9-(Pent-4-en-yl)anthracene.

In the title compound, C(19)H(18), the anthracene system is almost planar, with a maximum deviation of -0.039 (1) Å. The structure is stabilized by C-H⋯π inter-actions. The pentene moiety is not planar and is twisted away from the attached anthracene system with a maximum torsion angle of 91.2 (1)°.

Related literature

For background to anthracene, see: de Silva et al. (1997 ▶); Klarner et al. (1998 ▶); Han et al. (2009 ▶).

Experimental

Crystal data

C19H18

M = 246.33

Monoclinic,

a = 11.1555 (2) Å

b = 7.2678 (1) Å

c = 19.7129 (3) Å

β = 119.096 (1)°

V = 1396.55 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 100 K

0.73 × 0.38 × 0.26 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.953, T max = 0.983

20185 measured reflections

5271 independent reflections

3948 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.151

S = 1.05

5271 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.23 e Å−3

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

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811030571/ng5202sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811030571/ng5202Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811030571/ng5202Isup3.cml

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

C19H18	F(000) = 528
Mr = 246.33	Dx = 1.172 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5794 reflections
a = 11.1555 (2) Å	θ = 2.4–33.0°
b = 7.2678 (1) Å	µ = 0.07 mm−1
c = 19.7129 (3) Å	T = 100 K
β = 119.096 (1)°	Block, colourless
V = 1396.55 (4) Å3	0.73 × 0.38 × 0.26 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	5271 independent reflections
Radiation source: fine-focus sealed tube	3948 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 33.1°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −17→16
Tmin = 0.953, Tmax = 0.983	k = −9→11
20185 measured reflections	l = −30→30

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0816P)2 + 0.1778P] where P = (Fo2 + 2Fc2)/3
5271 reflections	(Δ/σ)max = 0.001
172 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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	0.12149 (8)	0.51562 (11)	0.87949 (5)	0.01455 (16)
C2	0.03754 (9)	0.45215 (12)	0.91135 (5)	0.01904 (17)
H2A	0.0693	0.3540	0.9478	0.023*
C3	−0.08723 (9)	0.53006 (14)	0.89033 (5)	0.02260 (19)
H3A	−0.1405	0.4860	0.9126	0.027*
C4	−0.13826 (9)	0.67610 (14)	0.83556 (6)	0.02333 (19)
H4A	−0.2250	0.7294	0.8216	0.028*
C5	−0.06301 (9)	0.73990 (12)	0.80296 (5)	0.01996 (18)
H5A	−0.0981	0.8372	0.7662	0.024*
C6	0.06813 (8)	0.66222 (11)	0.82341 (5)	0.01545 (16)
C7	0.14534 (8)	0.72875 (11)	0.79022 (5)	0.01635 (16)
H7A	0.1101	0.8263	0.7536	0.020*
C8	0.27345 (8)	0.65400 (11)	0.81012 (5)	0.01535 (16)
C9	0.35206 (9)	0.72202 (13)	0.77582 (5)	0.02136 (18)
H9A	0.3178	0.8221	0.7404	0.026*
C10	0.47518 (9)	0.64570 (14)	0.79301 (6)	0.0248 (2)
H10A	0.5258	0.6919	0.7695	0.030*
C11	0.52754 (9)	0.49685 (14)	0.84623 (6)	0.02274 (19)
H11A	0.6129	0.4430	0.8575	0.027*
C12	0.45707 (8)	0.43008 (12)	0.88137 (5)	0.01865 (17)
H12A	0.4948	0.3312	0.9172	0.022*
C13	0.32723 (8)	0.50604 (11)	0.86544 (5)	0.01458 (15)
C14	0.25201 (8)	0.43960 (11)	0.90096 (5)	0.01431 (15)
C15	0.30778 (9)	0.28354 (11)	0.95877 (5)	0.01744 (17)
H15A	0.2711	0.2941	0.9953	0.021*
H15B	0.4089	0.2943	0.9891	0.021*
C16	0.27031 (9)	0.09379 (11)	0.91969 (5)	0.01856 (17)
H16A	0.3180	0.0757	0.8890	0.022*
H16B	0.1703	0.0887	0.8836	0.022*
C17	0.31046 (9)	−0.06170 (12)	0.97964 (5)	0.01997 (18)
H17A	0.3154	−0.1789	0.9555	0.024*
H17B	0.4028	−0.0361	1.0238	0.024*
C18	0.21099 (11)	−0.08229 (13)	1.00944 (6)	0.0254 (2)
H18A	0.1204	−0.1198	0.9734	0.031*
C19	0.23850 (14)	−0.05277 (16)	1.08162 (7)	0.0363 (3)
H19A	0.3279	−0.0151	1.1195	0.044*
H19C	0.1689	−0.0692	1.0957	0.044*

	U11	U22	U33	U12	U13	U23
C1	0.0157 (3)	0.0131 (3)	0.0142 (3)	−0.0012 (2)	0.0068 (3)	−0.0018 (3)
C2	0.0204 (4)	0.0205 (4)	0.0175 (4)	−0.0032 (3)	0.0101 (3)	−0.0017 (3)
C3	0.0200 (4)	0.0287 (4)	0.0226 (4)	−0.0048 (3)	0.0131 (3)	−0.0049 (4)
C4	0.0156 (4)	0.0283 (4)	0.0260 (4)	0.0005 (3)	0.0100 (3)	−0.0056 (4)
C5	0.0165 (3)	0.0199 (4)	0.0207 (4)	0.0034 (3)	0.0069 (3)	−0.0005 (3)
C6	0.0146 (3)	0.0147 (3)	0.0157 (3)	0.0005 (3)	0.0063 (3)	−0.0014 (3)
C7	0.0170 (3)	0.0144 (3)	0.0164 (4)	0.0015 (3)	0.0071 (3)	0.0018 (3)
C8	0.0159 (3)	0.0150 (3)	0.0151 (3)	−0.0003 (3)	0.0075 (3)	0.0001 (3)
C9	0.0208 (4)	0.0235 (4)	0.0215 (4)	−0.0012 (3)	0.0116 (3)	0.0027 (3)
C10	0.0209 (4)	0.0321 (5)	0.0253 (4)	−0.0029 (3)	0.0144 (4)	0.0003 (4)
C11	0.0165 (4)	0.0276 (4)	0.0245 (4)	0.0010 (3)	0.0103 (3)	−0.0046 (4)
C12	0.0162 (3)	0.0173 (4)	0.0203 (4)	0.0020 (3)	0.0071 (3)	−0.0017 (3)
C13	0.0141 (3)	0.0132 (3)	0.0152 (3)	0.0003 (2)	0.0061 (3)	−0.0022 (3)
C14	0.0159 (3)	0.0115 (3)	0.0139 (3)	0.0000 (2)	0.0060 (3)	−0.0008 (3)
C15	0.0201 (4)	0.0139 (3)	0.0155 (3)	0.0004 (3)	0.0065 (3)	0.0009 (3)
C16	0.0220 (4)	0.0140 (3)	0.0171 (4)	0.0002 (3)	0.0074 (3)	0.0004 (3)
C17	0.0230 (4)	0.0135 (3)	0.0200 (4)	0.0013 (3)	0.0078 (3)	0.0019 (3)
C18	0.0320 (5)	0.0180 (4)	0.0272 (5)	−0.0009 (3)	0.0151 (4)	0.0021 (3)
C19	0.0531 (7)	0.0295 (5)	0.0336 (6)	0.0003 (5)	0.0267 (5)	0.0015 (5)

C1—C14	1.4159 (11)	C11—C12	1.3650 (13)
C1—C2	1.4340 (11)	C11—H11A	0.9500
C1—C6	1.4393 (11)	C12—C13	1.4349 (11)
C2—C3	1.3670 (12)	C12—H12A	0.9500
C2—H2A	0.9500	C13—C14	1.4139 (11)
C3—C4	1.4208 (14)	C14—C15	1.5108 (11)
C3—H3A	0.9500	C15—C16	1.5352 (11)
C4—C5	1.3628 (13)	C15—H15A	0.9900
C4—H4A	0.9500	C15—H15B	0.9900
C5—C6	1.4311 (11)	C16—C17	1.5361 (12)
C5—H5A	0.9500	C16—H16A	0.9900
C6—C7	1.3971 (12)	C16—H16B	0.9900
C7—C8	1.3950 (11)	C17—C18	1.4941 (14)
C7—H7A	0.9500	C17—H17A	0.9900
C8—C9	1.4309 (12)	C17—H17B	0.9900
C8—C13	1.4385 (11)	C18—C19	1.3193 (15)
C9—C10	1.3625 (13)	C18—H18A	0.9500
C9—H9A	0.9500	C19—H19A	0.9500
C10—C11	1.4199 (14)	C19—H19C	0.9500
C10—H10A	0.9500
C14—C1—C2	122.63 (7)	C11—C12—C13	121.42 (8)
C14—C1—C6	119.97 (7)	C11—C12—H12A	119.3
C2—C1—C6	117.40 (7)	C13—C12—H12A	119.3
C3—C2—C1	121.30 (8)	C14—C13—C12	122.63 (7)
C3—C2—H2A	119.3	C14—C13—C8	120.10 (7)
C1—C2—H2A	119.3	C12—C13—C8	117.26 (7)
C2—C3—C4	120.83 (8)	C13—C14—C1	119.36 (7)
C2—C3—H3A	119.6	C13—C14—C15	120.27 (7)
C4—C3—H3A	119.6	C1—C14—C15	120.32 (7)
C5—C4—C3	120.09 (8)	C14—C15—C16	112.59 (7)
C5—C4—H4A	120.0	C14—C15—H15A	109.1
C3—C4—H4A	120.0	C16—C15—H15A	109.1
C4—C5—C6	120.84 (8)	C14—C15—H15B	109.1
C4—C5—H5A	119.6	C16—C15—H15B	109.1
C6—C5—H5A	119.6	H15A—C15—H15B	107.8
C7—C6—C5	120.67 (8)	C15—C16—C17	111.62 (7)
C7—C6—C1	119.80 (7)	C15—C16—H16A	109.3
C5—C6—C1	119.52 (8)	C17—C16—H16A	109.3
C8—C7—C6	120.93 (7)	C15—C16—H16B	109.3
C8—C7—H7A	119.5	C17—C16—H16B	109.3
C6—C7—H7A	119.5	H16A—C16—H16B	108.0
C7—C8—C9	120.79 (8)	C18—C17—C16	112.44 (7)
C7—C8—C13	119.79 (7)	C18—C17—H17A	109.1
C9—C8—C13	119.41 (7)	C16—C17—H17A	109.1
C10—C9—C8	121.14 (8)	C18—C17—H17B	109.1
C10—C9—H9A	119.4	C16—C17—H17B	109.1
C8—C9—H9A	119.4	H17A—C17—H17B	107.8
C9—C10—C11	119.78 (8)	C19—C18—C17	125.45 (10)
C9—C10—H10A	120.1	C19—C18—H18A	117.3
C11—C10—H10A	120.1	C17—C18—H18A	117.3
C12—C11—C10	120.96 (8)	C18—C19—H19A	120.0
C12—C11—H11A	119.5	C18—C19—H19C	120.0
C10—C11—H11A	119.5	H19A—C19—H19C	120.0
C14—C1—C2—C3	179.04 (8)	C11—C12—C13—C14	179.98 (8)
C6—C1—C2—C3	−1.14 (12)	C11—C12—C13—C8	0.79 (12)
C1—C2—C3—C4	0.48 (14)	C7—C8—C13—C14	−1.54 (12)
C2—C3—C4—C5	0.28 (14)	C9—C8—C13—C14	178.80 (8)
C3—C4—C5—C6	−0.31 (14)	C7—C8—C13—C12	177.67 (7)
C4—C5—C6—C7	−179.61 (8)	C9—C8—C13—C12	−1.98 (11)
C4—C5—C6—C1	−0.39 (13)	C12—C13—C14—C1	−176.95 (7)
C14—C1—C6—C7	0.14 (12)	C8—C13—C14—C1	2.22 (12)
C2—C1—C6—C7	−179.68 (7)	C12—C13—C14—C15	0.50 (12)
C14—C1—C6—C5	−179.09 (7)	C8—C13—C14—C15	179.67 (7)
C2—C1—C6—C5	1.09 (12)	C2—C1—C14—C13	178.29 (7)
C5—C6—C7—C8	179.78 (8)	C6—C1—C14—C13	−1.52 (12)
C1—C6—C7—C8	0.56 (12)	C2—C1—C14—C15	0.84 (12)
C6—C7—C8—C9	179.78 (8)	C6—C1—C14—C15	−178.97 (7)
C6—C7—C8—C13	0.13 (12)	C13—C14—C15—C16	−86.19 (9)
C7—C8—C9—C10	−177.80 (8)	C1—C14—C15—C16	91.23 (9)
C13—C8—C9—C10	1.85 (13)	C14—C15—C16—C17	−172.08 (7)
C8—C9—C10—C11	−0.43 (14)	C15—C16—C17—C18	78.26 (9)
C9—C10—C11—C12	−0.83 (15)	C16—C17—C18—C19	−114.87 (11)
C10—C11—C12—C13	0.63 (14)

Cg1 and Cg2 are the centroids of the C1–C6 and C1/C6–C8/C13/C14 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···Cg2i	0.95	2.63	3.5729 (9)	175
C7—H7A···Cg1i	0.95	2.74	3.6851 (9)	177
C17—H17A···Cg2ii	0.99	2.58	3.4643 (9)	149
C18—H18A···Cg1ii	0.95	2.90	3.6553 (11)	138

Table 1

C—H⋯π interactions (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C1/C6–C8/C13/C14 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯Cg2i	0.95	2.63	3.5729 (9)	175
C7—H7A⋯Cg1i	0.95	2.74	3.6851 (9)	177
C17—H17A⋯Cg2ii	0.99	2.58	3.4643 (9)	149
C18—H18A⋯Cg1ii	0.95	2.90	3.6553 (11)	138

Symmetry codes: (i) ; (ii) .