1-Cyano-methyl-1,4-diazo-niabicyclo-[2.2.2]octane tetra-chloridocadmate(II).

In the title salt, (C(8)H(15)N(3))[CdCl(4)], four Cl atoms coordinate the Cd(II) atom in a slightly distorted tetra-hedral geometry. In the crystal, each [CdCl(4)](2-) anion is connected to the 1-cyano-methyl-1,4-diazo-niabicyclo-[2.2.2]octane dications by N-H⋯Cl hydrogen bonds, forming chains parallel to [001]. C-H⋯Cl inter-actions also occur.

Related literature

For the use of 1,4-diaza­bicyclo­[2.2.2]octane (DABCO) and its derivatives, see: Basaviah et al. (2003 ▶); Zhang, Cheng et al. (2009 ▶). For ferroelectric properties of DABCO derivatives, see: Zhang, Ye et al. (2009 ▶, 2010 ▶). For related structures, see: Cai (2010 ▶); Wei (2010 ▶). For the isotypic cobaltate(II) analogue, see: Zhang & Zhu (2012 ▶).

Experimental

Crystal data

(C8H15N3)[CdCl4]

M = 407.43

Monoclinic,

a = 8.3747 (17) Å

b = 13.772 (3) Å

c = 12.153 (2) Å

β = 93.89 (3)°

V = 1398.4 (5) Å3

Z = 4

Mo Kα radiation

μ = 2.30 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 = 0.441, T max = 0.525

14246 measured reflections

3200 independent reflections

2899 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.059

S = 1.15

3200 reflections

150 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.46 e Å−3

Δρmin = −0.48 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: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812017801/pv2531sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812017801/pv2531Isup2.hkl

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

(C8H15N3)[CdCl4]	F(000) = 800
Mr = 407.43	Dx = 1.935 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2622 reflections
a = 8.3747 (17) Å	θ = 3.1–27.5°
b = 13.772 (3) Å	µ = 2.30 mm−1
c = 12.153 (2) Å	T = 298 K
β = 93.89 (3)°	Needle, colourless
V = 1398.4 (5) Å3	0.36 × 0.32 × 0.28 mm
Z = 4

Rigaku SCXmini diffractometer	3200 independent reflections
Radiation source: fine-focus sealed tube	2899 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.2°
ω scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −17→17
Tmin = 0.441, Tmax = 0.525	l = −15→15
14246 measured reflections

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)] = 0.026	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.059	w = 1/[σ2(Fo2) + (0.0208P)2 + 0.6019P] where P = (Fo2 + 2Fc2)/3
S = 1.15	(Δ/σ)max < 0.001
3200 reflections	Δρmax = 0.46 e Å−3
150 parameters	Δρmin = −0.48 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: 0.0332 (7)

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
Cd1	0.77481 (2)	0.228314 (13)	0.006713 (15)	0.02939 (9)
Cl2	0.78074 (8)	0.24012 (5)	0.21119 (5)	0.03509 (16)
Cl3	0.80985 (8)	0.40133 (4)	−0.03853 (5)	0.03183 (15)
Cl4	0.51643 (8)	0.15674 (5)	−0.05148 (5)	0.03630 (16)
Cl1	1.01183 (8)	0.13969 (5)	−0.04509 (6)	0.03678 (16)
N2	0.3731 (2)	0.42550 (13)	0.76461 (15)	0.0207 (4)
C4	0.1866 (3)	0.28852 (19)	0.7311 (2)	0.0314 (6)
H4A	0.1242	0.2852	0.6610	0.038*
H4B	0.1932	0.2238	0.7625	0.038*
N3	0.1084 (2)	0.35561 (15)	0.80727 (17)	0.0259 (4)
C2	0.2107 (3)	0.36440 (19)	0.9119 (2)	0.0286 (5)
H2A	0.2340	0.3005	0.9425	0.034*
H2B	0.1554	0.4016	0.9654	0.034*
C8	0.5761 (3)	0.55142 (19)	0.8006 (2)	0.0318 (6)
C3	0.3525 (3)	0.32615 (19)	0.7140 (2)	0.0350 (6)
H3A	0.4319	0.2822	0.7479	0.042*
H3B	0.3681	0.3295	0.6358	0.042*
C7	0.5335 (3)	0.46373 (17)	0.7366 (2)	0.0279 (5)
H7A	0.6144	0.4143	0.7522	0.033*
H7B	0.5307	0.4787	0.6585	0.033*
C1	0.3652 (3)	0.4152 (2)	0.88691 (19)	0.0305 (5)
H1A	0.3695	0.4788	0.9212	0.037*
H1B	0.4561	0.3778	0.9170	0.037*
N1	0.6122 (3)	0.61640 (17)	0.8522 (2)	0.0438 (6)
C6	0.0823 (3)	0.45326 (19)	0.7556 (2)	0.0359 (6)
H6A	0.0400	0.4978	0.8081	0.043*
H6B	0.0057	0.4484	0.6922	0.043*
C5	0.2410 (3)	0.4904 (2)	0.7198 (3)	0.0401 (7)
H5A	0.2391	0.4918	0.6399	0.048*
H5B	0.2592	0.5560	0.7469	0.048*
H1	0.024 (4)	0.333 (2)	0.817 (3)	0.050 (10)*

	U11	U22	U33	U12	U13	U23
Cd1	0.02778 (12)	0.02888 (12)	0.03141 (13)	−0.00082 (7)	0.00131 (8)	0.00145 (7)
Cl2	0.0308 (3)	0.0461 (4)	0.0282 (3)	0.0020 (3)	0.0009 (3)	0.0045 (3)
Cl3	0.0360 (3)	0.0254 (3)	0.0348 (3)	0.0025 (2)	0.0080 (3)	−0.0005 (2)
Cl4	0.0314 (3)	0.0443 (4)	0.0334 (3)	−0.0076 (3)	0.0032 (3)	−0.0087 (3)
Cl1	0.0341 (3)	0.0352 (3)	0.0414 (4)	0.0051 (3)	0.0048 (3)	−0.0012 (3)
N2	0.0200 (9)	0.0205 (9)	0.0216 (9)	0.0004 (7)	0.0024 (7)	−0.0003 (7)
C4	0.0300 (13)	0.0308 (13)	0.0338 (14)	−0.0037 (10)	0.0046 (11)	−0.0111 (10)
N3	0.0195 (10)	0.0303 (11)	0.0283 (11)	−0.0023 (8)	0.0044 (8)	−0.0023 (8)
C2	0.0292 (13)	0.0334 (13)	0.0234 (12)	−0.0054 (10)	0.0017 (10)	−0.0007 (10)
C8	0.0288 (13)	0.0309 (14)	0.0351 (14)	−0.0056 (10)	−0.0013 (11)	0.0092 (11)
C3	0.0356 (14)	0.0293 (13)	0.0415 (15)	−0.0075 (11)	0.0140 (12)	−0.0176 (11)
C7	0.0250 (12)	0.0286 (12)	0.0306 (13)	−0.0040 (10)	0.0063 (10)	0.0026 (10)
C1	0.0272 (13)	0.0440 (15)	0.0203 (12)	−0.0044 (11)	0.0024 (10)	−0.0012 (10)
N1	0.0557 (16)	0.0299 (12)	0.0442 (14)	−0.0120 (11)	−0.0080 (12)	0.0085 (11)
C6	0.0258 (13)	0.0368 (14)	0.0449 (16)	0.0084 (11)	0.0017 (11)	0.0057 (12)
C5	0.0296 (13)	0.0315 (14)	0.0578 (18)	0.0028 (11)	−0.0060 (12)	0.0187 (13)

Cd1—Cl4	2.4385 (8)	C2—H2A	0.9700
Cd1—Cl1	2.4486 (8)	C2—H2B	0.9700
Cd1—Cl3	2.4674 (8)	C8—N1	1.123 (3)
Cd1—Cl2	2.4874 (8)	C8—C7	1.467 (3)
N2—C5	1.496 (3)	C3—H3A	0.9700
N2—C1	1.499 (3)	C3—H3B	0.9700
N2—C7	1.503 (3)	C7—H7A	0.9700
N2—C3	1.505 (3)	C7—H7B	0.9700
C4—N3	1.491 (3)	C1—H1A	0.9700
C4—C3	1.511 (4)	C1—H1B	0.9700
C4—H4A	0.9700	C6—C5	1.515 (4)
C4—H4B	0.9700	C6—H6A	0.9700
N3—C2	1.489 (3)	C6—H6B	0.9700
N3—C6	1.494 (3)	C5—H5A	0.9700
N3—H1	0.79 (3)	C5—H5B	0.9700
C2—C1	1.520 (3)
Cl4—Cd1—Cl1	116.28 (3)	N2—C3—C4	109.66 (19)
Cl4—Cd1—Cl3	116.26 (3)	N2—C3—H3A	109.7
Cl1—Cd1—Cl3	108.26 (3)	C4—C3—H3A	109.7
Cl4—Cd1—Cl2	105.86 (3)	N2—C3—H3B	109.7
Cl1—Cd1—Cl2	109.14 (3)	C4—C3—H3B	109.7
Cl3—Cd1—Cl2	99.49 (2)	H3A—C3—H3B	108.2
C5—N2—C1	109.6 (2)	C8—C7—N2	110.9 (2)
C5—N2—C7	111.00 (18)	C8—C7—H7A	109.5
C1—N2—C7	110.95 (18)	N2—C7—H7A	109.5
C5—N2—C3	109.5 (2)	C8—C7—H7B	109.5
C1—N2—C3	107.91 (19)	N2—C7—H7B	109.5
C7—N2—C3	107.77 (18)	H7A—C7—H7B	108.0
N3—C4—C3	108.67 (19)	N2—C1—C2	109.70 (19)
N3—C4—H4A	110.0	N2—C1—H1A	109.7
C3—C4—H4A	110.0	C2—C1—H1A	109.7
N3—C4—H4B	110.0	N2—C1—H1B	109.7
C3—C4—H4B	110.0	C2—C1—H1B	109.7
H4A—C4—H4B	108.3	H1A—C1—H1B	108.2
C2—N3—C4	109.2 (2)	N3—C6—C5	108.6 (2)
C2—N3—C6	110.2 (2)	N3—C6—H6A	110.0
C4—N3—C6	110.8 (2)	C5—C6—H6A	110.0
C2—N3—H1	112 (2)	N3—C6—H6B	110.0
C4—N3—H1	107 (2)	C5—C6—H6B	110.0
C6—N3—H1	108 (2)	H6A—C6—H6B	108.4
N3—C2—C1	108.38 (19)	N2—C5—C6	109.6 (2)
N3—C2—H2A	110.0	N2—C5—H5A	109.8
C1—C2—H2A	110.0	C6—C5—H5A	109.8
N3—C2—H2B	110.0	N2—C5—H5B	109.8
C1—C2—H2B	110.0	C6—C5—H5B	109.8
H2A—C2—H2B	108.4	H5A—C5—H5B	108.2
N1—C8—C7	177.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1···Cl2i	0.79 (3)	2.54 (3)	3.193 (2)	141 (3)
N3—H1···Cl3ii	0.79 (3)	2.76 (3)	3.285 (2)	126 (3)
C1—H1A···Cl3iii	0.97	2.70	3.507 (3)	141 (2)
C3—H3B···Cl4iv	0.97	2.67	3.599 (3)	160 (2)
C4—H4A···Cl1i	0.97	2.81	3.704 (3)	153 (2)
C7—H7A···Cl2iv	0.97	2.61	3.514 (3)	155 (2)
C7—H7B···Cl4v	0.97	2.79	3.489 (3)	129 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1⋯Cl2i	0.79 (3)	2.54 (3)	3.193 (2)	141 (3)
N3—H1⋯Cl3ii	0.79 (3)	2.76 (3)	3.285 (2)	126 (3)
C1—H1A⋯Cl3iii	0.97	2.70	3.507 (3)	141 (2)
C3—H3B⋯Cl4iv	0.97	2.67	3.599 (3)	160 (2)
C4—H4A⋯Cl1i	0.97	2.81	3.704 (3)	153 (2)
C7—H7A⋯Cl2iv	0.97	2.61	3.514 (3)	155 (2)
C7—H7B⋯Cl4v	0.97	2.79	3.489 (3)	129 (2)

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