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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 82| Part 10| October 2026|
https://doi.org/10.1107/S2056989026009205

Synthesis and crystal structure of N-benzyl-5,6-ep­­oxy-7-oxabi­cyclo­[2.2.1]heptane-2,3-dicarboximide

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Joseph F. DeJesus,a Mary Helene Marmande,b Bailey N. Baxter,b Masakazu Nambo,a Cathleen M. Cruddena,c and David C. Forbesb*

aInstitute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University, Nagoya 464-8601, Japan, bUniversity of South Alabama, Department of Chemistry, 6040 USA Drive South, Mobile, Alabama 36688, USA, and cQueen's University, Kingston, Ontario K7L 3N6, Canada
*Correspondence e-mail: [email protected]

Edited by D. R. Manke, University of Massachusetts Dartmouth, USA (Received 10 August 2026; accepted 2 September 2026; online 8 September 2026)

The title compound, C15H13NO4, is an analog of a well-known cytotoxic mol­ecule, canthardin. The compound possesses a 3/5/5/5 contiguous stereo-defined ring network, which features cyclic furan, oxirane and cyclic carboxamide moieties. The flexibility of the N-benzyl unit allows for supra­molecular chiral (but racemic) packing in the extended crystal structure. The inter­molecular inter­actions in the crystal are dominated by H⋯H and O⋯H van der Waals inter­actions, as shown by Hirshfeld analysis.

CCDC reference: 2585299

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1. Chemical context

Compounds based on the 7-oxabi­cyclo­[2.2.1]heptane motif have attracted considerable attention in medicinal chemistry because their conformationally constrained structures can effectively mimic biologically relevant architectures (Scott et al., 2026View full citation). This framework is closely related to those present in norcantharidin, a system whose methyl­ated cousin cantharidin has been investigated for anti­cancer, enzyme-inhibitory, and agrochemical applications (Lawley et al., 2026View full citation). Norcanthardin derivatives also possess the advantage of simplicity and scalability of synthesis, for example, by a very straightforward Diels-Alder cyclization (Fig. 1[link], formation of 1). In our hands, compound 1 can be isolated in 76% yield in gram qu­anti­ties by this route, with exclusive exo selectivity (Hill et al., 2022View full citation). In the 7-oxabi­cyclo­[2.2.1]hept-5-ene core, there is a convenient point of unsaturation to allow for further derivatization (Alves et al., 2023View full citation). Using 1 as a common synthon, we were inter­ested in developing new analogs of norcanthardin to study their biological effects.

[Figure 1]
Figure 1
(A) Synthesis of alkene synthon of 7-oxabi­cyclo­[2.2.1]hept-5-ene core (1) and transformation of anhydride moiety into more stable 2,3-dicarboximide group (3). (B) Transformation of 3 to 4 using mCPBA oxidation, and its three-dimensional arrangement with conserved stereochemical control.

This report details the formation and crystallization of the new norcanthardin analog N-benzyl-5,6-ep­oxy-7-oxabi­cyclo­[2.2.1]heptane-2,3-dicarboximide (4). Fig. 1[link]A details the route, which includes nucleophilic ring opening of the anhydride moiety of 1 with benzyl amine to form amidic acid 2, in 91% yield, and subsequent closing to form the phthalimide 3 with carbodi­imide chemistry (79% yield). Compound 3 is a norcanthardin analog with a 5/5/5 tricyclic rigid core and an alkene synthetic handle. Formation of an oxirane moiety through the use of mCPBA oxidation chemistry (Fig. 1[link]B) resulted in formation of the highly rigid 3/5/5/5 tetra­cyclic norcanthardin derivative 4 in 97% yield.

[Scheme 1]

The symmetry of the 3/5/5/5 tetra­cyclic core and the use of an oxirane functionality in 4 represents both a valuable synthetic inter­mediate and a versatile platform for further development of biologically active mol­ecules. Furthermore, the rigid scaffold also imposes a well-defined three-dimensional arrangement of functional groups, making this synthon an attractive system for studies of structure–activity relationships and mol­ecular recognition. As such, we sought to characterize the solid-state properties of 4 through X-ray crystallography as an initial attempt to probe structural properties of this new analog.

2. Structural commentary

Compound 4 was crystallized by vapor diffusion of hexa­nes into a 1.5 mL tube of 4 dissolved in ethyl acetate. Large colorless block-like crystals grew on the sides of the wall of the glass tube. After mounting one of these crystals, the mol­ecular structure of 4 was obtained as shown in Fig. 2[link]. The asymmetric unit of 4 crystallizes in the ortho­rhom­bic Pca21 space group, and has two crystallographically distinct mol­ecules, 4 and 4A, with no co-crystallized solvent mol­ecules observed. In the course of refining the structure, we found that the absolute configuration of the structure could not be determined reliably. After conducting a Bijovet pairs analysis, we found that the crystal had a 70.1% chance to be an inversion twin. As a result, the crystal was refined as an inversion twin to remedy this issue for further analysis. The rationale for formation of an inversion twin became apparent upon observing the extended crystal structure (vide infra, Fig. 4).

[Figure 2]
Figure 2
Observed asymmetric unit of 4, with co-crystallized mol­ecule 4A. Atom labels for each fragment are shown. Displacement ellipsoids of gray, blue and red correspond to carbon, nitro­gen and oxygen, respectively. White spheres correspond to hydrogen atoms.

Overlaying both mol­ecules in the asymmetric unit (Fig. 3[link]), demonstrates that each fragment is nearly identical, with an alignment RMSD of 0.129 Å. Of note, both fragments have the same contiguous absolute confirguration in the chiral centers (C1/C1A = S, C2/C2A = R, C3/C3A = S, C4/C4A = R, C5/C5A = S, C6/C6A = R), demonstrating that there was no erosion of the starting chirality in the formation of the oxirane unit, or during any of the prior chemical transformations. This results in all four rings of the tetra­cyclic core ‘puckering up', and allowing the oxygen heteroatoms to orient themselves in one direction, which is critical in the cytotoxicity of this family of compounds (Chattopadhyay et al., 2016View full citation). Additionally, the 1H NMR spectrum implies that there is only one single stereoisomer present in the bulk of the isolated compound (see Section 5, preparation of 4).

[Figure 3]
Figure 3
Overlayed mol­ecules in asymmetric unit, 4 and 4A. Both mol­ecules in the asymmetric unit are nearly identical. Probability ellipsoids shown at 50%.

3. Supra­molecular features

Fig. 4[link] shows the supra­molecular packing of 4 and 4A down the a and b axes. Implied by the Pca21 space group, the supra­molecular structure shows the two glide-plane operations, where the mol­ecules propagate in a twisting fashion across the crystal. On the edges of the diagram in Fig. 4[link] left, the N-benzyl units are oriented in opposite directions. This alternating orientation of the N-benzyl units is shown in both views in Fig. 4[link] as an apparent packing in the crystal. These alternating N-benzyl units explain the two crystallographically distinct mol­ecules in the asymmetric unit, despite the individual mol­ecules being chemically identical when overlain (Fig. 3[link]), since they possess different orientations in the expanded crystal. Because this propagation has a chiral operation, the crystal of 4 crystallizes as a racemic twin due to the presence of the opposite orientation co-crystallizing with this mol­ecule.

[Figure 4]
Figure 4
Supra­molecular packing of 4, in a completed unit cell. Left: view of the supra­molecular packing looking down the a axis. Right: view of the supra­molecular packing looking down the b axis. Displacement ellipsoids are shown at 50% probability.

Further analyzing the surface contacts in the expanded crystal provides no evidence of classical hydrogen bonding that would explain the inter­molecular inter­actions. We conducted both a two- and a three-dimensional Hirshfeld analysis to probe the types of other inter­molecular inter­actions (such as Van der Waals) within the crystal of 4, with details summarized in Table 1[link], Fig. 5[link] and Fig. 6[link]. The majority of the surface atom contacts were assigned to H⋯O atoms (43.3%), H.·H atoms (39.6%) and H⋯C atoms (14.8%) as shown in Table 1[link] and two-dimensional Hirshfeld plots in Fig. 4[link]. This is further shown by the three-dimensional Hirshfeld view, where the strongest indication of surface inter­actions (in red) is positioned around the epoxide and furan oxygen atoms, and the axial H atoms in the tetra­cyclic core.

Table 1
Listed surface atom contacts and their percentage contribution to total contacts

Atom contact Contribution (%)
H⋯O/O⋯H 43.3
H⋯H 39.6
H⋯C/C⋯H 14.8
H⋯N/N⋯H 1.1
O⋯O 0.7
C⋯O/O⋯C 0.6
[Figure 5]
Figure 5
Two-dimensional Hirshfeld Plots of all surface contacts (A) and of the greatest atomic contact contributors of (B) H⋯O/O⋯H contacts, (C) H⋯H contacts and (D) H⋯C contacts. The brighter blue color shows greater abundance of surface inter­actions.
[Figure 6]
Figure 6
Three-dimensional Hirshfeld surface of the asymmetric unit of 4, plotted over dnorm in the range −0.2533 to 1.3970 a.u. The darker red spheres show the greatest amount of inter­molecular surface inter­actions for specific atoms.

4. Database survey

A database survey (CSD, July 2026; Groom et al., 2016View full citation) with the tetra­cyclic core and the corresponding stereochemistry observed in 4 revealed only one other structure (Ren et al. 2026View full citation, CCDC: 2486893), with an N-3,5-di­chloro­phenyl substituent rather than an N-benzyl substituent in 4.

5. Synthesis and crystallization

All reactions were conducted under air in ambient conditions unless otherwise stated. All solvents were reagent grade and used as received. 1H and 13C{1H} NMR were conducted on a JEOL ECA-II 400 MHz and JEOL ECA-II 600 MHz spectrometers. All 1H and 13C{1H} NMR spectra were referenced to the residual solvent signal of CDCl3 at 7.26 and 77.16 ppm, respectively. IR spectra were obtained from a JASCO FT/IR-6600 spectrometer using the neat solid compounds. Melting point temperatures were collected on an OptiMelt MPA100 melting point apparatus.

7-Oxabi­cyclo­[2.2.1]hept-5-ene-2,3-di­carb­oxy­lic anhydride (1)

To a 100 mL round-bottomed flask (RBF) equipped with a septum and stir bar and containing maleic anhydride (8.0 g, 81.6 mmol, 3 equiv.) was added 40 mL cyclo­pentyl methyl ether (CPME). The mixture was externally warmed (318 K) until a solution was formed. After the solution was allowed to cool to room temperature, furan (2.0 mL, 27.5 mmol, 1 equiv.) was added by syringe. The sealed reaction mixture was allowed to stir at room temperature for 3 d at which time, the solid was collected by vacuum filtration and rinsed with diethyl ether (40 mL). Obtained after filtration was a white crystalline solid in 3.5 g (76% yield) and used without further purification. 1H NMR (400 MHz, CDCl3); 6.58 (s, 2H, =CH), 5.47 (s, 2H, –CHO–), 3.18 (s, 2H, CH).

3-(Benzyl­carbamo­yl)-5,6-di­hydro-7-oxabi­cyclo­[2.2.1]heptane-2-carb­oxy­lic acid (2)

7-Oxabi­cyclo­[2.2.1]hept-5-ene-2,3-di­carb­oxy­lic anhydride (1) (1.5 g, 8.9 mmol, 1.0 equiv.) was added to a 100 mL RBF equipped with a magnetic stir bar and septum. Di­chloro­methane (40 mL) was next added to the RBF at room temperature and placed under a blanket of argon. Benzyl­amine (1.0 mL, 9.4 mmol, 1.05 equiv.) was dissolved in di­chloro­methane (5 mL) and as a solution, added to the RBF using a disposable Pasteur pipet. The resulting mixture which began forming a precipitant within 5 min of adding the amine was allowed to stir overnight while maintaining the blanket of argon. After adding diethyl ether (20 mL) to the reaction mixture and allowing the slurry to stir for approximately 10 min at room temperature, the solid was isolated by filtration and rinsing with diethyl ether (50 mL). Obtained after filtration was a white crystalline solid in 2.2 g (91% yield) and used without further purification. 1H NMR (400 MHz, CDCl3); 7.32–7.31 (m, 5H), 6.79 (br s, 1H), 6.48 (d, J = 5.2 Hz, 1H), 6.40 (d, J = 4.8 Hz, 1H), 5.33 (s, 1H), 5.08 (s, 1H), 4.43 (dd, J = 14.0, 6.0 Hz, 1H), 4.31 (dd, J = 14.0, 5.2 Hz, 1H), 2.90 (d, J = 9.2 Hz, 1H), 2.82 (d, J = 8.4 Hz, 1H).

N-Benzyl-5,6-di­hydro-7-oxabi­cyclo­[2.2.1]heptane-2,3-dicarboximide (3)

After the addition of 3-(benzyl­carbamo­yl)-5,6-di­hydro-7-oxabi­cyclo­[2.2.1]heptane-2-carb­oxy­lic acid (2) (139 mg, 0.51 mmol, 1.0 equiv.), di­chloro­methane (DCM) (4.5 mL), di­methyl­formamide (DMF) (0.50 mL), and 1-hy­droxy­benzotriazole (HOBt) (86 mg, 0.56 mmol, 1.1 equiv.) to a 10 mL RBF, the solution was externally cooled using an ice bath and placed under a blanket of Ar. A solution of di­cyclo­hexyl­carbodi­imide (DCC) (116 mg, 0.56 mmol, 1.1 equiv.) in 5 mL of DCM was added dropwise directly into the RBF by syringe. The reaction mixture was allowed to gradually warm to room temperature under a blanket of argon and stir overnight at which time the reaction mixture was filtered through a Celite pad as part of a disposable Pasteur pipet. After the pipet was rinsed with DCM (5 mL), the solution was concentrated in vacuo and purified by column chromatography (SiO2 (10 mm x 80 mm); gradient system EtOAc:hexa­nes 1:4 (50 mL), 1:2 (50 mL), 1:1 (50 mL); 10 mL fractions collecting tubes 5-14). The isolated material after removal of the volatiles in vacuo was 103 mg [0.40 mmol (79% yield using 3-(benzyl­carbamo­yl)-5,6-di­hydro-7-oxabi­cyclo­[2.2.1]heptane-2-carb­oxy­lic acid (2) as limiting reactant)]; white solid; 1H NMR (400 MHz, CDCl3); 7.32–7.31 (m, 5H), 6.52 (s, 2H), 5.30 (s, 2H), 4.65 (s, 2H), 2.87 (s, 2H).

N-Benzyl-5,6-ep­oxy-7-oxabi­cyclo­[2.2.1]heptane-2,3-dicarb­oximide (4)

After the addition of N-benzyl-5,6-di­hydro-7-oxabi­cyclo­[2.2.1]heptane-2,3-dicarboximide (3) (266 mg, 1.04 mmol, 1.0 equiv.) and di­chloro­methane (DCM) (2 mL) to a 30 mL (RBF), the solution was externally cooled using an ice bath and placed under a blanket of Ar. A suspension of m-chloro­perbenzoic acid (mCPBA) (359 mg, 2.08 mmol, 2.0 equiv.) in 3 mL of DCM was added after approximately five minutes dropwise directly into the RBF using a disposable Pasteur pipet. [Note: The actual amount weighed was 553 mg factoring the 65% purity.] The vial which contained the mCPBA was rinsed and transferred to the RBF using approximately 0.5 mL of DCM. The reaction mixture was allowed to gradually warm to room temperature under a blanket of Ar and stir overnight at which time the excess oxidant was quenched upon addition of a saturated aqueous solution of sodium sulfite (5 mL). After stirring at room temperature for 10 min, the organic phase was washed multiple times to remove 3-chloro­benzoic acid as the reaction was found to go to completion when working with 2.0 equiv. mCPBA using a saturated aqueous solution of sodium bicarbonate (3 × 5 mL). The organic layer was next washed with brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo. To obtain analytically pure material, the material was chromatographed (SiO2 (40 mm × 90 mm); gradient system EtOAc:hexa­nes 1:1 (100 mL), 2:1 (100 mL), 4:1 (200 mL); 20 mL fractions collecting tubes 9–18). The isolated material after removal of the volatiles in vacuo was 275 mg [1.0 mmol (97% yield using N-benzyl-5,6-di­hydro-7-oxabi­cyclo­[2.2.1]heptane-2,3-dicarboximide (3) as limiting reactant)]; white solid; m.p. 462–463 K. IR (neat, ATR) cm−1: 2968 (w), 1773 (w), 1955 (s), 1395 (m), 1175 (s), 1016 (s), 859 (s), 741 (s), 695 (s), 585 (s).

1H NMR (CDCl3, 600 MHz): δ 7.30–7.26 (m, 5H), 4.84 (s, 2H), 4.64 (s, 2H), 3.50 (s, 2H), 2.99 (s, 2H). 13C{1H} NMR (CDCl3, 150 MHz): d 175.1, 135.1, 128.7, 128.1, 127.9, 76.7, 49.7, 47.9, 42.8. TLC: Silica gel 60 F254 (2:1 ethyl acetate/hexa­nes); Rf = 0.3.

Crystallization and mounting of 4

After dissolving 59 mg of 4 in 1.1 mL of ethyl acetate, 0.4 mL of the solution were placed into a 1.5 mL tube. The tube was then carefully placed into a 20 mL screw-capped vial charged with approximately 6 mL hexa­nes. After sealing the setup, large colorless block-like and plate crystals formed after 24 h. Crystals were taken directly from mother liquor using a spatula with paratone oil, and dispersed into more paratone oil. The crystal was put on a mounting loop, put on the goniometer head and frozen under a stream of LN2 (143 K) while data collection was conducted.

6. Refinement

Crystal data collection and structure refinement details are shown and summarized in Table 2[link]. The crystal data was refined as a two-component inversion twin (twin law: [−1, 0, 0, 0, −1, 0, 0, 0, −1]). Due to poor agreement of observed values to calculated values, 5 reflections (1 1 Mathematical equation, 0 2 Mathematical equation, 1 2 2, 2 5 Mathematical equation, 4 4 1) were omitted in the refinement. H atoms were attached to their parent atoms geometrically and constrained to ride on their parent atoms.

Table 2
Experimental details

Crystal data
Chemical formula C15H13NO4
Mr 271.26
Crystal system, space group Orthorhombic, Pca21
Temperature (K) 143
a, b, c (Å) 11.078 (5), 11.988 (5), 18.432 (8)
V (Å3) 2447.9 (19)
Z 8
Radiation type Mo Kα
μ (mm−1) 0.11
Crystal size (mm) 0.31 × 0.20 × 0.14
 
Data collection
Diffractometer Rigaku Pilatus 200K
Absorption correction Numerical (Busing et al., 1957View full citation; Coppens et al., 1965View full citation)
Tmin, Tmax 0.985, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections 37607, 5347, 4234
Rint 0.044
(sin θ/λ)max (Å−1) 0.649
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.077, 0.92
No. of reflections 5347
No. of parameters 362
No. of restraints 1
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.25, −0.18
Absolute structure Refined as an inversion twin
Computer programs: CrystalClear-SM Expert (Rigaku, 2016View full citation), SHELXT (Sheldrick, 2015aView full citation), SHELXL2019/2 (Sheldrick 2015bView full citation), ShelXle (Hübschle et al., 2011View full citation), OLEX2 (Dolomanov et al., 2009View full citation) and CrystalExplorer (Spackman et al., 2021View full citation).

Supporting information

CCDC reference: 2585299

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989026009205/yy2025sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989026009205/yy2025Isup2.hkl

checkCIF report


Computing details top

N-Benzyl-5,6-epoxy-7-oxabicyclo[2.2.1]heptane-2,3-dicarboximide top
Crystal data top
C15H13NO4Dx = 1.472 Mg m−3
Mr = 271.26Mo Kα radiation, λ = 0.71075 Å
Orthorhombic, Pca21Cell parameters from 3248 reflections
a = 11.078 (5) Åθ = 3.3–27.5°
b = 11.988 (5) ŵ = 0.11 mm−1
c = 18.432 (8) ÅT = 143 K
V = 2447.9 (19) Å3Block-like, colorless
Z = 80.31 × 0.20 × 0.14 mm
F(000) = 1136
Data collection top
Rigaku Pilatus 200K
diffractometer		4234 reflections with I > 2σ(I)
Radiation source: Rotating AnodeRint = 0.044
profile data from ω–scansθmax = 27.5°, θmin = 3.3°
Absorption correction: numerical
(Busing et al., 1957; Coppens et al., 1965)		h = −14→14
Tmin = 0.985, Tmax = 0.991k = −15→11
37607 measured reflectionsl = −23→23
5347 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.077 w = 1/[σ2(Fo2) + (0.0499P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.92(Δ/σ)max < 0.001
5347 reflectionsΔρmax = 0.25 e Å−3
362 parametersΔρmin = −0.17 e Å−3
1 restraintAbsolute structure: Refined as an inversion twin
Primary atom site location: dual
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. Refined as a 2-component inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O1−0.11945 (18)0.50167 (16)0.64782 (12)0.0307 (5)
O2−0.06787 (16)0.49189 (14)0.51523 (11)0.0192 (4)
O1A0.13975 (17)1.02313 (17)0.34982 (11)0.0303 (5)
O30.22361 (16)0.36364 (15)0.43955 (10)0.0289 (4)
O2A0.18982 (15)1.02605 (14)0.48285 (9)0.0199 (4)
O40.07162 (16)0.70987 (14)0.40423 (9)0.0260 (4)
O3A0.48025 (15)1.12960 (14)0.56683 (10)0.0262 (4)
O4A0.32226 (16)0.78153 (15)0.58545 (10)0.0278 (4)
N10.16171 (19)0.53901 (17)0.40756 (12)0.0206 (5)
N1A0.40913 (17)0.95429 (17)0.59153 (11)0.0194 (4)
C10.0028 (3)0.4713 (3)0.63137 (15)0.0309 (7)
H10.0605390.4509850.6709150.037*
C2−0.0374 (2)0.5851 (2)0.62233 (13)0.0248 (6)
H2−0.0080890.6456710.6552270.030*
C1A0.2652 (2)1.0441 (2)0.36676 (14)0.0281 (6)
H1A0.3250821.0616020.3277940.034*
C30.0226 (2)0.4313 (2)0.55475 (14)0.0232 (6)
H30.0213790.3484870.5480420.028*
C2A0.2146 (2)0.9333 (2)0.37433 (13)0.0236 (6)
H2A0.2386470.8715350.3408890.028*
C4−0.0389 (2)0.6008 (2)0.54095 (13)0.0186 (5)
H4−0.0923830.6619990.5229080.022*
C3A0.2857 (2)1.0810 (2)0.44490 (14)0.0221 (5)
H3A0.2912391.1633770.4525980.027*
C50.1396 (3)0.4906 (2)0.52978 (15)0.0212 (7)
H50.2050420.4860040.5670120.025*
C4A0.2109 (2)0.9161 (2)0.45570 (14)0.0190 (5)
H4A0.1526310.8581440.4728390.023*
C60.0943 (2)0.61035 (19)0.51891 (13)0.0187 (5)
H60.1397690.6661280.5485680.022*
C5A0.3964 (2)1.0131 (2)0.47013 (15)0.0172 (6)
H5A0.4645371.0162010.4346410.021*
C70.1816 (2)0.4530 (2)0.45617 (15)0.0209 (5)
C6A0.3429 (2)0.89612 (19)0.47726 (12)0.0173 (5)
H6A0.3837320.8410270.4447410.021*
C80.1057 (2)0.6304 (2)0.43823 (13)0.0195 (5)
C7A0.4354 (2)1.0435 (2)0.54662 (14)0.0203 (5)
C90.1925 (2)0.5348 (2)0.33081 (13)0.0278 (6)
H9A0.1189120.5486820.3017240.033*
H9B0.2221560.4590830.3187860.033*
C8A0.3552 (2)0.8660 (2)0.55583 (13)0.0190 (5)
C100.2880 (2)0.6195 (2)0.31034 (13)0.0209 (6)
C9A0.4347 (2)0.9512 (2)0.66915 (13)0.0251 (6)
H9AA0.3604860.9294160.6955500.030*
H9AB0.4579371.0267880.6856210.030*
C110.2762 (2)0.6842 (2)0.24819 (13)0.0230 (6)
H110.2086890.6741470.2171230.028*
C10A0.5341 (2)0.8706 (2)0.68755 (13)0.0217 (6)
C120.3623 (2)0.7627 (2)0.23165 (12)0.0240 (6)
H120.3532180.8070330.1892680.029*
C11A0.6367 (2)0.8630 (2)0.64473 (15)0.0325 (7)
H11A0.6439530.9081790.6026190.039*
C130.4613 (2)0.7782 (2)0.27534 (14)0.0250 (6)
H130.5196620.8335090.2637680.030*
C12A0.7284 (3)0.7901 (2)0.66289 (16)0.0373 (7)
H12A0.7981310.7852770.6330280.045*
C140.4751 (2)0.7121 (2)0.33665 (13)0.0257 (6)
H140.5440370.7212400.3667290.031*
C13A0.7196 (2)0.7244 (2)0.72402 (15)0.0296 (7)
H13A0.7827990.6742820.7363150.036*
C150.3898 (2)0.6336 (2)0.35402 (13)0.0248 (6)
H150.3999880.5886730.3960100.030*
C14A0.6184 (2)0.7320 (2)0.76712 (12)0.0255 (6)
H14A0.6122380.6875240.8096370.031*
C15A0.5263 (2)0.8034 (2)0.74899 (13)0.0219 (6)
H15A0.4563750.8070330.7787320.026*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0230 (10)0.0431 (13)0.0261 (11)−0.0020 (8)0.0078 (9)0.0068 (8)
O20.0153 (9)0.0201 (10)0.0223 (10)−0.0016 (7)−0.0032 (8)−0.0013 (7)
O1A0.0248 (11)0.0368 (11)0.0294 (12)0.0011 (9)−0.0088 (10)0.0067 (9)
O30.0239 (10)0.0221 (10)0.0408 (11)0.0029 (8)−0.0028 (8)−0.0060 (8)
O2A0.0144 (9)0.0215 (10)0.0238 (10)0.0039 (7)0.0005 (8)−0.0034 (7)
O40.0361 (10)0.0176 (10)0.0243 (9)−0.0017 (8)−0.0021 (8)0.0039 (7)
O3A0.0225 (9)0.0225 (10)0.0335 (10)−0.0046 (8)0.0003 (7)−0.0047 (8)
O4A0.0331 (10)0.0214 (10)0.0291 (10)−0.0024 (8)−0.0034 (8)0.0064 (8)
N10.0227 (11)0.0190 (12)0.0201 (11)−0.0023 (10)0.0026 (9)−0.0018 (9)
N1A0.0196 (11)0.0203 (12)0.0183 (11)0.0020 (10)−0.0011 (9)−0.0005 (9)
C10.0184 (13)0.051 (2)0.0235 (16)0.0057 (13)0.0007 (12)0.0142 (13)
C20.0180 (13)0.0338 (16)0.0227 (13)−0.0095 (12)0.0010 (10)−0.0020 (11)
C1A0.0213 (14)0.0369 (17)0.0261 (16)−0.0007 (13)−0.0019 (11)0.0088 (12)
C30.0209 (13)0.0184 (13)0.0304 (15)0.0000 (11)0.0035 (11)0.0079 (11)
C2A0.0222 (14)0.0314 (16)0.0173 (13)0.0045 (11)−0.0014 (10)−0.0011 (11)
C40.0184 (12)0.0165 (13)0.0208 (12)−0.0012 (10)−0.0024 (10)−0.0048 (9)
C3A0.0210 (13)0.0179 (13)0.0275 (14)−0.0051 (11)−0.0004 (11)0.0060 (11)
C50.0175 (15)0.0249 (15)0.0211 (16)0.0007 (10)−0.0036 (12)0.0030 (10)
C4A0.0183 (12)0.0176 (13)0.0211 (12)−0.0018 (10)−0.0018 (10)−0.0012 (10)
C60.0177 (12)0.0182 (14)0.0202 (12)−0.0039 (10)−0.0026 (10)0.0002 (10)
C5A0.0129 (13)0.0209 (14)0.0179 (15)0.0008 (10)0.0007 (12)0.0019 (10)
C70.0113 (11)0.0197 (15)0.0318 (14)−0.0027 (11)−0.0014 (11)0.0016 (11)
C6A0.0159 (12)0.0169 (13)0.0192 (12)0.0016 (10)0.0004 (10)−0.0041 (10)
C80.0187 (13)0.0182 (13)0.0217 (12)−0.0066 (11)−0.0018 (10)−0.0016 (10)
C7A0.0118 (11)0.0228 (15)0.0264 (13)0.0026 (11)0.0003 (10)−0.0047 (11)
C90.0336 (15)0.0322 (17)0.0176 (13)−0.0053 (13)0.0027 (11)−0.0065 (12)
C8A0.0163 (12)0.0179 (14)0.0230 (13)0.0051 (10)−0.0005 (10)−0.0002 (10)
C100.0215 (13)0.0220 (14)0.0192 (13)0.0003 (10)0.0041 (10)−0.0056 (10)
C9A0.0297 (15)0.0281 (16)0.0176 (13)0.0058 (13)−0.0043 (11)−0.0019 (11)
C110.0217 (13)0.0290 (15)0.0182 (13)0.0043 (12)0.0000 (11)−0.0049 (11)
C10A0.0220 (14)0.0248 (14)0.0182 (13)−0.0013 (11)−0.0037 (10)−0.0030 (10)
C120.0267 (14)0.0280 (16)0.0173 (15)0.0046 (12)0.0053 (12)0.0015 (11)
C11A0.0259 (14)0.0421 (18)0.0295 (14)0.0033 (13)0.0058 (12)0.0143 (13)
C130.0207 (14)0.0252 (15)0.0290 (15)0.0010 (12)0.0054 (11)0.0001 (11)
C12A0.0253 (15)0.0483 (19)0.0383 (17)0.0042 (14)0.0106 (12)0.0181 (15)
C140.0208 (12)0.0330 (15)0.0232 (13)0.0009 (12)−0.0006 (10)−0.0003 (11)
C13A0.0201 (14)0.0348 (17)0.0340 (16)0.0031 (12)−0.0027 (12)0.0079 (13)
C150.0270 (13)0.0281 (15)0.0195 (12)0.0031 (12)−0.0006 (10)0.0037 (11)
C14A0.0291 (15)0.0255 (16)0.0220 (15)−0.0054 (12)−0.0001 (12)0.0046 (11)
C15A0.0188 (12)0.0295 (15)0.0173 (13)−0.0035 (12)0.0008 (10)−0.0039 (11)
Geometric parameters (Å, º) top
O1—C21.431 (3)C4A—C6A1.534 (3)
O1—C11.435 (3)C4A—H4A1.0000
O2—C41.426 (3)C6—C81.512 (3)
O2—C31.436 (3)C6—H61.0000
O1A—C2A1.432 (3)C5A—C7A1.519 (4)
O1A—C1A1.446 (3)C5A—C6A1.528 (4)
O3—C71.207 (3)C5A—H5A1.0000
O2A—C4A1.429 (3)C6A—C8A1.499 (3)
O2A—C3A1.432 (3)C6A—H6A1.0000
O4—C81.201 (3)C9—C101.514 (3)
O3A—C7A1.204 (3)C9—H9A0.9900
O4A—C8A1.207 (3)C9—H9B0.9900
N1—C81.380 (3)C10—C111.389 (3)
N1—C71.384 (3)C10—C151.396 (3)
N1—C91.456 (3)C9A—C10A1.505 (3)
N1A—C8A1.382 (3)C9A—H9AA0.9900
N1A—C7A1.383 (3)C9A—H9AB0.9900
N1A—C9A1.459 (3)C11—C121.374 (4)
C1—C21.445 (4)C11—H110.9500
C1—C31.508 (4)C10A—C11A1.387 (4)
C1—H11.0000C10A—C15A1.392 (3)
C2—C41.512 (3)C12—C131.373 (4)
C2—H21.0000C12—H120.9500
C1A—C2A1.448 (4)C11A—C12A1.381 (4)
C1A—C3A1.524 (4)C11A—H11A0.9500
C1A—H1A1.0000C13—C141.389 (4)
C3—C51.548 (4)C13—H130.9500
C3—H31.0000C12A—C13A1.378 (4)
C2A—C4A1.514 (4)C12A—H12A0.9500
C2A—H2A1.0000C14—C151.371 (4)
C4—C61.534 (3)C14—H140.9500
C4—H41.0000C13A—C14A1.377 (4)
C3A—C5A1.543 (3)C13A—H13A0.9500
C3A—H3A1.0000C15—H150.9500
C5—C71.504 (4)C14A—C15A1.373 (4)
C5—C61.534 (3)C14A—H14A0.9500
C5—H51.0000C15A—H15A0.9500
C2—O1—C160.56 (19)C7A—C5A—C3A112.3 (2)
C4—O2—C397.91 (19)C6A—C5A—C3A101.7 (2)
C2A—O1A—C1A60.39 (17)C7A—C5A—H5A112.5
C4A—O2A—C3A97.55 (18)C6A—C5A—H5A112.5
C8—N1—C7113.4 (2)C3A—C5A—H5A112.5
C8—N1—C9122.1 (2)O3—C7—N1123.9 (3)
C7—N1—C9124.5 (2)O3—C7—C5127.9 (2)
C8A—N1A—C7A113.5 (2)N1—C7—C5108.2 (2)
C8A—N1A—C9A122.1 (2)C8A—C6A—C5A105.6 (2)
C7A—N1A—C9A124.5 (2)C8A—C6A—C4A112.0 (2)
O1—C1—C259.59 (17)C5A—C6A—C4A101.75 (19)
O1—C1—C3114.6 (2)C8A—C6A—H6A112.3
C2—C1—C3103.7 (2)C5A—C6A—H6A112.3
O1—C1—H1120.8C4A—C6A—H6A112.3
C2—C1—H1120.8O4—C8—N1123.8 (2)
C3—C1—H1120.8O4—C8—C6127.8 (2)
O1—C2—C159.84 (17)N1—C8—C6108.3 (2)
O1—C2—C4114.0 (2)O3A—C7A—N1A124.3 (2)
C1—C2—C4103.6 (2)O3A—C7A—C5A127.6 (2)
O1—C2—H2121.0N1A—C7A—C5A108.1 (2)
C1—C2—H2121.0N1—C9—C10112.5 (2)
C4—C2—H2121.0N1—C9—H9A109.1
O1A—C1A—C2A59.31 (17)C10—C9—H9A109.1
O1A—C1A—C3A113.4 (2)N1—C9—H9B109.1
C2A—C1A—C3A103.5 (2)C10—C9—H9B109.1
O1A—C1A—H1A121.3H9A—C9—H9B107.8
C2A—C1A—H1A121.3O4A—C8A—N1A123.9 (2)
C3A—C1A—H1A121.3O4A—C8A—C6A127.7 (2)
O2—C3—C1102.3 (2)N1A—C8A—C6A108.4 (2)
O2—C3—C5101.59 (19)C11—C10—C15118.9 (2)
C1—C3—C5104.7 (2)C11—C10—C9121.0 (2)
O2—C3—H3115.5C15—C10—C9120.1 (2)
C1—C3—H3115.5N1A—C9A—C10A112.3 (2)
C5—C3—H3115.5N1A—C9A—H9AA109.1
O1A—C2A—C1A60.30 (17)C10A—C9A—H9AA109.1
O1A—C2A—C4A113.5 (2)N1A—C9A—H9AB109.1
C1A—C2A—C4A103.3 (2)C10A—C9A—H9AB109.1
O1A—C2A—H2A121.1H9AA—C9A—H9AB107.9
C1A—C2A—H2A121.1C12—C11—C10120.0 (2)
C4A—C2A—H2A121.1C12—C11—H11120.0
O2—C4—C2102.6 (2)C10—C11—H11120.0
O2—C4—C6101.35 (18)C11A—C10A—C15A118.4 (2)
C2—C4—C6105.2 (2)C11A—C10A—C9A120.9 (2)
O2—C4—H4115.3C15A—C10A—C9A120.6 (2)
C2—C4—H4115.3C13—C12—C11121.1 (2)
C6—C4—H4115.3C13—C12—H12119.4
O2A—C3A—C1A102.6 (2)C11—C12—H12119.4
O2A—C3A—C5A101.52 (19)C12A—C11A—C10A120.4 (2)
C1A—C3A—C5A104.5 (2)C12A—C11A—H11A119.8
O2A—C3A—H3A115.5C10A—C11A—H11A119.8
C1A—C3A—H3A115.5C12—C13—C14119.2 (2)
C5A—C3A—H3A115.5C12—C13—H13120.4
C7—C5—C6105.3 (2)C14—C13—H13120.4
C7—C5—C3113.0 (2)C13A—C12A—C11A120.5 (3)
C6—C5—C3101.2 (2)C13A—C12A—H12A119.8
C7—C5—H5112.2C11A—C12A—H12A119.8
C6—C5—H5112.2C15—C14—C13120.4 (2)
C3—C5—H5112.2C15—C14—H14119.8
O2A—C4A—C2A103.0 (2)C13—C14—H14119.8
O2A—C4A—C6A102.10 (18)C14A—C13A—C12A119.5 (2)
C2A—C4A—C6A104.6 (2)C14A—C13A—H13A120.3
O2A—C4A—H4A115.1C12A—C13A—H13A120.3
C2A—C4A—H4A115.1C14—C15—C10120.4 (2)
C6A—C4A—H4A115.1C14—C15—H15119.8
C8—C6—C4110.64 (19)C10—C15—H15119.8
C8—C6—C5104.5 (2)C15A—C14A—C13A120.4 (2)
C4—C6—C5102.1 (2)C15A—C14A—H14A119.8
C8—C6—H6112.9C13A—C14A—H14A119.8
C4—C6—H6112.9C14A—C15A—C10A120.8 (2)
C5—C6—H6112.9C14A—C15A—H15A119.6
C7A—C5A—C6A104.5 (2)C10A—C15A—H15A119.6
C2—O1—C1—C3−92.0 (3)C3—C5—C7—N1108.6 (2)
C1—O1—C2—C492.3 (2)C7A—C5A—C6A—C8A−0.5 (3)
C3—C1—C2—O1110.7 (2)C3A—C5A—C6A—C8A−117.5 (2)
O1—C1—C2—C4−110.0 (2)C7A—C5A—C6A—C4A116.5 (2)
C3—C1—C2—C40.6 (3)C3A—C5A—C6A—C4A−0.5 (2)
C2A—O1A—C1A—C3A−92.2 (2)O2A—C4A—C6A—C8A78.5 (2)
C4—O2—C3—C151.7 (2)C2A—C4A—C6A—C8A−174.3 (2)
C4—O2—C3—C5−56.3 (2)O2A—C4A—C6A—C5A−33.8 (2)
O1—C1—C3—O230.2 (3)C2A—C4A—C6A—C5A73.3 (2)
C2—C1—C3—O2−32.3 (3)C7—N1—C8—O4−173.7 (2)
O1—C1—C3—C5135.8 (2)C9—N1—C8—O44.5 (4)
C2—C1—C3—C573.3 (2)C7—N1—C8—C65.3 (3)
C1A—O1A—C2A—C4A92.4 (2)C9—N1—C8—C6−176.4 (2)
C3A—C1A—C2A—O1A109.5 (2)C4—C6—C8—O464.3 (3)
O1A—C1A—C2A—C4A−109.7 (2)C5—C6—C8—O4173.5 (2)
C3A—C1A—C2A—C4A−0.2 (3)C4—C6—C8—N1−114.7 (2)
C3—O2—C4—C2−51.4 (2)C5—C6—C8—N1−5.5 (3)
C3—O2—C4—C657.2 (2)C8A—N1A—C7A—O3A178.5 (2)
O1—C2—C4—O2−31.2 (3)C9A—N1A—C7A—O3A−1.5 (4)
C1—C2—C4—O231.6 (2)C8A—N1A—C7A—C5A−0.8 (3)
O1—C2—C4—C6−136.8 (2)C9A—N1A—C7A—C5A179.3 (2)
C1—C2—C4—C6−74.1 (2)C6A—C5A—C7A—O3A−178.4 (2)
C4A—O2A—C3A—C1A51.5 (2)C3A—C5A—C7A—O3A−69.0 (3)
C4A—O2A—C3A—C5A−56.4 (2)C6A—C5A—C7A—N1A0.8 (3)
O1A—C1A—C3A—O2A30.2 (3)C3A—C5A—C7A—N1A110.2 (2)
C2A—C1A—C3A—O2A−31.8 (3)C8—N1—C9—C1066.0 (3)
O1A—C1A—C3A—C5A135.8 (2)C7—N1—C9—C10−116.0 (3)
C2A—C1A—C3A—C5A73.8 (3)C7A—N1A—C8A—O4A−178.0 (2)
O2—C3—C5—C7−79.3 (2)C9A—N1A—C8A—O4A1.9 (3)
C1—C3—C5—C7174.6 (2)C7A—N1A—C8A—C6A0.4 (3)
O2—C3—C5—C632.9 (2)C9A—N1A—C8A—C6A−179.6 (2)
C1—C3—C5—C6−73.3 (2)C5A—C6A—C8A—O4A178.5 (2)
C3A—O2A—C4A—C2A−51.9 (2)C4A—C6A—C8A—O4A68.5 (3)
C3A—O2A—C4A—C6A56.4 (2)C5A—C6A—C8A—N1A0.1 (2)
O1A—C2A—C4A—O2A−30.8 (3)C4A—C6A—C8A—N1A−109.8 (2)
C1A—C2A—C4A—O2A32.4 (3)N1—C9—C10—C11−135.3 (2)
O1A—C2A—C4A—C6A−137.2 (2)N1—C9—C10—C1544.8 (3)
C1A—C2A—C4A—C6A−74.0 (2)C8A—N1A—C9A—C10A69.9 (3)
O2—C4—C6—C875.3 (2)C7A—N1A—C9A—C10A−110.1 (3)
C2—C4—C6—C8−178.1 (2)C15—C10—C11—C12−1.8 (4)
O2—C4—C6—C5−35.4 (2)C9—C10—C11—C12178.2 (2)
C2—C4—C6—C571.2 (2)N1A—C9A—C10A—C11A41.6 (3)
C7—C5—C6—C83.8 (3)N1A—C9A—C10A—C15A−139.7 (2)
C3—C5—C6—C8−114.0 (2)C10—C11—C12—C130.5 (4)
C7—C5—C6—C4119.1 (2)C15A—C10A—C11A—C12A0.1 (4)
C3—C5—C6—C41.3 (2)C9A—C10A—C11A—C12A178.8 (3)
O2A—C3A—C5A—C7A−76.8 (2)C11—C12—C13—C140.9 (4)
C1A—C3A—C5A—C7A176.8 (2)C10A—C11A—C12A—C13A−0.3 (5)
O2A—C3A—C5A—C6A34.4 (2)C12—C13—C14—C15−1.2 (4)
C1A—C3A—C5A—C6A−72.0 (2)C11A—C12A—C13A—C14A−0.1 (4)
C8—N1—C7—O3175.9 (2)C13—C14—C15—C10−0.1 (4)
C9—N1—C7—O3−2.3 (4)C11—C10—C15—C141.6 (4)
C8—N1—C7—C5−2.7 (3)C9—C10—C15—C14−178.5 (2)
C9—N1—C7—C5179.0 (2)C12A—C13A—C14A—C15A0.8 (4)
C6—C5—C7—O3−179.6 (2)C13A—C14A—C15A—C10A−1.0 (4)
C3—C5—C7—O3−70.0 (3)C11A—C10A—C15A—C14A0.5 (4)
C6—C5—C7—N1−0.9 (3)C9A—C10A—C15A—C14A−178.2 (2)
Listed surface atom contacts and their percentage contribution to total contacts top
Atom contactContribution (%)
H···O/O···H43.3
H···H39.6
H···C/C···H14.8
H···N/N···H1.1
O···O0.7
C···O/O···C0.6
 

Acknowledgements

BNB, MHM, and DCF would like to thank the Department of Chemistry, Honors College, Office of Undergraduate Research, and University of South Alabama Foundation for their generous financial support of undergraduate research. JFD would like to thank Megan Ariki and Aaron Erlich for helping conduct the CSD database survey. JFD would like to thank Matthias Zeller for helpful feedback regarding crystal analysis.

Funding information

Funding for this research was provided by: The Department of Department of Chemistry: Honors College, University of South Alabama's Office of Undergraduate Research; JSPS and Nagoya University through The World Premier International Research Initiative (WPI) program.

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ISSN: 2056-9890
Volume 82| Part 10| October 2026|
https://doi.org/10.1107/S2056989026009205