6-[3-(2,4-Dimethyl-anilino)-2-hydroxy-prop-oxy]-1,8-dihydr-oxy-3-methyl-9,10-dihydro-anthracene-9,10-dione.

In the title compound, C(26)H(25)NO(6), the anthraquinone ring system forms a dihedral angle of 15.5 (1)° with the benzene ring of the dimethyl-aniline group. Intra-molecular O-H⋯O hydrogen bonding is observed between the carbonyl and two hydroxyl groups. The mol-ecules 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 = 447.47

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.072

wR(F 2) = 0.232

S = 0.99

4939 reflections

305 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.65 e Å−3

Δρmin = −0.28 e Å−3

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 ▶).

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

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

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

C26H25NO6	F(000) = 944
Mr = 447.47	Dx = 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

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

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(Fo2) + (0.11P)2] where P = (Fo2 + 2Fc2)/3
4939 reflections	(Δ/σ)max = 0.001
305 parameters	Δρmax = 0.65 e Å−3
1 restraint	Δρmin = −0.28 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .