Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806013808/cf2014sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806013808/cf2014IIsup2.hkl |
CCDC reference: 608583
Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and Mercury (Bruno et al., 2002); software used to prepare material for publication: SHELXTL.
C20H24N2O3S | Dx = 1.288 Mg m−3 |
Mr = 372.47 | Melting point = 419–422 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 903 reflections |
a = 8.134 (2) Å | θ = 2.7–25.7° |
b = 11.043 (3) Å | µ = 0.19 mm−1 |
c = 21.385 (6) Å | T = 293 K |
V = 1920.9 (9) Å3 | Block, yellow |
Z = 4 | 0.30 × 0.24 × 0.22 mm |
F(000) = 792 |
Bruker SMART APEX CCD area-detector diffractometer | 3717 independent reflections |
Radiation source: sealed tube | 2909 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.049 |
φ and ω scans | θmax = 26.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −6→9 |
Tmin = 0.952, Tmax = 0.963 | k = −13→11 |
10001 measured reflections | l = −25→26 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.055 | H-atom parameters constrained |
wR(F2) = 0.123 | w = 1/[σ2(Fo2) + (0.06P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
3717 reflections | Δρmax = 0.26 e Å−3 |
236 parameters | Δρmin = −0.39 e Å−3 |
0 restraints | Absolute structure: Flack (1983), with how many Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.26 (11) |
Experimental. Spectroscopic data for (II). 1H NMR (300 MHz CDCl3) 12.55 (s, 1H), 8.17 (s, 1H), 7.56–7.52 (m, 2H), 7.28–7.26 (m, 1H), 7.05–6.77 (m, 5H), 5.10 (m, 1H), 3.24–3.21 (m, 1H), 2.98–2.90 (m, 1H), 2.28–2.23 (m, 4H), 1.81–1.75 (m, 3H), 1.59–1.52 (m, 1H), 1.38–1.31 (m, 3H); 13C NMR (75 MHz CDCl3) p.p.m. 165.5, 161.3, 143.4, 137.8, 132.5, 131.9, 129.9, 126.9, 118.9, 118.8, 117.1, 72.5, 57.7, 34.0, 24.9, 24.0, 21.9; ESI (MS) m/z: 373.3 (M+). |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.5825 (4) | 1.0327 (3) | 0.04421 (12) | 0.0417 (7) | |
H1 | 0.6531 | 0.9608 | 0.0439 | 0.050* | |
C2 | 0.6870 (5) | 1.1457 (3) | 0.03194 (16) | 0.0573 (9) | |
H2A | 0.6199 | 1.2174 | 0.0379 | 0.069* | |
H2B | 0.7765 | 1.1486 | 0.0618 | 0.069* | |
C3 | 0.7562 (4) | 1.1458 (3) | −0.03345 (17) | 0.0565 (9) | |
H3A | 0.8211 | 1.2184 | −0.0398 | 0.068* | |
H3B | 0.8277 | 1.0763 | −0.0388 | 0.068* | |
C4 | 0.6226 (4) | 1.1413 (3) | −0.08027 (16) | 0.0593 (10) | |
H4A | 0.6688 | 1.1428 | −0.1221 | 0.071* | |
H4B | 0.5517 | 1.2113 | −0.0755 | 0.071* | |
C5 | 0.5219 (5) | 1.0238 (3) | −0.07086 (13) | 0.0531 (9) | |
H5A | 0.4335 | 1.0208 | −0.1012 | 0.064* | |
H5B | 0.5922 | 0.9541 | −0.0776 | 0.064* | |
C6 | 0.4499 (4) | 1.0192 (3) | −0.00443 (12) | 0.0374 (6) | |
H6 | 0.3714 | 1.0859 | 0.0004 | 0.045* | |
C7 | 0.5479 (4) | 0.9770 (3) | 0.14964 (13) | 0.0431 (7) | |
H7 | 0.6221 | 0.9150 | 0.1413 | 0.052* | |
C8 | 0.4838 (4) | 0.9910 (3) | 0.21380 (13) | 0.0463 (7) | |
C9 | 0.3662 (4) | 1.0787 (3) | 0.22781 (14) | 0.0499 (8) | |
C10 | 0.3130 (5) | 1.0928 (4) | 0.28967 (16) | 0.0704 (11) | |
H10 | 0.2375 | 1.1530 | 0.2997 | 0.084* | |
C11 | 0.3730 (6) | 1.0170 (5) | 0.33589 (18) | 0.0826 (14) | |
H11 | 0.3363 | 1.0254 | 0.3769 | 0.099* | |
C12 | 0.4853 (6) | 0.9303 (4) | 0.32152 (15) | 0.0734 (12) | |
H12 | 0.5270 | 0.8814 | 0.3532 | 0.088* | |
C13 | 0.5396 (5) | 0.9131 (4) | 0.26018 (15) | 0.0593 (9) | |
H13 | 0.6119 | 0.8506 | 0.2506 | 0.071* | |
C14 | 0.1674 (4) | 0.8482 (3) | 0.10262 (14) | 0.0433 (7) | |
C15 | 0.0614 (5) | 0.9045 (3) | 0.14196 (16) | 0.0613 (9) | |
H15 | −0.0023 | 0.9691 | 0.1282 | 0.074* | |
C16 | 0.0498 (5) | 0.8630 (4) | 0.20421 (17) | 0.0627 (10) | |
H16 | −0.0216 | 0.9018 | 0.2316 | 0.075* | |
C17 | 0.1411 (5) | 0.7669 (3) | 0.22527 (17) | 0.0597 (9) | |
C18 | 0.2485 (5) | 0.7115 (3) | 0.18346 (16) | 0.0550 (8) | |
H18 | 0.3119 | 0.6463 | 0.1967 | 0.066* | |
C19 | 0.2625 (4) | 0.7516 (3) | 0.12285 (15) | 0.0505 (8) | |
H19 | 0.3354 | 0.7141 | 0.0955 | 0.061* | |
N1 | 0.5055 (3) | 1.0458 (2) | 0.10634 (11) | 0.0447 (6) | |
N2 | 0.3606 (3) | 0.9035 (2) | 0.00238 (11) | 0.0473 (6) | |
H2 | 0.4141 | 0.8381 | −0.0055 | 0.057* | |
O1 | 0.3064 (3) | 1.1537 (2) | 0.18368 (12) | 0.0642 (7) | |
H1A | 0.3849 | 1.1595 | 0.1503 | 0.096* | |
O2 | 0.0979 (3) | 1.0045 (2) | 0.01574 (13) | 0.0690 (7) | |
O3 | 0.1128 (4) | 0.7882 (2) | −0.01073 (12) | 0.0748 (8) | |
C20 | 0.1252 (6) | 0.7199 (4) | 0.28958 (17) | 0.0821 (14) | |
H20E | 0.0246 | 0.7038 | 0.2965 | 0.099* | |
H20C | 0.1585 | 0.7728 | 0.3155 | 0.099* | |
H20D | 0.1829 | 0.6564 | 0.2944 | 0.099* | |
S1 | 0.17423 (10) | 0.88992 (7) | 0.02299 (4) | 0.0473 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0542 (18) | 0.0408 (15) | 0.0300 (13) | 0.0035 (14) | 0.0010 (13) | −0.0010 (12) |
C2 | 0.064 (2) | 0.0575 (19) | 0.0500 (19) | −0.0104 (17) | −0.0087 (18) | −0.0050 (15) |
C3 | 0.0450 (16) | 0.069 (2) | 0.056 (2) | −0.0059 (16) | 0.0028 (16) | 0.0051 (17) |
C4 | 0.055 (2) | 0.072 (2) | 0.051 (2) | −0.0071 (17) | 0.0078 (16) | 0.0279 (17) |
C5 | 0.058 (2) | 0.076 (2) | 0.0261 (14) | −0.0093 (19) | −0.0010 (14) | 0.0079 (14) |
C6 | 0.0401 (15) | 0.0414 (13) | 0.0306 (13) | 0.0002 (12) | 0.0031 (11) | 0.0066 (11) |
C7 | 0.0517 (18) | 0.0456 (16) | 0.0320 (13) | 0.0037 (15) | −0.0064 (13) | −0.0027 (13) |
C8 | 0.061 (2) | 0.0481 (17) | 0.0301 (13) | −0.0046 (15) | −0.0024 (14) | −0.0015 (12) |
C9 | 0.050 (2) | 0.062 (2) | 0.0371 (15) | −0.0060 (16) | 0.0038 (13) | −0.0080 (14) |
C10 | 0.068 (2) | 0.102 (3) | 0.0416 (18) | −0.011 (2) | 0.0099 (18) | −0.0100 (19) |
C11 | 0.079 (3) | 0.128 (4) | 0.040 (2) | −0.025 (3) | 0.0131 (19) | −0.007 (2) |
C12 | 0.077 (3) | 0.113 (3) | 0.0303 (17) | −0.016 (3) | −0.0065 (18) | 0.0211 (19) |
C13 | 0.066 (2) | 0.076 (2) | 0.0360 (15) | −0.003 (2) | −0.0056 (16) | 0.0100 (15) |
C14 | 0.0514 (16) | 0.0430 (15) | 0.0356 (14) | −0.0045 (15) | −0.0005 (15) | 0.0030 (12) |
C15 | 0.067 (2) | 0.058 (2) | 0.059 (2) | 0.0094 (19) | 0.0160 (18) | 0.0161 (16) |
C16 | 0.067 (2) | 0.072 (2) | 0.0492 (19) | 0.0121 (19) | 0.0278 (18) | 0.0046 (16) |
C17 | 0.065 (3) | 0.060 (2) | 0.054 (2) | −0.0158 (18) | 0.0073 (17) | 0.0152 (17) |
C18 | 0.066 (2) | 0.0496 (19) | 0.0496 (19) | 0.0059 (17) | 0.0006 (17) | 0.0083 (15) |
C19 | 0.058 (2) | 0.052 (2) | 0.0416 (17) | 0.0086 (16) | −0.0102 (14) | 0.0026 (14) |
N1 | 0.0552 (16) | 0.0476 (14) | 0.0312 (12) | −0.0002 (12) | −0.0006 (12) | −0.0025 (11) |
N2 | 0.0501 (16) | 0.0493 (13) | 0.0426 (13) | −0.0082 (12) | −0.0083 (11) | 0.0102 (11) |
O1 | 0.0790 (18) | 0.0645 (15) | 0.0490 (13) | 0.0170 (14) | 0.0029 (13) | −0.0011 (11) |
O2 | 0.0632 (14) | 0.0701 (15) | 0.0736 (17) | 0.0022 (12) | 0.0032 (13) | 0.0379 (14) |
O3 | 0.100 (2) | 0.0766 (17) | 0.0473 (15) | −0.0408 (16) | −0.0108 (13) | 0.0125 (11) |
C20 | 0.099 (4) | 0.102 (3) | 0.045 (2) | −0.020 (3) | 0.012 (2) | 0.010 (2) |
S1 | 0.0501 (4) | 0.0493 (4) | 0.0426 (4) | −0.0082 (4) | −0.0083 (4) | 0.0102 (3) |
C1—N1 | 1.476 (4) | C10—H10 | 0.930 |
C1—C6 | 1.506 (4) | C11—C12 | 1.358 (6) |
C1—C2 | 1.532 (4) | C11—H11 | 0.930 |
C1—H1 | 0.980 | C12—C13 | 1.397 (5) |
C2—C3 | 1.507 (5) | C12—H12 | 0.930 |
C2—H2A | 0.970 | C13—H13 | 0.930 |
C2—H2B | 0.970 | C14—C15 | 1.356 (5) |
C3—C4 | 1.478 (5) | C14—C19 | 1.386 (4) |
C3—H3A | 0.970 | C14—S1 | 1.765 (3) |
C3—H3B | 0.970 | C15—C16 | 1.411 (5) |
C4—C5 | 1.547 (5) | C15—H15 | 0.930 |
C4—H4A | 0.970 | C16—C17 | 1.371 (5) |
C4—H4B | 0.970 | C16—H16 | 0.930 |
C5—C6 | 1.538 (4) | C17—C18 | 1.392 (5) |
C5—H5A | 0.970 | C17—C20 | 1.476 (5) |
C5—H5B | 0.970 | C18—C19 | 1.374 (4) |
C6—N2 | 1.477 (4) | C18—H18 | 0.930 |
C6—H6 | 0.980 | C19—H19 | 0.930 |
C7—N1 | 1.247 (4) | N2—S1 | 1.586 (3) |
C7—C8 | 1.476 (4) | N2—H2 | 0.860 |
C7—H7 | 0.930 | O1—H1A | 0.960 |
C8—C13 | 1.389 (4) | O2—S1 | 1.418 (3) |
C8—C9 | 1.394 (5) | O3—S1 | 1.425 (3) |
C9—O1 | 1.346 (4) | C20—H20E | 0.850 |
C9—C10 | 1.400 (4) | C20—H20C | 0.850 |
C10—C11 | 1.385 (7) | C20—H20D | 0.850 |
N1—C1—C6 | 109.1 (3) | C11—C10—H10 | 120.1 |
N1—C1—C2 | 108.0 (2) | C9—C10—H10 | 120.1 |
C6—C1—C2 | 111.1 (2) | C12—C11—C10 | 120.1 (4) |
N1—C1—H1 | 109.5 | C12—C11—H11 | 119.9 |
C6—C1—H1 | 109.5 | C10—C11—H11 | 119.9 |
C2—C1—H1 | 109.5 | C11—C12—C13 | 121.4 (4) |
C3—C2—C1 | 111.5 (3) | C11—C12—H12 | 119.3 |
C3—C2—H2A | 109.3 | C13—C12—H12 | 119.3 |
C1—C2—H2A | 109.3 | C8—C13—C12 | 118.9 (4) |
C3—C2—H2B | 109.3 | C8—C13—H13 | 120.6 |
C1—C2—H2B | 109.3 | C12—C13—H13 | 120.6 |
H2A—C2—H2B | 108.0 | C15—C14—C19 | 120.9 (3) |
C4—C3—C2 | 110.7 (3) | C15—C14—S1 | 119.9 (3) |
C4—C3—H3A | 109.5 | C19—C14—S1 | 119.0 (2) |
C2—C3—H3A | 109.5 | C14—C15—C16 | 118.6 (3) |
C4—C3—H3B | 109.5 | C14—C15—H15 | 120.7 |
C2—C3—H3B | 109.5 | C16—C15—H15 | 120.7 |
H3A—C3—H3B | 108.1 | C17—C16—C15 | 121.7 (3) |
C3—C4—C5 | 109.2 (3) | C17—C16—H16 | 119.2 |
C3—C4—H4A | 109.8 | C15—C16—H16 | 119.2 |
C5—C4—H4A | 109.8 | C16—C17—C18 | 118.0 (3) |
C3—C4—H4B | 109.8 | C16—C17—C20 | 122.1 (4) |
C5—C4—H4B | 109.8 | C18—C17—C20 | 119.9 (4) |
H4A—C4—H4B | 108.3 | C19—C18—C17 | 121.1 (3) |
C6—C5—C4 | 110.5 (3) | C19—C18—H18 | 119.5 |
C6—C5—H5A | 109.6 | C17—C18—H18 | 119.5 |
C4—C5—H5A | 109.6 | C18—C19—C14 | 119.8 (3) |
C6—C5—H5B | 109.6 | C18—C19—H19 | 120.1 |
C4—C5—H5B | 109.6 | C14—C19—H19 | 120.1 |
H5A—C5—H5B | 108.1 | C7—N1—C1 | 119.4 (3) |
N2—C6—C1 | 111.7 (2) | C6—N2—S1 | 125.4 (2) |
N2—C6—C5 | 107.9 (2) | C6—N2—H2 | 117.3 |
C1—C6—C5 | 111.2 (3) | S1—N2—H2 | 117.3 |
N2—C6—H6 | 108.6 | C9—O1—H1A | 108.8 |
C1—C6—H6 | 108.6 | C17—C20—H20E | 108.6 |
C5—C6—H6 | 108.6 | C17—C20—H20C | 109.8 |
N1—C7—C8 | 121.9 (3) | H20E—C20—H20C | 109.8 |
N1—C7—H7 | 119.0 | C17—C20—H20D | 110.7 |
C8—C7—H7 | 119.0 | H20E—C20—H20D | 109.7 |
C13—C8—C9 | 120.1 (3) | H20C—C20—H20D | 108.2 |
C13—C8—C7 | 118.9 (3) | O2—S1—O3 | 119.61 (17) |
C9—C8—C7 | 121.0 (3) | O2—S1—N2 | 107.69 (15) |
O1—C9—C8 | 121.6 (3) | O3—S1—N2 | 105.62 (16) |
O1—C9—C10 | 118.8 (3) | O2—S1—C14 | 108.96 (16) |
C8—C9—C10 | 119.5 (3) | O3—S1—C14 | 105.75 (14) |
C11—C10—C9 | 119.9 (4) | N2—S1—C14 | 108.83 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···N1 | 0.96 | 1.85 | 2.603 (4) | 133 |
C3—H3B···O2i | 0.97 | 2.61 | 3.357 (5) | 134 |
N2—H2···O3ii | 0.86 | 2.16 | 2.953 (4) | 153 |
C13—H13···O1iii | 0.93 | 2.67 | 3.349 (5) | 130 |
Symmetry codes: (i) x+1, y, z; (ii) x+1/2, −y+3/2, −z; (iii) −x+1, y−1/2, −z+1/2. |