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_7129167
_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         'C23 H39 B N3 O Si, C F3 O3 S'
_chemical_formula_sum            'C24 H39 B F3 N3 O4 S Si'
_chemical_formula_weight         561.54
_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'
_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                90
_cell_angle_beta                 104.6140(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.7638(2)
_cell_length_b                   8.10800(10)
_cell_length_c                   24.6279(2)
_cell_measurement_reflns_used    12450
_cell_measurement_temperature    99.97(16)
_cell_measurement_theta_max      77.3490
_cell_measurement_theta_min      4.1780
_cell_volume                     2852.70(6)
_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(16)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.945
_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  27.00   0.50    5.30    --  -48.16  19.00  90.00  102
  2  \w    -49.00 -14.00   0.50   21.20    --  -86.25  45.00 150.00   70
  3  \w    -77.00  25.00   0.50    5.30    --  -48.16  91.00 -24.00  204
  4  \w    -80.00 -13.00   0.50   21.20    --  -86.25  91.00 -24.00  134
  5  \w    -49.00 -14.00   0.50   21.20    --  -86.25  45.00-180.00   70
  6  \w   -121.00 -73.00   0.50    5.30    --  -48.16-125.00 -30.00   96
  7  \w   -121.00 -73.00   0.50    5.30    --  -48.16-125.00 -60.00   96
  8  \w   -159.00 -79.00   0.50   21.20    --  -86.25 -91.00-138.00  160
  9  \w    -20.00  77.00   0.50    5.30    --   48.16 -91.00-138.00  194
 10  \w     35.00 106.00   0.50   21.20    --  107.75 -91.00-138.00  142
 11  \w     46.00  73.00   0.50   21.20    --  107.75 -61.00 -60.00   54
 12  \w     45.00  70.00   0.50   21.20    --  107.75 -61.00-120.00   50
 13  \w     35.00  73.00   0.50   21.20    --  107.75 -61.00 -90.00   76
 14  \w     35.00 107.00   0.50   21.20    --  107.75 -77.00-120.00  144
 15  \w     42.00  93.00   0.50   21.20    --  107.75-125.00   0.00  102
 16  \w     35.00  73.00   0.50   21.20    --  107.75 -61.00  60.00   76
 17  \w     35.00 107.00   0.50   21.20    --  107.75 -77.00  30.00  144
 18  \w     39.00  65.00   0.50   21.20    --  107.75 -61.00 120.00   52
 19  \w     35.00  73.00   0.50   21.20    --  107.75 -61.00  30.00   76
 20  \w     35.00  73.00   0.50   21.20    --  107.75 -61.00 -30.00   76
 21  \w     35.00  60.00   0.50   21.20    --  107.75 -61.00   0.00   50
 22  \w     95.00 178.00   0.50   21.20    --  107.75  30.00-120.00  166
 23  \w    101.00 178.00   0.50   21.20    --  107.75  91.00 -24.00  154
 24  \w    144.00 176.00   0.50   21.20    --  107.75  45.00  60.00   64
 25  \w     96.00 139.00   0.50   21.20    --  107.75  45.00  60.00   86
 26  \w     36.00 121.00   0.50    5.30    --   48.16  38.00  60.00  170
;
_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      0.1057983000
_diffrn_orient_matrix_UB_12      0.0246627000
_diffrn_orient_matrix_UB_13      0.0070031000
_diffrn_orient_matrix_UB_21      0.0190010000
_diffrn_orient_matrix_UB_22      -0.1715592000
_diffrn_orient_matrix_UB_23      0.0273916000
_diffrn_orient_matrix_UB_31      -0.0085144000
_diffrn_orient_matrix_UB_32      -0.0778719000
_diffrn_orient_matrix_UB_33      -0.0581310000
_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  0.0453
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            23897
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.584
_diffrn_reflns_theta_min         3.093
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.878
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.583
_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    1.307
_exptl_crystal_description       plate
_exptl_crystal_F_000             1192
_exptl_crystal_recrystallization_method 'Crystallization from benzene'
_exptl_crystal_size_max          0.206
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.015
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         5757
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0420
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0455P)^2^+1.6381P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1113
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4671
_reflns_number_total             5757
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc05673e2.cif
_cod_data_source_block           5
_cod_database_code               7129167
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C96  H156  B4  F12  N12  O16  S4  Si4  '
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.698
_reflns_odcompleteness_completeness 99.18
_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:
 C16(H16), C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C17(H17A,H17B), C18(H18A,
 H18B), C19(H19A,H19B)
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), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              48308
_olex2_date_sample_data_collection 2020-09-11
_olex2_date_sample_submission    2020-09-11
_olex2_exptl_crystal_mounting_method 'MiTeGen 50 um loop'
_olex2_submission_original_sample_id kre20_29
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_diffrn_reflns_filtered   3477
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.055
_oxdiff_exptl_absorpt_empirical_full_min 0.559