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The mol­ecule of the title compound, C15H14N2O4, is roughly planar, except for the methyl H atoms, and displays a trans configuration with respect to the C=N double bond. The dihedral angle between the two rings is 3.7 (2)°. The crystal structure is stabilized by inter­molecular O—H...O and N—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807037014/wn2180sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807037014/wn2180Isup2.hkl
Contains datablock I

CCDC reference: 660184

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.049
  • wR factor = 0.166
  • Data-to-parameter ratio = 16.8

checkCIF/PLATON results

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Alert level C PLAT031_ALERT_4_C Refined Extinction Parameter within Range ...... 3.00 Sigma
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Recently, we have reported a few Schiff base complexes (Qiu, Luo et al., 2006; Qiu, Fang et al., 2006), As an extension of our work on the structural characterization of Schiff base compounds, the crystal structure of the title compound is reported here.

In the title compound, all bond lengths are within normal ranges (Allen et al., 1987) (Fig. 1). The C8N2 bond length of 1.275 (2) Å conforms to the value for a double bond. The bond length of 1.337 (2) Å between N1 and C7 is greater than the value for a double bond, and less than the value for a single bond, because of conjugation in the molecule. The dihedral angle between the two rings is 3.7 (2)°.

The crystal structure is stabilized by intermolecular O—H···O and N—H···O hydrogen bonds. (Table 1 and Fig. 2)

Related literature top

For related literature, see: Allen et al. (1987); Qiu, Fang, Liu & Zhu (2006); Qiu, Luo, Yang & Liu (2006).

Experimental top

The reagents were commercial products and were used without further purification. 3-Hydroxy-4-methoxybenzaldehyde (0.1 mmol, 15.2 mg) and 2-hydroxybenzhydrazide (0.1 mmol, 15.2 mg) were dissolved in ethanol (15 ml). The reaction mixture was stirred for 30 minutes to give a clear solution. After allowing the resulting clear solution to stand at room temperature in air for 9 d, large colourless crystals were formed at the bottom of the vessel on slow evaporation of the solvent. The crystals were isolated, washed three times with ethanol and dried in a vacuum desiccator using anhydrous CaCl2 (yield 66%).

Refinement top

Atom H2, attached to O1, was located in a difference Fourier map and refined with an O—H distance restraint of 1.00 (2) Å. The other H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with C—H, N—H and O—H, distances of 0.93–0.96, 0.86 and 0.82 Å, respectively. and with Uiso(H) = 1.2Ueq(Csp2, N) or 1.5Ueq(methyl C, O).

Structure description top

Recently, we have reported a few Schiff base complexes (Qiu, Luo et al., 2006; Qiu, Fang et al., 2006), As an extension of our work on the structural characterization of Schiff base compounds, the crystal structure of the title compound is reported here.

In the title compound, all bond lengths are within normal ranges (Allen et al., 1987) (Fig. 1). The C8N2 bond length of 1.275 (2) Å conforms to the value for a double bond. The bond length of 1.337 (2) Å between N1 and C7 is greater than the value for a double bond, and less than the value for a single bond, because of conjugation in the molecule. The dihedral angle between the two rings is 3.7 (2)°.

The crystal structure is stabilized by intermolecular O—H···O and N—H···O hydrogen bonds. (Table 1 and Fig. 2)

For related literature, see: Allen et al. (1987); Qiu, Fang, Liu & Zhu (2006); Qiu, Luo, Yang & Liu (2006).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. Dashed lines indicate intramolecular hydrogen bonds.
[Figure 2] Fig. 2. The crystal packing of the title compound, viewed along the a axis. Dashed lines indicate intermolecular hydrogen bonds.
(E)—N'-(3-Hydroxy-4-methoxybenzylidene)-2-hydroxybenzohydrazide top
Crystal data top
C15H14N2O4F(000) = 600
Mr = 286.28Dx = 1.446 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2865 reflections
a = 12.436 (3) Åθ = 4.2–26°
b = 7.1581 (14) ŵ = 0.11 mm1
c = 15.048 (3) ÅT = 298 K
β = 100.95 (3)°Block, colourless
V = 1315.2 (5) Å30.34 × 0.15 × 0.06 mm
Z = 4
Data collection top
Bruker SMART APEX area-detector
diffractometer
3288 independent reflections
Radiation source: fine-focus sealed tube2008 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
ω scansθmax = 28.5°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1616
Tmin = 0.96, Tmax = 0.99k = 99
11560 measured reflectionsl = 1920
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.166 w = 1/[σ2(Fo2) + (0.0815P)2 + 0.0205P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max < 0.001
3288 reflectionsΔρmax = 0.28 e Å3
196 parametersΔρmin = 0.26 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997a), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.009 (3)
Crystal data top
C15H14N2O4V = 1315.2 (5) Å3
Mr = 286.28Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.436 (3) ŵ = 0.11 mm1
b = 7.1581 (14) ÅT = 298 K
c = 15.048 (3) Å0.34 × 0.15 × 0.06 mm
β = 100.95 (3)°
Data collection top
Bruker SMART APEX area-detector
diffractometer
3288 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2008 reflections with I > 2σ(I)
Tmin = 0.96, Tmax = 0.99Rint = 0.030
11560 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.166H atoms treated by a mixture of independent and constrained refinement
S = 1.10Δρmax = 0.28 e Å3
3288 reflectionsΔρmin = 0.26 e Å3
196 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
xyzUiso*/Ueq
C11.19143 (13)0.11923 (19)0.43668 (9)0.0383 (3)
C21.30560 (13)0.1048 (2)0.46186 (11)0.0455 (4)
C31.35507 (15)0.1122 (2)0.55284 (12)0.0585 (5)
H31.43080.10220.56950.070*
C41.29249 (16)0.1342 (2)0.61828 (12)0.0569 (5)
H41.32660.13960.67880.068*
C51.18013 (14)0.1484 (2)0.59570 (10)0.0482 (4)
H51.13840.16310.64040.058*
C61.13091 (13)0.1405 (2)0.50587 (10)0.0426 (4)
H61.05510.14960.49040.051*
C71.13998 (13)0.10751 (19)0.34001 (9)0.0396 (4)
C80.87839 (12)0.1348 (2)0.20923 (9)0.0408 (4)
H80.84000.14610.25630.049*
C90.81933 (12)0.12816 (19)0.11589 (9)0.0384 (3)
C100.87688 (12)0.11754 (19)0.04428 (9)0.0382 (3)
H100.95300.11310.05670.046*
C110.82212 (12)0.11374 (19)0.04359 (9)0.0364 (3)
C120.70753 (13)0.1193 (2)0.06330 (10)0.0423 (4)
C130.64983 (13)0.1286 (2)0.00710 (11)0.0511 (4)
H130.57370.13170.00540.061*
C140.70586 (13)0.1333 (2)0.09602 (11)0.0470 (4)
H140.66680.14000.14290.056*
C210.54812 (16)0.1023 (3)0.17878 (14)0.0823 (7)
H21A0.52310.00630.15120.123*
H21B0.52800.09210.24340.123*
H21C0.51500.21190.15890.123*
H21.3208 (19)0.093 (3)0.3393 (15)0.084 (7)*
N11.03213 (10)0.13674 (18)0.31683 (8)0.0444 (3)
H10.99410.16240.35740.053*
N20.98266 (11)0.12502 (17)0.22650 (8)0.0448 (4)
O11.37067 (10)0.08214 (18)0.39977 (9)0.0628 (4)
O21.19532 (9)0.06595 (17)0.28146 (7)0.0521 (3)
O30.88194 (8)0.10779 (14)0.11127 (7)0.0461 (3)
H110.84030.10590.16050.069*
O40.66287 (9)0.11568 (16)0.15360 (7)0.0558 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0423 (8)0.0413 (8)0.0314 (7)0.0009 (6)0.0073 (6)0.0002 (6)
C20.0432 (9)0.0495 (9)0.0437 (9)0.0010 (7)0.0083 (7)0.0026 (6)
C30.0445 (10)0.0752 (12)0.0513 (10)0.0006 (8)0.0020 (8)0.0011 (8)
C40.0639 (12)0.0638 (11)0.0377 (9)0.0005 (8)0.0035 (8)0.0007 (7)
C50.0609 (10)0.0502 (9)0.0336 (8)0.0018 (7)0.0096 (7)0.0002 (6)
C60.0441 (8)0.0483 (9)0.0357 (8)0.0017 (6)0.0080 (6)0.0003 (6)
C70.0433 (8)0.0446 (8)0.0323 (8)0.0014 (6)0.0107 (6)0.0015 (6)
C80.0440 (9)0.0489 (9)0.0311 (7)0.0006 (6)0.0112 (6)0.0023 (6)
C90.0423 (8)0.0425 (8)0.0315 (7)0.0020 (6)0.0094 (6)0.0020 (6)
C100.0352 (8)0.0453 (8)0.0343 (8)0.0006 (6)0.0072 (6)0.0011 (6)
C110.0375 (8)0.0395 (8)0.0337 (7)0.0003 (6)0.0103 (6)0.0016 (5)
C120.0401 (8)0.0514 (9)0.0337 (8)0.0025 (6)0.0024 (6)0.0034 (6)
C130.0347 (8)0.0733 (11)0.0461 (9)0.0006 (7)0.0100 (7)0.0076 (8)
C140.0410 (8)0.0640 (10)0.0385 (8)0.0023 (7)0.0143 (7)0.0058 (7)
C210.0435 (11)0.143 (2)0.0542 (12)0.0125 (11)0.0075 (9)0.0168 (11)
N10.0432 (7)0.0644 (9)0.0259 (6)0.0056 (6)0.0076 (5)0.0030 (5)
N20.0479 (8)0.0582 (9)0.0281 (7)0.0047 (6)0.0068 (5)0.0014 (5)
O10.0413 (7)0.0958 (10)0.0534 (8)0.0035 (6)0.0142 (6)0.0052 (6)
O20.0480 (7)0.0753 (8)0.0357 (6)0.0072 (5)0.0147 (5)0.0020 (5)
O30.0422 (6)0.0685 (7)0.0285 (5)0.0020 (5)0.0093 (4)0.0001 (4)
O40.0415 (7)0.0885 (9)0.0347 (6)0.0068 (5)0.0001 (5)0.0039 (5)
Geometric parameters (Å, º) top
C1—C21.402 (2)C9—C101.404 (2)
C1—C61.404 (2)C10—C111.3678 (19)
C1—C71.476 (2)C10—H100.9300
C2—O11.357 (2)C11—O31.3712 (16)
C2—C31.391 (2)C11—C121.400 (2)
C3—C41.375 (2)C12—O41.3671 (18)
C3—H30.9300C12—C131.389 (2)
C4—C51.378 (3)C13—C141.387 (2)
C4—H40.9300C13—H130.9300
C5—C61.375 (2)C14—H140.9300
C5—H50.9300C21—O41.409 (2)
C6—H60.9300C21—H21A0.9600
C7—O21.2524 (16)C21—H21B0.9600
C7—N11.337 (2)C21—H21C0.9600
C8—N21.275 (2)N1—N21.3840 (17)
C8—C91.457 (2)N1—H10.8600
C8—H80.9300O1—H21.00 (2)
C9—C141.386 (2)O3—H110.8200
C2—C1—C6117.74 (14)C11—C10—H10119.7
C2—C1—C7119.30 (14)C9—C10—H10119.7
C6—C1—C7122.95 (14)C10—C11—O3118.55 (12)
O1—C2—C3118.17 (15)C10—C11—C12120.27 (13)
O1—C2—C1121.90 (14)O3—C11—C12121.17 (13)
C3—C2—C1119.93 (15)O4—C12—C13125.99 (14)
C4—C3—C2120.29 (16)O4—C12—C11114.52 (13)
C4—C3—H3119.9C13—C12—C11119.49 (14)
C2—C3—H3119.9C14—C13—C12119.95 (15)
C3—C4—C5121.15 (16)C14—C13—H13120.0
C3—C4—H4119.4C12—C13—H13120.0
C5—C4—H4119.4C9—C14—C13120.79 (14)
C6—C5—C4118.73 (15)C9—C14—H14119.6
C6—C5—H5120.6C13—C14—H14119.6
C4—C5—H5120.6O4—C21—H21A109.5
C5—C6—C1122.15 (15)O4—C21—H21B109.5
C5—C6—H6118.9H21A—C21—H21B109.5
C1—C6—H6118.9O4—C21—H21C109.5
O2—C7—N1120.78 (13)H21A—C21—H21C109.5
O2—C7—C1120.90 (14)H21B—C21—H21C109.5
N1—C7—C1118.29 (13)C7—N1—N2118.93 (12)
N2—C8—C9120.12 (13)C7—N1—H1120.5
N2—C8—H8119.9N2—N1—H1120.5
C9—C8—H8119.9C8—N2—N1116.24 (13)
C14—C9—C10118.82 (14)C2—O1—H2105.6 (12)
C14—C9—C8120.88 (14)C11—O3—H11109.5
C10—C9—C8120.30 (14)C12—O4—C21117.93 (14)
C11—C10—C9120.68 (14)
C6—C1—C2—O1179.36 (13)C8—C9—C10—C11179.14 (13)
C7—C1—C2—O10.7 (2)C9—C10—C11—O3178.47 (11)
C6—C1—C2—C30.1 (2)C9—C10—C11—C120.4 (2)
C7—C1—C2—C3178.83 (13)C10—C11—C12—O4179.66 (12)
O1—C2—C3—C4179.71 (15)O3—C11—C12—O40.8 (2)
C1—C2—C3—C40.2 (2)C10—C11—C12—C130.0 (2)
C2—C3—C4—C50.3 (3)O3—C11—C12—C13178.86 (13)
C3—C4—C5—C60.1 (2)O4—C12—C13—C14179.32 (14)
C4—C5—C6—C10.2 (2)C11—C12—C13—C140.3 (2)
C2—C1—C6—C50.4 (2)C10—C9—C14—C130.2 (2)
C7—C1—C6—C5179.01 (13)C8—C9—C14—C13179.45 (13)
C2—C1—C7—O27.4 (2)C12—C13—C14—C90.2 (2)
C6—C1—C7—O2171.25 (13)O2—C7—N1—N21.6 (2)
C2—C1—C7—N1174.64 (12)C1—C7—N1—N2179.59 (11)
C6—C1—C7—N16.7 (2)C9—C8—N2—N1178.54 (12)
N2—C8—C9—C14178.18 (13)C7—N1—N2—C8172.94 (13)
N2—C8—C9—C102.2 (2)C13—C12—O4—C216.4 (2)
C14—C9—C10—C110.5 (2)C11—C12—O4—C21173.87 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3i0.862.262.9616 (16)138
O1—H2···O21.00 (2)1.65 (2)2.5424 (19)146.3 (19)
O3—H11···O2ii0.822.172.8451 (16)140
O3—H11···O40.822.232.6781 (17)115
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+2, y, z.

Experimental details

Crystal data
Chemical formulaC15H14N2O4
Mr286.28
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)12.436 (3), 7.1581 (14), 15.048 (3)
β (°) 100.95 (3)
V3)1315.2 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.34 × 0.15 × 0.06
Data collection
DiffractometerBruker SMART APEX area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.96, 0.99
No. of measured, independent and
observed [I > 2σ(I)] reflections
11560, 3288, 2008
Rint0.030
(sin θ/λ)max1)0.671
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.166, 1.10
No. of reflections3288
No. of parameters196
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.28, 0.26

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3i0.862.262.9616 (16)138.3
O1—H2···O21.00 (2)1.65 (2)2.5424 (19)146.3 (19)
O3—H11···O2ii0.822.172.8451 (16)139.5
O3—H11···O40.822.232.6781 (17)114.7
Symmetry codes: (i) x, y+1/2, z+1/2; (ii) x+2, y, z.
 

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