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

In the title salt, (C(8)H(15)N(3))[CdBr(4)], four Br atoms coordinate the Cd(II) atom in a distorted tetra-hedral geometry. In the crystal, weak N-H⋯Br inter-actions connect the anion to three symmetry-related cations. The crystal structure also displays very weak C-H⋯Br inter-actions.

Related literature

For background to 1,4-diaza­bicyclo­[2.2.2]octane derivatives and their properties, see: Basavaiah et al. (2003 ▶); Chen et al. (2010 ▶); Wang et al. (2005 ▶); Xiong et al. (2002 ▶); Ye et al. (2006 ▶).

Experimental

Crystal data

(C8H15N3)[CdBr4]

M = 585.27

Monoclinic,

a = 8.610 (3) Å

b = 14.071 (4) Å

c = 12.702 (4) Å

β = 94.136 (4)°

V = 1534.9 (8) Å3

Z = 4

Mo Kα radiation

μ = 11.82 mm−1

T = 293 K

0.2 × 0.2 × 0.2 mm

Data collection

Rigaku Mercury CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.470, T max = 1.000

16630 measured reflections

3518 independent reflections

2861 reflections with I > 2σ(I)

R int = 0.068

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.079

S = 0.76

3518 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.61 e Å−3

Δρmin = −0.88 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 datablocks I, global. DOI: 10.1107/S1600536810047495/bh2319sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810047495/bh2319Isup2.hkl

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

(C8H15N3)[CdBr4]	F(000) = 1088
Mr = 585.27	Dx = 2.533 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4263 reflections
a = 8.610 (3) Å	θ = 2.4–27.5°
b = 14.071 (4) Å	µ = 11.82 mm−1
c = 12.702 (4) Å	T = 293 K
β = 94.136 (4)°	Prism, colourless
V = 1534.9 (8) Å3	0.2 × 0.2 × 0.2 mm
Z = 4

Rigaku Mercury CCD diffractometer	3518 independent reflections
Radiation source: fine-focus sealed tube	2861 reflections with I > 2σ(I)
graphite	Rint = 0.068
Detector resolution: 28.5714 pixels mm-1	θmax = 27.5°, θmin = 3.1°
ω scans	h = −11→11
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −18→18
Tmin = 0.470, Tmax = 1.000	l = −16→16
16630 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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079	H-atom parameters constrained
S = 0.76	w = 1/[σ2(Fo2) + (0.0502P)2 + 0.2386P] where P = (Fo2 + 2Fc2)/3
3518 reflections	(Δ/σ)max = 0.018
145 parameters	Δρmax = 0.61 e Å−3
0 restraints	Δρmin = −0.88 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
Cd1	0.78773 (4)	0.22670 (2)	0.50861 (3)	0.02924 (11)
Br1	0.82000 (6)	0.40556 (3)	0.46315 (4)	0.03047 (13)
Br2	0.79028 (6)	0.24284 (3)	0.71414 (4)	0.03420 (13)
Br3	0.52068 (6)	0.15357 (3)	0.45098 (4)	0.03464 (13)
Br4	1.03019 (6)	0.13565 (3)	0.45657 (4)	0.03694 (14)
C8	0.4254 (6)	0.4480 (3)	0.6975 (4)	0.0314 (11)
N2	0.6179 (4)	0.5753 (2)	0.7314 (3)	0.0205 (7)
C5	0.9032 (5)	0.5513 (3)	0.7405 (4)	0.0328 (11)
H5A	0.9784	0.5564	0.8008	0.039*
H5B	0.9444	0.5081	0.6898	0.039*
N1	0.8754 (4)	0.6469 (2)	0.6913 (3)	0.0242 (8)
H1C	0.9610	0.6750	0.6691	0.029*
C6	0.7506 (6)	0.5138 (3)	0.7750 (4)	0.0378 (12)
H6A	0.7350	0.4490	0.7501	0.045*
H6B	0.7532	0.5132	0.8515	0.045*
C4	0.6267 (5)	0.5849 (3)	0.6140 (3)	0.0294 (10)
H4A	0.5365	0.6195	0.5842	0.035*
H4B	0.6263	0.5224	0.5819	0.035*
C3	0.7744 (5)	0.6376 (3)	0.5904 (3)	0.0283 (10)
H3A	0.8293	0.6027	0.5387	0.034*
H3B	0.7486	0.7000	0.5620	0.034*
C2	0.6364 (6)	0.6733 (3)	0.7808 (4)	0.0316 (11)
H2A	0.5586	0.7160	0.7484	0.038*
H2B	0.6215	0.6696	0.8557	0.038*
C7	0.4643 (5)	0.5354 (3)	0.7579 (3)	0.0279 (10)
H7A	0.4677	0.5215	0.8328	0.034*
H7B	0.3835	0.5825	0.7424	0.034*
N3	0.3933 (6)	0.3830 (3)	0.6497 (4)	0.0459 (12)
C1	0.7981 (5)	0.7107 (3)	0.7646 (4)	0.0300 (10)
H1A	0.7909	0.7744	0.7354	0.036*
H1B	0.8590	0.7135	0.8318	0.036*

	U11	U22	U33	U12	U13	U23
Cd1	0.02631 (19)	0.03071 (19)	0.0309 (2)	−0.00124 (14)	0.00314 (15)	0.00137 (14)
Br1	0.0324 (3)	0.0264 (2)	0.0335 (3)	0.00131 (19)	0.0088 (2)	−0.00169 (18)
Br2	0.0285 (3)	0.0477 (3)	0.0266 (3)	0.0031 (2)	0.0034 (2)	0.0044 (2)
Br3	0.0287 (3)	0.0421 (3)	0.0334 (3)	−0.0064 (2)	0.0042 (2)	−0.0070 (2)
Br4	0.0334 (3)	0.0351 (3)	0.0433 (3)	0.0054 (2)	0.0086 (2)	0.0016 (2)
C8	0.029 (3)	0.026 (2)	0.039 (3)	−0.008 (2)	0.003 (2)	0.010 (2)
N2	0.0180 (18)	0.0228 (18)	0.0213 (18)	0.0003 (14)	0.0053 (15)	0.0002 (14)
C5	0.023 (2)	0.032 (3)	0.043 (3)	0.007 (2)	0.003 (2)	0.002 (2)
N1	0.0148 (18)	0.031 (2)	0.029 (2)	−0.0028 (15)	0.0094 (15)	−0.0017 (15)
C6	0.027 (3)	0.034 (3)	0.052 (3)	0.008 (2)	−0.003 (2)	0.015 (2)
C4	0.027 (3)	0.045 (3)	0.016 (2)	−0.004 (2)	0.0037 (19)	−0.0024 (18)
C3	0.025 (2)	0.035 (3)	0.026 (2)	−0.002 (2)	0.007 (2)	0.0022 (18)
C2	0.033 (3)	0.031 (2)	0.033 (3)	−0.003 (2)	0.015 (2)	−0.013 (2)
C7	0.020 (2)	0.033 (2)	0.032 (3)	−0.0025 (19)	0.0067 (19)	0.0061 (19)
N3	0.051 (3)	0.032 (2)	0.053 (3)	−0.012 (2)	−0.004 (2)	0.011 (2)
C1	0.028 (2)	0.028 (2)	0.035 (3)	−0.003 (2)	0.008 (2)	−0.0084 (19)

Cd1—Br3	2.5766 (8)	N1—H1C	0.8997
Cd1—Br4	2.5760 (8)	C6—H6A	0.9700
Cd1—Br1	2.6015 (9)	C6—H6B	0.9700
Cd1—Br2	2.6191 (10)	C4—C3	1.521 (6)
C8—N3	1.122 (6)	C4—H4A	0.9700
C8—C7	1.475 (6)	C4—H4B	0.9700
N2—C7	1.497 (5)	C3—H3A	0.9700
N2—C6	1.506 (5)	C3—H3B	0.9700
N2—C4	1.505 (5)	C2—C1	1.516 (6)
N2—C2	1.519 (5)	C2—H2A	0.9700
C5—N1	1.495 (5)	C2—H2B	0.9700
C5—C6	1.510 (7)	C7—H7A	0.9700
C5—H5A	0.9700	C7—H7B	0.9700
C5—H5B	0.9700	C1—H1A	0.9700
N1—C1	1.485 (5)	C1—H1B	0.9700
N1—C3	1.501 (5)
Br3—Cd1—Br4	116.84 (3)	N2—C4—C3	110.0 (3)
Br3—Cd1—Br1	115.51 (2)	N2—C4—H4A	109.7
Br4—Cd1—Br1	108.83 (2)	C3—C4—H4A	109.7
Br3—Cd1—Br2	105.13 (2)	N2—C4—H4B	109.7
Br4—Cd1—Br2	110.50 (2)	C3—C4—H4B	109.7
Br1—Cd1—Br2	98.28 (2)	H4A—C4—H4B	108.2
N3—C8—C7	178.1 (5)	N1—C3—C4	108.4 (3)
C7—N2—C6	111.2 (3)	N1—C3—H3A	110.0
C7—N2—C4	111.4 (3)	C4—C3—H3A	110.0
C6—N2—C4	109.0 (3)	N1—C3—H3B	110.0
C7—N2—C2	108.3 (3)	C4—C3—H3B	110.0
C6—N2—C2	108.4 (4)	H3A—C3—H3B	108.4
C4—N2—C2	108.5 (3)	C1—C2—N2	109.2 (3)
N1—C5—C6	108.6 (4)	C1—C2—H2A	109.8
N1—C5—H5A	110.0	N2—C2—H2A	109.8
C6—C5—H5A	110.0	C1—C2—H2B	109.8
N1—C5—H5B	110.0	N2—C2—H2B	109.8
C6—C5—H5B	110.0	H2A—C2—H2B	108.3
H5A—C5—H5B	108.3	C8—C7—N2	111.5 (4)
C5—N1—C1	110.3 (3)	C8—C7—H7A	109.3
C5—N1—C3	110.1 (3)	N2—C7—H7A	109.3
C1—N1—C3	109.2 (3)	C8—C7—H7B	109.3
C5—N1—H1C	114.6	N2—C7—H7B	109.3
C1—N1—H1C	110.2	H7A—C7—H7B	108.0
C3—N1—H1C	102.0	N1—C1—C2	109.4 (3)
N2—C6—C5	110.1 (4)	N1—C1—H1A	109.8
N2—C6—H6A	109.6	C2—C1—H1A	109.8
C5—C6—H6A	109.6	N1—C1—H1B	109.8
N2—C6—H6B	109.6	C2—C1—H1B	109.8
C5—C6—H6B	109.6	H1A—C1—H1B	108.2
H6A—C6—H6B	108.1

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···Br1i	0.90	2.85	3.466 (4)	127
N1—H1C···Br2ii	0.90	2.69	3.325 (4)	128
N1—H1C···Br4i	0.90	3.11	3.711 (4)	126
C2—H2B···Br3iii	0.97	2.83	3.765 (5)	162
C4—H4B···Br1	0.97	2.85	3.643 (4)	140
C7—H7A···Br3iv	0.97	2.90	3.626 (4)	132
C7—H7B···Br2iii	0.97	2.78	3.683 (4)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1C⋯Br1i	0.90	2.85	3.466 (4)	127
N1—H1C⋯Br2ii	0.90	2.69	3.325 (4)	128
N1—H1C⋯Br4i	0.90	3.11	3.711 (4)	126
C2—H2B⋯Br3iii	0.97	2.83	3.765 (5)	162
C4—H4B⋯Br1	0.97	2.85	3.643 (4)	140
C7—H7A⋯Br3iv	0.97	2.90	3.626 (4)	132
C7—H7B⋯Br2iii	0.97	2.78	3.683 (4)	154

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