#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/98/2219886.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_2219886
loop_
_publ_author_name
'Hanif, Muhammad'
'Qadeer, Ghulam'
'Rama, Nasim Hasan'
'Wong, Wai-Yeung'
_publ_section_title
;
 5-(3-Methoxyphenethyl)-4-(2-methoxyphenyl)-4H-1,2,4-triazol-3-ol
;
_journal_coeditor_code           HK2549
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2180
_journal_paper_doi               10.1107/S1600536808033990
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C18 H19 N3 O3'
_chemical_formula_moiety         'C18 H19 N3 O3'
_chemical_formula_sum            'C18 H19 N3 O3'
_chemical_formula_weight         325.36
_chemical_melting_point          454.0(10)
_chemical_name_systematic
;
5-(3-Methoxyphenethyl)-4-(2-methoxyphenyl)-4H-1,2,4-triazol-3-ol
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 98.192(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5030(11)
_cell_length_b                   14.1172(14)
_cell_length_c                   11.3226(11)
_cell_measurement_reflns_used    9949
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.43
_cell_volume                     1661.7(3)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'φ and ω'
_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  0.0184
_diffrn_reflns_av_sigmaI/netI    0.0216
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9949
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.43
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9016
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.559
_refine_diff_density_min         -0.399
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         4026
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0478
_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)+(0.0854P)²+0.2782P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1339
_refine_ls_wR_factor_ref         0.1455
_reflns_number_gt                3212
_reflns_number_total             4026
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2549.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2219886
_cod_database_fobs_code          2219886
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'
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
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
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
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_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
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_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
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24740999
