N′-(2,3-Dimethoxy­benzyl­idene)-2-hydr­oxy-3-methyl­benzohydrazide

Han, Y.-Y.; Zhao, Q.-R.

doi:10.1107/S1600536810012122

organic compounds

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ISSN: 2056-9890

Volume 66| Part 5| May 2010| Page o1026

https://doi.org/10.1107/S1600536810012122

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N′-(2,3-Dimethoxybenzylidene)-2-hydroxy-3-methylbenzohydrazide

You-Yue Han ^a ^* and Qiu-Rong Zhao ^a

^aDepartment of Chemistry and Life Science, Chuzhou University, Chuzhou, Anhui 239000, People's Republic of China
^*Correspondence e-mail: hanyouyue@126.com

(Received 30 March 2010; accepted 30 March 2010; online 2 April 2010)

In the title compound, C₁₇H₁₈N₂O₄, the dihedral angle between the two benzene rings is 6.0 (2)° and the molecule adopts an E configuration with respect to the C=N bond. There is an intramolecular O—H⋯O hydrogen bond in the molecule, which generates an S(6) ring. In the crystal, molecules are linked through intermolecular 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_r = 314.33
Orthorhombic, P c c n
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[F² > 2σ(F²)] = 0.067
wR(F²) = 0.175
S = 0.92
3461 reflections
211 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.30 e Å⁻³

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) $[-x+{\script{3\over 2}}, y, z-{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810012122/hb5386sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810012122/hb5386Isup2.hkl

checkCIF report

Comment top

As part of our ongoing studies of hydrazones (Han & Zhao, 2010), we now report the structure of the title compound, (I).

In the molecule of the title compound, Fig. 1, the dihedral angle between the two benzene rings is 6.0 (2)°. The molecule adopts an E configuration with respect to the C═N bond. There is an intramolecular O–H···O hydrogen bond (Table 1) in the molecule. All the bond lengths are within normal ranges (Allen et al., 1987).

In the crystal structure, molecules are linked through intermolecular N–H···O hydrogen bonds (Table 1) to form chains running along the c axis (Fig. 2).

Related literature top

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

Experimental top

A mixture of 2,3-dimethoxybenzaldehyde (0.166 g, 1 mmol) and 2-hydroxy-3-methylbenzohydrazide (0.166 g, 1 mmol) in 50 ml me thanol was stirred at room temperature for 1 h. The mixture was filtered to remove impurities, and then left at room temperature. After a few days, colourless blocks of (I) were formed.

Structure description top

As part of our ongoing studies of hydrazones (Han & Zhao, 2010), we now report the structure of the title compound, (I).

In the crystal structure, molecules are linked through intermolecular N–H···O hydrogen bonds (Table 1) to form chains running along the c axis (Fig. 2).

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

Computing details top

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

Figures top

	Fig. 1. The molecular structure of (I) with 30% probability displacement ellipsoids for non-H atoms. Intramolecular O–H···O hydrogen bond is shown as a dashed line.
	Fig. 2. The molecular packing of the title compound, viewed along the a axis. Hydrogen bonds are shown as dashed lines.

N'-(2,3-Dimethoxybenzylidene)-2-hydroxy-3-methylbenzohydrazide top

Crystal data top

C₁₇H₁₈N₂O₄	F(000) = 1328
M_r = 314.33	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0754P)²] where P = (F_o² + 2F_c²)/3
3461 reflections	(Δ/σ)_max = 0.001
211 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₇H₁₈N₂O₄	V = 3174.0 (11) Å³
M_r = 314.33	Z = 8
Orthorhombic, Pccn	Mo Kα radiation
a = 14.923 (3) Å	µ = 0.10 mm⁻¹
b = 24.329 (5) Å	T = 298 K
c = 8.7422 (17) Å	0.17 × 0.15 × 0.15 mm

Data collection top

Bruker SMART CCD diffractometer	3461 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1998 reflections with I > 2σ(I)
T_min = 0.984, T_max = 0.986	R_int = 0.223
17128 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	0 restraints
wR(F²) = 0.175	H-atom parameters constrained
S = 0.92	Δρ_max = 0.23 e Å⁻³
3461 reflections	Δρ_min = −0.30 e Å⁻³
211 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) −x+3/2, y, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₈N₂O₄
M_r	314.33
Crystal system, space group	Orthorhombic, Pccn
Temperature (K)	298
a, b, c (Å)	14.923 (3), 24.329 (5), 8.7422 (17)
V (Å³)	3174.0 (11)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.17 × 0.15 × 0.15

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.984, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	17128, 3461, 1998
R_int	0.223
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.175, 0.92
No. of reflections	3461
No. of parameters	211
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.30

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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) −x+3/2, y, z−1/2.

Acknowledgements

This work was supported by the Applied Chemistry Key Subject of Anhui Province (No. 200802187 C). The authors thank Mr Yuan-Guang Zhang of Anqing Normal University for his help with growing the crystals.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Han, Y.-Y. & Zhao, Q.-R. (2010). Acta Cryst. E66, o1025. Web of Science CSD CrossRef IUCr Journals Google Scholar
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