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_7129169
_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
_chemical_properties_physical    Air-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-07-16
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_audit_update_record
;
2021-07-19 deposited with the CCDC.	2021-10-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.1520(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.04140(10)
_cell_length_b                   14.38220(10)
_cell_length_c                   22.5042(2)
_cell_measurement_reflns_used    46885
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.2570
_cell_measurement_theta_min      3.6200
_cell_volume                     3866.99(5)
_computing_cell_refinement       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_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 0.977
_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    -78.00  25.00   0.50    3.21    --  -47.91  94.00 143.00  206
  2  \w    -13.00  79.00   0.50    3.21    --   47.91 -94.00  32.00  184
  3  \w    -80.00 -19.00   0.50   12.84    --  -91.75  94.00 143.00  122
  4  \w   -163.00 -83.00   0.50   12.84    --  -91.75 -94.00  32.00  160
  5  \w     35.00 106.00   0.50   12.84    --  107.78 -94.00  32.00  142
  6  \w    105.00 178.00   0.50   12.84    --  107.78  94.00 143.00  146
  7  \w    -24.00  28.00   0.50    3.21    --  -47.91  19.00  60.00  104
  8  \w   -119.00 -73.00   0.50    3.21    --  -47.91-125.00-150.00   92
  9  \w    -41.00  25.00   0.50    3.21    --  -47.91  38.00  60.00  132
 10  \w   -119.00 -73.00   0.50    3.21    --  -47.91-125.00 150.00   92
 11  \w   -119.00 -33.00   0.50    3.21    --  -47.91 -57.00 -30.00  172
 12  \w    -26.00  28.00   0.50    3.21    --   47.91 -19.00 120.00  108
 13  \w    -25.00  45.00   0.50    3.21    --   47.91 -38.00  60.00  140
 14  \w    -64.00 -19.00   0.50   12.84    --  -91.75  57.00   0.00   90
 15  \w   -163.00 -73.00   0.50   12.84    --  -91.75-125.00 -60.00  180
 16  \w    -64.00 -19.00   0.50   12.84    --  -91.75  57.00  30.00   90
 17  \w    -64.00 -19.00   0.50   12.84    --  -91.75  57.00  60.00   90
 18  \w   -163.00 -77.00   0.50   12.84    --  -91.75 -57.00-150.00  172
 19  \w    -64.00 -19.00   0.50   12.84    --  -91.75  57.00 120.00   90
 20  \w   -165.00 -78.00   0.50   12.84    --  -91.75 -38.00 -60.00  174
 21  \w   -163.00 -77.00   0.50   12.84    --  -91.75 -57.00-120.00  172
 22  \w    -64.00 -19.00   0.50   12.84    --  -91.75  57.00 150.00   90
 23  \w   -163.00 -69.00   0.50   12.84    --  -91.75 -77.00  90.00  188
 24  \w     93.00 178.00   0.50   12.84    --  107.78  57.00 -90.00  170
 25  \w     35.00 106.00   0.50   12.84    --  107.78 -99.00-150.00  142
 26  \w     35.00 112.00   0.50   12.84    --  107.78-125.00-150.00  154
 27  \w     35.00 107.00   0.50   12.84    --  107.78 -77.00 -30.00  144
 28  \w     35.00  68.00   0.50   12.84    --  107.78 -57.00-120.00   66
 29  \w     35.00  68.00   0.50   12.84    --  107.78 -57.00-150.00   66
 30  \w     35.00 106.00   0.50   12.84    --  107.78 -99.00 -90.00  142
 31  \w     35.00 112.00   0.50   12.84    --  107.78-125.00-180.00  154
 32  \w     35.00 106.00   0.50   12.84    --  107.78 -99.00   0.00  142
 33  \w     35.00 106.00   0.50   12.84    --  107.78 -99.00  90.00  142
 34  \w     35.00 112.00   0.50   12.84    --  107.78-125.00   0.00  154
 35  \w     95.00 178.00   0.50   12.84    --  107.78 125.00-150.00  166
 36  \w     35.00  68.00   0.50   12.84    --  107.78 -57.00   0.00   66
 37  \w     35.00  68.00   0.50   12.84    --  107.78 -57.00-180.00   66
 38  \w   -119.00 -25.00   0.50    3.21    --  -47.91 -77.00 -60.00  188
 39  \w   -119.00 -25.00   0.50    3.21    --  -47.91 -77.00  60.00  188
 40  \w   -119.00 -25.00   0.50    3.21    --  -47.91 -77.00-120.00  188
 41  \w   -119.00 -25.00   0.50    3.21    --  -47.91 -77.00 120.00  188
 42  \w   -119.00 -25.00   0.50    3.21    --  -47.91 -77.00-180.00  188
 43  \w   -119.00 -25.00   0.50    3.21    --  -47.91 -77.00   0.00  188
 44  \w   -121.00 -35.00   0.50    3.21    --  -47.91 -38.00-150.00  172
 45  \w   -119.00 -33.00   0.50    3.21    --  -47.91 -57.00 150.00  172
 46  \w   -163.00-109.00   0.50   12.84    --  -91.75 -77.00-180.00  108
 47  \w   -163.00 -77.00   0.50   12.84    --  -91.75 -57.00  30.00  172
 48  \w   -163.00 -69.00   0.50   12.84    --  -91.75 -77.00 150.00  188
;
_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      0.1277365000
_diffrn_orient_matrix_UB_12      0.0029048000
_diffrn_orient_matrix_UB_13      0.0177622000
_diffrn_orient_matrix_UB_21      -0.0097010000
_diffrn_orient_matrix_UB_22      0.0993305000
_diffrn_orient_matrix_UB_23      0.0244459000
_diffrn_orient_matrix_UB_31      -0.0148994000
_diffrn_orient_matrix_UB_32      -0.0399899000
_diffrn_orient_matrix_UB_33      0.0620084000
_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  0.0406
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            67225
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.346
_diffrn_reflns_theta_min         3.656
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.316
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.788
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
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    1.545
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1824
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Benzene'
_exptl_crystal_size_max          0.108
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.041
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.00044(7)
_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   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     564
_refine_ls_number_reflns         8034
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0361
_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^)+(0.0505P)^2^+1.8092P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1006
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6992
_reflns_number_total             8034
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc05673e2.cif
_cod_data_source_block           7
_cod_database_code               7129169
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C156  H120  B4  F60  N12  O16  '
_chemical_oxdiff_usercomment     chamila
_shelx_estimated_absorpt_t_max   0.948
_shelx_estimated_absorpt_t_min   0.871
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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              43937
_olex2_date_sample_data_collection 2021-07-15
_olex2_date_sample_submission    2021-07-15
_olex2_exptl_crystal_mounting_method
'Hampton Research 20 micron nylon CryoLoop'
_olex2_submission_original_sample_id kre21_20
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_diffrn_reflns_filtered   21845
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.565
_oxdiff_exptl_absorpt_empirical_full_min 0.689