1-(4-Hy-droxy-phen-yl)piperazine-1,4-diium tetra-chlorido-cobalt(II) monohydrate.

The asymmetric unit of the title inorganic-organic hybrid compound, (C10H16N2O)[CoCl4]·H2O, consists of a tetrahedral [CoCl4](2-) anion, together with a [C10H18N2O](2+) cation and a water mol-ecule. Crystal cohesion is achieved through N-H⋯Cl, O-H⋯Cl and N-H⋯O hydrogen bonds between organic cations, inorganic anions and the water mol-ecules, building up a three-dimensional network.

Related literature

For spectroscopic and electrochemical properties of hybrid compounds, see: Bu et al. (2001 ▶). For a similar structural arrangement, see: Aza­dbakht et al. (2012 ▶). For the coordination of cobalt, see: Reiss (2013 ▶); Oh et al. (2011 ▶).

Experimental

Crystal data

(C10H16N2O)[CoCl4]·H2O

M = 398.99

Triclinic,

a = 7.455 (1) Å

b = 8.002 (2) Å

c = 14.105 (1) Å

α = 91.72 (1)°

β = 96.98 (1)°

γ = 99.19 (1)°

V = 823.4 (2) Å3

Z = 2

Mo Kα radiation

μ = 1.69 mm−1

T = 298 K

0.6 × 0.3 × 0.2 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.607, T max = 0.712

4220 measured reflections

3586 independent reflections

3110 reflections with I > 2σ(I)

R int = 0.027

2 standard reflections every 120 min intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.102

S = 1.08

3586 reflections

245 parameters

All H-atom parameters refined

Δρmax = 0.73 e Å−3

Δρmin = −0.45 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814001767/cq2009sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814001767/cq2009Isup2.hkl

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

(C10H16N2O)[CoCl4]·H2O	Z = 2
Mr = 398.99	F(000) = 406
Triclinic, P1	Dx = 1.609 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.455 (1) Å	Cell parameters from 25 reflections
b = 8.002 (2) Å	θ = 10–15°
c = 14.105 (1) Å	µ = 1.69 mm−1
α = 91.72 (1)°	T = 298 K
β = 96.98 (1)°	Prism, blue
γ = 99.19 (1)°	0.6 × 0.3 × 0.2 mm
V = 823.4 (2) Å3

Enraf–Nonius CAD-4 diffractometer	3110 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.027
Graphite monochromator	θmax = 27.0°, θmin = 2.6°
non–profiled ω/2θ scans	h = −9→1
Absorption correction: ψ scan (North et al., 1968)	k = −10→10
Tmin = 0.607, Tmax = 0.712	l = −17→17
4220 measured reflections	2 standard reflections every 120 min
3586 independent reflections	intensity decay: 1%

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)] = 0.037	All H-atom parameters refined
wR(F2) = 0.102	w = 1/[σ2(Fo2) + (0.0592P)2 + 0.2936P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.001
3586 reflections	Δρmax = 0.73 e Å−3
245 parameters	Δρmin = −0.45 e Å−3
0 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: 0.019 (2)

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
Co	0.13891 (4)	0.68672 (4)	0.31676 (2)	0.03430 (13)
Cl1	−0.02197 (8)	0.72320 (8)	0.44103 (4)	0.04349 (16)
Cl2	0.43614 (7)	0.72221 (8)	0.37771 (4)	0.04201 (16)
Cl3	0.09100 (10)	0.89884 (9)	0.21635 (5)	0.05405 (19)
Cl4	0.04924 (9)	0.43236 (8)	0.23402 (5)	0.0534 (2)
N1	0.6315 (3)	0.2602 (2)	0.20897 (12)	0.0300 (4)
N2	0.6528 (3)	0.1678 (3)	0.40592 (14)	0.0362 (4)
O	0.3173 (3)	0.2976 (3)	−0.16914 (12)	0.0487 (4)
OW	0.2791 (3)	0.1012 (3)	0.42756 (18)	0.0602 (6)
C1	0.3886 (3)	0.2802 (3)	−0.07645 (16)	0.0375 (5)
C2	0.2788 (4)	0.2306 (4)	−0.00674 (18)	0.0475 (6)
C3	0.3570 (3)	0.2225 (4)	0.08687 (17)	0.0447 (6)
C4	0.5440 (3)	0.2645 (3)	0.10896 (15)	0.0319 (4)
C5	0.6549 (3)	0.3101 (3)	0.03969 (17)	0.0395 (5)
C6	0.5760 (4)	0.3167 (3)	−0.05438 (17)	0.0422 (5)
C7	0.6411 (4)	0.3453 (3)	0.37993 (17)	0.0416 (5)
C8	0.5389 (4)	0.3477 (3)	0.28063 (17)	0.0402 (5)
C9	0.6456 (4)	0.0825 (3)	0.23609 (17)	0.0363 (5)
C10	0.7445 (3)	0.0816 (3)	0.33578 (17)	0.0379 (5)
HWA	0.193 (6)	0.050 (5)	0.384 (3)	0.082 (12)*
HWB	0.227 (6)	0.161 (5)	0.454 (3)	0.080 (13)*
H1	0.213 (5)	0.259 (5)	−0.172 (3)	0.066 (11)*
H2	0.144 (4)	0.201 (4)	−0.019 (2)	0.055 (8)*
H3	0.284 (4)	0.180 (4)	0.134 (2)	0.054 (8)*
H5	0.781 (4)	0.344 (4)	0.056 (2)	0.052 (8)*
H6	0.646 (4)	0.344 (4)	−0.102 (2)	0.052 (8)*
H7A	0.578 (5)	0.390 (4)	0.426 (2)	0.064 (9)*
H7B	0.769 (5)	0.410 (4)	0.385 (2)	0.054 (8)*
H8A	0.415 (4)	0.288 (4)	0.278 (2)	0.052 (8)*
H8B	0.531 (4)	0.449 (4)	0.264 (2)	0.051 (8)*
H9A	0.528 (5)	0.019 (4)	0.231 (2)	0.054 (8)*
H9B	0.718 (4)	0.045 (4)	0.191 (2)	0.045 (7)*
H10A	0.749 (4)	−0.027 (4)	0.353 (2)	0.047 (7)*
H10B	0.865 (4)	0.147 (4)	0.340 (2)	0.045 (7)*
H1N	0.752 (4)	0.317 (4)	0.209 (2)	0.046 (7)*
H2NA	0.551 (5)	0.113 (4)	0.411 (2)	0.063 (10)*
H2NB	0.722 (4)	0.175 (4)	0.464 (2)	0.046 (8)*

	U11	U22	U33	U12	U13	U23
Co	0.03205 (18)	0.03383 (18)	0.03517 (19)	0.00247 (12)	0.00115 (12)	0.00040 (12)
Cl1	0.0365 (3)	0.0511 (3)	0.0436 (3)	0.0088 (2)	0.0072 (2)	−0.0033 (2)
Cl2	0.0314 (3)	0.0489 (3)	0.0448 (3)	0.0073 (2)	0.0020 (2)	−0.0056 (2)
Cl3	0.0535 (4)	0.0515 (4)	0.0533 (4)	0.0005 (3)	−0.0020 (3)	0.0208 (3)
Cl4	0.0400 (3)	0.0473 (3)	0.0682 (4)	−0.0050 (3)	0.0099 (3)	−0.0209 (3)
N1	0.0349 (9)	0.0261 (8)	0.0281 (8)	0.0025 (7)	0.0030 (7)	0.0021 (6)
N2	0.0353 (10)	0.0397 (10)	0.0316 (9)	0.0020 (8)	0.0003 (8)	0.0082 (8)
O	0.0569 (12)	0.0537 (11)	0.0325 (9)	0.0054 (9)	−0.0026 (8)	0.0072 (7)
OW	0.0417 (10)	0.0598 (13)	0.0764 (15)	0.0048 (9)	0.0080 (10)	−0.0254 (11)
C1	0.0479 (13)	0.0318 (10)	0.0322 (11)	0.0078 (9)	0.0015 (9)	0.0000 (8)
C2	0.0400 (13)	0.0566 (15)	0.0408 (13)	−0.0031 (11)	−0.0019 (10)	0.0074 (11)
C3	0.0384 (12)	0.0569 (15)	0.0347 (12)	−0.0052 (11)	0.0037 (10)	0.0090 (10)
C4	0.0378 (11)	0.0266 (9)	0.0301 (10)	0.0036 (8)	0.0014 (8)	0.0009 (7)
C5	0.0371 (12)	0.0469 (13)	0.0350 (11)	0.0074 (10)	0.0053 (9)	0.0024 (9)
C6	0.0466 (13)	0.0491 (13)	0.0322 (11)	0.0070 (11)	0.0107 (10)	0.0042 (10)
C7	0.0589 (15)	0.0334 (11)	0.0323 (11)	0.0088 (11)	0.0046 (10)	−0.0006 (9)
C8	0.0569 (15)	0.0344 (11)	0.0340 (11)	0.0193 (11)	0.0079 (10)	0.0032 (9)
C9	0.0458 (13)	0.0257 (10)	0.0375 (12)	0.0092 (9)	0.0013 (10)	0.0017 (8)
C10	0.0395 (12)	0.0332 (11)	0.0413 (12)	0.0096 (10)	−0.0003 (9)	0.0071 (9)

Co—Cl2	2.2475 (7)	C2—C3	1.385 (3)
Co—Cl4	2.2772 (7)	C2—H2	0.99 (3)
Co—Cl1	2.2777 (7)	C3—C4	1.376 (3)
Co—Cl3	2.2868 (7)	C3—H3	0.95 (3)
N1—C4	1.484 (3)	C4—C5	1.376 (3)
N1—C9	1.500 (3)	C5—C6	1.391 (3)
N1—C8	1.506 (3)	C5—H5	0.94 (3)
N1—H1N	0.94 (3)	C6—H6	0.91 (3)
N2—C10	1.482 (3)	C7—C8	1.513 (3)
N2—C7	1.491 (3)	C7—H7A	0.94 (3)
N2—H2NA	0.83 (4)	C7—H7B	1.00 (3)
N2—H2NB	0.91 (3)	C8—H8A	0.96 (3)
O—C1	1.370 (3)	C8—H8B	0.86 (3)
O—H1	0.79 (4)	C9—C10	1.507 (3)
OW—HWA	0.87 (4)	C9—H9A	0.93 (3)
OW—HWB	0.77 (4)	C9—H9B	0.95 (3)
C1—C6	1.376 (4)	C10—H10A	0.92 (3)
C1—C2	1.382 (4)	C10—H10B	0.96 (3)
Cl2—Co—Cl4	111.38 (3)	C3—C4—N1	120.36 (19)
Cl2—Co—Cl1	106.87 (3)	C4—C5—C6	119.3 (2)
Cl4—Co—Cl1	113.97 (3)	C4—C5—H5	120.3 (19)
Cl2—Co—Cl3	109.60 (3)	C6—C5—H5	120.3 (19)
Cl4—Co—Cl3	108.94 (3)	C1—C6—C5	119.6 (2)
Cl1—Co—Cl3	105.87 (3)	C1—C6—H6	119.3 (19)
C4—N1—C9	111.55 (16)	C5—C6—H6	121.1 (19)
C4—N1—C8	113.32 (17)	N2—C7—C8	110.53 (19)
C9—N1—C8	110.62 (17)	N2—C7—H7A	106 (2)
C4—N1—H1N	105.0 (18)	C8—C7—H7A	111 (2)
C9—N1—H1N	106.4 (18)	N2—C7—H7B	108.3 (18)
C8—N1—H1N	109.6 (17)	C8—C7—H7B	111.9 (18)
C10—N2—C7	110.87 (18)	H7A—C7—H7B	109 (3)
C10—N2—H2NA	111 (2)	N1—C8—C7	110.1 (2)
C7—N2—H2NA	112 (2)	N1—C8—H8A	107.9 (19)
C10—N2—H2NB	109.1 (18)	C7—C8—H8A	110.1 (19)
C7—N2—H2NB	106.2 (18)	N1—C8—H8B	109 (2)
H2NA—N2—H2NB	108 (3)	C7—C8—H8B	112 (2)
C1—O—H1	105 (3)	H8A—C8—H8B	107 (3)
HWA—OW—HWB	102 (4)	N1—C9—C10	110.75 (18)
O—C1—C6	117.2 (2)	N1—C9—H9A	108.8 (19)
O—C1—C2	122.2 (2)	C10—C9—H9A	111.0 (19)
C6—C1—C2	120.6 (2)	N1—C9—H9B	103.1 (17)
C1—C2—C3	119.9 (2)	C10—C9—H9B	109.7 (17)
C1—C2—H2	123.5 (18)	H9A—C9—H9B	113 (2)
C3—C2—H2	116.6 (18)	N2—C10—C9	110.96 (19)
C4—C3—C2	119.1 (2)	N2—C10—H10A	108.8 (18)
C4—C3—H3	120.2 (18)	C9—C10—H10A	110.8 (18)
C2—C3—H3	120.5 (18)	N2—C10—H10B	104.4 (17)
C5—C4—C3	121.4 (2)	C9—C10—H10B	110.3 (17)
C5—C4—N1	118.25 (19)	H10A—C10—H10B	111 (2)

D—H···A	D—H	H···A	D···A	D—H···A
OW—HWA···Cl3i	0.87 (4)	2.59 (4)	3.381 (3)	150 (4)
OW—HWB···Cl1ii	0.78 (4)	2.51 (4)	3.264 (3)	164 (4)
O—H1···Cl3iii	0.79 (4)	2.41 (4)	3.177 (3)	165 (4)
N1—H1N···Cl4iv	0.94 (3)	2.24 (3)	3.171 (2)	170 (2)
N2—H2NA···OW	0.83 (4)	2.06 (4)	2.807 (2)	151 (3)
N2—H2NB···Cl1v	0.91 (3)	2.47 (3)	3.267 (2)	147 (2)
N2—H2NB···Cl2v	0.91 (3)	2.81 (3)	3.324 (2)	117 (2)

Table 1

Selected bond lengths (Å)

Co—Cl2	2.2475 (7)
Co—Cl4	2.2772 (7)
Co—Cl1	2.2777 (7)
Co—Cl3	2.2868 (7)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
OW—HWA⋯Cl3i	0.87 (4)	2.59 (4)	3.381 (3)	150 (4)
OW—HWB⋯Cl1ii	0.78 (4)	2.51 (4)	3.264 (3)	164 (4)
O—H1⋯Cl3iii	0.79 (4)	2.41 (4)	3.177 (3)	165 (4)
N1—H1N⋯Cl4iv	0.94 (3)	2.24 (3)	3.171 (2)	170 (2)
N2—H2NA⋯OW	0.83 (4)	2.06 (4)	2.807 (2)	151 (3)
N2—H2NB⋯Cl1v	0.91 (3)	2.47 (3)	3.267 (2)	147 (2)
N2—H2NB⋯Cl2v	0.91 (3)	2.81 (3)	3.324 (2)	117 (2)

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