Reaction of sterically encumbered phenols, TEMPO-H, and organocarbonyl insertion reactions with L-AlH2 (L = HC(MeCNDipp)2, Dipp = 2,6-diisopropylphenyl)
Keyes, Lauren K.; Todd, Angela D. K.; Giffin, Nick A.; Veinot, Alex J.; Hendsbee, Arthur D.; Robertson, Katherine N.; Geier, Stephen J.; Masuda, Jason D.; RSC Adv. 7 (2017) 37315–; doi:10.1039/C7RA06526D

data_7228787
_publ_section_title
;
 Reaction of sterically encumbered phenols, TEMPO-H, and organocarbonyl
 insertion reactions with L-AlH2 (L = HC(MeCNDipp)2, Dipp =
 2,6-diisopropylphenyl)
;
_journal_issue                   59
_journal_name_full               'RSC Adv.'
_journal_page_first              37315
_journal_paper_doi               10.1039/C7RA06526D
_journal_volume                  7
_journal_year                    2017
_chemical_formula_moiety         'C43 H55 Al N2 O2'
_chemical_formula_sum            'C43 H55 Al N2 O2'
_chemical_formula_weight         658.87
_chemical_name_systematic
;
 ? 
;
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-08-12
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2017-05-05 deposited with the CCDC.
2017-07-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.259(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.513(5)
_cell_length_b                   9.348(2)
_cell_length_c                   22.483(6)
_cell_measurement_reflns_used    6133
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.86
_cell_measurement_theta_min      2.20
_cell_volume                     3887.9(17)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            37041
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.084
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0948 before and 0.0484 after correction.
The Ratio of minimum to maximum transmission is 0.9236.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.126
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     510
_refine_ls_number_reflns         6839
_refine_ls_number_restraints     429
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0427
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0402P)^2^+1.9425P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.1095
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5021
_reflns_number_total             6839
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra06526d1.cif
_cod_data_source_block           lk08_0m
_cod_original_cell_volume        3887.7(17)
_cod_database_code               7228787
_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. Restrained distances
 C38B-C39B
 1.4 with sigma of 0.001
 C39B-C40B
 1.4 with sigma of 0.001
 C40B-C41B
 1.4 with sigma of 0.001
 C41B-C42B
 1.4 with sigma of 0.001
 C42B-C43B
 1.4 with sigma of 0.001
 C43B-C38B
 1.4 with sigma of 0.001
3. Restrained planarity
 C38B, C39B, C40B, C41B, C42B, C43B
 with sigma of 0.1
4. Rigid bond restraints
 C38B, C39B, C40B, C41B, C42B, C43B, C38, C39, C40, C41, C42, C43
 with sigma for 1-2 distances of 0.03 and sigma for 1-3 distances of 0.03
5. Uiso/Uaniso restraints and constraints
C38B \\sim C39B \\sim C40B \\sim C41B \\sim C42B \\sim C43B \\sim C38 \\sim C39
\\sim C40 \\sim C41 \\sim C42 \\sim C43: within 6A with sigma of 0.03 and sigma
for terminal atoms of 0.03
Uanis(O2) = Uanis(O2B)
6. Others
 Sof(O2B)=Sof(C37B)=Sof(H37C)=Sof(H37D)=Sof(C38B)=Sof(H38B)=Sof(C39B)=
 Sof(H39B)=Sof(C40B)=Sof(H40B)=Sof(C41B)=Sof(H41B)=Sof(C42B)=Sof(H42B)=
 Sof(C43B)=1-FVAR(1)
 Sof(O2)=Sof(C37)=Sof(H37A)=Sof(H37B)=Sof(C38)=Sof(C39)=Sof(H39)=Sof(C40)=
 Sof(H40)=Sof(C41)=Sof(H41)=Sof(C42)=Sof(H42)=Sof(C43)=Sof(H43)=FVAR(1)
7.a Ternary CH refined with riding coordinates:
 C12(H12), C15(H15), C24(H24), C27(H27)
7.b Secondary CH2 refined with riding coordinates:
 C30(H30A,H30B), C37(H37A,H37B), C37B(H37C,H37D)
7.c Aromatic/amide H refined with riding coordinates:
 C32(H32), C33(H33), C34(H34), C35(H35), C36(H36), C3(H3), C8(H8), C9(H9),
 C10(H10), C20(H20), C21(H21), C22(H22), C39(H39), C40(H40), C41(H41), C42(H42),
  C43(H43), C38B(H38B), C39B(H39B), C40B(H40B), C41B(H41B), C42B(H42B)
7.d Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), 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              18100
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'