#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/24/2212467.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_2212467
loop_
_publ_author_name
'Zhao-Xun Lian'
'Hao-Hong Li'
_publ_section_title
;
 Bis(ethylenediamine-κ²N,N')copper(II)
 9,10-dioxoanthracene-2,6-disulfonate
;
_journal_coeditor_code           BI2162
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m853
_journal_page_last               m855
_journal_paper_doi               10.1107/S1600536807008215
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '[Cu (C2 H8 N2)2] (C14 H6 O8 S2)'
_chemical_formula_moiety         'C4 H16 Cu N4 2+ , C14 H6 O8 S2 2-'
_chemical_formula_sum            'C18 H22 Cu N4 O8 S2'
_chemical_formula_weight         550.06
_chemical_name_systematic
;
Bis(ethylenediamine-κ²N,N')copper(II) 9,10-dioxoanthracene-2,6-disulfonate
;
_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
_cell_angle_alpha                79.231(3)
_cell_angle_beta                 78.946(3)
_cell_angle_gamma                75.258(3)
_cell_formula_units_Z            1
_cell_length_a                   5.9738(11)
_cell_length_b                   8.3196(14)
_cell_length_c                   11.0372(19)
_cell_measurement_reflns_used    4412
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      18
_cell_measurement_theta_min      12
_cell_volume                     515.11(16)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker SMART 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  0.0189
_diffrn_reflns_av_sigmaI/netI    0.0307
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4412
_diffrn_reflns_theta_full        27.04
_diffrn_reflns_theta_max         27.04
_diffrn_reflns_theta_min         1.90
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.321
_exptl_absorpt_correction_T_max  0.77
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.773
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             283
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.229
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         2228
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0331
_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)+(0.0406P)²+0.2691P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0873
_reflns_number_gt                1760
_reflns_number_total             2228
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bi2162.cif
_cod_data_source_block           I
_cod_database_code               2212467
_cod_database_fobs_code          2212467
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
Cu Cu1 0.0000 0.0000 0.5000 0.03089(15) Uani d S 1
S S1 0.30573(11) 0.19633(8) 0.25059(6) 0.02894(16) Uani d . 1
O O1 0.1407(3) 0.3498(2) 0.2788(2) 0.0463(5) Uani d . 1
O O2 0.4030(3) 0.0987(3) 0.36019(17) 0.0415(5) Uani d . 1
O O3 0.2160(4) 0.0968(3) 0.18533(19) 0.0469(5) Uani d . 1
O O4 0.7449(3) 0.6970(2) 0.16757(18) 0.0412(5) Uani d . 1
N N1 0.0702(4) 0.1022(3) 0.6340(2) 0.0340(5) Uani d . 1
H H1A 0.0084 0.0559 0.7093 0.041 Uiso calc R 1
H H1B 0.2261 0.0834 0.6314 0.041 Uiso calc R 1
N N2 -0.2309(4) 0.2193(3) 0.4660(2) 0.0339(5) Uani d . 1
H H2A -0.1750 0.2811 0.3961 0.041 Uiso calc R 1
H H2B -0.3673 0.2008 0.4553 0.041 Uiso calc R 1
C C1 0.5428(4) 0.2597(3) 0.1453(2) 0.0253(5) Uani d . 1
C C2 0.6675(4) 0.1612(3) 0.0547(2) 0.0308(5) Uani d . 1
H H2 0.6242 0.0641 0.0474 0.037 Uiso calc R 1
C C3 0.8557(4) 0.2087(3) -0.0241(2) 0.0297(5) Uani d . 1
H H3 0.9379 0.1439 -0.0855 0.036 Uiso calc R 1
C C4 0.9239(4) 0.3528(3) -0.0127(2) 0.0247(5) Uani d . 1
C C5 0.7957(4) 0.4525(3) 0.0770(2) 0.0238(5) Uani d . 1
C C6 0.6032(4) 0.4060(3) 0.1557(2) 0.0262(5) Uani d . 1
H H6 0.5160 0.4728 0.2149 0.031 Uiso calc R 1
C C7 0.8628(4) 0.6067(3) 0.0930(2) 0.0261(5) Uani d . 1
C C8 -0.0320(6) 0.2842(4) 0.6140(3) 0.0457(7) Uani d . 1
H H8A 0.0694 0.3404 0.5500 0.055 Uiso calc R 1
H H8B -0.0499 0.3307 0.6905 0.055 Uiso calc R 1
C C9 -0.2673(5) 0.3092(4) 0.5739(3) 0.0448(7) Uani d . 1
H H9A -0.3747 0.2647 0.6416 0.054 Uiso calc R 1
H H9B -0.3328 0.4279 0.5508 0.054 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'
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
N1 Cu1 N1 . 2_556 180.0 ?
N1 Cu1 N2 . 2_556 94.83(9) y
N1 Cu1 N2 2_556 2_556 85.17(9) ?
N1 Cu1 N2 . . 85.17(9) y
N1 Cu1 N2 2_556 . 94.83(9) ?
N2 Cu1 N2 2_556 . 180.0 ?
O3 S1 O1 . . 113.59(13) ?
O3 S1 O2 . . 112.45(12) ?
O1 S1 O2 . . 112.11(13) ?
O3 S1 C1 . . 105.75(11) ?
O1 S1 C1 . . 105.80(12) ?
O2 S1 C1 . . 106.42(11) ?
C8 N1 Cu1 . . 108.41(17) ?
C8 N1 H1A . . 110.0 ?
Cu1 N1 H1A . . 110.0 ?
C8 N1 H1B . . 110.0 ?
Cu1 N1 H1B . . 110.0 ?
H1A N1 H1B . . 108.4 ?
C9 N2 Cu1 . . 107.83(17) ?
C9 N2 H2A . . 110.1 ?
Cu1 N2 H2A . . 110.1 ?
C9 N2 H2B . . 110.1 ?
Cu1 N2 H2B . . 110.1 ?
H2A N2 H2B . . 108.5 ?
C6 C1 C2 . . 120.8(2) ?
C6 C1 S1 . . 119.33(19) ?
C2 C1 S1 . . 119.87(18) ?
C3 C2 C1 . . 119.5(2) ?
C3 C2 H2 . . 120.3 ?
C1 C2 H2 . . 120.3 ?
C2 C3 C4 . . 120.6(2) ?
C2 C3 H3 . . 119.7 ?
C4 C3 H3 . . 119.7 ?
C3 C4 C5 . . 119.5(2) ?
C3 C4 C7 . 2_765 119.1(2) ?
C5 C4 C7 . 2_765 121.3(2) ?
C6 C5 C4 . . 119.9(2) ?
C6 C5 C7 . . 118.7(2) ?
C4 C5 C7 . . 121.4(2) ?
C1 C6 C5 . . 119.6(2) ?
C1 C6 H6 . . 120.2 ?
C5 C6 H6 . . 120.2 ?
O4 C7 C4 . 2_765 121.5(2) ?
O4 C7 C5 . . 121.1(2) ?
C4 C7 C5 2_765 . 117.3(2) ?
N1 C8 C9 . . 107.7(2) ?
N1 C8 H8A . . 110.2 ?
C9 C8 H8A . . 110.2 ?
N1 C8 H8B . . 110.2 ?
C9 C8 H8B . . 110.2 ?
H8A C8 H8B . . 108.5 ?
N2 C9 C8 . . 107.3(2) ?
N2 C9 H9A . . 110.2 ?
C8 C9 H9A . . 110.2 ?
N2 C9 H9B . . 110.2 ?
C8 C9 H9B . . 110.2 ?
H9A C9 H9B . . 108.5 ?
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 N1 . 1.994(2) y
Cu1 N1 2_556 1.994(2) ?
Cu1 N2 2_556 2.009(2) ?
Cu1 N2 . 2.009(2) y
S1 O3 . 1.445(2) ?
S1 O1 . 1.445(2) ?
S1 O2 . 1.4569(19) ?
S1 C1 . 1.776(2) ?
O4 C7 . 1.216(3) ?
N1 C8 . 1.473(4) ?
N1 H1A . 0.900 ?
N1 H1B . 0.900 ?
N2 C9 . 1.476(3) ?
N2 H2A . 0.900 ?
N2 H2B . 0.900 ?
C1 C6 . 1.384(3) ?
C1 C2 . 1.392(4) ?
C2 C3 . 1.378(3) ?
C2 H2 . 0.930 ?
C3 C4 . 1.395(3) ?
C3 H3 . 0.930 ?
C4 C5 . 1.396(3) ?
C4 C7 2_765 1.482(3) ?
C5 C6 . 1.394(3) ?
C5 C7 . 1.487(3) ?
C6 H6 . 0.930 ?
C7 C4 2_765 1.482(3) ?
C8 C9 . 1.507(4) ?
C8 H8A . 0.970 ?
C8 H8B . 0.970 ?
C9 H9A . 0.970 ?
C9 H9B . 0.970 ?
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
N1 H1A O3 2_556 0.90 2.12 2.922(3) 148.5
N1 H1B O2 2_656 0.90 2.35 3.172(3) 151.5
N2 H2A O1 . 0.90 2.21 3.000(3) 145.8
N2 H2B O2 1_455 0.90 2.28 3.113(3) 154.4
