Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
The crystal structure of the 1:1 proton-transfer compound of 8-amino­quinoline with toluene-4-sulfonic acid, viz. quinolin-8-aminium toluene-4-sulfonate, C9H9N2+·C7H7O3S-, is different from previously characterized proton-transfer compounds of 8-amino­quinoline, in that the 8-amino group rather than the quinoline N atom is protonated. All H atoms of this aminium group are subsequently involved in intermolec­ular hydrogen-bonding interactions with sulfonate O-atom acceptors, linking the cationic and anionic species and forming a linear polymer structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804014898/bt6474sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804014898/bt6474Isup2.hkl
Contains datablock I

CCDC reference: 245336

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • R factor = 0.041
  • wR factor = 0.124
  • Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level C ABSMU01_ALERT_1_C The ratio of given/expected absorption coefficient lies outside the range 0.99 <> 1.01 Calculated value of mu = 0.225 Value of mu given = 0.220 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C1 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C4
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 2 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

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: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON for Windows (Spek, 1999); software used to prepare material for publication: PLATON for Windows.

(I) top
Crystal data top
C9H9N2+·C7H7O3SZ = 2
Mr = 316.37F(000) = 332
Triclinic, P1Dx = 1.368 Mg m3
Hall symbol: -P 1Melting point: 421.5–425.0 K K
a = 6.0986 (14) ÅMo Kα radiation, λ = 0.71069 Å
b = 9.8930 (17) ÅCell parameters from 25 reflections
c = 13.424 (2) Åθ = 12.6–17.4°
α = 78.11 (15)°µ = 0.22 mm1
β = 79.217 (16)°T = 298 K
γ = 78.599 (14)°Prism, colourless
V = 767.8 (4) Å30.40 × 0.20 × 0.18 mm
Data collection top
Rigaku AFC-7R
diffractometer
Rint = 0.031
Radiation source: Rigaku rotating anodeθmax = 27.5°, θmin = 2.9°
Graphite monochromatorh = 73
ω–2θ scansk = 1212
4042 measured reflectionsl = 1717
3528 independent reflections3 standard reflections every 150 reflections
2857 reflections with I > 2σ(I) intensity decay: 0.4%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.124 w = 1/[σ2(Fo2) + (0.1P)2 + 2.0104P]
where P = (Fo2 + 2Fc2)/3
S = 0.83(Δ/σ)max < 0.001
3528 reflectionsΔρmax = 0.28 e Å3
212 parametersΔρmin = 0.29 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.019 (3)
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
S10.39220 (8)0.10971 (5)0.79655 (4)0.0376 (1)
O10.1609 (3)0.12739 (17)0.79790 (12)0.0527 (5)
O20.5576 (3)0.23467 (15)0.78809 (13)0.0581 (5)
O30.4115 (2)0.04746 (15)0.88447 (10)0.0435 (4)
C10.4596 (3)0.01601 (19)0.68580 (14)0.0378 (5)
C20.6807 (4)0.0115 (3)0.6377 (2)0.0622 (8)
C30.7329 (5)0.1154 (3)0.5544 (2)0.0723 (9)
C40.5702 (5)0.2217 (3)0.51779 (17)0.0608 (9)
C50.3524 (5)0.2257 (3)0.5683 (2)0.0757 (10)
C60.2961 (4)0.1231 (3)0.6517 (2)0.0627 (8)
C70.6330 (7)0.3319 (4)0.4260 (2)0.0936 (13)
N111.1098 (3)0.81485 (16)0.10916 (13)0.0404 (5)
N810.8164 (3)0.87545 (17)0.03296 (13)0.0384 (5)
C211.2512 (4)0.7857 (2)0.17622 (18)0.0512 (7)
C311.2863 (4)0.6575 (3)0.24472 (19)0.0571 (8)
C411.1705 (4)0.5547 (2)0.24159 (17)0.0513 (7)
C510.8890 (4)0.4787 (2)0.16153 (17)0.0490 (6)
C610.7435 (4)0.5092 (2)0.09254 (19)0.0544 (8)
C710.7168 (4)0.6410 (2)0.02750 (17)0.0473 (6)
C810.8385 (3)0.73882 (18)0.03510 (14)0.0352 (5)
C910.9915 (3)0.71256 (18)0.10641 (13)0.0340 (5)
C1011.0166 (3)0.57887 (19)0.17142 (14)0.0401 (5)
H20.7962000.0630000.66100.0740*
H30.8877000.1129000.52190.0850*
H50.2372000.3011000.54580.0890*
H60.1421000.1257000.68450.0750*
H7A0.7907000.3381000.41960.1120*
H7B0.6074000.3088000.36450.1120*
H7C0.5466000.4212000.43490.1120*
H211.3342000.85660.1797000.0600*
H311.3902000.64290.2929000.0670*
H411.1927000.46620.2867000.0600*
H510.9063000.38830.2045000.0570*
H610.6577000.44030.0875000.0640*
H710.6139000.66150.0221000.0560*
H81A0.683 (4)0.890 (2)0.0639 (17)0.044 (6)*
H81B0.813 (4)0.940 (3)0.004 (2)0.058 (7)*
H81C0.946 (5)0.880 (3)0.087 (2)0.064 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0423 (3)0.0324 (2)0.0378 (2)0.0111 (2)0.0040 (2)0.0029 (2)
O10.0530 (9)0.0577 (9)0.0521 (8)0.0275 (7)0.0065 (7)0.0043 (7)
O20.0669 (10)0.0357 (8)0.0629 (10)0.0022 (7)0.0032 (8)0.0052 (7)
O30.0502 (8)0.0452 (8)0.0364 (7)0.0115 (6)0.0076 (6)0.0055 (6)
C10.0449 (10)0.0370 (9)0.0324 (8)0.0117 (8)0.0034 (7)0.0057 (7)
C20.0520 (13)0.0526 (13)0.0663 (15)0.0034 (10)0.0119 (11)0.0011 (11)
C30.0703 (17)0.0682 (16)0.0636 (16)0.0194 (14)0.0251 (13)0.0027 (13)
C40.0915 (19)0.0584 (14)0.0346 (10)0.0299 (13)0.0042 (11)0.0011 (10)
C50.0765 (18)0.0722 (17)0.0653 (16)0.0113 (14)0.0207 (14)0.0257 (14)
C60.0481 (12)0.0695 (16)0.0574 (14)0.0080 (11)0.0070 (10)0.0161 (12)
C70.151 (3)0.082 (2)0.0469 (14)0.053 (2)0.0025 (17)0.0118 (14)
N110.0455 (9)0.0327 (8)0.0442 (9)0.0115 (7)0.0077 (7)0.0042 (6)
N810.0445 (9)0.0309 (8)0.0407 (8)0.0102 (7)0.0108 (7)0.0007 (6)
C210.0564 (13)0.0436 (11)0.0601 (13)0.0151 (10)0.0185 (10)0.0087 (10)
C310.0632 (14)0.0544 (13)0.0553 (13)0.0028 (11)0.0245 (11)0.0059 (10)
C410.0640 (14)0.0391 (10)0.0451 (11)0.0022 (9)0.0109 (10)0.0019 (9)
C510.0648 (13)0.0313 (9)0.0465 (11)0.0159 (9)0.0028 (10)0.0002 (8)
C610.0633 (14)0.0392 (11)0.0648 (14)0.0274 (10)0.0041 (11)0.0056 (10)
C710.0499 (11)0.0443 (11)0.0517 (11)0.0187 (9)0.0085 (9)0.0066 (9)
C810.0390 (9)0.0291 (8)0.0357 (9)0.0087 (7)0.0003 (7)0.0042 (7)
C910.0373 (9)0.0286 (8)0.0344 (8)0.0072 (7)0.0006 (7)0.0055 (7)
C1010.0482 (10)0.0301 (9)0.0376 (9)0.0061 (7)0.0025 (8)0.0045 (7)
Geometric parameters (Å, º) top
S1—O11.452 (2)C6—H60.9576
S1—O21.4425 (17)C7—H7B0.9478
S1—O31.4719 (15)C7—H7C0.9531
S1—C11.771 (2)C7—H7A0.9625
N11—C911.364 (3)C21—C311.409 (4)
N11—C211.312 (3)C31—C411.359 (4)
N81—C811.464 (2)C41—C1011.405 (3)
N81—H81B0.88 (3)C51—C1011.415 (3)
N81—H81C0.97 (3)C51—C611.350 (3)
N81—H81A0.95 (2)C61—C711.410 (3)
C1—C61.371 (3)C71—C811.360 (3)
C1—C21.378 (3)C81—C911.411 (3)
C2—C31.389 (4)C91—C1011.424 (3)
C3—C41.374 (4)C21—H210.9556
C4—C51.371 (4)C31—H310.9588
C4—C71.513 (4)C41—H410.9575
C5—C61.388 (4)C51—H510.9573
C2—H20.9588C61—H610.9572
C3—H30.9609C71—H710.9636
C5—H50.9594
O1—S1—O2114.4 (3)C4—C7—H7B110.70
O1—S1—O3111.4 (3)C4—C7—H7C110.29
O1—S1—C1106.6 (3)H7A—C7—H7B108.60
O2—S1—O3111.5 (3)H7A—C7—H7C108.13
O2—S1—C1107.0 (3)H7B—C7—H7C109.39
O3—S1—C1105.3 (3)N11—C21—C31124.4 (4)
C21—N11—C91116.8 (3)C21—C31—C41119.0 (4)
H81B—N81—H81C108 (2)C31—C41—C101119.5 (4)
C81—N81—H81C110.6 (18)C61—C51—C101120.8 (4)
C81—N81—H81B108.0 (18)C51—C61—C71120.9 (4)
C81—N81—H81A109.6 (13)C61—C71—C81119.4 (4)
H81A—N81—H81B112 (2)N81—C81—C91117.8 (3)
H81A—N81—H81C109 (2)N81—C81—C71120.3 (3)
S1—C1—C6120.4 (3)C71—C81—C91121.9 (3)
C2—C1—C6119.7 (4)N11—C91—C101123.2 (3)
S1—C1—C2119.7 (3)N11—C91—C81118.9 (3)
C1—C2—C3119.0 (4)C81—C91—C101118.0 (3)
C2—C3—C4122.0 (4)C51—C101—C91119.0 (3)
C3—C4—C5117.9 (4)C41—C101—C51124.0 (4)
C3—C4—C7120.5 (4)C41—C101—C91117.0 (3)
C5—C4—C7121.6 (4)N11—C21—H21117.92
C4—C5—C6121.2 (4)C31—C21—H21117.70
C1—C6—C5120.2 (4)C21—C31—H31120.56
C1—C2—H2120.32C41—C31—H31120.42
C3—C2—H2120.64C31—C41—H41120.67
C4—C3—H3119.24C101—C41—H41119.78
C2—C3—H3118.79C61—C51—H51119.78
C4—C5—H5119.34C101—C51—H51119.37
C6—C5—H5119.51C51—C61—H61119.56
C1—C6—H6119.80C71—C61—H61119.53
C5—C6—H6120.01C61—C71—H71120.36
C4—C7—H7A109.68C81—C71—H71120.27
O1—S1—C1—C2151.2 (4)N11—C21—C31—C411.0 (5)
O1—S1—C1—C633.1 (4)C21—C31—C41—C1010.9 (5)
O2—S1—C1—C228.4 (4)C31—C41—C101—C51179.6 (4)
O2—S1—C1—C6156.0 (4)C31—C41—C101—C910.1 (4)
O3—S1—C1—C290.4 (4)C101—C51—C61—C710.8 (5)
O3—S1—C1—C685.3 (4)C61—C51—C101—C41179.8 (4)
C21—N11—C91—C81179.6 (4)C61—C51—C101—C910.8 (4)
C21—N11—C91—C1010.4 (4)C51—C61—C71—C810.5 (5)
C91—N11—C21—C310.4 (4)C61—C71—C81—C910.0 (4)
C2—C1—C6—C50.8 (5)C61—C71—C81—N81178.9 (4)
C6—C1—C2—C30.7 (5)N81—C81—C91—N110.4 (4)
S1—C1—C6—C5176.4 (4)N81—C81—C91—C101178.9 (3)
S1—C1—C2—C3176.4 (4)C71—C81—C91—N11179.3 (4)
C1—C2—C3—C40.7 (5)C71—C81—C91—C1010.1 (4)
C2—C3—C4—C52.1 (5)N11—C91—C101—C410.6 (4)
C2—C3—C4—C7179.2 (4)C81—C91—C101—C41179.8 (3)
C3—C4—C5—C62.1 (5)N11—C91—C101—C51178.9 (4)
C7—C4—C5—C6179.2 (4)C81—C91—C101—C510.3 (4)
C4—C5—C6—C10.7 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N81—H81A···O3i0.95 (2)1.86 (2)2.800 (2)168.6 (18)
N81—H81B···O3ii0.88 (3)2.14 (3)2.868 (2)140 (2)
N81—H81C···O1iii0.97 (3)1.83 (3)2.791 (3)169 (3)
C21—H21···O3iv0.962.593.494 (3)158
Symmetry codes: (i) x, y+1, z1; (ii) x+1, y+1, z+1; (iii) x+1, y+1, z1; (iv) x+2, y+1, z+1.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds