3-Chloro-benzohydrazide.

In the title compound, C(7)H(7)ClN(2)O, the hydrazide group is inclined at a dihedral angle of 32.30 (11)° with respect to the benzene ring. The amino H atoms form inter-molecular N-H⋯O hydrogen bonds with the O atoms of two adjacent mol-ecules, resulting in 10-membered rings of graph-set motif R(2) (2)(10). The imino H atom is also involved in an inter-molecular hydrogen bond with an amino N atom of a symmetry-related mol-ecule, resulting in a zigzag chain along the b axis. The structure is further consolidated by an intra-molecular N-H⋯O inter-action, which results in a five-membered ring.

Related literature

For the biological activity of hydrazides, see: Ashiq, Ara et al. (2008 ▶); Ara et al. (2007 ▶); Maqsood et al. (2006 ▶); For related structures, see: Ashiq, Jamal et al. (2008 ▶); Jamal et al. (2008 ▶, 2009 ▶); Kallel et al. (1992 ▶); Ratajczak et al. (2001 ▶); Saraogi et al. (2002 ▶). For graph-set notation of hydrogen-bond motifs, see: (Bernstein et al. 1995 ▶).

Experimental

Crystal data

C7H7ClN2O

M = 170.60

Monoclinic,

a = 16.2005 (15) Å

b = 3.8165 (4) Å

c = 12.7646 (13) Å

β = 108.030 (5)°

V = 750.47 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.45 mm−1

T = 296 K

0.43 × 0.21 × 0.17 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.832, T max = 0.928

8144 measured reflections

1881 independent reflections

1101 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.121

S = 1.01

1880 reflections

109 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810029508/pv2308sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029508/pv2308Isup2.hkl

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

C7H7ClN2O	F(000) = 352
Mr = 170.60	Dx = 1.510 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1323 reflections
a = 16.2005 (15) Å	θ = 3.2–23.3°
b = 3.8165 (4) Å	µ = 0.45 mm−1
c = 12.7646 (13) Å	T = 296 K
β = 108.030 (5)°	Needle, colorless
V = 750.47 (13) Å3	0.43 × 0.21 × 0.17 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	1881 independent reflections
Radiation source: fine-focus sealed tube	1101 reflections with I > 2σ(I)
graphite	Rint = 0.053
ω scans	θmax = 28.5°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −21→21
Tmin = 0.832, Tmax = 0.928	k = −5→5
8144 measured reflections	l = −17→17

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0424P)2 + 0.4337P] where P = (Fo2 + 2Fc2)/3
1880 reflections	(Δ/σ)max < 0.001
109 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

Experimental. the reflection 1 0 0 has been obscured by the beam stop so it was omitted in the final refinement

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	0.43417 (4)	1.3067 (2)	0.63671 (7)	0.0544 (3)
O1	0.11735 (11)	0.7193 (5)	0.53677 (14)	0.0392 (5)
N1	0.05596 (12)	0.8834 (6)	0.36054 (17)	0.0336 (5)
H1N	0.0600 (15)	0.987 (8)	0.301 (2)	0.040*
N2	−0.02733 (13)	0.7486 (7)	0.35190 (18)	0.0352 (6)
H3N	−0.0560 (16)	0.902 (8)	0.376 (2)	0.042*
H2N	−0.0219 (16)	0.571 (8)	0.399 (2)	0.042*
C1	0.20977 (14)	0.9403 (7)	0.43785 (19)	0.0295 (6)
C2	0.27380 (15)	1.0618 (7)	0.5299 (2)	0.0331 (6)
H2	0.2629	1.0822	0.5971	0.040*
C3	0.35388 (15)	1.1523 (7)	0.5212 (2)	0.0365 (6)
C4	0.37114 (17)	1.1191 (8)	0.4231 (2)	0.0445 (7)
H4	0.4252	1.1827	0.4180	0.053*
C5	0.30846 (17)	0.9917 (9)	0.3325 (2)	0.0472 (8)
H5	0.3205	0.9645	0.2663	0.057*
C6	0.22744 (16)	0.9033 (8)	0.3388 (2)	0.0380 (7)
H6	0.1849	0.8194	0.2768	0.046*
C7	0.12403 (15)	0.8398 (7)	0.45054 (19)	0.0286 (5)

	U11	U22	U33	U12	U13	U23
Cl1	0.0334 (3)	0.0599 (5)	0.0633 (5)	−0.0054 (3)	0.0055 (3)	−0.0109 (4)
O1	0.0392 (9)	0.0492 (13)	0.0309 (9)	−0.0036 (9)	0.0133 (7)	0.0086 (9)
N1	0.0321 (11)	0.0414 (15)	0.0281 (11)	−0.0062 (10)	0.0106 (9)	0.0069 (10)
N2	0.0312 (11)	0.0440 (17)	0.0331 (12)	−0.0057 (10)	0.0138 (9)	−0.0015 (11)
C1	0.0310 (12)	0.0254 (14)	0.0336 (13)	0.0014 (10)	0.0120 (10)	0.0031 (11)
C2	0.0338 (12)	0.0323 (16)	0.0351 (14)	−0.0003 (11)	0.0131 (11)	0.0021 (12)
C3	0.0305 (12)	0.0293 (16)	0.0469 (16)	0.0012 (11)	0.0081 (11)	0.0013 (13)
C4	0.0319 (13)	0.0456 (19)	0.0609 (19)	0.0030 (13)	0.0216 (13)	0.0055 (15)
C5	0.0458 (16)	0.058 (2)	0.0472 (17)	0.0028 (15)	0.0282 (13)	0.0043 (16)
C6	0.0369 (13)	0.0451 (19)	0.0340 (14)	−0.0006 (13)	0.0138 (11)	−0.0019 (13)
C7	0.0342 (12)	0.0253 (14)	0.0288 (12)	−0.0008 (11)	0.0132 (10)	−0.0018 (11)

Cl1—C3	1.740 (3)	C1—C7	1.497 (3)
O1—C7	1.228 (3)	C2—C3	1.380 (3)
N1—C7	1.334 (3)	C2—H2	0.9300
N1—N2	1.416 (3)	C3—C4	1.371 (4)
N1—H1N	0.87 (3)	C4—C5	1.370 (4)
N2—H3N	0.86 (3)	C4—H4	0.9300
N2—H2N	0.90 (3)	C5—C6	1.381 (3)
C1—C2	1.385 (3)	C5—H5	0.9300
C1—C6	1.387 (3)	C6—H6	0.9300
C7—N1—N2	122.4 (2)	C2—C3—Cl1	119.4 (2)
C7—N1—H1N	122.6 (16)	C3—C4—C5	119.7 (2)
N2—N1—H1N	114.9 (16)	C3—C4—H4	120.1
N1—N2—H3N	109.4 (19)	C5—C4—H4	120.1
N1—N2—H2N	109.3 (16)	C4—C5—C6	120.5 (3)
H3N—N2—H2N	103 (3)	C4—C5—H5	119.8
C2—C1—C6	119.7 (2)	C6—C5—H5	119.8
C2—C1—C7	118.0 (2)	C5—C6—C1	119.7 (2)
C6—C1—C7	122.2 (2)	C5—C6—H6	120.1
C3—C2—C1	119.4 (2)	C1—C6—H6	120.1
C3—C2—H2	120.3	O1—C7—N1	122.7 (2)
C1—C2—H2	120.3	O1—C7—C1	122.3 (2)
C4—C3—C2	120.9 (2)	N1—C7—C1	115.0 (2)
C4—C3—Cl1	119.7 (2)
C6—C1—C2—C3	1.5 (4)	C2—C1—C6—C5	−0.7 (4)
C7—C1—C2—C3	179.2 (2)	C7—C1—C6—C5	−178.3 (3)
C1—C2—C3—C4	−0.9 (4)	N2—N1—C7—O1	−9.3 (4)
C1—C2—C3—Cl1	179.7 (2)	N2—N1—C7—C1	169.2 (2)
C2—C3—C4—C5	−0.5 (4)	C2—C1—C7—O1	−31.5 (4)
Cl1—C3—C4—C5	178.9 (2)	C6—C1—C7—O1	146.2 (3)
C3—C4—C5—C6	1.3 (5)	C2—C1—C7—N1	150.0 (2)
C4—C5—C6—C1	−0.7 (5)	C6—C1—C7—N1	−32.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1	0.90 (3)	2.45 (3)	2.766 (3)	101 (2)
N1—H1N···N2i	0.87 (3)	2.11 (3)	2.955 (3)	162 (2)
N2—H3N···O1ii	0.86 (3)	2.24 (3)	3.091 (3)	171 (2)
N2—H2N···O1iii	0.90 (3)	2.25 (3)	2.935 (3)	133 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O1	0.90 (3)	2.45 (3)	2.766 (3)	101 (2)
N1—H1N⋯N2i	0.87 (3)	2.11 (3)	2.955 (3)	162 (2)
N2—H3N⋯O1ii	0.86 (3)	2.24 (3)	3.091 (3)	171 (2)
N2—H2N⋯O1iii	0.90 (3)	2.25 (3)	2.935 (3)	133 (2)

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