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

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

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 15 December 2008; accepted 16 December 2008; online 20 December 2008)

The Schiff base mol­ecule of the title compound, C15H14N2O4·H2O, adopts a trans configuration with respect to the C=N double bond; the Schiff base itself is almost planar (r.m.s. deviation for all non-H atoms = 0.040 Å). The amido N atom is the hydrogen-bond donor to the water mol­ecule, which is the hydrogen-bond donor to the hydr­oxy groups of two neighboring mol­ecules. One of the hydroxyl groups acts as an intra­molecular and the other as an inter­molecular hydrogen-bond donor.

Related literature

For the structure of (E)-4-chloro-N′-(2-hydr­oxy-3-methoxy­benzyl­idene)benzo­hydrazide, which crystallizes as a monohydrate, see: Cui et al. (2007[Cui, J., Yin, H. & Qiao, Y. (2007). Acta Cryst. E63, o3548.]). For a series of similar compounds, see: Lu et al. (2008a[Lu, J.-F., Min, S.-T., Ji, X.-H. & Dang, Z.-H. (2008a). Acta Cryst. E64, o1693.],b[Lu, J.-F., Min, S.-T., Ji, X.-H. & Dang, Z.-H. (2008b). Acta Cryst. E64, o1694.],c[Lu, J.-F., Min, S.-T., Ji, X.-H. & Dang, Z.-H. (2008c). Acta Cryst. E64, o1695.]). For this and other compounds with anti­malarial properties, see: Melnyk et al. (2006[Melnyk, P., Leroux, V., Sergheraert, C. & Grellier, P. (2006). Bioorg. & Med. Chem. Lett. 16, 31-35.]).

[Scheme 1]

Experimental

Crystal data
  • C15H14N2O4·H2O

  • Mr = 304.30

  • Monoclinic, P 21 /n

  • a = 7.1763 (2) Å

  • b = 16.6507 (5) Å

  • c = 12.1828 (4) Å

  • β = 98.022 (2)°

  • V = 1441.48 (8) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.11 mm−1

  • T = 100 (2) K

  • 0.16 × 0.04 × 0.04 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: none

  • 13327 measured reflections

  • 3315 independent reflections

  • 1903 reflections with I > 2σ(I)

  • Rint = 0.053

Refinement
  • R[F2 > 2σ(F2)] = 0.060

  • wR(F2) = 0.180

  • S = 1.05

  • 3315 reflections

  • 200 parameters

  • H-atom parameters constrained

  • Δρmax = 0.66 e Å−3

  • Δρmin = −0.43 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯O2i 0.84 1.86 2.621 (3) 150
O3—H3⋯N2 0.84 1.94 2.575 (3) 132
O5—H51⋯O1ii 0.84 2.03 2.833 (3) 160
O5—H52⋯O3iii 0.84 2.27 3.070 (4) 160
N1—H11⋯O5 0.88 2.05 2.883 (3) 158
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) -x+1, -y+1, -z+2; (iii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


Related literature top

For (E)-4-chloro-N'-(2-hydroxy-3-methoxybenzylidene)benzohydrazide, which crystallizes as a monohydrate, see: Cui et al. (2007). For a set of similar compounds, see: Lu et al. (2008a,b,c). For compounds with antimalarial properties, see: Melnyk et al. (2006).

Experimental top

2-Hydroxy-3-methoxybenzaldehyde (0.30 g, 2 mmol) and 4-hydroxybenzohydrazide (0.30 g, 2 mmol) were heated in an ethanol-methanol mixture (50 ml) for 2 h. The solvent was removed and the resulting compound recrystallized from ethanol.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95–0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5U(C). The oxygen- and nitrogen-bound ones were located in a difference Fourier map, and were refined with distance restraints (O–H 0.84±0.01, N–H 0.88±0.01 Å); their isotropic displacement parameters were freely refined.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of C15H14N2O4.H2O at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
(E)-4-Hydroxy-N'-(2-hydroxy-4-methoxybenzylidene)benzohydrazide monohydrate top
Crystal data top
C15H14N2O4·H2OF(000) = 640
Mr = 304.30Dx = 1.402 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1918 reflections
a = 7.1763 (2) Åθ = 2.4–27.3°
b = 16.6507 (5) ŵ = 0.11 mm1
c = 12.1828 (4) ÅT = 100 K
β = 98.022 (2)°Prism, yellow
V = 1441.48 (8) Å30.16 × 0.04 × 0.04 mm
Z = 4
Data collection top
Bruker SMART APEX
diffractometer
1903 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.053
Graphite monochromatorθmax = 27.5°, θmin = 2.1°
ω scansh = 99
13327 measured reflectionsk = 2121
3315 independent reflectionsl = 1515
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.180H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0687P)2 + 1.4764P]
where P = (Fo2 + 2Fc2)/3
3315 reflections(Δ/σ)max = 0.001
200 parametersΔρmax = 0.66 e Å3
0 restraintsΔρmin = 0.43 e Å3
Crystal data top
C15H14N2O4·H2OV = 1441.48 (8) Å3
Mr = 304.30Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.1763 (2) ŵ = 0.11 mm1
b = 16.6507 (5) ÅT = 100 K
c = 12.1828 (4) Å0.16 × 0.04 × 0.04 mm
β = 98.022 (2)°
Data collection top
Bruker SMART APEX
diffractometer
1903 reflections with I > 2σ(I)
13327 measured reflectionsRint = 0.053
3315 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0600 restraints
wR(F2) = 0.180H-atom parameters constrained
S = 1.05Δρmax = 0.66 e Å3
3315 reflectionsΔρmin = 0.43 e Å3
200 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.7450 (3)0.31702 (12)1.09538 (15)0.0271 (5)
H10.77450.26981.11500.041*
O20.3884 (3)0.32742 (11)0.58919 (15)0.0246 (5)
O30.1758 (3)0.41831 (13)0.32215 (18)0.0444 (6)
H30.22620.40670.38660.067*
O40.1014 (3)0.59721 (14)0.05179 (16)0.0359 (6)
O50.4249 (4)0.61425 (14)0.73043 (18)0.0495 (7)
H510.40270.63630.78920.074*
H520.54200.61080.73170.074*
N10.3620 (3)0.45875 (14)0.62786 (18)0.0208 (5)
H110.38000.49870.67540.025*
N20.2800 (3)0.47111 (14)0.51985 (17)0.0218 (5)
C10.4997 (3)0.36829 (15)0.7739 (2)0.0174 (5)
C20.5351 (4)0.42869 (16)0.8536 (2)0.0204 (6)
H20.50120.48260.83450.024*
C30.6192 (4)0.41082 (16)0.9602 (2)0.0216 (6)
H3A0.64490.45241.01350.026*
C40.6653 (3)0.33229 (16)0.9886 (2)0.0197 (6)
C50.6322 (4)0.27144 (16)0.9108 (2)0.0214 (6)
H5A0.66550.21760.93050.026*
C60.5504 (4)0.28976 (16)0.8043 (2)0.0208 (6)
H60.52840.24810.75080.025*
C70.4134 (3)0.38292 (16)0.6579 (2)0.0191 (6)
C80.2221 (4)0.54217 (18)0.4913 (2)0.0231 (6)
H80.23620.58480.54360.028*
C90.1350 (4)0.55631 (18)0.3780 (2)0.0235 (6)
C100.1117 (4)0.49462 (18)0.2982 (2)0.0289 (7)
C110.0295 (4)0.5107 (2)0.1905 (2)0.0329 (7)
H11A0.01250.46890.13710.040*
C120.0278 (4)0.5882 (2)0.1614 (2)0.0281 (7)
C130.0097 (4)0.64983 (19)0.2380 (2)0.0290 (7)
H130.05190.70250.21770.035*
C140.0714 (4)0.63284 (18)0.3450 (2)0.0270 (6)
H140.08430.67490.39820.032*
C150.1581 (4)0.6759 (2)0.0151 (3)0.0385 (8)
H15A0.20260.67490.06470.058*
H15B0.05080.71270.02990.058*
H15C0.25980.69440.05490.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0379 (11)0.0266 (11)0.0146 (9)0.0096 (9)0.0039 (8)0.0015 (8)
O20.0309 (10)0.0230 (10)0.0188 (10)0.0048 (8)0.0008 (8)0.0005 (8)
O30.0701 (17)0.0318 (13)0.0264 (12)0.0012 (12)0.0107 (11)0.0029 (10)
O40.0320 (12)0.0538 (15)0.0203 (10)0.0041 (10)0.0018 (9)0.0118 (10)
O50.0772 (18)0.0431 (14)0.0259 (12)0.0265 (13)0.0009 (12)0.0119 (11)
N10.0228 (12)0.0233 (12)0.0152 (11)0.0005 (9)0.0016 (9)0.0003 (9)
N20.0209 (11)0.0306 (13)0.0132 (11)0.0014 (10)0.0004 (9)0.0039 (9)
C10.0136 (12)0.0223 (13)0.0164 (13)0.0033 (10)0.0020 (10)0.0001 (11)
C20.0201 (13)0.0213 (14)0.0197 (13)0.0023 (10)0.0027 (10)0.0031 (11)
C30.0260 (14)0.0207 (14)0.0172 (13)0.0012 (11)0.0001 (10)0.0035 (11)
C40.0192 (13)0.0249 (14)0.0144 (12)0.0032 (11)0.0007 (10)0.0034 (11)
C50.0221 (13)0.0201 (14)0.0214 (13)0.0022 (11)0.0006 (11)0.0011 (11)
C60.0217 (13)0.0228 (14)0.0170 (13)0.0005 (11)0.0004 (11)0.0033 (11)
C70.0173 (13)0.0225 (14)0.0176 (13)0.0027 (10)0.0029 (10)0.0000 (11)
C80.0197 (13)0.0303 (15)0.0195 (14)0.0004 (11)0.0035 (11)0.0013 (12)
C90.0184 (13)0.0327 (16)0.0198 (14)0.0033 (11)0.0043 (11)0.0066 (12)
C100.0333 (16)0.0286 (16)0.0242 (14)0.0018 (13)0.0013 (12)0.0074 (13)
C110.0371 (17)0.0391 (18)0.0211 (15)0.0053 (14)0.0013 (12)0.0008 (13)
C120.0192 (14)0.0471 (19)0.0177 (14)0.0008 (13)0.0011 (11)0.0108 (13)
C130.0237 (14)0.0358 (17)0.0269 (16)0.0055 (12)0.0018 (12)0.0123 (13)
C140.0235 (14)0.0327 (16)0.0249 (15)0.0039 (12)0.0043 (12)0.0033 (12)
C150.0314 (17)0.057 (2)0.0263 (16)0.0062 (16)0.0018 (13)0.0173 (16)
Geometric parameters (Å, º) top
O1—C41.370 (3)C3—H3A0.9500
O1—H10.8400C4—C51.385 (4)
O2—C71.243 (3)C5—C61.382 (4)
O3—C101.369 (4)C5—H5A0.9500
O3—H30.8400C6—H60.9500
O4—C121.374 (3)C8—C91.452 (4)
O4—C151.426 (4)C8—H80.9500
O5—H510.8400C9—C141.394 (4)
O5—H520.8400C9—C101.408 (4)
N1—C71.351 (3)C10—C111.387 (4)
N1—N21.380 (3)C11—C121.385 (4)
N1—H110.8800C11—H11A0.9500
N2—C81.286 (4)C12—C131.381 (4)
C1—C61.393 (4)C13—C141.381 (4)
C1—C21.396 (4)C13—H130.9500
C1—C71.482 (3)C14—H140.9500
C2—C31.386 (4)C15—H15A0.9800
C2—H20.9500C15—H15B0.9800
C3—C41.381 (4)C15—H15C0.9800
C4—O1—H1119.9N1—C7—C1118.3 (2)
C10—O3—H3120.0N2—C8—C9119.1 (3)
C12—O4—C15117.3 (3)N2—C8—H8120.5
H51—O5—H52108.8C9—C8—H8120.5
C7—N1—N2117.5 (2)C14—C9—C10117.7 (3)
C7—N1—H11121.3C14—C9—C8120.2 (3)
N2—N1—H11121.3C10—C9—C8122.1 (3)
C8—N2—N1118.3 (2)O3—C10—C11117.8 (3)
C6—C1—C2118.4 (2)O3—C10—C9121.7 (3)
C6—C1—C7117.8 (2)C11—C10—C9120.4 (3)
C2—C1—C7123.8 (2)C12—C11—C10119.6 (3)
C3—C2—C1120.7 (2)C12—C11—H11A120.2
C3—C2—H2119.7C10—C11—H11A120.2
C1—C2—H2119.7O4—C12—C13124.3 (3)
C4—C3—C2119.8 (2)O4—C12—C11114.2 (3)
C4—C3—H3A120.1C13—C12—C11121.5 (3)
C2—C3—H3A120.1C12—C13—C14118.3 (3)
O1—C4—C3117.9 (2)C12—C13—H13120.9
O1—C4—C5121.5 (2)C14—C13—H13120.9
C3—C4—C5120.5 (2)C13—C14—C9122.5 (3)
C6—C5—C4119.4 (2)C13—C14—H14118.7
C6—C5—H5A120.3C9—C14—H14118.7
C4—C5—H5A120.3O4—C15—H15A109.5
C5—C6—C1121.2 (2)O4—C15—H15B109.5
C5—C6—H6119.4H15A—C15—H15B109.5
C1—C6—H6119.4O4—C15—H15C109.5
O2—C7—N1120.3 (2)H15A—C15—H15C109.5
O2—C7—C1121.4 (2)H15B—C15—H15C109.5
C7—N1—N2—C8176.8 (2)N2—C8—C9—C14179.9 (3)
C6—C1—C2—C30.2 (4)N2—C8—C9—C100.0 (4)
C7—C1—C2—C3178.9 (2)C14—C9—C10—O3177.7 (3)
C1—C2—C3—C41.2 (4)C8—C9—C10—O32.2 (4)
C2—C3—C4—O1178.8 (2)C14—C9—C10—C110.6 (4)
C2—C3—C4—C51.5 (4)C8—C9—C10—C11179.3 (3)
O1—C4—C5—C6179.6 (2)O3—C10—C11—C12176.4 (3)
C3—C4—C5—C60.7 (4)C9—C10—C11—C120.8 (4)
C4—C5—C6—C10.3 (4)C15—O4—C12—C131.6 (4)
C2—C1—C6—C50.6 (4)C15—O4—C12—C11178.2 (3)
C7—C1—C6—C5179.7 (2)C10—C11—C12—O4178.0 (3)
N2—N1—C7—O20.7 (4)C10—C11—C12—C131.8 (4)
N2—N1—C7—C1179.3 (2)O4—C12—C13—C14178.4 (3)
C6—C1—C7—O20.7 (4)C11—C12—C13—C141.4 (4)
C2—C1—C7—O2178.4 (2)C12—C13—C14—C90.0 (4)
C6—C1—C7—N1179.3 (2)C10—C9—C14—C131.0 (4)
C2—C1—C7—N11.6 (4)C8—C9—C14—C13178.9 (3)
N1—N2—C8—C9179.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.841.862.621 (3)150
O3—H3···N20.841.942.575 (3)132
O5—H51···O1ii0.842.032.833 (3)160
O5—H52···O3iii0.842.273.070 (4)160
N1—H11···O50.882.052.883 (3)158
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x+1, y+1, z+2; (iii) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC15H14N2O4·H2O
Mr304.30
Crystal system, space groupMonoclinic, P21/n
Temperature (K)100
a, b, c (Å)7.1763 (2), 16.6507 (5), 12.1828 (4)
β (°) 98.022 (2)
V3)1441.48 (8)
Z4
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.16 × 0.04 × 0.04
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
13327, 3315, 1903
Rint0.053
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.060, 0.180, 1.05
No. of reflections3315
No. of parameters200
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.66, 0.43

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.841.862.621 (3)150
O3—H3···N20.841.942.575 (3)132
O5—H51···O1ii0.842.032.833 (3)160
O5—H52···O3iii0.842.273.070 (4)160
N1—H11···O50.882.052.883 (3)158
Symmetry codes: (i) x+1/2, y+1/2, z+1/2; (ii) x+1, y+1, z+2; (iii) x+1, y+1, z+1.
 

Acknowledgements

We thank the University of Malaya for funding this study (Science Fund grants 12–02-03–2031, 12–02-03–2051).

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS
First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationCui, J., Yin, H. & Qiao, Y. (2007). Acta Cryst. E63, o3548.  Web of Science CSD CrossRef IUCr Journals
First citationLu, J.-F., Min, S.-T., Ji, X.-H. & Dang, Z.-H. (2008a). Acta Cryst. E64, o1693.  Web of Science CSD CrossRef IUCr Journals
First citationLu, J.-F., Min, S.-T., Ji, X.-H. & Dang, Z.-H. (2008b). Acta Cryst. E64, o1694.  Web of Science CSD CrossRef IUCr Journals
First citationLu, J.-F., Min, S.-T., Ji, X.-H. & Dang, Z.-H. (2008c). Acta Cryst. E64, o1695.  Web of Science CSD CrossRef IUCr Journals
First citationMelnyk, P., Leroux, V., Sergheraert, C. & Grellier, P. (2006). Bioorg. & Med. Chem. Lett. 16, 31–35.  Web of Science CrossRef CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationWestrip, S. P. (2009). publCIF. In preparation.

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