4-(4-Cyano-benzoyl-meth-yl)benzonitrile.

In the title compound, C(16)H(10)N(2)O, the dihedral angle formed by the benzene rings is 84.99 (7)°. The crystal structure is stabilized by inter-molecular C-H⋯N and C-H⋯O hydrogen-bond inter-actions, forming chains running parallel to the b axis.

Related literature

For related literature, see: Arıcı et al. (2004 ▶); Radl et al. (2000 ▶); Bernstein et al. (1995 ▶); Zhao (2008 ▶).

Experimental

Crystal data

C16H10N2O

M = 246.26

Triclinic,

a = 7.5217 (15) Å

b = 7.9759 (16) Å

c = 10.881 (2) Å

α = 96.78 (3)°

β = 93.34 (3)°

γ = 102.10 (3)°

V = 631.5 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 293 (2) K

0.20 × 0.20 × 0.16 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.964, T max = 0.988

6576 measured reflections

2898 independent reflections

1943 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.157

S = 1.04

2898 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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/S1600536808015079/rz2215sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808015079/rz2215Isup2.hkl

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

C16H10N2O	Z = 2
Mr = 246.26	F000 = 256
Triclinic, P1	Dx = 1.295 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 7.5217 (15) Å	Cell parameters from 2232 reflections
b = 7.9759 (16) Å	θ = 3.0–27.4º
c = 10.881 (2) Å	µ = 0.08 mm−1
α = 96.78 (3)º	T = 293 (2) K
β = 93.34 (3)º	Block, yellow
γ = 102.10 (3)º	0.20 × 0.20 × 0.16 mm
V = 631.5 (2) Å3

Rigaku Mercury2 diffractometer	2898 independent reflections
Radiation source: fine-focus sealed tube	1943 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.028
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5º
T = 293(2) K	θmin = 3.0º
CCD_Profile_fitting scans	h = −9→9
Absorption correction: Multi-scan(CrystalClear; Rigaku/MSC, 2005)	k = −10→10
Tmin = 0.964, Tmax = 0.988	l = −14→14
6576 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.059	w = 1/[σ2(Fo2) + (0.0717P)2 + 0.1009P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.157	(Δ/σ)max = 0.002
S = 1.04	Δρmax = 0.25 e Å−3
2898 reflections	Δρmin = −0.21 e Å−3
173 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.168 (18)
Secondary atom site location: difference Fourier map

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
C1	0.1774 (2)	0.4661 (2)	0.18751 (15)	0.0468 (4)
C2	0.0347 (3)	0.5506 (2)	0.18255 (17)	0.0546 (5)
H2	−0.0715	0.5081	0.2189	0.066*
C3	0.0475 (3)	0.6970 (2)	0.12455 (17)	0.0532 (5)
H3	−0.0493	0.7528	0.1218	0.064*
C4	0.2055 (2)	0.7599 (2)	0.07065 (15)	0.0468 (4)
C5	0.3487 (3)	0.6762 (2)	0.07410 (17)	0.0550 (5)
H5	0.4545	0.7181	0.0371	0.066*
C6	0.3339 (3)	0.5301 (2)	0.13273 (17)	0.0550 (5)
H6	0.4306	0.4742	0.1353	0.066*
C7	0.2217 (3)	0.9131 (2)	0.00999 (17)	0.0558 (5)
C8	0.2389 (2)	0.2017 (2)	0.46012 (15)	0.0457 (4)
C9	0.2979 (3)	0.2430 (2)	0.58529 (16)	0.0580 (5)
H9	0.3178	0.3571	0.6226	0.070*
C10	0.3274 (3)	0.1162 (2)	0.65476 (17)	0.0599 (5)
H10	0.3668	0.1447	0.7387	0.072*
C11	0.2980 (2)	−0.0536 (2)	0.59929 (16)	0.0476 (4)
C12	0.2369 (2)	−0.0974 (2)	0.47534 (17)	0.0521 (5)
H12	0.2158	−0.2118	0.4384	0.062*
C13	0.2074 (3)	0.0309 (2)	0.40669 (16)	0.0508 (5)
H13	0.1656	0.0018	0.3232	0.061*
C14	0.3367 (3)	−0.1839 (2)	0.67244 (18)	0.0560 (5)
C15	0.2138 (3)	0.3455 (2)	0.38867 (17)	0.0589 (5)
N1	0.2355 (3)	1.0349 (2)	−0.03745 (18)	0.0757 (5)
N2	0.3690 (3)	−0.2834 (2)	0.73238 (17)	0.0742 (6)
O1	0.2335 (4)	0.48933 (19)	0.44054 (14)	0.1312 (10)
C16	0.1648 (3)	0.3057 (2)	0.25106 (16)	0.0529 (5)
H16A	0.0413	0.2365	0.2358	0.063*
H16B	0.2458	0.2374	0.2147	0.063*

	U11	U22	U33	U12	U13	U23
C1	0.0585 (11)	0.0387 (8)	0.0433 (9)	0.0106 (8)	−0.0022 (8)	0.0092 (7)
C2	0.0563 (11)	0.0512 (10)	0.0595 (11)	0.0119 (9)	0.0080 (9)	0.0189 (9)
C3	0.0581 (11)	0.0491 (10)	0.0585 (11)	0.0204 (8)	0.0042 (9)	0.0166 (8)
C4	0.0600 (11)	0.0400 (8)	0.0405 (8)	0.0105 (8)	−0.0016 (8)	0.0090 (7)
C5	0.0575 (11)	0.0531 (10)	0.0572 (11)	0.0126 (9)	0.0064 (9)	0.0171 (9)
C6	0.0573 (11)	0.0531 (10)	0.0592 (11)	0.0196 (9)	0.0014 (9)	0.0142 (9)
C7	0.0694 (13)	0.0504 (10)	0.0516 (10)	0.0168 (9)	0.0060 (9)	0.0153 (8)
C8	0.0579 (10)	0.0367 (8)	0.0456 (9)	0.0140 (7)	0.0060 (8)	0.0104 (7)
C9	0.0864 (14)	0.0370 (9)	0.0500 (10)	0.0134 (9)	0.0019 (10)	0.0055 (8)
C10	0.0798 (14)	0.0507 (10)	0.0478 (10)	0.0099 (10)	−0.0036 (9)	0.0133 (8)
C11	0.0474 (9)	0.0431 (9)	0.0569 (10)	0.0109 (7)	0.0092 (8)	0.0212 (8)
C12	0.0656 (12)	0.0330 (8)	0.0596 (11)	0.0121 (8)	0.0076 (9)	0.0106 (8)
C13	0.0668 (11)	0.0378 (9)	0.0486 (10)	0.0132 (8)	0.0022 (8)	0.0073 (7)
C14	0.0566 (11)	0.0512 (10)	0.0661 (12)	0.0144 (9)	0.0103 (9)	0.0243 (9)
C15	0.0930 (15)	0.0367 (9)	0.0514 (10)	0.0225 (9)	0.0028 (10)	0.0108 (8)
N1	0.0880 (13)	0.0672 (11)	0.0853 (13)	0.0269 (10)	0.0212 (10)	0.0399 (10)
N2	0.0837 (13)	0.0672 (11)	0.0843 (13)	0.0263 (10)	0.0116 (10)	0.0410 (10)
O1	0.296 (3)	0.0429 (8)	0.0603 (10)	0.0630 (13)	−0.0189 (13)	0.0018 (7)
C16	0.0680 (12)	0.0387 (9)	0.0527 (10)	0.0126 (8)	−0.0010 (9)	0.0108 (8)

C1—C6	1.380 (3)	C8—C15	1.496 (2)
C1—C2	1.383 (2)	C9—C10	1.377 (2)
C1—C16	1.513 (2)	C9—H9	0.9300
C2—C3	1.381 (2)	C10—C11	1.384 (3)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.381 (3)	C11—C12	1.379 (2)
C3—H3	0.9300	C11—C14	1.446 (2)
C4—C5	1.382 (3)	C12—C13	1.382 (2)
C4—C7	1.442 (2)	C12—H12	0.9300
C5—C6	1.381 (2)	C13—H13	0.9300
C5—H5	0.9300	C14—N2	1.140 (2)
C6—H6	0.9300	C15—O1	1.193 (2)
C7—N1	1.142 (2)	C15—C16	1.501 (3)
C8—C13	1.383 (2)	C16—H16A	0.9700
C8—C9	1.387 (2)	C16—H16B	0.9700
C6—C1—C2	118.89 (15)	C8—C9—H9	119.7
C6—C1—C16	119.65 (16)	C9—C10—C11	119.80 (17)
C2—C1—C16	121.46 (16)	C9—C10—H10	120.1
C3—C2—C1	121.07 (17)	C11—C10—H10	120.1
C3—C2—H2	119.5	C12—C11—C10	120.45 (15)
C1—C2—H2	119.5	C12—C11—C14	120.50 (16)
C2—C3—C4	119.32 (17)	C10—C11—C14	119.03 (17)
C2—C3—H3	120.3	C11—C12—C13	119.21 (16)
C4—C3—H3	120.3	C11—C12—H12	120.4
C3—C4—C5	120.28 (15)	C13—C12—H12	120.4
C3—C4—C7	120.13 (16)	C12—C13—C8	121.10 (17)
C5—C4—C7	119.59 (16)	C12—C13—H13	119.5
C6—C5—C4	119.70 (17)	C8—C13—H13	119.5
C6—C5—H5	120.2	N2—C14—C11	178.3 (2)
C4—C5—H5	120.2	O1—C15—C8	120.30 (17)
C1—C6—C5	120.74 (17)	O1—C15—C16	120.78 (16)
C1—C6—H6	119.6	C8—C15—C16	118.92 (15)
C5—C6—H6	119.6	C15—C16—C1	113.15 (14)
N1—C7—C4	179.5 (2)	C15—C16—H16A	108.9
C13—C8—C9	118.91 (15)	C1—C16—H16A	108.9
C13—C8—C15	122.97 (16)	C15—C16—H16B	108.9
C9—C8—C15	118.12 (15)	C1—C16—H16B	108.9
C10—C9—C8	120.52 (16)	H16A—C16—H16B	107.8
C10—C9—H9	119.7

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N1i	0.93	2.62	3.486 (3)	154
C12—H12···O1ii	0.93	2.42	3.268 (2)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯N1i	0.93	2.62	3.486 (3)	154
C12—H12⋯O1ii	0.93	2.42	3.268 (2)	152

Symmetry codes: (i) ; (ii) .