#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/58/4025892.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_4025892
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
; Friedrich-Alexander-Universitat Erlangen
  Department Chemie und Pharmazie
  Geschaftsstelle
  Egerlandstr. 3
  91058 Erlangen
  Germany
;
_publ_contact_author_email       rik.tykwinski@chemie.uni-erlangen.de
_publ_contact_author_fax         +49(9131)8522540
_publ_contact_author_name        'Dr. Rik R. Tykwinski'
_publ_contact_author_phone       +49(9131)8526865
_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         'C18 H13 N3 O'
_chemical_formula_sum            'C18 H13 N3 O'
_chemical_formula_weight         287.31
_chemical_name_systematic
3-(1-benzyl-1H-1,2,3-triazol-4-yl)-1-phenylprop-2-yn-1-one
_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           SHELXL-97
_cell_angle_alpha                70.6508(19)
_cell_angle_beta                 79.5467(19)
_cell_angle_gamma                68.0695(19)
_cell_formula_units_Z            2
_cell_length_a                   7.8486(8)
_cell_length_b                   8.8827(9)
_cell_length_c                   12.1321(13)
_cell_measurement_reflns_used    1190
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      20.71
_cell_measurement_theta_min      2.68
_cell_volume                     738.68(13)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0413
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5108
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.78
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9918
_exptl_absorpt_correction_T_min  0.9692
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'Bruker SHELXTL (Bruker, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2608
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0428
_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)+(0.0609P)²+0.0246P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1208
_reflns_number_gt                1724
_reflns_number_total             2608
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo101870y_si_007.cif
_cod_data_source_block           3p
_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               4025892
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
O O -0.1918(2) 0.39757(17) -0.19979(12) 0.0610(4) Uani 1 1 d . . .
N1 N 0.14450(19) -0.05780(19) 0.33464(13) 0.0456(4) Uani 1 1 d . . .
N2 N 0.1039(2) 0.0865(2) 0.36350(14) 0.0544(4) Uani 1 1 d . . .
N3 N 0.0330(2) 0.2125(2) 0.27262(15) 0.0531(4) Uani 1 1 d . . .
C1 C 0.0308(2) 0.1478(2) 0.18586(16) 0.0446(5) Uani 1 1 d . . .
C2 C 0.1023(2) -0.0251(2) 0.22563(16) 0.0469(5) Uani 1 1 d . . .
H2 H 0.1183 -0.1044 0.1846 0.056 Uiso 1 1 calc R . .
C3 C 0.2328(3) -0.2224(2) 0.41865(16) 0.0517(5) Uani 1 1 d . . .
H3A H 0.1996 -0.3111 0.4043 0.062 Uiso 1 1 calc R . .
H3B H 0.1859 -0.2168 0.4992 0.062 Uiso 1 1 calc R . .
C4 C -0.0449(3) 0.2542(2) 0.07757(18) 0.0494(5) Uani 1 1 d . . .
C5 C -0.1147(3) 0.3447(2) -0.01161(18) 0.0497(5) Uani 1 1 d . . .
C6 C -0.2167(3) 0.4499(2) -0.11472(16) 0.0460(5) Uani 1 1 d . . .
C11 C 0.4392(2) -0.2698(2) 0.40847(14) 0.0413(5) Uani 1 1 d . . .
C12 C 0.5449(3) -0.3640(2) 0.33413(16) 0.0490(5) Uani 1 1 d . . .
H12 H 0.4870 -0.3986 0.2893 0.059 Uiso 1 1 calc R . .
C13 C 0.7344(3) -0.4079(3) 0.32478(17) 0.0580(6) Uani 1 1 d . . .
H13 H 0.8062 -0.4715 0.2729 0.070 Uiso 1 1 calc R . .
C14 C 0.8186(3) -0.3601(3) 0.38987(18) 0.0601(6) Uani 1 1 d . . .
H14 H 0.9489 -0.3914 0.3837 0.072 Uiso 1 1 calc R . .
C15 C 0.7160(3) -0.2672(3) 0.46390(18) 0.0613(6) Uani 1 1 d . . .
H15 H 0.7749 -0.2342 0.5093 0.074 Uiso 1 1 calc R . .
C16 C 0.5258(3) -0.2211(2) 0.47263(16) 0.0521(5) Uani 1 1 d . . .
H16 H 0.4547 -0.1553 0.5234 0.063 Uiso 1 1 calc R . .
C21 C -0.3523(2) 0.6161(2) -0.10947(15) 0.0408(4) Uani 1 1 d . . .
C22 C -0.3918(3) 0.6649(2) -0.00826(16) 0.0469(5) Uani 1 1 d . . .
H22 H -0.3280 0.5922 0.0597 0.056 Uiso 1 1 calc R . .
C23 C -0.5239(3) 0.8193(3) -0.00548(19) 0.0576(6) Uani 1 1 d . . .
H23 H -0.5520 0.8521 0.0645 0.069 Uiso 1 1 calc R . .
C24 C -0.6148(3) 0.9255(3) -0.1048(2) 0.0659(6) Uani 1 1 d . . .
H24 H -0.7050 1.0319 -0.1032 0.079 Uiso 1 1 calc R . .
C25 C -0.5751(3) 0.8778(3) -0.20599(19) 0.0641(6) Uani 1 1 d . . .
H25 H -0.6372 0.9517 -0.2743 0.077 Uiso 1 1 calc R . .
C26 C -0.4458(3) 0.7235(3) -0.20858(16) 0.0535(5) Uani 1 1 d . . .
H26 H -0.4202 0.6902 -0.2783 0.064 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 N2 111.23(15) . . ?
C2 N1 C3 129.01(16) . . ?
N2 N1 C3 119.69(15) . . ?
N3 N2 N1 106.97(14) . . ?
N2 N3 C1 108.59(15) . . ?
N3 C1 C2 108.47(16) . . ?
N3 C1 C4 121.51(17) . . ?
C2 C1 C4 129.95(18) . . ?
N1 C2 C1 104.73(17) . . ?
N1 C3 C11 111.72(14) . . ?
C5 C4 C1 177.7(2) . . ?
C4 C5 C6 173.9(2) . . ?
O C6 C5 119.92(18) . . ?
O C6 C21 122.87(17) . . ?
C5 C6 C21 117.18(16) . . ?
C16 C11 C12 118.89(18) . . ?
C16 C11 C3 120.92(17) . . ?
C12 C11 C3 120.19(17) . . ?
C11 C12 C13 120.28(18) . . ?
C14 C13 C12 120.19(19) . . ?
C13 C14 C15 120.2(2) . . ?
C14 C15 C16 119.87(19) . . ?
C11 C16 C15 120.57(18) . . ?
C22 C21 C26 119.49(17) . . ?
C22 C21 C6 121.78(17) . . ?
C26 C21 C6 118.70(16) . . ?
C21 C22 C23 120.21(19) . . ?
C24 C23 C22 119.8(2) . . ?
C25 C24 C23 120.2(2) . . ?
C26 C25 C24 120.2(2) . . ?
C25 C26 C21 120.15(19) . . ?
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
O C6 1.224(2) . ?
N1 C2 1.332(2) . ?
N1 N2 1.349(2) . ?
N1 C3 1.472(2) . ?
N2 N3 1.310(2) . ?
N3 C1 1.361(2) . ?
C1 C2 1.367(3) . ?
C1 C4 1.419(3) . ?
C3 C11 1.507(2) . ?
C4 C5 1.194(3) . ?
C5 C6 1.452(3) . ?
C6 C21 1.476(3) . ?
C11 C16 1.375(2) . ?
C11 C12 1.382(2) . ?
C12 C13 1.383(3) . ?
C13 C14 1.364(3) . ?
C14 C15 1.367(3) . ?
C15 C16 1.386(3) . ?
C21 C22 1.381(2) . ?
C21 C26 1.390(2) . ?
C22 C23 1.383(3) . ?
C23 C24 1.381(3) . ?
C24 C25 1.376(3) . ?
C25 C26 1.373(3) . ?
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 0.8(2) . . . . ?
C3 N1 N2 N3 177.95(14) . . . . ?
N1 N2 N3 C1 -0.7(2) . . . . ?
N2 N3 C1 C2 0.4(2) . . . . ?
N2 N3 C1 C4 177.64(16) . . . . ?
N2 N1 C2 C1 -0.5(2) . . . . ?
C3 N1 C2 C1 -177.34(16) . . . . ?
N3 C1 C2 N1 0.1(2) . . . . ?
C4 C1 C2 N1 -176.85(18) . . . . ?
C2 N1 C3 C11 90.3(2) . . . . ?
N2 N1 C3 C11 -86.27(19) . . . . ?
N3 C1 C4 C5 -71(5) . . . . ?
C2 C1 C4 C5 105(5) . . . . ?
C1 C4 C5 C6 -27(6) . . . . ?
C4 C5 C6 O -98.8(19) . . . . ?
C4 C5 C6 C21 79.3(19) . . . . ?
N1 C3 C11 C16 89.3(2) . . . . ?
N1 C3 C11 C12 -90.8(2) . . . . ?
C16 C11 C12 C13 0.0(3) . . . . ?
C3 C11 C12 C13 -179.91(17) . . . . ?
C11 C12 C13 C14 0.7(3) . . . . ?
C12 C13 C14 C15 -0.6(3) . . . . ?
C13 C14 C15 C16 -0.1(3) . . . . ?
C12 C11 C16 C15 -0.7(3) . . . . ?
C3 C11 C16 C15 179.17(16) . . . . ?
C14 C15 C16 C11 0.8(3) . . . . ?
O C6 C21 C22 173.07(17) . . . . ?
C5 C6 C21 C22 -4.9(3) . . . . ?
O C6 C21 C26 -5.2(3) . . . . ?
C5 C6 C21 C26 176.87(16) . . . . ?
C26 C21 C22 C23 0.2(3) . . . . ?
C6 C21 C22 C23 -177.96(17) . . . . ?
C21 C22 C23 C24 -0.8(3) . . . . ?
C22 C23 C24 C25 0.4(3) . . . . ?
C23 C24 C25 C26 0.5(3) . . . . ?
C24 C25 C26 C21 -1.1(3) . . . . ?
C22 C21 C26 C25 0.7(3) . . . . ?
C6 C21 C26 C25 178.92(18) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 13095035
