1,3-Bis(propan-2-yl)naphthalene.

In the title compound, C(16)H(20), one of the isopropyl groups shows almost equal displacements [1.252 (1) and -1.270 (1) Å] of its methyl-C atoms from the mean plane of the naphthalene ring system, while the other shows asymmetric displacements [1.586 (2) and -0.315 (1) Å]. In the crystal, the mol-ecules are linked into sheets lying in the ab plane by three C-H⋯π contacts, two involving donors belonging to the isopropyl groups and the third a donor atom from the naphthalene ring system. The different orientations of the isopropyl groups might be attributed to the fact that the C-H⋯π inter-action involving one of them is enhanced by the C-H⋯π inter-action involving the aromatic ring.

Related literature

For background to diisopropyl­naphthalenes, see: Addison (1983 ▶); Brzozowski et al. (2001 ▶); Collin et al. (2003 ▶).

Experimental

Crystal data

C16H20

M = 212.32

Orthorhombic,

a = 16.1044 (12) Å

b = 8.2099 (5) Å

c = 19.0303 (13) Å

V = 2516.1 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.06 mm−1

T = 150 K

0.22 × 0.20 × 0.04 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.986, T max = 0.998

12847 measured reflections

2751 independent reflections

2240 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.108

S = 1.04

2751 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.21 e Å−3

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

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811047854/hb6496sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811047854/hb6496Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811047854/hb6496Isup3.cml

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

C16H20	Dx = 1.121 Mg m−3
Mr = 212.32	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 421 reflections
a = 16.1044 (12) Å	θ = 3.9–23.6°
b = 8.2099 (5) Å	µ = 0.06 mm−1
c = 19.0303 (13) Å	T = 150 K
V = 2516.1 (3) Å3	Block, colourless
Z = 8	0.22 × 0.20 × 0.04 mm
F(000) = 928

Bruker SMART APEX CCD diffractometer	2751 independent reflections
Radiation source: fine-focus sealed tube	2240 reflections with I > 2σ(I)
graphite	Rint = 0.036
ω scans	θmax = 27.1°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −12→20
Tmin = 0.986, Tmax = 0.998	k = −10→8
12847 measured reflections	l = −24→18

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0398P)2 + 0.9272P] where P = (Fo2 + 2Fc2)/3
2751 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.21 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
C1	0.35224 (7)	0.39257 (16)	0.18964 (7)	0.0211 (3)
C11	0.30803 (7)	0.23796 (16)	0.16559 (7)	0.0230 (3)
H11	0.2519	0.2366	0.1881	0.028*
C111	0.29530 (9)	0.22710 (18)	0.08610 (7)	0.0321 (3)
H11A	0.2666	0.1252	0.0746	0.048*
H11B	0.3494	0.2295	0.0625	0.048*
H11C	0.2617	0.3196	0.0702	0.048*
C112	0.35537 (8)	0.08727 (17)	0.19147 (8)	0.0288 (3)
H11D	0.3266	−0.0114	0.1758	0.043*
H11E	0.3580	0.0885	0.2429	0.043*
H11F	0.4118	0.0884	0.1722	0.043*
C2	0.40246 (7)	0.47957 (16)	0.14496 (7)	0.0223 (3)
H2	0.4066	0.4450	0.0974	0.027*
C3	0.44854 (7)	0.61884 (15)	0.16637 (7)	0.0221 (3)
C31	0.50394 (8)	0.70740 (16)	0.11426 (7)	0.0250 (3)
H31	0.5322	0.7979	0.1400	0.030*
C311	0.45361 (9)	0.78327 (18)	0.05444 (8)	0.0332 (3)
H31A	0.4912	0.8394	0.0220	0.050*
H31B	0.4138	0.8616	0.0738	0.050*
H31C	0.4236	0.6975	0.0292	0.050*
C312	0.57143 (8)	0.59413 (18)	0.08548 (8)	0.0314 (3)
H31D	0.6061	0.6539	0.0519	0.047*
H31E	0.5454	0.5013	0.0618	0.047*
H31F	0.6060	0.5548	0.1243	0.047*
C4	0.44313 (7)	0.66789 (16)	0.23492 (7)	0.0225 (3)
H4	0.4738	0.7604	0.2500	0.027*
C5	0.38868 (8)	0.63261 (16)	0.35543 (7)	0.0257 (3)
H5	0.4211	0.7224	0.3708	0.031*
C6	0.33889 (8)	0.55295 (18)	0.40250 (7)	0.0283 (3)
H6	0.3372	0.5871	0.4502	0.034*
C7	0.29021 (8)	0.42038 (17)	0.38021 (7)	0.0274 (3)
H7	0.2546	0.3671	0.4127	0.033*
C8	0.29370 (8)	0.36748 (17)	0.31199 (7)	0.0245 (3)
H8	0.2609	0.2769	0.2981	0.029*
C9	0.34551 (7)	0.44543 (16)	0.26157 (7)	0.0211 (3)
C10	0.39261 (7)	0.58325 (16)	0.28397 (7)	0.0216 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0173 (6)	0.0207 (6)	0.0253 (7)	0.0017 (5)	−0.0029 (5)	−0.0020 (5)
C11	0.0196 (6)	0.0224 (7)	0.0270 (7)	−0.0032 (5)	0.0008 (5)	−0.0018 (6)
C111	0.0374 (8)	0.0291 (8)	0.0297 (8)	−0.0099 (6)	−0.0043 (6)	−0.0038 (6)
C112	0.0272 (7)	0.0230 (7)	0.0360 (8)	−0.0018 (6)	−0.0002 (6)	−0.0029 (6)
C2	0.0211 (6)	0.0224 (7)	0.0232 (6)	0.0006 (5)	−0.0012 (5)	−0.0023 (6)
C3	0.0198 (6)	0.0203 (7)	0.0261 (7)	0.0007 (5)	−0.0028 (5)	0.0000 (5)
C31	0.0275 (6)	0.0212 (7)	0.0261 (7)	−0.0054 (5)	−0.0002 (5)	−0.0001 (6)
C311	0.0401 (8)	0.0279 (8)	0.0317 (8)	0.0006 (6)	−0.0002 (6)	0.0036 (6)
C312	0.0277 (7)	0.0324 (8)	0.0342 (8)	−0.0036 (6)	0.0050 (6)	−0.0010 (7)
C4	0.0204 (6)	0.0191 (6)	0.0280 (7)	−0.0004 (5)	−0.0041 (5)	−0.0030 (5)
C5	0.0250 (6)	0.0243 (7)	0.0280 (7)	0.0024 (5)	−0.0045 (5)	−0.0052 (6)
C6	0.0276 (7)	0.0324 (8)	0.0248 (7)	0.0061 (6)	−0.0003 (5)	−0.0050 (6)
C7	0.0230 (6)	0.0314 (8)	0.0279 (7)	0.0023 (6)	0.0032 (5)	0.0015 (6)
C8	0.0193 (6)	0.0257 (7)	0.0285 (7)	−0.0005 (5)	−0.0005 (5)	−0.0017 (6)
C9	0.0164 (6)	0.0212 (6)	0.0257 (7)	0.0035 (5)	−0.0020 (5)	−0.0012 (5)
C10	0.0182 (6)	0.0211 (7)	0.0253 (7)	0.0042 (5)	−0.0035 (5)	−0.0024 (5)

C1—C2	1.3738 (18)	C311—H31A	0.9800
C1—C9	1.4400 (18)	C311—H31B	0.9800
C1—C11	1.5256 (18)	C311—H31C	0.9800
C11—C111	1.5291 (19)	C312—H31D	0.9800
C11—C112	1.5344 (19)	C312—H31E	0.9800
C11—H11	1.0000	C312—H31F	0.9800
C111—H11A	0.9800	C4—C10	1.4199 (18)
C111—H11B	0.9800	C4—H4	0.9500
C111—H11C	0.9800	C5—C6	1.369 (2)
C112—H11D	0.9800	C5—C10	1.4203 (18)
C112—H11E	0.9800	C5—H5	0.9500
C112—H11F	0.9800	C6—C7	1.407 (2)
C2—C3	1.4228 (17)	C6—H6	0.9500
C2—H2	0.9500	C7—C8	1.3701 (19)
C3—C4	1.3680 (18)	C7—H7	0.9500
C3—C31	1.5193 (18)	C8—C9	1.4236 (18)
C31—C311	1.5299 (19)	C8—H8	0.9500
C31—C312	1.5318 (19)	C9—C10	1.4273 (18)
C31—H31	1.0000
C2—C1—C9	118.42 (12)	C31—C311—H31A	109.5
C2—C1—C11	121.44 (12)	C31—C311—H31B	109.5
C9—C1—C11	120.05 (11)	H31A—C311—H31B	109.5
C1—C11—C111	114.07 (11)	C31—C311—H31C	109.5
C1—C11—C112	110.04 (10)	H31A—C311—H31C	109.5
C111—C11—C112	109.70 (11)	H31B—C311—H31C	109.5
C1—C11—H11	107.6	C31—C312—H31D	109.5
C111—C11—H11	107.6	C31—C312—H31E	109.5
C112—C11—H11	107.6	H31D—C312—H31E	109.5
C11—C111—H11A	109.5	C31—C312—H31F	109.5
C11—C111—H11B	109.5	H31D—C312—H31F	109.5
H11A—C111—H11B	109.5	H31E—C312—H31F	109.5
C11—C111—H11C	109.5	C3—C4—C10	121.29 (12)
H11A—C111—H11C	109.5	C3—C4—H4	119.4
H11B—C111—H11C	109.5	C10—C4—H4	119.4
C11—C112—H11D	109.5	C6—C5—C10	121.09 (13)
C11—C112—H11E	109.5	C6—C5—H5	119.5
H11D—C112—H11E	109.5	C10—C5—H5	119.5
C11—C112—H11F	109.5	C5—C6—C7	119.93 (13)
H11D—C112—H11F	109.5	C5—C6—H6	120.0
H11E—C112—H11F	109.5	C7—C6—H6	120.0
C1—C2—C3	123.20 (12)	C8—C7—C6	120.54 (13)
C1—C2—H2	118.4	C8—C7—H7	119.7
C3—C2—H2	118.4	C6—C7—H7	119.7
C4—C3—C2	118.45 (12)	C7—C8—C9	121.34 (13)
C4—C3—C31	121.27 (12)	C7—C8—H8	119.3
C2—C3—C31	120.26 (12)	C9—C8—H8	119.3
C3—C31—C311	111.68 (11)	C8—C9—C10	117.81 (12)
C3—C31—C312	111.07 (11)	C8—C9—C1	123.32 (12)
C311—C31—C312	110.93 (12)	C10—C9—C1	118.87 (11)
C3—C31—H31	107.7	C4—C10—C5	121.02 (12)
C311—C31—H31	107.7	C4—C10—C9	119.74 (12)
C312—C31—H31	107.7	C5—C10—C9	119.24 (12)
C2—C1—C11—C111	−23.24 (17)	C6—C7—C8—C9	−0.8 (2)
C9—C1—C11—C111	160.20 (12)	C7—C8—C9—C10	−1.32 (18)
C2—C1—C11—C112	100.54 (14)	C7—C8—C9—C1	178.96 (12)
C9—C1—C11—C112	−76.03 (14)	C2—C1—C9—C8	178.25 (12)
C9—C1—C2—C3	0.37 (18)	C11—C1—C9—C8	−5.08 (18)
C11—C1—C2—C3	−176.25 (11)	C2—C1—C9—C10	−1.47 (17)
C1—C2—C3—C4	0.52 (19)	C11—C1—C9—C10	175.20 (11)
C1—C2—C3—C31	179.01 (12)	C3—C4—C10—C5	178.59 (12)
C4—C3—C31—C311	−117.29 (14)	C3—C4—C10—C9	−0.82 (18)
C2—C3—C31—C311	64.27 (16)	C6—C5—C10—C4	178.83 (12)
C4—C3—C31—C312	118.31 (14)	C6—C5—C10—C9	−1.76 (19)
C2—C3—C31—C312	−60.14 (15)	C8—C9—C10—C4	−178.04 (11)
C2—C3—C4—C10	−0.29 (18)	C1—C9—C10—C4	1.70 (17)
C31—C3—C4—C10	−178.76 (11)	C8—C9—C10—C5	2.54 (17)
C10—C5—C6—C7	−0.3 (2)	C1—C9—C10—C5	−177.73 (11)
C5—C6—C7—C8	1.6 (2)

Cg1 and Cg2 are the centroids of the C1–C4/C9/C10 and C5–C10 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···Cg2i	0.95	2.88	3.7399 (15)	151
C11—H11···Cg1i	1.00	2.98	3.8289 (13)	144
C31—H31···Cg2ii	1.00	2.68	3.6048 (14)	155

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C4/C9/C10 and C5–C10 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯Cg2i	0.95	2.88	3.7399 (15)	151
C11—H11⋯Cg1i	1.00	2.98	3.8289 (13)	144
C31—H31⋯Cg2ii	1.00	2.68	3.6048 (14)	155

Symmetry codes: (i) ; (ii) .