Catalytic B-H Bond Insertion Reactions Using Alkynes as Carbene Precursors.
Yang, Ji-Min; Li, Zi-Qi; Li, Mao-Lin; He, Qiao; Zhu, Shou-Fei; Zhou, Qi-Lin; Journal of the American Chemical Society  (2017) –; doi:10.1021/jacs.6b13168

data_4125601
_publ_section_title
;
 Catalytic B-H Bond Insertion Reactions Using Alkynes as Carbene
 Precursors.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.6b13168
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H24 B N O2'
_chemical_formula_sum            'C17 H24 B N O2'
_chemical_formula_weight         285.18
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-09-20
_audit_creation_method
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.48052(10)
_cell_length_b                   9.63870(12)
_cell_length_c                   27.4697(3)
_cell_measurement_reflns_used    10835
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      78.5310
_cell_measurement_theta_min      3.2170
_cell_volume                     1715.86(4)
_computing_cell_refinement
;
CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)
;
_computing_data_reduction
;
CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 PILT
_diffrn_detector_area_resol_mean 5.814
_diffrn_detector_type            'Rigaku Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.985
_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    -50.00  40.00   1.00    5.00    --  -35.00  72.00-180.00   90
  2  \w   -123.00 -33.00   1.00    5.00    --  -35.00 -72.00-108.00   90
  3  \w    -50.00  40.00   1.00    5.00    --  -35.00  72.00-108.00   90
  4  \w    -50.00  40.00   1.00    5.00    --  -35.00  43.00-108.00   90
  5  \w   -200.00 -96.00   1.00    5.00    -- -110.00 -72.00   0.00  104
  6  \w   -114.00 -20.00   1.00    5.00    -- -110.00  72.00-108.00   94
  7  \w   -200.00-110.00   1.00    5.00    -- -110.00 -15.00-108.00   90
  8  \w   -125.00 -32.00   1.00    5.00    -- -110.00  72.00  72.00   93
  9  \w   -125.00 -32.00   1.00    5.00    -- -110.00  43.00  36.00   93
 10  \w   -123.00 -33.00   1.00    5.00    -- -110.00  72.00-180.00   90
 11  \w   -187.00 -97.00   1.00    5.00    -- -110.00 -72.00  36.00   90
 12  \w   -117.00 -27.00   1.00    5.00    -- -110.00  72.00 -72.00   90
 13  \w   -125.00 -33.00   1.00    5.00    -- -110.00  72.00-144.00   92
 14  \w   -115.00 -25.00   1.00    5.00    -- -110.00  43.00-180.00   90
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku XtaLab P200'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support Fiber
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0368588000
_diffrn_orient_matrix_UB_12      -0.0262920000
_diffrn_orient_matrix_UB_13      -0.0546258000
_diffrn_orient_matrix_UB_21      -0.2344834000
_diffrn_orient_matrix_UB_22      0.0048862000
_diffrn_orient_matrix_UB_23      -0.0090857000
_diffrn_orient_matrix_UB_31      0.0134478000
_diffrn_orient_matrix_UB_32      0.1575681000
_diffrn_orient_matrix_UB_33      -0.0088619000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0173
_diffrn_reflns_av_unetI/netI     0.0118
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            14160
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.291
_diffrn_reflns_theta_min         3.218
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_target            Cu
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           40.0
_exptl_absorpt_coefficient_mu    0.552
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
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    1.104
_exptl_crystal_description       prism
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1438 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(5)
_refine_ls_extinction_coef       0.0263(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         3633
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0368
_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^)+(0.0740P)^2^+0.0780P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1065
_reflns_Friedel_coverage         0.699
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.962
_reflns_number_gt                3547
_reflns_number_total             3633
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b13168_si_002.cif
_cod_data_source_block           p20160919a
_cod_database_code               4125601
_chemical_oxdiff_formula         C17H2BNO2
_shelx_estimated_absorpt_t_max   0.907
_shelx_estimated_absorpt_t_min   0.843
_reflns_odcompleteness_completeness 98.32
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     79.04
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C7(H7A,H7B,H7C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C),
 C17(H17A,H17B,H17C)
;
_shelx_res_checksum              24313
_shelx_hkl_checksum              2994
_shelx_shelxl_version_number     2014/7
_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 1.312
_oxdiff_exptl_absorpt_empirical_full_min 0.752