(E)-N'-[1-(2-Hydroxy-phen-yl)ethyl-idene]-3-methoxy-benzohydrazide.

In the title compound, C(16)H(16)N(2)O(3), the benzohydrazide group is not planar and the mol-ecule exists in a trans configuration with respect to the methyl-idene unit. The dihedral angle between the two substituted benzene rings is 26.9 (2)°. In the crystal structure, the mol-ecular packing is stabilized by intra-molecular O-H⋯N and inter-molecular N-H⋯O hydrogen bonds. The inter-molecular hydrogen bonding forms chains parallel to the b axis.

Related literature

For the biological activities of hydrazones, see: Zhong et al. (2007 ▶); Raj et al. (2007 ▶); Jimenez-Pulido et al. (2008 ▶). For related structures, see: Ban & Li (2008a ▶,b ▶); Yehye et al. (2008 ▶); Fun et al. (2008a ▶,b ▶); Yang et al. (2008 ▶); Ejsmont et al. (2008 ▶).

Experimental

Crystal data

C16H16N2O3

M = 284.31

Orthorhombic,

a = 12.932 (2) Å

b = 8.756 (2) Å

c = 25.784 (3) Å

V = 2919.7 (9) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.27 × 0.23 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.976, T max = 0.982

22735 measured reflections

3180 independent reflections

2023 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.145

S = 1.01

3180 reflections

196 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.13 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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/S1600536809010228/bx2198sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010228/bx2198Isup2.hkl

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

C16H16N2O3	F(000) = 1200
Mr = 284.31	Dx = 1.294 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2030 reflections
a = 12.932 (2) Å	θ = 2.3–24.6°
b = 8.756 (2) Å	µ = 0.09 mm−1
c = 25.784 (3) Å	T = 298 K
V = 2919.7 (9) Å3	Block, colourless
Z = 8	0.27 × 0.23 × 0.20 mm

Bruker SMART CCD area-detector diffractometer	3180 independent reflections
Radiation source: fine-focus sealed tube	2023 reflections with I > 2σ(I)
graphite	Rint = 0.060
ω scans	θmax = 27.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→16
Tmin = 0.976, Tmax = 0.982	k = −11→11
22735 measured reflections	l = −32→32

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0537P)2 + 0.9645P] where P = (Fo2 + 2Fc2)/3
3180 reflections	(Δ/σ)max < 0.001
196 parameters	Δρmax = 0.17 e Å−3
1 restraint	Δρmin = −0.13 e Å−3

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	0.36951 (13)	−0.23812 (18)	0.55231 (7)	0.0649 (5)
H1	0.3402	−0.1716	0.5692	0.097*
O2	0.16810 (12)	−0.08166 (16)	0.63341 (7)	0.0637 (5)
O3	−0.13883 (13)	0.2606 (3)	0.68697 (8)	0.0904 (7)
N1	0.35910 (13)	−0.00001 (18)	0.60790 (6)	0.0449 (4)
N2	0.29750 (13)	0.09206 (19)	0.63821 (7)	0.0455 (4)
C1	0.51395 (16)	−0.0694 (2)	0.56716 (8)	0.0464 (5)
C2	0.46801 (19)	−0.1972 (2)	0.54406 (8)	0.0531 (6)
C3	0.5262 (2)	−0.2881 (3)	0.51064 (10)	0.0698 (7)
H3	0.4956	−0.3729	0.4953	0.084*
C4	0.6267 (3)	−0.2557 (3)	0.49994 (11)	0.0783 (9)
H4	0.6643	−0.3189	0.4779	0.094*
C5	0.6727 (2)	−0.1300 (3)	0.52166 (10)	0.0726 (8)
H5	0.7413	−0.1067	0.5141	0.087*
C6	0.61702 (17)	−0.0388 (3)	0.55467 (9)	0.0605 (6)
H6	0.6489	0.0462	0.5692	0.073*
C7	0.45502 (16)	0.0315 (2)	0.60247 (8)	0.0460 (5)
C8	0.50836 (18)	0.1605 (3)	0.62968 (11)	0.0736 (8)
H8A	0.5115	0.2475	0.6071	0.110*
H8B	0.5772	0.1299	0.6389	0.110*
H8C	0.4706	0.1867	0.6605	0.110*
C9	0.20029 (16)	0.0434 (2)	0.64786 (8)	0.0453 (5)
C10	0.13506 (15)	0.1510 (2)	0.67804 (7)	0.0416 (5)
C11	0.02940 (15)	0.1511 (2)	0.66810 (8)	0.0472 (5)
H11	0.0020	0.0846	0.6436	0.057*
C12	−0.03443 (18)	0.2490 (3)	0.69451 (9)	0.0587 (6)
C13	0.0058 (2)	0.3454 (3)	0.73150 (10)	0.0744 (8)
H13	−0.0375	0.4117	0.7494	0.089*
C14	0.1094 (2)	0.3437 (3)	0.74187 (10)	0.0741 (8)
H14	0.1361	0.4087	0.7671	0.089*
C15	0.17528 (17)	0.2464 (3)	0.71537 (9)	0.0551 (6)
H15	0.2457	0.2454	0.7227	0.066*
C16	−0.1850 (2)	0.1657 (4)	0.64939 (12)	0.0932 (10)
H16A	−0.1543	0.1853	0.6162	0.140*
H16B	−0.2578	0.1865	0.6478	0.140*
H16C	−0.1743	0.0607	0.6586	0.140*
H2	0.3118 (19)	0.1919 (13)	0.6414 (10)	0.080*

	U11	U22	U33	U12	U13	U23
O1	0.0719 (12)	0.0497 (10)	0.0731 (12)	−0.0087 (9)	−0.0043 (9)	−0.0107 (8)
O2	0.0519 (9)	0.0352 (8)	0.1039 (13)	−0.0034 (7)	−0.0095 (9)	−0.0069 (8)
O3	0.0454 (10)	0.1393 (19)	0.0865 (14)	0.0128 (11)	0.0099 (10)	−0.0058 (13)
N1	0.0432 (10)	0.0389 (9)	0.0524 (10)	0.0035 (8)	−0.0032 (8)	−0.0017 (8)
N2	0.0426 (10)	0.0339 (9)	0.0602 (11)	0.0017 (8)	0.0002 (8)	−0.0049 (9)
C1	0.0512 (13)	0.0411 (12)	0.0468 (12)	0.0051 (10)	−0.0031 (10)	0.0027 (9)
C2	0.0687 (16)	0.0415 (13)	0.0490 (13)	0.0059 (11)	−0.0025 (11)	0.0042 (10)
C3	0.104 (2)	0.0451 (15)	0.0607 (16)	0.0093 (14)	0.0061 (15)	−0.0058 (12)
C4	0.101 (2)	0.0675 (18)	0.0664 (17)	0.0287 (17)	0.0235 (16)	0.0042 (14)
C5	0.0695 (17)	0.0764 (19)	0.0720 (17)	0.0163 (15)	0.0202 (14)	0.0064 (15)
C6	0.0561 (15)	0.0587 (15)	0.0666 (15)	0.0054 (12)	0.0031 (12)	0.0024 (12)
C7	0.0440 (12)	0.0407 (11)	0.0534 (13)	0.0070 (9)	−0.0078 (10)	−0.0012 (10)
C8	0.0466 (14)	0.0697 (17)	0.105 (2)	0.0040 (12)	−0.0096 (14)	−0.0346 (16)
C9	0.0429 (12)	0.0363 (11)	0.0567 (13)	0.0008 (9)	−0.0096 (10)	0.0052 (10)
C10	0.0436 (11)	0.0387 (11)	0.0427 (11)	−0.0043 (9)	−0.0015 (9)	0.0073 (9)
C11	0.0445 (12)	0.0505 (13)	0.0466 (12)	−0.0060 (10)	0.0016 (10)	0.0068 (10)
C12	0.0467 (14)	0.0763 (17)	0.0531 (14)	0.0014 (12)	0.0097 (11)	0.0084 (13)
C13	0.0687 (18)	0.094 (2)	0.0608 (16)	0.0095 (15)	0.0184 (14)	−0.0177 (15)
C14	0.0771 (19)	0.092 (2)	0.0529 (15)	−0.0094 (16)	0.0051 (13)	−0.0249 (14)
C15	0.0464 (12)	0.0690 (15)	0.0498 (13)	−0.0057 (11)	−0.0005 (10)	−0.0029 (12)
C16	0.0430 (15)	0.140 (3)	0.097 (2)	−0.0071 (16)	−0.0068 (15)	0.012 (2)

O1—C2	1.340 (3)	C6—H6	0.9300
O1—H1	0.8200	C7—C8	1.498 (3)
O2—C9	1.229 (2)	C8—H8A	0.9600
O3—C12	1.368 (3)	C8—H8B	0.9600
O3—C16	1.409 (4)	C8—H8C	0.9600
N1—C7	1.278 (2)	C9—C10	1.485 (3)
N1—N2	1.377 (2)	C10—C15	1.376 (3)
N2—C9	1.351 (3)	C10—C11	1.390 (3)
N2—H2	0.897 (10)	C11—C12	1.371 (3)
C1—C6	1.397 (3)	C11—H11	0.9300
C1—C2	1.401 (3)	C12—C13	1.376 (3)
C1—C7	1.480 (3)	C13—C14	1.367 (4)
C2—C3	1.394 (3)	C13—H13	0.9300
C3—C4	1.358 (4)	C14—C15	1.385 (3)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.371 (4)	C15—H15	0.9300
C4—H4	0.9300	C16—H16A	0.9600
C5—C6	1.372 (3)	C16—H16B	0.9600
C5—H5	0.9300	C16—H16C	0.9600
C2—O1—H1	109.5	C7—C8—H8C	109.5
C12—O3—C16	118.2 (2)	H8A—C8—H8C	109.5
C7—N1—N2	119.81 (17)	H8B—C8—H8C	109.5
C9—N2—N1	117.28 (17)	O2—C9—N2	122.7 (2)
C9—N2—H2	118.8 (16)	O2—C9—C10	122.1 (2)
N1—N2—H2	120.2 (17)	N2—C9—C10	115.14 (18)
C6—C1—C2	117.4 (2)	C15—C10—C11	120.0 (2)
C6—C1—C7	121.3 (2)	C15—C10—C9	122.46 (19)
C2—C1—C7	121.4 (2)	C11—C10—C9	117.50 (18)
O1—C2—C3	117.3 (2)	C12—C11—C10	120.0 (2)
O1—C2—C1	123.3 (2)	C12—C11—H11	120.0
C3—C2—C1	119.3 (2)	C10—C11—H11	120.0
C4—C3—C2	121.6 (3)	O3—C12—C11	124.7 (2)
C4—C3—H3	119.2	O3—C12—C13	115.2 (2)
C2—C3—H3	119.2	C11—C12—C13	120.0 (2)
C3—C4—C5	120.0 (3)	C14—C13—C12	120.0 (2)
C3—C4—H4	120.0	C14—C13—H13	120.0
C5—C4—H4	120.0	C12—C13—H13	120.0
C4—C5—C6	119.5 (3)	C13—C14—C15	120.9 (2)
C4—C5—H5	120.2	C13—C14—H14	119.6
C6—C5—H5	120.2	C15—C14—H14	119.6
C5—C6—C1	122.2 (2)	C10—C15—C14	119.1 (2)
C5—C6—H6	118.9	C10—C15—H15	120.5
C1—C6—H6	118.9	C14—C15—H15	120.5
N1—C7—C1	115.99 (19)	O3—C16—H16A	109.5
N1—C7—C8	123.94 (19)	O3—C16—H16B	109.5
C1—C7—C8	120.07 (19)	H16A—C16—H16B	109.5
C7—C8—H8A	109.5	O3—C16—H16C	109.5
C7—C8—H8B	109.5	H16A—C16—H16C	109.5
H8A—C8—H8B	109.5	H16B—C16—H16C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2i	0.90 (1)	2.01 (1)	2.894 (2)	168 (2)
O1—H1···N1	0.82	1.82	2.534 (2)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2i	0.897 (10)	2.010 (11)	2.894 (2)	168 (2)
O1—H1⋯N1	0.82	1.82	2.534 (2)	145

Symmetry code: (i) .