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

The title mol-ecule, C(14)H(11)ClN(2)O(2), adopts a trans configuration with respect to the C=N double bond. An intra-molecular N-H⋯O hydrogen bond contributes to mol-ecular conformation and the two benzene rings form a dihedral angle of 17.9 (8)°. In the crystal structure, inter-molecular O-H⋯O hydrogen bonds link the mol-ecules into chains running along [10].

Related literature

For general background to hydrazones and n class="Chemical">Schiff bases and their potential pharmacological and anti­tumor properties, see: Karthikeyan et al. (2006 ▶); Khattab (2005 ▶); Kucukguzel et al. (2006 ▶); Okabe et al. (1993 ▶).

Experimental

Crystal data

C14H11ClN2O2

M = 274.70

Monoclinic,

a = 4.8557 (6) Å

b = 24.588 (3) Å

c = 11.0903 (13) Å

β = 99.710 (2)°

V = 1305.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 298 (2) K

0.10 × 0.10 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.972, T max = 0.977

11227 measured reflections

3126 independent reflections

2402 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.169

S = 1.12

3126 reflections

180 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.22 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 global, I. DOI: 10.1107/S160053680803972X/cv2476sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680803972X/cv2476Isup2.hkl

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

C14H11ClN2O2	F(000) = 568
Mr = 274.70	Dx = 1.398 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 4.8557 (6) Å	Cell parameters from 986 reflections
b = 24.588 (3) Å	θ = 2.1–28.2°
c = 11.0903 (13) Å	µ = 0.29 mm−1
β = 99.710 (2)°	T = 298 K
V = 1305.1 (3) Å3	Block, colourless
Z = 4	0.10 × 0.10 × 0.08 mm

Bruker SMART CCD area-detector diffractometer	3126 independent reflections
Radiation source: fine-focus sealed tube	2402 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 28.2°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
Tmin = 0.972, Tmax = 0.977	k = −32→31
11227 measured reflections	l = −14→13

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ2(Fo2) + (0.0705P)2 + 0.4971P] where P = (Fo2 + 2Fc2)/3
3126 reflections	(Δ/σ)max = 0.072
180 parameters	Δρmax = 0.38 e Å−3
1 restraint	Δρmin = −0.22 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	−0.39445 (17)	1.00945 (3)	0.73436 (9)	0.0851 (3)
O1	0.9734 (4)	0.73796 (8)	0.50406 (15)	0.0610 (5)
N1	0.6996 (4)	0.76768 (8)	0.67797 (18)	0.0476 (5)
O2	0.8154 (4)	0.72610 (8)	0.85960 (14)	0.0618 (5)
N2	0.5245 (4)	0.80391 (8)	0.72149 (16)	0.0465 (5)
C7	0.8405 (4)	0.73021 (9)	0.75183 (18)	0.0442 (5)
C1	1.0293 (4)	0.69349 (9)	0.69718 (18)	0.0411 (5)
C8	0.3878 (5)	0.83421 (10)	0.6399 (2)	0.0507 (6)
H8	0.4112	0.8294	0.5591	0.061*
C3	1.2815 (5)	0.66229 (11)	0.5401 (2)	0.0531 (6)
H3	1.3252	0.6657	0.4619	0.064*
C2	1.0942 (4)	0.69832 (9)	0.57896 (18)	0.0423 (5)
C4	1.4019 (5)	0.62186 (11)	0.6157 (2)	0.0588 (6)
H4	1.5299	0.5984	0.5892	0.071*
C9	0.1965 (5)	0.87608 (10)	0.6674 (2)	0.0485 (5)
C6	1.1533 (5)	0.65119 (11)	0.7705 (2)	0.0562 (6)
H6	1.1112	0.6471	0.8487	0.067*
C13	−0.0225 (6)	0.93008 (11)	0.8045 (3)	0.0648 (7)
H13	−0.0453	0.9389	0.8838	0.078*
C14	0.1588 (6)	0.88896 (11)	0.7845 (2)	0.0571 (6)
H14	0.2561	0.8698	0.8506	0.069*
C12	−0.1684 (5)	0.95778 (10)	0.7069 (3)	0.0579 (6)
C5	1.3350 (6)	0.61556 (12)	0.7309 (2)	0.0623 (7)
H5	1.4127	0.5873	0.7812	0.075*
C10	0.0436 (6)	0.90483 (13)	0.5712 (3)	0.0713 (8)
H10	0.0643	0.8963	0.4915	0.086*
C11	−0.1375 (6)	0.94547 (13)	0.5903 (3)	0.0763 (9)
H11	−0.2377	0.9644	0.5245	0.092*
H1	1.053 (6)	0.7435 (12)	0.449 (2)	0.081 (10)*
H2	0.708 (5)	0.7692 (10)	0.607 (2)	0.051 (7)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0716 (5)	0.0602 (5)	0.1249 (8)	0.0104 (3)	0.0203 (5)	0.0032 (4)
O1	0.0751 (11)	0.0777 (13)	0.0384 (9)	0.0191 (9)	0.0334 (8)	0.0132 (8)
N1	0.0595 (11)	0.0569 (12)	0.0316 (9)	0.0026 (9)	0.0223 (8)	−0.0021 (8)
O2	0.0829 (12)	0.0735 (12)	0.0359 (8)	0.0106 (9)	0.0301 (8)	0.0019 (8)
N2	0.0528 (10)	0.0519 (11)	0.0384 (10)	−0.0043 (8)	0.0186 (8)	−0.0053 (8)
C7	0.0513 (12)	0.0507 (13)	0.0346 (10)	−0.0096 (10)	0.0191 (9)	−0.0043 (9)
C1	0.0452 (11)	0.0483 (12)	0.0321 (10)	−0.0081 (9)	0.0136 (8)	−0.0037 (9)
C8	0.0585 (13)	0.0622 (15)	0.0342 (11)	−0.0036 (11)	0.0154 (10)	−0.0046 (10)
C3	0.0599 (13)	0.0668 (16)	0.0365 (11)	0.0045 (11)	0.0192 (10)	−0.0054 (11)
C2	0.0459 (11)	0.0513 (13)	0.0320 (10)	−0.0042 (9)	0.0133 (8)	−0.0009 (9)
C4	0.0632 (15)	0.0669 (16)	0.0471 (13)	0.0129 (12)	0.0117 (11)	−0.0114 (12)
C9	0.0514 (12)	0.0545 (14)	0.0401 (11)	−0.0073 (10)	0.0094 (9)	−0.0007 (10)
C6	0.0744 (16)	0.0621 (15)	0.0352 (11)	0.0040 (12)	0.0182 (11)	0.0028 (11)
C13	0.0829 (18)	0.0613 (16)	0.0554 (15)	0.0062 (14)	0.0266 (13)	0.0019 (13)
C14	0.0732 (16)	0.0579 (15)	0.0432 (13)	0.0118 (12)	0.0182 (11)	0.0090 (11)
C12	0.0519 (13)	0.0492 (14)	0.0732 (17)	−0.0039 (11)	0.0120 (12)	0.0066 (12)
C5	0.0808 (18)	0.0614 (16)	0.0441 (13)	0.0150 (13)	0.0084 (12)	0.0032 (12)
C10	0.0768 (18)	0.090 (2)	0.0453 (14)	0.0106 (16)	0.0059 (12)	0.0040 (14)
C11	0.0708 (18)	0.090 (2)	0.0633 (18)	0.0143 (16)	−0.0019 (14)	0.0168 (16)

Cl1—C12	1.739 (3)	C4—C5	1.379 (3)
O1—C2	1.349 (3)	C4—H4	0.9300
O1—H1	0.782 (18)	C9—C14	1.379 (3)
N1—C7	1.341 (3)	C9—C10	1.386 (4)
N1—N2	1.374 (3)	C6—C5	1.367 (3)
N1—H2	0.80 (3)	C6—H6	0.9300
O2—C7	1.226 (2)	C13—C12	1.371 (4)
N2—C8	1.269 (3)	C13—C14	1.383 (4)
C7—C1	1.487 (3)	C13—H13	0.9300
C1—C6	1.393 (3)	C14—H14	0.9300
C1—C2	1.404 (3)	C12—C11	1.360 (4)
C8—C9	1.453 (3)	C5—H5	0.9300
C8—H8	0.9300	C10—C11	1.371 (4)
C3—C4	1.367 (3)	C10—H10	0.9300
C3—C2	1.389 (3)	C11—H11	0.9300
C3—H3	0.9300
C2—O1—H1	112 (2)	C14—C9—C8	123.4 (2)
C7—N1—N2	120.86 (18)	C10—C9—C8	118.6 (2)
C7—N1—H2	122.0 (18)	C5—C6—C1	122.0 (2)
N2—N1—H2	117.1 (18)	C5—C6—H6	119.0
C8—N2—N1	114.23 (18)	C1—C6—H6	119.0
O2—C7—N1	121.9 (2)	C12—C13—C14	119.7 (2)
O2—C7—C1	121.1 (2)	C12—C13—H13	120.2
N1—C7—C1	117.02 (17)	C14—C13—H13	120.2
C6—C1—C2	117.7 (2)	C9—C14—C13	120.5 (2)
C6—C1—C7	116.82 (18)	C9—C14—H14	119.7
C2—C1—C7	125.5 (2)	C13—C14—H14	119.7
N2—C8—C9	122.9 (2)	C11—C12—C13	121.0 (3)
N2—C8—H8	118.6	C11—C12—Cl1	120.2 (2)
C9—C8—H8	118.6	C13—C12—Cl1	118.8 (2)
C4—C3—C2	120.5 (2)	C6—C5—C4	119.4 (2)
C4—C3—H3	119.7	C6—C5—H5	120.3
C2—C3—H3	119.7	C4—C5—H5	120.3
O1—C2—C3	120.60 (18)	C11—C10—C9	121.8 (3)
O1—C2—C1	119.55 (19)	C11—C10—H10	119.1
C3—C2—C1	119.9 (2)	C9—C10—H10	119.1
C3—C4—C5	120.4 (2)	C12—C11—C10	119.1 (3)
C3—C4—H4	119.8	C12—C11—H11	120.5
C5—C4—H4	119.8	C10—C11—H11	120.5
C14—C9—C10	117.9 (2)
C7—N1—N2—C8	−174.7 (2)	N2—C8—C9—C10	−176.0 (2)
N2—N1—C7—O2	1.3 (3)	C2—C1—C6—C5	0.7 (4)
N2—N1—C7—C1	−178.79 (18)	C7—C1—C6—C5	−178.7 (2)
O2—C7—C1—C6	6.2 (3)	C10—C9—C14—C13	−1.2 (4)
N1—C7—C1—C6	−173.7 (2)	C8—C9—C14—C13	178.6 (2)
O2—C7—C1—C2	−173.2 (2)	C12—C13—C14—C9	0.8 (4)
N1—C7—C1—C2	6.9 (3)	C14—C13—C12—C11	−0.1 (4)
N1—N2—C8—C9	−178.5 (2)	C14—C13—C12—Cl1	−179.8 (2)
C4—C3—C2—O1	−179.4 (2)	C1—C6—C5—C4	1.0 (4)
C4—C3—C2—C1	0.5 (4)	C3—C4—C5—C6	−2.0 (4)
C6—C1—C2—O1	178.4 (2)	C14—C9—C10—C11	0.9 (4)
C7—C1—C2—O1	−2.2 (3)	C8—C9—C10—C11	−178.9 (3)
C6—C1—C2—C3	−1.5 (3)	C13—C12—C11—C10	−0.2 (4)
C7—C1—C2—C3	177.9 (2)	Cl1—C12—C11—C10	179.5 (2)
C2—C3—C4—C5	1.3 (4)	C9—C10—C11—C12	−0.2 (5)
N2—C8—C9—C14	4.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H2···O1	0.80 (3)	2.01 (3)	2.624 (2)	134 (2)
O1—H1···O2i	0.78 (2)	1.90 (2)	2.647 (2)	159 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H2⋯O1	0.80 (3)	2.01 (3)	2.624 (2)	134 (2)
O1—H1⋯O2i	0.782 (18)	1.90 (2)	2.647 (2)	159 (3)

Symmetry code: (i) .