4-[(2-Hydr-oxy-1-naphth-yl)methyl-idene-amino]benzoic acid.

The mol-ecule of the title compound, C(18)H(13)NO(3), is almost planar, the dihedral angle between the naphthalene and benzene ring systems being 4.04 (6)°. The mol-ecular conformation and packing are stabilized by intra-molecular O-H⋯N and inter-molecular O-H⋯O and C-H⋯O inter-actions.

Related literature

For background, see: Asiri & Badahdah (2007 ▶).

Experimental

Crystal data

C18H13NO3

M = 291.29

Monoclinic,

a = 14.7490 (12) Å

b = 4.9850 (4) Å

c = 36.750 (3) Å

β = 91.305 (1)°

V = 2701.3 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 150 (2) K

0.31 × 0.19 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.970, T max = 0.991

13445 measured reflections

3520 independent reflections

2761 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.145

S = 1.07

3520 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.59 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808006107/hb2705sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808006107/hb2705Isup2.hkl

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

C18H13NO3	F000 = 1216
Mr = 291.29	Dx = 1.433 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71069 Å
Hall symbol: -C 2yc	Cell parameters from 3973 reflections
a = 14.7490 (12) Å	θ = 2.2–28.8º
b = 4.9850 (4) Å	µ = 0.10 mm−1
c = 36.750 (3) Å	T = 150 (2) K
β = 91.305 (1)º	Lath, orange
V = 2701.3 (4) Å3	0.31 × 0.19 × 0.09 mm
Z = 8

Bruker APEXII CCD diffractometer	3520 independent reflections
Radiation source: sealed tube	2761 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.031
T = 150(2) K	θmax = 28.9º
φ and ω scans	θmin = 2.2º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −20→19
Tmin = 0.970, Tmax = 0.991	k = −6→6
13445 measured reflections	l = −49→49

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)] = 0.050	H-atom parameters constrained
wR(F2) = 0.145	w = 1/[σ2(Fo2) + (0.0792P)2 + 1.0642P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
3520 reflections	Δρmax = 0.59 e Å−3
210 parameters	Δρmin = −0.33 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.11588 (7)	0.8430 (3)	0.11623 (4)	0.0398 (4)
O2	0.39188 (7)	−0.3435 (2)	0.00066 (3)	0.0295 (3)
O3	0.52323 (6)	−0.2551 (2)	0.03002 (3)	0.0277 (3)
N1	0.26607 (8)	0.6069 (2)	0.10400 (3)	0.0232 (3)
C1	0.15748 (10)	0.9891 (3)	0.13926 (4)	0.0293 (4)
C2	0.10809 (11)	1.1871 (4)	0.15946 (5)	0.0387 (5)
C3	0.14890 (11)	1.3471 (3)	0.18415 (5)	0.0368 (5)
C4	0.24458 (10)	1.3336 (3)	0.19194 (4)	0.0273 (4)
C5	0.28528 (12)	1.5100 (3)	0.21737 (4)	0.0333 (4)
C6	0.37653 (13)	1.5035 (3)	0.22449 (4)	0.0367 (5)
C7	0.43000 (12)	1.3207 (3)	0.20591 (5)	0.0382 (5)
C8	0.39165 (11)	1.1460 (3)	0.18077 (4)	0.0328 (4)
C9	0.29754 (10)	1.1446 (3)	0.17322 (4)	0.0235 (4)
C10	0.25387 (9)	0.9658 (3)	0.14694 (4)	0.0227 (3)
C11	0.30277 (9)	0.7702 (3)	0.12869 (4)	0.0222 (3)
C12	0.31172 (9)	0.4082 (3)	0.08444 (4)	0.0216 (3)
C13	0.26106 (9)	0.2595 (3)	0.05899 (4)	0.0237 (4)
C14	0.30229 (9)	0.0589 (3)	0.03908 (4)	0.0236 (4)
C15	0.39461 (9)	0.0041 (3)	0.04452 (4)	0.0212 (3)
C16	0.44479 (9)	0.1537 (3)	0.07000 (4)	0.0237 (4)
C17	0.40437 (9)	0.3544 (3)	0.08974 (4)	0.0237 (4)
C18	0.44065 (9)	−0.2106 (3)	0.02406 (4)	0.0224 (3)
HO1	0.15250	0.74990	0.10550	0.0600*
H2	0.04600	1.20430	0.15520	0.053 (6)*
HO2	0.42310	−0.45920	−0.00880	0.0440*
H3	0.11410	1.47080	0.19660	0.046 (5)*
H5	0.24950	1.63300	0.22950	0.041 (5)*
H6	0.40270	1.61950	0.24150	0.045 (5)*
H7	0.49230	1.31630	0.21050	0.058 (6)*
H8	0.42870	1.02670	0.16860	0.037 (5)*
H11	0.36440	0.75340	0.13410	0.0270*
H13	0.19960	0.29500	0.05540	0.0280*
H14	0.26850	−0.03930	0.02210	0.031 (4)*
H16	0.50620	0.11760	0.07370	0.022 (4)*
H17	0.43850	0.45380	0.10650	0.031 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0220 (5)	0.0457 (7)	0.0513 (7)	0.0052 (5)	−0.0055 (5)	−0.0177 (6)
O2	0.0250 (5)	0.0288 (5)	0.0348 (6)	−0.0002 (4)	0.0003 (4)	−0.0125 (4)
O3	0.0212 (5)	0.0280 (5)	0.0340 (5)	0.0019 (4)	0.0017 (4)	−0.0052 (4)
N1	0.0220 (5)	0.0239 (6)	0.0238 (6)	0.0009 (4)	0.0003 (4)	−0.0034 (4)
C1	0.0236 (7)	0.0307 (7)	0.0336 (8)	0.0035 (6)	0.0012 (6)	−0.0026 (6)
C2	0.0244 (7)	0.0432 (9)	0.0485 (10)	0.0085 (7)	0.0031 (7)	−0.0090 (8)
C3	0.0340 (8)	0.0371 (8)	0.0396 (9)	0.0111 (7)	0.0078 (7)	−0.0078 (7)
C4	0.0359 (8)	0.0237 (7)	0.0224 (7)	0.0030 (6)	0.0047 (5)	0.0017 (5)
C5	0.0487 (9)	0.0257 (7)	0.0257 (7)	0.0055 (7)	0.0049 (6)	−0.0032 (6)
C6	0.0533 (10)	0.0281 (7)	0.0285 (8)	−0.0041 (7)	−0.0049 (7)	−0.0053 (6)
C7	0.0379 (9)	0.0361 (8)	0.0402 (9)	−0.0015 (7)	−0.0091 (7)	−0.0079 (7)
C8	0.0319 (8)	0.0295 (7)	0.0368 (8)	0.0039 (6)	−0.0038 (6)	−0.0084 (6)
C9	0.0287 (7)	0.0204 (6)	0.0213 (6)	0.0014 (5)	0.0020 (5)	0.0011 (5)
C10	0.0233 (6)	0.0226 (6)	0.0222 (6)	0.0009 (5)	0.0012 (5)	0.0000 (5)
C11	0.0209 (6)	0.0230 (6)	0.0228 (6)	0.0005 (5)	0.0000 (5)	0.0001 (5)
C12	0.0219 (6)	0.0215 (6)	0.0214 (6)	0.0000 (5)	0.0016 (5)	−0.0002 (5)
C13	0.0182 (6)	0.0264 (7)	0.0264 (7)	0.0009 (5)	−0.0023 (5)	−0.0018 (5)
C14	0.0223 (6)	0.0246 (6)	0.0237 (7)	−0.0021 (5)	−0.0022 (5)	−0.0031 (5)
C15	0.0206 (6)	0.0210 (6)	0.0221 (6)	−0.0017 (5)	0.0018 (5)	−0.0010 (5)
C16	0.0188 (6)	0.0261 (7)	0.0263 (7)	−0.0006 (5)	−0.0001 (5)	−0.0033 (5)
C17	0.0210 (6)	0.0258 (7)	0.0243 (6)	−0.0020 (5)	−0.0016 (5)	−0.0048 (5)
C18	0.0223 (6)	0.0214 (6)	0.0235 (6)	−0.0025 (5)	0.0027 (5)	−0.0013 (5)

O1—C1	1.265 (2)	C12—C17	1.4018 (19)
O2—C18	1.2914 (18)	C12—C13	1.397 (2)
O3—C18	1.2524 (16)	C13—C14	1.388 (2)
O1—HO1	0.8200	C14—C15	1.3987 (19)
O2—HO2	0.8200	C15—C16	1.396 (2)
N1—C12	1.4047 (18)	C15—C18	1.482 (2)
N1—C11	1.3254 (18)	C16—C17	1.379 (2)
C1—C2	1.442 (2)	C2—H2	0.9300
C1—C10	1.448 (2)	C3—H3	0.9300
C2—C3	1.341 (3)	C5—H5	0.9300
C3—C4	1.435 (2)	C6—H6	0.9300
C4—C9	1.413 (2)	C7—H7	0.9300
C4—C5	1.408 (2)	C8—H8	0.9300
C5—C6	1.366 (3)	C11—H11	0.9300
C6—C7	1.394 (2)	C13—H13	0.9300
C7—C8	1.381 (2)	C14—H14	0.9300
C8—C9	1.409 (2)	C16—H16	0.9300
C9—C10	1.454 (2)	C17—H17	0.9300
C10—C11	1.394 (2)
C1—O1—HO1	109.00	C14—C15—C18	121.63 (13)
C18—O2—HO2	109.00	C15—C16—C17	120.76 (13)
C11—N1—C12	126.19 (12)	C12—C17—C16	119.83 (13)
O1—C1—C2	119.70 (14)	O3—C18—C15	119.63 (13)
C2—C1—C10	117.37 (13)	O2—C18—O3	123.39 (13)
O1—C1—C10	122.92 (14)	O2—C18—C15	116.99 (12)
C1—C2—C3	122.09 (15)	C1—C2—H2	119.00
C2—C3—C4	122.11 (15)	C3—C2—H2	119.00
C3—C4—C9	119.09 (14)	C2—C3—H3	119.00
C3—C4—C5	120.38 (14)	C4—C3—H3	119.00
C5—C4—C9	120.52 (14)	C4—C5—H5	119.00
C4—C5—C6	121.06 (14)	C6—C5—H5	119.00
C5—C6—C7	119.19 (15)	C5—C6—H6	120.00
C6—C7—C8	120.81 (16)	C7—C6—H6	120.00
C7—C8—C9	121.42 (14)	C6—C7—H7	120.00
C4—C9—C10	119.40 (13)	C8—C7—H7	120.00
C4—C9—C8	116.99 (13)	C7—C8—H8	119.00
C8—C9—C10	123.59 (13)	C9—C8—H8	119.00
C1—C10—C11	118.61 (13)	N1—C11—H11	118.00
C1—C10—C9	119.90 (13)	C10—C11—H11	118.00
C9—C10—C11	121.48 (12)	C12—C13—H13	120.00
N1—C11—C10	123.46 (12)	C14—C13—H13	120.00
N1—C12—C17	122.74 (13)	C13—C14—H14	120.00
C13—C12—C17	119.77 (13)	C15—C14—H14	120.00
N1—C12—C13	117.49 (12)	C15—C16—H16	120.00
C12—C13—C14	120.09 (12)	C17—C16—H16	120.00
C13—C14—C15	120.15 (13)	C12—C17—H17	120.00
C14—C15—C16	119.41 (13)	C16—C17—H17	120.00
C16—C15—C18	118.96 (12)
C12—N1—C11—C10	179.29 (14)	C7—C8—C9—C10	179.74 (15)
C11—N1—C12—C13	−178.82 (14)	C4—C9—C10—C1	2.2 (2)
C11—N1—C12—C17	1.6 (2)	C4—C9—C10—C11	−177.85 (14)
O1—C1—C2—C3	−179.95 (18)	C8—C9—C10—C1	−176.23 (14)
C10—C1—C2—C3	0.8 (3)	C8—C9—C10—C11	3.8 (2)
O1—C1—C10—C9	178.67 (15)	C1—C10—C11—N1	1.4 (2)
O1—C1—C10—C11	−1.3 (2)	C9—C10—C11—N1	−178.55 (14)
C2—C1—C10—C9	−2.1 (2)	N1—C12—C13—C14	−179.43 (13)
C2—C1—C10—C11	177.93 (15)	C17—C12—C13—C14	0.1 (2)
C1—C2—C3—C4	0.5 (3)	N1—C12—C17—C16	179.04 (13)
C2—C3—C4—C5	178.31 (16)	C13—C12—C17—C16	−0.5 (2)
C2—C3—C4—C9	−0.5 (2)	C12—C13—C14—C15	0.3 (2)
C3—C4—C5—C6	−178.57 (15)	C13—C14—C15—C16	−0.3 (2)
C9—C4—C5—C6	0.2 (2)	C13—C14—C15—C18	179.30 (14)
C3—C4—C9—C8	177.61 (14)	C14—C15—C16—C17	−0.1 (2)
C3—C4—C9—C10	−0.9 (2)	C18—C15—C16—C17	−179.67 (14)
C5—C4—C9—C8	−1.1 (2)	C14—C15—C18—O2	0.7 (2)
C5—C4—C9—C10	−179.65 (14)	C14—C15—C18—O3	−179.25 (14)
C4—C5—C6—C7	0.7 (2)	C16—C15—C18—O2	−179.75 (13)
C5—C6—C7—C8	−0.5 (2)	C16—C15—C18—O3	0.3 (2)
C6—C7—C8—C9	−0.5 (2)	C15—C16—C17—C12	0.5 (2)
C7—C8—C9—C4	1.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—HO1···N1	0.82	1.82	2.5572 (16)	148
O2—HO2···O3i	0.82	1.81	2.6281 (14)	171
C14—H14···O2ii	0.93	2.56	3.3611 (17)	145
C16—H16···O1iii	0.93	2.49	3.1542 (19)	128

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—HO1⋯N1	0.82	1.82	2.5572 (16)	148
O2—HO2⋯O3i	0.82	1.81	2.6281 (14)	171
C14—H14⋯O2ii	0.93	2.56	3.3611 (17)	145
C16—H16⋯O1iii	0.93	2.49	3.1542 (19)	128

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