4-Hy­droxy-N′-[1-(2-hy­droxy­phen­yl)ethyl­idene]benzohydrazide

Ji, X.-H.; Lu, J.-F.

doi:10.1107/S1600536810019914

organic compounds

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Volume 66| Part 6| June 2010| Page o1514

https://doi.org/10.1107/S1600536810019914

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4-Hydroxy-N′-[1-(2-hydroxyphenyl)ethylidene]benzohydrazide

Xiao-Hui Ji ^a and Jiu-Fu Lu ^a ^*

^aSchool of Chemistry and Environmental Science, Shaanxi University of Technology, Hanzhong 723000, People's Republic of China
^*Correspondence e-mail: jiufulu@163.com

(Received 24 May 2010; accepted 26 May 2010; online 29 May 2010)

In the title compound, C₁₅H₁₄N₂O₃, there is an intramolecular O—H⋯N hydrogen bond and the dihedral angle between the two aromatic rings is 13.9 (3)°. In the crystal structure, molecules are stabilized by intermolecular O—H⋯O and N—H⋯O hydrogen bonds.

Related literature

For related structures, see: Lu et al. (2008a ,b ,c ); Xiao & Wei (2009 ); He (2008 ); Shi et al. (2007 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₅H₁₄N₂O₃
M_r = 270.28
Monoclinic, P 2₁ /c
a = 4.926 (2) Å
b = 31.06 (2) Å
c = 8.473 (3) Å
β = 93.852 (3)°
V = 1293.5 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.21 × 0.20 × 0.17 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.980, T_max = 0.984
8965 measured reflections
2770 independent reflections
1569 reflections with I > 2σ(I)
R_int = 0.064

Refinement

R[F² > 2σ(F²)] = 0.069
wR(F²) = 0.172
S = 1.05
2770 reflections
188 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.21 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	1.78	2.499 (3)	146
O3—H3⋯O1ⁱ	0.82	1.97	2.786 (3)	179
N2—H2⋯O2ⁱⁱ	0.90 (1)	2.09 (2)	2.961 (4)	163 (3)
Symmetry codes: (i) $[x-1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x-1, y, z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); 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: https://doi.org/10.1107/S1600536810019914/su2181sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810019914/su2181Isup2.hkl

checkCIF report

Comment top

As part of our investigation of the crystal structures of Schiff bases derived from the condensation of aldehydes or ketones with benzohydrazides (Lu et al., 2008a,b,c), we report herein on the crystal structure of the new title Schiff base compound.

In the title compound, illustrated in Fig. 1, the bond lengths have normal values (Allen et al., 1987), and are comparable to those observed in similar compounds (Xiao & Wei, 2009; He, 2008; Shi et al., 2007). The dihedral angle between the two aromatic rings is 13.9 (3)°, indicating that the Schiff base molecule is slightly twisted. An intramolecular O—H···N hydrogen bond is observed (Table 1).

In the crystal structure, the molecules are stabilized by intermolecular O—H···O and N—H···O hydrogen bonds (Table 1 and Fig. 2).

Related literature top

For related structures, see: Lu et al. (2008a,b,c); Xiao & Wei (2009); He (2008); Shi et al. (2007). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was prepared by the Schiff base condensation of 1-(2-hydroxyphenyl)ethanone (0.1 mol, 13.6 g) and 4-hydroxybenzohydrazide (0.1 mmol, 15.2 g) in 95% ethanol (70 ml). The excess ethanol was removed by distillation. The colourless solid obtained was filtered and washed with ethanol. Single crystals, suitable for X-ray diffraction analysis, were obatined by slow evaporation of a 95% ethanol solution at rt.

Structure description top

In the crystal structure, the molecules are stabilized by intermolecular O—H···O and N—H···O hydrogen bonds (Table 1 and Fig. 2).

For related structures, see: Lu et al. (2008a,b,c); Xiao & Wei (2009); He (2008); Shi et al. (2007). For bond-length data, see: Allen et al. (1987).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. The dashed line indicates the intramolecular O-H···N hydrogen bond (see Table 1 for details.
	Fig. 2. The crystal packing of the title compound, viewed along the c axis. H-atoms not involved in hydrogen bonding (dashed lines) have been omitted for clarity.

4-Hydroxy-N'-[1-(2-hydroxyphenyl)ethylidene]benzohydrazide top

Crystal data top

C₁₅H₁₄N₂O₃	F(000) = 568
M_r = 270.28	D_x = 1.388 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 957 reflections
a = 4.926 (2) Å	θ = 2.5–24.5°
b = 31.06 (2) Å	µ = 0.10 mm⁻¹
c = 8.473 (3) Å	T = 298 K
β = 93.852 (3)°	Block, colourless
V = 1293.5 (11) Å³	0.21 × 0.20 × 0.17 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	2770 independent reflections
Radiation source: fine-focus sealed tube	1569 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.064
ω scans	θ_max = 27.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −6→6
T_min = 0.980, T_max = 0.984	k = −39→34
8965 measured reflections	l = −10→10

Refinement top

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)] = 0.069	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.172	w = 1/[σ²(F_o²) + (0.0649P)² + 0.4306P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2770 reflections	Δρ_max = 0.26 e Å⁻³
188 parameters	Δρ_min = −0.21 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0057 (18)

Crystal data top

C₁₅H₁₄N₂O₃	V = 1293.5 (11) Å³
M_r = 270.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 4.926 (2) Å	µ = 0.10 mm⁻¹
b = 31.06 (2) Å	T = 298 K
c = 8.473 (3) Å	0.21 × 0.20 × 0.17 mm
β = 93.852 (3)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	2770 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	1569 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.984	R_int = 0.064
8965 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	1 restraint
wR(F²) = 0.172	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.26 e Å⁻³
2770 reflections	Δρ_min = −0.21 e Å⁻³
188 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
N1	0.9548 (5)	0.64659 (7)	0.6666 (3)	0.0384 (6)
N2	0.8786 (5)	0.68800 (7)	0.6186 (3)	0.0389 (6)
O1	1.2807 (5)	0.60332 (7)	0.8408 (3)	0.0581 (7)
H1	1.2112	0.6252	0.8021	0.087*
O2	1.3097 (4)	0.71011 (6)	0.6779 (3)	0.0510 (6)
O3	0.7088 (5)	0.89007 (6)	0.5716 (3)	0.0593 (7)
H3	0.5810	0.8920	0.5048	0.089*
C1	0.9088 (6)	0.57209 (9)	0.6782 (3)	0.0377 (7)
C2	1.1338 (6)	0.56842 (9)	0.7889 (3)	0.0413 (8)
C3	1.2167 (7)	0.52855 (10)	0.8469 (4)	0.0530 (9)
H3A	1.3668	0.5266	0.9192	0.064*
C4	1.0804 (8)	0.49197 (10)	0.7992 (4)	0.0603 (10)
H4	1.1375	0.4653	0.8389	0.072*
C5	0.8616 (8)	0.49468 (11)	0.6938 (5)	0.0644 (11)
H5	0.7681	0.4698	0.6618	0.077*
C6	0.7776 (7)	0.53373 (10)	0.6342 (4)	0.0544 (9)
H6	0.6274	0.5348	0.5617	0.065*
C7	0.8165 (6)	0.61399 (9)	0.6136 (3)	0.0366 (7)
C8	1.0701 (6)	0.71922 (9)	0.6405 (3)	0.0374 (7)
C9	0.9732 (6)	0.76376 (9)	0.6167 (3)	0.0346 (7)
C10	0.7529 (6)	0.77407 (9)	0.5133 (3)	0.0394 (7)
H10	0.6639	0.7523	0.4547	0.047*
C11	0.6634 (6)	0.81585 (9)	0.4958 (3)	0.0411 (8)
H11	0.5158	0.8222	0.4254	0.049*
C12	0.7927 (6)	0.84846 (9)	0.5827 (3)	0.0392 (7)
C13	1.0155 (6)	0.83870 (10)	0.6841 (4)	0.0477 (8)
H13	1.1056	0.8605	0.7415	0.057*
C14	1.1051 (6)	0.79695 (10)	0.7005 (4)	0.0446 (8)
H14	1.2560	0.7908	0.7687	0.054*
C15	0.5813 (7)	0.61695 (11)	0.4922 (4)	0.0541 (9)
H15A	0.4183	0.6075	0.5378	0.081*
H15B	0.6154	0.5990	0.4035	0.081*
H15C	0.5595	0.6463	0.4575	0.081*
H2	0.710 (3)	0.6991 (11)	0.622 (4)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0324 (14)	0.0301 (14)	0.0522 (15)	0.0026 (11)	0.0000 (11)	0.0024 (11)
N2	0.0325 (14)	0.0302 (14)	0.0531 (15)	0.0022 (11)	−0.0030 (12)	0.0062 (11)
O1	0.0596 (15)	0.0364 (13)	0.0744 (16)	−0.0035 (11)	−0.0252 (12)	0.0046 (11)
O2	0.0294 (12)	0.0443 (13)	0.0784 (16)	0.0045 (10)	−0.0033 (11)	0.0088 (11)
O3	0.0686 (18)	0.0336 (13)	0.0721 (17)	0.0086 (11)	−0.0224 (13)	−0.0024 (10)
C1	0.0364 (17)	0.0327 (16)	0.0439 (16)	−0.0017 (13)	0.0030 (13)	−0.0025 (13)
C2	0.0458 (19)	0.0313 (17)	0.0464 (17)	−0.0017 (14)	0.0001 (14)	−0.0005 (13)
C3	0.062 (2)	0.0367 (19)	0.060 (2)	0.0050 (16)	−0.0040 (17)	0.0084 (15)
C4	0.077 (3)	0.0292 (19)	0.076 (2)	0.0094 (17)	0.013 (2)	0.0120 (16)
C5	0.072 (3)	0.0326 (19)	0.088 (3)	−0.0091 (18)	0.000 (2)	−0.0022 (17)
C6	0.055 (2)	0.041 (2)	0.066 (2)	−0.0074 (16)	−0.0070 (17)	−0.0049 (16)
C7	0.0340 (17)	0.0351 (16)	0.0405 (16)	0.0006 (13)	−0.0001 (13)	−0.0023 (12)
C8	0.0338 (17)	0.0386 (17)	0.0397 (16)	0.0010 (14)	0.0017 (13)	0.0043 (13)
C9	0.0314 (16)	0.0334 (16)	0.0388 (15)	0.0013 (13)	0.0017 (12)	0.0036 (12)
C10	0.0415 (18)	0.0313 (16)	0.0438 (17)	−0.0016 (13)	−0.0080 (13)	−0.0003 (13)
C11	0.0426 (18)	0.0367 (17)	0.0419 (17)	0.0008 (14)	−0.0125 (14)	0.0048 (13)
C12	0.0450 (18)	0.0277 (16)	0.0445 (17)	0.0026 (13)	−0.0013 (14)	0.0032 (13)
C13	0.046 (2)	0.0353 (18)	0.0588 (19)	−0.0043 (14)	−0.0146 (16)	−0.0076 (15)
C14	0.0380 (18)	0.0428 (18)	0.0509 (19)	0.0019 (15)	−0.0127 (14)	0.0019 (14)
C15	0.049 (2)	0.053 (2)	0.058 (2)	−0.0024 (17)	−0.0111 (16)	0.0030 (16)

Geometric parameters (Å, º) top

N1—C7	1.284 (3)	C5—H5	0.9300
N1—N2	1.393 (3)	C6—H6	0.9300
N2—C8	1.357 (4)	C7—C15	1.500 (4)
N2—H2	0.900 (10)	C8—C9	1.473 (4)
O1—C2	1.360 (3)	C9—C10	1.385 (4)
O1—H1	0.8200	C9—C14	1.388 (4)
O2—C8	1.234 (3)	C10—C11	1.375 (4)
O3—C12	1.358 (3)	C10—H10	0.9300
O3—H3	0.8200	C11—C12	1.382 (4)
C1—C6	1.394 (4)	C11—H11	0.9300
C1—C2	1.407 (4)	C12—C13	1.381 (4)
C1—C7	1.472 (4)	C13—C14	1.374 (4)
C2—C3	1.384 (4)	C13—H13	0.9300
C3—C4	1.367 (4)	C14—H14	0.9300
C3—H3A	0.9300	C15—H15A	0.9600
C4—C5	1.356 (5)	C15—H15B	0.9600
C4—H4	0.9300	C15—H15C	0.9600
C5—C6	1.367 (5)

C7—N1—N2	120.0 (2)	O2—C8—N2	121.0 (3)
C8—N2—N1	116.7 (2)	O2—C8—C9	123.1 (3)
C8—N2—H2	111 (2)	N2—C8—C9	115.9 (2)
N1—N2—H2	125 (2)	C10—C9—C14	118.1 (3)
C2—O1—H1	109.5	C10—C9—C8	122.5 (3)
C12—O3—H3	109.5	C14—C9—C8	119.4 (2)
C6—C1—C2	116.1 (3)	C11—C10—C9	121.2 (3)
C6—C1—C7	122.0 (3)	C11—C10—H10	119.4
C2—C1—C7	121.9 (2)	C9—C10—H10	119.4
O1—C2—C3	117.4 (3)	C10—C11—C12	120.1 (3)
O1—C2—C1	122.0 (2)	C10—C11—H11	120.0
C3—C2—C1	120.6 (3)	C12—C11—H11	120.0
C4—C3—C2	120.7 (3)	O3—C12—C13	118.5 (3)
C4—C3—H3A	119.6	O3—C12—C11	122.2 (3)
C2—C3—H3A	119.6	C13—C12—C11	119.3 (3)
C5—C4—C3	119.8 (3)	C14—C13—C12	120.4 (3)
C5—C4—H4	120.1	C14—C13—H13	119.8
C3—C4—H4	120.1	C12—C13—H13	119.8
C4—C5—C6	120.4 (3)	C13—C14—C9	120.9 (3)
C4—C5—H5	119.8	C13—C14—H14	119.6
C6—C5—H5	119.8	C9—C14—H14	119.6
C5—C6—C1	122.4 (3)	C7—C15—H15A	109.5
C5—C6—H6	118.8	C7—C15—H15B	109.5
C1—C6—H6	118.8	H15A—C15—H15B	109.5
N1—C7—C1	115.0 (2)	C7—C15—H15C	109.5
N1—C7—C15	124.0 (3)	H15A—C15—H15C	109.5
C1—C7—C15	121.0 (3)	H15B—C15—H15C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.78	2.499 (3)	146
O3—H3···O1ⁱ	0.82	1.97	2.786 (3)	179
N2—H2···O2ⁱⁱ	0.90 (1)	2.09 (2)	2.961 (4)	163 (3)

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄N₂O₃
M_r	270.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	4.926 (2), 31.06 (2), 8.473 (3)
β (°)	93.852 (3)
V (Å³)	1293.5 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.21 × 0.20 × 0.17

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.980, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	8965, 2770, 1569
R_int	0.064
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.172, 1.05
No. of reflections	2770
No. of parameters	188
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, −0.21

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), 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	1.78	2.499 (3)	146
O3—H3···O1ⁱ	0.82	1.97	2.786 (3)	179
N2—H2···O2ⁱⁱ	0.90 (1)	2.089 (15)	2.961 (4)	163 (3)

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

Acknowledgements

The authors thank the Scientific Research Foundation of Shaanxi University of Technology (project No. SLGQD0708) for financial support.

References

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