6-[3-(2,4-Dimethyl­anilino)-2-hydroxy­prop­oxy]-1,8-dihydr­oxy-3-methyl-9,10-dihydro­anthracene-9,10-dione

Wang, X.-P.; Xu, W.

doi:10.1107/S1600536809002347

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o367

doi:10.1107/S1600536809002347

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6-[3-(2,4-Dimethylanilino)-2-hydroxypropoxy]-1,8-dihydroxy-3-methyl-9,10-dihydroanthracene-9,10-dione

Xing-Po Wang ^a ^* and Wenfang Xu ^b

^aSchool of Chemistry and Chemical Engineering, Shandong University, Shandong 250100, People's Republic of China, and ^bSchool of Pharmacy, Shandong University, Shandong 250012, People's Republic of China
^*Correspondence e-mail: xpw6@163.com

(Received 26 December 2008; accepted 18 January 2009; online 23 January 2009)

In the title compound, C₂₆H₂₅NO₆, the anthraquinone ring system forms a dihedral angle of 15.5 (1)° with the benzene ring of the dimethylaniline group. Intramolecular O—H⋯O hydrogen bonding is observed between the carbonyl and two hydroxyl groups. The molecules are linked into a ribbon-like structure along the [100] direction by O—H⋯N and C—H⋯O hydrogen bonds. The crystal used was twinned via a 180° rotation about [100]. The ratio of the two twin components is 0.947 (1):0.053 (1).

Related literature

For the biological properties of emodin and its derivatives, see: Srinivas et al. (2003 ); Teich et al., 2004 ; Wang & Xu (2005 ). For a related structure, see: Wang et al. (2006 ).

Experimental

Crystal data

C₂₆H₂₅NO₆
M_r = 447.47
Monoclinic, P 2₁ /c
a = 5.0668 (3) Å
b = 29.7496 (17) Å
c = 14.2201 (8) Å
β = 90.530 (4)°
V = 2143.4 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 295 (2) K
0.32 × 0.14 × 0.04 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker,2005 ) T_min = 0.969, T_max = 0.996
17905 measured reflections
4939 independent reflections
2028 reflections with I > 2σ(I)
R_int = 0.072

Refinement

R[F² > 2σ(F²)] = 0.072
wR(F²) = 0.232
S = 0.99
4939 reflections
305 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.65 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1D⋯O2	0.82	1.86	2.575 (4)	145
O3—H3A⋯O2	0.82	1.83	2.556 (4)	147
O6—H6⋯N1ⁱ	0.82	2.40	3.218 (5)	177
C15—H15⋯O4ⁱⁱ	0.93	2.43	3.334 (4)	164
Symmetry codes: (i) x-1, y, z; (ii) -x, -y+2, -z+1.

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

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809002347/ci2754sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809002347/ci2754Isup2.hkl

checkCIF report

Comment top

Emodin and its derivatives have been found to possess diverse biological properties, such as antimicrobial, antiviral, antitumor, anti-inflammatory, anti-oxidant, immunosuppressive, anti-ulcerogenic, fungicidal and chemopreventive activities (Wang & Xu, 2005; Teich et al., 2004; Srinivas et al., 2003). As part of our ongoing research on emodin derivatives (Wang & Xu, 2005; Wang et al., 2006), we report here the crystal structure of the title compound.

The molecular structure of the title compound is illustrated in Fig. 1. The anthraquinone ring system is essentially planar and it forms a dihedral angle of 15.5 (1)° with the benzene ring of the dimethylaniline group. There are two intramolecular O—H···O hydrogen-bonding interactions between the carbonyl and two hydroxy groups (Fig. 1).

The molecules are linked into a ribbon-like structure along the [100] by intermolecular O—H···N and C—H···O hydrogen bonds (Table 1 and Fig.2).

Related literature top

For the biological properties of emodin and its derivatives, see: Srinivas et al. (2003); Teich et al., 2004; Wang & Xu (2005). For a related structure, see: Wang et al. (2006).

Experimental top

A mixture of emodin (10 mmol) and epichlorohydrin (421 mmol, 33 ml) was stirred under reflux in a solution of potassium hydroxide (10 mmol) in water (3 ml) until the disappearance of the starting material, as evidenced by thin-layer chromatography (about 4 h). After the reaction was over, the solvent was removed in vacuo and the residue was partitioned between chloroform (50 ml) and distilled water (20 ml). The organic phase was washed with water (15 ml) and brine (15 ml), and dried over anhydrous sodium sulfate. The solvent was removed to give the key intermediate, 1,8-Dihydroxy-3-methyl-6-(oxiran-2-ylmethoxy)-9,10-dihydroanthracene-9,10-dione (Wang et al., 2006) as a yellow oil, which was purified by flash chromatography (silica gel, petroleum ether–acetone 3:1). To a solution of above intermediate (0.326 g, 1 mmol) in chloroform was added 2,4-dimethylaniline (1.1 mmol). The mixture was refluxed with stirring and monitored by TLC until the reaction was completed. The crude product was purified by column chromatography (petroleum ether–acetone 3:1) to afford the title compound, which was dissolved in methanol (15 ml) and kept at room temperature for 15 d to get yellow single crystals.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. Dashed lines indicate hydrogen-bonding interactions.
	Fig. 2. The molecular packing of the title compound, viewed along the a axis. Dashed lines indicate hydrogen-bonding interactions.

6-[3-(2,4-Dimethylanilino)-2-hydroxypropoxy]-1,8-dihydroxy-3-methyl-9,10- dihydroanthracene-9,10-dione top

Crystal data top

C₂₆H₂₅NO₆	F(000) = 944
M_r = 447.47	D_x = 1.387 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 469–470 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 5.0668 (3) Å	Cell parameters from 1559 reflections
b = 29.7496 (17) Å	θ = 2.5–19.5°
c = 14.2201 (8) Å	µ = 0.10 mm⁻¹
β = 90.530 (4)°	T = 295 K
V = 2143.4 (2) Å³	Plate, yellow
Z = 4	0.32 × 0.14 × 0.04 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	4939 independent reflections
Radiation source: fine-focus sealed tube	2028 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.072
ϕ and ω scans	θ_max = 27.6°, θ_min = 0.7°
Absorption correction: multi-scan (SADABS; Bruker,2005)	h = −5→6
T_min = 0.969, T_max = 0.996	k = −38→30
17905 measured reflections	l = −13→18

Refinement top

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)] = 0.072	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.232	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.11P)²] where P = (F_o² + 2F_c²)/3
4939 reflections	(Δ/σ)_max = 0.001
305 parameters	Δρ_max = 0.65 e Å⁻³
1 restraint	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₂₆H₂₅NO₆	V = 2143.4 (2) Å³
M_r = 447.47	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.0668 (3) Å	µ = 0.10 mm⁻¹
b = 29.7496 (17) Å	T = 295 K
c = 14.2201 (8) Å	0.32 × 0.14 × 0.04 mm
β = 90.530 (4)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4939 independent reflections
Absorption correction: multi-scan (SADABS; Bruker,2005)	2028 reflections with I > 2σ(I)
T_min = 0.969, T_max = 0.996	R_int = 0.072
17905 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.072	1 restraint
wR(F²) = 0.232	H-atom parameters constrained
S = 0.99	Δρ_max = 0.65 e Å⁻³
4939 reflections	Δρ_min = −0.28 e Å⁻³
305 parameters

Special details top

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. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	−1.0367 (9)	1.13766 (15)	0.5591 (3)	0.0676 (13)
H2D	−1.1427	1.1638	0.5469	0.101*
H1B	−0.9129	1.1440	0.6088	0.101*
H1C	−1.1484	1.1132	0.5774	0.101*
C2	−0.8902 (8)	1.12513 (13)	0.4719 (3)	0.0524 (10)
C3	−0.9564 (8)	1.14342 (13)	0.3858 (3)	0.0600 (11)
H3	−1.0914	1.1645	0.3824	0.072*
C4	−0.8269 (8)	1.13118 (13)	0.3037 (3)	0.0535 (11)
C5	−0.6234 (7)	1.09890 (12)	0.3064 (2)	0.0454 (9)
C6	−0.5564 (7)	1.08053 (12)	0.3954 (2)	0.0431 (9)
C7	−0.6889 (7)	1.09336 (13)	0.4748 (3)	0.0507 (10)
H7	−0.6426	1.0804	0.5322	0.061*
C8	−0.4926 (7)	1.08413 (12)	0.2218 (3)	0.0453 (10)
C9	−0.2884 (7)	1.05060 (12)	0.2275 (2)	0.0431 (9)
C10	−0.2116 (7)	1.03164 (12)	0.3150 (2)	0.0409 (9)
C11	−0.3414 (7)	1.04653 (13)	0.4030 (3)	0.0461 (10)
C12	−0.1578 (8)	1.03526 (13)	0.1470 (2)	0.0497 (10)
C13	0.0369 (8)	1.00294 (13)	0.1525 (3)	0.0516 (10)
H13	0.1215	0.9933	0.0983	0.062*
C14	0.1057 (7)	0.98486 (12)	0.2389 (3)	0.0457 (9)
C15	−0.0191 (7)	0.99984 (12)	0.3210 (2)	0.0448 (9)
H15	0.0298	0.9881	0.3792	0.054*
C16	0.4139 (8)	0.93266 (13)	0.1716 (3)	0.0549 (11)
H16A	0.5121	0.9552	0.1370	0.066*
H16B	0.2815	0.9198	0.1300	0.066*
C17	0.5967 (8)	0.89666 (13)	0.2081 (3)	0.0526 (10)
H17	0.7291	0.9111	0.2487	0.063*
C18	0.7400 (8)	0.87514 (14)	0.1259 (3)	0.0536 (11)
H18A	0.6129	0.8624	0.0820	0.064*
H18B	0.8421	0.8977	0.0930	0.064*
C19	1.0724 (7)	0.81541 (12)	0.1014 (3)	0.0465 (10)
C20	1.1235 (8)	0.82906 (14)	0.0102 (3)	0.0530 (10)
H20	1.0373	0.8541	−0.0145	0.064*
C21	1.3044 (8)	0.80537 (15)	−0.0453 (3)	0.0572 (11)
H21	1.3358	0.8149	−0.1064	0.069*
C22	1.4366 (8)	0.76818 (15)	−0.0109 (3)	0.0561 (11)
C23	1.6400 (9)	0.74387 (17)	−0.0682 (3)	0.0833 (15)
H23A	1.7896	0.7367	−0.0290	0.125*
H23B	1.6951	0.7627	−0.1192	0.125*
H23C	1.5650	0.7166	−0.0929	0.125*
C24	1.3773 (8)	0.75469 (13)	0.0789 (3)	0.0596 (12)
H24	1.4617	0.7293	0.1025	0.072*
C25	1.1997 (8)	0.77663 (13)	0.1365 (3)	0.0521 (10)
C26	1.1395 (11)	0.76031 (16)	0.2335 (3)	0.0799 (15)
H26A	1.1720	0.7840	0.2779	0.120*
H26B	1.2503	0.7351	0.2483	0.120*
H26C	0.9577	0.7514	0.2364	0.120*
N1	0.9123 (7)	0.84036 (11)	0.1610 (2)	0.0588 (9)
H1E	0.9165	0.8349	0.2204	0.071*
O1	−0.9091 (7)	1.15045 (11)	0.2223 (2)	0.0767 (9)
H1D	−0.8354	1.1383	0.1779	0.115*
O2	−0.5598 (6)	1.10083 (9)	0.14266 (17)	0.0608 (8)
O3	−0.2174 (6)	1.05188 (11)	0.06045 (18)	0.0716 (9)
H3A	−0.3365	1.0704	0.0648	0.107*
O4	−0.2717 (6)	1.03226 (10)	0.47874 (18)	0.0662 (9)
O5	0.2908 (5)	0.95260 (9)	0.25280 (17)	0.0572 (8)
O6	0.4665 (6)	0.86440 (11)	0.2613 (2)	0.0766 (9)
H6	0.3221	0.8590	0.2372	0.115*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.072 (3)	0.069 (3)	0.062 (3)	0.006 (2)	0.010 (2)	−0.009 (2)
C2	0.053 (3)	0.053 (3)	0.051 (3)	0.000 (2)	0.003 (2)	−0.006 (2)
C3	0.065 (3)	0.050 (3)	0.066 (3)	0.016 (2)	0.008 (2)	−0.004 (2)
C4	0.063 (3)	0.045 (2)	0.052 (3)	0.005 (2)	−0.001 (2)	0.0046 (19)
C5	0.047 (2)	0.043 (2)	0.047 (2)	0.0015 (19)	−0.0015 (18)	0.0008 (18)
C6	0.046 (2)	0.046 (2)	0.038 (2)	−0.0011 (18)	−0.0002 (17)	−0.0030 (17)
C7	0.055 (2)	0.056 (3)	0.040 (2)	0.000 (2)	0.0018 (19)	0.0014 (18)
C8	0.051 (2)	0.041 (2)	0.045 (2)	−0.0038 (19)	0.0000 (18)	0.0027 (18)
C9	0.051 (2)	0.038 (2)	0.040 (2)	−0.0008 (18)	0.0012 (18)	0.0020 (17)
C10	0.043 (2)	0.039 (2)	0.041 (2)	−0.0025 (18)	0.0010 (17)	0.0015 (17)
C11	0.044 (2)	0.052 (2)	0.042 (2)	0.0003 (19)	−0.0010 (18)	0.0057 (19)
C12	0.061 (3)	0.050 (2)	0.038 (2)	0.002 (2)	0.0015 (19)	0.0049 (18)
C13	0.060 (3)	0.055 (3)	0.040 (2)	0.004 (2)	0.0061 (19)	−0.0042 (19)
C14	0.049 (2)	0.042 (2)	0.046 (2)	0.002 (2)	−0.0009 (18)	0.0017 (18)
C15	0.050 (2)	0.047 (2)	0.037 (2)	0.0029 (19)	−0.0004 (17)	0.0010 (17)
C16	0.053 (2)	0.056 (3)	0.055 (3)	0.005 (2)	0.006 (2)	−0.006 (2)
C17	0.053 (2)	0.048 (2)	0.057 (2)	0.004 (2)	0.011 (2)	−0.0007 (19)
C18	0.050 (2)	0.057 (3)	0.053 (3)	0.005 (2)	0.001 (2)	−0.0040 (19)
C19	0.049 (2)	0.046 (2)	0.045 (2)	−0.0026 (19)	0.0024 (18)	−0.0039 (18)
C20	0.055 (2)	0.055 (3)	0.049 (2)	0.001 (2)	0.004 (2)	0.0003 (19)
C21	0.063 (3)	0.066 (3)	0.042 (2)	−0.005 (2)	0.011 (2)	−0.006 (2)
C22	0.050 (2)	0.058 (3)	0.060 (3)	−0.002 (2)	0.008 (2)	−0.009 (2)
C23	0.071 (3)	0.081 (4)	0.099 (4)	0.008 (3)	0.020 (3)	−0.015 (3)
C24	0.064 (3)	0.040 (2)	0.074 (3)	0.005 (2)	0.000 (2)	−0.003 (2)
C25	0.062 (3)	0.042 (2)	0.052 (2)	−0.002 (2)	0.000 (2)	0.0045 (19)
C26	0.118 (4)	0.062 (3)	0.059 (3)	0.002 (3)	0.005 (3)	0.014 (2)
N1	0.073 (2)	0.064 (2)	0.0389 (18)	0.015 (2)	0.0049 (17)	−0.0037 (16)
O1	0.094 (2)	0.077 (2)	0.0592 (19)	0.0371 (19)	−0.0034 (18)	0.0122 (17)
O2	0.080 (2)	0.0632 (19)	0.0397 (16)	0.0175 (16)	−0.0012 (14)	0.0092 (13)
O3	0.096 (3)	0.081 (2)	0.0376 (16)	0.0287 (18)	0.0062 (15)	0.0095 (14)
O4	0.078 (2)	0.082 (2)	0.0380 (16)	0.0233 (16)	0.0002 (14)	0.0067 (15)
O5	0.0615 (18)	0.0604 (18)	0.0498 (16)	0.0191 (15)	0.0021 (14)	−0.0034 (13)
O6	0.080 (2)	0.078 (2)	0.072 (2)	−0.0034 (18)	0.0101 (17)	0.0016 (17)

Geometric parameters (Å, º) top

C1—C2	1.498 (5)	C16—H16A	0.97
C1—H2D	0.96	C16—H16B	0.97
C1—H1B	0.96	C17—O6	1.392 (5)
C1—H1C	0.96	C17—C18	1.523 (5)
C2—C3	1.378 (5)	C17—H17	0.98
C2—C7	1.391 (5)	C18—N1	1.440 (5)
C3—C4	1.393 (5)	C18—H18A	0.97
C3—H3	0.93	C18—H18B	0.97
C4—O1	1.353 (4)	C19—C20	1.385 (5)
C4—C5	1.409 (5)	C19—N1	1.393 (5)
C5—C6	1.416 (5)	C19—C25	1.411 (5)
C5—C8	1.448 (5)	C20—C21	1.404 (5)
C6—C7	1.373 (5)	C20—H20	0.93
C6—C11	1.490 (5)	C21—C22	1.380 (6)
C7—H7	0.93	C21—H21	0.93
C8—O2	1.274 (4)	C22—C24	1.375 (5)
C8—C9	1.439 (5)	C22—C23	1.505 (6)
C9—C12	1.403 (5)	C23—H23A	0.96
C9—C10	1.417 (5)	C23—H23B	0.96
C10—C15	1.361 (5)	C23—H23C	0.96
C10—C11	1.487 (5)	C24—C25	1.385 (5)
C11—O4	1.207 (4)	C24—H24	0.93
C12—O3	1.358 (4)	C25—C26	1.496 (5)
C12—C13	1.379 (5)	C26—H26A	0.96
C13—C14	1.384 (5)	C26—H26B	0.96
C13—H13	0.93	C26—H26C	0.96
C14—O5	1.355 (4)	N1—H1E	0.86
C14—C15	1.405 (5)	O1—H1D	0.82
C15—H15	0.93	O3—H3A	0.82
C16—O5	1.445 (4)	O6—H6	0.82
C16—C17	1.505 (5)

C2—C1—H2D	109.5	C17—C16—H16B	110.4
C2—C1—H1B	109.5	H16A—C16—H16B	108.6
H2D—C1—H1B	109.5	O6—C17—C16	112.6 (3)
C2—C1—H1C	109.5	O6—C17—C18	111.0 (3)
H2D—C1—H1C	109.5	C16—C17—C18	109.3 (3)
H1B—C1—H1C	109.5	O6—C17—H17	107.9
C3—C2—C7	117.8 (4)	C16—C17—H17	107.9
C3—C2—C1	121.2 (4)	C18—C17—H17	107.9
C7—C2—C1	120.9 (4)	N1—C18—C17	109.1 (3)
C2—C3—C4	121.9 (4)	N1—C18—H18A	109.9
C2—C3—H3	119.0	C17—C18—H18A	109.9
C4—C3—H3	119.0	N1—C18—H18B	109.9
O1—C4—C3	117.5 (4)	C17—C18—H18B	109.9
O1—C4—C5	122.1 (4)	H18A—C18—H18B	108.3
C3—C4—C5	120.3 (4)	C20—C19—N1	121.9 (4)
C4—C5—C6	117.2 (3)	C20—C19—C25	118.8 (4)
C4—C5—C8	121.6 (3)	N1—C19—C25	119.2 (3)
C6—C5—C8	121.2 (3)	C19—C20—C21	120.5 (4)
C7—C6—C5	120.8 (4)	C19—C20—H20	119.8
C7—C6—C11	119.4 (3)	C21—C20—H20	119.8
C5—C6—C11	119.7 (3)	C22—C21—C20	121.4 (4)
C6—C7—C2	121.9 (4)	C22—C21—H21	119.3
C6—C7—H7	119.1	C20—C21—H21	119.3
C2—C7—H7	119.1	C24—C22—C21	117.0 (4)
O2—C8—C9	120.4 (3)	C24—C22—C23	121.3 (4)
O2—C8—C5	119.7 (3)	C21—C22—C23	121.8 (4)
C9—C8—C5	119.9 (3)	C22—C23—H23A	109.5
C12—C9—C10	117.3 (3)	C22—C23—H23B	109.5
C12—C9—C8	121.6 (3)	H23A—C23—H23B	109.5
C10—C9—C8	121.1 (3)	C22—C23—H23C	109.5
C15—C10—C9	121.5 (3)	H23A—C23—H23C	109.5
C15—C10—C11	118.4 (3)	H23B—C23—H23C	109.5
C9—C10—C11	120.1 (3)	C22—C24—C25	124.0 (4)
O4—C11—C10	121.2 (3)	C22—C24—H24	118.0
O4—C11—C6	120.7 (3)	C25—C24—H24	118.0
C10—C11—C6	118.0 (3)	C24—C25—C19	118.3 (4)
O3—C12—C13	117.2 (3)	C24—C25—C26	122.0 (4)
O3—C12—C9	121.2 (3)	C19—C25—C26	119.7 (4)
C13—C12—C9	121.6 (3)	C25—C26—H26A	109.5
C12—C13—C14	119.7 (3)	C25—C26—H26B	109.5
C12—C13—H13	120.2	H26A—C26—H26B	109.5
C14—C13—H13	120.2	C25—C26—H26C	109.5
O5—C14—C13	125.0 (3)	H26A—C26—H26C	109.5
O5—C14—C15	114.8 (3)	H26B—C26—H26C	109.5
C13—C14—C15	120.2 (3)	C19—N1—C18	121.8 (3)
C10—C15—C14	119.7 (3)	C19—N1—H1E	119.1
C10—C15—H15	120.1	C18—N1—H1E	119.1
C14—C15—H15	120.1	C4—O1—H1D	109.5
O5—C16—C17	106.6 (3)	C12—O3—H3A	109.5
O5—C16—H16A	110.4	C14—O5—C16	118.5 (3)
C17—C16—H16A	110.4	C17—O6—H6	109.5
O5—C16—H16B	110.4

C7—C2—C3—C4	−0.5 (6)	C10—C9—C12—O3	−179.4 (3)
C1—C2—C3—C4	−178.2 (4)	C8—C9—C12—O3	0.7 (6)
C2—C3—C4—O1	178.9 (4)	C10—C9—C12—C13	0.2 (6)
C2—C3—C4—C5	0.7 (6)	C8—C9—C12—C13	−179.6 (3)
O1—C4—C5—C6	−179.1 (4)	O3—C12—C13—C14	180.0 (4)
C3—C4—C5—C6	−0.9 (6)	C9—C12—C13—C14	0.3 (6)
O1—C4—C5—C8	−0.8 (6)	C12—C13—C14—O5	179.1 (3)
C3—C4—C5—C8	177.4 (4)	C12—C13—C14—C15	−1.0 (6)
C4—C5—C6—C7	1.1 (5)	C9—C10—C15—C14	−0.8 (5)
C8—C5—C6—C7	−177.3 (3)	C11—C10—C15—C14	179.5 (3)
C4—C5—C6—C11	−179.5 (3)	O5—C14—C15—C10	−178.8 (3)
C8—C5—C6—C11	2.1 (5)	C13—C14—C15—C10	1.3 (5)
C5—C6—C7—C2	−0.9 (6)	O5—C16—C17—O6	57.8 (4)
C11—C6—C7—C2	179.6 (3)	O5—C16—C17—C18	−178.3 (3)
C3—C2—C7—C6	0.6 (6)	O6—C17—C18—N1	−54.5 (4)
C1—C2—C7—C6	178.3 (4)	C16—C17—C18—N1	−179.3 (3)
C4—C5—C8—O2	0.7 (6)	N1—C19—C20—C21	174.2 (4)
C6—C5—C8—O2	179.0 (3)	C25—C19—C20—C21	−1.8 (6)
C4—C5—C8—C9	−179.1 (3)	C19—C20—C21—C22	−0.2 (6)
C6—C5—C8—C9	−0.8 (5)	C20—C21—C22—C24	1.8 (6)
O2—C8—C9—C12	−0.1 (5)	C20—C21—C22—C23	−177.1 (4)
C5—C8—C9—C12	179.7 (3)	C21—C22—C24—C25	−1.5 (6)
O2—C8—C9—C10	−179.9 (3)	C23—C22—C24—C25	177.5 (4)
C5—C8—C9—C10	−0.1 (5)	C22—C24—C25—C19	−0.5 (6)
C12—C9—C10—C15	0.0 (5)	C22—C24—C25—C26	179.3 (4)
C8—C9—C10—C15	179.9 (3)	C20—C19—C25—C24	2.1 (6)
C12—C9—C10—C11	179.8 (3)	N1—C19—C25—C24	−174.0 (3)
C8—C9—C10—C11	−0.4 (5)	C20—C19—C25—C26	−177.7 (4)
C15—C10—C11—O4	2.9 (5)	N1—C19—C25—C26	6.2 (6)
C9—C10—C11—O4	−176.8 (4)	C20—C19—N1—C18	15.6 (6)
C15—C10—C11—C6	−178.5 (3)	C25—C19—N1—C18	−168.4 (4)
C9—C10—C11—C6	1.7 (5)	C17—C18—N1—C19	−178.8 (3)
C7—C6—C11—O4	−4.6 (6)	C13—C14—O5—C16	−5.0 (5)
C5—C6—C11—O4	176.0 (4)	C15—C14—O5—C16	175.1 (3)
C7—C6—C11—C10	176.9 (3)	C17—C16—O5—C14	−176.9 (3)
C5—C6—C11—C10	−2.6 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1D···O2	0.82	1.86	2.575 (4)	145
O3—H3A···O2	0.82	1.83	2.556 (4)	147
O6—H6···N1ⁱ	0.82	2.40	3.218 (5)	177
C15—H15···O4ⁱⁱ	0.93	2.43	3.334 (4)	164

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

Experimental details

Crystal data
Chemical formula	C₂₆H₂₅NO₆
M_r	447.47
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	5.0668 (3), 29.7496 (17), 14.2201 (8)
β (°)	90.530 (4)
V (Å³)	2143.4 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.32 × 0.14 × 0.04

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker,2005)
T_min, T_max	0.969, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	17905, 4939, 2028
R_int	0.072
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.072, 0.232, 0.99
No. of reflections	4939
No. of parameters	305
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.65, −0.28

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1D···O2	0.82	1.86	2.575 (4)	145
O3—H3A···O2	0.82	1.83	2.556 (4)	147
O6—H6···N1ⁱ	0.82	2.40	3.218 (5)	177
C15—H15···O4ⁱⁱ	0.93	2.43	3.334 (4)	164

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

Acknowledgements

This project was supported by the Youth Award of Shandong Province (grant No. 2007BS03033) and the Natural Science Foundation of Shandong Province (grant No. Y2005C35).

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Srinivas, G., Anto, R. J., Srinivas, P., Vidhyalakshmi, S., Senan, V. P. & Karunagaran, D. (2003). Eur. J. Pharmacol. 473, 117–125. Web of Science CrossRef PubMed CAS Google Scholar
Teich, L., Daub, K. S., Krugel, V., Nissler, L., Gebhardt, R. & Eger, K. (2004). Bioorg. Med. Chem. 12, 5961–5971. Web of Science CSD CrossRef PubMed CAS Google Scholar
Wang, X.-P., Li, X., Wu, J.-F., Xu, W.-F. & Li, W.-L. (2006). Acta Cryst. E62, o4156–o4158. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wang, X.-P. & Xu, W.-F. (2005). Bull. Korean Chem. Soc. 26, 1923–1924. CAS Google Scholar

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Volume 65| Part 2| February 2009| Page o367

doi:10.1107/S1600536809002347

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

6-[3-(2,4-Di­methyl­anilino)-2-hy­droxy­prop­­oxy]-1,8-dihydr­­oxy-3-methyl-9,10-di­hydro­anthracene-9,10-dione

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

6-[3-(2,4-Dimethylanilino)-2-hydroxypropoxy]-1,8-dihydroxy-3-methyl-9,10-dihydroanthracene-9,10-dione