2,5-Diphenyl-2,5,6,8-tetra­hydro-1,2,4-triazolo[3,4-c][1,4]oxazin-4-ium hexa­fluorido­phosphate

Wu, J.; Wei, S.; Liu, B.; Wang, W.; Lan, J.

doi:10.1107/S1600536808022599

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1602

doi:10.1107/S1600536808022599

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2,5-Diphenyl-2,5,6,8-tetrahydro-1,2,4-triazolo[3,4-c][1,4]oxazin-4-ium hexafluoridophosphate

Jie Wu,^a Siping Wei,^a Bo Liu,^a Wenhai Wang ^a and Jingbo Lan ^a ^*

^aKey Laboratory of Green Chemistry and Technology of the Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China
^*Correspondence e-mail: jingbolan@scu.edu.cn

(Received 2 June 2008; accepted 18 July 2008; online 26 July 2008)

The title compound, C₁₇H₁₆N₃O⁺·PF₆⁻, is a chiral bicyclic 1,2,4-triazolium salt. In the crystal packing, C—H⋯O and C—H⋯F hydrogen bonds and P—F⋯π contacts [4.078 (11)–4.163 (11) Å, involving the triazolium ring] play an important role in enhancing the stability of the crystal structure.

Related literature

For related literature, see: Enders & Kallfass (2002 ); Fisher et al. (2006 ); Kerr et al., (2002 ); Knight & Leeper (1998 ); Readde Alaniz & Rovis, (2005 ).

Experimental

Crystal data

C₁₇H₁₆N₃O⁺·PF₆⁻
M_r = 423.30
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.1706 (6) Å
b = 11.4642 (8) Å
c = 19.7716 (14) Å
V = 1852.0 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 297 (2) K
0.58 × 0.55 × 0.26 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.850, T_max = 0.961
10481 measured reflections
3632 independent reflections
3040 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.096
S = 1.20
3632 reflections
257 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.22 e Å⁻³
Absolute structure: Flack (1983 ), 1537 Friedel pairs
Flack parameter: 0.06 (10)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯F2ⁱ	0.98	2.48	3.318 (3)	143
C5—H5A⋯Oⁱⁱ	0.93 (2)	2.34 (2)	2.899 (3)	118 (2)
Symmetry codes: (i) x+1, y-1, z; (ii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808022599/rk2095sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808022599/rk2095Isup2.hkl

checkCIF report

Comment top

Recently, triazolium salts which can be used as the precursors of carbenes are widely used in asymmetric catalysis for the C—C bond formation reactions, such as benzoin reactions (Knight & Leeper, 1998; Enders & Kallfass, 2002), Stetter reactions (Kerr et al., 2002; Readde Alaniz & Rovis, 2005) and Diels–Alder reactions (Fisher et al., 2006) owing to of their good stability and excellent catalytic performance. Most researchs illuminate, that chiral bicyclic 1,2,4–triazole carbenes have excellent enantio–selectivity because they have many bulkier groups and show weaker nucleophility than thiazolium and imiazolium salts. The molecular structure of the title compound (Fig. 1) shows that N1—C5—N3 is typical conjugated fragment because both bonds length N1—C5 = 1.330 (3)Å and N3—C5 = 1.322 (3)Å are longer than double bond N2—C2 = 1.296 (3)Å, but shorter than other N—C bonds (1.366 (3)–1.481 (3)Å) . In intermolecular network, P—F···π(Cg1) interactions [4.078 (11)–4.163 (11)Å] are the main contributor to the interaction of neighboring layers and play an important part in the connection of the adjacent porous layers in the title crystal structure (Cg1 is the triazolium centroid). The interatomic C—H···O and C—H···F hydrogen bond are present - see Table.

Related literature top

For related literature, see: Enders & Kallfass (2002); Fisher et al. (2006); Kerr et al., (2002); Knight & Leeper (1998); Readde Alaniz & Rovis, (2005).

Experimental top

The title compound was prepared according to the method (Knight & Leeper, 1998; Enders & Kallfass, 2002). A solution of 5–ethoxy–3–phenyl–3,6–dihydro–2H–1,4–oxazine (prepared from (R)–2–amino–2–phenylethanol) as a colourless liquid was added dropwise to phenylhydrazine hydrochloride (1.44 g, 10 mmol) in methanol (3 ml). The mixture was then stirred for 30 min, followed by addition of triethyl orthoformate (7.4 g, 50 mmol). After being heated at 353 K for 10 h, the reaction mixture was cooled to room temperature and concentrated in vacuo. The resulting residue was purified by column chromatography on silica gel with elution with methanol and followed with anion exchange with ammonium hexafluorophosphate to afford the pure triazolium salt as a white solid in 70% yield. Colourless crystals suitable for X–ray analysis were obtained by slow evaporation of acetone solution. ¹H NMR (400 MHz, DMSO): δ 4.05–4.10 (m, 1H), 4.37–4.41 (m, 1H), 5.22 (dd, J = 16 Hz, 16 Hz, 1H), 5.78 (dd, J = 6.0 Hz, 6.0 Hz, 1H), 7.47–7.68 (m, 8H), 7.69–7.91 (m, 2H).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound with the atom numbering scheme. The displacement ellipsoids are drawn at 50% probability level. The H atoms are presented as a small spheres of arbitrary radius.

2,5-Diphenyl-2,5,6,8-tetrahydro-1,2,4-triazolo[3,4-c][1,4]oxazin-4-ium hexafluorophosphate top

Crystal data top

C₁₇H₁₆N₃O⁺·PF₆⁻	F(000) = 864
M_r = 423.30	D_x = 1.518 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4928 reflections
a = 8.1706 (6) Å	θ = 2.5–26.0°
b = 11.4642 (8) Å	µ = 0.22 mm⁻¹
c = 19.7716 (14) Å	T = 297 K
V = 1852.0 (2) Å³	Prism, colourless
Z = 4	0.58 × 0.55 × 0.26 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3632 independent reflections
Radiation source: Fine–focus sealed tube	3040 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→7
T_min = 0.850, T_max = 0.961	k = −14→11
10481 measured reflections	l = −24→22

Refinement top

Refinement on F²	Secondary atom site location: Difmap
Least-squares matrix: Full	Hydrogen site location: Geom
R[F² > 2σ(F²)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.096	w = 1/[σ²(F_o²) + (0.05P)²] where P = (F_o² + 2F_c²)/3
S = 1.20	(Δ/σ)_max = 0.001
3632 reflections	Δρ_max = 0.19 e Å⁻³
257 parameters	Δρ_min = −0.22 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1537 Friedel pairs
Primary atom site location: Direct	Absolute structure parameter: 0.06 (10)

Crystal data top

C₁₇H₁₆N₃O⁺·PF₆⁻	V = 1852.0 (2) Å³
M_r = 423.30	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.1706 (6) Å	µ = 0.22 mm⁻¹
b = 11.4642 (8) Å	T = 297 K
c = 19.7716 (14) Å	0.58 × 0.55 × 0.26 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3632 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3040 reflections with I > 2σ(I)
T_min = 0.850, T_max = 0.961	R_int = 0.024
10481 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.096	Δρ_max = 0.19 e Å⁻³
S = 1.20	Δρ_min = −0.22 e Å⁻³
3632 reflections	Absolute structure: Flack (1983), 1537 Friedel pairs
257 parameters	Absolute structure parameter: 0.06 (10)
0 restraints

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
P	0.32742 (6)	0.98825 (5)	0.80826 (3)	0.05508 (16)
F1	0.2154 (2)	0.87484 (13)	0.80330 (9)	0.0959 (5)
F2	0.2554 (2)	1.02909 (15)	0.73698 (7)	0.0886 (5)
F3	0.4387 (2)	1.10126 (14)	0.80938 (10)	0.0966 (5)
F4	0.4001 (2)	0.94705 (14)	0.87749 (8)	0.0933 (5)
F5	0.1857 (2)	1.05734 (14)	0.84539 (8)	0.0836 (4)
F6	0.4689 (2)	0.92073 (17)	0.76896 (9)	0.0978 (5)
O	0.9022 (2)	−0.21782 (15)	0.73641 (11)	0.0824 (5)
N1	0.8395 (2)	0.01208 (15)	0.75583 (9)	0.0519 (4)
N2	0.8073 (2)	−0.00577 (15)	0.86600 (9)	0.0584 (4)
N3	0.8078 (2)	0.10971 (15)	0.84664 (8)	0.0508 (4)
C1	0.8303 (4)	−0.19097 (19)	0.79941 (16)	0.0791 (7)
H1A	0.8925	−0.2275	0.8354	0.095*
H1B	0.7196	−0.2213	0.8009	0.095*
C2	0.8273 (3)	−0.06202 (18)	0.80973 (13)	0.0599 (5)
C3	0.8765 (3)	−0.02665 (18)	0.68603 (12)	0.0617 (6)
H3A	0.9952	−0.0221	0.6795	0.074*
C4	0.8266 (3)	−0.1550 (2)	0.68261 (15)	0.0753 (7)
H4A	0.7085	−0.1616	0.6862	0.090*
H4B	0.8599	−0.1878	0.6395	0.090*
C5	0.8292 (3)	0.11963 (19)	0.78062 (10)	0.0510 (5)
H5A	0.844 (3)	0.188 (2)	0.7561 (11)	0.059 (6)*
C6	0.7964 (3)	0.04596 (19)	0.63230 (11)	0.0605 (6)
C7	0.8786 (4)	0.0594 (3)	0.57130 (14)	0.0873 (8)
H7A	0.9832	0.0287	0.5661	0.105*
C8	0.8056 (6)	0.1181 (3)	0.51833 (15)	0.1075 (11)
H8A	0.8602	0.1250	0.4772	0.129*
C9	0.6547 (5)	0.1658 (3)	0.52585 (14)	0.0951 (10)
H9A	0.6065	0.2059	0.4902	0.114*
C10	0.5736 (4)	0.1547 (3)	0.58587 (13)	0.0860 (8)
H10A	0.4711	0.1887	0.5911	0.103*
C11	0.6421 (3)	0.0937 (2)	0.63886 (12)	0.0704 (6)
H11A	0.5843	0.0846	0.6790	0.085*
C12	0.7902 (3)	0.20118 (18)	0.89483 (9)	0.0519 (5)
C13	0.8528 (3)	0.1859 (2)	0.95942 (11)	0.0722 (7)
H13A	0.9029	0.1163	0.9718	0.087*
C14	0.8388 (4)	0.2766 (3)	1.00491 (13)	0.0846 (8)
H14A	0.8789	0.2676	1.0486	0.101*
C15	0.7666 (4)	0.3795 (3)	0.98659 (13)	0.0834 (8)
H15A	0.7596	0.4407	1.0173	0.100*
C16	0.7046 (4)	0.3918 (2)	0.92254 (13)	0.0809 (7)
H16A	0.6546	0.4616	0.9103	0.097*
C17	0.7151 (3)	0.3032 (2)	0.87617 (11)	0.0645 (6)
H17A	0.6721	0.3121	0.8329	0.077*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P	0.0415 (3)	0.0612 (3)	0.0625 (3)	0.0005 (2)	−0.0050 (2)	−0.0123 (3)
F1	0.0832 (11)	0.0722 (9)	0.1322 (14)	−0.0225 (8)	−0.0041 (11)	−0.0090 (9)
F2	0.0910 (11)	0.1006 (11)	0.0742 (9)	0.0102 (9)	−0.0220 (8)	−0.0057 (8)
F3	0.0760 (10)	0.0894 (10)	0.1245 (14)	−0.0297 (9)	−0.0093 (10)	−0.0098 (10)
F4	0.0994 (12)	0.1078 (11)	0.0726 (9)	0.0169 (11)	−0.0210 (9)	0.0051 (9)
F5	0.0677 (9)	0.0933 (10)	0.0897 (10)	0.0160 (8)	0.0122 (8)	−0.0164 (8)
F6	0.0666 (9)	0.1201 (13)	0.1066 (12)	0.0267 (10)	0.0073 (8)	−0.0301 (10)
O	0.0625 (10)	0.0646 (10)	0.1201 (15)	0.0171 (9)	−0.0086 (11)	−0.0158 (10)
N1	0.0419 (8)	0.0518 (9)	0.0620 (10)	−0.0072 (9)	0.0024 (7)	−0.0045 (8)
N2	0.0485 (9)	0.0588 (10)	0.0681 (11)	0.0013 (9)	0.0003 (8)	0.0165 (9)
N3	0.0426 (9)	0.0568 (10)	0.0530 (9)	−0.0043 (8)	−0.0002 (8)	0.0044 (8)
C1	0.0693 (15)	0.0540 (12)	0.114 (2)	0.0035 (12)	−0.0008 (17)	0.0067 (14)
C2	0.0417 (10)	0.0570 (11)	0.0810 (15)	0.0025 (10)	−0.0004 (12)	0.0044 (12)
C3	0.0431 (10)	0.0719 (13)	0.0700 (14)	−0.0055 (10)	0.0067 (10)	−0.0197 (12)
C4	0.0557 (13)	0.0661 (13)	0.1042 (19)	0.0062 (12)	−0.0074 (15)	−0.0231 (13)
C5	0.0440 (11)	0.0567 (12)	0.0523 (11)	−0.0105 (10)	0.0021 (9)	0.0015 (9)
C6	0.0557 (13)	0.0633 (13)	0.0627 (12)	−0.0137 (11)	0.0087 (11)	−0.0184 (10)
C7	0.0816 (18)	0.108 (2)	0.0727 (17)	−0.0112 (17)	0.0216 (14)	−0.0218 (16)
C8	0.129 (3)	0.129 (3)	0.0636 (17)	−0.027 (3)	0.025 (2)	−0.0089 (17)
C9	0.126 (3)	0.095 (2)	0.0642 (17)	−0.013 (2)	−0.0022 (18)	0.0077 (14)
C10	0.097 (2)	0.0837 (18)	0.0776 (17)	0.0105 (17)	−0.0036 (16)	0.0053 (14)
C11	0.0725 (16)	0.0786 (15)	0.0602 (13)	−0.0006 (13)	0.0087 (11)	−0.0010 (11)
C12	0.0444 (11)	0.0618 (12)	0.0496 (11)	−0.0096 (10)	0.0010 (8)	0.0024 (9)
C13	0.0699 (16)	0.0886 (17)	0.0582 (13)	−0.0045 (14)	−0.0140 (11)	0.0056 (12)
C14	0.0924 (19)	0.112 (2)	0.0488 (12)	−0.0255 (19)	−0.0122 (13)	−0.0047 (14)
C15	0.092 (2)	0.098 (2)	0.0610 (15)	−0.0213 (18)	0.0092 (13)	−0.0184 (14)
C16	0.091 (2)	0.0764 (16)	0.0754 (15)	0.0059 (16)	0.0039 (15)	−0.0108 (13)
C17	0.0713 (15)	0.0686 (13)	0.0535 (11)	0.0033 (12)	−0.0045 (11)	0.0017 (10)

Geometric parameters (Å, º) top

P—F4	1.5653 (15)	C5—H5A	0.93 (2)
P—F3	1.5829 (17)	C6—C11	1.380 (3)
P—F5	1.5834 (17)	C6—C7	1.389 (3)
P—F1	1.5931 (15)	C7—C8	1.380 (5)
P—F6	1.5935 (18)	C7—H7A	0.9300
P—F2	1.5975 (15)	C8—C9	1.357 (5)
O—C1	1.411 (3)	C8—H8A	0.9300
O—C4	1.425 (3)	C9—C10	1.365 (4)
N1—C5	1.330 (3)	C9—H9A	0.9300
N1—C2	1.366 (3)	C10—C11	1.378 (4)
N1—C3	1.481 (3)	C10—H10A	0.9300
N2—C2	1.296 (3)	C11—H11A	0.9300
N2—N3	1.378 (2)	C12—C17	1.371 (3)
N3—C5	1.322 (3)	C12—C13	1.387 (3)
N3—C12	1.424 (3)	C13—C14	1.379 (4)
C1—C2	1.493 (3)	C13—H13A	0.9300
C1—H1A	0.9700	C14—C15	1.368 (4)
C1—H1B	0.9700	C14—H14A	0.9300
C3—C6	1.500 (3)	C15—C16	1.371 (4)
C3—C4	1.528 (3)	C15—H15A	0.9300
C3—H3A	0.9800	C16—C17	1.371 (3)
C4—H4A	0.9700	C16—H16A	0.9300
C4—H4B	0.9700	C17—H17A	0.9300

F4—P—F3	90.95 (10)	C3—C4—H4B	109.7
F4—P—F5	91.32 (9)	H4A—C4—H4B	108.2
F3—P—F5	90.24 (10)	N3—C5—N1	107.02 (19)
F4—P—F1	91.47 (10)	N3—C5—H5A	127.2 (13)
F3—P—F1	177.27 (11)	N1—C5—H5A	125.6 (13)
F5—P—F1	90.95 (9)	C11—C6—C7	118.6 (3)
F4—P—F6	90.26 (10)	C11—C6—C3	123.5 (2)
F3—P—F6	89.29 (10)	C7—C6—C3	117.8 (2)
F5—P—F6	178.36 (10)	C8—C7—C6	120.3 (3)
F1—P—F6	89.45 (10)	C8—C7—H7A	119.9
F4—P—F2	179.08 (10)	C6—C7—H7A	119.9
F3—P—F2	89.10 (10)	C9—C8—C7	120.4 (3)
F5—P—F2	89.60 (9)	C9—C8—H8A	119.8
F1—P—F2	88.46 (10)	C7—C8—H8A	119.8
F6—P—F2	88.83 (9)	C8—C9—C10	119.9 (3)
C1—O—C4	111.6 (2)	C8—C9—H9A	120.0
C5—N1—C2	106.52 (18)	C10—C9—H9A	120.0
C5—N1—C3	129.38 (18)	C9—C10—C11	120.7 (3)
C2—N1—C3	123.73 (18)	C9—C10—H10A	119.6
C2—N2—N3	103.84 (17)	C11—C10—H10A	119.6
C5—N3—N2	110.93 (18)	C10—C11—C6	120.0 (3)
C5—N3—C12	127.64 (18)	C10—C11—H11A	120.0
N2—N3—C12	121.42 (16)	C6—C11—H11A	120.0
O—C1—C2	110.1 (2)	C17—C12—C13	121.4 (2)
O—C1—H1A	109.6	C17—C12—N3	119.56 (18)
C2—C1—H1A	109.6	C13—C12—N3	119.1 (2)
O—C1—H1B	109.6	C14—C13—C12	118.4 (2)
C2—C1—H1B	109.6	C14—C13—H13A	120.8
H1A—C1—H1B	108.2	C12—C13—H13A	120.8
N2—C2—N1	111.67 (18)	C15—C14—C13	120.9 (2)
N2—C2—C1	127.7 (2)	C15—C14—H14A	119.6
N1—C2—C1	120.5 (2)	C13—C14—H14A	119.6
N1—C3—C6	113.87 (18)	C14—C15—C16	119.5 (2)
N1—C3—C4	106.0 (2)	C14—C15—H15A	120.2
C6—C3—C4	112.76 (19)	C16—C15—H15A	120.2
N1—C3—H3A	108.0	C17—C16—C15	121.2 (3)
C6—C3—H3A	108.0	C17—C16—H16A	119.4
C4—C3—H3A	108.0	C15—C16—H16A	119.4
O—C4—C3	109.8 (2)	C16—C17—C12	118.7 (2)
O—C4—H4A	109.7	C16—C17—H17A	120.7
C3—C4—H4A	109.7	C12—C17—H17A	120.7
O—C4—H4B	109.7

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···F2ⁱ	0.98	2.48	3.318 (3)	143
C5—H5A···Oⁱⁱ	0.93 (2)	2.34 (2)	2.899 (3)	118 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₆N₃O⁺·PF₆⁻
M_r	423.30
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	297
a, b, c (Å)	8.1706 (6), 11.4642 (8), 19.7716 (14)
V (Å³)	1852.0 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.58 × 0.55 × 0.26

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.850, 0.961
No. of measured, independent and observed [I > 2σ(I)] reflections	10481, 3632, 3040
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.096, 1.20
No. of reflections	3632
No. of parameters	257
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.22
Absolute structure	Flack (1983), 1537 Friedel pairs
Absolute structure parameter	0.06 (10)

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···F2ⁱ	0.98	2.48	3.318 (3)	143
C5—H5A···Oⁱⁱ	0.93 (2)	2.34 (2)	2.899 (3)	118 (2)

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

Acknowledgements

The authors are grateful to the National Natural Science Foundation of China (grant No. 20602027) for financial support.

References

Enders, D. & Kallfass, U. (2002). Angew. Chem. Int. Ed. 41, 1743–1745. CrossRef CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Fisher, C., Smith, S. W., Powell, D. A. & Fu, G. C. (2006). J. Am. Chem. Soc., 128, 1472–1473. Web of Science PubMed Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Kerr, M. S., Alaniz, J. & Rovis, T. (2002). J. Am. Chem. Soc. 124, 10298–10299. Web of Science CrossRef PubMed CAS Google Scholar
Knight, R. L. & Leeper, F. J. (1998). J. Chem. Soc. Perkin Trans. 1, pp. 1891–893. Web of Science CrossRef Google Scholar
Readde Alaniz, J. & Rovis, T. (2005). J. Am. Chem. Soc. 1274, 6284–6289. Web of Science CSD CrossRef Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar

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Volume 64| Part 8| August 2008| Page o1602

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2,5-Di­phenyl-2,5,6,8-tetra­hydro-1,2,4-triazolo[3,4-c][1,4]oxazin-4-ium hexa­fluorido­phosphate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2,5-Diphenyl-2,5,6,8-tetrahydro-1,2,4-triazolo[3,4-c][1,4]oxazin-4-ium hexafluoridophosphate