Synthesis, Characterisation and Reactivity studies of Chiral β-Diketiminate-like Supported Aluminium Lewis Acid Complexes Towards Difficult Diels Alder Cycloadditions
Dissanayake, Deepamali; Forsyth, Craig M.; Vidovic, Dragoslav; Dalton Transactions  (2023) –; doi:10.1039/D3DT00206C

data_7712495
_publ_section_title
;
 Synthesis, Characterisation and Reactivity studies of Chiral
 \b-Diketiminate-like Supported Aluminium Lewis Acid Complexes Towards
 Difficult Diels Alder Cycloadditions
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D3DT00206C
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C28 H32 N2 O'
_chemical_formula_sum            'C28 H32 N2 O'
_chemical_formula_weight         412.55
_space_group_crystal_system      trigonal
_space_group_IT_number           152
_space_group_name_Hall           'P 31 2"'
_space_group_name_H-M_alt        'P 31 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2022-07-19
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-01-18 deposited with the CCDC.	2023-03-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   10.56220(10)
_cell_length_b                   10.56220(10)
_cell_length_c                   37.6815(3)
_cell_measurement_reflns_used    33705
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      79.1400
_cell_measurement_theta_min      4.8200
_cell_volume                     3640.55(6)
_computing_cell_refinement       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_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    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_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     91.00 178.00   0.50    0.90    --  113.25  77.00-120.00  174
  2  \w    100.00 178.00   0.50    0.90    --  113.25  15.00 -60.00  156
  3  \w    101.00 178.00   0.50    0.90    --  113.25  30.00  60.00  154
  4  \w    101.00 178.00   0.50    0.90    --  113.25  30.00 150.00  154
  5  \w   -122.00 -35.00   0.50    0.30    --  -47.74 -19.00   0.00  174
  6  \w   -120.00 -35.00   0.50    0.30    --  -47.74 -42.00 -71.00  170
  7  \w   -119.00 -25.00   0.50    0.30    --  -47.74 -77.00-150.00  188
  8  \w   -163.00 -73.00   0.50    0.90    --  -91.75 -67.00  34.00  180
  9  \w    -84.00 -19.00   0.50    0.90    --  -91.75 123.00 164.00  130
 10  \w   -119.00 -33.00   0.50    0.30    --  -47.74 -57.00 120.00  172
 11  \w   -163.00 -79.00   0.50    0.90    --  -91.75 -86.00 158.00  168
 12  \w   -119.00 -73.00   0.50    0.30    --  -47.74-125.00-180.00   92
 13  \w   -119.00 -57.00   0.50    0.30    --  -47.74-148.00 -78.00  124
 14  \w   -119.00 -73.00   0.50    0.30    --  -47.74-125.00 -60.00   92
 15  \w   -119.00 -73.00   0.50    0.30    --  -47.74-125.00 -30.00   92
 16  \w     39.00  66.00   0.50    0.90    --  113.25 -30.00  30.00   54
 17  \w     42.00  76.00   0.50    0.90    --  113.25 -45.00 -30.00   68
 18  \w     42.00  76.00   0.50    0.90    --  113.25 -45.00-150.00   68
 19  \w     42.00  76.00   0.50    0.90    --  113.25 -45.00  30.00   68
 20  \w     42.00  76.00   0.50    0.90    --  113.25 -45.00 120.00   68
 21  \w     42.00  76.00   0.50    0.90    --  113.25 -45.00 150.00   68
 22  \w     42.00  76.00   0.50    0.90    --  113.25 -45.00 -90.00   68
 23  \w     41.00  73.00   0.50    0.90    --  113.25 -42.00 -71.00   64
 24  \w     39.00  66.00   0.50    0.90    --  113.25 -30.00   0.00   54
 25  \w     39.00  66.00   0.50    0.90    --  113.25 -30.00 150.00   54
 26  \w     95.00 178.00   0.50    0.90    --  113.25 125.00   0.00  166
 27  \w     95.00 178.00   0.50    0.90    --  113.25 125.00 -30.00  166
 28  \w     39.00  66.00   0.50    0.90    --  113.25 -30.00-180.00   54
 29  \w     39.00  66.00   0.50    0.90    --  113.25 -30.00-150.00   54
 30  \w     39.00  66.00   0.50    0.90    --  113.25 -30.00  90.00   54
 31  \w     42.00 105.00   0.50    0.90    --  113.25 -90.00  56.00  126
 32  \w     42.00 106.00   0.50    0.90    --  113.25 -94.00 120.00  128
 33  \w     42.00 106.00   0.50    0.90    --  113.25 -94.00 -60.00  128
 34  \w     42.00 108.00   0.50    0.90    --  113.25-110.00 -93.00  132
 35  \w     34.00  95.00   0.50    0.30    --   47.74-125.00-150.00  122
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0260697000
_diffrn_orient_matrix_UB_12      -0.1141627000
_diffrn_orient_matrix_UB_13      0.0287735000
_diffrn_orient_matrix_UB_21      0.1259731000
_diffrn_orient_matrix_UB_22      0.1188541000
_diffrn_orient_matrix_UB_23      0.0221665000
_diffrn_orient_matrix_UB_31      -0.1086372000
_diffrn_orient_matrix_UB_32      0.0347501000
_diffrn_orient_matrix_UB_33      0.0187744000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0147
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       48
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            50580
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.768
_diffrn_reflns_theta_min         3.519
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.525
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70057
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.129
_exptl_crystal_description       block
_exptl_crystal_F_000             1332
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 2113 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(6)
_refine_ls_extinction_coef       0.00066(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         5263
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0340
_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^)+(0.0484P)^2^+0.7253P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0900
_reflns_Friedel_coverage         0.717
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                5151
_reflns_number_total             5263
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3dt00206c2.cif
_cod_data_source_block           dd_cla17h_auto
_cod_original_cell_volume        3640.55(7)
_cod_database_code               7712495
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_shelx_estimated_absorpt_t_max   0.949
_shelx_estimated_absorpt_t_min   0.710
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C16(H16), C15(H15), C2(H2), C12(H12), C24(H24), C23(H23), C14(H14),
 C5(H5), C13(H13), C3(H3), C22(H22), C4(H4)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C20(H20A,H20B,H20C), C28(H28A,H28B,H28C), C27(H27A,H27B,
 H27C)
;
_shelx_res_checksum              53341
_shelx_hkl_checksum              50659
_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 1.299
_oxdiff_exptl_absorpt_empirical_full_min 0.748