4-(4-Pyrid-yl)pyridinium perchlorate methanol solvate.

In the cation of the title hydrated molecular salt, C(10)H(9)N(2) (+)·ClO(4) (-)·CH(3)OH, the dihedral angle formed by the pyridine rings is 28.82 (15)°. The crystal structure is stabilized by inter-molecular N-H⋯O and O-H⋯N hydrogen bonds and π-π stacking inter-actions, with centroid-to-centroid distances of 3.5913 (7) and 3.6526 (7) Å. Three O atoms of the perchlorate anion are disordered over two positions with refined occupancy factors of 0.649 (7):0.351 (7).

Related literature

For simple mol­ecular–ionic crystals containing organic cations and acid radicals, see: Katrusiak & Szafrański (1999 ▶, 2006 ▶). For the crystal structure of 4,4′-bipyridin-1-ium perchlorate di­hydrate, see: Zhang et al. (2008 ▶).

Experimental

Crystal data

C10H9N2 +·ClO4 −·CH4O

M = 288.68

Monoclinic,

a = 6.8822 (14) Å

b = 15.362 (3) Å

c = 12.254 (3) Å

β = 92.07 (3)°

V = 1294.7 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 293 K

0.3 × 0.26 × 0.2 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.62, T max = 0.81

13295 measured reflections

2956 independent reflections

1803 reflections with I > 2σ(I)

R int = 0.067

Refinement

R[F 2 > 2σ(F 2)] = 0.079

wR(F 2) = 0.210

S = 1.00

2956 reflections

201 parameters

88 restraints

H-atom parameters constrained

Δρmax = 0.63 e Å−3

Δρmin = −0.60 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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810012985/rz2430sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012985/rz2430Isup2.hkl

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

C10H9N2+·ClO4−·CH4O	F(000) = 600
Mr = 288.68	Dx = 1.481 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1803 reflections
a = 6.8822 (14) Å	θ = 3.1–27.5°
b = 15.362 (3) Å	µ = 0.31 mm−1
c = 12.254 (3) Å	T = 293 K
β = 92.07 (3)°	Block, colourless
V = 1294.7 (5) Å3	0.3 × 0.26 × 0.2 mm
Z = 4

Rigaku SCXmini diffractometer	2956 independent reflections
Radiation source: fine-focus sealed tube	1803 reflections with I > 2σ(I)
graphite	Rint = 0.067
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.1°
ω scans	h = −8→8
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −19→19
Tmin = 0.62, Tmax = 0.81	l = −15→15
13295 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)] = 0.079	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.210	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0767P)2 + 2.5927P] where P = (Fo2 + 2Fc2)/3
2956 reflections	(Δ/σ)max < 0.001
201 parameters	Δρmax = 0.63 e Å−3
88 restraints	Δρmin = −0.60 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 > 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)
C1	0.7627 (6)	0.5390 (3)	0.5916 (4)	0.0459 (11)
H1A	0.7704	0.5882	0.6356	0.055*
C2	0.7575 (6)	0.5504 (3)	0.4801 (3)	0.0395 (10)
H2A	0.7624	0.6061	0.4505	0.047*
C3	0.7449 (6)	0.4786 (3)	0.4128 (3)	0.0348 (9)
C4	0.7326 (7)	0.3979 (3)	0.4625 (4)	0.0464 (11)
H4A	0.7185	0.3478	0.4205	0.056*
C5	0.7414 (7)	0.3929 (3)	0.5742 (4)	0.0522 (12)
H5A	0.7360	0.3380	0.6060	0.063*
C6	0.6765 (7)	0.5634 (4)	0.1258 (4)	0.0564 (13)
H6A	0.6278	0.6121	0.0889	0.068*
C7	0.6747 (7)	0.5599 (3)	0.2371 (4)	0.0469 (11)
H7A	0.6270	0.6067	0.2763	0.056*
C8	0.7450 (6)	0.4859 (3)	0.2922 (3)	0.0370 (9)
C9	0.8198 (7)	0.4193 (3)	0.2298 (4)	0.0494 (11)
H9A	0.8702	0.3696	0.2637	0.059*
C10	0.8194 (8)	0.4267 (4)	0.1186 (4)	0.0565 (13)
H10A	0.8698	0.3820	0.0769	0.068*
C11	0.1539 (10)	0.6691 (3)	0.1471 (5)	0.0727 (17)
H11A	0.0837	0.6922	0.0844	0.087*
H11B	0.2789	0.6967	0.1541	0.087*
H11C	0.0823	0.6801	0.2114	0.087*
N1	0.7476 (6)	0.4972 (3)	0.0702 (3)	0.0547 (11)
H1B	0.7470	0.5003	0.0002	0.066*
N2	0.7572 (5)	0.4616 (3)	0.6398 (3)	0.0472 (9)
O5	0.1785 (5)	0.5786 (2)	0.1341 (2)	0.0537 (9)
H5	0.2107	0.5599	0.2002	0.081*
Cl1	0.32539 (19)	0.19524 (7)	0.64038 (10)	0.0531 (4)
O1	0.3132 (6)	0.1030 (2)	0.6349 (3)	0.0634 (9)
O2	0.335 (2)	0.2182 (8)	0.7540 (9)	0.0659 (15)	0.351 (7)
O3	0.1581 (17)	0.2295 (7)	0.5822 (11)	0.0606 (9)	0.351 (7)
O4	0.3801 (19)	0.2310 (7)	0.5350 (9)	0.0601 (9)	0.351 (7)
O2'	0.4433 (12)	0.2213 (4)	0.7329 (6)	0.0739 (13)	0.649 (7)
O3'	0.1388 (10)	0.2337 (4)	0.6422 (7)	0.0717 (12)	0.649 (7)
O4'	0.4702 (11)	0.2228 (4)	0.5685 (6)	0.0732 (12)	0.649 (7)

	U11	U22	U33	U12	U13	U23
C1	0.046 (3)	0.048 (3)	0.044 (3)	0.001 (2)	0.000 (2)	−0.008 (2)
C2	0.042 (2)	0.036 (2)	0.040 (2)	0.0015 (18)	−0.0002 (18)	0.0001 (17)
C3	0.032 (2)	0.039 (2)	0.034 (2)	0.0004 (17)	0.0020 (16)	0.0025 (17)
C4	0.062 (3)	0.036 (2)	0.041 (2)	−0.005 (2)	−0.001 (2)	−0.0002 (18)
C5	0.065 (3)	0.049 (3)	0.042 (2)	−0.004 (2)	0.003 (2)	0.009 (2)
C6	0.050 (3)	0.073 (3)	0.046 (3)	−0.002 (3)	−0.001 (2)	0.018 (3)
C7	0.049 (3)	0.050 (3)	0.042 (2)	0.003 (2)	0.004 (2)	0.008 (2)
C8	0.034 (2)	0.043 (2)	0.033 (2)	−0.0030 (18)	0.0007 (17)	0.0013 (17)
C9	0.055 (3)	0.051 (3)	0.042 (3)	0.005 (2)	0.003 (2)	−0.005 (2)
C10	0.059 (3)	0.073 (4)	0.038 (3)	−0.002 (3)	0.002 (2)	−0.011 (2)
C11	0.110 (5)	0.051 (3)	0.056 (3)	0.008 (3)	−0.010 (3)	−0.003 (3)
N1	0.043 (2)	0.089 (3)	0.0322 (19)	−0.011 (2)	−0.0008 (17)	0.004 (2)
N2	0.047 (2)	0.059 (2)	0.0356 (19)	−0.0010 (18)	0.0017 (16)	0.0006 (18)
O5	0.082 (2)	0.0453 (18)	0.0341 (16)	0.0012 (16)	−0.0031 (15)	0.0001 (13)
Cl1	0.0674 (8)	0.0371 (6)	0.0546 (7)	−0.0098 (5)	0.0003 (5)	−0.0051 (5)
O1	0.093 (2)	0.0369 (12)	0.0603 (19)	−0.0094 (12)	0.0059 (17)	−0.0059 (12)
O2	0.084 (3)	0.055 (3)	0.0592 (16)	−0.012 (3)	0.000 (2)	−0.015 (2)
O3	0.0715 (16)	0.0479 (16)	0.0622 (17)	−0.0064 (14)	−0.0005 (14)	−0.0015 (16)
O4	0.0722 (17)	0.0470 (16)	0.0609 (15)	−0.0095 (16)	0.0001 (15)	0.0018 (14)
O2'	0.084 (3)	0.063 (2)	0.074 (2)	−0.014 (3)	−0.010 (2)	−0.019 (2)
O3'	0.0757 (18)	0.062 (2)	0.077 (3)	0.0039 (18)	0.004 (2)	−0.011 (2)
O4'	0.074 (2)	0.066 (2)	0.080 (2)	−0.017 (2)	0.007 (2)	0.012 (2)

C1—N2	1.329 (6)	C9—H9A	0.9300
C1—C2	1.376 (6)	C10—N1	1.322 (7)
C1—H1A	0.9300	C10—H10A	0.9300
C2—C3	1.379 (6)	C11—O5	1.411 (6)
C2—H2A	0.9300	C11—H11A	0.9600
C3—C4	1.384 (6)	C11—H11B	0.9600
C3—C8	1.481 (5)	C11—H11C	0.9600
C4—C5	1.370 (6)	N1—H1B	0.8600
C4—H4A	0.9300	O5—H5	0.8804
C5—N2	1.329 (6)	Cl1—O3'	1.415 (7)
C5—H5A	0.9300	Cl1—O4'	1.419 (6)
C6—N1	1.327 (7)	Cl1—O1	1.420 (3)
C6—C7	1.366 (7)	Cl1—O2'	1.428 (6)
C6—H6A	0.9300	Cl1—O3	1.432 (12)
C7—C8	1.400 (6)	Cl1—O2	1.435 (11)
C7—H7A	0.9300	Cl1—O4	1.465 (11)
C8—C9	1.387 (6)	O3—O4	1.653 (19)
C9—C10	1.368 (6)
N2—C1—C2	123.8 (4)	O5—C11—H11B	109.5
N2—C1—H1A	118.1	H11A—C11—H11B	109.5
C2—C1—H1A	118.1	O5—C11—H11C	109.5
C1—C2—C3	119.3 (4)	H11A—C11—H11C	109.5
C1—C2—H2A	120.3	H11B—C11—H11C	109.5
C3—C2—H2A	120.3	C10—N1—C6	122.5 (4)
C2—C3—C4	117.2 (4)	C10—N1—H1B	118.8
C2—C3—C8	122.3 (4)	C6—N1—H1B	118.8
C4—C3—C8	120.6 (4)	C1—N2—C5	116.4 (4)
C5—C4—C3	119.3 (4)	C11—O5—H5	104.2
C5—C4—H4A	120.4	O3'—Cl1—O4'	122.9 (5)
C3—C4—H4A	120.4	O3'—Cl1—O1	111.4 (3)
N2—C5—C4	124.0 (4)	O4'—Cl1—O1	108.1 (3)
N2—C5—H5A	118.0	O3'—Cl1—O2'	111.1 (4)
C4—C5—H5A	118.0	O4'—Cl1—O2'	91.0 (6)
N1—C6—C7	120.0 (5)	O1—Cl1—O2'	110.4 (3)
N1—C6—H6A	120.0	O4'—Cl1—O3	98.7 (7)
C7—C6—H6A	120.0	O1—Cl1—O3	107.3 (5)
C6—C7—C8	119.9 (5)	O2'—Cl1—O3	135.7 (6)
C6—C7—H7A	120.1	O3'—Cl1—O2	83.7 (6)
C8—C7—H7A	120.1	O4'—Cl1—O2	121.4 (7)
C9—C8—C7	117.5 (4)	O1—Cl1—O2	106.9 (5)
C9—C8—C3	120.5 (4)	O3—Cl1—O2	113.5 (7)
C7—C8—C3	122.0 (4)	O3'—Cl1—O4	96.9 (7)
C10—C9—C8	120.0 (5)	O1—Cl1—O4	110.4 (5)
C10—C9—H9A	120.0	O2'—Cl1—O4	116.0 (7)
C8—C9—H9A	120.0	O3—Cl1—O4	69.6 (8)
N1—C10—C9	120.1 (5)	O2—Cl1—O4	139.4 (7)
N1—C10—H10A	119.9	Cl1—O3—O4	56.1 (6)
C9—C10—H10A	119.9	Cl1—O4—O3	54.3 (6)
O5—C11—H11A	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···N2i	0.88	1.99	2.857 (5)	167
N1—H1B···O5ii	0.86	2.12	2.825 (5)	139
N1—H1B···O1iii	0.86	2.31	3.010 (5)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯N2i	0.88	1.99	2.857 (5)	167
N1—H1B⋯O5ii	0.86	2.12	2.825 (5)	139
N1—H1B⋯O1iii	0.86	2.31	3.010 (5)	138

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