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#$Date: 2025-04-05 07:03:05 +0300 (Sat, 05 Apr 2025) $
#$Revision: 299092 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/02/7160238.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_7160238
loop_
_publ_author_name
'Saravanakumar, Srinivasan Pon'
'Nagasundaram, Nagarajan'
'DhineshKumar, Jayaraman'
'Rajalakshmi, Periyaswamy'
'Lalitha, Appaswami'
_publ_section_title
;
 TFAA mediated one-pot synthesis of chiral N-protected amino
 acid-derived 1,2,4-oxadiazoles and their antibacterial studies.
;
_journal_issue                   2
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              360
_journal_page_last               368
_journal_paper_doi               10.1039/d4ob01509f
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C12 H8 F5 N3 O2'
_chemical_formula_sum            'C12 H8 F5 N3 O2'
_chemical_formula_weight         321.21
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_block_doi                 10.5517/ccdc.csd.cc2l0vxd
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-09-14 deposited with the CCDC.	2024-11-04 downloaded from the CCDC.
;
_cell_angle_alpha                97.903(2)
_cell_angle_beta                 98.647(2)
_cell_angle_gamma                97.738(2)
_cell_formula_units_Z            2
_cell_length_a                   5.2116(2)
_cell_length_b                   7.7885(3)
_cell_length_c                   16.4336(7)
_cell_measurement_reflns_used    9901
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      69.88
_cell_measurement_theta_min      2.76
_cell_volume                     644.93(5)
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997) '
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type
'Bruker D8 VENTURE diffractometer with PHOTON II detector'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_radiation_source         'micro-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            20587
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.211
_diffrn_reflns_theta_min         2.756
_exptl_absorpt_coefficient_mu    1.458
_exptl_absorpt_correction_T_max  0.8404
_exptl_absorpt_correction_T_min  0.7143
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.654
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.103
_refine_diff_density_max         0.895
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         2434
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0731
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1292P)²+0.4810P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2152
_refine_ls_wR_factor_ref         0.2304
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2022
_reflns_number_total             2434
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob01509f2.cif
_cod_data_source_block           SP302F
_cod_depositor_comments          'Adding full bibliography for 7160238.cif.'
_cod_original_cell_volume        644.93(4)
_cod_database_code               7160238
_shelx_shelxl_version_number     2018/3
_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.
;
_shelx_estimated_absorpt_t_min   0.677
_shelx_estimated_absorpt_t_max   0.864
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-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_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
C1 C 0.3804(6) 0.6886(4) 0.5720(2) 0.0573(8) Uani 1 1 d . . . . .
H1 H 0.217361 0.616857 0.559773 0.069 Uiso 1 1 calc R U . . .
C2 C 0.5076(8) 0.7418(5) 0.6538(2) 0.0640(9) Uani 1 1 d . . . . .
C3 C 0.7462(7) 0.8457(5) 0.6724(2) 0.0626(8) Uani 1 1 d . . . . .
C4 C 0.8703(7) 0.9002(5) 0.6110(2) 0.0694(9) Uani 1 1 d . . . . .
H4 H 1.034481 0.970604 0.624082 0.083 Uiso 1 1 calc R U . . .
C5 C 0.7485(7) 0.8494(5) 0.5295(2) 0.0618(8) Uani 1 1 d . . . . .
H5 H 0.832295 0.885330 0.487152 0.074 Uiso 1 1 calc R U . . .
C6 C 0.5027(6) 0.7454(4) 0.50897(18) 0.0492(7) Uani 1 1 d . . . . .
C7 C 0.3751(5) 0.6975(4) 0.42135(18) 0.0485(7) Uani 1 1 d . . . . .
C8 C 0.3108(5) 0.6795(4) 0.29188(17) 0.0476(7) Uani 1 1 d . . . . .
C9 C 0.3115(5) 0.6907(4) 0.20107(17) 0.0471(7) Uani 1 1 d . . . . .
H10 H 0.157883 0.742495 0.180500 0.057 Uiso 1 1 calc R U . . .
C10 C 0.5541(6) 0.8072(5) 0.1886(2) 0.0600(8) Uani 1 1 d . . . . .
H10A H 0.708081 0.764373 0.212363 0.090 Uiso 1 1 calc R U . . .
H10B H 0.555937 0.924973 0.215511 0.090 Uiso 1 1 calc R U . . .
H10C H 0.552302 0.806264 0.130056 0.090 Uiso 1 1 calc R U . . .
C11 C 0.0498(6) 0.4218(4) 0.11996(18) 0.0521(7) Uani 1 1 d . . . . .
C12 C 0.0553(7) 0.2486(5) 0.0639(2) 0.0646(9) Uani 1 1 d . . . . .
N1 N 0.4877(5) 0.7496(3) 0.35608(14) 0.0492(6) Uani 1 1 d . . . . .
N2 N 0.1447(6) 0.6037(4) 0.39894(17) 0.0662(8) Uani 1 1 d . . . . .
N3 N 0.2855(5) 0.5150(3) 0.15323(15) 0.0496(6) Uani 1 1 d . . . . .
O1 O 0.0983(4) 0.5895(3) 0.31138(13) 0.0663(7) Uani 1 1 d . . . . .
O2 O -0.1597(4) 0.4646(3) 0.12877(16) 0.0694(7) Uani 1 1 d . . . . .
F1 F 0.8614(5) 0.8942(4) 0.75312(12) 0.0893(8) Uani 1 1 d . . . . .
F2 F 0.3964(6) 0.6940(4) 0.71635(15) 0.1006(9) Uani 1 1 d . . . . .
F3 F -0.0175(9) 0.2606(4) -0.01343(15) 0.1349(14) Uani 1 1 d . . . . .
F4 F -0.1121(6) 0.1200(3) 0.08058(19) 0.1066(9) Uani 1 1 d . . . . .
F5 F 0.2815(6) 0.1930(4) 0.0742(2) 0.1202(12) Uani 1 1 d . . . . .
H3A H 0.415(8) 0.475(5) 0.143(2) 0.066(11) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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
C2 C1 C6 118.3(3) . . ?
C2 C1 H1 120.9 . . ?
C6 C1 H1 120.9 . . ?
F2 C2 C3 118.1(3) . . ?
F2 C2 C1 120.6(4) . . ?
C3 C2 C1 121.3(3) . . ?
F1 C3 C2 119.0(3) . . ?
F1 C3 C4 120.0(3) . . ?
C2 C3 C4 121.0(3) . . ?
C3 C4 C5 118.8(4) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C4 C5 C6 121.3(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 119.3(3) . . ?
C1 C6 C7 120.9(3) . . ?
C5 C6 C7 119.8(3) . . ?
N2 C7 N1 114.2(3) . . ?
N2 C7 C6 122.4(3) . . ?
N1 C7 C6 123.4(3) . . ?
N1 C8 O1 113.5(3) . . ?
N1 C8 C9 129.1(3) . . ?
O1 C8 C9 117.4(2) . . ?
N3 C9 C8 110.0(2) . . ?
N3 C9 C10 111.2(2) . . ?
C8 C9 C10 111.8(2) . . ?
N3 C9 H10 107.9 . . ?
C8 C9 H10 107.9 . . ?
C10 C9 H10 107.9 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 N3 125.9(3) . . ?
O2 C11 C12 119.1(3) . . ?
N3 C11 C12 115.1(3) . . ?
F3 C12 F5 110.3(4) . . ?
F3 C12 F4 106.4(3) . . ?
F5 C12 F4 104.3(3) . . ?
F3 C12 C11 110.6(3) . . ?
F5 C12 C11 114.1(3) . . ?
F4 C12 C11 110.8(3) . . ?
C8 N1 C7 102.4(2) . . ?
C7 N2 O1 103.9(2) . . ?
C11 N3 C9 121.3(2) . . ?
C11 N3 H3A 118(3) . . ?
C9 N3 H3A 120(3) . . ?
C8 O1 N2 105.9(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
C1 C2 1.387(5) . ?
C1 C6 1.387(4) . ?
C1 H1 0.9300 . ?
C2 F2 1.325(4) . ?
C2 C3 1.357(5) . ?
C3 F1 1.351(4) . ?
C3 C4 1.362(5) . ?
C4 C5 1.373(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.467(4) . ?
C7 N2 1.292(4) . ?
C7 N1 1.380(4) . ?
C8 N1 1.294(4) . ?
C8 O1 1.334(3) . ?
C8 C9 1.507(4) . ?
C9 N3 1.460(4) . ?
C9 C10 1.511(4) . ?
C9 H10 0.9800 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 O2 1.207(4) . ?
C11 N3 1.335(4) . ?
C11 C12 1.532(5) . ?
C12 F3 1.290(4) . ?
C12 F5 1.305(4) . ?
C12 F4 1.324(4) . ?
N2 O1 1.409(3) . ?
N3 H3A 0.81(4) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1 N2 0.93 2.61 3.452(4) 151.0 2_566 yes
N3 H3A O2 0.81(4) 2.28(4) 3.048(3) 160(4) 1_655 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 F2 178.6(3) . . . . ?
C6 C1 C2 C3 -0.4(5) . . . . ?
F2 C2 C3 F1 0.8(5) . . . . ?
C1 C2 C3 F1 179.8(3) . . . . ?
F2 C2 C3 C4 -179.6(3) . . . . ?
C1 C2 C3 C4 -0.6(5) . . . . ?
F1 C3 C4 C5 -179.8(3) . . . . ?
C2 C3 C4 C5 0.6(6) . . . . ?
C3 C4 C5 C6 0.4(6) . . . . ?
C2 C1 C6 C5 1.3(5) . . . . ?
C2 C1 C6 C7 -178.4(3) . . . . ?
C4 C5 C6 C1 -1.4(5) . . . . ?
C4 C5 C6 C7 178.3(3) . . . . ?
C1 C6 C7 N2 0.9(5) . . . . ?
C5 C6 C7 N2 -178.8(3) . . . . ?
C1 C6 C7 N1 -179.8(3) . . . . ?
C5 C6 C7 N1 0.5(4) . . . . ?
N1 C8 C9 N3 121.8(3) . . . . ?
O1 C8 C9 N3 -60.2(3) . . . . ?
N1 C8 C9 C10 -2.3(4) . . . . ?
O1 C8 C9 C10 175.8(3) . . . . ?
O2 C11 C12 F3 71.0(4) . . . . ?
N3 C11 C12 F3 -107.1(4) . . . . ?
O2 C11 C12 F5 -163.9(3) . . . . ?
N3 C11 C12 F5 17.9(4) . . . . ?
O2 C11 C12 F4 -46.6(4) . . . . ?
N3 C11 C12 F4 135.2(3) . . . . ?
O1 C8 N1 C7 0.3(3) . . . . ?
C9 C8 N1 C7 178.5(3) . . . . ?
N2 C7 N1 C8 -0.6(3) . . . . ?
C6 C7 N1 C8 -179.9(3) . . . . ?
N1 C7 N2 O1 0.6(4) . . . . ?
C6 C7 N2 O1 180.0(3) . . . . ?
O2 C11 N3 C9 -4.3(5) . . . . ?
C12 C11 N3 C9 173.7(3) . . . . ?
C8 C9 N3 C11 89.6(3) . . . . ?
C10 C9 N3 C11 -146.0(3) . . . . ?
N1 C8 O1 N2 0.0(4) . . . . ?
C9 C8 O1 N2 -178.3(3) . . . . ?
C7 N2 O1 C8 -0.4(3) . . . . ?
