Dimethyl 4-eth­oxy-1-(4-methyl-2-pyri­dyl)-5-oxo-2,5-dihydro-1H-pyrrole-2,3-dicarboxyl­ate

Anary-Abbasinejad, M.; Mirhosseini, M.; Tabatabaee, M.

doi:10.1107/S1600536810012882

organic compounds

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ISSN: 2056-9890

Volume 66| Part 5| May 2010| Page o1101

https://doi.org/10.1107/S1600536810012882

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Dimethyl 4-ethoxy-1-(4-methyl-2-pyridyl)-5-oxo-2,5-dihydro-1H-pyrrole-2,3-dicarboxylate

Mohammad Anary-Abbasinejad,^a Marziyeh Mirhosseini ^a and Masoumeh Tabatabaee ^a ^*

^aDepartment of Chemistry, Islamic Azad University Yazd Branch, Yazd, Iran
^*Correspondence e-mail: tabatabaee45m@yahoo.com

(Received 3 April 2010; accepted 7 April 2010; online 17 April 2010)

In the title compound, C₁₆H₁₈N₂O₆, the dihedral angle between the aromatic ring planes is 8.11 (6)°. One of the O atoms is disordered over two sites of equal occupancy. In the crystal structure, aromatic π–π stacking [centroid-to-centroid separation = 3.5503 (8) Å] helps to consolidate the packing.

Related literature

For background on 3-pyrrolines as synthetic intermediates, see: Tarnchompoo et al. (1987 ); Bienz et al. (1989 ). For further synthetic details, see: Anary-Abbasinejad et al. (2010 ).

Experimental

Crystal data

C₁₆H₁₈N₂O₆
M_r = 334.32
Triclinic, $[P \overline 1]$
a = 9.2674 (6) Å
b = 9.4219 (6) Å
c = 10.7650 (7) Å
α = 87.692 (2)°
β = 72.037 (1)°
γ = 61.797 (1)°
V = 781.73 (9) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 120 K
0.22 × 0.19 × 0.15 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.976, T_max = 0.984
14075 measured reflections
4340 independent reflections
3811 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.119
S = 1.00
4340 reflections
231 parameters
8 restraints
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810012882/hb5395sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810012882/hb5395Isup2.hkl

checkCIF report

Comment top

(N-Substituted 3-pyrrolines serve as useful synthetic intermediates (Tarnchompoo et al., 1987; Bienz et al., 1989). Recently we reported a one-pot procedure for the synthesis of some dialkyl N-(3-methyl-2-pyridyl)-4-ethoxy-5-oxo-2,5-dihydro-1H- pyrole-2,3-dicarboxylate derivatives (Anary-Abbasinejad et al., 2010).

Here we report the synthesis and crystal structure of the title compound, (I). It is rational to assume that compound 1 (Fig. 1) is produced from the initial production of ylide intermediate produced from three-component reaction of DMAD, 4-methyl-2-aminopyridine and triphenylphosphine, which then reacted with ethyl chlorooxoacetate to produce an oxamate derivative that underwent intramolecular Wittig reaction to give the products. Crystal packing of I is shown in Fig. 2. A considerable feature of the compound (I) is the presence of π–π stacking interactions between six and five membered rings (Fig. 3) with distance 3.5503 (8) Å for Cg2···Cg3 (Cg2 = N1/C10–C17 and Cg3 = N2/C9–C12).

Related literature top

For background on 3-pyrrolines as synthetic intermediates, see: Tarnchompoo et al. (1987); Bienz et al. (1989). For further synthetic details, see: Anary-Abbasinejad et al. (2010).

Experimental top

To a magnetically stirred solution of PPh₃ (0.26 g, 1 mmol) and 4-methyl-2-aminopyridine (0.9 g, 1 mmol) in CH₂Cl₂(10 ml) was added drop-wise a mixture of dimethyl acetylenedicarboxylate DMAD (0.14 g, 1 mmol) in CH₂Cl₂ (3 ml) at room temperature over 2 min. The reaction mixture was then stirred for one more minute, then triethylamine (1 mmol) and ethyl chlorooxoacetate (1 mmol) was added and the reaction mixture was stirred for more 24 h. Solvent was evaporated and the residue was purified by column chromatography on SiO₂ using EtOAC–hexane (1:4) mixture as eluent. The solid formed was filtrated, recrystallised from dichloromethane/ethanol (2:1) to yield colourless prisms of (I).

Structure description top

For background on 3-pyrrolines as synthetic intermediates, see: Tarnchompoo et al. (1987); Bienz et al. (1989). For further synthetic details, see: Anary-Abbasinejad et al. (2010).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I). Atoms are represented by 50% displacement ellipsoids. The occupancies of positions of disordered O6 atom are equal (0.5).
	Fig. 2. The overview of I crystal packing. Atoms are represented by spheres.
	Fig. 3. Representation of π–π stacking in I.

Dimethyl 4-ethoxy-1-(4-methyl-2-pyridyl)-5-oxo-2,5-dihydro- 1H-pyrrole-2,3-dicarboxylate top

Crystal data top

C₁₆H₁₈N₂O₆	Z = 2
M_r = 334.32	F(000) = 352
Triclinic, P1	D_x = 1.420 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2674 (6) Å	Cell parameters from 259 reflections
b = 9.4219 (6) Å	θ = 3–29°
c = 10.7650 (7) Å	µ = 0.11 mm⁻¹
α = 87.692 (2)°	T = 120 K
β = 72.037 (1)°	Prism, colourless
γ = 61.797 (1)°	0.22 × 0.19 × 0.15 mm
V = 781.73 (9) Å³

Data collection top

Bruker SMART 1000 CCD diffractometer	4340 independent reflections
Radiation source: fine-focus sealed tube	3811 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ω scans	θ_max = 29.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −12→12
T_min = 0.976, T_max = 0.984	k = −13→13
14075 measured reflections	l = −14→14

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0685P)² + 0.3063P] where P = (F_o² + 2F_c²)/3
4340 reflections	(Δ/σ)_max = 0.001
231 parameters	Δρ_max = 0.37 e Å⁻³
8 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₆H₁₈N₂O₆	γ = 61.797 (1)°
M_r = 334.32	V = 781.73 (9) Å³
Triclinic, P1	Z = 2
a = 9.2674 (6) Å	Mo Kα radiation
b = 9.4219 (6) Å	µ = 0.11 mm⁻¹
c = 10.7650 (7) Å	T = 120 K
α = 87.692 (2)°	0.22 × 0.19 × 0.15 mm
β = 72.037 (1)°

Data collection top

Bruker SMART 1000 CCD diffractometer	4340 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	3811 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.984	R_int = 0.020
14075 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	8 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.00	Δρ_max = 0.37 e Å⁻³
4340 reflections	Δρ_min = −0.29 e Å⁻³
231 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 > 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	Occ. (<1)
O1	0.17590 (10)	0.52219 (10)	0.39546 (8)	0.02303 (17)
O2	0.40451 (10)	0.95161 (9)	0.14840 (8)	0.02268 (17)
O3	0.51098 (11)	0.79492 (10)	0.29618 (8)	0.02475 (18)
N1	0.71510 (11)	0.58162 (11)	−0.02268 (9)	0.01973 (18)
O4	−0.06090 (10)	0.84294 (10)	0.37603 (9)	0.02895 (19)
O5	0.54578 (10)	0.30748 (9)	0.25074 (8)	0.02478 (18)
N2	0.52930 (11)	0.53670 (10)	0.15196 (8)	0.01807 (17)
C8	0.44689 (12)	0.82101 (12)	0.21038 (10)	0.01806 (19)
C9	0.39637 (12)	0.70530 (12)	0.16169 (10)	0.01788 (19)
H9A	0.3761	0.7310	0.0756	0.021*
C10	0.69758 (12)	0.47752 (12)	0.06007 (9)	0.01754 (19)
C11	1.01376 (13)	0.37860 (13)	−0.12410 (10)	0.0217 (2)
H11A	1.1218	0.3474	−0.1911	0.026*
C12	0.46748 (13)	0.45026 (12)	0.23786 (10)	0.01882 (19)
C13	0.23818 (13)	0.71222 (12)	0.26432 (10)	0.01865 (19)
C14	0.83205 (13)	0.32265 (12)	0.05951 (10)	0.0201 (2)
H14A	0.8133	0.2538	0.1220	0.024*
C15	0.28055 (13)	0.56764 (12)	0.30958 (10)	0.0190 (2)
C16	0.99386 (13)	0.27226 (13)	−0.03493 (10)	0.0209 (2)
C17	0.87312 (13)	0.53027 (13)	−0.11305 (10)	0.0216 (2)
H17A	0.8889	0.6027	−0.1729	0.026*
C18	0.07123 (14)	0.86461 (13)	0.30661 (11)	0.0230 (2)
C20	0.23239 (15)	0.44492 (14)	0.50530 (11)	0.0242 (2)
H20A	0.3508	0.3514	0.4706	0.029*
H20B	0.1538	0.4040	0.5559	0.029*
C21	1.14368 (15)	0.10896 (14)	−0.03822 (13)	0.0295 (2)
H21A	1.2431	0.1216	−0.0393	0.044*
H21B	1.1749	0.0388	−0.1175	0.044*
H21C	1.1108	0.0598	0.0400	0.044*
C22	0.40700 (15)	1.08725 (13)	0.20518 (12)	0.0263 (2)
H22A	0.4173	1.1584	0.1380	0.039*
H22B	0.5061	1.0464	0.2372	0.039*
H22C	0.2993	1.1485	0.2787	0.039*
C23	−0.22672 (15)	0.98915 (16)	0.42475 (13)	0.0347 (3)
H23A	−0.3177	0.9600	0.4659	0.052*
H23B	−0.2518	1.0504	0.3514	0.052*
H23C	−0.2230	1.0560	0.4899	0.052*
C24	0.23145 (19)	0.56449 (17)	0.59437 (13)	0.0351 (3)
H24A	0.2595	0.5142	0.6712	0.053*
H24B	0.1163	0.6606	0.6235	0.053*
H24C	0.3179	0.5966	0.5465	0.053*
O6'	0.0517 (16)	0.9913 (13)	0.2663 (9)	0.0417 (17)	0.50
O6	0.0634 (17)	0.9971 (12)	0.2975 (10)	0.0393 (15)	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0207 (4)	0.0295 (4)	0.0238 (4)	−0.0162 (3)	−0.0077 (3)	0.0093 (3)
O2	0.0264 (4)	0.0174 (3)	0.0276 (4)	−0.0124 (3)	−0.0107 (3)	0.0065 (3)
O3	0.0280 (4)	0.0229 (4)	0.0262 (4)	−0.0124 (3)	−0.0126 (3)	0.0039 (3)
N1	0.0194 (4)	0.0210 (4)	0.0196 (4)	−0.0107 (3)	−0.0058 (3)	0.0030 (3)
O4	0.0168 (4)	0.0254 (4)	0.0354 (4)	−0.0078 (3)	−0.0006 (3)	0.0022 (3)
O5	0.0237 (4)	0.0182 (4)	0.0318 (4)	−0.0108 (3)	−0.0076 (3)	0.0060 (3)
N2	0.0161 (4)	0.0154 (4)	0.0202 (4)	−0.0072 (3)	−0.0033 (3)	0.0018 (3)
C8	0.0155 (4)	0.0157 (4)	0.0198 (4)	−0.0070 (3)	−0.0028 (3)	0.0017 (3)
C9	0.0168 (4)	0.0166 (4)	0.0192 (4)	−0.0078 (4)	−0.0049 (3)	0.0024 (3)
C10	0.0175 (4)	0.0184 (4)	0.0175 (4)	−0.0097 (4)	−0.0048 (3)	0.0001 (3)
C11	0.0188 (4)	0.0264 (5)	0.0197 (4)	−0.0118 (4)	−0.0044 (3)	0.0003 (4)
C12	0.0195 (4)	0.0188 (4)	0.0204 (4)	−0.0111 (4)	−0.0063 (3)	0.0024 (3)
C13	0.0168 (4)	0.0204 (5)	0.0190 (4)	−0.0096 (4)	−0.0051 (3)	0.0017 (3)
C14	0.0192 (4)	0.0181 (4)	0.0217 (5)	−0.0086 (4)	−0.0059 (4)	0.0015 (3)
C15	0.0181 (4)	0.0213 (5)	0.0202 (4)	−0.0118 (4)	−0.0059 (3)	0.0030 (3)
C16	0.0183 (4)	0.0208 (5)	0.0223 (5)	−0.0082 (4)	−0.0065 (4)	−0.0008 (4)
C17	0.0215 (5)	0.0250 (5)	0.0196 (4)	−0.0128 (4)	−0.0061 (4)	0.0037 (4)
C18	0.0197 (5)	0.0227 (5)	0.0223 (5)	−0.0085 (4)	−0.0044 (4)	0.0024 (4)
C20	0.0246 (5)	0.0249 (5)	0.0242 (5)	−0.0133 (4)	−0.0081 (4)	0.0090 (4)
C21	0.0199 (5)	0.0238 (5)	0.0350 (6)	−0.0051 (4)	−0.0052 (4)	0.0027 (4)
C22	0.0280 (5)	0.0168 (5)	0.0329 (6)	−0.0120 (4)	−0.0065 (4)	0.0016 (4)
C23	0.0176 (5)	0.0322 (6)	0.0358 (6)	−0.0034 (5)	0.0009 (4)	0.0014 (5)
C24	0.0472 (7)	0.0378 (7)	0.0276 (6)	−0.0245 (6)	−0.0155 (5)	0.0082 (5)
O6'	0.026 (2)	0.026 (2)	0.051 (4)	−0.0063 (13)	0.004 (2)	0.014 (2)
O6	0.0263 (16)	0.0202 (13)	0.058 (4)	−0.0087 (11)	−0.002 (3)	0.004 (2)

Geometric parameters (Å, º) top

O1—C15	1.3364 (12)	C13—C18	1.4769 (14)
O1—C20	1.4679 (13)	C14—C16	1.3904 (14)
O2—C8	1.3238 (12)	C14—H14A	0.9500
O2—C22	1.4515 (13)	C16—C21	1.5004 (15)
O3—C8	1.2035 (13)	C17—H17A	0.9500
N1—C10	1.3315 (13)	C18—O6'	1.204 (10)
N1—C17	1.3471 (13)	C18—O6	1.218 (10)
O4—C18	1.3263 (13)	C20—C24	1.5037 (17)
O4—C23	1.4472 (14)	C20—H20A	0.9900
O5—C12	1.2165 (13)	C20—H20B	0.9900
N2—C12	1.3785 (12)	C21—H21A	0.9800
N2—C10	1.4115 (12)	C21—H21B	0.9800
N2—C9	1.4615 (12)	C21—H21C	0.9800
C8—C9	1.5369 (14)	C22—H22A	0.9800
C9—C13	1.5134 (13)	C22—H22B	0.9800
C9—H9A	1.0000	C22—H22C	0.9800
C10—C14	1.3999 (14)	C23—H23A	0.9800
C11—C17	1.3830 (15)	C23—H23B	0.9800
C11—C16	1.3954 (15)	C23—H23C	0.9800
C11—H11A	0.9500	C24—H24A	0.9800
C12—C15	1.5011 (14)	C24—H24B	0.9800
C13—C15	1.3440 (14)	C24—H24C	0.9800

C15—O1—C20	116.43 (8)	N1—C17—H17A	118.0
C8—O2—C22	116.22 (9)	C11—C17—H17A	118.0
C10—N1—C17	116.47 (9)	O6'—C18—O4	122.5 (6)
C18—O4—C23	115.57 (9)	O6—C18—O4	123.7 (6)
C12—N2—C10	127.04 (9)	O6'—C18—C13	123.4 (6)
C12—N2—C9	112.20 (8)	O6—C18—C13	121.9 (6)
C10—N2—C9	120.74 (8)	O4—C18—C13	113.18 (9)
O3—C8—O2	126.28 (10)	O1—C20—C24	110.36 (9)
O3—C8—C9	123.12 (9)	O1—C20—H20A	109.6
O2—C8—C9	110.56 (8)	C24—C20—H20A	109.6
N2—C9—C13	102.82 (8)	O1—C20—H20B	109.6
N2—C9—C8	110.34 (8)	C24—C20—H20B	109.6
C13—C9—C8	110.24 (8)	H20A—C20—H20B	108.1
N2—C9—H9A	111.1	C16—C21—H21A	109.5
C13—C9—H9A	111.1	C16—C21—H21B	109.5
C8—C9—H9A	111.1	H21A—C21—H21B	109.5
N1—C10—C14	124.23 (9)	C16—C21—H21C	109.5
N1—C10—N2	114.20 (9)	H21A—C21—H21C	109.5
C14—C10—N2	121.57 (9)	H21B—C21—H21C	109.5
C17—C11—C16	118.70 (9)	O2—C22—H22A	109.5
C17—C11—H11A	120.7	O2—C22—H22B	109.5
C16—C11—H11A	120.7	H22A—C22—H22B	109.5
O5—C12—N2	127.50 (10)	O2—C22—H22C	109.5
O5—C12—C15	126.81 (9)	H22A—C22—H22C	109.5
N2—C12—C15	105.66 (8)	H22B—C22—H22C	109.5
C15—C13—C18	129.15 (9)	O4—C23—H23A	109.5
C15—C13—C9	109.65 (9)	O4—C23—H23B	109.5
C18—C13—C9	121.10 (9)	H23A—C23—H23B	109.5
C16—C14—C10	118.22 (10)	O4—C23—H23C	109.5
C16—C14—H14A	120.9	H23A—C23—H23C	109.5
C10—C14—H14A	120.9	H23B—C23—H23C	109.5
O1—C15—C13	127.97 (9)	C20—C24—H24A	109.5
O1—C15—C12	122.13 (9)	C20—C24—H24B	109.5
C13—C15—C12	109.62 (9)	H24A—C24—H24B	109.5
C14—C16—C11	118.34 (10)	C20—C24—H24C	109.5
C14—C16—C21	120.49 (10)	H24A—C24—H24C	109.5
C11—C16—C21	121.16 (10)	H24B—C24—H24C	109.5
N1—C17—C11	124.02 (10)

C22—O2—C8—O3	−11.71 (15)	C20—O1—C15—C13	−130.46 (11)
C22—O2—C8—C9	166.06 (8)	C20—O1—C15—C12	56.26 (13)
C12—N2—C9—C13	−1.63 (11)	C18—C13—C15—O1	7.41 (18)
C10—N2—C9—C13	176.88 (8)	C9—C13—C15—O1	−176.23 (10)
C12—N2—C9—C8	115.93 (9)	C18—C13—C15—C12	−178.63 (10)
C10—N2—C9—C8	−65.56 (11)	C9—C13—C15—C12	−2.27 (11)
O3—C8—C9—N2	−40.90 (13)	O5—C12—C15—O1	−2.48 (16)
O2—C8—C9—N2	141.24 (8)	N2—C12—C15—O1	175.60 (9)
O3—C8—C9—C13	71.98 (12)	O5—C12—C15—C13	−176.85 (10)
O2—C8—C9—C13	−105.87 (9)	N2—C12—C15—C13	1.22 (11)
C17—N1—C10—C14	1.13 (15)	C10—C14—C16—C11	0.02 (15)
C17—N1—C10—N2	−179.48 (8)	C10—C14—C16—C21	178.63 (9)
C12—N2—C10—N1	171.31 (9)	C17—C11—C16—C14	1.30 (15)
C9—N2—C10—N1	−6.97 (13)	C17—C11—C16—C21	−177.30 (10)
C12—N2—C10—C14	−9.29 (16)	C10—N1—C17—C11	0.34 (15)
C9—N2—C10—C14	172.43 (9)	C16—C11—C17—N1	−1.56 (16)
C10—N2—C12—O5	0.04 (17)	C23—O4—C18—O6'	−12.9 (5)
C9—N2—C12—O5	178.45 (10)	C23—O4—C18—O6	9.6 (5)
C10—N2—C12—C15	−178.01 (9)	C23—O4—C18—C13	177.55 (10)
C9—N2—C12—C15	0.39 (11)	C15—C13—C18—O6'	173.7 (5)
N2—C9—C13—C15	2.39 (11)	C9—C13—C18—O6'	−2.3 (5)
C8—C9—C13—C15	−115.24 (9)	C15—C13—C18—O6	151.4 (5)
N2—C9—C13—C18	179.09 (9)	C9—C13—C18—O6	−24.6 (5)
C8—C9—C13—C18	61.45 (12)	C15—C13—C18—O4	−16.81 (16)
N1—C10—C14—C16	−1.31 (16)	C9—C13—C18—O4	167.21 (9)
N2—C10—C14—C16	179.34 (9)	C15—O1—C20—C24	66.34 (12)

Experimental details

Crystal data
Chemical formula	C₁₆H₁₈N₂O₆
M_r	334.32
Crystal system, space group	Triclinic, P1
Temperature (K)	120
a, b, c (Å)	9.2674 (6), 9.4219 (6), 10.7650 (7)
α, β, γ (°)	87.692 (2), 72.037 (1), 61.797 (1)
V (Å³)	781.73 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.22 × 0.19 × 0.15

Data collection
Diffractometer	Bruker SMART 1000 CCD
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.976, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	14075, 4340, 3811
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.693

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.119, 1.00
No. of reflections	4340
No. of parameters	231
No. of restraints	8
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.29

Computer programs: SMART (Bruker, 1998), SAINT-Plus (Bruker, 1998), SHELXTL (Sheldrick, 2008).

Acknowledgements

The authors are grateful to Islamic Azad University, Yazd Branch, for supporting this work.

References

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