N'-[(1E)-1-(4-Chloro-phen-yl)ethyl-idene]formohydrazide.

The structure of the title compound, C(9)H(9)ClN(2)O, consists of centrosymmetric dimers due to inter-molecular N-H⋯O hydrogen bonding, forming R(2) (2)(8) ring motifs. The dihedral angle between the p-chloro-phenyl unit and the remaining heavy-atom group is 6.77 (17)°.

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For a related structure, see: Guo (2007 ▶).

Experimental

Crystal data

C9H9ClN2O

M = 196.63

Monoclinic,

a = 5.9373 (5) Å

b = 6.2178 (4) Å

c = 25.3495 (18) Å

β = 93.900 (4)°

V = 933.66 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.37 mm−1

T = 296 K

0.25 × 0.22 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.914, T max = 0.940

9690 measured reflections

2311 independent reflections

1426 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.150

S = 1.05

2311 reflections

119 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.20 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 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809037143/bq2157sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809037143/bq2157Isup2.hkl

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

C9H9ClN2O	F(000) = 408
Mr = 196.63	Dx = 1.399 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1864 reflections
a = 5.9373 (5) Å	θ = 2.3–28.0°
b = 6.2178 (4) Å	µ = 0.37 mm−1
c = 25.3495 (18) Å	T = 296 K
β = 93.900 (4)°	Prismatic, colorless
V = 933.66 (12) Å3	0.25 × 0.22 × 0.18 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2311 independent reflections
Radiation source: fine-focus sealed tube	1426 reflections with I > 2σ(I)
graphite	Rint = 0.025
Detector resolution: 7.40 pixels mm-1	θmax = 28.3°, θmin = 3.2°
ω scans	h = −7→7
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −8→8
Tmin = 0.914, Tmax = 0.940	l = −33→32
9690 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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0631P)2 + 0.2896P] where P = (Fo2 + 2Fc2)/3
2311 reflections	(Δ/σ)max < 0.001
119 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.20 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	0.38204 (13)	1.27773 (12)	0.21878 (3)	0.0806 (3)
O1	0.2494 (3)	0.0349 (3)	−0.03180 (7)	0.0740 (7)
N1	0.1941 (3)	0.4376 (3)	0.06100 (7)	0.0500 (6)
N2	0.1350 (3)	0.2578 (3)	0.03140 (7)	0.0536 (7)
C1	0.1329 (3)	0.6969 (3)	0.12510 (8)	0.0447 (7)
C2	0.0192 (4)	0.7732 (4)	0.16716 (9)	0.0611 (9)
C3	0.0928 (4)	0.9511 (4)	0.19580 (10)	0.0654 (9)
C4	0.2836 (4)	1.0560 (4)	0.18273 (9)	0.0523 (8)
C5	0.3992 (4)	0.9858 (4)	0.14095 (10)	0.0622 (9)
C6	0.3239 (4)	0.8092 (4)	0.11281 (9)	0.0593 (8)
C7	0.0599 (4)	0.5018 (3)	0.09485 (8)	0.0481 (7)
C8	−0.1579 (4)	0.3947 (4)	0.10580 (11)	0.0743 (10)
C9	0.2786 (4)	0.1908 (4)	−0.00268 (10)	0.0623 (9)
H2	−0.11039	0.70239	0.17636	0.0733*
H2A	0.00968	0.19185	0.03497	0.0644*
H3	0.01322	0.99959	0.22383	0.0785*
H5	0.52814	1.05794	0.13180	0.0746*
H6	0.40342	0.76308	0.08454	0.0712*
H9	0.41191	0.26791	−0.00468	0.0747*
H81	−0.13024	0.24613	0.11431	0.1115*
H82	−0.26116	0.40444	0.07507	0.1115*
H83	−0.22185	0.46470	0.13504	0.1115*

	U11	U22	U33	U12	U13	U23
Cl1	0.0897 (6)	0.0672 (5)	0.0858 (5)	−0.0185 (3)	0.0123 (4)	−0.0250 (3)
O1	0.0641 (12)	0.0777 (12)	0.0818 (12)	−0.0196 (9)	0.0177 (9)	−0.0322 (10)
N1	0.0503 (11)	0.0477 (10)	0.0521 (10)	−0.0062 (8)	0.0042 (8)	−0.0047 (8)
N2	0.0498 (11)	0.0522 (12)	0.0592 (12)	−0.0094 (9)	0.0059 (9)	−0.0090 (9)
C1	0.0426 (12)	0.0427 (11)	0.0491 (12)	−0.0028 (9)	0.0055 (9)	0.0032 (9)
C2	0.0555 (15)	0.0653 (15)	0.0647 (15)	−0.0166 (12)	0.0207 (11)	−0.0094 (11)
C3	0.0656 (17)	0.0681 (16)	0.0649 (15)	−0.0096 (13)	0.0224 (12)	−0.0138 (12)
C4	0.0548 (14)	0.0467 (12)	0.0553 (13)	−0.0031 (10)	0.0032 (10)	−0.0035 (9)
C5	0.0566 (15)	0.0567 (14)	0.0756 (16)	−0.0178 (11)	0.0215 (12)	−0.0066 (12)
C6	0.0558 (14)	0.0593 (14)	0.0658 (14)	−0.0143 (11)	0.0252 (11)	−0.0120 (11)
C7	0.0454 (12)	0.0467 (12)	0.0524 (12)	−0.0047 (10)	0.0048 (10)	0.0036 (9)
C8	0.0589 (16)	0.0718 (18)	0.0944 (19)	−0.0237 (13)	0.0209 (14)	−0.0215 (14)
C9	0.0531 (15)	0.0669 (16)	0.0677 (16)	−0.0143 (12)	0.0107 (12)	−0.0152 (12)

Cl1—C4	1.733 (3)	C4—C5	1.372 (3)
O1—C9	1.224 (3)	C5—C6	1.368 (3)
N1—N2	1.379 (3)	C7—C8	1.497 (3)
N1—C7	1.274 (3)	C2—H2	0.9300
N2—C9	1.322 (3)	C3—H3	0.9300
N2—H2A	0.8600	C5—H5	0.9300
C1—C2	1.384 (3)	C6—H6	0.9300
C1—C7	1.484 (3)	C8—H81	0.9600
C1—C6	1.385 (3)	C8—H82	0.9600
C2—C3	1.378 (3)	C8—H83	0.9600
C3—C4	1.367 (3)	C9—H9	0.9300
Cl1···C4i	3.535 (2)	H2···C8	2.6200
O1···N2ii	2.920 (3)	H2···H83	1.9000
O1···C8ii	3.288 (3)	H2A···C8	2.4600
O1···C9iii	3.202 (3)	H2A···H81	2.2500
O1···H2Aii	2.0800	H2A···H82	2.3600
O1···H6iv	2.8300	H2A···O1ii	2.0800
O1···H9iii	2.8600	H2A···C9ii	3.0100
O1···H81ii	2.7800	H5···C8ix	2.9100
N2···O1ii	2.920 (3)	H5···H81ix	2.4100
N1···H6	2.4300	H6···N1	2.4300
N2···H81	2.7100	H6···O1iv	2.8300
N2···H82	2.8200	H6···C9iv	2.9100
C4···Cl1v	3.535 (2)	H6···H9iv	2.3700
C7···C9vi	3.537 (3)	H9···O1iii	2.8600
C8···O1ii	3.288 (3)	H9···H6iv	2.3700
C9···O1iii	3.202 (3)	H81···N2	2.7100
C9···C9iii	3.537 (3)	H81···C3x	3.0000
C9···C7vi	3.537 (3)	H81···H2A	2.2500
C2···H83	2.5000	H81···H5viii	2.4100
C3···H81vii	3.0000	H81···O1ii	2.7800
C8···H2A	2.4600	H82···N2	2.8200
C8···H5viii	2.9100	H82···H2A	2.3600
C8···H2	2.6200	H83···C2	2.5000
C9···H2Aii	3.0100	H83···H2	1.9000
C9···H6iv	2.9100
N2—N1—C7	118.23 (18)	O1—C9—N2	124.9 (2)
N1—N2—C9	117.37 (18)	C1—C2—H2	119.00
C9—N2—H2A	121.00	C3—C2—H2	119.00
N1—N2—H2A	121.00	C2—C3—H3	120.00
C6—C1—C7	120.71 (19)	C4—C3—H3	120.00
C2—C1—C7	122.53 (18)	C4—C5—H5	120.00
C2—C1—C6	116.75 (19)	C6—C5—H5	120.00
C1—C2—C3	121.8 (2)	C1—C6—H6	119.00
C2—C3—C4	119.6 (2)	C5—C6—H6	119.00
Cl1—C4—C5	119.44 (19)	C7—C8—H81	109.00
Cl1—C4—C3	120.45 (19)	C7—C8—H82	109.00
C3—C4—C5	120.1 (2)	C7—C8—H83	109.00
C4—C5—C6	119.7 (2)	H81—C8—H82	109.00
C1—C6—C5	122.1 (2)	H81—C8—H83	109.00
N1—C7—C1	115.47 (19)	H82—C8—H83	109.00
N1—C7—C8	124.97 (19)	O1—C9—H9	118.00
C1—C7—C8	119.56 (19)	N2—C9—H9	118.00
C7—N1—N2—C9	−178.5 (2)	C6—C1—C2—C3	−0.5 (3)
N2—N1—C7—C8	1.0 (3)	C7—C1—C2—C3	178.1 (2)
N2—N1—C7—C1	−179.61 (17)	C6—C1—C7—C8	−174.7 (2)
N1—N2—C9—O1	−179.6 (2)	C1—C2—C3—C4	−0.2 (4)
C2—C1—C6—C5	0.6 (3)	C2—C3—C4—C5	0.8 (4)
C7—C1—C6—C5	−178.0 (2)	C2—C3—C4—Cl1	−179.02 (19)
C2—C1—C7—C8	6.7 (3)	Cl1—C4—C5—C6	179.14 (19)
C6—C1—C7—N1	5.9 (3)	C3—C4—C5—C6	−0.7 (4)
C2—C1—C7—N1	−172.7 (2)	C4—C5—C6—C1	−0.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ii	0.8600	2.0800	2.920 (3)	164.00

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1i	0.8600	2.0800	2.920 (3)	164.00

Symmetry code: (i) .