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_1542431
_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_compound_source        'University of Manchester'
_chemical_formula_moiety         'C18 H B F15, C15 H26 B N2'
_chemical_formula_sum            'C33 H27 B2 F15 N2'
_chemical_formula_weight         758.19
_chemical_name_systematic        '[9-BBN(i-DCDM)][HBCF]'
_chemical_properties_physical    'Air-sensitive, Moisture-sensitive'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_update_record
;
2015-10-28 deposited with the CCDC.
2016-02-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 117.953(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3052(10)
_cell_length_b                   33.5364(19)
_cell_length_c                   10.5825(11)
_cell_measurement_reflns_used    3322
_cell_measurement_temperature    151(2)
_cell_measurement_theta_max      26.3520
_cell_measurement_theta_min      3.3310
_cell_volume                     3230.6(6)
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies (2013)'
_computing_data_collection       'CrysAlisPro, Agilent Technologies (2013)'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies (2013)'
_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      151(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.872
_diffrn_measurement_details
;
  1 omega  -54.00   21.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.3942   57.0000   60.0000 75

  2 omega   -7.00   27.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.3942  -99.0000   30.0000 34

  3 omega  -68.00   49.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.3942   19.0000  -90.0000 117

  4 omega   86.00  116.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       25.8629  178.0000   30.0000 30

;
_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     0.71073
_diffrn_reflns_av_R_equivalents  0.032
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13188
_diffrn_reflns_theta_full        26.320
_diffrn_reflns_theta_max         28.516
_diffrn_reflns_theta_min         3.264
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41179
_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    1.559
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1536.008
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.56
_refine_diff_density_min         -0.45
_refine_ls_extinction_coef       200(30)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0269
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     771
_refine_ls_number_reflns         7143
_refine_ls_number_restraints     228
_refine_ls_R_factor_all          0.0985
_refine_ls_R_factor_gt           0.0717
_refine_ls_shift/su_max          0.0005265
_refine_ls_shift/su_mean         0.0000389
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.02P)^2^ + 8.22P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1613
_refine_ls_wR_factor_gt          0.1491
_refine_ls_wR_factor_ref         0.1613
_reflns_limit_h_max              12
_reflns_limit_h_min              -13
_reflns_limit_k_max              43
_reflns_limit_k_min              0
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                5196
_reflns_number_total             7156
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.95
_oxford_diffrn_Wilson_scale      0.21
_oxford_refine_ls_r_factor_ref   0.0985
_oxford_refine_ls_scale          2.59(3)
_oxford_reflns_number_all        7143
_oxford_reflns_threshold_expression_ref I>0.0\s(I)
_cod_data_source_file            c5sc04798f2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_primary' value 'Other' changed to 'other'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 1542431--1542434.cif.
;
_cod_original_sg_symbol_H-M      'P 21/n '
_cod_database_code               1542431
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S F(20, U'S, OCC) UNTIL C(181) 
CONT C(200, U'S) UNTIL C(215) 
CONT B(10, U'S, OCC) UNTIL B(11) 
CONT N(1, U'S) UNTIL N(2) 
CONT EXTPARAM 
EQUIV F(20, OCC), F(21, OCC), F(30, OCC), F(31, OCC) 
CONT F(40, OCC), F(41, OCC), F(50, OCC), F(51, OCC) 
CONT F(60, OCC), F(61, OCC), F(80, OCC), F(81, OCC) 
CONT F(90, OCC), F(91, OCC), F(100, OCC), F(101, OCC) 
CONT F(110, OCC), F(111, OCC), F(120, OCC), F(121, OCC) 
CONT F(140, OCC), F(141, OCC), F(150, OCC), F(151, OCC) 
CONT F(160, OCC), F(161, OCC), F(170, OCC), F(171, OCC) 
CONT F(180, OCC), F(181, OCC), C(10, OCC), C(11, OCC) 
CONT C(20, OCC), C(21, OCC), C(30, OCC), C(31, OCC) 
CONT C(40, OCC), C(41, OCC), C(50, OCC), C(51, OCC) 
CONT C(60, OCC), C(61, OCC), C(70, OCC), C(71, OCC) 
CONT C(80, OCC), C(81, OCC), C(90, OCC), C(91, OCC) 
CONT C(100, OCC), C(101, OCC), C(110, OCC), C(111, OCC) 
CONT C(120, OCC), C(121, OCC), C(130, OCC), C(131, OCC) 
CONT C(140, OCC), C(141, OCC), C(150, OCC), C(151, OCC) 
CONT C(160, OCC), C(161, OCC), C(170, OCC), C(171, OCC) 
CONT C(180, OCC), C(181, OCC), B(10, OCC), B(11, OCC) 
WEIGHT -1 F(21, OCC), F(31, OCC), F(41, OCC), F(51, OCC) 
CONT F(61, OCC), F(81, OCC), F(91, OCC), F(101, OCC) 
CONT F(111, OCC), F(121, OCC), F(141, OCC), F(151, OCC) 
CONT F(161, OCC), F(171, OCC), F(181, OCC), C(11, OCC) 
CONT C(21, OCC), C(31, OCC) C(41, OCC), C(51, OCC) 
CONT C(61, OCC), C(71, OCC), C(81, OCC), C(91, OCC) 
CONT C(101, OCC), C(111, OCC), C(121, OCC), C(131, OCC) 
CONT C(141, OCC), C(151, OCC), C(161, OCC), C(171, OCC), C(181, OCC) 
CONT B(11, OCC) 
RIDE B   (  10,X'S) H   (   1,X'S) 
RIDE B   (  11,X'S) H   (   2,X'S) 
RIDE C   ( 201,X'S) H   (2011,X'S) H   (2012,X'S) H   (2013,X'S) 
RIDE C   ( 203,X'S) H   (2031,X'S) H   (2032,X'S) H   (2033,X'S) 
RIDE C   ( 205,X'S) H   (2051,X'S) H   (2052,X'S) H   (2053,X'S) 
RIDE C   ( 206,X'S) H   (2061,X'S) H   (2062,X'S) H   (2063,X'S) 
RIDE C   ( 208,X'S) H   (2081,X'S) 
RIDE C   ( 209,X'S) H   (2091,X'S) H   (2092,X'S) 
RIDE C   ( 210,X'S) H   (2101,X'S) H   (2102,X'S) 
RIDE C   ( 211,X'S) H   (2111,X'S) H   (2112,X'S) 
RIDE C   ( 212,X'S) H   (2121,X'S) 
RIDE C   ( 213,X'S) H   (2131,X'S) H   (2132,X'S) 
RIDE C   ( 214,X'S) H   (2141,X'S) H   (2142,X'S) 
RIDE C   ( 215,X'S) H   (2151,X'S) H   (2152,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
DIST 0.0, 0.01 = MEAN C(20) TO F(20), C(21) TO F(21) 
DIST 0.0, 0.01 = MEAN C(30) TO F(30), C(31) TO F(31) 
DIST 0.0, 0.01 = MEAN C(40) TO F(40), C(41) TO F(41) 
DIST 0.0, 0.01 = MEAN C(50) TO F(50), C(51) TO F(51) 
DIST 0.0, 0.01 = MEAN C(60) TO F(60), C(61) TO F(61) 
REM 
DIST 0.0, 0.01 = MEAN C(80) TO F(80), C(81) TO F(81) 
DIST 0.0, 0.01 = MEAN C(90) TO F(90), C(91) TO F(91) 
DIST 0.0, 0.01 = MEAN C(100) TO F(100), C(101) TO F(101) 
DIST 0.0, 0.01 = MEAN C(110) TO F(110), C(111) TO F(111) 
DIST 0.0, 0.01 = MEAN C(120) TO F(120), C(121) TO F(121) 
REM 
DIST 0.0, 0.01 = MEAN C(140) TO F(140), C(141) TO F(141) 
DIST 0.0, 0.01 = MEAN C(150) TO F(150), C(151) TO F(151) 
DIST 0.0, 0.01 = MEAN C(160) TO F(160), C(161) TO F(161) 
DIST 0.0, 0.01 = MEAN C(170) TO F(170), C(171) TO F(171) 
DIST 0.0, 0.01 = MEAN C(180) TO F(180), C(181) TO F(181) 
REM 
U(IJ) 0.0, 0.02 = C(10) TO C(11) 
U(IJ) 0.0, 0.02 = C(20) TO C(21) 
U(IJ) 0.0, 0.02 = C(30) TO C(31) 
U(IJ) 0.0, 0.01 = C(40) TO C(41) 
U(IJ) 0.0, 0.01 = C(50) TO C(51) 
U(IJ) 0.0, 0.02 = C(60) TO C(61) 
U(IJ) 0.0, 0.02 = C(70) TO C(71) 
U(IJ) 0.0, 0.02 = C(80) TO C(81) 
U(IJ) 0.0, 0.02 = C(90) TO C(91) 
U(IJ) 0.0, 0.01 = C(100) TO C(101) 
U(IJ) 0.0, 0.02 = C(110) TO C(111) 
U(IJ) 0.0, 0.02 = C(120) TO C(121) 
U(IJ) 0.0, 0.02 = C(130) TO C(131) 
U(IJ) 0.0, 0.02 = C(140) TO C(141) 
U(IJ) 0.0, 0.01 = C(150) TO C(151) 
U(IJ) 0.0, 0.01 = C(160) TO C(161) 
U(IJ) 0.0, 0.01 = C(170) TO C(171) 
U(IJ) 0.0, 0.02 = C(180) TO C(181) 
REM 
U(IJ) 0.0, 0.02 = F(20) TO F(21) 
U(IJ) 0.0, 0.02 = F(30) TO F(31) 
U(IJ) 0.0, 0.02 = F(40) TO F(41) 
U(IJ) 0.0, 0.02 = F(50) TO F(51) 
U(IJ) 0.0, 0.02 = F(60) TO F(61) 
U(IJ) 0.0, 0.02 = F(80) TO F(81) 
U(IJ) 0.0, 0.02 = F(90) TO F(91) 
U(IJ) 0.0, 0.02 = F(100) TO F(101) 
U(IJ) 0.0, 0.02 = F(110) TO F(111) 
U(IJ) 0.0, 0.02 = F(120) TO F(121) 
U(IJ) 0.0, 0.02 = F(140) TO F(141) 
U(IJ) 0.0, 0.02 = F(150) TO F(151) 
U(IJ) 0.0, 0.02 = F(160) TO F(161) 
U(IJ) 0.0, 0.02 = F(170) TO F(171) 
U(IJ) 0.0, 0.02 = F(180) TO F(181) 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;