4-Hydr­oxy-N′-(2-hydr­oxy-3-methoxy­benzyl­idene)benzohydrazide mono­hydrate

Lu, J.-F.

doi:10.1107/S1600536808030894

organic compounds

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Volume 64| Part 10| October 2008| Page o2032

doi:10.1107/S1600536808030894

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4-Hydroxy-N′-(2-hydroxy-3-methoxybenzylidene)benzohydrazide monohydrate

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 19 September 2008; accepted 25 September 2008; online 27 September 2008)

In the title compound, C₁₅H₁₄N₂O₄·H₂O, the dihedral angle between the two aromatic rings is 33.3 (5)°. The methoxy group is twisted slightly away from the attached benzene ring [C—O—C—C = 13.8 (9)°]. An intramolecular O—H⋯N hydrogen bond is observed. In the crystal structure, the molecules are linked into a two-dimensional network parallel to the (010) plane by intermolecular N—H⋯O, O—H⋯O and C—H⋯O hydrogen bonds

Related literature

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

Experimental

Crystal data

C₁₅H₁₄N₂O₄·H₂O
M_r = 304.30
Monoclinic, P n
a = 4.891 (2) Å
b = 12.171 (5) Å
c = 12.371 (5) Å
β = 95.724 (7)°
V = 732.8 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 (2) K
0.08 × 0.07 × 0.07 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.992, T_max = 0.993
5972 measured reflections
1582 independent reflections
791 reflections with I > 2σ(I)
R_int = 0.086

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.119
S = 0.92
1582 reflections
211 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.15 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	1.99	2.687 (5)	142
N2—H2⋯O5ⁱ	0.90 (3)	1.99 (3)	2.820 (5)	154 (5)
O4—H4⋯O2ⁱⁱ	0.82	2.15	2.872 (7)	147
O5—H5A⋯O3ⁱⁱⁱ	0.86 (3)	1.97 (3)	2.769 (6)	156 (6)
O5—H5B⋯O3^iv	0.84 (4)	2.01 (3)	2.769 (6)	148 (5)
C7—H7⋯O5ⁱ	0.93	2.48	3.229 (7)	138
C14—H14⋯O5ⁱ	0.93	2.34	3.218 (7)	158
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+2, z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{3\over 2}}, -y+2, z-{\script{1\over 2}}]$ ; (iii) x, y, z-1; (iv) x+1, y, z-1.

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: 10.1107/S1600536808030894/ci2678sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808030894/ci2678Isup2.hkl

checkCIF report

Comment top

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

The asymmetric unit of the title compound (Fig. 1), consists of a Schiff base molecule and a water molecule of crystallization. The bond lengths have normal values (Allen et al., 1987), and are comparable to those observed in similar compounds (Nie, 2008; He, 2008; Shi et al., 2007). The dihedral angle between the two aromatic rings is 33.3 (5)°, indicating that the Schiff base molecule is twisted. An intramolecular O—H···N hydrogen bond is observed.

In the crystal structure, the molecules are linked into a two-dimensional network parallel to the (010) by intermolecular N—H···O, O—H···O and C—H···O hydrogen bonds (Table 1).

Related literature top

For related structures, see: Lu et al. (2008a,b,c); Nie (2008); 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 2-hydroxy-3-methoxybenzaldehyde (0.1 mol) and 4-hydroxybenzohydrazide (0.1 mmol) in 95% ethanol (50 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 were obatined by slow evaporation of a 95% ethanol solution at room temperature.

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 a hydrogen bond.
	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'-(2-hydroxy-3-methoxybenzylidene)benzohydrazide monohydrate top

Crystal data top

C₁₅H₁₄N₂O₄·H₂O	F(000) = 320
M_r = 304.30	D_x = 1.379 Mg m⁻³
Monoclinic, Pn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yac	Cell parameters from 623 reflections
a = 4.891 (2) Å	θ = 2.3–24.0°
b = 12.171 (5) Å	µ = 0.11 mm⁻¹
c = 12.371 (5) Å	T = 298 K
β = 95.724 (7)°	Block, colourless
V = 732.8 (5) Å³	0.08 × 0.07 × 0.07 mm
Z = 2

Data collection top

Bruker APEXII CCD area-detector diffractometer	1582 independent reflections
Radiation source: fine-focus sealed tube	791 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.086
ω scans	θ_max = 27.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −6→6
T_min = 0.992, T_max = 0.993	k = −15→15
5972 measured reflections	l = −15→15

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 0.92	w = 1/[σ²(F_o²) + (0.0473P)²] where P = (F_o² + 2F_c²)/3
1582 reflections	(Δ/σ)_max = 0.001
211 parameters	Δρ_max = 0.14 e Å⁻³
6 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₅H₁₄N₂O₄·H₂O	V = 732.8 (5) Å³
M_r = 304.30	Z = 2
Monoclinic, Pn	Mo Kα radiation
a = 4.891 (2) Å	µ = 0.11 mm⁻¹
b = 12.171 (5) Å	T = 298 K
c = 12.371 (5) Å	0.08 × 0.07 × 0.07 mm
β = 95.724 (7)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	1582 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	791 reflections with I > 2σ(I)
T_min = 0.992, T_max = 0.993	R_int = 0.086
5972 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	6 restraints
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 0.92	Δρ_max = 0.14 e Å⁻³
1582 reflections	Δρ_min = −0.15 e Å⁻³
211 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1	0.2886 (8)	0.7446 (3)	0.9901 (3)	0.0588 (11)
H1	0.2167	0.8048	0.9782	0.088*
O2	0.6029 (9)	0.5752 (3)	1.0195 (4)	0.0747 (13)
O3	−0.1590 (7)	1.0380 (3)	0.9939 (3)	0.0564 (10)
O4	−0.9973 (10)	1.3626 (4)	0.7359 (3)	0.0823 (15)
H4	−1.0197	1.3619	0.6694	0.123*
O5	0.3665 (9)	1.0067 (4)	0.0948 (3)	0.0717 (13)
N1	0.1007 (8)	0.9097 (3)	0.8590 (3)	0.0460 (11)
N2	−0.0723 (9)	0.9954 (4)	0.8239 (3)	0.0454 (11)
C1	0.4174 (11)	0.7745 (4)	0.8075 (5)	0.0494 (14)
C2	0.4327 (11)	0.7168 (4)	0.9064 (5)	0.0463 (14)
C3	0.6063 (12)	0.6245 (5)	0.9194 (5)	0.0579 (17)
C4	0.7584 (13)	0.5927 (5)	0.8385 (6)	0.072 (2)
H4A	0.8732	0.5319	0.8484	0.087*
C5	0.7435 (13)	0.6500 (6)	0.7418 (6)	0.073 (2)
H5	0.8484	0.6279	0.6870	0.088*
C6	0.5746 (12)	0.7393 (5)	0.7267 (5)	0.0594 (16)
H6	0.5647	0.7771	0.6611	0.071*
C7	0.2392 (11)	0.8680 (4)	0.7868 (4)	0.0485 (14)
H7	0.2243	0.8993	0.7180	0.058*
C8	−0.2022 (10)	1.0526 (4)	0.8945 (5)	0.0421 (13)
C9	−0.4033 (10)	1.1358 (4)	0.8497 (4)	0.0410 (13)
C10	−0.5053 (12)	1.2129 (5)	0.9167 (5)	0.0589 (16)
H10	−0.4389	1.2138	0.9898	0.071*
C11	−0.6996 (13)	1.2877 (5)	0.8800 (5)	0.0694 (19)
H11	−0.7650	1.3381	0.9277	0.083*
C12	−0.7996 (11)	1.2885 (5)	0.7710 (5)	0.0558 (16)
C13	−0.7035 (13)	1.2128 (5)	0.7021 (5)	0.0655 (18)
H13	−0.7698	1.2125	0.6289	0.079*
C14	−0.5079 (11)	1.1370 (5)	0.7412 (4)	0.0549 (16)
H14	−0.4450	1.0857	0.6938	0.066*
C15	0.8230 (15)	0.4970 (7)	1.0500 (8)	0.107 (3)
H15A	0.7983	0.4329	1.0048	0.160*
H15B	0.8185	0.4763	1.1246	0.160*
H15C	0.9970	0.5302	1.0405	0.160*
H2	−0.076 (13)	1.017 (5)	0.7543 (17)	0.080*
H5A	0.211 (5)	0.997 (5)	0.058 (4)	0.080*
H5B	0.490 (7)	0.992 (5)	0.054 (4)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.063 (3)	0.055 (2)	0.057 (2)	0.014 (2)	0.001 (2)	0.002 (2)
O2	0.071 (3)	0.059 (2)	0.090 (3)	0.024 (2)	−0.013 (3)	0.007 (2)
O3	0.056 (3)	0.081 (3)	0.032 (2)	0.017 (2)	0.0050 (18)	0.007 (2)
O4	0.090 (4)	0.068 (3)	0.086 (3)	0.044 (3)	−0.002 (3)	−0.005 (2)
O5	0.054 (3)	0.122 (4)	0.038 (2)	−0.011 (3)	0.003 (2)	0.005 (2)
N1	0.042 (3)	0.043 (3)	0.051 (3)	0.004 (2)	−0.004 (2)	−0.003 (2)
N2	0.048 (3)	0.050 (3)	0.039 (3)	0.009 (2)	0.007 (2)	0.002 (2)
C1	0.043 (3)	0.046 (3)	0.057 (4)	0.004 (3)	−0.004 (3)	−0.022 (3)
C2	0.041 (4)	0.046 (3)	0.050 (3)	0.001 (3)	−0.001 (3)	−0.014 (3)
C3	0.047 (4)	0.047 (3)	0.076 (5)	0.010 (3)	−0.012 (4)	−0.010 (3)
C4	0.056 (5)	0.063 (4)	0.097 (6)	0.025 (4)	−0.001 (4)	−0.027 (4)
C5	0.052 (4)	0.076 (5)	0.091 (6)	0.011 (4)	0.011 (4)	−0.035 (4)
C6	0.048 (3)	0.065 (4)	0.064 (4)	0.001 (3)	0.000 (3)	−0.017 (3)
C7	0.050 (4)	0.055 (4)	0.041 (3)	0.003 (3)	0.001 (3)	−0.009 (3)
C8	0.034 (3)	0.042 (3)	0.051 (4)	−0.001 (3)	0.003 (3)	−0.005 (3)
C9	0.041 (3)	0.040 (3)	0.042 (3)	0.003 (3)	0.002 (3)	−0.002 (2)
C10	0.065 (4)	0.068 (4)	0.043 (3)	0.009 (4)	−0.001 (3)	−0.007 (3)
C11	0.078 (5)	0.070 (4)	0.059 (5)	0.037 (4)	0.008 (4)	−0.014 (3)
C12	0.052 (4)	0.049 (3)	0.064 (4)	0.017 (3)	−0.004 (3)	−0.001 (3)
C13	0.076 (5)	0.072 (4)	0.047 (4)	0.023 (4)	−0.003 (3)	0.004 (3)
C14	0.057 (4)	0.063 (4)	0.044 (3)	0.025 (3)	0.001 (3)	−0.007 (3)
C15	0.066 (5)	0.088 (5)	0.160 (8)	0.039 (4)	−0.015 (5)	0.028 (5)

Geometric parameters (Å, º) top

O1—C2	1.352 (6)	C4—H4A	0.93
O1—H1	0.82	C5—C6	1.367 (8)
O2—C3	1.377 (7)	C5—H5	0.93
O2—C15	1.459 (7)	C6—H6	0.93
O3—C8	1.240 (6)	C7—H7	0.93
O4—C12	1.361 (6)	C8—C9	1.480 (7)
O4—H4	0.82	C9—C10	1.378 (7)
O5—H5A	0.86 (3)	C9—C14	1.388 (6)
O5—H5B	0.84 (4)	C10—C11	1.361 (7)
N1—C7	1.279 (6)	C10—H10	0.93
N1—N2	1.385 (6)	C11—C12	1.388 (8)
N2—C8	1.328 (6)	C11—H11	0.93
N2—H2	0.90 (3)	C12—C13	1.369 (7)
C1—C6	1.388 (7)	C13—C14	1.381 (7)
C1—C2	1.407 (7)	C13—H13	0.93
C1—C7	1.440 (7)	C14—H14	0.93
C2—C3	1.407 (7)	C15—H15A	0.96
C3—C4	1.362 (8)	C15—H15B	0.96
C4—C5	1.379 (8)	C15—H15C	0.96

C2—O1—H1	109.5	C1—C7—H7	118.5
C3—O2—C15	116.3 (5)	O3—C8—N2	122.1 (5)
C12—O4—H4	109.5	O3—C8—C9	120.7 (5)
H5A—O5—H5B	108 (3)	N2—C8—C9	117.1 (5)
C7—N1—N2	115.5 (4)	C10—C9—C14	117.0 (5)
C8—N2—N1	120.4 (4)	C10—C9—C8	120.5 (5)
C8—N2—H2	121 (4)	C14—C9—C8	122.5 (5)
N1—N2—H2	118 (4)	C11—C10—C9	122.5 (5)
C6—C1—C2	119.2 (5)	C11—C10—H10	118.8
C6—C1—C7	119.0 (6)	C9—C10—H10	118.8
C2—C1—C7	121.8 (5)	C10—C11—C12	119.7 (5)
O1—C2—C3	117.8 (5)	C10—C11—H11	120.2
O1—C2—C1	123.7 (5)	C12—C11—H11	120.2
C3—C2—C1	118.5 (5)	O4—C12—C13	121.6 (5)
C4—C3—O2	126.4 (6)	O4—C12—C11	119.0 (5)
C4—C3—C2	120.7 (6)	C13—C12—C11	119.4 (5)
O2—C3—C2	112.9 (5)	C12—C13—C14	120.0 (6)
C3—C4—C5	120.5 (6)	C12—C13—H13	120.0
C3—C4—H4A	119.7	C14—C13—H13	120.0
C5—C4—H4A	119.7	C13—C14—C9	121.5 (5)
C6—C5—C4	120.0 (6)	C13—C14—H14	119.3
C6—C5—H5	120.0	C9—C14—H14	119.3
C4—C5—H5	120.0	O2—C15—H15A	109.5
C5—C6—C1	121.1 (6)	O2—C15—H15B	109.5
C5—C6—H6	119.4	H15A—C15—H15B	109.5
C1—C6—H6	119.4	O2—C15—H15C	109.5
N1—C7—C1	122.9 (5)	H15A—C15—H15C	109.5
N1—C7—H7	118.5	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	1.99	2.687 (5)	142
N2—H2···O5ⁱ	0.90 (3)	1.99 (3)	2.820 (5)	154 (5)
O4—H4···O2ⁱⁱ	0.82	2.15	2.872 (7)	147
O5—H5A···O3ⁱⁱⁱ	0.86 (3)	1.97 (3)	2.769 (6)	156 (6)
O5—H5B···O3^iv	0.84 (4)	2.01 (3)	2.769 (6)	148 (5)
C7—H7···O5ⁱ	0.93	2.48	3.229 (7)	138
C14—H14···O5ⁱ	0.93	2.34	3.218 (7)	158

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄N₂O₄·H₂O
M_r	304.30
Crystal system, space group	Monoclinic, Pn
Temperature (K)	298
a, b, c (Å)	4.891 (2), 12.171 (5), 12.371 (5)
β (°)	95.724 (7)
V (Å³)	732.8 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.08 × 0.07 × 0.07

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.992, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	5972, 1582, 791
R_int	0.086
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.119, 0.92
No. of reflections	1582
No. of parameters	211
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.15

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	1.99	2.687 (5)	142
N2—H2···O5ⁱ	0.90 (3)	1.99 (3)	2.820 (5)	154 (5)
O4—H4···O2ⁱⁱ	0.82	2.15	2.872 (7)	147
O5—H5A···O3ⁱⁱⁱ	0.86 (3)	1.97 (3)	2.769 (6)	156 (6)
O5—H5B···O3^iv	0.84 (4)	2.01 (3)	2.769 (6)	148 (5)
C7—H7···O5ⁱ	0.93	2.48	3.229 (7)	138
C14—H14···O5ⁱ	0.93	2.34	3.218 (7)	158

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

Acknowledgements

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

References

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Volume 64| Part 10| October 2008| Page o2032

doi:10.1107/S1600536808030894

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

4-Hydr­­oxy-N′-(2-hydr­­oxy-3-meth­oxy­benzyl­­idene)benzohydrazide mono­hydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-Hydroxy-N′-(2-hydroxy-3-methoxybenzylidene)benzohydrazide monohydrate