2,2',6,6'-Tetra-ethyl-4,4'-methyl-enedibenzonitrile.

The asymmetric unit of the title compound, C(23)H(26)N(2), contains one half-mol-ecule, which is completed by the operation of a crystallographic twofold axis. In the mol-ecule, the two benzene rings form a dihedral angle of 77.09 (7)°.

Related literature

For applications of aromatic nitriles, see: Debasree et al. (2009 ▶); Lal Dhar et al. (2009 ▶); Ren et al. (2009 ▶); Zhou et al. (2009 ▶). For the preparation of the title compound, see: Donald et al. (1955 ▶).

Experimental

Crystal data

C23H26N2

M = 330.46

Monoclinic,

a = 16.016 (3) Å

b = 9.3218 (19) Å

c = 13.977 (3) Å

β = 115.55 (3)°

V = 1882.6 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 290 K

0.16 × 0.10 × 0.10 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer

8636 measured reflections

2055 independent reflections

1405 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.111

S = 1.16

2055 reflections

117 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1999 ▶); 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/S1600536810020052/cv2718sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810020052/cv2718Isup2.hkl

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

C23H26N2	F(000) = 712
Mr = 330.46	Dx = 1.166 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2049 reflections
a = 16.016 (3) Å	θ = 2.2–23.2°
b = 9.3218 (19) Å	µ = 0.07 mm−1
c = 13.977 (3) Å	T = 290 K
β = 115.55 (3)°	Block, colourless
V = 1882.6 (7) Å3	0.16 × 0.10 × 0.10 mm
Z = 4

Bruker SMART 4K CCD area-detector diffractometer	1405 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.028
graphite	θmax = 27.0°, θmin = 3.2°
phi and ω scans	h = −20→20
8636 measured reflections	k = −11→11
2055 independent reflections	l = −17→17

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)] = 0.038	H-atom parameters constrained
wR(F2) = 0.111	w = 1/[σ2(Fo2) + (0.0506P)2 + 0.6433P] where P = (Fo2 + 2Fc2)/3
S = 1.16	(Δ/σ)max = 0.003
2055 reflections	Δρmax = 0.24 e Å−3
117 parameters	Δρmin = −0.20 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0066 (13)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.15377 (8)	0.06614 (13)	0.12294 (10)	0.0215 (3)
C2	0.17923 (8)	0.06280 (13)	0.23286 (10)	0.0214 (3)
C3	0.12805 (8)	0.14471 (13)	0.27126 (10)	0.0217 (3)
H3	0.1444	0.1449	0.3437	0.026*
C4	0.05275 (8)	0.22672 (14)	0.20424 (10)	0.0222 (3)
C5	0.02799 (8)	0.22437 (14)	0.09566 (10)	0.0239 (3)
H5	−0.0233	0.2768	0.0504	0.029*
C6	0.07756 (8)	0.14604 (14)	0.05298 (10)	0.0227 (3)
C7	0.26297 (9)	−0.01923 (15)	0.30817 (10)	0.0254 (3)
H7A	0.2723	−0.1023	0.2721	0.030*
H7B	0.2524	−0.0530	0.3677	0.030*
C8	0.34907 (10)	0.07400 (17)	0.34864 (13)	0.0379 (4)
H8A	0.3615	0.1031	0.2902	0.057*
H8B	0.4008	0.0205	0.3984	0.057*
H8C	0.3394	0.1574	0.3829	0.057*
C9	0.20907 (9)	−0.01286 (15)	0.08264 (10)	0.0251 (3)
C10	0.05135 (9)	0.15086 (15)	−0.06463 (10)	0.0277 (3)
H10A	−0.0150	0.1648	−0.1028	0.033*
H10B	0.0664	0.0595	−0.0865	0.033*
C11	0.10057 (11)	0.26976 (19)	−0.09430 (12)	0.0392 (4)
H11A	0.0849	0.3607	−0.0742	0.059*
H11B	0.0817	0.2684	−0.1695	0.059*
H11C	0.1662	0.2554	−0.0580	0.059*
C12	0.0000	0.3165 (2)	0.2500	0.0265 (4)
H12	0.0432	0.3778	0.3053	0.032*
N1	0.25510 (9)	−0.07416 (14)	0.05233 (10)	0.0370 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0215 (6)	0.0215 (7)	0.0221 (6)	−0.0050 (5)	0.0099 (5)	−0.0016 (5)
C2	0.0203 (6)	0.0210 (7)	0.0229 (6)	−0.0039 (5)	0.0094 (5)	0.0005 (5)
C3	0.0223 (6)	0.0245 (7)	0.0183 (6)	−0.0037 (5)	0.0088 (5)	0.0003 (5)
C4	0.0203 (6)	0.0215 (6)	0.0263 (7)	−0.0048 (5)	0.0113 (5)	−0.0001 (5)
C5	0.0199 (6)	0.0241 (7)	0.0246 (7)	−0.0025 (5)	0.0066 (5)	0.0033 (5)
C6	0.0226 (6)	0.0235 (7)	0.0203 (6)	−0.0075 (5)	0.0077 (5)	0.0002 (5)
C7	0.0275 (7)	0.0270 (7)	0.0212 (7)	0.0034 (6)	0.0101 (6)	0.0026 (5)
C8	0.0263 (7)	0.0374 (9)	0.0385 (9)	0.0013 (6)	0.0031 (6)	0.0020 (7)
C9	0.0283 (7)	0.0266 (7)	0.0201 (6)	−0.0042 (6)	0.0102 (6)	−0.0004 (5)
C10	0.0273 (7)	0.0327 (8)	0.0195 (7)	−0.0039 (6)	0.0066 (6)	0.0002 (6)
C11	0.0393 (8)	0.0505 (10)	0.0266 (8)	−0.0096 (7)	0.0132 (7)	0.0069 (7)
C12	0.0255 (9)	0.0243 (10)	0.0309 (10)	0.000	0.0132 (8)	0.000
N1	0.0443 (7)	0.0378 (7)	0.0333 (7)	0.0020 (6)	0.0209 (6)	−0.0010 (6)

C1—C6	1.4040 (18)	C7—H7B	0.9700
C1—C2	1.4096 (18)	C8—H8A	0.9600
C1—C9	1.4402 (18)	C8—H8B	0.9600
C2—C3	1.3865 (18)	C8—H8C	0.9600
C2—C7	1.5079 (18)	C9—N1	1.1486 (17)
C3—C4	1.3935 (18)	C10—C11	1.5178 (19)
C3—H3	0.9300	C10—H10A	0.9700
C4—C5	1.3935 (18)	C10—H10B	0.9700
C4—C12	1.5129 (16)	C11—H11A	0.9600
C5—C6	1.3885 (19)	C11—H11B	0.9600
C5—H5	0.9300	C11—H11C	0.9600
C6—C10	1.5115 (18)	C12—C4i	1.5130 (16)
C7—C8	1.5179 (19)	C12—H12	0.9700
C7—H7A	0.9700
C6—C1—C2	121.79 (11)	H7A—C7—H7B	108.0
C6—C1—C9	119.69 (11)	C7—C8—H8A	109.5
C2—C1—C9	118.51 (11)	C7—C8—H8B	109.5
C3—C2—C1	117.92 (11)	H8A—C8—H8B	109.5
C3—C2—C7	120.36 (11)	C7—C8—H8C	109.5
C1—C2—C7	121.61 (11)	H8A—C8—H8C	109.5
C2—C3—C4	121.78 (12)	H8B—C8—H8C	109.5
C2—C3—H3	119.1	N1—C9—C1	178.28 (14)
C4—C3—H3	119.1	C6—C10—C11	112.67 (11)
C5—C4—C3	118.74 (12)	C6—C10—H10A	109.1
C5—C4—C12	121.37 (11)	C11—C10—H10A	109.1
C3—C4—C12	119.89 (10)	C6—C10—H10B	109.1
C6—C5—C4	121.96 (12)	C11—C10—H10B	109.1
C6—C5—H5	119.0	H10A—C10—H10B	107.8
C4—C5—H5	119.0	C10—C11—H11A	109.5
C5—C6—C1	117.78 (11)	C10—C11—H11B	109.5
C5—C6—C10	120.63 (12)	H11A—C11—H11B	109.5
C1—C6—C10	121.57 (12)	C10—C11—H11C	109.5
C2—C7—C8	111.18 (11)	H11A—C11—H11C	109.5
C2—C7—H7A	109.4	H11B—C11—H11C	109.5
C8—C7—H7A	109.4	C4—C12—C4i	112.85 (15)
C2—C7—H7B	109.4	C4—C12—H12	109.0
C8—C7—H7B	109.4
C6—C1—C2—C3	−1.79 (18)	C4—C5—C6—C10	−177.34 (11)
C9—C1—C2—C3	177.02 (11)	C2—C1—C6—C5	0.88 (18)
C6—C1—C2—C7	−177.97 (11)	C9—C1—C6—C5	−177.92 (11)
C9—C1—C2—C7	0.85 (18)	C2—C1—C6—C10	179.15 (11)
C1—C2—C3—C4	0.93 (18)	C9—C1—C6—C10	0.35 (18)
C7—C2—C3—C4	177.15 (11)	C3—C2—C7—C8	−86.55 (15)
C2—C3—C4—C5	0.80 (18)	C1—C2—C7—C8	89.53 (15)
C2—C3—C4—C12	−178.92 (11)	C5—C6—C10—C11	89.82 (15)
C3—C4—C5—C6	−1.77 (19)	C1—C6—C10—C11	−88.39 (15)
C12—C4—C5—C6	177.94 (12)	C5—C4—C12—C4i	112.50 (12)
C4—C5—C6—C1	0.94 (18)	C3—C4—C12—C4i	−67.79 (10)