3-Allyl-1-methyl-1H-benzotriazol-3-ium iodide.

In the crystal structure of 1-methyl-3-allyl benzotriazolium iodide, C(10)H(12)N(3) (+)·I(-), centrosymmetric dimers of coplanar cations are π-stacked with an inter-planar distance of 3.453 (6) Å. The iodide anions are situated above and below the formally positive charged triazolium rings.

Related literature

For information on the Cambridge Structural Database, see: Allen (2002 ▶). For structural investigations of related compounds, see: Boche et al. (1996 ▶); Mouhib et al. (2011 ▶). For general information on π-stacking, see: Wright (1995 ▶).

Experimental

Crystal data

C10H12N3 +·I−

M = 301.13

Triclinic,

a = 7.8839 (12) Å

b = 8.2265 (14) Å

c = 9.9957 (17) Å

α = 114.093 (2)°

β = 104.033 (15)°

γ = 92.201 (13)°

V = 567.20 (16) Å3

Z = 2

Mo Kα radiation

μ = 2.79 mm−1

T = 100 K

0.39 × 0.04 × 0.01 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.409, T max = 0.972

7816 measured reflections

2798 independent reflections

2503 reflections with I > 2σ(I)

R int = 0.089

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.066

S = 0.96

2798 reflections

128 parameters

H-atom parameters constrained

Δρmax = 1.58 e Å−3

Δρmin = −1.35 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT-Plus (Bruker, 1999 ▶); data reduction: SAINT-Plus (Bruker, 1999 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812035611/im2367sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812035611/im2367Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812035611/im2367Isup3.cml

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

C10H12N3+·I−	Z = 2
Mr = 301.13	F(000) = 292
Triclinic, P1	Dx = 1.763 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8839 (12) Å	Cell parameters from 2049 reflections
b = 8.2265 (14) Å	θ = 2.3–25.1°
c = 9.9957 (17) Å	µ = 2.79 mm−1
α = 114.093 (2)°	T = 100 K
β = 104.033 (15)°	Rod, yellow
γ = 92.201 (13)°	0.39 × 0.04 × 0.01 mm
V = 567.20 (16) Å3

Bruker SMART CCD area-detector diffractometer	2798 independent reflections
Radiation source: Incoatec microsource	2503 reflections with I > 2σ(I)
Multilayer optics monochromator	Rint = 0.089
ω scans	θmax = 28.3°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.409, Tmax = 0.972	k = −10→10
7816 measured reflections	l = −13→13

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.066	H-atom parameters constrained
S = 0.96	w = 1/[σ2(Fo2) + (0.006P)2] where P = (Fo2 + 2Fc2)/3
2798 reflections	(Δ/σ)max = 0.002
128 parameters	Δρmax = 1.58 e Å−3
0 restraints	Δρmin = −1.35 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
N1	0.7209 (4)	0.1330 (4)	0.4718 (3)	0.0164 (7)
N2	0.7597 (4)	−0.0107 (4)	0.3708 (3)	0.0176 (7)
N3	0.6104 (4)	−0.0914 (4)	0.2612 (3)	0.0147 (7)
C1	0.4725 (5)	0.0022 (5)	0.2899 (4)	0.0140 (8)
C2	0.5465 (5)	0.1512 (5)	0.4296 (4)	0.0148 (8)
C3	0.4457 (5)	0.2804 (5)	0.4962 (4)	0.0187 (8)
H3	0.4955	0.3832	0.5906	0.022*
C4	0.2706 (5)	0.2495 (5)	0.4171 (4)	0.0211 (9)
H4	0.1965	0.3331	0.4589	0.025*
C5	0.1956 (5)	0.0978 (5)	0.2754 (4)	0.0199 (9)
H5	0.0733	0.0831	0.2252	0.024*
C6	0.2947 (5)	−0.0288 (5)	0.2084 (4)	0.0168 (8)
H6	0.2454	−0.1304	0.1131	0.020*
C7	0.6077 (5)	−0.2619 (5)	0.1295 (4)	0.0177 (8)
H7A	0.4846	−0.3094	0.0634	0.021*
H7B	0.6502	−0.3519	0.1665	0.021*
C8	0.7214 (5)	−0.2358 (5)	0.0381 (4)	0.0205 (9)
H8	0.7091	−0.1396	0.0089	0.025*
C9	0.8387 (5)	−0.3421 (6)	−0.0034 (5)	0.0271 (10)
H9A	0.8527	−0.4390	0.0250	0.033*
H9B	0.9091	−0.3218	−0.0615	0.033*
C10	0.8626 (5)	0.2617 (5)	0.6012 (4)	0.0220 (9)
H10A	0.9640	0.2009	0.6201	0.033*
H10B	0.8201	0.3103	0.6922	0.033*
H10C	0.8987	0.3604	0.5781	0.033*
I1	0.77374 (3)	0.33493 (3)	0.22631 (3)	0.01529 (8)

	U11	U22	U33	U12	U13	U23
N1	0.0169 (18)	0.0148 (17)	0.0179 (17)	0.0011 (13)	0.0009 (14)	0.0098 (14)
N2	0.0197 (19)	0.0169 (18)	0.0164 (17)	0.0031 (14)	0.0022 (14)	0.0092 (15)
N3	0.0154 (17)	0.0100 (16)	0.0167 (16)	0.0018 (12)	0.0015 (13)	0.0056 (14)
C1	0.019 (2)	0.0129 (19)	0.0162 (19)	0.0060 (15)	0.0081 (16)	0.0097 (16)
C2	0.014 (2)	0.0121 (19)	0.0166 (19)	−0.0022 (15)	−0.0004 (15)	0.0079 (16)
C3	0.027 (2)	0.015 (2)	0.0168 (19)	0.0045 (17)	0.0080 (17)	0.0081 (17)
C4	0.027 (2)	0.018 (2)	0.024 (2)	0.0103 (17)	0.0139 (18)	0.0103 (18)
C5	0.017 (2)	0.022 (2)	0.025 (2)	0.0064 (16)	0.0047 (17)	0.0136 (19)
C6	0.019 (2)	0.015 (2)	0.0153 (19)	0.0016 (16)	0.0012 (16)	0.0071 (16)
C7	0.019 (2)	0.013 (2)	0.019 (2)	0.0038 (15)	0.0043 (16)	0.0047 (17)
C8	0.026 (2)	0.014 (2)	0.017 (2)	−0.0011 (16)	0.0033 (17)	0.0052 (17)
C9	0.023 (2)	0.031 (3)	0.025 (2)	0.0036 (19)	0.0062 (18)	0.010 (2)
C10	0.018 (2)	0.022 (2)	0.019 (2)	−0.0017 (17)	−0.0013 (17)	0.0061 (18)
I1	0.01635 (15)	0.01309 (14)	0.01588 (14)	0.00263 (10)	0.00268 (10)	0.00672 (11)

N1—N2	1.309 (4)	C5—C6	1.375 (5)
N1—C2	1.370 (5)	C5—H5	0.9500
N1—C10	1.460 (4)	C6—H6	0.9500
N2—N3	1.322 (4)	C7—C8	1.492 (5)
N3—C1	1.376 (4)	C7—H7A	0.9900
N3—C7	1.476 (4)	C7—H7B	0.9900
C1—C2	1.394 (5)	C8—C9	1.321 (5)
C1—C6	1.394 (5)	C8—H8	0.9500
C2—C3	1.396 (5)	C9—H9A	0.9500
C3—C4	1.370 (5)	C9—H9B	0.9500
C3—H3	0.9500	C10—H10A	0.9800
C4—C5	1.417 (5)	C10—H10B	0.9800
C4—H4	0.9500	C10—H10C	0.9800
N2—N1—C2	112.4 (3)	C5—C6—C1	115.4 (3)
N2—N1—C10	119.4 (3)	C5—C6—H6	122.3
C2—N1—C10	127.7 (3)	C1—C6—H6	122.3
N1—N2—N3	105.9 (3)	N3—C7—C8	111.4 (3)
N2—N3—C1	111.9 (3)	N3—C7—H7A	109.3
N2—N3—C7	119.8 (3)	C8—C7—H7A	109.3
C1—N3—C7	128.3 (3)	N3—C7—H7B	109.3
N3—C1—C2	104.8 (3)	C8—C7—H7B	109.3
N3—C1—C6	132.4 (3)	H7A—C7—H7B	108.0
C2—C1—C6	122.8 (3)	C9—C8—C7	122.1 (4)
N1—C2—C1	105.0 (3)	C9—C8—H8	118.9
N1—C2—C3	133.4 (4)	C7—C8—H8	118.9
C1—C2—C3	121.6 (4)	C8—C9—H9A	120.0
C4—C3—C2	115.8 (4)	C8—C9—H9B	120.0
C4—C3—H3	122.1	H9A—C9—H9B	120.0
C2—C3—H3	122.1	N1—C10—H10A	109.5
C3—C4—C5	122.5 (4)	N1—C10—H10B	109.5
C3—C4—H4	118.7	H10A—C10—H10B	109.5
C5—C4—H4	118.7	N1—C10—H10C	109.5
C6—C5—C4	121.9 (4)	H10A—C10—H10C	109.5
C6—C5—H5	119.1	H10B—C10—H10C	109.5
C4—C5—H5	119.1