(E)-Methyl 3-(10-bromo-anthracen-9-yl)acrylate.

In the title mol-ecule, C18H13BrO2, the anthracene unit forms an angle of 46.91 (2)° with the mean plane of the methyl acrylate moiety. In the crystal, the mol-ecules arrange themselves into strands parallel to [010] and, due to the crystal symmetry, there are eight strands crossing the unit cell. In each strand, mol-ecules form short C-H⋯O and C-H⋯π contacts and have their anthracene groups parallel to each other. Neighboring strands, related by a c-glide operation, are connected via C-H⋯O inter-actions and form a layer parallel to (100). The arrangement of the acrylate and anthracene groups in the crystal do not allow for [2 + 2] or [4 + 4] cyclo-addition.

Related literature

For an analogous preparation of the title compound, see: Bugenhagen et al. (2013 ▶); Nguyen & Weizman (2007 ▶). For crystal structures of photodimerizable aryl-enes, see: Vishnumurthy et al. (2002 ▶); Mascitti & Corey (2006 ▶); Sonoda (2011 ▶); Schmidt (1964 ▶). For the photodimerization of anthracenes in the crystal, see: Schmidt (1971 ▶); Ihmels et al. (2000 ▶). For the X-ray crystal structure of a non-planar bromo­anthracene, see: Barkhuizen et al. (2004 ▶).

Experimental

Crystal data

C18H13BrO2

M = 341.19

Orthorhombic,

a = 40.5848 (4) Å

b = 5.32093 (5) Å

c = 13.0710 (1) Å

V = 2822.67 (5) Å3

Z = 8

Cu Kα radiation

μ = 3.98 mm−1

T = 100 K

0.21 × 0.19 × 0.13 mm

Data collection

Oxford Diffraction SuperNova, Dual, Cu at zero, Atlas diffractometer

Absorption correction: analytical (CrysAlis PRO; Agilent, 2013 ▶) T min = 0.891, T max = 0.924

25313 measured reflections

2961 independent reflections

2900 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.066

S = 1.12

2961 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.44 e Å−3

Data collection: CrysAlis PRO (Agilent, 2013 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) within OLEX2 (Dolomanov et al., 2009 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813016905/gk2574sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813016905/gk2574Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813016905/gk2574Isup3.cml

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

C18H13BrO2	Dx = 1.606 Mg m−3
Mr = 341.19	Melting point: 425 K
Orthorhombic, Pbcn	Cu Kα radiation, λ = 1.5418 Å
a = 40.5848 (4) Å	Cell parameters from 13502 reflections
b = 5.32093 (5) Å	θ = 4.3–76.3°
c = 13.0710 (1) Å	µ = 3.98 mm−1
V = 2822.67 (5) Å3	T = 100 K
Z = 8	Block, light yellow
F(000) = 1376	0.21 × 0.19 × 0.13 mm

Oxford Diffraction SuperNova, Dual, Cu at zero, Atlas diffractometer	2961 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2900 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.022
Detector resolution: 10.4127 pixels mm-1	θmax = 76.3°, θmin = 4.4°
ω scans	h = −50→44
Absorption correction: analytical (CrysAlis PRO; Agilent, 2013)	k = −5→6
Tmin = 0.891, Tmax = 0.924	l = −15→16
25313 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.026	H-atom parameters constrained
wR(F2) = 0.066	w = 1/[σ2(Fo2) + (0.0253P)2 + 4.4132P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max = 0.003
2961 reflections	Δρmax = 0.31 e Å−3
191 parameters	Δρmin = −0.44 e Å−3
0 restraints

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.

	x	y	z	Uiso*/Ueq
Br1	0.28462 (2)	1.11853 (4)	0.77185 (2)	0.01637 (8)
C1	0.32116 (4)	0.9076 (3)	0.73973 (14)	0.0125 (4)
C10	0.34022 (5)	0.3729 (3)	0.56492 (14)	0.0143 (4)
C11	0.31165 (5)	0.3554 (4)	0.51014 (14)	0.0159 (4)
C12	0.28558 (4)	0.5263 (4)	0.52784 (14)	0.0157 (4)
C13	0.28813 (4)	0.7045 (4)	0.60248 (14)	0.0141 (4)
C14	0.31732 (4)	0.7266 (3)	0.66306 (13)	0.0121 (3)
C15	0.40212 (4)	0.4163 (3)	0.67191 (14)	0.0132 (4)
C16	0.43266 (4)	0.4937 (4)	0.65111 (14)	0.0145 (4)
C17	0.45923 (4)	0.3109 (4)	0.63028 (14)	0.0147 (4)
C18	0.51645 (5)	0.2672 (4)	0.60385 (19)	0.0263 (5)
C2	0.35047 (4)	0.9392 (3)	0.79499 (14)	0.0122 (3)
C3	0.35474 (5)	1.1300 (3)	0.87078 (14)	0.0144 (4)
C4	0.38315 (5)	1.1478 (4)	0.92569 (14)	0.0165 (4)
C5	0.40887 (4)	0.9717 (4)	0.91069 (14)	0.0160 (4)
C6	0.40616 (4)	0.7915 (4)	0.83732 (14)	0.0148 (4)
C7	0.37738 (4)	0.7705 (3)	0.77405 (13)	0.0119 (3)
C8	0.37435 (4)	0.5854 (3)	0.69716 (14)	0.0120 (3)
C9	0.34444 (4)	0.5594 (3)	0.64271 (14)	0.0120 (3)
H10	0.3573	0.2613	0.5514	0.017*
H11	0.3093	0.2304	0.4609	0.019*
H12	0.2666	0.5171	0.4883	0.019*
H13	0.2706	0.8133	0.6141	0.017*
H15	0.3980	0.2444	0.6704	0.016*
H16	0.4373	0.6648	0.6497	0.017*
H18A	0.5146	0.1947	0.5368	0.039*
H18B	0.5169	0.1357	0.6541	0.039*
H18C	0.5364	0.3639	0.6081	0.039*
H3	0.3378	1.2440	0.8828	0.017*
H4	0.3857	1.2763	0.9733	0.020*
H5	0.4277	0.9793	0.9512	0.019*
H6	0.4234	0.6788	0.8279	0.018*
O1	0.48841 (3)	0.4289 (3)	0.62263 (12)	0.0218 (3)
O2	0.45611 (3)	0.0860 (3)	0.62159 (11)	0.0188 (3)

	U11	U22	U33	U12	U13	U23
Br1	0.01322 (11)	0.01739 (12)	0.01851 (12)	0.00440 (7)	0.00145 (7)	−0.00092 (7)
C1	0.0115 (8)	0.0126 (8)	0.0134 (8)	0.0022 (7)	0.0032 (7)	0.0026 (7)
C10	0.0131 (8)	0.0149 (9)	0.0150 (8)	−0.0007 (7)	0.0037 (7)	−0.0002 (7)
C11	0.0174 (9)	0.0177 (9)	0.0126 (8)	−0.0038 (7)	0.0028 (7)	−0.0025 (7)
C12	0.0129 (8)	0.0203 (10)	0.0140 (9)	−0.0035 (7)	−0.0003 (7)	0.0027 (8)
C13	0.0115 (8)	0.0151 (9)	0.0155 (9)	0.0000 (7)	0.0014 (7)	0.0039 (8)
C14	0.0111 (8)	0.0130 (8)	0.0122 (8)	−0.0004 (7)	0.0020 (6)	0.0030 (7)
C15	0.0141 (8)	0.0119 (8)	0.0137 (8)	0.0019 (7)	−0.0009 (7)	−0.0001 (7)
C16	0.0145 (8)	0.0111 (8)	0.0180 (9)	0.0009 (7)	0.0015 (7)	0.0005 (7)
C17	0.0118 (8)	0.0175 (9)	0.0149 (8)	−0.0002 (7)	−0.0009 (7)	−0.0021 (7)
C18	0.0111 (9)	0.0307 (12)	0.0371 (12)	0.0045 (8)	0.0014 (8)	−0.0118 (10)
C2	0.0119 (8)	0.0121 (8)	0.0126 (8)	−0.0005 (7)	0.0024 (7)	0.0030 (7)
C3	0.0144 (8)	0.0137 (9)	0.0151 (9)	0.0008 (7)	0.0033 (7)	0.0000 (7)
C4	0.0189 (9)	0.0173 (9)	0.0134 (8)	−0.0037 (7)	0.0027 (7)	−0.0017 (7)
C5	0.0124 (8)	0.0207 (10)	0.0148 (8)	−0.0030 (7)	−0.0016 (7)	0.0015 (8)
C6	0.0117 (8)	0.0161 (9)	0.0167 (9)	0.0009 (7)	0.0005 (7)	0.0022 (7)
C7	0.0117 (8)	0.0113 (8)	0.0128 (8)	−0.0008 (7)	0.0019 (6)	0.0031 (7)
C8	0.0114 (8)	0.0109 (8)	0.0138 (8)	0.0005 (7)	0.0021 (7)	0.0032 (7)
C9	0.0119 (8)	0.0113 (8)	0.0128 (8)	−0.0009 (7)	0.0031 (6)	0.0011 (7)
O1	0.0098 (6)	0.0199 (7)	0.0356 (8)	−0.0004 (5)	0.0041 (6)	−0.0088 (6)
O2	0.0162 (6)	0.0136 (7)	0.0266 (7)	0.0024 (5)	0.0007 (6)	−0.0016 (6)

C1—Br1	1.9068 (18)	C18—H18C	0.9600
C1—C14	1.398 (3)	C18—H18B	0.9600
C1—C2	1.402 (3)	C18—H18A	0.9600
C10—C11	1.366 (3)	C2—C7	1.440 (2)
C10—H10	0.9300	C2—C3	1.429 (3)
C11—C12	1.414 (3)	C3—C4	1.361 (3)
C11—H11	0.9300	C3—H3	0.9300
C12—C13	1.364 (3)	C4—C5	1.416 (3)
C12—H12	0.9300	C4—H4	0.9300
C13—C14	1.430 (2)	C5—C6	1.361 (3)
C13—H13	0.9300	C5—H5	0.9300
C15—C16	1.334 (3)	C6—C7	1.435 (2)
C15—H15	0.9300	C6—H6	0.9300
C16—C17	1.478 (3)	C7—C8	1.413 (3)
C16—H16	0.9300	C8—C15	1.479 (2)
C17—O2	1.208 (2)	C8—C9	1.414 (2)
C17—O1	1.344 (2)	C9—C14	1.440 (2)
C18—O1	1.448 (2)	C9—C10	1.431 (3)
C2—C1—Br1	118.41 (14)	C11—C10—H10	119.3
C14—C1—C2	123.12 (17)	C10—C11—H11	119.8
C14—C1—Br1	118.46 (14)	C10—C11—C12	120.37 (18)
C1—C2—C3	123.06 (17)	C12—C11—H11	119.8
C1—C2—C7	118.09 (17)	C11—C12—H12	119.8
C3—C2—C7	118.85 (17)	C13—C12—C11	120.48 (17)
C2—C3—H3	119.4	C13—C12—H12	119.8
C4—C3—C2	121.20 (18)	C12—C13—H13	119.5
C4—C3—H3	119.4	C12—C13—C14	121.07 (17)
C3—C4—H4	119.8	C14—C13—H13	119.5
C3—C4—C5	120.32 (18)	C1—C14—C9	118.22 (16)
C5—C4—H4	119.8	C1—C14—C13	123.08 (17)
C4—C5—H5	119.9	C13—C14—C9	118.68 (17)
C6—C5—C4	120.29 (17)	C8—C15—H15	117.8
C6—C5—H5	119.9	C16—C15—C8	124.45 (17)
C5—C6—H6	119.1	C16—C15—H15	117.8
C5—C6—C7	121.77 (17)	C15—C16—H16	119.6
C7—C6—H6	119.1	C15—C16—C17	120.83 (18)
C6—C7—C2	117.34 (16)	C17—C16—H16	119.6
C8—C7—C2	120.27 (16)	O1—C17—C16	110.43 (17)
C8—C7—C6	122.32 (17)	O2—C17—C16	126.35 (18)
C7—C8—C9	120.06 (16)	O2—C17—O1	123.22 (18)
C7—C8—C15	121.10 (16)	H18A—C18—H18B	109.5
C9—C8—C15	118.84 (16)	H18A—C18—H18C	109.5
C8—C9—C10	121.88 (17)	H18B—C18—H18C	109.5
C8—C9—C14	120.18 (16)	O1—C18—H18A	109.5
C10—C9—C14	117.93 (16)	O1—C18—H18B	109.5
C9—C10—H10	119.3	O1—C18—H18C	109.5
C11—C10—C9	121.42 (18)	C17—O1—C18	115.31 (16)
C1—C2—C3—C4	177.29 (18)	C8—C15—C16—C17	177.77 (17)
C1—C2—C7—C6	−174.75 (17)	C9—C8—C15—C16	128.8 (2)
C1—C2—C7—C8	2.3 (3)	C9—C10—C11—C12	1.3 (3)
C2—C1—C14—C9	2.3 (3)	C10—C9—C14—C1	179.34 (16)
C2—C1—C14—C13	−176.07 (17)	C10—C9—C14—C13	−2.2 (3)
C2—C3—C4—C5	−1.8 (3)	C10—C11—C12—C13	−2.5 (3)
C2—C7—C8—C9	−2.1 (3)	C11—C12—C13—C14	1.3 (3)
C2—C7—C8—C15	177.76 (16)	C12—C13—C14—C1	179.44 (18)
C3—C2—C7—C6	5.1 (2)	C12—C13—C14—C9	1.1 (3)
C3—C2—C7—C8	−177.85 (16)	C14—C1—C2—C3	177.70 (17)
C3—C4—C5—C6	3.6 (3)	C14—C1—C2—C7	−2.4 (3)
C4—C5—C6—C7	−0.9 (3)	C14—C9—C10—C11	1.1 (3)
C5—C6—C7—C2	−3.5 (3)	C15—C8—C9—C10	0.7 (3)
C5—C6—C7—C8	179.56 (18)	C15—C8—C9—C14	−177.88 (16)
C6—C7—C8—C9	174.75 (17)	C15—C16—C17—O1	−173.18 (18)
C6—C7—C8—C15	−5.4 (3)	C15—C16—C17—O2	6.3 (3)
C7—C2—C3—C4	−2.6 (3)	C16—C17—O1—C18	179.04 (17)
C7—C8—C9—C10	−179.43 (17)	O2—C17—O1—C18	−0.5 (3)
C7—C8—C9—C14	2.0 (3)	Br1—C1—C2—C3	−3.1 (2)
C7—C8—C15—C16	−51.1 (3)	Br1—C1—C2—C7	176.78 (13)
C8—C9—C10—C11	−177.55 (18)	Br1—C1—C14—C9	−176.89 (13)
C8—C9—C14—C1	−2.0 (3)	Br1—C1—C14—C13	4.7 (2)
C8—C9—C14—C13	176.41 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···Cg1i	0.93	2.91 (2)	3.5055 (19)	123
C16—H16···O2ii	0.93	2.40	3.315 (3)	170
C5—H5···O2iii	0.93	2.53	3.372 (2)	150

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯Cg1i	0.93	2.91 (2)	3.5055 (19)	123
C16—H16⋯O2ii	0.93	2.40	3.315 (3)	170
C5—H5⋯O2iii	0.93	2.53	3.372 (2)	150

Symmetry codes: (i) ; (ii) ; (iii) .