Methyl 2-(7-benz-yloxy-1-naphth-yl)-2-oxoacetate.

In the crystal structure of the title compound, C(20)H(16)O(4), the naphthalene ring system makes dihedral angles of 43.79 (7) and 83.70 (9)°, respectively, with the mean planes of the phenyl ring and the acetate unit. C-H⋯π inter-actions involving all the aromatic six-membered rings are observed. The mol-ecules are stacked into columns along the a axis and adjacent columns are linked by weak C-H⋯O inter-actions.

Related literature

For related literature on hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For values of bond lengths, see: Allen et al. (1987 ▶). For related literature on bioactivities of compounds containing aromatic rings, see, for example: Hartwig (1998 ▶); Knepper et al. (2004 ▶); Kunz et al. (2003 ▶); Ley & Thomas (2003 ▶); Palucki et al. (1997 ▶).

Experimental

Crystal data

C20H16O4

M = 320.33

Orthorhombic,

a = 5.6145 (3) Å

b = 15.7422 (8) Å

c = 17.3843 (8) Å

V = 1536.50 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100.0 (1) K

0.58 × 0.32 × 0.10 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.946, T max = 0.991

17379 measured reflections

2575 independent reflections

2380 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.100

S = 1.08

2575 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); 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, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680801982X/is2310sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680801982X/is2310Isup2.hkl

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

C20H16O4	Dx = 1.385 Mg m−3
Mr = 320.33	Melting point: 358 K
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2575 reflections
a = 5.6145 (3) Å	θ = 1.8–30.0º
b = 15.7422 (8) Å	µ = 0.10 mm−1
c = 17.3843 (8) Å	T = 100.0 (1) K
V = 1536.50 (13) Å3	Plate, colourless
Z = 4	0.58 × 0.32 × 0.10 mm
F000 = 672

Bruker SMART APEXII CCD area-detector diffractometer	2575 independent reflections
Radiation source: fine-focus sealed tube	2380 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.039
Detector resolution: 8.33 pixels mm-1	θmax = 30.0º
T = 100.0(1) K	θmin = 1.8º
ω scans	h = −7→7
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −22→22
Tmin = 0.946, Tmax = 0.991	l = −22→24
17379 measured reflections

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)] = 0.034	H-atom parameters constrained
wR(F2) = 0.100	w = 1/[σ2(Fo2) + (0.0565P)2 + 0.2831P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.001
2575 reflections	Δρmax = 0.29 e Å−3
218 parameters	Δρmin = −0.17 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. The low-temparture data was collected with the Oxford Cryosystem Cobra low-temperature attachment.

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
O1	0.3014 (2)	0.54915 (8)	0.63643 (7)	0.0236 (3)
O2	0.8876 (3)	0.51454 (8)	0.43322 (7)	0.0253 (3)
O3	1.0904 (3)	0.35791 (8)	0.33767 (8)	0.0268 (3)
O4	1.3439 (2)	0.46196 (8)	0.37431 (7)	0.0222 (3)
C1	0.4708 (3)	0.48752 (10)	0.63241 (10)	0.0189 (3)
C2	0.4861 (4)	0.43676 (10)	0.69963 (10)	0.0223 (3)
H2A	0.3821	0.4459	0.7404	0.027*
C3	0.6541 (3)	0.37447 (10)	0.70417 (10)	0.0213 (3)
H3A	0.6623	0.3409	0.7481	0.026*
C4	0.8161 (3)	0.35991 (10)	0.64334 (9)	0.0187 (3)
C5	0.9937 (4)	0.29689 (10)	0.64975 (10)	0.0218 (3)
H5A	1.0026	0.2646	0.6944	0.026*
C6	1.1535 (3)	0.28219 (10)	0.59170 (10)	0.0226 (4)
H6A	1.2696	0.2405	0.5970	0.027*
C7	1.1400 (3)	0.33079 (10)	0.52406 (10)	0.0209 (3)
H7A	1.2462	0.3199	0.4842	0.025*
C8	0.9712 (3)	0.39479 (10)	0.51538 (9)	0.0182 (3)
C9	0.8007 (3)	0.41091 (10)	0.57529 (9)	0.0171 (3)
C10	0.6209 (3)	0.47439 (9)	0.57108 (9)	0.0177 (3)
H10A	0.6048	0.5070	0.5268	0.021*
C11	0.2839 (3)	0.60828 (10)	0.57358 (9)	0.0192 (3)
H11A	0.2236	0.5798	0.5281	0.023*
H11B	0.4396	0.6316	0.5618	0.023*
C12	0.1165 (3)	0.67811 (10)	0.59753 (9)	0.0183 (3)
C13	0.1697 (3)	0.76264 (10)	0.57956 (10)	0.0202 (3)
H13A	0.3105	0.7757	0.5540	0.024*
C14	0.0126 (3)	0.82699 (10)	0.59983 (10)	0.0212 (3)
H14A	0.0485	0.8830	0.5875	0.025*
C15	−0.1971 (3)	0.80841 (10)	0.63826 (10)	0.0219 (3)
H15A	−0.3026	0.8517	0.6510	0.026*
C16	−0.2495 (3)	0.72467 (11)	0.65769 (10)	0.0219 (3)
H16A	−0.3884	0.7120	0.6845	0.026*
C17	−0.0931 (3)	0.66001 (10)	0.63687 (10)	0.0198 (3)
H17A	−0.1293	0.6040	0.6494	0.024*
C18	0.9888 (3)	0.44716 (10)	0.44555 (10)	0.0187 (3)
C19	1.1476 (3)	0.41483 (10)	0.38003 (9)	0.0189 (3)
C20	1.4989 (4)	0.44233 (11)	0.30990 (10)	0.0232 (3)
H20A	1.6051	0.4891	0.3010	0.035*
H20B	1.4044	0.4326	0.2647	0.035*
H20C	1.5899	0.3923	0.3214	0.035*

	U11	U22	U33	U12	U13	U23
O1	0.0271 (7)	0.0212 (5)	0.0224 (6)	0.0087 (5)	0.0058 (5)	0.0049 (5)
O2	0.0272 (7)	0.0212 (5)	0.0274 (6)	0.0057 (5)	0.0047 (6)	0.0037 (5)
O3	0.0274 (7)	0.0242 (6)	0.0287 (6)	−0.0045 (6)	0.0028 (6)	−0.0071 (5)
O4	0.0216 (6)	0.0225 (5)	0.0224 (6)	−0.0041 (5)	0.0035 (5)	−0.0030 (5)
C1	0.0202 (8)	0.0157 (6)	0.0207 (7)	0.0022 (6)	0.0002 (7)	0.0000 (6)
C2	0.0264 (9)	0.0206 (7)	0.0198 (7)	0.0030 (7)	0.0034 (7)	0.0013 (6)
C3	0.0265 (9)	0.0190 (7)	0.0185 (7)	0.0011 (7)	−0.0011 (7)	0.0026 (6)
C4	0.0216 (8)	0.0146 (6)	0.0198 (7)	−0.0004 (6)	−0.0027 (7)	−0.0008 (6)
C5	0.0270 (9)	0.0175 (7)	0.0210 (8)	0.0019 (7)	−0.0059 (7)	0.0012 (6)
C6	0.0238 (9)	0.0171 (7)	0.0268 (8)	0.0036 (6)	−0.0041 (7)	−0.0003 (6)
C7	0.0201 (8)	0.0192 (7)	0.0233 (8)	0.0015 (7)	−0.0001 (7)	−0.0027 (6)
C8	0.0189 (8)	0.0159 (6)	0.0199 (7)	−0.0004 (6)	−0.0004 (6)	−0.0014 (6)
C9	0.0188 (7)	0.0142 (6)	0.0183 (7)	−0.0013 (6)	−0.0013 (6)	−0.0020 (5)
C10	0.0196 (8)	0.0158 (7)	0.0177 (7)	0.0006 (6)	−0.0014 (6)	0.0006 (6)
C11	0.0218 (8)	0.0184 (7)	0.0175 (7)	0.0026 (6)	0.0002 (6)	0.0015 (6)
C12	0.0189 (8)	0.0187 (7)	0.0174 (7)	0.0017 (6)	−0.0029 (6)	−0.0014 (6)
C13	0.0218 (8)	0.0197 (7)	0.0192 (7)	−0.0006 (6)	−0.0003 (7)	0.0018 (6)
C14	0.0268 (9)	0.0156 (7)	0.0210 (7)	−0.0003 (7)	−0.0033 (7)	−0.0001 (6)
C15	0.0244 (9)	0.0202 (7)	0.0211 (8)	0.0046 (7)	−0.0018 (7)	−0.0032 (6)
C16	0.0193 (8)	0.0248 (8)	0.0216 (8)	0.0010 (7)	−0.0004 (7)	−0.0011 (6)
C17	0.0194 (8)	0.0177 (6)	0.0224 (8)	−0.0003 (6)	−0.0020 (7)	0.0009 (6)
C18	0.0183 (7)	0.0177 (7)	0.0201 (7)	−0.0021 (6)	0.0007 (6)	−0.0021 (6)
C19	0.0185 (8)	0.0167 (6)	0.0214 (7)	0.0007 (6)	0.0000 (6)	0.0012 (6)
C20	0.0202 (8)	0.0262 (8)	0.0232 (8)	−0.0001 (7)	0.0046 (7)	0.0009 (6)

O1—C1	1.361 (2)	C8—C18	1.471 (2)
O1—C11	1.4387 (19)	C9—C10	1.422 (2)
O2—C18	1.222 (2)	C10—H10A	0.9300
O3—C19	1.204 (2)	C11—C12	1.505 (2)
O4—C19	1.332 (2)	C11—H11A	0.9700
O4—C20	1.452 (2)	C11—H11B	0.9700
C1—C10	1.375 (2)	C12—C17	1.391 (2)
C1—C2	1.418 (2)	C12—C13	1.399 (2)
C2—C3	1.363 (2)	C13—C14	1.389 (2)
C2—H2A	0.9300	C13—H13A	0.9300
C3—C4	1.414 (2)	C14—C15	1.385 (3)
C3—H3A	0.9300	C14—H14A	0.9300
C4—C5	1.411 (2)	C15—C16	1.392 (2)
C4—C9	1.432 (2)	C15—H15A	0.9300
C5—C6	1.370 (3)	C16—C17	1.392 (2)
C5—H5A	0.9300	C16—H16A	0.9300
C6—C7	1.405 (2)	C17—H17A	0.9300
C6—H6A	0.9300	C18—C19	1.534 (2)
C7—C8	1.391 (2)	C20—H20A	0.9600
C7—H7A	0.9300	C20—H20B	0.9600
C8—C9	1.437 (2)	C20—H20C	0.9600
C1—O1—C11	118.03 (13)	C12—C11—H11A	110.2
C19—O4—C20	115.80 (13)	O1—C11—H11B	110.2
O1—C1—C10	125.14 (14)	C12—C11—H11B	110.2
O1—C1—C2	113.69 (15)	H11A—C11—H11B	108.5
C10—C1—C2	121.15 (15)	C17—C12—C13	119.04 (16)
C3—C2—C1	119.68 (16)	C17—C12—C11	120.99 (15)
C3—C2—H2A	120.2	C13—C12—C11	119.97 (16)
C1—C2—H2A	120.2	C14—C13—C12	120.11 (17)
C2—C3—C4	121.24 (15)	C14—C13—H13A	119.9
C2—C3—H3A	119.4	C12—C13—H13A	119.9
C4—C3—H3A	119.4	C15—C14—C13	120.55 (15)
C5—C4—C3	120.65 (15)	C15—C14—H14A	119.7
C5—C4—C9	120.12 (16)	C13—C14—H14A	119.7
C3—C4—C9	119.22 (14)	C14—C15—C16	119.77 (16)
C6—C5—C4	121.56 (15)	C14—C15—H15A	120.1
C6—C5—H5A	119.2	C16—C15—H15A	120.1
C4—C5—H5A	119.2	C17—C16—C15	119.75 (17)
C5—C6—C7	119.30 (16)	C17—C16—H16A	120.1
C5—C6—H6A	120.4	C15—C16—H16A	120.1
C7—C6—H6A	120.4	C12—C17—C16	120.77 (15)
C8—C7—C6	121.45 (17)	C12—C17—H17A	119.6
C8—C7—H7A	119.3	C16—C17—H17A	119.6
C6—C7—H7A	119.3	O2—C18—C8	126.88 (16)
C7—C8—C9	120.19 (15)	O2—C18—C19	115.34 (15)
C7—C8—C18	116.73 (15)	C8—C18—C19	117.78 (14)
C9—C8—C18	122.94 (15)	O3—C19—O4	126.16 (16)
C10—C9—C4	118.63 (15)	O3—C19—C18	123.10 (16)
C10—C9—C8	124.02 (14)	O4—C19—C18	110.59 (14)
C4—C9—C8	117.35 (14)	O4—C20—H20A	109.5
C1—C10—C9	120.05 (14)	O4—C20—H20B	109.5
C1—C10—H10A	120.0	H20A—C20—H20B	109.5
C9—C10—H10A	120.0	O4—C20—H20C	109.5
O1—C11—C12	107.76 (13)	H20A—C20—H20C	109.5
O1—C11—H11A	110.2	H20B—C20—H20C	109.5
C11—O1—C1—C10	−3.3 (2)	C4—C9—C10—C1	1.9 (2)
C11—O1—C1—C2	175.28 (15)	C8—C9—C10—C1	−177.56 (15)
O1—C1—C2—C3	−177.83 (16)	C1—O1—C11—C12	−170.20 (14)
C10—C1—C2—C3	0.8 (3)	O1—C11—C12—C17	−42.1 (2)
C1—C2—C3—C4	0.7 (3)	O1—C11—C12—C13	138.51 (16)
C2—C3—C4—C5	178.08 (17)	C17—C12—C13—C14	−1.0 (3)
C2—C3—C4—C9	−0.9 (3)	C11—C12—C13—C14	178.34 (15)
C3—C4—C5—C6	−179.53 (16)	C12—C13—C14—C15	0.3 (3)
C9—C4—C5—C6	−0.6 (3)	C13—C14—C15—C16	0.9 (3)
C4—C5—C6—C7	−0.2 (3)	C14—C15—C16—C17	−1.4 (3)
C5—C6—C7—C8	1.4 (3)	C13—C12—C17—C16	0.5 (3)
C6—C7—C8—C9	−1.9 (3)	C11—C12—C17—C16	−178.85 (16)
C6—C7—C8—C18	174.04 (15)	C15—C16—C17—C12	0.7 (3)
C5—C4—C9—C10	−179.41 (15)	C7—C8—C18—O2	−166.30 (17)
C3—C4—C9—C10	−0.4 (2)	C9—C8—C18—O2	9.5 (3)
C5—C4—C9—C8	0.1 (2)	C7—C8—C18—C19	14.4 (2)
C3—C4—C9—C8	179.09 (15)	C9—C8—C18—C19	−169.81 (15)
C7—C8—C9—C10	−179.42 (15)	C20—O4—C19—O3	0.8 (2)
C18—C8—C9—C10	4.9 (3)	C20—O4—C19—C18	−174.75 (13)
C7—C8—C9—C4	1.1 (2)	O2—C18—C19—O3	−103.8 (2)
C18—C8—C9—C4	−174.57 (15)	C8—C18—C19—O3	75.6 (2)
O1—C1—C10—C9	176.33 (15)	O2—C18—C19—O4	71.91 (19)
C2—C1—C10—C9	−2.1 (3)	C8—C18—C19—O4	−108.69 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O2	0.93	2.28	2.896 (2)	124
C14—H14A···O2i	0.93	2.52	3.315 (2)	144
C20—H20B···O1ii	0.96	2.53	3.458 (2)	163
C7—H7A···Cg2iii	0.93	3.15	3.8529 (18)	134
C13—H13A···Cg3iv	0.93	3.13	3.8070 (19)	132
C17—H17A···Cg1v	0.93	3.12	4.0033 (17)	159

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C1–C4/C9–C10, C4–C9 and C12–C17 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯O2	0.93	2.28	2.896 (2)	124
C14—H14A⋯O2i	0.93	2.52	3.315 (2)	144
C20—H20B⋯O1ii	0.96	2.53	3.458 (2)	163
C7—H7A⋯Cg2iii	0.93	3.15	3.8529 (18)	134
C13—H13A⋯Cg3iv	0.93	3.13	3.8070 (19)	132
C17—H17A⋯Cg1v	0.93	3.12	4.0033 (17)	159

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