##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
1-Methyl-2-phenyl-3-(thiadiazol-2-yldiazenyl)-1H-indole
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H13 N5 S'
_chemical_formula_sum     'C17 H13 N5 S'
_chemical_formula_iupac     'C17 H13 N5 S'
_chemical_formula_weight     319.38
_chemical_melting_point     '458-459'
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
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'
_cell_length_a     8.0288(2)
_cell_length_b     17.3757(3)
_cell_length_c     11.1899(3)
_cell_angle_alpha     90.00
_cell_angle_beta     104.4222(14)
_cell_angle_gamma     90.00
_cell_volume     1511.86(6)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     7865
_cell_measurement_theta_min     2.2
_cell_measurement_theta_max     30.5
_cell_measurement_temperature     294(2)
_exptl_crystal_description     block
_exptl_crystal_colour     orange
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.20
_exptl_crystal_size_min     0.15
_exptl_crystal_density_diffrn     1.403
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     664
_exptl_absorpt_coefficient_mu     0.221
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(Blessing, 1995)'
_exptl_absorpt_correction_T_min     0.937
_exptl_absorpt_correction_T_max     0.958
_exptl_special_details
;
;
_diffrn_ambient_temperature     294(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Rigaku R-AXIS RAPID-S'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     44017
_diffrn_reflns_av_R_equivalents     0.058
_diffrn_reflns_av_sigmaI/netI     0.036
_diffrn_reflns_theta_min     2.2
_diffrn_reflns_theta_max     30.7
_diffrn_reflns_theta_full     30.7
_diffrn_measured_fraction_theta_max     0.99
_diffrn_measured_fraction_theta_full     0.99
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -24
_diffrn_reflns_limit_k_max     24
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     4636
_reflns_number_gt     3243
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.075
_refine_ls_R_factor_gt     0.053
_refine_ls_wR_factor_gt     0.129
_refine_ls_wR_factor_ref     0.146
_refine_ls_goodness_of_fit_ref     1.052
_refine_ls_restrained_S_all     1.052
_refine_ls_number_reflns     4636
_refine_ls_number_parameters     261
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0634P)²+0.1946P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.22
_refine_diff_density_min     -0.32
_refine_ls_extinction_method     SHELXL97
_refine_ls_extinction_coef     0.072(4)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 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'
_computing_data_collection     'CrystalClear (Rigaku/MSC, 2005)'
_computing_cell_refinement     'CrystalClear'
_computing_data_reduction     'CrystalClear'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material     'WinGX (Farrugia, 1999)'
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
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    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 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 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_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_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_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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    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) ?
data_global
_journal_date_recd_electronic     2006-11-27
_journal_date_accepted     2006-12-01
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2007
_journal_volume     63
_journal_issue      1
_journal_page_first     o148
_journal_page_last     o150
_journal_paper_category     EO
_journal_coeditor_code     XU2181
_publ_contact_author
;
Dr. Tuncer Hökelek
Hacettepe University
Department of Physics
06800 Beytepe
Ankara
Turkey
;
_publ_contact_author_email     merzifon@hacettepe.edu.tr
_publ_contact_author_fax     '90(312)2352550'
_publ_contact_author_phone     '90(312)2977242'
_publ_section_title
;
1-Methyl-2-phenyl-3-(thiadiazol-2-yldiazenyl)-1H-indole
;
loop_
    _publ_author_name
    _publ_author_address
    'Seferoğlu, Zeynel'
;
Department of Chemistry
Gazi University
06500 Beşevler
Ankara
Turkey
;
    'Hökelek, Tuncer'
;
Department of Physics
Hacettepe University
06800 Beytepe
Ankara
Turkey
;
    'Şahin, Ertan'
;
Department of Chemistry
Atatürk University
22240 Erzurum
Turkey
;
    'Ertan , Nermin'
;
Department of Chemistry
Gazi University
06500 Beşevler
Ankara
Turkey
;
