(2E,2′E)-1,1′-([1,1′-Biphen­yl]-4,4′-di­yl)bis­[3-(di­meth­yl­amino)­prop-2-en-1-one]

Minagawa, T.; Sadakiyo, M.

doi:10.1107/S2414314624003584

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 9| Part 4| April 2024| x240358

https://doi.org/10.1107/S2414314624003584

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(2E,2′E)-1,1′-([1,1′-Biphenyl]-4,4′-diyl)bis[3-(dimethylamino)prop-2-en-1-one]

Tomohiro Minagawa ^a and Masaaki Sadakiyo ^a ^*

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

Edited by I. Brito, University of Antofagasta, Chile (Received 1 April 2024; accepted 19 April 2024; online 26 April 2024)

The title compound, C₂₂H₂₄N₂O₂, crystallizes in space group P2₁/n. The molecular structure is almost planar except for a tilt of the phenyl rings. The allyl groups on both ends exhibit the trans-form and the connected N atoms show sp² character. The molecules are stacked and assembled along the c-axis direction by C—H⋯π interactions.

Keywords: crystal structure; β-ketoamine; π-conjugated molecule.

CCDC reference: 2349722

Structure description

β-Ketoamines are important not only for various chemical reactions, but also for creating functional complexes (Pettinari et al., 2014 ). Recently, they have also been used as reagents for covalent organic frameworks (Zhao et al., 2023 ). In this work, the crystal structure of the title β-ketoamine was determined. The molecule is almost flat, but the phenyl rings are tilted [dihedral angle = 30.14 (8)°] (Fig. 1) as a result of the repulsion between H atoms on the phenyl rings and intermolecular interactions, i.e., C—H⋯π, with neighboring molecules (Table 1). In addition to the carbonyl and the allyl groups, the amino groups also show a planar character, indicating the sp² character of the N atoms and the π-conjugated character of these functional groups. The bond-angle sums for both N atoms are 360.0°.

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1/C9/C17/C4/C18/C15 and C3/C14/C11/C7/C6/C16 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21—H21B⋯O2ⁱ	0.98	2.51	3.410 (2)	152
C22—H22⋯O1ⁱⁱ	0.98	2.48	3.387 (2)	154
C21—H21⋯Cg2ⁱⁱⁱ	0.98	2.60	3.538 (2)	160
C22—H22B⋯Cg1^iv	0.98	2.70	3.608 (2)	154
Symmetry codes: (i) ; (ii) ; (iii) ; (iv) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Figure 1
Illustration of the title molecule, composed of crystallographically independent atoms with displacement ellipsoids drawn at the 50% probability level.

In the crystal, the molecules are assembled to form a two-dimensional layer-like structure in the (105) plane (Fig. 2). The molecules are stacked perpendicular to this plane through C—H⋯π interactions. Each molecule interacts with three neighboring molecules. Two different phenyl groups on the molecule accept the C donors (C21 and C22), resulting in additional C—H⋯π interactions (Tsuzuki et al., 2000 ) with molecules above and below (Fig. 3). The C21 methyl group on one side interacts with the phenyl ring of the stacked molecule above through a C21—H21⋯Cg2 interaction [C21⋯Cg2 = 3.538 (2) Å], while the C22 methyl group on the other side similarly interacts with the molecule below [C22⋯Cg1 = 3.608 (2) Å] where Cg1 and Cg2 are the centroids of the C1/C9/C17/C4/C18/C15 and C3/C14/C11/C7/C6/C16 rings, respectively. The distances between the phenyl groups are not remarkably short with centroid–centroid separations of 4.363 (1) and 4.833 (1) Å, and no obvious π–π interactions occur with neighboring molecules, indicating that the molecules are assembled mainly through C—H⋯π interactions. C—H⋯O interactions involving H22 and H22B (Table 1) also occur, which also contribute to assemble the molecules.

Figure 2
Packing structure of the title compound along the b axis.

Figure 3
C—H⋯π interactions between neighboring molecules. Symmetry codes: (i) $[{1\over 2}]$ − x, $[{1\over 2}]$ + y, $[{3\over 2}]$ − z; (ii) −x, −y, 2 − z.

Synthesis and crystallization

A mixture of 4,4′-diacetyl biphenyl (0.953 g, 4.00 mmol), anhydrous DMF (12 ml), and N,N-dimethylformamide diethyl acetal (12 ml) was stirred and heated at 90°C under a nitrogen atmosphere for 12 h. After cooling, diethyl ether (20 ml) was added slowly to the reaction mixture, resulting in a yellow powder. The precipitate was collected by suction filtration and it was then immersed in n-pentane for 4 h at room temperature. After that, the precipitate was collected by suction filtration and dried under vacuum at 170°C overnight (0.961 g, 1.98 mmol, yield 50%). Crystals of the title compound were obtained by recrystallization through slow evaporation of a methanol solution. After several days, yellow crystals were obtained.

Refinement

Details of crystal data, data collections, and structure refinements are shown in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₂H₂₄N₂O₂
M_r	348.43
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	90
a, b, c (Å)	15.862 (1), 6.0503 (4), 19.0640 (12)
β (°)	105.287 (3)
V (Å³)	1764.8 (2)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.08
Crystal size (mm)	0.40 × 0.20 × 0.20

Data collection
Diffractometer	Bruker PHOTON II CPAD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.669, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	21542, 4738, 3539
R_int	0.076
(sin θ/λ)_max (Å⁻¹)	0.731

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.154, 1.08
No. of reflections	4738
No. of parameters	239
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.25
Computer programs: APEX4 and SAINT (Bruker, 2021 ), SIR2019 (Burla et al., 2015 ), SHELXL2018/3 (Sheldrick, 2015 ), DIAMOND (Brandenburg, 2014 ) and Yadokari-XG (Kabuto et al., 2009 ).

Structural data

CCDC reference: 2349722

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314624003584/bx4027sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314624003584/bx4027Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314624003584/bx4027Isup3.cdx

Supporting information file. DOI: https://doi.org/10.1107/S2414314624003584/bx4027Isup4.cml

checkCIF report

Computing details top

(2E,2'E)-1,1'-([1,1'-Biphenyl]-4,4'-diyl)bis[3-(dimethylamino)prop-2-en-1-one] top

Crystal data top

C₂₂H₂₄N₂O₂	F(000) = 744
M_r = 348.43	D_x = 1.311 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71069 Å
a = 15.862 (1) Å	Cell parameters from 2411 reflections
b = 6.0503 (4) Å	θ = 3.0–29.0°
c = 19.0640 (12) Å	µ = 0.08 mm⁻¹
β = 105.287 (3)°	T = 90 K
V = 1764.8 (2) Å³	Block, yellow
Z = 4	0.40 × 0.20 × 0.20 mm

Data collection top

Bruker PHOTON II CPAD diffractometer	3539 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.076
φ and ω scans	θ_max = 31.3°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −22→23
T_min = 0.669, T_max = 0.746	k = −8→8
21542 measured reflections	l = −27→26
4738 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.063	H-atom parameters constrained
wR(F²) = 0.154	w = 1/[σ²(F_o²) + (0.0561P)² + 0.8647P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
4738 reflections	Δρ_max = 0.31 e Å⁻³
239 parameters	Δρ_min = −0.25 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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

All hydrogen atoms were fixed geometrically and refined using a riding-model approximation with C—H = 0.95 (for phenyl and allyl) and 0.98 (for methyl) Å.

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

	x	y	z	U_iso*/U_eq
O1	0.44366 (8)	0.0656 (2)	0.82473 (8)	0.0251 (3)
O2	−0.18571 (8)	−0.6345 (2)	0.92406 (8)	0.0260 (3)
C1	0.08648 (11)	−0.3027 (3)	0.88219 (9)	0.0172 (3)
C2	0.42078 (11)	−0.1318 (3)	0.82155 (9)	0.0183 (4)
N1	−0.35165 (9)	−0.1752 (2)	0.97342 (8)	0.0206 (3)
N2	0.60934 (9)	−0.3981 (3)	0.77673 (9)	0.0216 (3)
C3	0.33358 (11)	−0.1860 (3)	0.83472 (9)	0.0164 (3)
C4	−0.07530 (11)	−0.3830 (3)	0.91419 (9)	0.0182 (4)
C5	−0.16200 (11)	−0.4379 (3)	0.92887 (10)	0.0194 (4)
C6	0.23300 (11)	−0.4325 (3)	0.87142 (9)	0.0184 (4)
H6	0.220473	−0.575129	0.886905	0.022*
C7	0.17109 (11)	−0.2637 (3)	0.86495 (9)	0.0171 (4)
C8	0.47315 (11)	−0.3113 (3)	0.80669 (10)	0.0190 (4)
H8	0.454442	−0.460179	0.807627	0.023*
C9	0.04331 (11)	−0.1358 (3)	0.90959 (10)	0.0194 (4)
H9	0.069054	0.006774	0.918150	0.023*
C10	−0.29110 (11)	−0.3106 (3)	0.96087 (9)	0.0197 (4)
H10	−0.302961	−0.463891	0.963229	0.024*
C11	0.19194 (11)	−0.0561 (3)	0.84176 (10)	0.0188 (4)
H11	0.150491	0.060452	0.835705	0.023*
C12	−0.21424 (11)	−0.2595 (3)	0.94506 (10)	0.0204 (4)
H12	−0.195669	−0.110271	0.944727	0.024*
C13	0.55029 (11)	−0.2624 (3)	0.79123 (10)	0.0197 (4)
H13	0.563685	−0.109429	0.790785	0.024*
C14	0.27188 (11)	−0.0173 (3)	0.82748 (9)	0.0182 (4)
H14	0.284837	0.125692	0.812585	0.022*
C15	0.04694 (11)	−0.5114 (3)	0.87134 (10)	0.0206 (4)
H15	0.074488	−0.627754	0.852269	0.025*
C16	0.31225 (11)	−0.3953 (3)	0.85566 (9)	0.0176 (4)
H16	0.352524	−0.513573	0.859146	0.021*
C17	−0.03656 (11)	−0.1741 (3)	0.92460 (10)	0.0197 (4)
H17	−0.065153	−0.056678	0.942160	0.024*
C18	−0.03162 (11)	−0.5510 (3)	0.88793 (10)	0.0193 (4)
H18	−0.056200	−0.695105	0.881307	0.023*
C19	−0.42660 (11)	−0.2587 (3)	0.99574 (10)	0.0231 (4)
H19	−0.425634	−0.420614	0.995747	0.035*
H19A	−0.480571	−0.206431	0.961739	0.035*
H19B	−0.424069	−0.205172	1.044775	0.035*
C20	0.68514 (12)	−0.3137 (3)	0.75587 (11)	0.0259 (4)
H20	0.683659	−0.151744	0.755483	0.039*
H20A	0.684187	−0.367920	0.707229	0.039*
H20B	0.738614	−0.364478	0.790844	0.039*
C21	−0.34611 (12)	0.0646 (3)	0.96831 (11)	0.0248 (4)
H21	−0.334516	0.129235	1.017057	0.037*
H21A	−0.401469	0.122254	0.937915	0.037*
H21B	−0.298604	0.103377	0.946522	0.037*
C22	0.60316 (12)	−0.6375 (3)	0.78032 (11)	0.0239 (4)
H22	0.553718	−0.677418	0.799595	0.036*
H22A	0.657287	−0.696557	0.812301	0.036*
H22B	0.594317	−0.699911	0.731468	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0229 (6)	0.0164 (6)	0.0391 (8)	−0.0025 (5)	0.0138 (6)	−0.0007 (6)
O2	0.0243 (7)	0.0191 (7)	0.0391 (8)	−0.0041 (5)	0.0161 (6)	−0.0028 (6)
C1	0.0160 (8)	0.0166 (8)	0.0198 (8)	0.0012 (7)	0.0060 (7)	0.0014 (7)
C2	0.0168 (8)	0.0191 (9)	0.0206 (8)	−0.0004 (7)	0.0076 (7)	−0.0003 (7)
N1	0.0188 (7)	0.0179 (8)	0.0273 (8)	−0.0018 (6)	0.0098 (6)	−0.0017 (6)
N2	0.0194 (7)	0.0180 (8)	0.0314 (8)	−0.0005 (6)	0.0135 (7)	0.0007 (6)
C3	0.0169 (8)	0.0160 (8)	0.0171 (8)	−0.0007 (7)	0.0057 (7)	−0.0006 (7)
C4	0.0178 (8)	0.0183 (9)	0.0201 (8)	0.0005 (7)	0.0075 (7)	0.0015 (7)
C5	0.0203 (8)	0.0194 (9)	0.0201 (8)	−0.0007 (7)	0.0083 (7)	0.0004 (7)
C6	0.0189 (8)	0.0141 (8)	0.0240 (9)	0.0003 (7)	0.0089 (7)	0.0005 (7)
C7	0.0186 (8)	0.0147 (8)	0.0194 (8)	−0.0002 (7)	0.0073 (7)	−0.0010 (7)
C8	0.0170 (8)	0.0187 (9)	0.0237 (9)	−0.0014 (7)	0.0094 (7)	−0.0001 (7)
C9	0.0205 (8)	0.0141 (8)	0.0251 (9)	−0.0024 (7)	0.0085 (7)	−0.0018 (7)
C10	0.0207 (8)	0.0176 (9)	0.0216 (9)	−0.0004 (7)	0.0068 (7)	−0.0006 (7)
C11	0.0166 (8)	0.0151 (8)	0.0250 (9)	0.0023 (7)	0.0056 (7)	−0.0012 (7)
C12	0.0210 (8)	0.0171 (9)	0.0257 (9)	−0.0017 (7)	0.0109 (7)	−0.0003 (7)
C13	0.0204 (8)	0.0158 (8)	0.0246 (9)	−0.0007 (7)	0.0087 (7)	0.0000 (7)
C14	0.0198 (8)	0.0145 (8)	0.0212 (8)	−0.0002 (7)	0.0071 (7)	0.0010 (7)
C15	0.0209 (8)	0.0151 (8)	0.0284 (9)	0.0016 (7)	0.0110 (8)	−0.0020 (7)
C16	0.0171 (8)	0.0155 (8)	0.0210 (8)	0.0022 (7)	0.0065 (7)	0.0003 (7)
C17	0.0208 (8)	0.0166 (9)	0.0248 (9)	−0.0003 (7)	0.0117 (7)	−0.0043 (7)
C18	0.0180 (8)	0.0143 (8)	0.0259 (9)	−0.0016 (7)	0.0064 (7)	0.0004 (7)
C19	0.0194 (8)	0.0239 (10)	0.0292 (10)	−0.0010 (7)	0.0120 (8)	0.0022 (8)
C20	0.0203 (9)	0.0246 (10)	0.0375 (11)	−0.0010 (8)	0.0160 (8)	0.0029 (8)
C21	0.0267 (9)	0.0192 (9)	0.0315 (10)	0.0013 (8)	0.0132 (8)	0.0011 (8)
C22	0.0237 (9)	0.0188 (9)	0.0324 (10)	0.0022 (7)	0.0132 (8)	0.0009 (8)

Geometric parameters (Å, º) top

O1—C2	1.245 (2)	C9—H9	0.9500
O2—C5	1.243 (2)	C10—C12	1.366 (2)
C1—C9	1.396 (2)	C10—H10	0.9500
C1—C15	1.401 (2)	C11—C14	1.385 (2)
C1—C7	1.482 (2)	C11—H11	0.9500
C2—C8	1.440 (2)	C12—H12	0.9500
C2—C3	1.506 (2)	C13—H13	0.9500
N1—C10	1.331 (2)	C14—H14	0.9500
N1—C19	1.455 (2)	C15—C18	1.385 (2)
N1—C21	1.458 (2)	C15—H15	0.9500
N2—C13	1.329 (2)	C16—H16	0.9500
N2—C22	1.455 (2)	C17—H17	0.9500
N2—C20	1.455 (2)	C18—H18	0.9500
C3—C14	1.395 (2)	C19—H19	0.9800
C3—C16	1.396 (2)	C19—H19A	0.9800
C4—C18	1.395 (2)	C19—H19B	0.9800
C4—C17	1.397 (2)	C20—H20	0.9800
C4—C5	1.511 (2)	C20—H20A	0.9800
C5—C12	1.443 (2)	C20—H20B	0.9800
C6—C16	1.386 (2)	C21—H21	0.9800
C6—C7	1.399 (2)	C21—H21A	0.9800
C6—H6	0.9500	C21—H21B	0.9800
C7—C11	1.400 (2)	C22—H22	0.9800
C8—C13	1.364 (2)	C22—H22A	0.9800
C8—H8	0.9500	C22—H22B	0.9800
C9—C17	1.390 (2)

C9—C1—C15	117.55 (15)	N2—C13—C8	129.23 (17)
C9—C1—C7	122.00 (16)	N2—C13—H13	115.4
C15—C1—C7	120.45 (15)	C8—C13—H13	115.4
O1—C2—C8	123.86 (15)	C11—C14—C3	120.76 (16)
O1—C2—C3	118.00 (15)	C11—C14—H14	119.6
C8—C2—C3	118.14 (15)	C3—C14—H14	119.6
C10—N1—C19	121.53 (15)	C18—C15—C1	121.12 (16)
C10—N1—C21	122.76 (15)	C18—C15—H15	119.4
C19—N1—C21	115.68 (14)	C1—C15—H15	119.4
C13—N2—C22	123.09 (15)	C6—C16—C3	120.76 (16)
C13—N2—C20	121.23 (15)	C6—C16—H16	119.6
C22—N2—C20	115.68 (15)	C3—C16—H16	119.6
C14—C3—C16	118.36 (15)	C9—C17—C4	120.82 (16)
C14—C3—C2	118.40 (15)	C9—C17—H17	119.6
C16—C3—C2	123.21 (15)	C4—C17—H17	119.6
C18—C4—C17	117.95 (15)	C15—C18—C4	121.20 (16)
C18—C4—C5	117.96 (16)	C15—C18—H18	119.4
C17—C4—C5	124.09 (15)	C4—C18—H18	119.4
O2—C5—C12	123.49 (16)	N1—C19—H19	109.5
O2—C5—C4	117.97 (16)	N1—C19—H19A	109.5
C12—C5—C4	118.50 (15)	H19—C19—H19A	109.5
C16—C6—C7	121.20 (16)	N1—C19—H19B	109.5
C16—C6—H6	119.4	H19—C19—H19B	109.5
C7—C6—H6	119.4	H19A—C19—H19B	109.5
C6—C7—C11	117.64 (15)	N2—C20—H20	109.5
C6—C7—C1	121.32 (15)	N2—C20—H20A	109.5
C11—C7—C1	121.04 (15)	H20—C20—H20A	109.5
C13—C8—C2	118.39 (16)	N2—C20—H20B	109.5
C13—C8—H8	120.8	H20—C20—H20B	109.5
C2—C8—H8	120.8	H20A—C20—H20B	109.5
C17—C9—C1	121.34 (16)	N1—C21—H21	109.5
C17—C9—H9	119.3	N1—C21—H21A	109.5
C1—C9—H9	119.3	H21—C21—H21A	109.5
N1—C10—C12	128.94 (17)	N1—C21—H21B	109.5
N1—C10—H10	115.5	H21—C21—H21B	109.5
C12—C10—H10	115.5	H21A—C21—H21B	109.5
C14—C11—C7	121.23 (16)	N2—C22—H22	109.5
C14—C11—H11	119.4	N2—C22—H22A	109.5
C7—C11—H11	119.4	H22—C22—H22A	109.5
C10—C12—C5	118.29 (16)	N2—C22—H22B	109.5
C10—C12—H12	120.9	H22—C22—H22B	109.5
C5—C12—H12	120.9	H22A—C22—H22B	109.5

O1—C2—C3—C14	19.5 (2)	C1—C7—C11—C14	178.24 (16)
C8—C2—C3—C14	−161.06 (16)	N1—C10—C12—C5	−175.95 (17)
O1—C2—C3—C16	−158.78 (17)	O2—C5—C12—C10	4.7 (3)
C8—C2—C3—C16	20.7 (3)	C4—C5—C12—C10	−177.69 (16)
C18—C4—C5—O2	7.3 (2)	C22—N2—C13—C8	−4.7 (3)
C17—C4—C5—O2	−173.35 (18)	C20—N2—C13—C8	175.17 (19)
C18—C4—C5—C12	−170.47 (16)	C2—C8—C13—N2	179.18 (18)
C17—C4—C5—C12	8.9 (3)	C7—C11—C14—C3	1.0 (3)
C16—C6—C7—C11	0.2 (3)	C16—C3—C14—C11	0.9 (3)
C16—C6—C7—C1	−179.64 (16)	C2—C3—C14—C11	−177.45 (16)
C9—C1—C7—C6	149.01 (17)	C9—C1—C15—C18	−0.7 (3)
C15—C1—C7—C6	−30.9 (3)	C7—C1—C15—C18	179.29 (16)
C9—C1—C7—C11	−30.8 (3)	C7—C6—C16—C3	1.8 (3)
C15—C1—C7—C11	149.25 (18)	C14—C3—C16—C6	−2.3 (3)
O1—C2—C8—C13	−3.7 (3)	C2—C3—C16—C6	175.97 (16)
C3—C2—C8—C13	176.87 (16)	C1—C9—C17—C4	1.4 (3)
C15—C1—C9—C17	−0.9 (3)	C18—C4—C17—C9	−0.4 (3)
C7—C1—C9—C17	179.15 (16)	C5—C4—C17—C9	−179.73 (16)
C19—N1—C10—C12	−174.60 (18)	C1—C15—C18—C4	1.7 (3)
C21—N1—C10—C12	3.2 (3)	C17—C4—C18—C15	−1.2 (3)
C6—C7—C11—C14	−1.6 (3)	C5—C4—C18—C15	178.21 (16)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1/C9/C17/C4/C18/C15 and C3/C14/C11/C7/C6/C16 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21B···O2ⁱ	0.98	2.51	3.410 (2)	152
C22—H22···O1ⁱⁱ	0.98	2.48	3.387 (2)	154
C21—H21···Cg2ⁱⁱⁱ	0.98	2.60	3.538 (2)	160
C22—H22B···Cg1^iv	0.98	2.70	3.608 (2)	154

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

Funding information

Funding for this research was provided by: Japan Society for the Promotion of Science (grant No. 21K05089).

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