Carbon Monoxide Bond Cleavage Mediated by an Intramolecular Frustrated Lewis Pair: Access to New B/N Heterocycles via Selective Incorporation of Single Carbon Atoms
Krempner, Clemens; Manankandayalage, Chamila; Unruh, Daniel K.; Chemical Communications  (2021) –; doi:10.1039/D1CC05673E

data_7129172
_publ_section_title
;
 Carbon Monoxide Bond Cleavage Mediated by an Intramolecular Frustrated
 Lewis Pair: Access to New B/N Heterocycles via Selective Incorporation of
 Single Carbon Atoms
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC05673E
_journal_year                    2021
_chemical_formula_moiety         'C38 H30 B2 F15 N3 O4'
_chemical_formula_sum            'C38 H30 B2 F15 N3 O4'
_chemical_formula_weight         899.27
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-04-28
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_audit_update_record
;
2021-06-23 deposited with the CCDC.	2021-10-29 downloaded from the CCDC.
;
_cell_angle_alpha                102.5980(10)
_cell_angle_beta                 95.5420(10)
_cell_angle_gamma                99.7630(10)
_cell_formula_units_Z            2
_cell_length_a                   10.30660(10)
_cell_length_b                   10.5767(2)
_cell_length_c                   17.8236(2)
_cell_measurement_reflns_used    23911
_cell_measurement_temperature    99.97(17)
_cell_measurement_theta_max      77.2830
_cell_measurement_theta_min      2.5520
_cell_volume                     1850.60(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(17)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.974
_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    -24.00  28.00   0.50    0.14    --  -47.95  19.00 -30.00  104
  2  \w    -41.00  25.00   0.50    0.14    --  -47.95  38.00-150.00  132
  3  \w    -26.00  28.00   0.50    0.14    --   47.95 -19.00   0.00  108
  4  \w     28.00  91.00   0.50    0.14    --   47.95-116.00 -87.00  126
  5  \w     35.00 109.00   0.50    0.56    --  107.75-116.00 -87.00  148
  6  \w     81.00 106.00   0.50    0.56    --  107.75 -94.00-180.00   50
  7  \w     36.00  65.00   0.50    0.56    --  107.75 -94.00-180.00   58
  8  \w     35.00  73.00   0.50    0.56    --  107.75 -61.00-120.00   76
  9  \w     35.00  73.00   0.50    0.56    --  107.75 -61.00 -90.00   76
 10  \w     35.00  73.00   0.50    0.56    --  107.75 -61.00 -30.00   76
 11  \w     35.00  73.00   0.50    0.56    --  107.75 -61.00   0.00   76
 12  \w     35.00  73.00   0.50    0.56    --  107.75 -61.00  60.00   76
 13  \w     74.00 100.00   0.50    0.56    --  107.75 -94.00  90.00   52
 14  \w     70.00 107.00   0.50    0.56    --  107.75-106.00 124.39   74
 15  \w     55.00 139.00   0.50    0.56    --  107.75-165.00 125.00  168
 16  \w     55.00 122.00   0.50    0.14    --   47.95-165.00 125.00  134
 17  \w     43.00 124.00   0.50    0.56    --  107.75-141.00  43.84  162
 18  \w     35.00  73.00   0.50    0.56    --  107.75 -61.00  90.00   76
 19  \w     37.00  63.00   0.50    0.56    --  107.75-106.00 124.39   52
 20  \w     37.00  68.00   0.50    0.56    --  107.75 -61.00 120.00   62
 21  \w     94.00 178.00   0.50    0.56    --  107.75  15.00   0.00  168
 22  \w    101.00 178.00   0.50    0.56    --  107.75 116.00   0.00  154
 23  \w     95.00 178.00   0.50    0.56    --  107.75  30.00-120.00  166
 24  \w     95.00 178.00   0.50    0.56    --  107.75 125.00 -60.00  166
 25  \w     95.00 178.00   0.50    0.56    --  107.75  45.00  90.00  166
 26  \w     98.00 177.00   0.50    0.56    --  107.75  30.00  30.00  158
 27  \w    103.00 170.00   0.50    0.56    --  107.75  30.00 120.00  134
 28  \w     69.00 119.00   0.50    0.14    --   47.95 165.00 147.00  100
 29  \w     69.00 155.00   0.50    0.56    --  107.75 165.00 147.00  172
 30  \w     37.00  73.00   0.50    0.56    --  107.75 -61.00 -60.00   72
 31  \w     35.00 112.00   0.50    0.56    --  107.75-125.00 -30.00  154
 32  \w     35.00 112.00   0.50    0.56    --  107.75-125.00-180.00  154
 33  \w     35.00 102.00   0.50    0.56    --  107.75 -94.00-150.00  134
 34  \w    -41.00  25.00   0.50    0.14    --  -47.95  38.00  90.00  132
 35  \w    -49.00 -14.00   0.50    0.56    --  -86.25  45.00 120.00   70
 36  \w    -83.00  -6.00   0.50    0.14    --  -47.95 116.00   0.00  154
 37  \w    -83.00 -13.00   0.50    0.56    --  -86.25 116.00   0.00  140
 38  \w   -113.00 -33.00   0.50    0.56    --  -86.25 165.00 147.00  160
 39  \w   -113.00 -33.00   0.50    0.14    --  -47.95 165.00 147.00  160
 40  \w   -158.00 -73.00   0.50    0.56    --  -86.25 -45.00 -30.00  170
 41  \w   -120.00 -73.00   0.50    0.14    --  -47.95-125.00-120.00   94
 42  \w   -159.00 -79.00   0.50    0.56    --  -86.25-116.00 -87.00  160
 43  \w   -119.00 -47.00   0.50    0.14    --  -47.95-165.00 125.00  144
 44  \w   -120.00 -73.00   0.50    0.14    --  -47.95-125.00 120.00   94
 45  \w   -138.00 -47.00   0.50    0.56    --  -86.25-165.00 125.00  182
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0992195000
_diffrn_orient_matrix_UB_12      0.1016588000
_diffrn_orient_matrix_UB_13      0.0641218000
_diffrn_orient_matrix_UB_21      0.0904313000
_diffrn_orient_matrix_UB_22      0.0284350000
_diffrn_orient_matrix_UB_23      -0.0607466000
_diffrn_orient_matrix_UB_31      -0.0737123000
_diffrn_orient_matrix_UB_32      0.1096569000
_diffrn_orient_matrix_UB_33      -0.0140174000
_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  0.0376
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            36622
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.526
_diffrn_reflns_theta_min         2.565
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.375
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.679
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_recrystallization_method 'Slow evaporation from benzene'
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.088
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.00105(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     564
_refine_ls_number_reflns         7654
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0338
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0402P)^2^+0.6608P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0878
_refine_ls_wR_factor_ref         0.0902
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6908
_reflns_number_total             7654
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc05673e2.cif
_cod_data_source_block           8
_cod_database_code               7129172
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C78  H60  B4  F30  N6  O6  '
_shelx_estimated_absorpt_t_max   0.889
_shelx_estimated_absorpt_t_min   0.810
_reflns_odcompleteness_completeness 99.96
_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:
 C13(H13), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C18(H18A,H18B), C19(H19A,
 H19B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              68433
_olex2_exptl_crystal_mounting_method 'MiTeGen 100 micron loop'
_olex2_submission_original_sample_id kre20_27
_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 1.340
_oxdiff_exptl_absorpt_empirical_full_min 0.657