1,3-Dihydr-oxy-9,10-dioxo-9,10-di-hydro-anthracene-2-carbaldehyde.

The title compound, C(15)H(8)O(5), also known as nordamnacanthal, was isolated from the Malaysian Morinda citrifolia L. The 20 non-H atoms are coplanar. The structure is stabilized by intra-molecular O-H⋯O hydrogen bonds and inter-molecular O-H⋯O and C-H⋯O hydrogen bonds, forming bilayers of mol-ecular tapes with alternating stacking directions along the a axis.

Related literature

For related literature, see: Chan-Blanco et al. (2006 ▶); Ismail (1998 ▶); Ohsawa & Ohba (1993 ▶); Singh et al. (1984 ▶); Whistler (1985 ▶); Wijnsma & Verpoorte (1986 ▶); Zhu et al. (2008 ▶).

Experimental

Crystal data

C15H8O5

M = 268.21

Monoclinic,

a = 10.547 (2) Å

b = 5.669 (1) Å

c = 20.231 (3) Å

β = 110.62 (4)°

V = 1132.1 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 293 (2) K

0.60 × 0.39 × 0.14 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: none

14030 measured reflections

2298 independent reflections

1554 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.150

S = 1.06

2296 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.20 e Å−3

Data collection: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT (Nonius, 1999 ▶); cell refinement: DENZO and COLLECT; data reduction: SCALEPACK (Otwinowski & Minor, 1997 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808004169/bg2162sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808004169/bg2162Isup2.hkl

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

C15H8O5	F000 = 552
Mr = 268.21	Dx = 1.574 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71070 Å
Hall symbol: -P 2ybc	Cell parameters from 10451 reflections
a = 10.547 (2) Å	θ = 0.4–26.4º
b = 5.669 (1) Å	µ = 0.12 mm−1
c = 20.231 (3) Å	T = 293 (2) K
β = 110.62 (4)º	Prism, orange
V = 1132.1 (5) Å3	0.60 × 0.39 × 0.14 mm
Z = 4

Nonius KappaCCD diffractometer	1554 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.029
Monochromator: graphite	θmax = 26.4º
T = 293(2) K	θmin = 2.1º
φ and ω scans	h = 0→13
Absorption correction: none	k = −7→0
14030 measured reflections	l = −25→22
2298 independent 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)] = 0.051	H-atom parameters constrained
wR(F2) = 0.150	w = 1/[σ2(Fo2) + (0.0705P)2 + 0.3487P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2296 reflections	Δρmax = 0.27 e Å−3
181 parameters	Δρmin = −0.20 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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 (2298) except two reflections with Delta(F2)/e.s.d. greater than 9 (2296). 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
O4	0.32777 (16)	1.4401 (3)	−0.05914 (8)	0.0669 (5)
O5	0.02849 (14)	0.7077 (2)	−0.03142 (7)	0.0531 (4)
O1	0.22406 (15)	0.5649 (2)	0.07880 (7)	0.0525 (4)
H1	0.1487	0.5610	0.0479	0.063*
O3	0.62014 (15)	1.0321 (3)	0.15870 (9)	0.0746 (5)
H3	0.6408	0.9283	0.1889	0.090*
O2	0.58762 (18)	0.6610 (3)	0.22568 (9)	0.0811 (6)
C6	0.2604 (2)	1.2727 (3)	−0.05264 (10)	0.0437 (5)
C7	0.12238 (19)	1.2323 (3)	−0.10446 (9)	0.0388 (5)
C12	0.04523 (18)	1.0390 (3)	−0.09796 (9)	0.0364 (4)
C13	0.09986 (19)	0.8728 (3)	−0.03790 (10)	0.0388 (5)
C14	0.23549 (18)	0.9106 (3)	0.01290 (10)	0.0377 (4)
C5	0.31419 (18)	1.1053 (3)	0.00715 (10)	0.0396 (5)
C4	0.4429 (2)	1.1451 (4)	0.05601 (11)	0.0493 (5)
H4	0.4935	1.2742	0.0513	0.059*
C3	0.4949 (2)	0.9898 (4)	0.11180 (11)	0.0521 (6)
C2	0.4211 (2)	0.7925 (4)	0.11979 (10)	0.0461 (5)
C1	0.2905 (2)	0.7533 (3)	0.06963 (10)	0.0425 (5)
C15	0.4762 (3)	0.6333 (4)	0.17886 (13)	0.0652 (7)
H15	0.4247	0.5031	0.1817	0.078*
C11	−0.0846 (2)	1.0056 (4)	−0.14710 (10)	0.0446 (5)
H11	−0.1359	0.8766	−0.1430	0.054*
C10	−0.1371 (2)	1.1638 (4)	−0.20178 (10)	0.0509 (5)
H10	−0.2239	1.1414	−0.2346	0.061*
C9	−0.0613 (2)	1.3547 (4)	−0.20791 (11)	0.0539 (6)
H9	−0.0975	1.4613	−0.2447	0.065*
C8	0.0679 (2)	1.3894 (4)	−0.15996 (10)	0.0486 (5)
H8	0.1185	1.5183	−0.1648	0.058*

	U11	U22	U33	U12	U13	U23
O4	0.0621 (10)	0.0626 (10)	0.0708 (11)	−0.0288 (8)	0.0169 (8)	0.0066 (8)
O5	0.0512 (9)	0.0466 (8)	0.0591 (9)	−0.0150 (7)	0.0163 (7)	0.0068 (7)
O1	0.0511 (9)	0.0471 (8)	0.0565 (9)	−0.0020 (7)	0.0155 (7)	0.0087 (7)
O3	0.0437 (9)	0.0866 (12)	0.0726 (11)	−0.0075 (8)	−0.0056 (8)	−0.0060 (9)
O2	0.0657 (11)	0.0934 (13)	0.0606 (11)	0.0183 (10)	−0.0071 (9)	0.0054 (9)
C6	0.0458 (11)	0.0411 (11)	0.0474 (11)	−0.0107 (9)	0.0201 (9)	−0.0052 (9)
C7	0.0434 (11)	0.0367 (10)	0.0381 (10)	−0.0049 (8)	0.0167 (9)	−0.0044 (8)
C12	0.0367 (10)	0.0360 (10)	0.0374 (10)	−0.0028 (8)	0.0142 (8)	−0.0048 (8)
C13	0.0419 (11)	0.0355 (10)	0.0421 (11)	−0.0054 (8)	0.0187 (9)	−0.0036 (8)
C14	0.0370 (10)	0.0388 (10)	0.0378 (10)	0.0018 (8)	0.0138 (8)	−0.0027 (8)
C5	0.0359 (10)	0.0413 (10)	0.0426 (11)	−0.0048 (8)	0.0152 (8)	−0.0075 (8)
C4	0.0450 (12)	0.0496 (12)	0.0536 (13)	−0.0085 (9)	0.0176 (10)	−0.0075 (10)
C3	0.0386 (11)	0.0605 (13)	0.0511 (13)	0.0012 (10)	0.0081 (10)	−0.0113 (11)
C2	0.0427 (11)	0.0504 (12)	0.0423 (11)	0.0075 (9)	0.0112 (9)	−0.0026 (9)
C1	0.0432 (11)	0.0404 (11)	0.0474 (11)	0.0016 (8)	0.0202 (9)	−0.0033 (8)
C15	0.0664 (15)	0.0655 (15)	0.0561 (14)	0.0136 (12)	0.0122 (12)	0.0028 (12)
C11	0.0413 (11)	0.0467 (11)	0.0457 (11)	−0.0068 (9)	0.0149 (9)	−0.0065 (9)
C10	0.0433 (11)	0.0603 (13)	0.0430 (11)	0.0026 (10)	0.0075 (9)	−0.0059 (10)
C9	0.0634 (14)	0.0528 (13)	0.0422 (12)	0.0073 (11)	0.0146 (11)	0.0072 (9)
C8	0.0578 (13)	0.0430 (11)	0.0471 (12)	−0.0066 (9)	0.0209 (11)	0.0014 (9)

O4—C6	1.220 (2)	C14—C5	1.410 (3)
O5—C13	1.237 (2)	C5—C4	1.388 (3)
O1—C1	1.326 (2)	C4—C3	1.383 (3)
O1—H1	0.8200	C4—H4	0.9300
O3—C3	1.349 (3)	C3—C2	1.404 (3)
O3—H3	0.8200	C2—C1	1.411 (3)
O2—C15	1.233 (3)	C2—C15	1.446 (3)
C6—C7	1.482 (3)	C15—H15	0.9300
C6—C5	1.484 (3)	C11—C10	1.380 (3)
C7—C8	1.389 (3)	C11—H11	0.9300
C7—C12	1.399 (2)	C10—C9	1.377 (3)
C12—C11	1.393 (3)	C10—H10	0.9300
C12—C13	1.484 (3)	C9—C8	1.380 (3)
C13—C14	1.454 (3)	C9—H9	0.9300
C14—C1	1.407 (3)	C8—H8	0.9300
C1—O1—H1	109.5	O3—C3—C2	120.4 (2)
C3—O3—H3	109.5	C4—C3—C2	121.61 (18)
O4—C6—C7	120.56 (18)	C3—C2—C1	118.88 (18)
O4—C6—C5	121.01 (18)	C3—C2—C15	121.0 (2)
C7—C6—C5	118.43 (16)	C1—C2—C15	120.1 (2)
C8—C7—C12	119.32 (18)	O1—C1—C14	122.54 (18)
C8—C7—C6	119.77 (17)	O1—C1—C2	117.17 (18)
C12—C7—C6	120.91 (17)	C14—C1—C2	120.29 (18)
C11—C12—C7	119.84 (17)	O2—C15—C2	123.5 (3)
C11—C12—C13	119.92 (16)	O2—C15—H15	118.2
C7—C12—C13	120.23 (16)	C2—C15—H15	118.2
O5—C13—C14	121.38 (17)	C10—C11—C12	120.01 (19)
O5—C13—C12	119.46 (17)	C10—C11—H11	120.0
C14—C13—C12	119.15 (16)	C12—C11—H11	120.0
C1—C14—C5	118.53 (17)	C9—C10—C11	120.08 (19)
C1—C14—C13	120.26 (17)	C9—C10—H10	120.0
C5—C14—C13	121.21 (17)	C11—C10—H10	120.0
C4—C5—C14	121.66 (18)	C10—C9—C8	120.6 (2)
C4—C5—C6	118.30 (17)	C10—C9—H9	119.7
C14—C5—C6	120.04 (17)	C8—C9—H9	119.7
C3—C4—C5	119.03 (19)	C9—C8—C7	120.12 (19)
C3—C4—H4	120.5	C9—C8—H8	119.9
C5—C4—H4	120.5	C7—C8—H8	119.9
O3—C3—C4	118.0 (2)
O4—C6—C7—C8	−1.6 (3)	C6—C5—C4—C3	−179.58 (18)
C5—C6—C7—C8	178.31 (17)	C5—C4—C3—O3	−179.91 (17)
O4—C6—C7—C12	179.08 (18)	C5—C4—C3—C2	0.5 (3)
C5—C6—C7—C12	−1.0 (3)	O3—C3—C2—C1	−179.82 (18)
C8—C7—C12—C11	0.3 (3)	C4—C3—C2—C1	−0.3 (3)
C6—C7—C12—C11	179.58 (17)	O3—C3—C2—C15	1.2 (3)
C8—C7—C12—C13	−178.19 (17)	C4—C3—C2—C15	−179.25 (19)
C6—C7—C12—C13	1.1 (3)	C5—C14—C1—O1	−179.51 (17)
C11—C12—C13—O5	−1.1 (3)	C13—C14—C1—O1	1.1 (3)
C7—C12—C13—O5	177.34 (17)	C5—C14—C1—C2	0.7 (3)
C11—C12—C13—C14	−179.93 (16)	C13—C14—C1—C2	−178.70 (17)
C7—C12—C13—C14	−1.5 (3)	C3—C2—C1—O1	179.83 (17)
O5—C13—C14—C1	2.3 (3)	C15—C2—C1—O1	−1.2 (3)
C12—C13—C14—C1	−178.89 (16)	C3—C2—C1—C14	−0.3 (3)
O5—C13—C14—C5	−177.04 (18)	C15—C2—C1—C14	178.65 (18)
C12—C13—C14—C5	1.8 (3)	C3—C2—C15—O2	1.2 (4)
C1—C14—C5—C4	−0.4 (3)	C1—C2—C15—O2	−177.7 (2)
C13—C14—C5—C4	178.95 (17)	C7—C12—C11—C10	−0.4 (3)
C1—C14—C5—C6	178.98 (16)	C13—C12—C11—C10	178.07 (17)
C13—C14—C5—C6	−1.7 (3)	C12—C11—C10—C9	0.0 (3)
O4—C6—C5—C4	0.6 (3)	C11—C10—C9—C8	0.4 (3)
C7—C6—C5—C4	−179.34 (17)	C10—C9—C8—C7	−0.5 (3)
O4—C6—C5—C14	−178.84 (19)	C12—C7—C8—C9	0.2 (3)
C7—C6—C5—C14	1.3 (3)	C6—C7—C8—C9	−179.14 (18)
C14—C5—C4—C3	−0.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.82	1.86	2.590 (3)	148
O1—H1···O5	0.82	1.86	2.577 (2)	146
O1—H1···O5i	0.82	2.34	2.933 (2)	130
C4—H4···O4ii	0.93	2.45	3.358 (2)	166
C10—H10···O2iii	0.93	2.53	3.312 (3)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2	0.82	1.86	2.590 (3)	148
O1—H1⋯O5	0.82	1.86	2.577 (2)	146
O1—H1⋯O5i	0.82	2.34	2.933 (2)	130
C4—H4⋯O4ii	0.93	2.45	3.358 (2)	166
C10—H10⋯O2iii	0.93	2.53	3.312 (3)	142

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