(E)-4-Chloro-N'-[1-(4-hydroxy-phenyl)-ethylidene]benzohydrazide.

The mol-ecule of the title compound, C(15)H(13)ClN(2)O(2), displays a trans configuration with respect to the C=N double bond. The dihedral angle between the two benzene rings is 15.1 (3)°. A strong intra-molecular O-H⋯N hydrogen bond is observed. In the crystal structure, mol-ecules are linked through inter-molecular N-H⋯O hydrogen bonds, forming chains running along [101].

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Yang (2007 ▶, 2008a ▶,b ▶). For general background, see: Bernardo et al. (1996 ▶); Musie et al. (2001 ▶); Paul et al. (2002 ▶).

Experimental

Crystal data

C15H13ClN2O2

M = 288.72

Monoclinic,

a = 7.241 (3) Å

b = 23.653 (4) Å

c = 8.744 (3) Å

β = 113.682 (3)°

V = 1371.5 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 298 (2) K

0.32 × 0.30 × 0.28 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.915, T max = 0.925

11286 measured reflections

2961 independent reflections

1543 reflections with I > 2σ(I)

R int = 0.071

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.143

S = 0.99

2961 reflections

186 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAIn class="Chemical">NT; 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/S1600536808027001/ci2658sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808027001/ci2658Isup2.hkl

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

C15H13ClN2O2	F000 = 600
Mr = 288.72	Dx = 1.398 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 872 reflections
a = 7.241 (3) Å	θ = 2.6–24.5º
b = 23.653 (4) Å	µ = 0.28 mm−1
c = 8.744 (3) Å	T = 298 (2) K
β = 113.682 (3)º	Block, colourless
V = 1371.5 (8) Å3	0.32 × 0.30 × 0.28 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2961 independent reflections
Radiation source: fine-focus sealed tube	1543 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.071
T = 298(2) K	θmax = 27.0º
ω scans	θmin = 1.7º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.916, Tmax = 0.926	k = −29→30
11286 measured reflections	l = −10→11

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) = 0.144	w = 1/[σ2(Fo2) + (0.0561P)2] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max = 0.001
2961 reflections	Δρmax = 0.26 e Å−3
186 parameters	Δρmin = −0.22 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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	0.37849 (13)	0.06661 (4)	1.09548 (11)	0.0828 (4)
O1	0.1545 (3)	0.20127 (8)	0.3759 (2)	0.0617 (6)
O2	0.2459 (4)	0.30219 (8)	0.1123 (2)	0.0631 (6)
H2	0.2524	0.2888	0.2008	0.095*
N1	0.3189 (3)	0.27241 (9)	0.5512 (3)	0.0434 (6)
N2	0.3039 (3)	0.30449 (9)	0.4155 (3)	0.0420 (6)
C1	0.2803 (4)	0.18339 (11)	0.6672 (3)	0.0435 (7)
C2	0.2877 (4)	0.20451 (11)	0.8154 (3)	0.0478 (7)
H2A	0.2731	0.2432	0.8265	0.057*
C3	0.3166 (4)	0.16914 (12)	0.9483 (4)	0.0524 (8)
H3	0.3197	0.1834	1.0483	0.063*
C4	0.3408 (4)	0.11202 (12)	0.9296 (4)	0.0503 (8)
C5	0.3352 (4)	0.08999 (12)	0.7838 (4)	0.0563 (8)
H5	0.3533	0.0514	0.7742	0.068*
C6	0.3026 (4)	0.12538 (12)	0.6515 (3)	0.0502 (7)
H6	0.2952	0.1106	0.5506	0.060*
C7	0.2461 (4)	0.21899 (11)	0.5182 (3)	0.0438 (7)
C8	0.3356 (4)	0.35814 (11)	0.4314 (3)	0.0382 (6)
C9	0.3192 (4)	0.38770 (10)	0.2801 (3)	0.0374 (6)
C10	0.2770 (4)	0.35866 (11)	0.1294 (3)	0.0460 (7)
C11	0.2624 (5)	0.38790 (14)	−0.0107 (4)	0.0678 (9)
H11	0.2341	0.3684	−0.1099	0.081*
C12	0.2887 (5)	0.44553 (14)	−0.0070 (4)	0.0739 (10)
H12	0.2794	0.4647	−0.1027	0.089*
C13	0.3289 (5)	0.47455 (13)	0.1384 (4)	0.0662 (9)
H13	0.3462	0.5136	0.1416	0.079*
C14	0.3432 (4)	0.44635 (11)	0.2775 (4)	0.0520 (8)
H14	0.3702	0.4667	0.3750	0.062*
C15	0.3841 (4)	0.38928 (11)	0.5915 (3)	0.0533 (8)
H15A	0.3203	0.3708	0.6553	0.080*
H15B	0.3357	0.4274	0.5679	0.080*
H15C	0.5275	0.3896	0.6543	0.080*
H1	0.418 (3)	0.2788 (12)	0.651 (2)	0.080*

	U11	U22	U33	U12	U13	U23
Cl1	0.0724 (6)	0.0858 (7)	0.0841 (7)	−0.0001 (5)	0.0252 (5)	0.0420 (5)
O1	0.0699 (14)	0.0514 (12)	0.0387 (12)	−0.0031 (10)	−0.0045 (11)	−0.0021 (10)
O2	0.0910 (16)	0.0491 (13)	0.0491 (13)	−0.0110 (11)	0.0281 (13)	−0.0078 (10)
N1	0.0459 (14)	0.0396 (13)	0.0356 (13)	−0.0033 (11)	0.0068 (11)	0.0045 (11)
N2	0.0423 (14)	0.0440 (14)	0.0352 (13)	−0.0002 (11)	0.0109 (11)	0.0046 (11)
C1	0.0350 (16)	0.0387 (17)	0.0471 (18)	−0.0031 (12)	0.0064 (13)	0.0007 (13)
C2	0.0458 (18)	0.0406 (16)	0.0527 (19)	−0.0054 (13)	0.0152 (15)	0.0022 (14)
C3	0.0468 (19)	0.061 (2)	0.0483 (19)	−0.0079 (15)	0.0176 (15)	0.0026 (15)
C4	0.0351 (16)	0.055 (2)	0.054 (2)	−0.0018 (14)	0.0112 (14)	0.0203 (15)
C5	0.0476 (19)	0.0370 (17)	0.075 (2)	−0.0006 (13)	0.0151 (17)	0.0109 (16)
C6	0.0485 (18)	0.0444 (18)	0.0493 (18)	−0.0050 (13)	0.0109 (14)	−0.0002 (14)
C7	0.0409 (16)	0.0411 (17)	0.0418 (17)	0.0016 (13)	0.0086 (14)	0.0030 (13)
C8	0.0313 (15)	0.0397 (16)	0.0386 (16)	0.0016 (12)	0.0088 (12)	−0.0008 (12)
C9	0.0321 (14)	0.0415 (16)	0.0361 (15)	0.0031 (12)	0.0109 (12)	0.0035 (12)
C10	0.0499 (18)	0.0441 (18)	0.0441 (17)	0.0026 (13)	0.0190 (14)	0.0020 (14)
C11	0.089 (3)	0.073 (2)	0.0403 (19)	−0.0044 (19)	0.0249 (17)	0.0029 (16)
C12	0.093 (3)	0.069 (2)	0.055 (2)	−0.005 (2)	0.0241 (19)	0.0206 (18)
C13	0.080 (2)	0.050 (2)	0.062 (2)	−0.0014 (17)	0.0216 (19)	0.0116 (17)
C14	0.061 (2)	0.0421 (18)	0.0490 (18)	0.0039 (14)	0.0184 (15)	0.0048 (14)
C15	0.070 (2)	0.0473 (18)	0.0411 (17)	0.0005 (15)	0.0204 (15)	−0.0006 (14)

Cl1—C4	1.736 (3)	C5—H5	0.93
O1—C7	1.225 (3)	C6—H6	0.93
O2—C10	1.353 (3)	C8—C9	1.459 (3)
O2—H2	0.82	C8—C15	1.493 (3)
N1—C7	1.355 (3)	C9—C14	1.400 (3)
N1—N2	1.375 (3)	C9—C10	1.406 (3)
N1—H1	0.896 (10)	C10—C11	1.373 (4)
N2—C8	1.287 (3)	C11—C12	1.375 (4)
C1—C2	1.370 (4)	C11—H11	0.93
C1—C6	1.395 (4)	C12—C13	1.369 (4)
C1—C7	1.486 (4)	C12—H12	0.93
C2—C3	1.377 (4)	C13—C14	1.354 (4)
C2—H2A	0.93	C13—H13	0.93
C3—C4	1.381 (4)	C14—H14	0.93
C3—H3	0.93	C15—H15A	0.96
C4—C5	1.363 (4)	C15—H15B	0.96
C5—C6	1.369 (4)	C15—H15C	0.96
C10—O2—H2	109.5	N2—C8—C15	123.5 (2)
C7—N1—N2	116.2 (2)	C9—C8—C15	121.1 (2)
C7—N1—H1	117 (2)	C14—C9—C10	116.8 (2)
N2—N1—H1	120 (2)	C14—C9—C8	121.6 (2)
C8—N2—N1	120.1 (2)	C10—C9—C8	121.6 (2)
C2—C1—C6	119.3 (3)	O2—C10—C11	116.7 (3)
C2—C1—C7	123.5 (2)	O2—C10—C9	123.3 (2)
C6—C1—C7	117.1 (3)	C11—C10—C9	120.0 (3)
C1—C2—C3	120.8 (3)	C10—C11—C12	121.2 (3)
C1—C2—H2A	119.6	C10—C11—H11	119.4
C3—C2—H2A	119.6	C12—C11—H11	119.4
C2—C3—C4	118.6 (3)	C13—C12—C11	119.6 (3)
C2—C3—H3	120.7	C13—C12—H12	120.2
C4—C3—H3	120.7	C11—C12—H12	120.2
C5—C4—C3	121.8 (3)	C14—C13—C12	119.9 (3)
C5—C4—Cl1	118.7 (2)	C14—C13—H13	120.1
C3—C4—Cl1	119.5 (2)	C12—C13—H13	120.1
C4—C5—C6	119.1 (3)	C13—C14—C9	122.5 (3)
C4—C5—H5	120.4	C13—C14—H14	118.7
C6—C5—H5	120.4	C9—C14—H14	118.7
C5—C6—C1	120.4 (3)	C8—C15—H15A	109.5
C5—C6—H6	119.8	C8—C15—H15B	109.5
C1—C6—H6	119.8	H15A—C15—H15B	109.5
O1—C7—N1	122.7 (2)	C8—C15—H15C	109.5
O1—C7—C1	121.9 (2)	H15A—C15—H15C	109.5
N1—C7—C1	115.4 (2)	H15B—C15—H15C	109.5
N2—C8—C9	115.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2	0.82	1.80	2.513 (3)	145
N1—H1···O1i	0.90 (1)	2.074 (11)	2.968 (3)	176 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N2	0.82	1.80	2.513 (3)	145
N1—H1⋯O1i	0.90 (1)	2.074 (11)	2.968 (3)	176 (3)

Symmetry code: (i) .