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_7129166
_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         'C21 H33 B N3 O, C F3 O3 S'
_chemical_formula_sum            'C22 H33 B F3 N3 O4 S'
_chemical_formula_weight         503.38
_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             2021-04-28
_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                 104.245(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6168(3)
_cell_length_b                   8.1837(2)
_cell_length_c                   24.2230(5)
_cell_measurement_reflns_used    9309
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      76.9410
_cell_measurement_theta_min      3.6150
_cell_volume                     2424.17(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.963
_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  26.00   0.50   12.00    --  -47.98   8.00   6.00  100
  2  \w    -41.00  25.00   0.50   12.00    --  -47.98  38.00 150.00  132
  3  \w     29.00 122.00   0.50   12.00    --   47.98   8.00   6.00  186
  4  \w     89.00 178.00   0.50   30.00    --  107.75   8.00   6.00  178
  5  \w     95.00 178.00   0.50   30.00    --  107.75  30.00 -90.00  166
  6  \w     95.00 178.00   0.50   30.00    --  107.75  30.00-120.00  166
  7  \w     34.00  96.00   0.50   12.00    --   47.98-125.00   0.00  124
  8  \w     35.00  73.00   0.50   30.00    --  107.75 -61.00   0.00   76
  9  \w     35.00  73.00   0.50   30.00    --  107.75 -61.00 -30.00   76
 10  \w     35.00  73.00   0.50   30.00    --  107.75 -61.00 -90.00   76
 11  \w     35.00 106.00   0.50   30.00    --  107.75 -94.00 -60.00  142
 12  \w     35.00 112.00   0.50   30.00    --  107.75-125.00-180.00  154
 13  \w     35.00 112.00   0.50   30.00    --  107.75-125.00 -90.00  154
 14  \w     35.00 106.00   0.50   30.00    --  107.75 -94.00-180.00  142
 15  \w    -26.00  28.00   0.50   12.00    --   47.98  -8.00-168.00  108
 16  \w    -24.00  28.00   0.50   12.00    --  -47.98  19.00-150.00  104
 17  \w    -86.00 -13.00   0.50   30.00    --  -86.25 125.00  60.00  146
 18  \w   -122.00 -29.00   0.50   12.00    --  -47.98  -8.00-168.00  186
 19  \w     25.00 109.00   0.50   12.00    --   47.98  77.00  90.00  168
 20  \w     35.00 106.00   0.50   30.00    --  107.75 -94.00  90.00  142
 21  \w   -160.00 -67.00   0.50   30.00    --  -86.25  -8.00-168.00  186
;
_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      0.1125628000
_diffrn_orient_matrix_UB_12      0.0017864000
_diffrn_orient_matrix_UB_13      -0.0141363000
_diffrn_orient_matrix_UB_21      0.0563967000
_diffrn_orient_matrix_UB_22      -0.0204501000
_diffrn_orient_matrix_UB_23      0.0636804000
_diffrn_orient_matrix_UB_31      -0.0049861000
_diffrn_orient_matrix_UB_32      -0.1871201000
_diffrn_orient_matrix_UB_33      -0.0070418000
_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  0.0588
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            23352
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.460
_diffrn_reflns_theta_min         3.641
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.690
_exptl_absorpt_correction_T_max  0.93384
_exptl_absorpt_correction_T_min  0.93384
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Spherical absorption correction
using equivalent radius and absorption coefficient.
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    1.379
_exptl_crystal_description       needle
_exptl_crystal_F_000             1064
_exptl_crystal_recrystallization_method 'Slow evaporation from hexanes'
_exptl_crystal_size_max          0.241
_exptl_crystal_size_mid          0.037
_exptl_crystal_size_min          0.009
_exptl_crystal_size_rad          0.027
_refine_diff_density_max         0.722
_refine_diff_density_min         -0.550
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4958
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0563
_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^)+(0.1002P)^2^+0.9177P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1554
_refine_ls_wR_factor_ref         0.1642
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4017
_reflns_number_total             4958
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc05673e2.cif
_cod_data_source_block           12
_cod_database_code               7129166
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C88  H132  B4  F12  N16  O12  S4  '
_reflns_odcompleteness_completeness 99.85
_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), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              82895
_olex2_date_sample_data_collection 2020-12-10
_olex2_date_sample_submission    2020-12-10
_olex2_exptl_crystal_mounting_method 'MiTiGen 50 um MicroLoop'
_olex2_submission_original_sample_id kre20_41
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.834
_oxdiff_exptl_absorpt_empirical_full_min 0.554