#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/56/2005688.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_2005688
loop_
_publ_author_name
'Zhang, Z.-Y.'
'Zou, N.'
'Zhu, Y.'
'Zhao, L.'
'Li, M.'
_publ_section_title
;Studies on Condensed Heterocyclic Compounds. XIII.
 6-(4-Methylphenyl)-3-(1-naphthylmethylene)-s-triazolo[3,4-b][1,3,4]thiadiazole
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2787
_journal_page_last               2789
_journal_paper_doi               10.1107/S0108270196001746
_journal_volume                  52
_journal_year                    1996
_chemical_formula_moiety         'C21 H16 N4 S'
_chemical_formula_sum            'C21 H16 N4 S'
_chemical_formula_weight         356
_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_type_scat_source           'SDP/PDP (Enraf-Nonius, 1985)'
_cell_angle_alpha                90.29(1)
_cell_angle_beta                 109.01(1)
_cell_angle_gamma                104.1(1)
_cell_formula_units_Z            2
_cell_length_a                   9.430(1)
_cell_length_b                   10.007(1)
_cell_length_c                   10.023(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      35
_cell_measurement_theta_min      15
_cell_volume                     863.6(5)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1985)'
_computing_data_reduction        'SDP/PDP (Enraf-Nonius, 1985)'
_computing_molecular_graphics    'ORTEP Johnson (1976)'
_computing_publication_material  ' '
_computing_structure_refinement  SDP/PDP
_computing_structure_solution    SDP/PDP
_diffrn_measurement_device       'Enraf-Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.016
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3131
_diffrn_reflns_theta_max         60
_diffrn_standards_decay_%        none
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.706
_exptl_absorpt_correction_T_max  0.9988
_exptl_absorpt_correction_T_min  0.5795
_exptl_absorpt_correction_type   'empirical (\y scan; SDP)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_description       prism
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.670
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   0.91
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_parameters     299
_refine_ls_number_reflns         2559
_refine_ls_R_factor_obs          0.069
_refine_ls_shift/esd_max         0.5
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      unit
_refine_ls_wR_factor_obs         0.072
_reflns_number_observed          2559
_reflns_number_total             2753
_reflns_observed_criterion       I>=3\s(I)
_cod_data_source_file            ta1008.cif
_cod_data_source_block           ta1008a
_cod_original_cell_volume        863.6
_cod_database_code               2005688
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_B_iso_or_equiv
S .6115(1) .49991(9) .3069(1) 3.59(2)
N1 .5179(3) .2522(3) .1722(3) 3.06(6)
N2 .4680(3) .2482(3) .2872(3) 2.91(6)
N3 .3760(4) .2047(3) .4590(3) 3.79(7)
N4 .4535(4) .3461(3) .4774(3) 3.88(7)
C1 .8796(5) .5466(5) -.2532(5) 5.3(1)
C2 .8067(4) .5017(4) -.1422(4) 3.80(9)
C3 .7181(5) .3680(4) -.1477(4) 4.4(1)
C4 .6481(5) .3268(4) -.0476(4) 3.91(9)
C5 .6664(4) .4216(4) .0633(4) 3.10(8)
C6 .7526(5) .5554(4) .0680(4) 4.2(1)
C7 .8216(5) .5955(4) -.0329(4) 4.4(1)
C8 .5959(4) .3776(4) .1714(4) 2.99(8)
C9 .5056(4) .3678(4) .3719(4) 3.23(8)
C10 .3871(4) .1478(4) .3451(4) 3.20(8)
C11 .3266(4) -.0018(4) .2906(4) 3.80(9)
C12 .1928(4) -.0738(4) .3377(4) 3.34(8)
C13 .2165(5) -.1661(4) .4398(4) 4.0(1)
C14 .0961(5) -.2314(4) .4901(4) 4.4(1)
C15 -.0449(5) -.2056(4) .4413(4) 3.95(9)
C16 -.0742(4) -.1137(4) .3344(4) 3.38(8)
C17 -.2225(5) -.0866(5) .2802(5) 4.5(1)
C18 -.2501(5) .0037(5) .1770(5) 5.2(1)
C19 -.1317(6) .0698(5) .1273(5) 4.9(1)
C20 .0130(5) .0461(4) .1770(4) 4.1(1)
C21 .0459(4) -.0471(4) .2836(4) 3.10(8)
H1 1.013(5) .604(5) -.202(5) 4.0
H1' .936(5) .495(5) -.261(5) 4.0
H1" .788(5) .517(5) -.359(5) 4.0
H3 .684(5) .304(5) -.233(5) 4.0
H4 .538(5) .228(5) -.088(5) 4.0
H6 .794(5) .616(5) .155(5) 4.0
H7 .905(5) .686(5) -.010(5) 4.0
H11' .427(5) -.036(5) .334(5) 4.0
H11 .284(5) .001(5) .176(5) 4.0
H13 .327(5) -.164(5) .488(5) 4.0
H14 .133(5) -.291(5) .584(5) 4.0
H15 -.137(5) -.259(5) .469(5) 4.0
H17 -.321(5) -.140(5) .300(5) 4.0
H18 -.349(5) -.005(5) .143(5) 4.0
H19 -.157(5) .127(5) .041(5) 4.0
H20 .116(5) .098(5) .151(5) 4.0
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C8 S C9 87.7(2) yes
N2 N1 C8 107.6(3) yes
N1 N2 C9 118.5(3) yes
N1 N2 C10 135.2(3) yes
C9 N2 C10 106.5(3) yes
N4 N3 C10 108.9(3) yes
N3 N4 C9 105.6(3) yes
C1 C2 C3 121.7(4) yes
C1 C2 C7 120.6(4) yes
C3 C2 C7 117.6(4) yes
C2 C3 C4 122.1(5) yes
C3 C4 C5 119.9(3) yes
C4 C5 C6 118.3(4) yes
C4 C5 C8 120.0(3) yes
C6 C5 C8 121.7(4) yes
C5 C6 C7 121.3(4) yes
C2 C7 C6 120.9(4) yes
S C8 N1 116.9(4) yes
S C8 C5 119.9(2) yes
N1 C8 C5 123.2(3) yes
S C9 N2 109.3(3) yes
S C9 N4 139.8(3) yes
N2 C9 N4 110.0(3) yes
N2 C10 N3 108.2(4) yes
N2 C10 C11 125.4(4) yes
N3 C10 C11 126.4(4) yes
C10 C11 C12 112.0(4) yes
C11 C12 C13 119.1(4) yes
C11 C12 C21 122.0(3) yes
C13 C12 C21 118.9(4) yes
C12 C13 C14 120.7(4) yes
C13 C14 C15 121.5(5) yes
C14 C15 C16 119.4(4) yes
C15 C16 C17 120.3(4) yes
C15 C16 C21 119.6(4) yes
C17 C16 C21 120.1(4) yes
C16 C17 C18 120.1(4) yes
C17 C18 C19 119.9(4) yes
C18 C19 C20 121.6(4) yes
C19 C20 C21 120.1(4) yes
C12 C21 C16 119.9(3) yes
C12 C21 C20 121.9(4) yes
C16 C21 C20 118.2(4) yes
H1 C1 H1' 69(4) no
H1 C1 H1" 140(4) no
H1' C1 H1" 99(4) no
H11' C11 H11 117(4) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S C8 1.769(4) yes
S C9 1.720(4) yes
N1 N2 1.377(5) yes
N1 C8 1.292(4) yes
N2 C9 1.365(5) yes
N2 C10 1.361(5) yes
N3 N4 1.406(4) yes
N3 C10 1.318(6) yes
N4 C9 1.302(6) yes
C1 C2 1.506(7) yes
C2 C3 1.384(6) yes
C2 C7 1.387(6) yes
C3 C4 1.384(7) yes
C4 C5 1.397(6) yes
C5 C6 1.379(5) yes
C5 C8 1.463(6) yes
C6 C7 1.382(7) yes
C10 C11 1.495(5) yes
C11 C12 1.510(6) yes
C12 C13 1.383(6) yes
C12 C21 1.406(5) yes
C13 C14 1.408(7) yes
C14 C15 1.349(7) yes
C15 C16 1.419(6) yes
C16 C17 1.419(6) yes
C16 C21 1.413(6) yes
C17 C18 1.380(7) yes
C18 C19 1.391(7) yes
C19 C20 1.372(7) yes
C20 C21 1.430(6) yes
C1 H1 1.19(4) no
C1 H1' .84(6) no
C1 H1" 1.11(4) no
C3 H3 .98(5) no
C4 H4 1.20(4) no
C6 H6 .97(5) no
C7 H7 1.01(4) no
C11 H11' 1.04(5) no
C11 H11 1.10(5) no
C13 H13 .99(5) no
C14 H14 1.11(5) no
C15 H15 1.03(5) no
C17 H17 1.03(5) no
C18 H18 .87(5) no
C19 H19 1.0(5) no
C20 H20 1.09(5) no
