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

In the crystal structure of the title compound, (C(8)H(15)N(3))[MnCl(4)], the Mn atom is coordinated by four chloride ligands in a slightly distorted tetra-hedral geometry. Each [MnCl(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].

Related literature

For similar crystal structures of related compounds, see: Al-Far et al. (2008 ▶); Cai (2010 ▶). For the use of DABCO (1,4-diaza­bicyclo­[2.2.2]octa­ne) and its derivatives, see: Basaviah et al. (2003 ▶); Zhang, Cheng et al. (2009 ▶) and for its ferroelectric properties, see: Zhang, Ye et al. (2009 ▶); Ye et al. (2009 ▶).

Experimental

Crystal data

(C8H15N3)[MnCl4]

M = 349.97

Monoclinic,

a = 8.373 (3) Å

b = 13.713 (6) Å

c = 12.188 (5) Å

β = 93.657 (8)°

V = 1396.6 (10) Å3

Z = 4

Mo Kα radiation

μ = 1.69 mm−1

T = 298 K

0.2 × 0.2 × 0.2 mm

Data collection

Rigaku Mercury CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.713, T max = 0.721

14901 measured reflections

3181 independent reflections

2788 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.103

S = 1.11

3181 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.66 e Å−3

Δρmin = −0.52 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/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681004047X/im2229sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681004047X/im2229Isup2.hkl

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

(C8H15N3)[MnCl4]	F(000) = 708
Mr = 349.97	Dx = 1.664 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4022 reflections
a = 8.373 (3) Å	θ = 2.2–27.5°
b = 13.713 (6) Å	µ = 1.69 mm−1
c = 12.188 (5) Å	T = 298 K
β = 93.657 (8)°	PRISM, colourless
V = 1396.6 (10) Å3	0.2 × 0.2 × 0.2 mm
Z = 4

Rigaku Mercury CCD diffractometer	3181 independent reflections
Radiation source: fine-focus sealed tube	2788 reflections with I > 2σ(I)
graphite	Rint = 0.035
Detector resolution: 28.5714 pixels mm-1	θmax = 27.5°, θmin = 2.2°
ω scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −17→17
Tmin = 0.713, Tmax = 0.721	l = −15→15
14901 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) = 0.103	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.061P)2 + 0.074P] where P = (Fo2 + 2Fc2)/3
3181 reflections	(Δ/σ)max = 0.001
145 parameters	Δρmax = 0.66 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
Mn1	0.22628 (4)	0.23007 (3)	0.99138 (3)	0.02877 (13)
Cl3	0.19440 (7)	0.39665 (4)	1.03991 (5)	0.03248 (16)
Cl2	0.22006 (7)	0.23950 (5)	0.79599 (5)	0.03590 (17)
Cl4	−0.00249 (7)	0.14312 (4)	1.04423 (5)	0.03416 (16)
Cl1	0.47527 (7)	0.16000 (5)	1.05057 (5)	0.03580 (16)
N1	0.8938 (2)	0.35643 (14)	0.19241 (15)	0.0270 (4)
H1C	0.9919	0.3329	0.1718	0.032*
N2	0.6277 (2)	0.42613 (13)	0.23649 (14)	0.0218 (4)
C8	0.4225 (3)	0.55167 (18)	0.2010 (2)	0.0324 (5)
C3	0.9196 (3)	0.45395 (19)	0.2452 (2)	0.0371 (6)
H3A	0.9625	0.4991	0.1934	0.044*
H3B	0.9956	0.4484	0.3083	0.044*
C7	0.4681 (3)	0.46467 (17)	0.26521 (19)	0.0294 (5)
H7A	0.3875	0.4146	0.2515	0.035*
H7B	0.4721	0.4805	0.3429	0.035*
C1	0.7902 (3)	0.36583 (19)	0.08854 (19)	0.0308 (5)
H1A	0.7673	0.3018	0.0577	0.037*
H1B	0.8451	0.4036	0.0352	0.037*
C2	0.6363 (3)	0.4158 (2)	0.11339 (18)	0.0325 (5)
H2A	0.5458	0.3780	0.0835	0.039*
H2B	0.6314	0.4798	0.0793	0.039*
C5	0.8155 (3)	0.28891 (18)	0.2681 (2)	0.0321 (5)
H5A	0.8783	0.2851	0.3376	0.039*
H5B	0.8088	0.2241	0.2363	0.039*
N3	0.3839 (3)	0.61644 (16)	0.1482 (2)	0.0457 (6)
C6	0.6493 (3)	0.32604 (19)	0.2868 (2)	0.0368 (6)
H6A	0.5699	0.2817	0.2535	0.044*
H6B	0.6347	0.3292	0.3650	0.044*
C4	0.7606 (3)	0.4915 (2)	0.2813 (2)	0.0419 (6)
H4A	0.7624	0.4928	0.3609	0.050*
H4B	0.7427	0.5574	0.2545	0.050*

	U11	U22	U33	U12	U13	U23
Mn1	0.0269 (2)	0.0284 (2)	0.0308 (2)	0.00024 (14)	0.00125 (16)	−0.00150 (14)
Cl3	0.0358 (3)	0.0263 (3)	0.0360 (3)	−0.0027 (2)	0.0074 (3)	−0.0003 (2)
Cl2	0.0317 (3)	0.0471 (4)	0.0287 (3)	−0.0015 (3)	0.0010 (2)	−0.0043 (2)
Cl4	0.0312 (3)	0.0325 (3)	0.0390 (3)	−0.0035 (2)	0.0038 (3)	0.0021 (2)
Cl1	0.0310 (3)	0.0426 (3)	0.0339 (3)	0.0066 (2)	0.0024 (2)	0.0076 (3)
N1	0.0216 (9)	0.0309 (10)	0.0289 (10)	0.0021 (8)	0.0046 (8)	0.0022 (8)
N2	0.0219 (9)	0.0209 (9)	0.0227 (9)	−0.0001 (7)	0.0020 (7)	0.0008 (7)
C8	0.0296 (12)	0.0288 (12)	0.0384 (13)	0.0062 (10)	−0.0013 (10)	−0.0090 (11)
C3	0.0262 (12)	0.0370 (13)	0.0478 (15)	−0.0073 (10)	0.0017 (11)	−0.0057 (11)
C7	0.0247 (11)	0.0304 (11)	0.0337 (12)	0.0037 (9)	0.0068 (10)	−0.0017 (10)
C1	0.0312 (12)	0.0363 (13)	0.0252 (11)	0.0056 (10)	0.0037 (10)	0.0001 (9)
C2	0.0284 (12)	0.0468 (14)	0.0223 (11)	0.0065 (10)	0.0012 (9)	0.0013 (10)
C5	0.0283 (12)	0.0326 (12)	0.0361 (13)	0.0055 (10)	0.0066 (10)	0.0126 (10)
N3	0.0541 (15)	0.0317 (12)	0.0498 (14)	0.0123 (11)	−0.0081 (12)	−0.0093 (11)
C6	0.0364 (14)	0.0327 (12)	0.0430 (14)	0.0080 (10)	0.0148 (12)	0.0168 (11)
C4	0.0290 (13)	0.0350 (13)	0.0605 (17)	−0.0022 (11)	−0.0067 (12)	−0.0192 (13)

Mn1—Cl1	2.3661 (10)	C3—H3B	0.9700
Mn1—Cl3	2.3789 (11)	C7—H7A	0.9700
Mn1—Cl4	2.3798 (10)	C7—H7B	0.9700
Mn1—Cl2	2.3822 (12)	C1—C2	1.507 (3)
N1—C5	1.488 (3)	C1—H1A	0.9700
N1—C3	1.494 (3)	C1—H1B	0.9700
N1—C1	1.494 (3)	C2—H2A	0.9700
N1—H1C	0.9325	C2—H2B	0.9700
N2—C7	1.500 (3)	C5—C6	1.512 (3)
N2—C4	1.504 (3)	C5—H5A	0.9700
N2—C6	1.509 (3)	C5—H5B	0.9700
N2—C2	1.513 (3)	C6—H6A	0.9700
C8—N3	1.132 (3)	C6—H6B	0.9700
C8—C7	1.464 (3)	C4—H4A	0.9700
C3—C4	1.518 (4)	C4—H4B	0.9700
C3—H3A	0.9700
Cl1—Mn1—Cl3	115.14 (3)	N1—C1—C2	109.07 (18)
Cl1—Mn1—Cl4	115.01 (4)	N1—C1—H1A	109.9
Cl3—Mn1—Cl4	107.98 (3)	C2—C1—H1A	109.9
Cl1—Mn1—Cl2	106.83 (3)	N1—C1—H1B	109.9
Cl3—Mn1—Cl2	101.58 (3)	C2—C1—H1B	109.9
Cl4—Mn1—Cl2	109.34 (3)	H1A—C1—H1B	108.3
C5—N1—C3	110.32 (19)	C1—C2—N2	109.67 (18)
C5—N1—C1	108.90 (19)	C1—C2—H2A	109.7
C3—N1—C1	110.36 (19)	N2—C2—H2A	109.7
C5—N1—H1C	112.5	C1—C2—H2B	109.7
C3—N1—H1C	108.7	N2—C2—H2B	109.7
C1—N1—H1C	106.0	H2A—C2—H2B	108.2
C7—N2—C4	110.81 (18)	N1—C5—C6	109.26 (18)
C7—N2—C6	108.12 (17)	N1—C5—H5A	109.8
C4—N2—C6	109.14 (19)	C6—C5—H5A	109.8
C7—N2—C2	111.31 (17)	N1—C5—H5B	109.8
C4—N2—C2	109.57 (19)	C6—C5—H5B	109.8
C6—N2—C2	107.82 (18)	H5A—C5—H5B	108.3
N3—C8—C7	177.1 (3)	N2—C6—C5	109.40 (19)
N1—C3—C4	108.8 (2)	N2—C6—H6A	109.8
N1—C3—H3A	109.9	C5—C6—H6A	109.8
C4—C3—H3A	109.9	N2—C6—H6B	109.8
N1—C3—H3B	109.9	C5—C6—H6B	109.8
C4—C3—H3B	109.9	H6A—C6—H6B	108.2
H3A—C3—H3B	108.3	N2—C4—C3	109.6 (2)
C8—C7—N2	111.60 (19)	N2—C4—H4A	109.8
C8—C7—H7A	109.3	C3—C4—H4A	109.8
N2—C7—H7A	109.3	N2—C4—H4B	109.8
C8—C7—H7B	109.3	C3—C4—H4B	109.8
N2—C7—H7B	109.3	H4A—C4—H4B	108.2
H7A—C7—H7B	108.0
C5—N1—C3—C4	−54.9 (3)	C3—N1—C5—C6	65.2 (3)
C1—N1—C3—C4	65.5 (3)	C1—N1—C5—C6	−56.1 (3)
C4—N2—C7—C8	72.5 (2)	C7—N2—C6—C5	−174.9 (2)
C6—N2—C7—C8	−167.9 (2)	C4—N2—C6—C5	−54.3 (3)
C2—N2—C7—C8	−49.7 (3)	C2—N2—C6—C5	64.6 (3)
C5—N1—C1—C2	66.0 (2)	N1—C5—C6—N2	−8.3 (3)
C3—N1—C1—C2	−55.2 (3)	C7—N2—C4—C3	−176.7 (2)
N1—C1—C2—N2	−8.3 (3)	C6—N2—C4—C3	64.4 (3)
C7—N2—C2—C1	−173.2 (2)	C2—N2—C4—C3	−53.5 (3)
C4—N2—C2—C1	63.9 (3)	N1—C3—C4—N2	−8.8 (3)
C6—N2—C2—C1	−54.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···Cl2i	0.93	2.56	3.217 (2)	128
N1—H1C···Cl3ii	0.93	2.56	3.270 (2)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1C⋯Cl2i	0.93	2.56	3.217 (2)	128
N1—H1C⋯Cl3ii	0.93	2.56	3.270 (2)	133

Symmetry codes: (i) ; (ii) .