2-Chloro-benzohydrazide.

The asymmetric unit of the the title compound, C(7)H(7)ClN(2)O, contains two mol-ecules in which the chloro-phenyl and the formic hydrazide units are almost planar (r.m.s. deviations of 0.0081 and 0.0100 Å, respectively, in one mol-ecule and 0.0069 and 0.0150 Å in the other) and are oriented with respect to each other at dihedral angles of 56.8 (2) and 56.9 (2)°. In the crystal, the mol-ecules are consolidated in the form of polymeric chains extending along [010]. R(3) (3)(10) ring motifs exist due to N-H⋯O and N-H⋯N hydrogen bonds.

Related literature

For a related structure, see: Zareef et al. (2006 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶). For the synthetic method, see: Moise et al. (2009 ▶).

Experimental

Crystal data

C7H7ClN2O

M = 170.60

Monoclinic,

a = 25.7589 (16) Å

b = 4.9618 (3) Å

c = 12.9205 (8) Å

β = 103.648 (3)°

V = 1604.75 (17) Å3

Z = 8

Mo Kα radiation

μ = 0.42 mm−1

T = 296 K

0.34 × 0.14 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.979, T max = 0.988

11488 measured reflections

3091 independent reflections

2089 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.083

wR(F 2) = 0.217

S = 1.08

3091 reflections

211 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.80 e Å−3

Δρmin = −0.47 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812012640/ez2284sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812012640/ez2284Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812012640/ez2284Isup3.cml

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

C7H7ClN2O	F(000) = 704
Mr = 170.60	Dx = 1.412 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2089 reflections
a = 25.7589 (16) Å	θ = 0.8–26.0°
b = 4.9618 (3) Å	µ = 0.42 mm−1
c = 12.9205 (8) Å	T = 296 K
β = 103.648 (3)°	Needle, colorless
V = 1604.75 (17) Å3	0.34 × 0.14 × 0.12 mm
Z = 8

Bruker Kappa APEXII CCD diffractometer	3091 independent reflections
Radiation source: fine-focus sealed tube	2089 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
Detector resolution: 7.6 pixels mm-1	θmax = 26.0°, θmin = 0.8°
ω scans	h = −31→31
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −6→5
Tmin = 0.979, Tmax = 0.988	l = −15→15
11488 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)] = 0.083	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.217	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0577P)2 + 4.8436P] where P = (Fo2 + 2Fc2)/3
3091 reflections	(Δ/σ)max < 0.001
211 parameters	Δρmax = 0.80 e Å−3
0 restraints	Δρmin = −0.47 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.32498 (8)	−0.2330 (4)	0.33851 (15)	0.1011 (8)
O1	0.45056 (16)	−0.1875 (7)	0.4080 (3)	0.0622 (15)
N1	0.45512 (15)	0.2531 (8)	0.3704 (3)	0.0425 (12)
N2	0.49903 (18)	0.2265 (9)	0.3247 (4)	0.0481 (16)
C1	0.39139 (18)	0.1163 (10)	0.4673 (4)	0.0432 (17)
C2	0.3415 (2)	0.0002 (13)	0.4426 (4)	0.067 (2)
C3	0.3025 (3)	0.0750 (18)	0.4998 (7)	0.093 (3)
C4	0.3167 (3)	0.256 (2)	0.5818 (7)	0.102 (4)
C5	0.3654 (3)	0.3692 (15)	0.6064 (5)	0.080 (3)
C6	0.4023 (2)	0.3033 (11)	0.5501 (4)	0.0570 (17)
C7	0.43389 (18)	0.0452 (9)	0.4120 (3)	0.0397 (16)
Cl2	0.16784 (6)	0.7856 (3)	−0.01597 (14)	0.0751 (6)
O2	0.04466 (14)	0.6942 (7)	−0.0529 (3)	0.0583 (11)
N3	0.04524 (14)	0.2531 (7)	−0.0886 (3)	0.0399 (12)
N4	−0.00065 (18)	0.2615 (9)	−0.1749 (3)	0.0461 (14)
C8	0.10837 (18)	0.4182 (10)	0.0635 (3)	0.0422 (16)
C9	0.15626 (19)	0.5612 (12)	0.0799 (4)	0.0546 (19)
C10	0.1956 (2)	0.5229 (16)	0.1706 (6)	0.081 (3)
C11	0.1879 (3)	0.348 (2)	0.2458 (6)	0.094 (3)
C12	0.1414 (3)	0.2024 (17)	0.2324 (5)	0.089 (3)
C13	0.1015 (2)	0.2401 (12)	0.1409 (4)	0.0598 (19)
C14	0.06346 (18)	0.4680 (9)	−0.0317 (3)	0.0388 (16)
H1	0.44118	0.41011	0.37190	0.0512*
H2A	0.496 (2)	0.082 (12)	0.283 (4)	0.0577*
H2B	0.523 (2)	0.180 (13)	0.366 (4)	0.0577*
H3	0.26820	0.00263	0.48178	0.1112*
H4	0.29213	0.30088	0.62131	0.1223*
H5	0.37401	0.49282	0.66193	0.0959*
H6	0.43564	0.38561	0.56747	0.0681*
H3A	0.06170	0.10231	−0.07305	0.0475*
H4A	−0.026 (2)	0.298 (11)	−0.141 (4)	0.0556*
H4B	0.006 (2)	0.363 (12)	−0.218 (4)	0.0556*
H10	0.22764	0.61712	0.18040	0.0978*
H11	0.21460	0.32500	0.30771	0.1128*
H12	0.13680	0.08032	0.28412	0.1061*
H13	0.06966	0.14431	0.13169	0.0717*

	U11	U22	U33	U12	U13	U23
Cl1	0.0933 (12)	0.1012 (16)	0.0900 (12)	−0.0555 (11)	−0.0160 (9)	0.0057 (11)
O1	0.083 (3)	0.0225 (19)	0.088 (3)	−0.0036 (18)	0.034 (2)	−0.0005 (19)
N1	0.055 (2)	0.021 (2)	0.055 (2)	−0.0018 (17)	0.0199 (19)	−0.0024 (18)
N2	0.057 (3)	0.032 (2)	0.060 (3)	−0.002 (2)	0.023 (2)	−0.002 (2)
C1	0.046 (3)	0.034 (3)	0.050 (3)	−0.002 (2)	0.012 (2)	0.013 (2)
C2	0.054 (3)	0.076 (5)	0.067 (3)	−0.018 (3)	0.006 (3)	0.022 (3)
C3	0.053 (3)	0.115 (7)	0.112 (6)	−0.008 (4)	0.023 (4)	0.046 (5)
C4	0.080 (5)	0.129 (8)	0.112 (6)	0.017 (5)	0.052 (5)	0.015 (6)
C5	0.095 (5)	0.082 (5)	0.073 (4)	0.020 (4)	0.042 (4)	0.005 (4)
C6	0.066 (3)	0.048 (3)	0.062 (3)	0.004 (3)	0.025 (3)	0.002 (3)
C7	0.055 (3)	0.022 (3)	0.041 (2)	−0.005 (2)	0.009 (2)	−0.003 (2)
Cl2	0.0653 (9)	0.0623 (10)	0.1057 (12)	−0.0121 (8)	0.0360 (8)	−0.0044 (9)
O2	0.067 (2)	0.0225 (19)	0.075 (2)	0.0001 (16)	−0.0040 (18)	0.0014 (17)
N3	0.049 (2)	0.019 (2)	0.048 (2)	0.0053 (16)	0.0041 (16)	−0.0001 (17)
N4	0.056 (2)	0.034 (3)	0.044 (2)	−0.001 (2)	0.0032 (19)	−0.0001 (19)
C8	0.046 (3)	0.037 (3)	0.042 (2)	0.008 (2)	0.007 (2)	−0.006 (2)
C9	0.046 (3)	0.055 (4)	0.060 (3)	0.009 (2)	0.007 (2)	−0.019 (3)
C10	0.055 (3)	0.094 (6)	0.084 (5)	0.005 (4)	−0.006 (3)	−0.032 (4)
C11	0.079 (5)	0.126 (7)	0.061 (4)	0.036 (5)	−0.017 (4)	−0.020 (5)
C12	0.112 (6)	0.096 (6)	0.056 (4)	0.051 (5)	0.017 (4)	0.020 (4)
C13	0.070 (3)	0.051 (4)	0.056 (3)	0.007 (3)	0.010 (3)	0.010 (3)
C14	0.049 (3)	0.024 (3)	0.044 (2)	−0.002 (2)	0.012 (2)	0.002 (2)

Cl1—C2	1.749 (6)	C3—C4	1.371 (13)
Cl2—C9	1.743 (6)	C4—C5	1.342 (11)
O1—C7	1.237 (6)	C5—C6	1.366 (9)
O2—C14	1.228 (6)	C3—H3	0.9300
N1—N2	1.400 (6)	C4—H4	0.9300
N1—C7	1.338 (6)	C5—H5	0.9300
N1—H1	0.8600	C6—H6	0.9300
N2—H2A	0.89 (6)	C8—C14	1.497 (6)
N2—H2B	0.75 (5)	C8—C9	1.395 (7)
N3—C14	1.317 (6)	C8—C13	1.377 (7)
N3—N4	1.421 (6)	C9—C10	1.370 (9)
N3—H3A	0.8600	C10—C11	1.352 (11)
N4—H4A	0.89 (5)	C11—C12	1.374 (12)
N4—H4B	0.80 (6)	C12—C13	1.384 (9)
C1—C2	1.375 (7)	C10—H10	0.9300
C1—C7	1.484 (7)	C11—H11	0.9300
C1—C6	1.394 (7)	C12—H12	0.9300
C2—C3	1.430 (10)	C13—H13	0.9300
N2—N1—C7	123.0 (4)	C5—C4—H4	119.00
C7—N1—H1	118.00	C3—C4—H4	119.00
N2—N1—H1	119.00	C6—C5—H5	120.00
N1—N2—H2B	110 (4)	C4—C5—H5	120.00
H2A—N2—H2B	97 (6)	C1—C6—H6	119.00
N1—N2—H2A	112 (3)	C5—C6—H6	119.00
N4—N3—C14	122.3 (4)	C9—C8—C13	118.5 (4)
C14—N3—H3A	119.00	C13—C8—C14	119.7 (4)
N4—N3—H3A	119.00	C9—C8—C14	121.7 (4)
N3—N4—H4B	107 (4)	Cl2—C9—C10	118.7 (4)
H4A—N4—H4B	121 (5)	C8—C9—C10	120.6 (5)
N3—N4—H4A	101 (3)	Cl2—C9—C8	120.7 (4)
C6—C1—C7	119.3 (4)	C9—C10—C11	120.0 (6)
C2—C1—C7	122.9 (5)	C10—C11—C12	121.2 (7)
C2—C1—C6	117.7 (5)	C11—C12—C13	119.1 (7)
Cl1—C2—C3	119.8 (5)	C8—C13—C12	120.7 (5)
Cl1—C2—C1	120.0 (4)	O2—C14—C8	121.5 (4)
C1—C2—C3	120.2 (6)	N3—C14—C8	115.4 (4)
C2—C3—C4	118.5 (7)	O2—C14—N3	123.1 (4)
C3—C4—C5	121.4 (8)	C9—C10—H10	120.00
C4—C5—C6	120.2 (7)	C11—C10—H10	120.00
C1—C6—C5	121.9 (5)	C10—C11—H11	120.00
O1—C7—C1	123.0 (4)	C12—C11—H11	119.00
N1—C7—C1	115.3 (4)	C11—C12—H12	120.00
O1—C7—N1	121.6 (4)	C13—C12—H12	120.00
C4—C3—H3	121.00	C8—C13—H13	120.00
C2—C3—H3	121.00	C12—C13—H13	120.00
N2—N1—C7—O1	−3.4 (7)	C3—C4—C5—C6	−0.6 (13)
N2—N1—C7—C1	173.6 (4)	C4—C5—C6—C1	−0.9 (10)
N4—N3—C14—O2	−5.1 (7)	C13—C8—C9—Cl2	179.0 (4)
N4—N3—C14—C8	173.5 (4)	C13—C8—C9—C10	0.6 (8)
C7—C1—C2—Cl1	−2.5 (7)	C14—C8—C9—Cl2	−5.3 (7)
C7—C1—C2—C3	179.2 (6)	C14—C8—C9—C10	176.3 (5)
C2—C1—C6—C5	0.7 (8)	C9—C8—C13—C12	−0.5 (8)
C7—C1—C6—C5	−177.6 (5)	C14—C8—C13—C12	−176.3 (5)
C2—C1—C7—O1	−57.1 (7)	C9—C8—C14—O2	−54.9 (7)
C2—C1—C7—N1	125.9 (5)	C9—C8—C14—N3	126.5 (5)
C6—C1—C7—O1	121.1 (5)	C13—C8—C14—O2	120.7 (5)
C6—C1—C7—N1	−55.9 (6)	C13—C8—C14—N3	−57.9 (6)
C6—C1—C2—C3	1.0 (9)	Cl2—C9—C10—C11	−179.3 (6)
C6—C1—C2—Cl1	179.2 (4)	C8—C9—C10—C11	−0.9 (10)
C1—C2—C3—C4	−2.5 (11)	C9—C10—C11—C12	1.2 (12)
Cl1—C2—C3—C4	179.3 (7)	C10—C11—C12—C13	−1.2 (12)
C2—C3—C4—C5	2.3 (13)	C11—C12—C13—C8	0.8 (10)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.05	2.825 (5)	149
N2—H2A···N2ii	0.89 (6)	2.27 (6)	3.151 (7)	172 (5)
N3—H3A···O2iii	0.86	2.10	2.812 (5)	140
N4—H4B···N4iv	0.80 (6)	2.40 (6)	3.155 (6)	158 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.05	2.825 (5)	149
N2—H2A⋯N2ii	0.89 (6)	2.27 (6)	3.151 (7)	172 (5)
N3—H3A⋯O2iii	0.86	2.10	2.812 (5)	140
N4—H4B⋯N4iv	0.80 (6)	2.40 (6)	3.155 (6)	158 (5)

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