1-Cyano-N-(2,4,5-trichloro-phen-yl)cyclo-propane-1-carboxamide.

In the title compound, C(11)H(7)Cl(3)N(3)O, the dihedral angle between the benzene and cyclo-propane rings is 85.8 (2)°. In the crystal, mol-ecules are linked by C-H⋯O inter-actions, 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 = 289.54

Triclinic,

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[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.107

S = 1.04

2130 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.22 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811026225/hb5931sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811026225/hb5931Isup3.cml

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

C11H7Cl3N2O	Z = 2
Mr = 289.54	F(000) = 292
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0581P)2 + 0.1114P] where P = (Fo2 + 2Fc2)/3
2130 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

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
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)

	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)

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)

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

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) .