#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/20/2222042.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_2222042
loop_
_publ_author_name
'Alhadi, Abeer A.'
'Saharin, Siti Munirah'
'Mohd Ali, Hapipah'
'Robinson, Ward T.'
'Abdulla, Mahmood A.'
_publ_section_title
;
 N'-(2,4-Dimethoxybenzylidene)-3,4,5-trihydroxybenzohydrazide
 ethanol solvate
;
_journal_coeditor_code           HG2510
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1373
_journal_paper_doi               10.1107/S1600536809018947
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C16 H16 N2 O6, C2 H6 O'
_chemical_formula_moiety         'C16 H16 N2 O6, C2 H6 O'
_chemical_formula_sum            'C18 H22 N2 O7'
_chemical_formula_weight         378.38
_chemical_name_systematic
;
N'-(2,4-Dimethoxybenzylidene)-3,4,5-trihydroxybenzohydrazide
ethanol solvate
;
_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                 93.9360(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.83470(10)
_cell_length_b                   17.5412(3)
_cell_length_c                   13.0230(2)
_cell_measurement_reflns_used    3445
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.075
_cell_measurement_theta_min      2.802
_cell_volume                     1785.53(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, 2008)'
_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 0.951
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_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  0.0414
_diffrn_reflns_av_sigmaI/netI    0.0440
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            19580
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         30.51
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.9870
_exptl_absorpt_correction_T_min  0.9669
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.265
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         5188
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0444
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0566P)²+0.3538P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1069
_refine_ls_wR_factor_ref         0.1214
_reflns_number_gt                3586
_reflns_number_total             5188
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2510.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.

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.

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               2222042
_cod_database_fobs_code          2222042
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
C C1 1.15941(17) 0.21466(7) 0.76768(10) 0.0156(3) Uani d . 1 . .
H H1 1.1458 0.2583 0.7248 0.019 Uiso calc R 1 . .
C C2 1.25203(17) 0.22016(7) 0.86245(10) 0.0153(3) Uani d . 1 . .
C C3 1.26837(17) 0.15678(8) 0.92716(10) 0.0154(3) Uani d . 1 . .
C C4 1.19696(18) 0.08744(8) 0.89317(10) 0.0170(3) Uani d . 1 . .
C C5 1.10756(18) 0.08150(8) 0.79830(10) 0.0176(3) Uani d . 1 . .
H H5 1.0605 0.0339 0.7760 0.021 Uiso calc R 1 . .
C C6 1.08672(17) 0.14571(7) 0.73529(10) 0.0154(3) Uani d . 1 . .
C C7 0.98683(17) 0.14395(8) 0.63409(10) 0.0159(3) Uani d . 1 . .
C C8 0.74521(17) 0.00842(8) 0.49550(10) 0.0168(3) Uani d . 1 . .
H H8 0.7539 -0.0296 0.5476 0.023(4) Uiso calc R 1 . .
C C9 0.64100(17) -0.00596(8) 0.40063(10) 0.0165(3) Uani d . 1 . .
C C10 0.57036(17) -0.07846(8) 0.38154(10) 0.0163(3) Uani d . 1 . .
C C11 0.47202(17) -0.09404(8) 0.29061(10) 0.0172(3) Uani d . 1 . .
H H11 0.4236 -0.1431 0.2785 0.021 Uiso calc R 1 . .
C C12 0.44633(18) -0.03640(8) 0.21828(11) 0.0188(3) Uani d . 1 . .
C C13 0.51352(19) 0.03637(8) 0.23587(11) 0.0209(3) Uani d . 1 . .
H H13 0.4939 0.0754 0.1859 0.025 Uiso calc R 1 . .
C C14 0.60860(18) 0.05093(8) 0.32640(11) 0.0190(3) Uani d . 1 . .
H H14 0.6533 0.1007 0.3389 0.023 Uiso calc R 1 . .
C C15 0.2879(2) -0.11915(8) 0.09897(11) 0.0227(3) Uani d . 1 . .
H H15A 0.3824 -0.1557 0.0978 0.034 Uiso calc R 1 . .
H H15B 0.2270 -0.1169 0.0307 0.034 Uiso calc R 1 . .
H H15C 0.2087 -0.1354 0.1498 0.034 Uiso calc R 1 . .
C C16 0.5321(2) -0.20516(8) 0.44383(12) 0.0247(3) Uani d . 1 . .
H H16A 0.4072 -0.2007 0.4358 0.037 Uiso calc R 1 . .
H H16B 0.5647 -0.2364 0.5044 0.037 Uiso calc R 1 . .
H H16C 0.5737 -0.2292 0.3824 0.037 Uiso calc R 1 . .
C C17 0.7901(2) 0.81507(9) 0.72385(14) 0.0313(4) Uani d . 1 . .
H H19A 0.6929 0.8370 0.6826 0.047 Uiso calc R 1 . .
H H19B 0.7482 0.7866 0.7818 0.047 Uiso calc R 1 . .
H H19C 0.8531 0.7806 0.6809 0.047 Uiso calc R 1 . .
C C18 0.9073(2) 0.87827(9) 0.76416(12) 0.0259(3) Uani d . 1 . .
H H18A 0.8458 0.9110 0.8113 0.031 Uiso calc R 1 . .
H H18B 1.0074 0.8559 0.8038 0.031 Uiso calc R 1 . .
N N1 0.92094(15) 0.07647(6) 0.60343(9) 0.0168(2) Uani d . 1 . .
H H1' 0.9379 0.0357 0.6422 0.030(5) Uiso calc R 1 . .
N N2 0.82556(15) 0.07168(6) 0.50974(9) 0.0174(2) Uani d . 1 . .
O O1 0.96209(13) 0.20261(5) 0.58110(7) 0.0219(2) Uani d . 1 . .
O O2 1.32670(14) 0.28879(5) 0.88620(7) 0.0218(2) Uani d . 1 . .
H H2 1.3569 0.2901 0.9493 0.033 Uiso calc R 1 . .
O O3 1.35316(13) 0.15568(6) 1.02261(7) 0.0209(2) Uani d . 1 . .
H H3 1.3877 0.1998 1.0381 0.031 Uiso calc R 1 . .
O O4 1.21299(15) 0.02350(6) 0.95174(8) 0.0273(3) Uani d . 1 . .
H H4 1.2718 0.0332 1.0065 0.041 Uiso calc R 1 . .
O O5 0.60584(13) -0.13118(6) 0.45673(7) 0.0224(2) Uani d . 1 . .
O O6 0.35424(14) -0.04532(6) 0.12604(8) 0.0264(3) Uani d . 1 . .
O O7 0.96498(14) 0.92367(6) 0.68270(8) 0.0229(2) Uani d . 1 . .
H H7 1.0291 0.8975 0.6475 0.034 Uiso calc R 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'
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
C6 C1 C2 . . 120.50(12) ?
C6 C1 H1 . . 119.8 ?
C2 C1 H1 . . 119.8 ?
O2 C2 C1 . . 116.85(12) ?
O2 C2 C3 . . 123.07(11) ?
C1 C2 C3 . . 120.06(12) ?
O3 C3 C2 . . 125.32(12) ?
O3 C3 C4 . . 115.73(11) ?
C2 C3 C4 . . 118.93(11) ?
O4 C4 C5 . . 117.51(12) ?
O4 C4 C3 . . 121.43(12) ?
C5 C4 C3 . . 121.07(12) ?
C4 C5 C6 . . 119.75(12) ?
C4 C5 H5 . . 120.1 ?
C6 C5 H5 . . 120.1 ?
C1 C6 C5 . . 119.63(12) ?
C1 C6 C7 . . 117.84(11) ?
C5 C6 C7 . . 122.52(12) ?
O1 C7 N1 . . 121.44(12) ?
O1 C7 C6 . . 121.75(12) ?
N1 C7 C6 . . 116.79(12) ?
N2 C8 C9 . . 120.91(12) ?
N2 C8 H8 . . 119.5 ?
C9 C8 H8 . . 119.5 ?
C14 C9 C10 . . 118.24(12) ?
C14 C9 C8 . . 121.81(12) ?
C10 C9 C8 . . 119.95(12) ?
O5 C10 C11 . . 123.45(12) ?
O5 C10 C9 . . 115.45(11) ?
C11 C10 C9 . . 121.09(12) ?
C12 C11 C10 . . 118.67(12) ?
C12 C11 H11 . . 120.7 ?
C10 C11 H11 . . 120.7 ?
O6 C12 C11 . . 123.82(12) ?
O6 C12 C13 . . 114.82(12) ?
C11 C12 C13 . . 121.36(12) ?
C14 C13 C12 . . 119.17(13) ?
C14 C13 H13 . . 120.4 ?
C12 C13 H13 . . 120.4 ?
C13 C14 C9 . . 121.44(13) ?
C13 C14 H14 . . 119.3 ?
C9 C14 H14 . . 119.3 ?
O6 C15 H15A . . 109.5 ?
O6 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
O6 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
O5 C16 H16A . . 109.5 ?
O5 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
O5 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C18 C17 H19A . . 109.5 ?
C18 C17 H19B . . 109.5 ?
H19A C17 H19B . . 109.5 ?
C18 C17 H19C . . 109.5 ?
H19A C17 H19C . . 109.5 ?
H19B C17 H19C . . 109.5 ?
O7 C18 C17 . . 111.58(13) ?
O7 C18 H18A . . 109.3 ?
C17 C18 H18A . . 109.3 ?
O7 C18 H18B . . 109.3 ?
C17 C18 H18B . . 109.3 ?
H18A C18 H18B . . 108.0 ?
C7 N1 N2 . . 119.19(11) ?
C7 N1 H1' . . 120.4 ?
N2 N1 H1' . . 120.4 ?
C8 N2 N1 . . 114.10(11) ?
C2 O2 H2 . . 109.5 ?
C3 O3 H3 . . 109.5 ?
C4 O4 H4 . . 109.5 ?
C10 O5 C16 . . 118.18(11) ?
C12 O6 C15 . . 118.75(11) ?
C18 O7 H7 . . 109.5 ?
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
C1 C6 . 1.3900(18) ?
C1 C2 . 1.3914(18) ?
C1 H1 . 0.9500 ?
C2 O2 . 1.3647(15) ?
C2 C3 . 1.3958(18) ?
C3 O3 . 1.3687(15) ?
C3 C4 . 1.3979(18) ?
C4 O4 . 1.3574(16) ?
C4 C5 . 1.3818(18) ?
C5 C6 . 1.3965(18) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.4862(18) ?
C7 O1 . 1.2466(16) ?
C7 N1 . 1.3412(17) ?
C8 N2 . 1.2830(17) ?
C8 C9 . 1.4554(18) ?
C8 H8 . 0.9500 ?
C9 C14 . 1.4004(19) ?
C9 C10 . 1.4023(18) ?
C10 O5 . 1.3615(16) ?
C10 C11 . 1.3948(18) ?
C11 C12 . 1.3869(19) ?
C11 H11 . 0.9500 ?
C12 O6 . 1.3672(16) ?
C12 C13 . 1.3938(19) ?
C13 C14 . 1.3745(19) ?
C13 H13 . 0.9500 ?
C14 H14 . 0.9500 ?
C15 O6 . 1.4308(16) ?
C15 H15A . 0.9800 ?
C15 H15B . 0.9800 ?
C15 H15C . 0.9800 ?
C16 O5 . 1.4258(17) ?
C16 H16A . 0.9800 ?
C16 H16B . 0.9800 ?
C16 H16C . 0.9800 ?
C17 C18 . 1.511(2) ?
C17 H19A . 0.9800 ?
C17 H19B . 0.9800 ?
C17 H19C . 0.9800 ?
C18 O7 . 1.4247(18) ?
C18 H18A . 0.9900 ?
C18 H18B . 0.9900 ?
N1 N2 . 1.3889(15) ?
N1 H1' . 0.8800 ?
O2 H2 . 0.8400 ?
O3 H3 . 0.8400 ?
O4 H4 . 0.8400 ?
O7 H7 . 0.8400 ?
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
O2 H2 O3 . 0.84 2.54 2.9325(13) 109.4
O3 H3 O2 . 0.84 2.54 2.9325(13) 109.8
O4 H4 O3 . 0.84 2.25 2.7009(14) 114.2
N1 H1' O7 1_545 0.88 2.04 2.8844(15) 160
O2 H2 O1 4_666 0.84 1.86 2.6871(13) 169.7
O2 H2 N2 4_666 0.84 2.57 2.9293(15) 107.4
O3 H3 O1 4_666 0.84 1.88 2.7200(13) 176.5
O4 H4 O6 1_656 0.84 2.14 2.7366(14) 127.3
C14 H14 O2 4_565 0.95 2.42 3.3539(17) 166.5
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655789
