#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/62/2206269.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_2206269
loop_
_publ_author_name
'Zuo-Xiang Wang'
'Yan Lan'
'Lu-Tong Yuan'
'Chun-Yi Liu'
_publ_section_title
;
 4-(4-Methoxyphenyl)-3-methyl-5-(2-pyridyl)-4H-1,2,4-triazole
 dihydrate
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2033
_journal_page_last               o2034
_journal_paper_doi               10.1107/S1600536805017137
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C15 H14 N4 O, 2H2 O'
_chemical_formula_moiety         'C15 H14 N4 O, 2H2 O'
_chemical_formula_sum            'C15 H18 N4 O3'
_chemical_formula_weight         302.33
_chemical_name_systematic
;
4-(4-Methoxyphenyl)-3-methyl-5-(2-pyridyl)-4H-1,2,4-triazole dihydrate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.897(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.629(3)
_cell_length_b                   9.927(2)
_cell_length_c                   14.019(3)
_cell_measurement_reflns_used    793
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      25.12
_cell_measurement_theta_min      3.06
_cell_volume                     1548.5(6)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 2000)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_sigmaI/netI    0.0435
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7967
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.55
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.129
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3038
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.968
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0482
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0683P)²+0.0126P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1148
_reflns_number_gt                2217
_reflns_number_total             3038
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz6085.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2206269
_cod_database_fobs_code          2206269
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_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_type_symbol
C1 0.22833(15) 1.02561(18) 0.00021(12) 0.0352(4) Uani d . 1 C
C2 0.14031(17) 1.08828(18) -0.07416(12) 0.0393(4) Uani d . 1 C
H2 0.0675 1.1121 -0.0638 0.047 Uiso calc R 1 H
C3 0.16146(16) 1.11542(18) -0.16445(13) 0.0397(4) Uani d . 1 C
H3 0.1031 1.1579 -0.2152 0.048 Uiso calc R 1 H
C4 0.26977(17) 1.07894(18) -0.17843(13) 0.0404(4) Uani d . 1 C
H4 0.2858 1.0968 -0.2384 0.048 Uiso calc R 1 H
C5 0.35391(17) 1.01550(19) -0.10162(13) 0.0397(4) Uani d . 1 C
H5 0.4266 0.9906 -0.1117 0.048 Uiso d R 1 H
C6 0.21045(15) 0.99934(17) 0.09708(12) 0.0340(4) Uani d . 1 C
C7 0.20174(15) 0.90787(17) 0.23488(12) 0.0349(4) Uani d . 1 C
C8 0.30703(15) 0.76918(17) 0.13809(12) 0.0344(4) Uani d . 1 C
C9 0.24634(16) 0.66852(17) 0.07924(12) 0.0363(4) Uani d . 1 C
H9 0.1647 0.6788 0.0473 0.044 Uiso calc R 1 H
C10 0.30350(15) 0.55065(17) 0.06571(13) 0.0364(4) Uani d . 1 C
H10 0.2606 0.4819 0.0258 0.044 Uiso calc R 1 H
C11 0.42424(16) 0.53663(18) 0.11190(13) 0.0389(4) Uani d . 1 C
C12 0.48557(16) 0.63860(17) 0.17119(13) 0.0365(4) Uani d . 1 C
H12 0.5673 0.6287 0.2029 0.044 Uiso calc R 1 H
C13 0.42917(15) 0.75344(17) 0.18435(13) 0.0354(4) Uani d . 1 C
H13 0.4723 0.8218 0.2244 0.043 Uiso calc R 1 H
C14 0.21062(16) 0.80429(18) 0.31344(12) 0.0360(4) Uani d . 1 C
H14A 0.1651 0.8329 0.3570 0.054 Uiso calc R 1 H
H14B 0.2933 0.7928 0.3512 0.054 Uiso calc R 1 H
H14C 0.1792 0.7203 0.2828 0.054 Uiso calc R 1 H
C15 0.42748(17) 0.31490(18) 0.04835(14) 0.0409(4) Uani d . 1 C
H15A 0.3825 0.2709 0.0869 0.061 Uiso calc R 1 H
H15B 0.4842 0.2527 0.0352 0.061 Uiso calc R 1 H
H15C 0.3736 0.3453 -0.0136 0.061 Uiso calc R 1 H
N1 0.24568(13) 0.88606(15) 0.15523(10) 0.0346(3) Uani d . 1 N
N2 0.15425(14) 1.08210(15) 0.13926(11) 0.0390(4) Uani d . 1 N
N3 0.14852(13) 1.02171(15) 0.22771(10) 0.0384(3) Uani d . 1 N
N4 0.33564(12) 0.98628(14) -0.01134(10) 0.0352(3) Uani d . 1 N
O1 0.48953(11) 0.42649(12) 0.10208(9) 0.0416(3) Uani d . 1 O
O2 0.02270(14) 0.08536(13) 0.37332(11) 0.0545(4) Uani d . 1 O
H2D 0.0293 0.1283 0.3227 0.065 Uiso d R 1 H
H2C 0.0233 0.1406 0.4198 0.082 Uiso d R 1 H
O3 0.06182(14) 0.34200(13) 0.07192(11) 0.0527(4) Uani d . 1 O
H3B 0.1137 0.3079 0.1218 0.063 Uiso d R 1 H
H3C -0.0066 0.3420 0.0825 0.063 Uiso d R 1 H
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
_geom_angle_publ_flag
N4 C1 C2 122.96(16) ?
N4 C1 C6 116.36(15) ?
C2 C1 C6 120.68(16) ?
C1 C2 C3 119.28(17) ?
C1 C2 H2 120.4 ?
C3 C2 H2 120.4 ?
C4 C3 C2 119.44(17) ?
C4 C3 H3 120.3 ?
C2 C3 H3 120.3 ?
C3 C4 C5 118.65(17) ?
C3 C4 H4 120.7 ?
C5 C4 H4 120.7 ?
N4 C5 C4 123.45(17) ?
N4 C5 H5 118.3 ?
C4 C5 H5 118.2 ?
N2 C6 N1 110.48(14) yes
N2 C6 C1 122.70(15) yes
N1 C6 C1 126.79(15) yes
N3 C7 N1 111.19(15) yes
N3 C7 C14 126.65(15) yes
N1 C7 C14 122.04(15) yes
C9 C8 C13 118.83(16) ?
C9 C8 N1 120.48(15) ?
C13 C8 N1 120.63(15) ?
C8 C9 C10 121.33(16) ?
C8 C9 H9 119.3 ?
C10 C9 H9 119.3 ?
C11 C10 C9 119.14(16) ?
C11 C10 H10 120.4 ?
C9 C10 H10 120.4 ?
O1 C11 C12 116.57(15) ?
O1 C11 C10 123.95(16) ?
C12 C11 C10 119.47(17) ?
C13 C12 C11 121.12(17) ?
C13 C12 H12 119.4 ?
C11 C12 H12 119.4 ?
C12 C13 C8 120.09(16) ?
C12 C13 H13 120.0 ?
C8 C13 H13 120.0 ?
C7 C14 H14A 109.5 ?
C7 C14 H14B 109.5 ?
H14A C14 H14B 109.5 ?
C7 C14 H14C 109.5 ?
H14A C14 H14C 109.5 ?
H14B C14 H14C 109.5 ?
O1 C15 H15A 109.5 ?
O1 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
O1 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
C7 N1 C6 103.61(14) yes
C7 N1 C8 126.22(14) yes
C6 N1 C8 130.10(14) yes
C6 N2 N3 107.09(14) yes
C7 N3 N2 107.60(14) yes
C1 N4 C5 116.21(15) ?
C11 O1 C15 118.03(14) ?
H2D O2 H2C 109.5 ?
H3B O3 H3C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N4 1.361(2) ?
C1 C2 1.379(2) ?
C1 C6 1.456(2) ?
C2 C3 1.384(2) ?
C2 H2 0.9300 ?
C3 C4 1.378(3) ?
C3 H3 0.9300 ?
C4 C5 1.379(3) ?
C4 H4 0.9300 ?
C5 N4 1.374(2) ?
C5 H5 0.9300 ?
C6 N2 1.295(2) yes
C6 N1 1.379(2) yes
C7 N3 1.278(2) yes
C7 N1 1.374(2) yes
C7 C14 1.488(2) ?
C8 C9 1.356(2) ?
C8 C13 1.388(2) ?
C8 N1 1.419(2) ?
C9 C10 1.386(2) ?
C9 H9 0.9300 ?
C10 C11 1.372(3) ?
C10 H10 0.9300 ?
C11 O1 1.361(2) yes
C11 C12 1.371(2) ?
C12 C13 1.354(2) ?
C12 H12 0.9300 ?
C13 H13 0.9300 ?
C14 H14A 0.9600 ?
C14 H14B 0.9600 ?
C14 H14C 0.9600 ?
C15 O1 1.414(2) yes
C15 H15A 0.9600 ?
C15 H15B 0.9600 ?
C15 H15C 0.9600 ?
N2 N3 1.396(2) yes
O2 H2D 0.8500 ?
O2 H2C 0.8500 ?
O3 H3B 0.8500 ?
O3 H3C 0.8501 ?
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 H2D N3 1_545 0.85 2.43 2.906(2) 116
O3 H3B N2 1_545 0.85 2.29 2.848(2) 124
O2 H2C O3 4_566 0.85 2.06 2.783(2) 143
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21129224
