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_7129093
_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           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-07
_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                 95.838(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.6433(3)
_cell_length_b                   20.3069(3)
_cell_length_c                   18.5103(3)
_cell_measurement_reflns_used    4462
_cell_measurement_temperature    173(3)
_cell_measurement_theta_max      72.8970
_cell_measurement_theta_min      3.9380
_cell_volume                     6597.49(18)
_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(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4115
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.945
_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    -70.00  -1.00   1.00   11.59    --  -42.11  19.00-150.00   69
  2  \w    -27.00  69.00   1.00   11.59    --   42.11 -57.00   0.00   96
  3  \w     82.00 158.00   1.00   61.65    --  105.13 125.00  60.00   76
  4  \w     51.00 131.00   1.00   61.65    --  105.13 -45.00  60.00   80
  5  \w     51.00 106.00   1.00   61.65    --  105.13 -95.00 -90.00   55
  6  \w     42.00 109.00   1.00   61.65    --  105.13 -95.00  60.00   67
  7  \w     29.00 119.00   1.00   61.65    --  105.13 -30.00 150.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0603638000
_diffrn_orient_matrix_UB_12      -0.0551255000
_diffrn_orient_matrix_UB_13      0.0064209000
_diffrn_orient_matrix_UB_21      -0.0635887000
_diffrn_orient_matrix_UB_22      -0.0520760000
_diffrn_orient_matrix_UB_23      -0.0111692000
_diffrn_orient_matrix_UB_31      0.0041894000
_diffrn_orient_matrix_UB_32      0.0027143000
_diffrn_orient_matrix_UB_33      -0.0826435000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10961
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.345
_diffrn_reflns_theta_min         3.328
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.744
_exptl_absorpt_correction_T_max  0.931
_exptl_absorpt_correction_T_min  0.879
_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    1.113
_exptl_crystal_description       block
_exptl_crystal_F_000             2400
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: heptane'
_exptl_crystal_size_max          0.238
_exptl_crystal_size_mid          0.196
_exptl_crystal_size_min          0.126
_refine_diff_density_max         0.634
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         6280
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0490
_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^)+(0.0753P)^2^+3.3150P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1325
_refine_ls_wR_factor_ref         0.1438
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5107
_reflns_number_total             6280
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc05408b3.cif
_cod_data_source_block           10a
_cod_depositor_comments
'Adding full bibliography for 7129089--7129093.cif.'
_cod_database_code               7129093
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C36 H49 Al N2 O'
_chemical_oxdiff_usercomment     TH411
_reflns_odcompleteness_completeness 98.13
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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), C31(H31),
 C32(H32), C33(H33), C34(H34), C35(H35)
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), C37(H37A,H37B,H37C)
;
_shelx_res_checksum              90438
_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 1.105
_oxdiff_exptl_absorpt_empirical_full_min 0.901