Aqua-trichlorido(1-cyano-methyl-4-aza-1-azoniabicyclo-[2.2.2]octane-κN(4))copper(II) monohydrate.

The asymmetric unit of the title compound, [CuCl(3)(C(8)H(14)N(3))(H(2)O)]·H(2)O, comprises a neutral complex and a mol-ecule of free water. The complex contains coordinated Cu(II) ions, with Cu-Cl distances ranging from 2.3471 (8) to 2.4011 (8) Å, and with Cu-N and Cu-O distances of 2.0775 (19) and 2.0048 (18) Å, respectively. The resulting coordination polyhedron is a trigonal bipyramid with the Cl atoms in the equatorial plane. In the crystal, O-H⋯Cl and O-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional structure.

Related literature

For background to dielectric-ferroelectric materials, see: Fu et al. (2010 ▶); Zhang et al. (2008 ▶). The title compound was prepared in an attempt to make analogs of (dabcoH2)2Cl3[CuCl3(H2O)2]·H2O (Wei & Willett, 1996 ▶) and (dabcoH2)CuCl4 and Zn(dabcoH)Cl3 (Wei & Willett, 2001 ▶) (dabco is 1,4-diazabicyclo[2.2.2]octan).

Experimental

Crystal data

[CuCl3(C8H14N3)(H2O)]·H2O

M = 358.14

Monoclinic,

a = 24.301 (5) Å

b = 8.2794 (17) Å

c = 14.069 (3) Å

β = 101.69 (3)°

V = 2771.9 (10) Å3

Z = 8

Mo Kα radiation

μ = 2.15 mm−1

T = 298 K

0.36 × 0.32 × 0.28 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.963, T max = 0.971

13618 measured reflections

3155 independent reflections

2881 reflections with I > 2σ(I)

R int = 0.068

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.093

S = 1.10

3155 reflections

170 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.62 e Å−3

Δρmin = −0.86 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812017205/fj2535sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812017205/fj2535Isup2.hkl

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

[CuCl3(C8H14N3)(H2O)]·H2O	F(000) = 1464
Mr = 358.14	Dx = 1.716 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 12903 reflections
a = 24.301 (5) Å	θ = 3.1–27.5°
b = 8.2794 (17) Å	µ = 2.15 mm−1
c = 14.069 (3) Å	T = 298 K
β = 101.69 (3)°	Block, green
V = 2771.9 (10) Å3	0.36 × 0.32 × 0.28 mm
Z = 8

Rigaku SCXmini diffractometer	3155 independent reflections
Radiation source: fine-focus sealed tube	2881 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.068
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.1°
ω scans	h = −31→31
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −10→10
Tmin = 0.963, Tmax = 0.971	l = −18→18
13618 measured reflections

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ2(Fo2) + (0.037P)2 + 2.7164P] where P = (Fo2 + 2Fc2)/3
3155 reflections	(Δ/σ)max < 0.001
170 parameters	Δρmax = 0.62 e Å−3
0 restraints	Δρmin = −0.86 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
C1	0.08955 (10)	0.0927 (3)	0.17062 (17)	0.0250 (5)
H1A	0.0550	0.0937	0.1951	0.030*
H1B	0.1083	−0.0094	0.1887	0.030*
C2	0.07568 (10)	0.1079 (3)	0.05965 (17)	0.0246 (5)
H2A	0.0922	0.0182	0.0309	0.030*
H2B	0.0353	0.1042	0.0366	0.030*
C3	0.09449 (10)	0.3817 (3)	0.19080 (16)	0.0215 (5)
H3A	0.1182	0.4723	0.2164	0.026*
H3B	0.0621	0.3820	0.2212	0.026*
C4	0.07485 (10)	0.4018 (3)	0.08053 (16)	0.0232 (5)
H4A	0.0341	0.4002	0.0636	0.028*
H4B	0.0877	0.5047	0.0603	0.028*
C5	0.17741 (9)	0.2318 (3)	0.17037 (17)	0.0215 (5)
H5A	0.1965	0.1285	0.1806	0.026*
H5B	0.2031	0.3142	0.2019	0.026*
C6	0.16180 (10)	0.2671 (3)	0.06133 (18)	0.0261 (5)
H6A	0.1764	0.3718	0.0479	0.031*
H6B	0.1782	0.1859	0.0258	0.031*
C7	0.08423 (11)	0.2867 (3)	−0.07951 (18)	0.0300 (6)
H7A	0.0986	0.3898	−0.0964	0.036*
H7B	0.1023	0.2023	−0.1099	0.036*
C8	0.02328 (12)	0.2805 (3)	−0.11707 (18)	0.0314 (6)
Cl2	0.20113 (3)	0.44899 (7)	0.38684 (4)	0.02851 (16)
Cl3	0.19677 (3)	−0.05276 (7)	0.34199 (4)	0.02920 (16)
Cl4	0.06069 (3)	0.23400 (10)	0.39370 (5)	0.03668 (18)
Cu1	0.151563 (11)	0.19653 (3)	0.364527 (19)	0.01994 (11)
H10	0.217 (2)	0.384 (6)	0.666 (3)	0.091 (19)*
H11	0.187 (2)	0.295 (5)	0.709 (3)	0.074 (17)*
H12	0.1751 (17)	0.215 (5)	0.543 (3)	0.063 (13)*
H13	0.2148 (17)	0.111 (4)	0.521 (3)	0.055 (10)*
N1	0.12648 (8)	0.2280 (2)	0.21552 (13)	0.0166 (4)
N2	0.09851 (8)	0.2654 (2)	0.02936 (14)	0.0197 (4)
N3	−0.02358 (12)	0.2753 (4)	−0.14739 (19)	0.0471 (7)
O1	0.18732 (11)	0.3383 (3)	0.66114 (18)	0.0418 (5)
O2	0.17734 (8)	0.1430 (2)	0.50550 (13)	0.0276 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0211 (12)	0.0239 (12)	0.0279 (12)	−0.0077 (10)	0.0001 (9)	0.0016 (9)
C2	0.0241 (12)	0.0221 (12)	0.0263 (12)	−0.0055 (10)	0.0018 (9)	−0.0047 (9)
C3	0.0207 (11)	0.0226 (12)	0.0208 (11)	0.0067 (9)	0.0030 (9)	0.0008 (8)
C4	0.0241 (12)	0.0215 (12)	0.0228 (12)	0.0048 (9)	0.0019 (9)	−0.0007 (9)
C5	0.0121 (11)	0.0287 (12)	0.0238 (12)	0.0007 (9)	0.0036 (9)	0.0016 (9)
C6	0.0133 (12)	0.0402 (14)	0.0255 (13)	−0.0021 (10)	0.0057 (9)	0.0013 (10)
C7	0.0272 (14)	0.0432 (16)	0.0190 (12)	0.0016 (11)	0.0035 (10)	−0.0018 (10)
C8	0.0329 (16)	0.0393 (15)	0.0204 (12)	0.0038 (12)	0.0013 (11)	−0.0021 (10)
Cl2	0.0248 (3)	0.0267 (3)	0.0309 (3)	−0.0035 (2)	−0.0016 (2)	−0.0039 (2)
Cl3	0.0303 (3)	0.0266 (3)	0.0309 (3)	0.0101 (2)	0.0067 (2)	0.0034 (2)
Cl4	0.0170 (3)	0.0620 (5)	0.0328 (4)	0.0085 (3)	0.0093 (3)	0.0129 (3)
Cu1	0.01484 (17)	0.02434 (18)	0.01982 (17)	0.00123 (10)	0.00157 (11)	0.00118 (10)
N1	0.0110 (9)	0.0189 (9)	0.0196 (9)	−0.0008 (7)	0.0023 (7)	0.0001 (7)
N2	0.0159 (10)	0.0259 (10)	0.0172 (9)	0.0007 (8)	0.0029 (7)	−0.0018 (7)
N3	0.0357 (16)	0.0609 (18)	0.0387 (15)	0.0060 (13)	−0.0065 (11)	−0.0060 (12)
O1	0.0392 (14)	0.0456 (13)	0.0378 (13)	0.0086 (11)	0.0013 (10)	−0.0065 (10)
O2	0.0252 (10)	0.0324 (10)	0.0229 (9)	0.0049 (8)	−0.0007 (7)	0.0000 (7)

C1—N1	1.493 (3)	C6—N2	1.513 (3)
C1—C2	1.534 (3)	C6—H6A	0.9700
C1—H1A	0.9700	C6—H6B	0.9700
C1—H1B	0.9700	C7—C8	1.469 (4)
C2—N2	1.512 (3)	C7—N2	1.511 (3)
C2—H2A	0.9700	C7—H7A	0.9700
C2—H2B	0.9700	C7—H7B	0.9700
C3—N1	1.495 (3)	C8—N3	1.133 (4)
C3—C4	1.537 (3)	Cl2—Cu1	2.4011 (8)
C3—H3A	0.9700	Cl3—Cu1	2.3893 (7)
C3—H3B	0.9700	Cl4—Cu1	2.3471 (8)
C4—N2	1.514 (3)	Cu1—O2	2.0048 (18)
C4—H4A	0.9700	Cu1—N1	2.0775 (19)
C4—H4B	0.9700	O1—H10	0.80 (5)
C5—N1	1.502 (3)	O1—H11	0.77 (5)
C5—C6	1.532 (3)	O2—H12	0.80 (4)
C5—H5A	0.9700	O2—H13	0.93 (4)
C5—H5B	0.9700
N1—C1—C2	111.02 (18)	H6A—C6—H6B	108.3
N1—C1—H1A	109.4	C8—C7—N2	111.6 (2)
C2—C1—H1A	109.4	C8—C7—H7A	109.3
N1—C1—H1B	109.4	N2—C7—H7A	109.3
C2—C1—H1B	109.4	C8—C7—H7B	109.3
H1A—C1—H1B	108.0	N2—C7—H7B	109.3
N2—C2—C1	109.86 (18)	H7A—C7—H7B	108.0
N2—C2—H2A	109.7	N3—C8—C7	179.0 (3)
C1—C2—H2A	109.7	O2—Cu1—N1	174.24 (8)
N2—C2—H2B	109.7	O2—Cu1—Cl4	88.43 (6)
C1—C2—H2B	109.7	N1—Cu1—Cl4	93.78 (6)
H2A—C2—H2B	108.2	O2—Cu1—Cl3	83.13 (6)
N1—C3—C4	111.57 (18)	N1—Cu1—Cl3	91.32 (5)
N1—C3—H3A	109.3	Cl4—Cu1—Cl3	127.71 (3)
C4—C3—H3A	109.3	O2—Cu1—Cl2	90.87 (6)
N1—C3—H3B	109.3	N1—Cu1—Cl2	93.43 (6)
C4—C3—H3B	109.3	Cl4—Cu1—Cl2	109.08 (3)
H3A—C3—H3B	108.0	Cl3—Cu1—Cl2	122.51 (3)
N2—C4—C3	109.19 (18)	C1—N1—C3	107.48 (17)
N2—C4—H4A	109.8	C1—N1—C5	108.24 (18)
C3—C4—H4A	109.8	C3—N1—C5	108.54 (18)
N2—C4—H4B	109.8	C1—N1—Cu1	111.19 (14)
C3—C4—H4B	109.8	C3—N1—Cu1	111.95 (13)
H4A—C4—H4B	108.3	C5—N1—Cu1	109.34 (14)
N1—C5—C6	111.69 (18)	C7—N2—C2	111.36 (18)
N1—C5—H5A	109.3	C7—N2—C6	108.14 (18)
C6—C5—H5A	109.3	C2—N2—C6	109.45 (19)
N1—C5—H5B	109.3	C7—N2—C4	111.33 (18)
C6—C5—H5B	109.3	C2—N2—C4	108.25 (18)
H5A—C5—H5B	107.9	C6—N2—C4	108.26 (18)
N2—C6—C5	109.06 (18)	H10—O1—H11	109 (5)
N2—C6—H6A	109.9	Cu1—O2—H12	116 (3)
C5—C6—H6A	109.9	Cu1—O2—H13	113 (2)
N2—C6—H6B	109.9	H12—O2—H13	104 (4)
C5—C6—H6B	109.9

D—H···A	D—H	H···A	D···A	D—H···A
O2—H13···Cl2i	0.93 (4)	2.24 (4)	3.128 (2)	159 (3)
O2—H12···O1	0.80 (4)	1.92 (4)	2.693 (3)	160 (4)
O1—H11···Cl3ii	0.77 (5)	2.72 (5)	3.447 (3)	159 (4)
O1—H10···Cl3i	0.80 (5)	2.54 (6)	3.337 (3)	171 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H13⋯Cl2i	0.93 (4)	2.24 (4)	3.128 (2)	159 (3)
O2—H12⋯O1	0.80 (4)	1.92 (4)	2.693 (3)	160 (4)
O1—H11⋯Cl3ii	0.77 (5)	2.72 (5)	3.447 (3)	159 (4)
O1—H10⋯Cl3i	0.80 (5)	2.54 (6)	3.337 (3)	171 (5)

Symmetry codes: (i) ; (ii) .