Caloxanthone C: a pyran-oxanthone from the stem bark of Calophyllum soulattri.

THE TITLE COMPOUND [SYSTEMATIC NAME: 5,10-di-hy-droxy-2,2-di-methyl-12-(2-methyl-but-3-en-2-yl)-pyrano[3,2-b]xanthen-6(2H)-one], C(23)H(22)O(5), isolated from the stem bark of Calophyllum soulattri, consists of four six-membered rings and a 2-methyl-but-3-en-2-yl side chain. The tricyclic xanthone ring system is almost planar [maximum deviation = 0.093 (2) Å], whereas the pyran-oid ring is in a distorted boat conformation. The 2-methyl-but-3-en-2-yl side chain is in a synperiplanar conformation. There are two intra-molecular O-H⋯O hydrogen bonds. In the crystal, mol-ecules are linked by C-H⋯O inter-actions, forming a zigzag chain propagating in [010].

Related literature

For related structures, see: Ee et al. (2010 ▶); Fun et al. (2006 ▶); Doriguetto et al. (2001 ▶); Boonnak et al. (2007 ▶); Ndjakou et al. (2007 ▶). For the biological activity of Calophyllum species, see: Dharmaratne et al. (1999 ▶, 2009 ▶); Zou et al. (2005 ▶); Ito et al. (1999 ▶, 2002 ▶); Ee et al. (2004 ▶). For standard bond lengths, see Allen et al. (1987 ▶).

Experimental

Crystal data

C23H22O5

M = 378.42

Monoclinic,

a = 6.7013 (3) Å

b = 15.8951 (7) Å

c = 17.3891 (7) Å

β = 93.181 (4)°

V = 1849.39 (14) Å3

Z = 4

Cu Kα radiation

μ = 0.78 mm−1

T = 150 K

0.34 × 0.15 × 0.07 mm

Data collection

Oxford Diffraction Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006 ▶) T min = 0.890, T max = 0.947

10133 measured reflections

3503 independent reflections

3048 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.170

S = 1.00

3488 reflections

254 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.34 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: CRYSTALS.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536811036294/su2302sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036294/su2302Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811036294/su2302Isup3.cml

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

C23H22O5	F(000) = 800
Mr = 378.42	Dx = 1.359 Mg m−3
Monoclinic, P21/n	Melting point: 189 K
Hall symbol: -P 2yn	Cu Kα radiation, λ = 1.54184 Å
a = 6.7013 (3) Å	Cell parameters from 4840 reflections
b = 15.8951 (7) Å	θ = 71–4°
c = 17.3891 (7) Å	µ = 0.78 mm−1
β = 93.181 (4)°	T = 150 K
V = 1849.39 (14) Å3	Plate, yellow
Z = 4	0.34 × 0.15 × 0.07 mm

Oxford Diffraction Gemini diffractometer	3503 independent reflections
Radiation source: sealed x-ray tube	3048 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω/2θ scans	θmax = 70.9°, θmin = 3.8°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006)	h = −8→8
Tmin = 0.890, Tmax = 0.947	k = 0→19
10133 measured reflections	l = 0→21

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.056	Method = Modified Sheldrick w = 1/[σ2(F2) + ( 0.08P)2 + 2.61P] , where P = (max(Fo2,0) + 2Fc2)/3
wR(F2) = 0.170	(Δ/σ)max = 0.0002304
S = 1.00	Δρmax = 0.34 e Å−3
3488 reflections	Δρmin = −0.34 e Å−3
254 parameters	Extinction correction: Larson (1970), Equation 22
0 restraints	Extinction coefficient: 27 (7)
Primary atom site location: structure-invariant direct methods

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. For this compound, 10133 numbers of reflections were collected and measured during the refinement. Symmetry related reflections were measured more than once and after merging the symmetry equivalent reflections there were only 3503 reflection left. 15 more reflections were filtered, as σ cutoff was set as -3 and (sinθ/x)set to>0.01 (to eliminate reflection measured near the vicinity of beam stop) therefore numbers of reflection reduced to 3488.

	x	y	z	Uiso*/Ueq
O1	0.2643 (2)	0.41026 (9)	0.57160 (8)	0.0229 (4)
O5	0.2129 (3)	0.53596 (10)	0.36618 (9)	0.0307 (5)
O10	0.2854 (2)	0.14802 (10)	0.44806 (9)	0.0278 (5)
O16	0.2066 (3)	0.39365 (10)	0.29598 (8)	0.0303 (5)
O28	0.3025 (3)	0.48977 (10)	0.70816 (9)	0.0353 (6)
C2	0.2663 (3)	0.49629 (13)	0.56988 (12)	0.0210 (6)
C3	0.2503 (3)	0.54285 (13)	0.50222 (12)	0.0218 (6)
C4	0.2296 (3)	0.49750 (14)	0.42909 (12)	0.0230 (6)
C6	0.2301 (3)	0.40664 (13)	0.43370 (12)	0.0203 (6)
C7	0.2456 (3)	0.36432 (13)	0.50527 (11)	0.0197 (6)
C8	0.2438 (3)	0.27680 (13)	0.51359 (12)	0.0208 (6)
C9	0.2496 (3)	0.23212 (13)	0.44407 (12)	0.0214 (6)
C11	0.2127 (4)	0.09367 (15)	0.38384 (13)	0.0309 (7)
C12	0.2517 (4)	0.13517 (16)	0.30843 (13)	0.0317 (7)
C13	0.2589 (3)	0.21808 (15)	0.30307 (13)	0.0272 (7)
C14	0.2370 (3)	0.27046 (14)	0.37081 (12)	0.0226 (6)
C15	0.2218 (3)	0.35722 (14)	0.36604 (12)	0.0230 (6)
C17	0.3296 (5)	0.01284 (17)	0.39606 (16)	0.0449 (9)
C18	−0.0109 (4)	0.07989 (16)	0.39128 (14)	0.0362 (8)
C19	0.2517 (3)	0.23222 (13)	0.59319 (12)	0.0247 (6)
C20	0.1635 (3)	0.28569 (13)	0.65545 (12)	0.0242 (6)
C21	0.2403 (4)	0.29604 (14)	0.72643 (13)	0.0275 (7)
C22	0.4673 (4)	0.20684 (17)	0.61492 (13)	0.0380 (8)
C23	0.1135 (5)	0.15364 (17)	0.59174 (15)	0.0455 (9)
C24	0.2559 (3)	0.63098 (14)	0.50689 (13)	0.0261 (7)
C25	0.2754 (3)	0.66952 (14)	0.57769 (15)	0.0289 (7)
C26	0.2914 (3)	0.62217 (15)	0.64509 (14)	0.0285 (7)
C27	0.2857 (3)	0.53529 (14)	0.64196 (13)	0.0253 (6)
H12	0.26450	0.10080	0.26490	0.0384*
H13	0.28030	0.24340	0.25580	0.0331*
H16	0.19700	0.44460	0.30570	0.0463*
H171	0.31860	−0.00790	0.44700	0.0664*
H172	0.28140	−0.02920	0.35990	0.0668*
H173	0.46950	0.02260	0.38840	0.0665*
H181	−0.03090	0.05220	0.43970	0.0529*
H182	−0.07820	0.13340	0.38910	0.0531*
H183	−0.06030	0.04520	0.35010	0.0534*
H20	0.03660	0.31080	0.64190	0.0285*
H211	0.36950	0.27610	0.74130	0.0327*
H212	0.16730	0.32320	0.76280	0.0333*
H221	0.55190	0.25610	0.62300	0.0565*
H222	0.51750	0.17280	0.57450	0.0567*
H223	0.47390	0.17320	0.66120	0.0565*
H231	0.09990	0.13450	0.64360	0.0671*
H232	−0.01540	0.17000	0.56910	0.0678*
H233	0.16600	0.10830	0.56210	0.0677*
H24	0.24530	0.66350	0.46210	0.0304*
H25	0.27720	0.72990	0.58170	0.0349*
H26	0.30550	0.64830	0.69310	0.0342*
H28	0.29350	0.44000	0.69800	0.0529*

	U11	U22	U33	U12	U13	U23
O1	0.0319 (8)	0.0176 (8)	0.0189 (7)	−0.0017 (6)	−0.0004 (6)	−0.0005 (6)
O5	0.0401 (10)	0.0266 (9)	0.0250 (8)	0.0005 (7)	−0.0005 (7)	0.0077 (6)
O10	0.0396 (9)	0.0191 (8)	0.0238 (8)	0.0034 (7)	−0.0053 (7)	−0.0037 (6)
O16	0.0421 (10)	0.0300 (9)	0.0184 (8)	0.0007 (7)	−0.0007 (7)	0.0032 (6)
O28	0.0587 (12)	0.0246 (9)	0.0222 (8)	−0.0023 (8)	−0.0006 (7)	−0.0024 (6)
C2	0.0197 (10)	0.0174 (10)	0.0260 (11)	−0.0002 (8)	0.0012 (8)	0.0000 (8)
C3	0.0156 (10)	0.0217 (11)	0.0279 (11)	−0.0009 (8)	0.0006 (8)	0.0012 (8)
C4	0.0198 (10)	0.0244 (11)	0.0247 (11)	0.0003 (8)	0.0011 (8)	0.0041 (9)
C6	0.0163 (10)	0.0230 (11)	0.0214 (10)	−0.0002 (8)	−0.0003 (8)	0.0011 (8)
C7	0.0189 (10)	0.0212 (11)	0.0189 (10)	−0.0009 (8)	0.0001 (8)	−0.0015 (8)
C8	0.0215 (10)	0.0205 (11)	0.0200 (10)	−0.0011 (8)	−0.0019 (8)	0.0004 (8)
C9	0.0203 (10)	0.0197 (11)	0.0239 (11)	−0.0005 (8)	−0.0021 (8)	−0.0006 (8)
C11	0.0449 (14)	0.0216 (11)	0.0254 (11)	0.0011 (10)	−0.0049 (10)	−0.0080 (9)
C12	0.0371 (13)	0.0327 (13)	0.0250 (11)	0.0040 (10)	0.0001 (9)	−0.0102 (10)
C13	0.0272 (11)	0.0340 (13)	0.0203 (10)	0.0016 (9)	−0.0002 (8)	−0.0033 (9)
C14	0.0196 (10)	0.0265 (11)	0.0212 (10)	0.0008 (8)	−0.0019 (8)	−0.0026 (9)
C15	0.0211 (10)	0.0285 (12)	0.0191 (10)	0.0005 (8)	−0.0006 (8)	0.0032 (8)
C17	0.0671 (19)	0.0267 (13)	0.0397 (15)	0.0126 (13)	−0.0079 (13)	−0.0097 (11)
C18	0.0505 (16)	0.0276 (12)	0.0295 (12)	−0.0087 (11)	−0.0068 (11)	−0.0020 (10)
C19	0.0356 (12)	0.0187 (10)	0.0196 (10)	−0.0026 (9)	−0.0012 (9)	0.0013 (8)
C20	0.0268 (11)	0.0203 (10)	0.0255 (11)	−0.0029 (9)	0.0024 (8)	0.0049 (8)
C21	0.0334 (12)	0.0270 (11)	0.0225 (11)	−0.0013 (9)	0.0052 (9)	0.0015 (9)
C22	0.0502 (16)	0.0403 (14)	0.0233 (12)	0.0203 (12)	0.0004 (11)	0.0061 (10)
C23	0.079 (2)	0.0295 (14)	0.0283 (13)	−0.0245 (14)	0.0062 (13)	0.0016 (10)
C24	0.0226 (11)	0.0215 (11)	0.0339 (12)	0.0000 (8)	−0.0002 (9)	0.0055 (9)
C25	0.0225 (11)	0.0189 (11)	0.0452 (14)	−0.0012 (8)	0.0020 (10)	−0.0024 (10)
C26	0.0276 (12)	0.0253 (12)	0.0323 (12)	0.0001 (9)	−0.0001 (9)	−0.0085 (9)
C27	0.0248 (11)	0.0241 (11)	0.0270 (11)	−0.0021 (9)	0.0011 (9)	−0.0019 (9)

O1—C2	1.368 (3)	C19—C20	1.522 (3)
O1—C7	1.365 (2)	C19—C22	1.527 (3)
O5—C4	1.253 (3)	C20—C21	1.321 (3)
O10—C9	1.359 (3)	C24—C25	1.375 (3)
O10—C11	1.473 (3)	C25—C26	1.392 (3)
O16—C15	1.348 (3)	C26—C27	1.383 (3)
O28—C27	1.359 (3)	C12—H12	0.9400
O16—H16	0.8300	C13—H13	0.9300
O28—H28	0.8100	C17—H171	0.9500
C2—C27	1.398 (3)	C17—H172	0.9600
C2—C3	1.389 (3)	C17—H173	0.9700
C3—C24	1.404 (3)	C18—H181	0.9700
C3—C4	1.462 (3)	C18—H182	0.9600
C4—C6	1.446 (3)	C18—H183	0.9500
C6—C7	1.413 (3)	C20—H20	0.9600
C6—C15	1.413 (3)	C21—H211	0.9400
C7—C8	1.399 (3)	C21—H212	0.9300
C8—C9	1.405 (3)	C22—H221	0.9700
C8—C19	1.553 (3)	C22—H222	0.9600
C9—C14	1.411 (3)	C22—H223	0.9700
C11—C17	1.514 (4)	C23—H231	0.9600
C11—C18	1.527 (4)	C23—H232	0.9600
C11—C12	1.504 (3)	C23—H233	0.9600
C12—C13	1.322 (3)	C24—H24	0.9300
C13—C14	1.457 (3)	C25—H25	0.9600
C14—C15	1.385 (3)	C26—H26	0.9300
C19—C23	1.554 (4)
C2—O1—C7	121.12 (16)	C3—C24—C25	119.8 (2)
C9—O10—C11	119.21 (17)	C24—C25—C26	120.8 (2)
C15—O16—H16	104.00	C25—C26—C27	120.4 (2)
C27—O28—H28	109.00	C2—C27—C26	118.6 (2)
O1—C2—C27	115.10 (18)	O28—C27—C2	121.51 (19)
O1—C2—C3	123.42 (18)	O28—C27—C26	119.9 (2)
C3—C2—C27	121.48 (19)	C11—C12—H12	118.00
C4—C3—C24	122.92 (19)	C13—C12—H12	121.00
C2—C3—C24	118.83 (19)	C12—C13—H13	120.00
C2—C3—C4	118.25 (19)	C14—C13—H13	120.00
O5—C4—C3	121.2 (2)	C11—C17—H171	111.00
O5—C4—C6	122.38 (19)	C11—C17—H172	110.00
C3—C4—C6	116.38 (18)	C11—C17—H173	110.00
C4—C6—C7	121.59 (19)	H171—C17—H172	109.00
C7—C6—C15	117.78 (19)	H171—C17—H173	108.00
C4—C6—C15	120.60 (19)	H172—C17—H173	108.00
O1—C7—C8	116.46 (17)	C11—C18—H181	109.00
O1—C7—C6	119.23 (18)	C11—C18—H182	109.00
C6—C7—C8	124.32 (19)	C11—C18—H183	109.00
C7—C8—C19	123.08 (18)	H181—C18—H182	110.00
C7—C8—C9	114.40 (18)	H181—C18—H183	109.00
C9—C8—C19	122.35 (18)	H182—C18—H183	110.00
C8—C9—C14	123.77 (19)	C19—C20—H20	116.00
O10—C9—C8	117.82 (18)	C21—C20—H20	118.00
O10—C9—C14	118.20 (18)	C20—C21—H211	121.00
O10—C11—C17	104.15 (19)	C20—C21—H212	120.00
O10—C11—C12	109.73 (19)	H211—C21—H212	119.00
C12—C11—C18	110.8 (2)	C19—C22—H221	111.00
O10—C11—C18	107.74 (18)	C19—C22—H222	109.00
C12—C11—C17	112.4 (2)	C19—C22—H223	111.00
C17—C11—C18	111.7 (2)	H221—C22—H222	109.00
C11—C12—C13	120.5 (2)	H221—C22—H223	109.00
C12—C13—C14	120.5 (2)	H222—C22—H223	107.00
C9—C14—C13	118.7 (2)	C19—C23—H231	109.00
C9—C14—C15	119.00 (19)	C19—C23—H232	108.00
C13—C14—C15	122.1 (2)	C19—C23—H233	112.00
O16—C15—C6	120.75 (19)	H231—C23—H232	110.00
C6—C15—C14	120.28 (19)	H231—C23—H233	109.00
O16—C15—C14	118.92 (19)	H232—C23—H233	109.00
C8—C19—C22	109.03 (17)	C3—C24—H24	120.00
C8—C19—C23	111.18 (18)	C25—C24—H24	120.00
C20—C19—C23	101.88 (18)	C24—C25—H25	121.00
C22—C19—C23	110.3 (2)	C26—C25—H25	119.00
C20—C19—C22	111.78 (17)	C25—C26—H26	121.00
C8—C19—C20	112.58 (17)	C27—C26—H26	119.00
C19—C20—C21	126.0 (2)
C7—O1—C2—C3	−0.1 (3)	O1—C7—C8—C9	−172.41 (17)
C7—O1—C2—C27	179.82 (17)	O1—C7—C8—C19	3.0 (3)
C2—O1—C7—C6	0.6 (3)	C6—C7—C8—C9	7.4 (3)
C2—O1—C7—C8	−179.54 (17)	C6—C7—C8—C19	−177.21 (19)
C11—O10—C9—C8	154.62 (19)	C7—C8—C9—O10	168.09 (17)
C11—O10—C9—C14	−30.5 (3)	C7—C8—C9—C14	−6.5 (3)
C9—O10—C11—C12	42.9 (3)	C19—C8—C9—O10	−7.3 (3)
C9—O10—C11—C17	163.42 (19)	C19—C8—C9—C14	178.13 (19)
C9—O10—C11—C18	−77.9 (2)	C7—C8—C19—C20	27.6 (3)
O1—C2—C3—C4	0.2 (3)	C7—C8—C19—C22	−97.0 (2)
O1—C2—C3—C24	−179.41 (18)	C7—C8—C19—C23	141.2 (2)
C27—C2—C3—C4	−179.74 (19)	C9—C8—C19—C20	−157.36 (19)
C27—C2—C3—C24	0.6 (3)	C9—C8—C19—C22	78.0 (2)
O1—C2—C27—O28	0.4 (3)	C9—C8—C19—C23	−43.8 (3)
O1—C2—C27—C26	179.23 (18)	O10—C9—C14—C13	1.2 (3)
C3—C2—C27—O28	−179.6 (2)	O10—C9—C14—C15	−173.23 (18)
C3—C2—C27—C26	−0.8 (3)	C8—C9—C14—C13	175.72 (19)
C2—C3—C4—O5	179.4 (2)	C8—C9—C14—C15	1.3 (3)
C2—C3—C4—C6	−0.8 (3)	O10—C11—C12—C13	−28.3 (3)
C24—C3—C4—O5	−1.0 (3)	C17—C11—C12—C13	−143.7 (2)
C24—C3—C4—C6	178.85 (19)	C18—C11—C12—C13	90.6 (3)
C2—C3—C24—C25	−0.5 (3)	C11—C12—C13—C14	2.4 (4)
C4—C3—C24—C25	179.91 (19)	C12—C13—C14—C9	13.0 (3)
O5—C4—C6—C7	−178.9 (2)	C12—C13—C14—C15	−172.8 (2)
O5—C4—C6—C15	3.3 (3)	C9—C14—C15—O16	−178.96 (19)
C3—C4—C6—C7	1.3 (3)	C9—C14—C15—C6	3.5 (3)
C3—C4—C6—C15	−176.56 (18)	C13—C14—C15—O16	6.8 (3)
C4—C6—C7—O1	−1.2 (3)	C13—C14—C15—C6	−170.74 (19)
C4—C6—C7—C8	178.96 (19)	C8—C19—C20—C21	−136.6 (2)
C15—C6—C7—O1	176.65 (18)	C22—C19—C20—C21	−13.5 (3)
C15—C6—C7—C8	−3.2 (3)	C23—C19—C20—C21	104.3 (3)
C4—C6—C15—O16	−2.2 (3)	C3—C24—C25—C26	0.5 (3)
C4—C6—C15—C14	175.28 (19)	C24—C25—C26—C27	−0.7 (3)
C7—C6—C15—O16	179.87 (19)	C25—C26—C27—O28	179.67 (19)
C7—C6—C15—C14	−2.6 (3)	C25—C26—C27—C2	0.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O16—H16···O5	0.83	1.79	2.570 (2)	155
O28—H28···O1	0.81	2.25	2.690 (2)	115
C12—H12···O5i	0.94	2.51	3.441 (3)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O16—H16⋯O5	0.83	1.79	2.570 (2)	155
O28—H28⋯O1	0.81	2.25	2.690 (2)	115
C12—H12⋯O5i	0.94	2.51	3.441 (3)	168

Symmetry code: (i) .