3,3'-Carbonyl-dipyridinium bis-(perchlorate).

In the title molecular salt, C(11)H(10)N(2)O(2+)·2ClO(4) (-), the complete cation is generated by crystallographic twofold symmetry. The dihedral angle between the pyridyl rings is 67.07 (7)°. The crystal structure features N-H⋯Cl hydrogen bonds, forming sheets in the ab plane.

Related literature

For the dipyridyl ketone dication, see: Crook & McElvain (1930 ▶); Favaro et al. (1990 ▶). For metal complexes of di-3-pyridyl ketone, see: Chen & Mak (2005 ▶); Chen et al. (2009 ▶).

Experimental

Crystal data

C11H10N2O2+·2ClO4 −

M = 385.11

Orthorhombic,

a = 8.5315 (3) Å

b = 15.1772 (6) Å

c = 5.6107 (2) Å

V = 726.50 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.50 mm−1

T = 296 K

0.40 × 0.30 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.835, T max = 0.905

6343 measured reflections

1285 independent reflections

1235 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.073

S = 1.10

1285 reflections

111 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.21 e Å−3

Absolute structure: Flack (1983 ▶), 503 Friedel pairs

Flack parameter: 0.10 (10)

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2 and SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812022817/bt5923sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022817/bt5923Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812022817/bt5923Isup3.cml

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

C11H10N2O2+·2ClO4−	Dx = 1.760 Mg m−3
Mr = 385.11	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P21212	Cell parameters from 256 reflections
a = 8.5315 (3) Å	θ = 2.3–26.2°
b = 15.1772 (6) Å	µ = 0.50 mm−1
c = 5.6107 (2) Å	T = 296 K
V = 726.50 (5) Å3	Block, colorless
Z = 2	0.40 × 0.30 × 0.20 mm
F(000) = 392

Bruker APEXII CCD area-detector diffractometer	1285 independent reflections
Radiation source: fine-focus sealed tube	1235 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
ω scans	θmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −10→10
Tmin = 0.835, Tmax = 0.905	k = −18→16
6343 measured reflections	l = −6→6

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.028	w = 1/[σ2(Fo2) + (0.0315P)2 + 0.4015P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.073	(Δ/σ)max < 0.001
S = 1.10	Δρmax = 0.34 e Å−3
1285 reflections	Δρmin = −0.21 e Å−3
111 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.019 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 503 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.10 (10)

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 > 2σ(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	0.1257 (3)	0.13417 (17)	0.4051 (5)	0.0416 (6)
H1	0.0408	0.1642	0.3402	0.050*
C2	0.1807 (3)	0.05924 (17)	0.2988 (4)	0.0372 (6)
H2	0.1340	0.0381	0.1604	0.045*
C3	0.3062 (3)	0.01520 (14)	0.3985 (4)	0.0317 (5)
H3	0.3449	−0.0357	0.3274	0.038*
C4	0.3745 (3)	0.04756 (14)	0.6063 (4)	0.0287 (5)
C5	0.3158 (3)	0.12400 (15)	0.7048 (4)	0.0334 (5)
H5	0.3609	0.1474	0.8419	0.040*
C6	0.5000	0.0000	0.7390 (6)	0.0308 (7)
N1	0.1948 (2)	0.16399 (13)	0.6032 (4)	0.0386 (5)
H7	0.1591	0.2113	0.6677	0.046*
O1	0.5000	0.0000	0.9548 (4)	0.0431 (6)
Cl1	0.30796 (6)	0.32979 (4)	1.13244 (10)	0.03518 (19)
O2	0.2552 (3)	0.31908 (15)	0.8930 (4)	0.0720 (7)
O3	0.1779 (3)	0.33349 (15)	1.2909 (4)	0.0647 (6)
O4	0.4064 (2)	0.25628 (13)	1.1946 (4)	0.0539 (6)
O5	0.3940 (3)	0.41004 (13)	1.1460 (5)	0.0622 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0318 (12)	0.0470 (14)	0.0461 (16)	0.0021 (11)	−0.0001 (12)	0.0095 (13)
C2	0.0350 (13)	0.0444 (14)	0.0323 (12)	−0.0082 (12)	−0.0038 (11)	0.0022 (10)
C3	0.0339 (11)	0.0321 (12)	0.0293 (11)	−0.0041 (10)	0.0037 (12)	−0.0010 (10)
C4	0.0293 (11)	0.0299 (11)	0.0269 (11)	−0.0019 (9)	0.0043 (11)	0.0025 (10)
C5	0.0348 (12)	0.0336 (12)	0.0319 (12)	−0.0013 (11)	0.0021 (11)	−0.0022 (9)
C6	0.0346 (18)	0.0289 (17)	0.0288 (18)	−0.0017 (15)	0.000	0.000
N1	0.0378 (10)	0.0327 (10)	0.0452 (12)	0.0081 (10)	0.0046 (10)	−0.0007 (10)
O1	0.0499 (15)	0.0537 (16)	0.0259 (13)	0.0073 (14)	0.000	0.000
Cl1	0.0335 (3)	0.0328 (3)	0.0393 (3)	−0.0005 (2)	0.0001 (3)	−0.0034 (3)
O2	0.0990 (17)	0.0660 (14)	0.0511 (12)	0.0026 (13)	−0.0214 (12)	−0.0129 (12)
O3	0.0620 (13)	0.0551 (12)	0.0770 (15)	0.0139 (12)	0.0314 (11)	0.0109 (12)
O4	0.0398 (10)	0.0402 (10)	0.0817 (16)	0.0070 (8)	−0.0062 (10)	−0.0008 (10)
O5	0.0604 (12)	0.0403 (11)	0.0858 (16)	−0.0138 (9)	−0.0075 (14)	0.0029 (12)

C1—N1	1.337 (3)	C5—N1	1.327 (3)
C1—C2	1.368 (4)	C5—H5	0.9300
C1—H1	0.9300	C6—O1	1.210 (4)
C2—C3	1.381 (4)	C6—C4i	1.491 (3)
C2—H2	0.9300	N1—H7	0.8600
C3—C4	1.393 (3)	Cl1—O3	1.423 (2)
C3—H3	0.9300	Cl1—O5	1.4242 (19)
C4—C5	1.379 (3)	Cl1—O2	1.426 (2)
C4—C6	1.491 (3)	Cl1—O4	1.439 (2)
N1—C1—C2	119.5 (2)	C4—C5—H5	120.2
N1—C1—H1	120.2	O1—C6—C4	119.97 (14)
C2—C1—H1	120.2	O1—C6—C4i	119.97 (14)
C1—C2—C3	119.5 (2)	C4—C6—C4i	120.1 (3)
C1—C2—H2	120.3	C5—N1—C1	123.1 (2)
C3—C2—H2	120.3	C5—N1—H7	118.5
C2—C3—C4	119.5 (2)	C1—N1—H7	118.5
C2—C3—H3	120.2	O3—Cl1—O5	109.56 (14)
C4—C3—H3	120.2	O3—Cl1—O2	110.31 (16)
C5—C4—C3	118.7 (2)	O5—Cl1—O2	108.08 (15)
C5—C4—C6	117.9 (2)	O3—Cl1—O4	109.53 (13)
C3—C4—C6	123.2 (2)	O5—Cl1—O4	110.44 (12)
N1—C5—C4	119.7 (2)	O2—Cl1—O4	108.90 (14)
N1—C5—H5	120.2
N1—C1—C2—C3	0.4 (4)	C5—C4—C6—O1	34.0 (2)
C1—C2—C3—C4	0.2 (3)	C3—C4—C6—O1	−141.03 (17)
C2—C3—C4—C5	−1.0 (3)	C5—C4—C6—C4i	−146.0 (2)
C2—C3—C4—C6	174.0 (2)	C3—C4—C6—C4i	38.97 (17)
C3—C4—C5—N1	1.2 (3)	C4—C5—N1—C1	−0.6 (4)
C6—C4—C5—N1	−174.1 (2)	C2—C1—N1—C5	−0.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H7···O2	0.86	2.22	2.907 (3)	136
N1ii—H7ii···O4	0.86	2.34	2.967 (2)	130

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H7⋯O2	0.86	2.22	2.907 (3)	136
N1i—H7i⋯O4	0.86	2.34	2.967 (2)	130

Symmetry code: (i) .