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_1552450
_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         'C37 H39 Fe N2 O4 P3, C7 H8'
_chemical_formula_sum            'C44 H47 Fe N2 O4 P3'
_chemical_formula_weight         816.59
_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             2019-03-18
_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                 96.991(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9413(2)
_cell_length_b                   23.5902(4)
_cell_length_c                   16.2953(3)
_cell_measurement_reflns_used    42796
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      32.6560
_cell_measurement_theta_min      3.0440
_cell_volume                     4174.67(13)
_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 0.999
_diffrn_measured_fraction_theta_max 0.955
_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    -42.00  51.00   1.00    5.76    --  -17.14  57.00 150.00   93
  2  \w    -91.00 -39.00   1.00    5.76    --  -17.14 154.00 126.53   52
  3  \w    -88.00  13.00   1.00    5.76    --  -17.14 -77.00 150.00  101
  4  \w     -8.00  86.00   1.00    5.76    --   17.14  57.00 120.00   94
  5  \w    -54.00  38.00   1.00    5.76    --   17.14 -38.00-180.00   92
  6  \w    -51.00  42.00   1.00    5.76    --   17.14 -57.00 -60.00   93
  7  \w     -4.00  88.00   1.00    5.76    --   17.14  41.00 -96.00   92
  8  \w     -4.00  88.00   1.00    5.76    --   17.14  38.00 -30.00   92
  9  \w     -8.00  86.00   1.00    5.76    --   17.14  57.00  30.00   94
 10  \w      6.00  75.00   1.00    5.76    --   17.14-131.00 100.45   69
 11  \w    -75.00 -27.00   1.00    5.76    --  -17.14 131.00-156.20   48
 12  \w    -91.00 -61.00   1.00    5.76    --  -17.14 154.00  82.56   30
;
_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      -0.0545427000
_diffrn_orient_matrix_UB_12      0.0152282000
_diffrn_orient_matrix_UB_13      0.0048768000
_diffrn_orient_matrix_UB_21      0.0183620000
_diffrn_orient_matrix_UB_22      0.0017222000
_diffrn_orient_matrix_UB_23      0.0431947000
_diffrn_orient_matrix_UB_31      0.0308984000
_diffrn_orient_matrix_UB_32      0.0258674000
_diffrn_orient_matrix_UB_33      -0.0057750000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            127619
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.838
_diffrn_reflns_theta_min         2.534
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.520
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.515
_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    1.299
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.368
_exptl_crystal_size_mid          0.267
_exptl_crystal_size_min          0.184
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     549
_refine_ls_number_reflns         14823
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0344
_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^)+(0.0284P)^2^+2.2181P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0756
_refine_ls_wR_factor_ref         0.0823
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12232
_reflns_number_total             14823
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc04441h2.cif
_cod_data_source_block           compound5a
_cod_database_code               1552450
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C44 H47 Fe N2 O4 P3'
_diffrn_oxdiff_digest_frames
;
013276e1a369d73b85ee513372dafeaa30000273358
;
_diffrn_oxdiff_digest_hkl
;
01f7f3ba0b4390b256e94d13cbb7f2d5fb7236
;
_reflns_odcompleteness_completeness 99.88
_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. Restrained distances
 C38-C39 \\sim C38A-C39A
 with sigma of 0.02
 C38-C43 \\sim C38A-C43A
 with sigma of 0.02
 C38-C44 \\sim C38A-C44A
 with sigma of 0.02
 C39-C40 \\sim C39A-C40A
 with sigma of 0.02
 C40-C41 \\sim C40A-C41A
 with sigma of 0.02
 C41-C42 \\sim C41A-C42A
 with sigma of 0.02
 C42-C43 \\sim C42A-C43A
 with sigma of 0.02
 C38-C40 \\sim C38A-C40A
 with sigma of 0.04
 C38-C42 \\sim C38A-C42A
 with sigma of 0.04
 C39-C41 \\sim C39A-C41A
 with sigma of 0.04
 C39-C43 \\sim C39A-C43A
 with sigma of 0.04
 C39-C44 \\sim C39A-C44A
 with sigma of 0.04
 C40-C42 \\sim C40A-C42A
 with sigma of 0.04
 C41-C43 \\sim C41A-C43A
 with sigma of 0.04
 C43-C44 \\sim C43A-C44A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C43) = Uanis(C43A)
Uanis(C39) = Uanis(C39A)
4. Others
 Sof(C43A)=Sof(H43A)=Sof(C38A)=Sof(C39A)=Sof(H39A)=Sof(C44A)=Sof(H44D)=
 Sof(H44E)=Sof(H44F)=Sof(C40A)=Sof(H40A)=Sof(C42A)=Sof(H42A)=Sof(C41A)=
 Sof(H41A)=1-FVAR(1)
 Sof(C38)=Sof(C39)=Sof(H39)=Sof(C40)=Sof(H40)=Sof(C41)=Sof(H41)=Sof(C42)=
 Sof(H42)=Sof(C43)=Sof(H43)=Sof(C44)=Sof(H44A)=Sof(H44B)=Sof(H44C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C10(H10), C13(H13), C22(H22), C25(H25)
5.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), C39(H39), C40(H40), C41(H41), C42(H42), C43(H43),
  C43A(H43A), C39A(H39A), C40A(H40A), C42A(H42A), C41A(H41A)
5.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), C44(H44A,H44B,H44C), C44A(H44D,H44E,H44F)
;
_shelx_res_checksum              2700
_olex2_date_sample_data_collection 2019-03-18
_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 0.881