3-[(2-Oxo-1-naphthylidene)methyl­amino]­benzoic acid

The title compound, C₁₈H₁₃NO₃, exists as a keto­amino tautomer implying a fairly short N—H...O intramolecular hydrogen bond between the 2-naphthalenone and amino moieties [N...O 2.531 (3) Å] which is enhanced by the π-electron delocalization effect. The naphthald­imine and 3-carboxy­phenyl fragments are inclined at an angle of 4.41 (7)°, so the mol­ecule is almost planar. The mol­ecules are connected by intermolecular O—H...O hydrogen bonds between the carboxy and keto O atoms, forming infinite chains around the twofold screw axes parallel to b.

Computing details

Data collection: STADI4 (Stoe & Cie, 1995); cell refinement: STADI4; data reduction: X-RED (Stoe & Cie, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON98 (Spek, 1998); software used to prepare material for publication: SHELXL97.

(I)

Crystal data

C18H13NO3	F(000) = 608
Mr = 291.29	Dx = 1.423 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.665 (2) Å	Cell parameters from 28 reflections
b = 7.4718 (11) Å	θ = 9.1–16.9°
c = 16.2794 (15) Å	µ = 0.10 mm^−1
β = 106.666 (14)°	T = 293 K
V = 1359.3 (3) Å^3	Plate, pale orange
Z = 4	0.55 × 0.24 × 0.04 mm

Data collection

Philips PW1100 upgraded by Stoe diffractometer	Rint = 0.014
Radiation source: fine-focus sealed tube	θmax = 26.9°, θmin = 3.0°
Graphite monochromator	h = −14→14
ω scan	k = 0→9
2968 measured reflections	l = 0→20
2866 independent reflections	3 standard reflections every 90 min
1374 reflections with I > 2σ(I)	intensity decay: 6.8%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	Hydrogen site location: d
wR(F^2) = 0.117	All H-atom parameters refined
S = 0.94	Calculated w = 1/[σ^2(Fo^2) + (0.0551P)^2] where P = (Fo^2 + 2Fc^2)/3
2866 reflections	(Δ/σ)max < 0.001
251 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.17 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.79030 (14)	0.0436 (2)	0.47774 (9)	0.0548 (5)
O2	0.24254 (14)	0.4589 (3)	0.18395 (10)	0.0564 (5)
O3	0.42353 (15)	0.3607 (3)	0.18791 (9)	0.0614 (5)
N1	0.59994 (16)	0.1765 (3)	0.49675 (11)	0.0388 (5)
C1	0.75524 (17)	0.0632 (3)	0.61407 (12)	0.0337 (5)
C2	0.8261 (2)	0.0117 (3)	0.55899 (13)	0.0396 (5)
C3	0.9375 (2)	−0.0785 (3)	0.59532 (15)	0.0463 (6)
C4	0.9766 (2)	−0.1127 (3)	0.67963 (15)	0.0446 (6)
C5	0.9109 (2)	−0.0626 (3)	0.73771 (13)	0.0387 (5)
C6	0.9548 (2)	−0.1027 (3)	0.82586 (15)	0.0491 (6)
C7	0.8918 (2)	−0.0541 (4)	0.88105 (16)	0.0559 (7)
C8	0.7835 (2)	0.0347 (4)	0.85081 (15)	0.0547 (7)
C9	0.7373 (2)	0.0737 (3)	0.76472 (13)	0.0453 (6)
C10	0.8001 (2)	0.0263 (3)	0.70633 (12)	0.0349 (5)
C11	0.6442 (2)	0.1436 (3)	0.57941 (13)	0.0349 (5)
C12	0.4908 (2)	0.2591 (3)	0.45271 (12)	0.0338 (5)
C13	0.4710 (2)	0.2867 (3)	0.36516 (12)	0.0349 (5)
C14	0.3664 (2)	0.3670 (3)	0.31713 (12)	0.0340 (5)
C15	0.2809 (2)	0.4187 (3)	0.35610 (13)	0.0389 (6)
C16	0.3012 (2)	0.3900 (3)	0.44310 (14)	0.0415 (6)
C17	0.4052 (2)	0.3117 (3)	0.49221 (14)	0.0374 (5)
C18	0.3484 (2)	0.3942 (3)	0.22361 (13)	0.0390 (5)
H3	0.986 (2)	−0.108 (3)	0.5589 (15)	0.054 (7)*
H4	1.050 (2)	−0.176 (3)	0.7008 (14)	0.047 (6)*
H6	1.034 (2)	−0.171 (4)	0.8489 (15)	0.062 (7)*
H7	0.923 (2)	−0.087 (3)	0.9400 (17)	0.062 (8)*
H8	0.732 (2)	0.069 (3)	0.8882 (16)	0.067 (8)*
H9	0.658 (2)	0.132 (3)	0.7449 (14)	0.051 (7)*
H11	0.597 (2)	0.175 (3)	0.6147 (14)	0.047 (6)*
H13	0.529 (2)	0.251 (3)	0.3374 (13)	0.040 (6)*
H15	0.212 (2)	0.468 (3)	0.3224 (14)	0.045 (6)*
H16	0.241 (2)	0.424 (3)	0.4698 (15)	0.062 (7)*
H17	0.4195 (17)	0.295 (3)	0.5528 (14)	0.041 (6)*
H1N	0.651 (2)	0.141 (3)	0.4676 (14)	0.050 (7)*
H2O	0.235 (3)	0.482 (4)	0.127 (2)	0.096 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0504 (9)	0.0861 (14)	0.0278 (8)	0.0044 (9)	0.0108 (7)	−0.0027 (8)
O2	0.0507 (10)	0.0880 (15)	0.0287 (9)	0.0164 (10)	0.0086 (8)	0.0137 (9)
O3	0.0488 (9)	0.1066 (15)	0.0312 (8)	0.0050 (10)	0.0155 (8)	0.0041 (9)
N1	0.0368 (10)	0.0498 (13)	0.0286 (9)	−0.0004 (9)	0.0072 (8)	0.0000 (9)
C1	0.0355 (11)	0.0357 (12)	0.0271 (10)	−0.0064 (10)	0.0043 (9)	−0.0022 (9)
C2	0.0412 (12)	0.0490 (14)	0.0285 (11)	−0.0076 (11)	0.0099 (10)	−0.0069 (10)
C3	0.0396 (13)	0.0564 (17)	0.0449 (14)	−0.0009 (12)	0.0156 (11)	−0.0043 (12)
C4	0.0340 (13)	0.0498 (15)	0.0461 (14)	0.0015 (11)	0.0051 (11)	0.0002 (12)
C5	0.0388 (12)	0.0367 (13)	0.0363 (11)	−0.0058 (11)	0.0041 (10)	−0.0009 (10)
C6	0.0467 (14)	0.0531 (16)	0.0409 (13)	0.0007 (13)	0.0021 (11)	0.0084 (12)
C7	0.0631 (17)	0.068 (2)	0.0304 (12)	0.0027 (15)	0.0030 (12)	0.0097 (12)
C8	0.0598 (16)	0.072 (2)	0.0323 (12)	0.0044 (15)	0.0132 (12)	0.0040 (12)
C9	0.0470 (14)	0.0561 (16)	0.0316 (12)	0.0048 (12)	0.0093 (10)	−0.0014 (11)
C10	0.0364 (11)	0.0363 (13)	0.0295 (10)	−0.0047 (10)	0.0053 (9)	−0.0003 (9)
C11	0.0375 (12)	0.0400 (13)	0.0252 (10)	−0.0047 (10)	0.0062 (9)	−0.0012 (9)
C12	0.0341 (11)	0.0347 (13)	0.0286 (10)	−0.0057 (10)	0.0026 (9)	−0.0011 (9)
C13	0.0349 (12)	0.0432 (14)	0.0267 (10)	−0.0041 (11)	0.0088 (9)	−0.0028 (10)
C14	0.0371 (11)	0.0351 (12)	0.0281 (10)	−0.0050 (10)	0.0066 (9)	−0.0005 (9)
C15	0.0376 (12)	0.0467 (15)	0.0311 (11)	0.0036 (11)	0.0076 (10)	0.0011 (10)
C16	0.0433 (13)	0.0479 (15)	0.0363 (12)	0.0026 (11)	0.0164 (11)	−0.0025 (11)
C17	0.0439 (13)	0.0433 (14)	0.0255 (11)	−0.0038 (11)	0.0108 (10)	−0.0018 (10)
C18	0.0391 (12)	0.0495 (15)	0.0277 (11)	−0.0047 (11)	0.0086 (10)	−0.0018 (10)

Geometric parameters (Å, º)

O1—C2	1.290 (2)	C13—C14	1.383 (3)
O2—C18	1.311 (3)	C14—C15	1.382 (3)
O3—C18	1.208 (3)	C14—C18	1.490 (3)
N1—C11	1.319 (3)	C15—C16	1.384 (3)
N1—C12	1.411 (3)	C16—C17	1.377 (3)
C1—C11	1.392 (3)	O2—H2O	0.92 (3)
C1—C2	1.435 (3)	N1—H1N	0.90 (2)
C1—C10	1.468 (3)	C3—H3	0.96 (2)
C2—C3	1.433 (3)	C4—H4	0.95 (2)
C3—C4	1.341 (3)	C6—H6	1.03 (3)
C4—C5	1.427 (3)	C7—H7	0.96 (3)
C5—C6	1.411 (3)	C8—H8	1.00 (2)
C5—C10	1.413 (3)	C9—H9	0.99 (2)
C6—C7	1.363 (4)	C11—H11	0.93 (2)
C7—C8	1.386 (4)	C13—H13	0.96 (2)
C8—C9	1.381 (3)	C15—H15	0.91 (2)
C9—C10	1.402 (3)	C16—H16	0.96 (2)
C12—C17	1.390 (3)	C17—H17	0.96 (2)
C12—C13	1.392 (3)
C11—N1—C12	129.2 (2)	C16—C17—C12	118.8 (2)
C11—C1—C2	119.9 (2)	O3—C18—O2	123.4 (2)
C11—C1—C10	120.8 (2)	O3—C18—C14	123.7 (2)
C2—C1—C10	119.3 (2)	O2—C18—C14	113.0 (2)
O1—C2—C3	119.9 (2)	C18—O2—H2O	112 (2)
O1—C2—C1	121.1 (2)	C12—N1—H1N	119.8 (14)
C3—C2—C1	119.0 (2)	C11—N1—H1N	111.0 (14)
C4—C3—C2	120.9 (2)	C2—C3—H3	118.7 (14)
C3—C4—C5	122.6 (2)	C4—C3—H3	120.2 (14)
C6—C5—C10	119.7 (2)	C3—C4—H4	118.2 (14)
C6—C5—C4	120.7 (2)	C5—C4—H4	119.2 (14)
C10—C5—C4	119.6 (2)	C5—C6—H6	120.2 (13)
C7—C6—C5	120.4 (2)	C7—C6—H6	119.3 (13)
C6—C7—C8	120.2 (2)	C6—C7—H7	118.1 (15)
C9—C8—C7	120.8 (3)	C8—C7—H7	121.7 (15)
C8—C9—C10	120.5 (2)	C7—C8—H8	123.4 (14)
C9—C10—C5	118.4 (2)	C9—C8—H8	115.8 (14)
C9—C10—C1	123.0 (2)	C8—C9—H9	118.7 (13)
C5—C10—C1	118.6 (2)	C10—C9—H9	120.8 (13)
N1—C11—C1	122.7 (2)	N1—C11—H11	117.0 (14)
C17—C12—C13	120.1 (2)	C1—C11—H11	120.3 (14)
C17—C12—N1	123.5 (2)	C12—C13—H13	120.7 (13)
C13—C12—N1	116.5 (2)	C14—C13—H13	119.0 (13)
C14—C13—C12	120.2 (2)	C14—C15—H15	117.7 (14)
C15—C14—C13	119.8 (2)	C16—C15—H15	122.8 (14)
C15—C14—C18	121.5 (2)	C15—C16—H16	119.3 (14)
C13—C14—C18	118.7 (2)	C17—C16—H16	119.1 (14)
C14—C15—C16	119.5 (2)	C12—C17—H17	120.2 (13)
C17—C16—C15	121.6 (2)	C16—C17—H17	121.0 (13)
C11—C1—C2—O1	2.2 (3)	C11—C1—C10—C5	177.3 (2)
C10—C1—C2—O1	−179.3 (2)	C2—C1—C10—C5	−1.3 (3)
C11—C1—C2—C3	−177.1 (2)	C12—N1—C11—C1	−178.8 (2)
C10—C1—C2—C3	1.5 (3)	C2—C1—C11—N1	−0.4 (3)
O1—C2—C3—C4	179.9 (2)	C10—C1—C11—N1	−178.9 (2)
C1—C2—C3—C4	−0.9 (3)	C11—N1—C12—C17	−4.2 (4)
C2—C3—C4—C5	0.1 (4)	C11—N1—C12—C13	175.9 (2)
C3—C4—C5—C6	179.4 (2)	C17—C12—C13—C14	0.2 (3)
C3—C4—C5—C10	0.1 (4)	N1—C12—C13—C14	−179.9 (2)
C10—C5—C6—C7	−0.9 (3)	C12—C13—C14—C15	−0.6 (3)
C4—C5—C6—C7	179.8 (2)	C12—C13—C14—C18	−180.0 (2)
C5—C6—C7—C8	0.3 (4)	C13—C14—C15—C16	0.3 (3)
C6—C7—C8—C9	0.6 (4)	C18—C14—C15—C16	179.7 (2)
C7—C8—C9—C10	−0.9 (4)	C14—C15—C16—C17	0.3 (3)
C8—C9—C10—C5	0.3 (3)	C15—C16—C17—C12	−0.6 (3)
C8—C9—C10—C1	179.6 (2)	C13—C12—C17—C16	0.4 (3)
C6—C5—C10—C9	0.6 (3)	N1—C12—C17—C16	−179.5 (2)
C4—C5—C10—C9	179.9 (2)	C15—C14—C18—O3	175.5 (2)
C6—C5—C10—C1	−178.8 (2)	C13—C14—C18—O3	−5.1 (3)
C4—C5—C10—C1	0.5 (3)	C15—C14—C18—O2	−4.2 (3)
C11—C1—C10—C9	−2.1 (3)	C13—C14—C18—O2	175.2 (2)
C2—C1—C10—C9	179.3 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	0.90 (2)	1.74 (2)	2.531 (3)	144.3 (2)
O2—H2O···O1^i	0.92 (3)	1.71 (3)	2.626 (2)	173.7 (3)
C17—H17···O3^ii	0.96 (2)	2.48 (2)	3.386 (3)	158.2 (2)
C15—H15···O2	0.91 (2)	2.38 (2)	2.725 (3)	102.0 (2)

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x, −y+1/2, z+1/2.