Ultrafast amidation of esters using lithium amides under aerobic ambient temperature conditions in sustainable solvents.
Fairley, Michael; Bole, Leonie J.; Mulks, Florian F.; Main, Laura; Kennedy, Alan R.; O'Hara, Charles T; García-Alvarez, Joaquín; Hevia, Eva; Chemical science 11 (2020) 6500–6509; doi:10.1039/d0sc01349h

data_1557968
_publ_section_title
;
 Ultrafast amidation of esters using lithium amides under aerobic ambient
 temperature conditions in sustainable solvents.
;
_journal_issue                   25
_journal_name_full               'Chemical science'
_journal_page_first              6500
_journal_page_last               6509
_journal_paper_doi               10.1039/d0sc01349h
_journal_volume                  11
_journal_year                    2020
_chemical_formula_moiety         'C30 H36 Li2 N6 O2'
_chemical_formula_sum            'C30 H36 Li2 N6 O2'
_chemical_formula_weight         526.53
_chemical_properties_physical
Air-sensitive,Moisture-sensitive,Oxygen-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-06-13
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Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
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_audit_update_record
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2019-12-20 deposited with the CCDC.	2020-04-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.012(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.7406(4)
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_cell_length_c                   14.1465(7)
_cell_measurement_reflns_used    2891
_cell_measurement_temperature    123.35(10)
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_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_diffrn_ambient_environment      N~2~
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 13 omega   53.00   93.00   1.0000    3.5000
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 17 omega   48.00   93.00   1.0000    3.5000
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 18 omega   42.00  107.00   1.0000    3.5000
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 19 omega   50.00  135.00   1.0000    3.5000
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 31 omega  137.00  175.00   1.0000    3.5000
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 32 omega   93.00  147.00   1.0000    3.5000
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 33 omega   61.00   87.00   1.0000    3.5000
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;
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_diffrn_radiation_monochromator  graphite
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_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
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_diffrn_source                   'Enhance (Cu) X-ray Source'
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_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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_exptl_crystal_colour            colourless
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_refine_ls_structure_factor_coef Fsqd
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'w=1/[\s^2^(Fo^2^)+(0.1022P)^2^+0.1093P] where P=(Fo^2^+2Fc^2^)/3'
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_cod_data_source_file            d0sc01349h2.cif
_cod_data_source_block           mf-3a
_cod_depositor_comments
;Adding full bibliography for 1557967--1557970.cif.

 Adding full bibliography for 1557967--1557970.cif.
;
_cod_database_code               1557968
_shelx_shelxl_version_number     2017/1
_reflns_odcompleteness_completeness 99.73
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O1-C12 = O1-C15 = O2-C20 = O2-C17
 1.43 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C18) = Uanis(C14)
Uanis(O1) = Uanis(O2)
4. Others
 Sof(O2)=Sof(C18)=Sof(H18A)=Sof(H18B)=Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(H21C)=
 Sof(C17)=Sof(H17)=Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(C19)=Sof(H19A)=Sof(H19B)=1-
 FVAR(1)
 Sof(O1)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(C15)=
 Sof(H15)=Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(H16C)=Sof(C14)=Sof(H14A)=Sof(H14B)=
 FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C17(H17), C15(H15)
5.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C20(H20A,H20B), C19(H19A,H19B), C13(H13A,H13B), C12(H12A,
 H12B), C14(H14A,H14B)
5.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C8(H8), C7(H7), C9(H9), C10(H10)
5.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              13692
_olex2_submission_special_instructions 'No special instructions were received'