Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806048355/kp2062sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806048355/kp2062Isup2.hkl |
CCDC reference: 630042
Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1993); 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: SHELXL97 and WinGX (Farrugia, 1999).
C13H15N3O3S | Dx = 1.494 Mg m−3 |
Mr = 293.34 | Melting point = 506–508 K |
Orthorhombic, Pbca | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 223 reflections |
a = 11.142 (2) Å | θ = 12.1–79.4° |
b = 14.929 (3) Å | µ = 2.33 mm−1 |
c = 15.680 (3) Å | T = 293 K |
V = 2608.2 (9) Å3 | Prism, colourless |
Z = 8 | 0.25 × 0.20 × 0.20 mm |
F(000) = 1232 |
Bruker SMART APEX CCD diffractometer | 2478 independent reflections |
Radiation source: fine-focus sealed tube | 2437 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
ω scans | θmax = 70.1°, θmin = 5.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | h = −13→13 |
Tmin = 0.588, Tmax = 0.654 | k = −18→17 |
27602 measured reflections | l = −19→19 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.033 | Only H-atom coordinates refined |
wR(F2) = 0.097 | w = 1/[σ2(Fo2) + (0.0623P)2 + 0.6394P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
2478 reflections | Δρmax = 0.32 e Å−3 |
227 parameters | Δρmin = −0.26 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00073 (13) |
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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) - 6.7527 (0.0052) x + 0.2850 (0.0080) y + 12.4686 (0.0059) z = 1.7797 (0.0007) * 0.0114 (0.0010) C5 * 0.0079 (0.0010) C6 * -0.0192 (0.0009) C7 * 0.0097 (0.0009) N8 * 0.0106 (0.0009) C9 * -0.0203 (0.0009) C10 0.0388 (0.0028) C15 - 0.1150 (0.0025) C16 Rms deviation of fitted atoms = 0.0140 - 4.1551 (0.0204) x - 0.3216 (0.0183) y + 14.5449 (0.0115) z = 1.7341 (0.0022) Angle to previous plane (with approximate e.s.d.) = 15.59 (0.16) * 0.0292 (0.0006) C10 * -0.0250 (0.0005) C4 * -0.0382 (0.0008) C3 * 0.0340 (0.0007) C11 - 0.0217 (0.0042) O4 - 0.1643 (0.0044) N2 - 0.0232 (0.0041) C21 Rms deviation of fitted atoms = 0.0320 |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.12118 (3) | 0.05327 (2) | 0.21629 (2) | 0.03978 (15) | |
O1S | 0.06360 (11) | 0.07823 (8) | 0.29436 (7) | 0.0533 (3) | |
O2S | 0.22613 (10) | −0.00200 (7) | 0.22148 (8) | 0.0557 (3) | |
O4 | −0.14085 (10) | 0.20694 (7) | 0.08207 (9) | 0.0585 (3) | |
N2 | 0.15304 (11) | 0.13765 (8) | 0.15469 (8) | 0.0430 (3) | |
N8 | 0.01101 (10) | −0.08456 (7) | 0.15140 (7) | 0.0392 (3) | |
N12 | 0.17698 (13) | 0.31775 (9) | 0.18528 (9) | 0.0501 (3) | |
H121 | 0.192 (2) | 0.3727 (15) | 0.1915 (15) | 0.075* | |
C3 | 0.05537 (13) | 0.19807 (9) | 0.13680 (9) | 0.0401 (3) | |
C4 | −0.05521 (12) | 0.16057 (9) | 0.10529 (9) | 0.0407 (3) | |
C5 | −0.15850 (12) | 0.01562 (9) | 0.05745 (9) | 0.0399 (3) | |
C6 | −0.15806 (13) | −0.07752 (10) | 0.05954 (9) | 0.0422 (3) | |
H61 | −0.2131 (18) | −0.1065 (13) | 0.0279 (13) | 0.063* | |
C7 | −0.07353 (12) | −0.12614 (9) | 0.10425 (9) | 0.0392 (3) | |
C9 | 0.01042 (12) | 0.00401 (9) | 0.14913 (9) | 0.0359 (3) | |
C10 | −0.06713 (12) | 0.05990 (9) | 0.10338 (9) | 0.0364 (3) | |
C11 | 0.07534 (14) | 0.28903 (9) | 0.14948 (9) | 0.0430 (3) | |
C13 | 0.27362 (16) | 0.25930 (12) | 0.21222 (11) | 0.0517 (4) | |
H131 | 0.263 (2) | 0.2391 (17) | 0.2726 (14) | 0.078* | |
H132 | 0.347 (2) | 0.2963 (16) | 0.2053 (14) | 0.078* | |
C14 | 0.27384 (14) | 0.17758 (11) | 0.15540 (11) | 0.0492 (4) | |
H141 | 0.292 (2) | 0.1941 (14) | 0.0969 (14) | 0.074* | |
H142 | 0.329 (2) | 0.1333 (15) | 0.1757 (14) | 0.074* | |
C15 | −0.25437 (17) | 0.06139 (12) | 0.00668 (13) | 0.0561 (4) | |
H151 | −0.292 (2) | 0.0176 (15) | −0.0302 (15) | 0.084* | |
H152 | −0.221 (2) | 0.1067 (16) | −0.0274 (16) | 0.084* | |
H153 | −0.309 (2) | 0.0878 (16) | 0.0437 (16) | 0.084* | |
C16 | −0.06932 (15) | −0.22622 (10) | 0.10114 (12) | 0.0487 (4) | |
H161 | −0.0518 (19) | −0.2505 (14) | 0.1557 (14) | 0.073* | |
H162 | −0.008 (2) | −0.2435 (14) | 0.0664 (15) | 0.073* | |
H163 | −0.142 (2) | −0.2488 (15) | 0.0823 (14) | 0.073* | |
C21 | −0.01002 (18) | 0.36087 (10) | 0.12275 (12) | 0.0538 (4) | |
H211 | −0.025 (2) | 0.3590 (15) | 0.0640 (16) | 0.081* | |
H212 | −0.087 (2) | 0.3547 (15) | 0.1510 (15) | 0.081* | |
H213 | 0.021 (2) | 0.4180 (17) | 0.1380 (14) | 0.081* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0410 (2) | 0.0283 (2) | 0.0500 (2) | −0.00044 (12) | −0.00860 (13) | −0.00348 (12) |
O1S | 0.0691 (8) | 0.0432 (6) | 0.0477 (6) | −0.0041 (5) | −0.0038 (5) | −0.0048 (5) |
O2S | 0.0479 (6) | 0.0369 (5) | 0.0823 (8) | 0.0062 (5) | −0.0209 (5) | −0.0074 (5) |
O4 | 0.0456 (6) | 0.0398 (6) | 0.0901 (9) | 0.0089 (5) | −0.0090 (6) | 0.0013 (6) |
N2 | 0.0358 (6) | 0.0335 (6) | 0.0598 (7) | −0.0039 (5) | −0.0025 (5) | −0.0011 (5) |
N8 | 0.0402 (6) | 0.0312 (6) | 0.0462 (6) | −0.0034 (4) | −0.0029 (5) | −0.0011 (5) |
N12 | 0.0625 (8) | 0.0346 (6) | 0.0531 (7) | −0.0127 (6) | 0.0046 (6) | −0.0040 (5) |
C3 | 0.0420 (7) | 0.0306 (6) | 0.0478 (7) | −0.0004 (5) | 0.0022 (6) | 0.0014 (5) |
C4 | 0.0395 (7) | 0.0332 (7) | 0.0493 (8) | 0.0026 (5) | 0.0030 (6) | 0.0005 (5) |
C5 | 0.0361 (7) | 0.0420 (7) | 0.0415 (7) | 0.0012 (6) | 0.0009 (5) | −0.0022 (6) |
C6 | 0.0388 (7) | 0.0415 (7) | 0.0462 (7) | −0.0059 (6) | −0.0024 (6) | −0.0074 (6) |
C7 | 0.0393 (7) | 0.0346 (7) | 0.0438 (7) | −0.0054 (5) | 0.0030 (5) | −0.0034 (5) |
C9 | 0.0345 (6) | 0.0311 (6) | 0.0422 (7) | −0.0027 (5) | −0.0007 (5) | −0.0029 (5) |
C10 | 0.0342 (7) | 0.0333 (7) | 0.0418 (7) | 0.0003 (5) | 0.0034 (5) | −0.0018 (5) |
C11 | 0.0540 (8) | 0.0332 (7) | 0.0417 (7) | −0.0049 (6) | 0.0092 (6) | 0.0006 (5) |
C13 | 0.0497 (9) | 0.0495 (9) | 0.0560 (9) | −0.0168 (7) | 0.0002 (7) | −0.0052 (7) |
C14 | 0.0379 (8) | 0.0481 (8) | 0.0615 (9) | −0.0092 (6) | 0.0012 (7) | −0.0071 (7) |
C15 | 0.0510 (9) | 0.0530 (9) | 0.0642 (10) | 0.0072 (7) | −0.0180 (8) | −0.0057 (8) |
C16 | 0.0495 (9) | 0.0343 (7) | 0.0622 (10) | −0.0082 (6) | −0.0021 (7) | −0.0042 (7) |
C21 | 0.0697 (11) | 0.0309 (7) | 0.0608 (10) | 0.0025 (7) | 0.0103 (8) | 0.0032 (7) |
S1—O1S | 1.4314 (12) | C6—H61 | 0.90 (2) |
S1—O2S | 1.4334 (11) | C7—C16 | 1.4955 (19) |
S1—N2 | 1.6266 (13) | C9—C10 | 1.3990 (19) |
S1—C9 | 1.7813 (13) | C11—C21 | 1.494 (2) |
O4—C4 | 1.2338 (18) | C13—C14 | 1.511 (2) |
N2—C3 | 1.4411 (18) | C13—H131 | 1.00 (2) |
N2—C14 | 1.4721 (18) | C13—H132 | 1.00 (2) |
N8—C9 | 1.3228 (18) | C14—H141 | 0.97 (2) |
N8—C7 | 1.3487 (17) | C14—H142 | 0.96 (2) |
N12—C11 | 1.335 (2) | C15—H151 | 0.97 (2) |
N12—C13 | 1.449 (2) | C15—H152 | 0.94 (3) |
N12—H121 | 0.84 (2) | C15—H153 | 0.93 (3) |
C3—C11 | 1.3902 (19) | C16—H161 | 0.95 (2) |
C3—C4 | 1.441 (2) | C16—H162 | 0.91 (2) |
C4—C10 | 1.5090 (19) | C16—H163 | 0.92 (2) |
C5—C6 | 1.391 (2) | C21—H211 | 0.94 (2) |
C5—C10 | 1.4114 (19) | C21—H212 | 0.97 (2) |
C5—C15 | 1.497 (2) | C21—H213 | 0.95 (2) |
C6—C7 | 1.380 (2) | ||
O1S—S1—O2S | 117.84 (7) | N12—C11—C3 | 120.64 (14) |
O1S—S1—N2 | 113.83 (7) | N12—C11—C21 | 115.32 (13) |
O2S—S1—N2 | 107.55 (7) | C3—C11—C21 | 124.01 (15) |
O1S—S1—C9 | 107.61 (7) | N12—C13—C14 | 108.39 (13) |
O2S—S1—C9 | 111.17 (7) | N12—C13—H131 | 111.8 (14) |
N2—S1—C9 | 96.88 (6) | C14—C13—H131 | 108.4 (14) |
C3—N2—C14 | 116.00 (12) | N12—C13—H132 | 104.3 (13) |
C3—N2—S1 | 115.83 (10) | C14—C13—H132 | 112.5 (13) |
C14—N2—S1 | 120.58 (11) | H131—C13—H132 | 111.4 (19) |
C9—N8—C7 | 116.23 (11) | N2—C14—C13 | 109.27 (13) |
C11—N12—C13 | 124.04 (12) | N2—C14—H141 | 106.6 (13) |
C11—N12—H121 | 122.2 (16) | C13—C14—H141 | 110.7 (13) |
C13—N12—H121 | 113.6 (16) | N2—C14—H142 | 108.2 (13) |
C11—C3—C4 | 124.44 (13) | C13—C14—H142 | 111.2 (13) |
C11—C3—N2 | 117.56 (13) | H141—C14—H142 | 110.7 (19) |
C4—C3—N2 | 117.99 (12) | C5—C15—H151 | 108.7 (14) |
O4—C4—C3 | 122.99 (13) | C5—C15—H152 | 110.4 (15) |
O4—C4—C10 | 119.01 (13) | H151—C15—H152 | 108.6 (19) |
C3—C4—C10 | 117.98 (12) | C5—C15—H153 | 109.4 (15) |
C6—C5—C10 | 116.98 (13) | H151—C15—H153 | 111.6 (19) |
C6—C5—C15 | 118.11 (13) | H152—C15—H153 | 108 (2) |
C10—C5—C15 | 124.90 (13) | C7—C16—H161 | 111.0 (13) |
C7—C6—C5 | 122.68 (13) | C7—C16—H162 | 108.9 (14) |
C7—C6—H61 | 119.5 (12) | H161—C16—H162 | 106.0 (19) |
C5—C6—H61 | 117.7 (12) | C7—C16—H163 | 110.4 (14) |
N8—C7—C6 | 120.85 (13) | H161—C16—H163 | 109.2 (19) |
N8—C7—C16 | 117.12 (13) | H162—C16—H163 | 111.3 (19) |
C6—C7—C16 | 122.01 (13) | C11—C21—H211 | 111.4 (14) |
N8—C9—C10 | 127.81 (12) | C11—C21—H212 | 111.6 (13) |
N8—C9—S1 | 113.16 (10) | H211—C21—H212 | 107.0 (19) |
C10—C9—S1 | 119.00 (10) | C11—C21—H213 | 109.8 (14) |
C9—C10—C5 | 115.32 (12) | H211—C21—H213 | 109.8 (19) |
C9—C10—C4 | 121.97 (12) | H212—C21—H213 | 107.2 (19) |
C5—C10—C4 | 122.69 (12) | ||
O1S—S1—N2—C3 | −51.65 (12) | O1S—S1—C9—C10 | 80.31 (12) |
O2S—S1—N2—C3 | 175.90 (10) | O2S—S1—C9—C10 | −149.28 (11) |
C9—S1—N2—C3 | 61.08 (11) | N2—S1—C9—C10 | −37.41 (12) |
O1S—S1—N2—C14 | 96.74 (12) | N8—C9—C10—C5 | 3.1 (2) |
O2S—S1—N2—C14 | −35.72 (13) | S1—C9—C10—C5 | −174.87 (10) |
C9—S1—N2—C14 | −150.53 (12) | N8—C9—C10—C4 | −178.51 (13) |
C14—N2—C3—C11 | −20.62 (19) | S1—C9—C10—C4 | 3.57 (18) |
S1—N2—C3—C11 | 129.25 (12) | C6—C5—C10—C9 | −2.83 (19) |
C14—N2—C3—C4 | 158.05 (13) | C15—C5—C10—C9 | 177.61 (15) |
S1—N2—C3—C4 | −52.09 (16) | C6—C5—C10—C4 | 178.74 (13) |
C11—C3—C4—O4 | 4.1 (2) | C15—C5—C10—C4 | −0.8 (2) |
N2—C3—C4—O4 | −174.43 (14) | O4—C4—C10—C9 | −162.30 (14) |
C11—C3—C4—C10 | −173.98 (13) | C3—C4—C10—C9 | 15.9 (2) |
N2—C3—C4—C10 | 7.45 (19) | O4—C4—C10—C5 | 16.0 (2) |
C10—C5—C6—C7 | 0.3 (2) | C3—C4—C10—C5 | −165.78 (13) |
C15—C5—C6—C7 | 179.87 (15) | C13—N12—C11—C3 | 1.0 (2) |
C9—N8—C7—C6 | −2.60 (19) | C13—N12—C11—C21 | −177.23 (15) |
C9—N8—C7—C16 | 175.94 (13) | C4—C3—C11—N12 | 174.63 (13) |
C5—C6—C7—N8 | 2.6 (2) | N2—C3—C11—N12 | −6.8 (2) |
C5—C6—C7—C16 | −175.82 (14) | C4—C3—C11—C21 | −7.3 (2) |
C7—N8—C9—C10 | −0.3 (2) | N2—C3—C11—C21 | 171.22 (14) |
C7—N8—C9—S1 | 177.74 (10) | C11—N12—C13—C14 | 29.7 (2) |
O1S—S1—C9—N8 | −97.90 (11) | C3—N2—C14—C13 | 50.78 (19) |
O2S—S1—C9—N8 | 32.51 (13) | S1—N2—C14—C13 | −97.56 (15) |
N2—S1—C9—N8 | 144.37 (10) | N12—C13—C14—N2 | −52.78 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
N12—H121···O2Si | 0.84 (2) | 2.13 (2) | 2.9545 (18) | 165 (2) |
C13—H131···O4ii | 1.00 (2) | 2.56 (2) | 3.453 (2) | 148.0 (17) |
C13—H132···N8i | 1.00 (2) | 2.53 (2) | 3.479 (2) | 160.8 (18) |
C16—H163···O4iii | 0.92 (2) | 2.51 (2) | 3.393 (2) | 160.1 (18) |
Symmetry codes: (i) −x+1/2, y+1/2, z; (ii) x+1/2, y, −z+1/2; (iii) −x−1/2, y−1/2, z. |