2-Formyl-3-hydr-oxy-9,10-anthroquinone.

The mol-ecule of the title compound, C(15)H(8)O(4), is approximately planar. An intra-molecular O-H⋯O hydrogen bond is observed between the hydr-oxy and formyl groups. The crystal used was a nonmerohedral twin, with a minor twin component of 15.9%.

Related literature

For anti­leshmanial and anti­plasmodial activities, see: Sittie et al. (1999 ▶). For the treatment of twinned diffraction data, see: Spek (2003 ▶).

Experimental

Crystal data

C15H8O4

M = 252.21

Triclinic,

a = 6.9194 (2) Å

b = 8.0650 (2) Å

c = 10.7601 (3) Å

α = 86.250 (2)°

β = 83.214 (2)°

γ = 64.692 (2)°

V = 538.96 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 100 (2) K

0.22 × 0.04 × 0.04 mm

Data collection

Bruker SMART APEXII area-detector diffractometer

Absorption correction: none

4946 measured reflections

2419 independent reflections

1880 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.087

wR(F 2) = 0.343

S = 1.11

2419 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.44 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2008 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808032224/ci2681sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808032224/ci2681Isup2.hkl

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

C15H8O4	Z = 2
Mr = 252.21	F(000) = 260
Triclinic, P1	Dx = 1.554 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9194 (2) Å	Cell parameters from 1888 reflections
b = 8.0650 (2) Å	θ = 3.3–28.3°
c = 10.7601 (3) Å	µ = 0.11 mm−1
α = 86.250 (2)°	T = 100 K
β = 83.214 (2)°	Block, yellow
γ = 64.692 (2)°	0.22 × 0.04 × 0.04 mm
V = 538.96 (3) Å3

Bruker SMART APEXII area-detector diffractometer	1880 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
graphite	θmax = 27.5°, θmin = 2.8°
ω scans	h = −8→8
4946 measured reflections	k = −10→10
2419 independent reflections	l = −13→13

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.087	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.343	H-atom parameters constrained
S = 1.11	w = 1/[σ2(Fo2) + (0.1778P)2 + 2.2381P] where P = (Fo2 + 2Fc2)/3
2419 reflections	(Δ/σ)max = 0.001
173 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.44 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.3155 (6)	0.6486 (5)	0.0888 (3)	0.0251 (8)
O2	0.2501 (6)	0.3493 (5)	0.0941 (3)	0.0242 (8)
H2	0.2611	0.4345	0.0490	0.029*
O3	0.2366 (5)	−0.0898 (4)	0.4383 (3)	0.0153 (7)
O4	0.2779 (5)	0.4648 (4)	0.6688 (3)	0.0172 (7)
C1	0.3060 (7)	0.6395 (6)	0.2041 (4)	0.0178 (9)
H1	0.3171	0.7336	0.2474	0.021*
C2	0.2786 (7)	0.4901 (6)	0.2772 (4)	0.0143 (9)
C3	0.2544 (7)	0.3500 (6)	0.2187 (4)	0.0161 (9)
C4	0.2356 (7)	0.2059 (6)	0.2894 (4)	0.0152 (9)
H4	0.2187	0.1116	0.2500	0.018*
C5	0.2419 (6)	0.2016 (5)	0.4183 (4)	0.0123 (8)
C6	0.2335 (6)	0.0406 (5)	0.4916 (4)	0.0112 (8)
C7	0.2285 (6)	0.0417 (5)	0.6299 (4)	0.0112 (8)
C8	0.2117 (7)	−0.1043 (6)	0.7003 (4)	0.0139 (8)
H8	0.1986	−0.1999	0.6601	0.017*
C9	0.2144 (7)	−0.1091 (6)	0.8286 (4)	0.0179 (9)
H9	0.2031	−0.2083	0.8766	0.021*
C10	0.2336 (7)	0.0310 (6)	0.8883 (4)	0.0188 (9)
H10	0.2353	0.0269	0.9767	0.023*
C11	0.2503 (7)	0.1762 (6)	0.8187 (4)	0.0173 (9)
H11	0.2645	0.2709	0.8594	0.021*
C12	0.2462 (6)	0.1835 (5)	0.6895 (4)	0.0113 (8)
C13	0.2641 (6)	0.3403 (6)	0.6165 (4)	0.0126 (8)
C14	0.2621 (6)	0.3426 (5)	0.4787 (4)	0.0120 (8)
C15	0.2815 (7)	0.4851 (6)	0.4072 (4)	0.0133 (8)
H15	0.2968	0.5801	0.4468	0.016*

	U11	U22	U33	U12	U13	U23
O1	0.038 (2)	0.0258 (18)	0.0125 (16)	−0.0155 (16)	−0.0033 (13)	0.0054 (13)
O2	0.046 (2)	0.0283 (18)	0.0063 (15)	−0.0226 (17)	−0.0062 (13)	0.0020 (12)
O3	0.0194 (15)	0.0131 (14)	0.0147 (15)	−0.0079 (12)	−0.0028 (11)	−0.0009 (11)
O4	0.0228 (16)	0.0148 (15)	0.0165 (15)	−0.0103 (13)	−0.0003 (12)	−0.0039 (11)
C1	0.021 (2)	0.017 (2)	0.016 (2)	−0.0078 (17)	−0.0040 (16)	0.0035 (16)
C2	0.0146 (19)	0.0149 (19)	0.0119 (19)	−0.0053 (16)	−0.0011 (14)	0.0030 (15)
C3	0.017 (2)	0.021 (2)	0.0103 (19)	−0.0080 (17)	−0.0030 (15)	0.0010 (15)
C4	0.016 (2)	0.016 (2)	0.014 (2)	−0.0074 (16)	−0.0007 (15)	−0.0025 (15)
C5	0.0106 (18)	0.0107 (18)	0.0135 (19)	−0.0032 (14)	0.0010 (14)	0.0003 (14)
C6	0.0099 (17)	0.0105 (18)	0.0121 (19)	−0.0036 (14)	−0.0001 (14)	−0.0004 (14)
C7	0.0109 (18)	0.0114 (18)	0.0103 (18)	−0.0038 (14)	−0.0025 (13)	0.0011 (14)
C8	0.0145 (19)	0.0118 (18)	0.015 (2)	−0.0053 (15)	−0.0023 (15)	0.0013 (14)
C9	0.019 (2)	0.017 (2)	0.017 (2)	−0.0081 (17)	−0.0012 (16)	0.0055 (16)
C10	0.024 (2)	0.022 (2)	0.0110 (19)	−0.0100 (18)	−0.0009 (16)	0.0026 (16)
C11	0.021 (2)	0.018 (2)	0.013 (2)	−0.0084 (17)	−0.0008 (16)	−0.0009 (15)
C12	0.0108 (18)	0.0112 (18)	0.0109 (18)	−0.0039 (14)	−0.0002 (14)	−0.0005 (14)
C13	0.0112 (18)	0.0125 (19)	0.0139 (19)	−0.0046 (15)	−0.0015 (14)	−0.0010 (14)
C14	0.0116 (18)	0.0112 (18)	0.0127 (19)	−0.0044 (14)	0.0001 (14)	−0.0002 (14)
C15	0.0138 (19)	0.0112 (18)	0.014 (2)	−0.0049 (15)	0.0006 (14)	−0.0017 (14)

O1—C1	1.234 (5)	C7—C8	1.398 (5)
O2—C3	1.345 (5)	C7—C12	1.403 (5)
O2—H2	0.84	C8—C9	1.380 (6)
O3—C6	1.222 (5)	C8—H8	0.95
O4—C13	1.226 (5)	C9—C10	1.397 (6)
C1—C2	1.464 (6)	C9—H9	0.95
C1—H1	0.95	C10—C11	1.388 (6)
C2—C15	1.400 (6)	C10—H10	0.95
C2—C3	1.407 (6)	C11—C12	1.391 (6)
C3—C4	1.391 (6)	C11—H11	0.95
C4—C5	1.390 (6)	C12—C13	1.487 (5)
C4—H4	0.95	C13—C14	1.483 (6)
C5—C14	1.410 (6)	C14—C15	1.387 (6)
C5—C6	1.494 (5)	C15—H15	0.95
C6—C7	1.485 (5)
C3—O2—H2	120.0	C9—C8—H8	120.1
O1—C1—C2	122.8 (4)	C7—C8—H8	120.1
O1—C1—H1	118.6	C8—C9—C10	120.4 (4)
C2—C1—H1	118.6	C8—C9—H9	119.8
C15—C2—C3	119.7 (4)	C10—C9—H9	119.8
C15—C2—C1	119.1 (4)	C11—C10—C9	120.0 (4)
C3—C2—C1	121.2 (4)	C11—C10—H10	120.0
O2—C3—C4	117.9 (4)	C9—C10—H10	120.0
O2—C3—C2	121.8 (4)	C10—C11—C12	120.2 (4)
C4—C3—C2	120.3 (4)	C10—C11—H11	119.9
C5—C4—C3	119.2 (4)	C12—C11—H11	119.9
C5—C4—H4	120.4	C11—C12—C7	119.6 (4)
C3—C4—H4	120.4	C11—C12—C13	119.4 (4)
C4—C5—C14	121.2 (4)	C7—C12—C13	121.1 (3)
C4—C5—C6	118.4 (4)	O4—C13—C14	121.0 (4)
C14—C5—C6	120.3 (4)	O4—C13—C12	121.0 (4)
O3—C6—C7	121.3 (4)	C14—C13—C12	118.0 (3)
O3—C6—C5	120.5 (4)	C15—C14—C5	119.0 (4)
C7—C6—C5	118.1 (3)	C15—C14—C13	119.7 (4)
C8—C7—C12	120.1 (4)	C5—C14—C13	121.3 (4)
C8—C7—C6	118.9 (4)	C14—C15—C2	120.5 (4)
C12—C7—C6	121.0 (3)	C14—C15—H15	119.8
C9—C8—C7	119.7 (4)	C2—C15—H15	119.8
O1—C1—C2—C15	176.5 (4)	C10—C11—C12—C7	−1.0 (6)
O1—C1—C2—C3	−2.1 (7)	C10—C11—C12—C13	180.0 (4)
C15—C2—C3—O2	179.8 (4)	C8—C7—C12—C11	1.0 (6)
C1—C2—C3—O2	−1.7 (7)	C6—C7—C12—C11	−177.2 (4)
C15—C2—C3—C4	−0.7 (7)	C8—C7—C12—C13	−180.0 (3)
C1—C2—C3—C4	177.9 (4)	C6—C7—C12—C13	1.8 (6)
O2—C3—C4—C5	179.3 (4)	C11—C12—C13—O4	−1.5 (6)
C2—C3—C4—C5	−0.3 (7)	C7—C12—C13—O4	179.4 (4)
C3—C4—C5—C14	1.4 (6)	C11—C12—C13—C14	179.2 (4)
C3—C4—C5—C6	−176.7 (4)	C7—C12—C13—C14	0.2 (6)
C4—C5—C6—O3	5.1 (6)	C4—C5—C14—C15	−1.6 (6)
C14—C5—C6—O3	−173.0 (4)	C6—C5—C14—C15	176.4 (3)
C4—C5—C6—C7	−176.8 (4)	C4—C5—C14—C13	178.7 (4)
C14—C5—C6—C7	5.1 (6)	C6—C5—C14—C13	−3.2 (6)
O3—C6—C7—C8	−4.6 (6)	O4—C13—C14—C15	1.6 (6)
C5—C6—C7—C8	177.4 (4)	C12—C13—C14—C15	−179.1 (4)
O3—C6—C7—C12	173.7 (4)	O4—C13—C14—C5	−178.7 (4)
C5—C6—C7—C12	−4.4 (6)	C12—C13—C14—C5	0.6 (6)
C12—C7—C8—C9	−0.5 (6)	C5—C14—C15—C2	0.7 (6)
C6—C7—C8—C9	177.7 (4)	C13—C14—C15—C2	−179.6 (4)
C7—C8—C9—C10	0.0 (7)	C3—C2—C15—C14	0.4 (6)
C8—C9—C10—C11	0.0 (7)	C1—C2—C15—C14	−178.1 (4)
C9—C10—C11—C12	0.5 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.84	2.00	2.635 (5)	132

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1	0.84	2.00	2.635 (5)	132