Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680500930X/at6001sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680500930X/at6001Isup2.hkl |
CCDC reference: 270226
Data collection: COLLECT (Bruker–Nonius, 2002); cell refinement: EVALCCD (Bruker–Nonius, 2002); data reduction: EVALCCD; program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL.
C20H25NS2 | F(000) = 736 |
Mr = 343.53 | Dx = 1.262 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 264 reflections |
a = 9.9686 (8) Å | θ = 6.0–20.0° |
b = 12.2843 (8) Å | µ = 0.29 mm−1 |
c = 14.7707 (3) Å | T = 100 K |
V = 1808.8 (2) Å3 | Block, colourless |
Z = 4 | 0.30 × 0.28 × 0.23 mm |
Nonius KappaCCD diffractometer | 4306 independent reflections |
Radiation source: fine-focus sealed tube | 3828 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.050 |
Detector resolution: 9 pixels mm-1 | θmax = 27.9°, θmin = 3.2° |
ω scans | h = −13→13 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | k = −16→16 |
Tmin = 0.916, Tmax = 0.935 | l = −19→19 |
27385 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.031 | Only H-atom coordinates refined |
wR(F2) = 0.070 | w = 1/[σ2(Fo2) + (0.039P)2 + 0.201P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
4306 reflections | Δρmax = 0.23 e Å−3 |
283 parameters | Δρmin = −0.21 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 1856 Freidel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.02 (5) |
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 | 0.15976 (4) | 0.68713 (3) | 0.01800 (3) | 0.01436 (10) | |
S2 | −0.11815 (4) | 0.65353 (3) | 0.08574 (3) | 0.01770 (11) | |
N1 | 0.11752 (14) | 0.58259 (10) | 0.16288 (9) | 0.0101 (3) | |
C1 | 0.44514 (18) | 0.19189 (14) | 0.11652 (11) | 0.0166 (4) | |
C2 | 0.4973 (2) | 0.11228 (15) | 0.05902 (12) | 0.0192 (4) | |
C3 | 0.62952 (19) | 0.11879 (14) | 0.03051 (12) | 0.0188 (4) | |
C4 | 0.70939 (18) | 0.20476 (15) | 0.05863 (11) | 0.0176 (4) | |
C5 | 0.65786 (18) | 0.28444 (14) | 0.11541 (11) | 0.0152 (4) | |
C6 | 0.52396 (17) | 0.27913 (13) | 0.14524 (11) | 0.0117 (3) | |
C7 | 0.47087 (16) | 0.36513 (13) | 0.20865 (11) | 0.0121 (3) | |
C8 | 0.52228 (19) | 0.34469 (17) | 0.30462 (12) | 0.0179 (4) | |
C9 | 0.48996 (17) | 0.48595 (14) | 0.17840 (12) | 0.0132 (3) | |
C10 | 0.31703 (17) | 0.38502 (14) | 0.20951 (12) | 0.0133 (3) | |
C11 | 0.34450 (17) | 0.51059 (13) | 0.20972 (11) | 0.0112 (3) | |
C12 | 0.25767 (16) | 0.57763 (13) | 0.14866 (11) | 0.0103 (3) | |
C13 | 0.29573 (17) | 0.63181 (13) | 0.07376 (11) | 0.0128 (3) | |
C14 | 0.04775 (17) | 0.63528 (13) | 0.09680 (11) | 0.0133 (3) | |
C15 | 0.05573 (17) | 0.53817 (13) | 0.24697 (11) | 0.0114 (3) | |
C16 | −0.00798 (19) | 0.62749 (14) | 0.30485 (12) | 0.0156 (4) | |
C17 | −0.0537 (2) | 0.57754 (16) | 0.39491 (13) | 0.0207 (4) | |
C18 | −0.1497 (2) | 0.48230 (15) | 0.37902 (14) | 0.0235 (4) | |
C19 | −0.08497 (18) | 0.39573 (15) | 0.31933 (13) | 0.0191 (4) | |
C20 | −0.03935 (19) | 0.44332 (14) | 0.22870 (12) | 0.0161 (4) | |
H1 | 0.348 (2) | 0.1830 (19) | 0.1421 (15) | 0.040* | |
H2 | 0.443 (2) | 0.052 (2) | 0.0419 (16) | 0.040* | |
H3 | 0.664 (2) | 0.0652 (19) | −0.0092 (17) | 0.040* | |
H4 | 0.795 (3) | 0.214 (2) | 0.0379 (16) | 0.040* | |
H5 | 0.712 (2) | 0.346 (2) | 0.1360 (16) | 0.040* | |
H8A | 0.481 (2) | 0.399 (2) | 0.3464 (17) | 0.040* | |
H8B | 0.619 (3) | 0.3418 (19) | 0.3058 (15) | 0.040* | |
H8C | 0.492 (2) | 0.273 (2) | 0.3297 (16) | 0.040* | |
H9A | 0.498 (2) | 0.4902 (19) | 0.1122 (17) | 0.040* | |
H9B | 0.563 (2) | 0.527 (2) | 0.2108 (15) | 0.040* | |
H10A | 0.268 (2) | 0.357 (2) | 0.2625 (17) | 0.040* | |
H10B | 0.270 (2) | 0.363 (2) | 0.1546 (17) | 0.040* | |
H11 | 0.345 (2) | 0.5446 (18) | 0.2735 (16) | 0.040* | |
H13 | 0.383 (3) | 0.6400 (19) | 0.0477 (15) | 0.040* | |
H15 | 0.133 (3) | 0.505 (2) | 0.2786 (16) | 0.040* | |
H16A | 0.063 (2) | 0.685 (2) | 0.3177 (15) | 0.040* | |
H16B | −0.086 (2) | 0.657 (2) | 0.2728 (16) | 0.040* | |
H17A | −0.092 (2) | 0.636 (2) | 0.4335 (16) | 0.040* | |
H17B | 0.022 (3) | 0.554 (2) | 0.4261 (17) | 0.040* | |
H18A | −0.175 (3) | 0.4497 (19) | 0.4348 (17) | 0.040* | |
H18B | −0.233 (2) | 0.511 (2) | 0.3472 (17) | 0.040* | |
H19A | −0.006 (3) | 0.363 (2) | 0.3497 (16) | 0.040* | |
H19B | −0.149 (2) | 0.3312 (19) | 0.3059 (15) | 0.040* | |
H20A | −0.117 (3) | 0.471 (2) | 0.1941 (15) | 0.040* | |
H20B | 0.002 (3) | 0.385 (2) | 0.1922 (16) | 0.040* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0176 (2) | 0.01383 (19) | 0.01165 (18) | −0.00148 (16) | −0.00226 (16) | 0.00350 (16) |
S2 | 0.0130 (2) | 0.0172 (2) | 0.0230 (2) | 0.00020 (16) | −0.00675 (17) | 0.00499 (19) |
N1 | 0.0113 (6) | 0.0088 (6) | 0.0102 (6) | −0.0007 (5) | −0.0007 (5) | 0.0013 (5) |
C1 | 0.0190 (9) | 0.0129 (8) | 0.0178 (8) | 0.0019 (7) | 0.0013 (7) | 0.0022 (7) |
C2 | 0.0262 (10) | 0.0119 (8) | 0.0197 (9) | −0.0001 (8) | −0.0019 (8) | −0.0011 (7) |
C3 | 0.0296 (10) | 0.0146 (8) | 0.0123 (8) | 0.0073 (7) | 0.0020 (7) | 0.0002 (7) |
C4 | 0.0169 (9) | 0.0230 (9) | 0.0129 (8) | 0.0039 (8) | 0.0039 (7) | 0.0035 (8) |
C5 | 0.0140 (8) | 0.0166 (8) | 0.0148 (8) | 0.0008 (7) | −0.0013 (7) | −0.0004 (7) |
C6 | 0.0131 (8) | 0.0125 (8) | 0.0097 (7) | 0.0028 (6) | −0.0011 (6) | 0.0017 (6) |
C7 | 0.0113 (8) | 0.0113 (8) | 0.0138 (8) | 0.0017 (6) | −0.0006 (6) | 0.0008 (6) |
C8 | 0.0177 (9) | 0.0228 (9) | 0.0132 (8) | 0.0063 (8) | −0.0011 (7) | −0.0006 (8) |
C9 | 0.0105 (8) | 0.0118 (8) | 0.0174 (8) | 0.0012 (7) | −0.0002 (7) | 0.0001 (7) |
C10 | 0.0120 (8) | 0.0118 (8) | 0.0160 (8) | 0.0015 (7) | 0.0014 (7) | 0.0018 (7) |
C11 | 0.0092 (8) | 0.0123 (8) | 0.0122 (7) | −0.0003 (6) | −0.0009 (6) | −0.0001 (6) |
C12 | 0.0097 (8) | 0.0093 (8) | 0.0120 (8) | −0.0018 (6) | −0.0008 (6) | −0.0018 (6) |
C13 | 0.0129 (8) | 0.0125 (8) | 0.0131 (8) | −0.0007 (6) | −0.0007 (6) | 0.0000 (7) |
C14 | 0.0167 (8) | 0.0090 (7) | 0.0142 (8) | −0.0021 (6) | −0.0021 (7) | −0.0013 (7) |
C15 | 0.0102 (8) | 0.0123 (8) | 0.0117 (8) | −0.0015 (6) | 0.0012 (6) | 0.0037 (7) |
C16 | 0.0184 (9) | 0.0127 (9) | 0.0157 (8) | 0.0020 (7) | 0.0019 (7) | 0.0003 (7) |
C17 | 0.0228 (10) | 0.0206 (9) | 0.0188 (9) | 0.0037 (8) | 0.0075 (8) | 0.0000 (8) |
C18 | 0.0218 (10) | 0.0218 (9) | 0.0270 (10) | 0.0015 (8) | 0.0110 (8) | 0.0057 (8) |
C19 | 0.0167 (9) | 0.0138 (8) | 0.0270 (10) | 0.0004 (7) | 0.0061 (8) | 0.0048 (8) |
C20 | 0.0171 (10) | 0.0098 (8) | 0.0213 (9) | 0.0006 (7) | 0.0015 (7) | 0.0028 (7) |
S1—C13 | 1.725 (2) | C9—H9B | 1.01 (3) |
S1—C14 | 1.734 (2) | C10—C11 | 1.567 (2) |
S2—C14 | 1.677 (2) | C10—H10A | 0.98 (2) |
N1—C14 | 1.362 (2) | C10—H10B | 0.97 (3) |
N1—C12 | 1.414 (2) | C11—C12 | 1.497 (2) |
N1—C15 | 1.490 (2) | C11—H11 | 1.03 (2) |
C1—C6 | 1.395 (2) | C12—C13 | 1.346 (2) |
C1—C2 | 1.396 (3) | C13—H13 | 0.96 (3) |
C1—H1 | 1.05 (2) | C15—C20 | 1.526 (2) |
C2—C3 | 1.386 (3) | C15—C16 | 1.529 (2) |
C2—H2 | 0.95 (3) | C15—H15 | 0.98 (3) |
C3—C4 | 1.386 (3) | C16—C17 | 1.534 (2) |
C3—H3 | 0.95 (3) | C16—H16A | 1.02 (3) |
C4—C5 | 1.388 (2) | C16—H16B | 0.98 (2) |
C4—H4 | 0.91 (2) | C17—C18 | 1.530 (3) |
C5—C6 | 1.407 (2) | C17—H17A | 1.00 (3) |
C5—H5 | 0.98 (2) | C17—H17B | 0.93 (3) |
C6—C7 | 1.508 (2) | C18—C19 | 1.525 (3) |
C7—C8 | 1.528 (2) | C18—H18A | 0.95 (2) |
C7—C10 | 1.553 (2) | C18—H18B | 1.01 (3) |
C7—C9 | 1.562 (2) | C19—C20 | 1.530 (3) |
C8—H8A | 0.99 (3) | C19—H19A | 1.00 (3) |
C8—H8B | 0.96 (2) | C19—H19B | 1.04 (2) |
C8—H8C | 1.00 (3) | C20—H20A | 0.99 (3) |
C9—C11 | 1.552 (2) | C20—H20B | 0.98 (3) |
C9—H9A | 0.98 (2) | ||
C13—S1—C14 | 92.34 (8) | C12—C11—H11 | 109.2 (13) |
C14—N1—C12 | 114.74 (14) | C9—C11—H11 | 110.5 (14) |
C14—N1—C15 | 124.08 (14) | C10—C11—H11 | 113.6 (13) |
C12—N1—C15 | 121.09 (13) | C13—C12—N1 | 112.29 (15) |
C6—C1—C2 | 120.89 (17) | C13—C12—C11 | 127.19 (15) |
C6—C1—H1 | 119.5 (13) | N1—C12—C11 | 120.36 (14) |
C2—C1—H1 | 119.5 (13) | C12—C13—S1 | 111.5 (1) |
C3—C2—C1 | 119.92 (17) | C12—C13—H13 | 129.7 (14) |
C3—C2—H2 | 120.4 (15) | S1—C13—H13 | 118.7 (14) |
C1—C2—H2 | 119.6 (15) | N1—C14—S2 | 129.6 (1) |
C2—C3—C4 | 119.94 (17) | N1—C14—S1 | 109.1 (1) |
C2—C3—H3 | 119.8 (15) | S2—C14—S1 | 121.4 (1) |
C4—C3—H3 | 120.3 (15) | N1—C15—C20 | 112.90 (14) |
C3—C4—C5 | 120.39 (17) | N1—C15—C16 | 112.02 (13) |
C3—C4—H4 | 122.2 (16) | C20—C15—C16 | 112.87 (14) |
C5—C4—H4 | 117.3 (16) | N1—C15—H15 | 102.9 (14) |
C4—C5—C6 | 120.51 (16) | C20—C15—H15 | 104.9 (14) |
C4—C5—H5 | 122.2 (14) | C16—C15—H15 | 110.5 (14) |
C6—C5—H5 | 117.3 (14) | C15—C16—C17 | 108.74 (14) |
C1—C6—C5 | 118.34 (16) | C15—C16—H16A | 108.3 (13) |
C1—C6—C7 | 121.97 (15) | C17—C16—H16A | 108.9 (13) |
C5—C6—C7 | 119.66 (15) | C15—C16—H16B | 109.1 (14) |
C6—C7—C8 | 110.09 (13) | C17—C16—H16B | 109.6 (14) |
C6—C7—C10 | 117.51 (14) | H16A—C16—H16B | 112.2 (19) |
C8—C7—C10 | 110.45 (14) | C18—C17—C16 | 111.02 (16) |
C6—C7—C9 | 116.45 (14) | C18—C17—H17A | 113.7 (13) |
C8—C7—C9 | 112.38 (14) | C16—C17—H17A | 108.7 (13) |
C10—C7—C9 | 88.47 (12) | C18—C17—H17B | 110.3 (15) |
C7—C8—H8A | 109.2 (14) | C16—C17—H17B | 108.2 (15) |
C7—C8—H8B | 111.0 (13) | H17A—C17—H17B | 105 (2) |
H8A—C8—H8B | 115 (2) | C19—C18—C17 | 110.94 (15) |
C7—C8—H8C | 112.8 (14) | C19—C18—H18A | 108.6 (15) |
H8A—C8—H8C | 103.3 (19) | C17—C18—H18A | 110.7 (14) |
H8B—C8—H8C | 105 (2) | C19—C18—H18B | 108.5 (14) |
C11—C9—C7 | 89.21 (12) | C17—C18—H18B | 108.7 (14) |
C11—C9—H9A | 111.5 (14) | H18A—C18—H18B | 109 (2) |
C7—C9—H9A | 110.2 (14) | C18—C19—C20 | 111.42 (15) |
C11—C9—H9B | 115.7 (13) | C18—C19—H19A | 111.0 (14) |
C7—C9—H9B | 115.6 (14) | C20—C19—H19A | 108.2 (14) |
H9A—C9—H9B | 112.6 (19) | C18—C19—H19B | 112.7 (13) |
C7—C10—C11 | 88.99 (12) | C20—C19—H19B | 107.9 (13) |
C7—C10—H10A | 116.3 (14) | H19A—C19—H19B | 105.4 (18) |
C11—C10—H10A | 115.4 (15) | C15—C20—C19 | 108.77 (15) |
C7—C10—H10B | 115.0 (14) | C15—C20—H20A | 108.5 (15) |
C11—C10—H10B | 111.0 (15) | C19—C20—H20A | 110.5 (14) |
H10A—C10—H10B | 109.1 (19) | C15—C20—H20B | 113.1 (15) |
C12—C11—C9 | 117.91 (14) | C19—C20—H20B | 109.1 (14) |
C12—C11—C10 | 116.07 (14) | H20A—C20—H20B | 107 (2) |
C9—C11—C10 | 88.32 (12) |