Direct functionalization of white phosphorus with anionic dicarbenes and mesoionic carbenes: Facile access to 1,2,3-triphosphol-2-ides
Ghadwal, Rajendra S.; Rottschäfer, Dennis; Blomeyer, Sebastian; Neumann, Beate; Stammler, Georg; Chemical Science  (2019) –; doi:10.1039/C9SC04441H

data_1552448
_publ_section_title
;
 Direct functionalization of white phosphorus with anionic dicarbenes and
 mesoionic carbenes: Facile access to 1,2,3-triphosphol-2-ides
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC04441H
_journal_year                    2019
_chemical_formula_moiety         'C33 H39 N2 P3'
_chemical_formula_sum            'C33 H39 N2 P3'
_chemical_formula_weight         556.57
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-11-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-10 deposited with the CCDC.    2019-10-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.414(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5947(8)
_cell_length_b                   16.2615(8)
_cell_length_c                   17.8991(13)
_cell_measurement_reflns_used    2925
_cell_measurement_temperature    99.9(3)
_cell_measurement_theta_max      76.4040
_cell_measurement_theta_min      5.0190
_cell_volume                     3058.0(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3114
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_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    -88.00 -15.00   1.00   55.50    --  -38.50 -57.00 -60.00   73
  2  \w   -115.00 -26.00   1.00   55.50    --  -38.50 -19.00   0.00   89
  3  \w    -63.00  29.00   1.00   55.50    --  -38.50  57.00 120.00   92
  4  \w     19.00  54.00   1.00   55.50    --   43.20  77.00 -60.00   35
  5  \w     57.00 127.00   1.00   55.50    --   43.20 178.00 -60.00   70
  6  \w     88.00 115.00   1.00   55.50    --   43.20  77.00 -60.00   27
  7  \w    102.00 127.00   1.00   55.50    --   43.20 178.00-180.00   25
  8  \w     69.00 117.00   1.00  111.00    --  111.00-125.00 150.00   48
  9  \w     42.00  67.00   1.00  111.00    --  111.00-125.00 -60.00   25
 10  \w     56.00 105.00   1.00  111.00    --  111.00 -77.00   0.00   49
 11  \w     41.00 117.00   1.00  111.00    --  111.00-125.00-150.00   76
 12  \w     38.00 118.00   1.00  111.00    --  111.00 -30.00 -60.00   80
 13  \w     90.00 152.00   1.00  111.00    --  111.00  30.00-120.00   62
 14  \w     82.00 172.00   1.00  111.00    --  111.00  77.00 -90.00   90
 15  \w     45.00 135.00   1.00  111.00    --  111.00 -61.00-150.00   90
 16  \w     61.00 117.00   1.00  111.00    --  111.00-125.00  30.00   56
 17  \w     45.00 120.00   1.00  111.00    --  111.00 -45.00  30.00   75
 18  \w    129.00 155.00   1.00  111.00    --  111.00  30.00-150.00   26
 19  \w    102.00 178.00   1.00  111.00    --  111.00  45.00 -30.00   76
 20  \w     90.00 117.00   1.00  111.00    --  111.00-125.00 -30.00   27
 21  \w     95.00 127.00   1.00  111.00    --  111.00 125.00-150.00   32
 22  \w     43.00 106.00   1.00  111.00    --  111.00 -77.00-180.00   63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0050853000
_diffrn_orient_matrix_UB_12      0.0705067000
_diffrn_orient_matrix_UB_13      -0.0578821000
_diffrn_orient_matrix_UB_21      0.1463634000
_diffrn_orient_matrix_UB_22      0.0054573000
_diffrn_orient_matrix_UB_23      0.0123777000
_diffrn_orient_matrix_UB_31      0.0070472000
_diffrn_orient_matrix_UB_32      -0.0630012000
_diffrn_orient_matrix_UB_33      -0.0635574000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0747
_diffrn_reflns_av_sigmaI/netI    0.0869
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            17147
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.546
_diffrn_reflns_theta_min         4.983
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.959
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.755
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.209
_exptl_crystal_description       needle
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.174
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         5324
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0437
_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^)+(0.0735P)^2^+0.0459P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1184
_refine_ls_wR_factor_ref         0.1298
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3981
_reflns_number_total             5324
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc04441h2.cif
_cod_data_source_block           compound4a
_cod_database_code               1552448
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C33 H39 N2 P3'
_shelx_estimated_absorpt_t_max   0.962
_shelx_estimated_absorpt_t_min   0.727
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5933(14)
 0.4067(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C9(H9), C12(H12)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C16(H16), C17(H17), C18(H18)
3.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C13(H13A,H13B,H13C), C14(H14A,H14B,
 H14C)
;
_shelx_res_checksum              20294
_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 1.345
_oxdiff_exptl_absorpt_empirical_full_min 0.833
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
_twin_special_details
;
Component 2 rotated by 179.8773\% 
 around [0.98 0.00 -0.21] (reciprocal) or [1.00 -0.00 0.00] (direct)
;