Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270105023759/av1251sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270105023759/av1251Isup2.hkl |
CCDC reference: 285801
The synthesis of compound (I) was performed according to the reported method of Ayhan-Kilcigil et al. (2003). A mixture of 6-bromomethylflavone, (1) (157 mg, 0.5 mmol), 4-amino-N-(5-methyl-3-isoxazoyl)benzensulfonamide, (2) (0.5 mmol) and anhydrous potassium carbonate (69 mg, 0.5 mmol) was stirred at 333 K in dimethylformamide (10 ml) until the starting materials were used up. Water was added (Volume?) and the mixture was extracted with CHCl3. The extract was washed with water and purified by column chromatography and then recrystallized from ethanol. The structure was assigned by NMR and mass spectroscopies and elemental analysis results.
The H atoms at N3 were located in a difference Fourier map and refined with fixed individual displacement parameters [Uiso(H) = 1.2Ueq(N3)]. The methyl H atoms were also located by difference Fourier synthesis and refined as a rigid group, with Uiso(H) = 1.5Ueq(C21). All other H atoms were placed in idealized positions and refined using a riding model, with C—H distances of 0.93 Å (aromatic) and 0.97 Å (methylene).
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).
C26H21N3O5S | F(000) = 1016 |
Mr = 487.53 | Dx = 1.408 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.824 (2) Å | Cell parameters from 20 reflections |
b = 23.183 (4) Å | θ = 9.2–18.1° |
c = 11.305 (3) Å | µ = 0.19 mm−1 |
β = 96.185 (2)° | T = 295 K |
V = 2299.2 (9) Å3 | Prism, colourless |
Z = 4 | 0.48 × 0.36 × 0.21 mm |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.080 |
non–profiled ω scans | θmax = 26.3°, θmin = 2.5° |
Absorption correction: ψ scan (North et al., 1968) | h = −10→10 |
Tmin = 0.923, Tmax = 0.962 | k = 0→28 |
4875 measured reflections | l = 0→14 |
4641 independent reflections | 3 standard reflections every 120 min |
2022 reflections with I > 2σ(I) | intensity decay: 3% |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.055 | w = 1/[σ2(Fo2) + (0.0555P)2 + 0.04sinθ/λ] where P = 0.33333Fo2 + 0.66667Fc2 |
wR(F2) = 0.146 | (Δ/σ)max < 0.001 |
S = 0.97 | Δρmax = 0.27 e Å−3 |
4641 reflections | Δρmin = −0.33 e Å−3 |
322 parameters |
C26H21N3O5S | V = 2299.2 (9) Å3 |
Mr = 487.53 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.824 (2) Å | µ = 0.19 mm−1 |
b = 23.183 (4) Å | T = 295 K |
c = 11.305 (3) Å | 0.48 × 0.36 × 0.21 mm |
β = 96.185 (2)° |
Enraf–Nonius CAD-4 diffractometer | 2022 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.080 |
Tmin = 0.923, Tmax = 0.962 | 3 standard reflections every 120 min |
4875 measured reflections | intensity decay: 3% |
4641 independent reflections |
R[F2 > 2σ(F2)] = 0.055 | 0 restraints |
wR(F2) = 0.146 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.97 | Δρmax = 0.27 e Å−3 |
4641 reflections | Δρmin = −0.33 e Å−3 |
322 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
C2 | 0.8412 (4) | 0.10803 (16) | −0.0605 (3) | 0.0361 (9) | |
C3 | 0.8691 (4) | 0.05829 (17) | −0.1143 (3) | 0.0451 (10) | |
H3 | 0.9221 | 0.0593 | −0.1811 | 0.054* | |
C4 | 0.8199 (4) | 0.00293 (18) | −0.0725 (3) | 0.0426 (10) | |
C5 | 0.6835 (4) | −0.04236 (16) | 0.0883 (3) | 0.0407 (10) | |
H5 | 0.7024 | −0.0788 | 0.0587 | 0.049* | |
C6 | 0.6049 (4) | −0.03795 (17) | 0.1851 (3) | 0.0376 (9) | |
C7 | 0.5753 (4) | 0.01663 (17) | 0.2284 (3) | 0.0466 (11) | |
H7 | 0.5193 | 0.0203 | 0.2931 | 0.056* | |
C8 | 0.6280 (4) | 0.06499 (17) | 0.1764 (3) | 0.0455 (11) | |
H8 | 0.6092 | 0.1013 | 0.2066 | 0.055* | |
C9 | 0.7086 (4) | 0.05971 (16) | 0.0797 (3) | 0.0353 (9) | |
C10 | 0.7365 (4) | 0.00604 (16) | 0.0320 (3) | 0.0369 (9) | |
C11 | 0.8896 (4) | 0.16626 (16) | −0.0930 (3) | 0.0367 (9) | |
C12 | 0.8493 (5) | 0.21454 (18) | −0.0317 (4) | 0.0519 (12) | |
H12 | 0.7908 | 0.2103 | 0.0314 | 0.062* | |
C13 | 0.8948 (5) | 0.26922 (19) | −0.0630 (4) | 0.0584 (13) | |
H13 | 0.8668 | 0.3015 | −0.0215 | 0.07* | |
C14 | 0.9817 (5) | 0.2752 (2) | −0.1558 (4) | 0.0596 (12) | |
H14 | 1.0128 | 0.3117 | −0.177 | 0.071* | |
C15 | 1.0229 (5) | 0.2282 (2) | −0.2173 (4) | 0.0595 (13) | |
H15 | 1.0813 | 0.2328 | −0.2804 | 0.071* | |
C16 | 0.9780 (5) | 0.17356 (18) | −0.1861 (3) | 0.0475 (11) | |
H16 | 1.0073 | 0.1416 | −0.2278 | 0.057* | |
C17 | 0.5470 (4) | −0.09079 (17) | 0.2439 (3) | 0.0439 (10) | |
H17A | 0.4403 | −0.0965 | 0.216 | 0.053* | |
H17B | 0.6029 | −0.1244 | 0.2215 | 0.053* | |
C18 | 0.7170 (4) | −0.08318 (15) | 0.4293 (3) | 0.0346 (9) | |
C19 | 0.7727 (5) | −0.06153 (17) | 0.5414 (3) | 0.0451 (11) | |
H19 | 0.7167 | −0.0459 | 0.5988 | 0.054* | |
C20 | 0.9233 (5) | −0.06817 (17) | 0.5478 (4) | 0.0469 (11) | |
C21 | 1.0550 (5) | −0.0570 (2) | 0.6385 (4) | 0.0690 (14) | |
H21A | 1.1406 | −0.0443 | 0.5998 | 0.104* | |
H21B | 1.0812 | −0.0919 | 0.6819 | 0.104* | |
H21C | 1.0281 | −0.0277 | 0.6926 | 0.104* | |
C22 | 0.5044 (4) | −0.19781 (16) | 0.4128 (3) | 0.0350 (9) | |
C23 | 0.6299 (4) | −0.22270 (17) | 0.4791 (3) | 0.0446 (10) | |
H23 | 0.6744 | −0.2047 | 0.5477 | 0.053* | |
C24 | 0.6880 (5) | −0.27429 (18) | 0.4425 (4) | 0.0471 (11) | |
H24 | 0.7702 | −0.2913 | 0.488 | 0.056* | |
C25 | 0.6251 (5) | −0.30105 (17) | 0.3390 (4) | 0.0425 (10) | |
C26 | 0.4958 (5) | −0.27638 (17) | 0.2757 (3) | 0.0461 (11) | |
H26 | 0.4489 | −0.2949 | 0.2085 | 0.055* | |
C27 | 0.4378 (4) | −0.22524 (17) | 0.3118 (3) | 0.0424 (10) | |
H27 | 0.3532 | −0.2089 | 0.2681 | 0.051* | |
N1 | 0.5644 (3) | −0.08534 (12) | 0.3748 (2) | 0.0367 (8) | |
N2 | 0.8244 (4) | −0.10124 (16) | 0.3699 (3) | 0.0574 (10) | |
N3 | 0.6905 (5) | −0.34931 (17) | 0.2971 (4) | 0.0590 (12) | |
H31 | 0.753 (5) | −0.3677 (19) | 0.343 (4) | 0.072* | |
H32 | 0.648 (5) | −0.3635 (19) | 0.232 (4) | 0.072* | |
O1 | 0.7609 (3) | 0.10986 (11) | 0.0345 (2) | 0.0438 (7) | |
O2 | 0.8475 (3) | −0.04320 (12) | −0.1212 (3) | 0.0640 (9) | |
O3 | 0.9597 (3) | −0.09197 (13) | 0.4456 (3) | 0.0630 (9) | |
O4 | 0.2989 (3) | −0.11764 (11) | 0.3856 (2) | 0.0503 (7) | |
O5 | 0.4815 (3) | −0.11605 (11) | 0.5678 (2) | 0.0482 (7) | |
S1 | 0.44815 (11) | −0.12814 (4) | 0.44347 (9) | 0.0391 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C2 | 0.039 (2) | 0.040 (2) | 0.030 (2) | 0.0017 (18) | 0.0054 (18) | −0.0009 (19) |
C3 | 0.061 (3) | 0.046 (3) | 0.031 (2) | −0.003 (2) | 0.015 (2) | −0.002 (2) |
C4 | 0.050 (3) | 0.042 (3) | 0.035 (2) | −0.005 (2) | 0.003 (2) | −0.007 (2) |
C5 | 0.051 (2) | 0.034 (2) | 0.037 (2) | 0.000 (2) | 0.004 (2) | −0.0019 (19) |
C6 | 0.037 (2) | 0.043 (3) | 0.033 (2) | −0.0018 (19) | 0.0038 (19) | 0.0013 (19) |
C7 | 0.052 (3) | 0.051 (3) | 0.041 (2) | 0.007 (2) | 0.022 (2) | 0.002 (2) |
C8 | 0.056 (3) | 0.034 (2) | 0.049 (3) | 0.010 (2) | 0.015 (2) | 0.001 (2) |
C9 | 0.035 (2) | 0.035 (2) | 0.036 (2) | 0.0026 (19) | 0.0064 (19) | 0.0043 (19) |
C10 | 0.037 (2) | 0.039 (3) | 0.034 (2) | 0.0025 (19) | −0.0011 (19) | −0.003 (2) |
C11 | 0.039 (2) | 0.037 (2) | 0.035 (2) | 0.0008 (19) | 0.0048 (18) | −0.005 (2) |
C12 | 0.064 (3) | 0.044 (3) | 0.051 (3) | −0.002 (2) | 0.022 (2) | −0.001 (2) |
C13 | 0.068 (3) | 0.039 (3) | 0.069 (3) | 0.001 (2) | 0.014 (3) | −0.006 (2) |
C14 | 0.072 (3) | 0.049 (3) | 0.059 (3) | −0.009 (3) | 0.009 (3) | 0.004 (3) |
C15 | 0.068 (3) | 0.062 (3) | 0.051 (3) | −0.013 (3) | 0.019 (2) | 0.003 (3) |
C16 | 0.057 (3) | 0.044 (3) | 0.043 (3) | −0.002 (2) | 0.014 (2) | −0.006 (2) |
C17 | 0.050 (3) | 0.048 (3) | 0.034 (2) | −0.007 (2) | 0.004 (2) | −0.002 (2) |
C18 | 0.037 (2) | 0.027 (2) | 0.041 (2) | −0.0003 (18) | 0.012 (2) | −0.0036 (19) |
C19 | 0.046 (3) | 0.047 (3) | 0.043 (3) | −0.006 (2) | 0.010 (2) | −0.008 (2) |
C20 | 0.058 (3) | 0.042 (3) | 0.040 (3) | −0.007 (2) | 0.003 (2) | 0.002 (2) |
C21 | 0.064 (3) | 0.073 (3) | 0.066 (3) | −0.021 (3) | −0.013 (3) | 0.010 (3) |
C22 | 0.037 (2) | 0.033 (2) | 0.034 (2) | −0.0015 (18) | 0.0023 (19) | 0.0017 (18) |
C23 | 0.053 (3) | 0.043 (3) | 0.037 (2) | −0.003 (2) | 0.002 (2) | −0.003 (2) |
C24 | 0.048 (3) | 0.047 (3) | 0.045 (3) | 0.005 (2) | −0.003 (2) | 0.007 (2) |
C25 | 0.051 (3) | 0.032 (2) | 0.046 (3) | −0.003 (2) | 0.009 (2) | 0.004 (2) |
C26 | 0.057 (3) | 0.037 (3) | 0.043 (3) | −0.005 (2) | −0.002 (2) | −0.006 (2) |
C27 | 0.048 (3) | 0.038 (2) | 0.039 (2) | −0.005 (2) | −0.004 (2) | 0.003 (2) |
N1 | 0.038 (2) | 0.0416 (19) | 0.0308 (18) | −0.0027 (15) | 0.0058 (15) | 0.0010 (16) |
N2 | 0.042 (2) | 0.075 (3) | 0.054 (2) | 0.0060 (19) | 0.0008 (19) | −0.016 (2) |
N3 | 0.072 (3) | 0.045 (3) | 0.059 (3) | 0.010 (2) | 0.001 (2) | −0.008 (2) |
O1 | 0.0543 (17) | 0.0363 (17) | 0.0438 (16) | 0.0018 (13) | 0.0184 (14) | 0.0019 (13) |
O2 | 0.095 (2) | 0.0427 (19) | 0.060 (2) | −0.0093 (17) | 0.0343 (18) | −0.0151 (16) |
O3 | 0.0405 (18) | 0.076 (2) | 0.072 (2) | 0.0109 (17) | 0.0038 (16) | −0.0103 (19) |
O4 | 0.0307 (15) | 0.0575 (19) | 0.0623 (19) | 0.0052 (14) | 0.0039 (14) | 0.0009 (15) |
O5 | 0.0614 (18) | 0.0533 (19) | 0.0325 (16) | −0.0027 (14) | 0.0173 (13) | −0.0048 (13) |
S1 | 0.0403 (6) | 0.0371 (6) | 0.0416 (6) | −0.0015 (5) | 0.0117 (5) | −0.0013 (5) |
C2—C3 | 1.339 (5) | C17—H17A | 0.97 |
C2—O1 | 1.349 (4) | C17—H17B | 0.97 |
C2—C11 | 1.474 (5) | C18—N2 | 1.289 (4) |
C3—C4 | 1.450 (5) | C18—C19 | 1.402 (5) |
C3—H3 | 0.93 | C18—N1 | 1.420 (4) |
C4—O2 | 1.239 (4) | C19—C20 | 1.332 (5) |
C4—C10 | 1.460 (5) | C19—H19 | 0.93 |
C5—C6 | 1.361 (5) | C20—O3 | 1.351 (4) |
C5—C10 | 1.395 (5) | C20—C21 | 1.487 (5) |
C5—H5 | 0.93 | C21—H21A | 0.96 |
C6—C7 | 1.391 (5) | C21—H21B | 0.96 |
C6—C17 | 1.509 (5) | C21—H21C | 0.96 |
C7—C8 | 1.370 (5) | C22—C27 | 1.381 (5) |
C7—H7 | 0.93 | C22—C23 | 1.394 (5) |
C8—C9 | 1.372 (5) | C22—S1 | 1.736 (4) |
C8—H8 | 0.93 | C23—C24 | 1.382 (5) |
C9—O1 | 1.370 (4) | C23—H23 | 0.93 |
C9—C10 | 1.389 (5) | C24—C25 | 1.387 (5) |
C11—C12 | 1.383 (5) | C24—H24 | 0.93 |
C11—C16 | 1.386 (5) | C25—N3 | 1.367 (5) |
C12—C13 | 1.387 (5) | C25—C26 | 1.402 (5) |
C12—H12 | 0.93 | C26—C27 | 1.371 (5) |
C13—C14 | 1.371 (5) | C26—H26 | 0.93 |
C13—H13 | 0.93 | C27—H27 | 0.93 |
C14—C15 | 1.363 (6) | N1—S1 | 1.676 (3) |
C14—H14 | 0.93 | N2—O3 | 1.408 (4) |
C15—C16 | 1.384 (5) | N3—H31 | 0.83 (4) |
C15—H15 | 0.93 | N3—H32 | 0.86 (4) |
C16—H16 | 0.93 | O4—S1 | 1.427 (3) |
C17—N1 | 1.476 (4) | O5—S1 | 1.433 (2) |
C3—C2—O1 | 121.8 (4) | H17A—C17—H17B | 108 |
C3—C2—C11 | 127.1 (3) | N2—C18—C19 | 112.4 (4) |
O1—C2—C11 | 111.2 (3) | N2—C18—N1 | 118.6 (3) |
C2—C3—C4 | 122.5 (4) | C19—C18—N1 | 129.0 (3) |
C2—C3—H3 | 118.7 | C20—C19—C18 | 105.0 (4) |
C4—C3—H3 | 118.7 | C20—C19—H19 | 127.5 |
O2—C4—C3 | 122.6 (4) | C18—C19—H19 | 127.5 |
O2—C4—C10 | 122.9 (4) | C19—C20—O3 | 109.2 (4) |
C3—C4—C10 | 114.5 (4) | C19—C20—C21 | 135.9 (4) |
C6—C5—C10 | 122.1 (4) | O3—C20—C21 | 114.9 (4) |
C6—C5—H5 | 119 | C20—C21—H21A | 109.5 |
C10—C5—H5 | 119 | C20—C21—H21B | 109.5 |
C5—C6—C7 | 118.8 (4) | H21A—C21—H21B | 109.5 |
C5—C6—C17 | 121.3 (4) | C20—C21—H21C | 109.5 |
C7—C6—C17 | 119.9 (3) | H21A—C21—H21C | 109.5 |
C8—C7—C6 | 120.5 (4) | H21B—C21—H21C | 109.5 |
C8—C7—H7 | 119.7 | C27—C22—C23 | 119.8 (4) |
C6—C7—H7 | 119.7 | C27—C22—S1 | 119.2 (3) |
C7—C8—C9 | 119.9 (4) | C23—C22—S1 | 120.4 (3) |
C7—C8—H8 | 120.1 | C24—C23—C22 | 119.7 (4) |
C9—C8—H8 | 120.1 | C24—C23—H23 | 120.1 |
O1—C9—C8 | 116.5 (3) | C22—C23—H23 | 120.1 |
O1—C9—C10 | 122.3 (3) | C23—C24—C25 | 120.8 (4) |
C8—C9—C10 | 121.2 (4) | C23—C24—H24 | 119.6 |
C9—C10—C5 | 117.5 (3) | C25—C24—H24 | 119.6 |
C9—C10—C4 | 119.0 (3) | N3—C25—C24 | 120.9 (4) |
C5—C10—C4 | 123.5 (4) | N3—C25—C26 | 120.5 (4) |
C12—C11—C16 | 118.5 (4) | C24—C25—C26 | 118.6 (4) |
C12—C11—C2 | 121.3 (3) | C27—C26—C25 | 120.7 (4) |
C16—C11—C2 | 120.2 (3) | C27—C26—H26 | 119.7 |
C11—C12—C13 | 121.0 (4) | C25—C26—H26 | 119.7 |
C11—C12—H12 | 119.5 | C26—C27—C22 | 120.3 (4) |
C13—C12—H12 | 119.5 | C26—C27—H27 | 119.8 |
C14—C13—C12 | 119.2 (4) | C22—C27—H27 | 119.8 |
C14—C13—H13 | 120.4 | C18—N1—C17 | 115.4 (3) |
C12—C13—H13 | 120.4 | C18—N1—S1 | 114.8 (2) |
C15—C14—C13 | 120.8 (4) | C17—N1—S1 | 114.2 (2) |
C15—C14—H14 | 119.6 | C18—N2—O3 | 104.9 (3) |
C13—C14—H14 | 119.6 | C25—N3—H31 | 119 (3) |
C14—C15—C16 | 120.1 (4) | C25—N3—H32 | 117 (3) |
C14—C15—H15 | 120 | H31—N3—H32 | 123 (5) |
C16—C15—H15 | 120 | C2—O1—C9 | 119.8 (3) |
C15—C16—C11 | 120.4 (4) | C20—O3—N2 | 108.5 (3) |
C15—C16—H16 | 119.8 | O4—S1—O5 | 119.89 (16) |
C11—C16—H16 | 119.8 | O4—S1—N1 | 105.50 (16) |
N1—C17—C6 | 111.7 (3) | O5—S1—N1 | 105.49 (15) |
N1—C17—H17A | 109.3 | O4—S1—C22 | 109.70 (17) |
C6—C17—H17A | 109.3 | O5—S1—C22 | 110.20 (17) |
N1—C17—H17B | 109.3 | N1—S1—C22 | 104.81 (16) |
C6—C17—H17B | 109.3 | ||
O1—C2—C3—C4 | −2.1 (6) | C18—C19—C20—C21 | −178.0 (5) |
C11—C2—C3—C4 | 178.1 (4) | C27—C22—C23—C24 | 0.8 (5) |
C2—C3—C4—O2 | −178.9 (4) | S1—C22—C23—C24 | −170.0 (3) |
C2—C3—C4—C10 | 0.6 (6) | C22—C23—C24—C25 | 1.5 (6) |
C10—C5—C6—C7 | 0.7 (6) | C23—C24—C25—N3 | 174.2 (4) |
C10—C5—C6—C17 | 179.4 (3) | C23—C24—C25—C26 | −3.6 (6) |
C5—C6—C7—C8 | −1.7 (6) | N3—C25—C26—C27 | −174.3 (4) |
C17—C6—C7—C8 | 179.5 (4) | C24—C25—C26—C27 | 3.5 (6) |
C6—C7—C8—C9 | 1.0 (6) | C25—C26—C27—C22 | −1.3 (6) |
C7—C8—C9—O1 | −178.4 (3) | C23—C22—C27—C26 | −0.9 (5) |
C7—C8—C9—C10 | 0.8 (6) | S1—C22—C27—C26 | 170.0 (3) |
O1—C9—C10—C5 | 177.3 (3) | N2—C18—N1—C17 | −18.5 (5) |
C8—C9—C10—C5 | −1.9 (5) | C19—C18—N1—C17 | 158.9 (4) |
O1—C9—C10—C4 | −2.2 (5) | N2—C18—N1—S1 | 117.6 (3) |
C8—C9—C10—C4 | 178.7 (3) | C19—C18—N1—S1 | −65.1 (5) |
C6—C5—C10—C9 | 1.1 (5) | C6—C17—N1—C18 | −65.7 (4) |
C6—C5—C10—C4 | −179.4 (4) | C6—C17—N1—S1 | 158.0 (2) |
O2—C4—C10—C9 | −179.0 (4) | C19—C18—N2—O3 | 0.6 (4) |
C3—C4—C10—C9 | 1.5 (5) | N1—C18—N2—O3 | 178.3 (3) |
O2—C4—C10—C5 | 1.5 (6) | C3—C2—O1—C9 | 1.5 (5) |
C3—C4—C10—C5 | −178.0 (3) | C11—C2—O1—C9 | −178.7 (3) |
C3—C2—C11—C12 | 178.1 (4) | C8—C9—O1—C2 | 179.9 (3) |
O1—C2—C11—C12 | −1.7 (5) | C10—C9—O1—C2 | 0.7 (5) |
C3—C2—C11—C16 | −2.3 (6) | C19—C20—O3—N2 | −0.3 (4) |
O1—C2—C11—C16 | 177.8 (3) | C21—C20—O3—N2 | 178.6 (3) |
C16—C11—C12—C13 | 0.6 (6) | C18—N2—O3—C20 | −0.2 (4) |
C2—C11—C12—C13 | −179.8 (4) | C18—N1—S1—O4 | 171.8 (2) |
C11—C12—C13—C14 | −0.3 (6) | C17—N1—S1—O4 | −51.6 (3) |
C12—C13—C14—C15 | 0.2 (7) | C18—N1—S1—O5 | 44.0 (3) |
C13—C14—C15—C16 | −0.4 (7) | C17—N1—S1—O5 | −179.5 (3) |
C14—C15—C16—C11 | 0.7 (6) | C18—N1—S1—C22 | −72.4 (3) |
C12—C11—C16—C15 | −0.8 (6) | C17—N1—S1—C22 | 64.2 (3) |
C2—C11—C16—C15 | 179.7 (4) | C27—C22—S1—O4 | 23.4 (3) |
C5—C6—C17—N1 | 140.6 (4) | C23—C22—S1—O4 | −165.8 (3) |
C7—C6—C17—N1 | −40.7 (5) | C27—C22—S1—O5 | 157.4 (3) |
N2—C18—C19—C20 | −0.7 (5) | C23—C22—S1—O5 | −31.7 (3) |
N1—C18—C19—C20 | −178.2 (4) | C27—C22—S1—N1 | −89.5 (3) |
C18—C19—C20—O3 | 0.6 (4) | C23—C22—S1—N1 | 81.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···O1 | 0.93 | 2.34 | 2.680 (5) | 101 |
C17—H17A···O4 | 0.97 | 2.45 | 2.916 (4) | 109 |
C27—H27···O4 | 0.93 | 2.57 | 2.940 (5) | 104 |
N3—H32···O5i | 0.86 (5) | 2.29 (4) | 3.120 (5) | 164 (4) |
N3—H31···O2ii | 0.83 (4) | 2.25 (4) | 2.951 (5) | 142 (4) |
C16—H16···N2iii | 0.93 | 2.49 | 3.309 (5) | 148 |
Symmetry codes: (i) x, −y−1/2, z−1/2; (ii) x, −y−1/2, z+1/2; (iii) −x+2, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C26H21N3O5S |
Mr | 487.53 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 295 |
a, b, c (Å) | 8.824 (2), 23.183 (4), 11.305 (3) |
β (°) | 96.185 (2) |
V (Å3) | 2299.2 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.19 |
Crystal size (mm) | 0.48 × 0.36 × 0.21 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.923, 0.962 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4875, 4641, 2022 |
Rint | 0.080 |
(sin θ/λ)max (Å−1) | 0.623 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.055, 0.146, 0.97 |
No. of reflections | 4641 |
No. of parameters | 322 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.27, −0.33 |
Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), CAD-4 EXPRESS, XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003), WinGX (Farrugia, 1999).
C2—C3 | 1.339 (5) | C18—N2 | 1.289 (4) |
C2—O1 | 1.349 (4) | C18—N1 | 1.420 (4) |
C2—C11 | 1.474 (5) | C19—C20 | 1.332 (5) |
C4—O2 | 1.239 (4) | C25—N3 | 1.367 (5) |
C6—C17 | 1.509 (5) | N1—S1 | 1.676 (3) |
C9—O1 | 1.370 (4) | O4—S1 | 1.427 (3) |
C17—N1 | 1.476 (4) | O5—S1 | 1.433 (2) |
C2—C3—C4 | 122.5 (4) | O4—S1—O5 | 119.89 (16) |
N1—C17—C6 | 111.7 (3) | O5—S1—N1 | 105.49 (15) |
C18—N1—C17 | 115.4 (3) | O4—S1—C22 | 109.70 (17) |
C18—N1—S1 | 114.8 (2) | ||
O1—C2—C11—C16 | 177.8 (3) | C6—C17—N1—S1 | 158.0 (2) |
C5—C6—C17—N1 | 140.6 (4) | C18—N1—S1—C22 | −72.4 (3) |
N2—C18—N1—S1 | 117.6 (3) | C27—C22—S1—N1 | −89.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···O1 | 0.93 | 2.34 | 2.680 (5) | 101 |
C17—H17A···O4 | 0.97 | 2.45 | 2.916 (4) | 109 |
C27—H27···O4 | 0.93 | 2.57 | 2.940 (5) | 104 |
N3—H32···O5i | 0.86 (5) | 2.29 (4) | 3.120 (5) | 164 (4) |
N3—H31···O2ii | 0.83 (4) | 2.25 (4) | 2.951 (5) | 142 (4) |
C16—H16···N2iii | 0.93 | 2.49 | 3.309 (5) | 148 |
Symmetry codes: (i) x, −y−1/2, z−1/2; (ii) x, −y−1/2, z+1/2; (iii) −x+2, −y, −z. |
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Flavonoids form a class of benzo-γ-pyrone derivatives and include flavones, flavanes, flavonols, anthocyanidines and catechins. They possess a wide spectrum of biological activities, such as anticancer (Zharko et al., 1986), antibacterial (Mori et al., 1987), antifungal (Perry & Foster, 1994), antiviral (Wleklik et al., 1988), spasmolytic (Ertan et al., 1989), hypoglycaemic (Bozdağ-Dündar et al., 2001), antihistaminic (Amella et al., 1985) and antioxidant (Czompa et al., 2000). Furthermore, it is well documented that sulfonamide derivatives have been used in particular against urinary tract infections caused by Escherichia coli (Mutschler et al., 2001). In view of reports indicating that derivatives of flavone exhibit antimicrobial activity (Ayhan-Kilcigil et al., 1999; Ayhan-Kilcigil & Altanlar, 2000; Tunçbilek et al., 1999), we have described the synthesis and antimicrobial evaluation of new sulfonamide derivatives having a flavone ring system (Reference?).
In order to gain more information about the relationship between structural features and biological properties, in the last decade we have also carried out crystallographic studies on several molecules of this family (Kendi et al., 1994, 1995a,b, 1996, 2000; Özbey et al., 1997, 1999; Ayhan-Kilcigil et al., 1998; Tunçbilek et al., 1999). As part of this research, we present here the crystal structure of the title novel sulfonamide derivative, (I). The compound was also tested for antimicrobial activity by the Agar diffusion method against E. coli and the result was compared with that of the corresponding sulphonamide derivative, (2). According to the result of this test, compound (I) shows better activity than the corresponding sulfonamide against E. coli (Ayhan-Kilcigil et al., 2003).
The molecule of the title compound consists of sulfamethoxazole and flavone moieties. The flavone moiety of the molecule is almost planar; the dihedral angle between the best planes of the benzopyran and phenyl rings, which are both planar as expected, is 2.8 (2)°. This value is comparable with those of 5,7-dihydroxy-8-methoxyflavone (2.8°; Jiang et al., 2002), 5,7-dihydroxy-4'-methoxyflavone (3.1°; Cantrell, 1986) and 1,4-dihydro-2,6-dimethyl-4-[4-(4H-4-oxo-1-benzopyran-2-yl)phenyl]-3,5-pyridine dicarboxylate (3.3°; Kendi et al., 1994). However, it is significantly smaller than those in flavone-3'-sulfonamide (8.3°; Kendi et al., 2000), 2-(2-ethoxycarbonyl-1,4-benzodioxan-7-yl)-4H-1-benzopyran-4-one (13.9°; Özbey et al., 1997), 2–6-dimethyl-4-(2-phenyl-4-oxo-4H-1- benzopyran-6-yl-)-1,4-dihydropyridine-3,5-dicarboxylate (10.7°; Özbey et al., 1999) and 2'-methyl-3'-nitroflavone (139.8°; Kendi et al., 1996), due to the steric hindrance caused by the groups attached to the phenyl ring.
The coplanarity of the phenyl ring and the benzopyran plane has been attributed to a short intramolecular hydrogen contact between an H atom of the phenyl and atom O1 of the pyrone (Table 2). Similar intramolecular hydrogen-bond interactions are reported for 2'-methoxyflavone (Wallet et al., 1990), 6-(3-hydroxy-3-methylbut-1-yl)flavone and 6-(3-methylbut-3-en-1-ynyl)flavone (Artali et al., 2003) and 2-(2-Ethoxycarbonyl-1,4-benzodioxan-7-yl)-4H-1-benzopyran-4-one (Özbey et al., 1997).
The atoms around the S atom in the sulfonamide of (I) are arranged in a slightly distorted tetrahedral configuration. The largest deviation is in the angle O4—S1—O5 [119.9 (2)°], but it conforms to the non-tetrahedral nature commonly observed in sulphonamides (Chatterjee et al., 1982; Haridas et al., 1984; Ghosh et al., 1991; Kendi et al., 2000; Takasuka & Nakai, 2001). In this configuration, the sulfonyl atom O4 takes part in short intramolecular hydrogen contacts with atoms C17 and C27, forming a five-membered ring structure.
The isoxazole and aminophenyl rings at N1 and S1, respectively, are essentially planar and form an angle of 40.7 (2)°. In related molecules, the torsion angles ε1 (C—C—S—N) and ε2 (C—S—N—C) defining the conformation of the sulfonamide group are reported to lie in the ranges 70–120 and 60–90°, respectively (Kálmán et al., 1981). In the present structure, the C23—C22—S1—N1 and C22—S1—N1—C17 torsion angles of 81.4 (3) and 64.2 (3)°, respectively, lie within these ranges. The flavone moiety is rotated around the N1—C17 and C17—C6 bonds, giving torsion angles S1—N1—C17—C6 = 158.0 (2)° and N1—C17—C6—C5 = 140.6 (4)°. As far as the interatomic distances and bond angles of the title compound are concerned, those of both the sulfamethoxazole and the flavone moieties agree well with their equivalents in similar structures.
The packing of the molecules and the hydrogen bonding in the structure are shown in Fig. 2. A l l O and N atoms, except N1 and O3, participate in hydrogen bonds and short intramolecular contacts (Table 2). Atom N3 of the arylamino moiety is involved in two intermolecular hydrogen bonds with the sulfonyl atom O5 and flavone atom O2. The isoxazole atom N2 takes part in a relatively weak hydrogen bond with atom C16 of the flavone. The packing is also characterized by an overlap of the benzopyran moieties, related by a centre at (1/2,0,0), at an interplanar distance of less than 3.7 Å.