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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 82| Part 6| June 2026| Pages 738-742
https://doi.org/10.1107/S2056989026005360

Crystal structure and Hirshfeld surface analysis of 3-acetyl-11-keto-β-boswellic acid

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B. Dinesh,a H. N. Shafiulla,a J. C. Shwetha,b A. H. Udaya Kumar,c N. K. Lokanathd and K. Anand Solomona*

aDepartment of Phytochemistry, Greenspace Herbs, Brigade Twin Towers, Yeshwanthpur, Bengaluru-560022. Karnataka, India, bDepartment of Chemistry, Sri Sathya Sai University for Human Excellence, Nallakadirenahalli, 561211, India, cDepartment of Physics, Seshadripuram Institute of Technology, Kadakola industrial area, Mysore 571311, Karnataka, India, and dDepartment of Studies in Physics, University of Mysore, Mysuru 570006, Karnataka, India
*Correspondence e-mail: [email protected]

Edited by F. F. Ferreira, Universidade Federal do ABC, Brazil (Received 10 April 2026; accepted 21 May 2026; online 29 May 2026)

Acetyl-11-keto-β-boswellic acid, C32H48O5, a penta­cyclic triterpenoid from Boswellia serrata, exhibits notable anti-inflammatory and pharmacological activities. The compound crystallizes in the ortho­rhom­bic space group P21212 and exhibits a rigid penta­cyclic framework with eleven stereogenic centers. The cyclo­hexane rings adopt near-ideal chair conformations with minimal steric strain. The crystal packing is governed by O—H⋯O hydrogen bonds, forming zigzag chains along the [100] direction and extending into a three-dimensional network and is further consolidated by van der Waals inter­actions. Hirshfeld surface analysis shows dominant H⋯H contacts (91.5%), highlighting the importance of van der Waals forces, while H⋯O/O⋯H contacts provide localized stabilization.

CCDC reference: 2555762

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1. Chemical context

Acetyl-11-keto-β-boswellic acid (AKBA) is a natural compound isolated from the dried gum resin of Boswellia Serrata. It belongs to ursane-type penta­cyclic triterpene class, containing fused cyclo­hexane rings. The mol­ecule bears several oxygen-containing functional groups, including carb­oxy­lic acid, ketone, and acetyl substituents (Park et al., 2002View full citation), which contribute to inter­molecular inter­actions within the crystal. The cardioprotective activity of these compounds has been recorded (Teng et al., 2024View full citation). AKBA exhibits inhibitory effects on cultured human umbilical vascular endothelial cells (Shen et al., 2015View full citation), and also exhibits anti-proliferative (Li et al., 2022View full citation), and anti-dermatitis (Tsai et al., 2022View full citation) activity. It functions as a selective inhibitor of 5-lipoxygenase, a key enzyme in leukotriene biosynthesis, with demonstrated anti-inflammatory and anti-arthritic activity (Sailer et al., 1996View full citation). The mol­ecule's lipophilic nature, inherent to its steroid-like scaffold, presents formulation challenges but also enables membrane permeability and inter­action with hydro­phobic enzyme active sites (Lindner et al., 2026View full citation).

[Scheme 1]

2. Structural commentary

The title mol­ecule (Fig. 1[link]) crystallizes in ortho­rhom­bic system, space group P21212, with four mol­ecules in the unit cell (Z = 4). AKBA possesses eleven stereogenic centres – C3, C4, C5, C8, C9, C17, C18, C20 in the R configuration and C10, C14, C19 in the S configuration. The acet­oxy group is at the α position (Ito et al., 2025aView full citation). This forces a planar arrangement of the six atoms O3/C9/C11–C14, with deviations from the least-square plane being less than 0.036 Å. The five six-membered rings are fused in such a manner that the C—C bonds occupy equatorial positions, except for the C18—C19 bond, which is in an axial position with respect to the C13–C18 ring. As a consequence, all cyclo­hexane rings form a sheet-like structure, apart from the C17–C22 ring, which is oriented roughly orthogonal to this plane [C13—C18—C17—C22 = 174.78 (4)°]. A puckering analysis of conformational characteristics of the fused six-membered rings according to the Cremer-Pople approach was qu­anti­tatively evaluated and revealed that the crystal structure exhibits mainly distorted chair-like conformational forms.

[Figure 1]
Figure 1
Acetyl-11-keto-β-boswellic acid (AKBA) showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level, and hydrogen atoms are omitted for clarity.

For Ring (1) (C1–C5/C10), the puckering parameters are Q = 0.541 (4) Å, θ = 5.9 (4)° and φ = 320 (4)° indicating an almost ideal chair conformation. The very small θ value together with the dominant Q(3) contribution [0.538 (4) Å] confirms that the ring closely resembles a classical cyclo­hexane chair geometry. This assignment is further supported by the alternating torsion angles ranging from −55.2 (4) to 55.1 (4)° and by the Evans–Boeyens conformational analysis, which describes the ring as very similar to a C-form.

Ring (2) (C5–C10) also adopts a chair conformation with puckering parameters Q = 0.547 (4) Å, θ = 13.4 (4)° and φ = 25.3 (16)°. Although the θ value is slightly larger than that observed for Ring (1), the dominant Q(3) term [0.532 (4) Å] clearly establishes a chair-type geometry with minor distortion. The observed torsion angles, varying between −63.3 (4) and 57.9 (4)°, are consistent with a puckered cyclo­hexane framework.

In contrast, Ring (3) (C8/C9/C11–C14) exhibits a significantly distorted conformation arising from the presence of sp2-hybridized atoms within the ring skeleton. The Cremer–Pople parameters [Q = 0.563 (4) Å, θ = 54.4 (4)°, φ = 6.5 (5)°] indicate a conformation inter­mediate between a half-chair and twist-boat geometry. The comparatively large Q(2) value [0.458 (4) Å] demonstrates a substantial deviation from an ideal chair form, while the reduced average torsion angle of approximately 40.7° further supports the presence of conformational distortion induced by partial unsaturation.

Ring (4) (C13–C18) adopts an inverted chair conformation, as evidenced by the puckering parameters Q = 0.517 (4) Å, θ = 160.4 (4)°, and φ = 41.8 (14)°. The θ value approaching 180° is characteristic of an inverted-chair geometry, while the dominant negative Q(3) component [−0.487 (4) Å] further substanti­ates this assignment. The alternating torsion angles observed within the ring are typical of a puckered six-membered ring adopting a chair-like arrangement with slight distortion due to substitution effects.

Similarly, Ring (5) (C17–C22) displays a near-ideal inverted-chair conformation with puckering parameters Q = 0.528 (5) Å, θ = 174.0 (5)° and φ = 27 (5)°. The negligible Q(2) contribution together with the dominant negative Q(3) value [−0.525 (5) Å] confirms the highly stable chair geometry. The Evans–Boeyens analysis also classifies this ring as being very close to a C-form conformation.

The six-membered ring is composed of sp3-hybridized atoms, with normal bond lengths between carbon atoms (1.5416 Å) and bond angles close to tetra­hedral, suggesting a strain-free saturated ring system. The presence of alternating torsion angles, approximately ±50°, together with small deviations from planarity, is consistent with a puckered ring conformation

3. Supra­molecular features and Hirshfeld surface analysis

In the extended structure of AKBA, the mol­ecules are linked by O—H⋯O hydrogen bonds (Table 1[link]) from the carb­oxy­lic acid OH group to the carbonyl oxygen atom, forming a C4 zigzag chain propagating along the [100] direction (Fig. 2[link]). The hydro­carbon framework of the mol­ecule forms hydro­phobic regions, while the oxygenated functional groups participate in hydrogen bonding, leading to an organized packing arrangement within the ortho­rhom­bic structure.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O4—H4⋯O1i 0.82 1.91 2.695 (4) 161
C1—H1A⋯O5 0.97 2.39 3.023 (5) 122
C25—H25C⋯O5 0.96 2.38 3.058 (5) 127
C30—H30B⋯O1ii 0.96 2.60 3.468 (6) 151
C32—H32C⋯O3iii 0.96 2.52 3.445 (6) 162
Symmetry codes: (i) Mathematical equation; (ii) Mathematical equation; (iii) Mathematical equation.
[Figure 2]
Figure 2
Crystal packing of acetyl-11-keto-β-boswellic acid (AKBA) viewed along the c axis, illustrating the mol­ecular arrangement within the unit cell. Inter­molecular inter­actions and packing orientation are highlighted, and the unit-cell boundaries are shown.

The Hirshfeld surface mapped over dnorm for AKBA reveals localized red regions corresponding to short inter­molecular contacts involving oxygen-containing functional groups. These red spots are associated mainly with close H⋯O/O⋯H inter­actions involving the acetyl, keto and carb­oxy­lic oxygen atoms, indicating contacts shorter than the sum of the corresponding van der Waals radii. White areas correspond to contacts close to van der Waals separations, whereas blue regions represent distances longer than the van der Waals radii and therefore weaker inter­molecular contacts.

The Hirshfeld surface area was calculated as 509.74 Å, with a surface volume of 755.63 Å. The globularity value of 0.787 indicates a compact but slightly elongated mol­ecular envelope consistent with the rigid penta­cyclic triterpenoid framework, whereas the asphericity value of 0.187 reflects moderate anisotropy arising from the extended substituent groups. Two-dimensional fingerprint plots show that H⋯H contacts dominate the crystal packing, contributing 91.5% of the total Hirshfeld surface. The broad central distribution in the H⋯H fingerprint plot reflects extensive hydro­carbon–hydro­carbon inter­actions arising from the large penta­cyclic triterpenoid framework, confirming that van der Waals inter­actions are the principal consolidating force in the crystal. H⋯O/O⋯H contacts contribute 8.3% of the Hirshfeld surface and appear as distinct sharp spikes in the fingerprint plot. These spikes correspond to short inter­molecular contacts involving oxygen acceptor atoms and indicate weak C—H⋯O inter­actions that provide localized consolidation around the polar functional groups. The reciprocal O⋯H/H⋯O contribution amounts to 17.6% when reciprocal contacts are considered, reflecting the combined donor–acceptor inter­action environment surrounding the oxygen atoms. C⋯H/H⋯C contacts contribute only 0.2% of the surface and are represented by small isolated wing-like regions, indicating that weak hydro­phobic carbon–hydrogen contacts make only a minor contribution to crystal packing. C⋯O/O⋯C inter­actions are negligible (0.1–0.2%), showing that direct carbon­yl–carbon contacts are not significant in the present crystal structure (Fig. 3[link]). The Hirshfeld surface mapped over dnorm displays several small bright-red spots, corresponding to weak and longer range inter­actions that contribute to the consolidation of the packing (Fig. 4[link]). The fragment patch highlights key neighbouring mol­ecular inter­actions contributing to the crystal packing. The curvedness map indicates predominantly flat regions, suggesting the absence of significant π–π stacking inter­actions. The shape-index surface shows complementary patterns, confirming localized inter­molecular contacts such as hydrogen bonding (Fig. 5[link]).

[Figure 3]
Figure 3
Hirshfeld surface fingerprint plots for acetyl-11-keto-β-boswellic acid (AKBA) showing the contributions of different inter­molecular contacts: H⋯O/O⋯H, H⋯H, C⋯H/H⋯C, and all contacts (ALL and ALL–H). The blue regions represent the specific inter­actions within the mol­ecule, while the grey areas correspond to the overall fingerprint plots. These plots highlight the dominant role of H⋯H and H⋯O inter­actions in consolidating the crystal packing.
[Figure 4]
Figure 4
Hirshfeld surfaces mapped over dnorm: (a) front view and (b) side view showing short inter­molecular contacts as red regions.
[Figure 5]
Figure 5
Hirshfeld surfaces mapped over (a) fragment patch, (b) curvedness and (c) shape-index, showing neighbouring mol­ecular fragments and local surface features associated with the inter­molecular packing.

4. Database survey

A search of the Cambridge Structural Database (CSD, version 6.00 update of May 2025; Groom et al., 2016View full citation) for compounds containing the boswellic acid skeleton shows that only a limited number of crystal structures of boswellic acid derivatives have been reported. These include β-boswellic acid, acetyl-β-boswellic acid, and 11-keto-β-boswellic acid derivatives (Majeed et al., 2024View full citation; Ito et al., 2025bView full citation). These compounds share the same penta­cyclic triterpenoid framework composed of fused cyclo­hexane rings, adopting stable chair or slightly distorted chair conformations. In all the structures, the stereochemistry at the ring junctions remains conserved, confirming that chemical modifications at peripheral positions do not significantly alter the rigid triterpenoid backbone. Comparison with previously reported boswellic acid structures indicates that the overall structure conforms with those with other derivatives of the boswellic acid family (Fig. 6[link]). However, substitution at the C3 and C11 positions significantly influences the inter­molecular inter­actions and crystal packing (Al-Harrasi et al., 2018View full citation). In β-boswellic acid, the hydroxyl group at C3 can participate as a hydrogen-bond donor, frequently forming inter­molecular O—H⋯O hydrogen bonds that contribute to crystal cohesion. In addition, the compound contains an acetyl group at C3, which replaces the hydroxyl donor with an ester carbonyl acceptor, thereby reducing classical hydrogen-bonding capability (Khaafi & Javadi, 2023View full citation)

[Figure 6]
Figure 6
Superimposed mol­ecular structures of boswellic acid derivatives showing conformational differences: acetyl β-boswellic acid (blue), 11-keto-β-boswellic acid (red) and acetyl-11-keto-β-boswellic acid (green).

5. Synthesis and crystallization

Fresh frankincense resin lumps of 6 g were ground to a fine, uniform powder with a mortar and pestle. Primarily, 100 mg of powdered resin was transferred into a 2 mL reaction tube and 1 mL of extraction solvent (methanol: 1% aqueous formic acid, 65:35 v/v) was added. To promote efficient release of triterpenes, the suspension was sonicated at 298 K for 10 minutes and then centrifuged at 14,000 r.p.m. for 5 minutes; the clear supernatant was deca­nted and reserved. The pooled AKBA-rich supernatent was subjected to flash chromatography on silica (230–400 mesh) using n-hexane (solvent A) and ethyl acetate (solvent B) with a gentle gradient (flow ≃ 1 mL min−1), guided by TLC. Fractions eluting at ∼40–50% EtOAc were concentrated under reduced pressure at low bath temperature. Residual non-polar impurities were removed by washing the concentrate with cold n-hexane; the remaining polar residue was dissolved in minimum hot aceto­nitrile and allowed to cool slowly to room temperature (Gupta et al., 2021View full citation; Lauss et al., 2024View full citation). The resulting pale-white crystals were collected by filtration and dried under vacuum. Equimolar qu­anti­ties (1:1 stoichiometric ratio) of AKBA crystals and cinnamic acid were dissolved in hot ethanol to obtain a clear homogeneous solution. The resulting solution was then allowed to cool slowly and allowed slow evaporation to obtain crystals suitable for SXRD analysis.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. All hydrogen atoms were placed at idealized positions C—H = 0.96–0.98 Å) and refined using a riding model with Uiso(H) = 1.2–1.5Ueq(C). The assignment of the absolute configuration is based on IUPAC nomenclature.

Table 2
Experimental details

Crystal data
Chemical formula C32H48O5
Mr 512.70
Crystal system, space group Orthorhombic, P21212
Temperature (K) 293
a, b, c (Å) 11.8995 (8), 16.3460 (9), 15.7065 (9)
V (Å3) 3055.0 (3)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.07
Crystal size (mm) 0.26 × 0.24 × 0.22
 
Data collection
Diffractometer Rigaku model?
Absorption correction Multi-scan (CrysAlis PRO; Rigaku OD, 2024View full citation)
Tmin, Tmax 0.981, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections 21419, 6775, 3256
Rint 0.071
(sin θ/λ)max (Å−1) 0.662
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.058, 0.155, 0.95
No. of reflections 6775
No. of parameters 344
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.17, −0.16
Absolute structure Flack x determined using 990 quotients [(I+)−(I−)]/[(I+)+(I−)] (Parsons et al., 2013View full citation)
Absolute structure parameter 0.6 (10)
Computer programs: CrysAlis PRO (Rigaku OD, 2024View full citation), SHELXS (Sheldrick, 2008View full citation), SHELXL2018/3 (Sheldrick, 2015View full citation) and OLEX2 (Dolomanov et al., 2009View full citation).

Supporting information

CCDC reference: 2555762

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989026005360/ee2029sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989026005360/ee2029Isup3.hkl

checkCIF report


Computing details top

3-Acetyl-11-keto-β-boswellic acid top
Crystal data top
C32H48O5Dx = 1.115 Mg m−3
Mr = 512.70Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P21212Cell parameters from 6775 reflections
a = 11.8995 (8) Åθ = 1.8–28.1°
b = 16.3460 (9) ŵ = 0.07 mm−1
c = 15.7065 (9) ÅT = 293 K
V = 3055.0 (3) Å3Rock, white
Z = 40.26 × 0.24 × 0.22 mm
F(000) = 1120
Data collection top
Rigaku model?
diffractometer		3256 reflections with I > 2σ(I)
Multi–scanRint = 0.071
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2024)		θmax = 28.1°, θmin = 1.8°
Tmin = 0.981, Tmax = 0.984h = −15→13
21419 measured reflectionsk = −21→20
6775 independent reflectionsl = −16→20
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.0631P)2]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.058(Δ/σ)max = 0.004
wR(F2) = 0.155Δρmax = 0.17 e Å−3
S = 0.95Δρmin = −0.16 e Å−3
6775 reflectionsExtinction correction: SHELXL-2018/3 (Sheldrick 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
344 parametersExtinction coefficient: 0.0054 (14)
0 restraintsAbsolute structure: Flack x determined using 990 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Hydrogen site location: inferred from neighbouring sitesAbsolute structure parameter: 0.6 (10)
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C180.8263 (3)0.1344 (2)0.8671 (2)0.0647 (10)
H180.9047940.1270920.8499520.078*
O20.6711 (2)0.28353 (14)1.38435 (16)0.0754 (8)
C90.8163 (3)0.14879 (19)1.1508 (2)0.0547 (9)
H90.7742990.1993661.1404040.066*
C50.7083 (3)0.1303 (2)1.2877 (2)0.0584 (10)
H50.6631790.1756291.2653160.070*
C130.8257 (3)0.1324 (2)0.9645 (2)0.0581 (10)
C100.8270 (3)0.14465 (19)1.2504 (2)0.0565 (9)
C110.9241 (3)0.1600 (2)1.1012 (3)0.0635 (10)
C70.6369 (3)0.0635 (2)1.1551 (2)0.0654 (10)
H7A0.5843220.1078901.1455850.079*
H7B0.6033230.0139021.1327520.079*
C30.7493 (4)0.2204 (2)1.4153 (3)0.0691 (11)
H30.7531620.2220891.4776130.083*
C60.6541 (3)0.0534 (2)1.2496 (2)0.0678 (11)
H6A0.7020460.0065121.2601580.081*
H6B0.5822920.0435241.2769250.081*
C120.9183 (3)0.15086 (19)1.0080 (3)0.0621 (10)
H120.9841900.1585880.9772350.075*
C40.6985 (3)0.1387 (2)1.3861 (2)0.0656 (11)
O40.7212 (3)−0.00278 (16)1.41652 (18)0.1025 (11)
H40.735364−0.0353661.4547470.154*
C10.8679 (3)0.2302 (2)1.2813 (3)0.0677 (11)
H1A0.9442790.2389671.2617240.081*
H1B0.8208610.2721441.2560370.081*
C160.6425 (3)0.0608 (3)0.8678 (3)0.0859 (13)
H16A0.6051780.1116220.8530100.103*
H16B0.5999110.0163170.8427250.103*
O51.0147 (2)0.17837 (18)1.13377 (17)0.0879 (9)
C80.7460 (3)0.08150 (18)1.1051 (2)0.0555 (9)
C20.8643 (4)0.2384 (2)1.3777 (3)0.0761 (12)
H2A0.9187510.2011621.4024200.091*
H2B0.8862170.2936231.3931600.091*
C150.6423 (4)0.0511 (2)0.9652 (3)0.0806 (13)
H15A0.667898−0.0035450.9794150.097*
H15B0.5657500.0565920.9857660.097*
C190.7893 (3)0.2195 (2)0.8309 (2)0.0696 (11)
H190.7129480.2302560.8514410.083*
C140.7174 (3)0.1142 (2)1.0119 (2)0.0595 (9)
C170.7617 (4)0.0611 (2)0.8298 (3)0.0804 (12)
O30.8236 (3)0.08341 (17)1.4943 (2)0.0934 (10)
C270.6491 (3)0.1955 (2)1.0140 (3)0.0726 (11)
H27A0.6991870.2404491.0244650.109*
H27B0.5940320.1928631.0585630.109*
H27C0.6121700.2032540.9602960.109*
O10.7217 (3)0.36657 (16)1.4882 (2)0.1078 (12)
C230.7574 (4)0.0711 (2)1.4386 (3)0.0768 (12)
C260.8150 (3)0.0004 (2)1.1019 (3)0.0733 (11)
H26A0.8895300.0117471.0816310.110*
H26B0.778888−0.0375381.0641710.110*
H26C0.819116−0.0227621.1579620.110*
C240.5746 (4)0.1356 (2)1.4149 (3)0.0872 (13)
H24A0.5310340.1729391.3812070.131*
H24B0.5696260.1508491.4738280.131*
H24C0.5460790.0811161.4076680.131*
C250.9125 (3)0.0795 (2)1.2798 (3)0.0734 (11)
H25A0.8804350.0259691.2729720.110*
H25B0.9307770.0882411.3386040.110*
H25C0.9795020.0836311.2459950.110*
C200.7854 (4)0.2204 (3)0.7323 (3)0.0883 (13)
H200.8621990.2119590.7115370.106*
C220.7544 (5)0.0691 (3)0.7322 (3)0.1049 (16)
H22A0.8282390.0586150.7084620.126*
H22B0.7042660.0269180.7109920.126*
C310.6617 (4)0.3518 (2)1.4287 (3)0.0771 (12)
C320.5735 (4)0.4064 (2)1.3955 (3)0.0976 (14)
H32A0.5632880.3964681.3357550.146*
H32B0.5954760.4623391.4040770.146*
H32C0.5043130.3960881.4250050.146*
C290.8637 (4)0.2875 (3)0.8631 (3)0.0955 (14)
H29A0.8600740.2895200.9241690.143*
H29B0.8386360.3387660.8400760.143*
H29C0.9398560.2776190.8457140.143*
C210.7141 (5)0.1502 (4)0.6997 (3)0.1055 (16)
H21A0.6368050.1584260.7174320.127*
H21B0.7158250.1499030.6379990.127*
C280.8231 (5)−0.0187 (3)0.8530 (3)0.1089 (16)
H28A0.893397−0.0211010.8230390.163*
H28B0.777492−0.0646420.8371090.163*
H28C0.836816−0.0200160.9131690.163*
C300.7443 (5)0.3010 (3)0.6975 (3)0.1197 (18)
H30A0.6719660.3133230.7212630.179*
H30B0.7384400.2975570.6366660.179*
H30C0.7965120.3434260.7124800.179*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C180.055 (2)0.065 (2)0.074 (3)−0.0002 (19)0.010 (2)−0.0078 (19)
O20.095 (2)0.0501 (14)0.0807 (17)0.0167 (14)−0.0065 (15)−0.0069 (13)
C90.047 (2)0.0423 (18)0.075 (3)−0.0010 (16)−0.0059 (19)0.0048 (17)
C50.056 (2)0.0433 (19)0.076 (3)−0.0002 (16)−0.004 (2)0.0051 (17)
C130.048 (2)0.0461 (19)0.081 (3)0.0030 (17)0.003 (2)−0.0013 (18)
C100.050 (2)0.0402 (18)0.080 (3)0.0024 (17)−0.0068 (19)0.0021 (17)
C110.044 (2)0.057 (2)0.090 (3)−0.0059 (18)−0.004 (2)0.008 (2)
C70.055 (2)0.060 (2)0.081 (3)−0.0107 (19)0.000 (2)0.0023 (19)
C30.088 (3)0.050 (2)0.069 (2)0.010 (2)−0.010 (2)0.0003 (18)
C60.067 (3)0.056 (2)0.081 (3)−0.009 (2)0.003 (2)0.0057 (19)
C120.044 (2)0.062 (2)0.080 (3)−0.0035 (18)0.005 (2)0.004 (2)
C40.075 (3)0.047 (2)0.075 (3)0.0000 (18)−0.004 (2)−0.0002 (19)
O40.160 (3)0.0521 (16)0.095 (2)−0.0083 (18)−0.029 (2)0.0153 (15)
C10.062 (2)0.055 (2)0.087 (3)−0.0079 (19)−0.011 (2)−0.002 (2)
C160.069 (3)0.105 (3)0.084 (3)−0.026 (3)−0.002 (2)−0.018 (2)
O50.0552 (18)0.111 (2)0.097 (2)−0.0199 (15)−0.0107 (16)0.0098 (17)
C80.043 (2)0.0477 (18)0.076 (2)−0.0030 (16)−0.0002 (19)0.0029 (18)
C20.088 (3)0.049 (2)0.091 (3)0.000 (2)−0.027 (3)−0.008 (2)
C150.061 (3)0.097 (3)0.084 (3)−0.024 (2)−0.001 (2)−0.006 (2)
C190.061 (3)0.077 (3)0.071 (3)0.004 (2)0.005 (2)0.003 (2)
C140.044 (2)0.060 (2)0.074 (2)−0.0042 (17)−0.0025 (19)0.0024 (19)
C170.078 (3)0.082 (3)0.082 (3)−0.013 (3)0.011 (3)−0.019 (2)
O30.120 (3)0.0680 (18)0.092 (2)0.0050 (17)−0.027 (2)0.0057 (16)
C270.053 (2)0.085 (3)0.080 (3)0.017 (2)0.004 (2)0.009 (2)
O10.176 (3)0.0553 (16)0.092 (2)0.0202 (19)−0.026 (2)−0.0187 (16)
C230.103 (4)0.046 (2)0.081 (3)0.005 (2)0.001 (3)0.005 (2)
C260.070 (3)0.051 (2)0.099 (3)−0.0016 (18)−0.003 (2)−0.001 (2)
C240.089 (3)0.076 (3)0.097 (3)0.001 (2)0.022 (3)−0.002 (2)
C250.067 (3)0.063 (2)0.090 (3)0.012 (2)−0.008 (2)0.008 (2)
C200.087 (3)0.101 (3)0.076 (3)−0.004 (3)0.015 (3)−0.005 (3)
C220.108 (4)0.113 (4)0.094 (4)−0.029 (4)0.014 (3)−0.035 (3)
C310.107 (4)0.049 (2)0.076 (3)0.001 (2)0.006 (3)−0.002 (2)
C320.109 (4)0.062 (2)0.122 (4)0.024 (3)0.010 (3)0.006 (3)
C290.108 (4)0.075 (3)0.103 (3)−0.009 (3)−0.017 (3)0.010 (2)
C210.114 (4)0.129 (4)0.074 (3)−0.011 (4)0.003 (3)−0.006 (3)
C280.118 (4)0.068 (3)0.141 (4)−0.005 (3)0.005 (3)−0.025 (3)
C300.146 (5)0.122 (4)0.091 (3)0.018 (4)0.002 (4)0.027 (3)
Geometric parameters (Å, º) top
C18—H180.9800C15—H15A0.9700
C18—C131.530 (5)C15—H15B0.9700
C18—C191.566 (5)C15—C141.549 (5)
C18—C171.539 (5)C19—H190.9800
O2—C31.472 (4)C19—C201.549 (6)
O2—C311.320 (5)C19—C291.510 (5)
C9—H90.9800C14—C271.558 (5)
C9—C101.571 (5)C17—C221.541 (6)
C9—C111.511 (5)C17—C281.539 (6)
C9—C81.558 (4)O3—C231.195 (5)
C5—H50.9800C27—H27A0.9600
C5—C101.547 (5)C27—H27B0.9600
C5—C61.534 (5)C27—H27C0.9600
C5—C41.555 (5)O1—C311.201 (5)
C13—C121.331 (5)C26—H26A0.9600
C13—C141.518 (5)C26—H26B0.9600
C10—C11.557 (4)C26—H26C0.9600
C10—C251.544 (5)C24—H24A0.9600
C11—C121.474 (5)C24—H24B0.9600
C11—O51.230 (4)C24—H24C0.9600
C7—H7A0.9700C25—H25A0.9600
C7—H7B0.9700C25—H25B0.9600
C7—C61.507 (5)C25—H25C0.9600
C7—C81.546 (5)C20—H200.9800
C3—H30.9800C20—C211.516 (7)
C3—C41.537 (5)C20—C301.508 (6)
C3—C21.520 (6)C22—H22A0.9700
C6—H6A0.9700C22—H22B0.9700
C6—H6B0.9700C22—C211.499 (7)
C12—H120.9300C31—C321.473 (6)
C4—C231.546 (6)C32—H32A0.9600
C4—C241.543 (5)C32—H32B0.9600
O4—H40.8200C32—H32C0.9600
O4—C231.328 (5)C29—H29A0.9600
C1—H1A0.9700C29—H29B0.9600
C1—H1B0.9700C29—H29C0.9600
C1—C21.521 (5)C21—H21A0.9700
C16—H16A0.9700C21—H21B0.9700
C16—H16B0.9700C28—H28A0.9600
C16—C151.538 (5)C28—H28B0.9600
C16—C171.539 (6)C28—H28C0.9600
C8—C141.594 (5)C30—H30A0.9600
C8—C261.559 (5)C30—H30B0.9600
C2—H2A0.9700C30—H30C0.9600
C2—H2B0.9700
C13—C18—H18106.0C20—C19—C18112.3 (3)
C13—C18—C19112.4 (3)C20—C19—H19107.5
C13—C18—C17111.2 (3)C29—C19—C18111.6 (3)
C19—C18—H18106.0C29—C19—H19107.5
C17—C18—H18106.0C29—C19—C20110.2 (3)
C17—C18—C19114.3 (3)C13—C14—C8109.5 (3)
C31—O2—C3118.1 (3)C13—C14—C15112.8 (3)
C10—C9—H9104.1C13—C14—C27106.6 (3)
C11—C9—H9104.1C15—C14—C8109.6 (3)
C11—C9—C10116.8 (3)C15—C14—C27106.1 (3)
C11—C9—C8107.6 (3)C27—C14—C8112.2 (3)
C8—C9—H9104.1C18—C17—C22110.0 (3)
C8—C9—C10118.2 (3)C16—C17—C18108.3 (3)
C10—C5—H5104.4C16—C17—C22109.5 (4)
C10—C5—C4115.5 (3)C28—C17—C18109.4 (4)
C6—C5—H5104.4C28—C17—C16110.1 (4)
C6—C5—C10111.1 (3)C28—C17—C22109.5 (4)
C6—C5—C4115.4 (3)C14—C27—H27A109.5
C4—C5—H5104.4C14—C27—H27B109.5
C12—C13—C18120.3 (3)C14—C27—H27C109.5
C12—C13—C14119.7 (3)H27A—C27—H27B109.5
C14—C13—C18119.9 (3)H27A—C27—H27C109.5
C5—C10—C9108.0 (3)H27B—C27—H27C109.5
C5—C10—C1107.7 (3)O4—C23—C4111.3 (4)
C1—C10—C9107.2 (3)O3—C23—C4124.7 (4)
C25—C10—C9112.3 (3)O3—C23—O4123.9 (4)
C25—C10—C5112.6 (3)C8—C26—H26A109.5
C25—C10—C1108.7 (3)C8—C26—H26B109.5
C12—C11—C9117.4 (3)C8—C26—H26C109.5
O5—C11—C9124.0 (4)H26A—C26—H26B109.5
O5—C11—C12118.6 (4)H26A—C26—H26C109.5
H7A—C7—H7B107.6H26B—C26—H26C109.5
C6—C7—H7A108.7C4—C24—H24A109.5
C6—C7—H7B108.7C4—C24—H24B109.5
C6—C7—C8114.1 (3)C4—C24—H24C109.5
C8—C7—H7A108.7H24A—C24—H24B109.5
C8—C7—H7B108.7H24A—C24—H24C109.5
O2—C3—H3109.9H24B—C24—H24C109.5
O2—C3—C4105.2 (3)C10—C25—H25A109.5
O2—C3—C2107.8 (3)C10—C25—H25B109.5
C4—C3—H3109.9C10—C25—H25C109.5
C2—C3—H3109.9H25A—C25—H25B109.5
C2—C3—C4114.0 (3)H25A—C25—H25C109.5
C5—C6—H6A109.5H25B—C25—H25C109.5
C5—C6—H6B109.5C19—C20—H20107.7
C7—C6—C5110.6 (3)C21—C20—C19110.3 (4)
C7—C6—H6A109.5C21—C20—H20107.7
C7—C6—H6B109.5C30—C20—C19112.3 (4)
H6A—C6—H6B108.1C30—C20—H20107.7
C13—C12—C11124.9 (3)C30—C20—C21111.0 (4)
C13—C12—H12117.6C17—C22—H22A108.4
C11—C12—H12117.6C17—C22—H22B108.4
C3—C4—C5110.1 (3)H22A—C22—H22B107.5
C3—C4—C23106.5 (3)C21—C22—C17115.5 (4)
C3—C4—C24108.5 (3)C21—C22—H22A108.4
C23—C4—C5115.6 (3)C21—C22—H22B108.4
C24—C4—C5111.1 (3)O2—C31—C32112.7 (4)
C24—C4—C23104.7 (3)O1—C31—O2122.0 (4)
C23—O4—H4109.5O1—C31—C32125.3 (4)
C10—C1—H1A109.1C31—C32—H32A109.5
C10—C1—H1B109.1C31—C32—H32B109.5
H1A—C1—H1B107.9C31—C32—H32C109.5
C2—C1—C10112.4 (3)H32A—C32—H32B109.5
C2—C1—H1A109.1H32A—C32—H32C109.5
C2—C1—H1B109.1H32B—C32—H32C109.5
H16A—C16—H16B107.8C19—C29—H29A109.5
C15—C16—H16A109.0C19—C29—H29B109.5
C15—C16—H16B109.0C19—C29—H29C109.5
C15—C16—C17112.8 (4)H29A—C29—H29B109.5
C17—C16—H16A109.0H29A—C29—H29C109.5
C17—C16—H16B109.0H29B—C29—H29C109.5
C9—C8—C14107.6 (2)C20—C21—H21A109.2
C9—C8—C26109.4 (3)C20—C21—H21B109.2
C7—C8—C9110.5 (3)C22—C21—C20112.1 (4)
C7—C8—C14110.6 (3)C22—C21—H21A109.2
C7—C8—C26107.3 (3)C22—C21—H21B109.2
C26—C8—C14111.6 (3)H21A—C21—H21B107.9
C3—C2—C1113.3 (3)C17—C28—H28A109.5
C3—C2—H2A108.9C17—C28—H28B109.5
C3—C2—H2B108.9C17—C28—H28C109.5
C1—C2—H2A108.9H28A—C28—H28B109.5
C1—C2—H2B108.9H28A—C28—H28C109.5
H2A—C2—H2B107.7H28B—C28—H28C109.5
C16—C15—H15A108.8C20—C30—H30A109.5
C16—C15—H15B108.8C20—C30—H30B109.5
C16—C15—C14113.7 (3)C20—C30—H30C109.5
H15A—C15—H15B107.7H30A—C30—H30B109.5
C14—C15—H15A108.8H30A—C30—H30C109.5
C14—C15—H15B108.8H30B—C30—H30C109.5
C18—C19—H19107.5
C18—C13—C12—C11172.7 (3)C6—C7—C8—C9−46.1 (4)
C18—C13—C14—C8157.9 (3)C6—C7—C8—C14−165.0 (3)
C18—C13—C14—C1535.6 (4)C6—C7—C8—C2673.1 (4)
C18—C13—C14—C27−80.4 (4)C12—C13—C14—C8−25.8 (4)
C18—C19—C20—C2152.9 (5)C12—C13—C14—C15−148.1 (3)
C18—C19—C20—C30177.2 (4)C12—C13—C14—C2795.9 (4)
C18—C17—C22—C21−49.9 (6)C4—C5—C10—C9−170.3 (3)
O2—C3—C4—C570.1 (4)C4—C5—C10—C1−54.8 (4)
O2—C3—C4—C23−163.9 (3)C4—C5—C10—C2565.0 (4)
O2—C3—C4—C24−51.7 (4)C4—C5—C6—C7162.7 (3)
O2—C3—C2—C1−65.0 (4)C4—C3—C2—C151.4 (4)
C9—C10—C1—C2171.1 (3)C16—C15—C14—C13−38.0 (5)
C9—C11—C12—C13−1.0 (5)C16—C15—C14—C8−160.3 (3)
C9—C8—C14—C1358.6 (3)C16—C15—C14—C2778.4 (4)
C9—C8—C14—C15−177.2 (3)C16—C17—C22—C2169.0 (5)
C9—C8—C14—C27−59.6 (3)O5—C11—C12—C13−179.0 (3)
C5—C10—C1—C255.1 (4)C8—C9—C10—C5−47.2 (4)
C5—C4—C23—O4−55.8 (5)C8—C9—C10—C1−163.0 (3)
C5—C4—C23—O3127.1 (5)C8—C9—C10—C2577.6 (4)
C13—C18—C19—C20−177.8 (3)C8—C9—C11—C1234.8 (4)
C13—C18—C19—C2957.9 (4)C8—C9—C11—O5−147.3 (3)
C13—C18—C17—C1655.1 (4)C8—C7—C6—C558.0 (4)
C13—C18—C17—C22174.8 (4)C2—C3—C4—C5−47.8 (4)
C13—C18—C17—C28−64.9 (4)C2—C3—C4—C2378.3 (4)
C10—C9—C11—C12170.5 (3)C2—C3—C4—C24−169.6 (3)
C10—C9—C11—O5−11.6 (5)C15—C16—C17—C18−61.3 (5)
C10—C9—C8—C742.1 (4)C15—C16—C17—C22178.7 (3)
C10—C9—C8—C14162.9 (3)C15—C16—C17—C2858.3 (5)
C10—C9—C8—C26−75.8 (4)C19—C18—C13—C12−91.8 (4)
C10—C5—C6—C7−63.3 (4)C19—C18—C13—C1484.5 (4)
C10—C5—C4—C351.6 (4)C19—C18—C17—C16−73.6 (4)
C10—C5—C4—C23−69.1 (4)C19—C18—C17—C2246.1 (5)
C10—C5—C4—C24171.8 (3)C19—C18—C17—C28166.4 (4)
C10—C1—C2—C3−55.2 (4)C19—C20—C21—C22−55.9 (5)
C11—C9—C10—C5−178.2 (3)C14—C13—C12—C11−3.6 (5)
C11—C9—C10—C166.0 (4)C17—C18—C13—C12138.5 (4)
C11—C9—C10—C25−53.4 (4)C17—C18—C13—C14−45.2 (4)
C11—C9—C8—C7177.0 (3)C17—C18—C19—C20−49.7 (5)
C11—C9—C8—C14−62.2 (3)C17—C18—C19—C29−174.1 (4)
C11—C9—C8—C2659.2 (4)C17—C16—C15—C1453.2 (5)
C7—C8—C14—C13179.3 (3)C17—C22—C21—C2056.2 (6)
C7—C8—C14—C15−56.4 (4)C26—C8—C14—C13−61.4 (3)
C7—C8—C14—C2761.1 (3)C26—C8—C14—C1562.8 (4)
C3—O2—C31—O16.8 (6)C26—C8—C14—C27−179.6 (3)
C3—O2—C31—C32−174.7 (3)C24—C4—C23—O466.8 (4)
C3—C4—C23—O4−178.4 (4)C24—C4—C23—O3−110.4 (5)
C3—C4—C23—O34.4 (6)C25—C10—C1—C2−67.2 (4)
C6—C5—C10—C955.8 (3)C31—O2—C3—C4149.8 (3)
C6—C5—C10—C1171.3 (3)C31—O2—C3—C2−88.2 (4)
C6—C5—C10—C25−68.9 (4)C29—C19—C20—C21178.0 (4)
C6—C5—C4—C3−176.5 (3)C29—C19—C20—C30−57.7 (5)
C6—C5—C4—C2362.8 (4)C28—C17—C22—C21−170.1 (5)
C6—C5—C4—C24−56.3 (4)C30—C20—C21—C22179.0 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4···O1i0.821.912.695 (4)161
C1—H1A···O50.972.393.023 (5)122
C25—H25C···O50.962.383.058 (5)127
C30—H30B···O1ii0.962.603.468 (6)151
C32—H32C···O3iii0.962.523.445 (6)162
Symmetry codes: (i) −x+3/2, y−1/2, −z+3; (ii) x, y, z−1; (iii) x−1/2, −y+1/2, −z+3.
 

Acknowledgements

The author(s) express their sincere gratitude to Ms Tahira H. S., Chief of Research and Development at Green Space Herbs, for her valuable guidance, insightful discussions, and continuous support throughout the course of this work. The author(s) also appreciate the resources and facilities provided by Green Space Herbs.

References

Return to citationAl-Harrasi, A., Rehman, N. U., Khan, A. L., Al-Broumi, M., Al-Amri, I., Hussain, J., Hussain, H. & Csuk, R. (2018). PLoS One 13, e0198666.  PubMed Google Scholar
 Return to citationDolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 Return to citationGroom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179.  Web of Science CrossRef IUCr Journals Google Scholar
 Return to citationGupta, M., Kumar, S., Kumar, R., Kumar, A., Verma, R., Darokar, M. P., Rout, P. & Pal, A. (2021). Biomed. Pharmacother. 144, 112302.  CrossRef PubMed Google Scholar
 Return to citationIto, M., Misao, K., Suzuki, H. & Noguchi, S. (2025a). Chem. Pharm. Bull. 73, 314–317.  CrossRef CAS Google Scholar
 Return to citationIto, M., Misao, K., Suzuki, H. & Noguchi, S. (2025b). Chem. Pharm. Bull. (Tokyo) 73, 314–317.  CrossRef CAS PubMed Google Scholar
 Return to citationKhaafi, F. & Javadi, B. (2023). Mini Rev. Med. Chem. 23, 1912–1925.  CrossRef CAS PubMed Google Scholar
 Return to citationLauss, J., Kappacher, C., Isser, O., Huck, C. W. & Rainer, M. (2024). Spectrochim. Acta A Mol. Biomol. Spectrosc. 316, 124384.  PubMed Google Scholar
 Return to citationLi, C., He, Q., Xu, Y., Lou, H. & Fan, P. (2022). ACS Omega 7, 9853–9866.  CrossRef CAS PubMed Google Scholar
 Return to citationLindner, S., Keim, S., Haddadzadegan, S., Fernandez Romero, O., Zöller, K., Stern, G., Cesi, I., Kafedjiiski, K. & Bernkop–Schnürch, A. (2026). Adv. Healthc. Mater. 15, e03721.  CrossRef PubMed Google Scholar
 Return to citationMajeed, A., Majeed, S., Satish, G., Manjunatha, R., Rabbani, S. N., Patil, N. V. P. & Mundkur, L. (2024). Front. Pharmacol. 15, 1428440.  CrossRef PubMed Google Scholar
 Return to citationPark, Y. S., Lee, J. H., Bondar, J., Harwalkar, J. A., Safayhi, H. & Golubic, M. (2002). Planta Med. 68, 397–401.  CrossRef PubMed CAS Google Scholar
 Return to citationParsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249–259.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 Return to citationRigaku OD (2024). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.  Google Scholar
 Return to citationSailer, E. R., Subramanian, L. R., Rall, B., Hoernlein, R. F., Ammon, H. P. & Safayhi, H. (1996). Br. J. Pharmacol. 117, 615–618.  CrossRef CAS PubMed Google Scholar
 Return to citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 Return to citationSheldrick, G. M. (2015). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
 Return to citationShen, S., Xu, X., Liu, Z., Liu, J. & Hu, L. (2015). Bioorg. Med. Chem. 23, 1982–1993.  CrossRef CAS PubMed Google Scholar
 Return to citationTeng, W., Zhou, Z., Cao, J. & Guo, Q. (2024). Foods 13, 2226.  CrossRef PubMed Google Scholar
 Return to citationTsai, Y.-C., Chang, H.-H., Chou, S.-C., Chu, T. W., Hsu, Y.-J., Hsiao, C.-Y., Lo, Y.-H., Wu, N.-L., Chang, D.-C. & Hung, C.-F. (2022). Int. J. Mol. Sci. 23, 9863.  CrossRef PubMed Google Scholar

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ISSN: 2056-9890
Volume 82| Part 6| June 2026| Pages 738-742
https://doi.org/10.1107/S2056989026005360
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