Bis(2,6-dicarboxy-pyridinium) dichloride acetone monosolvate.

The title compound, 2C(7)H(6)NO(4) (+)·2Cl(-)·C(3)H(6)O, crystallizes with two 2,6-dicarboxy-pyridinium cations, two chloride anions and one acetone mol-ecule in the asymmetric unit. The crystal structure is characterized by alternating cations and by Cl(-) anions, forming zigzag chains running along the a axis.

Related literature

For co-crystallization experiments, see: Ton & Bolte (2005 ▶); Tutughamiarso et al. (2009 ▶).

Experimental

Crystal data

2C7H6NO4 +·2Cl−·C3H6O

M = 465.23

Monoclinic,

a = 21.108 (4) Å

b = 6.7877 (14) Å

c = 15.224 (3) Å

β = 110.28 (3)°

V = 2046.0 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.37 mm−1

T = 173 K

0.30 × 0.20 × 0.20 mm

Data collection

Stoe IPDSII two-circle diffractometer

Absorption correction: multi-scan (MULABS; Spek, 2003 ▶; Blessing, 1995 ▶) T min = 0.897, T max = 0.930

27731 measured reflections

3867 independent reflections

3412 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.082

S = 1.07

3867 reflections

277 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.33 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809043220/ng2671sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043220/ng2671Isup2.hkl

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

2C7H6NO4+·2Cl−·C3H6O	F(000) = 960
Mr = 465.23	Dx = 1.510 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4736 reflections
a = 21.108 (4) Å	θ = 3.6–23.9°
b = 6.7877 (14) Å	µ = 0.37 mm−1
c = 15.224 (3) Å	T = 173 K
β = 110.28 (3)°	Block, colourless
V = 2046.0 (7) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Stoe IPDSII two-circle diffractometer	3867 independent reflections
Radiation source: fine-focus sealed tube	3412 reflections with I > 2σ(I)
graphite	Rint = 0.041
ω scans	θmax = 25.7°, θmin = 2.7°
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	h = −25→25
Tmin = 0.897, Tmax = 0.930	k = −8→8
27731 measured reflections	l = −18→18

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0611P)2] where P = (Fo2 + 2Fc2)/3
3867 reflections	(Δ/σ)max = 0.001
277 parameters	Δρmax = 0.17 e Å−3
2 restraints	Δρmin = −0.33 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
Cl2	0.400074 (15)	0.86812 (5)	0.57272 (2)	0.02093 (10)
N1	0.86727 (6)	0.62429 (16)	0.08751 (8)	0.0176 (2)
H1N	0.8461	0.6094	0.0269	0.021*
O1	0.72464 (5)	0.5375 (2)	0.15456 (8)	0.0373 (3)
O2	0.74328 (5)	0.47101 (18)	0.02079 (7)	0.0314 (3)
H2	0.7020	0.4421	0.0003	0.047*
O3	1.02593 (5)	0.77466 (16)	0.07980 (7)	0.0269 (2)
H3	1.0420	0.7892	0.0369	0.040*
O4	0.93315 (5)	0.66689 (17)	−0.03641 (7)	0.0312 (3)
C1	0.93284 (6)	0.67693 (19)	0.11849 (9)	0.0185 (3)
C2	0.96772 (7)	0.6960 (2)	0.21350 (10)	0.0225 (3)
H2A	1.0144	0.7289	0.2358	0.027*
C3	0.93390 (8)	0.6665 (2)	0.27580 (10)	0.0259 (3)
H3A	0.9572	0.6793	0.3413	0.031*
C4	0.86538 (7)	0.6179 (2)	0.24171 (10)	0.0234 (3)
H4	0.8412	0.6016	0.2835	0.028*
C5	0.83310 (7)	0.59365 (19)	0.14648 (9)	0.0194 (3)
C6	0.76021 (7)	0.5313 (2)	0.10756 (10)	0.0224 (3)
C7	0.96393 (7)	0.7065 (2)	0.04423 (9)	0.0210 (3)
C11	0.55437 (6)	0.66485 (18)	0.39734 (9)	0.0170 (3)
C12	0.52686 (7)	0.65541 (19)	0.30102 (9)	0.0194 (3)
H12A	0.4804	0.6830	0.2695	0.023*
C13	0.56847 (7)	0.6047 (2)	0.25084 (9)	0.0220 (3)
H13	0.5505	0.6010	0.1844	0.026*
C14	0.63629 (7)	0.5591 (2)	0.29749 (9)	0.0202 (3)
H14A	0.6647	0.5235	0.2635	0.024*
C15	0.66136 (6)	0.56671 (19)	0.39429 (9)	0.0173 (3)
C16	0.73154 (6)	0.51806 (19)	0.45933 (9)	0.0201 (3)
C17	0.51949 (6)	0.71815 (19)	0.46516 (9)	0.0189 (3)
N2	0.62003 (6)	0.62153 (15)	0.43989 (7)	0.0162 (2)
H2N	0.6370	0.6296	0.5014	0.019*
O11	0.74741 (5)	0.55571 (16)	0.54219 (7)	0.0281 (2)
O12	0.76850 (5)	0.43135 (16)	0.41724 (7)	0.0260 (2)
H12	0.8064	0.4033	0.4568	0.039*
O13	0.54906 (5)	0.69891 (16)	0.54842 (7)	0.0269 (2)
O14	0.45750 (5)	0.78176 (16)	0.42371 (7)	0.0244 (2)
H14	0.4400	0.8075	0.4643	0.037*
O30	0.77087 (6)	0.63026 (17)	0.86620 (9)	0.0391 (3)
C31	0.81624 (8)	0.4065 (2)	0.78336 (11)	0.0325 (3)
H31A	0.8598	0.4523	0.8271	0.049*
H31B	0.8139	0.4325	0.7190	0.049*
H31C	0.8118	0.2646	0.7917	0.049*
C32	0.76014 (7)	0.5135 (2)	0.80203 (11)	0.0271 (3)
C33	0.68937 (8)	0.4701 (3)	0.73731 (13)	0.0398 (4)
H33A	0.6597	0.4538	0.7741	0.060*
H33B	0.6893	0.3488	0.7024	0.060*
H33C	0.6730	0.5797	0.6933	0.060*
Cl1	0.903216 (16)	0.33503 (5)	0.55619 (2)	0.02480 (11)

	U11	U22	U33	U12	U13	U23
Cl2	0.01679 (17)	0.02369 (18)	0.02316 (18)	0.00153 (11)	0.00802 (13)	0.00127 (12)
N1	0.0179 (5)	0.0192 (5)	0.0153 (5)	0.0008 (4)	0.0052 (4)	−0.0010 (4)
O1	0.0271 (6)	0.0621 (8)	0.0297 (6)	−0.0071 (5)	0.0188 (5)	−0.0038 (5)
O2	0.0185 (5)	0.0508 (7)	0.0265 (6)	−0.0076 (5)	0.0098 (4)	−0.0110 (5)
O3	0.0157 (5)	0.0409 (6)	0.0248 (5)	−0.0049 (4)	0.0080 (4)	−0.0054 (4)
O4	0.0253 (5)	0.0496 (7)	0.0185 (5)	−0.0122 (5)	0.0074 (4)	−0.0023 (4)
C1	0.0176 (6)	0.0170 (6)	0.0206 (7)	0.0017 (5)	0.0064 (5)	−0.0001 (5)
C2	0.0196 (6)	0.0250 (7)	0.0207 (7)	0.0006 (5)	0.0042 (5)	−0.0020 (5)
C3	0.0285 (7)	0.0303 (7)	0.0164 (7)	0.0018 (6)	0.0047 (6)	−0.0015 (5)
C4	0.0275 (7)	0.0262 (7)	0.0191 (7)	0.0017 (5)	0.0115 (6)	0.0005 (5)
C5	0.0215 (7)	0.0174 (6)	0.0214 (7)	0.0026 (5)	0.0100 (5)	0.0012 (5)
C6	0.0222 (7)	0.0246 (7)	0.0222 (7)	0.0008 (5)	0.0101 (5)	0.0018 (5)
C7	0.0179 (6)	0.0233 (7)	0.0215 (7)	−0.0013 (5)	0.0065 (5)	−0.0008 (5)
C11	0.0175 (6)	0.0152 (6)	0.0188 (6)	−0.0004 (5)	0.0071 (5)	−0.0003 (5)
C12	0.0192 (6)	0.0187 (6)	0.0184 (6)	−0.0003 (5)	0.0039 (5)	0.0011 (5)
C13	0.0278 (7)	0.0220 (7)	0.0156 (6)	−0.0015 (5)	0.0070 (5)	0.0001 (5)
C14	0.0242 (7)	0.0201 (6)	0.0194 (6)	−0.0006 (5)	0.0117 (5)	−0.0003 (5)
C15	0.0186 (6)	0.0146 (6)	0.0202 (6)	−0.0011 (5)	0.0087 (5)	−0.0005 (5)
C16	0.0196 (6)	0.0196 (6)	0.0219 (7)	0.0005 (5)	0.0082 (5)	−0.0003 (5)
C17	0.0178 (6)	0.0201 (7)	0.0193 (6)	0.0007 (5)	0.0071 (5)	−0.0005 (5)
N2	0.0176 (5)	0.0174 (5)	0.0132 (5)	0.0004 (4)	0.0047 (4)	−0.0013 (4)
O11	0.0214 (5)	0.0392 (6)	0.0211 (5)	0.0048 (4)	0.0038 (4)	−0.0057 (4)
O12	0.0197 (5)	0.0340 (6)	0.0248 (5)	0.0084 (4)	0.0083 (4)	0.0002 (4)
O13	0.0241 (5)	0.0399 (6)	0.0174 (5)	0.0069 (4)	0.0081 (4)	−0.0004 (4)
O14	0.0188 (5)	0.0342 (6)	0.0217 (5)	0.0062 (4)	0.0091 (4)	0.0019 (4)
O30	0.0382 (6)	0.0362 (6)	0.0452 (7)	−0.0022 (5)	0.0175 (5)	−0.0108 (5)
C31	0.0323 (8)	0.0324 (8)	0.0326 (8)	0.0014 (6)	0.0111 (7)	−0.0022 (7)
C32	0.0305 (7)	0.0229 (7)	0.0288 (8)	−0.0012 (6)	0.0115 (6)	0.0049 (6)
C33	0.0292 (8)	0.0443 (10)	0.0429 (10)	0.0012 (7)	0.0087 (7)	−0.0006 (8)
Cl1	0.01629 (17)	0.02919 (19)	0.0289 (2)	0.00156 (12)	0.00780 (14)	−0.00016 (13)

N1—C1	1.3467 (17)	C13—C14	1.394 (2)
N1—C5	1.3484 (18)	C13—H13	0.9500
N1—H1N	0.8800	C14—C15	1.3834 (19)
O1—C6	1.2040 (18)	C14—H14A	0.9500
O2—C6	1.3087 (18)	C15—N2	1.3421 (17)
O2—H2	0.8400	C15—C16	1.5057 (18)
O3—C7	1.3147 (17)	C16—O11	1.2149 (17)
O3—H3	0.8400	C16—O12	1.3085 (17)
O4—C7	1.2036 (17)	C17—O13	1.2103 (17)
C1—C2	1.3829 (19)	C17—O14	1.3132 (16)
C1—C7	1.5045 (19)	N2—H2N	0.8800
C2—C3	1.385 (2)	O12—H12	0.8400
C2—H2A	0.9500	O14—H14	0.8400
C3—C4	1.396 (2)	O30—C32	1.2167 (19)
C3—H3A	0.9500	C31—C32	1.498 (2)
C4—C5	1.381 (2)	C31—H31A	0.9800
C4—H4	0.9500	C31—H31B	0.9800
C5—C6	1.5052 (19)	C31—H31C	0.9800
C11—N2	1.3433 (17)	C32—C33	1.506 (2)
C11—C12	1.3790 (19)	C33—H33A	0.9800
C11—C17	1.5052 (18)	C33—H33B	0.9800
C12—C13	1.392 (2)	C33—H33C	0.9800
C12—H12A	0.9500
C1—N1—C5	121.98 (11)	C14—C13—H13	119.8
C1—N1—H1N	119.0	C15—C14—C13	118.71 (12)
C5—N1—H1N	119.0	C15—C14—H14A	120.6
C6—O2—H2	109.5	C13—C14—H14A	120.6
C7—O3—H3	109.5	N2—C15—C14	118.96 (12)
N1—C1—C2	120.07 (13)	N2—C15—C16	112.85 (11)
N1—C1—C7	115.80 (12)	C14—C15—C16	128.19 (12)
C2—C1—C7	124.11 (12)	O11—C16—O12	127.34 (12)
C1—C2—C3	119.26 (13)	O11—C16—C15	119.41 (12)
C1—C2—H2A	120.4	O12—C16—C15	113.22 (12)
C3—C2—H2A	120.4	O13—C17—O14	127.23 (12)
C2—C3—C4	119.53 (13)	O13—C17—C11	119.68 (12)
C2—C3—H3A	120.2	O14—C17—C11	113.10 (11)
C4—C3—H3A	120.2	C15—N2—C11	123.93 (11)
C5—C4—C3	119.25 (13)	C15—N2—H2N	118.0
C5—C4—H4	120.4	C11—N2—H2N	118.0
C3—C4—H4	120.4	C16—O12—H12	109.5
N1—C5—C4	119.83 (12)	C17—O14—H14	109.5
N1—C5—C6	119.40 (12)	C32—C31—H31A	109.5
C4—C5—C6	120.77 (13)	C32—C31—H31B	109.5
O1—C6—O2	127.04 (13)	H31A—C31—H31B	109.5
O1—C6—C5	121.27 (13)	C32—C31—H31C	109.5
O2—C6—C5	111.69 (12)	H31A—C31—H31C	109.5
O4—C7—O3	127.38 (13)	H31B—C31—H31C	109.5
O4—C7—C1	120.99 (12)	O30—C32—C31	121.94 (14)
O3—C7—C1	111.63 (12)	O30—C32—C33	121.25 (15)
N2—C11—C12	119.10 (12)	C31—C32—C33	116.81 (14)
N2—C11—C17	112.96 (11)	C32—C33—H33A	109.5
C12—C11—C17	127.94 (12)	C32—C33—H33B	109.5
C11—C12—C13	118.80 (12)	H33A—C33—H33B	109.5
C11—C12—H12A	120.6	C32—C33—H33C	109.5
C13—C12—H12A	120.6	H33A—C33—H33C	109.5
C12—C13—C14	120.46 (12)	H33B—C33—H33C	109.5
C12—C13—H13	119.8
C5—N1—C1—C2	1.76 (19)	N2—C11—C12—C13	−1.17 (19)
C5—N1—C1—C7	−179.77 (12)	C17—C11—C12—C13	179.30 (12)
N1—C1—C2—C3	−2.1 (2)	C11—C12—C13—C14	1.71 (19)
C7—C1—C2—C3	179.60 (13)	C12—C13—C14—C15	−0.4 (2)
C1—C2—C3—C4	0.1 (2)	C13—C14—C15—N2	−1.37 (19)
C2—C3—C4—C5	2.1 (2)	C13—C14—C15—C16	177.90 (12)
C1—N1—C5—C4	0.54 (19)	N2—C15—C16—O11	−9.64 (18)
C1—N1—C5—C6	−178.85 (11)	C14—C15—C16—O11	171.05 (13)
C3—C4—C5—N1	−2.5 (2)	N2—C15—C16—O12	168.43 (11)
C3—C4—C5—C6	176.92 (12)	C14—C15—C16—O12	−10.9 (2)
N1—C5—C6—O1	−166.16 (14)	N2—C11—C17—O13	−7.56 (18)
C4—C5—C6—O1	14.5 (2)	C12—C11—C17—O13	172.00 (13)
N1—C5—C6—O2	14.67 (18)	N2—C11—C17—O14	172.82 (11)
C4—C5—C6—O2	−164.72 (13)	C12—C11—C17—O14	−7.62 (19)
N1—C1—C7—O4	−6.70 (19)	C14—C15—N2—C11	2.01 (19)
C2—C1—C7—O4	171.71 (14)	C16—C15—N2—C11	−177.37 (11)
N1—C1—C7—O3	174.26 (11)	C12—C11—N2—C15	−0.71 (19)
C2—C1—C7—O3	−7.33 (19)	C17—C11—N2—C15	178.89 (11)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···Cl2i	0.84	2.11	2.9469 (13)	171
O3—H3···Cl1ii	0.84	2.14	2.9727 (13)	172
O12—H12···Cl1	0.84	2.13	2.9696 (15)	179
O14—H14···Cl2	0.84	2.14	2.9775 (12)	177
N1—H1N···O30iii	0.88	2.42	3.277 (2)	166
N1—H1N···O2	0.88	2.34	2.6685 (16)	103
N1—H1N···O4	0.88	2.39	2.7195 (16)	103
N2—H2N···O11	0.88	2.25	2.6365 (17)	106
N2—H2N···O13	0.88	2.26	2.6392 (16)	106

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯Cl2i	0.84	2.11	2.9469 (13)	171
O3—H3⋯Cl1ii	0.84	2.14	2.9727 (13)	172
O12—H12⋯Cl1	0.84	2.13	2.9696 (15)	179
O14—H14⋯Cl2	0.84	2.14	2.9775 (12)	177
N1—H1N⋯O30iii	0.88	2.42	3.277 (2)	166
N1—H1N⋯O2	0.88	2.34	2.6685 (16)	103
N1—H1N⋯O4	0.88	2.39	2.7195 (16)	103
N2—H2N⋯O11	0.88	2.25	2.6365 (17)	106
N2—H2N⋯O13	0.88	2.26	2.6392 (16)	106

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