Methyl 4-(2,7-dimeth-oxy-1-naphtho-yl)benzoate.

In the title compound, C(21)H(18)O(5), the dihedral angle between the naphthalene ring system and the benzene ring is 86.65 (6)°. The bridging carbonyl C-C(=O)-C plane makes dihedral angles of 83.57 (7) and 20.21 (8)°, respectively, with the naphthalene ring system and the benzene ring. The ester O-C=O plane and the benzene ring are almost coplanar, making a dihedral angle of 3.81 (18)°. The two meth-oxy groups lie essentially in the naphthalene ring plane [C-O-C-C torsion angles = 2.1 (2) and -1.44 (19)°]. In the crystal structure, a centrosymmetric dimer is formed through C-H⋯O bonds connecting the 7-meth-oxy group and the carbonyl O atom of the ester group. The dimers are further linked by C-H⋯O hydrogen bonds between the methoxy-carbonyl group and the bridging carbonyl O atom.

Related literature

For electrophilic aromatic substitution of naphthalene derivatives, see: Okamoto & Yonezawa (2009 ▶). For the structures of closely related compounds, see: Mitsui, Nakaema, Noguchi et al. (2008 ▶); Mitsui, Nakaema, Noguchi & Yonezawa (2008 ▶); Mitsui et al. (2009 ▶); Watanabe et al. (2010 ▶).

Experimental

Crystal data

C21H18O5

M = 350.35

Triclinic,

a = 7.7714 (2) Å

b = 9.5195 (3) Å

c = 12.2737 (4) Å

α = 97.525 (2)°

β = 97.919 (2)°

γ = 106.630 (2)°

V = 847.73 (5) Å3

Z = 2

Cu Kα radiation

μ = 0.81 mm−1

T = 193 K

0.40 × 0.20 × 0.05 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.816, T max = 0.960

15482 measured reflections

3066 independent reflections

2571 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.117

S = 1.08

3066 reflections

239 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.20 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681000382X/is2518sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681000382X/is2518Isup2.hkl

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

C21H18O5	Z = 2
Mr = 350.35	F(000) = 368
Triclinic, P1	Dx = 1.373 Mg m−3
Hall symbol: -P 1	Melting point = 427.6–430.1 K
a = 7.7714 (2) Å	Cu Kα radiation, λ = 1.54187 Å
b = 9.5195 (3) Å	Cell parameters from 10631 reflections
c = 12.2737 (4) Å	θ = 3.7–68.2°
α = 97.525 (2)°	µ = 0.81 mm−1
β = 97.919 (2)°	T = 193 K
γ = 106.630 (2)°	Block, yellow
V = 847.73 (5) Å3	0.40 × 0.20 × 0.05 mm

Rigaku R-AXIS RAPID diffractometer	3066 independent reflections
Radiation source: rotating anode	2571 reflections with I > 2σ(I)
graphite	Rint = 0.029
Detector resolution: 10.00 pixels mm-1	θmax = 68.2°, θmin = 3.7°
ω scans	h = −9→9
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −11→11
Tmin = 0.816, Tmax = 0.960	l = −14→14
15482 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037	H-atom parameters constrained
wR(F2) = 0.117	w = 1/[σ2(Fo2) + (0.0674P)2 + 0.1365P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
3066 reflections	Δρmax = 0.24 e Å−3
239 parameters	Δρmin = −0.20 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0056 (9)

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	1.18952 (13)	0.98013 (12)	0.33288 (8)	0.0454 (3)
O2	0.76893 (17)	0.46407 (13)	0.65183 (9)	0.0570 (3)
O3	0.59054 (13)	0.32936 (11)	0.49174 (8)	0.0423 (3)
O4	0.76938 (14)	1.00486 (13)	0.26247 (8)	0.0470 (3)
O5	1.29922 (14)	0.59184 (12)	0.00036 (9)	0.0479 (3)
C1	0.94439 (17)	0.87694 (14)	0.17801 (11)	0.0320 (3)
C2	0.80587 (18)	0.93926 (15)	0.16515 (12)	0.0363 (3)
C3	0.7095 (2)	0.93512 (17)	0.05840 (12)	0.0420 (4)
H3	0.6144	0.9794	0.0502	0.050*
C4	0.7548 (2)	0.86624 (17)	−0.03362 (12)	0.0431 (4)
H4	0.6898	0.8635	−0.1058	0.052*
C5	0.89479 (18)	0.79937 (15)	−0.02438 (11)	0.0351 (3)
C6	0.9413 (2)	0.72579 (16)	−0.11830 (12)	0.0426 (4)
H6	0.8780	0.7228	−0.1910	0.051*
C7	1.0735 (2)	0.65969 (16)	−0.10717 (12)	0.0439 (4)
H7	1.1012	0.6098	−0.1715	0.053*
C8	1.17077 (19)	0.66469 (15)	0.00021 (12)	0.0375 (3)
C9	1.13305 (18)	0.73542 (15)	0.09430 (11)	0.0342 (3)
H9	1.1997	0.7383	0.1659	0.041*
C10	0.99256 (17)	0.80497 (14)	0.08386 (11)	0.0326 (3)
C11	1.04313 (18)	0.88600 (15)	0.29455 (11)	0.0334 (3)
C12	0.95508 (17)	0.77299 (15)	0.36010 (11)	0.0328 (3)
C13	1.00721 (19)	0.79937 (16)	0.47627 (11)	0.0370 (3)
H13	1.0970	0.8899	0.5134	0.044*
C14	0.92869 (19)	0.69435 (16)	0.53730 (11)	0.0391 (3)
H14	0.9634	0.7133	0.6164	0.047*
C15	0.79879 (18)	0.56076 (16)	0.48323 (11)	0.0352 (3)
C16	0.74621 (19)	0.53386 (16)	0.36727 (11)	0.0370 (3)
H16	0.6573	0.4429	0.3301	0.044*
C17	0.82356 (18)	0.63965 (15)	0.30640 (11)	0.0358 (3)
H17	0.7869	0.6214	0.2274	0.043*
C18	0.6225 (2)	1.0673 (2)	0.25460 (15)	0.0519 (4)
H18A	0.6111	1.1086	0.3297	0.062*
H18B	0.5085	0.9895	0.2185	0.062*
H18C	0.6472	1.1467	0.2101	0.062*
C19	1.4033 (2)	0.59325 (18)	0.10659 (13)	0.0460 (4)
H19A	1.4865	0.5344	0.0961	0.055*
H19B	1.3203	0.5502	0.1553	0.055*
H19C	1.4742	0.6961	0.1411	0.055*
C20	0.72025 (19)	0.44915 (16)	0.55271 (11)	0.0381 (3)
C21	0.5110 (2)	0.21403 (17)	0.55273 (13)	0.0466 (4)
H21A	0.4122	0.1347	0.5020	0.056*
H21B	0.4621	0.2568	0.6138	0.056*
H21C	0.6051	0.1726	0.5835	0.056*

	U11	U22	U33	U12	U13	U23
O1	0.0398 (6)	0.0492 (6)	0.0360 (5)	0.0012 (5)	0.0004 (4)	0.0041 (5)
O2	0.0752 (8)	0.0539 (7)	0.0302 (6)	0.0028 (6)	0.0075 (5)	0.0079 (5)
O3	0.0465 (6)	0.0410 (6)	0.0352 (5)	0.0071 (4)	0.0065 (4)	0.0075 (4)
O4	0.0489 (6)	0.0594 (7)	0.0394 (6)	0.0285 (5)	0.0095 (5)	0.0043 (5)
O5	0.0547 (6)	0.0520 (6)	0.0406 (6)	0.0230 (5)	0.0140 (5)	0.0008 (5)
C1	0.0331 (7)	0.0312 (7)	0.0297 (7)	0.0068 (5)	0.0052 (5)	0.0061 (5)
C2	0.0357 (7)	0.0351 (7)	0.0363 (7)	0.0084 (6)	0.0066 (6)	0.0063 (6)
C3	0.0391 (8)	0.0460 (8)	0.0414 (8)	0.0157 (6)	0.0006 (6)	0.0116 (7)
C4	0.0450 (8)	0.0437 (8)	0.0349 (7)	0.0074 (6)	−0.0021 (6)	0.0113 (6)
C5	0.0393 (7)	0.0317 (7)	0.0285 (7)	0.0033 (6)	0.0031 (5)	0.0059 (5)
C6	0.0530 (9)	0.0391 (8)	0.0283 (7)	0.0047 (7)	0.0041 (6)	0.0054 (6)
C7	0.0572 (9)	0.0394 (8)	0.0313 (7)	0.0098 (7)	0.0117 (6)	0.0017 (6)
C8	0.0407 (7)	0.0325 (7)	0.0374 (7)	0.0077 (6)	0.0112 (6)	0.0035 (6)
C9	0.0383 (7)	0.0328 (7)	0.0292 (7)	0.0077 (6)	0.0065 (5)	0.0048 (5)
C10	0.0355 (7)	0.0289 (7)	0.0290 (7)	0.0030 (5)	0.0055 (5)	0.0058 (5)
C11	0.0361 (7)	0.0349 (7)	0.0290 (7)	0.0130 (6)	0.0059 (5)	0.0006 (5)
C12	0.0338 (7)	0.0366 (7)	0.0287 (7)	0.0139 (6)	0.0047 (5)	0.0028 (5)
C13	0.0401 (7)	0.0375 (7)	0.0290 (7)	0.0096 (6)	0.0020 (5)	0.0005 (6)
C14	0.0452 (8)	0.0445 (8)	0.0251 (6)	0.0127 (6)	0.0039 (5)	0.0027 (6)
C15	0.0388 (7)	0.0392 (8)	0.0304 (7)	0.0164 (6)	0.0073 (5)	0.0057 (6)
C16	0.0414 (7)	0.0345 (7)	0.0317 (7)	0.0099 (6)	0.0024 (6)	0.0023 (6)
C17	0.0414 (7)	0.0387 (8)	0.0254 (6)	0.0129 (6)	0.0020 (5)	0.0027 (6)
C18	0.0459 (9)	0.0587 (10)	0.0587 (10)	0.0274 (8)	0.0132 (7)	0.0078 (8)
C19	0.0449 (8)	0.0487 (9)	0.0463 (9)	0.0180 (7)	0.0103 (6)	0.0051 (7)
C20	0.0428 (8)	0.0407 (8)	0.0310 (7)	0.0140 (6)	0.0078 (6)	0.0041 (6)
C21	0.0498 (9)	0.0439 (9)	0.0462 (9)	0.0121 (7)	0.0118 (7)	0.0109 (7)

O1—C11	1.2154 (16)	C9—C10	1.4298 (19)
O2—C20	1.2002 (17)	C9—H9	0.9500
O3—C20	1.3368 (17)	C11—C12	1.4933 (18)
O3—C21	1.4499 (17)	C12—C17	1.3939 (19)
O4—C2	1.3772 (17)	C12—C13	1.3960 (18)
O4—C18	1.4277 (18)	C13—C14	1.381 (2)
O5—C8	1.3687 (17)	C13—H13	0.9500
O5—C19	1.4327 (18)	C14—C15	1.391 (2)
C1—C2	1.3708 (19)	C14—H14	0.9500
C1—C10	1.4154 (19)	C15—C16	1.3937 (19)
C1—C11	1.5065 (18)	C15—C20	1.496 (2)
C2—C3	1.407 (2)	C16—C17	1.3813 (19)
C3—C4	1.370 (2)	C16—H16	0.9500
C3—H3	0.9500	C17—H17	0.9500
C4—C5	1.408 (2)	C18—H18A	0.9800
C4—H4	0.9500	C18—H18B	0.9800
C5—C6	1.413 (2)	C18—H18C	0.9800
C5—C10	1.4231 (18)	C19—H19A	0.9800
C6—C7	1.351 (2)	C19—H19B	0.9800
C6—H6	0.9500	C19—H19C	0.9800
C7—C8	1.414 (2)	C21—H21A	0.9800
C7—H7	0.9500	C21—H21B	0.9800
C8—C9	1.3695 (19)	C21—H21C	0.9800
C20—O3—C21	115.70 (11)	C13—C12—C11	119.85 (12)
C2—O4—C18	118.25 (12)	C14—C13—C12	120.21 (13)
C8—O5—C19	117.18 (11)	C14—C13—H13	119.9
C2—C1—C10	120.65 (12)	C12—C13—H13	119.9
C2—C1—C11	118.48 (12)	C13—C14—C15	120.17 (12)
C10—C1—C11	120.86 (12)	C13—C14—H14	119.9
C1—C2—O4	115.70 (12)	C15—C14—H14	119.9
C1—C2—C3	121.08 (14)	C14—C15—C16	119.85 (13)
O4—C2—C3	123.22 (13)	C14—C15—C20	118.23 (12)
C4—C3—C2	118.99 (14)	C16—C15—C20	121.91 (12)
C4—C3—H3	120.5	C17—C16—C15	119.91 (13)
C2—C3—H3	120.5	C17—C16—H16	120.0
C3—C4—C5	121.91 (13)	C15—C16—H16	120.0
C3—C4—H4	119.0	C16—C17—C12	120.43 (12)
C5—C4—H4	119.0	C16—C17—H17	119.8
C4—C5—C6	122.64 (13)	C12—C17—H17	119.8
C4—C5—C10	118.76 (13)	O4—C18—H18A	109.5
C6—C5—C10	118.61 (13)	O4—C18—H18B	109.5
C7—C6—C5	121.56 (13)	H18A—C18—H18B	109.5
C7—C6—H6	119.2	O4—C18—H18C	109.5
C5—C6—H6	119.2	H18A—C18—H18C	109.5
C6—C7—C8	120.04 (14)	H18B—C18—H18C	109.5
C6—C7—H7	120.0	O5—C19—H19A	109.5
C8—C7—H7	120.0	O5—C19—H19B	109.5
O5—C8—C9	124.51 (13)	H19A—C19—H19B	109.5
O5—C8—C7	114.37 (12)	O5—C19—H19C	109.5
C9—C8—C7	121.10 (14)	H19A—C19—H19C	109.5
C8—C9—C10	119.48 (13)	H19B—C19—H19C	109.5
C8—C9—H9	120.3	O2—C20—O3	123.51 (13)
C10—C9—H9	120.3	O2—C20—C15	124.10 (13)
C1—C10—C5	118.60 (13)	O3—C20—C15	112.39 (11)
C1—C10—C9	122.18 (12)	O3—C21—H21A	109.5
C5—C10—C9	119.20 (12)	O3—C21—H21B	109.5
O1—C11—C12	121.49 (12)	H21A—C21—H21B	109.5
O1—C11—C1	121.30 (12)	O3—C21—H21C	109.5
C12—C11—C1	117.20 (11)	H21A—C21—H21C	109.5
C17—C12—C13	119.41 (12)	H21B—C21—H21C	109.5
C17—C12—C11	120.72 (11)
C10—C1—C2—O4	179.30 (11)	C6—C5—C10—C9	−0.47 (18)
C11—C1—C2—O4	−0.32 (18)	C8—C9—C10—C1	178.58 (11)
C10—C1—C2—C3	−0.8 (2)	C8—C9—C10—C5	−0.08 (18)
C11—C1—C2—C3	179.60 (12)	C2—C1—C11—O1	−98.98 (16)
C18—O4—C2—C1	−177.96 (12)	C10—C1—C11—O1	81.40 (17)
C18—O4—C2—C3	2.1 (2)	C2—C1—C11—C12	82.03 (15)
C1—C2—C3—C4	0.6 (2)	C10—C1—C11—C12	−97.59 (14)
O4—C2—C3—C4	−179.50 (13)	O1—C11—C12—C17	−158.78 (14)
C2—C3—C4—C5	0.1 (2)	C1—C11—C12—C17	20.22 (18)
C3—C4—C5—C6	178.96 (13)	O1—C11—C12—C13	19.9 (2)
C3—C4—C5—C10	−0.5 (2)	C1—C11—C12—C13	−161.07 (12)
C4—C5—C6—C7	−178.55 (13)	C17—C12—C13—C14	−0.2 (2)
C10—C5—C6—C7	0.9 (2)	C11—C12—C13—C14	−178.91 (12)
C5—C6—C7—C8	−0.8 (2)	C12—C13—C14—C15	0.8 (2)
C19—O5—C8—C9	−1.44 (19)	C13—C14—C15—C16	−0.8 (2)
C19—O5—C8—C7	179.73 (12)	C13—C14—C15—C20	178.81 (13)
C6—C7—C8—O5	179.11 (12)	C14—C15—C16—C17	0.2 (2)
C6—C7—C8—C9	0.2 (2)	C20—C15—C16—C17	−179.44 (13)
O5—C8—C9—C10	−178.55 (11)	C15—C16—C17—C12	0.5 (2)
C7—C8—C9—C10	0.2 (2)	C13—C12—C17—C16	−0.5 (2)
C2—C1—C10—C5	0.31 (19)	C11—C12—C17—C16	178.25 (12)
C11—C1—C10—C5	179.92 (11)	C21—O3—C20—O2	−0.9 (2)
C2—C1—C10—C9	−178.35 (12)	C21—O3—C20—C15	178.40 (12)
C11—C1—C10—C9	1.26 (19)	C14—C15—C20—O2	−4.0 (2)
C4—C5—C10—C1	0.33 (18)	C16—C15—C20—O2	175.62 (15)
C6—C5—C10—C1	−179.18 (11)	C14—C15—C20—O3	176.73 (12)
C4—C5—C10—C9	179.04 (11)	C16—C15—C20—O3	−3.64 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19B···O2i	0.98	2.57	3.461 (2)	152
C21—H21A···O1ii	0.98	2.49	3.4446 (19)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19B⋯O2i	0.98	2.57	3.461 (2)	152
C21—H21A⋯O1ii	0.98	2.49	3.4446 (19)	163

Symmetry codes: (i) ; (ii) .