Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807020399/at2280sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807020399/at2280Isup2.hkl |
CCDC reference: 647706
Key indicators
- Single-crystal X-ray study
- T = 160 K
- Mean (C-C) = 0.002 Å
- R factor = 0.056
- wR factor = 0.163
- Data-to-parameter ratio = 17.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT128_ALERT_4_C Non-standard setting of Space group P21/c .... P21/a PLAT230_ALERT_2_C Hirshfeld Test Diff for C3 - C311 .. 6.48 su
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
A mixture of 3-methyl-5-m-nitrophenylcyclohex-2-enone (4.62 g, 0.02 mol), potassium cyanide (2.6 g, 0.04 mol), ammonium chloride (1.59 g, 0.03 mol), dimethyl formamide (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 column chromatography (hexane-EtOAc, 4.5:1 v/v). The yield of the isolated product was 3.87 g (75%).
H atoms were positioned geometrically and allowed to ride on their parent atoms, with C–H = 0.95–0.99 Å and Uiso=1.2 or 1.5 times Ueq(C).
Related literature were reported by Nagata et al., 1961 and Pandey et al., 2004.
The present X-ray diffraction study was undertaken to determine how the conformation of the system is affected by the substitution of a cyano and methyl groups at position 3 and m-nitrophenyl ring at position 5 of the cyclohexanone. The molecular structure of (I), 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 3 have an axial and equatorial orientations respectively. The phenyl ring at position 5 has an equatorial orientation. The mean plane of atoms C2/C3/C5/C6 and phenyl ring make dihedral angle of 75.97 (6)°. The attached m-nitro group make a 2.4 (3)° tilt with the phenyl ring. In the crystal structure the molecules are stabilized by intermolecular C2–H2B···N311 hydogen bonds (Fig. 2).
For related literature, see: Nagata et al. (1961); Pandey et al. (2004).
Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).
C14H14N2O3 | F(000) = 544 |
Mr = 258.27 | Dx = 1.319 Mg m−3 |
Monoclinic, P21/a | Melting point: 387 K |
Hall symbol: -P 2 y a b | Mo Kα radiation, λ = 0.71073 Å |
a = 12.2284 (3) Å | Cell parameters from 3165 reflections |
b = 8.0986 (3) Å | θ = 2–27.5° |
c = 13.1376 (4) Å | µ = 0.09 mm−1 |
β = 91.336 (2)° | T = 160 K |
V = 1300.70 (7) Å3 | Plate, orange |
Z = 4 | 0.25 × 0.2 × 0.13 mm |
Nonius KappaCCD area-detector diffractometer | 2055 reflections with I > 2σ(I) |
Radiation source: Nonius FR590 sealed tube generator | Rint = 0.097 |
Horizontally mounted graphite crystal monochromator | θmax = 27.5°, θmin = 3.0° |
Detector resolution: 9 pixels mm-1 | h = −15→15 |
φ and ω scans with κ offsets | k = −10→10 |
32792 measured reflections | l = −17→17 |
2968 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.056 | H-atom parameters constrained |
wR(F2) = 0.163 | w = 1/[σ2(Fo2) + (0.0927P)2 + 0.0906P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
2968 reflections | Δρmax = 0.35 e Å−3 |
174 parameters | Δρmin = −0.29 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.060 (7) |
C14H14N2O3 | V = 1300.70 (7) Å3 |
Mr = 258.27 | Z = 4 |
Monoclinic, P21/a | Mo Kα radiation |
a = 12.2284 (3) Å | µ = 0.09 mm−1 |
b = 8.0986 (3) Å | T = 160 K |
c = 13.1376 (4) Å | 0.25 × 0.2 × 0.13 mm |
β = 91.336 (2)° |
Nonius KappaCCD area-detector diffractometer | 2055 reflections with I > 2σ(I) |
32792 measured reflections | Rint = 0.097 |
2968 independent reflections |
R[F2 > 2σ(F2)] = 0.056 | 0 restraints |
wR(F2) = 0.163 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.35 e Å−3 |
2968 reflections | Δρmin = −0.29 e Å−3 |
174 parameters |
Experimental. Solvent used: Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.485 (2) Frames collected: 341 Seconds exposure per frame: 30 Degrees rotation per frame: 2.0 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 | ||
O1 | 0.12273 (10) | 0.92625 (17) | 0.54801 (9) | 0.0339 (4) | |
O53A | 0.24351 (12) | 1.0799 (2) | −0.04547 (11) | 0.0502 (6) | |
O53B | 0.14631 (12) | 1.2738 (2) | −0.11608 (11) | 0.0540 (6) | |
N53 | 0.16554 (13) | 1.1753 (2) | −0.04660 (12) | 0.0376 (6) | |
N311 | −0.09375 (13) | 0.5722 (2) | 0.38559 (16) | 0.0515 (7) | |
C1 | 0.13526 (12) | 0.8854 (2) | 0.45983 (13) | 0.0249 (5) | |
C2 | 0.16985 (13) | 0.7131 (2) | 0.43218 (13) | 0.0256 (5) | |
C3 | 0.10791 (12) | 0.6410 (2) | 0.33822 (13) | 0.0239 (5) | |
C4 | 0.10443 (13) | 0.7681 (2) | 0.25184 (13) | 0.0243 (5) | |
C5 | 0.05352 (12) | 0.9313 (2) | 0.28443 (12) | 0.0217 (5) | |
C6 | 0.12067 (13) | 1.0061 (2) | 0.37311 (13) | 0.0250 (5) | |
C31 | 0.16269 (16) | 0.4811 (2) | 0.30333 (16) | 0.0358 (6) | |
C51 | 0.03902 (13) | 1.0541 (2) | 0.19846 (12) | 0.0229 (5) | |
C52 | 0.10960 (13) | 1.0585 (2) | 0.11632 (13) | 0.0249 (5) | |
C53 | 0.09084 (14) | 1.1732 (2) | 0.03957 (13) | 0.0279 (5) | |
C54 | 0.00549 (15) | 1.2825 (2) | 0.03984 (14) | 0.0332 (6) | |
C55 | −0.06329 (15) | 1.2804 (2) | 0.12226 (15) | 0.0349 (6) | |
C56 | −0.04613 (14) | 1.1673 (2) | 0.20033 (14) | 0.0295 (6) | |
C311 | −0.00532 (14) | 0.6019 (2) | 0.36614 (15) | 0.0317 (6) | |
H2A | 0.24915 | 0.71362 | 0.41861 | 0.0307* | |
H2B | 0.15819 | 0.63968 | 0.49119 | 0.0307* | |
H4A | 0.06158 | 0.72249 | 0.19347 | 0.0291* | |
H4B | 0.17978 | 0.78864 | 0.22894 | 0.0291* | |
H5 | −0.02087 | 0.90594 | 0.31033 | 0.0260* | |
H6A | 0.08331 | 1.10626 | 0.39788 | 0.0299* | |
H6B | 0.19339 | 1.03937 | 0.34867 | 0.0299* | |
H31A | 0.12151 | 0.43534 | 0.24499 | 0.0537* | |
H31B | 0.23782 | 0.50483 | 0.28344 | 0.0537* | |
H31C | 0.16376 | 0.40101 | 0.35925 | 0.0537* | |
H52 | 0.16946 | 0.98404 | 0.11315 | 0.0298* | |
H54 | −0.00627 | 1.35768 | −0.01485 | 0.0398* | |
H55 | −0.12224 | 1.35656 | 0.12528 | 0.0419* | |
H56 | −0.09380 | 1.16735 | 0.25641 | 0.0353* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0349 (7) | 0.0451 (9) | 0.0217 (7) | −0.0008 (6) | −0.0007 (5) | −0.0026 (6) |
O53A | 0.0420 (8) | 0.0731 (12) | 0.0360 (9) | 0.0045 (8) | 0.0105 (6) | 0.0136 (8) |
O53B | 0.0546 (9) | 0.0728 (12) | 0.0347 (9) | −0.0096 (8) | 0.0010 (7) | 0.0312 (8) |
N53 | 0.0368 (9) | 0.0501 (11) | 0.0257 (9) | −0.0121 (8) | −0.0013 (7) | 0.0094 (8) |
N311 | 0.0284 (9) | 0.0470 (12) | 0.0791 (14) | −0.0042 (8) | 0.0007 (8) | 0.0296 (10) |
C1 | 0.0182 (8) | 0.0315 (10) | 0.0249 (10) | −0.0048 (7) | −0.0028 (6) | 0.0012 (8) |
C2 | 0.0257 (9) | 0.0268 (10) | 0.0241 (9) | 0.0003 (7) | −0.0023 (7) | 0.0063 (7) |
C3 | 0.0203 (8) | 0.0224 (9) | 0.0290 (10) | −0.0018 (7) | −0.0007 (7) | 0.0043 (7) |
C4 | 0.0248 (9) | 0.0248 (10) | 0.0232 (9) | −0.0004 (7) | −0.0002 (7) | 0.0025 (7) |
C5 | 0.0193 (8) | 0.0225 (9) | 0.0234 (9) | −0.0009 (6) | 0.0026 (6) | 0.0036 (7) |
C6 | 0.0270 (9) | 0.0227 (10) | 0.0252 (9) | −0.0017 (7) | 0.0006 (7) | 0.0011 (7) |
C31 | 0.0365 (10) | 0.0266 (10) | 0.0440 (12) | 0.0046 (8) | −0.0059 (8) | −0.0010 (9) |
C51 | 0.0234 (8) | 0.0226 (9) | 0.0226 (9) | −0.0039 (7) | −0.0030 (7) | 0.0025 (7) |
C52 | 0.0231 (9) | 0.0265 (10) | 0.0249 (9) | −0.0041 (7) | −0.0021 (7) | 0.0039 (7) |
C53 | 0.0309 (9) | 0.0309 (10) | 0.0218 (9) | −0.0104 (8) | −0.0029 (7) | 0.0046 (8) |
C54 | 0.0417 (11) | 0.0281 (10) | 0.0292 (10) | −0.0055 (8) | −0.0092 (8) | 0.0065 (8) |
C55 | 0.0374 (10) | 0.0306 (11) | 0.0365 (11) | 0.0061 (8) | −0.0058 (8) | 0.0057 (8) |
C56 | 0.0279 (9) | 0.0299 (10) | 0.0306 (10) | 0.0012 (8) | 0.0014 (7) | 0.0022 (8) |
C311 | 0.0275 (10) | 0.0263 (10) | 0.0410 (11) | −0.0012 (8) | −0.0049 (8) | 0.0112 (8) |
O1—C1 | 1.218 (2) | C53—C54 | 1.369 (2) |
O53A—N53 | 1.227 (2) | C54—C55 | 1.387 (3) |
O53B—N53 | 1.231 (2) | C55—C56 | 1.387 (3) |
N53—C53 | 1.471 (2) | C2—H2A | 0.9900 |
N311—C311 | 1.143 (2) | C2—H2B | 0.9900 |
C1—C2 | 1.505 (2) | C4—H4A | 0.9900 |
C1—C6 | 1.509 (2) | C4—H4B | 0.9900 |
C2—C3 | 1.548 (2) | C5—H5 | 1.0000 |
C3—C4 | 1.532 (2) | C6—H6A | 0.9900 |
C3—C31 | 1.533 (2) | C6—H6B | 0.9900 |
C3—C311 | 1.475 (2) | C31—H31A | 0.9800 |
C4—C5 | 1.527 (2) | C31—H31B | 0.9800 |
C5—C6 | 1.534 (2) | C31—H31C | 0.9800 |
C5—C51 | 1.512 (2) | C52—H52 | 0.9500 |
C51—C52 | 1.398 (2) | C54—H54 | 0.9500 |
C51—C56 | 1.388 (2) | C55—H55 | 0.9500 |
C52—C53 | 1.386 (2) | C56—H56 | 0.9500 |
O1···C31i | 3.265 (2) | H4A···C52 | 2.9700 |
O1···C5ii | 3.323 (2) | H4A···H31A | 2.5300 |
O1···C6ii | 3.221 (2) | H4A···O53Bv | 2.7200 |
O53A···C55iii | 3.387 (2) | H4A···H54v | 2.5100 |
O1···H2Ai | 2.8300 | H4B···C52 | 2.7600 |
O1···H31Bi | 2.8400 | H4B···H6B | 2.5700 |
O1···H5ii | 2.6400 | H4B···H31B | 2.5100 |
O1···H6Aii | 2.6500 | H4B···H52 | 2.2000 |
O1···H56ii | 2.7100 | H4B···O53Bxiii | 2.6200 |
O1···H31Ci | 2.8600 | H5···C311 | 2.5700 |
O53A···H52 | 2.4200 | H5···H56 | 2.4000 |
O53A···H55iii | 2.8000 | H5···O1ii | 2.6400 |
O53B···H54 | 2.4100 | H6A···C56 | 3.0500 |
O53B···H4Biv | 2.6200 | H6A···O1ii | 2.6500 |
O53B···H52iv | 2.8200 | H6B···H4B | 2.5700 |
O53B···H4Av | 2.7200 | H6B···N311viii | 2.7900 |
N311···C2vi | 3.441 (2) | H31A···C55xiv | 3.0200 |
N311···H2Bvii | 2.5000 | H31A···C56xiv | 3.0300 |
N311···H2Avi | 2.6300 | H31A···H4A | 2.5300 |
N311···H6Bvi | 2.7900 | H31B···H2A | 2.4500 |
C2···N311viii | 3.441 (2) | H31B···H4B | 2.5100 |
C5···O1ii | 3.323 (2) | H31B···O1ix | 2.8400 |
C6···O1ii | 3.221 (2) | H31B···H56viii | 2.5200 |
C31···O1ix | 3.265 (2) | H31C···H2B | 2.6000 |
C55···O53Ax | 3.387 (2) | H31C···O1ix | 2.8600 |
C4···H52 | 2.6600 | H52···O53A | 2.4200 |
C52···H4A | 2.9700 | H52···C4 | 2.6600 |
C52···H4B | 2.7600 | H52···H4B | 2.2000 |
C54···H54xi | 2.9300 | H52···O53Bxiii | 2.8200 |
C55···H31Axii | 3.0200 | H54···O53B | 2.4100 |
C56···H6A | 3.0500 | H54···C54xi | 2.9300 |
C56···H31Axii | 3.0300 | H54···H4Av | 2.5100 |
C311···H5 | 2.5700 | H54···H54xi | 2.3400 |
H2A···H31B | 2.4500 | H55···O53Ax | 2.8000 |
H2A···O1ix | 2.8300 | H56···H5 | 2.4000 |
H2A···N311viii | 2.6300 | H56···O1ii | 2.7100 |
H2B···H31C | 2.6000 | H56···H31Bvi | 2.5200 |
H2B···N311vii | 2.5000 | ||
O53A—N53—O53B | 123.51 (16) | C3—C2—H2B | 109.00 |
O53A—N53—C53 | 118.66 (15) | H2A—C2—H2B | 108.00 |
O53B—N53—C53 | 117.83 (15) | C3—C4—H4B | 109.00 |
O1—C1—C2 | 121.58 (15) | C3—C4—H4A | 109.00 |
O1—C1—C6 | 121.81 (15) | H4A—C4—H4B | 108.00 |
C2—C1—C6 | 116.58 (14) | C5—C4—H4A | 109.00 |
C1—C2—C3 | 114.03 (13) | C5—C4—H4B | 109.00 |
C2—C3—C4 | 110.00 (13) | C51—C5—H5 | 107.00 |
C2—C3—C31 | 110.37 (13) | C4—C5—H5 | 107.00 |
C2—C3—C311 | 109.12 (14) | C6—C5—H5 | 107.00 |
C4—C3—C31 | 110.54 (14) | C1—C6—H6B | 109.00 |
C4—C3—C311 | 108.57 (13) | C1—C6—H6A | 109.00 |
C31—C3—C311 | 108.20 (14) | H6A—C6—H6B | 108.00 |
C3—C4—C5 | 112.24 (14) | C5—C6—H6A | 109.00 |
C4—C5—C6 | 109.90 (13) | C5—C6—H6B | 109.00 |
C4—C5—C51 | 113.67 (13) | H31A—C31—H31B | 109.00 |
C6—C5—C51 | 111.03 (13) | C3—C31—H31A | 109.00 |
C1—C6—C5 | 111.68 (13) | C3—C31—H31B | 109.00 |
C5—C51—C52 | 121.98 (14) | C3—C31—H31C | 109.00 |
C5—C51—C56 | 119.74 (14) | H31A—C31—H31C | 109.00 |
C52—C51—C56 | 118.28 (15) | H31B—C31—H31C | 109.00 |
C51—C52—C53 | 118.94 (15) | C51—C52—H52 | 121.00 |
N53—C53—C52 | 118.18 (15) | C53—C52—H52 | 121.00 |
N53—C53—C54 | 118.80 (15) | C55—C54—H54 | 121.00 |
C52—C53—C54 | 123.01 (16) | C53—C54—H54 | 121.00 |
C53—C54—C55 | 118.07 (16) | C56—C55—H55 | 120.00 |
C54—C55—C56 | 120.09 (16) | C54—C55—H55 | 120.00 |
C51—C56—C55 | 121.57 (16) | C51—C56—H56 | 119.00 |
C3—C2—H2A | 109.00 | C55—C56—H56 | 119.00 |
C1—C2—H2A | 109.00 | N311—C311—C3 | 178.5 (2) |
C1—C2—H2B | 109.00 | ||
O53A—N53—C53—C52 | −2.6 (2) | C4—C5—C6—C1 | −53.75 (17) |
O53A—N53—C53—C54 | 178.27 (17) | C51—C5—C6—C1 | 179.64 (13) |
O53B—N53—C53—C52 | 177.67 (16) | C4—C5—C51—C52 | −30.4 (2) |
O53B—N53—C53—C54 | −1.5 (2) | C4—C5—C51—C56 | 150.01 (15) |
O1—C1—C2—C3 | 137.96 (15) | C6—C5—C51—C52 | 94.13 (18) |
C6—C1—C2—C3 | −44.03 (19) | C6—C5—C51—C56 | −85.48 (18) |
O1—C1—C6—C5 | −134.95 (15) | C5—C51—C52—C53 | 179.33 (15) |
C2—C1—C6—C5 | 47.06 (18) | C56—C51—C52—C53 | −1.1 (2) |
C1—C2—C3—C4 | 46.89 (18) | C5—C51—C56—C55 | −179.03 (15) |
C1—C2—C3—C31 | 169.12 (14) | C52—C51—C56—C55 | 1.4 (3) |
C1—C2—C3—C311 | −72.11 (17) | C51—C52—C53—N53 | −179.61 (15) |
C2—C3—C4—C5 | −56.14 (16) | C51—C52—C53—C54 | −0.5 (3) |
C31—C3—C4—C5 | −178.28 (13) | N53—C53—C54—C55 | −179.16 (15) |
C311—C3—C4—C5 | 63.19 (17) | C52—C53—C54—C55 | 1.7 (3) |
C3—C4—C5—C6 | 60.31 (17) | C53—C54—C55—C56 | −1.4 (3) |
C3—C4—C5—C51 | −174.57 (13) | C54—C55—C56—C51 | −0.1 (3) |
Symmetry codes: (i) −x+1/2, y+1/2, −z+1; (ii) −x, −y+2, −z+1; (iii) x+1/2, −y+5/2, z; (iv) −x+1/2, y+1/2, −z; (v) −x, −y+2, −z; (vi) x−1/2, −y+3/2, z; (vii) −x, −y+1, −z+1; (viii) x+1/2, −y+3/2, z; (ix) −x+1/2, y−1/2, −z+1; (x) x−1/2, −y+5/2, z; (xi) −x, −y+3, −z; (xii) x, y+1, z; (xiii) −x+1/2, y−1/2, −z; (xiv) x, y−1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2B···N311vii | 0.99 | 2.50 | 3.470 (2) | 167 |
Symmetry code: (vii) −x, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C14H14N2O3 |
Mr | 258.27 |
Crystal system, space group | Monoclinic, P21/a |
Temperature (K) | 160 |
a, b, c (Å) | 12.2284 (3), 8.0986 (3), 13.1376 (4) |
β (°) | 91.336 (2) |
V (Å3) | 1300.70 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.25 × 0.2 × 0.13 |
Data collection | |
Diffractometer | Nonius KappaCCD area-detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 32792, 2968, 2055 |
Rint | 0.097 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.163, 1.05 |
No. of reflections | 2968 |
No. of parameters | 174 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.35, −0.29 |
Computer programs: COLLECT (Nonius, 2000), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2B···N311i | 0.99 | 2.50 | 3.470 (2) | 167 |
Symmetry code: (i) −x, −y+1, −z+1. |
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Related literature were reported by Nagata et al., 1961 and Pandey et al., 2004.
The present X-ray diffraction study was undertaken to determine how the conformation of the system is affected by the substitution of a cyano and methyl groups at position 3 and m-nitrophenyl ring at position 5 of the cyclohexanone. The molecular structure of (I), 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 3 have an axial and equatorial orientations respectively. The phenyl ring at position 5 has an equatorial orientation. The mean plane of atoms C2/C3/C5/C6 and phenyl ring make dihedral angle of 75.97 (6)°. The attached m-nitro group make a 2.4 (3)° tilt with the phenyl ring. In the crystal structure the molecules are stabilized by intermolecular C2–H2B···N311 hydogen bonds (Fig. 2).