A 2,2′-diphosphinotolane as a versatile precursor for the synthesis of P-ylidic mesoionic carbenes via reversible C‒P bond formation
Wagner, Hannah K.; Wadepohl, Hubert; Ballmann, Joachim; Chemical Science 12 (2021) 3693–3701; doi:10.1039/D0SC06128J

data_1560226
_publ_section_title
;
 A 2,2&#x2032;-diphosphinotolane as a versatile precursor for the
 synthesis of P-ylidic mesoionic carbenes via reversible C--P bond
 formation
;
_journal_issue                   10
_journal_name_full               'Chemical Science'
_journal_page_first              3693
_journal_page_last               3701
_journal_paper_doi               10.1039/D0SC06128J
_journal_volume                  12
_journal_year                    2021
_chemical_formula_moiety         'C31 H39 N O3 P2 W, C2 H3 N'
_chemical_formula_sum            'C33 H42 N2 O3 P2 W'
_chemical_formula_weight         760.47
_chemical_properties_physical    'air-sensitive, moisture-sensitive'
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   difmap
_audit_block_code                ba_hw8
_audit_creation_date             2020-04-28
_audit_creation_method
;
encif (version 1.112)

encifer (version_id = 270009.64)

Olex2 1.3
(compiled 2020.01.31 svn.r88ba2a3 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-10-08 deposited with the CCDC.	2021-01-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.989(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.771(5)
_cell_length_b                   18.020(9)
_cell_length_c                   16.983(8)
_cell_measurement_reflns_used    7613
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.17
_cell_measurement_theta_min      2.22
_cell_volume                     3264(3)
_computing_cell_refinement
;
SAINT (see _computing_data_reduction).
Standard uncertainties of the cell constants include systematic error
contributions from Monte Carlo simulations.
;
_computing_data_collection       'SMART-5.631 (Bruker AXS, 2003)'
_computing_data_reduction
'SAINT V8.38A (Bruker AXS, 1997-2013),SADABS-2016_2 (Sheldrick and Bruker AXS, 1997-2014)'
_computing_publication_material
'encif (Wadepohl, 2009-19); encifer (Allen et al., 2004)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'DIRDIF (Beurskens et al., 1999-2008)'
_diffrn_ambient_environment      'perfluoro polyether oil / N~2~'
_diffrn_ambient_temperature      100(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.19
_diffrn_detector_type            CCD-PXL-KAF2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker AXS Smart 1000'
_diffrn_measurement_method       '\f- and \w-scans'
_diffrn_measurement_specimen_support 'polyimid foil'
_diffrn_radiation_collimation    'monocapillary collimator'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~2,3~
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            83195
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.475
_diffrn_reflns_theta_min         2.114
_diffrn_source                   'sealed X-Ray tube (Mo)'
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_type              'fine focus tube'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.672
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.6717
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements (Blessing 1995)
SADABS (see _computing_data_reduction)
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_description       block
_exptl_crystal_F_000             1528
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.251
_refine_diff_density_min         -0.593
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     400
_refine_ls_number_reflns         11202
_refine_ls_number_restraints     31
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0206
_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^)+(0.0171P)^2^+3.1435P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0439
_refine_ls_wR_factor_ref         0.0467
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9786
_reflns_number_total             11202
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc06128j2.cif
_cod_data_source_block           ba_hw8
_cod_depositor_comments
'Adding full bibliography for 1560218--1560233.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1560226
_audit_block_refno               3252
_audit_block_usercomment         HW101
_shelx_estimated_absorpt_t_max   0.710
_shelx_estimated_absorpt_t_min   0.710
_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, All C(H,H,H,H,H,H) groups
2. Restrained distances
 C21A-C22A \\sim C21B-C22B \\sim C21A-C23 \\sim C21B-C23
 with sigma of 0.02
 C22A-C23 \\sim C22B-C23
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9
\\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17
\\sim C18 \\sim C19 \\sim C20 \\sim C23 \\sim C24 \\sim C25 \\sim C26 \\sim C27
\\sim C28 \\sim C29 \\sim C30 \\sim C31 \\sim C21A \\sim C22A \\sim C21B \\sim
C22B \\sim C51 \\sim C52: within 1A with sigma of 0.01 and sigma for terminal
atoms of 0.01 within 1A
4. Rigid body (RIGU) restrains
 C23, C21A, C22A, C21B, C22B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(H23D)=Sof(H23F)=Sof(H23E)=Sof(C21B)=Sof(H21B)=Sof(C22B)=Sof(H22D)=
 Sof(H22E)=Sof(H22F)=1-FVAR(1)
 Sof(H23A)=Sof(H23B)=Sof(H23C)=Sof(C21A)=Sof(H21A)=Sof(C22A)=Sof(H22A)=
 Sof(H22B)=Sof(H22C)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C15(H15), C18(H18), C24(H24), C21A(H21A), C21B(H21B)
6.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14)
6.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C23(H23A,H23B,H23C), C23(H23D,H23F,H23E), C25(H25A,H25B,H25C), C26(H26A,
 H26B,H26C), C31(H31A,H31B,H31C), C22A(H22A,H22B,H22C), C22B(H22D,H22E,H22F),
 C52(H52A,H52B,H52C)
;
_shelx_res_checksum              67631