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The essentially planar quinoline fragment and the aromatic ring of the toluenesulfonate group of the title compound, C
16H
14N
2O
3S, form a dihedral angle of 52.2 (1)°; the torsion angle about the central bridge C—O—S—C is −69.3 (2)°. The N—H
N and N—H
O hydrogen bonds, involving the H atoms of the amino group and the quinoline and sulfonyl N and O atoms [N
N = 3.055 (3) Å and N
O = 3.058 (2) Å], link the molecules into dimers; a C—H
O interaction formed by the CH group in position 4 of the quinoline group [C
O = 3.293 (3) Å] further links the dimers into infinite chains running along the diagonal of the
ab plane.
Supporting information
CCDC reference: 634085
Key indicators
- Single-crystal X-ray study
- T = 299 K
- Mean (C-C)= 0.004 Å
- R factor = 0.042
- wR factor = 0.119
- Data-to-parameter ratio = 11.3
checkCIF/PLATON results
No syntax errors found
No errors found in this datablock
Data collection: CAD-4-PC Software (Enraf–Nonius, 1996); cell refinement: CAD-4-PC Software; data reduction: REDU4 (Stoe & Cie, 1987); 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: SHELXL97.
2-Aminoquinolin-8-yl 4-
p-toluenesulfonate
top
Crystal data top
C16H14N2O3S | Z = 2 |
Mr = 314.35 | F(000) = 328 |
Triclinic, P1 | Dx = 1.408 Mg m−3 |
Hall symbol: -P 1 | Cu Kα radiation, λ = 1.54180 Å |
a = 8.334 (1) Å | Cell parameters from 25 reflections |
b = 8.636 (1) Å | θ = 7.1–23.3° |
c = 11.805 (1) Å | µ = 2.07 mm−1 |
α = 96.35 (1)° | T = 299 K |
β = 110.23 (1)° | Prism, colourless |
γ = 106.90 (1)° | 0.30 × 0.25 × 0.15 mm |
V = 741.40 (16) Å3 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | 2178 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.012 |
Graphite monochromator | θmax = 66.9°, θmin = 4.1° |
ω/2θ scans | h = −9→9 |
Absorption correction: ψ scan (North et al., 1968) | k = −10→1 |
Tmin = 0.601, Tmax = 0.739 | l = −13→14 |
2829 measured reflections | 3 standard reflections every 120 min |
2632 independent reflections | intensity decay: 1.5% |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.119 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0732P)2 + 0.1575P] where P = (Fo2 + 2Fc2)/3 |
2632 reflections | (Δ/σ)max = 0.017 |
232 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.38 e Å−3 |
Special details top
Experimental. 1H NMR (CDCl3, 300 MHz) \d 2.37 (s, 3H), 5.83 (s, br, 2H), 6.76 (d, J= 8.9 Hz, 1H), 7.47–7.26 (m, 4H), 7.49 (dd, J= 8 Hz, 1H), 7.84 (t; J= 8 Hz, 3H). |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
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 | |
C1 | 0.2135 (3) | 0.2224 (2) | 0.3410 (2) | 0.0430 (5) | |
C2 | 0.2769 (3) | 0.1115 (3) | 0.2951 (2) | 0.0546 (6) | |
H2 | 0.391 (4) | 0.159 (3) | 0.287 (2) | 0.066* | |
C3 | 0.1782 (4) | −0.0585 (3) | 0.2628 (3) | 0.0609 (7) | |
H3 | 0.217 (4) | −0.134 (4) | 0.236 (3) | 0.073* | |
C4 | 0.0182 (4) | −0.1144 (3) | 0.2786 (2) | 0.0558 (6) | |
H4 | −0.048 (4) | −0.224 (4) | 0.257 (2) | 0.067* | |
C5 | −0.0471 (3) | −0.0029 (3) | 0.3281 (2) | 0.0454 (5) | |
C6 | −0.2086 (3) | −0.0551 (3) | 0.3508 (2) | 0.0510 (5) | |
H6 | −0.278 (4) | −0.169 (3) | 0.329 (2) | 0.061* | |
C7 | −0.2598 (3) | 0.0557 (3) | 0.4045 (2) | 0.0514 (5) | |
H7 | −0.359 (4) | 0.024 (3) | 0.424 (2) | 0.062* | |
C8 | −0.1490 (3) | 0.2278 (3) | 0.4399 (2) | 0.0450 (5) | |
C9 | 0.0518 (3) | 0.1708 (2) | 0.36263 (18) | 0.0395 (4) | |
C10 | 0.4171 (3) | 0.4244 (3) | 0.1875 (2) | 0.0454 (5) | |
C11 | 0.3155 (4) | 0.3257 (4) | 0.0689 (2) | 0.0629 (7) | |
H11 | 0.184 (4) | 0.296 (3) | 0.030 (3) | 0.075* | |
C12 | 0.4034 (4) | 0.2621 (4) | 0.0067 (3) | 0.0715 (8) | |
H12 | 0.331 (4) | 0.192 (4) | −0.073 (3) | 0.086* | |
C13 | 0.5896 (4) | 0.2950 (3) | 0.0592 (3) | 0.0604 (6) | |
C14 | 0.6885 (3) | 0.3952 (3) | 0.1785 (2) | 0.0543 (6) | |
H14 | 0.811 (4) | 0.408 (3) | 0.219 (2) | 0.065* | |
C15 | 0.6043 (3) | 0.4607 (3) | 0.2428 (2) | 0.0479 (5) | |
H15 | 0.676 (3) | 0.526 (3) | 0.325 (2) | 0.058* | |
C16 | 0.6813 (5) | 0.2218 (4) | −0.0108 (3) | 0.0907 (10) | |
H16A | 0.7613 | 0.1756 | 0.0427 | 0.109* | |
H16B | 0.7508 | 0.3075 | −0.0382 | 0.109* | |
H16C | 0.5901 | 0.1358 | −0.0815 | 0.109* | |
N1 | 0.0015 (2) | 0.2852 (2) | 0.41811 (16) | 0.0416 (4) | |
N2 | −0.1992 (3) | 0.3379 (3) | 0.4966 (2) | 0.0602 (6) | |
H21N | −0.137 (4) | 0.461 (4) | 0.523 (3) | 0.072* | |
H22N | −0.290 (4) | 0.296 (4) | 0.513 (3) | 0.072* | |
O1 | 0.4218 (2) | 0.66396 (19) | 0.34455 (18) | 0.0622 (5) | |
O2 | 0.1240 (2) | 0.4642 (2) | 0.19554 (18) | 0.0660 (5) | |
O3 | 0.31945 (19) | 0.39402 (17) | 0.37687 (14) | 0.0468 (4) | |
S1 | 0.30965 (7) | 0.49864 (7) | 0.27342 (6) | 0.0484 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0430 (11) | 0.0381 (11) | 0.0509 (12) | 0.0125 (8) | 0.0244 (9) | 0.0084 (9) |
C2 | 0.0549 (13) | 0.0533 (14) | 0.0706 (16) | 0.0241 (11) | 0.0381 (12) | 0.0143 (11) |
C3 | 0.0729 (16) | 0.0491 (14) | 0.0757 (17) | 0.0297 (12) | 0.0418 (14) | 0.0087 (12) |
C4 | 0.0647 (15) | 0.0380 (12) | 0.0622 (14) | 0.0144 (11) | 0.0282 (12) | 0.0028 (11) |
C5 | 0.0473 (12) | 0.0381 (11) | 0.0490 (11) | 0.0111 (9) | 0.0213 (10) | 0.0070 (9) |
C6 | 0.0490 (12) | 0.0386 (12) | 0.0589 (14) | 0.0043 (10) | 0.0247 (11) | 0.0066 (10) |
C7 | 0.0459 (12) | 0.0493 (13) | 0.0627 (14) | 0.0083 (10) | 0.0326 (11) | 0.0137 (10) |
C8 | 0.0476 (12) | 0.0443 (11) | 0.0500 (12) | 0.0138 (9) | 0.0291 (10) | 0.0120 (9) |
C9 | 0.0417 (11) | 0.0364 (10) | 0.0430 (10) | 0.0124 (8) | 0.0213 (9) | 0.0083 (8) |
C10 | 0.0442 (11) | 0.0466 (12) | 0.0570 (13) | 0.0176 (9) | 0.0318 (10) | 0.0141 (10) |
C11 | 0.0482 (13) | 0.0787 (18) | 0.0592 (15) | 0.0215 (12) | 0.0220 (12) | 0.0065 (13) |
C12 | 0.0737 (18) | 0.089 (2) | 0.0514 (14) | 0.0292 (16) | 0.0275 (14) | 0.0021 (14) |
C13 | 0.0658 (16) | 0.0657 (16) | 0.0696 (16) | 0.0300 (13) | 0.0440 (13) | 0.0178 (13) |
C14 | 0.0476 (13) | 0.0593 (14) | 0.0687 (15) | 0.0228 (11) | 0.0345 (12) | 0.0162 (12) |
C15 | 0.0434 (11) | 0.0484 (12) | 0.0573 (13) | 0.0146 (9) | 0.0282 (10) | 0.0100 (10) |
C16 | 0.105 (3) | 0.101 (2) | 0.097 (2) | 0.049 (2) | 0.069 (2) | 0.0112 (19) |
N1 | 0.0426 (9) | 0.0377 (9) | 0.0506 (10) | 0.0117 (7) | 0.0282 (8) | 0.0089 (7) |
N2 | 0.0659 (13) | 0.0496 (12) | 0.0840 (15) | 0.0163 (10) | 0.0566 (12) | 0.0104 (10) |
O1 | 0.0691 (11) | 0.0399 (8) | 0.0957 (13) | 0.0133 (8) | 0.0598 (10) | 0.0120 (8) |
O2 | 0.0502 (10) | 0.0862 (13) | 0.0828 (12) | 0.0351 (9) | 0.0384 (9) | 0.0320 (10) |
O3 | 0.0451 (8) | 0.0408 (8) | 0.0577 (9) | 0.0077 (6) | 0.0320 (7) | 0.0060 (7) |
S1 | 0.0452 (3) | 0.0466 (3) | 0.0691 (4) | 0.0178 (2) | 0.0391 (3) | 0.0156 (3) |
Geometric parameters (Å, º) top
C1—C2 | 1.367 (3) | C10—C15 | 1.388 (3) |
C1—C9 | 1.412 (3) | C10—S1 | 1.750 (2) |
C1—O3 | 1.413 (2) | C11—C12 | 1.376 (4) |
C2—C3 | 1.390 (4) | C11—H11 | 0.97 (3) |
C2—H2 | 0.97 (3) | C12—C13 | 1.384 (4) |
C3—C4 | 1.364 (4) | C12—H12 | 0.94 (3) |
C3—H3 | 0.88 (3) | C13—C14 | 1.387 (4) |
C4—C5 | 1.402 (3) | C13—C16 | 1.505 (3) |
C4—H4 | 0.90 (3) | C14—C15 | 1.375 (3) |
C5—C6 | 1.417 (3) | C14—H14 | 0.93 (3) |
C5—C9 | 1.417 (3) | C15—H15 | 0.95 (3) |
C6—C7 | 1.338 (3) | C16—H16A | 0.9600 |
C6—H6 | 0.94 (3) | C16—H16B | 0.9600 |
C7—C8 | 1.426 (3) | C16—H16C | 0.9600 |
C7—H7 | 0.90 (3) | N2—H21N | 0.99 (3) |
C8—N1 | 1.332 (3) | N2—H22N | 0.84 (3) |
C8—N2 | 1.346 (3) | O1—S1 | 1.4259 (17) |
C9—N1 | 1.367 (2) | O2—S1 | 1.4197 (18) |
C10—C11 | 1.378 (3) | O3—S1 | 1.5913 (16) |
| | | |
C2—C1—C9 | 122.2 (2) | C12—C11—H11 | 119.0 (17) |
C2—C1—O3 | 119.20 (19) | C10—C11—H11 | 122.3 (17) |
C9—C1—O3 | 118.39 (17) | C11—C12—C13 | 122.1 (3) |
C1—C2—C3 | 120.3 (2) | C11—C12—H12 | 117.1 (19) |
C1—C2—H2 | 115.9 (16) | C13—C12—H12 | 120.8 (19) |
C3—C2—H2 | 123.8 (15) | C12—C13—C14 | 118.1 (2) |
C4—C3—C2 | 119.7 (2) | C12—C13—C16 | 120.8 (3) |
C4—C3—H3 | 117.3 (19) | C14—C13—C16 | 121.2 (2) |
C2—C3—H3 | 123.0 (19) | C15—C14—C13 | 121.1 (2) |
C3—C4—C5 | 120.9 (2) | C15—C14—H14 | 119.2 (17) |
C3—C4—H4 | 120.5 (17) | C13—C14—H14 | 119.3 (17) |
C5—C4—H4 | 118.6 (18) | C14—C15—C10 | 119.2 (2) |
C4—C5—C6 | 123.0 (2) | C14—C15—H15 | 118.9 (16) |
C4—C5—C9 | 120.6 (2) | C10—C15—H15 | 121.8 (15) |
C6—C5—C9 | 116.34 (19) | C13—C16—H16A | 109.5 |
C7—C6—C5 | 120.8 (2) | C13—C16—H16B | 109.5 |
C7—C6—H6 | 120.7 (16) | H16A—C16—H16B | 109.5 |
C5—C6—H6 | 118.5 (16) | C13—C16—H16C | 109.5 |
C6—C7—C8 | 119.2 (2) | H16A—C16—H16C | 109.5 |
C6—C7—H7 | 122.0 (16) | H16B—C16—H16C | 109.5 |
C8—C7—H7 | 118.7 (16) | C8—N1—C9 | 117.24 (17) |
N1—C8—N2 | 118.3 (2) | C8—N2—H21N | 126.4 (16) |
N1—C8—C7 | 122.95 (19) | C8—N2—H22N | 115 (2) |
N2—C8—C7 | 118.8 (2) | H21N—N2—H22N | 118 (3) |
N1—C9—C1 | 120.22 (18) | C1—O3—S1 | 119.16 (13) |
N1—C9—C5 | 123.48 (18) | O2—S1—O1 | 119.64 (11) |
C1—C9—C5 | 116.25 (18) | O2—S1—O3 | 109.44 (9) |
C11—C10—C15 | 120.9 (2) | O1—S1—O3 | 102.83 (10) |
C11—C10—S1 | 120.24 (18) | O2—S1—C10 | 109.50 (11) |
C15—C10—S1 | 118.81 (18) | O1—S1—C10 | 109.69 (10) |
C12—C11—C10 | 118.6 (2) | O3—S1—C10 | 104.56 (9) |
| | | |
C9—C1—C2—C3 | 2.7 (4) | C11—C12—C13—C14 | 0.1 (5) |
O3—C1—C2—C3 | 177.9 (2) | C11—C12—C13—C16 | 179.3 (3) |
C1—C2—C3—C4 | −0.8 (4) | C12—C13—C14—C15 | −0.2 (4) |
C2—C3—C4—C5 | −0.6 (4) | C16—C13—C14—C15 | −179.4 (3) |
C3—C4—C5—C6 | −177.5 (2) | C13—C14—C15—C10 | 0.6 (4) |
C3—C4—C5—C9 | 0.1 (4) | C11—C10—C15—C14 | −0.8 (4) |
C4—C5—C6—C7 | 176.3 (2) | S1—C10—C15—C14 | 176.43 (18) |
C9—C5—C6—C7 | −1.5 (3) | N2—C8—N1—C9 | 178.8 (2) |
C5—C6—C7—C8 | −0.5 (4) | C7—C8—N1—C9 | −2.0 (3) |
C6—C7—C8—N1 | 2.4 (4) | C1—C9—N1—C8 | −177.6 (2) |
C6—C7—C8—N2 | −178.4 (2) | C5—C9—N1—C8 | −0.1 (3) |
C2—C1—C9—N1 | 174.6 (2) | C2—C1—O3—S1 | 81.6 (2) |
O3—C1—C9—N1 | −0.6 (3) | C9—C1—O3—S1 | −102.99 (19) |
C2—C1—C9—C5 | −3.1 (3) | C1—O3—S1—O2 | 47.93 (16) |
O3—C1—C9—C5 | −178.35 (18) | C1—O3—S1—O1 | 176.11 (14) |
C4—C5—C9—N1 | −176.0 (2) | C1—O3—S1—C10 | −69.29 (16) |
C6—C5—C9—N1 | 1.8 (3) | C11—C10—S1—O2 | −9.4 (2) |
C4—C5—C9—C1 | 1.7 (3) | C15—C10—S1—O2 | 173.36 (17) |
C6—C5—C9—C1 | 179.5 (2) | C11—C10—S1—O1 | −142.5 (2) |
C15—C10—C11—C12 | 0.7 (4) | C15—C10—S1—O1 | 40.2 (2) |
S1—C10—C11—C12 | −176.5 (2) | C11—C10—S1—O3 | 107.8 (2) |
C10—C11—C12—C13 | −0.4 (5) | C15—C10—S1—O3 | −69.46 (19) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H21N···N1i | 0.99 (3) | 2.06 (3) | 3.055 (3) | 178 (2) |
N2—H22N···O1i | 0.84 (3) | 2.35 (3) | 3.058 (2) | 143 (3) |
C6—H6···O1ii | 0.94 (3) | 2.58 (3) | 3.293 (3) | 133 (2) |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x−1, y−1, z. |
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