#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/75/2217582.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_2217582
loop_
_publ_author_name
'Ali, Hapipah M.'
'Laila, Musalem'
'Rizal, Razali M.'
'Ng, Seik Weng'
_publ_section_title
;Bis{μ-N'-[1-(5-bromo-2-oxidophenyl)ethylidene]benzenesulfonohydrazidato}-κ³O²,N':N;κ³N:O²,N'-bis[(dimethyl
 sulfoxide-κO)copper(II)]
;
_journal_coeditor_code           LH2588
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m414
_journal_page_last               m414
_journal_paper_doi               10.1107/S1600536808002201
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          '[Cu2 (C15 H11 Br N2 O3 S)2 (C2 H6 O S)2]'
_chemical_formula_moiety         'C32 H34 Br2 Cu2 N4 O8 S4'
_chemical_formula_sum            'C32 H34 Br2 Cu2 N4 O8 S4'
_chemical_formula_weight         1017.77
_chemical_name_systematic
;
Bis{μ-N'-[1-(5-bromo-2-
oxidophenyl)ethylidene]benzenesulfonohydrazidato}-
κ³O²,N':N;κ³N:N',O²-bis[(dimethyl sulfoxide-\kO)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                68.1570(10)
_cell_angle_beta                 74.9280(10)
_cell_angle_gamma                70.6910(10)
_cell_formula_units_Z            1
_cell_length_a                   8.08310(10)
_cell_length_b                   10.4972(2)
_cell_length_c                   12.9481(2)
_cell_measurement_reflns_used    7546
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      31.0
_cell_measurement_theta_min      2.7
_cell_volume                     950.56(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, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'φ and ω'
_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  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12330
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.72
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.494
_exptl_absorpt_correction_T_max  0.5416
_exptl_absorpt_correction_T_min  0.3354
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            Green
_exptl_crystal_density_diffrn    1.778
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             510
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.747
_refine_diff_density_min         -0.890
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.206
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         4318
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.206
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0389
_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)+(0.0827P)²+1.8365P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1298
_refine_ls_wR_factor_ref         0.1509
_reflns_number_gt                3788
_reflns_number_total             4318
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2588.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               2217582
_cod_database_fobs_code          2217582
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
Br Br1 0.33316(6) 0.23924(5) 0.54963(4) 0.03789(17) Uani d . 1
Cu Cu1 1.09563(6) 0.32031(5) 0.10740(4) 0.02020(15) Uani d . 1
S S1 1.13219(13) 0.63204(10) 0.05283(8) 0.0213(2) Uani d . 1
S S2 1.41379(13) 0.06832(10) 0.18255(8) 0.0230(2) Uani d . 1
O O1 1.0528(4) 0.2167(3) 0.2622(3) 0.0285(6) Uani d . 1
O O2 1.2628(4) 0.4956(3) 0.0677(3) 0.0278(6) Uani d . 1
O O3 1.1615(4) 0.7489(3) -0.0472(3) 0.0292(7) Uani d . 1
O O4 1.3150(4) 0.1704(3) 0.0840(2) 0.0253(6) Uani d . 1
N N1 0.9142(4) 0.4879(3) 0.1354(3) 0.0195(6) Uani d . 1
N N2 0.9352(4) 0.6205(3) 0.0558(3) 0.0198(6) Uani d . 1
C C1 0.8917(5) 0.2298(4) 0.3191(3) 0.0219(8) Uani d . 1
C C2 0.8558(6) 0.1098(5) 0.4082(3) 0.0269(9) Uani d . 1
H H2 0.9472 0.0236 0.4212 0.032 Uiso calc R 1
C C3 0.6946(6) 0.1120(5) 0.4770(3) 0.0274(9) Uani d . 1
H H3 0.6759 0.0294 0.5370 0.033 Uiso calc R 1
C C4 0.5591(6) 0.2368(5) 0.4575(3) 0.0249(8) Uani d . 1
C C5 0.5843(5) 0.3557(4) 0.3695(4) 0.0243(8) Uani d . 1
H H5 0.4889 0.4393 0.3569 0.029 Uiso calc R 1
C C6 0.7481(5) 0.3565(4) 0.2975(3) 0.0208(7) Uani d . 1
C C7 0.7691(5) 0.4889(4) 0.2075(3) 0.0217(8) Uani d . 1
C C8 0.6221(7) 0.6230(5) 0.1999(5) 0.0392(12) Uani d . 1
H H8A 0.6631 0.7033 0.1428 0.059 Uiso calc R 1
H H8B 0.5875 0.6396 0.2731 0.059 Uiso calc R 1
H H8C 0.5198 0.6135 0.1788 0.059 Uiso calc R 1
C C10 1.1190(5) 0.6831(4) 0.1713(3) 0.0220(8) Uani d . 1
C C11 1.1381(6) 0.5793(5) 0.2752(4) 0.0269(8) Uani d . 1
H H11 1.1558 0.4822 0.2833 0.032 Uiso calc R 1
C C12 1.1307(6) 0.6200(5) 0.3673(4) 0.0318(9) Uani d . 1
H H12 1.1418 0.5505 0.4393 0.038 Uiso calc R 1
C C13 1.1072(6) 0.7618(5) 0.3547(4) 0.0327(10) Uani d . 1
H H13 1.1064 0.7884 0.4174 0.039 Uiso calc R 1
C C14 1.0849(6) 0.8649(5) 0.2507(4) 0.0304(9) Uani d . 1
H H14 1.0656 0.9622 0.2429 0.036 Uiso calc R 1
C C15 1.0910(6) 0.8258(4) 0.1583(4) 0.0249(8) Uani d . 1
H H15 1.0761 0.8957 0.0869 0.030 Uiso calc R 1
C C16 1.6285(6) 0.0005(5) 0.1132(4) 0.0294(9) Uani d . 1
H H16A 1.6190 -0.0542 0.0690 0.044 Uiso calc R 1
H H16B 1.7060 -0.0613 0.1694 0.044 Uiso calc R 1
H H16C 1.6786 0.0797 0.0631 0.044 Uiso calc R 1
C C17 1.4719(6) 0.1775(5) 0.2371(4) 0.0310(9) Uani d . 1
H H17A 1.3669 0.2215 0.2823 0.046 Uiso calc R 1
H H17B 1.5168 0.2519 0.1746 0.046 Uiso calc R 1
H H17C 1.5640 0.1193 0.2844 0.046 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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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_3
_geom_angle
O1 Cu1 N1 . 89.77(13)
O1 Cu1 O4 . 91.02(13)
N1 Cu1 O4 . 167.44(13)
O1 Cu1 N2 2_765 153.28(14)
N1 Cu1 N2 2_765 93.89(13)
O4 Cu1 N2 2_765 91.03(13)
O3 S1 O2 . 118.67(19)
O3 S1 N2 . 105.18(18)
O2 S1 N2 . 112.07(17)
O3 S1 C10 . 107.86(19)
O2 S1 C10 . 106.05(19)
N2 S1 C10 . 106.37(18)
O4 S2 C17 . 105.9(2)
O4 S2 C16 . 102.9(2)
C17 S2 C16 . 98.1(2)
C1 O1 Cu1 . 121.3(3)
S2 O4 Cu1 . 120.97(17)
C7 N1 N2 . 117.5(3)
C7 N1 Cu1 . 127.0(3)
N2 N1 Cu1 . 114.7(2)
N1 N2 S1 . 108.2(2)
N1 N2 Cu1 2_765 122.8(2)
S1 N2 Cu1 2_765 105.85(17)
O1 C1 C2 . 117.5(4)
O1 C1 C6 . 125.2(4)
C2 C1 C6 . 117.3(4)
C3 C2 C1 . 122.9(4)
C3 C2 H2 . 118.5
C1 C2 H2 . 118.5
C2 C3 C4 . 119.0(4)
C2 C3 H3 . 120.5
C4 C3 H3 . 120.5
C5 C4 C3 . 120.7(4)
C5 C4 Br1 . 119.9(3)
C3 C4 Br1 . 119.3(3)
C4 C5 C6 . 121.5(4)
C4 C5 H5 . 119.2
C6 C5 H5 . 119.2
C5 C6 C1 . 118.4(4)
C5 C6 C7 . 119.0(4)
C1 C6 C7 . 122.5(4)
N1 C7 C6 . 119.4(3)
N1 C7 C8 . 120.8(4)
C6 C7 C8 . 119.7(4)
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
C11 C10 C15 . 121.3(4)
C11 C10 S1 . 119.2(3)
C15 C10 S1 . 119.5(3)
C10 C11 C12 . 118.8(4)
C10 C11 H11 . 120.6
C12 C11 H11 . 120.6
C13 C12 C11 . 120.3(4)
C13 C12 H12 . 119.8
C11 C12 H12 . 119.8
C12 C13 C14 . 120.3(4)
C12 C13 H13 . 119.9
C14 C13 H13 . 119.9
C15 C14 C13 . 119.9(4)
C15 C14 H14 . 120.0
C13 C14 H14 . 120.0
C14 C15 C10 . 119.3(4)
C14 C15 H15 . 120.4
C10 C15 H15 . 120.4
S2 C16 H16A . 109.5
S2 C16 H16B . 109.5
H16A C16 H16B . 109.5
S2 C16 H16C . 109.5
H16A C16 H16C . 109.5
H16B C16 H16C . 109.5
S2 C17 H17A . 109.5
S2 C17 H17B . 109.5
H17A C17 H17B . 109.5
S2 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
Br1 C4 . 1.902(4) ?
Cu1 O1 . 1.894(3) yes
Cu1 O4 . 1.986(3) yes
Cu1 N1 . 1.967(3) yes
Cu1 N2 2_765 2.026(3) yes
S1 O3 . 1.445(3) ?
S1 O2 . 1.450(3) ?
S1 N2 . 1.626(3) ?
S1 C10 . 1.772(4) ?
S2 O4 . 1.537(3) ?
S2 C17 . 1.779(4) ?
S2 C16 . 1.781(4) ?
O1 C1 . 1.310(5) ?
N1 C7 . 1.295(5) ?
N1 N2 . 1.423(4) ?
N2 Cu1 2_765 2.026(3) ?
C1 C2 . 1.410(6) ?
C1 C6 . 1.438(5) ?
C2 C3 . 1.372(6) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.388(6) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.374(6) ?
C5 C6 . 1.407(6) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.472(5) ?
C7 C8 . 1.501(6) ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
C10 C11 . 1.388(6) ?
C10 C15 . 1.390(6) ?
C11 C12 . 1.391(6) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.387(7) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.389(7) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.388(6) ?
C14 H14 . 0.9500 ?
C15 H15 . 0.9500 ?
C16 H16A . 0.9800 ?
C16 H16B . 0.9800 ?
C16 H16C . 0.9800 ?
C17 H17A . 0.9800 ?
C17 H17B . 0.9800 ?
C17 H17C . 0.9800 ?
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
N1 Cu1 O1 C1 . . 40.0(3)
O4 Cu1 O1 C1 . . -152.5(3)
N2 Cu1 O1 C1 2_765 . -58.2(5)
C17 S2 O4 Cu1 . . -58.7(3)
C16 S2 O4 Cu1 . . -161.2(2)
O1 Cu1 O4 S2 . . -23.1(2)
N1 Cu1 O4 S2 . . 70.5(7)
N2 Cu1 O4 S2 2_765 . -176.4(2)
O1 Cu1 N1 C7 . . -34.4(4)
O4 Cu1 N1 C7 . . -128.1(6)
N2 Cu1 N1 C7 2_765 . 119.1(3)
O1 Cu1 N1 N2 . . 155.5(3)
O4 Cu1 N1 N2 . . 61.8(7)
N2 Cu1 N1 N2 2_765 . -51.0(3)
C7 N1 N2 S1 . . 132.6(3)
Cu1 N1 N2 S1 . . -56.4(3)
C7 N1 N2 Cu1 . 2_765 -103.8(4)
Cu1 N1 N2 Cu1 . 2_765 67.3(3)
O3 S1 N2 N1 . . 166.0(2)
O2 S1 N2 N1 . . 35.8(3)
C10 S1 N2 N1 . . -79.7(3)
O3 S1 N2 Cu1 . 2_765 32.7(2)
O2 S1 N2 Cu1 . 2_765 -97.6(2)
C10 S1 N2 Cu1 . 2_765 146.95(18)
Cu1 O1 C1 C2 . . 148.7(3)
Cu1 O1 C1 C6 . . -30.8(5)
O1 C1 C2 C3 . . 177.1(4)
C6 C1 C2 C3 . . -3.3(6)
C1 C2 C3 C4 . . 1.1(7)
C2 C3 C4 C5 . . 1.3(7)
C2 C3 C4 Br1 . . 178.2(3)
C3 C4 C5 C6 . . -1.3(7)
Br1 C4 C5 C6 . . -178.1(3)
C4 C5 C6 C1 . . -1.1(6)
C4 C5 C6 C7 . . -177.5(4)
O1 C1 C6 C5 . . -177.2(4)
C2 C1 C6 C5 . . 3.2(6)
O1 C1 C6 C7 . . -0.9(6)
C2 C1 C6 C7 . . 179.6(4)
N2 N1 C7 C6 . . -174.7(3)
Cu1 N1 C7 C6 . . 15.4(5)
N2 N1 C7 C8 . . 5.6(6)
Cu1 N1 C7 C8 . . -164.3(4)
C5 C6 C7 N1 . . -174.6(4)
C1 C6 C7 N1 . . 9.1(6)
C5 C6 C7 C8 . . 5.1(6)
C1 C6 C7 C8 . . -171.2(4)
O3 S1 C10 C11 . . -163.2(3)
O2 S1 C10 C11 . . -35.1(4)
N2 S1 C10 C11 . . 84.4(4)
O3 S1 C10 C15 . . 16.4(4)
O2 S1 C10 C15 . . 144.5(3)
N2 S1 C10 C15 . . -96.0(3)
C15 C10 C11 C12 . . -0.7(6)
S1 C10 C11 C12 . . 178.8(3)
C10 C11 C12 C13 . . -0.9(7)
C11 C12 C13 C14 . . 2.1(7)
C12 C13 C14 C15 . . -1.7(7)
C13 C14 C15 C10 . . 0.1(7)
C11 C10 C15 C14 . . 1.1(6)
S1 C10 C15 C14 . . -178.5(3)
