N'-(3-Chloro-benzyl-idene)-4-hy-droxy-benzohydrazide.

The mol-ecule of the title compound, C14H11ClN2O2 adopts an E conformation of the azomethine double bond and the dihedral angle between the benzene rings is 38.96 (13)°. In the crystal, mol-ecules are linked by N-H⋯O and O-H⋯O (with the ketone O atom as acceptor) and C-H⋯O (with the hy-droxy O atom as acceptor) hydrogen bonds, forming a three-dimensional network.

Related literature

For a related structure and background to the chemistry of the N-acyl­hydrazone unit, see: Taha et al. (2012 ▶). For a related structure, see: Hao (2009 ▶).

Experimental

Crystal data

C14H11ClN2O2

M = 274.70

Orthorhombic,

a = 9.0900 (8) Å

b = 9.9396 (9) Å

c = 13.8615 (12) Å

V = 1252.40 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.30 mm−1

T = 293 K

0.27 × 0.11 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.923, T max = 0.970

6999 measured reflections

2274 independent reflections

1980 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.081

S = 1.02

2274 reflections

180 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.20 e Å−3

Absolute structure: Flack (1983 ▶), 1060 Friedel pairs

Flack parameter: 0.12 (9)

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812048325/hb6997sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812048325/hb6997Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812048325/hb6997Isup3.cml

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

C14H11ClN2O2	Dx = 1.457 Mg m−3
Mr = 274.70	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21	Cell parameters from 1415 reflections
a = 9.0900 (8) Å	θ = 2.5–23.8°
b = 9.9396 (9) Å	µ = 0.30 mm−1
c = 13.8615 (12) Å	T = 293 K
V = 1252.40 (19) Å3	Block, colorles
Z = 4	0.27 × 0.11 × 0.10 mm
F(000) = 568

Bruker SMART APEX CCD diffractometer	2274 independent reflections
Radiation source: fine-focus sealed tube	1980 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
ω scan	θmax = 25.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −11→11
Tmin = 0.923, Tmax = 0.970	k = −10→12
6999 measured reflections	l = −15→16

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)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.081	w = 1/[σ2(Fo2) + (0.0383P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2274 reflections	Δρmax = 0.21 e Å−3
180 parameters	Δρmin = −0.20 e Å−3
1 restraint	Absolute structure: Flack (1983), 1060 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.12 (9)

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	0.75369 (7)	0.98855 (8)	0.02100 (8)	0.0540 (2)
O1	1.15017 (17)	0.62769 (17)	0.54009 (13)	0.0374 (4)
O2	0.8459 (2)	0.6183 (2)	0.95100 (14)	0.0518 (6)
H2B	0.874 (4)	0.549 (3)	0.971 (2)	0.059 (11)*
N1	1.0036 (2)	0.7862 (2)	0.41778 (15)	0.0339 (5)
N2	0.9609 (2)	0.7697 (2)	0.51292 (16)	0.0340 (5)
H2A	0.878 (3)	0.799 (2)	0.529 (2)	0.032 (7)*
C1	0.8540 (3)	0.9246 (3)	0.19819 (17)	0.0353 (6)
H1B	0.7633	0.9546	0.2206	0.042*
C2	0.8869 (3)	0.9307 (3)	0.10113 (19)	0.0359 (6)
C3	1.0208 (3)	0.8895 (3)	0.06536 (19)	0.0391 (7)
H3A	1.0407	0.8931	−0.0004	0.047*
C4	1.1252 (3)	0.8426 (3)	0.1302 (2)	0.0437 (7)
H4A	1.2175	0.8169	0.1078	0.052*
C5	1.0943 (3)	0.8336 (3)	0.2265 (2)	0.0405 (7)
H5A	1.1654	0.8008	0.2686	0.049*
C6	0.9579 (3)	0.8729 (2)	0.26244 (17)	0.0317 (6)
C7	0.9198 (3)	0.8545 (2)	0.36386 (18)	0.0354 (6)
H7A	0.8344	0.8927	0.3887	0.043*
C8	1.0415 (3)	0.6900 (2)	0.57049 (19)	0.0307 (6)
C9	0.9925 (2)	0.6764 (2)	0.67131 (18)	0.0301 (6)
C10	1.0357 (3)	0.5631 (3)	0.72305 (19)	0.0349 (6)
H10A	1.0971	0.5003	0.6938	0.042*
C11	0.9897 (3)	0.5416 (3)	0.81628 (18)	0.0357 (6)
H11A	1.0196	0.4651	0.8496	0.043*
C12	0.8986 (3)	0.6348 (3)	0.85996 (18)	0.0364 (6)
C13	0.8576 (3)	0.7497 (3)	0.81142 (19)	0.0446 (7)
H13A	0.7991	0.8137	0.8419	0.053*
C14	0.9029 (3)	0.7698 (3)	0.71824 (18)	0.0400 (6)
H14A	0.8735	0.8471	0.6857	0.048*

	U11	U22	U33	U12	U13	U23
Cl1	0.0529 (4)	0.0712 (5)	0.0378 (4)	0.0143 (4)	−0.0044 (4)	0.0075 (4)
O1	0.0349 (9)	0.0442 (10)	0.0330 (11)	0.0057 (8)	0.0062 (8)	−0.0020 (8)
O2	0.0712 (14)	0.0554 (15)	0.0289 (12)	0.0118 (11)	0.0139 (10)	0.0100 (11)
N1	0.0393 (12)	0.0384 (12)	0.0240 (12)	−0.0034 (10)	0.0052 (9)	0.0007 (9)
N2	0.0333 (11)	0.0452 (13)	0.0237 (12)	0.0008 (10)	0.0092 (11)	0.0022 (11)
C1	0.0346 (13)	0.0401 (15)	0.0311 (16)	0.0029 (12)	0.0072 (11)	0.0000 (11)
C2	0.0440 (15)	0.0345 (15)	0.0292 (15)	0.0000 (11)	−0.0006 (12)	0.0019 (11)
C3	0.0500 (16)	0.0418 (16)	0.0255 (15)	0.0020 (13)	0.0134 (12)	0.0053 (12)
C4	0.0408 (15)	0.0499 (18)	0.0403 (19)	0.0084 (13)	0.0128 (13)	0.0071 (14)
C5	0.0395 (14)	0.0500 (17)	0.0321 (16)	0.0065 (13)	0.0040 (12)	0.0058 (13)
C6	0.0386 (14)	0.0308 (14)	0.0257 (15)	−0.0007 (11)	0.0042 (11)	0.0033 (12)
C7	0.0364 (14)	0.0384 (16)	0.0315 (16)	0.0025 (12)	0.0065 (12)	−0.0004 (13)
C8	0.0299 (12)	0.0322 (14)	0.0299 (15)	−0.0051 (11)	−0.0001 (10)	−0.0018 (11)
C9	0.0295 (13)	0.0356 (15)	0.0252 (15)	−0.0020 (11)	−0.0003 (10)	−0.0020 (11)
C10	0.0355 (13)	0.0359 (15)	0.0332 (16)	0.0057 (12)	0.0009 (12)	−0.0021 (12)
C11	0.0401 (14)	0.0357 (16)	0.0313 (16)	0.0039 (12)	−0.0037 (12)	0.0073 (12)
C12	0.0380 (14)	0.0457 (17)	0.0253 (15)	−0.0034 (12)	0.0009 (12)	0.0010 (13)
C13	0.0578 (17)	0.0432 (16)	0.0327 (16)	0.0138 (13)	0.0094 (13)	−0.0026 (14)
C14	0.0520 (16)	0.0368 (15)	0.0311 (16)	0.0105 (13)	0.0046 (12)	0.0051 (12)

Cl1—C2	1.741 (3)	C5—C6	1.392 (3)
O1—C8	1.240 (3)	C5—H5A	0.9300
O2—C12	1.359 (3)	C6—C7	1.460 (3)
O2—H2B	0.79 (3)	C7—H7A	0.9300
N1—C7	1.265 (3)	C8—C9	1.473 (3)
N1—N2	1.384 (3)	C9—C10	1.392 (3)
N2—C8	1.342 (3)	C9—C14	1.396 (3)
N2—H2A	0.84 (2)	C10—C11	1.375 (3)
C1—C2	1.380 (3)	C10—H10A	0.9300
C1—C6	1.396 (3)	C11—C12	1.382 (4)
C1—H1B	0.9300	C11—H11A	0.9300
C2—C3	1.376 (3)	C12—C13	1.377 (4)
C3—C4	1.388 (4)	C13—C14	1.370 (4)
C3—H3A	0.9300	C13—H13A	0.9300
C4—C5	1.368 (4)	C14—H14A	0.9300
C4—H4A	0.9300
C12—O2—H2B	109 (2)	N1—C7—H7A	120.2
C7—N1—N2	117.2 (2)	C6—C7—H7A	120.2
C8—N2—N1	118.9 (2)	O1—C8—N2	121.9 (2)
C8—N2—H2A	122.6 (19)	O1—C8—C9	121.2 (2)
N1—N2—H2A	117.6 (19)	N2—C8—C9	117.0 (2)
C2—C1—C6	119.4 (2)	C10—C9—C14	117.6 (2)
C2—C1—H1B	120.3	C10—C9—C8	118.6 (2)
C6—C1—H1B	120.3	C14—C9—C8	123.9 (2)
C3—C2—C1	122.0 (2)	C11—C10—C9	121.6 (2)
C3—C2—Cl1	118.9 (2)	C11—C10—H10A	119.2
C1—C2—Cl1	119.1 (2)	C9—C10—H10A	119.2
C2—C3—C4	118.1 (2)	C10—C11—C12	119.3 (2)
C2—C3—H3A	120.9	C10—C11—H11A	120.3
C4—C3—H3A	120.9	C12—C11—H11A	120.3
C5—C4—C3	120.9 (2)	O2—C12—C13	117.2 (2)
C5—C4—H4A	119.6	O2—C12—C11	122.5 (2)
C3—C4—H4A	119.6	C13—C12—C11	120.3 (2)
C4—C5—C6	120.9 (3)	C14—C13—C12	120.0 (2)
C4—C5—H5A	119.5	C14—C13—H13A	120.0
C6—C5—H5A	119.5	C12—C13—H13A	120.0
C5—C6—C1	118.5 (2)	C13—C14—C9	121.1 (2)
C5—C6—C7	121.4 (2)	C13—C14—H14A	119.4
C1—C6—C7	120.0 (2)	C9—C14—H14A	119.4
N1—C7—C6	119.6 (2)
C7—N1—N2—C8	175.3 (2)	N1—N2—C8—C9	179.5 (2)
C6—C1—C2—C3	−1.2 (4)	O1—C8—C9—C10	−21.1 (3)
C6—C1—C2—Cl1	177.28 (19)	N2—C8—C9—C10	157.1 (2)
C1—C2—C3—C4	−1.0 (4)	O1—C8—C9—C14	159.9 (2)
Cl1—C2—C3—C4	−179.4 (2)	N2—C8—C9—C14	−21.9 (3)
C2—C3—C4—C5	2.0 (4)	C14—C9—C10—C11	1.4 (4)
C3—C4—C5—C6	−0.8 (4)	C8—C9—C10—C11	−177.6 (2)
C4—C5—C6—C1	−1.4 (4)	C9—C10—C11—C12	−0.1 (4)
C4—C5—C6—C7	175.4 (3)	C10—C11—C12—O2	178.3 (2)
C2—C1—C6—C5	2.3 (4)	C10—C11—C12—C13	−1.7 (4)
C2—C1—C6—C7	−174.4 (2)	O2—C12—C13—C14	−177.8 (3)
N2—N1—C7—C6	−178.8 (2)	C11—C12—C13—C14	2.3 (4)
C5—C6—C7—N1	−9.2 (4)	C12—C13—C14—C9	−1.0 (4)
C1—C6—C7—N1	167.4 (2)	C10—C9—C14—C13	−0.8 (4)
N1—N2—C8—O1	−2.3 (3)	C8—C9—C14—C13	178.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1i	0.84 (2)	2.20 (2)	3.026 (3)	169 (3)
O2—H2B···O1ii	0.79 (3)	2.01 (3)	2.739 (3)	154 (3)
C4—H4A···O2iii	0.93	2.55	3.216 (3)	128

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1i	0.84 (2)	2.20 (2)	3.026 (3)	169 (3)
O2—H2B⋯O1ii	0.79 (3)	2.01 (3)	2.739 (3)	154 (3)
C4—H4A⋯O2iii	0.93	2.55	3.216 (3)	128

Symmetry codes: (i) ; (ii) ; (iii) .