Room temperature catalytic carbon-hydrogen bond alumination of unactivated arenes: mechanism and selectivity.
Hooper, Thomas N.; Garçon, Martí; White, Andrew J. P.; Crimmin, Mark R.; Chemical science 9 (2018) 5435–5440; doi:10.1039/c8sc02072h

data_1549476
_publ_section_title
;
 Room temperature catalytic carbon-hydrogen bond alumination of
 unactivated arenes: mechanism and selectivity.
;
_journal_issue                   24
_journal_name_full               'Chemical science'
_journal_page_first              5435
_journal_page_last               5440
_journal_paper_doi               10.1039/c8sc02072h
_journal_volume                  9
_journal_year                    2018
_chemical_formula_moiety         'C36 H48.90 Al Cl0.10 N2'
_chemical_formula_sum            'C36 H48.9 Al Cl0.1 N2'
_chemical_formula_weight         540.19
_chemical_name_systematic        Dipp-BDIAlH(o-tol)
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2018-03-13 deposited with the CCDC.
2018-05-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.077(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0860(4)
_cell_length_b                   22.1931(7)
_cell_length_c                   12.9055(4)
_cell_measurement_reflns_used    2772
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.0220
_cell_measurement_theta_min      2.5430
_cell_volume                     3326.2(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0382
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.812
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.812
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11620
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.812
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.215
_diffrn_reflns_theta_min         2.539
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.079
_exptl_crystal_description       block
_exptl_crystal_F_000             1174
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane'
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.172
_exptl_crystal_size_min          0.106
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     376
_refine_ls_number_reflns         6657
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0870
_refine_ls_R_factor_gt           0.0589
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0598P)^2^+1.5972P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1387
_refine_ls_wR_factor_ref         0.1540
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4878
_reflns_number_total             6657
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc02072h4.cif
_cod_data_source_block           4o
_cod_depositor_comments
'Adding full bibliography for 1549475--1549478.cif.'
_cod_original_formula_sum        'C36 H48.90 Al Cl0.10 N2'
_cod_database_code               1549476
_shelx_shelxl_version_number     2017/1
_oxdiff_exptl_absorpt_empirical_full_min 0.900
_oxdiff_exptl_absorpt_empirical_full_max 1.108
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_shelx_res_checksum              24512