -54.42   27
 48  \w    104.00 130.00   1.00   22.00    --  109.50 -30.00 -60.00   26
 49  \w     59.00  85.00   1.00   22.00    --  109.50 -15.00-180.00   26
 50  \w    125.00 152.00   1.00   22.00    --  109.50 -15.00-180.00   27
 51  \w    113.00 141.00   1.00   22.00    --  109.50  45.00   0.00   28
;
_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      -0.0615310000
_diffrn_orient_matrix_UB_12      0.0377091000
_diffrn_orient_matrix_UB_13      -0.0886675000
_diffrn_orient_matrix_UB_21      0.0716303000
_diffrn_orient_matrix_UB_22      -0.0202116000
_diffrn_orient_matrix_UB_23      -0.0619961000
_diffrn_orient_matrix_UB_31      -0.0678673000
_diffrn_orient_matrix_UB_32      -0.0554304000
_diffrn_orient_matrix_UB_33      -0.0376895000
_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  0.0568
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 1.0000
_diffrn_reflns_Laue_measured_fraction_max 0.9924
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            43613
_diffrn_reflns_point_group_measured_fraction_full 1.0000
_diffrn_reflns_point_group_measured_fraction_max 0.9924
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         75.26
_diffrn_reflns_theta_min         3.85
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.267
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.405
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
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    1.164
_exptl_crystal_description       trapezoid
_exptl_crystal_F_000             1577.369
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_refine_diff_density_max         1.3243
_refine_diff_density_min         -0.6992
_refine_diff_density_rms         0.0708
_refine_ls_d_res_high            0.7971
_refine_ls_d_res_low             11.4733
_refine_ls_goodness_of_fit_ref   1.0448
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    175
_refine_ls_number_parameters     564
_refine_ls_number_reflns         8356
_refine_ls_number_restraints     264
_refine_ls_restrained_S_all      1.0276
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0630
_refine_ls_shift/su_max          -0.0012
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0622P)^2^+4.9978P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1532
_refine_ls_wR_factor_ref         0.1594
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -17
_reflns_limit_k_max              27
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              -9
_reflns_number_gt                7228
_reflns_number_total             8356
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4ce00210e2.cif
_cod_data_source_block           20230420_TJ417air01
_cod_depositor_comments
'Adding full bibliography for 7248499--7248509.cif.'
_cod_database_code               7248499
_chemical_oxdiff_formula         'C16 H37 O4 P S'
_chemical_oxdiff_usercomment
'TJ417 stored without Krytox in the air for 3 months TBPHS'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C21-C00L \\sim C21-C20 \\sim C00V-C00L \\sim C017-C00V
 with sigma of 0.02
 P1-C5 \\sim P1-C10 \\sim P004-C00U \\sim P004-C00T \\sim P004-C00O \\sim
P004-C00N
 with sigma of 0.01
 C6-C5 \\sim C7-C6 \\sim C9-C7 \\sim C13-C12 \\sim C12-C11 \\sim C11-C10
 with sigma of 0.02
 C4-C00D \\sim C00W-C00D \\sim C4-C3 \\sim C014-C00W \\sim C015-C014 \\sim
C3-C1 \\sim C00L-C00I \\sim C21-
 C00L \\sim C00V-C00L \\sim C017-C00V \\sim C21-C20 \\sim C010-C00H \\sim
C8-C00H \\sim C8-C2 \\sim C018-
 C010
 with sigma of 0.01
 C012-C00U \\sim C013-C012 \\sim C013-C00Z \\sim C6-C5 \\sim C7-C6 \\sim C9-C7
\\sim C11-C10 \\sim C00T-
 C00Q \\sim C12-C11 \\sim C00Y-C00Q \\sim C13-C12 \\sim C016-C00Y
 with sigma of 0.01
 O006-H006 \\sim O008-H008
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C9 \\sim C00Z \\sim C7 \\sim C013 \\sim C6 \\sim C012 \\sim C5 \\sim C00U \\sim
C10 \\sim C00T \\sim C11 \\sim C00Q \\sim C12 \\sim C00Y \\sim C13 \\sim C016:
within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04 within 1.7A
P1 \\sim P004: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 1.7A
C21 \\sim C00V: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08 within 1.7A
Uanis(C21) \\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.1
Uanis(C012) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.1
Uanis(C5) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.1
4. Rigid body (RIGU) restrains
 C00L, C21
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(Hg)=Sof(Hh)=Sof(C2)=Sof(H2a)=Sof(H2b)=Sof(H2c)=Sof(C8)=Sof(H8a)=Sof(H8b)=
 1-FVAR(1)
 Sof(H5)=Sof(Hf)=Sof(C010)=Sof(H01k)=Sof(H01l)=Sof(C018)=Sof(H01u)=Sof(H01v)=
 Sof(H01w)=FVAR(1)
 Sof(Ha)=Sof(Hb)=Sof(C3)=Sof(H3a)=Sof(H3b)=Sof(C1)=Sof(H1a)=Sof(H1b)=Sof(H1c)=
 Sof(C4)=Sof(H4a)=Sof(H4b)=1-FVAR(2)
 Sof(H1)=Sof(H)=Sof(C00W)=Sof(H11)=Sof(Hq)=Sof(C014)=Sof(H01m)=Sof(H01n)=
 Sof(C015)=Sof(H01o)=Sof(H01p)=Sof(H01q)=FVAR(2)
 Sof(Hl)=Sof(Hm)=Sof(C20)=Sof(H20a)=Sof(H20b)=Sof(H20c)=Sof(C21)=Sof(H21a)=
 Sof(H21b)=1-FVAR(3)
 Sof(H8)=Sof(Hk)=Sof(C00V)=Sof(H10)=Sof(Hp)=Sof(C017)=Sof(H01r)=Sof(H01s)=
 Sof(H01t)=FVAR(3)
 Sof(H00g)=Sof(H00h)=Sof(H00k)=Sof(H00l)=Sof(C11)=Sof(H11a)=Sof(H11b)=Sof(C10)=
 Sof(H10a)=Sof(H10b)=Sof(C12)=Sof(H12a)=Sof(H12b)=Sof(P1)=Sof(C5)=Sof(H5a)=
 Sof(H5b)=Sof(C6)=Sof(H6a)=Sof(H6b)=Sof(C9)=Sof(H9a)=Sof(H9b)=Sof(H9c)=Sof(C7)=
 Sof(H7a)=Sof(H7b)=Sof(C13)=Sof(H13a)=Sof(H13b)=Sof(H13c)=1-FVAR(4)
 Sof(P004)=Sof(H00e)=Sof(H00f)=Sof(H00i)=Sof(H00j)=Sof(C00Q)=Sof(H00m)=
 Sof(H00n)=Sof(C00T)=Sof(H00t)=Sof(H00u)=Sof(C00U)=Sof(H00v)=Sof(H00w)=
 Sof(C00Y)=Sof(H00z)=Sof(Hr)=Sof(C00Z)=Sof(H00)=Sof(Hs)=Sof(Ht)=Sof(C012)=
 Sof(H01d)=Sof(H01e)=Sof(C013)=Sof(H01f)=Sof(H01g)=Sof(C016)=Sof(H01h)=
 Sof(H01i)=Sof(H01j)=FVAR(4)
 Fixed Uiso: H008(0.077896) H006(0.073899)
6.a Secondary CH2 refined with riding coordinates:
 C00D(H1,H), C00D(Ha,Hb), C00E(H2,Hc), C00F(H3,Hd), C00G(H4,He), C00H(H5,Hf),
 C00H(Hg,Hh), C00I(H6,Hi), C00J(H00a,H00b), C00K(H7,Hj), C00L(H8,Hk), C00L(Hl,
 Hm), C00M(H00c,H00d), C00N(H00e,H00f), C00N(H00g,H00h), C00O(H00i,H00j),
 C00O(H00k,H00l), C00Q(H00m,H00n), C00S(H00r,H00s), C00T(H00t,H00u), C00U(H00v,
 H00w), C00V(H10,Hp), C00W(H11,Hq), C00X(H00x,H00y), C00Y(H00z,Hr), C010(H01k,
 H01l), C012(H01d,H01e), C013(H01f,H01g), C014(H01m,H01n), C3(H3a,H3b), C4(H4a,
 H4b), C8(H8a,H8b), C11(H11a,H11b), C10(H10a,H10b), C21(H21a,H21b), C12(H12a,
 H12b), C5(H5a,H5b), C6(H6a,H6b), C7(H7a,H7b)
6.b Idealised Me refined as rotating group:
 C00P(H9,Hn,Ho), C00R(H00o,H00p,H00q), C00Z(H00,Hs,Ht), C011(H01a,H01b,H01c),
 C015(H01o,H01p,H01q), C016(H01h,H01i,H01j), C017(H01r,H01s,H01t), C018(H01u,
 H01v,H01w), C1(H1a,H1b,H1c), C2(H2a,H2b,H2c), C20(H20a,H20b,H20c), C9(H9a,H9b,
 H9c), C13(H13a,H13b,H13c)
;
_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 2.293
_oxdiff_exptl_absorpt_empirical_full_min 0.655