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_7129090
_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         'C39 H55 Al N2 O3'
_chemical_formula_sum            'C39 H55 Al N2 O3'
_chemical_formula_weight         626.83
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-10-22
_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                82.674(5)
_cell_angle_beta                 80.349(5)
_cell_angle_gamma                88.508(5)
_cell_formula_units_Z            4
_cell_length_a                   14.1139(8)
_cell_length_b                   14.5855(9)
_cell_length_c                   18.1458(10)
_cell_measurement_reflns_used    5112
_cell_measurement_temperature    173.05(10)
_cell_measurement_theta_max      28.1190
_cell_measurement_theta_min      2.9570
_cell_volume                     3652.5(4)
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_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 0.986
_diffrn_measured_fraction_theta_max 0.790
_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    -39.00  51.00   1.00   12.13    --  -13.18  77.00  60.00   90
  2  \w    -80.00  12.00   1.00   12.13    --  -13.18 -77.00 -60.00   92
  3  \w     -2.00  82.00   1.00   12.13    --   14.27  57.00-150.00   84
;
_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      -0.0070048000
_diffrn_orient_matrix_UB_12      0.0334404000
_diffrn_orient_matrix_UB_13      -0.0306160000
_diffrn_orient_matrix_UB_21      0.0063461000
_diffrn_orient_matrix_UB_22      -0.0347513000
_diffrn_orient_matrix_UB_23      -0.0244318000
_diffrn_orient_matrix_UB_31      -0.0500934000
_diffrn_orient_matrix_UB_32      -0.0088410000
_diffrn_orient_matrix_UB_33      0.0079262000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0530
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.790
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            21313
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.790
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.346
_diffrn_reflns_theta_min         2.304
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.974
_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    1.140
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: heptane'
_exptl_crystal_size_max          0.516
_exptl_crystal_size_mid          0.288
_exptl_crystal_size_min          0.212
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     837
_refine_ls_number_reflns         14412
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0482
_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^)+(0.0618P)^2^+0.7461P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1172
_refine_ls_wR_factor_ref         0.1320
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10530
_reflns_number_total             14412
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc05408b3.cif
_cod_data_source_block           11d
_cod_depositor_comments
'Adding full bibliography for 7129089--7129093.cif.'
_cod_database_code               7129090
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C39H55AlN2O3
_chemical_oxdiff_usercomment     TH516
_reflns_odcompleteness_completeness 99.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_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 Ternary CH refined with riding coordinates:
 C12(H12), C15(H15), C24(H24), C27(H27), C62(H62), C65(H65), C74(H74), C77(H77)
2.b Secondary CH2 refined with riding coordinates:
 C30(H30A,H30B), C80(H80A,H80B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C8(H8), C9(H9), C10(H10), C20(H20), C21(H21), C22(H22), C32(H32),
 C35(H35), C36(H36), C52(H52), C58(H58), C59(H59), C60(H60), C70(H70), C71(H71),
  C72(H72), C82(H82), C85(H85), C86(H86)
2.d 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), C38(H38A,H38B,H38C), C40(H40A,
 H40B,H40C), C42(H42A,H42B,H42C), C54(H54A,H54B,H54C), C55(H55A,H55B,H55C),
 C63(H63A,H63B,H63C), C64(H64A,H64B,H64C), C66(H66A,H66B,H66C), C67(H67A,H67B,
 H67C), C75(H75A,H75B,H75C), C76(H76A,H76B,H76C), C78(H78A,H78B,H78C), C79(H79A,
 H79B,H79C), C88(H88A,H88B,H88C), C90(H90A,H90B,H90C), C92(H92A,H92B,H92C)
;
_shelx_res_checksum              75715
_olex2_date_sample_data_collection 2019-10-22
_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 1.042
_oxdiff_exptl_absorpt_empirical_full_min 0.850