N′-(4-Chloro­benzyl­idene)-2-hydroxy­benzohydrazide

Zhang, S.-P.; Qiao, R.; Shao, S.-C.

doi:10.1107/S160053680803972X

organic compounds

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Volume 65| Part 1| January 2009| Page o84

doi:10.1107/S160053680803972X

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N′-(4-Chlorobenzylidene)-2-hydroxybenzohydrazide

Shu-Ping Zhang,^a Rui Qiao ^a and Si-Chang Shao ^a ^*

^aDepartment of Chemistry, Fuyang Normal College, Fuyang Anhui 236041, People's Republic of China
^*Correspondence e-mail: shaosic@fync.edu.cn

(Received 10 November 2008; accepted 25 November 2008; online 10 December 2008)

The title molecule, C₁₄H₁₁ClN₂O₂, adopts a trans configuration with respect to the C=N double bond. An intramolecular N—H⋯O hydrogen bond contributes to molecular conformation and the two benzene rings form a dihedral angle of 17.9 (8)°. In the crystal structure, intermolecular O—H⋯O hydrogen bonds link the molecules into chains running along [10 $[\overline{1}]$ ].

Related literature

For general background to hydrazones and 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_r = 274.70
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.067
wR(F²) = 0.169
S = 1.12
3126 reflections
180 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.22 e Å⁻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) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680803972X/cv2476sup1.cif

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

checkCIF report

Comment top

Hydrazones and Schiff bases have attracted much attention for their excellent biological properties, especially for their potential pharmacological and antitumor properties (Kucukguzel et al., 2006; Khattab, 2005; Karthikeyan et al., 2006; Okabe et al., 1993). We are interested in this fields. As a part of ongoing study, we report herein the crystal structure of the title compound, (I).

The molecular structure of (I) (Fig. 1) displays a trans configuration about the C=N bond. Intramolecular N—H···O hydrogen bond (Table 1) contributes to molecular conformation - the dihedral angle between the two benzene rings is 17.9 (8)°. In the crystal, the molecules are linked into chains by intermolecular O—H···O hydrongen bonds (Table 1).

Related literature top

For general background to hydrazones and 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 top

Equivalent amounts of 2-Hydroxybenzohydrazide and 3-chlorobenzohydrazide were reacted in ethanol (10 mL) for 1 h. After allowing the resulting solution to stand in air for 10 d colourless block-shaped crystals were formed on slow evaporation of the solvent.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme.

N'-(4-Chlorobenzylidene)-2-hydroxybenzohydrazide top

Crystal data top

C₁₄H₁₁ClN₂O₂	F(000) = 568
M_r = 274.70	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0705P)² + 0.4971P] where P = (F_o² + 2F_c²)/3
3126 reflections	(Δ/σ)_max = 0.072
180 parameters	Δρ_max = 0.38 e Å⁻³
1 restraint	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₄H₁₁ClN₂O₂	V = 1305.1 (3) Å³
M_r = 274.70	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 4.8557 (6) Å	µ = 0.29 mm⁻¹
b = 24.588 (3) Å	T = 298 K
c = 11.0903 (13) Å	0.10 × 0.10 × 0.08 mm
β = 99.710 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3126 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2402 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.977	R_int = 0.027
11227 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	1 restraint
wR(F²) = 0.169	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	Δρ_max = 0.38 e Å⁻³
3126 reflections	Δρ_min = −0.22 e Å⁻³
180 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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)

Symmetry code: (i) x+1/2, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁ClN₂O₂
M_r	274.70
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	4.8557 (6), 24.588 (3), 11.0903 (13)
β (°)	99.710 (2)
V (Å³)	1305.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.10 × 0.10 × 0.08

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.972, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	11227, 3126, 2402
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.666

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.169, 1.12
No. of reflections	3126
No. of parameters	180
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.22

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) x+1/2, −y+3/2, z−1/2.

Acknowledgements

This work was supported by the Natural Science Foundation of Anhui Provincial University College (grant No. 2005 KJ137).

References

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