8-Phenyl-3,4,6,7,8,8a-hexahydro-1H-pyrrolo­[2,1-c][1,4]oxazin-6-one

MałeckA, M.; Pasternak, B.; Leśniak, S.

doi:10.1107/S1600536811032806

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2390

doi:10.1107/S1600536811032806

Open

access

8-Phenyl-3,4,6,7,8,8a-hexahydro-1H-pyrrolo[2,1-c][1,4]oxazin-6-one

Magdalena Małecka,^a ^* Beata Pasternak ^b and Stanisław Leśniak ^b

^aDepartment of Structural Chemistry and Crystallography, University of Łódź, Tamka 12, PL-91403 Łódź, Poland, and ^bDepartment of Organic and Applied Chemistry, University of Łódź, Tamka 12, PL-91403 Łódź, Poland
^*Correspondence e-mail: malecka@uni.lodz.pl

(Received 19 July 2011; accepted 12 August 2011; online 27 August 2011)

In the title compound, C₁₃H₁₅NO₂, the hexahydropyrrolo[2,1-c][1,4]oxazine fragment is disordered over two conformations (A and B) in a 0.656 (5):0.344 (5) ratio. The five-membered ring is similarly disordered and adopts an envelope conformation in A, while in B this ring is nearly planar [maximum deviation = 0.088 (1) Å]. The six-membered rings in both A and B exhibit chair conformations. In the crystal, weak intermolecular C—H⋯O hydrogen bonds link the molecules into ribbons propagating in [010].

Related literature

For the synthesis, see: Leśniak et al. (2009 ). For bond-length data, see: Allen et al. (1987 ). For the biological properties of similar structures, see: Nicolaou et al. (2002 ). For related structures, see: Chaume et al. (2008 ); Dorsey et al. (2003 ); Harwood et al. (1997 ).

Experimental

Crystal data

C₁₃H₁₅NO₂
M_r = 217.27
Monoclinic, P 2₁ /c
a = 13.2737 (12) Å
b = 7.1066 (4) Å
c = 11.9233 (10) Å
β = 103.917 (7)°
V = 1091.72 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.36 × 0.21 × 0.03 mm

Data collection

Stoe IPDS 2 diffractometer
6960 measured reflections
2301 independent reflections
1200 reflections with I > 2σ(I)
R_int = 0.108

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.109
S = 0.81
2301 reflections
196 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 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
C2—H2B⋯O2ⁱ	0.97	2.46	3.329 (3)	149
C7A—H7A⋯O1ⁱⁱ	0.97	2.43	3.154 (4)	131
Symmetry codes: (i) x, y-1, z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: X-AREA (Stoe & Cie, 2000 ); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811032806/cv5138sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811032806/cv5138Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811032806/cv5138Isup3.cml

checkCIF report

Comment top

In this paper we provide a new oxazin-6-on derivative prepared in one step synthesis in FVT (Leśniak et al., 2009). The title compound (Fig. 1) represents an important structural unit found in biologically active compounds (Nicolaou et al., 2002). The hexahydro-pyrrolo[2,1-c][1,4] oxazine fragment is disordered over two conformations - A and B, respectively - in a ratio 0.656 (5):0.344 (5). Disordered five-membered ring adopts an envelope conformation in A, while in B this ring is nearly planar. Six-membered ring in A and B exhibits a chair conformation. Bond lengths (Allen et al., 1987) and angles are normal and correspond well to those observed in related structures (Chaume et al., 2008; Dorsey et al., 2003; Harwood et al., 1997).

The packing of the molecules in the crystal lattice is stabilized via weak intermolecular C—H···O hydrogen bonds (Table 1), which link the molecules into ribbons propagated in [010].

Related literature top

For the synthesis, see: Leśniak et al. (2009). For bond-length data, see: Allen et al. (1987). For the biological properties of similar structures, see: Nicolaou et al. (2002). For related structures, see: Chaume et al. (2008); Dorsey et al. (2003); Harwood et al. (1997).

Experimental top

General procedure. The flash vacuum thermolysis reactions were carried out in a 30x2.5 cm electrically heated horizontally oriented quartz tube packed with quartz rings, at 1.5x10^-3 Torr. The synthetic precursor (E)-1-morpholin-4-yl-3-phenylprop-2-en-1-one (2 mmol) was slowly sublimed at 80–100°C from a flask held into thermolysis preheated to 950–1000°C. The product thereby obtain was collected in a CO₂ acetone trap. After thermolysis, the whole system was brought to atmospheric pressure, allowing slow warming up to room temperature and the products were dissolved in CHCl₃. The solvent was removed under reduced pressure and 8-phenyl-hexahydro- pyrrolo[2,1-c][1,4]oxazin-6-one was purified chromatographically on SiO₂ and recrystallized from the hexane/CH₂Cl₂ (1:1) mixture.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2000); cell refinement: X-AREA (Stoe & Cie, 2000); data reduction: X-RED (Stoe & Cie, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

Fig. 1. Molecular structure of I with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

8-Phenyl-3,4,6,7,8,8a-hexahydro-1H- pyrrolo[2,1-c][1,4]oxazin-6-one top

Crystal data top

C₁₃H₁₅NO₂	F(000) = 464
M_r = 217.27	D_x = 1.322 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2762 reflections
a = 13.2737 (12) Å	θ = 1.6–27.1°
b = 7.1066 (4) Å	µ = 0.09 mm⁻¹
c = 11.9233 (10) Å	T = 100 K
β = 103.917 (7)°	Plate, colourless
V = 1091.72 (15) Å³	0.36 × 0.21 × 0.03 mm
Z = 4

Data collection top

Stoe IPDS 2 diffractometer	1200 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	R_int = 0.108
Planar graphite monochromator	θ_max = 26.8°, θ_min = 1.6°
Detector resolution: 6.67 pixels mm^-1	h = −16→16
rotation method scans	k = −8→8
6960 measured reflections	l = −14→15
2301 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)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.109	w = 1/[σ²(F_o²) + (0.0509P)²] where P = (F_o² + 2F_c²)/3
S = 0.81	(Δ/σ)_max < 0.001
2301 reflections	Δρ_max = 0.21 e Å⁻³
196 parameters	Δρ_min = −0.27 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.047 (4)

Crystal data top

C₁₃H₁₅NO₂	V = 1091.72 (15) Å³
M_r = 217.27	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.2737 (12) Å	µ = 0.09 mm⁻¹
b = 7.1066 (4) Å	T = 100 K
c = 11.9233 (10) Å	0.36 × 0.21 × 0.03 mm
β = 103.917 (7)°

Data collection top

Stoe IPDS 2 diffractometer	1200 reflections with I > 2σ(I)
6960 measured reflections	R_int = 0.108
2301 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 0.81	Δρ_max = 0.21 e Å⁻³
2301 reflections	Δρ_min = −0.27 e Å⁻³
196 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	Occ. (<1)
C6A	0.6366 (3)	0.7343 (6)	0.8977 (3)	0.0425 (9)	0.656 (5)
H6A	0.6341	0.8221	0.8348	0.051*	0.656 (5)
H6B	0.5799	0.7624	0.9333	0.051*	0.656 (5)
C6B	0.6801 (6)	0.6628 (11)	0.8736 (5)	0.0464 (18)	0.344 (5)
H6C	0.7183	0.5561	0.8543	0.056*	0.344 (5)
H6D	0.6709	0.7541	0.8115	0.056*	0.344 (5)
C5A	0.7290 (3)	0.6480 (5)	1.0830 (3)	0.0409 (9)	0.656 (5)
H5A	0.6657	0.6814	1.1054	0.049*	0.656 (5)
H5B	0.7878	0.6762	1.1466	0.049*	0.656 (5)
C5B	0.7692 (5)	0.5623 (12)	1.0597 (6)	0.0437 (17)	0.344 (5)
H5C	0.7980	0.4684	1.0172	0.052*	0.344 (5)
H5D	0.8204	0.5922	1.1304	0.052*	0.344 (5)
C7A	0.6287 (3)	0.5338 (5)	0.8537 (3)	0.0410 (9)	0.656 (5)
H7A	0.5612	0.5128	0.8019	0.049*	0.656 (5)
H7B	0.6814	0.5110	0.8112	0.049*	0.656 (5)
C7B	0.5784 (6)	0.6015 (11)	0.8900 (6)	0.051 (2)	0.344 (5)
H7C	0.5428	0.7067	0.9152	0.061*	0.344 (5)
H7D	0.5356	0.5545	0.8178	0.061*	0.344 (5)
N1A	0.6434 (2)	0.4075 (4)	0.9511 (2)	0.0353 (7)	0.656 (5)
N1B	0.5961 (5)	0.4532 (9)	0.9771 (5)	0.0411 (15)	0.344 (5)
C4A	0.7283 (3)	0.4418 (5)	1.0511 (2)	0.0364 (9)	0.656 (5)
H4A	0.7948	0.4042	1.0360	0.044*	0.656 (5)
C4B	0.6714 (5)	0.4927 (9)	1.0858 (5)	0.0407 (18)	0.344 (5)
H4B	0.6440	0.5817	1.1339	0.049*	0.344 (5)
O1	0.52984 (10)	0.1832 (2)	0.86955 (11)	0.0594 (5)
O2	0.73644 (10)	0.7476 (2)	0.98285 (11)	0.0568 (4)
C36	0.81951 (14)	0.3636 (3)	1.33444 (16)	0.0453 (5)
H36	0.7745	0.4576	1.3464	0.054*
C2	0.64430 (14)	0.1486 (3)	1.06256 (15)	0.0448 (5)
H2B	0.6954	0.0592	1.0491	0.054*
H2A	0.5935	0.0820	1.0940	0.054*
C32	0.86314 (15)	0.1182 (3)	1.22000 (16)	0.0459 (5)
H32	0.8476	0.0445	1.1536	0.055*
C35	0.91025 (14)	0.3310 (3)	1.41661 (16)	0.0514 (6)
H35	0.9259	0.4034	1.4835	0.062*
C33	0.95397 (15)	0.0859 (3)	1.30222 (18)	0.0516 (6)
H33	0.9991	−0.0083	1.2908	0.062*
C34	0.97791 (15)	0.1928 (3)	1.40096 (17)	0.0523 (6)
H34	1.0392	0.1719	1.4566	0.063*
C3	0.69621 (18)	0.3034 (3)	1.14461 (17)	0.0513 (6)
C31	0.79475 (13)	0.2572 (3)	1.23386 (14)	0.0408 (5)
C1	0.59269 (15)	0.2476 (3)	0.95258 (16)	0.0505 (5)
H7	0.6478 (17)	0.348 (4)	1.1835 (19)	0.074 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C6A	0.0416 (19)	0.041 (2)	0.0405 (18)	0.0053 (17)	0.0014 (14)	0.0030 (16)
C6B	0.060 (5)	0.038 (4)	0.039 (4)	0.002 (4)	0.008 (3)	−0.004 (3)
C5A	0.0446 (19)	0.043 (2)	0.0316 (16)	0.0039 (16)	0.0017 (14)	0.0012 (15)
C5B	0.040 (4)	0.040 (5)	0.046 (4)	−0.001 (3)	0.002 (3)	0.002 (3)
C7A	0.0405 (18)	0.047 (2)	0.0323 (17)	0.0032 (16)	0.0021 (13)	0.0030 (16)
C7B	0.052 (4)	0.061 (5)	0.033 (3)	0.003 (4)	−0.004 (3)	0.009 (3)
N1A	0.0368 (15)	0.0380 (16)	0.0278 (14)	0.0003 (12)	0.0012 (12)	0.0004 (11)
N1B	0.041 (3)	0.051 (4)	0.027 (3)	−0.006 (3)	0.000 (2)	0.004 (2)
C4A	0.0326 (17)	0.041 (2)	0.0320 (16)	0.0001 (15)	0.0012 (13)	−0.0001 (14)
C4B	0.039 (4)	0.046 (4)	0.034 (3)	−0.001 (3)	0.003 (3)	−0.003 (3)
O1	0.0560 (8)	0.0739 (11)	0.0405 (8)	−0.0204 (8)	−0.0034 (7)	−0.0059 (7)
O2	0.0596 (8)	0.0651 (10)	0.0396 (8)	−0.0191 (7)	0.0001 (6)	0.0087 (7)
C36	0.0479 (10)	0.0486 (12)	0.0393 (11)	−0.0088 (9)	0.0103 (8)	−0.0029 (9)
C2	0.0427 (10)	0.0501 (12)	0.0392 (11)	−0.0101 (9)	0.0052 (8)	−0.0007 (9)
C32	0.0566 (12)	0.0460 (13)	0.0338 (10)	−0.0097 (9)	0.0082 (9)	−0.0034 (9)
C35	0.0500 (12)	0.0702 (16)	0.0325 (11)	−0.0172 (11)	0.0070 (9)	−0.0101 (10)
C33	0.0476 (11)	0.0527 (14)	0.0522 (13)	−0.0031 (9)	0.0073 (10)	0.0005 (11)
C34	0.0449 (11)	0.0690 (16)	0.0389 (11)	−0.0107 (11)	0.0019 (9)	0.0050 (11)
C3	0.0674 (14)	0.0440 (13)	0.0347 (11)	−0.0032 (10)	−0.0031 (10)	0.0024 (10)
C31	0.0493 (10)	0.0421 (11)	0.0287 (10)	−0.0098 (9)	0.0050 (8)	0.0019 (9)
C1	0.0506 (11)	0.0627 (15)	0.0345 (11)	−0.0167 (10)	0.0027 (9)	0.0008 (10)

Geometric parameters (Å, º) top

C6A—O2	1.466 (3)	N1B—C4B	1.461 (7)
C6A—C7A	1.513 (6)	N1B—C1	1.489 (7)
C6A—H6A	0.9700	C4A—C3	1.618 (4)
C6A—H6B	0.9700	C4A—H4A	0.9800
C6B—O2	1.466 (7)	C4B—C3	1.516 (6)
C6B—C7B	1.476 (12)	C4B—H4B	0.9800
C6B—H6C	0.9700	O1—C1	1.220 (2)
C6B—H6D	0.9700	C36—C35	1.377 (2)
C5A—O2	1.411 (3)	C36—C31	1.389 (3)
C5A—C4A	1.513 (5)	C36—H36	0.9300
C5A—H5A	0.9700	C2—C1	1.500 (3)
C5A—H5B	0.9700	C2—C3	1.522 (3)
C5B—C4B	1.491 (10)	C2—H2B	0.9700
C5B—O2	1.603 (7)	C2—H2A	0.9700
C5B—H5C	0.9700	C32—C33	1.378 (3)
C5B—H5D	0.9700	C32—C31	1.378 (3)
C7A—N1A	1.444 (4)	C32—H32	0.9300
C7A—H7A	0.9700	C35—C34	1.373 (3)
C7A—H7B	0.9700	C35—H35	0.9300
C7B—N1B	1.459 (8)	C33—C34	1.373 (3)
C7B—H7C	0.9700	C33—H33	0.9300
C7B—H7D	0.9700	C34—H34	0.9300
N1A—C1	1.324 (3)	C3—C31	1.511 (3)
N1A—C4A	1.450 (4)	C3—H7	0.93 (2)

O2—C6A—C7A	106.0 (3)	C5B—C4B—C3	106.7 (6)
O2—C6A—H6A	110.5	N1B—C4B—H4B	111.9
C7A—C6A—H6A	110.5	C5B—C4B—H4B	111.9
O2—C6A—H6B	110.5	C3—C4B—H4B	111.9
C7A—C6A—H6B	110.5	C5A—O2—C6B	114.9 (3)
H6A—C6A—H6B	108.7	C5A—O2—C6A	108.5 (2)
O2—C6B—C7B	106.9 (6)	C6B—O2—C6A	34.4 (3)
O2—C6B—H6C	110.3	C5A—O2—C5B	33.9 (3)
C7B—C6B—H6C	110.3	C6B—O2—C5B	100.4 (4)
O2—C6B—H6D	110.3	C6A—O2—C5B	114.8 (3)
C7B—C6B—H6D	110.3	C35—C36—C31	120.5 (2)
H6C—C6B—H6D	108.6	C35—C36—H36	119.8
O2—C5A—C4A	105.7 (3)	C31—C36—H36	119.7
O2—C5A—H5A	110.6	C1—C2—C3	105.31 (17)
C4A—C5A—H5A	110.6	C1—C2—H2B	110.7
O2—C5A—H5B	110.6	C3—C2—H2B	110.7
C4A—C5A—H5B	110.6	C1—C2—H2A	110.7
H5A—C5A—H5B	108.7	C3—C2—H2A	110.7
C4B—C5B—O2	105.2 (5)	H2B—C2—H2A	108.8
C4B—C5B—H5C	110.7	C33—C32—C31	121.53 (18)
O2—C5B—H5C	110.7	C33—C32—H32	119.2
C4B—C5B—H5D	110.7	C31—C32—H32	119.2
O2—C5B—H5D	110.7	C34—C35—C36	120.81 (19)
H5C—C5B—H5D	108.8	C34—C35—H35	119.6
N1A—C7A—C6A	108.7 (3)	C36—C35—H35	119.6
N1A—C7A—H7A	109.9	C34—C33—C32	120.0 (2)
C6A—C7A—H7A	109.9	C34—C33—H33	120.0
N1A—C7A—H7B	109.9	C32—C33—H33	120.0
C6A—C7A—H7B	109.9	C33—C34—C35	119.22 (18)
H7A—C7A—H7B	108.3	C33—C34—H34	120.4
N1B—C7B—C6B	108.1 (5)	C35—C34—H34	120.4
N1B—C7B—H7C	110.1	C31—C3—C4B	125.0 (3)
C6B—C7B—H7C	110.1	C31—C3—C2	118.49 (18)
N1B—C7B—H7D	110.1	C4B—C3—C2	109.2 (2)
C6B—C7B—H7D	110.1	C31—C3—C4A	106.91 (19)
H7C—C7B—H7D	108.4	C4B—C3—C4A	37.5 (2)
C1—N1A—C7A	125.0 (2)	C2—C3—C4A	98.62 (18)
C1—N1A—C4A	115.5 (2)	C31—C3—H7	107.8 (14)
C7A—N1A—C4A	119.0 (3)	C4B—C3—H7	80.2 (16)
C7B—N1B—C4B	116.9 (5)	C2—C3—H7	107.7 (15)
C7B—N1B—C1	125.3 (5)	C4A—C3—H7	117.6 (16)
C4B—N1B—C1	110.2 (4)	C32—C31—C36	117.90 (17)
N1A—C4A—C5A	109.0 (2)	C32—C31—C3	123.72 (17)
N1A—C4A—C3	100.6 (2)	C36—C31—C3	118.36 (19)
C5A—C4A—C3	113.8 (3)	O1—C1—N1A	124.2 (2)
N1A—C4A—H4A	111.0	O1—C1—N1B	120.7 (3)
C5A—C4A—H4A	111.0	N1A—C1—N1B	33.7 (2)
C3—C4A—H4A	111.0	O1—C1—C2	127.8 (2)
N1B—C4B—C5B	108.8 (5)	N1A—C1—C2	106.68 (17)
N1B—C4B—C3	105.4 (4)	N1B—C1—C2	107.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O2ⁱ	0.97	2.46	3.329 (3)	149
C7A—H7A···O1ⁱⁱ	0.97	2.43	3.154 (4)	131

Symmetry codes: (i) x, y−1, z; (ii) −x+1, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₅NO₂
M_r	217.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	13.2737 (12), 7.1066 (4), 11.9233 (10)
β (°)	103.917 (7)
V (Å³)	1091.72 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.36 × 0.21 × 0.03

Data collection
Diffractometer	Stoe IPDS 2 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6960, 2301, 1200
R_int	0.108
(sin θ/λ)_max (Å⁻¹)	0.634

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.109, 0.81
No. of reflections	2301
No. of parameters	196
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.27

Computer programs: X-AREA (Stoe & Cie, 2000), X-RED (Stoe & Cie, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···O2ⁱ	0.97	2.46	3.329 (3)	149
C7A—H7A···O1ⁱⁱ	0.97	2.43	3.154 (4)	131

Symmetry codes: (i) x, y−1, z; (ii) −x+1, y+1/2, −z+3/2.

Acknowledgements

Financial support from University of Łódź (grant No. 505/721/R to MM) is gratefully acknowledged. The authors thank Dr Klaus Harms from Philipps University in Marburg (Germany) for collecting the data.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L. O., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin. Trans. 2, pp. S1–S19. Google Scholar
Chaume, G., Van Severen, M. C., Ricard, L. & Brigaud, T. (2008). J. Fluorine Chem. 129, 1104–1109. CrossRef CAS Google Scholar
Dorsey, A. D., Barbarow, J. E. & Trauner, D. (2003). Org. Lett. 5, 3237–3239. CrossRef CAS Google Scholar
Harwood, L. M., Hamblett, G., Jimenez-Diaz, A. I. & Watkin, D. J. (1997). Synlett, pp. 935–938. CrossRef Google Scholar
Leśniak, S., Pasternak, B. & Nazarski, R. (2009). Tetrahedron, 65, 6364–6369. Google Scholar
Nicolaou, K. C., Baran, P. S., Zhong, Y. L. & Sugita, K. (2002). J. Am. Chem. Soc. 124, 2212–2220. CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie. (2000). X-AREA and X-RED. Stoe & Cie, Darmstadt, Germany. Google Scholar