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_4037771
_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         'C41 H39 B F15 N2 O P'
_chemical_formula_sum            'C41 H39 B F15 N2 O P'
_chemical_formula_weight         902.55
_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_Int_Tables_number      2
_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                86.433(2)
_cell_angle_beta                 84.296(2)
_cell_angle_gamma                88.897(2)
_cell_formula_units_Z            2
_cell_length_a                   10.6793(2)
_cell_length_b                   11.2817(2)
_cell_length_c                   16.7507(4)
_cell_measurement_reflns_used    14850
_cell_measurement_temperature    123.15
_cell_measurement_theta_max      30.8030
_cell_measurement_theta_min      2.1160
_cell_volume                     2004.08(7)
_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 0.9984
_diffrn_measured_fraction_theta_max 0.9984
_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     -6.00  52.00   0.50    5.00    --    5.34  19.00 -30.00  116
  2  \w     -7.00  77.00   0.50    5.00    --    5.34  38.00  60.00  168
  3  \w     39.00  74.00   0.50    5.00    --    5.34  77.00 150.00   70
  4  \w     15.00  62.00   0.50    5.00    --    5.34  57.00 150.00   94
  5  \w    -16.00   9.00   0.50    5.00    --    5.34  77.00 150.00   50
  6  \w    -21.00  37.00   0.50    5.00    --    5.34 -99.00 -60.00  116
  7  \w    -16.00  13.00   0.50    5.00    --   -5.03 -99.00-120.00   58
  8  \w    -10.00  15.00   0.50    5.00    --    5.34 -99.00  30.00   50
;
_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      -0.0489258000
_diffrn_orient_matrix_UB_12      0.0350694000
_diffrn_orient_matrix_UB_13      -0.0154935000
_diffrn_orient_matrix_UB_21      0.0297429000
_diffrn_orient_matrix_UB_22      -0.0043514000
_diffrn_orient_matrix_UB_23      -0.0395168000
_diffrn_orient_matrix_UB_31      -0.0343185000
_diffrn_orient_matrix_UB_32      -0.0521544000
_diffrn_orient_matrix_UB_33      -0.0039997000
_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  0.0292
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            23647
_diffrn_reflns_theta_full        26.3717
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.12
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84065
_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    1.4955
_exptl_crystal_description       plate
_exptl_crystal_F_000             924.9662
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.3303
_refine_diff_density_min         -0.3512
_refine_diff_density_rms         0.0503
_refine_ls_d_res_high            0.8000
_refine_ls_d_res_low             9.5984
_refine_ls_goodness_of_fit_ref   1.0298
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    56
_refine_ls_number_parameters     560
_refine_ls_number_reflns         8182
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0298
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0336
_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^)+(0.0385P)^2^+0.7178P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0843
_refine_ls_wR_factor_ref         0.0879
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              14
_reflns_limit_k_min              -14
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                7037
_reflns_number_total             8182
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo9b03210_si_002.cif
_cod_data_source_block           1aB
_cod_database_code               4037771
_chemical_oxdiff_formula         'C41 H39 B1 F15 N2 O1 P2'
_reflns_odcompleteness_completeness 99.91
_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:
 C59(H59), C56(H56)
2.b Secondary CH2 refined with riding coordinates:
 C52(H52a,H52b), C53(H53a,H53b)
2.c Aromatic/amide H refined with riding coordinates:
 C49(H49), C48(H48), C47(H47)
2.d Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c), C15(H15a,H15b,H15c), C13(H13a,H13b,H13c), C17(H17a,H17b,
 H17c), C16(H16a,H16b,H16c), C11(H11a,H11b,H11c), C61(H61a,H61b,H61c), C60(H60a,
 H60b,H60c), C58(H58a,H58b,H58c), C57(H57a,H57b,H57c)
;
_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 1.427
_oxdiff_exptl_absorpt_empirical_full_min 0.646