Ethyl 2-cyano-2-{(Z)-2-[2,2-di­cyano-1-(4-methyl­phen­yl)eth­yl]cyclo­hexyl­idene}acetate

Sivapriya, S.; Priyanka, S.; Gopalakrishnan, M.; Manikandan, H.; Selvanayagam, S.

doi:10.1107/S2414314621005009

organic compounds

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ISSN: 2414-3146

Volume 6| Part 5| May 2021| x210500

https://doi.org/10.1107/S2414314621005009

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Ethyl 2-cyano-2-{(Z)-2-[2,2-dicyano-1-(4-methylphenyl)ethyl]cyclohexylidene}acetate

S. Sivapriya,^a S. Priyanka,^a M. Gopalakrishnan,^a H. Manikandan ^a ^* and S. Selvanayagam ^b

^aDepartment of Chemistry, Annamalai University, Annamalainagar, Chidambaram 608 002, India, and ^bPG & Research Department of Physics, Government Arts College, Melur 625 106, India
^*Correspondence e-mail: profmani.au@gmail.com

Edited by M. Bolte, Goethe-Universität Frankfurt, Germany (Received 29 March 2021; accepted 11 May 2021; online 14 May 2021)

In the title compound, C₂₂H₂₃N₃O₂, the cyclohexane ring adopts a chair conformation. The methylphenyl ring is oriented at an angle of 36.2 (1)° with respect to the best plane of cyclohexane moiety. In the crystal, molecules associate via C—H⋯N hydrogen bonds, forming a three-dimensional network.

Keywords: crystal structure; cyclohexylidene derivatives; chair conformation; intermolecular C—H⋯N hydrogen bonds.

CCDC reference: 2057162

Structure description

Cyclohexylidene derivatives possess a wide range of biological activities including antibacterial (Gupta & Narayana, 1997 ), antiviral (Ulusoy Guzeldemirci et al., 2016 ), antituberculatic and anti-inflammatory (Kabir et al., 2008 ). As part of our studies in this area, we have undertaken a single-crystal X-ray diffraction study for the title compound, and the results are presented here.

The methylphenyl ring is oriented at an angle of 36.2 (1)° with respect to the best plane of cyclohexane moiety. The cyclohexane ring adopts a chair conformation, the puckering parameters (Cremer & Pople, 1975 ) are: q₂ = 0.001 (1) Å, q₃ = −0.562 (2) Å, Q_T = 0.562 (2) Å and θ = 179.0 (1)°. Atoms C1 and C4 deviate by 0.681 (1) and −0.652 (1) Å, respectively, from the least-squares plane through the remaining four atoms. An intramolecular C—H⋯O hydrogen bond is observed (Table 1), which generates an S(6) ring (Fig. 1).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O1	0.98	2.23	3.001 (2)	135
C5—H5A⋯N1ⁱ	0.97	2.57	3.536 (3)	172
C8—H8⋯N3ⁱⁱ	0.98	2.27	3.221 (2)	163
Symmetry codes: (i) ; (ii) .

Figure 1
The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level. The intramolecular C—H⋯O hydrogen bond is shown as a dashed line.

In the crystal, molecules associate via pairwise C5—H5A⋯N1ⁱ hydrogen bonds into inversion dimers with an R₂²(16) loop motif. In addition, C8—H8⋯N3ⁱⁱ hydrogen bonds form a R₂²(16) graph-set motif (Fig. 2).

Figure 2
The crystal packing of the title compound viewed down the a axis. The C—H⋯N hydrogen bonds (see Table 1

) are shown as dashed lines. For clarity, H atoms not involved in these interactions have been omitted.

The two-dimensional fingerprint plots (Spackman & Jayatilaka, 2009 ) of the molecule, created using Crystal Explorer 17 (Turner et al., 2017 ) for the contacts contributing to the Hirshfeld surface are shown in Figs. 3–5 . The analysis reveals that H⋯H contacts (45.7%) and N⋯H/H⋯N contacts (29.8%) are the main contributors to the crystal packing, followed by C⋯H/H⋯C (14%) and O⋯H/H⋯O (7.8%) contacts.

Figure 3
The two-dimensional fingerprint plot for the title compound depicting the overall contribution by the various contacts.

Figure 4
The two-dimensional fingerprint plot for the title compound depicting the contribution of the N⋯H contacts.

Figure 5
The two-dimensional fingerprint plot for the title compound depicting the contribution of the C⋯H contacts.

Synthesis and crystallization

A mixture of 2-amino-4-(p-tolyl)octahydronaphthalene-1,3,3(2H)-tricarbonitrile (0.01 mol), formic acid (5 mL) and a catalytic amount of concentrated HCl was refluxed for 16 h and the reaction mixture was allowed to cool. The reaction mixture was poured onto crushed ice and the solid that separated was filtered, dried and recrystallized using ethanol and water as mixed solvents.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₂₂H₂₃N₃O₂
M_r	361.43
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	296
a, b, c (Å)	8.4465 (3), 10.2960 (4), 12.1699 (4)
α, β, γ (°)	91.240 (1), 95.072 (1), 92.102 (1)
V (Å³)	1053.17 (7)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.07
Crystal size (mm)	0.24 × 0.21 × 0.19

Data collection
Diffractometer	Bruker SMART APEX CCD
No. of measured, independent and observed [I > 2σ(I)] reflections	28133, 6098, 4212
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.704

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.211, 0.97
No. of reflections	6098
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.31
Computer programs: SMART and, SAINT (Bruker, 2008 ), SHELXS97 (Sheldrick, 2008 ), SHELXL2018/3 (Sheldrick, 2008 ), ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2020 ).

Structural data

CCDC reference: 2057162

Crystal structure: contains datablocks I, shelx. DOI: https://doi.org/10.1107/S2414314621005009/bt4111sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314621005009/bt4111Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314621005009/bt4111Isup3.cml

checkCIF report

Computing details top

Data collection: SMART (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2020); software used to prepare material for publication: SHELXL2018/3 (Sheldrick, 2015) and PLATON (Spek, 2020).

Ethyl 2-cyano-2-{(Z)-2-[2,2-dicyano-1-(4-methylphenyl)ethyl]cyclohexylidene}acetate top

Crystal data top

C₂₂H₂₃N₃O₂	Z = 2
M_r = 361.43	F(000) = 384
Triclinic, P1	D_x = 1.140 Mg m⁻³
a = 8.4465 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.2960 (4) Å	Cell parameters from 18428 reflections
c = 12.1699 (4) Å	θ = 2.8–28.2°
α = 91.240 (1)°	µ = 0.07 mm⁻¹
β = 95.072 (1)°	T = 296 K
γ = 92.102 (1)°	Block, colourless
V = 1053.17 (7) Å³	0.24 × 0.21 × 0.19 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	R_int = 0.033
Radiation source: fine-focus sealed tube	θ_max = 30.0°, θ_min = 2.6°
ω and φ scans	h = −11→11
28133 measured reflections	k = −14→14
6098 independent reflections	l = −16→17
4212 reflections with I > 2σ(I)

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)] = 0.064	H-atom parameters constrained
wR(F²) = 0.211	w = 1/[σ²(F_o²) + (0.1037P)² + 0.3202P] where P = (F_o² + 2F_c²)/3
S = 0.97	(Δ/σ)_max < 0.001
6098 reflections	Δρ_max = 0.38 e Å⁻³
244 parameters	Δρ_min = −0.31 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.

Refinement. H atoms were placed in idealized positions and allowed to ride on their parent atoms: C—H = 0.93–0.98 Å, with U_iso(H) = 1.5U_eq(C) for methyl H atoms and 1.2U_eq(C) for other H atoms.

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

	x	y	z	U_iso*/U_eq
O1	0.2013 (2)	0.55320 (15)	0.86132 (11)	0.0772 (4)
O2	0.0185 (2)	0.42057 (16)	0.77154 (13)	0.0819 (5)
N1	−0.1230 (3)	1.0587 (2)	0.60489 (18)	0.0857 (6)
N2	−0.0870 (3)	0.7604 (3)	0.8407 (2)	0.1067 (8)
N3	0.11934 (19)	0.34667 (15)	0.52121 (14)	0.0616 (4)
C1	0.30484 (18)	0.75924 (14)	0.70937 (13)	0.0443 (3)
H1	0.285441	0.734845	0.784544	0.053*
C2	0.4861 (2)	0.78324 (19)	0.70392 (18)	0.0628 (5)
H2A	0.521171	0.859385	0.749172	0.075*
H2B	0.541326	0.709455	0.734562	0.075*
C3	0.5315 (2)	0.8033 (2)	0.5874 (2)	0.0732 (6)
H3A	0.486124	0.882452	0.559229	0.088*
H3B	0.646316	0.813127	0.588507	0.088*
C4	0.4726 (2)	0.6896 (2)	0.5118 (2)	0.0700 (5)
H4A	0.528715	0.612669	0.534317	0.084*
H4B	0.495422	0.708172	0.436902	0.084*
C5	0.2929 (2)	0.66303 (15)	0.51486 (13)	0.0489 (4)
H5A	0.235573	0.735033	0.482858	0.059*
H5B	0.260103	0.585006	0.471424	0.059*
C6	0.25320 (16)	0.64621 (13)	0.63136 (12)	0.0411 (3)
C7	0.21454 (17)	0.88396 (13)	0.68062 (12)	0.0417 (3)
H7	0.244434	0.910752	0.608248	0.050*
C8	0.03147 (19)	0.85589 (15)	0.66844 (14)	0.0488 (4)
H8	0.009240	0.789898	0.609301	0.059*
C9	−0.0339 (2)	0.8042 (2)	0.76680 (19)	0.0646 (5)
C10	−0.0551 (2)	0.97122 (18)	0.63408 (15)	0.0576 (4)
C11	0.26493 (18)	0.99501 (14)	0.76145 (12)	0.0440 (3)
C12	0.2656 (3)	0.98255 (17)	0.87475 (14)	0.0602 (5)
H12	0.231616	0.904205	0.903138	0.072*
C13	0.3163 (3)	1.08555 (19)	0.94631 (15)	0.0662 (5)
H13	0.315364	1.074856	1.021940	0.079*
C14	0.3677 (2)	1.20274 (18)	0.90808 (16)	0.0602 (5)
C15	0.3642 (3)	1.21591 (18)	0.79527 (17)	0.0660 (5)
H15	0.397002	1.294798	0.767239	0.079*
C16	0.3129 (2)	1.11375 (16)	0.72261 (15)	0.0563 (4)
H16	0.310842	1.125603	0.646965	0.068*
C17	0.4252 (3)	1.3131 (2)	0.9871 (2)	0.0852 (7)
H17A	0.456292	1.387009	0.946141	0.128*
H17B	0.341186	1.335986	1.031229	0.128*
H17C	0.514778	1.286442	1.034240	0.128*
C18	0.18375 (18)	0.53484 (14)	0.66384 (12)	0.0437 (3)
C19	0.14525 (18)	0.43040 (14)	0.58413 (13)	0.0461 (3)
C20	0.1382 (2)	0.50714 (16)	0.77718 (15)	0.0548 (4)
C21	−0.0385 (4)	0.3775 (3)	0.8773 (3)	0.1121 (11)
H21A	0.051164	0.353762	0.927149	0.135*
H21B	−0.090609	0.448219	0.911649	0.135*
C22	−0.1466 (7)	0.2695 (6)	0.8578 (4)	0.230 (4)
H22A	−0.182981	0.242201	0.926523	0.345*
H22B	−0.235819	0.293629	0.809141	0.345*
H22C	−0.094368	0.199386	0.824606	0.345*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.1095 (12)	0.0724 (9)	0.0462 (7)	−0.0169 (8)	−0.0038 (7)	0.0028 (6)
O2	0.0936 (11)	0.0866 (10)	0.0649 (9)	−0.0352 (9)	0.0220 (8)	−0.0082 (7)
N1	0.0845 (13)	0.0805 (12)	0.0916 (14)	0.0291 (10)	−0.0066 (10)	0.0086 (10)
N2	0.0828 (14)	0.1213 (19)	0.122 (2)	0.0053 (13)	0.0354 (14)	0.0376 (16)
N3	0.0638 (9)	0.0504 (8)	0.0681 (10)	−0.0032 (6)	−0.0017 (7)	−0.0148 (7)
C1	0.0461 (7)	0.0394 (7)	0.0454 (7)	−0.0001 (5)	−0.0041 (6)	−0.0053 (6)
C2	0.0452 (8)	0.0555 (9)	0.0841 (13)	0.0001 (7)	−0.0095 (8)	−0.0148 (9)
C3	0.0482 (9)	0.0661 (11)	0.1056 (17)	−0.0106 (8)	0.0168 (10)	−0.0112 (11)
C4	0.0612 (11)	0.0656 (11)	0.0858 (14)	−0.0039 (9)	0.0272 (10)	−0.0125 (10)
C5	0.0544 (9)	0.0440 (7)	0.0484 (8)	−0.0004 (6)	0.0087 (6)	−0.0049 (6)
C6	0.0386 (7)	0.0381 (6)	0.0454 (7)	0.0034 (5)	−0.0021 (5)	−0.0044 (5)
C7	0.0458 (7)	0.0383 (7)	0.0396 (7)	−0.0001 (5)	−0.0014 (5)	−0.0057 (5)
C8	0.0475 (8)	0.0433 (7)	0.0537 (9)	0.0030 (6)	−0.0040 (6)	−0.0112 (6)
C9	0.0506 (9)	0.0612 (10)	0.0824 (13)	0.0027 (8)	0.0066 (9)	0.0061 (10)
C10	0.0557 (9)	0.0585 (10)	0.0568 (10)	0.0076 (8)	−0.0053 (7)	−0.0078 (8)
C11	0.0475 (8)	0.0391 (7)	0.0439 (7)	0.0001 (6)	−0.0020 (6)	−0.0071 (6)
C12	0.0866 (13)	0.0476 (8)	0.0446 (8)	−0.0081 (8)	0.0010 (8)	−0.0054 (7)
C13	0.0893 (14)	0.0608 (10)	0.0457 (9)	−0.0025 (9)	−0.0044 (9)	−0.0133 (8)
C14	0.0635 (10)	0.0509 (9)	0.0621 (10)	0.0011 (7)	−0.0111 (8)	−0.0184 (8)
C15	0.0853 (13)	0.0431 (8)	0.0664 (11)	−0.0135 (8)	−0.0021 (10)	−0.0064 (8)
C16	0.0739 (11)	0.0453 (8)	0.0480 (8)	−0.0082 (7)	0.0008 (8)	−0.0031 (7)
C17	0.1015 (17)	0.0665 (12)	0.0806 (15)	−0.0079 (12)	−0.0192 (12)	−0.0301 (11)
C18	0.0449 (7)	0.0394 (7)	0.0454 (7)	0.0007 (5)	−0.0015 (6)	−0.0044 (6)
C19	0.0447 (7)	0.0409 (7)	0.0515 (8)	0.0009 (6)	−0.0005 (6)	−0.0028 (6)
C20	0.0654 (10)	0.0459 (8)	0.0528 (9)	−0.0025 (7)	0.0055 (8)	−0.0002 (7)
C21	0.133 (3)	0.122 (2)	0.0823 (18)	−0.037 (2)	0.0367 (17)	0.0020 (16)
C22	0.243 (6)	0.294 (8)	0.152 (4)	−0.161 (6)	0.090 (4)	−0.004 (4)

Geometric parameters (Å, º) top

O1—C20	1.192 (2)	C8—C10	1.466 (2)
O2—C20	1.320 (2)	C8—C9	1.465 (3)
O2—C21	1.484 (3)	C8—H8	0.9800
N1—C10	1.132 (2)	C11—C16	1.380 (2)
N2—C9	1.135 (3)	C11—C12	1.387 (2)
N3—C19	1.143 (2)	C12—C13	1.388 (2)
C1—C6	1.5125 (19)	C12—H12	0.9300
C1—C7	1.548 (2)	C13—C14	1.372 (3)
C1—C2	1.550 (2)	C13—H13	0.9300
C1—H1	0.9800	C14—C15	1.380 (3)
C2—C3	1.518 (3)	C14—C17	1.511 (2)
C2—H2A	0.9700	C15—C16	1.391 (2)
C2—H2B	0.9700	C15—H15	0.9300
C3—C4	1.514 (3)	C16—H16	0.9300
C3—H3A	0.9700	C17—H17A	0.9600
C3—H3B	0.9700	C17—H17B	0.9600
C4—C5	1.537 (3)	C17—H17C	0.9600
C4—H4A	0.9700	C18—C19	1.441 (2)
C4—H4B	0.9700	C18—C20	1.495 (2)
C5—C6	1.498 (2)	C21—C22	1.415 (5)
C5—H5A	0.9700	C21—H21A	0.9700
C5—H5B	0.9700	C21—H21B	0.9700
C6—C18	1.351 (2)	C22—H22A	0.9600
C7—C11	1.5158 (18)	C22—H22B	0.9600
C7—C8	1.556 (2)	C22—H22C	0.9600
C7—H7	0.9800

C20—O2—C21	117.29 (18)	N2—C9—C8	177.5 (3)
C6—C1—C7	112.65 (11)	N1—C10—C8	178.2 (2)
C6—C1—C2	107.22 (13)	C16—C11—C12	117.76 (14)
C7—C1—C2	110.65 (13)	C16—C11—C7	119.73 (14)
C6—C1—H1	108.7	C12—C11—C7	122.51 (14)
C7—C1—H1	108.7	C11—C12—C13	120.84 (17)
C2—C1—H1	108.7	C11—C12—H12	119.6
C3—C2—C1	113.00 (15)	C13—C12—H12	119.6
C3—C2—H2A	109.0	C14—C13—C12	121.55 (18)
C1—C2—H2A	109.0	C14—C13—H13	119.2
C3—C2—H2B	109.0	C12—C13—H13	119.2
C1—C2—H2B	109.0	C13—C14—C15	117.60 (15)
H2A—C2—H2B	107.8	C13—C14—C17	120.90 (19)
C4—C3—C2	111.15 (17)	C15—C14—C17	121.50 (19)
C4—C3—H3A	109.4	C14—C15—C16	121.44 (17)
C2—C3—H3A	109.4	C14—C15—H15	119.3
C4—C3—H3B	109.4	C16—C15—H15	119.3
C2—C3—H3B	109.4	C11—C16—C15	120.78 (16)
H3A—C3—H3B	108.0	C11—C16—H16	119.6
C3—C4—C5	111.29 (15)	C15—C16—H16	119.6
C3—C4—H4A	109.4	C14—C17—H17A	109.5
C5—C4—H4A	109.4	C14—C17—H17B	109.5
C3—C4—H4B	109.4	H17A—C17—H17B	109.5
C5—C4—H4B	109.4	C14—C17—H17C	109.5
H4A—C4—H4B	108.0	H17A—C17—H17C	109.5
C6—C5—C4	110.22 (15)	H17B—C17—H17C	109.5
C6—C5—H5A	109.6	C6—C18—C19	119.19 (14)
C4—C5—H5A	109.6	C6—C18—C20	126.34 (13)
C6—C5—H5B	109.6	C19—C18—C20	114.46 (13)
C4—C5—H5B	109.6	N3—C19—C18	177.98 (17)
H5A—C5—H5B	108.1	O1—C20—O2	124.07 (18)
C18—C6—C5	121.57 (13)	O1—C20—C18	125.98 (17)
C18—C6—C1	123.37 (14)	O2—C20—C18	109.94 (15)
C5—C6—C1	114.98 (12)	C22—C21—O2	109.9 (3)
C11—C7—C1	111.82 (11)	C22—C21—H21A	109.7
C11—C7—C8	112.83 (12)	O2—C21—H21A	109.7
C1—C7—C8	111.14 (12)	C22—C21—H21B	109.7
C11—C7—H7	106.9	O2—C21—H21B	109.7
C1—C7—H7	106.9	H21A—C21—H21B	108.2
C8—C7—H7	106.9	C21—C22—H22A	109.5
C10—C8—C9	108.96 (15)	C21—C22—H22B	109.5
C10—C8—C7	111.69 (14)	H22A—C22—H22B	109.5
C9—C8—C7	114.82 (14)	C21—C22—H22C	109.5
C10—C8—H8	107.0	H22A—C22—H22C	109.5
C9—C8—H8	107.0	H22B—C22—H22C	109.5
C7—C8—H8	107.0

C6—C1—C2—C3	54.57 (19)	C8—C7—C11—C12	74.0 (2)
C7—C1—C2—C3	−68.63 (18)	C16—C11—C12—C13	−1.4 (3)
C1—C2—C3—C4	−56.0 (2)	C7—C11—C12—C13	178.39 (17)
C2—C3—C4—C5	54.3 (2)	C11—C12—C13—C14	−0.1 (3)
C3—C4—C5—C6	−53.9 (2)	C12—C13—C14—C15	1.3 (3)
C4—C5—C6—C18	−120.06 (16)	C12—C13—C14—C17	−178.9 (2)
C4—C5—C6—C1	56.71 (17)	C13—C14—C15—C16	−0.9 (3)
C7—C1—C6—C18	−117.15 (16)	C17—C14—C15—C16	179.3 (2)
C2—C1—C6—C18	120.89 (16)	C12—C11—C16—C15	1.8 (3)
C7—C1—C6—C5	66.15 (17)	C7—C11—C16—C15	−178.03 (16)
C2—C1—C6—C5	−55.82 (17)	C14—C15—C16—C11	−0.6 (3)
C6—C1—C7—C11	178.52 (12)	C5—C6—C18—C19	−0.8 (2)
C2—C1—C7—C11	−61.47 (17)	C1—C6—C18—C19	−177.25 (13)
C6—C1—C7—C8	51.44 (17)	C5—C6—C18—C20	−179.74 (15)
C2—C1—C7—C8	171.45 (13)	C1—C6—C18—C20	3.8 (2)
C11—C7—C8—C10	57.22 (18)	C21—O2—C20—O1	−0.9 (3)
C1—C7—C8—C10	−176.25 (13)	C21—O2—C20—C18	177.7 (2)
C11—C7—C8—C9	−67.48 (17)	C6—C18—C20—O1	−28.4 (3)
C1—C7—C8—C9	59.05 (17)	C19—C18—C20—O1	152.57 (19)
C1—C7—C11—C16	127.58 (17)	C6—C18—C20—O2	153.07 (17)
C8—C7—C11—C16	−106.25 (18)	C19—C18—C20—O2	−26.0 (2)
C1—C7—C11—C12	−52.2 (2)	C20—O2—C21—C22	−169.7 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1	0.98	2.23	3.001 (2)	135
C5—H5A···N1ⁱ	0.97	2.57	3.536 (3)	172
C8—H8···N3ⁱⁱ	0.98	2.27	3.221 (2)	163

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

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