4,4'-(Oxydimethyl-ene)dibenzonitrile.

The title compound, C(16)H(12)N(2)O, was accidentally synthesized by the reaction of 4-(bromo-meth-yl)benzonitrile and penta-erythritol. The dihedral angle between the benzene rings is 57.39 (9)°. In the crystal structure, mol-ecules are linked by inter-molecular C-H⋯N hydrogen-bonding inter-actions to form chains running parallel to the b axis.

Related literature

For applications of nitrile derivatives in the synthesis of some heterocyclic mol­ecules, see: Radl et al. (2000 ▶); Jin et al. (1994 ▶). For the crystal structure of a related compound, see: Fu & Zhao (2007 ▶).

Experimental

Crystal data

C16H12N2O

M = 248.28

Monoclinic,

a = 14.444 (3) Å

b = 7.6674 (13) Å

c = 11.897 (2) Å

β = 96.326 (14)°

V = 1309.6 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 (2) K

0.35 × 0.30 × 0.30 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.939, T max = 0.978

13064 measured reflections

3007 independent reflections

1498 reflections with I > 2σ(I)

R int = 0.071

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.149

S = 1.01

3007 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.11 e Å−3

Δρmin = −0.15 e Å−3

Data collection: CrystalClear (Rigaku, 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/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808020527/rz2229sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020527/rz2229Isup2.hkl

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

C16H12N2O	F000 = 520
Mr = 248.28	Dx = 1.259 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1930 reflections
a = 14.444 (3) Å	θ = 2.8–27.5º
b = 7.6674 (13) Å	µ = 0.08 mm−1
c = 11.897 (2) Å	T = 293 (2) K
β = 96.326 (14)º	Block, colourless
V = 1309.6 (4) Å3	0.35 × 0.30 × 0.30 mm
Z = 4

Rigaku Mercury2 diffractometer	3007 independent reflections
Radiation source: fine-focus sealed tube	1498 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.072
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5º
T = 293(2) K	θmin = 2.8º
ω scans	h = −18→18
Absorption correction: Multi-scan(CrystalClear; Rigaku, 2005)	k = −9→9
Tmin = 0.939, Tmax = 0.978	l = −15→15
13064 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.064	H-atom parameters constrained
wR(F2) = 0.149	w = 1/[σ2(Fo2) + (0.0573P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
3007 reflections	Δρmax = 0.11 e Å−3
172 parameters	Δρmin = −0.15 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.21121 (10)	0.2174 (2)	0.82830 (14)	0.0632 (5)
C13	0.40291 (15)	0.6678 (3)	1.0392 (2)	0.0543 (6)
C5	−0.05516 (16)	0.2145 (3)	0.5362 (2)	0.0530 (6)
C1	0.17453 (17)	0.0647 (3)	0.7737 (2)	0.0610 (7)
H1A	0.1547	−0.0163	0.8289	0.073*
H1B	0.2218	0.0082	0.7346	0.073*
C16	0.43912 (17)	0.8289 (4)	1.0896 (2)	0.0647 (7)
C3	0.10674 (17)	0.2247 (3)	0.6017 (2)	0.0616 (7)
H3	0.1662	0.2664	0.5941	0.074*
C2	0.09330 (16)	0.1156 (3)	0.69105 (19)	0.0505 (6)
C11	0.33163 (17)	0.5062 (3)	0.8811 (2)	0.0608 (7)
H11	0.3073	0.5020	0.8054	0.073*
C7	0.00448 (17)	0.0575 (3)	0.7016 (2)	0.0592 (7)
H7	−0.0057	−0.0156	0.7614	0.071*
C4	0.03367 (17)	0.2726 (3)	0.5241 (2)	0.0624 (7)
H4	0.0440	0.3439	0.4635	0.075*
C10	0.33245 (15)	0.3570 (3)	0.9471 (2)	0.0539 (6)
C6	−0.06975 (17)	0.1060 (3)	0.6249 (2)	0.0618 (7)
H6	−0.1294	0.0657	0.6331	0.074*
C9	0.29580 (16)	0.1870 (3)	0.8972 (2)	0.0659 (7)
H9A	0.3410	0.1358	0.8524	0.079*
H9B	0.2855	0.1062	0.9572	0.079*
C12	0.36687 (17)	0.6610 (3)	0.9274 (2)	0.0625 (7)
H12	0.3662	0.7608	0.8828	0.075*
C14	0.40499 (17)	0.5201 (3)	1.1048 (2)	0.0619 (7)
H14	0.4302	0.5241	1.1801	0.074*
C15	0.36940 (16)	0.3653 (3)	1.0584 (2)	0.0625 (7)
H15	0.3705	0.2657	1.1031	0.075*
C8	−0.13138 (19)	0.2686 (3)	0.4553 (2)	0.0640 (7)
N2	0.46806 (17)	0.9545 (3)	1.1316 (2)	0.0850 (8)
N1	−0.19108 (17)	0.3162 (3)	0.3912 (2)	0.0883 (8)

	U11	U22	U33	U12	U13	U23
O1	0.0528 (10)	0.0591 (10)	0.0733 (11)	0.0012 (8)	−0.0121 (8)	−0.0152 (8)
C13	0.0438 (13)	0.0670 (16)	0.0511 (15)	−0.0015 (11)	0.0004 (11)	−0.0064 (12)
C5	0.0529 (15)	0.0533 (14)	0.0521 (15)	0.0004 (11)	0.0024 (12)	−0.0107 (11)
C1	0.0591 (16)	0.0546 (15)	0.0677 (17)	−0.0037 (12)	0.0000 (13)	−0.0063 (12)
C16	0.0568 (16)	0.0752 (19)	0.0604 (17)	−0.0035 (13)	−0.0009 (13)	−0.0087 (14)
C3	0.0477 (15)	0.0689 (17)	0.0690 (17)	−0.0086 (12)	0.0107 (13)	0.0035 (13)
C2	0.0524 (14)	0.0463 (13)	0.0527 (15)	−0.0039 (11)	0.0050 (11)	−0.0096 (11)
C11	0.0572 (16)	0.0742 (18)	0.0479 (15)	−0.0013 (12)	−0.0078 (12)	−0.0039 (13)
C7	0.0594 (16)	0.0601 (16)	0.0586 (16)	−0.0125 (12)	0.0082 (13)	−0.0004 (12)
C4	0.0607 (17)	0.0676 (17)	0.0600 (16)	−0.0025 (13)	0.0117 (13)	0.0057 (12)
C10	0.0405 (13)	0.0632 (16)	0.0567 (15)	0.0052 (11)	−0.0002 (11)	−0.0076 (12)
C6	0.0525 (15)	0.0656 (17)	0.0678 (17)	−0.0138 (12)	0.0086 (13)	−0.0060 (13)
C9	0.0538 (15)	0.0664 (17)	0.0743 (18)	0.0051 (12)	−0.0065 (13)	−0.0083 (13)
C12	0.0646 (16)	0.0652 (17)	0.0558 (16)	−0.0057 (13)	−0.0020 (13)	0.0029 (12)
C14	0.0548 (16)	0.0772 (19)	0.0508 (15)	0.0023 (13)	−0.0072 (12)	−0.0038 (13)
C15	0.0580 (15)	0.0650 (17)	0.0619 (17)	0.0042 (12)	−0.0044 (13)	0.0063 (13)
C8	0.0621 (17)	0.0638 (17)	0.0654 (18)	−0.0015 (13)	0.0041 (14)	−0.0083 (13)
N2	0.0928 (19)	0.0813 (18)	0.0772 (17)	−0.0108 (14)	−0.0071 (14)	−0.0135 (14)
N1	0.0732 (16)	0.0958 (18)	0.0919 (19)	0.0035 (14)	−0.0094 (14)	0.0044 (15)

O1—C9	1.414 (3)	C11—C12	1.382 (3)
O1—C1	1.414 (2)	C11—C10	1.387 (3)
C13—C14	1.374 (3)	C11—H11	0.9300
C13—C12	1.375 (3)	C7—C6	1.380 (3)
C13—C16	1.445 (3)	C7—H7	0.9300
C5—C6	1.379 (3)	C4—H4	0.9300
C5—C4	1.380 (3)	C10—C15	1.373 (3)
C5—C8	1.441 (3)	C10—C9	1.504 (3)
C1—C2	1.497 (3)	C6—H6	0.9300
C1—H1A	0.9700	C9—H9A	0.9700
C1—H1B	0.9700	C9—H9B	0.9700
C16—N2	1.142 (3)	C12—H12	0.9300
C3—C4	1.374 (3)	C14—C15	1.384 (3)
C3—C2	1.384 (3)	C14—H14	0.9300
C3—H3	0.9300	C15—H15	0.9300
C2—C7	1.377 (3)	C8—N1	1.145 (3)
C9—O1—C1	112.70 (17)	C3—C4—C5	119.9 (2)
C14—C13—C12	120.0 (2)	C3—C4—H4	120.1
C14—C13—C16	119.0 (2)	C5—C4—H4	120.1
C12—C13—C16	121.0 (2)	C15—C10—C11	119.1 (2)
C6—C5—C4	119.8 (2)	C15—C10—C9	120.2 (2)
C6—C5—C8	121.0 (2)	C11—C10—C9	120.7 (2)
C4—C5—C8	119.2 (2)	C5—C6—C7	119.7 (2)
O1—C1—C2	108.22 (18)	C5—C6—H6	120.1
O1—C1—H1A	110.1	C7—C6—H6	120.1
C2—C1—H1A	110.1	O1—C9—C10	109.29 (19)
O1—C1—H1B	110.1	O1—C9—H9A	109.8
C2—C1—H1B	110.1	C10—C9—H9A	109.8
H1A—C1—H1B	108.4	O1—C9—H9B	109.8
N2—C16—C13	178.5 (3)	C10—C9—H9B	109.8
C4—C3—C2	121.0 (2)	H9A—C9—H9B	108.3
C4—C3—H3	119.5	C13—C12—C11	120.1 (2)
C2—C3—H3	119.5	C13—C12—H12	119.9
C7—C2—C3	118.5 (2)	C11—C12—H12	119.9
C7—C2—C1	121.8 (2)	C13—C14—C15	119.8 (2)
C3—C2—C1	119.7 (2)	C13—C14—H14	120.1
C12—C11—C10	120.2 (2)	C15—C14—H14	120.1
C12—C11—H11	119.9	C10—C15—C14	120.8 (2)
C10—C11—H11	119.9	C10—C15—H15	119.6
C2—C7—C6	121.1 (2)	C14—C15—H15	119.6
C2—C7—H7	119.4	N1—C8—C5	178.1 (3)
C6—C7—H7	119.4

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···N2i	0.93	2.60	3.490 (3)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯N2i	0.93	2.60	3.490 (3)	162

Symmetry code: (i) .