Naphthalene-1,5-diammonium dichloride

In the title compound, C₁₀H_I2N²⁺·2CI⁻, the naphthalene-1,5-diammonium ion lies on an inversion center; the asymmetric unit contains half of the cation and one Cl⁻ anion. The structure can be described as consisting of alternating layers of C₁₀H_I2N²⁺ and CI⁻ ions perpendicular to the a axis. The structure contains N—H...Cl hydrogen bonds, which build up a two-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.036
• wR factor = 0.083
• Data-to-parameter ratio = 22.7

checkCIF/PLATON results

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Computing details

Data collection: Collect (Nonius, 1997); cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997); data reduction: HKL DENZO (Otwinowski & Minor 1997) and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999) and PARST (Nardelli, 1995).

(I)

Crystal data

C10H12N2^2+·2Cl^−	F(000) = 240
Mr = 231.12	Dx = 1.454 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4491 reflections
a = 8.5766 (4) Å	θ = 1.0–30.0°
b = 5.1650 (4) Å	µ = 0.58 mm^−1
c = 12.2001 (7) Å	T = 173 K
β = 102.394 (1)°	Needle, white
V = 527.85 (6) Å^3	0.45 × 0.05 × 0.03 mm
Z = 2

Data collection

Nonius KappaCCD diffractometer	1265 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.044
Detector resolution: 9 pixels mm^-1	θmax = 29.9°, θmin = 2.4°
φ scans	h = −12→11
4124 measured reflections	k = −7→7
1523 independent reflections	l = −16→12

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.083	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0161P)^2 + 0.2248P] where P = (Fo^2 + 2Fc^2)/3
1523 reflections	(Δ/σ)max < 0.001
67 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.27 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.44779 (5)	0.21431 (7)	0.35441 (3)	0.02071 (13)
N1	0.34394 (15)	0.2116 (2)	0.08241 (11)	0.0184 (3)
C1	0.08397 (17)	0.0054 (3)	0.00288 (13)	0.0148 (3)
C2	0.17249 (17)	0.1932 (3)	0.07625 (13)	0.0156 (3)
C3	0.10277 (19)	0.3564 (3)	0.13922 (13)	0.0189 (3)
C4	−0.06309 (19)	0.3425 (3)	0.13258 (13)	0.0197 (3)
C5	−0.15455 (19)	0.1658 (3)	0.06337 (13)	0.0185 (3)
H1	−0.2639	0.1581	0.0598	0.022*
H2	−0.1108	0.4541	0.1755	0.024*
H3	0.1644	0.4765	0.1864	0.023*
H4	0.3615	0.2372	0.0139	0.035 (6)*
H5	0.391	0.0653	0.1105	0.035 (5)*
H6	0.3838	0.3435	0.1265	0.045 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0229 (2)	0.0219 (2)	0.0170 (2)	0.00300 (14)	0.00343 (15)	0.00044 (14)
N1	0.0157 (6)	0.0213 (7)	0.0174 (7)	−0.0035 (5)	0.0021 (5)	−0.0014 (5)
C1	0.0154 (7)	0.0150 (7)	0.0140 (7)	−0.0002 (5)	0.0030 (6)	0.0026 (5)
C2	0.0138 (7)	0.0175 (7)	0.0150 (7)	−0.0015 (5)	0.0019 (6)	0.0025 (6)
C3	0.0214 (8)	0.0176 (7)	0.0163 (8)	−0.0030 (6)	0.0012 (6)	−0.0013 (6)
C4	0.0221 (8)	0.0186 (8)	0.0192 (8)	0.0025 (6)	0.0059 (6)	−0.0018 (6)
C5	0.0158 (7)	0.0205 (8)	0.0194 (8)	0.0002 (6)	0.0041 (6)	0.0008 (6)

Geometric parameters (Å, º)

N1—C2	1.4593 (19)	C3—C4	1.409 (2)
N1—H4	0.89	C3—H3	0.93
N1—H5	0.89	C4—C5	1.370 (2)
N1—H6	0.89	C4—H2	0.93
C1—C1^i	1.428 (3)	C5—C1^i	1.418 (2)
C1—C2	1.424 (2)	C5—H1	0.93
C3—C2	1.362 (2)
C2—N1—H4	109.5	C1—C2—N1	118.18 (13)
C2—N1—H5	109.5	C2—C3—C4	119.74 (14)
H4—N1—H5	109.5	C2—C3—H3	120.1
C2—N1—H6	109.5	C4—C3—H3	120.1
H4—N1—H6	109.5	C5—C4—C3	120.44 (15)
H5—N1—H6	109.5	C5—C4—H2	119.8
C5^i—C1—C2	123.22 (14)	C3—C4—H2	119.8
C5^i—C1—C1^i	119.81 (17)	C4—C5—C1^i	120.58 (14)
C2—C1—C1^i	116.97 (17)	C4—C5—H1	119.7
C3—C2—C1	122.47 (14)	C1^i—C5—H1	119.7
C3—C2—N1	119.34 (13)

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N(1)—H(4)···Cl(1)^ii	0.89	2.24	3.1210 (14)	171
N(1)—H(5)···Cl(1)^iii	0.89	2.26	3.1291 (12)	164
N(1)—H(6)···Cl(1)	0.89	2.80	3.2460 (14)	113
N(1)—H(6)···Cl(1)^iv	0.89	2.38	3.1521 (12)	145

Symmetry codes: (ii) x, −y+1/2, z−1/2; (iii) −x+1, y−1/2, −z+1/2; (iv) −x+1, y+1/2, −z+1/2.