Issue contents cross.png
Download PDF of article cross.png
Download CIF cross.png
3D view cross.png
Navigation cross.png
Highlighting cross.png
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation cross.png
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
Text
cross.png
share
Previous article cross.png
Next article cross.png
Previous article cross.png
Issue contents cross.png
Download PDF of article cross.png
Download CIF cross.png
3D view cross.png
Navigation cross.png
Highlighting cross.png
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation cross.png
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
Text
cross.png
share
Next article cross.png

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 8| Part 1| January 2023| x221198
https://doi.org/10.1107/S2414314622011981

5,8-Dihy­dr­oxy-2,2-di­methyl-12-(3-methyl­but-2-en­yl)pyrano[3,2-b]xanthen-6-one (brasixanthone B)

crossmark logo
Nurr Maria Ulfa Binti Seruji,a Mohd Mustaqim Rosli,b Vivien Yi Mian Jong,a* Thiruventhan Karunakaran,c,d Mas Atikah Lizazman,a Anita Marlinae,f and Yanti Yana Binti Halida

aCentre of Applied Science Studies, Universiti Teknologi MARA Sarawak, 94300 Kota Samarahan, Sarawak, Malaysia, bX-ray Crystallography Unit, School of Physics, University Sains Malaysia, 11800 USM, Penang, ., Malaysia, cCentre of Drug Research, Universiti Sains Malaysia, 11800 USM, Pulau Pinang, Malaysia, dSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, eResearch Centre for Chemistry, National Research and Innovation Agency, Indonesia, and fDepartment of Chemistry, Faculty of Science, University of Malaya, 50603, Malaysia
*Correspondence e-mail: vivien@uitm.edu.my

Edited by S. Parkin, University of Kentucky, USA (Received 12 October 2022; accepted 19 December 2022; online 6 January 2023)

The title compound (trivial name brasixanthone B), C23H22O5, isolated from Calophyllum gracilentum, is characterized by a xanthone skeleton of three fused six-membered rings plus an additional fused pyrano ring and one 3-methyl­but-2-enyl side chain. The core xanthone moiety is almost planar, with a maximum deviation 0.057 (4) Å from the mean plane. In the mol­ecule, an intra­molecular O—H⋯O hydrogen bond forms an S(6) ring motif. The crystal structure features inter­molecular O—H⋯O and C—H⋯O inter­actions.

CCDC reference: 2227328

Similar articles
3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Calophyllum, frequently referred as `bintangor' or `penaga' in Malay is a part of the Calophyllaceae family (Crane et al., 2005[Crane, S., Aurore, G., Joseph, H., Mouloungui, Z. & Bourgeois, P. (2005). Phytochemistry, 66, 1825-1831.]; Filho et al., 2009[Filho, V. C., Meyre-Silva, C. & Niero, R. (2009). Chem. Biodivers. B, 6, 313-327.]). 80 different species have been identified in Malaysia (Corner, 1952[Corner, E. J. H. (1952). Wayside Trees of Malaya, Vol. 1. Singapore: The Government Printing Office.]), but studies on only 45 of them have been reported so far (Wang et al., 2019[Wang, Z., Sun, F., Wang, J., Dong, J., Xie, S., Sun, M. & Sun, B. (2019). Historical Biology, 31, 1379-1393.]). The ethnobotanical uses of Calophyllum in traditional medicine has been utilising several Calophyllum species for many thousands of years. This genus is well known for its medicinal uses and has been traditionally used for the treatment of potentially chronic diseases such as peptic ulcers, malaria, tumors, infections, high blood pressure, rheumatic disorders, eye infections, hemorrhoids, inflammation, malaria, and certain venereal diseases (Dweck & Meadows, 2002[Dweck, A. & Meadows, T. (2002). Int. J. Cosmet. Sci. 24, 341-348.]; Thia­garajan et al., 2017[Thiagarajan, S., Yong, F.-L., Subramaniam, H., Jong, V. Y.-M., Lim, C.-K. & Say, Y.-H. (2017). Trop. J. Pharm. Res. 16, 563-572.]; Zamakshshari et al., 2019[Zamakshshari, N. H., Ee, G. C. L., Ismail, I. S., Ibrahim, Z. & Mah, S. H. (2019). Food Chem. Toxicol. 133, 110800.]; Gupta & Gupta, 2020[Gupta, S. & Gupta, P. (2020). Bioactive Nat. Prod. Drug Discov. 8, 215-242.]). For the biological activity of Calophyllum species, see: Guilet et al. (2001[Guilet, D., Hélesbeux, J.-J., Séraphin, D., Sévenet, T., Richomme, P. & Bruneton, J. (2001). J. Nat. Prod. 64, 563-568.]); Mah et al. (2012[Mah, S. H., Ee, G. C. L., Teh, S. S., Rahmani, M., Lim, Y. M. & Go, R. (2012). Molecules, 17, 8303-8311.];) Reyes-Chilpa et al. (2004[Reyes-Chilpa, R., Estrada-Muñiz, E., Ram\?írez Apan, T., Amekraz, B., Aumelas, A., Jankowski, C. K. & Vázquez-Torres, M. (2004). Life Sci. 75, 1635-1647.]); Aminudin et al. (2015[Aminudin, N. I., Ahmad, F., Taher, M. & Zulkifli, R. M. (2015). Nat. Prod. Commun. 10, 1585-1587.]); Lim et al. (2017[Lim, C.-K., Hemaroopini, S., Say, Y.-H. & Jong, V. Y.-M. (2017). Nat. Prod. Commun. 12, 1469-1471.], 2019[Lim, C. K., Ham, Y. P., Lim, L. Q. & Jong, V. Y. M. (2019). Phytochemistry Lett. 30, 99-102.]); Zamakshshari et al. (2019[Zamakshshari, N. H., Ee, G. C. L., Ismail, I. S., Ibrahim, Z. & Mah, S. H. (2019). Food Chem. Toxicol. 133, 110800.]); Karunakaran et al., 2022[Karunakaran, T., Firouz, N. S., Santhanam, R. & Jong, V. Y. M. (2022). Nat. Prod. Res. 36, 654-659.]) and Gupta & Gupta (2020[Gupta, S. & Gupta, P. (2020). Bioactive Nat. Prod. Drug Discov. 8, 215-242.]). Novel xanthones and coumarins are being identified from Calophyllum species on a regular basis (Aminudin et al., 2015[Aminudin, N. I., Ahmad, F., Taher, M. & Zulkifli, R. M. (2015). Nat. Prod. Commun. 10, 1585-1587.]; Li et al., 2016[Li, W., Guo, Y., Zhang, C., Wu, R., Yang, A. Y., Gaspar, J. & Kong, A.-N. T. (2016). Chem. Res. Toxicol. 29, 2071-2095.]). The X-ray crystallographic structure for the title compound, brasixanthone B, isolated from Calophyllum gracilentum is reported herein. Related structures have been reported by Ito et al. (2002[Ito, C., Itoigawa, M., Mishina, Y., Filho, V. C., Mukainaka, T., Tokuda, H., Nishino, H. & Furukawa, H. (2002). J. Nat. Prod. 65, 267-272.]) and Mah et al. (2012[Mah, S. H., Ee, G. C. L., Teh, S. S., Rahmani, M., Lim, Y. M. & Go, R. (2012). Molecules, 17, 8303-8311.]).

The orientation of the 3-methyl­but-2-enyl side chain attached to ring B can be defined by the torsion angles C14—C15—C19—C20 and C16—C15—C19—C20, which have values of −85.2 (5) and 94.2 (4)°, respectively, suggesting a synclinal conformation (Ee et al., 2010[Ee, G. C. L., Sim, W. C., Kwong, H. C., Mohamed Tahir, M. I. & Silong, S. (2010). Acta Cryst. E66, o3362-o3363.]). Ring A, a 3,6-di­hydro-2H-pyran, forms a screw-boat conformation (Cremer & Pople, 1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]), with puckering parameters Q = 0.352 (4) Å, θ = 65.4 (7)° and φ = 38.2 (7)°. The core xanthone moiety (rings B, C and D) is almost planar, with maximum deviation of 0.057 (4) Å from the mean plane for C16. The dihedral angles between xanthone rings are: 2.29 (19)° for B and C, 2.94 (19)° for B and D, and 0.75 (19)° between C and D. There are two methyl groups attached to atom C1 in ring A with C—C distances of 1.488 (6) and 1.483 (6) Å.

In the title compound (Fig. 1[link]), an intra­molecular hydrogen bond, O3—H1O3⋯O4, forms an S(6) ring motif. In the crystal, the mol­ecules are linked by inter­molecular hydrogen bonds O5—H1O5⋯O4, C11—H11A⋯O3 and C12—H12A⋯O5 (Table 1[link]), forming extended layers lying parallel to (101) (Fig. 2[link]). Inversion-related (1 − x, 1 − y, 2 − x) mol­ecules are stacked by π–π inter­actions with an inter­planar spacing of 3.319 (4) Å between corresponding xanthone rings.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O3—H1O3⋯O4 0.82 1.77 2.520 (3) 152
O5—H1O5⋯O4i 0.82 1.89 2.679 (4) 160
C11—H11A⋯O3ii 0.93 2.58 3.352 (5) 141
C12—H12A⋯O5iii 0.93 2.50 3.352 (5) 152
Symmetry codes: (i) [-x+1, -y, -z+2]; (ii) [x-{\script{3\over 2}}, -y-{\script{1\over 2}}, z-{\script{3\over 2}}]; (iii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].
[Figure 1]
Figure 1
The mol­ecular structure of brasixanthone B showing the atomic labeling. Displacement ellipsoids are drawn at the 30% probability level. The intra­molecular hydrogen bond is shown as a dashed line.
[Figure 2]
Figure 2
The crystal packing of brasixanthone B viewed along the b-axis direction. Hydrogen bonds are shown as dashed lines. Hydrogen atoms not involved in hydrogen bonds are omitted for clarity.

Synthesis and crystallization

The stem bark (1.2 kg) of calophyllum gracilentum was ground and extracted with n-hexane, chloro­form, ethyl acetate and methanol. Fractionation of the hexane extract by gravity column chromatography over (Merck Kieselgel No. 1.09385.1000) silica gel with elution of n-hexa­ne: ethyl acetate and ethyl acetate: methanol in a step-wise gradual increment in polarity. This produced 28 fractions, which were combined and pooled together as 10 sub-fractions based on the TLC profile. Fraction 5 was subjected to further isolation by column chromatography over Sephadex LH20 eluted with methanol and several more purification steps using radial chromatography over silica (Merck Kieselgel No. 1.07749.1000), eluting with an n-hexa­ne:ethyl acetate (8:2) mixture. Yellow needle-like crystals were obtained. The melting point was found to be 500–502 K (Ee et al., 2011[Ee, G. C. L., Mah, S. H., Teh, S. S., Rahmani, M., Go, R. & Taufiq-Yap, Y. H. (2011). Molecules, 16, 9721-9727.]).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C23H22O5
Mr 378.40
Crystal system, space group Monoclinic, P21/n
Temperature (K) 296
a, b, c (Å) 13.071 (3), 10.458 (3), 13.358 (3)
β (°) 90.576 (19)
V (Å3) 1825.9 (8)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.10
Crystal size (mm) 0.31 × 0.31 × 0.31
 
Data collection
Diffractometer Bruker APEX Duo CCD area detector
Absorption correction Multi-scan (SADABS; Bruker, 2012[Bruker (2012). APEX2, SAINT, and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.773, 0.944
No. of measured, independent and observed [I > 2σ(I)] reflections 39924, 2381, 1409
Rint 0.117
θmax (°) 22.5
(sin θ/λ)max (Å−1) 0.538
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.063, 0.198, 1.08
No. of reflections 2381
No. of parameters 257
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.27, −0.24
Computer programs: APEX2 and SAINT (Bruker, 2012[Bruker (2012). APEX2, SAINT, and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXT (Sheldrick, 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.]), SHELXL2014/7 (Sheldrick, 2015b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]), SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and PLATON (Spek, 2020[Spek, A. L. (2020). Acta Cryst. E76, 1-11.]).

Structural data

CCDC reference: 2227328

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314622011981/pk4037sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314622011981/pk4037Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314622011981/pk4037Isup3.cml

checkCIF report


Computing details top

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2020).

5,8-Dihydroxy-2,2-dimethyl-12-(3-methylbut-2-enyl)pyrano[3,2-b]xanthen-6-one top
Crystal data top
C23H22O5F(000) = 800
Mr = 378.40Dx = 1.377 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 13.071 (3) ÅCell parameters from 2238 reflections
b = 10.458 (3) Åθ = 2.2–26.0°
c = 13.358 (3) ŵ = 0.10 mm−1
β = 90.576 (19)°T = 296 K
V = 1825.9 (8) Å3Block, orange
Z = 40.31 × 0.31 × 0.31 mm
Data collection top
Bruker APEX Duo CCD area detector
diffractometer		1409 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.117
φ and ω scansθmax = 22.5°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)		h = −14→14
Tmin = 0.773, Tmax = 0.944k = −11→11
39924 measured reflectionsl = −14→14
2381 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.063H-atom parameters constrained
wR(F2) = 0.198 w = 1/[σ2(Fo2) + (0.1114P)2 + 0.0299P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
2381 reflectionsΔρmax = 0.27 e Å−3
257 parametersΔρmin = −0.24 e Å−3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. The O-bound H atoms were located in a difference map, but fixed during refinement, with distance set to 0.82 Å and Uiso(H) = 1.5Ueq(O). The remaining H atoms were place in calculated positions with d(C-H) = 0.93 Å for aromatic, 0.97 Å for CH2 and 0.96 Å for CH3 atoms. The Uiso(H) values were constrained to be 1.5Ueq of the carrier atom for methyl H atoms and 1.2Ueq for the remaining H atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.6393 (2)0.7811 (2)0.86169 (18)0.0705 (8)
O20.44525 (18)0.4259 (2)0.80181 (17)0.0591 (7)
O30.70808 (19)0.4135 (2)1.04401 (18)0.0706 (8)
H1O30.68830.33911.04240.106*
O40.60038 (19)0.2194 (2)1.00573 (19)0.0700 (8)
O50.3386 (2)−0.0672 (2)0.8438 (2)0.0850 (9)
H1O50.3681−0.10010.89180.127*
C10.7421 (3)0.8284 (4)0.8784 (3)0.0756 (12)
C20.7815 (3)0.7784 (4)0.9731 (3)0.0755 (12)
H2A0.82730.82721.01070.091*
C30.7539 (3)0.6671 (4)1.0056 (3)0.0694 (11)
H3A0.78410.63331.06320.083*
C40.6778 (3)0.5970 (4)0.9535 (3)0.0554 (10)
C50.6545 (3)0.4736 (4)0.9740 (3)0.0560 (10)
C60.5765 (3)0.4110 (3)0.9236 (3)0.0496 (9)
C70.5540 (3)0.2827 (4)0.9415 (3)0.0536 (10)
C80.4738 (3)0.2279 (4)0.8831 (3)0.0515 (9)
C90.4461 (3)0.1026 (4)0.8922 (3)0.0629 (11)
H9A0.48050.05050.93780.076*
C100.3699 (3)0.0538 (4)0.8363 (3)0.0624 (10)
C110.3208 (3)0.1285 (4)0.7681 (3)0.0634 (11)
H11A0.26900.09400.72820.076*
C120.3464 (3)0.2513 (4)0.7580 (3)0.0604 (10)
H12A0.31190.30260.71190.072*
C130.4232 (3)0.3012 (4)0.8152 (3)0.0517 (9)
C140.5218 (3)0.4796 (4)0.8538 (3)0.0515 (9)
C150.5407 (3)0.6040 (4)0.8320 (3)0.0533 (10)
C160.6206 (3)0.6586 (4)0.8813 (3)0.0573 (10)
C170.7282 (4)0.9696 (4)0.8798 (4)0.0996 (15)
H17A0.79401.01040.88300.149*
H17B0.68910.99330.93730.149*
H17C0.69280.99600.82000.149*
C180.8048 (4)0.7856 (5)0.7928 (4)0.1052 (16)
H18A0.87210.82170.79850.158*
H18B0.77340.81330.73130.158*
H18C0.80960.69400.79320.158*
C190.4787 (3)0.6755 (4)0.7582 (3)0.0663 (11)
H19A0.40810.64780.76290.080*
H19B0.48110.76570.77510.080*
C200.5124 (3)0.6594 (4)0.6548 (3)0.0754 (12)
H20A0.51300.57610.63040.091*
C210.5412 (4)0.7472 (6)0.5937 (4)0.0971 (16)
C220.5441 (5)0.8841 (6)0.6180 (5)0.150 (3)
H22A0.61080.91750.60390.225*
H22B0.52970.89570.68780.225*
H22C0.49380.92850.57840.225*
C230.5722 (4)0.7131 (7)0.4911 (4)0.150 (3)
H23A0.53400.76340.44370.225*
H23B0.55890.62400.47960.225*
H23C0.64390.72960.48340.225*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.074 (2)0.0613 (19)0.0765 (19)−0.0085 (14)0.0017 (15)0.0073 (14)
O20.0612 (16)0.0555 (17)0.0604 (16)−0.0020 (13)−0.0084 (13)0.0054 (13)
O30.0690 (19)0.0756 (19)0.0669 (18)−0.0041 (14)−0.0158 (15)0.0045 (14)
O40.0730 (19)0.0682 (18)0.0683 (18)0.0026 (14)−0.0207 (15)0.0108 (14)
O50.099 (2)0.0598 (19)0.095 (2)−0.0146 (15)−0.0337 (17)0.0113 (15)
C10.070 (3)0.074 (3)0.083 (3)−0.017 (2)0.005 (3)0.006 (3)
C20.067 (3)0.079 (3)0.081 (3)−0.011 (2)0.000 (2)−0.008 (3)
C30.068 (3)0.075 (3)0.065 (3)−0.004 (2)−0.004 (2)−0.002 (2)
C40.049 (2)0.062 (3)0.055 (2)−0.005 (2)0.0009 (19)−0.001 (2)
C50.050 (2)0.067 (3)0.052 (2)0.009 (2)−0.002 (2)0.004 (2)
C60.046 (2)0.054 (2)0.049 (2)0.0064 (18)0.0004 (18)0.0034 (19)
C70.051 (2)0.059 (3)0.051 (2)0.0056 (19)−0.001 (2)0.006 (2)
C80.053 (2)0.053 (2)0.048 (2)0.0031 (19)−0.0023 (19)0.0026 (19)
C90.067 (3)0.059 (3)0.063 (3)0.007 (2)−0.013 (2)0.002 (2)
C100.068 (3)0.051 (3)0.067 (3)0.001 (2)−0.011 (2)0.003 (2)
C110.066 (3)0.062 (3)0.062 (3)−0.001 (2)−0.013 (2)0.001 (2)
C120.061 (3)0.064 (3)0.055 (2)0.006 (2)−0.011 (2)0.004 (2)
C130.055 (2)0.052 (3)0.048 (2)−0.0012 (19)0.0014 (19)0.0014 (19)
C140.047 (2)0.055 (3)0.053 (2)−0.0028 (18)−0.0011 (19)−0.0026 (19)
C150.054 (2)0.053 (2)0.052 (2)0.0002 (19)0.0054 (19)0.0014 (19)
C160.061 (3)0.056 (3)0.055 (2)−0.003 (2)0.006 (2)0.003 (2)
C170.105 (4)0.076 (3)0.118 (4)−0.027 (3)−0.002 (3)0.008 (3)
C180.104 (4)0.123 (4)0.089 (3)−0.019 (3)0.030 (3)−0.004 (3)
C190.070 (3)0.059 (3)0.070 (3)−0.002 (2)−0.004 (2)0.015 (2)
C200.075 (3)0.085 (3)0.066 (3)0.002 (2)−0.008 (2)0.008 (3)
C210.086 (3)0.128 (5)0.078 (4)−0.023 (3)−0.012 (3)0.034 (3)
C220.181 (6)0.117 (5)0.151 (6)−0.050 (4)−0.026 (5)0.068 (4)
C230.122 (5)0.263 (8)0.065 (4)−0.019 (5)0.005 (3)0.032 (4)
Geometric parameters (Å, º) top
O1—C161.330 (4)C11—C121.335 (5)
O1—C11.446 (4)C11—H11A0.9300
O2—C141.336 (4)C12—C131.360 (5)
O2—C131.348 (4)C12—H12A0.9300
O3—C51.321 (4)C14—C151.357 (5)
O3—H1O30.8200C15—C161.356 (5)
O4—C71.238 (4)C15—C191.474 (5)
O5—C101.334 (4)C17—H17A0.9600
O5—H1O50.8199C17—H17B0.9600
C1—C21.458 (6)C17—H17C0.9600
C1—C181.483 (6)C18—H18A0.9600
C1—C171.488 (6)C18—H18B0.9600
C2—C31.295 (5)C18—H18C0.9600
C2—H2A0.9300C19—C201.464 (5)
C3—C41.414 (5)C19—H19A0.9700
C3—H3A0.9300C19—H19B0.9700
C4—C51.354 (5)C20—C211.287 (6)
C4—C161.374 (5)C20—H20A0.9300
C5—C61.382 (5)C21—C221.468 (8)
C6—C141.371 (5)C21—C231.477 (7)
C6—C71.395 (5)C22—H22A0.9600
C7—C81.421 (5)C22—H22B0.9600
C8—C131.355 (5)C22—H22C0.9600
C8—C91.365 (5)C23—H23A0.9600
C9—C101.340 (5)C23—H23B0.9600
C9—H9A0.9300C23—H23C0.9600
C10—C111.357 (5)
C16—O1—C1118.1 (3)O2—C14—C15115.4 (3)
C14—O2—C13119.8 (3)O2—C14—C6121.1 (3)
C5—O3—H1O3105.6C15—C14—C6123.5 (4)
C10—O5—H1O5108.3C16—C15—C14116.2 (3)
O1—C1—C2109.3 (3)C16—C15—C19121.8 (4)
O1—C1—C18107.3 (4)C14—C15—C19122.0 (4)
C2—C1—C18111.5 (4)O1—C16—C15116.9 (3)
O1—C1—C17103.2 (4)O1—C16—C4119.4 (4)
C2—C1—C17112.7 (4)C15—C16—C4123.6 (4)
C18—C1—C17112.2 (4)C1—C17—H17A109.5
C3—C2—C1121.1 (4)C1—C17—H17B109.5
C3—C2—H2A119.5H17A—C17—H17B109.5
C1—C2—H2A119.5C1—C17—H17C109.5
C2—C3—C4119.9 (4)H17A—C17—H17C109.5
C2—C3—H3A120.1H17B—C17—H17C109.5
C4—C3—H3A120.1C1—C18—H18A109.5
C5—C4—C16117.9 (4)C1—C18—H18B109.5
C5—C4—C3123.6 (4)H18A—C18—H18B109.5
C16—C4—C3118.5 (4)C1—C18—H18C109.5
O3—C5—C4118.6 (4)H18A—C18—H18C109.5
O3—C5—C6120.2 (4)H18B—C18—H18C109.5
C4—C5—C6121.3 (3)C20—C19—C15113.8 (3)
C14—C6—C5117.4 (4)C20—C19—H19A108.8
C14—C6—C7120.7 (4)C15—C19—H19A108.8
C5—C6—C7121.9 (3)C20—C19—H19B108.8
O4—C7—C6122.0 (4)C15—C19—H19B108.8
O4—C7—C8121.2 (3)H19A—C19—H19B107.7
C6—C7—C8116.7 (3)C21—C20—C19127.5 (5)
C13—C8—C9118.3 (3)C21—C20—H20A116.3
C13—C8—C7119.4 (4)C19—C20—H20A116.3
C9—C8—C7122.2 (3)C20—C21—C22124.2 (5)
C10—C9—C8120.8 (4)C20—C21—C23120.0 (6)
C10—C9—H9A119.6C22—C21—C23115.7 (5)
C8—C9—H9A119.6C21—C22—H22A109.5
O5—C10—C9123.1 (4)C21—C22—H22B109.5
O5—C10—C11117.0 (4)H22A—C22—H22B109.5
C9—C10—C11119.9 (4)C21—C22—H22C109.5
C12—C11—C10120.3 (4)H22A—C22—H22C109.5
C12—C11—H11A119.8H22B—C22—H22C109.5
C10—C11—H11A119.8C21—C23—H23A109.5
C11—C12—C13119.8 (4)C21—C23—H23B109.5
C11—C12—H12A120.1H23A—C23—H23B109.5
C13—C12—H12A120.1C21—C23—H23C109.5
O2—C13—C8122.2 (3)H23A—C23—H23C109.5
O2—C13—C12117.0 (3)H23B—C23—H23C109.5
C8—C13—C12120.8 (4)
C16—O1—C1—C2−43.1 (5)C14—O2—C13—C12−178.1 (3)
C16—O1—C1—C1878.0 (4)C9—C8—C13—O2179.6 (3)
C16—O1—C1—C17−163.3 (3)C7—C8—C13—O2−1.0 (5)
O1—C1—C2—C331.7 (6)C9—C8—C13—C120.3 (5)
C18—C1—C2—C3−86.9 (5)C7—C8—C13—C12179.7 (3)
C17—C1—C2—C3145.9 (4)C11—C12—C13—O2−179.8 (3)
C1—C2—C3—C4−5.5 (6)C11—C12—C13—C8−0.4 (5)
C2—C3—C4—C5170.6 (4)C13—O2—C14—C15177.4 (3)
C2—C3—C4—C16−12.8 (6)C13—O2—C14—C6−2.3 (5)
C16—C4—C5—O3−179.3 (3)C5—C6—C14—O2180.0 (3)
C3—C4—C5—O3−2.6 (5)C7—C6—C14—O20.5 (5)
C16—C4—C5—C60.7 (5)C5—C6—C14—C150.3 (5)
C3—C4—C5—C6177.3 (3)C7—C6—C14—C15−179.1 (3)
O3—C5—C6—C14178.2 (3)O2—C14—C15—C16−177.6 (3)
C4—C5—C6—C14−1.7 (5)C6—C14—C15—C162.1 (5)
O3—C5—C6—C7−2.4 (5)O2—C14—C15—C191.8 (5)
C4—C5—C6—C7177.7 (3)C6—C14—C15—C19−178.5 (3)
C14—C6—C7—O4−178.1 (3)C1—O1—C16—C15−155.5 (3)
C5—C6—C7—O42.4 (5)C1—O1—C16—C428.4 (5)
C14—C6—C7—C81.0 (5)C14—C15—C16—O1−179.2 (3)
C5—C6—C7—C8−178.4 (3)C19—C15—C16—O11.4 (5)
O4—C7—C8—C13178.4 (3)C14—C15—C16—C4−3.3 (5)
C6—C7—C8—C13−0.8 (5)C19—C15—C16—C4177.3 (3)
O4—C7—C8—C9−2.2 (5)C5—C4—C16—O1177.8 (3)
C6—C7—C8—C9178.6 (3)C3—C4—C16—O11.0 (5)
C13—C8—C9—C10−0.8 (5)C5—C4—C16—C152.0 (6)
C7—C8—C9—C10179.8 (3)C3—C4—C16—C15−174.8 (3)
C8—C9—C10—O5−178.6 (3)C16—C15—C19—C2094.2 (4)
C8—C9—C10—C111.4 (6)C14—C15—C19—C20−85.2 (5)
O5—C10—C11—C12178.5 (4)C15—C19—C20—C21−121.4 (5)
C9—C10—C11—C12−1.5 (6)C19—C20—C21—C22−0.8 (8)
C10—C11—C12—C131.0 (6)C19—C20—C21—C23−179.6 (4)
C14—O2—C13—C82.5 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H1O3···O40.821.772.520 (3)152
O5—H1O5···O4i0.821.892.679 (4)160
C11—H11A···O3ii0.932.583.352 (5)141
C12—H12A···O5iii0.932.503.352 (5)152
Symmetry codes: (i) −x+1, −y, −z+2; (ii) x−3/2, −y−1/2, z−3/2; (iii) −x+1/2, y+1/2, −z+3/2.
 

Acknowledgements

The authors would like to the Sarawak Research Development Council (SRDC) (RDCRG/CAT/2019/11) and Universiti Teknologi MARA (UiTM) for financial assistance and support given throughout the research conducted on the genus Calophyllum. The Sarawak Biodiversity Centre (SBC) is also acknowledged for providing a research permit (SBC-2022-RDP-40-VJYM).

Funding information

Funding for this research was provided by: Sarawak Research Development Council (SRDC) (grant No. RDCRG/CAT/2019/11).

References

First citationAminudin, N. I., Ahmad, F., Taher, M. & Zulkifli, R. M. (2015). Nat. Prod. Commun. 10, 1585–1587.  Web of Science PubMed Google Scholar
 First citationBruker (2012). APEX2, SAINT, and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationFilho, V. C., Meyre-Silva, C. & Niero, R. (2009). Chem. Biodivers. B, 6, 313–327.  Google Scholar
 First citationCorner, E. J. H. (1952). Wayside Trees of Malaya, Vol. 1. Singapore: The Government Printing Office.  Google Scholar
 First citationCrane, S., Aurore, G., Joseph, H., Mouloungui, Z. & Bourgeois, P. (2005). Phytochemistry, 66, 1825–1831.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationCremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.  CrossRef CAS Web of Science Google Scholar
 First citationDweck, A. & Meadows, T. (2002). Int. J. Cosmet. Sci. 24, 341–348.  CrossRef PubMed CAS Google Scholar
 First citationEe, G. C. L., Mah, S. H., Teh, S. S., Rahmani, M., Go, R. & Taufiq-Yap, Y. H. (2011). Molecules, 16, 9721–9727.  Web of Science CrossRef CAS PubMed Google Scholar
 First citationEe, G. C. L., Sim, W. C., Kwong, H. C., Mohamed Tahir, M. I. & Silong, S. (2010). Acta Cryst. E66, o3362–o3363.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationGuilet, D., Hélesbeux, J.-J., Séraphin, D., Sévenet, T., Richomme, P. & Bruneton, J. (2001). J. Nat. Prod. 64, 563–568.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationGupta, S. & Gupta, P. (2020). Bioactive Nat. Prod. Drug Discov. 8, 215–242.  CrossRef Google Scholar
 First citationIto, C., Itoigawa, M., Mishina, Y., Filho, V. C., Mukainaka, T., Tokuda, H., Nishino, H. & Furukawa, H. (2002). J. Nat. Prod. 65, 267–272.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationKarunakaran, T., Firouz, N. S., Santhanam, R. & Jong, V. Y. M. (2022). Nat. Prod. Res. 36, 654–659.  Web of Science CrossRef CAS PubMed Google Scholar
 First citationLi, W., Guo, Y., Zhang, C., Wu, R., Yang, A. Y., Gaspar, J. & Kong, A.-N. T. (2016). Chem. Res. Toxicol. 29, 2071–2095.  Web of Science CrossRef CAS PubMed Google Scholar
 First citationLim, C. K., Ham, Y. P., Lim, L. Q. & Jong, V. Y. M. (2019). Phytochemistry Lett. 30, 99–102.  Web of Science CrossRef CAS Google Scholar
 First citationLim, C.-K., Hemaroopini, S., Say, Y.-H. & Jong, V. Y.-M. (2017). Nat. Prod. Commun. 12, 1469–1471.  Google Scholar
 First citationMah, S. H., Ee, G. C. L., Teh, S. S., Rahmani, M., Lim, Y. M. & Go, R. (2012). Molecules, 17, 8303–8311.  Web of Science CrossRef CAS PubMed Google Scholar
 First citationReyes-Chilpa, R., Estrada-Muñiz, E., Ram\?írez Apan, T., Amekraz, B., Aumelas, A., Jankowski, C. K. & Vázquez-Torres, M. (2004). Life Sci. 75, 1635–1647.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2015a). Acta Cryst. A71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2015b). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
 First citationSpek, A. L. (2020). Acta Cryst. E76, 1–11.  Web of Science CrossRef IUCr Journals Google Scholar
 First citationThiagarajan, S., Yong, F.-L., Subramaniam, H., Jong, V. Y.-M., Lim, C.-K. & Say, Y.-H. (2017). Trop. J. Pharm. Res. 16, 563–572.  Web of Science CrossRef CAS Google Scholar
 First citationWang, Z., Sun, F., Wang, J., Dong, J., Xie, S., Sun, M. & Sun, B. (2019). Historical Biology, 31, 1379–1393.  Web of Science CrossRef Google Scholar
 First citationZamakshshari, N. H., Ee, G. C. L., Ismail, I. S., Ibrahim, Z. & Mah, S. H. (2019). Food Chem. Toxicol. 133, 110800.  Web of Science CrossRef PubMed Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 8| Part 1| January 2023| x221198
https://doi.org/10.1107/S2414314622011981