#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/38/2223824.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_2223824
loop_
_publ_author_name
'Zukerman-Schpector, Julio'
'Affan, Md. Abu'
'Foo, Siong Wan'
'Tiekink, Edward R. T.'
_publ_section_title
;
 1,5-Bis[(E)-1-(2-hydroxyphenyl)ethylidene]carbonohydrazide
 dimethyl sulfoxide solvate
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2951
_journal_paper_doi               10.1107/S1600536809044985
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C17 H18 N4 O3, C2 H6 O S'
_chemical_formula_moiety         'C17 H18 N4 O3, C2 H6 O S'
_chemical_formula_sum            'C19 H24 N4 O4 S'
_chemical_formula_weight         404.48
_chemical_name_systematic
;
1,5-Bis[(E)-1-(2-hydroxyphenyl)ethylidene]carbonohydrazide
dimethyl sulfoxide solvate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 102.724(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.3260(19)
_cell_length_b                   7.1248(7)
_cell_length_c                   18.439(2)
_cell_measurement_reflns_used    6256
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      30.3
_cell_measurement_theta_min      2.7
_cell_volume                     1964.0(4)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2005)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
;
Rigaku Saturn724
;
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.030
_diffrn_reflns_av_sigmaI/netI    0.022
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            21771
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         2.3
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.661
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.32
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         4493
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0408
_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)+(0.0572P)²+0.8148P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1092
_refine_ls_wR_factor_ref         0.1102
_reflns_number_gt                4369
_reflns_number_total             4493
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5198.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_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:

'_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/c'
_cod_database_code               2223824
_cod_database_fobs_code          2223824
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'
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 0.31503(7) -0.00388(17) 0.72741(5) 0.0315(2) Uani d D 1 . .
H H1O 0.2776 0.0352 0.6901 0.047 Uiso d D 1 . .
O O2 0.08573(6) 0.17694(15) 0.63438(5) 0.0258(2) Uani d . 1 . .
O O3 -0.14836(6) 0.29124(14) 0.62863(5) 0.0248(2) Uani d D 1 . .
H H3O -0.1046 0.27566 0.6087 0.037 Uiso d D 1 . .
N N1 0.24627(7) 0.12659(16) 0.59756(6) 0.0207(2) Uani d . 1 . .
N N2 0.17027(7) 0.17151(17) 0.54592(6) 0.0221(2) Uani d D 1 . .
H H2N 0.1683 0.1867 0.4982 0.026 Uiso d D 1 . .
N N3 0.02270(7) 0.24035(16) 0.51181(6) 0.0221(2) Uani d D 1 . .
H H3N 0.0339 0.2475 0.4671 0.027 Uiso d D 1 . .
N N4 -0.05924(7) 0.26766(15) 0.52770(6) 0.0204(2) Uani d . 1 . .
C C1 0.39368(9) 0.00078(19) 0.70500(8) 0.0233(3) Uani d . 1 . .
C C2 0.47033(10) -0.0498(2) 0.75744(8) 0.0289(3) Uani d . 1 . .
H H2 0.4655 -0.0855 0.8060 0.035 Uiso calc R 1 . .
C C3 0.55316(10) -0.0486(2) 0.73960(9) 0.0306(3) Uani d . 1 . .
H H3 0.6050 -0.0826 0.7759 0.037 Uiso calc R 1 . .
C C4 0.56065(9) 0.0023(2) 0.66867(9) 0.0304(3) Uani d . 1 . .
H H4 0.6176 0.0036 0.6562 0.037 Uiso calc R 1 . .
C C5 0.48487(9) 0.0513(2) 0.61617(8) 0.0259(3) Uani d . 1 . .
H H5 0.4907 0.0848 0.5676 0.031 Uiso calc R 1 . .
C C6 0.39962(8) 0.05313(17) 0.63249(7) 0.0200(2) Uani d . 1 . .
C C7 0.31992(8) 0.10518(17) 0.57510(7) 0.0195(2) Uani d . 1 . .
C C8 0.32461(9) 0.1268(2) 0.49519(7) 0.0256(3) Uani d . 1 . .
H H8A 0.2859 0.0332 0.4651 0.038 Uiso calc R 1 . .
H H8B 0.3864 0.1082 0.4903 0.038 Uiso calc R 1 . .
H H8C 0.3046 0.2530 0.4780 0.038 Uiso calc R 1 . .
C C9 0.09245(8) 0.19450(18) 0.56997(7) 0.0202(3) Uani d . 1 . .
C C10 -0.12715(8) 0.30637(18) 0.47447(7) 0.0199(3) Uani d . 1 . .
C C11 -0.12059(9) 0.3222(2) 0.39461(7) 0.0278(3) Uani d . 1 . .
H H11A -0.0659 0.3903 0.3917 0.042 Uiso calc R 1 . .
H H11B -0.1727 0.3904 0.3665 0.042 Uiso calc R 1 . .
H H11C -0.1189 0.1964 0.3735 0.042 Uiso calc R 1 . .
C C12 -0.21323(8) 0.33360(17) 0.49676(7) 0.0193(2) Uani d . 1 . .
C C13 -0.21935(9) 0.32848(18) 0.57248(7) 0.0213(3) Uani d . 1 . .
C C14 -0.30117(9) 0.36037(19) 0.59185(8) 0.0253(3) Uani d . 1 . .
H H14 -0.3042 0.3618 0.6428 0.030 Uiso calc R 1 . .
C C15 -0.37788(9) 0.3899(2) 0.53742(9) 0.0282(3) Uani d . 1 . .
H H15 -0.4333 0.4109 0.5512 0.034 Uiso calc R 1 . .
C C16 -0.37441(9) 0.3891(2) 0.46264(8) 0.0277(3) Uani d . 1 . .
H H16 -0.4274 0.4061 0.4253 0.033 Uiso calc R 1 . .
C C17 -0.29285(9) 0.36309(19) 0.44331(8) 0.0240(3) Uani d . 1 . .
H H17 -0.2907 0.3653 0.3922 0.029 Uiso calc R 1 . .
S S1 0.88984(2) 0.73077(5) 0.686182(17) 0.02070(11) Uani d . 1 . .
O O4 0.88705(7) 0.75110(16) 0.60411(5) 0.0286(2) Uani d . 1 . .
C C18 0.79058(9) 0.8403(2) 0.70127(8) 0.0286(3) Uani d . 1 . .
H H18A 0.7859 0.9673 0.6804 0.043 Uiso calc R 1 . .
H H18B 0.7930 0.8470 0.7548 0.043 Uiso calc R 1 . .
H H18C 0.7383 0.7666 0.6769 0.043 Uiso calc R 1 . .
C C19 0.96707(9) 0.9044(2) 0.73080(7) 0.0258(3) Uani d . 1 . .
H H19A 1.0273 0.8722 0.7250 0.039 Uiso calc R 1 . .
H H19B 0.9664 0.9093 0.7838 0.039 Uiso calc R 1 . .
H H19C 0.9499 1.0271 0.7081 0.039 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'
S S 0.1246 0.1234 '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
C1 O1 H1O . . 103.5 ?
C13 O3 H3O . . 106.0 ?
C7 N1 N2 . . 118.23(11) ?
N1 N2 C9 . . 118.05(10) ?
N1 N2 H2N . . 124.1 ?
C9 N2 H2N . . 117.9 ?
N4 N3 C9 . . 117.39(11) ?
N4 N3 H3N . . 124.8 ?
C9 N3 H3N . . 117.7 ?
C10 N4 N3 . . 119.49(11) ?
O1 C1 C2 . . 116.83(12) ?
O1 C1 C6 . . 122.81(11) ?
C2 C1 C6 . . 120.35(12) ?
C3 C2 C1 . . 120.79(13) ?
C3 C2 H2 . . 119.6 ?
C1 C2 H2 . . 119.6 ?
C2 C3 C4 . . 119.89(13) ?
C2 C3 H3 . . 120.1 ?
C4 C3 H3 . . 120.1 ?
C5 C4 C3 . . 119.68(13) ?
C5 C4 H4 . . 120.2 ?
C3 C4 H4 . . 120.2 ?
C4 C5 C6 . . 122.01(13) ?
C4 C5 H5 . . 119.0 ?
C6 C5 H5 . . 119.0 ?
C5 C6 C1 . . 117.27(12) ?
C5 C6 C7 . . 120.72(12) ?
C1 C6 C7 . . 122.01(11) ?
N1 C7 C6 . . 116.26(11) ?
N1 C7 C8 . . 122.45(11) ?
C6 C7 C8 . . 121.28(11) ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
O2 C9 N2 . . 124.62(12) ?
O2 C9 N3 . . 124.39(12) ?
N2 C9 N3 . . 110.99(11) ?
N4 C10 C12 . . 115.80(11) ?
N4 C10 C11 . . 122.93(11) ?
C12 C10 C11 . . 121.27(11) ?
C10 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C10 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C17 C12 C13 . . 117.26(11) ?
C17 C12 C10 . . 120.98(11) ?
C13 C12 C10 . . 121.75(11) ?
O3 C13 C14 . . 116.90(12) ?
O3 C13 C12 . . 122.77(11) ?
C14 C13 C12 . . 120.33(12) ?
C15 C14 C13 . . 120.45(13) ?
C15 C14 H14 . . 119.8 ?
C13 C14 H14 . . 119.8 ?
C14 C15 C16 . . 120.42(12) ?
C14 C15 H15 . . 119.8 ?
C16 C15 H15 . . 119.8 ?
C17 C16 C15 . . 119.28(13) ?
C17 C16 H16 . . 120.4 ?
C15 C16 H16 . . 120.4 ?
C16 C17 C12 . . 122.19(12) ?
C16 C17 H17 . . 118.9 ?
C12 C17 H17 . . 118.9 ?
O4 S1 C19 . . 105.37(6) ?
O4 S1 C18 . . 106.08(6) ?
C19 S1 C18 . . 97.28(7) ?
S1 C18 H18A . . 109.5 ?
S1 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
S1 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
S1 C19 H19A . . 109.5 ?
S1 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
S1 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 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
O1 C1 . 1.3580(16) ?
O1 H1O . 0.8401 ?
O2 C9 . 1.2210(16) ?
O3 C13 . 1.3528(16) ?
O3 H3O . 0.8400 ?
N1 C7 . 1.2942(16) ?
N1 N2 . 1.3700(15) ?
N2 C9 . 1.3707(16) ?
N2 H2N . 0.8799 ?
N3 N4 . 1.3648(15) ?
N3 C9 . 1.3764(17) ?
N3 H3N . 0.8799 ?
N4 C10 . 1.2933(17) ?
C1 C2 . 1.3944(19) ?
C1 C6 . 1.4103(18) ?
C2 C3 . 1.380(2) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.386(2) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.383(2) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.4039(18) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.4765(17) ?
C7 C8 . 1.4987(17) ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
C10 C12 . 1.4785(17) ?
C10 C11 . 1.5021(17) ?
C11 H11A . 0.9800 ?
C11 H11B . 0.9800 ?
C11 H11C . 0.9800 ?
C12 C17 . 1.4053(18) ?
C12 C13 . 1.4202(17) ?
C13 C14 . 1.3961(18) ?
C14 C15 . 1.383(2) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.392(2) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.3856(19) ?
C16 H16 . 0.9500 ?
C17 H17 . 0.9500 ?
S1 O4 . 1.5115(10) ?
S1 C19 . 1.7830(14) ?
S1 C18 . 1.7852(14) ?
C18 H18A . 0.9800 ?
C18 H18B . 0.9800 ?
C18 H18C . 0.9800 ?
C19 H19A . 0.9800 ?
C19 H19B . 0.9800 ?
C19 H19C . 0.9800 ?
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 1_555 0.84 1.79 2.5682(15) 153 y
O3 H3o N4 1_555 0.84 1.78 2.5450(15) 150 y
N2 H2n O4 3_666 0.88 1.94 2.7674(15) 156 y
N3 H3n O4 3_666 0.88 1.97 2.7907(15) 154 y
C19 H19b O2 2_656 0.98 2.49 3.2167(17) 131 y
C8 H8A Cg2 3_556 0.98 2.83 3.5018(16) 127 y
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 C9 . . . . -179.85(12) ?
C9 N3 N4 C10 . . . . -178.29(11) ?
O1 C1 C2 C3 . . . . -179.82(13) ?
C6 C1 C2 C3 . . . . 0.3(2) ?
C1 C2 C3 C4 . . . . -0.4(2) ?
C2 C3 C4 C5 . . . . -0.1(2) ?
C3 C4 C5 C6 . . . . 0.6(2) ?
C4 C5 C6 C1 . . . . -0.6(2) ?
C4 C5 C6 C7 . . . . -179.69(13) ?
O1 C1 C6 C5 . . . . -179.69(13) ?
C2 C1 C6 C5 . . . . 0.1(2) ?
O1 C1 C6 C7 . . . . -0.6(2) ?
C2 C1 C6 C7 . . . . 179.18(12) ?
N2 N1 C7 C6 . . . . -178.82(11) ?
N2 N1 C7 C8 . . . . -0.32(19) ?
C5 C6 C7 N1 . . . . -171.33(12) ?
C1 C6 C7 N1 . . . . 9.66(18) ?
C5 C6 C7 C8 . . . . 10.15(19) ?
C1 C6 C7 C8 . . . . -168.86(12) ?
N1 N2 C9 O2 . . . . -0.4(2) ?
N1 N2 C9 N3 . . . . 179.57(11) ?
N4 N3 C9 O2 . . . . 0.0(2) ?
N4 N3 C9 N2 . . . . -179.96(11) ?
N3 N4 C10 C12 . . . . 179.97(11) ?
N3 N4 C10 C11 . . . . 0.31(19) ?
N4 C10 C12 C17 . . . . -175.46(12) ?
C11 C10 C12 C17 . . . . 4.20(19) ?
N4 C10 C12 C13 . . . . 3.63(18) ?
C11 C10 C12 C13 . . . . -176.71(12) ?
C17 C12 C13 O3 . . . . 176.40(12) ?
C10 C12 C13 O3 . . . . -2.72(19) ?
C17 C12 C13 C14 . . . . -2.83(18) ?
C10 C12 C13 C14 . . . . 178.05(12) ?
O3 C13 C14 C15 . . . . -176.70(12) ?
C12 C13 C14 C15 . . . . 2.6(2) ?
C13 C14 C15 C16 . . . . -0.3(2) ?
C14 C15 C16 C17 . . . . -1.7(2) ?
C15 C16 C17 C12 . . . . 1.3(2) ?
C13 C12 C17 C16 . . . . 0.9(2) ?
C10 C12 C17 C16 . . . . -179.98(12) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655920
