2-[(E)-2-(4-Methyl­benzene­sulfonamido)ethyl­iminiometh­yl]-4-nitro­phenolate

Tüfekçi, M.; Alpaslan, G.; Macit, M.; Erdönmez, A.

doi:10.1107/S1600536809031481

organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2143

doi:10.1107/S1600536809031481

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2-[(E)-2-(4-Methylbenzenesulfonamido)ethyliminiomethyl]-4-nitrophenolate

Marife Tüfekçi,^a Gökhan Alpaslan,^a ^* Mustafa Macit ^b and Ahmet Erdönmez ^a

^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: gokhana@omu.edu.tr

(Received 7 August 2009; accepted 10 August 2009; online 15 August 2009)

The molecule of the title compound, C₁₆H₁₇N₃O₅S, crystallizes in a zwitterionic form, with a strong intramolecular N—H⋯O hydrogen bond. The dihedral angle between the two benzene rings is 7.06 (9)°. In the crystal, molecules are linked into chains along the c axis by intermolecular N—H⋯O hydrogen bonds.

Related literature

For general background to Schiff bases, see: Calligaris et al. (1972 ); Cohen et al. (1964 ); Hadjoudis et al. (1987 ); Karabıyık et al. (2008 ). For the crystal structure of 2-[2-(1H-indol-3-yl)ethyliminiomethyl]-4-nitrophenolate, see: Ali et al. (2008 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₆H₁₇N₃O₅S
M_r = 363.39
Monoclinic, P 2₁ /c
a = 17.915 (5) Å
b = 7.342 (5) Å
c = 13.055 (5) Å
β = 103.928 (5)°
V = 1666.7 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 296 K
0.68 × 0.50 × 0.26 mm

Data collection

Stoe IPDS-II diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.887, T_max = 0.956
22908 measured reflections
3272 independent reflections
2845 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.094
S = 1.07
3272 reflections
236 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H1⋯O3ⁱ	0.78 (2)	2.06 (2)	2.833 (2)	170 (2)
N2—H1A⋯O3	0.87 (2)	1.94 (2)	2.648 (2)	137 (2)
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32; 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/S1600536809031481/ci2882sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809031481/ci2882Isup2.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 a 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 the title compund has a zwitterionic form with a strong intramolecular N—H···O hydrogen bond (Fig. 1).

The C7N2 [1.292 (2) Å] and C6—03 [1.272 (2) Å] bond distances in the title compound are comparable to those [1.292 (2) and 1.264 (2) Å] observed in a related zwitterionic structure (Ali et al., 2008). The molecule adopts a folded conformation. The dihedral angle between the two benzene rings is 7.06 (9)°.

The intramolecular N2—H1A···O3 hydrogen bond generates an S(6) ring motif (Bernstein et al., 1995). The molecules are linked into chains (Fig. 2) along the c axis by intermolecular N—H···O hydrogen bonds (Table 1).

Related literature top

For general background to Schiff bases, see: Calligaris et al. (1972); Cohen et al. (1964); Hadjoudis et al. (1987); Karabıyık et al. (2008). For the crystal structure of 2-[2-(1H-indol-3-yl)ethyliminiomethyl]-4-nitrophenolate, see: Ali et al. (2008). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

2-Hydroxy-5-nitrobenzaldehyde (10 mg, 5.98× 10^-2 mmol) in ethanol (20 ml) was added to a solution of N-p-tolyl-sulfonylethylenediamine (12.7 mg, 5.98× 10^-2 mmol) in ethanol (20 ml). The reaction mixture was stirred for 1 h under reflux. Single crystals of the title compound were obtained by slow evaporation of an ethylacetate solution (yield 55%; m.p. 446–447 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 30% probability level and H atoms are shown as small spheres of arbitrary radii. The dashed line indicates a hydrogen bond.
	Fig. 2. A packing diagram for (I). H atoms not involved in hydrogen bonding (dashed lines) have been omitted for clarity.

2-[(E)-2-(4-Methylbenzenesulfonamido)ethyliminiomethyl]-4-nitrophenolate top

Crystal data top

C₁₆H₁₇N₃O₅S	F(000) = 760
M_r = 363.39	D_x = 1.448 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 37649 reflections
a = 17.915 (5) Å	θ = 1.6–28.0°
b = 7.342 (5) Å	µ = 0.23 mm⁻¹
c = 13.055 (5) Å	T = 296 K
β = 103.928 (5)°	Block, yellow
V = 1666.7 (14) Å³	0.68 × 0.50 × 0.26 mm
Z = 4

Data collection top

Stoe IPDS-II diffractometer	3272 independent reflections
Radiation source: fine-focus sealed tube	2845 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.0°, θ_min = 2.3°
ω scans	h = −22→22
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −9→9
T_min = 0.887, T_max = 0.956	l = −16→15
22908 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)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.094	w = 1/[σ²(F_o²) + (0.0542P)² + 0.2378P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.004
3272 reflections	Δρ_max = 0.26 e Å⁻³
236 parameters	Δρ_min = −0.27 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: 0.0025 (8)

Crystal data top

C₁₆H₁₇N₃O₅S	V = 1666.7 (14) Å³
M_r = 363.39	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.915 (5) Å	µ = 0.23 mm⁻¹
b = 7.342 (5) Å	T = 296 K
c = 13.055 (5) Å	0.68 × 0.50 × 0.26 mm
β = 103.928 (5)°

Data collection top

Stoe IPDS-II diffractometer	3272 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	2845 reflections with I > 2σ(I)
T_min = 0.887, T_max = 0.956	R_int = 0.024
22908 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.26 e Å⁻³
3272 reflections	Δρ_min = −0.27 e Å⁻³
236 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
C1	0.73857 (9)	0.1439 (2)	0.58535 (12)	0.0464 (3)
C2	0.81399 (10)	0.1345 (2)	0.64584 (14)	0.0559 (4)
H2	0.8238	0.1405	0.7190	0.067*
C3	0.87338 (10)	0.1163 (3)	0.59823 (15)	0.0604 (4)
C4	0.86008 (11)	0.1075 (3)	0.48830 (16)	0.0648 (5)
H4	0.9012	0.0958	0.4567	0.078*
C5	0.78743 (11)	0.1160 (3)	0.42812 (15)	0.0642 (5)
H5	0.7796	0.1093	0.3552	0.077*
C6	0.72214 (10)	0.1346 (2)	0.47198 (13)	0.0523 (4)
C7	0.67882 (9)	0.1617 (2)	0.63841 (13)	0.0463 (3)
H7	0.6925	0.1648	0.7118	0.056*
C8	0.54749 (9)	0.1973 (2)	0.65034 (13)	0.0466 (4)
H8A	0.5661	0.1505	0.7214	0.056*
H8B	0.5024	0.1275	0.6162	0.056*
C9	0.52559 (8)	0.3947 (2)	0.65549 (12)	0.0438 (3)
H9A	0.5085	0.4419	0.5843	0.053*
H9B	0.4829	0.4035	0.6889	0.053*
C10	0.69671 (8)	0.65737 (19)	0.62312 (11)	0.0400 (3)
C11	0.69016 (9)	0.6244 (2)	0.51721 (12)	0.0495 (4)
H11	0.6420	0.6182	0.4705	0.059*
C12	0.75608 (10)	0.6008 (3)	0.48147 (13)	0.0571 (4)
H12	0.7515	0.5781	0.4102	0.068*
C13	0.82838 (10)	0.6100 (2)	0.54833 (15)	0.0553 (4)
C14	0.83365 (10)	0.6421 (3)	0.65479 (15)	0.0601 (4)
H14	0.8818	0.6474	0.7015	0.072*
C15	0.76879 (9)	0.6661 (2)	0.69225 (13)	0.0522 (4)
H15	0.7733	0.6882	0.7636	0.063*
C16	0.89969 (12)	0.5917 (3)	0.50703 (19)	0.0795 (6)
H16A	0.8863	0.5403	0.4374	0.119*
H16B	0.9359	0.5136	0.5529	0.119*
H16C	0.9223	0.7097	0.5045	0.119*
N1	0.95110 (10)	0.1062 (3)	0.66326 (18)	0.0917 (6)
N2	0.60663 (7)	0.17413 (18)	0.59235 (11)	0.0456 (3)
N3	0.58876 (7)	0.50612 (18)	0.71366 (10)	0.0448 (3)
O1	0.96069 (10)	0.1084 (5)	0.75840 (16)	0.1571 (12)
O2	1.00420 (9)	0.0954 (4)	0.62016 (16)	0.1183 (7)
O3	0.65360 (7)	0.1427 (2)	0.41569 (9)	0.0669 (4)
O4	0.55334 (6)	0.75149 (15)	0.58460 (9)	0.0479 (3)
O5	0.63776 (6)	0.81294 (15)	0.76080 (9)	0.0522 (3)
S1	0.614192 (19)	0.69488 (5)	0.67146 (3)	0.03887 (13)
H1	0.6088 (10)	0.478 (2)	0.7710 (14)	0.048 (5)*
H1A	0.5970 (12)	0.176 (3)	0.5235 (17)	0.067 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0470 (8)	0.0456 (8)	0.0471 (8)	−0.0002 (6)	0.0121 (7)	−0.0028 (7)
C2	0.0522 (9)	0.0660 (10)	0.0494 (9)	−0.0005 (8)	0.0124 (7)	0.0003 (8)
C3	0.0452 (9)	0.0709 (11)	0.0658 (11)	0.0025 (8)	0.0148 (8)	0.0017 (9)
C4	0.0601 (11)	0.0720 (12)	0.0701 (12)	0.0056 (9)	0.0307 (9)	−0.0012 (10)
C5	0.0709 (12)	0.0753 (12)	0.0507 (9)	0.0086 (10)	0.0232 (9)	−0.0062 (9)
C6	0.0568 (10)	0.0516 (9)	0.0487 (9)	0.0038 (7)	0.0130 (7)	−0.0072 (7)
C7	0.0505 (9)	0.0449 (8)	0.0432 (8)	−0.0021 (6)	0.0107 (7)	−0.0007 (6)
C8	0.0438 (8)	0.0475 (8)	0.0502 (9)	−0.0058 (6)	0.0147 (7)	0.0030 (7)
C9	0.0348 (7)	0.0498 (8)	0.0472 (8)	−0.0037 (6)	0.0109 (6)	0.0008 (7)
C10	0.0389 (7)	0.0409 (7)	0.0399 (7)	−0.0016 (6)	0.0089 (6)	0.0033 (6)
C11	0.0425 (8)	0.0643 (10)	0.0407 (8)	−0.0008 (7)	0.0079 (6)	0.0049 (7)
C12	0.0556 (10)	0.0750 (12)	0.0440 (9)	0.0037 (8)	0.0185 (7)	0.0086 (8)
C13	0.0469 (9)	0.0583 (10)	0.0651 (11)	0.0003 (7)	0.0222 (8)	0.0094 (8)
C14	0.0378 (8)	0.0749 (12)	0.0637 (11)	−0.0013 (8)	0.0044 (7)	0.0005 (9)
C15	0.0444 (8)	0.0643 (10)	0.0450 (8)	0.0001 (7)	0.0054 (7)	−0.0027 (7)
C16	0.0553 (11)	0.0987 (16)	0.0943 (15)	0.0034 (11)	0.0372 (11)	0.0117 (13)
N1	0.0490 (9)	0.1412 (19)	0.0847 (13)	0.0029 (11)	0.0154 (9)	0.0064 (13)
N2	0.0471 (7)	0.0463 (7)	0.0444 (7)	−0.0015 (5)	0.0131 (6)	−0.0026 (6)
N3	0.0466 (7)	0.0521 (8)	0.0328 (7)	−0.0071 (6)	0.0041 (5)	0.0045 (6)
O1	0.0575 (10)	0.327 (4)	0.0791 (12)	0.0105 (15)	0.0021 (9)	0.0096 (18)
O2	0.0494 (8)	0.195 (2)	0.1165 (14)	0.0089 (11)	0.0310 (9)	−0.0005 (14)
O3	0.0600 (8)	0.0888 (9)	0.0472 (7)	0.0093 (7)	0.0038 (6)	−0.0159 (6)
O4	0.0417 (5)	0.0488 (6)	0.0494 (6)	0.0043 (4)	0.0034 (5)	0.0055 (5)
O5	0.0512 (6)	0.0543 (6)	0.0504 (6)	−0.0036 (5)	0.0108 (5)	−0.0159 (5)
S1	0.03696 (19)	0.0403 (2)	0.0382 (2)	0.00009 (14)	0.00693 (14)	−0.00238 (14)

Geometric parameters (Å, º) top

C1—C2	1.393 (2)	C10—C15	1.387 (2)
C1—C7	1.414 (2)	C10—S1	1.7631 (15)
C1—C6	1.440 (2)	C11—C12	1.381 (2)
C2—C3	1.362 (2)	C11—H11	0.93
C2—H2	0.93	C12—C13	1.378 (3)
C3—C4	1.399 (3)	C12—H12	0.93
C3—N1	1.448 (3)	C13—C14	1.390 (3)
C4—C5	1.350 (3)	C13—C16	1.507 (2)
C4—H4	0.93	C14—C15	1.376 (2)
C5—C6	1.427 (2)	C14—H14	0.93
C5—H5	0.93	C15—H15	0.93
C6—O3	1.272 (2)	C16—H16A	0.96
C7—N2	1.292 (2)	C16—H16B	0.96
C7—H7	0.93	C16—H16C	0.96
C8—N2	1.4529 (19)	N1—O1	1.212 (3)
C8—C9	1.507 (2)	N1—O2	1.219 (2)
C8—H8A	0.97	N2—H1A	0.87 (2)
C8—H8B	0.97	N3—S1	1.5976 (16)
C9—N3	1.4537 (19)	N3—H1	0.777 (18)
C9—H9A	0.97	O4—S1	1.4325 (11)
C9—H9B	0.97	O5—S1	1.4329 (12)
C10—C11	1.381 (2)

C2—C1—C7	118.18 (15)	C10—C11—C12	119.13 (15)
C2—C1—C6	120.72 (15)	C10—C11—H11	120.4
C7—C1—C6	121.10 (15)	C12—C11—H11	120.4
C3—C2—C1	120.26 (16)	C13—C12—C11	121.97 (16)
C3—C2—H2	119.9	C13—C12—H12	119.0
C1—C2—H2	119.9	C11—C12—H12	119.0
C2—C3—C4	120.93 (17)	C12—C13—C14	117.95 (15)
C2—C3—N1	118.96 (18)	C12—C13—C16	121.15 (18)
C4—C3—N1	120.11 (17)	C14—C13—C16	120.87 (17)
C5—C4—C3	119.81 (16)	C15—C14—C13	121.12 (16)
C5—C4—H4	120.1	C15—C14—H14	119.4
C3—C4—H4	120.1	C13—C14—H14	119.4
C4—C5—C6	122.64 (17)	C14—C15—C10	119.75 (16)
C4—C5—H5	118.7	C14—C15—H15	120.1
C6—C5—H5	118.7	C10—C15—H15	120.1
O3—C6—C5	122.91 (16)	C13—C16—H16A	109.5
O3—C6—C1	121.46 (15)	C13—C16—H16B	109.5
C5—C6—C1	115.63 (16)	H16A—C16—H16B	109.5
N2—C7—C1	124.73 (15)	C13—C16—H16C	109.5
N2—C7—H7	117.6	H16A—C16—H16C	109.5
C1—C7—H7	117.6	H16B—C16—H16C	109.5
N2—C8—C9	111.47 (12)	O1—N1—O2	122.7 (2)
N2—C8—H8A	109.3	O1—N1—C3	118.65 (18)
C9—C8—H8A	109.3	O2—N1—C3	118.7 (2)
N2—C8—H8B	109.3	C7—N2—C8	122.67 (14)
C9—C8—H8B	109.3	C7—N2—H1A	114.1 (14)
H8A—C8—H8B	108.0	C8—N2—H1A	123.0 (14)
N3—C9—C8	112.72 (13)	C9—N3—S1	123.98 (11)
N3—C9—H9A	109.0	C9—N3—H1	118.3 (13)
C8—C9—H9A	109.0	S1—N3—H1	117.4 (13)
N3—C9—H9B	109.0	O4—S1—O5	119.20 (8)
C8—C9—H9B	109.0	O4—S1—N3	107.39 (7)
H9A—C9—H9B	107.8	O5—S1—N3	107.26 (8)
C11—C10—C15	120.07 (14)	O4—S1—C10	107.82 (7)
C11—C10—S1	120.62 (11)	O5—S1—C10	106.12 (7)
C15—C10—S1	119.29 (12)	N3—S1—C10	108.74 (7)

C7—C1—C2—C3	179.67 (16)	C12—C13—C14—C15	−0.7 (3)
C6—C1—C2—C3	0.0 (3)	C16—C13—C14—C15	177.35 (18)
C1—C2—C3—C4	0.2 (3)	C13—C14—C15—C10	0.3 (3)
C1—C2—C3—N1	−179.76 (18)	C11—C10—C15—C14	0.1 (3)
C2—C3—C4—C5	−0.4 (3)	S1—C10—C15—C14	−178.20 (13)
N1—C3—C4—C5	179.6 (2)	C2—C3—N1—O1	2.3 (4)
C3—C4—C5—C6	0.3 (3)	C4—C3—N1—O1	−177.7 (3)
C4—C5—C6—O3	180.00 (19)	C2—C3—N1—O2	−177.8 (2)
C4—C5—C6—C1	0.0 (3)	C4—C3—N1—O2	2.2 (4)
C2—C1—C6—O3	179.83 (16)	C1—C7—N2—C8	−178.27 (14)
C7—C1—C6—O3	0.2 (3)	C9—C8—N2—C7	96.71 (17)
C2—C1—C6—C5	−0.1 (2)	C8—C9—N3—S1	131.22 (13)
C7—C1—C6—C5	−179.75 (16)	C9—N3—S1—O4	14.65 (14)
C2—C1—C7—N2	179.17 (15)	C9—N3—S1—O5	143.88 (12)
C6—C1—C7—N2	−1.2 (3)	C9—N3—S1—C10	−101.76 (13)
N2—C8—C9—N3	−63.94 (17)	C11—C10—S1—O4	−21.41 (15)
C15—C10—C11—C12	−0.1 (2)	C15—C10—S1—O4	156.87 (13)
S1—C10—C11—C12	178.14 (13)	C11—C10—S1—O5	−150.18 (13)
C10—C11—C12—C13	−0.3 (3)	C15—C10—S1—O5	28.09 (15)
C11—C12—C13—C14	0.7 (3)	C11—C10—S1—N3	94.72 (14)
C11—C12—C13—C16	−177.38 (18)	C15—C10—S1—N3	−87.00 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1···O3ⁱ	0.78 (2)	2.06 (2)	2.833 (2)	170 (2)
N2—H1A···O3	0.87 (2)	1.94 (2)	2.648 (2)	137 (2)

Symmetry code: (i) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₇N₃O₅S
M_r	363.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	17.915 (5), 7.342 (5), 13.055 (5)
β (°)	103.928 (5)
V (Å³)	1666.7 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.68 × 0.50 × 0.26

Data collection
Diffractometer	Stoe IPDS-II diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.887, 0.956
No. of measured, independent and observed [I > 2σ(I)] reflections	22908, 3272, 2845
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.094, 1.07
No. of reflections	3272
No. of parameters	236
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.27

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
N3—H1···O3ⁱ	0.78 (2)	2.06 (2)	2.833 (2)	170 (2)
N2—H1A···O3	0.87 (2)	1.94 (2)	2.648 (2)	137 (2)

Symmetry code: (i) x, −y+1/2, z+1/2.

Acknowledgements

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

References

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