One-step methylation of aromatic phosphorus heterocycles: synthesis and crystallographic characterization of a 1-methyl-phosphininium salt.
Fischer, Lukas; Wossidlo, Friedrich; Frost, Daniel; Coles, Nathan T.; Steinhauer, Simon; Riedel, Sebastian; Müller, Christian; Chemical communications (Cambridge, England) 57 (2021) 9522–9525; doi:10.1039/d1cc03892c

data_7128748
_publ_section_title
;
 One-step methylation of aromatic phosphorus heterocycles: synthesis and
 crystallographic characterization of a 1-methyl-phosphininium salt.
;
_journal_issue                   75
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              9522
_journal_page_last               9525
_journal_paper_doi               10.1039/d1cc03892c
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C17 H37 P Si4'
_chemical_formula_sum            'C17 H37 P Si4'
_chemical_formula_weight         384.79
_chemical_properties_physical    Air-sensitive
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-09-09
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-02-09 deposited with the CCDC.	2021-08-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0213(5)
_cell_length_b                   11.8221(5)
_cell_length_c                   18.3959(7)
_cell_measurement_reflns_used    9661
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      29.59
_cell_measurement_theta_min      2.76
_cell_volume                     2396.89(17)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_unetI/netI     0.0112
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            187764
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.612
_diffrn_reflns_theta_min         2.759
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.312
_exptl_absorpt_correction_T_max  0.9582
_exptl_absorpt_correction_T_min  0.8988
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0954 before and 0.0603 after correction.
The Ratio of minimum to maximum transmission is 0.9380.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.066
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: MeCN'
_exptl_crystal_size_max          0.309
_exptl_crystal_size_mid          0.282
_exptl_crystal_size_min          0.211
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.245
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3375
_refine_ls_number_restraints     116
_refine_ls_restrained_S_all      1.330
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0326
_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/[\s^2^(Fo^2^)+(0.0257P)^2^+0.9309P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0808
_refine_ls_wR_factor_ref         0.0849
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3075
_reflns_number_total             3375
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc03892c2.cif
_cod_data_source_block           ntc_tms4_2
_cod_depositor_comments
'Adding full bibliography for 7128747--7128748.cif.'
_cod_database_code               7128748
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 Si1-C1 \\sim Si1-C6 \\sim Si1-C8 \\sim Si1-C7
 with sigma of 0.02
 Si2-C2 \\sim Si2-C9 \\sim Si2-C10 \\sim Si2-C11
 with sigma of 0.02
 C2-C9 \\sim C2-C10 \\sim C2-C11 \\sim C9-C10 \\sim C9-C11 \\sim C10-C11
 with sigma of 0.04
 C1-C6 \\sim C1-C8 \\sim C1-C7 \\sim C6-C8 \\sim C6-C7 \\sim C8-C7
 with sigma of 0.04
 Si3-C4 \\sim Si3-C13 \\sim Si3-C14 \\sim Si3-C12
 with sigma of 0.02
 C4-C13 \\sim C4-C14 \\sim C4-C12 \\sim C13-C14 \\sim C13-C12 \\sim C14-C12
 with sigma of 0.04
 Si4-C5 \\sim Si4-C15 \\sim Si4-C16 \\sim Si4-C17
 with sigma of 0.02
 C5-C15 \\sim C5-C16 \\sim C5-C17 \\sim C16-C17 \\sim C16-C15 \\sim C17-C15
 with sigma of 0.04
3. Rigid body (RIGU) restrains
 P1, C1, C2, C3, C4, C5
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Fixed Sof: P1(0.5) Si1(0.5) Si2(0.5) Si3(0.5) Si4(0.5) C1(0.5) C2(0.5)
 C3(0.5) H3(0.5) C4(0.5) C5(0.5) C6(0.5) H6A(0.5) H6B(0.5) H6C(0.5) C7(0.5)
 H7A(0.5) H7B(0.5) H7C(0.5) C8(0.5) H8A(0.5) H8B(0.5) H8C(0.5) C9(0.5) H9A(0.5)
 H9B(0.5) H9C(0.5) C10(0.5) H10A(0.5) H10B(0.5) H10C(0.5) C11(0.5) H11A(0.5)
 H11B(0.5) H11C(0.5) C12(0.5) H12A(0.5) H12B(0.5) H12C(0.5) C13(0.5) H13A(0.5)
 H13B(0.5) H13C(0.5) C14(0.5) H14A(0.5) H14B(0.5) H14C(0.5) C15(0.5) H15A(0.5)
 H15B(0.5) H15C(0.5) C16(0.5) H16A(0.5) H16B(0.5) H16C(0.5) C17(0.5) H17A(0.5)
 H17B(0.5) H17C(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C3(H3)
5.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,
 H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C),
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,
 H17C)
;
_shelx_res_checksum              76918
_olex2_submission_original_sample_id NTC-TMS4_2
_olex2_submission_special_instructions 'No special instructions were received'