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

Wang, J.-L.; Meng, S.-M.; Tian, M.-Z.; Feng, F.

doi:10.1107/S1600536809022260

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page o1618

doi:10.1107/S1600536809022260

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

Jun-Ling Wang,^a ^* Shuang-Ming Meng,^a Mao-Zhong Tian ^a and Feng Feng ^a

^aCollege of Chemical Engineering, Shanxi Datong University, Datong 037009, People's Republic of China
^*Correspondence e-mail: junlingwang2009@163.com

(Received 30 May 2009; accepted 11 June 2009; online 20 June 2009)

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 ); Ogoshi et al. (2006 ).

Experimental

Crystal data

C₁₃H₁₆N₂O₃
M_r = 248.28
Monoclinic, P 2₁ /c
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 ) 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[F² > 2σ(F²)] = 0.073
wR(F²) = 0.170
S = 1.09
2432 reflections
169 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯N2	0.856 (17)	1.94 (2)	2.670 (3)	142 (3)
O3—H3O⋯O2ⁱ	0.85 (4)	1.93 (2)	2.751 (3)	162 (4)
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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

Supporting information

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

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

checkCIF report

Comment top

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).

Related literature top

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

Experimental top

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).

Computing details top

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

Figures top

	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.

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

Crystal data top

C₁₃H₁₆N₂O₃	F(000) = 528
M_r = 248.28	D_x = 1.335 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 2432 reflections
a = 16.062 (6) Å	θ = 1.3–26.1°
b = 5.483 (2) Å	µ = 0.10 mm⁻¹
c = 14.250 (6) Å	T = 293 K
β = 100.055 (6)°	Block, colourless
V = 1235.7 (8) Å³	0.41 × 0.29 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEX CCD diffractometer	2432 independent reflections
Radiation source: fine-focus sealed tube	1520 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
ω scans	θ_max = 26.1°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −9→19
T_min = 0.96, T_max = 0.99	k = −6→6
6430 measured reflections	l = −17→17

Refinement top

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 atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.0648P)² + 0.566P] where P = (F_o² + 2F_c²)/3
2432 reflections	(Δ/σ)_max < 0.001
169 parameters	Δρ_max = 0.21 e Å⁻³
2 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₃H₁₆N₂O₃	V = 1235.7 (8) Å³
M_r = 248.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.062 (6) Å	µ = 0.10 mm⁻¹
b = 5.483 (2) Å	T = 293 K
c = 14.250 (6) Å	0.41 × 0.29 × 0.20 mm
β = 100.055 (6)°

Data collection top

Bruker SMART APEX CCD diffractometer	2432 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1999)	1520 reflections with I > 2σ(I)
T_min = 0.96, T_max = 0.99	R_int = 0.044
6430 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.073	2 restraints
wR(F²) = 0.170	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.21 e Å⁻³
2432 reflections	Δρ_min = −0.20 e Å⁻³
169 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
C1	0.3277 (2)	−0.2371 (7)	1.1123 (2)	0.0577 (10)
H1A	0.2878	−0.2249	1.1550	0.087*
H1B	0.3826	−0.1874	1.1447	0.087*
H1C	0.3303	−0.4029	1.0914	0.087*
C2	0.3509 (2)	−0.0767 (6)	0.9634 (2)	0.0428 (8)
C3	0.4169 (2)	−0.2323 (6)	0.9573 (3)	0.0558 (10)
H3	0.4305	−0.3561	1.0020	0.067*
C4	0.4628 (2)	−0.2049 (7)	0.8849 (3)	0.0578 (10)
H4	0.5075	−0.3099	0.8812	0.069*
C5	0.4432 (2)	−0.0246 (6)	0.8182 (2)	0.0525 (9)
H5	0.4745	−0.0076	0.7696	0.063*
C6	0.3768 (2)	0.1321 (6)	0.8233 (2)	0.0468 (8)
H6	0.3637	0.2548	0.7781	0.056*
C7	0.3297 (2)	0.1078 (5)	0.8954 (2)	0.0378 (7)
C8	0.21464 (19)	0.4042 (5)	0.8447 (2)	0.0365 (7)
C9	0.14682 (19)	0.5534 (5)	0.8782 (2)	0.0356 (7)
C10	0.0684 (2)	0.5852 (6)	0.8000 (2)	0.0516 (9)
H10A	0.0671	0.4975	0.7406	0.062*
H10B	0.0139	0.6022	0.8198	0.062*
C11	0.1292 (2)	0.7886 (6)	0.8211 (2)	0.0500 (9)
H11A	0.1116	0.9299	0.8537	0.060*
H11B	0.1647	0.8252	0.7745	0.060*
C12	0.13045 (19)	0.5525 (5)	0.9782 (2)	0.0366 (7)
C13	0.0787 (2)	0.7537 (6)	1.0116 (3)	0.0559 (10)
H13A	0.0740	0.7263	1.0770	0.084*
H13B	0.0233	0.7553	0.9731	0.084*
H13C	0.1059	0.9076	1.0059	0.084*
N2	0.16185 (17)	0.3782 (4)	1.03227 (17)	0.0405 (7)
O1	0.30181 (15)	−0.0837 (4)	1.03230 (16)	0.0589 (7)
O2	0.22453 (15)	0.4164 (4)	0.76124 (15)	0.0523 (6)
O3	0.14111 (17)	0.3914 (4)	1.12368 (16)	0.0580 (7)
H3O	0.176 (2)	0.300 (7)	1.159 (3)	0.087*
N1	0.26309 (17)	0.2616 (4)	0.90914 (18)	0.0392 (7)
H1N	0.2470 (19)	0.254 (6)	0.9632 (16)	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.067 (3)	0.060 (2)	0.048 (2)	0.008 (2)	0.0146 (18)	0.0174 (18)
C2	0.051 (2)	0.0407 (17)	0.0392 (18)	0.0018 (16)	0.0135 (15)	−0.0005 (15)
C3	0.061 (2)	0.050 (2)	0.057 (2)	0.0181 (19)	0.0139 (19)	0.0073 (17)
C4	0.058 (2)	0.056 (2)	0.064 (3)	0.0165 (19)	0.0211 (19)	−0.0074 (19)
C5	0.055 (2)	0.059 (2)	0.049 (2)	0.0000 (19)	0.0237 (17)	−0.0093 (18)
C6	0.054 (2)	0.0429 (18)	0.046 (2)	−0.0002 (17)	0.0155 (17)	−0.0008 (15)
C7	0.045 (2)	0.0327 (16)	0.0372 (17)	−0.0028 (15)	0.0115 (14)	−0.0061 (14)
C8	0.046 (2)	0.0311 (15)	0.0317 (17)	−0.0094 (15)	0.0058 (14)	−0.0012 (13)
C9	0.0413 (18)	0.0258 (14)	0.0394 (17)	−0.0050 (14)	0.0064 (14)	0.0022 (13)
C10	0.049 (2)	0.053 (2)	0.050 (2)	0.0036 (18)	0.0013 (16)	0.0030 (17)
C11	0.065 (2)	0.0338 (17)	0.051 (2)	0.0036 (17)	0.0092 (18)	0.0139 (15)
C12	0.0402 (19)	0.0257 (14)	0.0444 (18)	−0.0048 (14)	0.0089 (14)	−0.0011 (13)
C13	0.068 (3)	0.0383 (19)	0.067 (3)	0.0096 (18)	0.026 (2)	−0.0046 (17)
N2	0.0562 (18)	0.0345 (14)	0.0336 (14)	0.0018 (13)	0.0154 (12)	0.0017 (12)
O1	0.0641 (17)	0.0655 (16)	0.0524 (15)	0.0226 (13)	0.0245 (12)	0.0235 (12)
O2	0.0684 (16)	0.0570 (15)	0.0329 (13)	0.0035 (13)	0.0128 (11)	0.0033 (11)
O3	0.0794 (19)	0.0602 (16)	0.0402 (14)	0.0181 (14)	0.0264 (12)	0.0069 (11)
N1	0.0509 (17)	0.0354 (13)	0.0334 (15)	0.0070 (13)	0.0133 (13)	0.0018 (12)

Geometric parameters (Å, º) top

C1—O1	1.420 (4)	C8—C9	1.505 (4)
C1—H1A	0.9600	C9—C12	1.494 (4)
C1—H1B	0.9600	C9—C11	1.525 (4)
C1—H1C	0.9600	C9—C10	1.540 (4)
C2—O1	1.362 (4)	C10—C11	1.478 (5)
C2—C3	1.376 (4)	C10—H10A	0.9700
C2—C7	1.402 (4)	C10—H10B	0.9700
C3—C4	1.377 (5)	C11—H11A	0.9700
C3—H3	0.9300	C11—H11B	0.9700
C4—C5	1.369 (5)	C12—N2	1.275 (4)
C4—H4	0.9300	C12—C13	1.507 (4)
C5—C6	1.380 (5)	C13—H13A	0.9600
C5—H5	0.9300	C13—H13B	0.9600
C6—C7	1.385 (4)	C13—H13C	0.9600
C6—H6	0.9300	N2—O3	1.402 (3)
C7—N1	1.402 (4)	O3—H3O	0.85 (4)
C8—O2	1.229 (3)	N1—H1N	0.856 (17)
C8—N1	1.345 (4)

O1—C1—H1A	109.5	C12—C9—C10	115.7 (3)
O1—C1—H1B	109.5	C8—C9—C10	112.2 (3)
H1A—C1—H1B	109.5	C11—C9—C10	57.7 (2)
O1—C1—H1C	109.5	C11—C10—C9	60.6 (2)
H1A—C1—H1C	109.5	C11—C10—H10A	117.7
H1B—C1—H1C	109.5	C9—C10—H10A	117.7
O1—C2—C3	125.3 (3)	C11—C10—H10B	117.7
O1—C2—C7	114.7 (3)	C9—C10—H10B	117.7
C3—C2—C7	120.0 (3)	H10A—C10—H10B	114.8
C2—C3—C4	120.0 (3)	C10—C11—C9	61.7 (2)
C2—C3—H3	120.0	C10—C11—H11A	117.6
C4—C3—H3	120.0	C9—C11—H11A	117.6
C5—C4—C3	120.7 (3)	C10—C11—H11B	117.6
C5—C4—H4	119.6	C9—C11—H11B	117.6
C3—C4—H4	119.6	H11A—C11—H11B	114.7
C4—C5—C6	119.9 (3)	N2—C12—C9	117.5 (3)
C4—C5—H5	120.0	N2—C12—C13	122.7 (3)
C6—C5—H5	120.0	C9—C12—C13	119.8 (3)
C5—C6—C7	120.4 (3)	C12—C13—H13A	109.5
C5—C6—H6	119.8	C12—C13—H13B	109.5
C7—C6—H6	119.8	H13A—C13—H13B	109.5
C6—C7—C2	119.0 (3)	C12—C13—H13C	109.5
C6—C7—N1	125.1 (3)	H13A—C13—H13C	109.5
C2—C7—N1	115.9 (3)	H13B—C13—H13C	109.5
O2—C8—N1	122.3 (3)	C12—N2—O3	112.9 (2)
O2—C8—C9	120.0 (3)	C2—O1—C1	118.0 (3)
N1—C8—C9	117.7 (2)	N2—O3—H3O	107 (3)
C12—C9—C8	123.9 (3)	C8—N1—C7	128.2 (3)
C12—C9—C11	117.6 (3)	C8—N1—H1N	114 (2)
C8—C9—C11	111.6 (3)	C7—N1—H1N	117 (2)

O1—C2—C3—C4	−179.1 (3)	C8—C9—C10—C11	−102.3 (3)
C7—C2—C3—C4	0.8 (5)	C12—C9—C11—C10	−104.3 (3)
C2—C3—C4—C5	−0.4 (6)	C8—C9—C11—C10	103.3 (3)
C3—C4—C5—C6	0.1 (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—C2	0.6 (5)	C10—C9—C12—N2	129.6 (3)
C5—C6—C7—N1	177.7 (3)	C8—C9—C12—C13	163.4 (3)
O1—C2—C7—C6	179.0 (3)	C11—C9—C12—C13	14.7 (4)
C3—C2—C7—C6	−0.9 (5)	C10—C9—C12—C13	−50.6 (4)
O1—C2—C7—N1	1.7 (4)	C9—C12—N2—O3	−178.6 (2)
C3—C2—C7—N1	−178.2 (3)	C13—C12—N2—O3	1.7 (4)
O2—C8—C9—C12	−179.5 (3)	C3—C2—O1—C1	10.3 (5)
N1—C8—C9—C12	0.1 (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—C11	150.4 (3)	C9—C8—N1—C7	−179.9 (3)
O2—C8—C9—C10	33.5 (4)	C6—C7—N1—C8	23.1 (5)
N1—C8—C9—C10	−146.9 (3)	C2—C7—N1—C8	−159.8 (3)
C12—C9—C10—C11	107.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N2	0.86 (2)	1.94 (2)	2.670 (3)	142 (3)
O3—H3O···O2ⁱ	0.85 (4)	1.93 (2)	2.751 (3)	162 (4)

Symmetry code: (i) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₆N₂O₃
M_r	248.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	16.062 (6), 5.483 (2), 14.250 (6)
β (°)	100.055 (6)
V (Å³)	1235.7 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.41 × 0.29 × 0.20

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1999)
T_min, T_max	0.96, 0.99
No. of measured, independent and observed [I > 2σ(I)] reflections	6430, 2432, 1520
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.073, 0.170, 1.09
No. of reflections	2432
No. of parameters	169
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.20

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 1008), SHELXTL-Plus (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···N2	0.856 (17)	1.94 (2)	2.670 (3)	142 (3)
O3—H3O···O2ⁱ	0.85 (4)	1.93 (2)	2.751 (3)	162 (4)

Symmetry code: (i) x, −y+1/2, z+1/2.

Acknowledgements

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

References

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