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_1552451
_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 H41 Fe N2 O4 P3, C7 H8'
_chemical_formula_sum            'C45 H49 Fe N2 O4 P3'
_chemical_formula_weight         830.62
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-02-11
_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                 96.0125(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.83254(14)
_cell_length_b                   24.9423(3)
_cell_length_c                   16.03521(18)
_cell_measurement_reflns_used    93941
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      32.6160
_cell_measurement_theta_min      2.9980
_cell_volume                     4308.70(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.39a (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 0.970
_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    -72.00 -24.00   1.00   34.42    --  -17.14 126.00  80.50   48
  2  \w    -42.00  51.00   1.00   34.42    --  -17.14  57.00  60.00   93
  3  \w     -8.00  86.00   1.00   34.42    --   17.14  57.00 150.00   94
  4  \w    -51.00  42.00   1.00   34.42    --   17.14 -57.00 150.00   93
  5  \w     -4.00  88.00   1.00   34.42    --   17.14  38.00  90.00   92
  6  \w      6.00  75.00   1.00   34.42    --   17.14-131.00 -76.29   69
  7  \w     -8.00  86.00   1.00   34.42    --   17.14  57.00-150.00   94
  8  \w    -54.00  47.00   1.00   34.42    --   17.14 -77.00 -30.00  101
  9  \w    -13.00  88.00   1.00   34.42    --   17.14  77.00 -60.00  101
 10  \w    -76.00 -27.00   1.00   34.42    --  -17.14 132.00 125.75   49
 11  \w    -74.00 -27.00   1.00   34.42    --  -17.14 130.00 -14.47   47
 12  \w    -88.00  13.00   1.00   34.42    --  -17.14 -77.00 -90.00  101
 13  \w     -1.00  69.00   1.00   34.42    --   17.14-121.00 -15.47   70
 14  \w      6.00  76.00   1.00   34.42    --   17.14-132.00 104.16   70
 15  \w     34.00 102.00   1.00   34.42    --   17.14-178.00-120.00   68
 16  \w     -1.00  69.00   1.00   34.42    --   17.14-121.00  63.35   70
 17  \w   -102.00 -55.00   1.00   34.42    --  -17.14 178.00 -90.00   47
 18  \w    -86.00   8.00   1.00   34.42    --  -17.14 -57.00  60.00   94
 19  \w     -8.00  64.00   1.00   34.42    --   17.14-113.00  83.47   72
 20  \w     13.00  85.00   1.00   34.42    --   17.14-147.00 143.11   72
 21  \w     10.00  79.00   1.00   34.42    --   17.14-138.00  36.10   69
 22  \w    -11.00  62.00   1.00   34.42    --   17.14-110.00 -43.80   73
 23  \w      3.00  72.00   1.00   34.42    --   17.14-126.00-130.76   69
 24  \w    -88.00 -16.00   1.00   34.42    --  -17.14 -38.00  90.00   72
 25  \w    -20.00  56.00   1.00   34.42    --   17.14 -99.00-180.00   76
;
_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      -0.0201123000
_diffrn_orient_matrix_UB_12      -0.0264147000
_diffrn_orient_matrix_UB_13      0.0077912000
_diffrn_orient_matrix_UB_21      -0.0615321000
_diffrn_orient_matrix_UB_22      0.0071467000
_diffrn_orient_matrix_UB_23      -0.0154857000
_diffrn_orient_matrix_UB_31      0.0119594000
_diffrn_orient_matrix_UB_32      -0.0077261000
_diffrn_orient_matrix_UB_33      -0.0409732000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            261252
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.880
_diffrn_reflns_theta_min         2.526
_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  0.777
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.39a (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 orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.151
_exptl_crystal_size_min          0.142
_refine_diff_density_max         0.545
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     506
_refine_ls_number_reflns         15612
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0311
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0346P)^2^+2.2156P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0789
_refine_ls_wR_factor_ref         0.0827
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13655
_reflns_number_total             15612
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc04441h2.cif
_cod_data_source_block           compound5b
_cod_original_cell_volume        4308.69(9)
_cod_database_code               1552451
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C44 H49 Fe N2 O3 P3'
_diffrn_oxdiff_digest_frames
;
0184baab6d09e2b3f7627ce149193a7f9701984d1b3
;
_diffrn_oxdiff_digest_hkl
;
01032c01b9d7f2128de70d05e56bc6919ba88a
;
_reflns_odcompleteness_completeness 99.90
_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)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C18(H18), C19(H19), C20(H20), C29(H29), C31(H31),
 C32(H32), C33(H33), C40(H40), C41(H41), C42(H42), C43(H43), C44(H44)
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), C34(H34A,H34B,H34C), C45(H45A,H45B,H45C)
;
_shelx_res_checksum              28337
_olex2_date_sample_data_collection 2019-02-08
_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 1.251
_oxdiff_exptl_absorpt_empirical_full_min 0.893