Chloridobis(ethyl-enediamine-κN,N')(n-pentyl-amine-κN)cobalt(III) dichloride monhydrate.

The title complex, [CoCl(C(5)H(13)N)(C(2)H(8)N(2))(2)]Cl(2)·H(2)O, comprises one chloridobis(ethyl-enediamine)(n-pentyl-amine)cobalt(III) cation, two chloride counter-anions and a water mol-ecule. The Co(III) atom of the complex is hexa-coordinated by five N and one Cl atoms. The five N atoms are from two chelating ethyl-enediamine and one n-pentyl-amine ligands. Neighbouring cations and anions are connected by N-H⋯Cl and N-H⋯O hydrogen bonds to each other and also to the water mol-ecule.

Related literature

For the potential applications of metal–chelate complexes, see: Tweedy (1964 ▶); Kralova et al. (2004 ▶); Parekh et al. (2005 ▶); Rajevel et al. (2008 ▶). For cobalt(III) complexes, see: Bailer & Clapp (1945 ▶); Bailer & Rollinson (1946 ▶). For a related structure, see: Ou et al. (2007 ▶).

Experimental

Crystal data

[CoCl(C5H13N)(C2H8N2)2]Cl2·H2O

M = 390.67

Monoclinic,

a = 10.5214 (3) Å

b = 7.2294 (2) Å

c = 23.6225 (6) Å

β = 96.117 (2)°

V = 1786.58 (8) Å3

Z = 4

Mo Kα radiation

μ = 1.41 mm−1

T = 293 K

0.25 × 0.20 × 0.15 mm

Data collection

Bruker Kappa-APEX2 CCD diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.719, T max = 0.816

23262 measured reflections

5510 independent reflections

4506 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.090

S = 1.10

5510 reflections

181 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.52 e Å−3

Δρmin = −0.35 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809022764/bq2142sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022764/bq2142Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[CoCl(C5H13N)(C2H8N2)2]Cl2·H2O	F(000) = 824
Mr = 390.67	Dx = 1.452 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8809 reflections
a = 10.5214 (3) Å	θ = 2.9–30.6°
b = 7.2294 (2) Å	µ = 1.41 mm−1
c = 23.6225 (6) Å	T = 293 K
β = 96.117 (2)°	Prismatic, orange
V = 1786.58 (8) Å3	0.25 × 0.20 × 0.15 mm
Z = 4

Bruker Kappa-APEX2 CCD diffractometer	5510 independent reflections
Radiation source: fine-focus sealed tube	4506 reflections with I > 2σ(I)
graphite	Rint = 0.029
ω and φ scans	θmax = 30.7°, θmin = 1.7°
Absorption correction: multi-scan (Blessing, 1995)	h = −15→15
Tmin = 0.719, Tmax = 0.816	k = −8→10
23262 measured reflections	l = −33→33

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.090	w = 1/[σ2(Fo2) + (0.0497P)2 + 0.0821P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max = 0.006
5510 reflections	Δρmax = 0.52 e Å−3
181 parameters	Δρmin = −0.35 e Å−3
3 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0019 (6)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C1	0.6942 (2)	0.3891 (2)	0.95347 (8)	0.0391 (4)
H1A	0.6317	0.4750	0.9657	0.047*
H1B	0.7675	0.4592	0.9439	0.047*
C2	0.73406 (18)	0.2535 (2)	1.00007 (8)	0.0352 (4)
H2A	0.7846	0.3145	1.0314	0.042*
H2B	0.6597	0.1982	1.0143	0.042*
C3	0.95703 (17)	0.0374 (3)	0.84080 (8)	0.0387 (4)
H3A	1.0400	0.0913	0.8368	0.046*
H3B	0.9209	−0.0074	0.8038	0.046*
C4	0.96996 (17)	−0.1182 (3)	0.88299 (8)	0.0364 (4)
H4A	1.0107	−0.2237	0.8670	0.044*
H4B	1.0220	−0.0798	0.9173	0.044*
C5	0.52205 (16)	0.0781 (2)	0.80180 (8)	0.0328 (4)
H5A	0.5349	0.2092	0.7957	0.039*
H5B	0.4656	0.0653	0.8315	0.039*
C6	0.45868 (16)	−0.0068 (3)	0.74740 (7)	0.0337 (4)
H6A	0.4451	−0.1377	0.7535	0.040*
H6B	0.5152	0.0053	0.7177	0.040*
C7	0.33189 (17)	0.0838 (3)	0.72777 (8)	0.0384 (4)
H7A	0.3453	0.2155	0.7234	0.046*
H7B	0.2745	0.0673	0.7569	0.046*
C8	0.26886 (18)	0.0065 (3)	0.67194 (8)	0.0393 (4)
H8A	0.3279	0.0169	0.6433	0.047*
H8B	0.2510	−0.1238	0.6769	0.047*
C9	0.1464 (2)	0.1043 (4)	0.65112 (12)	0.0659 (7)
H9A	0.1108	0.0501	0.6158	0.099*
H9B	0.1636	0.2329	0.6453	0.099*
H9C	0.0867	0.0922	0.6789	0.099*
N1	0.63802 (13)	0.28252 (18)	0.90348 (6)	0.0277 (3)
H1C	0.6409	0.3501	0.8717	0.033*
H1D	0.5556	0.2567	0.9072	0.033*
N2	0.81072 (13)	0.11089 (18)	0.97448 (5)	0.0262 (3)
H2C	0.8144	0.0081	0.9961	0.031*
H2D	0.8910	0.1525	0.9731	0.031*
N3	0.87124 (13)	0.1775 (2)	0.86270 (6)	0.0304 (3)
H3C	0.8378	0.2501	0.8339	0.036*
H3D	0.9161	0.2495	0.8887	0.036*
N4	0.84066 (13)	−0.16872 (19)	0.89632 (6)	0.0287 (3)
H4C	0.8457	−0.2249	0.9305	0.034*
H4D	0.8052	−0.2485	0.8700	0.034*
N5	0.64631 (13)	−0.0082 (2)	0.82114 (6)	0.0280 (3)
H5C	0.7005	0.0201	0.7954	0.034*
H5D	0.6350	−0.1316	0.8197	0.034*
O1	0.3655 (2)	0.2049 (5)	0.92521 (12)	0.1255 (12)
Cl1	0.58524 (4)	−0.11512 (6)	0.935779 (18)	0.03265 (10)
Cl2	1.09085 (4)	0.29130 (6)	0.96604 (2)	0.03712 (11)
Cl3	0.71601 (4)	0.54255 (6)	0.799916 (18)	0.03417 (10)
Co1	0.733516 (18)	0.05224 (3)	0.897435 (8)	0.02096 (7)
H1E	0.2883 (17)	0.237 (6)	0.9277 (18)	0.17 (2)*
H1F	0.394 (3)	0.137 (4)	0.9526 (11)	0.112 (13)*

	U11	U22	U33	U12	U13	U23
C1	0.0500 (11)	0.0276 (8)	0.0377 (10)	0.0041 (7)	−0.0040 (8)	−0.0063 (7)
C2	0.0430 (10)	0.0363 (9)	0.0258 (8)	0.0007 (7)	0.0007 (7)	−0.0091 (7)
C3	0.0290 (8)	0.0591 (12)	0.0287 (9)	0.0046 (8)	0.0069 (7)	−0.0004 (8)
C4	0.0280 (8)	0.0435 (10)	0.0368 (10)	0.0095 (7)	−0.0005 (7)	−0.0062 (8)
C5	0.0286 (8)	0.0373 (9)	0.0305 (9)	0.0047 (6)	−0.0068 (6)	−0.0044 (7)
C6	0.0306 (8)	0.0408 (9)	0.0279 (9)	0.0023 (7)	−0.0056 (6)	−0.0024 (7)
C7	0.0321 (9)	0.0480 (10)	0.0328 (10)	0.0057 (7)	−0.0068 (7)	−0.0062 (8)
C8	0.0350 (9)	0.0469 (10)	0.0331 (10)	0.0021 (8)	−0.0097 (7)	−0.0036 (8)
C9	0.0468 (13)	0.0812 (17)	0.0632 (16)	0.0152 (12)	−0.0241 (11)	−0.0116 (13)
N1	0.0287 (7)	0.0261 (6)	0.0278 (7)	0.0018 (5)	0.0005 (5)	0.0014 (5)
N2	0.0274 (6)	0.0286 (6)	0.0218 (6)	−0.0027 (5)	−0.0017 (5)	−0.0002 (5)
N3	0.0264 (6)	0.0369 (7)	0.0274 (7)	−0.0017 (5)	0.0017 (5)	0.0070 (6)
N4	0.0313 (7)	0.0283 (6)	0.0250 (7)	0.0035 (5)	−0.0037 (5)	−0.0030 (5)
N5	0.0276 (6)	0.0345 (7)	0.0208 (6)	0.0030 (5)	−0.0032 (5)	−0.0009 (5)
O1	0.0775 (15)	0.188 (3)	0.121 (2)	0.0730 (17)	0.0573 (15)	0.104 (2)
Cl1	0.0302 (2)	0.0344 (2)	0.0332 (2)	−0.00734 (15)	0.00280 (15)	0.00406 (16)
Cl2	0.0307 (2)	0.0406 (2)	0.0387 (2)	−0.00616 (16)	−0.00247 (16)	0.00198 (18)
Cl3	0.0438 (2)	0.0327 (2)	0.0259 (2)	−0.00019 (16)	0.00328 (16)	−0.00105 (15)
Co1	0.02095 (11)	0.02308 (11)	0.01830 (11)	−0.00082 (7)	−0.00051 (7)	0.00072 (7)

C1—N1	1.479 (2)	C8—C9	1.505 (3)
C1—C2	1.501 (3)	C8—H8A	0.9700
C1—H1A	0.9700	C8—H8B	0.9700
C1—H1B	0.9700	C9—H9A	0.9600
C2—N2	1.477 (2)	C9—H9B	0.9600
C2—H2A	0.9700	C9—H9C	0.9600
C2—H2B	0.9700	N1—Co1	1.9575 (13)
C3—N3	1.485 (2)	N1—H1C	0.9000
C3—C4	1.500 (3)	N1—H1D	0.9000
C3—H3A	0.9700	N2—Co1	1.9588 (13)
C3—H3B	0.9700	N2—H2C	0.9000
C4—N4	1.475 (2)	N2—H2D	0.9000
C4—H4A	0.9700	N3—Co1	1.9611 (13)
C4—H4B	0.9700	N3—H3C	0.9000
C5—N5	1.477 (2)	N3—H3D	0.9000
C5—C6	1.513 (2)	N4—Co1	1.9569 (13)
C5—H5A	0.9700	N4—H4C	0.9000
C5—H5B	0.9700	N4—H4D	0.9000
C6—C7	1.514 (2)	N5—Co1	1.9822 (13)
C6—H6A	0.9700	N5—H5C	0.9000
C6—H6B	0.9700	N5—H5D	0.9000
C7—C8	1.518 (2)	O1—H1E	0.852 (10)
C7—H7A	0.9700	O1—H1F	0.841 (10)
C7—H7B	0.9700	Cl1—Co1	2.2403 (4)
N1—C1—C2	107.56 (14)	H9A—C9—H9B	109.5
N1—C1—H1A	110.2	C8—C9—H9C	109.5
C2—C1—H1A	110.2	H9A—C9—H9C	109.5
N1—C1—H1B	110.2	H9B—C9—H9C	109.5
C2—C1—H1B	110.2	C1—N1—Co1	109.70 (11)
H1A—C1—H1B	108.5	C1—N1—H1C	109.7
N2—C2—C1	106.15 (14)	Co1—N1—H1C	109.7
N2—C2—H2A	110.5	C1—N1—H1D	109.7
C1—C2—H2A	110.5	Co1—N1—H1D	109.7
N2—C2—H2B	110.5	H1C—N1—H1D	108.2
C1—C2—H2B	110.5	C2—N2—Co1	109.93 (10)
H2A—C2—H2B	108.7	C2—N2—H2C	109.7
N3—C3—C4	107.18 (14)	Co1—N2—H2C	109.7
N3—C3—H3A	110.3	C2—N2—H2D	109.7
C4—C3—H3A	110.3	Co1—N2—H2D	109.7
N3—C3—H3B	110.3	H2C—N2—H2D	108.2
C4—C3—H3B	110.3	C3—N3—Co1	109.55 (11)
H3A—C3—H3B	108.5	C3—N3—H3C	109.8
N4—C4—C3	107.89 (14)	Co1—N3—H3C	109.8
N4—C4—H4A	110.1	C3—N3—H3D	109.8
C3—C4—H4A	110.1	Co1—N3—H3D	109.8
N4—C4—H4B	110.1	H3C—N3—H3D	108.2
C3—C4—H4B	110.1	C4—N4—Co1	110.28 (11)
H4A—C4—H4B	108.4	C4—N4—H4C	109.6
N5—C5—C6	112.74 (14)	Co1—N4—H4C	109.6
N5—C5—H5A	109.0	C4—N4—H4D	109.6
C6—C5—H5A	109.0	Co1—N4—H4D	109.6
N5—C5—H5B	109.0	H4C—N4—H4D	108.1
C6—C5—H5B	109.0	C5—N5—Co1	119.79 (10)
H5A—C5—H5B	107.8	C5—N5—H5C	107.4
C5—C6—C7	112.26 (15)	Co1—N5—H5C	107.4
C5—C6—H6A	109.2	C5—N5—H5D	107.4
C7—C6—H6A	109.2	Co1—N5—H5D	107.4
C5—C6—H6B	109.2	H5C—N5—H5D	106.9
C7—C6—H6B	109.2	H1E—O1—H1F	111.3 (17)
H6A—C6—H6B	107.9	N4—Co1—N1	174.92 (6)
C6—C7—C8	113.34 (15)	N4—Co1—N2	90.39 (6)
C6—C7—H7A	108.9	N1—Co1—N2	85.03 (6)
C8—C7—H7A	108.9	N4—Co1—N3	85.34 (6)
C6—C7—H7B	108.9	N1—Co1—N3	92.63 (6)
C8—C7—H7B	108.9	N2—Co1—N3	92.13 (6)
H7A—C7—H7B	107.7	N4—Co1—N5	91.10 (6)
C9—C8—C7	112.99 (18)	N1—Co1—N5	93.59 (6)
C9—C8—H8A	109.0	N2—Co1—N5	176.89 (6)
C7—C8—H8A	109.0	N3—Co1—N5	90.71 (6)
C9—C8—H8B	109.0	N4—Co1—Cl1	89.52 (4)
C7—C8—H8B	109.0	N1—Co1—Cl1	92.57 (4)
H8A—C8—H8B	107.8	N2—Co1—Cl1	88.79 (4)
C8—C9—H9A	109.5	N3—Co1—Cl1	174.78 (4)
C8—C9—H9B	109.5	N5—Co1—Cl1	88.49 (4)
N1—C1—C2—N2	50.28 (19)	C1—N1—Co1—N3	−79.47 (12)
N3—C3—C4—N4	48.28 (19)	C1—N1—Co1—N5	−170.35 (12)
N5—C5—C6—C7	−179.58 (16)	C1—N1—Co1—Cl1	101.00 (11)
C5—C6—C7—C8	177.60 (17)	C2—N2—Co1—N4	−166.25 (11)
C6—C7—C8—C9	−176.9 (2)	C2—N2—Co1—N1	15.94 (11)
C2—C1—N1—Co1	−37.75 (17)	C2—N2—Co1—N3	108.40 (11)
C1—C2—N2—Co1	−40.09 (16)	C2—N2—Co1—Cl1	−76.74 (10)
C4—C3—N3—Co1	−38.51 (17)	C3—N3—Co1—N4	15.27 (11)
C3—C4—N4—Co1	−36.06 (16)	C3—N3—Co1—N1	−169.40 (11)
C6—C5—N5—Co1	−170.27 (12)	C3—N3—Co1—N2	105.48 (11)
C4—N4—Co1—N2	−80.28 (11)	C3—N3—Co1—N5	−75.78 (12)
C4—N4—Co1—N3	11.82 (11)	C5—N5—Co1—N4	161.69 (13)
C4—N4—Co1—N5	102.45 (11)	C5—N5—Co1—N1	−20.28 (13)
C4—N4—Co1—Cl1	−169.07 (11)	C5—N5—Co1—N3	−112.95 (13)
C1—N1—Co1—N2	12.44 (12)	C5—N5—Co1—Cl1	72.21 (12)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···Cl3	0.90	2.39	3.2589 (14)	162
N1—H1D···O1	0.90	2.12	3.018 (3)	174
N3—H3C···Cl3	0.90	2.56	3.3641 (14)	150
N4—H4D···Cl3i	0.90	2.36	3.2597 (14)	179
N4—H4C···Cl2ii	0.90	2.51	3.3731 (15)	161
N5—H5C···Cl3iii	0.90	2.51	3.3605 (15)	158
N5—H5D···Cl3i	0.90	2.56	3.3784 (15)	151
C3—H3B···Cl3iii	0.97	2.73	3.616 (2)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1C⋯Cl3	0.90	2.39	3.2589 (14)	162
N1—H1D⋯O1	0.90	2.12	3.018 (3)	174
N3—H3C⋯Cl3	0.90	2.56	3.3641 (14)	150
N4—H4D⋯Cl3i	0.90	2.36	3.2597 (14)	179
N4—H4C⋯Cl2ii	0.90	2.51	3.3731 (15)	161
N5—H5C⋯Cl3iii	0.90	2.51	3.3605 (15)	158
N5—H5D⋯Cl3i	0.90	2.56	3.3784 (15)	151

Symmetry codes: (i) ; (ii) ; (iii) .