##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
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##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
5-(3-Methoxyphenethyl)-4-(2-methoxyphenyl)-4H-1,2,4-triazol-3-ol
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H19 N3 O3'
_chemical_formula_sum     'C18 H19 N3 O3'
_chemical_formula_iupac     'C18 H19 N3 O3'
_chemical_formula_weight     325.36
_chemical_melting_point     454.0(10)
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
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     10.5030(11)
_cell_length_b     14.1172(14)
_cell_length_c     11.3226(11)
_cell_angle_alpha     90.00
_cell_angle_beta     98.192(2)
_cell_angle_gamma     90.00
_cell_volume     1661.7(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9949
_cell_measurement_theta_min     2.43
_cell_measurement_theta_max     28.28
_cell_measurement_temperature     294(2)
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.32
_exptl_crystal_size_mid     0.24
_exptl_crystal_size_min     0.22
_exptl_crystal_density_diffrn     1.301
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     688
_exptl_absorpt_coefficient_mu     0.090
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9016
_exptl_absorpt_correction_T_max     1.0000
_exptl_special_details
;
;
_diffrn_ambient_temperature     294(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART CCD'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     9949
_diffrn_reflns_av_R_equivalents     0.0184
_diffrn_reflns_av_sigmaI/netI     0.0216
_diffrn_reflns_theta_min     2.43
_diffrn_reflns_theta_max     28.28
_diffrn_reflns_theta_full     28.28
_diffrn_measured_fraction_theta_max     0.979
_diffrn_measured_fraction_theta_full     0.979
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     -18
_diffrn_reflns_limit_k_max     18
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     14
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted
R-factor wR and goodness of fit S are based
on F², conventional R-factors R are based
on F, with F set to zero for negative F².
The threshold expression of F² > σ(F²) is used
only for calculating R-factors(gt) etc. and is not
relevant to the choice of reflections for refinement. R-factors
based on F² are statistically about twice as large as those
based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     4026
_reflns_number_gt     3212
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0596
_refine_ls_R_factor_gt     0.0478
_refine_ls_wR_factor_gt     0.1339
_refine_ls_wR_factor_ref     0.1455
_refine_ls_goodness_of_fit_ref     1.017
_refine_ls_restrained_S_all     1.017
_refine_ls_number_reflns     4026
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0854P)²+0.2782P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.559
_refine_diff_density_min     -0.399
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
_computing_data_collection     'SMART (Bruker, 1998)'
_computing_cell_refinement     'SAINT (Bruker, 1999)'
_computing_data_reduction     'SAINT (Bruker, 1999)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
                  'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003)'
_computing_publication_material
                             'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003)'
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
    O O1 0.34683(13) 0.50242(9) 0.80167(14) 0.0726(4) Uani d . 1 . .
    O O2 0.76819(12) 0.19899(8) 0.72362(9) 0.0538(3) Uani d . 1 . .
    O O3 0.99935(9) 0.12807(7) 0.96442(12) 0.0554(3) Uani d . 1 . .
    H H3 1.0436 0.0800 0.9720 0.083 Uiso calc R 1 . .
    N N1 0.78261(10) 0.16861(7) 0.95758(10) 0.0367(2) Uani d . 1 . .
    N N2 0.70357(11) 0.02988(8) 1.00087(11) 0.0439(3) Uani d . 1 . .
    N N3 0.83555(11) 0.02434(8) 0.99977(11) 0.0439(3) Uani d . 1 . .
    C C1 0.4774(2) 0.53003(16) 0.8160(3) 0.0908(8) Uani d . 1 . .
    H H1A 0.4829 0.5979 0.8133 0.136 Uiso calc R 1 . .
    H H1B 0.5180 0.5033 0.7529 0.136 Uiso calc R 1 . .
    H H1C 0.5200 0.5077 0.8915 0.136 Uiso calc R 1 . .
    C C2 0.31961(15) 0.40769(11) 0.80274(13) 0.0485(3) Uani d . 1 . .
    C C3 0.18992(15) 0.38405(12) 0.79300(14) 0.0525(4) Uani d . 1 . .
    H H3A 0.1277 0.4313 0.7837 0.063 Uiso calc R 1 . .
    C C4 0.15417(14) 0.29079(12) 0.79721(14) 0.0512(4) Uani d . 1 . .
    H H4A 0.0675 0.2751 0.7909 0.061 Uiso calc R 1 . .
    C C5 0.24656(13) 0.21925(11) 0.81085(13) 0.0447(3) Uani d . 1 . .
    H H5A 0.2216 0.1563 0.8151 0.054 Uiso calc R 1 . .
    C C6 0.37517(13) 0.24212(10) 0.81805(12) 0.0401(3) Uani d . 1 . .
    C C7 0.41200(14) 0.33670(11) 0.81434(13) 0.0463(3) Uani d . 1 . .
    H H7A 0.4986 0.3523 0.8196 0.056 Uiso calc R 1 . .
    C C8 0.47827(14) 0.16657(11) 0.83435(14) 0.0480(3) Uani d . 1 . .
    H H8A 0.5424 0.1807 0.7831 0.058 Uiso calc R 1 . .
    H H8B 0.4400 0.1059 0.8100 0.058 Uiso calc R 1 . .
    C C9 0.54420(13) 0.15956(10) 0.96390(13) 0.0440(3) Uani d . 1 . .
    H H9A 0.5505 0.2225 0.9987 0.053 Uiso calc R 1 . .
    H H9B 0.4913 0.1214 1.0090 0.053 Uiso calc R 1 . .
    C C10 0.67491(12) 0.11732(9) 0.97478(11) 0.0378(3) Uani d . 1 . .
    C C11 0.88697(13) 0.10760(9) 0.97304(12) 0.0390(3) Uani d . 1 . .
    C C12 0.79093(12) 0.26338(9) 0.91477(12) 0.0374(3) Uani d . 1 . .
    C C13 0.80818(19) 0.33857(12) 0.99299(15) 0.0583(4) Uani d . 1 . .
    H H13A 0.8117 0.3284 1.0746 0.070 Uiso calc R 1 . .
    C C14 0.8202(2) 0.42943(12) 0.94939(19) 0.0751(6) Uani d . 1 . .
    H H14A 0.8323 0.4805 1.0017 0.090 Uiso calc R 1 . .
    C C15 0.8143(2) 0.44367(11) 0.82921(18) 0.0652(5) Uani d . 1 . .
    H H15A 0.8226 0.5048 0.8006 0.078 Uiso calc R 1 . .
    C C16 0.79629(15) 0.36961(11) 0.74987(14) 0.0504(4) Uani d . 1 . .
    H H16A 0.7918 0.3806 0.6684 0.061 Uiso calc R 1 . .
    C C17 0.78478(12) 0.27786(9) 0.79249(12) 0.0386(3) Uani d . 1 . .
    C C18 0.7433(3) 0.21156(16) 0.59719(16) 0.0767(6) Uani d . 1 . .
    H H18A 0.7335 0.1508 0.5590 0.115 Uiso calc R 1 . .
    H H18B 0.8140 0.2447 0.5708 0.115 Uiso calc R 1 . .
    H H18C 0.6659 0.2477 0.5769 0.115 Uiso calc R 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s.
planes) are estimated using the full covariance matrix. The cell
e.s.d.'s are taken into account individually in the estimation of
e.s.d.'s in distances, angles and torsion angles; correlations between
e.s.d.'s in cell parameters are only used when they are defined by
crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s
is used for estimating e.s.d.'s involving l.s. planes.
;
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
    O3 H3 . 0.8200 ?
    N2 N3 . 1.3902(16) ?
    C1 O1 . 1.413(3) ?
    C1 H1A . 0.9600 ?
    C1 H1B . 0.9600 ?
    C1 H1C . 0.9600 ?
    C2 O1 . 1.3680(19) ?
    C2 C7 . 1.388(2) ?
    C2 C3 . 1.391(2) ?
    C3 C4 . 1.372(2) ?
    C3 H3A . 0.9300 ?
    C4 C5 . 1.394(2) ?
    C4 H4A . 0.9300 ?
    C5 C6 . 1.3798(19) ?
    C5 H5A . 0.9300 ?
    C6 C7 . 1.393(2) ?
    C6 C8 . 1.5123(19) ?
    C7 H7A . 0.9300 ?
    C8 C9 . 1.533(2) ?
    C8 H8A . 0.9700 ?
    C8 H8B . 0.9700 ?
    C9 C10 . 1.4857(18) ?
    C9 H9A . 0.9700 ?
    C9 H9B . 0.9700 ?
    C10 N2 . 1.2946(17) ?
    C10 N1 . 1.3801(17) ?
    C11 O3 . 1.2325(16) ?
    C11 N3 . 1.3459(17) ?
    C11 N1 . 1.3854(16) ?
    C12 C13 . 1.378(2) ?
    C12 C17 . 1.3919(18) ?
    C12 N1 . 1.4299(15) ?
    C13 C14 . 1.387(2) ?
    C13 H13A . 0.9300 ?
    C14 C15 . 1.368(3) ?
    C14 H14A . 0.9300 ?
    C15 C16 . 1.374(3) ?
    C15 H15A . 0.9300 ?
    C16 C17 . 1.3934(19) ?
    C16 H16A . 0.9300 ?
    C17 O2 . 1.3563(17) ?
    C18 O2 . 1.429(2) ?
    C18 H18A . 0.9600 ?
    C18 H18B . 0.9600 ?
    C18 H18C . 0.9600 ?
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
    C2 O1 C1 . . 118.00(14) ?
    C17 O2 C18 . . 117.66(13) ?
    C11 O3 H3 . . 109.5 ?
    C10 N1 C11 . . 107.79(10) ?
    C10 N1 C12 . . 129.03(10) ?
    C11 N1 C12 . . 122.62(11) ?
    C10 N2 N3 . . 104.56(11) ?
    C11 N3 N2 . . 112.67(11) ?
    O1 C1 H1A . . 109.5 ?
    O1 C1 H1B . . 109.5 ?
    H1A C1 H1B . . 109.5 ?
    O1 C1 H1C . . 109.5 ?
    H1A C1 H1C . . 109.5 ?
    H1B C1 H1C . . 109.5 ?
    O1 C2 C7 . . 124.22(15) ?
    O1 C2 C3 . . 115.93(14) ?
    C7 C2 C3 . . 119.85(14) ?
    C4 C3 C2 . . 119.81(14) ?
    C4 C3 H3A . . 120.1 ?
    C2 C3 H3A . . 120.1 ?
    C3 C4 C5 . . 120.63(14) ?
    C3 C4 H4A . . 119.7 ?
    C5 C4 H4A . . 119.7 ?
    C6 C5 C4 . . 119.82(14) ?
    C6 C5 H5A . . 120.1 ?
    C4 C5 H5A . . 120.1 ?
    C5 C6 C7 . . 119.76(13) ?
    C5 C6 C8 . . 121.34(13) ?
    C7 C6 C8 . . 118.86(13) ?
    C2 C7 C6 . . 120.11(13) ?
    C2 C7 H7A . . 119.9 ?
    C6 C7 H7A . . 119.9 ?
    C6 C8 C9 . . 112.34(11) ?
    C6 C8 H8A . . 109.1 ?
    C9 C8 H8A . . 109.1 ?
    C6 C8 H8B . . 109.1 ?
    C9 C8 H8B . . 109.1 ?
    H8A C8 H8B . . 107.9 ?
    C10 C9 C8 . . 113.03(11) ?
    C10 C9 H9A . . 109.0 ?
    C8 C9 H9A . . 109.0 ?
    C10 C9 H9B . . 109.0 ?
    C8 C9 H9B . . 109.0 ?
    H9A C9 H9B . . 107.8 ?
    N2 C10 N1 . . 111.34(11) ?
    N2 C10 C9 . . 125.71(12) ?
    N1 C10 C9 . . 122.95(11) ?
    O3 C11 N3 . . 129.95(12) ?
    O3 C11 N1 . . 126.41(12) ?
    N3 C11 N1 . . 103.64(11) ?
    C13 C12 C17 . . 120.63(12) ?
    C13 C12 N1 . . 120.78(13) ?
    C17 C12 N1 . . 118.57(12) ?
    C12 C13 C14 . . 119.61(16) ?
    C12 C13 H13A . . 120.2 ?
    C14 C13 H13A . . 120.2 ?
    C15 C14 C13 . . 119.77(17) ?
    C15 C14 H14A . . 120.1 ?
    C13 C14 H14A . . 120.1 ?
    C14 C15 C16 . . 121.40(15) ?
    C14 C15 H15A . . 119.3 ?
    C16 C15 H15A . . 119.3 ?
    C15 C16 C17 . . 119.44(15) ?
    C15 C16 H16A . . 120.3 ?
    C17 C16 H16A . . 120.3 ?
    O2 C17 C12 . . 115.80(11) ?
    O2 C17 C16 . . 125.05(13) ?
    C12 C17 C16 . . 119.14(13) ?
    O2 C18 H18A . . 109.5 ?
    O2 C18 H18B . . 109.5 ?
    H18A C18 H18B . . 109.5 ?
    O2 C18 H18C . . 109.5 ?
    H18A C18 H18C . . 109.5 ?
    H18B C18 H18C . . 109.5 ?
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
    O3 H3 N3 3_757 0.82 1.94 2.7569(15) 173
    C5 H5A O1 2_546 0.93 2.59 3.406(2) 147
    C8 H8A O2 . 0.97 2.57 3.485(2) 157
    C4 H4A Cg3 1_455 0.93 3.25 4.004(3) 140
    C7 H7A Cg3 1_555 0.93 3.16 4.067(3) 165
    C18 H18A Cg2 4_554 0.96 3.03 3.400(3) 105
    C18 H18B Cg2 4_554 0.96 3.08 3.400(3) 101
data_global
_journal_date_recd_electronic     2008-10-06
_journal_date_accepted     2008-10-17
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue     11
_journal_page_first     o2180
_journal_page_last     o2180
_journal_paper_category     QO
_journal_coeditor_code     HK2549
_publ_contact_author_name     ' Nasim Hasan Rama'
_publ_contact_author_address
;
DEPARTMENT OF CHEMISTRY,
QUAID-I-AZAM UNIVERSITY,
ISLAMABAD 45320,
PAKISTAN
;
_publ_contact_author_email     nasimhrama@yahoo.com
_publ_contact_author_fax     '92-51-2873869'
_publ_contact_author_phone     '92-51-2211034'
_publ_section_title
;
5-(3-Methoxyphenethyl)-4-(2-methoxyphenyl)-4H-1,2,4-triazol-3-ol
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Muhammad Hanif' .
;
Department of Chemistry,
Quaid-I-Azam University,
Islamabad 45320,
Pakistan
;
    'Ghulam Qadeer' .
;
Department of Chemistry,
Quaid-I-Azam University,
Islamabad 45320,
Pakistan
;
    'Nasim Hasan Rama' .
;
Department of Chemistry,
Quaid-I-Azam University,
Islamabad 45320,
Pakistan
;
    'Wai-Yeung Wong' .
;
Department of Chemistry
Hong Kong Baptist University
Waterloo Road
Kowloon Tong
Hong Kong
;
