#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/86/2218695.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_2218695
loop_
_publ_author_name
'Özel Güven, Özden'
'Tahtacı, Hakan'
'Coles, Simon J.'
'Hökelek, Tuncer'
_publ_section_title
;
 1-Phenyl-2-(1H-1,2,4-triazol-1-yl)ethanol
;
_journal_coeditor_code           FL2201
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1254
_journal_paper_doi               10.1107/S1600536808017303
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C10 H11 N3 O'
_chemical_formula_moiety         'C10 H11 N3 O'
_chemical_formula_sum            'C10 H11 N3 O'
_chemical_formula_weight         189.22
_chemical_name_systematic
;
1-Phenyl-2-(1H-1,2,4-triazol-1-yl)ethanol
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 108.5810(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.5356(2)
_cell_length_b                   10.1173(2)
_cell_length_c                   8.7127(2)
_cell_measurement_reflns_used    12727
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     963.85(3)
_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 (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXL97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type
'Bruker--Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13352
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.18
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.210
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         2208
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0419
_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)+(0.0583P)²+0.1287P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1028
_refine_ls_wR_factor_ref         0.1148
_reflns_number_gt                1647
_reflns_number_total             2208
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fl2201.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2218695
_cod_database_fobs_code          2218695
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_occupancy
O O 0.87872(10) 0.13609(12) 0.06628(11) 0.0588(3) Uani d 1
H H 0.813(2) 0.182(2) 0.013(3) 0.096(7) Uiso d 1
N N1 0.72669(9) 0.10513(11) 0.27992(13) 0.0434(3) Uani d 1
N N2 0.68815(10) 0.20410(13) 0.35760(14) 0.0521(3) Uani d 1
N N3 0.52850(11) 0.11273(16) 0.16751(19) 0.0727(4) Uani d 1
C C1 0.56896(13) 0.20320(19) 0.2849(2) 0.0630(4) Uani d 1
H H1 0.5169(17) 0.2639(19) 0.316(2) 0.081(6) Uiso d 1
C C2 0.63083(13) 0.05341(18) 0.1683(2) 0.0596(4) Uani d 1
H H2 0.6363(16) -0.0179(19) 0.098(2) 0.074(5) Uiso d 1
C C3 0.85650(11) 0.07494(15) 0.32125(17) 0.0445(3) Uani d 1
H H31 0.8629(14) -0.0199(17) 0.288(2) 0.063(5) Uiso d 1
H H32 0.8938(14) 0.0825(15) 0.439(2) 0.059(4) Uiso d 1
C C4 0.91941(11) 0.16584(13) 0.23363(14) 0.0376(3) Uani d 1
H H4 0.8978(11) 0.2558(13) 0.2499(15) 0.034(3) Uiso d 1
C C5 1.05661(10) 0.14872(12) 0.30176(14) 0.0354(3) Uani d 1
C C6 1.12425(12) 0.22987(15) 0.42648(16) 0.0480(3) Uani d 1
H H6 1.0823(15) 0.2996(17) 0.467(2) 0.070(5) Uiso d 1
C C7 1.24947(13) 0.21333(16) 0.49370(19) 0.0572(4) Uani d 1
H H7 1.2961(16) 0.2732(19) 0.584(2) 0.079(5) Uiso d 1
C C8 1.30805(13) 0.11523(17) 0.4370(2) 0.0566(4) Uani d 1
H H8 1.3973(17) 0.1018(18) 0.484(2) 0.078(5) Uiso d 1
C C9 1.24185(13) 0.03446(15) 0.31286(19) 0.0529(4) Uani d 1
H H9 1.2826(15) -0.0328(17) 0.269(2) 0.065(5) Uiso d 1
C C10 1.11643(12) 0.05072(13) 0.24487(16) 0.0426(3) Uani d 1
H H10 1.0711(14) -0.0032(15) 0.1553(19) 0.055(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
C4 O H 112.0(14)
C2 N1 N2 109.10(12)
C2 N1 C3 130.55(13)
N2 N1 C3 120.31(11)
C1 N2 N1 102.24(12)
C2 N3 C1 102.29(13)
N2 C1 N3 115.33(15)
N2 C1 H1 120.7(11)
N3 C1 H1 123.9(11)
N1 C2 H2 123.7(11)
N3 C2 N1 111.04(15)
N3 C2 H2 125.2(11)
N1 C3 C4 111.53(10)
N1 C3 H31 107.0(9)
N1 C3 H32 108.5(9)
C4 C3 H31 109.9(9)
C4 C3 H32 110.9(9)
H31 C3 H32 109.0(13)
O C4 C3 109.53(11)
O C4 C5 110.01(10)
O C4 H4 109.6(7)
C3 C4 H4 108.0(7)
C5 C4 C3 109.94(10)
C5 C4 H4 109.7(7)
C6 C5 C4 119.78(11)
C10 C5 C4 121.28(11)
C10 C5 C6 118.92(12)
C5 C6 H6 119.2(10)
C7 C6 C5 120.68(13)
C7 C6 H6 120.1(10)
C6 C7 H7 119.0(10)
C8 C7 C6 120.00(14)
C8 C7 H7 121.0(10)
C7 C8 H8 120.9(11)
C9 C8 C7 119.79(13)
C9 C8 H8 119.3(11)
C8 C9 C10 120.47(14)
C8 C9 H9 120.6(9)
C10 C9 H9 118.9(9)
C5 C10 C9 120.14(13)
C5 C10 H10 119.5(9)
C9 C10 H10 120.3(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O C4 1.4144(15)
O H 0.88(2)
N1 N2 1.3602(16)
N1 C2 1.3257(18)
N1 C3 1.4565(16)
N2 C1 1.3178(18)
N3 C2 1.322(2)
C1 N3 1.341(2)
C1 H1 0.96(2)
C2 H2 0.961(19)
C3 H31 1.012(17)
C3 H32 0.977(17)
C4 C3 1.5194(18)
C4 H4 0.966(13)
C5 C4 1.5128(16)
C5 C6 1.3869(18)
C5 C10 1.3866(18)
C6 C7 1.385(2)
C6 H6 0.982(18)
C7 H7 1.01(2)
C8 C7 1.378(2)
C8 C9 1.376(2)
C8 H8 0.989(19)
C9 H9 0.974(18)
C10 C9 1.3875(19)
C10 H10 0.959(16)
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
O H N2 4_565 0.88(2) 2.00(2) 2.8645(17) 166(2) yes
C10 H10 O 3_755 0.959(16) 2.566(16) 3.3198(17) 135.6(13) 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
C2 N1 N2 C1 0.35(16)
C3 N1 N2 C1 178.19(12)
N2 N1 C2 N3 -0.37(19)
C3 N1 C2 N3 -177.91(14)
C2 N1 C3 C4 94.22(18)
N2 N1 C3 C4 -83.09(15)
N1 N2 C1 N3 -0.24(19)
C1 N3 C2 N1 0.2(2)
N2 C1 N3 C2 0.0(2)
O C4 C3 N1 -69.27(14)
C5 C4 C3 N1 169.73(11)
C6 C5 C4 O 146.85(12)
C6 C5 C4 C3 -92.44(14)
C10 C5 C4 O -34.88(15)
C10 C5 C4 C3 85.83(14)
C4 C5 C6 C7 178.13(12)
C10 C5 C6 C7 -0.2(2)
C6 C5 C10 C9 0.30(19)
C4 C5 C10 C9 -177.99(12)
C5 C6 C7 C8 -0.2(2)
C9 C8 C7 C6 0.4(2)
C7 C8 C9 C10 -0.3(2)
C5 C10 C9 C8 -0.1(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8256736
