organic compounds
1-Methyl-5-(4-methylphenyl)-3-oxocyclohexane-1-carbonitrile
aDepartment of Chemistry, Annamalai University, Annamalai Nagar 608 002, Tamil Nadu, India, bPG Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamil Nadu, India, and cInstitute of Organic Chemistry, University of Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland
*Correspondence e-mail: athiru@vsnl.net
In the title molecule, C15H17NO, the cyclohexane ring adopts a chair conformation. The cyano and methyl groups at position 1 have axial and equatorial orientations, respectively. The benzene ring has an equatorial orientation. A C—H⋯π interaction involving the benzene ring is found in the crystal structure.
Related literature
Subramanyam et al. (2007) have reported the of 3-cyano-3-methyl-5-phenylcyclohexane, in which the cyclohexane ring adopts a chair conformation.
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: COLLECT (Nonius, 2000); cell DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997); 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: PLATON (Spek, 2003).
Supporting information
10.1107/S1600536808009070/wn2249sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808009070/wn2249Isup2.hkl
A mixture of 5-4'-methylphenyl-3-methylcyclohex-2-enone (4.00 g, 0.02 mol), potassium cyanide (2.60 g, 0.04 mol), ammonium chloride (1.59 g, 0.03 mol), dimethylformamide (50 ml) and water (2 ml) was heated with stirring for 16-18 h at 353 K. The reaction mixture was cooled to room temperature and poured into water. The product was extracted with CH2Cl2 (3x10 ml) and the organic layer was dried, evaporated and purified by
(hexane-EtOAc, 4.5:1 v/v). The yield of the isolated product was 3.40 g (75%).H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.95 Å for Csp2, 0.98 Å for methyl C, 0.99 Å for methylene C and 1.00 Å for methine C; Uiso(H) = xUeq(carrier atom), where x = 1.5 for methyl and 1.2 for all other C atoms
Data collection: COLLECT (Nonius, 2000); cell
DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997); 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: PLATON (Spek, 2003).C15H17NO | F(000) = 976 |
Mr = 227.30 | Dx = 1.211 Mg m−3 |
Monoclinic, C2/c | Melting point: 376 K |
Hall symbol: -C 2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 23.4475 (5) Å | Cell parameters from 3933 reflections |
b = 6.0370 (1) Å | θ = 2.0–30.0° |
c = 21.0740 (5) Å | µ = 0.08 mm−1 |
β = 123.267 (1)° | T = 160 K |
V = 2494.22 (9) Å3 | Tablet, colourless |
Z = 8 | 0.25 × 0.20 × 0.10 mm |
Nonius KappaCCD area-detector diffractometer | 2682 reflections with I > 2σ(I) |
Radiation source: Nonius FR590 sealed tube generator | Rint = 0.054 |
Horizontally mounted graphite crystal monochromator | θmax = 30.1°, θmin = 2.1° |
Detector resolution: 9 pixels mm-1 | h = 0→32 |
ϕ and ω scans with κ offsets | k = 0→8 |
37687 measured reflections | l = −29→24 |
3640 independent reflections |
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.170 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0889P)2 + 1.0674P] where P = (Fo2 + 2Fc2)/3 |
3640 reflections | (Δ/σ)max < 0.001 |
154 parameters | Δρmax = 0.42 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
C15H17NO | V = 2494.22 (9) Å3 |
Mr = 227.30 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 23.4475 (5) Å | µ = 0.08 mm−1 |
b = 6.0370 (1) Å | T = 160 K |
c = 21.0740 (5) Å | 0.25 × 0.20 × 0.10 mm |
β = 123.267 (1)° |
Nonius KappaCCD area-detector diffractometer | 2682 reflections with I > 2σ(I) |
37687 measured reflections | Rint = 0.054 |
3640 independent reflections |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.170 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.42 e Å−3 |
3640 reflections | Δρmin = −0.27 e Å−3 |
154 parameters |
Experimental. Solvent used: ? Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.608 (1) Frames collected: 469 Seconds exposure per frame: 68 Degrees rotation per frame: 1.7 Crystal-Detector distance (mm): 30.0 |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
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. |
x | y | z | Uiso*/Ueq | ||
O3 | −0.15528 (6) | 0.46344 (19) | 0.25177 (7) | 0.0415 (4) | |
N12 | −0.08326 (7) | 0.6151 (2) | 0.47679 (8) | 0.0396 (4) | |
C1 | −0.11894 (7) | 0.9214 (2) | 0.37288 (8) | 0.0257 (4) | |
C2 | −0.16638 (7) | 0.8175 (3) | 0.29352 (8) | 0.0301 (4) | |
C3 | −0.13059 (7) | 0.6453 (2) | 0.27576 (7) | 0.0284 (4) | |
C4 | −0.06263 (7) | 0.7130 (2) | 0.28980 (8) | 0.0285 (4) | |
C5 | −0.01555 (6) | 0.8211 (2) | 0.36851 (7) | 0.0235 (3) | |
C6 | −0.05364 (7) | 1.0065 (2) | 0.37989 (8) | 0.0257 (4) | |
C11 | −0.15578 (8) | 1.1085 (3) | 0.38596 (10) | 0.0358 (5) | |
C12 | −0.09953 (7) | 0.7479 (2) | 0.43103 (8) | 0.0283 (4) | |
C15 | 0.24199 (7) | 1.0891 (3) | 0.40745 (9) | 0.0366 (5) | |
C51 | 0.05077 (6) | 0.8959 (2) | 0.37806 (7) | 0.0234 (3) | |
C52 | 0.10525 (7) | 0.7488 (2) | 0.40770 (7) | 0.0268 (4) | |
C53 | 0.16606 (7) | 0.8088 (2) | 0.41545 (8) | 0.0288 (4) | |
C54 | 0.17508 (7) | 1.0191 (3) | 0.39554 (8) | 0.0283 (4) | |
C55 | 0.12020 (7) | 1.1653 (2) | 0.36508 (9) | 0.0321 (4) | |
C56 | 0.05907 (7) | 1.1049 (2) | 0.35635 (9) | 0.0308 (4) | |
H2A | −0.20592 | 0.74844 | 0.29089 | 0.0361* | |
H2B | −0.18388 | 0.93583 | 0.25469 | 0.0361* | |
H4A | −0.07029 | 0.81889 | 0.24998 | 0.0341* | |
H4B | −0.03970 | 0.58069 | 0.28600 | 0.0341* | |
H5 | −0.00387 | 0.70502 | 0.40771 | 0.0282* | |
H6A | −0.06599 | 1.12360 | 0.34155 | 0.0308* | |
H6B | −0.02313 | 1.07305 | 0.43072 | 0.0308* | |
H11A | −0.16873 | 1.22489 | 0.34797 | 0.0537* | |
H11B | −0.12531 | 1.17052 | 0.43686 | 0.0537* | |
H11C | −0.19680 | 1.04942 | 0.38141 | 0.0537* | |
H15A | 0.27435 | 0.96550 | 0.42915 | 0.0549* | |
H15B | 0.26039 | 1.21551 | 0.44228 | 0.0549* | |
H15C | 0.23475 | 1.13160 | 0.35866 | 0.0549* | |
H52 | 0.10086 | 0.60508 | 0.42290 | 0.0321* | |
H53 | 0.20209 | 0.70396 | 0.43470 | 0.0345* | |
H55 | 0.12464 | 1.30917 | 0.34997 | 0.0384* | |
H56 | 0.02242 | 1.20775 | 0.33526 | 0.0370* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O3 | 0.0412 (6) | 0.0397 (6) | 0.0472 (7) | −0.0142 (5) | 0.0266 (5) | −0.0148 (5) |
N12 | 0.0409 (7) | 0.0425 (8) | 0.0396 (7) | −0.0060 (6) | 0.0248 (6) | 0.0051 (6) |
C1 | 0.0254 (6) | 0.0250 (6) | 0.0306 (7) | −0.0027 (5) | 0.0178 (6) | −0.0022 (5) |
C2 | 0.0233 (6) | 0.0366 (8) | 0.0285 (7) | −0.0015 (6) | 0.0130 (5) | −0.0014 (6) |
C3 | 0.0273 (7) | 0.0332 (8) | 0.0231 (7) | −0.0052 (5) | 0.0129 (5) | −0.0028 (5) |
C4 | 0.0283 (7) | 0.0303 (7) | 0.0304 (7) | −0.0032 (5) | 0.0184 (6) | −0.0045 (5) |
C5 | 0.0224 (6) | 0.0230 (6) | 0.0265 (6) | −0.0008 (5) | 0.0144 (5) | 0.0021 (5) |
C6 | 0.0258 (6) | 0.0246 (7) | 0.0301 (7) | −0.0042 (5) | 0.0176 (6) | −0.0030 (5) |
C11 | 0.0364 (8) | 0.0305 (8) | 0.0515 (9) | −0.0015 (6) | 0.0311 (7) | −0.0045 (7) |
C12 | 0.0258 (6) | 0.0329 (7) | 0.0303 (7) | −0.0071 (5) | 0.0181 (6) | −0.0048 (6) |
C15 | 0.0275 (7) | 0.0443 (9) | 0.0427 (9) | −0.0070 (6) | 0.0222 (7) | −0.0033 (7) |
C51 | 0.0229 (6) | 0.0248 (6) | 0.0241 (6) | −0.0018 (5) | 0.0140 (5) | 0.0003 (5) |
C52 | 0.0258 (6) | 0.0264 (7) | 0.0272 (7) | −0.0003 (5) | 0.0140 (5) | 0.0040 (5) |
C53 | 0.0232 (6) | 0.0332 (7) | 0.0281 (7) | 0.0030 (5) | 0.0128 (5) | 0.0034 (6) |
C54 | 0.0249 (6) | 0.0340 (7) | 0.0289 (7) | −0.0052 (5) | 0.0167 (6) | −0.0035 (5) |
C55 | 0.0346 (7) | 0.0252 (7) | 0.0450 (9) | −0.0036 (6) | 0.0273 (7) | 0.0009 (6) |
C56 | 0.0296 (7) | 0.0258 (7) | 0.0428 (8) | 0.0033 (5) | 0.0235 (7) | 0.0056 (6) |
O3—C3 | 1.2145 (17) | C2—H2A | 0.9900 |
N12—C12 | 1.1466 (19) | C2—H2B | 0.9900 |
C1—C2 | 1.545 (2) | C4—H4A | 0.9900 |
C1—C6 | 1.543 (3) | C4—H4B | 0.9900 |
C1—C11 | 1.536 (3) | C5—H5 | 1.0000 |
C1—C12 | 1.4812 (19) | C6—H6A | 0.9900 |
C2—C3 | 1.507 (2) | C6—H6B | 0.9900 |
C3—C4 | 1.509 (3) | C11—H11A | 0.9800 |
C4—C5 | 1.5450 (19) | C11—H11B | 0.9800 |
C5—C6 | 1.531 (2) | C11—H11C | 0.9800 |
C5—C51 | 1.523 (2) | C15—H15A | 0.9800 |
C15—C54 | 1.507 (3) | C15—H15B | 0.9800 |
C51—C52 | 1.391 (2) | C15—H15C | 0.9800 |
C51—C56 | 1.3917 (18) | C52—H52 | 0.9500 |
C52—C53 | 1.391 (3) | C53—H53 | 0.9500 |
C53—C54 | 1.389 (2) | C55—H55 | 0.9500 |
C54—C55 | 1.393 (2) | C56—H56 | 0.9500 |
C55—C56 | 1.390 (3) | ||
O3···H6Ai | 2.8000 | H4A···C55vii | 2.9200 |
O3···H11Ai | 2.6400 | H4A···C56vii | 2.9500 |
O3···H15Cii | 2.8500 | H4B···C52 | 3.1000 |
O3···H55ii | 2.7700 | H4B···H56i | 2.5700 |
N12···H11Bi | 2.8200 | H5···C12 | 2.5600 |
N12···H5iii | 2.8900 | H5···H52 | 2.3700 |
N12···H6Biv | 2.8700 | H5···N12iii | 2.8900 |
N12···H52iii | 2.7100 | H6A···O3ix | 2.8000 |
C4···C12 | 3.532 (2) | H6A···C56 | 2.7800 |
C12···C4 | 3.532 (2) | H6A···H2B | 2.5900 |
C12···C15v | 3.598 (3) | H6A···H11A | 2.5600 |
C15···C12vi | 3.598 (3) | H6A···H56 | 2.2100 |
C6···H56 | 2.7200 | H6B···C56 | 3.0900 |
C12···H5 | 2.5600 | H6B···H11B | 2.5400 |
C12···H6Biv | 2.9600 | H6B···N12iv | 2.8700 |
C15···H2Bvii | 3.0500 | H6B···C12iv | 2.9600 |
C51···H4Avii | 3.0100 | H11A···O3ix | 2.6400 |
C52···H4B | 3.1000 | H11A···H2B | 2.5000 |
C52···H55i | 3.0600 | H11A···H6A | 2.5600 |
C52···H4Avii | 2.9800 | H11B···N12ix | 2.8200 |
C52···H11Biv | 3.0800 | H11B···H6B | 2.5400 |
C53···H4Avii | 2.9300 | H11B···C52iv | 3.0800 |
C53···H53viii | 2.9700 | H11C···H2A | 2.5600 |
C54···H4Avii | 2.9400 | H15A···H53 | 2.3700 |
C55···H52ix | 3.0600 | H15C···O3x | 2.8500 |
C55···H4Avii | 2.9200 | H15C···H2Bvii | 2.3200 |
C56···H6A | 2.7800 | H15C···H2Avi | 2.5800 |
C56···H6B | 3.0900 | H52···C55i | 3.0600 |
C56···H4Avii | 2.9500 | H52···H5 | 2.3700 |
H2A···H11C | 2.5600 | H52···N12iii | 2.7100 |
H2A···H15Cv | 2.5800 | H53···H15A | 2.3700 |
H2B···H6A | 2.5900 | H53···C53viii | 2.9700 |
H2B···H11A | 2.5000 | H53···H53viii | 2.4800 |
H2B···C15vii | 3.0500 | H55···C52ix | 3.0600 |
H2B···H15Cvii | 2.3200 | H55···O3x | 2.7700 |
H4A···C51vii | 3.0100 | H56···C6 | 2.7200 |
H4A···C52vii | 2.9800 | H56···H4Bix | 2.5700 |
H4A···C53vii | 2.9300 | H56···H6A | 2.2100 |
H4A···C54vii | 2.9400 | ||
C2—C1—C6 | 109.04 (13) | C3—C4—H4B | 109.00 |
C2—C1—C11 | 110.55 (14) | C5—C4—H4A | 109.00 |
C2—C1—C12 | 108.69 (11) | C5—C4—H4B | 109.00 |
C6—C1—C11 | 111.35 (12) | H4A—C4—H4B | 108.00 |
C6—C1—C12 | 108.53 (13) | C4—C5—H5 | 108.00 |
C11—C1—C12 | 108.62 (14) | C6—C5—H5 | 108.00 |
C1—C2—C3 | 112.38 (13) | C51—C5—H5 | 108.00 |
O3—C3—C2 | 121.60 (17) | C1—C6—H6A | 109.00 |
O3—C3—C4 | 122.51 (15) | C1—C6—H6B | 109.00 |
C2—C3—C4 | 115.89 (12) | C5—C6—H6A | 109.00 |
C3—C4—C5 | 112.38 (13) | C5—C6—H6B | 109.00 |
C4—C5—C6 | 110.02 (12) | H6A—C6—H6B | 108.00 |
C4—C5—C51 | 110.09 (12) | C1—C11—H11A | 109.00 |
C6—C5—C51 | 113.81 (11) | C1—C11—H11B | 109.00 |
C1—C6—C5 | 112.03 (11) | C1—C11—H11C | 109.00 |
N12—C12—C1 | 178.70 (18) | H11A—C11—H11B | 109.00 |
C5—C51—C52 | 119.32 (12) | H11A—C11—H11C | 109.00 |
C5—C51—C56 | 122.83 (13) | H11B—C11—H11C | 109.00 |
C52—C51—C56 | 117.83 (15) | C54—C15—H15A | 109.00 |
C51—C52—C53 | 121.07 (12) | C54—C15—H15B | 109.00 |
C52—C53—C54 | 121.23 (14) | C54—C15—H15C | 109.00 |
C15—C54—C53 | 121.54 (16) | H15A—C15—H15B | 109.00 |
C15—C54—C55 | 120.88 (16) | H15A—C15—H15C | 109.00 |
C53—C54—C55 | 117.58 (17) | H15B—C15—H15C | 109.00 |
C54—C55—C56 | 121.31 (13) | C51—C52—H52 | 119.00 |
C51—C56—C55 | 120.95 (14) | C53—C52—H52 | 119.00 |
C1—C2—H2A | 109.00 | C52—C53—H53 | 119.00 |
C1—C2—H2B | 109.00 | C54—C53—H53 | 119.00 |
C3—C2—H2A | 109.00 | C54—C55—H55 | 119.00 |
C3—C2—H2B | 109.00 | C56—C55—H55 | 119.00 |
H2A—C2—H2B | 108.00 | C51—C56—H56 | 120.00 |
C3—C4—H4A | 109.00 | C55—C56—H56 | 120.00 |
C6—C1—C2—C3 | 52.74 (16) | C4—C5—C51—C52 | −88.85 (14) |
C11—C1—C2—C3 | 175.47 (14) | C4—C5—C51—C56 | 89.28 (15) |
C12—C1—C2—C3 | −65.40 (19) | C6—C5—C51—C52 | 147.10 (12) |
C2—C1—C6—C5 | −58.85 (15) | C6—C5—C51—C56 | −34.77 (17) |
C11—C1—C6—C5 | 178.91 (12) | C5—C51—C52—C53 | 178.29 (12) |
C12—C1—C6—C5 | 59.39 (14) | C56—C51—C52—C53 | 0.1 (2) |
C1—C2—C3—O3 | 130.73 (15) | C5—C51—C56—C55 | −179.06 (13) |
C1—C2—C3—C4 | −49.13 (17) | C52—C51—C56—C55 | −0.9 (2) |
O3—C3—C4—C5 | −131.91 (13) | C51—C52—C53—C54 | 1.5 (2) |
C2—C3—C4—C5 | 47.96 (15) | C52—C53—C54—C15 | 176.87 (13) |
C3—C4—C5—C6 | −51.08 (14) | C52—C53—C54—C55 | −2.2 (2) |
C3—C4—C5—C51 | −177.30 (10) | C15—C54—C55—C56 | −177.71 (14) |
C4—C5—C6—C1 | 58.21 (15) | C53—C54—C55—C56 | 1.3 (2) |
C51—C5—C6—C1 | −177.70 (11) | C54—C55—C56—C51 | 0.2 (2) |
Symmetry codes: (i) x, y−1, z; (ii) −x, y−1, −z+1/2; (iii) −x, −y+1, −z+1; (iv) −x, −y+2, −z+1; (v) x−1/2, y−1/2, z; (vi) x+1/2, y+1/2, z; (vii) −x, y, −z+1/2; (viii) −x+1/2, −y+3/2, −z+1; (ix) x, y+1, z; (x) −x, y+1, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4A···Cgvii | 0.99 | 2.61 | 3.5425 (15) | 157 |
Symmetry code: (vii) −x, y, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C15H17NO |
Mr | 227.30 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 160 |
a, b, c (Å) | 23.4475 (5), 6.0370 (1), 21.0740 (5) |
β (°) | 123.267 (1) |
V (Å3) | 2494.22 (9) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.25 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Nonius KappaCCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 37687, 3640, 2682 |
Rint | 0.054 |
(sin θ/λ)max (Å−1) | 0.705 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.170, 1.08 |
No. of reflections | 3640 |
No. of parameters | 154 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.42, −0.27 |
Computer programs: COLLECT (Nonius, 2000), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4A···Cgi | 0.99 | 2.61 | 3.5425 (15) | 157 |
Symmetry code: (i) −x, y, −z+1/2. |
Acknowledgements
AT thanks the UGC, India, for the award of a Minor Research Project [File No. MRP-2355/06(UGC-SERO), Link No. 2355, 10/01/2007].
References
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Subramanyam, M., Thiruvalluvar, A., Sabapathy Mohan, R. T. & Kamatchi, S. (2007). Acta Cryst. E63, o2715–o2716. Web of Science CSD CrossRef IUCr Journals Google Scholar
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The title compound has been analysed as part of our crystallographic studies on substituted cyclohexanes (Subramanyam et al., 2007). Its molecular structure, with atomic numbering scheme, is shown in Fig. 1. The cyclohexane ring adopts a chair conformation. The cyano group and the methyl group at position 1 have axial and equatorial orientations respectively. The benzene ring at position 5 has an equatorial orientation. A C4—H4A···π(-x, y, 1/2 - z) interaction involving the benzene ring is found in the structure. No classical hydrogen bonds are found in the crystal structure.