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In the title compound, C15H17NO2, the six-membered cyclo­hexene ring has an envelope conformation. The structure is stabilized by O—H...N hydrogen bonds and weak van der Waals inter­actions. There are no C—H...π or π–π inter­actions between the two ring systems; however, there is an inter­molecular C—H...O hydrogen bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806049713/jh2044sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806049713/jh2044Isup2.hkl
Contains datablock I

CCDC reference: 630034

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.063
  • wR factor = 0.192
  • Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT128_ALERT_4_C Non-standard setting of Space group P21/c .... P21/a PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C7 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C15
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 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 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996); program(s) used to solve structure: SHELXS (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

3-Acetyl-2-(4-methylphenyl)cyclohex-2-en-1-one oxime top
Crystal data top
C15H17NO2F(000) = 520
Mr = 243.30Dx = 1.177 Mg m3
Monoclinic, P21/aMo Kα radiation, λ = 0.71073 Å
a = 9.205 (4) ÅCell parameters from 25 reflections
b = 11.311 (4) Åθ = 2.4–25°
c = 13.489 (5) ŵ = 0.08 mm1
β = 102.19 (3)°T = 293 K
V = 1372.7 (9) Å3Block, colourless
Z = 40.28 × 0.14 × 0.12 mm
Data collection top
Nonius MACH3 four-circle
diffractometer
1584 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.049
Graphite monochromatorθmax = 25.0°, θmin = 2.4°
ω scansh = 010
Absorption correction: ψ scan
(North et al., 1968)
k = 013
Tmin = 0.987, Tmax = 0.991l = 1615
2574 measured reflections3 standard reflections every 60 min
2407 independent reflections intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.192H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.1097P)2 + 0.2444P]
where P = (Fo2 + 2Fc2)/3
2407 reflections(Δ/σ)max < 0.001
163 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.22 e Å3
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
xyzUiso*/Ueq
N10.1030 (2)0.4053 (2)0.04749 (15)0.0491 (6)
C20.2607 (3)0.3455 (2)0.19911 (18)0.0406 (6)
O10.0330 (2)0.37410 (19)0.05194 (13)0.0655 (7)
H10.01510.43050.07960.098*
C90.2546 (3)0.4685 (2)0.23871 (17)0.0407 (6)
C10.1805 (3)0.3206 (2)0.09463 (18)0.0443 (7)
C100.1909 (3)0.4909 (2)0.32113 (18)0.0459 (7)
H100.14970.42900.35130.055*
C30.3336 (3)0.2569 (2)0.25651 (18)0.0431 (6)
C70.4228 (3)0.2741 (3)0.36149 (19)0.0494 (7)
C140.3145 (3)0.5632 (3)0.1951 (2)0.0519 (7)
H140.35620.55060.13890.062*
O20.4185 (3)0.1986 (2)0.42448 (15)0.0840 (8)
C40.3272 (3)0.1304 (2)0.2196 (2)0.0561 (8)
H4A0.41930.11180.19890.067*
H4B0.31920.07830.27530.067*
C110.1881 (3)0.6046 (3)0.3591 (2)0.0557 (8)
H110.14460.61800.41440.067*
C130.3125 (4)0.6755 (3)0.2341 (2)0.0611 (8)
H130.35490.73730.20460.073*
C60.1907 (4)0.1999 (3)0.0509 (2)0.0650 (9)
H6A0.27810.19540.02150.078*
H6B0.10390.18550.00250.078*
C120.2489 (3)0.6983 (3)0.3160 (2)0.0597 (8)
C80.5295 (3)0.3751 (3)0.3876 (2)0.0678 (9)
H8A0.57550.37180.45840.102*
H8B0.47690.44850.37310.102*
H8C0.60450.36970.34800.102*
C50.2002 (4)0.1069 (3)0.1328 (2)0.0671 (9)
H5A0.10820.10620.15700.081*
H5B0.21250.02960.10450.081*
C150.2448 (5)0.8223 (3)0.3580 (3)0.0922 (13)
H15A0.19590.82100.41420.138*
H15B0.19150.87350.30610.138*
H15C0.34450.85110.38040.138*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0528 (14)0.0509 (14)0.0393 (11)0.0083 (11)0.0001 (10)0.0020 (10)
C20.0360 (13)0.0425 (15)0.0433 (13)0.0035 (11)0.0083 (10)0.0026 (11)
O10.0736 (15)0.0673 (14)0.0447 (10)0.0190 (11)0.0122 (10)0.0062 (9)
C90.0392 (14)0.0392 (14)0.0387 (12)0.0030 (11)0.0027 (10)0.0021 (10)
C10.0446 (15)0.0455 (15)0.0410 (13)0.0090 (12)0.0054 (11)0.0002 (11)
C100.0419 (15)0.0479 (16)0.0463 (14)0.0047 (12)0.0058 (11)0.0017 (12)
C30.0386 (14)0.0422 (15)0.0485 (14)0.0029 (12)0.0093 (11)0.0035 (12)
C70.0434 (15)0.0565 (18)0.0467 (14)0.0121 (13)0.0061 (11)0.0099 (13)
C140.0578 (17)0.0480 (17)0.0486 (15)0.0006 (13)0.0085 (13)0.0088 (12)
O20.0982 (19)0.0863 (18)0.0585 (13)0.0103 (14)0.0038 (12)0.0280 (12)
C40.0605 (18)0.0434 (17)0.0625 (17)0.0100 (14)0.0088 (14)0.0046 (13)
C110.0491 (17)0.0585 (19)0.0577 (17)0.0016 (14)0.0070 (13)0.0162 (14)
C130.075 (2)0.0394 (17)0.0620 (18)0.0053 (15)0.0017 (15)0.0096 (14)
C60.075 (2)0.060 (2)0.0531 (16)0.0227 (16)0.0042 (15)0.0131 (14)
C120.0608 (19)0.0406 (16)0.0677 (19)0.0048 (14)0.0089 (15)0.0063 (14)
C80.0521 (18)0.074 (2)0.0683 (19)0.0014 (16)0.0086 (15)0.0018 (16)
C50.076 (2)0.0452 (18)0.074 (2)0.0081 (15)0.0010 (16)0.0147 (15)
C150.111 (3)0.047 (2)0.109 (3)0.007 (2)0.000 (2)0.0181 (19)
Geometric parameters (Å, º) top
N1—C11.280 (3)C4—H4A0.9700
N1—O11.405 (3)C4—H4B0.9700
C2—C31.355 (3)C11—C121.383 (4)
C2—C11.473 (3)C11—H110.9300
C2—C91.495 (4)C13—C121.381 (4)
O1—H10.8200C13—H130.9300
C9—C101.385 (4)C6—C51.515 (4)
C9—C141.391 (4)C6—H6A0.9700
C1—C61.498 (4)C6—H6B0.9700
C10—C111.386 (4)C12—C151.516 (4)
C10—H100.9300C8—H8A0.9600
C3—C71.492 (4)C8—H8B0.9600
C3—C41.512 (4)C8—H8C0.9600
C7—O21.212 (3)C5—H5A0.9700
C7—C81.499 (4)C5—H5B0.9700
C14—C131.376 (4)C15—H15A0.9600
C14—H140.9300C15—H15B0.9600
C4—C51.493 (4)C15—H15C0.9600
C1—N1—O1112.4 (2)C10—C11—H11119.5
C3—C2—C1119.5 (2)C14—C13—C12121.4 (3)
C3—C2—C9122.4 (2)C14—C13—H13119.3
C1—C2—C9118.1 (2)C12—C13—H13119.3
N1—O1—H1109.5C1—C6—C5110.1 (2)
C10—C9—C14118.1 (2)C1—C6—H6A109.6
C10—C9—C2120.7 (2)C5—C6—H6A109.6
C14—C9—C2121.2 (2)C1—C6—H6B109.6
N1—C1—C2116.5 (2)C5—C6—H6B109.6
N1—C1—C6124.1 (2)H6A—C6—H6B108.2
C2—C1—C6119.4 (2)C13—C12—C11118.1 (3)
C9—C10—C11120.7 (3)C13—C12—C15121.4 (3)
C9—C10—H10119.6C11—C12—C15120.5 (3)
C11—C10—H10119.6C7—C8—H8A109.5
C2—C3—C7123.5 (2)C7—C8—H8B109.5
C2—C3—C4122.1 (2)H8A—C8—H8B109.5
C7—C3—C4114.3 (2)C7—C8—H8C109.5
O2—C7—C3118.7 (3)H8A—C8—H8C109.5
O2—C7—C8119.3 (3)H8B—C8—H8C109.5
C3—C7—C8121.7 (2)C4—C5—C6111.3 (3)
C13—C14—C9120.7 (3)C4—C5—H5A109.4
C13—C14—H14119.6C6—C5—H5A109.4
C9—C14—H14119.6C4—C5—H5B109.4
C5—C4—C3113.4 (2)C6—C5—H5B109.4
C5—C4—H4A108.9H5A—C5—H5B108.0
C3—C4—H4A108.9C12—C15—H15A109.5
C5—C4—H4B108.9C12—C15—H15B109.5
C3—C4—H4B108.9H15A—C15—H15B109.5
H4A—C4—H4B107.7C12—C15—H15C109.5
C12—C11—C10121.0 (3)H15A—C15—H15C109.5
C12—C11—H11119.5H15B—C15—H15C109.5
C3—C2—C9—C1060.8 (3)C4—C3—C7—O236.9 (4)
C1—C2—C9—C10117.5 (3)C2—C3—C7—C845.4 (4)
C3—C2—C9—C14118.2 (3)C4—C3—C7—C8136.2 (3)
C1—C2—C9—C1463.4 (3)C10—C9—C14—C131.1 (4)
O1—N1—C1—C2178.9 (2)C2—C9—C14—C13177.9 (2)
O1—N1—C1—C62.5 (4)C2—C3—C4—C518.3 (4)
C3—C2—C1—N1174.0 (2)C7—C3—C4—C5160.1 (3)
C9—C2—C1—N14.4 (3)C9—C10—C11—C120.2 (4)
C3—C2—C1—C64.7 (4)C9—C14—C13—C121.3 (4)
C9—C2—C1—C6176.9 (3)N1—C1—C6—C5144.0 (3)
C14—C9—C10—C110.4 (4)C2—C1—C6—C534.6 (4)
C2—C9—C10—C11178.7 (2)C14—C13—C12—C110.7 (4)
C1—C2—C3—C7177.5 (2)C14—C13—C12—C15179.1 (3)
C9—C2—C3—C74.2 (4)C10—C11—C12—C130.0 (4)
C1—C2—C3—C44.3 (4)C10—C11—C12—C15179.9 (3)
C9—C2—C3—C4174.1 (2)C3—C4—C5—C648.4 (4)
C2—C3—C7—O2141.5 (3)C1—C6—C5—C455.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N1i0.822.112.798 (3)142
Symmetry code: (i) x, y+1, z.
 

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