(E)-4-Chloro-N′-(4-hydroxy­benzyl­idene)­benzohydrazide

Yang, D.-S.

doi:10.1107/S1600536808027013

organic compounds

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Volume 64| Part 9| September 2008| Page o1849

doi:10.1107/S1600536808027013

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(E)-4-Chloro-N′-(4-hydroxybenzylidene)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, C₁₄H₁₁ClN₂O₂, displays a trans configuration with respect to the C=N double bond. The dihedral angle between the two benzene rings is 12.8 (3)°. In the crystal structure, molecules are linked through intermolecular O—H⋯O and N—H⋯O hydrogen bonds and C—H⋯π interactions, forming a three-dimensional network.

Related literature

For related structures, see: Yang (2007 , 2008a ,b ). For bond-length data, see: Allen et al. (1987 ). For related literature, see: Bernardo et al. (1996 ); Musie et al. (2001 ); Paul et al. (2002 ).

Experimental

Crystal data

C₁₄H₁₁ClN₂O₂
M_r = 274.70
Orthorhombic, P b c a
a = 26.251 (3) Å
b = 12.376 (3) Å
c = 7.786 (2) Å
V = 2529.5 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 298 (2) K
0.13 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.963, T_max = 0.971
11323 measured reflections
2164 independent reflections
1462 reflections with I > 2σ(I)
R_int = 0.078

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.116
S = 1.02
2164 reflections
176 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2ⁱ	0.90 (1)	2.078 (11)	2.970 (3)	171 (3)
O1—H1⋯O2ⁱⁱ	0.82	1.91	2.725 (3)	170
C6—H6⋯Cg1ⁱⁱⁱ	0.93	2.88	3.726 (3)	152
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (iii) $[-x+{\script{1\over 2}}, -y+2, z-{\script{1\over 2}}]$ . Cg1 is the C1–C6 ring centroid.

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/S1600536808027013/ci2657sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808027013/ci2657Isup2.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 12.8 (3)°. All the bonds are within normal ranges (Allen et al., 1987). The C7?N1 bond length of 1.268 (3) Å conforms to the value for a double bond. The bond length of 1.339 (3) Å between atoms C8 and N2 is intermediate between a C—N single bond and a C?N double bond, because of conjugation effects in the molecule.

In the crystal structure, molecules are linked through intermolecular O—H···O and N—H···O hydrogen bonds, and C—H···π interactions (Table 1), forming a three-dimensional network (Fig. 2).

Related literature top

For related structures, see: Yang (2007, 2008a,b). For bond-length data, see: Allen et al. (1987). For related literature, see: Bernardo et al. (1996); Musie et al. (2001); Paul et al. (2002). Cg1 is the C1–C6 ring centroid.

Experimental top

4-Hydroxybenzaldehyde (0.1 mmol, 12.2 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. Crystals of the title compound were formed by gradual evaporation of the solvent over a period of 5 days 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 b axis. H atoms not involved hydrogen bonding (dashed lines) have been omitted for clarity.

(E)-4-Chloro-N'-(4-hydroxybenzylidene)benzohydrazide top

Crystal data top

C₁₄H₁₁ClN₂O₂	F(000) = 1136
M_r = 274.70	D_x = 1.443 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1916 reflections
a = 26.251 (3) Å	θ = 2.3–24.5°
b = 12.376 (3) Å	µ = 0.30 mm⁻¹
c = 7.786 (2) Å	T = 298 K
V = 2529.5 (9) Å³	Block, colourless
Z = 8	0.13 × 0.12 × 0.10 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2164 independent reflections
Radiation source: fine-focus sealed tube	1462 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.078
ω scans	θ_max = 24.9°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −30→31
T_min = 0.963, T_max = 0.971	k = −14→11
11323 measured reflections	l = −8→9

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0433P)² + 1.3235P] where P = (F_o² + 2F_c²)/3
2164 reflections	(Δ/σ)_max = 0.001
176 parameters	Δρ_max = 0.27 e Å⁻³
1 restraint	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₁₄H₁₁ClN₂O₂	V = 2529.5 (9) Å³
M_r = 274.70	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 26.251 (3) Å	µ = 0.30 mm⁻¹
b = 12.376 (3) Å	T = 298 K
c = 7.786 (2) Å	0.13 × 0.12 × 0.10 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2164 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1462 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.971	R_int = 0.078
11323 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	1 restraint
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.27 e Å⁻³
2164 reflections	Δρ_min = −0.36 e Å⁻³
176 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	−0.11993 (3)	0.56136 (8)	−0.02967 (12)	0.0721 (3)
N1	0.15097 (8)	0.76262 (18)	0.3530 (3)	0.0421 (6)
N2	0.10461 (9)	0.74598 (18)	0.2709 (3)	0.0401 (6)
O1	0.37436 (7)	0.92023 (16)	0.5358 (3)	0.0554 (6)
H1	0.3853	0.9786	0.5022	0.083*
O2	0.08473 (7)	0.61751 (14)	0.4644 (2)	0.0412 (5)
C1	0.22762 (10)	0.8643 (2)	0.3633 (3)	0.0378 (7)
C2	0.25323 (10)	0.7913 (2)	0.4685 (4)	0.0450 (7)
H2	0.2372	0.7273	0.5004	0.054*
C3	0.30150 (10)	0.8119 (2)	0.5258 (4)	0.0463 (8)
H3	0.3178	0.7630	0.5979	0.056*
C4	0.32601 (10)	0.9058 (2)	0.4761 (3)	0.0394 (7)
C5	0.30142 (10)	0.9795 (2)	0.3730 (4)	0.0427 (7)
H5	0.3176	1.0435	0.3418	0.051*
C6	0.25282 (10)	0.9580 (2)	0.3163 (4)	0.0440 (7)
H6	0.2366	1.0075	0.2449	0.053*
C7	0.17709 (10)	0.8413 (2)	0.2970 (4)	0.0430 (7)
H7	0.1636	0.8853	0.2116	0.052*
C8	0.07391 (10)	0.6686 (2)	0.3321 (3)	0.0351 (6)
C9	0.02586 (9)	0.6472 (2)	0.2385 (3)	0.0335 (6)
C10	−0.00001 (10)	0.7240 (2)	0.1430 (4)	0.0409 (7)
H10	0.0134	0.7933	0.1331	0.049*
C11	−0.04545 (10)	0.6992 (2)	0.0619 (4)	0.0441 (7)
H11	−0.0628	0.7512	−0.0013	0.053*
C12	−0.06436 (10)	0.5965 (2)	0.0767 (3)	0.0435 (7)
C13	−0.03996 (10)	0.5193 (2)	0.1731 (4)	0.0476 (8)
H13	−0.0536	0.4502	0.1827	0.057*
C14	0.00479 (10)	0.5449 (2)	0.2554 (3)	0.0425 (7)
H14	0.0210	0.4934	0.3229	0.051*
H2A	0.1010 (12)	0.783 (2)	0.172 (2)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0490 (5)	0.0779 (6)	0.0895 (7)	−0.0117 (4)	−0.0259 (5)	0.0004 (5)
N1	0.0359 (13)	0.0460 (15)	0.0443 (14)	−0.0041 (11)	−0.0089 (11)	0.0015 (12)
N2	0.0355 (13)	0.0423 (14)	0.0424 (13)	−0.0048 (11)	−0.0094 (11)	0.0047 (11)
O1	0.0404 (13)	0.0531 (14)	0.0726 (15)	−0.0084 (9)	−0.0133 (11)	0.0061 (12)
O2	0.0436 (11)	0.0403 (11)	0.0398 (10)	0.0025 (9)	−0.0063 (9)	0.0053 (9)
C1	0.0356 (16)	0.0400 (16)	0.0379 (15)	−0.0022 (13)	−0.0013 (13)	−0.0006 (13)
C2	0.0419 (17)	0.0391 (16)	0.0539 (18)	−0.0091 (13)	−0.0022 (15)	0.0060 (14)
C3	0.0428 (18)	0.0409 (17)	0.0552 (19)	−0.0001 (13)	−0.0092 (15)	0.0096 (15)
C4	0.0321 (16)	0.0425 (17)	0.0437 (16)	−0.0009 (12)	−0.0019 (13)	−0.0058 (14)
C5	0.0437 (17)	0.0371 (16)	0.0472 (17)	−0.0063 (13)	0.0020 (14)	0.0023 (14)
C6	0.0423 (17)	0.0450 (18)	0.0447 (17)	−0.0012 (14)	−0.0075 (14)	0.0094 (13)
C7	0.0400 (17)	0.0448 (18)	0.0442 (17)	−0.0007 (14)	−0.0071 (13)	0.0045 (14)
C8	0.0365 (16)	0.0323 (15)	0.0365 (15)	0.0047 (13)	−0.0008 (12)	−0.0052 (13)
C9	0.0318 (15)	0.0361 (16)	0.0325 (14)	0.0037 (12)	0.0025 (12)	0.0007 (12)
C10	0.0392 (16)	0.0353 (16)	0.0480 (16)	−0.0046 (13)	−0.0025 (14)	0.0027 (13)
C11	0.0391 (16)	0.0483 (18)	0.0449 (17)	0.0014 (14)	−0.0064 (14)	0.0077 (14)
C12	0.0333 (16)	0.0520 (19)	0.0451 (17)	−0.0032 (14)	−0.0032 (13)	−0.0031 (15)
C13	0.0441 (18)	0.0426 (18)	0.0560 (19)	−0.0116 (14)	−0.0027 (15)	0.0030 (15)
C14	0.0431 (17)	0.0408 (17)	0.0438 (16)	−0.0003 (14)	−0.0046 (14)	0.0064 (14)

Geometric parameters (Å, º) top

Cl1—C12	1.733 (3)	C5—C6	1.376 (4)
N1—C7	1.268 (3)	C5—H5	0.93
N1—N2	1.390 (3)	C6—H6	0.93
N2—C8	1.339 (3)	C7—H7	0.93
N2—H2A	0.899 (10)	C8—C9	1.481 (3)
O1—C4	1.363 (3)	C9—C10	1.385 (3)
O1—H1	0.82	C9—C14	1.387 (4)
O2—C8	1.242 (3)	C10—C11	1.384 (4)
C1—C6	1.385 (4)	C10—H10	0.93
C1—C2	1.392 (4)	C11—C12	1.369 (4)
C1—C7	1.451 (4)	C11—H11	0.93
C2—C3	1.367 (4)	C12—C13	1.373 (4)
C2—H2	0.93	C13—C14	1.375 (4)
C3—C4	1.383 (4)	C13—H13	0.93
C3—H3	0.93	C14—H14	0.93
C4—C5	1.377 (4)

C7—N1—N2	115.4 (2)	N1—C7—H7	119.3
C8—N2—N1	118.0 (2)	C1—C7—H7	119.3
C8—N2—H2A	127 (2)	O2—C8—N2	121.5 (2)
N1—N2—H2A	114 (2)	O2—C8—C9	120.8 (2)
C4—O1—H1	109.5	N2—C8—C9	117.8 (2)
C6—C1—C2	117.9 (2)	C10—C9—C14	118.8 (2)
C6—C1—C7	120.4 (2)	C10—C9—C8	124.0 (2)
C2—C1—C7	121.6 (2)	C14—C9—C8	117.2 (2)
C3—C2—C1	121.2 (3)	C11—C10—C9	121.0 (2)
C3—C2—H2	119.4	C11—C10—H10	119.5
C1—C2—H2	119.4	C9—C10—H10	119.5
C2—C3—C4	119.8 (3)	C12—C11—C10	118.7 (3)
C2—C3—H3	120.1	C12—C11—H11	120.6
C4—C3—H3	120.1	C10—C11—H11	120.6
O1—C4—C5	123.3 (2)	C11—C12—C13	121.5 (3)
O1—C4—C3	116.6 (2)	C11—C12—Cl1	119.8 (2)
C5—C4—C3	120.1 (3)	C13—C12—Cl1	118.7 (2)
C6—C5—C4	119.6 (3)	C12—C13—C14	119.5 (3)
C6—C5—H5	120.2	C12—C13—H13	120.2
C4—C5—H5	120.2	C14—C13—H13	120.2
C5—C6—C1	121.3 (3)	C13—C14—C9	120.4 (3)
C5—C6—H6	119.3	C13—C14—H14	119.8
C1—C6—H6	119.3	C9—C14—H14	119.8
N1—C7—C1	121.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2ⁱ	0.90 (1)	2.08 (1)	2.970 (3)	171 (3)
O1—H1···O2ⁱⁱ	0.82	1.91	2.725 (3)	170
C6—H6···Cg1ⁱⁱⁱ	0.93	2.88	3.726 (3)	152

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₁ClN₂O₂
M_r	274.70
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	26.251 (3), 12.376 (3), 7.786 (2)
V (Å³)	2529.5 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.13 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.963, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	11323, 2164, 1462
R_int	0.078
(sin θ/λ)_max (Å⁻¹)	0.592

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.116, 1.02
No. of reflections	2164
No. of parameters	176
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)	0.27, −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
N2—H2A···O2ⁱ	0.90 (1)	2.078 (11)	2.970 (3)	171 (3)
O1—H1···O2ⁱⁱ	0.82	1.91	2.725 (3)	170
C6—H6···Cg1ⁱⁱⁱ	0.93	2.88	3.726 (3)	152

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