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_4037770
_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         'C22 H7 B Cl2 F8'
_chemical_formula_sum            'C22 H7 B Cl2 F8'
_chemical_formula_weight         505.02
_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             2018-01-18
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 105.952(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.1406(4)
_cell_length_b                   9.6406(2)
_cell_length_c                   11.2647(3)
_cell_measurement_reflns_used    10285
_cell_measurement_temperature    123.15
_cell_measurement_theta_max      73.9220
_cell_measurement_theta_min      4.1290
_cell_volume                     1998.60(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_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 0.9884
_diffrn_measured_fraction_theta_max 0.9884
_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    -28.00  -3.00   0.50    0.06    --  -42.80  99.00  76.00   50
  2  \w    -62.00 -29.00   0.50    0.25    -- -106.00  37.00 120.00   66
  3  \w    -76.00 -50.00   0.50    0.25    -- -106.00  77.00  30.00   52
  4  \w    -78.00 -34.00   0.50    0.25    -- -106.00  77.00   0.00   88
  5  \w    -96.00 -23.00   0.50    0.06    --  -42.80 125.00 -90.00  146
  6  \w    -64.00  31.00   0.50    0.06    --  -42.80  57.00-180.00  190
  7  \w     77.00 115.00   0.50    0.06    --   42.80 125.00 -90.00   76
  8  \w     84.00 149.00   0.50    0.25    --   76.50  99.00  76.00  130
  9  \w     77.00 116.00   0.50    0.06    --   42.80 125.00 120.00   78
 10  \w     -1.00  34.00   0.50    0.06    --   42.80 -99.00 -29.00   70
 11  \w     76.00 107.00   0.50    0.25    --   76.50 -99.00 -29.00   62
 12  \w    -74.00 -38.00   0.50    0.25    -- -106.00 125.00-180.00   72
 13  \w    -57.00 -32.00   0.50    0.25    -- -106.00  57.00-180.00   50
 14  \w    -63.00 -28.00   0.50    0.25    -- -106.00   0.00-150.00   70
 15  \w   -112.00 -85.00   0.50    0.06    --  -42.80-125.00  30.00   54
 16  \w   -133.00 -85.00   0.50    0.25    -- -106.00 -37.00   0.00   96
 17  \w   -128.00 -57.00   0.50    0.25    -- -106.00  37.00 -30.00  142
 18  \w   -100.00 -50.00   0.50    0.25    -- -106.00  37.00  30.00  100
 19  \w    -93.00 -67.00   0.50    0.25    -- -106.00  37.00 120.00   52
 20  \w    -86.00 -41.00   0.50    0.25    -- -106.00  19.00 150.00   90
 21  \w   -109.00 -69.00   0.50    0.25    -- -106.00  99.00  76.00   80
 22  \w   -121.00 -80.00   0.50    0.25    -- -106.00 125.00  30.00   82
 23  \w    -93.00 -68.00   0.50    0.25    -- -106.00 125.00 -30.00   50
 24  \w   -135.00 -89.00   0.50    0.25    -- -106.00  77.00  30.00   92
 25  \w   -128.00 -69.00   0.50    0.25    -- -106.00  77.00  90.00  118
 26  \w   -125.00-100.00   0.50    0.25    -- -106.00  77.00 150.00   50
 27  \w   -126.00 -99.00   0.50    0.25    -- -106.00  19.00 150.00   54
 28  \w   -174.00 -88.00   0.50    0.25    -- -106.00 -99.00 -29.00  172
 29  \w   -137.00 -89.00   0.50    0.25    -- -106.00 -37.00 -30.00   96
 30  \w   -129.00 -82.00   0.50    0.25    -- -106.00  29.00 -72.92   94
 31  \w   -119.00 -94.00   0.50    0.25    -- -106.00   0.00-150.00   50
 32  \w   -116.00 -90.00   0.50    0.25    -- -106.00  57.00-180.00   52
 33  \w   -109.00 -83.00   0.50    0.25    -- -106.00 125.00-180.00   52
 34  \w   -177.00-102.00   0.50    0.25    -- -106.00 -57.00 -90.00  150
 35  \w   -144.00-119.00   0.50    0.25    -- -106.00 -99.00 -60.00   50
 36  \w   -150.00-124.00   0.50    0.25    -- -106.00 -57.00-120.00   52
 37  \w   -157.00-132.00   0.50    0.25    -- -106.00 -77.00 -60.00   50
 38  \w   -176.00-150.00   0.50    0.25    -- -106.00 -99.00 -60.00   52
 39  \w   -165.00-139.00   0.50    0.25    -- -106.00 -57.00-150.00   52
 40  \w   -173.00-148.00   0.50    0.25    -- -106.00 -99.00-180.00   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      -0.0035765000
_diffrn_orient_matrix_UB_12      0.1391358000
_diffrn_orient_matrix_UB_13      0.0653631000
_diffrn_orient_matrix_UB_21      -0.0488385000
_diffrn_orient_matrix_UB_22      0.0602680000
_diffrn_orient_matrix_UB_23      -0.1211283000
_diffrn_orient_matrix_UB_31      -0.0678932000
_diffrn_orient_matrix_UB_32      -0.0505569000
_diffrn_orient_matrix_UB_33      0.0356313000
_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  0.0609
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19978
_diffrn_reflns_theta_full        74.3352
_diffrn_reflns_theta_max         74.34
_diffrn_reflns_theta_min         4.81
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.700
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50558
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.31d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.6782
_exptl_crystal_description       block
_exptl_crystal_F_000             1007.0254
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.2902
_refine_diff_density_min         -0.2824
_refine_diff_density_rms         0.0618
_refine_ls_d_res_high            0.8007
_refine_ls_d_res_low             9.2018
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0411
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    14
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4016
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0411
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0391
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0621P)^2^+0.5942P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1084
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              22
_reflns_limit_h_min              -23
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                3660
_reflns_number_total             4016
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo9b03210_si_002.cif
_cod_data_source_block           B(1,3-dichloroazulenyl)(p-HC6F4)2
_cod_original_cell_volume        1998.60(9)
_cod_database_code               4037770
_chemical_oxdiff_formula         'C22 H7 B1 Cl2 F8'
_reflns_odcompleteness_completeness 98.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C21(H21), C4(H4), C7(H7), C6(H6), C5(H5), C15(H15)
;
_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 3.319
_oxdiff_exptl_absorpt_empirical_full_min 0.358