Axial Chirality around N–P Bonds Induced by Complexation between E(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub> (E = B, Al) and an N-Phosphine-Oxide-Substituted Imidazolinylidene: A Key Intermediate in the Catalytic Phosphinoylation of CO<sub>2</sub>.
Asada, Takahiro; Hoshimoto, Yoichi; Kawakita, Takahiro; Kinoshita, Takuya; Ogoshi, Sensuke; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03210

data_4037772
_publ_section_title
;
 Axial Chirality around N--P Bonds Induced by Complexation between
 E(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub> (E = B, Al) and an
 N-Phosphine-Oxide-Substituted Imidazolinylidene: A Key Intermediate in
 the Catalytic Phosphinoylation of CO<sub>2</sub>.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03210
_journal_year                    2020
_chemical_formula_moiety         'C42 H39 B F15 N2 O3 P, C H2 Cl2'
_chemical_formula_sum            'C43 H41 B Cl2 F15 N2 O3 P'
_chemical_formula_weight         1031.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.002(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5340(3)
_cell_length_b                   21.0599(6)
_cell_length_c                   20.8720(6)
_cell_measurement_reflns_used    13276
_cell_measurement_temperature    123.15
_cell_measurement_theta_max      31.0530
_cell_measurement_theta_min      2.1430
_cell_volume                     4612.7(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      123.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9975
_diffrn_measured_fraction_theta_max 0.9975
_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    -54.00   5.00   0.50   60.00    --   -2.87 -38.00-120.00  118
  2  \w     -3.00  32.00   0.50   60.00    --    3.18 -99.00-150.00   70
  3  \w    -26.00  28.00   0.50   60.00    --   -2.87 -99.00   0.00  108
  4  \w    -22.00   4.00   0.50   60.00    --    3.18 -99.00  60.00   52
  5  \w     15.00  67.00   0.50   60.00    --    3.18  38.00-180.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0024452000
_diffrn_orient_matrix_UB_12      -0.0316008000
_diffrn_orient_matrix_UB_13      -0.0116223000
_diffrn_orient_matrix_UB_21      0.0455066000
_diffrn_orient_matrix_UB_22      -0.0077870000
_diffrn_orient_matrix_UB_23      0.0258398000
_diffrn_orient_matrix_UB_31      -0.0499094000
_diffrn_orient_matrix_UB_32      -0.0087021000
_diffrn_orient_matrix_UB_33      0.0189851000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            36267
_diffrn_reflns_theta_full        26.3726
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.10
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.278
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83480
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.4852
_exptl_crystal_description       plate
_exptl_crystal_F_000             2107.2362
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.7938
_refine_diff_density_min         -0.6847
_refine_diff_density_rms         0.0654
_refine_ls_d_res_high            0.8000
_refine_ls_d_res_low             9.7153
_refine_ls_goodness_of_fit_ref   1.0293
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    59
_refine_ls_number_parameters     614
_refine_ls_number_reflns         9421
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0293
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0376P)^2^+2.9533P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.0951
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -13
_reflns_limit_k_max              26
_reflns_limit_k_min              0
_reflns_limit_l_max              26
_reflns_limit_l_min              -10
_reflns_number_gt                7746
_reflns_number_total             9421
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo9b03210_si_002.cif
_cod_data_source_block           5a
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               4037772
_chemical_oxdiff_formula         'C43 H41 B1 F15 N2 O3 P1 Cl2'
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.a Ternary CH refined with riding coordinates:
 C62(H62), C59(H59)
2.b Secondary CH2 refined with riding coordinates:
 C46(H46a,H46b), C47(H47a,H47b), C66(H66a,H66b)
2.c Aromatic/amide H refined with riding coordinates:
 C42(H42), C40(H40), C41(H41)
2.d Idealised Me refined as rotating group:
 C64(H64a,H64b,H64c), C63(H63a,H63b,H63c), C51(H51a,H51b,H51c), C52(H52a,H52b,
 H52c), C57(H57a,H57b,H57c), C56(H56a,H56b,H56c), C54(H54a,H54b,H54c), C61(H61a,
 H61b,H61c), C60(H60a,H60b,H60c), C55(H55a,H55b,H55c)
;
_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 1.204
_oxdiff_exptl_absorpt_empirical_full_min 0.754