4-Bromo-2-[(E)-{[4-nitro-2-(trifluoro­meth­yl)phen­yl]imino}­meth­yl]phenol

Akkurt, M.; Kennedy, A.R.; Mohamed, S.K.; Abdelhamid, A.A.; Miller, G.J.

doi:10.1107/S1600536812042262

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3168

doi:10.1107/S1600536812042262

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4-Bromo-2-[(E)-{[4-nitro-2-(trifluoromethyl)phenyl]imino}methyl]phenol

Mehmet Akkurt,^a ^* Alan R. Kennedy,^b Shaaban K. Mohamed,^c Antar A. Abdelhamid ^c and Gary J. Miller ^d

^aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^bDepartment of Pure & Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, Scotland, ^cChemistry and Environmental Division, Manchester Metropolitan University, Manchester, M1 5GD, England, and ^dAnalytical Sciences, Manchester Metropolitan University, Manchester, M1 5GD, England
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 7 October 2012; accepted 9 October 2012; online 20 October 2012)

Except two F atoms of the –CF₃ group, the title compound, C₁₄H₈BrF₃N₂O₃, has an almost planar conformation, the dihedral angle between the aromatic rings being 3.60 (16)°. The molecule adopts the enol–imine tautomeric form, with an intramolecular O—H⋯N hydrogen bond, which generates an S(6) ring motif. In the crystal, face-to-face π–π stacking [centroid–centroid distances = 3.669 (2) and 3.732 (2) Å] between the aromatic rings of the molecules, which lie in sheets parallel to (202), help to establish the packing.

Related literature

For the biological activity of fluorine-containing compounds, see: Blair et al. (2000 ); Chawla et al. (2012 ); Bella et al. (2004 ); Chandra & Kumar (2005 ); Yang et al. (2000 ). For the synthesis of a similar azomethine compound, see: Mohamed et al. (2012 ). For the graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₄H₈BrF₃N₂O₃
M_r = 389.12
Monoclinic, P 2₁ /n
a = 7.3596 (5) Å
b = 16.4625 (10) Å
c = 11.2599 (6) Å
β = 94.955 (5)°
V = 1359.12 (14) Å³
Z = 4
Mo Kα radiation
μ = 3.08 mm⁻¹
T = 123 K
0.20 × 0.18 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.546, T_max = 0.575
6329 measured reflections
3149 independent reflections
2165 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.090
S = 1.02
3149 reflections
203 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.59 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1O⋯N1	0.84	1.88	2.623 (4)	146

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812042262/xu5632sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812042262/xu5632Isup2.hkl

checkCIF report

Comment top

A great number of Schiff base complexes with metals have provoked wide interest because they possess a diverse spectrum of biological and pharmaceutical activities, such as antitumor and anti-oxidative activities, as well as the inhibition of lipid peroxidation (Bella et al., 2004; Chandra & Kumar, 2005; Yang et al., 2000). Fluorine can dramatically change the properties of biologically active compounds and can influence the metabolism and distribution of drug molecules in the body (Blair et al., 2000). Recently, SAR studies revealed that the presence of a fluoro group had a marked influence on the antibacterial activity (Chawla et al., 2012). Such facts and further to our studies on synthesis of bio-active molecules we herein report the synthesis and crystal structure of a new potential bio-active fluorinated azomethine compound (I).

Fig. 1 shows the title compound (I) with the enol-imine tautomeric form, which has an intramolecular O— H···N hydrogen bond forming an S(6) motif (Bernstein et al., 1995; Table 1). The C6—O3 single bond of 1.354 (4) Å and the C7═N1 double bond of 1.293 (4) Å verify the enol-imine form. These distances and the values of the other geometric parameters are in the normal range and are comparable with those of a similar compound reported previously (Mohamed et al., 2012). The two aromatic rings (C1–C6 and C8–C13) make a dihedral angle of 3.60 (16)° with each other. The C1—C7—N1—C8, O1—N2—C11—C10, O2—N2—C11—C10, C14–C9—C8—N1, C8—N1—C7—C1, C7—C1—C6—O3 and C1—C2—C3—Br1 torsion angles are 178.1 (3), 2.4 (4), 175.8 (3), -1.4 (5), -178.1 (3), 0.0 (6) and 179.2 (3) °, respectively. Therefore, the whole molecule of (I), except the F1 and F3 atoms of the –CF₃ group, is almostly planar.

The crystal structure is stabilized by face-to-face π-π stacking interactions [Cg1···Cg2(1 - x, -y, 2 - z) = 3.669 (2) Å and Cg1···Cg2(2 - x, -y, 2 - z) = 3.732 (2) Å] between the Cg1 and Cg2 centroids of the C1–C6 and C8–C13 aromatic rings of the molecules to form two-dimensional sheets parallel to the (202) plane (Fig. 2 & Fig. 3).

Related literature top

For the biological activity of fluorine-containing compounds, see: Blair et al. (2000); Chawla et al. (2012); Bella et al. (2004); Chandra & Kumar (2005); Yang et al. (2000). For the synthesis of a similar azomethine compound, see: Mohamed et al. (2012). For the graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995).

Experimental top

The title compound was unexpectedly obtained from a three component reaction of 0.01 mol 4-nitro-2-(trifluoromethyl)aniline, 0.01 mol 5-bromosalicyaldehyde and 0.01 mol 5-phenyl-1,3-cyclohexanedione in 50 ml ethanol. The reaction mixture was refluxed for 7 h at 350 K. The solid product that obtained on cooling was filtered off, washed with cold ethanol and dried. The crude product was recrystallized from a mixture of ethanol and acetone (10:1 vv) to afford a good quality crystals suitable for X-ray difraction after two days of slow evaporation at room temperature. [Yield 83%; Mp. 511 K].

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); 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 PLATON (Spek, 2009).

Figures top

	Fig. 1. The title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
	Fig. 2. View of the packing and hydrogen bonding of (I) down a axis. H atoms not involved in hydrogen bonding have been omitted for clarity.
	Fig. 3. View of the packing and hydrogen bonding of (I) down b axis. H atoms not involved in hydrogen bonding have been omitted for clarity.

4-Bromo-2-[(E)-{[4-nitro-2-(trifluoromethyl)phenyl]imino}methyl]phenol top

Crystal data top

C₁₄H₈BrF₃N₂O₃	F(000) = 768
M_r = 389.12	D_x = 1.902 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1836 reflections
a = 7.3596 (5) Å	θ = 3.2–29.0°
b = 16.4625 (10) Å	µ = 3.08 mm⁻¹
c = 11.2599 (6) Å	T = 123 K
β = 94.955 (5)°	Cut rod, yellow
V = 1359.12 (14) Å³	0.20 × 0.18 × 0.18 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	3149 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2165 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
Detector resolution: 16.0727 pixels mm^-1	θ_max = 29.0°, θ_min = 3.2°
ω scans	h = −9→8
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −18→22
T_min = 0.546, T_max = 0.575	l = −14→15
6329 measured reflections

Refinement top

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.090	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0233P)²] where P = (F_o² + 2F_c²)/3
3149 reflections	(Δ/σ)_max < 0.001
203 parameters	Δρ_max = 0.51 e Å⁻³
1 restraint	Δρ_min = −0.59 e Å⁻³

Crystal data top

C₁₄H₈BrF₃N₂O₃	V = 1359.12 (14) Å³
M_r = 389.12	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.3596 (5) Å	µ = 3.08 mm⁻¹
b = 16.4625 (10) Å	T = 123 K
c = 11.2599 (6) Å	0.20 × 0.18 × 0.18 mm
β = 94.955 (5)°

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	3149 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	2165 reflections with I > 2σ(I)
T_min = 0.546, T_max = 0.575	R_int = 0.043
6329 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	1 restraint
wR(F²) = 0.090	H-atom parameters constrained
S = 1.02	Δρ_max = 0.51 e Å⁻³
3149 reflections	Δρ_min = −0.59 e Å⁻³
203 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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

	x	y	z	U_iso*/U_eq
Br1	0.40760 (6)	0.10935 (3)	0.52512 (3)	0.0305 (2)
F1	0.7671 (3)	0.08414 (14)	1.28090 (17)	0.0313 (8)
F2	1.0022 (3)	0.05148 (15)	1.39501 (17)	0.0404 (9)
F3	1.0339 (3)	0.09587 (14)	1.21958 (18)	0.0321 (8)
O1	1.1326 (3)	−0.22498 (18)	1.4389 (2)	0.0299 (9)
O2	1.0746 (4)	−0.31205 (17)	1.2960 (2)	0.0286 (9)
O3	0.7242 (4)	0.17073 (17)	1.02757 (19)	0.0262 (9)
N1	0.7788 (4)	0.01384 (19)	1.0499 (2)	0.0168 (7)
N2	1.0692 (4)	−0.2434 (2)	1.3380 (3)	0.0231 (11)
C1	0.6384 (5)	0.0741 (2)	0.8725 (3)	0.0160 (11)
C2	0.5635 (4)	0.0613 (2)	0.7551 (3)	0.0185 (11)
C3	0.5065 (5)	0.1256 (3)	0.6850 (3)	0.0192 (11)
C4	0.5184 (5)	0.2040 (3)	0.7277 (3)	0.0220 (12)
C5	0.5917 (5)	0.2182 (2)	0.8437 (3)	0.0210 (12)
C6	0.6520 (5)	0.1540 (2)	0.9156 (3)	0.0176 (11)
C7	0.6997 (4)	0.0045 (2)	0.9437 (3)	0.0168 (7)
C8	0.8434 (4)	−0.0537 (2)	1.1180 (3)	0.0145 (11)
C9	0.9215 (5)	−0.0375 (2)	1.2358 (3)	0.0158 (11)
C10	0.9916 (4)	−0.1002 (2)	1.3070 (3)	0.0185 (11)
C11	0.9869 (4)	−0.1777 (2)	1.2628 (3)	0.0165 (11)
C12	0.9119 (5)	−0.1958 (2)	1.1491 (3)	0.0194 (12)
C13	0.8421 (5)	−0.1338 (2)	1.0781 (3)	0.0190 (11)
C14	0.9282 (5)	0.0480 (3)	1.2828 (3)	0.0225 (12)
H1O	0.75720	0.12730	1.06220	0.0390*
H2	0.55230	0.00760	0.72440	0.0220*
H4	0.47670	0.24810	0.67820	0.0260*
H5	0.60030	0.27220	0.87360	0.0250*
H7	0.68160	−0.04870	0.91210	0.0200*
H10	1.04260	−0.08970	1.38590	0.0220*
H12	0.90880	−0.25020	1.12080	0.0230*
H13	0.79150	−0.14570	0.99960	0.0230*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0418 (3)	0.0288 (3)	0.0189 (2)	0.0038 (2)	−0.0083 (2)	0.0014 (2)
F1	0.0389 (14)	0.0225 (14)	0.0323 (13)	0.0074 (12)	0.0023 (10)	−0.0076 (11)
F2	0.0708 (18)	0.0249 (16)	0.0215 (12)	0.0036 (15)	−0.0195 (11)	−0.0031 (11)
F3	0.0407 (14)	0.0180 (14)	0.0370 (13)	−0.0091 (12)	−0.0002 (10)	−0.0010 (11)
O1	0.0367 (17)	0.0287 (18)	0.0221 (14)	−0.0014 (15)	−0.0098 (11)	0.0078 (14)
O2	0.0364 (17)	0.0168 (17)	0.0325 (15)	0.0032 (15)	0.0019 (12)	0.0047 (13)
O3	0.0387 (17)	0.0174 (16)	0.0206 (14)	0.0006 (15)	−0.0082 (11)	0.0014 (12)
N1	0.0190 (12)	0.0145 (13)	0.0168 (11)	−0.0024 (11)	0.0008 (9)	0.0019 (11)
N2	0.0215 (18)	0.023 (2)	0.0249 (18)	0.0009 (17)	0.0021 (13)	0.0074 (16)
C1	0.0146 (19)	0.017 (2)	0.0164 (18)	−0.0012 (17)	0.0015 (14)	0.0063 (17)
C2	0.0190 (19)	0.015 (2)	0.021 (2)	−0.0019 (18)	−0.0007 (14)	−0.0029 (17)
C3	0.0156 (19)	0.024 (2)	0.0178 (19)	−0.0020 (18)	−0.0004 (14)	0.0031 (17)
C4	0.020 (2)	0.023 (2)	0.023 (2)	−0.0011 (19)	0.0022 (15)	0.0039 (18)
C5	0.025 (2)	0.013 (2)	0.025 (2)	0.0003 (18)	0.0022 (15)	0.0016 (17)
C6	0.0170 (19)	0.016 (2)	0.0198 (19)	−0.0017 (18)	0.0014 (14)	0.0005 (17)
C7	0.0190 (12)	0.0145 (13)	0.0168 (11)	−0.0024 (11)	0.0008 (9)	0.0019 (11)
C8	0.0136 (18)	0.016 (2)	0.0139 (18)	0.0001 (17)	0.0015 (13)	0.0036 (16)
C9	0.0169 (19)	0.016 (2)	0.0144 (18)	−0.0003 (17)	0.0015 (14)	0.0020 (16)
C10	0.0168 (19)	0.025 (2)	0.0136 (18)	−0.0014 (19)	0.0009 (13)	0.0002 (17)
C11	0.0138 (19)	0.018 (2)	0.0177 (18)	0.0029 (17)	0.0018 (14)	0.0057 (17)
C12	0.022 (2)	0.012 (2)	0.024 (2)	−0.0020 (18)	0.0015 (15)	−0.0028 (17)
C13	0.028 (2)	0.014 (2)	0.0139 (18)	−0.0011 (18)	−0.0037 (15)	−0.0018 (16)
C14	0.029 (2)	0.017 (2)	0.020 (2)	−0.001 (2)	−0.0071 (16)	0.0025 (17)

Geometric parameters (Å, º) top

Br1—C3	1.902 (3)	C4—C5	1.389 (5)
F1—C14	1.325 (5)	C5—C6	1.381 (5)
F2—C14	1.333 (4)	C8—C13	1.393 (5)
F3—C14	1.352 (5)	C8—C9	1.425 (5)
O1—N2	1.228 (4)	C9—C10	1.379 (5)
O2—N2	1.227 (4)	C9—C14	1.503 (6)
O3—C6	1.354 (4)	C10—C11	1.369 (5)
O3—H1O	0.8400	C11—C12	1.382 (5)
N1—C7	1.293 (4)	C12—C13	1.369 (5)
N1—C8	1.410 (4)	C2—H2	0.9500
N2—C11	1.471 (5)	C4—H4	0.9500
C1—C6	1.403 (5)	C5—H5	0.9500
C1—C7	1.448 (5)	C7—H7	0.9500
C1—C2	1.404 (5)	C10—H10	0.9500
C2—C3	1.365 (5)	C12—H12	0.9500
C3—C4	1.378 (7)	C13—H13	0.9500

C6—O3—H1O	109.00	N2—C11—C10	118.7 (3)
C7—N1—C8	120.9 (3)	C10—C11—C12	122.2 (3)
O1—N2—C11	117.1 (3)	N2—C11—C12	119.1 (3)
O2—N2—C11	118.7 (3)	C11—C12—C13	118.7 (3)
O1—N2—O2	124.2 (3)	C8—C13—C12	121.7 (3)
C2—C1—C7	118.8 (3)	F1—C14—F3	106.5 (3)
C6—C1—C7	122.8 (3)	F1—C14—C9	114.4 (3)
C2—C1—C6	118.5 (3)	F1—C14—F2	106.7 (3)
C1—C2—C3	120.3 (3)	F2—C14—C9	111.9 (3)
Br1—C3—C2	120.8 (3)	F3—C14—C9	111.3 (3)
Br1—C3—C4	118.0 (3)	F2—C14—F3	105.5 (3)
C2—C3—C4	121.2 (3)	C1—C2—H2	120.00
C3—C4—C5	119.6 (4)	C3—C2—H2	120.00
C4—C5—C6	120.1 (3)	C3—C4—H4	120.00
O3—C6—C5	118.1 (3)	C5—C4—H4	120.00
C1—C6—C5	120.3 (3)	C4—C5—H5	120.00
O3—C6—C1	121.6 (3)	C6—C5—H5	120.00
N1—C7—C1	120.8 (3)	N1—C7—H7	120.00
N1—C8—C13	125.4 (3)	C1—C7—H7	120.00
C9—C8—C13	117.9 (3)	C9—C10—H10	120.00
N1—C8—C9	116.7 (3)	C11—C10—H10	120.00
C8—C9—C14	120.1 (3)	C11—C12—H12	121.00
C10—C9—C14	119.8 (3)	C13—C12—H12	121.00
C8—C9—C10	120.1 (3)	C8—C13—H13	119.00
C9—C10—C11	119.3 (3)	C12—C13—H13	119.00

C8—N1—C7—C1	−178.1 (3)	C4—C5—C6—C1	−0.5 (6)
C7—N1—C8—C9	−177.4 (3)	N1—C8—C9—C10	−178.5 (3)
C7—N1—C8—C13	4.8 (5)	N1—C8—C9—C14	1.4 (5)
O1—N2—C11—C10	2.4 (4)	C13—C8—C9—C10	−0.5 (5)
O1—N2—C11—C12	−179.2 (3)	C13—C8—C9—C14	179.3 (3)
O2—N2—C11—C10	−175.8 (3)	N1—C8—C13—C12	178.3 (3)
O2—N2—C11—C12	2.5 (5)	C9—C8—C13—C12	0.5 (5)
C6—C1—C2—C3	0.3 (5)	C8—C9—C10—C11	0.7 (5)
C7—C1—C2—C3	−179.2 (3)	C14—C9—C10—C11	−179.2 (3)
C2—C1—C6—O3	−179.5 (3)	C8—C9—C14—F1	57.2 (4)
C2—C1—C6—C5	0.4 (5)	C8—C9—C14—F2	178.7 (3)
C7—C1—C6—O3	0.0 (6)	C8—C9—C14—F3	−63.6 (4)
C7—C1—C6—C5	179.9 (3)	C10—C9—C14—F1	−122.9 (3)
C2—C1—C7—N1	176.1 (3)	C10—C9—C14—F2	−1.5 (5)
C6—C1—C7—N1	−3.4 (5)	C10—C9—C14—F3	116.3 (4)
C1—C2—C3—Br1	179.2 (3)	C9—C10—C11—N2	177.4 (3)
C1—C2—C3—C4	−0.9 (5)	C9—C10—C11—C12	−0.8 (5)
Br1—C3—C4—C5	−179.3 (3)	N2—C11—C12—C13	−177.5 (3)
C2—C3—C4—C5	0.8 (6)	C10—C11—C12—C13	0.8 (5)
C3—C4—C5—C6	−0.1 (6)	C11—C12—C13—C8	−0.6 (5)
C4—C5—C6—O3	179.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O···N1	0.84	1.88	2.623 (4)	146
C10—H10···F2	0.95	2.35	2.685 (4)	100
C13—H13···O1ⁱ	0.95	2.50	3.134 (4)	125

Symmetry code: (i) x−1/2, −y−1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₈BrF₃N₂O₃
M_r	389.12
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	123
a, b, c (Å)	7.3596 (5), 16.4625 (10), 11.2599 (6)
β (°)	94.955 (5)
V (Å³)	1359.12 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	3.08
Crystal size (mm)	0.20 × 0.18 × 0.18

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.546, 0.575
No. of measured, independent and observed [I > 2σ(I)] reflections	6329, 3149, 2165
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.683

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.090, 1.02
No. of reflections	3149
No. of parameters	203
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.59

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1O···N1	0.84	1.88	2.623 (4)	146.

Acknowledgements

Manchester Metropolitan University, Erciyes University and the University of Strathclyde are gratefully acknowledged for supporting this study.

References

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