4-(1,1-Dimethyl­prop-2-en­yl)-1,3,5,6-tetra­hydr­oxy-2-(3-methyl­but-2-en­yl)-9H-xanthen-9-one monohydrate

The title compound, C₂₃H₂₄O₆·H₂O, a xanthone compound, was isolated from Cratoxylum formosum ssp. pruniflorum. The three rings in the mol­ecule are coplanar. The 3-methyl­but-2-enyl and 1,1-dimethyl­prop-2-enyl side chains are axially attached to the benzene ring. There are intra- and inter­molecular O—H...O and C—H...O inter­actions. The crystal structure is stabilized by these inter­molecular inter­actions as well by C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 297 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.055
• wR factor = 0.152
• Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT420_ALERT_2_B D-H Without Acceptor       O1W    -   H1W1   ...          ?
PLAT420_ALERT_2_B D-H Without Acceptor       O2     -   H2     ...          ?

Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.749     0.994
            Tmin(prime) and Tmax expected:      0.956     0.994
            RR(prime) =      0.784
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.78
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.34 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.14 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C19
PLAT480_ALERT_4_C Long H...A H-Bond Reported H17C   ..  CG1     ..       2.94 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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
   2 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

4-(1,1-Dimethylprop-2-enyl)-1,3,5,6-tetrahydroxy-2-(3-methylbut-2-enyl)-9H- xanthen-9-one monohydrate

Crystal data

C23H24O6·H2O	F(000) = 880
Mr = 414.44	Dx = 1.315 Mg m^−3
Monoclinic, P21/c	Melting point = 453–454 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.0244 (6) Å	Cell parameters from 4101 reflections
b = 19.7901 (11) Å	θ = 2.1–26.0°
c = 11.7645 (5) Å	µ = 0.10 mm^−1
β = 116.217 (4)°	T = 297 K
V = 2093.8 (2) Å^3	Plate, yellow
Z = 4	0.46 × 0.20 × 0.06 mm

Data collection

Siemens SMART CCD area-detector diffractometer	4101 independent reflections
Radiation source: fine-focus sealed tube	3319 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
Detector resolution: 8.33 pixels mm^-1	θmax = 26.0°, θmin = 2.1°
ω scans	h = −11→12
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −24→17
Tmin = 0.749, Tmax = 0.994	l = −14→13
11308 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.152	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0702P)^2 + 0.7399P] where P = (Fo^2 + 2Fc^2)/3
4101 reflections	(Δ/σ)max < 0.001
288 parameters	Δρmax = 0.44 e Å^−3
3 restraints	Δρmin = −0.25 e Å^−3

Special details

Experimental. Siemens SMART CCD area-detector

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. Owing to a large fraction of weak data at higher angles, the 2θ maximum was limited to 52°. 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 (Ų)

	x	y	z	Uiso*/Ueq
O1	1.23181 (14)	0.57717 (8)	0.39778 (14)	0.0480 (4)
H1	1.1710	0.5574	0.3350	0.057 (7)*
O2	1.26032 (16)	0.69255 (9)	0.75338 (16)	0.0563 (5)
H2	1.219 (3)	0.6996 (16)	0.799 (3)	0.096 (11)*
O3	0.80263 (13)	0.58954 (7)	0.47681 (12)	0.0384 (3)
O4	0.52590 (15)	0.56920 (8)	0.43013 (14)	0.0528 (4)
H4	0.4352	0.5661	0.4005	0.079*
O5	0.33623 (15)	0.50194 (8)	0.22007 (15)	0.0541 (4)
H5	0.2887	0.4805	0.1549	0.081*
O6	0.98240 (15)	0.52713 (8)	0.24345 (14)	0.0504 (4)
C1	1.16539 (18)	0.59794 (10)	0.46984 (18)	0.0342 (4)
C2	1.24646 (19)	0.63380 (9)	0.57879 (18)	0.0340 (4)
C3	1.1733 (2)	0.65522 (10)	0.65007 (18)	0.0370 (4)
C4	1.0235 (2)	0.64152 (10)	0.62029 (18)	0.0366 (4)
C5	0.94835 (18)	0.60405 (9)	0.50976 (17)	0.0327 (4)
C6	1.01336 (19)	0.58179 (9)	0.43186 (17)	0.0332 (4)
C7	0.9274 (2)	0.54480 (10)	0.31663 (18)	0.0357 (4)
C8	0.77471 (19)	0.52946 (9)	0.28839 (17)	0.0330 (4)
C9	0.71916 (19)	0.55325 (9)	0.37031 (17)	0.0322 (4)
C10	0.5722 (2)	0.54307 (10)	0.34738 (18)	0.0359 (4)
C11	0.47940 (19)	0.50796 (10)	0.23890 (19)	0.0377 (4)
C12	0.5338 (2)	0.48176 (10)	0.15803 (18)	0.0389 (5)
H12	0.4716	0.4567	0.0876	0.047*
C13	0.6790 (2)	0.49261 (10)	0.18161 (18)	0.0377 (4)
H13	0.7141	0.4754	0.1264	0.045*
C14	1.40985 (19)	0.64976 (9)	0.62209 (18)	0.0356 (4)
H14A	1.4594	0.6510	0.7140	0.043*
H14B	1.4546	0.6138	0.5946	0.043*
C15	1.43526 (19)	0.71577 (10)	0.57193 (19)	0.0377 (4)
H15	1.3973	0.7192	0.4843	0.045*
C16	1.5051 (2)	0.76946 (10)	0.6377 (2)	0.0457 (5)
C17	1.5244 (3)	0.83165 (13)	0.5729 (3)	0.0688 (7)
H17A	1.4794	0.8244	0.4829	0.103*
H17B	1.6285	0.8408	0.6024	0.103*
H17C	1.4776	0.8694	0.5919	0.103*
C18	1.5726 (3)	0.77431 (14)	0.7793 (2)	0.0691 (7)
H18A	1.5699	0.7308	0.8142	0.104*
H18B	1.5172	0.8061	0.8033	0.104*
H18C	1.6739	0.7892	0.8112	0.104*
C19	0.9548 (2)	0.67049 (11)	0.7056 (2)	0.0469 (5)
C20	1.0527 (3)	0.65138 (16)	0.8420 (2)	0.0644 (7)
H20	1.0824	0.6064	0.8565	0.077*
C21	1.1010 (3)	0.6907 (2)	0.9427 (3)	0.1079 (14)
H21A	1.0751	0.7361	0.9342	0.129*
H21B	1.1612	0.6729	1.0223	0.129*
C22	0.8027 (2)	0.64161 (15)	0.6833 (2)	0.0658 (8)
H22A	0.7758	0.6588	0.7467	0.099*
H22B	0.8084	0.5932	0.6885	0.099*
H22C	0.7290	0.6548	0.6009	0.099*
C23	0.9368 (4)	0.74748 (14)	0.6844 (4)	0.0898 (10)
H23A	0.8968	0.7664	0.7380	0.135*
H23B	0.8704	0.7565	0.5974	0.135*
H23C	1.0320	0.7674	0.7047	0.135*
H1W1	0.100 (4)	0.4055 (15)	0.021 (4)	0.122 (15)*
H2W1	0.111 (5)	0.450 (3)	−0.062 (2)	0.17 (2)*
O1W	0.1526 (3)	0.4351 (2)	0.0119 (2)	0.1228 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0268 (7)	0.0732 (10)	0.0476 (8)	−0.0095 (6)	0.0197 (6)	−0.0204 (7)
O2	0.0386 (8)	0.0752 (11)	0.0593 (10)	−0.0232 (7)	0.0253 (7)	−0.0353 (9)
O3	0.0244 (6)	0.0513 (8)	0.0411 (7)	−0.0074 (5)	0.0159 (6)	−0.0127 (6)
O4	0.0277 (7)	0.0817 (11)	0.0540 (9)	−0.0137 (7)	0.0228 (7)	−0.0220 (8)
O5	0.0289 (7)	0.0788 (11)	0.0537 (9)	−0.0189 (7)	0.0174 (7)	−0.0178 (8)
O6	0.0335 (7)	0.0762 (11)	0.0450 (8)	−0.0072 (7)	0.0205 (6)	−0.0201 (7)
C1	0.0261 (9)	0.0387 (10)	0.0399 (10)	−0.0006 (7)	0.0165 (8)	−0.0017 (8)
C2	0.0258 (9)	0.0337 (10)	0.0418 (10)	−0.0033 (7)	0.0145 (8)	0.0008 (8)
C3	0.0302 (9)	0.0390 (10)	0.0419 (11)	−0.0054 (8)	0.0158 (8)	−0.0072 (8)
C4	0.0308 (9)	0.0389 (11)	0.0426 (11)	−0.0026 (8)	0.0184 (8)	−0.0062 (8)
C5	0.0232 (8)	0.0358 (10)	0.0394 (10)	−0.0017 (7)	0.0142 (7)	−0.0009 (8)
C6	0.0258 (8)	0.0360 (10)	0.0375 (10)	−0.0013 (7)	0.0136 (8)	−0.0014 (8)
C7	0.0281 (9)	0.0421 (11)	0.0372 (10)	0.0003 (8)	0.0148 (8)	−0.0026 (8)
C8	0.0284 (9)	0.0342 (10)	0.0350 (10)	−0.0003 (7)	0.0127 (7)	−0.0002 (8)
C9	0.0262 (8)	0.0340 (9)	0.0342 (10)	−0.0025 (7)	0.0112 (7)	−0.0007 (7)
C10	0.0297 (9)	0.0406 (10)	0.0392 (10)	−0.0045 (8)	0.0168 (8)	−0.0016 (8)
C11	0.0262 (9)	0.0420 (11)	0.0412 (11)	−0.0073 (8)	0.0115 (8)	0.0023 (8)
C12	0.0339 (10)	0.0412 (11)	0.0351 (10)	−0.0066 (8)	0.0094 (8)	−0.0049 (8)
C13	0.0334 (10)	0.0415 (11)	0.0377 (10)	−0.0006 (8)	0.0151 (8)	−0.0051 (8)
C14	0.0244 (8)	0.0391 (10)	0.0418 (10)	−0.0038 (7)	0.0133 (7)	−0.0047 (8)
C15	0.0282 (9)	0.0438 (11)	0.0401 (10)	−0.0026 (8)	0.0142 (8)	−0.0010 (8)
C16	0.0424 (11)	0.0419 (11)	0.0536 (13)	−0.0054 (9)	0.0221 (10)	−0.0041 (10)
C17	0.0781 (18)	0.0504 (15)	0.0734 (18)	−0.0157 (13)	0.0293 (14)	0.0002 (12)
C18	0.0868 (18)	0.0608 (16)	0.0610 (16)	−0.0264 (14)	0.0337 (14)	−0.0196 (13)
C19	0.0356 (10)	0.0548 (13)	0.0543 (13)	−0.0056 (9)	0.0236 (9)	−0.0180 (10)
C20	0.0418 (12)	0.104 (2)	0.0543 (14)	−0.0088 (13)	0.0272 (11)	−0.0232 (14)
C21	0.0690 (19)	0.190 (4)	0.072 (2)	−0.044 (2)	0.0382 (16)	−0.063 (2)
C22	0.0413 (12)	0.103 (2)	0.0630 (15)	−0.0125 (12)	0.0316 (11)	−0.0320 (14)
C23	0.109 (2)	0.0618 (18)	0.131 (3)	0.0083 (17)	0.082 (2)	−0.0157 (18)
O1W	0.0961 (17)	0.205 (3)	0.0545 (13)	−0.085 (2)	0.0214 (13)	−0.0182 (17)

Geometric parameters (Å, º)

O1—C1	1.353 (2)	C14—C15	1.501 (3)
O1—H1	0.8200	C14—H14A	0.9700
O2—C3	1.359 (2)	C14—H14B	0.9700
O2—H2	0.83 (3)	C15—C16	1.319 (3)
O3—C9	1.364 (2)	C15—H15	0.9300
O3—C5	1.366 (2)	C16—C18	1.499 (3)
O4—C10	1.352 (2)	C16—C17	1.505 (3)
O4—H4	0.8200	C17—H17A	0.9600
O5—C11	1.357 (2)	C17—H17B	0.9600
O5—H5	0.8200	C17—H17C	0.9600
O6—C7	1.260 (2)	C18—H18A	0.9600
C1—C2	1.374 (3)	C18—H18B	0.9600
C1—C6	1.422 (2)	C18—H18C	0.9600
C2—C3	1.401 (3)	C19—C20	1.513 (3)
C2—C14	1.518 (2)	C19—C22	1.539 (3)
C3—C4	1.410 (3)	C19—C23	1.541 (4)
C4—C5	1.394 (3)	C20—C21	1.318 (4)
C4—C19	1.556 (3)	C20—H20	0.9300
C5—C6	1.409 (3)	C21—H21A	0.9300
C6—C7	1.444 (3)	C21—H21B	0.9300
C7—C8	1.448 (2)	C22—H22A	0.9600
C8—C9	1.391 (3)	C22—H22B	0.9600
C8—C13	1.402 (3)	C22—H22C	0.9600
C9—C10	1.391 (2)	C23—H23A	0.9600
C10—C11	1.388 (3)	C23—H23B	0.9600
C11—C12	1.389 (3)	C23—H23C	0.9600
C12—C13	1.372 (3)	O1W—H1W1	0.83 (4)
C12—H12	0.9300	O1W—H2W1	0.83 (3)
C13—H13	0.9300
C1—O1—H1	109.5	C15—C14—H14B	108.9
C3—O2—H2	111 (2)	C2—C14—H14B	108.9
C9—O3—C5	121.11 (14)	H14A—C14—H14B	107.7
C10—O4—H4	109.5	C16—C15—C14	127.52 (19)
C11—O5—H5	109.5	C16—C15—H15	116.2
O1—C1—C2	119.33 (15)	C14—C15—H15	116.2
O1—C1—C6	119.38 (16)	C15—C16—C18	124.4 (2)
C2—C1—C6	121.29 (17)	C15—C16—C17	121.0 (2)
C1—C2—C3	117.68 (16)	C18—C16—C17	114.5 (2)
C1—C2—C14	121.77 (17)	C16—C17—H17A	109.5
C3—C2—C14	120.55 (16)	C16—C17—H17B	109.5
O2—C3—C2	113.65 (16)	H17A—C17—H17B	109.5
O2—C3—C4	121.27 (17)	C16—C17—H17C	109.5
C2—C3—C4	125.07 (17)	H17A—C17—H17C	109.5
C5—C4—C3	114.31 (17)	H17B—C17—H17C	109.5
C5—C4—C19	125.93 (16)	C16—C18—H18A	109.5
C3—C4—C19	119.71 (16)	C16—C18—H18B	109.5
O3—C5—C4	116.49 (16)	H18A—C18—H18B	109.5
O3—C5—C6	119.57 (16)	C16—C18—H18C	109.5
C4—C5—C6	123.93 (16)	H18A—C18—H18C	109.5
C5—C6—C1	117.69 (16)	H18B—C18—H18C	109.5
C5—C6—C7	120.90 (16)	C20—C19—C22	102.55 (19)
C1—C6—C7	121.41 (17)	C20—C19—C23	113.1 (2)
O6—C7—C6	121.51 (16)	C22—C19—C23	107.7 (2)
O6—C7—C8	121.50 (17)	C20—C19—C4	109.09 (17)
C6—C7—C8	116.98 (16)	C22—C19—C4	116.19 (17)
C9—C8—C13	118.15 (16)	C23—C19—C4	108.3 (2)
C9—C8—C7	118.45 (16)	C21—C20—C19	127.9 (3)
C13—C8—C7	123.39 (17)	C21—C20—H20	116.0
O3—C9—C10	114.97 (16)	C19—C20—H20	116.0
O3—C9—C8	122.95 (15)	C20—C21—H21A	120.0
C10—C9—C8	122.07 (16)	C20—C21—H21B	120.0
O4—C10—C11	123.34 (16)	H21A—C21—H21B	120.0
O4—C10—C9	118.42 (16)	C19—C22—H22A	109.5
C11—C10—C9	118.22 (18)	C19—C22—H22B	109.5
O5—C11—C10	115.12 (18)	H22A—C22—H22B	109.5
O5—C11—C12	124.21 (17)	C19—C22—H22C	109.5
C10—C11—C12	120.67 (17)	H22A—C22—H22C	109.5
C13—C12—C11	120.34 (17)	H22B—C22—H22C	109.5
C13—C12—H12	119.8	C19—C23—H23A	109.5
C11—C12—H12	119.8	C19—C23—H23B	109.5
C12—C13—C8	120.49 (18)	H23A—C23—H23B	109.5
C12—C13—H13	119.8	C19—C23—H23C	109.5
C8—C13—H13	119.8	H23A—C23—H23C	109.5
C15—C14—C2	113.24 (15)	H23B—C23—H23C	109.5
C15—C14—H14A	108.9	H1W1—O1W—H2W1	109 (4)
C2—C14—H14A	108.9
O1—C1—C2—C3	179.17 (17)	C5—O3—C9—C10	−179.11 (16)
C6—C1—C2—C3	−1.3 (3)	C5—O3—C9—C8	−0.7 (3)
O1—C1—C2—C14	−1.1 (3)	C13—C8—C9—O3	179.97 (16)
C6—C1—C2—C14	178.38 (17)	C7—C8—C9—O3	−0.9 (3)
C1—C2—C3—O2	−177.54 (18)	C13—C8—C9—C10	−1.7 (3)
C14—C2—C3—O2	2.8 (3)	C7—C8—C9—C10	177.38 (17)
C1—C2—C3—C4	1.5 (3)	O3—C9—C10—O4	0.0 (3)
C14—C2—C3—C4	−178.15 (18)	C8—C9—C10—O4	−178.46 (17)
O2—C3—C4—C5	178.48 (18)	O3—C9—C10—C11	178.43 (16)
C2—C3—C4—C5	−0.5 (3)	C8—C9—C10—C11	0.0 (3)
O2—C3—C4—C19	1.0 (3)	O4—C10—C11—O5	0.6 (3)
C2—C3—C4—C19	−177.99 (19)	C9—C10—C11—O5	−177.76 (17)
C9—O3—C5—C4	179.92 (16)	O4—C10—C11—C12	−179.41 (18)
C9—O3—C5—C6	0.7 (3)	C9—C10—C11—C12	2.2 (3)
C3—C4—C5—O3	−179.93 (16)	O5—C11—C12—C13	177.30 (18)
C19—C4—C5—O3	−2.7 (3)	C10—C11—C12—C13	−2.7 (3)
C3—C4—C5—C6	−0.7 (3)	C11—C12—C13—C8	0.9 (3)
C19—C4—C5—C6	176.56 (19)	C9—C8—C13—C12	1.3 (3)
O3—C5—C6—C1	−179.92 (16)	C7—C8—C13—C12	−177.77 (18)
C4—C5—C6—C1	0.9 (3)	C1—C2—C14—C15	90.6 (2)
O3—C5—C6—C7	1.0 (3)	C3—C2—C14—C15	−89.7 (2)
C4—C5—C6—C7	−178.19 (18)	C2—C14—C15—C16	117.7 (2)
O1—C1—C6—C5	179.70 (17)	C14—C15—C16—C18	−0.6 (4)
C2—C1—C6—C5	0.2 (3)	C14—C15—C16—C17	178.6 (2)
O1—C1—C6—C7	−1.2 (3)	C5—C4—C19—C20	130.3 (2)
C2—C1—C6—C7	179.26 (18)	C3—C4—C19—C20	−52.6 (3)
C5—C6—C7—O6	176.93 (18)	C5—C4—C19—C22	15.0 (3)
C1—C6—C7—O6	−2.1 (3)	C3—C4—C19—C22	−167.9 (2)
C5—C6—C7—C8	−2.5 (3)	C5—C4—C19—C23	−106.2 (3)
C1—C6—C7—C8	178.44 (17)	C3—C4—C19—C23	70.9 (3)
O6—C7—C8—C9	−177.01 (18)	C22—C19—C20—C21	−103.6 (3)
C6—C7—C8—C9	2.4 (3)	C23—C19—C20—C21	12.0 (4)
O6—C7—C8—C13	2.1 (3)	C4—C19—C20—C21	132.6 (3)
C6—C7—C8—C13	−178.49 (17)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O6	0.82	1.81	2.553 (2)	149
O4—H4···O1^i	0.82	2.04	2.805 (2)	156
O4—H4···O5	0.82	2.29	2.710 (2)	112
O5—H5···O1W	0.82	1.86	2.674 (3)	170
O1W—H2W1···O6^ii	0.83 (3)	1.97 (2)	2.797 (3)	172 (5)
C14—H14B···O4^iii	0.97	2.50	3.364 (3)	148
C23—H23C···O2	0.96	2.57	3.167 (5)	121
C17—H17C···Cg1^iv	0.96	2.94	3.595 (3)	129

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