#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/25/2202559.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_2202559
loop_
_publ_author_name
'Hapipah Ali'
'Zuraina Kadir'
'M. Sukeri M. Yusof'
'Bohari M. Yamin'
_publ_section_title
Bis{μ-N-[1-(2-oxidophenyl)ethylidene]benzohydrazido}bis[(dimethylsulfoxide)zinc(II)]
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m655
_journal_page_last               m657
_journal_paper_doi               10.1107/S1600536803016118
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          '[Zn2 (C15 H12 N2 O2)2 (C2 H6 O S)2]'
_chemical_formula_moiety         'C34 H36 N4 O6 S2 Zn2'
_chemical_formula_sum            'C34 H36 N4 O6 S2 Zn2'
_chemical_formula_weight         791.53
_chemical_name_systematic
;
Bis{μ-N-[1-(2-
oxidophenyl)ethylidene]benzohydrazido}bis[(dimethylsulfoxido)zinc(II)]
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                98.479(13)
_cell_angle_beta                 94.262(12)
_cell_angle_gamma                110.338(13)
_cell_formula_units_Z            1
_cell_length_a                   7.690(4)
_cell_length_b                   10.214(6)
_cell_length_c                   11.643(6)
_cell_measurement_reflns_used    8764
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.7
_cell_volume                     840.3(8)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material
;
SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 1997)'
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 83.66
_diffrn_measured_fraction_theta_full 0.97
_diffrn_measured_fraction_theta_max 0.97
_diffrn_measurement_device_type
;
Bruker SMART APEX 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  0.019
_diffrn_reflns_av_sigmaI/netI    0.019
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10556
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         1.7
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.603
_exptl_absorpt_correction_T_max  0.588
_exptl_absorpt_correction_T_min  0.454
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.31
_refine_ls_extinction_coef       0.0148(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.10
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3804
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.10
_refine_ls_R_factor_all          0.025
_refine_ls_R_factor_gt           0.024
_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)+(0.0374P)²+0.2073P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.067
_refine_ls_wR_factor_ref         0.068
_reflns_number_gt                3653
_reflns_number_total             3804
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv6208.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 'Triclinic' changed to 'triclinic'
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_database_code               2202559
_cod_database_fobs_code          2202559
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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
_atom_site_type_symbol
Zn1 0.14613(2) 0.136649(15) 0.580740(13) 0.03043(8) Uani d . 1 . . Zn
O1 0.04398(15) 0.05128(11) 0.40604(9) 0.0337(2) Uani d . 1 . . O
O2 0.1765(2) 0.26529(12) 0.73532(10) 0.0450(3) Uani d . 1 . . O
O3 0.39014(17) 0.10438(14) 0.59157(12) 0.0474(3) Uani d . 1 . . O
S1 0.47569(6) 0.03285(5) 0.67222(5) 0.04877(12) Uani d . 1 . . S
N1 0.19441(18) 0.32797(12) 0.52931(11) 0.0313(2) Uani d . 1 . . N
N2 0.20450(19) 0.43653(13) 0.62061(11) 0.0349(3) Uani d . 1 . . N
C1 0.12854(19) 0.10700(15) 0.31867(12) 0.0284(3) Uani d . 1 . . C
C2 0.1213(2) 0.01710(16) 0.21375(13) 0.0353(3) Uani d . 1 . . C
H2 0.0531 -0.0797 0.2050 0.042 Uiso calc R 1 . . H
C3 0.2129(3) 0.06852(18) 0.12297(14) 0.0403(3) Uani d . 1 . . C
H3 0.2049 0.0066 0.0540 0.048 Uiso calc R 1 . . H
C4 0.3163(2) 0.21148(19) 0.13437(14) 0.0417(4) Uani d . 1 . . C
H4 0.3832 0.2460 0.0750 0.050 Uiso calc R 1 . . H
C5 0.3189(2) 0.30231(17) 0.23475(14) 0.0371(3) Uani d . 1 . . C
H5 0.3869 0.3988 0.2411 0.045 Uiso calc R 1 . . H
C6 0.2237(2) 0.25588(15) 0.32816(12) 0.0292(3) Uani d . 1 . . C
C7 0.2284(2) 0.36361(14) 0.42882(13) 0.0306(3) Uani d . 1 . . C
C8 0.2737(3) 0.51533(16) 0.41435(15) 0.0439(4) Uani d . 1 . . C
H8A 0.1941 0.5542 0.4558 0.066 Uiso calc R 1 . . H
H8B 0.2537 0.5188 0.3327 0.066 Uiso calc R 1 . . H
H8C 0.4021 0.5699 0.4453 0.066 Uiso calc R 1 . . H
C9 0.1922(2) 0.39056(15) 0.71993(13) 0.0317(3) Uani d . 1 . . C
C10 0.1986(2) 0.49549(15) 0.82521(13) 0.0322(3) Uani d . 1 . . C
C11 0.1421(2) 0.60873(16) 0.81514(14) 0.0382(3) Uani d . 1 . . C
H11 0.1049 0.6223 0.7413 0.046 Uiso calc R 1 . . H
C12 0.1404(3) 0.70174(18) 0.91395(17) 0.0468(4) Uani d . 1 . . C
H12 0.0993 0.7760 0.9064 0.056 Uiso calc R 1 . . H
C13 0.1995(3) 0.68450(19) 1.02362(16) 0.0487(4) Uani d . 1 . . C
H13 0.1984 0.7470 1.0901 0.058 Uiso calc R 1 . . H
C14 0.2602(3) 0.5742(2) 1.03419(16) 0.0496(4) Uani d . 1 . . C
H14 0.3032 0.5637 1.1078 0.060 Uiso calc R 1 . . H
C15 0.2576(3) 0.47891(18) 0.93562(15) 0.0416(4) Uani d . 1 . . C
H15 0.2956 0.4033 0.9436 0.050 Uiso calc R 1 . . H
C16 0.3582(4) -0.1511(2) 0.6226(2) 0.0628(6) Uani d . 1 . . C
H16A 0.2254 -0.1729 0.6143 0.094 Uiso calc R 1 . . H
H16B 0.3914 -0.2019 0.6782 0.094 Uiso calc R 1 . . H
H16C 0.3936 -0.1788 0.5481 0.094 Uiso calc R 1 . . H
C17 0.3808(3) 0.0488(3) 0.80627(18) 0.0621(5) Uani d . 1 . . C
H17A 0.4184 0.1474 0.8410 0.093 Uiso calc R 1 . . H
H17B 0.4261 0.0004 0.8590 0.093 Uiso calc R 1 . . H
H17C 0.2467 0.0073 0.7911 0.093 Uiso calc R 1 . . H
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'
Zn Zn 0.2839 1.4301 '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
O2 Zn1 O1 . . 155.78(5) yes
O1 Zn1 O2 2_556 . 105.70(6) yes
O1 Zn1 O3 2_556 . 103.94(6) yes
O2 Zn1 O3 . . 101.22(6) yes
O1 Zn1 N1 2_556 . 146.72(5) yes
O2 Zn1 N1 . . 78.70(6) yes
O3 Zn1 N1 . . 107.52(5) yes
O1 Zn1 O1 2_556 . 79.24(5) yes
O3 Zn1 O1 . . 100.46(5) yes
N1 Zn1 O1 . . 84.59(5) yes
O1 Zn1 Zn1 2_556 2_556 40.37(4) ?
O2 Zn1 Zn1 . 2_556 140.73(4) ?
O3 Zn1 Zn1 . 2_556 105.88(5) ?
N1 Zn1 Zn1 . 2_556 118.16(5) ?
O1 Zn1 Zn1 . 2_556 38.87(3) ?
C1 O1 Zn1 . 2_556 134.94(9) ?
C1 O1 Zn1 . . 122.63(9) ?
Zn1 O1 Zn1 2_556 . 100.76(5) ?
C9 O2 Zn1 . . 110.64(10) ?
S1 O3 Zn1 . . 132.71(8) ?
O3 S1 C16 . . 105.77(11) ?
O3 S1 C17 . . 106.45(10) ?
C16 S1 C17 . . 98.33(12) ?
C7 N1 N2 . . 116.66(12) ?
C7 N1 Zn1 . . 129.87(10) ?
N2 N1 Zn1 . . 113.29(10) ?
C9 N2 N1 . . 110.39(12) ?
O1 C1 C2 . . 119.44(13) ?
O1 C1 C6 . . 121.98(12) ?
C2 C1 C6 . . 118.57(13) ?
C3 C2 C1 . . 121.68(14) ?
C3 C2 H2 . . 119.2 ?
C1 C2 H2 . . 119.2 ?
C4 C3 C2 . . 120.16(15) ?
C4 C3 H3 . . 119.9 ?
C2 C3 H3 . . 119.9 ?
C5 C4 C3 . . 119.03(15) ?
C5 C4 H4 . . 120.5 ?
C3 C4 H4 . . 120.5 ?
C4 C5 C6 . . 122.96(15) ?
C4 C5 H5 . . 118.5 ?
C6 C5 H5 . . 118.5 ?
C5 C6 C1 . . 117.35(13) ?
C5 C6 C7 . . 118.22(13) ?
C1 C6 C7 . . 124.43(13) ?
N1 C7 C6 . . 120.18(13) ?
N1 C7 C8 . . 120.15(13) ?
C6 C7 C8 . . 119.68(13) ?
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 . . 126.53(13) ?
O2 C9 C10 . . 117.31(13) ?
N2 C9 C10 . . 116.15(13) ?
C15 C10 C11 . . 118.91(14) ?
C15 C10 C9 . . 120.01(14) ?
C11 C10 C9 . . 121.06(14) ?
C12 C11 C10 . . 120.56(16) ?
C12 C11 H11 . . 119.7 ?
C10 C11 H11 . . 119.7 ?
C13 C12 C11 . . 120.13(17) ?
C13 C12 H12 . . 119.9 ?
C11 C12 H12 . . 119.9 ?
C14 C13 C12 . . 119.66(16) ?
C14 C13 H13 . . 120.2 ?
C12 C13 H13 . . 120.2 ?
C13 C14 C15 . . 120.28(17) ?
C13 C14 H14 . . 119.9 ?
C15 C14 H14 . . 119.9 ?
C10 C15 C14 . . 120.43(17) ?
C10 C15 H15 . . 119.8 ?
C14 C15 H15 . . 119.8 ?
S1 C16 H16A . . 109.5 ?
S1 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
S1 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
S1 C17 H17A . . 109.5 ?
S1 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
S1 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 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
Zn1 O1 2_556 2.0038(13) yes
Zn1 O2 . 2.0117(14) yes
Zn1 O3 . 2.0131(16) yes
Zn1 N1 . 2.0466(16) yes
Zn1 O1 . 2.0683(15) yes
Zn1 Zn1 2_556 3.1370(13) yes
O1 C1 . 1.3391(17) yes
O1 Zn1 2_556 2.0038(13) ?
O2 C9 . 1.2834(19) yes
O3 S1 . 1.5142(14) yes
S1 C16 . 1.761(2) yes
S1 C17 . 1.781(2) yes
N1 C7 . 1.294(2) yes
N1 N2 . 1.3949(17) yes
N2 C9 . 1.309(2) yes
C1 C2 . 1.401(2) ?
C1 C6 . 1.423(2) ?
C2 C3 . 1.381(2) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.379(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.375(2) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.405(2) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.474(2) ?
C7 C8 . 1.504(2) ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 C10 . 1.490(2) ?
C10 C15 . 1.385(2) ?
C10 C11 . 1.387(2) ?
C11 C12 . 1.384(2) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.380(3) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.379(3) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.385(2) ?
C14 H14 . 0.9300 ?
C15 H15 . 0.9300 ?
C16 H16A . 0.9600 ?
C16 H16B . 0.9600 ?
C16 H16C . 0.9600 ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
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
C2 H2 O2 2_556 0.93 2.33 3.167(3) 149 yes
C16 H16C O3 2_656 0.96 2.42 3.258(4) 145 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_4
_geom_torsion
O1 Zn1 O1 C1 2_556 . -167.26(14)
O2 Zn1 O1 C1 . . 88.33(16)
O3 Zn1 O1 C1 . . -64.89(12)
N1 Zn1 O1 C1 . . 41.96(11)
Zn1 Zn1 O1 C1 2_556 . -167.26(14)
O1 Zn1 O1 Zn1 2_556 2_556 0.0000
O2 Zn1 O1 Zn1 . 2_556 -104.41(12)
O3 Zn1 O1 Zn1 . 2_556 102.37(6)
N1 Zn1 O1 Zn1 . 2_556 -150.78(6)
O1 Zn1 O2 C9 2_556 . -140.38(12)
O3 Zn1 O2 C9 . . 111.52(12)
N1 Zn1 O2 C9 . . 5.66(11)
O1 Zn1 O2 C9 . . -41.63(19)
Zn1 Zn1 O2 C9 2_556 . -115.40(11)
O1 Zn1 O3 S1 2_556 . -45.18(12)
O2 Zn1 O3 S1 . . 64.30(13)
N1 Zn1 O3 S1 . . 145.85(11)
O1 Zn1 O3 S1 . . -126.56(12)
Zn1 Zn1 O3 S1 2_556 . -86.98(12)
Zn1 O3 S1 C16 . . 76.50(14)
Zn1 O3 S1 C17 . . -27.41(15)
O1 Zn1 N1 C7 2_556 . -89.04(16)
O2 Zn1 N1 C7 . . 169.51(15)
O3 Zn1 N1 C7 . . 71.18(14)
O1 Zn1 N1 C7 . . -28.11(14)
Zn1 Zn1 N1 C7 2_556 . -48.44(15)
O1 Zn1 N1 N2 2_556 . 96.05(12)
O2 Zn1 N1 N2 . . -5.39(10)
O3 Zn1 N1 N2 . . -103.73(10)
O1 Zn1 N1 N2 . . 156.98(10)
Zn1 Zn1 N1 N2 2_556 . 136.65(9)
C7 N1 N2 C9 . . -171.55(14)
Zn1 N1 N2 C9 . . 4.08(15)
Zn1 O1 C1 C2 2_556 . -15.2(2)
Zn1 O1 C1 C2 . . 146.97(11)
Zn1 O1 C1 C6 2_556 . 163.73(11)
Zn1 O1 C1 C6 . . -34.09(18)
O1 C1 C2 C3 . . -177.18(15)
C6 C1 C2 C3 . . 3.8(2)
C1 C2 C3 C4 . . 0.6(3)
C2 C3 C4 C5 . . -3.2(3)
C3 C4 C5 C6 . . 1.3(3)
C4 C5 C6 C1 . . 3.0(2)
C4 C5 C6 C7 . . -176.88(15)
O1 C1 C6 C5 . . 175.57(14)
C2 C1 C6 C5 . . -5.5(2)
O1 C1 C6 C7 . . -4.5(2)
C2 C1 C6 C7 . . 174.44(14)
N2 N1 C7 C6 . . 179.03(12)
Zn1 N1 C7 C6 . . 4.3(2)
N2 N1 C7 C8 . . -0.7(2)
Zn1 N1 C7 C8 . . -175.49(12)
C5 C6 C7 N1 . . -159.11(14)
C1 C6 C7 N1 . . 21.0(2)
C5 C6 C7 C8 . . 20.7(2)
C1 C6 C7 C8 . . -159.27(15)
Zn1 O2 C9 N2 . . -5.8(2)
Zn1 O2 C9 C10 . . 174.65(10)
N1 N2 C9 O2 . . 1.2(2)
N1 N2 C9 C10 . . -179.26(12)
O2 C9 C10 C15 . . 24.2(2)
N2 C9 C10 C15 . . -155.36(15)
O2 C9 C10 C11 . . -154.23(15)
N2 C9 C10 C11 . . 26.2(2)
C15 C10 C11 C12 . . -1.5(2)
C9 C10 C11 C12 . . 176.98(15)
C10 C11 C12 C13 . . 1.6(3)
C11 C12 C13 C14 . . 0.0(3)
C12 C13 C14 C15 . . -1.6(3)
C11 C10 C15 C14 . . -0.1(3)
C9 C10 C15 C14 . . -178.62(16)
C13 C14 C15 C10 . . 1.7(3)
