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#$Date: 2025-08-22 01:24:23 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301857 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/30/7113086.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_7113086
loop_
_publ_author_name
'Shin, Dae-Seop'
'Masciocchi, Daniela'
'Gelain, Arianna'
'Villa, Stefania'
'Barlocco, Daniela'
'Meneghetti, Fiorella'
'Pedretti, Alessandro'
'Han, Young-Min'
'Han, Dong Cho'
'Kwon, Byoung-Mog'
'Legnani, Laura'
'Toma, Lucio'
_publ_section_title
;
 Synthesis, modeling, and crystallographic study of
 3,4-disubstituted-1,2,5-oxadiazoles and evaluation of their ability to
 decrease STAT3 activity
;
_journal_issue                   2
_journal_name_full               MedChemComm
_journal_page_first              156
_journal_paper_doi               10.1039/c0md00057d
_journal_volume                  1
_journal_year                    2010
_chemical_formula_sum            'C16 H10 Cl F3 N4 O2'
_chemical_formula_weight         382.73
_chemical_name_common            avs-0288
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.570(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.064(3)
_cell_length_b                   14.500(3)
_cell_length_c                   12.384(3)
_cell_measurement_temperature    293(2)
_cell_volume                     1605.0(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1344
_diffrn_reflns_av_sigmaI/netI    0.1212
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            3916
_diffrn_reflns_theta_full        25.96
_diffrn_reflns_theta_max         25.97
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    0.288
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.130
_refine_ls_extinction_coef       0.012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1771
_refine_ls_R_factor_gt           0.0493
_refine_ls_shift/su_max          0.156
_refine_ls_shift/su_mean         0.026
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0897P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1230
_reflns_number_gt                1376
_reflns_number_total             3166
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0md00057d.txt
_cod_data_source_block           avs2
_cod_original_cell_volume        1621.6(7)
_cod_database_code               7113086
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
Cl1 Cl -0.23391(14) 0.34215(11) 1.31017(11) 0.0895(6) Uani 1 1 d
O2 O 0.3604(3) 0.1928(2) 0.8089(2) 0.0576(8) Uani 1 1 d
N3 N 0.1611(4) 0.2609(3) 0.8683(3) 0.0473(10) Uani 1 1 d
H3 H 0.079(6) 0.260(3) 0.865(4) 0.066(15) Uiso 1 1 d
N4 N 0.1258(4) 0.1356(3) 0.7570(3) 0.0487(10) Uani 1 1 d
H4 H 0.061(6) 0.131(3) 0.779(4) 0.063(16) Uiso 1 1 d
C1 C 0.2053(4) 0.3886(3) 1.0052(3) 0.0468(10) Uani 1 1 d
N2 N 0.3520(4) 0.3722(3) 0.8785(3) 0.0638(11) Uani 1 1 d
O1 O 0.3919(4) 0.4463(3) 0.9440(3) 0.0856(12) Uani 1 1 d
C30 C 0.0915(4) 0.3755(3) 1.0763(3) 0.0452(10) Uani 1 1 d
C5 C 0.1598(4) 0.0656(3) 0.6874(3) 0.0398(9) Uani 1 1 d
C10 C 0.2673(5) 0.0784(3) 0.6211(3) 0.0502(11) Uani 1 1 d
H10 H 0.320(4) 0.134(3) 0.624(3) 0.047(11) Uiso 1 1 d
C8 C 0.2155(5) -0.0711(3) 0.5455(3) 0.0495(11) Uani 1 1 d
C33 C -0.1097(4) 0.3560(4) 1.2178(3) 0.0582(13) Uani 1 1 d
C31 C 0.0322(4) 0.2916(4) 1.0920(3) 0.0521(11) Uani 1 1 d
H31 H 0.063(5) 0.239(3) 1.063(3) 0.054(12) Uiso 1 1 d
N1 N 0.3001(4) 0.4559(3) 1.0219(3) 0.0767(13) Uani 1 1 d
C11 C 0.2249(4) 0.1959(3) 0.8097(3) 0.0409(10) Uani 1 1 d
C9 C 0.2941(5) 0.0093(3) 0.5508(3) 0.0524(11) Uani 1 1 d
H9 H 0.367(5) 0.022(3) 0.504(3) 0.070(13) Uiso 1 1 d
C32 C -0.0696(5) 0.2806(4) 1.1644(4) 0.0586(12) Uani 1 1 d
H32 H -0.096(4) 0.219(3) 1.175(3) 0.034(10) Uiso 1 1 d
C35 C 0.0486(5) 0.4507(4) 1.1322(4) 0.0567(12) Uani 1 1 d
H35 H 0.084(4) 0.507(3) 1.121(3) 0.042(12) Uiso 1 1 d
C34 C -0.0522(5) 0.4407(4) 1.2036(4) 0.0614(13) Uani 1 1 d
H34 H -0.081(6) 0.495(4) 1.241(4) 0.086(16) Uiso 1 1 d
C7 C 0.1086(5) -0.0822(4) 0.6111(4) 0.0612(13) Uani 1 1 d
H7 H 0.057(5) -0.133(3) 0.602(3) 0.046(12) Uiso 1 1 d
C6 C 0.0804(5) -0.0143(3) 0.6807(4) 0.0550(12) Uani 1 1 d
H6 H 0.028(6) -0.028(3) 0.730(4) 0.078(15) Uiso 1 1 d
C2 C 0.2377(4) 0.3361(3) 0.9140(3) 0.0456(10) Uani 1 1 d
F1 F 0.1379(4) -0.2021(3) 0.4433(3) 0.1185(13) Uani 1 1 d
F3 F 0.2802(7) -0.1137(3) 0.3784(3) 0.158(2) Uani 1 1 d
F2 F 0.3621(4) -0.1965(3) 0.5136(3) 0.1218(14) Uani 1 1 d
C12 C 0.2504(7) -0.1439(4) 0.4713(4) 0.0705(14) Uani 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
C11 N3 C2 122.9(3)
C11 N4 C5 125.3(3)
N1 C1 C2 108.4(3)
N1 C1 C30 120.7(3)
C2 C1 C30 130.9(4)
C2 N2 O1 105.5(3)
N2 O1 N1 111.4(3)
C31 C30 C35 119.5(4)
C31 C30 C1 122.0(4)
C35 C30 C1 118.4(4)
C6 C5 C10 119.6(4)
C6 C5 N4 119.6(3)
C10 C5 N4 120.8(4)
C9 C10 C5 119.2(4)
C7 C8 C9 119.0(4)
C7 C8 C12 121.8(5)
C9 C8 C12 119.1(4)
C32 C33 C34 122.2(4)
C32 C33 Cl1 118.4(4)
C34 C33 Cl1 119.4(3)
C30 C31 C32 120.8(5)
C1 N1 O1 105.6(3)
O2 C11 N4 123.9(3)
O2 C11 N3 122.4(4)
N4 C11 N3 113.7(3)
C8 C9 C10 121.0(4)
C33 C32 C31 118.2(5)
C34 C35 C30 120.4(5)
C33 C34 C35 119.0(5)
C6 C7 C8 120.7(5)
C7 C6 C5 120.5(4)
N2 C2 N3 124.2(4)
N2 C2 C1 109.0(4)
N3 C2 C1 126.8(3)
F3 C12 F2 107.0(5)
F3 C12 F1 104.5(5)
F2 C12 F1 103.6(4)
F3 C12 C8 113.7(4)
F2 C12 C8 114.1(5)
F1 C12 C8 113.0(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C33 1.745(4)
O2 C11 1.231(4)
N3 C11 1.381(5)
N3 C2 1.374(5)
N4 C11 1.349(5)
N4 C5 1.406(5)
C1 N1 1.301(5)
C1 C2 1.435(5)
C1 C30 1.477(5)
N2 C2 1.304(5)
N2 O1 1.368(5)
O1 N1 1.382(4)
C30 C31 1.368(6)
C30 C35 1.390(6)
C5 C6 1.370(6)
C5 C10 1.387(5)
C10 C9 1.383(6)
C8 C7 1.373(6)
C8 C9 1.373(6)
C8 C12 1.476(6)
C33 C32 1.368(7)
C33 C34 1.368(7)
C31 C32 1.398(6)
C35 C34 1.380(6)
C7 C6 1.369(6)
F1 C12 1.330(6)
F3 C12 1.302(6)
F2 C12 1.311(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 13454179
