1,3-Bis[(5-amino­furan-2-yl)meth­yl]-3,4,5,6-tetra­hydro­pyrimidin-1-ium hexa­fluoro­phosphate

Akkurt, M.; Akkoç, S.; Gök, Y.; Tahir, M.N.

doi:10.1107/S1600536813020187

organic compounds

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ISSN: 2056-9890

Volume 69| Part 8| August 2013| Page o1325

doi:10.1107/S1600536813020187

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1,3-Bis[(5-aminofuran-2-yl)methyl]-3,4,5,6-tetrahydropyrimidin-1-ium hexafluorophosphate

Mehmet Akkurt,^a Senem Akkoç,^b Yetkin Gök ^c and Muhammad Nawaz Tahir ^d ^*

^aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^bDepartment of Chemistry, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^cDepartment of Chemistry, Faculty of Arts and Sciences, Inönü University, 44280, Malatya, Turkey, and ^dDepartment of Physics, University of Sargodha, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 18 July 2013; accepted 22 July 2013; online 27 July 2013)

The asymmetric unit of the title salt, C₁₆H₂₁N₂O₂⁺·PF₆⁻, contains half of the whole ion pair, which has crystallographic mirror symmetry. Two F atoms related by the mirror plane are disordered over two sites of equal occupancy. The dihedral angle between the central ring and the furan ring is 59.3 ()°. In the crystal, the anions and cations are linked through C—H⋯F interactions, forming a three-dimensional network.

Related literature

N-heterocyclic carbene (NHC)-metal complexes have attracted much attention, particularly for their functions in catalytic reactions, see: Akkoç & Gök (2013 ); Arduengo et al. (1992 ); Bagherzadeh et al. (2012 ); Hermann (2002 ); Lee et al. (2013 ); Saba et al. (1991 ); Yiğit et al. (2007 ); Özdemir et al. (2001 ); Çetinkaya et al. (1997 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₆H₂₁N₂O₂⁺·PF₆⁻
M_r = 418.32
Monoclinic, P 2₁ /m
a = 6.0793 (6) Å
b = 18.879 (2) Å
c = 8.5750 (9) Å
β = 100.747 (5)°
V = 966.90 (17) Å³
Z = 2
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 296 K
0.35 × 0.28 × 0.23 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: part of the refinement model (ΔF) (XABS2; Parkin et al., 1995 ) T_min = 0.932, T_max = 0.953
1677 measured reflections
1677 independent reflections
1089 reflections with I > 2σ(I)
R_int = 0.000

Refinement

R[F² > 2σ(F²)] = 0.077
wR(F²) = 0.247
S = 1.08
1677 reflections
144 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.55 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯F2ⁱ	0.93	2.40	3.312 (8)	167
C1—H1⋯F4ⁱⁱ	0.93	2.52	3.044 (8)	116
Symmetry codes: (i) x, y, z-1; (ii) x-1, y, z-1.

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); 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 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813020187/hg5332sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813020187/hg5332Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813020187/hg5332Isup3.cml

checkCIF report

Comment top

1,3-Di(5-methylfurfuryl)pyrimidinium hexafluorophosphate salt is conventional N-heterocyclic carbene (NHC) precursors. N-heterocyclic carbenes (NHCs) are generally considered as analogues of phosphine ligands because of their good s-donating but very weak p-accepting ability (Arduengo et al., 1992). Normally, NHC-metal complexes have higher stability toward heat, moisture, and oxygen than phosphine metal based complexes, which makes them quite attractive as phosphine substitute. In recent years, NHCs are fully used as organocatalysts and ancillary ligands in transition metal catalyzed reactions (Hermann, 2002). They have attracted many attention, particularly for its functions in catalytic reactions (Akkoç & Gök, 2013; Lee et al., 2013; Bagherzadeh et al., 2012; Çetinkaya et al., 1997; Özdemir et al., 2001; Saba et al., 1991; Yiğit et al., 2007).

Fig. 1 shows the whole molecule (I) whose anions and cations form two parts with a crystallographic mirror symmetry. The C1–N1–C2–C3, C1–N1–C4–C5, C2–N1–C4–C5, N1–C4–C5–O1 and N1–C4–C5–C6 torsion angles are -25.1 (6), -121.5 (4), 60.4 (5), -85.1 (4) and 96.4 (6) °, respectively. All bond lengths of (I) are within normal values (Allen et al., 1987).

The crystal structure is stabilized by C—H···F interactions between the anions and cations of (I), forming a three dimensional network (Table 1, Figures 2 and 3).

Related literature top

N-heterocyclic carbene (NHC)-metal complexes have attracted much attention, particularly for their functions in catalytic reactions, see: Akkoç & Gök (2013); Arduengo et al. (1992); Bagherzadeh et al. (2012); Hermann (2002); Lee et al. (2013); Saba et al. (1991); Yiğit et al. (2007); Özdemir et al. (2001); Çetinkaya et al. (1997). For bond-length data, see: Allen et al. (1987).

Experimental top

The reaction for the preparation of heterocyclic salt containing furan moiety was carried out under argon in flame dried glassware using standard Schlenk type flasks. The synthesis of salt containing furan moiety was achieved by the reaction of N,N'-dialkylpropane-1,3-diamine (1.0 mmol) with ammonium hexafluorophosphate (1.0 mmol) in triethyl orthoformate (5 ml) (Scheme 1). The reaction mixture was heated for 12 h at 353 K. A white solid was precipitated. The precipitation was then crystallized from Et₂O/EtOH (2:1) at room temperature. The resulting 1,3-di(5-methylfurfuryl)pyrimidinium hexafluorophosphate salt was obtained in good yield.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title compound with a crystallographic mirror symmetry. Displacement ellipsoids are shown at the 20% probability levels. The disordered F5, F6 and F5a, F5b atoms are related to each other with a mirror symmetry operation. Symmetry codes: (a) x, 1/2 - y, z; (b) x, 1/2 - y, z.
	Fig. 2. View of the crystal packing and the hydrogen bonding of (I) along a axis. H atoms not involved in hydrogen bonding are omitted for clarity.
	Fig. 3. View of the crystal packing and the hydrogen bonding of (I) along c axis. H atoms not involved in hydrogen bonding are omitted for clarity.

1,3-Bis[(5-aminofuran-2-yl)methyl]-3,4,5,6-tetrahydropyrimidin-1-ium hexafluorophosphate top

Crystal data top

C₁₆H₂₁N₂O₂⁺·PF₆⁻	F(000) = 432
M_r = 418.32	D_x = 1.437 Mg m⁻³
Monoclinic, P2₁/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yb	Cell parameters from 1100 reflections
a = 6.0793 (6) Å	θ = 2.5–25°
b = 18.879 (2) Å	µ = 0.21 mm⁻¹
c = 8.5750 (9) Å	T = 296 K
β = 100.747 (5)°	Prism, colourless
V = 966.90 (17) Å³	0.35 × 0.28 × 0.23 mm
Z = 2

Data collection top

Bruker Kappa APEXII CCD diffractometer	1677 independent reflections
Radiation source: fine-focus sealed tube	1089 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.000
ω scans	θ_max = 24.7°, θ_min = 2.2°
Absorption correction: part of the refinement model (ΔF) (XABS2; Parkin et al., 1995)	h = −7→7
T_min = 0.932, T_max = 0.953	k = 0→22
1677 measured reflections	l = 0→10

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)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.247	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.1389P)² + 0.421P] where P = (F_o² + 2F_c²)/3
1677 reflections	(Δ/σ)_max < 0.001
144 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.55 e Å⁻³

Crystal data top

C₁₆H₂₁N₂O₂⁺·PF₆⁻	V = 966.90 (17) Å³
M_r = 418.32	Z = 2
Monoclinic, P2₁/m	Mo Kα radiation
a = 6.0793 (6) Å	µ = 0.21 mm⁻¹
b = 18.879 (2) Å	T = 296 K
c = 8.5750 (9) Å	0.35 × 0.28 × 0.23 mm
β = 100.747 (5)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	1677 independent reflections
Absorption correction: part of the refinement model (ΔF) (XABS2; Parkin et al., 1995)	1089 reflections with I > 2σ(I)
T_min = 0.932, T_max = 0.953	R_int = 0.000
1677 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.077	0 restraints
wR(F²) = 0.247	H-atom parameters constrained
S = 1.08	Δρ_max = 0.36 e Å⁻³
1677 reflections	Δρ_min = −0.55 e Å⁻³
144 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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)
O1	0.0509 (5)	0.46898 (16)	0.2298 (3)	0.0808 (11)
N1	−0.1021 (5)	0.31127 (19)	0.1262 (4)	0.0706 (11)
C1	−0.0850 (8)	0.25000	0.0606 (6)	0.069 (2)
C2	−0.1511 (9)	0.3154 (3)	0.2862 (5)	0.0872 (17)
C3	−0.2709 (14)	0.25000	0.3206 (9)	0.106 (3)
C4	−0.0792 (7)	0.3771 (2)	0.0383 (5)	0.0817 (16)
C5	0.1016 (7)	0.4235 (2)	0.1168 (5)	0.0725 (16)
C6	0.3108 (8)	0.4325 (3)	0.1001 (6)	0.091 (2)
C7	0.4019 (9)	0.4871 (3)	0.2040 (6)	0.094 (2)
C8	0.2431 (9)	0.5075 (3)	0.2828 (5)	0.0852 (17)
C9	0.2247 (12)	0.5625 (3)	0.4039 (7)	0.120 (3)
P1	0.3506 (2)	0.25000	0.73427 (19)	0.0793 (7)
F1	0.3265 (10)	0.25000	0.5584 (6)	0.247 (6)
F2	0.0993 (9)	0.25000	0.7207 (8)	0.236 (6)
F3	0.3704 (10)	0.25000	0.9155 (7)	0.218 (5)
F4	0.6000 (9)	0.25000	0.7399 (8)	0.260 (7)
F5	0.449 (3)	0.3183 (5)	0.7947 (15)	0.204 (7)	0.500
F6	0.258 (3)	0.3213 (5)	0.699 (2)	0.260 (8)	0.500
H1	−0.05810	0.25000	−0.04260	0.0820*
H2A	−0.24330	0.35660	0.29500	0.1050*
H2B	−0.01270	0.32020	0.36270	0.1050*
H3A	−0.28490	0.25000	0.43150	0.1280*
H3B	−0.42050	0.25000	0.25680	0.1280*
H4A	−0.05180	0.36490	−0.06630	0.0980*
H4B	−0.21940	0.40290	0.02440	0.0980*
H6	0.38470	0.40730	0.03220	0.1090*
H7	0.54600	0.50550	0.21560	0.1130*
H9A	0.36010	0.58990	0.42480	0.1800*
H9B	0.20190	0.54010	0.50010	0.1800*
H9C	0.10040	0.59310	0.36490	0.1800*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0858 (19)	0.098 (2)	0.0648 (18)	0.0177 (16)	0.0303 (14)	0.0102 (15)
N1	0.070 (2)	0.094 (2)	0.0496 (19)	0.0089 (16)	0.0162 (14)	0.0031 (17)
C1	0.050 (3)	0.108 (5)	0.048 (3)	0.0000	0.008 (2)	0.0000
C2	0.104 (3)	0.107 (3)	0.057 (3)	0.013 (3)	0.032 (2)	0.000 (2)
C3	0.113 (5)	0.148 (7)	0.071 (4)	0.0000	0.052 (4)	0.0000
C4	0.085 (3)	0.102 (3)	0.058 (2)	0.027 (2)	0.013 (2)	0.014 (2)
C5	0.085 (3)	0.080 (3)	0.057 (2)	0.025 (2)	0.025 (2)	0.0179 (19)
C6	0.088 (3)	0.101 (4)	0.094 (4)	0.021 (2)	0.042 (3)	0.017 (3)
C7	0.087 (3)	0.102 (4)	0.098 (4)	−0.003 (3)	0.031 (3)	0.018 (3)
C8	0.105 (3)	0.086 (3)	0.067 (3)	0.005 (3)	0.022 (2)	0.020 (2)
C9	0.170 (6)	0.112 (4)	0.083 (4)	−0.004 (4)	0.039 (4)	0.000 (3)
P1	0.0552 (9)	0.1200 (15)	0.0645 (11)	0.0000	0.0157 (7)	0.0000
F1	0.104 (4)	0.578 (18)	0.065 (3)	0.0000	0.030 (3)	0.0000
F2	0.077 (3)	0.516 (17)	0.121 (5)	0.0000	0.036 (3)	0.0000
F3	0.111 (4)	0.449 (14)	0.094 (4)	0.0000	0.023 (3)	0.0000
F4	0.071 (3)	0.59 (2)	0.116 (5)	0.0000	0.012 (3)	0.0000
F5	0.291 (15)	0.108 (6)	0.199 (11)	−0.077 (8)	0.013 (10)	−0.036 (6)
F6	0.242 (13)	0.114 (7)	0.36 (2)	0.065 (7)	−0.111 (14)	0.018 (9)

Geometric parameters (Å, º) top

P1—F6ⁱ	1.469 (11)	C5—C6	1.317 (7)
P1—F1	1.488 (5)	C6—C7	1.407 (8)
P1—F2	1.510 (6)	C7—C8	1.334 (8)
P1—F3	1.536 (6)	C8—C9	1.487 (8)
P1—F4	1.508 (6)	C1—H1	0.9300
P1—F5	1.474 (11)	C2—H2B	0.9700
P1—F6	1.469 (11)	C2—H2A	0.9700
P1—F5ⁱ	1.474 (11)	C3—H3A	0.9700
F5—F6	1.29 (2)	C3—H3B	0.9700
O1—C5	1.372 (5)	C4—H4A	0.9700
O1—C8	1.379 (6)	C4—H4B	0.9700
N1—C2	1.459 (6)	C6—H6	0.9300
N1—C4	1.474 (5)	C7—H7	0.9300
N1—C1	1.299 (4)	C9—H9C	0.9600
C2—C3	1.491 (7)	C9—H9A	0.9600
C4—C5	1.467 (6)	C9—H9B	0.9600

F4—P1—F5ⁱ	69.5 (7)	N1—C4—C5	113.8 (3)
F4—P1—F6ⁱ	110.6 (7)	O1—C5—C6	110.2 (4)
F5—P1—F6	52.1 (9)	C4—C5—C6	133.1 (4)
F5—P1—F5ⁱ	122.0 (8)	O1—C5—C4	116.7 (4)
F5—P1—F6ⁱ	171.5 (8)	C5—C6—C7	107.4 (5)
F5ⁱ—P1—F6	171.5 (8)	C6—C7—C8	107.2 (5)
F6—P1—F6ⁱ	132.9 (9)	O1—C8—C9	115.4 (5)
F5ⁱ—P1—F6ⁱ	52.1 (9)	O1—C8—C7	109.2 (4)
F2—P1—F5ⁱ	111.4 (7)	C7—C8—C9	135.3 (6)
F2—P1—F6ⁱ	69.0 (7)	N1ⁱ—C1—H1	117.00
F3—P1—F4	94.5 (4)	N1—C1—H1	117.00
F3—P1—F5	72.2 (5)	N1—C2—H2A	110.00
F1—P1—F2	90.9 (4)	C3—C2—H2B	110.00
F1—P1—F3	178.9 (3)	N1—C2—H2B	110.00
F1—P1—F4	86.6 (4)	C3—C2—H2A	110.00
F1—P1—F5	108.3 (5)	H2A—C2—H2B	108.00
F1—P1—F6	80.2 (7)	C2ⁱ—C3—H3A	109.00
F1—P1—F5ⁱ	108.3 (5)	C2—C3—H3A	109.00
F1—P1—F6ⁱ	80.2 (7)	C2—C3—H3B	109.00
F2—P1—F3	88.0 (4)	H3A—C3—H3B	108.00
F2—P1—F4	177.5 (4)	C2ⁱ—C3—H3B	109.00
F2—P1—F5	111.4 (7)	N1—C4—H4B	109.00
F2—P1—F6	69.0 (7)	N1—C4—H4A	109.00
F4—P1—F5	69.5 (7)	H4A—C4—H4B	108.00
F4—P1—F6	110.6 (7)	C5—C4—H4A	109.00
F3—P1—F5ⁱ	72.2 (5)	C5—C4—H4B	109.00
F3—P1—F6ⁱ	99.4 (7)	C5—C6—H6	126.00
F3—P1—F6	99.4 (7)	C7—C6—H6	126.00
P1—F5—F6	63.7 (8)	C8—C7—H7	126.00
P1—F6—F5	64.2 (8)	C6—C7—H7	126.00
C5—O1—C8	105.9 (3)	H9B—C9—H9C	110.00
C1—N1—C2	120.1 (4)	C8—C9—H9A	109.00
C2—N1—C4	119.4 (4)	C8—C9—H9B	110.00
C1—N1—C4	120.5 (4)	C8—C9—H9C	109.00
N1—C1—N1ⁱ	125.9 (4)	H9A—C9—H9B	109.00
N1—C2—C3	109.6 (4)	H9A—C9—H9C	109.00
C2—C3—C2ⁱ	111.9 (6)

F5ⁱ—P1—F5—F6	−172.5 (11)	C2—N1—C1—N1ⁱ	−1.9 (7)
F1—P1—F6—F5	−122.5 (10)	C1—N1—C4—C5	−121.5 (4)
F2—P1—F6—F5	142.8 (11)	C4—N1—C1—N1ⁱ	−180.0 (4)
F1—P1—F5—F6	61.1 (11)	C2—N1—C4—C5	60.4 (5)
F2—P1—F5—F6	−37.4 (11)	C1—N1—C2—C3	−25.1 (6)
F3—P1—F5—F6	−117.9 (11)	C4—N1—C2—C3	153.1 (5)
F4—P1—F5—F6	140.1 (11)	N1—C2—C3—C2ⁱ	51.2 (7)
F3—P1—F6—F5	58.6 (10)	N1—C4—C5—C6	96.4 (6)
F4—P1—F6—F5	−39.9 (11)	N1—C4—C5—O1	−85.1 (4)
F6ⁱ—P1—F6—F5	170.8 (12)	C4—C5—C6—C7	177.5 (5)
C5—O1—C8—C7	0.9 (5)	O1—C5—C6—C7	−1.1 (6)
C5—O1—C8—C9	178.1 (4)	C5—C6—C7—C8	1.7 (6)
C8—O1—C5—C4	−178.7 (4)	C6—C7—C8—C9	−178.0 (6)
C8—O1—C5—C6	0.2 (5)	C6—C7—C8—O1	−1.6 (6)

Symmetry code: (i) x, −y+1/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···F2ⁱⁱ	0.93	2.40	3.312 (8)	167
C1—H1···F4ⁱⁱⁱ	0.93	2.52	3.044 (8)	116

Symmetry codes: (ii) x, y, z−1; (iii) x−1, y, z−1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···F2ⁱ	0.93	2.40	3.312 (8)	167
C1—H1···F4ⁱⁱ	0.93	2.52	3.044 (8)	116

Symmetry codes: (i) x, y, z−1; (ii) x−1, y, z−1.

Acknowledgements

The authors acknowledge the provision of funds for the purchase of a diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

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Volume 69| Part 8| August 2013| Page o1325

doi:10.1107/S1600536813020187

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

1,3-Bis[(5-amino­furan-2-yl)meth­yl]-3,4,5,6-tetra­hydro­pyrimidin-1-ium hexa­fluoro­phosphate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1,3-Bis[(5-aminofuran-2-yl)methyl]-3,4,5,6-tetrahydropyrimidin-1-ium hexafluorophosphate