#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/39/2213908.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_2213908
loop_
_publ_author_name
'Mei, Guang-Quan '
'Huang, Ke-Long'
_publ_section_title
;{Dimethyl
 [2,2'-(ethane-1,2-diyldioxy)bis(benzylidenehydrazono)]bis(dithioformato)-κ⁴S,N,N',S'}copper(II)
;
_journal_coeditor_code           NG2251
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1653
_journal_page_last               m1653
_journal_paper_doi               10.1107/S1600536807022295
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '[Cu (C20 H20 N4 O2 S4)]'
_chemical_formula_moiety         'C20 H20 Cu N4 O2 S4'
_chemical_formula_sum            'C20 H20 Cu N4 O2 S4'
_chemical_formula_weight         540.23
_chemical_name_systematic
;
{Dimethyl
[2,2'-(ethane-1,2-diyldioxy)bis(benzylidenehydrazono)]bis(dithioformato)-
κ⁴S,N,N',S'}copper(II)
;
_space_group_IT_number           45
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'I 2 -2c'
_symmetry_space_group_name_H-M   'I b a 2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.634(2)
_cell_length_b                   12.983(2)
_cell_length_c                   14.908(3)
_cell_measurement_reflns_used    516
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.58
_cell_measurement_theta_min      3.14
_cell_volume                     2251.8(7)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0509
_diffrn_reflns_av_sigmaI/netI    0.0771
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5393
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.35
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.367
_exptl_absorpt_correction_T_max  0.872
_exptl_absorpt_correction_T_min  0.782
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1108
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.557
_refine_diff_density_min         -0.589
_refine_ls_abs_structure_details 'Flack (1983), from 942 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.03(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         1985
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0420
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.005P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0587
_refine_ls_wR_factor_ref         0.0610
_reflns_number_gt                1557
_reflns_number_total             1985
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ng2251.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 'Orthorhombic' changed to
'orthorhombic' 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               2213908
_cod_database_fobs_code          2213908
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'x+1, -y+1, z+1/2'
'-x+1, y+1, 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
Cu Cu1 0.5000 1.0000 0.68635(6) 0.0349(2) Uani d S 1
N N1 0.5939(3) 0.8681(3) 0.6945(3) 0.0355(9) Uani d . 1
N N2 0.6911(3) 0.8713(3) 0.7513(2) 0.0368(10) Uani d . 1
O O1 0.4892(3) 0.8974(2) 0.5277(2) 0.0491(9) Uani d . 1
C C7 0.4388(4) 0.8036(4) 0.5383(3) 0.0378(12) Uani d . 1
C C6 0.3541(4) 0.7662(4) 0.4830(3) 0.0476(15) Uani d . 1
H H6 0.3259 0.8068 0.4366 0.057 Uiso calc R 1
C C5 0.3112(5) 0.6691(5) 0.4963(4) 0.0570(16) Uani d . 1
H H5 0.2510 0.6457 0.4606 0.068 Uiso calc R 1
C C4 0.3548(5) 0.6071(4) 0.5603(4) 0.0600(18) Uani d . 1
H H4 0.3261 0.5408 0.5676 0.072 Uiso calc R 1
C C3 0.4430(5) 0.6425(4) 0.6154(4) 0.0531(16) Uani d . 1
H H3 0.4745 0.5989 0.6584 0.064 Uiso calc R 1
C C2 0.4845(5) 0.7431(3) 0.6066(3) 0.0392(13) Uani d . 1
C C1 0.5741(4) 0.7768(3) 0.6668(3) 0.0401(13) Uani d . 1
H H1 0.6233 0.7258 0.6880 0.048 Uiso calc R 1
C C10 0.4623(4) 0.9540(3) 0.4493(4) 0.0472(15) Uani d . 1
H H10A 0.3821 0.9745 0.4498 0.057 Uiso calc R 1
H H10B 0.4762 0.9126 0.3962 0.057 Uiso calc R 1
S S1 0.66889(11) 1.07741(9) 0.72688(11) 0.0513(4) Uani d . 1
S S2 0.85065(12) 0.97951(11) 0.83033(10) 0.0638(5) Uani d . 1
C C8 0.7281(4) 0.9633(4) 0.7652(3) 0.0441(14) Uani d . 1
C C9 0.8979(4) 0.8506(4) 0.8538(4) 0.0684(19) Uani d . 1
H H9A 0.8364 0.8032 0.8422 0.103 Uiso calc R 1
H H9B 0.9205 0.8457 0.9156 0.103 Uiso calc R 1
H H9C 0.9623 0.8341 0.8161 0.103 Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cu1 0.0355(5) 0.0335(4) 0.0357(4) -0.0002(4) 0.000 0.000
N1 0.032(2) 0.034(2) 0.041(3) -0.0024(16) -0.001(2) -0.005(2)
N2 0.032(2) 0.044(3) 0.034(3) 0.0000(19) -0.0069(19) 0.004(2)
O1 0.066(3) 0.035(2) 0.047(2) -0.0108(18) -0.023(2) 0.0052(17)
C7 0.041(3) 0.028(3) 0.045(3) -0.004(2) 0.002(3) -0.001(3)
C6 0.053(4) 0.037(4) 0.053(4) -0.006(3) -0.008(3) -0.004(3)
C5 0.052(4) 0.059(4) 0.060(4) -0.009(3) -0.010(3) -0.009(3)
C4 0.070(5) 0.050(4) 0.060(4) -0.025(3) 0.008(4) -0.013(3)
C3 0.072(4) 0.037(3) 0.050(4) -0.006(3) 0.005(3) 0.002(3)
C2 0.045(3) 0.032(3) 0.041(3) -0.002(3) 0.004(3) -0.005(2)
C1 0.041(3) 0.042(3) 0.038(4) 0.005(2) 0.003(3) 0.005(3)
C10 0.069(4) 0.047(3) 0.026(3) 0.000(2) -0.007(3) -0.002(3)
S1 0.0401(7) 0.0390(7) 0.0746(10) -0.0035(6) -0.0068(8) -0.0048(8)
S2 0.0411(9) 0.0754(12) 0.0749(11) -0.0001(7) -0.0160(8) -0.0220(9)
C8 0.038(3) 0.055(4) 0.039(3) -0.001(3) 0.006(3) -0.011(3)
C9 0.047(4) 0.088(5) 0.070(5) 0.011(3) -0.010(3) 0.014(4)
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'
O O 0.0106 0.0060 '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'
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'
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
N1 Cu1 N1 2_675 . 173.2(2)
N1 Cu1 S1 2_675 2_675 83.85(10)
N1 Cu1 S1 . 2_675 94.34(10)
N1 Cu1 S1 2_675 . 94.34(10)
N1 Cu1 S1 . . 83.85(10)
S1 Cu1 S1 2_675 . 149.38(9)
C1 N1 N2 . . 111.4(4)
C1 N1 Cu1 . . 131.7(3)
N2 N1 Cu1 . . 116.1(3)
C8 N2 N1 . . 113.1(4)
C7 O1 C10 . . 117.8(4)
O1 C7 C6 . . 123.7(5)
O1 C7 C2 . . 115.2(4)
C6 C7 C2 . . 120.9(5)
C5 C6 C7 . . 120.0(5)
C5 C6 H6 . . 120.0
C7 C6 H6 . . 120.0
C4 C5 C6 . . 121.0(6)
C4 C5 H5 . . 119.5
C6 C5 H5 . . 119.5
C5 C4 C3 . . 119.9(5)
C5 C4 H4 . . 120.0
C3 C4 H4 . . 120.0
C4 C3 C2 . . 120.5(5)
C4 C3 H3 . . 119.8
C2 C3 H3 . . 119.8
C7 C2 C3 . . 117.6(5)
C7 C2 C1 . . 124.0(4)
C3 C2 C1 . . 118.3(5)
N1 C1 C2 . . 127.8(4)
N1 C1 H1 . . 116.1
C2 C1 H1 . . 116.1
O1 C10 C10 . 2_675 106.7(3)
O1 C10 H10A . . 110.4
C10 C10 H10A 2_675 . 110.4
O1 C10 H10B . . 110.4
C10 C10 H10B 2_675 . 110.4
H10A C10 H10B . . 108.6
C8 S1 Cu1 . . 93.03(17)
C8 S2 C9 . . 104.3(2)
N2 C8 S1 . . 127.5(4)
N2 C8 S2 . . 118.5(4)
S1 C8 S2 . . 114.0(3)
S2 C9 H9A . . 109.5
S2 C9 H9B . . 109.5
H9A C9 H9B . . 109.5
S2 C9 H9C . . 109.5
H9A C9 H9C . . 109.5
H9B C9 H9C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cu1 N1 2_675 2.035(3)
Cu1 N1 . 2.035(3)
Cu1 S1 2_675 2.2882(13)
Cu1 S1 . 2.2882(13)
N1 C1 . 1.276(5)
N1 N2 . 1.413(4)
N2 C8 . 1.287(5)
O1 C7 . 1.361(5)
O1 C10 . 1.416(5)
C7 C6 . 1.373(6)
C7 C2 . 1.392(6)
C6 C5 . 1.370(7)
C6 H6 . 0.9300
C5 C4 . 1.348(7)
C5 H5 . 0.9300
C4 C3 . 1.392(7)
C4 H4 . 0.9300
C3 C2 . 1.398(6)
C3 H3 . 0.9300
C2 C1 . 1.444(6)
C1 H1 . 0.9300
C10 C10 2_675 1.482(8)
C10 H10A . 0.9700
C10 H10B . 0.9700
S1 C8 . 1.731(5)
S2 C8 . 1.738(5)
S2 C9 . 1.796(5)
C9 H9A . 0.9600
C9 H9B . 0.9600
C9 H9C . 0.9600
