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

In the title salt, (C(8)H(15)N(3))[CoCl(4)], the four chloride anions coordinate the Co(II) ion in a distorted tetra-hedral geometry. In the crystal, N-H⋯Cl hydrogen bonds link cations and anions into chains running along the c axis. The crystal packing is further stabilized by weak C-H⋯Cl and C-H⋯N inter-actions.

Related literature

Crystal structures of related Cu and n class="Chemical">Cd analogs were reported by Wei (2010 ▶) and Zhang & Zhu (2012 ▶), respectively. For ferroelectric properties of 1,4-diaza­bicyclo­[2.2.2]octane deriv­atives, see: Zhang et al. (2009 ▶, 2010 ▶).

Experimental

Crystal data

(C8H15N3)[n class="Chemical">CoCl4]

M = 353.96

Monoclinic,

a = 8.3085 (17) Å

b = 13.604 (3) Å

c = 12.185 (2) Å

β = 93.78 (3)°

V = 1374.3 (5) Å3

Z = 4

Mo Kα radiation

μ = 2.00 mm−1

T = 298 K

0.36 × 0.32 × 0.28 mm

Data collection

Rigaku Mercury70 Cn class="Chemical">CD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.491, T max = 0.571

13757 measured reflections

3152 independent reflections

2724 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.135

S = 0.98

3152 reflections

149 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.58 e Å−3

Δρmin = −0.52 e Å−3

Data collection: SCXmini Benchtop Crystallography System Software (Rigaku, 2006 ▶); cell refinement: SCXmini Benchtop Crystallography System Software; data reduction: SCXmini Benchtop Crystallography System Software; 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/S1600536812017187/cv5283sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812017187/cv5283Isup2.hkl

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

(C8H15N3)[CoCl4]	F(000) = 716
Mr = 353.96	Dx = 1.711 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2622 reflections
a = 8.3085 (17) Å	θ = 3.1–27.5°
b = 13.604 (3) Å	µ = 2.00 mm−1
c = 12.185 (2) Å	T = 298 K
β = 93.78 (3)°	Block, blue
V = 1374.3 (5) Å3	0.36 × 0.32 × 0.28 mm
Z = 4

Rigaku Mercury70 CCD diffractometer	3152 independent reflections
Radiation source: fine-focus sealed tube	2724 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.0°
ω scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −17→17
Tmin = 0.491, Tmax = 0.571	l = −15→15
13757 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 0.98	w = 1/[σ2(Fo2) + (0.069P)2 + 4.1266P] where P = (Fo2 + 2Fc2)/3
3152 reflections	(Δ/σ)max = 0.001
149 parameters	Δρmax = 0.58 e Å−3
0 restraints	Δρmin = −0.52 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
Co1	0.22754 (6)	1.23132 (4)	−0.01115 (4)	0.02235 (17)
Cl2	0.22305 (12)	1.24111 (8)	−0.19820 (7)	0.0304 (2)
Cl3	0.19972 (12)	1.39179 (7)	0.04142 (8)	0.0276 (2)
Cl4	0.00899 (12)	1.14672 (8)	0.04230 (8)	0.0321 (2)
Cl1	0.46675 (12)	1.16243 (8)	0.04912 (8)	0.0325 (2)
N2	0.1021 (4)	0.8570 (2)	0.3083 (3)	0.0232 (7)
C8	0.5802 (5)	1.0508 (3)	0.2980 (4)	0.0295 (9)
N1	0.3699 (3)	0.9263 (2)	0.2626 (2)	0.0179 (6)
C7	0.5319 (5)	0.9636 (3)	0.2328 (3)	0.0254 (8)
H7A	0.6120	0.9123	0.2458	0.031*
H7B	0.5270	0.9801	0.1552	0.031*
C2	0.3635 (5)	0.9171 (4)	0.3857 (3)	0.0304 (9)
H2A	0.3699	0.9817	0.4192	0.037*
H2B	0.4545	0.8786	0.4154	0.037*
C6	0.0766 (5)	0.9545 (3)	0.2549 (4)	0.0328 (9)
H6A	0.0331	1.0004	0.3062	0.039*
H6B	0.0000	0.9485	0.1916	0.039*
C5	0.1811 (5)	0.7878 (3)	0.2331 (3)	0.0284 (9)
H5A	0.1173	0.7831	0.1637	0.034*
H5B	0.1883	0.7228	0.2657	0.034*
C4	0.2072 (5)	0.8675 (3)	0.4119 (3)	0.0275 (8)
H4A	0.2297	0.8033	0.4439	0.033*
H4B	0.1526	0.9066	0.4646	0.033*
C1	0.2367 (5)	0.9922 (4)	0.2188 (4)	0.0395 (11)
H1A	0.2344	0.9939	0.1391	0.047*
H1B	0.2553	1.0585	0.2460	0.047*
N3	0.6229 (5)	1.1147 (3)	0.3508 (3)	0.0417 (10)
C3	0.3479 (5)	0.8252 (3)	0.2136 (4)	0.0338 (10)
H3A	0.4283	0.7809	0.2472	0.041*
H3B	0.3620	0.8277	0.1353	0.041*
H10	0.009 (6)	0.840 (4)	0.329 (4)	0.032 (12)*

	U11	U22	U33	U12	U13	U23
Co1	0.0229 (3)	0.0220 (3)	0.0222 (3)	0.0000 (2)	0.00147 (19)	−0.00076 (19)
Cl2	0.0287 (5)	0.0414 (6)	0.0211 (4)	−0.0016 (4)	0.0011 (3)	−0.0027 (4)
Cl3	0.0320 (5)	0.0209 (5)	0.0305 (5)	−0.0024 (4)	0.0066 (4)	−0.0011 (4)
Cl4	0.0302 (5)	0.0298 (5)	0.0366 (5)	−0.0057 (4)	0.0045 (4)	0.0038 (4)
Cl1	0.0283 (5)	0.0377 (6)	0.0312 (5)	0.0063 (4)	0.0012 (4)	0.0073 (4)
N2	0.0190 (15)	0.0256 (17)	0.0257 (15)	−0.0021 (13)	0.0063 (12)	−0.0035 (13)
C8	0.027 (2)	0.023 (2)	0.038 (2)	−0.0038 (17)	−0.0002 (16)	0.0084 (17)
N1	0.0182 (14)	0.0165 (15)	0.0190 (14)	−0.0004 (12)	0.0023 (11)	−0.0008 (11)
C7	0.0220 (18)	0.026 (2)	0.0294 (19)	−0.0053 (15)	0.0074 (15)	0.0016 (15)
C2	0.0255 (19)	0.047 (3)	0.0185 (17)	−0.0080 (18)	0.0007 (14)	−0.0004 (17)
C6	0.025 (2)	0.031 (2)	0.043 (2)	0.0093 (17)	0.0031 (17)	0.0025 (18)
C5	0.0262 (19)	0.026 (2)	0.034 (2)	−0.0063 (16)	0.0053 (16)	−0.0129 (16)
C4	0.030 (2)	0.035 (2)	0.0182 (16)	−0.0063 (17)	0.0057 (15)	−0.0023 (15)
C1	0.028 (2)	0.031 (2)	0.059 (3)	0.0022 (18)	−0.005 (2)	0.020 (2)
N3	0.052 (2)	0.028 (2)	0.044 (2)	−0.0136 (18)	−0.0076 (18)	0.0070 (17)
C3	0.034 (2)	0.026 (2)	0.044 (2)	−0.0080 (17)	0.0192 (19)	−0.0181 (18)

Co1—Cl1	2.2749 (12)	C2—C4	1.516 (5)
Co1—Cl4	2.2808 (12)	C2—H2A	0.9700
Co1—Cl2	2.2809 (11)	C2—H2B	0.9700
Co1—Cl3	2.2910 (12)	C6—C1	1.518 (6)
N2—C6	1.487 (5)	C6—H6A	0.9700
N2—C4	1.493 (5)	C6—H6B	0.9700
N2—C5	1.496 (5)	C5—C3	1.510 (6)
N2—H10	0.86 (5)	C5—H5A	0.9700
C8—N3	1.125 (6)	C5—H5B	0.9700
C8—C7	1.469 (6)	C4—H4A	0.9700
N1—C1	1.495 (5)	C4—H4B	0.9700
N1—C7	1.505 (4)	C1—H1A	0.9700
N1—C3	1.506 (5)	C1—H1B	0.9700
N1—C2	1.510 (5)	C3—H3A	0.9700
C7—H7A	0.9700	C3—H3B	0.9700
C7—H7B	0.9700
Cl1—Co1—Cl4	113.26 (5)	N2—C6—C1	109.0 (3)
Cl1—Co1—Cl2	107.64 (5)	N2—C6—H6A	109.9
Cl4—Co1—Cl2	110.73 (5)	C1—C6—H6A	109.9
Cl1—Co1—Cl3	113.85 (5)	N2—C6—H6B	109.9
Cl4—Co1—Cl3	107.70 (4)	C1—C6—H6B	109.9
Cl2—Co1—Cl3	103.21 (4)	H6A—C6—H6B	108.3
C6—N2—C4	110.1 (3)	N2—C5—C3	109.2 (3)
C6—N2—C5	110.4 (3)	N2—C5—H5A	109.8
C4—N2—C5	108.9 (3)	C3—C5—H5A	109.8
C6—N2—H10	105 (3)	N2—C5—H5B	109.8
C4—N2—H10	106 (3)	C3—C5—H5B	109.8
C5—N2—H10	116 (3)	H5A—C5—H5B	108.3
N3—C8—C7	176.4 (5)	N2—C4—C2	109.0 (3)
C1—N1—C7	111.4 (3)	N2—C4—H4A	109.9
C1—N1—C3	109.8 (3)	C2—C4—H4A	109.9
C7—N1—C3	107.4 (3)	N2—C4—H4B	109.9
C1—N1—C2	109.3 (3)	C2—C4—H4B	109.9
C7—N1—C2	111.0 (3)	H4A—C4—H4B	108.3
C3—N1—C2	107.8 (3)	N1—C1—C6	109.7 (3)
C8—C7—N1	111.0 (3)	N1—C1—H1A	109.7
C8—C7—H7A	109.4	C6—C1—H1A	109.7
N1—C7—H7A	109.4	N1—C1—H1B	109.7
C8—C7—H7B	109.4	C6—C1—H1B	109.7
N1—C7—H7B	109.4	H1A—C1—H1B	108.2
H7A—C7—H7B	108.0	N1—C3—C5	109.5 (3)
N1—C2—C4	109.5 (3)	N1—C3—H3A	109.8
N1—C2—H2A	109.8	C5—C3—H3A	109.8
C4—C2—H2A	109.8	N1—C3—H3B	109.8
N1—C2—H2B	109.8	C5—C3—H3B	109.8
C4—C2—H2B	109.8	H3A—C3—H3B	108.2
H2A—C2—H2B	108.2

D—H···A	D—H	H···A	D···A	D—H···A
N2—H10···Cl3i	0.86 (5)	2.52 (5)	3.236 (3)	140 (4)
N2—H10···Cl2ii	0.86 (5)	2.65 (5)	3.225 (3)	125 (4)
C3—H3B···Cl1iii	0.97	2.74	3.647 (4)	156
C7—H7A···Cl2iii	0.97	2.58	3.492 (4)	156
C2—H2A···Cl3iv	0.97	2.73	3.543 (4)	142
C3—H3A···N3v	0.97	2.58	2.983 (4)	105

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H10⋯Cl3i	0.86 (5)	2.52 (5)	3.236 (3)	140 (4)
N2—H10⋯Cl2ii	0.86 (5)	2.65 (5)	3.225 (3)	125 (4)
C3—H3B⋯Cl1iii	0.97	2.74	3.647 (4)	156
C7—H7A⋯Cl2iii	0.97	2.58	3.492 (4)	156
C2—H2A⋯Cl3iv	0.97	2.73	3.543 (4)	142
C3—H3A⋯N3v	0.97	2.58	2.983 (4)	105

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