#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/48/2224815.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_2224815
loop_
_publ_author_name
'Özel Güven, Özden'
'Tahtacı, Hakan'
'Coles, Simon J.'
'Hökelek, Tuncer'
_publ_section_title
;
 1-[2-(2,6-Dichlorobenzyloxy)-2-(2-furyl)ethyl]-1H-1,2,4-triazole
;
_journal_coeditor_code           XU2704
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o107
_journal_page_last               o108
_journal_paper_doi               10.1107/S1600536809052568
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H13 Cl2 N3 O2'
_chemical_formula_moiety         'C15 H13 Cl2 N3 O2'
_chemical_formula_sum            'C15 H13 Cl2 N3 O2'
_chemical_formula_weight         338.18
_chemical_name_systematic
;
1-[2-(2,6-Dichlorobenzyloxy)-2-(2-furyl)ethyl]-1H-1,2,4-triazole
;
_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                 114.4550(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5853(3)
_cell_length_b                   12.4960(2)
_cell_length_c                   12.5850(3)
_cell_measurement_reflns_used    23020
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1515.32(6)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998)'
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material
'WinGX (Farrugia, 1999) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker--Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'φ and ω 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  0.0579
_diffrn_reflns_av_sigmaI/netI    0.0314
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            33067
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.26
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.438
_exptl_absorpt_correction_T_max  0.955
_exptl_absorpt_correction_T_min  0.837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.203
_refine_diff_density_min         -0.757
_refine_ls_extinction_coef       0.051(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3438
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0674
_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)+(0.0984P)²+1.9705P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1678
_refine_ls_wR_factor_ref         0.1795
_reflns_number_gt                2775
_reflns_number_total             3438
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2704.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2224815
_cod_database_fobs_code          2224815
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.32066(8) 0.66344(7) 1.08482(8) 0.0470(3) Uani d . 1 . .
Cl Cl2 0.29005(8) 0.31220(7) 0.82358(9) 0.0497(3) Uani d . 1 . .
O O1 0.07950(17) 0.54757(14) 0.86960(15) 0.0231(4) Uani d . 1 . .
O O2 -0.1088(3) 0.5914(2) 0.5685(2) 0.0483(6) Uani d . 1 . .
N N1 -0.0576(2) 0.71549(17) 0.93071(19) 0.0226(5) Uani d . 1 . .
N N2 -0.0121(2) 0.81516(18) 0.9183(2) 0.0284(5) Uani d . 1 . .
N N3 0.0458(2) 0.7770(2) 1.1089(2) 0.0298(5) Uani d . 1 . .
C C1 0.0483(3) 0.8475(2) 1.0282(3) 0.0300(6) Uani d . 1 . .
H H1 0.0898 0.9144 1.0487 0.036 Uiso calc R 1 . .
C C2 -0.0207(3) 0.6947(2) 1.0435(2) 0.0255(5) Uani d . 1 . .
H H2 -0.0393 0.6309 1.0724 0.031 Uiso calc R 1 . .
C C3 -0.1260(3) 0.6463(2) 0.8301(2) 0.0248(5) Uani d . 1 . .
H H3A -0.2023 0.6846 0.7706 0.030 Uiso calc R 1 . .
H H3B -0.1638 0.5842 0.8530 0.030 Uiso calc R 1 . .
C C4 -0.0241(2) 0.6098(2) 0.7800(2) 0.0228(5) Uani d . 1 . .
H H4 0.0197 0.6727 0.7628 0.027 Uiso calc R 1 . .
C C5 -0.0952(3) 0.5454(2) 0.6705(2) 0.0250(5) Uani d . 1 . .
C C6 -0.1805(4) 0.5198(4) 0.4817(3) 0.0582(11) Uani d . 1 . .
H H6 -0.2048 0.5311 0.4026 0.070 Uiso calc R 1 . .
C C7 -0.2101(3) 0.4328(3) 0.5259(3) 0.0457(9) Uani d . 1 . .
H H7 -0.2564 0.3726 0.4847 0.055 Uiso calc R 1 . .
C C8 -0.1574(3) 0.4484(3) 0.6500(3) 0.0429(8) Uani d . 1 . .
H H8 -0.1646 0.4016 0.7047 0.051 Uiso calc R 1 . .
C C9 0.2081(3) 0.5444(2) 0.8579(2) 0.0244(5) Uani d . 1 . .
H H9A 0.2416 0.6164 0.8565 0.029 Uiso calc R 1 . .
H H9B 0.1961 0.5086 0.7859 0.029 Uiso calc R 1 . .
C C10 0.3091(2) 0.4839(2) 0.9611(2) 0.0224(5) Uani d . 1 . .
C C11 0.3640(3) 0.5315(2) 1.0718(2) 0.0283(6) Uani d . 1 . .
C C12 0.4517(3) 0.4781(3) 1.1713(3) 0.0424(8) Uani d . 1 . .
H H12 0.4849 0.5122 1.2435 0.051 Uiso calc R 1 . .
C C13 0.4890(3) 0.3753(3) 1.1629(3) 0.0459(9) Uani d . 1 . .
H H13 0.5469 0.3388 1.2297 0.055 Uiso calc R 1 . .
C C14 0.4416(3) 0.3250(2) 1.0558(4) 0.0427(9) Uani d . 1 . .
H H14 0.4695 0.2555 1.0500 0.051 Uiso calc R 1 . .
C C15 0.3507(3) 0.3794(2) 0.9559(3) 0.0304(6) Uani d . 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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C9 O1 C4 . . 112.62(18) ?
C5 O2 C6 . . 106.5(3) ?
N2 N1 C3 . . 120.9(2) ?
C2 N1 N2 . . 109.7(2) ?
C2 N1 C3 . . 129.2(2) ?
C1 N2 N1 . . 101.5(2) ?
C2 N3 C1 . . 102.1(2) ?
N2 C1 N3 . . 115.7(2) ?
N2 C1 H1 . . 122.1 ?
N3 C1 H1 . . 122.1 ?
N1 C2 H2 . . 124.5 ?
N3 C2 N1 . . 110.9(2) ?
N3 C2 H2 . . 124.5 ?
N1 C3 C4 . . 110.8(2) ?
N1 C3 H3A . . 109.5 ?
N1 C3 H3B . . 109.5 ?
C4 C3 H3A . . 109.5 ?
C4 C3 H3B . . 109.5 ?
H3A C3 H3B . . 108.1 ?
O1 C4 C3 . . 106.1(2) ?
O1 C4 C5 . . 111.1(2) ?
O1 C4 H4 . . 109.3 ?
C3 C4 H4 . . 109.3 ?
C5 C4 C3 . . 111.5(2) ?
C5 C4 H4 . . 109.3 ?
O2 C5 C4 . . 117.2(2) ?
C8 C5 O2 . . 110.3(3) ?
C8 C5 C4 . . 132.5(3) ?
O2 C6 H6 . . 124.7 ?
C7 C6 O2 . . 110.6(3) ?
C7 C6 H6 . . 124.7 ?
C6 C7 C8 . . 107.1(3) ?
C6 C7 H7 . . 126.5 ?
C8 C7 H7 . . 126.5 ?
C5 C8 C7 . . 105.6(3) ?
C5 C8 H8 . . 127.2 ?
C7 C8 H8 . . 127.2 ?
O1 C9 C10 . . 107.01(19) ?
O1 C9 H9A . . 110.3 ?
O1 C9 H9B . . 110.3 ?
C10 C9 H9A . . 110.3 ?
C10 C9 H9B . . 110.3 ?
H9A C9 H9B . . 108.6 ?
C11 C10 C9 . . 120.1(2) ?
C15 C10 C9 . . 124.0(2) ?
C15 C10 C11 . . 115.9(2) ?
C10 C11 Cl1 . . 118.7(2) ?
C12 C11 C10 . . 122.9(3) ?
C12 C11 Cl1 . . 118.5(3) ?
C11 C12 H12 . . 120.3 ?
C13 C12 C11 . . 119.5(3) ?
C13 C12 H12 . . 120.3 ?
C12 C13 C14 . . 120.5(3) ?
C12 C13 H13 . . 119.8 ?
C14 C13 H13 . . 119.8 ?
C13 C14 C15 . . 119.5(3) ?
C13 C14 H14 . . 120.3 ?
C15 C14 H14 . . 120.3 ?
C10 C15 Cl2 . . 120.2(2) ?
C10 C15 C14 . . 121.8(3) ?
C14 C15 Cl2 . . 118.1(2) ?
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
N1 N2 . 1.367(3) ?
C1 N2 . 1.324(4) ?
C1 N3 . 1.352(4) ?
C1 H1 . 0.9300 ?
C2 N3 . 1.323(4) ?
C2 N1 . 1.333(3) ?
C2 H2 . 0.9300 ?
C3 N1 . 1.455(3) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 O1 . 1.434(3) ?
C4 C3 . 1.527(4) ?
C4 C5 . 1.501(4) ?
C4 H4 . 0.9800 ?
C5 O2 . 1.359(4) ?
C5 C8 . 1.352(4) ?
C6 O2 . 1.373(4) ?
C6 C7 . 1.317(6) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.438(5) ?
C7 H7 . 0.9300 ?
C8 H8 . 0.9300 ?
C9 O1 . 1.429(3) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C10 C9 . 1.501(3) ?
C10 C11 . 1.401(4) ?
C10 C15 . 1.389(4) ?
C11 Cl1 . 1.737(3) ?
C11 C12 . 1.383(4) ?
C12 C13 . 1.361(6) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.380(6) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.403(4) ?
C14 H14 . 0.9300 ?
C15 Cl2 . 1.733(3) ?
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
_geom_hbond_publ_flag
C2 H2 O1 3_567 0.93 2.44 3.363(3) 173 yes
C9 H9B Cl2 . 0.97 2.62 3.109(3) 112 yes
C1 H1 Cg2 4_454 0.93 2.79 3.488(4) 133 yes
C7 H7 Cg1 2_646 0.93 2.93 3.570(4) 127 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 N1 N2 C1 . . . . -1.0(3) ?
C3 N1 N2 C1 . . . . -176.9(2) ?
N3 C1 N2 N1 . . . . 0.4(3) ?
N2 C1 N3 C2 . . . . 0.3(3) ?
N3 C2 N1 N2 . . . . 1.3(3) ?
N3 C2 N1 C3 . . . . 176.7(2) ?
N1 C2 N3 C1 . . . . -1.0(3) ?
C4 C3 N1 C2 . . . . -107.0(3) ?
C4 C3 N1 N2 . . . . 68.0(3) ?
C3 C4 O1 C9 . . . . -156.0(2) ?
C5 C4 O1 C9 . . . . 82.6(3) ?
O1 C4 C3 N1 . . . . 63.3(3) ?
C5 C4 C3 N1 . . . . -175.5(2) ?
O1 C4 C5 O2 . . . . -132.0(2) ?
O1 C4 C5 C8 . . . . 51.7(4) ?
C3 C4 C5 O2 . . . . 109.7(3) ?
C3 C4 C5 C8 . . . . -66.6(4) ?
C4 C5 O2 C6 . . . . -177.9(3) ?
C8 C5 O2 C6 . . . . -0.8(4) ?
O2 C5 C8 C7 . . . . 1.5(4) ?
C4 C5 C8 C7 . . . . 178.0(3) ?
C7 C6 O2 C5 . . . . -0.4(4) ?
O2 C6 C7 C8 . . . . 1.3(4) ?
C6 C7 C8 C5 . . . . -1.7(4) ?
C10 C9 O1 C4 . . . . 176.0(2) ?
C11 C10 C9 O1 . . . . -73.1(3) ?
C15 C10 C9 O1 . . . . 104.8(3) ?
C9 C10 C11 Cl1 . . . . -3.8(3) ?
C9 C10 C11 C12 . . . . 176.5(2) ?
C15 C10 C11 Cl1 . . . . 178.21(19) ?
C15 C10 C11 C12 . . . . -1.5(4) ?
C9 C10 C15 Cl2 . . . . 2.2(3) ?
C9 C10 C15 C14 . . . . -177.5(2) ?
C11 C10 C15 Cl2 . . . . -179.85(19) ?
C11 C10 C15 C14 . . . . 0.4(4) ?
C10 C11 C12 C13 . . . . 0.9(4) ?
Cl1 C11 C12 C13 . . . . -178.8(2) ?
C11 C12 C13 C14 . . . . 0.9(4) ?
C12 C13 C14 C15 . . . . -2.0(4) ?
C13 C14 C15 Cl2 . . . . -178.4(2) ?
C13 C14 C15 C10 . . . . 1.3(4) ?
