2-[(E)-(2-Morpholinoeth­yl)iminiometh­yl]-4-nitro-1-oxocyclo­hexa­dienide

Bingöl Alpaslan, Y.; Tanak, H.; Ağar, E.; Erşahin, F.

doi:10.1107/S1600536809026191

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1842

doi:10.1107/S1600536809026191

Open

access

2-[(E)-(2-Morpholinoethyl)iminiomethyl]-4-nitro-1-oxocyclohexadienide

Yelda Bingöl Alpaslan,^a Hasan Tanak,^a Erbil Ağar ^b and Ferda Erşahin ^b ^*

^aDepartment of Physics, Faculty of Arts & Science, Ondokuz Mayıs University, TR-55139 Kurupelit–Samsun, Turkey, and ^bDepartment of Chemistry, Faculty of Arts & Science, Ondokuz Mayıs University, 55139 Samsun, Turkey
^*Correspondence e-mail: ybingol@omu.edu.tr

(Received 28 June 2009; accepted 6 July 2009; online 11 July 2009)

The molecule of the title compound, C₁₃H₁₇N₃O₄, exists as a zwitterion, with the H atom of the phenol group being transferred to the imine N atom. The C=O, C_Ar—C_Ar and C—N bond lengths are in agreement with the oxocyclohexadienide–iminium zwitterionic form. A strong intramolecular N⁺—H⋯O hydrogen bond generates an S(6) ring motif. The morpholine ring adopts a chair conformation. In the crystal, molecules are linked into centrosymmetric dimers by intermolecular N—H⋯O hydrogen bonds. In addition, C—H⋯O hydrogen bonds and very weak C—H⋯π interactions are observed.

Related literature

For general background, photochromic and thermochromic characteristics of Schiff base compounds, see: Calligaris et al. (1972 ); Cohen et al. (1964 ); Hadjoudis et al. (1987 ); Karabıyık et al. (2008 ). For related structures, see: Butt et al. (1987 ); Petek et al. (2006 ); Krygowski & Stepien (2005 ); Santos-Contreras et al. (2009 ). For graph-set analysis of hydrogen bonds, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₃H₁₇N₃O₄
M_r = 279.30
Triclinic, $[P \overline 1]$
a = 5.3520 (4) Å
b = 10.8972 (9) Å
c = 12.4537 (9) Å
α = 102.329 (7)°
β = 97.143 (6)°
γ = 104.173 (9)°
V = 675.91 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.75 × 0.70 × 0.40 mm

Data collection

Stoe IPDSII diffractometer
Absorption correction: none
11340 measured reflections
3094 independent reflections
2664 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.110
S = 1.06
3094 reflections
186 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1⋯O1	0.89 (2)	1.99 (2)	2.6760 (14)	133 (2)
N2—H1⋯O1ⁱ	0.89 (2)	2.24 (2)	2.9587 (14)	138 (2)
C4—H4⋯O4ⁱⁱ	0.93	2.47	3.3547 (16)	160
C7—H7⋯O3ⁱⁱⁱ	0.93	2.43	3.3020 (15)	157
C13—H13B⋯Cg2^iv	0.97	2.99	3.9254	162
Symmetry codes: (i) -x, -y+1, -z+1; (ii) x, y+1, z+1; (iii) -x+2, -y+2, -z+1; (iv) -x+1, -y+1, -z+1. Cg2 is the centroid of the C1–C6 ring.

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809026191/ci2842sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809026191/ci2842Isup2.hkl

checkCIF report

Comment top

Schiff bases have been extensively used as ligands in the field of coordination chemistry (Calligaris et al., 1972). Schiff base compounds can be classified by their photochromic and thermochromic characteristics (Cohen et al. 1964). These properties result from proton transfer from the hydroxyl O atom to the imine N atom (Hadjoudis et al., 1987). Schiff bases exhibit two well-known tautomeric forms viz. OH and NH tautomers, and they also exist in zwitterionic form (Karabıyık et al., 2008). Our investigations show that compund (I) exists in a zwitterionic form.

The molecular structure of (I) is shown in Fig.1. The C1—C7 [1.4241 (15) Å], C7═N2 [1.2894 (15) Å] and N2—C8 [1.4615 (14) Å] bond lengths agree with the corresponding distances in (E)-2-methoxy-6-[(2- morpholinoethylimino)methyl]phenolate [1.425 (2), 1.287 (2) and 1.464 (2) Å; Petek et al., 2006]. The bonds lengths in the C1-C6 benzene ring show clear alternation in the delocalized C2-C5 portion. The nitro group is tilted out of the mean plane of adjacent ring by 7.02 (3)°, whereas the C3—N1 distance of 1.4398 (15) Å is in the characteristic range suggesting limited conjugation with the ring. Thus, the whole geometry is in the agreement with the predominace of the oxocyclohexadienide-iminum zwitterion bonding scheme (see scheme) (Krygowski & Stepien, 2005; Santos-Contreras et al., 2009), in close agreement with the reported configurations of p-nitrophenolates of alkali metal cations (Butt et al., 1987). The morpholine ring adopts a chair conformation. An intramolecular N—H···O hydrogen bond generates an S(6) ring motif (Bernstein et al., 1995).

In the crystal structure of (I), the molecules form centrosymmetric dimers connected by intermolecular N—H···O hydrogen bonds (Fig. 2). In addition, C—H···O hydrogen bonds and very weak C—H···π interactions between C13-H13B group and C1-C6 benzene ring are observed (Table 1).

Related literature top

For general background, photochromic and thermochromic characteristics of Schiff base compounds, see: Calligaris et al. (1972); Cohen et al. (1964); Hadjoudis et al. (1987); Karabıyık et al. (2008). For related structures, see: Butt et al. (1987); Petek et al. (2006); Krygowski & Stepien (2005); Santos-Contreras et al. (2009). For graph-set analysis of hydrogen bonds, see: Bernstein et al. (1995).

Experimental top

2-Hydroxy-5-nitrobenzaldehyde (0.0535 g, 0.32 mmol) in ethanol (20 ml) was added to 2-morpholinoethylamine (0.0417 g, 0.32 mmol) in ethanol (20 ml) and the reaction mixture was stirred for 1 h under reflux. Single crystals of the title compound suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution (yield % 65; m.p. 435-438 K).

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, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. A packing diagram for (I), showing O—H···O hydrogen-bonded (dashed lines) dimers. H atoms not involved in hydrogen bonding have been omitted for clarity.

2-[(E)-(2-morpholinoethyl)iminiomethyl]-4-nitro-1-oxocyclohexadienide top

Crystal data top

C₁₃H₁₇N₃O₄	Z = 2
M_r = 279.30	F(000) = 296
Triclinic, P1	D_x = 1.372 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.3520 (4) Å	Cell parameters from 23053 reflections
b = 10.8972 (9) Å	θ = 1.7–28.0°
c = 12.4537 (9) Å	µ = 0.10 mm⁻¹
α = 102.329 (7)°	T = 296 K
β = 97.143 (6)°	Prism, orange
γ = 104.173 (9)°	0.75 × 0.70 × 0.40 mm
V = 675.91 (10) Å³

Data collection top

Stoe IPDSII diffractometer	2664 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.039
Graphite monochromator	θ_max = 27.6°, θ_min = 1.7°
Detector resolution: 6.67 pixels mm^-1	h = −6→6
ω scans	k = −14→14
11340 measured reflections	l = −16→16
3094 independent 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)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.110	w = 1/[σ²(F_o²) + (0.0512P)² + 0.1309P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
3094 reflections	Δρ_max = 0.26 e Å⁻³
186 parameters	Δρ_min = −0.17 e Å⁻³
0 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: 0.077 (7)

Crystal data top

C₁₃H₁₇N₃O₄	γ = 104.173 (9)°
M_r = 279.30	V = 675.91 (10) Å³
Triclinic, P1	Z = 2
a = 5.3520 (4) Å	Mo Kα radiation
b = 10.8972 (9) Å	µ = 0.10 mm⁻¹
c = 12.4537 (9) Å	T = 296 K
α = 102.329 (7)°	0.75 × 0.70 × 0.40 mm
β = 97.143 (6)°

Data collection top

Stoe IPDSII diffractometer	2664 reflections with I > 2σ(I)
11340 measured reflections	R_int = 0.039
3094 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.26 e Å⁻³
3094 reflections	Δρ_min = −0.17 e Å⁻³
186 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.4611 (2)	0.77887 (11)	0.53094 (9)	0.0335 (2)
C2	0.6439 (2)	0.90243 (11)	0.56526 (9)	0.0341 (2)
H2	0.7896	0.9204	0.5315	0.041*
C3	0.6067 (2)	0.99713 (10)	0.64924 (9)	0.0348 (3)
C4	0.3899 (3)	0.97257 (12)	0.70256 (10)	0.0396 (3)
H4	0.3692	1.0377	0.7597	0.048*
C5	0.2112 (3)	0.85348 (12)	0.67033 (11)	0.0426 (3)
H5	0.0698	0.8382	0.7069	0.051*
C6	0.2318 (2)	0.74989 (11)	0.58183 (10)	0.0363 (3)
C7	0.5074 (2)	0.68324 (11)	0.44412 (9)	0.0358 (3)
H7	0.6566	0.7074	0.4138	0.043*
C8	0.4146 (3)	0.46932 (12)	0.31724 (10)	0.0430 (3)
H8A	0.3937	0.3878	0.3393	0.052*
H8B	0.5956	0.5004	0.3093	0.052*
C9	0.2370 (3)	0.44450 (12)	0.20590 (10)	0.0437 (3)
H9A	0.0572	0.4050	0.2113	0.052*
H9B	0.2453	0.5268	0.1865	0.052*
C10	0.2038 (3)	0.36092 (15)	0.00679 (11)	0.0513 (3)
H10A	0.2527	0.4500	−0.0009	0.062*
H10B	0.0140	0.3307	−0.0047	0.062*
C11	0.3025 (3)	0.27445 (17)	−0.07913 (12)	0.0640 (4)
H11A	0.2304	0.2783	−0.1534	0.077*
H11B	0.4920	0.3062	−0.0681	0.077*
C12	0.3364 (4)	0.13651 (16)	0.03730 (15)	0.0665 (5)
H12A	0.5264	0.1645	0.0487	0.080*
H12B	0.2834	0.0467	0.0429	0.080*
C13	0.2450 (3)	0.22200 (13)	0.12725 (12)	0.0504 (3)
H13A	0.0561	0.1904	0.1194	0.060*
H13B	0.3244	0.2177	0.2002	0.060*
N1	0.7884 (2)	1.12600 (10)	0.68031 (9)	0.0410 (3)
N2	0.3567 (2)	0.56554 (9)	0.40467 (8)	0.0378 (2)
N3	0.3171 (2)	0.35764 (10)	0.11888 (8)	0.0422 (3)
O1	0.06162 (19)	0.64042 (9)	0.55030 (9)	0.0513 (3)
O2	0.7384 (2)	1.21314 (9)	0.74731 (9)	0.0600 (3)
O3	0.9854 (2)	1.14568 (9)	0.63771 (9)	0.0549 (3)
O4	0.2302 (3)	0.14272 (12)	−0.07115 (9)	0.0727 (4)
H1	0.214 (4)	0.5433 (18)	0.4335 (15)	0.065 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0382 (6)	0.0302 (5)	0.0305 (5)	0.0089 (4)	0.0086 (4)	0.0041 (4)
C2	0.0370 (6)	0.0324 (5)	0.0316 (5)	0.0083 (4)	0.0096 (4)	0.0055 (4)
C3	0.0410 (6)	0.0286 (5)	0.0310 (5)	0.0073 (4)	0.0048 (4)	0.0035 (4)
C4	0.0493 (7)	0.0363 (6)	0.0335 (6)	0.0162 (5)	0.0120 (5)	0.0020 (4)
C5	0.0450 (7)	0.0419 (6)	0.0422 (6)	0.0125 (5)	0.0198 (5)	0.0065 (5)
C6	0.0388 (6)	0.0319 (5)	0.0372 (6)	0.0085 (4)	0.0102 (5)	0.0063 (4)
C7	0.0398 (6)	0.0336 (5)	0.0323 (5)	0.0088 (5)	0.0098 (4)	0.0049 (4)
C8	0.0508 (7)	0.0361 (6)	0.0374 (6)	0.0151 (5)	0.0086 (5)	−0.0038 (5)
C9	0.0545 (7)	0.0391 (6)	0.0375 (6)	0.0195 (5)	0.0105 (5)	0.0008 (5)
C10	0.0532 (8)	0.0582 (8)	0.0358 (7)	0.0119 (6)	0.0063 (6)	0.0030 (6)
C11	0.0646 (10)	0.0736 (10)	0.0367 (7)	0.0046 (8)	0.0132 (6)	−0.0071 (7)
C12	0.0776 (11)	0.0501 (8)	0.0648 (10)	0.0231 (8)	0.0203 (8)	−0.0105 (7)
C13	0.0625 (9)	0.0409 (7)	0.0457 (7)	0.0180 (6)	0.0147 (6)	−0.0003 (5)
N1	0.0491 (6)	0.0311 (5)	0.0371 (5)	0.0070 (4)	0.0045 (4)	0.0030 (4)
N2	0.0443 (6)	0.0317 (5)	0.0331 (5)	0.0083 (4)	0.0105 (4)	−0.0002 (4)
N3	0.0497 (6)	0.0406 (5)	0.0324 (5)	0.0146 (5)	0.0088 (4)	−0.0020 (4)
O1	0.0483 (5)	0.0358 (5)	0.0617 (6)	−0.0002 (4)	0.0219 (4)	0.0025 (4)
O2	0.0719 (7)	0.0337 (5)	0.0622 (6)	0.0106 (4)	0.0133 (5)	−0.0092 (4)
O3	0.0556 (6)	0.0417 (5)	0.0564 (6)	−0.0031 (4)	0.0169 (5)	0.0047 (4)
O4	0.0816 (8)	0.0612 (7)	0.0526 (6)	0.0055 (6)	0.0197 (6)	−0.0207 (5)

Geometric parameters (Å, º) top

C1—C2	1.3994 (16)	C9—H9A	0.97
C1—C7	1.4241 (15)	C9—H9B	0.97
C1—C6	1.4478 (16)	C10—N3	1.4625 (17)
C2—C3	1.3748 (15)	C10—C11	1.505 (2)
C2—H2	0.93	C10—H10A	0.97
C3—C4	1.4051 (17)	C10—H10B	0.97
C3—N1	1.4398 (15)	C11—O4	1.421 (2)
C4—C5	1.3543 (18)	C11—H11A	0.97
C4—H4	0.93	C11—H11B	0.97
C5—C6	1.4357 (16)	C12—O4	1.421 (2)
C5—H5	0.93	C12—C13	1.5086 (19)
C6—O1	1.2594 (14)	C12—H12A	0.97
C7—N2	1.2894 (15)	C12—H12B	0.97
C7—H7	0.93	C13—N3	1.4632 (18)
C8—N2	1.4615 (14)	C13—H13A	0.97
C8—C9	1.5117 (18)	C13—H13B	0.97
C8—H8A	0.97	N1—O2	1.2293 (14)
C8—H8B	0.97	N1—O3	1.2315 (14)
C9—N3	1.4596 (15)	N2—H1	0.887 (19)

C2—C1—C7	117.84 (10)	N3—C10—H10A	109.8
C2—C1—C6	120.88 (10)	C11—C10—H10A	109.8
C7—C1—C6	121.27 (10)	N3—C10—H10B	109.8
C3—C2—C1	119.54 (10)	C11—C10—H10B	109.8
C3—C2—H2	120.2	H10A—C10—H10B	108.2
C1—C2—H2	120.2	O4—C11—C10	111.17 (13)
C2—C3—C4	121.54 (10)	O4—C11—H11A	109.4
C2—C3—N1	119.24 (10)	C10—C11—H11A	109.4
C4—C3—N1	119.18 (10)	O4—C11—H11B	109.4
C5—C4—C3	119.65 (11)	C10—C11—H11B	109.4
C5—C4—H4	120.2	H11A—C11—H11B	108.0
C3—C4—H4	120.2	O4—C12—C13	111.48 (14)
C4—C5—C6	122.50 (11)	O4—C12—H12A	109.3
C4—C5—H5	118.8	C13—C12—H12A	109.3
C6—C5—H5	118.8	O4—C12—H12B	109.3
O1—C6—C5	122.23 (11)	C13—C12—H12B	109.3
O1—C6—C1	121.91 (10)	H12A—C12—H12B	108.0
C5—C6—C1	115.86 (10)	N3—C13—C12	110.35 (13)
N2—C7—C1	124.56 (11)	N3—C13—H13A	109.6
N2—C7—H7	117.7	C12—C13—H13A	109.6
C1—C7—H7	117.7	N3—C13—H13B	109.6
N2—C8—C9	111.99 (10)	C12—C13—H13B	109.6
N2—C8—H8A	109.2	H13A—C13—H13B	108.1
C9—C8—H8A	109.2	O2—N1—O3	122.35 (11)
N2—C8—H8B	109.2	O2—N1—C3	118.53 (11)
C9—C8—H8B	109.2	O3—N1—C3	119.11 (10)
H8A—C8—H8B	107.9	C7—N2—C8	122.84 (11)
N3—C9—C8	110.22 (10)	C7—N2—H1	117.3 (12)
N3—C9—H9A	109.6	C8—N2—H1	119.8 (12)
C8—C9—H9A	109.6	C9—N3—C10	111.82 (10)
N3—C9—H9B	109.6	C9—N3—C13	112.22 (10)
C8—C9—H9B	109.6	C10—N3—C13	108.56 (11)
H9A—C9—H9B	108.1	C12—O4—C11	109.63 (11)
N3—C10—C11	109.46 (13)

C7—C1—C2—C3	−179.68 (10)	N3—C10—C11—O4	60.36 (17)
C6—C1—C2—C3	0.69 (17)	O4—C12—C13—N3	−57.64 (18)
C1—C2—C3—C4	0.62 (18)	C2—C3—N1—O2	172.71 (11)
C1—C2—C3—N1	−176.92 (10)	C4—C3—N1—O2	−4.89 (17)
C2—C3—C4—C5	−0.61 (18)	C2—C3—N1—O3	−6.09 (17)
N1—C3—C4—C5	176.93 (11)	C4—C3—N1—O3	176.31 (11)
C3—C4—C5—C6	−0.7 (2)	C1—C7—N2—C8	−178.52 (11)
C4—C5—C6—O1	−178.16 (12)	C9—C8—N2—C7	−106.90 (14)
C4—C5—C6—C1	1.93 (19)	C8—C9—N3—C10	−163.51 (11)
C2—C1—C6—O1	178.21 (11)	C8—C9—N3—C13	74.22 (14)
C7—C1—C6—O1	−1.41 (18)	C11—C10—N3—C9	177.47 (12)
C2—C1—C6—C5	−1.89 (17)	C11—C10—N3—C13	−58.19 (15)
C7—C1—C6—C5	178.49 (11)	C12—C13—N3—C9	−178.84 (12)
C2—C1—C7—N2	179.62 (11)	C12—C13—N3—C10	57.05 (16)
C6—C1—C7—N2	−0.75 (18)	C13—C12—O4—C11	57.82 (18)
N2—C8—C9—N3	174.64 (11)	C10—C11—O4—C12	−59.34 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···O1	0.89 (2)	1.99 (2)	2.6760 (14)	133 (2)
N2—H1···O1ⁱ	0.89 (2)	2.24 (2)	2.9587 (14)	138 (2)
C4—H4···O4ⁱⁱ	0.93	2.47	3.3547 (16)	160
C7—H7···O3ⁱⁱⁱ	0.93	2.43	3.3020 (15)	157
C13—H13B···Cg2^iv	0.97	2.99	3.9254	162

Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, y+1, z+1; (iii) −x+2, −y+2, −z+1; (iv) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₇N₃O₄
M_r	279.30
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	5.3520 (4), 10.8972 (9), 12.4537 (9)
α, β, γ (°)	102.329 (7), 97.143 (6), 104.173 (9)
V (Å³)	675.91 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.75 × 0.70 × 0.40

Data collection
Diffractometer	Stoe IPDSII diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	11340, 3094, 2664
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.652

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.110, 1.06
No. of reflections	3094
No. of parameters	186
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.17

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···O1	0.89 (2)	1.99 (2)	2.6760 (14)	133 (2)
N2—H1···O1ⁱ	0.89 (2)	2.24 (2)	2.9587 (14)	138 (2)
C4—H4···O4ⁱⁱ	0.93	2.47	3.3547 (16)	160
C7—H7···O3ⁱⁱⁱ	0.93	2.43	3.3020 (15)	157
C13—H13B···Cg2^iv	0.97	2.9908	3.9254	162.14

Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, y+1, z+1; (iii) −x+2, −y+2, −z+1; (iv) −x+1, −y+1, −z+1.

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences of Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDSII diffractometer (purchased under grant No. F279 of the University Research Fund).

References

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
Butt, G. L., Mackay, M. F. & Topsom, R. D. (1987). Acta Cryst. C43, 1092–1094. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Calligaris, M., Nardin, G. & Randaccio, L. (1972). Coord. Chem. Rev. 7, 385–403. CrossRef CAS Web of Science Google Scholar
Cohen, M. D., Schmidt, G. M. J. & Flavian, S. (1964). J. Chem. Soc. pp. 2041–2051. CrossRef Web of Science 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
Hadjoudis, E., Vitterakis, M., Moustakali, I. & Mavridis, I. (1987). Tetrahedron, 43, 1345–1360. CrossRef CAS Web of Science Google Scholar
Karabıyık, H., Ocakİskeleli, N., Petek, H., Albayrak, Ç. & Ağar, E. (2008). J. Mol. Struct. 873, 130–136. Google Scholar
Krygowski, T. M. & Stepien, B. T. (2005). Chem. Rev. 105, 3482–3512. Web of Science CrossRef PubMed CAS Google Scholar
Petek, H., Albayrak, Ç., Ağar, E. & Kalkan, H. (2006). Acta Cryst. E62, o3685–o3687. Web of Science CSD CrossRef IUCr Journals Google Scholar
Santos-Contreras, R. J., Ramos-Organillo, A., García-Báez, E. V., Padilla-Martínez, I. I. & Martínez-Martínez, F. J. (2009). Acta Cryst. C65, o8–o10. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany. Google Scholar