Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680602099X/er2004sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680602099X/er20043sup2.hkl |
CCDC reference: 613670
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); software used to prepare material for publication: WinGX (Farrugia, 1999).
C19H18N2S | F(000) = 1296 |
Mr = 306.41 | Dx = 1.274 Mg m−3 |
Monoclinic, C2/c | Cu Kα radiation, λ = 1.54184 Å |
Hall symbol: -C 2yc | Cell parameters from 25 reflections |
a = 18.064 (4) Å | θ = 21.2–42.8° |
b = 7.901 (2) Å | µ = 1.76 mm−1 |
c = 22.401 (7) Å | T = 293 K |
β = 91.76 (2)° | Prism, light brown |
V = 3195.9 (15) Å3 | 0.36 × 0.24 × 0.12 mm |
Z = 8 |
Enraf Nonius TurboCAD-4 diffractometer | Rint = 0.034 |
non–profiled ω scans | θmax = 74.2°, θmin = 4.0° |
Absorption correction: ψ scan (North et al., 1968) | h = −22→0 |
Tmin = 0.632, Tmax = 0.810 | k = 0→9 |
3110 measured reflections | l = −27→27 |
3018 independent reflections | 3 standard reflections every 120 min |
2081 reflections with I > 2σ(I) | intensity decay: none |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.063 | w = 1/[σ2(Fo2) + (0.0984P)2 + 2.0386P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.185 | (Δ/σ)max < 0.001 |
S = 1.06 | Δρmax = 0.59 e Å−3 |
3018 reflections | Δρmin = −0.42 e Å−3 |
199 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 | 0.1297 (2) | 0.9049 (5) | 0.02442 (17) | 0.0671 (10) | |
H2A | 0.1219 | 0.7908 | 0.0095 | 0.08* | |
H2B | 0.0891 | 0.9333 | 0.0499 | 0.08* | |
C3 | 0.13196 (18) | 1.0293 (5) | −0.02786 (15) | 0.0579 (9) | |
H1A | 0.1048 | 0.9851 | −0.0625 | 0.069* | |
H1B | 0.1109 | 1.1376 | −0.0171 | 0.069* | |
C5 | 0.25152 (17) | 1.1083 (4) | −0.08669 (13) | 0.0442 (7) | |
C6 | 0.32483 (16) | 1.0976 (4) | −0.06574 (13) | 0.0440 (7) | |
C7 | 0.25890 (18) | 1.0033 (4) | 0.00440 (13) | 0.0480 (7) | |
C8 | 0.39419 (16) | 1.1459 (4) | −0.09406 (12) | 0.0426 (7) | |
C9 | 0.46018 (17) | 1.0751 (4) | −0.07258 (14) | 0.0498 (8) | |
H14 | 0.4591 | 0.998 | −0.0413 | 0.06* | |
C10 | 0.52726 (18) | 1.1166 (5) | −0.09666 (15) | 0.0539 (8) | |
H15 | 0.5705 | 1.0687 | −0.0807 | 0.065* | |
C11 | 0.53125 (17) | 1.2283 (5) | −0.14404 (15) | 0.0524 (8) | |
C12 | 0.46545 (18) | 1.2979 (5) | −0.16568 (15) | 0.0550 (8) | |
H17 | 0.4666 | 1.373 | −0.1976 | 0.066* | |
C13 | 0.39789 (18) | 1.2591 (4) | −0.14121 (14) | 0.0525 (8) | |
H18 | 0.3548 | 1.3093 | −0.1565 | 0.063* | |
C14 | 0.21589 (16) | 1.1558 (4) | −0.14387 (13) | 0.0435 (7) | |
C15 | 0.24043 (17) | 1.0918 (4) | −0.19792 (13) | 0.0484 (8) | |
H7 | 0.282 | 1.0224 | −0.198 | 0.058* | |
C16 | 0.20376 (18) | 1.1301 (5) | −0.25136 (14) | 0.0530 (8) | |
H8 | 0.2215 | 1.0868 | −0.2868 | 0.064* | |
C17 | 0.14110 (17) | 1.2317 (4) | −0.25328 (14) | 0.0501 (8) | |
C18 | 0.11741 (18) | 1.2976 (5) | −0.19955 (15) | 0.0555 (9) | |
H10 | 0.0759 | 1.3673 | −0.1997 | 0.067* | |
C19 | 0.15398 (18) | 1.2621 (4) | −0.14583 (15) | 0.0538 (8) | |
H11 | 0.1372 | 1.3093 | −0.1107 | 0.065* | |
C20 | 0.1003 (2) | 1.2702 (5) | −0.31163 (16) | 0.0676 (10) | |
H12A | 0.0586 | 1.3418 | −0.3042 | 0.101* | |
H12B | 0.0832 | 1.1664 | −0.3296 | 0.101* | |
H12C | 0.133 | 1.3266 | −0.3381 | 0.101* | |
C21 | 0.6040 (2) | 1.2703 (6) | −0.17189 (18) | 0.0708 (11) | |
H19A | 0.5957 | 1.3494 | −0.2039 | 0.106* | |
H19B | 0.6257 | 1.1688 | −0.1872 | 0.106* | |
H19C | 0.637 | 1.3195 | −0.1423 | 0.106* | |
N4 | 0.21061 (14) | 1.0462 (3) | −0.03994 (11) | 0.0464 (6) | |
N7 | 0.32813 (14) | 1.0307 (4) | −0.00790 (11) | 0.0491 (6) | |
S1 | 0.21703 (5) | 0.91680 (13) | 0.06671 (4) | 0.0628 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C2 | 0.065 (2) | 0.079 (3) | 0.058 (2) | −0.009 (2) | 0.0117 (17) | 0.007 (2) |
C3 | 0.0467 (19) | 0.074 (2) | 0.0529 (18) | −0.0054 (17) | 0.0063 (14) | −0.0019 (17) |
C5 | 0.0464 (16) | 0.0491 (18) | 0.0374 (15) | 0.0034 (14) | 0.0025 (12) | −0.0027 (13) |
C6 | 0.0458 (17) | 0.0496 (18) | 0.0366 (14) | 0.0015 (14) | 0.0011 (12) | −0.0013 (13) |
C7 | 0.0551 (19) | 0.051 (2) | 0.0382 (15) | 0.0015 (15) | 0.0031 (13) | −0.0016 (14) |
C8 | 0.0429 (15) | 0.0490 (17) | 0.0358 (14) | −0.0011 (13) | 0.0010 (12) | −0.0030 (13) |
C9 | 0.0500 (18) | 0.058 (2) | 0.0408 (16) | 0.0020 (15) | −0.0032 (13) | −0.0027 (14) |
C10 | 0.0420 (17) | 0.068 (2) | 0.0514 (18) | 0.0041 (15) | −0.0032 (14) | −0.0068 (16) |
C11 | 0.0435 (17) | 0.060 (2) | 0.0539 (18) | −0.0062 (15) | 0.0060 (14) | −0.0106 (16) |
C12 | 0.0551 (19) | 0.058 (2) | 0.0519 (18) | −0.0023 (16) | 0.0078 (15) | 0.0064 (16) |
C13 | 0.0479 (18) | 0.057 (2) | 0.0523 (18) | 0.0071 (15) | 0.0030 (14) | 0.0035 (16) |
C14 | 0.0411 (15) | 0.0484 (17) | 0.0411 (15) | 0.0004 (13) | 0.0015 (12) | 0.0007 (13) |
C15 | 0.0411 (16) | 0.058 (2) | 0.0462 (17) | 0.0076 (14) | 0.0041 (13) | 0.0000 (15) |
C16 | 0.0515 (18) | 0.068 (2) | 0.0403 (16) | −0.0012 (16) | 0.0057 (13) | 0.0000 (15) |
C17 | 0.0447 (17) | 0.054 (2) | 0.0509 (17) | −0.0080 (15) | −0.0042 (13) | 0.0084 (15) |
C18 | 0.0451 (17) | 0.060 (2) | 0.061 (2) | 0.0100 (16) | −0.0041 (15) | 0.0051 (17) |
C19 | 0.0499 (18) | 0.061 (2) | 0.0511 (18) | 0.0077 (16) | 0.0064 (14) | −0.0050 (16) |
C20 | 0.064 (2) | 0.078 (3) | 0.060 (2) | −0.0080 (19) | −0.0169 (17) | 0.015 (2) |
C21 | 0.054 (2) | 0.080 (3) | 0.079 (3) | −0.0100 (19) | 0.0130 (18) | −0.004 (2) |
N4 | 0.0452 (14) | 0.0520 (15) | 0.0422 (13) | −0.0001 (12) | 0.0058 (10) | −0.0001 (11) |
N7 | 0.0511 (15) | 0.0579 (16) | 0.0383 (13) | 0.0014 (13) | −0.0007 (11) | 0.0008 (12) |
S1 | 0.0678 (6) | 0.0772 (7) | 0.0437 (5) | −0.0071 (5) | 0.0087 (4) | 0.0076 (4) |
C2—C3 | 1.530 (5) | C11—C21 | 1.509 (5) |
C2—S1 | 1.818 (4) | C12—C13 | 1.388 (4) |
C2—H2A | 0.97 | C12—H17 | 0.93 |
C2—H2B | 0.97 | C13—H18 | 0.93 |
C3—N4 | 1.461 (4) | C14—C19 | 1.398 (4) |
C3—H1A | 0.97 | C14—C15 | 1.397 (4) |
C3—H1B | 0.97 | C15—C16 | 1.384 (4) |
C5—N4 | 1.390 (4) | C15—H7 | 0.93 |
C5—C6 | 1.394 (4) | C16—C17 | 1.387 (5) |
C5—C14 | 1.465 (4) | C16—H8 | 0.93 |
C6—N7 | 1.399 (4) | C17—C18 | 1.391 (5) |
C6—C8 | 1.472 (4) | C17—C20 | 1.512 (4) |
C7—N7 | 1.307 (4) | C18—C19 | 1.384 (4) |
C7—N4 | 1.345 (4) | C18—H10 | 0.93 |
C7—S1 | 1.747 (3) | C19—H11 | 0.93 |
C8—C13 | 1.387 (4) | C20—H12A | 0.96 |
C8—C9 | 1.389 (4) | C20—H12B | 0.96 |
C9—C10 | 1.381 (5) | C20—H12C | 0.96 |
C9—H14 | 0.93 | C21—H19A | 0.96 |
C10—C11 | 1.384 (5) | C21—H19B | 0.96 |
C10—H15 | 0.93 | C21—H19C | 0.96 |
C11—C12 | 1.384 (5) | ||
C3—C2—S1 | 108.8 (2) | C12—C13—H18 | 119.8 |
C3—C2—H2A | 109.9 | C8—C13—H18 | 119.8 |
S1—C2—H2A | 109.9 | C19—C14—C15 | 117.7 (3) |
C3—C2—H2B | 109.9 | C19—C14—C5 | 120.7 (3) |
S1—C2—H2B | 109.9 | C15—C14—C5 | 121.5 (3) |
H2A—C2—H2B | 108.3 | C16—C15—C14 | 121.0 (3) |
N4—C3—C2 | 104.5 (3) | C16—C15—H7 | 119.5 |
N4—C3—H1A | 110.9 | C14—C15—H7 | 119.5 |
C2—C3—H1A | 110.9 | C15—C16—C17 | 121.5 (3) |
N4—C3—H1B | 110.9 | C15—C16—H8 | 119.3 |
C2—C3—H1B | 110.9 | C17—C16—H8 | 119.3 |
H1A—C3—H1B | 108.9 | C18—C17—C16 | 117.5 (3) |
N4—C5—C6 | 104.3 (3) | C18—C17—C20 | 121.2 (3) |
N4—C5—C14 | 121.3 (3) | C16—C17—C20 | 121.3 (3) |
C6—C5—C14 | 134.2 (3) | C17—C18—C19 | 121.7 (3) |
C5—C6—N7 | 110.3 (3) | C17—C18—H10 | 119.2 |
C5—C6—C8 | 130.7 (3) | C19—C18—H10 | 119.2 |
N7—C6—C8 | 119.0 (3) | C18—C19—C14 | 120.6 (3) |
N7—C7—N4 | 113.9 (3) | C18—C19—H11 | 119.7 |
N7—C7—S1 | 132.4 (3) | C14—C19—H11 | 119.7 |
N4—C7—S1 | 113.7 (2) | C17—C20—H12A | 109.5 |
C13—C8—C9 | 117.5 (3) | C17—C20—H12B | 109.5 |
C13—C8—C6 | 123.8 (3) | H12A—C20—H12B | 109.5 |
C9—C8—C6 | 118.6 (3) | C17—C20—H12C | 109.5 |
C10—C9—C8 | 121.5 (3) | H12A—C20—H12C | 109.5 |
C10—C9—H14 | 119.2 | H12B—C20—H12C | 109.5 |
C8—C9—H14 | 119.2 | C11—C21—H19A | 109.5 |
C9—C10—C11 | 121.2 (3) | C11—C21—H19B | 109.5 |
C9—C10—H15 | 119.4 | H19A—C21—H19B | 109.5 |
C11—C10—H15 | 119.4 | C11—C21—H19C | 109.5 |
C10—C11—C12 | 117.2 (3) | H19A—C21—H19C | 109.5 |
C10—C11—C21 | 121.6 (3) | H19B—C21—H19C | 109.5 |
C12—C11—C21 | 121.2 (3) | C7—N4—C5 | 107.3 (3) |
C13—C12—C11 | 122.0 (3) | C7—N4—C3 | 116.9 (3) |
C13—C12—H17 | 119 | C5—N4—C3 | 135.6 (3) |
C11—C12—H17 | 119 | C7—N7—C6 | 104.1 (3) |
C12—C13—C8 | 120.5 (3) | C7—S1—C2 | 89.66 (16) |
S1—C2—C3—N4 | 26.2 (3) | C14—C15—C16—C17 | −0.7 (5) |
N4—C5—C6—N7 | 0.1 (3) | C15—C16—C17—C18 | 1.6 (5) |
C14—C5—C6—N7 | −175.0 (3) | C15—C16—C17—C20 | −178.7 (3) |
N4—C5—C6—C8 | −179.1 (3) | C16—C17—C18—C19 | −0.9 (5) |
C14—C5—C6—C8 | 5.8 (6) | C20—C17—C18—C19 | 179.4 (3) |
C5—C6—C8—C13 | 20.4 (5) | C17—C18—C19—C14 | −0.9 (5) |
N7—C6—C8—C13 | −158.8 (3) | C15—C14—C19—C18 | 1.9 (5) |
C5—C6—C8—C9 | −159.8 (3) | C5—C14—C19—C18 | −175.6 (3) |
N7—C6—C8—C9 | 21.0 (4) | N7—C7—N4—C5 | 0.1 (4) |
C13—C8—C9—C10 | 0.7 (5) | S1—C7—N4—C5 | −178.4 (2) |
C6—C8—C9—C10 | −179.2 (3) | N7—C7—N4—C3 | −176.2 (3) |
C8—C9—C10—C11 | −1.3 (5) | S1—C7—N4—C3 | 5.3 (4) |
C9—C10—C11—C12 | 0.8 (5) | C6—C5—N4—C7 | −0.1 (3) |
C9—C10—C11—C21 | −178.1 (3) | C14—C5—N4—C7 | 175.8 (3) |
C10—C11—C12—C13 | 0.2 (5) | C6—C5—N4—C3 | 175.1 (3) |
C21—C11—C12—C13 | 179.1 (3) | C14—C5—N4—C3 | −9.0 (6) |
C11—C12—C13—C8 | −0.8 (5) | C2—C3—N4—C7 | −20.6 (4) |
C9—C8—C13—C12 | 0.4 (5) | C2—C3—N4—C5 | 164.4 (3) |
C6—C8—C13—C12 | −179.8 (3) | N4—C7—N7—C6 | −0.1 (4) |
N4—C5—C14—C19 | 49.8 (5) | S1—C7—N7—C6 | 178.1 (3) |
C6—C5—C14—C19 | −135.7 (4) | C5—C6—N7—C7 | 0.0 (3) |
N4—C5—C14—C15 | −127.6 (3) | C8—C6—N7—C7 | 179.3 (3) |
C6—C5—C14—C15 | 46.9 (5) | N7—C7—S1—C2 | −168.4 (4) |
C19—C14—C15—C16 | −1.1 (5) | N4—C7—S1—C2 | 9.9 (3) |
C5—C14—C15—C16 | 176.3 (3) | C3—C2—S1—C7 | −21.1 (3) |