2,5-Diphenyl-2,5,6,8-tetra-hydro-1,2,4-triazolo[3,4-c][1,4]oxazin-4-ium hexa-fluorido-phosphate.

The title compound, C(17)H(16)N(3)O(+)·PF(6) (-), 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 = 423.30

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.096

S = 1.20

3632 reflections

257 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.22 e Å−3

Absolute structure: Flack (1983 ▶), 1537 Friedel pairs

Flack parameter: 0.06 (10)

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 ▶).

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H16N3O+·PF6–	F000 = 864
Mr = 423.30	Dx = 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 = 2.5–26.0º
b = 11.4642 (8) Å	µ = 0.22 mm−1
c = 19.7716 (14) Å	T = 297 (2) K
V = 1852.0 (2) Å3	Prism, colourless
Z = 4	0.58 × 0.55 × 0.26 mm

Bruker SMART CCD area-detector diffractometer	3040 reflections with I > 2σ(I)
Monochromator: Graphite	Rint = 0.024
T = 297(2) K	θmax = 26.0º
φ and ω scans	θmin = 2.1º
Absorption correction: Multi-scan(SADABS; Sheldrick, 1996)	h = −10→7
Tmin = 0.850, Tmax = 0.961	k = −14→11
10481 measured reflections	l = −24→22
3632 independent reflections

Refinement on F2	Hydrogen site location: Geom
Least-squares matrix: Full	H atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.035	w = 1/[σ2(Fo2) + (0.05P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.096	(Δ/σ)max = 0.001
S = 1.20	Δρmax = 0.19 e Å−3
3632 reflections	Δρmin = −0.22 e Å−3
257 parameters	Extinction correction: None
Primary atom site location: Direct	Absolute structure: Flack (1983), 1537 Friedel pairs
Secondary atom site location: Difmap	Flack parameter: 0.06 (10)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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

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)

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) ; (ii) .