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Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): o471.
Published online 2008 January 18. doi:  10.1107/S160053680800130X
PMCID: PMC2960467

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

Abstract

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 [triangle]); Bahner et al. (1968 [triangle]); Butcher et al. (2005 [triangle]); Hodnett & Mooney (1970 [triangle]); Merchant & Chothia (1970 [triangle]); Pradeep (2005 [triangle]); Sigman & Jacobsen (1998 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o471-scheme1.jpg

Experimental

Crystal data

  • C16H17N3O2
  • M r = 283.33
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o471-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.130
  • S = 1.05
  • 3094 reflections
  • 196 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.21 e Å−3
  • Δρmin = −0.29 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680800130X/su2040sup1.cif

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

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

supplementary crystallographic information

Comment

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).

Experimental

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.

Refinement

H3A was located from a difference Fourier map and refined with the N–H distance restrained to 0.90 (1) Å, and Uiso(H) = 0.08 Å2. Other H atoms were positioned geometrically (C–H = 0.93–0.96Å and O–H = 0.82 Å) and treated as riding atoms, with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(O and methyl-C).

Figures

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].

Crystal data

C16H17N3O2F000 = 600
Mr = 283.33Dx = 1.329 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4593 reflections
a = 13.397 (3) Åθ = 2.5–27.7º
b = 9.663 (2) ŵ = 0.09 mm1
c = 11.183 (2) ÅT = 298 (2) K
β = 101.97 (3)ºBlock, yellow
V = 1416.2 (5) Å30.28 × 0.27 × 0.27 mm
Z = 4

Data collection

Bruker SMART APEX area-detector diffractometer3094 independent reflections
Radiation source: fine-focus sealed tube2579 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.021
T = 298(2) Kθmax = 27.0º
ω scansθmin = 2.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −16→17
Tmin = 0.975, Tmax = 0.976k = −12→12
11531 measured reflectionsl = −14→14

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.130  w = 1/[σ2(Fo2) + (0.0773P)2 + 0.1729P] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
3094 reflectionsΔρmax = 0.21 e Å3
196 parametersΔρmin = −0.29 e Å3
1 restraintExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

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)

xyzUiso*/Ueq
O10.51231 (8)0.27675 (11)0.29293 (9)0.0574 (3)
O20.28657 (7)0.69755 (10)0.22473 (9)0.0486 (3)
H20.33150.70060.18490.073*
N10.97117 (10)−0.30631 (15)0.63913 (13)0.0654 (4)
N20.60441 (8)0.13189 (10)0.48763 (10)0.0416 (3)
N30.52359 (8)0.22033 (11)0.49046 (10)0.0420 (3)
C10.72192 (9)−0.03254 (12)0.59700 (11)0.0379 (3)
C20.78863 (10)−0.03161 (13)0.51647 (11)0.0430 (3)
H2A0.77740.03020.45130.052*
C30.87041 (10)−0.11981 (14)0.53134 (12)0.0445 (3)
H30.9138−0.11570.47640.053*
C40.89036 (9)−0.21613 (13)0.62715 (12)0.0425 (3)
C50.82405 (10)−0.21577 (14)0.70911 (12)0.0456 (3)
H50.8352−0.27700.77470.055*
C60.74284 (10)−0.12595 (14)0.69358 (11)0.0424 (3)
H60.7004−0.12770.74960.051*
C70.99119 (16)−0.4061 (2)0.73523 (17)0.0793 (6)
H7A1.0129−0.35970.81210.119*
H7B1.0439−0.46790.72190.119*
H7C0.9302−0.45780.73630.119*
C81.04154 (15)−0.2992 (2)0.5584 (2)0.0903 (7)
H8A1.0063−0.31940.47640.135*
H8B1.0952−0.36550.58350.135*
H8C1.0702−0.20790.56120.135*
C90.63422 (9)0.05897 (13)0.58348 (11)0.0411 (3)
H90.59880.06450.64660.049*
C100.48449 (9)0.29458 (12)0.38962 (12)0.0397 (3)
C110.40510 (9)0.39961 (12)0.40150 (11)0.0375 (3)
C120.38258 (9)0.49733 (12)0.30887 (11)0.0375 (3)
H120.41680.49540.24460.045*
C130.30939 (9)0.59770 (12)0.31174 (11)0.0380 (3)
C140.25681 (10)0.59887 (14)0.40629 (12)0.0453 (3)
H140.20670.66510.40800.054*
C150.27927 (11)0.50121 (16)0.49776 (13)0.0530 (4)
H150.24400.50210.56110.064*
C160.35350 (10)0.40181 (14)0.49689 (12)0.0469 (3)
H160.36860.33720.55960.056*
H3A0.5095 (14)0.2388 (19)0.5637 (11)0.080*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0646 (6)0.0592 (6)0.0572 (6)0.0197 (5)0.0327 (5)0.0044 (5)
O20.0480 (5)0.0487 (5)0.0530 (6)0.0081 (4)0.0192 (4)0.0094 (4)
N10.0552 (7)0.0751 (9)0.0698 (8)0.0289 (7)0.0219 (6)0.0220 (7)
N20.0369 (5)0.0388 (6)0.0501 (6)0.0050 (4)0.0114 (4)−0.0082 (4)
N30.0380 (5)0.0417 (6)0.0485 (6)0.0072 (4)0.0137 (5)−0.0065 (5)
C10.0368 (6)0.0382 (6)0.0391 (6)−0.0001 (5)0.0087 (5)−0.0057 (5)
C20.0452 (7)0.0451 (7)0.0400 (6)0.0056 (5)0.0115 (5)0.0069 (5)
C30.0427 (7)0.0535 (8)0.0407 (7)0.0056 (5)0.0162 (5)0.0024 (5)
C40.0388 (6)0.0447 (7)0.0432 (7)0.0046 (5)0.0067 (5)0.0001 (5)
C50.0467 (7)0.0504 (7)0.0397 (7)0.0023 (6)0.0085 (5)0.0086 (5)
C60.0428 (7)0.0499 (7)0.0373 (6)−0.0026 (5)0.0149 (5)−0.0027 (5)
C70.0834 (12)0.0834 (13)0.0713 (11)0.0421 (10)0.0162 (9)0.0196 (9)
C80.0656 (11)0.1028 (15)0.1139 (16)0.0410 (11)0.0449 (11)0.0305 (13)
C90.0394 (6)0.0403 (6)0.0456 (7)0.0004 (5)0.0131 (5)−0.0074 (5)
C100.0359 (6)0.0369 (6)0.0497 (7)0.0000 (5)0.0165 (5)−0.0046 (5)
C110.0332 (6)0.0371 (6)0.0442 (7)−0.0012 (5)0.0122 (5)−0.0055 (5)
C120.0352 (6)0.0394 (6)0.0412 (6)−0.0024 (5)0.0156 (5)−0.0044 (5)
C130.0345 (6)0.0378 (6)0.0423 (6)−0.0024 (5)0.0095 (5)−0.0018 (5)
C140.0393 (6)0.0472 (7)0.0530 (7)0.0094 (5)0.0182 (5)−0.0002 (6)
C150.0532 (8)0.0630 (9)0.0511 (8)0.0150 (6)0.0302 (6)0.0071 (6)
C160.0486 (7)0.0502 (7)0.0464 (7)0.0102 (6)0.0199 (6)0.0079 (6)

Geometric parameters (Å, °)

O1—C101.2267 (15)C6—H60.9300
O2—C131.3593 (15)C7—H7A0.9600
O2—H20.8200C7—H7B0.9600
N1—C41.3745 (17)C7—H7C0.9600
N1—C71.427 (2)C8—H8A0.9600
N1—C81.436 (2)C8—H8B0.9600
N2—C91.2757 (16)C8—H8C0.9600
N2—N31.3848 (14)C9—H90.9300
N3—C101.3475 (17)C10—C111.4958 (16)
N3—H3A0.895 (9)C11—C161.3864 (18)
C1—C61.3907 (17)C11—C121.3878 (17)
C1—C21.3942 (17)C12—C131.3842 (17)
C1—C91.4531 (17)C12—H120.9300
C2—C31.3706 (17)C13—C141.3868 (17)
C2—H2A0.9300C14—C151.3783 (19)
C3—C41.4025 (18)C14—H140.9300
C3—H30.9300C15—C161.3841 (18)
C4—C51.4025 (19)C15—H150.9300
C5—C61.3744 (18)C16—H160.9300
C5—H50.9300
C13—O2—H2109.5H7B—C7—H7C109.5
C4—N1—C7121.53 (13)N1—C8—H8A109.5
C4—N1—C8120.99 (13)N1—C8—H8B109.5
C7—N1—C8117.43 (13)H8A—C8—H8B109.5
C9—N2—N3115.57 (10)N1—C8—H8C109.5
C10—N3—N2118.66 (10)H8A—C8—H8C109.5
C10—N3—H3A122.7 (12)H8B—C8—H8C109.5
N2—N3—H3A117.2 (12)N2—C9—C1121.94 (11)
C6—C1—C2116.93 (11)N2—C9—H9119.0
C6—C1—C9120.27 (11)C1—C9—H9119.0
C2—C1—C9122.80 (11)O1—C10—N3121.76 (11)
C3—C2—C1121.39 (12)O1—C10—C11121.68 (12)
C3—C2—H2A119.3N3—C10—C11116.56 (10)
C1—C2—H2A119.3C16—C11—C12119.87 (11)
C2—C3—C4121.75 (11)C16—C11—C10123.77 (11)
C2—C3—H3119.1C12—C11—C10116.35 (10)
C4—C3—H3119.1C13—C12—C11120.32 (10)
N1—C4—C5122.05 (12)C13—C12—H12119.8
N1—C4—C3121.11 (12)C11—C12—H12119.8
C5—C4—C3116.84 (11)O2—C13—C12122.41 (10)
C6—C5—C4120.73 (12)O2—C13—C14117.75 (11)
C6—C5—H5119.6C12—C13—C14119.84 (11)
C4—C5—H5119.6C15—C14—C13119.55 (11)
C5—C6—C1122.33 (11)C15—C14—H14120.2
C5—C6—H6118.8C13—C14—H14120.2
C1—C6—H6118.8C14—C15—C16121.09 (12)
N1—C7—H7A109.5C14—C15—H15119.5
N1—C7—H7B109.5C16—C15—H15119.5
H7A—C7—H7B109.5C15—C16—C11119.32 (12)
N1—C7—H7C109.5C15—C16—H16120.3
H7A—C7—H7C109.5C11—C16—H16120.3

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H2···O1i0.822.182.8470 (14)138
O2—H2···N2i0.822.363.1008 (16)150
N3—H3A···O1ii0.895 (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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2040).

References

  • Akitsu, T. & Einaga, Y. (2006). Acta Cryst. E62, o4315–o4317.
  • Bahner, C. T., Brotherton, D. & Brotherton, M. K. (1968). J. Med. Chem.11, 405–406. [PubMed]
  • Butcher, R. J., Basu Baul, T. S., Singh, K. S. & Smith, F. E. (2005). Acta Cryst. E61, o1007–o1009.
  • Hodnett, E. M. & Mooney, P. D. (1970). J. Med. Chem.13, 786. [PubMed]
  • Merchant, J. R. & Chothia, D. S. (1970). J. Med. Chem.13, 335–336. [PubMed]
  • Pradeep, C. P. (2005). Acta Cryst. E61, o3825–o3827.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
  • Sigman, M. S. & Jacobsen, E. N. (1998). J. Am. Chem. Soc.120, 4901–4902.

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