#------------------------------------------------------------------------------
#$Date: 2022-11-12 03:49:19 +0200 (Sat, 12 Nov 2022) $
#$Revision: 279240 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/89/7158980.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_7158980
loop_
_publ_author_name
'Sharma, Nagendra K.'
'Gupta, Manish Kumar'
_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 & 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  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -29.00  38.00   0.50   24.00    --    6.83 -91.00-112.00  134
  2  ω    -29.00  24.00   0.50   24.00    --   -7.14 -91.00-112.00  106
  3  ω    -38.00   8.00   0.50   24.00    --   -7.14  91.00   1.00   92
  4  ω      1.00  76.00   0.50   24.00    --    6.83  19.00  60.00  150
  5  ω    -61.00  13.00   0.50   24.00    --    6.83 -19.00  90.00  148
  6  ω      4.00  73.00   0.50   24.00    --    6.83  38.00 120.00  138
  7  ω     -9.00  50.00   0.50   24.00    --    6.83-111.00 176.63  118
  8  ω      1.00  76.00   0.50   24.00    --    6.83  19.00 -60.00  150
  9  ω      4.00  73.00   0.50   24.00    --    6.83  38.00-180.00  138
 10  ω    -59.00  10.00   0.50   24.00    --    6.83 -38.00 -30.00  138
 11  ω     -5.00  70.00   0.50   24.00    --    6.83  57.00  60.00  150
 12  ω    -70.00   4.00   0.50   24.00    --   -7.14 -57.00-180.00  148
 13  ω    -68.00 -33.00   0.50   24.00    --   -7.14 141.00  97.62   70
 14  ω    -59.00 -24.00   0.50   24.00    --   -7.14 126.00-135.18   70
 15  ω    -75.00 -36.00   0.50   24.00    --   -7.14 150.00-129.34   78
 16  ω    -20.00  29.00   0.50   24.00    --   -7.14 -99.00-120.00   98
 17  ω    -61.00 -27.00   0.50   24.00    --   -7.14 129.00  -8.08   68
 18  ω    -60.00 -26.00   0.50   24.00    --   -7.14 128.00 -45.63   68
 19  ω    -71.00  16.00   0.50   24.00    --   -7.14 -77.00  60.00  174
 20  ω    -63.00 -29.00   0.50   24.00    --   -7.14 133.00 175.22   68
 21  ω    -62.00 -27.00   0.50   24.00    --   -7.14 131.00  33.77   70
 22  ω      4.00  73.00   0.50   24.00    --    6.83  38.00-150.00  138
 23  ω    -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       'ω 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/[σ²(Fo²)+(0.0616P)²+0.0052P] where P=(Fo²+2Fc²)/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
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
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_refinement_flags_posn
O2 O -1.0935(3) -0.6033(2) -0.39951(12) 0.0470(3) Uani 1.000000 .
O3 O -1.0890(3) -0.6103(2) -0.58910(12) 0.0469(3) Uani 1.000000 .
O1 O -0.4272(3) 0.1345(2) -0.38094(12) 0.0430(3) Uani 1.000000 .
O4 O -0.5042(3) -0.8324(2) -0.68238(12) 0.0481(3) Uani 1.000000 .
F1 F -0.2421(4) -0.5670(2) -0.85043(15) 0.0876(6) Uani 1.000000 .
O5 O -0.2344(3) -1.1364(2) -0.73509(16) 0.0575(4) Uani 1.000000 .
N1 N -0.7018(3) -0.1042(2) -0.44520(13) 0.0358(3) Uani 1.000000 .
F3 F -0.2423(4) -0.8080(3) -0.95249(12) 0.0836(5) Uani 1.000000 .
C10 C -1.0068(4) -0.5530(3) -0.51201(16) 0.0343(4) Uani 1.000000 .
N2 N -0.6765(3) -0.3852(2) -0.66160(14) 0.0387(3) Uani 1.000000 .
F2 F 0.0943(3) -0.8408(4) -0.85567(17) 0.0939(6) Uani 1.000000 .
C11 C -0.3197(4) -0.9313(3) -0.74492(16) 0.0373(4) Uani 1.000000 .
C2 C -0.6877(4) -0.1447(3) -0.32898(15) 0.0353(4) Uani 1.000000 .
C1 C -0.5315(3) 0.0016(3) -0.29519(16) 0.0351(3) Uani 1.000000 .
C9 C -0.7836(3) -0.4105(3) -0.53510(15) 0.0325(3) Uani 1.000000 .
C8 C -0.8929(4) -0.1805(3) -0.50085(16) 0.0360(4) Uani 1.000000 .
C3 C -0.8124(4) -0.3115(3) -0.25178(18) 0.0477(5) Uani 1.000000 .
C12 C -0.1774(5) -0.7845(3) -0.85118(18) 0.0477(5) Uani 1.000000 .
C7 C -0.4937(5) 0.0000(4) -0.1779(2) 0.0516(5) Uani 1.000000 .
C4 C -0.8324(6) -0.3766(4) -0.1304(2) 0.0623(6) Uani 1.000000 .
C5 C -0.7347(7) -0.2968(5) -0.0486(2) 0.0709(7) Uani 1.000000 .
C6 C -0.5832(6) -0.1272(5) -0.0716(2) 0.0675(7) Uani 1.000000 .
H9 H -0.6321(3) -0.4917(3) -0.48822(15) 0.0390(4) Uiso 1.000000 R
H8a H -1.0619(4) -0.1887(3) -0.44758(16) 0.0432(4) Uiso 1.000000 R
H8b H -0.9399(4) -0.0693(3) -0.57134(16) 0.0432(4) Uiso 1.000000 R
H3 H -0.8964(4) -0.3926(3) -0.28849(18) 0.0572(5) Uiso 1.000000 R
H7 H -0.3899(5) 0.1031(4) -0.1713(2) 0.0619(6) Uiso 1.000000 R
H4 H -0.9278(6) -0.4937(4) -0.0990(2) 0.0748(7) Uiso 1.000000 R
H5 H -0.7742(7) -0.3633(5) 0.0302(2) 0.0851(9) Uiso 1.000000 R
H6 H -0.5342(6) -0.0936(5) -0.0053(2) 0.0810(8) Uiso 1.000000 R
H1 H -0.5884(3) -0.0266(2) -0.49040(13) 0.0429(4) Uiso 1.000000 R
H2a H -0.8118(8) -0.310(2) -0.70523(14) 0.0464(4) Uiso 1.000000 GR
H2b H -0.5385(19) -0.309(2) -0.6767(3) 0.0464(4) Uiso 1.000000 GR
H2c H -0.615(3) -0.5206(2) -0.6789(3) 0.0464(4) Uiso 1.000000 GR
H2 H -1.189(5) -0.700(4) -0.3882(4) 0.0705(5) Uiso 1.000000 GR
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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 N1 C2 125.15(14) . . ?
O3 C10 O2 125.38(15) . . ?
C9 C10 O2 111.64(14) . . ?
C9 C10 O3 122.98(16) . . ?
O5 C11 O4 128.39(18) . . ?
C12 C11 O4 116.84(16) . . ?
C12 C11 O5 114.76(17) . . ?
C1 C2 N1 113.09(14) . . ?
C3 C2 N1 121.13(16) . . ?
C3 C2 C1 125.78(17) . . ?
C2 C1 O1 114.60(16) . . ?
C7 C1 O1 120.63(16) . . ?
C7 C1 C2 124.77(17) . . ?
N2 C9 C10 107.57(14) . . ?
C8 C9 C10 112.16(13) . . ?
C8 C9 N2 111.40(13) . . ?
C9 C8 N1 114.77(14) . . ?
C4 C3 C2 131.10(19) . . ?
F3 C12 F1 106.7(2) . . ?
F2 C12 F1 106.62(19) . . ?
F2 C12 F3 106.4(2) . . ?
C11 C12 F1 113.64(17) . . ?
C11 C12 F3 111.62(17) . . ?
C11 C12 F2 111.46(18) . . ?
C6 C7 C1 131.5(2) . . ?
C5 C4 C3 130.5(2) . . ?
C6 C5 C4 126.4(2) . . ?
C5 C6 C7 129.8(2) . . ?
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
O2 C10 1.309(2) . ?
O3 C10 1.200(2) . ?
O1 C1 1.266(2) . ?
O4 C11 1.229(2) . ?
F1 C12 1.322(3) . ?
O5 C11 1.238(2) . ?
N1 C2 1.338(2) . ?
N1 C8 1.447(2) . ?
F3 C12 1.326(3) . ?
C10 C9 1.524(2) . ?
N2 C9 1.480(2) . ?
F2 C12 1.317(3) . ?
C11 C12 1.539(3) . ?
C2 C1 1.471(2) . ?
C2 C3 1.397(2) . ?
C1 C7 1.415(3) . ?
C9 C8 1.537(2) . ?
C3 C4 1.381(3) . ?
C7 C6 1.379(4) . ?
C4 C5 1.370(4) . ?
C5 C6 1.381(4) . ?
