#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/58/4025893.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_4025893
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         'C19 H13 N3'
_chemical_formula_sum            'C19 H13 N3'
_chemical_formula_weight         283.32
_chemical_name_systematic
1-benzyl-4-(4-phenylbuta-1,3-diyn-1-yl)-4,5-dihydro-1H-1,2,3-triazole
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -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                102.3564(18)
_cell_angle_beta                 95.3363(18)
_cell_angle_gamma                91.0645(18)
_cell_formula_units_Z            2
_cell_length_a                   6.3632(8)
_cell_length_b                   7.9519(9)
_cell_length_c                   15.1874(18)
_cell_measurement_reflns_used    1653
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      23.78
_cell_measurement_theta_min      2.62
_cell_volume                     746.84(15)
_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 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0182
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5468
_diffrn_reflns_theta_full        26.39
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         2.62
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9879
_exptl_absorpt_correction_T_min  0.9556
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Bruker SHELXTL (Bruker, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3013
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0678
_refine_ls_R_factor_gt           0.0436
_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)+(0.0708P)²+0.0383P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1142
_refine_ls_wR_factor_ref         0.1274
_reflns_number_gt                2130
_reflns_number_total             3013
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo101870y_si_008.cif
_cod_data_source_block           10d
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_database_code               4025893
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.66741(18) 0.14376(15) 0.34949(8) 0.0358(3) Uani 1 1 d . . .
N2 N 0.5361(2) 0.23011(18) 0.40596(9) 0.0431(3) Uani 1 1 d . . .
N3 N 0.3640(2) 0.25328(18) 0.35710(9) 0.0447(4) Uani 1 1 d . . .
C1 C 0.3847(2) 0.1821(2) 0.26865(11) 0.0378(4) Uani 1 1 d . . .
C2 C 0.5781(2) 0.1119(2) 0.26411(11) 0.0443(4) Uani 1 1 d . . .
H2 H 0.6370 0.0529 0.2114 0.053 Uiso 1 1 calc R . .
C3 C 0.8758(2) 0.10103(19) 0.38550(11) 0.0399(4) Uani 1 1 d . . .
H3A H 0.9052 0.1670 0.4488 0.048 Uiso 1 1 calc R . .
H3B H 0.9833 0.1384 0.3498 0.048 Uiso 1 1 calc R . .
C4 C 0.2194(2) 0.1881(2) 0.19932(11) 0.0439(4) Uani 1 1 d . . .
C5 C 0.0778(3) 0.2001(2) 0.14380(12) 0.0459(4) Uani 1 1 d . . .
C6 C -0.0818(3) 0.2189(2) 0.07983(11) 0.0471(4) Uani 1 1 d . . .
C7 C -0.2207(3) 0.2417(2) 0.02506(11) 0.0464(4) Uani 1 1 d . . .
C11 C 0.8992(2) -0.08821(19) 0.38404(10) 0.0347(4) Uani 1 1 d . . .
C12 C 1.0840(2) -0.1660(2) 0.35889(11) 0.0415(4) Uani 1 1 d . . .
H12 H 1.1905 -0.1023 0.3387 0.050 Uiso 1 1 calc R . .
C13 C 1.1141(3) -0.3362(2) 0.36315(11) 0.0463(4) Uani 1 1 d . . .
H13 H 1.2421 -0.3883 0.3469 0.056 Uiso 1 1 calc R . .
C14 C 0.9589(3) -0.4303(2) 0.39083(11) 0.0470(4) Uani 1 1 d . . .
H14 H 0.9790 -0.5475 0.3929 0.056 Uiso 1 1 calc R . .
C15 C 0.7737(3) -0.3538(2) 0.41554(11) 0.0448(4) Uani 1 1 d . . .
H15 H 0.6665 -0.4183 0.4348 0.054 Uiso 1 1 calc R . .
C16 C 0.7448(2) -0.1830(2) 0.41218(10) 0.0389(4) Uani 1 1 d . . .
H16 H 0.6175 -0.1307 0.4294 0.047 Uiso 1 1 calc R . .
C21 C -0.3847(2) 0.2741(2) -0.04007(11) 0.0424(4) Uani 1 1 d . . .
C22 C -0.5898(3) 0.2107(2) -0.04111(11) 0.0466(4) Uani 1 1 d . . .
H22 H -0.6220 0.1426 0.0006 0.056 Uiso 1 1 calc R . .
C23 C -0.7473(3) 0.2465(2) -0.10280(12) 0.0516(5) Uani 1 1 d . . .
H23 H -0.8874 0.2025 -0.1034 0.062 Uiso 1 1 calc R . .
C24 C -0.7026(3) 0.3453(2) -0.16336(12) 0.0525(5) Uani 1 1 d . . .
H24 H -0.8116 0.3700 -0.2053 0.063 Uiso 1 1 calc R . .
C25 C -0.4997(3) 0.4082(2) -0.16288(12) 0.0565(5) Uani 1 1 d . . .
H25 H -0.4689 0.4758 -0.2050 0.068 Uiso 1 1 calc R . .
C26 C -0.3405(3) 0.3741(2) -0.10187(12) 0.0515(5) Uani 1 1 d . . .
H26 H -0.2009 0.4185 -0.1019 0.062 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 110.41(12) . . ?
C2 N1 C3 129.80(14) . . ?
N2 N1 C3 119.79(13) . . ?
N3 N2 N1 107.50(12) . . ?
N2 N3 C1 108.80(12) . . ?
N3 C1 C2 107.93(14) . . ?
N3 C1 C4 121.20(14) . . ?
C2 C1 C4 130.87(15) . . ?
N1 C2 C1 105.36(15) . . ?
N1 C3 C11 114.19(12) . . ?
C5 C4 C1 176.85(18) . . ?
C4 C5 C6 178.12(18) . . ?
C7 C6 C5 177.64(19) . . ?
C6 C7 C21 178.33(18) . . ?
C16 C11 C12 119.21(14) . . ?
C16 C11 C3 121.18(14) . . ?
C12 C11 C3 119.51(13) . . ?
C13 C12 C11 120.25(15) . . ?
C14 C13 C12 120.20(16) . . ?
C13 C14 C15 119.87(15) . . ?
C14 C15 C16 119.88(15) . . ?
C11 C16 C15 120.58(15) . . ?
C22 C21 C26 119.12(15) . . ?
C22 C21 C7 120.70(15) . . ?
C26 C21 C7 120.16(15) . . ?
C23 C22 C21 120.06(17) . . ?
C24 C23 C22 120.49(17) . . ?
C25 C24 C23 119.77(16) . . ?
C24 C25 C26 120.62(18) . . ?
C25 C26 C21 119.94(17) . . ?
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 1.3362(19) . ?
N1 N2 1.3445(18) . ?
N1 C3 1.4611(17) . ?
N2 N3 1.3034(17) . ?
N3 C1 1.361(2) . ?
C1 C2 1.362(2) . ?
C1 C4 1.426(2) . ?
C3 C11 1.511(2) . ?
C4 C5 1.196(2) . ?
C5 C6 1.372(2) . ?
C6 C7 1.200(2) . ?
C7 C21 1.435(2) . ?
C11 C16 1.381(2) . ?
C11 C12 1.386(2) . ?
C12 C13 1.385(2) . ?
C13 C14 1.377(2) . ?
C14 C15 1.382(2) . ?
C15 C16 1.385(2) . ?
C21 C22 1.388(2) . ?
C21 C26 1.397(2) . ?
C22 C23 1.383(2) . ?
C23 C24 1.377(3) . ?
C24 C25 1.375(3) . ?
C25 C26 1.379(2) . ?
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 0.03(17) . . . . ?
C3 N1 N2 N3 179.25(12) . . . . ?
N1 N2 N3 C1 -0.23(16) . . . . ?
N2 N3 C1 C2 0.34(18) . . . . ?
N2 N3 C1 C4 179.99(13) . . . . ?
N2 N1 C2 C1 0.17(18) . . . . ?
C3 N1 C2 C1 -178.95(14) . . . . ?
N3 C1 C2 N1 -0.30(18) . . . . ?
C4 C1 C2 N1 -179.91(15) . . . . ?
C2 N1 C3 C11 -72.0(2) . . . . ?
N2 N1 C3 C11 108.97(15) . . . . ?
N3 C1 C4 C5 27(3) . . . . ?
C2 C1 C4 C5 -154(3) . . . . ?
C1 C4 C5 C6 64(7) . . . . ?
C4 C5 C6 C7 -35(9) . . . . ?
C5 C6 C7 C21 20(10) . . . . ?
N1 C3 C11 C16 -45.0(2) . . . . ?
N1 C3 C11 C12 138.65(15) . . . . ?
C16 C11 C12 C13 -0.8(2) . . . . ?
C3 C11 C12 C13 175.55(14) . . . . ?
C11 C12 C13 C14 1.2(2) . . . . ?
C12 C13 C14 C15 -0.8(2) . . . . ?
C13 C14 C15 C16 0.1(2) . . . . ?
C12 C11 C16 C15 0.1(2) . . . . ?
C3 C11 C16 C15 -176.18(14) . . . . ?
C14 C15 C16 C11 0.2(2) . . . . ?
C6 C7 C21 C22 -137(6) . . . . ?
C6 C7 C21 C26 41(6) . . . . ?
C26 C21 C22 C23 0.1(2) . . . . ?
C7 C21 C22 C23 178.39(15) . . . . ?
C21 C22 C23 C24 -0.2(3) . . . . ?
C22 C23 C24 C25 0.4(3) . . . . ?
C23 C24 C25 C26 -0.4(3) . . . . ?
C24 C25 C26 C21 0.3(3) . . . . ?
C22 C21 C26 C25 -0.1(3) . . . . ?
C7 C21 C26 C25 -178.45(15) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 28578990
