2-Carboxy­quinolinium–2,4,6-trinitro­benzene­sulfonate–quinolinium-2-carboxyl­ate (1/1/1)

Smith, G.; Wermuth, U.D.; White, J.M.

doi:10.1107/S1600536807062757

organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Pages o132-o133

https://doi.org/10.1107/S1600536807062757

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2-Carboxyquinolinium–2,4,6-trinitrobenzenesulfonate–quinolinium-2-carboxylate (1/1/1)

Graham Smith,^a ^* Urs D. Wermuth ^b and Jonathan M. White ^c

^aSchool of Physical and Chemical Sciences, Queensland University of Technology, GPO Box 2434, Brisbane, Queensland 4001, Australia, ^bSchool of Biomolecular and Physical Sciences, Griffith University, Nathan, Queensland 4111, Australia, and ^cBIO-21 Molecular Science and Biotechnology, University of Melbourne, Parkville, Victoria 3052, Australia
^*Correspondence e-mail: g.smith@qut.edu.au

(Received 20 November 2007; accepted 23 November 2007; online 6 December 2007)

The structure of the title adduct compound, C₁₀H₈NO₂⁺·C₆H₂N₃O₉S⁻·C₁₀H₇NO₂, from the reaction of 2,4,6-trinitrobenzenesulfonic acid (picrylsulfonic acid) with quinoline-2-carboxylic acid (quinaldic acid) in 2-propanol–water, has been determined at 130 (2) K. The cation and the adduct species form a twisted cyclic hydrogen-bonded R²₂(10) pseudo-dimer which is extended into a one-dimensional chain structure through short head-to-tail carboxylic acid O—H⋯O_carboxyl associations [O⋯O = 2.4711 (19) Å]. The picrylsulfonate anions are attached peripherally by single N—H⋯O_sulfonate hydrogen bonds [N⋯O = 2.8643 (19) Å].

Related literature

For other related picrylsulfonate and quinaldic acid structures, see: Russell & Ward (1997 ); Smith et al. (2004 ); Smith, Wermuth & Healy (2006 ); Smith, Wermuth & White (2006 ); Smith, Wermuth, Healy & White (2007 ); Smith, Wermuth & White (2007 ); Dobrzyńska & Jerzykiewicz (2004 ).

For graph-set nomenclature, see: Etter et al. (1990 ).

Experimental

Crystal data

C₁₀H₈NO₂⁺·C₆H₂N₃O₉S⁻·C₁₀H₇NO₂
M_r = 639.51
Triclinic, $[P \overline 1]$
a = 7.8872 (6) Å
b = 12.4753 (10) Å
c = 14.6617 (12) Å
α = 66.227 (1)°
β = 74.997 (2)°
γ = 82.191 (2)°
V = 1274.42 (18) Å³
Z = 2
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 130 (2) K
0.40 × 0.30 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1999 ) T_min = 0.93, T_max = 0.98
6761 measured reflections
4446 independent reflections
3779 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.090
S = 1.00
4446 reflections
419 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1A⋯O21A	0.87 (2)	2.31 (2)	2.690 (2)	106.3 (18)
N1A—H1A⋯O21B	0.87 (2)	1.94 (2)	2.761 (2)	155 (2)
N1B—H1B⋯O13	0.85 (2)	2.23 (2)	2.8643 (19)	132 (2)
N1B—H1B⋯O21A	0.85 (2)	2.14 (3)	2.746 (2)	128 (2)
N1B—H1B⋯O21B	0.85 (2)	2.30 (3)	2.683 (2)	108 (2)
O22A—H22A⋯O22Bⁱ	0.97 (2)	1.50 (2)	2.4711 (19)	179 (3)
C4B—H4B⋯O41ⁱⁱ	0.95	2.37	3.240 (2)	152
C5B—H5B⋯O12ⁱⁱⁱ	0.95	2.44	3.339 (2)	158
C8A—H8A⋯O21B	0.95	2.39	3.122 (2)	134
Symmetry codes: (i) x-1, y, z; (ii) x, y, z+1; (iii) -x+1, -y+2, -z+1.

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807062757/sf2012sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807062757/sf2012Isup2.hkl

checkCIF report

Comment top

Picrylsulfonic acid (2,4,6-trinitrobenzenesulfonic acid) reacts with certain Lewis bases to form 1:1 proton-transfer salts and the structures of a small number of these are known: with guanidine (Russell & Ward, 1997) and quinoline (Smith, Wermuth & Healy, 2006). However, the 1:1 reaction with quinoline-2-carboxylic acid in 80% 2-propanol-water resulted in the adduct salt 2-carboxyquinolinium-2,4,6-trinitrobenzenesulfonate-quinolinium- 2-carboxylate (1/1/1) (I) and the structure is reported here. In (I), the asymmetric unit comprises a protonated quinaldic acid cation (A), a picrylsulfonate anion and a zwitterionic quinaldic acid adduct molecule (B) (Fig. 1). The cation and the adduct species form a pseudo-dimer through a twisted cyclic hydrogen-bonded duplex N–H···O association [graph set R²₂(10) (Etter et al., 1990]. This pseudo-dimer incorporates a cyclic R²₂(4) association and two intramolecular S(5) N–H···O_carboxyl associations and is similar to that found in the zwitterionic parent acid (Dobrzyńska & Jerzykiewicz, 2004), the 1:2 L-tartaric acid-quinaldic acid adduct (Smith, Wermuth & White, 2006) and in the analogous (1:1:1) protonated quinaldic acid-zwitterionic adduct compounds with 5-sulfosalicylic acid (Smith et al., 2004) and 4,5-dichlorophthalic acid (Smith, Wermuth & White, 2007). However, in the 1:1 compound with 3,5-dinitrosalicylic acid (Smith, Wermuth, Healy & White, 2007), this dimer is not found.

In (I), the pseudo-dimers are extended into one-dimensional chain structures through short head-to-tail carboxylic acid O–H··· O_carboxyl associations [O···O, 2.4711 (19) Å] (Fig. 2). The picrylsulfonate anions are attached peripherally by single N–H···O_sulfonate hydrogen bonds (Table 1).

All nitro groups of the anion are rotated out of the plane of the benzene ring, particularly those which are ortho to the sulfonate group [torsion angle C1–C2–N2–O22, -139.19 (17) °; C5–C6–N6–O62, 115.70 (17) °], compared to the para- related group [torsion angle C3–C4–N4–O42, 165.79 (16) °].

Related literature top

For other related picrylsulfonate and quinaldic acid structures, see: Russell & Ward (1997); Smith et al. (2004); Smith, Wermuth & Healy (2006); Smith, Wermuth & White (2006); Smith, Wermuth, Healy & White (2007); Smith, Wermuth & White (2007); Dobrzyńska & Jerzykiewicz (2004).

For graph-set nomenclature, see: Etter et al. (1990).

Experimental top

The title compound was synthesized by heating under reflux 1 mmol quantities of 2,4,6-trinitrobenzenesulfonic acid (picrylsulfonic acid) and quinoline-2-carboxylic acid (quinaldic acid) in 50 ml of 80% 2-propanol-water for 10 minutes. After concentration to ca 30 ml, partial room temperature evaporation of the hot-filtered solution gave pale yellow flat prisms of (I) [m.pt. 495–496 K].

Structure description top

For other related picrylsulfonate and quinaldic acid structures, see: Russell & Ward (1997); Smith et al. (2004); Smith, Wermuth & Healy (2006); Smith, Wermuth & White (2006); Smith, Wermuth, Healy & White (2007); Smith, Wermuth & White (2007); Dobrzyńska & Jerzykiewicz (2004).

For graph-set nomenclature, see: Etter et al. (1990).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

	Fig. 1. Molecular configuration and atom naming scheme for the cation, anion and the zwitterionic adduct species in (I). Inter-species hydrogen-bonding interactions are shown as dashed lines. Non-H atom displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A perspective view of the one-dimensional head-to-tail cation-adduct dimer extension and peripheral N–H···O_sulfonate associations in (I). Non-interactive H-atoms are omitted while hydrogen bonds are shown as dashed lines. Symmetry code (iv): x + 1, y, z. For other symmetry codes see Table 1.

2-Carboxyquinolinium–2,4,6-trinitrobenzenesulfonate– quinolinium-2-carboxylate (1/1/1) top

Crystal data top

C₁₀H₈NO₂⁺·C₆H₂N₃O₉S⁻·C₁₀H₇NO₂	Z = 2
M_r = 639.51	F(000) = 656
Triclinic, P1	D_x = 1.667 Mg m⁻³
Hall symbol: -P 1	Melting point = 495–496 K
a = 7.8872 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.4753 (10) Å	Cell parameters from 3558 reflections
c = 14.6617 (12) Å	θ = 2.7–27.5°
α = 66.227 (1)°	µ = 0.21 mm⁻¹
β = 74.997 (2)°	T = 130 K
γ = 82.191 (2)°	Plate, colourless
V = 1274.42 (18) Å³	0.40 × 0.30 × 0.10 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4446 independent reflections
Radiation source: sealed tube	3779 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
φ and ω scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −9→9
T_min = 0.93, T_max = 0.98	k = −14→14
6761 measured reflections	l = −10→17

Refinement top

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)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.090	w = 1/[σ²(F_o²) + (0.0504P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.001
4446 reflections	Δρ_max = 0.26 e Å⁻³
419 parameters	Δρ_min = −0.36 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0035 (9)

Crystal data top

C₁₀H₈NO₂⁺·C₆H₂N₃O₉S⁻·C₁₀H₇NO₂	γ = 82.191 (2)°
M_r = 639.51	V = 1274.42 (18) Å³
Triclinic, P1	Z = 2
a = 7.8872 (6) Å	Mo Kα radiation
b = 12.4753 (10) Å	µ = 0.21 mm⁻¹
c = 14.6617 (12) Å	T = 130 K
α = 66.227 (1)°	0.40 × 0.30 × 0.10 mm
β = 74.997 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4446 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1999)	3779 reflections with I > 2σ(I)
T_min = 0.93, T_max = 0.98	R_int = 0.039
6761 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.26 e Å⁻³
4446 reflections	Δρ_min = −0.36 e Å⁻³
419 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O21A	0.58977 (15)	0.59940 (10)	0.39221 (10)	0.0254 (4)
O21B	1.00107 (15)	0.64175 (10)	0.34714 (10)	0.0241 (4)
O22A	0.38775 (15)	0.50663 (10)	0.36987 (9)	0.0228 (4)
O22B	1.16069 (15)	0.60475 (11)	0.46423 (10)	0.0259 (4)
N1A	0.84672 (18)	0.51549 (12)	0.27485 (11)	0.0189 (4)
N1B	0.74154 (18)	0.73921 (12)	0.45119 (11)	0.0185 (5)
C2A	0.6823 (2)	0.48449 (14)	0.29343 (13)	0.0195 (5)
C2B	0.8899 (2)	0.70550 (14)	0.48319 (13)	0.0180 (5)
C3A	0.6451 (2)	0.41203 (14)	0.24976 (14)	0.0223 (5)
C3B	0.9103 (2)	0.72614 (14)	0.56645 (13)	0.0213 (5)
C4A	0.7771 (2)	0.37568 (15)	0.18609 (14)	0.0236 (6)
C4B	0.7771 (2)	0.78111 (15)	0.61378 (14)	0.0232 (5)
C5A	1.0908 (2)	0.38090 (16)	0.09579 (14)	0.0274 (6)
C5B	0.4742 (2)	0.86973 (15)	0.62801 (14)	0.0246 (6)
C6A	1.2556 (2)	0.41723 (16)	0.07874 (14)	0.0284 (6)
C6B	0.3237 (2)	0.89788 (15)	0.59302 (15)	0.0267 (6)
C7A	1.2868 (2)	0.48655 (16)	0.12761 (14)	0.0265 (6)
C7B	0.3095 (2)	0.87352 (15)	0.50922 (14)	0.0248 (6)
C8A	1.1553 (2)	0.51932 (15)	0.19338 (13)	0.0224 (5)
C8B	0.4452 (2)	0.82010 (14)	0.46165 (14)	0.0217 (5)
C9A	0.9842 (2)	0.48298 (14)	0.21127 (13)	0.0200 (5)
C9B	0.6008 (2)	0.79115 (14)	0.49680 (13)	0.0176 (5)
C10A	0.9496 (2)	0.41196 (14)	0.16341 (14)	0.0217 (6)
C10B	0.6178 (2)	0.81513 (14)	0.58089 (13)	0.0202 (5)
C21A	0.5445 (2)	0.53589 (14)	0.35874 (13)	0.0198 (5)
C21B	1.0288 (2)	0.64568 (14)	0.42510 (14)	0.0206 (5)
S1	0.67941 (6)	0.96877 (4)	0.18966 (3)	0.0221 (1)
O11	0.79371 (16)	1.05360 (11)	0.18376 (10)	0.0275 (4)
O12	0.49579 (16)	0.99398 (11)	0.22231 (9)	0.0270 (4)
O13	0.73845 (16)	0.84886 (11)	0.23828 (9)	0.0288 (4)
O21	0.48489 (16)	0.78413 (11)	0.16864 (10)	0.0287 (4)
O22	0.69059 (17)	0.69083 (10)	0.09636 (10)	0.0296 (4)
O41	0.89200 (16)	0.91344 (11)	−0.26263 (10)	0.0280 (4)
O42	0.90947 (17)	1.10219 (11)	−0.31897 (9)	0.0328 (4)
O61	0.92941 (16)	1.23709 (11)	−0.02903 (10)	0.0295 (4)
O62	0.64569 (16)	1.23611 (11)	0.02533 (10)	0.0295 (4)
N2	0.61840 (19)	0.78074 (13)	0.10551 (11)	0.0222 (5)
N4	0.87752 (18)	1.00599 (13)	−0.25023 (11)	0.0224 (5)
N6	0.78729 (19)	1.19400 (12)	−0.00650 (11)	0.0219 (5)
C1	0.7125 (2)	0.98489 (15)	0.05707 (13)	0.0182 (5)
C2	0.6957 (2)	0.89262 (14)	0.02920 (13)	0.0183 (5)
C3	0.7470 (2)	0.89921 (14)	−0.07008 (13)	0.0189 (5)
C4	0.8198 (2)	1.00040 (15)	−0.14463 (13)	0.0187 (5)
C5	0.8392 (2)	1.09627 (15)	−0.12484 (13)	0.0194 (5)
C6	0.7815 (2)	1.08587 (14)	−0.02403 (13)	0.0189 (5)
H1A	0.863 (3)	0.5625 (18)	0.3025 (16)	0.036 (6)*
H1B	0.737 (3)	0.7269 (19)	0.3989 (18)	0.047 (7)*
H3A	0.52850	0.38810	0.26420	0.0270*
H3B	1.01600	0.70210	0.59000	0.0260*
H4A	0.75210	0.32560	0.15700	0.0280*
H4B	0.79170	0.79670	0.66950	0.0280*
H5A	1.07080	0.33450	0.06200	0.0330*
H5B	0.48240	0.88690	0.68420	0.0300*
H6A	1.34990	0.39550	0.03350	0.0340*
H6B	0.22730	0.93430	0.62530	0.0320*
H7A	1.40250	0.51120	0.11450	0.0320*
H7B	0.20370	0.89460	0.48550	0.0300*
H8A	1.17860	0.56560	0.22640	0.0270*
H8B	0.43400	0.80300	0.40590	0.0260*
H22A	0.298 (3)	0.5460 (19)	0.4062 (18)	0.057 (7)*
H3	0.73240	0.83520	−0.08650	0.0230*
H5	0.88950	1.16590	−0.17750	0.0230*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O21A	0.0235 (7)	0.0263 (7)	0.0307 (8)	−0.0017 (5)	−0.0044 (6)	−0.0160 (6)
O21B	0.0219 (7)	0.0299 (7)	0.0259 (7)	−0.0004 (5)	−0.0044 (6)	−0.0169 (6)
O22A	0.0186 (7)	0.0258 (7)	0.0267 (7)	−0.0008 (5)	−0.0045 (6)	−0.0131 (6)
O22B	0.0215 (7)	0.0315 (7)	0.0275 (7)	0.0055 (5)	−0.0079 (6)	−0.0148 (6)
N1A	0.0204 (8)	0.0189 (7)	0.0192 (8)	−0.0005 (6)	−0.0049 (6)	−0.0090 (7)
N1B	0.0215 (8)	0.0199 (8)	0.0162 (8)	−0.0008 (6)	−0.0036 (6)	−0.0094 (7)
C2A	0.0225 (9)	0.0155 (8)	0.0176 (9)	0.0001 (7)	−0.0066 (8)	−0.0025 (7)
C2B	0.0198 (9)	0.0145 (8)	0.0174 (9)	−0.0026 (7)	−0.0043 (7)	−0.0031 (7)
C3A	0.0227 (9)	0.0185 (9)	0.0246 (10)	−0.0028 (7)	−0.0050 (8)	−0.0068 (8)
C3B	0.0228 (9)	0.0216 (9)	0.0190 (9)	−0.0024 (7)	−0.0062 (8)	−0.0060 (8)
C4A	0.0301 (10)	0.0191 (9)	0.0246 (10)	−0.0015 (8)	−0.0070 (8)	−0.0106 (8)
C4B	0.0306 (10)	0.0237 (9)	0.0180 (9)	−0.0064 (8)	−0.0054 (8)	−0.0092 (8)
C5A	0.0334 (11)	0.0268 (10)	0.0238 (10)	0.0017 (8)	−0.0044 (9)	−0.0136 (9)
C5B	0.0326 (11)	0.0208 (9)	0.0202 (10)	−0.0043 (8)	0.0018 (8)	−0.0113 (8)
C6A	0.0278 (10)	0.0302 (10)	0.0237 (10)	0.0040 (8)	−0.0005 (8)	−0.0116 (9)
C6B	0.0261 (10)	0.0208 (9)	0.0275 (11)	−0.0007 (8)	0.0048 (8)	−0.0103 (8)
C7A	0.0217 (10)	0.0296 (10)	0.0244 (10)	0.0000 (8)	−0.0031 (8)	−0.0080 (9)
C7B	0.0218 (10)	0.0218 (9)	0.0279 (11)	−0.0018 (7)	−0.0016 (8)	−0.0086 (8)
C8A	0.0224 (9)	0.0240 (9)	0.0210 (10)	−0.0007 (8)	−0.0061 (8)	−0.0081 (8)
C8B	0.0234 (9)	0.0210 (9)	0.0206 (10)	−0.0035 (7)	−0.0032 (8)	−0.0081 (8)
C9A	0.0239 (9)	0.0179 (9)	0.0155 (9)	0.0030 (7)	−0.0049 (7)	−0.0046 (7)
C9B	0.0203 (9)	0.0147 (8)	0.0165 (9)	−0.0021 (7)	−0.0003 (7)	−0.0065 (7)
C10A	0.0255 (10)	0.0178 (9)	0.0208 (10)	0.0020 (7)	−0.0065 (8)	−0.0065 (8)
C10B	0.0260 (10)	0.0156 (8)	0.0171 (9)	−0.0050 (7)	−0.0004 (8)	−0.0057 (7)
C21A	0.0225 (9)	0.0160 (8)	0.0190 (9)	−0.0001 (7)	−0.0054 (8)	−0.0046 (8)
C21B	0.0197 (9)	0.0190 (9)	0.0221 (10)	−0.0035 (7)	−0.0031 (8)	−0.0069 (8)
S1	0.0203 (2)	0.0327 (3)	0.0160 (2)	0.0025 (2)	−0.0048 (2)	−0.0128 (2)
O11	0.0244 (7)	0.0413 (8)	0.0250 (7)	−0.0010 (6)	−0.0066 (6)	−0.0205 (6)
O12	0.0215 (7)	0.0408 (8)	0.0223 (7)	0.0018 (6)	−0.0029 (5)	−0.0179 (6)
O13	0.0304 (7)	0.0362 (8)	0.0181 (7)	0.0055 (6)	−0.0078 (6)	−0.0094 (6)
O21	0.0224 (7)	0.0347 (7)	0.0228 (7)	−0.0028 (6)	−0.0002 (6)	−0.0072 (6)
O22	0.0380 (8)	0.0202 (7)	0.0280 (7)	0.0022 (6)	−0.0056 (6)	−0.0087 (6)
O41	0.0296 (7)	0.0351 (8)	0.0272 (7)	−0.0040 (6)	−0.0021 (6)	−0.0217 (6)
O42	0.0425 (8)	0.0357 (8)	0.0172 (7)	−0.0152 (6)	−0.0019 (6)	−0.0057 (6)
O61	0.0277 (7)	0.0296 (7)	0.0372 (8)	−0.0040 (6)	−0.0095 (6)	−0.0166 (6)
O62	0.0289 (7)	0.0296 (7)	0.0350 (8)	0.0063 (6)	−0.0075 (6)	−0.0196 (6)
N2	0.0228 (8)	0.0248 (8)	0.0200 (8)	0.0008 (6)	−0.0081 (7)	−0.0082 (7)
N4	0.0209 (8)	0.0300 (9)	0.0175 (8)	−0.0058 (7)	−0.0023 (6)	−0.0101 (7)
N6	0.0229 (9)	0.0238 (8)	0.0225 (8)	0.0009 (7)	−0.0072 (7)	−0.0116 (7)
C1	0.0151 (8)	0.0244 (9)	0.0168 (9)	0.0037 (7)	−0.0057 (7)	−0.0096 (8)
C2	0.0172 (9)	0.0182 (8)	0.0185 (9)	0.0016 (7)	−0.0056 (7)	−0.0059 (7)
C3	0.0183 (9)	0.0202 (9)	0.0213 (9)	0.0030 (7)	−0.0067 (7)	−0.0110 (8)
C4	0.0169 (9)	0.0249 (9)	0.0160 (9)	0.0012 (7)	−0.0040 (7)	−0.0100 (8)
C5	0.0171 (9)	0.0208 (9)	0.0203 (10)	0.0006 (7)	−0.0053 (7)	−0.0075 (8)
C6	0.0174 (9)	0.0214 (9)	0.0228 (10)	0.0037 (7)	−0.0078 (8)	−0.0129 (8)

Geometric parameters (Å, º) top

S1—C1	1.8232 (18)	C5A—C10A	1.412 (3)
S1—O13	1.4442 (15)	C5A—C6A	1.363 (2)
S1—O11	1.4440 (15)	C5B—C6B	1.361 (2)
S1—O12	1.4367 (14)	C5B—C10B	1.410 (3)
O21A—C21A	1.215 (2)	C6A—C7A	1.404 (3)
O21B—C21B	1.239 (2)	C6B—C7B	1.413 (3)
O22A—C21A	1.288 (2)	C7A—C8A	1.363 (3)
O22B—C21B	1.265 (2)	C7B—C8B	1.368 (3)
O22A—H22A	0.97 (2)	C8A—C9A	1.408 (2)
O21—N2	1.218 (2)	C8B—C9B	1.400 (2)
O22—N2	1.228 (2)	C9A—C10A	1.421 (3)
O41—N4	1.226 (2)	C9B—C10B	1.422 (2)
O42—N4	1.223 (2)	C3A—H3A	0.9500
O61—N6	1.218 (2)	C3B—H3B	0.9500
O62—N6	1.229 (2)	C4A—H4A	0.9500
N1A—C2A	1.332 (2)	C4B—H4B	0.9500
N1A—C9A	1.368 (2)	C5A—H5A	0.9500
N1B—C9B	1.367 (2)	C5B—H5B	0.9500
N1B—C2B	1.326 (2)	C6A—H6A	0.9500
N1A—H1A	0.87 (2)	C6B—H6B	0.9500
N1B—H1B	0.85 (2)	C7A—H7A	0.9500
N2—C2	1.480 (2)	C7B—H7B	0.9500
N4—C4	1.472 (2)	C8A—H8A	0.9500
N6—C6	1.480 (2)	C8B—H8B	0.9500
C2A—C3A	1.396 (3)	C1—C2	1.399 (3)
C2A—C21A	1.509 (3)	C1—C6	1.393 (3)
C2B—C21B	1.513 (3)	C2—C3	1.377 (2)
C2B—C3B	1.396 (2)	C3—C4	1.370 (3)
C3A—C4A	1.368 (3)	C4—C5	1.375 (3)
C3B—C4B	1.366 (3)	C5—C6	1.386 (2)
C4A—C10A	1.407 (2)	C3—H3	0.9500
C4B—C10B	1.413 (2)	C5—H5	0.9500

O12—S1—O13	115.62 (8)	C5B—C10B—C9B	118.43 (15)
O12—S1—C1	105.96 (8)	C4B—C10B—C5B	123.52 (16)
O13—S1—C1	102.31 (8)	O21A—C21A—C2A	118.93 (15)
O11—S1—C1	103.56 (8)	O22A—C21A—C2A	113.06 (15)
O11—S1—O12	114.08 (9)	O21A—C21A—O22A	127.99 (17)
O11—S1—O13	113.42 (8)	O21B—C21B—C2B	117.66 (15)
C21A—O22A—H22A	113.0 (15)	O22B—C21B—C2B	114.26 (16)
C2A—N1A—C9A	123.24 (16)	O21B—C21B—O22B	128.07 (17)
C2B—N1B—C9B	124.03 (15)	C2A—C3A—H3A	120.00
C9A—N1A—H1A	120.2 (16)	C4A—C3A—H3A	120.00
C2A—N1A—H1A	116.5 (16)	C2B—C3B—H3B	120.00
C9B—N1B—H1B	119.9 (17)	C4B—C3B—H3B	120.00
C2B—N1B—H1B	116.0 (17)	C10A—C4A—H4A	120.00
O21—N2—C2	118.58 (16)	C3A—C4A—H4A	120.00
O22—N2—C2	116.42 (14)	C10B—C4B—H4B	120.00
O21—N2—O22	124.89 (16)	C3B—C4B—H4B	120.00
O41—N4—C4	117.43 (15)	C6A—C5A—H5A	120.00
O41—N4—O42	124.80 (15)	C10A—C5A—H5A	120.00
O42—N4—C4	117.77 (16)	C6B—C5B—H5B	120.00
O61—N6—C6	118.03 (15)	C10B—C5B—H5B	120.00
O62—N6—C6	116.65 (15)	C5A—C6A—H6A	120.00
O61—N6—O62	125.23 (16)	C7A—C6A—H6A	120.00
C3A—C2A—C21A	123.84 (15)	C5B—C6B—H6B	120.00
N1A—C2A—C21A	116.27 (16)	C7B—C6B—H6B	120.00
N1A—C2A—C3A	119.84 (16)	C6A—C7A—H7A	119.00
N1B—C2B—C3B	119.65 (16)	C8A—C7A—H7A	119.00
C3B—C2B—C21B	123.91 (15)	C6B—C7B—H7B	119.00
N1B—C2B—C21B	116.44 (15)	C8B—C7B—H7B	119.00
C2A—C3A—C4A	119.76 (16)	C7A—C8A—H8A	121.00
C2B—C3B—C4B	119.51 (16)	C9A—C8A—H8A	121.00
C3A—C4A—C10A	120.41 (17)	C7B—C8B—H8B	121.00
C3B—C4B—C10B	120.86 (17)	C9B—C8B—H8B	121.00
C6A—C5A—C10A	120.34 (18)	S1—C1—C2	123.06 (14)
C6B—C5B—C10B	120.03 (17)	S1—C1—C6	121.54 (14)
C5A—C6A—C7A	120.44 (17)	C2—C1—C6	114.77 (16)
C5B—C6B—C7B	120.70 (17)	N2—C2—C1	121.68 (15)
C6A—C7A—C8A	121.67 (16)	N2—C2—C3	115.28 (16)
C6B—C7B—C8B	121.20 (16)	C1—C2—C3	123.04 (16)
C7A—C8A—C9A	118.51 (17)	C2—C3—C4	118.32 (17)
C7B—C8B—C9B	118.57 (17)	N4—C4—C3	118.03 (17)
C8A—C9A—C10A	120.87 (16)	N4—C4—C5	119.17 (16)
N1A—C9A—C8A	120.92 (16)	C3—C4—C5	122.80 (16)
N1A—C9A—C10A	118.21 (15)	C4—C5—C6	116.46 (16)
N1B—C9B—C8B	121.07 (16)	N6—C6—C1	120.05 (15)
N1B—C9B—C10B	117.84 (15)	N6—C6—C5	115.32 (15)
C8B—C9B—C10B	121.08 (16)	C1—C6—C5	124.54 (17)
C4A—C10A—C5A	123.37 (17)	C2—C3—H3	121.00
C5A—C10A—C9A	118.16 (16)	C4—C3—H3	121.00
C4A—C10A—C9A	118.47 (16)	C4—C5—H5	122.00
C4B—C10B—C9B	118.05 (16)	C6—C5—H5	122.00

O13—S1—C1—C6	−138.21 (15)	C3A—C4A—C10A—C9A	2.5 (3)
O12—S1—C1—C2	−89.31 (16)	C3B—C4B—C10B—C5B	178.54 (18)
O11—S1—C1—C2	150.32 (15)	C3B—C4B—C10B—C9B	−0.4 (3)
O11—S1—C1—C6	−20.10 (17)	C6A—C5A—C10A—C4A	−178.72 (18)
O12—S1—C1—C6	100.27 (15)	C6A—C5A—C10A—C9A	0.9 (3)
O13—S1—C1—C2	32.21 (16)	C10A—C5A—C6A—C7A	−0.4 (3)
C9A—N1A—C2A—C21A	−175.27 (16)	C6B—C5B—C10B—C9B	0.2 (3)
C9A—N1A—C2A—C3A	2.3 (3)	C10B—C5B—C6B—C7B	−0.3 (3)
C2A—N1A—C9A—C10A	−0.5 (3)	C6B—C5B—C10B—C4B	−178.74 (18)
C2A—N1A—C9A—C8A	179.27 (17)	C5A—C6A—C7A—C8A	0.3 (3)
C9B—N1B—C2B—C3B	−2.1 (3)	C5B—C6B—C7B—C8B	0.7 (3)
C2B—N1B—C9B—C10B	2.9 (3)	C6A—C7A—C8A—C9A	−0.6 (3)
C9B—N1B—C2B—C21B	177.93 (16)	C6B—C7B—C8B—C9B	−0.9 (3)
C2B—N1B—C9B—C8B	−177.26 (17)	C7A—C8A—C9A—C10A	1.1 (3)
O21—N2—C2—C3	−134.74 (17)	C7A—C8A—C9A—N1A	−178.59 (17)
O21—N2—C2—C1	44.5 (2)	C7B—C8B—C9B—N1B	−179.04 (17)
O22—N2—C2—C1	−139.19 (17)	C7B—C8B—C9B—C10B	0.8 (3)
O22—N2—C2—C3	41.6 (2)	N1A—C9A—C10A—C4A	−1.9 (3)
O41—N4—C4—C3	−15.1 (2)	C8A—C9A—C10A—C5A	−1.3 (3)
O42—N4—C4—C5	−13.6 (2)	N1A—C9A—C10A—C5A	178.43 (16)
O41—N4—C4—C5	165.55 (16)	C8A—C9A—C10A—C4A	178.37 (17)
O42—N4—C4—C3	165.79 (16)	N1B—C9B—C10B—C4B	−1.6 (3)
O61—N6—C6—C1	122.44 (18)	N1B—C9B—C10B—C5B	179.39 (16)
O62—N6—C6—C1	−61.0 (2)	C8B—C9B—C10B—C4B	178.57 (17)
O62—N6—C6—C5	115.70 (17)	C8B—C9B—C10B—C5B	−0.4 (3)
O61—N6—C6—C5	−60.9 (2)	S1—C1—C2—N2	11.3 (2)
N1A—C2A—C3A—C4A	−1.6 (3)	S1—C1—C2—C3	−169.48 (14)
C21A—C2A—C3A—C4A	175.71 (17)	C6—C1—C2—N2	−177.64 (15)
C3A—C2A—C21A—O22A	−0.4 (2)	C6—C1—C2—C3	1.5 (3)
N1A—C2A—C21A—O21A	−1.6 (2)	S1—C1—C6—N6	−15.7 (2)
N1A—C2A—C21A—O22A	177.05 (15)	S1—C1—C6—C5	167.94 (14)
C3A—C2A—C21A—O21A	−178.99 (17)	C2—C1—C6—N6	173.10 (15)
N1B—C2B—C3B—C4B	−0.2 (3)	C2—C1—C6—C5	−3.2 (3)
C21B—C2B—C3B—C4B	179.87 (17)	N2—C2—C3—C4	−179.94 (15)
N1B—C2B—C21B—O21B	6.2 (2)	C1—C2—C3—C4	0.8 (3)
C3B—C2B—C21B—O22B	6.6 (3)	C2—C3—C4—N4	178.82 (15)
C3B—C2B—C21B—O21B	−173.77 (17)	C2—C3—C4—C5	−1.8 (3)
N1B—C2B—C21B—O22B	−173.36 (16)	N4—C4—C5—C6	179.65 (15)
C2A—C3A—C4A—C10A	−0.8 (3)	C3—C4—C5—C6	0.3 (3)
C2B—C3B—C4B—C10B	1.3 (3)	C4—C5—C6—N6	−174.09 (15)
C3A—C4A—C10A—C5A	−177.87 (18)	C4—C5—C6—C1	2.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O21A	0.87 (2)	2.31 (2)	2.690 (2)	106.3 (18)
N1A—H1A···O21B	0.87 (2)	1.94 (2)	2.761 (2)	155 (2)
N1B—H1B···O13	0.85 (2)	2.23 (2)	2.8643 (19)	132 (2)
N1B—H1B···O21A	0.85 (2)	2.14 (3)	2.746 (2)	128 (2)
N1B—H1B···O21B	0.85 (2)	2.30 (3)	2.683 (2)	108 (2)
O22A—H22A···O22Bⁱ	0.97 (2)	1.50 (2)	2.4711 (19)	179 (3)
C4B—H4B···O41ⁱⁱ	0.95	2.37	3.240 (2)	152
C5B—H5B···O12ⁱⁱⁱ	0.95	2.44	3.339 (2)	158
C8A—H8A···O21B	0.95	2.39	3.122 (2)	134

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

Experimental details

Crystal data
Chemical formula	C₁₀H₈NO₂⁺·C₆H₂N₃O₉S⁻·C₁₀H₇NO₂
M_r	639.51
Crystal system, space group	Triclinic, P1
Temperature (K)	130
a, b, c (Å)	7.8872 (6), 12.4753 (10), 14.6617 (12)
α, β, γ (°)	66.227 (1), 74.997 (2), 82.191 (2)
V (Å³)	1274.42 (18)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.40 × 0.30 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1999)
T_min, T_max	0.93, 0.98
No. of measured, independent and observed [I > 2σ(I)] reflections	6761, 4446, 3779
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.090, 1.00
No. of reflections	4446
No. of parameters	419
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.36

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O21A	0.87 (2)	2.31 (2)	2.690 (2)	106.3 (18)
N1A—H1A···O21B	0.87 (2)	1.94 (2)	2.761 (2)	155 (2)
N1B—H1B···O13	0.85 (2)	2.23 (2)	2.8643 (19)	132 (2)
N1B—H1B···O21A	0.85 (2)	2.14 (3)	2.746 (2)	128 (2)
N1B—H1B···O21B	0.85 (2)	2.30 (3)	2.683 (2)	108 (2)
O22A—H22A···O22Bⁱ	0.97 (2)	1.50 (2)	2.4711 (19)	179 (3)
C4B—H4B···O41ⁱⁱ	0.95	2.37	3.240 (2)	152
C5B—H5B···O12ⁱⁱⁱ	0.95	2.44	3.339 (2)	158
C8A—H8A···O21B	0.95	2.39	3.122 (2)	134

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

Acknowledgements

The authors acknowledge financial support from the School of Physical and Chemical Sciences, Queensland University of Technology, the School of Biomolecular and Physical Sciences, Griffith University, and the School of Chemistry, University of Melbourne.

References

Bruker (1999). SADABS (Version 2.03) and SAINT (Version 6.02). Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2000). SMART. Version 5.55. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dobrzyńska, D. & Jerzykiewicz, L. B. (2004). J. Chem. Crystallogr. 34, 51–55. Web of Science CSD CrossRef CAS Google Scholar
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262. CrossRef CAS Web of Science IUCr Journals Google Scholar
Russell, V. A. & Ward, M. D. (1997). J. Mater. Chem. 7, 1123–1133. CSD CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of Göttingen, Germany. Google Scholar
Smith, G., Wermuth, U. D. & Healy, P. C. (2006). Acta Cryst. E62, o5510–o5512. Web of Science CSD CrossRef IUCr Journals Google Scholar
Smith, G., Wermuth, U. D., Healy, P. C. & White, J. M. (2007). Aust. J. Chem. 60, 264–277. Web of Science CSD CrossRef CAS Google Scholar
Smith, G., Wermuth, U. D. & White, J. M. (2004). Acta Cryst. C60, o575–o581. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Smith, G., Wermuth, U. D. & White, J. M. (2006). Acta Cryst. C62, o694–o698. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Smith, G., Wermuth, U. D. & White, J. M. (2007). Unpublished data. Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-Carb­oxy­quinolinium–2,4,6-tri­nitro­benzene­sulfonate–quinolinium-2-carboxyl­ate (1/1/1)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-Carboxyquinolinium–2,4,6-trinitrobenzenesulfonate–quinolinium-2-carboxylate (1/1/1)