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_7129171
_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         'C38 H30 B2 F15 N3 O, C6 H6'
_chemical_formula_sum            'C44 H36 B2 F15 N3 O'
_chemical_formula_weight         929.37
_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
_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                112.2910(10)
_cell_angle_beta                 98.8880(10)
_cell_angle_gamma                105.1620(10)
_cell_formula_units_Z            2
_cell_length_a                   11.13660(10)
_cell_length_b                   14.3079(2)
_cell_length_c                   14.5576(2)
_cell_measurement_reflns_used    27004
_cell_measurement_temperature    99.9(2)
_cell_measurement_theta_max      77.2440
_cell_measurement_theta_min      3.4210
_cell_volume                     1986.21(5)
_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      99.9(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 0.977
_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    -71.00  24.00   0.50    0.44    --  -48.41  76.00-174.00  190
  2  \w    -24.00  27.00   0.50    0.44    --  -48.41  19.00-180.00  102
  3  \w    -49.00 -14.00   0.50    1.76    --  -86.25  45.00 -30.00   70
  4  \w    -49.00 -14.00   0.50    1.76    --  -86.25  45.00  30.00   70
  5  \w    -49.00 -14.00   0.50    1.76    --  -86.25  45.00   0.00   70
  6  \w    -24.00  27.00   0.50    0.44    --  -48.41  19.00 120.00  102
  7  \w    -49.00 -14.00   0.50    1.76    --  -86.25  45.00 120.00   70
  8  \w   -120.00 -26.00   0.50    0.44    --  -48.41 -76.00  58.00  188
  9  \w   -120.00 -73.00   0.50    0.44    --  -48.41-125.00-120.00   94
 10  \w   -159.00 -64.00   0.50    1.76    --  -86.25 -76.00  58.00  190
 11  \w   -159.00 -83.00   0.50    1.76    --  -86.25 -94.00 120.00  152
 12  \w    -23.00  71.00   0.50    0.44    --   48.41 -76.00  58.00  188
 13  \w     35.00 104.00   0.50    1.76    --  107.75 -76.00  58.00  138
 14  \w     35.00 106.00   0.50    1.76    --  107.75 -94.00 -30.00  142
 15  \w     36.00 178.00   0.50    1.76    --  107.75   0.00  90.00  284
 16  \w     95.00 178.00   0.50    1.76    --  107.75  30.00 150.00  166
 17  \w     95.00 178.00   0.50    1.76    --  107.75 125.00  60.00  166
 18  \w     95.00 178.00   0.50    1.76    --  107.75 125.00 -90.00  166
 19  \w     95.00 178.00   0.50    1.76    --  107.75  45.00  60.00  166
 20  \w     91.00 178.00   0.50    1.76    --  107.75  61.00 -90.00  174
 21  \w     85.00 178.00   0.50    1.76    --  107.75  76.00-174.00  186
 22  \w     35.00 106.00   0.50    1.76    --  107.75 -94.00  90.00  142
 23  \w     35.00 106.00   0.50    1.76    --  107.75 -94.00 -60.00  142
 24  \w     35.00 106.00   0.50    1.76    --  107.75 -94.00-180.00  142
 25  \w     35.00  73.00   0.50    1.76    --  107.75 -61.00 -30.00   76
 26  \w     35.00 107.00   0.50    1.76    --  107.75 -77.00 -30.00  144
 27  \w     35.00 112.00   0.50    1.76    --  107.75-125.00  60.00  154
 28  \w     35.00 106.00   0.50    1.76    --  107.75 -94.00 120.00  142
 29  \w     35.00 106.00   0.50    1.76    --  107.75 -98.00  48.06  142
 30  \w     35.00 106.00   0.50    1.76    --  107.75 -94.00 150.00  142
 31  \w     35.00  73.00   0.50    1.76    --  107.75 -61.00  60.00   76
 32  \w     35.00 106.00   0.50    1.76    --  107.75 -94.00-120.00  142
 33  \w     35.00 106.00   0.50    1.76    --  107.75 -94.00-150.00  142
 34  \w     35.00  73.00   0.50    1.76    --  107.75 -61.00-150.00   76
 35  \w     26.00 121.00   0.50    0.44    --   48.41  76.00-174.00  190
 36  \w     26.00  98.00   0.50    0.44    --   48.41  77.00 -60.00  144
 37  \w    -26.00  28.00   0.50    0.44    --   48.41 -19.00 -60.00  108
 38  \w   -100.00 -13.00   0.50    1.76    --  -86.25  76.00-174.00  174
;
_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      -0.0854241000
_diffrn_orient_matrix_UB_12      -0.0543492000
_diffrn_orient_matrix_UB_13      0.0522409000
_diffrn_orient_matrix_UB_21      -0.0176022000
_diffrn_orient_matrix_UB_22      -0.1117145000
_diffrn_orient_matrix_UB_23      -0.0843185000
_diffrn_orient_matrix_UB_31      0.1213986000
_diffrn_orient_matrix_UB_32      -0.0008662000
_diffrn_orient_matrix_UB_33      0.0662634000
_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  0.0381
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            38258
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.546
_diffrn_reflns_theta_min         3.422
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.244
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.585
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (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    1.554
_exptl_crystal_description       prism
_exptl_crystal_F_000             948
_exptl_crystal_recrystallization_method 'Slow evaporation from benzene'
_exptl_crystal_size_max          0.178
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.046
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.00098(13)
_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   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     591
_refine_ls_number_reflns         8258
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0336
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0391P)^2^+0.7935P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0887
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7332
_reflns_number_total             8258
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc05673e2.cif
_cod_data_source_block           10
_cod_depositor_comments
;

2025-03-31
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C88 H72 B4 F30 N6 O2'
_cod_original_formula_weight         1858.75
_cod_original_formula_moiety         '2(C38 H30 B2 F15 N3 O), 2(C6 H6)'
_cod_original_formula_units_Z            1
_cod_database_code               7129171
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C88  H72  B4  F30  N6  O2  '
_reflns_odcompleteness_completeness 99.89
_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), C39(H39), C40(H40), C41(H41), C42(H42),
 C43(H43), C44(H44)
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              91249
_olex2_date_sample_data_collection 2020-12-01
_olex2_date_sample_submission    2020-12-01
_olex2_exptl_crystal_mounting_method 'MiTeGen 50 um MicroLoop'
_olex2_submission_original_sample_id kre20_38
_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 1.431
_oxdiff_exptl_absorpt_empirical_full_min 0.745