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Acta Cryst. (2007). E63, o3059    [ doi:10.1107/S1600536807025706 ]

N-(4-Methoxybenzyl)quinoline-8-sulfonamide

C. R. Andrighetti-Fröhner, R. J. Nunes, L. E. da Silva, C. M. O. Simões and S. Foro

Abstract top

In the title compound, C17H16N2O3S, the dihedral angle between the planes of the nearly planar quinoline group and the benzene group of the methoxybenzene group is 11.92 (9)°. The C-S-N-C torsion angle is 68.6 (2)°. Both sulfonyl O atoms are involved in weak intermolecular hydrogen bonds of types N-H...O (H...O = 2.41 Å) and C-H...O (H...O = 2.52 Å).

Comment top

The quinoline core is present in many different biological active compounds. We have pursed a pharmacological program to investigate the structure-function relationships, in order to develop antiparasitic and antiviral drugs based on heterocyclic compounds (Andrighetti-Fröhner et al., 2006; da Silva et al., 2007). Our interest in biological active compounds, as potential agents for antiviral diseases (Andrighetti-Fröhner et al., 2003) led to the X-ray study of the title compound, (I).

In the molecule of (I) (Fig. 1) the torsion angle C10—N1—S1—C1 is 68.6 (2)° and the quinoline ring system plane, C1···C9/N2 forms a dihedral angle of 11.92 (9)° with the plane of the benzene group of the methoxybenzene moiety, C11···C16. The quinoline moiety is nearly planar with maximum deviations from the mean plane of −0.0340 (3) Å for atom C7 and 0.0296 (2) Å for atom N2. Two weak intermolecular hydrogen bonds of types N—H···O and C—H···O are observed, which connect molecules to form a three dimensional network (Fig. 2).

Related literature top

For related literature, see: Andrighetti-Fröhner et al. (2003, 2006); da Silva et al. (2006, 2007).

Experimental top

The title compound was prepared according to the literature procedure (da Silva et al., 2006). Single crystals suitable for X-ray data collection were obtained by recrystallization from a methanol-dichloromethane solution (1:1).

Refinement top

H atoms were positioned with idealized geometry and refined using a riding model with C—H and N—H bond lengths constrained to 0.93–0.97 and 0.86 Å, respectively. Their isotropic displacement parameters were set equal to 1.2Ueq (parent atom).

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.

Figures top
[Figure 1] Fig. 1. Molecular structure of (I), showing the atom labeling and displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. Molecular packing of (I) with hydrogen bonds shown as dashed lines.
N-(4-Methoxybenzyl)quinoline-8-sulfonamide top
Crystal data top
C17H16N2O3SF000 = 688
Mr = 328.38Dx = 1.427 Mg m−3
Orthorhombic, P212121Cu Kα radiation
λ = 1.54180 Å
Hall symbol: P 2ac 2abCell parameters from 25 reflections
a = 7.273 (1) Åθ = 6.4–18.8º
b = 9.146 (1) ŵ = 2.03 mm−1
c = 22.975 (3) ÅT = 299 (2) K
V = 1528.3 (3) Å3Prism, colourless
Z = 40.65 × 0.40 × 0.35 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer		Rint = 0.075
Radiation source: fine-focus sealed tubeθmax = 67.0º
Monochromator: graphiteθmin = 3.9º
T = 299(2) Kh = 0→8
ω/2θ scansk = −10→10
Absorption correction: nonel = −27→0
3007 measured reflections3 standard reflections
2724 independent reflections every 120 min
2684 reflections with I > 2σ(I) intensity decay: 1.0%
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: full  w = 1/[σ2(Fo2) + (0.08P)2 + 0.3281P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.044(Δ/σ)max = 0.005
wR(F2) = 0.120Δρmax = 0.37 e Å−3
S = 1.11Δρmin = −0.26 e Å−3
2724 reflectionsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
210 parametersExtinction coefficient: 0.0078 (8)
Primary atom site location: structure-invariant direct methodsAbsolute structure: (Flack, 1983), 1125 Friedel pairs
Secondary atom site location: difference Fourier mapFlack parameter: 0.02 (2)
Hydrogen site location: inferred from neighbouring sites
Crystal data top
C17H16N2O3SV = 1528.3 (3) Å3
Mr = 328.38Z = 4
Orthorhombic, P212121Cu Kα
a = 7.273 (1) ŵ = 2.03 mm−1
b = 9.146 (1) ÅT = 299 (2) K
c = 22.975 (3) Å0.65 × 0.40 × 0.35 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer		Rint = 0.075
Absorption correction: none3 standard reflections
3007 measured reflections every 120 min
2724 independent reflections intensity decay: 1.0%
2684 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.120Δρmax = 0.37 e Å−3
S = 1.11Δρmin = −0.26 e Å−3
2724 reflectionsAbsolute structure: (Flack, 1983), 1125 Friedel pairs
210 parametersFlack parameter: 0.02 (2)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.34694 (9)1.29117 (6)0.09586 (3)0.0453 (2)
O10.3555 (3)1.3926 (2)0.14329 (9)0.0636 (5)
O20.4836 (3)1.2999 (2)0.05121 (9)0.0628 (5)
O3−0.1936 (3)0.7783 (2)0.20022 (8)0.0627 (5)
N10.1504 (3)1.3143 (2)0.06407 (9)0.0488 (5)
H1N0.14551.32040.02670.059*
N20.2562 (3)1.0071 (3)0.03640 (9)0.0502 (5)
C10.3545 (3)1.1131 (3)0.12712 (10)0.0410 (5)
C20.4028 (4)1.1002 (3)0.18424 (11)0.0487 (6)
H20.43291.18310.20570.058*
C30.4070 (4)0.9610 (4)0.21093 (13)0.0572 (7)
H30.44440.95210.24950.069*
C40.3568 (4)0.8407 (3)0.18066 (13)0.0566 (7)
H40.35660.75010.19900.068*
C50.3044 (4)0.8507 (3)0.12124 (12)0.0490 (6)
C60.2484 (4)0.7293 (3)0.08807 (15)0.0636 (8)
H60.24830.63630.10450.076*
C70.1941 (5)0.7485 (4)0.03161 (16)0.0699 (9)
H70.15310.66990.00940.084*
C80.2017 (5)0.8899 (4)0.00795 (13)0.0621 (8)
H80.16560.9016−0.03060.074*
C90.3061 (3)0.9891 (3)0.09362 (11)0.0420 (5)
C10−0.0218 (4)1.3251 (3)0.09868 (14)0.0567 (7)
H10A−0.11881.36200.07370.068*
H10B−0.00331.39570.12960.068*
C11−0.0842 (3)1.1829 (3)0.12522 (11)0.0460 (6)
C12−0.0715 (4)1.1593 (3)0.18508 (12)0.0542 (7)
H12−0.03481.23520.20940.065*
C13−0.1128 (4)1.0248 (3)0.20857 (12)0.0560 (7)
H13−0.10521.01110.24860.067*
C14−0.1650 (4)0.9106 (3)0.17343 (10)0.0456 (5)
C15−0.1858 (4)0.9332 (3)0.11396 (10)0.0462 (5)
H15−0.22580.85780.09000.055*
C16−0.1462 (4)1.0699 (3)0.09090 (10)0.0465 (5)
H16−0.16191.08550.05120.056*
C17−0.2180 (5)0.6546 (4)0.16410 (16)0.0717 (9)
H17A−0.33690.65890.14600.086*
H17B−0.20910.56730.18710.086*
H17C−0.12450.65350.13460.086*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0539 (4)0.0362 (3)0.0458 (3)−0.0037 (3)−0.0012 (3)0.0070 (2)
O10.0878 (15)0.0416 (10)0.0613 (11)−0.0064 (11)−0.0133 (11)−0.0026 (8)
O20.0623 (11)0.0649 (12)0.0612 (11)−0.0104 (10)0.0108 (9)0.0205 (10)
O30.0722 (13)0.0613 (11)0.0545 (10)0.0062 (10)0.0053 (9)0.0184 (9)
N10.0593 (12)0.0399 (10)0.0471 (10)0.0027 (10)−0.0036 (10)0.0098 (8)
N20.0598 (13)0.0480 (12)0.0426 (10)0.0022 (10)0.0044 (9)0.0007 (9)
C10.0408 (11)0.0381 (11)0.0440 (11)0.0049 (10)0.0022 (10)0.0096 (9)
C20.0471 (13)0.0534 (15)0.0457 (13)0.0060 (11)−0.0006 (10)0.0025 (12)
C30.0506 (15)0.0715 (19)0.0495 (14)0.0168 (13)0.0037 (11)0.0238 (14)
C40.0497 (14)0.0528 (14)0.0672 (16)0.0138 (12)0.0106 (13)0.0261 (13)
C50.0430 (12)0.0403 (12)0.0637 (15)0.0098 (10)0.0120 (11)0.0102 (11)
C60.0596 (15)0.0393 (14)0.092 (2)0.0055 (12)0.0213 (16)0.0064 (14)
C70.076 (2)0.0494 (16)0.084 (2)−0.0050 (14)0.0171 (17)−0.0196 (15)
C80.076 (2)0.0584 (17)0.0515 (14)−0.0013 (15)0.0080 (13)−0.0115 (13)
C90.0396 (11)0.0395 (11)0.0469 (12)0.0075 (9)0.0065 (9)0.0055 (10)
C100.0557 (14)0.0413 (13)0.0730 (18)0.0112 (12)−0.0013 (14)0.0025 (13)
C110.0411 (11)0.0440 (14)0.0529 (13)0.0090 (10)0.0003 (10)−0.0015 (11)
C120.0536 (14)0.0598 (16)0.0492 (13)0.0054 (12)−0.0021 (12)−0.0154 (12)
C130.0561 (15)0.0736 (18)0.0385 (12)0.0050 (13)−0.0034 (11)0.0015 (13)
C140.0420 (12)0.0523 (13)0.0427 (12)0.0074 (11)0.0026 (10)0.0076 (10)
C150.0503 (13)0.0480 (13)0.0401 (11)0.0000 (11)−0.0020 (10)−0.0010 (10)
C160.0511 (13)0.0517 (13)0.0367 (11)0.0036 (11)−0.0034 (11)0.0047 (10)
C170.083 (2)0.0505 (16)0.081 (2)0.0083 (15)0.0259 (18)0.0121 (15)
Geometric parameters (Å, °) top
S1—O21.431 (2)C6—H60.9300
S1—O11.433 (2)C7—C81.403 (5)
S1—N11.619 (2)C7—H70.9300
S1—C11.781 (2)C8—H80.9300
O3—C141.373 (3)C10—C111.506 (4)
O3—C171.415 (4)C10—H10A0.9700
N1—C101.486 (4)C10—H10B0.9700
N1—H1N0.8600C11—C161.376 (4)
N2—C81.317 (4)C11—C121.395 (4)
N2—C91.374 (3)C12—C131.377 (4)
C1—C21.364 (3)C12—H120.9300
C1—C91.415 (3)C13—C141.374 (4)
C2—C31.414 (4)C13—H130.9300
C2—H20.9300C14—C151.390 (3)
C3—C41.352 (5)C15—C161.388 (4)
C3—H30.9300C15—H150.9300
C4—C51.420 (4)C16—H160.9300
C4—H40.9300C17—H17A0.9600
C5—C61.407 (4)C17—H17B0.9600
C5—C91.416 (3)C17—H17C0.9600
C6—C71.367 (5)
O2—S1—O1118.60 (14)C7—C8—H8117.6
O2—S1—N1106.43 (12)N2—C9—C1119.3 (2)
O1—S1—N1107.28 (13)N2—C9—C5122.3 (2)
O2—S1—C1108.61 (12)C1—C9—C5118.3 (2)
O1—S1—C1106.51 (11)N1—C10—C11114.4 (2)
N1—S1—C1109.18 (11)N1—C10—H10A108.7
C14—O3—C17117.4 (2)C11—C10—H10A108.7
C10—N1—S1120.73 (18)N1—C10—H10B108.7
C10—N1—H1N119.6C11—C10—H10B108.7
S1—N1—H1N119.6H10A—C10—H10B107.6
C8—N2—C9117.2 (2)C16—C11—C12118.0 (2)
C2—C1—C9121.2 (2)C16—C11—C10121.0 (2)
C2—C1—S1118.4 (2)C12—C11—C10120.8 (3)
C9—C1—S1120.40 (17)C13—C12—C11120.7 (3)
C1—C2—C3120.1 (3)C13—C12—H12119.7
C1—C2—H2120.0C11—C12—H12119.7
C3—C2—H2120.0C14—C13—C12120.6 (2)
C4—C3—C2120.3 (2)C14—C13—H13119.7
C4—C3—H3119.9C12—C13—H13119.7
C2—C3—H3119.9O3—C14—C13116.6 (2)
C3—C4—C5121.0 (2)O3—C14—C15123.7 (2)
C3—C4—H4119.5C13—C14—C15119.6 (2)
C5—C4—H4119.5C16—C15—C14119.1 (2)
C6—C5—C9117.7 (3)C16—C15—H15120.4
C6—C5—C4123.2 (3)C14—C15—H15120.4
C9—C5—C4119.1 (3)C11—C16—C15121.7 (2)
C7—C6—C5119.7 (3)C11—C16—H16119.1
C7—C6—H6120.1C15—C16—H16119.1
C5—C6—H6120.1O3—C17—H17A109.5
C6—C7—C8118.3 (3)O3—C17—H17B109.5
C6—C7—H7120.8H17A—C17—H17B109.5
C8—C7—H7120.8O3—C17—H17C109.5
N2—C8—C7124.7 (3)H17A—C17—H17C109.5
N2—C8—H8117.6H17B—C17—H17C109.5
O2—S1—N1—C10−174.4 (2)S1—C1—C9—N21.1 (3)
O1—S1—N1—C10−46.5 (2)C2—C1—C9—C51.5 (3)
C1—S1—N1—C1068.6 (2)S1—C1—C9—C5−176.59 (18)
O2—S1—C1—C2115.9 (2)C6—C5—C9—N2−0.3 (3)
O1—S1—C1—C2−12.9 (2)C4—C5—C9—N2−179.7 (2)
N1—S1—C1—C2−128.4 (2)C6—C5—C9—C1177.3 (2)
O2—S1—C1—C9−65.9 (2)C4—C5—C9—C1−2.0 (3)
O1—S1—C1—C9165.3 (2)S1—N1—C10—C11−72.1 (3)
N1—S1—C1—C949.7 (2)N1—C10—C11—C16−67.9 (3)
C9—C1—C2—C30.7 (4)N1—C10—C11—C12108.6 (3)
S1—C1—C2—C3178.81 (19)C16—C11—C12—C132.6 (4)
C1—C2—C3—C4−2.4 (4)C10—C11—C12—C13−174.0 (3)
C2—C3—C4—C51.9 (4)C11—C12—C13—C140.8 (4)
C3—C4—C5—C6−179.0 (3)C17—O3—C14—C13−170.0 (3)
C3—C4—C5—C90.3 (4)C17—O3—C14—C1510.0 (4)
C9—C5—C6—C7−1.5 (4)C12—C13—C14—O3176.5 (2)
C4—C5—C6—C7177.8 (3)C12—C13—C14—C15−3.5 (4)
C5—C6—C7—C82.0 (5)O3—C14—C15—C16−177.4 (2)
C9—N2—C8—C7−1.2 (5)C13—C14—C15—C162.6 (4)
C6—C7—C8—N2−0.6 (5)C12—C11—C16—C15−3.5 (4)
C8—N2—C9—C1−176.0 (3)C10—C11—C16—C15173.1 (2)
C8—N2—C9—C51.6 (4)C14—C15—C16—C111.0 (4)
C2—C1—C9—N2179.3 (2)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O2i0.862.413.094 (3)137
C6—H6···O1ii0.932.523.420 (4)162
Symmetry codes: (i) x−1/2, −y+5/2, −z; (ii) x, y−1, z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O2i0.862.413.094 (3)137
C6—H6···O1ii0.932.523.420 (4)162
Symmetry codes: (i) x−1/2, −y+5/2, −z; (ii) x, y−1, z.
Acknowledgements top

The authors thank Professor Dr Hartmut Fueß, Technische Universität Darmstadt, Germany, for diffractometer time.

references
References top

Andrighetti-Fröhner, C. R., Antonio, R. V., Creczynski-Pasa, T. B., Barardi, C. R. & Simões, C. M. O. (2003). Mem. Inst. Oswaldo Cruz, 98, 843–848.

Andrighetti-Fröhner, C. R., da Silva, L. E., Nunes, R. J., Simões, C. M. O. & Foro, S. (2006). Acta Cryst. E62, o3693–o3694.

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Flack, H. D. (1983). Acta Cryst. A39, 876–881.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.

Silva, L. E. da, Andrighetti-Fröhner, C. R., Nunes, R. J., Simões, C. M. O. & Foro, S. (2006). Acta Cryst. E 62, o2104–o2105.

Silva, L. E. da, Joussef, A. C., Pacheco, L. K., Albino, D. B. L., Duarte, A. M. C., Steindel, M. & Rebelo, R. A. (2007). Lett. Drug. Des. Discov. 4, 154–159.

Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13.

Stoe & Cie (1987). REDU4. Version 6.2c. Stoe & Cie GmbH, Darmstadt, Germany.