#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/55/2225591.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_2225591
loop_
_publ_author_name
'Özel Güven, Özden'
'Bayraktar, Meral'
'Coles, Simon J.'
'Hökelek, Tuncer'
_publ_section_title
;
 2-(1H-Benzotriazol-1-yl)-1-phenylethanol
;
_journal_coeditor_code           IM2186
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o959
_journal_paper_doi               10.1107/S1600536810011098
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C14 H13 N3 O'
_chemical_formula_moiety         'C14 H13 N3 O'
_chemical_formula_sum            'C14 H13 N3 O'
_chemical_formula_weight         239.27
_chemical_name_systematic
;
2-(1H-Benzotriazol-1-yl)-1-phenylethanol
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.0731(3)
_cell_length_b                   8.6571(2)
_cell_length_c                   25.3436(7)
_cell_measurement_reflns_used    13033
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     2429.46(11)
_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)'
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Nonius Kappa CCD 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  0.0434
_diffrn_reflns_av_sigmaI/netI    0.0360
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            11997
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.09
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.233
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         2772
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0446
_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)+(0.0259P)²+1.6489P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1047
_reflns_number_gt                2447
_reflns_number_total             2772
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            im2186.cif
_cod_data_source_block           I
_cod_original_cell_volume        2429.50(10)
_cod_database_code               2225591
_cod_database_fobs_code          2225591
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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 0.02061(10) 0.04949(12) 0.40376(4) 0.0279(2) Uani d . 1 . .
H H1 0.090(2) 0.038(2) 0.4178(9) 0.054(6) Uiso d . 1 . .
N N1 0.25101(12) 0.48299(16) 0.44171(5) 0.0300(3) Uani d . 1 . .
N N2 0.18457(11) 0.44939(15) 0.40068(5) 0.0295(3) Uani d . 1 . .
N N3 0.08582(11) 0.37136(13) 0.41711(4) 0.0222(3) Uani d . 1 . .
C C1 0.19546(12) 0.42532(16) 0.48602(5) 0.0224(3) Uani d . 1 . .
C C2 0.22997(13) 0.43162(17) 0.53950(5) 0.0240(3) Uani d . 1 . .
H H2 0.3052(16) 0.479(2) 0.5494(7) 0.029(4) Uiso d . 1 . .
C C3 0.15335(14) 0.36306(17) 0.57508(5) 0.0253(3) Uani d . 1 . .
H H3 0.1736(15) 0.3631(19) 0.6119(7) 0.030(4) Uiso d . 1 . .
C C4 0.04479(14) 0.29030(16) 0.55904(6) 0.0255(3) Uani d . 1 . .
H H4 -0.0089(16) 0.240(2) 0.5866(8) 0.036(5) Uiso d . 1 . .
C C5 0.01041(13) 0.28261(16) 0.50680(6) 0.0228(3) Uani d . 1 . .
H H5 -0.0631(15) 0.232(2) 0.4957(7) 0.028(4) Uiso d . 1 . .
C C6 0.08867(12) 0.35214(15) 0.47059(5) 0.0199(3) Uani d . 1 . .
C C7 0.00031(13) 0.31427(16) 0.37785(5) 0.0229(3) Uani d . 1 . .
H H71 -0.0807(15) 0.3138(18) 0.3945(6) 0.022(4) Uiso d . 1 . .
H H72 0.0019(15) 0.388(2) 0.3473(7) 0.028(4) Uiso d . 1 . .
C C8 0.03379(12) 0.15050(16) 0.36022(5) 0.0216(3) Uani d . 1 . .
H H8 0.1203(14) 0.1535(17) 0.3473(6) 0.021(4) Uiso d . 1 . .
C C9 -0.04730(12) 0.09913(16) 0.31533(5) 0.0214(3) Uani d . 1 . .
C C10 -0.13758(13) -0.00987(17) 0.32359(5) 0.0248(3) Uani d . 1 . .
H H10 -0.1479(15) -0.0567(19) 0.3588(7) 0.032(4) Uiso d . 1 . .
C C11 -0.21348(14) -0.05425(19) 0.28253(6) 0.0303(3) Uani d . 1 . .
H H11 -0.2784(17) -0.134(2) 0.2882(7) 0.039(5) Uiso d . 1 . .
C C12 -0.19924(15) 0.00902(19) 0.23260(6) 0.0317(3) Uani d . 1 . .
H H12 -0.2518(18) -0.023(2) 0.2038(8) 0.043(5) Uiso d . 1 . .
C C13 -0.10914(15) 0.11692(19) 0.22396(6) 0.0318(3) Uani d . 1 . .
H H13 -0.0995(17) 0.162(2) 0.1892(8) 0.041(5) Uiso d . 1 . .
C C14 -0.03327(14) 0.16238(17) 0.26496(6) 0.0270(3) Uani d . 1 . .
H H14 0.0301(16) 0.238(2) 0.2584(7) 0.032(4) Uiso 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'
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
C8 O1 H1 . . 107.8(15) ?
N2 N1 C1 . . 108.51(12) ?
N1 N2 N3 . . 108.76(11) ?
N2 N3 C6 . . 110.37(11) ?
N2 N3 C7 . . 118.95(11) ?
C6 N3 C7 . . 130.55(12) ?
N1 C1 C2 . . 130.58(13) ?
N1 C1 C6 . . 108.35(12) ?
C6 C1 C2 . . 121.07(13) ?
C1 C2 H2 . . 120.1(10) ?
C3 C2 C1 . . 116.58(13) ?
C3 C2 H2 . . 123.2(10) ?
C2 C3 C4 . . 121.87(13) ?
C2 C3 H3 . . 119.6(10) ?
C4 C3 H3 . . 118.5(10) ?
C3 C4 H4 . . 119.4(11) ?
C5 C4 C3 . . 122.08(13) ?
C5 C4 H4 . . 118.5(11) ?
C4 C5 C6 . . 115.99(13) ?
C4 C5 H5 . . 122.4(10) ?
C6 C5 H5 . . 121.6(10) ?
N3 C6 C1 . . 104.01(12) ?
N3 C6 C5 . . 133.57(13) ?
C1 C6 C5 . . 122.41(12) ?
N3 C7 C8 . . 110.81(11) ?
N3 C7 H71 . . 107.3(9) ?
N3 C7 H72 . . 107.4(10) ?
C8 C7 H71 . . 109.9(9) ?
C8 C7 H72 . . 111.1(10) ?
H71 C7 H72 . . 110.3(13) ?
O1 C8 C7 . . 108.63(11) ?
O1 C8 C9 . . 110.04(11) ?
O1 C8 H8 . . 111.5(9) ?
C9 C8 C7 . . 110.30(11) ?
C9 C8 H8 . . 108.9(9) ?
C7 C8 H8 . . 107.4(9) ?
C10 C9 C8 . . 120.79(12) ?
C10 C9 C14 . . 118.89(13) ?
C14 C9 C8 . . 120.31(13) ?
C9 C10 C11 . . 120.60(14) ?
C9 C10 H10 . . 119.9(10) ?
C11 C10 H10 . . 119.5(10) ?
C10 C11 H11 . . 120.9(11) ?
C12 C11 C10 . . 120.28(15) ?
C12 C11 H11 . . 118.8(10) ?
C11 C12 H12 . . 120.1(12) ?
C13 C12 C11 . . 119.50(14) ?
C13 C12 H12 . . 120.4(12) ?
C12 C13 C14 . . 120.49(14) ?
C12 C13 H13 . . 119.5(11) ?
C14 C13 H13 . . 120.0(12) ?
C9 C14 H14 . . 120.0(11) ?
C13 C14 C9 . . 120.24(14) ?
C13 C14 H14 . . 119.8(11) ?
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
O1 C8 . 1.4154(17) ?
O1 H1 . 0.86(2) ?
N1 C1 . 1.3743(18) ?
N2 N1 . 1.3067(17) ?
N3 N2 . 1.3511(16) ?
N3 C6 . 1.3659(16) ?
N3 C7 . 1.4597(17) ?
C1 C2 . 1.4091(18) ?
C2 H2 . 0.962(18) ?
C3 C2 . 1.373(2) ?
C3 H3 . 0.960(17) ?
C4 C3 . 1.417(2) ?
C4 C5 . 1.3793(19) ?
C4 H4 . 1.014(19) ?
C5 H5 . 0.965(17) ?
C6 C1 . 1.3974(19) ?
C6 C5 . 1.3983(19) ?
C7 H71 . 0.992(17) ?
C7 H72 . 1.003(17) ?
C8 C7 . 1.5320(19) ?
C8 C9 . 1.5161(18) ?
C8 H8 . 1.012(16) ?
C9 C10 . 1.390(2) ?
C9 C14 . 1.3978(19) ?
C10 C11 . 1.392(2) ?
C10 H10 . 0.986(18) ?
C11 H11 . 1.005(19) ?
C12 C13 . 1.384(2) ?
C12 C11 . 1.388(2) ?
C12 H12 . 0.98(2) ?
C13 H13 . 0.97(2) ?
C14 C13 . 1.393(2) ?
C14 H14 . 0.972(18) ?
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
O1 H1 N1 9_545 0.85(2) 1.92(2) 2.766(2) 170(2) yes
C11 H11 Cg3 7_545 1.01(2) 2.94(2) 3.850(2) 151.0(10) 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
N2 N1 C1 C2 . . . . -179.62(15) ?
N2 N1 C1 C6 . . . . 0.05(17) ?
N3 N2 N1 C1 . . . . 0.35(17) ?
C6 N3 N2 N1 . . . . -0.64(16) ?
C7 N3 N2 N1 . . . . -177.00(12) ?
N2 N3 C6 C1 . . . . 0.64(15) ?
N2 N3 C6 C5 . . . . 179.36(15) ?
N2 N3 C7 C8 . . . . 90.35(15) ?
C6 N3 C7 C8 . . . . -85.16(17) ?
C7 N3 C6 C1 . . . . 176.45(13) ?
C7 N3 C6 C5 . . . . -4.8(3) ?
N1 C1 C2 C3 . . . . 179.42(15) ?
C6 C1 C2 C3 . . . . -0.2(2) ?
C4 C3 C2 C1 . . . . -0.3(2) ?
C5 C4 C3 C2 . . . . 0.7(2) ?
C3 C4 C5 C6 . . . . -0.5(2) ?
N3 C6 C1 N1 . . . . -0.42(15) ?
N3 C6 C1 C2 . . . . 179.29(13) ?
C5 C6 C1 N1 . . . . -179.32(13) ?
C5 C6 C1 C2 . . . . 0.4(2) ?
N3 C6 C5 C4 . . . . -178.54(14) ?
C1 C6 C5 C4 . . . . 0.0(2) ?
O1 C8 C7 N3 . . . . 65.40(14) ?
C9 C8 C7 N3 . . . . -173.92(11) ?
O1 C8 C9 C10 . . . . 13.06(17) ?
O1 C8 C9 C14 . . . . -167.73(12) ?
C7 C8 C9 C10 . . . . -106.78(15) ?
C7 C8 C9 C14 . . . . 72.44(16) ?
C8 C9 C10 C11 . . . . 178.62(13) ?
C14 C9 C10 C11 . . . . -0.6(2) ?
C8 C9 C14 C13 . . . . -178.95(13) ?
C10 C9 C14 C13 . . . . 0.3(2) ?
C9 C10 C11 C12 . . . . 0.5(2) ?
C13 C12 C11 C10 . . . . -0.2(2) ?
C11 C12 C13 C14 . . . . -0.2(2) ?
C9 C14 C13 C12 . . . . 0.1(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2621123
