#------------------------------------------------------------------------------
#$Date: 2011-09-17 23:27:16 +0300 (Sat, 17 Sep 2011) $
#$Revision: 26029 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2212422.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_2212422
loop_
_publ_author_name
'Sefero\(glu, Zeynel'
'H\"okelek, Tuncer'
'\,Sahin, Ertan'
'Ertan, Nermin'
_publ_section_title
;
1-Methyl-2-phenyl-3-(5-ethyl-1,3,4-thiadiazol-2-yldiazenyl)-1<i>H</i>-indole
;
_journal_coeditor_code           XU2194
_journal_issue                   2
_journal_name_full               'Acta Crystallographica, Section E'
_journal_page_first              o568
_journal_page_last               o570
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C19 H17 N5 S'
_chemical_formula_moiety         'C19 H17 N5 S'
_chemical_formula_sum            'C19 H17 N5 S'
_chemical_formula_weight         347.45
_chemical_melting_point          494.0(10)
_chemical_name_systematic
;
1-Methyl-2-phenyl-3-(5-ethyl-1,3,4-thiadiazol-2-yldiazenyl)-1H-indole
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.664(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.7629(14)
_cell_length_b                   10.0115(8)
_cell_length_c                   16.568(2)
_cell_measurement_reflns_used    5884
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      30.8
_cell_measurement_theta_min      2.1
_cell_volume                     1759.9(3)
_computing_cell_refinement       CrystalClear
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.98
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID-S'
_diffrn_measurement_method       \w
_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  0.030
_diffrn_reflns_av_sigmaI/netI    0.110
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            51782
_diffrn_reflns_theta_full        30.8
_diffrn_reflns_theta_max         30.8
_diffrn_reflns_theta_min         2.4
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.22
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         5423
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.231
_refine_ls_R_factor_gt           0.102
_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/[\s^2^(Fo^2^)+(0.0463P)^2^+0.8413P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.169
_refine_ls_wR_factor_ref         0.212
_reflns_number_gt                2212
_reflns_number_total             5423
_reflns_threshold_expression     I>2\s(I)
_[local]_cod_data_source_file    xu2194.cif
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '493-495 K' was changed to
'494.0(10)' - the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               2212422
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_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
S S1 0.67051(10) 0.07616(12) 0.52261(6) 0.0747(4) Uani d . 1
N N1 0.9996(3) -0.3382(3) 0.38483(18) 0.0588(8) Uani d . 1
N N2 0.8562(3) -0.1080(3) 0.50076(18) 0.0610(8) Uani d . 1
N N3 0.8877(3) -0.0666(3) 0.57562(19) 0.0643(9) Uani d . 1
N N4 0.8114(3) 0.0853(3) 0.66375(19) 0.0739(10) Uani d . 1
N N5 0.7120(4) 0.1724(4) 0.6672(2) 0.0790(11) Uani d . 1
C C1 0.8009(4) 0.0272(4) 0.5927(2) 0.0592(10) Uani d . 1
C C2 0.6333(4) 0.1766(4) 0.5993(3) 0.0729(12) Uani d . 1
C C3 0.9330(3) -0.2012(4) 0.4755(2) 0.0569(9) Uani d . 1
C C4 0.9114(3) -0.2449(4) 0.3934(2) 0.0580(10) Uani d . 1
C C5 1.0797(4) -0.3574(4) 0.4603(2) 0.0573(9) Uani d . 1
C C6 1.1799(4) -0.4430(4) 0.4796(2) 0.0704(11) Uani d . 1
C C7 1.2427(4) -0.4423(5) 0.5594(3) 0.0756(12) Uani d . 1
C C8 1.2061(4) -0.3589(4) 0.6186(3) 0.0729(12) Uani d . 1
C C9 1.1054(4) -0.2742(4) 0.5988(3) 0.0656(11) Uani d . 1
C C10 1.0406(3) -0.2727(4) 0.5184(2) 0.0570(9) Uani d . 1
C C11 0.8095(4) -0.2023(4) 0.3279(2) 0.0615(10) Uani d . 1
C C12 0.7390(4) -0.2943(5) 0.2767(3) 0.0744(12) Uani d . 1
C C13 0.6370(5) -0.2541(6) 0.2199(3) 0.0916(15) Uani d . 1
C C14 0.6064(6) -0.1217(7) 0.2124(4) 0.105(2) Uani d . 1
C C15 0.6770(5) -0.0281(6) 0.2619(3) 0.0935(16) Uani d . 1
C C16 0.7784(5) -0.0684(5) 0.3192(3) 0.0750(12) Uani d . 1
C C17 1.0232(4) -0.3990(4) 0.3081(2) 0.0779(12) Uani d . 1
C C18 0.5150(5) 0.2585(6) 0.5878(3) 0.125(2) Uani d . 1
C C19 0.4539(5) 0.2841(6) 0.5064(3) 0.122(2) Uani d . 1
H H6 1.2046 -0.4991 0.4405 0.084 Uiso calc R 1
H H17A 1.0013 -0.4920 0.3075 0.117 Uiso calc R 1
H H17B 1.1108 -0.3900 0.3042 0.117 Uiso calc R 1
H H17C 0.9729 -0.3549 0.2625 0.117 Uiso calc R 1
H H18A 0.4551 0.2139 0.6164 0.150 Uiso calc R 1
H H18B 0.5349 0.3438 0.6146 0.150 Uiso calc R 1
H H19A 0.4984 0.3530 0.4828 0.183 Uiso calc R 1
H H19B 0.3689 0.3125 0.5070 0.183 Uiso calc R 1
H H19C 0.4531 0.2041 0.4744 0.183 Uiso calc R 1
H H71 1.316(4) -0.501(4) 0.577(2) 0.087(14) Uiso d . 1
H H81 1.258(4) -0.364(4) 0.676(2) 0.076(12) Uiso d . 1
H H91 1.085(4) -0.224(4) 0.637(2) 0.076(13) Uiso d . 1
H H121 0.753(4) -0.381(4) 0.284(2) 0.069(13) Uiso d . 1
H H131 0.590(4) -0.331(5) 0.184(3) 0.104(16) Uiso d . 1
H H141 0.544(5) -0.091(6) 0.177(3) 0.14(2) Uiso d . 1
H H151 0.656(4) 0.073(5) 0.255(3) 0.105(16) Uiso d . 1
H H161 0.834(4) -0.003(4) 0.353(2) 0.090(15) Uiso d . 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.0724(7) 0.0875(8) 0.0612(6) 0.0229(6) 0.0022(5) -0.0144(6)
N1 0.062(2) 0.060(2) 0.0552(18) 0.0054(16) 0.0114(15) -0.0070(15)
N2 0.067(2) 0.059(2) 0.0571(19) 0.0041(16) 0.0107(15) 0.0001(16)
N3 0.071(2) 0.062(2) 0.0599(19) 0.0136(17) 0.0105(16) -0.0015(17)
N4 0.088(3) 0.073(2) 0.057(2) 0.018(2) 0.0008(17) -0.0076(18)
N5 0.090(3) 0.085(3) 0.062(2) 0.026(2) 0.0088(19) -0.0096(19)
C1 0.064(2) 0.058(2) 0.054(2) 0.0055(19) 0.0052(18) 0.0012(19)
C2 0.080(3) 0.079(3) 0.059(2) 0.024(2) 0.010(2) -0.013(2)
C3 0.060(2) 0.054(2) 0.057(2) 0.0076(19) 0.0117(18) 0.0003(18)
C4 0.059(2) 0.056(2) 0.059(2) -0.0003(19) 0.0090(18) 0.0012(19)
C5 0.059(2) 0.057(2) 0.055(2) 0.0047(19) 0.0097(18) 0.0041(18)
C6 0.075(3) 0.068(3) 0.067(3) 0.013(2) 0.010(2) -0.007(2)
C7 0.074(3) 0.076(3) 0.075(3) 0.016(3) 0.009(2) 0.007(2)
C8 0.079(3) 0.073(3) 0.062(3) 0.010(2) 0.000(2) 0.003(2)
C9 0.077(3) 0.067(3) 0.053(2) 0.005(2) 0.011(2) 0.002(2)
C10 0.059(2) 0.055(2) 0.058(2) 0.0011(19) 0.0132(18) -0.0011(19)
C11 0.063(2) 0.067(3) 0.052(2) 0.002(2) 0.0034(18) 0.004(2)
C12 0.081(3) 0.074(3) 0.066(3) 0.005(3) 0.006(2) 0.005(3)
C13 0.091(4) 0.101(4) 0.074(3) -0.001(3) -0.014(3) 0.009(3)
C14 0.099(4) 0.117(5) 0.085(4) 0.013(4) -0.020(3) 0.023(4)
C15 0.103(4) 0.088(4) 0.086(4) 0.021(3) 0.004(3) 0.022(3)
C16 0.085(3) 0.068(3) 0.070(3) 0.004(3) 0.009(2) 0.012(2)
C17 0.085(3) 0.090(3) 0.059(2) 0.008(3) 0.015(2) -0.017(2)
C18 0.121(4) 0.167(6) 0.082(4) 0.085(4) 0.004(3) -0.018(4)
C19 0.114(5) 0.120(5) 0.120(5) 0.057(4) -0.014(4) -0.016(4)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1250 0.1230 '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
C2 S1 C1 86.2(2)
C4 N1 C5 109.6(3)
C4 N1 C17 127.0(3)
C5 N1 C17 122.8(3)
N3 N2 C3 116.1(3)
N2 N3 C1 109.5(3)
C1 N4 N5 111.5(3)
C2 N5 N4 112.5(3)
N4 C1 N3 121.8(3)
N4 C1 S1 114.7(3)
N3 C1 S1 123.5(3)
N5 C2 C18 123.2(4)
N5 C2 S1 115.2(3)
C18 C2 S1 121.6(3)
N2 C3 C4 120.0(3)
N2 C3 C10 131.9(3)
C4 C3 C10 108.0(3)
N1 C4 C3 108.1(3)
N1 C4 C11 124.8(3)
C3 C4 C11 127.1(4)
C6 C5 C10 122.2(4)
C6 C5 N1 129.3(4)
C10 C5 N1 108.5(3)
C5 C6 C7 117.4(4)
C5 C6 H6 121.3
C7 C6 H6 121.3
C6 C7 C8 121.7(4)
C6 C7 H71 121(2)
C8 C7 H71 117(2)
C9 C8 C7 120.5(4)
C9 C8 H81 123(2)
C7 C8 H81 117(2)
C8 C9 C10 118.9(4)
C8 C9 H91 118(3)
C10 C9 H91 123(3)
C9 C10 C5 119.3(4)
C9 C10 C3 134.9(4)
C5 C10 C3 105.7(3)
C16 C11 C12 118.8(4)
C16 C11 C4 119.7(4)
C12 C11 C4 121.5(4)
C13 C12 C11 120.9(5)
C13 C12 H121 118(3)
C11 C12 H121 120(3)
C14 C13 C12 119.8(6)
C14 C13 H131 125(3)
C12 C13 H131 116(3)
C13 C14 C15 120.2(5)
C13 C14 H141 123(4)
C15 C14 H141 117(4)
C16 C15 C14 120.0(5)
C16 C15 H151 120(3)
C14 C15 H151 120(3)
C15 C16 C11 120.3(5)
C15 C16 H161 122(2)
C11 C16 H161 118(2)
N1 C17 H17A 109.5
N1 C17 H17B 109.5
H17A C17 H17B 109.5
N1 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C19 C18 C2 117.8(4)
C19 C18 H18A 107.9
C2 C18 H18A 107.9
C19 C18 H18B 107.9
C2 C18 H18B 107.9
H18A C18 H18B 107.2
C18 C19 H19A 109.5
C18 C19 H19B 109.5
H19A C19 H19B 109.5
C18 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C1 1.735(4)
S1 C2 1.719(4)
N1 C4 1.356(4)
N1 C5 1.408(4)
N1 C17 1.470(4)
N3 N2 1.297(4)
N3 C1 1.387(4)
N2 C3 1.358(4)
N4 N5 1.390(4)
N4 C1 1.301(4)
N5 C2 1.290(5)
C2 C18 1.499(6)
C4 C3 1.410(5)
C4 C11 1.471(5)
C5 C6 1.372(5)
C6 H6 0.9300
C7 C6 1.380(5)
C7 H71 0.99(4)
C8 C7 1.394(6)
C8 C9 1.371(6)
C8 H81 1.02(4)
C9 H91 0.87(4)
C10 C3 1.444(5)
C10 C5 1.399(5)
C10 C9 1.396(5)
C11 C12 1.389(6)
C11 C16 1.383(6)
C12 C13 1.380(6)
C12 H121 0.88(4)
C14 H141 0.87(5)
C15 C14 1.386(8)
C15 H151 1.04(5)
C13 C14 1.366(7)
C13 H131 1.05(5)
C16 C15 1.381(6)
C16 H161 0.99(4)
C17 H17A 0.9600
C17 H17B 0.9600
C17 H17C 0.9600
C18 C19 1.422(6)
C18 H18A 0.9700
C18 H18B 0.9700
C19 H19A 0.9600
C19 H19B 0.9600
C19 H19C 0.9600
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
C2 S1 C1 N4 -1.3(3)
C2 S1 C1 N3 178.4(4)
C1 S1 C2 N5 0.9(4)
C1 S1 C2 C18 -176.9(5)
C5 N1 C4 C3 0.1(4)
C5 N1 C4 C11 -178.0(3)
C17 N1 C4 C3 -171.9(4)
C17 N1 C4 C11 10.0(6)
C4 N1 C5 C6 179.1(4)
C4 N1 C5 C10 -0.2(4)
C17 N1 C5 C6 -8.6(6)
C17 N1 C5 C10 172.2(3)
N3 N2 C3 C4 -175.5(3)
N3 N2 C3 C10 5.4(6)
C1 N3 N2 C3 -179.7(3)
N2 N3 C1 S1 0.9(5)
N2 N3 C1 N4 -179.4(4)
N5 N4 C1 N3 -178.4(3)
N5 N4 C1 S1 1.4(5)
C1 N4 N5 C2 -0.7(5)
N4 N5 C2 C18 177.4(5)
N4 N5 C2 S1 -0.3(5)
N5 C2 C18 C19 163.4(5)
S1 C2 C18 C19 -18.9(8)
N1 C4 C3 N2 -179.3(3)
C11 C4 C3 N2 -1.2(6)
N1 C4 C3 C10 0.1(4)
C11 C4 C3 C10 178.1(4)
N1 C4 C11 C12 44.7(6)
N1 C4 C11 C16 -138.7(4)
C3 C4 C11 C12 -133.1(4)
C3 C4 C11 C16 43.6(6)
C10 C5 C6 C7 -0.4(6)
N1 C5 C6 C7 -179.6(4)
C8 C7 C6 C5 0.3(7)
C7 C8 C9 C10 -0.3(7)
C9 C8 C7 C6 0.1(7)
C9 C10 C3 N2 -0.1(8)
C5 C10 C3 N2 179.0(4)
C9 C10 C3 C4 -179.3(4)
C5 C10 C3 C4 -0.2(4)
C9 C10 C5 C6 0.2(6)
C3 C10 C5 C6 -179.1(4)
C9 C10 C5 N1 179.5(3)
C3 C10 C5 N1 0.2(4)
C5 C10 C9 C8 0.2(6)
C3 C10 C9 C8 179.2(4)
C16 C11 C12 C13 -2.1(7)
C4 C11 C12 C13 174.6(4)
C12 C11 C16 C15 1.5(7)
C4 C11 C16 C15 -175.2(4)
C11 C12 C13 C14 1.6(8)
C11 C16 C15 C14 -0.4(8)
C12 C13 C14 C15 -0.4(9)
C16 C15 C14 C13 -0.2(9)