Crystal structure of 2-[2-(benz-yloxy)benzyl-idene]malono-nitrile.

In the title benzyl-idenemalono-nitrile derivative, C17H12N2O, the dihedral angles between the central benzene ring and the Y-shaped C=C(CN)2 group (r.m.s. deviation = 0.006 Å) and the terminal benzene ring are 12.72 (8) and 37.60 (11)°, respectively. The Car-O-Csp (3)-Car torsion angle is -174.52 (13)° and the major twist between the aromatic rings occurs about the Csp (3)-Car bond. Weak aromatic π-π stacking [centroid-centroid separation = 3.7784 (13) Å; slippage = 1.21 Å] between inversion-related pairs of the central benzene rings is observed in the crystal.

Related literature

For the applications and biological activities of benzyl­idenemalono­nitrile derivatives, see: Turpaev et al. (2011 ▸); Sagara et al. (2002 ▸); Novogrodsky et al. (1994 ▸); Gazit et al. (1989 ▸). For the crystal structure of a related compound, see: Gan et al. (2012 ▸).

Experimental

Crystal data

C17H12N2O

M = 260.29

Triclinic,

a = 7.2959 (9) Å

b = 9.4963 (12) Å

c = 11.0280 (14) Å

α = 97.709 (3)°

β = 107.953 (3)°

γ = 105.155 (3)°

V = 682.13 (15) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 293 K

0.34 × 0.11 × 0.07 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▸) T min = 0.973, T max = 0.994

7776 measured reflections

2545 independent reflections

1722 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.112

S = 1.01

2545 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.11 e Å−3

Δρmin = −0.17 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 datablock(s) global, I. DOI: 10.1107/S2056989015012608/hb7442sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015012608/hb7442Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015012608/hb7442Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015012608/hb7442fig1.tif

The mol­ecular structure of (I) with displacement ellipsoids drawn at 30% probability level.

Click here for additional data file.

. DOI: 10.1107/S2056989015012608/hb7442fig2.tif

The crystal packing of the title compound (I).

CCDC reference: 1409734

Additional supporting information: crystallographic information; 3D view; checkCIF report

C17H12N2O	Z = 2
Mr = 260.29	F(000) = 272
Triclinic, P1	Dx = 1.267 Mg m−3
a = 7.2959 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.4963 (12) Å	Cell parameters from 1299 reflections
c = 11.0280 (14) Å	θ = 2.3–20.8°
α = 97.709 (3)°	µ = 0.08 mm−1
β = 107.953 (3)°	T = 293 K
γ = 105.155 (3)°	Plate, colourless
V = 682.13 (15) Å3	0.34 × 0.11 × 0.07 mm

Bruker SMART APEX CCD diffractometer	2545 independent reflections
Radiation source: fine-focus sealed tube	1722 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
ω scan	θmax = 25.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −8→8
Tmin = 0.973, Tmax = 0.994	k = −11→11
7776 measured reflections	l = −13→13

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0495P)2 + 0.016P] where P = (Fo2 + 2Fc2)/3
2545 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.11 e Å−3
0 restraints	Δρmin = −0.17 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
O1	0.37248 (18)	0.70351 (12)	0.15139 (10)	0.0558 (3)
N1	−0.0533 (3)	0.06530 (19)	0.15041 (17)	0.0861 (6)
N2	0.2682 (3)	0.38995 (18)	0.52272 (16)	0.0799 (6)
C1	0.6578 (3)	0.9358 (2)	0.36642 (19)	0.0682 (6)
H1A	0.6704	0.8409	0.3666	0.082*
C2	0.7541 (3)	1.0476 (3)	0.4799 (2)	0.0840 (7)
H2A	0.8300	1.0276	0.5565	0.101*
C3	0.7382 (4)	1.1883 (3)	0.4800 (2)	0.0864 (7)
H3A	0.8036	1.2639	0.5565	0.104*
C4	0.6260 (3)	1.2171 (2)	0.3675 (2)	0.0816 (7)
H4A	0.6163	1.3127	0.3670	0.098*
C5	0.5273 (3)	1.1043 (2)	0.2549 (2)	0.0653 (5)
H5A	0.4487	1.1241	0.1792	0.078*
C6	0.5432 (3)	0.96316 (18)	0.25284 (17)	0.0501 (4)
C7	0.4489 (3)	0.84695 (18)	0.12655 (17)	0.0573 (5)
H7A	0.3388	0.8708	0.0666	0.069*
H7B	0.5495	0.8453	0.0863	0.069*
C8	0.2956 (2)	0.57991 (18)	0.05089 (15)	0.0459 (4)
C9	0.2793 (3)	0.5848 (2)	−0.07670 (16)	0.0545 (5)
H9A	0.3218	0.6764	−0.0978	0.065*
C10	0.2002 (3)	0.4537 (2)	−0.17214 (17)	0.0607 (5)
H10A	0.1902	0.4575	−0.2577	0.073*
C11	0.1356 (3)	0.3172 (2)	−0.14330 (17)	0.0609 (5)
H11A	0.0824	0.2293	−0.2088	0.073*
C12	0.1501 (3)	0.31157 (19)	−0.01748 (16)	0.0539 (5)
H12A	0.1061	0.2189	0.0016	0.065*
C13	0.2296 (2)	0.44161 (17)	0.08304 (15)	0.0440 (4)
C14	0.2524 (2)	0.44280 (18)	0.21768 (15)	0.0478 (4)
H14A	0.3315	0.5343	0.2765	0.057*
C15	0.1784 (2)	0.33340 (18)	0.27265 (15)	0.0473 (4)
C16	0.0496 (3)	0.1845 (2)	0.20382 (17)	0.0568 (5)
C17	0.2273 (3)	0.36414 (19)	0.41193 (19)	0.0569 (5)

	U11	U22	U33	U12	U13	U23
O1	0.0745 (8)	0.0390 (7)	0.0461 (7)	0.0046 (6)	0.0232 (6)	0.0091 (5)
N1	0.1044 (15)	0.0552 (11)	0.0784 (12)	−0.0080 (10)	0.0388 (11)	0.0033 (9)
N2	0.1137 (15)	0.0664 (11)	0.0508 (11)	0.0125 (10)	0.0309 (10)	0.0144 (9)
C1	0.0809 (14)	0.0509 (12)	0.0639 (13)	0.0202 (10)	0.0152 (11)	0.0126 (10)
C2	0.0897 (17)	0.0751 (16)	0.0632 (14)	0.0207 (13)	0.0055 (12)	0.0023 (12)
C3	0.0827 (16)	0.0622 (15)	0.0862 (17)	0.0083 (12)	0.0189 (13)	−0.0159 (12)
C4	0.0847 (16)	0.0464 (12)	0.1071 (19)	0.0192 (11)	0.0332 (14)	0.0030 (13)
C5	0.0673 (13)	0.0491 (12)	0.0790 (14)	0.0183 (10)	0.0248 (11)	0.0177 (10)
C6	0.0521 (10)	0.0404 (10)	0.0562 (11)	0.0086 (8)	0.0221 (9)	0.0121 (8)
C7	0.0675 (12)	0.0448 (10)	0.0564 (11)	0.0114 (9)	0.0205 (9)	0.0190 (9)
C8	0.0448 (10)	0.0475 (10)	0.0404 (9)	0.0099 (8)	0.0146 (8)	0.0060 (8)
C9	0.0587 (11)	0.0578 (11)	0.0459 (10)	0.0130 (9)	0.0207 (9)	0.0156 (9)
C10	0.0634 (12)	0.0778 (14)	0.0382 (10)	0.0178 (10)	0.0198 (9)	0.0113 (10)
C11	0.0663 (12)	0.0603 (12)	0.0443 (11)	0.0099 (10)	0.0189 (9)	−0.0025 (9)
C12	0.0577 (11)	0.0464 (10)	0.0484 (11)	0.0070 (9)	0.0179 (9)	0.0039 (8)
C13	0.0444 (9)	0.0430 (9)	0.0389 (9)	0.0090 (7)	0.0128 (7)	0.0066 (7)
C14	0.0526 (10)	0.0394 (9)	0.0424 (10)	0.0084 (8)	0.0124 (8)	0.0044 (7)
C15	0.0540 (10)	0.0416 (10)	0.0410 (9)	0.0092 (8)	0.0163 (8)	0.0068 (8)
C16	0.0674 (12)	0.0461 (11)	0.0522 (11)	0.0064 (10)	0.0250 (9)	0.0108 (9)
C17	0.0716 (13)	0.0442 (11)	0.0508 (12)	0.0083 (9)	0.0242 (10)	0.0123 (9)

O1—C8	1.3580 (18)	C7—H7B	0.9700
O1—C7	1.4277 (18)	C8—C9	1.383 (2)
N1—C16	1.138 (2)	C8—C13	1.408 (2)
N2—C17	1.140 (2)	C9—C10	1.374 (2)
C1—C6	1.375 (2)	C9—H9A	0.9300
C1—C2	1.378 (3)	C10—C11	1.374 (2)
C1—H1A	0.9300	C10—H10A	0.9300
C2—C3	1.371 (3)	C11—C12	1.368 (2)
C2—H2A	0.9300	C11—H11A	0.9300
C3—C4	1.366 (3)	C12—C13	1.397 (2)
C3—H3A	0.9300	C12—H12A	0.9300
C4—C5	1.377 (3)	C13—C14	1.440 (2)
C4—H4A	0.9300	C14—C15	1.348 (2)
C5—C6	1.373 (2)	C14—H14A	0.9300
C5—H5A	0.9300	C15—C16	1.427 (2)
C6—C7	1.494 (2)	C15—C17	1.435 (2)
C7—H7A	0.9700
C8—O1—C7	118.82 (13)	O1—C8—C13	115.91 (14)
C6—C1—C2	120.69 (18)	C9—C8—C13	120.32 (15)
C6—C1—H1A	119.7	C10—C9—C8	119.76 (17)
C2—C1—H1A	119.7	C10—C9—H9A	120.1
C3—C2—C1	120.0 (2)	C8—C9—H9A	120.1
C3—C2—H2A	120.0	C9—C10—C11	121.12 (16)
C1—C2—H2A	120.0	C9—C10—H10A	119.4
C4—C3—C2	119.8 (2)	C11—C10—H10A	119.4
C4—C3—H3A	120.1	C12—C11—C10	119.45 (16)
C2—C3—H3A	120.1	C12—C11—H11A	120.3
C3—C4—C5	119.9 (2)	C10—C11—H11A	120.3
C3—C4—H4A	120.0	C11—C12—C13	121.61 (16)
C5—C4—H4A	120.0	C11—C12—H12A	119.2
C6—C5—C4	121.0 (2)	C13—C12—H12A	119.2
C6—C5—H5A	119.5	C12—C13—C8	117.74 (15)
C4—C5—H5A	119.5	C12—C13—C14	124.20 (15)
C5—C6—C1	118.55 (17)	C8—C13—C14	118.05 (14)
C5—C6—C7	119.67 (17)	C15—C14—C13	130.76 (15)
C1—C6—C7	121.64 (16)	C15—C14—H14A	114.6
O1—C7—C6	109.28 (14)	C13—C14—H14A	114.6
O1—C7—H7A	109.8	C14—C15—C16	125.63 (15)
C6—C7—H7A	109.8	C14—C15—C17	119.51 (15)
O1—C7—H7B	109.8	C16—C15—C17	114.86 (14)
C6—C7—H7B	109.8	N1—C16—C15	179.11 (19)
H7A—C7—H7B	108.3	N2—C17—C15	179.2 (2)
O1—C8—C9	123.76 (15)
C6—C1—C2—C3	−0.7 (3)	C9—C10—C11—C12	0.1 (3)
C1—C2—C3—C4	0.2 (4)	C10—C11—C12—C13	−0.1 (3)
C2—C3—C4—C5	0.8 (4)	C11—C12—C13—C8	−0.3 (2)
C3—C4—C5—C6	−1.4 (3)	C11—C12—C13—C14	−178.75 (16)
C4—C5—C6—C1	0.9 (3)	O1—C8—C13—C12	−179.77 (14)
C4—C5—C6—C7	−174.84 (18)	C9—C8—C13—C12	0.6 (2)
C2—C1—C6—C5	0.2 (3)	O1—C8—C13—C14	−1.2 (2)
C2—C1—C6—C7	175.84 (19)	C9—C8—C13—C14	179.23 (15)
C8—O1—C7—C6	−174.52 (13)	C12—C13—C14—C15	−12.2 (3)
C5—C6—C7—O1	−144.67 (16)	C8—C13—C14—C15	169.29 (17)
C1—C6—C7—O1	39.7 (2)	C13—C14—C15—C16	−1.5 (3)
C7—O1—C8—C9	−2.6 (2)	C13—C14—C15—C17	179.08 (17)
C7—O1—C8—C13	177.82 (14)	C14—C15—C16—N1	−176 (100)
O1—C8—C9—C10	179.76 (15)	C17—C15—C16—N1	3 (14)
C13—C8—C9—C10	−0.7 (2)	C14—C15—C17—N2	−22 (16)
C8—C9—C10—C11	0.3 (3)	C16—C15—C17—N2	159 (16)