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

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4-Hy­dr­oxy-N′-(4-hy­dr­oxy-3-nitro­benzyl­­idene)benzohydrazide

aExperimental Center, Linyi University, Linyi Shandong 276005, People's Republic of China
*Correspondence e-mail: zhangzhen_lynu@126.com

(Received 28 December 2010; accepted 4 January 2011; online 8 January 2011)

The mol­ecule of the title compound, C14H11N3O5, assumes an E configuration with respect to the methyl­idene unit. An intra­molecular O—H⋯O hydrogen bond is present in the mol­ecule. The dihedral angle between the mean planes of the two benzene rings is 5.46 (15)°. The crystal structure is stabilized by inter­molecular O—H⋯O, O—H⋯N, and N—H⋯O hydrogen bonds.

Related literature

For the biological applications of hydrazone compounds, see: Ajani et al. (2010[Ajani, O. O., Obafemi, C. A., Nwinyi, O. C. & Akinpelu, D. A. (2010). Bioorg. Med. Chem. 18, 214-221.]); Avaji et al. (2009[Avaji, P. G., Kumar, C. H. V., Patil, S. A., Shivananda, K. N. & Nagaraju, C. (2009). Eur. J. Med. Chem. 44, 3552-3559.]); Fan et al. (2010[Fan, C. D., Su, H., Zhao, J., Zhao, B. X., Zhang, S. L. & Miao, J. Y. (2010). Eur. J. Med. Chem. 45, 1438-1446.]); Rasras et al. (2010[Rasras, A. J. M., Al-Tel, T. H., Amal, A. F. & Al-Qawasmeh, R. A. (2010). Eur. J. Med. Chem. 45, 2307-2313.]). For similar hydrazone compounds, see: Ahmad et al. (2010[Ahmad, T., Zia-ur-Rehman, M., Siddiqui, H. L., Mahmud, S. & Parvez, M. (2010). Acta Cryst. E66, o976.]); Ban (2010[Ban, H.-Y. (2010). Acta Cryst. E66, o3240.]); Ji & Lu (2010[Ji, X.-H. & Lu, J.-F. (2010). Acta Cryst. E66, o1514.]); Shalash et al. (2010[Shalash, M., Salhin, A., Adnan, R., Yeap, C. S. & Fun, H.-K. (2010). Acta Cryst. E66, o3126-o3127.]).

[Scheme 1]

Experimental

Crystal data
  • C14H11N3O5

  • Mr = 301.26

  • Monoclinic, P 21 /n

  • a = 8.786 (3) Å

  • b = 14.882 (2) Å

  • c = 10.3064 (17) Å

  • β = 91.100 (2)°

  • V = 1347.3 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.12 mm−1

  • T = 298 K

  • 0.32 × 0.30 × 0.29 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.964, Tmax = 0.967

  • 7079 measured reflections

  • 2952 independent reflections

  • 1353 reflections with I > 2σ(I)

  • Rint = 0.050

Refinement
  • R[F2 > 2σ(F2)] = 0.054

  • wR(F2) = 0.137

  • S = 1.06

  • 2952 reflections

  • 204 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1A⋯O2i 0.82 1.93 2.736 (3) 169
O1—H1A⋯N2i 0.82 2.61 3.121 (3) 122
O3—H3⋯O4 0.82 1.90 2.592 (4) 142
N1—H1⋯O5ii 0.90 (1) 2.32 (1) 3.203 (4) 167 (3)
Symmetry codes: (i) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) -x, -y+1, -z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS 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: SHELXTL.

Supporting information


Comment top

Hydrazone compounds have received much attention due to their potential applications in biological chemistry (Ajani et al., 2010; Avaji et al., 2009; Fan et al., 2010; Rasras et al., 2010). As a continuatio of our work on the hydrazone compounds, the new title hydrazone compound was prepared and structurally characterized.

The molecule of the title compound assumes an E configuration with respect to the methylidene unit (Fig. 1). The dihedral angle between the best mean planes of the two benzene rings is 5.46 (15)°. An intramolecular O—H···O hydrogen bond is present in the molecule (Table 1). The bond lengths are comparable to those observed in similar hydrazone compounds (Ahmad et al., 2010; Ban, 2010; Ji & Lu, 2010; Shalash et al., 2010).

The crystal structure is stabilized by intermolecular O—H···O, O—H···N, and N—H···O hydrogen bonds (Table 1 and Fig. 2).

Related literature top

For the biological applications of hydrazone compounds, see: Ajani et al. (2010); Avaji et al. (2009); Fan et al. (2010); Rasras et al. (2010). For similar hydrazone compounds, see: Ahmad et al. (2010); Ban (2010); Ji & Lu (2010); Shalash et al. (2010).

Experimental top

An ethanol solution (50 ml) of 4-hydroxybenzohydrazide (0.01 mol) and 4-hydroxy-3-nitrobenzaldehyde (0.01 mol) was stirred at room temperature for 30 min to give a yellow solution. Yellow block-shaped single crystals, suitable for X-ray diffraction, were formed by slow evaporation of the solution in air.

Refinement top

The amino H-atom, H1, was located from a difference Fourier map and refined with a N—H distance restraint to 0.90 (1) Å. The remaining H atoms were positioned geometrically and refined using the riding-model approximation: C—H = 0.93 Å, and O—H = 0.82 Å, with Uiso(H) = 1.2Ueq(parent C-atom) and 1.5Ueq(parent O-atom).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of the title compound, showing the displacement ellipsoids at the 30% probability level. The intramolecular O—H···O hydrogen bond is shown as a dashed line.
[Figure 2] Fig. 2. A perspective view along the a-axis of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines. H-atoms not involved in hydrogen bonding have been omitted for clarity.
4-Hydroxy-N'-(4-hydroxy-3-nitrobenzylidene)benzohydrazide top
Crystal data top
C14H11N3O5F(000) = 624
Mr = 301.26Dx = 1.485 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 8.786 (3) ÅCell parameters from 1674 reflections
b = 14.882 (2) Åθ = 2.4–26.9°
c = 10.3064 (17) ŵ = 0.12 mm1
β = 91.100 (2)°T = 298 K
V = 1347.3 (5) Å3Block, yellow
Z = 40.32 × 0.30 × 0.29 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2952 independent reflections
Radiation source: fine-focus sealed tube1353 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
ω scansθmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
h = 911
Tmin = 0.964, Tmax = 0.967k = 1919
7079 measured reflectionsl = 137
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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.0262P)2 + 0.9404P]
where P = (Fo2 + 2Fc2)/3
2952 reflections(Δ/σ)max < 0.001
204 parametersΔρmax = 0.21 e Å3
1 restraintΔρmin = 0.21 e Å3
Crystal data top
C14H11N3O5V = 1347.3 (5) Å3
Mr = 301.26Z = 4
Monoclinic, P21/nMo Kα radiation
a = 8.786 (3) ŵ = 0.12 mm1
b = 14.882 (2) ÅT = 298 K
c = 10.3064 (17) Å0.32 × 0.30 × 0.29 mm
β = 91.100 (2)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2952 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
1353 reflections with I > 2σ(I)
Tmin = 0.964, Tmax = 0.967Rint = 0.050
7079 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0541 restraint
wR(F2) = 0.137H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.21 e Å3
2952 reflectionsΔρmin = 0.21 e Å3
204 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
N10.4602 (3)0.40859 (16)0.1386 (3)0.0442 (7)
N20.3606 (3)0.34194 (16)0.0989 (3)0.0419 (7)
O11.0054 (2)0.64891 (13)0.3680 (3)0.0577 (7)
H1A0.97040.69980.36140.087*
O20.6482 (2)0.30744 (13)0.1654 (2)0.0521 (7)
O30.2256 (3)0.12672 (15)0.0998 (3)0.0675 (8)
H30.30470.15290.12000.101*
O40.3830 (3)0.26935 (19)0.1553 (3)0.0766 (9)
O50.2875 (3)0.40196 (19)0.1256 (3)0.0801 (9)
C10.7049 (3)0.45812 (18)0.2226 (3)0.0344 (7)
C20.6644 (3)0.54841 (18)0.2232 (3)0.0411 (8)
H20.56910.56550.19090.049*
C30.7623 (3)0.61274 (19)0.2707 (3)0.0432 (8)
H3A0.73320.67280.26990.052*
C40.9033 (3)0.58892 (19)0.3194 (3)0.0398 (8)
C50.9456 (4)0.49917 (19)0.3202 (3)0.0503 (10)
H51.04060.48240.35340.060*
C60.8471 (3)0.4349 (2)0.2720 (3)0.0503 (10)
H60.87660.37490.27260.060*
C70.6036 (3)0.38575 (19)0.1743 (3)0.0382 (8)
C80.2280 (4)0.3678 (2)0.0654 (3)0.0444 (9)
H80.20470.42870.06850.053*
C90.1110 (3)0.3044 (2)0.0222 (3)0.0398 (8)
C100.0244 (3)0.3372 (2)0.0261 (3)0.0428 (8)
H100.03980.39890.03010.051*
C110.1385 (3)0.2798 (2)0.0692 (3)0.0410 (8)
C120.1193 (4)0.1874 (2)0.0631 (3)0.0455 (9)
C130.0193 (4)0.1544 (2)0.0147 (3)0.0486 (9)
H130.03470.09260.01020.058*
C140.1324 (4)0.2110 (2)0.0262 (3)0.0446 (9)
H140.22430.18750.05690.053*
N30.2779 (3)0.3202 (2)0.1195 (3)0.0561 (8)
H10.424 (3)0.4649 (10)0.144 (3)0.067*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0310 (16)0.0268 (13)0.075 (2)0.0000 (12)0.0032 (14)0.0041 (14)
N20.0364 (17)0.0336 (14)0.0558 (19)0.0036 (12)0.0034 (14)0.0015 (13)
O10.0463 (15)0.0301 (12)0.0962 (19)0.0006 (11)0.0149 (14)0.0028 (13)
O20.0450 (14)0.0267 (11)0.0845 (18)0.0024 (10)0.0015 (12)0.0041 (12)
O30.0593 (17)0.0626 (16)0.081 (2)0.0226 (13)0.0018 (15)0.0094 (15)
O40.0474 (17)0.094 (2)0.088 (2)0.0095 (16)0.0138 (15)0.0119 (17)
O50.0598 (18)0.0628 (18)0.117 (2)0.0151 (15)0.0165 (16)0.0017 (17)
C10.0307 (18)0.0281 (15)0.045 (2)0.0001 (13)0.0075 (15)0.0008 (14)
C20.033 (2)0.0310 (17)0.060 (2)0.0037 (14)0.0008 (17)0.0031 (15)
C30.040 (2)0.0259 (16)0.064 (2)0.0021 (14)0.0000 (17)0.0058 (16)
C40.0373 (19)0.0296 (16)0.052 (2)0.0024 (14)0.0029 (17)0.0002 (15)
C50.036 (2)0.0318 (17)0.082 (3)0.0063 (16)0.0109 (19)0.0018 (18)
C60.043 (2)0.0273 (17)0.080 (3)0.0083 (15)0.004 (2)0.0029 (17)
C70.037 (2)0.0315 (17)0.046 (2)0.0021 (14)0.0081 (16)0.0033 (15)
C80.041 (2)0.0315 (17)0.061 (2)0.0032 (15)0.0027 (18)0.0009 (16)
C90.0335 (19)0.0374 (17)0.049 (2)0.0010 (14)0.0075 (16)0.0014 (16)
C100.037 (2)0.0374 (18)0.054 (2)0.0014 (15)0.0057 (17)0.0008 (16)
C110.034 (2)0.048 (2)0.042 (2)0.0007 (15)0.0065 (16)0.0042 (16)
C120.044 (2)0.050 (2)0.042 (2)0.0134 (17)0.0061 (17)0.0068 (17)
C130.055 (2)0.0335 (17)0.057 (2)0.0027 (17)0.0083 (19)0.0020 (17)
C140.041 (2)0.0375 (19)0.056 (2)0.0010 (15)0.0033 (17)0.0012 (16)
N30.0403 (19)0.071 (2)0.057 (2)0.0008 (17)0.0035 (16)0.0043 (17)
Geometric parameters (Å, º) top
N1—C71.349 (4)C3—H3A0.9300
N1—N21.380 (3)C4—C51.387 (4)
N1—H10.899 (10)C5—C61.376 (4)
N2—C81.269 (4)C5—H50.9300
O1—C41.355 (3)C6—H60.9300
O1—H1A0.8200C8—C91.458 (4)
O2—C71.234 (3)C8—H80.9300
O3—C121.347 (4)C9—C101.371 (4)
O3—H30.8200C9—C141.403 (4)
O4—N31.244 (3)C10—C111.383 (4)
O5—N31.222 (4)C10—H100.9300
C1—C61.383 (4)C11—C121.387 (4)
C1—C21.390 (4)C11—N31.451 (4)
C1—C71.478 (4)C12—C131.396 (4)
C2—C31.371 (4)C13—C141.363 (4)
C2—H20.9300C13—H130.9300
C3—C41.374 (4)C14—H140.9300
C7—N1—N2118.9 (2)N1—C7—C1117.5 (3)
C7—N1—H1123 (2)N2—C8—C9121.7 (3)
N2—N1—H1118 (2)N2—C8—H8119.2
C8—N2—N1115.9 (2)C9—C8—H8119.2
C4—O1—H1A109.5C10—C9—C14118.5 (3)
C12—O3—H3109.5C10—C9—C8118.9 (3)
C6—C1—C2118.0 (3)C14—C9—C8122.6 (3)
C6—C1—C7118.4 (3)C9—C10—C11121.0 (3)
C2—C1—C7123.6 (3)C9—C10—H10119.5
C3—C2—C1121.1 (3)C11—C10—H10119.5
C3—C2—H2119.4C10—C11—C12120.8 (3)
C1—C2—H2119.4C10—C11—N3117.4 (3)
C2—C3—C4120.4 (3)C12—C11—N3121.9 (3)
C2—C3—H3A119.8O3—C12—C11124.7 (3)
C4—C3—H3A119.8O3—C12—C13117.3 (3)
O1—C4—C3123.4 (3)C11—C12—C13118.0 (3)
O1—C4—C5117.2 (3)C14—C13—C12121.2 (3)
C3—C4—C5119.4 (3)C14—C13—H13119.4
C6—C5—C4120.0 (3)C12—C13—H13119.4
C6—C5—H5120.0C13—C14—C9120.5 (3)
C4—C5—H5120.0C13—C14—H14119.8
C5—C6—C1121.1 (3)C9—C14—H14119.8
C5—C6—H6119.4O5—N3—O4122.7 (3)
C1—C6—H6119.4O5—N3—C11119.2 (3)
O2—C7—N1120.9 (3)O4—N3—C11118.1 (3)
O2—C7—C1121.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O2i0.821.932.736 (3)169
O1—H1A···N2i0.822.613.121 (3)122
O3—H3···O40.821.902.592 (4)142
N1—H1···O5ii0.90 (1)2.32 (1)3.203 (4)167 (3)
Symmetry codes: (i) x+3/2, y+1/2, z+1/2; (ii) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC14H11N3O5
Mr301.26
Crystal system, space groupMonoclinic, P21/n
Temperature (K)298
a, b, c (Å)8.786 (3), 14.882 (2), 10.3064 (17)
β (°) 91.100 (2)
V3)1347.3 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.12
Crystal size (mm)0.32 × 0.30 × 0.29
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.964, 0.967
No. of measured, independent and
observed [I > 2σ(I)] reflections
7079, 2952, 1353
Rint0.050
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.054, 0.137, 1.06
No. of reflections2952
No. of parameters204
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.21, 0.21

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O2i0.821.932.736 (3)169
O1—H1A···N2i0.822.613.121 (3)122
O3—H3···O40.821.902.592 (4)142
N1—H1···O5ii0.899 (10)2.321 (13)3.203 (4)167 (3)
Symmetry codes: (i) x+3/2, y+1/2, z+1/2; (ii) x, y+1, z.
 

Acknowledgements

The author thanks the Experimental Center of Linyi University for supporting this work.

References

First citationAhmad, T., Zia-ur-Rehman, M., Siddiqui, H. L., Mahmud, S. & Parvez, M. (2010). Acta Cryst. E66, o976.  Web of Science CrossRef IUCr Journals Google Scholar
First citationAjani, O. O., Obafemi, C. A., Nwinyi, O. C. & Akinpelu, D. A. (2010). Bioorg. Med. Chem. 18, 214–221.  Web of Science CrossRef PubMed CAS Google Scholar
First citationAvaji, P. G., Kumar, C. H. V., Patil, S. A., Shivananda, K. N. & Nagaraju, C. (2009). Eur. J. Med. Chem. 44, 3552–3559.  Web of Science CrossRef PubMed CAS Google Scholar
First citationBan, H.-Y. (2010). Acta Cryst. E66, o3240.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationBruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFan, C. D., Su, H., Zhao, J., Zhao, B. X., Zhang, S. L. & Miao, J. Y. (2010). Eur. J. Med. Chem. 45, 1438–1446.  Web of Science CrossRef CAS PubMed Google Scholar
First citationJi, X.-H. & Lu, J.-F. (2010). Acta Cryst. E66, o1514.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationRasras, A. J. M., Al-Tel, T. H., Amal, A. F. & Al-Qawasmeh, R. A. (2010). Eur. J. Med. Chem. 45, 2307–2313.  Web of Science CrossRef CAS PubMed Google Scholar
First citationShalash, M., Salhin, A., Adnan, R., Yeap, C. S. & Fun, H.-K. (2010). Acta Cryst. E66, o3126–o3127.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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