N-(4-Chloro-phen-yl)ethanimidamide.

A twisted conformation is found in the title compound, C(8)H(9)ClN(2), with the ethanimidamide residue being twisted substantially to the benzene ring [dihedral angle = 66.54 (14)°]. The conformation about the C=N double bond [1.299 (3) Å] is Z. A two-dimensional array with a zigzag topology is formed in the crystal structure via N-H⋯N and N-H⋯Cl hydrogen-bonding inter-actions.

Related literature

For background to the synthesis of N-(p-chloro­phen­yl)acetamidine and related N-aryl­acetamidines used as reagents in the formation of anti-leishmanial compounds, see: Shearer et al. (1997 ▶); Rousselet et al. (1993 ▶); Patai (1975 ▶). For background to leismaniasis, see: Ouellette et al. (2004 ▶); Croft et al. (2006 ▶); Ferreira et al. (2007 ▶); World Health Organization (2010 ▶).

Experimental

Crystal data

C8H9ClN2

M = 168.62

Orthorhombic,

a = 9.6460 (9) Å

b = 9.0192 (4) Å

c = 19.3281 (5) Å

V = 1681.53 (18) Å3

Z = 8

Mo Kα radiation

μ = 0.39 mm−1

T = 120 K

0.35 × 0.20 × 0.10 mm

Data collection

Nonius KappaCCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.792, T max = 1.000

14006 measured reflections

1924 independent reflections

1185 reflections with I > 2σ(I)

R int = 0.081

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.150

S = 1.05

1924 reflections

107 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.33 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810011013/hg2664sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011013/hg2664Isup2.hkl

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

C8H9ClN2	F(000) = 704
Mr = 168.62	Dx = 1.332 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2182 reflections
a = 9.6460 (9) Å	θ = 2.9–27.5°
b = 9.0192 (4) Å	µ = 0.39 mm−1
c = 19.3281 (5) Å	T = 120 K
V = 1681.53 (18) Å3	Block, colourless
Z = 8	0.35 × 0.20 × 0.10 mm

Nonius KappaCCD area-detector diffractometer	1924 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	1185 reflections with I > 2σ(I)
10 cm confocal mirrors	Rint = 0.081
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 3.0°
φ and ω scans	h = −11→12
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −11→9
Tmin = 0.792, Tmax = 1.000	l = −25→21
14006 measured reflections

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.081P)2] where P = (Fo2 + 2Fc2)/3
1924 reflections	(Δ/σ)max = 0.001
107 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

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.

	x	y	z	Uiso*/Ueq
Cl1	0.43525 (8)	0.20450 (7)	0.43084 (3)	0.0430 (3)
N1	0.36389 (19)	0.4659 (2)	0.71058 (10)	0.0308 (5)
N2	0.1234 (2)	0.4244 (2)	0.70948 (11)	0.0305 (5)
H1N	0.044 (3)	0.438 (3)	0.7313 (13)	0.037*
H2N	0.124 (3)	0.379 (3)	0.6740 (14)	0.037*
C1	0.3774 (2)	0.4032 (3)	0.64327 (12)	0.0274 (6)
C2	0.4543 (2)	0.2746 (3)	0.63454 (14)	0.0316 (6)
H2	0.4938	0.2272	0.6738	0.038*
C3	0.4741 (3)	0.2144 (3)	0.56933 (13)	0.0317 (6)
H3	0.5266	0.1260	0.5638	0.038*
C4	0.4169 (2)	0.2837 (3)	0.51261 (13)	0.0286 (6)
C5	0.3428 (3)	0.4144 (3)	0.51965 (12)	0.0342 (6)
H5	0.3054	0.4627	0.4802	0.041*
C6	0.3243 (3)	0.4736 (3)	0.58491 (13)	0.0348 (6)
H6	0.2745	0.5638	0.5901	0.042*
C7	0.2408 (2)	0.4770 (3)	0.73731 (13)	0.0269 (6)
C8	0.2239 (3)	0.5538 (3)	0.80540 (14)	0.0367 (6)
H8A	0.3153	0.5706	0.8261	0.055*
H8B	0.1680	0.4919	0.8364	0.055*
H8C	0.1774	0.6492	0.7983	0.055*

	U11	U22	U33	U12	U13	U23
Cl1	0.0537 (5)	0.0446 (5)	0.0307 (4)	0.0051 (3)	0.0060 (3)	−0.0034 (3)
N1	0.0210 (11)	0.0449 (13)	0.0264 (12)	−0.0010 (9)	−0.0007 (9)	−0.0032 (9)
N2	0.0205 (11)	0.0461 (14)	0.0248 (12)	−0.0033 (9)	0.0019 (9)	−0.0061 (10)
C1	0.0171 (11)	0.0372 (14)	0.0280 (14)	−0.0036 (10)	−0.0002 (10)	0.0003 (11)
C2	0.0286 (13)	0.0340 (14)	0.0321 (15)	−0.0010 (11)	−0.0040 (11)	0.0052 (11)
C3	0.0297 (13)	0.0288 (13)	0.0367 (16)	0.0031 (10)	0.0014 (11)	0.0001 (11)
C4	0.0284 (13)	0.0306 (15)	0.0266 (14)	−0.0016 (10)	0.0072 (10)	0.0012 (10)
C5	0.0327 (14)	0.0437 (16)	0.0263 (14)	0.0074 (11)	0.0018 (11)	0.0068 (11)
C6	0.0296 (14)	0.0403 (15)	0.0345 (15)	0.0119 (11)	0.0047 (12)	0.0019 (11)
C7	0.0233 (12)	0.0329 (13)	0.0246 (14)	−0.0026 (10)	−0.0006 (10)	0.0029 (10)
C8	0.0281 (13)	0.0512 (16)	0.0307 (14)	−0.0059 (12)	0.0014 (11)	−0.0066 (12)

Cl1—C4	1.743 (3)	C3—C4	1.377 (4)
N1—C7	1.299 (3)	C3—H3	0.9500
N1—C1	1.425 (3)	C4—C5	1.385 (3)
N2—C7	1.340 (3)	C5—C6	1.381 (3)
N2—H1N	0.89 (3)	C5—H5	0.9500
N2—H2N	0.80 (3)	C6—H6	0.9500
C1—C2	1.387 (3)	C7—C8	1.496 (4)
C1—C6	1.393 (3)	C8—H8A	0.9800
C2—C3	1.386 (4)	C8—H8B	0.9800
C2—H2	0.9500	C8—H8C	0.9800
C7—N1—C1	118.52 (19)	C6—C5—C4	119.1 (2)
C7—N2—H1N	119.4 (17)	C6—C5—H5	120.5
C7—N2—H2N	121 (2)	C4—C5—H5	120.5
H1N—N2—H2N	119 (3)	C5—C6—C1	121.0 (2)
C2—C1—C6	118.7 (2)	C5—C6—H6	119.5
C2—C1—N1	119.5 (2)	C1—C6—H6	119.5
C6—C1—N1	121.6 (2)	N1—C7—N2	125.8 (2)
C3—C2—C1	120.8 (2)	N1—C7—C8	119.0 (2)
C3—C2—H2	119.6	N2—C7—C8	115.2 (2)
C1—C2—H2	119.6	C7—C8—H8A	109.5
C4—C3—C2	119.4 (2)	C7—C8—H8B	109.5
C4—C3—H3	120.3	H8A—C8—H8B	109.5
C2—C3—H3	120.3	C7—C8—H8C	109.5
C3—C4—C5	121.0 (2)	H8A—C8—H8C	109.5
C3—C4—Cl1	119.65 (19)	H8B—C8—H8C	109.5
C5—C4—Cl1	119.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1n···N1i	0.88 (3)	2.08 (3)	2.965 (3)	176 (3)
N2—H2n···Cl1ii	0.80 (3)	2.83 (3)	3.464 (2)	138 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1n⋯N1i	0.88 (3)	2.08 (3)	2.965 (3)	176 (3)
N2—H2n⋯Cl1ii	0.80 (3)	2.83 (3)	3.464 (2)	138 (3)

Symmetry codes: (i) ; (ii) .