#------------------------------------------------------------------------------
#$Date: 2009-11-16 01:43:51 +0000 (Mon, 16 Nov 2009) $
#$Revision: 853 $
#$URL: svn://www.crystallography.net/cod/cif/2/2202581.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2202581
_journal_name_full  'Acta Crystallographica, Section E'
_journal_year  2003
_journal_volume  59
_journal_page_first  m889
_journal_page_last  m891
_publ_section_title
;
Bis-dicyanamide(2,2-bipyridine N,N'-dioxide-O,O')-copper(II)
;
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
loop_
_publ_author_name
  'Albada, Gerard A. van'
  'Mutikainen, Ilpo'
  'Turpeinen, Urho'
  'Reedijk, Jan'
_chemical_formula_sum  'C24 H16 Cu N10 O4'
_chemical_formula_iupac  '[Cu (C10 H8 N2 O2 )2 (C2 N3 )]'
_chemical_formula_weight  572.01
_symmetry_cell_setting  monoclinic
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x, -y-1/2, z-1/2'
_cell_length_a  6.8650(10)
_cell_length_b  21.647(3)
_cell_length_c  17.214(3)
_cell_angle_alpha  90.00
_cell_angle_beta  113.21(2)
_cell_angle_gamma  90.00
_cell_volume  2351.1(6)
_cell_formula_units_Z  4
_cell_measurement_temperature  173(2)
_exptl_crystal_density_diffrn  1.616
_diffrn_ambient_temperature  173(2)
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
  Cu1 0.84283(6) 0.23956(2) 0.43474(3) 0.01678(14) Uani d . 1 . . Cu
  N11 1.1944(4) 0.31564(14) 0.57347(16) 0.0173(7) Uani d . 1 . . N
  C12 1.3790(5) 0.28725(17) 0.5815(2) 0.0177(8) Uani d . 1 . . C
  C13 1.5577(5) 0.32309(18) 0.5945(2) 0.0219(8) Uani d . 1 . . C
  H131 1.6881 0.3036 0.6025 0.026 Uiso calc R 1 . . H
  C14 1.5471(5) 0.38649(19) 0.5959(2) 0.0269(9) Uani d . 1 . . C
  H141 1.6690 0.4109 0.6049 0.032 Uiso calc R 1 . . H
  C15 1.3547(5) 0.41412(19) 0.5841(2) 0.0275(9) Uani d . 1 . . C
  H151 1.3427 0.4579 0.5834 0.033 Uiso calc R 1 . . H
  C16 1.1814(5) 0.37760(17) 0.5731(2) 0.0228(8) Uani d . 1 . . C
  H161 1.0501 0.3966 0.5652 0.027 Uiso calc R 1 . . H
  O17 1.0267(3) 0.28210(11) 0.56658(14) 0.0193(5) Uani d . 1 . . O
  N21 1.2614(4) 0.18964(14) 0.50813(17) 0.0169(6) Uani d . 1 . . N
  C22 1.3864(5) 0.21944(17) 0.5804(2) 0.0170(8) Uani d . 1 . . C
  C23 1.5226(5) 0.18547(18) 0.6477(2) 0.0225(9) Uani d . 1 . . C
  H231 1.6132 0.2059 0.6978 0.027 Uiso calc R 1 . . H
  C24 1.5271(5) 0.12220(18) 0.6424(2) 0.0242(9) Uani d . 1 . . C
  H241 1.6182 0.0987 0.6892 0.029 Uiso calc R 1 . . H
  C25 1.3987(5) 0.09304(18) 0.5687(2) 0.0230(8) Uani d . 1 . . C
  H251 1.4008 0.0493 0.5644 0.028 Uiso calc R 1 . . H
  C26 1.2677(5) 0.12777(17) 0.5016(2) 0.0213(8) Uani d . 1 . . C
  H261 1.1811 0.1080 0.4503 0.026 Uiso calc R 1 . . H
  O27 1.1355(3) 0.22215(11) 0.44180(14) 0.0199(6) Uani d . 1 . . O
  N31 0.4211(4) 0.29046(14) 0.36616(17) 0.0179(7) Uani d . 1 . . N
  C32 0.2882(5) 0.26057(17) 0.2950(2) 0.0178(8) Uani d . 1 . . C
  C33 0.1381(5) 0.29506(19) 0.2311(2) 0.0228(9) Uani d . 1 . . C
  H331 0.0396 0.2749 0.1825 0.027 Uiso calc R 1 . . H
  C34 0.1319(5) 0.35817(19) 0.2380(2) 0.0281(9) Uani d . 1 . . C
  H341 0.0314 0.3817 0.1938 0.034 Uiso calc R 1 . . H
  C35 0.2727(5) 0.38725(19) 0.3097(2) 0.0281(9) Uani d . 1 . . C
  H351 0.2710 0.4309 0.3148 0.034 Uiso calc R 1 . . H
  C36 0.4154(5) 0.35222(17) 0.3738(2) 0.0227(8) Uani d . 1 . . C
  H361 0.5105 0.3718 0.4237 0.027 Uiso calc R 1 . . H
  O37 0.5542(3) 0.25760(11) 0.43090(14) 0.0191(5) Uani d . 1 . . O
  N51 0.8216(4) 0.16003(15) 0.48721(19) 0.0240(7) Uani d . 1 . . N
  C52 0.8226(5) 0.11017(19) 0.5107(2) 0.0210(8) Uani d . 1 . . C
  N53 0.8012(5) 0.05413(15) 0.5337(2) 0.0350(9) Uani d . 1 . . N
  C54 0.9621(6) 0.02392(18) 0.5886(3) 0.0286(9) Uani d . 1 . . C
  N55 1.0880(6) -0.00625(19) 0.6370(3) 0.0533(11) Uani d . 1 . . N
  N61 0.8607(4) 0.31964(15) 0.38200(18) 0.0221(7) Uani d . 1 . . N
  C62 0.8618(5) 0.37227(18) 0.3705(2) 0.0202(8) Uani d . 1 . . C
  N63 0.8372(4) 0.43000(15) 0.3488(2) 0.0321(8) Uani d . 1 . . N
  C64 0.9911(5) 0.46978(18) 0.3870(2) 0.0224(8) Uani d . 1 . . C
  N65 1.1151(5) 0.50820(16) 0.4155(2) 0.0362(9) Uani d . 1 . . N
  N41 0.4904(4) 0.16799(14) 0.29630(17) 0.0180(7) Uani d . 1 . . N
  C42 0.3018(5) 0.19322(17) 0.2907(2) 0.0186(8) Uani d . 1 . . C
  C43 0.1292(5) 0.15503(19) 0.2771(2) 0.0260(9) Uani d . 1 . . C
  H431 -0.0035 0.1726 0.2702 0.031 Uiso calc R 1 . . H
  C44 0.1487(6) 0.0923(2) 0.2736(2) 0.0299(10) Uani d . 1 . . C
  H441 0.0300 0.0662 0.2634 0.036 Uiso calc R 1 . . H
  C45 0.3459(6) 0.06740(19) 0.2852(2) 0.0320(10) Uani d . 1 . . C
  H451 0.3634 0.0239 0.2853 0.038 Uiso calc R 1 . . H
  C46 0.5149(6) 0.10573(18) 0.2966(2) 0.0262(9) Uani d . 1 . . C
  H461 0.6489 0.0886 0.3047 0.031 Uiso calc R 1 . . H
  O47 0.6505(3) 0.20413(11) 0.30105(13) 0.0200(6) Uani d . 1 . . O
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 0.0147(2) 0.0145(2) 0.0201(2) -0.00113(17) 0.00573(15) 0.00279(19)
  N11 0.0161(14) 0.0173(18) 0.0190(15) -0.0006(12) 0.0074(11) 0.0000(13)
  C12 0.0181(16) 0.018(2) 0.0156(18) -0.0002(14) 0.0056(13) -0.0011(15)
  C13 0.0224(17) 0.025(2) 0.0180(18) -0.0021(15) 0.0074(14) -0.0008(16)
  C14 0.0295(19) 0.025(3) 0.028(2) -0.0120(17) 0.0123(16) -0.0035(18)
  C15 0.037(2) 0.017(2) 0.026(2) -0.0034(17) 0.0101(16) 0.0010(17)
  C16 0.0265(18) 0.016(2) 0.024(2) 0.0045(16) 0.0083(15) -0.0003(17)
  O17 0.0175(11) 0.0186(15) 0.0230(13) -0.0036(10) 0.0093(10) 0.0002(11)
  N21 0.0139(13) 0.0182(19) 0.0198(16) 0.0011(12) 0.0078(11) 0.0027(13)
  C22 0.0149(16) 0.017(2) 0.0194(18) -0.0016(14) 0.0071(13) -0.0020(15)
  C23 0.0156(16) 0.026(3) 0.024(2) 0.0038(15) 0.0054(14) 0.0004(17)
  C24 0.0188(17) 0.023(2) 0.030(2) 0.0077(15) 0.0091(15) 0.0086(18)
  C25 0.0199(17) 0.015(2) 0.037(2) 0.0044(15) 0.0149(16) 0.0034(17)
  C26 0.0180(16) 0.019(2) 0.027(2) -0.0035(15) 0.0090(14) -0.0041(17)
  O27 0.0184(11) 0.0215(16) 0.0188(12) -0.0002(10) 0.0062(9) 0.0025(11)
  N31 0.0150(13) 0.0190(19) 0.0206(16) 0.0024(12) 0.0081(11) 0.0005(13)
  C32 0.0135(15) 0.019(2) 0.0238(19) 0.0010(14) 0.0105(13) -0.0002(16)
  C33 0.0169(16) 0.030(3) 0.0219(19) 0.0054(15) 0.0085(14) 0.0046(17)
  C34 0.0279(19) 0.032(3) 0.028(2) 0.0146(17) 0.0150(16) 0.0116(19)
  C35 0.035(2) 0.020(2) 0.038(2) 0.0085(17) 0.0231(18) 0.0031(19)
  C36 0.0230(17) 0.021(2) 0.028(2) 0.0002(15) 0.0135(15) -0.0043(17)
  O37 0.0171(11) 0.0222(15) 0.0163(12) 0.0011(10) 0.0047(9) 0.0037(11)
  N51 0.0158(14) 0.020(2) 0.0314(18) -0.0034(13) 0.0047(12) 0.0061(15)
  C52 0.0175(16) 0.024(2) 0.022(2) 0.0019(15) 0.0090(14) 0.0008(17)
  N53 0.0353(18) 0.018(2) 0.050(2) -0.0048(15) 0.0147(16) 0.0118(17)
  C54 0.043(2) 0.012(2) 0.044(3) -0.0062(18) 0.032(2) -0.0022(19)
  N55 0.049(2) 0.037(3) 0.081(3) 0.0129(19) 0.034(2) 0.030(2)
  N61 0.0187(14) 0.019(2) 0.0268(17) -0.0022(13) 0.0071(12) 0.0023(14)
  C62 0.0163(16) 0.021(2) 0.0210(19) -0.0025(15) 0.0050(14) 0.0016(17)
  N63 0.0288(16) 0.017(2) 0.041(2) -0.0004(14) 0.0037(14) 0.0044(16)
  C64 0.0277(18) 0.015(2) 0.030(2) 0.0046(17) 0.0177(16) 0.0073(17)
  N65 0.0370(19) 0.018(2) 0.060(2) -0.0001(15) 0.0251(17) 0.0024(18)
  N41 0.0223(14) 0.0158(18) 0.0139(15) -0.0008(12) 0.0049(11) 0.0005(13)
  C42 0.0200(16) 0.020(2) 0.0170(18) 0.0022(15) 0.0081(13) 0.0011(15)
  C43 0.0264(18) 0.029(3) 0.022(2) -0.0096(17) 0.0098(15) -0.0063(18)
  C44 0.035(2) 0.032(3) 0.023(2) -0.0161(18) 0.0111(16) -0.0037(18)
  C45 0.052(2) 0.016(2) 0.023(2) -0.0115(19) 0.0096(18) -0.0009(17)
  C46 0.034(2) 0.022(2) 0.0189(19) 0.0067(17) 0.0065(15) -0.0005(17)
  O47 0.0173(11) 0.0179(16) 0.0246(13) -0.0027(10) 0.0081(10) 0.0012(11)
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 N51 . 1.976(3) yes
  Cu1 N61 . 1.983(3) yes
  Cu1 O37 . 1.995(2) yes
  Cu1 O27 . 2.000(2) yes
  Cu1 O47 . 2.288(2) yes
  Cu1 O17 . 2.309(2) yes
  N11 O17 . 1.326(3) ?
  N11 C16 . 1.344(4) ?
  N11 C12 . 1.366(4) ?
  C12 C13 . 1.393(5) ?
  C12 C22 . 1.469(5) ?
  C13 C14 . 1.375(5) ?
  C13 H131 . 0.9500 ?
  C14 C15 . 1.389(5) ?
  C14 H141 . 0.9500 ?
  C15 C16 . 1.378(5) ?
  C15 H151 . 0.9500 ?
  C16 H161 . 0.9500 ?
  N21 O27 . 1.330(3) ?
  N21 C26 . 1.346(4) ?
  N21 C22 . 1.363(4) ?
  C22 C23 . 1.380(5) ?
  C23 C24 . 1.374(5) ?
  C23 H231 . 0.9500 ?
  C24 C25 . 1.380(5) ?
  C24 H241 . 0.9500 ?
  C25 C26 . 1.375(5) ?
  C25 H251 . 0.9500 ?
  C26 H261 . 0.9500 ?
  N31 O37 . 1.334(3) ?
  N31 C36 . 1.345(4) ?
  N31 C32 . 1.368(4) ?
  C32 C33 . 1.391(5) ?
  C32 C42 . 1.465(5) ?
  C33 C34 . 1.373(5) ?
  C33 H331 . 0.9500 ?
  C34 C35 . 1.383(5) ?
  C34 H341 . 0.9500 ?
  C35 C36 . 1.378(5) ?
  C35 H351 . 0.9500 ?
  C36 H361 . 0.9500 ?
  N51 C52 . 1.152(4) ?
  C52 N53 . 1.302(5) ?
  N53 C54 . 1.310(5) ?
  C54 N55 . 1.141(5) ?
  N61 C62 . 1.157(4) ?
  C62 N63 . 1.296(5) ?
  N63 C64 . 1.320(5) ?
  C64 N65 . 1.152(5) ?
  N41 O47 . 1.325(3) ?
  N41 C46 . 1.358(4) ?
  N41 C42 . 1.373(4) ?
  C42 C43 . 1.387(5) ?
  C43 C44 . 1.367(5) ?
  C43 H431 . 0.9500 ?
  C44 C45 . 1.397(5) ?
  C44 H441 . 0.9500 ?
  C45 C46 . 1.376(5) ?
  C45 H451 . 0.9500 ?
  C46 H461 . 0.9500 ?