4-Carbamoylpyridinium perchlorate.

In the cation of the title compound, C(6)H(7)N(2)O(+)·ClO(4) (-), the amide group is oriented at a dihedral angle of 10.41 (17)° to the benzene ring. The crystal structure is stabilized by inter-molecular N-H⋯O hydrogen bonding.

Related literature

For general background to structural features and physical properties of simple mol­ecular–ionic crystals containing organic cations and acid radicals (1:1 molar ratio), see: Czupiński et al. (2002 ▶); Katrusiak & Szafrański (1999 ▶, 2006 ▶). For the crystal structure of 4-carbamoylpyridinium dihydrogen phosphate, see: Gholivand et al. (2007 ▶) and for that of 3-(amino­carbon­yl)pyridinium perchlorate, see: Athimoolam & Natarajan (2007 ▶).

Experimental

Crystal data

C6H7N2O+·ClO4 −

M = 222.59

Monoclinic,

a = 10.935 (2) Å

b = 10.082 (2) Å

c = 8.2021 (16) Å

β = 99.37 (3)°

V = 892.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.43 mm−1

T = 293 K

0.30 × 0.25 × 0.22 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.87, T max = 0.90

8863 measured reflections

2033 independent reflections

1421 reflections with I > 2σ(I)

R int = 0.074

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.176

S = 1.04

2033 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.42 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: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809039026/xu2591sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039026/xu2591Isup2.hkl

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

C6H7N2O+·ClO4−	F(000) = 456
Mr = 222.59	Dx = 1.657 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1421 reflections
a = 10.935 (2) Å	θ = 3.2–27.5°
b = 10.082 (2) Å	µ = 0.43 mm−1
c = 8.2021 (16) Å	T = 293 K
β = 99.37 (3)°	Block, colorless
V = 892.2 (3) Å3	0.30 × 0.25 × 0.22 mm
Z = 4

Rigaku SCXmini diffractometer	2033 independent reflections
Radiation source: fine-focus sealed tube	1421 reflections with I > 2σ(I)
graphite	Rint = 0.074
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.2°
ω scans	h = −14→14
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −13→13
Tmin = 0.87, Tmax = 0.90	l = −10→10
8863 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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.176	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0844P)2 + 0.3072P] where P = (Fo2 + 2Fc2)/3
2033 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.42 e Å−3

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
Cl1	0.35049 (7)	0.39747 (7)	0.09900 (9)	0.0473 (3)
O5	0.0368 (2)	0.8048 (2)	0.2309 (3)	0.0650 (7)
N2	−0.0251 (3)	0.5945 (3)	0.1873 (4)	0.0698 (10)
H2A	−0.0862	0.6169	0.1127	0.084*
H2B	−0.0128	0.5123	0.2130	0.084*
C6	0.0493 (3)	0.6856 (3)	0.2619 (4)	0.0463 (7)
C4	0.2469 (3)	0.7332 (3)	0.4470 (4)	0.0479 (8)
H4A	0.2386	0.8205	0.4104	0.057*
N1	0.3573 (2)	0.5717 (3)	0.6122 (3)	0.0541 (8)
H1A	0.4218	0.5492	0.6813	0.065*
C3	0.1569 (2)	0.6406 (3)	0.3883 (3)	0.0399 (7)
O4	0.4364 (2)	0.2906 (2)	0.1204 (3)	0.0707 (8)
O3	0.3944 (2)	0.4992 (2)	0.2176 (3)	0.0653 (7)
C2	0.1692 (3)	0.5117 (3)	0.4485 (4)	0.0457 (8)
H2C	0.1096	0.4479	0.4117	0.055*
C5	0.3479 (3)	0.6961 (4)	0.5590 (4)	0.0549 (9)
H5A	0.4094	0.7575	0.5973	0.066*
O2	0.3407 (3)	0.4505 (3)	−0.0636 (3)	0.0843 (9)
O1	0.2315 (2)	0.3517 (3)	0.1231 (4)	0.0759 (8)
C1	0.2713 (3)	0.4798 (3)	0.5636 (4)	0.0536 (9)
H1B	0.2803	0.3945	0.6072	0.064*

	U11	U22	U33	U12	U13	U23
Cl1	0.0405 (5)	0.0430 (5)	0.0519 (5)	0.0012 (3)	−0.0116 (3)	0.0000 (3)
O5	0.0581 (15)	0.0403 (14)	0.0867 (19)	0.0094 (11)	−0.0176 (12)	0.0095 (12)
N2	0.0575 (19)	0.0488 (18)	0.087 (2)	−0.0020 (13)	−0.0377 (17)	0.0116 (15)
C6	0.0397 (17)	0.0405 (18)	0.0548 (19)	0.0032 (13)	−0.0039 (13)	0.0050 (14)
C4	0.0466 (18)	0.0361 (16)	0.057 (2)	−0.0056 (13)	−0.0036 (14)	0.0033 (13)
N1	0.0460 (16)	0.0565 (18)	0.0509 (17)	0.0061 (12)	−0.0187 (13)	−0.0010 (12)
C3	0.0346 (16)	0.0371 (15)	0.0448 (17)	0.0021 (11)	−0.0030 (12)	−0.0012 (12)
O4	0.0550 (15)	0.0510 (15)	0.097 (2)	0.0147 (11)	−0.0145 (14)	−0.0040 (13)
O3	0.0595 (16)	0.0570 (15)	0.0721 (17)	−0.0015 (11)	−0.0110 (12)	−0.0208 (12)
C2	0.0469 (18)	0.0319 (15)	0.0520 (19)	−0.0018 (12)	−0.0109 (14)	−0.0034 (12)
C5	0.0438 (19)	0.055 (2)	0.060 (2)	−0.0120 (15)	−0.0079 (15)	−0.0007 (16)
O2	0.106 (2)	0.087 (2)	0.0518 (17)	−0.0028 (17)	−0.0107 (15)	0.0126 (14)
O1	0.0434 (15)	0.0839 (19)	0.096 (2)	−0.0120 (13)	−0.0021 (13)	−0.0088 (16)
C1	0.060 (2)	0.0381 (17)	0.055 (2)	0.0063 (15)	−0.0145 (16)	−0.0002 (14)

Cl1—O4	1.421 (2)	C4—C3	1.385 (4)
Cl1—O2	1.424 (3)	C4—H4A	0.9300
Cl1—O1	1.425 (3)	N1—C5	1.327 (4)
Cl1—O3	1.441 (2)	N1—C1	1.334 (4)
O5—C6	1.231 (3)	N1—H1A	0.8600
N2—C6	1.310 (4)	C3—C2	1.389 (4)
N2—H2A	0.8600	C2—C1	1.377 (4)
N2—H2B	0.8600	C2—H2C	0.9300
C6—C3	1.507 (4)	C5—H5A	0.9300
C4—C5	1.369 (5)	C1—H1B	0.9300
O4—Cl1—O2	110.33 (19)	C5—N1—C1	123.0 (3)
O4—Cl1—O1	109.76 (17)	C5—N1—H1A	118.5
O2—Cl1—O1	108.68 (18)	C1—N1—H1A	118.5
O4—Cl1—O3	108.36 (15)	C4—C3—C2	119.0 (3)
O2—Cl1—O3	109.30 (18)	C4—C3—C6	117.9 (3)
O1—Cl1—O3	110.41 (17)	C2—C3—C6	123.1 (3)
C6—N2—H2A	120.0	C1—C2—C3	118.9 (3)
C6—N2—H2B	120.0	C1—C2—H2C	120.6
H2A—N2—H2B	120.0	C3—C2—H2C	120.6
O5—C6—N2	123.2 (3)	N1—C5—C4	119.3 (3)
O5—C6—C3	118.9 (3)	N1—C5—H5A	120.3
N2—C6—C3	117.8 (3)	C4—C5—H5A	120.3
C5—C4—C3	120.0 (3)	N1—C1—C2	119.7 (3)
C5—C4—H4A	120.0	N1—C1—H1B	120.1
C3—C4—H4A	120.0	C2—C1—H1B	120.1
C5—C4—C3—C2	1.9 (5)	C4—C3—C2—C1	−0.6 (5)
C5—C4—C3—C6	−178.4 (3)	C6—C3—C2—C1	179.7 (3)
O5—C6—C3—C4	−9.0 (5)	C1—N1—C5—C4	−1.0 (5)
N2—C6—C3—C4	169.5 (3)	C3—C4—C5—N1	−1.2 (5)
O5—C6—C3—C2	170.7 (3)	C5—N1—C1—C2	2.4 (5)
N2—C6—C3—C2	−10.9 (5)	C3—C2—C1—N1	−1.5 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3i	0.86	2.10	2.932 (4)	162
N2—H2A···O1ii	0.86	2.32	3.162 (4)	168
N2—H2B···O5iii	0.86	2.17	3.004 (4)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O3i	0.86	2.10	2.932 (4)	162
N2—H2A⋯O1ii	0.86	2.32	3.162 (4)	168
N2—H2B⋯O5iii	0.86	2.17	3.004 (4)	164

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