1-Cyano-N-(2,4,5-trichloro­phen­yl)cyclo­propane-1-carboxamide

Liu, H.-J.; Weng, J.-Q.; Tan, C.-X.; Liu, X.-H.

doi:10.1107/S1600536811026225

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o1940

doi:10.1107/S1600536811026225

Open

access

1-Cyano-N-(2,4,5-trichlorophenyl)cyclopropane-1-carboxamide

Hui-Jun Liu,^a Jian-Quan Weng,^a Cheng-Xia Tan ^a and Xing-Hai Liu ^a ^*

^aCollege of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
^*Correspondence e-mail: xhliu@zjut.edu.cn

(Received 23 June 2011; accepted 1 July 2011; online 6 July 2011)

In the title compound, C₁₁H₇Cl₃N₃O, the dihedral angle between the benzene and cyclopropane rings is 85.8 (2)°. In the crystal, molecules are linked by C—H⋯O interactions, generating C(5) chains propagating in the a-axis direction.

Related literature

For the synthesis, see: Liu et al. (2007 ). For the biological activity of related compounds, see: Liu et al. (2009 ).

Experimental

Crystal data

C₁₁H₇Cl₃N₂O
M_r = 289.54
Triclinic, $[P \overline 1]$
a = 6.0068 (18) Å
b = 7.420 (2) Å
c = 14.047 (4) Å
α = 77.531 (5)°
β = 86.958 (5)°
γ = 84.483 (5)°
V = 608.1 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.74 mm⁻¹
T = 294 K
0.24 × 0.22 × 0.18 mm

Data collection

Rigaku Mercury CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ) T_min = 0.614, T_max = 1.000
3103 measured reflections
2130 independent reflections
1619 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.107
S = 1.04
2130 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10B⋯O1ⁱ	0.97	2.56	3.439 (3)	151
Symmetry code: (i) x+1, y, z.

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811026225/hb5931sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811026225/hb5931Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811026225/hb5931Isup3.cml

checkCIF report

Comment top

Many cyclopropane compound exhibit good biological activity such as KARI (Liu et al., 2007; Liu et al., 2009). In continuation of this work, the title compound, (I), a 1-cyano-carboxamide derivatives had been synthesized. The strucuture was confirmed by X-ray crstallography.

Single-crystal X-ray diffraction analysis reveals that the title compound crystallizes in the triclinic space group P1 (Fig. 1). As shown in Fig. 2, the crystal structure is stabilized by weak C-H···O intermolecular interactions.

Related literature top

For the synthesis, see: Liu et al. (2007). For the biological activity of related compounds, see: Liu et al. (2009).

Experimental top

The title compound was prepared according to the literature procedures (Liu et al., 2007). Colourless prisms of (I) were grown from slow evaporation of ethanol solution at room temperature.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radius.
	Fig. 2. The crystal packing for (I).

1-Cyano-N-(2,4,5-trichlorophenyl)cyclopropane-1-carboxamide top

Crystal data top

C₁₁H₇Cl₃N₂O	Z = 2
M_r = 289.54	F(000) = 292
Triclinic, P1	D_x = 1.581 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.0068 (18) Å	Cell parameters from 1405 reflections
b = 7.420 (2) Å	θ = 3.0–26.2°
c = 14.047 (4) Å	µ = 0.74 mm⁻¹
α = 77.531 (5)°	T = 294 K
β = 86.958 (5)°	Prism, colorless
γ = 84.483 (5)°	0.24 × 0.22 × 0.18 mm
V = 608.1 (3) Å³

Data collection top

Rigaku Mercury CCD diffractometer	2130 independent reflections
Radiation source: fine-focus sealed tube	1619 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
phi and ω scans	θ_max = 25.0°, θ_min = 1.5°
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	h = −6→7
T_min = 0.614, T_max = 1.000	k = −8→7
3103 measured reflections	l = −16→16

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0581P)² + 0.1114P] where P = (F_o² + 2F_c²)/3
2130 reflections	(Δ/σ)_max < 0.001
154 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₁H₇Cl₃N₂O	γ = 84.483 (5)°
M_r = 289.54	V = 608.1 (3) Å³
Triclinic, P1	Z = 2
a = 6.0068 (18) Å	Mo Kα radiation
b = 7.420 (2) Å	µ = 0.74 mm⁻¹
c = 14.047 (4) Å	T = 294 K
α = 77.531 (5)°	0.24 × 0.22 × 0.18 mm
β = 86.958 (5)°

Data collection top

Rigaku Mercury CCD diffractometer	2130 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	1619 reflections with I > 2σ(I)
T_min = 0.614, T_max = 1.000	R_int = 0.025
3103 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 1.04	Δρ_max = 0.23 e Å⁻³
2130 reflections	Δρ_min = −0.22 e Å⁻³
154 parameters

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

	x	y	z	U_iso*/U_eq
Cl1	0.32398 (14)	0.92602 (9)	0.72571 (5)	0.0647 (3)
Cl2	−0.33513 (13)	0.75928 (12)	0.52559 (6)	0.0763 (3)
Cl3	−0.21699 (12)	0.33282 (11)	0.61532 (6)	0.0662 (3)
O1	0.4025 (3)	0.2145 (2)	0.84621 (14)	0.0576 (5)
N1	0.4219 (3)	0.5242 (2)	0.79194 (14)	0.0414 (5)
H1	0.4980	0.6139	0.7971	0.050*
N2	0.8457 (4)	0.6623 (3)	0.90380 (19)	0.0669 (7)
C1	0.1788 (4)	0.7600 (3)	0.69152 (17)	0.0445 (6)
C2	0.0042 (4)	0.8156 (4)	0.62960 (17)	0.0511 (6)
H2	−0.0315	0.9410	0.6044	0.061*
C3	−0.1181 (4)	0.6857 (4)	0.60479 (17)	0.0487 (6)
C4	−0.0613 (4)	0.4991 (4)	0.64223 (17)	0.0456 (6)
C5	0.1165 (4)	0.4420 (3)	0.70298 (17)	0.0416 (6)
H5	0.1535	0.3162	0.7265	0.050*
C6	0.2406 (4)	0.5713 (3)	0.72921 (16)	0.0384 (5)
C7	0.4916 (4)	0.3549 (3)	0.84540 (16)	0.0389 (5)
C8	0.6910 (4)	0.3493 (3)	0.90622 (17)	0.0399 (5)
C9	0.7029 (4)	0.2025 (4)	1.00043 (19)	0.0541 (7)
H9A	0.7702	0.2326	1.0557	0.065*
H9B	0.5788	0.1257	1.0172	0.065*
C10	0.8503 (4)	0.1735 (3)	0.9183 (2)	0.0542 (7)
H10A	0.8171	0.0790	0.8844	0.065*
H10B	1.0084	0.1859	0.9229	0.065*
C11	0.7815 (4)	0.5227 (3)	0.90572 (18)	0.0448 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0982 (6)	0.0340 (4)	0.0636 (4)	−0.0070 (3)	−0.0273 (4)	−0.0075 (3)
Cl2	0.0624 (5)	0.0970 (6)	0.0646 (5)	0.0174 (4)	−0.0291 (4)	−0.0110 (4)
Cl3	0.0541 (4)	0.0776 (5)	0.0773 (5)	−0.0072 (3)	−0.0193 (3)	−0.0347 (4)
O1	0.0623 (12)	0.0366 (10)	0.0747 (12)	−0.0121 (8)	−0.0290 (9)	−0.0040 (9)
N1	0.0473 (11)	0.0293 (10)	0.0494 (11)	−0.0057 (8)	−0.0149 (9)	−0.0083 (9)
N2	0.0657 (15)	0.0534 (15)	0.0857 (18)	−0.0150 (12)	−0.0214 (13)	−0.0152 (13)
C1	0.0563 (15)	0.0387 (13)	0.0391 (13)	−0.0025 (11)	−0.0064 (11)	−0.0093 (10)
C2	0.0622 (17)	0.0453 (15)	0.0418 (14)	0.0097 (12)	−0.0073 (12)	−0.0054 (12)
C3	0.0449 (14)	0.0644 (17)	0.0354 (13)	0.0079 (12)	−0.0098 (10)	−0.0111 (12)
C4	0.0426 (14)	0.0563 (15)	0.0419 (13)	−0.0019 (11)	−0.0058 (11)	−0.0193 (12)
C5	0.0447 (14)	0.0379 (13)	0.0445 (13)	0.0014 (10)	−0.0099 (11)	−0.0137 (11)
C6	0.0420 (13)	0.0376 (13)	0.0364 (12)	0.0018 (10)	−0.0060 (10)	−0.0107 (10)
C7	0.0384 (13)	0.0365 (13)	0.0429 (13)	−0.0024 (10)	−0.0065 (10)	−0.0095 (10)
C8	0.0366 (13)	0.0361 (12)	0.0470 (14)	−0.0044 (10)	−0.0061 (10)	−0.0070 (10)
C9	0.0567 (16)	0.0532 (16)	0.0497 (15)	−0.0139 (12)	−0.0155 (13)	0.0026 (12)
C10	0.0459 (15)	0.0420 (14)	0.0719 (18)	0.0037 (11)	−0.0141 (13)	−0.0063 (13)
C11	0.0405 (13)	0.0430 (14)	0.0517 (14)	−0.0039 (11)	−0.0124 (11)	−0.0090 (11)

Geometric parameters (Å, º) top

Cl1—C1	1.736 (2)	C4—C5	1.379 (3)
Cl2—C3	1.729 (2)	C5—C6	1.390 (3)
Cl3—C4	1.732 (2)	C5—H5	0.9300
O1—C7	1.213 (3)	C7—C8	1.500 (3)
N1—C7	1.357 (3)	C8—C11	1.442 (3)
N1—C6	1.407 (3)	C8—C9	1.522 (3)
N1—H1	0.8600	C8—C10	1.525 (3)
N2—C11	1.134 (3)	C9—C10	1.456 (4)
C1—C2	1.373 (3)	C9—H9A	0.9700
C1—C6	1.407 (3)	C9—H9B	0.9700
C2—C3	1.378 (4)	C10—H10A	0.9700
C2—H2	0.9300	C10—H10B	0.9700
C3—C4	1.386 (4)

C7—N1—C6	128.11 (18)	O1—C7—C8	120.4 (2)
C7—N1—H1	115.9	N1—C7—C8	115.52 (18)
C6—N1—H1	115.9	C11—C8—C7	117.5 (2)
C2—C1—C6	121.4 (2)	C11—C8—C9	117.5 (2)
C2—C1—Cl1	119.39 (19)	C7—C8—C9	116.26 (19)
C6—C1—Cl1	119.17 (18)	C11—C8—C10	118.7 (2)
C1—C2—C3	120.1 (2)	C7—C8—C10	116.0 (2)
C1—C2—H2	120.0	C9—C8—C10	57.10 (17)
C3—C2—H2	120.0	C10—C9—C8	61.57 (16)
C2—C3—C4	119.2 (2)	C10—C9—H9A	117.6
C2—C3—Cl2	119.1 (2)	C8—C9—H9A	117.6
C4—C3—Cl2	121.6 (2)	C10—C9—H9B	117.6
C5—C4—C3	121.1 (2)	C8—C9—H9B	117.6
C5—C4—Cl3	118.6 (2)	H9A—C9—H9B	114.7
C3—C4—Cl3	120.33 (19)	C9—C10—C8	61.33 (17)
C4—C5—C6	120.4 (2)	C9—C10—H10A	117.6
C4—C5—H5	119.8	C8—C10—H10A	117.6
C6—C5—H5	119.8	C9—C10—H10B	117.6
C5—C6—C1	117.8 (2)	C8—C10—H10B	117.6
C5—C6—N1	123.8 (2)	H10A—C10—H10B	114.7
C1—C6—N1	118.4 (2)	N2—C11—C8	177.5 (3)
O1—C7—N1	124.1 (2)

C6—C1—C2—C3	1.5 (4)	C7—N1—C6—C1	171.1 (2)
Cl1—C1—C2—C3	−177.48 (19)	C6—N1—C7—O1	0.1 (4)
C1—C2—C3—C4	−0.7 (4)	C6—N1—C7—C8	−179.6 (2)
C1—C2—C3—Cl2	−179.28 (19)	O1—C7—C8—C11	−176.9 (2)
C2—C3—C4—C5	−0.6 (4)	N1—C7—C8—C11	2.9 (3)
Cl2—C3—C4—C5	178.01 (18)	O1—C7—C8—C9	−30.1 (3)
C2—C3—C4—Cl3	178.07 (18)	N1—C7—C8—C9	149.7 (2)
Cl2—C3—C4—Cl3	−3.4 (3)	O1—C7—C8—C10	34.3 (3)
C3—C4—C5—C6	1.0 (4)	N1—C7—C8—C10	−146.0 (2)
Cl3—C4—C5—C6	−177.66 (18)	C11—C8—C9—C10	−107.9 (2)
C4—C5—C6—C1	−0.2 (3)	C7—C8—C9—C10	105.3 (2)
C4—C5—C6—N1	179.0 (2)	C11—C8—C10—C9	105.8 (2)
C2—C1—C6—C5	−1.0 (3)	C7—C8—C10—C9	−105.7 (2)
Cl1—C1—C6—C5	177.93 (17)	C7—C8—C11—N2	14 (7)
C2—C1—C6—N1	179.7 (2)	C9—C8—C11—N2	−132 (7)
Cl1—C1—C6—N1	−1.3 (3)	C10—C8—C11—N2	162 (6)
C7—N1—C6—C5	−8.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···O1ⁱ	0.97	2.56	3.439 (3)	151

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₁H₇Cl₃N₂O
M_r	289.54
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	6.0068 (18), 7.420 (2), 14.047 (4)
α, β, γ (°)	77.531 (5), 86.958 (5), 84.483 (5)
V (Å³)	608.1 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.74
Crystal size (mm)	0.24 × 0.22 × 0.18

Data collection
Diffractometer	Rigaku Mercury CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku/MSC, 2005)
T_min, T_max	0.614, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	3103, 2130, 1619
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.107, 1.04
No. of reflections	2130
No. of parameters	154
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.22

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···O1ⁱ	0.97	2.56	3.439 (3)	151

Symmetry code: (i) x+1, y, z.

Acknowledgements

This work was supported financially by the National Natural Science Foundation of China (Nos. 21002090, 31000008, 30900959), the Key Laboratory of Pesticide Chemistry and Applications, Ministry of Agriculture (MOA), Beijing 100193, People's Republic of China (No. MOAPCA201005) and the Scientific Research Fund of Zhejiang Education Department (Y201018479).

References

Liu, X. H., Chen, P. Q., Wang, B. L., Li, Y. H., Wang, S. H. & Li, Z. M. (2007). Bioorg. Med. Chem. Lett. 17, 3784–3788. Web of Science CSD CrossRef PubMed CAS Google Scholar
Liu, X. H., Shi, Y. X., Ma, Y., Zhang, C. Y., Dong, W. L., Li, P., Wang, B. L., li, B. J. & li, Z. M. (2009). Eur. J. Med. Chem. 44, 2782–2786. Web of Science CrossRef PubMed CAS Google Scholar
Rigaku/MSC (2005). CrystalClear. Rigaku/MSC Inc. The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar