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The essentially planar quinoline fragment and the aromatic ring of the toluene­sulfonate group of the title compound, C16H14N2O3S, 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806050896/ya2030sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806050896/ya2030Isup2.hkl
Contains datablock I

CCDC reference: 634085

Key indicators

  • Single-crystal X-ray study
  • T = 299 K
  • Mean [sigma](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

Computing details top

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
C16H14N2O3SZ = 2
Mr = 314.35F(000) = 328
Triclinic, P1Dx = 1.408 Mg m3
Hall symbol: -P 1Cu Kα radiation, λ = 1.54180 Å
a = 8.334 (1) ÅCell parameters from 25 reflections
b = 8.636 (1) Åθ = 7.1–23.3°
c = 11.805 (1) ŵ = 2.07 mm1
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 tubeRint = 0.012
Graphite monochromatorθmax = 66.9°, θmin = 4.1°
ω/2θ scansh = 99
Absorption correction: ψ scan
(North et al., 1968)
k = 101
Tmin = 0.601, Tmax = 0.739l = 1314
2829 measured reflections3 standard reflections every 120 min
2632 independent reflections intensity decay: 1.5%
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)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H 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 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.38 e Å3
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
xyzUiso*/Ueq
C10.2135 (3)0.2224 (2)0.3410 (2)0.0430 (5)
C20.2769 (3)0.1115 (3)0.2951 (2)0.0546 (6)
H20.391 (4)0.159 (3)0.287 (2)0.066*
C30.1782 (4)0.0585 (3)0.2628 (3)0.0609 (7)
H30.217 (4)0.134 (4)0.236 (3)0.073*
C40.0182 (4)0.1144 (3)0.2786 (2)0.0558 (6)
H40.048 (4)0.224 (4)0.257 (2)0.067*
C50.0471 (3)0.0029 (3)0.3281 (2)0.0454 (5)
C60.2086 (3)0.0551 (3)0.3508 (2)0.0510 (5)
H60.278 (4)0.169 (3)0.329 (2)0.061*
C70.2598 (3)0.0557 (3)0.4045 (2)0.0514 (5)
H70.359 (4)0.024 (3)0.424 (2)0.062*
C80.1490 (3)0.2278 (3)0.4399 (2)0.0450 (5)
C90.0518 (3)0.1708 (2)0.36263 (18)0.0395 (4)
C100.4171 (3)0.4244 (3)0.1875 (2)0.0454 (5)
C110.3155 (4)0.3257 (4)0.0689 (2)0.0629 (7)
H110.184 (4)0.296 (3)0.030 (3)0.075*
C120.4034 (4)0.2621 (4)0.0067 (3)0.0715 (8)
H120.331 (4)0.192 (4)0.073 (3)0.086*
C130.5896 (4)0.2950 (3)0.0592 (3)0.0604 (6)
C140.6885 (3)0.3952 (3)0.1785 (2)0.0543 (6)
H140.811 (4)0.408 (3)0.219 (2)0.065*
C150.6043 (3)0.4607 (3)0.2428 (2)0.0479 (5)
H150.676 (3)0.526 (3)0.325 (2)0.058*
C160.6813 (5)0.2218 (4)0.0108 (3)0.0907 (10)
H16A0.76130.17560.04270.109*
H16B0.75080.30750.03820.109*
H16C0.59010.13580.08150.109*
N10.0015 (2)0.2852 (2)0.41811 (16)0.0416 (4)
N20.1992 (3)0.3379 (3)0.4966 (2)0.0602 (6)
H21N0.137 (4)0.461 (4)0.523 (3)0.072*
H22N0.290 (4)0.296 (4)0.513 (3)0.072*
O10.4218 (2)0.66396 (19)0.34455 (18)0.0622 (5)
O20.1240 (2)0.4642 (2)0.19554 (18)0.0660 (5)
O30.31945 (19)0.39402 (17)0.37687 (14)0.0468 (4)
S10.30965 (7)0.49864 (7)0.27342 (6)0.0484 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0430 (11)0.0381 (11)0.0509 (12)0.0125 (8)0.0244 (9)0.0084 (9)
C20.0549 (13)0.0533 (14)0.0706 (16)0.0241 (11)0.0381 (12)0.0143 (11)
C30.0729 (16)0.0491 (14)0.0757 (17)0.0297 (12)0.0418 (14)0.0087 (12)
C40.0647 (15)0.0380 (12)0.0622 (14)0.0144 (11)0.0282 (12)0.0028 (11)
C50.0473 (12)0.0381 (11)0.0490 (11)0.0111 (9)0.0213 (10)0.0070 (9)
C60.0490 (12)0.0386 (12)0.0589 (14)0.0043 (10)0.0247 (11)0.0066 (10)
C70.0459 (12)0.0493 (13)0.0627 (14)0.0083 (10)0.0326 (11)0.0137 (10)
C80.0476 (12)0.0443 (11)0.0500 (12)0.0138 (9)0.0291 (10)0.0120 (9)
C90.0417 (11)0.0364 (10)0.0430 (10)0.0124 (8)0.0213 (9)0.0083 (8)
C100.0442 (11)0.0466 (12)0.0570 (13)0.0176 (9)0.0318 (10)0.0141 (10)
C110.0482 (13)0.0787 (18)0.0592 (15)0.0215 (12)0.0220 (12)0.0065 (13)
C120.0737 (18)0.089 (2)0.0514 (14)0.0292 (16)0.0275 (14)0.0021 (14)
C130.0658 (16)0.0657 (16)0.0696 (16)0.0300 (13)0.0440 (13)0.0178 (13)
C140.0476 (13)0.0593 (14)0.0687 (15)0.0228 (11)0.0345 (12)0.0162 (12)
C150.0434 (11)0.0484 (12)0.0573 (13)0.0146 (9)0.0282 (10)0.0100 (10)
C160.105 (3)0.101 (2)0.097 (2)0.049 (2)0.069 (2)0.0112 (19)
N10.0426 (9)0.0377 (9)0.0506 (10)0.0117 (7)0.0282 (8)0.0089 (7)
N20.0659 (13)0.0496 (12)0.0840 (15)0.0163 (10)0.0566 (12)0.0104 (10)
O10.0691 (11)0.0399 (8)0.0957 (13)0.0133 (8)0.0598 (10)0.0120 (8)
O20.0502 (10)0.0862 (13)0.0828 (12)0.0351 (9)0.0384 (9)0.0320 (10)
O30.0451 (8)0.0408 (8)0.0577 (9)0.0077 (6)0.0320 (7)0.0060 (7)
S10.0452 (3)0.0466 (3)0.0691 (4)0.0178 (2)0.0391 (3)0.0156 (3)
Geometric parameters (Å, º) top
C1—C21.367 (3)C10—C151.388 (3)
C1—C91.412 (3)C10—S11.750 (2)
C1—O31.413 (2)C11—C121.376 (4)
C2—C31.390 (4)C11—H110.97 (3)
C2—H20.97 (3)C12—C131.384 (4)
C3—C41.364 (4)C12—H120.94 (3)
C3—H30.88 (3)C13—C141.387 (4)
C4—C51.402 (3)C13—C161.505 (3)
C4—H40.90 (3)C14—C151.375 (3)
C5—C61.417 (3)C14—H140.93 (3)
C5—C91.417 (3)C15—H150.95 (3)
C6—C71.338 (3)C16—H16A0.9600
C6—H60.94 (3)C16—H16B0.9600
C7—C81.426 (3)C16—H16C0.9600
C7—H70.90 (3)N2—H21N0.99 (3)
C8—N11.332 (3)N2—H22N0.84 (3)
C8—N21.346 (3)O1—S11.4259 (17)
C9—N11.367 (2)O2—S11.4197 (18)
C10—C111.378 (3)O3—S11.5913 (16)
C2—C1—C9122.2 (2)C12—C11—H11119.0 (17)
C2—C1—O3119.20 (19)C10—C11—H11122.3 (17)
C9—C1—O3118.39 (17)C11—C12—C13122.1 (3)
C1—C2—C3120.3 (2)C11—C12—H12117.1 (19)
C1—C2—H2115.9 (16)C13—C12—H12120.8 (19)
C3—C2—H2123.8 (15)C12—C13—C14118.1 (2)
C4—C3—C2119.7 (2)C12—C13—C16120.8 (3)
C4—C3—H3117.3 (19)C14—C13—C16121.2 (2)
C2—C3—H3123.0 (19)C15—C14—C13121.1 (2)
C3—C4—C5120.9 (2)C15—C14—H14119.2 (17)
C3—C4—H4120.5 (17)C13—C14—H14119.3 (17)
C5—C4—H4118.6 (18)C14—C15—C10119.2 (2)
C4—C5—C6123.0 (2)C14—C15—H15118.9 (16)
C4—C5—C9120.6 (2)C10—C15—H15121.8 (15)
C6—C5—C9116.34 (19)C13—C16—H16A109.5
C7—C6—C5120.8 (2)C13—C16—H16B109.5
C7—C6—H6120.7 (16)H16A—C16—H16B109.5
C5—C6—H6118.5 (16)C13—C16—H16C109.5
C6—C7—C8119.2 (2)H16A—C16—H16C109.5
C6—C7—H7122.0 (16)H16B—C16—H16C109.5
C8—C7—H7118.7 (16)C8—N1—C9117.24 (17)
N1—C8—N2118.3 (2)C8—N2—H21N126.4 (16)
N1—C8—C7122.95 (19)C8—N2—H22N115 (2)
N2—C8—C7118.8 (2)H21N—N2—H22N118 (3)
N1—C9—C1120.22 (18)C1—O3—S1119.16 (13)
N1—C9—C5123.48 (18)O2—S1—O1119.64 (11)
C1—C9—C5116.25 (18)O2—S1—O3109.44 (9)
C11—C10—C15120.9 (2)O1—S1—O3102.83 (10)
C11—C10—S1120.24 (18)O2—S1—C10109.50 (11)
C15—C10—S1118.81 (18)O1—S1—C10109.69 (10)
C12—C11—C10118.6 (2)O3—S1—C10104.56 (9)
C9—C1—C2—C32.7 (4)C11—C12—C13—C140.1 (5)
O3—C1—C2—C3177.9 (2)C11—C12—C13—C16179.3 (3)
C1—C2—C3—C40.8 (4)C12—C13—C14—C150.2 (4)
C2—C3—C4—C50.6 (4)C16—C13—C14—C15179.4 (3)
C3—C4—C5—C6177.5 (2)C13—C14—C15—C100.6 (4)
C3—C4—C5—C90.1 (4)C11—C10—C15—C140.8 (4)
C4—C5—C6—C7176.3 (2)S1—C10—C15—C14176.43 (18)
C9—C5—C6—C71.5 (3)N2—C8—N1—C9178.8 (2)
C5—C6—C7—C80.5 (4)C7—C8—N1—C92.0 (3)
C6—C7—C8—N12.4 (4)C1—C9—N1—C8177.6 (2)
C6—C7—C8—N2178.4 (2)C5—C9—N1—C80.1 (3)
C2—C1—C9—N1174.6 (2)C2—C1—O3—S181.6 (2)
O3—C1—C9—N10.6 (3)C9—C1—O3—S1102.99 (19)
C2—C1—C9—C53.1 (3)C1—O3—S1—O247.93 (16)
O3—C1—C9—C5178.35 (18)C1—O3—S1—O1176.11 (14)
C4—C5—C9—N1176.0 (2)C1—O3—S1—C1069.29 (16)
C6—C5—C9—N11.8 (3)C11—C10—S1—O29.4 (2)
C4—C5—C9—C11.7 (3)C15—C10—S1—O2173.36 (17)
C6—C5—C9—C1179.5 (2)C11—C10—S1—O1142.5 (2)
C15—C10—C11—C120.7 (4)C15—C10—S1—O140.2 (2)
S1—C10—C11—C12176.5 (2)C11—C10—S1—O3107.8 (2)
C10—C11—C12—C130.4 (5)C15—C10—S1—O369.46 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H21N···N1i0.99 (3)2.06 (3)3.055 (3)178 (2)
N2—H22N···O1i0.84 (3)2.35 (3)3.058 (2)143 (3)
C6—H6···O1ii0.94 (3)2.58 (3)3.293 (3)133 (2)
Symmetry codes: (i) x, y+1, z+1; (ii) x1, y1, z.
 

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