(E)-2-Chloro-N'-(4-hy-droxy-benzyl-idene)-benzohydrazide.

The title hydrazone mol-ecule, C(14)H(11)ClN(2)O(2), has a trans conformation with respect to the methyl-idene unit. The dihedral angle between the two benzene rings is 37.6 (3)°. In the crystal, the presence of O-H⋯O, O-H⋯N and N-H⋯O hydrogen bonds leads to the formation of a three-dimensional network. The title compound crystallized in the chiral ortho-rhom-bic space group P2(1)2(1)2(1) and was refined as an inversion twin [Flack parameter = -0.20 (18)].

Related literature

For the syntheses and crystal structures of hydrazone compounds, see: Hashemian et al. (2011 ▶); Lei (2011 ▶); Shalash et al. (2010 ▶). For the crystal structures of similar compounds, reported recently by the author, see: Li (2011a ▶,b ▶).

Experimental

Crystal data

C14H11ClN2O2

M = 274.70

Orthorhombic,

a = 7.627 (3) Å

b = 11.859 (2) Å

c = 14.297 (2) Å

V = 1293.2 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 298 K

0.18 × 0.17 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.949, T max = 0.952

6966 measured reflections

2408 independent reflections

1717 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.167

S = 1.07

2408 reflections

176 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.74 e Å−3

Δρmin = −0.35 e Å−3

Absolute structure: Flack (1983 ▶), 999 Friedel pairs

Flack parameter: −0.20 (18)

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536812005661/su2376sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005661/su2376Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812005661/su2376Isup3.cml

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

C14H11ClN2O2	F(000) = 568
Mr = 274.70	Dx = 1.411 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1608 reflections
a = 7.627 (3) Å	θ = 2.2–24.3°
b = 11.859 (2) Å	µ = 0.29 mm−1
c = 14.297 (2) Å	T = 298 K
V = 1293.2 (5) Å3	Block, colourless
Z = 4	0.18 × 0.17 × 0.17 mm

Bruker SMART CCD area-detector diffractometer	2408 independent reflections
Radiation source: fine-focus sealed tube	1717 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
ω scans	θmax = 25.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→8
Tmin = 0.949, Tmax = 0.952	k = −14→9
6966 measured reflections	l = −17→17

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)] = 0.058	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.167	w = 1/[σ2(Fo2) + (0.0863P)2 + 0.1245P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2408 reflections	Δρmax = 0.74 e Å−3
176 parameters	Δρmin = −0.35 e Å−3
1 restraint	Absolute structure: Flack (1983), 999 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.20 (18)

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	0.7790 (2)	1.15240 (11)	0.03121 (11)	0.0961 (6)
N1	0.8701 (5)	0.7962 (3)	0.0532 (2)	0.0446 (9)
N2	0.8920 (5)	0.7314 (3)	−0.0268 (2)	0.0442 (8)
O1	0.9755 (4)	0.9473 (2)	−0.02416 (18)	0.0479 (8)
O2	0.8755 (4)	0.3362 (2)	−0.32680 (17)	0.0439 (7)
H2	0.9466	0.3582	−0.3657	0.066*
C1	0.8856 (5)	0.9734 (3)	0.1347 (3)	0.0405 (10)
C2	0.8308 (6)	1.0829 (4)	0.1335 (3)	0.0521 (12)
C3	0.8123 (6)	1.1435 (5)	0.2166 (4)	0.0698 (15)
H3	0.7742	1.2180	0.2156	0.084*
C4	0.8506 (8)	1.0924 (6)	0.2987 (4)	0.0780 (18)
H4	0.8395	1.1328	0.3541	0.094*
C5	0.9046 (7)	0.9840 (6)	0.3022 (3)	0.0729 (16)
H5	0.9287	0.9510	0.3598	0.087*
C6	0.9240 (6)	0.9228 (5)	0.2230 (3)	0.0551 (12)
H6	0.9621	0.8484	0.2260	0.066*
C7	0.9150 (5)	0.9061 (3)	0.0472 (3)	0.0368 (9)
C8	0.8585 (5)	0.6256 (3)	−0.0187 (3)	0.0408 (9)
H8	0.8278	0.5966	0.0395	0.049*
C9	0.8678 (5)	0.5508 (3)	−0.0988 (2)	0.0375 (9)
C10	0.8151 (6)	0.4403 (3)	−0.0916 (3)	0.0430 (10)
H10	0.7773	0.4128	−0.0341	0.052*
C11	0.8172 (6)	0.3700 (3)	−0.1673 (3)	0.0433 (10)
H11	0.7812	0.2955	−0.1607	0.052*
C12	0.8724 (5)	0.4086 (3)	−0.2536 (2)	0.0335 (8)
C13	0.9259 (5)	0.5197 (3)	−0.2627 (3)	0.0387 (9)
H13	0.9637	0.5465	−0.3204	0.046*
C14	0.9231 (5)	0.5905 (3)	−0.1863 (3)	0.0413 (10)
H14	0.9581	0.6652	−0.1929	0.050*
H1	0.802 (6)	0.767 (4)	0.098 (3)	0.080*

	U11	U22	U33	U12	U13	U23
Cl1	0.1370 (15)	0.0600 (8)	0.0912 (11)	0.0223 (9)	0.0056 (10)	0.0157 (8)
N1	0.062 (2)	0.0378 (19)	0.0339 (18)	−0.0073 (18)	0.0079 (17)	−0.0053 (14)
N2	0.062 (2)	0.0404 (19)	0.0304 (17)	−0.0049 (17)	0.0069 (18)	−0.0085 (15)
O1	0.069 (2)	0.0401 (15)	0.0349 (14)	−0.0095 (14)	0.0108 (14)	−0.0016 (13)
O2	0.063 (2)	0.0377 (15)	0.0310 (14)	−0.0025 (15)	0.0058 (13)	−0.0083 (12)
C1	0.040 (2)	0.043 (2)	0.038 (2)	−0.007 (2)	0.0070 (18)	−0.0085 (18)
C2	0.054 (3)	0.047 (3)	0.055 (3)	−0.010 (2)	0.011 (2)	−0.012 (2)
C3	0.061 (3)	0.057 (3)	0.091 (4)	−0.013 (3)	0.025 (3)	−0.027 (3)
C4	0.074 (4)	0.094 (5)	0.066 (4)	−0.027 (4)	0.015 (3)	−0.041 (3)
C5	0.078 (4)	0.102 (5)	0.039 (3)	−0.013 (4)	−0.003 (2)	−0.013 (3)
C6	0.057 (3)	0.076 (3)	0.032 (2)	−0.010 (2)	0.0049 (19)	−0.014 (2)
C7	0.039 (2)	0.038 (2)	0.033 (2)	−0.0001 (18)	0.0004 (17)	−0.0018 (17)
C8	0.048 (2)	0.044 (2)	0.0309 (19)	−0.002 (2)	−0.0013 (19)	−0.0076 (17)
C9	0.042 (2)	0.037 (2)	0.0332 (19)	0.001 (2)	0.0016 (17)	−0.0013 (17)
C10	0.061 (3)	0.038 (2)	0.0300 (19)	0.002 (2)	0.0041 (18)	0.0006 (17)
C11	0.060 (3)	0.030 (2)	0.040 (2)	0.0002 (19)	0.006 (2)	0.0002 (16)
C12	0.038 (2)	0.0296 (19)	0.0330 (19)	0.0046 (17)	−0.0029 (16)	−0.0027 (15)
C13	0.044 (2)	0.044 (2)	0.0284 (19)	0.0010 (18)	0.0038 (16)	0.0011 (17)
C14	0.054 (3)	0.030 (2)	0.040 (2)	−0.0063 (19)	0.0028 (19)	−0.0012 (17)

Cl1—C2	1.724 (5)	C5—C6	1.353 (6)
N1—C7	1.350 (5)	C5—H5	0.9300
N1—N2	1.388 (4)	C6—H6	0.9300
N1—H1	0.896 (10)	C8—C9	1.450 (5)
N2—C8	1.286 (5)	C8—H8	0.9300
O1—C7	1.222 (5)	C9—C10	1.375 (5)
O2—C12	1.354 (4)	C9—C14	1.402 (5)
O2—H2	0.8200	C10—C11	1.366 (5)
C1—C2	1.364 (6)	C10—H10	0.9300
C1—C6	1.429 (6)	C11—C12	1.382 (5)
C1—C7	1.500 (5)	C11—H11	0.9300
C2—C3	1.396 (7)	C12—C13	1.384 (5)
C3—C4	1.353 (8)	C13—C14	1.377 (5)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.350 (9)	C14—H14	0.9300
C4—H4	0.9300
C7—N1—N2	116.9 (3)	O1—C7—C1	122.7 (3)
C7—N1—H1	125 (3)	N1—C7—C1	115.1 (3)
N2—N1—H1	116 (3)	N2—C8—C9	121.1 (4)
C8—N2—N1	116.2 (3)	N2—C8—H8	119.5
C12—O2—H2	109.5	C9—C8—H8	119.5
C2—C1—C6	118.3 (4)	C10—C9—C14	118.3 (3)
C2—C1—C7	122.8 (4)	C10—C9—C8	120.7 (3)
C6—C1—C7	118.8 (4)	C14—C9—C8	120.9 (3)
C1—C2—C3	120.7 (5)	C11—C10—C9	121.3 (4)
C1—C2—Cl1	122.4 (3)	C11—C10—H10	119.3
C3—C2—Cl1	116.9 (4)	C9—C10—H10	119.3
C4—C3—C2	119.1 (5)	C10—C11—C12	120.5 (3)
C4—C3—H3	120.5	C10—C11—H11	119.7
C2—C3—H3	120.5	C12—C11—H11	119.7
C5—C4—C3	121.6 (5)	O2—C12—C11	119.0 (3)
C5—C4—H4	119.2	O2—C12—C13	121.8 (3)
C3—C4—H4	119.2	C11—C12—C13	119.3 (3)
C4—C5—C6	120.9 (5)	C14—C13—C12	120.1 (3)
C4—C5—H5	119.6	C14—C13—H13	120.0
C6—C5—H5	119.6	C12—C13—H13	120.0
C5—C6—C1	119.5 (5)	C13—C14—C9	120.5 (4)
C5—C6—H6	120.3	C13—C14—H14	119.7
C1—C6—H6	120.3	C9—C14—H14	119.7
O1—C7—N1	122.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.82	1.99	2.751 (4)	155
O2—H2···N2i	0.82	2.48	3.012 (4)	124
N1—H1···O2ii	0.90 (1)	2.12 (2)	2.987 (4)	164 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.82	1.99	2.751 (4)	155
O2—H2⋯N2i	0.82	2.48	3.012 (4)	124
N1—H1⋯O2ii	0.90 (1)	2.12 (2)	2.987 (4)	164 (5)

Symmetry codes: (i) ; (ii) .