Methyl 2-(5-bromo-2-methyl-naphtho[2,1-b]furan-1-yl)acetate.

The three fused six-, six- and five-membered rings in the title compound, C(16)H(13)BrO(3), are coplanar, the CH(2)C(=O)OCH(3) residue being twisted out of this plane [dihedral angle = -26.9 (4)°]. Centrosymmetric dimers are found in the crystal structure stabilized by C-H⋯O inter-actions involving the furan O atom.

Related literature

For related literature, see: Chatterjea et al. (1979 ▶); Einhorn et al. (1983 ▶); Monte et al. (1996 ▶); Jevric et al. (2008 ▶).

Experimental

Crystal data

C16H13BrO3

M = 333.17

Monoclinic,

a = 17.050 (2) Å

b = 14.5064 (17) Å

c = 5.3660 (7) Å

β = 96.443 (3)°

V = 1318.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 3.12 mm−1

T = 223 (2) K

0.68 × 0.18 × 0.16 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.492, T max = 1.000 (expected range = 0.299–0.607)

10676 measured reflections

3817 independent reflections

2967 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.136

S = 1.13

3817 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.77 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808015511/su2059sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808015511/su2059Isup2.hkl

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

C16H13BrO3	F000 = 672
Mr = 333.17	Dx = 1.678 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 2984 reflections
a = 17.050 (2) Å	θ = 2.4–29.7º
b = 14.5064 (17) Å	µ = 3.12 mm−1
c = 5.3660 (7) Å	T = 223 (2) K
β = 96.443 (3)º	Plate, pale-yellow
V = 1318.8 (3) Å3	0.68 × 0.18 × 0.16 mm
Z = 4

Bruker SMART CCD diffractometer	3817 independent reflections
Radiation source: fine-focus sealed tube	2967 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.035
T = 223(2) K	θmax = 30.1º
ω scans	θmin = 1.2º
Absorption correction: multi-scan(SADABS; Bruker, 2000)	h = −23→23
Tmin = 0.492, Tmax = 1.0	k = −14→20
10676 measured reflections	l = −7→7

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)] = 0.044	H-atom parameters constrained
wR(F2) = 0.136	w = 1/[σ2(Fo2) + (0.0586P)2 + 0.71P] where P = (Fo2 + 2Fc2)/3
S = 1.13	(Δ/σ)max < 0.001
3817 reflections	Δρmax = 0.47 e Å−3
183 parameters	Δρmin = −0.77 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
Br5	0.04963 (2)	0.33514 (2)	−0.16830 (6)	0.04284 (14)
O3	0.10671 (11)	0.56263 (13)	0.5779 (4)	0.0285 (4)
O12	0.33445 (13)	0.68019 (14)	0.3251 (4)	0.0321 (4)
O13	0.44151 (12)	0.62588 (17)	0.5516 (4)	0.0379 (5)
C1	0.23909 (16)	0.56919 (18)	0.6116 (5)	0.0242 (5)
C2	0.17380 (16)	0.60179 (18)	0.7005 (5)	0.0258 (5)
C3A	0.13162 (16)	0.50429 (18)	0.4058 (5)	0.0262 (5)
C4	0.08136 (18)	0.45375 (19)	0.2380 (5)	0.0308 (6)
H4	0.0263	0.4554	0.2388	0.037*
C5	0.11641 (18)	0.40163 (19)	0.0720 (5)	0.0307 (6)
C5A	0.19934 (18)	0.39606 (18)	0.0699 (5)	0.0293 (6)
C6	0.2347 (2)	0.34180 (19)	−0.1028 (6)	0.0384 (7)
H6	0.2027	0.3084	−0.2251	0.046*
C7	0.3142 (2)	0.3368 (2)	−0.0963 (6)	0.0422 (8)
H7	0.3368	0.3005	−0.2146	0.051*
C8	0.3627 (2)	0.3850 (2)	0.0844 (6)	0.0371 (7)
H8	0.4178	0.3802	0.0899	0.044*
C9	0.33055 (18)	0.43933 (19)	0.2536 (5)	0.0306 (6)
H9	0.3639	0.4719	0.3744	0.037*
C9A	0.24847 (17)	0.44736 (18)	0.2501 (5)	0.0268 (5)
C9B	0.21225 (16)	0.50423 (17)	0.4179 (5)	0.0242 (5)
C11	0.32098 (16)	0.59630 (19)	0.7023 (5)	0.0259 (5)
H11A	0.3502	0.5416	0.7670	0.031*
H11B	0.3199	0.6399	0.8413	0.031*
C12	0.36339 (16)	0.63946 (18)	0.5035 (5)	0.0258 (5)
C13	0.4870 (2)	0.6604 (3)	0.3638 (8)	0.0546 (10)
H13A	0.4710	0.6295	0.2058	0.082*
H13B	0.5425	0.6489	0.4141	0.082*
H13C	0.4782	0.7262	0.3438	0.082*
C21	0.16031 (19)	0.66841 (19)	0.8973 (6)	0.0315 (6)
H21A	0.1419	0.6362	1.0380	0.047*
H21B	0.1209	0.7129	0.8313	0.047*
H21C	0.2093	0.7001	0.9526	0.047*

	U11	U22	U33	U12	U13	U23
Br5	0.0624 (3)	0.0341 (2)	0.02918 (18)	−0.01456 (14)	−0.00759 (14)	−0.00306 (11)
O3	0.0299 (10)	0.0309 (10)	0.0251 (9)	−0.0050 (8)	0.0054 (7)	−0.0038 (8)
O12	0.0351 (11)	0.0337 (11)	0.0268 (10)	0.0006 (8)	0.0003 (8)	0.0070 (8)
O13	0.0265 (10)	0.0498 (13)	0.0375 (12)	0.0037 (9)	0.0032 (9)	0.0119 (10)
C1	0.0328 (14)	0.0211 (11)	0.0183 (11)	−0.0022 (10)	0.0018 (9)	0.0015 (9)
C2	0.0310 (13)	0.0232 (12)	0.0231 (12)	−0.0028 (10)	0.0025 (10)	0.0012 (9)
C3A	0.0322 (14)	0.0246 (12)	0.0221 (11)	−0.0042 (10)	0.0047 (10)	0.0012 (10)
C4	0.0345 (15)	0.0304 (14)	0.0267 (13)	−0.0095 (11)	0.0005 (11)	0.0013 (11)
C5	0.0427 (16)	0.0240 (12)	0.0238 (12)	−0.0093 (11)	−0.0036 (11)	0.0019 (10)
C5A	0.0463 (16)	0.0208 (12)	0.0206 (12)	−0.0010 (11)	0.0035 (11)	0.0027 (9)
C6	0.064 (2)	0.0249 (14)	0.0262 (14)	0.0001 (13)	0.0036 (13)	−0.0017 (11)
C7	0.069 (2)	0.0293 (15)	0.0304 (15)	0.0110 (15)	0.0131 (15)	−0.0013 (12)
C8	0.0463 (17)	0.0279 (14)	0.0382 (16)	0.0105 (13)	0.0101 (13)	0.0048 (12)
C9	0.0400 (15)	0.0239 (13)	0.0283 (13)	0.0031 (11)	0.0058 (11)	0.0036 (10)
C9A	0.0383 (15)	0.0198 (12)	0.0227 (12)	0.0002 (10)	0.0052 (10)	0.0030 (9)
C9B	0.0333 (14)	0.0191 (11)	0.0198 (11)	−0.0032 (10)	0.0010 (10)	0.0022 (9)
C11	0.0298 (13)	0.0262 (13)	0.0207 (11)	−0.0016 (10)	−0.0020 (10)	0.0021 (9)
C12	0.0294 (13)	0.0232 (12)	0.0239 (12)	0.0003 (10)	−0.0009 (10)	−0.0032 (9)
C13	0.0363 (18)	0.079 (3)	0.051 (2)	−0.0019 (17)	0.0130 (16)	0.0162 (19)
C21	0.0381 (15)	0.0305 (14)	0.0265 (13)	−0.0039 (12)	0.0068 (11)	−0.0034 (11)

Br5—C5	1.887 (3)	C6—H6	0.9400
O3—C3A	1.355 (3)	C7—C8	1.390 (5)
O3—C2	1.377 (3)	C7—H7	0.9400
O12—C12	1.184 (3)	C8—C9	1.362 (4)
O13—C12	1.343 (3)	C8—H8	0.9400
O13—C13	1.429 (4)	C9—C9A	1.402 (4)
C1—C2	1.345 (4)	C9—H9	0.9400
C1—C9B	1.439 (3)	C9A—C9B	1.413 (4)
C1—C11	1.479 (4)	C11—C12	1.492 (4)
C2—C21	1.468 (4)	C11—H11A	0.9800
C3A—C9B	1.369 (4)	C11—H11B	0.9800
C3A—C4	1.382 (4)	C13—H13A	0.9700
C4—C5	1.357 (4)	C13—H13B	0.9700
C4—H4	0.9400	C13—H13C	0.9700
C5—C5A	1.417 (4)	C21—H21A	0.9700
C5A—C6	1.403 (4)	C21—H21B	0.9700
C5A—C9A	1.417 (4)	C21—H21C	0.9700
C6—C7	1.354 (6)
C3A—O3—C2	106.0 (2)	C8—C9—H9	119.5
C12—O13—C13	114.7 (2)	C9A—C9—H9	119.5
C2—C1—C9B	106.1 (2)	C9—C9A—C9B	123.1 (3)
C2—C1—C11	125.3 (2)	C9—C9A—C5A	118.6 (3)
C9B—C1—C11	128.6 (2)	C9B—C9A—C5A	118.3 (3)
C1—C2—O3	111.2 (2)	C3A—C9B—C9A	118.6 (2)
C1—C2—C21	133.6 (3)	C3A—C9B—C1	105.7 (2)
O3—C2—C21	115.2 (2)	C9A—C9B—C1	135.7 (3)
O3—C3A—C9B	111.0 (2)	C1—C11—C12	113.1 (2)
O3—C3A—C4	123.8 (3)	C1—C11—H11A	109.0
C9B—C3A—C4	125.2 (3)	C12—C11—H11A	109.0
C5—C4—C3A	115.9 (3)	C1—C11—H11B	109.0
C5—C4—H4	122.1	C12—C11—H11B	109.0
C3A—C4—H4	122.1	H11A—C11—H11B	107.8
C4—C5—C5A	123.4 (3)	O12—C12—O13	122.9 (3)
C4—C5—Br5	117.2 (2)	O12—C12—C11	126.6 (3)
C5A—C5—Br5	119.4 (2)	O13—C12—C11	110.6 (2)
C6—C5A—C9A	118.7 (3)	O13—C13—H13A	109.5
C6—C5A—C5	122.7 (3)	O13—C13—H13B	109.5
C9A—C5A—C5	118.6 (3)	H13A—C13—H13B	109.5
C7—C6—C5A	121.1 (3)	O13—C13—H13C	109.5
C7—C6—H6	119.5	H13A—C13—H13C	109.5
C5A—C6—H6	119.5	H13B—C13—H13C	109.5
C6—C7—C8	120.4 (3)	C2—C21—H21A	109.5
C6—C7—H7	119.8	C2—C21—H21B	109.5
C8—C7—H7	119.8	H21A—C21—H21B	109.5
C9—C8—C7	120.2 (3)	C2—C21—H21C	109.5
C9—C8—H8	119.9	H21A—C21—H21C	109.5
C7—C8—H8	119.9	H21B—C21—H21C	109.5
C8—C9—C9A	121.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O3i	0.94	2.58	3.468 (4)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O3i	0.94	2.58	3.468 (4)	157

Symmetry code: (i) .