4-Hydr­oxy-N′-(3,5-dichloro-2-hydroxy­benzyl­idene)benzohydrazide

Ren, C.-G.

doi:10.1107/S1600536809020820

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Pages o1503-o1504

doi:10.1107/S1600536809020820

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4-Hydroxy-N′-(3,5-dichloro-2-hydroxybenzylidene)benzohydrazide

Chong-Gui Ren ^a ^*

^aDepartment of Chemistry and Chemical Engineering, Zaozhuang University, Zaozhuang Shandong 277160, People's Republic of China
^*Correspondence e-mail: renchonggui@163.com

(Received 25 May 2009; accepted 2 June 2009; online 6 June 2009)

In the title compound, C₁₄H₁₀Cl₂N₂O₃, the dihedral angle between the two benzene rings is 5.1 (2)°. The molecule adopts an E configuration with respect to the C=N bond and an intramolecular O—H⋯N interaction is present. In the crystal structure, molecules are linked through intermolecular N—H⋯O and O—H⋯O hydrogen bonds.

Related literature

For the biological properties of Schiff base compounds, see: Jeewoth et al. (1999 ); Ren et al. (2002 ); Eltayeb et al. (2008 ); Sinha et al. (2008 ). For metal complexes of Schiff base compounds, see: Shivakumar et al. (2008 ); Prabhakaran et al. (2006 ); Dhar et al. (2005 ). For related structures, see: Cui et al. (2007 ); Jing et al. (2007 ); Ma et al. (2008 ); Salhin et al. (2007 ); Lin et al. (2007 ); Alhadi et al. (2008 ); Xue et al. (2008 ); Wang et al. (2008 ); Lu (2008 ); Diao et al. (2008 ); Qiu (2009 ); Mohd Lair et al. (2009a ,b ). For reference structural data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₄H₁₀Cl₂N₂O₃
M_r = 325.14
Monoclinic, P 2₁ /c
a = 8.030 (1) Å
b = 13.546 (2) Å
c = 13.433 (2) Å
β = 107.247 (2)°
V = 1395.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.48 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 = 0.911, T_max = 0.919
8463 measured reflections
3039 independent reflections
2324 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.107
S = 1.03
3039 reflections
195 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.90	2.6164 (19)	145
O3—H3⋯O2ⁱ	0.82	1.85	2.658 (2)	168
N2—H2⋯O3ⁱⁱ	0.899 (10)	2.204 (16)	3.000 (2)	147 (2)
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809020820/bx2214sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809020820/bx2214Isup2.hkl

checkCIF report

Comment top

The Schiff base compounds show excellent biological properties (Jeewoth et al., 1999; Ren et al., 2002; Eltayeb et al., 2008; Sinha et al., 2008). Moreover, the Schiff base compounds have been widely used as versatile ligands in coordination chemistry (Shivakumar et al., 2008; Prabhakaran et al., 2006; Dhar et al., 2005). We report here the crystal structure of the title compound. In the title compound, Fig. 1, the dihedral angle between the two benzene rings is 5.1 (2)°. All the bond lengths are within normal values (Allen et al., 1987) and comparable to those in other similar compounds (Cui et al., 2007; Jing et al., 2007; Ma et al., 2008; Salhin et al., 2007; Lin et al., 2007; Alhadi et al., 2008; Xue et al., 2008; Wang et al., 2008; Lu, 2008; Diao et al., 2008; Qiu, 2009; Mohd Lair et al., 2009a,b). —H···N OIn the crystal structure, molecules are linked through intermolecular N–H···O and O–H···O hydrogen bonds (Table 1), Fig. 2.

Related literature top

For the biological properties of Schiff base compounds, see: Jeewoth et al. (1999); Ren et al. (2002); Eltayeb et al. (2008); Sinha et al. (2008). For metal complexes of Schiff base compounds, see: Shivakumar et al. (2008); Prabhakaran et al. (2006); Dhar et al. (2005). For related structures, see: Cui et al. (2007); Jing et al. (2007); Ma et al. (2008); Salhin et al. (2007); Lin et al. (2007); Alhadi et al. (2008); Xue et al. (2008); Wang et al. (2008); Lu (2008); Diao et al. (2008); Qiu (2009); Mohd Lair et al. (2009a,b). For reference structural data, see: Allen et al. (1987).

Experimental top

All the starting materials were obtained with AR grade from Lancaster. 3,5-Dichloro-2-hydroxybenzaldehyde (1.0 mmol, 192.2 mg) and 4-hydroxybenzohydrazide (1.0 mmol, 152.2 mg) were refluxed in 30 ml methanol solution for 30 min giving a clear yellow solution. Yellow block-shaped single crystals of the compound were obtained by slow evaporation of the solution for a week at room temperature.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the compound with 30% probability ellipsoids. The intramolecular O–H···N hydrogen bond is shown as a dashed line.
	Fig. 2. Molecular packing of the compound with hydrogen bonds drawn as dashed lines. Hydrogen atoms not involved in hydrogen bonding have been omitted.

(I) top

Crystal data top

C₁₄H₁₀Cl₂N₂O₃	F(000) = 664
M_r = 325.14	D_x = 1.547 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2634 reflections
a = 8.030 (1) Å	θ = 2.2–26.0°
b = 13.546 (2) Å	µ = 0.48 mm⁻¹
c = 13.433 (2) Å	T = 298 K
β = 107.247 (2)°	Block, yellow
V = 1395.5 (3) Å³	0.20 × 0.20 × 0.18 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3039 independent reflections
Radiation source: fine-focus sealed tube	2324 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ω scans	θ_max = 27.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→9
T_min = 0.911, T_max = 0.919	k = −17→17
8463 measured reflections	l = −17→14

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0503P)² + 0.3954P] where P = (F_o² + 2F_c²)/3
3039 reflections	(Δ/σ)_max = 0.001
195 parameters	Δρ_max = 0.22 e Å⁻³
1 restraint	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₁₄H₁₀Cl₂N₂O₃	V = 1395.5 (3) Å³
M_r = 325.14	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.030 (1) Å	µ = 0.48 mm⁻¹
b = 13.546 (2) Å	T = 298 K
c = 13.433 (2) Å	0.20 × 0.20 × 0.18 mm
β = 107.247 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3039 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2324 reflections with I > 2σ(I)
T_min = 0.911, T_max = 0.919	R_int = 0.023
8463 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	1 restraint
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.22 e Å⁻³
3039 reflections	Δρ_min = −0.36 e Å⁻³
195 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	−0.05205 (8)	0.19042 (4)	1.13049 (5)	0.0682 (2)
Cl2	0.17799 (11)	0.43904 (5)	1.45283 (5)	0.0843 (2)
N1	0.25047 (18)	0.49746 (11)	1.00303 (11)	0.0382 (3)
N2	0.31078 (19)	0.56552 (10)	0.94624 (11)	0.0387 (3)
O1	0.08301 (19)	0.33479 (10)	1.01678 (10)	0.0512 (3)
H1	0.1314	0.3745	0.9885	0.077*
O2	0.26379 (19)	0.45814 (10)	0.81320 (10)	0.0540 (4)
O3	0.55673 (19)	0.80001 (10)	0.59831 (10)	0.0512 (3)
H3	0.6200	0.8433	0.6322	0.077*
C1	0.1834 (2)	0.45241 (12)	1.15726 (13)	0.0369 (4)
C2	0.1046 (2)	0.36288 (13)	1.11609 (14)	0.0384 (4)
C3	0.0458 (2)	0.30054 (13)	1.18096 (15)	0.0422 (4)
C4	0.0667 (2)	0.32330 (14)	1.28362 (15)	0.0467 (5)
H4	0.0275	0.2804	1.3259	0.056*
C5	0.1470 (3)	0.41115 (15)	1.32275 (14)	0.0479 (5)
C6	0.2037 (2)	0.47558 (14)	1.26095 (14)	0.0436 (4)
H6	0.2558	0.5348	1.2885	0.052*
C7	0.2478 (2)	0.52136 (13)	1.09426 (13)	0.0388 (4)
H7	0.2873	0.5833	1.1208	0.047*
C8	0.3119 (2)	0.54031 (13)	0.84892 (13)	0.0366 (4)
C9	0.3736 (2)	0.61545 (12)	0.78824 (13)	0.0354 (4)
C10	0.3425 (3)	0.59603 (15)	0.68236 (14)	0.0468 (4)
H10	0.2799	0.5400	0.6532	0.056*
C11	0.4035 (3)	0.65890 (16)	0.62059 (14)	0.0497 (5)
H11	0.3815	0.6454	0.5500	0.060*
C12	0.4974 (2)	0.74196 (13)	0.66340 (13)	0.0402 (4)
C13	0.5276 (2)	0.76339 (13)	0.76825 (13)	0.0404 (4)
H13	0.5893	0.8199	0.7969	0.049*
C14	0.4656 (2)	0.70024 (13)	0.82994 (13)	0.0383 (4)
H14	0.4856	0.7147	0.9002	0.046*
H2	0.352 (3)	0.6232 (11)	0.9766 (18)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0753 (4)	0.0500 (3)	0.0806 (4)	−0.0224 (3)	0.0252 (3)	−0.0019 (3)
Cl2	0.1359 (6)	0.0822 (5)	0.0491 (3)	−0.0081 (4)	0.0492 (4)	−0.0052 (3)
N1	0.0398 (8)	0.0373 (7)	0.0391 (8)	0.0010 (6)	0.0143 (6)	0.0045 (6)
N2	0.0462 (8)	0.0364 (8)	0.0361 (8)	−0.0036 (6)	0.0165 (7)	0.0022 (6)
O1	0.0629 (9)	0.0480 (8)	0.0433 (7)	−0.0110 (6)	0.0165 (6)	−0.0057 (6)
O2	0.0730 (10)	0.0428 (7)	0.0462 (8)	−0.0120 (7)	0.0174 (7)	−0.0068 (6)
O3	0.0679 (10)	0.0503 (8)	0.0392 (7)	0.0019 (6)	0.0218 (7)	0.0104 (6)
C1	0.0357 (9)	0.0358 (9)	0.0422 (9)	0.0033 (7)	0.0160 (7)	0.0027 (7)
C2	0.0340 (9)	0.0394 (9)	0.0421 (9)	0.0042 (7)	0.0117 (7)	0.0021 (7)
C3	0.0347 (9)	0.0383 (9)	0.0543 (11)	0.0006 (7)	0.0140 (8)	0.0040 (8)
C4	0.0438 (10)	0.0478 (11)	0.0553 (11)	0.0066 (8)	0.0249 (9)	0.0130 (9)
C5	0.0563 (12)	0.0525 (11)	0.0413 (10)	0.0068 (9)	0.0241 (9)	0.0032 (8)
C6	0.0500 (11)	0.0404 (9)	0.0452 (10)	0.0000 (8)	0.0212 (9)	−0.0030 (8)
C7	0.0399 (9)	0.0355 (9)	0.0427 (10)	−0.0012 (7)	0.0147 (8)	−0.0003 (7)
C8	0.0359 (9)	0.0382 (9)	0.0343 (9)	0.0031 (7)	0.0080 (7)	0.0008 (7)
C9	0.0345 (9)	0.0392 (9)	0.0326 (8)	0.0059 (7)	0.0102 (7)	0.0010 (7)
C10	0.0527 (11)	0.0510 (11)	0.0347 (9)	−0.0067 (9)	0.0098 (8)	−0.0043 (8)
C11	0.0588 (12)	0.0615 (12)	0.0276 (9)	−0.0009 (10)	0.0107 (8)	−0.0009 (8)
C12	0.0453 (10)	0.0419 (10)	0.0351 (9)	0.0116 (8)	0.0144 (7)	0.0106 (7)
C13	0.0468 (10)	0.0376 (9)	0.0373 (9)	0.0016 (8)	0.0132 (8)	0.0003 (7)
C14	0.0453 (10)	0.0412 (9)	0.0299 (8)	0.0037 (7)	0.0135 (7)	−0.0014 (7)

Geometric parameters (Å, º) top

Cl1—C3	1.7281 (19)	C4—C5	1.381 (3)
Cl2—C5	1.7321 (19)	C4—H4	0.9300
N1—C7	1.274 (2)	C5—C6	1.372 (3)
N1—N2	1.3732 (19)	C6—H6	0.9300
N2—C8	1.354 (2)	C7—H7	0.9300
N2—H2	0.899 (10)	C8—C9	1.478 (2)
O1—C2	1.348 (2)	C9—C14	1.390 (2)
O1—H1	0.8200	C9—C10	1.394 (2)
O2—C8	1.228 (2)	C10—C11	1.376 (3)
O3—C12	1.363 (2)	C10—H10	0.9300
O3—H3	0.8200	C11—C12	1.381 (3)
C1—C6	1.389 (2)	C11—H11	0.9300
C1—C2	1.403 (2)	C12—C13	1.387 (2)
C1—C7	1.455 (2)	C13—C14	1.383 (2)
C2—C3	1.393 (2)	C13—H13	0.9300
C3—C4	1.374 (3)	C14—H14	0.9300

C7—N1—N2	118.23 (15)	N1—C7—C1	120.45 (16)
C8—N2—N1	118.12 (14)	N1—C7—H7	119.8
C8—N2—H2	123.3 (16)	C1—C7—H7	119.8
N1—N2—H2	118.5 (16)	O2—C8—N2	120.98 (16)
C2—O1—H1	109.5	O2—C8—C9	121.77 (15)
C12—O3—H3	109.5	N2—C8—C9	117.26 (15)
C6—C1—C2	119.72 (16)	C14—C9—C10	118.68 (16)
C6—C1—C7	118.80 (16)	C14—C9—C8	124.85 (15)
C2—C1—C7	121.47 (15)	C10—C9—C8	116.40 (16)
O1—C2—C3	118.68 (16)	C11—C10—C9	120.67 (18)
O1—C2—C1	123.01 (16)	C11—C10—H10	119.7
C3—C2—C1	118.30 (16)	C9—C10—H10	119.7
C4—C3—C2	121.93 (17)	C10—C11—C12	120.06 (16)
C4—C3—Cl1	119.57 (14)	C10—C11—H11	120.0
C2—C3—Cl1	118.49 (15)	C12—C11—H11	120.0
C3—C4—C5	118.66 (17)	O3—C12—C11	117.03 (15)
C3—C4—H4	120.7	O3—C12—C13	122.78 (17)
C5—C4—H4	120.7	C11—C12—C13	120.19 (16)
C6—C5—C4	121.27 (17)	C14—C13—C12	119.56 (17)
C6—C5—Cl2	119.84 (16)	C14—C13—H13	120.2
C4—C5—Cl2	118.89 (15)	C12—C13—H13	120.2
C5—C6—C1	120.10 (17)	C13—C14—C9	120.82 (15)
C5—C6—H6	120.0	C13—C14—H14	119.6
C1—C6—H6	120.0	C9—C14—H14	119.6

C7—N1—N2—C8	−179.36 (15)	C6—C1—C7—N1	171.54 (16)
C6—C1—C2—O1	−178.94 (16)	C2—C1—C7—N1	−7.3 (3)
C7—C1—C2—O1	−0.1 (3)	N1—N2—C8—O2	−1.5 (2)
C6—C1—C2—C3	1.3 (2)	N1—N2—C8—C9	178.67 (14)
C7—C1—C2—C3	−179.91 (16)	O2—C8—C9—C14	−164.75 (17)
O1—C2—C3—C4	178.59 (17)	N2—C8—C9—C14	15.1 (2)
C1—C2—C3—C4	−1.6 (3)	O2—C8—C9—C10	12.3 (2)
O1—C2—C3—Cl1	0.0 (2)	N2—C8—C9—C10	−167.92 (16)
C1—C2—C3—Cl1	179.75 (13)	C14—C9—C10—C11	0.8 (3)
C2—C3—C4—C5	0.6 (3)	C8—C9—C10—C11	−176.42 (17)
Cl1—C3—C4—C5	179.25 (14)	C9—C10—C11—C12	0.3 (3)
C3—C4—C5—C6	0.7 (3)	C10—C11—C12—O3	178.78 (17)
C3—C4—C5—Cl2	−178.61 (15)	C10—C11—C12—C13	−1.3 (3)
C4—C5—C6—C1	−1.0 (3)	O3—C12—C13—C14	−179.03 (16)
Cl2—C5—C6—C1	178.29 (14)	C11—C12—C13—C14	1.0 (3)
C2—C1—C6—C5	0.0 (3)	C12—C13—C14—C9	0.1 (3)
C7—C1—C6—C5	−178.85 (16)	C10—C9—C14—C13	−1.0 (3)
N2—N1—C7—C1	179.32 (14)	C8—C9—C14—C13	175.92 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.90	2.6164 (19)	145
O3—H3···O2ⁱ	0.82	1.85	2.658 (2)	168
N2—H2···O3ⁱⁱ	0.90 (1)	2.20 (2)	3.000 (2)	147 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₀Cl₂N₂O₃
M_r	325.14
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	8.030 (1), 13.546 (2), 13.433 (2)
β (°)	107.247 (2)
V (Å³)	1395.5 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.48
Crystal size (mm)	0.20 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.911, 0.919
No. of measured, independent and observed [I > 2σ(I)] reflections	8463, 3039, 2324
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.107, 1.03
No. of reflections	3039
No. of parameters	195
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)	0.22, −0.36

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), 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
O1—H1···N1	0.82	1.90	2.6164 (19)	145
O3—H3···O2ⁱ	0.82	1.85	2.658 (2)	168
N2—H2···O3ⁱⁱ	0.899 (10)	2.204 (16)	3.000 (2)	147 (2)

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

Acknowledgements

The author acknowledges Zaozhuang University for funding this study.

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