##############################################################################
###                                                                        ###
###        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     2006-09-13
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2006
_journal_volume     62
_journal_issue     10
_journal_page_first     o4527
_journal_page_last     o4528
_journal_paper_category     EO
_journal_coeditor_code     XU2125
_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 4-hydrobenzoylhydrazone
;
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 4-hydrobenzoylhydrazone
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H15 N3 O2'
_chemical_formula_sum     'C17 H15 N3 O2'
_chemical_formula_iupac     'C17 H15 N3 O2'
_chemical_formula_weight     293.32
_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     12.1710(10)
_cell_length_b     14.0900(10)
_cell_length_c     8.6767(7)
_cell_angle_alpha     90.00
_cell_angle_beta     97.9170(10)
_cell_angle_gamma     90.00
_cell_volume     1473.8(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3602
_cell_measurement_theta_min     2.7
_cell_measurement_theta_max     27.1
_cell_measurement_temperature     295(2)
_exptl_crystal_description     Block
_exptl_crystal_colour     Yellow
_exptl_crystal_size_max     0.31
_exptl_crystal_size_mid     0.27
_exptl_crystal_size_min     0.24
_exptl_crystal_density_diffrn     1.322
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     616
_exptl_absorpt_coefficient_mu     0.089
_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     13436
_diffrn_reflns_av_R_equivalents     0.024
_diffrn_reflns_av_sigmaI/netI     0.021
_diffrn_reflns_theta_min     1.7
_diffrn_reflns_theta_max     27.1
_diffrn_reflns_theta_full     27.1
_diffrn_measured_fraction_theta_max     1.00
_diffrn_measured_fraction_theta_full     1.00
_diffrn_reflns_limit_h_min     -15
_diffrn_reflns_limit_h_max     15
_diffrn_reflns_limit_k_min     -18
_diffrn_reflns_limit_k_max     17
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     11
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_reflns_number_total     3236
_reflns_number_gt     2516
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.058
_refine_ls_R_factor_gt     0.043
_refine_ls_wR_factor_gt     0.113
_refine_ls_wR_factor_ref     0.124
_refine_ls_goodness_of_fit_ref     1.04
_refine_ls_restrained_S_all     1.04
_refine_ls_number_reflns     3236
_refine_ls_number_parameters     212
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0604P)²+0.3578P] 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     -0.18
_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'
_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
    O O1 0.84504(9) 0.34132(7) 0.17384(13) 0.0409(3) Uani d . 1 . .
    O O2 1.20818(10) 0.01865(9) 0.24474(17) 0.0573(4) Uani d D 1 . .
    N N1 0.38547(11) 0.41537(10) 0.57821(17) 0.0414(3) Uani d D 1 . .
    N N2 0.69363(10) 0.31756(9) 0.37014(15) 0.0384(3) Uani d . 1 . .
    N N3 0.79539(10) 0.27054(10) 0.38769(15) 0.0375(3) Uani d D 1 . .
    C C1 0.35856(12) 0.40528(11) 0.41970(19) 0.0397(4) Uani d . 1 . .
    C C2 0.25948(13) 0.42349(13) 0.3244(2) 0.0504(4) Uani d . 1 . .
    H H2 0.1983 0.4477 0.3648 0.060 Uiso calc R 1 . .
    C C3 0.25515(15) 0.40439(14) 0.1683(2) 0.0551(5) Uani d . 1 . .
    H H3 0.1899 0.4161 0.1018 0.066 Uiso calc R 1 . .
    C C4 0.34674(15) 0.36786(14) 0.1077(2) 0.0529(5) Uani d . 1 . .
    H H4 0.3408 0.3541 0.0021 0.063 Uiso calc R 1 . .
    C C5 0.44613(14) 0.35180(12) 0.20179(19) 0.0441(4) Uani d . 1 . .
    H H5 0.5073 0.3289 0.1599 0.053 Uiso calc R 1 . .
    C C6 0.45318(12) 0.37055(10) 0.36088(18) 0.0363(3) Uani d . 1 . .
    C C7 0.53855(12) 0.36143(10) 0.49330(18) 0.0352(3) Uani d . 1 . .
    C C8 0.49272(13) 0.38906(11) 0.62371(18) 0.0372(3) Uani d . 1 . .
    C C9 0.54119(15) 0.39250(13) 0.79001(19) 0.0476(4) Uani d . 1 . .
    H H9A 0.5161 0.4487 0.8370 0.071 Uiso calc R 1 . .
    H H9B 0.6206 0.3935 0.7981 0.071 Uiso calc R 1 . .
    H H9C 0.5182 0.3375 0.8426 0.071 Uiso calc R 1 . .
    C C10 0.64946(12) 0.32637(11) 0.49603(18) 0.0373(3) Uani d . 1 . .
    H H10 0.6903 0.3096 0.5907 0.045 Uiso calc R 1 . .
    C C11 0.86110(12) 0.27882(10) 0.27744(17) 0.0334(3) Uani d . 1 . .
    C C12 0.95165(12) 0.20881(10) 0.27749(17) 0.0344(3) Uani d . 1 . .
    C C13 1.04665(14) 0.23511(12) 0.2159(2) 0.0520(5) Uani d . 1 . .
    H H13 1.0531 0.2968 0.1802 0.062 Uiso calc R 1 . .
    C C14 1.13141(15) 0.17167(13) 0.2066(3) 0.0592(5) Uani d . 1 . .
    H H14 1.1950 0.1911 0.1672 0.071 Uiso calc R 1 . .
    C C15 1.12213(13) 0.07866(11) 0.2561(2) 0.0418(4) Uani d . 1 . .
    C C16 1.02722(13) 0.05080(11) 0.31556(19) 0.0408(4) Uani d . 1 . .
    H H16 1.0199 -0.0116 0.3478 0.049 Uiso calc R 1 . .
    C C17 0.94358(12) 0.11526(11) 0.32704(19) 0.0395(4) Uani d . 1 . .
    H H17 0.8807 0.0960 0.3685 0.047 Uiso calc R 1 . .
    H H2O 1.195(2) -0.0380(9) 0.272(3) 0.085(8) Uiso d D 1 . .
    H H1N 0.3430(14) 0.4410(13) 0.6382(19) 0.056(5) Uiso d D 1 . .
    H H3N 0.8115(17) 0.2345(13) 0.4680(17) 0.064(6) Uiso d D 1 . .
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
    O1 C11 . 1.2543(18) no
    O2 C15 . 1.3603(19) no
    O2 H2O . 0.854(10) no
    N1 C8 . 1.362(2) no
    N1 C1 . 1.377(2) no
    N1 H1N . 0.862(9) no
    N2 C10 . 1.2881(19) no
    N2 N3 . 1.3943(17) no
    N3 C11 . 1.3338(18) no
    N3 H3N . 0.863(9) no
    C1 C2 . 1.389(2) no
    C1 C6 . 1.410(2) no
    C2 C3 . 1.375(3) no
    C2 H2 . 0.9300 no
    C3 C4 . 1.395(3) no
    C3 H3 . 0.9300 no
    C4 C5 . 1.381(2) no
    C4 H4 . 0.9300 no
    C5 C6 . 1.396(2) no
    C5 H5 . 0.9300 no
    C6 C7 . 1.445(2) no
    C7 C8 . 1.385(2) no
    C7 C10 . 1.435(2) no
    C8 C9 . 1.483(2) no
    C9 H9A . 0.9600 no
    C9 H9B . 0.9600 no
    C9 H9C . 0.9600 no
    C10 H10 . 0.9300 no
    C11 C12 . 1.479(2) no
    C12 C13 . 1.389(2) no
    C12 C17 . 1.394(2) no
    C13 C14 . 1.376(2) no
    C13 H13 . 0.9300 no
    C14 C15 . 1.388(2) no
    C14 H14 . 0.9300 no
    C15 C16 . 1.385(2) no
    C16 C17 . 1.378(2) no
    C16 H16 . 0.9300 no
    C17 H17 . 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
    C15 O2 H2O . . 112.8(16) no
    C8 N1 C1 . . 110.37(12) no
    C8 N1 H1N . . 124.7(13) no
    C1 N1 H1N . . 124.5(13) no
    C10 N2 N3 . . 114.92(13) no
    C11 N3 N2 . . 119.44(13) no
    C11 N3 H3N . . 122.6(14) no
    N2 N3 H3N . . 117.9(14) no
    N1 C1 C2 . . 130.03(14) no
    N1 C1 C6 . . 107.68(14) no
    C2 C1 C6 . . 122.29(16) no
    C3 C2 C1 . . 117.55(16) no
    C3 C2 H2 . . 121.2 no
    C1 C2 H2 . . 121.2 no
    C2 C3 C4 . . 121.29(17) no
    C2 C3 H3 . . 119.4 no
    C4 C3 H3 . . 119.4 no
    C5 C4 C3 . . 121.20(18) no
    C5 C4 H4 . . 119.4 no
    C3 C4 H4 . . 119.4 no
    C4 C5 C6 . . 118.85(16) no
    C4 C5 H5 . . 120.6 no
    C6 C5 H5 . . 120.6 no
    C5 C6 C1 . . 118.78(15) no
    C5 C6 C7 . . 135.14(14) no
    C1 C6 C7 . . 106.07(13) no
    C8 C7 C10 . . 124.58(15) no
    C8 C7 C6 . . 107.35(13) no
    C10 C7 C6 . . 128.01(14) no
    N1 C8 C7 . . 108.52(14) no
    N1 C8 C9 . . 120.68(13) no
    C7 C8 C9 . . 130.80(15) 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
    N2 C10 C7 . . 121.39(14) no
    N2 C10 H10 . . 119.3 no
    C7 C10 H10 . . 119.3 no
    O1 C11 N3 . . 121.72(13) no
    O1 C11 C12 . . 120.73(13) no
    N3 C11 C12 . . 117.51(13) no
    C13 C12 C17 . . 117.94(14) no
    C13 C12 C11 . . 118.79(14) no
    C17 C12 C11 . . 123.13(13) no
    C14 C13 C12 . . 121.32(15) no
    C14 C13 H13 . . 119.3 no
    C12 C13 H13 . . 119.3 no
    C13 C14 C15 . . 120.10(15) no
    C13 C14 H14 . . 120.0 no
    C15 C14 H14 . . 120.0 no
    O2 C15 C16 . . 122.75(14) no
    O2 C15 C14 . . 117.90(14) no
    C16 C15 C14 . . 119.35(15) no
    C17 C16 C15 . . 120.16(14) no
    C17 C16 H16 . . 119.9 no
    C15 C16 H16 . . 119.9 no
    C16 C17 C12 . . 121.11(13) no
    C16 C17 H17 . . 119.4 no
    C12 C17 H17 . . 119.4 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
    C10 N2 N3 C11 . . . . -162.72(14) no
    C8 N1 C1 C2 . . . . 179.97(16) no
    C8 N1 C1 C6 . . . . 0.17(17) no
    N1 C1 C2 C3 . . . . -178.33(17) no
    C6 C1 C2 C3 . . . . 1.4(2) no
    C1 C2 C3 C4 . . . . 0.1(3) no
    C2 C3 C4 C5 . . . . -1.7(3) no
    C3 C4 C5 C6 . . . . 1.6(3) no
    C4 C5 C6 C1 . . . . -0.1(2) no
    C4 C5 C6 C7 . . . . 178.47(17) no
    N1 C1 C6 C5 . . . . 178.33(14) no
    C2 C1 C6 C5 . . . . -1.5(2) no
    N1 C1 C6 C7 . . . . -0.60(16) no
    C2 C1 C6 C7 . . . . 179.59(15) no
    C5 C6 C7 C8 . . . . -177.86(17) no
    C1 C6 C7 C8 . . . . 0.80(16) no
    C5 C6 C7 C10 . . . . -0.6(3) no
    C1 C6 C7 C10 . . . . 178.03(14) no
    C1 N1 C8 C7 . . . . 0.35(18) no
    C1 N1 C8 C9 . . . . -179.28(14) no
    C10 C7 C8 N1 . . . . -178.06(13) no
    C6 C7 C8 N1 . . . . -0.72(17) no
    C10 C7 C8 C9 . . . . 1.5(3) no
    C6 C7 C8 C9 . . . . 178.87(16) no
    N3 N2 C10 C7 . . . . -171.49(13) no
    C8 C7 C10 N2 . . . . -167.68(15) no
    C6 C7 C10 N2 . . . . 15.5(2) no
    N2 N3 C11 O1 . . . . 14.1(2) no
    N2 N3 C11 C12 . . . . -163.49(13) no
    O1 C11 C12 C13 . . . . 29.9(2) no
    N3 C11 C12 C13 . . . . -152.55(15) no
    O1 C11 C12 C17 . . . . -145.73(15) no
    N3 C11 C12 C17 . . . . 31.9(2) no
    C17 C12 C13 C14 . . . . -1.3(3) no
    C11 C12 C13 C14 . . . . -177.11(18) no
    C12 C13 C14 C15 . . . . 1.4(3) no
    C13 C14 C15 O2 . . . . -179.96(18) no
    C13 C14 C15 C16 . . . . -0.4(3) no
    O2 C15 C16 C17 . . . . 178.75(16) no
    C14 C15 C16 C17 . . . . -0.8(3) no
    C15 C16 C17 C12 . . . . 0.9(3) no
    C13 C12 C17 C16 . . . . 0.1(2) no
    C11 C12 C17 C16 . . . . 175.72(15) 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
    O2 H2<i>o</i> O1 2_745 0.850(10)
                                   1.850(10)
                                           2.700(2) 175(2) yes
    N1 H1<i>n</i> O2 4_466 0.860(10)
                                   2.070(10)
                                           2.910(2) 164(2) yes
    N3 H3<i>n</i> O1 4_566 0.860(10)
                                   2.070(10)
                                           2.933(2) 174(2) yes
