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_1557970
_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         'C42 H42 Li2 N4 O2'
_chemical_formula_sum            'C42 H42 Li2 N4 O2'
_chemical_formula_weight         648.67
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-03-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-03-03 deposited with the CCDC.	2020-04-30 downloaded from the CCDC.
;
_cell_angle_alpha                105.659(2)
_cell_angle_beta                 94.8850(10)
_cell_angle_gamma                95.340(2)
_cell_formula_units_Z            1
_cell_length_a                   9.5878(2)
_cell_length_b                   9.9347(2)
_cell_length_c                   9.9435(2)
_cell_measurement_reflns_used    8515
_cell_measurement_temperature    173.01(10)
_cell_measurement_theta_max      76.5010
_cell_measurement_theta_min      4.6420
_cell_volume                     902.00(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.54a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.54a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.54a (Rigaku OD, 2020)'
_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_temperature      173.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.977
_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    -31.00  56.00   0.50    0.10    --  -18.75  29.00  40.00  174
  2  \w     36.00 122.00   0.50    0.10    --   47.95  29.00  40.00  172
  3  \w    -26.00  31.00   0.50    0.10    --   47.95 -29.00-120.00  114
  4  \w     95.00 171.00   0.50    0.30    --  107.11  29.00  40.00  152
  5  \w    -92.00  -6.00   0.50    0.10    --  -18.75 -29.00-120.00  172
  6  \w    -23.00  71.00   0.50    0.10    --   47.95 -77.00 -30.00  188
  7  \w    -26.00  23.00   0.50    0.10    --   47.95 -19.00 -60.00   98
  8  \w    -26.00  23.00   0.50    0.10    --   47.95 -19.00  60.00   98
  9  \w    -26.00  23.00   0.50    0.10    --   47.95 -19.00-180.00   98
 10  \w    -25.00  40.00   0.50    0.10    --   47.95 -38.00-150.00  130
 11  \w     35.00  96.00   0.50    0.10    --   47.95-125.00 120.00  122
 12  \w     35.00  68.00   0.50    0.30    --  107.11 -61.00-180.00   66
 13  \w     94.00 171.00   0.50    0.30    --  107.11  15.00-150.00  154
 14  \w     35.00 106.00   0.50    0.30    --  107.11 -94.00 120.00  142
 15  \w     35.00 106.00   0.50    0.30    --  107.11 -94.00 -30.00  142
 16  \w     35.00 106.00   0.50    0.30    --  107.11 -94.00-120.00  142
 17  \w     94.00 171.00   0.50    0.30    --  107.11  15.00 120.00  154
 18  \w     95.00 171.00   0.50    0.30    --  107.11 125.00 -90.00  152
 19  \w     35.00  68.00   0.50    0.30    --  107.11 -61.00-150.00   66
 20  \w     95.00 171.00   0.50    0.30    --  107.11  30.00  60.00  152
 21  \w     35.00  68.00   0.50    0.30    --  107.11 -61.00 -60.00   66
 22  \w     35.00 106.00   0.50    0.30    --  107.11 -94.00   0.00  142
 23  \w     35.00 102.00   0.50    0.30    --  107.11 -77.00 120.00  134
 24  \w     95.00 171.00   0.50    0.30    --  107.11  45.00 150.00  152
 25  \w     35.00 112.00   0.50    0.30    --  107.11-125.00 -30.00  154
 26  \w     35.00 112.00   0.50    0.30    --  107.11-125.00  30.00  154
 27  \w     35.00  68.00   0.50    0.30    --  107.11 -61.00 150.00   66
 28  \w     35.00 106.00   0.50    0.30    --  107.11 -94.00  90.00  142
 29  \w     95.00 171.00   0.50    0.30    --  107.11 125.00-180.00  152
 30  \w     35.00 106.00   0.50    0.30    --  107.11 -94.00-180.00  142
 31  \w     95.00 171.00   0.50    0.30    --  107.11  45.00 -60.00  152
 32  \w     35.00  68.00   0.50    0.30    --  107.11 -61.00  30.00   66
 33  \w     35.00  68.00   0.50    0.30    --  107.11 -61.00-120.00   66
 34  \w     26.00 120.00   0.50    0.10    --   47.95  77.00 -90.00  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13770
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.951
_diffrn_reflns_theta_min         4.649
_exptl_absorpt_coefficient_mu    0.567
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.54a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_description       plate
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3722
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0393
_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^)+(0.0523P)^2^+0.1719P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1120
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3222
_reflns_number_total             3722
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc01349h2.cif
_cod_data_source_block           20eh038_lb-lia-6
_cod_depositor_comments
;Adding full bibliography for 1557967--1557970.cif.

 Adding full bibliography for 1557967--1557970.cif.
;
_cod_database_code               1557970
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.895
_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 Aromatic/amide H refined with riding coordinates:
 C6(H6), C15(H15), C2(H2), C5(H5), C12(H12), C4(H4), C8(H8), C3(H3), C19(H19),
 C11(H11), C16(H16), C9(H9), C10(H10), C18(H18), C17(H17)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_shelx_res_checksum              37539
_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
;