1-[1-(4-Chloro-phen-yl)ethyl-idene]carbono-hydrazide.

The mol-ecular skeleton of the title mol-ecule, C(9)H(11)ClN(4)O, is essentially planar, the dihedral angle between the ring and the and N/N/C plane being 6.7 (3)°. In the crystal, inter-molecular N-H⋯O and N-H⋯N hydrogen bonds link the mol-ecules into ribbons propagated along [010].

Related literature

For the biological activity of carbonohydrazide derivatives, see: Loncle et al. (2004 ▶). For related structures, see Meyers et al. (1995 ▶).

Experimental

Crystal data

C9H11ClN4O

M = 226.67

Monoclinic,

a = 14.6429 (14) Å

b = 9.6041 (12) Å

c = 7.4327 (9) Å

β = 90.102 (1)°

V = 1045.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.34 mm−1

T = 298 K

0.40 × 0.30 × 0.12 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.875, T max = 0.960

4419 measured reflections

1837 independent reflections

1085 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.126

S = 1.01

1837 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAINT; 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 datablocks I, global. DOI: 10.1107/S1600536809030384/cv2587sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030384/cv2587Isup2.hkl

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

C9H11ClN4O	F(000) = 472
Mr = 226.67	Dx = 1.440 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.6429 (14) Å	Cell parameters from 963 reflections
b = 9.6041 (12) Å	θ = 2.5–22.7°
c = 7.4327 (9) Å	µ = 0.34 mm−1
β = 90.102 (1)°	T = 298 K
V = 1045.3 (2) Å3	Needle, colourless
Z = 4	0.40 × 0.30 × 0.12 mm

Bruker SMART APEX CCD area-detector diffractometer	1837 independent reflections
Radiation source: fine-focus sealed tube	1085 reflections with I > 2σ(I)
graphite	Rint = 0.037
φ and ω scans	θmax = 25.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→17
Tmin = 0.875, Tmax = 0.960	k = −11→11
4419 measured reflections	l = −7→8

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0508P)2 + 0.3562P] where P = (Fo2 + 2Fc2)/3
1837 reflections	(Δ/σ)max = 0.002
137 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.20 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	0.94869 (7)	1.35122 (11)	0.60169 (13)	0.0725 (4)
N1	0.57886 (16)	0.7625 (2)	0.3769 (3)	0.0405 (7)
H1	0.5945	0.6791	0.4057	0.049*
N2	0.63579 (17)	0.8715 (2)	0.4127 (3)	0.0375 (6)
N3	0.47946 (16)	0.9177 (2)	0.2451 (3)	0.0429 (7)
H3	0.5175	0.9828	0.2719	0.051*
N4	0.39947 (16)	0.9500 (2)	0.1494 (3)	0.0434 (7)
H4A	0.4001	0.9058	0.0443	0.065*
H4B	0.3513	0.9224	0.2129	0.065*
O1	0.44329 (14)	0.6900 (2)	0.2677 (3)	0.0460 (6)
C1	0.4970 (2)	0.7867 (3)	0.2949 (4)	0.0358 (7)
C2	0.7519 (2)	0.7025 (3)	0.5085 (4)	0.0518 (9)
H2A	0.7062	0.6479	0.5682	0.078*
H2B	0.8056	0.7075	0.5825	0.078*
H2C	0.7669	0.6601	0.3955	0.078*
C3	0.7158 (2)	0.8469 (3)	0.4762 (4)	0.0357 (7)
C4	0.77306 (19)	0.9705 (3)	0.5105 (4)	0.0353 (7)
C5	0.8596 (2)	0.9605 (3)	0.5861 (4)	0.0458 (8)
H5	0.8821	0.8733	0.6173	0.055*
C6	0.9131 (2)	1.0768 (4)	0.6161 (4)	0.0511 (9)
H6	0.9710	1.0676	0.6663	0.061*
C7	0.8802 (2)	1.2056 (3)	0.5714 (4)	0.0443 (8)
C8	0.7950 (2)	1.2196 (4)	0.4976 (4)	0.0513 (9)
H8	0.7729	1.3074	0.4678	0.062*
C9	0.7423 (2)	1.1031 (3)	0.4676 (4)	0.0475 (9)
H9	0.6845	1.1136	0.4173	0.057*

	U11	U22	U33	U12	U13	U23
Cl1	0.0749 (7)	0.0666 (7)	0.0758 (7)	−0.0359 (5)	−0.0187 (5)	0.0017 (5)
N1	0.0364 (16)	0.0234 (14)	0.0618 (18)	0.0002 (12)	−0.0087 (13)	0.0031 (12)
N2	0.0367 (15)	0.0287 (15)	0.0471 (15)	−0.0058 (12)	−0.0022 (12)	−0.0013 (11)
N3	0.0377 (16)	0.0238 (15)	0.0671 (18)	−0.0020 (12)	−0.0125 (13)	0.0000 (12)
N4	0.0361 (15)	0.0335 (15)	0.0605 (17)	0.0027 (12)	−0.0060 (12)	0.0004 (12)
O1	0.0397 (13)	0.0231 (12)	0.0753 (16)	−0.0055 (10)	−0.0085 (11)	0.0006 (10)
C1	0.0372 (19)	0.0216 (18)	0.0488 (19)	0.0004 (14)	0.0016 (15)	−0.0018 (14)
C2	0.055 (2)	0.043 (2)	0.058 (2)	0.0051 (18)	−0.0117 (17)	−0.0020 (16)
C3	0.0360 (19)	0.0370 (18)	0.0342 (16)	0.0020 (15)	−0.0013 (14)	−0.0022 (14)
C4	0.0332 (18)	0.0379 (19)	0.0349 (17)	−0.0019 (14)	−0.0016 (14)	−0.0011 (14)
C5	0.042 (2)	0.044 (2)	0.051 (2)	−0.0002 (17)	−0.0057 (16)	0.0064 (16)
C6	0.041 (2)	0.061 (3)	0.052 (2)	−0.0070 (19)	−0.0125 (16)	0.0029 (18)
C7	0.045 (2)	0.045 (2)	0.0431 (19)	−0.0125 (17)	−0.0041 (16)	−0.0033 (15)
C8	0.052 (2)	0.037 (2)	0.065 (2)	−0.0075 (17)	−0.0142 (18)	0.0026 (16)
C9	0.0366 (19)	0.042 (2)	0.064 (2)	−0.0034 (16)	−0.0142 (16)	0.0021 (17)

Cl1—C7	1.735 (3)	C2—H2B	0.9600
N1—C1	1.364 (4)	C2—H2C	0.9600
N1—N2	1.364 (3)	C3—C4	1.476 (4)
N1—H1	0.8600	C4—C5	1.388 (4)
N2—C3	1.285 (4)	C4—C9	1.387 (4)
N3—C1	1.336 (3)	C5—C6	1.382 (4)
N3—N4	1.404 (3)	C5—H5	0.9300
N3—H3	0.8600	C6—C7	1.368 (4)
N4—H4A	0.8900	C6—H6	0.9300
N4—H4B	0.8900	C7—C8	1.369 (4)
O1—C1	1.234 (3)	C8—C9	1.378 (4)
C2—C3	1.502 (4)	C8—H8	0.9300
C2—H2A	0.9600	C9—H9	0.9300
C1—N1—N2	119.5 (2)	N2—C3—C2	123.3 (3)
C1—N1—H1	120.2	C4—C3—C2	121.1 (3)
N2—N1—H1	120.3	C5—C4—C9	116.9 (3)
C3—N2—N1	119.1 (2)	C5—C4—C3	122.1 (3)
C1—N3—N4	120.5 (2)	C9—C4—C3	121.0 (3)
C1—N3—H3	119.7	C6—C5—C4	121.7 (3)
N4—N3—H3	119.7	C6—C5—H5	119.1
N3—N4—H4A	109.2	C4—C5—H5	119.1
N3—N4—H4B	109.1	C7—C6—C5	119.5 (3)
H4A—N4—H4B	109.5	C7—C6—H6	120.2
O1—C1—N3	122.8 (3)	C5—C6—H6	120.2
O1—C1—N1	120.3 (3)	C6—C7—C8	120.4 (3)
N3—C1—N1	116.9 (3)	C6—C7—Cl1	119.6 (2)
C3—C2—H2A	109.5	C8—C7—Cl1	119.9 (3)
C3—C2—H2B	109.5	C7—C8—C9	119.7 (3)
H2A—C2—H2B	109.5	C7—C8—H8	120.2
C3—C2—H2C	109.5	C9—C8—H8	120.2
H2A—C2—H2C	109.5	C8—C9—C4	121.8 (3)
H2B—C2—H2C	109.5	C8—C9—H9	119.1
N2—C3—C4	115.6 (3)	C4—C9—H9	119.1

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N4i	0.86	2.24	3.024 (3)	152
N3—H3···O1ii	0.86	2.09	2.850 (3)	147
N4—H4A···O1iii	0.89	2.34	3.206 (3)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N4i	0.86	2.24	3.024 (3)	152
N3—H3⋯O1ii	0.86	2.09	2.850 (3)	147
N4—H4A⋯O1iii	0.89	2.34	3.206 (3)	164

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