2-(3,7-Dimethyl­octa-2,6-dien­yl)-1,3,5,8-tetra­hydroxyxanthone

The title compound, C₂₃H₂₄O₆, a xanthone derivative, was isolated from Garcinia polyantha Oliver. The orientation of the 3,7-dimethyl­octa-2,6-dienyl substituent with respect to the xanthone ring system is (+)synclinal. The crystal packing is stabilized by O—H...O and C—H...O inter­molecular hydrogen bonds and π–π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.056
• wR factor = 0.165
• Data-to-parameter ratio = 12.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.07 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.20 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C7'
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         18

   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

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


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

Author Response: M.I. Choudhary and S. Anjum are supervisors of the research students R. Swaleh, A. M. Lannang and S. Ali. H.-K. Fun is involved in the x-ray structure determination. All are involved in the research findings presented in this paper and also in the writing of the manuscript.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

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).

2-(3,7-Dimethylocta-2,6-dienyl)-1,3,5,8-tetrahydroxyxanthone

Crystal data

C23H24O6	Z = 2
Mr = 396.42	F(000) = 420
Triclinic, P1	Dx = 1.364 Mg m^−3
Hall symbol: -P 1	Melting point = 489–491 K
a = 7.1217 (13) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.3672 (14) Å	Cell parameters from 6315 reflections
c = 18.959 (3) Å	θ = 1.1–25.0°
α = 98.319 (3)°	µ = 0.10 mm^−1
β = 92.196 (3)°	T = 293 K
γ = 100.566 (3)°	Plate, yellow
V = 965.4 (3) Å^3	0.38 × 0.18 × 0.07 mm

Data collection

Siemens SMART CCD area-detector diffractometer	3387 independent reflections
Radiation source: fine-focus sealed tube	2794 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
Detector resolution: 8.33 pixels mm^-1	θmax = 25.0°, θmin = 1.1°
ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −8→8
Tmin = 0.964, Tmax = 0.993	l = −22→22
9351 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.056	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.165	w = 1/[σ^2(Fo^2) + (0.0942P)^2 + 0.2431P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.006
3387 reflections	Δρmax = 0.58 e Å^−3
282 parameters	Δρmin = −0.41 e Å^−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.043 (5)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.0912 (2)	0.3399 (2)	0.16537 (8)	0.0449 (4)
O2	0.2563 (3)	0.9937 (2)	0.21850 (9)	0.0632 (5)
O3	0.4152 (2)	0.76206 (19)	−0.15007 (8)	0.0461 (4)
O4	0.2087 (2)	0.03975 (18)	−0.09153 (9)	0.0495 (4)
O5	0.1337 (2)	0.18498 (17)	0.03554 (7)	0.0450 (4)
O6	0.30560 (18)	0.70809 (16)	−0.01711 (7)	0.0362 (4)
C1	0.1511 (2)	0.5063 (3)	0.14320 (10)	0.0349 (4)
C2	0.1673 (3)	0.6663 (3)	0.19294 (10)	0.0372 (5)
C3	0.2332 (3)	0.8372 (3)	0.16903 (10)	0.0404 (5)
C4	0.2751 (3)	0.8497 (3)	0.09894 (10)	0.0387 (5)
H4A	0.3133	0.9655	0.0845	0.046*
C4A	0.2592 (2)	0.6885 (2)	0.05136 (10)	0.0326 (4)
C5	0.3591 (3)	0.5848 (3)	−0.13391 (10)	0.0354 (4)
C6	0.3639 (3)	0.4325 (3)	−0.18479 (11)	0.0404 (5)
H6A	0.4020	0.4517	−0.2299	0.049*
C7	0.3136 (3)	0.2515 (3)	−0.17059 (11)	0.0424 (5)
H7A	0.3184	0.1512	−0.2060	0.051*
C8	0.2565 (3)	0.2194 (3)	−0.10433 (10)	0.0368 (5)
C8A	0.2505 (2)	0.3710 (2)	−0.05046 (10)	0.0336 (4)
C9	0.1906 (2)	0.3461 (2)	0.02009 (10)	0.0334 (4)
C9A	0.1981 (2)	0.5116 (2)	0.07129 (10)	0.0326 (4)
C10A	0.3039 (2)	0.5531 (2)	−0.06649 (10)	0.0320 (4)
C1'	0.1221 (3)	0.6548 (3)	0.26971 (11)	0.0444 (5)
H1'A	0.1056	0.7766	0.2929	0.053*
H1'B	0.0024	0.5678	0.2705	0.053*
C2'	0.2767 (3)	0.5924 (3)	0.31081 (10)	0.0440 (5)
H2'A	0.2901	0.4690	0.2979	0.053*
C3'	0.3965 (3)	0.6933 (3)	0.36348 (11)	0.0497 (6)
C4'	0.5571 (4)	0.6220 (4)	0.39791 (13)	0.0637 (7)
H4'A	0.6770	0.6902	0.3845	0.076*
H4'B	0.5541	0.6537	0.4493	0.076*
C5'	0.5606 (4)	0.4193 (4)	0.38147 (14)	0.0654 (7)
H5'A	0.5712	0.3862	0.3306	0.078*
H5'B	0.4408	0.3484	0.3937	0.078*
C6'	0.7249 (4)	0.3653 (4)	0.42161 (14)	0.0652 (7)
H6'A	0.7436	0.4144	0.4699	0.078*
C7'	0.8453 (4)	0.2579 (3)	0.39731 (14)	0.0606 (6)
C8'	0.8444 (5)	0.1701 (5)	0.32151 (17)	0.0929 (10)
H8'A	0.7418	0.2010	0.2941	0.139*
H8'B	0.8266	0.0369	0.3189	0.139*
H8'C	0.9641	0.2158	0.3026	0.139*
C9'	0.9895 (5)	0.2072 (5)	0.4465 (2)	0.0982 (11)
H9'A	0.9841	0.2720	0.4939	0.147*
H9'B	1.1152	0.2422	0.4303	0.147*
H9'C	0.9618	0.0749	0.4469	0.147*
C10'	0.3898 (5)	0.8926 (4)	0.39310 (16)	0.0819 (9)
H10A	0.3104	0.9413	0.3614	0.123*
H10B	0.5169	0.9662	0.3977	0.123*
H10C	0.3378	0.8974	0.4392	0.123*
H1O1	0.089 (4)	0.257 (4)	0.1273 (15)	0.071 (8)*
H1O3	0.353 (4)	0.833 (4)	−0.1256 (15)	0.070 (8)*
H1O2	0.297 (5)	1.078 (5)	0.2021 (18)	0.094 (12)*
H1O4	0.182 (5)	0.053 (4)	−0.0459 (17)	0.093 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0562 (9)	0.0354 (8)	0.0446 (8)	0.0050 (6)	0.0075 (7)	0.0152 (7)
O2	0.1052 (15)	0.0363 (9)	0.0461 (9)	0.0131 (9)	0.0021 (9)	0.0015 (7)
O3	0.0572 (9)	0.0346 (8)	0.0494 (9)	0.0077 (7)	0.0141 (7)	0.0147 (6)
O4	0.0681 (10)	0.0264 (7)	0.0550 (10)	0.0096 (6)	0.0131 (8)	0.0062 (6)
O5	0.0587 (9)	0.0274 (7)	0.0497 (8)	0.0049 (6)	0.0058 (7)	0.0123 (6)
O6	0.0450 (8)	0.0263 (7)	0.0381 (7)	0.0055 (5)	0.0034 (6)	0.0089 (5)
C1	0.0296 (9)	0.0352 (10)	0.0428 (11)	0.0082 (8)	0.0005 (8)	0.0140 (8)
C2	0.0332 (10)	0.0405 (11)	0.0403 (11)	0.0120 (8)	−0.0009 (8)	0.0092 (8)
C3	0.0469 (11)	0.0327 (10)	0.0420 (11)	0.0121 (8)	−0.0043 (9)	0.0029 (8)
C4	0.0448 (11)	0.0281 (10)	0.0437 (11)	0.0064 (8)	−0.0037 (9)	0.0091 (8)
C4A	0.0295 (9)	0.0315 (10)	0.0387 (10)	0.0073 (7)	−0.0018 (7)	0.0110 (8)
C5	0.0299 (9)	0.0344 (10)	0.0438 (11)	0.0061 (7)	0.0012 (8)	0.0125 (8)
C6	0.0397 (10)	0.0432 (11)	0.0407 (11)	0.0109 (8)	0.0063 (8)	0.0091 (9)
C7	0.0458 (11)	0.0367 (11)	0.0446 (11)	0.0120 (9)	0.0030 (9)	0.0010 (9)
C8	0.0354 (10)	0.0288 (9)	0.0468 (11)	0.0082 (7)	0.0007 (8)	0.0058 (8)
C8A	0.0285 (9)	0.0308 (10)	0.0434 (11)	0.0084 (7)	0.0001 (8)	0.0093 (8)
C9	0.0303 (9)	0.0278 (9)	0.0438 (10)	0.0067 (7)	−0.0016 (8)	0.0104 (8)
C9A	0.0283 (9)	0.0309 (10)	0.0399 (10)	0.0066 (7)	−0.0022 (7)	0.0096 (8)
C10A	0.0287 (9)	0.0280 (9)	0.0400 (10)	0.0074 (7)	−0.0008 (8)	0.0060 (8)
C1'	0.0453 (11)	0.0473 (12)	0.0434 (11)	0.0141 (9)	0.0050 (9)	0.0089 (9)
C2'	0.0520 (12)	0.0460 (11)	0.0388 (10)	0.0174 (9)	0.0070 (9)	0.0110 (9)
C3'	0.0521 (13)	0.0599 (14)	0.0396 (11)	0.0147 (10)	0.0048 (10)	0.0101 (10)
C4'	0.0672 (16)	0.0718 (17)	0.0532 (14)	0.0202 (13)	−0.0058 (12)	0.0073 (12)
C5'	0.0698 (16)	0.0673 (16)	0.0603 (15)	0.0144 (13)	−0.0092 (12)	0.0156 (12)
C6'	0.0756 (17)	0.0693 (16)	0.0543 (14)	0.0222 (14)	−0.0068 (12)	0.0134 (12)
C7'	0.0600 (14)	0.0536 (14)	0.0711 (16)	0.0135 (11)	0.0009 (12)	0.0167 (12)
C8'	0.114 (3)	0.093 (2)	0.081 (2)	0.040 (2)	0.0210 (19)	0.0140 (18)
C9'	0.077 (2)	0.102 (2)	0.123 (3)	0.0361 (18)	−0.020 (2)	0.024 (2)
C10'	0.092 (2)	0.0667 (18)	0.0808 (19)	0.0190 (15)	−0.0177 (16)	−0.0083 (15)

Geometric parameters (Å, º)

O1—C1	1.354 (2)	C9—C9A	1.435 (3)
O1—H1O1	0.87 (3)	C1'—C2'	1.501 (3)
O2—C3	1.357 (2)	C1'—H1'A	0.97
O2—H1O2	0.75 (3)	C1'—H1'B	0.97
O3—C5	1.375 (2)	C2'—C3'	1.328 (3)
O3—H1O3	0.85 (3)	C2'—H2'A	0.93
O4—C8	1.364 (2)	C3'—C10'	1.504 (4)
O4—H1O4	0.89 (3)	C3'—C4'	1.508 (3)
O5—C9	1.262 (2)	C4'—C5'	1.486 (4)
O6—C10A	1.366 (2)	C4'—H4'A	0.97
O6—C4A	1.373 (2)	C4'—H4'B	0.97
C1—C2	1.383 (3)	C5'—C6'	1.515 (3)
C1—C9A	1.421 (3)	C5'—H5'A	0.97
C2—C3	1.405 (3)	C5'—H5'B	0.97
C2—C1'	1.514 (3)	C6'—C7'	1.321 (3)
C3—C4	1.385 (3)	C6'—H6'A	0.93
C4—C4A	1.368 (3)	C7'—C8'	1.487 (4)
C4—H4A	0.93	C7'—C9'	1.494 (4)
C4A—C9A	1.406 (2)	C8'—H8'A	0.96
C5—C6	1.377 (3)	C8'—H8'B	0.96
C5—C10A	1.391 (3)	C8'—H8'C	0.96
C6—C7	1.384 (3)	C9'—H9'A	0.96
C6—H6A	0.93	C9'—H9'B	0.96
C7—C8	1.374 (3)	C9'—H9'C	0.96
C7—H7A	0.93	C10'—H10A	0.96
C8—C8A	1.408 (3)	C10'—H10B	0.96
C8A—C10A	1.406 (2)	C10'—H10C	0.96
C8A—C9	1.446 (3)
C1—O1—H1O1	104.5 (18)	C2—C1'—H1'A	109.1
C3—O2—H1O2	110 (3)	C2'—C1'—H1'B	109.1
C5—O3—H1O3	107.9 (18)	C2—C1'—H1'B	109.1
C8—O4—H1O4	103 (2)	H1'A—C1'—H1'B	107.9
C10A—O6—C4A	119.81 (14)	C3'—C2'—C1'	127.4 (2)
O1—C1—C2	117.72 (17)	C3'—C2'—H2'A	116.3
O1—C1—C9A	119.85 (17)	C1'—C2'—H2'A	116.3
C2—C1—C9A	122.43 (17)	C2'—C3'—C10'	123.4 (2)
C1—C2—C3	116.69 (17)	C2'—C3'—C4'	123.5 (2)
C1—C2—C1'	120.91 (18)	C10'—C3'—C4'	113.1 (2)
C3—C2—C1'	122.36 (18)	C5'—C4'—C3'	118.1 (2)
O2—C3—C4	120.34 (18)	C5'—C4'—H4'A	107.8
O2—C3—C2	116.70 (18)	C3'—C4'—H4'A	107.8
C4—C3—C2	122.96 (18)	C5'—C4'—H4'B	107.8
C4A—C4—C3	118.71 (17)	C3'—C4'—H4'B	107.8
C4A—C4—H4A	120.6	H4'A—C4'—H4'B	107.1
C3—C4—H4A	120.6	C4'—C5'—C6'	112.7 (2)
C4—C4A—O6	116.52 (16)	C4'—C5'—H5'A	109.1
C4—C4A—C9A	121.90 (17)	C6'—C5'—H5'A	109.1
O6—C4A—C9A	121.58 (16)	C4'—C5'—H5'B	109.1
O3—C5—C6	119.58 (17)	C6'—C5'—H5'B	109.1
O3—C5—C10A	122.19 (17)	H5'A—C5'—H5'B	107.8
C6—C5—C10A	118.19 (17)	C7'—C6'—C5'	128.8 (2)
C5—C6—C7	121.78 (18)	C7'—C6'—H6'A	115.6
C5—C6—H6A	119.1	C5'—C6'—H6'A	115.6
C7—C6—H6A	119.1	C6'—C7'—C8'	124.3 (2)
C8—C7—C6	120.21 (18)	C6'—C7'—C9'	121.2 (3)
C8—C7—H7A	119.9	C8'—C7'—C9'	114.4 (3)
C6—C7—H7A	119.9	C7'—C8'—H8'A	109.5
O4—C8—C7	119.10 (17)	C7'—C8'—H8'B	109.5
O4—C8—C8A	120.90 (17)	H8'A—C8'—H8'B	109.5
C7—C8—C8A	120.00 (17)	C7'—C8'—H8'C	109.5
C10A—C8A—C8	118.34 (17)	H8'A—C8'—H8'C	109.5
C10A—C8A—C9	119.11 (17)	H8'B—C8'—H8'C	109.5
C8—C8A—C9	122.55 (16)	C7'—C9'—H9'A	109.5
O5—C9—C9A	121.73 (17)	C7'—C9'—H9'B	109.5
O5—C9—C8A	120.95 (17)	H9'A—C9'—H9'B	109.5
C9A—C9—C8A	117.31 (16)	C7'—C9'—H9'C	109.5
C4A—C9A—C1	117.26 (17)	H9'A—C9'—H9'C	109.5
C4A—C9A—C9	119.80 (17)	H9'B—C9'—H9'C	109.5
C1—C9A—C9	122.91 (16)	C3'—C10'—H10A	109.5
O6—C10A—C5	116.28 (15)	C3'—C10'—H10B	109.5
O6—C10A—C8A	122.25 (17)	H10A—C10'—H10B	109.5
C5—C10A—C8A	121.47 (17)	C3'—C10'—H10C	109.5
C2'—C1'—C2	112.35 (16)	H10A—C10'—H10C	109.5
C2'—C1'—H1'A	109.1	H10B—C10'—H10C	109.5
O1—C1—C2—C3	178.80 (16)	O6—C4A—C9A—C9	2.5 (3)
C9A—C1—C2—C3	0.0 (3)	O1—C1—C9A—C4A	179.92 (15)
O1—C1—C2—C1'	0.9 (3)	C2—C1—C9A—C4A	−1.3 (3)
C9A—C1—C2—C1'	−177.95 (16)	O1—C1—C9A—C9	−1.8 (3)
C1—C2—C3—O2	−177.49 (17)	C2—C1—C9A—C9	176.94 (16)
C1'—C2—C3—O2	0.4 (3)	O5—C9—C9A—C4A	−178.86 (16)
C1—C2—C3—C4	2.1 (3)	C8A—C9—C9A—C4A	1.0 (2)
C1'—C2—C3—C4	179.99 (18)	O5—C9—C9A—C1	2.9 (3)
O2—C3—C4—C4A	176.81 (18)	C8A—C9—C9A—C1	−177.23 (15)
C2—C3—C4—C4A	−2.7 (3)	C4A—O6—C10A—C5	−177.83 (14)
C3—C4—C4A—O6	−178.84 (16)	C4A—O6—C10A—C8A	1.9 (3)
C3—C4—C4A—C9A	1.3 (3)	O3—C5—C10A—O6	0.9 (3)
C10A—O6—C4A—C4	176.20 (15)	C6—C5—C10A—O6	178.45 (15)
C10A—O6—C4A—C9A	−3.9 (2)	O3—C5—C10A—C8A	−178.76 (16)
O3—C5—C6—C7	178.34 (17)	C6—C5—C10A—C8A	−1.2 (3)
C10A—C5—C6—C7	0.8 (3)	C8—C8A—C10A—O6	−178.79 (15)
C5—C6—C7—C8	0.1 (3)	C9—C8A—C10A—O6	1.6 (3)
C6—C7—C8—O4	−179.63 (17)	C8—C8A—C10A—C5	0.9 (3)
C6—C7—C8—C8A	−0.5 (3)	C9—C8A—C10A—C5	−178.73 (15)
O4—C8—C8A—C10A	179.14 (16)	C1—C2—C1'—C2'	75.0 (2)
C7—C8—C8A—C10A	0.0 (3)	C3—C2—C1'—C2'	−102.9 (2)
O4—C8—C8A—C9	−1.3 (3)	C2—C1'—C2'—C3'	111.0 (2)
C7—C8—C8A—C9	179.59 (17)	C1'—C2'—C3'—C10'	2.6 (4)
C10A—C8A—C9—O5	176.91 (16)	C1'—C2'—C3'—C4'	−175.3 (2)
C8—C8A—C9—O5	−2.7 (3)	C2'—C3'—C4'—C5'	−11.4 (4)
C10A—C8A—C9—C9A	−2.9 (2)	C10'—C3'—C4'—C5'	170.6 (3)
C8—C8A—C9—C9A	177.49 (16)	C3'—C4'—C5'—C6'	−177.9 (2)
C4—C4A—C9A—C1	0.6 (3)	C4'—C5'—C6'—C7'	−134.3 (3)
O6—C4A—C9A—C1	−179.23 (15)	C5'—C6'—C7'—C8'	1.9 (5)
C4—C4A—C9A—C9	−177.66 (16)	C5'—C6'—C7'—C9'	−174.9 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O5	0.87 (3)	1.80 (3)	2.612 (2)	153 (3)
O2—H1O2···O3^i	0.75 (4)	2.48 (4)	3.124 (2)	144 (3)
O3—H1O3···O4^ii	0.85 (3)	2.03 (3)	2.855 (2)	164 (3)
O3—H1O3···O6	0.85 (3)	2.38 (3)	2.729 (2)	105 (2)
O4—H1O4···O5	0.89 (3)	1.78 (3)	2.607 (2)	153 (3)
C1′—H1′A···O2	0.97	2.42	2.826 (3)	105
C4—H4A···O5^ii	0.93	2.49	3.200 (3)	133

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