Aluminum-Catalyzed Selective Hydroboration of Nitriles and Alkynes: A Multifunctional Catalyst.
Sarkar, Nabin; Bera, Subhadeep; Nembenna, Sharanappa; The Journal of organic chemistry 85 (2020) 4999–5009; doi:10.1021/acs.joc.0c00234

data_4038079
_publ_section_title
;
 Aluminum-Catalyzed Selective Hydroboration of Nitriles and Alkynes: A
 Multifunctional Catalyst.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4999
_journal_page_last               5009
_journal_paper_doi               10.1021/acs.joc.0c00234
_journal_volume                  85
_journal_year                    2020
_chemical_formula_moiety         'C20 H33 B2 N O4'
_chemical_formula_sum            'C20 H33 B2 N O4'
_chemical_formula_weight         373.09
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-07-24
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.779(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.0036(3)
_cell_length_b                   24.1961(6)
_cell_length_c                   15.6222(4)
_cell_measurement_reflns_used    12736
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      77.0070
_cell_measurement_theta_min      4.2870
_cell_volume                     4320.6(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45g (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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.960
_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   -102.00 -52.00   0.50    0.50    --  -38.50-157.00  22.00  100
  2  \w   -107.00 -19.00   0.50    0.50    --  -38.50 157.00  57.00  176
  3  \w    -85.00   4.00   0.50    0.50    --  -38.50 118.00 -97.00  178
  4  \w     18.00  96.00   0.50    0.50    --   49.31-118.00 176.00  156
  5  \w     41.00 118.00   0.50    0.50    --   49.31-157.00  22.00  154
  6  \w     43.00 139.00   0.50    1.96    --  106.38-157.00  22.00  192
  7  \w     40.00 113.00   0.50    1.96    --  106.38-118.00 176.00  146
  8  \w     98.00 173.00   0.50    1.96    --  106.38 118.00 -97.00  150
  9  \w     73.00 166.00   0.50    1.96    --  106.38 157.00  57.00  186
 10  \w   -103.00 -15.00   0.50    0.50    --  -38.50 -77.00   0.00  176
 11  \w    -42.00  28.00   0.50    0.50    --  -38.50  37.00 -90.00  140
 12  \w     46.00 116.00   0.50    0.50    --   49.31  37.00   0.00  140
 13  \w     46.00 116.00   0.50    0.50    --   49.31  37.00 -60.00  140
 14  \w     38.00 110.00   0.50    1.96    --  106.38 -94.00-180.00  144
 15  \w     93.00 169.00   0.50    1.96    --  106.38  61.00 -30.00  152
 16  \w     44.00 120.00   0.50    1.96    --  106.38 -61.00 -30.00  152
 17  \w     93.00 169.00   0.50    1.96    --  106.38  61.00  60.00  152
 18  \w     38.00 115.00   0.50    1.96    --  106.38 -15.00   0.00  154
 19  \w     39.00 109.00   0.50    1.96    --  106.38 -94.00-150.00  140
 20  \w     45.00 109.00   0.50    1.96    --  106.38 -30.00 150.00  128
 21  \w    110.00 170.00   0.50    1.96    --  106.38  45.00   0.00  120
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0867949000
_diffrn_orient_matrix_UB_12      -0.0482013000
_diffrn_orient_matrix_UB_13      -0.0089725000
_diffrn_orient_matrix_UB_21      0.0940867000
_diffrn_orient_matrix_UB_22      -0.0408389000
_diffrn_orient_matrix_UB_23      -0.0091869000
_diffrn_orient_matrix_UB_31      0.0422420000
_diffrn_orient_matrix_UB_32      -0.0077443000
_diffrn_orient_matrix_UB_33      0.1027695000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0647
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18626
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.169
_diffrn_reflns_theta_min         3.654
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.609
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24808
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.45g (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.147
_exptl_crystal_description       block
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.438
_refine_diff_density_rms         0.139
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         4398
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0607
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1030P)^2^+1.3410P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1620
_refine_ls_wR_factor_ref         0.1688
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3899
_reflns_number_total             4398
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00234_si_003.cif
_cod_data_source_block           sn-ns-intrtmediate
_cod_depositor_comments
'Adding full bibliography for 4038079--4038080.cif.'
_cod_original_cell_volume        4320.63(19)
_cod_database_code               4038079
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C168 H264 B16 O32 '
_diffrn_oxdiff_ac3_digest_frames
;
01dd14db5cff1cd385aef35c3c735f5457000460b13
;
_diffrn_oxdiff_ac3_digest_hkl
;
01bc5e080bf82043238b97fca1a45e247ec83d
;
_reflns_odcompleteness_completeness 99.17
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C8(H8), C5(H5), C7(H7)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C14(H14A,H14B,
 H14C), C13(H13A,H13B,H13C), C20(H20A,H20B,H20C), C17(H17A,H17B,H17C), C19(H19A,
 H19B,H19C)
;
_shelx_res_checksum              23568
_shelx_hkl_checksum              79665
_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 11.626
_oxdiff_exptl_absorpt_empirical_full_min 0.381