(E)-3-Chloro-N'-hy-droxy-benzene-1-carboximidamide.

The title compound, C7H7ClN2O, crystallizes with two independent mol-ecules in the asymmetric unit. The compound adopts an E configuration across the C=N double bond, as the -OH group and the benzene ring are on opposite sides of the double bond while the H atom of the hy-droxy group is directed away from the -NH2 group. In the crystal, mol-ecules are linked to one another through O-H⋯N and N-H⋯O hydrogen bonds, forming chains along [010].

Related literature

For related syntheses and the biological activity of oxadiazo­les, see: Kundu et al. (2012 ▶); Sakamoto et al. (2007 ▶); Tyrkov & Sukhenko (2004 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C7H7ClN2O

M = 170.60

Triclinic,

a = 5.0018 (17) Å

b = 10.984 (4) Å

c = 14.407 (6) Å

α = 74.000 (12)°

β = 89.952 (12)°

γ = 89.877 (11)°

V = 760.9 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.44 mm−1

T = 298 K

0.24 × 0.22 × 0.20 mm

Data collection

Bruker SMART X2S diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.902, T max = 0.917

14972 measured reflections

2655 independent reflections

2192 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.109

S = 1.05

2655 reflections

218 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812046612/jj2159sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812046612/jj2159Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812046612/jj2159Isup3.cml

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

C7H7ClN2O	F(000) = 352
Mr = 170.60	Prism
Triclinic, P1	Dx = 1.489 Mg m−3
Hall symbol: -P 1	Melting point: 386 K
a = 5.0018 (17) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.984 (4) Å	Cell parameters from 218 reflections
c = 14.407 (6) Å	θ = 1.9–25°
α = 74.000 (12)°	µ = 0.44 mm−1
β = 89.952 (12)°	T = 298 K
γ = 89.877 (11)°	Prism, colourless
V = 760.9 (5) Å3	0.24 × 0.22 × 0.20 mm
Z = 4

Bruker SMART X2S diffractometer	2655 independent reflections
Radiation source: fine-focus sealed tube	2192 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.060
Detector resolution: 1.20 pixels mm-1	θmax = 25.0°, θmin = 1.9°
phi and ω scans	h = −5→5
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	k = −13→13
Tmin = 0.902, Tmax = 0.917	l = −17→17
14972 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.109	w = 1/[σ2(Fo2) + (0.0546P)2 + 0.1852P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
2655 reflections	Δρmax = 0.19 e Å−3
218 parameters	Δρmin = −0.24 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraints	Extinction coefficient: 0.024 (4)
Primary atom site location: structure-invariant direct methods

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
H1B	0.079 (5)	0.805 (3)	0.050 (2)	0.066 (8)*
H3B	0.430 (5)	0.301 (3)	0.047 (2)	0.065 (8)*
H3A	0.247 (5)	0.322 (2)	0.1254 (17)	0.043 (6)*
H1A	0.256 (5)	0.823 (2)	0.124 (2)	0.060 (7)*
Cl1	0.42873 (11)	0.85954 (5)	0.44393 (4)	0.0554 (2)
O1	−0.3214 (3)	0.87635 (13)	0.00143 (11)	0.0422 (4)
H1	−0.4285	0.9158	−0.0388	0.063*
N1	0.0928 (3)	0.81988 (15)	0.10588 (14)	0.0382 (4)
N2	−0.3071 (3)	0.93253 (14)	0.08000 (12)	0.0356 (4)
C1	−0.0344 (3)	0.95168 (15)	0.20990 (13)	0.0300 (4)
C2	0.1471 (3)	0.89050 (16)	0.28068 (14)	0.0345 (4)
H2	0.2326	0.8170	0.2763	0.041*
C3	0.1997 (4)	0.93902 (17)	0.35722 (14)	0.0363 (4)
C4	0.0746 (4)	1.04675 (18)	0.36709 (15)	0.0417 (5)
H4	0.1116	1.0783	0.4193	0.050*
C5	−0.1068 (4)	1.10622 (19)	0.29740 (16)	0.0456 (5)
H5	−0.1939	1.1787	0.3030	0.055*
C6	−0.1621 (4)	1.06053 (17)	0.21941 (15)	0.0398 (5)
H6	−0.2849	1.1024	0.1731	0.048*
C7	−0.0862 (3)	0.90061 (15)	0.12633 (13)	0.0285 (4)
Cl2	0.07127 (12)	0.35954 (5)	0.44389 (4)	0.0556 (2)
O2	0.8210 (3)	0.37629 (13)	0.00125 (11)	0.0420 (3)
H2A	0.9256	0.4165	−0.0396	0.063*
N3	0.4070 (4)	0.31958 (15)	0.10577 (14)	0.0381 (4)
N4	0.8071 (3)	0.43247 (15)	0.08013 (12)	0.0357 (4)
C8	0.5338 (3)	0.45141 (15)	0.20995 (13)	0.0298 (4)
C9	0.3535 (4)	0.39047 (16)	0.28028 (14)	0.0350 (4)
H9	0.2684	0.3172	0.2757	0.042*
C10	0.3003 (4)	0.43874 (17)	0.35716 (14)	0.0363 (4)
C11	0.4257 (4)	0.54666 (18)	0.36691 (15)	0.0422 (5)
H11	0.3885	0.5782	0.4192	0.051*
C12	0.6065 (4)	0.60617 (19)	0.29736 (16)	0.0457 (5)
H12	0.6931	0.6786	0.3030	0.055*
C13	0.6620 (4)	0.56053 (17)	0.21931 (15)	0.0396 (5)
H13	0.7845	0.6023	0.1729	0.048*
C14	0.5860 (3)	0.40097 (15)	0.12632 (13)	0.0286 (4)

	U11	U22	U33	U12	U13	U23
Cl1	0.0630 (4)	0.0547 (3)	0.0467 (4)	0.0016 (2)	−0.0246 (3)	−0.0106 (2)
O1	0.0441 (8)	0.0484 (8)	0.0418 (8)	0.0024 (6)	−0.0111 (6)	−0.0251 (7)
N1	0.0349 (10)	0.0440 (9)	0.0412 (10)	0.0039 (7)	−0.0025 (7)	−0.0210 (8)
N2	0.0357 (9)	0.0405 (8)	0.0357 (9)	0.0016 (6)	−0.0075 (7)	−0.0191 (7)
C1	0.0289 (9)	0.0297 (8)	0.0321 (10)	−0.0037 (6)	−0.0001 (7)	−0.0097 (7)
C2	0.0353 (10)	0.0311 (9)	0.0383 (11)	0.0006 (7)	−0.0048 (8)	−0.0114 (8)
C3	0.0358 (10)	0.0381 (9)	0.0335 (10)	−0.0059 (7)	−0.0049 (8)	−0.0075 (8)
C4	0.0522 (12)	0.0401 (10)	0.0375 (11)	−0.0075 (8)	−0.0013 (9)	−0.0185 (9)
C5	0.0544 (13)	0.0391 (10)	0.0500 (13)	0.0068 (8)	−0.0044 (10)	−0.0233 (9)
C6	0.0418 (11)	0.0377 (10)	0.0417 (11)	0.0078 (8)	−0.0107 (8)	−0.0138 (8)
C7	0.0284 (9)	0.0263 (8)	0.0308 (9)	−0.0042 (6)	0.0003 (7)	−0.0081 (7)
Cl2	0.0633 (4)	0.0552 (3)	0.0465 (4)	−0.0023 (2)	0.0241 (3)	−0.0109 (2)
O2	0.0445 (8)	0.0488 (8)	0.0404 (8)	−0.0033 (6)	0.0107 (6)	−0.0252 (7)
N3	0.0331 (10)	0.0442 (9)	0.0423 (10)	−0.0049 (7)	0.0039 (7)	−0.0211 (8)
N4	0.0347 (9)	0.0411 (8)	0.0367 (9)	−0.0018 (6)	0.0056 (7)	−0.0197 (7)
C8	0.0290 (9)	0.0296 (8)	0.0320 (10)	0.0029 (6)	0.0001 (7)	−0.0103 (7)
C9	0.0351 (10)	0.0313 (9)	0.0401 (11)	−0.0006 (7)	0.0044 (8)	−0.0122 (8)
C10	0.0374 (11)	0.0366 (9)	0.0334 (10)	0.0054 (7)	0.0049 (8)	−0.0074 (8)
C11	0.0538 (13)	0.0404 (10)	0.0366 (11)	0.0076 (8)	0.0004 (9)	−0.0181 (9)
C12	0.0545 (13)	0.0390 (10)	0.0497 (13)	−0.0072 (9)	0.0040 (10)	−0.0225 (9)
C13	0.0423 (11)	0.0373 (10)	0.0420 (12)	−0.0085 (8)	0.0083 (8)	−0.0154 (8)
C14	0.0273 (9)	0.0274 (8)	0.0311 (9)	0.0035 (6)	−0.0005 (7)	−0.0081 (7)

Cl1—C3	1.7412 (19)	Cl2—C10	1.742 (2)
O1—N2	1.433 (2)	O2—N4	1.436 (2)
O1—H1	0.8200	O2—H2A	0.8200
N1—C7	1.347 (2)	N3—C14	1.356 (2)
N1—H1B	0.87 (3)	N3—H3B	0.92 (3)
N1—H1A	0.86 (3)	N3—H3A	0.85 (2)
N2—C7	1.288 (2)	N4—C14	1.288 (2)
C1—C2	1.391 (2)	C8—C9	1.384 (3)
C1—C6	1.394 (3)	C8—C13	1.399 (2)
C1—C7	1.485 (2)	C8—C14	1.481 (2)
C2—C3	1.376 (3)	C9—C10	1.379 (3)
C2—H2	0.9300	C9—H9	0.9300
C3—C4	1.379 (3)	C10—C11	1.383 (3)
C4—C5	1.377 (3)	C11—C12	1.375 (3)
C4—H4	0.9300	C11—H11	0.9300
C5—C6	1.380 (3)	C12—C13	1.379 (3)
C5—H5	0.9300	C12—H12	0.9300
C6—H6	0.9300	C13—H13	0.9300
N2—O1—H1	109.5	N4—O2—H2A	109.5
C7—N1—H1B	116.7 (17)	C14—N3—H3B	116.1 (16)
C7—N1—H1A	118.6 (17)	C14—N3—H3A	117.6 (15)
H1B—N1—H1A	114 (2)	H3B—N3—H3A	117 (2)
C7—N2—O1	109.78 (14)	C14—N4—O2	109.65 (14)
C2—C1—C6	118.65 (17)	C9—C8—C13	118.93 (17)
C2—C1—C7	119.67 (15)	C9—C8—C14	119.71 (15)
C6—C1—C7	121.67 (16)	C13—C8—C14	121.36 (16)
C3—C2—C1	119.83 (17)	C10—C9—C8	119.82 (16)
C3—C2—H2	120.1	C10—C9—H9	120.1
C1—C2—H2	120.1	C8—C9—H9	120.1
C2—C3—C4	121.88 (17)	C9—C10—C11	121.64 (18)
C2—C3—Cl1	118.24 (14)	C9—C10—Cl2	118.40 (14)
C4—C3—Cl1	119.87 (15)	C11—C10—Cl2	119.96 (15)
C5—C4—C3	118.08 (18)	C12—C11—C10	118.32 (18)
C5—C4—H4	121.0	C12—C11—H11	120.8
C3—C4—H4	121.0	C10—C11—H11	120.8
C4—C5—C6	121.40 (18)	C11—C12—C13	121.28 (18)
C4—C5—H5	119.3	C11—C12—H12	119.4
C6—C5—H5	119.3	C13—C12—H12	119.4
C5—C6—C1	120.15 (18)	C12—C13—C8	120.01 (18)
C5—C6—H6	119.9	C12—C13—H13	120.0
C1—C6—H6	119.9	C8—C13—H13	120.0
N2—C7—N1	123.84 (17)	N4—C14—N3	123.71 (17)
N2—C7—C1	117.48 (15)	N4—C14—C8	117.58 (15)
N1—C7—C1	118.61 (16)	N3—C14—C8	118.62 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N4i	0.82	2.09	2.811 (2)	147
N3—H3B···O1ii	0.92 (3)	2.32 (3)	3.006 (2)	131 (2)
O1—H1···N2iii	0.82	2.08	2.805 (2)	147
N1—H1B···O2iv	0.87 (3)	2.36 (3)	3.006 (3)	132 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯N4i	0.82	2.09	2.811 (2)	147
N3—H3B⋯O1ii	0.92 (3)	2.32 (3)	3.006 (2)	131 (2)
O1—H1⋯N2iii	0.82	2.08	2.805 (2)	147
N1—H1B⋯O2iv	0.87 (3)	2.36 (3)	3.006 (3)	132 (3)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .