(E)-4-Chloro-N′-[1-(4-hydroxy­phenyl)­ethylidene]benzohydrazide

Yang, D.-S.

doi:10.1107/S1600536808027001

organic compounds

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Volume 64| Part 9| September 2008| Page o1850

doi:10.1107/S1600536808027001

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(E)-4-Chloro-N′-[1-(4-hydroxyphenyl)ethylidene]benzohydrazide

De-Suo Yang ^a ^*

^aDepartment of Chemistry and Chemical Engineering, Baoji University of Arts and Sciences, Baoji 721007, People's Republic of China
^*Correspondence e-mail: desuoyang@yahoo.com.cn

(Received 16 August 2008; accepted 21 August 2008; online 30 August 2008)

The molecule of the title compound, C₁₅H₁₃ClN₂O₂, 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 intramolecular O—H⋯N hydrogen bond is observed. In the crystal structure, molecules are linked through intermolecular 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_r = 288.72
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.058
wR(F²) = 0.143
S = 0.99
2961 reflections
186 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 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
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) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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/S1600536808027001/ci2658sup1.cif

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

checkCIF report

Comment top

Schiff base compounds have been of great interest for a long time. These compounds play an important role in the development of coordination chemistry (Musie et al., 2001; Bernardo et al., 1996; Paul et al., 2002). Recently, we have reported a few Schiff base compounds (Yang, 2007, 2008a,b). As a further investigation of this work, the crystal structure of the title compound is reported here.

The molecule of the title compound displays a trans configuration with respect to the C?N double bond (Fig. 1). The dihedral angle between the two benzene rings is 15.1 (3)°. All the bond lengths are within normal ranges (Allen et al., 1987). The C8═N2 bond length of 1.287 (3) Å conforms to the value for a double bond. The N1—C7 bond length of 1.355 (3) Å is intermediate between a C—N single bond and a C?N double bond, because of conjugation effects in the molecule. There is a strong intramolecular hydrogen bond between the hydroxyl hydrogen and N2.

In the crystal structure, molecules are linked through intermolecular N—H···O hydrogen bonds (Table 1), forming chains running along the [1 0 1] direction (Fig. 2).

Related literature top

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 top

1-(2-Hydroxyphenyl)ethanone (0.1 mmol, 13.6 mg) and 4-chlorobenzohydrazide (0.1 mmol, 17.0 mg) were dissolved in MeOH (10 ml). The mixture was stirred at room temperature to give a clear colourless solution. Single crystals of the title compound were obtained by gradual evaporation of the solvent over a period of 12 d 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 title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Molecular packing as viewed along the c axis. Hydrogen bonds are shown as dashed lines.

(E)-4-Chloro-N'-[1-(4-hydroxyphenyl)ethylidene]benzohydrazide top

Crystal data top

C₁₅H₁₃ClN₂O₂	F(000) = 600
M_r = 288.72	D_x = 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 = 2.6–24.5°
b = 23.653 (4) Å	µ = 0.28 mm⁻¹
c = 8.744 (3) Å	T = 298 K
β = 113.682 (3)°	Block, colourless
V = 1371.5 (8) Å³	0.32 × 0.30 × 0.28 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2961 independent reflections
Radiation source: fine-focus sealed tube	1543 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.071
ω scans	θ_max = 27.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.916, T_max = 0.926	k = −29→30
11286 measured reflections	l = −10→11

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.144	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ²(F_o²) + (0.0561P)²] where P = (F_o² + 2F_c²)/3
2961 reflections	(Δ/σ)_max = 0.001
186 parameters	Δρ_max = 0.26 e Å⁻³
1 restraint	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₅H₁₃ClN₂O₂	V = 1371.5 (8) Å³
M_r = 288.72	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.241 (3) Å	µ = 0.28 mm⁻¹
b = 23.653 (4) Å	T = 298 K
c = 8.744 (3) Å	0.32 × 0.30 × 0.28 mm
β = 113.682 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2961 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1543 reflections with I > 2σ(I)
T_min = 0.916, T_max = 0.926	R_int = 0.071
11286 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	1 restraint
wR(F²) = 0.144	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	Δρ_max = 0.26 e Å⁻³
2961 reflections	Δρ_min = −0.22 e Å⁻³
186 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	0.37849 (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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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)	2.07 (1)	2.968 (3)	176 (3)

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃ClN₂O₂
M_r	288.72
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	7.241 (3), 23.653 (4), 8.744 (3)
β (°)	113.682 (3)
V (Å³)	1371.5 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.32 × 0.30 × 0.28

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.916, 0.926
No. of measured, independent and observed [I > 2σ(I)] reflections	11286, 2961, 1543
R_int	0.071
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.144, 0.99
No. of reflections	2961
No. of parameters	186
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)	0.26, −0.22

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) x+1/2, −y+1/2, z+1/2.

Acknowledgements

The author acknowledges Key Laboratory Construction Support from the Education Office of Shanxi Province (project No. 05JS43).

References

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