Download citation
Download citation
link to html
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).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807025706/bh2105sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807025706/bh2105Isup2.hkl
Contains datablock I

CCDC reference: 654848

Key indicators

  • Single-crystal X-ray study
  • T = 299 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.044
  • wR factor = 0.120
  • Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of Tmax/Tmin expected RT(exp) is > 1.10 Absorption corrections should be applied. Tmin and Tmax expected: 0.421 0.491 RT(exp) = 1.166 PLAT057_ALERT_3_C Correction for Absorption Required RT(exp) ... 1.13 PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.65 mm PLAT318_ALERT_2_C Check Hybridisation of N1 in Main Residue . ?
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 66.96 From the CIF: _reflns_number_total 2724 Count of symmetry unique reflns 1599 Completeness (_total/calc) 170.36% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1125 Fraction of Friedel pairs measured 0.704 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

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).

Structure description 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).

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

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
C17H16N2O3SF(000) = 688
Mr = 328.38Dx = 1.427 Mg m3
Orthorhombic, P212121Cu Kα radiation, λ = 1.54180 Å
Hall symbol: P 2ac 2abCell parameters from 25 reflections
a = 7.273 (1) Åθ = 6.4–18.8°
b = 9.146 (1) ŵ = 2.03 mm1
c = 22.975 (3) ÅT = 299 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 = 67.0°, θmin = 3.9°
Graphite monochromatorh = 08
ω/2θ scansk = 1010
3007 measured reflectionsl = 270
2724 independent reflections3 standard reflections every 120 min
2684 reflections with I > 2σ(I) intensity decay: 1.0%
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.044 w = 1/[σ2(Fo2) + (0.08P)2 + 0.3281P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.120(Δ/σ)max = 0.005
S = 1.11Δρmax = 0.37 e Å3
2724 reflectionsΔρmin = 0.26 e Å3
210 parametersExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0078 (8)
Primary atom site location: structure-invariant direct methodsAbsolute structure: (Flack, 1983), 1125 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.02 (2)
Crystal data top
C17H16N2O3SV = 1528.3 (3) Å3
Mr = 328.38Z = 4
Orthorhombic, P212121Cu Kα radiation
a = 7.273 (1) ŵ = 2.03 mm1
b = 9.146 (1) ÅT = 299 K
c = 22.975 (3) Å0.65 × 0.40 × 0.35 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.075
3007 measured reflections3 standard 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 Å3
S = 1.11Δρmin = 0.26 e Å3
2724 reflectionsAbsolute structure: (Flack, 1983), 1125 Friedel pairs
210 parametersAbsolute structure parameter: 0.02 (2)
0 restraints
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)
O30.1936 (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)
H80.16560.90160.03060.074*
C90.3061 (3)0.9891 (3)0.09362 (11)0.0420 (5)
C100.0218 (4)1.3251 (3)0.09868 (14)0.0567 (7)
H10A0.11881.36200.07370.068*
H10B0.00331.39570.12960.068*
C110.0842 (3)1.1829 (3)0.12522 (11)0.0460 (6)
C120.0715 (4)1.1593 (3)0.18508 (12)0.0542 (7)
H120.03481.23520.20940.065*
C130.1128 (4)1.0248 (3)0.20857 (12)0.0560 (7)
H130.10521.01110.24860.067*
C140.1650 (4)0.9106 (3)0.17343 (10)0.0456 (5)
C150.1858 (4)0.9332 (3)0.11396 (10)0.0462 (5)
H150.22580.85780.09000.055*
C160.1462 (4)1.0699 (3)0.09090 (10)0.0465 (5)
H160.16191.08550.05120.056*
C170.2180 (5)0.6546 (4)0.16410 (16)0.0717 (9)
H17A0.33690.65890.14600.086*
H17B0.20910.56730.18710.086*
H17C0.12450.65350.13460.086*
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, º) 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—C10174.4 (2)S1—C1—C9—N21.1 (3)
O1—S1—N1—C1046.5 (2)C2—C1—C9—C51.5 (3)
C1—S1—N1—C1068.6 (2)S1—C1—C9—C5176.59 (18)
O2—S1—C1—C2115.9 (2)C6—C5—C9—N20.3 (3)
O1—S1—C1—C212.9 (2)C4—C5—C9—N2179.7 (2)
N1—S1—C1—C2128.4 (2)C6—C5—C9—C1177.3 (2)
O2—S1—C1—C965.9 (2)C4—C5—C9—C12.0 (3)
O1—S1—C1—C9165.3 (2)S1—N1—C10—C1172.1 (3)
N1—S1—C1—C949.7 (2)N1—C10—C11—C1667.9 (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—C42.4 (4)C10—C11—C12—C13174.0 (3)
C2—C3—C4—C51.9 (4)C11—C12—C13—C140.8 (4)
C3—C4—C5—C6179.0 (3)C17—O3—C14—C13170.0 (3)
C3—C4—C5—C90.3 (4)C17—O3—C14—C1510.0 (4)
C9—C5—C6—C71.5 (4)C12—C13—C14—O3176.5 (2)
C4—C5—C6—C7177.8 (3)C12—C13—C14—C153.5 (4)
C5—C6—C7—C82.0 (5)O3—C14—C15—C16177.4 (2)
C9—N2—C8—C71.2 (5)C13—C14—C15—C162.6 (4)
C6—C7—C8—N20.6 (5)C12—C11—C16—C153.5 (4)
C8—N2—C9—C1176.0 (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, º) 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) x1/2, y+5/2, z; (ii) x, y1, z.

Experimental details

Crystal data
Chemical formulaC17H16N2O3S
Mr328.38
Crystal system, space groupOrthorhombic, P212121
Temperature (K)299
a, b, c (Å)7.273 (1), 9.146 (1), 22.975 (3)
V3)1528.3 (3)
Z4
Radiation typeCu Kα
µ (mm1)2.03
Crystal size (mm)0.65 × 0.40 × 0.35
Data collection
DiffractometerEnraf–Nonius CAD-4
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
3007, 2724, 2684
Rint0.075
(sin θ/λ)max1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.120, 1.11
No. of reflections2724
No. of parameters210
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.37, 0.26
Absolute structure(Flack, 1983), 1125 Friedel pairs
Absolute structure parameter0.02 (2)

Computer programs: CAD-4-PC Software (Enraf–Nonius, 1996), CAD-4-PC Software, REDU4 (Stoe & Cie, 1987), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O2i0.862.413.094 (3)137.0
C6—H6···O1ii0.932.523.420 (4)161.8
Symmetry codes: (i) x1/2, y+5/2, z; (ii) x, y1, z.
 

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