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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/7/11/30/7113087.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_7113087
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            'C11 H11 N3 O2'
_chemical_formula_weight         217.23
_chemical_name_common            md30
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 103.72(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.619(2)
_cell_length_b                   20.540(3)
_cell_length_c                   8.364(5)
_cell_measurement_temperature    293(2)
_cell_volume                     1104.7(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0504
_diffrn_reflns_av_sigmaI/netI    0.0282
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2314
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.20
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2172
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0885
_refine_ls_R_factor_gt           0.0637
_refine_ls_shift/su_max          0.147
_refine_ls_shift/su_mean         0.008
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0818P)²+0.1219P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1816
_refine_ls_wR_factor_ref         0.1571
_reflns_number_gt                1395
_reflns_number_total             2172
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0md00057d.txt
_cod_data_source_block           fiomi-zan
_cod_database_code               7113087
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O -0.2400(3) 0.10115(11) 0.5186(3) 0.0909(7) Uani 1 1 d .
O2 O 0.3556(3) 0.22881(8) 0.63231(17) 0.0695(5) Uani 1 1 d .
N1 N -0.0617(4) 0.06930(11) 0.6000(3) 0.0766(7) Uani 1 1 d .
N2 N -0.1903(3) 0.15612(11) 0.4413(3) 0.0745(6) Uani 1 1 d .
N3 N 0.1097(3) 0.20512(9) 0.4055(2) 0.0511(5) Uani 1 1 d .
C11 C 0.2780(3) 0.23871(10) 0.4873(2) 0.0532(6) Uani 1 1 d .
C1 C 0.0920(3) 0.10268(11) 0.5742(3) 0.0543(6) Uani 1 1 d .
C2 C 0.0102(3) 0.15728(10) 0.4749(2) 0.0480(5) Uani 1 1 d .
C3 C 0.3085(5) 0.08117(17) 0.6380(5) 0.0815(9) Uani 1 1 d .
C4 C 0.3629(6) 0.28661(18) 0.3832(3) 0.0865(11) Uani 1 1 d .
H4A H 0.397(8) 0.272(2) 0.307(6) 0.16(2) Uiso 1 1 d .
H4B H 0.247(5) 0.3082(17) 0.309(4) 0.111(11) Uiso 1 1 d .
C6 C 0.7163(4) 0.32574(15) 0.5186(3) 0.0744(7) Uani 1 1 d .
H6 H 0.7703 0.2886 0.4803 0.089 Uiso 1 1 calc R
C5 C 0.5053(3) 0.33623(10) 0.4812(2) 0.0507(5) Uani 1 1 d .
C10 C 0.4339(5) 0.39179(13) 0.5398(3) 0.0768(8) Uani 1 1 d .
H10 H 0.2920 0.4004 0.5161 0.092 Uiso 1 1 calc R
C9 C 0.5715(11) 0.43470(15) 0.6332(5) 0.1260(18) Uani 1 1 d .
H9 H 0.5206 0.4723 0.6715 0.151 Uiso 1 1 calc R
C8 C 0.7711(12) 0.4244(3) 0.6697(5) 0.151(3) Uani 1 1 d .
H8 H 0.8608 0.4540 0.7346 0.181 Uiso 1 1 calc R
C7 C 0.8472(5) 0.3703(3) 0.6129(5) 0.1246(17) Uani 1 1 d .
H7 H 0.9900 0.3633 0.6379 0.150 Uiso 1 1 calc R
H3 H 0.047(4) 0.2194(12) 0.306(3) 0.066(7) Uiso 1 1 d .
H3A H 0.314(6) 0.040(2) 0.682(5) 0.157(16) Uiso 1 1 d .
H3B H 0.379(6) 0.111(2) 0.728(5) 0.144(15) Uiso 1 1 d .
H3C H 0.387(6) 0.079(2) 0.558(5) 0.145(16) 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
N2 O1 N1 110.41(17)
C1 N1 O1 106.4(2)
C2 N2 O1 105.1(2)
C11 N3 C2 124.55(18)
O2 C11 N3 121.5(2)
O2 C11 C4 123.9(2)
N3 C11 C4 114.62(18)
N1 C1 C2 108.1(2)
N1 C1 C3 121.3(2)
C2 C1 C3 130.5(2)
N2 C2 N3 119.2(2)
N2 C2 C1 110.0(2)
N3 C2 C1 130.62(19)
C5 C4 C11 113.7(2)
C5 C6 C7 119.6(3)
C10 C5 C6 117.9(2)
C10 C5 C4 122.6(3)
C6 C5 C4 119.5(3)
C5 C10 C9 120.0(3)
C8 C9 C10 122.0(4)
C9 C8 C7 119.6(4)
C8 C7 C6 120.8(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N2 1.379(3)
O1 N1 1.380(3)
O2 C11 1.217(2)
N1 C1 1.287(3)
N2 C2 1.290(3)
N3 C11 1.351(3)
N3 C2 1.385(3)
C11 C4 1.508(3)
C1 C2 1.424(3)
C1 C3 1.474(4)
C4 C5 1.494(3)
C6 C5 1.374(3)
C6 C7 1.374(5)
C5 C10 1.369(3)
C10 C9 1.371(6)
C9 C8 1.301(7)
C8 C7 1.351(7)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 3408634
