Aluminum-catalyzed anti-Markovnikov hydroamination of aromatic alkenes with aromatic amines.
Yan, Wenliang; Ma, Xiaoli; Li, Qifeng; Pang, Ziyuan; Yang, Xiaobo; Chen, Yiwen; Yang, Zhi; Organic & biomolecular chemistry 23 (2025) 1347–1353; doi:10.1039/d4ob01820f

data_7160317
_publ_section_title
;
 Aluminum-catalyzed anti-Markovnikov hydroamination of aromatic alkenes
 with aromatic amines.
;
_journal_issue                   6
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1347
_journal_page_last               1353
_journal_paper_doi               10.1039/d4ob01820f
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C23 H31 Al N2 O4'
_chemical_formula_sum            'C23 H31 Al N2 O4'
_chemical_formula_weight         426.48
_chemical_name_systematic        Aea2
_space_group_crystal_system      orthorhombic
_space_group_IT_number           41
_space_group_name_Hall           'A 2 -2ab'
_space_group_name_H-M_alt        'A e a 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-11-05
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2024-11-11 deposited with the CCDC.	2024-12-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.4662(5)
_cell_length_b                   21.9361(7)
_cell_length_c                   15.0299(5)
_cell_measurement_reflns_used    6507
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.1730
_cell_measurement_theta_min      3.4040
_cell_volume                     4769.5(3)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.823
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.823
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14189
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.727
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.940
_diffrn_reflns_theta_min         3.261
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_type   none
_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    1.188
_exptl_crystal_description       block
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 1734 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         5505
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0549P)^2^+1.4108P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1054
_reflns_Friedel_coverage         0.706
_reflns_Friedel_fraction_full    0.924
_reflns_Friedel_fraction_max     0.624
_reflns_number_gt                4670
_reflns_number_total             5505
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01820f2.cif
_cod_data_source_block           111
_cod_depositor_comments          'Adding full bibliography for 7160317.cif.'
_cod_original_sg_symbol_Hall     'A 2 -2ac'
_cod_database_code               7160317
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.960
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00H(H00H), C00I(H00I), C00J(H00J), C00L(H00L), C00O(H00O),
 C00Q(H00S)
2.b Idealised Me refined as rotating group:
 C00K(H00B,H00C,H00D), C00M(H00E,H00F,H00G), C00N(H00K,H00M,H00N), C00P(H00P,
 H00Q,H00R), C00R(H00T,H00U,H00V), C00S(H00W,H00X,H00Y), C00T(H00Z,H,HA),
 C00U(H00,HB,HC)
;
_shelx_res_checksum              2945
_olex2_submission_special_instructions 'No special instructions were received'