Insertion of Alkylidene Carbenes into B-H Bonds.
Yang, Ji-Min; Guo, Feng-Kai; Zhao, Yu-Tao; Zhang, Qiao; Huang, Ming-Yao; Li, Mao-Lin; Zhu, Shou-Fei; Zhou, Qi-Lin; Journal of the American Chemical Society  (2020) –; doi:10.1021/jacs.0c09596

data_4135378
_publ_section_title
;
 Insertion of Alkylidene Carbenes into B-H Bonds.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.0c09596
_journal_year                    2020
_chemical_formula_moiety         'C18 H21 B F N'
_chemical_formula_sum            'C18 H21 B F N'
_chemical_formula_weight         281.17
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-20
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.2727(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.84648(7)
_cell_length_b                   6.18222(5)
_cell_length_c                   21.52570(12)
_cell_measurement_reflns_used    11901
_cell_measurement_temperature    294.15
_cell_measurement_theta_max      79.1690
_cell_measurement_theta_min      3.7420
_cell_volume                     1576.472(18)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      294.15
_diffrn_detector                 PILT
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.975
_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    -84.00  94.00   0.50    0.50    --    5.00  -7.00-127.00  356
  2  \w   -140.00  39.00   0.50    0.50    --  -50.10  -7.00-127.00  358
  3  \w   -199.00 -21.00   0.50    0.50    -- -110.00  -7.00-127.00  356
  4  \w   -199.00 -21.00   0.50    0.50    -- -110.00   7.00  49.00  356
  5  \w    -80.00  39.00   0.50    0.50    --  -50.10  57.00  90.00  238
  6  \w    -80.00  39.00   0.50    0.50    --  -50.10  57.00   0.00  238
  7  \w    -80.00  39.00   0.50    0.50    --  -50.10  57.00-180.00  238
  8  \w   -199.00 -77.00   0.50    0.50    -- -110.00 -72.00  74.24  244
  9  \w   -199.00 -78.00   0.50    0.50    -- -110.00 -69.00  20.12  242
 10  \w   -199.00 -77.00   0.50    0.50    -- -110.00 -72.00   6.98  244
 11  \w   -158.00 -92.00   0.50    0.50    -- -110.00 -45.00  47.62  132
 12  \w   -105.00 -67.00   0.50    0.50    -- -110.00  72.00-120.00   76
 13  \w   -143.00 -46.00   0.50    0.50    -- -110.00  72.00 150.00  194
 14  \w   -136.00 -61.00   0.50    0.50    -- -110.00  72.00-150.00  150
 15  \w   -169.00-143.00   0.50    0.50    -- -110.00 -57.00  90.00   52
 16  \w   -199.00 -99.00   0.50    0.50    -- -110.00 -38.00 -60.00  200
 17  \w   -141.00 -21.00   0.50    0.50    -- -110.00  38.00  60.00  240
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0708345000
_diffrn_orient_matrix_UB_12      -0.0179018000
_diffrn_orient_matrix_UB_13      -0.0595948000
_diffrn_orient_matrix_UB_21      -0.1084611000
_diffrn_orient_matrix_UB_22      0.0142670000
_diffrn_orient_matrix_UB_23      -0.0395643000
_diffrn_orient_matrix_UB_31      0.0113714000
_diffrn_orient_matrix_UB_32      0.2481761000
_diffrn_orient_matrix_UB_33      -0.0020307000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            19103
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.361
_diffrn_reflns_theta_min         3.731
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.595
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65065
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.134
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.0161(10)
_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   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3323
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0413
_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^)+(0.0584P)^2^+0.2152P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1148
_refine_ls_wR_factor_ref         0.1167
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3085
_reflns_number_total             3323
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c09596_si_002.cif
_cod_data_source_block           p20190320a
_cod_original_cell_volume        1576.471(18)
_cod_database_code               4135378
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C18H21BFN
_shelx_estimated_absorpt_t_max   0.880
_shelx_estimated_absorpt_t_min   0.814
_reflns_odcompleteness_completeness 98.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C9(H9), C10(H10), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_shelx_res_checksum              88933
_shelx_hkl_checksum              1845
_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 1.522
_oxdiff_exptl_absorpt_empirical_full_min 0.630