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Acta Crystallogr Sect E Struct Rep Online. 2009 January 1; 65(Pt 1): o190.
Published online 2008 December 20. doi:  10.1107/S160053680804289X
PMCID: PMC2968098

(E)-4-Hydr­oxy-N′-(2-hydr­oxy-4-methoxy­benzyl­idene)benzohydrazide N,N-dimethyl­formamide solvate

Abstract

The Schiff base mol­ecule of the title compound, C15H14N2O4·C3H7NO, adopts a trans configuration with respect to the C=N double bond; the Schiff base itself is nearly planar (r.m.s. deviation 0.20 Å). The amido N atom is a hydrogen-bond donor to the dimethyl­formamide solvate mol­ecule. One of the hydr­oxy groups forms an intra­molecular hydrogen bond to the N atom of the C=N double bond, whereas the other forms an inter­molecular hydrogen bond to the carbonyl group.

Related literature

For the corresponding monohydrate, see: Lair et al. (2009 [triangle]).

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Object name is e-65-0o190-scheme1.jpg

Experimental

Crystal data

  • C15H14N2O4·C3H7NO
  • M r = 359.38
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o190-efi1.jpg
  • a = 11.8273 (2) Å
  • b = 7.8206 (2) Å
  • c = 19.4218 (3) Å
  • β = 103.674 (1)°
  • V = 1745.53 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 100 (2) K
  • 0.30 × 0.25 × 0.15 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: none
  • 11825 measured reflections
  • 4003 independent reflections
  • 3303 reflections with I > 2σ(I)
  • R int = 0.023

Refinement

  • R[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.104
  • S = 1.01
  • 4003 reflections
  • 240 parameters
  • H-atom parameters constrained
  • Δρmax = 0.29 e Å−3
  • Δρmin = −0.22 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680804289X/bt2837sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680804289X/bt2837Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Experimental

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 hours. The solvent was removed and the resulting compound recrystallized from DMF.

Refinement

Hydrogen atoms were placed at calculated positions (C–H 0.95–0.98, N–H 0.88, O–H 0.84 Å) and were treated as riding on their parent carbon atoms, with U(H) set to 1.2–1.5 times Ueq(C,N,O).

Figures

Fig. 1.
Displacement ellipsoid plot (Barbour, 2001) of the title compound at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
Fig. 2.
Packing diagram with hydrogen bonds drawn as dashed lines.

Crystal data

C15H14N2O4·C3H7NOF(000) = 760
Mr = 359.38Dx = 1.368 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4180 reflections
a = 11.8273 (2) Åθ = 2.2–28.3°
b = 7.8206 (2) ŵ = 0.10 mm1
c = 19.4218 (3) ÅT = 100 K
β = 103.674 (1)°Prism, colorless
V = 1745.53 (6) Å30.30 × 0.25 × 0.15 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer3303 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
graphiteθmax = 27.5°, θmin = 2.2°
ω scansh = −15→14
11825 measured reflectionsk = −10→8
4003 independent reflectionsl = −25→25

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.0515P)2 + 0.678P] where P = (Fo2 + 2Fc2)/3
4003 reflections(Δ/σ)max = 0.001
240 parametersΔρmax = 0.29 e Å3
0 restraintsΔρmin = −0.22 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O10.66809 (8)0.74503 (12)0.66928 (5)0.0199 (2)
H1O0.69790.76760.71200.030*
O20.22303 (8)0.32357 (12)0.69867 (4)0.0211 (2)
O3−0.04810 (8)0.04690 (13)0.62396 (5)0.0228 (2)
H3O0.00690.11610.62590.034*
O4−0.40063 (8)−0.13116 (12)0.47806 (5)0.0200 (2)
O50.18144 (8)0.46309 (12)0.44318 (5)0.0227 (2)
N10.17427 (9)0.37007 (14)0.58062 (5)0.0170 (2)
H1N0.18880.42170.54340.020*
N20.07635 (9)0.27015 (14)0.57472 (5)0.0173 (2)
N30.16184 (11)0.57465 (17)0.33359 (6)0.0285 (3)
C10.35639 (10)0.48355 (16)0.64886 (6)0.0154 (2)
C20.41943 (11)0.53743 (17)0.71534 (6)0.0188 (3)
H20.39010.51460.75590.023*
C30.52370 (11)0.62336 (17)0.72326 (7)0.0197 (3)
H30.56560.65840.76900.024*
C40.56747 (11)0.65871 (16)0.66420 (6)0.0164 (3)
C50.50566 (11)0.60607 (16)0.59728 (6)0.0179 (3)
H50.53510.62970.55680.022*
C60.40136 (11)0.51936 (16)0.58983 (6)0.0174 (3)
H60.35970.48370.54410.021*
C70.24710 (11)0.38628 (16)0.64518 (6)0.0162 (2)
C80.00648 (11)0.25971 (16)0.51315 (6)0.0170 (3)
H80.02280.32010.47420.020*
C9−0.09720 (10)0.15539 (16)0.50355 (6)0.0158 (2)
C10−0.12163 (11)0.05447 (16)0.55883 (6)0.0169 (3)
C11−0.22325 (11)−0.04046 (16)0.54772 (6)0.0178 (3)
H11−0.2388−0.10900.58480.021*
C12−0.30237 (11)−0.03528 (16)0.48223 (7)0.0169 (3)
C13−0.28026 (11)0.06116 (16)0.42650 (7)0.0183 (3)
H13−0.33410.06330.38170.022*
C14−0.17781 (11)0.15370 (16)0.43817 (6)0.0173 (3)
H14−0.16170.21860.40020.021*
C15−0.49470 (11)−0.10776 (18)0.41743 (7)0.0208 (3)
H15A−0.5643−0.16510.42520.031*
H15B−0.4739−0.15680.37570.031*
H15C−0.51050.01470.40980.031*
C160.21144 (11)0.56143 (17)0.40187 (7)0.0217 (3)
H160.27570.63430.42040.026*
C170.06495 (16)0.4656 (3)0.30112 (9)0.0449 (5)
H17A0.05020.38390.33620.067*
H17B0.08360.40330.26140.067*
H17C−0.00450.53580.28370.067*
C180.20628 (17)0.6926 (3)0.28847 (10)0.0555 (6)
H18A0.27250.75580.31700.083*
H18B0.14480.77310.26650.083*
H18C0.23150.62830.25140.083*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0186 (4)0.0259 (5)0.0151 (4)−0.0060 (4)0.0037 (3)−0.0012 (4)
O20.0185 (4)0.0274 (5)0.0168 (4)−0.0028 (4)0.0030 (3)0.0036 (4)
O30.0202 (5)0.0306 (6)0.0156 (4)−0.0057 (4)0.0005 (4)0.0032 (4)
O40.0167 (4)0.0236 (5)0.0188 (4)−0.0051 (4)0.0026 (4)0.0005 (4)
O50.0268 (5)0.0235 (5)0.0173 (4)−0.0020 (4)0.0044 (4)0.0008 (4)
N10.0158 (5)0.0190 (5)0.0155 (5)−0.0034 (4)0.0023 (4)0.0013 (4)
N20.0149 (5)0.0180 (5)0.0191 (5)−0.0012 (4)0.0040 (4)−0.0011 (4)
N30.0272 (6)0.0369 (7)0.0224 (6)0.0071 (5)0.0079 (5)0.0088 (5)
C10.0155 (6)0.0138 (6)0.0166 (6)0.0017 (5)0.0027 (5)0.0003 (4)
C20.0213 (6)0.0210 (7)0.0146 (6)−0.0028 (5)0.0054 (5)−0.0002 (5)
C30.0224 (6)0.0220 (7)0.0140 (6)−0.0037 (5)0.0031 (5)−0.0019 (5)
C40.0156 (6)0.0152 (6)0.0180 (6)0.0003 (5)0.0033 (5)0.0004 (5)
C50.0196 (6)0.0196 (6)0.0155 (6)0.0004 (5)0.0058 (5)0.0003 (5)
C60.0183 (6)0.0188 (6)0.0138 (6)0.0009 (5)0.0013 (5)−0.0008 (5)
C70.0157 (6)0.0159 (6)0.0168 (6)0.0021 (5)0.0032 (5)−0.0002 (5)
C80.0178 (6)0.0168 (6)0.0168 (6)0.0008 (5)0.0050 (5)0.0004 (5)
C90.0146 (6)0.0156 (6)0.0173 (6)0.0011 (5)0.0041 (5)−0.0013 (5)
C100.0167 (6)0.0190 (6)0.0145 (6)0.0024 (5)0.0028 (5)−0.0008 (5)
C110.0195 (6)0.0189 (6)0.0161 (6)0.0009 (5)0.0064 (5)0.0018 (5)
C120.0151 (6)0.0160 (6)0.0203 (6)−0.0003 (5)0.0055 (5)−0.0027 (5)
C130.0173 (6)0.0210 (7)0.0156 (6)0.0012 (5)0.0016 (5)−0.0002 (5)
C140.0189 (6)0.0179 (6)0.0151 (6)0.0012 (5)0.0042 (5)0.0022 (5)
C150.0163 (6)0.0252 (7)0.0198 (6)−0.0030 (5)0.0022 (5)−0.0017 (5)
C160.0197 (6)0.0211 (7)0.0239 (6)0.0011 (5)0.0045 (5)0.0008 (5)
C170.0402 (10)0.0651 (13)0.0238 (8)0.0006 (9)−0.0040 (7)−0.0066 (8)
C180.0496 (11)0.0763 (15)0.0460 (11)0.0161 (10)0.0217 (9)0.0405 (10)

Geometric parameters (Å, °)

O1—C41.3514 (15)C5—H50.9500
O1—H1O0.8400C6—H60.9500
O2—C71.2412 (15)C8—C91.4478 (17)
O3—C101.3565 (15)C8—H80.9500
O3—H3O0.8400C9—C141.3962 (17)
O4—C121.3693 (15)C9—C101.4162 (17)
O4—C151.4278 (15)C10—C111.3855 (17)
O5—C161.2229 (16)C11—C121.3901 (17)
N1—C71.3489 (15)C11—H110.9500
N1—N21.3791 (14)C12—C131.3938 (17)
N1—H1N0.8800C13—C141.3832 (17)
N2—C81.2855 (16)C13—H130.9500
N3—C161.3212 (17)C14—H140.9500
N3—C171.448 (2)C15—H15A0.9800
N3—C181.454 (2)C15—H15B0.9800
C1—C21.3948 (17)C15—H15C0.9800
C1—C61.4013 (17)C16—H160.9500
C1—C71.4870 (17)C17—H17A0.9800
C2—C31.3808 (18)C17—H17B0.9800
C2—H20.9500C17—H17C0.9800
C3—C41.3931 (17)C18—H18A0.9800
C3—H30.9500C18—H18B0.9800
C4—C51.3943 (17)C18—H18C0.9800
C5—C61.3850 (17)
C4—O1—H1O109.5O3—C10—C11117.60 (11)
C10—O3—H3O109.5O3—C10—C9122.04 (11)
C12—O4—C15117.61 (10)C11—C10—C9120.36 (11)
C7—N1—N2118.01 (10)C10—C11—C12119.89 (11)
C7—N1—H1N121.0C10—C11—H11120.1
N2—N1—H1N121.0C12—C11—H11120.1
C8—N2—N1117.12 (10)O4—C12—C11114.61 (11)
C16—N3—C17120.60 (13)O4—C12—C13124.26 (11)
C16—N3—C18121.12 (14)C11—C12—C13121.13 (11)
C17—N3—C18118.21 (14)C14—C13—C12118.28 (11)
C2—C1—C6118.28 (11)C14—C13—H13120.9
C2—C1—C7117.86 (11)C12—C13—H13120.9
C6—C1—C7123.83 (11)C13—C14—C9122.50 (11)
C3—C2—C1121.20 (11)C13—C14—H14118.7
C3—C2—H2119.4C9—C14—H14118.7
C1—C2—H2119.4O4—C15—H15A109.5
C2—C3—C4120.06 (12)O4—C15—H15B109.5
C2—C3—H3120.0H15A—C15—H15B109.5
C4—C3—H3120.0O4—C15—H15C109.5
O1—C4—C3122.10 (11)H15A—C15—H15C109.5
O1—C4—C5118.30 (11)H15B—C15—H15C109.5
C3—C4—C5119.60 (11)O5—C16—N3125.37 (13)
C6—C5—C4119.98 (11)O5—C16—H16117.3
C6—C5—H5120.0N3—C16—H16117.3
C4—C5—H5120.0N3—C17—H17A109.5
C5—C6—C1120.89 (11)N3—C17—H17B109.5
C5—C6—H6119.6H17A—C17—H17B109.5
C1—C6—H6119.6N3—C17—H17C109.5
O2—C7—N1121.23 (11)H17A—C17—H17C109.5
O2—C7—C1122.05 (11)H17B—C17—H17C109.5
N1—C7—C1116.72 (11)N3—C18—H18A109.5
N2—C8—C9119.62 (11)N3—C18—H18B109.5
N2—C8—H8120.2H18A—C18—H18B109.5
C9—C8—H8120.2N3—C18—H18C109.5
C14—C9—C10117.80 (11)H18A—C18—H18C109.5
C14—C9—C8119.86 (11)H18B—C18—H18C109.5
C10—C9—C8122.34 (11)
C7—N1—N2—C8178.29 (11)N2—C8—C9—C10−4.09 (18)
C6—C1—C2—C3−0.22 (19)C14—C9—C10—O3179.47 (11)
C7—C1—C2—C3177.82 (12)C8—C9—C10—O3−1.25 (19)
C1—C2—C3—C40.4 (2)C14—C9—C10—C11−0.74 (18)
C2—C3—C4—O1178.84 (12)C8—C9—C10—C11178.55 (11)
C2—C3—C4—C5−0.3 (2)O3—C10—C11—C12179.08 (11)
O1—C4—C5—C6−179.11 (11)C9—C10—C11—C12−0.72 (19)
C3—C4—C5—C60.07 (19)C15—O4—C12—C11168.75 (11)
C4—C5—C6—C10.10 (19)C15—O4—C12—C13−11.33 (17)
C2—C1—C6—C5−0.02 (19)C10—C11—C12—O4−178.59 (11)
C7—C1—C6—C5−177.94 (12)C10—C11—C12—C131.49 (19)
N2—N1—C7—O2−5.05 (18)O4—C12—C13—C14179.34 (11)
N2—N1—C7—C1175.38 (10)C11—C12—C13—C14−0.74 (19)
C2—C1—C7—O2−14.53 (18)C12—C13—C14—C9−0.79 (19)
C6—C1—C7—O2163.40 (12)C10—C9—C14—C131.52 (18)
C2—C1—C7—N1165.03 (11)C8—C9—C14—C13−177.79 (12)
C6—C1—C7—N1−17.04 (18)C17—N3—C16—O5−1.2 (2)
N1—N2—C8—C9179.42 (11)C18—N3—C16—O5−178.22 (15)
N2—C8—C9—C14175.18 (12)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1o···O2i0.841.822.656 (1)174
O3—H3o···N20.841.872.607 (1)145
N1—H1n···O50.881.952.787 (1)157

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2837).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Lair, N. M., Ali, H. M. & Ng, S. W. (2009). Acta Cryst. E65, o189. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.

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