Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806017156/lh2068sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806017156/lh2068IIsup2.hkl |
CCDC reference: 610841
Data collection: SMART APEX (Bruker, 2003); cell refinement: SAINT-Plus-NT (Bruker, 2001); data reduction: SAINT-Plus-NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-NT (Sheldrick, 2001); software used to prepare material for publication: SHELXL97.
C15H13N2O+·C7H7O3S− | Z = 2 |
Mr = 408.47 | F(000) = 428 |
Triclinic, P1 | Dx = 1.387 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.9959 (15) Å | Cell parameters from 217 reflections |
b = 7.4103 (16) Å | θ = 4–26° |
c = 21.343 (5) Å | µ = 0.20 mm−1 |
α = 84.138 (3)° | T = 213 K |
β = 85.684 (3)° | Prism, yellow |
γ = 62.749 (2)° | 0.45 × 0.35 × 0.20 mm |
V = 978.0 (4) Å3 |
Bruker SMART CCD diffractometer | 3792 independent reflections |
Radiation source: fine-focus sealed tube | 2891 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
φ and ω scans | θmax = 26.0°, θmin = 2.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −8→8 |
Tmin = 0.925, Tmax = 0.962 | k = −9→8 |
6597 measured reflections | l = −26→26 |
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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.170 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.1088P)2 + 0.3P] where P = (Fo2 + 2Fc2)/3 |
3792 reflections | (Δ/σ)max < 0.001 |
268 parameters | Δρmax = 0.37 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
Experimental. The key features in the NMR spectra were the following: 1H (300 MHz, DMSO-d6) δ 10.94 (s, OH), 8.96 (d, 2H), 8.60 (s, 1H), 8.33 (d, 2H), 8.07 (d, 2H), 7.47 (d, 2H), 7.11 (d, 2H), 7.02 (d, 2H), 4.30 (s, 3H), 2.28 (s, 3H); 13C (75 MHz, DMSO-d6) δ 162.91, 151.37, 149.65, 145.66, 145.49, 137.65, 133.82, 128.06, 125.47, 123.62, 122.23, 116.92, 116.58, 100.10, 47.05, 20.74. |
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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. All C-bound H atoms were placed in geometrically calculated positions and refined using a riding model with C—H distances of 0.94 Å for aromatic and ethylene H atoms, 0.97 Å for CH3 groups. H-atom of HO group was refined isotropically. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.8703 (4) | 0.4138 (4) | 0.27887 (9) | 0.0522 (6) | |
N1 | 0.8223 (4) | 0.0771 (3) | 0.77669 (10) | 0.0372 (5) | |
N2 | 1.3566 (4) | 0.1633 (4) | 0.56885 (11) | 0.0464 (6) | |
C1 | 1.1850 (4) | 0.1817 (4) | 0.57527 (12) | 0.0347 (6) | |
C2 | 0.9982 (4) | 0.1017 (4) | 0.76182 (13) | 0.0408 (6) | |
H2A | 1.0891 | 0.0902 | 0.7939 | 0.049* | |
C3 | 1.0476 (4) | 0.1432 (4) | 0.70098 (12) | 0.0396 (6) | |
H3A | 1.1724 | 0.1596 | 0.6917 | 0.048* | |
C4 | 0.9175 (4) | 0.1617 (4) | 0.65237 (12) | 0.0312 (5) | |
C5 | 0.7326 (4) | 0.1374 (4) | 0.67007 (12) | 0.0375 (6) | |
H5A | 0.6375 | 0.1501 | 0.6391 | 0.045* | |
C6 | 0.6901 (5) | 0.0958 (4) | 0.73119 (12) | 0.0405 (6) | |
H6A | 0.5658 | 0.0796 | 0.7421 | 0.049* | |
C7 | 0.9714 (4) | 0.2001 (4) | 0.58658 (12) | 0.0315 (5) | |
C8 | 0.8357 (4) | 0.2438 (4) | 0.53893 (12) | 0.0309 (5) | |
H8A | 0.7033 | 0.2462 | 0.5521 | 0.037* | |
C9 | 0.8549 (4) | 0.2872 (4) | 0.47211 (11) | 0.0308 (5) | |
C10 | 1.0327 (4) | 0.2961 (4) | 0.43961 (12) | 0.0361 (6) | |
H10A | 1.1537 | 0.2718 | 0.4621 | 0.043* | |
C11 | 1.0331 (4) | 0.3393 (4) | 0.37594 (12) | 0.0386 (6) | |
H11A | 1.1533 | 0.3463 | 0.3553 | 0.046* | |
C12 | 0.8578 (4) | 0.3731 (4) | 0.34120 (12) | 0.0367 (6) | |
C13 | 0.6821 (4) | 0.3599 (4) | 0.37207 (12) | 0.0367 (6) | |
H13A | 0.5640 | 0.3791 | 0.3490 | 0.044* | |
C14 | 0.6812 (4) | 0.3189 (4) | 0.43598 (12) | 0.0333 (6) | |
H14A | 0.5606 | 0.3119 | 0.4563 | 0.040* | |
C15 | 0.7742 (5) | 0.0285 (5) | 0.84279 (12) | 0.0484 (7) | |
H15A | 0.9063 | −0.0684 | 0.8628 | 0.073* | |
H15B | 0.6749 | −0.0301 | 0.8442 | 0.073* | |
H15C | 0.7096 | 0.1519 | 0.8649 | 0.073* | |
S1 | 0.53836 (11) | 0.33230 (11) | 0.17705 (3) | 0.0413 (2) | |
O2 | 0.5449 (4) | 0.4846 (4) | 0.21335 (12) | 0.0732 (8) | |
O3 | 0.5030 (5) | 0.1829 (5) | 0.21529 (15) | 0.0985 (11) | |
O4 | 0.7242 (4) | 0.2523 (4) | 0.13533 (11) | 0.0730 (8) | |
C16 | 0.3131 (4) | 0.4693 (4) | 0.12920 (12) | 0.0347 (6) | |
C17 | 0.3379 (5) | 0.5531 (4) | 0.07046 (12) | 0.0405 (6) | |
H17A | 0.4755 | 0.5317 | 0.0550 | 0.049* | |
C18 | 0.1607 (5) | 0.6684 (4) | 0.03431 (13) | 0.0441 (7) | |
H18A | 0.1790 | 0.7247 | −0.0058 | 0.053* | |
C19 | −0.0423 (5) | 0.7025 (4) | 0.05591 (14) | 0.0430 (7) | |
C20 | −0.0643 (5) | 0.6151 (5) | 0.11483 (14) | 0.0468 (7) | |
H20A | −0.2017 | 0.6350 | 0.1300 | 0.056* | |
C21 | 0.1119 (5) | 0.4989 (4) | 0.15177 (13) | 0.0420 (6) | |
H21A | 0.0944 | 0.4409 | 0.1917 | 0.050* | |
C22 | −0.2365 (6) | 0.8305 (6) | 0.01742 (18) | 0.0649 (9) | |
H22A | −0.1947 | 0.8243 | −0.0270 | 0.097* | |
H22B | −0.2983 | 0.9705 | 0.0284 | 0.097* | |
H22C | −0.3420 | 0.7796 | 0.0260 | 0.097* | |
H1A | 0.751 (8) | 0.440 (7) | 0.262 (2) | 0.108 (17)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0534 (13) | 0.0831 (16) | 0.0317 (10) | −0.0420 (13) | −0.0045 (9) | 0.0031 (10) |
N1 | 0.0421 (13) | 0.0326 (12) | 0.0323 (11) | −0.0125 (10) | −0.0071 (10) | −0.0005 (9) |
N2 | 0.0338 (13) | 0.0605 (16) | 0.0471 (13) | −0.0229 (12) | −0.0047 (10) | −0.0035 (11) |
C1 | 0.0332 (14) | 0.0385 (14) | 0.0335 (13) | −0.0168 (12) | −0.0066 (10) | −0.0008 (11) |
C2 | 0.0374 (15) | 0.0425 (16) | 0.0397 (14) | −0.0144 (13) | −0.0135 (12) | −0.0015 (12) |
C3 | 0.0343 (14) | 0.0454 (16) | 0.0410 (14) | −0.0191 (12) | −0.0100 (11) | 0.0006 (12) |
C4 | 0.0271 (12) | 0.0263 (12) | 0.0368 (13) | −0.0084 (10) | −0.0062 (10) | −0.0028 (10) |
C5 | 0.0352 (14) | 0.0464 (16) | 0.0343 (13) | −0.0209 (12) | −0.0089 (11) | 0.0005 (11) |
C6 | 0.0380 (15) | 0.0481 (16) | 0.0380 (14) | −0.0220 (13) | −0.0066 (11) | 0.0019 (12) |
C7 | 0.0290 (13) | 0.0289 (12) | 0.0368 (13) | −0.0128 (10) | −0.0047 (10) | −0.0027 (10) |
C8 | 0.0254 (12) | 0.0320 (13) | 0.0365 (13) | −0.0140 (10) | −0.0025 (10) | −0.0015 (10) |
C9 | 0.0292 (13) | 0.0281 (12) | 0.0353 (13) | −0.0127 (10) | −0.0050 (10) | −0.0016 (10) |
C10 | 0.0298 (13) | 0.0439 (15) | 0.0397 (14) | −0.0206 (12) | −0.0052 (11) | −0.0029 (11) |
C11 | 0.0359 (14) | 0.0472 (16) | 0.0376 (14) | −0.0232 (13) | 0.0006 (11) | −0.0037 (12) |
C12 | 0.0421 (15) | 0.0378 (14) | 0.0324 (13) | −0.0196 (12) | −0.0033 (11) | −0.0030 (11) |
C13 | 0.0323 (14) | 0.0393 (15) | 0.0400 (14) | −0.0166 (12) | −0.0087 (11) | −0.0018 (11) |
C14 | 0.0259 (12) | 0.0343 (13) | 0.0404 (14) | −0.0141 (11) | −0.0028 (10) | −0.0018 (11) |
C15 | 0.0589 (19) | 0.0524 (18) | 0.0290 (13) | −0.0212 (15) | −0.0048 (13) | 0.0003 (12) |
S1 | 0.0378 (4) | 0.0421 (4) | 0.0414 (4) | −0.0162 (3) | −0.0124 (3) | 0.0064 (3) |
O2 | 0.0700 (16) | 0.0632 (15) | 0.0739 (16) | −0.0123 (12) | −0.0391 (13) | −0.0141 (13) |
O3 | 0.0766 (18) | 0.107 (2) | 0.123 (2) | −0.0605 (17) | −0.0576 (17) | 0.0789 (19) |
O4 | 0.0407 (13) | 0.0874 (18) | 0.0582 (14) | −0.0007 (12) | −0.0066 (11) | −0.0024 (13) |
C16 | 0.0347 (14) | 0.0336 (13) | 0.0356 (13) | −0.0153 (11) | −0.0083 (11) | 0.0016 (11) |
C17 | 0.0374 (15) | 0.0477 (16) | 0.0351 (13) | −0.0188 (13) | −0.0024 (11) | −0.0002 (12) |
C18 | 0.0485 (17) | 0.0498 (17) | 0.0343 (13) | −0.0233 (14) | −0.0081 (12) | 0.0050 (12) |
C19 | 0.0398 (16) | 0.0369 (15) | 0.0476 (15) | −0.0120 (12) | −0.0141 (12) | −0.0003 (12) |
C20 | 0.0333 (15) | 0.0470 (17) | 0.0572 (17) | −0.0169 (13) | −0.0050 (13) | 0.0036 (14) |
C21 | 0.0405 (15) | 0.0421 (15) | 0.0415 (14) | −0.0187 (13) | −0.0025 (12) | 0.0048 (12) |
C22 | 0.054 (2) | 0.059 (2) | 0.076 (2) | −0.0191 (17) | −0.0309 (18) | 0.0104 (18) |
O1—C12 | 1.339 (3) | C12—C13 | 1.389 (4) |
O1—H1A | 0.86 (5) | C13—C14 | 1.367 (4) |
N1—C2 | 1.335 (4) | C13—H13A | 0.9400 |
N1—C6 | 1.344 (3) | C14—H14A | 0.9400 |
N1—C15 | 1.473 (3) | C15—H15A | 0.9700 |
N2—C1 | 1.144 (3) | C15—H15B | 0.9700 |
C1—C7 | 1.441 (3) | C15—H15C | 0.9700 |
C2—C3 | 1.360 (4) | S1—O3 | 1.410 (2) |
C2—H2A | 0.9400 | S1—O4 | 1.436 (2) |
C3—C4 | 1.386 (4) | S1—O2 | 1.452 (2) |
C3—H3A | 0.9400 | S1—C16 | 1.767 (3) |
C4—C5 | 1.405 (4) | C16—C17 | 1.376 (4) |
C4—C7 | 1.460 (3) | C16—C21 | 1.378 (4) |
C5—C6 | 1.352 (4) | C17—C18 | 1.379 (4) |
C5—H5A | 0.9400 | C17—H17A | 0.9400 |
C6—H6A | 0.9400 | C18—C19 | 1.375 (4) |
C7—C8 | 1.355 (3) | C18—H18A | 0.9400 |
C8—C9 | 1.440 (3) | C19—C20 | 1.386 (4) |
C8—H8A | 0.9400 | C19—C22 | 1.500 (4) |
C9—C14 | 1.403 (3) | C20—C21 | 1.385 (4) |
C9—C10 | 1.403 (3) | C20—H20A | 0.9400 |
C10—C11 | 1.364 (4) | C21—H21A | 0.9400 |
C10—H10A | 0.9400 | C22—H22A | 0.9700 |
C11—C12 | 1.391 (4) | C22—H22B | 0.9700 |
C11—H11A | 0.9400 | C22—H22C | 0.9700 |
C12—O1—H1A | 110 (3) | C12—C13—H13A | 120.1 |
C2—N1—C6 | 119.9 (2) | C13—C14—C9 | 122.0 (2) |
C2—N1—C15 | 119.9 (2) | C13—C14—H14A | 119.0 |
C6—N1—C15 | 120.2 (2) | C9—C14—H14A | 119.0 |
N2—C1—C7 | 177.1 (3) | N1—C15—H15A | 109.5 |
N1—C2—C3 | 120.9 (2) | N1—C15—H15B | 109.5 |
N1—C2—H2A | 119.5 | H15A—C15—H15B | 109.5 |
C3—C2—H2A | 119.5 | N1—C15—H15C | 109.5 |
C2—C3—C4 | 121.3 (2) | H15A—C15—H15C | 109.5 |
C2—C3—H3A | 119.3 | H15B—C15—H15C | 109.5 |
C4—C3—H3A | 119.3 | O3—S1—O4 | 114.4 (2) |
C3—C4—C5 | 116.0 (2) | O3—S1—O2 | 112.5 (2) |
C3—C4—C7 | 122.1 (2) | O4—S1—O2 | 110.10 (17) |
C5—C4—C7 | 121.9 (2) | O3—S1—C16 | 107.81 (13) |
C6—C5—C4 | 120.7 (2) | O4—S1—C16 | 106.81 (13) |
C6—C5—H5A | 119.7 | O2—S1—C16 | 104.52 (13) |
C4—C5—H5A | 119.7 | C17—C16—C21 | 120.2 (2) |
N1—C6—C5 | 121.2 (2) | C17—C16—S1 | 119.9 (2) |
N1—C6—H6A | 119.4 | C21—C16—S1 | 119.9 (2) |
C5—C6—H6A | 119.4 | C16—C17—C18 | 119.9 (3) |
C8—C7—C1 | 121.7 (2) | C16—C17—H17A | 120.0 |
C8—C7—C4 | 123.4 (2) | C18—C17—H17A | 120.0 |
C1—C7—C4 | 114.8 (2) | C19—C18—C17 | 121.2 (2) |
C7—C8—C9 | 132.5 (2) | C19—C18—H18A | 119.4 |
C7—C8—H8A | 113.7 | C17—C18—H18A | 119.4 |
C9—C8—H8A | 113.7 | C18—C19—C20 | 118.2 (3) |
C14—C9—C10 | 117.0 (2) | C18—C19—C22 | 121.6 (3) |
C14—C9—C8 | 116.8 (2) | C20—C19—C22 | 120.2 (3) |
C10—C9—C8 | 126.1 (2) | C21—C20—C19 | 121.4 (3) |
C11—C10—C9 | 121.1 (2) | C21—C20—H20A | 119.3 |
C11—C10—H10A | 119.4 | C19—C20—H20A | 119.3 |
C9—C10—H10A | 119.4 | C16—C21—C20 | 119.1 (3) |
C10—C11—C12 | 120.8 (2) | C16—C21—H21A | 120.4 |
C10—C11—H11A | 119.6 | C20—C21—H21A | 120.4 |
C12—C11—H11A | 119.6 | C19—C22—H22A | 109.5 |
O1—C12—C13 | 123.5 (2) | C19—C22—H22B | 109.5 |
O1—C12—C11 | 117.4 (2) | H22A—C22—H22B | 109.5 |
C13—C12—C11 | 119.1 (2) | C19—C22—H22C | 109.5 |
C14—C13—C12 | 119.9 (2) | H22A—C22—H22C | 109.5 |
C14—C13—H13A | 120.1 | H22B—C22—H22C | 109.5 |
C6—N1—C2—C3 | −0.8 (4) | C10—C11—C12—C13 | −0.8 (4) |
C15—N1—C2—C3 | 178.9 (3) | O1—C12—C13—C14 | −179.6 (3) |
N1—C2—C3—C4 | 0.1 (4) | C11—C12—C13—C14 | 1.5 (4) |
C2—C3—C4—C5 | 0.7 (4) | C12—C13—C14—C9 | −0.7 (4) |
C2—C3—C4—C7 | −178.1 (2) | C10—C9—C14—C13 | −1.0 (4) |
C3—C4—C5—C6 | −0.8 (4) | C8—C9—C14—C13 | −179.5 (2) |
C7—C4—C5—C6 | 177.9 (2) | O3—S1—C16—C17 | −150.1 (3) |
C2—N1—C6—C5 | 0.7 (4) | O4—S1—C16—C17 | −26.7 (3) |
C15—N1—C6—C5 | −179.0 (3) | O2—S1—C16—C17 | 90.0 (3) |
C4—C5—C6—N1 | 0.2 (4) | O3—S1—C16—C21 | 32.5 (3) |
C3—C4—C7—C8 | −171.6 (2) | O4—S1—C16—C21 | 155.9 (2) |
C5—C4—C7—C8 | 9.7 (4) | O2—S1—C16—C21 | −87.4 (2) |
C3—C4—C7—C1 | 10.3 (4) | C21—C16—C17—C18 | 0.6 (4) |
C5—C4—C7—C1 | −168.4 (2) | S1—C16—C17—C18 | −176.9 (2) |
C1—C7—C8—C9 | −2.5 (4) | C16—C17—C18—C19 | 0.2 (4) |
C4—C7—C8—C9 | 179.5 (2) | C17—C18—C19—C20 | −1.0 (4) |
C7—C8—C9—C14 | 177.7 (3) | C17—C18—C19—C22 | 179.0 (3) |
C7—C8—C9—C10 | −0.7 (5) | C18—C19—C20—C21 | 1.0 (5) |
C14—C9—C10—C11 | 1.7 (4) | C22—C19—C20—C21 | −178.9 (3) |
C8—C9—C10—C11 | −179.8 (2) | C17—C16—C21—C20 | −0.6 (4) |
C9—C10—C11—C12 | −0.9 (4) | S1—C16—C21—C20 | 176.9 (2) |
C10—C11—C12—O1 | −179.7 (3) | C19—C20—C21—C16 | −0.2 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O2 | 0.86 (5) | 1.73 (5) | 2.578 (3) | 167 (3) |
C5—H5A···N2i | 0.94 | 2.52 | 3.454 (4) | 172 |
C6—H6A···O3ii | 0.94 | 2.30 | 3.039 (4) | 136 |
C21—H21A···O1i | 0.94 | 2.39 | 3.248 (4) | 151 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y, −z+1. |