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_1552454
_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         'C38 H39 Mo N2 O5 P3'
_chemical_formula_sum            'C38 H39 Mo N2 O5 P3'
_chemical_formula_weight         792.56
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-05
_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                93.5620(10)
_cell_angle_beta                 101.0270(10)
_cell_angle_gamma                98.0390(10)
_cell_formula_units_Z            4
_cell_length_a                   12.68020(10)
_cell_length_b                   13.72590(10)
_cell_length_c                   23.0210(2)
_cell_measurement_reflns_used    105202
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      32.6150
_cell_measurement_theta_min      3.0660
_cell_volume                     3877.80(6)
_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 0.999
_diffrn_measured_fraction_theta_max 0.952
_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  13.00   1.00   10.00    --  -17.14 -77.00 120.00  101
  2  \w    -75.00 -27.00   1.00   10.00    --  -17.14 131.00  91.94   48
  3  \w     -8.00  86.00   1.00   10.00    --   17.14  57.00 -60.00   94
  4  \w    -51.00  42.00   1.00   10.00    --   17.14 -57.00  30.00   93
  5  \w    -51.00  42.00   1.00   10.00    --   17.14 -57.00 150.00   93
  6  \w     -8.00  86.00   1.00   10.00    --   17.14  57.00  60.00   94
  7  \w     -8.00  86.00   1.00   10.00    --   17.14  57.00-180.00   94
  8  \w    -51.00  42.00   1.00   10.00    --   17.14 -57.00-120.00   93
  9  \w     17.00  91.00   1.00   10.00    --   17.14-154.00  19.71   74
 10  \w    -76.00 -27.00   1.00   10.00    --  -17.14 132.00  -0.72   49
 11  \w    -75.00 -27.00   1.00   10.00    --  -17.14 131.00 -56.72   48
 12  \w    -72.00 -24.00   1.00   10.00    --  -17.14 126.00 178.71   48
 13  \w    -76.00 -27.00   1.00   10.00    --  -17.14 132.00  30.84   49
 14  \w     17.00  91.00   1.00   10.00    --   17.14-154.00 117.32   74
 15  \w     18.00  92.00   1.00   10.00    --   17.14-156.00 -31.31   74
 16  \w      3.00  72.00   1.00   10.00    --   17.14-126.00-157.63   69
 17  \w     35.00 101.00   1.00   10.00    --   17.14 178.00-180.00   66
 18  \w   -102.00 -55.00   1.00   10.00    --  -17.14 178.00  30.00   47
 19  \w    -20.00  56.00   1.00   10.00    --   17.14 -99.00 -90.00   76
 20  \w    -54.00  38.00   1.00   10.00    --   17.14 -38.00-150.00   92
 21  \w    -13.00  88.00   1.00   10.00    --   17.14  77.00 150.00  101
 22  \w     -4.00  88.00   1.00   10.00    --   17.14  38.00   0.00   92
 23  \w    -51.00  42.00   1.00   10.00    --   17.14 -57.00-180.00   93
 24  \w    -68.00   5.00   1.00   10.00    --   17.14   0.00-180.00   73
 25  \w      6.00  76.00   1.00   10.00    --   17.14-132.00-107.65   70
;
_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      0.0570247000
_diffrn_orient_matrix_UB_12      0.0038089000
_diffrn_orient_matrix_UB_13      0.0100663000
_diffrn_orient_matrix_UB_21      -0.0020164000
_diffrn_orient_matrix_UB_22      -0.0490919000
_diffrn_orient_matrix_UB_23      -0.0122560000
_diffrn_orient_matrix_UB_31      0.0084727000
_diffrn_orient_matrix_UB_32      0.0179479000
_diffrn_orient_matrix_UB_33      -0.0272422000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            240247
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.846
_diffrn_reflns_theta_min         2.607
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.505
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.463
_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    1.358
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.196
_exptl_crystal_size_mid          0.167
_exptl_crystal_size_min          0.163
_refine_diff_density_max         0.644
_refine_diff_density_min         -0.581
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     899
_refine_ls_number_reflns         27490
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0279
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0213P)^2^+2.4112P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0619
_refine_ls_wR_factor_ref         0.0652
_reflns_Friedel_coverage         0.000
_reflns_number_gt                24041
_reflns_number_total             27490
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc04441h2.cif
_cod_data_source_block           compound5c
_cod_database_code               1552454
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C38 H39 Mo N2 O5 P3'
_diffrn_oxdiff_digest_frames
;
01ee8ab338ebed4b1acc0e3be826262166019852c52
;
_diffrn_oxdiff_digest_hkl
;
018c117ea63cae84997943726e38057fe48e71
;
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C13(H13), C22(H22), C25(H25), C48(H48), C51(H51), C60(H60), C63(H63)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C18(H18), C19(H19), C20(H20), C29(H29), C30(H30),
 C31(H31), C32(H32), C33(H33), C44(H44), C45(H45), C46(H46), C56(H56), C57(H57),
  C58(H58), C67(H67), C68(H68), C69(H69), C70(H70), C71(H71)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C), C27(H27A,
 H27B,H27C), C49(H49A,H49B,H49C), C50(H50A,H50B,H50C), C52(H52A,H52B,H52C),
 C53(H53A,H53B,H53C), C61(H61A,H61B,H61C), C62(H62A,H62B,H62C), C64(H64A,H64B,
 H64C), C65(H65A,H65B,H65C)
;
_shelx_res_checksum              65123
_olex2_date_sample_data_collection 2019-04-04
_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 1.070
_oxdiff_exptl_absorpt_empirical_full_min 0.940