N′-(4-Hydr­oxy-3-methoxy­benzyl­idene)-4-methoxy­benzohydrazide monohydrate

Lu, J.-F.; Min, S.-T.; Ge, H.-G.; Ji, X.-H.

doi:10.1107/S1600536809034242

organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2301

doi:10.1107/S1600536809034242

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N′-(4-Hydroxy-3-methoxybenzylidene)-4-methoxybenzohydrazide monohydrate

Jiu-Fu Lu,^a ^* Suo-Tian Min,^a Hong-Guang Ge ^a and Xiao-Hui Ji ^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 26 August 2009; accepted 26 August 2009; online 29 August 2009)

In the title compound, C₁₆H₁₆N₂O₄·H₂O, the dihedral angle between the two aromatic rings is 19.6 (2)°. In the crystal structure, molecules are linked into a three-dimensional network by intermolecular N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds.

Related literature

For our previous work in this area, see: Lu et al. (2008a ,b ,c ). For related structures, see: Abdul Alhadi et al. (2009 ); Mohd Lair et al. (2009 ); Narayana et al. (2007 ). For reference bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₆H₁₆N₂O₄·H₂O
M_r = 318.32
Monoclinic, P 2₁ /n
a = 7.942 (1) Å
b = 21.273 (2) Å
c = 10.246 (1) Å
β = 106.596 (2)°
V = 1659.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.32 × 0.30 × 0.30 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.970, T_max = 0.972
9533 measured reflections
3338 independent reflections
2291 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.127
S = 1.04
3338 reflections
220 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯N1ⁱ	0.846 (9)	2.487 (15)	3.1257 (18)	133.0 (17)
O5—H5A⋯O3ⁱ	0.846 (9)	2.107 (13)	2.8927 (18)	154 (2)
O5—H5B⋯O3ⁱⁱ	0.856 (9)	1.884 (10)	2.7401 (17)	179 (2)
N2—H2B⋯O2ⁱ	0.895 (9)	2.185 (12)	3.0398 (18)	159.6 (19)
O2—H2⋯O5ⁱⁱⁱ	0.82	1.77	2.5775 (17)	170
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x, 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/S1600536809034242/hb5071sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809034242/hb5071Isup2.hkl

checkCIF report

Comment top

Schiff bases and their metal complexes have received much attention in recent years. As part of our investigation on the crystal structures of Schiff bases derived from the condensation of aldehydes with benzohydrazides (Lu et al., 2008a,b,c), we report herein the crystal structure of the title new Schiff base compound, (I).

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 (Abdul Alhadi et al., 2009; Mohd Lair et al., 2009; Narayana et al., 2007). The dihedral angle between the two aromatic rings is 19.6 (2)°, indicating that they the molecule is twisted.

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

Related literature top

For own previous work in this area, see: Lu et al. (2008a,b,c). For related structures, see: Abdul Alhadi et al. (2009); Mohd Lair et al. (2009); Narayana et al. (2007). For reference bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was prepared by the Schiff base condensation of 4-hydroxy-3-methoxybenzaldehyde (0.1 mol) and 4-methoxybenzohydrazide (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. Colourless blokcs of (I) 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 (I) showing 30% probability displacement ellipsoids.
	Fig. 2. The crystal packing of (I) viewed along the a axis. Intermolecular hydrogen bonds are drawn by dashed lines. H atoms unrelated to the hydrogen bonding are omitted for clarity.

N'-(4-Hydroxy-3-methoxybenzylidene)-4-methoxybenzohydrazide monohydrate top

Crystal data top

C₁₆H₁₆N₂O₄·H₂O	F(000) = 672
M_r = 318.32	D_x = 1.274 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2203 reflections
a = 7.942 (1) Å	θ = 2.3–24.6°
b = 21.273 (2) Å	µ = 0.10 mm⁻¹
c = 10.246 (1) Å	T = 298 K
β = 106.596 (2)°	Block, colourless
V = 1659.0 (3) Å³	0.32 × 0.30 × 0.30 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3338 independent reflections
Radiation source: fine-focus sealed tube	2291 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ω scans	θ_max = 26.3°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −9→9
T_min = 0.970, T_max = 0.972	k = −26→25
9533 measured reflections	l = −12→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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0586P)² + 0.2417P] where P = (F_o² + 2F_c²)/3
3338 reflections	(Δ/σ)_max = 0.001
220 parameters	Δρ_max = 0.20 e Å⁻³
4 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₆H₁₆N₂O₄·H₂O	V = 1659.0 (3) Å³
M_r = 318.32	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.942 (1) Å	µ = 0.10 mm⁻¹
b = 21.273 (2) Å	T = 298 K
c = 10.246 (1) Å	0.32 × 0.30 × 0.30 mm
β = 106.596 (2)°

Data collection top

Bruker APEXII CCD diffractometer	3338 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	2291 reflections with I > 2σ(I)
T_min = 0.970, T_max = 0.972	R_int = 0.024
9533 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	4 restraints
wR(F²) = 0.127	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.20 e Å⁻³
3338 reflections	Δρ_min = −0.18 e Å⁻³
220 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	0.45414 (18)	0.25435 (6)	−0.34503 (15)	0.0726 (4)
O2	0.25510 (15)	0.15740 (6)	−0.42933 (13)	0.0570 (3)
H2	0.1742	0.1332	−0.4638	0.085*
O3	0.32814 (18)	0.47213 (6)	0.11553 (15)	0.0682 (4)
O4	−0.1311 (2)	0.60007 (7)	0.46039 (15)	0.0791 (4)
O5	0.01680 (17)	0.08043 (6)	0.43784 (15)	0.0612 (4)
N1	0.16872 (18)	0.37019 (6)	−0.01397 (14)	0.0489 (4)
N2	0.10078 (19)	0.40488 (7)	0.07401 (15)	0.0508 (4)
C1	0.1256 (2)	0.28010 (8)	−0.15935 (17)	0.0477 (4)
C2	0.2726 (2)	0.29018 (8)	−0.20479 (17)	0.0487 (4)
H2A	0.3435	0.3251	−0.1744	0.058*
C3	0.3135 (2)	0.24897 (8)	−0.29416 (17)	0.0475 (4)
C4	0.2067 (2)	0.19639 (8)	−0.34092 (17)	0.0456 (4)
C5	0.0626 (2)	0.18616 (9)	−0.29573 (19)	0.0562 (5)
H5	−0.0079	0.1511	−0.3256	0.067*
C6	0.0218 (2)	0.22785 (9)	−0.2059 (2)	0.0600 (5)
H6	−0.0768	0.2207	−0.1762	0.072*
C7	0.5593 (3)	0.30919 (11)	−0.3109 (3)	0.0894 (8)
H7A	0.4872	0.3458	−0.3389	0.134*
H7B	0.6494	0.3084	−0.3565	0.134*
H7C	0.6125	0.3105	−0.2142	0.134*
C8	0.0764 (2)	0.32266 (8)	−0.06566 (18)	0.0512 (4)
H8	−0.0267	0.3149	−0.0425	0.061*
C9	0.1854 (2)	0.45679 (8)	0.13293 (18)	0.0507 (4)
C10	0.1005 (2)	0.49380 (8)	0.21918 (18)	0.0510 (4)
C11	0.1991 (3)	0.53788 (10)	0.3066 (2)	0.0729 (6)
H11	0.3163	0.5435	0.3099	0.087*
C12	0.1273 (3)	0.57418 (10)	0.3899 (2)	0.0757 (6)
H12	0.1966	0.6033	0.4491	0.091*
C13	−0.0457 (3)	0.56687 (9)	0.38450 (19)	0.0602 (5)
C14	−0.1466 (3)	0.52298 (9)	0.2976 (2)	0.0623 (5)
H14	−0.2638	0.5174	0.2945	0.075*
C15	−0.0741 (3)	0.48746 (8)	0.21579 (19)	0.0568 (5)
H15	−0.1440	0.4584	0.1566	0.068*
C16	−0.0366 (4)	0.64796 (11)	0.5474 (2)	0.0959 (8)
H16A	0.0642	0.6299	0.6119	0.144*
H16B	−0.1111	0.6672	0.5951	0.144*
H16C	0.0012	0.6791	0.4941	0.144*
H2B	0.0004 (18)	0.3933 (10)	0.090 (2)	0.080*
H5B	0.064 (2)	0.0464 (7)	0.421 (2)	0.080*
H5A	−0.064 (2)	0.0719 (9)	0.473 (2)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0662 (8)	0.0727 (9)	0.0998 (10)	−0.0254 (7)	0.0572 (8)	−0.0298 (8)
O2	0.0520 (7)	0.0565 (7)	0.0720 (8)	−0.0056 (6)	0.0329 (7)	−0.0161 (6)
O3	0.0697 (9)	0.0606 (8)	0.0880 (10)	−0.0194 (7)	0.0443 (8)	−0.0096 (7)
O4	0.1010 (11)	0.0712 (9)	0.0694 (9)	0.0105 (8)	0.0311 (8)	−0.0178 (8)
O5	0.0558 (8)	0.0502 (7)	0.0862 (10)	−0.0013 (6)	0.0342 (7)	−0.0118 (7)
N1	0.0522 (8)	0.0479 (8)	0.0549 (8)	−0.0001 (7)	0.0285 (7)	−0.0016 (7)
N2	0.0560 (9)	0.0487 (8)	0.0582 (9)	−0.0065 (7)	0.0329 (7)	−0.0072 (7)
C1	0.0480 (9)	0.0491 (9)	0.0524 (10)	−0.0014 (7)	0.0249 (8)	−0.0019 (8)
C2	0.0498 (10)	0.0460 (9)	0.0557 (10)	−0.0071 (8)	0.0241 (8)	−0.0036 (8)
C3	0.0423 (9)	0.0515 (9)	0.0561 (10)	−0.0040 (7)	0.0259 (8)	−0.0023 (8)
C4	0.0455 (9)	0.0455 (9)	0.0509 (10)	0.0010 (7)	0.0219 (8)	−0.0026 (7)
C5	0.0515 (10)	0.0550 (10)	0.0704 (12)	−0.0125 (8)	0.0307 (9)	−0.0129 (9)
C6	0.0529 (11)	0.0630 (11)	0.0772 (13)	−0.0131 (9)	0.0397 (10)	−0.0128 (10)
C7	0.0736 (14)	0.0922 (16)	0.125 (2)	−0.0380 (13)	0.0656 (15)	−0.0365 (15)
C8	0.0509 (10)	0.0531 (10)	0.0587 (11)	−0.0051 (8)	0.0304 (8)	−0.0027 (8)
C9	0.0588 (11)	0.0451 (9)	0.0536 (10)	−0.0068 (8)	0.0247 (8)	0.0040 (8)
C10	0.0649 (11)	0.0415 (9)	0.0511 (10)	−0.0042 (8)	0.0238 (9)	0.0016 (8)
C11	0.0790 (14)	0.0676 (13)	0.0817 (14)	−0.0244 (11)	0.0383 (12)	−0.0179 (11)
C12	0.0937 (17)	0.0644 (13)	0.0748 (14)	−0.0245 (12)	0.0335 (12)	−0.0234 (11)
C13	0.0831 (14)	0.0490 (10)	0.0522 (11)	0.0069 (10)	0.0252 (10)	−0.0008 (8)
C14	0.0600 (12)	0.0637 (12)	0.0634 (12)	0.0082 (9)	0.0179 (10)	−0.0075 (10)
C15	0.0593 (11)	0.0528 (10)	0.0574 (11)	0.0019 (8)	0.0151 (9)	−0.0089 (9)
C16	0.136 (2)	0.0756 (14)	0.0731 (15)	0.0114 (15)	0.0258 (15)	−0.0260 (13)

Geometric parameters (Å, º) top

O1—C3	1.3654 (19)	C5—H5	0.9300
O1—C7	1.419 (2)	C6—H6	0.9300
O2—C4	1.3622 (19)	C7—H7A	0.9600
O2—H2	0.8200	C7—H7B	0.9600
O3—C9	1.241 (2)	C7—H7C	0.9600
O4—C13	1.365 (2)	C8—H8	0.9300
O4—C16	1.419 (3)	C9—C10	1.482 (2)
O5—H5B	0.856 (9)	C10—C11	1.376 (3)
O5—H5A	0.846 (9)	C10—C15	1.384 (3)
N1—C8	1.272 (2)	C11—C12	1.388 (3)
N1—N2	1.3878 (18)	C11—H11	0.9300
N2—C9	1.343 (2)	C12—C13	1.369 (3)
N2—H2B	0.895 (9)	C12—H12	0.9300
C1—C6	1.385 (2)	C13—C14	1.378 (3)
C1—C2	1.391 (2)	C14—C15	1.372 (2)
C1—C8	1.452 (2)	C14—H14	0.9300
C2—C3	1.372 (2)	C15—H15	0.9300
C2—H2A	0.9300	C16—H16A	0.9600
C3—C4	1.403 (2)	C16—H16B	0.9600
C4—C5	1.369 (2)	C16—H16C	0.9600
C5—C6	1.382 (2)

C3—O1—C7	117.57 (14)	H7B—C7—H7C	109.5
C4—O2—H2	109.5	N1—C8—C1	122.59 (15)
C13—O4—C16	117.99 (19)	N1—C8—H8	118.7
H5B—O5—H5A	109.9 (17)	C1—C8—H8	118.7
C8—N1—N2	114.08 (13)	O3—C9—N2	120.79 (16)
C9—N2—N1	119.46 (14)	O3—C9—C10	122.43 (15)
C9—N2—H2B	120.1 (14)	N2—C9—C10	116.78 (15)
N1—N2—H2B	120.5 (14)	C11—C10—C15	117.57 (17)
C6—C1—C2	118.84 (15)	C11—C10—C9	118.60 (17)
C6—C1—C8	118.80 (15)	C15—C10—C9	123.83 (16)
C2—C1—C8	122.36 (15)	C10—C11—C12	121.5 (2)
C3—C2—C1	120.41 (15)	C10—C11—H11	119.3
C3—C2—H2A	119.8	C12—C11—H11	119.3
C1—C2—H2A	119.8	C13—C12—C11	119.72 (19)
O1—C3—C2	125.22 (15)	C13—C12—H12	120.1
O1—C3—C4	114.67 (14)	C11—C12—H12	120.1
C2—C3—C4	120.11 (14)	O4—C13—C12	125.08 (18)
O2—C4—C5	123.37 (15)	O4—C13—C14	115.25 (19)
O2—C4—C3	117.03 (14)	C12—C13—C14	119.67 (18)
C5—C4—C3	119.59 (15)	C15—C14—C13	120.01 (19)
C4—C5—C6	120.06 (16)	C15—C14—H14	120.0
C4—C5—H5	120.0	C13—C14—H14	120.0
C6—C5—H5	120.0	C14—C15—C10	121.56 (17)
C5—C6—C1	120.98 (16)	C14—C15—H15	119.2
C5—C6—H6	119.5	C10—C15—H15	119.2
C1—C6—H6	119.5	O4—C16—H16A	109.5
O1—C7—H7A	109.5	O4—C16—H16B	109.5
O1—C7—H7B	109.5	H16A—C16—H16B	109.5
H7A—C7—H7B	109.5	O4—C16—H16C	109.5
O1—C7—H7C	109.5	H16A—C16—H16C	109.5
H7A—C7—H7C	109.5	H16B—C16—H16C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···N1ⁱ	0.85 (1)	2.49 (2)	3.1257 (18)	133 (2)
O5—H5A···O3ⁱ	0.85 (1)	2.11 (1)	2.8927 (18)	154 (2)
O5—H5B···O3ⁱⁱ	0.86 (1)	1.88 (1)	2.7401 (17)	179 (2)
N2—H2B···O2ⁱ	0.90 (1)	2.19 (1)	3.0398 (18)	160 (2)
O2—H2···O5ⁱⁱⁱ	0.82	1.77	2.5775 (17)	170

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆N₂O₄·H₂O
M_r	318.32
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	7.942 (1), 21.273 (2), 10.246 (1)
β (°)	106.596 (2)
V (Å³)	1659.0 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.32 × 0.30 × 0.30

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.970, 0.972
No. of measured, independent and observed [I > 2σ(I)] reflections	9533, 3338, 2291
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.623

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.127, 1.04
No. of reflections	3338
No. of parameters	220
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.18

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
O5—H5A···N1ⁱ	0.846 (9)	2.487 (15)	3.1257 (18)	133.0 (17)
O5—H5A···O3ⁱ	0.846 (9)	2.107 (13)	2.8927 (18)	154 (2)
O5—H5B···O3ⁱⁱ	0.856 (9)	1.884 (10)	2.7401 (17)	179 (2)
N2—H2B···O2ⁱ	0.895 (9)	2.185 (12)	3.0398 (18)	159.6 (19)
O2—H2···O5ⁱⁱⁱ	0.82	1.77	2.5775 (17)	170

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

Acknowledgements

The authors acknowledge the Scientific Research Foundation of Shaanxi University of Technology (Project No. SLGQD0708).

References

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