(E)-3-[4-(Benzo[d]oxazol-2-yl)styr­yl]-1-methyl­pyridin-1-ium hexa­fluorido­phosphate

Xu, H.-K.; Kong, L.; Li, F.

doi:10.1107/S2414314617017357

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 12| December 2017| x171735

https://doi.org/10.1107/S2414314617017357

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(E)-3-[4-(Benzo[d]oxazol-2-yl)styryl]-1-methylpyridin-1-ium hexafluoridophosphate

Hong-Kang Xu,^a,^b Lin Kong ^a,^b ^* and Fei Li ^a,^b

^aDepartment of Chemistry, Anhui University, Hefei 230601, People's Republic of China, and ^bKey Laboratory of Functional Inorganic Materials Chemistry, Hefei 230601, People's Republic of China
^*Correspondence e-mail: kong_lin2009@126.com

Edited by D.-J. Xu, Zhejiang University (Yuquan Campus), China (Received 18 August 2017; accepted 4 December 2017; online 8 December 2017)

In the cation of the title molecular salt, C₂₁H₁₇N₂O⁺·PF₆⁻, the pyridine ring and benzoxazole ring system are twisted with respect to the central benzene ring at dihedral angles of 23.75 (18) and 5.53 (16)°. In the crystal, the hexafluoridophosphate anion accepts a weak C—H⋯F hydrogen bond from the cation to form an ion-pair.

Keywords: crystal structure; benzoxazole derivative; hexafluoridophosphate; C—H⋯F hydrogen bond.

CCDC reference: 1535133

Structure description

In this study, we report the crystal structure of title salt (Fig. 1). In the cation, the benzoxazole ring system and the pyridine ring are twisted by 23.75 (18) and 5.53 (16)°, respectively, to the central benzene ring, similar to the values found in a related structure (Qu et al., 2008 ). In the crystal, the hexafluoridophosphate anion accepts a weak C—H⋯F hydrogen bond from the cation to form an ion-pair (Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18A⋯F6ⁱ	0.96	2.51	3.228 (7)	132
Symmetry code: (i) -x+2, -y, -z+1.

Figure 1
The molecular structure of the title salt with displacement ellipsoids drawn at the 50% probability level.

Synthesis and crystallization

To a solution of silver hexafluoridophosphate (0.17 g, 0.68 mmol) in acetonitrile was added (E)-3-[4-(benzo[d]oxazol-2-yl)styryl]-1-methylpyridin-1-ium iodide (0.3 g, 0.68 mmol). The mixture was refluxed for 4 h, then filtered and evaporated, and concentrated in vacuo to give a solid product. Yellow single crystals were obtained in a 15% yield by recrystallization from acetonitrile solution.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₁H₁₇N₂O⁺·PF₆⁻
M_r	458.33
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	296
a, b, c (Å)	6.717 (2), 8.155 (3), 19.936 (6)
α, β, γ (°)	85.032 (3), 85.188 (3), 65.893 (3)
V (Å³)	991.6 (5)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.21
Crystal size (mm)	0.25 × 0.2 × 0.18

Data collection
Diffractometer	Bruker SMART 1000
No. of measured, independent and observed [I > 2σ(I)] reflections	7021, 3442, 3035
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.080, 0.246, 1.08
No. of reflections	3442
No. of parameters	281
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.69, −0.59
Computer programs: SMART and SAINT (Bruker, 2001 ), SHELXTL (Sheldrick, 2008 ) and SHELXL2014 (Sheldrick, 2015 ).

Structural data

CCDC reference: 1535133

Crystal structure: contains datablocks I, gloobal. DOI: https://doi.org/10.1107/S2414314617017357/xu4032sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617017357/xu4032Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617017357/xu4032Isup3.cml

checkCIF report

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(E)-3-[4-(Benzo[d]oxazol-2-yl)styryl]-1-methylpyridin-1-ium hexafluoridophosphate top

Crystal data top

C₂₁H₁₇N₂O⁺·PF₆⁻	Z = 2
M_r = 458.33	F(000) = 468
Triclinic, P1	D_x = 1.535 Mg m⁻³
a = 6.717 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.155 (3) Å	Cell parameters from 4838 reflections
c = 19.936 (6) Å	θ = 2.7–27.0°
α = 85.032 (3)°	µ = 0.21 mm⁻¹
β = 85.188 (3)°	T = 296 K
γ = 65.893 (3)°	Block, yellow
V = 991.6 (5) Å³	0.25 × 0.2 × 0.18 mm

Data collection top

Bruker SMART 1000 diffractometer	R_int = 0.023
phi and ω scans	θ_max = 25.0°, θ_min = 2.1°
7021 measured reflections	h = −7→7
3442 independent reflections	k = −9→9
3035 reflections with I > 2σ(I)	l = −23→23

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.080	H-atom parameters constrained
wR(F²) = 0.246	w = 1/[σ²(F_o²) + (0.1562P)² + 0.6275P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
3442 reflections	Δρ_max = 0.69 e Å⁻³
281 parameters	Δρ_min = −0.59 e Å⁻³

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. All hydrogen atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H = 0.93–0.96 Å and U_iso(H) = 1.5U_eq(C) for the methyl H atoms and 1.2U_eq(C) for the others.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
P1	0.69074 (14)	0.22595 (11)	0.11548 (4)	0.0542 (4)
F2	0.7984 (6)	0.0467 (4)	0.15891 (17)	0.1251 (13)
F6	0.4733 (6)	0.1997 (5)	0.1158 (3)	0.181 (2)
F1	0.6114 (8)	0.3458 (6)	0.1756 (2)	0.1692 (19)
F3	0.9069 (5)	0.2535 (4)	0.1129 (3)	0.1514 (17)
F4	0.7680 (10)	0.1089 (6)	0.05329 (19)	0.179 (2)
F5	0.5907 (7)	0.4022 (5)	0.0697 (2)	0.1567 (17)
O1	0.2734 (4)	0.8061 (3)	0.46644 (12)	0.0638 (7)
C9	0.4846 (5)	0.7808 (4)	0.47330 (17)	0.0572 (8)
C17	1.3454 (6)	0.2823 (4)	0.82449 (18)	0.0585 (8)
H17	1.4452	0.2606	0.7876	0.070*
C7	0.5824 (5)	0.6955 (4)	0.53677 (17)	0.0556 (8)
N1	1.4199 (5)	0.2301 (4)	0.88659 (15)	0.0620 (8)
N2	0.5754 (4)	0.8382 (4)	0.42255 (14)	0.0596 (7)
C5	0.2272 (5)	0.8911 (5)	0.40320 (17)	0.0582 (8)
C16	1.1258 (5)	0.3669 (4)	0.81385 (17)	0.0560 (8)
C6	0.4113 (5)	0.9123 (5)	0.37623 (17)	0.0577 (8)
C14	0.8545 (6)	0.4733 (5)	0.72631 (19)	0.0648 (9)
H14	0.7538	0.4660	0.7601	0.078*
C12	0.7684 (5)	0.5421 (5)	0.65957 (18)	0.0594 (8)
C15	1.0544 (6)	0.4212 (5)	0.74411 (18)	0.0622 (9)
H15	1.1603	0.4179	0.7104	0.075*
C13	0.8911 (5)	0.5823 (5)	0.60598 (19)	0.0657 (9)
H13	1.0376	0.5565	0.6109	0.079*
C21	0.9837 (6)	0.3997 (5)	0.87051 (19)	0.0660 (9)
H21	0.8341	0.4599	0.8658	0.079*
C19	1.2841 (7)	0.2591 (5)	0.9406 (2)	0.0721 (10)
H19	1.3389	0.2221	0.9832	0.086*
C8	0.7991 (5)	0.6594 (5)	0.54604 (18)	0.0632 (9)
H8	0.8829	0.6877	0.5112	0.076*
C10	0.4596 (6)	0.6525 (6)	0.5896 (2)	0.0704 (10)
H10	0.3148	0.6738	0.5841	0.084*
C18	1.6587 (7)	0.1359 (7)	0.8941 (3)	0.0868 (13)
H18A	1.6944	0.0118	0.9079	0.130*
H18B	1.7015	0.1913	0.9275	0.130*
H18C	1.7347	0.1435	0.8518	0.130*
C1	0.4092 (7)	0.9970 (5)	0.31239 (19)	0.0694 (9)
H1	0.5319	1.0120	0.2929	0.083*
C11	0.5524 (6)	0.5786 (6)	0.6501 (2)	0.0739 (11)
H11	0.4679	0.5526	0.6853	0.089*
C2	0.2198 (7)	1.0570 (5)	0.2796 (2)	0.0743 (10)
H2	0.2129	1.1162	0.2372	0.089*
C20	1.0635 (7)	0.3432 (5)	0.9341 (2)	0.0751 (10)
H20	0.9680	0.3623	0.9720	0.090*
C3	0.0344 (7)	1.0318 (6)	0.3080 (2)	0.0779 (11)
H3	−0.0908	1.0731	0.2837	0.093*
C4	0.0342 (6)	0.9480 (6)	0.3705 (2)	0.0753 (11)
H4	−0.0871	0.9305	0.3898	0.090*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0594 (6)	0.0470 (5)	0.0577 (6)	−0.0233 (4)	−0.0063 (4)	0.0006 (4)
F2	0.175 (3)	0.086 (2)	0.124 (2)	−0.062 (2)	−0.068 (2)	0.0443 (18)
F6	0.094 (2)	0.118 (3)	0.355 (7)	−0.066 (2)	−0.030 (3)	−0.001 (4)
F1	0.225 (5)	0.161 (4)	0.140 (3)	−0.095 (3)	0.068 (3)	−0.092 (3)
F3	0.0738 (19)	0.096 (2)	0.289 (5)	−0.0416 (16)	−0.003 (2)	−0.006 (3)
F4	0.309 (6)	0.121 (3)	0.097 (2)	−0.070 (3)	−0.006 (3)	−0.041 (2)
F5	0.183 (4)	0.086 (2)	0.201 (4)	−0.054 (2)	−0.087 (3)	0.070 (3)
O1	0.0502 (12)	0.0778 (16)	0.0629 (14)	−0.0259 (11)	−0.0069 (10)	0.0024 (12)
C9	0.0510 (17)	0.0540 (18)	0.063 (2)	−0.0165 (14)	−0.0066 (14)	−0.0074 (15)
C17	0.064 (2)	0.0539 (18)	0.0607 (19)	−0.0261 (15)	−0.0076 (15)	−0.0032 (14)
C7	0.0501 (17)	0.0540 (17)	0.0595 (18)	−0.0172 (14)	−0.0041 (14)	−0.0053 (14)
N1	0.0731 (18)	0.0532 (15)	0.0662 (18)	−0.0300 (14)	−0.0190 (14)	0.0016 (13)
N2	0.0476 (14)	0.0661 (17)	0.0614 (16)	−0.0193 (12)	−0.0034 (12)	−0.0017 (13)
C5	0.0534 (18)	0.0600 (19)	0.0589 (18)	−0.0199 (14)	−0.0078 (14)	−0.0027 (15)
C16	0.0625 (19)	0.0443 (16)	0.0629 (19)	−0.0225 (14)	−0.0075 (15)	−0.0032 (13)
C6	0.0541 (18)	0.0572 (18)	0.0595 (18)	−0.0186 (14)	−0.0042 (14)	−0.0103 (14)
C14	0.064 (2)	0.067 (2)	0.063 (2)	−0.0269 (17)	−0.0055 (16)	−0.0005 (16)
C12	0.0570 (19)	0.0549 (18)	0.0617 (19)	−0.0178 (15)	−0.0045 (15)	−0.0024 (15)
C15	0.0570 (19)	0.0601 (19)	0.064 (2)	−0.0180 (15)	−0.0034 (15)	−0.0024 (16)
C13	0.0455 (17)	0.079 (2)	0.068 (2)	−0.0208 (16)	−0.0079 (15)	0.0000 (18)
C21	0.068 (2)	0.0565 (19)	0.073 (2)	−0.0241 (16)	−0.0030 (17)	−0.0057 (16)
C19	0.099 (3)	0.065 (2)	0.062 (2)	−0.042 (2)	−0.011 (2)	−0.0015 (17)
C8	0.0476 (17)	0.076 (2)	0.0596 (19)	−0.0200 (16)	0.0023 (14)	−0.0029 (16)
C10	0.0505 (18)	0.088 (3)	0.076 (2)	−0.0326 (18)	−0.0084 (16)	0.011 (2)
C18	0.073 (3)	0.091 (3)	0.100 (3)	−0.034 (2)	−0.035 (2)	0.008 (2)
C1	0.073 (2)	0.071 (2)	0.062 (2)	−0.0281 (18)	−0.0005 (17)	−0.0038 (17)
C11	0.062 (2)	0.093 (3)	0.072 (2)	−0.040 (2)	−0.0065 (17)	0.015 (2)
C2	0.087 (3)	0.070 (2)	0.059 (2)	−0.023 (2)	−0.0120 (18)	−0.0027 (17)
C20	0.093 (3)	0.069 (2)	0.068 (2)	−0.039 (2)	0.009 (2)	−0.0106 (18)
C3	0.070 (2)	0.089 (3)	0.069 (2)	−0.023 (2)	−0.0232 (19)	−0.003 (2)
C4	0.055 (2)	0.090 (3)	0.079 (3)	−0.0261 (19)	−0.0131 (17)	−0.002 (2)

Geometric parameters (Å, º) top

P1—F1	1.532 (3)	C14—H14	0.9300
P1—F4	1.552 (3)	C12—C11	1.383 (5)
P1—F3	1.553 (3)	C12—C13	1.393 (5)
P1—F6	1.559 (3)	C15—H15	0.9300
P1—F2	1.559 (3)	C13—C8	1.372 (5)
P1—F5	1.561 (3)	C13—H13	0.9300
O1—C9	1.364 (4)	C21—C20	1.385 (6)
O1—C5	1.380 (4)	C21—H21	0.9300
C9—N2	1.289 (4)	C19—C20	1.367 (6)
C9—C7	1.460 (5)	C19—H19	0.9300
C17—N1	1.343 (4)	C8—H8	0.9300
C17—C16	1.376 (5)	C10—C11	1.378 (5)
C17—H17	0.9300	C10—H10	0.9300
C7—C8	1.388 (5)	C18—H18A	0.9600
C7—C10	1.393 (5)	C18—H18B	0.9600
N1—C19	1.323 (5)	C18—H18C	0.9600
N1—C18	1.483 (5)	C1—C2	1.365 (6)
N2—C6	1.401 (4)	C1—H1	0.9300
C5—C6	1.376 (5)	C11—H11	0.9300
C5—C4	1.385 (5)	C2—C3	1.408 (6)
C16—C21	1.386 (5)	C2—H2	0.9300
C16—C15	1.480 (5)	C20—H20	0.9300
C6—C1	1.393 (5)	C3—C4	1.370 (6)
C14—C15	1.303 (5)	C3—H3	0.9300
C14—C12	1.468 (5)	C4—H4	0.9300

F1—P1—F4	178.5 (3)	C13—C12—C14	122.9 (3)
F1—P1—F3	88.0 (3)	C14—C15—C16	125.0 (3)
F4—P1—F3	92.1 (3)	C14—C15—H15	117.5
F1—P1—F6	93.1 (3)	C16—C15—H15	117.5
F4—P1—F6	86.8 (3)	C8—C13—C12	121.0 (3)
F3—P1—F6	178.3 (3)	C8—C13—H13	119.5
F1—P1—F2	95.1 (3)	C12—C13—H13	119.5
F4—P1—F2	86.4 (2)	C20—C21—C16	120.3 (4)
F3—P1—F2	90.0 (2)	C20—C21—H21	119.8
F6—P1—F2	91.2 (2)	C16—C21—H21	119.8
F1—P1—F5	86.8 (3)	N1—C19—C20	120.3 (4)
F4—P1—F5	91.7 (3)	N1—C19—H19	119.9
F3—P1—F5	88.7 (2)	C20—C19—H19	119.9
F6—P1—F5	90.1 (2)	C13—C8—C7	120.7 (3)
F2—P1—F5	177.6 (2)	C13—C8—H8	119.6
C9—O1—C5	103.8 (3)	C7—C8—H8	119.6
N2—C9—O1	115.6 (3)	C11—C10—C7	120.1 (3)
N2—C9—C7	127.0 (3)	C11—C10—H10	120.0
O1—C9—C7	117.4 (3)	C7—C10—H10	120.0
N1—C17—C16	121.9 (3)	N1—C18—H18A	109.5
N1—C17—H17	119.0	N1—C18—H18B	109.5
C16—C17—H17	119.0	H18A—C18—H18B	109.5
C8—C7—C10	118.7 (3)	N1—C18—H18C	109.5
C8—C7—C9	120.4 (3)	H18A—C18—H18C	109.5
C10—C7—C9	120.9 (3)	H18B—C18—H18C	109.5
C19—N1—C17	121.2 (3)	C2—C1—C6	117.2 (4)
C19—N1—C18	119.9 (3)	C2—C1—H1	121.4
C17—N1—C18	119.0 (3)	C6—C1—H1	121.4
C9—N2—C6	104.1 (3)	C10—C11—C12	121.4 (3)
C6—C5—O1	107.6 (3)	C10—C11—H11	119.3
C6—C5—C4	124.1 (4)	C12—C11—H11	119.3
O1—C5—C4	128.3 (3)	C1—C2—C3	121.9 (4)
C17—C16—C21	116.9 (3)	C1—C2—H2	119.1
C17—C16—C15	119.3 (3)	C3—C2—H2	119.1
C21—C16—C15	123.8 (3)	C19—C20—C21	119.4 (4)
C5—C6—C1	119.8 (3)	C19—C20—H20	120.3
C5—C6—N2	108.8 (3)	C21—C20—H20	120.3
C1—C6—N2	131.4 (3)	C4—C3—C2	121.6 (4)
C15—C14—C12	128.1 (4)	C4—C3—H3	119.2
C15—C14—H14	115.9	C2—C3—H3	119.2
C12—C14—H14	115.9	C3—C4—C5	115.4 (4)
C11—C12—C13	118.1 (3)	C3—C4—H4	122.3
C11—C12—C14	118.9 (3)	C5—C4—H4	122.3

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18A···F6ⁱ	0.96	2.51	3.228 (7)	132

Symmetry code: (i) −x+2, −y, −z+1.

Funding information

This work was supported by the Graduate Students Innovative Program of Anhui University, China (J18515024, J18515019, 201310357155).

References

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