Bis(2,6-dicarboxy­pyridinium) dichloride acetone monosolvate

Ton, C.Q.; Bolte, M.

doi:10.1107/S1600536809043220

organic compounds

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Volume 65| Part 11| November 2009| Page o2848

https://doi.org/10.1107/S1600536809043220

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Bis(2,6-dicarboxypyridinium) dichloride acetone monosolvate

Cuong Quoc Ton ^a and Michael Bolte ^b ^*

^aInstitut für Organische Chemie der Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, D-60438 Frankfurt am Main, Germany, and ^bInstitut für Anorganische Chemie der Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, D-60438 Frankfurt am Main, Germany
^*Correspondence e-mail: bolte@chemie.uni-frankfurt.de

(Received 20 October 2009; accepted 20 October 2009; online 23 October 2009)

The title compound, 2C₇H₆NO₄⁺·2Cl⁻·C₃H₆O, crystallizes with two 2,6-dicarboxypyridinium cations, two chloride anions and one acetone molecule 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_r = 465.23
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.028
wR(F²) = 0.082
S = 1.07
3867 reflections
277 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.33 e Å⁻³

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) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x, y, z-1.

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.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809043220/ng2671Isup2.hkl

checkCIF report

Comment top

The aim of our research is the cocrystallization of two small organic compounds in order to examine the hydrogen bonds formed between hydrogen-bond acceptors and hydrogen-bond donors (Ton & Bolte, 2005; Tutughamiarso et al., 2009). When pyridine-2,6-dicarbonyl dichlorid and resorcinol were mixed in order to obtain a hydrogen bonded supermolecular complex, it turned out that the pyridine-2,6-dicarbonyl dichlorid had been hydrolyzed to the dicarboxylic acid. The title compound crystallizes with two 2,6-dicarboxypyridinium cations, two chloride anions and one acetone molecule in the asymmetric unit. The crystal structure is characterized by alternating cations and by Cl^- anions forming zigzag chains running along the a axis. The amino H atoms do not form intermolecular hydrogen bonds, but show short distances to the O atoms of the adjacent carboxyl groups.

Related literature top

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

Experimental top

Pyridine-2,6-dicarbonyl dichlorid (20 mg) and resorcinol (20 mg) were dissolved in 2 ml absolute acetone. The mixture was sealed and set aside at room temperature. After two weeks small block-shaped crystals were obtained. It turned out that the pyridine-2,6-dicarbonyl dichloride had been hydrolyzed to the dicarboxylic acid.

Structure description top

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

Computing details top

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

Figures top

	Fig. 1. A view of the molecular structure of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. Part of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines.

Bis(2,6-dicarboxypyridinium) dichloride acetone monosolvate top

Crystal data top

2C₇H₆NO₄⁺·2Cl⁻·C₃H₆O	F(000) = 960
M_r = 465.23	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0611P)²] where P = (F_o² + 2F_c²)/3
3867 reflections	(Δ/σ)_max = 0.001
277 parameters	Δρ_max = 0.17 e Å⁻³
2 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

2C₇H₆NO₄⁺·2Cl⁻·C₃H₆O	V = 2046.0 (7) Å³
M_r = 465.23	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 21.108 (4) Å	µ = 0.37 mm⁻¹
b = 6.7877 (14) Å	T = 173 K
c = 15.224 (3) Å	0.30 × 0.20 × 0.20 mm
β = 110.28 (3)°

Data collection top

Stoe IPDSII two-circle diffractometer	3867 independent reflections
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995)	3412 reflections with I > 2σ(I)
T_min = 0.897, T_max = 0.930	R_int = 0.041
27731 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	2 restraints
wR(F²) = 0.082	H-atom parameters constrained
S = 1.07	Δρ_max = 0.17 e Å⁻³
3867 reflections	Δρ_min = −0.33 e Å⁻³
277 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, y−1/2, −z+1/2; (ii) −x+2, y+1/2, −z+1/2; (iii) x, y, z−1.

Experimental details

Crystal data
Chemical formula	2C₇H₆NO₄⁺·2Cl⁻·C₃H₆O
M_r	465.23
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	21.108 (4), 6.7877 (14), 15.224 (3)
β (°)	110.28 (3)
V (Å³)	2046.0 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.37
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Stoe IPDSII two-circle
Absorption correction	Multi-scan (MULABS; Spek, 2003; Blessing, 1995)
T_min, T_max	0.897, 0.930
No. of measured, independent and observed [I > 2σ(I)] reflections	27731, 3867, 3412
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.082, 1.07
No. of reflections	3867
No. of parameters	277
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.33

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···Cl2ⁱ	0.84	2.11	2.9469 (13)	170.8
O3—H3···Cl1ⁱⁱ	0.84	2.14	2.9727 (13)	171.5
O12—H12···Cl1	0.84	2.13	2.9696 (15)	179.3
O14—H14···Cl2	0.84	2.14	2.9775 (12)	177.2
N1—H1N···O30ⁱⁱⁱ	0.88	2.42	3.277 (2)	166.3
N1—H1N···O2	0.88	2.34	2.6685 (16)	102.5
N1—H1N···O4	0.88	2.39	2.7195 (16)	102.8
N2—H2N···O11	0.88	2.25	2.6365 (17)	106.2
N2—H2N···O13	0.88	2.26	2.6392 (16)	105.9

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+2, y+1/2, −z+1/2; (iii) x, y, z−1.

References

Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany. Google Scholar
Ton, Q. C. & Bolte, M. (2005). Acta Cryst. E61, o1406–o1407. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Tutughamiarso, M., Bolte, M. & Egert, E. (2009). Acta Cryst. C65, o574–o578. Web of Science CSD CrossRef IUCr Journals Google Scholar

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