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The title compound, C9H8N+·C6H2N3O9S, forms a simple dimer structure through a single N+—H...O hydrogen bond involving a sulfonate O atom of the cation. Some cation–cation π–π inter­actions are also present.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806046447/fl2075sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806046447/fl2075Isup2.hkl
Contains datablock I

CCDC reference: 629674

Key indicators

  • Single-crystal X-ray study
  • T = 297 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.038
  • wR factor = 0.111
  • Data-to-parameter ratio = 11.4

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT430_ALERT_2_B Short Inter D...A Contact O1A .. N4 .. 2.84 Ang.
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1999); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

quinolinium 2,4,6-trinitrobenzenesulfonate' top
Crystal data top
C9H8N+·C6H2N3O9SZ = 2
Mr = 422.33F(000) = 432
Triclinic, P1Dx = 1.632 Mg m3
Hall symbol: -P 1Melting point = 532.7–533.9 K
a = 8.1070 (19) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.486 (2) ÅCell parameters from 25 reflections
c = 12.581 (2) Åθ = 12.6–16.5°
α = 79.41 (2)°µ = 0.25 mm1
β = 82.347 (16)°T = 297 K
γ = 64.909 (16)°Plate, yellow
V = 859.6 (3) Å30.36 × 0.28 × 0.11 mm
Data collection top
Rigaku AFC 7R
diffractometer
1992 reflections with I > 2σ(I)
Radiation source: Rigaku rotating anodeRint = 0.017
Graphite monochromatorθmax = 25.0°, θmin = 2.7°
ω/2θ scansh = 94
Absorption correction: ψ scan
TEXSAN for Windows (Molecular Structure Corporation, 1999)
k = 1110
Tmin = 0.90, Tmax = 0.97l = 1414
3552 measured reflections3 standard reflections every 150 min
3026 independent reflections intensity decay: 0.5%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111H atoms treated by a mixture of independent and constrained refinement
S = 0.95 w = 1/[σ2(Fo2) + (0.0556P)2 + 0.1982P]
where P = (Fo2 + 2Fc2)/3
3026 reflections(Δ/σ)max < 0.001
266 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.30 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'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
xyzUiso*/Ueq
S10.35708 (9)0.02704 (8)0.26483 (5)0.0377 (2)
O1A0.3729 (3)0.1677 (2)0.22990 (16)0.0511 (7)
O1B0.4835 (3)0.0555 (2)0.34674 (14)0.0471 (6)
O1C0.1769 (3)0.0836 (2)0.29089 (15)0.0506 (7)
O2A0.0898 (3)0.1261 (3)0.06730 (18)0.0636 (9)
O2B0.0133 (3)0.3612 (3)0.1047 (2)0.0743 (9)
O4A0.4999 (3)0.4874 (2)0.13872 (17)0.0611 (8)
O4B0.7793 (3)0.3423 (3)0.09948 (18)0.0721 (10)
O6A0.8474 (3)0.0350 (3)0.2528 (2)0.0782 (10)
O6B0.7853 (3)0.2054 (2)0.19261 (18)0.0612 (8)
N20.1242 (3)0.2319 (3)0.08595 (18)0.0456 (8)
N40.6169 (4)0.3738 (3)0.08905 (18)0.0483 (9)
N60.7609 (3)0.0713 (3)0.19921 (19)0.0462 (8)
C10.4378 (3)0.0794 (3)0.15064 (19)0.0313 (8)
C20.3192 (3)0.2018 (3)0.08054 (19)0.0335 (8)
C30.3726 (4)0.2980 (3)0.0019 (2)0.0376 (8)
C40.5553 (3)0.2696 (3)0.00793 (19)0.0354 (8)
C50.6808 (3)0.1511 (3)0.0568 (2)0.0371 (8)
C60.6195 (3)0.0582 (3)0.1339 (2)0.0343 (8)
N110.3204 (3)0.3278 (3)0.5264 (2)0.0474 (8)
C210.2806 (5)0.2900 (4)0.4405 (3)0.0580 (11)
C310.1955 (5)0.4045 (4)0.3568 (3)0.0612 (11)
C410.1542 (4)0.5576 (4)0.3633 (2)0.0558 (10)
C510.1546 (4)0.7558 (3)0.4672 (2)0.0508 (10)
C610.1938 (4)0.7874 (3)0.5588 (3)0.0592 (11)
C710.2766 (5)0.6662 (4)0.6431 (3)0.0607 (11)
C810.3210 (4)0.5132 (3)0.6337 (2)0.0512 (10)
C910.2802 (4)0.4792 (3)0.5395 (2)0.0399 (8)
C1010.1953 (4)0.5993 (3)0.4544 (2)0.0422 (9)
H30.2874000.3807000.0437000.0450*
H50.8059000.1336000.0487000.0450*
H110.381 (4)0.253 (3)0.578 (2)0.052 (9)*
H210.3109000.1828000.4361000.0690*
H310.1659000.3768000.2953000.0740*
H410.0970000.6368000.3054000.0670*
H510.0995000.8392000.4111000.0610*
H610.1649000.8932000.5665000.0710*
H710.3019000.6913000.7071000.0730*
H810.3785000.4313000.6901000.0610*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0416 (4)0.0365 (4)0.0329 (3)0.0169 (3)0.0012 (3)0.0014 (3)
O1A0.0654 (13)0.0425 (11)0.0516 (12)0.0294 (10)0.0019 (10)0.0072 (9)
O1B0.0563 (12)0.0483 (11)0.0322 (10)0.0192 (9)0.0122 (9)0.0061 (8)
O1C0.0409 (11)0.0497 (12)0.0491 (12)0.0132 (9)0.0087 (9)0.0002 (9)
O2A0.0447 (13)0.0869 (17)0.0737 (15)0.0396 (12)0.0103 (11)0.0095 (13)
O2B0.0369 (13)0.0606 (15)0.0977 (19)0.0012 (11)0.0060 (12)0.0031 (13)
O4A0.0881 (17)0.0494 (12)0.0488 (12)0.0363 (12)0.0146 (12)0.0139 (10)
O4B0.0659 (15)0.111 (2)0.0574 (14)0.0636 (15)0.0070 (11)0.0158 (13)
O6A0.0712 (16)0.0808 (17)0.0902 (18)0.0354 (13)0.0550 (14)0.0165 (14)
O6B0.0529 (13)0.0416 (12)0.0731 (15)0.0050 (10)0.0146 (11)0.0021 (11)
N20.0320 (13)0.0555 (15)0.0442 (14)0.0170 (12)0.0104 (10)0.0086 (11)
N40.0626 (18)0.0609 (16)0.0362 (13)0.0414 (14)0.0047 (12)0.0010 (12)
N60.0322 (13)0.0533 (16)0.0480 (14)0.0143 (11)0.0156 (11)0.0061 (11)
C10.0327 (14)0.0336 (13)0.0291 (12)0.0154 (11)0.0058 (10)0.0005 (10)
C20.0271 (13)0.0392 (14)0.0347 (13)0.0137 (11)0.0066 (10)0.0028 (11)
C30.0407 (15)0.0380 (14)0.0329 (13)0.0156 (12)0.0119 (11)0.0032 (11)
C40.0434 (15)0.0403 (14)0.0309 (13)0.0268 (12)0.0057 (11)0.0013 (11)
C50.0293 (14)0.0469 (15)0.0392 (14)0.0199 (12)0.0052 (11)0.0029 (12)
C60.0320 (13)0.0356 (14)0.0332 (13)0.0115 (11)0.0107 (10)0.0008 (11)
N110.0497 (15)0.0386 (13)0.0438 (14)0.0112 (11)0.0084 (12)0.0051 (11)
C210.062 (2)0.0531 (19)0.058 (2)0.0206 (16)0.0061 (16)0.0113 (15)
C310.063 (2)0.069 (2)0.0476 (18)0.0195 (18)0.0123 (16)0.0115 (16)
C410.0484 (18)0.065 (2)0.0358 (16)0.0095 (15)0.0098 (13)0.0069 (14)
C510.0451 (17)0.0398 (16)0.0503 (18)0.0078 (13)0.0007 (14)0.0080 (13)
C610.062 (2)0.0377 (16)0.069 (2)0.0153 (15)0.0031 (17)0.0040 (15)
C710.068 (2)0.058 (2)0.0527 (19)0.0198 (17)0.0102 (16)0.0104 (15)
C810.0537 (18)0.0483 (17)0.0412 (16)0.0134 (14)0.0123 (14)0.0065 (13)
C910.0346 (14)0.0385 (15)0.0392 (14)0.0111 (12)0.0024 (11)0.0023 (11)
C1010.0344 (15)0.0416 (15)0.0365 (15)0.0077 (12)0.0019 (11)0.0053 (12)
Geometric parameters (Å, º) top
S1—O1A1.430 (2)C4—C51.370 (4)
S1—O1B1.459 (2)C5—C61.376 (4)
S1—O1C1.429 (2)C3—H30.9500
S1—C11.813 (3)C5—H50.9500
O2A—N21.217 (4)C21—C311.379 (5)
O2B—N21.218 (4)C31—C411.361 (5)
O4A—N41.223 (3)C41—C1011.400 (4)
O4B—N41.214 (4)C51—C1011.413 (4)
O6A—N61.217 (4)C51—C611.351 (4)
O6B—N61.219 (3)C61—C711.409 (5)
N2—C21.477 (4)C71—C811.363 (4)
N4—C41.477 (4)C81—C911.398 (4)
N6—C61.478 (4)C91—C1011.415 (4)
N11—C211.317 (5)C21—H210.9500
N11—C911.368 (4)C31—H310.9500
N11—H110.89 (3)C41—H410.9500
C1—C21.398 (4)C51—H510.9500
C1—C61.392 (4)C61—H610.9500
C2—C31.374 (4)C71—H710.9500
C3—C41.381 (4)C81—H810.9500
O1A—S1—O1B113.41 (12)C2—C3—H3121.00
O1A—S1—O1C116.83 (15)C4—C3—H3121.00
O1A—S1—C1106.57 (12)C4—C5—H5121.00
O1B—S1—O1C112.34 (12)C6—C5—H5121.00
O1B—S1—C1102.27 (13)N11—C21—C31120.6 (3)
O1C—S1—C1103.61 (12)C21—C31—C41119.3 (3)
O2A—N2—O2B126.2 (3)C31—C41—C101120.6 (3)
O2A—N2—C2116.4 (3)C61—C51—C101120.3 (2)
O2B—N2—C2117.4 (3)C51—C61—C71121.2 (3)
O4A—N4—O4B125.0 (3)C61—C71—C81120.6 (3)
O4A—N4—C4117.4 (3)C71—C81—C91118.7 (3)
O4B—N4—C4117.6 (2)N11—C91—C101117.4 (2)
O6A—N6—O6B125.3 (3)C81—C91—C101121.6 (2)
O6A—N6—C6117.0 (2)N11—C91—C81121.0 (2)
O6B—N6—C6117.6 (2)C51—C101—C91117.6 (2)
C21—N11—C91123.4 (3)C41—C101—C51123.7 (3)
C21—N11—H11120.0 (18)C41—C101—C91118.7 (3)
C91—N11—H11116.6 (18)N11—C21—H21120.00
S1—C1—C2122.4 (2)C31—C21—H21120.00
C2—C1—C6114.8 (2)C21—C31—H31120.00
S1—C1—C6122.40 (19)C41—C31—H31120.00
C1—C2—C3124.0 (3)C31—C41—H41120.00
N2—C2—C1120.3 (2)C101—C41—H41120.00
N2—C2—C3115.7 (2)C61—C51—H51120.00
C2—C3—C4117.2 (2)C101—C51—H51120.00
N4—C4—C3118.8 (2)C51—C61—H61119.00
N4—C4—C5118.7 (3)C71—C61—H61119.00
C3—C4—C5122.5 (2)C61—C71—H71120.00
C4—C5—C6117.7 (3)C81—C71—H71120.00
C1—C6—C5123.8 (2)C71—C81—H81121.00
N6—C6—C1120.5 (2)C91—C81—H81121.00
N6—C6—C5115.7 (2)
O1A—S1—C1—C297.4 (2)C6—C1—C2—C31.3 (4)
O1A—S1—C1—C690.4 (2)S1—C1—C2—C3171.4 (2)
O1B—S1—C1—C2143.3 (2)C6—C1—C2—N2177.0 (2)
O1B—S1—C1—C628.8 (2)N2—C2—C3—C4177.8 (2)
O1C—S1—C1—C226.4 (2)C1—C2—C3—C40.5 (4)
O1C—S1—C1—C6145.7 (2)C2—C3—C4—C50.1 (4)
O2A—N2—C2—C161.6 (3)C2—C3—C4—N4178.0 (2)
O2A—N2—C2—C3116.8 (3)N4—C4—C5—C6178.2 (2)
O2B—N2—C2—C1120.9 (3)C3—C4—C5—C60.1 (4)
O2B—N2—C2—C360.7 (3)C4—C5—C6—N6178.0 (2)
O4A—N4—C4—C34.9 (4)C4—C5—C6—C11.0 (4)
O4A—N4—C4—C5173.3 (2)N11—C21—C31—C410.6 (6)
O4B—N4—C4—C3176.8 (3)C21—C31—C41—C1010.8 (6)
O4B—N4—C4—C55.0 (4)C31—C41—C101—C910.1 (5)
O6A—N6—C6—C1120.6 (3)C31—C41—C101—C51179.3 (4)
O6A—N6—C6—C560.4 (3)C61—C51—C101—C911.0 (5)
O6B—N6—C6—C161.6 (3)C101—C51—C61—C710.4 (5)
O6B—N6—C6—C5117.4 (3)C61—C51—C101—C41178.1 (3)
C21—N11—C91—C1011.5 (5)C51—C61—C71—C810.7 (6)
C91—N11—C21—C310.6 (6)C61—C71—C81—C911.0 (6)
C21—N11—C91—C81178.2 (3)C71—C81—C91—N11179.4 (3)
S1—C1—C2—N210.4 (3)C71—C81—C91—C1010.3 (5)
S1—C1—C6—N69.9 (3)N11—C91—C101—C411.2 (5)
S1—C1—C6—C5171.1 (2)C81—C91—C101—C41178.5 (3)
C2—C1—C6—N6177.4 (2)N11—C91—C101—C51179.6 (3)
C2—C1—C6—C51.6 (4)C81—C91—C101—C510.7 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11···O1Bi0.89 (3)1.87 (3)2.725 (3)162 (2)
C5—H5···O2Aii0.952.313.241 (4)165
C21—H21···O1B0.952.483.342 (4)150
C81—H81···O1Ai0.952.583.466 (3)155
Symmetry codes: (i) x+1, y, z+1; (ii) x+1, y, z.
 

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