#------------------------------------------------------------------------------
#$Date: 2011-09-17 21:27:16 +0100 (Sat, 17 Sep 2011) $
#$Revision: 26029 $
#$URL: svn://www.crystallography.net/cod/cif/2/2202563.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_2202563
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2003
_journal_volume  59
_journal_page_first  o1535
_journal_page_last  o1537
_publ_section_title
;
3-Phenyl-5-p-tolyl-4-(3,4,5-trimethoxybenzylamino)-4H-1,2,4-triazole
;
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_[local]_cod_cif_authors_sg_H-M  'P 21/n'
loop_
_publ_author_name
  '\,Samil I\,s\?ik'
  'B. Can Olcay'
  'Ay\,sen A\~gar'
  'Selami \,Sa\,smaz'
_chemical_formula_moiety  'C25 H25 N4 O3'
_chemical_formula_sum  'C25 H25 N4 O3'
_chemical_formula_iupac  'C25 H25 N4 O3'
_chemical_formula_weight  430.51
_symmetry_cell_setting  'monoclinic'
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'
_cell_length_a  13.2141(9)
_cell_length_b  9.8945(5)
_cell_length_c  17.8861(12)
_cell_angle_alpha  90.00
_cell_angle_beta  97.336(5)
_cell_angle_gamma  90.00
_cell_volume  2319.4(3)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.233
_diffrn_ambient_temperature  293
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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
  O2 0.25690(13) 0.16742(16) 0.48652(10) 0.0744(5) Uani d . 1 . . O
  N4 0.62928(15) 0.45658(17) 0.68185(11) 0.0607(5) Uani d . 1 . . N
  C22 0.52370(17) 0.2735(2) 0.51896(13) 0.0608(6) Uani d . 1 . . C
  H22 0.5864 0.2493 0.5045 0.073 Uiso calc R 1 . . H
  N1 0.63392(15) 0.32612(17) 0.71356(10) 0.0615(5) Uani d . 1 . . N
  C18 0.42537(17) 0.4140(2) 0.59168(12) 0.0591(6) Uani d . 1 . . C
  H18 0.4218 0.4849 0.6254 0.071 Uiso calc R 1 . . H
  C19 0.33795(17) 0.3437(2) 0.56356(12) 0.0595(6) Uani d . 1 . . C
  O1 0.24276(13) 0.3728(2) 0.58098(11) 0.0835(6) Uani d . 1 . . O
  C2 0.6967(2) 0.2220(2) 0.70312(14) 0.0677(7) Uani d . 1 . . C
  C16 0.61322(17) 0.4546(2) 0.59876(13) 0.0604(6) Uani d . 1 . . C
  H16A 0.6717 0.4129 0.5803 0.073 Uiso calc R 1 . . H
  H16B 0.6078 0.5466 0.5800 0.073 Uiso calc R 1 . . H
  C17 0.51815(17) 0.3777(2) 0.56914(12) 0.0551(5) Uani d . 1 . . C
  C20 0.34343(17) 0.2381(2) 0.51345(12) 0.0607(6) Uani d . 1 . . C
  O3 0.43324(16) 0.10241(19) 0.43842(12) 0.0876(6) Uani d . 1 . . O
  N2 0.6684(2) 0.1144(2) 0.73602(14) 0.0869(8) Uani d . 1 . . N
  C9 0.7788(2) 0.2302(2) 0.65563(15) 0.0733(8) Uani d . 1 . . C
  C21 0.43630(19) 0.2045(2) 0.48992(13) 0.0636(6) Uani d . 1 . . C
  C14 0.7786(2) 0.1369(3) 0.59801(17) 0.0802(8) Uani d . 1 . . C
  H14 0.7306 0.0677 0.5926 0.096 Uiso calc R 1 . . H
  C1 0.5619(2) 0.2733(2) 0.75425(13) 0.0717(7) Uani d . 1 . . C
  C3 0.4748(2) 0.3446(3) 0.77930(14) 0.0728(7) Uani d . 1 . . C
  N3 0.5824(2) 0.1469(2) 0.76896(14) 0.0860(7) Uani d . 1 . . N
  C10 0.8525(2) 0.3299(3) 0.66486(17) 0.0783(8) Uani d . 1 . . C
  H10 0.8549 0.3901 0.7050 0.094 Uiso calc R 1 . . H
  C24 0.2068(2) 0.2208(3) 0.41775(16) 0.0879(9) Uani d . 1 . . C
  H24A 0.1881 0.3131 0.4252 0.132 Uiso calc R 1 . . H
  H24B 0.1466 0.1687 0.4019 0.132 Uiso calc R 1 . . H
  H24C 0.2520 0.2166 0.3798 0.132 Uiso calc R 1 . . H
  C8 0.4784(2) 0.4780(3) 0.80062(16) 0.0865(8) Uani d . 1 . . C
  H8 0.5377 0.5276 0.7981 0.104 Uiso calc R 1 . . H
  C11 0.9219(3) 0.3394(3) 0.6148(2) 0.0962(10) Uani d . 1 . . C
  H11 0.9702 0.4083 0.6200 0.115 Uiso calc R 1 . . H
  C13 0.8485(3) 0.1475(3) 0.5499(2) 0.0937(10) Uani d . 1 . . C
  H13 0.8470 0.0846 0.5111 0.112 Uiso calc R 1 . . H
  C12 0.9211(2) 0.2451(4) 0.55498(19) 0.0934(9) Uani d . 1 . . C
  C7 0.3953(3) 0.5391(4) 0.8257(2) 0.1018(10) Uani d . 1 . . C
  H7 0.3993 0.6294 0.8402 0.122 Uiso calc R 1 . . H
  C25 0.5190(3) 0.0838(4) 0.3990(2) 0.1072(11) Uani d . 1 . . C
  H25A 0.5337 0.1668 0.3747 0.161 Uiso calc R 1 . . H
  H25B 0.5044 0.0143 0.3618 0.161 Uiso calc R 1 . . H
  H25C 0.5770 0.0579 0.4340 0.161 Uiso calc R 1 . . H
  C23 0.2293(2) 0.4968(4) 0.6155(2) 0.1058(11) Uani d . 1 . . C
  H23A 0.2643 0.4957 0.6660 0.159 Uiso calc R 1 . . H
  H23B 0.1579 0.5123 0.6170 0.159 Uiso calc R 1 . . H
  H23C 0.2566 0.5677 0.5874 0.159 Uiso calc R 1 . . H
  C15 0.9943(3) 0.2586(6) 0.5039(3) 0.1458(17) Uani d . 1 . . C
  H15A 0.9710 0.2111 0.4581 0.219 Uiso calc R 1 . . H
  H15B 1.0582 0.2213 0.5260 0.219 Uiso calc R 1 . . H
  H15C 1.0031 0.3525 0.4929 0.219 Uiso calc R 1 . . H
  C6 0.3059(3) 0.4683(5) 0.8297(2) 0.1191(13) Uani d . 1 . . C
  H6 0.2496 0.5098 0.8462 0.143 Uiso calc R 1 . . H
  C4 0.3851(3) 0.2734(4) 0.7833(2) 0.1094(12) Uani d . 1 . . C
  H4 0.3804 0.1831 0.7687 0.131 Uiso calc R 1 . . H
  C5 0.3031(3) 0.3367(6) 0.8089(3) 0.1358(17) Uani d . 1 . . C
  H5 0.2439 0.2874 0.8119 0.163 Uiso calc R 1 . . H
  H4N 0.6789(18) 0.498(2) 0.7003(13) 0.058(7) Uiso d . 1 . . H
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
  O2 0.0726(10) 0.0734(10) 0.0704(10) -0.0228(8) -0.0170(8) 0.0003(8)
  N4 0.0663(12) 0.0408(8) 0.0680(12) -0.0070(8) -0.0189(9) 0.0044(8)
  C22 0.0616(13) 0.0562(12) 0.0609(13) 0.0027(10) -0.0071(10) 0.0054(10)
  N1 0.0741(12) 0.0462(9) 0.0559(10) -0.0023(9) -0.0232(9) 0.0039(8)
  C18 0.0633(14) 0.0561(12) 0.0531(12) -0.0043(10) -0.0106(10) 0.0006(9)
  C19 0.0571(13) 0.0660(13) 0.0519(12) -0.0062(10) -0.0062(10) 0.0035(10)
  O1 0.0602(11) 0.1040(14) 0.0845(12) -0.0097(9) 0.0027(9) -0.0231(11)
  C2 0.0825(16) 0.0505(12) 0.0620(14) 0.0007(11) -0.0217(12) -0.0002(10)
  C16 0.0605(12) 0.0536(11) 0.0622(13) -0.0038(9) -0.0114(10) 0.0132(10)
  C17 0.0611(13) 0.0494(10) 0.0499(11) -0.0035(9) -0.0115(9) 0.0122(9)
  C20 0.0676(14) 0.0544(12) 0.0544(12) -0.0112(10) -0.0141(10) 0.0055(10)
  O3 0.0951(14) 0.0739(11) 0.0887(13) -0.0013(10) -0.0074(11) -0.0266(10)
  N2 0.122(2) 0.0501(11) 0.0776(14) -0.0038(12) -0.0274(14) 0.0154(10)
  C9 0.0883(17) 0.0445(11) 0.0757(16) 0.0110(11) -0.0331(14) -0.0088(11)
  C21 0.0740(15) 0.0516(12) 0.0601(13) 0.0000(10) -0.0113(11) 0.0003(10)
  C14 0.0867(19) 0.0688(15) 0.0784(18) 0.0085(14) -0.0154(15) -0.0112(13)
  C1 0.0953(18) 0.0580(13) 0.0538(13) -0.0216(13) -0.0209(12) 0.0162(10)
  C3 0.0805(17) 0.0750(16) 0.0576(13) -0.0075(13) -0.0120(12) 0.0160(12)
  N3 0.1095(19) 0.0677(14) 0.0755(15) -0.0045(13) -0.0083(14) 0.0185(11)
  C10 0.0756(17) 0.0673(15) 0.0882(19) 0.0058(12) -0.0036(15) -0.0190(13)
  C24 0.0788(17) 0.102(2) 0.0744(17) -0.0102(15) -0.0242(14) -0.0024(15)
  C8 0.0842(19) 0.096(2) 0.0724(17) -0.0120(16) -0.0156(14) 0.0001(15)
  C11 0.085(2) 0.0848(19) 0.114(3) 0.0015(15) -0.0061(19) -0.0155(18)
  C13 0.096(2) 0.0820(19) 0.094(2) 0.0068(16) -0.0239(18) -0.0206(16)
  C12 0.0733(18) 0.122(3) 0.085(2) 0.0187(18) 0.0107(15) 0.0006(18)
  C7 0.086(2) 0.117(3) 0.098(2) 0.005(2) -0.0085(18) -0.003(2)
  C25 0.123(3) 0.102(2) 0.099(2) 0.006(2) 0.020(2) -0.0332(19)
  C23 0.0744(19) 0.126(3) 0.115(3) 0.0066(18) 0.0064(17) -0.032(2)
  C15 0.100(3) 0.203(5) 0.135(3) -0.007(3) 0.016(3) -0.004(4)
  C6 0.122(3) 0.126(3) 0.104(3) -0.008(3) -0.003(2) 0.035(2)
  C4 0.124(3) 0.092(2) 0.110(3) -0.034(2) 0.005(2) 0.0335(19)
  C5 0.093(3) 0.162(4) 0.158(4) -0.013(3) 0.037(3) 0.056(3)
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
  O2 C20 . 1.374(2) ?
  O2 C24 . 1.422(3) ?
  N4 N1 . 1.408(2) yes
  N4 C16 . 1.474(3) yes
  N4 H4N . 0.81(2) ?
  C22 C17 . 1.375(3) ?
  C22 C21 . 1.384(3) ?
  C22 H22 . 0.9300 ?
  N1 C2 . 1.351(3) yes
  N1 C1 . 1.373(3) yes
  C18 C17 . 1.386(3) ?
  C18 C19 . 1.387(3) ?
  C18 H18 . 0.9300 ?
  C19 O1 . 1.365(3) ?
  C19 C20 . 1.385(3) ?
  O1 C23 . 1.395(4) ?
  C2 N2 . 1.295(3) yes
  C2 C9 . 1.462(4) ?
  C16 C17 . 1.506(3) ?
  C16 H16A . 0.9700 ?
  C16 H16B . 0.9700 ?
  C20 C21 . 1.388(4) ?
  O3 C21 . 1.365(3) ?
  O3 C25 . 1.421(4) ?
  N2 N3 . 1.382(4) yes
  C9 C10 . 1.382(4) ?
  C9 C14 . 1.383(4) ?
  C14 C13 . 1.346(5) ?
  C14 H14 . 0.9300 ?
  C1 N3 . 1.300(3) yes
  C1 C3 . 1.468(4) ?
  C3 C8 . 1.372(4) ?
  C3 C4 . 1.388(4) ?
  C10 C11 . 1.364(5) ?
  C10 H10 . 0.9300 ?
  C24 H24A . 0.9600 ?
  C24 H24B . 0.9600 ?
  C24 H24C . 0.9600 ?
  C8 C7 . 1.379(5) ?
  C8 H8 . 0.9300 ?
  C11 C12 . 1.419(5) ?
  C11 H11 . 0.9300 ?
  C13 C12 . 1.356(5) ?
  C13 H13 . 0.9300 ?
  C12 C15 . 1.419(5) ?
  C7 C6 . 1.382(5) ?
  C7 H7 . 0.9300 ?
  C25 H25A . 0.9600 ?
  C25 H25B . 0.9600 ?
  C25 H25C . 0.9600 ?
  C23 H23A . 0.9600 ?
  C23 H23B . 0.9600 ?
  C23 H23C . 0.9600 ?
  C15 H15A . 0.9600 ?
  C15 H15B . 0.9600 ?
  C15 H15C . 0.9600 ?
  C6 C5 . 1.353(6) ?
  C6 H6 . 0.9300 ?
  C4 C5 . 1.380(6) ?
  C4 H4 . 0.9300 ?
  C5 H5 . 0.9300 ?
_cod_database_code 2202563