#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/58/4025887.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4025887
loop_
_publ_author_name
'Thanh Luu'
'Boris J. Medos'
'Erin R. Graham'
'Danielle M. Vallee'
'Robert McDonald'
'Michael J. Ferguson'
'Rik R. Tykwinski'
_publ_contact_author_address
; Department of Chemistry
  University of Alberta
  Edmonton, Alberta T6G 2G2
  Canada
;
_publ_contact_author_email       rik.tykwinski@ualberta.ca
_publ_contact_author_fax         1(780)4928231
_publ_contact_author_name        'Dr Rik R. Tykwinski'
_publ_contact_author_phone       1(780)4925307
_publ_section_title
;
 Reactions of Terminal Polyynes with Benzyl Azide
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8498
_journal_page_last               8507
_journal_paper_doi               10.1021/jo101870y
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C17 H13 N3'
_chemical_formula_sum            'C17 H13 N3'
_chemical_formula_weight         259.30
_chemical_name_systematic
1-benzyl-4-(phenylethynyl)-4,5-dihydro-1H-1,2,3-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           'manual editing of SHELXL template'
_cell_angle_alpha                90.00
_cell_angle_beta                 93.6141(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.7277(8)
_cell_length_b                   14.2042(18)
_cell_length_c                   16.811(2)
_cell_measurement_reflns_used    2355
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      23.39
_cell_measurement_theta_min      2.43
_cell_volume                     1365.0(3)
_computing_cell_refinement       'Bruker SAINT (Bruker, 1997)'
_computing_data_collection       'Bruker SMART (Bruker, 1997)'
_computing_data_reduction        'Bruker SAINT (Bruker, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL (Bruker, 1997)'
_computing_publication_material  'Bruker SHELXTL (Bruker, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type
'Bruker PLATFORM diffractometer/SMART 1000 CCD area detector'
_diffrn_measurement_method       '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  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0242
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7513
_diffrn_reflns_theta_full        26.40
_diffrn_reflns_theta_max         26.40
_diffrn_reflns_theta_min         1.88
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9788
_exptl_absorpt_correction_T_min  0.9496
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2800
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0409
_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)+(0.0647P)²+0.0711P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1147
_reflns_number_gt                2030
_reflns_number_total             2800
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo101870y_si_001.cif
_cod_data_source_block           3c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4025887
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.00505(19) 0.40375(7) 0.29181(6) 0.0439(3) Uani 1 1 d . . .
N2 N 0.2369(2) 0.38886(8) 0.29794(7) 0.0531(3) Uani 1 1 d . . .
N3 N 0.3084(2) 0.38426(8) 0.22549(7) 0.0530(3) Uani 1 1 d . . .
C1 C 0.1192(2) 0.39656(9) 0.17290(8) 0.0432(3) Uani 1 1 d . . .
C2 C -0.0743(2) 0.40902(9) 0.21533(8) 0.0442(3) Uani 1 1 d . . .
H2 H -0.2307 0.4192 0.1950 0.053 Uiso 1 1 calc R . .
C3 C -0.1223(3) 0.41675(10) 0.36350(8) 0.0500(4) Uani 1 1 d . . .
H3A H -0.0444 0.3799 0.4076 0.060 Uiso 1 1 calc R . .
H3B H -0.2830 0.3919 0.3537 0.060 Uiso 1 1 calc R . .
C4 C 0.1443(2) 0.39251(9) 0.08887(8) 0.0473(3) Uani 1 1 d . . .
C5 C 0.1821(2) 0.38473(9) 0.02009(9) 0.0475(3) Uani 1 1 d . . .
C11 C -0.1354(2) 0.51863(9) 0.38860(7) 0.0429(3) Uani 1 1 d . . .
C12 C 0.0423(3) 0.58234(10) 0.37772(8) 0.0528(4) Uani 1 1 d . . .
H12 H 0.1779 0.5625 0.3526 0.063 Uiso 1 1 calc R . .
C13 C 0.0250(3) 0.67436(11) 0.40298(9) 0.0599(4) Uani 1 1 d . . .
H13 H 0.1474 0.7177 0.3945 0.072 Uiso 1 1 calc R . .
C14 C -0.1690(3) 0.70350(11) 0.44037(8) 0.0616(4) Uani 1 1 d . . .
H14 H -0.1800 0.7666 0.4585 0.074 Uiso 1 1 calc R . .
C15 C -0.3465(3) 0.64106(12) 0.45142(9) 0.0642(4) Uani 1 1 d . . .
H15 H -0.4809 0.6610 0.4772 0.077 Uiso 1 1 calc R . .
C16 C -0.3305(3) 0.54912(11) 0.42517(8) 0.0547(4) Uani 1 1 d . . .
H16 H -0.4552 0.5065 0.4324 0.066 Uiso 1 1 calc R . .
C21 C 0.2355(2) 0.37121(9) -0.06155(8) 0.0444(3) Uani 1 1 d . . .
C22 C 0.0835(3) 0.32170(10) -0.11388(8) 0.0528(4) Uani 1 1 d . . .
H22 H -0.0596 0.2981 -0.0963 0.063 Uiso 1 1 calc R . .
C23 C 0.1404(3) 0.30669(10) -0.19163(9) 0.0592(4) Uani 1 1 d . . .
H23 H 0.0354 0.2729 -0.2272 0.071 Uiso 1 1 calc R . .
C24 C 0.3470(3) 0.34008(10) -0.21806(8) 0.0551(4) Uani 1 1 d . . .
H24 H 0.3847 0.3296 -0.2716 0.066 Uiso 1 1 calc R . .
C25 C 0.4996(3) 0.38905(10) -0.16629(9) 0.0543(4) Uani 1 1 d . . .
H25 H 0.6427 0.4122 -0.1842 0.065 Uiso 1 1 calc R . .
C26 C 0.4447(3) 0.40439(10) -0.08879(8) 0.0511(4) Uani 1 1 d . . .
H26 H 0.5508 0.4380 -0.0535 0.061 Uiso 1 1 calc R . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 N2 110.91(11) . . ?
C2 N1 C3 129.00(12) . . ?
N2 N1 C3 120.00(11) . . ?
N3 N2 N1 107.58(10) . . ?
N2 N3 C1 108.26(11) . . ?
N3 C1 C2 108.37(12) . . ?
N3 C1 C4 120.59(12) . . ?
C2 C1 C4 131.01(13) . . ?
N1 C2 C1 104.88(12) . . ?
N1 C3 C11 112.84(10) . . ?
C5 C4 C1 174.45(14) . . ?
C4 C5 C21 176.95(14) . . ?
C16 C11 C12 118.52(13) . . ?
C16 C11 C3 118.79(12) . . ?
C12 C11 C3 122.69(12) . . ?
C13 C12 C11 120.77(14) . . ?
C14 C13 C12 120.12(15) . . ?
C15 C14 C13 119.68(15) . . ?
C14 C15 C16 120.18(15) . . ?
C11 C16 C15 120.72(15) . . ?
C22 C21 C26 118.77(13) . . ?
C22 C21 C5 120.63(12) . . ?
C26 C21 C5 120.55(12) . . ?
C23 C22 C21 120.07(13) . . ?
C24 C23 C22 120.72(14) . . ?
C23 C24 C25 119.56(13) . . ?
C26 C25 C24 120.19(14) . . ?
C25 C26 C21 120.69(13) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.3384(17) . ?
N1 N2 1.3423(15) . ?
N1 C3 1.4593(16) . ?
N2 N3 1.3109(16) . ?
N3 C1 1.3660(18) . ?
C1 C2 1.3666(18) . ?
C1 C4 1.4301(18) . ?
C3 C11 1.5105(19) . ?
C4 C5 1.1948(18) . ?
C5 C21 1.4378(18) . ?
C11 C16 1.3786(18) . ?
C11 C12 1.3827(19) . ?
C12 C13 1.380(2) . ?
C13 C14 1.375(2) . ?
C14 C15 1.371(2) . ?
C15 C16 1.383(2) . ?
C21 C22 1.3892(19) . ?
C21 C26 1.392(2) . ?
C22 C23 1.3833(19) . ?
C23 C24 1.375(2) . ?
C24 C25 1.382(2) . ?
C25 C26 1.3768(19) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 N2 N3 -0.12(14) . . . . ?
C3 N1 N2 N3 -176.94(10) . . . . ?
N1 N2 N3 C1 0.10(14) . . . . ?
N2 N3 C1 C2 -0.04(15) . . . . ?
N2 N3 C1 C4 -178.39(10) . . . . ?
N2 N1 C2 C1 0.09(14) . . . . ?
C3 N1 C2 C1 176.55(11) . . . . ?
N3 C1 C2 N1 -0.03(14) . . . . ?
C4 C1 C2 N1 178.09(12) . . . . ?
C2 N1 C3 C11 -86.05(16) . . . . ?
N2 N1 C3 C11 90.13(14) . . . . ?
N3 C1 C4 C5 22.9(15) . . . . ?
C2 C1 C4 C5 -155.1(14) . . . . ?
C1 C4 C5 C21 19(4) . . . . ?
N1 C3 C11 C16 147.67(13) . . . . ?
N1 C3 C11 C12 -33.54(18) . . . . ?
C16 C11 C12 C13 0.1(2) . . . . ?
C3 C11 C12 C13 -178.71(13) . . . . ?
C11 C12 C13 C14 0.8(2) . . . . ?
C12 C13 C14 C15 -0.9(2) . . . . ?
C13 C14 C15 C16 0.1(2) . . . . ?
C12 C11 C16 C15 -0.9(2) . . . . ?
C3 C11 C16 C15 177.92(13) . . . . ?
C14 C15 C16 C11 0.9(2) . . . . ?
C4 C5 C21 C22 98(3) . . . . ?
C4 C5 C21 C26 -80(3) . . . . ?
C26 C21 C22 C23 -0.4(2) . . . . ?
C5 C21 C22 C23 -178.02(12) . . . . ?
C21 C22 C23 C24 0.2(2) . . . . ?
C22 C23 C24 C25 0.1(2) . . . . ?
C23 C24 C25 C26 -0.1(2) . . . . ?
C24 C25 C26 C21 -0.2(2) . . . . ?
C22 C21 C26 C25 0.4(2) . . . . ?
C5 C21 C26 C25 178.02(12) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 28579008
