#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/06/2230637.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_2230637
loop_
_publ_author_name
'Sarmiento-Sánchez, Juan I.'
'Aguirre, Gerardo'
'Rivero, Ignacio A.'
_publ_section_title
;
 1-Benzyl-4-(naphthalen-1-yl)-1H-1,2,3-triazole
;
_journal_coeditor_code           FL2334
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1856
_journal_paper_doi               10.1107/S1600536811019994
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C19 H15 N3'
_chemical_formula_moiety         'C19 H15 N3'
_chemical_formula_sum            'C19 H15 N3'
_chemical_formula_weight         285.34
_chemical_name_systematic
;
1-Benzyl-4-(naphthalen-1-yl)-1H-1,2,3-triazole
;
_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                 102.701(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.896(2)
_cell_length_b                   11.038(3)
_cell_length_c                   14.136(4)
_cell_measurement_reflns_used    36
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      12.43
_cell_measurement_theta_min      4.64
_cell_volume                     1506.3(7)
_computing_cell_refinement       'XSCANS (Siemens, 1996)'
_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_data_reduction        'XSCANS (Siemens, 1996)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2006)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       2θ/ω
_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  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0598
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3663
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.11
_diffrn_standards_decay_%        5.39
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             600
_exptl_crystal_size_max          .5
_exptl_crystal_size_mid          .48
_exptl_crystal_size_min          .28
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.168
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3471
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.1465
_refine_ls_R_factor_gt           0.0693
_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)+(0.0839P)²+0.3080P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1645
_refine_ls_wR_factor_ref         0.2017
_reflns_number_gt                1730
_reflns_number_total             3471
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fl2334.cif
_cod_data_source_block           I
_cod_original_cell_volume        1506.2(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2230637
_cod_database_fobs_code          2230637
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.2899(2) 0.3968(2) 0.18018(16) 0.0603(7) Uani d . 1 1 . .
N N2 0.3058(3) 0.2778(3) 0.19682(18) 0.0688(7) Uani d . 1 1 . .
N N3 0.4044(3) 0.2660(2) 0.27619(18) 0.0665(7) Uani d . 1 1 . .
C C1 0.5662(3) 0.4031(3) 0.39312(19) 0.0548(7) Uani d . 1 1 . .
C C2 0.6434(3) 0.5043(3) 0.3915(2) 0.0688(9) Uani d . 1 1 . .
H H2B 0.6208 0.5550 0.3377 0.083 Uiso calc R 1 1 . .
C C3 0.7552(4) 0.5365(3) 0.4664(2) 0.0779(10) Uani d . 1 1 . .
H H3B 0.8053 0.6066 0.4613 0.093 Uiso calc R 1 1 . .
C C4 0.7905(4) 0.4661(3) 0.5459(2) 0.0773(10) Uani d . 1 1 . .
H H4A 0.8655 0.4870 0.5954 0.093 Uiso calc R 1 1 . .
C C5 0.7114(3) 0.3581(3) 0.55387(19) 0.0592(8) Uani d . 1 1 . .
C C6 0.7469(4) 0.2850(3) 0.6363(2) 0.0756(10) Uani d . 1 1 . .
H H6A 0.8207 0.3068 0.6864 0.091 Uiso calc R 1 1 . .
C C7 0.6745(4) 0.1828(3) 0.6434(2) 0.0779(10) Uani d . 1 1 . .
H H7A 0.6995 0.1339 0.6981 0.093 Uiso calc R 1 1 . .
C C8 0.5616(3) 0.1501(3) 0.5686(2) 0.0726(9) Uani d . 1 1 . .
H H8A 0.5123 0.0799 0.5748 0.087 Uiso calc R 1 1 . .
C C9 0.5231(3) 0.2188(3) 0.4877(2) 0.0657(8) Uani d . 1 1 . .
H H9A 0.4475 0.1958 0.4394 0.079 Uiso calc R 1 1 . .
C C10 0.5991(3) 0.3282(2) 0.47587(18) 0.0519(7) Uani d . 1 1 . .
C C11 0.4501(3) 0.3772(3) 0.30902(19) 0.0530(7) Uani d . 1 1 . .
C C12 0.3770(3) 0.4599(3) 0.2479(2) 0.0627(8) Uani d . 1 1 . .
H H12A 0.3856 0.5438 0.2521 0.075 Uiso calc R 1 1 . .
C C13 0.1908(3) 0.4396(4) 0.0935(2) 0.0837(11) Uani d . 1 1 . .
H H13A 0.1334 0.3723 0.0644 0.100 Uiso calc R 1 1 . .
H H13B 0.2413 0.4688 0.0465 0.100 Uiso calc R 1 1 . .
C C14 0.0994(3) 0.5392(3) 0.11590(18) 0.0559(7) Uani d . 1 1 . .
C C15 0.1201(3) 0.6574(3) 0.0925(2) 0.0713(9) Uani d . 1 1 . .
H H15A 0.1931 0.6762 0.0634 0.086 Uiso calc R 1 1 . .
C C16 0.0351(4) 0.7485(3) 0.1112(2) 0.0768(10) Uani d . 1 1 . .
H H16A 0.0509 0.8280 0.0946 0.092 Uiso calc R 1 1 . .
C C17 -0.0723(3) 0.7230(3) 0.1539(2) 0.0687(9) Uani d . 1 1 . .
H H17A -0.1301 0.7846 0.1664 0.082 Uiso calc R 1 1 . .
C C18 -0.0945(3) 0.6056(3) 0.1783(2) 0.0680(9) Uani d . 1 1 . .
H H18A -0.1673 0.5875 0.2078 0.082 Uiso calc R 1 1 . .
C C19 -0.0089(3) 0.5140(3) 0.1592(2) 0.0617(8) Uani d . 1 1 . .
H H19A -0.0247 0.4345 0.1759 0.074 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 0.0033 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'
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
C12 N1 N2 . . 110.8(2) ?
C12 N1 C13 . . 129.6(3) ?
N2 N1 C13 . . 119.6(3) ?
N3 N2 N1 . . 106.4(2) ?
N2 N3 C11 . . 109.3(2) ?
C2 C1 C10 . . 117.9(3) ?
C2 C1 C11 . . 118.9(3) ?
C10 C1 C11 . . 123.2(3) ?
C1 C2 C3 . . 123.4(3) ?
C1 C2 H2B . . 118.3 ?
C3 C2 H2B . . 118.3 ?
C4 C3 C2 . . 120.1(3) ?
C4 C3 H3B . . 120.0 ?
C2 C3 H3B . . 120.0 ?
C3 C4 C5 . . 119.7(3) ?
C3 C4 H4A . . 120.1 ?
C5 C4 H4A . . 120.1 ?
C6 C5 C10 . . 121.6(3) ?
C6 C5 C4 . . 120.0(3) ?
C10 C5 C4 . . 118.4(3) ?
C7 C6 C5 . . 120.3(3) ?
C7 C6 H6A . . 119.9 ?
C5 C6 H6A . . 119.9 ?
C6 C7 C8 . . 120.3(3) ?
C6 C7 H7A . . 119.9 ?
C8 C7 H7A . . 119.9 ?
C9 C8 C7 . . 121.4(3) ?
C9 C8 H8A . . 119.3 ?
C7 C8 H8A . . 119.3 ?
C8 C9 C10 . . 120.4(3) ?
C8 C9 H9A . . 119.8 ?
C10 C9 H9A . . 119.8 ?
C1 C10 C5 . . 120.4(3) ?
C1 C10 C9 . . 123.5(3) ?
C5 C10 C9 . . 116.1(3) ?
C12 C11 N3 . . 107.6(2) ?
C12 C11 C1 . . 126.2(3) ?
N3 C11 C1 . . 126.1(3) ?
N1 C12 C11 . . 106.0(3) ?
N1 C12 H12A . . 127.0 ?
C11 C12 H12A . . 127.0 ?
N1 C13 C14 . . 112.5(2) ?
N1 C13 H13A . . 109.1 ?
C14 C13 H13A . . 109.1 ?
N1 C13 H13B . . 109.1 ?
C14 C13 H13B . . 109.1 ?
H13A C13 H13B . . 107.8 ?
C15 C14 C19 . . 118.1(3) ?
C15 C14 C13 . . 121.1(3) ?
C19 C14 C13 . . 120.7(3) ?
C14 C15 C16 . . 121.4(3) ?
C14 C15 H15A . . 119.3 ?
C16 C15 H15A . . 119.3 ?
C17 C16 C15 . . 120.2(3) ?
C17 C16 H16A . . 119.9 ?
C15 C16 H16A . . 119.9 ?
C16 C17 C18 . . 119.4(3) ?
C16 C17 H17A . . 120.3 ?
C18 C17 H17A . . 120.3 ?
C17 C18 C19 . . 120.2(3) ?
C17 C18 H18A . . 119.9 ?
C19 C18 H18A . . 119.9 ?
C14 C19 C18 . . 120.7(3) ?
C14 C19 H19A . . 119.7 ?
C18 C19 H19A . . 119.7 ?
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 C12 . 1.335(3) ?
N1 N2 . 1.337(3) ?
N1 C13 . 1.470(3) ?
N2 N3 . 1.321(3) ?
N3 C11 . 1.353(3) ?
C1 C2 . 1.357(4) ?
C1 C10 . 1.410(4) ?
C1 C11 . 1.488(4) ?
C2 C3 . 1.399(4) ?
C2 H2B . 0.9300 ?
C3 C4 . 1.348(4) ?
C3 H3B . 0.9300 ?
C4 C5 . 1.444(5) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.397(4) ?
C5 C10 . 1.421(4) ?
C6 C7 . 1.352(5) ?
C6 H6A . 0.9300 ?
C7 C8 . 1.407(5) ?
C7 H7A . 0.9300 ?
C8 C9 . 1.356(4) ?
C8 H8A . 0.9300 ?
C9 C10 . 1.452(4) ?
C9 H9A . 0.9300 ?
C11 C12 . 1.353(4) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.500(4) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 C15 . 1.372(4) ?
C14 C19 . 1.375(4) ?
C15 C16 . 1.374(5) ?
C15 H15A . 0.9300 ?
C16 C17 . 1.363(5) ?
C16 H16A . 0.9300 ?
C17 C18 . 1.371(4) ?
C17 H17A . 0.9300 ?
C18 C19 . 1.384(4) ?
C18 H18A . 0.9300 ?
C19 H19A . 0.9300 ?
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
C12 N1 N2 N3 . . . . 0.0(3) ?
C13 N1 N2 N3 . . . . 177.3(2) ?
N1 N2 N3 C11 . . . . -0.1(3) ?
C10 C1 C2 C3 . . . . 1.4(5) ?
C11 C1 C2 C3 . . . . -179.5(3) ?
C1 C2 C3 C4 . . . . -0.6(5) ?
C2 C3 C4 C5 . . . . -0.7(5) ?
C3 C4 C5 C6 . . . . -179.7(3) ?
C3 C4 C5 C10 . . . . 1.1(5) ?
C10 C5 C6 C7 . . . . 0.2(5) ?
C4 C5 C6 C7 . . . . -179.0(3) ?
C5 C6 C7 C8 . . . . -0.9(5) ?
C6 C7 C8 C9 . . . . 0.5(5) ?
C7 C8 C9 C10 . . . . 0.6(5) ?
C2 C1 C10 C5 . . . . -1.0(4) ?
C11 C1 C10 C5 . . . . -179.9(2) ?
C2 C1 C10 C9 . . . . 178.7(3) ?
C11 C1 C10 C9 . . . . -0.2(4) ?
C6 C5 C10 C1 . . . . -179.5(3) ?
C4 C5 C10 C1 . . . . -0.3(4) ?
C6 C5 C10 C9 . . . . 0.8(4) ?
C4 C5 C10 C9 . . . . -180.0(3) ?
C8 C9 C10 C1 . . . . 179.1(3) ?
C8 C9 C10 C5 . . . . -1.2(4) ?
N2 N3 C11 C12 . . . . 0.1(3) ?
N2 N3 C11 C1 . . . . -176.1(2) ?
C2 C1 C11 C12 . . . . -27.0(4) ?
C10 C1 C11 C12 . . . . 151.9(3) ?
C2 C1 C11 N3 . . . . 148.4(3) ?
C10 C1 C11 N3 . . . . -32.6(4) ?
N2 N1 C12 C11 . . . . 0.1(3) ?
C13 N1 C12 C11 . . . . -176.9(3) ?
N3 C11 C12 N1 . . . . -0.1(3) ?
C1 C11 C12 N1 . . . . 176.0(2) ?
C12 N1 C13 C14 . . . . -50.4(4) ?
N2 N1 C13 C14 . . . . 132.8(3) ?
N1 C13 C14 C15 . . . . 104.8(3) ?
N1 C13 C14 C19 . . . . -76.2(4) ?
C19 C14 C15 C16 . . . . -0.3(4) ?
C13 C14 C15 C16 . . . . 178.7(3) ?
C14 C15 C16 C17 . . . . 0.1(5) ?
C15 C16 C17 C18 . . . . 0.2(5) ?
C16 C17 C18 C19 . . . . -0.3(5) ?
C15 C14 C19 C18 . . . . 0.2(4) ?
C13 C14 C19 C18 . . . . -178.8(3) ?
C17 C18 C19 C14 . . . . 0.1(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30656764
