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_4037773
_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'
_chemical_formula_sum            'C42 H39 B F15 N2 O3 P'
_chemical_formula_weight         946.56
_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_Int_Tables_number      14
_atom_sites_solution_primary     dual
_audit_creation_date             2019-11-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.214(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.5964(5)
_cell_length_b                   21.5652(12)
_cell_length_c                   18.5448(9)
_cell_measurement_reflns_used    4640
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      75.3130
_cell_measurement_theta_min      4.0770
_cell_volume                     5016.7(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_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      298.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9977
_diffrn_measured_fraction_theta_max 0.9977
_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    -18.00  10.00   0.50    0.50    --   49.84 -48.00 -31.00   56
  2  \w     41.00 110.00   0.50    0.50    --   49.84  48.00 116.00  138
  3  \w    -70.00 -43.00   0.50    0.50    --  -53.09 -48.00 -31.00   54
  4  \w    -22.00  14.00   0.50    0.50    --  -53.09  48.00 116.00   72
  5  \w    106.00 135.00   0.50    0.50    --   66.50  48.00 116.00   58
  6  \w      0.00  71.00   0.50    0.50    --   66.50 -48.00 -31.00  142
  7  \w   -175.00 -96.00   0.50    0.50    -- -105.75 -48.00 -31.00  158
  8  \w    -92.00 -36.00   0.50    0.50    -- -105.75  48.00 116.00  112
  9  \w     93.00 120.00   0.50    0.50    --   49.84 125.00   0.00   54
 10  \w   -123.00 -51.00   0.50    0.50    --  -53.09 -37.00-120.00  144
 11  \w   -111.00 -34.00   0.50    0.50    -- -105.75  57.00 -30.00  154
 12  \w   -164.00-122.00   0.50    0.50    -- -105.75 -19.00-180.00   84
 13  \w   -107.00 -34.00   0.50    0.50    -- -105.75  19.00 150.00  146
 14  \w    -95.00 -46.00   0.50    0.50    -- -105.75  57.00  60.00   98
 15  \w   -110.00 -36.00   0.50    0.50    -- -105.75  19.00 -60.00  148
 16  \w   -103.00 -38.00   0.50    0.50    -- -105.75  37.00 -60.00  130
 17  \w    -87.00 -36.00   0.50    0.50    -- -105.75  37.00 -30.00  102
;
_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      -0.0304577000
_diffrn_orient_matrix_UB_12      -0.0311519000
_diffrn_orient_matrix_UB_13      0.0699496000
_diffrn_orient_matrix_UB_21      0.1121641000
_diffrn_orient_matrix_UB_22      -0.0287825000
_diffrn_orient_matrix_UB_23      0.0118511000
_diffrn_orient_matrix_UB_31      0.0396312000
_diffrn_orient_matrix_UB_32      0.0574698000
_diffrn_orient_matrix_UB_33      0.0439307000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0742
_diffrn_reflns_av_unetI/netI     0.0674
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            34110
_diffrn_reflns_theta_full        68.2429
_diffrn_reflns_theta_max         68.24
_diffrn_reflns_theta_min         4.08
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.312
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46618
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
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    1.2531
_exptl_crystal_description       block
_exptl_crystal_F_000             1945.6612
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.3128
_refine_diff_density_min         -0.4200
_refine_diff_density_rms         0.0690
_refine_ls_d_res_high            0.8300
_refine_ls_d_res_low             10.8432
_refine_ls_goodness_of_fit_ref   0.9904
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    65
_refine_ls_number_parameters     597
_refine_ls_number_reflns         9151
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.9904
_refine_ls_R_factor_all          0.1189
_refine_ls_R_factor_gt           0.0676
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1184P)^2^+0.1506P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1836
_refine_ls_wR_factor_ref         0.2225
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              15
_reflns_limit_h_min              -15
_reflns_limit_k_max              25
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                4595
_reflns_number_total             9151
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo9b03210_si_002.cif
_cod_data_source_block           (k-N-3a)B(C6F5)3
_cod_database_code               4037773
_chemical_oxdiff_formula         'C170 H160 B8 F68 N20 O4 P4 '
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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. Others
 Sof(C64a)=Sof(H64d)=Sof(H64e)=Sof(H64f)=Sof(C62a)=Sof(H62d)=Sof(H62e)=
 Sof(H62f)=1-FVAR(1)
 Sof(C62)=Sof(H62a)=Sof(H62b)=Sof(H62c)=Sof(C64)=Sof(H64a)=Sof(H64b)=Sof(H64c)=
 FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C44(H44), C41(H41)
3.b Secondary CH2 refined with riding coordinates:
 C9(H9a,H9b), C10(H10a,H10b)
3.c Me refined as rotating group:
 C51(H51a,H51b,H51c), C53(H53a,H53b,H53c), C65(H65a,H65b,H65c), C46(H46a,H46b,
 H46c), C52(H52a,H52b,H52c), C42(H42a,H42b,H42c), C45(H45a,H45b,H45c), C62(H62a,
 H62b,H62c), C64(H64a,H64b,H64c), C64a(H64d,H64e,H64f), C62a(H62d,H62e,H62f)
3.d Aromatic/amide H refined with riding coordinates:
 C39(H39), C37(H37), C38(H38)
3.e Idealised Me refined as rotating group:
 C43(H43a,H43b,H43c)
;
_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 1.900
_oxdiff_exptl_absorpt_empirical_full_min 0.556