2-(7-Methyl-3-oxo-1-phenyl­perhydro­naphthalen-4a-yl)malononitrile

Kang, T.-R.; Chen, L.-M.

doi:10.1107/S1600536809047175

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3065

doi:10.1107/S1600536809047175

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2-(7-Methyl-3-oxo-1-phenylperhydronaphthalen-4a-yl)malononitrile

Tai-Ran Kang ^a ^* and Lian-Mei Chen ^a

^aCollege of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China
^*Correspondence e-mail: kangtairan@yahoo.com.cn

(Received 6 November 2009; accepted 8 November 2009; online 11 November 2009)

In the title compound, C₂₀H₂₂N₂O, both cyclohexane rings adopt chair conformations. Weak C—H⋯N and C—H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For the use of malononitrile-containing compounds as building blocks in organic synthesis, see: Magdi et al. (2003 ); Michail & Sergey (2008 ); Zhang et al. (2008 ). For a related structure, see: Zhou et al. (2007 ).

Experimental

Crystal data

C₂₀H₂₂N₂O
M_r = 306.40
Monoclinic, P 2₁
a = 11.575 (2) Å
b = 6.0907 (12) Å
c = 12.276 (3) Å
β = 101.38 (3)°
V = 848.4 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 113 K
0.25 × 0.24 × 0.21 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: none
7044 measured reflections
2194 independent reflections
1479 reflections with I > 2σ(I)
R_int = 0.063

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.083
S = 1.04
2194 reflections
209 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9⋯O1ⁱ	0.95	2.54	3.451 (3)	162
C12—H12A⋯O1ⁱⁱ	0.99	2.35	3.159 (2)	138
C18—H18⋯N1ⁱⁱⁱ	1.00	2.36	3.306 (3)	157
Symmetry codes: (i) x, y-1, z; (ii) $[-x+1, y-{\script{1\over 2}}, -z]$ ; (iii) $[-x+1, y-{\script{1\over 2}}, -z+1]$ .

Data collection: CrystalClear (Rigaku/MSC, 2005 ); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809047175/xu2670sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809047175/xu2670Isup2.hkl

checkCIF report

Comment top

Malononitrile derivatives are useful intermediates in organic synthesis (Michail et al. 2008; Zhang et al. 2008; Zhou et al. 2007). Their potential applications are used for the preparation of heterocyclic ring compounds (Magdi et al. 2003). As a part of our interest in the synthsis of some complex ring systems, we investigated the title compound, (I), which is a potential precursor in the preparation of multifunctional tricyclic compound. We report herein the crystal structure of the title compound.

The molecular structure of (I) is shown in Fig. 1. Bond lengths and angles in (I) are normal. Two six membered rings (cyclohexanone and cyclohexane) adopt an chair conformation. The crystal packing is stabilized by C—H···N and C—H···0 hydrogen bonding (Table 1).

Related literature top

For the use of malononitrile-containing compounds as building blocks in organic synthesis, see: Magdi et al. (2003); Michail & Sergey (2008); Zhang et al. (2008). For a related structure, see: Zhou et al. (2007).

Experimental top

2-(4-methylcyclohexylidene)malononitrile (0.16 g, 1 mmol), (E)-4-phenylbut-3-en-2-one (0.175 g, 1.2 mmol), 9S-amino-9-deoxyepiquinine (0.065 g, 0.2 mmol), 2,2,2-trifluoroacetic acid (0.029 g, 0.4 mmol) and N-ethyl-N-isopropylpropan-2-amine (0.023 g, 0.15 mmol) were stirred in THF (3 ml) at 298 K for 110 h. Then the reaction was quenched by adding 1 mol/L HCl (5 ml). The mixture was extracted with ethyl acetate (20 ml), dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure and flash chromatography on silica gel gave the pure compound as a white solid. Colorless single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation the mixture solvents of ethyl acetate and petroleum ether.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) with 30% probability displacement ellipsoids (arbitrary spheres for H atoms).

2-(7-Methyl-3-oxo-1-phenylperhydronaphthalen-4a-yl)malononitrile top

Crystal data top

C₂₀H₂₂N₂O	F(000) = 328
M_r = 306.40	D_x = 1.199 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2724 reflections
a = 11.575 (2) Å	θ = 3.4–27.9°
b = 6.0907 (12) Å	µ = 0.07 mm⁻¹
c = 12.276 (3) Å	T = 113 K
β = 101.38 (3)°	Block, colourless
V = 848.4 (3) Å³	0.25 × 0.24 × 0.21 mm
Z = 2

Data collection top

Rigaku Saturn CCD area-detector diffractometer	1479 reflections with I > 2σ(I)
Radiation source: rotating anode	R_int = 0.063
Confocal monochromator	θ_max = 27.9°, θ_min = 3.4°
Detector resolution: 7.31 pixels mm^-1	h = −15→15
ω and ϕ scans	k = −7→7
7044 measured reflections	l = −14→16
2194 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.083	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.021P)²] where P = (F_o² + 2F_c²)/3
2194 reflections	(Δ/σ)_max < 0.001
209 parameters	Δρ_max = 0.22 e Å⁻³
1 restraint	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₂₀H₂₂N₂O	V = 848.4 (3) Å³
M_r = 306.40	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 11.575 (2) Å	µ = 0.07 mm⁻¹
b = 6.0907 (12) Å	T = 113 K
c = 12.276 (3) Å	0.25 × 0.24 × 0.21 mm
β = 101.38 (3)°

Data collection top

Rigaku Saturn CCD area-detector diffractometer	1479 reflections with I > 2σ(I)
7044 measured reflections	R_int = 0.063
2194 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	1 restraint
wR(F²) = 0.083	H-atom parameters constrained
S = 1.04	Δρ_max = 0.22 e Å⁻³
2194 reflections	Δρ_min = −0.24 e Å⁻³
209 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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.

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

	x	y	z	U_iso*/U_eq
O1	0.59916 (14)	0.6258 (3)	0.05489 (13)	0.0319 (4)
N1	0.3799 (2)	0.3869 (4)	0.41898 (18)	0.0389 (6)
N2	0.40092 (18)	−0.1712 (4)	0.21854 (19)	0.0354 (6)
C1	0.61036 (19)	0.2632 (4)	0.27728 (18)	0.0183 (5)
C2	0.71015 (19)	0.1075 (4)	0.25731 (17)	0.0193 (5)
H2	0.6728	−0.0267	0.2185	0.023*
C3	0.7857 (2)	0.2188 (4)	0.18092 (18)	0.0204 (5)
H3	0.8198	0.3556	0.2194	0.025*
C4	0.8884 (2)	0.0760 (4)	0.16412 (18)	0.0223 (6)
C5	1.0035 (2)	0.1440 (4)	0.20656 (19)	0.0272 (6)
H5	1.0169	0.2812	0.2437	0.033*
C6	1.0987 (2)	0.0139 (5)	0.1952 (2)	0.0330 (7)
H6	1.1766	0.0634	0.2239	0.040*
C7	1.0812 (2)	−0.1863 (5)	0.1427 (2)	0.0329 (7)
H7	1.1466	−0.2765	0.1367	0.040*
C8	0.9677 (2)	−0.2551 (4)	0.0988 (2)	0.0330 (6)
H8	0.9550	−0.3919	0.0612	0.040*
C9	0.8720 (2)	−0.1242 (4)	0.10967 (19)	0.0283 (6)
H9	0.7943	−0.1729	0.0793	0.034*
C10	0.7070 (2)	0.2892 (4)	0.07005 (18)	0.0261 (6)
H10A	0.7555	0.3644	0.0234	0.031*
H10B	0.6711	0.1578	0.0294	0.031*
C11	0.6119 (2)	0.4407 (4)	0.09118 (19)	0.0239 (6)
C12	0.5360 (2)	0.3476 (4)	0.16652 (17)	0.0220 (5)
H12A	0.4884	0.2251	0.1281	0.026*
H12B	0.4811	0.4625	0.1824	0.026*
C13	0.7868 (2)	0.0355 (4)	0.36900 (18)	0.0207 (5)
H13A	0.7386	−0.0562	0.4094	0.025*
H13B	0.8525	−0.0563	0.3540	0.025*
C14	0.8377 (2)	0.2275 (4)	0.44301 (19)	0.0233 (6)
H14	0.8921	0.3100	0.4039	0.028*
C15	0.7405 (2)	0.3855 (4)	0.46116 (18)	0.0226 (5)
H15A	0.7768	0.5170	0.5013	0.027*
H15B	0.6912	0.3132	0.5080	0.027*
C16	0.6622 (2)	0.4565 (4)	0.35109 (18)	0.0207 (5)
H16A	0.7093	0.5488	0.3097	0.025*
H16B	0.5969	0.5477	0.3673	0.025*
C17	0.9091 (2)	0.1482 (5)	0.55366 (19)	0.0341 (7)
H17A	0.8580	0.0640	0.5932	0.051*
H17B	0.9414	0.2750	0.5987	0.051*
H17C	0.9737	0.0546	0.5403	0.051*
C18	0.52557 (19)	0.1314 (4)	0.33947 (18)	0.0213 (5)
H18	0.5755	0.0568	0.4048	0.026*
C19	0.4415 (2)	0.2767 (4)	0.38201 (19)	0.0255 (6)
C20	0.4563 (2)	−0.0388 (4)	0.2708 (2)	0.0235 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0308 (10)	0.0322 (11)	0.0298 (9)	0.0017 (9)	−0.0009 (8)	0.0110 (9)
N1	0.0373 (14)	0.0422 (15)	0.0404 (13)	−0.0023 (12)	0.0155 (11)	−0.0142 (12)
N2	0.0259 (12)	0.0288 (14)	0.0513 (14)	−0.0010 (11)	0.0073 (11)	−0.0060 (12)
C1	0.0163 (12)	0.0199 (13)	0.0181 (11)	0.0011 (10)	0.0022 (9)	0.0019 (10)
C2	0.0195 (12)	0.0195 (13)	0.0180 (11)	−0.0005 (11)	0.0010 (9)	−0.0021 (11)
C3	0.0183 (12)	0.0233 (14)	0.0196 (11)	0.0020 (11)	0.0035 (10)	0.0007 (11)
C4	0.0211 (13)	0.0274 (16)	0.0196 (12)	−0.0006 (12)	0.0070 (10)	0.0021 (11)
C5	0.0239 (13)	0.0336 (15)	0.0247 (12)	−0.0001 (13)	0.0063 (10)	0.0019 (12)
C6	0.0208 (14)	0.0470 (19)	0.0315 (14)	0.0015 (13)	0.0059 (11)	0.0048 (13)
C7	0.0273 (15)	0.0419 (19)	0.0326 (14)	0.0129 (14)	0.0133 (12)	0.0085 (13)
C8	0.0396 (17)	0.0318 (15)	0.0309 (14)	0.0053 (14)	0.0150 (13)	−0.0003 (13)
C9	0.0258 (14)	0.0293 (15)	0.0309 (14)	0.0007 (12)	0.0086 (11)	−0.0004 (12)
C10	0.0274 (14)	0.0332 (15)	0.0192 (12)	0.0010 (12)	0.0080 (10)	0.0044 (11)
C11	0.0213 (13)	0.0314 (16)	0.0164 (11)	0.0014 (12)	−0.0030 (10)	0.0017 (11)
C12	0.0190 (12)	0.0245 (14)	0.0200 (12)	0.0018 (12)	−0.0019 (10)	−0.0005 (11)
C13	0.0181 (12)	0.0232 (14)	0.0204 (12)	0.0028 (11)	0.0030 (10)	0.0020 (10)
C14	0.0193 (12)	0.0283 (14)	0.0211 (12)	0.0004 (11)	0.0012 (10)	0.0020 (11)
C15	0.0204 (13)	0.0235 (14)	0.0224 (12)	0.0002 (11)	0.0001 (10)	−0.0021 (11)
C16	0.0190 (12)	0.0195 (13)	0.0232 (12)	0.0018 (11)	0.0032 (10)	−0.0012 (11)
C17	0.0278 (14)	0.0434 (17)	0.0275 (13)	0.0072 (14)	−0.0036 (11)	−0.0005 (13)
C18	0.0178 (11)	0.0218 (12)	0.0239 (12)	0.0023 (11)	0.0031 (10)	0.0000 (11)
C19	0.0228 (13)	0.0311 (15)	0.0237 (12)	−0.0063 (13)	0.0070 (11)	−0.0056 (12)
C20	0.0192 (13)	0.0230 (14)	0.0295 (14)	0.0035 (12)	0.0081 (11)	0.0008 (12)

Geometric parameters (Å, º) top

O1—C11	1.211 (3)	C10—C11	1.498 (3)
N1—C19	1.137 (3)	C10—H10A	0.9900
N2—C20	1.145 (3)	C10—H10B	0.9900
C1—C16	1.534 (3)	C11—C12	1.506 (3)
C1—C12	1.547 (3)	C12—H12A	0.9900
C1—C2	1.551 (3)	C12—H12B	0.9900
C1—C18	1.577 (3)	C13—C14	1.526 (3)
C2—C13	1.543 (3)	C13—H13A	0.9900
C2—C3	1.558 (3)	C13—H13B	0.9900
C2—H2	1.0000	C14—C17	1.522 (3)
C3—C4	1.520 (3)	C14—C15	1.530 (3)
C3—C10	1.542 (3)	C14—H14	1.0000
C3—H3	1.0000	C15—C16	1.533 (3)
C4—C9	1.386 (3)	C15—H15A	0.9900
C4—C5	1.395 (3)	C15—H15B	0.9900
C5—C6	1.386 (3)	C16—H16A	0.9900
C5—H5	0.9500	C16—H16B	0.9900
C6—C7	1.375 (4)	C17—H17A	0.9800
C6—H6	0.9500	C17—H17B	0.9800
C7—C8	1.384 (4)	C17—H17C	0.9800
C7—H7	0.9500	C18—C20	1.470 (3)
C8—C9	1.392 (3)	C18—C19	1.484 (3)
C8—H8	0.9500	C18—H18	1.0000
C9—H9	0.9500

C16—C1—C12	110.45 (19)	C11—C12—C1	111.99 (18)
C16—C1—C2	110.22 (18)	C11—C12—H12A	109.2
C12—C1—C2	111.52 (17)	C1—C12—H12A	109.2
C16—C1—C18	108.26 (17)	C11—C12—H12B	109.2
C12—C1—C18	107.66 (17)	C1—C12—H12B	109.2
C2—C1—C18	108.61 (18)	H12A—C12—H12B	107.9
C13—C2—C1	110.43 (16)	C14—C13—C2	113.48 (19)
C13—C2—C3	111.48 (18)	C14—C13—H13A	108.9
C1—C2—C3	110.66 (18)	C2—C13—H13A	108.9
C13—C2—H2	108.1	C14—C13—H13B	108.9
C1—C2—H2	108.1	C2—C13—H13B	108.9
C3—C2—H2	108.1	H13A—C13—H13B	107.7
C4—C3—C10	112.40 (17)	C17—C14—C13	111.5 (2)
C4—C3—C2	112.31 (18)	C17—C14—C15	110.78 (19)
C10—C3—C2	110.42 (18)	C13—C14—C15	111.13 (19)
C4—C3—H3	107.1	C17—C14—H14	107.8
C10—C3—H3	107.1	C13—C14—H14	107.8
C2—C3—H3	107.1	C15—C14—H14	107.8
C9—C4—C5	118.1 (2)	C14—C15—C16	111.88 (18)
C9—C4—C3	122.2 (2)	C14—C15—H15A	109.2
C5—C4—C3	119.7 (2)	C16—C15—H15A	109.2
C6—C5—C4	120.8 (2)	C14—C15—H15B	109.2
C6—C5—H5	119.6	C16—C15—H15B	109.2
C4—C5—H5	119.6	H15A—C15—H15B	107.9
C7—C6—C5	120.5 (2)	C15—C16—C1	113.49 (18)
C7—C6—H6	119.7	C15—C16—H16A	108.9
C5—C6—H6	119.7	C1—C16—H16A	108.9
C6—C7—C8	119.4 (2)	C15—C16—H16B	108.9
C6—C7—H7	120.3	C1—C16—H16B	108.9
C8—C7—H7	120.3	H16A—C16—H16B	107.7
C7—C8—C9	120.1 (3)	C14—C17—H17A	109.5
C7—C8—H8	119.9	C14—C17—H17B	109.5
C9—C8—H8	119.9	H17A—C17—H17B	109.5
C4—C9—C8	120.9 (2)	C14—C17—H17C	109.5
C4—C9—H9	119.5	H17A—C17—H17C	109.5
C8—C9—H9	119.5	H17B—C17—H17C	109.5
C11—C10—C3	110.17 (18)	C20—C18—C19	107.53 (19)
C11—C10—H10A	109.6	C20—C18—C1	113.71 (18)
C3—C10—H10A	109.6	C19—C18—C1	112.4 (2)
C11—C10—H10B	109.6	C20—C18—H18	107.7
C3—C10—H10B	109.6	C19—C18—H18	107.7
H10A—C10—H10B	108.1	C1—C18—H18	107.7
O1—C11—C10	123.4 (2)	N1—C19—C18	177.1 (3)
O1—C11—C12	122.2 (2)	N2—C20—C18	178.7 (2)
C10—C11—C12	114.3 (2)

C16—C1—C2—C13	54.0 (2)	C3—C10—C11—O1	120.9 (2)
C12—C1—C2—C13	177.03 (19)	C3—C10—C11—C12	−56.3 (3)
C18—C1—C2—C13	−64.5 (2)	O1—C11—C12—C1	−124.1 (2)
C16—C1—C2—C3	−69.9 (2)	C10—C11—C12—C1	53.1 (3)
C12—C1—C2—C3	53.1 (2)	C16—C1—C12—C11	72.3 (2)
C18—C1—C2—C3	171.61 (17)	C2—C1—C12—C11	−50.7 (3)
C13—C2—C3—C4	53.7 (2)	C18—C1—C12—C11	−169.7 (2)
C1—C2—C3—C4	177.04 (18)	C1—C2—C13—C14	−55.3 (2)
C13—C2—C3—C10	−179.95 (19)	C3—C2—C13—C14	68.2 (2)
C1—C2—C3—C10	−56.6 (2)	C2—C13—C14—C17	178.06 (19)
C10—C3—C4—C9	−60.6 (3)	C2—C13—C14—C15	53.9 (2)
C2—C3—C4—C9	64.7 (3)	C17—C14—C15—C16	−176.4 (2)
C10—C3—C4—C5	120.9 (2)	C13—C14—C15—C16	−51.9 (3)
C2—C3—C4—C5	−113.8 (2)	C14—C15—C16—C1	53.7 (3)
C9—C4—C5—C6	−0.5 (3)	C12—C1—C16—C15	−178.17 (18)
C3—C4—C5—C6	178.1 (2)	C2—C1—C16—C15	−54.5 (2)
C4—C5—C6—C7	−0.7 (4)	C18—C1—C16—C15	64.2 (2)
C5—C6—C7—C8	1.5 (4)	C16—C1—C18—C20	171.35 (19)
C6—C7—C8—C9	−1.2 (4)	C12—C1—C18—C20	51.9 (2)
C5—C4—C9—C8	0.8 (3)	C2—C1—C18—C20	−69.0 (2)
C3—C4—C9—C8	−177.8 (2)	C16—C1—C18—C19	48.9 (2)
C7—C8—C9—C4	0.1 (4)	C12—C1—C18—C19	−70.5 (2)
C4—C3—C10—C11	−176.4 (2)	C2—C1—C18—C19	168.59 (18)
C2—C3—C10—C11	57.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1ⁱ	0.95	2.54	3.451 (3)	162
C12—H12A···O1ⁱⁱ	0.99	2.35	3.159 (2)	138
C18—H18···N1ⁱⁱⁱ	1.00	2.36	3.306 (3)	157

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

Experimental details

Crystal data
Chemical formula	C₂₀H₂₂N₂O
M_r	306.40
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	113
a, b, c (Å)	11.575 (2), 6.0907 (12), 12.276 (3)
β (°)	101.38 (3)
V (Å³)	848.4 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.25 × 0.24 × 0.21

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7044, 2194, 1479
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.083, 1.04
No. of reflections	2194
No. of parameters	209
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.24

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O1ⁱ	0.95	2.54	3.451 (3)	161.7
C12—H12A···O1ⁱⁱ	0.99	2.35	3.159 (2)	138.0
C18—H18···N1ⁱⁱⁱ	1.00	2.36	3.306 (3)	157.0

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

Acknowledgements

The diffraction data were collected at the Centre for Testing and Analysis, Sichuan University. We acknowledge financial support from China West Normal University (No 412374).

References

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