Dimethyl 6-acetyl-2-methyl-1,2-dihydroquinoline-2,4-dicarboxyl­ate

Gültekin, Z.; Bolte, M.; Hökelek, T.

doi:10.1107/S1600536812003650

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o606

doi:10.1107/S1600536812003650

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Dimethyl 6-acetyl-2-methyl-1,2-dihydroquinoline-2,4-dicarboxylate

Zeynep Gültekin,^a Michael Bolte ^b and Tuncer Hökelek ^c ^*

^aDepartment of Chemistry, Çankırı Karatekin University, TR-18100 Çankırı, Turkey, ^bInstitut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, D-60438 Frankfurt/Main, Germany, and ^cDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey
^*Correspondence e-mail: merzifon@hacettepe.edu.tr

(Received 24 January 2012; accepted 27 January 2012; online 4 February 2012)

In the title compound, C₁₆H₁₇NO₅, the dihydropyridine ring adopts a sofa conformation. In the crystal, intermolecular N—H⋯O hydrogen bonds link the molecules into chains running along the b axis.

Related literature

For the methods reported in the literature for the preparation of 1,2-dihydroquinolines, see: Hu et al. (2011 ); Yadav et al. (2007 , 2008 ); Waldmann et al. (2008 ). For the biological activity of dihydroquinolines, see: Craig & Pearson (1971 ); Muren & Weissman (1971 ); Hamann et al. (1998 ); He et al. (2003 ); LaMontagne et al. (1989 ). For related structures, see: Gültekin et al. (2010 ); Gültekin et al. (2011a ,b ). For ring-puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₆H₁₇NO₅
M_r = 303.31
Triclinic, $[P \overline 1]$
a = 7.9853 (7) Å
b = 8.3950 (7) Å
c = 12.4416 (11) Å
α = 89.308 (7)°
β = 74.436 (7)°
γ = 71.568 (7)°
V = 759.82 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 173 K
0.36 × 0.34 × 0.31 mm

Data collection

Stoe IPDS II two-circle diffractometer
12439 measured reflections
2833 independent reflections
2507 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.121
S = 1.05
2833 reflections
207 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O5ⁱ	0.85 (2)	2.10 (2)	2.9223 (19)	166 (2)
Symmetry code: (i) x, y-1, z.

Data collection: X-AREA (Stoe & Cie, 2001 ); cell refinement: X-AREA; data reduction: X-AREA; 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 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812003650/xu5460sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812003650/xu5460Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812003650/xu5460Isup3.cml

checkCIF report

Comment top

1,2-Dihydroquinoline derivatives have been considerably important for the preparation of biologically important compounds (Craig & Pearson, 1971; Muren & Weissman, 1971). Many methods have been reported in the literature for the preparation of 1,2-dihydroquinolines (Yadav et al., 2007, 2008). The most convenient method is the condensation of aromatic amines with ketones using a catalytic amount of a Lewis acid or Brønsted acid (Hu et al., 2011; Waldmann et al., 2008). Dihydroquinolines are also powerful intermediates for the preparation of quinolines and many quinolines display biological effects (Hamann et al., 1998; LaMontagne et al., 1989; He et al., 2003).

The structures of some 1,2-dihydroquinoline derivatives, C₁₆H₁₉NO₄ (Gültekin et al., 2010), C₁₄H₁₅NO₄ (Gültekin et al., 2011a) and C₁₇H₂₁NO₇ (Gültekin et al., 2011b) have also been determined.

In the title compound, (I), (Fig. 1), the ring A (C2–C4/C9/C10/N1) is not planar, but adopting a sofa conformation with puckering parameters (Cremer & Pople, 1975) Q_T = 0.348 (2)Å, ϕ = -45.4 (4)° and θ = 49.3 (3)°.

In the crystal structure, intermolecular N—H···O hydrogen bonds (Table 1) link the molecules to form infinite chains along the b-axis (Fig. 2).

Related literature top

For the methods reported in the literature for the preparation of 1,2-dihydroquinolines, see: Hu et al. (2011); Yadav et al. (2007, 2008); Waldmann et al. (2008). For the biological activity of dihydroquinolines, see: Craig & Pearson (1971); Muren & Weissman (1971); Hamann et al. (1998); He et al. (2003); LaMontagne et al. (1989). For related structures, see: Gültekin et al. (2010); Gültekin et al. (2011a,b). For ring-puckering parameters, see: Cremer & Pople (1975).

Experimental top

The title compound was synthesized by the literature method (Waldmann et al., 2008). p-acetyl aniline (100 mg, 1 eq) was dissolved in acetonitrile (1.5 ml), and then Bi(OTf)₃ (5 mol%, 0.05 eq) and methyl pyruvate (2.2 eq) were added to the mixture. The mixture was heated by microwave irradiation for 3 h until the starting material was completely consumed as monitored by TLC. The resultant residue was directly purified by flash chromatography on silica (EtOAc:Cylohexane 1:2). Recrystallization over pentane and ethyl acetate (70:30) gave a yellow crystalline solid (yield: 91%), R_f 0.31 (2:1 Cyclohexane/EtOAc) m.p.: 425–426 K.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); 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) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A partial packing diagram. Hydrogen bonds are shown as dashed lines.

Dimethyl 6-acetyl-2-methyl-1,2-dihydroquinoline-2,4-dicarboxylate top

Crystal data top

C₁₆H₁₇NO₅	Z = 2
M_r = 303.31	F(000) = 320
Triclinic, P1	D_x = 1.326 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9853 (7) Å	Cell parameters from 11792 reflections
b = 8.3950 (7) Å	θ = 3.5–25.9°
c = 12.4416 (11) Å	µ = 0.10 mm⁻¹
α = 89.308 (7)°	T = 173 K
β = 74.436 (7)°	Block, light brown
γ = 71.568 (7)°	0.36 × 0.34 × 0.31 mm
V = 759.82 (12) Å³

Data collection top

Stoe IPDS II two-circle diffractometer	2507 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.044
Graphite monochromator	θ_max = 25.6°, θ_min = 3.4°
ω scans	h = −9→9
12439 measured reflections	k = −10→10
2833 independent reflections	l = −15→15

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0649P)² + 0.2357P] where P = (F_o² + 2F_c²)/3
2833 reflections	(Δ/σ)_max < 0.001
207 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₆H₁₇NO₅	γ = 71.568 (7)°
M_r = 303.31	V = 759.82 (12) Å³
Triclinic, P1	Z = 2
a = 7.9853 (7) Å	Mo Kα radiation
b = 8.3950 (7) Å	µ = 0.10 mm⁻¹
c = 12.4416 (11) Å	T = 173 K
α = 89.308 (7)°	0.36 × 0.34 × 0.31 mm
β = 74.436 (7)°

Data collection top

Stoe IPDS II two-circle diffractometer	2507 reflections with I > 2σ(I)
12439 measured reflections	R_int = 0.044
2833 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.26 e Å⁻³
2833 reflections	Δρ_min = −0.22 e Å⁻³
207 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
O1	0.6972 (2)	−0.1203 (2)	0.18082 (12)	0.0633 (4)
O2	0.69874 (15)	−0.00298 (16)	0.34026 (9)	0.0414 (3)
O3	0.12719 (16)	0.61353 (14)	0.44347 (9)	0.0371 (3)
O4	0.29430 (17)	0.43432 (16)	0.53946 (10)	0.0443 (3)
O5	0.26090 (17)	0.80610 (14)	0.09807 (10)	0.0407 (3)
N1	0.31769 (19)	0.06145 (17)	0.22877 (11)	0.0332 (3)
H1	0.322 (3)	−0.019 (3)	0.1868 (16)	0.037 (5)*
C2	0.4058 (2)	0.01893 (18)	0.31827 (12)	0.0297 (3)
C3	0.34378 (19)	0.17245 (19)	0.39857 (12)	0.0286 (3)
H3	0.3402	0.1582	0.4733	0.034*
C4	0.29367 (18)	0.32849 (18)	0.36578 (12)	0.0271 (3)
C5	0.27307 (19)	0.50723 (18)	0.20096 (12)	0.0278 (3)
H5	0.2688	0.5999	0.2431	0.033*
C6	0.26233 (19)	0.52543 (19)	0.09059 (12)	0.0285 (3)
C7	0.2661 (2)	0.38508 (19)	0.02853 (12)	0.0312 (3)
H7	0.2549	0.3960	−0.0439	0.037*
C8	0.2861 (2)	0.23170 (19)	0.07329 (13)	0.0317 (3)
H8	0.2896	0.1398	0.0307	0.038*
C9	0.30114 (19)	0.21314 (18)	0.18284 (12)	0.0278 (3)
C10	0.28990 (18)	0.35501 (18)	0.24904 (12)	0.0266 (3)
C11	0.3554 (3)	−0.1283 (2)	0.37615 (15)	0.0416 (4)
H11A	0.3912	−0.2219	0.3219	0.062*
H11B	0.2252	−0.0943	0.4101	0.062*
H11C	0.4185	−0.1609	0.4327	0.062*
C12	0.6168 (2)	−0.04291 (18)	0.26972 (12)	0.0317 (3)
C13	0.8977 (2)	−0.0641 (3)	0.30643 (17)	0.0581 (6)
H13A	0.9424	−0.0192	0.3594	0.087*
H13B	0.9422	−0.0287	0.2337	0.087*
H13C	0.9403	−0.1849	0.3038	0.087*
C14	0.2280 (2)	0.47500 (19)	0.45107 (12)	0.0291 (3)
C15	0.2295 (3)	0.5639 (3)	0.63061 (15)	0.0539 (5)
H15A	0.2683	0.5165	0.6940	0.081*
H15B	0.0977	0.6081	0.6507	0.081*
H15C	0.2795	0.6528	0.6075	0.081*
C16	0.2474 (2)	0.69166 (19)	0.04489 (12)	0.0307 (3)
C17	0.2142 (3)	0.7197 (2)	−0.06869 (14)	0.0419 (4)
H17A	0.1961	0.8356	−0.0833	0.063*
H17B	0.1068	0.6923	−0.0700	0.063*
H17C	0.3186	0.6491	−0.1250	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0535 (8)	0.0781 (10)	0.0459 (8)	−0.0062 (7)	−0.0104 (6)	−0.0292 (7)
O2	0.0269 (6)	0.0580 (8)	0.0346 (6)	−0.0048 (5)	−0.0112 (5)	−0.0073 (5)
O3	0.0436 (6)	0.0307 (6)	0.0299 (6)	−0.0083 (5)	−0.0031 (5)	−0.0014 (4)
O4	0.0470 (7)	0.0484 (7)	0.0329 (6)	−0.0027 (5)	−0.0181 (5)	−0.0132 (5)
O5	0.0535 (7)	0.0332 (6)	0.0390 (6)	−0.0195 (5)	−0.0118 (5)	−0.0013 (5)
N1	0.0456 (8)	0.0279 (7)	0.0355 (7)	−0.0150 (6)	−0.0226 (6)	0.0018 (5)
C2	0.0348 (8)	0.0299 (7)	0.0302 (7)	−0.0130 (6)	−0.0154 (6)	0.0031 (6)
C3	0.0261 (7)	0.0362 (8)	0.0252 (7)	−0.0107 (6)	−0.0089 (5)	−0.0007 (6)
C4	0.0228 (7)	0.0319 (7)	0.0263 (7)	−0.0088 (6)	−0.0063 (5)	−0.0031 (6)
C5	0.0260 (7)	0.0290 (7)	0.0279 (7)	−0.0095 (6)	−0.0056 (6)	−0.0046 (6)
C6	0.0266 (7)	0.0313 (8)	0.0275 (7)	−0.0100 (6)	−0.0064 (6)	−0.0009 (6)
C7	0.0340 (8)	0.0353 (8)	0.0262 (7)	−0.0114 (6)	−0.0110 (6)	−0.0006 (6)
C8	0.0362 (8)	0.0306 (8)	0.0311 (8)	−0.0107 (6)	−0.0139 (6)	−0.0037 (6)
C9	0.0255 (7)	0.0296 (7)	0.0307 (7)	−0.0099 (6)	−0.0106 (6)	−0.0008 (6)
C10	0.0230 (7)	0.0307 (7)	0.0262 (7)	−0.0084 (6)	−0.0072 (5)	−0.0027 (6)
C11	0.0557 (11)	0.0401 (9)	0.0442 (9)	−0.0261 (8)	−0.0266 (8)	0.0126 (7)
C12	0.0389 (8)	0.0268 (7)	0.0292 (7)	−0.0073 (6)	−0.0129 (6)	0.0000 (6)
C13	0.0283 (9)	0.0824 (15)	0.0514 (11)	−0.0004 (9)	−0.0117 (8)	−0.0047 (10)
C14	0.0267 (7)	0.0353 (8)	0.0251 (7)	−0.0123 (6)	−0.0041 (5)	−0.0018 (6)
C15	0.0625 (12)	0.0587 (12)	0.0347 (9)	−0.0097 (10)	−0.0152 (8)	−0.0184 (8)
C16	0.0276 (7)	0.0323 (8)	0.0305 (8)	−0.0106 (6)	−0.0041 (6)	−0.0011 (6)
C17	0.0533 (10)	0.0393 (9)	0.0383 (9)	−0.0188 (8)	−0.0171 (8)	0.0095 (7)

Geometric parameters (Å, º) top

O1—C12	1.196 (2)	C7—H7	0.9300
O2—C12	1.3287 (19)	C8—C7	1.376 (2)
O2—C13	1.447 (2)	C8—H8	0.9300
O3—C14	1.2063 (19)	C9—C8	1.403 (2)
O4—C14	1.3401 (19)	C10—C4	1.474 (2)
O4—C15	1.4476 (19)	C10—C5	1.387 (2)
O5—C16	1.2211 (19)	C10—C9	1.422 (2)
N1—C2	1.4540 (19)	C11—H11A	0.9600
N1—C9	1.372 (2)	C11—H11B	0.9600
N1—H1	0.85 (2)	C11—H11C	0.9600
C2—C11	1.531 (2)	C13—H13A	0.9600
C2—C12	1.543 (2)	C13—H13B	0.9600
C3—C2	1.505 (2)	C13—H13C	0.9600
C3—C4	1.336 (2)	C15—H15A	0.9600
C3—H3	0.9300	C15—H15B	0.9600
C4—C14	1.496 (2)	C15—H15C	0.9600
C5—C6	1.402 (2)	C16—C17	1.509 (2)
C5—H5	0.9300	C17—H17A	0.9600
C6—C7	1.404 (2)	C17—H17B	0.9600
C6—C16	1.482 (2)	C17—H17C	0.9600

C12—O2—C13	116.35 (13)	C9—C10—C4	116.55 (13)
C14—O4—C15	116.25 (14)	C2—C11—H11A	109.5
C2—N1—H1	117.4 (13)	C2—C11—H11B	109.5
C9—N1—C2	120.53 (12)	C2—C11—H11C	109.5
C9—N1—H1	116.4 (13)	H11A—C11—H11B	109.5
N1—C2—C3	108.66 (12)	H11A—C11—H11C	109.5
N1—C2—C11	109.05 (12)	H11B—C11—H11C	109.5
N1—C2—C12	110.27 (12)	O1—C12—O2	124.00 (15)
C3—C2—C11	111.68 (13)	O1—C12—C2	124.45 (14)
C3—C2—C12	110.74 (11)	O2—C12—C2	111.53 (12)
C11—C2—C12	106.42 (13)	O2—C13—H13A	109.5
C2—C3—H3	119.0	O2—C13—H13B	109.5
C4—C3—C2	122.03 (13)	O2—C13—H13C	109.5
C4—C3—H3	119.0	H13A—C13—H13B	109.5
C3—C4—C10	120.21 (13)	H13A—C13—H13C	109.5
C3—C4—C14	119.01 (13)	H13B—C13—H13C	109.5
C10—C4—C14	120.62 (13)	O3—C14—O4	123.01 (14)
C6—C5—H5	119.0	O3—C14—C4	125.35 (14)
C10—C5—C6	121.90 (13)	O4—C14—C4	111.64 (13)
C10—C5—H5	119.0	O4—C15—H15A	109.5
C5—C6—C7	118.37 (13)	O4—C15—H15B	109.5
C5—C6—C16	118.55 (13)	O4—C15—H15C	109.5
C7—C6—C16	123.08 (13)	H15A—C15—H15B	109.5
C6—C7—H7	119.5	H15A—C15—H15C	109.5
C8—C7—C6	121.02 (13)	H15B—C15—H15C	109.5
C8—C7—H7	119.5	O5—C16—C6	120.92 (14)
C7—C8—C9	120.37 (13)	O5—C16—C17	119.68 (14)
C7—C8—H8	119.8	C6—C16—C17	119.41 (13)
C9—C8—H8	119.8	C16—C17—H17A	109.5
N1—C9—C8	120.72 (13)	C16—C17—H17B	109.5
N1—C9—C10	119.52 (13)	H17A—C17—H17B	109.5
C8—C9—C10	119.69 (13)	C16—C17—H17C	109.5
C5—C10—C4	124.87 (13)	H17A—C17—H17C	109.5
C5—C10—C9	118.57 (13)	H17B—C17—H17C	109.5

C13—O2—C12—O1	−2.3 (3)	C10—C4—C14—O4	−159.98 (12)
C13—O2—C12—C2	176.23 (15)	C10—C5—C6—C7	1.0 (2)
C15—O4—C14—O3	3.7 (2)	C10—C5—C6—C16	−179.06 (13)
C15—O4—C14—C4	−176.03 (14)	C5—C6—C7—C8	−2.2 (2)
C9—N1—C2—C3	41.36 (19)	C16—C6—C7—C8	177.88 (14)
C9—N1—C2—C11	163.31 (14)	C5—C6—C16—O5	6.5 (2)
C9—N1—C2—C12	−80.19 (17)	C5—C6—C16—C17	−173.14 (13)
C2—N1—C9—C8	154.73 (14)	C7—C6—C16—O5	−173.48 (14)
C2—N1—C9—C10	−28.4 (2)	C7—C6—C16—C17	6.8 (2)
N1—C2—C12—O1	−33.1 (2)	C9—C8—C7—C6	0.7 (2)
N1—C2—C12—O2	148.35 (13)	N1—C9—C8—C7	178.80 (14)
C3—C2—C12—O1	−153.45 (17)	C10—C9—C8—C7	2.0 (2)
C3—C2—C12—O2	28.05 (17)	C5—C10—C4—C3	−167.68 (14)
C11—C2—C12—O1	85.0 (2)	C5—C10—C4—C14	17.1 (2)
C11—C2—C12—O2	−93.51 (15)	C9—C10—C4—C3	13.5 (2)
C4—C3—C2—N1	−28.33 (19)	C9—C10—C4—C14	−161.74 (13)
C4—C3—C2—C11	−148.66 (14)	C4—C10—C5—C6	−177.15 (13)
C4—C3—C2—C12	92.93 (16)	C9—C10—C5—C6	1.6 (2)
C2—C3—C4—C10	2.8 (2)	C4—C10—C9—N1	−1.1 (2)
C2—C3—C4—C14	178.09 (12)	C4—C10—C9—C8	175.78 (12)
C3—C4—C14—O3	−155.01 (15)	C5—C10—C9—N1	−179.95 (13)
C3—C4—C14—O4	24.69 (19)	C5—C10—C9—C8	−3.1 (2)
C10—C4—C14—O3	20.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O5ⁱ	0.85 (2)	2.10 (2)	2.9223 (19)	166 (2)

Symmetry code: (i) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₇NO₅
M_r	303.31
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	7.9853 (7), 8.3950 (7), 12.4416 (11)
α, β, γ (°)	89.308 (7), 74.436 (7), 71.568 (7)
V (Å³)	759.82 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.36 × 0.34 × 0.31

Data collection
Diffractometer	Stoe IPDS II two-circle diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	12439, 2833, 2507
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.121, 1.05
No. of reflections	2833
No. of parameters	207
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.22

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), 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
N1—H1···O5ⁱ	0.85 (2)	2.10 (2)	2.9223 (19)	166 (2)

Symmetry code: (i) x, y−1, z.

Acknowledgements

The title compound was synthesized at RWTH Aachen University. The authors thank Professor Magnus Rueping of RWTH Aachen University, Germany, for helpful discussions.

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