Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806002819/hk2003sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806002819/hk2003Isup2.hkl |
CCDC reference: 298463
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: DIRDIF99 (Beurskens et al., 1999); 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).
C21H19NS2 | F(000) = 736 |
Mr = 349.49 | Dx = 1.283 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 9.7960 (7) Å | θ = 5.6–13.7° |
b = 17.1416 (16) Å | µ = 0.30 mm−1 |
c = 11.2536 (14) Å | T = 297 K |
β = 106.699 (8)° | Plate, yellow |
V = 1810.0 (3) Å3 | 0.50 × 0.50 × 0.23 mm |
Z = 4 |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.045 |
non–profiled ω/2θ scans | θmax = 27.5°, θmin = 2.2° |
Absorption correction: ψ scan (North et al., 1968) | h = −12→12 |
Tmin = 0.784, Tmax = 0.931 | k = 0→22 |
4362 measured reflections | l = 0→14 |
4154 independent reflections | 3 standard reflections every 120 min |
2629 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)] = 0.043 | w = 1/[σ2(Fo2) + (0.0823P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.149 | (Δ/σ)max < 0.001 |
S = 1.10 | Δρmax = 0.44 e Å−3 |
4154 reflections | Δρmin = −0.32 e Å−3 |
217 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 | ||
S2 | 0.14888 (7) | 0.01713 (3) | 0.32152 (7) | 0.0565 (2) | |
S1 | 0.31832 (8) | 0.37154 (4) | 0.14512 (6) | 0.0618 (2) | |
N | 0.14846 (19) | 0.26240 (10) | 0.24171 (18) | 0.0441 (4) | |
C16 | 0.0200 (2) | 0.05986 (12) | 0.1948 (2) | 0.0431 (5) | |
C2 | 0.3342 (2) | 0.36076 (11) | 0.3037 (2) | 0.0418 (5) | |
C21 | 0.1808 (3) | −0.11917 (13) | 0.4433 (2) | 0.0496 (6) | |
C15 | −0.0849 (2) | 0.01618 (13) | 0.1119 (2) | 0.0525 (6) | |
H15 | −0.092 | −0.037 | 0.1254 | 0.063* | |
C12 | −0.0689 (2) | 0.17371 (13) | 0.0705 (2) | 0.0505 (6) | |
H12 | −0.0642 | 0.2269 | 0.0558 | 0.061* | |
C6 | 0.2453 (3) | 0.30037 (13) | 0.4611 (2) | 0.0497 (6) | |
H6 | 0.1816 | 0.267 | 0.4829 | 0.06* | |
C10 | 0.1288 (2) | 0.19093 (12) | 0.2632 (2) | 0.0437 (5) | |
H10 | 0.1813 | 0.1695 | 0.3383 | 0.052* | |
C7 | 0.2429 (2) | 0.30657 (11) | 0.3375 (2) | 0.0403 (5) | |
C14 | −0.1782 (3) | 0.05059 (15) | 0.0106 (3) | 0.0579 (7) | |
H14 | −0.2472 | 0.0204 | −0.0441 | 0.069* | |
C3 | 0.4314 (3) | 0.40135 (12) | 0.3971 (2) | 0.0511 (6) | |
H3 | 0.4947 | 0.4356 | 0.3766 | 0.061* | |
C11 | 0.0273 (2) | 0.14123 (12) | 0.1747 (2) | 0.0417 (5) | |
C20 | 0.0813 (3) | −0.08046 (13) | 0.3328 (3) | 0.0564 (6) | |
H20A | −0.0138 | −0.0777 | 0.3426 | 0.068* | |
H20B | 0.0769 | −0.1099 | 0.2582 | 0.068* | |
C24 | 0.3673 (3) | −0.19226 (17) | 0.6466 (3) | 0.0698 (8) | |
H24 | 0.4298 | −0.2164 | 0.7147 | 0.084* | |
C5 | 0.3409 (3) | 0.34295 (14) | 0.5519 (2) | 0.0573 (6) | |
H5 | 0.3411 | 0.3385 | 0.6344 | 0.069* | |
C22 | 0.3023 (3) | −0.15707 (14) | 0.4328 (3) | 0.0587 (6) | |
H22 | 0.3218 | −0.1581 | 0.3566 | 0.07* | |
C23 | 0.3946 (3) | −0.19324 (16) | 0.5342 (3) | 0.0698 (8) | |
H23 | 0.4756 | −0.2183 | 0.526 | 0.084* | |
C26 | 0.1560 (3) | −0.11897 (15) | 0.5572 (3) | 0.0622 (7) | |
H26 | 0.0757 | −0.0936 | 0.5665 | 0.075* | |
C13 | −0.1707 (3) | 0.12955 (15) | −0.0113 (2) | 0.0574 (6) | |
H13 | −0.2337 | 0.1525 | −0.0805 | 0.069* | |
C4 | 0.4361 (3) | 0.39206 (14) | 0.5200 (3) | 0.0571 (6) | |
H4 | 0.5036 | 0.419 | 0.5814 | 0.068* | |
C25 | 0.2475 (4) | −0.15565 (18) | 0.6587 (3) | 0.0708 (8) | |
H25 | 0.2279 | −0.1555 | 0.7348 | 0.085* | |
C1 | 0.4201 (3) | 0.45838 (16) | 0.1414 (3) | 0.0695 (8) | |
H1A | 0.4177 | 0.4697 | 0.0573 | 0.104* | |
H1B | 0.517 | 0.4505 | 0.1903 | 0.104* | |
H1C | 0.3799 | 0.5013 | 0.1747 | 0.104* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S2 | 0.0508 (4) | 0.0326 (3) | 0.0746 (4) | −0.0057 (2) | −0.0001 (3) | 0.0057 (3) |
S1 | 0.0752 (5) | 0.0533 (4) | 0.0602 (4) | −0.0213 (3) | 0.0247 (3) | −0.0034 (3) |
N | 0.0410 (10) | 0.0313 (9) | 0.0595 (12) | −0.0054 (7) | 0.0138 (8) | 0.0011 (8) |
C16 | 0.0356 (11) | 0.0328 (10) | 0.0610 (14) | −0.0006 (8) | 0.0142 (10) | 0.0007 (9) |
C2 | 0.0393 (11) | 0.0263 (9) | 0.0601 (13) | 0.0011 (8) | 0.0150 (10) | 0.0010 (9) |
C21 | 0.0507 (13) | 0.0303 (10) | 0.0693 (16) | −0.0037 (9) | 0.0195 (12) | 0.0019 (10) |
C15 | 0.0432 (12) | 0.0368 (11) | 0.0726 (17) | −0.0034 (10) | 0.0087 (11) | −0.0022 (11) |
C12 | 0.0459 (12) | 0.0387 (12) | 0.0673 (15) | −0.0012 (10) | 0.0167 (11) | 0.0051 (11) |
C6 | 0.0501 (13) | 0.0378 (11) | 0.0654 (16) | 0.0009 (10) | 0.0233 (12) | 0.0027 (10) |
C10 | 0.0396 (11) | 0.0336 (10) | 0.0583 (13) | −0.0001 (9) | 0.0147 (10) | 0.0022 (10) |
C7 | 0.0364 (10) | 0.0286 (9) | 0.0564 (13) | 0.0043 (8) | 0.0144 (9) | 0.0021 (9) |
C14 | 0.0424 (12) | 0.0498 (13) | 0.0740 (17) | −0.0058 (11) | 0.0047 (12) | −0.0083 (12) |
C3 | 0.0448 (12) | 0.0369 (11) | 0.0701 (17) | −0.0080 (10) | 0.0140 (11) | −0.0026 (11) |
C11 | 0.0369 (10) | 0.0325 (10) | 0.0578 (13) | −0.0017 (8) | 0.0172 (10) | 0.0007 (9) |
C20 | 0.0561 (14) | 0.0339 (11) | 0.0752 (17) | −0.0066 (10) | 0.0125 (12) | 0.0061 (11) |
C24 | 0.0664 (17) | 0.0590 (16) | 0.076 (2) | −0.0015 (14) | 0.0076 (15) | 0.0118 (14) |
C5 | 0.0684 (16) | 0.0494 (13) | 0.0539 (14) | 0.0055 (12) | 0.0170 (12) | −0.0007 (11) |
C22 | 0.0644 (16) | 0.0463 (13) | 0.0726 (17) | 0.0049 (12) | 0.0309 (14) | 0.0053 (12) |
C23 | 0.0560 (16) | 0.0564 (15) | 0.099 (2) | 0.0142 (13) | 0.0253 (16) | 0.0109 (15) |
C26 | 0.0609 (16) | 0.0543 (15) | 0.0788 (19) | 0.0025 (12) | 0.0320 (14) | −0.0016 (14) |
C13 | 0.0470 (13) | 0.0541 (14) | 0.0644 (16) | 0.0026 (11) | 0.0051 (12) | 0.0053 (12) |
C4 | 0.0573 (15) | 0.0440 (13) | 0.0629 (17) | −0.0027 (11) | 0.0060 (12) | −0.0071 (11) |
C25 | 0.084 (2) | 0.0702 (18) | 0.0636 (17) | −0.0055 (16) | 0.0291 (15) | 0.0038 (15) |
C1 | 0.0712 (18) | 0.0582 (16) | 0.0815 (19) | −0.0123 (14) | 0.0258 (15) | 0.0182 (14) |
S2—C16 | 1.769 (2) | C14—C13 | 1.381 (3) |
S2—C20 | 1.817 (2) | C14—H14 | 0.93 |
S1—C2 | 1.756 (2) | C3—C4 | 1.380 (4) |
S1—C1 | 1.799 (3) | C3—H3 | 0.93 |
N—C10 | 1.274 (3) | C20—H20A | 0.97 |
N—C7 | 1.420 (3) | C20—H20B | 0.97 |
C16—C15 | 1.391 (3) | C24—C23 | 1.365 (4) |
C16—C11 | 1.418 (3) | C24—C25 | 1.371 (4) |
C2—C3 | 1.386 (3) | C24—H24 | 0.93 |
C2—C7 | 1.415 (3) | C5—C4 | 1.378 (4) |
C21—C26 | 1.372 (4) | C5—H5 | 0.93 |
C21—C22 | 1.391 (3) | C22—C23 | 1.383 (4) |
C21—C20 | 1.496 (3) | C22—H22 | 0.93 |
C15—C14 | 1.373 (3) | C23—H23 | 0.93 |
C15—H15 | 0.93 | C26—C25 | 1.384 (4) |
C12—C13 | 1.374 (3) | C26—H26 | 0.93 |
C12—C11 | 1.393 (3) | C13—H13 | 0.93 |
C12—H12 | 0.93 | C4—H4 | 0.93 |
C6—C5 | 1.380 (3) | C25—H25 | 0.93 |
C6—C7 | 1.388 (3) | C1—H1A | 0.96 |
C6—H6 | 0.93 | C1—H1B | 0.96 |
C10—C11 | 1.462 (3) | C1—H1C | 0.96 |
C10—H10 | 0.93 | ||
C16—S2—C20 | 104.34 (11) | C21—C20—S2 | 107.65 (16) |
C2—S1—C1 | 102.87 (13) | C21—C20—H20A | 110.2 |
C10—N—C7 | 118.00 (19) | S2—C20—H20A | 110.2 |
C15—C16—C11 | 119.0 (2) | C21—C20—H20B | 110.2 |
C15—C16—S2 | 122.42 (17) | S2—C20—H20B | 110.2 |
C11—C16—S2 | 118.58 (16) | H20A—C20—H20B | 108.5 |
C3—C2—C7 | 118.4 (2) | C23—C24—C25 | 119.9 (3) |
C3—C2—S1 | 123.98 (18) | C23—C24—H24 | 120 |
C7—C2—S1 | 117.63 (17) | C25—C24—H24 | 120 |
C26—C21—C22 | 117.8 (2) | C4—C5—C6 | 119.7 (2) |
C26—C21—C20 | 121.8 (2) | C4—C5—H5 | 120.1 |
C22—C21—C20 | 120.4 (2) | C6—C5—H5 | 120.1 |
C14—C15—C16 | 120.8 (2) | C23—C22—C21 | 120.8 (3) |
C14—C15—H15 | 119.6 | C23—C22—H22 | 119.6 |
C16—C15—H15 | 119.6 | C21—C22—H22 | 119.6 |
C13—C12—C11 | 122.0 (2) | C24—C23—C22 | 120.2 (3) |
C13—C12—H12 | 119 | C24—C23—H23 | 119.9 |
C11—C12—H12 | 119 | C22—C23—H23 | 119.9 |
C5—C6—C7 | 121.0 (2) | C21—C26—C25 | 121.5 (3) |
C5—C6—H6 | 119.5 | C21—C26—H26 | 119.2 |
C7—C6—H6 | 119.5 | C25—C26—H26 | 119.2 |
N—C10—C11 | 122.8 (2) | C12—C13—C14 | 119.1 (2) |
N—C10—H10 | 118.6 | C12—C13—H13 | 120.5 |
C11—C10—H10 | 118.6 | C14—C13—H13 | 120.5 |
C6—C7—C2 | 119.3 (2) | C5—C4—C3 | 120.1 (2) |
C6—C7—N | 122.7 (2) | C5—C4—H4 | 119.9 |
C2—C7—N | 118.0 (2) | C3—C4—H4 | 119.9 |
C15—C14—C13 | 120.8 (2) | C24—C25—C26 | 119.7 (3) |
C15—C14—H14 | 119.6 | C24—C25—H25 | 120.1 |
C13—C14—H14 | 119.6 | C26—C25—H25 | 120.1 |
C4—C3—C2 | 121.3 (2) | S1—C1—H1A | 109.5 |
C4—C3—H3 | 119.3 | S1—C1—H1B | 109.5 |
C2—C3—H3 | 119.3 | H1A—C1—H1B | 109.5 |
C12—C11—C16 | 118.3 (2) | S1—C1—H1C | 109.5 |
C12—C11—C10 | 120.27 (19) | H1A—C1—H1C | 109.5 |
C16—C11—C10 | 121.4 (2) | H1B—C1—H1C | 109.5 |
C20—S2—C16—C15 | −13.5 (2) | S2—C16—C11—C12 | 176.09 (17) |
C20—S2—C16—C11 | 168.75 (19) | C15—C16—C11—C10 | 175.7 (2) |
C1—S1—C2—C3 | −13.2 (2) | S2—C16—C11—C10 | −6.5 (3) |
C1—S1—C2—C7 | 167.53 (18) | N—C10—C11—C12 | −10.2 (3) |
C11—C16—C15—C14 | 1.5 (4) | N—C10—C11—C16 | 172.4 (2) |
S2—C16—C15—C14 | −176.2 (2) | C26—C21—C20—S2 | 94.9 (3) |
C7—N—C10—C11 | 175.94 (19) | C22—C21—C20—S2 | −85.3 (2) |
C5—C6—C7—C2 | −3.7 (3) | C16—S2—C20—C21 | −176.76 (18) |
C5—C6—C7—N | 178.5 (2) | C7—C6—C5—C4 | −0.4 (4) |
C3—C2—C7—C6 | 5.1 (3) | C26—C21—C22—C23 | 0.0 (4) |
S1—C2—C7—C6 | −175.54 (16) | C20—C21—C22—C23 | −179.8 (2) |
C3—C2—C7—N | −176.94 (18) | C25—C24—C23—C22 | 0.3 (4) |
S1—C2—C7—N | 2.4 (3) | C21—C22—C23—C24 | 0.1 (4) |
C10—N—C7—C6 | −41.5 (3) | C22—C21—C26—C25 | −0.5 (4) |
C10—N—C7—C2 | 140.7 (2) | C20—C21—C26—C25 | 179.3 (2) |
C16—C15—C14—C13 | −0.4 (4) | C11—C12—C13—C14 | 0.2 (4) |
C7—C2—C3—C4 | −2.6 (3) | C15—C14—C13—C12 | −0.4 (4) |
S1—C2—C3—C4 | 178.10 (19) | C6—C5—C4—C3 | 3.0 (4) |
C13—C12—C11—C16 | 0.9 (3) | C2—C3—C4—C5 | −1.5 (4) |
C13—C12—C11—C10 | −176.6 (2) | C23—C24—C25—C26 | −0.9 (4) |
C15—C16—C11—C12 | −1.7 (3) | C21—C26—C25—C24 | 1.0 (4) |