2,6-Diazido-toluene.

The structure of the title compound, C(7)H(6)N(6), consists of almost planar mol-ecules with C-N distances of 1.429 (2) and 1.428 (2) Å. The H atoms of the methyl group are disordered over two sites with occupancy factors of 0.69 and 0.31. The azide groups show typical geometry for covalently bound azides.

Related literature

The preparation of the title compound by a slightly different procedure was reported by Chapyshev & Tomioka (2003 ▶). For the comparable compound, 2-azido­benzyl ­bromide, see: Klapötke et al. (2003 ▶).

Experimental

Crystal data

C7H6N6

M = 174.16

Orthorhombic,

a = 12.298 (5) Å

b = 25.896 (5) Å

c = 5.085 (5) Å

V = 1619.4 (18) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 200 (2) K

0.29 × 0.14 × 0.13 mm

Data collection

Oxford Xcalibur3 CCD area-detector diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.899, T max = 0.990

5871 measured reflections

1578 independent reflections

956 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.061

S = 0.94

1578 reflections

143 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.10 e Å−3

Δρmin = −0.12 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: DIAMOND (Brandenburg, 1996 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680706744X/fj2092sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680706744X/fj2092Isup2.hkl

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

C7H6N6	F000 = 720
Mr = 174.16	Dx = 1.429 (1) Mg m−3
Orthorhombic, Pccn	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 1382 reflections
a = 12.298 (5) Å	θ = 3.9–30.0º
b = 25.896 (5) Å	µ = 0.10 mm−1
c = 5.085 (5) Å	T = 200 (2) K
V = 1619.4 (18) Å3	Needle, colorless
Z = 8	0.29 × 0.14 × 0.13 mm

Oxford Xcalibur3 CCD area-detector diffractometer	1578 independent reflections
Radiation source: fine-focus sealed tube	956 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.040
Detector resolution: 15.9809 pixels mm-1	θmax = 26.0º
T = 200(2) K	θmin = 4.3º
ω scans	h = −15→9
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2007)	k = −19→31
Tmin = 0.899, Tmax = 0.990	l = −5→6
5871 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)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.061	w = 1/[σ2(Fo2) + (0.0396P)2] where P = (Fo2 + 2Fc2)/3
S = 0.94	(Δ/σ)max < 0.001
1578 reflections	Δρmax = 0.11 e Å−3
143 parameters	Δρmin = −0.11 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Refinement. Aromatic H atoms were placed in idealized positions and allowed to ride on their respective parent atoms, with C–H = 0.95 (CaromH) and with Uiso(H) = kUeq(carrier atom), where k = 1.2 for CH. The H atoms attached to methyl C7 are disordered over two sites. These were freely refined; the occupancy of the major disorder component is 0.69 (5). The highest peak and deepest hole in the final difference map were located 0.93 Å from atom H7B and 0.32 Å from atom H7A, respectively.

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.45618 (11)	0.14719 (5)	0.0665 (3)	0.0348 (4)
C2	0.45326 (12)	0.10499 (5)	−0.1031 (3)	0.0353 (4)
C3	0.53072 (12)	0.06637 (6)	−0.0938 (3)	0.0415 (4)
H3	0.5271	0.0383	−0.2136	0.050*
C4	0.61302 (13)	0.06857 (6)	0.0888 (3)	0.0426 (4)
H4	0.6662	0.0420	0.0957	0.051*
C5	0.61819 (12)	0.10957 (5)	0.2622 (3)	0.0405 (4)
H5	0.6745	0.1111	0.3899	0.049*
C6	0.54110 (12)	0.14841 (5)	0.2495 (3)	0.0353 (4)
C7	0.37338 (17)	0.18935 (8)	0.0524 (5)	0.0462 (4)
H7A	0.297 (2)	0.1729 (9)	0.075 (5)	0.042 (10)*	0.69 (5)
H7B	0.385 (3)	0.2132 (11)	0.190 (8)	0.073 (11)*	0.69 (5)
H7C	0.381 (3)	0.2054 (10)	−0.129 (7)	0.060 (11)*	0.69 (5)
H7D	0.323 (4)	0.1895 (16)	−0.102 (10)	0.010 (16)*	0.31 (5)
H7E	0.334 (4)	0.193 (2)	0.231 (14)	0.04 (2)*	0.31 (5)
H7F	0.410 (4)	0.2239 (18)	0.031 (10)	0.015 (18)*	0.31 (5)
N1	0.36418 (10)	0.10504 (5)	−0.2837 (2)	0.0440 (4)
N2	0.35797 (10)	0.06789 (5)	−0.4371 (3)	0.0419 (3)
N3	0.34235 (11)	0.03628 (5)	−0.5865 (3)	0.0564 (4)
N4	0.54156 (10)	0.19271 (4)	0.4164 (3)	0.0440 (3)
N5	0.61378 (11)	0.19404 (4)	0.5897 (3)	0.0409 (3)
N6	0.67279 (12)	0.19998 (5)	0.7553 (3)	0.0528 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0329 (8)	0.0333 (8)	0.0382 (9)	−0.0034 (8)	0.0065 (8)	0.0026 (8)
C2	0.0346 (9)	0.0381 (8)	0.0332 (9)	−0.0052 (8)	0.0037 (8)	0.0030 (8)
C3	0.0440 (9)	0.0367 (8)	0.0436 (10)	0.0011 (9)	0.0053 (9)	−0.0017 (8)
C4	0.0415 (9)	0.0384 (8)	0.0480 (10)	0.0065 (9)	0.0043 (10)	0.0052 (9)
C5	0.0379 (9)	0.0444 (9)	0.0393 (9)	−0.0016 (9)	−0.0016 (9)	0.0050 (8)
C6	0.0367 (9)	0.0352 (8)	0.0340 (8)	−0.0039 (8)	0.0038 (8)	0.0013 (8)
C7	0.0428 (11)	0.0422 (10)	0.0537 (13)	0.0029 (11)	−0.0036 (12)	−0.0064 (12)
N1	0.0455 (8)	0.0406 (7)	0.0460 (8)	−0.0019 (7)	−0.0033 (7)	−0.0088 (7)
N2	0.0408 (8)	0.0462 (8)	0.0387 (8)	−0.0031 (8)	−0.0005 (7)	0.0000 (8)
N3	0.0611 (9)	0.0572 (9)	0.0510 (9)	−0.0003 (8)	−0.0051 (8)	−0.0148 (8)
N4	0.0455 (8)	0.0477 (8)	0.0388 (8)	−0.0006 (7)	−0.0065 (8)	−0.0063 (7)
N5	0.0455 (8)	0.0416 (8)	0.0357 (8)	−0.0052 (7)	0.0065 (8)	0.0007 (7)
N6	0.0545 (8)	0.0650 (10)	0.0389 (9)	−0.0080 (8)	−0.0047 (8)	−0.0028 (7)

C1—C2	1.393 (2)	C6—N4	1.4270 (19)
C1—C6	1.399 (2)	C7—H7A	1.04 (3)
C1—C7	1.495 (2)	C7—H7B	0.94 (3)
C2—C3	1.382 (2)	C7—H7C	1.02 (3)
C2—N1	1.4294 (19)	C7—H7D	1.00 (5)
C3—C4	1.375 (2)	C7—H7E	1.04 (7)
C3—H3	0.9500	C7—H7F	1.01 (5)
C4—C5	1.382 (2)	N1—N2	1.2410 (17)
C4—H4	0.9500	N2—N3	1.1331 (17)
C5—C6	1.3836 (19)	N4—N5	1.2518 (19)
C5—H5	0.9500	N5—N6	1.1222 (17)
C2—C1—C6	116.67 (13)	H7A—C7—H7C	111 (2)
C2—C1—C7	121.72 (16)	H7B—C7—H7C	113 (2)
C6—C1—C7	121.60 (15)	C1—C7—H7D	118 (2)
C3—C2—C1	121.93 (15)	H7A—C7—H7D	62 (2)
C3—C2—N1	123.42 (13)	H7B—C7—H7D	132 (3)
C1—C2—N1	114.65 (14)	H7C—C7—H7D	49 (2)
C4—C3—C2	120.03 (15)	C1—C7—H7E	110 (2)
C4—C3—H3	120.0	H7A—C7—H7E	61 (3)
C2—C3—H3	120.0	H7B—C7—H7E	50 (3)
C3—C4—C5	119.80 (15)	H7C—C7—H7E	143 (3)
C3—C4—H4	120.1	H7D—C7—H7E	113 (3)
C5—C4—H4	120.1	C1—C7—H7F	110 (2)
C4—C5—C6	119.80 (14)	H7A—C7—H7F	141 (2)
C4—C5—H5	120.1	H7B—C7—H7F	55 (2)
C6—C5—H5	120.1	H7C—C7—H7F	60 (2)
C5—C6—C1	121.76 (13)	H7D—C7—H7F	101 (3)
C5—C6—N4	123.63 (14)	H7E—C7—H7F	103 (3)
C1—C6—N4	114.61 (13)	N2—N1—C2	116.77 (13)
C1—C7—H7A	108.3 (11)	N3—N2—N1	172.70 (16)
C1—C7—H7B	109.8 (17)	N5—N4—C6	116.34 (13)
H7A—C7—H7B	109 (3)	N6—N5—N4	172.29 (15)
C1—C7—H7C	106.0 (15)
C6—C1—C2—C3	−0.6 (2)	C4—C5—C6—N4	−178.50 (14)
C7—C1—C2—C3	178.86 (16)	C2—C1—C6—C5	−0.2 (2)
C6—C1—C2—N1	179.09 (12)	C7—C1—C6—C5	−179.69 (16)
C7—C1—C2—N1	−1.5 (2)	C2—C1—C6—N4	179.16 (13)
C1—C2—C3—C4	0.8 (2)	C7—C1—C6—N4	−0.3 (2)
N1—C2—C3—C4	−178.84 (13)	C3—C2—N1—N2	0.2 (2)
C2—C3—C4—C5	−0.2 (2)	C1—C2—N1—N2	−179.43 (13)
C3—C4—C5—C6	−0.6 (2)	C5—C6—N4—N5	−3.5 (2)
C4—C5—C6—C1	0.8 (2)	C1—C6—N4—N5	177.14 (13)