N'-(2-Chloro-benzyl-idene)-4-hydroxy-benzohydrazide.

In the mol-ecule of the title compound, C(14)H(11)ClN(2)O(2), the dihedral angle between the benzene rings is 30.53 (4)°. In the crystal structure, inter-molecular O-H⋯O and N-H⋯O hydrogen bonds link the mol-ecules into a two-dimensional network. π-π contacts between benzene rings [centroid-centroid distance = 3.619 (1) Å] may further stabilize the structure. The crystal studied was found to be an inversion twin.

Related literature

For general background, see: Ali et al. (2008 ▶); Dao et al. (2000 ▶); Kargar et al. (2009 ▶); Karthikeyan et al. (2006 ▶); Sriram et al. (2006 ▶); Yeap et al. (2009 ▶). For related structures, see: Eltayeb et al. (2008 ▶); Fun et al. (2009 ▶); Hao (2009 ▶); Nadeem et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H11ClN2O2

M = 274.70

Orthorhombic,

a = 7.2851 (17) Å

b = 11.716 (3) Å

c = 14.978 (3) Å

V = 1278.4 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.30 mm−1

T = 298 K

0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.943, T max = 0.948

6989 measured reflections

2360 independent reflections

1617 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.105

S = 1.02

2360 reflections

176 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.26 e Å−3

Absolute structure: Flack (1983 ▶), 963 Friedel pairs

Flack parameter: 0.45 (12)

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809030797/hk2750sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030797/hk2750Isup2.hkl

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

C14H11ClN2O2	F(000) = 568
Mr = 274.70	Dx = 1.427 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1016 reflections
a = 7.2851 (17) Å	θ = 2.4–24.5°
b = 11.716 (3) Å	µ = 0.30 mm−1
c = 14.978 (3) Å	T = 298 K
V = 1278.4 (5) Å3	Block, yellow
Z = 4	0.20 × 0.20 × 0.18 mm

Bruker SMART CCD area-detector diffractometer	2360 independent reflections
Radiation source: fine-focus sealed tube	1617 reflections with I > 2σ(I)
graphite	Rint = 0.045
ω scans	θmax = 25.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.943, Tmax = 0.948	k = −14→13
6989 measured reflections	l = −16→18

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)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.105	w = 1/[σ2(Fo2) + (0.0459P)2 + 0.0042P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2360 reflections	Δρmax = 0.15 e Å−3
176 parameters	Δρmin = −0.26 e Å−3
1 restraint	Absolute structure: Flack (1983), 963 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.45 (12)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.01997 (17)	0.34021 (7)	1.00869 (6)	0.0874 (4)
O1	0.1624 (4)	0.92529 (17)	1.04651 (12)	0.0549 (6)
O2	0.1212 (3)	1.16180 (18)	0.67205 (12)	0.0510 (6)
H2	0.1881	1.1358	0.6330	0.077*
N1	0.1278 (4)	0.69987 (19)	1.04360 (14)	0.0437 (7)
N2	0.1146 (4)	0.7642 (2)	0.96676 (14)	0.0440 (7)
C1	0.1105 (4)	0.5194 (2)	1.11448 (19)	0.0410 (7)
C2	0.0682 (4)	0.4040 (3)	1.1104 (2)	0.0512 (9)
C3	0.0627 (4)	0.3368 (3)	1.1861 (3)	0.0616 (10)
H3	0.0335	0.2597	1.1817	0.074*
C4	0.1006 (5)	0.3842 (3)	1.2681 (2)	0.0640 (10)
H4	0.0949	0.3394	1.3192	0.077*
C5	0.1472 (5)	0.4985 (3)	1.2746 (2)	0.0588 (10)
H5	0.1749	0.5303	1.3298	0.071*
C6	0.1523 (4)	0.5648 (3)	1.19849 (19)	0.0473 (8)
H6	0.1841	0.6415	1.2032	0.057*
C7	0.1054 (4)	0.5933 (2)	1.03614 (19)	0.0439 (8)
H7	0.0855	0.5617	0.9800	0.053*
C8	0.1310 (4)	0.8794 (2)	0.97441 (17)	0.0377 (7)
C9	0.1139 (4)	0.9470 (2)	0.89145 (17)	0.0352 (7)
C10	0.1551 (4)	0.9036 (2)	0.80756 (17)	0.0394 (7)
H10	0.1814	0.8263	0.8012	0.047*
C11	0.1576 (4)	0.9737 (2)	0.73349 (18)	0.0416 (8)
H11	0.1876	0.9443	0.6777	0.050*
C12	0.1154 (4)	1.0875 (2)	0.74280 (16)	0.0364 (7)
C13	0.0671 (4)	1.1313 (2)	0.82502 (17)	0.0412 (7)
H13	0.0335	1.2075	0.8306	0.049*
C14	0.0692 (4)	1.0614 (2)	0.89873 (18)	0.0409 (8)
H14	0.0401	1.0915	0.9544	0.049*
H2A	0.074 (5)	0.729 (3)	0.9172 (14)	0.080*

	U11	U22	U33	U12	U13	U23
Cl1	0.1341 (10)	0.0427 (5)	0.0854 (7)	−0.0074 (6)	−0.0095 (7)	−0.0113 (5)
O1	0.0965 (19)	0.0376 (12)	0.0307 (11)	0.0005 (12)	−0.0119 (12)	−0.0021 (10)
O2	0.0687 (16)	0.0474 (13)	0.0370 (11)	0.0128 (13)	0.0090 (11)	0.0133 (10)
N1	0.0627 (18)	0.0340 (15)	0.0344 (13)	−0.0020 (13)	−0.0077 (14)	0.0041 (11)
N2	0.067 (2)	0.0337 (14)	0.0308 (13)	−0.0053 (13)	−0.0059 (15)	0.0026 (11)
C1	0.0396 (19)	0.0398 (18)	0.0435 (17)	0.0050 (15)	0.0051 (16)	0.0050 (14)
C2	0.054 (2)	0.0396 (19)	0.0604 (19)	0.0031 (15)	0.0022 (18)	0.0074 (16)
C3	0.052 (2)	0.043 (2)	0.089 (3)	−0.0012 (18)	0.008 (2)	0.026 (2)
C4	0.057 (2)	0.068 (3)	0.067 (2)	0.0149 (19)	0.011 (2)	0.0335 (19)
C5	0.064 (2)	0.065 (3)	0.048 (2)	0.011 (2)	0.0036 (19)	0.0125 (18)
C6	0.049 (2)	0.049 (2)	0.0434 (18)	0.0043 (16)	0.0009 (17)	0.0087 (16)
C7	0.056 (2)	0.0378 (18)	0.0378 (16)	0.0035 (16)	0.0009 (17)	−0.0018 (14)
C8	0.0477 (19)	0.0360 (16)	0.0294 (15)	−0.0026 (14)	−0.0012 (15)	0.0003 (12)
C9	0.0418 (18)	0.0320 (16)	0.0317 (14)	−0.0026 (13)	−0.0054 (15)	0.0005 (12)
C10	0.052 (2)	0.0340 (17)	0.0325 (15)	0.0014 (15)	0.0012 (15)	−0.0014 (13)
C11	0.052 (2)	0.0432 (19)	0.0297 (16)	0.0042 (16)	0.0012 (15)	−0.0009 (13)
C12	0.0416 (18)	0.0381 (17)	0.0295 (15)	0.0000 (15)	−0.0015 (15)	0.0083 (13)
C13	0.055 (2)	0.0309 (16)	0.0377 (16)	0.0052 (14)	0.0017 (15)	0.0004 (13)
C14	0.057 (2)	0.0345 (17)	0.0316 (15)	−0.0006 (14)	0.0032 (15)	−0.0025 (13)

Cl1—C2	1.732 (3)	C5—C6	1.380 (4)
O1—C8	1.228 (3)	C5—H5	0.9300
O2—C12	1.372 (3)	C6—H6	0.9300
O2—H2	0.8200	C7—H7	0.9300
N1—N2	1.379 (3)	C8—C9	1.479 (4)
N1—C7	1.264 (3)	C9—C14	1.383 (4)
N2—C8	1.360 (3)	C9—C10	1.388 (4)
N2—H2A	0.90 (3)	C10—C11	1.381 (4)
C1—C2	1.388 (4)	C10—H10	0.9300
C1—C6	1.400 (4)	C11—C12	1.375 (4)
C1—C7	1.459 (4)	C11—H11	0.9300
C2—C3	1.381 (4)	C12—C13	1.380 (4)
C3—C4	1.376 (5)	C13—C14	1.375 (4)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.384 (5)	C14—H14	0.9300
C4—H4	0.9300
C12—O2—H2	109.5	N1—C7—H7	119.6
C7—N1—N2	117.2 (2)	C1—C7—H7	119.6
N1—N2—H2A	118 (2)	O1—C8—N2	121.7 (2)
C8—N2—N1	117.8 (2)	O1—C8—C9	121.4 (2)
C8—N2—H2A	123 (2)	N2—C8—C9	117.0 (2)
C2—C1—C6	117.3 (3)	C14—C9—C10	118.5 (2)
C2—C1—C7	122.5 (3)	C14—C9—C8	118.2 (2)
C6—C1—C7	120.2 (3)	C10—C9—C8	123.1 (3)
C3—C2—C1	121.7 (3)	C11—C10—C9	120.8 (3)
C3—C2—Cl1	118.0 (3)	C11—C10—H10	119.6
C1—C2—Cl1	120.3 (2)	C9—C10—H10	119.6
C4—C3—C2	119.8 (3)	C12—C11—C10	119.5 (2)
C4—C3—H3	120.1	C12—C11—H11	120.2
C2—C3—H3	120.1	C10—C11—H11	120.2
C3—C4—C5	120.2 (3)	O2—C12—C11	122.0 (2)
C3—C4—H4	119.9	O2—C12—C13	117.5 (2)
C5—C4—H4	119.9	C11—C12—C13	120.5 (2)
C6—C5—C4	119.6 (3)	C14—C13—C12	119.5 (3)
C6—C5—H5	120.2	C14—C13—H13	120.2
C4—C5—H5	120.2	C12—C13—H13	120.2
C5—C6—C1	121.5 (3)	C13—C14—C9	121.1 (3)
C5—C6—H6	119.2	C13—C14—H14	119.5
C1—C6—H6	119.2	C9—C14—H14	119.5
N1—C7—C1	120.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.82	1.84	2.657 (3)	179
N2—H2A···O2ii	0.90 (3)	2.11 (2)	2.951 (3)	157 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.82	1.84	2.657 (3)	179
N2—H2A⋯O2ii	0.90 (3)	2.106 (17)	2.951 (3)	157 (3)

Symmetry codes: (i) ; (ii) .