Highly selective catalytic trans-hydroboration of alkynes mediated by borenium cations and B(C6F5)3
McGough, John S.; Butler, Samuel M.; Cade, Ian A.; Ingleson, Michael J.; Chem. Sci. 7 (2016) 3384–; doi:10.1039/C5SC04798F

data_1542433
_publ_section_title
;
 Highly selective catalytic trans-hydroboration of alkynes mediated by
 borenium cations and B(C6F5)3
;
_journal_issue                   5
_journal_name_full               'Chem. Sci.'
_journal_page_first              3384
_journal_paper_doi               10.1039/C5SC04798F
_journal_volume                  7
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C36 H27 B2 Cl4 F15 N4'
_chemical_formula_sum            'C36 H27 B2 Cl4 F15 N4'
_chemical_formula_weight         964.04
_chemical_name_systematic        '[9-BBN(I-DCDM)2][HBCF]'
_chemical_properties_physical    Moisture-sensitive
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_update_record
;
2015-10-28 deposited with the CCDC.
2016-02-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.728(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.8757(6)
_cell_length_b                   20.3411(11)
_cell_length_c                   10.7976(7)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     1908.7(2)
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies,'
_computing_data_collection       'CrysAlisPro, Agilent Technologies,'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies,'
_computing_molecular_graphics    'Ortep3 v. 2.02 (LJ Farrugia, 1997)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 8.0714
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measurement_details
;
  1 omega  -79.00  -40.00   1.0000   77.3600
omega____ theta____ kappa____ phi______ frames
    -      -20.7110 -178.0000 -180.0000 39

  2 omega   -2.00   85.00   1.0000   77.3600
omega____ theta____ kappa____ phi______ frames
    -       21.3360   57.0000  150.0000 87

  3 omega  -47.00   52.00   1.0000   77.3600
omega____ theta____ kappa____ phi______ frames
    -       21.3360  -77.0000    0.0000 99
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.026
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8992
_diffrn_reflns_theta_full        26.260
_diffrn_reflns_theta_max         29.127
_diffrn_reflns_theta_min         3.374
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.420
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72395
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec  3 2012,18:21:49)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.54
_refine_diff_density_min         -0.55
_refine_ls_abs_structure_details 'Flack (1983), 2509 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9775
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     551
_refine_ls_number_reflns         7014
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0528
_refine_ls_shift/su_max          0.0003049
_refine_ls_shift/su_mean         0.0000598
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.02P)^2^ + 0.40P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0879
_refine_ls_wR_factor_gt          0.0785
_refine_ls_wR_factor_ref         0.0879
_reflns_limit_h_max              11
_reflns_limit_h_min              -12
_reflns_limit_k_max              26
_reflns_limit_k_min              -25
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                5444
_reflns_number_total             7031
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.45
_oxford_diffrn_Wilson_scale      0.02
_oxford_refine_ls_r_factor_ref   0.0725
_oxford_refine_ls_scale          7.70(11)
_oxford_reflns_number_all        7014
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_iucr_refine_instructions_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE B   (   2,X'S) H   (  27,X'S) 
RIDE C   (   1,X'S) H   (   1,X'S) 
RIDE C   (   2,X'S) H   (   3,X'S) H   (   2,X'S) 
RIDE C   (   3,X'S) H   (   4,X'S) H   (   5,X'S) 
RIDE C   (   4,X'S) H   (   6,X'S) H   (   7,X'S) 
RIDE C   (   5,X'S) H   (   8,X'S) 
RIDE C   (   6,X'S) H   (   9,X'S) H   (  10,X'S) 
RIDE C   (   7,X'S) H   (  11,X'S) H   (  12,X'S) 
RIDE C   (   8,X'S) H   (  13,X'S) H   (  14,X'S) 
RIDE C   (  10,X'S) H   (  16,X'S) H   (  17,X'S) H   (  15,X'S) 
RIDE C   (  13,X'S) H   (  19,X'S) H   (  18,X'S) H   (  20,X'S) 
RIDE C   (  15,X'S) H   (  22,X'S) H   (  23,X'S) H   (  21,X'S) 
RIDE C   (  18,X'S) H   (  24,X'S) H   (  26,X'S) H   (  25,X'S) 
END                                                                             
;
_iucr_refine_instructions_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_cod_data_source_file            c5sc04798f2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
 Removing duplicate rows from the ATOM_TYPE loop.

 Antanas Vaitkus,
 2018-08-10

 Adding full bibliography for 1542431--1542434.cif.
;
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_database_code               1542433