#------------------------------------------------------------------------------
#$Date: 2009-11-16 01:43:51 +0000 (Mon, 16 Nov 2009) $
#$Revision: 853 $
#$URL: svn://www.crystallography.net/cod/cif/2/2007353.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_2007353
_journal_name_full 'Acta Crystallographica Section C'
_journal_year  1998
_journal_volume 54
_journal_page_first  773
_journal_page_last  776
_publ_section_title
;
  A Dinuclear Complex of the Thiopurine Drug Azathioprine:
  [Cu~2~Cl~4~(\m-azathioprine)~2~].4DMF
;
_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
  'Zhu, Fu-Chun'
  'Schmalle, Helmut W.'
  'Dubler, Erich'
_chemical_formula_moiety  'C9 H7 Cu1 Cl2 N7 O2 S1,2(C3 H7 N1 O1)'
_chemical_formula_sum  'C15 H21 Cl2 Cu N9 O4 S1'
_chemical_formula_iupac  '[Cu2 Cl4 (C9 H7 N7 O2 S)2] , 4C3 H7 NO'
_chemical_formula_weight  1115.82
_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  11.739(2)
_cell_length_b  10.092(2)
_cell_length_c  20.652(4)
_cell_angle_alpha  90.00
_cell_angle_beta  99.53(3)
_cell_angle_gamma  90.00
_cell_volume  2412.9(8)
_cell_formula_units_Z  2
_cell_measurement_temperature  296(2)
_exptl_crystal_density_diffrn  1.536
_diffrn_ambient_temperature  296(2)
_refine_ls_R_factor_obs  .0769
_refine_ls_wR_factor_obs  .1235
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
  Cu1  .39179(9)  .06299(11)  .01070(5)  .0375(3) Uani d . 1 . Cu
  S6  .5490(2)  -.1409(3)  .31333(10)  .0490(7) Uani d . 1 . S
  Cl1  .3834(2)  -.1566(2)  -.01560(10)  .0502(7) Uani d . 1 . Cl
  Cl2  .2996(2)  .2481(3)  .03243(11)  .0619(8) Uani d . 1 . Cl
  N1  .4091(6)  -.0099(7)  .2152(3)  .040(2) Uani d . 1 . N
  C2  .3854(8)  .0325(8)  .1535(4)  .038(2) Uani d . 1 . C
  N3  .4429(5)  .0114(6)  .1050(3)  .032(2) Uani d . 1 . N
  C4  .5408(7)  -.0582(9)  .1228(3)  .032(2) Uani d . 1 . C
  C5  .5763(7)  -.1054(8)  .1864(4)  .035(2) Uani d . 1 . C
  C6  .5069(7)  -.0809(8)  .2324(4)  .037(2) Uani d . 1 . C
  N7  .6774(6)  -.1736(7)  .1861(3)  .039(2) Uani d . 1 . N
  C8  .6987(8)  -.1679(9)  .1247(4)  .039(2) Uani d . 1 . C
  N9  .6184(5)  -.1012(6)  .0844(3)  .034(2) Uani d . 1 . N
  C10  .4200(8)  -.1164(9)  .3436(4)  .041(2) Uani d . 1 . C
  N11  .4123(6)  -.0200(7)  .3890(3)  .044(2) Uani d . 1 . N
  C16  .5004(8)  .0709(10)  .4171(5)  .067(3) Uani d . 1 . C
  H11A  .518(4)  .131(4)  .3838(8)  .101 Uiso calc R 1 . H
  H11B  .5688(19)  .0227(11)  .435(3)  .101 Uiso calc R 1 . H
  H11C  .474(2)  .121(4)  .451(2)  .101 Uiso calc R 1 . H
  C12  .3024(10)  -.0259(11)  .3998(5)  .053(3) Uani d . 1 . C
  N13  .2401(7)  -.1148(9)  .3674(4)  .064(3) Uani d . 1 . N
  C14  .3130(9)  -.1716(10)  .3311(5)  .055(3) Uani d . 1 . C
  N15  .2810(10)  -.2794(11)  .2876(6)  .090(3) Uani d . 1 . N
  O11  .3490(8)  -.3171(8)  .2522(5)  .100(3) Uani d . 1 . O
  O12  .1866(10)  -.3243(12)  .2847(6)  .174(6) Uani d . 1 . O
  H2  .320(5)  .088(6)  .143(3)  .006(17) Uiso d . 1 . H
  H7  .721(7)  -.208(9)  .224(4)  .07(3)  Uiso d . 1 . H
  H8  .758(5)  -.209(7)  .109(3)  .02(2)  Uiso d . 1 . H
  H12  .285(5)  .030(7)  .433(3)  .02(2)  Uiso d . 1 . H
  O1A  .1819(6)  .2248(7)  .2159(3)  .062(2) Uani d . 1 . O
  N3A  .0582(8)  .0539(11)  .1900(6)  .092(3) Uani d . 1 . N
  C2A  .1349(9)  .1235(12)  .2290(5)  .066(3) Uani d . 1 . C
  H2A  .1557(9)  .0917(12)  .2716(5)  .080 Uiso calc R 1 . H
  C4A  .0020(13)  -.0638(13)  .2126(8)  .159(7) Uani d . 1 . C
  H4A1  -.079(2)  -.062(6)  .195(5)  .238 Uiso calc R 1 . H
  H4A2  .012(9)  -.064(6)  .2597(8)  .238 Uiso calc R 1 . H
  H4A3  .036(7)  -.1423(13)  .198(5)  .238 Uiso calc R 1 . H
  C5A  .0151(12)  .1058(17)  .1256(6)  .149(7) Uani d . 1 . C
  H5A1  -.0675(15)  .113(11)  .120(2)  .224 Uiso calc R 1 . H
  H5A2  .036(9)  .047(6)  .0929(6)  .224 Uiso calc R 1 . H
  H5A3  .048(8)  .192(5)  .121(2)  .224 Uiso calc R 1 . H
  O1B  .9234(7)  .6691(8)  .1191(4)  .094(3) Uiso d . 1 . O
  N3B 1.0818(11)  .6249(13)  .0805(6)  .113(4) Uiso d . 1 . N
  C2B1  .969(2)  .680(2)  .0721(13)  .093(6) Uiso d P  .511(12) 1 C
  H2B1  .934(2)  .720(2)  .0334(13)  .111 Uiso calc PR  .511(12) 1 H
  C4B1 1.128(4)  .515(4)  .123(2)  .223(11) Uiso d P  .511(12) 1 C
  H4B1 1.207(4)  .499(4)  .119(2)  .334 Uiso calc PR  .511(12) 1 H
  H4B2 1.084(4)  .436(4)  .111(2)  .334 Uiso calc PR  .511(12) 1 H
  H4B3 1.124(4)  .537(4)  .168(2)  .334 Uiso calc PR  .511(12) 1 H
  C5B1 1.139(3)  .613(4)  .020(2)  .223(11) Uiso d P  .511(12) 1 C
  H5B1 1.215(3)  .576(4)  .032(2)  .334 Uiso calc PR  .511(12) 1 H
  H5B2 1.145(3)  .699(4)  .001(2)  .334 Uiso calc PR  .511(12) 1 H
  H5B3 1.093(3)  .557(4)  -.011(2)  .334 Uiso calc PR  .511(12) 1 H
  C2B2 1.010(2)  .609(3)  .1208(13)  .093(6) Uiso d P  .489(12) 2 C
  H2B2 1.028(2)  .545(3)  .1535(13)  .111 Uiso calc PR  .489(12) 2 H
  C4B2 1.193(4)  .588(5)  .096(2)  .223(11) Uiso d P  .489(12) 2 C
  H4BX 1.233(4)  .610(5)  .061(2)  .334 Uiso calc PR  .489(12) 2 H
  H4BY 1.197(4)  .494(5)  .104(2)  .334 Uiso calc PR  .489(12) 2 H
  H4BZ 1.228(4)  .634(5)  .135(2)  .334 Uiso calc PR  .489(12) 2 H
  C5B2 1.077(4)  .733(5)  .038(2)  .223(11) Uiso d P  .489(12) 2 C
  H5BX 1.138(4)  .726(5)  .012(2)  .334 Uiso calc PR  .489(12) 2 H
  H5BY 1.086(4)  .814(5)  .062(2)  .334 Uiso calc PR  .489(12) 2 H
  H5BZ 1.004(4)  .733(5)  .009(2)  .334 Uiso calc PR  .489(12) 2 H
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  .0474(7)  .0410(7)  .0255(5)  .0080(7)  .0100(5)  .0023(6)
  S6  .059(2)  .062(2)  .0276(12)  .0164(14)  .0116(11)  .0099(12)
  Cl1  .064(2)  .0430(15)  .0428(13)  -.0062(13)  .0063(12)  -.0003(11)
  Cl2  .087(2)  .062(2)  .0400(13)  .034(2)  .0190(13)  .0042(12)
  N1  .045(5)  .050(5)  .026(4)  .020(4)  .012(3)  .009(3)
  C2  .045(6)  .039(6)  .028(5)  .012(5)  -.001(4)  .002(4)
  N3  .033(4)  .044(5)  .022(4)  .013(3)  .010(3)  .004(3)
  C4  .042(5)  .036(5)  .020(4)  -.003(5)  .009(4)  -.002(4)
  C5  .037(5)  .038(5)  .029(5)  .000(4)  .008(4)  .001(4)
  C6  .043(5)  .040(6)  .030(5)  -.003(5)  .014(4)  -.002(4)
  N7  .042(5)  .054(5)  .020(4)  .012(4)  .003(3)  .002(4)
  C8  .039(6)  .042(6)  .038(5)  .009(5)  .009(5)  -.003(5)
  N9  .033(4)  .038(5)  .034(4)  .010(3)  .009(3)  -.002(3)
  C10  .062(7)  .036(5)  .028(5)  .010(5)  .016(5)  .006(4)
  N11  .047(5)  .046(5)  .040(4)  .007(4)  .013(4)  .004(4)
  C16  .072(7)  .063(8)  .066(7)  -.006(7)  .008(6)  -.021(6)
  C12  .056(8)  .061(8)  .047(7)  .016(6)  .021(6)  .001(6)
  N13  .056(6)  .070(7)  .068(6)  -.001(5)  .016(5)  .014(5)
  C14  .060(8)  .044(7)  .056(7)  -.003(6)  -.001(6)  .014(5)
  N15  .077(9)  .070(8)  .113(10)  -.014(7)  -.012(7)  -.005(7)
  O11  .097(7)  .079(7)  .114(8)  .006(5)  -.009(6)  -.036(5)
  O12  .124(9)  .178(12)  .219(13)  -.075(9)  .023(9)  -.070(10)
  O1A  .056(5)  .078(6)  .052(4)  -.021(4)  .004(4)  -.011(4)
  N3A  .062(6)  .094(8)  .116(9)  -.031(7)  .006(6)  -.047(8)
  C2A  .048(7)  .091(10)  .059(7)  .006(7)  .007(6)  -.012(7)
  C4A  .163(15)  .078(11)  .219(19)  -.058(11)  -.014(13)  -.029(12)
  C5A  .126(13)  .24(2)  .075(10)  -.032(13)  .004(9)  -.028(12)
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 N9 3_655 1.985(6) yes
  Cu1 N3 . 2.008(6) yes
  Cu1 Cl2 . 2.241(3) yes
  Cu1 Cl1 . 2.280(3) yes
  Cu1 Cu1 3_655 2.939(2) yes
  S6 C10 . 1.748(9) yes
  S6 C6 . 1.769(8) yes
  N1 C2 . 1.330(9) yes
  N1 C6 . 1.350(9) yes
  C2 N3 . 1.314(9) yes
  C2 H2 .  .95(5) ?
  N3 C4 . 1.345(9) yes
  C4 N9 . 1.374(9) yes
  C4 C5 . 1.395(10) yes
  C5 N7 . 1.372(10) yes
  C5 C6 . 1.373(10) yes
  N7 C8 . 1.333(10) yes
  C8 N9 . 1.332(10) yes
  N9 Cu1 3_655 1.985(6) ?
  C10 N11 . 1.365(10) yes
  C10 C14 . 1.360(12) yes
  N11 C12 . 1.347(11) yes
  N11 C16 . 1.431(10) yes
  C16 H11A .  .96 ?
  C16 H11B .  .96 ?
  C16 H11C .  .96 ?
  C12 N13 . 1.275(12) yes
  C12 H12 .  .92(6) ?
  N13 C14 . 1.353(12) yes
  C14 N15 . 1.421(14) yes
  N15 O12 . 1.190(12) yes
  N15 O11 . 1.228(12) yes
  O1A C2A . 1.214(11) ?
  N3A C2A . 1.308(12) ?
  N3A C5A . 1.441(15) ?
  N3A C4A . 1.472(15) ?
  C2A H2A .  .93 ?
  C4A H4A1 .  .96 ?
  C4A H4A2 .  .96 ?
  C4A H4A3 .  .96 ?
  C5A H5A1 .  .96 ?
  C5A H5A2 .  .96 ?
  C5A H5A3 .  .96 ?
  O1B C2B1 . 1.19(3) ?
  O1B C2B2 . 1.18(3) ?
  N3B C2B2 . 1.29(3) ?
  N3B C4B2 . 1.34(4) ?
  N3B C5B2 . 1.40(4) ?
  N3B C2B1 . 1.42(3) ?
  N3B C4B1 . 1.47(4) ?
  N3B C5B1 . 1.51(4) ?
  C2B1 H2B1 .  .93 ?
  C4B1 H4B1 .  .96 ?
  C4B1 H4B2 .  .96 ?
  C4B1 H4B3 .  .96 ?
  C5B1 H5B1 .  .96 ?
  C5B1 H5B2 .  .96 ?
  C5B1 H5B3 .  .96 ?
  C2B2 H2B2 .  .93 ?
  C4B2 H4BX .  .96 ?
  C4B2 H4BY .  .96 ?
  C4B2 H4BZ .  .96 ?
  C5B2 H5BX .  .96 ?
  C5B2 H5BY .  .96 ?
  C5B2 H5BZ .  .96 ?