Crystal structure of a 2:1 co-crystal of the anti­cancer drug lenalidomide with 1,3-resorcinol

Kaldoke, S.; Dabke, N.B.; Shet, N.; Gonnade, R.G.

doi:10.1107/S205698902601114X

research communications

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ISSN: 2056-9890

Volume 82| Part 11| November 2026| Pages 1371-1375

https://doi.org/10.1107/S205698902601114X

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Crystal structure of a 2:1 co-crystal of the anticancer drug lenalidomide with 1,3-resorcinol

Sejal Kaldoke,^a Niteen B. Dabke,^a,^b Nagabhushan Shet ^a,^b and Rajesh G. Gonnade ^a,^b ^*

^aPhysical and Materials Chemistry Division, CSIR-National Chemical Laboratory, Dr. Homi Bhabha Road, Pashan, Pune, Maharashtra, 411008, India, and ^bAcademy of Scientific and Innovative Research (AcSIR), Ghaziabad 201002, India
^*Correspondence e-mail: [email protected]

Edited by D. Chopra, Indian Institute of Science Education and Research Bhopal, India (Received 9 October 2026; accepted 27 October 2026; online 30 October 2026)

A 2:1 cocrystal of lenalidomide and 1,3-resorcinol [systematic name: 3-(4-amino-1-oxo-1,3-dihydro-2H-isoindol-2-yl)piperidine-2,6-dione–benzene-1,3-diol (2/1), 2C₁₃H₁₃N₃O₃·C₆H₆O₂] was synthesized, and its crystal structure was elucidated by single-crystal X-ray diffraction (SCXRD). The cocrystal crystallizes in the triclinic space group P1. The two symmetry-independent lenalidomide molecules form a hydrogen-bonded dimeric assembly through N—H⋯O interactions, generating an R₂²(8) ring motif. In addition, O—H⋯O hydrogen bonds involving the hydroxyl groups of 1,3-resorcinol and the carbonyl oxygen atoms of the isoindolinone and glutarimide moieties of lenalidomide further contribute to the cohesion and organization of the crystal packing. The crystal structure is further consolidated by several close π–π stacking interactions involving the π-electrons of the isoindolinone moiety. Hirshfeld surface analysis and the corresponding two-dimensional fingerprint plots were employed to identify and quantify the principal intermolecular contacts contributing to the cohesion of the cocrystal structure.

Keywords: crystal structure; anticancer; lenalidomide; hydrogen bond; π-stacking.

CCDC reference: 2598460

1. Chemical context

Lenalidomide (LEN), a synthetic thalidomide analogue, is an immunomodulatory drug used in the treatment of multiple myeloma and myelodysplastic syndromes associated with deletion of chromosome 5q [del(5q)] (Richardson et al., 2002 ; List et al., 2006 ). Reported pharmacological effects include immunomodulatory and antiangiogenic activity (Kotla et al., 2009 ). Also in multiple myeloma, lenalidomide has also been shown to promote cereblon-dependent degradation of IKZF1 and IKZF3 (Krönke et al., 2014 ). The solid-state landscape of LEN includes anhydrous and hydrated forms, polymorphs and solvates (Ravikumar & Sridhar, 2009 ; Chennuru et al., 2017 ; Jia et al., 2019 ). Cocrystals of LEN with urea and 3,5-dihydroxybenzoic acid, gallic acid and nicotinamide have been reported, with selected systems showing changes in apparent solubility or dissolution under the conditions studied (Song et al., 2014 , Song et al., 2015 ; Wang et al., 2022 ). A crystalline form of lenalidomide (LEN) with resorcinol (RES) was previously disclosed in patent US 12098136 B2, accompanied by DSC, PXRD and NMR data; however, its crystal structure was not reported (Bhat et al., 2024 ). Here, we report the single-crystal X-ray structure of the LEN:RES cocrystal (2:1), providing a crystallographic description of its molecular arrangement and intermolecular interactions.

2. Structural commentary

The crystal structure of the LEN:RES (2:1) cocrystal was unambiguously established by single-crystal X-ray diffraction (SCXRD) analysis. The cocrystal crystallizes in the triclinic crystal system with the centrosymmetric space group P $[\overline{1}]$ (space group No. 2). The asymmetric unit comprises two independent molecules of LEN and one molecule of RES, corresponding to a 2:1 stoichiometric ratio (Fig. 1a). The two crystallographically independent LEN molecules are designated A and B. A structural overlay of molecules A and B reveals a distinct conformational difference in the glutarimide ring (Fig. 1b). The dihedral angle between a plane between the isoindolinone-derived aromatic system and the glutarimide ring is 86.93 (3)° for molecule A and 78.96 (3)° for molecule B. Thus, molecule A adopts a more orthogonal, and consequently less twisted, conformation with respect to the defined ring planes than molecule B. The molecules present in the asymmetric unit are interconnected through a network of hydrogen-bonding interactions. The two crystallographically independent LEN molecules, A and B, are connected through N—H⋯O hydrogen bonds, generating a cyclic R₂²(8) ring motif. In addition, the RES molecule participates in O—H⋯O hydrogen bonding engaging its hydroxyl group with the carbonyl oxygen atom of adjacent LEN molecule B, thereby further linking the molecular components within the asymmetric unit.

Figure 1
(a) The LEN:RES cocrystal with thermal displacement ellipsoids drawn at the 30% probability level. Atom labelling is provided for identification; hydrogen atoms are depicted as spheres of arbitrary radii for clarity. Hydrogen-bonding interactions are shown as violet dashed lines. (b) Overlay of two symmetry-independent molecules of LEN within the asymmetric unit of the LEN:RES cocrystal.

3. Supramolecular features

The molecular packing viewed along the b axis reveals that the LEN molecules are arranged along the a-axis direction through short π–π stacking interactions involving the isoindolinone moiety, with centroid-to-centroid distances ranging from 3.5410 (15) to 4.0014 (17) Å (see entries 14-25 of Table 1). These interactions generate a stacked one-dimensional supramolecular assembly extending along the a-axis direction. The stacked assemblies are further connected along the c-axis direction through dimeric C—H⋯O and N—H⋯O hydrogen-bonding interactions (C31—H31B⋯O2^vii, N3—H3⋯O8, and N6—H6⋯O2; Table 1), both forming cyclic R₂²(8) ring motifs. Consequently, an extended and compact supramolecular architecture is generated in the ac plane (Fig. 2). The packing arrangement viewed along the a-axis shows that the RES molecule is positioned between two LEN molecules and is involved in N—H⋯O (N2—H2B⋯O5ⁱⁱ and N3—H3⋯O1^iv), O—H⋯O (O5—H5A⋯O6) and C—H⋯π (C10—H10A⋯Cg9ⁱⁱ) interactions. In particular, C—H⋯π interactions occur between the hydrogen atoms associated with the glutarimide moiety of LEN and the π-electron cloud of the aromatic ring of RES, contributing to the formation of a one-dimensional supramolecular assembly along the b-axis direction. In addition, in the packing along the c-axis direction, RES interacts with adjacent LEN molecules through C—H⋯O contacts involving hydrogen atoms of RES and the carbonyl oxygen atoms of the glutarimide moieties of LEN (Fig. 3). These intermolecular interactions collectively consolidate the three-dimensional crystal packing.

Table 1
Hydrogen-bond geometry (Å, °)

Ring centroids are defined as: Cg1 = N1/C7/C1/C2/C8; Cg2 = N3/C9–C13; Cg3 = C1–C6;Cg5 = N4/C20/C25–C27; Cg6 = N6/C28–C32; Cg7 = C20–C25; and Cg9 = C14–C19. Cg⋯Cg denotes the centroid—centroid distance associated with π–π interactions.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H1⋯O8ⁱ	0.93 (3)	1.92 (3)	2.816 (3)	161 (3)
O5—H5A⋯O6	0.85 (3)	1.87 (3)	2.710 (3)	171 (3)
N2—H2B⋯O5ⁱⁱ	0.78 (3)	2.56 (3)	3.310 (3)	163 (3)
N2—H2A⋯O5ⁱⁱⁱ	0.83 (3)	2.28 (3)	3.015 (3)	148 (3)
N3—H3⋯O1^iv	0.89 (2)	2.31 (2)	3.022 (3)	137 (2)
N3—H3⋯O8	0.89 (2)	2.51 (2)	3.256 (3)	141 (2)
N5—H1D⋯O2^v	0.92 (3)	2.23 (3)	3.144 (3)	172 (2)
N6—H6⋯O2	0.92 (3)	2.00 (3)	2.915 (3)	171 (2)
C9—H9⋯O3^iv	0.98	2.65	3.409 (3)	135
C17—H17⋯O4^vi	0.93	2.57	3.263 (3)	131
C27—H27B⋯O7	0.97	2.58	3.106 (3)	114
C31—H31B⋯O2^vii	0.97	2.47	3.440 (3)	178
C10—H10A⋯Cg9ⁱⁱ		2.65	3.581 (3)	161
Cg1⋯Cg7ⁱⁱⁱ			3.7109 (16)
Cg1⋯Cg7^viii			4.0014 (17)
Cg3⋯Cg5ⁱⁱⁱ			3.7997 (17)
Cg3⋯Cg5^viii			3.9603 (17)
Cg3⋯Cg7ⁱⁱⁱ			3.6971 (17)
Cg3⋯Cg7^viii			3.6644 (17)
Cg3⋯Cg8ⁱⁱⁱ			3.5854 (15)
Cg3⋯Cg8^viii			3.6382 (15)
Cg4⋯Cg7ⁱⁱⁱ			3.5410 (15)
Cg4⋯Cg7^viii			3.6602 (15)
Cg4⋯Cg8ⁱⁱⁱ			3.6763 (13)
Cg4⋯Cg8^viii			3.8723 (13)
Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) .

Figure 2
View of the molecular packing along the b axis in the LEN:RES cocrystal, showing the intermolecular C—H⋯O and N—H⋯O hydrogen bonds and π–π stacking interactions.

Figure 3
View of the molecular packing along the a axis in the LEN:RES cocrystal, joined using C—H⋯O, N—H⋯O, O—H⋯O and C—H⋯π interactions.

4. Hirshfeld surface analysis

Hirshfeld surface (HS) analysis (Spackman & Jayatilaka, 2009 ) and two-dimensional fingerprint plots (Spackman & McKinnon, 2002 ) were performed using CrystalExplorer (Spackman et al., 2021 ). The Hirshfeld surface mapped over d_norm for molecule B of LEN in the cocrystal reveals several prominent red spots, indicating close contacts between LEN and RES. The Hirshfeld surface analysis was performed only for molecule B of LEN because it participates in O—H⋯O hydrogen bonding with the RES coformer, and N—H⋯O hydrogen bonding with molecule A of LEN, forming a dimeric motif. One of the most prominent red spots corresponds to the strong O—H⋯O hydrogen-bonding interaction between the hydroxyl group of RES and the carbonyl oxygen atom of LEN. The other prominent red spots are associated with N—H⋯O hydrogen-bonding interactions, which generate an R₂²(8) hydrogen-bonded ring motif (Fig. 4). The two-dimensional fingerprint plots further illustrate the principal intermolecular contacts contributing to the consolidation of the cocrystal structure. In particular, the H⋯H and O⋯H/H⋯O contacts exhibit prominent features at (d_i + d_e) values of approximately 2.4 and 2.0 Å, respectively (Fig. 5). These values are shorter than the corresponding sums of the van der Waals radii, indicating the presence of significant close intermolecular contacts.

Figure 4
Visualization of the Hirshfeld surface of molecule B of LEN, within the LEN:RES cocrystal.

Figure 5
Two-dimensional fingerprint plot of molecule B of LEN in the LEN:RES cocrystal, showing the percentage contributions of different intermolecular interactions to the Hirshfeld surface area.

5. Database survey

A survey of the Cambridge Structural Database (CSD, Version 6.01, Groom et al., 2016 ) using ConQuest (Bruno et al., 2002 ) identified 16 crystal structures based on LEN. Among these, two structures correspond to polymorphs of LEN (AJISES; Ravikumar & Sridhar, 2009, AJISES01; Chennuru et al., 2017), while two are hydrate forms (AJISIW; Ravikumar & Sridhar, 2009, ICOSUR; Chennuru et al., 2017). Solvate structures containing DMF (ICOTEC; Chennuru et al., 2017), acetone (ICOTIG; Chennuru et al., 2017), DMSO (ICOTOM; Chennuru et al., 2017), and acetonitrile (UZULUZ) have also been reported. In addition, LEN cocrystals and cocrystal hydrates have been reported with gallic acid (HUVGAI and HUVFUB; Song et al., 2015), 3,5-dihydroxybenzoic acid (XODPIR and XODPEN; Song et al., 2014), urea (XODPOX; Song et al., 2014), melamine (NUNSAU; Screen et al., 2025 ) and acesulfame (ZIDQUB and ZIDQUB01; Chen et al., 2019 ). Interestingly, one of the reported crystal structures contains protonated LEN, with a chloride ion (Cl⁻) serving as the counter-ion to maintain charge neutrality (VAGMEZ; Valdivia-Berroeta et al., 2021 ). However, to the best of our knowledge, no crystal structure of a LEN:RES has been reported to date.

6. Synthesis and crystallization

The LEN:RES cocrystal was prepared by a combination of liquid-assisted grinding and slow-evaporation crystallization. LEN (60 mg, 0.231 mmol) and RES (25.5 mg, 0.231 mmol) were taken in a 1:1 molar ratio and manually ground together in a mortar and pestle for approximately 10 min in the presence of a few drops of a 1:1 (v/v) acetone-ethanol solvent mixture. The resulting solid was subsequently dissolved in 1:1:1:1 (v/v/v/v) mixture of isopropyl alcohol, methanol, acetonitrile, and water and gently heated to ensure complete dissolution. The resulting solution was filtered to remove any undissolved material and transferred to a crystallization vessel. The solvent was allowed to evaporate slowly at room temperature (298 K). After 4–5 days, yellow, plate-like crystals suitable for single-crystal X-ray diffraction analysis were obtained.

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. All H atoms were placed in geometrically idealized positions. The H atoms attached to O4 and O5 were located in difference-Fourier maps and refined isotropically. The H atom attached to N3 was placed in a geometrically idealized position and the N3—H3 bond length was restrained to 0.95 Å using a DFIX restraint.

Table 2
Experimental details

Crystal data
Chemical formula	2C₁₃H₁₃N₃O₃·C₆H₆O₂
M_r	628.63
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	297
a, b, c (Å)	7.0508 (3), 14.1141 (6), 16.3951 (9)
α, β, γ (°)	110.596 (2), 100.956 (2), 101.880 (2)
V (Å³)	1431.91 (12)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.11
Crystal size (mm)	0.14 × 0.09 × 0.04

Data collection
Diffractometer	Bruker D8 VENTURE Kappa Duo PHOTON II CPAD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.632, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	44385, 7160, 3351
R_int	0.138
(sin θ/λ)_max (Å⁻¹)	0.671

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.168, 0.99
No. of reflections	7160
No. of parameters	439
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)	0.30, −0.26
Computer programs: APEX3 and SAINT (Bruker, 2016 ), SHELXS97 (Sheldrick, 2008 ), SHELXL2014/7 (Sheldrick, 2015 ), ORTEP-3 for Windows (Farrugia, 2012 ), Mercury (Macrae et al., 2020 ), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2020 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 2598460

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S205698902601114X/dx2074sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698902601114X/dx2074Isup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S205698902601114X/dx2074Isup3.cml

checkCIF report

Computing details top

3-(4-Amino-1-oxo-1,3-dihydro-2H-isoindol-2-yl)piperidine-2,6-dione–benzene-1,3-diol (2/1) top

Crystal data top

2C₁₃H₁₃N₃O₃·C₆H₆O₂	Z = 2
M_r = 628.63	F(000) = 660
Triclinic, P1	D_x = 1.458 Mg m⁻³
a = 7.0508 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.1141 (6) Å	Cell parameters from 7164 reflections
c = 16.3951 (9) Å	θ = 2.5–28.5°
α = 110.596 (2)°	µ = 0.11 mm⁻¹
β = 100.956 (2)°	T = 297 K
γ = 101.880 (2)°	Plate, pale yellow
V = 1431.91 (12) Å³	0.14 × 0.09 × 0.04 mm

Data collection top

Bruker D8 VENTURE Kappa Duo PHOTON II CPAD diffractometer	7160 independent reflections
Radiation source: micro-focus sealed tube, Incoatech IµS HB	3351 reflections with I > 2σ(I)
Multilayer mirrors monochromator	R_int = 0.138
φ and ω scans	θ_max = 28.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −9→9
T_min = 0.632, T_max = 0.746	k = −18→18
44385 measured reflections	l = −21→21

Refinement top

Refinement on F²	1 restraint
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.061	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.168	w = 1/[σ²(F_o²) + (0.069P)²] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max = 0.001
7160 reflections	Δρ_max = 0.30 e Å⁻³
439 parameters	Δρ_min = −0.26 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.4392 (3)	1.21869 (13)	0.66753 (11)	0.0466 (5)
O2	0.1038 (3)	0.70701 (13)	0.37776 (11)	0.0471 (5)
O3	0.6444 (3)	0.96443 (14)	0.58963 (12)	0.0526 (5)
N1	0.4203 (3)	1.06732 (14)	0.69316 (12)	0.0335 (5)
N2	0.6294 (4)	1.08409 (19)	0.96980 (16)	0.0551 (7)
N3	0.3680 (3)	0.83778 (15)	0.48570 (14)	0.0373 (5)
C1	0.5573 (4)	1.14192 (17)	0.84840 (15)	0.0322 (6)
C2	0.5571 (3)	1.22231 (18)	0.81917 (16)	0.0331 (6)
C3	0.6287 (4)	1.32822 (18)	0.87877 (17)	0.0402 (6)
H3A	0.628058	1.382037	0.858556	0.048*
C4	0.7014 (4)	1.34981 (19)	0.97012 (17)	0.0442 (7)
H4	0.750506	1.419965	1.012339	0.053*
C5	0.7028 (4)	1.27023 (19)	0.99993 (16)	0.0401 (6)
H5	0.753498	1.288036	1.061774	0.048*
C6	0.6302 (4)	1.16338 (19)	0.93995 (16)	0.0356 (6)
C7	0.4697 (4)	1.03661 (17)	0.76899 (15)	0.0340 (6)
H7A	0.567555	0.997243	0.762260	0.041*
H7B	0.349737	0.994421	0.774725	0.041*
C8	0.4685 (4)	1.17463 (18)	0.71944 (16)	0.0341 (6)
C9	0.3236 (4)	0.99346 (18)	0.60035 (15)	0.0335 (6)
H9	0.299217	1.035799	0.565413	0.040*
C10	0.1187 (4)	0.91915 (19)	0.58530 (16)	0.0385 (6)
H10A	0.134266	0.876290	0.619736	0.046*
H10B	0.029641	0.960111	0.606562	0.046*
C11	0.0268 (4)	0.84802 (19)	0.48517 (17)	0.0416 (6)
H11A	−0.097317	0.796450	0.477254	0.050*
H11B	−0.007630	0.890553	0.452601	0.050*
C12	0.1649 (4)	0.79088 (19)	0.44478 (16)	0.0346 (6)
C13	0.4619 (4)	0.93194 (18)	0.56100 (16)	0.0345 (6)
H3	0.443 (4)	0.8010 (18)	0.4577 (16)	0.052*
H2A	0.670 (4)	1.100 (2)	1.0250 (19)	0.052*
H2B	0.592 (4)	1.026 (2)	0.9329 (18)	0.052*
O4	1.2550 (3)	0.3382 (2)	0.38207 (14)	0.0767 (7)
O5	0.6176 (3)	0.16702 (16)	0.16464 (13)	0.0563 (6)
C14	1.0483 (4)	0.3148 (2)	0.36367 (19)	0.0481 (7)
C15	0.9331 (4)	0.2529 (2)	0.27456 (18)	0.0470 (7)
H15	0.995148	0.228355	0.229379	0.056*
C16	0.7265 (4)	0.22825 (19)	0.25380 (17)	0.0400 (6)
C17	0.6315 (4)	0.2623 (2)	0.32043 (18)	0.0447 (7)
H17	0.491186	0.243909	0.306246	0.054*
C18	0.7511 (5)	0.3246 (2)	0.40876 (18)	0.0484 (7)
H18	0.689303	0.348195	0.454229	0.058*
C19	0.9582 (5)	0.3523 (2)	0.43099 (17)	0.0469 (7)
H19	1.036325	0.395666	0.490416	0.056*
H1	1.308 (5)	0.359 (2)	0.444 (2)	0.070*
H5A	0.494 (5)	0.166 (2)	0.152 (2)	0.070*
O6	0.2332 (3)	0.17291 (13)	0.11279 (11)	0.0478 (5)
O7	0.0550 (3)	0.46102 (15)	0.18180 (13)	0.0553 (5)
O8	0.5573 (3)	0.63971 (15)	0.44179 (12)	0.0543 (5)
N4	0.2641 (3)	0.32938 (14)	0.09561 (13)	0.0360 (5)
N5	0.1058 (4)	0.3344 (2)	−0.17610 (17)	0.0524 (7)
N6	0.3138 (3)	0.55180 (16)	0.30871 (14)	0.0415 (6)
C20	0.1513 (4)	0.26472 (18)	−0.06018 (16)	0.0337 (6)
C21	0.0881 (4)	0.24901 (19)	−0.15121 (16)	0.0375 (6)
C22	0.0140 (4)	0.1445 (2)	−0.21483 (17)	0.0454 (7)
H22	−0.029956	0.130577	−0.276211	0.054*
C23	0.0040 (4)	0.0602 (2)	−0.18903 (18)	0.0482 (7)
H23	−0.047229	−0.008665	−0.233698	0.058*
C24	0.0678 (4)	0.07543 (19)	−0.09901 (17)	0.0434 (7)
H24	0.062888	0.019145	−0.081646	0.052*
C25	0.1398 (4)	0.18046 (18)	−0.03610 (16)	0.0345 (6)
C26	0.2149 (4)	0.22211 (18)	0.06352 (17)	0.0351 (6)
C27	0.2335 (4)	0.36639 (18)	0.02291 (15)	0.0369 (6)
H27A	0.359950	0.409290	0.022747	0.044*
H27B	0.137622	0.407037	0.028206	0.044*
C28	0.3475 (4)	0.39755 (18)	0.19125 (16)	0.0352 (6)
H28	0.340619	0.351277	0.223981	0.042*
C29	0.2221 (4)	0.47085 (19)	0.22422 (16)	0.0358 (6)
C30	0.5058 (4)	0.57531 (18)	0.36249 (17)	0.0389 (6)
C31	0.6447 (4)	0.5217 (2)	0.32072 (17)	0.0452 (7)
H31A	0.670477	0.472816	0.347679	0.054*
H31B	0.772645	0.574642	0.335705	0.054*
C32	0.5682 (4)	0.46140 (19)	0.21851 (17)	0.0419 (6)
H32A	0.648126	0.414196	0.198385	0.050*
H32B	0.581853	0.510698	0.189556	0.050*
H1C	0.079 (5)	0.388 (2)	−0.1394 (19)	0.063*
H1D	0.046 (4)	0.315 (2)	−0.2365 (19)	0.063*
H6	0.241 (4)	0.596 (2)	0.3330 (19)	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0613 (13)	0.0413 (10)	0.0367 (11)	0.0153 (9)	0.0107 (10)	0.0169 (9)
O2	0.0483 (12)	0.0406 (10)	0.0319 (10)	0.0099 (9)	0.0041 (9)	−0.0029 (9)
O3	0.0350 (12)	0.0613 (12)	0.0403 (11)	0.0071 (10)	0.0090 (10)	0.0015 (10)
N1	0.0424 (13)	0.0300 (10)	0.0210 (11)	0.0069 (9)	0.0071 (10)	0.0054 (9)
N2	0.083 (2)	0.0437 (14)	0.0260 (14)	0.0064 (14)	0.0098 (15)	0.0093 (13)
N3	0.0346 (13)	0.0359 (11)	0.0312 (12)	0.0108 (10)	0.0107 (10)	0.0009 (10)
C1	0.0339 (14)	0.0323 (13)	0.0257 (13)	0.0064 (11)	0.0114 (11)	0.0070 (11)
C2	0.0279 (14)	0.0361 (13)	0.0307 (14)	0.0080 (11)	0.0096 (11)	0.0086 (12)
C3	0.0431 (16)	0.0291 (13)	0.0390 (16)	0.0075 (12)	0.0106 (13)	0.0055 (13)
C4	0.0427 (17)	0.0335 (14)	0.0363 (16)	0.0059 (12)	0.0076 (13)	−0.0035 (13)
C5	0.0383 (16)	0.0432 (15)	0.0241 (14)	0.0057 (12)	0.0069 (12)	0.0014 (12)
C6	0.0322 (15)	0.0402 (14)	0.0281 (14)	0.0067 (11)	0.0090 (12)	0.0086 (12)
C7	0.0400 (15)	0.0316 (12)	0.0281 (13)	0.0086 (11)	0.0109 (12)	0.0099 (11)
C8	0.0353 (15)	0.0329 (13)	0.0312 (14)	0.0086 (11)	0.0127 (12)	0.0090 (12)
C9	0.0388 (15)	0.0338 (12)	0.0196 (12)	0.0091 (11)	0.0065 (11)	0.0035 (11)
C10	0.0381 (16)	0.0380 (13)	0.0330 (15)	0.0132 (12)	0.0124 (12)	0.0049 (12)
C11	0.0368 (16)	0.0415 (14)	0.0351 (15)	0.0111 (12)	0.0047 (13)	0.0057 (13)
C12	0.0388 (16)	0.0370 (13)	0.0238 (13)	0.0114 (12)	0.0057 (12)	0.0090 (12)
C13	0.0366 (16)	0.0369 (13)	0.0257 (14)	0.0083 (12)	0.0099 (12)	0.0088 (12)
O4	0.0509 (15)	0.124 (2)	0.0492 (14)	0.0202 (14)	0.0114 (12)	0.0327 (16)
O5	0.0605 (14)	0.0674 (13)	0.0331 (11)	0.0222 (12)	0.0059 (11)	0.0138 (10)
C14	0.0446 (19)	0.0634 (18)	0.0416 (17)	0.0173 (15)	0.0120 (14)	0.0270 (15)
C15	0.0532 (19)	0.0627 (18)	0.0337 (16)	0.0231 (15)	0.0189 (14)	0.0227 (15)
C16	0.0535 (19)	0.0380 (14)	0.0285 (15)	0.0154 (13)	0.0083 (13)	0.0143 (13)
C17	0.0451 (17)	0.0528 (16)	0.0412 (17)	0.0194 (14)	0.0127 (14)	0.0219 (15)
C18	0.060 (2)	0.0560 (17)	0.0375 (17)	0.0286 (16)	0.0190 (15)	0.0192 (15)
C19	0.058 (2)	0.0485 (16)	0.0310 (15)	0.0176 (15)	0.0085 (14)	0.0141 (14)
O6	0.0598 (13)	0.0374 (10)	0.0392 (11)	0.0099 (9)	0.0066 (10)	0.0142 (9)
O7	0.0385 (12)	0.0613 (12)	0.0441 (12)	0.0148 (10)	0.0013 (10)	0.0015 (10)
O8	0.0590 (13)	0.0559 (12)	0.0278 (10)	0.0140 (10)	0.0012 (10)	0.0016 (10)
N4	0.0430 (13)	0.0301 (11)	0.0250 (11)	0.0077 (10)	0.0048 (10)	0.0043 (10)
N5	0.0626 (18)	0.0578 (16)	0.0342 (14)	0.0182 (14)	0.0108 (13)	0.0170 (14)
N6	0.0377 (14)	0.0402 (12)	0.0324 (13)	0.0130 (10)	0.0031 (11)	0.0013 (11)
C20	0.0294 (14)	0.0374 (13)	0.0269 (14)	0.0094 (11)	0.0063 (11)	0.0058 (12)
C21	0.0313 (15)	0.0440 (15)	0.0297 (14)	0.0094 (12)	0.0084 (12)	0.0075 (13)
C22	0.0388 (16)	0.0566 (17)	0.0276 (15)	0.0112 (14)	0.0074 (13)	0.0048 (14)
C23	0.0423 (17)	0.0411 (15)	0.0350 (16)	0.0042 (13)	0.0086 (14)	−0.0084 (13)
C24	0.0436 (17)	0.0355 (14)	0.0389 (16)	0.0108 (12)	0.0096 (14)	0.0029 (13)
C25	0.0329 (15)	0.0357 (13)	0.0278 (14)	0.0091 (11)	0.0086 (12)	0.0053 (12)
C26	0.0343 (15)	0.0317 (13)	0.0362 (15)	0.0082 (11)	0.0099 (12)	0.0114 (13)
C27	0.0375 (15)	0.0351 (13)	0.0325 (14)	0.0088 (12)	0.0086 (12)	0.0091 (12)
C28	0.0416 (16)	0.0311 (12)	0.0255 (13)	0.0098 (12)	0.0052 (12)	0.0058 (11)
C29	0.0325 (16)	0.0374 (14)	0.0280 (14)	0.0058 (12)	0.0043 (12)	0.0072 (12)
C30	0.0448 (17)	0.0328 (13)	0.0305 (15)	0.0068 (12)	0.0051 (13)	0.0087 (13)
C31	0.0360 (16)	0.0429 (15)	0.0395 (16)	0.0068 (12)	0.0040 (13)	0.0034 (13)
C32	0.0346 (15)	0.0412 (14)	0.0381 (16)	0.0100 (12)	0.0051 (13)	0.0061 (13)

Geometric parameters (Å, º) top

O1—C8	1.230 (3)	C15—C16	1.371 (4)
O2—C12	1.220 (3)	C16—C17	1.384 (3)
O3—C13	1.209 (3)	C17—C18	1.384 (4)
N1—C8	1.367 (3)	C18—C19	1.371 (4)
N1—C9	1.437 (3)	O6—C26	1.242 (3)
N1—C7	1.460 (3)	O7—C29	1.202 (3)
N2—C6	1.370 (3)	O8—C30	1.225 (3)
N3—C12	1.368 (3)	N4—C26	1.358 (3)
N3—C13	1.379 (3)	N4—C28	1.444 (3)
C1—C2	1.378 (3)	N4—C27	1.458 (3)
C1—C6	1.390 (3)	N5—C21	1.392 (3)
C1—C7	1.497 (3)	N6—C30	1.370 (3)
C2—C3	1.385 (3)	N6—C29	1.373 (3)
C2—C8	1.477 (3)	C20—C25	1.371 (3)
C3—C4	1.386 (3)	C20—C21	1.396 (3)
C4—C5	1.375 (3)	C20—C27	1.494 (3)
C5—C6	1.397 (3)	C21—C22	1.389 (3)
C9—C10	1.519 (3)	C22—C23	1.390 (4)
C9—C13	1.522 (3)	C23—C24	1.382 (4)
C10—C11	1.514 (3)	C24—C25	1.391 (3)
C11—C12	1.493 (3)	C25—C26	1.470 (3)
O4—C14	1.375 (3)	C28—C29	1.519 (3)
O5—C16	1.373 (3)	C28—C32	1.519 (3)
C14—C19	1.377 (4)	C30—C31	1.482 (3)
C14—C15	1.384 (4)	C31—C32	1.513 (3)

C8—N1—C9	122.6 (2)	C15—C16—C17	121.2 (3)
C8—N1—C7	113.20 (19)	O5—C16—C17	121.4 (3)
C9—N1—C7	124.16 (18)	C16—C17—C18	118.2 (3)
C12—N3—C13	127.7 (2)	C19—C18—C17	121.7 (3)
C2—C1—C6	121.4 (2)	C18—C19—C14	118.7 (3)
C2—C1—C7	109.99 (19)	C26—N4—C28	122.7 (2)
C6—C1—C7	128.6 (2)	C26—N4—C27	112.5 (2)
C1—C2—C3	122.2 (2)	C28—N4—C27	124.77 (18)
C1—C2—C8	108.6 (2)	C30—N6—C29	127.0 (2)
C3—C2—C8	129.2 (2)	C25—C20—C21	121.0 (2)
C2—C3—C4	116.5 (2)	C25—C20—C27	110.0 (2)
C5—C4—C3	121.7 (2)	C21—C20—C27	129.0 (2)
C4—C5—C6	121.8 (2)	C22—C21—N5	122.4 (2)
N2—C6—C1	121.8 (2)	C22—C21—C20	116.5 (2)
N2—C6—C5	121.8 (2)	N5—C21—C20	121.1 (2)
C1—C6—C5	116.3 (2)	C21—C22—C23	121.6 (2)
N1—C7—C1	102.00 (18)	C24—C23—C22	122.0 (2)
O1—C8—N1	124.7 (2)	C23—C24—C25	115.6 (3)
O1—C8—C2	129.1 (2)	C20—C25—C24	123.2 (2)
N1—C8—C2	106.2 (2)	C20—C25—C26	108.2 (2)
N1—C9—C10	114.20 (18)	C24—C25—C26	128.6 (2)
N1—C9—C13	111.7 (2)	O6—C26—N4	123.9 (2)
C10—C9—C13	111.10 (19)	O6—C26—C25	129.0 (2)
C11—C10—C9	109.87 (19)	N4—C26—C25	107.1 (2)
C12—C11—C10	113.0 (2)	N4—C27—C20	102.16 (18)
O2—C12—N3	120.2 (2)	N4—C28—C29	112.0 (2)
O2—C12—C11	123.0 (2)	N4—C28—C32	114.32 (19)
N3—C12—C11	116.8 (2)	C29—C28—C32	109.95 (19)
O3—C13—N3	120.5 (2)	O7—C29—N6	120.8 (2)
O3—C13—C9	123.3 (2)	O7—C29—C28	124.4 (2)
N3—C13—C9	116.1 (2)	N6—C29—C28	114.8 (2)
O4—C14—C19	121.5 (3)	O8—C30—N6	119.8 (2)
O4—C14—C15	117.6 (2)	O8—C30—C31	122.6 (2)
C19—C14—C15	120.9 (3)	N6—C30—C31	117.6 (2)
C16—C15—C14	119.1 (2)	C30—C31—C32	114.8 (2)
C15—C16—O5	117.4 (2)	C31—C32—C28	109.7 (2)

C6—C1—C2—C3	0.0 (4)	O5—C16—C17—C18	−179.5 (2)
C7—C1—C2—C3	179.5 (2)	C16—C17—C18—C19	−0.2 (4)
C6—C1—C2—C8	−179.2 (2)	C17—C18—C19—C14	−1.6 (4)
C7—C1—C2—C8	0.4 (3)	O4—C14—C19—C18	−178.7 (2)
C1—C2—C3—C4	0.0 (4)	C15—C14—C19—C18	2.0 (4)
C8—C2—C3—C4	179.0 (2)	C25—C20—C21—C22	0.0 (3)
C2—C3—C4—C5	0.2 (4)	C27—C20—C21—C22	−178.8 (2)
C3—C4—C5—C6	−0.3 (4)	C25—C20—C21—N5	−177.9 (2)
C2—C1—C6—N2	179.4 (2)	C27—C20—C21—N5	3.3 (4)
C7—C1—C6—N2	−0.1 (4)	N5—C21—C22—C23	177.7 (2)
C2—C1—C6—C5	−0.1 (3)	C20—C21—C22—C23	−0.2 (4)
C7—C1—C6—C5	−179.6 (2)	C21—C22—C23—C24	−0.3 (4)
C4—C5—C6—N2	−179.2 (2)	C22—C23—C24—C25	0.9 (4)
C4—C5—C6—C1	0.3 (4)	C21—C20—C25—C24	0.6 (4)
C8—N1—C7—C1	0.1 (2)	C27—C20—C25—C24	179.7 (2)
C9—N1—C7—C1	−177.6 (2)	C21—C20—C25—C26	−179.5 (2)
C2—C1—C7—N1	−0.3 (2)	C27—C20—C25—C26	−0.4 (3)
C6—C1—C7—N1	179.2 (2)	C23—C24—C25—C20	−1.0 (4)
C9—N1—C8—O1	−1.6 (4)	C23—C24—C25—C26	179.1 (2)
C7—N1—C8—O1	−179.4 (2)	C28—N4—C26—O6	1.3 (4)
C9—N1—C8—C2	177.9 (2)	C27—N4—C26—O6	178.2 (2)
C7—N1—C8—C2	0.1 (3)	C28—N4—C26—C25	−178.7 (2)
C1—C2—C8—O1	179.2 (2)	C27—N4—C26—C25	−1.9 (3)
C3—C2—C8—O1	0.1 (4)	C20—C25—C26—O6	−178.7 (2)
C1—C2—C8—N1	−0.3 (3)	C24—C25—C26—O6	1.2 (4)
C3—C2—C8—N1	−179.4 (2)	C20—C25—C26—N4	1.4 (3)
C8—N1—C9—C10	−119.2 (2)	C24—C25—C26—N4	−178.7 (2)
C7—N1—C9—C10	58.3 (3)	C26—N4—C27—C20	1.6 (3)
C8—N1—C9—C13	113.7 (2)	C28—N4—C27—C20	178.4 (2)
C7—N1—C9—C13	−68.8 (3)	C25—C20—C27—N4	−0.7 (3)
N1—C9—C10—C11	177.73 (19)	C21—C20—C27—N4	178.3 (2)
C13—C9—C10—C11	−54.9 (3)	C26—N4—C28—C29	−124.1 (2)
C9—C10—C11—C12	53.1 (3)	C27—N4—C28—C29	59.5 (3)
C13—N3—C12—O2	179.7 (2)	C26—N4—C28—C32	110.0 (3)
C13—N3—C12—C11	0.6 (4)	C27—N4—C28—C32	−66.5 (3)
C10—C11—C12—O2	154.8 (2)	C30—N6—C29—O7	−176.8 (2)
C10—C11—C12—N3	−26.2 (3)	C30—N6—C29—C28	3.6 (3)
C12—N3—C13—O3	−179.5 (2)	N4—C28—C29—O7	13.1 (3)
C12—N3—C13—C9	−3.2 (3)	C32—C28—C29—O7	141.4 (2)
N1—C9—C13—O3	−24.3 (3)	N4—C28—C29—N6	−167.24 (19)
C10—C9—C13—O3	−153.0 (2)	C32—C28—C29—N6	−39.0 (3)
N1—C9—C13—N3	159.58 (19)	C29—N6—C30—O8	−169.0 (2)
C10—C9—C13—N3	30.8 (3)	C29—N6—C30—C31	11.9 (4)
O4—C14—C15—C16	−179.9 (2)	O8—C30—C31—C32	−168.9 (2)
C19—C14—C15—C16	−0.6 (4)	N6—C30—C31—C32	10.2 (3)
C14—C15—C16—O5	179.8 (2)	C30—C31—C32—C28	−44.5 (3)
C14—C15—C16—C17	−1.3 (4)	N4—C28—C32—C31	−174.74 (19)
C15—C16—C17—C18	1.6 (4)	C29—C28—C32—C31	58.3 (3)

Hydrogen-bond geometry (Å, º) top

Ring centroids are defined as: Cg1 = N1/C7/C1/C2/C8; Cg2 = N3/C9–C13; Cg3 = C1–C6;Cg5 = N4/C20/C25–C27; Cg6 = N6/C28–C32; Cg7 = C20–C25; and Cg9 = C14–C19. Cg···Cg denotes the centroid—centroid distance associated with π–π interactions.

D—H···A	D—H	H···A	D···A	D—H···A
O4—H1···O8ⁱ	0.93 (3)	1.92 (3)	2.816 (3)	161 (3)
O5—H5A···O6	0.85 (3)	1.87 (3)	2.710 (3)	171 (3)
N2—H2B···O5ⁱⁱ	0.78 (3)	2.56 (3)	3.310 (3)	163 (3)
N2—H2A···O5ⁱⁱⁱ	0.83 (3)	2.28 (3)	3.015 (3)	148 (3)
N3—H3···O1^iv	0.89 (2)	2.31 (2)	3.022 (3)	137 (2)
N3—H3···O8	0.89 (2)	2.51 (2)	3.256 (3)	141 (2)
N5—H1D···O2^v	0.92 (3)	2.23 (3)	3.144 (3)	172 (2)
N6—H6···O2	0.92 (3)	2.00 (3)	2.915 (3)	171 (2)
C9—H9···O3^iv	0.98	2.65	3.409 (3)	135
C17—H17···O4^vi	0.93	2.57	3.263 (3)	131
C27—H27B···O7	0.97	2.58	3.106 (3)	114
C31—H31B···O2^vii	0.97	2.47	3.440 (3)	178
C10—H10A···Cg9ⁱⁱ		2.65	3.581 (3)	161
Cg1···Cg7ⁱⁱⁱ			3.7109 (16)
Cg1···Cg7^viii			4.0014 (17)
Cg3···Cg5ⁱⁱⁱ			3.7997 (17)
Cg3···Cg5^viii			3.9603 (17)
Cg3···Cg7ⁱⁱⁱ			3.6971 (17)
Cg3···Cg7^viii			3.6644 (17)
Cg3···Cg8ⁱⁱⁱ			3.5854 (15)
Cg3···Cg8^viii			3.6382 (15)
Cg4···Cg7ⁱⁱⁱ			3.5410 (15)
Cg4···Cg7^viii			3.6602 (15)
Cg4···Cg8ⁱⁱⁱ			3.6763 (13)
Cg4···Cg8^viii			3.8723 (13)

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

Funding information

This work was supported by the CSIR-National Laboratories Scheme under the NCL-CAI (MLP002629).

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