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Acta Crystallogr Sect E Struct Rep Online. 2009 July 1; 65(Pt 7): o1618.
Published online 2009 June 20. doi:  10.1107/S1600536809022260
PMCID: PMC2969475

1-[1-(Hydroxy­imino)eth­yl]-N-(2-methoxy­phen­yl)cyclo­propane­carboxamide

Abstract

The title compound, C13H16N2O3, adopts an E configuration with respect to the C=N bond and an intra­molecular N—H(...)N hydrogen bond results in the formation of a six-membered ring. In the crystal, inter­molecular O—H(...)O hydrogen bonds link the mol­ecules into a chain propagating along the b axis. Very weak π–π stacking inter­actions [centroid–centroid distance = 4.18 (2) Å] may further consolidate the packing, forming a two-dimensional supra­molecular network.

Related literature

For background to cyclo­propane derivatives, see: Liu & Montgomery (2006 [triangle]); Ogoshi et al. (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1618-scheme1.jpg

Experimental

Crystal data

  • C13H16N2O3
  • M r = 248.28
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1618-efi1.jpg
  • a = 16.062 (6) Å
  • b = 5.483 (2) Å
  • c = 14.250 (6) Å
  • β = 100.055 (6)°
  • V = 1235.7 (8) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 293 K
  • 0.41 × 0.29 × 0.20 mm

Data collection

  • Bruker SMART APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 1999 [triangle]) T min = 0.96, T max = 0.99
  • 6430 measured reflections
  • 2432 independent reflections
  • 1520 reflections with I > 2σ(I)
  • R int = 0.044

Refinement

  • R[F 2 > 2σ(F 2)] = 0.073
  • wR(F 2) = 0.170
  • S = 1.09
  • 2432 reflections
  • 169 parameters
  • 2 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.21 e Å−3
  • Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 1999 [triangle]); cell refinement: SAINT (Bruker, 1999 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809022260/hb2995sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022260/hb2995Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank the College of Chemical Engineering of Shanxi Datong University for support.

supplementary crystallographic information

Comment

Cyclopropane and their derivatives are a significant class of compounds which can be used in a variety of studies such as organic synthesis, catalytic reaction and so on (Liu & Montgomery, 2006; Ogoshi et al., 2006). In order to extend our work on structural characterization of cyclopropane compounds, we report the synthesis and the X-ray structure of the title compound, (I), in this paper (Fig. 1).

The title molecule adopts an E configuration with respect to C=N bond. There is an intramolecular O—H···N hydrogen bonds, forming of a six-membered ring (Table 1) and the intermolecular O—H···O hydrogen bonds link the molecules into a one-dimensional chain along the b axis. The crystal structure is further stabilized by π-π interaction involving the benzene rings: Cg1···Cg1 (1 - x, 1 - y, 1 - z) = 4.18 (2) Å, where Cg1 denotes the centroid of the C2—C7 (Fig. 2).

Experimental

To a solution of 1-acetyl-N-(2-methoxyphenyl)cyclopropanecarboxamide (2.33 g, 10 mmol) and NaOAc (1.64 g, 20 mmol) in EtOH (25 ml) and H2O (1 ml) was added NH2OH.HCl (1.39 g, 20 mmol) in one portion. The reaction mixture was stirred at room temperature for 12 h, and then poured into ice-water (200 ml) under stirring. A white solid was precipitated, which was filtered and the residue was purified by a flash silica gel column chromatography to give colourless blocks of (I) (eluent: ether/ethyl acetate = 1/3 v/v).

Refinement

The N- and O-bound H atoms were located in a difference map and their positions were freely refined. The C-bound H atoms were geometrically placed (C—H = 0.93–0.97Å) and refined as riding. The constraints Uiso = 1.2Ueq(C,N) or 1.5Ueq(methyl C,O) were applied.

Figures

Fig. 1.
Molecule structure of (I) with displacement ellipsoids drawn at the 30% probability level for non-H atoms.
Fig. 2.
View of the two-dimensional supramolecular structure of (I): hydrogen bonds and π-π interactions are shown as dashed lines.

Crystal data

C13H16N2O3F(000) = 528
Mr = 248.28Dx = 1.335 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybcCell parameters from 2432 reflections
a = 16.062 (6) Åθ = 1.3–26.1°
b = 5.483 (2) ŵ = 0.10 mm1
c = 14.250 (6) ÅT = 293 K
β = 100.055 (6)°Block, colourless
V = 1235.7 (8) Å30.41 × 0.29 × 0.20 mm
Z = 4

Data collection

Bruker SMART APEX CCD diffractometer2432 independent reflections
Radiation source: fine-focus sealed tube1520 reflections with I > 2σ(I)
graphiteRint = 0.044
ω scansθmax = 26.1°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 1999)h = −9→19
Tmin = 0.96, Tmax = 0.99k = −6→6
6430 measured reflectionsl = −17→17

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.073Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.170H atoms treated by a mixture of independent and constrained refinement
S = 1.09w = 1/[σ2(Fo2) + (0.0648P)2 + 0.566P] where P = (Fo2 + 2Fc2)/3
2432 reflections(Δ/σ)max < 0.001
169 parametersΔρmax = 0.21 e Å3
2 restraintsΔρmin = −0.20 e Å3

Special details

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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)

xyzUiso*/Ueq
C10.3277 (2)−0.2371 (7)1.1123 (2)0.0577 (10)
H1A0.2878−0.22491.15500.087*
H1B0.3826−0.18741.14470.087*
H1C0.3303−0.40291.09140.087*
C20.3509 (2)−0.0767 (6)0.9634 (2)0.0428 (8)
C30.4169 (2)−0.2323 (6)0.9573 (3)0.0558 (10)
H30.4305−0.35611.00200.067*
C40.4628 (2)−0.2049 (7)0.8849 (3)0.0578 (10)
H40.5075−0.30990.88120.069*
C50.4432 (2)−0.0246 (6)0.8182 (2)0.0525 (9)
H50.4745−0.00760.76960.063*
C60.3768 (2)0.1321 (6)0.8233 (2)0.0468 (8)
H60.36370.25480.77810.056*
C70.3297 (2)0.1078 (5)0.8954 (2)0.0378 (7)
C80.21464 (19)0.4042 (5)0.8447 (2)0.0365 (7)
C90.14682 (19)0.5534 (5)0.8782 (2)0.0356 (7)
C100.0684 (2)0.5852 (6)0.8000 (2)0.0516 (9)
H10A0.06710.49750.74060.062*
H10B0.01390.60220.81980.062*
C110.1292 (2)0.7886 (6)0.8211 (2)0.0500 (9)
H11A0.11160.92990.85370.060*
H11B0.16470.82520.77450.060*
C120.13045 (19)0.5525 (5)0.9782 (2)0.0366 (7)
C130.0787 (2)0.7537 (6)1.0116 (3)0.0559 (10)
H13A0.07400.72631.07700.084*
H13B0.02330.75530.97310.084*
H13C0.10590.90761.00590.084*
N20.16185 (17)0.3782 (4)1.03227 (17)0.0405 (7)
O10.30181 (15)−0.0837 (4)1.03230 (16)0.0589 (7)
O20.22453 (15)0.4164 (4)0.76124 (15)0.0523 (6)
O30.14111 (17)0.3914 (4)1.12368 (16)0.0580 (7)
H3O0.176 (2)0.300 (7)1.159 (3)0.087*
N10.26309 (17)0.2616 (4)0.90914 (18)0.0392 (7)
H1N0.2470 (19)0.254 (6)0.9632 (16)0.047*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.067 (3)0.060 (2)0.048 (2)0.008 (2)0.0146 (18)0.0174 (18)
C20.051 (2)0.0407 (17)0.0392 (18)0.0018 (16)0.0135 (15)−0.0005 (15)
C30.061 (2)0.050 (2)0.057 (2)0.0181 (19)0.0139 (19)0.0073 (17)
C40.058 (2)0.056 (2)0.064 (3)0.0165 (19)0.0211 (19)−0.0074 (19)
C50.055 (2)0.059 (2)0.049 (2)0.0000 (19)0.0237 (17)−0.0093 (18)
C60.054 (2)0.0429 (18)0.046 (2)−0.0002 (17)0.0155 (17)−0.0008 (15)
C70.045 (2)0.0327 (16)0.0372 (17)−0.0028 (15)0.0115 (14)−0.0061 (14)
C80.046 (2)0.0311 (15)0.0317 (17)−0.0094 (15)0.0058 (14)−0.0012 (13)
C90.0413 (18)0.0258 (14)0.0394 (17)−0.0050 (14)0.0064 (14)0.0022 (13)
C100.049 (2)0.053 (2)0.050 (2)0.0036 (18)0.0013 (16)0.0030 (17)
C110.065 (2)0.0338 (17)0.051 (2)0.0036 (17)0.0092 (18)0.0139 (15)
C120.0402 (19)0.0257 (14)0.0444 (18)−0.0048 (14)0.0089 (14)−0.0011 (13)
C130.068 (3)0.0383 (19)0.067 (3)0.0096 (18)0.026 (2)−0.0046 (17)
N20.0562 (18)0.0345 (14)0.0336 (14)0.0018 (13)0.0154 (12)0.0017 (12)
O10.0641 (17)0.0655 (16)0.0524 (15)0.0226 (13)0.0245 (12)0.0235 (12)
O20.0684 (16)0.0570 (15)0.0329 (13)0.0035 (13)0.0128 (11)0.0033 (11)
O30.0794 (19)0.0602 (16)0.0402 (14)0.0181 (14)0.0264 (12)0.0069 (11)
N10.0509 (17)0.0354 (13)0.0334 (15)0.0070 (13)0.0133 (13)0.0018 (12)

Geometric parameters (Å, °)

C1—O11.420 (4)C8—C91.505 (4)
C1—H1A0.9600C9—C121.494 (4)
C1—H1B0.9600C9—C111.525 (4)
C1—H1C0.9600C9—C101.540 (4)
C2—O11.362 (4)C10—C111.478 (5)
C2—C31.376 (4)C10—H10A0.9700
C2—C71.402 (4)C10—H10B0.9700
C3—C41.377 (5)C11—H11A0.9700
C3—H30.9300C11—H11B0.9700
C4—C51.369 (5)C12—N21.275 (4)
C4—H40.9300C12—C131.507 (4)
C5—C61.380 (5)C13—H13A0.9600
C5—H50.9300C13—H13B0.9600
C6—C71.385 (4)C13—H13C0.9600
C6—H60.9300N2—O31.402 (3)
C7—N11.402 (4)O3—H3O0.85 (4)
C8—O21.229 (3)N1—H1N0.856 (17)
C8—N11.345 (4)
O1—C1—H1A109.5C12—C9—C10115.7 (3)
O1—C1—H1B109.5C8—C9—C10112.2 (3)
H1A—C1—H1B109.5C11—C9—C1057.7 (2)
O1—C1—H1C109.5C11—C10—C960.6 (2)
H1A—C1—H1C109.5C11—C10—H10A117.7
H1B—C1—H1C109.5C9—C10—H10A117.7
O1—C2—C3125.3 (3)C11—C10—H10B117.7
O1—C2—C7114.7 (3)C9—C10—H10B117.7
C3—C2—C7120.0 (3)H10A—C10—H10B114.8
C2—C3—C4120.0 (3)C10—C11—C961.7 (2)
C2—C3—H3120.0C10—C11—H11A117.6
C4—C3—H3120.0C9—C11—H11A117.6
C5—C4—C3120.7 (3)C10—C11—H11B117.6
C5—C4—H4119.6C9—C11—H11B117.6
C3—C4—H4119.6H11A—C11—H11B114.7
C4—C5—C6119.9 (3)N2—C12—C9117.5 (3)
C4—C5—H5120.0N2—C12—C13122.7 (3)
C6—C5—H5120.0C9—C12—C13119.8 (3)
C5—C6—C7120.4 (3)C12—C13—H13A109.5
C5—C6—H6119.8C12—C13—H13B109.5
C7—C6—H6119.8H13A—C13—H13B109.5
C6—C7—C2119.0 (3)C12—C13—H13C109.5
C6—C7—N1125.1 (3)H13A—C13—H13C109.5
C2—C7—N1115.9 (3)H13B—C13—H13C109.5
O2—C8—N1122.3 (3)C12—N2—O3112.9 (2)
O2—C8—C9120.0 (3)C2—O1—C1118.0 (3)
N1—C8—C9117.7 (2)N2—O3—H3O107 (3)
C12—C9—C8123.9 (3)C8—N1—C7128.2 (3)
C12—C9—C11117.6 (3)C8—N1—H1N114 (2)
C8—C9—C11111.6 (3)C7—N1—H1N117 (2)
O1—C2—C3—C4−179.1 (3)C8—C9—C10—C11−102.3 (3)
C7—C2—C3—C40.8 (5)C12—C9—C11—C10−104.3 (3)
C2—C3—C4—C5−0.4 (6)C8—C9—C11—C10103.3 (3)
C3—C4—C5—C60.1 (6)C8—C9—C12—N2−16.4 (4)
C4—C5—C6—C7−0.2 (5)C11—C9—C12—N2−165.1 (3)
C5—C6—C7—C20.6 (5)C10—C9—C12—N2129.6 (3)
C5—C6—C7—N1177.7 (3)C8—C9—C12—C13163.4 (3)
O1—C2—C7—C6179.0 (3)C11—C9—C12—C1314.7 (4)
C3—C2—C7—C6−0.9 (5)C10—C9—C12—C13−50.6 (4)
O1—C2—C7—N11.7 (4)C9—C12—N2—O3−178.6 (2)
C3—C2—C7—N1−178.2 (3)C13—C12—N2—O31.7 (4)
O2—C8—C9—C12−179.5 (3)C3—C2—O1—C110.3 (5)
N1—C8—C9—C120.1 (4)C7—C2—O1—C1−169.6 (3)
O2—C8—C9—C11−29.2 (4)O2—C8—N1—C7−0.4 (5)
N1—C8—C9—C11150.4 (3)C9—C8—N1—C7−179.9 (3)
O2—C8—C9—C1033.5 (4)C6—C7—N1—C823.1 (5)
N1—C8—C9—C10−146.9 (3)C2—C7—N1—C8−159.8 (3)
C12—C9—C10—C11107.8 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1N···N20.86 (2)1.94 (2)2.670 (3)142 (3)
O3—H3O···O2i0.85 (4)1.93 (2)2.751 (3)162 (4)

Symmetry codes: (i) x, −y+1/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2995).

References

  • Bruker (1999). SMART, SAINT and SADABSBruker AXS Inc., Madison, Wisconsin, USA.
  • Liu, L. & Montgomery, J. (2006). J. Am. Chem. Soc.128, 5348–5349. [PubMed]
  • Ogoshi, S., Nagata, M. & Kurosawa, H. (2006). J. Am. Chem. Soc.128, 5350–5351. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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