2-{5-[N-(2-Pyridyl)carbamo-yl]pentan-amido}pyridinium hexa-fluoro-phosphate.

In the crystal structure of the title compound, C(16)H(19)N(4)O(2) (+)·PF(6) (-), the cations and anions are situated on centres of inversion. Thus, the N-H H atom is disordered over both N atoms due to symmetry. In the crystal, mol-ecules are connected via N-H⋯F and N-H⋯O hydrogen bonds. The cation adopts the ⋯AAA⋯ trans conformation in the solid state.

Related literature

For similar structures, see: Chen et al. (2007 ▶).

Experimental

Crystal data

C16H19N4O2 +·n class="Gene">PF6 −

M = 444.32

Monoclinic,

a = 6.2119 (18) Å

b = 12.9265 (11) Å

c = 11.439 (2) Å

β = 96.415 (10)°

V = 912.8 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 295 K

0.5 × 0.2 × 0.2 mm

Data collection

Bruker P4 diffractometer

Absorption correction: multi-scan (XSCANS; Siemens, 1995 ▶) T min = 0.945, T max = 0.962

2288 measured reflections

1612 independent reflections

1334 reflections with I > 2σ(I)

R int = 0.020

3 standard reflections every 97 reflections intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.096

S = 1.07

1612 reflections

133 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.30 e Å−3

Data collection: XSCANS (Siemens, 1995 ▶); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809026488/nc2150sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809026488/nc2150Isup2.hkl

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

C16H19N4O2+·PF6−	F(000) = 456
Mr = 444.32	Dx = 1.617 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 27 reflections
a = 6.2119 (18) Å	θ = 5.1–12.5°
b = 12.9265 (11) Å	µ = 0.23 mm−1
c = 11.439 (2) Å	T = 295 K
β = 96.415 (10)°	Plate, colorless
V = 912.8 (3) Å3	0.5 × 0.2 × 0.2 mm
Z = 2

Bruker P4 diffractometer	1334 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
graphite	θmax = 25.0°, θmin = 2.4°
ω scans	h = −1→7
Absorption correction: multi-scan (XSCANS; Siemens, 1995)	k = −15→1
Tmin = 0.945, Tmax = 0.962	l = −13→13
2288 measured reflections	3 standard reflections every 97 reflections
1612 independent reflections	intensity decay: none

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0403P)2 + 0.4314P] where P = (Fo2 + 2Fc2)/3
1612 reflections	(Δ/σ)max < 0.001
133 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

Experimental. 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.

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
P	0.0000	0.5000	0.0000	0.0275 (2)
F1	0.0589 (2)	0.37673 (9)	−0.03443 (10)	0.0367 (3)
F2	0.2624 (2)	0.52790 (12)	0.01505 (15)	0.0549 (4)
F3	−0.0162 (3)	0.53230 (11)	−0.14390 (11)	0.0517 (4)
O	−0.0438 (3)	0.16414 (14)	0.01248 (14)	0.0526 (5)
N1	0.2814 (3)	0.26186 (14)	0.14024 (15)	0.0331 (4)
H1A	0.1777	0.2752	0.0861	0.040*	0.50
N2	0.0760 (3)	0.12150 (15)	0.20013 (15)	0.0352 (4)
H2A	0.0473	0.0858	0.2599	0.042*
C1	0.4629 (4)	0.32123 (18)	0.1488 (2)	0.0387 (5)
H1B	0.4739	0.3749	0.0957	0.046*
C2	0.6283 (4)	0.30293 (19)	0.2341 (2)	0.0410 (5)
H2B	0.7533	0.3430	0.2392	0.049*
C3	0.6078 (4)	0.22297 (19)	0.3140 (2)	0.0386 (5)
H3A	0.7187	0.2102	0.3739	0.046*
C4	0.4248 (4)	0.16336 (18)	0.30451 (18)	0.0347 (5)
H4A	0.4107	0.1102	0.3579	0.042*
C5	0.2600 (3)	0.18256 (16)	0.21465 (17)	0.0300 (5)
C6	−0.0652 (4)	0.11249 (17)	0.09912 (19)	0.0336 (5)
C7	−0.2390 (4)	0.03259 (18)	0.10327 (19)	0.0365 (5)
H7A	−0.3056	0.0409	0.1755	0.044*
H7B	−0.1743	−0.0357	0.1041	0.044*
C8	−0.4124 (4)	0.04088 (18)	−0.0011 (2)	0.0375 (5)
H8A	−0.4784	0.1089	−0.0012	0.045*
H8B	−0.3451	0.0339	−0.0733	0.045*

	U11	U22	U33	U12	U13	U23
P	0.0269 (4)	0.0280 (4)	0.0265 (4)	−0.0007 (3)	−0.0013 (3)	−0.0024 (3)
F1	0.0443 (7)	0.0275 (6)	0.0364 (6)	0.0055 (6)	−0.0032 (5)	−0.0043 (5)
F2	0.0268 (7)	0.0474 (8)	0.0887 (12)	−0.0045 (6)	−0.0011 (7)	−0.0043 (8)
F3	0.0854 (11)	0.0420 (8)	0.0276 (7)	0.0119 (7)	0.0052 (7)	0.0018 (6)
O	0.0577 (12)	0.0553 (11)	0.0398 (9)	−0.0212 (9)	−0.0163 (8)	0.0162 (8)
N1	0.0326 (10)	0.0340 (10)	0.0319 (9)	−0.0024 (8)	−0.0009 (8)	0.0032 (8)
N2	0.0315 (10)	0.0448 (11)	0.0282 (9)	−0.0073 (9)	−0.0020 (7)	0.0074 (8)
C1	0.0428 (13)	0.0332 (12)	0.0395 (12)	−0.0057 (10)	0.0023 (10)	0.0022 (10)
C2	0.0328 (12)	0.0410 (13)	0.0482 (13)	−0.0077 (10)	−0.0002 (10)	−0.0053 (11)
C3	0.0307 (11)	0.0445 (14)	0.0381 (12)	0.0037 (10)	−0.0077 (9)	−0.0038 (10)
C4	0.0333 (12)	0.0385 (12)	0.0305 (10)	0.0014 (10)	−0.0040 (9)	0.0043 (9)
C5	0.0277 (11)	0.0336 (11)	0.0281 (10)	0.0009 (9)	0.0007 (8)	0.0005 (9)
C6	0.0325 (11)	0.0342 (11)	0.0329 (11)	0.0008 (9)	−0.0022 (9)	0.0012 (9)
C7	0.0367 (12)	0.0382 (12)	0.0330 (11)	−0.0049 (10)	−0.0023 (9)	0.0004 (10)
C8	0.0353 (11)	0.0362 (12)	0.0394 (12)	−0.0046 (10)	−0.0024 (10)	0.0009 (10)

P—F2i	1.6596 (14)	C1—H1B	0.9300
P—F2	1.6596 (14)	C2—C3	1.395 (3)
P—F3	1.6902 (13)	C2—H2B	0.9300
P—F3i	1.6902 (13)	C3—C4	1.368 (3)
P—F1	1.6912 (12)	C3—H3A	0.9300
P—F1i	1.6913 (12)	C4—C5	1.389 (3)
O—C6	1.214 (3)	C4—H4A	0.9300
N1—C5	1.348 (3)	C6—C7	1.499 (3)
N1—C1	1.358 (3)	C7—C8	1.520 (3)
N1—H1A	0.8600	C7—H7A	0.9700
N2—C6	1.375 (3)	C7—H7B	0.9700
N2—C5	1.383 (3)	C8—C8ii	1.519 (4)
N2—H2A	0.8600	C8—H8A	0.9700
C1—C2	1.356 (3)	C8—H8B	0.9700
F2i—P—F2	180.0	C3—C2—H2B	120.5
F2i—P—F3	90.09 (8)	C4—C3—C2	120.1 (2)
F2—P—F3	89.91 (8)	C4—C3—H3A	120.0
F2i—P—F3i	89.91 (8)	C2—C3—H3A	120.0
F2—P—F3i	90.09 (8)	C3—C4—C5	119.7 (2)
F3—P—F3i	180.00 (9)	C3—C4—H4A	120.2
F2i—P—F1	90.39 (7)	C5—C4—H4A	120.2
F2—P—F1	89.61 (7)	N1—C5—N2	119.76 (18)
F3—P—F1	89.82 (6)	N1—C5—C4	119.09 (19)
F3i—P—F1	90.18 (6)	N2—C5—C4	121.14 (19)
F2i—P—F1i	89.61 (7)	O—C6—N2	121.4 (2)
F2—P—F1i	90.39 (7)	O—C6—C7	123.3 (2)
F3—P—F1i	90.18 (6)	N2—C6—C7	115.21 (18)
F3i—P—F1i	89.82 (6)	C6—C7—C8	112.12 (18)
F1—P—F1i	180.00 (8)	C6—C7—H7A	109.2
C5—N1—C1	121.58 (19)	C8—C7—H7A	109.2
C5—N1—H1A	119.2	C6—C7—H7B	109.2
C1—N1—H1A	119.2	C8—C7—H7B	109.2
C6—N2—C5	126.15 (18)	H7A—C7—H7B	107.9
C6—N2—H2A	116.9	C8ii—C8—C7	112.6 (2)
C5—N2—H2A	116.9	C8ii—C8—H8A	109.1
C2—C1—N1	120.6 (2)	C7—C8—H8A	109.1
C2—C1—H1B	119.7	C8ii—C8—H8B	109.1
N1—C1—H1B	119.7	C7—C8—H8B	109.1
C1—C2—C3	118.9 (2)	H8A—C8—H8B	107.8
C1—C2—H2B	120.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···F1	0.86	1.98	2.737 (2)	145
N1—H1A···O	0.86	2.10	2.674 (2)	124
N2—H2A···F3iii	0.86	1.95	2.774 (2)	161
N2—H2A···F1iii	0.86	2.40	3.050 (2)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯F1	0.86	1.98	2.737 (2)	145
N1—H1A⋯O	0.86	2.10	2.674 (2)	124
N2—H2A⋯F3i	0.86	1.95	2.774 (2)	161
N2—H2A⋯F1i	0.86	2.40	3.050 (2)	133

Symmetry code: (i) .