#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:40:35 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178437 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/58/4025888.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_4025888
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         'C15 H11 N3 S'
_chemical_formula_sum            'C15 H11 N3 S'
_chemical_formula_weight         265.33
_chemical_name_systematic        1-benzyl-4-(2-thienylethynyl)-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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.4178(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9330(10)
_cell_length_b                   5.7873(6)
_cell_length_c                   23.287(2)
_cell_measurement_reflns_used    4460
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      26.33
_cell_measurement_theta_min      2.43
_cell_volume                     1312.2(2)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0180
_diffrn_reflns_av_sigmaI/netI    0.0220
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            6037
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.78
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_T_max  0.9545
_exptl_absorpt_correction_T_min  0.8381
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.78
_exptl_crystal_size_mid          0.65
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.652
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         2672
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0456
_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)+(0.0482P)²+0.9640P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1209
_reflns_number_gt                2254
_reflns_number_total             2672
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo101870y_si_002.cif
_cod_data_source_block           3e
_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               4025888
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
S1A S -0.30698(7) -0.04830(12) 0.00373(3) 0.0471(2) Uani 0.90 1 d P A 1
S1B S -0.1685(4) -0.4979(7) -0.0034(3) 0.045 Uiso 0.10 1 d PD A 2
N1 N 0.34213(16) 0.1079(3) 0.19981(7) 0.0321(4) Uani 1 1 d . . .
N2 N 0.35396(17) -0.1225(3) 0.20664(8) 0.0393(4) Uani 1 1 d . . .
N3 N 0.25018(17) -0.2171(3) 0.17062(8) 0.0396(4) Uani 1 1 d . . .
C1 C 0.17199(19) -0.0453(3) 0.14061(9) 0.0328(4) Uani 1 1 d . . .
C2 C 0.23082(19) 0.1632(3) 0.15931(9) 0.0333(4) Uani 1 1 d . . .
H2 H 0.1996 0.3132 0.1464 0.040 Uiso 1 1 calc R . .
C3 C 0.45057(19) 0.2596(4) 0.23155(9) 0.0355(4) Uani 1 1 d . . .
H3A H 0.4847 0.1961 0.2712 0.043 Uiso 1 1 calc R . .
H3B H 0.4115 0.4144 0.2360 0.043 Uiso 1 1 calc R . .
C4 C 0.0507(2) -0.0974(4) 0.09807(9) 0.0366(5) Uani 1 1 d . . .
C5 C -0.0488(2) -0.1538(4) 0.06327(9) 0.0380(5) Uani 1 1 d . A .
C11 C 0.56931(18) 0.2827(3) 0.20005(8) 0.0304(4) Uani 1 1 d . . .
C12 C 0.6642(2) 0.1058(3) 0.20168(9) 0.0344(4) Uani 1 1 d . . .
H12 H 0.6548 -0.0316 0.2228 0.041 Uiso 1 1 calc R . .
C13 C 0.7726(2) 0.1278(4) 0.17272(9) 0.0387(5) Uani 1 1 d . . .
H13 H 0.8369 0.0055 0.1740 0.046 Uiso 1 1 calc R . .
C14 C 0.7874(2) 0.3279(4) 0.14181(9) 0.0396(5) Uani 1 1 d . . .
H14 H 0.8616 0.3432 0.1219 0.047 Uiso 1 1 calc R . .
C15 C 0.6934(2) 0.5051(4) 0.14026(9) 0.0399(5) Uani 1 1 d . . .
H15 H 0.7029 0.6422 0.1190 0.048 Uiso 1 1 calc R . .
C16 C 0.5855(2) 0.4838(3) 0.16948(9) 0.0357(4) Uani 1 1 d . . .
H16 H 0.5222 0.6074 0.1686 0.043 Uiso 1 1 calc R . .
C21 C -0.1680(2) -0.2237(4) 0.02278(8) 0.0358(4) Uani 1 1 d D . .
C22A C -0.1913(2) -0.4392(3) -0.00572(11) 0.0258(4) Uani 0.90 1 d P A 1
H22A H -0.1266 -0.5620 -0.0018 0.031 Uiso 0.90 1 calc PR A 1
C22B C -0.2942(10) -0.1173(14) -0.0014(9) 0.030 Uiso 0.10 1 d PD A 2
H22B H -0.3111 0.0387 0.0077 0.036 Uiso 0.10 1 calc PR A 2
C23 C -0.3275(2) -0.4466(4) -0.04181(9) 0.0438(5) Uani 1 1 d D . .
H23 H -0.3638 -0.5774 -0.0643 0.053 Uiso 1 1 calc R A 1
C24 C -0.3971(2) -0.2490(4) -0.04015(10) 0.0476(6) Uani 1 1 d D A .
H24 H -0.4878 -0.2247 -0.0615 0.057 Uiso 1 1 calc R B 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'
S S 0.1246 0.1234 '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
C24 S1A C21 93.03(11) . . ?
C23 S1B C21 87.79(14) . . ?
C2 N1 N2 111.08(16) . . ?
C2 N1 C3 129.10(17) . . ?
N2 N1 C3 119.62(16) . . ?
N3 N2 N1 107.38(16) . . ?
N2 N3 C1 108.56(16) . . ?
N3 C1 C2 108.32(17) . . ?
N3 C1 C4 121.05(18) . . ?
C2 C1 C4 130.63(19) . . ?
N1 C2 C1 104.66(17) . . ?
N1 C3 C11 111.89(15) . . ?
C5 C4 C1 176.3(2) . . ?
C4 C5 C21 178.8(2) . . ?
C12 C11 C16 119.00(18) . . ?
C12 C11 C3 120.81(18) . . ?
C16 C11 C3 120.19(18) . . ?
C13 C12 C11 120.56(19) . . ?
C12 C13 C14 120.16(19) . . ?
C15 C14 C13 119.47(19) . . ?
C14 C15 C16 120.41(19) . . ?
C15 C16 C11 120.39(19) . . ?
C22A C21 C5 127.03(18) . . ?
C22B C21 C5 134.4(2) . . ?
C22B C21 S1B 109.0(2) . . ?
C5 C21 S1B 116.57(17) . . ?
C22A C21 S1A 110.89(15) . . ?
C5 C21 S1A 122.07(16) . . ?
C21 C22A C23 110.32(17) . . ?
C21 C22B C24 118.9(2) . . ?
C24 C23 C22A 112.7(2) . . ?
C24 C23 S1B 124.82(19) . . ?
C23 C24 C22B 99.4(2) . . ?
C23 C24 S1A 113.02(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
S1A C24 1.683(2) . ?
S1A C21 1.700(2) . ?
S1B C23 1.6798(3) . ?
S1B C21 1.6998(3) . ?
N1 C2 1.342(2) . ?
N1 N2 1.346(2) . ?
N1 C3 1.470(2) . ?
N2 N3 1.313(2) . ?
N3 C1 1.366(3) . ?
C1 C2 1.373(3) . ?
C1 C4 1.432(3) . ?
C3 C11 1.513(3) . ?
C4 C5 1.193(3) . ?
C5 C21 1.419(3) . ?
C11 C12 1.387(3) . ?
C11 C16 1.390(3) . ?
C12 C13 1.385(3) . ?
C13 C14 1.387(3) . ?
C14 C15 1.383(3) . ?
C15 C16 1.384(3) . ?
C21 C22A 1.410(3) . ?
C21 C22B 1.4100(3) . ?
C22A C23 1.445(3) . ?
C22B C24 1.4400(3) . ?
C23 C24 1.341(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 -0.1(2) . . . . ?
C3 N1 N2 N3 -175.36(16) . . . . ?
N1 N2 N3 C1 0.1(2) . . . . ?
N2 N3 C1 C2 -0.1(2) . . . . ?
N2 N3 C1 C4 -179.76(17) . . . . ?
N2 N1 C2 C1 0.0(2) . . . . ?
C3 N1 C2 C1 174.74(17) . . . . ?
N3 C1 C2 N1 0.0(2) . . . . ?
C4 C1 C2 N1 179.68(19) . . . . ?
C2 N1 C3 C11 -91.3(2) . . . . ?
N2 N1 C3 C11 83.1(2) . . . . ?
N3 C1 C4 C5 -1(3) . . . . ?
C2 C1 C4 C5 179(100) . . . . ?
C1 C4 C5 C21 53(14) . . . . ?
N1 C3 C11 C12 -76.1(2) . . . . ?
N1 C3 C11 C16 104.6(2) . . . . ?
C16 C11 C12 C13 -0.8(3) . . . . ?
C3 C11 C12 C13 179.93(17) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C12 C13 C14 C15 0.1(3) . . . . ?
C13 C14 C15 C16 0.3(3) . . . . ?
C14 C15 C16 C11 -0.9(3) . . . . ?
C12 C11 C16 C15 1.2(3) . . . . ?
C3 C11 C16 C15 -179.54(18) . . . . ?
C4 C5 C21 C22A -76(12) . . . . ?
C4 C5 C21 C22B 103(12) . . . . ?
C4 C5 C21 S1B -75(12) . . . . ?
C4 C5 C21 S1A 102(12) . . . . ?
C23 S1B C21 C22B 0.0(12) . . . . ?
C23 S1B C21 C5 178.7(2) . . . . ?
C24 S1A C21 C22A 0.65(19) . . . . ?
C24 S1A C21 C5 -178.04(18) . . . . ?
C5 C21 C22A C23 177.7(2) . . . . ?
S1A C21 C22A C23 -0.9(3) . . . . ?
C5 C21 C22B C24 -176.8(7) . . . . ?
S1B C21 C22B C24 2(2) . . . . ?
C21 C22A C23 C24 0.8(3) . . . . ?
C21 S1B C23 C24 -1.9(6) . . . . ?
S1B C23 C24 C22B 2.7(11) . . . . ?
C22A C23 C24 S1A -0.4(3) . . . . ?
C21 C22B C24 C23 -2.5(19) . . . . ?
C21 S1A C24 C23 -0.16(19) . . . . ?
