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_7129164
_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'
_chemical_formula_sum            'C20 H30 B N3 O'
_chemical_formula_weight         339.28
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.80100(10)
_cell_length_b                   13.73450(10)
_cell_length_c                   14.01330(10)
_cell_measurement_reflns_used    42383
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.243
_cell_measurement_theta_min      4.482
_cell_volume                     1886.36(3)
_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_temperature      99.95
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            60484
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.328
_diffrn_reflns_theta_min         4.508
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.569
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_description       irregular
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.203
_exptl_crystal_size_mid          0.129
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details
;
 Flack x determined using 1673 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3994
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0271
_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^)+(0.0405P)^2^+0.2628P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0708
_refine_ls_wR_factor_ref         0.0711
_reflns_Friedel_coverage         0.749
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                3938
_reflns_number_total             3994
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc05673e2.cif
_cod_data_source_block           2
_cod_database_code               7129164
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.951
_shelx_estimated_absorpt_t_min   0.893
_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              81422
_olex2_submission_special_instructions 'No special instructions were received'