#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/60/2226055.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2226055
loop_
_publ_author_name
'Ünver, Yasemin'
'Köysal, Yavuz'
'Tanak, Hasan'
'Ünlüer, Dilek'
'Işık, Şamil'
_publ_section_title
;
 Ethyl
 4-(3-ethyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-4-yl)benzoate
;
_journal_coeditor_code           BT5258
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1294
_journal_paper_doi               10.1107/S160053681001603X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C13 H15 N3 O3'
_chemical_formula_moiety         'C13 H15 N3 O3'
_chemical_formula_sum            'C13 H15 N3 O3'
_chemical_formula_weight         261.28
_chemical_name_systematic
;
Ethyl 4-(3-ethyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-4-yl)benzoate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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                 100.063(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.6111(11)
_cell_length_b                   4.0970(2)
_cell_length_c                   24.172(2)
_cell_measurement_reflns_used    10833
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.17
_cell_measurement_theta_min      1.52
_cell_volume                     1327.21(17)
_computing_cell_refinement       'X-AREA (Stoe & Cie, 2002)'
_computing_data_collection       'X-AREA (Stoe & Cie, 2002)'
_computing_data_reduction        'X-RED32 (Stoe & Cie, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Stoe IPDS 2'
_diffrn_measurement_method       'rotation method'
_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  0.0417
_diffrn_reflns_av_sigmaI/netI    0.0432
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            8189
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.61
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.800
_exptl_crystal_size_mid          0.410
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.135
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.928
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         2581
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.928
_refine_ls_R_factor_all          0.0776
_refine_ls_R_factor_gt           0.0380
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0488P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0948
_reflns_number_gt                1606
_reflns_number_total             2581
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt5258.cif
_cod_data_source_block           I
_cod_original_cell_volume        1327.20(17)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2226055
_cod_database_fobs_code          2226055
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.44143(13) 0.7739(5) 0.05726(6) 0.0485(5) Uani d . 1 . .
C C2 0.51671(12) 0.5332(4) 0.13682(6) 0.0440(4) Uani d . 1 . .
C C3 0.53173(14) 0.3581(6) 0.19150(8) 0.0525(5) Uani d . 1 . .
C C4 0.63819(16) 0.2621(7) 0.21203(9) 0.0631(6) Uani d . 1 . .
C C5 0.32736(11) 0.5585(5) 0.11912(6) 0.0432(4) Uani d . 1 . .
C C6 0.30553(12) 0.6504(5) 0.17095(6) 0.0466(5) Uani d . 1 . .
H H6 0.3534 0.7542 0.1973 0.056 Uiso calc R 1 . .
C C7 0.21229(12) 0.5858(5) 0.18282(6) 0.0473(4) Uani d . 1 . .
H H7 0.1975 0.6437 0.2177 0.057 Uiso calc R 1 . .
C C8 0.14040(12) 0.4365(5) 0.14379(6) 0.0450(4) Uani d . 1 . .
C C9 0.16301(13) 0.3535(5) 0.09164(7) 0.0533(5) Uani d . 1 . .
H H9 0.1146 0.2559 0.0648 0.064 Uiso calc R 1 . .
C C10 0.25609(12) 0.4141(5) 0.07938(6) 0.0515(5) Uani d . 1 . .
H H10 0.2708 0.3579 0.0445 0.062 Uiso calc R 1 . .
C C11 0.04218(13) 0.3608(5) 0.15961(7) 0.0512(5) Uani d . 1 . .
C C12 -0.11800(16) 0.1271(8) 0.13044(10) 0.0724(7) Uani d . 1 . .
C C13 -0.1753(2) -0.0096(12) 0.07756(15) 0.1015(11) Uani d . 1 . .
N N1 0.54074(11) 0.7686(5) 0.06243(6) 0.0562(5) Uani d . 1 . .
N N2 0.58809(10) 0.6223(4) 0.11107(5) 0.0519(4) Uani d . 1 . .
N N3 0.42458(9) 0.6181(4) 0.10615(5) 0.0447(4) Uani d . 1 . .
O O1 0.37870(9) 0.8859(4) 0.01948(5) 0.0624(4) Uani d . 1 . .
O O2 0.02253(9) 0.4134(4) 0.20563(5) 0.0726(5) Uani d . 1 . .
O O3 -0.02131(9) 0.2283(4) 0.11801(5) 0.0660(4) Uani d . 1 . .
H H1 0.5731(14) 0.864(5) 0.0382(8) 0.062(6) Uiso d . 1 . .
H H3A 0.4910(15) 0.170(5) 0.1871(8) 0.069(6) Uiso d . 1 . .
H H3B 0.5059(14) 0.489(5) 0.2178(8) 0.065(6) Uiso d . 1 . .
H H4A 0.6436(14) 0.140(5) 0.2481(9) 0.074(6) Uiso d . 1 . .
H H4B 0.6795(18) 0.443(6) 0.2188(9) 0.090(8) Uiso d . 1 . .
H H4C 0.6648(16) 0.115(6) 0.1853(10) 0.086(7) Uiso d . 1 . .
H H12A -0.1044(16) -0.029(6) 0.1621(9) 0.085(7) Uiso d . 1 . .
H H12B -0.1459(17) 0.324(6) 0.1422(9) 0.083(8) Uiso d . 1 . .
H H13A -0.234(2) -0.096(8) 0.0840(12) 0.126(10) Uiso d . 1 . .
H H13B -0.138(3) -0.175(9) 0.0604(14) 0.153(16) Uiso d . 1 . .
H H13C -0.189(2) 0.174(8) 0.0528(12) 0.120(12) Uiso d . 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 N1 . . 129.64(15) ?
O1 C1 N3 . . 127.27(15) ?
N1 C1 N3 . . 103.09(14) ?
N2 C2 N3 . . 110.93(14) ?
N2 C2 C3 . . 124.44(15) ?
N3 C2 C3 . . 124.63(14) ?
C2 C3 C4 . . 113.30(17) ?
C2 C3 H3A . . 107.9(12) ?
C4 C3 H3A . . 109.7(12) ?
C2 C3 H3B . . 108.3(12) ?
C4 C3 H3B . . 112.2(11) ?
H3A C3 H3B . . 105.0(17) ?
C3 C4 H4A . . 109.9(12) ?
C3 C4 H4B . . 111.7(15) ?
H4A C4 H4B . . 107.3(17) ?
C3 C4 H4C . . 112.6(13) ?
H4A C4 H4C . . 106.5(18) ?
H4B C4 H4C . . 109(2) ?
C10 C5 C6 . . 120.72(15) ?
C10 C5 N3 . . 119.11(14) ?
C6 C5 N3 . . 120.16(14) ?
C7 C6 C5 . . 119.14(15) ?
C7 C6 H6 . . 120.4 ?
C5 C6 H6 . . 120.4 ?
C6 C7 C8 . . 120.88(15) ?
C6 C7 H7 . . 119.6 ?
C8 C7 H7 . . 119.6 ?
C7 C8 C9 . . 119.07(15) ?
C7 C8 C11 . . 118.65(14) ?
C9 C8 C11 . . 122.26(15) ?
C10 C9 C8 . . 120.66(16) ?
C10 C9 H9 . . 119.7 ?
C8 C9 H9 . . 119.7 ?
C9 C10 C5 . . 119.49(15) ?
C9 C10 H10 . . 120.3 ?
C5 C10 H10 . . 120.3 ?
O2 C11 O3 . . 123.57(16) ?
O2 C11 C8 . . 123.62(16) ?
O3 C11 C8 . . 112.81(14) ?
O3 C12 C13 . . 106.6(2) ?
O3 C12 H12A . . 106.8(13) ?
C13 C12 H12A . . 114.8(13) ?
O3 C12 H12B . . 103.8(14) ?
C13 C12 H12B . . 113.4(14) ?
H12A C12 H12B . . 110(2) ?
C12 C13 H13A . . 110.1(18) ?
C12 C13 H13B . . 113(2) ?
H13A C13 H13B . . 110(3) ?
C12 C13 H13C . . 104.8(18) ?
H13A C13 H13C . . 109(2) ?
H13B C13 H13C . . 110(3) ?
C1 N1 N2 . . 113.73(14) ?
C1 N1 H1 . . 123.0(12) ?
N2 N1 H1 . . 123.1(12) ?
C2 N2 N1 . . 104.77(13) ?
C2 N3 C1 . . 107.48(13) ?
C2 N3 C5 . . 128.63(13) ?
C1 N3 C5 . . 123.87(13) ?
C11 O3 C12 . . 116.92(15) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 . 1.2251(19) ?
C1 N1 . 1.336(2) ?
C1 N3 . 1.397(2) ?
C2 N2 . 1.295(2) ?
C2 N3 . 1.385(2) ?
C2 C3 . 1.486(2) ?
C3 C4 . 1.500(3) ?
C3 H3A . 0.94(2) ?
C3 H3B . 0.95(2) ?
C4 H4A . 1.00(2) ?
C4 H4B . 0.93(3) ?
C4 H4C . 1.00(2) ?
C5 C10 . 1.374(2) ?
C5 C6 . 1.389(2) ?
C5 N3 . 1.433(2) ?
C6 C7 . 1.375(2) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.378(2) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.391(2) ?
C8 C11 . 1.486(2) ?
C9 C10 . 1.373(2) ?
C9 H9 . 0.9300 ?
C10 H10 . 0.9300 ?
C11 O2 . 1.2080(19) ?
C11 O3 . 1.322(2) ?
C12 O3 . 1.460(2) ?
C12 C13 . 1.486(4) ?
C12 H12A . 0.99(2) ?
C12 H12B . 0.96(2) ?
C13 H13A . 0.92(3) ?
C13 H13B . 0.98(4) ?
C13 H13C . 0.96(3) ?
N1 N2 . 1.376(2) ?
N1 H1 . 0.883(19) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1 O1 3_675 0.883(19) 1.94(2) 2.808(2) 169.5(18)
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N2 C2 C3 C4 . . . . -5.8(3) ?
N3 C2 C3 C4 . . . . 173.1(2) ?
C10 C5 C6 C7 . . . . 2.0(3) ?
N3 C5 C6 C7 . . . . -178.93(17) ?
C5 C6 C7 C8 . . . . -1.0(3) ?
C6 C7 C8 C9 . . . . -0.6(3) ?
C6 C7 C8 C11 . . . . 177.66(18) ?
C7 C8 C9 C10 . . . . 1.1(3) ?
C11 C8 C9 C10 . . . . -177.07(19) ?
C8 C9 C10 C5 . . . . -0.1(3) ?
C6 C5 C10 C9 . . . . -1.5(3) ?
N3 C5 C10 C9 . . . . 179.42(17) ?
C7 C8 C11 O2 . . . . -2.5(3) ?
C9 C8 C11 O2 . . . . 175.7(2) ?
C7 C8 C11 O3 . . . . 177.81(17) ?
C9 C8 C11 O3 . . . . -4.0(3) ?
O1 C1 N1 N2 . . . . 179.7(2) ?
N3 C1 N1 N2 . . . . -0.3(2) ?
N3 C2 N2 N1 . . . . 0.0(2) ?
C3 C2 N2 N1 . . . . 178.99(19) ?
C1 N1 N2 C2 . . . . 0.2(2) ?
N2 C2 N3 C1 . . . . -0.1(2) ?
C3 C2 N3 C1 . . . . -179.15(19) ?
N2 C2 N3 C5 . . . . 178.63(17) ?
C3 C2 N3 C5 . . . . -0.4(3) ?
O1 C1 N3 C2 . . . . -179.77(19) ?
N1 C1 N3 C2 . . . . 0.23(19) ?
O1 C1 N3 C5 . . . . 1.4(3) ?
N1 C1 N3 C5 . . . . -178.60(16) ?
C10 C5 N3 C2 . . . . -128.50(19) ?
C6 C5 N3 C2 . . . . 52.4(3) ?
C10 C5 N3 C1 . . . . 50.1(3) ?
C6 C5 N3 C1 . . . . -129.01(19) ?
O2 C11 O3 C12 . . . . -3.3(3) ?
C8 C11 O3 C12 . . . . 176.4(2) ?
C13 C12 O3 C11 . . . . 179.5(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745013
