(E)-3-[(3-Bromo­phen­yl)imino­meth­yl]benzene-1,2-diol: a combined X-ray and computational structural study

Keleşoğlu, Z.; Büyükgüngör, O.; Albayrak, Ç.; Odabaşoğlu, M.

doi:10.1107/S1600536809035053

Volume 65
Part 10
Pages o2410-o2411
October 2009

Received 13 August 2009
Accepted 31 August 2009
Online 9 September 2009

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.004 Å
R = 0.033
wR = 0.078
Data-to-parameter ratio = 13.7
Details

(E)-3-[(3-Bromophenyl)iminomethyl]benzene-1,2-diol: a combined X-ray and computational structural study

Zeynep Kelesoglu,^a Orhan Büyükgüngör,^a ^* Çigdem Albayrak ^b and Mustafa Odabasoglu ^c

^aDepartment of Physics, Ondokuz Mayis University, Samsun, Turkey,^bSinop Faculty of Education, Sinop University, Sinop, Turkey, and ^cChemical Technology Program, Denizli Higher Vocational School, Pamukkale University, Denizli, Turkey
Correspondence e-mail: zeynep.kelesoglu@omu.edu.tr

The title compound, C₁₃H₁₀BrNO₂, exists as an enol-imine form in the crystal and adopts an E configuration with respect to the C=N double bond. The molecule is close to planar, with a dihedral angle of 6.88 (14)° between the aromatic rings. Intramolecular O-HN and O-HO hydrogen bonds generate S(6) and S(5) ring motifs, respectively. The crystal structure is stabilized by intermolecular O-HO hydrogen-bond interactions, forming R₂²(10) and R₂²(20) chains along [100]. ab initio Hartree-Fock (HF), density-functional theory (DFT) and semi-empirical (AM1 and PM3) calculations and full-geometry optimizations were also performed. Although there are some discrepancies between the experimental and calculated parameters, caused presumably by the O-HO hydrogen-bond interactions, there is an acceptable general agreement between them.

Related literature

For general background to Schiff base compounds in coordination chemistry, see: Chen et al. (2008); May et al. (2004); Weber et al. (2007). For background to DFT calculations, see: Becke (1988, 1993); Lee et al. (1988); Schmidt & Polik et al. (2007); Friesner et al. (2005); Liu et al. (2004). For a related structure, see: Cao et al. (2009); Temel et al. (2007). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₁₃H₁₀BrNO₂
M_r = 292.13
Orthorhombic, P b c a
a = 4.7411 (2) Å
b = 18.9447 (6) Å
c = 26.1417 (10) Å
V = 2348.01 (15) Å³
Z = 8
Mo K radiation
= 3.50 mm^-1
T = 296 K
0.66 × 0.38 × 0.10 mm

Data collection

Stoe IPDS-II diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) T_min = 0.229, T_max = 0.735
7185 measured reflections
2212 independent reflections
1764 reflections with I > 2(I)
R_int = 0.040

Refinement

R[F² > 2(F²)] = 0.033
wR(F²) = 0.078
S = 1.05
2212 reflections
162 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.33 e Å^-3
_min = -0.42 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1N1	0.87 (4)	1.81 (4)	2.606 (3)	151 (3)
O2-H2O1	0.78 (4)	2.31 (5)	2.718 (3)	113 (4)
O2-H2O2ⁱ	0.78 (4)	2.48 (5)	3.124 (3)	141 (5)
O2-H2O1ⁱⁱ	0.78 (4)	2.46 (4)	2.986 (3)	126 (4)
Symmetry codes: (i) $[x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ .

Table 2
Selected geometric parameters (Å, °) from the X-ray structure and calculated by AM1, PM3, HF and DFT methods

Parameters	X-ray	AM1	PM3	HF*	DFT/B3LYP*
C1-C7	1.447 (4)	1.4659	1.4592	1.4655	1.4472
C8-N1	1.416 (3)	1.4103	1.431	1.4082	1.4071
C7-N1	1.278 (3)	1.2923	1.3028	1.2626	1.2947
C2-O1	1.355 (3)	1.3711	1.3612	1.3414	1.35
C3-O2	1.358 (3)	1.3749	1.3695	1.3472	1.3601
C10-Br1	1.900 (2)	1.8743	1.8676	1.899	1.9138

O1-C2-C1	122.8 (2)	126.384	124.0177	124.2818	123.5134
N1-C7-C1	122.1 (2)	123.752	119.6344	123.297	121.9975
O2-C3-C4	119.9 (2)	117.2553	115.9182	119.9887	120.7548
O1-C2-C3	117.5 (2)	113.7932	116.4985	115.8053	116.4318
O2-C3-C2	120.5 (2)	122.181	123.9237	119.978	119.4331
C7-N1-C8	121.6 (2)	121.8246	122.1744	120.3634	121.3341

C12-C13-H13	119.6	119.7856	119.8376	120.8687	121.0058
C8-C13-H13	119.6	120.1274	120.1469	119.0149	118.759
C1-C7-N1-C8	179.7 (2)	-179.2308	179.9974	-178.6515	-177.5099
C9-C8-N1-C7	7.9 (4)	34.1092	0.0009	44.5418	35.1166
C2-C1-C7-N1	-1.6 (4)	2.6542	0.0087	0.8066	0.3196
N1-C8-C9-C10	-179.9 (2)	-177.3895	179.9976	179.3862	179.4699
C8-C9-C10-Br1	-179.41 (19)	-179.8397	-180.0011	-179.9136	-179.7804
*6-31G(d,p).

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); 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, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and GAUSSIAN (Frisch et al., 2004).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SI2198 ).

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayis University, Turkey, for the use of the Stoe IPDSII diffractometer (purchased under grant F.279 of the University Research Fund).

References

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organic compounds