All-carbon phosphoranes <i>via</i> difluorocarbene trapping.
Smirnov, Vladimir O.; Volodin, Alexander D.; Korlyukov, Alexander A.; Dilman, Alexander D.; Chemical communications (Cambridge, England) 57 (2021) 4823–4826; doi:10.1039/d1cc01075a

data_7128144
_publ_section_title
;
 All-carbon phosphoranes <i>via</i> difluorocarbene trapping.
;
_journal_issue                   39
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              4823
_journal_page_last               4826
_journal_paper_doi               10.1039/d1cc01075a
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         '1(C20 H15 F4 O P)'
_chemical_formula_sum            'C20 H15 F4 O P'
_chemical_formula_weight         378.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-02-05
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-02-08 deposited with the CCDC.	2021-04-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.9180(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.0201(6)
_cell_length_b                   9.3245(4)
_cell_length_c                   25.3352(11)
_cell_measurement_reflns_used    9910
_cell_measurement_temperature    120
_cell_measurement_theta_max      25.476
_cell_measurement_theta_min      2.337
_cell_volume                     3428.7(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/6 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      120
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker SMART CCD 1K area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0741
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            74625
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.580
_diffrn_reflns_theta_min         1.664
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7001
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0596 before and 0.0540 after correction. The Ratio of minimum to maximum transmission is 0.9383. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_description       prism
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.396
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     556
_refine_ls_number_reflns         10542
_refine_ls_number_restraints     37
_refine_ls_restrained_S_all      1.100
_refine_ls_R_factor_all          0.0950
_refine_ls_R_factor_gt           0.0552
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0241P)^2^+3.8533P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1084
_refine_ls_wR_factor_ref         0.1216
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7197
_reflns_number_total             10542
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc01075a2.cif
_cod_data_source_block           sv752a
_cod_depositor_comments
'Adding full bibliography for 7128144--7128146.cif.'
_cod_database_code               7128144
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.954
_shelx_estimated_absorpt_t_min   0.929
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O1B-C1B \\sim F1B-C1B \\sim F2B-C1B
 with sigma of 0.02
 P1A-C14A \\sim P1A-C8B
 with sigma of 0.02
 F4B-C20B \\sim F3B-C20B \\sim F2A-C1A \\sim F1A-C1A
 with sigma of 0.02
 P1A-C8C \\sim P1A-C3A \\sim P1A-C3B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C6B) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C4B) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C1C) \\sim Ueq, Uanis(O1B) \\sim Ueq: with sigma of 0.015 and sigma for
terminal atoms of 0.03
Uanis(C20A) = Uanis(C1B)
Uanis(F1B) = Uanis(F4A)
Uanis(F3A) = Uanis(F2B)
Uanis(C14A) = Uanis(C8B)
Uanis(C19A) = Uanis(C13B)
Uanis(C18A) = Uanis(C12B)
Uanis(C17A) = Uanis(C11B)
Uanis(C16A) = Uanis(C10B)
Uanis(C15A) = Uanis(C9B)
Uanis(F3B) = Uanis(F2A)
Uanis(F4B) = Uanis(F1A)
Uanis(C20B) = Uanis(C1A)
Uanis(F2C) = Uanis(F1A) = Uanis(F4B)
Uanis(F3B) = Uanis(F2A) = Uanis(F1C)
Uanis(C3C) = Uanis(C8A)
Uanis(C13A) = Uanis(C4C)
Uanis(C12A) = Uanis(C5C)
Uanis(C11A) = Uanis(C6C)
Uanis(C7C) = Uanis(C10A)
Uanis(C2C) = Uanis(C9A)
Uanis(C11C) = Uanis(C6A)
Uanis(C10C) = Uanis(C7A)
Uanis(C2A) = Uanis(C9C)
Uanis(C4A) = Uanis(C13C)
Uanis(C5A) = Uanis(C12C)
Uanis(C8C) = Uanis(C3A)
Uanis(C5B) = Uanis(C5A)
Uanis(C3B) = Uanis(C3A)
4. Others
 Fixed Sof: F1A(0.7) F1B(0.18) F1C(0.12) F2A(0.7) F2B(0.18) F2C(0.12)
 F3A(0.82) F3B(0.18) F4A(0.82) F4B(0.18) O1A(0.7) O1B(0.18) O1C(0.12) C1A(0.7)
 C1B(0.18) C1C(0.12) C3A(0.7) C2A(0.7) C7A(0.7) H7A(0.7) C6A(0.7) H6A(0.7)
 C5A(0.7) H5A(0.7) C4A(0.7) H4A(0.7) C3B(0.18) C4B(0.18) H4B(0.18) C5B(0.18)
 H5B(0.18) C6B(0.18) H6B(0.18) C7B(0.18) H7B(0.18) C2B(0.18) C4C(0.12)
 H4C(0.12) C5C(0.12) H5C(0.12) C6C(0.12) H6C(0.12) C7C(0.12) H7C(0.12)
 C2C(0.12) C3C(0.12) C8A(0.88) C8B(0.18) C13B(0.18) H13B(0.18) C12B(0.18)
 H12B(0.18) C11B(0.18) H11B(0.18) C10B(0.18) H10B(0.18) C9B(0.18) H9B(0.18)
 C9A(0.88) H9A(0.88) C10A(0.88) H10A(0.88) C10C(0.12) H10C(0.12) C11C(0.12)
 H11C(0.12) C12C(0.12) H12C(0.12) C13C(0.12) H13C(0.12) C8C(0.12) C9C(0.12)
 H9C(0.12) C11A(0.88) H11A(0.88) C12A(0.88) H12A(0.88) C13A(0.88) H13A(0.88)
 C14A(0.82) C15A(0.82) H15A(0.82) C16A(0.82) H16A(0.82) C17A(0.82) H17A(0.82)
 C18A(0.82) H18A(0.82) C19A(0.82) H19A(0.82) C20A(0.82) H20A(0.82) C20B(0.18)
 H20B(0.18)
5.a Ternary CH refined with riding coordinates:
 C20(H20), C20A(H20A), C20B(H20B)
5.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C7A(H7A), C6A(H6A),
  C5A(H5A), C4A(H4A), C4B(H4B), C5B(H5B), C6B(H6B), C7B(H7B), C4C(H4C),
 C5C(H5C), C6C(H6C), C7C(H7C), C13B(H13B), C12B(H12B), C11B(H11B), C10B(H10B),
 C9B(H9B), C9A(H9A), C10A(H10A), C10C(H10C), C11C(H11C), C12C(H12C), C13C(H13C),
  C9C(H9C), C11A(H11A), C12A(H12A), C13A(H13A), C15A(H15A), C16A(H16A),
 C17A(H17A), C18A(H18A), C19A(H19A)
5.c Fitted hexagon refined as free rotating group:
 C3A(C2A,C7A,C6A,C5A,C4A), C3B(C4B,C5B,C6B,C7B,C2B), C4C(C5C,C6C,C7C,C2C,C3C),
 C8B(C13B,C12B,C11B,C10B,C9B), C10C(C11C,C12C,C13C,C8C,C9C)
;
_shelx_res_checksum              8395
_olex2_submission_special_instructions 'No special instructions were received'