Crystal structure and Hirshfeld surface analysis of aqua­(1H-imidazole-κN3)[N-(2-oxido­benzyl­idene)threonato-κ3O,N,O′]zinc(II)

Yoshizawa, F.; Okui, A.; Nakane, D.; Akitsu, T.

doi:10.1107/S2056989025002385

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ISSN: 2056-9890

Volume 81| Part 4| April 2025| Pages 332-335

https://doi.org/10.1107/S2056989025002385

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Crystal structure and Hirshfeld surface analysis of aqua(1H-imidazole-κN³)[N-(2-oxidobenzylidene)threonato-κ³O,N,O′]zinc(II)

Fumishi Yoshizawa,^a Anna Okui,^a Daisuke Nakane ^a and Takashiro Akitsu ^a ^*

^aDepartment of Chemistry, Faculty of Science, Tokyo University of Science, 1-3, Kagurazaka, Shinjuku-ku, Tokyo 162-8601, Japan
^*Correspondence e-mail: akitsu2@rs.tus.ac.jp

Edited by Y. Ozawa, University of Hyogo, Japan (Received 18 February 2025; accepted 16 March 2025; online 25 March 2025)

The title complex, [Zn(C₁₁H₁₁NO₄)(C₃H₄N₂)(H₂O)], which includes a tridentate ligand, was synthesized from L-threonine and salicylaldehyde. One water molecule and one imidazole molecule additionally coordinate the zinc(II) center in a distorted trigonal–bipyramidal geometry. The crystal structure features N—H⋯O and O—H⋯O hydrogen bonds. A Hirshfeld surface analysis indicates that the most important contributions to the packing are from H⋯H/H⋯H (50.7%) and O⋯H/H⋯O (25.0%) contacts.

Keywords: Schiff base ligand; zinc(II) complex; amino acid; Hirshfeld surface analysis; crystal structure.

CCDC reference: 2431599

1. Chemical context

Amino acid Schiff bases have an azomethine (C=N) group synthesized by mixing primary amines and formyls, and are used as organic ligands (Katsuumi et al., 2020 ; Hirotsu et al., 2022 ; Gozdas et al., 2024 ; Bowman et al., 2021 ). According to a review on the synthesis of amino acid Schiff base–metal complexes (Akitsu et al., 2022 ), in general, Schiff bases and their metal complexes are versatile compounds and are widely used in many research and industrial applications. For example, supramolecular encapsulation of nanocrystalline Schiff bases in β-cyclodextrin (Mahato et al., 2022 ), photoreaction with titanium dioxide (Takeshita & Akitsu, 2015 ), photocatalytic reduction of hexavalent chromium (Nakagame et al., 2019 ; Miyagawa et al., 2020 ), Schiff base ligand–SPCE (screen-printed carbon electrode) sensors (Bressi et al., 2022 ), and flexible ruthenium(II) Schiff base complexes, which have been shown to play a key role in drug activity upon photoirradiation (Gillard et al., 2020 ).

Furthermore, Schiff base complexes are considered an important class of organic compounds with a wide range of biological properties, including free-radical-scavenging activity, antibacterial activity, and antitumor activity (Kumar, 2022 ). In our laboratory, we synthesized novel mono-chlorinated Schiff base copper(II) complexes and tested their antibacterial activity against Gram-positive and Gram-negative bacteria. The most active compounds were then tested for antioxidant activity, and it was found that E. coli absorbed these compounds with very high affinity (Otani et al., 2022 ). We are also conducting research using microfluidic devices to efficiently synthesize amino acid Schiff base copper(II) complexes (Kobayashi et al., 2023 ), and synthesis of amino acid Schiff base copper(II) complexes containing azobenzene moiety (Kaneda et al., 2024 ). Our goal is to evaluate the SOD activity of artificial metalloproteins made by conjugating these Schiff base copper(II) complexes with proteins such as lysozyme (Furuya et al., 2023 ; Nakane et al., 2024 ).

Therefore, we have been studying the bioactivity of Schiff base complexes derived from amino acids and decided to synthesize a zinc complex of this ligand to compare its bioactivity with that of the copper complex. In this report, we describe the crystal structure and intermolecular interactions of the zinc(II) complex, coordinated with imidazole as a model for histidine residues in proteins.

2. Structural commentary

The molecular structure of the title compound consists of one imidazole molecule, one water molecule and a tridentate ligand, which is synthesized from L-threonine and salicylaldehyde, coordinating to a zinc(II) center in distorted trigonal–bipyramidal geometry (Fig. 1). The two largest coordination angles O1—Zn01—O2 and N1—Zn01—O5 are 166.60 (11), 130.65 (13)°, and the τ value derived from them, which is five-coordinated geometry index, is 0.599 (Addison et al., 1984 ). The C7—N1 distance is 1.276 (5) Å, which is close to a typical C=N double-bond length for an imine (Katsuumi et al., 2020). The Zn01—O1, Zn01—O2 and Zn01—O5 coordination lengths are 2.061 (2), 2.117 (3) and 1.996 (3) Å, respectively, close to a typical Zn—O bond length (Noor et al., 2021 ). The Zn01—N1 and Zn1—N2 bonds of 2.038 (3) and 2.015 (3) Å corresponds to a typical Zn—N bond length (Noor et al., 2021). These five atoms coordinating to Zn1 have similar bond distances.

Figure 1
The molecular structure of the title compound with ellipsoids drawn at the 50% probability level.

3. Supramolecular features

Four intermolecular hydrogen bonds are observed in the crystal (Fig. 2); two hydrogen bonds (O5—H16A⋯O1 and O5H—H16B⋯O3) lead to the formation of a chain structure along the a-axis direction. One hydrogen bond (O4—H15⋯O2) is formed along the c-axis direction (Table 1). In addition, an intermolecular N3—H17⋯O1 interaction is found (symmetry codes given in Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H15⋯O2ⁱ	0.79 (7)	1.89 (7)	2.678 (4)	170 (8)
O5—H16A⋯O1ⁱⁱ	0.79 (7)	1.91 (7)	2.708 (4)	178 (6)
O5—H16B⋯O3ⁱ	0.72 (8)	2.02 (8)	2.724 (4)	165 (7)
N3—H17⋯O1ⁱⁱⁱ	0.88	2.06	2.830 (6)	145
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z]$ ; (ii) ; (iii) .

Figure 2
A view of the O—H⋯O and N—H⋯O hydrogen bonds, shown as dashed lines. [Symmetry codes: (i) −x + $[{3\over 2}]$ , y − $[{1\over 2}]$ , −z; (ii) −x + 1, y, −z; (iii) x, y + 1, z.]

A Hirshfeld surface analysis (McKinnon et al., 2007 ; Spackman & Jayatilaka, 2009 ) was performed to further investigate the intermolecular interactions and contacts. The intermolecular O—H⋯O hydrogen bonds are indicated by bright red spots appearing near O on the Hirshfeld surfaces mapped over d_norm and by two sharp spikes of almost the same length in the region 1.6 Å < (d_e + d_i) < 2.0 Å in the 2D fingerprint plots (Fig. 3).

Figure 3
Hirshfeld surfaces mapped over d_norm and the two-dimensional fingerprint plots.

The contributions to the packing from H⋯H, C⋯C, C⋯H/H⋯C, N⋯H/H⋯N, and H⋯O/O⋯H contacts are 50.7, 3.3, 14.9, 4.3 and 25.0%, respectively. The structure is characterized by high proportion of H⋯H interactions, where H⋯H are van der Waals interactions. The high value of C⋯H/H⋯C is thought to arise from C—H⋯π interactions due to the presence of aromatic rings in the compound. The low value of C⋯C is the result of the low contribution of π–π stacking due to non-overlapping aromatic rings in the structure.

4. Database survey

A search in the Cambridge Structural Database (CSD, Version 5.43, update of November 2021; Groom et al., 2016 ) for similar structures returned four relevant entries: aqua-[N-{[2-oxyphenyl]methylidene}threoninato]-(methanol)copper(II) (YUYFUW; Katsuumi et al., 2020), oxonium bis{2-[(tetrahydrofuran-2-ylmethyl)carbonoimidoyl]phenolato}zinc(II) perchlorate (KOVRAQ; Mandal et al., 2014 ), (3-(4-hydroxyphenyl)-2-{[(2-oxidophenyl)methylidene]amino}propanoato)(1H-imidazole)copper(II) (GIQWUC; Suzuki et al., 2023 ), mono/bis(aqua-κO)[N-(2-oxidobenzylidene)valinato-κ³O,N,O′]copper(II) (VEXZIL; Akiyama et al., 2023 ).

5. Synthesis and crystallization

L-threonine (11.912 mg, 0.10 mmol) was reacted with salicylaldehyde (12.212 mg, 0.10 mmol) in methanol (5 mL) and water (2 mL), and the resulting mixture was stirred at 313 K for 1 h to afford a yellow solution. To this solution, zinc(II) acetate dihydrate (21.951 mg, 0.100 mmol) was added and it was stirred at 313 K for 1 h. Then imidazole (6.808 mg, 0.10 mmol) was added, yielding a pale-yellow solution. For crystallization, the solution was placed in air at 300 K for several days, and the title complex was obtained as pale yellow columnar-shaped single crystals suitable for single-crystal X-ray diffraction structure analysis. All reagents are commercially available, but L-threonine moiety may partially racemize during synthesis. IR (ATR): 1070 cm⁻¹(w), 1284 cm⁻¹(m), 1376 cm⁻¹(m), 1473 cm⁻¹(m), 1475 cm⁻¹(m), 1548 cm⁻¹(w, C=C double bond), 1622 cm⁻¹(s, C=O double bond), 1634 cm⁻¹(s, C=N double bond), 3251 cm⁻¹(br, O—H). UV-vis (H₂O): 270 nm (ɛ = 38000 L mol⁻¹ cm⁻¹, π–π*); 359 nm (ɛ = 18000 L mol⁻¹ cm⁻¹, n–π*).

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. All C-bound H atoms were placed in geometrically calculated positions (C—H = 0.94–1.00 Å) and were constrained using a riding model with U_iso(H) = 1.2U_eq(C) for R₂CH and R₃CH H atoms and 1.5U_eq(C) for the methyl H atoms. The N-bound H atom H17 was constrained using a riding model with U_iso(H) = 1.2U_eq(N), and the O-bound H atoms H15, H16A, H16B were located based on a difference-Fourier map and refined freely.

Table 2
Experimental details

Crystal data
Chemical formula	[Zn(C₁₁H₁₁NO₄)(C₃H₄N₂)(H₂O)]
M_r	372.67
Crystal system, space group	Monoclinic, C2
Temperature (K)	173
a, b, c (Å)	18.3835 (7), 7.7141 (3), 13.3800 (5)
β (°)	123.787 (1)
V (Å³)	1576.99 (11)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	1.59
Crystal size (mm)	0.10 × 0.10 × 0.10

Data collection
Diffractometer	Bruker-AXS D8 QUEST
Absorption correction	Multi-scan
T_min, T_max	0.64, 0.86
No. of measured, independent and observed [I > 2σ(I)] reflections	10846, 2752, 2701
R_int	0.073
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.074, 1.07
No. of reflections	2752
No. of parameters	218
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.29
Absolute structure	Flack x determined using 1180 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	0.143 (11)
Computer programs: APEX2 and SAINT (Bruker, 2019 ), SHELXT2018/2 (Sheldrick, 2015a ), SHELXL2019/1 (Sheldrick, 2015b ) and ShelXle (Hübschle et al., 2011 ).

Supporting information

CCDC reference: 2431599

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989025002385/ox2014sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989025002385/ox2014Isup2.hkl

checkCIF report

Computing details top

Aqua(1H-imidazole-κN³)[N-(2-oxidobenzylidene)threonato-κ³O,N,O']zinc(II) top

Crystal data top

[Zn(C₁₁H₁₁NO₄)(C₃H₄N₂)(H₂O)]	F(000) = 768
M_r = 372.67	D_x = 1.570 Mg m⁻³
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
a = 18.3835 (7) Å	Cell parameters from 6515 reflections
b = 7.7141 (3) Å	θ = 3.0–25.0°
c = 13.3800 (5) Å	µ = 1.59 mm⁻¹
β = 123.787 (1)°	T = 173 K
V = 1576.99 (11) Å³	Prism, yellow
Z = 4	0.10 × 0.10 × 0.10 mm

Data collection top

Bruker-AXS D8 QUEST diffractometer	2701 reflections with I > 2σ(I)
Detector resolution: 7.3910 pixels mm^-1	R_int = 0.073
profile data from θ/2θ scans	θ_max = 25.1°, θ_min = 3.0°
Absorption correction: multi-scan	h = −21→21
T_min = 0.64, T_max = 0.86	k = −9→9
10846 measured reflections	l = −15→15
2752 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.032	w = 1/[σ²(F_o²) + (0.0364P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.074	(Δ/σ)_max < 0.001
S = 1.07	Δρ_max = 0.35 e Å⁻³
2752 reflections	Δρ_min = −0.29 e Å⁻³
218 parameters	Absolute structure: Flack x determined using 1180 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: 0.143 (11)

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

	x	y	z	U_iso*/U_eq
Zn01	0.65438 (2)	0.42759 (7)	0.11898 (3)	0.01670 (17)
O1	0.59603 (16)	0.2984 (3)	0.1916 (2)	0.0174 (5)
O2	0.74153 (18)	0.5370 (4)	0.0799 (3)	0.0323 (7)
O3	0.8834 (2)	0.5634 (5)	0.1533 (3)	0.0391 (8)
O4	0.7676 (2)	0.1327 (5)	0.1191 (3)	0.0372 (8)
O5	0.5804 (2)	0.3045 (4)	−0.0380 (3)	0.0276 (7)
H16A	0.529 (5)	0.302 (8)	−0.085 (6)	0.041000*
N1	0.7722 (2)	0.3625 (4)	0.2698 (3)	0.0196 (7)
N2	0.6124 (2)	0.6638 (4)	0.1298 (3)	0.0241 (7)
N3	0.6028 (3)	0.9438 (6)	0.1430 (3)	0.0420 (10)
H17	0.611949	1.055498	0.141612	0.050000*
H15	0.768 (5)	0.115 (10)	0.061 (6)	0.063000*
C1	0.6293 (2)	0.2935 (5)	0.3089 (3)	0.0187 (7)
C2	0.5734 (3)	0.2624 (6)	0.3481 (4)	0.0273 (9)
H2	0.512602	0.246220	0.290352	0.033000*
C3	0.6056 (3)	0.2549 (7)	0.4692 (4)	0.0365 (11)
H3	0.566229	0.235803	0.492934	0.044000*
C4	0.6946 (3)	0.2747 (7)	0.5573 (4)	0.0372 (11)
H4	0.716190	0.269067	0.640331	0.045000*
C5	0.7501 (3)	0.3026 (7)	0.5208 (4)	0.0339 (10)
H5	0.810969	0.314747	0.580187	0.041000*
C6	0.7204 (3)	0.3139 (5)	0.3988 (3)	0.0221 (8)
C7	0.7866 (3)	0.3359 (6)	0.3735 (3)	0.0230 (8)
H7	0.845966	0.330118	0.439697	0.028000*
C8	0.8438 (2)	0.3703 (5)	0.2529 (3)	0.0225 (8)
H8	0.899618	0.402041	0.330026	0.027000*
C9	0.8220 (3)	0.5031 (6)	0.1559 (4)	0.0268 (9)
C10	0.8523 (3)	0.1890 (6)	0.2094 (4)	0.0297 (9)
H10	0.887625	0.201059	0.173851	0.036000*
C11	0.8964 (4)	0.0585 (8)	0.3105 (6)	0.0507 (14)
H11A	0.955393	0.099246	0.372280	0.076000*
H11B	0.900354	−0.053288	0.279021	0.076000*
H11C	0.862170	0.045004	0.345727	0.076000*
C12	0.5546 (3)	0.6991 (6)	0.1608 (4)	0.0295 (9)
H12	0.523720	0.613729	0.174295	0.035000*
C13	0.5472 (3)	0.8718 (6)	0.1695 (4)	0.0381 (11)
H13	0.511549	0.930343	0.189603	0.046000*
C14	0.6408 (3)	0.8169 (7)	0.1196 (4)	0.0346 (10)
H14	0.681965	0.833681	0.098842	0.041000*
H16B	0.599 (5)	0.243 (10)	−0.059 (6)	0.052000*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn01	0.0144 (2)	0.0149 (2)	0.0197 (2)	−0.00040 (18)	0.00884 (17)	0.00248 (17)
O1	0.0165 (12)	0.0172 (13)	0.0178 (11)	−0.0024 (11)	0.0091 (10)	−0.0005 (10)
O2	0.0171 (14)	0.0431 (19)	0.0350 (15)	0.0022 (13)	0.0133 (12)	0.0193 (14)
O3	0.0215 (15)	0.045 (2)	0.0486 (18)	−0.0046 (14)	0.0184 (13)	0.0176 (16)
O4	0.0358 (17)	0.045 (2)	0.0399 (17)	−0.0091 (15)	0.0269 (15)	−0.0134 (16)
O5	0.0164 (14)	0.0383 (19)	0.0231 (14)	0.0040 (14)	0.0080 (12)	−0.0115 (13)
N1	0.0190 (15)	0.0173 (14)	0.0238 (15)	0.0012 (13)	0.0127 (13)	0.0015 (12)
N2	0.0222 (16)	0.0146 (17)	0.0257 (16)	−0.0017 (13)	0.0073 (13)	0.0010 (13)
N3	0.048 (2)	0.0124 (18)	0.0373 (18)	0.0022 (19)	0.0066 (16)	−0.0011 (18)
C1	0.0222 (18)	0.0121 (17)	0.0214 (17)	0.0030 (15)	0.0119 (15)	−0.0014 (14)
C2	0.025 (2)	0.034 (2)	0.029 (2)	0.0011 (18)	0.0186 (17)	−0.0006 (18)
C3	0.037 (2)	0.050 (3)	0.034 (2)	0.002 (2)	0.027 (2)	0.001 (2)
C4	0.038 (2)	0.057 (3)	0.0196 (19)	0.007 (2)	0.0182 (18)	0.002 (2)
C5	0.030 (2)	0.045 (3)	0.0198 (19)	0.004 (2)	0.0099 (17)	0.0006 (19)
C6	0.0226 (18)	0.024 (2)	0.0195 (17)	0.0026 (16)	0.0113 (15)	−0.0012 (15)
C7	0.0178 (17)	0.024 (2)	0.0192 (18)	0.0008 (15)	0.0053 (15)	0.0020 (15)
C8	0.0116 (16)	0.027 (2)	0.0259 (18)	−0.0022 (15)	0.0085 (15)	0.0012 (15)
C9	0.022 (2)	0.026 (2)	0.034 (2)	−0.0045 (18)	0.0170 (18)	0.0028 (18)
C10	0.025 (2)	0.033 (2)	0.039 (2)	0.0010 (18)	0.0230 (19)	0.0036 (19)
C11	0.062 (3)	0.036 (3)	0.066 (3)	0.023 (3)	0.042 (3)	0.018 (3)
C12	0.024 (2)	0.021 (2)	0.033 (2)	0.0022 (17)	0.0095 (18)	−0.0052 (17)
C13	0.035 (2)	0.026 (2)	0.039 (2)	0.0076 (18)	0.0116 (19)	−0.0052 (18)
C14	0.036 (2)	0.023 (3)	0.030 (2)	−0.003 (2)	0.0088 (19)	0.0024 (17)

Geometric parameters (Å, º) top

Zn01—O5	1.996 (3)	N3—C14	1.337 (7)
Zn01—N2	2.015 (3)	N3—C13	1.371 (7)
Zn01—N1	2.038 (3)	C1—C2	1.410 (6)
Zn01—O1	2.060 (2)	C1—C6	1.427 (5)
Zn01—O2	2.117 (3)	C2—C3	1.383 (6)
O1—C1	1.331 (4)	C3—C4	1.394 (7)
O2—C9	1.272 (5)	C4—C5	1.371 (7)
O3—C9	1.238 (5)	C5—C6	1.407 (6)
O4—C10	1.408 (6)	C6—C7	1.443 (6)
N1—C7	1.276 (5)	C8—C9	1.522 (6)
N1—C8	1.456 (5)	C8—C10	1.556 (6)
N2—C14	1.327 (6)	C10—C11	1.509 (7)
N2—C12	1.366 (6)	C12—C13	1.351 (7)

O5—Zn01—N2	116.22 (13)	C2—C1—C6	117.4 (3)
O5—Zn01—N1	130.65 (13)	C3—C2—C1	121.2 (4)
N2—Zn01—N1	112.96 (13)	C2—C3—C4	121.5 (4)
O5—Zn01—O1	92.14 (12)	C5—C4—C3	118.1 (4)
N2—Zn01—O1	94.77 (12)	C4—C5—C6	122.5 (4)
N1—Zn01—O1	87.64 (11)	C5—C6—C1	119.2 (4)
O5—Zn01—O2	95.52 (13)	C5—C6—C7	116.4 (4)
N2—Zn01—O2	91.69 (14)	C1—C6—C7	124.2 (3)
N1—Zn01—O2	79.03 (12)	N1—C7—C6	125.5 (4)
O1—Zn01—O2	166.60 (11)	N1—C8—C9	109.2 (3)
C1—O1—Zn01	123.4 (2)	N1—C8—C10	108.0 (3)
C9—O2—Zn01	115.1 (3)	C9—C8—C10	108.7 (3)
C7—N1—C8	121.1 (3)	O3—C9—O2	124.9 (4)
C7—N1—Zn01	125.5 (3)	O3—C9—C8	117.8 (4)
C8—N1—Zn01	113.0 (2)	O2—C9—C8	117.2 (3)
C14—N2—C12	105.7 (4)	O4—C10—C11	110.5 (4)
C14—N2—Zn01	127.5 (3)	O4—C10—C8	107.7 (3)
C12—N2—Zn01	126.5 (3)	C11—C10—C8	112.3 (4)
C14—N3—C13	108.9 (5)	C13—C12—N2	110.8 (5)
O1—C1—C2	119.4 (3)	C12—C13—N3	104.6 (5)
O1—C1—C6	123.1 (3)	N2—C14—N3	110.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H15···O2ⁱ	0.79 (7)	1.89 (7)	2.678 (4)	170 (8)
O5—H16A···O1ⁱⁱ	0.79 (7)	1.91 (7)	2.708 (4)	178 (6)
O5—H16B···O3ⁱ	0.72 (8)	2.02 (8)	2.724 (4)	165 (7)
N3—H17···O1ⁱⁱⁱ	0.88	2.06	2.830 (6)	145
C14—H14···O2	0.95	2.61	3.077 (6)	111
C13—H13···O3^iv	0.95	2.36	3.253 (6)	156
C2—H2···O3^v	0.95	2.48	3.351 (5)	152

Symmetry codes: (i) −x+3/2, y−1/2, −z; (ii) −x+1, y, −z; (iii) x, y+1, z; (iv) x−1/2, y+1/2, z; (v) x−1/2, y−1/2, z.

Funding information

Funding for this research was provided by: Grant-in-Aid for Scientific Research (B) KAKENHI (24K00912).

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