organic compounds
2-[(1S,3S)-3-Acetyl-2,2-dimethylcyclobutyl]-N-(m-tolyl)acetamide
aInstitute of Chemical Industry of Forest Products, Chinese Academy of Forestry, Nanjing 210042, People's Republic of China, and bCollege of Forestry, Jiangxi Agricultural University, Nanchang 330045, People's Republic of China
*Correspondence e-mail: zqsong@public1.ptt.js.cn
The title compound, C17H23NO2, contains two chiral centres and was synthesized from 2-(3-acetyl-2,2-dimethylcyclobutyl)acetic acid and m-toluidine. The cyclobutane ring is not flat but flexed as though folded from the dimethyl-substituted C atom to the unsubstituted C atom, with a dihedral angle of 25.9°. The is stabilized by N—H⋯O and C—H⋯O hydrogen-bonding interactions.
Experimental
Crystal data
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Refinement
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Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
Supporting information
https://doi.org/10.1107/S160053680706641X/at2522sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053680706641X/at2522Isup2.hkl
The title compound was synthesized from m-toluidine and 2-(3-acetyl-2,2-dimethylcyclobutyl) acetyl chloride at room temperature. The acetyl chloride was obtained using 2-(3-acetyl-2,2-dimethylcyclobutyl)acetic acid (pinonic acid), thionyl chloride as raw materials and dichloromethane as solvent. Pinonic acid (27 mmol) and thionyl chloride (32 mmol) were dissolved in dichloromethane (50 ml). The resulting mixture was refluxed for 8 h. After refluxing the solvent was distilled away under vacuum and the remainder was 2-(3-acetyl-2,2-dimethylcyclobutyl)acetyl chloride. The acetyl chloride reacted with m-toluidine (27 mmol) for 24 h using dichloromethane as solvent. After the reaction was complete the solvent was distilled away and the crude title compound was gained. The pure compound was obtained by crystallizing from a mixture of ethanol (40 ml) and water (40 ml). Crystals of the title compound suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution.
All H atoms were placed geometrically, with the C—H distances in the range 0.93–0.98 Å and N—H = 0.86 Å, and included in the
in riding motion approximation with Uiso(H) = 1.2 or 1.5Ueq(H) of the carrier atom.Terpenes are convenient chiral precursors due to their availability and low cost, and among them, a-pinene (both enantiomers) and verbenone are prominent. For instance, pinene has been used as starting material for the production of some compounds of industrial interest (Mitra & Khanra, 1977). Chiral cyclobutane compound, pinonic acid, can be synthesized from a-pinene. Many derivatives of pinonic acid have interesting biological properties. So we synthesized several derivatives of pinonic acid. In our previous paper we have reported the
of 2-[(1S,3S)-3-acetyl-2,2-dimethylcyclobutyl]-N-(2,6-difluorophenyl) acetamide (Yin et al., 2007). Now we synthesized the title compound (I) and report here its crystal structure.The molecular structure of (I) is shown in Fig. 1. A l l bond lengths and angles are normal. The
is stabilized by N—H···O and C—H···O hydrogen bonding interactions (Table 1).For related literature, see: Mitra & Khanra (1977); Yin et al. (2007).
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell
CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).C17H23NO2 | Dx = 1.136 Mg m−3 |
Mr = 273.36 | Melting point: 367 K |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 25 reflections |
a = 12.513 (3) Å | θ = 8–13° |
b = 9.5190 (19) Å | µ = 0.07 mm−1 |
c = 26.844 (5) Å | T = 293 K |
V = 3197.4 (11) Å3 | Quadrate, colourless |
Z = 8 | 0.40 × 0.20 × 0.20 mm |
F(000) = 1184 |
Enraf–Nonius CAD-4 diffractometer | 1385 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.032 |
Graphite monochromator | θmax = 26.0°, θmin = 1.5° |
ω/2θ scans | h = 0→15 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→11 |
Tmin = 0.951, Tmax = 0.975 | l = 0→32 |
3150 measured reflections | 3 standard reflections every 200 reflections |
3120 independent reflections | intensity decay: none |
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)] = 0.073 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.170 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.05P)2] where P = (Fo2 + 2Fc2)/3 |
3120 reflections | (Δ/σ)max < 0.001 |
181 parameters | Δρmax = 0.14 e Å−3 |
0 restraints | Δρmin = −0.14 e Å−3 |
C17H23NO2 | V = 3197.4 (11) Å3 |
Mr = 273.36 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 12.513 (3) Å | µ = 0.07 mm−1 |
b = 9.5190 (19) Å | T = 293 K |
c = 26.844 (5) Å | 0.40 × 0.20 × 0.20 mm |
Enraf–Nonius CAD-4 diffractometer | 1385 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.032 |
Tmin = 0.951, Tmax = 0.975 | 3 standard reflections every 200 reflections |
3150 measured reflections | intensity decay: none |
3120 independent reflections |
R[F2 > 2σ(F2)] = 0.073 | 0 restraints |
wR(F2) = 0.170 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.14 e Å−3 |
3120 reflections | Δρmin = −0.14 e Å−3 |
181 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 | ||
N | 0.7095 (2) | 0.0658 (3) | 0.68825 (10) | 0.0721 (8) | |
H0A | 0.7277 | −0.0171 | 0.6977 | 0.087* | |
O1 | 0.6178 (2) | −0.0407 (3) | 0.92753 (10) | 0.1064 (9) | |
C1 | 0.4701 (3) | 0.1175 (5) | 0.93668 (16) | 0.1272 (16) | |
H1A | 0.4414 | 0.0449 | 0.9576 | 0.191* | |
H1B | 0.4227 | 0.1333 | 0.9091 | 0.191* | |
H1C | 0.4774 | 0.2026 | 0.9556 | 0.191* | |
O2 | 0.7021 (2) | 0.2940 (2) | 0.71316 (9) | 0.0883 (8) | |
C2 | 0.5782 (3) | 0.0728 (4) | 0.91735 (14) | 0.0830 (11) | |
C3 | 0.6333 (3) | 0.1758 (3) | 0.88408 (12) | 0.0684 (9) | |
H3A | 0.6270 | 0.2708 | 0.8978 | 0.082* | |
C4 | 0.5977 (3) | 0.1749 (3) | 0.82785 (11) | 0.0643 (9) | |
C5 | 0.7192 (2) | 0.1983 (3) | 0.81526 (11) | 0.0642 (8) | |
H5A | 0.7331 | 0.2993 | 0.8128 | 0.077* | |
C6 | 0.7475 (3) | 0.1488 (4) | 0.86728 (11) | 0.0777 (10) | |
H6A | 0.7682 | 0.0507 | 0.8688 | 0.093* | |
H6B | 0.7999 | 0.2077 | 0.8838 | 0.093* | |
C7 | 0.5230 (3) | 0.2938 (4) | 0.81276 (14) | 0.1015 (13) | |
H7A | 0.4510 | 0.2698 | 0.8216 | 0.152* | |
H7B | 0.5274 | 0.3081 | 0.7774 | 0.152* | |
H7C | 0.5435 | 0.3784 | 0.8297 | 0.152* | |
C8 | 0.5565 (3) | 0.0333 (3) | 0.81108 (12) | 0.0782 (10) | |
H8A | 0.4824 | 0.0246 | 0.8197 | 0.117* | |
H8B | 0.5966 | −0.0397 | 0.8272 | 0.117* | |
H8C | 0.5645 | 0.0249 | 0.7756 | 0.117* | |
C9 | 0.7689 (3) | 0.1250 (3) | 0.77045 (12) | 0.0771 (10) | |
H9A | 0.8452 | 0.1427 | 0.7705 | 0.092* | |
H9B | 0.7584 | 0.0245 | 0.7738 | 0.092* | |
C10 | 0.7236 (3) | 0.1716 (3) | 0.72154 (12) | 0.0662 (9) | |
C11 | 0.6677 (3) | 0.0789 (3) | 0.63926 (13) | 0.0650 (9) | |
C12 | 0.5888 (3) | 0.1753 (3) | 0.62739 (16) | 0.0855 (11) | |
H12A | 0.5602 | 0.2353 | 0.6513 | 0.103* | |
C13 | 0.5545 (3) | 0.1783 (4) | 0.57870 (19) | 0.1012 (13) | |
H13A | 0.5033 | 0.2443 | 0.5698 | 0.121* | |
C14 | 0.5914 (3) | 0.0904 (4) | 0.54333 (16) | 0.0931 (12) | |
H14A | 0.5657 | 0.0978 | 0.5109 | 0.112* | |
C15 | 0.6686 (3) | −0.0127 (4) | 0.55487 (14) | 0.0801 (10) | |
C16 | 0.7049 (3) | −0.0140 (3) | 0.60417 (13) | 0.0723 (9) | |
H16A | 0.7559 | −0.0800 | 0.6135 | 0.087* | |
C17 | 0.7134 (3) | −0.1128 (5) | 0.51691 (14) | 0.1146 (14) | |
H17A | 0.6788 | −0.0977 | 0.4854 | 0.172* | |
H17B | 0.7011 | −0.2077 | 0.5276 | 0.172* | |
H17C | 0.7888 | −0.0971 | 0.5134 | 0.172* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N | 0.088 (2) | 0.0515 (15) | 0.077 (2) | 0.0067 (14) | 0.0022 (16) | 0.0046 (15) |
O1 | 0.115 (2) | 0.099 (2) | 0.105 (2) | −0.0141 (18) | −0.0003 (17) | 0.0199 (17) |
C1 | 0.085 (3) | 0.175 (4) | 0.122 (4) | −0.020 (3) | 0.026 (3) | −0.006 (3) |
O2 | 0.124 (2) | 0.0526 (14) | 0.0881 (17) | −0.0010 (13) | 0.0038 (15) | 0.0082 (12) |
C2 | 0.102 (3) | 0.079 (2) | 0.068 (2) | −0.015 (2) | −0.003 (2) | −0.007 (2) |
C3 | 0.078 (2) | 0.0583 (18) | 0.069 (2) | −0.0117 (18) | 0.0023 (18) | −0.0043 (17) |
C4 | 0.074 (2) | 0.0616 (19) | 0.057 (2) | −0.0020 (17) | −0.0052 (17) | 0.0061 (16) |
C5 | 0.063 (2) | 0.0605 (19) | 0.070 (2) | −0.0078 (16) | 0.0058 (17) | 0.0026 (17) |
C6 | 0.067 (2) | 0.092 (2) | 0.074 (2) | −0.0174 (18) | −0.0040 (19) | 0.006 (2) |
C7 | 0.097 (3) | 0.098 (3) | 0.110 (3) | 0.025 (2) | 0.002 (2) | 0.015 (2) |
C8 | 0.077 (2) | 0.081 (2) | 0.077 (2) | −0.0201 (19) | −0.0042 (19) | 0.0009 (19) |
C9 | 0.080 (2) | 0.072 (2) | 0.079 (2) | 0.0042 (18) | 0.008 (2) | 0.0053 (19) |
C10 | 0.078 (2) | 0.0522 (19) | 0.069 (2) | 0.0044 (18) | 0.0147 (18) | 0.0129 (19) |
C11 | 0.067 (2) | 0.0499 (18) | 0.079 (2) | −0.0047 (16) | 0.0074 (19) | 0.0102 (19) |
C12 | 0.084 (3) | 0.059 (2) | 0.113 (3) | 0.013 (2) | 0.001 (2) | −0.003 (2) |
C13 | 0.090 (3) | 0.096 (3) | 0.117 (4) | 0.002 (3) | −0.022 (3) | 0.011 (3) |
C14 | 0.088 (3) | 0.090 (3) | 0.101 (3) | −0.015 (2) | −0.025 (2) | 0.014 (3) |
C15 | 0.085 (3) | 0.085 (3) | 0.071 (3) | −0.012 (2) | 0.003 (2) | 0.000 (2) |
C16 | 0.074 (2) | 0.068 (2) | 0.075 (2) | 0.0018 (19) | 0.012 (2) | 0.006 (2) |
C17 | 0.109 (3) | 0.153 (4) | 0.081 (3) | 0.001 (3) | 0.017 (2) | −0.036 (3) |
N—C10 | 1.357 (4) | C7—H7B | 0.9600 |
N—C11 | 1.421 (4) | C7—H7C | 0.9600 |
N—H0A | 0.8600 | C8—H8A | 0.9600 |
O1—C2 | 1.219 (4) | C8—H8B | 0.9600 |
C1—C2 | 1.510 (5) | C8—H8C | 0.9600 |
C1—H1A | 0.9600 | C9—C10 | 1.497 (4) |
C1—H1B | 0.9600 | C9—H9A | 0.9700 |
C1—H1C | 0.9600 | C9—H9B | 0.9700 |
O2—C10 | 1.217 (3) | C11—C16 | 1.374 (4) |
C2—C3 | 1.495 (4) | C11—C12 | 1.384 (4) |
C3—C6 | 1.521 (4) | C12—C13 | 1.376 (5) |
C3—C4 | 1.574 (4) | C12—H12A | 0.9300 |
C3—H3A | 0.9800 | C13—C14 | 1.347 (5) |
C4—C8 | 1.512 (4) | C13—H13A | 0.9300 |
C4—C7 | 1.522 (4) | C14—C15 | 1.411 (5) |
C4—C5 | 1.573 (4) | C14—H14A | 0.9300 |
C5—C6 | 1.516 (4) | C15—C16 | 1.399 (4) |
C5—C9 | 1.523 (4) | C15—C17 | 1.504 (5) |
C5—H5A | 0.9800 | C16—H16A | 0.9300 |
C6—H6A | 0.9700 | C17—H17A | 0.9600 |
C6—H6B | 0.9700 | C17—H17B | 0.9600 |
C7—H7A | 0.9600 | C17—H17C | 0.9600 |
C10—N—C11 | 126.3 (3) | H7B—C7—H7C | 109.5 |
C10—N—H0A | 116.9 | C4—C8—H8A | 109.5 |
C11—N—H0A | 116.9 | C4—C8—H8B | 109.5 |
C2—C1—H1A | 109.5 | H8A—C8—H8B | 109.5 |
C2—C1—H1B | 109.5 | C4—C8—H8C | 109.5 |
H1A—C1—H1B | 109.5 | H8A—C8—H8C | 109.5 |
C2—C1—H1C | 109.5 | H8B—C8—H8C | 109.5 |
H1A—C1—H1C | 109.5 | C10—C9—C5 | 113.7 (3) |
H1B—C1—H1C | 109.5 | C10—C9—H9A | 108.8 |
O1—C2—C3 | 121.8 (4) | C5—C9—H9A | 108.8 |
O1—C2—C1 | 122.5 (4) | C10—C9—H9B | 108.8 |
C3—C2—C1 | 115.7 (4) | C5—C9—H9B | 108.8 |
C2—C3—C6 | 120.0 (3) | H9A—C9—H9B | 107.7 |
C2—C3—C4 | 116.1 (3) | O2—C10—N | 124.0 (3) |
C6—C3—C4 | 88.9 (2) | O2—C10—C9 | 121.9 (3) |
C2—C3—H3A | 110.1 | N—C10—C9 | 114.0 (3) |
C6—C3—H3A | 110.1 | C16—C11—C12 | 120.7 (4) |
C4—C3—H3A | 110.1 | C16—C11—N | 116.9 (3) |
C8—C4—C7 | 112.0 (3) | C12—C11—N | 122.3 (3) |
C8—C4—C3 | 112.7 (3) | C13—C12—C11 | 117.0 (4) |
C7—C4—C3 | 115.2 (3) | C13—C12—H12A | 121.5 |
C8—C4—C5 | 113.0 (3) | C11—C12—H12A | 121.5 |
C7—C4—C5 | 115.5 (3) | C14—C13—C12 | 123.4 (4) |
C3—C4—C5 | 86.1 (2) | C14—C13—H13A | 118.3 |
C6—C5—C9 | 119.3 (3) | C12—C13—H13A | 118.3 |
C6—C5—C4 | 89.1 (2) | C13—C14—C15 | 120.8 (4) |
C9—C5—C4 | 120.0 (3) | C13—C14—H14A | 119.6 |
C6—C5—H5A | 108.9 | C15—C14—H14A | 119.6 |
C9—C5—H5A | 108.9 | C16—C15—C14 | 115.9 (3) |
C4—C5—H5A | 108.9 | C16—C15—C17 | 120.9 (4) |
C3—C6—C5 | 90.0 (2) | C14—C15—C17 | 123.2 (4) |
C3—C6—H6A | 113.6 | C11—C16—C15 | 122.2 (3) |
C5—C6—H6A | 113.6 | C11—C16—H16A | 118.9 |
C3—C6—H6B | 113.6 | C15—C16—H16A | 118.9 |
C5—C6—H6B | 113.6 | C15—C17—H17A | 109.5 |
H6A—C6—H6B | 110.9 | C15—C17—H17B | 109.5 |
C4—C7—H7A | 109.5 | H17A—C17—H17B | 109.5 |
C4—C7—H7B | 109.5 | C15—C17—H17C | 109.5 |
H7A—C7—H7B | 109.5 | H17A—C17—H17C | 109.5 |
C4—C7—H7C | 109.5 | H17B—C17—H17C | 109.5 |
H7A—C7—H7C | 109.5 | ||
O1—C2—C3—C6 | −7.8 (5) | C4—C5—C6—C3 | −18.5 (2) |
C1—C2—C3—C6 | 173.1 (3) | C6—C5—C9—C10 | 172.5 (3) |
O1—C2—C3—C4 | 97.1 (4) | C4—C5—C9—C10 | 64.8 (4) |
C1—C2—C3—C4 | −82.0 (4) | C11—N—C10—O2 | −0.5 (5) |
C2—C3—C4—C8 | −27.7 (4) | C11—N—C10—C9 | 179.7 (3) |
C6—C3—C4—C8 | 95.5 (3) | C5—C9—C10—O2 | 40.0 (5) |
C2—C3—C4—C7 | 102.6 (4) | C5—C9—C10—N | −140.2 (3) |
C6—C3—C4—C7 | −134.3 (3) | C10—N—C11—C16 | 149.2 (3) |
C2—C3—C4—C5 | −141.0 (3) | C10—N—C11—C12 | −34.2 (5) |
C6—C3—C4—C5 | −17.8 (2) | C16—C11—C12—C13 | −3.5 (5) |
C8—C4—C5—C6 | −95.2 (3) | N—C11—C12—C13 | −180.0 (3) |
C7—C4—C5—C6 | 134.0 (3) | C11—C12—C13—C14 | 2.1 (6) |
C3—C4—C5—C6 | 17.9 (2) | C12—C13—C14—C15 | 0.5 (6) |
C8—C4—C5—C9 | 28.6 (4) | C13—C14—C15—C16 | −1.6 (5) |
C7—C4—C5—C9 | −102.2 (3) | C13—C14—C15—C17 | −179.5 (4) |
C3—C4—C5—C9 | 141.7 (3) | C12—C11—C16—C15 | 2.5 (5) |
C2—C3—C6—C5 | 138.2 (3) | N—C11—C16—C15 | 179.1 (3) |
C4—C3—C6—C5 | 18.5 (2) | C14—C15—C16—C11 | 0.2 (5) |
C9—C5—C6—C3 | −142.9 (3) | C17—C15—C16—C11 | 178.1 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N—H0A···O2i | 0.86 | 2.04 | 2.892 (4) | 169 |
C12—H12A···O2 | 0.93 | 2.49 | 2.931 (5) | 109 |
C13—H13A···O1ii | 0.93 | 2.55 | 3.440 (5) | 161 |
Symmetry codes: (i) x+1, −y−3/2, z−1/2; (ii) x+3/2, −y+1/2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C17H23NO2 |
Mr | 273.36 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 293 |
a, b, c (Å) | 12.513 (3), 9.5190 (19), 26.844 (5) |
V (Å3) | 3197.4 (11) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.40 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.951, 0.975 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3150, 3120, 1385 |
Rint | 0.032 |
(sin θ/λ)max (Å−1) | 0.616 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.073, 0.170, 1.04 |
No. of reflections | 3120 |
No. of parameters | 181 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.14, −0.14 |
Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).
D—H···A | D—H | H···A | D···A | D—H···A |
N—H0A···O2i | 0.86 | 2.04 | 2.892 (4) | 169 |
C12—H12A···O2 | 0.93 | 2.49 | 2.931 (5) | 109 |
C13—H13A···O1ii | 0.93 | 2.55 | 3.440 (5) | 161 |
Symmetry codes: (i) x+1, −y−3/2, z−1/2; (ii) x+3/2, −y+1/2, −z+1. |
Acknowledgements
This work was supported by the National Key Technology R&D Programme of China under grant No. 2006BAD06B10.
References
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Terpenes are convenient chiral precursors due to their availability and low cost, and among them, a-pinene (both enantiomers) and verbenone are prominent. For instance, pinene has been used as starting material for the production of some compounds of industrial interest (Mitra & Khanra, 1977). Chiral cyclobutane compound, pinonic acid, can be synthesized from a-pinene. Many derivatives of pinonic acid have interesting biological properties. So we synthesized several derivatives of pinonic acid. In our previous paper we have reported the crystal structure of 2-[(1S,3S)-3-acetyl-2,2-dimethylcyclobutyl]-N-(2,6-difluorophenyl) acetamide (Yin et al., 2007). Now we synthesized the title compound (I) and report here its crystal structure.
The molecular structure of (I) is shown in Fig. 1. A l l bond lengths and angles are normal. The crystal structure is stabilized by N—H···O and C—H···O hydrogen bonding interactions (Table 1).