(2E)-Methyl 2-(7-benz-yloxy-1-naphth-yl)-3-meth-oxy-acrylate.

In the title compound, C(22)H(20)O(4), the dihedral angle between the phenyl and naphthalene ring systems is 86.10 (10)°. The methoxyacrylate group is disordered over two orientations in a 0.905 (3):0.095 (3) ratio.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For a related synthesis and crystal structure, see: Fun et al. (2008 ▶). For general background to and applications of compounds containing aromatic rings, see: Gunatilaka (2006 ▶); Kozikowski et al. (2000 ▶). Methyl­ene carbonyl compounds are often found in biologically active natural compounds, see: Gotthardt & Weisshuhn (1978 ▶); Shono et al. (1979 ▶).

Experimental

Crystal data

C22H20O4

M = 348.38

Monoclinic,

a = 10.996 (5) Å

b = 7.873 (5) Å

c = 21.417 (5) Å

β = 102.493 (5)°

V = 1810.2 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.4 × 0.4 × 0.3 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.826, T max = 0.973

21877 measured reflections

4203 independent reflections

3273 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.131

S = 1.04

4203 reflections

247 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 1999 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810020994/zq2038sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810020994/zq2038Isup2.hkl

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

C22H20O4	F(000) = 736
Mr = 348.38	Dx = 1.278 Mg m−3
Monoclinic, P21/n	Melting point = 398–399 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 10.996 (5) Å	Cell parameters from 7659 reflections
b = 7.873 (5) Å	θ = 2.3–27.6°
c = 21.417 (5) Å	µ = 0.09 mm−1
β = 102.493 (5)°	T = 293 K
V = 1810.2 (15) Å3	Block, colorless
Z = 4	0.4 × 0.4 × 0.3 mm

Bruker SMART CCD area-detector diffractometer	4203 independent reflections
Radiation source: fine-focus sealed tube	3273 reflections with I > 2σ(I)
graphite	Rint = 0.025
phi and ω scans	θmax = 27.6°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −14→14
Tmin = 0.826, Tmax = 0.973	k = −10→9
21877 measured reflections	l = −27→27

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0575P)2 + 0.3948P] where P = (Fo2 + 2Fc2)/3
4203 reflections	(Δ/σ)max = 0.020
247 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.17 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	Occ. (<1)
C1	0.89564 (15)	0.8419 (2)	0.43935 (8)	0.0617 (4)
H1	0.9075	0.9125	0.4750	0.074*
C2	0.9022 (2)	0.6687 (3)	0.44746 (13)	0.0899 (7)
H2	0.9175	0.6215	0.4882	0.108*
C3	0.8857 (2)	0.5660 (3)	0.39409 (18)	0.1101 (9)
H3	0.8900	0.4486	0.3991	0.132*
C4	0.8631 (2)	0.6339 (3)	0.33425 (16)	0.1042 (8)
H4	0.8528	0.5629	0.2988	0.125*
C5	0.85536 (18)	0.8070 (3)	0.32603 (10)	0.0768 (5)
H5	0.8392	0.8531	0.2851	0.092*
C6	0.87165 (13)	0.91229 (19)	0.37869 (7)	0.0515 (3)
C7	0.85480 (15)	1.1015 (2)	0.37234 (7)	0.0554 (4)
H7A	0.7704	1.1295	0.3755	0.067*
H7B	0.9111	1.1558	0.4079	0.067*
C8	0.99755 (14)	1.19352 (19)	0.30829 (6)	0.0497 (3)
C9	1.00816 (16)	1.2723 (2)	0.25038 (7)	0.0591 (4)
H9	0.9368	1.3001	0.2200	0.071*
C10	1.12174 (16)	1.3073 (2)	0.23908 (7)	0.0573 (4)
H10	1.1274	1.3592	0.2008	0.069*
C11	1.23257 (14)	1.26688 (17)	0.28418 (6)	0.0464 (3)
C12	1.22164 (13)	1.18630 (16)	0.34233 (6)	0.0411 (3)
C13	1.10149 (13)	1.15120 (17)	0.35316 (6)	0.0437 (3)
H13	1.0934	1.0991	0.3910	0.052*
C14	1.35110 (16)	1.3059 (2)	0.27324 (7)	0.0563 (4)
H14	1.3578	1.3577	0.2351	0.068*
C15	1.45600 (16)	1.2686 (2)	0.31784 (7)	0.0580 (4)
H15	1.5338	1.2961	0.3103	0.070*
C16	1.44661 (14)	1.18867 (19)	0.37519 (7)	0.0513 (3)
H16	1.5189	1.1635	0.4053	0.062*
C17	1.33331 (13)	1.14669 (16)	0.38795 (6)	0.0421 (3)
C18	1.32816 (12)	1.06687 (17)	0.45059 (6)	0.0431 (3)
C19	1.28723 (12)	0.89191 (18)	0.45565 (6)	0.0457 (3)
H19	1.2753	0.8435	0.4935	0.055*	0.095 (3)
O2A	1.26989 (13)	0.82617 (16)	0.50464 (5)	0.0647 (4)	0.905 (3)
C20	1.22339 (19)	0.6374 (2)	0.39907 (9)	0.0704 (5)
H20A	1.2762	0.5730	0.4323	0.106*
H20B	1.2236	0.5868	0.3583	0.106*
H20C	1.1400	0.6380	0.4060	0.106*
C21	1.36400 (13)	1.15235 (19)	0.50605 (6)	0.0495 (3)
H21	1.3621	1.0975	0.5443	0.059*	0.905 (3)
O2B	1.3729 (13)	1.076 (2)	0.5625 (5)	0.084 (5)	0.095 (3)
C22	1.43189 (19)	1.3923 (3)	0.56949 (8)	0.0780 (5)
H22A	1.3574	1.4053	0.5855	0.117*
H22B	1.4680	1.5019	0.5659	0.117*
H22C	1.4902	1.3228	0.5984	0.117*
O1	0.87669 (10)	1.16997 (16)	0.31413 (5)	0.0632 (3)
O3	1.26886 (10)	0.80927 (12)	0.39999 (5)	0.0546 (3)
O4	1.40199 (12)	1.31265 (15)	0.50759 (5)	0.0662 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0605 (9)	0.0539 (9)	0.0707 (10)	0.0037 (7)	0.0145 (8)	0.0037 (8)
C2	0.0809 (13)	0.0625 (12)	0.1244 (19)	0.0085 (10)	0.0181 (12)	0.0259 (12)
C3	0.0878 (16)	0.0439 (11)	0.194 (3)	0.0031 (10)	0.0207 (18)	−0.0089 (16)
C4	0.0886 (15)	0.0765 (15)	0.140 (2)	0.0046 (12)	0.0081 (15)	−0.0512 (16)
C5	0.0719 (11)	0.0777 (13)	0.0778 (12)	0.0062 (9)	0.0099 (9)	−0.0239 (10)
C6	0.0437 (7)	0.0521 (8)	0.0597 (8)	0.0019 (6)	0.0135 (6)	−0.0058 (7)
C7	0.0574 (8)	0.0559 (9)	0.0572 (8)	0.0078 (7)	0.0216 (7)	0.0049 (7)
C8	0.0570 (8)	0.0514 (8)	0.0415 (7)	0.0089 (6)	0.0122 (6)	0.0052 (6)
C9	0.0684 (10)	0.0673 (10)	0.0396 (7)	0.0144 (8)	0.0074 (7)	0.0125 (7)
C10	0.0792 (11)	0.0581 (9)	0.0362 (7)	0.0076 (8)	0.0160 (7)	0.0133 (6)
C11	0.0671 (9)	0.0404 (7)	0.0332 (6)	−0.0003 (6)	0.0144 (6)	0.0016 (5)
C12	0.0587 (8)	0.0342 (6)	0.0314 (6)	0.0007 (5)	0.0118 (5)	−0.0012 (5)
C13	0.0580 (8)	0.0413 (7)	0.0332 (6)	0.0042 (6)	0.0129 (5)	0.0055 (5)
C14	0.0783 (10)	0.0531 (9)	0.0423 (7)	−0.0088 (7)	0.0238 (7)	0.0048 (6)
C15	0.0643 (9)	0.0628 (10)	0.0515 (8)	−0.0155 (8)	0.0223 (7)	−0.0018 (7)
C16	0.0568 (8)	0.0534 (8)	0.0438 (7)	−0.0064 (7)	0.0111 (6)	−0.0024 (6)
C17	0.0571 (8)	0.0377 (6)	0.0326 (6)	−0.0025 (6)	0.0119 (5)	−0.0024 (5)
C18	0.0478 (7)	0.0468 (7)	0.0341 (6)	0.0029 (6)	0.0079 (5)	0.0027 (5)
C19	0.0497 (7)	0.0477 (8)	0.0396 (6)	0.0056 (6)	0.0092 (5)	0.0053 (6)
O2A	0.0923 (10)	0.0599 (8)	0.0444 (7)	−0.0086 (6)	0.0204 (6)	0.0093 (5)
C20	0.0862 (12)	0.0485 (9)	0.0765 (11)	−0.0104 (8)	0.0171 (9)	−0.0040 (8)
C21	0.0541 (8)	0.0563 (9)	0.0373 (6)	0.0015 (7)	0.0080 (6)	0.0019 (6)
O2B	0.084 (9)	0.134 (14)	0.030 (6)	0.019 (9)	0.008 (5)	0.004 (7)
C22	0.0847 (12)	0.0914 (14)	0.0562 (10)	−0.0192 (10)	0.0114 (8)	−0.0297 (9)
O1	0.0549 (6)	0.0787 (8)	0.0559 (6)	0.0109 (5)	0.0117 (5)	0.0176 (5)
O3	0.0762 (7)	0.0432 (5)	0.0462 (5)	−0.0023 (5)	0.0168 (5)	−0.0016 (4)
O4	0.0954 (9)	0.0593 (7)	0.0424 (6)	−0.0142 (6)	0.0114 (5)	−0.0093 (5)

C1—C2	1.375 (3)	C12—C13	1.417 (2)
C1—C6	1.384 (2)	C12—C17	1.4285 (19)
C1—H1	0.9300	C13—H13	0.9300
C2—C3	1.380 (4)	C14—C15	1.361 (2)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.361 (4)	C15—C16	1.404 (2)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.375 (3)	C16—C17	1.372 (2)
C4—H4	0.9300	C16—H16	0.9300
C5—C6	1.380 (2)	C17—C18	1.4936 (17)
C5—H5	0.9300	C18—C21	1.3477 (19)
C6—C7	1.504 (2)	C18—C19	1.460 (2)
C7—O1	1.4255 (17)	C19—O3	1.3345 (16)
C7—H7A	0.9700	C19—H19	0.9300
C7—H7B	0.9700	C20—O3	1.441 (2)
C8—C13	1.366 (2)	C20—H20A	0.9600
C8—O1	1.3741 (19)	C20—H20B	0.9600
C8—C9	1.414 (2)	C20—H20C	0.9600
C9—C10	1.351 (2)	C21—O4	1.328 (2)
C9—H9	0.9300	C21—H21	0.9300
C10—C11	1.418 (2)	C22—O4	1.4388 (18)
C10—H10	0.9300	C22—H22A	0.9600
C11—C14	1.407 (2)	C22—H22B	0.9600
C11—C12	1.4258 (17)	C22—H22C	0.9600
C2—C1—C6	120.64 (19)	C8—C13—C12	120.35 (12)
C2—C1—H1	119.7	C8—C13—H13	119.8
C6—C1—H1	119.7	C12—C13—H13	119.8
C1—C2—C3	118.9 (2)	C15—C14—C11	120.73 (13)
C1—C2—H2	120.6	C15—C14—H14	119.6
C3—C2—H2	120.6	C11—C14—H14	119.6
C4—C3—C2	121.0 (2)	C14—C15—C16	119.95 (14)
C4—C3—H3	119.5	C14—C15—H15	120.0
C2—C3—H3	119.5	C16—C15—H15	120.0
C3—C4—C5	120.2 (2)	C17—C16—C15	121.60 (14)
C3—C4—H4	119.9	C17—C16—H16	119.2
C5—C4—H4	119.9	C15—C16—H16	119.2
C4—C5—C6	119.8 (2)	C16—C17—C12	119.62 (12)
C4—C5—H5	120.1	C16—C17—C18	119.51 (12)
C6—C5—H5	120.1	C12—C17—C18	120.81 (11)
C5—C6—C1	119.45 (17)	C21—C18—C19	116.21 (12)
C5—C6—C7	121.96 (16)	C21—C18—C17	121.38 (13)
C1—C6—C7	118.43 (14)	C19—C18—C17	122.39 (11)
O1—C7—C6	114.39 (13)	O3—C19—C18	112.53 (11)
O1—C7—H7A	108.7	O3—C19—H19	123.7
C6—C7—H7A	108.7	C18—C19—H19	123.7
O1—C7—H7B	108.7	O3—C20—H20A	109.5
C6—C7—H7B	108.7	O3—C20—H20B	109.5
H7A—C7—H7B	107.6	H20A—C20—H20B	109.5
C13—C8—O1	125.56 (12)	O3—C20—H20C	109.5
C13—C8—C9	120.59 (14)	H20A—C20—H20C	109.5
O1—C8—C9	113.83 (13)	H20B—C20—H20C	109.5
C10—C9—C8	120.10 (14)	O4—C21—C18	121.81 (13)
C10—C9—H9	120.0	O4—C21—H21	119.1
C8—C9—H9	120.0	C18—C21—H21	119.1
C9—C10—C11	121.59 (13)	O4—C22—H22A	109.5
C9—C10—H10	119.2	O4—C22—H22B	109.5
C11—C10—H10	119.2	H22A—C22—H22B	109.5
C14—C11—C10	121.88 (13)	O4—C22—H22C	109.5
C14—C11—C12	119.91 (13)	H22A—C22—H22C	109.5
C10—C11—C12	118.20 (13)	H22B—C22—H22C	109.5
C13—C12—C11	119.17 (12)	C8—O1—C7	118.70 (11)
C13—C12—C17	122.65 (11)	C19—O3—C20	117.07 (12)
C11—C12—C17	118.17 (12)	C21—O4—C22	116.43 (13)