2-[4-(Benz-yloxy)benzyl-idene]malononitrile.

In the title mol-ecule, C(17)H(12)N(2)O, the dihedral angle between the two benzene rings is 84.98 (10)°. The dicyano-ethyl-ene group is coplanar with the benzene ring to which it is bonded. No classic hydrogen bonds were found in the crystal.

Related literature

For background information and the synthetic procedure for the title compound, see: Kharas et al. (2007 ▶). For a related crystal structure, see: Zhu et al. (2007 ▶).

Experimental

Crystal data

C17H12N2O

M = 260.29

Triclinic,

a = 6.8470 (14) Å

b = 9.6270 (19) Å

c = 10.544 (2) Å

α = 100.66 (3)°

β = 91.65 (3)°

γ = 94.26 (3)°

V = 680.5 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.976, T max = 0.992

2722 measured reflections

2496 independent reflections

1664 reflections with I > 2σ(I)

R int = 0.022

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.176

S = 1.00

2496 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.18 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812020053/pv2535sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812020053/pv2535Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812020053/pv2535Isup3.cml

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

C17H12N2O	Z = 2
Mr = 260.29	F(000) = 272
Triclinic, P1	Dx = 1.270 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8470 (14) Å	Cell parameters from 25 reflections
b = 9.6270 (19) Å	θ = 9–13°
c = 10.544 (2) Å	µ = 0.08 mm−1
α = 100.66 (3)°	T = 293 K
β = 91.65 (3)°	Block, yellow
γ = 94.26 (3)°	0.30 × 0.20 × 0.10 mm
V = 680.5 (2) Å3

Enraf–Nonius CAD-4 diffractometer	1664 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
Graphite monochromator	θmax = 25.4°, θmin = 2.0°
ω/2θ scans	h = 0→8
Absorption correction: ψ scan (North et al., 1968)	k = −11→11
Tmin = 0.976, Tmax = 0.992	l = −12→12
2722 measured reflections	3 standard reflections every 200 reflections
2496 independent reflections	intensity decay: 1%

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.176	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.1P)2 + 0.110P] where P = (Fo2 + 2Fc2)/3
2496 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.18 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
O	0.2390 (3)	0.75384 (16)	0.34116 (15)	0.0569 (5)
N1	0.2812 (4)	1.3682 (3)	0.0440 (2)	0.0787 (8)
C1	0.0380 (4)	0.6905 (3)	0.5996 (3)	0.0660 (7)
H1A	−0.0703	0.7323	0.5729	0.079*
N2	0.2608 (4)	1.1632 (3)	−0.3621 (2)	0.0701 (7)
C2	0.0139 (6)	0.5918 (3)	0.6777 (3)	0.0797 (9)
H2A	−0.1106	0.5677	0.7040	0.096*
C3	0.1676 (7)	0.5300 (3)	0.7164 (3)	0.0851 (10)
H3A	0.1490	0.4633	0.7694	0.102*
C4	0.3527 (7)	0.5639 (4)	0.6788 (3)	0.0929 (11)
H4A	0.4589	0.5201	0.7058	0.111*
C5	0.3809 (5)	0.6648 (3)	0.5994 (3)	0.0763 (9)
H5A	0.5057	0.6885	0.5735	0.092*
C6	0.2224 (4)	0.7285 (2)	0.5601 (2)	0.0538 (6)
C7	0.2449 (4)	0.8328 (3)	0.4716 (2)	0.0596 (7)
H7A	0.1395	0.8955	0.4823	0.072*
H7B	0.3686	0.8899	0.4911	0.072*
C8	0.2438 (3)	0.8250 (2)	0.2424 (2)	0.0459 (6)
C9	0.2554 (4)	0.9733 (2)	0.2554 (2)	0.0502 (6)
H9A	0.2617	1.0303	0.3371	0.060*
C10	0.2575 (4)	1.0339 (2)	0.1472 (2)	0.0503 (6)
H10A	0.2657	1.1321	0.1569	0.060*
C11	0.2476 (3)	0.9510 (2)	0.0223 (2)	0.0453 (6)
C12	0.2362 (4)	0.8023 (2)	0.0131 (2)	0.0518 (6)
H12A	0.2296	0.7444	−0.0682	0.062*
C13	0.2346 (4)	0.7412 (2)	0.1198 (2)	0.0519 (6)
H13A	0.2273	0.6430	0.1104	0.062*
C14	0.2497 (3)	1.0026 (2)	−0.0972 (2)	0.0486 (6)
H14A	0.2429	0.9312	−0.1703	0.058*
C15	0.2598 (3)	1.1353 (3)	−0.1240 (2)	0.0497 (6)
C16	0.2724 (4)	1.2637 (3)	−0.0292 (2)	0.0559 (6)
C17	0.2608 (4)	1.1526 (3)	−0.2562 (3)	0.0538 (6)

	U11	U22	U33	U12	U13	U23
O	0.0747 (12)	0.0428 (9)	0.0535 (10)	0.0013 (8)	0.0064 (8)	0.0105 (7)
N1	0.103 (2)	0.0531 (14)	0.0792 (16)	0.0068 (13)	0.0117 (14)	0.0093 (13)
C1	0.0692 (19)	0.0665 (17)	0.0622 (16)	0.0038 (14)	0.0117 (14)	0.0110 (13)
N2	0.0831 (18)	0.0672 (15)	0.0647 (15)	0.0099 (12)	0.0025 (12)	0.0237 (12)
C2	0.104 (3)	0.0676 (18)	0.0684 (18)	−0.0049 (18)	0.0198 (18)	0.0170 (15)
C3	0.139 (4)	0.0565 (17)	0.0603 (18)	0.003 (2)	0.009 (2)	0.0129 (14)
C4	0.119 (3)	0.080 (2)	0.083 (2)	0.029 (2)	−0.021 (2)	0.0185 (18)
C5	0.072 (2)	0.0768 (19)	0.0817 (19)	0.0125 (16)	−0.0042 (16)	0.0169 (17)
C6	0.0641 (17)	0.0455 (13)	0.0498 (13)	0.0016 (12)	0.0016 (12)	0.0050 (11)
C7	0.0664 (17)	0.0526 (14)	0.0582 (15)	−0.0008 (12)	0.0042 (13)	0.0080 (12)
C8	0.0451 (13)	0.0403 (12)	0.0533 (13)	0.0017 (10)	0.0039 (10)	0.0122 (10)
C9	0.0575 (15)	0.0398 (12)	0.0517 (13)	0.0046 (10)	0.0032 (11)	0.0039 (10)
C10	0.0536 (15)	0.0373 (12)	0.0597 (14)	0.0038 (10)	0.0042 (11)	0.0084 (10)
C11	0.0387 (12)	0.0431 (12)	0.0546 (13)	0.0029 (10)	0.0033 (10)	0.0103 (10)
C12	0.0539 (15)	0.0441 (13)	0.0536 (14)	0.0028 (11)	0.0021 (11)	−0.0002 (11)
C13	0.0602 (16)	0.0339 (11)	0.0601 (14)	0.0003 (10)	0.0026 (12)	0.0060 (11)
C14	0.0452 (14)	0.0457 (12)	0.0540 (13)	0.0056 (10)	−0.0004 (11)	0.0068 (10)
C15	0.0439 (13)	0.0522 (14)	0.0543 (14)	0.0073 (11)	0.0045 (11)	0.0119 (11)
C16	0.0590 (16)	0.0521 (15)	0.0595 (15)	0.0054 (12)	0.0057 (12)	0.0170 (13)
C17	0.0525 (15)	0.0530 (14)	0.0597 (16)	0.0086 (11)	0.0005 (12)	0.0191 (12)

O—C8	1.348 (3)	C7—H7B	0.9700
O—C7	1.441 (3)	C8—C13	1.388 (3)
N1—C16	1.146 (3)	C8—C9	1.405 (3)
C1—C2	1.373 (4)	C9—C10	1.374 (3)
C1—C6	1.385 (4)	C9—H9A	0.9300
C1—H1A	0.9300	C10—C11	1.405 (3)
N2—C17	1.140 (3)	C10—H10A	0.9300
C2—C3	1.337 (5)	C11—C12	1.413 (3)
C2—H2A	0.9300	C11—C14	1.437 (3)
C3—C4	1.374 (5)	C12—C13	1.362 (3)
C3—H3A	0.9300	C12—H12A	0.9300
C4—C5	1.401 (5)	C13—H13A	0.9300
C4—H4A	0.9300	C14—C15	1.356 (3)
C5—C6	1.376 (4)	C14—H14A	0.9300
C5—H5A	0.9300	C15—C16	1.434 (4)
C6—C7	1.495 (3)	C15—C17	1.434 (4)
C7—H7A	0.9700
C8—O—C7	119.02 (18)	O—C8—C9	125.1 (2)
C2—C1—C6	120.6 (3)	C13—C8—C9	119.4 (2)
C2—C1—H1A	119.7	C10—C9—C8	119.9 (2)
C6—C1—H1A	119.7	C10—C9—H9A	120.1
C3—C2—C1	120.6 (3)	C8—C9—H9A	120.1
C3—C2—H2A	119.7	C9—C10—C11	121.6 (2)
C1—C2—H2A	119.7	C9—C10—H10A	119.2
C2—C3—C4	120.7 (3)	C11—C10—H10A	119.2
C2—C3—H3A	119.7	C10—C11—C12	116.8 (2)
C4—C3—H3A	119.7	C10—C11—C14	126.4 (2)
C3—C4—C5	119.7 (3)	C12—C11—C14	116.7 (2)
C3—C4—H4A	120.2	C13—C12—C11	122.0 (2)
C5—C4—H4A	120.2	C13—C12—H12A	119.0
C6—C5—C4	119.5 (3)	C11—C12—H12A	119.0
C6—C5—H5A	120.3	C12—C13—C8	120.3 (2)
C4—C5—H5A	120.3	C12—C13—H13A	119.9
C5—C6—C1	119.0 (3)	C8—C13—H13A	119.9
C5—C6—C7	121.2 (3)	C15—C14—C11	132.4 (2)
C1—C6—C7	119.8 (2)	C15—C14—H14A	113.8
O—C7—C6	107.69 (19)	C11—C14—H14A	113.8
O—C7—H7A	110.2	C14—C15—C16	125.0 (2)
C6—C7—H7A	110.2	C14—C15—C17	119.1 (2)
O—C7—H7B	110.2	C16—C15—C17	115.9 (2)
C6—C7—H7B	110.2	N1—C16—C15	178.1 (3)
H7A—C7—H7B	108.5	N2—C17—C15	178.5 (3)
O—C8—C13	115.49 (19)
C6—C1—C2—C3	−0.4 (4)	C13—C8—C9—C10	0.0 (4)
C1—C2—C3—C4	0.0 (5)	C8—C9—C10—C11	0.2 (4)
C2—C3—C4—C5	0.3 (5)	C9—C10—C11—C12	−0.3 (3)
C3—C4—C5—C6	−0.1 (5)	C9—C10—C11—C14	−179.6 (2)
C4—C5—C6—C1	−0.4 (4)	C10—C11—C12—C13	0.1 (3)
C4—C5—C6—C7	−177.8 (2)	C14—C11—C12—C13	179.5 (2)
C2—C1—C6—C5	0.6 (4)	C11—C12—C13—C8	0.1 (4)
C2—C1—C6—C7	178.1 (2)	O—C8—C13—C12	179.3 (2)
C8—O—C7—C6	175.8 (2)	C9—C8—C13—C12	−0.2 (4)
C5—C6—C7—O	84.0 (3)	C10—C11—C14—C15	−0.5 (4)
C1—C6—C7—O	−93.4 (3)	C12—C11—C14—C15	−179.8 (2)
C7—O—C8—C13	−179.1 (2)	C11—C14—C15—C16	0.3 (4)
C7—O—C8—C9	0.4 (3)	C11—C14—C15—C17	179.4 (2)
O—C8—C9—C10	−179.4 (2)