2-(3-Methoxy-phen-yl)butane-dinitrile.

In the title compound, C(11)H(10)N(2)O, the dicyano-ethyl-ene portion has an anti conformation. The crystal structure features non-classical C-H⋯N and C-H⋯O inter-actions.

Related literature

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

Experimental

Crystal data

C11H10N2O

M = 186.21

Monoclinic,

a = 5.5263 (8) Å

b = 16.105 (2) Å

c = 11.0332 (16) Å

β = 97.179 (2)°

V = 974.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.4 × 0.2 × 0.1 mm

Data collection

Bruker SMART area-detector diffractometer

Absorption correction: none

8042 measured reflections

2210 independent reflections

1963 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.128

S = 1.04

2210 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; 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: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809015232/ng2569sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015232/ng2569Isup2.hkl

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

C11H10N2O	F(000) = 392
Mr = 186.21	Dx = 1.270 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5752 reflections
a = 5.5263 (8) Å	θ = 2.3–27.4°
b = 16.105 (2) Å	µ = 0.08 mm−1
c = 11.0332 (16) Å	T = 298 K
β = 97.179 (2)°	Block, colorless
V = 974.3 (2) Å3	0.4 × 0.2 × 0.1 mm
Z = 4

Bruker SMART area-detector diffractometer	1963 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
graphite	θmax = 27.5°, θmin = 2.3°
φ and ω scans	h = −7→7
8042 measured reflections	k = −20→20
2210 independent reflections	l = −14→14

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0729P)2 + 0.1612P] where P = (Fo2 + 2Fc2)/3
2210 reflections	(Δ/σ)max = 0.001
128 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.21 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
C6	0.6739 (2)	0.85144 (7)	0.67253 (10)	0.0379 (3)
C7	0.5211 (2)	0.80066 (7)	0.73097 (11)	0.0406 (3)
H7	0.4177	0.8237	0.7822	0.049*
C5	0.8292 (3)	0.81733 (9)	0.59747 (12)	0.0518 (3)
H5	0.9321	0.8512	0.5588	0.062*
C2	0.5237 (2)	0.71565 (7)	0.71258 (11)	0.0439 (3)
C3	0.6789 (3)	0.68150 (8)	0.63618 (14)	0.0551 (4)
H3	0.6799	0.6245	0.6231	0.066*
C4	0.8306 (3)	0.73211 (9)	0.58018 (15)	0.0622 (4)
H4	0.9358	0.7090	0.5299	0.075*
C8	0.6709 (2)	0.94492 (7)	0.69077 (10)	0.0384 (3)
H8	0.7891	0.9698	0.6423	0.046*
C10	0.7385 (2)	0.97151 (7)	0.82538 (11)	0.0414 (3)
H10A	0.7311	1.0315	0.8311	0.050*
H10B	0.6209	0.9485	0.8744	0.050*
C9	0.4279 (2)	0.97888 (7)	0.64751 (11)	0.0435 (3)
O1	0.37911 (19)	0.66090 (5)	0.76429 (10)	0.0605 (3)
C1	0.2421 (3)	0.69035 (10)	0.85616 (15)	0.0638 (4)
H1A	0.3505	0.7141	0.9218	0.096*
H1B	0.1545	0.6450	0.8867	0.096*
H1C	0.1286	0.7318	0.8221	0.096*
N1	0.2393 (2)	1.00418 (8)	0.61421 (12)	0.0604 (3)
C11	0.9826 (2)	0.94328 (7)	0.87350 (10)	0.0415 (3)
N2	1.1722 (2)	0.92210 (8)	0.91331 (11)	0.0581 (3)

	U11	U22	U33	U12	U13	U23
C6	0.0380 (6)	0.0381 (6)	0.0376 (5)	−0.0021 (4)	0.0054 (4)	−0.0030 (4)
C7	0.0415 (6)	0.0363 (6)	0.0462 (6)	−0.0003 (4)	0.0139 (5)	−0.0042 (4)
C5	0.0540 (8)	0.0522 (7)	0.0537 (7)	−0.0070 (6)	0.0239 (6)	−0.0074 (5)
C2	0.0443 (6)	0.0368 (6)	0.0518 (6)	−0.0028 (5)	0.0112 (5)	−0.0029 (5)
C3	0.0617 (8)	0.0384 (6)	0.0679 (8)	0.0001 (5)	0.0188 (6)	−0.0143 (6)
C4	0.0668 (9)	0.0565 (8)	0.0696 (9)	−0.0002 (7)	0.0339 (7)	−0.0175 (7)
C8	0.0364 (6)	0.0373 (6)	0.0417 (6)	−0.0028 (4)	0.0053 (4)	0.0024 (4)
C10	0.0399 (6)	0.0366 (5)	0.0467 (6)	0.0036 (4)	0.0019 (5)	−0.0048 (4)
C9	0.0436 (7)	0.0397 (6)	0.0460 (6)	−0.0049 (5)	0.0007 (5)	0.0055 (5)
O1	0.0694 (7)	0.0352 (5)	0.0829 (7)	−0.0077 (4)	0.0339 (5)	−0.0025 (4)
C1	0.0727 (10)	0.0539 (8)	0.0708 (9)	−0.0093 (7)	0.0331 (8)	0.0033 (7)
N1	0.0479 (7)	0.0619 (7)	0.0679 (8)	0.0001 (5)	−0.0065 (5)	0.0126 (6)
C11	0.0429 (6)	0.0402 (6)	0.0413 (6)	0.0009 (5)	0.0050 (5)	−0.0025 (4)
N2	0.0469 (6)	0.0739 (8)	0.0525 (6)	0.0129 (5)	0.0023 (5)	−0.0037 (5)

C6—C5	1.3791 (16)	C8—C9	1.4730 (16)
C6—C7	1.3903 (15)	C8—C10	1.5460 (16)
C6—C8	1.5193 (15)	C8—H8	0.9800
C7—C2	1.3843 (16)	C10—C11	1.4593 (16)
C7—H7	0.9300	C10—H10A	0.9700
C5—C4	1.386 (2)	C10—H10B	0.9700
C5—H5	0.9300	C9—N1	1.1365 (16)
C2—O1	1.3623 (15)	O1—C1	1.4205 (17)
C2—C3	1.3890 (17)	C1—H1A	0.9600
C3—C4	1.371 (2)	C1—H1B	0.9600
C3—H3	0.9300	C1—H1C	0.9600
C4—H4	0.9300	C11—N2	1.1368 (16)
C5—C6—C7	120.25 (11)	C6—C8—C10	113.36 (9)
C5—C6—C8	119.48 (10)	C9—C8—H8	108.3
C7—C6—C8	120.28 (9)	C6—C8—H8	108.3
C2—C7—C6	119.71 (10)	C10—C8—H8	108.3
C2—C7—H7	120.1	C11—C10—C8	111.38 (9)
C6—C7—H7	120.1	C11—C10—H10A	109.4
C6—C5—C4	119.46 (12)	C8—C10—H10A	109.4
C6—C5—H5	120.3	C11—C10—H10B	109.4
C4—C5—H5	120.3	C8—C10—H10B	109.4
O1—C2—C7	124.16 (11)	H10A—C10—H10B	108.0
O1—C2—C3	115.90 (11)	N1—C9—C8	179.20 (13)
C7—C2—C3	119.94 (11)	C2—O1—C1	118.40 (10)
C4—C3—C2	119.79 (11)	O1—C1—H1A	109.5
C4—C3—H3	120.1	O1—C1—H1B	109.5
C2—C3—H3	120.1	H1A—C1—H1B	109.5
C3—C4—C5	120.84 (12)	O1—C1—H1C	109.5
C3—C4—H4	119.6	H1A—C1—H1C	109.5
C5—C4—H4	119.6	H1B—C1—H1C	109.5
C9—C8—C6	110.45 (9)	N2—C11—C10	178.53 (13)
C9—C8—C10	108.02 (9)
C5—C6—C7—C2	−0.64 (18)	C6—C5—C4—C3	0.3 (2)
C8—C6—C7—C2	179.32 (11)	C5—C6—C8—C9	118.72 (12)
C7—C6—C5—C4	0.4 (2)	C7—C6—C8—C9	−61.25 (14)
C8—C6—C5—C4	−179.55 (13)	C5—C6—C8—C10	−119.90 (12)
C6—C7—C2—O1	−179.11 (11)	C7—C6—C8—C10	60.14 (14)
C6—C7—C2—C3	0.13 (19)	C9—C8—C10—C11	−177.45 (10)
O1—C2—C3—C4	179.91 (14)	C6—C8—C10—C11	59.81 (13)
C7—C2—C3—C4	0.6 (2)	C7—C2—O1—C1	−9.4 (2)
C2—C3—C4—C5	−0.8 (2)	C3—C2—O1—C1	171.30 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···N1i	0.98	2.61	3.4864 (17)	150
C10—H10A···O1ii	0.97	2.38	3.2470 (15)	149
C10—H10B···N2iii	0.97	2.60	3.4823 (18)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯N1i	0.98	2.61	3.4864 (17)	150
C10—H10A⋯O1ii	0.97	2.38	3.2470 (15)	149
C10—H10B⋯N2iii	0.97	2.60	3.4823 (18)	151

Symmetry codes: (i) ; (ii) ; (iii) .