4-(N-Propan-2-ylcarbamo-yl)pyridinium perchlorate.

In the title compound, C(9)H(13)N(2)O(+)·ClO(4) (-), the dihedral angle between the planes of the amide group and the pyridinium fragment is 34.11 (14)°. In the crystal, the cations are connected by N-H⋯O hydrogen bonds between the amide groups into chains extended along the a axis. Hydrogen bonds between the pyridinium N-H group and the perchlorate anions organize the chains into a two-dimensional network.

Related literature

For the physical properties of simple mol­ecular–ionic crystals, see: Czupiński et al., 2002 ▶; Katrusiak & Szafrański (1999 ▶, 2006 ▶). For related structures, see: Gholivand et al. (2007 ▶); Chen (2009 ▶); Zhang et al. (2009 ▶).

Experimental

Crystal data

C9H13N2O+·ClO4 −

M = 264.66

Triclinic,

a = 4.9342 (3) Å

b = 8.973 (4) Å

c = 13.715 (10) Å

α = 93.046 (12)°

β = 91.07 (2)°

γ = 101.01 (3)°

V = 594.9 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.33 mm−1

T = 298 K

0.2 × 0.2 × 0.2 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.887, T max = 1.000

6065 measured reflections

2708 independent reflections

2160 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.159

S = 1.07

2708 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.78 e Å−3

Δρmin = −0.58 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: PRPKAPPA (Ferguson, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810019306/gk2274sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810019306/gk2274Isup2.hkl

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

C9H13N2O+·ClO4−	Z = 2
Mr = 264.66	F(000) = 276
Triclinic, P1	Dx = 1.477 Mg m−3
Hall symbol: -P 1	Melting point: 408 K
a = 4.9342 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.973 (4) Å	Cell parameters from 1631 reflections
c = 13.715 (10) Å	θ = 2.3–27.4°
α = 93.046 (12)°	µ = 0.33 mm−1
β = 91.07 (2)°	T = 298 K
γ = 101.01 (3)°	Prism, colourless
V = 594.9 (5) Å3	0.2 × 0.2 × 0.2 mm

Rigaku SCXmini diffractometer	2708 independent reflections
Radiation source: fine-focus sealed tube	2160 reflections with I > 2σ(I)
graphite	Rint = 0.024
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 2.3°
ω scans	h = −6→6
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −11→11
Tmin = 0.887, Tmax = 1.000	l = −17→17
6065 measured reflections

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.078P)2 + 0.3515P] where P = (Fo2 + 2Fc2)/3
2708 reflections	(Δ/σ)max = 0.001
154 parameters	Δρmax = 0.78 e Å−3
0 restraints	Δρmin = −0.58 e Å−3

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. 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 > 2sigma(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
C1	0.8695 (6)	0.8140 (3)	0.8363 (2)	0.0502 (7)
H1A	0.8291	0.9111	0.8408	0.060*
C2	0.7491 (5)	0.7102 (3)	0.76352 (19)	0.0428 (6)
H2A	0.6249	0.7363	0.7187	0.051*
C3	0.8135 (4)	0.5660 (2)	0.75713 (17)	0.0329 (5)
C4	0.9972 (5)	0.5295 (3)	0.82555 (19)	0.0398 (5)
H4A	1.0437	0.4337	0.8223	0.048*
C5	1.1098 (5)	0.6358 (3)	0.8980 (2)	0.0463 (6)
H5A	1.2303	0.6120	0.9451	0.056*
C6	0.6751 (5)	0.4515 (3)	0.67827 (17)	0.0340 (5)
C7	0.7297 (5)	0.2295 (3)	0.5718 (2)	0.0452 (6)
H7A	0.5280	0.2151	0.5658	0.054*
C8	0.8048 (8)	0.0860 (3)	0.6075 (2)	0.0616 (8)
H8A	0.7233	0.0652	0.6695	0.092*
H8B	1.0020	0.0989	0.6144	0.092*
H8C	0.7368	0.0026	0.5612	0.092*
C9	0.8498 (9)	0.2688 (4)	0.4730 (2)	0.0703 (10)
H9A	0.7961	0.3603	0.4532	0.105*
H9B	0.7815	0.1871	0.4256	0.105*
H9C	1.0476	0.2840	0.4779	0.105*
Cl1	0.42620 (12)	0.18228 (8)	0.88680 (5)	0.0452 (2)
N1	1.0451 (5)	0.7740 (3)	0.90049 (17)	0.0485 (6)
H1B	1.1202	0.8401	0.9455	0.058*
N2	0.8294 (4)	0.3550 (2)	0.64449 (17)	0.0436 (5)
H2B	0.9970	0.3667	0.6664	0.052*
O1	0.4371 (3)	0.4521 (2)	0.65134 (14)	0.0471 (5)
O2	0.7111 (4)	0.1708 (2)	0.89323 (17)	0.0577 (5)
O3	0.3117 (6)	0.1454 (5)	0.79332 (19)	0.1241 (15)
O4	0.4067 (6)	0.3375 (3)	0.9161 (3)	0.0938 (10)
O5	0.2732 (4)	0.0877 (2)	0.95541 (15)	0.0526 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0574 (17)	0.0369 (13)	0.0581 (17)	0.0166 (12)	−0.0001 (13)	−0.0063 (12)
C2	0.0470 (14)	0.0389 (13)	0.0455 (14)	0.0165 (11)	−0.0033 (11)	0.0007 (10)
C3	0.0292 (10)	0.0301 (11)	0.0395 (12)	0.0063 (8)	0.0031 (9)	0.0008 (9)
C4	0.0389 (12)	0.0359 (12)	0.0459 (13)	0.0116 (10)	−0.0041 (10)	−0.0010 (10)
C5	0.0434 (14)	0.0511 (15)	0.0447 (14)	0.0123 (12)	−0.0060 (11)	−0.0022 (12)
C6	0.0290 (10)	0.0332 (11)	0.0394 (12)	0.0055 (9)	−0.0014 (9)	0.0010 (9)
C7	0.0358 (12)	0.0429 (14)	0.0553 (16)	0.0094 (10)	−0.0100 (11)	−0.0155 (12)
C8	0.085 (2)	0.0424 (15)	0.0561 (18)	0.0112 (15)	0.0005 (16)	−0.0060 (13)
C9	0.101 (3)	0.0553 (18)	0.0536 (18)	0.0164 (18)	−0.0149 (17)	−0.0046 (14)
Cl1	0.0334 (3)	0.0543 (4)	0.0474 (4)	0.0041 (3)	−0.0046 (2)	0.0162 (3)
N1	0.0520 (13)	0.0465 (13)	0.0451 (12)	0.0094 (10)	−0.0022 (10)	−0.0141 (10)
N2	0.0279 (10)	0.0429 (11)	0.0583 (13)	0.0093 (8)	−0.0097 (9)	−0.0169 (10)
O1	0.0309 (9)	0.0515 (11)	0.0599 (12)	0.0135 (8)	−0.0094 (8)	−0.0047 (9)
O2	0.0352 (10)	0.0632 (13)	0.0764 (14)	0.0129 (9)	0.0019 (9)	0.0071 (10)
O3	0.0714 (18)	0.243 (4)	0.0419 (14)	−0.011 (2)	−0.0133 (12)	0.0139 (19)
O4	0.0700 (16)	0.0436 (12)	0.174 (3)	0.0203 (11)	−0.0057 (17)	0.0286 (15)
O5	0.0568 (12)	0.0467 (11)	0.0558 (12)	0.0098 (9)	0.0161 (9)	0.0115 (9)

C1—N1	1.333 (4)	C7—C9	1.521 (5)
C1—C2	1.373 (4)	C7—H7A	0.9800
C1—H1A	0.9300	C8—H8A	0.9600
C2—C3	1.388 (3)	C8—H8B	0.9600
C2—H2A	0.9300	C8—H8C	0.9600
C3—C4	1.387 (3)	C9—H9A	0.9600
C3—C6	1.509 (3)	C9—H9B	0.9600
C4—C5	1.372 (4)	C9—H9C	0.9600
C4—H4A	0.9300	Cl1—O3	1.389 (3)
C5—N1	1.337 (3)	Cl1—O5	1.429 (2)
C5—H5A	0.9300	Cl1—O2	1.4305 (19)
C6—O1	1.226 (3)	Cl1—O4	1.450 (3)
C6—N2	1.329 (3)	N1—H1B	0.8600
C7—N2	1.468 (3)	N2—H2B	0.8600
C7—C8	1.509 (4)
N1—C1—C2	119.3 (2)	C7—C8—H8A	109.5
N1—C1—H1A	120.3	C7—C8—H8B	109.5
C2—C1—H1A	120.3	H8A—C8—H8B	109.5
C1—C2—C3	119.7 (2)	C7—C8—H8C	109.5
C1—C2—H2A	120.1	H8A—C8—H8C	109.5
C3—C2—H2A	120.1	H8B—C8—H8C	109.5
C4—C3—C2	119.0 (2)	C7—C9—H9A	109.5
C4—C3—C6	121.7 (2)	C7—C9—H9B	109.5
C2—C3—C6	119.3 (2)	H9A—C9—H9B	109.5
C5—C4—C3	119.5 (2)	C7—C9—H9C	109.5
C5—C4—H4A	120.3	H9A—C9—H9C	109.5
C3—C4—H4A	120.3	H9B—C9—H9C	109.5
N1—C5—C4	119.5 (2)	O3—Cl1—O5	110.28 (18)
N1—C5—H5A	120.2	O3—Cl1—O2	112.70 (17)
C4—C5—H5A	120.2	O5—Cl1—O2	109.78 (13)
O1—C6—N2	125.5 (2)	O3—Cl1—O4	109.5 (2)
O1—C6—C3	119.7 (2)	O5—Cl1—O4	106.56 (16)
N2—C6—C3	114.83 (19)	O2—Cl1—O4	107.79 (14)
N2—C7—C8	108.7 (2)	C1—N1—C5	123.0 (2)
N2—C7—C9	109.9 (2)	C1—N1—H1B	118.5
C8—C7—C9	112.4 (2)	C5—N1—H1B	118.5
N2—C7—H7A	108.6	C6—N2—C7	123.7 (2)
C8—C7—H7A	108.6	C6—N2—H2B	118.2
C9—C7—H7A	108.6	C7—N2—H2B	118.2
N1—C1—C2—C3	−0.6 (4)	C4—C3—C6—N2	−34.6 (3)
C1—C2—C3—C4	0.7 (4)	C2—C3—C6—N2	147.5 (2)
C1—C2—C3—C6	178.6 (2)	C2—C1—N1—C5	−0.4 (4)
C2—C3—C4—C5	0.3 (4)	C4—C5—N1—C1	1.4 (4)
C6—C3—C4—C5	−177.6 (2)	O1—C6—N2—C7	−2.7 (4)
C3—C4—C5—N1	−1.3 (4)	C3—C6—N2—C7	176.5 (2)
C4—C3—C6—O1	144.7 (2)	C8—C7—N2—C6	−131.6 (3)
C2—C3—C6—O1	−33.2 (3)	C9—C7—N2—C6	105.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O5i	0.86	2.20	2.879 (3)	136
N1—H1B···O2ii	0.86	2.36	3.032 (4)	135
N1—H1B···O5iii	0.86	2.55	2.918 (3)	107
N2—H2B···O1iv	0.86	2.18	2.957 (3)	150
C1—H1A···O2v	0.93	2.58	3.491 (4)	168
C4—H4A···O4iv	0.93	2.50	3.171 (3)	130
C5—H5A···O4ii	0.93	2.55	3.426 (4)	157
C7—H7A···O1	0.98	2.49	2.863 (3)	102

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O5i	0.86	2.20	2.879 (3)	136
N1—H1B⋯O2ii	0.86	2.36	3.032 (4)	135
N2—H2B⋯O1iii	0.86	2.18	2.957 (3)	150

Symmetry codes: (i) ; (ii) ; (iii) .