#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/06/2220665.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2220665
loop_
_publ_author_name
'Khaledi, Hamid'
'Mohd Ali, Hapipah'
'Ng, Seik Weng'
_publ_section_title
N'-[(5-Chloro-1H-indol-3-yl)methylene]-3,4,5-trihydroxybenzohydrazide
_journal_coeditor_code           XU2471
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o169
_journal_paper_doi               10.1107/S160053680804258X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C16 H12 Cl N3 O4'
_chemical_formula_moiety         'C16 H12 Cl N3 O4'
_chemical_formula_sum            'C16 H12 Cl N3 O4'
_chemical_formula_weight         345.74
_chemical_name_common
;
5-Chloro-1H-indole-3-carbaldehyde 3,4,5-trihydroxyphenylhydrazone
;
_chemical_name_systematic
;
N'-[(5-Chloro-1H-indol-3-yl)methylene]-3,4,5-\
trihydroxybenzohydrazide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.2320(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6481(2)
_cell_length_b                   15.1408(3)
_cell_length_c                   10.2206(2)
_cell_measurement_reflns_used    4113
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.2
_cell_measurement_theta_min      2.4
_cell_volume                     1477.64(5)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'X-SEED (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10185
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.42
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.286
_exptl_absorpt_correction_T_max  0.9664
_exptl_absorpt_correction_T_min  0.9139
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.329
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3389
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0341
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0452P)²+0.6635P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0885
_refine_ls_wR_factor_ref         0.0926
_reflns_number_gt                2907
_reflns_number_total             3389
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2471.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed
to 'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2220665
_cod_database_fobs_code          2220665
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'
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 0.99034(4) 1.07558(3) 0.24671(4) 0.02606(12) Uani d . 1 . .
O O1 0.68592(10) 0.82901(7) 0.56884(10) 0.0165(2) Uani d . 1 . .
O O2 0.64086(10) 0.62519(7) 0.94667(10) 0.0172(2) Uani d . 1 . .
H H2O 0.5962 0.5961 0.9968 0.026 Uiso calc R 1 . .
O O3 0.36728(11) 0.59550(6) 0.94304(9) 0.0140(2) Uani d . 1 . .
H H3O 0.3047 0.6195 0.9801 0.021 Uiso calc R 1 . .
O O4 0.16964(10) 0.67781(7) 0.73963(10) 0.0149(2) Uani d . 1 . .
H H4O 0.1521 0.6414 0.7971 0.022 Uiso calc R 1 . .
N N1 0.46397(12) 0.86816(8) 0.48430(11) 0.0138(2) Uani d . 1 . .
H H1N 0.3740 0.8638 0.4895 0.017 Uiso calc R 1 . .
N N2 0.51003(13) 0.92205(7) 0.38882(11) 0.0137(2) Uani d . 1 . .
N N3 0.39990(13) 1.10793(8) 0.03144(12) 0.0162(3) Uani d . 1 . .
H H3N 0.3544 1.1361 -0.0369 0.019 Uiso calc R 1 . .
C C1 0.50119(15) 0.76183(9) 0.66318(13) 0.0130(3) Uani d . 1 . .
C C2 0.59758(15) 0.72084(9) 0.75913(13) 0.0141(3) Uani d . 1 . .
H H2 0.6952 0.7305 0.7616 0.017 Uiso calc R 1 . .
C C3 0.54846(15) 0.66576(9) 0.85061(13) 0.0131(3) Uani d . 1 . .
C C4 0.40551(15) 0.65121(9) 0.84928(13) 0.0123(3) Uani d . 1 . .
C C5 0.31087(14) 0.69082(9) 0.75114(13) 0.0125(3) Uani d . 1 . .
C C6 0.35827(15) 0.74599(9) 0.65851(13) 0.0133(3) Uani d . 1 . .
H H6 0.2932 0.7730 0.5919 0.016 Uiso calc R 1 . .
C C7 0.55811(15) 0.82260(9) 0.56894(13) 0.0131(3) Uani d . 1 . .
C C8 0.41317(15) 0.96681(9) 0.31823(13) 0.0142(3) Uani d . 1 . .
H H8 0.3195 0.9615 0.3358 0.017 Uiso calc R 1 . .
C C9 0.44207(15) 1.02444(9) 0.21398(13) 0.0142(3) Uani d . 1 . .
C C10 0.33977(16) 1.05950(9) 0.11972(14) 0.0162(3) Uani d . 1 . .
H H10 0.2419 1.0509 0.1172 0.019 Uiso calc R 1 . .
C C11 0.57451(15) 1.05429(9) 0.18016(13) 0.0133(3) Uani d . 1 . .
C C12 0.71420(15) 1.04422(9) 0.23767(13) 0.0147(3) Uani d . 1 . .
H H12 0.7386 1.0109 0.3164 0.018 Uiso calc R 1 . .
C C13 0.81494(16) 1.08455(10) 0.17549(14) 0.0169(3) Uani d . 1 . .
C C14 0.78385(16) 1.13505(10) 0.06023(14) 0.0187(3) Uani d . 1 . .
H H14 0.8574 1.1609 0.0206 0.022 Uiso calc R 1 . .
C C15 0.64682(16) 1.14724(9) 0.00445(14) 0.0172(3) Uani d . 1 . .
H H15 0.6235 1.1823 -0.0727 0.021 Uiso calc R 1 . .
C C16 0.54321(16) 1.10616(9) 0.06539(13) 0.0146(3) Uani d . 1 . .
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'
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
C3 O2 H2O . . 109.5 ?
C4 O3 H3O . . 109.5 ?
C5 O4 H4O . . 109.5 ?
C7 N1 N2 . . 119.69(12) ?
C7 N1 H1N . . 120.2 ?
N2 N1 H1N . . 120.2 ?
C8 N2 N1 . . 114.96(12) ?
C10 N3 C16 . . 109.38(12) ?
C10 N3 H3N . . 125.3 ?
C16 N3 H3N . . 125.3 ?
C6 C1 C2 . . 120.24(13) ?
C6 C1 C7 . . 122.53(13) ?
C2 C1 C7 . . 117.23(13) ?
C3 C2 C1 . . 118.90(13) ?
C3 C2 H2 . . 120.5 ?
C1 C2 H2 . . 120.5 ?
O2 C3 C2 . . 120.11(12) ?
O2 C3 C4 . . 118.44(12) ?
C2 C3 C4 . . 121.44(13) ?
O3 C4 C5 . . 123.80(13) ?
O3 C4 C3 . . 117.16(12) ?
C5 C4 C3 . . 118.99(12) ?
O4 C5 C6 . . 116.76(12) ?
O4 C5 C4 . . 122.94(12) ?
C6 C5 C4 . . 120.30(13) ?
C5 C6 C1 . . 120.07(13) ?
C5 C6 H6 . . 120.0 ?
C1 C6 H6 . . 120.0 ?
O1 C7 N1 . . 122.58(13) ?
O1 C7 C1 . . 120.52(13) ?
N1 C7 C1 . . 116.90(12) ?
N2 C8 C9 . . 122.22(13) ?
N2 C8 H8 . . 118.9 ?
C9 C8 H8 . . 118.9 ?
C10 C9 C8 . . 123.75(14) ?
C10 C9 C11 . . 106.32(12) ?
C8 C9 C11 . . 129.87(13) ?
N3 C10 C9 . . 109.91(13) ?
N3 C10 H10 . . 125.0 ?
C9 C10 H10 . . 125.0 ?
C12 C11 C16 . . 119.31(13) ?
C12 C11 C9 . . 134.24(13) ?
C16 C11 C9 . . 106.41(13) ?
C13 C12 C11 . . 117.29(13) ?
C13 C12 H12 . . 121.4 ?
C11 C12 H12 . . 121.4 ?
C12 C13 C14 . . 123.35(14) ?
C12 C13 Cl1 . . 118.55(11) ?
C14 C13 Cl1 . . 118.07(11) ?
C15 C14 C13 . . 119.96(14) ?
C15 C14 H14 . . 120.0 ?
C13 C14 H14 . . 120.0 ?
C14 C15 C16 . . 117.53(13) ?
C14 C15 H15 . . 121.2 ?
C16 C15 H15 . . 121.2 ?
N3 C16 C15 . . 129.48(13) ?
N3 C16 C11 . . 107.98(12) ?
C15 C16 C11 . . 122.54(14) ?
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 C13 . 1.7491(15) ?
O1 C7 . 1.2371(17) ?
O2 C3 . 1.3731(16) ?
O2 H2O . 0.8400 ?
O3 C4 . 1.3664(16) ?
O3 H3O . 0.8400 ?
O4 C5 . 1.3650(16) ?
O4 H4O . 0.8400 ?
N1 C7 . 1.3506(18) ?
N1 N2 . 1.3927(16) ?
N1 H1N . 0.8800 ?
N2 C8 . 1.2884(19) ?
N3 C10 . 1.3558(19) ?
N3 C16 . 1.3768(19) ?
N3 H3N . 0.8800 ?
C1 C6 . 1.3936(19) ?
C1 C2 . 1.397(2) ?
C1 C7 . 1.4925(19) ?
C2 C3 . 1.3860(19) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.3948(19) ?
C4 C5 . 1.3919(19) ?
C5 C6 . 1.3883(19) ?
C6 H6 . 0.9500 ?
C8 C9 . 1.4350(19) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.383(2) ?
C9 C11 . 1.443(2) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.399(2) ?
C11 C16 . 1.4080(19) ?
C12 C13 . 1.378(2) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.400(2) ?
C14 C15 . 1.375(2) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.397(2) ?
C15 H15 . 0.9500 ?
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 H2o O3 . 0.84 2.20 2.6726(14) 116 yes
O3 H3o O1 4_576 0.84 1.74 2.5818(14) 175 yes
O4 H4o N2 4_576 0.84 2.01 2.7668(15) 149 yes
N1 H1n O2 4_575 0.88 2.23 3.0875(16) 163 yes
N3 H3n O4 2 0.88 2.15 2.9518(15) 152 yes
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
C7 N1 N2 C8 . . . . -175.96(12) ?
C6 C1 C2 C3 . . . . -1.2(2) ?
C7 C1 C2 C3 . . . . 178.31(12) ?
C1 C2 C3 O2 . . . . -179.47(12) ?
C1 C2 C3 C4 . . . . -0.5(2) ?
O2 C3 C4 O3 . . . . -1.36(18) ?
C2 C3 C4 O3 . . . . 179.69(12) ?
O2 C3 C4 C5 . . . . -178.98(12) ?
C2 C3 C4 C5 . . . . 2.1(2) ?
O3 C4 C5 O4 . . . . 0.2(2) ?
C3 C4 C5 O4 . . . . 177.70(12) ?
O3 C4 C5 C6 . . . . -179.32(12) ?
C3 C4 C5 C6 . . . . -1.9(2) ?
O4 C5 C6 C1 . . . . -179.44(12) ?
C4 C5 C6 C1 . . . . 0.2(2) ?
C2 C1 C6 C5 . . . . 1.4(2) ?
C7 C1 C6 C5 . . . . -178.09(12) ?
N2 N1 C7 O1 . . . . 2.73(19) ?
N2 N1 C7 C1 . . . . -176.29(11) ?
C6 C1 C7 O1 . . . . -173.65(13) ?
C2 C1 C7 O1 . . . . 6.83(19) ?
C6 C1 C7 N1 . . . . 5.39(19) ?
C2 C1 C7 N1 . . . . -174.13(12) ?
N1 N2 C8 C9 . . . . -178.92(12) ?
N2 C8 C9 C10 . . . . 166.52(13) ?
N2 C8 C9 C11 . . . . -10.3(2) ?
C16 N3 C10 C9 . . . . -0.12(16) ?
C8 C9 C10 N3 . . . . -177.25(12) ?
C11 C9 C10 N3 . . . . 0.18(15) ?
C10 C9 C11 C12 . . . . 177.59(15) ?
C8 C9 C11 C12 . . . . -5.2(3) ?
C10 C9 C11 C16 . . . . -0.17(15) ?
C8 C9 C11 C16 . . . . 177.04(14) ?
C16 C11 C12 C13 . . . . -1.65(19) ?
C9 C11 C12 C13 . . . . -179.19(14) ?
C11 C12 C13 C14 . . . . 0.7(2) ?
C11 C12 C13 Cl1 . . . . 178.50(10) ?
C12 C13 C14 C15 . . . . 0.8(2) ?
Cl1 C13 C14 C15 . . . . -176.97(11) ?
C13 C14 C15 C16 . . . . -1.3(2) ?
C10 N3 C16 C15 . . . . -179.12(14) ?
C10 N3 C16 C11 . . . . 0.00(15) ?
C14 C15 C16 N3 . . . . 179.40(14) ?
C14 C15 C16 C11 . . . . 0.4(2) ?
C12 C11 C16 N3 . . . . -178.05(12) ?
C9 C11 C16 N3 . . . . 0.11(15) ?
C12 C11 C16 C15 . . . . 1.1(2) ?
C9 C11 C16 C15 . . . . 179.30(13) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655701
