Chloridobis(ethane-1,2-diamine)(4-methyl-aniline)cobalt(III) dichloride monohydrate.

In the title compound, [CoCl(C(2)H(8)N(2))(2)(C(7)H(9)N)]Cl(2)·H(2)O, the Co(III) ion has a distorted octa-hedral coordination environment and is surrounded by four N atoms in an equatorial plane, with the other N and Cl atoms occupying the axial positions. The crystal packing is stabilized by N-H⋯O, N-H⋯Cl and O-H⋯Cl inter-actions.

Related literature

For the biological activity and potential applications of mixed ligand cobalt(III) complexes, see: Arslan et al. (2009 ▶); Delehanty et al. (2008 ▶); Sayed et al. (1992 ▶); Teicher et al. (1990 ▶). For Co—N and Co—Cl bond lengths in related complexes, see: Anbalagan et al. (2009 ▶); Lee et al. (2007 ▶); Ramesh et al. (2008 ▶); Ravichandran et al. (2009 ▶). For the preparation of dichloro­bis(1,2-diamino­ethane)cobalt(III) chloride, see: Bailer & Clapp (1945 ▶). For asymmetry parameters, see: Nardelli (1983 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

[CoCl(C2H8N2)2(C7H9N)]Cl2·H2O

M = 410.66

Triclinic,

a = 7.3796 (2) Å

b = 10.8367 (3) Å

c = 12.1789 (3) Å

α = 75.201 (1)°

β = 74.671 (2)°

γ = 78.862 (1)°

V = 899.86 (4) Å3

Z = 2

Mo Kα radiation

μ = 1.40 mm−1

T = 293 K

0.20 × 0.20 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.767, T max = 0.817

27923 measured reflections

8633 independent reflections

6851 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.091

S = 1.10

8633 reflections

239 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.50 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809043323/bt5082sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043323/bt5082Isup2.hkl

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

[CoCl(C2H8N2)2(C7H9N)]Cl2·H2O	Z = 2
Mr = 410.66	F(000) = 428
Triclinic, P1	Dx = 1.516 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3796 (2) Å	Cell parameters from 5716 reflections
b = 10.8367 (3) Å	θ = 2.4–32.8°
c = 12.1789 (3) Å	µ = 1.40 mm−1
α = 75.201 (1)°	T = 293 K
β = 74.671 (2)°	Block, red
γ = 78.862 (1)°	0.20 × 0.20 × 0.15 mm
V = 899.86 (4) Å3

Bruker Kappa APEXII CCD diffractometer	8633 independent reflections
Radiation source: fine-focus sealed tube	6851 reflections with I > 2σ(I)
graphite	Rint = 0.025
ω and φ scans	θmax = 37.6°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −11→11
Tmin = 0.767, Tmax = 0.817	k = −18→18
27923 measured reflections	l = −20→20

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ2(Fo2) + (0.0444P)2 + 0.0729P] where P = (Fo2 + 2Fc2)/3
8633 reflections	(Δ/σ)max < 0.001
239 parameters	Δρmax = 0.50 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

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
Cl1	0.22560 (5)	0.10374 (4)	0.37990 (3)	0.03929 (8)
Cl2	−0.29764 (4)	0.01499 (3)	0.10024 (3)	0.03307 (7)
Cl3	0.25518 (5)	0.52141 (3)	0.17368 (3)	0.03977 (8)
Co1	0.11254 (2)	0.140646 (14)	0.218880 (12)	0.02132 (4)
O1	−0.30863 (18)	0.39142 (13)	0.09756 (12)	0.0472 (3)
H1W	−0.287 (3)	0.415 (2)	0.029 (2)	0.061 (7)*
H2W	−0.408 (4)	0.424 (2)	0.122 (2)	0.061 (7)*
N1	0.32886 (14)	0.23025 (10)	0.13118 (9)	0.02693 (18)
H1A	0.319 (3)	0.3017 (19)	0.1556 (17)	0.047 (5)*
H1B	0.435 (2)	0.1842 (16)	0.1437 (14)	0.031 (4)*
C2	0.33739 (18)	0.26181 (12)	0.00430 (11)	0.0304 (2)
H2A	0.4046	0.1897	−0.0302	0.036*
H2B	0.4031	0.3362	−0.0337	0.036*
C3	0.13641 (18)	0.29018 (12)	−0.01003 (10)	0.0305 (2)
H3A	0.0761	0.3714	0.0109	0.037*
H3B	0.1334	0.2954	−0.0902	0.037*
N4	0.03717 (15)	0.18257 (11)	0.06885 (8)	0.02559 (18)
H4A	−0.075 (3)	0.1988 (15)	0.0745 (14)	0.028 (4)*
H4B	0.065 (2)	0.1235 (17)	0.0370 (15)	0.033 (4)*
N5	0.25627 (16)	−0.02271 (11)	0.18526 (11)	0.0299 (2)
H5A	0.325 (3)	−0.043 (2)	0.2275 (18)	0.051 (6)*
H5B	0.319 (3)	−0.0173 (19)	0.1170 (18)	0.045 (5)*
C6	0.1287 (2)	−0.12166 (12)	0.21421 (12)	0.0336 (2)
H6A	0.1999	−0.2072	0.2270	0.040*
H6B	0.0666	−0.1125	0.1511	0.040*
C7	−0.0154 (2)	−0.10131 (13)	0.32353 (13)	0.0383 (3)
H7A	−0.1160	−0.1536	0.3392	0.046*
H7B	0.0437	−0.1251	0.3896	0.046*
N8	−0.09254 (16)	0.03689 (11)	0.30385 (10)	0.02891 (19)
H8A	−0.146 (3)	0.0534 (18)	0.3710 (18)	0.047 (5)*
H8B	−0.177 (3)	0.0465 (18)	0.2693 (17)	0.043 (5)*
N9	−0.04520 (15)	0.30641 (10)	0.25264 (9)	0.02624 (18)
H9A	0.032 (3)	0.3621 (19)	0.2425 (17)	0.045 (5)*
H9B	−0.113 (2)	0.3357 (15)	0.2038 (14)	0.028 (4)*
C10	−0.17753 (17)	0.31173 (11)	0.36291 (10)	0.0269 (2)
C11	−0.35600 (19)	0.27735 (14)	0.38350 (12)	0.0352 (3)
H11	−0.3898	0.2479	0.3273	0.042*
C12	−0.4850 (2)	0.28674 (16)	0.48792 (13)	0.0411 (3)
H12	−0.6044	0.2621	0.5017	0.049*
C13	−0.4384 (2)	0.33237 (14)	0.57219 (11)	0.0382 (3)
C14	−0.2609 (2)	0.36910 (13)	0.54924 (11)	0.0370 (3)
H14	−0.2289	0.4018	0.6041	0.044*
C15	−0.12911 (19)	0.35829 (13)	0.44591 (11)	0.0320 (2)
H15	−0.0093	0.3821	0.4324	0.038*
C16	−0.5802 (3)	0.34315 (19)	0.68492 (14)	0.0541 (4)
H16A	−0.5368	0.3933	0.7250	0.081*
H16B	−0.5937	0.2587	0.7330	0.081*
H16C	−0.7005	0.3844	0.6686	0.081*

	U11	U22	U33	U12	U13	U23
Cl1	0.04434 (18)	0.04594 (18)	0.03245 (15)	−0.00318 (14)	−0.01775 (13)	−0.00983 (13)
Cl2	0.02439 (13)	0.03889 (16)	0.03991 (15)	−0.00327 (11)	−0.00643 (11)	−0.01715 (13)
Cl3	0.04419 (18)	0.03590 (16)	0.04088 (17)	−0.01063 (13)	−0.00336 (13)	−0.01388 (13)
Co1	0.02056 (7)	0.02343 (7)	0.02069 (7)	−0.00416 (5)	−0.00377 (5)	−0.00610 (5)
O1	0.0374 (6)	0.0573 (7)	0.0410 (6)	0.0044 (5)	−0.0122 (5)	−0.0047 (5)
N1	0.0222 (4)	0.0276 (5)	0.0325 (5)	−0.0052 (4)	−0.0036 (4)	−0.0106 (4)
C2	0.0274 (5)	0.0302 (6)	0.0301 (5)	−0.0087 (4)	0.0021 (4)	−0.0057 (4)
C3	0.0310 (6)	0.0320 (6)	0.0246 (5)	−0.0060 (5)	−0.0022 (4)	−0.0018 (4)
N4	0.0240 (4)	0.0301 (5)	0.0236 (4)	−0.0064 (4)	−0.0034 (3)	−0.0075 (4)
N5	0.0272 (5)	0.0278 (5)	0.0347 (5)	−0.0025 (4)	−0.0055 (4)	−0.0094 (4)
C6	0.0392 (7)	0.0252 (5)	0.0365 (6)	−0.0066 (5)	−0.0068 (5)	−0.0068 (5)
C7	0.0456 (7)	0.0292 (6)	0.0343 (6)	−0.0101 (5)	−0.0008 (5)	−0.0012 (5)
N8	0.0285 (5)	0.0319 (5)	0.0253 (4)	−0.0084 (4)	−0.0011 (4)	−0.0064 (4)
N9	0.0258 (4)	0.0286 (5)	0.0235 (4)	−0.0034 (4)	−0.0022 (3)	−0.0078 (4)
C10	0.0276 (5)	0.0274 (5)	0.0245 (5)	−0.0015 (4)	−0.0029 (4)	−0.0081 (4)
C11	0.0319 (6)	0.0441 (7)	0.0317 (6)	−0.0065 (5)	−0.0021 (5)	−0.0161 (5)
C12	0.0330 (6)	0.0486 (8)	0.0384 (7)	−0.0093 (6)	0.0045 (5)	−0.0139 (6)
C13	0.0453 (8)	0.0352 (7)	0.0258 (5)	0.0013 (6)	0.0020 (5)	−0.0075 (5)
C14	0.0499 (8)	0.0350 (6)	0.0262 (5)	0.0001 (6)	−0.0087 (5)	−0.0111 (5)
C15	0.0355 (6)	0.0333 (6)	0.0295 (5)	−0.0036 (5)	−0.0085 (5)	−0.0104 (5)
C16	0.0601 (10)	0.0575 (10)	0.0318 (7)	0.0018 (8)	0.0083 (7)	−0.0135 (7)

Cl1—Co1	2.2444 (3)	C6—H6B	0.9700
Co1—N1	1.9493 (10)	C7—N8	1.4777 (18)
Co1—N5	1.9600 (11)	C7—H7A	0.9700
Co1—N8	1.9648 (11)	C7—H7B	0.9700
Co1—N4	1.9673 (10)	N8—H8A	0.86 (2)
Co1—N9	2.0167 (10)	N8—H8B	0.82 (2)
O1—H1W	0.79 (3)	N9—C10	1.4439 (15)
O1—H2W	0.77 (3)	N9—H9A	0.87 (2)
N1—C2	1.4818 (17)	N9—H9B	0.841 (17)
N1—H1A	0.88 (2)	C10—C11	1.3797 (18)
N1—H1B	0.873 (17)	C10—C15	1.3876 (16)
C2—C3	1.5027 (18)	C11—C12	1.3866 (19)
C2—H2A	0.9700	C11—H11	0.9300
C2—H2B	0.9700	C12—C13	1.388 (2)
C3—N4	1.4849 (16)	C12—H12	0.9300
C3—H3A	0.9700	C13—C14	1.379 (2)
C3—H3B	0.9700	C13—C16	1.506 (2)
N4—H4A	0.801 (17)	C14—C15	1.3883 (19)
N4—H4B	0.797 (17)	C14—H14	0.9300
N5—C6	1.4768 (17)	C15—H15	0.9300
N5—H5A	0.78 (2)	C16—H16A	0.9600
N5—H5B	0.83 (2)	C16—H16B	0.9600
C6—C7	1.505 (2)	C16—H16C	0.9600
C6—H6A	0.9700
N1—Co1—N5	90.39 (5)	N5—C6—H6A	110.4
N1—Co1—N8	175.15 (5)	C7—C6—H6A	110.4
N5—Co1—N8	84.75 (5)	N5—C6—H6B	110.4
N1—Co1—N4	84.77 (4)	C7—C6—H6B	110.4
N5—Co1—N4	90.54 (5)	H6A—C6—H6B	108.6
N8—Co1—N4	95.17 (4)	N8—C7—C6	106.93 (11)
N1—Co1—N9	91.51 (4)	N8—C7—H7A	110.3
N5—Co1—N9	177.58 (4)	C6—C7—H7A	110.3
N8—Co1—N9	93.34 (4)	N8—C7—H7B	110.3
N4—Co1—N9	88.15 (4)	C6—C7—H7B	110.3
N1—Co1—Cl1	89.09 (3)	H7A—C7—H7B	108.6
N5—Co1—Cl1	89.51 (4)	C7—N8—Co1	109.73 (9)
N8—Co1—Cl1	90.95 (4)	C7—N8—H8A	106.8 (13)
N4—Co1—Cl1	173.86 (3)	Co1—N8—H8A	112.7 (13)
N9—Co1—Cl1	92.01 (3)	C7—N8—H8B	107.1 (13)
H1W—O1—H2W	108 (2)	Co1—N8—H8B	113.5 (13)
C2—N1—Co1	111.40 (7)	H8A—N8—H8B	106.6 (18)
C2—N1—H1A	109.7 (13)	C10—N9—Co1	122.01 (8)
Co1—N1—H1A	108.8 (13)	C10—N9—H9A	106.4 (13)
C2—N1—H1B	108.9 (11)	Co1—N9—H9A	107.7 (13)
Co1—N1—H1B	111.2 (11)	C10—N9—H9B	103.3 (11)
H1A—N1—H1B	106.7 (17)	Co1—N9—H9B	109.0 (11)
N1—C2—C3	107.07 (10)	H9A—N9—H9B	107.5 (16)
N1—C2—H2A	110.3	C11—C10—C15	119.80 (11)
C3—C2—H2A	110.3	C11—C10—N9	120.15 (11)
N1—C2—H2B	110.3	C15—C10—N9	119.95 (11)
C3—C2—H2B	110.3	C10—C11—C12	120.01 (12)
H2A—C2—H2B	108.6	C10—C11—H11	120.0
N4—C3—C2	106.54 (10)	C12—C11—H11	120.0
N4—C3—H3A	110.4	C11—C12—C13	120.90 (14)
C2—C3—H3A	110.4	C11—C12—H12	119.6
N4—C3—H3B	110.4	C13—C12—H12	119.6
C2—C3—H3B	110.4	C14—C13—C12	118.40 (12)
H3A—C3—H3B	108.6	C14—C13—C16	121.16 (14)
C3—N4—Co1	108.95 (7)	C12—C13—C16	120.43 (15)
C3—N4—H4A	111.1 (12)	C13—C14—C15	121.37 (12)
Co1—N4—H4A	113.9 (11)	C13—C14—H14	119.3
C3—N4—H4B	107.5 (12)	C15—C14—H14	119.3
Co1—N4—H4B	112.7 (12)	C10—C15—C14	119.49 (13)
H4A—N4—H4B	102.4 (16)	C10—C15—H15	120.3
C6—N5—Co1	110.44 (8)	C14—C15—H15	120.3
C6—N5—H5A	108.2 (15)	C13—C16—H16A	109.5
Co1—N5—H5A	104.6 (15)	C13—C16—H16B	109.5
C6—N5—H5B	109.6 (13)	H16A—C16—H16B	109.5
Co1—N5—H5B	114.2 (13)	C13—C16—H16C	109.5
H5A—N5—H5B	110 (2)	H16A—C16—H16C	109.5
N5—C6—C7	106.72 (11)	H16B—C16—H16C	109.5
N5—Co1—N1—C2	82.07 (9)	N5—Co1—N8—C7	15.23 (9)
N8—Co1—N1—C2	81.1 (5)	N4—Co1—N8—C7	105.29 (9)
N4—Co1—N1—C2	−8.43 (8)	N9—Co1—N8—C7	−166.27 (9)
N9—Co1—N1—C2	−96.43 (8)	Cl1—Co1—N8—C7	−74.20 (9)
Cl1—Co1—N1—C2	171.58 (8)	N1—Co1—N9—C10	−142.93 (9)
Co1—N1—C2—C3	33.98 (12)	N5—Co1—N9—C10	75.2 (11)
N1—C2—C3—N4	−49.24 (13)	N8—Co1—N9—C10	37.28 (10)
C2—C3—N4—Co1	42.63 (11)	N4—Co1—N9—C10	132.35 (9)
N1—Co1—N4—C3	−19.47 (8)	Cl1—Co1—N9—C10	−53.79 (9)
N5—Co1—N4—C3	−109.82 (8)	Co1—N9—C10—C11	−81.78 (14)
N8—Co1—N4—C3	165.40 (8)	Co1—N9—C10—C15	101.80 (12)
N9—Co1—N4—C3	72.21 (8)	C15—C10—C11—C12	−1.4 (2)
Cl1—Co1—N4—C3	−19.4 (4)	N9—C10—C11—C12	−177.80 (13)
N1—Co1—N5—C6	−166.79 (9)	C10—C11—C12—C13	1.0 (2)
N8—Co1—N5—C6	13.13 (9)	C11—C12—C13—C14	0.5 (2)
N4—Co1—N5—C6	−82.01 (9)	C11—C12—C13—C16	179.51 (15)
N9—Co1—N5—C6	−24.9 (12)	C12—C13—C14—C15	−1.5 (2)
Cl1—Co1—N5—C6	104.13 (9)	C16—C13—C14—C15	179.43 (14)
Co1—N5—C6—C7	−37.90 (13)	C11—C10—C15—C14	0.34 (19)
N5—C6—C7—N8	50.01 (14)	N9—C10—C15—C14	176.77 (12)
C6—C7—N8—Co1	−39.65 (13)	C13—C14—C15—C10	1.1 (2)
N1—Co1—N8—C7	16.2 (6)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···Cl2i	0.873 (17)	2.465 (17)	3.2553 (11)	150.8 (14)
N4—H4B···Cl2ii	0.797 (17)	2.602 (18)	3.3299 (11)	152.5 (15)
O1—H1W···Cl3iii	0.79 (3)	2.34 (3)	3.1339 (14)	174 (2)
O1—H2W···Cl3iv	0.77 (3)	2.49 (3)	3.2470 (14)	170 (2)
N9—H9A···Cl3	0.87 (2)	2.45 (2)	3.3152 (11)	168.9 (17)
N8—H8B···Cl2	0.82 (2)	2.57 (2)	3.3046 (12)	150.8 (18)
N9—H9B···O1	0.841 (17)	2.090 (17)	2.9250 (16)	172.1 (15)
N1—H1A···Cl3	0.88 (2)	2.39 (2)	3.2467 (11)	163.5 (17)
N4—H4A···O1	0.801 (17)	2.461 (17)	3.0754 (17)	134.3 (14)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯Cl2i	0.873 (17)	2.465 (17)	3.2553 (11)	150.8 (14)
N4—H4B⋯Cl2ii	0.797 (17)	2.602 (18)	3.3299 (11)	152.5 (15)
O1—H1W⋯Cl3iii	0.79 (3)	2.34 (3)	3.1339 (14)	174 (2)
O1—H2W⋯Cl3iv	0.77 (3)	2.49 (3)	3.2470 (14)	170 (2)
N9—H9A⋯Cl3	0.87 (2)	2.45 (2)	3.3152 (11)	168.9 (17)
N8—H8B⋯Cl2	0.82 (2)	2.57 (2)	3.3046 (12)	150.8 (18)
N9—H9B⋯O1	0.841 (17)	2.090 (17)	2.9250 (16)	172.1 (15)
N1—H1A⋯Cl3	0.88 (2)	2.39 (2)	3.2467 (11)	163.5 (17)
N4—H4A⋯O1	0.801 (17)	2.461 (17)	3.0754 (17)	134.3 (14)

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