o-Phenyl-enediaminium chloride nitrate.

In the title mol-ecular salt, C6H10N2 (2+)·NO3 (-)·Cl(-), the complete cation is generated by a crystallographic mirror plane. The complete nitrate ion is also generated by reflection, with the N atom and one O atom lying on the mirror plane; the chloride ion also lies on the reflection plane. In the crystal, the components are linked by N-H⋯Cl and N-H⋯(N,O) hydrogen bonds, forming (001) layers with the benzene rings projecting into the inter-layer regions. The layers are linked by weak C-H⋯O hydrogen bonds, generating a three-dimensional network.

Related literature

For background to inorganic–organic hybrid compounds, see: Bringley & Rajeswaram (2006 ▶); Dai et al. (2002 ▶). For reference structural data, see: Riahi et al. (2012 ▶); Engh & Huber (1991 ▶).

Experimental

Crystal data

C6H10N2 2+·Cl−·NO3 −

M = 207.61

Orthorhombic,

a = 7.3695 (5) Å

b = 8.2367 (5) Å

c = 14.2398 (7) Å

V = 864.36 (8) Å3

Z = 4

Ag Kα radiation

λ = 0.56085 Å

μ = 0.22 mm−1

T = 100 K

0.27 × 0.20 × 0.15 mm

Data collection

Bruker Photon100 CMOS detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.751, T max = 0.967

26823 measured reflections

812 independent reflections

812 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.053

S = 0.80

812 reflections

66 parameters

12 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.26 e Å−3

Data collection: COLLECT (Bruker, 2004 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: MoPro (Jelsch et al., 2005 ▶); molecular graphics: DIAMOND (Brandenburg, 1998 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813007447/hb7052sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813007447/hb7052Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813007447/hb7052Isup3.cml

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

C6H10N22+·Cl−·NO3−	F(000) = 432
Mr = 207.61	Dx = 1.596 Mg m−3
Orthorhombic, Pnma	Ag Kα radiation, λ = 0.56085 Å
Hall symbol: -P 2ac 2n	Cell parameters from 64 reflections
a = 7.3695 (5) Å	θ = 3.1–20.3°
b = 8.2367 (5) Å	µ = 0.22 mm−1
c = 14.2398 (7) Å	T = 100 K
V = 864.36 (8) Å3	Prismatic, yellow
Z = 4	0.27 × 0.20 × 0.15 mm

Bruker Photon100 CMOS detector diffractometer	812 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.049
ω scans	θmax = 19.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = 0→8
Tmin = 0.751, Tmax = 0.967	k = 0→9
26823 measured reflections	l = 0→16
812 independent 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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.053	H atoms treated by a mixture of independent and constrained refinement
S = 0.80	w = 1/[σ2(Fo2) + (0.P)2 + 2.3P] where P = (Fo2 + 2Fc2)/3
812 reflections	(Δ/σ)max = −0.002
66 parameters	Δρmax = 0.27 e Å−3
12 restraints	Δρmin = −0.26 e Å−3

Refinement. Refinement of F2 against reflections. The threshold expression of F2 > 2sigma(F2) is used for calculating R-factors(gt) 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	0.84182 (9)	0.25000	0.34646 (4)	0.00937 (9)
N1	0.2199 (3)	0.75000	0.3046 (2)	0.0091 (3)
O11	0.3554 (3)	0.75000	0.3614 (1)	0.0098 (3)
O10	0.1566 (2)	0.6174 (2)	0.27870 (9)	0.0143 (2)
C1	0.1707 (3)	0.3346 (2)	0.5526 (1)	0.0117 (3)
H1	0.10400	0.40337	0.60752	0.01410*
C2	0.2654 (3)	0.4193 (2)	0.4834 (1)	0.0100 (2)
H2	0.26439	0.55074	0.48291	0.01199*
C3	0.3611 (2)	0.3345 (2)	0.4152 (1)	0.0071 (2)
N3	0.4604 (2)	0.4241 (2)	0.3431 (1)	0.0083 (2)
H31	0.417 (1)	0.393 (1)	0.2766 (3)	0.01240*
H32	0.5979 (4)	0.400 (1)	0.3466 (10)	0.01240*
H34	0.443 (2)	0.5479 (3)	0.3506 (9)	0.01240*

	U11	U22	U33	U12	U13	U23
Cl1	0.0105 (3)	0.0079 (3)	0.0097 (3)	0	−0.0003 (3)	0
N1	0.011 (1)	0.006 (1)	0.010 (1)	0	−0.0011 (9)	0
O11	0.0117 (9)	0.0032 (9)	0.0145 (10)	0	−0.0032 (8)	0
O10	0.0168 (7)	0.0076 (6)	0.0184 (7)	−0.0016 (6)	−0.0052 (6)	−0.0023 (6)
C1	0.0149 (9)	0.0101 (10)	0.0102 (9)	0.0008 (8)	0.0030 (8)	−0.0012 (8)
C2	0.0128 (9)	0.0058 (9)	0.0113 (9)	0.0008 (8)	0.0011 (7)	−0.0014 (7)
C3	0.0084 (9)	0.0052 (9)	0.0079 (9)	−0.0001 (8)	0.0010 (7)	0.0003 (7)
N3	0.0099 (8)	0.0049 (7)	0.0100 (7)	−0.0008 (6)	0.0002 (6)	0.0008 (6)

N1—O10	1.243 (2)	C2—H2	1.083
N1—O11	1.284 (3)	C3—N3	1.461 (2)
C1—C2	1.395 (3)	N3—H32	1.033 (4)
C1—H1	1.083	N3—H34	1.033 (4)
C2—C3	1.389 (3)	N3—H31	1.033 (4)
O11—N1—O10	118.6 (2)	C3—N3—H32	111.2 (7)
O10—N1—O10i	122.8 (2)	C3—N3—H34	111.3 (7)
C1—C2—C3	119.8 (2)	C3—N3—H31	111.1 (6)
C1—C2—H2	120.1	H31—N3—H32	107.7 (8)
H1—C1—C2	118.4	H31—N3—H34	107.6 (9)
C2—C3—N3	119.5 (2)	H32—N3—H34	107.7 (10)
H2—C2—C3	120.1
C1—C2—C3—N3	−179.8 (2)	C2—C3—N3—H34	−2.1 (7)
H1—C1—C2—C3	176.3	C2—C3—N3—H31	−122.0 (7)
H1—C1—C2—H2	−3.7	H2—C2—C3—N3	0.2
C2—C3—N3—H32	118.0 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H34···O10	1.033 (4)	2.41 (1)	2.896 (2)	107.4 (9)
N3—H34···N1	1.033 (4)	2.429 (9)	3.263 (2)	137.1 (8)
N3—H31···Cl1ii	1.033 (4)	2.181 (4)	3.179 (2)	161.8 (5)
N3—H32···Cl1	1.033 (4)	2.183 (5)	3.156 (2)	156.2 (5)
C2—H2···O11	1.08	2.48	3.299 (2)	132
C1—H1···O10iii	1.08	2.52	3.427 (2)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H34⋯O10	1.033 (4)	2.41 (1)	2.896 (2)	107.4 (9)
N3—H34⋯N1	1.033 (4)	2.429 (9)	3.263 (2)	137.1 (8)
N3—H31⋯Cl1i	1.033 (4)	2.181 (4)	3.179 (2)	161.8 (5)
N3—H32⋯Cl1	1.033 (4)	2.183 (5)	3.156 (2)	156.2 (5)
C2—H2⋯O11	1.08	2.48	3.299 (2)	132
C1—H1⋯O10ii	1.08	2.52	3.427 (2)	141

Symmetry codes: (i) ; (ii) .