2-(2-Methoxy-phen-yl)butane-dinitrile.

In the title compound, C(11)H(10)N(2)O, the butane-dinitrile unit adopts a synclinal conformation. The crystal packing is stabilized by weak inter-molecular C-H⋯N hydrogen bonding.

Related literature

The title compound is an important inter­mediate in drugs synthesis, see: Obniska et al. (2005 ▶). For the synthesis, see: Johnson et al. (1962 ▶).

Experimental

Crystal data

C11H10N2O

M = 186.21

Monoclinic,

a = 12.393 (9) Å

b = 5.405 (4) Å

c = 15.216 (10) Å

β = 102.947 (8)°

V = 993.3 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.37 × 0.25 × 0.14 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.970, T max = 0.985

7820 measured reflections

2292 independent reflections

1549 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.116

S = 1.04

2292 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810013462/xu2746sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013462/xu2746Isup2.hkl

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

C11H10N2O	F(000) = 392
Mr = 186.21	Dx = 1.245 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2518 reflections
a = 12.393 (9) Å	θ = 2.8–26.1°
b = 5.405 (4) Å	µ = 0.08 mm−1
c = 15.216 (10) Å	T = 298 K
β = 102.947 (8)°	Block, colorless
V = 993.3 (12) Å3	0.37 × 0.25 × 0.14 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	2292 independent reflections
Radiation source: fine-focus sealed tube	1549 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 27.7°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→16
Tmin = 0.970, Tmax = 0.985	k = −6→6
7820 measured reflections	l = −18→19

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.051P)2 + 0.1131P] where P = (Fo2 + 2Fc2)/3
2292 reflections	(Δ/σ)max < 0.001
128 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.14 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
C1	0.34900 (15)	1.2727 (3)	0.69677 (11)	0.0644 (5)
H1A	0.3731	1.1717	0.6529	0.097*
H1B	0.4106	1.3657	0.7303	0.097*
H1C	0.2924	1.3843	0.6667	0.097*
N1	0.45207 (12)	0.7505 (3)	1.07568 (10)	0.0728 (4)
O1	0.30584 (9)	1.11902 (19)	0.75662 (6)	0.0581 (3)
C2	0.22452 (11)	0.9545 (3)	0.72065 (9)	0.0461 (3)
N2	0.22425 (13)	1.2438 (2)	0.95010 (9)	0.0660 (4)
C3	0.17425 (13)	0.9391 (3)	0.63011 (10)	0.0585 (4)
H3	0.1945	1.0466	0.5889	0.070*
C4	0.09351 (14)	0.7621 (3)	0.60142 (11)	0.0642 (5)
H4	0.0591	0.7523	0.5406	0.077*
C5	0.06344 (13)	0.6016 (3)	0.66096 (11)	0.0605 (4)
H5	0.0102	0.4810	0.6406	0.073*
C6	0.11252 (11)	0.6197 (3)	0.75120 (10)	0.0500 (4)
H6	0.0913	0.5117	0.7919	0.060*
C7	0.19287 (11)	0.7958 (2)	0.78245 (8)	0.0409 (3)
C8	0.24600 (11)	0.8102 (2)	0.88203 (9)	0.0422 (3)
H8	0.2064	0.6939	0.9129	0.051*
C9	0.36818 (12)	0.7315 (3)	0.90375 (10)	0.0518 (4)
H9A	0.3741	0.5645	0.8819	0.062*
H9B	0.4096	0.8402	0.8727	0.062*
C10	0.41624 (12)	0.7404 (3)	1.00039 (11)	0.0547 (4)
C11	0.23445 (11)	1.0568 (3)	0.91933 (9)	0.0457 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0803 (11)	0.0570 (10)	0.0640 (10)	−0.0141 (8)	0.0332 (9)	0.0021 (8)
N1	0.0724 (10)	0.0769 (10)	0.0604 (9)	0.0051 (7)	−0.0034 (7)	0.0056 (7)
O1	0.0726 (7)	0.0561 (6)	0.0471 (6)	−0.0181 (5)	0.0167 (5)	0.0032 (5)
C2	0.0515 (8)	0.0429 (8)	0.0447 (7)	0.0002 (6)	0.0129 (6)	−0.0007 (6)
N2	0.0978 (11)	0.0466 (8)	0.0543 (8)	0.0086 (7)	0.0183 (7)	−0.0036 (6)
C3	0.0678 (10)	0.0649 (10)	0.0435 (8)	−0.0002 (8)	0.0138 (7)	0.0049 (7)
C4	0.0639 (10)	0.0787 (12)	0.0451 (8)	0.0010 (9)	0.0018 (7)	−0.0066 (8)
C5	0.0527 (9)	0.0664 (10)	0.0593 (9)	−0.0081 (7)	0.0057 (7)	−0.0090 (8)
C6	0.0500 (8)	0.0463 (8)	0.0543 (9)	−0.0010 (6)	0.0131 (6)	0.0000 (6)
C7	0.0450 (7)	0.0372 (7)	0.0413 (7)	0.0039 (5)	0.0112 (6)	0.0004 (5)
C8	0.0507 (8)	0.0357 (7)	0.0413 (7)	0.0008 (6)	0.0124 (6)	0.0033 (5)
C9	0.0544 (8)	0.0499 (9)	0.0495 (8)	0.0090 (6)	0.0081 (6)	0.0022 (6)
C10	0.0530 (8)	0.0493 (9)	0.0579 (9)	0.0065 (7)	0.0041 (7)	0.0054 (7)
C11	0.0555 (8)	0.0434 (8)	0.0382 (7)	0.0030 (6)	0.0102 (6)	0.0039 (6)

C1—O1	1.4225 (18)	C4—H4	0.9300
C1—H1A	0.9600	C5—C6	1.375 (2)
C1—H1B	0.9600	C5—H5	0.9300
C1—H1C	0.9600	C6—C7	1.383 (2)
N1—C10	1.133 (2)	C6—H6	0.9300
O1—C2	1.3632 (17)	C7—C8	1.513 (2)
C2—C3	1.381 (2)	C8—C11	1.468 (2)
C2—C7	1.3928 (19)	C8—C9	1.536 (2)
N2—C11	1.1327 (18)	C8—H8	0.9800
C3—C4	1.382 (2)	C9—C10	1.458 (2)
C3—H3	0.9300	C9—H9A	0.9700
C4—C5	1.365 (2)	C9—H9B	0.9700
O1—C1—H1A	109.5	C5—C6—H6	119.5
O1—C1—H1B	109.5	C7—C6—H6	119.5
H1A—C1—H1B	109.5	C6—C7—C2	118.83 (13)
O1—C1—H1C	109.5	C6—C7—C8	119.89 (12)
H1A—C1—H1C	109.5	C2—C7—C8	121.28 (12)
H1B—C1—H1C	109.5	C11—C8—C7	112.07 (10)
C2—O1—C1	118.29 (12)	C11—C8—C9	110.19 (11)
O1—C2—C3	124.58 (13)	C7—C8—C9	112.84 (11)
O1—C2—C7	115.18 (12)	C11—C8—H8	107.1
C3—C2—C7	120.24 (13)	C7—C8—H8	107.1
C2—C3—C4	119.32 (14)	C9—C8—H8	107.1
C2—C3—H3	120.3	C10—C9—C8	111.60 (12)
C4—C3—H3	120.3	C10—C9—H9A	109.3
C5—C4—C3	121.07 (15)	C8—C9—H9A	109.3
C5—C4—H4	119.5	C10—C9—H9B	109.3
C3—C4—H4	119.5	C8—C9—H9B	109.3
C4—C5—C6	119.48 (15)	H9A—C9—H9B	108.0
C4—C5—H5	120.3	N1—C10—C9	178.67 (17)
C6—C5—H5	120.3	N2—C11—C8	177.91 (15)
C5—C6—C7	121.04 (14)
C1—O1—C2—C3	−5.4 (2)	C3—C2—C7—C6	1.5 (2)
C1—O1—C2—C7	174.73 (13)	O1—C2—C7—C8	0.32 (18)
O1—C2—C3—C4	179.19 (15)	C3—C2—C7—C8	−179.53 (12)
C7—C2—C3—C4	−1.0 (2)	C6—C7—C8—C11	−123.69 (14)
C2—C3—C4—C5	−0.5 (2)	C2—C7—C8—C11	57.39 (17)
C3—C4—C5—C6	1.4 (3)	C6—C7—C8—C9	111.21 (15)
C4—C5—C6—C7	−0.8 (2)	C2—C7—C8—C9	−67.71 (16)
C5—C6—C7—C2	−0.6 (2)	C11—C8—C9—C10	55.55 (15)
C5—C6—C7—C8	−179.58 (13)	C7—C8—C9—C10	−178.33 (11)
O1—C2—C7—C6	−178.61 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N2i	0.93	2.50	3.404 (3)	165
C8—H8···N2ii	0.98	2.50	3.262 (3)	135

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯N2i	0.93	2.50	3.404 (3)	165
C8—H8⋯N2ii	0.98	2.50	3.262 (3)	135

Symmetry codes: (i) ; (ii) .