#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/97/2219739.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_2219739
loop_
_publ_author_name
'Özel Güven, Özden'
'Tahtacı, Hakan'
'Coles, Simon J.'
'Hökelek, Tuncer'
_publ_section_title
;
 1-[2-(4-Bromobenzyloxy)-2-phenylethyl]-1H-1,2,4-triazole
;
_journal_coeditor_code           XU2450
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1914
_journal_page_last               o1915
_journal_paper_doi               10.1107/S1600536808027748
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C17 H16 Br N3 O'
_chemical_formula_moiety         'C17 H16 Br N3 O'
_chemical_formula_sum            'C17 H16 Br N3 O'
_chemical_formula_weight         358.24
_chemical_name_systematic
;
1-[2-(4-Bromobenzyloxy)-2-phenylethyl]-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                 100.3170(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.2070(2)
_cell_length_b                   13.7948(3)
_cell_length_c                   11.4007(2)
_cell_measurement_reflns_used    3224
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.910
_cell_volume                     1579.30(5)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material
'WinGX publication routines (Farrugia, 1999) and PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker--Nonius Kappa CCD diffractometer'
_diffrn_measurement_method       'φ & 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  0.0505
_diffrn_reflns_av_sigmaI/netI    0.0448
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18914
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.30
_exptl_absorpt_coefficient_mu    2.608
_exptl_absorpt_correction_T_max  0.590
_exptl_absorpt_correction_T_min  0.400
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.528
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3617
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0365
_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)+(0.0282P)²+1.0904P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0762
_refine_ls_wR_factor_ref         0.0822
_reflns_number_gt                2901
_reflns_number_total             3617
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2450.cif
_cod_data_source_block           I
_cod_original_cell_volume        1579.31(5)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2219739
_cod_database_fobs_code          2219739
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
Br Br 0.01308(3) 0.204749(18) 0.24099(2) 0.03377(10) Uani d . 1
O O 0.23831(15) 0.48903(11) 0.72395(13) 0.0219(3) Uani d . 1
N N1 0.43625(18) 0.62535(13) 0.70844(15) 0.0209(4) Uani d . 1
N N2 0.4116(2) 0.71851(14) 0.67091(18) 0.0262(4) Uani d . 1
N N3 0.4832(2) 0.62873(15) 0.52812(17) 0.0264(4) Uani d . 1
C C1 0.4421(2) 0.71587(17) 0.5630(2) 0.0260(5) Uani d . 1
H H1 0.4357 0.7703 0.5141 0.031 Uiso calc R 1
C C2 0.4777(2) 0.57391(17) 0.62277(19) 0.0250(5) Uani d . 1
H H2 0.4998 0.5085 0.6287 0.030 Uiso calc R 1
C C3 0.4052(2) 0.59254(17) 0.82170(18) 0.0230(5) Uani d . 1
H H3A 0.4249 0.6441 0.8800 0.028 Uiso calc R 1
H H3B 0.4615 0.5377 0.8500 0.028 Uiso calc R 1
C C4 0.2599(2) 0.56308(16) 0.81142(18) 0.0209(5) Uani d . 1
H H4 0.2028 0.6187 0.7839 0.025 Uiso calc R 1
C C5 0.2348(2) 0.53134(16) 0.93291(18) 0.0203(5) Uani d . 1
C C6 0.2718(2) 0.43995(17) 0.9773(2) 0.0264(5) Uani d . 1
H H6 0.3090 0.3959 0.9308 0.032 Uiso calc R 1
C C7 0.2536(2) 0.41385(19) 1.0911(2) 0.0292(5) Uani d . 1
H H7 0.2780 0.3523 1.1202 0.035 Uiso calc R 1
C C8 0.1994(3) 0.47886(19) 1.1609(2) 0.0306(6) Uani d . 1
H H8 0.1876 0.4614 1.2371 0.037 Uiso calc R 1
C C9 0.1627(3) 0.57037(19) 1.1170(2) 0.0323(6) Uani d . 1
H H9 0.1269 0.6147 1.1640 0.039 Uiso calc R 1
C C10 0.1791(2) 0.59612(18) 1.0031(2) 0.0263(5) Uani d . 1
H H10 0.1527 0.6572 0.9734 0.032 Uiso calc R 1
C C11 0.1027(2) 0.45894(17) 0.69514(19) 0.0220(5) Uani d . 1
H H11A 0.0452 0.5153 0.6806 0.026 Uiso calc R 1
H H11B 0.0788 0.4230 0.7613 0.026 Uiso calc R 1
C C12 0.0843(2) 0.39583(16) 0.58547(18) 0.0199(5) Uani d . 1
C C13 0.1877(2) 0.37627(17) 0.52494(19) 0.0224(5) Uani d . 1
H H13 0.2718 0.4021 0.5525 0.027 Uiso calc R 1
C C14 0.1669(2) 0.31831(17) 0.42329(19) 0.0240(5) Uani d . 1
H H14 0.2367 0.3050 0.3833 0.029 Uiso calc R 1
C C15 0.0416(2) 0.28084(16) 0.38240(19) 0.0242(5) Uani d . 1
C C16 -0.0634(2) 0.30004(17) 0.4409(2) 0.0247(5) Uani d . 1
H H16 -0.1475 0.2748 0.4125 0.030 Uiso calc R 1
C C17 -0.0413(2) 0.35727(17) 0.54222(19) 0.0225(5) Uani d . 1
H H17 -0.1114 0.3702 0.5820 0.027 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 0.0030 0.0020 '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'
Br Br -0.2900 2.4600 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 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
C4 O C11 113.20(16)
C2 N1 N2 109.63(18)
C2 N1 C3 129.13(19)
N2 N1 C3 120.95(18)
C1 N2 N1 101.85(19)
C2 N3 C1 101.93(19)
N2 C1 N3 115.7(2)
N2 C1 H1 122.2
N3 C1 H1 122.2
N3 C2 N1 110.9(2)
N3 C2 H2 124.5
N1 C2 H2 124.5
N1 C3 C4 112.24(18)
N1 C3 H3A 109.2
C4 C3 H3A 109.2
N1 C3 H3B 109.2
C4 C3 H3B 109.2
H3A C3 H3B 107.9
O C4 C5 113.84(18)
O C4 C3 105.84(17)
C5 C4 C3 109.14(18)
O C4 H4 109.3
C5 C4 H4 109.3
C3 C4 H4 109.3
C6 C5 C10 119.3(2)
C6 C5 C4 121.1(2)
C10 C5 C4 119.6(2)
C5 C6 C7 120.2(2)
C5 C6 H6 119.9
C7 C6 H6 119.9
C8 C7 C6 120.3(2)
C8 C7 H7 119.8
C6 C7 H7 119.8
C7 C8 C9 119.6(2)
C7 C8 H8 120.2
C9 C8 H8 120.2
C8 C9 C10 120.2(2)
C8 C9 H9 119.9
C10 C9 H9 119.9
C9 C10 C5 120.4(2)
C9 C10 H10 119.8
C5 C10 H10 119.8
O C11 C12 109.32(18)
O C11 H11A 109.8
C12 C11 H11A 109.8
O C11 H11B 109.8
C12 C11 H11B 109.8
H11A C11 H11B 108.3
C13 C12 C17 118.9(2)
C13 C12 C11 122.1(2)
C17 C12 C11 118.9(2)
C12 C13 C14 120.6(2)
C12 C13 H13 119.7
C14 C13 H13 119.7
C15 C14 C13 119.3(2)
C15 C14 H14 120.3
C13 C14 H14 120.3
C14 C15 C16 121.0(2)
C14 C15 Br 118.98(18)
C16 C15 Br 119.97(18)
C17 C16 C15 119.1(2)
C17 C16 H16 120.4
C15 C16 H16 120.4
C16 C17 C12 121.0(2)
C16 C17 H17 119.5
C12 C17 H17 119.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br C15 1.902(2)
O C4 1.417(3)
O C11 1.426(3)
N1 C2 1.336(3)
N1 N2 1.363(3)
N1 C3 1.456(3)
N2 C1 1.323(3)
N3 C2 1.327(3)
C12 C13 1.387(3)
C12 C11 1.507(3)
C13 C14 1.393(3)
C13 H13 0.9300
C14 H14 0.9300
C15 C14 1.381(3)
C15 C16 1.385(3)
C16 C17 1.384(3)
C16 H16 0.9300
C17 C12 1.394(3)
C17 H17 0.9300
C1 N3 1.356(3)
C1 H1 0.9300
C2 H2 0.9300
C3 C4 1.523(3)
C3 H3A 0.9700
C3 H3B 0.9700
C4 C5 1.517(3)
C4 H4 0.9800
C5 C10 1.387(3)
C6 C5 1.386(3)
C6 C7 1.390(3)
C6 H6 0.9300
C7 H7 0.9300
C8 C7 1.379(4)
C8 C9 1.385(4)
C8 H8 0.9300
C9 H9 0.9300
C10 C9 1.385(3)
C10 H10 0.9300
C11 H11A 0.9700
C11 H11B 0.9700
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
C13 H13 O . 0.93 2.37 2.723(3) 102.00 yes
C11 H11A Cg3 3_655 0.97 2.84 3.687(2) 146.63 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
C11 O C4 C5 65.5(2)
C11 O C4 C3 -174.60(17)
C4 O C11 C12 168.62(17)
C2 N1 N2 C1 -0.5(2)
C3 N1 N2 C1 -174.8(2)
N2 N1 C2 N3 0.4(3)
C3 N1 C2 N3 174.1(2)
N2 N1 C3 C4 83.5(2)
C2 N1 C3 C4 -89.6(3)
N1 N2 C1 N3 0.4(3)
C1 N3 C2 N1 -0.1(3)
N2 C1 N3 C2 -0.2(3)
N1 C3 C4 O 58.0(2)
N1 C3 C4 C5 -179.15(18)
O C4 C5 C6 38.9(3)
O C4 C5 C10 -143.9(2)
C3 C4 C5 C6 -79.1(3)
C3 C4 C5 C10 98.1(2)
C6 C5 C10 C9 1.1(4)
C4 C5 C10 C9 -176.2(2)
C7 C6 C5 C10 -0.2(3)
C7 C6 C5 C4 177.1(2)
C5 C6 C7 C8 -0.5(4)
C9 C8 C7 C6 0.3(4)
C7 C8 C9 C10 0.6(4)
C5 C10 C9 C8 -1.3(4)
C13 C12 C11 O -1.9(3)
C17 C12 C11 O 179.24(19)
C11 C12 C13 C14 -179.4(2)
C17 C12 C13 C14 -0.6(3)
C12 C13 C14 C15 0.5(3)
Br C15 C14 C13 178.28(17)
C16 C15 C14 C13 0.0(3)
Br C15 C16 C17 -178.62(17)
C14 C15 C16 C17 -0.4(3)
C15 C16 C17 C12 0.2(3)
C16 C17 C12 C11 179.1(2)
C16 C17 C12 C13 0.3(3)
