Instability of Amide Bond with Trifluoroacetic Acid (20%): Synthesis, Conformational Analysis, and Mechanistic Insights into Cleavable Amide Bond Comprising β-Troponylhydrazino Acid.
Dalabehera, Nihar Ranjan; Meher, Sagarika; Bhusana Palai, Bibhuti; Sharma, Nagendra K.; ACS omega 5 (2020) 26141–26152; doi:10.1021/acsomega.0c03729

data_4518107
_publ_section_title
;
 Instability of Amide Bond with Trifluoroacetic Acid (20%): Synthesis,
 Conformational Analysis, and Mechanistic Insights into Cleavable Amide
 Bond Comprising \b-Troponylhydrazino Acid.
;
_journal_issue                   40
_journal_name_full               'ACS omega'
_journal_page_first              26141
_journal_page_last               26152
_journal_paper_doi               10.1021/acsomega.0c03729
_journal_volume                  5
_journal_year                    2020
_chemical_formula_moiety         'C18 H25 N3 O6'
_chemical_formula_sum            'C18 H24 N3 O6'
_chemical_formula_weight         378.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-08-23
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_cell_angle_alpha                90
_cell_angle_beta                 115.99(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.555(10)
_cell_length_b                   6.0271(13)
_cell_length_c                   28.976(13)
_cell_measurement_reflns_used    2318
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.5700
_cell_measurement_theta_min      3.4230
_cell_volume                     4169(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46b (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_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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     23.00  48.00   0.50   93.00    --    4.97-111.00 -16.00   50
  2  \w     -9.00  16.00   0.50   93.00    --   -5.44-111.00 -16.00   50
  3  \w     31.00  68.00   0.50   93.00    --    4.97  38.00 -60.00   74
  4  \w      7.00  33.00   0.50   93.00    --    4.97 -99.00 -60.00   52
  5  \w    -33.00   6.00   0.50   93.00    --    4.97 -38.00 -30.00   78
  6  \w    -58.00   3.00   0.50   93.00    --    4.97 -38.00 -60.00  122
  7  \w    -20.00  21.00   0.50   93.00    --   -5.44 -99.00-180.00   82
  8  \w    -69.00  -2.00   0.50   93.00    --   -5.44 -38.00  30.00  134
  9  \w     33.00  58.00   0.50   93.00    --   -5.44  57.00-180.00   50
 10  \w    -14.00  20.00   0.50   93.00    --   -5.44  57.00-180.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0252043000
_diffrn_orient_matrix_UB_12      -0.0141805000
_diffrn_orient_matrix_UB_13      0.0227731000
_diffrn_orient_matrix_UB_21      -0.0158535000
_diffrn_orient_matrix_UB_22      -0.0246691000
_diffrn_orient_matrix_UB_23      0.0137099000
_diffrn_orient_matrix_UB_31      0.0002817000
_diffrn_orient_matrix_UB_32      -0.1139103000
_diffrn_orient_matrix_UB_33      -0.0058531000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0802
_diffrn_reflns_av_unetI/netI     0.0638
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            20924
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.414
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33210
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46b (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_description       needle
_exptl_crystal_F_000             1608
_exptl_crystal_size_max          0.215
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.012
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         4250
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.1017
_refine_ls_R_factor_gt           0.0617
_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^)+(0.0790P)^2^+2.0590P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1543
_refine_ls_wR_factor_ref         0.1731
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2749
_reflns_number_total             4250
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ao0c03729_si_002.cif
_cod_data_source_block           nks_nrd_144
_cod_depositor_comments
'Adding full bibliography for 4518104--4518107.cif.'
_cod_original_cell_volume        4168(3)
_cod_database_code               4518107
_shelx_shelxl_version_number     2016/4
_chemical_oxdiff_formula         'C75 H75 N75 O75 '
_diffrn_oxdiff_ac3_digest_frames
;
01616691e2da6952b016f479ec1524e5df007603704
;
_diffrn_oxdiff_ac3_digest_hkl
;
0178039ee6b8b9e3aa57a1d32f76680a75548e
;
_reflns_odcompleteness_completeness 99.31
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.04
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C13(H13A,H13B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N007(H007), C5(H5), C2(H2A), C4(H4), C3(H3)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C18(H18A,H18B,
 H18C)
;
_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 2.822
_oxdiff_exptl_absorpt_empirical_full_min 0.555