N′-(2-Hydroxy­benzyl­idene)-4-methoxy­benzohydrazide

Tang, C.-B.

doi:10.1107/S1600536808008088

organic compounds

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Volume 64| Part 4| April 2008| Page o767

doi:10.1107/S1600536808008088

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N′-(2-Hydroxybenzylidene)-4-methoxybenzohydrazide

Chun-Bao Tang ^a ^*

^aDepartment of Chemistry, Jiaying University, Meizhou 514015, People's Republic of China
^*Correspondence e-mail: chunbao_tang@163.com

(Received 19 March 2008; accepted 25 March 2008; online 29 March 2008)

The title Schiff base compound, C₁₅H₁₄N₂O₃, was derived from the condensation reaction of salicylaldehyde with 4-methoxybenzohydrazide. The dihedral angle between the two benzene rings is 2.5 (2)°. In the crystal structure, molecules are linked through intermolecular N—H⋯O hydrogen bonds, forming chains running along the b axis.

Related literature

For related structures, see: Tang (2006 , 2007a ,b ,c ,d ). For reference structural data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₅H₁₄N₂O₃
M_r = 270.28
Monoclinic, P 2₁ /c
a = 16.283 (4) Å
b = 5.1876 (12) Å
c = 16.303 (4) Å
β = 108.093 (2)°
V = 1309.0 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 (2) K
0.23 × 0.20 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.978, T_max = 0.984
7166 measured reflections
2862 independent reflections
2288 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.111
S = 1.03
2862 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.14 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	2.18	3.0112 (15)	153
O1—H1⋯N1	0.82	1.90	2.6171 (14)	146
Symmetry code: (i) x, y+1, z.

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/S1600536808008088/sj2477sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808008088/sj2477Isup2.hkl

checkCIF report

Comment top

Recently, the author has reported the structures of several Schiff base compounds (Tang, 2006, 2007a,b,c,d) and, in continuation of work in this area, reports herein the structure of the title compound, (I), Fig. 1, a new Schiff base compound.

In the title compound (Fig. 1), the dihedral angle between the two benzene rings is 2.5 (2)°. The torsion angles C1—C7—N1—N2, C7—N1—N2—C8, and N1—N2—C8—C9 are 1.3 (2), 11.4 (2), and 0.6 (2)°, respectively. All the bond lengths are within normal values (Allen et al., 1987).

In the crystal structure of the compound, molecules are linked through N—H···O intermolecular hydrogen bonds (Table 1), forming chains running along the b axis (Fig. 2).

Related literature top

For related structures, see: Tang (2006, 2007a,b,c,d). For reference structural data, see: Allen et al. (1987).

Experimental top

Salicylaldehyde (0.1 mmol, 12.2 mg) and 4-methoxybenzohydrazide (0.1 mmol, 16.6 mg) were dissolved in an ethanol solution (20 ml). The mixture was stirred at reflux for 10 min to give a clear colorless solution. Colorless needle-like 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.
	Fig. 2. Molecular packing of (I) with hydrogen bonds drawn as dashed lines.

N'-(2-Hydroxybenzylidene)-4-methoxybenzohydrazide top

Crystal data top

C₁₅H₁₄N₂O₃	F(000) = 568
M_r = 270.28	D_x = 1.371 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2841 reflections
a = 16.283 (4) Å	θ = 2.5–28.4°
b = 5.1876 (12) Å	µ = 0.10 mm⁻¹
c = 16.303 (4) Å	T = 298 K
β = 108.093 (2)°	Cut from a needle, colorless
V = 1309.0 (5) Å³	0.23 × 0.20 × 0.17 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2862 independent reflections
Radiation source: fine-focus sealed tube	2288 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ω scans	θ_max = 27.0°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→17
T_min = 0.978, T_max = 0.984	k = −6→5
7166 measured reflections	l = −20→20

Refinement top

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)] = 0.038	H-atom parameters constrained
wR(F²) = 0.111	w = 1/[σ²(F_o²) + (0.0543P)² + 0.1695P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
2862 reflections	Δρ_max = 0.19 e Å⁻³
183 parameters	Δρ_min = −0.14 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0102 (19)

Crystal data top

C₁₅H₁₄N₂O₃	V = 1309.0 (5) Å³
M_r = 270.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.283 (4) Å	µ = 0.10 mm⁻¹
b = 5.1876 (12) Å	T = 298 K
c = 16.303 (4) Å	0.23 × 0.20 × 0.17 mm
β = 108.093 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2862 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2288 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.984	R_int = 0.024
7166 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.111	H-atom parameters constrained
S = 1.03	Δρ_max = 0.19 e Å⁻³
2862 reflections	Δρ_min = −0.14 e Å⁻³
183 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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	0.28687 (6)	0.79939 (18)	0.04446 (6)	0.0589 (3)
H1	0.2415	0.8168	0.0558	0.071*
O2	0.07668 (6)	0.61484 (17)	0.09720 (6)	0.0513 (3)
O3	−0.28125 (6)	0.8712 (2)	0.15298 (7)	0.0603 (3)
N1	0.18099 (6)	1.0151 (2)	0.11628 (7)	0.0458 (3)
N2	0.09898 (6)	1.0412 (2)	0.12266 (7)	0.0458 (3)
H2	0.0786	1.2025	0.1239	0.055*
C1	0.32018 (7)	1.1824 (2)	0.13304 (8)	0.0418 (3)
C2	0.34309 (8)	0.9849 (2)	0.08499 (8)	0.0447 (3)
C3	0.42580 (9)	0.9783 (3)	0.07764 (9)	0.0539 (3)
H3	0.4407	0.8497	0.0451	0.065*
C4	0.48579 (9)	1.1612 (3)	0.11825 (9)	0.0564 (4)
H4A	0.5410	1.1548	0.1129	0.068*
C5	0.46509 (9)	1.3546 (3)	0.16693 (9)	0.0559 (4)
H5	0.5063	1.4758	0.1950	0.067*
C6	0.38275 (8)	1.3652 (3)	0.17323 (8)	0.0497 (3)
H6	0.3685	1.4972	0.2050	0.060*
C7	0.23383 (8)	1.2025 (2)	0.14075 (8)	0.0448 (3)
H7	0.2172	1.3510	0.1634	0.054*
C8	0.04904 (7)	0.8257 (2)	0.11109 (7)	0.0393 (3)
C9	−0.03888 (7)	0.8543 (2)	0.11895 (7)	0.0376 (3)
C10	−0.06242 (8)	1.0470 (2)	0.16743 (8)	0.0439 (3)
H10	−0.0232	1.1763	0.1929	0.053*
C11	−0.14321 (8)	1.0465 (2)	0.17758 (8)	0.0475 (3)
H11	−0.1580	1.1738	0.2106	0.057*
C12	−0.20273 (8)	0.8575 (2)	0.13885 (8)	0.0438 (3)
C13	−0.18097 (8)	0.6676 (2)	0.08943 (8)	0.0465 (3)
H13	−0.2209	0.5417	0.0626	0.056*
C14	−0.09942 (8)	0.6672 (2)	0.08042 (8)	0.0436 (3)
H14	−0.0847	0.5386	0.0478	0.052*
C15	−0.33848 (9)	0.6588 (3)	0.12432 (11)	0.0682 (4)
H15A	−0.3531	0.6430	0.0628	0.102*
H15B	−0.3901	0.6869	0.1397	0.102*
H15C	−0.3108	0.5034	0.1511	0.102*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0530 (6)	0.0498 (6)	0.0720 (6)	−0.0030 (4)	0.0166 (5)	−0.0180 (5)
O2	0.0492 (5)	0.0387 (5)	0.0677 (6)	0.0032 (4)	0.0206 (4)	−0.0064 (4)
O3	0.0521 (6)	0.0612 (6)	0.0769 (7)	−0.0039 (5)	0.0339 (5)	−0.0048 (5)
N1	0.0397 (5)	0.0411 (6)	0.0572 (6)	0.0003 (4)	0.0159 (5)	0.0006 (5)
N2	0.0392 (5)	0.0368 (6)	0.0628 (7)	0.0017 (4)	0.0180 (5)	−0.0017 (5)
C1	0.0423 (6)	0.0367 (6)	0.0455 (6)	−0.0002 (5)	0.0123 (5)	0.0029 (5)
C2	0.0471 (7)	0.0398 (7)	0.0455 (7)	0.0003 (5)	0.0118 (5)	0.0016 (5)
C3	0.0568 (8)	0.0536 (8)	0.0565 (8)	0.0054 (6)	0.0250 (6)	−0.0013 (6)
C4	0.0476 (7)	0.0623 (9)	0.0647 (8)	−0.0017 (6)	0.0253 (6)	0.0080 (7)
C5	0.0494 (7)	0.0522 (8)	0.0650 (8)	−0.0130 (6)	0.0163 (6)	0.0007 (7)
C6	0.0505 (7)	0.0422 (7)	0.0561 (8)	−0.0051 (6)	0.0163 (6)	−0.0040 (6)
C7	0.0451 (7)	0.0390 (7)	0.0499 (7)	0.0019 (5)	0.0141 (5)	−0.0020 (5)
C8	0.0421 (6)	0.0361 (6)	0.0382 (6)	0.0018 (5)	0.0102 (5)	−0.0005 (5)
C9	0.0418 (6)	0.0334 (6)	0.0368 (6)	0.0006 (5)	0.0111 (5)	0.0014 (4)
C10	0.0487 (7)	0.0356 (6)	0.0466 (7)	−0.0034 (5)	0.0134 (5)	−0.0069 (5)
C11	0.0556 (7)	0.0409 (7)	0.0505 (7)	0.0012 (6)	0.0229 (6)	−0.0074 (5)
C12	0.0444 (6)	0.0449 (7)	0.0455 (6)	0.0015 (5)	0.0187 (5)	0.0046 (5)
C13	0.0456 (7)	0.0434 (7)	0.0494 (7)	−0.0079 (5)	0.0131 (5)	−0.0063 (5)
C14	0.0490 (7)	0.0380 (7)	0.0451 (6)	−0.0019 (5)	0.0165 (5)	−0.0068 (5)
C15	0.0492 (8)	0.0726 (11)	0.0883 (11)	−0.0098 (7)	0.0293 (8)	0.0025 (8)

Geometric parameters (Å, º) top

O1—C2	1.3509 (15)	C5—H5	0.9300
O1—H1	0.8200	C6—H6	0.9300
O2—C8	1.2303 (14)	C7—H7	0.9300
O3—C12	1.3695 (14)	C8—C9	1.4839 (16)
O3—C15	1.4248 (17)	C9—C14	1.3870 (16)
N1—C7	1.2773 (16)	C9—C10	1.3997 (16)
N1—N2	1.3780 (14)	C10—C11	1.3759 (17)
N2—C8	1.3604 (15)	C10—H10	0.9300
N2—H2	0.9000	C11—C12	1.3854 (17)
C1—C6	1.3974 (17)	C11—H11	0.9300
C1—C2	1.4085 (17)	C12—C13	1.3864 (17)
C1—C7	1.4538 (16)	C13—C14	1.3805 (17)
C2—C3	1.3891 (17)	C13—H13	0.9300
C3—C4	1.3750 (19)	C14—H14	0.9300
C3—H3	0.9300	C15—H15A	0.9600
C4—C5	1.384 (2)	C15—H15B	0.9600
C4—H4A	0.9300	C15—H15C	0.9600
C5—C6	1.3772 (18)

C2—O1—H1	109.4	O2—C8—N2	121.27 (11)
C12—O3—C15	117.01 (11)	O2—C8—C9	121.51 (10)
C7—N1—N2	118.44 (11)	N2—C8—C9	117.19 (10)
C8—N2—N1	117.41 (10)	C14—C9—C10	118.34 (11)
C8—N2—H2	123.9	C14—C9—C8	117.39 (10)
N1—N2—H2	117.6	C10—C9—C8	124.13 (10)
C6—C1—C2	118.30 (11)	C11—C10—C9	120.40 (11)
C6—C1—C7	119.64 (11)	C11—C10—H10	119.8
C2—C1—C7	122.06 (11)	C9—C10—H10	119.8
O1—C2—C3	117.92 (11)	C10—C11—C12	120.42 (11)
O1—C2—C1	122.26 (11)	C10—C11—H11	119.8
C3—C2—C1	119.82 (12)	C12—C11—H11	119.8
C4—C3—C2	120.29 (13)	O3—C12—C11	116.36 (11)
C4—C3—H3	119.9	O3—C12—C13	123.72 (11)
C2—C3—H3	119.9	C11—C12—C13	119.92 (11)
C3—C4—C5	120.86 (12)	C14—C13—C12	119.39 (11)
C3—C4—H4A	119.6	C14—C13—H13	120.3
C5—C4—H4A	119.6	C12—C13—H13	120.3
C6—C5—C4	119.20 (12)	C13—C14—C9	121.52 (11)
C6—C5—H5	120.4	C13—C14—H14	119.2
C4—C5—H5	120.4	C9—C14—H14	119.2
C5—C6—C1	121.51 (12)	O3—C15—H15A	109.5
C5—C6—H6	119.2	O3—C15—H15B	109.5
C1—C6—H6	119.2	H15A—C15—H15B	109.5
N1—C7—C1	119.60 (11)	O3—C15—H15C	109.5
N1—C7—H7	120.2	H15A—C15—H15C	109.5
C1—C7—H7	120.2	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	2.18	3.0112 (15)	153
O1—H1···N1	0.82	1.90	2.6171 (14)	146

Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₄N₂O₃
M_r	270.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	16.283 (4), 5.1876 (12), 16.303 (4)
β (°)	108.093 (2)
V (Å³)	1309.0 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.23 × 0.20 × 0.17

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.978, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	7166, 2862, 2288
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.111, 1.03
No. of reflections	2862
No. of parameters	183
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.14

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	0.90	2.18	3.0112 (15)	152.6
O1—H1···N1	0.82	1.90	2.6171 (14)	145.7

Symmetry code: (i) x, y+1, z.

Acknowledgements

Financial support from the Jiaying University Research Fund is gratefully acknowledged.

References

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