#------------------------------------------------------------------------------
#$Date: 2015-09-27 04:15:54 +0300 (Sun, 27 Sep 2015) $
#$Revision: 158433 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/11/2241165.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_2241165
loop_
_publ_author_name
'Khazhieva, Inna S.'
'Glukhareva, Tatiana V.'
'Slepukhin, Pavel A.'
'Morzherin, Yury Yu.'
_publ_section_title
;
 Crystal structure of
 1-methoxy-5-methyl-N-phenyl-1.2.3-triazole-4-carboxamide
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o798
_journal_paper_doi               10.1107/S2056989015017776
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C11 H12 N4 O2'
_chemical_formula_moiety         'C11 H12 N4 O2'
_chemical_formula_sum            'C11 H12 N4 O2'
_chemical_formula_weight         232.25
_chemical_melting_point          310
_chemical_name_systematic
;
1-Methoxy-5-methyl-N-phenyl-triazole-4-carboxamide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           Olex2
_cell_angle_alpha                90.00
_cell_angle_beta                 100.367(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.4637(8)
_cell_length_b                   6.4345(13)
_cell_length_c                   15.822(3)
_cell_measurement_reflns_used    1077
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.42
_cell_measurement_theta_min      2.90
_cell_volume                     1148.0(3)
_computing_cell_refinement
;
CrysAlis Pro (Agilent, 2006)
;
_computing_data_collection
;
CrysAlis Pro (Agilent, 2006)
;
_computing_data_reduction
;
CrysAlis Pro (Agilent, 2006)
;
_computing_molecular_graphics
;
publCIF (Westrip, 2010)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXS97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS-97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Agilent Xcalibur S CCD'
_diffrn_measurement_method       'omega scans'
_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  0.0400
_diffrn_reflns_av_sigmaI/netI    0.0684
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7259
_diffrn_reflns_theta_full        26.42
_diffrn_reflns_theta_max         26.42
_diffrn_reflns_theta_min         2.90
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.222
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2302
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.1296
_refine_ls_R_factor_gt           0.0547
_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)+(0.0682P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1319
_refine_ls_wR_factor_ref         0.1474
_reflns_number_gt                1077
_reflns_number_total             2302
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb7511sup1.cif
_cod_data_source_block           I
_cod_database_code               2241165
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
O O1 0.61315(16) 0.0563(3) 0.15704(14) 0.0777(7) Uani d . 1 1
C C8 0.7887(2) 0.1712(4) 0.24262(18) 0.0475(7) Uani d . 1 1
C C6 0.7399(2) -0.2566(4) 0.08075(18) 0.0496(7) Uani d . 1 1
C C7 0.7204(2) 0.0365(4) 0.17728(19) 0.0533(7) Uani d . 1 1
N N2 0.90562(18) 0.1400(4) 0.27423(17) 0.0605(7) Uani d . 1 1
N N4 0.8463(2) 0.3915(4) 0.33811(19) 0.0708(8) Uani d . 1 1
C C9 0.7489(2) 0.3375(4) 0.28291(19) 0.0553(8) Uani d . 1 1
N N1 0.7844(2) -0.1083(4) 0.14353(16) 0.0530(6) Uani d . 1 1
N N3 0.9416(2) 0.2771(4) 0.3343(2) 0.0759(8) Uani d . 1 1
O O2 0.8515(2) 0.5302(4) 0.40535(18) 0.0956(8) Uani d . 1 1
C C1 0.7975(2) -0.4450(5) 0.0824(2) 0.0589(8) Uani d . 1 1
H H1A 0.8634 -0.4721 0.1246 0.071 Uiso calc R 1 1
C C5 0.6434(3) -0.2172(5) 0.0169(2) 0.0641(8) Uani d . 1 1
H H5A 0.6049 -0.0896 0.0148 0.077 Uiso calc R 1 1
C C3 0.6605(3) -0.5520(6) -0.0411(2) 0.0809(10) Uani d . 1 1
H H3A 0.6331 -0.6524 -0.0821 0.097 Uiso calc R 1 1
C C2 0.7571(3) -0.5924(5) 0.0214(2) 0.0739(9) Uani d . 1 1
H H2A 0.7955 -0.7200 0.0225 0.089 Uiso calc R 1 1
C C4 0.6048(3) -0.3651(6) -0.0430(2) 0.0769(10) Uani d . 1 1
H H4A 0.5395 -0.3381 -0.0857 0.092 Uiso calc R 1 1
C C11 0.9070(4) 0.7045(6) 0.3901(3) 0.137(2) Uani d . 1 1
H H11A 0.8970 0.8073 0.4321 0.205 Uiso calc R 1 1
H H11B 0.8741 0.7551 0.3337 0.205 Uiso calc R 1 1
H H11C 0.9900 0.6765 0.3933 0.205 Uiso calc R 1 1
C C10 0.6343(3) 0.4512(5) 0.2740(2) 0.0818(10) Uani d . 1 1
H H10A 0.6298 0.5214 0.3268 0.123 Uiso calc R 1 1
H H10B 0.5699 0.3543 0.2609 0.123 Uiso calc R 1 1
H H10C 0.6292 0.5511 0.2284 0.123 Uiso calc R 1 1
H H1 0.858(2) -0.109(4) 0.1666(17) 0.048(8) Uiso d . 1 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
N2 C8 C9 109.5(2)
N2 C8 C7 122.6(2)
C9 C8 C7 127.8(2)
C1 C6 C5 119.6(3)
C1 C6 N1 118.1(3)
C5 C6 N1 122.3(3)
O1 C7 N1 124.1(3)
O1 C7 C8 120.6(2)
N1 C7 C8 115.3(2)
N3 N2 C8 109.2(2)
N3 N4 C9 115.2(2)
N3 N4 O2 118.1(3)
C9 N4 O2 125.9(2)
N4 C9 C8 101.5(2)
N4 C9 C10 123.7(3)
C8 C9 C10 134.8(3)
C7 N1 C6 126.3(3)
C7 N1 H1 113.4(17)
C6 N1 H1 120.2(17)
N2 N3 N4 104.6(2)
C11 O2 N4 111.1(3)
C2 C1 C6 119.6(3)
C2 C1 H1A 120.2
C6 C1 H1A 120.2
C4 C5 C6 120.0(3)
C4 C5 H5A 120.0
C6 C5 H5A 120.0
C4 C3 C2 120.0(3)
C4 C3 H3A 120.0
C2 C3 H3A 120.0
C3 C2 C1 120.2(3)
C3 C2 H2A 119.9
C1 C2 H2A 119.9
C5 C4 C3 120.7(3)
C5 C4 H4A 119.6
C3 C4 H4A 119.6
O2 C11 H11A 109.5
O2 C11 H11B 109.5
H11A C11 H11B 109.5
O2 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
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
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.220(3)
C8 N2 1.359(3)
C8 C9 1.365(3)
C8 C7 1.463(4)
C6 C1 1.379(4)
C6 C5 1.381(4)
C6 N1 1.405(3)
C7 N1 1.354(3)
N2 N3 1.308(3)
N4 N3 1.327(3)
N4 C9 1.334(3)
N4 O2 1.382(3)
C9 C10 1.488(4)
N1 H1 0.85(3)
O2 C11 1.333(4)
C1 C2 1.372(4)
C1 H1A 0.9300
C5 C4 1.359(4)
C5 H5A 0.9300
C3 C4 1.360(5)
C3 C2 1.370(5)
C3 H3A 0.9300
C2 H2A 0.9300
C4 H4A 0.9300
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
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 N2 . 0.86(2) 2.33(3) 2.780(4) 113(2)
N1 H1 N3 2_745 0.86(2) 2.41(2) 3.184(3) 150(2)

_cod_database_fobs_code 2241165
