Anhydrous quinolinium 2,4,6-trinitrobenzene­sulfonate

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.

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

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Computing details

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'

Crystal data

C9H8N^+·C6H2N3O9S^−	Z = 2
Mr = 422.33	F(000) = 432
Triclinic, P1	Dx = 1.632 Mg m^−3
Hall symbol: -P 1	Melting point = 532.7–533.9 K
a = 8.1070 (19) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.486 (2) Å	Cell parameters from 25 reflections
c = 12.581 (2) Å	θ = 12.6–16.5°
α = 79.41 (2)°	µ = 0.25 mm^−1
β = 82.347 (16)°	T = 297 K
γ = 64.909 (16)°	Plate, yellow
V = 859.6 (3) Å^3	0.36 × 0.28 × 0.11 mm

Data collection

Rigaku AFC 7R diffractometer	1992 reflections with I > 2σ(I)
Radiation source: Rigaku rotating anode	Rint = 0.017
Graphite monochromator	θmax = 25.0°, θmin = 2.7°
ω/2θ scans	h = −9→4
Absorption correction: ψ scan TEXSAN for Windows (Molecular Structure Corporation, 1999)	k = −11→10
Tmin = 0.90, Tmax = 0.97	l = −14→14
3552 measured reflections	3 standard reflections every 150 min
3026 independent reflections	intensity decay: 0.5%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	w = 1/[σ^2(Fo^2) + (0.0556P)^2 + 0.1982P] where P = (Fo^2 + 2Fc^2)/3
3026 reflections	(Δ/σ)max < 0.001
266 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.30 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.35708 (9)	−0.02704 (8)	0.26483 (5)	0.0377 (2)
O1A	0.3729 (3)	−0.1677 (2)	0.22990 (16)	0.0511 (7)
O1B	0.4835 (3)	−0.0555 (2)	0.34674 (14)	0.0471 (6)
O1C	0.1769 (3)	0.0836 (2)	0.29089 (15)	0.0506 (7)
O2A	0.0898 (3)	0.1261 (3)	0.06730 (18)	0.0636 (9)
O2B	0.0133 (3)	0.3612 (3)	0.1047 (2)	0.0743 (9)
O4A	0.4999 (3)	0.4874 (2)	−0.13872 (17)	0.0611 (8)
O4B	0.7793 (3)	0.3423 (3)	−0.09948 (18)	0.0721 (10)
O6A	0.8474 (3)	−0.0350 (3)	0.2528 (2)	0.0782 (10)
O6B	0.7853 (3)	−0.2054 (2)	0.19261 (18)	0.0612 (8)
N2	0.1242 (3)	0.2319 (3)	0.08595 (18)	0.0456 (8)
N4	0.6169 (4)	0.3738 (3)	−0.08905 (18)	0.0483 (9)
N6	0.7609 (3)	−0.0713 (3)	0.19921 (19)	0.0462 (8)
C1	0.4378 (3)	0.0794 (3)	0.15064 (19)	0.0313 (8)
C2	0.3192 (3)	0.2018 (3)	0.08054 (19)	0.0335 (8)
C3	0.3726 (4)	0.2980 (3)	0.0019 (2)	0.0376 (8)
C4	0.5553 (3)	0.2696 (3)	−0.00793 (19)	0.0354 (8)
C5	0.6808 (3)	0.1511 (3)	0.0568 (2)	0.0371 (8)
C6	0.6195 (3)	0.0582 (3)	0.1339 (2)	0.0343 (8)
N11	0.3204 (3)	0.3278 (3)	0.5264 (2)	0.0474 (8)
C21	0.2806 (5)	0.2900 (4)	0.4405 (3)	0.0580 (11)
C31	0.1955 (5)	0.4045 (4)	0.3568 (3)	0.0612 (11)
C41	0.1542 (4)	0.5576 (4)	0.3633 (2)	0.0558 (10)
C51	0.1546 (4)	0.7558 (3)	0.4672 (2)	0.0508 (10)
C61	0.1938 (4)	0.7874 (3)	0.5588 (3)	0.0592 (11)
C71	0.2766 (5)	0.6662 (4)	0.6431 (3)	0.0607 (11)
C81	0.3210 (4)	0.5132 (3)	0.6337 (2)	0.0512 (10)
C91	0.2802 (4)	0.4792 (3)	0.5395 (2)	0.0399 (8)
C101	0.1953 (4)	0.5993 (3)	0.4544 (2)	0.0422 (9)
H3	0.287400	0.380700	−0.043700	0.0450*
H5	0.805900	0.133600	0.048700	0.0450*
H11	0.381 (4)	0.253 (3)	0.578 (2)	0.052 (9)*
H21	0.310900	0.182800	0.436100	0.0690*
H31	0.165900	0.376800	0.295300	0.0740*
H41	0.097000	0.636800	0.305400	0.0670*
H51	0.099500	0.839200	0.411100	0.0610*
H61	0.164900	0.893200	0.566500	0.0710*
H71	0.301900	0.691300	0.707100	0.0730*
H81	0.378500	0.431300	0.690100	0.0610*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0416 (4)	0.0365 (4)	0.0329 (3)	−0.0169 (3)	−0.0012 (3)	0.0014 (3)
O1A	0.0654 (13)	0.0425 (11)	0.0516 (12)	−0.0294 (10)	0.0019 (10)	−0.0072 (9)
O1B	0.0563 (12)	0.0483 (11)	0.0322 (10)	−0.0192 (9)	−0.0122 (9)	0.0061 (8)
O1C	0.0409 (11)	0.0497 (12)	0.0491 (12)	−0.0132 (9)	0.0087 (9)	0.0002 (9)
O2A	0.0447 (13)	0.0869 (17)	0.0737 (15)	−0.0396 (12)	−0.0103 (11)	−0.0095 (13)
O2B	0.0369 (13)	0.0606 (15)	0.0977 (19)	0.0012 (11)	−0.0060 (12)	0.0031 (13)
O4A	0.0881 (17)	0.0494 (12)	0.0488 (12)	−0.0363 (12)	−0.0146 (12)	0.0139 (10)
O4B	0.0659 (15)	0.111 (2)	0.0574 (14)	−0.0636 (15)	−0.0070 (11)	0.0158 (13)
O6A	0.0712 (16)	0.0808 (17)	0.0902 (18)	−0.0354 (13)	−0.0550 (14)	0.0165 (14)
O6B	0.0529 (13)	0.0416 (12)	0.0731 (15)	−0.0050 (10)	−0.0146 (11)	0.0021 (11)
N2	0.0320 (13)	0.0555 (15)	0.0442 (14)	−0.0170 (12)	−0.0104 (10)	0.0086 (11)
N4	0.0626 (18)	0.0609 (16)	0.0362 (13)	−0.0414 (14)	−0.0047 (12)	−0.0010 (12)
N6	0.0322 (13)	0.0533 (16)	0.0480 (14)	−0.0143 (11)	−0.0156 (11)	0.0061 (11)
C1	0.0327 (14)	0.0336 (13)	0.0291 (12)	−0.0154 (11)	−0.0058 (10)	−0.0005 (10)
C2	0.0271 (13)	0.0392 (14)	0.0347 (13)	−0.0137 (11)	−0.0066 (10)	−0.0028 (11)
C3	0.0407 (15)	0.0380 (14)	0.0329 (13)	−0.0156 (12)	−0.0119 (11)	0.0032 (11)
C4	0.0434 (15)	0.0403 (14)	0.0309 (13)	−0.0268 (12)	−0.0057 (11)	0.0013 (11)
C5	0.0293 (14)	0.0469 (15)	0.0392 (14)	−0.0199 (12)	−0.0052 (11)	−0.0029 (12)
C6	0.0320 (13)	0.0356 (14)	0.0332 (13)	−0.0115 (11)	−0.0107 (10)	0.0008 (11)
N11	0.0497 (15)	0.0386 (13)	0.0438 (14)	−0.0112 (11)	−0.0084 (12)	0.0051 (11)
C21	0.062 (2)	0.0531 (19)	0.058 (2)	−0.0206 (16)	−0.0061 (16)	−0.0113 (15)
C31	0.063 (2)	0.069 (2)	0.0476 (18)	−0.0195 (18)	−0.0123 (16)	−0.0115 (16)
C41	0.0484 (18)	0.065 (2)	0.0358 (16)	−0.0095 (15)	−0.0098 (13)	0.0069 (14)
C51	0.0451 (17)	0.0398 (16)	0.0503 (18)	−0.0078 (13)	0.0007 (14)	0.0080 (13)
C61	0.062 (2)	0.0377 (16)	0.069 (2)	−0.0153 (15)	0.0031 (17)	−0.0040 (15)
C71	0.068 (2)	0.058 (2)	0.0527 (19)	−0.0198 (17)	−0.0102 (16)	−0.0104 (15)
C81	0.0537 (18)	0.0483 (17)	0.0412 (16)	−0.0134 (14)	−0.0123 (14)	0.0065 (13)
C91	0.0346 (14)	0.0385 (15)	0.0392 (14)	−0.0111 (12)	−0.0024 (11)	0.0023 (11)
C101	0.0344 (15)	0.0416 (15)	0.0365 (15)	−0.0077 (12)	0.0019 (11)	0.0053 (12)

Geometric parameters (Å, º)

S1—O1A	1.430 (2)	C4—C5	1.370 (4)
S1—O1B	1.459 (2)	C5—C6	1.376 (4)
S1—O1C	1.429 (2)	C3—H3	0.9500
S1—C1	1.813 (3)	C5—H5	0.9500
O2A—N2	1.217 (4)	C21—C31	1.379 (5)
O2B—N2	1.218 (4)	C31—C41	1.361 (5)
O4A—N4	1.223 (3)	C41—C101	1.400 (4)
O4B—N4	1.214 (4)	C51—C101	1.413 (4)
O6A—N6	1.217 (4)	C51—C61	1.351 (4)
O6B—N6	1.219 (3)	C61—C71	1.409 (5)
N2—C2	1.477 (4)	C71—C81	1.363 (4)
N4—C4	1.477 (4)	C81—C91	1.398 (4)
N6—C6	1.478 (4)	C91—C101	1.415 (4)
N11—C21	1.317 (5)	C21—H21	0.9500
N11—C91	1.368 (4)	C31—H31	0.9500
N11—H11	0.89 (3)	C41—H41	0.9500
C1—C2	1.398 (4)	C51—H51	0.9500
C1—C6	1.392 (4)	C61—H61	0.9500
C2—C3	1.374 (4)	C71—H71	0.9500
C3—C4	1.381 (4)	C81—H81	0.9500
O1A—S1—O1B	113.41 (12)	C2—C3—H3	121.00
O1A—S1—O1C	116.83 (15)	C4—C3—H3	121.00
O1A—S1—C1	106.57 (12)	C4—C5—H5	121.00
O1B—S1—O1C	112.34 (12)	C6—C5—H5	121.00
O1B—S1—C1	102.27 (13)	N11—C21—C31	120.6 (3)
O1C—S1—C1	103.61 (12)	C21—C31—C41	119.3 (3)
O2A—N2—O2B	126.2 (3)	C31—C41—C101	120.6 (3)
O2A—N2—C2	116.4 (3)	C61—C51—C101	120.3 (2)
O2B—N2—C2	117.4 (3)	C51—C61—C71	121.2 (3)
O4A—N4—O4B	125.0 (3)	C61—C71—C81	120.6 (3)
O4A—N4—C4	117.4 (3)	C71—C81—C91	118.7 (3)
O4B—N4—C4	117.6 (2)	N11—C91—C101	117.4 (2)
O6A—N6—O6B	125.3 (3)	C81—C91—C101	121.6 (2)
O6A—N6—C6	117.0 (2)	N11—C91—C81	121.0 (2)
O6B—N6—C6	117.6 (2)	C51—C101—C91	117.6 (2)
C21—N11—C91	123.4 (3)	C41—C101—C51	123.7 (3)
C21—N11—H11	120.0 (18)	C41—C101—C91	118.7 (3)
C91—N11—H11	116.6 (18)	N11—C21—H21	120.00
S1—C1—C2	122.4 (2)	C31—C21—H21	120.00
C2—C1—C6	114.8 (2)	C21—C31—H31	120.00
S1—C1—C6	122.40 (19)	C41—C31—H31	120.00
C1—C2—C3	124.0 (3)	C31—C41—H41	120.00
N2—C2—C1	120.3 (2)	C101—C41—H41	120.00
N2—C2—C3	115.7 (2)	C61—C51—H51	120.00
C2—C3—C4	117.2 (2)	C101—C51—H51	120.00
N4—C4—C3	118.8 (2)	C51—C61—H61	119.00
N4—C4—C5	118.7 (3)	C71—C61—H61	119.00
C3—C4—C5	122.5 (2)	C61—C71—H71	120.00
C4—C5—C6	117.7 (3)	C81—C71—H71	120.00
C1—C6—C5	123.8 (2)	C71—C81—H81	121.00
N6—C6—C1	120.5 (2)	C91—C81—H81	121.00
N6—C6—C5	115.7 (2)
O1A—S1—C1—C2	97.4 (2)	C6—C1—C2—C3	−1.3 (4)
O1A—S1—C1—C6	−90.4 (2)	S1—C1—C2—C3	171.4 (2)
O1B—S1—C1—C2	−143.3 (2)	C6—C1—C2—N2	177.0 (2)
O1B—S1—C1—C6	28.8 (2)	N2—C2—C3—C4	−177.8 (2)
O1C—S1—C1—C2	−26.4 (2)	C1—C2—C3—C4	0.5 (4)
O1C—S1—C1—C6	145.7 (2)	C2—C3—C4—C5	0.1 (4)
O2A—N2—C2—C1	−61.6 (3)	C2—C3—C4—N4	−178.0 (2)
O2A—N2—C2—C3	116.8 (3)	N4—C4—C5—C6	178.2 (2)
O2B—N2—C2—C1	120.9 (3)	C3—C4—C5—C6	0.1 (4)
O2B—N2—C2—C3	−60.7 (3)	C4—C5—C6—N6	178.0 (2)
O4A—N4—C4—C3	4.9 (4)	C4—C5—C6—C1	−1.0 (4)
O4A—N4—C4—C5	−173.3 (2)	N11—C21—C31—C41	0.6 (6)
O4B—N4—C4—C3	−176.8 (3)	C21—C31—C41—C101	−0.8 (6)
O4B—N4—C4—C5	5.0 (4)	C31—C41—C101—C91	−0.1 (5)
O6A—N6—C6—C1	−120.6 (3)	C31—C41—C101—C51	−179.3 (4)
O6A—N6—C6—C5	60.4 (3)	C61—C51—C101—C91	−1.0 (5)
O6B—N6—C6—C1	61.6 (3)	C101—C51—C61—C71	0.4 (5)
O6B—N6—C6—C5	−117.4 (3)	C61—C51—C101—C41	178.1 (3)
C21—N11—C91—C101	−1.5 (5)	C51—C61—C71—C81	0.7 (6)
C91—N11—C21—C31	0.6 (6)	C61—C71—C81—C91	−1.0 (6)
C21—N11—C91—C81	178.2 (3)	C71—C81—C91—N11	−179.4 (3)
S1—C1—C2—N2	−10.4 (3)	C71—C81—C91—C101	0.3 (5)
S1—C1—C6—N6	9.9 (3)	N11—C91—C101—C41	1.2 (5)
S1—C1—C6—C5	−171.1 (2)	C81—C91—C101—C41	−178.5 (3)
C2—C1—C6—N6	−177.4 (2)	N11—C91—C101—C51	−179.6 (3)
C2—C1—C6—C5	1.6 (4)	C81—C91—C101—C51	0.7 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11···O1B^i	0.89 (3)	1.87 (3)	2.725 (3)	162 (2)
C5—H5···O2A^ii	0.95	2.31	3.241 (4)	165
C21—H21···O1B	0.95	2.48	3.342 (4)	150
C81—H81···O1A^i	0.95	2.58	3.466 (3)	155

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