Dimethyl trans-3-(4-bromo­phen­yl)-2-methyl­isoxazolidine-4,5-dicarboxyl­ate

Büyükgüngör, O.; Yavuz, S.; Odabaşoğlu, M.; Özkan, H.; Pamir, Ö.; Yıldırır, Y.

doi:10.1107/S1600536809032462

organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2207

doi:10.1107/S1600536809032462

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Dimethyl trans-3-(4-bromophenyl)-2-methylisoxazolidine-4,5-dicarboxylate

Orhan Büyükgüngör,^a ^* Serkan Yavuz,^b Mustafa Odabaşoğlu,^c Hamdi Özkan,^d Özgür Pamir ^b and Yılmaz Yıldırır ^b

^aDepartment of Physics, Faculty of Arts & Science, Ondokuz Mayıs University, TR-55139 Kurupelit Samsun, Turkey, ^bDepartment of Chemistry, Faculty of Arts & Science, Gazi University, Ankara, Turkey, ^cChemical Technology Program, Denizli Higher Vocational School, Pamukkale University, TR-20159 Kınıklı, Denizli, Turkey, and ^dDepartment of Chemistry, Faculty of Arts & Science, Kırıkkale University, Kırıkkale, Turkey
^*Correspondence e-mail: orhanb@omu.edu.tr

(Received 31 July 2009; accepted 15 August 2009; online 22 August 2009)

In the title compound, C₁₄H₁₆BrNO₅, the isoxazolidine ring adopts an envelope conformation, with the N atom at the flap. In the crystal, intermolecular C—H⋯N and C—H⋯O hydrogen bonds generate R₃³(18) ring motifs which are fused into a ribbon-like structure extending along the b axis.

Related literature

For general background, see: Confalone & Huie (1988 ); Torssell (1988 ); Frederickson (1997 ); Gothelf & Jorgensen (1998 ); Chiacchio et al. (2003 ); Padwa et al. (1981 , 1984 ); Ochiai et al. (1967 ); Baldwin & Aube (1987 ); Heaney et al. (2001 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ); Etter (1990 ). For ring conformations, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₄H₁₆BrNO₅
M_r = 358.19
Monoclinic, P 2₁ /c
a = 10.9020 (4) Å
b = 8.1780 (3) Å
c = 17.8127 (8) Å
β = 101.622 (3)°
V = 1555.56 (11) Å³
Z = 4
Mo Kα radiation
μ = 2.67 mm⁻¹
T = 296 K
0.71 × 0.60 × 0.45 mm

Data collection

Stoe IPDS II diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.327, T_max = 0.480
15678 measured reflections
3232 independent reflections
2696 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.101
S = 1.12
3232 reflections
193 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.93 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯N1ⁱ	0.93	2.56	3.492 (4)	179
C12—H12C⋯O1ⁱⁱ	0.96	2.52	3.434 (5)	158
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x, y+1, 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, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809032462/ci2876sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809032462/ci2876Isup2.hkl

checkCIF report

Comment top

The 1,3-dipolar cycloaddition of nitrones and alkenes is a powerful synthetic device that allows up to three new stereogenic centers to be assembled in a stereospecific manner in a single step (Confalone & Huie, 1988; Torssell, 1988; Frederickson, 1997; Gothelf & Jorgensen, 1998). Among these N and O containing five-membered heterocycles, isoxazolidines and isoxazoline derivatives have emerged as important candidates and have been shown to display useful anticancer and antiviral properties (Chiacchio et al., 2003).

The syntheses of isoxazolidine derivatives is an important subject in organic chemistry because they are found in the structure of most natural compounds and drugs. In recent years, isoxazolidine derivatives have been synthesized in high yield via intermolecular cycloaddition of N-methylnitrone with disubstituted olefins and are employed for biological evaluation.

These isoxazolidines are used in the syntheses of β-lactams (Padwa et al., 1981) which are of value in the treatment of bacterial infections (Ochiai et al., 1967), occur as natural products (Baldwin & Aube, 1987), serve as versatile synthetic intermediates (Padwa et al., 1984), and are biologically interesting compounds. In view of the interest shown in these compounds, we report herein the crystal structure of the title compound, (I).

The overall view and atom-labelling of the molecule of (I) are displayed in Fig. 1. The isoxazolidine ring (O1/N1/C7-C9) adopts an envelope conformation, with atom N1 displaced by 0.326 (2) Å from the plane of the other ring atoms (Cremer & Pople, 1975).

The crystal packing is stabilized by intermolecular C—H···N and C—H···O hydrogen bonds (Table 1). As shown in Fig. 2, these hydrogen bonds form R₃³(18) motifs which are fused to form ribbon-like structure extending along the b axis.

Related literature top

For general background, see: Confalone & Huie (1988); Torssell (1988); Frederickson (1997); Gothelf & Jorgensen (1998); Chiacchio et al. (2003); Padwa et al. (1981, 1984); Ochiai et al. (1967); Baldwin & Aube (1987); Heaney et al. (2001). For hydrogen-bond motifs, see: Bernstein et al. (1995); Etter (1990). For ring conformations, see: Cremer & Pople (1975).

Experimental top

N-Methyl-C-(4-bromophenyl)nitrone was prepared from 4-bromo benzaldehyde, N-methyl-hydroxylamine hydrochloride and sodium carbonate in CH₂Cl₂ according to the literature method (Heaney et al., 2001). For the preparation of the title compound, N-methyl-C-(4-bromophenyl) nitrone (453 mg, 3 mmol) and dimethylmaleate (475 mg, 3,3 mmol) were dissolved in benzene (50 ml). The reaction mixture was refluxed for 9 h, and monitored by TLC. After evaporation of the solvent, the reaction mixture was separated by column chromatography, using a mixture of hexane-ethyl acetate (1:2) as the eluent. The trans-isomer was recrystallized from methanol in 3 d (m.p. 354–355 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. A view of (I) with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Part of the crystal structure of (I), showing the formation of hydrogen-bonded R₃³(18) motifs. H atoms not involved in hydrogen bonds have been omitted for clarity. Dashed lines indicate hydrogen bonds. [Symmetry codes: (i) x, 1 + y, z; (ii) 1 - x, 1/2 + y, 1/2 - z; (iii) 1 - x, y - 1/2, 1/2 - z].
	Fig. 3. Preparation of the title compound.

(3R,4S,5R)-Dimethyl trans-3-(4-bromophenyl)-2-methylisoxazolidine-4,5-dicarboxylate top

Crystal data top

C₁₄H₁₆BrNO₅	F(000) = 728
M_r = 358.19	D_x = 1.529 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 15678 reflections
a = 10.9020 (4) Å	θ = 1.9–28.0°
b = 8.1780 (3) Å	µ = 2.67 mm⁻¹
c = 17.8127 (8) Å	T = 296 K
β = 101.622 (3)°	Block, colourless
V = 1555.56 (11) Å³	0.71 × 0.60 × 0.45 mm
Z = 4

Data collection top

Stoe IPDS II diffractometer	3232 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2696 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.043
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.5°, θ_min = 1.9°
ω–scan rotation method	h = −13→13
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −10→10
T_min = 0.327, T_max = 0.480	l = −22→22
15678 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.101	H-atom parameters constrained
S = 1.12	w = 1/[σ²(F_o²) + (0.0399P)² + 1.0321P] where P = (F_o² + 2F_c²)/3
3232 reflections	(Δ/σ)_max = 0.001
193 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.93 e Å⁻³

Crystal data top

C₁₄H₁₆BrNO₅	V = 1555.56 (11) Å³
M_r = 358.19	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.9020 (4) Å	µ = 2.67 mm⁻¹
b = 8.1780 (3) Å	T = 296 K
c = 17.8127 (8) Å	0.71 × 0.60 × 0.45 mm
β = 101.622 (3)°

Data collection top

Stoe IPDS II diffractometer	3232 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	2696 reflections with I > 2σ(I)
T_min = 0.327, T_max = 0.480	R_int = 0.043
15678 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 1.12	Δρ_max = 0.49 e Å⁻³
3232 reflections	Δρ_min = −0.93 e Å⁻³
193 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
C2	0.4201 (3)	0.5503 (4)	0.18030 (16)	0.0460 (7)
H2	0.4149	0.4978	0.2259	0.055*
C8	0.1314 (2)	0.4572 (3)	0.16330 (15)	0.0371 (5)
H8	0.1754	0.5207	0.2072	0.044*
C5	0.4354 (3)	0.7096 (5)	0.04589 (18)	0.0617 (9)
H5	0.4399	0.7642	0.0007	0.074*
C12	0.0010 (4)	0.8290 (4)	0.0637 (3)	0.0793 (12)
H12C	0.0311	0.9380	0.0761	0.095*
H12B	−0.0850	0.8216	0.0685	0.095*
H12A	0.0074	0.8037	0.0120	0.095*
C11	0.0347 (3)	0.5632 (3)	0.11402 (16)	0.0403 (6)
O3	0.0753 (2)	0.7144 (3)	0.11549 (15)	0.0625 (6)
C10	0.3202 (3)	0.1297 (5)	0.1037 (2)	0.0643 (9)
H10C	0.3990	0.1723	0.0965	0.077*
H10B	0.2642	0.1192	0.0549	0.077*
H10A	0.3329	0.0243	0.1278	0.077*
C4	0.5204 (3)	0.7411 (4)	0.11187 (18)	0.0473 (7)
C6	0.3420 (3)	0.5947 (5)	0.04732 (18)	0.0575 (8)
H6	0.2844	0.5715	0.0025	0.069*
N1	0.2659 (2)	0.2410 (3)	0.15238 (14)	0.0448 (5)
O1	0.14367 (19)	0.1690 (2)	0.15537 (13)	0.0506 (5)
O2	−0.0615 (2)	0.5161 (3)	0.07465 (15)	0.0670 (7)
C13	−0.0534 (3)	0.2653 (4)	0.17647 (19)	0.0497 (7)
C14	−0.2378 (3)	0.3749 (6)	0.2055 (3)	0.0783 (12)
H14C	−0.2637	0.4566	0.2378	0.094*
H14B	−0.2667	0.2696	0.2183	0.094*
H14A	−0.2728	0.3994	0.1529	0.094*
O4	−0.1095 (2)	0.1619 (3)	0.1377 (2)	0.0846 (9)
O5	−0.1029 (2)	0.3738 (3)	0.21707 (14)	0.0628 (6)
Br1	0.64870 (3)	0.89981 (5)	0.11195 (2)	0.06568 (15)
C3	0.5147 (3)	0.6630 (4)	0.17970 (17)	0.0462 (7)
H3	0.5732	0.6857	0.2242	0.055*
C7	0.2260 (2)	0.3988 (3)	0.11494 (15)	0.0385 (6)
H7	0.1817	0.3788	0.0622	0.046*
C9	0.0865 (3)	0.2939 (4)	0.19170 (16)	0.0432 (6)
H9	0.1185	0.2863	0.2471	0.052*
C1	0.3332 (2)	0.5142 (4)	0.11427 (15)	0.0400 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C2	0.0426 (14)	0.0554 (18)	0.0379 (14)	−0.0027 (13)	0.0028 (12)	0.0067 (13)
C8	0.0342 (12)	0.0394 (14)	0.0357 (13)	−0.0002 (11)	0.0024 (11)	−0.0037 (11)
C5	0.0592 (19)	0.082 (3)	0.0438 (17)	−0.0175 (18)	0.0108 (15)	0.0108 (17)
C12	0.089 (3)	0.0383 (18)	0.097 (3)	0.0084 (18)	−0.013 (2)	0.005 (2)
C11	0.0381 (13)	0.0392 (15)	0.0430 (14)	0.0014 (11)	0.0070 (12)	−0.0011 (12)
O3	0.0635 (14)	0.0341 (11)	0.0769 (15)	−0.0017 (10)	−0.0164 (12)	−0.0014 (11)
C10	0.060 (2)	0.061 (2)	0.075 (2)	0.0151 (17)	0.0198 (18)	−0.0072 (18)
C4	0.0387 (14)	0.0532 (17)	0.0517 (17)	−0.0047 (13)	0.0135 (13)	−0.0030 (14)
C6	0.0530 (17)	0.081 (2)	0.0361 (15)	−0.0153 (17)	0.0021 (13)	0.0038 (16)
N1	0.0378 (11)	0.0448 (14)	0.0520 (14)	0.0067 (10)	0.0094 (11)	0.0022 (11)
O1	0.0472 (11)	0.0391 (11)	0.0675 (14)	0.0010 (9)	0.0162 (10)	0.0016 (10)
O2	0.0493 (12)	0.0642 (16)	0.0749 (16)	−0.0133 (11)	−0.0174 (12)	0.0165 (13)
C13	0.0463 (16)	0.0454 (17)	0.0604 (18)	0.0012 (14)	0.0176 (15)	0.0068 (15)
C14	0.0518 (19)	0.094 (3)	0.095 (3)	0.012 (2)	0.030 (2)	0.002 (2)
O4	0.0544 (14)	0.0595 (16)	0.142 (3)	−0.0144 (12)	0.0256 (17)	−0.0311 (18)
O5	0.0482 (12)	0.0809 (17)	0.0622 (14)	0.0056 (11)	0.0182 (11)	−0.0075 (12)
Br1	0.0557 (2)	0.0767 (3)	0.0680 (2)	−0.02186 (17)	0.02031 (16)	0.00019 (19)
C3	0.0383 (14)	0.0518 (17)	0.0452 (15)	−0.0021 (12)	0.0007 (12)	−0.0004 (14)
C7	0.0352 (12)	0.0441 (15)	0.0345 (13)	0.0012 (11)	0.0026 (10)	0.0000 (12)
C9	0.0434 (14)	0.0454 (16)	0.0414 (14)	0.0032 (12)	0.0102 (12)	0.0049 (13)
C1	0.0352 (13)	0.0477 (16)	0.0361 (13)	0.0005 (12)	0.0046 (11)	0.0011 (12)

Geometric parameters (Å, º) top

C2—C3	1.385 (4)	C10—H10A	0.96
C2—C1	1.386 (4)	C4—C3	1.379 (4)
C2—H2	0.93	C4—Br1	1.908 (3)
C8—C11	1.503 (4)	C6—C1	1.382 (4)
C8—C9	1.542 (4)	C6—H6	0.93
C8—C7	1.547 (3)	N1—O1	1.468 (3)
C8—H8	0.98	N1—C7	1.478 (4)
C5—C4	1.367 (5)	O1—C9	1.419 (3)
C5—C6	1.390 (5)	C13—O4	1.181 (4)
C5—H5	0.93	C13—O5	1.326 (4)
C12—O3	1.444 (4)	C13—C9	1.512 (4)
C12—H12C	0.96	C14—O5	1.444 (4)
C12—H12B	0.96	C14—H14C	0.96
C12—H12A	0.96	C14—H14B	0.96
C11—O2	1.202 (4)	C14—H14A	0.96
C11—O3	1.312 (4)	C3—H3	0.93
C10—N1	1.462 (4)	C7—C1	1.505 (4)
C10—H10C	0.96	C7—H7	0.98
C10—H10B	0.96	C9—H9	0.98

C3—C2—C1	121.2 (3)	C5—C6—H6	119.5
C3—C2—H2	119.4	C10—N1—O1	104.5 (2)
C1—C2—H2	119.4	C10—N1—C7	113.2 (2)
C11—C8—C9	117.3 (2)	O1—N1—C7	100.31 (19)
C11—C8—C7	108.7 (2)	C9—O1—N1	102.4 (2)
C9—C8—C7	101.9 (2)	O4—C13—O5	125.3 (3)
C11—C8—H8	109.5	O4—C13—C9	126.9 (3)
C9—C8—H8	109.5	O5—C13—C9	107.7 (3)
C7—C8—H8	109.5	O5—C14—H14C	109.5
C4—C5—C6	119.0 (3)	O5—C14—H14B	109.5
C4—C5—H5	120.5	H14C—C14—H14B	109.5
C6—C5—H5	120.5	O5—C14—H14A	109.5
O3—C12—H12C	109.5	H14C—C14—H14A	109.5
O3—C12—H12B	109.5	H14B—C14—H14A	109.5
H12C—C12—H12B	109.5	C13—O5—C14	116.2 (3)
O3—C12—H12A	109.5	C4—C3—C2	118.7 (3)
H12C—C12—H12A	109.5	C4—C3—H3	120.6
H12B—C12—H12A	109.5	C2—C3—H3	120.6
O2—C11—O3	124.4 (3)	N1—C7—C1	113.1 (2)
O2—C11—C8	125.7 (3)	N1—C7—C8	100.8 (2)
O3—C11—C8	109.8 (2)	C1—C7—C8	114.6 (2)
C11—O3—C12	117.1 (3)	N1—C7—H7	109.3
N1—C10—H10C	109.5	C1—C7—H7	109.3
N1—C10—H10B	109.5	C8—C7—H7	109.3
H10C—C10—H10B	109.5	O1—C9—C13	109.1 (2)
N1—C10—H10A	109.5	O1—C9—C8	106.0 (2)
H10C—C10—H10A	109.5	C13—C9—C8	116.8 (2)
H10B—C10—H10A	109.5	O1—C9—H9	108.2
C5—C4—C3	121.5 (3)	C13—C9—H9	108.2
C5—C4—Br1	120.0 (2)	C8—C9—H9	108.2
C3—C4—Br1	118.5 (2)	C6—C1—C2	118.5 (3)
C1—C6—C5	121.1 (3)	C6—C1—C7	119.6 (3)
C1—C6—H6	119.5	C2—C1—C7	121.8 (2)

C9—C8—C11—O2	−25.5 (4)	C9—C8—C7—N1	−26.7 (2)
C7—C8—C11—O2	89.3 (3)	C11—C8—C7—C1	87.0 (3)
C9—C8—C11—O3	159.4 (2)	C9—C8—C7—C1	−148.5 (2)
C7—C8—C11—O3	−85.8 (3)	N1—O1—C9—C13	161.6 (2)
O2—C11—O3—C12	−2.7 (5)	N1—O1—C9—C8	35.1 (3)
C8—C11—O3—C12	172.4 (3)	O4—C13—C9—O1	−3.5 (5)
C6—C5—C4—C3	−0.8 (5)	O5—C13—C9—O1	174.0 (2)
C6—C5—C4—Br1	−179.4 (3)	O4—C13—C9—C8	116.5 (4)
C4—C5—C6—C1	0.8 (6)	O5—C13—C9—C8	−65.9 (3)
C10—N1—O1—C9	−170.5 (2)	C11—C8—C9—O1	113.7 (3)
C7—N1—O1—C9	−53.0 (2)	C7—C8—C9—O1	−4.9 (3)
O4—C13—O5—C14	−7.2 (5)	C11—C8—C9—C13	−8.0 (4)
C9—C13—O5—C14	175.2 (3)	C7—C8—C9—C13	−126.6 (3)
C5—C4—C3—C2	0.0 (5)	C5—C6—C1—C2	−0.2 (5)
Br1—C4—C3—C2	178.6 (2)	C5—C6—C1—C7	176.0 (3)
C1—C2—C3—C4	0.7 (5)	C3—C2—C1—C6	−0.6 (5)
C10—N1—C7—C1	−77.9 (3)	C3—C2—C1—C7	−176.7 (3)
O1—N1—C7—C1	171.2 (2)	N1—C7—C1—C6	133.1 (3)
C10—N1—C7—C8	159.2 (2)	C8—C7—C1—C6	−112.1 (3)
O1—N1—C7—C8	48.3 (2)	N1—C7—C1—C2	−50.9 (4)
C11—C8—C7—N1	−151.2 (2)	C8—C7—C1—C2	63.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N1ⁱ	0.93	2.56	3.492 (4)	179
C12—H12C···O1ⁱⁱ	0.96	2.52	3.434 (5)	158

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₆BrNO₅
M_r	358.19
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	10.9020 (4), 8.1780 (3), 17.8127 (8)
β (°)	101.622 (3)
V (Å³)	1555.56 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.67
Crystal size (mm)	0.71 × 0.60 × 0.45

Data collection
Diffractometer	Stoe IPDS II diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.327, 0.480
No. of measured, independent and observed [I > 2σ(I)] reflections	15678, 3232, 2696
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.101, 1.12
No. of reflections	3232
No. of parameters	193
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.93

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
C3—H3···N1ⁱ	0.93	2.56	3.492 (4)	179
C12—H12C···O1ⁱⁱ	0.96	2.52	3.434 (5)	158

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

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 F.279 of the University Research Fund).

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