#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/86/2008609.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_2008609
loop_
_publ_author_name
'Puviarasan, K.'
'Govindasamy, L.'
'Shanmuga Sundara Raj, S.'
'Velmurugan, D.'
'Jayanthi, G.'
'Hoong-Kun Fun'
_publ_section_title
;
 7-Methyl-3-(2-methylphenyl)-1,2,4-triazolo[3,4-b][1,3]benzothiazole,
 (I), and
 7-methyl-3-(4-methylphenyl)-1,2,4-triazolo[3,4-b][1,3]benzothiazole,
 (II)
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              948
_journal_page_last               951
_journal_paper_doi               10.1107/S0108270199000864
_journal_volume                  55
_journal_year                    1999
_chemical_formula_sum            'C16 H13 N3 S'
_chemical_formula_weight         279.35
_chemical_name_systematic
;
7-methyl-3-(4-methylphenyl)-1,2,4-triazolo-[3,4-b][1,3]benzothiazole
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   24.4820(12)
_cell_length_b                   7.5509(4)
_cell_length_c                   7.5060(4)
_cell_measurement_reflns_used    5360
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      33.20
_cell_measurement_theta_min      1.35
_cell_volume                     1387.57(12)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and PARST (Nardelli, 1995)'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_diffrn_measurement_method       ω-scan
_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  0.048
_diffrn_reflns_av_sigmaI/netI    0.054
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8674
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.70
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_correction_T_min  0.882
_exptl_absorpt_correction_type   'empirical (SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular block'
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.329
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3057
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.064
_refine_ls_R_factor_gt           0.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0727P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.125
_reflns_number_gt                2435
_reflns_number_total             3057
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            os1049.cif
_cod_data_source_block           vpv3m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               2008609
_cod_database_fobs_code          2008609
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
S1 .71136(3) .17046(9) .97245(10) .0603(2) Uani d . 1 . . S
N1 .80021(8) .3405(3) 1.0532(3) .0429(4) Uani d . 1 . . N
N2 .82072(11) .0607(3) .9885(4) .0684(7) Uani d . 1 . . N
N3 .86834(10) .1518(3) 1.0329(4) .0676(7) Uani d . 1 . . N
C1 .70750(10) .3926(3) 1.0398(3) .0459(6) Uani d . 1 . . C
C2 .66008(11) .4957(4) 1.0511(4) .0533(6) Uani d . 1 . . C
C3 .66327(10) .6689(4) 1.1086(4) .0496(6) Uani d . 1 . . C
C4 .71385(9) .7348(4) 1.1616(4) .0463(6) Uani d . 1 . . C
C5 .76133(10) .6354(3) 1.1505(3) .0416(5) Uani d . 1 . . C
C6 .75811(9) .4665(3) 1.0843(3) .0396(5) Uani d . 1 . . C
C7 .78165(11) .1768(3) 1.0029(4) .0523(7) Uani d . 1 . . C
C8 .85582(11) .3182(3) 1.0701(4) .0506(6) Uani d . 1 . . C
C9 .89671(9) .4524(3) 1.1137(4) .0464(6) Uani d . 1 . . C
C10 .94337(12) .4041(4) 1.2105(4) .0587(7) Uani d . 1 . . C
C11 .98314(12) .5279(4) 1.2464(5) .0642(8) Uani d . 1 . . C
C12 .97829(12) .7013(4) 1.1904(5) .0627(8) Uani d . 1 . . C
C13 .93227(10) .7491(4) 1.0943(4) .0541(6) Uani d . 1 . . C
C14 .89226(10) .6254(3) 1.0547(4) .0472(6) Uani d . 1 . . C
C15 .61374(12) .7878(5) 1.1106(5) .0702(9) Uani d . 1 . . C
H15A .5815 .7176 1.1287 .105 Uiso calc R 1 . . H
H15B .6110 .8490 .9988 .105 Uiso calc R 1 . . H
H15C .6171 .8723 1.2054 .105 Uiso calc R 1 . . H
C16 1.02166(15) .8382(5) 1.2315(8) .1003(14) Uani d . 1 . . C
H16A 1.0492 .7864 1.3061 .150 Uiso calc R 1 . . H
H16B 1.0053 .9368 1.2920 .150 Uiso calc R 1 . . H
H16C 1.0380 .8782 1.1224 .150 Uiso calc R 1 . . H
H2 .6263(12) .448(4) 1.015(4) .057(8) Uiso d . 1 . . H
H4 .7149(10) .848(4) 1.205(4) .052(9) Uiso d . 1 . . H
H5 .7954(11) .685(4) 1.183(4) .050(8) Uiso d . 1 . . H
H11 1.0125(17) .497(4) 1.322(5) .086(11) Uiso d . 1 . . H
H10 .9443(13) .292(4) 1.256(5) .066(9) Uiso d . 1 . . H
H13 .9293(9) .856(3) 1.048(3) .036(6) Uiso d . 1 . . H
H14 .8626(12) .660(3) .975(5) .058(8) Uiso d . 1 . . H
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_publ_flag
C7 S1 C1 89.38(12) y
C7 N1 C8 104.0(2) ?
C7 N1 C6 114.1(2) ?
C8 N1 C6 141.6(2) y
C7 N2 N3 105.2(2) ?
C8 N3 N2 109.0(2) ?
C6 C1 C2 119.9(2) ?
C6 C1 S1 113.7(2) ?
C2 C1 S1 126.4(2) ?
C3 C2 C1 119.9(2) ?
C2 C3 C4 118.6(2) ?
C2 C3 C15 121.4(3) ?
C4 C3 C15 120.0(3) ?
C5 C4 C3 122.4(3) ?
C6 C5 C4 118.5(2) ?
C5 C6 C1 120.6(2) ?
C5 C6 N1 129.8(2) ?
C1 C6 N1 109.6(2) ?
N2 C7 N1 112.7(2) ?
N2 C7 S1 134.3(2) y
N1 C7 S1 112.93(19) ?
N3 C8 N1 109.0(2) ?
N3 C8 C9 123.2(2) ?
N1 C8 C9 127.8(2) ?
C14 C9 C10 118.4(2) ?
C14 C9 C8 121.9(2) ?
C10 C9 C8 119.6(2) ?
C11 C10 C9 120.1(3) ?
C10 C11 C12 121.6(3) ?
C11 C12 C13 118.4(3) ?
C11 C12 C16 121.7(3) ?
C13 C12 C16 119.9(3) ?
C14 C13 C12 120.7(3) ?
C9 C14 C13 120.8(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C7 . 1.736(3) y
S1 C1 . 1.754(3) y
N1 C7 . 1.370(3) y
N1 C8 . 1.378(3) y
N1 C6 . 1.422(3) y
N2 C7 . 1.302(3) y
N2 N3 . 1.394(3) y
N3 C8 . 1.323(3) y
C1 C6 . 1.399(3) ?
C1 C2 . 1.400(4) ?
C2 C3 . 1.380(4) ?
C3 C4 . 1.392(4) ?
C3 C15 . 1.509(4) y
C4 C5 . 1.386(3) ?
C5 C6 . 1.371(3) ?
C8 C9 . 1.462(4) ?
C9 C14 . 1.384(4) ?
C9 C10 . 1.402(4) ?
C10 C11 . 1.376(5) ?
C11 C12 . 1.381(4) ?
C12 C13 . 1.386(4) ?
C12 C16 . 1.513(4) y
C13 C14 . 1.386(4) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C4 H4 N2 4_665 0.91(3) 2.81(3) 3.577(4) 143(2) yes
C13 H13 N3 1_565 0.88(3) 2.69(3) 3.451(4) 145(3) yes
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_publ_flag
C7 N2 N3 C8 -0.6(4) y
C7 S1 C1 C6 -0.4(2) y
C7 S1 C1 C2 179.5(2) ?
C6 C1 C2 C3 -1.0(4) ?
S1 C1 C2 C3 179.2(2) ?
C1 C2 C3 C4 -2.7(4) ?
C1 C2 C3 C15 175.8(3) ?
C2 C3 C4 C5 3.2(4) ?
C15 C3 C4 C5 -175.4(3) ?
C3 C4 C5 C6 0.2(4) ?
C4 C5 C6 C1 -4.0(4) ?
C4 C5 C6 N1 177.5(2) ?
C2 C1 C6 C5 4.4(4) ?
S1 C1 C6 C5 -175.70(19) ?
C2 C1 C6 N1 -176.8(2) ?
S1 C1 C6 N1 3.1(3) y
C7 N1 C6 C5 173.5(3) ?
C8 N1 C6 C5 1.2(5) ?
C7 N1 C6 C1 -5.1(3) y
C8 N1 C6 C1 -177.4(3) ?
N3 N2 C7 N1 0.4(4) y
N3 N2 C7 S1 -179.7(3) ?
C8 N1 C7 N2 0.0(3) y
C6 N1 C7 N2 -175.1(2) ?
C8 N1 C7 S1 -179.98(19) ?
C6 N1 C7 S1 5.0(3) y
C1 S1 C7 N2 177.5(3) ?
C1 S1 C7 N1 -2.6(2) y
N2 N3 C8 N1 0.6(3) y
N2 N3 C8 C9 -177.0(3) ?
C7 N1 C8 N3 -0.4(3) y
C6 N1 C8 N3 172.4(3) ?
C7 N1 C8 C9 177.1(3) ?
C6 N1 C8 C9 -10.1(5) ?
N3 C8 C9 C14 141.7(3) ?
N1 C8 C9 C14 -35.4(4) ?
N3 C8 C9 C10 -34.9(4) ?
N1 C8 C9 C10 147.9(3) ?
C14 C9 C10 C11 0.7(4) ?
C8 C9 C10 C11 177.5(3) ?
C9 C10 C11 C12 0.5(5) ?
C10 C11 C12 C13 -0.7(5) ?
C10 C11 C12 C16 179.3(4) ?
C11 C12 C13 C14 -0.3(5) ?
C16 C12 C13 C14 179.7(4) ?
C10 C9 C14 C13 -1.7(4) ?
C8 C9 C14 C13 -178.4(3) ?
C12 C13 C14 C9 1.5(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8716040
