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organic compounds
(E)-4-Chloro-N′-(4-hydroxybenzylidene)benzohydrazide
aDepartment of Chemistry and Chemical Engineering, Baoji University of Arts and Sciences, Baoji 721007, People's Republic of China
*Correspondence e-mail: desuoyang@yahoo.com.cn
The molecule of the title compound, C14H11ClN2O2, displays a trans configuration with respect to the C=N double bond. The dihedral angle between the two benzene rings is 12.8 (3)°. In the molecules are linked through intermolecular O—H⋯O and N—H⋯O hydrogen bonds and C—H⋯π interactions, forming a three-dimensional network.
Related literature
For related structures, see: Yang (2007, 2008a
,b
). For bond-length data, see: Allen et al. (1987
). For related literature, see: Bernardo et al. (1996
); Musie et al. (2001
); Paul et al. (2002
).
Experimental
Crystal data
|
Refinement
|
|
Data collection: SMART (Bruker, 2002); cell 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
10.1107/S1600536808027013/ci2657sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808027013/ci2657Isup2.hkl
4-Hydroxybenzaldehyde (0.1 mmol, 12.2 mg) and 4-chlorobenzohydrazide (0.1 mmol, 17.0 mg) were dissolved in MeOH (10 ml). The mixture was stirred at room temperature to give a clear colourless solution. Crystals of the title compound were formed by gradual evaporation of the solvent over a period of 5 days at room temperature.
Atom H2A was located in a difference Fourier map and refined isotropically, with N—H distance restrained to 0.90 (1) Å and with a Uiso of 0.08 Å2. Other H atoms were placed in idealized positions and constrained to ride on their parent atoms, with O—H distance of 0.82 Å, C—H distances of 0.93 Å, and with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(O).
Data collection: SMART (Bruker, 2002); cell
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).C14H11ClN2O2 | F(000) = 1136 |
Mr = 274.70 | Dx = 1.443 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 1916 reflections |
a = 26.251 (3) Å | θ = 2.3–24.5° |
b = 12.376 (3) Å | µ = 0.30 mm−1 |
c = 7.786 (2) Å | T = 298 K |
V = 2529.5 (9) Å3 | Block, colourless |
Z = 8 | 0.13 × 0.12 × 0.10 mm |
Bruker SMART CCD area-detector diffractometer | 2164 independent reflections |
Radiation source: fine-focus sealed tube | 1462 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.078 |
ω scans | θmax = 24.9°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −30→31 |
Tmin = 0.963, Tmax = 0.971 | k = −14→11 |
11323 measured reflections | l = −8→9 |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.116 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0433P)2 + 1.3235P] where P = (Fo2 + 2Fc2)/3 |
2164 reflections | (Δ/σ)max = 0.001 |
176 parameters | Δρmax = 0.27 e Å−3 |
1 restraint | Δρmin = −0.36 e Å−3 |
C14H11ClN2O2 | V = 2529.5 (9) Å3 |
Mr = 274.70 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 26.251 (3) Å | µ = 0.30 mm−1 |
b = 12.376 (3) Å | T = 298 K |
c = 7.786 (2) Å | 0.13 × 0.12 × 0.10 mm |
Bruker SMART CCD area-detector diffractometer | 2164 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1462 reflections with I > 2σ(I) |
Tmin = 0.963, Tmax = 0.971 | Rint = 0.078 |
11323 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 1 restraint |
wR(F2) = 0.116 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.27 e Å−3 |
2164 reflections | Δρmin = −0.36 e Å−3 |
176 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | −0.11993 (3) | 0.56136 (8) | −0.02967 (12) | 0.0721 (3) | |
N1 | 0.15097 (8) | 0.76262 (18) | 0.3530 (3) | 0.0421 (6) | |
N2 | 0.10461 (9) | 0.74598 (18) | 0.2709 (3) | 0.0401 (6) | |
O1 | 0.37436 (7) | 0.92023 (16) | 0.5358 (3) | 0.0554 (6) | |
H1 | 0.3853 | 0.9786 | 0.5022 | 0.083* | |
O2 | 0.08473 (7) | 0.61751 (14) | 0.4644 (2) | 0.0412 (5) | |
C1 | 0.22762 (10) | 0.8643 (2) | 0.3633 (3) | 0.0378 (7) | |
C2 | 0.25323 (10) | 0.7913 (2) | 0.4685 (4) | 0.0450 (7) | |
H2 | 0.2372 | 0.7273 | 0.5004 | 0.054* | |
C3 | 0.30150 (10) | 0.8119 (2) | 0.5258 (4) | 0.0463 (8) | |
H3 | 0.3178 | 0.7630 | 0.5979 | 0.056* | |
C4 | 0.32601 (10) | 0.9058 (2) | 0.4761 (3) | 0.0394 (7) | |
C5 | 0.30142 (10) | 0.9795 (2) | 0.3730 (4) | 0.0427 (7) | |
H5 | 0.3176 | 1.0435 | 0.3418 | 0.051* | |
C6 | 0.25282 (10) | 0.9580 (2) | 0.3163 (4) | 0.0440 (7) | |
H6 | 0.2366 | 1.0075 | 0.2449 | 0.053* | |
C7 | 0.17709 (10) | 0.8413 (2) | 0.2970 (4) | 0.0430 (7) | |
H7 | 0.1636 | 0.8853 | 0.2116 | 0.052* | |
C8 | 0.07391 (10) | 0.6686 (2) | 0.3321 (3) | 0.0351 (6) | |
C9 | 0.02586 (9) | 0.6472 (2) | 0.2385 (3) | 0.0335 (6) | |
C10 | −0.00001 (10) | 0.7240 (2) | 0.1430 (4) | 0.0409 (7) | |
H10 | 0.0134 | 0.7933 | 0.1331 | 0.049* | |
C11 | −0.04545 (10) | 0.6992 (2) | 0.0619 (4) | 0.0441 (7) | |
H11 | −0.0628 | 0.7512 | −0.0013 | 0.053* | |
C12 | −0.06436 (10) | 0.5965 (2) | 0.0767 (3) | 0.0435 (7) | |
C13 | −0.03996 (10) | 0.5193 (2) | 0.1731 (4) | 0.0476 (8) | |
H13 | −0.0536 | 0.4502 | 0.1827 | 0.057* | |
C14 | 0.00479 (10) | 0.5449 (2) | 0.2554 (3) | 0.0425 (7) | |
H14 | 0.0210 | 0.4934 | 0.3229 | 0.051* | |
H2A | 0.1010 (12) | 0.783 (2) | 0.172 (2) | 0.080* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0490 (5) | 0.0779 (6) | 0.0895 (7) | −0.0117 (4) | −0.0259 (5) | 0.0004 (5) |
N1 | 0.0359 (13) | 0.0460 (15) | 0.0443 (14) | −0.0041 (11) | −0.0089 (11) | 0.0015 (12) |
N2 | 0.0355 (13) | 0.0423 (14) | 0.0424 (13) | −0.0048 (11) | −0.0094 (11) | 0.0047 (11) |
O1 | 0.0404 (13) | 0.0531 (14) | 0.0726 (15) | −0.0084 (9) | −0.0133 (11) | 0.0061 (12) |
O2 | 0.0436 (11) | 0.0403 (11) | 0.0398 (10) | 0.0025 (9) | −0.0063 (9) | 0.0053 (9) |
C1 | 0.0356 (16) | 0.0400 (16) | 0.0379 (15) | −0.0022 (13) | −0.0013 (13) | −0.0006 (13) |
C2 | 0.0419 (17) | 0.0391 (16) | 0.0539 (18) | −0.0091 (13) | −0.0022 (15) | 0.0060 (14) |
C3 | 0.0428 (18) | 0.0409 (17) | 0.0552 (19) | −0.0001 (13) | −0.0092 (15) | 0.0096 (15) |
C4 | 0.0321 (16) | 0.0425 (17) | 0.0437 (16) | −0.0009 (12) | −0.0019 (13) | −0.0058 (14) |
C5 | 0.0437 (17) | 0.0371 (16) | 0.0472 (17) | −0.0063 (13) | 0.0020 (14) | 0.0023 (14) |
C6 | 0.0423 (17) | 0.0450 (18) | 0.0447 (17) | −0.0012 (14) | −0.0075 (14) | 0.0094 (13) |
C7 | 0.0400 (17) | 0.0448 (18) | 0.0442 (17) | −0.0007 (14) | −0.0071 (13) | 0.0045 (14) |
C8 | 0.0365 (16) | 0.0323 (15) | 0.0365 (15) | 0.0047 (13) | −0.0008 (12) | −0.0052 (13) |
C9 | 0.0318 (15) | 0.0361 (16) | 0.0325 (14) | 0.0037 (12) | 0.0025 (12) | 0.0007 (12) |
C10 | 0.0392 (16) | 0.0353 (16) | 0.0480 (16) | −0.0046 (13) | −0.0025 (14) | 0.0027 (13) |
C11 | 0.0391 (16) | 0.0483 (18) | 0.0449 (17) | 0.0014 (14) | −0.0064 (14) | 0.0077 (14) |
C12 | 0.0333 (16) | 0.0520 (19) | 0.0451 (17) | −0.0032 (14) | −0.0032 (13) | −0.0031 (15) |
C13 | 0.0441 (18) | 0.0426 (18) | 0.0560 (19) | −0.0116 (14) | −0.0027 (15) | 0.0030 (15) |
C14 | 0.0431 (17) | 0.0408 (17) | 0.0438 (16) | −0.0003 (14) | −0.0046 (14) | 0.0064 (14) |
Cl1—C12 | 1.733 (3) | C5—C6 | 1.376 (4) |
N1—C7 | 1.268 (3) | C5—H5 | 0.93 |
N1—N2 | 1.390 (3) | C6—H6 | 0.93 |
N2—C8 | 1.339 (3) | C7—H7 | 0.93 |
N2—H2A | 0.899 (10) | C8—C9 | 1.481 (3) |
O1—C4 | 1.363 (3) | C9—C10 | 1.385 (3) |
O1—H1 | 0.82 | C9—C14 | 1.387 (4) |
O2—C8 | 1.242 (3) | C10—C11 | 1.384 (4) |
C1—C6 | 1.385 (4) | C10—H10 | 0.93 |
C1—C2 | 1.392 (4) | C11—C12 | 1.369 (4) |
C1—C7 | 1.451 (4) | C11—H11 | 0.93 |
C2—C3 | 1.367 (4) | C12—C13 | 1.373 (4) |
C2—H2 | 0.93 | C13—C14 | 1.375 (4) |
C3—C4 | 1.383 (4) | C13—H13 | 0.93 |
C3—H3 | 0.93 | C14—H14 | 0.93 |
C4—C5 | 1.377 (4) | ||
C7—N1—N2 | 115.4 (2) | N1—C7—H7 | 119.3 |
C8—N2—N1 | 118.0 (2) | C1—C7—H7 | 119.3 |
C8—N2—H2A | 127 (2) | O2—C8—N2 | 121.5 (2) |
N1—N2—H2A | 114 (2) | O2—C8—C9 | 120.8 (2) |
C4—O1—H1 | 109.5 | N2—C8—C9 | 117.8 (2) |
C6—C1—C2 | 117.9 (2) | C10—C9—C14 | 118.8 (2) |
C6—C1—C7 | 120.4 (2) | C10—C9—C8 | 124.0 (2) |
C2—C1—C7 | 121.6 (2) | C14—C9—C8 | 117.2 (2) |
C3—C2—C1 | 121.2 (3) | C11—C10—C9 | 121.0 (2) |
C3—C2—H2 | 119.4 | C11—C10—H10 | 119.5 |
C1—C2—H2 | 119.4 | C9—C10—H10 | 119.5 |
C2—C3—C4 | 119.8 (3) | C12—C11—C10 | 118.7 (3) |
C2—C3—H3 | 120.1 | C12—C11—H11 | 120.6 |
C4—C3—H3 | 120.1 | C10—C11—H11 | 120.6 |
O1—C4—C5 | 123.3 (2) | C11—C12—C13 | 121.5 (3) |
O1—C4—C3 | 116.6 (2) | C11—C12—Cl1 | 119.8 (2) |
C5—C4—C3 | 120.1 (3) | C13—C12—Cl1 | 118.7 (2) |
C6—C5—C4 | 119.6 (3) | C12—C13—C14 | 119.5 (3) |
C6—C5—H5 | 120.2 | C12—C13—H13 | 120.2 |
C4—C5—H5 | 120.2 | C14—C13—H13 | 120.2 |
C5—C6—C1 | 121.3 (3) | C13—C14—C9 | 120.4 (3) |
C5—C6—H6 | 119.3 | C13—C14—H14 | 119.8 |
C1—C6—H6 | 119.3 | C9—C14—H14 | 119.8 |
N1—C7—C1 | 121.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O2i | 0.90 (1) | 2.08 (1) | 2.970 (3) | 171 (3) |
O1—H1···O2ii | 0.82 | 1.91 | 2.725 (3) | 170 |
C6—H6···Cg1iii | 0.93 | 2.88 | 3.726 (3) | 152 |
Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x+1/2, y+1/2, z; (iii) −x+1/2, −y+2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C14H11ClN2O2 |
Mr | 274.70 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 298 |
a, b, c (Å) | 26.251 (3), 12.376 (3), 7.786 (2) |
V (Å3) | 2529.5 (9) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.30 |
Crystal size (mm) | 0.13 × 0.12 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.963, 0.971 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11323, 2164, 1462 |
Rint | 0.078 |
(sin θ/λ)max (Å−1) | 0.592 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.116, 1.02 |
No. of reflections | 2164 |
No. of parameters | 176 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.27, −0.36 |
Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O2i | 0.90 (1) | 2.078 (11) | 2.970 (3) | 171 (3) |
O1—H1···O2ii | 0.82 | 1.91 | 2.725 (3) | 170 |
C6—H6···Cg1iii | 0.93 | 2.88 | 3.726 (3) | 152 |
Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x+1/2, y+1/2, z; (iii) −x+1/2, −y+2, z−1/2. |
Acknowledgements
The author acknowledges Key Laboratory Construction Support from the Education Office of Shanxi Province (project No. 05JS43).
References
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–S19. CrossRef Web of Science Google Scholar
Bernardo, K., Leppard, S., Robert, A., Commenges, G., Dahan, F. & Meunier, B. (1996). Inorg. Chem. 35, 387–396. CSD CrossRef PubMed CAS Web of Science Google Scholar
Bruker (2002). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Musie, G. T., Wei, M., Subramaniam, B. & Busch, D. H. (2001). Inorg. Chem. 40, 3336–3341. Web of Science CrossRef PubMed CAS Google Scholar
Paul, S., Barik, A. K., Peng, S. M. & Kar, S. K. (2002). Inorg. Chem. 41, 5803–5809. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yang, D.-S. (2007). J. Chem. Crystallogr. 37, 343–348. Web of Science CSD CrossRef CAS Google Scholar
Yang, D.-S. (2008a). Acta Cryst. E64, o1758. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yang, D.-S. (2008b). Acta Cryst. E64, o1759. Web of Science CSD CrossRef IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Schiff base compounds have been of great interest for a long time. These compounds play an important role in the development of coordination chemistry (Musie et al., 2001; Bernardo et al., 1996; Paul et al., 2002). Recently, we have reported a few Schiff base compounds (Yang, 2007, 2008a,b). As a further investigation of this work, the crystal structure of the title compound is reported here.
The molecule of the title compound displays a trans configuration with respect to the C═N double bond (Fig. 1). The dihedral angle between the two benzene rings is 12.8 (3)°. All the bonds are within normal ranges (Allen et al., 1987). The C7?N1 bond length of 1.268 (3) Å conforms to the value for a double bond. The bond length of 1.339 (3) Å between atoms C8 and N2 is intermediate between a C—N single bond and a C?N double bond, because of conjugation effects in the molecule.
In the crystal structure, molecules are linked through intermolecular O—H···O and N—H···O hydrogen bonds, and C—H···π interactions (Table 1), forming a three-dimensional network (Fig. 2).