4,4'-(1,8-Naphthalene-1,8-di-yl)dibenzonitrile.

In the title mol-ecule, C(24)H(14)N(2), the exterior C-C-C angle of the naphthalene ring system involving the two phenyl-substituted C atoms is 126.06 (11)° and the dihedral angles between the mean plane of the naphthalene ring system and those of the benzene rings are 66.63 (5) and 67.89 (5)°. In the crystal, mol-ecules are linked into a ladders by four weak C-H⋯π inter-actions.

Related literature

For the structure of the related compound 4-(1-napht­yl)benzonitrile, see: Lima et al. (2010 ▶).

Experimental

Crystal data

C24H14N2

M = 330.37

Monoclinic,

a = 17.0872 (9) Å

b = 8.2997 (4) Å

c = 24.3656 (13) Å

β = 93.795 (2)°

V = 3447.9 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 150 K

0.40 × 0.30 × 0.02 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.971, T max = 0.999

11422 measured reflections

4634 independent reflections

3482 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.131

S = 1.04

4634 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and OSCAIL (McArdle et al., 2004 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681005083X/lh5183sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681005083X/lh5183Isup2.hkl

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

C24H14N2	F(000) = 1376
Mr = 330.37	Dx = 1.273 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 205 reflections
a = 17.0872 (9) Å	θ = 7.4–29.2°
b = 8.2997 (4) Å	µ = 0.08 mm−1
c = 24.3656 (13) Å	T = 150 K
β = 93.795 (2)°	Plate, white
V = 3447.9 (3) Å3	0.40 × 0.30 × 0.02 mm
Z = 8

Bruker SMART APEX diffractometer	4634 independent reflections
Radiation source: fine-focus sealed tube	3482 reflections with I > 2σ(I)
graphite	Rint = 0.031
Detector resolution: 8.33 pixels mm-1	θmax = 29.2°, θmin = 3.0°
ω scans	h = −22→23
Absorption correction: multi-scan (SADABS; Bruker, 2004)	k = −11→6
Tmin = 0.971, Tmax = 0.999	l = −24→33
11422 measured reflections

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0635P)2 + 1.3141P] where P = (Fo2 + 2Fc2)/3
4634 reflections	(Δ/σ)max = 0.001
235 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.26 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
N14	0.69235 (9)	0.27151 (19)	0.76246 (5)	0.0427 (4)
N84	0.60515 (8)	0.8449 (2)	0.77878 (5)	0.0449 (4)
C1	0.64595 (7)	0.48335 (15)	0.49000 (5)	0.0182 (3)
C2	0.66041 (7)	0.35609 (16)	0.45575 (5)	0.0216 (3)
H2	0.6753	0.2553	0.4717	0.026*
C3	0.65391 (8)	0.36994 (17)	0.39800 (5)	0.0237 (3)
H3	0.6644	0.2800	0.3755	0.028*
C4	0.63235 (8)	0.51393 (17)	0.37489 (5)	0.0228 (3)
H4	0.6277	0.5238	0.3360	0.027*
C5	0.59492 (7)	0.79704 (17)	0.38171 (5)	0.0225 (3)
H5	0.5909	0.8029	0.3427	0.027*
C6	0.57980 (8)	0.93033 (17)	0.41173 (5)	0.0238 (3)
H6	0.5655	1.0288	0.3939	0.029*
C7	0.58549 (7)	0.92080 (16)	0.46957 (5)	0.0219 (3)
H7	0.5755	1.0148	0.4902	0.026*
C8	0.60507 (7)	0.77995 (15)	0.49740 (5)	0.0183 (3)
C9	0.62271 (7)	0.63717 (15)	0.46689 (5)	0.0173 (3)
C10	0.61666 (7)	0.64945 (16)	0.40782 (5)	0.0192 (3)
C11	0.65558 (7)	0.44683 (15)	0.55012 (5)	0.0182 (3)
C12	0.71645 (7)	0.51380 (15)	0.58382 (5)	0.0199 (3)
H12	0.7517	0.5876	0.5687	0.024*
C13	0.72607 (7)	0.47384 (16)	0.63911 (5)	0.0220 (3)
H13	0.7670	0.5212	0.6620	0.026*
C14	0.67492 (8)	0.36320 (16)	0.66076 (5)	0.0226 (3)
C15	0.61429 (8)	0.29422 (16)	0.62760 (6)	0.0235 (3)
H15	0.5795	0.2194	0.6427	0.028*
C16	0.60519 (8)	0.33568 (16)	0.57243 (5)	0.0222 (3)
H16	0.5643	0.2880	0.5496	0.027*
C81	0.60545 (7)	0.78930 (15)	0.55880 (5)	0.0180 (3)
C82	0.66047 (8)	0.88695 (16)	0.58767 (5)	0.0213 (3)
H82	0.6978	0.9448	0.5682	0.026*
C83	0.66135 (8)	0.90069 (16)	0.64442 (5)	0.0227 (3)
H83	0.6997	0.9656	0.6638	0.027*
C84	0.60552 (8)	0.81858 (17)	0.67278 (5)	0.0227 (3)
C85	0.54901 (7)	0.72304 (17)	0.64435 (5)	0.0228 (3)
H85	0.5106	0.6680	0.6637	0.027*
C86	0.54928 (7)	0.70913 (16)	0.58781 (5)	0.0201 (3)
H86	0.5108	0.6443	0.5685	0.024*
C141	0.68499 (8)	0.31483 (19)	0.71759 (6)	0.0287 (3)
C841	0.60570 (8)	0.83269 (19)	0.73182 (6)	0.0297 (3)

	U11	U22	U33	U12	U13	U23
N14	0.0462 (8)	0.0557 (10)	0.0262 (7)	−0.0037 (7)	0.0020 (6)	0.0074 (6)
N84	0.0411 (8)	0.0708 (11)	0.0227 (7)	−0.0121 (7)	0.0020 (6)	0.0000 (7)
C1	0.0156 (5)	0.0202 (6)	0.0184 (6)	−0.0023 (5)	−0.0006 (4)	−0.0009 (5)
C2	0.0210 (6)	0.0199 (7)	0.0239 (7)	0.0000 (5)	0.0007 (5)	−0.0011 (5)
C3	0.0229 (6)	0.0258 (7)	0.0227 (7)	−0.0014 (5)	0.0042 (5)	−0.0083 (5)
C4	0.0214 (6)	0.0298 (7)	0.0173 (6)	−0.0028 (5)	0.0018 (5)	−0.0033 (5)
C5	0.0210 (6)	0.0294 (7)	0.0169 (6)	−0.0014 (5)	0.0001 (5)	0.0039 (5)
C6	0.0216 (6)	0.0244 (7)	0.0253 (7)	0.0025 (5)	0.0020 (5)	0.0061 (5)
C7	0.0202 (6)	0.0210 (7)	0.0247 (7)	0.0007 (5)	0.0036 (5)	−0.0012 (5)
C8	0.0157 (5)	0.0221 (7)	0.0171 (6)	−0.0008 (5)	0.0023 (4)	−0.0016 (5)
C9	0.0142 (5)	0.0215 (6)	0.0161 (6)	−0.0009 (4)	0.0004 (4)	−0.0008 (5)
C10	0.0155 (5)	0.0248 (7)	0.0173 (6)	−0.0027 (5)	0.0013 (4)	−0.0001 (5)
C11	0.0188 (6)	0.0175 (6)	0.0182 (6)	0.0033 (5)	0.0014 (4)	−0.0010 (5)
C12	0.0182 (6)	0.0204 (6)	0.0209 (6)	0.0007 (5)	0.0006 (5)	0.0011 (5)
C13	0.0202 (6)	0.0240 (7)	0.0211 (6)	0.0016 (5)	−0.0025 (5)	−0.0017 (5)
C14	0.0256 (6)	0.0235 (7)	0.0188 (6)	0.0043 (5)	0.0021 (5)	0.0009 (5)
C15	0.0244 (6)	0.0213 (7)	0.0249 (7)	−0.0006 (5)	0.0033 (5)	0.0032 (5)
C16	0.0213 (6)	0.0207 (7)	0.0241 (7)	−0.0026 (5)	−0.0006 (5)	−0.0007 (5)
C81	0.0193 (6)	0.0170 (6)	0.0179 (6)	0.0034 (5)	0.0023 (4)	−0.0013 (5)
C82	0.0235 (6)	0.0202 (6)	0.0206 (6)	−0.0011 (5)	0.0033 (5)	0.0001 (5)
C83	0.0247 (6)	0.0213 (7)	0.0217 (6)	−0.0016 (5)	−0.0009 (5)	−0.0022 (5)
C84	0.0250 (6)	0.0253 (7)	0.0179 (6)	0.0026 (5)	0.0022 (5)	0.0008 (5)
C85	0.0202 (6)	0.0264 (7)	0.0222 (6)	0.0006 (5)	0.0041 (5)	0.0017 (5)
C86	0.0179 (6)	0.0214 (7)	0.0212 (6)	−0.0001 (5)	0.0020 (5)	−0.0025 (5)
C141	0.0290 (7)	0.0336 (8)	0.0235 (7)	−0.0007 (6)	0.0019 (5)	0.0020 (6)
C841	0.0277 (7)	0.0384 (9)	0.0229 (7)	−0.0045 (6)	0.0011 (5)	0.0005 (6)

N14—C141	1.1499 (19)	C11—C12	1.3971 (17)
N84—C841	1.1496 (19)	C12—C13	1.3867 (17)
C1—C2	1.3785 (18)	C12—H12	0.9500
C1—C9	1.4405 (17)	C13—C14	1.3951 (19)
C1—C11	1.4943 (17)	C13—H13	0.9500
C2—C3	1.4088 (18)	C14—C15	1.3938 (18)
C2—H2	0.9500	C14—C141	1.4411 (18)
C3—C4	1.3614 (19)	C15—C16	1.3864 (18)
C3—H3	0.9500	C15—H15	0.9500
C4—C10	1.4176 (18)	C16—H16	0.9500
C4—H4	0.9500	C81—C82	1.3957 (17)
C5—C6	1.3603 (19)	C81—C86	1.3976 (18)
C5—C10	1.4185 (18)	C82—C83	1.3864 (18)
C5—H5	0.9500	C82—H82	0.9500
C6—C7	1.4085 (18)	C83—C84	1.3926 (19)
C6—H6	0.9500	C83—H83	0.9500
C7—C8	1.3814 (18)	C84—C85	1.3973 (18)
C7—H7	0.9500	C84—C841	1.4431 (18)
C8—C9	1.4413 (17)	C85—C86	1.3829 (18)
C8—C81	1.4977 (17)	C85—H85	0.9500
C9—C10	1.4396 (17)	C86—H86	0.9500
C11—C16	1.3965 (18)
C2—C1—C9	119.88 (11)	C13—C12—H12	119.6
C2—C1—C11	115.18 (11)	C11—C12—H12	119.6
C9—C1—C11	124.93 (11)	C12—C13—C14	119.19 (12)
C1—C2—C3	122.46 (12)	C12—C13—H13	120.4
C1—C2—H2	118.8	C14—C13—H13	120.4
C3—C2—H2	118.8	C15—C14—C13	120.76 (12)
C4—C3—C2	119.08 (12)	C15—C14—C141	118.65 (13)
C4—C3—H3	120.5	C13—C14—C141	120.58 (12)
C2—C3—H3	120.5	C16—C15—C14	119.44 (12)
C3—C4—C10	121.23 (12)	C16—C15—H15	120.3
C3—C4—H4	119.4	C14—C15—H15	120.3
C10—C4—H4	119.4	C15—C16—C11	120.60 (12)
C6—C5—C10	120.96 (12)	C15—C16—H16	119.7
C6—C5—H5	119.5	C11—C16—H16	119.7
C10—C5—H5	119.5	C82—C81—C86	118.93 (11)
C5—C6—C7	119.30 (12)	C82—C81—C8	119.46 (11)
C5—C6—H6	120.4	C86—C81—C8	121.52 (11)
C7—C6—H6	120.4	C83—C82—C81	120.86 (12)
C8—C7—C6	122.49 (12)	C83—C82—H82	119.6
C8—C7—H7	118.8	C81—C82—H82	119.6
C6—C7—H7	118.8	C82—C83—C84	119.47 (12)
C7—C8—C9	119.65 (11)	C82—C83—H83	120.3
C7—C8—C81	115.56 (11)	C84—C83—H83	120.3
C9—C8—C81	124.79 (11)	C83—C84—C85	120.37 (12)
C10—C9—C1	116.95 (11)	C83—C84—C841	119.90 (12)
C10—C9—C8	116.99 (11)	C85—C84—C841	119.73 (12)
C1—C9—C8	126.06 (11)	C86—C85—C84	119.56 (12)
C4—C10—C5	119.01 (12)	C86—C85—H85	120.2
C4—C10—C9	120.40 (12)	C84—C85—H85	120.2
C5—C10—C9	120.59 (12)	C85—C86—C81	120.79 (12)
C16—C11—C12	119.22 (12)	C85—C86—H86	119.6
C16—C11—C1	119.01 (11)	C81—C86—H86	119.6
C12—C11—C1	121.67 (11)	N14—C141—C14	177.90 (17)
C13—C12—C11	120.78 (12)	N84—C841—C84	179.27 (18)
C9—C1—C2—C3	0.44 (19)	C2—C1—C11—C12	111.39 (14)
C11—C1—C2—C3	179.92 (11)	C9—C1—C11—C12	−69.16 (16)
C1—C2—C3—C4	−0.18 (19)	C16—C11—C12—C13	−1.45 (19)
C2—C3—C4—C10	0.18 (19)	C1—C11—C12—C13	−177.65 (12)
C10—C5—C6—C7	−0.33 (19)	C11—C12—C13—C14	1.13 (19)
C5—C6—C7—C8	−0.80 (19)	C12—C13—C14—C15	−0.6 (2)
C6—C7—C8—C9	1.79 (19)	C12—C13—C14—C141	177.82 (13)
C6—C7—C8—C81	−177.71 (11)	C13—C14—C15—C16	0.4 (2)
C2—C1—C9—C10	−0.67 (17)	C141—C14—C15—C16	−178.07 (13)
C11—C1—C9—C10	179.91 (11)	C14—C15—C16—C11	−0.7 (2)
C2—C1—C9—C8	179.44 (12)	C12—C11—C16—C15	1.22 (19)
C11—C1—C9—C8	0.02 (19)	C1—C11—C16—C15	177.52 (12)
C7—C8—C9—C10	−1.62 (17)	C7—C8—C81—C82	−65.72 (15)
C81—C8—C9—C10	177.84 (11)	C9—C8—C81—C82	114.80 (14)
C7—C8—C9—C1	178.27 (11)	C7—C8—C81—C86	110.83 (14)
C81—C8—C9—C1	−2.27 (19)	C9—C8—C81—C86	−68.65 (16)
C3—C4—C10—C5	179.57 (12)	C86—C81—C82—C83	2.07 (19)
C3—C4—C10—C9	−0.45 (19)	C8—C81—C82—C83	178.71 (12)
C6—C5—C10—C4	−179.61 (12)	C81—C82—C83—C84	−1.37 (19)
C6—C5—C10—C9	0.41 (19)	C82—C83—C84—C85	0.0 (2)
C1—C9—C10—C4	0.68 (16)	C82—C83—C84—C841	−179.70 (13)
C8—C9—C10—C4	−179.42 (11)	C83—C84—C85—C86	0.64 (19)
C1—C9—C10—C5	−179.34 (11)	C841—C84—C85—C86	−179.66 (12)
C8—C9—C10—C5	0.56 (17)	C84—C85—C86—C81	0.08 (19)
C2—C1—C11—C16	−64.81 (15)	C82—C81—C86—C85	−1.42 (18)
C9—C1—C11—C16	114.64 (14)	C8—C81—C86—C85	−177.98 (11)

Cg1and Cg2 are the centroids of the C1–C10 and C8–C10 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···Cg2i	0.95	2.75	3.6147 (13)	152
C16—H16···Cg2ii	0.95	2.92	3.6539 (15)	135
C82—H82···Cg1i	0.95	2.83	3.6180 (15)	141
C86—H86···Cg1ii	0.95	2.83	3.6614 (13)	147

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C10 and C8–C10 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯Cg2i	0.95	2.75	3.6147 (13)	152
C16—H16⋯Cg2ii	0.95	2.92	3.6539 (15)	135
C82—H82⋯Cg1i	0.95	2.83	3.6180 (15)	141
C86—H86⋯Cg1ii	0.95	2.83	3.6614 (13)	147

Symmetry codes: (i) ; (ii) .