2-(2,7-Dimeth-oxy-1-naphtho-yl)benzoic acid.

In the title compound, C(20)H(16)O(5), the dihedral angle between the naphthalene ring system and the benzene ring is 67.43 (5)°. The bridging carbonyl C-C(=O)-C plane makes dihedral angles of 82.64 (6) and 41.79 (7)°, respectively, with the naphthalene ring system and the benzene ring. The dihedral angle between the carb-oxy O-C(=O)-C plane and the benzene ring is 36.38 (7)° and that between the bridging carbonyl C-C(=O)-C plane and the carb-oxy O-C(=O)-C plane is 51.88 (8)°. The crystal structure is stabilized by inter-molecular O-H⋯O and C-H⋯O hydrogen-bonding inter-actions. An intra-molecular C-H⋯O hydrogen bond occurs between a naphthalene H atom and the carbonyl O atom of the carb-oxy group.

Related literature

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

Experimental

Crystal data

C20H16O5

M = 336.33

Monoclinic,

a = 10.8311 (2) Å

b = 10.61451 (19) Å

c = 15.4492 (3) Å

β = 111.728 (1)°

V = 1649.95 (5) Å3

Z = 4

Cu Kα radiation

μ = 0.81 mm−1

T = 296 K

0.60 × 0.60 × 0.30 mm

Data collection

Rigaku R-AXIS- APID diffractometer

Absorption correction: multi-scan (NUMABS; Higashi, 1999 ▶) T min = 0.711, T max = 0.785

29727 measured reflections

3023 independent reflections

2710 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.095

S = 1.04

3023 reflections

233 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.12 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/S1600536810006847/om2323sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810006847/om2323Isup2.hkl

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

C20H16O5	F(000) = 704
Mr = 336.33	Dx = 1.354 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2ybc	Cell parameters from 26822 reflections
a = 10.8311 (2) Å	θ = 3.1–68.2°
b = 10.61451 (19) Å	µ = 0.81 mm−1
c = 15.4492 (3) Å	T = 296 K
β = 111.728 (1)°	Block, colorless
V = 1649.95 (5) Å3	0.60 × 0.60 × 0.30 mm
Z = 4

Rigaku R-AXIS- APID diffractometer	3023 independent reflections
Radiation source: rotating anode	2710 reflections with I > 2σ(I)
graphite	Rint = 0.028
Detector resolution: 10.00 pixels mm-1	θmax = 68.2°, θmin = 4.4°
ω scans	h = −13→13
Absorption correction: multi-scan (NUMABS; Higashi, 1999)	k = −12→12
Tmin = 0.711, Tmax = 0.785	l = −18→18
29727 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)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.095	w = 1/[σ2(Fo2) + (0.0481P)2 + 0.2862P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
3023 reflections	Δρmax = 0.16 e Å−3
233 parameters	Δρmin = −0.11 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: 0.0021 (3)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.40529 (9)	0.47494 (10)	0.24166 (7)	0.0630 (3)
O2	0.36166 (9)	0.19907 (10)	0.24736 (6)	0.0647 (3)
O3	0.54599 (9)	0.15634 (11)	0.36707 (7)	0.0709 (3)
H1	0.5589 (19)	0.100 (2)	0.3272 (14)	0.104 (6)*
O4	0.30544 (10)	0.73160 (9)	0.28563 (8)	0.0726 (3)
O5	−0.05580 (10)	0.17144 (10)	0.06622 (8)	0.0725 (3)
C1	0.18889 (11)	0.54939 (12)	0.21895 (8)	0.0487 (3)
C2	0.18877 (13)	0.67861 (13)	0.22803 (10)	0.0580 (3)
C3	0.07232 (16)	0.74830 (15)	0.18184 (12)	0.0706 (4)
H3	0.0716	0.8349	0.1906	0.085*
C4	−0.03897 (15)	0.68890 (15)	0.12452 (11)	0.0707 (4)
H4	−0.1149	0.7362	0.0937	0.085*
C5	−0.04262 (13)	0.55796 (14)	0.11051 (9)	0.0590 (3)
C6	−0.15566 (13)	0.49476 (17)	0.04818 (11)	0.0711 (4)
H6	−0.2311	0.5412	0.0148	0.085*
C7	−0.15665 (14)	0.36879 (17)	0.03601 (11)	0.0710 (4)
H7	−0.2324	0.3292	−0.0048	0.085*
C8	−0.04226 (12)	0.29720 (14)	0.08549 (9)	0.0576 (3)
C9	0.06985 (11)	0.35343 (12)	0.14630 (9)	0.0505 (3)
H9	0.1442	0.3050	0.1787	0.061*
C10	0.07285 (11)	0.48552 (12)	0.16004 (8)	0.0495 (3)
C11	0.31457 (11)	0.47747 (11)	0.27012 (8)	0.0447 (3)
C12	0.33101 (10)	0.41688 (11)	0.36061 (7)	0.0409 (3)
C13	0.40131 (10)	0.30406 (11)	0.39141 (7)	0.0402 (3)
C14	0.43259 (12)	0.26655 (13)	0.48298 (8)	0.0511 (3)
H14	0.4795	0.1921	0.5037	0.061*
C15	0.39508 (14)	0.33816 (15)	0.54409 (9)	0.0605 (4)
H15	0.4171	0.3121	0.6055	0.073*
C16	0.32540 (13)	0.44760 (14)	0.51365 (9)	0.0607 (4)
H16	0.3004	0.4960	0.5546	0.073*
C17	0.29207 (12)	0.48650 (12)	0.42223 (9)	0.0523 (3)
H17	0.2431	0.5600	0.4019	0.063*
C18	0.43300 (11)	0.21726 (11)	0.32640 (7)	0.0424 (3)
C19	0.32145 (18)	0.86387 (15)	0.28282 (13)	0.0792 (5)
H19A	0.4114	0.8861	0.3201	0.095*
H19B	0.2620	0.9052	0.3069	0.095*
H19C	0.3017	0.8900	0.2196	0.095*
C20	0.05113 (17)	0.09279 (16)	0.11674 (13)	0.0798 (5)
H20A	0.0300	0.0072	0.0966	0.096*
H20B	0.0671	0.0990	0.1820	0.096*
H20C	0.1293	0.1185	0.1061	0.096*

	U11	U22	U33	U12	U13	U23
O1	0.0532 (5)	0.0731 (6)	0.0744 (6)	0.0134 (4)	0.0372 (5)	0.0261 (5)
O2	0.0577 (5)	0.0842 (7)	0.0423 (5)	0.0184 (5)	0.0068 (4)	−0.0127 (4)
O3	0.0549 (5)	0.0910 (8)	0.0539 (5)	0.0303 (5)	0.0051 (4)	−0.0173 (5)
O4	0.0693 (6)	0.0470 (5)	0.0925 (8)	−0.0002 (5)	0.0194 (6)	0.0074 (5)
O5	0.0589 (6)	0.0676 (6)	0.0757 (7)	−0.0136 (5)	0.0073 (5)	0.0077 (5)
C1	0.0445 (6)	0.0497 (7)	0.0544 (7)	0.0074 (5)	0.0212 (5)	0.0128 (5)
C2	0.0566 (8)	0.0524 (7)	0.0659 (8)	0.0054 (6)	0.0238 (6)	0.0107 (6)
C3	0.0750 (10)	0.0527 (8)	0.0863 (10)	0.0201 (7)	0.0326 (8)	0.0185 (7)
C4	0.0591 (8)	0.0723 (10)	0.0796 (10)	0.0264 (7)	0.0245 (8)	0.0246 (8)
C5	0.0472 (7)	0.0696 (9)	0.0616 (8)	0.0142 (6)	0.0216 (6)	0.0198 (6)
C6	0.0434 (7)	0.0907 (12)	0.0713 (9)	0.0153 (7)	0.0121 (6)	0.0229 (8)
C7	0.0430 (7)	0.0918 (12)	0.0670 (9)	−0.0025 (7)	0.0073 (6)	0.0146 (8)
C8	0.0459 (7)	0.0673 (8)	0.0574 (7)	−0.0049 (6)	0.0165 (6)	0.0115 (6)
C9	0.0398 (6)	0.0567 (7)	0.0531 (7)	0.0037 (5)	0.0151 (5)	0.0141 (5)
C10	0.0411 (6)	0.0580 (7)	0.0518 (6)	0.0067 (5)	0.0200 (5)	0.0138 (5)
C11	0.0402 (6)	0.0435 (6)	0.0520 (6)	−0.0009 (5)	0.0190 (5)	0.0036 (5)
C12	0.0340 (5)	0.0447 (6)	0.0449 (6)	−0.0026 (4)	0.0154 (4)	−0.0013 (5)
C13	0.0345 (5)	0.0464 (6)	0.0388 (5)	−0.0007 (4)	0.0125 (4)	−0.0013 (4)
C14	0.0502 (7)	0.0599 (7)	0.0410 (6)	0.0052 (6)	0.0143 (5)	0.0036 (5)
C15	0.0610 (8)	0.0820 (10)	0.0397 (6)	0.0000 (7)	0.0200 (6)	−0.0030 (6)
C16	0.0622 (8)	0.0724 (9)	0.0560 (7)	−0.0029 (7)	0.0319 (6)	−0.0168 (6)
C17	0.0493 (7)	0.0511 (7)	0.0623 (7)	0.0009 (5)	0.0274 (6)	−0.0056 (6)
C18	0.0383 (5)	0.0476 (6)	0.0398 (6)	0.0030 (5)	0.0128 (5)	0.0003 (5)
C19	0.0928 (12)	0.0515 (8)	0.0992 (12)	−0.0041 (8)	0.0423 (10)	0.0056 (8)
C20	0.0753 (10)	0.0634 (9)	0.0870 (11)	−0.0022 (8)	0.0142 (8)	−0.0008 (8)

O1—C11	1.2163 (13)	C8—C9	1.3670 (18)
O2—C18	1.1945 (13)	C9—C10	1.4166 (18)
O3—C18	1.3195 (14)	C9—H9	0.9300
O3—H1	0.91 (2)	C11—C12	1.4885 (16)
O4—C2	1.3684 (17)	C12—C17	1.3884 (16)
O4—C19	1.4173 (18)	C12—C13	1.4042 (16)
O5—C8	1.3637 (18)	C13—C14	1.3856 (16)
O5—C20	1.4065 (19)	C13—C18	1.4935 (15)
C1—C2	1.3788 (19)	C14—C15	1.3849 (18)
C1—C10	1.4215 (17)	C14—H14	0.9300
C1—C11	1.5046 (15)	C15—C16	1.370 (2)
C2—C3	1.4074 (19)	C15—H15	0.9300
C3—C4	1.358 (2)	C16—C17	1.3850 (19)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.405 (2)	C17—H17	0.9300
C4—H4	0.9300	C19—H19A	0.9600
C5—C6	1.415 (2)	C19—H19B	0.9600
C5—C10	1.4256 (16)	C19—H19C	0.9600
C6—C7	1.350 (2)	C20—H20A	0.9600
C6—H6	0.9300	C20—H20B	0.9600
C7—C8	1.4126 (19)	C20—H20C	0.9600
C7—H7	0.9300
C18—O3—H1	110.5 (12)	C12—C11—C1	118.89 (9)
C2—O4—C19	118.76 (12)	C17—C12—C13	119.07 (10)
C8—O5—C20	117.39 (11)	C17—C12—C11	116.93 (11)
C2—C1—C10	120.37 (11)	C13—C12—C11	123.23 (10)
C2—C1—C11	119.08 (11)	C14—C13—C12	119.21 (10)
C10—C1—C11	120.53 (11)	C14—C13—C18	118.63 (10)
O4—C2—C1	116.08 (12)	C12—C13—C18	121.94 (9)
O4—C2—C3	123.52 (13)	C15—C14—C13	121.04 (12)
C1—C2—C3	120.37 (14)	C15—C14—H14	119.5
C4—C3—C2	119.94 (14)	C13—C14—H14	119.5
C4—C3—H3	120.0	C16—C15—C14	119.65 (12)
C2—C3—H3	120.0	C16—C15—H15	120.2
C3—C4—C5	121.82 (13)	C14—C15—H15	120.2
C3—C4—H4	119.1	C15—C16—C17	120.35 (12)
C5—C4—H4	119.1	C15—C16—H16	119.8
C4—C5—C6	122.79 (13)	C17—C16—H16	119.8
C4—C5—C10	118.80 (13)	C16—C17—C12	120.65 (12)
C6—C5—C10	118.40 (13)	C16—C17—H17	119.7
C7—C6—C5	121.64 (13)	C12—C17—H17	119.7
C7—C6—H6	119.2	O2—C18—O3	122.85 (11)
C5—C6—H6	119.2	O2—C18—C13	124.36 (10)
C6—C7—C8	119.83 (14)	O3—C18—C13	112.69 (9)
C6—C7—H7	120.1	O4—C19—H19A	109.5
C8—C7—H7	120.1	O4—C19—H19B	109.5
O5—C8—C9	125.01 (12)	H19A—C19—H19B	109.5
O5—C8—C7	113.99 (13)	O4—C19—H19C	109.5
C9—C8—C7	121.00 (14)	H19A—C19—H19C	109.5
C8—C9—C10	120.03 (11)	H19B—C19—H19C	109.5
C8—C9—H9	120.0	O5—C20—H20A	109.5
C10—C9—H9	120.0	O5—C20—H20B	109.5
C9—C10—C1	122.26 (10)	H20A—C20—H20B	109.5
C9—C10—C5	119.11 (12)	O5—C20—H20C	109.5
C1—C10—C5	118.59 (12)	H20A—C20—H20C	109.5
O1—C11—C12	119.88 (10)	H20B—C20—H20C	109.5
O1—C11—C1	121.07 (10)
C19—O4—C2—C1	166.64 (13)	C6—C5—C10—C9	−0.91 (18)
C19—O4—C2—C3	−15.3 (2)	C4—C5—C10—C1	−2.41 (18)
C10—C1—C2—O4	−179.44 (11)	C6—C5—C10—C1	176.71 (12)
C11—C1—C2—O4	−1.13 (18)	C2—C1—C11—O1	−77.60 (16)
C10—C1—C2—C3	2.4 (2)	C10—C1—C11—O1	100.70 (14)
C11—C1—C2—C3	−179.30 (12)	C2—C1—C11—C12	97.80 (14)
O4—C2—C3—C4	178.89 (14)	C10—C1—C11—C12	−83.90 (14)
C1—C2—C3—C4	−3.1 (2)	O1—C11—C12—C17	132.79 (12)
C2—C3—C4—C5	1.0 (2)	C1—C11—C12—C17	−42.67 (15)
C3—C4—C5—C6	−177.30 (14)	O1—C11—C12—C13	−37.07 (17)
C3—C4—C5—C10	1.8 (2)	C1—C11—C12—C13	147.48 (11)
C4—C5—C6—C7	−179.97 (15)	C17—C12—C13—C14	−1.43 (16)
C10—C5—C6—C7	0.9 (2)	C11—C12—C13—C14	168.22 (11)
C5—C6—C7—C8	−0.7 (2)	C17—C12—C13—C18	173.01 (10)
C20—O5—C8—C9	3.8 (2)	C11—C12—C13—C18	−17.34 (16)
C20—O5—C8—C7	−176.41 (14)	C12—C13—C14—C15	0.31 (18)
C6—C7—C8—O5	−179.36 (14)	C18—C13—C14—C15	−174.32 (11)
C6—C7—C8—C9	0.4 (2)	C13—C14—C15—C16	0.3 (2)
O5—C8—C9—C10	179.34 (12)	C14—C15—C16—C17	0.2 (2)
C7—C8—C9—C10	−0.4 (2)	C15—C16—C17—C12	−1.4 (2)
C8—C9—C10—C1	−176.87 (11)	C13—C12—C17—C16	1.96 (17)
C8—C9—C10—C5	0.67 (18)	C11—C12—C17—C16	−168.33 (11)
C2—C1—C10—C9	177.90 (12)	C14—C13—C18—O2	139.14 (13)
C11—C1—C10—C9	−0.38 (17)	C12—C13—C18—O2	−35.33 (18)
C2—C1—C10—C5	0.35 (17)	C14—C13—C18—O3	−37.23 (15)
C11—C1—C10—C5	−177.93 (11)	C12—C13—C18—O3	148.30 (11)
C4—C5—C10—C9	179.96 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1···O1i	0.91 (2)	1.83 (2)	2.7320 (15)	173.4 (19)
C7—H7···O3ii	0.93	2.49	3.3215 (19)	150
C15—H15···O2iii	0.93	2.48	3.3152 (16)	149
C17—H17···O5iv	0.93	2.55	3.2821 (18)	136
C9—H9···O2	0.93	2.47	3.3850 (16)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1⋯O1i	0.91 (2)	1.83 (2)	2.7320 (15)	173.4 (19)
C7—H7⋯O3ii	0.93	2.49	3.3215 (19)	150
C15—H15⋯O2iii	0.93	2.48	3.3152 (16)	149
C17—H17⋯O5iv	0.93	2.55	3.2821 (18)	136
C9—H9⋯O2	0.93	2.47	3.3850 (16)	169

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