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_1552453
_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         'C34 H41 N2 P3'
_chemical_formula_sum            'C34 H41 N2 P3'
_chemical_formula_weight         570.60
_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             2019-04-08
_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                 102.358(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8550(3)
_cell_length_b                   15.5962(3)
_cell_length_c                   19.1059(4)
_cell_measurement_reflns_used    27571
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      32.6240
_cell_measurement_theta_min      3.4780
_cell_volume                     3159.62(13)
_computing_cell_refinement       'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.47a (Rigaku OD, 2019)'
_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      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3114
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.971
_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    -38.00  54.00   1.00    5.50    --  -17.14  38.00 120.00   92
  2  \w    -76.00 -27.00   1.00    5.50    --  -17.14 132.00 101.29   49
  3  \w    -13.00  88.00   1.00    5.50    --   17.14  77.00-150.00  101
  4  \w     -8.00  86.00   1.00    5.50    --   17.14  57.00   0.00   94
  5  \w    -54.00  38.00   1.00    5.50    --   17.14 -38.00 -60.00   92
  6  \w     -8.00  86.00   1.00    5.50    --   17.14  57.00 120.00   94
  7  \w    -54.00  47.00   1.00    5.50    --   17.14 -77.00-150.00  101
  8  \w    -32.00  53.00   1.00    5.50    --   17.14 -90.00 -83.29   85
  9  \w    -11.00  62.00   1.00    5.50    --   17.14-110.00  65.63   73
 10  \w    -91.00 -39.00   1.00    5.50    --  -17.14 154.00-144.14   52
 11  \w    -91.00 -39.00   1.00    5.50    --  -17.14 154.00 135.98   52
 12  \w    -84.00 -34.00   1.00    5.50    --  -17.14 146.00 -80.12   50
 13  \w     35.00 101.00   1.00    5.50    --   17.14 178.00 120.00   66
 14  \w    -13.00  88.00   1.00    5.50    --   17.14  77.00-120.00  101
 15  \w     34.00 102.00   1.00    5.50    --   17.14-178.00 -90.00   68
 16  \w      2.00  71.00   1.00    5.50    --   17.14-125.00 160.51   69
 17  \w     35.00 101.00   1.00    5.50    --   17.14 178.00-180.00   66
 18  \w     -2.00  68.00   1.00    5.50    --   17.14-120.00 125.51   70
 19  \w    -20.00   5.00   1.00    5.50    --   17.14 -99.00  30.00   25
;
_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      -0.0090364000
_diffrn_orient_matrix_UB_12      -0.0374407000
_diffrn_orient_matrix_UB_13      -0.0215650000
_diffrn_orient_matrix_UB_21      -0.0659637000
_diffrn_orient_matrix_UB_22      0.0026133000
_diffrn_orient_matrix_UB_23      -0.0022327000
_diffrn_orient_matrix_UB_31      -0.0064682000
_diffrn_orient_matrix_UB_32      0.0256821000
_diffrn_orient_matrix_UB_33      -0.0312164000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            70658
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.824
_diffrn_reflns_theta_min         2.612
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.532
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.47a (Rigaku Oxford Diffraction, 2019)
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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_description       block
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.286
_exptl_crystal_size_mid          0.214
_exptl_crystal_size_min          0.107
_refine_diff_density_max         0.610
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.049
_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     234
_refine_ls_number_reflns         5715
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0388
_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^)+(0.0412P)^2^+2.3832P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1052
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4716
_reflns_number_total             5715
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc04441h2.cif
_cod_data_source_block           compound4b
_cod_database_code               1552453
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C34 H41 N2 P3'
_diffrn_oxdiff_digest_frames
;
014a6c2231e60673a3ba0a2b5582dd226001962acb7
;
_diffrn_oxdiff_digest_hkl
;
01dce08475e98abda01380f1a78eca99c2b341
;
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H9A(0.5) H9B(0.5) C10(0.5) H10A(0.5) H10B(0.5) H10C(0.5) C10B(0.5)
 H10D(0.5) H10E(0.5) H10F(0.5) H12(0.5) H12A(0.5) C14(0.5) H14A(0.5) H14B(0.5)
 H14C(0.5) C14B(0.5) H14D(0.5) H14E(0.5) H14F(0.5) C15(0.5) C16(0.5) H16(0.5)
 C17(0.5) C18(0.5) H18(0.5) C19(0.5) H19(0.5) C20(0.5) H20(0.5) C21(0.5)
 H21A(0.5) H21B(0.5) H21C(0.5)
3.a Ternary CH refined with riding coordinates:
 C9(H9A), C9(H9B), C12(H12), C12(H12A)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C16(H16), C18(H18), C19(H19), C20(H20)
3.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C10B(H10D,H10E,H10F), C11(H11A,H11B,H11C), C13(H13A,H13B,
 H13C), C14(H14A,H14B,H14C), C14B(H14D,H14E,H14F), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              45402
_olex2_date_sample_data_collection 2019-04-05
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.108
_oxdiff_exptl_absorpt_empirical_full_min 0.892