(E)-2-Meth-oxy-N'-(4-methoxy-benzyl-idene)benzohydrazide.

The mol-ecule of the title compound, C(16)H(16)N(2)O(3), displays an E configuration about the C=N bond. The dihedral angle between the two benzene rings is 99.0 (2)°. In the crystal structure, mol-ecules are linked through inter-molecular N-H⋯O hydrogen bonds, forming chains running along the b axis.

Related literature

For examples of the crystal structures of hydrazone compounds, see: Mohd Lair et al. (2009 ▶); Fun et al. (2008 ▶); Li & Ban (2009 ▶); Zhu et al. (2009 ▶); Yang (2007 ▶); You et al. (2008 ▶). For the hydrazone compounds we have reported previously, see: Qu et al. (2008 ▶); Yang et al. (2008 ▶); Cao & Lu (2009a ▶,b ▶); Qu & Cao (2009 ▶); Cao & Wang (2009 ▶).

Experimental

Crystal data

C16H16N2O3

M = 284.31

Orthorhombic,

a = 14.990 (1) Å

b = 8.076 (1) Å

c = 24.122 (2) Å

V = 2920.2 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.17 × 0.15 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.985, T max = 0.987

16039 measured reflections

3011 independent reflections

1225 reflections with I > 2σ(I)

R int = 0.117

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.149

S = 0.92

3011 reflections

196 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809039713/rz2367sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039713/rz2367Isup2.hkl

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

C16H16N2O3	F(000) = 1200
Mr = 284.31	Dx = 1.293 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 687 reflections
a = 14.990 (1) Å	θ = 2.6–24.5°
b = 8.076 (1) Å	µ = 0.09 mm−1
c = 24.122 (2) Å	T = 298 K
V = 2920.2 (5) Å3	Block, colourless
Z = 8	0.17 × 0.15 × 0.15 mm

Bruker SMART CCD area-detector diffractometer	3011 independent reflections
Radiation source: fine-focus sealed tube	1225 reflections with I > 2σ(I)
graphite	Rint = 0.117
ω scans	θmax = 26.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −18→14
Tmin = 0.985, Tmax = 0.987	k = −10→9
16039 measured reflections	l = −29→30

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) = 0.149	w = 1/[σ2(Fo2) + (0.0609P)2] where P = (Fo2 + 2Fc2)/3
S = 0.92	(Δ/σ)max = 0.001
3011 reflections	Δρmax = 0.17 e Å−3
196 parameters	Δρmin = −0.15 e Å−3
1 restraint	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0064 (9)

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
N1	0.24763 (16)	0.2770 (3)	0.63202 (9)	0.0545 (7)
N2	0.22280 (16)	0.3524 (3)	0.68158 (10)	0.0538 (7)
O1	0.44582 (16)	0.0703 (3)	0.41056 (8)	0.0775 (7)
O2	0.15343 (14)	0.1210 (3)	0.71066 (8)	0.0674 (6)
O3	0.12187 (13)	0.6010 (3)	0.73232 (9)	0.0704 (7)
C1	0.3439 (2)	0.2823 (3)	0.55389 (11)	0.0513 (8)
C2	0.2946 (2)	0.1755 (4)	0.52098 (12)	0.0596 (9)
H2	0.2364	0.1493	0.5310	0.072*
C3	0.3305 (2)	0.1079 (4)	0.47389 (13)	0.0629 (9)
H3	0.2962	0.0374	0.4521	0.076*
C4	0.4177 (2)	0.1438 (4)	0.45845 (12)	0.0591 (9)
C5	0.4675 (2)	0.2488 (4)	0.49037 (12)	0.0638 (9)
H5	0.5260	0.2732	0.4806	0.077*
C6	0.4299 (2)	0.3188 (4)	0.53754 (12)	0.0628 (9)
H6	0.4637	0.3921	0.5586	0.075*
C7	0.5366 (2)	0.0952 (5)	0.39380 (14)	0.0938 (12)
H7A	0.5468	0.2109	0.3873	0.141*
H7B	0.5480	0.0342	0.3604	0.141*
H7C	0.5759	0.0571	0.4225	0.141*
C8	0.3105 (2)	0.3490 (4)	0.60596 (12)	0.0565 (8)
H8	0.3353	0.4453	0.6204	0.068*
C9	0.17680 (19)	0.2648 (4)	0.71898 (12)	0.0518 (8)
C10	0.15877 (18)	0.3466 (3)	0.77329 (11)	0.0473 (7)
C11	0.13233 (17)	0.5107 (4)	0.77954 (13)	0.0518 (8)
C12	0.11833 (19)	0.5735 (4)	0.83241 (14)	0.0632 (9)
H12	0.1021	0.6838	0.8370	0.076*
C13	0.1284 (2)	0.4732 (5)	0.87795 (14)	0.0754 (10)
H13	0.1197	0.5170	0.9132	0.091*
C14	0.1508 (2)	0.3111 (5)	0.87232 (14)	0.0771 (10)
H14	0.1560	0.2432	0.9033	0.092*
C15	0.1658 (2)	0.2486 (4)	0.81986 (13)	0.0636 (9)
H15	0.1811	0.1376	0.8159	0.076*
C16	0.0725 (2)	0.7525 (4)	0.73634 (14)	0.0903 (12)
H16A	0.0178	0.7328	0.7559	0.135*
H16B	0.0595	0.7929	0.6998	0.135*
H16C	0.1073	0.8332	0.7560	0.135*
H2A	0.2470 (19)	0.452 (2)	0.6882 (13)	0.080*

	U11	U22	U33	U12	U13	U23
N1	0.0619 (17)	0.0495 (16)	0.0521 (15)	0.0013 (13)	0.0033 (13)	−0.0108 (13)
N2	0.0596 (17)	0.0448 (16)	0.0572 (15)	−0.0048 (13)	0.0059 (13)	−0.0116 (14)
O1	0.0876 (18)	0.0791 (17)	0.0657 (14)	0.0123 (13)	0.0205 (13)	−0.0048 (12)
O2	0.0754 (15)	0.0436 (14)	0.0831 (15)	−0.0082 (11)	0.0145 (12)	−0.0180 (12)
O3	0.0831 (16)	0.0475 (13)	0.0806 (15)	0.0149 (11)	0.0209 (13)	0.0047 (12)
C1	0.058 (2)	0.0453 (18)	0.0505 (17)	0.0018 (15)	−0.0028 (15)	0.0002 (15)
C2	0.055 (2)	0.064 (2)	0.0597 (19)	−0.0010 (16)	0.0036 (16)	−0.0066 (17)
C3	0.064 (2)	0.066 (2)	0.0587 (19)	−0.0018 (17)	−0.0036 (17)	−0.0125 (17)
C4	0.071 (2)	0.052 (2)	0.0545 (19)	0.0117 (17)	0.0061 (17)	0.0034 (16)
C5	0.062 (2)	0.063 (2)	0.067 (2)	−0.0049 (17)	0.0077 (18)	0.0079 (18)
C6	0.068 (2)	0.060 (2)	0.060 (2)	−0.0112 (17)	−0.0024 (17)	−0.0026 (17)
C7	0.089 (3)	0.108 (3)	0.085 (2)	0.030 (2)	0.036 (2)	0.014 (2)
C8	0.067 (2)	0.0452 (19)	0.0571 (19)	−0.0020 (16)	−0.0020 (17)	−0.0046 (16)
C9	0.0468 (18)	0.0441 (19)	0.065 (2)	0.0042 (15)	0.0003 (15)	−0.0089 (17)
C10	0.0449 (17)	0.0409 (18)	0.0560 (18)	0.0016 (13)	0.0002 (14)	−0.0063 (15)
C11	0.0481 (19)	0.0448 (19)	0.062 (2)	−0.0015 (14)	0.0059 (15)	−0.0028 (16)
C12	0.058 (2)	0.054 (2)	0.078 (2)	0.0001 (15)	0.0160 (18)	−0.0192 (19)
C13	0.082 (3)	0.080 (3)	0.064 (2)	−0.004 (2)	0.0088 (19)	−0.018 (2)
C14	0.092 (3)	0.077 (3)	0.062 (2)	0.013 (2)	0.0017 (19)	0.002 (2)
C15	0.071 (2)	0.053 (2)	0.067 (2)	0.0123 (17)	0.0026 (17)	−0.0045 (18)
C16	0.089 (3)	0.057 (2)	0.124 (3)	0.031 (2)	0.033 (2)	0.016 (2)

N1—C8	1.273 (3)	C6—H6	0.9300
N1—N2	1.392 (3)	C7—H7A	0.9600
N2—C9	1.338 (3)	C7—H7B	0.9600
N2—H2A	0.899 (10)	C7—H7C	0.9600
O1—C4	1.366 (3)	C8—H8	0.9300
O1—C7	1.434 (4)	C9—C10	1.492 (4)
O2—C9	1.230 (3)	C10—C15	1.378 (4)
O3—C11	1.362 (3)	C10—C11	1.391 (4)
O3—C16	1.432 (3)	C11—C12	1.388 (4)
C1—C6	1.381 (4)	C12—C13	1.373 (4)
C1—C2	1.386 (4)	C12—H12	0.9300
C1—C8	1.455 (4)	C13—C14	1.359 (5)
C2—C3	1.370 (4)	C13—H13	0.9300
C2—H2	0.9300	C14—C15	1.381 (4)
C3—C4	1.390 (4)	C14—H14	0.9300
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.367 (4)	C16—H16A	0.9600
C5—C6	1.390 (4)	C16—H16B	0.9600
C5—H5	0.9300	C16—H16C	0.9600
C8—N1—N2	115.0 (2)	N1—C8—C1	120.8 (3)
C9—N2—N1	119.1 (2)	N1—C8—H8	119.6
C9—N2—H2A	124 (2)	C1—C8—H8	119.6
N1—N2—H2A	116 (2)	O2—C9—N2	122.4 (3)
C4—O1—C7	118.1 (3)	O2—C9—C10	120.7 (3)
C11—O3—C16	117.4 (2)	N2—C9—C10	116.9 (3)
C6—C1—C2	117.8 (3)	C15—C10—C11	118.7 (3)
C6—C1—C8	119.3 (3)	C15—C10—C9	116.6 (3)
C2—C1—C8	122.8 (3)	C11—C10—C9	124.6 (3)
C3—C2—C1	120.9 (3)	O3—C11—C12	123.7 (3)
C3—C2—H2	119.5	O3—C11—C10	116.9 (3)
C1—C2—H2	119.5	C12—C11—C10	119.4 (3)
C2—C3—C4	120.5 (3)	C13—C12—C11	120.2 (3)
C2—C3—H3	119.7	C13—C12—H12	119.9
C4—C3—H3	119.7	C11—C12—H12	119.9
O1—C4—C5	125.3 (3)	C14—C13—C12	121.0 (3)
O1—C4—C3	115.3 (3)	C14—C13—H13	119.5
C5—C4—C3	119.5 (3)	C12—C13—H13	119.5
C4—C5—C6	119.5 (3)	C13—C14—C15	119.0 (3)
C4—C5—H5	120.2	C13—C14—H14	120.5
C6—C5—H5	120.2	C15—C14—H14	120.5
C1—C6—C5	121.7 (3)	C10—C15—C14	121.6 (3)
C1—C6—H6	119.2	C10—C15—H15	119.2
C5—C6—H6	119.2	C14—C15—H15	119.2
O1—C7—H7A	109.5	O3—C16—H16A	109.5
O1—C7—H7B	109.5	O3—C16—H16B	109.5
H7A—C7—H7B	109.5	H16A—C16—H16B	109.5
O1—C7—H7C	109.5	O3—C16—H16C	109.5
H7A—C7—H7C	109.5	H16A—C16—H16C	109.5
H7B—C7—H7C	109.5	H16B—C16—H16C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2i	0.90 (1)	2.09 (2)	2.940 (3)	157 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2i	0.899 (10)	2.093 (15)	2.940 (3)	157 (3)

Symmetry code: (i) .