(E)-1-(3,4-Di­meth­oxy­phen­yl)-3-(1,3-diphenyl-1H-pyrazol-4-yl)prop-2-en-1-one

Sung, J.

doi:10.1107/S2414314624008666

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 9| Part 9| September 2024| x240866

https://doi.org/10.1107/S2414314624008666

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(E)-1-(3,4-Dimethoxyphenyl)-3-(1,3-diphenyl-1H-pyrazol-4-yl)prop-2-en-1-one

Jiha Sung ^a ^*

^aDepartment of Applied Chemistry, Dongduk Women's University, Seoul 136-714, Republic of Korea
^*Correspondence e-mail: dddklab@gmail.com

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 28 August 2024; accepted 3 September 2024; online 6 September 2024)

In the title compound, C₂₆H₂₂N₂O₃, the dihedral angle between the benzene and pyrazole rings of the chalcone unit is 88.3 (1)°. The pyrazole ring has two attached phenyl rings that form dihedral angles with the pyrazole ring of 22.6 (2) and 40.0 (1)°. In the crystal, pairwise C—H⋯O hydrogen bonds generate R²₂(20) inversion dimers.

Keywords: crystal structure; pyrazole; chalcone; C—H⋯O hydrogen bonds.

CCDC reference: 2381555

Structure description

Pyrazoles are promising scaffolds in medicinal chemistry due to their versatile biological efficacy, including antibacterial, anti-inflammatory, antioxidant, antidepressant, and anticancer activity (Brullo et al., 2020 ; Ebenezer et al., 2022 ). As a result of intensive research on the anticancer activity of pyrazole-containing molecules, a number of anticancer drugs such as niraparib, critinib and darolutamide have been developed and are commercially available (Sivaramakarthikeyan et al., 2020 ). Chalcones also exhibit various physiological phenomena, including anticancer activity (Elkanzi et al., 2022 ). As part of our ongoing research to develop new chalcones derivatives (Sung, 2019 ) with anti-cancer activities, the pyrazole-containing chalcone title compound was synthesized and its crystal structure was determined.

The title compound, C₂₆H₂₂N₂O₃, was prepared by a Claisen–Schmidt condensation reaction between 3,4-dimehoxyaceophenone and 1,3-diphenyl-1H-pyrazole-4-carbaldehyde (Fig. 1). The molecular structure of title compound is shown in Fig. 2. The C=C and C=O double bonds usually lie in the same plane in the enone bridge of the chalcone unit. However, in this molecule, the O1—C1—C8—C9 torsion angle is 17.3 (2)°, indicating a significant twist. The C2–C7 benzene ring has two methoxy groups attached at C4 and C5, which are twisted from the ring plane with torsion angles of 6.1 (2)° [C3—C4—O2—C10] and −7.3 (2)° [C6—C5—O3—C11]. The pyrazole ring (N1/N2/C14/C12/C13) has the C15–C20 and C21–C26 phenyl groups attached to atoms N1 and C14, respectively. The C15–C20 and C21–C26 phenyl rings make dihedral angles with the pyrazole ring of 22.6 (2) and 40.0 (1)°, respectively, while the dihedral angle between the phenyl rings is 53.3 (3)°. In the crystal, pairs of C—H—O hydrogen bonds generate inversion dimers with graph-set notation R₂² (20) (Table 1, Fig. 3).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O2ⁱ	0.94	2.34	3.2648 (19)	169
Symmetry code: (i) .

Figure 1
Synthetic scheme for the title compound.

Figure 2
The molecular structure of the title compound, showing displacement ellipsoids drawn at the 50% probability level.

Figure 3
Part of the crystal structure of the title compound, showing the weak C—H⋯O pairwise hydrogen bonds that form R₂²(20) dimers.

Synthesis and crystallization

3,4-Dimethoxyaceophenone (180 mg, 1 mmol) was dissolved in 20 ml of ethanol. Then, 1,3-diphenyl-1H-pyrazole-4-carbaldehyde (248 mg, 1 mmol) was slowly added until a clear solution was formed. The temperature of reaction mixture was adjusted to 276–277 K using an ice bath. To the cooled reaction mixture was added 1.5 ml of 30% aqueous KOH solution, and the reaction mixture was stirred at room temperature for 30 h. This mixture was poured into iced water (50 ml) and was acidified (pH = 3) with 3 N HCl solution to give a precipitate. After filtration, the crude solid was recrystallized from ethanol solution to form crystals in the form of yellow blocks suitable for X-ray diffraction.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₆H₂₂N₂O₃
M_r	410.45
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	223
a, b, c (Å)	9.342 (3), 10.524 (3), 11.967 (4)
α, β, γ (°)	73.831 (10), 79.643 (11), 72.648 (10)
V (Å³)	1072.6 (6)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.08
Crystal size (mm)	0.26 × 0.22 × 0.07

Data collection
Diffractometer	PHOTON III M14
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.706, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	39655, 5269, 4173
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.115, 1.04
No. of reflections	5269
No. of parameters	282
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.20
Computer programs: APEX2 and SAINT (Bruker, 2012 ), SHELXS (Sheldrick, 2008 ), SHELXL2014/7 (Sheldrick, 2015 ), SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 2381555

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314624008666/hb4483sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314624008666/hb4483Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314624008666/hb4483Isup3.cml

checkCIF report

Computing details top

(E)-1-(3,4-Dimethoxyphenyl)-3-(1,3-diphenyl-1H-pyrazol-4-yl)prop-2-en-1-one top

Crystal data top

C₂₆H₂₂N₂O₃	Z = 2
M_r = 410.45	F(000) = 432
Triclinic, P1	D_x = 1.271 Mg m⁻³
a = 9.342 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.524 (3) Å	Cell parameters from 9940 reflections
c = 11.967 (4) Å	θ = 2.3–28.2°
α = 73.831 (10)°	µ = 0.08 mm⁻¹
β = 79.643 (11)°	T = 223 K
γ = 72.648 (10)°	BLOCK, yellow
V = 1072.6 (6) Å³	0.26 × 0.22 × 0.07 mm

Data collection top

PHOTON III M14 diffractometer	4173 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.044
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θ_max = 28.3°, θ_min = 2.1°
T_min = 0.706, T_max = 0.746	h = −12→12
39655 measured reflections	k = −13→13
5269 independent reflections	l = −15→15

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.115	w = 1/[σ²(F_o²) + (0.0449P)² + 0.3885P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
5269 reflections	Δρ_max = 0.24 e Å⁻³
282 parameters	Δρ_min = −0.20 e Å⁻³
0 restraints

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
C1	0.62809 (17)	0.71283 (14)	0.49957 (12)	0.0323 (3)
C2	0.67643 (16)	0.84296 (13)	0.47121 (12)	0.0289 (3)
C3	0.70448 (15)	0.90841 (13)	0.35225 (11)	0.0278 (3)
H3	0.6908	0.8711	0.2934	0.033*
C4	0.75205 (14)	1.02730 (13)	0.32222 (11)	0.0256 (3)
C5	0.77516 (16)	1.08293 (13)	0.41023 (12)	0.0289 (3)
C6	0.74834 (19)	1.01806 (16)	0.52704 (13)	0.0380 (3)
H6	0.7640	1.0540	0.5861	0.046*
C7	0.69805 (18)	0.89929 (15)	0.55667 (12)	0.0367 (3)
H7	0.6785	0.8568	0.6360	0.044*
C8	0.55681 (16)	0.66700 (14)	0.61955 (12)	0.0305 (3)
H8	0.5185	0.7306	0.6663	0.037*
C9	0.54487 (16)	0.53814 (14)	0.66390 (12)	0.0299 (3)
H9	0.5866	0.4748	0.6172	0.036*
C10	0.7475 (2)	1.05899 (18)	0.11652 (13)	0.0506 (5)
H10A	0.8065	0.9658	0.1172	0.076*
H10B	0.7719	1.1196	0.0427	0.076*
H10C	0.6410	1.0632	0.1260	0.076*
C11	0.8254 (2)	1.27120 (18)	0.45672 (15)	0.0502 (4)
H11A	0.7316	1.2800	0.5078	0.075*
H11B	0.8386	1.3616	0.4178	0.075*
H11C	0.9089	1.2194	0.5026	0.075*
C12	0.47133 (15)	0.49005 (13)	0.77989 (12)	0.0276 (3)
C13	0.35511 (16)	0.56706 (13)	0.84202 (12)	0.0301 (3)
H13	0.3103	0.6616	0.8181	0.036*
C14	0.49721 (15)	0.35452 (13)	0.85328 (11)	0.0254 (3)
C15	0.19811 (15)	0.51457 (13)	1.03298 (12)	0.0274 (3)
C16	0.07757 (16)	0.62931 (14)	1.00652 (13)	0.0336 (3)
H16	0.0756	0.6874	0.9309	0.040*
C17	−0.04030 (17)	0.65744 (16)	1.09308 (15)	0.0397 (4)
H17	−0.1219	0.7351	1.0755	0.048*
C18	−0.03903 (19)	0.57258 (17)	1.20473 (15)	0.0439 (4)
H18	−0.1196	0.5915	1.2625	0.053*
C19	0.08327 (19)	0.45892 (18)	1.23016 (14)	0.0440 (4)
H19	0.0855	0.4014	1.3060	0.053*
C20	0.20220 (17)	0.42922 (15)	1.14506 (13)	0.0356 (3)
H20	0.2845	0.3523	1.1631	0.043*
C21	0.61238 (15)	0.22895 (13)	0.83440 (11)	0.0257 (3)
C22	0.75946 (16)	0.23372 (14)	0.78641 (12)	0.0324 (3)
H22	0.7839	0.3184	0.7613	0.039*
C23	0.86940 (17)	0.11392 (16)	0.77567 (14)	0.0389 (3)
H23	0.9679	0.1181	0.7436	0.047*
C24	0.83513 (18)	−0.01186 (15)	0.81191 (13)	0.0395 (4)
H24	0.9101	−0.0925	0.8046	0.047*
C25	0.68948 (18)	−0.01789 (14)	0.85903 (13)	0.0371 (3)
H25	0.6657	−0.1028	0.8837	0.045*
C26	0.57853 (16)	0.10188 (13)	0.86983 (12)	0.0310 (3)
H26	0.4800	0.0972	0.9012	0.037*
N1	0.31718 (13)	0.48180 (11)	0.94375 (10)	0.0276 (2)
N2	0.40423 (12)	0.34957 (11)	0.95287 (10)	0.0271 (2)
O1	0.64801 (16)	0.64685 (12)	0.42551 (10)	0.0540 (3)
O2	0.78144 (12)	1.10062 (9)	0.21009 (8)	0.0311 (2)
O3	0.82098 (12)	1.20091 (10)	0.37080 (9)	0.0362 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0405 (8)	0.0263 (7)	0.0269 (7)	−0.0117 (6)	0.0029 (6)	−0.0019 (5)
C2	0.0330 (7)	0.0244 (6)	0.0253 (6)	−0.0089 (5)	0.0017 (5)	−0.0012 (5)
C3	0.0329 (7)	0.0256 (6)	0.0234 (6)	−0.0089 (5)	0.0005 (5)	−0.0047 (5)
C4	0.0267 (6)	0.0222 (6)	0.0222 (6)	−0.0045 (5)	0.0012 (5)	−0.0006 (5)
C5	0.0325 (7)	0.0257 (6)	0.0277 (7)	−0.0102 (5)	−0.0007 (5)	−0.0037 (5)
C6	0.0557 (10)	0.0390 (8)	0.0243 (7)	−0.0222 (7)	−0.0021 (6)	−0.0063 (6)
C7	0.0525 (9)	0.0354 (8)	0.0216 (6)	−0.0198 (7)	0.0000 (6)	0.0008 (6)
C8	0.0355 (7)	0.0252 (6)	0.0269 (7)	−0.0091 (5)	0.0039 (6)	−0.0033 (5)
C9	0.0336 (7)	0.0251 (6)	0.0269 (7)	−0.0071 (5)	0.0020 (5)	−0.0035 (5)
C10	0.0866 (14)	0.0502 (10)	0.0237 (7)	−0.0381 (10)	−0.0088 (8)	0.0007 (7)
C11	0.0754 (13)	0.0474 (10)	0.0415 (9)	−0.0368 (9)	0.0012 (8)	−0.0146 (8)
C12	0.0328 (7)	0.0203 (6)	0.0266 (6)	−0.0085 (5)	0.0000 (5)	−0.0014 (5)
C13	0.0361 (7)	0.0208 (6)	0.0289 (7)	−0.0081 (5)	0.0008 (6)	−0.0009 (5)
C14	0.0275 (6)	0.0222 (6)	0.0253 (6)	−0.0090 (5)	−0.0008 (5)	−0.0020 (5)
C15	0.0290 (7)	0.0255 (6)	0.0285 (7)	−0.0102 (5)	0.0020 (5)	−0.0076 (5)
C16	0.0343 (8)	0.0278 (7)	0.0371 (8)	−0.0071 (6)	−0.0020 (6)	−0.0073 (6)
C17	0.0315 (8)	0.0339 (8)	0.0538 (10)	−0.0054 (6)	0.0012 (7)	−0.0180 (7)
C18	0.0381 (8)	0.0480 (9)	0.0481 (9)	−0.0162 (7)	0.0150 (7)	−0.0226 (8)
C19	0.0468 (9)	0.0492 (9)	0.0315 (8)	−0.0161 (8)	0.0083 (7)	−0.0064 (7)
C20	0.0360 (8)	0.0334 (7)	0.0314 (7)	−0.0068 (6)	0.0016 (6)	−0.0040 (6)
C21	0.0298 (7)	0.0237 (6)	0.0208 (6)	−0.0063 (5)	−0.0023 (5)	−0.0020 (5)
C22	0.0322 (7)	0.0310 (7)	0.0313 (7)	−0.0098 (6)	−0.0012 (6)	−0.0030 (6)
C23	0.0297 (7)	0.0439 (9)	0.0357 (8)	−0.0026 (6)	−0.0002 (6)	−0.0075 (7)
C24	0.0425 (9)	0.0327 (8)	0.0347 (8)	0.0061 (6)	−0.0071 (7)	−0.0096 (6)
C25	0.0512 (9)	0.0237 (7)	0.0338 (8)	−0.0071 (6)	−0.0055 (7)	−0.0050 (6)
C26	0.0344 (7)	0.0268 (7)	0.0304 (7)	−0.0100 (6)	−0.0013 (6)	−0.0039 (5)
N1	0.0308 (6)	0.0202 (5)	0.0271 (6)	−0.0055 (4)	0.0004 (5)	−0.0019 (4)
N2	0.0288 (6)	0.0197 (5)	0.0279 (6)	−0.0051 (4)	0.0008 (4)	−0.0020 (4)
O1	0.0929 (10)	0.0427 (6)	0.0342 (6)	−0.0384 (7)	0.0159 (6)	−0.0134 (5)
O2	0.0460 (6)	0.0264 (5)	0.0203 (4)	−0.0153 (4)	−0.0013 (4)	0.0004 (4)
O3	0.0517 (6)	0.0316 (5)	0.0299 (5)	−0.0223 (5)	0.0001 (5)	−0.0050 (4)

Geometric parameters (Å, º) top

C1—O1	1.2283 (18)	C13—N1	1.3560 (17)
C1—C8	1.4832 (19)	C13—H13	0.9400
C1—C2	1.4998 (19)	C14—N2	1.3408 (17)
C2—C7	1.386 (2)	C14—C21	1.4784 (18)
C2—C3	1.4133 (18)	C15—C16	1.390 (2)
C3—C4	1.3842 (18)	C15—C20	1.391 (2)
C3—H3	0.9400	C15—N1	1.4302 (17)
C4—O2	1.3743 (15)	C16—C17	1.393 (2)
C4—C5	1.4139 (19)	C16—H16	0.9400
C5—O3	1.3659 (16)	C17—C18	1.385 (2)
C5—C6	1.3884 (19)	C17—H17	0.9400
C6—C7	1.397 (2)	C18—C19	1.391 (2)
C6—H6	0.9400	C18—H18	0.9400
C7—H7	0.9400	C19—C20	1.390 (2)
C8—C9	1.3422 (18)	C19—H19	0.9400
C8—H8	0.9400	C20—H20	0.9400
C9—C12	1.4588 (19)	C21—C26	1.3988 (18)
C9—H9	0.9400	C21—C22	1.4005 (19)
C10—O2	1.4249 (19)	C22—C23	1.390 (2)
C10—H10A	0.9700	C22—H22	0.9400
C10—H10B	0.9700	C23—C24	1.388 (2)
C10—H10C	0.9700	C23—H23	0.9400
C11—O3	1.4363 (19)	C24—C25	1.389 (2)
C11—H11A	0.9700	C24—H24	0.9400
C11—H11B	0.9700	C25—C26	1.394 (2)
C11—H11C	0.9700	C25—H25	0.9400
C12—C13	1.3817 (19)	C26—H26	0.9400
C12—C14	1.4274 (17)	N1—N2	1.3719 (15)

O1—C1—C8	121.61 (13)	N2—C14—C12	111.62 (11)
O1—C1—C2	120.66 (12)	N2—C14—C21	119.59 (11)
C8—C1—C2	117.73 (12)	C12—C14—C21	128.73 (12)
C7—C2—C3	118.98 (12)	C16—C15—C20	120.49 (13)
C7—C2—C1	122.70 (12)	C16—C15—N1	119.88 (12)
C3—C2—C1	118.31 (12)	C20—C15—N1	119.61 (12)
C4—C3—C2	120.18 (12)	C15—C16—C17	119.35 (14)
C4—C3—H3	119.9	C15—C16—H16	120.3
C2—C3—H3	119.9	C17—C16—H16	120.3
O2—C4—C3	125.50 (12)	C18—C17—C16	120.93 (14)
O2—C4—C5	114.22 (11)	C18—C17—H17	119.5
C3—C4—C5	120.28 (12)	C16—C17—H17	119.5
O3—C5—C6	125.18 (13)	C17—C18—C19	119.00 (14)
O3—C5—C4	115.36 (11)	C17—C18—H18	120.5
C6—C5—C4	119.45 (12)	C19—C18—H18	120.5
C5—C6—C7	119.92 (14)	C20—C19—C18	120.95 (15)
C5—C6—H6	120.0	C20—C19—H19	119.5
C7—C6—H6	120.0	C18—C19—H19	119.5
C2—C7—C6	121.18 (13)	C19—C20—C15	119.26 (14)
C2—C7—H7	119.4	C19—C20—H20	120.4
C6—C7—H7	119.4	C15—C20—H20	120.4
C9—C8—C1	122.51 (13)	C26—C21—C22	118.70 (12)
C9—C8—H8	118.7	C26—C21—C14	120.51 (12)
C1—C8—H8	118.7	C22—C21—C14	120.71 (12)
C8—C9—C12	124.25 (13)	C23—C22—C21	120.31 (13)
C8—C9—H9	117.9	C23—C22—H22	119.8
C12—C9—H9	117.9	C21—C22—H22	119.8
O2—C10—H10A	109.5	C24—C23—C22	120.61 (14)
O2—C10—H10B	109.5	C24—C23—H23	119.7
H10A—C10—H10B	109.5	C22—C23—H23	119.7
O2—C10—H10C	109.5	C23—C24—C25	119.64 (13)
H10A—C10—H10C	109.5	C23—C24—H24	120.2
H10B—C10—H10C	109.5	C25—C24—H24	120.2
O3—C11—H11A	109.5	C24—C25—C26	120.07 (14)
O3—C11—H11B	109.5	C24—C25—H25	120.0
H11A—C11—H11B	109.5	C26—C25—H25	120.0
O3—C11—H11C	109.5	C25—C26—C21	120.66 (14)
H11A—C11—H11C	109.5	C25—C26—H26	119.7
H11B—C11—H11C	109.5	C21—C26—H26	119.7
C13—C12—C14	104.13 (11)	C13—N1—N2	111.93 (11)
C13—C12—C9	126.94 (12)	C13—N1—C15	127.64 (11)
C14—C12—C9	128.89 (12)	N2—N1—C15	120.36 (10)
N1—C13—C12	107.76 (12)	C14—N2—N1	104.55 (10)
N1—C13—H13	126.1	C4—O2—C10	117.79 (11)
C12—C13—H13	126.1	C5—O3—C11	117.12 (11)

O1—C1—C2—C7	−160.59 (16)	C16—C17—C18—C19	0.8 (2)
C8—C1—C2—C7	19.1 (2)	C17—C18—C19—C20	−0.7 (3)
O1—C1—C2—C3	17.8 (2)	C18—C19—C20—C15	−0.1 (2)
C8—C1—C2—C3	−162.53 (13)	C16—C15—C20—C19	0.8 (2)
C7—C2—C3—C4	−0.3 (2)	N1—C15—C20—C19	−177.60 (14)
C1—C2—C3—C4	−178.78 (12)	N2—C14—C21—C26	39.32 (19)
C2—C3—C4—O2	−179.35 (12)	C12—C14—C21—C26	−143.64 (14)
C2—C3—C4—C5	1.0 (2)	N2—C14—C21—C22	−137.32 (14)
O2—C4—C5—O3	0.76 (17)	C12—C14—C21—C22	39.7 (2)
C3—C4—C5—O3	−179.53 (12)	C26—C21—C22—C23	−0.7 (2)
O2—C4—C5—C6	179.67 (13)	C14—C21—C22—C23	176.01 (13)
C3—C4—C5—C6	−0.6 (2)	C21—C22—C23—C24	0.2 (2)
O3—C5—C6—C7	178.41 (14)	C22—C23—C24—C25	0.2 (2)
C4—C5—C6—C7	−0.4 (2)	C23—C24—C25—C26	0.0 (2)
C3—C2—C7—C6	−0.7 (2)	C24—C25—C26—C21	−0.5 (2)
C1—C2—C7—C6	177.69 (14)	C22—C21—C26—C25	0.8 (2)
C5—C6—C7—C2	1.1 (2)	C14—C21—C26—C25	−175.86 (13)
O1—C1—C8—C9	17.3 (2)	C12—C13—N1—N2	0.22 (16)
C2—C1—C8—C9	−162.38 (14)	C12—C13—N1—C15	−176.70 (13)
C1—C8—C9—C12	−177.91 (13)	C16—C15—N1—C13	21.0 (2)
C8—C9—C12—C13	28.4 (2)	C20—C15—N1—C13	−160.54 (14)
C8—C9—C12—C14	−154.16 (15)	C16—C15—N1—N2	−155.67 (12)
C14—C12—C13—N1	0.05 (15)	C20—C15—N1—N2	22.77 (19)
C9—C12—C13—N1	178.01 (13)	C12—C14—N2—N1	0.43 (15)
C13—C12—C14—N2	−0.31 (16)	C21—C14—N2—N1	177.95 (11)
C9—C12—C14—N2	−178.22 (13)	C13—N1—N2—C14	−0.40 (15)
C13—C12—C14—C21	−177.54 (13)	C15—N1—N2—C14	176.77 (12)
C9—C12—C14—C21	4.5 (2)	C3—C4—O2—C10	6.1 (2)
C20—C15—C16—C17	−0.7 (2)	C5—C4—O2—C10	−174.22 (14)
N1—C15—C16—C17	177.73 (13)	C6—C5—O3—C11	−7.3 (2)
C15—C16—C17—C18	−0.2 (2)	C4—C5—O3—C11	171.50 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O2ⁱ	0.94	2.34	3.2648 (19)	169

Symmetry code: (i) −x+1, −y+2, −z+1.

Acknowledgements

This work was supported by a Dongduk Women's University grant.

References

Bruker (2012). APEX2 and SAINT. Bruker AXS Inc. Madison, Wisconsin, USA. Google Scholar
Brullo, C., Rapetti, F. & Bruno, O. (2020). Molecules, 25, 3457. Web of Science CrossRef PubMed Google Scholar
Ebenezer, O., Shapi, M. & Tuszynski, J. (2022). Biomedicines, 10, 1124. Web of Science CrossRef PubMed Google Scholar
Elkanzi, N. A. A., Hrichi, H., Alolayan, R. A., Derafa, W., Zahou, F. M. & Bakr, R. B. (2022). ACS Omega, 7, 27769–27786. Web of Science CrossRef CAS PubMed Google Scholar
Krause, L., Herbst-Irmer, R., Sheldrick, G. M. & Stalke, D. (2015). J. Appl. Cryst. 48, 3–10. Web of Science CSD CrossRef ICSD CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sivaramakarthikeyan, R., Iniyaval, S., Saravanan, V., Lim, W.-M., Mai, C.-W. & Ramalingan, C. (2020). ACS Omega, 5, 10089–10098. Web of Science CrossRef CAS PubMed Google Scholar
Sung, J. (2019). IUCrData, 4, x191281. Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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