1,3,8-Trihydr­oxy-6-methyl­anthraquinone monohydrate

Zhu, J.-C.; Liang, Y.; Wang, H.-S.; Pan, Y.-M.; Zhang, Y.

doi:10.1107/S1600536806049178

1,3,8-Trihydroxy-6-methylanthraquinone monohydrate

J.-C. Zhu, Y. Liang, H.-S. Wang, Y.-M. Pan and Y. Zhang

The title compound, C₁₅H₁₀O₅·H₂O, also known as emodin monohydrate, was isolated from the roots of Polygonum cuspidatum Sieb. et Zucc. It is an anthraquinone derivative, and all of its non-H atoms are essentially coplanar. Intramolecular O—H

O hydrogen bonds and intermolecular O—H

O and C—H

O hydrogen bonds are observed in this crystal form. The crystal structure is further stabilized by weak π–π interactions and hydrogen bonds to the water molecule.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806049178/gh2013sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806049178/gh2013Isup2.hkl Contains datablock I

CCDC reference: 633852

checkCIF report

Key indicators

Single-crystal X-ray study
T = 153 K
Mean (C-C) = 0.005 Å
R factor = 0.080
wR factor = 0.168
Data-to-parameter ratio = 11.1

checkCIF/PLATON results

No syntax errors found





Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.728     0.983
            Tmin(prime) and Tmax expected:      0.964     0.983
            RR(prime) =      0.756
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.75
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT731_ALERT_1_C Bond    Calc     0.86(5), Rep     0.86(2) ......       2.50 su-Ra
              O6   -H6A     1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.86(5), Rep     0.85(2) ......       2.50 su-Ra
              O6   -H6B     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.86(5), Rep     0.86(2) ......       2.50 su-Ra
              O6   -H6A     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.86(5), Rep     0.85(2) ......       2.50 su-Ra
              O6   -H6B     1.555   1.555

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: CrystalClear (Rigaku, 1999); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXTL (Sheldrick, 2000) and PLATON (Spek, 2003).

1,3,8-Trihydroxy-6-methylanthraquinone monohydrate top

Crystal data top

C₁₅H₁₀O₅·H₂O	F(000) = 600
M_r = 288.25	D_x = 1.554 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybc	Cell parameters from 3018 reflections
a = 9.570 (3) Å	θ = 3.5–25.3°
b = 15.142 (3) Å	µ = 0.12 mm⁻¹
c = 9.245 (3) Å	T = 153 K
β = 113.140 (6)°	Block, orange
V = 1231.9 (6) Å³	0.30 × 0.14 × 0.14 mm
Z = 4

Data collection top

Rigaku Mercury diffractometer	2256 independent reflections
Radiation source: fine-focus sealed tube	1732 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.064
Detector resolution: 7.31 pixels mm^-1	θ_max = 25.3°, θ_min = 3.6°
ω scans	h = −10→11
Absorption correction: multi-scan (Jacobson, 1998)	k = −17→18
T_min = 0.728, T_max = 0.983	l = −11→11
11871 measured reflections

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)] = 0.080	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.168	H atoms treated by a mixture of independent and constrained refinement
S = 1.17	w = 1/[σ²(F_o²) + (0.0561P)² + 1.359P] where P = (F_o² + 2F_c²)/3
2256 reflections	(Δ/σ)_max = 0.001
203 parameters	Δρ_max = 0.36 e Å⁻³
2 restraints	Δρ_min = −0.24 e Å⁻³

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
O1	0.8799 (3)	0.07541 (14)	0.4666 (3)	0.0288 (6)
O2	0.8105 (3)	0.42744 (14)	0.4925 (3)	0.0326 (6)
O3	0.6639 (3)	0.04776 (14)	0.5600 (3)	0.0334 (6)
H3	0.7320	0.0340	0.5281	0.050*
O4	0.4300 (3)	0.29036 (16)	0.6820 (3)	0.0327 (6)
H4	0.4309	0.3458	0.6843	0.049*
O5	1.0916 (3)	0.09803 (15)	0.3627 (3)	0.0322 (6)
H5	1.0321	0.0689	0.3911	0.048*
O6	0.5802 (4)	0.53768 (19)	0.2925 (4)	0.0459 (8)
H6A	0.654 (5)	0.516 (4)	0.371 (5)	0.09 (2)*
H6B	0.582 (9)	0.528 (5)	0.202 (4)	0.16 (3)*
C1	0.8635 (4)	0.1582 (2)	0.4716 (4)	0.0225 (7)
C2	0.7498 (3)	0.1937 (2)	0.5229 (4)	0.0205 (7)
C3	0.7312 (3)	0.2851 (2)	0.5335 (4)	0.0215 (7)
C4	0.8276 (4)	0.3473 (2)	0.4880 (4)	0.0220 (7)
C5	0.9428 (3)	0.3102 (2)	0.4353 (4)	0.0204 (7)
C6	0.9588 (3)	0.2178 (2)	0.4266 (4)	0.0198 (7)
C7	0.6544 (4)	0.1371 (2)	0.5655 (4)	0.0249 (8)
C8	0.5475 (4)	0.1713 (2)	0.6169 (4)	0.0280 (8)
H8	0.4839	0.1326	0.6447	0.034*
C9	0.5336 (4)	0.2612 (2)	0.6276 (4)	0.0254 (8)
C10	0.6256 (4)	0.3193 (2)	0.5851 (4)	0.0254 (8)
H10	0.6150	0.3814	0.5918	0.030*
C11	1.0683 (4)	0.1855 (2)	0.3750 (4)	0.0248 (7)
C12	1.1571 (4)	0.2440 (2)	0.3304 (4)	0.0271 (8)
H12	1.2293	0.2213	0.2931	0.033*
C13	1.1417 (4)	0.3344 (2)	0.3398 (4)	0.0243 (7)
C14	1.0330 (4)	0.3673 (2)	0.3925 (4)	0.0251 (8)
H14	1.0212	0.4293	0.3990	0.030*
C15	1.2403 (4)	0.3964 (2)	0.2936 (4)	0.0320 (8)
H15A	1.3473	0.3861	0.3615	0.048*
H15B	1.2132	0.4575	0.3056	0.048*
H15C	1.2247	0.3857	0.1837	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0352 (13)	0.0182 (12)	0.0400 (15)	0.0008 (10)	0.0224 (12)	−0.0012 (10)
O2	0.0359 (14)	0.0197 (13)	0.0491 (16)	0.0003 (10)	0.0239 (13)	−0.0020 (11)
O3	0.0383 (14)	0.0213 (13)	0.0515 (17)	0.0003 (11)	0.0295 (13)	0.0017 (11)
O4	0.0322 (13)	0.0336 (14)	0.0390 (15)	0.0036 (11)	0.0213 (12)	−0.0007 (12)
O5	0.0385 (14)	0.0240 (13)	0.0449 (16)	0.0042 (11)	0.0280 (13)	0.0001 (11)
O6	0.0544 (19)	0.0411 (17)	0.045 (2)	0.0133 (15)	0.0224 (17)	−0.0016 (15)
C1	0.0244 (16)	0.0207 (17)	0.0214 (17)	0.0011 (14)	0.0077 (15)	−0.0008 (13)
C2	0.0191 (15)	0.0227 (17)	0.0192 (17)	0.0003 (13)	0.0068 (14)	0.0015 (13)
C3	0.0199 (16)	0.0244 (17)	0.0194 (17)	0.0015 (13)	0.0070 (14)	−0.0007 (13)
C4	0.0246 (16)	0.0202 (18)	0.0208 (17)	0.0016 (13)	0.0084 (14)	−0.0001 (13)
C5	0.0184 (15)	0.0233 (17)	0.0188 (17)	0.0015 (13)	0.0066 (14)	0.0007 (13)
C6	0.0199 (15)	0.0199 (17)	0.0207 (17)	0.0010 (13)	0.0091 (14)	0.0019 (13)
C7	0.0234 (17)	0.0263 (18)	0.0249 (18)	0.0042 (14)	0.0093 (15)	0.0030 (14)
C8	0.0269 (18)	0.030 (2)	0.031 (2)	0.0006 (15)	0.0161 (16)	0.0044 (15)
C9	0.0221 (16)	0.033 (2)	0.0236 (18)	0.0041 (15)	0.0113 (15)	0.0006 (15)
C10	0.0275 (17)	0.0232 (18)	0.0256 (18)	0.0048 (14)	0.0107 (16)	−0.0007 (14)
C11	0.0288 (17)	0.0231 (18)	0.0221 (18)	0.0022 (14)	0.0095 (15)	−0.0012 (14)
C12	0.0254 (17)	0.035 (2)	0.0232 (18)	0.0011 (15)	0.0119 (15)	−0.0017 (15)
C13	0.0244 (17)	0.0258 (18)	0.0225 (18)	−0.0013 (14)	0.0090 (15)	0.0023 (14)
C14	0.0270 (17)	0.0229 (17)	0.0247 (18)	0.0012 (14)	0.0094 (15)	0.0007 (14)
C15	0.0329 (19)	0.033 (2)	0.033 (2)	−0.0031 (16)	0.0165 (17)	0.0023 (16)

Geometric parameters (Å, º) top

O1—C1	1.266 (4)	C5—C14	1.385 (4)
O2—C4	1.227 (4)	C5—C6	1.414 (4)
O3—C7	1.358 (4)	C6—C11	1.399 (4)
O3—H3	0.8400	C7—C8	1.387 (4)
O4—C9	1.350 (4)	C8—C9	1.376 (5)
O4—H4	0.8400	C8—H8	0.9500
O5—C11	1.355 (4)	C9—C10	1.405 (4)
O5—H5	0.8400	C10—H10	0.9500
O6—H6A	0.86 (2)	C11—C12	1.397 (5)
O6—H6B	0.85 (2)	C12—C13	1.383 (5)
C1—C2	1.450 (4)	C12—H12	0.9500
C1—C6	1.455 (4)	C13—C14	1.402 (5)
C2—C3	1.404 (4)	C13—C15	1.507 (4)
C2—C7	1.416 (4)	C14—H14	0.9500
C3—C10	1.376 (4)	C15—H15A	0.9800
C3—C4	1.491 (4)	C15—H15B	0.9800
C4—C5	1.481 (4)	C15—H15C	0.9800

C7—O3—H3	109.5	C9—C8—H8	120.0
C9—O4—H4	109.5	C7—C8—H8	120.0
C11—O5—H5	109.5	O4—C9—C8	117.1 (3)
H6A—O6—H6B	116 (6)	O4—C9—C10	122.2 (3)
O1—C1—C2	119.9 (3)	C8—C9—C10	120.7 (3)
O1—C1—C6	120.2 (3)	C3—C10—C9	119.2 (3)
C2—C1—C6	119.9 (3)	C3—C10—H10	120.4
C3—C2—C7	117.6 (3)	C9—C10—H10	120.4
C3—C2—C1	121.4 (3)	O5—C11—C12	117.1 (3)
C7—C2—C1	121.0 (3)	O5—C11—C6	122.7 (3)
C10—C3—C2	121.7 (3)	C12—C11—C6	120.2 (3)
C10—C3—C4	118.7 (3)	C13—C12—C11	121.1 (3)
C2—C3—C4	119.6 (3)	C13—C12—H12	119.4
O2—C4—C5	120.9 (3)	C11—C12—H12	119.4
O2—C4—C3	120.6 (3)	C12—C13—C14	119.1 (3)
C5—C4—C3	118.5 (3)	C12—C13—C15	120.3 (3)
C14—C5—C6	120.6 (3)	C14—C13—C15	120.6 (3)
C14—C5—C4	119.0 (3)	C5—C14—C13	120.5 (3)
C6—C5—C4	120.4 (3)	C5—C14—H14	119.7
C11—C6—C5	118.5 (3)	C13—C14—H14	119.7
C11—C6—C1	121.2 (3)	C13—C15—H15A	109.5
C5—C6—C1	120.3 (3)	C13—C15—H15B	109.5
O3—C7—C8	117.0 (3)	H15A—C15—H15B	109.5
O3—C7—C2	122.2 (3)	C13—C15—H15C	109.5
C8—C7—C2	120.8 (3)	H15A—C15—H15C	109.5
C9—C8—C7	119.9 (3)	H15B—C15—H15C	109.5

O1—C1—C2—C3	178.4 (3)	C3—C2—C7—O3	−179.7 (3)
C6—C1—C2—C3	−1.3 (5)	C1—C2—C7—O3	−0.3 (5)
O1—C1—C2—C7	−1.1 (5)	C3—C2—C7—C8	−0.5 (5)
C6—C1—C2—C7	179.2 (3)	C1—C2—C7—C8	179.0 (3)
C7—C2—C3—C10	0.8 (5)	O3—C7—C8—C9	179.0 (3)
C1—C2—C3—C10	−178.7 (3)	C2—C7—C8—C9	−0.3 (5)
C7—C2—C3—C4	−179.2 (3)	C7—C8—C9—O4	−178.4 (3)
C1—C2—C3—C4	1.3 (5)	C7—C8—C9—C10	0.8 (5)
C10—C3—C4—O2	−1.9 (5)	C2—C3—C10—C9	−0.3 (5)
C2—C3—C4—O2	178.1 (3)	C4—C3—C10—C9	179.7 (3)
C10—C3—C4—C5	178.9 (3)	O4—C9—C10—C3	178.7 (3)
C2—C3—C4—C5	−1.1 (4)	C8—C9—C10—C3	−0.5 (5)
O2—C4—C5—C14	0.8 (5)	C5—C6—C11—O5	−179.9 (3)
C3—C4—C5—C14	179.9 (3)	C1—C6—C11—O5	0.5 (5)
O2—C4—C5—C6	−178.3 (3)	C5—C6—C11—C12	−1.2 (5)
C3—C4—C5—C6	0.9 (4)	C1—C6—C11—C12	179.1 (3)
C14—C5—C6—C11	0.4 (5)	O5—C11—C12—C13	−179.7 (3)
C4—C5—C6—C11	179.5 (3)	C6—C11—C12—C13	1.6 (5)
C14—C5—C6—C1	−179.9 (3)	C11—C12—C13—C14	−1.1 (5)
C4—C5—C6—C1	−0.9 (5)	C11—C12—C13—C15	179.0 (3)
O1—C1—C6—C11	1.0 (5)	C6—C5—C14—C13	0.0 (5)
C2—C1—C6—C11	−179.3 (3)	C4—C5—C14—C13	−179.0 (3)
O1—C1—C6—C5	−178.6 (3)	C12—C13—C14—C5	0.3 (5)
C2—C1—C6—C5	1.0 (4)	C15—C13—C14—C5	−179.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1	0.84	1.83	2.568 (3)	146
O3—H3···O5ⁱ	0.84	2.55	3.090 (3)	123
O4—H4···O6ⁱⁱ	0.84	1.79	2.620 (4)	172
O5—H5···O1	0.84	1.85	2.583 (3)	145
O5—H5···O1ⁱ	0.84	2.52	3.021 (3)	119
O6—H6A···O2	0.86 (2)	1.99 (3)	2.804 (4)	158 (5)
O6—H6B···O3ⁱⁱⁱ	0.85 (2)	2.11 (4)	2.879 (4)	149 (7)
C12—H12···O4^iv	0.95	2.51	3.434 (4)	163

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

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1,3,8-Trihydr­oxy-6-methyl­anthraquinone monohydrate

Supporting information

Key indicators

checkCIF/PLATON results

1,3,8-Trihydroxy-6-methylanthraquinone monohydrate