organic compounds
2-[(E)-(4-Bromophenyl)iminomethyl]-4-chlorophenol
aDepartment of Chemistry, Taiyuan Normal College, Taiyuan, Shanxi 030031, People's Republic of China, and bInstitute of Molecular Science, Key Laboratory of Chemical Biology and Molecular Engineering of the Education Ministry, Shanxi University, Taiyuan, Shanxi 030006, People's Republic of China
*Correspondence e-mail: miaoli@sxu.edu.cn
In the title compound, C13H9BrClNO, the dihedral angle between the substituted benzene rings is 44.25 (11)°. There are strong intramolecular O—H⋯N hydrogen bonds, which generate S(6) rings, and also intermolecular Cl⋯Cl [3.431 (3) Å] and Br⋯ Br [3.846 (1) Å] contacts. The crystal packing a C—H⋯O and C—H⋯π interactions.
CCDC reference: 981552
Related literature
For background to the biological activity of et al. (2007); Li et al. (2007, 2011); Lu et al. (2011); Ma et al. (2011); Rehmana et al. (2008); Ritter et al. (2009); Vanco et al. (2008); Yuan et al. (2009, 2010). For related structures, see: Ardakani et al. (2011). For hydrogen-bond motifs, see: Bernstein et al. (1995).
see: AkmalExperimental
Crystal data
|
Data collection: SMART (Bruker, 2000); cell SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
CCDC reference: 981552
10.1107/S1600536814000981/fj2653sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814000981/fj2653Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814000981/fj2653Isup3.cml
A 0.1566 g (1.0 mmol) 5-chloro-salicylaldehyde in 15 ml of absolute ethanol was heated until thoroughly dissolved and 0.1720 g (1.0 mmol) of 4-bromo-aniline in 5 ml of absolute ethanol was added dropwise with a constant stirring. The reaction mixture was heated under refluxing for 3 h. After cooling slowly, the orange powder was separated out. Orange–red crystal was obtained from filter after two weeks.
H atoms attached to C and O of (I) were placed in geometrically idealized positions with Csp2—H = 0.93 Å and O—H = 0.84 Å and constrained to refine with Uiso(H) = 1.2Ueq(C) and Uiso(H) = 1.5Ueq(O).
Data collection: SMART (Bruker, 2000); cell
SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: publCIF (Westrip, 2010).Fig. 1. A view of the structure of (I), with displacement ellipsoids drawn at the 30% probability level. Dashed line indicates hydrogen-bonding interaction. | |
Fig. 2. The packing diagram of the title compound, showing the intermolecular O—H···N and intermolecular Cl···Cl, Br···Br and C—H···O interactions (dotted lines). |
C13H9BrClNO | F(000) = 1232 |
Mr = 310.57 | Dx = 1.720 Mg m−3 |
Orthorhombic, Pccn | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ab 2ac | Cell parameters from 4170 reflections |
a = 6.9964 (15) Å | θ = 2.2–22.6° |
b = 55.786 (12) Å | µ = 3.63 mm−1 |
c = 6.1443 (14) Å | T = 298 K |
V = 2398.1 (9) Å3 | Block, colourless |
Z = 8 | 0.30 × 0.25 × 0.20 mm |
Bruker SMART 1K CCD area-detector diffractometer | 3013 independent reflections |
Radiation source: fine-focus sealed tube | 2056 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.061 |
ω scans | θmax = 28.4°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2000) | h = −9→9 |
Tmin = 0.409, Tmax = 0.530 | k = −74→74 |
30095 measured reflections | l = −8→8 |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.128 | H-atom parameters constrained |
S = 1.14 | w = 1/[σ2(Fo2) + (0.027P)2 + 7.4937P] where P = (Fo2 + 2Fc2)/3 |
3013 reflections | (Δ/σ)max = 0.001 |
155 parameters | Δρmax = 0.42 e Å−3 |
0 restraints | Δρmin = −0.95 e Å−3 |
C13H9BrClNO | V = 2398.1 (9) Å3 |
Mr = 310.57 | Z = 8 |
Orthorhombic, Pccn | Mo Kα radiation |
a = 6.9964 (15) Å | µ = 3.63 mm−1 |
b = 55.786 (12) Å | T = 298 K |
c = 6.1443 (14) Å | 0.30 × 0.25 × 0.20 mm |
Bruker SMART 1K CCD area-detector diffractometer | 3013 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2000) | 2056 reflections with I > 2σ(I) |
Tmin = 0.409, Tmax = 0.530 | Rint = 0.061 |
30095 measured reflections |
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.128 | H-atom parameters constrained |
S = 1.14 | Δρmax = 0.42 e Å−3 |
3013 reflections | Δρmin = −0.95 e Å−3 |
155 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 | ||
Br1 | −0.03618 (9) | 0.228348 (8) | −0.07815 (11) | 0.0634 (2) | |
C1 | −0.0360 (6) | 0.08714 (7) | 0.5859 (7) | 0.0339 (8) | |
C2 | −0.0711 (6) | 0.06455 (8) | 0.6715 (7) | 0.0404 (10) | |
H2 | −0.1186 | 0.0631 | 0.8123 | 0.049* | |
C3 | −0.0364 (6) | 0.04435 (7) | 0.5506 (8) | 0.0426 (11) | |
H3 | −0.0609 | 0.0293 | 0.6092 | 0.051* | |
C4 | 0.0346 (6) | 0.04637 (7) | 0.3425 (7) | 0.0372 (10) | |
C5 | 0.0691 (6) | 0.06843 (7) | 0.2537 (7) | 0.0333 (9) | |
H5 | 0.1169 | 0.0695 | 0.1129 | 0.040* | |
C6 | 0.0332 (6) | 0.08932 (7) | 0.3722 (6) | 0.0306 (8) | |
C7 | 0.0538 (6) | 0.11247 (7) | 0.2675 (7) | 0.0335 (9) | |
H7 | 0.0897 | 0.1132 | 0.1219 | 0.040* | |
C8 | 0.0157 (5) | 0.15412 (7) | 0.2599 (7) | 0.0304 (8) | |
C9 | −0.0626 (6) | 0.15603 (7) | 0.0518 (7) | 0.0335 (9) | |
H9 | −0.1044 | 0.1424 | −0.0209 | 0.040* | |
C10 | −0.0780 (6) | 0.17821 (7) | −0.0459 (7) | 0.0359 (9) | |
H10 | −0.1315 | 0.1795 | −0.1839 | 0.043* | |
C11 | −0.0140 (6) | 0.19838 (7) | 0.0610 (8) | 0.0392 (10) | |
C12 | 0.0610 (6) | 0.19682 (7) | 0.2681 (8) | 0.0401 (10) | |
H12 | 0.1013 | 0.2106 | 0.3402 | 0.048* | |
C13 | 0.0759 (6) | 0.17470 (7) | 0.3676 (7) | 0.0352 (9) | |
H13 | 0.1265 | 0.1736 | 0.5072 | 0.042* | |
Cl1 | 0.0736 (2) | 0.02081 (2) | 0.1879 (2) | 0.0614 (4) | |
N1 | 0.0235 (5) | 0.13186 (6) | 0.3721 (5) | 0.0322 (7) | |
O1 | −0.0721 (5) | 0.10666 (5) | 0.7096 (5) | 0.0474 (8) | |
H1 | −0.0470 | 0.1188 | 0.6401 | 0.071* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0722 (4) | 0.0352 (2) | 0.0829 (4) | 0.0069 (2) | −0.0019 (3) | 0.0149 (3) |
C1 | 0.035 (2) | 0.038 (2) | 0.029 (2) | −0.0004 (18) | −0.0007 (18) | −0.0038 (17) |
C2 | 0.036 (2) | 0.053 (3) | 0.032 (2) | −0.004 (2) | 0.002 (2) | 0.007 (2) |
C3 | 0.046 (2) | 0.034 (2) | 0.048 (3) | −0.0034 (19) | 0.000 (2) | 0.0120 (19) |
C4 | 0.039 (2) | 0.0318 (19) | 0.041 (2) | 0.0016 (18) | −0.001 (2) | −0.0023 (17) |
C5 | 0.037 (2) | 0.0304 (19) | 0.032 (2) | 0.0017 (17) | 0.0008 (19) | −0.0019 (16) |
C6 | 0.030 (2) | 0.0345 (19) | 0.028 (2) | 0.0024 (17) | −0.0034 (17) | 0.0023 (15) |
C7 | 0.034 (2) | 0.038 (2) | 0.029 (2) | 0.0013 (17) | 0.0027 (19) | 0.0018 (17) |
C8 | 0.029 (2) | 0.0299 (18) | 0.032 (2) | 0.0004 (15) | 0.0030 (17) | −0.0019 (16) |
C9 | 0.039 (2) | 0.0289 (18) | 0.033 (2) | −0.0029 (17) | −0.0012 (19) | −0.0041 (16) |
C10 | 0.033 (2) | 0.038 (2) | 0.037 (2) | 0.0031 (17) | 0.0000 (19) | −0.0019 (18) |
C11 | 0.036 (2) | 0.0315 (19) | 0.050 (3) | 0.0041 (17) | 0.006 (2) | 0.0035 (19) |
C12 | 0.042 (2) | 0.0299 (19) | 0.048 (3) | −0.0017 (18) | −0.003 (2) | −0.0077 (18) |
C13 | 0.033 (2) | 0.037 (2) | 0.036 (2) | −0.0005 (17) | −0.0029 (18) | −0.0080 (17) |
Cl1 | 0.0858 (10) | 0.0333 (5) | 0.0652 (8) | −0.0007 (6) | 0.0074 (8) | −0.0081 (6) |
N1 | 0.0343 (18) | 0.0305 (15) | 0.0318 (18) | −0.0003 (14) | −0.0008 (15) | −0.0009 (14) |
O1 | 0.069 (2) | 0.0394 (16) | 0.0342 (17) | 0.0003 (16) | 0.0096 (17) | −0.0042 (13) |
Br1—C11 | 1.884 (4) | C7—H7 | 0.9300 |
C1—O1 | 1.352 (5) | C8—C13 | 1.390 (5) |
C1—C2 | 1.387 (6) | C8—C9 | 1.395 (6) |
C1—C6 | 1.405 (6) | C8—N1 | 1.422 (5) |
C2—C3 | 1.371 (6) | C9—C10 | 1.379 (5) |
C2—H2 | 0.9300 | C9—H9 | 0.9300 |
C3—C4 | 1.377 (6) | C10—C11 | 1.378 (6) |
C3—H3 | 0.9300 | C10—H10 | 0.9300 |
C4—C5 | 1.367 (6) | C11—C12 | 1.379 (7) |
C4—Cl1 | 1.735 (4) | C12—C13 | 1.381 (6) |
C5—C6 | 1.397 (5) | C12—H12 | 0.9300 |
C5—H5 | 0.9300 | C13—H13 | 0.9300 |
C6—C7 | 1.450 (5) | O1—H1 | 0.8200 |
C7—N1 | 1.276 (5) | ||
O1—C1—C2 | 119.1 (4) | C13—C8—C9 | 119.5 (4) |
O1—C1—C6 | 121.3 (4) | C13—C8—N1 | 118.6 (4) |
C2—C1—C6 | 119.6 (4) | C9—C8—N1 | 121.7 (3) |
C3—C2—C1 | 120.6 (4) | C10—C9—C8 | 119.8 (4) |
C3—C2—H2 | 119.7 | C10—C9—H9 | 120.1 |
C1—C2—H2 | 119.7 | C8—C9—H9 | 120.1 |
C2—C3—C4 | 120.0 (4) | C11—C10—C9 | 120.0 (4) |
C2—C3—H3 | 120.0 | C11—C10—H10 | 120.0 |
C4—C3—H3 | 120.0 | C9—C10—H10 | 120.0 |
C5—C4—C3 | 120.5 (4) | C10—C11—C12 | 120.8 (4) |
C5—C4—Cl1 | 119.6 (3) | C10—C11—Br1 | 118.8 (3) |
C3—C4—Cl1 | 119.9 (3) | C12—C11—Br1 | 120.4 (3) |
C4—C5—C6 | 120.8 (4) | C11—C12—C13 | 119.6 (4) |
C4—C5—H5 | 119.6 | C11—C12—H12 | 120.2 |
C6—C5—H5 | 119.6 | C13—C12—H12 | 120.2 |
C5—C6—C1 | 118.5 (4) | C12—C13—C8 | 120.3 (4) |
C5—C6—C7 | 119.6 (4) | C12—C13—H13 | 119.9 |
C1—C6—C7 | 121.7 (4) | C8—C13—H13 | 119.9 |
N1—C7—C6 | 121.0 (4) | C7—N1—C8 | 120.2 (3) |
N1—C7—H7 | 119.5 | C1—O1—H1 | 109.5 |
C6—C7—H7 | 119.5 | ||
O1—C1—C2—C3 | 179.9 (4) | C1—C6—C7—N1 | 5.4 (6) |
C6—C1—C2—C3 | 0.9 (6) | C13—C8—C9—C10 | 0.6 (6) |
C1—C2—C3—C4 | 0.3 (7) | N1—C8—C9—C10 | 176.0 (4) |
C2—C3—C4—C5 | −0.8 (7) | C8—C9—C10—C11 | 0.7 (6) |
C2—C3—C4—Cl1 | −178.6 (4) | C9—C10—C11—C12 | −1.8 (6) |
C3—C4—C5—C6 | 0.1 (6) | C9—C10—C11—Br1 | 179.7 (3) |
Cl1—C4—C5—C6 | 178.0 (3) | C10—C11—C12—C13 | 1.4 (7) |
C4—C5—C6—C1 | 1.1 (6) | Br1—C11—C12—C13 | 179.9 (3) |
C4—C5—C6—C7 | −174.2 (4) | C11—C12—C13—C8 | 0.0 (6) |
O1—C1—C6—C5 | 179.5 (4) | C9—C8—C13—C12 | −1.0 (6) |
C2—C1—C6—C5 | −1.6 (6) | N1—C8—C13—C12 | −176.6 (4) |
O1—C1—C6—C7 | −5.3 (6) | C6—C7—N1—C8 | −170.4 (3) |
C2—C1—C6—C7 | 173.6 (4) | C13—C8—N1—C7 | −148.7 (4) |
C5—C6—C7—N1 | −179.4 (4) | C9—C8—N1—C7 | 35.8 (6) |
Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 benzene rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.82 | 1.87 | 2.593 (4) | 147 |
C2—H2···Cg1i | 0.93 | 2.82 | 3.489 (5) | 129 |
C5—H5···Cg1ii | 0.93 | 2.85 | 3.513 (5) | 129 |
C10—H10···Cg2iii | 0.93 | 2.75 | 3.460 (5) | 133 |
C13—H13···Cg2iv | 0.93 | 2.78 | 3.473 (5) | 132 |
Symmetry codes: (i) −x+1/2, y, z−1/2; (ii) −x+3/2, y, z−3/2; (iii) −x+1/2, y, z−3/2; (iv) −x+3/2, y, z−1/2. |
Cg1 and Cg2 are the centroids of the C1–C6 and C8–C13 benzene rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.82 | 1.87 | 2.593 (4) | 147 |
C2—H2···Cg1i | 0.93 | 2.82 | 3.489 (5) | 129 |
C5—H5···Cg1ii | 0.93 | 2.85 | 3.513 (5) | 129 |
C10—H10···Cg2iii | 0.93 | 2.75 | 3.460 (5) | 133 |
C13—H13···Cg2iv | 0.93 | 2.78 | 3.473 (5) | 132 |
Symmetry codes: (i) −x+1/2, y, z−1/2; (ii) −x+3/2, y, z−3/2; (iii) −x+1/2, y, z−3/2; (iv) −x+3/2, y, z−1/2. |
Acknowledgements
This work was supported financially by the National Natural Science Foundation of China (grant Nos. 21001070 and 21171109), the Specialized Research Fund for the Doctoral Program of Higher Education (grant No. 20111401110002) and the Natural Science Foundation of Shanxi Province (grant Nos. 2010011011-2, 2011011009-1 and 2011021006-2).
References
Akmal, S. G., Mohsen, S. A., Atiat, S. B. & Said, M. T. (2007). Spectrochim. Acta Part A, 67, 114–121. Google Scholar
Ardakani, A. A., Kia, R., Kargar, H. & Tahir, M. N. (2011). Acta Cryst. E67, o597. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Li, Y., Lu, L.-P., Zhu, M.-L., Wang, Q.-M., Yuan, C.-X., Xing, S., Fu, X.-Q. & Mei, Y.-H. (2011). BioMetals, 24, 993–1004. Web of Science CrossRef CAS PubMed Google Scholar
Li, Y.-G., Shi, D.-H., Zhu, H.-L., Yan, H. & Ng, S. W. (2007). Inorg. Chim. Acta, 360, 2881–2889. Web of Science CSD CrossRef CAS Google Scholar
Lu, L.-P., Yue, J.-J., Yuan, C.-X., Zhu, M.-L., Han, H., Liu, Z.-W. & Guo, M.-L. (2011). J. Inorg. Biochem. 105, 1323–1328. Web of Science CrossRef CAS PubMed Google Scholar
Ma, L., Lu, L.-P., Zhu, M.-L., Wang, Q.-M., Li, Y., Xing, S., Fu, X.-Q., Gao, Z.-Q. & Dong, Y.-H. (2011). Dalton Trans. 40, 6532–6540. Web of Science CSD CrossRef CAS PubMed Google Scholar
Rehmana, W., Samana, F. & Ahmadb, I. (2008). Russ. J. Coord. Chem. 34, 678–682. Google Scholar
Ritter, E., Przybylski, P., Brzezinski, B. & Bartl, F. (2009). Curr. Org. Chem. 13, 241–249. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2000). 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
Vanco, J., Marek, J., Travnicek, Z., Racanska, E., Muselik, J. & Svajlenova, O. (2008). J. Inorg. Biochem. 102, 595–605. Web of Science PubMed CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yuan, C., Lu, L., Gao, X., Wu, Y., Guo, M., Li, Y., Fu, X. & Zhu, M. (2009). J. Biol. Inorg. Chem. 14, 841–851. Web of Science CSD CrossRef PubMed CAS Google Scholar
Yuan, C., Lu, L., Wu, Y., Liu, Z., Guo, M., Xing, S., Fu, X. & Zhu, M. (2010). J. Inorg. Biochem. 104, 978–986. Web of Science CSD CrossRef CAS PubMed 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 bases are condensed by primary amines and carbonyl compounds, containing strong electronegative with atoms O and N, thus it is easy to coordinate with the metal ions to form stable complexes (Akmal et al., 2007; Rehmana et al., 2008). It is reported that metal complexes of Schiff base derivatives have a variety of important biological activities, such as anti-bacterial, anti-cancer, anti-tumor, hypoglycemic and so on (Vanco et al., 2008; Li et al., 2007; Ritter et al., 2009). Our reports indicated that copper and vanadium complexes of Schiff bases are potential inhitors over protein tyrosine phosphatases (Li et al., 2011; Lu et al., 2011; Ma et al., 2011; Yuan et al., 2009, 2010).
We report here the synthesis and characterization a potentially bidentate Schiff base derivative, (I), and prepared from the condensation reaction of an equimolar proportion of 5-chloro-salicylaldehyde and 4-bromo-aniline in absolute ethanol. The molecular structure is depicted in Fig. 1. X-ray structural analysis confirmed that in the title compound, (I), the dihedral angle between the substituted benzene rings is nearly 44.25 (11)°, similar to the compound 4-bromo-2-[(E)-(4-chlorophenyl)iminomethyl]phenol (Ardakani et al., 2011). In the crystal, there are strong intramolecular O—H···N hydrogen bonds with a distance of 2.593 (5) Å between donor and acceptor, which generate S(6) ring and intermolecular Cl1···Cl1i [3.430 (2) Å, i -x, -y, -z] as well as Br1···Br1ii [3.846 (1) Å, ii 2 - x, -y, -z] contacts. The crystal packing is further stabilized by intermolecular C—H···O and C—H···π interactions (Table 1).