Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807029303/bh2110sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807029303/bh2110Isup2.hkl |
CCDC reference: 655603
Key indicators
- Single-crystal X-ray study
- T = 293 K
- R factor = 0.047
- wR factor = 0.135
- Data-to-parameter ratio = 13.1
checkCIF/PLATON results
No syntax errors found No errors found in this datablock
Compound (I) was synthesized according to the method of Cremlyn et al. (1984). 4-methoxychalcone (6.63 g, 27.87 mmol), was reacted with chlorosulphonic acid (19.48 g, 167.2 mmol) at room temperature for 1 week. The red solution was poured onto crushed ice with stirring to give the sulfonyl chloride as a yellow solid. The sulfonyl chloride (0.50 g, 1.48 mmol) was treated with benzylamine (0.23 g, 2.19 mmol) in methanol at 273 K. The mixture was reacted at room temperature for 1 h and was then poured onto ice-water. The precipitate was collected by filtration, washed with cold methanol, dried and recrystallized in hot ethanol (yield 0.25 g, 42%). M.p. 167–170°C (yellow crystalline solid). Colourless single crystals suitable for X-ray analysis were obtained by slow evaporation of a chloroform solution. 1H NMR (CDCl3): δ: 3.89 (s, 3H, OCH3), 4.17 (d, J=6.19 Hz, 2H, CH2), 6.92–8.28 (m, 13H, ArH, 2H olefinic H). Elemental Analysis calculated for C23H21NO4S: C 67.79, H 5.19, N 3.44, S 7.87%; Found: C 67.52, H 5.11, N 3.50, S 7.62%.
All non-H atoms were refined with anisotropic displacement parameters. H atoms attached to C atoms were added at their calculated positions and included in the refinement, with constrained distances C—H = 0.96 (CH3), 0.97 (CH2) or 0.93 Å (CHAr), and Uiso(H) = 1.2Ueq(carrier C) or 1.5Ueq(C102) for the methyl group. Atom H1 bonded to N1 was found in a difference map and treated as an isotropic free atom.
Sulfonamide is a pharmacophoric group of over than 30 pharmaceuticals which are in clinical use, with antibacterial, diuretic, oral antidiabetic, HIV protease inhibitory (Supuran et al., 2003) and antimalarial (Petersen, 2004) activities. Many novel sulfonamide derivatives have recently been reported to show carbonic anhydrase inhibitory action, matrix metalloproteinase inhibitory action, endothelin receptor antagonism, antitumoral (Supuran et al., 2003) and antileishmanial (Bhattacharya et al., 2004) activities.
Naturally occurring and synthetic chalcones are known to have a wide range of potential pharmacological activities, such as anti-inflammatory, antibacterial, anticancer, antiviral, antimalarial (Ni et al., 2004), antitrypanosomal, antileishmanial (Lunardi et al., 2003) and nitric oxide inhibitory action (Rojas et al., 2002). A combination of two or more pharmacophoric groups can enhance the discovery probability of new lead compounds, specially if closely related activities are involved. Recently, analogs of sulfonamide chalcone derivatives were synthesized and showed activity against cultured Plasmodium falciparum parasites (Dominguez et al., 2005). In order to investigate of bioactivity of the combined compounds, we have prepared some sulfonamide chalcone derivatives, and in this paper we present the synthesis and X-ray study of (I).
The molecule of (I) shows an angular geometry (Fig. 1) resulting from the structural combination of sulfonamide and chalcone moieties, with the vertices of the molecule occupied by S atom. The chalcone arm is quasi planar, where the dihedral angles between the best planes of the rings C9···C14 and C18···C23 is 10.85 (6)° and the best plane of the central chain C13—C15═ C16—C17 with respect to phenyl rings C9···C14 and C18···C23 are 10.4 (1)° and 11.6 (1)°, respectively. This feature suggests that there is electronic delocalization forming an extended π -electron conjugated system in this moiety. It is in accord with decreased length of the C16—C17 [1.471 (3) Å] single bond and the increased length of the C15═C16 [1.322 (4) Å] double bond. In addition, the methoxy group is also almost coplanar with its attached phenyl ring. It was observed in similar structures of chalcone (Subbiah Pandi et al., 2003 and cited references) when the mehtoxy is in para position with respect to the central chain. In the sulfonamide moiety, the distances and angles around N1 and C2 are within the expected range found in similar structures searched in CSD V5.28 with Mogul (Bruno et al., 2004). The phenyl ring C3···C8 is almost perpendicular to the mean plane of the chalcone arm, where the dihedral angle between these planes is 85.04 (8)°. An intermolecular hydrogen bond [N1—H1···O171i, NH = 0.84 (3) Å, H···O = 2.23 (3) Å, N—H···O = 156 (3)°, symmetry code: (i) x, y, z - 1] promotes a zigzag infinite chain formation running parallel to the crystallographic [001] axis (Fig. 2), keeping the molecules stacked in this direction.
For related literature, see: Bhattacharya et al. (2004); Cremlyn et al. (1984); Dominguez et al. (2005); Lunardi et al. (2003); Ni et al. (2004); Subbiah Pandi et al. (2003); Petersen (2004); Rojas et al. (2002); Supuran et al. (2003); Bruno et al. (2004).
Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: HELENA (Spek, 1996); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97.
C23H21NO4S | F(000) = 428 |
Mr = 407.47 | Dx = 1.379 Mg m−3 |
Triclinic, P1 | Melting point = 440–443 K |
a = 10.3671 (12) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.3750 (8) Å | Cell parameters from 25 reflections |
c = 10.7977 (14) Å | θ = 6.7–15.4° |
α = 84.88 (1)° | µ = 0.20 mm−1 |
β = 68.79 (1)° | T = 293 K |
γ = 65.40 (1)° | Irregular block, colourless |
V = 981.9 (2) Å3 | 0.50 × 0.33 × 0.13 mm |
Z = 2 |
Enraf-Nonius CAD-4 diffractometer | 2573 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.027 |
Graphite monochromator | θmax = 25.1°, θmin = 2.0° |
ω–2θ scans | h = −12→11 |
Absorption correction: ψ scan (PLATON; Spek, 2003; North et al., 1968) | k = −12→12 |
Tmin = 0.924, Tmax = 0.969 | l = −12→0 |
3694 measured reflections | 3 standard reflections every 200 reflections |
3490 independent reflections | intensity decay: <1% |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.135 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.067P)2 + 0.4657P] where P = (Fo2 + 2Fc2)/3 |
3490 reflections | (Δ/σ)max < 0.001 |
266 parameters | Δρmax = 0.35 e Å−3 |
0 restraints | Δρmin = −0.47 e Å−3 |
C23H21NO4S | γ = 65.40 (1)° |
Mr = 407.47 | V = 981.9 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.3671 (12) Å | Mo Kα radiation |
b = 10.3750 (8) Å | µ = 0.20 mm−1 |
c = 10.7977 (14) Å | T = 293 K |
α = 84.88 (1)° | 0.50 × 0.33 × 0.13 mm |
β = 68.79 (1)° |
Enraf-Nonius CAD-4 diffractometer | 2573 reflections with I > 2σ(I) |
Absorption correction: ψ scan (PLATON; Spek, 2003; North et al., 1968) | Rint = 0.027 |
Tmin = 0.924, Tmax = 0.969 | 3 standard reflections every 200 reflections |
3694 measured reflections | intensity decay: <1% |
3490 independent reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.135 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.35 e Å−3 |
3490 reflections | Δρmin = −0.47 e Å−3 |
266 parameters |
x | y | z | Uiso*/Ueq | ||
S1 | 0.28300 (8) | 0.31669 (7) | 0.78462 (6) | 0.0353 (2) | |
O1 | 0.2332 (2) | 0.43617 (19) | 0.87332 (18) | 0.0461 (5) | |
O2 | 0.4138 (2) | 0.2877 (2) | 0.66670 (18) | 0.0484 (5) | |
N1 | 0.1427 (3) | 0.3383 (2) | 0.7393 (2) | 0.0367 (5) | |
H1 | 0.170 (3) | 0.275 (3) | 0.681 (3) | 0.044 (8)* | |
C2 | −0.0055 (3) | 0.3700 (3) | 0.8446 (3) | 0.0480 (7) | |
H2A | −0.0265 | 0.4446 | 0.9066 | 0.058* | |
H2B | −0.0014 | 0.2859 | 0.8932 | 0.058* | |
C3 | −0.1333 (3) | 0.4163 (3) | 0.7925 (3) | 0.0420 (7) | |
C4 | −0.2592 (4) | 0.3912 (4) | 0.8631 (3) | 0.0589 (9) | |
H4 | −0.2633 | 0.3450 | 0.9414 | 0.071* | |
C5 | −0.3807 (4) | 0.4334 (4) | 0.8197 (4) | 0.0693 (10) | |
H5 | −0.4656 | 0.4162 | 0.8689 | 0.083* | |
C6 | −0.3745 (4) | 0.5010 (4) | 0.7030 (4) | 0.0654 (10) | |
H6 | −0.4545 | 0.5281 | 0.6723 | 0.079* | |
C7 | −0.2501 (4) | 0.5281 (3) | 0.6327 (3) | 0.0604 (9) | |
H7 | −0.2466 | 0.5752 | 0.5549 | 0.073* | |
C8 | −0.1298 (4) | 0.4863 (3) | 0.6762 (3) | 0.0489 (7) | |
H8 | −0.0458 | 0.5050 | 0.6273 | 0.059* | |
C9 | 0.3096 (3) | 0.1678 (3) | 0.8821 (2) | 0.0315 (6) | |
C10 | 0.3649 (3) | 0.0305 (3) | 0.8251 (2) | 0.0325 (6) | |
C11 | 0.3815 (3) | −0.0826 (3) | 0.9063 (3) | 0.0380 (6) | |
H11 | 0.4192 | −0.1747 | 0.8698 | 0.046* | |
C12 | 0.3421 (3) | −0.0579 (3) | 1.0408 (3) | 0.0381 (6) | |
H12 | 0.3534 | −0.1347 | 1.0939 | 0.046* | |
C13 | 0.2860 (3) | 0.0776 (3) | 1.1006 (2) | 0.0345 (6) | |
C14 | 0.2715 (3) | 0.1896 (3) | 1.0186 (2) | 0.0331 (6) | |
H14 | 0.2355 | 0.2812 | 1.0555 | 0.040* | |
C15 | 0.2394 (3) | 0.1059 (3) | 1.2440 (2) | 0.0376 (6) | |
H15 | 0.2134 | 0.1980 | 1.2734 | 0.045* | |
C16 | 0.2302 (3) | 0.0138 (3) | 1.3362 (2) | 0.0393 (6) | |
H16 | 0.2576 | −0.0800 | 1.3102 | 0.047* | |
C17 | 0.1780 (3) | 0.0552 (3) | 1.4786 (2) | 0.0362 (6) | |
C18 | 0.1533 (3) | −0.0500 (3) | 1.5782 (2) | 0.0348 (6) | |
C19 | 0.2058 (4) | −0.1925 (3) | 1.5438 (3) | 0.0468 (7) | |
H19 | 0.2517 | −0.2255 | 1.4545 | 0.056* | |
C20 | 0.1905 (4) | −0.2867 (3) | 1.6415 (3) | 0.0562 (9) | |
H20 | 0.2259 | −0.3828 | 1.6177 | 0.067* | |
C21 | 0.1231 (4) | −0.2384 (3) | 1.7735 (3) | 0.0519 (8) | |
H21 | 0.1144 | −0.3020 | 1.8391 | 0.062* | |
C22 | 0.0689 (3) | −0.0973 (3) | 1.8085 (3) | 0.0477 (7) | |
H22 | 0.0222 | −0.0648 | 1.8980 | 0.057* | |
C23 | 0.0829 (3) | −0.0028 (3) | 1.7121 (3) | 0.0407 (6) | |
H23 | 0.0449 | 0.0934 | 1.7367 | 0.049* | |
C102 | 0.4726 (3) | −0.1232 (3) | 0.6292 (3) | 0.0449 (7) | |
H10A | 0.4882 | −0.1177 | 0.5360 | 0.067* | |
H10B | 0.4116 | −0.1753 | 0.6687 | 0.067* | |
H10C | 0.5691 | −0.1708 | 0.6402 | 0.067* | |
O101 | 0.3966 (2) | 0.01728 (18) | 0.69291 (16) | 0.0388 (5) | |
O171 | 0.1559 (3) | 0.1728 (2) | 1.51546 (18) | 0.0480 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0476 (4) | 0.0353 (4) | 0.0232 (3) | −0.0175 (3) | −0.0134 (3) | 0.0062 (2) |
O1 | 0.0728 (14) | 0.0373 (10) | 0.0336 (10) | −0.0245 (10) | −0.0239 (10) | 0.0065 (8) |
O2 | 0.0534 (13) | 0.0578 (12) | 0.0324 (11) | −0.0282 (10) | −0.0082 (9) | 0.0077 (9) |
N1 | 0.0428 (13) | 0.0399 (12) | 0.0222 (11) | −0.0095 (10) | −0.0143 (10) | 0.0004 (9) |
C2 | 0.0459 (17) | 0.0610 (19) | 0.0276 (14) | −0.0138 (14) | −0.0123 (13) | 0.0011 (13) |
C3 | 0.0463 (17) | 0.0397 (15) | 0.0357 (15) | −0.0113 (13) | −0.0170 (13) | −0.0008 (12) |
C4 | 0.062 (2) | 0.065 (2) | 0.052 (2) | −0.0281 (18) | −0.0229 (17) | 0.0136 (16) |
C5 | 0.054 (2) | 0.068 (2) | 0.089 (3) | −0.0280 (18) | −0.026 (2) | 0.008 (2) |
C6 | 0.062 (2) | 0.058 (2) | 0.079 (3) | −0.0098 (17) | −0.044 (2) | −0.0065 (18) |
C7 | 0.064 (2) | 0.058 (2) | 0.054 (2) | −0.0100 (17) | −0.0330 (18) | 0.0060 (15) |
C8 | 0.0480 (18) | 0.0538 (18) | 0.0383 (16) | −0.0127 (14) | −0.0186 (14) | 0.0050 (13) |
C9 | 0.0362 (14) | 0.0368 (13) | 0.0234 (12) | −0.0145 (11) | −0.0143 (11) | 0.0066 (10) |
C10 | 0.0336 (14) | 0.0394 (14) | 0.0244 (13) | −0.0138 (11) | −0.0120 (11) | 0.0036 (10) |
C11 | 0.0499 (17) | 0.0345 (14) | 0.0293 (14) | −0.0155 (12) | −0.0166 (12) | 0.0043 (11) |
C12 | 0.0494 (16) | 0.0380 (14) | 0.0289 (14) | −0.0186 (13) | −0.0179 (12) | 0.0115 (11) |
C13 | 0.0379 (15) | 0.0429 (14) | 0.0255 (13) | −0.0189 (12) | −0.0130 (11) | 0.0072 (11) |
C14 | 0.0394 (15) | 0.0345 (13) | 0.0252 (13) | −0.0138 (11) | −0.0133 (11) | 0.0026 (10) |
C15 | 0.0459 (16) | 0.0452 (15) | 0.0260 (13) | −0.0200 (13) | −0.0167 (12) | 0.0047 (11) |
C16 | 0.0535 (17) | 0.0423 (15) | 0.0241 (13) | −0.0208 (13) | −0.0157 (12) | 0.0054 (11) |
C17 | 0.0444 (16) | 0.0420 (15) | 0.0262 (13) | −0.0195 (13) | −0.0159 (12) | 0.0057 (11) |
C18 | 0.0384 (15) | 0.0445 (15) | 0.0243 (13) | −0.0179 (12) | −0.0138 (11) | 0.0045 (11) |
C19 | 0.065 (2) | 0.0474 (16) | 0.0289 (15) | −0.0258 (15) | −0.0159 (14) | 0.0046 (12) |
C20 | 0.082 (2) | 0.0429 (17) | 0.0404 (17) | −0.0256 (16) | −0.0196 (17) | 0.0082 (13) |
C21 | 0.067 (2) | 0.0583 (19) | 0.0350 (16) | −0.0330 (17) | −0.0186 (15) | 0.0178 (14) |
C22 | 0.0548 (19) | 0.065 (2) | 0.0235 (14) | −0.0287 (16) | −0.0106 (13) | 0.0070 (13) |
C23 | 0.0480 (17) | 0.0463 (16) | 0.0287 (14) | −0.0208 (13) | −0.0130 (13) | 0.0023 (11) |
C102 | 0.0517 (18) | 0.0476 (16) | 0.0296 (14) | −0.0157 (14) | −0.0125 (13) | −0.0044 (12) |
O101 | 0.0537 (12) | 0.0380 (10) | 0.0212 (9) | −0.0140 (9) | −0.0151 (8) | 0.0005 (7) |
O171 | 0.0739 (14) | 0.0467 (12) | 0.0284 (10) | −0.0295 (10) | −0.0194 (10) | 0.0076 (8) |
S1—O2 | 1.425 (2) | C12—C13 | 1.392 (4) |
S1—O1 | 1.4280 (19) | C12—H12 | 0.9300 |
S1—N1 | 1.621 (2) | C13—C14 | 1.386 (3) |
S1—C9 | 1.770 (2) | C13—C15 | 1.462 (3) |
N1—C2 | 1.464 (4) | C14—H14 | 0.9300 |
N1—H1 | 0.84 (3) | C15—C16 | 1.322 (4) |
C2—C3 | 1.505 (4) | C15—H15 | 0.9300 |
C2—H2A | 0.9700 | C16—C17 | 1.471 (3) |
C2—H2B | 0.9700 | C16—H16 | 0.9300 |
C3—C4 | 1.371 (4) | C17—O171 | 1.219 (3) |
C3—C8 | 1.390 (4) | C17—C18 | 1.496 (4) |
C4—C5 | 1.389 (5) | C18—C19 | 1.378 (4) |
C4—H4 | 0.9300 | C18—C23 | 1.388 (3) |
C5—C6 | 1.380 (5) | C19—C20 | 1.384 (4) |
C5—H5 | 0.9300 | C19—H19 | 0.9300 |
C6—C7 | 1.369 (5) | C20—C21 | 1.374 (4) |
C6—H6 | 0.9300 | C20—H20 | 0.9300 |
C7—C8 | 1.378 (4) | C21—C22 | 1.364 (4) |
C7—H7 | 0.9300 | C21—H21 | 0.9300 |
C8—H8 | 0.9300 | C22—C23 | 1.375 (4) |
C9—C14 | 1.394 (3) | C22—H22 | 0.9300 |
C9—C10 | 1.398 (3) | C23—H23 | 0.9300 |
C10—O101 | 1.350 (3) | C102—O101 | 1.430 (3) |
C10—C11 | 1.390 (3) | C102—H10A | 0.9600 |
C11—C12 | 1.376 (4) | C102—H10B | 0.9600 |
C11—H11 | 0.9300 | C102—H10C | 0.9600 |
O2—S1—O1 | 119.04 (12) | C11—C12—H12 | 118.7 |
O2—S1—N1 | 107.38 (12) | C13—C12—H12 | 118.7 |
O1—S1—N1 | 107.21 (12) | C14—C13—C12 | 117.3 (2) |
O2—S1—C9 | 110.21 (12) | C14—C13—C15 | 119.6 (2) |
O1—S1—C9 | 105.83 (11) | C12—C13—C15 | 123.0 (2) |
N1—S1—C9 | 106.50 (12) | C13—C14—C9 | 121.4 (2) |
C2—N1—S1 | 117.40 (18) | C13—C14—H14 | 119.3 |
C2—N1—H1 | 115 (2) | C9—C14—H14 | 119.3 |
S1—N1—H1 | 110 (2) | C16—C15—C13 | 126.7 (3) |
N1—C2—C3 | 113.2 (2) | C16—C15—H15 | 116.7 |
N1—C2—H2A | 108.9 | C13—C15—H15 | 116.7 |
C3—C2—H2A | 108.9 | C15—C16—C17 | 121.9 (3) |
N1—C2—H2B | 108.9 | C15—C16—H16 | 119.0 |
C3—C2—H2B | 108.9 | C17—C16—H16 | 119.0 |
H2A—C2—H2B | 107.8 | O171—C17—C16 | 120.9 (2) |
C4—C3—C8 | 118.5 (3) | O171—C17—C18 | 120.2 (2) |
C4—C3—C2 | 119.1 (3) | C16—C17—C18 | 118.9 (2) |
C8—C3—C2 | 122.3 (3) | C19—C18—C23 | 118.8 (2) |
C3—C4—C5 | 121.2 (3) | C19—C18—C17 | 123.1 (2) |
C3—C4—H4 | 119.4 | C23—C18—C17 | 118.0 (2) |
C5—C4—H4 | 119.4 | C18—C19—C20 | 120.4 (3) |
C6—C5—C4 | 119.5 (3) | C18—C19—H19 | 119.8 |
C6—C5—H5 | 120.2 | C20—C19—H19 | 119.8 |
C4—C5—H5 | 120.2 | C21—C20—C19 | 120.0 (3) |
C7—C6—C5 | 119.7 (3) | C21—C20—H20 | 120.0 |
C7—C6—H6 | 120.2 | C19—C20—H20 | 120.0 |
C5—C6—H6 | 120.2 | C22—C21—C20 | 120.1 (3) |
C6—C7—C8 | 120.6 (3) | C22—C21—H21 | 119.9 |
C6—C7—H7 | 119.7 | C20—C21—H21 | 119.9 |
C8—C7—H7 | 119.7 | C21—C22—C23 | 120.3 (3) |
C7—C8—C3 | 120.4 (3) | C21—C22—H22 | 119.9 |
C7—C8—H8 | 119.8 | C23—C22—H22 | 119.9 |
C3—C8—H8 | 119.8 | C22—C23—C18 | 120.4 (3) |
C14—C9—C10 | 119.9 (2) | C22—C23—H23 | 119.8 |
C14—C9—S1 | 118.77 (19) | C18—C23—H23 | 119.8 |
C10—C9—S1 | 121.27 (18) | O101—C102—H10A | 109.5 |
O101—C10—C11 | 124.1 (2) | O101—C102—H10B | 109.5 |
O101—C10—C9 | 116.9 (2) | H10A—C102—H10B | 109.5 |
C11—C10—C9 | 119.0 (2) | O101—C102—H10C | 109.5 |
C12—C11—C10 | 119.8 (2) | H10A—C102—H10C | 109.5 |
C12—C11—H11 | 120.1 | H10B—C102—H10C | 109.5 |
C10—C11—H11 | 120.1 | C10—O101—C102 | 117.8 (2) |
C11—C12—C13 | 122.5 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O171i | 0.84 (3) | 2.23 (3) | 3.018 (3) | 156 (3) |
Symmetry code: (i) x, y, z−1. |
Experimental details
Crystal data | |
Chemical formula | C23H21NO4S |
Mr | 407.47 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 10.3671 (12), 10.3750 (8), 10.7977 (14) |
α, β, γ (°) | 84.88 (1), 68.79 (1), 65.40 (1) |
V (Å3) | 981.9 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.20 |
Crystal size (mm) | 0.50 × 0.33 × 0.13 |
Data collection | |
Diffractometer | Enraf-Nonius CAD-4 |
Absorption correction | ψ scan (PLATON; Spek, 2003; North et al., 1968) |
Tmin, Tmax | 0.924, 0.969 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3694, 3490, 2573 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.597 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.135, 1.05 |
No. of reflections | 3490 |
No. of parameters | 266 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.35, −0.47 |
Computer programs: CAD-4 EXPRESS (Enraf-Nonius, 1994), CAD-4 EXPRESS, HELENA (Spek, 1996), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003) and Mercury (Macrae et al., 2006), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O171i | 0.84 (3) | 2.23 (3) | 3.018 (3) | 156 (3) |
Symmetry code: (i) x, y, z−1. |
Sulfonamide is a pharmacophoric group of over than 30 pharmaceuticals which are in clinical use, with antibacterial, diuretic, oral antidiabetic, HIV protease inhibitory (Supuran et al., 2003) and antimalarial (Petersen, 2004) activities. Many novel sulfonamide derivatives have recently been reported to show carbonic anhydrase inhibitory action, matrix metalloproteinase inhibitory action, endothelin receptor antagonism, antitumoral (Supuran et al., 2003) and antileishmanial (Bhattacharya et al., 2004) activities.
Naturally occurring and synthetic chalcones are known to have a wide range of potential pharmacological activities, such as anti-inflammatory, antibacterial, anticancer, antiviral, antimalarial (Ni et al., 2004), antitrypanosomal, antileishmanial (Lunardi et al., 2003) and nitric oxide inhibitory action (Rojas et al., 2002). A combination of two or more pharmacophoric groups can enhance the discovery probability of new lead compounds, specially if closely related activities are involved. Recently, analogs of sulfonamide chalcone derivatives were synthesized and showed activity against cultured Plasmodium falciparum parasites (Dominguez et al., 2005). In order to investigate of bioactivity of the combined compounds, we have prepared some sulfonamide chalcone derivatives, and in this paper we present the synthesis and X-ray study of (I).
The molecule of (I) shows an angular geometry (Fig. 1) resulting from the structural combination of sulfonamide and chalcone moieties, with the vertices of the molecule occupied by S atom. The chalcone arm is quasi planar, where the dihedral angles between the best planes of the rings C9···C14 and C18···C23 is 10.85 (6)° and the best plane of the central chain C13—C15═ C16—C17 with respect to phenyl rings C9···C14 and C18···C23 are 10.4 (1)° and 11.6 (1)°, respectively. This feature suggests that there is electronic delocalization forming an extended π -electron conjugated system in this moiety. It is in accord with decreased length of the C16—C17 [1.471 (3) Å] single bond and the increased length of the C15═C16 [1.322 (4) Å] double bond. In addition, the methoxy group is also almost coplanar with its attached phenyl ring. It was observed in similar structures of chalcone (Subbiah Pandi et al., 2003 and cited references) when the mehtoxy is in para position with respect to the central chain. In the sulfonamide moiety, the distances and angles around N1 and C2 are within the expected range found in similar structures searched in CSD V5.28 with Mogul (Bruno et al., 2004). The phenyl ring C3···C8 is almost perpendicular to the mean plane of the chalcone arm, where the dihedral angle between these planes is 85.04 (8)°. An intermolecular hydrogen bond [N1—H1···O171i, NH = 0.84 (3) Å, H···O = 2.23 (3) Å, N—H···O = 156 (3)°, symmetry code: (i) x, y, z - 1] promotes a zigzag infinite chain formation running parallel to the crystallographic [001] axis (Fig. 2), keeping the molecules stacked in this direction.