Redetermination of 3-(ammonio-meth-yl)pyridinium dichloride.

The crystal structure of the title compound, C(6)H(10)N(2) (2+)·2Cl(-), has been reported previously in the non-standard setting P2(1)/a [Genet (1965 ▶). Bull. Soc. Fr. Miner. Crist.88, 463-470], with an R value of 0.16. The current redetermination improves significantly the precision of the geometric parameters. In the crystal packing, cations and anions are linked by inter-molecular N-H⋯Cl and C-H⋯Cl hydrogen bonds into a three-dimensional network.

Related literature

For related structures, see: Genet (1965 ▶); Chtioui & Jouini (2004 ▶); Long et al. (1997 ▶).

Experimental

Crystal data

C6H10N2 2+·2Cl−

M = 181.06

Monoclinic,

a = 4.5874 (9) Å

b = 12.650 (3) Å

c = 14.814 (3) Å

β = 93.61 (3)°

V = 857.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.69 mm−1

T = 293 K

0.50 × 0.45 × 0.15 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.720, T max = 0.909

8831 measured reflections

1961 independent reflections

1684 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.076

S = 1.08

1961 reflections

92 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.19 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 (Sheldrick, 2008 ▶); software used to prepare material for publication: PRPKAPPA (Ferguson, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809025859/rz2346sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025859/rz2346Isup2.hkl

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

C6H10N22+·2Cl−	F(000) = 376
Mr = 181.06	Dx = 1.402 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8048 reflections
a = 4.5874 (9) Å	θ = 3.1–27.5°
b = 12.650 (3) Å	µ = 0.69 mm−1
c = 14.814 (3) Å	T = 293 K
β = 93.61 (3)°	Prism, colourless
V = 857.9 (3) Å3	0.50 × 0.45 × 0.15 mm
Z = 4

Rigaku SCXmini diffractometer	1961 independent reflections
Radiation source: fine-focus sealed tube	1684 reflections with I > 2σ(I)
graphite	Rint = 0.035
Detector resolution: 13.662 pixels mm-1	θmax = 27.5°, θmin = 3.2°
CCD_Profile_fitting scans	h = −5→5
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −16→16
Tmin = 0.720, Tmax = 0.909	l = −19→19
8831 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) = 0.076	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0293P)2 + 0.274P] where P = (Fo2 + 2Fc2)/3
1961 reflections	(Δ/σ)max = 0.001
92 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.19 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
Cl2	0.34023 (9)	0.98847 (3)	0.37672 (3)	0.03348 (13)
N1	0.9075 (3)	0.64924 (10)	−0.01920 (10)	0.0333 (3)
H1A	0.7885	0.6098	0.0120	0.050*
H1B	0.9905	0.6091	−0.0598	0.050*
H1C	0.8058	0.7007	−0.0474	0.050*
C6	1.1364 (4)	0.69588 (14)	0.04332 (13)	0.0365 (4)
H6A	1.2888	0.7253	0.0084	0.044*
H6B	1.2231	0.6405	0.0815	0.044*
C1	1.1087 (4)	0.88417 (13)	0.08977 (12)	0.0337 (4)
H1	1.2349	0.9000	0.0449	0.040*
C5	0.8274 (4)	0.94441 (14)	0.20641 (12)	0.0370 (4)
H5	0.7619	1.0005	0.2403	0.044*
C2	1.0214 (3)	0.78119 (13)	0.10227 (11)	0.0293 (4)
C4	0.7351 (4)	0.84350 (14)	0.22213 (12)	0.0371 (4)
H4	0.6060	0.8304	0.2668	0.045*
C3	0.8357 (4)	0.76140 (14)	0.17102 (12)	0.0349 (4)
H3	0.7788	0.6924	0.1826	0.042*
Cl1	0.40819 (11)	0.14752 (3)	0.10233 (3)	0.04427 (15)
N2	1.0124 (3)	0.96146 (11)	0.14194 (10)	0.0367 (4)
H2	1.0724	1.0249	0.1336	0.044*

	U11	U22	U33	U12	U13	U23
Cl2	0.0384 (2)	0.0291 (2)	0.0340 (2)	−0.00167 (16)	0.01032 (17)	−0.00133 (16)
N1	0.0389 (8)	0.0256 (7)	0.0362 (8)	0.0047 (6)	0.0099 (6)	−0.0021 (6)
C6	0.0310 (9)	0.0315 (9)	0.0479 (11)	0.0040 (7)	0.0086 (8)	−0.0028 (8)
C1	0.0347 (9)	0.0314 (9)	0.0352 (9)	0.0001 (7)	0.0041 (7)	0.0029 (7)
C5	0.0440 (10)	0.0354 (10)	0.0311 (9)	0.0044 (8)	−0.0011 (8)	−0.0071 (7)
C2	0.0260 (8)	0.0284 (8)	0.0331 (9)	0.0020 (6)	−0.0008 (7)	−0.0010 (7)
C4	0.0406 (10)	0.0407 (10)	0.0306 (9)	−0.0030 (8)	0.0064 (8)	−0.0032 (7)
C3	0.0390 (10)	0.0297 (9)	0.0363 (10)	−0.0038 (7)	0.0044 (8)	0.0005 (7)
Cl1	0.0486 (3)	0.0305 (2)	0.0547 (3)	0.00301 (18)	0.0108 (2)	0.00943 (19)
N2	0.0462 (9)	0.0237 (7)	0.0397 (9)	−0.0029 (6)	−0.0014 (7)	0.0013 (6)

N1—C6	1.478 (2)	C1—H1	0.9300
N1—H1A	0.8900	C5—N2	1.334 (2)
N1—H1B	0.8900	C5—C4	1.369 (3)
N1—H1C	0.8900	C5—H5	0.9300
C6—C2	1.504 (2)	C2—C3	1.391 (2)
C6—H6A	0.9700	C4—C3	1.382 (2)
C6—H6B	0.9700	C4—H4	0.9300
C1—N2	1.338 (2)	C3—H3	0.9300
C1—C2	1.379 (2)	N2—H2	0.8600
C6—N1—H1A	109.5	N2—C5—C4	119.33 (16)
C6—N1—H1B	109.5	N2—C5—H5	120.3
H1A—N1—H1B	109.5	C4—C5—H5	120.3
C6—N1—H1C	109.5	C1—C2—C3	117.69 (16)
H1A—N1—H1C	109.5	C1—C2—C6	118.97 (16)
H1B—N1—H1C	109.5	C3—C2—C6	123.31 (15)
N1—C6—C2	112.88 (13)	C5—C4—C3	119.34 (17)
N1—C6—H6A	109.0	C5—C4—H4	120.3
C2—C6—H6A	109.0	C3—C4—H4	120.3
N1—C6—H6B	109.0	C4—C3—C2	120.47 (16)
C2—C6—H6B	109.0	C4—C3—H3	119.8
H6A—C6—H6B	107.8	C2—C3—H3	119.8
N2—C1—C2	120.23 (16)	C5—N2—C1	122.89 (15)
N2—C1—H1	119.9	C5—N2—H2	118.6
C2—C1—H1	119.9	C1—N2—H2	118.6

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl2i	0.89	2.35	3.1914 (16)	157
N1—H1B···Cl2ii	0.89	2.27	3.1206 (16)	159
N1—H1C···Cl1iii	0.89	2.28	3.1622 (16)	170
N2—H2···Cl1iv	0.86	2.25	3.0520 (16)	154
C3—H3···Cl2i	0.93	2.77	3.606 (2)	150
C6—H6A···Cl1v	0.97	2.74	3.676 (2)	163
C6—H6B···Cl2vi	0.97	2.82	3.700 (2)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl2i	0.89	2.35	3.1914 (16)	157
N1—H1B⋯Cl2ii	0.89	2.27	3.1206 (16)	159
N1—H1C⋯Cl1iii	0.89	2.28	3.1622 (16)	170
N2—H2⋯Cl1iv	0.86	2.25	3.0520 (16)	154
C3—H3⋯Cl2i	0.93	2.77	3.606 (2)	150
C6—H6A⋯Cl1v	0.97	2.74	3.676 (2)	163
C6—H6B⋯Cl2vi	0.97	2.82	3.700 (2)	152

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