organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

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[Akitsu, T. & Einaga, Y. (2006). Acta Cryst. E62, o4315-o4317.]); Bahner et al. (1968[Bahner, C. T., Brotherton, D. & Brotherton, M. K. (1968). J. Med. Chem. 11, 405-406.]); Butcher et al. (2005[Butcher, R. J., Basu Baul, T. S., Singh, K. S. & Smith, F. E. (2005). Acta Cryst. E61, o1007-o1009.]); Hodnett & Mooney (1970[Hodnett, E. M. & Mooney, P. D. (1970). J. Med. Chem. 13, 786.]); Merchant & Chothia (1970[Merchant, J. R. & Chothia, D. S. (1970). J. Med. Chem. 13, 335-336.]); Pradeep (2005[Pradeep, C. P. (2005). Acta Cryst. E61, o3825-o3827.]); Sigman & Jacobsen (1998[Sigman, M. S. & Jacobsen, E. N. (1998). J. Am. Chem. Soc. 120, 4901-4902.]).

[Scheme 1]

Experimental

Crystal data
  • C16H17N3O2

  • Mr = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.975, Tmax = 0.976

  • 11531 measured reflections

  • 3094 independent reflections

  • 2579 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.29 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


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.

Refinement top

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).

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
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atom labelling scheme and displacement ellipsoids drawn at the 30% probability level.
[Figure 2] 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
C16H17N3O2F(000) = 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 = 2.5–27.7°
b = 9.663 (2) ŵ = 0.09 mm1
c = 11.183 (2) ÅT = 298 K
β = 101.97 (3)°Block, yellow
V = 1416.2 (5) Å30.28 × 0.27 × 0.27 mm
Z = 4
Data collection top
Bruker SMART APEX area-detector
diffractometer
3094 independent reflections
Radiation source: fine-focus sealed tube2579 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
ω scansθmax = 27.0°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1617
Tmin = 0.975, Tmax = 0.976k = 1212
11531 measured reflectionsl = 1414
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0773P)2 + 0.1729P]
where P = (Fo2 + 2Fc2)/3
3094 reflections(Δ/σ)max < 0.001
196 parametersΔρmax = 0.21 e Å3
1 restraintΔρmin = 0.29 e Å3
Crystal data top
C16H17N3O2V = 1416.2 (5) Å3
Mr = 283.33Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.397 (3) ŵ = 0.09 mm1
b = 9.663 (2) ÅT = 298 K
c = 11.183 (2) Å0.28 × 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)
Tmin = 0.975, Tmax = 0.976Rint = 0.021
11531 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0441 restraint
wR(F2) = 0.130H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.21 e Å3
3094 reflectionsΔρmin = 0.29 e Å3
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
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)
H30.91380.11570.47640.053*
C40.89036 (9)0.21613 (13)0.62715 (12)0.0425 (3)
C50.82405 (10)0.21577 (14)0.70911 (12)0.0456 (3)
H50.83520.27700.77470.055*
C60.74284 (10)0.12595 (14)0.69358 (11)0.0424 (3)
H60.70040.12770.74960.051*
C70.99119 (16)0.4061 (2)0.73523 (17)0.0793 (6)
H7A1.01290.35970.81210.119*
H7B1.04390.46790.72190.119*
H7C0.93020.45780.73630.119*
C81.04154 (15)0.2992 (2)0.5584 (2)0.0903 (7)
H8A1.00630.31940.47640.135*
H8B1.09520.36550.58350.135*
H8C1.07020.20790.56120.135*
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) top
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, º) top
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, º) top
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···O1ii0.90 (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 formulaC16H17N3O2
Mr283.33
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)13.397 (3), 9.663 (2), 11.183 (2)
β (°) 101.97 (3)
V3)1416.2 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.28 × 0.27 × 0.27
Data collection
DiffractometerBruker SMART APEX area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.975, 0.976
No. of measured, independent and
observed [I > 2σ(I)] reflections
11531, 3094, 2579
Rint0.021
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.130, 1.05
No. of reflections3094
No. of parameters196
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
O2—H2···O1i0.822.182.8470 (14)138.1
O2—H2···N2i0.822.363.1008 (16)149.9
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.
 

References

First citationAkitsu, T. & Einaga, Y. (2006). Acta Cryst. E62, o4315–o4317.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationBahner, C. T., Brotherton, D. & Brotherton, M. K. (1968). J. Med. Chem. 11, 405–406.  CrossRef CAS PubMed Web of Science Google Scholar
First citationButcher, R. J., Basu Baul, T. S., Singh, K. S. & Smith, F. E. (2005). Acta Cryst. E61, o1007–o1009.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationHodnett, E. M. & Mooney, P. D. (1970). J. Med. Chem. 13, 786.  CrossRef PubMed Web of Science Google Scholar
First citationMerchant, J. R. & Chothia, D. S. (1970). J. Med. Chem. 13, 335–336.  CrossRef CAS PubMed Web of Science Google Scholar
First citationPradeep, C. P. (2005). Acta Cryst. E61, o3825–o3827.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSiemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.  Google Scholar
First citationSigman, M. S. & Jacobsen, E. N. (1998). J. Am. Chem. Soc. 120, 4901–4902.  Web of Science CrossRef CAS Google Scholar

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