Base-promoted direct amidation of esters: beyond the current scope and practical applications
Slavchev, Ivaylo; Ward, Jas. S.; Rissanen, Kari; Dobrikov, Georgi M.; Simeonov, Svilen; RSC Advances 12 (2022) 20555–20562; doi:10.1039/D2RA03524C

data_7245205
_publ_section_title
;
 Base-promoted direct amidation of esters: beyond the current scope and
 practical applications
;
_journal_issue                   32
_journal_name_full               'RSC Advances'
_journal_page_first              20555
_journal_page_last               20562
_journal_paper_doi               10.1039/D2RA03524C
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C21 H19 N3 O'
_chemical_formula_sum            'C21 H19 N3 O'
_chemical_formula_weight         329.39
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-09-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-02-03 deposited with the CCDC.	2022-07-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.691(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7084(3)
_cell_length_b                   10.2040(5)
_cell_length_c                   19.0448(7)
_cell_measurement_reflns_used    2300
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      76.0290
_cell_measurement_theta_min      4.6420
_cell_volume                     1690.46(12)
_computing_cell_refinement       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_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      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.968
_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   -115.00 -17.00   1.00    2.50    --  -41.40 -37.00 150.00   98
  2  \w      1.00  62.00   1.00    2.50    --   41.40 -99.00  30.00   61
  3  \w     19.00  72.00   1.00    2.50    --   41.40 -99.00-180.00   53
  4  \w    116.00 176.00   1.00   10.00    --  112.00  61.00 120.00   60
  5  \w     31.00 105.00   1.00   10.00    --  112.00 -94.00  60.00   74
  6  \w     40.00 104.00   1.00   10.00    --  112.00-111.00  30.00   64
  7  \w    108.00 169.00   1.00   10.00    --  112.00 111.00 150.00   61
  8  \w     52.00 141.00   1.00   10.00    --  112.00 -61.00  90.00   89
  9  \w     85.00 175.00   1.00   10.00    --  112.00  30.00 -90.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1355132000
_diffrn_orient_matrix_UB_12      -0.0972464000
_diffrn_orient_matrix_UB_13      -0.0035554000
_diffrn_orient_matrix_UB_21      0.1093368000
_diffrn_orient_matrix_UB_22      -0.1116290000
_diffrn_orient_matrix_UB_23      0.0238582000
_diffrn_orient_matrix_UB_31      -0.0311755000
_diffrn_orient_matrix_UB_32      0.0298646000
_diffrn_orient_matrix_UB_33      0.0773777000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6340
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.683
_diffrn_reflns_theta_min         4.649
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.644
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.579
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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    1.294
_exptl_crystal_description       plate
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.192
_exptl_crystal_size_min          0.028
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3428
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0431
_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^)+(0.0564P)^2^+0.3244P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1178
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2754
_reflns_number_total             3428
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ra03524c2.cif
_cod_data_source_block           84
_cod_database_code               7245205
_shelxl_version_number           2014/6
_reflns_odcompleteness_completeness 98.84
_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 N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
2.b Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C)
;
_shelx_res_checksum              78490
_ins_header
;
TITL OHD113-2-CD068_auto in P2(1)/c 
REM P2(1)/c (#14 in standard setting)
CELL 1.54184   8.708372  10.204010  19.044763  90.0000  92.6911  90.0000
ZERR    4.00   0.000346   0.000464   0.000668   0.0000   0.0036   0.0000
LATT  1
SYMM -x, y+1/2,-z+1/2 
SFAC C H N O
UNIT 84.00 76.00 12.00 4.00
TREF
HKLF 4
END
;
_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 1.282
_oxdiff_exptl_absorpt_empirical_full_min 0.799