1,1'-(Ethane-1,2-di-yl)dipyridinium dichromate(VI).

In the cation of the title salt, (C(12)H(14)N(2))[Cr(2)O(7)], the two pyridinium moieties are in an anti orientation with respect to one another. The dihedral angle between the pyridine rings is 6.3 (2)°. The N-C-C-N torsion angle is 177.5 (2)°. In the dianion, the Cr(VI) ions are in a slightly distorted tetra-hedral coordination environment and the bond angles at the independent Cr(VI) ions are in the ranges 105.93 (10)-110.60 (11) and 107.35 (11)-111.07 (12)°. The Cr-O-Cr angle is 127.96 (12)°. The crystal used was an inversion twin with refined components of 0.510 (19) and 0.490 (19).

Related literature

For the crystal structures of the salts with formula [C5H5NCH2CH2NC5H5]2+·2X − [X − = IO3 −, IO4 −], the preparation of 1,1′-(ethane-1,2-di­yl)dipyridinium dibromide and the orientation of pyridine moieties, see: Gholizadeh, Maleki et al. (2011 ▶); Gholizadeh, Hojati et al. (2011 ▶). For dichromate salts, see: Lennartson & Håkansson (2009 ▶); Averbuch-Pouchot et al. (1984 ▶).

Experimental

Crystal data

(C12H14N2)[Cr2O7]

M = 402.25

Monoclinic,

a = 8.2882 (4) Å

b = 9.0722 (4) Å

c = 10.0179 (5) Å

β = 91.882 (1)°

V = 752.86 (6) Å3

Z = 2

Mo Kα radiation

μ = 1.48 mm−1

T = 100 K

0.22 × 0.15 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.737, T max = 0.808

5446 measured reflections

2628 independent reflections

2546 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.067

S = 1.04

2628 reflections

209 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.21 e Å−3

Absolute structure: Flack (1983 ▶), 1163 Friedel pairs

Flack parameter: 0.510 (19)

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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 enCIFer (Allen et al., 2004 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812005430/lh5410sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005430/lh5410Isup2.hkl

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

(C12H14N2)[Cr2O7]	F(000) = 408
Mr = 402.25	Dx = 1.774 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3255 reflections
a = 8.2882 (4) Å	θ = 2.5–26.5°
b = 9.0722 (4) Å	µ = 1.48 mm−1
c = 10.0179 (5) Å	T = 100 K
β = 91.882 (1)°	Block, orange
V = 752.86 (6) Å3	0.22 × 0.15 × 0.15 mm
Z = 2

Bruker APEXII CCD diffractometer	2628 independent reflections
Radiation source: fine-focus sealed tube	2546 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 25.3°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→9
Tmin = 0.737, Tmax = 0.808	k = −10→10
5446 measured reflections	l = −12→12

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.027	H-atom parameters constrained
wR(F2) = 0.067	w = 1/[σ2(Fo2) + (0.0332P)2 + 0.2849P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
2628 reflections	Δρmax = 0.47 e Å−3
209 parameters	Δρmin = −0.21 e Å−3
1 restraint	Absolute structure: Flack (1983), 1163 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.510 (19)

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
Cr1	0.65538 (5)	0.04259 (4)	0.83530 (4)	0.01584 (13)
Cr2	0.35152 (5)	−0.03987 (5)	0.64354 (4)	0.01691 (13)
O1	0.7936 (2)	0.0097 (2)	0.7300 (2)	0.0250 (5)
O2	0.7001 (2)	0.1896 (2)	0.9204 (2)	0.0230 (5)
O3	0.6343 (3)	−0.0968 (2)	0.9351 (2)	0.0241 (5)
O4	0.4684 (3)	0.0804 (2)	0.7502 (2)	0.0255 (5)
O5	0.2177 (3)	−0.1216 (3)	0.7304 (2)	0.0312 (6)
O6	0.4687 (3)	−0.1613 (2)	0.5775 (2)	0.0251 (5)
O7	0.2677 (3)	0.0602 (3)	0.5277 (2)	0.0294 (5)
N1	0.2884 (3)	0.3914 (3)	0.6933 (2)	0.0177 (6)
N2	0.6566 (3)	0.5863 (3)	0.8330 (2)	0.0165 (6)
C1	0.1985 (4)	0.3157 (4)	0.7779 (3)	0.0207 (7)
H1	0.2448	0.2834	0.8608	0.025*
C2	0.0391 (4)	0.2840 (3)	0.7460 (3)	0.0213 (7)
H2	−0.0241	0.2291	0.8058	0.026*
C3	−0.0274 (4)	0.3334 (4)	0.6255 (3)	0.0218 (7)
H3	−0.1367	0.3118	0.6015	0.026*
C4	0.0658 (4)	0.4138 (4)	0.5407 (3)	0.0224 (7)
H4	0.0204	0.4503	0.4589	0.027*
C5	0.2256 (4)	0.4412 (4)	0.5753 (3)	0.0208 (7)
H5	0.2913	0.4949	0.5164	0.025*
C6	0.4621 (4)	0.4188 (3)	0.7282 (3)	0.0193 (7)
H6A	0.5255	0.4160	0.6461	0.023*
H6B	0.5033	0.3406	0.7891	0.023*
C7	0.4825 (3)	0.5674 (4)	0.7949 (3)	0.0192 (7)
H7A	0.4468	0.6467	0.7328	0.023*
H7B	0.4164	0.5724	0.8753	0.023*
C8	0.7158 (3)	0.5188 (3)	0.9456 (3)	0.0179 (6)
H8	0.6471	0.4605	0.9983	0.022*
C9	0.8761 (4)	0.5360 (4)	0.9823 (3)	0.0217 (6)
H9	0.9189	0.4901	1.0611	0.026*
C10	0.9750 (4)	0.6206 (4)	0.9038 (3)	0.0219 (7)
H10	1.0858	0.6328	0.9285	0.026*
C11	0.9116 (4)	0.6876 (4)	0.7886 (3)	0.0197 (7)
H11	0.9783	0.7456	0.7339	0.024*
C12	0.7493 (4)	0.6681 (4)	0.7551 (3)	0.0197 (7)
H12	0.7039	0.7129	0.6768	0.024*

	U11	U22	U33	U12	U13	U23
Cr1	0.0149 (2)	0.0163 (3)	0.0162 (2)	0.0001 (2)	−0.00137 (17)	−0.0007 (2)
Cr2	0.0149 (2)	0.0192 (3)	0.0165 (2)	−0.0025 (2)	−0.00182 (17)	0.0006 (2)
O1	0.0229 (11)	0.0267 (13)	0.0256 (11)	−0.0042 (9)	0.0042 (9)	−0.0029 (10)
O2	0.0232 (12)	0.0214 (12)	0.0239 (13)	0.0036 (9)	−0.0064 (9)	−0.0039 (10)
O3	0.0295 (12)	0.0219 (12)	0.0210 (11)	0.0040 (10)	0.0034 (9)	0.0030 (10)
O4	0.0215 (11)	0.0208 (12)	0.0333 (13)	−0.0003 (9)	−0.0105 (9)	−0.0024 (10)
O5	0.0265 (13)	0.0378 (15)	0.0296 (13)	−0.0101 (11)	0.0055 (10)	−0.0017 (11)
O6	0.0278 (12)	0.0271 (13)	0.0206 (11)	0.0027 (10)	0.0020 (9)	−0.0025 (10)
O7	0.0308 (12)	0.0277 (13)	0.0289 (11)	0.0000 (10)	−0.0100 (9)	0.0036 (11)
N1	0.0158 (13)	0.0200 (14)	0.0172 (12)	0.0023 (11)	−0.0016 (10)	−0.0032 (11)
N2	0.0164 (13)	0.0161 (14)	0.0171 (12)	0.0004 (10)	0.0018 (10)	−0.0037 (11)
C1	0.0259 (17)	0.0168 (16)	0.0189 (15)	0.0023 (14)	−0.0047 (12)	−0.0011 (14)
C2	0.0220 (16)	0.0193 (16)	0.0227 (16)	−0.0006 (13)	0.0002 (12)	0.0022 (14)
C3	0.0180 (16)	0.0227 (17)	0.0242 (16)	0.0007 (13)	−0.0032 (12)	−0.0044 (14)
C4	0.0187 (16)	0.0319 (19)	0.0167 (14)	0.0066 (14)	−0.0010 (12)	0.0004 (14)
C5	0.0230 (16)	0.0236 (18)	0.0160 (14)	0.0010 (14)	0.0025 (11)	0.0007 (14)
C6	0.0151 (14)	0.0199 (16)	0.0226 (15)	0.0003 (12)	−0.0034 (12)	−0.0034 (13)
C7	0.0148 (15)	0.0204 (16)	0.0224 (15)	0.0001 (13)	0.0002 (11)	0.0009 (14)
C8	0.0228 (15)	0.0164 (16)	0.0147 (14)	−0.0005 (13)	0.0029 (11)	−0.0033 (12)
C9	0.0294 (16)	0.0213 (16)	0.0142 (13)	0.0052 (15)	−0.0021 (11)	−0.0054 (14)
C10	0.0174 (15)	0.0215 (17)	0.0267 (17)	0.0018 (14)	−0.0025 (12)	−0.0098 (15)
C11	0.0198 (15)	0.0161 (15)	0.0234 (17)	−0.0040 (12)	0.0037 (12)	−0.0034 (13)
C12	0.0241 (17)	0.0182 (16)	0.0169 (15)	−0.0010 (14)	0.0009 (12)	−0.0027 (13)

Cr1—O1	1.611 (2)	C3—H3	0.9500
Cr1—O2	1.620 (2)	C4—C5	1.380 (4)
Cr1—O3	1.624 (2)	C4—H4	0.9500
Cr1—O4	1.777 (2)	C5—H5	0.9500
Cr2—O5	1.612 (2)	C6—C7	1.511 (4)
Cr2—O7	1.613 (2)	C6—H6A	0.9900
Cr2—O6	1.624 (2)	C6—H6B	0.9900
Cr2—O4	1.790 (2)	C7—H7A	0.9900
N1—C1	1.337 (4)	C7—H7B	0.9900
N1—C5	1.353 (4)	C8—C9	1.376 (4)
N1—C6	1.491 (4)	C8—H8	0.9500
N2—C12	1.338 (4)	C9—C10	1.386 (4)
N2—C8	1.361 (4)	C9—H9	0.9500
N2—C7	1.491 (3)	C10—C11	1.392 (4)
C1—C2	1.379 (4)	C10—H10	0.9500
C1—H1	0.9500	C11—C12	1.387 (4)
C2—C3	1.385 (4)	C11—H11	0.9500
C2—H2	0.9500	C12—H12	0.9500
C3—C4	1.376 (5)
O1—Cr1—O2	110.01 (11)	N1—C5—C4	119.8 (3)
O1—Cr1—O3	110.60 (11)	N1—C5—H5	120.1
O2—Cr1—O3	110.15 (11)	C4—C5—H5	120.1
O1—Cr1—O4	110.43 (11)	N1—C6—C7	110.2 (2)
O2—Cr1—O4	105.93 (10)	N1—C6—H6A	109.6
O3—Cr1—O4	109.62 (11)	C7—C6—H6A	109.6
O5—Cr2—O7	111.07 (12)	N1—C6—H6B	109.6
O5—Cr2—O6	109.80 (13)	C7—C6—H6B	109.6
O7—Cr2—O6	109.78 (12)	H6A—C6—H6B	108.1
O5—Cr2—O4	109.08 (11)	N2—C7—C6	108.0 (2)
O7—Cr2—O4	107.35 (11)	N2—C7—H7A	110.1
O6—Cr2—O4	109.72 (10)	C6—C7—H7A	110.1
Cr1—O4—Cr2	127.96 (12)	N2—C7—H7B	110.1
C1—N1—C5	121.2 (3)	C6—C7—H7B	110.1
C1—N1—C6	119.4 (2)	H7A—C7—H7B	108.4
C5—N1—C6	119.3 (3)	N2—C8—C9	119.3 (3)
C12—N2—C8	122.4 (2)	N2—C8—H8	120.4
C12—N2—C7	119.0 (2)	C9—C8—H8	120.4
C8—N2—C7	118.7 (2)	C8—C9—C10	119.6 (3)
N1—C1—C2	120.7 (3)	C8—C9—H9	120.2
N1—C1—H1	119.7	C10—C9—H9	120.2
C2—C1—H1	119.7	C9—C10—C11	119.9 (3)
C1—C2—C3	119.0 (3)	C9—C10—H10	120.1
C1—C2—H2	120.5	C11—C10—H10	120.1
C3—C2—H2	120.5	C12—C11—C10	118.8 (3)
C4—C3—C2	119.6 (3)	C12—C11—H11	120.6
C4—C3—H3	120.2	C10—C11—H11	120.6
C2—C3—H3	120.2	N2—C12—C11	120.0 (3)
C3—C4—C5	119.6 (3)	N2—C12—H12	120.0
C3—C4—H4	120.2	C11—C12—H12	120.0
C5—C4—H4	120.2
O1—Cr1—O4—Cr2	62.94 (19)	C1—N1—C6—C7	−94.5 (3)
O2—Cr1—O4—Cr2	−177.98 (15)	C5—N1—C6—C7	86.8 (3)
O3—Cr1—O4—Cr2	−59.16 (19)	C12—N2—C7—C6	100.0 (3)
O5—Cr2—O4—Cr1	94.27 (18)	C8—N2—C7—C6	−79.6 (3)
O7—Cr2—O4—Cr1	−145.29 (16)	N1—C6—C7—N2	177.5 (2)
O6—Cr2—O4—Cr1	−26.04 (19)	C12—N2—C8—C9	0.7 (4)
C5—N1—C1—C2	1.1 (5)	C7—N2—C8—C9	−179.7 (3)
C6—N1—C1—C2	−177.6 (3)	N2—C8—C9—C10	−0.5 (5)
N1—C1—C2—C3	−0.8 (5)	C8—C9—C10—C11	0.0 (5)
C1—C2—C3—C4	−0.5 (5)	C9—C10—C11—C12	0.2 (5)
C2—C3—C4—C5	1.6 (5)	C8—N2—C12—C11	−0.5 (5)
C1—N1—C5—C4	0.0 (5)	C7—N2—C12—C11	179.9 (3)
C6—N1—C5—C4	178.7 (3)	C10—C11—C12—N2	0.1 (5)
C3—C4—C5—N1	−1.3 (5)