2-Meth-oxy-N'-(2-methoxy-benzyl-idene)benzohydrazide.

The title Schiff base compound, C(16)H(16)N(2)O(3), was derived from the condensation of 2-methoxy-benzaldehyde with 2-methoxy-benzohydrazide in an ethanol solution. The dihedral angle between the two aromatic rings is 87.5 (3)°. In the crystal structure, the mol-ecules are linked into chains running parallel to the a axis by inter-molecular 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 = 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) Å3

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

Δρmax = 0.15 e Å−3

Δρmin = −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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680802521X/ci2648sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680802521X/ci2648Isup2.hkl

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

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

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 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

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.

	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*

	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)

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

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)

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) .