Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807025706/bh2105sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807025706/bh2105Isup2.hkl |
CCDC reference: 654848
Key indicators
- Single-crystal X-ray study
- T = 299 K
- Mean (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
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).
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).
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).
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.
C17H16N2O3S | F(000) = 688 |
Mr = 328.38 | Dx = 1.427 Mg m−3 |
Orthorhombic, P212121 | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 25 reflections |
a = 7.273 (1) Å | θ = 6.4–18.8° |
b = 9.146 (1) Å | µ = 2.03 mm−1 |
c = 22.975 (3) Å | T = 299 K |
V = 1528.3 (3) Å3 | Prism, colourless |
Z = 4 | 0.65 × 0.40 × 0.35 mm |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.075 |
Radiation source: fine-focus sealed tube | θmax = 67.0°, θmin = 3.9° |
Graphite monochromator | h = 0→8 |
ω/2θ scans | k = −10→10 |
3007 measured reflections | l = −27→0 |
2724 independent reflections | 3 standard reflections every 120 min |
2684 reflections with I > 2σ(I) | intensity decay: 1.0% |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-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 = 1.11 | Δρmax = 0.37 e Å−3 |
2724 reflections | Δρmin = −0.26 e Å−3 |
210 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0078 (8) |
Primary atom site location: structure-invariant direct methods | Absolute structure: (Flack, 1983), 1125 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.02 (2) |
C17H16N2O3S | V = 1528.3 (3) Å3 |
Mr = 328.38 | Z = 4 |
Orthorhombic, P212121 | Cu Kα radiation |
a = 7.273 (1) Å | µ = 2.03 mm−1 |
b = 9.146 (1) Å | T = 299 K |
c = 22.975 (3) Å | 0.65 × 0.40 × 0.35 mm |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.075 |
3007 measured reflections | 3 standard reflections every 120 min |
2724 independent reflections | intensity decay: 1.0% |
2684 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.120 | Δρmax = 0.37 e Å−3 |
S = 1.11 | Δρmin = −0.26 e Å−3 |
2724 reflections | Absolute structure: (Flack, 1983), 1125 Friedel pairs |
210 parameters | Absolute structure parameter: 0.02 (2) |
0 restraints |
x | y | z | Uiso*/Ueq | ||
S1 | 0.34694 (9) | 1.29117 (6) | 0.09586 (3) | 0.0453 (2) | |
O1 | 0.3555 (3) | 1.3926 (2) | 0.14329 (9) | 0.0636 (5) | |
O2 | 0.4836 (3) | 1.2999 (2) | 0.05121 (9) | 0.0628 (5) | |
O3 | −0.1936 (3) | 0.7783 (2) | 0.20022 (8) | 0.0627 (5) | |
N1 | 0.1504 (3) | 1.3143 (2) | 0.06407 (9) | 0.0488 (5) | |
H1N | 0.1455 | 1.3204 | 0.0267 | 0.059* | |
N2 | 0.2562 (3) | 1.0071 (3) | 0.03640 (9) | 0.0502 (5) | |
C1 | 0.3545 (3) | 1.1131 (3) | 0.12712 (10) | 0.0410 (5) | |
C2 | 0.4028 (4) | 1.1002 (3) | 0.18424 (11) | 0.0487 (6) | |
H2 | 0.4329 | 1.1831 | 0.2057 | 0.058* | |
C3 | 0.4070 (4) | 0.9610 (4) | 0.21093 (13) | 0.0572 (7) | |
H3 | 0.4444 | 0.9521 | 0.2495 | 0.069* | |
C4 | 0.3568 (4) | 0.8407 (3) | 0.18066 (13) | 0.0566 (7) | |
H4 | 0.3566 | 0.7501 | 0.1990 | 0.068* | |
C5 | 0.3044 (4) | 0.8507 (3) | 0.12124 (12) | 0.0490 (6) | |
C6 | 0.2484 (4) | 0.7293 (3) | 0.08807 (15) | 0.0636 (8) | |
H6 | 0.2483 | 0.6363 | 0.1045 | 0.076* | |
C7 | 0.1941 (5) | 0.7485 (4) | 0.03161 (16) | 0.0699 (9) | |
H7 | 0.1531 | 0.6699 | 0.0094 | 0.084* | |
C8 | 0.2017 (5) | 0.8899 (4) | 0.00795 (13) | 0.0621 (8) | |
H8 | 0.1656 | 0.9016 | −0.0306 | 0.074* | |
C9 | 0.3061 (3) | 0.9891 (3) | 0.09362 (11) | 0.0420 (5) | |
C10 | −0.0218 (4) | 1.3251 (3) | 0.09868 (14) | 0.0567 (7) | |
H10A | −0.1188 | 1.3620 | 0.0737 | 0.068* | |
H10B | −0.0033 | 1.3957 | 0.1296 | 0.068* | |
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 | −0.0348 | 1.2352 | 0.2094 | 0.065* | |
C13 | −0.1128 (4) | 1.0248 (3) | 0.20857 (12) | 0.0560 (7) | |
H13 | −0.1052 | 1.0111 | 0.2486 | 0.067* | |
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 | −0.2258 | 0.8578 | 0.0900 | 0.055* | |
C16 | −0.1462 (4) | 1.0699 (3) | 0.09090 (10) | 0.0465 (5) | |
H16 | −0.1619 | 1.0855 | 0.0512 | 0.056* | |
C17 | −0.2180 (5) | 0.6546 (4) | 0.16410 (16) | 0.0717 (9) | |
H17A | −0.3369 | 0.6589 | 0.1460 | 0.086* | |
H17B | −0.2091 | 0.5673 | 0.1871 | 0.086* | |
H17C | −0.1245 | 0.6535 | 0.1346 | 0.086* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0539 (4) | 0.0362 (3) | 0.0458 (3) | −0.0037 (3) | −0.0012 (3) | 0.0070 (2) |
O1 | 0.0878 (15) | 0.0416 (10) | 0.0613 (11) | −0.0064 (11) | −0.0133 (11) | −0.0026 (8) |
O2 | 0.0623 (11) | 0.0649 (12) | 0.0612 (11) | −0.0104 (10) | 0.0108 (9) | 0.0205 (10) |
O3 | 0.0722 (13) | 0.0613 (11) | 0.0545 (10) | 0.0062 (10) | 0.0053 (9) | 0.0184 (9) |
N1 | 0.0593 (12) | 0.0399 (10) | 0.0471 (10) | 0.0027 (10) | −0.0036 (10) | 0.0098 (8) |
N2 | 0.0598 (13) | 0.0480 (12) | 0.0426 (10) | 0.0022 (10) | 0.0044 (9) | 0.0007 (9) |
C1 | 0.0408 (11) | 0.0381 (11) | 0.0440 (11) | 0.0049 (10) | 0.0022 (10) | 0.0096 (9) |
C2 | 0.0471 (13) | 0.0534 (15) | 0.0457 (13) | 0.0060 (11) | −0.0006 (10) | 0.0025 (12) |
C3 | 0.0506 (15) | 0.0715 (19) | 0.0495 (14) | 0.0168 (13) | 0.0037 (11) | 0.0238 (14) |
C4 | 0.0497 (14) | 0.0528 (14) | 0.0672 (16) | 0.0138 (12) | 0.0106 (13) | 0.0261 (13) |
C5 | 0.0430 (12) | 0.0403 (12) | 0.0637 (15) | 0.0098 (10) | 0.0120 (11) | 0.0102 (11) |
C6 | 0.0596 (15) | 0.0393 (14) | 0.092 (2) | 0.0055 (12) | 0.0213 (16) | 0.0064 (14) |
C7 | 0.076 (2) | 0.0494 (16) | 0.084 (2) | −0.0050 (14) | 0.0171 (17) | −0.0196 (15) |
C8 | 0.076 (2) | 0.0584 (17) | 0.0515 (14) | −0.0013 (15) | 0.0080 (13) | −0.0115 (13) |
C9 | 0.0396 (11) | 0.0395 (11) | 0.0469 (12) | 0.0075 (9) | 0.0065 (9) | 0.0055 (10) |
C10 | 0.0557 (14) | 0.0413 (13) | 0.0730 (18) | 0.0112 (12) | −0.0013 (14) | 0.0025 (13) |
C11 | 0.0411 (11) | 0.0440 (14) | 0.0529 (13) | 0.0090 (10) | 0.0003 (10) | −0.0015 (11) |
C12 | 0.0536 (14) | 0.0598 (16) | 0.0492 (13) | 0.0054 (12) | −0.0021 (12) | −0.0154 (12) |
C13 | 0.0561 (15) | 0.0736 (18) | 0.0385 (12) | 0.0050 (13) | −0.0034 (11) | 0.0015 (13) |
C14 | 0.0420 (12) | 0.0523 (13) | 0.0427 (12) | 0.0074 (11) | 0.0026 (10) | 0.0076 (10) |
C15 | 0.0503 (13) | 0.0480 (13) | 0.0401 (11) | 0.0000 (11) | −0.0020 (10) | −0.0010 (10) |
C16 | 0.0511 (13) | 0.0517 (13) | 0.0367 (11) | 0.0036 (11) | −0.0034 (11) | 0.0047 (10) |
C17 | 0.083 (2) | 0.0505 (16) | 0.081 (2) | 0.0083 (15) | 0.0259 (18) | 0.0121 (15) |
S1—O2 | 1.431 (2) | C6—H6 | 0.9300 |
S1—O1 | 1.433 (2) | C7—C8 | 1.403 (5) |
S1—N1 | 1.619 (2) | C7—H7 | 0.9300 |
S1—C1 | 1.781 (2) | C8—H8 | 0.9300 |
O3—C14 | 1.373 (3) | C10—C11 | 1.506 (4) |
O3—C17 | 1.415 (4) | C10—H10A | 0.9700 |
N1—C10 | 1.486 (4) | C10—H10B | 0.9700 |
N1—H1N | 0.8600 | C11—C16 | 1.376 (4) |
N2—C8 | 1.317 (4) | C11—C12 | 1.395 (4) |
N2—C9 | 1.374 (3) | C12—C13 | 1.377 (4) |
C1—C2 | 1.364 (3) | C12—H12 | 0.9300 |
C1—C9 | 1.415 (3) | C13—C14 | 1.374 (4) |
C2—C3 | 1.414 (4) | C13—H13 | 0.9300 |
C2—H2 | 0.9300 | C14—C15 | 1.390 (3) |
C3—C4 | 1.352 (5) | C15—C16 | 1.388 (4) |
C3—H3 | 0.9300 | C15—H15 | 0.9300 |
C4—C5 | 1.420 (4) | C16—H16 | 0.9300 |
C4—H4 | 0.9300 | C17—H17A | 0.9600 |
C5—C6 | 1.407 (4) | C17—H17B | 0.9600 |
C5—C9 | 1.416 (3) | C17—H17C | 0.9600 |
C6—C7 | 1.367 (5) | ||
O2—S1—O1 | 118.60 (14) | C7—C8—H8 | 117.6 |
O2—S1—N1 | 106.43 (12) | N2—C9—C1 | 119.3 (2) |
O1—S1—N1 | 107.28 (13) | N2—C9—C5 | 122.3 (2) |
O2—S1—C1 | 108.61 (12) | C1—C9—C5 | 118.3 (2) |
O1—S1—C1 | 106.51 (11) | N1—C10—C11 | 114.4 (2) |
N1—S1—C1 | 109.18 (11) | N1—C10—H10A | 108.7 |
C14—O3—C17 | 117.4 (2) | C11—C10—H10A | 108.7 |
C10—N1—S1 | 120.73 (18) | N1—C10—H10B | 108.7 |
C10—N1—H1N | 119.6 | C11—C10—H10B | 108.7 |
S1—N1—H1N | 119.6 | H10A—C10—H10B | 107.6 |
C8—N2—C9 | 117.2 (2) | C16—C11—C12 | 118.0 (2) |
C2—C1—C9 | 121.2 (2) | C16—C11—C10 | 121.0 (2) |
C2—C1—S1 | 118.4 (2) | C12—C11—C10 | 120.8 (3) |
C9—C1—S1 | 120.40 (17) | C13—C12—C11 | 120.7 (3) |
C1—C2—C3 | 120.1 (3) | C13—C12—H12 | 119.7 |
C1—C2—H2 | 120.0 | C11—C12—H12 | 119.7 |
C3—C2—H2 | 120.0 | C14—C13—C12 | 120.6 (2) |
C4—C3—C2 | 120.3 (2) | C14—C13—H13 | 119.7 |
C4—C3—H3 | 119.9 | C12—C13—H13 | 119.7 |
C2—C3—H3 | 119.9 | O3—C14—C13 | 116.6 (2) |
C3—C4—C5 | 121.0 (2) | O3—C14—C15 | 123.7 (2) |
C3—C4—H4 | 119.5 | C13—C14—C15 | 119.6 (2) |
C5—C4—H4 | 119.5 | C16—C15—C14 | 119.1 (2) |
C6—C5—C9 | 117.7 (3) | C16—C15—H15 | 120.4 |
C6—C5—C4 | 123.2 (3) | C14—C15—H15 | 120.4 |
C9—C5—C4 | 119.1 (3) | C11—C16—C15 | 121.7 (2) |
C7—C6—C5 | 119.7 (3) | C11—C16—H16 | 119.1 |
C7—C6—H6 | 120.1 | C15—C16—H16 | 119.1 |
C5—C6—H6 | 120.1 | O3—C17—H17A | 109.5 |
C6—C7—C8 | 118.3 (3) | O3—C17—H17B | 109.5 |
C6—C7—H7 | 120.8 | H17A—C17—H17B | 109.5 |
C8—C7—H7 | 120.8 | O3—C17—H17C | 109.5 |
N2—C8—C7 | 124.7 (3) | H17A—C17—H17C | 109.5 |
N2—C8—H8 | 117.6 | H17B—C17—H17C | 109.5 |
O2—S1—N1—C10 | −174.4 (2) | S1—C1—C9—N2 | 1.1 (3) |
O1—S1—N1—C10 | −46.5 (2) | C2—C1—C9—C5 | 1.5 (3) |
C1—S1—N1—C10 | 68.6 (2) | S1—C1—C9—C5 | −176.59 (18) |
O2—S1—C1—C2 | 115.9 (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—C1 | 177.3 (2) |
O2—S1—C1—C9 | −65.9 (2) | C4—C5—C9—C1 | −2.0 (3) |
O1—S1—C1—C9 | 165.3 (2) | S1—N1—C10—C11 | −72.1 (3) |
N1—S1—C1—C9 | 49.7 (2) | N1—C10—C11—C16 | −67.9 (3) |
C9—C1—C2—C3 | 0.7 (4) | N1—C10—C11—C12 | 108.6 (3) |
S1—C1—C2—C3 | 178.81 (19) | C16—C11—C12—C13 | 2.6 (4) |
C1—C2—C3—C4 | −2.4 (4) | C10—C11—C12—C13 | −174.0 (3) |
C2—C3—C4—C5 | 1.9 (4) | C11—C12—C13—C14 | 0.8 (4) |
C3—C4—C5—C6 | −179.0 (3) | C17—O3—C14—C13 | −170.0 (3) |
C3—C4—C5—C9 | 0.3 (4) | C17—O3—C14—C15 | 10.0 (4) |
C9—C5—C6—C7 | −1.5 (4) | C12—C13—C14—O3 | 176.5 (2) |
C4—C5—C6—C7 | 177.8 (3) | C12—C13—C14—C15 | −3.5 (4) |
C5—C6—C7—C8 | 2.0 (5) | O3—C14—C15—C16 | −177.4 (2) |
C9—N2—C8—C7 | −1.2 (5) | C13—C14—C15—C16 | 2.6 (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—C15 | 173.1 (2) |
C8—N2—C9—C5 | 1.6 (4) | C14—C15—C16—C11 | 1.0 (4) |
C2—C1—C9—N2 | 179.3 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2i | 0.86 | 2.41 | 3.094 (3) | 137 |
C6—H6···O1ii | 0.93 | 2.52 | 3.420 (4) | 162 |
Symmetry codes: (i) x−1/2, −y+5/2, −z; (ii) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C17H16N2O3S |
Mr | 328.38 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 299 |
a, b, c (Å) | 7.273 (1), 9.146 (1), 22.975 (3) |
V (Å3) | 1528.3 (3) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 2.03 |
Crystal size (mm) | 0.65 × 0.40 × 0.35 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3007, 2724, 2684 |
Rint | 0.075 |
(sin θ/λ)max (Å−1) | 0.597 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.120, 1.11 |
No. of reflections | 2724 |
No. of parameters | 210 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.37, −0.26 |
Absolute structure | (Flack, 1983), 1125 Friedel pairs |
Absolute structure parameter | 0.02 (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.
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O2i | 0.86 | 2.41 | 3.094 (3) | 137.0 |
C6—H6···O1ii | 0.93 | 2.52 | 3.420 (4) | 161.8 |
Symmetry codes: (i) x−1/2, −y+5/2, −z; (ii) x, y−1, z. |
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).