#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/43/2234320.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_2234320
loop_
_publ_author_name
'Selvarathy Grace, P.'
'Jebas, Samuel Robinson'
'Ravindran Durai Nayagam, B.'
'Schollmeyer, Dieter'
_publ_section_title
;
 1-Benzyl-1H-benzotriazole
;
_journal_coeditor_code           LH5426
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1132
_journal_paper_doi               10.1107/S1600536812010951
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C13 H11 N3'
_chemical_formula_moiety         'C13 H11 N3'
_chemical_formula_sum            'C13 H11 N3'
_chemical_formula_weight         209.25
_chemical_name_systematic
;
1-Benzyl-1H-benzotriazole
;
_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                 106.490(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.5734(10)
_cell_length_b                   5.9705(4)
_cell_length_c                   16.1202(14)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      68
_cell_measurement_theta_min      55
_cell_volume                     1068.07(15)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction
'CORINC (Dräger & Gattow, 1971; Wiehl & Schollmeyer, 1994)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1080
_diffrn_reflns_av_sigmaI/netI    0.0394
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            2125
_diffrn_reflns_theta_full        70.00
_diffrn_reflns_theta_max         70.00
_diffrn_reflns_theta_min         3.98
_diffrn_standards_decay_%        2
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.635
_exptl_absorpt_correction_T_max  0.9392
_exptl_absorpt_correction_T_min  0.8324
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
(CORINC; Dräger & Gattow, 1971; Wiehl & Schollmeyer,
1994)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.302
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2020
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0620
_refine_ls_R_factor_gt           0.0549
_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)+(0.0628P)²+0.3976P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1338
_refine_ls_wR_factor_ref         0.1381
_reflns_number_gt                1788
_reflns_number_total             2020
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh5426.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2234320
_cod_database_fobs_code          2234320
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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
N N1 0.42315(15) 0.1763(3) 0.37392(11) 0.0331(4) Uani d . 1 1
N N2 0.40768(14) 0.2958(3) 0.30376(10) 0.0312(4) Uani d . 1 1
N N3 0.35886(13) 0.4957(3) 0.31508(10) 0.0255(4) Uani d . 1 1
C C4 0.34149(14) 0.5049(3) 0.39488(11) 0.0232(4) Uani d . 1 1
C C5 0.29338(17) 0.6694(3) 0.43720(12) 0.0291(4) Uani d . 1 1
H H5 0.2638 0.8079 0.4105 0.035 Uiso calc R 1 1
C C6 0.29158(18) 0.6177(4) 0.52002(13) 0.0345(5) Uani d . 1 1
H H6 0.2588 0.7231 0.5513 0.041 Uiso calc R 1 1
C C7 0.33691(17) 0.4130(4) 0.55981(12) 0.0332(5) Uani d . 1 1
H H7 0.3349 0.3858 0.6174 0.040 Uiso calc R 1 1
C C8 0.38387(17) 0.2517(4) 0.51801(13) 0.0324(5) Uani d . 1 1
H H8 0.4147 0.1145 0.5453 0.039 Uiso calc R 1 1
C C9 0.38385(15) 0.3007(3) 0.43252(12) 0.0256(4) Uani d . 1 1
C C10 0.33293(16) 0.6650(3) 0.24689(12) 0.0300(4) Uani d . 1 1
H H10A 0.3745 0.6244 0.2031 0.036 Uiso calc R 1 1
H H10B 0.3648 0.8114 0.2721 0.036 Uiso calc R 1 1
C C11 0.19948(16) 0.6862(3) 0.20336(11) 0.0254(4) Uani d . 1 1
C C12 0.13833(19) 0.8816(3) 0.21182(13) 0.0343(5) Uani d . 1 1
H H12 0.1804 1.0015 0.2461 0.041 Uiso calc R 1 1
C C13 0.0167(2) 0.9019(4) 0.17048(15) 0.0425(5) Uani d . 1 1
H H13 -0.0246 1.0354 0.1769 0.051 Uiso calc R 1 1
C C14 -0.04510(19) 0.7302(4) 0.12006(15) 0.0434(6) Uani d . 1 1
H H14 -0.1285 0.7459 0.0912 0.052 Uiso calc R 1 1
C C15 0.01477(19) 0.5340(4) 0.11147(13) 0.0376(5) Uani d . 1 1
H H15 -0.0276 0.4148 0.0769 0.045 Uiso calc R 1 1
C C16 0.13627(17) 0.5127(3) 0.15333(12) 0.0310(4) Uani d . 1 1
H H16 0.1769 0.3778 0.1478 0.037 Uiso calc R 1 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 '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
N2 N1 C9 108.00(16)
N1 N2 N3 108.93(15)
N2 N3 C4 110.05(15)
N2 N3 C10 120.85(15)
C4 N3 C10 129.11(15)
N3 C4 C9 104.45(16)
N3 C4 C5 132.60(17)
C9 C4 C5 122.94(17)
C6 C5 C4 115.70(18)
C6 C5 H5 122.2
C4 C5 H5 122.2
C5 C6 C7 121.96(19)
C5 C6 H6 119.0
C7 C6 H6 119.0
C8 C7 C6 122.18(18)
C8 C7 H7 118.9
C6 C7 H7 118.9
C7 C8 C9 116.38(18)
C7 C8 H8 121.8
C9 C8 H8 121.8
N1 C9 C4 108.56(16)
N1 C9 C8 130.63(18)
C4 C9 C8 120.80(18)
N3 C10 C11 111.88(15)
N3 C10 H10A 109.2
C11 C10 H10A 109.2
N3 C10 H10B 109.2
C11 C10 H10B 109.2
H10A C10 H10B 107.9
C16 C11 C12 118.97(18)
C16 C11 C10 120.57(17)
C12 C11 C10 120.46(18)
C13 C12 C11 120.2(2)
C13 C12 H12 119.9
C11 C12 H12 119.9
C14 C13 C12 120.5(2)
C14 C13 H13 119.8
C12 C13 H13 119.8
C13 C14 C15 119.8(2)
C13 C14 H14 120.1
C15 C14 H14 120.1
C16 C15 C14 119.8(2)
C16 C15 H15 120.1
C14 C15 H15 120.1
C15 C16 C11 120.71(19)
C15 C16 H16 119.6
C11 C16 H16 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 N2 1.306(2)
N1 C9 1.376(2)
N2 N3 1.354(2)
N3 C4 1.358(2)
N3 C10 1.460(2)
C4 C9 1.388(3)
C4 C5 1.399(3)
C5 C6 1.376(3)
C5 H5 0.9500
C6 C7 1.411(3)
C6 H6 0.9500
C7 C8 1.373(3)
C7 H7 0.9500
C8 C9 1.409(3)
C8 H8 0.9500
C10 C11 1.509(2)
C10 H10A 0.9900
C10 H10B 0.9900
C11 C16 1.387(3)
C11 C12 1.391(3)
C12 C13 1.382(3)
C12 H12 0.9500
C13 C14 1.376(3)
C13 H13 0.9500
C14 C15 1.388(3)
C14 H14 0.9500
C15 C16 1.382(3)
C15 H15 0.9500
C16 H16 0.9500
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
C8 H8 N1 3_656 0.95 2.62 3.513(3) 158
C14 H14 Cg 2_555 0.95 2.69 3.583(2) 157
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
C9 N1 N2 N3 -0.1(2)
N1 N2 N3 C4 -0.4(2)
N1 N2 N3 C10 179.31(15)
N2 N3 C4 C9 0.78(18)
C10 N3 C4 C9 -178.94(17)
N2 N3 C4 C5 -179.12(18)
C10 N3 C4 C5 1.2(3)
N3 C4 C5 C6 -179.41(18)
C9 C4 C5 C6 0.7(3)
C4 C5 C6 C7 0.8(3)
C5 C6 C7 C8 -1.0(3)
C6 C7 C8 C9 -0.4(3)
N2 N1 C9 C4 0.6(2)
N2 N1 C9 C8 -178.05(18)
N3 C4 C9 N1 -0.84(19)
C5 C4 C9 N1 179.07(17)
N3 C4 C9 C8 177.98(16)
C5 C4 C9 C8 -2.1(3)
C7 C8 C9 N1 -179.62(19)
C7 C8 C9 C4 1.9(3)
N2 N3 C10 C11 106.88(18)
C4 N3 C10 C11 -73.4(2)
N3 C10 C11 C16 -67.4(2)
N3 C10 C11 C12 113.53(19)
C16 C11 C12 C13 -0.3(3)
C10 C11 C12 C13 178.74(17)
C11 C12 C13 C14 -0.5(3)
C12 C13 C14 C15 0.8(3)
C13 C14 C15 C16 -0.3(3)
C14 C15 C16 C11 -0.5(3)
C12 C11 C16 C15 0.9(3)
C10 C11 C16 C15 -178.22(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 454643
