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_4038080
_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         'C42 H55 Al N5'
_chemical_formula_sum            'C42 H55 Al N5'
_chemical_formula_weight         656.89
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-04-11
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.7533(6)
_cell_length_b                   20.3581(9)
_cell_length_c                   28.1812(12)
_cell_measurement_reflns_used    9029
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      21.783
_cell_measurement_theta_min      2.168
_cell_volume                     9037.9(7)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_unetI/netI     0.0386
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            62435
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.425
_diffrn_reflns_theta_min         1.445
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6722
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0900 before and 0.0511 after correction. The Ratio of minimum to maximum transmission is 0.9020. The \l/2 correction factor is 0.00150.'
_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    0.966
_exptl_crystal_description       block
_exptl_crystal_F_000             2840
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.698
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     413
_refine_ls_number_reflns         8286
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.1481
_refine_ls_R_factor_gt           0.0917
_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^)+(0.2200P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2864
_refine_ls_wR_factor_ref         0.3450
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4258
_reflns_number_total             8286
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00234_si_002.cif
_cod_data_source_block           sn_sb_115_1r_om
_cod_depositor_comments
'Adding full bibliography for 4038079--4038080.cif.'
_cod_database_code               4038080
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H30A,H30B,H30C} of C30, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  {H12A,H12B,H12C} of C12, {H40A,H40B,H40C} of C40, {H32A,H32B,H32C} of C32,
  {H10A,H10B,H10C} of C10, {H20A,H20B,H20C} of C20, {H42A,H42B,H42C} of C42,
  {H22A,H22B,H22C} of C22
2. Uiso/Uaniso restraints and constraints
Uanis(C10) = Uanis(C20) = Uanis(C22) = Uanis(C40) = Uanis(C32) = Uanis(C30) =
Uanis(C42)
3.a Secondary CH2 refined with riding coordinates:
 C41(H41A,H41B), C29(H29A,H29B), C11(H11A,H11B), C19(H19A,H19B), C21(H21A,
 H21B), C31(H31A,H31B), C39(H39A,H39B)
3.b Aromatic/amide H refined with riding coordinates:
 N4(H4), N5(H5), C37(H37), C25(H25), C35(H35), C15(H15), C36(H36), C5(H5A),
 C17(H17), C16(H16), C6(H6), C27(H27), C26(H26), C7(H7), C9(H9)
3.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C40(H40A,H40B,H40C), C20(H20A,H20B,H20C), C42(H42A,H42B,
 H42C), C22(H22A,H22B,H22C), C32(H32A,H32B,H32C), C10(H10A,H10B,H10C), C30(H30A,
 H30B,H30C)
;
_olex2_submission_special_instructions 'No special instructions were received'