Cyano-methanaminium perchlorate.

In the crystal of the title salt, C2H5N2(+)·ClO4(-), the cations and anions are connected via N-H⋯O and C-H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For general background, see: Haertling (1999 ▶); Homes et al. (2001 ▶). For a related structure, see: Han & Zhang (2010 ▶).

Experimental

Crystal data

C2H5N2 +·ClO4 −

M = 156.53

Orthorhombic,

a = 9.908 (2) Å

b = 10.398 (2) Å

c = 11.176 (2) Å

V = 1151.4 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.61 mm−1

T = 293 K

0.20 × 0.19 × 0.18 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.88, T max = 0.90

10965 measured reflections

1321 independent reflections

1151 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.096

S = 1.12

1321 reflections

84 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.37 e Å−3

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

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812047782/xu5654sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812047782/xu5654Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812047782/xu5654Isup3.cml

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

C2H5N2+·ClO4−	F(000) = 640
Mr = 156.53	Dx = 1.806 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1321 reflections
a = 9.908 (2) Å	θ = 2.6–27.5°
b = 10.398 (2) Å	µ = 0.61 mm−1
c = 11.176 (2) Å	T = 293 K
V = 1151.4 (4) Å3	Prism, colorless
Z = 8	0.20 × 0.19 × 0.18 mm

Rigaku Mercury2 diffractometer	1321 independent reflections
Radiation source: fine-focus sealed tube	1151 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.4°
CCD_Profile_fitting scans	h = −12→12
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −13→13
Tmin = 0.88, Tmax = 0.90	l = −14→14
10965 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)] = 0.034	H-atom parameters constrained
wR(F2) = 0.096	w = 1/[σ2(Fo2) + (0.0373P)2 + 0.8373P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max = 0.002
1321 reflections	Δρmax = 0.40 e Å−3
84 parameters	Δρmin = −0.37 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.072 (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
Cl1	0.24234 (4)	0.55298 (4)	0.39030 (4)	0.0262 (2)
N1	0.38874 (19)	0.80122 (18)	0.60010 (15)	0.0338 (4)
H1C	0.3343	0.8461	0.6478	0.051*
H1D	0.3423	0.7726	0.5374	0.051*
H1E	0.4558	0.8514	0.5750	0.051*
N2	0.5768 (2)	0.7581 (2)	0.85728 (18)	0.0503 (6)
O1	0.30000 (17)	0.51248 (16)	0.27907 (14)	0.0432 (4)
O2	0.10533 (16)	0.50926 (18)	0.39645 (16)	0.0485 (5)
O3	0.31737 (19)	0.50020 (19)	0.48743 (16)	0.0521 (5)
O4	0.24459 (16)	0.69160 (15)	0.39638 (15)	0.0414 (5)
C1	0.4448 (2)	0.6911 (2)	0.6667 (2)	0.0354 (5)
H1A	0.3718	0.6343	0.6900	0.042*
H1B	0.5049	0.6432	0.6147	0.042*
C2	0.5189 (2)	0.7311 (2)	0.77361 (19)	0.0335 (5)

	U11	U22	U33	U12	U13	U23
Cl1	0.0279 (3)	0.0258 (3)	0.0249 (3)	0.00019 (17)	−0.00002 (18)	−0.00046 (17)
N1	0.0368 (10)	0.0363 (10)	0.0283 (9)	−0.0023 (7)	−0.0062 (7)	−0.0005 (7)
N2	0.0541 (12)	0.0613 (15)	0.0354 (11)	−0.0057 (11)	−0.0128 (9)	−0.0011 (10)
O1	0.0516 (10)	0.0449 (9)	0.0331 (9)	0.0040 (8)	0.0122 (7)	−0.0064 (7)
O2	0.0319 (9)	0.0492 (10)	0.0643 (12)	−0.0084 (7)	0.0085 (8)	−0.0033 (8)
O3	0.0638 (12)	0.0515 (10)	0.0409 (10)	0.0079 (9)	−0.0182 (9)	0.0077 (8)
O4	0.0529 (11)	0.0247 (9)	0.0466 (11)	0.0000 (6)	−0.0076 (8)	−0.0046 (6)
C1	0.0415 (11)	0.0306 (11)	0.0341 (11)	−0.0017 (9)	−0.0089 (10)	−0.0009 (9)
C2	0.0308 (10)	0.0386 (11)	0.0310 (11)	−0.0019 (9)	−0.0016 (8)	0.0028 (9)

Cl1—O3	1.4256 (17)	N1—H1D	0.8900
Cl1—O1	1.4314 (16)	N1—H1E	0.8900
Cl1—O2	1.4333 (17)	N2—C2	1.133 (3)
Cl1—O4	1.4431 (16)	C1—C2	1.462 (3)
N1—C1	1.475 (3)	C1—H1A	0.9700
N1—H1C	0.8900	C1—H1B	0.9700
O3—Cl1—O1	109.87 (11)	H1C—N1—H1E	109.5
O3—Cl1—O2	109.59 (12)	H1D—N1—H1E	109.5
O1—Cl1—O2	109.04 (11)	C2—C1—N1	112.37 (18)
O3—Cl1—O4	109.92 (11)	C2—C1—H1A	109.1
O1—Cl1—O4	109.18 (10)	N1—C1—H1A	109.1
O2—Cl1—O4	109.22 (10)	C2—C1—H1B	109.1
C1—N1—H1C	109.5	N1—C1—H1B	109.1
C1—N1—H1D	109.5	H1A—C1—H1B	107.9
H1C—N1—H1D	109.5	N2—C2—C1	177.8 (2)
C1—N1—H1E	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···O1i	0.89	2.10	2.920 (2)	152
N1—H1D···O4	0.89	2.03	2.919 (2)	175
N1—H1E···O2ii	0.89	2.10	2.914 (3)	152
C1—H1A···O1iii	0.97	2.49	3.456 (3)	172
C1—H1B···O3iv	0.97	2.57	3.532 (3)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1C⋯O1i	0.89	2.10	2.920 (2)	152
N1—H1D⋯O4	0.89	2.03	2.919 (2)	175
N1—H1E⋯O2ii	0.89	2.10	2.914 (3)	152
C1—H1A⋯O1iii	0.97	2.49	3.456 (3)	172
C1—H1B⋯O3iv	0.97	2.57	3.532 (3)	169

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