##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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 2.4.    #
#                                                                            #
# 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                                                              #
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# This file may be used for bona fide research purposes within the           #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2008-03-19
_journal_date_accepted     2008-04-20
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      5
_journal_page_first     o912
_journal_page_last     o912
_journal_paper_category     QO
_journal_coeditor_code     BT2687
_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
;
1-(2-Hydroxy-5-methylphenyl)ethanone [(1H-indol-3-yl)acetyl]hydrazone
;
loop_
    _publ_author_name
    _publ_author_address
    'Ali, Hapipah M.'
;
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
    'Zuraini, Kadir'
;
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
    'Wan Jeffrey, Basirun'
;
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
    'Rizal, Mohd. Razali'
;
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
    'Ng, Seik Weng'
;
     Department of Chemistry
     University of Malaya
     50603 Kuala Lumpur
     Malaysia
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
1-(2-Hydroxy-5-methylphenyl)ethanone [(1H-indol-3-yl)acetyl]hydrazone
;
_chemical_name_common     ?
_chemical_formula_moiety     'C19 H19 N3 O2'
_chemical_formula_sum     'C19 H19 N3 O2'
_chemical_formula_iupac     'C19 H19 N3 O2'
_chemical_formula_weight     321.37
_chemical_melting_point     ?
_symmetry_cell_setting     Triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     4.6812(9)
_cell_length_b     12.419(3)
_cell_length_c     14.202(3)
_cell_angle_alpha     109.919(3)
_cell_angle_beta     91.710(3)
_cell_angle_gamma     90.751(3)
_cell_volume     775.7(3)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     985
_cell_measurement_theta_min     3.0
_cell_measurement_theta_max     28.3
_cell_measurement_temperature     100(2)
_exptl_crystal_description     Plate
_exptl_crystal_colour     'Pale yellow'
_exptl_crystal_size_max     0.40
_exptl_crystal_size_mid     0.13
_exptl_crystal_size_min     0.05
_exptl_crystal_density_diffrn     1.376
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     340
_exptl_absorpt_coefficient_mu     0.091
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_diffrn_ambient_temperature     100(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 SMART APEXII'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     4854
_diffrn_reflns_av_R_equivalents     0.0515
_diffrn_reflns_av_sigmaI/netI     0.1135
_diffrn_reflns_theta_min     1.53
_diffrn_reflns_theta_max     27.50
_diffrn_reflns_theta_full     27.50
_diffrn_measured_fraction_theta_max     0.985
_diffrn_measured_fraction_theta_full     0.985
_diffrn_reflns_limit_h_min     -6
_diffrn_reflns_limit_h_max     3
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     16
_diffrn_reflns_limit_l_min     -17
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_reflns_number_total     3490
_reflns_number_gt     1905
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1278
_refine_ls_R_factor_gt     0.0602
_refine_ls_wR_factor_gt     0.1435
_refine_ls_wR_factor_ref     0.1961
_refine_ls_goodness_of_fit_ref     1.010
_refine_ls_restrained_S_all     1.009
_refine_ls_number_reflns     3490
_refine_ls_number_parameters     231
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0894P)²] 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     0.427
_refine_diff_density_min     -0.459
_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     'APEX2 (Bruker, 2007)'
_computing_cell_refinement     'SAINT (Bruker, 2007)'
_computing_data_reduction     'SAINT (Bruker, 2007)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'X-SEED (Barbour, 2001)'
_computing_publication_material     'publCIF (Westrip, 2008)'
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 -0.1765(5) 0.39859(17) 0.64793(15) 0.0232(5) Uani d D 1 . .
    H H1O -0.097(9) 0.335(2) 0.617(3) 0.072(15) Uiso d D 1 . .
    O O2 0.5909(4) 0.08863(17) 0.43759(15) 0.0259(5) Uani d . 1 . .
    N N1 0.0800(5) 0.21073(19) 0.61339(17) 0.0198(5) Uani d . 1 . .
    N N2 0.2703(5) 0.1345(2) 0.55630(18) 0.0205(6) Uani d D 1 . .
    H H2N 0.287(9) 0.0706(17) 0.565(3) 0.055(12) Uiso d D 1 . .
    N N3 0.8788(6) 0.3894(2) 0.33999(18) 0.0224(6) Uani d D 1 . .
    H H3N 0.989(6) 0.4440(19) 0.339(2) 0.021(8) Uiso d D 1 . .
    C C1 -0.2982(6) 0.3739(2) 0.7244(2) 0.0201(6) Uani d . 1 . .
    C C2 -0.4852(6) 0.4525(3) 0.7818(2) 0.0241(7) Uani d . 1 . .
    H H2 -0.5215 0.5206 0.7676 0.029 Uiso calc R 1 . .
    C C3 -0.6195(6) 0.4327(3) 0.8597(2) 0.0251(7) Uani d . 1 . .
    H H3 -0.7480 0.4874 0.8985 0.030 Uiso calc R 1 . .
    C C4 -0.5699(6) 0.3340(3) 0.8822(2) 0.0243(7) Uani d . 1 . .
    C C5 -0.3819(6) 0.2562(3) 0.8235(2) 0.0226(7) Uani d . 1 . .
    H H5 -0.3487 0.1879 0.8377 0.027 Uiso calc R 1 . .
    C C6 -0.2391(6) 0.2731(2) 0.7447(2) 0.0184(6) Uani d . 1 . .
    C C7 -0.7165(7) 0.3105(3) 0.9666(2) 0.0302(8) Uani d . 1 . .
    H H7A -0.5727 0.2956 1.0119 0.045 Uiso calc R 1 . .
    H H7B -0.8452 0.2434 0.9390 0.045 Uiso calc R 1 . .
    H H7C -0.8269 0.3772 1.0037 0.045 Uiso calc R 1 . .
    C C8 -0.0378(6) 0.1881(2) 0.6856(2) 0.0196(6) Uani d . 1 . .
    C C9 0.0212(7) 0.0829(2) 0.7102(2) 0.0282(7) Uani d . 1 . .
    H H9A 0.2248 0.0659 0.7027 0.042 Uiso calc R 1 . .
    H H9B -0.0926 0.0183 0.6646 0.042 Uiso calc R 1 . .
    H H9C -0.0299 0.0952 0.7794 0.042 Uiso calc R 1 . .
    C C10 0.4156(6) 0.1572(2) 0.4841(2) 0.0199(6) Uani d . 1 . .
    C C11 0.3479(6) 0.2641(2) 0.4612(2) 0.0216(6) Uani d . 1 . .
    H H11A 0.1536 0.2549 0.4296 0.026 Uiso calc R 1 . .
    H H11B 0.3454 0.3294 0.5251 0.026 Uiso calc R 1 . .
    C C12 0.5528(6) 0.2925(2) 0.3940(2) 0.0201(6) Uani d . 1 . .
    C C13 0.7169(6) 0.3905(2) 0.4185(2) 0.0216(6) Uani d . 1 . .
    H H13 0.7181 0.4508 0.4813 0.026 Uiso calc R 1 . .
    C C14 0.6163(6) 0.2267(2) 0.2925(2) 0.0207(6) Uani d . 1 . .
    C C15 0.5219(7) 0.1205(3) 0.2253(2) 0.0255(7) Uani d . 1 . .
    H H15 0.3838 0.0759 0.2444 0.031 Uiso calc R 1 . .
    C C16 0.6313(7) 0.0813(3) 0.1311(2) 0.0306(8) Uani d . 1 . .
    H H16 0.5677 0.0090 0.0851 0.037 Uiso calc R 1 . .
    C C17 0.8355(7) 0.1464(3) 0.1020(2) 0.0302(8) Uani d . 1 . .
    H H17 0.9079 0.1174 0.0365 0.036 Uiso calc R 1 . .
    C C18 0.9324(7) 0.2513(3) 0.1664(2) 0.0274(7) Uani d . 1 . .
    H H18 1.0698 0.2956 0.1467 0.033 Uiso calc R 1 . .
    C C19 0.8215(6) 0.2900(3) 0.2617(2) 0.0231(7) Uani d . 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
    O1 C1 . 1.364(3) ?
    O1 H1O . 0.85(3) ?
    O2 C10 . 1.226(3) ?
    N1 C8 . 1.288(3) ?
    N1 N2 . 1.375(3) ?
    N2 C10 . 1.352(4) ?
    N2 H2N . 0.85(3) ?
    N3 C13 . 1.363(4) ?
    N3 C19 . 1.367(4) ?
    N3 H3N . 0.85(3) ?
    C1 C2 . 1.381(4) ?
    C1 C6 . 1.406(4) ?
    C2 C3 . 1.379(4) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.389(4) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.386(4) ?
    C4 C7 . 1.508(4) ?
    C5 C6 . 1.394(4) ?
    C5 H5 . 0.9500 ?
    C6 C8 . 1.475(4) ?
    C7 H7A . 0.9800 ?
    C7 H7B . 0.9800 ?
    C7 H7C . 0.9800 ?
    C8 C9 . 1.491(4) ?
    C9 H9A . 0.9800 ?
    C9 H9B . 0.9800 ?
    C9 H9C . 0.9800 ?
    C10 C11 . 1.505(4) ?
    C11 C12 . 1.494(4) ?
    C11 H11A . 0.9900 ?
    C11 H11B . 0.9900 ?
    C12 C13 . 1.365(4) ?
    C12 C14 . 1.436(4) ?
    C13 H13 . 0.9500 ?
    C14 C15 . 1.396(4) ?
    C14 C19 . 1.404(4) ?
    C15 C16 . 1.376(4) ?
    C15 H15 . 0.9500 ?
    C16 C17 . 1.404(5) ?
    C16 H16 . 0.9500 ?
    C17 C18 . 1.374(4) ?
    C17 H17 . 0.9500 ?
    C18 C19 . 1.392(4) ?
    C18 H18 . 0.9500 ?
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 O1 H1O . . 101(3) ?
    C8 N1 N2 . . 118.6(2) ?
    C10 N2 N1 . . 121.3(2) ?
    C10 N2 H2N . . 121(3) ?
    N1 N2 H2N . . 118(3) ?
    C13 N3 C19 . . 109.0(2) ?
    C13 N3 H3N . . 125(2) ?
    C19 N3 H3N . . 126(2) ?
    O1 C1 C2 . . 117.0(3) ?
    O1 C1 C6 . . 122.2(2) ?
    C2 C1 C6 . . 120.8(3) ?
    C3 C2 C1 . . 120.4(3) ?
    C3 C2 H2 . . 119.8 ?
    C1 C2 H2 . . 119.8 ?
    C2 C3 C4 . . 121.0(3) ?
    C2 C3 H3 . . 119.5 ?
    C4 C3 H3 . . 119.5 ?
    C5 C4 C3 . . 117.7(3) ?
    C5 C4 C7 . . 120.6(3) ?
    C3 C4 C7 . . 121.8(3) ?
    C4 C5 C6 . . 123.4(3) ?
    C4 C5 H5 . . 118.3 ?
    C6 C5 H5 . . 118.3 ?
    C5 C6 C1 . . 116.8(3) ?
    C5 C6 C8 . . 121.1(3) ?
    C1 C6 C8 . . 122.1(3) ?
    C4 C7 H7A . . 109.5 ?
    C4 C7 H7B . . 109.5 ?
    H7A C7 H7B . . 109.5 ?
    C4 C7 H7C . . 109.5 ?
    H7A C7 H7C . . 109.5 ?
    H7B C7 H7C . . 109.5 ?
    N1 C8 C6 . . 116.3(3) ?
    N1 C8 C9 . . 123.2(3) ?
    C6 C8 C9 . . 120.5(2) ?
    C8 C9 H9A . . 109.5 ?
    C8 C9 H9B . . 109.5 ?
    H9A C9 H9B . . 109.5 ?
    C8 C9 H9C . . 109.5 ?
    H9A C9 H9C . . 109.5 ?
    H9B C9 H9C . . 109.5 ?
    O2 C10 N2 . . 119.0(3) ?
    O2 C10 C11 . . 122.4(3) ?
    N2 C10 C11 . . 118.6(2) ?
    C12 C11 C10 . . 114.4(2) ?
    C12 C11 H11A . . 108.7 ?
    C10 C11 H11A . . 108.7 ?
    C12 C11 H11B . . 108.7 ?
    C10 C11 H11B . . 108.7 ?
    H11A C11 H11B . . 107.6 ?
    C13 C12 C14 . . 106.0(3) ?
    C13 C12 C11 . . 125.4(3) ?
    C14 C12 C11 . . 128.6(3) ?
    N3 C13 C12 . . 110.4(3) ?
    N3 C13 H13 . . 124.8 ?
    C12 C13 H13 . . 124.8 ?
    C15 C14 C19 . . 118.7(3) ?
    C15 C14 C12 . . 134.3(3) ?
    C19 C14 C12 . . 107.0(3) ?
    C16 C15 C14 . . 119.2(3) ?
    C16 C15 H15 . . 120.4 ?
    C14 C15 H15 . . 120.4 ?
    C15 C16 C17 . . 121.0(3) ?
    C15 C16 H16 . . 119.5 ?
    C17 C16 H16 . . 119.5 ?
    C18 C17 C16 . . 121.2(3) ?
    C18 C17 H17 . . 119.4 ?
    C16 C17 H17 . . 119.4 ?
    C17 C18 C19 . . 117.5(3) ?
    C17 C18 H18 . . 121.3 ?
    C19 C18 H18 . . 121.3 ?
    N3 C19 C18 . . 129.9(3) ?
    N3 C19 C14 . . 107.6(2) ?
    C18 C19 C14 . . 122.4(3) ?
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
    O1 H1o N1 . 0.85(3) 1.75(2) 2.540(3) 153(4) yes
    N2 H2n O2 2_656 0.85(3) 2.05(3) 2.884(3) 166(4) yes
    N3 H3n O1 2_666 0.85(3) 2.08(3) 2.913(3) 166(3) yes
