#------------------------------------------------------------------------------
#$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2224129.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_2224129
loop_
_publ_author_name
'Tanak, Hasan'
'K\"oysal, Yavuz'
'Yavuz, Metin'
'I\,s\?ik, \,Samil'
'G\"ul, G\"ul\,sah'
_publ_section_title
;
4-(2,3-Dihydroxybenzylideneamino)-3-methyl-1H-1,2,4-triazol-5(4H)-one
;
_journal_coeditor_code BT5118
_journal_issue 12
_journal_name_full 'Acta Crystallographica Section E'
_journal_page_first o3039
_journal_volume 65
_journal_year 2009
_chemical_formula_iupac 'C10 H10 N4 O3'
_chemical_formula_moiety 'C10 H10 N4 O3'
_chemical_formula_sum 'C10 H10 N4 O3'
_chemical_formula_weight 234.22
_chemical_name_systematic
;
4-(2,3-Dihydroxybenzylideneamino)-3-methyl-1H-1,2,4-triazol-
5(4H)-one
;
_space_group_IT_number 5
_symmetry_cell_setting monoclinic
_symmetry_space_group_name_Hall 'C 2y'
_symmetry_space_group_name_H-M 'C 1 2 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 93.857(17)
_cell_angle_gamma 90.00
_cell_formula_units_Z 4
_cell_length_a 13.944(3)
_cell_length_b 6.2551(7)
_cell_length_c 11.882(2)
_cell_measurement_reflns_used 4561
_cell_measurement_temperature 296(2)
_cell_measurement_theta_max 27.95
_cell_measurement_theta_min 1.72
_cell_volume 1034.0(3)
_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 296(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type 'Stoe IPDS II'
_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 0.0355
_diffrn_reflns_av_sigmaI/netI 0.0256
_diffrn_reflns_limit_h_max 17
_diffrn_reflns_limit_h_min -17
_diffrn_reflns_limit_k_max 7
_diffrn_reflns_limit_k_min -7
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_number 3000
_diffrn_reflns_theta_full 25.99
_diffrn_reflns_theta_max 25.99
_diffrn_reflns_theta_min 1.72
_exptl_absorpt_coefficient_mu 0.115
_exptl_absorpt_correction_T_max 0.9737
_exptl_absorpt_correction_T_min 0.9436
_exptl_absorpt_correction_type integration
_exptl_absorpt_process_details '(X-RED32; Stoe & Cie, 2002)'
_exptl_crystal_colour yellow
_exptl_crystal_density_diffrn 1.505
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description prism.
_exptl_crystal_F_000 488
_exptl_crystal_size_max 0.600
_exptl_crystal_size_mid 0.420
_exptl_crystal_size_min 0.200
_refine_diff_density_max 0.305
_refine_diff_density_min -0.272
_refine_ls_extinction_coef 0.014(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method 'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref 1.089
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 159
_refine_ls_number_reflns 1118
_refine_ls_number_restraints 1
_refine_ls_restrained_S_all 1.088
_refine_ls_R_factor_all 0.0402
_refine_ls_R_factor_gt 0.0383
_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/[\s^2^(Fo^2^)+(0.0817P)^2^+0.2531P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1148
_refine_ls_wR_factor_ref 0.1163
_reflns_number_gt 1058
_reflns_number_total 1118
_reflns_threshold_expression I>2\s(I)
_[local]_cod_data_source_file bt5118.cif
_[local]_cod_data_source_block I
_[local]_cod_cif_authors_sg_H-M 'C 2'
_cod_database_code 2224129
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
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
C C1 0.42468(17) 0.3934(5) 0.2738(2) 0.0359(6) Uani d . 1
C C2 0.4051(2) 0.2125(6) 0.3388(2) 0.0437(7) Uani d . 1
H H8 0.4384 0.1927 0.4084 0.052 Uiso calc R 1
C C3 0.3379(2) 0.0655(5) 0.3012(3) 0.0468(7) Uani d . 1
H H9 0.3259 -0.0535 0.3451 0.056 Uiso calc R 1
C C4 0.28754(19) 0.0937(5) 0.1977(3) 0.0423(7) Uani d . 1
H H44 0.2419 -0.0067 0.1722 0.051 Uiso calc R 1
C C5 0.30481(17) 0.2698(5) 0.1325(2) 0.0367(6) Uani d . 1
C C6 0.37377(17) 0.4209(5) 0.1696(2) 0.0339(6) Uani d . 1
C C7 0.49894(18) 0.5409(5) 0.3167(2) 0.0375(6) Uani d . 1
H H13 0.5301 0.5190 0.3874 0.045 Uiso calc R 1
C C8 0.64752(17) 0.8427(5) 0.3996(2) 0.0369(6) Uani d . 1
C C9 0.61215(17) 1.0237(5) 0.2381(2) 0.0367(6) Uani d . 1
C C10 0.5679(2) 1.0718(6) 0.1242(2) 0.0463(7) Uani d . 1
H H15A 0.5240 0.9595 0.1009 0.069 Uiso calc R 1
H H15B 0.6172 1.0821 0.0718 0.069 Uiso calc R 1
H H15C 0.5338 1.2049 0.1259 0.069 Uiso calc R 1
N N1 0.52117(14) 0.7007(4) 0.25680(18) 0.0346(5) Uani d . 1
N N2 0.58991(14) 0.8440(4) 0.29821(17) 0.0347(5) Uani d . 1
N N3 0.69709(17) 1.0251(5) 0.3919(2) 0.0441(6) Uani d . 1
H H3 0.7380 1.0693 0.4442 0.053 Uiso calc R 1
N N4 0.67653(16) 1.1360(5) 0.2924(2) 0.0436(6) Uani d . 1
O O1 0.38826(15) 0.5879(4) 0.09998(18) 0.0464(6) Uani d . 1
O O2 0.25821(14) 0.3108(4) 0.03004(16) 0.0478(6) Uani d . 1
H H2 0.2197 0.2146 0.0141 0.072 Uiso calc R 1
O O3 0.64859(14) 0.7078(4) 0.47417(16) 0.0471(5) Uani d . 1
H H1 0.438(3) 0.656(9) 0.131(4) 0.074(13) Uiso d . 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.0356(12) 0.0356(15) 0.0357(12) -0.0006(11) -0.0031(10) -0.0023(12)
C2 0.0501(15) 0.0436(17) 0.0362(13) -0.0019(14) -0.0062(11) 0.0060(14)
C3 0.0557(16) 0.0408(17) 0.0446(15) -0.0055(14) 0.0084(12) 0.0037(13)
C4 0.0385(13) 0.0375(15) 0.0507(16) -0.0066(12) 0.0007(11) -0.0069(13)
C5 0.0301(11) 0.0395(16) 0.0396(13) 0.0018(11) -0.0040(10) -0.0078(11)
C6 0.0325(11) 0.0311(13) 0.0371(12) 0.0012(11) -0.0041(9) -0.0008(11)
C7 0.0393(12) 0.0398(16) 0.0322(11) 0.0013(12) -0.0072(9) -0.0004(12)
C8 0.0327(11) 0.0408(14) 0.0354(12) 0.0039(11) -0.0101(9) -0.0046(12)
C9 0.0360(12) 0.0369(14) 0.0365(12) 0.0004(11) -0.0031(9) 0.0007(12)
C10 0.0431(14) 0.0524(19) 0.0420(14) -0.0001(13) -0.0081(11) 0.0084(14)
N1 0.0334(10) 0.0329(12) 0.0360(10) -0.0011(9) -0.0096(8) -0.0030(10)
N2 0.0326(10) 0.0359(12) 0.0339(10) -0.0007(9) -0.0107(8) -0.0002(10)
N3 0.0433(11) 0.0432(14) 0.0431(12) -0.0087(11) -0.0172(9) -0.0034(12)
N4 0.0402(11) 0.0448(14) 0.0445(12) -0.0061(11) -0.0077(9) 0.0013(12)
O1 0.0493(11) 0.0393(12) 0.0472(11) -0.0091(10) -0.0206(9) 0.0101(9)
O2 0.0463(10) 0.0471(13) 0.0470(12) -0.0054(10) -0.0183(9) -0.0041(10)
O3 0.0477(10) 0.0514(13) 0.0392(10) -0.0007(10) -0.0178(8) 0.0063(10)
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
C6 C1 C2 118.7(2)
C6 C1 C7 122.7(2)
C2 C1 C7 118.6(2)
C3 C2 C1 121.1(3)
C3 C2 H8 119.5
C1 C2 H8 119.5
C2 C3 C4 120.0(3)
C2 C3 H9 120.0
C4 C3 H9 120.0
C5 C4 C3 120.3(3)
C5 C4 H44 119.9
C3 C4 H44 119.9
O2 C5 C4 124.1(2)
O2 C5 C6 115.5(3)
C4 C5 C6 120.4(2)
O1 C6 C1 123.3(2)
O1 C6 C5 117.1(2)
C1 C6 C5 119.6(3)
N1 C7 C1 119.7(2)
N1 C7 H13 120.2
C1 C7 H13 120.2
O3 C8 N3 131.0(2)
O3 C8 N2 127.2(3)
N3 C8 N2 101.8(2)
N4 C9 N2 111.1(2)
N4 C9 C10 125.8(3)
N2 C9 C10 123.0(3)
C9 C10 H15A 109.5
C9 C10 H15B 109.5
H15A C10 H15B 109.5
C9 C10 H15C 109.5
H15A C10 H15C 109.5
H15B C10 H15C 109.5
C7 N1 N2 119.9(2)
N1 N2 C9 121.4(2)
N1 N2 C8 130.3(2)
C9 N2 C8 108.3(2)
C8 N3 N4 114.0(2)
C8 N3 H3 123.0
N4 N3 H3 123.0
C9 N4 N3 104.7(2)
C6 O1 H1 105(3)
C5 O2 H2 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.396(4)
C1 C2 1.407(4)
C1 C7 1.453(4)
C2 C3 1.367(4)
C2 H8 0.9300
C3 C4 1.386(4)
C3 H9 0.9300
C4 C5 1.377(4)
C4 H44 0.9300
C5 O2 1.365(3)
C5 C6 1.398(4)
C6 O1 1.356(3)
C7 N1 1.277(4)
C7 H13 0.9300
C8 O3 1.223(4)
C8 N3 1.340(4)
C8 N2 1.402(3)
C9 N4 1.280(4)
C9 N2 1.378(4)
C9 C10 1.480(4)
C10 H15A 0.9600
C10 H15B 0.9600
C10 H15C 0.9600
N1 N2 1.379(3)
N3 N4 1.384(4)
N3 H3 0.8600
O1 H1 0.87(5)
O2 H2 0.8200
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
O2 H2 O1 4_545 0.82 2.11 2.842(3) 148.4
N3 H3 O3 4_656 0.86 2.00 2.830(3) 162.9
O1 H1 N1 . 0.87(5) 1.85(5) 2.634(3) 148(4)
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
C6 C1 C2 C3 0.2(4)
C7 C1 C2 C3 -178.2(3)
C1 C2 C3 C4 -0.2(5)
C2 C3 C4 C5 -0.1(4)
C3 C4 C5 O2 -179.6(3)
C3 C4 C5 C6 0.5(4)
C2 C1 C6 O1 -179.0(2)
C7 C1 C6 O1 -0.7(4)
C2 C1 C6 C5 0.2(4)
C7 C1 C6 C5 178.5(2)
O2 C5 C6 O1 -1.2(4)
C4 C5 C6 O1 178.7(2)
O2 C5 C6 C1 179.5(2)
C4 C5 C6 C1 -0.5(4)
C6 C1 C7 N1 -1.6(4)
C2 C1 C7 N1 176.7(3)
C1 C7 N1 N2 178.4(2)
C7 N1 N2 C9 -176.8(2)
C7 N1 N2 C8 3.3(4)
N4 C9 N2 N1 179.0(2)
C10 C9 N2 N1 -2.6(4)
N4 C9 N2 C8 -1.1(3)
C10 C9 N2 C8 177.3(3)
O3 C8 N2 N1 0.5(5)
N3 C8 N2 N1 -178.5(3)
O3 C8 N2 C9 -179.4(3)
N3 C8 N2 C9 1.6(3)
O3 C8 N3 N4 179.4(3)
N2 C8 N3 N4 -1.7(3)
N2 C9 N4 N3 0.0(3)
C10 C9 N4 N3 -178.3(3)
C8 N3 N4 C9 1.1(3)