organic compounds
rac-5-Acetyl-6-hydroxy-3,6-dimethyl-4-phenyl-4,5,6,7-tetrahydro-2H-indazole
aBaku State University, Z. Khalilov St 23, Baku, AZ-1148, Azerbaijan
*Correspondence e-mail: orglab@mail.ru
The title compound, C17H20N2O2, is chiral but crystallizes in a centrosymmetric as a racemate, the at the stereogenic centres being 2S*,3R*,4S*. The cyclohexane ring adopts a half-chair conformation while the pyrazole ring has an The crystal packing displays intermolecular O—H⋯N and N—H⋯O hydrogen bonding.
Related literature
For background to the use of β-cycloketols as synthons in syntheses of pyrazoles, see: Pramula et al. (1985).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2005); cell SAINT-Plus, (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.
Supporting information
10.1107/S1600536811013195/kp2321sup1.cif
contains datablocks Global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536811013195/kp2321Isup2.hkl
2,4-Diacetyl-5-hydroxy-5-metyl-3-phenilcyclohexanon (20 mmol), hydrazine hydrate (20 mmol) were dissolved in 20 mL ethanol. The mixture was stirred at 345–350 K for 10 h. After cooling to room temperature, white crystals were obtained. The crystals were filtered off and washed with ethanol. Then, they were dissolved in ethanol (50 mL) and recrystallised to yield colourless block-shaped crystals suitable for data collection.
The hydrogen atoms of the NH and OH-groups of the molecule were located in a difference-Fourier map and included in the
with fixed positional and isotropic displacement parameters [Uiso(H) = 1.5Ueq(C) for CH3-group and Uiso(H) = 1.2Ueq(N) for amino groups]. The other hydrogen atoms were placed in calculated positions and refined in the riding model with the fixed isotropic displacement parameters [Uiso(H) = 1.2Ueq(C)].Data collection: APEX2 (Bruker, 2005); cell
SAINT-Plus, (Bruker, 2001); data reduction: SAINT-Plus, (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).C17H20N2O2 | F(000) = 1216 |
Mr = 284.35 | Dx = 1.261 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 6277 reflections |
a = 18.6999 (9) Å | θ = 2.5–28.2° |
b = 5.6415 (3) Å | µ = 0.08 mm−1 |
c = 28.4855 (14) Å | T = 296 K |
β = 94.498 (1)° | Prism, colorless |
V = 2995.8 (3) Å3 | 0.30 × 0.30 × 0.20 mm |
Z = 8 |
Bruker APEXII CCD area-detector diffractometer | 3709 independent reflections |
Radiation source: fine-focus sealed tube | 3079 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
phi and ω scans | θmax = 28.3°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −24→24 |
Tmin = 0.975, Tmax = 0.984 | k = −7→7 |
16597 measured reflections | l = −38→37 |
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)] = 0.045 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.129 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0701P)2 + 1.7992P] where P = (Fo2 + 2Fc2)/3 |
3709 reflections | (Δ/σ)max = 0.001 |
193 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
C17H20N2O2 | V = 2995.8 (3) Å3 |
Mr = 284.35 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 18.6999 (9) Å | µ = 0.08 mm−1 |
b = 5.6415 (3) Å | T = 296 K |
c = 28.4855 (14) Å | 0.30 × 0.30 × 0.20 mm |
β = 94.498 (1)° |
Bruker APEXII CCD area-detector diffractometer | 3709 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | 3079 reflections with I > 2σ(I) |
Tmin = 0.975, Tmax = 0.984 | Rint = 0.021 |
16597 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.129 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.32 e Å−3 |
3709 reflections | Δρmin = −0.16 e Å−3 |
193 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.76048 (5) | 0.7902 (2) | 0.61991 (4) | 0.0481 (3) | |
O2 | 0.62374 (5) | 0.43848 (16) | 0.52715 (3) | 0.0372 (2) | |
H2A | 0.6097 | 0.4443 | 0.4992 | 0.056* | |
N1 | 0.42526 (6) | 0.5528 (2) | 0.57008 (4) | 0.0369 (3) | |
N2 | 0.41169 (6) | 0.3900 (2) | 0.60311 (4) | 0.0390 (3) | |
H2C | 0.3693 | 0.3393 | 0.6074 | 0.047* | |
C1 | 0.47121 (7) | 0.3149 (3) | 0.62867 (5) | 0.0347 (3) | |
C1A | 0.52770 (6) | 0.4380 (2) | 0.61152 (4) | 0.0291 (3) | |
C2 | 0.60733 (6) | 0.4279 (2) | 0.62496 (4) | 0.0273 (2) | |
H2B | 0.6259 | 0.2787 | 0.6132 | 0.033* | |
C3 | 0.64412 (6) | 0.6363 (2) | 0.60052 (4) | 0.0266 (2) | |
H3A | 0.6312 | 0.7817 | 0.6167 | 0.032* | |
C4 | 0.61636 (6) | 0.6655 (2) | 0.54788 (4) | 0.0284 (2) | |
C5 | 0.53694 (7) | 0.7403 (2) | 0.54570 (5) | 0.0335 (3) | |
H5A | 0.5334 | 0.9023 | 0.5567 | 0.040* | |
H5B | 0.5164 | 0.7336 | 0.5134 | 0.040* | |
C5A | 0.49626 (6) | 0.5808 (2) | 0.57540 (4) | 0.0313 (3) | |
C6 | 0.46830 (8) | 0.1288 (3) | 0.66523 (6) | 0.0514 (4) | |
H6A | 0.4196 | 0.1082 | 0.6729 | 0.077* | |
H6B | 0.4975 | 0.1754 | 0.6929 | 0.077* | |
H6C | 0.4859 | −0.0178 | 0.6535 | 0.077* | |
C7 | 0.62509 (6) | 0.4376 (2) | 0.67804 (4) | 0.0309 (3) | |
C8 | 0.59834 (10) | 0.6182 (3) | 0.70426 (5) | 0.0516 (4) | |
H8A | 0.5690 | 0.7324 | 0.6892 | 0.062* | |
C9 | 0.61420 (11) | 0.6334 (4) | 0.75247 (6) | 0.0605 (5) | |
H9A | 0.5956 | 0.7568 | 0.7694 | 0.073* | |
C10 | 0.65747 (10) | 0.4662 (4) | 0.77516 (5) | 0.0561 (4) | |
H10A | 0.6686 | 0.4763 | 0.8075 | 0.067* | |
C11 | 0.68412 (9) | 0.2846 (4) | 0.74998 (6) | 0.0565 (4) | |
H11A | 0.7131 | 0.1701 | 0.7653 | 0.068* | |
C12 | 0.66811 (8) | 0.2700 (3) | 0.70155 (5) | 0.0422 (3) | |
H12A | 0.6866 | 0.1457 | 0.6848 | 0.051* | |
C13 | 0.72575 (6) | 0.6185 (2) | 0.60593 (4) | 0.0324 (3) | |
C14 | 0.76231 (8) | 0.3969 (3) | 0.59270 (7) | 0.0492 (4) | |
H14A | 0.8133 | 0.4200 | 0.5960 | 0.074* | |
H14B | 0.7476 | 0.3575 | 0.5606 | 0.074* | |
H14C | 0.7496 | 0.2701 | 0.6129 | 0.074* | |
C15 | 0.65806 (8) | 0.8528 (3) | 0.52295 (5) | 0.0392 (3) | |
H15A | 0.6384 | 0.8680 | 0.4909 | 0.059* | |
H15B | 0.7075 | 0.8065 | 0.5234 | 0.059* | |
H15C | 0.6546 | 1.0021 | 0.5388 | 0.059* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0303 (5) | 0.0525 (6) | 0.0605 (7) | −0.0132 (4) | −0.0030 (4) | −0.0091 (5) |
O2 | 0.0473 (5) | 0.0326 (5) | 0.0306 (4) | 0.0027 (4) | −0.0034 (4) | −0.0043 (4) |
N1 | 0.0252 (5) | 0.0509 (7) | 0.0342 (5) | −0.0004 (5) | −0.0011 (4) | 0.0027 (5) |
N2 | 0.0234 (5) | 0.0517 (7) | 0.0418 (6) | −0.0053 (5) | 0.0024 (4) | 0.0039 (5) |
C1 | 0.0266 (6) | 0.0406 (7) | 0.0372 (6) | −0.0024 (5) | 0.0034 (5) | 0.0025 (5) |
C1A | 0.0241 (5) | 0.0327 (6) | 0.0301 (6) | −0.0016 (4) | 0.0005 (4) | 0.0015 (5) |
C2 | 0.0237 (5) | 0.0292 (6) | 0.0286 (5) | 0.0000 (4) | −0.0005 (4) | 0.0015 (4) |
C3 | 0.0220 (5) | 0.0275 (5) | 0.0299 (5) | −0.0015 (4) | 0.0004 (4) | −0.0016 (4) |
C4 | 0.0277 (5) | 0.0289 (6) | 0.0284 (5) | −0.0011 (4) | 0.0008 (4) | 0.0005 (4) |
C5 | 0.0293 (6) | 0.0365 (6) | 0.0338 (6) | 0.0014 (5) | −0.0019 (5) | 0.0066 (5) |
C5A | 0.0256 (6) | 0.0375 (6) | 0.0302 (6) | −0.0003 (5) | −0.0009 (4) | 0.0005 (5) |
C6 | 0.0388 (8) | 0.0555 (9) | 0.0611 (10) | −0.0003 (7) | 0.0110 (7) | 0.0223 (8) |
C7 | 0.0254 (5) | 0.0364 (6) | 0.0305 (6) | −0.0010 (5) | −0.0006 (4) | 0.0036 (5) |
C8 | 0.0628 (10) | 0.0550 (9) | 0.0363 (7) | 0.0217 (8) | −0.0006 (7) | −0.0010 (7) |
C9 | 0.0754 (12) | 0.0694 (12) | 0.0368 (8) | 0.0071 (10) | 0.0062 (8) | −0.0096 (8) |
C10 | 0.0557 (9) | 0.0811 (13) | 0.0306 (7) | −0.0116 (9) | −0.0017 (6) | 0.0079 (8) |
C11 | 0.0501 (9) | 0.0747 (12) | 0.0429 (8) | 0.0074 (8) | −0.0067 (7) | 0.0210 (8) |
C12 | 0.0390 (7) | 0.0463 (8) | 0.0406 (7) | 0.0067 (6) | 0.0000 (6) | 0.0088 (6) |
C13 | 0.0245 (5) | 0.0397 (7) | 0.0326 (6) | −0.0046 (5) | 0.0002 (4) | 0.0021 (5) |
C14 | 0.0283 (6) | 0.0477 (8) | 0.0723 (10) | 0.0031 (6) | 0.0074 (6) | −0.0021 (8) |
C15 | 0.0376 (7) | 0.0406 (7) | 0.0402 (7) | −0.0055 (6) | 0.0076 (5) | 0.0066 (6) |
O1—C13 | 1.2157 (17) | C6—H6A | 0.9600 |
O2—C4 | 1.4215 (15) | C6—H6B | 0.9600 |
O2—H2A | 0.8200 | C6—H6C | 0.9600 |
N1—C5A | 1.3338 (16) | C7—C8 | 1.380 (2) |
N1—N2 | 1.3529 (16) | C7—C12 | 1.3803 (18) |
N2—C1 | 1.3496 (17) | C8—C9 | 1.385 (2) |
N2—H2C | 0.8600 | C8—H8A | 0.9300 |
C1—C1A | 1.3847 (17) | C9—C10 | 1.371 (3) |
C1—C6 | 1.483 (2) | C9—H9A | 0.9300 |
C1A—C5A | 1.3996 (17) | C10—C11 | 1.367 (3) |
C1A—C2 | 1.5093 (16) | C10—H10A | 0.9300 |
C2—C7 | 1.5235 (16) | C11—C12 | 1.391 (2) |
C2—C3 | 1.5543 (16) | C11—H11A | 0.9300 |
C2—H2B | 0.9800 | C12—H12A | 0.9300 |
C3—C13 | 1.5256 (16) | C13—C14 | 1.488 (2) |
C3—C4 | 1.5566 (16) | C14—H14A | 0.9600 |
C3—H3A | 0.9800 | C14—H14B | 0.9600 |
C4—C15 | 1.5218 (17) | C14—H14C | 0.9600 |
C4—C5 | 1.5405 (17) | C15—H15A | 0.9600 |
C5—C5A | 1.4847 (18) | C15—H15B | 0.9600 |
C5—H5A | 0.9700 | C15—H15C | 0.9600 |
C5—H5B | 0.9700 | ||
C4—O2—H2A | 109.5 | C1—C6—H6B | 109.5 |
C5A—N1—N2 | 103.94 (10) | H6A—C6—H6B | 109.5 |
C1—N2—N1 | 113.36 (11) | C1—C6—H6C | 109.5 |
C1—N2—H2C | 123.3 | H6A—C6—H6C | 109.5 |
N1—N2—H2C | 123.3 | H6B—C6—H6C | 109.5 |
N2—C1—C1A | 105.78 (12) | C8—C7—C12 | 117.74 (12) |
N2—C1—C6 | 121.79 (12) | C8—C7—C2 | 120.25 (11) |
C1A—C1—C6 | 132.37 (12) | C12—C7—C2 | 122.01 (12) |
C1—C1A—C5A | 105.07 (11) | C7—C8—C9 | 121.61 (15) |
C1—C1A—C2 | 131.02 (11) | C7—C8—H8A | 119.2 |
C5A—C1A—C2 | 123.88 (11) | C9—C8—H8A | 119.2 |
C1A—C2—C7 | 112.60 (10) | C10—C9—C8 | 119.82 (17) |
C1A—C2—C3 | 108.68 (9) | C10—C9—H9A | 120.1 |
C7—C2—C3 | 110.35 (9) | C8—C9—H9A | 120.1 |
C1A—C2—H2B | 108.4 | C11—C10—C9 | 119.62 (15) |
C7—C2—H2B | 108.4 | C11—C10—H10A | 120.2 |
C3—C2—H2B | 108.4 | C9—C10—H10A | 120.2 |
C13—C3—C2 | 112.29 (10) | C10—C11—C12 | 120.39 (15) |
C13—C3—C4 | 111.09 (9) | C10—C11—H11A | 119.8 |
C2—C3—C4 | 112.68 (9) | C12—C11—H11A | 119.8 |
C13—C3—H3A | 106.8 | C7—C12—C11 | 120.82 (15) |
C2—C3—H3A | 106.8 | C7—C12—H12A | 119.6 |
C4—C3—H3A | 106.8 | C11—C12—H12A | 119.6 |
O2—C4—C15 | 111.21 (10) | O1—C13—C14 | 120.56 (12) |
O2—C4—C5 | 110.78 (10) | O1—C13—C3 | 119.02 (12) |
C15—C4—C5 | 108.59 (10) | C14—C13—C3 | 120.39 (11) |
O2—C4—C3 | 105.60 (9) | C13—C14—H14A | 109.5 |
C15—C4—C3 | 112.25 (10) | C13—C14—H14B | 109.5 |
C5—C4—C3 | 108.38 (9) | H14A—C14—H14B | 109.5 |
C5A—C5—C4 | 110.28 (10) | C13—C14—H14C | 109.5 |
C5A—C5—H5A | 109.6 | H14A—C14—H14C | 109.5 |
C4—C5—H5A | 109.6 | H14B—C14—H14C | 109.5 |
C5A—C5—H5B | 109.6 | C4—C15—H15A | 109.5 |
C4—C5—H5B | 109.6 | C4—C15—H15B | 109.5 |
H5A—C5—H5B | 108.1 | H15A—C15—H15B | 109.5 |
N1—C5A—C1A | 111.85 (11) | C4—C15—H15C | 109.5 |
N1—C5A—C5 | 123.86 (11) | H15A—C15—H15C | 109.5 |
C1A—C5A—C5 | 124.28 (11) | H15B—C15—H15C | 109.5 |
C1—C6—H6A | 109.5 | ||
C5A—N1—N2—C1 | −0.17 (16) | N2—N1—C5A—C1A | −0.17 (15) |
N1—N2—C1—C1A | 0.43 (16) | N2—N1—C5A—C5 | 178.45 (12) |
N1—N2—C1—C6 | −177.22 (13) | C1—C1A—C5A—N1 | 0.43 (15) |
N2—C1—C1A—C5A | −0.50 (15) | C2—C1A—C5A—N1 | 178.64 (11) |
C6—C1—C1A—C5A | 176.80 (16) | C1—C1A—C5A—C5 | −178.19 (12) |
N2—C1—C1A—C2 | −178.53 (13) | C2—C1A—C5A—C5 | 0.0 (2) |
C6—C1—C1A—C2 | −1.2 (3) | C4—C5—C5A—N1 | −158.94 (12) |
C1—C1A—C2—C7 | −47.39 (18) | C4—C5—C5A—C1A | 19.52 (18) |
C5A—C1A—C2—C7 | 134.90 (13) | C1A—C2—C7—C8 | −53.32 (17) |
C1—C1A—C2—C3 | −169.96 (13) | C3—C2—C7—C8 | 68.31 (16) |
C5A—C1A—C2—C3 | 12.33 (16) | C1A—C2—C7—C12 | 127.01 (13) |
C1A—C2—C3—C13 | −171.20 (10) | C3—C2—C7—C12 | −111.37 (13) |
C7—C2—C3—C13 | 64.88 (13) | C12—C7—C8—C9 | 0.5 (3) |
C1A—C2—C3—C4 | −44.84 (13) | C2—C7—C8—C9 | −179.23 (16) |
C7—C2—C3—C4 | −168.76 (9) | C7—C8—C9—C10 | 0.0 (3) |
C13—C3—C4—O2 | 74.30 (12) | C8—C9—C10—C11 | −0.5 (3) |
C2—C3—C4—O2 | −52.70 (12) | C9—C10—C11—C12 | 0.6 (3) |
C13—C3—C4—C15 | −47.03 (14) | C8—C7—C12—C11 | −0.4 (2) |
C2—C3—C4—C15 | −174.04 (10) | C2—C7—C12—C11 | 179.28 (13) |
C13—C3—C4—C5 | −166.96 (10) | C10—C11—C12—C7 | −0.1 (3) |
C2—C3—C4—C5 | 66.04 (12) | C2—C3—C13—O1 | −129.62 (13) |
O2—C4—C5—C5A | 65.66 (13) | C4—C3—C13—O1 | 103.16 (14) |
C15—C4—C5—C5A | −171.94 (11) | C2—C3—C13—C14 | 52.50 (16) |
C3—C4—C5—C5A | −49.75 (13) | C4—C3—C13—C14 | −74.72 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2A···N1i | 0.82 | 2.03 | 2.8487 (14) | 178 |
N2—H2C···O1ii | 0.86 | 2.11 | 2.9587 (15) | 168 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1/2, y−1/2, z. |
Experimental details
Crystal data | |
Chemical formula | C17H20N2O2 |
Mr | 284.35 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 296 |
a, b, c (Å) | 18.6999 (9), 5.6415 (3), 28.4855 (14) |
β (°) | 94.498 (1) |
V (Å3) | 2995.8 (3) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.30 × 0.30 × 0.20 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2003) |
Tmin, Tmax | 0.975, 0.984 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16597, 3709, 3079 |
Rint | 0.021 |
(sin θ/λ)max (Å−1) | 0.668 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.129, 1.00 |
No. of reflections | 3709 |
No. of parameters | 193 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.32, −0.16 |
Computer programs: APEX2 (Bruker, 2005), SAINT-Plus, (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2A···N1i | 0.82 | 2.03 | 2.8487 (14) | 178 |
N2—H2C···O1ii | 0.86 | 2.11 | 2.9587 (15) | 168 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x−1/2, y−1/2, z. |
Acknowledgements
We thank Professor Victor N. Khrustalev for fruitful discussions and help in this work.
References
Bruker (2001). SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Pramula, B., Rajanarender, E., Shoolery, J. N. & Krishna, M. (1985). Ind. J. Chem. Sect. B, 24, 1255–1258. Google Scholar
Sheldrick, G. M. (2003). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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The exploitation of a simple molecule with different functionalities for the synthesis of heterocycles is usefula approach. In fact, the β-cycloketols has been used as an effective synthon in some projected syntheses of pyrazoles (Pramula et al. 1985).
In the title compound, C17H20N2O2 (I), the cyclohexane ring adopts a half-chair conformation (Fig. 1). Cyclohexane ring has a chair conformation. The phenyl ring is in a pseudo-equatorial position. The torsion angle between the acetyl group and the phenyl substituent (C7—C2—C3—C13) is 64.88 (13) °indicating the pseudo-axial location of hydrogen atoms at C2 and C3. The crystal of (I) is racemate and consists of enantiomeric pairs where the relative configuration of the centres are 2S*,3R*,4S*. The crystal structure involves N—H···O and O—H···N intermolecular hydrogen bonds (Table 1 and Fig. 2).