#------------------------------------------------------------------------------
#$Date: 2020-11-04 03:17:54 +0200 (Wed, 04 Nov 2020) $
#$Revision: 258703 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/81/4518107.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4518107
loop_
_publ_author_name
'Dalabehera, Nihar Ranjan'
'Meher, Sagarika'
'Bhusana Palai, Bibhuti'
'Sharma, Nagendra K.'
_publ_section_title
;
 Instability of Amide Bond with Trifluoroacetic Acid (20%): Synthesis,
 Conformational Analysis, and Mechanistic Insights into Cleavable Amide
 Bond Comprising β-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  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω     23.00  48.00   0.50   93.00    --    4.97-111.00 -16.00   50
  2  ω     -9.00  16.00   0.50   93.00    --   -5.44-111.00 -16.00   50
  3  ω     31.00  68.00   0.50   93.00    --    4.97  38.00 -60.00   74
  4  ω      7.00  33.00   0.50   93.00    --    4.97 -99.00 -60.00   52
  5  ω    -33.00   6.00   0.50   93.00    --    4.97 -38.00 -30.00   78
  6  ω    -58.00   3.00   0.50   93.00    --    4.97 -38.00 -60.00  122
  7  ω    -20.00  21.00   0.50   93.00    --   -5.44 -99.00-180.00   82
  8  ω    -69.00  -2.00   0.50   93.00    --   -5.44 -38.00  30.00  134
  9  ω     33.00  58.00   0.50   93.00    --   -5.44  57.00-180.00   50
 10  ω    -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       'ω 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/[σ²(Fo²)+(0.0790P)²+2.0590P] where P=(Fo²+2Fc²)/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 > 2σ(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 '
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.43153(7) 1.1695(3) 0.44200(6) 0.0567(4) Uani 1 1 d . . . . .
O4 O 0.51374(8) 0.3608(3) 0.36262(8) 0.0663(5) Uani 1 1 d . . . . .
O2 O 0.37000(7) 0.9012(3) 0.39313(7) 0.0708(5) Uani 1 1 d . . . . .
N1 N 0.41373(8) 0.9485(3) 0.32310(7) 0.0481(5) Uani 1 1 d . . . . .
N2 N 0.43167(8) 1.0710(3) 0.36860(7) 0.0512(5) Uani 1 1 d . . . . .
H2 H 0.457889 1.167888 0.376211 0.061 Uiso 1 1 calc R . . . .
O1 O 0.39518(9) 0.7986(3) 0.22702(7) 0.0785(6) Uani 1 1 d . . . . .
N007 N 0.57208(9) 0.5054(3) 0.33292(9) 0.0645(6) Uani 1 1 d . . . . .
H007 H 0.581320 0.619644 0.320569 0.077 Uiso 1 1 calc R . . . .
C7 C 0.36954(9) 1.0289(3) 0.27955(8) 0.0417(5) Uani 1 1 d . . . . .
C8 C 0.40710(9) 1.0356(4) 0.40116(8) 0.0491(5) Uani 1 1 d . . . . .
C1 C 0.35722(11) 0.9123(4) 0.23029(9) 0.0531(6) Uani 1 1 d . . . . .
C15 C 0.52848(10) 0.5195(4) 0.34450(8) 0.0480(5) Uani 1 1 d . . . . .
C14 C 0.49945(9) 0.7424(4) 0.33483(9) 0.0508(6) Uani 1 1 d . . . . .
H14A H 0.497458 0.803754 0.303127 0.061 Uiso 1 1 calc R . . . .
H14B H 0.521599 0.842809 0.362470 0.061 Uiso 1 1 calc R . . . .
C6 C 0.34323(10) 1.2256(4) 0.28164(10) 0.0520(6) Uani 1 1 d . . . . .
C13 C 0.43998(9) 0.7283(4) 0.33105(9) 0.0493(5) Uani 1 1 d . . . . .
H13A H 0.417276 0.631940 0.302704 0.059 Uiso 1 1 calc R . . . .
H13B H 0.441636 0.663865 0.362358 0.059 Uiso 1 1 calc R . . . .
O6 O 0.66147(12) 0.0570(4) 0.40334(11) 0.1127(10) Uani 1 1 d . . . . .
C9 C 0.40870(12) 1.1903(4) 0.48076(9) 0.0626(7) Uani 1 1 d . . . . .
C5 C 0.29706(12) 1.3402(5) 0.24431(11) 0.0663(7) Uani 1 1 d . . . . .
H5 H 0.291082 1.480574 0.254309 0.080 Uiso 1 1 calc R . . . .
C2 C 0.30275(12) 0.9239(5) 0.18729(10) 0.0684(7) Uani 1 1 d . . . . .
H2A H 0.293739 0.801441 0.165617 0.082 Uiso 1 1 calc R . . . .
C16 C 0.60390(13) 0.3025(4) 0.34073(12) 0.0736(8) Uani 1 1 d . . . . .
H16A H 0.621661 0.301964 0.317755 0.088 Uiso 1 1 calc R . . . .
H16B H 0.578302 0.177605 0.331587 0.088 Uiso 1 1 calc R . . . .
O5 O 0.66841(14) 0.4120(6) 0.42624(14) 0.1392(12) Uani 1 1 d . . . . .
C4 C 0.26020(12) 1.2805(6) 0.19663(12) 0.0768(8) Uani 1 1 d . . . . .
H4 H 0.231486 1.379809 0.178437 0.092 Uiso 1 1 calc R . . . .
C12 C 0.41248(14) 0.9699(5) 0.50729(11) 0.0769(8) Uani 1 1 d . . . . .
H12A H 0.385915 0.867998 0.483604 0.115 Uiso 1 1 calc GR . . . .
H12B H 0.404324 0.991367 0.536149 0.115 Uiso 1 1 calc GR . . . .
H12C H 0.449614 0.910712 0.518930 0.115 Uiso 1 1 calc GR . . . .
C3 C 0.26131(12) 1.0845(6) 0.17233(11) 0.0807(9) Uani 1 1 d . . . . .
H3 H 0.229845 1.056519 0.141678 0.097 Uiso 1 1 calc R . . . .
C17 C 0.64819(16) 0.2712(6) 0.39483(16) 0.0846(10) Uani 1 1 d . . . . .
C10 C 0.34970(16) 1.2834(7) 0.45470(15) 0.1059(13) Uani 1 1 d . . . . .
H10A H 0.349355 1.412100 0.435029 0.159 Uiso 1 1 calc GR . . . .
H10B H 0.337533 1.323959 0.480241 0.159 Uiso 1 1 calc GR . . . .
H10C H 0.324892 1.173156 0.432330 0.159 Uiso 1 1 calc GR . . . .
C11 C 0.44953(18) 1.3544(5) 0.51901(12) 0.0958(11) Uani 1 1 d . . . . .
H11A H 0.486597 1.292668 0.533587 0.144 Uiso 1 1 calc GR . . . .
H11B H 0.438442 1.383393 0.545827 0.144 Uiso 1 1 calc GR . . . .
H11C H 0.449230 1.490520 0.501668 0.144 Uiso 1 1 calc GR . . . .
C18 C 0.7091(2) 0.0013(10) 0.4517(2) 0.169(3) Uani 1 1 d . . . . .
H18A H 0.742372 0.069275 0.452836 0.254 Uiso 1 1 calc GR . . . .
H18B H 0.713914 -0.156836 0.454274 0.254 Uiso 1 1 calc GR . . . .
H18C H 0.702555 0.054719 0.479763 0.254 Uiso 1 1 calc GR . . . .
H6 H 0.3628(11) 1.293(4) 0.3157(11) 0.062(7) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O3 C9 120.9(2) . . ?
N2 N1 C13 112.73(18) . . ?
C7 N1 N2 118.56(17) . . ?
C7 N1 C13 127.93(18) . . ?
N1 N2 H2 120.2 . . ?
C8 N2 N1 119.67(19) . . ?
C8 N2 H2 120.2 . . ?
C15 N007 H007 119.2 . . ?
C15 N007 C16 121.6(2) . . ?
C16 N007 H007 119.2 . . ?
N1 C7 C1 116.82(19) . . ?
N1 C7 C6 120.07(19) . . ?
C6 C7 C1 122.6(2) . . ?
O3 C8 N2 108.63(19) . . ?
O2 C8 O3 127.4(2) . . ?
O2 C8 N2 124.0(2) . . ?
O1 C1 C7 118.8(2) . . ?
O1 C1 C2 119.8(2) . . ?
C2 C1 C7 121.4(2) . . ?
O4 C15 N007 121.8(2) . . ?
O4 C15 C14 122.4(2) . . ?
N007 C15 C14 115.82(19) . . ?
C15 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C15 C14 C13 112.86(18) . . ?
H14A C14 H14B 107.8 . . ?
C13 C14 H14A 109.0 . . ?
C13 C14 H14B 109.0 . . ?
C7 C6 C5 132.0(2) . . ?
C7 C6 H6 109.9(15) . . ?
C5 C6 H6 118.1(15) . . ?
N1 C13 C14 111.30(18) . . ?
N1 C13 H13A 109.4 . . ?
N1 C13 H13B 109.4 . . ?
C14 C13 H13A 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C17 O6 C18 116.7(4) . . ?
O3 C9 C12 110.4(2) . . ?
O3 C9 C10 109.1(2) . . ?
O3 C9 C11 101.9(2) . . ?
C12 C9 C10 113.6(3) . . ?
C12 C9 C11 109.4(2) . . ?
C10 C9 C11 111.8(3) . . ?
C6 C5 H5 114.6 . . ?
C4 C5 C6 130.8(3) . . ?
C4 C5 H5 114.6 . . ?
C1 C2 H2A 114.2 . . ?
C3 C2 C1 131.6(3) . . ?
C3 C2 H2A 114.2 . . ?
N007 C16 H16A 108.8 . . ?
N007 C16 H16B 108.8 . . ?
N007 C16 C17 113.9(3) . . ?
H16A C16 H16B 107.7 . . ?
C17 C16 H16A 108.8 . . ?
C17 C16 H16B 108.8 . . ?
C5 C4 H4 117.2 . . ?
C5 C4 C3 125.7(3) . . ?
C3 C4 H4 117.2 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C2 C3 H3 115.5 . . ?
C4 C3 C2 129.0(3) . . ?
C4 C3 H3 115.5 . . ?
O6 C17 C16 109.7(4) . . ?
O5 C17 O6 123.8(4) . . ?
O5 C17 C16 126.5(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O6 C18 H18A 109.5 . . ?
O6 C18 H18B 109.5 . . ?
O6 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C8 1.341(3) . ?
O3 C9 1.497(3) . ?
O4 C15 1.235(3) . ?
O2 C8 1.217(3) . ?
N1 N2 1.400(3) . ?
N1 C7 1.381(3) . ?
N1 C13 1.470(3) . ?
N2 H2 0.8600 . ?
N2 C8 1.379(3) . ?
O1 C1 1.257(3) . ?
N007 H007 0.8600 . ?
N007 C15 1.342(3) . ?
N007 C16 1.447(3) . ?
C7 C1 1.493(3) . ?
C7 C6 1.391(3) . ?
C1 C2 1.439(4) . ?
C15 C14 1.513(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C13 1.537(3) . ?
C6 C5 1.410(4) . ?
C6 H6 0.98(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
O6 C17 1.333(4) . ?
O6 C18 1.457(6) . ?
C9 C12 1.516(4) . ?
C9 C10 1.517(4) . ?
C9 C11 1.526(5) . ?
C5 H5 0.9300 . ?
C5 C4 1.346(4) . ?
C2 H2A 0.9300 . ?
C2 C3 1.384(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.503(5) . ?
O5 C17 1.187(4) . ?
C4 H4 0.9300 . ?
C4 C3 1.382(5) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C3 H3 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
