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The title Schiff base compound, C16H16N2O3, was derived from the condensation of 2-methoxy­benzaldehyde with 2-methoxy­benzohydrazide in an ethanol solution. The dihedral angle between the two aromatic rings is 87.5 (3)°. In the crystal structure, the mol­ecules are linked into chains running parallel to the a axis by inter­molecular N—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680802521X/ci2648sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680802521X/ci2648Isup2.hkl
Contains datablock I

CCDC reference: 702465

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.051
  • wR factor = 0.095
  • Data-to-parameter ratio = 8.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.00 From the CIF: _reflns_number_total 1647 Count of symmetry unique reflns 1660 Completeness (_total/calc) 99.22% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 1 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 2 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

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), we report here the crystal structure of the title new Schiff base compound.

In the title molecule (Fig. 1). the bond lengths have normal values (Allen et al., 1987), and are comparable to those observed in related compounds (Nie, 2008; He, 2008; Shi et al., 2007). The dihedral angle between the two aromatic rings is 87.5 (3)°, indicating that they are almost perpendicular to one another.

In the crystal structure, the molecules are linked into chains (Fig. 2) running parallel to the a axis by intermolecular N–H···O hydrogen bonds (Table 1).

Related literature top

For related literature, see: Lu et al. (2008a,b); 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-methoxybenzaldehyde (0.1 mol) and 2-methoxybenzohydrazide (0.1 mmol) in ethanol (50 ml). The excess ethanol was removed by distillation. The colorless solid obtained was filtered and washed with ethanol. Single crystals suitable for X-ray diffraction were obatined by slow evaporation of an ethanol solution at room temperature.

Refinement top

The imino H atom was located in a difference map and refined with a N–H distance restraint of 0.90 (1) Å. The other H atoms were positioned geometrically (C–H = 0.93-0.96 Å) and refined using a riding model, with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(Cmethyl). In the absence of significant anomalous scattering, Friedel pairs were merged.

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
[Figure 1] Fig. 1. The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. Dashed lines indicate hydrogen bonds.
[Figure 2] Fig. 2. The crystal packing of the title compound, viewed along the b axis. Dashed lines indicate hydrogen bonds.
2-Methoxy-N'-(2-methoxybenzylidene)benzohydrazide top
Crystal data top
C16H16N2O3F(000) = 300
Mr = 284.31Dx = 1.297 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 744 reflections
a = 4.9998 (13) Åθ = 2.5–24.0°
b = 13.475 (4) ŵ = 0.09 mm1
c = 10.824 (3) ÅT = 298 K
β = 93.674 (4)°Block, colourless
V = 727.7 (4) Å30.30 × 0.30 × 0.28 mm
Z = 2
Data collection top
Bruker APEXII CCD area-detector
diffractometer
1647 independent reflections
Radiation source: fine-focus sealed tube1229 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.055
ω scansθmax = 27.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
h = 66
Tmin = 0.973, Tmax = 0.975k = 1716
6081 measured reflectionsl = 1313
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)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095H atoms treated by a mixture of independent and constrained refinement
S = 1.11 w = 1/[σ2(Fo2) + (0.0297P)2]
where P = (Fo2 + 2Fc2)/3
1647 reflections(Δ/σ)max = 0.001
195 parametersΔρmax = 0.16 e Å3
2 restraintsΔρmin = 0.14 e Å3
Crystal data top
C16H16N2O3V = 727.7 (4) Å3
Mr = 284.31Z = 2
Monoclinic, P21Mo Kα radiation
a = 4.9998 (13) ŵ = 0.09 mm1
b = 13.475 (4) ÅT = 298 K
c = 10.824 (3) Å0.30 × 0.30 × 0.28 mm
β = 93.674 (4)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
1647 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
1229 reflections with I > 2σ(I)
Tmin = 0.973, Tmax = 0.975Rint = 0.055
6081 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0502 restraints
wR(F2) = 0.095H atoms treated by a mixture of independent and constrained refinement
S = 1.11Δρmax = 0.16 e Å3
1647 reflectionsΔρmin = 0.14 e Å3
195 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
xyzUiso*/Ueq
O10.4130 (5)0.5063 (2)1.0258 (2)0.0579 (8)
O21.2673 (4)0.71624 (19)0.6930 (2)0.0436 (6)
O30.6361 (5)0.7245 (2)0.4683 (2)0.0513 (6)
N10.8931 (5)0.5916 (2)0.7771 (2)0.0357 (7)
N20.8339 (5)0.67811 (19)0.7116 (3)0.0354 (7)
C10.7337 (7)0.4561 (2)0.8904 (3)0.0371 (9)
C20.5766 (7)0.4321 (3)0.9892 (3)0.0426 (9)
C30.6008 (7)0.3398 (3)1.0439 (3)0.0501 (10)
H30.49530.32331.10860.060*
C40.7794 (8)0.2725 (3)1.0032 (4)0.0549 (11)
H40.79280.21021.04000.066*
C50.9407 (8)0.2954 (3)0.9081 (4)0.0537 (10)
H51.06450.24980.88180.064*
C60.9142 (7)0.3876 (3)0.8529 (3)0.0455 (9)
H61.02160.40360.78870.055*
C70.6996 (7)0.5520 (2)0.8295 (3)0.0377 (8)
H70.53530.58440.82910.045*
C81.0305 (6)0.7328 (2)0.6674 (3)0.0296 (7)
C90.9390 (6)0.8198 (2)0.5913 (3)0.0343 (8)
C100.7391 (6)0.8162 (3)0.4959 (3)0.0358 (8)
C110.6635 (7)0.9012 (3)0.4321 (3)0.0518 (10)
H110.52570.89900.37030.062*
C120.7913 (8)0.9890 (3)0.4597 (4)0.0606 (12)
H120.73841.04620.41680.073*
C130.9946 (8)0.9936 (3)0.5493 (4)0.0617 (12)
H131.08351.05330.56590.074*
C141.0677 (7)0.9096 (3)0.6151 (4)0.0478 (10)
H141.20590.91310.67670.057*
C150.2563 (8)0.4878 (4)1.1267 (4)0.0653 (12)
H15A0.14950.42951.11050.098*
H15B0.14100.54351.13850.098*
H15C0.37140.47781.20010.098*
C160.4372 (8)0.7167 (4)0.3692 (3)0.0712 (12)
H16A0.28210.75420.38850.107*
H16B0.38840.64830.35730.107*
H16C0.50660.74220.29490.107*
H20.662 (3)0.696 (3)0.696 (3)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0577 (16)0.0581 (19)0.0601 (19)0.0064 (15)0.0196 (15)0.0132 (15)
O20.0265 (12)0.0451 (14)0.0586 (14)0.0050 (12)0.0024 (10)0.0062 (13)
O30.0604 (15)0.0471 (15)0.0439 (13)0.0052 (14)0.0149 (11)0.0053 (14)
N10.0391 (16)0.0318 (15)0.0356 (15)0.0028 (13)0.0030 (13)0.0079 (13)
N20.0271 (14)0.0357 (16)0.0428 (16)0.0036 (13)0.0018 (13)0.0124 (13)
C10.037 (2)0.038 (2)0.0354 (19)0.0036 (16)0.0070 (16)0.0053 (16)
C20.041 (2)0.046 (2)0.040 (2)0.0060 (18)0.0050 (18)0.0062 (18)
C30.054 (2)0.051 (3)0.045 (2)0.011 (2)0.0020 (18)0.0176 (19)
C40.069 (3)0.035 (2)0.058 (3)0.000 (2)0.016 (2)0.018 (2)
C50.061 (3)0.043 (2)0.056 (3)0.0023 (19)0.001 (2)0.001 (2)
C60.049 (2)0.042 (2)0.045 (2)0.0021 (19)0.0002 (18)0.0085 (18)
C70.0336 (18)0.043 (2)0.0357 (19)0.0002 (16)0.0008 (16)0.0078 (16)
C80.0279 (17)0.0279 (18)0.0332 (16)0.0013 (15)0.0026 (13)0.0029 (15)
C90.0317 (17)0.0346 (19)0.0377 (18)0.0046 (15)0.0098 (14)0.0017 (16)
C100.0368 (19)0.0353 (19)0.0357 (19)0.0037 (16)0.0051 (15)0.0015 (17)
C110.055 (2)0.056 (3)0.044 (2)0.008 (2)0.001 (2)0.013 (2)
C120.065 (3)0.046 (3)0.071 (3)0.007 (2)0.009 (2)0.027 (2)
C130.072 (3)0.039 (2)0.076 (3)0.010 (2)0.014 (3)0.008 (2)
C140.048 (2)0.037 (2)0.058 (2)0.0087 (19)0.0060 (19)0.003 (2)
C150.060 (3)0.083 (3)0.054 (3)0.002 (3)0.012 (2)0.009 (2)
C160.077 (3)0.078 (3)0.055 (2)0.014 (3)0.023 (2)0.009 (3)
Geometric parameters (Å, º) top
O1—C21.367 (4)C6—H60.93
O1—C151.407 (4)C7—H70.93
O2—C81.220 (3)C8—C91.488 (4)
O3—C101.364 (4)C9—C141.387 (5)
O3—C161.419 (4)C9—C101.391 (4)
N1—C71.270 (4)C10—C111.378 (5)
N1—N21.387 (3)C11—C121.368 (5)
N2—C81.341 (4)C11—H110.93
N2—H20.901 (10)C12—C131.360 (5)
C1—C61.370 (5)C12—H120.93
C1—C21.405 (5)C13—C141.375 (5)
C1—C71.456 (4)C13—H130.93
C2—C31.380 (5)C14—H140.93
C3—C41.365 (5)C15—H15A0.96
C3—H30.93C15—H15B0.96
C4—C51.383 (5)C15—H15C0.96
C4—H40.93C16—H16A0.96
C5—C61.381 (5)C16—H16B0.96
C5—H50.93C16—H16C0.96
C2—O1—C15118.0 (3)C14—C9—C10118.1 (3)
C10—O3—C16118.0 (3)C14—C9—C8117.5 (3)
C7—N1—N2115.9 (3)C10—C9—C8124.3 (3)
C8—N2—N1120.5 (2)O3—C10—C11123.8 (3)
C8—N2—H2120 (3)O3—C10—C9115.9 (3)
N1—N2—H2120 (3)C11—C10—C9120.3 (3)
C6—C1—C2118.8 (3)C12—C11—C10120.0 (4)
C6—C1—C7121.6 (3)C12—C11—H11120.0
C2—C1—C7119.6 (3)C10—C11—H11120.0
O1—C2—C3125.0 (3)C13—C12—C11120.8 (4)
O1—C2—C1115.3 (3)C13—C12—H12119.6
C3—C2—C1119.7 (4)C11—C12—H12119.6
C4—C3—C2120.1 (4)C12—C13—C14119.6 (4)
C4—C3—H3120.0C12—C13—H13120.2
C2—C3—H3119.9C14—C13—H13120.2
C3—C4—C5121.1 (3)C13—C14—C9121.2 (4)
C3—C4—H4119.5C13—C14—H14119.4
C5—C4—H4119.5C9—C14—H14119.4
C6—C5—C4118.6 (4)O1—C15—H15A109.5
C6—C5—H5120.7O1—C15—H15B109.5
C4—C5—H5120.7H15A—C15—H15B109.5
C1—C6—C5121.6 (4)O1—C15—H15C109.5
C1—C6—H6119.2H15A—C15—H15C109.5
C5—C6—H6119.2H15B—C15—H15C109.5
N1—C7—C1120.3 (3)O3—C16—H16A109.5
N1—C7—H7119.9O3—C16—H16B109.5
C1—C7—H7119.9H16A—C16—H16B109.5
O2—C8—N2122.8 (3)O3—C16—H16C109.5
O2—C8—C9122.0 (3)H16A—C16—H16C109.5
N2—C8—C9115.1 (3)H16B—C16—H16C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O2i0.90 (1)1.99 (1)2.873 (3)167 (4)
Symmetry code: (i) x1, y, z.

Experimental details

Crystal data
Chemical formulaC16H16N2O3
Mr284.31
Crystal system, space groupMonoclinic, P21
Temperature (K)298
a, b, c (Å)4.9998 (13), 13.475 (4), 10.824 (3)
β (°) 93.674 (4)
V3)727.7 (4)
Z2
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.30 × 0.30 × 0.28
Data collection
DiffractometerBruker APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2004)
Tmin, Tmax0.973, 0.975
No. of measured, independent and
observed [I > 2σ(I)] reflections
6081, 1647, 1229
Rint0.055
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.095, 1.11
No. of reflections1647
No. of parameters195
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.16, 0.14

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···AD—HH···AD···AD—H···A
N2—H2···O2i0.90 (1)1.99 (1)2.873 (3)167 (4)
Symmetry code: (i) x1, y, z.
 

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