A new triclinic polymorph of 6,6′-{(1E,1E′)-[(1,2-di­phenyl­ethane-1,2-di­yl)bis­(aza­neylyl­idene)]bis­(methane­ylyl­idene)}bis­(2-chloro­phenol)

Iwatani, M.; Nakane, D.; Akitsu, T.

doi:10.1107/S2056989025008850

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Volume 81| Part 11| November 2025| Pages 1023-1027

https://doi.org/10.1107/S2056989025008850

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A new triclinic polymorph of 6,6′-{(1E,1E′)-[(1,2-diphenylethane-1,2-diyl)bis(azaneylylidene)]bis(methaneylylidene)}bis(2-chlorophenol)

Marika Iwatani,^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: [email protected]

Edited by Y. Ozawa, University of Hyogo, Japan (Received 9 September 2025; accepted 11 October 2025; online 17 October 2025)

The redetermined structure of a new polymorph of 6,6′-{(1E,1E′)-[(1,2-diphenylethane-1,2-diyl)bis(azaneylylidene)]bis(methaneylylidene)}bis(2-chlorophenol), C₂₈H₂₂Cl₂N₂O₂ was reported. The title compound was synthesized under microwave irradiation at 90 K, within 10 min. The asymmetric unit comprises a potentially tetradentate Schiff base ligand that crystallizes in the triclinic system with space group P1. The structure displays intramolecular O—H⋯N hydrogen bonding, forming an S(6) ring. Comparisons are made with the monoclinic polymorph [Shen et al. (2017). RSC Adv. 7, 40640–40649].

Keywords: crystal structure; polymorph; salen-type compound; intramolecular hydrogen bonding.

CCDC reference: 2494676

1. Chemical context

Schiff base complexes have played a central role in the development of coordination chemistry, as evidenced by their vast number, ease and flexibility of synthetic procedures, diverse properties, and applications as bioactive compounds such as antitumor, antibacterial, antifungal, and various other biological applications. Numerous reports have shown that salen-type metal complexes exhibit high activity against various diseases, including cancer (Nworie et al., 2016 ). Polymorphism is known to exist in crystals of Schiff base complex ligands and, as reported by Suda et al. (2021 ), in particular the angle of the phenyl group bonded to the nitrogen atom was different from that previously reported. Salen-type compounds are synthesized from diamines and salicylaldehyde and contain two azomethine groups that are used as organic ligands in complex formation (Akitsu et al., 2011 ). In our laboratory, we have been studying salen-type metal complexes, which have the potential to be useful in a variety of applications, including as a new concept dye for dye-sensitized solar cells (DSSC), flame retardant in heat-stabilized PVC sheets and artificial metalloenzymes that mimic the catalytic efficiency of natural metalloenzymes (Yamane et al., 2017 ; Soni et al., 2020 ; Kashiwagi et al., 2019 ). Salen-type metal complexes are known to exhibit ligand disorder (Akitsu et al., 2005b ). However, there are also examples of non-disordered salen-type metal complexes (Akitsu et al., 2005a ). In this report, we describe a new polymorphic crystal structure of the title compound.

2. Structural commentary

The title compound (Fig. 1) crystallizes in the triclinic system with P $[\overline{1}]$ space group. The crystals obtained were racemic, with one molecule being an RR isomer (optically active). The previously reported crystal was monoclinic, had a space group of I2/a, and was colorless and transparent (Shen et al., 2017 ). Intramolecular hydrogen bonds with an S(6) (Bernstein et al., 1995 ) ring formation are observed, with O⋯N distances of 2.564 (3) and 2.597 (3) Å (Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O29—H29⋯N31	0.84	1.82	2.564 (3)	147
O30—H30⋯N32	0.84	1.85	2.597 (3)	147

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

Comparing the bond distances, bond angles, and torsion angles with monoclinic polymorph the bond distances and bond angles are almost the same, but there are significant differences in the torsion angles. The torsion angles C6—C7—N31—C22 and C9—C8—N32—C15 are −22.8 (3) and −105.8 (2)°, respectively, in the title compound compared 108.3 (2)° in the monoclinic polymorph. In the title compound, N32—C8—C7—N31 is −50.7 (2)° [43.3 (2) and −42.6 (2)° in the monoclinic polymorph] while N32—C8—C9—C14 and N31—C7—C6—C1 are −60.7 (3) and −72.1 (3)°, respectively [43.2 (2) and −85.8 (2)° in the monoclinic polymorph].

3. Supramolecular features

No intermolecular hydrogen bonds are observed in the crystal, but a Cl⋯Cl halogen interaction with length of 3.4122 (11) Å is found. There are two molecules in the unit cell. In contrast, the unit cell of the monoclinic polymorph contains 12 molecules, with an intermolecular O⋯Cl hydrogen bond of 3.176 Å in length, weak O⋯H interactions (2.688 and 2.570 Å) and a C⋯Cl interaction (3.225 Å; Shen et al., 2017). An interesting feature of the crystal packing (Figs. 2–4 ) of the title compound is the presence of centrosymmetric Cl33⋯Cl34 [3.4122 (11) Å] and n⋯π^* (Echeverriá et al., 2018 ) [O30⋯C22 = 3.029 (3) Å] interactions, which are shorter than sum of the van der Waals radii of the involved atoms (Bondi et al., 1964 ). These interactions are supported by a short C4⋯C19 [3.361 (3) Å] contact, forming a one-dimensional extended chain of neighboring molecules parallel to the bc-plane.

Figure 2
Packing of the title compound, viewed along the b-axis direction.

Figure 3
Packing of the title compound viewed along the a-axis direction.

Figure 4
The packing of the title compound, showing the chain formed by Cl⋯Cl and O⋯C contacts.

A Hirshfeld surface analysis (McKinnon et al., 2004 ) was performed to further investigate the intermolecular interactions and contacts using Crystal Explorer 17.5 (McKinnon et al., 2007 ; Turner et al., 2017 ) (Fig. 5). It indicates that the most important contributions to the packing are from H⋯H (35.2%), C⋯H/H⋯C (18.4%) and Cl⋯H/H⋯Cl (10.3%) contacts. The intermolecular C—H⋯C hydrogen bonds are indicated by bright-red spots 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) < 2.4 Å in the 2D finger plots (Fig. 3).

Figure 5
Hirshfeld surface mapped over d_norm and the two-dimensional fingerprint plots.

The contributions to the packing from H⋯H, C⋯C, C⋯H/H⋯C, Cl⋯H/H⋯Cl, N⋯H/H⋯N, and H⋯O/O⋯H contacts are 35.2, 1.7, 33.0, 16.5, 1.4 and 8.6%, respectively. The structure is characterized by a high proportion of H⋯H interactions, which are van der Waals interactions. The high C⋯H/H⋯C value is due to the presence of aromatic rings in the compound. The low C⋯C value is due to the lack of overlapping aromatic rings in the structure.

4. Database survey

A search in the Cambridge Structural Database (CSD, Version 5.41, update of January 2024; Groom et al. 2016 ) for similar structures gave 6,6′-{(1E,1E′)-[(1,2-diphenylethane-1,2-diyl)bis(azaneylylidene)]bis(methaneylylidene)}bis(2-fluorophenol), which is the monoclinic polymorph (refcode LECYUQ; Shen et al., 2017). Besides this, there are several similar compounds, such as 6,6′-((1E,1E′)-{[(1R,2R)-1,2-diphenylethane-1,2-diyl]bis(azanylylidene)}bis(methanylylidene))bis(2-ethylphenol) (refcode OWIJAI; Xu et al., 2021 ) and N,N-sisalicylidene-(R,S)(S,R)-1,2-ethanediamine (refcode DSPEDN01; Ramazani et al., 2006 ).

5. Synthesis and crystallization

3-Chlorosalicylaldehyde (0.039 g, 0.25 mmol) and racemic-(+/-)-1,2-diphenylethylenediamine (0.027 g, 0.125 mmol) were dissolved in 18 mL of methanol. The solution was stirred 50 s and irradiated with microwaves for 10 minutes at 353 K. The resulting clear yellow solution was evaporated. Recrystallized by slow evaporation of diethyl ether solution gave clear yellow rectangular-parallelepiped-shaped single crystals suitable for single-crystal X-ray diffraction analysis within a day. IR (ATR, cm ⁻¹): 522 (s), 776 (m), 832 (w), 896 (s), 1093 (m, C—OH), 1413 (w), 1447 (w), 1624 (m, C=N)

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 = 0.95–0.10 Å) and were refined 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 O-bound H atoms H29, H30 were located based on a difference-Fourier map and refined using constraints. In the process of removing the weak reciprocal lattice points due to twins, some reflections that should be present may have been inadvertently deleted.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₈H₂₂Cl₂N₂O₂
M_r	489.37
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	90
a, b, c (Å)	9.8543 (15), 11.1140 (17), 11.4288 (18)
α, β, γ (°)	86.563 (5), 74.417 (5), 82.951 (5)
V (Å³)	1196.1 (3)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.30
Crystal size (mm)	0.80 × 0.30 × 0.30

Data collection
Diffractometer	Bruker D8 QUEST
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.70, 0.92
No. of measured, independent and observed [I > 2σ(I)] reflections	7500, 2909, 2808
R_int	0.057
θ_max (°)	22.4
(sin θ/λ)_max (Å⁻¹)	0.536

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.078, 0.178, 1.14
No. of reflections	2909
No. of parameters	309
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.78, −0.56
Computer programs: APEX4 and SAINT (Bruker, 2019 ), SHELXT2018/2 (Sheldrick, 2015a ), SHELXL2019/1 (Sheldrick, 2015b ) and shelXle ShelXle (Hübschle et al., 2011 ).

Supporting information

CCDC reference: 2494676

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2056989025008850/ox2018sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989025008850/ox2018Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989025008850/ox2018Isup3.cml

checkCIF report

Computing details top

6,6'-{(1E,1E')-[(1,2-Diphenylethane-1,2-diyl)bis(azaneylylidene)]bis(methaneylylidene)}bis(2-chlorophenol) top

Crystal data top

C₂₈H₂₂Cl₂N₂O₂	Z = 2
M_r = 489.37	F(000) = 508
Triclinic, P1	D_x = 1.359 Mg m⁻³
a = 9.8543 (15) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.1140 (17) Å	Cell parameters from 7076 reflections
c = 11.4288 (18) Å	θ = 2.6–22.4°
α = 86.563 (5)°	µ = 0.30 mm⁻¹
β = 74.417 (5)°	T = 90 K
γ = 82.951 (5)°	Plate, yellow
V = 1196.1 (3) Å³	0.80 × 0.30 × 0.30 mm

Data collection top

Bruker D8 QUEST diffractometer	2808 reflections with I > 2σ(I)
Detector resolution: 7.3910 pixels mm^-1	R_int = 0.057
φ and ω scans	θ_max = 22.4°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −10→10
T_min = 0.70, T_max = 0.92	k = −11→11
7500 measured reflections	l = −12→12
2909 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.078	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.178	w = 1/[σ²(F_o²) + (0.1181P)² + 0.4041P] where P = (F_o² + 2F_c²)/3
S = 1.14	(Δ/σ)_max < 0.001
2909 reflections	Δρ_max = 0.78 e Å⁻³
309 parameters	Δρ_min = −0.56 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
Cl33	0.69894 (7)	0.77330 (6)	0.10865 (5)	0.0321 (3)
Cl34	0.48781 (7)	0.21930 (6)	0.10402 (6)	0.0386 (3)
O29	0.70703 (17)	0.59076 (14)	0.30123 (15)	0.0236 (5)
H29	0.707911	0.541261	0.359594	0.068 (12)*
O30	0.58282 (17)	0.26535 (16)	0.31484 (15)	0.0267 (5)
H30	0.614604	0.279211	0.373340	0.066 (12)*
N31	0.72307 (19)	0.51873 (17)	0.51494 (17)	0.0183 (5)
N32	0.77316 (19)	0.28700 (16)	0.42902 (17)	0.0183 (5)
C1	0.9058 (3)	0.4613 (2)	0.7130 (2)	0.0220 (6)
H1	0.977177	0.452213	0.638356	0.026000*
C12	0.7867 (3)	−0.0137 (2)	0.7700 (2)	0.0238 (6)
H12	0.779742	−0.084463	0.821244	0.029000*
C13	0.6670 (3)	0.0463 (2)	0.7423 (2)	0.0234 (6)
H13	0.577598	0.016854	0.775207	0.028000*
C14	0.6770 (2)	0.1492 (2)	0.6668 (2)	0.0214 (6)
H14	0.594582	0.189105	0.647407	0.026000*
C15	0.8672 (2)	0.2710 (2)	0.3286 (2)	0.0179 (6)
H15	0.963560	0.274867	0.326773	0.021000*
C16	0.8330 (3)	0.24711 (19)	0.2164 (2)	0.0195 (6)
C17	0.9410 (3)	0.2246 (2)	0.1100 (2)	0.0264 (6)
H17	1.036817	0.227321	0.110552	0.032000*
C18	0.9104 (3)	0.1985 (2)	0.0043 (2)	0.0325 (7)
H18	0.984757	0.182025	−0.067299	0.039000*
C19	0.7710 (3)	0.1964 (2)	0.0027 (2)	0.0307 (7)
H19	0.749397	0.178877	−0.070156	0.037000*
C20	0.6632 (3)	0.2197 (2)	0.1067 (2)	0.0253 (6)
C21	0.6908 (3)	0.24488 (19)	0.2153 (2)	0.0207 (6)
C22	0.7105 (2)	0.6290 (2)	0.5464 (2)	0.0180 (6)
H22	0.705884	0.646557	0.627801	0.022000*
C23	0.7031 (2)	0.7283 (2)	0.4572 (2)	0.0174 (6)
C24	0.6948 (2)	0.8487 (2)	0.4918 (2)	0.0215 (6)
H24	0.691537	0.864924	0.573228	0.026000*
C25	0.6914 (2)	0.9436 (2)	0.4090 (2)	0.0236 (6)
H25	0.685739	1.024745	0.433281	0.028000*
C26	0.6962 (2)	0.9203 (2)	0.2899 (2)	0.0236 (6)
H26	0.695707	0.985296	0.232084	0.028000*
C27	0.7018 (2)	0.8019 (2)	0.2556 (2)	0.0216 (6)
C28	0.7046 (2)	0.7043 (2)	0.3380 (2)	0.0186 (6)
C2	0.9419 (3)	0.4896 (2)	0.8163 (2)	0.0248 (6)
H2	1.037668	0.498182	0.812667	0.030000*
C3	0.8383 (3)	0.5054 (2)	0.9247 (2)	0.0274 (6)
H3	0.862207	0.526466	0.995457	0.033000*
C4	0.6999 (3)	0.4904 (2)	0.9294 (2)	0.0304 (7)
H4	0.628617	0.500581	1.003883	0.036000*
C5	0.6643 (3)	0.4606 (2)	0.8265 (2)	0.0261 (6)
H5	0.568705	0.450108	0.831112	0.031000*
C6	0.7664 (2)	0.4459 (2)	0.7168 (2)	0.0185 (6)
C7	0.7240 (2)	0.4172 (2)	0.6047 (2)	0.0181 (6)
H7	0.625043	0.394426	0.632597	0.022000*
C8	0.8179 (2)	0.3074 (2)	0.5376 (2)	0.0167 (6)
H8	0.918827	0.325516	0.512654	0.020000*
C9	0.8068 (2)	0.1941 (2)	0.6193 (2)	0.0171 (6)
C10	0.9253 (3)	0.1342 (2)	0.6481 (2)	0.0236 (6)
H10	1.014514	0.164461	0.616680	0.028000*
C11	0.9160 (3)	0.0300 (2)	0.7228 (2)	0.0270 (6)
H11	0.998589	−0.010831	0.741072	0.032000*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl33	0.0450 (5)	0.0330 (5)	0.0197 (5)	−0.0019 (3)	−0.0125 (3)	0.0016 (3)
Cl34	0.0431 (5)	0.0379 (5)	0.0479 (6)	−0.0175 (4)	−0.0315 (4)	0.0108 (4)
O29	0.0337 (10)	0.0160 (9)	0.0221 (10)	−0.0004 (7)	−0.0094 (8)	−0.0029 (8)
O30	0.0221 (10)	0.0335 (11)	0.0255 (11)	−0.0067 (8)	−0.0072 (8)	0.0025 (8)
N31	0.0189 (10)	0.0160 (11)	0.0199 (11)	−0.0015 (8)	−0.0048 (9)	−0.0009 (8)
N32	0.0209 (11)	0.0132 (10)	0.0207 (11)	−0.0014 (8)	−0.0053 (9)	0.0002 (8)
C1	0.0250 (13)	0.0214 (13)	0.0189 (13)	−0.0035 (10)	−0.0039 (11)	−0.0020 (10)
C12	0.0317 (14)	0.0166 (13)	0.0244 (14)	−0.0037 (11)	−0.0098 (11)	0.0019 (10)
C13	0.0229 (13)	0.0196 (13)	0.0288 (14)	−0.0063 (10)	−0.0076 (11)	0.0008 (10)
C14	0.0198 (13)	0.0190 (13)	0.0270 (14)	−0.0017 (10)	−0.0090 (11)	−0.0009 (10)
C15	0.0178 (12)	0.0128 (12)	0.0218 (14)	−0.0009 (9)	−0.0035 (11)	−0.0004 (9)
C16	0.0263 (13)	0.0103 (12)	0.0221 (14)	−0.0002 (10)	−0.0075 (11)	0.0006 (9)
C17	0.0291 (14)	0.0243 (14)	0.0241 (15)	0.0036 (11)	−0.0067 (12)	−0.0030 (11)
C18	0.0443 (17)	0.0313 (15)	0.0205 (14)	0.0075 (12)	−0.0101 (12)	−0.0057 (11)
C19	0.0528 (18)	0.0196 (14)	0.0248 (15)	0.0010 (12)	−0.0204 (13)	−0.0040 (11)
C20	0.0388 (16)	0.0120 (12)	0.0311 (15)	−0.0058 (11)	−0.0191 (13)	0.0036 (10)
C21	0.0275 (14)	0.0094 (12)	0.0255 (14)	−0.0021 (10)	−0.0084 (11)	0.0029 (10)
C22	0.0150 (12)	0.0199 (13)	0.0184 (13)	−0.0014 (9)	−0.0031 (10)	−0.0027 (10)
C23	0.0126 (11)	0.0177 (12)	0.0205 (13)	0.0006 (9)	−0.0026 (10)	−0.0020 (10)
C24	0.0191 (13)	0.0194 (13)	0.0260 (14)	−0.0001 (10)	−0.0061 (10)	−0.0034 (10)
C25	0.0231 (13)	0.0164 (13)	0.0317 (15)	−0.0025 (10)	−0.0076 (11)	−0.0015 (10)
C26	0.0201 (12)	0.0187 (13)	0.0311 (15)	−0.0008 (10)	−0.0073 (11)	0.0058 (10)
C27	0.0183 (12)	0.0242 (14)	0.0220 (14)	−0.0007 (10)	−0.0059 (10)	0.0012 (10)
C28	0.0117 (12)	0.0190 (13)	0.0244 (14)	0.0003 (9)	−0.0038 (10)	−0.0044 (10)
C2	0.0293 (14)	0.0189 (13)	0.0280 (15)	−0.0028 (11)	−0.0106 (12)	−0.0011 (10)
C3	0.0413 (17)	0.0211 (13)	0.0215 (14)	0.0039 (11)	−0.0141 (12)	−0.0028 (10)
C4	0.0343 (16)	0.0372 (15)	0.0156 (13)	0.0053 (12)	−0.0030 (11)	−0.0049 (11)
C5	0.0229 (13)	0.0287 (14)	0.0232 (14)	0.0006 (11)	−0.0019 (11)	−0.0006 (11)
C6	0.0239 (13)	0.0108 (12)	0.0191 (13)	0.0007 (9)	−0.0040 (10)	0.0009 (9)
C7	0.0176 (12)	0.0160 (12)	0.0203 (13)	−0.0027 (9)	−0.0045 (10)	0.0004 (10)
C8	0.0161 (12)	0.0172 (12)	0.0171 (13)	−0.0021 (9)	−0.0046 (10)	−0.0015 (9)
C9	0.0203 (12)	0.0144 (12)	0.0165 (12)	−0.0005 (9)	−0.0043 (10)	−0.0063 (9)
C10	0.0193 (13)	0.0210 (14)	0.0302 (14)	−0.0032 (10)	−0.0050 (11)	−0.0019 (11)
C11	0.0248 (14)	0.0226 (14)	0.0351 (16)	0.0024 (11)	−0.0132 (12)	0.0013 (11)

Geometric parameters (Å, º) top

Cl33—C27	1.736 (2)	C19—C20	1.378 (4)
Cl34—C20	1.738 (3)	C20—C21	1.390 (4)
O29—C28	1.349 (3)	C22—C23	1.465 (3)
O30—C21	1.341 (3)	C23—C28	1.399 (3)
N31—C22	1.280 (3)	C23—C24	1.405 (3)
N31—C7	1.479 (3)	C24—C25	1.378 (4)
N32—C15	1.273 (3)	C25—C26	1.388 (4)
N32—C8	1.463 (3)	C26—C27	1.386 (4)
C1—C2	1.385 (4)	C27—C28	1.396 (4)
C1—C6	1.394 (4)	C2—C3	1.382 (4)
C12—C11	1.379 (4)	C3—C4	1.381 (4)
C12—C13	1.385 (4)	C4—C5	1.383 (4)
C13—C14	1.388 (4)	C5—C6	1.385 (4)
C14—C9	1.390 (3)	C6—C7	1.513 (3)
C15—C16	1.457 (3)	C7—C8	1.545 (3)
C16—C17	1.397 (4)	C8—C9	1.519 (3)
C16—C21	1.409 (4)	C9—C10	1.381 (3)
C17—C18	1.376 (4)	C10—C11	1.394 (4)
C18—C19	1.382 (4)

C22—N31—C7	121.14 (19)	C27—C26—C25	119.8 (2)
C15—N32—C8	118.73 (19)	C26—C27—C28	121.4 (2)
C2—C1—C6	121.0 (2)	C26—C27—Cl33	119.82 (19)
C11—C12—C13	119.5 (2)	C28—C27—Cl33	118.69 (18)
C12—C13—C14	120.3 (2)	O29—C28—C27	119.4 (2)
C13—C14—C9	120.5 (2)	O29—C28—C23	122.2 (2)
N32—C15—C16	122.6 (2)	C27—C28—C23	118.4 (2)
C17—C16—C21	119.7 (2)	C3—C2—C1	119.9 (2)
C17—C16—C15	120.3 (2)	C4—C3—C2	119.5 (2)
C21—C16—C15	120.1 (2)	C3—C4—C5	120.6 (2)
C18—C17—C16	120.8 (2)	C4—C5—C6	120.7 (2)
C17—C18—C19	119.7 (2)	C5—C6—C1	118.3 (2)
C20—C19—C18	120.1 (2)	C5—C6—C7	119.7 (2)
C19—C20—C21	121.6 (2)	C1—C6—C7	122.0 (2)
C19—C20—Cl34	120.1 (2)	N31—C7—C6	115.14 (18)
C21—C20—Cl34	118.4 (2)	N31—C7—C8	107.84 (18)
O30—C21—C20	119.6 (2)	C6—C7—C8	112.28 (19)
O30—C21—C16	122.2 (2)	N32—C8—C9	109.64 (17)
C20—C21—C16	118.1 (2)	N32—C8—C7	109.18 (18)
N31—C22—C23	120.2 (2)	C9—C8—C7	110.89 (18)
C28—C23—C24	119.8 (2)	C10—C9—C14	118.8 (2)
C28—C23—C22	120.7 (2)	C10—C9—C8	120.6 (2)
C24—C23—C22	119.6 (2)	C14—C9—C8	120.6 (2)
C25—C24—C23	120.8 (2)	C9—C10—C11	120.9 (2)
C24—C25—C26	119.8 (2)	C12—C11—C10	120.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O29—H29···N31	0.84	1.82	2.564 (3)	147
O30—H30···N32	0.84	1.85	2.597 (3)	147

Funding information

The following funding is acknowledged: Grant-in-Aid for Scientific Research (B) KAKENHI (grant No. 24K00912).

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