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_4037774
_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 Al F15 N2 O3 P, C7 H8'
_chemical_formula_sum            'C49 H47 Al F15 N2 O3 P'
_chemical_formula_weight         1054.86
_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             2019-05-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                83.247(2)
_cell_angle_beta                 75.607(2)
_cell_angle_gamma                66.202(3)
_cell_formula_units_Z            2
_cell_length_a                   11.0128(3)
_cell_length_b                   12.0642(3)
_cell_length_c                   20.6781(6)
_cell_measurement_reflns_used    13002
_cell_measurement_temperature    123.15
_cell_measurement_theta_max      73.7610
_cell_measurement_theta_min      4.0200
_cell_volume                     2434.35(13)
_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      123.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9993
_diffrn_measured_fraction_theta_max 0.9993
_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    -85.00 -52.00   0.50    0.11    --  -42.55-168.00 133.00   66
  2  \w   -101.00 -76.00   0.50    0.11    --  -42.55 168.00 151.00   50
  3  \w    -90.00  -4.00   0.50    0.11    --  -42.55 115.00   7.00  172
  4  \w     46.00  81.00   0.50    0.11    --   42.55 168.00 151.00   70
  5  \w     23.00  48.00   0.50    0.11    --   42.55-115.00 -82.00   50
  6  \w     34.00 118.00   0.50    0.11    --   42.55-168.00 133.00  168
  7  \w     66.00  91.00   0.50    0.45    --   76.50-168.00 133.00   50
  8  \w     57.00  82.00   0.50    0.45    --   76.50-115.00 -82.00   50
  9  \w     77.00 152.00   0.50    0.45    --   76.50 115.00   7.00  150
 10  \w     73.00  98.00   0.50    0.45    --   76.50 168.00 151.00   50
 11  \w   -157.00 -84.00   0.50    0.45    -- -106.00-168.00 133.00  146
 12  \w   -111.00 -31.00   0.50    0.45    -- -106.00 115.00   7.00  160
 13  \w   -113.00 -88.00   0.50    0.45    -- -106.00 168.00 151.00   50
 14  \w   -127.00-102.00   0.50    0.45    -- -106.00-115.00 -82.00   50
 15  \w   -115.00 -77.00   0.50    0.11    --  -42.55-125.00 -30.00   76
 16  \w   -108.00 -71.00   0.50    0.11    --  -42.55-125.00   0.00   74
 17  \w   -115.00 -15.00   0.50    0.11    --  -42.55 -77.00 -90.00  200
 18  \w     23.00 114.00   0.50    0.11    --   42.55  57.00-180.00  182
 19  \w     72.00 109.00   0.50    0.11    --   42.55 125.00 -30.00   74
 20  \w     71.00 115.00   0.50    0.11    --   42.55 125.00-150.00   88
 21  \w     56.00 120.00   0.50    0.45    --   76.50  37.00 -30.00  128
 22  \w   -127.00 -97.00   0.50    0.45    -- -106.00-125.00 -30.00   60
 23  \w   -171.00-144.00   0.50    0.45    -- -106.00 -77.00-150.00   54
 24  \w   -117.00 -85.00   0.50    0.45    -- -106.00 125.00 120.00   64
 25  \w   -174.00 -92.00   0.50    0.45    -- -106.00 -37.00-150.00  164
 26  \w   -177.00 -83.00   0.50    0.45    -- -106.00 -37.00  60.00  188
 27  \w   -161.00 -70.00   0.50    0.45    -- -106.00-125.00   0.00  182
 28  \w   -114.00 -80.00   0.50    0.45    -- -106.00 125.00 -60.00   68
 29  \w   -124.00 -73.00   0.50    0.45    -- -106.00  57.00-120.00  102
 30  \w   -132.00 -32.00   0.50    0.45    -- -106.00  77.00-120.00  200
 31  \w   -177.00 -83.00   0.50    0.45    -- -106.00 -99.00 -60.00  188
 32  \w   -175.00 -93.00   0.50    0.45    -- -106.00 -37.00-180.00  164
 33  \w   -134.00 -37.00   0.50    0.45    -- -106.00  77.00  30.00  194
 34  \w    -81.00 -41.00   0.50    0.45    -- -106.00 125.00 120.00   80
 35  \w   -114.00 -87.00   0.50    0.45    -- -106.00 125.00-120.00   54
 36  \w    -79.00 -40.00   0.50    0.45    -- -106.00 125.00-120.00   78
 37  \w   -160.00 -78.00   0.50    0.45    -- -106.00 -77.00 -30.00  164
 38  \w    -86.00 -57.00   0.50    0.45    -- -106.00 125.00 -90.00   58
 39  \w   -112.00 -59.00   0.50    0.45    -- -106.00 125.00  30.00  106
 40  \w   -119.00 -92.00   0.50    0.45    -- -106.00 -57.00   0.00   54
;
_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      -0.0061775000
_diffrn_orient_matrix_UB_12      0.0675211000
_diffrn_orient_matrix_UB_13      0.0602714000
_diffrn_orient_matrix_UB_21      0.0861884000
_diffrn_orient_matrix_UB_22      0.0639947000
_diffrn_orient_matrix_UB_23      -0.0460663000
_diffrn_orient_matrix_UB_31      -0.1308137000
_diffrn_orient_matrix_UB_32      0.1040714000
_diffrn_orient_matrix_UB_33      -0.0127900000
_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  0.0428
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            30530
_diffrn_reflns_theta_full        68.2517
_diffrn_reflns_theta_max         68.25
_diffrn_reflns_theta_min         4.01
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.583
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80625
_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    1.4390
_exptl_crystal_description       block
_exptl_crystal_F_000             1089.4852
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.7534
_refine_diff_density_min         -0.4420
_refine_diff_density_rms         0.0787
_refine_ls_d_res_high            0.8300
_refine_ls_d_res_low             11.0363
_refine_ls_goodness_of_fit_ref   1.0508
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    70
_refine_ls_number_parameters     651
_refine_ls_number_reflns         8929
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0508
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0557
_refine_ls_shift/su_max          0.0007
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0745P)^2^+3.0822P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1509
_refine_ls_wR_factor_ref         0.1544
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -12
_reflns_limit_k_max              14
_reflns_limit_k_min              -14
_reflns_limit_l_max              24
_reflns_limit_l_min              0
_reflns_number_gt                7972
_reflns_number_total             8929
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo9b03210_si_002.cif
_cod_data_source_block           (k-O-3a)Al(C6F5)3
_cod_database_code               4037774
_chemical_oxdiff_formula         'C42 H39 Al1 F15 N2 O3 p1'
_reflns_odcompleteness_completeness 99.93
_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.a Ternary CH refined with riding coordinates:
 C28(H28), C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b), C9(H9a,H9b)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C4(H4), C3(H3), C66(H66), C70(H70), C67(H67), C68(H68), C69(H69)
2.d Idealised Me refined as rotating group:
 C21(H21a,H21b,H21c), C22(H22a,H22b,H22c), C19(H19a,H19b,H19c), C27(H27a,H27b,
 H27c), C17(H17a,H17b,H17c), C20(H20a,H20b,H20c), C16(H16a,H16b,H16c), C26(H26a,
 H26b,H26c), C30(H30a,H30b,H30c), C29(H29a,H29b,H29c), C71(H71a,H71b,H71c)
;
_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 1.884
_oxdiff_exptl_absorpt_empirical_full_min 0.446