Catalyst Control of Selectivity in the C‒O Bond Alumination of Biomass Derived Furans
Hooper, Thomas; Brown, Ryan; Rekhroukh, Feriel; Garçon, Martí; White, Andrew J. P.; Costa, Paulo J.; Crimmin, Mark Richard; Chemical Science  (2020) –; doi:10.1039/D0SC01918F

data_1558544
_publ_section_title
;
 Catalyst Control of Selectivity in the C--O Bond Alumination of Biomass
 Derived Furans
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC01918F
_journal_year                    2020
_chemical_formula_moiety         'C33 H45 Al N2 O'
_chemical_formula_sum            'C33 H45 Al N2 O'
_chemical_formula_weight         512.69
_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             2018-12-20
_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.	2020-07-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.2427(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9108(2)
_cell_length_b                   12.4443(2)
_cell_length_c                   22.7523(4)
_cell_measurement_reflns_used    3227
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      73.1490
_cell_measurement_theta_min      3.9100
_cell_volume                     3049.14(9)
_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      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4115
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.946
_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    -97.00  -9.00   1.00    6.36    --  -42.36 125.00 -90.00   88
  2  \w     24.00 109.00   1.00    6.36    --   42.36  57.00 150.00   85
  3  \w     39.00 129.00   1.00   41.30    --  105.13 -61.00 150.00   90
  4  \w     39.00 121.00   1.00   41.30    --  105.13-125.00 120.00   82
  5  \w     87.00 175.00   1.00   41.30    --  105.13  45.00 -60.00   88
  6  \w     82.00 169.00   1.00   41.30    --  105.13 125.00 150.00   87
;
_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      0.0792228000
_diffrn_orient_matrix_UB_12      -0.0077641000
_diffrn_orient_matrix_UB_13      0.0623219000
_diffrn_orient_matrix_UB_21      -0.0016081000
_diffrn_orient_matrix_UB_22      0.1234574000
_diffrn_orient_matrix_UB_23      0.0054994000
_diffrn_orient_matrix_UB_31      -0.1190328000
_diffrn_orient_matrix_UB_32      -0.0066888000
_diffrn_orient_matrix_UB_33      0.0281107000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0628
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9780
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.494
_diffrn_reflns_theta_min         3.937
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.770
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_correction_T_min  0.903
_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    1.117
_exptl_crystal_description       block
_exptl_crystal_F_000             1112
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: heptane'
_exptl_crystal_size_max          0.177
_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.066
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         5819
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0450
_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^)+(0.0487P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1216
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4312
_reflns_number_total             5819
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc01918f3.cif
_cod_data_source_block           4a
_cod_original_cell_volume        3049.16(11)
_cod_database_code               1558544
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         C33H45AlN2O
_chemical_oxdiff_usercomment     TH393
_reflns_odcompleteness_completeness 98.78
_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), C30(H30),
 C31(H31), C32(H32), C33(H33)
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)
;
_shelx_res_checksum              89633
_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 1.097
_oxdiff_exptl_absorpt_empirical_full_min 0.941