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_7129165
_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 H31 B N3 O, C F3 O3 S, 2(C6 H6)'
_chemical_formula_sum            'C33 H43 B F3 N3 O4 S'
_chemical_formula_weight         645.57
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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                87.344(2)
_cell_angle_beta                 86.740(2)
_cell_angle_gamma                80.246(2)
_cell_formula_units_Z            2
_cell_length_a                   10.5533(3)
_cell_length_b                   11.0017(2)
_cell_length_c                   13.6961(4)
_cell_measurement_reflns_used    16375
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.403
_cell_measurement_theta_min      3.218
_cell_volume                     1563.56(7)
_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      100.20
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.960
_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  0.0535
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            36700
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.783
_diffrn_reflns_theta_min         3.234
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.437
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.345
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.40.70a (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            'translucent colourless'
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_description       irregular
_exptl_crystal_F_000             684
_exptl_crystal_size_max          0.264
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.113
_refine_diff_density_max         1.082
_refine_diff_density_min         -0.556
_refine_diff_density_rms         0.110
_refine_ls_extinction_coef       0.0030(8)
_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   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     443
_refine_ls_number_reflns         6402
_refine_ls_number_restraints     174
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0836
_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^)+(0.1519P)^2^+2.0098P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2380
_refine_ls_wR_factor_ref         0.2439
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5692
_reflns_number_total             6402
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc05673e2.cif
_cod_data_source_block           6
_cod_database_code               7129165
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.703
_shelx_estimated_absorpt_t_max   0.854
_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, All O(H) groups
2. Uiso/Uaniso restraints and constraints
C28B \\sim C29B \\sim C30B \\sim C31B \\sim C32B \\sim C33B \\sim C28A \\sim
C29A \\sim C30A \\sim C31A \\sim C32A \\sim C33A: within 2A with sigma of 0.02
and sigma for terminal atoms of 0.04 within 2A
3. Others
 Sof(C28B)=Sof(H28B)=Sof(C29B)=Sof(H29B)=Sof(C30B)=Sof(H30B)=Sof(C31B)=
 Sof(H31B)=Sof(C32B)=Sof(H32B)=Sof(C33B)=Sof(H33B)=1-FVAR(1)
 Sof(C28A)=Sof(H28A)=Sof(C29A)=Sof(H29A)=Sof(C30A)=Sof(H30A)=Sof(C31A)=
 Sof(H31A)=Sof(C32A)=Sof(H32A)=Sof(C33A)=Sof(H33A)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C13(H13), C17(H17)
4.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)
4.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C28B(H28B), C29B(H29B), C30B(H30B),
 C31B(H31B), C32B(H32B), C33B(H33B), C28A(H28A), C29A(H29A), C30A(H30A),
 C31A(H31A), C32A(H32A), C33A(H33A), C22(H22), C23(H23), C24(H24), C25(H25),
 C26(H26), C27(H27)
4.d Fitted hexagon refined as free rotating group:
 C28B(C29B,C30B,C31B,C32B,C33B), C28A(C29A,C30A,C31A,C32A,C33A)
4.e Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
4.f Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              77168
_olex2_submission_special_instructions 'No special instructions were received'