##############################################################################
###                                                                        ###
###        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 2.1.    #
#                                                                            #
# 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                #
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##############################################################################
                                             
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     o4529
_journal_page_last     o4530
_journal_paper_category     EO
_journal_coeditor_code     HB2146
_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
;
5-Chloro-1H-indole-3-carbaldehyde benzoylhydrazone
;
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
;
5-Chloro-1H-indole-3-carbaldehyde benzoylhydrazone
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H12 Cl N3 O'
_chemical_formula_sum     'C16 H12 Cl N3 O'
_chemical_formula_iupac     'C16 H12 Cl N3 O'
_chemical_formula_weight     297.74
_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     11.0860(9)
_cell_length_b     5.9337(5)
_cell_length_c     21.625(2)
_cell_angle_alpha     90.00
_cell_angle_beta     95.3360(10)
_cell_angle_gamma     90.00
_cell_volume     1416.3(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3511
_cell_measurement_theta_min     2.5
_cell_measurement_theta_max     25.7
_cell_measurement_temperature     295(2)
_exptl_crystal_description     Block
_exptl_crystal_colour     Yellow
_exptl_crystal_size_max     0.34
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.24
_exptl_crystal_density_diffrn     1.396
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     616
_exptl_absorpt_coefficient_mu     0.271
_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 CCD'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     12576
_diffrn_reflns_av_R_equivalents     0.0227
_diffrn_reflns_av_sigmaI/netI     0.0205
_diffrn_reflns_theta_min     1.8
_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     -14
_diffrn_reflns_limit_h_max     14
_diffrn_reflns_limit_k_min     -7
_diffrn_reflns_limit_k_max     7
_diffrn_reflns_limit_l_min     -27
_diffrn_reflns_limit_l_max     27
_diffrn_standards_number     0
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_reflns_number_total     3131
_reflns_number_gt     2404
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.052
_refine_ls_R_factor_gt     0.037
_refine_ls_wR_factor_gt     0.095
_refine_ls_wR_factor_ref     0.106
_refine_ls_goodness_of_fit_ref     1.04
_refine_ls_restrained_S_all     1.04
_refine_ls_number_reflns     3131
_refine_ls_number_parameters     198
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0525P)²+0.2701P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     'difmap and 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     0.20
_refine_diff_density_min     -0.25
_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'
    'Cl' 'Cl' 0.1484 0.1585
                         '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
    Cl Cl1 0.58021(5) 0.02346(9) 0.66464(2) 0.07121(19) Uani d . 1 . .
    O O1 0.91244(10) 0.8269(2) 0.44111(4) 0.0502(3) Uani d . 1 . .
    N N1 0.91379(13) 0.7961(2) 0.54393(5) 0.0443(3) Uani d D 1 . .
    N N2 0.86470(12) 0.7135(2) 0.59648(5) 0.0412(3) Uani d . 1 . .
    N N3 0.85821(13) 0.7094(2) 0.80865(6) 0.0451(3) Uani d D 1 . .
    C C1 0.79003(14) 0.5325(3) 0.78332(6) 0.0395(3) Uani d . 1 . .
    C C2 0.73001(16) 0.3617(3) 0.81168(7) 0.0501(4) Uani d . 1 . .
    H H2 0.7326 0.3524 0.8547 0.060 Uiso calc R 1 . .
    C C3 0.66675(16) 0.2067(3) 0.77441(8) 0.0529(4) Uani d . 1 . .
    H H3 0.6253 0.0907 0.7922 0.063 Uiso calc R 1 . .
    C C4 0.66437(14) 0.2225(3) 0.70995(8) 0.0464(4) Uani d . 1 . .
    C C5 0.72548(13) 0.3873(3) 0.68071(7) 0.0410(4) Uani d . 1 . .
    H H5 0.7239 0.3922 0.6377 0.049 Uiso calc R 1 . .
    C C6 0.78986(13) 0.5467(3) 0.71789(6) 0.0358(3) Uani d . 1 . .
    C C7 0.86357(13) 0.7388(3) 0.70567(6) 0.0373(3) Uani d . 1 . .
    C C8 0.90156(14) 0.8312(3) 0.76245(7) 0.0429(4) Uani d . 1 . .
    H H8 0.9500 0.9588 0.7683 0.051 Uiso calc R 1 . .
    C C9 0.90033(14) 0.8142(3) 0.64702(6) 0.0400(3) Uani d . 1 . .
    H H9 0.9510 0.9387 0.6459 0.048 Uiso calc R 1 . .
    C C10 0.87112(14) 0.7348(3) 0.48638(6) 0.0390(3) Uani d . 1 . .
    C C11 0.77271(13) 0.5626(3) 0.47782(6) 0.0375(3) Uani d . 1 . .
    C C12 0.77793(15) 0.3589(3) 0.50966(7) 0.0445(4) Uani d . 1 . .
    H H12 0.8449 0.3249 0.5372 0.053 Uiso calc R 1 . .
    C C13 0.68363(17) 0.2071(3) 0.50032(8) 0.0533(4) Uani d . 1 . .
    H H13 0.6874 0.0702 0.5214 0.064 Uiso calc R 1 . .
    C C14 0.58379(16) 0.2580(3) 0.45985(8) 0.0556(5) Uani d . 1 . .
    H H14 0.5196 0.1567 0.4544 0.067 Uiso calc R 1 . .
    C C15 0.57861(15) 0.4580(3) 0.42737(8) 0.0537(4) Uani d . 1 . .
    H H15 0.5115 0.4908 0.3998 0.064 Uiso calc R 1 . .
    C C16 0.67332(14) 0.6102(3) 0.43578(7) 0.0448(4) Uani d . 1 . .
    H H16 0.6705 0.7441 0.4133 0.054 Uiso calc R 1 . .
    H H1N 0.9691(13) 0.898(3) 0.5461(9) 0.062(6) Uiso d D 1 . .
    H H3N 0.8710(18) 0.735(3) 0.8480(5) 0.067(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
    Cl1 C4 . 1.7478(17) no
    O1 C10 . 1.2451(17) no
    N1 C10 . 1.3400(18) no
    N1 N2 . 1.3938(16) no
    N1 H1N . 0.860(10)
                     no
    N2 C9 . 1.2755(19) no
    N3 C8 . 1.357(2) no
    N3 C1 . 1.377(2) no
    N3 H3N . 0.860(10)
                     no
    C1 C2 . 1.386(2) no
    C1 C6 . 1.4174(19) no
    C2 C3 . 1.372(2) no
    C2 H2 . 0.9300 no
    C3 C4 . 1.395(2) no
    C3 H3 . 0.9300 no
    C4 C5 . 1.377(2) no
    C5 C6 . 1.394(2) no
    C5 H5 . 0.9300 no
    C6 C7 . 1.441(2) no
    C7 C8 . 1.375(2) no
    C7 C9 . 1.4393(19) no
    C8 H8 . 0.9300 no
    C9 H9 . 0.9300 no
    C10 C11 . 1.494(2) no
    C11 C12 . 1.389(2) no
    C11 C16 . 1.391(2) no
    C12 C13 . 1.381(2) no
    C12 H12 . 0.9300 no
    C13 C14 . 1.379(3) no
    C13 H13 . 0.9300 no
    C14 C15 . 1.378(3) no
    C14 H14 . 0.9300 no
    C15 C16 . 1.384(2) no
    C15 H15 . 0.9300 no
    C16 H16 . 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
    C10 N1 N2 . . 122.06(13) no
    C10 N1 H1N . . 115.5(13) no
    N2 N1 H1N . . 122.3(13) no
    C9 N2 N1 . . 114.87(13) no
    C8 N3 C1 . . 109.39(12) no
    C8 N3 H3N . . 126.6(14) no
    C1 N3 H3N . . 124.0(14) no
    N3 C1 C2 . . 130.52(14) no
    N3 C1 C6 . . 107.55(13) no
    C2 C1 C6 . . 121.93(15) no
    C3 C2 C1 . . 118.07(14) no
    C3 C2 H2 . . 121.0 no
    C1 C2 H2 . . 121.0 no
    C2 C3 C4 . . 120.22(15) no
    C2 C3 H3 . . 119.9 no
    C4 C3 H3 . . 119.9 no
    C5 C4 C3 . . 122.84(16) no
    C5 C4 Cl1 . . 118.84(12) no
    C3 C4 Cl1 . . 118.32(13) no
    C4 C5 C6 . . 117.68(13) no
    C4 C5 H5 . . 121.2 no
    C6 C5 H5 . . 121.2 no
    C5 C6 C1 . . 119.24(13) no
    C5 C6 C7 . . 134.38(13) no
    C1 C6 C7 . . 106.37(13) no
    C8 C7 C9 . . 125.08(15) no
    C8 C7 C6 . . 106.48(12) no
    C9 C7 C6 . . 128.27(13) no
    N3 C8 C7 . . 110.19(15) no
    N3 C8 H8 . . 124.9 no
    C7 C8 H8 . . 124.9 no
    N2 C9 C7 . . 121.27(14) no
    N2 C9 H9 . . 119.4 no
    C7 C9 H9 . . 119.4 no
    O1 C10 N1 . . 119.16(14) no
    O1 C10 C11 . . 121.38(13) no
    N1 C10 C11 . . 119.45(12) no
    C12 C11 C16 . . 119.64(15) no
    C12 C11 C10 . . 122.50(14) no
    C16 C11 C10 . . 117.86(14) no
    C13 C12 C11 . . 119.94(16) no
    C13 C12 H12 . . 120.0 no
    C11 C12 H12 . . 120.0 no
    C12 C13 C14 . . 120.13(17) no
    C12 C13 H13 . . 119.9 no
    C14 C13 H13 . . 119.9 no
    C15 C14 C13 . . 120.34(16) no
    C15 C14 H14 . . 119.8 no
    C13 C14 H14 . . 119.8 no
    C14 C15 C16 . . 120.00(17) no
    C14 C15 H15 . . 120.0 no
    C16 C15 H15 . . 120.0 no
    C15 C16 C11 . . 119.91(16) no
    C15 C16 H16 . . 120.0 no
    C11 C16 H16 . . 120.0 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 N1 N2 C9 . . . . -168.78(15) no
    C8 N3 C1 C2 . . . . 178.61(16) no
    C8 N3 C1 C6 . . . . -0.70(18) no
    N3 C1 C2 C3 . . . . 179.20(16) no
    C6 C1 C2 C3 . . . . -1.6(2) no
    C1 C2 C3 C4 . . . . 0.3(3) no
    C2 C3 C4 C5 . . . . 1.2(3) no
    C2 C3 C4 Cl1 . . . . -178.90(13) no
    C3 C4 C5 C6 . . . . -1.4(2) no
    Cl1 C4 C5 C6 . . . . 178.69(12) no
    C4 C5 C6 C1 . . . . 0.2(2) no
    C4 C5 C6 C7 . . . . 179.62(16) no
    N3 C1 C6 C5 . . . . -179.26(13) no
    C2 C1 C6 C5 . . . . 1.4(2) no
    N3 C1 C6 C7 . . . . 1.14(16) no
    C2 C1 C6 C7 . . . . -178.25(14) no
    C5 C6 C7 C8 . . . . 179.33(17) no
    C1 C6 C7 C8 . . . . -1.15(17) no
    C5 C6 C7 C9 . . . . -5.2(3) no
    C1 C6 C7 C9 . . . . 174.30(15) no
    C1 N3 C8 C7 . . . . -0.04(19) no
    C9 C7 C8 N3 . . . . -174.89(14) no
    C6 C7 C8 N3 . . . . 0.76(18) no
    N1 N2 C9 C7 . . . . -176.01(14) no
    C8 C7 C9 N2 . . . . 177.16(16) no
    C6 C7 C9 N2 . . . . 2.5(3) no
    N2 N1 C10 O1 . . . . 174.63(14) no
    N2 N1 C10 C11 . . . . -3.6(2) no
    O1 C10 C11 C12 . . . . 132.90(16) no
    N1 C10 C11 C12 . . . . -48.9(2) no
    O1 C10 C11 C16 . . . . -46.5(2) no
    N1 C10 C11 C16 . . . . 131.69(16) no
    C16 C11 C12 C13 . . . . -1.2(2) no
    C10 C11 C12 C13 . . . . 179.35(14) no
    C11 C12 C13 C14 . . . . -0.6(2) no
    C12 C13 C14 C15 . . . . 1.5(3) no
    C13 C14 C15 C16 . . . . -0.7(3) no
    C14 C15 C16 C11 . . . . -1.1(2) no
    C12 C11 C16 C15 . . . . 2.1(2) no
    C10 C11 C16 C15 . . . . -178.50(14) 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 3_776 0.860(10)
                            2.100(10)
                                    2.950(2) 172(2) yes
    N3 H3N O1 4_576 0.860(10)
                            2.060(10)
                                    2.880(2) 159(2) yes
