(E)-3-[(2-Methyl-4-nitro­phen­yl)imino­meth­yl]-1-benzothio­phene

Inaç, H.; Dege, N.; Gümüş, S.; Ağar, E.; Soylu, M.S.

doi:10.1107/S1600536812000190

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o361

doi:10.1107/S1600536812000190

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(E)-3-[(2-Methyl-4-nitrophenyl)iminomethyl]-1-benzothiophene

Hasan Inaç,^a Necmi Dege,^b ^* Sümeyye Gümüş,^c Erbil Ağar ^c and Mustafa Serkan Soylu ^d

^aKırıkkale University, Faculty of Education, Department of Elementary Education, Science Teacher Training Programme, 71451 Kırıkkale, Turkey, ^bOndokuz Mayıs University, Arts and Sciences Faculty, Department of Physics, 55139 Samsun, Turkey, ^cOndokuz Mayıs University, Arts and Sciences Faculty, Department of Chemistry, 55139 Samsun, Turkey, and ^dGiresun University, Faculty of Arts and Sciences, Department of Physics, 28100 Giresun, Turkey
^*Correspondence e-mail: necmisamsun@gmail.com

(Received 29 December 2011; accepted 3 January 2012; online 11 January 2012)

In the title conpound, C₁₆H₁₂N₂O₂S, the 1-benzothiophene residue and the substituted benzene ring are oriented at a dihedral angle of 53.36 (6)°. The molecular conformation features a short C—H⋯N contact. There are no significant intermolecular contacts.

Related literature

For the biological activity of Schiff bases, see: Barton et al. (1979 ); Ingold (1969 ); Layer (1963 ). For industrial applications of Schiff bases, see: Taggi et al. (2002 ). For chemical properties of Schiff bases, see: Aydoğan et al. (2001 ). For related structures, see: Ağar et al. (2010 ); Ceylan et al. (2011 ); Dege et al. (2006 ); Demirtaş et al. (2009 ); Tecer et al. (2010 ).

Experimental

Crystal data

C₁₆H₁₂N₂O₂S
M_r = 296.34
Monoclinic, P 2₁
a = 7.6224 (4) Å
b = 7.9139 (4) Å
c = 11.7536 (5) Å
β = 91.341 (4)°
V = 708.82 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 296 K
0.17 × 0.15 × 0.12 mm

Data collection

Oxford Diffraction SuperNova Single source at offset diffractometer with an Eos detector
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.563, T_max = 1.000
2851 measured reflections
2108 independent reflections
1870 reflections with I > 2σ(I)
R_int = 0.013

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.089
S = 1.05
2108 reflections
191 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.14 e Å⁻³
Absolute structure: Flack (1983 ), 572 Friedel pairs
Flack parameter: −0.07 (11)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯N1	0.93	2.54	3.093 (4)	118

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: WinGX (Farrugia, 1997 ) and SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009 ) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: OLEX2, WinGX (Farrugia, 1999 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812000190/bt5774sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812000190/bt5774Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812000190/bt5774Isup3.cml

checkCIF report

Comment top

Schiff bases, i.e., compounds having a double C=N bond, are used as starting materials in the synthesis of important drugs, such as antibiotics and antiallergic, antiphlogistic, and antitumor substances (Barton et al., 1979; Layer, 1963; Ingold 1969). On the industrial scale, they have a wide range of applications, such as dyes and pigments (Taggi et al., 2002). Schiff bases have also been employed as ligands for the complexation of metal ions (Aydoğan et al., 2001).

The dihedral angle between the C10—C15 benzene and the C1—C9/S1 benzothiophene ring is 53.36 (6)°. The length of the C8=N1 double bond is 1.271 (3) Å, slightly shorter than standard 1.28 Å value of a C=N double bond and consistent with related structures (Ağar et al., 2010; Tecer et al., 2010; Ceylan et al. 2011; Demirtaş et al., 2009).

In the compound, N—O bond distances are 1.218 (4) Å for N2—O1 and N2—O2. The O1—N2—O2 bond angle is 123.4 (3)°. The C1—S1 and C9—S1 bond distances are 1.738 (3) Å and 1.709 (3) Å, respectively. The C—S bond distances are compatible with the literature (Dege et al. 2006; Demirtaş et al., 2009).

Related literature top

For the biological activity of Schiff bases, see: Barton et al. (1979); Ingold (1969); Layer (1963). For industrial applications of Schiff bases, see: Taggi et al. (2002). For chemical properties of Schiff bases, see: Aydoğan et al. (2001). For a related structure, see: Ağar et al. (2010); Ceylan et al. (2011); Dege et al. (2006); Demirtaş et al. (2009); Tecer et al. (2010).

Experimental top

The compound (E)-1-(1-benzothiophen-3-yl)-N-(2-methyl-4-nitrophenyl)methanimine was prepared by refluxing a mixture of a solution containing 1-benzothiophene-3-carbaldehyde (0.0102 g 0.063 mmol) in 20 ml ethanol and a solution containing 2-Methyl-4-nitroaniline (0.0095 g 0.063 mmol) in 20 ml ethanol. The reaction mixture was stirred for 1 h under reflux. The crystals of(E)-4-((benzo[b]thiophen-3-ylmethylene)amino)-3-methylbenzoic acid suitable for X-ray analysis were obtained from ethylalcohol by slow evaporation (yield = 63%; m.p: 153–155°C).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: WinGX (Farrugia, 1997) and SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

Fig. 1. The asymmetric unit of the title compound, showing the atomic numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

(E)-3-[(2-Methyl-4-nitrophenyl)iminomethyl]-1-benzothiophene top

Crystal data top

C₁₆H₁₂N₂O₂S	F(000) = 308
M_r = 296.34	D_x = 1.388 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: P 2yb	Cell parameters from 1356 reflections
a = 7.6224 (4) Å	θ = 3.2–27.7°
b = 7.9139 (4) Å	µ = 0.23 mm⁻¹
c = 11.7536 (5) Å	T = 296 K
β = 91.341 (4)°	Prism, brown
V = 708.82 (6) Å³	0.17 × 0.15 × 0.12 mm
Z = 2

Data collection top

Oxford Diffraction SuperNova Single source at offset diffractometer with an Eos detector	2108 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1870 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.013
Detector resolution: 16.0454 pixels mm^-1	θ_max = 27.8°, θ_min = 3.2°
ω scans	h = −4→9
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −10→5
T_min = 0.563, T_max = 1.000	l = −15→14
2851 measured reflections

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)] = 0.037	H-atom parameters constrained
wR(F²) = 0.089	w = 1/[σ²(F_o²) + (0.0369P)² + 0.1426P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2108 reflections	Δρ_max = 0.15 e Å⁻³
191 parameters	Δρ_min = −0.14 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 572 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.07 (11)

Crystal data top

C₁₆H₁₂N₂O₂S	V = 708.82 (6) Å³
M_r = 296.34	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 7.6224 (4) Å	µ = 0.23 mm⁻¹
b = 7.9139 (4) Å	T = 296 K
c = 11.7536 (5) Å	0.17 × 0.15 × 0.12 mm
β = 91.341 (4)°

Data collection top

Oxford Diffraction SuperNova Single source at offset diffractometer with an Eos detector	2108 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	1870 reflections with I > 2σ(I)
T_min = 0.563, T_max = 1.000	R_int = 0.013
2851 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.089	Δρ_max = 0.15 e Å⁻³
S = 1.05	Δρ_min = −0.14 e Å⁻³
2108 reflections	Absolute structure: Flack (1983), 572 Friedel pairs
191 parameters	Absolute structure parameter: −0.07 (11)
1 restraint

Special details top

Experimental. CrysAlis PRO (Oxford Diffraction, 2009)

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
C1	0.7745 (4)	0.7800 (4)	0.3597 (2)	0.0487 (7)
C2	0.9349 (4)	0.8478 (4)	0.3262 (3)	0.0621 (8)
H2	0.9650	0.8497	0.2500	0.075*
C3	1.0455 (4)	0.9109 (5)	0.4081 (3)	0.0662 (9)
H3	1.1529	0.9561	0.3876	0.079*
C4	0.9999 (4)	0.9087 (5)	0.5225 (3)	0.0591 (8)
H4	1.0768	0.9545	0.5768	0.071*
C5	0.8438 (4)	0.8401 (4)	0.5565 (2)	0.0491 (7)
H5	0.8165	0.8377	0.6332	0.059*
C6	0.7263 (4)	0.7740 (3)	0.4744 (2)	0.0444 (6)
C7	0.5540 (3)	0.6999 (5)	0.4864 (2)	0.0488 (6)
C8	0.4620 (3)	0.6719 (4)	0.5914 (2)	0.0512 (7)
H8	0.3469	0.6330	0.5868	0.061*
C9	0.4821 (4)	0.6556 (4)	0.3838 (2)	0.0585 (8)
H9	0.3708	0.6083	0.3759	0.070*
C10	0.4313 (3)	0.6683 (4)	0.7870 (2)	0.0497 (7)
C11	0.2601 (4)	0.7284 (4)	0.7959 (2)	0.0597 (8)
H11	0.2086	0.7888	0.7360	0.072*
C12	0.1660 (4)	0.6983 (5)	0.8939 (2)	0.0639 (8)
H12	0.0516	0.7373	0.9004	0.077*
C13	0.2467 (4)	0.6093 (4)	0.9806 (2)	0.0603 (9)
C14	0.4166 (4)	0.5529 (5)	0.9747 (2)	0.0614 (8)
H14	0.4677	0.4944	1.0355	0.074*
C15	0.5110 (4)	0.5831 (4)	0.8783 (2)	0.0539 (8)
C16	0.6974 (4)	0.5212 (6)	0.8702 (3)	0.0789 (11)
H16A	0.7464	0.5045	0.9453	0.118*
H16B	0.7657	0.6034	0.8307	0.118*
H16C	0.6986	0.4162	0.8293	0.118*
N1	0.5308 (3)	0.6980 (4)	0.68930 (16)	0.0527 (6)
N2	0.1479 (5)	0.5769 (5)	1.0843 (3)	0.0851 (10)
O1	0.2209 (5)	0.5011 (5)	1.1621 (2)	0.1246 (13)
O2	−0.0032 (4)	0.6264 (5)	1.0876 (2)	0.1153 (14)
S1	0.61283 (11)	0.69395 (13)	0.27057 (6)	0.0641 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0627 (17)	0.0399 (16)	0.0435 (14)	0.0049 (13)	0.0028 (12)	0.0020 (13)
C2	0.077 (2)	0.055 (2)	0.0559 (18)	−0.0021 (18)	0.0215 (15)	−0.0005 (16)
C3	0.0635 (19)	0.060 (2)	0.075 (2)	−0.0075 (17)	0.0136 (17)	0.0057 (18)
C4	0.0594 (17)	0.057 (2)	0.061 (2)	−0.0096 (16)	−0.0056 (15)	0.0006 (16)
C5	0.0591 (17)	0.0436 (16)	0.0445 (15)	−0.0019 (14)	−0.0013 (12)	0.0024 (14)
C6	0.0537 (15)	0.0366 (15)	0.0431 (14)	0.0046 (12)	0.0027 (11)	0.0028 (12)
C7	0.0583 (15)	0.0451 (16)	0.0430 (12)	−0.0049 (15)	−0.0015 (10)	0.0052 (16)
C8	0.0521 (14)	0.0483 (18)	0.0533 (15)	−0.0074 (15)	0.0006 (11)	0.0051 (16)
C9	0.0659 (18)	0.059 (2)	0.0505 (15)	−0.0105 (16)	−0.0039 (13)	0.0039 (15)
C10	0.0571 (15)	0.0471 (18)	0.0447 (13)	−0.0116 (15)	−0.0014 (11)	−0.0015 (14)
C11	0.0644 (18)	0.062 (2)	0.0524 (15)	−0.0003 (16)	−0.0018 (13)	0.0056 (16)
C12	0.0562 (16)	0.071 (2)	0.0654 (17)	−0.002 (2)	0.0102 (13)	−0.013 (2)
C13	0.074 (2)	0.067 (2)	0.0397 (15)	−0.0203 (16)	0.0091 (14)	−0.0096 (15)
C14	0.077 (2)	0.063 (2)	0.0440 (16)	−0.0119 (17)	−0.0038 (15)	−0.0017 (15)
C15	0.0631 (18)	0.058 (2)	0.0409 (15)	−0.0080 (14)	−0.0032 (13)	0.0020 (14)
C16	0.069 (2)	0.101 (3)	0.067 (2)	0.011 (2)	−0.0075 (17)	0.014 (2)
N1	0.0554 (12)	0.0593 (15)	0.0433 (11)	−0.0099 (15)	0.0006 (9)	0.0055 (15)
N2	0.100 (2)	0.103 (3)	0.0538 (18)	−0.034 (2)	0.0222 (17)	−0.0200 (18)
O1	0.149 (3)	0.169 (4)	0.0565 (16)	−0.017 (3)	0.0217 (17)	0.029 (2)
O2	0.096 (2)	0.175 (4)	0.0766 (17)	−0.027 (2)	0.0362 (15)	−0.0328 (19)
S1	0.0847 (5)	0.0675 (5)	0.0399 (3)	−0.0104 (5)	−0.0024 (3)	−0.0013 (4)

Geometric parameters (Å, º) top

C1—C2	1.401 (4)	C10—C11	1.395 (4)
C1—C6	1.406 (3)	C10—C15	1.395 (4)
C1—S1	1.738 (3)	C10—N1	1.411 (3)
C2—C3	1.359 (5)	C11—C12	1.391 (4)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.397 (5)	C12—C13	1.373 (5)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.376 (4)	C13—C14	1.373 (5)
C4—H4	0.9300	C13—N2	1.470 (4)
C5—C6	1.403 (4)	C14—C15	1.377 (4)
C5—H5	0.9300	C14—H14	0.9300
C6—C7	1.448 (4)	C15—C16	1.508 (4)
C7—C9	1.359 (3)	C16—H16A	0.9600
C7—C8	1.450 (3)	C16—H16B	0.9600
C8—N1	1.271 (3)	C16—H16C	0.9600
C8—H8	0.9300	N2—O1	1.218 (4)
C9—S1	1.709 (3)	N2—O2	1.218 (4)
C9—H9	0.9300

C2—C1—C6	122.1 (3)	C11—C10—N1	121.7 (3)
C2—C1—S1	126.3 (2)	C15—C10—N1	118.3 (3)
C6—C1—S1	111.6 (2)	C12—C11—C10	120.3 (3)
C3—C2—C1	118.3 (3)	C12—C11—H11	119.8
C3—C2—H2	120.9	C10—C11—H11	119.8
C1—C2—H2	120.9	C13—C12—C11	118.2 (3)
C2—C3—C4	120.8 (3)	C13—C12—H12	120.9
C2—C3—H3	119.6	C11—C12—H12	120.9
C4—C3—H3	119.6	C12—C13—C14	122.4 (3)
C5—C4—C3	121.4 (3)	C12—C13—N2	118.4 (3)
C5—C4—H4	119.3	C14—C13—N2	119.2 (3)
C3—C4—H4	119.3	C13—C14—C15	119.8 (3)
C4—C5—C6	119.3 (3)	C13—C14—H14	120.1
C4—C5—H5	120.3	C15—C14—H14	120.1
C6—C5—H5	120.3	C14—C15—C10	119.3 (3)
C5—C6—C1	118.1 (3)	C14—C15—C16	120.5 (3)
C5—C6—C7	130.5 (2)	C10—C15—C16	120.1 (3)
C1—C6—C7	111.4 (2)	C15—C16—H16A	109.5
C9—C7—C6	111.4 (2)	C15—C16—H16B	109.5
C9—C7—C8	121.5 (3)	H16A—C16—H16B	109.5
C6—C7—C8	127.0 (2)	C15—C16—H16C	109.5
N1—C8—C7	123.2 (2)	H16A—C16—H16C	109.5
N1—C8—H8	118.4	H16B—C16—H16C	109.5
C7—C8—H8	118.4	C8—N1—C10	119.4 (2)
C7—C9—S1	114.5 (2)	O1—N2—O2	123.4 (3)
C7—C9—H9	122.7	O1—N2—C13	118.3 (4)
S1—C9—H9	122.7	O2—N2—C13	118.3 (4)
C11—C10—C15	119.9 (2)	C9—S1—C1	91.03 (13)

C6—C1—C2—C3	−0.6 (5)	C10—C11—C12—C13	0.3 (5)
S1—C1—C2—C3	179.6 (3)	C11—C12—C13—C14	1.4 (5)
C1—C2—C3—C4	−0.3 (5)	C11—C12—C13—N2	−179.9 (3)
C2—C3—C4—C5	1.2 (5)	C12—C13—C14—C15	−1.0 (5)
C3—C4—C5—C6	−1.3 (5)	N2—C13—C14—C15	−179.7 (3)
C4—C5—C6—C1	0.3 (4)	C13—C14—C15—C10	−1.2 (5)
C4—C5—C6—C7	−178.2 (3)	C13—C14—C15—C16	−179.7 (3)
C2—C1—C6—C5	0.6 (4)	C11—C10—C15—C14	2.8 (5)
S1—C1—C6—C5	−179.6 (2)	N1—C10—C15—C14	179.9 (3)
C2—C1—C6—C7	179.4 (3)	C11—C10—C15—C16	−178.7 (3)
S1—C1—C6—C7	−0.8 (3)	N1—C10—C15—C16	−1.6 (5)
C5—C6—C7—C9	178.3 (3)	C7—C8—N1—C10	179.7 (3)
C1—C6—C7—C9	−0.3 (4)	C11—C10—N1—C8	−47.3 (5)
C5—C6—C7—C8	−1.9 (5)	C15—C10—N1—C8	135.7 (3)
C1—C6—C7—C8	179.5 (3)	C12—C13—N2—O1	−178.5 (3)
C9—C7—C8—N1	173.7 (3)	C14—C13—N2—O1	0.3 (5)
C6—C7—C8—N1	−6.1 (6)	C12—C13—N2—O2	1.9 (5)
C6—C7—C9—S1	1.3 (4)	C14—C13—N2—O2	−179.3 (3)
C8—C7—C9—S1	−178.5 (3)	C7—C9—S1—C1	−1.5 (3)
C15—C10—C11—C12	−2.4 (5)	C2—C1—S1—C9	−178.9 (3)
N1—C10—C11—C12	−179.4 (3)	C6—C1—S1—C9	1.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···N1	0.93	2.54	3.093 (4)	118

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂N₂O₂S
M_r	296.34
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	7.6224 (4), 7.9139 (4), 11.7536 (5)
β (°)	91.341 (4)
V (Å³)	708.82 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.17 × 0.15 × 0.12

Data collection
Diffractometer	Oxford Diffraction SuperNova Single source at offset diffractometer with an Eos detector
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.563, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	2851, 2108, 1870
R_int	0.013
(sin θ/λ)_max (Å⁻¹)	0.655

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.089, 1.05
No. of reflections	2108
No. of parameters	191
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.14
Absolute structure	Flack (1983), 572 Friedel pairs
Absolute structure parameter	−0.07 (11)

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), WinGX (Farrugia, 1997) and SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009) and ORTEP-3 for Windows (Farrugia, 1997), OLEX2 (Dolomanov et al., 2009), 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
C5—H5···N1	0.93	2.54	3.093 (4)	118.2

Acknowledgements

The authors thank Ondokuz Mayis University and the Giresun University Research Fund for financial support of this study.

References

Ağar, A., Tanak, H. & Yavuz, M. (2010). Mol. Phys. 108, 1759–1772. Google Scholar
Aydoğan, F., Öcal, N., Turgut, Z. & Yolaçan, C. (2001). Bull. Korean Chem. Soc. 22, 476–480. CAS Google Scholar
Barton, D. & Ollis, W. D. (1979). Comprehensive Organic Chemistry, Vol. 2. Oxford: Pergamon. Google Scholar
Ceylan, Ü., Tanak, H., Gümüş, S. & Ağar, E. (2011). Acta Cryst. E67, o2004. Web of Science CSD CrossRef IUCr Journals Google Scholar
Dege, N., Şekerci, M., Servi, S., Dinçer, M. & Demirbaş, Ü. (2006). Turk. J. Chem. 30, 103–108. CAS Google Scholar
Demirtaş, G., Dege, N., Şekerci, M., Servi, S. & Dinçer, M. (2009). Acta Cryst. E65, o1668. Web of Science CSD CrossRef IUCr Journals Google Scholar
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Ingold, C. K. (1969). In Structure and Mechanism in Organic Chemistry, 2nd ed. Ithaca, New York: Cornell University Press. Google Scholar
Layer, R. W. (1963). Chem. Rev. 63, 489–510. CrossRef CAS Web of Science Google Scholar
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Taggi, A. E., Hafez, A. M., Wack, H., Young, B., Ferraris, D. & Lectka, T. (2002). J. Am. Chem. Soc. 124, 6626–6635. Web of Science CrossRef PubMed CAS Google Scholar
Tecer, E., Dege, N., Zülfikaroğlu, A., Şenyüz, N. & Batı, H. (2010). Acta Cryst. E66, o3369–o3370. Web of Science CSD CrossRef IUCr Journals Google Scholar