2,5-Di-meth-oxy-benzo-nitrile.

In the title mol-ecule, C9H9NO2, the non-H atoms are essentially coplanar with a maximum deviation of 0.027 (2) Å for the C atom of one of the methyl groups. In the crystal, the mol-ecules are arranged into centrosymmetric pairs via pairs of C-H⋯O and C-H⋯N inter-actions whereas π-π stacking inter-actions between the benzene rings [centroid-centroid distance 3.91001 (15) Å] organize them into polymeric strands propagating along the a-axis direction. There is a step of 0.644 (2) Å between the two planar parts of the centrosymmetric pair. In neighboring strands related by the n-glide operation, the aromatic rings are tilted by 29.08 (2)°.

Related literature

For the use of the title compound as a key reagent in the synthesis of pharmaceutically active heterocycles, see: Bergeron et al. (2006 ▶); Delgado et al. (1987 ▶). For another method of preparation of the title compound, see: Ushijima et al. (2012 ▶). For the crystal structures of aromatic nitriles, see: Buschmann et al. (1995 ▶); Zabinski et al. (2007 ▶); Zanotti et al. (1980 ▶).

Experimental

Crystal data

C9H9NO2

M = 163.17

Monoclinic,

a = 3.91001 (15) Å

b = 11.3347 (4) Å

c = 17.8432 (6) Å

β = 93.400 (3)°

V = 789.40 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.60 × 0.25 × 0.23 mm

Data collection

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013 ▶) T min = 0.899, T max = 1.000

3225 measured reflections

1785 independent reflections

1374 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.116

S = 1.06

1785 reflections

111 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CrysAlis PRO (Agilent, 2013 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) within OLEX2 (Dolomanov et al., 2009 ▶); molecular graphics: PLATON (Spek, 2009 ▶); Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813031309/gk2594sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813031309/gk2594Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813031309/gk2594Isup3.cml

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

C9H9NO2	Dx = 1.373 Mg m−3
Mr = 163.17	Melting point = 360–361 K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.7107 Å
a = 3.91001 (15) Å	Cell parameters from 1290 reflections
b = 11.3347 (4) Å	θ = 3.6–32.0°
c = 17.8432 (6) Å	µ = 0.10 mm−1
β = 93.400 (3)°	T = 100 K
V = 789.40 (5) Å3	Block, colourless
Z = 4	0.60 × 0.25 × 0.23 mm
F(000) = 344

Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer	1785 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1374 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.026
Detector resolution: 10.4127 pixels mm-1	θmax = 27.5°, θmin = 3.6°
ω scans	h = −5→4
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −9→14
Tmin = 0.899, Tmax = 1.000	l = −21→23
3225 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044	H-atom parameters constrained
wR(F2) = 0.116	w = 1/[σ2(Fo2) + (0.048P)2 + 0.110P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
1785 reflections	Δρmax = 0.21 e Å−3
111 parameters	Δρmin = −0.24 e Å−3
0 restraints

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.

	x	y	z	Uiso*/Ueq
C1	1.1608 (4)	0.84580 (13)	0.32618 (8)	0.0170 (3)
C2	1.1137 (4)	0.96337 (13)	0.34798 (7)	0.0170 (3)
C3	0.9434 (4)	1.03957 (13)	0.29791 (8)	0.0178 (3)
C4	0.8238 (4)	1.00071 (13)	0.22693 (8)	0.0180 (3)
C5	0.8723 (4)	0.88435 (13)	0.20555 (8)	0.0166 (3)
C6	1.0425 (4)	0.80699 (13)	0.25538 (7)	0.0178 (3)
C7	1.3310 (4)	0.76401 (14)	0.37753 (8)	0.0193 (3)
C8	1.1889 (4)	1.11088 (14)	0.44323 (8)	0.0214 (4)
C9	0.5943 (4)	0.91476 (14)	0.08362 (8)	0.0227 (4)
H3	0.9077	1.1192	0.3120	0.021*
H4	0.7086	1.0541	0.1930	0.022*
H6	1.0782	0.7274	0.2410	0.021*
H8A	1.2963	1.1668	0.4099	0.032*
H8B	1.2895	1.1202	0.4945	0.032*
H8C	0.9421	1.1264	0.4425	0.032*
H9A	0.5317	0.8708	0.0375	0.034*
H9B	0.7498	0.9793	0.0723	0.034*
H9C	0.3872	0.9472	0.1041	0.034*
N1	1.4646 (4)	0.69750 (12)	0.41812 (7)	0.0264 (3)
O1	1.2456 (3)	0.99244 (9)	0.41788 (5)	0.0202 (3)
O2	0.7618 (3)	0.83694 (9)	0.13775 (5)	0.0219 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0161 (7)	0.0162 (8)	0.0189 (7)	−0.0002 (6)	0.0038 (5)	0.0027 (6)
C2	0.0161 (8)	0.0185 (8)	0.0165 (7)	−0.0017 (6)	0.0025 (5)	0.0012 (6)
C3	0.0184 (8)	0.0147 (7)	0.0204 (7)	0.0000 (6)	0.0026 (6)	−0.0003 (6)
C4	0.0178 (8)	0.0170 (7)	0.0194 (7)	0.0008 (6)	0.0024 (6)	0.0039 (6)
C5	0.0157 (7)	0.0176 (8)	0.0165 (7)	−0.0028 (6)	0.0020 (5)	0.0008 (6)
C6	0.0169 (8)	0.0164 (7)	0.0206 (7)	−0.0007 (6)	0.0041 (6)	−0.0001 (6)
C7	0.0210 (8)	0.0174 (8)	0.0196 (7)	−0.0005 (7)	0.0030 (6)	−0.0018 (6)
C8	0.0260 (9)	0.0184 (8)	0.0196 (7)	0.0012 (7)	−0.0007 (6)	−0.0027 (6)
C9	0.0256 (9)	0.0229 (8)	0.0189 (7)	−0.0011 (7)	−0.0029 (6)	0.0031 (6)
N1	0.0334 (9)	0.0212 (7)	0.0243 (7)	0.0046 (6)	−0.0004 (6)	0.0003 (6)
O1	0.0258 (6)	0.0172 (6)	0.0171 (5)	0.0027 (5)	−0.0029 (4)	−0.0009 (4)
O2	0.0281 (6)	0.0196 (6)	0.0174 (5)	0.0000 (5)	−0.0033 (4)	0.0002 (4)

C2—C1	1.404 (2)	C8—H8C	0.9800
C2—C3	1.384 (2)	C8—H8B	0.9800
C3—C4	1.395 (2)	C8—H8A	0.9800
C3—H3	0.9500	C9—H9C	0.9800
C4—H4	0.9500	C9—H9B	0.9800
C5—C4	1.389 (2)	C9—H9A	0.9800
C5—C6	1.390 (2)	O1—C8	1.4381 (18)
C6—C1	1.391 (2)	O1—C2	1.3616 (17)
C6—H6	0.9500	O2—C9	1.4370 (18)
C7—N1	1.1492 (19)	O2—C5	1.3700 (17)
C7—C1	1.439 (2)
C1—C6—H6	119.9	H8A—C8—H8B	109.5
C2—C1—C7	119.92 (13)	H8B—C8—H8C	109.5
C2—C3—C4	120.75 (14)	H9A—C9—H9C	109.5
C2—C3—H3	119.6	H9A—C9—H9B	109.5
C2—O1—C8	117.18 (11)	H9B—C9—H9C	109.5
C3—C4—H4	119.8	N1—C7—C1	179.12 (16)
C3—C2—C1	118.65 (13)	O1—C8—H8C	109.5
C4—C3—H3	119.6	O1—C8—H8B	109.5
C4—C5—C6	119.42 (13)	O1—C8—H8A	109.5
C5—C4—H4	119.8	O1—C2—C1	115.77 (13)
C5—C4—C3	120.35 (14)	O1—C2—C3	125.57 (14)
C5—C6—C1	120.16 (14)	O2—C9—H9C	109.5
C5—C6—H6	119.9	O2—C9—H9B	109.5
C5—O2—C9	117.39 (11)	O2—C9—H9A	109.5
C6—C1—C7	119.42 (13)	O2—C5—C4	125.03 (13)
C6—C1—C2	120.67 (14)	O2—C5—C6	115.55 (13)
H8A—C8—H8C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···O1i	0.98	2.65	3.428 (2)	136
C8—H8B···N1i	0.98	2.73	3.504 (2)	136
C9—H9B···N1ii	0.98	2.71	3.640 (2)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8B⋯O1i	0.98	2.65	3.428 (2)	136
C8—H8B⋯N1i	0.98	2.73	3.504 (2)	136
C9—H9B⋯N1ii	0.98	2.71	3.640 (2)	158

Symmetry codes: (i) ; (ii) .