2-{[3-Chloro-4-(4-chloro­phen­oxy)phen­yl]imino­meth­yl}-4-nitro­phenol

Karadayı, N.; Köysal, Y.; Şahin, S.; Coşkun, E.; Büyükgüngör, O.

doi:10.1107/S1600536813012518

organic compounds

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ISSN: 2056-9890

Volume 69| Part 6| June 2013| Page o889

doi:10.1107/S1600536813012518

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2-{[3-Chloro-4-(4-chlorophenoxy)phenyl]iminomethyl}-4-nitrophenol

Nevzat Karadayı,^a ^* Yavuz Köysal,^a Songül Şahin,^b Emine Coşkun ^b and Orhan Büyükgüngör ^c

^aYeşilyurt Demir Celik Higher Vocational School, Ondokuz Mayıs University, TR-55300 Samsun, Turkey, ^bDepartment of Chemistry, Faculty of Arts and Sciences, Ondokuz Mayıs University, TR-55139 Samsun, Turkey, and ^cDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, TR-55139 Samsun, Turkey
^*Correspondence e-mail: nevzatk@omu.edu.tr

(Received 6 March 2013; accepted 7 May 2013; online 15 May 2013)

In the title compound, C₁₉H₁₂Cl₂N₂O₄, the imine bond length of 1.257 (6) Å is typical of a double bond. The dihedral angle between the para-nitro benzene ring and the central benzene ring is 12.06 (3)° and that between the central benzene and the para-chloro benzene ring is 73.81 (2)°. An intramolecular O—H⋯N hydrogen bond generates an S(6) ring motif. In the crystal, molecules are linked together by two pairs of C—H⋯O interactions (to the same O atom acceptor), forming inversion dimers. A short Cl⋯Cl contact [3.232 (4) Å] is observed.

Related literature

For applications of related Schiff base compounds, see: Santos et al. (2001 ); Cohen et al. (1964 ). For related structures, see: Aygün et al. (1998 ); Karadayı et al. (2003 , 2005 , 2006 ); Faridbod et al. (2008 ); Raja et al. (2008 ); Li & Zhang (2004 ); Köysal et al. (2012 ). For standard bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₉H₁₂Cl₂N₂O₄
M_r = 403.21
Triclinic, $[P \overline 1]$
a = 5.5649 (8) Å
b = 7.929 (1) Å
c = 21.778 (4) Å
α = 86.260 (12)°
β = 83.596 (12)°
γ = 70.739 (10)°
V = 901.1 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.39 mm⁻¹
T = 296 K
0.76 × 0.39 × 0.03 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.849, T_max = 0.985
10061 measured reflections
3475 independent reflections
1473 reflections with I > 2σ(I)
R_int = 0.076

Refinement

R[F² > 2σ(F²)] = 0.068
wR(F²) = 0.186
S = 1.05
3475 reflections
248 parameters
52 restraints
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.85	2.564 (5)	145
C7—H7⋯O3ⁱ	0.93	2.51	3.321 (6)	146
C6—H6⋯O3ⁱ	0.93	2.49	3.319 (4)	148
Symmetry code: (i) -x, -y+2, -z.

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, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813012518/rn2114sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813012518/rn2114Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813012518/rn2114Isup3.cml

checkCIF report

Comment top

Schiff base derivatives are found to exhibit important pharmacological properties, such as antibacterial, antitumor and antitoxic activities (Santos et al., 2001). Schiff base compounds can be classified by their photochromic and thermochromic characteristics (Cohen et al., 1964). In this study we report the structure of (I). The molecule structure of (I) is shown in Fig.1.

The N1=C7 bond length is 1.257 (6) Å, approximately equal to previously reported C=N double-bond lengths (Allen et al., 1987; Aygün et al., 1998; Karadayı et al., 2003; Faridbod et al., 2008). The geometric parameters in (I) are comparable with the similar reported structures (Raja et al., 2008; Li & Zhang, 2004; Karadayı et al., 2005; Karadayı et al., 2006; Köysal et al., 2012). The dihedral angles between the aromatic rings (C1—C6) and (C8—C13) is 12.06 (3)° and (C8—C13) and (C14—C19) is 73.81 (2)°.

The H atom is located on the hydroxy O atom rather than on the N atom. The molecular intramolecular O—H···N hydrogen bond result in formation of six-membered ring and generates an S(6) ring motif. The molecules in crystal are held together by two intermolecular C—H···O hydrogen bonds. (Table 1; Fig. 2).

Related literature top

For applications of related Schiff base compounds, see: Santos et al. (2001); Cohen et al. (1964). For related structures, see: Aygün et al. (1998); Karadayı et al. (2003, 2005, 2006); Faridbod et al. (2008); Raja et al. (2008); Li & Zhang (2004); Köysal et al. (2012). For standard bond lengths, see: Allen et al. (1987).

Experimental top

The compound 2-{[3-chloro-4-(4-chlorophenoxy)phenyl]carbonoimidoyl}-4-nitrophenol was prepared by reflux a mixture of a solution containing 2-hydroxy-5-nitrobenzaldehyde(0.014 g, 0.082 mmol) and a solution containing 3-Chloro-4-(4-chlorophenoxy)aniline(0,021 g, 0.082 mmol) in 20 ml e thanol. The reaction mixture was stirred for 1 h under reflux. The crystals of suitable for 2-{[3-chloro-4-(4-chlorophenoxy)phenyl]carbonoimidoyl}-4-nitrophenol X-ray analysis were obtained from ethylalcohol by slow evaporation (yield 58%). Mp: 436–438 K. Elemental analysis: Uv-vis (CHCl₃): λ=212 (A: 2,253), 242 (A: 2,186), 304 nm. (A: 1,019). IR (ν_max, cm^-1): 3090–3030(Ar—CH₂), 2840–2940 (CH₂), 2210 (CN), 1621, 1597, 1570, 1519, 1481, 1348, 1298, 1284, 1259, 1212, 1184, 1162, 1130, 1101, 1090, 1051, 1010, 976, 942, 927, 912, 870, 836, 823,780, 754, 725, 640, 598, 576, 546, 495.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); 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, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

	Fig. 1. An drawing of the title compound showing the atomic numbering scheme. Displacement ellipsoids of non-H atoms are shown at the 30% probability level.
	Fig. 2. A view of the hydrogen-bonding network in the title compound. Hydrogen bonds are indicated by dashed line.

2-{[3-Chloro-4-(4-chlorophenoxy)phenyl]iminomethyl}-4-nitrophenol top

Crystal data top

C₁₉H₁₂Cl₂N₂O₄	Z = 2
M_r = 403.21	F(000) = 412
Triclinic, P1	D_x = 1.486 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.5649 (8) Å	Cell parameters from 8340 reflections
b = 7.929 (1) Å	θ = 1.9–28.2°
c = 21.778 (4) Å	µ = 0.39 mm⁻¹
α = 86.260 (12)°	T = 296 K
β = 83.596 (12)°	Plate, yellow
γ = 70.739 (10)°	0.76 × 0.39 × 0.03 mm
V = 901.1 (2) Å³

Data collection top

Stoe IPDS 2 diffractometer	3475 independent reflections
Radiation source: fine-focus sealed tube	1473 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.076
ω scans	θ_max = 26.0°, θ_min = 1.9°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −6→6
T_min = 0.849, T_max = 0.985	k = −9→9
10061 measured reflections	l = −26→26

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.068	H-atom parameters constrained
wR(F²) = 0.186	w = 1/[σ²(F_o²) + (0.0634P)² + 0.1371P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
3475 reflections	Δρ_max = 0.20 e Å⁻³
248 parameters	Δρ_min = −0.22 e Å⁻³
52 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.011 (3)

Crystal data top

C₁₉H₁₂Cl₂N₂O₄	γ = 70.739 (10)°
M_r = 403.21	V = 901.1 (2) Å³
Triclinic, P1	Z = 2
a = 5.5649 (8) Å	Mo Kα radiation
b = 7.929 (1) Å	µ = 0.39 mm⁻¹
c = 21.778 (4) Å	T = 296 K
α = 86.260 (12)°	0.76 × 0.39 × 0.03 mm
β = 83.596 (12)°

Data collection top

Stoe IPDS 2 diffractometer	3475 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	1473 reflections with I > 2σ(I)
T_min = 0.849, T_max = 0.985	R_int = 0.076
10061 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	52 restraints
wR(F²) = 0.186	H-atom parameters constrained
S = 1.05	Δρ_max = 0.20 e Å⁻³
3475 reflections	Δρ_min = −0.22 e Å⁻³
248 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

	x	y	z	U_iso*/U_eq
Cl2	0.7962 (6)	−0.3765 (3)	0.45465 (11)	0.2198 (11)
Cl1	−0.0539 (2)	0.30360 (16)	0.22683 (8)	0.1373 (6)
C18	0.6896 (14)	−0.0931 (8)	0.3740 (3)	0.144 (2)
H18	0.8584	−0.1407	0.3573	0.173*
C17	0.6001 (16)	−0.1794 (9)	0.4229 (3)	0.156 (2)
C19	0.5349 (14)	0.0624 (8)	0.3493 (3)	0.142 (2)
H19	0.5998	0.1220	0.3168	0.171*
C16	0.3486 (18)	−0.1156 (11)	0.4467 (3)	0.177 (3)
H16	0.2860	−0.1763	0.4792	0.213*
O3	0.0233 (6)	1.2311 (4)	−0.04140 (18)	0.1345 (13)
C15	0.1920 (16)	0.0391 (11)	0.4217 (3)	0.161 (3)
H15	0.0222	0.0837	0.4379	0.193*
C14	0.2795 (15)	0.1313 (9)	0.3728 (3)	0.135 (2)
O2	0.2457 (6)	1.4083 (4)	−0.05235 (18)	0.1303 (13)
N2	0.1826 (7)	1.2896 (5)	−0.0236 (3)	0.1123 (14)
C10	0.1116 (9)	0.4319 (6)	0.2530 (3)	0.1125 (17)
C6	0.2397 (8)	1.0768 (5)	0.0639 (3)	0.1007 (16)
H6	0.1264	1.0298	0.0487	0.121*
C9	0.1661 (8)	0.5615 (5)	0.2153 (3)	0.1149 (17)
H9	0.1109	0.5833	0.1759	0.138*
C5	0.2973 (8)	1.2175 (5)	0.0331 (3)	0.1021 (16)
O4	0.1060 (9)	0.2799 (7)	0.3499 (2)	0.1582 (18)
C11	0.1866 (11)	0.3996 (7)	0.3121 (3)	0.129 (2)
C4	0.4639 (9)	1.2908 (6)	0.0547 (3)	0.1136 (18)
H4	0.5006	1.3863	0.0335	0.136*
C1	0.3481 (8)	1.0065 (5)	0.1168 (3)	0.0988 (15)
C7	0.2800 (9)	0.8626 (6)	0.1508 (3)	0.1049 (16)
H7	0.1647	0.8174	0.1355	0.126*
C8	0.3057 (8)	0.6620 (6)	0.2360 (3)	0.1062 (15)
C2	0.5222 (9)	1.0794 (6)	0.1393 (3)	0.1050 (15)
N1	0.3733 (7)	0.7978 (5)	0.2004 (2)	0.1090 (13)
C3	0.5729 (9)	1.2220 (7)	0.1071 (3)	0.1227 (19)
H3	0.6844	1.2715	0.1219	0.147*
O1	0.6321 (7)	1.0140 (5)	0.1906 (2)	0.1368 (13)
H1	0.6007	0.9221	0.2019	0.205*
C13	0.3831 (11)	0.6245 (7)	0.2947 (3)	0.1260 (18)
H13	0.4780	0.6887	0.3087	0.151*
C12	0.3265 (11)	0.4975 (8)	0.3331 (3)	0.147 (2)
H12	0.3801	0.4765	0.3727	0.177*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl2	0.339 (3)	0.1660 (17)	0.1594 (17)	−0.100 (2)	−0.0038 (18)	0.0157 (15)
Cl1	0.1270 (10)	0.1025 (8)	0.1993 (15)	−0.0557 (7)	−0.0076 (9)	−0.0410 (9)
C18	0.203 (6)	0.128 (4)	0.126 (5)	−0.095 (4)	0.022 (4)	−0.023 (4)
C17	0.258 (7)	0.142 (5)	0.100 (4)	−0.112 (5)	0.006 (5)	−0.019 (3)
C19	0.190 (6)	0.125 (4)	0.140 (5)	−0.098 (4)	0.020 (4)	−0.021 (4)
C16	0.273 (9)	0.182 (6)	0.103 (5)	−0.124 (6)	0.038 (5)	−0.013 (4)
O3	0.137 (2)	0.103 (2)	0.195 (4)	−0.068 (2)	−0.055 (2)	−0.010 (2)
C15	0.229 (7)	0.175 (5)	0.106 (5)	−0.113 (5)	0.033 (5)	−0.025 (4)
C14	0.196 (6)	0.123 (4)	0.120 (4)	−0.100 (4)	0.019 (5)	−0.037 (4)
O2	0.134 (3)	0.0930 (19)	0.184 (4)	−0.0598 (19)	−0.028 (2)	−0.004 (2)
N2	0.098 (3)	0.071 (2)	0.178 (4)	−0.037 (2)	−0.009 (3)	−0.032 (3)
C10	0.104 (3)	0.080 (3)	0.157 (5)	−0.032 (2)	0.000 (3)	−0.037 (3)
C6	0.081 (3)	0.069 (2)	0.160 (5)	−0.030 (2)	−0.014 (3)	−0.024 (3)
C9	0.106 (3)	0.080 (2)	0.164 (5)	−0.031 (2)	−0.016 (3)	−0.033 (3)
C5	0.081 (3)	0.070 (2)	0.161 (5)	−0.027 (2)	−0.008 (3)	−0.028 (3)
O4	0.169 (4)	0.153 (3)	0.178 (4)	−0.095 (3)	0.025 (3)	−0.029 (4)
C11	0.139 (4)	0.110 (4)	0.154 (5)	−0.065 (3)	0.017 (4)	−0.034 (4)
C4	0.095 (3)	0.086 (3)	0.177 (5)	−0.048 (3)	−0.018 (3)	−0.023 (3)
C1	0.079 (3)	0.066 (2)	0.157 (5)	−0.026 (2)	−0.013 (3)	−0.023 (3)
C7	0.090 (3)	0.077 (3)	0.153 (5)	−0.027 (2)	−0.017 (3)	−0.024 (3)
C8	0.104 (3)	0.079 (3)	0.139 (5)	−0.032 (2)	−0.009 (3)	−0.022 (3)
C2	0.085 (3)	0.086 (3)	0.151 (5)	−0.031 (2)	−0.027 (3)	−0.013 (3)
N1	0.103 (3)	0.080 (2)	0.153 (4)	−0.037 (2)	−0.015 (3)	−0.021 (3)
C3	0.098 (3)	0.106 (3)	0.186 (6)	−0.057 (3)	−0.024 (4)	−0.018 (4)
O1	0.120 (3)	0.124 (3)	0.191 (4)	−0.063 (2)	−0.045 (3)	−0.004 (3)
C13	0.145 (4)	0.111 (4)	0.143 (5)	−0.066 (3)	−0.016 (4)	−0.019 (4)
C12	0.189 (6)	0.141 (4)	0.143 (5)	−0.094 (5)	−0.009 (4)	−0.023 (4)

Geometric parameters (Å, º) top

Cl2—C17	1.735 (8)	C9—C8	1.405 (6)
Cl1—C10	1.737 (4)	C9—H9	0.9300
C18—C17	1.365 (8)	C5—C4	1.381 (6)
C18—C19	1.367 (8)	O4—C11	1.370 (7)
C18—H18	0.9300	C11—C12	1.394 (7)
C17—C16	1.374 (9)	C4—C3	1.350 (7)
C19—C14	1.394 (8)	C4—H4	0.9300
C19—H19	0.9300	C1—C2	1.424 (6)
C16—C15	1.370 (10)	C1—C7	1.452 (7)
C16—H16	0.9300	C7—N1	1.257 (6)
O3—N2	1.234 (4)	C7—H7	0.9300
C15—C14	1.386 (8)	C8—C13	1.377 (7)
C15—H15	0.9300	C8—N1	1.412 (6)
C14—O4	1.360 (8)	C2—O1	1.326 (6)
O2—N2	1.222 (5)	C2—C3	1.383 (7)
N2—C5	1.449 (6)	C3—H3	0.9300
C10—C9	1.365 (7)	O1—H1	0.8200
C10—C11	1.379 (8)	C13—C12	1.361 (7)
C6—C1	1.360 (6)	C13—H13	0.9300
C6—C5	1.375 (6)	C12—H12	0.9300
C6—H6	0.9300

C17—C18—C19	121.0 (7)	C4—C5—N2	119.3 (5)
C17—C18—H18	119.5	C14—O4—C11	120.2 (5)
C19—C18—H18	119.5	O4—C11—C10	118.5 (5)
C18—C17—C16	120.5 (8)	O4—C11—C12	121.8 (7)
C18—C17—Cl2	121.1 (7)	C10—C11—C12	119.5 (6)
C16—C17—Cl2	118.3 (6)	C3—C4—C5	119.2 (5)
C18—C19—C14	119.8 (6)	C3—C4—H4	120.4
C18—C19—H19	120.1	C5—C4—H4	120.4
C14—C19—H19	120.1	C6—C1—C2	119.3 (5)
C15—C16—C17	118.7 (7)	C6—C1—C7	120.2 (4)
C15—C16—H16	120.6	C2—C1—C7	120.5 (6)
C17—C16—H16	120.6	N1—C7—C1	121.4 (5)
C16—C15—C14	121.9 (8)	N1—C7—H7	119.3
C16—C15—H15	119.1	C1—C7—H7	119.3
C14—C15—H15	119.1	C13—C8—C9	117.8 (5)
O4—C14—C15	117.2 (7)	C13—C8—N1	117.9 (5)
O4—C14—C19	124.7 (6)	C9—C8—N1	124.3 (6)
C15—C14—C19	118.1 (8)	O1—C2—C3	120.2 (5)
O2—N2—O3	121.7 (5)	O1—C2—C1	121.0 (5)
O2—N2—C5	118.7 (4)	C3—C2—C1	118.7 (6)
O3—N2—C5	119.6 (4)	C7—N1—C8	123.2 (5)
C9—C10—C11	121.1 (5)	C4—C3—C2	121.4 (5)
C9—C10—Cl1	120.1 (5)	C4—C3—H3	119.3
C11—C10—Cl1	118.8 (5)	C2—C3—H3	119.3
C1—C6—C5	120.0 (4)	C2—O1—H1	109.5
C1—C6—H6	120.0	C12—C13—C8	122.8 (5)
C5—C6—H6	120.0	C12—C13—H13	118.6
C10—C9—C8	120.0 (6)	C8—C13—H13	118.6
C10—C9—H9	120.0	C13—C12—C11	118.8 (6)
C8—C9—H9	120.0	C13—C12—H12	120.6
C6—C5—C4	121.3 (6)	C11—C12—H12	120.6
C6—C5—N2	119.3 (4)

C14—C15—C16—C17	0.8 (11)	C16—C17—C18—C19	2.7 (9)
C15—C16—C17—C18	−2.0 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.85	2.564 (5)	145
C7—H7···O3ⁱ	0.93	2.51	3.321 (6)	146
C6—H6···O3ⁱ	0.93	2.49	3.319 (4)	148

Symmetry code: (i) −x, −y+2, −z.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₂Cl₂N₂O₄
M_r	403.21
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	5.5649 (8), 7.929 (1), 21.778 (4)
α, β, γ (°)	86.260 (12), 83.596 (12), 70.739 (10)
V (Å³)	901.1 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.39
Crystal size (mm)	0.76 × 0.39 × 0.03

Data collection
Diffractometer	Stoe IPDS 2 diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.849, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	10061, 3475, 1473
R_int	0.076
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.186, 1.05
No. of reflections	3475
No. of parameters	248
No. of restraints	52
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.22

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.85	2.564 (5)	145.2
C7—H7···O3ⁱ	0.93	2.51	3.321 (6)	146.1
C6—H6···O3ⁱ	0.93	2.49	3.319 (4)	148.4

Symmetry code: (i) −x, −y+2, −z.

Acknowledgements

The authors wish to acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund).

References

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