N′-(4-Hy­droxy­benzyl­idene)-3-meth­oxy­benzohydrazide

Tang, C.-B.

doi:10.1107/S1600536811055565

organic compounds

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Volume 68| Part 2| February 2012| Page o296

doi:10.1107/S1600536811055565

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N′-(4-Hydroxybenzylidene)-3-methoxybenzohydrazide

Chun-Bao Tang ^a ^*

^aDepartment of Chemistry, Jiaying University, Meizhou 514015, People's Republic of China
^*Correspondence e-mail: chunbao_tang@yahoo.cn

(Received 24 December 2011; accepted 24 December 2011; online 7 January 2012)

In the title compound, C₁₅H₁₄N₂O₃, the dihedral angle between the two benzene rings is 47.9 (3)°. In the crystal, molecules are linked through N—H⋯O, O—H⋯O and O—H⋯N hydrogen bonds, forming layers parallel to the ab plane.

Related literature

For general background to hydrazones, see: Rasras et al. (2010 ); Pyta et al. (2010 ); Angelusiu et al. (2010 ). For related structures, see: Fun et al. (2008 ); Singh & Singh (2010 ); Ahmad et al. (2010 ); Tang (2010 , 2011 ). For reference bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₅H₁₄N₂O₃
M_r = 270.28
Orthorhombic, P b c a
a = 13.221 (2) Å
b = 9.5336 (18) Å
c = 21.620 (2) Å
V = 2725.1 (7) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.23 × 0.21 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.979, T_max = 0.982
18234 measured reflections
2531 independent reflections
1805 reflections with I > 2σ(I)
R_int = 0.069

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.117
S = 1.11
2531 reflections
188 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2ⁱ	0.90 (1)	2.13 (1)	3.000 (2)	162 (3)
O1—H1⋯N1ⁱⁱ	0.85 (1)	2.11 (1)	2.959 (2)	176 (3)
O1—H1⋯O2ⁱⁱ	0.85 (1)	2.53 (3)	2.969 (2)	113 (3)
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) $[x+{\script{1\over 2}}, y, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811055565/cv5225sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811055565/cv5225Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811055565/cv5225Isup3.cml

checkCIF report

Comment top

Hydrazone compounds have received much attention in biological and structural chemistry in the last years (Rasras et al., 2010; Pyta et al., 2010; Angelusiu et al., 2010; Fun et al., 2008; Singh & Singh, 2010; Ahmad et al., 2010). As a continuation of our work on the structural study on such compounds (Tang, 2010, 2011), the author reports herein the crystal structure of the title new hydrazone compound (Fig. 1).

In the molecule of the title compound, the dihedral angle between the two benzene rings is 47.9 (3)°. Bond lengths in the compound are normal (Allen et al., 1987) and comparable to those in the similar compounds the author reported previously. In the crystal structure, molecules are linked through intermolecular N—H···O, O—H···O, and O—H···N hydrogen bonds (Table 1), forming layers parallel to the ab plane.

Related literature top

For general background to hydrazones, see: Rasras et al. (2010); Pyta et al. (2010); Angelusiu et al. (2010). For related structures, see: Fun et al. (2008); Singh & Singh (2010); Ahmad et al. (2010); Tang (2010, 2011). For reference bond-length data, see: Allen et al. (1987).

Experimental top

4-Hydroxybenzaldehyde (0.1 mmol, 12.2 mg) and 3-methoxybenzohydrazide (0.1 mmol, 16.6 mg) were dissolved in methanol (20 ml). The mixture was stirred at reflux for 10 min to give a clear colourless solution. Colourless needle-shaped crystals of the compound were formed by slow evaporation of the solvent over several days.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

N'-(4-Hydroxybenzylidene)-3-methoxybenzohydrazide top

Crystal data top

C₁₅H₁₄N₂O₃	D_x = 1.318 Mg m⁻³
M_r = 270.28	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 2706 reflections
a = 13.221 (2) Å	θ = 2.4–24.6°
b = 9.5336 (18) Å	µ = 0.09 mm⁻¹
c = 21.620 (2) Å	T = 298 K
V = 2725.1 (7) Å³	Cut from needle, colorless
Z = 8	0.23 × 0.21 × 0.20 mm
F(000) = 1136

Data collection top

Bruker SMART CCD area-detector diffractometer	2531 independent reflections
Radiation source: fine-focus sealed tube	1805 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.069
ω scans	θ_max = 25.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→16
T_min = 0.979, T_max = 0.982	k = −11→11
18234 measured reflections	l = −22→26

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ²(F_o²) + (0.041P)² + 0.712P] where P = (F_o² + 2F_c²)/3
2531 reflections	(Δ/σ)_max < 0.001
188 parameters	Δρ_max = 0.18 e Å⁻³
2 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₅H₁₄N₂O₃	V = 2725.1 (7) Å³
M_r = 270.28	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 13.221 (2) Å	µ = 0.09 mm⁻¹
b = 9.5336 (18) Å	T = 298 K
c = 21.620 (2) Å	0.23 × 0.21 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2531 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1805 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.982	R_int = 0.069
18234 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	2 restraints
wR(F²) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	Δρ_max = 0.18 e Å⁻³
2531 reflections	Δρ_min = −0.20 e Å⁻³
188 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 > 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.

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

	x	y	z	U_iso*/U_eq
N1	0.84363 (13)	0.96516 (19)	0.63698 (8)	0.0335 (5)
N2	0.76637 (13)	0.89157 (18)	0.60808 (9)	0.0331 (5)
O1	1.24869 (13)	1.15604 (17)	0.77207 (8)	0.0491 (5)
O2	0.67126 (11)	1.08925 (16)	0.60246 (8)	0.0416 (4)
O3	0.31857 (12)	0.8832 (2)	0.55817 (10)	0.0676 (6)
C1	1.00898 (16)	0.9639 (2)	0.68058 (11)	0.0327 (5)
C2	1.02194 (17)	1.1091 (2)	0.67981 (12)	0.0390 (6)
H2A	0.9757	1.1648	0.6586	0.047*
C3	1.10217 (17)	1.1714 (2)	0.70994 (11)	0.0414 (6)
H3	1.1102	1.2682	0.7084	0.050*
C4	1.17085 (16)	1.0898 (2)	0.74251 (11)	0.0340 (6)
C5	1.16016 (17)	0.9463 (2)	0.74303 (11)	0.0378 (6)
H5	1.2064	0.8911	0.7645	0.045*
C6	1.08096 (16)	0.8842 (2)	0.71180 (12)	0.0384 (6)
H6	1.0755	0.7869	0.7116	0.046*
C7	0.92309 (16)	0.8958 (2)	0.65072 (11)	0.0338 (6)
H7	0.9263	0.8005	0.6416	0.041*
C8	0.68050 (16)	0.9628 (2)	0.59326 (10)	0.0311 (5)
C9	0.59785 (15)	0.8768 (2)	0.56562 (10)	0.0300 (5)
C10	0.49867 (16)	0.9232 (2)	0.57510 (11)	0.0365 (6)
H10	0.4868	1.0042	0.5980	0.044*
C11	0.41857 (17)	0.8491 (3)	0.55060 (12)	0.0429 (6)
C12	0.43747 (19)	0.7307 (3)	0.51536 (13)	0.0495 (7)
H12	0.3837	0.6808	0.4985	0.059*
C13	0.53502 (19)	0.6863 (3)	0.50505 (12)	0.0463 (7)
H13	0.5467	0.6076	0.4807	0.056*
C14	0.61629 (17)	0.7580 (2)	0.53071 (10)	0.0375 (6)
H14	0.6821	0.7266	0.5245	0.045*
C15	0.2946 (2)	1.0000 (4)	0.59606 (15)	0.0752 (10)
H15A	0.3231	0.9867	0.6365	0.113*
H15B	0.2224	1.0087	0.5994	0.113*
H15C	0.3219	1.0838	0.5779	0.113*
H2	0.770 (2)	0.7974 (11)	0.6051 (14)	0.090*
H1	1.276 (2)	1.104 (3)	0.7996 (13)	0.113*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0297 (10)	0.0310 (10)	0.0398 (12)	−0.0013 (9)	−0.0022 (9)	−0.0029 (9)
N2	0.0288 (10)	0.0267 (10)	0.0439 (12)	−0.0026 (9)	−0.0047 (9)	−0.0049 (9)
O1	0.0510 (10)	0.0357 (10)	0.0607 (13)	−0.0157 (8)	−0.0214 (10)	0.0127 (9)
O2	0.0395 (9)	0.0267 (9)	0.0587 (12)	0.0026 (7)	−0.0059 (8)	−0.0060 (8)
O3	0.0298 (10)	0.0944 (16)	0.0784 (15)	−0.0011 (10)	−0.0039 (10)	−0.0058 (13)
C1	0.0298 (12)	0.0289 (12)	0.0393 (14)	0.0024 (10)	0.0001 (11)	0.0002 (11)
C2	0.0347 (13)	0.0336 (13)	0.0486 (16)	0.0032 (11)	−0.0085 (11)	0.0082 (12)
C3	0.0468 (15)	0.0241 (12)	0.0532 (17)	−0.0039 (11)	−0.0067 (13)	0.0065 (12)
C4	0.0332 (12)	0.0319 (12)	0.0370 (14)	−0.0054 (10)	−0.0027 (11)	0.0053 (11)
C5	0.0375 (13)	0.0275 (12)	0.0483 (16)	0.0020 (10)	−0.0085 (12)	0.0070 (11)
C6	0.0391 (13)	0.0218 (12)	0.0544 (17)	−0.0015 (10)	−0.0041 (12)	0.0001 (11)
C7	0.0346 (13)	0.0261 (12)	0.0406 (15)	−0.0007 (10)	−0.0007 (11)	−0.0012 (11)
C8	0.0320 (12)	0.0305 (13)	0.0307 (14)	0.0004 (10)	0.0033 (10)	0.0018 (11)
C9	0.0305 (12)	0.0274 (12)	0.0322 (14)	−0.0029 (9)	−0.0020 (10)	0.0049 (11)
C10	0.0357 (13)	0.0350 (13)	0.0389 (15)	0.0000 (10)	−0.0014 (11)	0.0012 (11)
C11	0.0317 (13)	0.0542 (16)	0.0427 (16)	−0.0045 (12)	−0.0032 (12)	0.0085 (13)
C12	0.0420 (15)	0.0547 (17)	0.0518 (18)	−0.0145 (13)	−0.0148 (13)	0.0015 (14)
C13	0.0521 (16)	0.0382 (14)	0.0486 (17)	−0.0050 (12)	−0.0090 (14)	−0.0092 (12)
C14	0.0356 (13)	0.0344 (13)	0.0426 (15)	−0.0008 (11)	−0.0021 (11)	−0.0028 (12)
C15	0.0442 (17)	0.107 (3)	0.074 (2)	0.0198 (17)	0.0123 (16)	0.008 (2)

Geometric parameters (Å, º) top

N1—C7	1.277 (3)	C5—H5	0.9300
N1—N2	1.388 (2)	C6—H6	0.9300
N2—C8	1.361 (3)	C7—H7	0.9300
N2—H2	0.901 (10)	C8—C9	1.491 (3)
O1—C4	1.366 (3)	C9—C14	1.382 (3)
O1—H1	0.853 (10)	C9—C10	1.399 (3)
O2—C8	1.228 (2)	C10—C11	1.379 (3)
O3—C11	1.371 (3)	C10—H10	0.9300
O3—C15	1.419 (3)	C11—C12	1.384 (4)
C1—C6	1.392 (3)	C12—C13	1.376 (3)
C1—C2	1.395 (3)	C12—H12	0.9300
C1—C7	1.459 (3)	C13—C14	1.389 (3)
C2—C3	1.379 (3)	C13—H13	0.9300
C2—H2A	0.9300	C14—H14	0.9300
C3—C4	1.387 (3)	C15—H15A	0.9600
C3—H3	0.9300	C15—H15B	0.9600
C4—C5	1.376 (3)	C15—H15C	0.9600
C5—C6	1.379 (3)

C7—N1—N2	116.64 (18)	O2—C8—N2	122.3 (2)
C8—N2—N1	117.87 (17)	O2—C8—C9	122.15 (19)
C8—N2—H2	121.7 (19)	N2—C8—C9	115.51 (19)
N1—N2—H2	119.8 (19)	C14—C9—C10	120.3 (2)
C4—O1—H1	112 (2)	C14—C9—C8	122.69 (19)
C11—O3—C15	118.1 (2)	C10—C9—C8	117.0 (2)
C6—C1—C2	117.6 (2)	C11—C10—C9	120.1 (2)
C6—C1—C7	120.3 (2)	C11—C10—H10	120.0
C2—C1—C7	122.1 (2)	C9—C10—H10	120.0
C3—C2—C1	121.1 (2)	O3—C11—C10	125.0 (2)
C3—C2—H2A	119.5	O3—C11—C12	115.7 (2)
C1—C2—H2A	119.5	C10—C11—C12	119.4 (2)
C2—C3—C4	120.1 (2)	C13—C12—C11	120.6 (2)
C2—C3—H3	119.9	C13—C12—H12	119.7
C4—C3—H3	119.9	C11—C12—H12	119.7
O1—C4—C5	122.2 (2)	C12—C13—C14	120.6 (2)
O1—C4—C3	118.13 (19)	C12—C13—H13	119.7
C5—C4—C3	119.6 (2)	C14—C13—H13	119.7
C4—C5—C6	120.1 (2)	C9—C14—C13	119.0 (2)
C4—C5—H5	120.0	C9—C14—H14	120.5
C6—C5—H5	120.0	C13—C14—H14	120.5
C5—C6—C1	121.5 (2)	O3—C15—H15A	109.5
C5—C6—H6	119.3	O3—C15—H15B	109.5
C1—C6—H6	119.3	H15A—C15—H15B	109.5
N1—C7—C1	120.9 (2)	O3—C15—H15C	109.5
N1—C7—H7	119.6	H15A—C15—H15C	109.5
C1—C7—H7	119.6	H15B—C15—H15C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.90 (1)	2.13 (1)	3.000 (2)	162 (3)
O1—H1···N1ⁱⁱ	0.85 (1)	2.11 (1)	2.959 (2)	176 (3)
O1—H1···O2ⁱⁱ	0.85 (1)	2.53 (3)	2.969 (2)	113 (3)

Symmetry codes: (i) −x+3/2, y−1/2, z; (ii) x+1/2, y, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄N₂O₃
M_r	270.28
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	13.221 (2), 9.5336 (18), 21.620 (2)
V (Å³)	2725.1 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.23 × 0.21 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.979, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	18234, 2531, 1805
R_int	0.069
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.117, 1.11
No. of reflections	2531
No. of parameters	188
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.20

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.901 (10)	2.132 (13)	3.000 (2)	162 (3)
O1—H1···N1ⁱⁱ	0.853 (10)	2.107 (11)	2.959 (2)	176 (3)
O1—H1···O2ⁱⁱ	0.853 (10)	2.53 (3)	2.969 (2)	113 (3)

Symmetry codes: (i) −x+3/2, y−1/2, z; (ii) x+1/2, y, −z+3/2.

Acknowledgements

Financial support from the Jiaying University research fund is gratefully acknowledged.

References

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