Alumination of aryl methyl ethers: switching between sp<sup>2</sup> and sp<sup>3</sup> C-O bond functionalisation with Pd-catalysis.
Brown, Ryan K.; Hooper, Thomas N.; Rekhroukh, Feriel; White, Andrew J. P.; Costa, Paulo J.; Crimmin, Mark R.; Chemical communications (Cambridge, England) 57 (2021) 11673–11676; doi:10.1039/d1cc05408b

data_7129089
_publ_section_title
;
 Alumination of aryl methyl ethers: switching between sp<sup>2</sup> and
 sp<sup>3</sup> C-O bond functionalisation with Pd-catalysis.
;
_journal_issue                   88
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              11673
_journal_page_last               11676
_journal_paper_doi               10.1039/d1cc05408b
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C36 H49 Al N2 O'
_chemical_formula_sum            'C36 H49 Al N2 O'
_chemical_formula_weight         552.75
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-12-19 deposited with the CCDC.	2021-10-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.380(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1329(4)
_cell_length_b                   36.3892(15)
_cell_length_c                   10.2426(4)
_cell_measurement_reflns_used    3114
_cell_measurement_temperature    173.05(10)
_cell_measurement_theta_max      27.0570
_cell_measurement_theta_min      3.0590
_cell_volume                     3382.9(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_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0382
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.797
_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    -30.00  50.00   1.00    4.96    --  -13.18  57.00-120.00   80
  2  \w    -78.00   4.00   1.00    4.96    --  -13.18 -37.00  60.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0517224000
_diffrn_orient_matrix_UB_12      -0.0120237000
_diffrn_orient_matrix_UB_13      0.0346343000
_diffrn_orient_matrix_UB_21      0.0161350000
_diffrn_orient_matrix_UB_22      0.0135801000
_diffrn_orient_matrix_UB_23      0.0491460000
_diffrn_orient_matrix_UB_31      -0.0563175000
_diffrn_orient_matrix_UB_32      -0.0071457000
_diffrn_orient_matrix_UB_33      0.0351951000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0763
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.797
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -46
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11733
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.797
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.364
_diffrn_reflns_theta_min         2.508
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.972
_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_colour_primary    colourless
_exptl_crystal_density_diffrn    1.085
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: heptane'
_exptl_crystal_size_max          0.605
_exptl_crystal_size_mid          0.348
_exptl_crystal_size_min          0.256
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         6749
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0905
_refine_ls_R_factor_gt           0.0633
_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^)+(0.0633P)^2^+0.7177P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1424
_refine_ls_wR_factor_ref         0.1620
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5004
_reflns_number_total             6749
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc05408b3.cif
_cod_data_source_block           9a
_cod_depositor_comments
'Adding full bibliography for 7129089--7129093.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7129089
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C36H49AlN2O
_chemical_oxdiff_usercomment     TH481
_reflns_odcompleteness_completeness 98.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_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 Ternary CH refined with riding coordinates:
 C12(H12), C15(H15), C24(H24), C27(H27)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C8(H8), C9(H9), C10(H10), C20(H20), C21(H21), C22(H22), C33(H33),
 C34(H34), C35(H35), C36(H36), C37(H37)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C),
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C25(H25A,H25B,H25C), C26(H26A,H26B,
 H26C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C)
;
_shelx_res_checksum              57299
_olex2_date_sample_data_collection 2019-09-04
_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 1.056
_oxdiff_exptl_absorpt_empirical_full_min 0.935