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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
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
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.
Crystal data top
C9H9N2+·C7H7O3S− | Z = 2 |
Mr = 316.37 | F(000) = 332 |
Triclinic, P1 | Dx = 1.368 Mg m−3 |
Hall symbol: -P 1 | Melting point: 421.5–425.0 K K |
a = 6.0986 (14) Å | Mo Kα radiation, λ = 0.71069 Å |
b = 9.8930 (17) Å | Cell parameters from 25 reflections |
c = 13.424 (2) Å | θ = 12.6–17.4° |
α = 78.11 (15)° | µ = 0.22 mm−1 |
β = 79.217 (16)° | T = 298 K |
γ = 78.599 (14)° | Prism, colourless |
V = 767.8 (4) Å3 | 0.40 × 0.20 × 0.18 mm |
Data collection top
Rigaku AFC-7R diffractometer | Rint = 0.031 |
Radiation source: Rigaku rotating anode | θmax = 27.5°, θmin = 2.9° |
Graphite monochromator | h = −7→3 |
ω–2θ scans | k = −12→12 |
4042 measured reflections | l = −17→17 |
3528 independent reflections | 3 standard reflections every 150 reflections |
2857 reflections with I > 2σ(I) | intensity decay: 0.4% |
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)] = 0.042 | H 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 reflections | Δρmax = 0.28 e Å−3 |
212 parameters | Δρmin = −0.29 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
S1 | 0.39220 (8) | −0.10971 (5) | 0.79655 (4) | 0.0376 (1) | |
O1 | 0.1609 (3) | −0.12739 (17) | 0.79790 (12) | 0.0527 (5) | |
O2 | 0.5576 (3) | −0.23467 (15) | 0.78809 (13) | 0.0581 (5) | |
O3 | 0.4115 (2) | −0.04746 (15) | 0.88447 (10) | 0.0435 (4) | |
C1 | 0.4596 (3) | 0.01601 (19) | 0.68580 (14) | 0.0378 (5) | |
C2 | 0.6807 (4) | 0.0115 (3) | 0.6377 (2) | 0.0622 (8) | |
C3 | 0.7329 (5) | 0.1154 (3) | 0.5544 (2) | 0.0723 (9) | |
C4 | 0.5702 (5) | 0.2217 (3) | 0.51779 (17) | 0.0608 (9) | |
C5 | 0.3524 (5) | 0.2257 (3) | 0.5683 (2) | 0.0757 (10) | |
C6 | 0.2961 (4) | 0.1231 (3) | 0.6517 (2) | 0.0627 (8) | |
C7 | 0.6330 (7) | 0.3319 (4) | 0.4260 (2) | 0.0936 (13) | |
N11 | 1.1098 (3) | 0.81485 (16) | 0.10916 (13) | 0.0404 (5) | |
N81 | 0.8164 (3) | 0.87545 (17) | −0.03296 (13) | 0.0384 (5) | |
C21 | 1.2512 (4) | 0.7857 (2) | 0.17622 (18) | 0.0512 (7) | |
C31 | 1.2863 (4) | 0.6575 (3) | 0.24472 (19) | 0.0571 (8) | |
C41 | 1.1705 (4) | 0.5547 (2) | 0.24159 (17) | 0.0513 (7) | |
C51 | 0.8890 (4) | 0.4787 (2) | 0.16153 (17) | 0.0490 (6) | |
C61 | 0.7435 (4) | 0.5092 (2) | 0.09254 (19) | 0.0544 (8) | |
C71 | 0.7168 (4) | 0.6410 (2) | 0.02750 (17) | 0.0473 (6) | |
C81 | 0.8385 (3) | 0.73882 (18) | 0.03510 (14) | 0.0352 (5) | |
C91 | 0.9915 (3) | 0.71256 (18) | 0.10641 (13) | 0.0340 (5) | |
C101 | 1.0166 (3) | 0.57887 (19) | 0.17142 (14) | 0.0401 (5) | |
H2 | 0.796200 | −0.063000 | 0.6610 | 0.0740* | |
H3 | 0.887700 | 0.112900 | 0.5219 | 0.0850* | |
H5 | 0.237200 | 0.301100 | 0.5458 | 0.0890* | |
H6 | 0.142100 | 0.125700 | 0.6845 | 0.0750* | |
H7A | 0.790700 | 0.338100 | 0.4196 | 0.1120* | |
H7B | 0.607400 | 0.308800 | 0.3645 | 0.1120* | |
H7C | 0.546600 | 0.421200 | 0.4349 | 0.1120* | |
H21 | 1.334200 | 0.8566 | 0.179700 | 0.0600* | |
H31 | 1.390200 | 0.6429 | 0.292900 | 0.0670* | |
H41 | 1.192700 | 0.4662 | 0.286700 | 0.0600* | |
H51 | 0.906300 | 0.3883 | 0.204500 | 0.0570* | |
H61 | 0.657700 | 0.4403 | 0.087500 | 0.0640* | |
H71 | 0.613900 | 0.6615 | −0.022100 | 0.0560* | |
H81A | 0.683 (4) | 0.890 (2) | −0.0639 (17) | 0.044 (6)* | |
H81B | 0.813 (4) | 0.940 (3) | 0.004 (2) | 0.058 (7)* | |
H81C | 0.946 (5) | 0.880 (3) | −0.087 (2) | 0.064 (8)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0423 (3) | 0.0324 (2) | 0.0378 (2) | −0.0111 (2) | −0.0040 (2) | −0.0029 (2) |
O1 | 0.0530 (9) | 0.0577 (9) | 0.0521 (8) | −0.0275 (7) | −0.0065 (7) | −0.0043 (7) |
O2 | 0.0669 (10) | 0.0357 (8) | 0.0629 (10) | 0.0022 (7) | −0.0032 (8) | −0.0052 (7) |
O3 | 0.0502 (8) | 0.0452 (8) | 0.0364 (7) | −0.0115 (6) | −0.0076 (6) | −0.0055 (6) |
C1 | 0.0449 (10) | 0.0370 (9) | 0.0324 (8) | −0.0117 (8) | −0.0034 (7) | −0.0057 (7) |
C2 | 0.0520 (13) | 0.0526 (13) | 0.0663 (15) | −0.0034 (10) | 0.0119 (11) | 0.0011 (11) |
C3 | 0.0703 (17) | 0.0682 (16) | 0.0636 (16) | −0.0194 (14) | 0.0251 (13) | −0.0027 (13) |
C4 | 0.0915 (19) | 0.0584 (14) | 0.0346 (10) | −0.0299 (13) | −0.0042 (11) | −0.0011 (10) |
C5 | 0.0765 (18) | 0.0722 (17) | 0.0653 (16) | −0.0113 (14) | −0.0207 (14) | 0.0257 (14) |
C6 | 0.0481 (12) | 0.0695 (16) | 0.0574 (14) | −0.0080 (11) | −0.0070 (10) | 0.0161 (12) |
C7 | 0.151 (3) | 0.082 (2) | 0.0469 (14) | −0.053 (2) | −0.0025 (17) | 0.0118 (14) |
N11 | 0.0455 (9) | 0.0327 (8) | 0.0442 (9) | −0.0115 (7) | −0.0077 (7) | −0.0042 (6) |
N81 | 0.0445 (9) | 0.0309 (8) | 0.0407 (8) | −0.0102 (7) | −0.0108 (7) | −0.0007 (6) |
C21 | 0.0564 (13) | 0.0436 (11) | 0.0601 (13) | −0.0151 (10) | −0.0185 (10) | −0.0087 (10) |
C31 | 0.0632 (14) | 0.0544 (13) | 0.0553 (13) | −0.0028 (11) | −0.0245 (11) | −0.0059 (10) |
C41 | 0.0640 (14) | 0.0391 (10) | 0.0451 (11) | −0.0022 (9) | −0.0109 (10) | 0.0019 (9) |
C51 | 0.0648 (13) | 0.0313 (9) | 0.0465 (11) | −0.0159 (9) | 0.0028 (10) | 0.0002 (8) |
C61 | 0.0633 (14) | 0.0392 (11) | 0.0648 (14) | −0.0274 (10) | −0.0041 (11) | −0.0056 (10) |
C71 | 0.0499 (11) | 0.0443 (11) | 0.0517 (11) | −0.0187 (9) | −0.0085 (9) | −0.0066 (9) |
C81 | 0.0390 (9) | 0.0291 (8) | 0.0357 (9) | −0.0087 (7) | 0.0003 (7) | −0.0042 (7) |
C91 | 0.0373 (9) | 0.0286 (8) | 0.0344 (8) | −0.0072 (7) | 0.0006 (7) | −0.0055 (7) |
C101 | 0.0482 (10) | 0.0301 (9) | 0.0376 (9) | −0.0061 (7) | 0.0025 (8) | −0.0045 (7) |
Geometric parameters (Å, º) top
S1—O1 | 1.452 (2) | C6—H6 | 0.9576 |
S1—O2 | 1.4425 (17) | C7—H7B | 0.9478 |
S1—O3 | 1.4719 (15) | C7—H7C | 0.9531 |
S1—C1 | 1.771 (2) | C7—H7A | 0.9625 |
N11—C91 | 1.364 (3) | C21—C31 | 1.409 (4) |
N11—C21 | 1.312 (3) | C31—C41 | 1.359 (4) |
N81—C81 | 1.464 (2) | C41—C101 | 1.405 (3) |
N81—H81B | 0.88 (3) | C51—C101 | 1.415 (3) |
N81—H81C | 0.97 (3) | C51—C61 | 1.350 (3) |
N81—H81A | 0.95 (2) | C61—C71 | 1.410 (3) |
C1—C6 | 1.371 (3) | C71—C81 | 1.360 (3) |
C1—C2 | 1.378 (3) | C81—C91 | 1.411 (3) |
C2—C3 | 1.389 (4) | C91—C101 | 1.424 (3) |
C3—C4 | 1.374 (4) | C21—H21 | 0.9556 |
C4—C5 | 1.371 (4) | C31—H31 | 0.9588 |
C4—C7 | 1.513 (4) | C41—H41 | 0.9575 |
C5—C6 | 1.388 (4) | C51—H51 | 0.9573 |
C2—H2 | 0.9588 | C61—H61 | 0.9572 |
C3—H3 | 0.9609 | C71—H71 | 0.9636 |
C5—H5 | 0.9594 | | |
| | | |
O1—S1—O2 | 114.4 (3) | C4—C7—H7B | 110.70 |
O1—S1—O3 | 111.4 (3) | C4—C7—H7C | 110.29 |
O1—S1—C1 | 106.6 (3) | H7A—C7—H7B | 108.60 |
O2—S1—O3 | 111.5 (3) | H7A—C7—H7C | 108.13 |
O2—S1—C1 | 107.0 (3) | H7B—C7—H7C | 109.39 |
O3—S1—C1 | 105.3 (3) | N11—C21—C31 | 124.4 (4) |
C21—N11—C91 | 116.8 (3) | C21—C31—C41 | 119.0 (4) |
H81B—N81—H81C | 108 (2) | C31—C41—C101 | 119.5 (4) |
C81—N81—H81C | 110.6 (18) | C61—C51—C101 | 120.8 (4) |
C81—N81—H81B | 108.0 (18) | C51—C61—C71 | 120.9 (4) |
C81—N81—H81A | 109.6 (13) | C61—C71—C81 | 119.4 (4) |
H81A—N81—H81B | 112 (2) | N81—C81—C91 | 117.8 (3) |
H81A—N81—H81C | 109 (2) | N81—C81—C71 | 120.3 (3) |
S1—C1—C6 | 120.4 (3) | C71—C81—C91 | 121.9 (3) |
C2—C1—C6 | 119.7 (4) | N11—C91—C101 | 123.2 (3) |
S1—C1—C2 | 119.7 (3) | N11—C91—C81 | 118.9 (3) |
C1—C2—C3 | 119.0 (4) | C81—C91—C101 | 118.0 (3) |
C2—C3—C4 | 122.0 (4) | C51—C101—C91 | 119.0 (3) |
C3—C4—C5 | 117.9 (4) | C41—C101—C51 | 124.0 (4) |
C3—C4—C7 | 120.5 (4) | C41—C101—C91 | 117.0 (3) |
C5—C4—C7 | 121.6 (4) | N11—C21—H21 | 117.92 |
C4—C5—C6 | 121.2 (4) | C31—C21—H21 | 117.70 |
C1—C6—C5 | 120.2 (4) | C21—C31—H31 | 120.56 |
C1—C2—H2 | 120.32 | C41—C31—H31 | 120.42 |
C3—C2—H2 | 120.64 | C31—C41—H41 | 120.67 |
C4—C3—H3 | 119.24 | C101—C41—H41 | 119.78 |
C2—C3—H3 | 118.79 | C61—C51—H51 | 119.78 |
C4—C5—H5 | 119.34 | C101—C51—H51 | 119.37 |
C6—C5—H5 | 119.51 | C51—C61—H61 | 119.56 |
C1—C6—H6 | 119.80 | C71—C61—H61 | 119.53 |
C5—C6—H6 | 120.01 | C61—C71—H71 | 120.36 |
C4—C7—H7A | 109.68 | C81—C71—H71 | 120.27 |
| | | |
O1—S1—C1—C2 | −151.2 (4) | N11—C21—C31—C41 | 1.0 (5) |
O1—S1—C1—C6 | 33.1 (4) | C21—C31—C41—C101 | −0.9 (5) |
O2—S1—C1—C2 | −28.4 (4) | C31—C41—C101—C51 | 179.6 (4) |
O2—S1—C1—C6 | 156.0 (4) | C31—C41—C101—C91 | 0.1 (4) |
O3—S1—C1—C2 | 90.4 (4) | C101—C51—C61—C71 | 0.8 (5) |
O3—S1—C1—C6 | −85.3 (4) | C61—C51—C101—C41 | 179.8 (4) |
C21—N11—C91—C81 | −179.6 (4) | C61—C51—C101—C91 | −0.8 (4) |
C21—N11—C91—C101 | −0.4 (4) | C51—C61—C71—C81 | −0.5 (5) |
C91—N11—C21—C31 | −0.4 (4) | C61—C71—C81—C91 | 0.0 (4) |
C2—C1—C6—C5 | 0.8 (5) | C61—C71—C81—N81 | 178.9 (4) |
C6—C1—C2—C3 | −0.7 (5) | N81—C81—C91—N11 | 0.4 (4) |
S1—C1—C6—C5 | 176.4 (4) | N81—C81—C91—C101 | −178.9 (3) |
S1—C1—C2—C3 | −176.4 (4) | C71—C81—C91—N11 | 179.3 (4) |
C1—C2—C3—C4 | −0.7 (5) | C71—C81—C91—C101 | 0.1 (4) |
C2—C3—C4—C5 | 2.1 (5) | N11—C91—C101—C41 | 0.6 (4) |
C2—C3—C4—C7 | −179.2 (4) | C81—C91—C101—C41 | 179.8 (3) |
C3—C4—C5—C6 | −2.1 (5) | N11—C91—C101—C51 | −178.9 (4) |
C7—C4—C5—C6 | 179.2 (4) | C81—C91—C101—C51 | 0.3 (4) |
C4—C5—C6—C1 | 0.7 (5) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N81—H81A···O3i | 0.95 (2) | 1.86 (2) | 2.800 (2) | 168.6 (18) |
N81—H81B···O3ii | 0.88 (3) | 2.14 (3) | 2.868 (2) | 140 (2) |
N81—H81C···O1iii | 0.97 (3) | 1.83 (3) | 2.791 (3) | 169 (3) |
C21—H21···O3iv | 0.96 | 2.59 | 3.494 (3) | 158 |
Symmetry codes: (i) x, y+1, z−1; (ii) −x+1, −y+1, −z+1; (iii) x+1, y+1, z−1; (iv) −x+2, −y+1, −z+1. |
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