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_7128747
_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         'Al F20 O4 Te4, C18 H40 P Si4'
_chemical_formula_sum            'C18 H40 Al F20 O4 P Si4 Te4'
_chemical_formula_weight         1381.21
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-01-29
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-02-09 deposited with the CCDC.	2021-08-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.5900(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0027(4)
_cell_length_b                   16.9978(5)
_cell_length_c                   21.5539(7)
_cell_measurement_reflns_used    9579
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      30.51
_cell_measurement_theta_min      2.27
_cell_volume                     4397.2(2)
_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 0.996
_diffrn_measured_fraction_theta_max 0.998
_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  0.0296
_diffrn_reflns_av_unetI/netI     0.0122
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            189889
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.540
_diffrn_reflns_theta_min         2.077
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.903
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.3836
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1023 before and 0.0497 after correction.
The Ratio of minimum to maximum transmission is 0.3836.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.086
_exptl_crystal_description       Block
_exptl_crystal_F_000             2608
_exptl_crystal_size_max          0.458
_exptl_crystal_size_mid          0.328
_exptl_crystal_size_min          0.246
_refine_diff_density_max         0.567
_refine_diff_density_min         -0.540
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Flack x determined using 6489 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.059(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     483
_refine_ls_number_reflns         13410
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0180
_refine_ls_R_factor_gt           0.0174
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0198P)^2^+6.6692P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0416
_refine_ls_wR_factor_ref         0.0421
_reflns_Friedel_coverage         0.997
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                13205
_reflns_number_total             13410
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc03892c2.cif
_cod_data_source_block           lf104
_cod_depositor_comments
'Adding full bibliography for 7128747--7128748.cif.'
_cod_database_code               7128747
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.535
_shelx_estimated_absorpt_t_min   0.350
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3)
2.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), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              76445
_olex2_submission_special_instructions 'No special instructions were received'