3-Methyl-1,4-dioxo-1,4-dihydro-naphthalen-2-yl 4-amino-benzoate.

The crystal structure of the title compound, C(18)H(13)NO(4), the oxidized form of the drug aminaftone used in venous disease therapy, is characterized by the presence of ribbons of hydrogen-bonded mol-ecules parallel to the [111] crystallographic direction and by stacking inter-actions between rings [centroid-centroid distance between quinone rings = 3.684 (3) Å and between amino-benzoate rings = 4.157 (3) Å] along the ribbons.

Related literature

For related literature, see: De Anna et al. (1989 ▶); Martinez et al. (2005 ▶).

Experimental

Crystal data

C18H13NO4

M = 307.29

Triclinic,

a = 7.6217 (6) Å

b = 9.6142 (7) Å

c = 10.6456 (7) Å

α = 101.618 (6)°

β = 110.770 (7)°

γ = 89.019 (6)°

V = 713.18 (10) Å3

Z = 2

Cu Kα radiation

μ = 0.85 mm−1

T = 170 (2) K

0.60 × 0.20 × 0.05 mm

Data collection

Oxford Diffraction Xcalibur PX Ultra CCD diffractometer

Absorption correction: multi-scan (ABSPACK; Oxford Diffraction, 2006 ▶) T min = 0.501, T max = 1.000 (expected range = 0.480–0.959)

6339 measured reflections

2453 independent reflections

1845 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.142

S = 1.12

2453 reflections

215 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.23 e Å−3

Data collection: CrysAlisPro CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlisPro CCD; data reduction: CrysAlisPro RED (Oxford Diffraction, 2006 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808005308/rk2078sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808005308/rk2078Isup2.hkl

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

C18H13NO4	Z = 2
Mr = 307.29	F000 = 320
Triclinic, P1	Dx = 1.431 Mg m−3
Hall symbol: -P 1	Cu Kα radiation λ = 1.54180 Å
a = 7.6217 (6) Å	Cell parameters from 3411 reflections
b = 9.6142 (7) Å	θ = 9.6–53.4º
c = 10.6456 (7) Å	µ = 0.85 mm−1
α = 101.618 (6)º	T = 170 (2) K
β = 110.770 (7)º	Flat prism, red
γ = 89.019 (6)º	0.60 × 0.20 × 0.05 mm
V = 713.18 (10) Å3

Oxford Diffraction Xcalibur PX Ultra CCD diffractometer	2453 independent reflections
Radiation source: Fine–focus sealed tube	1845 reflections with I > 2σ(I)
Monochromator: Oxford Diffraction Enhance ULTRA assembly	Rint = 0.022
Detector resolution: 8.1241 pixels mm-1	θmax = 72.4º
T = 170(2) K	θmin = 4.5º
ω scans	h = −9→9
Absorption correction: multi-scan(ABSPACK; Oxford Diffraction, 2006)	k = −11→11
Tmin = 0.501, Tmax = 1.000	l = −12→12
6339 measured reflections

Refinement on F2	Secondary atom site location: Difmap
Least-squares matrix: Full	Hydrogen site location: Difmap
R[F2 > 2σ(F2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.142	w = 1/[σ2(Fo2) + (0.0941P)2 + 0.0064P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max < 0.001
2453 reflections	Δρmax = 0.17 e Å−3
215 parameters	Δρmin = −0.23 e Å−3
Primary atom site location: Direct	Extinction correction: None

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
C1	0.6680 (2)	1.03157 (16)	0.34314 (16)	0.0361 (4)
C2	0.8411 (2)	1.01124 (16)	0.32984 (16)	0.0373 (4)
H2	0.8613	0.9234	0.2787	0.045*
C3	0.9857 (3)	1.11583 (17)	0.38923 (16)	0.0392 (4)
H3	1.1038	1.0996	0.3791	0.047*
C4	0.9568 (3)	1.24645 (17)	0.46471 (16)	0.0398 (4)
N	1.0987 (3)	1.35138 (17)	0.52199 (17)	0.0508 (4)
H1N	1.083 (3)	1.425 (3)	0.582 (2)	0.061*
H2N	1.225 (4)	1.326 (2)	0.542 (2)	0.061*
C5	0.7833 (3)	1.26644 (17)	0.47801 (17)	0.0449 (5)
H5	0.7624	1.3542	0.5289	0.054*
C6	0.6405 (3)	1.16127 (18)	0.41876 (17)	0.0431 (4)
H6	0.5226	1.1770	0.4294	0.052*
C7	0.5122 (3)	0.92331 (17)	0.27898 (16)	0.0384 (4)
O1	0.57285 (17)	0.79775 (12)	0.22176 (13)	0.0464 (4)
O2	0.35157 (19)	0.93363 (13)	0.27039 (14)	0.0498 (4)
C8	0.4401 (2)	0.68767 (16)	0.14533 (17)	0.0377 (4)
C9	0.4125 (2)	0.58405 (18)	0.22396 (17)	0.0386 (4)
O3	0.48719 (18)	0.60587 (14)	0.34797 (12)	0.0497 (4)
C10	0.2922 (2)	0.45428 (17)	0.14241 (18)	0.0388 (4)
C11	0.2663 (3)	0.3494 (2)	0.2090 (2)	0.0498 (5)
H11	0.3227	0.3623	0.3060	0.060*
C12	0.1572 (3)	0.2263 (2)	0.1317 (2)	0.0602 (6)
H12	0.1414	0.1536	0.1761	0.072*
C13	0.0713 (3)	0.2085 (2)	−0.0091 (2)	0.0552 (5)
H13	−0.0036	0.1239	−0.0607	0.066*
C14	0.0936 (3)	0.31287 (18)	−0.0752 (2)	0.0466 (5)
H14	0.0330	0.3008	−0.1719	0.056*
C15	0.2056 (2)	0.43605 (16)	0.00057 (17)	0.0376 (4)
O4	0.1557 (2)	0.53290 (14)	−0.19534 (13)	0.0593 (4)
C16	0.2311 (2)	0.54714 (17)	−0.07165 (17)	0.0405 (4)
C17	0.3535 (2)	0.67684 (17)	0.01047 (18)	0.0393 (4)
C18	0.3757 (3)	0.7879 (2)	−0.0642 (2)	0.0516 (5)
H181	0.4980	0.8401	−0.0144	0.077*
H182	0.2753	0.8541	−0.0699	0.077*
H183	0.3683	0.7421	−0.1570	0.077*

	U11	U22	U33	U12	U13	U23
C1	0.0393 (10)	0.0345 (8)	0.0337 (8)	0.0027 (8)	0.0114 (7)	0.0083 (6)
C2	0.0443 (10)	0.0325 (7)	0.0329 (8)	0.0035 (8)	0.0118 (7)	0.0059 (6)
C3	0.0385 (10)	0.0398 (8)	0.0357 (8)	0.0033 (8)	0.0088 (7)	0.0085 (7)
C4	0.0435 (11)	0.0382 (8)	0.0318 (8)	−0.0001 (8)	0.0065 (7)	0.0066 (6)
N	0.0484 (10)	0.0413 (8)	0.0487 (9)	−0.0045 (8)	0.0063 (7)	−0.0016 (7)
C5	0.0529 (12)	0.0360 (8)	0.0417 (10)	0.0019 (9)	0.0175 (8)	−0.0017 (7)
C6	0.0449 (11)	0.0407 (9)	0.0436 (9)	0.0035 (8)	0.0176 (8)	0.0053 (7)
C7	0.0443 (11)	0.0347 (8)	0.0362 (8)	0.0032 (8)	0.0136 (7)	0.0091 (6)
O1	0.0370 (7)	0.0339 (6)	0.0615 (8)	−0.0006 (5)	0.0156 (6)	−0.0013 (5)
O2	0.0410 (8)	0.0444 (7)	0.0622 (8)	0.0016 (6)	0.0202 (6)	0.0040 (6)
C8	0.0326 (9)	0.0313 (7)	0.0480 (10)	0.0026 (7)	0.0164 (7)	0.0021 (7)
C9	0.0322 (9)	0.0423 (8)	0.0402 (9)	0.0065 (8)	0.0137 (7)	0.0050 (7)
O3	0.0438 (8)	0.0612 (8)	0.0397 (7)	0.0022 (6)	0.0124 (5)	0.0057 (6)
C10	0.0331 (9)	0.0366 (8)	0.0476 (10)	0.0031 (8)	0.0153 (7)	0.0092 (7)
C11	0.0484 (12)	0.0500 (10)	0.0583 (11)	0.0063 (9)	0.0248 (9)	0.0173 (9)
C12	0.0629 (14)	0.0438 (10)	0.0877 (16)	−0.0002 (10)	0.0405 (12)	0.0192 (10)
C13	0.0464 (12)	0.0389 (9)	0.0817 (15)	−0.0021 (9)	0.0316 (10)	−0.0003 (9)
C14	0.0366 (10)	0.0391 (9)	0.0578 (11)	0.0037 (8)	0.0157 (8)	−0.0017 (8)
C15	0.0320 (9)	0.0330 (8)	0.0472 (10)	0.0068 (7)	0.0168 (7)	0.0032 (7)
O4	0.0774 (11)	0.0530 (7)	0.0385 (7)	0.0067 (7)	0.0124 (6)	0.0053 (6)
C16	0.0386 (10)	0.0385 (8)	0.0414 (10)	0.0089 (8)	0.0121 (7)	0.0064 (7)
C17	0.0368 (10)	0.0355 (8)	0.0477 (10)	0.0073 (8)	0.0173 (8)	0.0095 (7)
C18	0.0535 (12)	0.0465 (10)	0.0626 (12)	0.0078 (9)	0.0245 (9)	0.0222 (9)

C1—C2	1.383 (3)	C9—O3	1.213 (2)
C1—C6	1.398 (2)	C9—C10	1.480 (2)
C1—C7	1.463 (2)	C10—C15	1.392 (2)
C2—C3	1.383 (2)	C10—C11	1.397 (2)
C2—H2	0.9500	C11—C12	1.387 (3)
C3—C4	1.407 (2)	C11—H11	0.9500
C3—H3	0.9500	C12—C13	1.382 (3)
C4—N	1.371 (2)	C12—H12	0.9500
C4—C5	1.385 (3)	C13—C14	1.381 (3)
N—H1N	0.89 (2)	C13—H13	0.9500
N—H2N	0.95 (3)	C14—C15	1.394 (2)
C5—C6	1.378 (2)	C14—H14	0.9500
C5—H5	0.9500	C15—C16	1.488 (2)
C6—H6	0.9500	O4—C16	1.215 (2)
C7—O2	1.199 (2)	C16—C17	1.487 (2)
C7—O1	1.388 (2)	C17—C18	1.498 (2)
O1—C8	1.3827 (19)	C18—H181	0.9800
C8—C17	1.333 (2)	C18—H182	0.9800
C8—C9	1.485 (2)	C18—H183	0.9800
C2—C1—C6	118.63 (15)	C15—C10—C11	120.01 (16)
C2—C1—C7	122.37 (15)	C15—C10—C9	120.57 (14)
C6—C1—C7	118.99 (16)	C11—C10—C9	119.42 (16)
C1—C2—C3	121.52 (15)	C12—C11—C10	119.25 (19)
C1—C2—H2	119.2	C12—C11—H11	120.4
C3—C2—H2	119.2	C10—C11—H11	120.4
C2—C3—C4	119.58 (17)	C13—C12—C11	120.62 (17)
C2—C3—H3	120.2	C13—C12—H12	119.7
C4—C3—H3	120.2	C11—C12—H12	119.7
N—C4—C5	121.40 (16)	C14—C13—C12	120.40 (17)
N—C4—C3	119.83 (18)	C14—C13—H13	119.8
C5—C4—C3	118.76 (15)	C12—C13—H13	119.8
C4—N—H1N	116.7 (15)	C13—C14—C15	119.68 (18)
C4—N—H2N	119.0 (13)	C13—C14—H14	120.2
H1N—N—H2N	114 (2)	C15—C14—H14	120.2
C6—C5—C4	121.14 (16)	C10—C15—C14	120.02 (16)
C6—C5—H5	119.4	C10—C15—C16	120.62 (14)
C4—C5—H5	119.4	C14—C15—C16	119.37 (16)
C5—C6—C1	120.36 (17)	O4—C16—C17	120.01 (15)
C5—C6—H6	119.8	O4—C16—C15	121.32 (15)
C1—C6—H6	119.8	C17—C16—C15	118.67 (14)
O2—C7—O1	121.27 (15)	C8—C17—C16	118.88 (14)
O2—C7—C1	128.52 (16)	C8—C17—C18	123.35 (16)
O1—C7—C1	110.20 (15)	C16—C17—C18	117.75 (15)
C8—O1—C7	118.14 (13)	C17—C18—H181	109.5
C17—C8—O1	120.33 (14)	C17—C18—H182	109.5
C17—C8—C9	124.77 (14)	H181—C18—H182	109.5
O1—C8—C9	114.83 (14)	C17—C18—H183	109.5
O3—C9—C10	122.82 (15)	H181—C18—H183	109.5
O3—C9—C8	120.89 (15)	H182—C18—H183	109.5
C10—C9—C8	116.28 (14)
C6—C1—C2—C3	−0.1 (2)	C8—C9—C10—C11	177.37 (17)
C7—C1—C2—C3	178.82 (14)	C15—C10—C11—C12	1.4 (3)
C1—C2—C3—C4	−0.2 (2)	C9—C10—C11—C12	−178.40 (17)
C2—C3—C4—N	−178.97 (15)	C10—C11—C12—C13	−1.5 (3)
C2—C3—C4—C5	0.3 (2)	C11—C12—C13—C14	0.3 (3)
N—C4—C5—C6	179.17 (15)	C12—C13—C14—C15	0.8 (3)
C3—C4—C5—C6	−0.1 (3)	C11—C10—C15—C14	−0.3 (3)
C4—C5—C6—C1	−0.2 (3)	C9—C10—C15—C14	179.56 (16)
C2—C1—C6—C5	0.3 (2)	C11—C10—C15—C16	179.70 (16)
C7—C1—C6—C5	−178.65 (15)	C9—C10—C15—C16	−0.5 (3)
C2—C1—C7—O2	−171.14 (16)	C13—C14—C15—C10	−0.9 (3)
C6—C1—C7—O2	7.8 (3)	C13—C14—C15—C16	179.15 (17)
C2—C1—C7—O1	7.5 (2)	C10—C15—C16—O4	−179.69 (17)
C6—C1—C7—O1	−173.56 (14)	C14—C15—C16—O4	0.3 (3)
O2—C7—O1—C8	4.8 (2)	C10—C15—C16—C17	1.0 (3)
C1—C7—O1—C8	−174.01 (13)	C14—C15—C16—C17	−179.01 (16)
C7—O1—C8—C17	89.9 (2)	O1—C8—C17—C16	171.84 (14)
C7—O1—C8—C9	−92.86 (17)	C9—C8—C17—C16	−5.1 (3)
C17—C8—C9—O3	−175.24 (17)	O1—C8—C17—C18	−7.0 (3)
O1—C8—C9—O3	7.7 (2)	C9—C8—C17—C18	176.11 (16)
C17—C8—C9—C10	5.5 (3)	O4—C16—C17—C8	−177.60 (17)
O1—C8—C9—C10	−171.56 (14)	C15—C16—C17—C8	1.7 (2)
O3—C9—C10—C15	178.30 (17)	O4—C16—C17—C18	1.3 (3)
C8—C9—C10—C15	−2.5 (2)	C15—C16—C17—C18	−179.42 (16)
O3—C9—C10—C11	−1.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N—H2N···O3i	0.95 (3)	2.13 (3)	2.960 (2)	145.6 (19)
N—H1N···O4ii	0.89 (2)	2.25 (2)	3.045 (2)	147.3 (19)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—H2N⋯O3i	0.95 (3)	2.13 (3)	2.960 (2)	145.6 (19)
N—H1N⋯O4ii	0.89 (2)	2.25 (2)	3.045 (2)	147.3 (19)

Symmetry codes: (i) ; (ii) .