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_7129168
_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         'C20 H30 B N3 O, C6 H6'
_chemical_formula_sum            'C26 H36 B N3 O'
_chemical_formula_weight         417.39
_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                 91.476(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.9123(3)
_cell_length_b                   21.9456(7)
_cell_length_c                   21.0718(8)
_cell_measurement_reflns_used    6589
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      76.1800
_cell_measurement_theta_min      2.9010
_cell_volume                     4582.3(3)
_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      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 0.993
_diffrn_measured_fraction_theta_max 0.949
_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    -51.00  25.00   0.50   12.00    --  -47.70  47.00  35.00  152
  2  \w    -22.00  28.00   0.50   12.00    --  -47.70  19.00  90.00  100
  3  \w    -40.00 -14.00   0.50   32.00    --  -86.25  45.00 150.00   52
  4  \w    -49.00 -24.00   0.50   32.00    --  -86.25  45.00 120.00   50
  5  \w    -51.00 -26.00   0.50   32.00    --  -86.25  47.00  35.00   50
  6  \w    -48.00 -17.00   0.50   32.00    --  -86.25  45.00   0.00   62
  7  \w    -45.00 -14.00   0.50   32.00    --  -86.25  45.00-150.00   62
  8  \w    -49.00 -24.00   0.50   32.00    --  -86.25  45.00-180.00   50
  9  \w   -101.00 -75.00   0.50   32.00    --  -86.25 -47.00-113.00   52
 10  \w   -113.00 -60.00   0.50   12.00    --  -47.70 -47.00-113.00  106
 11  \w   -118.00 -74.00   0.50   12.00    --  -47.70-125.00-180.00   88
 12  \w    -15.00  32.00   0.50   12.00    --   47.70 -47.00-113.00   94
 13  \w     37.00  70.00   0.50   32.00    --  107.75 -61.00 -30.00   66
 14  \w     40.00  67.00   0.50   32.00    --  107.75 -94.00 -90.00   54
 15  \w     81.00 106.00   0.50   32.00    --  107.75 -94.00 -90.00   50
 16  \w     36.00  65.00   0.50   32.00    --  107.75 -61.00  30.00   58
 17  \w     38.00  94.00   0.50   32.00    --  107.75 -77.00  90.00  112
 18  \w     37.00  72.00   0.50   32.00    --  107.75 -61.00 150.00   70
 19  \w     46.00  72.00   0.50   32.00    --  107.75 -61.00 120.00   52
 20  \w     40.00  73.00   0.50   32.00    --  107.75 -61.00  90.00   66
 21  \w     42.00  68.00   0.50   32.00    --  107.75 -61.00   0.00   52
 22  \w     37.00  73.00   0.50   32.00    --  107.75 -61.00 -90.00   72
 23  \w     35.00 107.00   0.50   32.00    --  107.75 -77.00-150.00  144
 24  \w     35.00  73.00   0.50   32.00    --  107.75 -61.00-150.00   76
 25  \w    149.00 175.00   0.50   32.00    --  107.75  45.00 -30.00   52
 26  \w    105.00 144.00   0.50   32.00    --  107.75  45.00 -30.00   78
 27  \w     95.00 172.00   0.50   32.00    --  107.75  47.00  35.00  154
 28  \w     95.00 166.00   0.50   32.00    --  107.75  30.00 150.00  142
 29  \w     48.00  78.00   0.50   12.00    --   47.70  47.00  35.00   60
 30  \w   -119.00 -73.00   0.50   12.00    --  -47.70-125.00  30.00   92
;
_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      0.0203709000
_diffrn_orient_matrix_UB_12      0.0320081000
_diffrn_orient_matrix_UB_13      0.0645987000
_diffrn_orient_matrix_UB_21      -0.1357956000
_diffrn_orient_matrix_UB_22      -0.0257365000
_diffrn_orient_matrix_UB_23      0.0217756000
_diffrn_orient_matrix_UB_31      0.0729329000
_diffrn_orient_matrix_UB_32      -0.0569250000
_diffrn_orient_matrix_UB_33      0.0264819000
_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  0.0826
_diffrn_reflns_av_unetI/netI     0.0708
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            34975
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.151
_diffrn_reflns_theta_min         2.908
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.563
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.889
_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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1808
_exptl_crystal_recrystallization_method 'slow evaporation from benzene'
_exptl_crystal_size_max          0.088
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     555
_refine_ls_number_reflns         9335
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.1086
_refine_ls_R_factor_gt           0.0727
_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^)+(0.1024P)^2^+3.5271P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1909
_refine_ls_wR_factor_ref         0.2144
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6138
_reflns_number_total             9335
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc05673e2.cif
_cod_data_source_block           3
_cod_database_code               7129168
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'B N3 O C20 H30'
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.952
_reflns_odcompleteness_completeness 99.14
_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), C33(H33), C37(H37)
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), C34(H34A,H34B), C35(H35A,H35B), C36(H36A,H36B),
 C38(H38A,H38B), C39(H39A,H39B), C40(H40A,H40B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C24(H24), C25(H25), C26(H26), C27(H27),
 C46(H46), C41(H41), C42(H42), C43(H43), C44(H44), C45(H45), C47(H47), C48(H48),
  C49(H49), C50(H50), C51(H51), C52(H52)
2.d Fitted hexagon refined as free rotating group:
 C46(C41,C42,C43,C44,C45)
2.e Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,
 H12C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C32(H32A,
 H32B,H32C)
;
_shelx_res_checksum              5891
_olex2_exptl_crystal_mounting_method 'Hampton Reasearch 20um nylon loop'
_olex2_submission_original_sample_id kre20_28
_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 1.765
_oxdiff_exptl_absorpt_empirical_full_min 0.482