N'-(2,3-Dimethoxy-benzyl-idene)-2-hydr-oxy-3-methyl-benzohydrazide.

In the title compound, C(17)H(18)N(2)O(4), the dihedral angle between the two benzene rings is 6.0 (2)° and the mol-ecule adopts an E configuration with respect to the C=N bond. There is an intra-molecular O-H⋯O hydrogen bond in the mol-ecule, which generates an S(6) ring. In the crystal, mol-ecules are linked through inter-molecular N-H⋯O hydrogen bonds, forming C(4) chains running along the c axis.

Related literature

For a related structure and background information, see: Han & Zhao (2010 ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C17H18N2O4

M = 314.33

Orthorhombic,

a = 14.923 (3) Å

b = 24.329 (5) Å

c = 8.7422 (17) Å

V = 3174.0 (11) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.17 × 0.15 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.984, T max = 0.986

17128 measured reflections

3461 independent reflections

1998 reflections with I > 2σ(I)

R int = 0.223

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.175

S = 0.92

3461 reflections

211 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.30 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAIn class="Chemical">NT; 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/S1600536810012122/hb5386sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012122/hb5386Isup2.hkl

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

C17H18N2O4	F(000) = 1328
Mr = 314.33	Dx = 1.316 Mg m−3
Orthorhombic, Pccn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 2994 reflections
a = 14.923 (3) Å	θ = 2.7–24.9°
b = 24.329 (5) Å	µ = 0.10 mm−1
c = 8.7422 (17) Å	T = 298 K
V = 3174.0 (11) Å3	Block, colorless
Z = 8	0.17 × 0.15 × 0.15 mm

Bruker SMART CCD diffractometer	3461 independent reflections
Radiation source: fine-focus sealed tube	1998 reflections with I > 2σ(I)
graphite	Rint = 0.223
ω scans	θmax = 27.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −18→18
Tmin = 0.984, Tmax = 0.986	k = −30→31
17128 measured reflections	l = −8→11

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.175	H-atom parameters constrained
S = 0.92	w = 1/[σ2(Fo2) + (0.0754P)2] where P = (Fo2 + 2Fc2)/3
3461 reflections	(Δ/σ)max = 0.001
211 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.30 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 > σ(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	0.42606 (9)	0.10101 (6)	0.37153 (16)	0.0482 (4)
O2	0.28300 (9)	0.06224 (8)	0.52262 (16)	0.0602 (5)
O3	0.84543 (10)	0.11847 (7)	0.62612 (16)	0.0586 (5)
O4	1.01095 (9)	0.13449 (7)	0.53290 (16)	0.0601 (5)
H4	0.9716	0.1232	0.5903	0.072*
N1	0.67827 (11)	0.09279 (7)	0.53655 (18)	0.0464 (5)
N2	0.74005 (11)	0.11742 (7)	0.44045 (19)	0.0474 (5)
H2A	0.7274	0.1235	0.3411	0.057*
C1	0.52468 (13)	0.06866 (8)	0.5673 (2)	0.0402 (5)
C2	0.43791 (13)	0.07538 (9)	0.5098 (2)	0.0396 (5)
C3	0.36482 (13)	0.05310 (9)	0.5889 (2)	0.0443 (5)
C4	0.37887 (16)	0.02333 (10)	0.7208 (2)	0.0521 (6)
H4A	0.3306	0.0079	0.7727	0.063*
C5	0.46507 (16)	0.01651 (10)	0.7758 (2)	0.0536 (6)
H5	0.4743	−0.0036	0.8649	0.064*
C6	0.53705 (15)	0.03885 (9)	0.7014 (2)	0.0473 (5)
H6	0.5945	0.0341	0.7406	0.057*
C7	0.38589 (19)	0.15360 (11)	0.3766 (3)	0.0724 (8)
H7A	0.3336	0.1523	0.4405	0.109*
H7B	0.3690	0.1646	0.2751	0.109*
H7C	0.4278	0.1797	0.4178	0.109*
C8	0.20603 (16)	0.04196 (12)	0.6008 (3)	0.0701 (8)
H8A	0.2071	0.0025	0.6009	0.105*
H8B	0.1529	0.0546	0.5500	0.105*
H8C	0.2063	0.0551	0.7043	0.105*
C9	0.59903 (13)	0.09237 (9)	0.4826 (2)	0.0445 (5)
H9	0.5885	0.1076	0.3867	0.053*
C10	0.82117 (13)	0.13106 (9)	0.4951 (2)	0.0428 (5)
C11	0.88015 (14)	0.16270 (8)	0.3910 (2)	0.0421 (5)
C12	0.97309 (14)	0.16251 (8)	0.4165 (2)	0.0456 (5)
C13	1.03102 (15)	0.19180 (10)	0.3209 (3)	0.0532 (6)
C14	0.99399 (18)	0.22279 (10)	0.2061 (3)	0.0650 (7)
H14	1.0318	0.2430	0.1429	0.078*
C15	0.90212 (19)	0.22521 (11)	0.1802 (3)	0.0671 (7)
H15	0.8789	0.2469	0.1021	0.081*
C16	0.84659 (15)	0.19497 (9)	0.2724 (2)	0.0538 (6)
H16	0.7851	0.1960	0.2554	0.065*
C17	1.13038 (15)	0.18931 (13)	0.3465 (3)	0.0768 (8)
H17A	1.1502	0.1519	0.3392	0.115*
H17B	1.1442	0.2034	0.4464	0.115*
H17C	1.1603	0.2111	0.2705	0.115*

	U11	U22	U33	U12	U13	U23
O1	0.0396 (8)	0.0589 (10)	0.0462 (9)	0.0034 (7)	−0.0010 (6)	0.0099 (7)
O2	0.0318 (8)	0.0918 (13)	0.0569 (10)	−0.0080 (8)	0.0014 (7)	0.0109 (8)
O3	0.0378 (8)	0.0921 (13)	0.0459 (9)	−0.0056 (8)	−0.0042 (7)	0.0152 (8)
O4	0.0370 (9)	0.0835 (12)	0.0597 (10)	0.0003 (8)	−0.0035 (7)	0.0124 (8)
N1	0.0348 (10)	0.0580 (12)	0.0463 (10)	−0.0030 (8)	−0.0004 (8)	0.0027 (8)
N2	0.0375 (10)	0.0623 (12)	0.0422 (10)	−0.0061 (9)	−0.0030 (8)	0.0055 (8)
C1	0.0371 (11)	0.0444 (12)	0.0390 (11)	−0.0017 (9)	−0.0027 (9)	−0.0038 (9)
C2	0.0373 (11)	0.0444 (11)	0.0372 (11)	−0.0011 (9)	−0.0012 (9)	0.0006 (9)
C3	0.0377 (12)	0.0543 (13)	0.0409 (11)	−0.0030 (10)	0.0018 (9)	−0.0034 (10)
C4	0.0520 (14)	0.0595 (15)	0.0448 (12)	−0.0075 (11)	0.0059 (11)	0.0020 (10)
C5	0.0616 (15)	0.0590 (14)	0.0403 (12)	0.0016 (12)	−0.0011 (11)	0.0102 (10)
C6	0.0470 (13)	0.0505 (13)	0.0445 (12)	0.0015 (10)	−0.0070 (10)	0.0015 (10)
C7	0.0754 (19)	0.0632 (18)	0.0787 (17)	0.0105 (14)	−0.0018 (15)	0.0187 (14)
C8	0.0411 (14)	0.102 (2)	0.0677 (16)	−0.0099 (13)	0.0149 (11)	−0.0004 (14)
C9	0.0368 (12)	0.0531 (13)	0.0436 (12)	0.0003 (9)	−0.0030 (9)	0.0007 (10)
C10	0.0348 (11)	0.0501 (12)	0.0437 (12)	0.0008 (10)	−0.0017 (9)	−0.0012 (9)
C11	0.0410 (12)	0.0432 (12)	0.0422 (11)	−0.0039 (9)	−0.0031 (9)	−0.0042 (9)
C12	0.0440 (13)	0.0456 (12)	0.0472 (12)	−0.0001 (10)	−0.0006 (10)	−0.0079 (10)
C13	0.0461 (13)	0.0532 (14)	0.0602 (14)	−0.0050 (11)	0.0092 (11)	−0.0077 (11)
C14	0.0723 (18)	0.0547 (15)	0.0680 (16)	−0.0191 (13)	0.0149 (14)	0.0024 (12)
C15	0.0768 (19)	0.0569 (16)	0.0678 (16)	−0.0098 (13)	−0.0064 (14)	0.0206 (12)
C16	0.0519 (13)	0.0512 (14)	0.0584 (14)	−0.0029 (11)	−0.0090 (11)	0.0061 (11)
C17	0.0450 (15)	0.087 (2)	0.098 (2)	−0.0091 (14)	0.0176 (14)	−0.0022 (16)

O1—C2	1.372 (2)	C7—H7A	0.9600
O1—C7	1.414 (3)	C7—H7B	0.9600
O2—C3	1.370 (2)	C7—H7C	0.9600
O2—C8	1.425 (3)	C8—H8A	0.9600
O3—C10	1.240 (2)	C8—H8B	0.9600
O4—C12	1.349 (2)	C8—H8C	0.9600
O4—H4	0.8195	C9—H9	0.9300
N1—C9	1.273 (3)	C10—C11	1.482 (3)
N1—N2	1.384 (2)	C11—C16	1.394 (3)
N2—C10	1.343 (2)	C11—C12	1.405 (3)
N2—H2A	0.9005	C12—C13	1.398 (3)
C1—C6	1.391 (3)	C13—C14	1.372 (3)
C1—C2	1.398 (3)	C13—C17	1.501 (3)
C1—C9	1.453 (3)	C14—C15	1.391 (4)
C2—C3	1.401 (3)	C14—H14	0.9300
C3—C4	1.378 (3)	C15—C16	1.370 (3)
C4—C5	1.383 (3)	C15—H15	0.9300
C4—H4A	0.9300	C16—H16	0.9300
C5—C6	1.368 (3)	C17—H17A	0.9600
C5—H5	0.9300	C17—H17B	0.9600
C6—H6	0.9300	C17—H17C	0.9600
C2—O1—C7	115.99 (16)	O2—C8—H8C	109.5
C3—O2—C8	117.34 (18)	H8A—C8—H8C	109.5
C12—O4—H4	109.3	H8B—C8—H8C	109.5
C9—N1—N2	113.41 (17)	N1—C9—C1	121.57 (19)
C10—N2—N1	119.45 (17)	N1—C9—H9	119.2
C10—N2—H2A	119.4	C1—C9—H9	119.2
N1—N2—H2A	121.1	O3—C10—N2	122.05 (19)
C6—C1—C2	119.12 (18)	O3—C10—C11	121.49 (18)
C6—C1—C9	122.34 (18)	N2—C10—C11	116.46 (17)
C2—C1—C9	118.53 (18)	C16—C11—C12	118.3 (2)
O1—C2—C1	119.28 (17)	C16—C11—C10	122.42 (19)
O1—C2—C3	120.71 (17)	C12—C11—C10	119.17 (18)
C1—C2—C3	119.90 (18)	O4—C12—C13	116.7 (2)
O2—C3—C4	125.12 (18)	O4—C12—C11	122.34 (19)
O2—C3—C2	114.99 (18)	C13—C12—C11	120.9 (2)
C4—C3—C2	119.87 (19)	C14—C13—C12	117.9 (2)
C3—C4—C5	119.7 (2)	C14—C13—C17	122.0 (2)
C3—C4—H4A	120.2	C12—C13—C17	120.1 (2)
C5—C4—H4A	120.2	C13—C14—C15	122.6 (2)
C6—C5—C4	121.1 (2)	C13—C14—H14	118.7
C6—C5—H5	119.4	C15—C14—H14	118.7
C4—C5—H5	119.4	C16—C15—C14	118.6 (2)
C5—C6—C1	120.25 (19)	C16—C15—H15	120.7
C5—C6—H6	119.9	C14—C15—H15	120.7
C1—C6—H6	119.9	C15—C16—C11	121.5 (2)
O1—C7—H7A	109.5	C15—C16—H16	119.2
O1—C7—H7B	109.5	C11—C16—H16	119.2
H7A—C7—H7B	109.5	C13—C17—H17A	109.5
O1—C7—H7C	109.5	C13—C17—H17B	109.5
H7A—C7—H7C	109.5	H17A—C17—H17B	109.5
H7B—C7—H7C	109.5	C13—C17—H17C	109.5
O2—C8—H8A	109.5	H17A—C17—H17C	109.5
O2—C8—H8B	109.5	H17B—C17—H17C	109.5
H8A—C8—H8B	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3	0.82	1.91	2.630 (2)	146
N2—H2A···O3i	0.90	2.17	3.030 (2)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O3	0.82	1.91	2.630 (2)	146
N2—H2A⋯O3i	0.90	2.17	3.030 (2)	158

Symmetry code: (i) .