N′-[4-(Dimethyl­amino)benzyl­idene]-3-hydroxy­benzohydrazide

Nie, Y.

doi:10.1107/S160053680800130X

organic compounds

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Volume 64| Part 2| February 2008| Page o471

doi:10.1107/S160053680800130X

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N′-[4-(Dimethylamino)benzylidene]-3-hydroxybenzohydrazide

Yi Nie ^a ^*

^aDepartment of Chemistry, Qufu Normal University, Qufu 273165, People's Republic of China
^*Correspondence e-mail: nieyi68@126.com

(Received 4 January 2008; accepted 13 January 2008; online 18 January 2008)

The title compound, C₁₆H₁₇N₃O₂, was synthesized by the reaction of 4-dimethylaminobenzaldehyde with 3-hydroxybenzoic acid hydrazide in methanol. The dihedral angle between the two benzene rings in the molecule is 9.2 (2)°. In the crystal structure, molecules are linked through intermolecular O—H⋯O, O—H⋯N and N—H⋯O hydrogen bonds, forming layers parallel to the bc plane.

Related literature

For related literature, see: Akitsu & Einaga (2006 ); Bahner et al. (1968 ); Butcher et al. (2005 ); Hodnett & Mooney (1970 ); Merchant & Chothia (1970 ); Pradeep (2005 ); Sigman & Jacobsen (1998 ).

Experimental

Crystal data

C₁₆H₁₇N₃O₂
M_r = 283.33
Monoclinic, P 2₁ /c
a = 13.397 (3) Å
b = 9.663 (2) Å
c = 11.183 (2) Å
β = 101.97 (3)°
V = 1416.2 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 (2) K
0.28 × 0.27 × 0.27 mm

Data collection

Bruker SMART APEX area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.975, T_max = 0.976
11531 measured reflections
3094 independent reflections
2579 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.130
S = 1.05
3094 reflections
196 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1ⁱ	0.82	2.18	2.8470 (14)	138
O2—H2⋯N2ⁱ	0.82	2.36	3.1008 (16)	150
N3—H3A⋯O1ⁱⁱ	0.895 (9)	2.561 (11)	3.4172 (16)	160.4 (16)
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); 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/S160053680800130X/su2040sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680800130X/su2040Isup2.hkl

checkCIF report

Comment top

Schiff base compounds have been widely investigated due to their easy synthesis, versatile structures and wide applications (Sigman & Jacobsen, 1998; Akitsu & Einaga, 2006; Pradeep, 2005; Butcher et al., 2005). The excellent antibacterial and antitumor properties of such compounds have attracted much interest in recent years (Hodnett & Mooney, 1970; Bahner et al., 1968; Merchant & Chothia, 1970). In order to investigate further the structures of such compounds, the new title Schiff base compound is reported on here.

The dihedral angle between the two benzene rings in the molecule (Fig. 1) of the title compound is 9.2 (2)°. In the crystal structure, molecules are linked through intermolecular O–H···O, O–H···N and N–H···O hydrogen bonds (Table 1), forming layers parallel to the bc plane (Fig. 2).

Related literature top

For related literature, see: Akitsu & Einaga (2006); Bahner et al. (1968); Butcher et al. (2005); Hodnett & Mooney (1970); Merchant & Chothia (1970); Pradeep (2005); Sigman & Jacobsen (1998).

Experimental top

The title compound was obtained by stirring of 4-dimethylaminobenzaldehyde (0.1 mmol, 14.9 mg) and 3-hydroxybenzoic acid hydrazide (0.1 mmol, 15.2 mg) in a methanol solution (10 ml) at room temperature. Yellow block-shaped single crystals suitable for X-ray diffraction were formed from the solution after seven days.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Version 5.1; Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom labelling scheme and displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Crystal packing of the title compound view along the a axis [hydrogen bonds are drawn as dotted lines].

N'-[4-(Dimethylamino)benzylidene]3-hydroxybenzohydrazide top

Crystal data top

C₁₆H₁₇N₃O₂	F(000) = 600
M_r = 283.33	D_x = 1.329 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4593 reflections
a = 13.397 (3) Å	θ = 2.5–27.7°
b = 9.663 (2) Å	µ = 0.09 mm⁻¹
c = 11.183 (2) Å	T = 298 K
β = 101.97 (3)°	Block, yellow
V = 1416.2 (5) Å³	0.28 × 0.27 × 0.27 mm
Z = 4

Data collection top

Bruker SMART APEX area-detector diffractometer	3094 independent reflections
Radiation source: fine-focus sealed tube	2579 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ω scans	θ_max = 27.0°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→17
T_min = 0.975, T_max = 0.976	k = −12→12
11531 measured reflections	l = −14→14

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0773P)² + 0.1729P] where P = (F_o² + 2F_c²)/3
3094 reflections	(Δ/σ)_max < 0.001
196 parameters	Δρ_max = 0.21 e Å⁻³
1 restraint	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₆H₁₇N₃O₂	V = 1416.2 (5) Å³
M_r = 283.33	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.397 (3) Å	µ = 0.09 mm⁻¹
b = 9.663 (2) Å	T = 298 K
c = 11.183 (2) Å	0.28 × 0.27 × 0.27 mm
β = 101.97 (3)°

Data collection top

Bruker SMART APEX area-detector diffractometer	3094 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2579 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.976	R_int = 0.021
11531 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	1 restraint
wR(F²) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.21 e Å⁻³
3094 reflections	Δρ_min = −0.29 e Å⁻³
196 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	0.51231 (8)	0.27675 (11)	0.29293 (9)	0.0574 (3)
O2	0.28657 (7)	0.69755 (10)	0.22473 (9)	0.0486 (3)
H2	0.3315	0.7006	0.1849	0.073*
N1	0.97117 (10)	−0.30631 (15)	0.63913 (13)	0.0654 (4)
N2	0.60441 (8)	0.13189 (10)	0.48763 (10)	0.0416 (3)
N3	0.52359 (8)	0.22033 (11)	0.49046 (10)	0.0420 (3)
C1	0.72192 (9)	−0.03254 (12)	0.59700 (11)	0.0379 (3)
C2	0.78863 (10)	−0.03161 (13)	0.51647 (11)	0.0430 (3)
H2A	0.7774	0.0302	0.4513	0.052*
C3	0.87041 (10)	−0.11981 (14)	0.53134 (12)	0.0445 (3)
H3	0.9138	−0.1157	0.4764	0.053*
C4	0.89036 (9)	−0.21613 (13)	0.62715 (12)	0.0425 (3)
C5	0.82405 (10)	−0.21577 (14)	0.70911 (12)	0.0456 (3)
H5	0.8352	−0.2770	0.7747	0.055*
C6	0.74284 (10)	−0.12595 (14)	0.69358 (11)	0.0424 (3)
H6	0.7004	−0.1277	0.7496	0.051*
C7	0.99119 (16)	−0.4061 (2)	0.73523 (17)	0.0793 (6)
H7A	1.0129	−0.3597	0.8121	0.119*
H7B	1.0439	−0.4679	0.7219	0.119*
H7C	0.9302	−0.4578	0.7363	0.119*
C8	1.04154 (15)	−0.2992 (2)	0.5584 (2)	0.0903 (7)
H8A	1.0063	−0.3194	0.4764	0.135*
H8B	1.0952	−0.3655	0.5835	0.135*
H8C	1.0702	−0.2079	0.5612	0.135*
C9	0.63422 (9)	0.05897 (13)	0.58348 (11)	0.0411 (3)
H9	0.5988	0.0645	0.6466	0.049*
C10	0.48449 (9)	0.29458 (12)	0.38962 (12)	0.0397 (3)
C11	0.40510 (9)	0.39961 (12)	0.40150 (11)	0.0375 (3)
C12	0.38258 (9)	0.49733 (12)	0.30887 (11)	0.0375 (3)
H12	0.4168	0.4954	0.2446	0.045*
C13	0.30939 (9)	0.59770 (12)	0.31174 (11)	0.0380 (3)
C14	0.25681 (10)	0.59887 (14)	0.40629 (12)	0.0453 (3)
H14	0.2067	0.6651	0.4080	0.054*
C15	0.27927 (11)	0.50121 (16)	0.49776 (13)	0.0530 (4)
H15	0.2440	0.5021	0.5611	0.064*
C16	0.35350 (10)	0.40181 (14)	0.49689 (12)	0.0469 (3)
H16	0.3686	0.3372	0.5596	0.056*
H3A	0.5095 (14)	0.2388 (19)	0.5637 (11)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0646 (6)	0.0592 (6)	0.0572 (6)	0.0197 (5)	0.0327 (5)	0.0044 (5)
O2	0.0480 (5)	0.0487 (5)	0.0530 (6)	0.0081 (4)	0.0192 (4)	0.0094 (4)
N1	0.0552 (7)	0.0751 (9)	0.0698 (8)	0.0289 (7)	0.0219 (6)	0.0220 (7)
N2	0.0369 (5)	0.0388 (6)	0.0501 (6)	0.0050 (4)	0.0114 (4)	−0.0082 (4)
N3	0.0380 (5)	0.0417 (6)	0.0485 (6)	0.0072 (4)	0.0137 (5)	−0.0065 (5)
C1	0.0368 (6)	0.0382 (6)	0.0391 (6)	−0.0001 (5)	0.0087 (5)	−0.0057 (5)
C2	0.0452 (7)	0.0451 (7)	0.0400 (6)	0.0056 (5)	0.0115 (5)	0.0069 (5)
C3	0.0427 (7)	0.0535 (8)	0.0407 (7)	0.0056 (5)	0.0162 (5)	0.0024 (5)
C4	0.0388 (6)	0.0447 (7)	0.0432 (7)	0.0046 (5)	0.0067 (5)	0.0001 (5)
C5	0.0467 (7)	0.0504 (7)	0.0397 (7)	0.0023 (6)	0.0085 (5)	0.0086 (5)
C6	0.0428 (7)	0.0499 (7)	0.0373 (6)	−0.0026 (5)	0.0149 (5)	−0.0027 (5)
C7	0.0834 (12)	0.0834 (13)	0.0713 (11)	0.0421 (10)	0.0162 (9)	0.0196 (9)
C8	0.0656 (11)	0.1028 (15)	0.1139 (16)	0.0410 (11)	0.0449 (11)	0.0305 (13)
C9	0.0394 (6)	0.0403 (6)	0.0456 (7)	0.0004 (5)	0.0131 (5)	−0.0074 (5)
C10	0.0359 (6)	0.0369 (6)	0.0497 (7)	0.0000 (5)	0.0165 (5)	−0.0046 (5)
C11	0.0332 (6)	0.0371 (6)	0.0442 (7)	−0.0012 (5)	0.0122 (5)	−0.0055 (5)
C12	0.0352 (6)	0.0394 (6)	0.0412 (6)	−0.0024 (5)	0.0156 (5)	−0.0044 (5)
C13	0.0345 (6)	0.0378 (6)	0.0423 (6)	−0.0024 (5)	0.0095 (5)	−0.0018 (5)
C14	0.0393 (6)	0.0472 (7)	0.0530 (7)	0.0094 (5)	0.0182 (5)	−0.0002 (6)
C15	0.0532 (8)	0.0630 (9)	0.0511 (8)	0.0150 (6)	0.0302 (6)	0.0071 (6)
C16	0.0486 (7)	0.0502 (7)	0.0464 (7)	0.0102 (6)	0.0199 (6)	0.0079 (6)

Geometric parameters (Å, º) top

O1—C10	1.2267 (15)	C6—H6	0.9300
O2—C13	1.3593 (15)	C7—H7A	0.9600
O2—H2	0.8200	C7—H7B	0.9600
N1—C4	1.3745 (17)	C7—H7C	0.9600
N1—C7	1.427 (2)	C8—H8A	0.9600
N1—C8	1.436 (2)	C8—H8B	0.9600
N2—C9	1.2757 (16)	C8—H8C	0.9600
N2—N3	1.3848 (14)	C9—H9	0.9300
N3—C10	1.3475 (17)	C10—C11	1.4958 (16)
N3—H3A	0.895 (9)	C11—C16	1.3864 (18)
C1—C6	1.3907 (17)	C11—C12	1.3878 (17)
C1—C2	1.3942 (17)	C12—C13	1.3842 (17)
C1—C9	1.4531 (17)	C12—H12	0.9300
C2—C3	1.3706 (17)	C13—C14	1.3868 (17)
C2—H2A	0.9300	C14—C15	1.3783 (19)
C3—C4	1.4025 (18)	C14—H14	0.9300
C3—H3	0.9300	C15—C16	1.3841 (18)
C4—C5	1.4025 (19)	C15—H15	0.9300
C5—C6	1.3744 (18)	C16—H16	0.9300
C5—H5	0.9300

C13—O2—H2	109.5	H7B—C7—H7C	109.5
C4—N1—C7	121.53 (13)	N1—C8—H8A	109.5
C4—N1—C8	120.99 (13)	N1—C8—H8B	109.5
C7—N1—C8	117.43 (13)	H8A—C8—H8B	109.5
C9—N2—N3	115.57 (10)	N1—C8—H8C	109.5
C10—N3—N2	118.66 (10)	H8A—C8—H8C	109.5
C10—N3—H3A	122.7 (12)	H8B—C8—H8C	109.5
N2—N3—H3A	117.2 (12)	N2—C9—C1	121.94 (11)
C6—C1—C2	116.93 (11)	N2—C9—H9	119.0
C6—C1—C9	120.27 (11)	C1—C9—H9	119.0
C2—C1—C9	122.80 (11)	O1—C10—N3	121.76 (11)
C3—C2—C1	121.39 (12)	O1—C10—C11	121.68 (12)
C3—C2—H2A	119.3	N3—C10—C11	116.56 (10)
C1—C2—H2A	119.3	C16—C11—C12	119.87 (11)
C2—C3—C4	121.75 (11)	C16—C11—C10	123.77 (11)
C2—C3—H3	119.1	C12—C11—C10	116.35 (10)
C4—C3—H3	119.1	C13—C12—C11	120.32 (10)
N1—C4—C5	122.05 (12)	C13—C12—H12	119.8
N1—C4—C3	121.11 (12)	C11—C12—H12	119.8
C5—C4—C3	116.84 (11)	O2—C13—C12	122.41 (10)
C6—C5—C4	120.73 (12)	O2—C13—C14	117.75 (11)
C6—C5—H5	119.6	C12—C13—C14	119.84 (11)
C4—C5—H5	119.6	C15—C14—C13	119.55 (11)
C5—C6—C1	122.33 (11)	C15—C14—H14	120.2
C5—C6—H6	118.8	C13—C14—H14	120.2
C1—C6—H6	118.8	C14—C15—C16	121.09 (12)
N1—C7—H7A	109.5	C14—C15—H15	119.5
N1—C7—H7B	109.5	C16—C15—H15	119.5
H7A—C7—H7B	109.5	C15—C16—C11	119.32 (12)
N1—C7—H7C	109.5	C15—C16—H16	120.3
H7A—C7—H7C	109.5	C11—C16—H16	120.3

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.82	2.18	2.8470 (14)	138
O2—H2···N2ⁱ	0.82	2.36	3.1008 (16)	150
N3—H3A···O1ⁱⁱ	0.90 (1)	2.56 (1)	3.4172 (16)	160 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₇N₃O₂
M_r	283.33
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	13.397 (3), 9.663 (2), 11.183 (2)
β (°)	101.97 (3)
V (Å³)	1416.2 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.28 × 0.27 × 0.27

Data collection
Diffractometer	Bruker SMART APEX area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.975, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	11531, 3094, 2579
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.130, 1.05
No. of reflections	3094
No. of parameters	196
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.29

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Version 5.1; Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.82	2.18	2.8470 (14)	138.1
O2—H2···N2ⁱ	0.82	2.36	3.1008 (16)	149.9
N3—H3A···O1ⁱⁱ	0.895 (9)	2.561 (11)	3.4172 (16)	160.4 (16)

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

References

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doi:10.1107/S160053680800130X

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