2-Meth­oxy-N′-(2-methoxy­benzyl­idene)benzohydrazide

Abstract

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.

Related literature

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

Crystal data

• C₁₆H₁₆N₂O₃

• M _r = 284.31

• Monoclinic,

• a = 4.9998 (13) Å

• b = 13.475 (4) Å

• c = 10.824 (3) Å

• β = 93.674 (4)°

• V = 727.7 (4) ų

• Z = 2

• Mo Kα radiation

• μ = 0.09 mm⁻¹

• T = 298 (2) K

• 0.30 × 0.30 × 0.28 mm

Data collection

• Bruker APEXII CCD area-detector diffractometer

• Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.973, T _max = 0.975

• 6081 measured reflections

• 1647 independent reflections

• 1229 reflections with I > 2σ(I)

• R _int = 0.055

Refinement

• R[F ² > 2σ(F ²)] = 0.050

• wR(F ²) = 0.095

• S = 1.11

• 1647 reflections

• 195 parameters

• 2 restraints

• H atoms treated by a mixture of independent and constrained refinement

• Δρ_max = 0.15 e Å⁻³

• Δρ_min = −0.14 e Å⁻³

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.

Supplementary Material

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2i	0.90 (1)	1.99 (1)	2.873 (3)	167 (4)

Symmetry code: (i) .

supplementary crystallographic information

Comment

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).

Experimental

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

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 U_iso(H) = 1.2U_eq(C) and 1.5U_eq(C_methyl). In the absence of significant anomalous scattering, Friedel pairs were merged.

Figures

Fig. 1.

The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. Dashed lines indicate hydrogen bonds.

Fig. 2.

The crystal packing of the title compound, viewed along the b axis. Dashed lines indicate hydrogen bonds.

Crystal data

C16H16N2O3	F000 = 300
Mr = 284.31	Dx = 1.297 Mg m−3
Monoclinic, P21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 744 reflections
a = 4.9998 (13) Å	θ = 2.5–24.0º
b = 13.475 (4) Å	µ = 0.09 mm−1
c = 10.824 (3) Å	T = 298 (2) K
β = 93.674 (4)º	Block, colourless
V = 727.7 (4) Å3	0.30 × 0.30 × 0.28 mm
Z = 2

Data collection

Bruker APEXII CCD area-detector diffractometer	1647 independent reflections
Radiation source: fine-focus sealed tube	1229 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.055
T = 298(2) K	θmax = 27.0º
ω scans	θmin = 1.9º
Absorption correction: multi-scan(SADABS; Sheldrick, 2004)	h = −6→6
Tmin = 0.973, Tmax = 0.975	k = −17→16
6081 measured reflections	l = −13→13

Refinement

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.095	w = 1/[σ2(Fo2) + (0.0297P)2] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max = 0.001
1647 reflections	Δρmax = 0.16 e Å−3
195 parameters	Δρmin = −0.14 e Å−3
2 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.4130 (5)	0.5063 (2)	1.0258 (2)	0.0579 (8)
O2	1.2673 (4)	0.71624 (19)	0.6930 (2)	0.0436 (6)
O3	0.6361 (5)	0.7245 (2)	0.4683 (2)	0.0513 (6)
N1	0.8931 (5)	0.5916 (2)	0.7771 (2)	0.0357 (7)
N2	0.8339 (5)	0.67811 (19)	0.7116 (3)	0.0354 (7)
C1	0.7337 (7)	0.4561 (2)	0.8904 (3)	0.0371 (9)
C2	0.5766 (7)	0.4321 (3)	0.9892 (3)	0.0426 (9)
C3	0.6008 (7)	0.3398 (3)	1.0439 (3)	0.0501 (10)
H3	0.4953	0.3233	1.1086	0.060*
C4	0.7794 (8)	0.2725 (3)	1.0032 (4)	0.0549 (11)
H4	0.7928	0.2102	1.0400	0.066*
C5	0.9407 (8)	0.2954 (3)	0.9081 (4)	0.0537 (10)
H5	1.0645	0.2498	0.8818	0.064*
C6	0.9142 (7)	0.3876 (3)	0.8529 (3)	0.0455 (9)
H6	1.0216	0.4036	0.7887	0.055*
C7	0.6996 (7)	0.5520 (2)	0.8295 (3)	0.0377 (8)
H7	0.5353	0.5844	0.8291	0.045*
C8	1.0305 (6)	0.7328 (2)	0.6674 (3)	0.0296 (7)
C9	0.9390 (6)	0.8198 (2)	0.5913 (3)	0.0343 (8)
C10	0.7391 (6)	0.8162 (3)	0.4959 (3)	0.0358 (8)
C11	0.6635 (7)	0.9012 (3)	0.4321 (3)	0.0518 (10)
H11	0.5257	0.8990	0.3703	0.062*
C12	0.7913 (8)	0.9890 (3)	0.4597 (4)	0.0606 (12)
H12	0.7384	1.0462	0.4168	0.073*
C13	0.9946 (8)	0.9936 (3)	0.5493 (4)	0.0617 (12)
H13	1.0835	1.0533	0.5659	0.074*
C14	1.0677 (7)	0.9096 (3)	0.6151 (4)	0.0478 (10)
H14	1.2059	0.9131	0.6767	0.057*
C15	0.2563 (8)	0.4878 (4)	1.1267 (4)	0.0653 (12)
H15A	0.1495	0.4295	1.1105	0.098*
H15B	0.1410	0.5435	1.1385	0.098*
H15C	0.3714	0.4778	1.2001	0.098*
C16	0.4372 (8)	0.7167 (4)	0.3692 (3)	0.0712 (12)
H16A	0.2821	0.7542	0.3885	0.107*
H16B	0.3884	0.6483	0.3573	0.107*
H16C	0.5066	0.7422	0.2949	0.107*
H2	0.662 (3)	0.696 (3)	0.696 (3)	0.080*

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
O1	0.0577 (16)	0.0581 (19)	0.0601 (19)	0.0064 (15)	0.0196 (15)	0.0132 (15)
O2	0.0265 (12)	0.0451 (14)	0.0586 (14)	0.0050 (12)	−0.0024 (10)	0.0062 (13)
O3	0.0604 (15)	0.0471 (15)	0.0439 (13)	−0.0052 (14)	−0.0149 (11)	0.0053 (14)
N1	0.0391 (16)	0.0318 (15)	0.0356 (15)	0.0028 (13)	−0.0030 (13)	0.0079 (13)
N2	0.0271 (14)	0.0357 (16)	0.0428 (16)	0.0036 (13)	−0.0018 (13)	0.0124 (13)
C1	0.037 (2)	0.038 (2)	0.0354 (19)	−0.0036 (16)	−0.0070 (16)	0.0053 (16)
C2	0.041 (2)	0.046 (2)	0.040 (2)	−0.0060 (18)	−0.0050 (18)	0.0062 (18)
C3	0.054 (2)	0.051 (3)	0.045 (2)	−0.011 (2)	−0.0020 (18)	0.0176 (19)
C4	0.069 (3)	0.035 (2)	0.058 (3)	0.000 (2)	−0.016 (2)	0.018 (2)
C5	0.061 (3)	0.043 (2)	0.056 (3)	0.0023 (19)	−0.001 (2)	0.001 (2)
C6	0.049 (2)	0.042 (2)	0.045 (2)	−0.0021 (19)	0.0002 (18)	0.0085 (18)
C7	0.0336 (18)	0.043 (2)	0.0357 (19)	0.0002 (16)	−0.0008 (16)	0.0078 (16)
C8	0.0279 (17)	0.0279 (18)	0.0332 (16)	−0.0013 (15)	0.0026 (13)	−0.0029 (15)
C9	0.0317 (17)	0.0346 (19)	0.0377 (18)	0.0046 (15)	0.0098 (14)	0.0017 (16)
C10	0.0368 (19)	0.0353 (19)	0.0357 (19)	0.0037 (16)	0.0051 (15)	0.0015 (17)
C11	0.055 (2)	0.056 (3)	0.044 (2)	0.008 (2)	0.001 (2)	0.013 (2)
C12	0.065 (3)	0.046 (3)	0.071 (3)	0.007 (2)	0.009 (2)	0.027 (2)
C13	0.072 (3)	0.039 (2)	0.076 (3)	−0.010 (2)	0.014 (3)	0.008 (2)
C14	0.048 (2)	0.037 (2)	0.058 (2)	−0.0087 (19)	0.0060 (19)	0.003 (2)
C15	0.060 (3)	0.083 (3)	0.054 (3)	−0.002 (3)	0.012 (2)	0.009 (2)
C16	0.077 (3)	0.078 (3)	0.055 (2)	−0.014 (3)	−0.023 (2)	0.009 (3)

Geometric parameters (Å, °)

O1—C2	1.367 (4)	C6—H6	0.93
O1—C15	1.407 (4)	C7—H7	0.93
O2—C8	1.220 (3)	C8—C9	1.488 (4)
O3—C10	1.364 (4)	C9—C14	1.387 (5)
O3—C16	1.419 (4)	C9—C10	1.391 (4)
N1—C7	1.270 (4)	C10—C11	1.378 (5)
N1—N2	1.387 (3)	C11—C12	1.368 (5)
N2—C8	1.341 (4)	C11—H11	0.93
N2—H2	0.901 (10)	C12—C13	1.360 (5)
C1—C6	1.370 (5)	C12—H12	0.93
C1—C2	1.405 (5)	C13—C14	1.375 (5)
C1—C7	1.456 (4)	C13—H13	0.93
C2—C3	1.380 (5)	C14—H14	0.93
C3—C4	1.365 (5)	C15—H15A	0.96
C3—H3	0.93	C15—H15B	0.96
C4—C5	1.383 (5)	C15—H15C	0.96
C4—H4	0.93	C16—H16A	0.96
C5—C6	1.381 (5)	C16—H16B	0.96
C5—H5	0.93	C16—H16C	0.96
C2—O1—C15	118.0 (3)	C14—C9—C10	118.1 (3)
C10—O3—C16	118.0 (3)	C14—C9—C8	117.5 (3)
C7—N1—N2	115.9 (3)	C10—C9—C8	124.3 (3)
C8—N2—N1	120.5 (2)	O3—C10—C11	123.8 (3)
C8—N2—H2	120 (3)	O3—C10—C9	115.9 (3)
N1—N2—H2	120 (3)	C11—C10—C9	120.3 (3)
C6—C1—C2	118.8 (3)	C12—C11—C10	120.0 (4)
C6—C1—C7	121.6 (3)	C12—C11—H11	120.0
C2—C1—C7	119.6 (3)	C10—C11—H11	120.0
O1—C2—C3	125.0 (3)	C13—C12—C11	120.8 (4)
O1—C2—C1	115.3 (3)	C13—C12—H12	119.6
C3—C2—C1	119.7 (4)	C11—C12—H12	119.6
C4—C3—C2	120.1 (4)	C12—C13—C14	119.6 (4)
C4—C3—H3	120.0	C12—C13—H13	120.2
C2—C3—H3	119.9	C14—C13—H13	120.2
C3—C4—C5	121.1 (3)	C13—C14—C9	121.2 (4)
C3—C4—H4	119.5	C13—C14—H14	119.4
C5—C4—H4	119.5	C9—C14—H14	119.4
C6—C5—C4	118.6 (4)	O1—C15—H15A	109.5
C6—C5—H5	120.7	O1—C15—H15B	109.5
C4—C5—H5	120.7	H15A—C15—H15B	109.5
C1—C6—C5	121.6 (4)	O1—C15—H15C	109.5
C1—C6—H6	119.2	H15A—C15—H15C	109.5
C5—C6—H6	119.2	H15B—C15—H15C	109.5
N1—C7—C1	120.3 (3)	O3—C16—H16A	109.5
N1—C7—H7	119.9	O3—C16—H16B	109.5
C1—C7—H7	119.9	H16A—C16—H16B	109.5
O2—C8—N2	122.8 (3)	O3—C16—H16C	109.5
O2—C8—C9	122.0 (3)	H16A—C16—H16C	109.5
N2—C8—C9	115.1 (3)	H16B—C16—H16C	109.5

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2i	0.90 (1)	1.99 (1)	2.873 (3)	167 (4)

Symmetry codes: (i) x−1, y, z.