##############################################################################
###                                                                        ###
###        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/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2006-09-12
_journal_date_accepted     2006-09-12
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue     10
_journal_page_first     o4525
_journal_page_last     o4526
_journal_paper_category     EO
_journal_coeditor_code     XU2124
_publ_contact_author
;
     Dr. Seik Weng Ng
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
_publ_contact_author_email     seikweng@um.edu.my
_publ_contact_author_fax     '03 7967 4193'
_publ_contact_author_phone     '03 7967 6778'
_publ_section_title
;
2-Methyl-1H-indole-3-carbaldehyde 2-thienoylhydrazone
;
loop_
    _publ_author_name
    _publ_author_address
    'Ali, Hapipah M.'
;
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
    'Najwa, Mohd Idris'
;
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
    'Xie, Ming-Jin'
;
     School Chemistry
     Yunnan University
     Kunming 650092
     People's Republic of China
;
    'Ng, Seik Weng'
;
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2-Methyl-1H-indole-3-carbaldehyde 2-thienoylhydrazone
;
_chemical_name_common     ?
_chemical_formula_moiety     'C15 H13 N3 O S'
_chemical_formula_sum     'C15 H13 N3 O S'
_chemical_formula_iupac     'C15 H13 N3 O S'
_chemical_formula_weight     283.34
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
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'
_cell_length_a     11.688(2)
_cell_length_b     11.546(2)
_cell_length_c     10.133(2)
_cell_angle_alpha     90.00
_cell_angle_beta     94.694(2)
_cell_angle_gamma     90.00
_cell_volume     1362.8(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     1415
_cell_measurement_theta_min     2.5
_cell_measurement_theta_max     20.8
_cell_measurement_temperature     295(2)
_exptl_crystal_description     block
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.24
_exptl_crystal_size_mid     0.23
_exptl_crystal_size_min     0.20
_exptl_crystal_density_diffrn     1.381
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     592
_exptl_absorpt_coefficient_mu     0.236
_exptl_absorpt_correction_type     None
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_diffrn_ambient_temperature     295(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     'Bruker APEX-II area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     11514
_diffrn_reflns_av_R_equivalents     0.078
_diffrn_reflns_av_sigmaI/netI     0.077
_diffrn_reflns_theta_min     1.8
_diffrn_reflns_theta_max     26.4
_diffrn_reflns_theta_full     26.4
_diffrn_measured_fraction_theta_max     1.00
_diffrn_measured_fraction_theta_full     1.00
_diffrn_reflns_limit_h_min     -14
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     12
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_reflns_number_total     2793
_reflns_number_gt     1420
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.153
_refine_ls_R_factor_gt     0.075
_refine_ls_wR_factor_gt     0.172
_refine_ls_wR_factor_ref     0.209
_refine_ls_goodness_of_fit_ref     1.02
_refine_ls_restrained_S_all     1.02
_refine_ls_number_reflns     2793
_refine_ls_number_parameters     170
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0979P)²+0.3022P] 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     0.37
_refine_diff_density_min     -0.31
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
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'
    'O' 'O' 0.0106 0.0060
                         '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     'APEXII (Bruker, 2004)'
_computing_cell_refinement     'SAINT (Bruker, 2004)'
_computing_data_reduction     SAINT
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'X-SEED (Barbour, 2001)'
_computing_publication_material     SHELXL97
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 0.45706(10) 0.92616(10) 0.73323(11) 0.0697(4) Uani d . 1 . .
    O O1 0.6319(2) 0.7454(2) 0.7868(3) 0.0626(8) Uani d . 1 . .
    N N1 0.6354(3) 0.6811(3) 0.5739(3) 0.0620(9) Uani d . 1 . .
    H H1N 0.6078 0.6867 0.4929 0.074 Uiso calc R 1 . .
    N N2 0.7227(3) 0.6032(3) 0.6084(3) 0.0598(9) Uani d . 1 . .
    N N3 0.9457(3) 0.2966(3) 0.4867(4) 0.0646(10) Uani d . 1 . .
    H H3N 0.9738 0.2388 0.4466 0.078 Uiso calc R 1 . .
    C C1 0.3534(4) 0.9786(4) 0.6195(4) 0.0727(13) Uani d . 1 . .
    H H1 0.3041 1.0391 0.6362 0.087 Uiso calc R 1 . .
    C C2 0.3516(4) 0.9229(4) 0.5044(5) 0.0769(14) Uani d . 1 . .
    H H2 0.3005 0.9403 0.4319 0.092 Uiso calc R 1 . .
    C C3 0.4352(4) 0.8345(4) 0.5035(4) 0.0705(13) Uani d . 1 . .
    H H3 0.4451 0.7875 0.4308 0.085 Uiso calc R 1 . .
    C C4 0.4998(3) 0.8261(3) 0.6221(4) 0.0575(11) Uani d . 1 . .
    C C5 0.5937(3) 0.7485(4) 0.6681(4) 0.0546(10) Uani d . 1 . .
    C C6 0.7387(3) 0.5277(4) 0.5156(4) 0.0598(11) Uani d . 1 . .
    H H6 0.6909 0.5286 0.4375 0.072 Uiso calc R 1 . .
    C C7 0.8302(3) 0.4424(3) 0.5327(4) 0.0540(10) Uani d . 1 . .
    C C8 0.8477(3) 0.3562(4) 0.4427(4) 0.0591(11) Uani d . 1 . .
    C C9 0.7834(4) 0.3214(4) 0.3167(4) 0.0749(13) Uani d . 1 . .
    H H9A 0.7693 0.2395 0.3176 0.112 Uiso calc R 1 . .
    H H9B 0.8276 0.3403 0.2439 0.112 Uiso calc R 1 . .
    H H9C 0.7115 0.3620 0.3071 0.112 Uiso calc R 1 . .
    C C10 0.9917(2) 0.3428(2) 0.6028(2) 0.0592(11) Uani d G 1 . .
    C C11 1.0898(2) 0.3142(2) 0.6830(3) 0.0719(13) Uani d G 1 . .
    H H11 1.1366 0.2539 0.6591 0.086 Uiso calc R 1 . .
    C C12 1.1179(2) 0.3758(3) 0.7991(3) 0.0757(14) Uani d G 1 . .
    H H12 1.1835 0.3566 0.8528 0.091 Uiso calc R 1 . .
    C C13 1.0479(3) 0.4659(3) 0.8348(2) 0.0701(12) Uani d G 1 . .
    H H13 1.0668 0.5071 0.9124 0.084 Uiso calc R 1 . .
    C C14 0.9499(2) 0.4946(2) 0.7545(3) 0.0629(12) Uani d G 1 . .
    H H14 0.9031 0.5549 0.7785 0.076 Uiso calc R 1 . .
    C C15 0.92173(18) 0.4330(2) 0.6385(3) 0.0533(10) Uani d G 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 0.0737(8) 0.0623(8) 0.0727(8) 0.0066(6) 0.0034(6) -0.0106(6)
    O1 0.0598(17) 0.0609(18) 0.0678(19) 0.0039(14) 0.0091(14) -0.0019(15)
    N1 0.059(2) 0.066(2) 0.061(2) 0.0119(19) 0.0065(17) 0.0032(18)
    N2 0.053(2) 0.051(2) 0.075(2) 0.0096(17) 0.0049(17) 0.0099(18)
    N3 0.070(2) 0.043(2) 0.083(3) 0.0069(18) 0.021(2) -0.0063(18)
    C1 0.069(3) 0.067(3) 0.081(3) 0.013(2) 0.002(2) -0.004(3)
    C2 0.071(3) 0.086(4) 0.072(3) 0.020(3) -0.006(2) 0.001(3)
    C3 0.071(3) 0.078(3) 0.063(3) 0.009(3) 0.007(2) -0.010(2)
    C4 0.049(2) 0.054(3) 0.070(3) 0.002(2) 0.008(2) 0.004(2)
    C5 0.057(3) 0.054(3) 0.055(3) -0.012(2) 0.015(2) -0.009(2)
    C6 0.060(3) 0.049(3) 0.073(3) 0.001(2) 0.016(2) 0.004(2)
    C7 0.056(2) 0.037(2) 0.072(3) 0.0025(19) 0.020(2) 0.005(2)
    C8 0.060(3) 0.047(2) 0.072(3) -0.002(2) 0.019(2) 0.006(2)
    C9 0.082(3) 0.066(3) 0.078(3) -0.007(3) 0.014(3) -0.005(2)
    C10 0.052(2) 0.042(2) 0.086(3) 0.003(2) 0.019(2) 0.011(2)
    C11 0.060(3) 0.045(3) 0.112(4) 0.004(2) 0.019(3) 0.018(3)
    C12 0.056(3) 0.078(3) 0.093(4) -0.003(3) 0.004(2) 0.026(3)
    C13 0.056(3) 0.070(3) 0.085(3) -0.006(2) 0.007(2) 0.005(3)
    C14 0.054(3) 0.050(3) 0.087(3) 0.004(2) 0.019(2) 0.002(2)
    C15 0.055(2) 0.036(2) 0.072(3) -0.0046(19) 0.018(2) 0.005(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 C1 . 1.713(5) no
    S1 C4 . 1.716(4) no
    O1 C5 . 1.249(4) no
    N1 C5 . 1.353(5) no
    N1 N2 . 1.383(4) no
    N1 H1N . 0.8600 no
    N2 C6 . 1.307(5) no
    N3 C10 . 1.362(4) no
    N3 C8 . 1.379(5) no
    N3 H3N . 0.8600 no
    C1 C2 . 1.330(6) no
    C1 H1 . 0.9300 no
    C2 C3 . 1.413(6) no
    C2 H2 . 0.9300 no
    C3 C4 . 1.370(5) no
    C3 H3 . 0.9300 no
    C4 C5 . 1.463(6) no
    C6 C7 . 1.454(5) no
    C6 H6 . 0.9300 no
    C7 C8 . 1.376(5) no
    C7 C15 . 1.455(5) no
    C8 C9 . 1.483(6) no
    C9 H9A . 0.9600 no
    C9 H9B . 0.9600 no
    C9 H9C . 0.9600 no
    C10 C11 . 1.3900 no
    C10 C15 . 1.3900 no
    C11 C12 . 1.3900 no
    C11 H11 . 0.9300 no
    C12 C13 . 1.3900 no
    C12 H12 . 0.9300 no
    C13 C14 . 1.3900 no
    C13 H13 . 0.9300 no
    C14 C15 . 1.3900 no
    C14 H14 . 0.9300 no
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
    C1 S1 C4 . . 91.4(2) no
    C5 N1 N2 . . 119.8(3) no
    C5 N1 H1N . . 120.1 no
    N2 N1 H1N . . 120.1 no
    C6 N2 N1 . . 113.4(3) no
    C10 N3 C8 . . 110.0(3) no
    C10 N3 H3N . . 125.0 no
    C8 N3 H3N . . 125.0 no
    C2 C1 S1 . . 112.2(4) no
    C2 C1 H1 . . 123.9 no
    S1 C1 H1 . . 123.9 no
    C1 C2 C3 . . 113.2(4) no
    C1 C2 H2 . . 123.4 no
    C3 C2 H2 . . 123.4 no
    C4 C3 C2 . . 112.2(4) no
    C4 C3 H3 . . 123.9 no
    C2 C3 H3 . . 123.9 no
    C3 C4 C5 . . 131.9(4) no
    C3 C4 S1 . . 111.0(3) no
    C5 C4 S1 . . 117.0(3) no
    O1 C5 N1 . . 122.8(4) no
    O1 C5 C4 . . 121.6(4) no
    N1 C5 C4 . . 115.6(4) no
    N2 C6 C7 . . 120.9(4) no
    N2 C6 H6 . . 119.6 no
    C7 C6 H6 . . 119.6 no
    C8 C7 C6 . . 124.0(4) no
    C8 C7 C15 . . 107.1(3) no
    C6 C7 C15 . . 128.9(4) no
    C7 C8 N3 . . 108.1(4) no
    C7 C8 C9 . . 132.4(4) no
    N3 C8 C9 . . 119.5(4) no
    C8 C9 H9A . . 109.5 no
    C8 C9 H9B . . 109.5 no
    H9A C9 H9B . . 109.5 no
    C8 C9 H9C . . 109.5 no
    H9A C9 H9C . . 109.5 no
    H9B C9 H9C . . 109.5 no
    N3 C10 C11 . . 131.3(2) no
    N3 C10 C15 . . 108.7(2) no
    C11 C10 C15 . . 120.0 no
    C12 C11 C10 . . 120.0 no
    C12 C11 H11 . . 120.0 no
    C10 C11 H11 . . 120.0 no
    C13 C12 C11 . . 120.0 no
    C13 C12 H12 . . 120.0 no
    C11 C12 H12 . . 120.0 no
    C12 C13 C14 . . 120.0 no
    C12 C13 H13 . . 120.0 no
    C14 C13 H13 . . 120.0 no
    C13 C14 C15 . . 120.0 no
    C13 C14 H14 . . 120.0 no
    C15 C14 H14 . . 120.0 no
    C14 C15 C10 . . 120.0 no
    C14 C15 C7 . . 133.9(2) no
    C10 C15 C7 . . 106.0(2) no
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
    C5 N1 N2 C6 . . . . 166.6(3) no
    C4 S1 C1 C2 . . . . 0.2(4) no
    S1 C1 C2 C3 . . . . -0.1(5) no
    C1 C2 C3 C4 . . . . -0.1(6) no
    C2 C3 C4 C5 . . . . 179.2(4) no
    C2 C3 C4 S1 . . . . 0.2(5) no
    C1 S1 C4 C3 . . . . -0.2(3) no
    C1 S1 C4 C5 . . . . -179.4(3) no
    N2 N1 C5 O1 . . . . 1.3(5) no
    N2 N1 C5 C4 . . . . -178.7(3) no
    C3 C4 C5 O1 . . . . -170.6(4) no
    S1 C4 C5 O1 . . . . 8.3(5) no
    C3 C4 C5 N1 . . . . 9.4(6) no
    S1 C4 C5 N1 . . . . -171.7(3) no
    N1 N2 C6 C7 . . . . 177.4(3) no
    N2 C6 C7 C8 . . . . 175.9(4) no
    N2 C6 C7 C15 . . . . -7.3(6) no
    C6 C7 C8 N3 . . . . 176.1(3) no
    C15 C7 C8 N3 . . . . -1.2(4) no
    C6 C7 C8 C9 . . . . -3.4(7) no
    C15 C7 C8 C9 . . . . 179.3(4) no
    C10 N3 C8 C7 . . . . -0.1(4) no
    C10 N3 C8 C9 . . . . 179.5(3) no
    C8 N3 C10 C11 . . . . -178.9(2) no
    C8 N3 C10 C15 . . . . 1.4(3) no
    N3 C10 C11 C12 . . . . -179.7(3) no
    C15 C10 C11 C12 . . . . 0.0 no
    C10 C11 C12 C13 . . . . 0.0 no
    C11 C12 C13 C14 . . . . 0.0 no
    C12 C13 C14 C15 . . . . 0.0 no
    C13 C14 C15 C10 . . . . 0.0 no
    C13 C14 C15 C7 . . . . -177.6(3) no
    N3 C10 C15 C14 . . . . 179.8(3) no
    C11 C10 C15 C14 . . . . 0.0 no
    N3 C10 C15 C7 . . . . -2.0(2) no
    C11 C10 C15 C7 . . . . 178.2(2) no
    C8 C7 C15 C14 . . . . 179.8(2) no
    C6 C7 C15 C14 . . . . 2.7(5) no
    C8 C7 C15 C10 . . . . 2.0(3) no
    C6 C7 C15 C10 . . . . -175.2(3) no
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
    N1 H1N O1 4_575 0.86 2.27 3.027(4) 147 yes
