data_2006368
_journal_name_full  'Acta Crystallographica'
_journal_year  1997
_journal_volume  C53
_journal_page_first  1058
_journal_page_last  1059
_publ_section_title
;
[N,N-Bis(2-chloroethyl)-1,2-ethylenediamine-N,N']bis(3-methyl-2,4-
pentanedionato-O,O')cobalt(III) Perchlorate: a Potential Hypoxia
Selective Anticancer Agent
;
loop_
_publ_author_name
 'Ware, David C.'
 'Denny, William A.'
 'Clark, George R.'
_chemical_formula_sum  'C18 H32 Cl3 Co N2 O8'
_chemical_formula_weight  569.74
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/c'
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  17.229(3)
_cell_length_b  10.817(5)
_cell_length_c  14.851(6)
_cell_angle_alpha  90.00
_cell_angle_beta  110.78(3)
_cell_angle_gamma  90.00
_cell_volume  2587.7(16)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.462
_diffrn_ambient_temperature  293(2)
_refine_ls_R_factor_obs   .0504
_refine_ls_wR_factor_obs   .1178
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
 Co  .21249(4)  .11234(6)  .23461(4)  .0406(2) Uani d . 1 . Co
 Cl1  .3990(2)  -.3271(2)  .2881(2)  .1428(11) Uani d . 1 . Cl
 Cl2A  .3956(8)  -.0129(8)  .066(2)  .163(7) Uani d P  .70(4) . Cl
 Cl2B  .3621(18)  -.014(2)  .0041(17)  .119(6) Uani d P  .30(4) . Cl
 Cl3  .92054(8)  .27263(12)  .12985(9)  .0521(3) Uani d . 1 . Cl
 O1  .1860(2)  .2505(3)  .2937(2)  .0500(9) Uani d . 1 . O
 O2  .1743(2)  .1838(3)  .1121(2)  .0480(9) Uani d . 1 . O
 O3  .2439(2)  .0340(3)  .3548(2)  .0469(8) Uani d . 1 . O
 O4  .3187(2)  .1783(4)  .2586(3)  .0587(10) Uani d . 1 . O
 O5  .9630(3)  .2296(4)  .2263(3)  .0803(13) Uani d . 1 . O
 O6  .9553(3)  .2091(5)  .0692(3)  .0843(14) Uani d . 1 . O
 O7  .9336(3)  .4020(4)  .1278(3)  .0782(13) Uani d . 1 . O
 O8  .8340(3)  .2471(4)  .1027(4)  .091(2) Uani d . 1 . O
 N1  .1020(3)  .0486(4)  .2093(3)  .0469(10) Uani d . 1 . N
 H1A  .0982(3)  .0176(4)  .2638(3)  .056 Uiso calc R 1 . H
 H1B  .0646(3)  .1099(4)  .1884(3)  .056 Uiso calc R 1 . H
 N2  .2359(3)  -.0507(4)  .1728(3)  .0449(10) Uani d . 1 . N
 C1  .1616(3)  .3557(5)  .2533(4)  .0465(12) Uani d . 1 . C
 C2  .1461(3)  .3865(5)  .1570(4)  .0487(12) Uani d . 1 . C
 C3  .1492(3)  .2953(5)  .0909(4)  .0477(12) Uani d . 1 . C
 C4  .1454(5)  .4479(5)  .3196(4)  .075(2) Uani d . 1 . C
 H4A  .1591(5)  .4122(5)  .3826(4)  .090 Uiso calc R 1 . H
 H4B  .0878(5)  .4707(5)  .2954(4)  .090 Uiso calc R 1 . H
 H4C  .1789(5)  .5201(5)  .3235(4)  .090 Uiso calc R 1 . H
 C5  .1169(4)  .5157(5)  .1232(4)  .069(2) Uani d . 1 . C
 H5A  .1089(4)  .5234(5)  .0561(4)  .083 Uiso calc R 1 . H
 H5B  .1577(4)  .5744(5)  .1596(4)  .083 Uiso calc R 1 . H
 H5C  .0653(4)  .5314(5)  .1324(4)  .083 Uiso calc R 1 . H
 C6  .1191(4)  .3213(5)  -.0156(4)  .067(2) Uani d . 1 . C
 H6A  .1260(4)  .2487(5)  -.0492(4)  .081 Uiso calc R 1 . H
 H6B  .1507(4)  .3880(5)  -.0279(4)  .081 Uiso calc R 1 . H
 H6C  .0615(4)  .3437(5)  -.0376(4)  .081 Uiso calc R 1 . H
 C7  .3088(4)  .0596(5)  .4280(4)  .0577(14) Uani d . 1 . C
 C8  .3715(4)  .1404(6)  .4279(4)  .068(2) Uani d . 1 . C
 C9  .3738(4)  .1917(6)  .3420(5)  .068(2) Uani d . 1 . C
 C10  .3122(5)  -.0091(7)  .5164(4)  .086(2) Uani d . 1 . C
 H10A  .2636(5)  -.0599(7)  .5023(4)  .103 Uiso calc R 1 . H
 H10B  .3143(5)  .0488(7)  .5663(4)  .103 Uiso calc R 1 . H
 H10C  .3608(5)  -.0603(7)  .5376(4)  .103 Uiso calc R 1 . H
 C11  .4428(5)  .1665(9)  .5218(5)  .109(3) Uani d . 1 . C
 H11A  .4808(5)  .2236(9)  .5101(5)  .131 Uiso calc R 1 . H
 H11B  .4712(5)  .0907(9)  .5470(5)  .131 Uiso calc R 1 . H
 H11C  .4213(5)  .2016(9)  .5675(5)  .131 Uiso calc R 1 . H
 C12  .4460(5)  .2730(10)  .3415(7)  .124(3) Uani d . 1 . C
 H12A  .4369(5)  .2995(10)  .2769(7)  .148 Uiso calc R 1 . H
 H12B  .4967(5)  .2267(10)  .3657(7)  .148 Uiso calc R 1 . H
 H12C  .4497(5)  .3440(10)  .3816(7)  .148 Uiso calc R 1 . H
 C13  .0846(3)  -.0489(5)  .1358(4)  .0521(13) Uani d . 1 . C
 H13A  .0725(3)  -.0126(5)  .0725(4)  .062 Uiso calc R 1 . H
 H13B  .0371(3)  -.0976(5)  .1350(4)  .062 Uiso calc R 1 . H
 C14  .1601(3)  -.1286(5)  .1610(4)  .0489(12) Uani d . 1 . C
 H14A  .1529(3)  -.1893(5)  .1106(4)  .059 Uiso calc R 1 . H
 H14B  .1677(3)  -.1725(5)  .2205(4)  .059 Uiso calc R 1 . H
 C15  .3100(4)  -.1174(6)  .2381(4)  .063(2) Uani d . 1 . C
 H15A  .3035(4)  -.1293(6)  .2998(4)  .075 Uiso calc R 1 . H
 H15B  .3586(4)  -.0659(6)  .2489(4)  .075 Uiso calc R 1 . H
 C16  .3255(5)  -.2435(7)  .2005(5)  .088(2) Uani d . 1 . C
 H16A  .3437(5)  -.2313(7)  .1465(5)  .105 Uiso calc R 1 . H
 H16B  .2739(5)  -.2898(7)  .1778(5)  .105 Uiso calc R 1 . H
 C17  .2393(4)  -.0312(5)  .0745(4)  .0587(15) Uani d . 1 . C
 H17A  .2470(4)  -.1110(5)  .0491(4)  .070 Uiso calc R 1 . H
 H17B  .1860(4)  .0005(5)  .0331(4)  .070 Uiso calc R 1 . H
 C18  .3053(5)  .0540(7)  .0679(5)  .084(2) Uani d . 1 . C
 H18A  .3425(5)  .0750(7)  .1323(5)  .101 Uiso calc R 1 . H
 H18B  .2799(5)  .1298(7)  .0361(5)  .101 Uiso calc R 1 . 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
 Co  .0525(4)  .0344(4)  .0354(4)  -.0004(3)  .0160(3)  -.0010(3)
 Cl1  .149(2)  .100(2)  .130(2)  .058(2)  -.010(2)  -.0142(15)
 Cl2A  .092(5)  .115(4)  .32(2) .036(3)  .117(9)  .046(6)
 Cl2B  .087(10)  .164(10)  .129(12)  .011(7)  .069(8)  -.013(8)
 Cl3  .0634(8)  .0403(7)  .0525(7)  .0066(6)  .0203(6)  -.0009(6)
 O1  .080(3)  .038(2)  .034(2)  .002(2)  .023(2)  -.0014(15)
 O2  .077(2)  .034(2)  .036(2)  .003(2)  .024(2)  -.0024(15)
 O3  .054(2)  .046(2)  .040(2)  .001(2)  .015(2)  .0034(15)
 O4  .062(2)  .063(2)  .053(2)  -.021(2)  .022(2)  -.012(2)
 O5  .107(4)  .078(3)  .055(2)  .015(3)  .027(2)  .010(2)
 O6  .091(3)  .094(3)  .065(3)  .024(3)  .025(2)  -.029(3)
 O7  .113(4)  .039(2)  .095(3)  -.004(2)  .052(3)  .006(2)
 O8  .062(3)  .072(3)  .128(4)  .001(2)  .018(3)  -.023(3)
 N1  .054(3)  .045(2)  .044(2)  .009(2)  .019(2)  .007(2)
 N2  .049(2)  .043(2)  .043(2)  -.001(2)  .016(2)  -.007(2)
 C1  .063(3)  .037(3)  .044(3)  -.012(2)  .023(2)  -.007(2)
 C2  .064(3)  .037(3)  .048(3)  .001(2)  .023(3)  .001(2)
 C3  .061(3)  .042(3)  .044(3)  -.004(2)  .024(2)  .005(2)
 C4  .127(6)  .047(3)  .056(3)  .012(4)  .038(4)  -.014(3)
 C5  .106(5)  .041(3)  .066(4)  .009(3)  .038(4)  .007(3)
 C6  .116(5)  .047(3)  .043(3)  .012(3)  .035(3)  .010(3)
 C7  .060(4)  .055(3)  .050(3)  .011(3)  .011(3)  -.004(3)
 C8  .063(4)  .074(4)  .055(4)  -.007(3)  .004(3)  -.020(3)
 C9  .061(4)  .072(4)  .075(4)  -.019(3)  .031(3)  -.031(3)
 C10  .088(5)  .110(6)  .045(3)  .001(4)  .007(3)  .016(4)
 C11  .093(6)  .134(8)  .075(5)  -.027(5)  -.002(4)  -.021(5)
 C12  .088(6)  .153(9)  .131(7)  -.066(6)  .040(5)  -.028(7)
 C13  .058(3)  .043(3)  .055(3)  -.005(2)  .019(3)  -.007(2)
 C14  .065(3)  .038(3)  .041(3)  -.006(2)  .015(2)  -.010(2)
 C15  .058(3)  .064(4)  .056(3)  .016(3)  .007(3)  -.015(3)
 C16  .089(5)  .075(5)  .086(5)  .029(4)  .013(4)  -.020(4)
 C17  .084(4)  .049(3)  .052(3)  -.007(3)  .035(3)  -.011(3)
 C18  .093(5)  .089(5)  .090(5)  -.007(4)  .058(4)  -.009(4)
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
 Co O2 . 1.868(3) ?
 Co O1 . 1.870(3) ?
 Co O3 . 1.874(3) ?
 Co O4 . 1.877(4) ?
 Co N1 . 1.931(4) ?
 Co N2 . 2.092(4) ?
 Cl1 C16 . 1.716(7) ?
 Cl2B C18 . 1.75(2) ?
 Cl3 O7 . 1.419(4) ?
 Cl3 O6 . 1.423(4) ?
 Cl3 O8 . 1.427(5) ?
 Cl3 O5 . 1.435(4) ?
 O1 C1 . 1.285(6) ?
 O2 C3 . 1.282(6) ?
 O3 C7 . 1.283(6) ?
 O4 C9 . 1.274(7) ?
 N1 C13 . 1.471(6) ?
 N2 C15 . 1.488(7) ?
 N2 C17 . 1.497(6) ?
 N2 C14 . 1.511(6) ?
 C1 C2 . 1.400(7) ?
 C1 C4 . 1.496(7) ?
 C2 C3 . 1.406(7) ?
 C2 C5 . 1.509(7) ?
 C3 C6 . 1.506(7) ?
 C7 C8 . 1.392(9) ?
 C7 C10 . 1.491(8) ?
 C8 C9 . 1.404(9) ?
 C8 C11 . 1.522(8) ?
 C9 C12 . 1.526(9) ?
 C13 C14 . 1.493(7) ?
 C15 C16 . 1.532(8) ?
 C17 C18 . 1.493(8) ?