#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/19/2211982.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_2211982
loop_
_publ_author_name
'Seferoğlu, Zeynel'
'Hökelek, Tuncer'
'Şahin, Ertan'
'Ertan , Nermin'
_publ_section_title
;
 1-Methyl-2-phenyl-3-(1,3,4-thiadiazol-2-yldiazenyl)-1H-indole
;
_journal_coeditor_code           XU2181
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o148
_journal_page_last               o150
_journal_paper_doi               10.1107/S160053680605210X
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C17 H13 N5 S'
_chemical_formula_moiety         'C17 H13 N5 S'
_chemical_formula_sum            'C17 H13 N5 S'
_chemical_formula_weight         319.38
_chemical_melting_point          458.5(5)
_chemical_name_systematic
;
1-Methyl-2-phenyl-3-(thiadiazol-2-yldiazenyl)-1H-indole
;
_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                 104.4222(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.0288(2)
_cell_length_b                   17.3757(3)
_cell_length_c                   11.1899(3)
_cell_measurement_reflns_used    7865
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      30.5
_cell_measurement_theta_min      2.2
_cell_volume                     1511.86(6)
_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 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID-S'
_diffrn_measurement_method       ω
_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  0.058
_diffrn_reflns_av_sigmaI/netI    0.036
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            44017
_diffrn_reflns_theta_full        30.7
_diffrn_reflns_theta_max         30.7
_diffrn_reflns_theta_min         2.2
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_correction_T_min  0.937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.32
_refine_ls_extinction_coef       0.072(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         4636
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.075
_refine_ls_R_factor_gt           0.053
_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)+(0.0634P)²+0.1946P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.129
_refine_ls_wR_factor_ref         0.146
_reflns_number_gt                3243
_reflns_number_total             4636
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2181.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '458-459' was changed to '458.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value '458-459' was changed to '458.5(5)' -
the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2211982
_cod_database_fobs_code          2211982
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_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_occupancy
S S1 0.93379(6) 0.84130(3) 0.30097(4) 0.06030(17) Uani d 1
N N1 1.36363(18) 1.13728(8) 0.45217(13) 0.0539(3) Uani d 1
N N2 1.15927(16) 0.95625(7) 0.42387(12) 0.0488(3) Uani d 1
N N3 1.16554(18) 0.90206(8) 0.50322(13) 0.0539(3) Uani d 1
N N4 1.0484(2) 0.77921(9) 0.51275(15) 0.0741(5) Uani d 1
N N5 0.9337(3) 0.72707(10) 0.44322(18) 0.0783(5) Uani d 1
C C1 1.0609(2) 0.84120(9) 0.45043(15) 0.0526(4) Uani d 1
C C2 0.8666(3) 0.75235(11) 0.3341(2) 0.0654(5) Uani d 1
C C3 1.25267(19) 1.02035(9) 0.46672(14) 0.0474(3) Uani d 1
C C4 1.35691(19) 1.04035(9) 0.58715(14) 0.0495(3) Uani d 1
C C5 1.3948(2) 1.00621(12) 0.70391(16) 0.0588(4) Uani d 1
C C6 1.4909(3) 1.04732(14) 0.80262(19) 0.0707(5) Uani d 1
C C7 1.5517(3) 1.12075(14) 0.7882(2) 0.0736(5) Uani d 1
C C8 1.5205(2) 1.15518(12) 0.6738(2) 0.0656(5) Uani d 1
C C9 1.4224(2) 1.11385(10) 0.57446(16) 0.0542(4) Uani d 1
C C10 1.2589(2) 1.08230(9) 0.38653(15) 0.0493(3) Uani d 1
C C11 1.1691(2) 1.09045(9) 0.25617(15) 0.0508(4) Uani d 1
C C12 0.9945(2) 1.07352(11) 0.21927(17) 0.0588(4) Uani d 1
C C13 0.9077(3) 1.07847(12) 0.09629(18) 0.0662(5) Uani d 1
C C14 0.9936(3) 1.09900(11) 0.00871(18) 0.0668(5) Uani d 1
C C15 1.1658(3) 1.11659(11) 0.04380(18) 0.0670(5) Uani d 1
C C16 1.2536(3) 1.11259(11) 0.16715(17) 0.0600(4) Uani d 1
C C17 1.3990(3) 1.21343(12) 0.4109(2) 0.0737(5) Uani d 1
H H21 0.780(3) 0.7247(13) 0.270(2) 0.083(7) Uiso d 1
H H51 1.357(3) 0.9553(12) 0.7125(18) 0.069(6) Uiso d 1
H H61 1.516(3) 1.0225(13) 0.882(2) 0.083(7) Uiso d 1
H H71 1.620(3) 1.1513(13) 0.863(2) 0.092(7) Uiso d 1
H H81 1.560(3) 1.2087(15) 0.668(2) 0.093(7) Uiso d 1
H H121 0.937(3) 1.0555(12) 0.2809(18) 0.072(6) Uiso d 1
H H131 0.782(3) 1.0639(13) 0.070(2) 0.088(7) Uiso d 1
H H141 0.934(3) 1.1012(12) -0.075(2) 0.081(6) Uiso d 1
H H151 1.228(3) 1.1305(13) -0.019(2) 0.090(7) Uiso d 1
H H161 1.370(2) 1.1271(10) 0.1909(17) 0.055(5) Uiso d 1
H H171 1.383(4) 1.2519(18) 0.477(3) 0.122(10) Uiso d 1
H H172 1.321(4) 1.2289(16) 0.336(3) 0.111(9) Uiso d 1
H H173 1.522(3) 1.2153(14) 0.406(2) 0.103(8) Uiso d 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_publ_flag
C2 S1 C1 86.07(10) y
C10 N1 C9 109.74(14) y
C10 N1 C17 127.69(16) ?
C9 N1 C17 122.23(16) ?
N3 N2 C3 115.61(13) y
N2 N3 C1 110.39(14) y
C1 N4 N5 111.71(16) y
C2 N5 N4 111.95(16) y
N4 C1 N3 121.48(16) y
N4 C1 S1 114.45(14) y
N3 C1 S1 124.05(12) y
N5 C2 S1 115.81(16) y
N5 C2 H21 125.0(13) ?
S1 C2 H21 119.2(13) ?
N2 C3 C10 120.28(14) ?
N2 C3 C4 131.87(14) ?
C10 C3 C4 107.85(14) ?
C5 C4 C9 118.79(16) ?
C5 C4 C3 135.44(16) ?
C9 C4 C3 105.68(14) ?
C6 C5 C4 118.49(19) ?
C6 C5 H51 122.1(12) ?
C4 C5 H51 119.4(12) ?
C5 C6 C7 121.7(2) ?
C5 C6 H61 117.0(14) ?
C7 C6 H61 121.3(13) ?
C8 C7 C6 121.22(19) ?
C8 C7 H71 118.1(13) ?
C6 C7 H71 120.7(13) ?
C7 C8 C9 117.0(2) ?
C7 C8 H81 118.9(14) ?
C9 C8 H81 123.9(14) ?
C8 C9 N1 128.33(18) ?
C8 C9 C4 122.77(18) ?
N1 C9 C4 108.79(14) ?
N1 C10 C3 107.91(14) ?
N1 C10 C11 123.69(14) ?
C3 C10 C11 128.39(14) ?
C12 C11 C16 118.75(16) ?
C12 C11 C10 119.02(15) ?
C16 C11 C10 122.20(16) ?
C13 C12 C11 120.25(18) ?
C13 C12 H121 120.9(12) ?
C11 C12 H121 118.7(11) ?
C14 C13 C12 120.43(19) ?
C14 C13 H131 120.1(12) ?
C12 C13 H131 119.4(13) ?
C15 C14 C13 120.03(19) ?
C15 C14 H141 120.3(14) ?
C13 C14 H141 119.6(14) ?
C14 C15 C16 119.95(19) ?
C14 C15 H151 120.1(14) ?
C16 C15 H151 119.9(14) ?
C15 C16 C11 120.57(19) ?
C15 C16 H161 119.4(11) ?
C11 C16 H161 120.0(11) ?
N1 C17 H173 108.7(15) ?
N1 C17 H171 107.0(16) ?
H173 C17 H171 109(2) ?
N1 C17 H172 113.6(17) ?
H173 C17 H172 112(2) ?
H171 C17 H172 106(2) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S1 C2 1.708(2) y
S1 C1 1.7286(19) y
N1 C9 1.393(2) y
N1 C17 1.453(2) ?
N2 N3 1.2866(18) y
N2 C3 1.361(2) y
N3 C1 1.388(2) y
N4 N5 1.384(2) ?
N5 C2 1.284(3) y
C1 N4 1.300(2) y
C2 H21 0.99(2) ?
C3 C10 1.410(2) ?
C3 C4 1.441(2) ?
C4 C5 1.398(2) ?
C4 C9 1.402(2) ?
C5 C6 1.379(3) ?
C5 H51 0.95(2) ?
C6 H61 0.96(2) ?
C7 C8 1.378(3) ?
C7 C6 1.390(3) ?
C7 H71 1.03(3) ?
C8 H81 0.99(3) ?
C9 C8 1.392(3) ?
C10 N1 1.361(2) ?
C11 C12 1.391(3) ?
C11 C16 1.392(2) ?
C11 C10 1.464(2) ?
C12 C13 1.382(3) ?
C12 H121 0.97(2) ?
C13 C14 1.379(3) ?
C13 H131 1.01(2) ?
C14 H141 0.94(2) ?
C15 C14 1.374(3) ?
C15 H151 0.98(3) ?
C16 C15 1.386(3) ?
C16 H161 0.939(18) ?
C17 H173 1.00(3) ?
C17 H171 1.03(3) ?
C17 H172 0.95(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
C2 S1 C1 N4 0.31(15)
C2 S1 C1 N3 -178.14(15)
C1 S1 C2 N5 -0.46(17)
C10 N1 C9 C8 -174.49(17)
C17 N1 C9 C8 -0.6(3)
C10 N1 C9 C4 1.65(18)
C17 N1 C9 C4 175.52(17)
C3 N2 N3 C1 177.79(12)
N3 N2 C3 C10 178.12(14)
N3 N2 C3 C4 -1.5(2)
N2 N3 C1 N4 179.01(16)
N2 N3 C1 S1 -2.6(2)
C1 N4 N5 C2 -0.2(3)
N4 N5 C2 S1 0.5(2)
N3 C1 N4 N5 178.38(16)
S1 C1 N4 N5 -0.1(2)
N2 C3 C10 N1 -178.54(13)
C4 C3 C10 N1 1.14(17)
N2 C3 C10 C11 2.8(2)
C4 C3 C10 C11 -177.56(15)
N2 C3 C4 C5 -4.2(3)
C10 C3 C4 C5 176.13(18)
N2 C3 C4 C9 179.48(16)
C10 C3 C4 C9 -0.14(17)
C5 C4 C9 C8 -1.5(2)
C3 C4 C9 C8 175.51(16)
C5 C4 C9 N1 -177.90(14)
C3 C4 C9 N1 -0.88(17)
C9 C4 C5 C6 2.0(2)
C3 C4 C5 C6 -173.94(18)
C4 C5 C6 C7 -0.8(3)
C8 C7 C6 C5 -1.0(3)
C6 C7 C8 C9 1.4(3)
N1 C9 C8 C7 175.44(18)
C4 C9 C8 C7 -0.2(3)
C3 C10 N1 C9 -1.72(17)
C11 C10 N1 C9 177.06(14)
C3 C10 N1 C17 -175.16(18)
C11 C10 N1 C17 3.6(3)
C12 C11 C10 N1 -131.42(17)
C16 C11 C10 N1 50.4(2)
C12 C11 C10 C3 47.1(2)
C16 C11 C10 C3 -131.13(18)
C16 C11 C12 C13 0.2(3)
C10 C11 C12 C13 -178.04(16)
C12 C11 C16 C15 -0.9(3)
C10 C11 C16 C15 177.29(16)
C11 C12 C13 C14 1.0(3)
C12 C13 C14 C15 -1.6(3)
C16 C15 C14 C13 0.9(3)
C11 C16 C15 C14 0.4(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21178043
