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_4518105
_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         'C10 H10 N2 O2'
_chemical_formula_sum            'C10 H10 N2 O2'
_chemical_formula_weight         190.20
_chemical_name_systematic        NRD_50
_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_Int_Tables_number      14
_atom_sites_solution_primary     dual
_audit_creation_date             2018-09-26
_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                 105.389(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7164(4)
_cell_length_b                   12.3920(4)
_cell_length_c                   7.6809(3)
_cell_measurement_reflns_used    4519
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.7080
_cell_measurement_theta_min      4.6930
_cell_volume                     891.67(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.9725
_diffrn_measured_fraction_theta_max 0.9725
_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   -104.00 -35.00   0.50    1.00    --  -38.50 -39.00-161.00  138
  2  \w    -42.00  28.00   0.50    1.00    --  -38.50  39.00  -7.00  140
  3  \w    -17.00  53.00   0.50    1.00    --   49.06 -39.00-161.00  140
  4  \w     46.00 115.00   0.50    1.00    --   49.06  39.00  -7.00  138
  5  \w    103.00 172.00   0.50    5.37    --  106.38  39.00  -7.00  138
  6  \w     41.00 110.00   0.50    5.37    --  106.38 -39.00-161.00  138
  7  \w    -50.00  24.00   0.50    1.00    --  -38.50  57.00 120.00  148
  8  \w    -17.00  52.00   0.50    1.00    --   49.06 -37.00  60.00  138
  9  \w    102.00 171.00   0.50    5.37    --  106.38  45.00-120.00  138
 10  \w     94.00 171.00   0.50    5.37    --  106.38 125.00-120.00  154
 11  \w    102.00 171.00   0.50    5.37    --  106.38  45.00  30.00  138
 12  \w    102.00 171.00   0.50    5.37    --  106.38  45.00 -90.00  138
 13  \w     42.00 111.00   0.50    5.37    --  106.38 -45.00 -90.00  138
 14  \w     38.00 109.00   0.50    5.37    --  106.38 -94.00-180.00  142
 15  \w     42.00 111.00   0.50    5.37    --  106.38 -45.00  30.00  138
 16  \w     44.00 120.00   0.50    5.37    --  106.38 -61.00 -60.00  152
 17  \w     42.00 111.00   0.50    5.37    --  106.38 -45.00   0.00  138
 18  \w     26.00 114.00   0.50    1.00    --   49.06  77.00 120.00  176
;
_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      -0.1433790000
_diffrn_orient_matrix_UB_12      0.0075850000
_diffrn_orient_matrix_UB_13      0.0494680000
_diffrn_orient_matrix_UB_21      -0.0738753000
_diffrn_orient_matrix_UB_22      -0.0617977000
_diffrn_orient_matrix_UB_23      -0.1736279000
_diffrn_orient_matrix_UB_31      0.0324532000
_diffrn_orient_matrix_UB_32      -0.1075706000
_diffrn_orient_matrix_UB_33      0.1032780000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1030
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6532
_diffrn_reflns_theta_full        76.9379
_diffrn_reflns_theta_max         76.94
_diffrn_reflns_theta_min         4.72
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.834
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.21212
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic light brown'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.4167
_exptl_crystal_description       needle
_exptl_crystal_F_000             401.3667
_exptl_crystal_size_max          0.001
_exptl_crystal_size_mid          0.0001
_exptl_crystal_size_min          0.0001
_refine_diff_density_max         0.3699
_refine_diff_density_min         -0.3353
_refine_diff_density_rms         0.1074
_refine_ls_d_res_high            0.7914
_refine_ls_d_res_low             9.3680
_refine_ls_goodness_of_fit_ref   1.0341
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    18
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1838
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0341
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0805
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1933P)^2^+0.1420P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2538
_refine_ls_wR_factor_ref         0.2620
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -12
_reflns_limit_k_max              15
_reflns_limit_k_min              0
_reflns_limit_l_max              9
_reflns_limit_l_min              0
_reflns_number_gt                1563
_reflns_number_total             1838
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            ao0c03729_si_005.cif
_cod_data_source_block           NKS_NRD_50
_cod_depositor_comments
'Adding full bibliography for 4518104--4518107.cif.'
_cod_database_code               4518105
_chemical_oxdiff_formula         'C40 H44 N8 O8 '
_diffrn_oxdiff_ac3_digest_frames
;
010f2a114b57894baacfeb4c8401ccec93000302c45
;
_diffrn_oxdiff_ac3_digest_hkl
;
01a32e233132e66de7aa9bb378eba7df618ee8
;
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C009(H00a,H00b), C00A(H00c,H00d)
2.b Aromatic/amide H refined with riding coordinates:
 N004(H004), C007(H007), C00B(H00e), C00C(H00f), C00D(H00g), C00E(H00h)
;
_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 4.785
_oxdiff_exptl_absorpt_empirical_full_min 0.151