New Amino acid, Hybrid Peptides and BODIPY Analogs: Synthesis and Evaluation of 2-Aminotroponyl-L-Alanine (ATA) Derivatives
Sharma, Nagendra K.; Gupta, Manish Kumar; Organic & Biomolecular Chemistry  (2022) –; doi:10.1039/D2OB01905A

data_7158980
_publ_section_title
;
 New Amino acid, Hybrid Peptides and BODIPY Analogs: Synthesis and
 Evaluation of 2-Aminotroponyl-L-Alanine (ATA) Derivatives
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01905A
_journal_year                    2022
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C10 H13 N2 O3, C2 F3 O2'
_chemical_formula_sum            'C12 H13 F3 N2 O5'
_chemical_formula_weight         322.243
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_Int_Tables_number      1
_atom_sites_solution_primary     dual
_audit_creation_date             2022-05-25
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-05-25 deposited with the CCDC.	2022-11-11 downloaded from the CCDC.
;
_cell_angle_alpha                76.575(4)
_cell_angle_beta                 80.995(5)
_cell_angle_gamma                77.331(4)
_cell_formula_units_Z            1
_cell_length_a                   4.9797(3)
_cell_length_b                   6.2209(3)
_cell_length_c                   11.7288(6)
_cell_measurement_reflns_used    6456
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31.2340
_cell_measurement_theta_min      3.5280
_cell_volume                     342.66(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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.9992
_diffrn_measured_fraction_theta_max 0.8749
_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    -29.00  38.00   0.50   24.00    --    6.83 -91.00-112.00  134
  2  \w    -29.00  24.00   0.50   24.00    --   -7.14 -91.00-112.00  106
  3  \w    -38.00   8.00   0.50   24.00    --   -7.14  91.00   1.00   92
  4  \w      1.00  76.00   0.50   24.00    --    6.83  19.00  60.00  150
  5  \w    -61.00  13.00   0.50   24.00    --    6.83 -19.00  90.00  148
  6  \w      4.00  73.00   0.50   24.00    --    6.83  38.00 120.00  138
  7  \w     -9.00  50.00   0.50   24.00    --    6.83-111.00 176.63  118
  8  \w      1.00  76.00   0.50   24.00    --    6.83  19.00 -60.00  150
  9  \w      4.00  73.00   0.50   24.00    --    6.83  38.00-180.00  138
 10  \w    -59.00  10.00   0.50   24.00    --    6.83 -38.00 -30.00  138
 11  \w     -5.00  70.00   0.50   24.00    --    6.83  57.00  60.00  150
 12  \w    -70.00   4.00   0.50   24.00    --   -7.14 -57.00-180.00  148
 13  \w    -68.00 -33.00   0.50   24.00    --   -7.14 141.00  97.62   70
 14  \w    -59.00 -24.00   0.50   24.00    --   -7.14 126.00-135.18   70
 15  \w    -75.00 -36.00   0.50   24.00    --   -7.14 150.00-129.34   78
 16  \w    -20.00  29.00   0.50   24.00    --   -7.14 -99.00-120.00   98
 17  \w    -61.00 -27.00   0.50   24.00    --   -7.14 129.00  -8.08   68
 18  \w    -60.00 -26.00   0.50   24.00    --   -7.14 128.00 -45.63   68
 19  \w    -71.00  16.00   0.50   24.00    --   -7.14 -77.00  60.00  174
 20  \w    -63.00 -29.00   0.50   24.00    --   -7.14 133.00 175.22   68
 21  \w    -62.00 -27.00   0.50   24.00    --   -7.14 131.00  33.77   70
 22  \w      4.00  73.00   0.50   24.00    --    6.83  38.00-150.00  138
 23  \w    -58.00 -28.00   0.50   24.00    --   -7.14 125.00 148.68   60
;
_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      -0.1108291000
_diffrn_orient_matrix_UB_12      0.0055929000
_diffrn_orient_matrix_UB_13      -0.0325687000
_diffrn_orient_matrix_UB_21      -0.0568159000
_diffrn_orient_matrix_UB_22      -0.0770087000
_diffrn_orient_matrix_UB_23      0.0471795000
_diffrn_orient_matrix_UB_31      -0.0779123000
_diffrn_orient_matrix_UB_32      0.0910846000
_diffrn_orient_matrix_UB_33      0.0250498000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 0.9992
_diffrn_reflns_Laue_measured_fraction_max 0.8749
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13896
_diffrn_reflns_point_group_measured_fraction_full 0.9850
_diffrn_reflns_point_group_measured_fraction_max 0.8186
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         31.36
_diffrn_reflns_theta_min         3.43
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59925
_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            'dull brownish brown'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_description       plate
_exptl_crystal_F_000             166.140
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.001
_refine_diff_density_max         0.1990
_refine_diff_density_min         -0.2040
_refine_diff_density_rms         0.0473
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.7(7)
_refine_ls_d_res_high            0.6829
_refine_ls_d_res_low             5.9401
_refine_ls_goodness_of_fit_ref   1.0394
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    23
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3692
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.0394
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0414
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0616P)^2^+0.0052P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1094
_reflns_Friedel_coverage         0.762
_reflns_limit_h_max              6
_reflns_limit_h_min              -7
_reflns_limit_k_max              9
_reflns_limit_k_min              -8
_reflns_limit_l_max              16
_reflns_limit_l_min              -16
_reflns_number_gt                2919
_reflns_number_total             3692
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d2ob01905a2.cif
_cod_data_source_block           NKS_MKG_TR-PEP
_cod_original_sg_symbol_Hall     ' P 1'
_cod_database_code               7158980
_chemical_oxdiff_formula         'C13 H15 N1 O8 '
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.82
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C7(H7), C4(H4), C5(H5), C6(H6), N1(H1)
2.d Idealised Me refined as rotating group:
 N2(H2a,H2b,H2c)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 1.737
_oxdiff_exptl_absorpt_empirical_full_min 0.581