#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/64/2216486.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_2216486
loop_
_publ_author_name
'Ali, Hapipah M.'
'Yusnita, Juahir'
'Rizal, Mohd. Razali'
'Ng, Seik Weng'
_publ_section_title
'[2'-(5-Chloro-2-oxidobenzylidene)benzenesulfonohydrazide-κ²N,O][2'-(2-oxidobenzylidene)benzenesulfonohydrazide-κ²N,O]copper(II)'
_journal_coeditor_code           HB2629
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m2937
_journal_page_last               m2937
_journal_paper_doi               10.1107/S1600536807055663
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '[Cu (C13 H10 Cl N2 O3 S) (C13 H11 N2 O3 S)]'
_chemical_formula_moiety         'C26 H21 Cl Cu N4 O6 S2'
_chemical_formula_sum            'C26 H21 Cl Cu N4 O6 S2'
_chemical_formula_weight         648.61
_chemical_name_systematic
;
[2'-(5-Chloro-2-oxidobenzylidene)benzenesulfonohydrazide-
κ²N,O][2'-(2-oxidobenzylidene)benzenesulfonohydrazide-
κ²N,O)]copper(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                104.3930(10)
_cell_angle_beta                 111.0910(10)
_cell_angle_gamma                104.6350(10)
_cell_formula_units_Z            1
_cell_length_a                   7.9801(2)
_cell_length_b                   9.9993(2)
_cell_length_c                   10.0823(2)
_cell_measurement_reflns_used    4328
_cell_measurement_temperature    106(2)
_cell_measurement_theta_max      31.7
_cell_measurement_theta_min      2.3
_cell_volume                     672.96(3)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'X-Seed (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      106(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX-II diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'medium-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0157
_diffrn_reflns_av_sigmaI/netI    0.0214
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6161
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.27
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.116
_exptl_absorpt_correction_T_max  0.800
_exptl_absorpt_correction_T_min  0.621
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Gold
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'Irregular block'
_exptl_crystal_F_000             331
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.368
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.197
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3026
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.197
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0307
_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)+(0.0623P)²+0.3245P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.1143
_reflns_number_gt                2769
_reflns_number_total             3026
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb2629.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               2216486
_cod_database_fobs_code          2216486
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Cu Cu1 0.5000 0.5000 0.5000 0.02500(14) Uani d S 1 . .
Cl Cl1 0.1626(2) -0.10643(15) -0.20334(14) 0.0409(3) Uani d P 0.50 A 1
S S1 0.45362(9) 0.19783(6) 0.68120(8) 0.03327(17) Uani d . 1 . .
O O1 0.2978(2) 0.41982(17) 0.2953(2) 0.0307(4) Uani d . 1 . .
N N1 0.5095(3) 0.3035(2) 0.4831(2) 0.0280(4) Uani d . 1 . .
N N2 0.6053(3) 0.2800(2) 0.6200(3) 0.0313(4) Uani d D 1 . .
H H2N 0.691(4) 0.363(2) 0.695(3) 0.042(8) Uiso d D 1 . .
O O2 0.3354(3) 0.05096(19) 0.5676(3) 0.0431(5) Uani d . 1 . .
O O3 0.5800(3) 0.2193(2) 0.8345(3) 0.0469(5) Uani d . 1 . .
C C1 0.2593(3) 0.2975(3) 0.1829(3) 0.0316(5) Uani d . 1 A .
C C2 0.1386(4) 0.2744(3) 0.0309(3) 0.0391(6) Uani d . 1 . .
H H2 0.0805 0.3440 0.0118 0.047 Uiso calc R 1 . .
C C3 0.1027(5) 0.1518(3) -0.0915(3) 0.0448(7) Uani d . 1 A .
H H3 0.0224 0.1390 -0.1934 0.054 Uiso calc R 1 . .
C C4 0.1844(5) 0.0473(3) -0.0649(4) 0.0478(7) Uani d . 1 . .
H H4 0.1626 -0.0349 -0.1493 0.057 Uiso calc PR 0.50 A 2
C C5 0.2947(4) 0.0620(3) 0.0803(4) 0.0422(6) Uani d . 1 A .
H H5 0.3449 -0.0122 0.0967 0.051 Uiso calc R 1 . .
C C6 0.3359(4) 0.1868(2) 0.2076(3) 0.0325(5) Uani d . 1 . .
C C7 0.4457(3) 0.1906(2) 0.3564(3) 0.0319(5) Uani d . 1 A .
H H7 0.4740 0.1051 0.3635 0.038 Uiso calc R 1 . .
C C8 0.3039(3) 0.2999(3) 0.6841(3) 0.0313(5) Uani d . 1 . .
C C9 0.1162(4) 0.2416(3) 0.5700(4) 0.0416(6) Uani d . 1 . .
H H9 0.0649 0.1455 0.4920 0.050 Uiso calc R 1 . .
C C10 0.0038(4) 0.3275(4) 0.5720(4) 0.0526(8) Uani d . 1 . .
H H10 -0.1263 0.2896 0.4945 0.063 Uiso calc R 1 . .
C C11 0.0797(4) 0.4675(4) 0.6855(4) 0.0486(7) Uani d . 1 . .
H H11 0.0015 0.5252 0.6848 0.058 Uiso calc R 1 . .
C C12 0.2683(4) 0.5243(3) 0.8000(4) 0.0412(6) Uani d . 1 . .
H H12 0.3194 0.6202 0.8781 0.049 Uiso calc R 1 . .
C C13 0.3824(4) 0.4401(3) 0.7998(3) 0.0338(5) Uani d . 1 . .
H H13 0.5123 0.4777 0.8777 0.041 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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
O1 Cu1 O1 2_666 . 180.0
O1 Cu1 N1 2_666 2_666 91.01(8)
O1 Cu1 N1 . 2_666 88.99(8)
O1 Cu1 N1 2_666 . 88.99(8)
O1 Cu1 N1 . . 91.01(8)
N1 Cu1 N1 2_666 . 180.0
O2 S1 O3 . . 120.67(12)
O2 S1 N2 . . 106.95(12)
O3 S1 N2 . . 103.56(12)
O2 S1 C8 . . 108.21(12)
O3 S1 C8 . . 110.29(12)
N2 S1 C8 . . 106.12(10)
C1 O1 Cu1 . . 126.98(15)
C7 N1 N2 . . 114.94(18)
C7 N1 Cu1 . . 126.16(17)
N2 N1 Cu1 . . 118.78(15)
N1 N2 S1 . . 113.53(15)
N1 N2 H2N . . 112(2)
S1 N2 H2N . . 108(2)
O1 C1 C2 . . 119.2(2)
O1 C1 C6 . . 123.1(2)
C2 C1 C6 . . 117.7(2)
C3 C2 C1 . . 121.3(3)
C3 C2 H2 . . 119.4
C1 C2 H2 . . 119.4
C4 C3 C2 . . 120.0(3)
C4 C3 H3 . . 120.0
C2 C3 H3 . . 120.0
C5 C4 C3 . . 120.6(3)
C5 C4 Cl1 . . 113.5(2)
C3 C4 Cl1 . . 126.0(3)
C5 C4 H4 . . 119.7
C3 C4 H4 . . 119.7
C4 C5 C6 . . 120.7(3)
C4 C5 H5 . . 119.6
C6 C5 H5 . . 119.6
C5 C6 C7 . . 117.2(2)
C5 C6 C1 . . 119.6(3)
C7 C6 C1 . . 123.1(2)
N1 C7 C6 . . 124.2(2)
N1 C7 H7 . . 117.9
C6 C7 H7 . . 117.9
C9 C8 C13 . . 122.1(2)
C9 C8 S1 . . 119.4(2)
C13 C8 S1 . . 118.46(19)
C8 C9 C10 . . 118.1(3)
C8 C9 H9 . . 121.0
C10 C9 H9 . . 121.0
C11 C10 C9 . . 120.7(3)
C11 C10 H10 . . 119.7
C9 C10 H10 . . 119.7
C12 C11 C10 . . 120.6(3)
C12 C11 H11 . . 119.7
C10 C11 H11 . . 119.7
C11 C12 C13 . . 119.5(3)
C11 C12 H12 . . 120.2
C13 C12 H12 . . 120.2
C12 C13 C8 . . 119.1(3)
C12 C13 H13 . . 120.5
C8 C13 H13 . . 120.5
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
Cu1 O1 2_666 1.9062(18) ?
Cu1 O1 . 1.9062(18) y
Cu1 N1 2_666 1.9532(17) ?
Cu1 N1 . 1.9532(17) y
Cl1 C4 . 1.721(3) ?
S1 O2 . 1.430(2) ?
S1 O3 . 1.434(2) ?
S1 N2 . 1.676(2) ?
S1 C8 . 1.760(2) ?
O1 C1 . 1.321(3) ?
N1 C7 . 1.300(3) ?
N1 N2 . 1.427(3) ?
N2 H2N . 0.87(3) ?
C1 C2 . 1.406(4) ?
C1 C6 . 1.425(3) ?
C2 C3 . 1.387(4) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.395(5) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.356(5) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.416(4) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.424(4) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.375(4) ?
C8 C13 . 1.392(4) ?
C9 C10 . 1.392(4) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.383(5) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.383(4) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.387(3) ?
C12 H12 . 0.9500 ?
C13 H13 . 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
N2 H2N O1 2_666 0.87(3) 2.13(3) 2.723(2) 125(3) 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
N1 Cu1 O1 C1 2_666 155.72(18)
N1 Cu1 O1 C1 . -24.28(18)
O1 Cu1 N1 C7 2_666 -159.40(19)
O1 Cu1 N1 C7 . 20.60(19)
O1 Cu1 N1 N2 2_666 16.33(15)
O1 Cu1 N1 N2 . -163.67(15)
C7 N1 N2 S1 . -85.6(2)
Cu1 N1 N2 S1 . 98.25(16)
O2 S1 N2 N1 . 65.37(18)
O3 S1 N2 N1 . -166.16(16)
C8 S1 N2 N1 . -49.98(19)
Cu1 O1 C1 C2 . -164.03(17)
Cu1 O1 C1 C6 . 15.5(3)
O1 C1 C2 C3 . 176.4(2)
C6 C1 C2 C3 . -3.1(4)
C1 C2 C3 C4 . 1.1(4)
C2 C3 C4 C5 . 1.9(4)
C2 C3 C4 Cl1 . -177.3(2)
C3 C4 C5 C6 . -2.6(4)
Cl1 C4 C5 C6 . 176.62(19)
C4 C5 C6 C7 . 177.3(2)
C4 C5 C6 C1 . 0.5(4)
O1 C1 C6 C5 . -177.2(2)
C2 C1 C6 C5 . 2.3(3)
O1 C1 C6 C7 . 6.2(3)
C2 C1 C6 C7 . -174.3(2)
N2 N1 C7 C6 . 176.1(2)
Cu1 N1 C7 C6 . -8.1(3)
C5 C6 C7 N1 . 173.5(2)
C1 C6 C7 N1 . -9.8(4)
O2 S1 C8 C9 . -10.6(2)
O3 S1 C8 C9 . -144.6(2)
N2 S1 C8 C9 . 103.9(2)
O2 S1 C8 C13 . 171.64(18)
O3 S1 C8 C13 . 37.7(2)
N2 S1 C8 C13 . -73.9(2)
C13 C8 C9 C10 . 0.2(4)
S1 C8 C9 C10 . -177.5(2)
C8 C9 C10 C11 . 0.2(5)
C9 C10 C11 C12 . -0.5(5)
C10 C11 C12 C13 . 0.5(4)
C11 C12 C13 C8 . -0.1(4)
C9 C8 C13 C12 . -0.3(4)
S1 C8 C13 C12 . 177.43(18)
