Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229620009626/ep3007sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620009626/ep30077sup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620009626/ep30078sup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620009626/ep30076sup2.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229620009626/ep30078sup7.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229620009626/ep30076sup5.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229620009626/ep30077sup6.cml | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2053229620009626/ep3007sup8.pdf |
CCDC references: 2004452; 2004453; 2004454
For all structures, data collection: APEX2 (Bruker, 2012); cell refinement: APEX2 (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXT2018 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b) and ShelXle (Hübschle et al., 2011); molecular graphics: ORTEP-3 for Windows (Johnson, 1965, 1976; Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2020) and Mercury (Macrae et al., 2020).
C15H11IN2O2S | F(000) = 800 |
Mr = 410.22 | Dx = 1.875 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.9586 (6) Å | Cell parameters from 7151 reflections |
b = 10.2679 (6) Å | θ = 2.5–28.0° |
c = 12.9392 (8) Å | µ = 2.35 mm−1 |
β = 93.624 (3)° | T = 296 K |
V = 1453.03 (15) Å3 | Platelet, yellow |
Z = 4 | 0.49 × 0.36 × 0.06 mm |
Bruker APEXII CCD diffractometer | 3628 independent reflections |
Radiation source: sealed tube | 2871 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
Detector resolution: 8.3333 pixels mm-1 | θmax = 28.5°, θmin = 1.9° |
φ and ω scans | h = −14→14 |
Absorption correction: numerical (SADABS; Bruker, 2012) | k = −13→13 |
Tmin = 0.763, Tmax = 1.000 | l = −17→17 |
19964 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.150 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0905P)2 + 2.0774P] where P = (Fo2 + 2Fc2)/3 |
3628 reflections | (Δ/σ)max = 0.001 |
190 parameters | Δρmax = 1.86 e Å−3 |
0 restraints | Δρmin = −1.09 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Carbon-bound H atoms were placed in calculated positions and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2 Ueq(C). Two reflections with large differences between their observed and calculated intensities were omitted. This is due to obstruction by the beam stop. Single-crystal X-ray diffraction data were collected at 296 K on a Bruker APEXII CCD diffractometer with graphite-monochromated Mo Kα radiation using the APEX2 data collection software and SAINT (Bruker, 2012) for cell refinement and data reduction. The structures were solved by dual-space methods applying SHELXT-2018/2 (Sheldrick, 2015a) and refined by least-squares procedures using SHELXL-2018/3 (Sheldrick, 2015b). Data were corrected for absorption effects using the numerical method implemented in SADABS (Bruker, 2012). All non-hydrogen atoms were refined anisotropically and the carbon-bound hydrogen atoms were added in idealized geometrical positions in a riding model. The crystal structure diagrams were drawn with ORTEP-3 for windows (Johnson, 1965; 1976; Farrugia, 2012). |
x | y | z | Uiso*/Ueq | ||
I1 | 1.01660 (3) | 0.46280 (3) | 0.16942 (3) | 0.06583 (18) | |
S1 | 0.70749 (8) | 0.75401 (9) | 0.41931 (8) | 0.0379 (2) | |
O1 | 0.8074 (3) | 0.7664 (4) | 0.4940 (3) | 0.0613 (9) | |
O2 | 0.6731 (4) | 0.8659 (3) | 0.3584 (3) | 0.0624 (9) | |
N1 | 0.5073 (3) | 0.5693 (3) | 0.3420 (2) | 0.0324 (6) | |
N2 | 0.5882 (3) | 0.7021 (3) | 0.4798 (2) | 0.0335 (6) | |
C1 | 0.4936 (3) | 0.6383 (3) | 0.4240 (2) | 0.0290 (6) | |
C2 | 0.5695 (4) | 0.7534 (4) | 0.5854 (3) | 0.0407 (8) | |
H2A | 0.636382 | 0.810999 | 0.607258 | 0.049* | |
H2B | 0.568488 | 0.681763 | 0.634225 | 0.049* | |
C3 | 0.4510 (4) | 0.8261 (4) | 0.5847 (3) | 0.0448 (9) | |
H3A | 0.456633 | 0.905008 | 0.543989 | 0.054* | |
H3B | 0.434757 | 0.850892 | 0.654831 | 0.054* | |
C11 | 0.6227 (3) | 0.5507 (3) | 0.3062 (2) | 0.0293 (6) | |
C12 | 0.7255 (3) | 0.6235 (3) | 0.3372 (2) | 0.0302 (7) | |
C13 | 0.8396 (3) | 0.6004 (3) | 0.2992 (3) | 0.0354 (7) | |
H13 | 0.907117 | 0.650186 | 0.321468 | 0.042* | |
C14 | 0.8503 (4) | 0.5020 (4) | 0.2277 (3) | 0.0361 (7) | |
C15 | 0.7487 (4) | 0.4288 (4) | 0.1941 (3) | 0.0400 (8) | |
H15 | 0.756778 | 0.362938 | 0.145654 | 0.048* | |
C16 | 0.6363 (4) | 0.4529 (4) | 0.2319 (3) | 0.0372 (8) | |
H16 | 0.568830 | 0.403990 | 0.208068 | 0.045* | |
C21 | 0.3706 (3) | 0.6515 (3) | 0.4628 (3) | 0.0310 (7) | |
C22 | 0.3482 (3) | 0.7433 (4) | 0.5396 (3) | 0.0369 (8) | |
C23 | 0.2295 (4) | 0.7573 (5) | 0.5695 (3) | 0.0489 (10) | |
H23 | 0.213387 | 0.818906 | 0.619466 | 0.059* | |
C24 | 0.1357 (4) | 0.6830 (5) | 0.5274 (4) | 0.0562 (12) | |
H24 | 0.056878 | 0.694086 | 0.548763 | 0.067* | |
C25 | 0.1585 (4) | 0.5911 (5) | 0.4528 (4) | 0.0534 (11) | |
H25 | 0.094778 | 0.539973 | 0.424588 | 0.064* | |
C26 | 0.2745 (4) | 0.5745 (4) | 0.4199 (3) | 0.0413 (8) | |
H26 | 0.289054 | 0.512725 | 0.369543 | 0.050* |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.0549 (2) | 0.0607 (3) | 0.0861 (3) | −0.00008 (14) | 0.03780 (19) | −0.01542 (16) |
S1 | 0.0315 (4) | 0.0329 (4) | 0.0506 (5) | −0.0050 (3) | 0.0134 (4) | −0.0122 (4) |
O1 | 0.0339 (15) | 0.082 (2) | 0.068 (2) | −0.0142 (15) | 0.0099 (14) | −0.0392 (18) |
O2 | 0.074 (2) | 0.0292 (14) | 0.088 (2) | 0.0057 (14) | 0.0405 (19) | 0.0050 (15) |
N1 | 0.0285 (14) | 0.0386 (15) | 0.0301 (13) | −0.0017 (12) | 0.0031 (11) | −0.0050 (11) |
N2 | 0.0280 (14) | 0.0397 (16) | 0.0335 (14) | −0.0027 (12) | 0.0088 (11) | −0.0097 (12) |
C1 | 0.0267 (15) | 0.0305 (15) | 0.0300 (15) | 0.0007 (12) | 0.0024 (12) | 0.0012 (12) |
C2 | 0.0400 (19) | 0.047 (2) | 0.0350 (17) | −0.0013 (17) | 0.0056 (14) | −0.0137 (15) |
C3 | 0.047 (2) | 0.044 (2) | 0.045 (2) | 0.0035 (18) | 0.0142 (17) | −0.0107 (17) |
C11 | 0.0282 (16) | 0.0322 (16) | 0.0278 (14) | 0.0005 (12) | 0.0045 (12) | −0.0015 (12) |
C12 | 0.0314 (16) | 0.0281 (15) | 0.0316 (15) | 0.0006 (12) | 0.0071 (13) | −0.0036 (12) |
C13 | 0.0300 (16) | 0.0329 (17) | 0.0442 (18) | −0.0014 (14) | 0.0109 (14) | −0.0042 (14) |
C14 | 0.0364 (18) | 0.0358 (17) | 0.0374 (17) | 0.0019 (15) | 0.0137 (14) | −0.0024 (14) |
C15 | 0.047 (2) | 0.0387 (18) | 0.0351 (17) | −0.0001 (17) | 0.0121 (15) | −0.0073 (15) |
C16 | 0.0377 (19) | 0.0404 (19) | 0.0339 (17) | −0.0048 (15) | 0.0050 (14) | −0.0097 (14) |
C21 | 0.0259 (15) | 0.0332 (16) | 0.0345 (16) | 0.0051 (13) | 0.0058 (12) | 0.0061 (13) |
C22 | 0.0364 (18) | 0.0411 (19) | 0.0338 (16) | 0.0095 (15) | 0.0087 (14) | 0.0043 (14) |
C23 | 0.041 (2) | 0.061 (3) | 0.046 (2) | 0.015 (2) | 0.0143 (17) | 0.0056 (19) |
C24 | 0.031 (2) | 0.079 (3) | 0.060 (3) | 0.014 (2) | 0.0143 (18) | 0.020 (2) |
C25 | 0.0276 (18) | 0.066 (3) | 0.067 (3) | −0.0008 (19) | 0.0033 (18) | 0.012 (2) |
C26 | 0.0298 (17) | 0.045 (2) | 0.049 (2) | 0.0005 (16) | 0.0018 (15) | 0.0051 (17) |
I1—C14 | 2.055 (4) | C12—C13 | 1.393 (5) |
S1—O1 | 1.419 (3) | C13—C14 | 1.379 (5) |
S1—O2 | 1.430 (4) | C13—H13 | 0.9300 |
S1—N2 | 1.653 (3) | C14—C15 | 1.391 (6) |
S1—C12 | 1.729 (3) | C15—C16 | 1.376 (6) |
N1—C1 | 1.293 (4) | C15—H15 | 0.9300 |
N1—C11 | 1.388 (4) | C16—H16 | 0.9300 |
N2—C1 | 1.389 (4) | C21—C26 | 1.403 (5) |
N2—C2 | 1.491 (4) | C21—C22 | 1.403 (5) |
C1—C21 | 1.474 (5) | C22—C23 | 1.388 (6) |
C2—C3 | 1.498 (6) | C23—C24 | 1.365 (7) |
C2—H2A | 0.9700 | C23—H23 | 0.9300 |
C2—H2B | 0.9700 | C24—C25 | 1.384 (8) |
C3—C22 | 1.500 (6) | C24—H24 | 0.9300 |
C3—H3A | 0.9700 | C25—C26 | 1.376 (6) |
C3—H3B | 0.9700 | C25—H25 | 0.9300 |
C11—C12 | 1.389 (5) | C26—H26 | 0.9300 |
C11—C16 | 1.405 (5) | ||
O1—S1—O2 | 117.9 (2) | C14—C13—C12 | 118.6 (3) |
O1—S1—N2 | 107.81 (19) | C14—C13—H13 | 120.7 |
O2—S1—N2 | 109.33 (19) | C12—C13—H13 | 120.7 |
O1—S1—C12 | 112.00 (19) | C13—C14—C15 | 120.3 (3) |
O2—S1—C12 | 108.68 (19) | C13—C14—I1 | 120.3 (3) |
N2—S1—C12 | 99.50 (16) | C15—C14—I1 | 119.4 (3) |
C1—N1—C11 | 120.3 (3) | C16—C15—C14 | 120.6 (3) |
C1—N2—C2 | 120.1 (3) | C16—C15—H15 | 119.7 |
C1—N2—S1 | 119.5 (2) | C14—C15—H15 | 119.7 |
C2—N2—S1 | 118.6 (2) | C15—C16—C11 | 120.5 (3) |
N1—C1—N2 | 124.3 (3) | C15—C16—H16 | 119.8 |
N1—C1—C21 | 119.0 (3) | C11—C16—H16 | 119.8 |
N2—C1—C21 | 116.7 (3) | C26—C21—C22 | 119.9 (3) |
N2—C2—C3 | 109.9 (3) | C26—C21—C1 | 119.6 (3) |
N2—C2—H2A | 109.7 | C22—C21—C1 | 120.5 (3) |
C3—C2—H2A | 109.7 | C23—C22—C21 | 118.4 (4) |
N2—C2—H2B | 109.7 | C23—C22—C3 | 121.8 (4) |
C3—C2—H2B | 109.7 | C21—C22—C3 | 119.7 (3) |
H2A—C2—H2B | 108.2 | C24—C23—C22 | 121.8 (4) |
C2—C3—C22 | 110.5 (3) | C24—C23—H23 | 119.1 |
C2—C3—H3A | 109.6 | C22—C23—H23 | 119.1 |
C22—C3—H3A | 109.6 | C23—C24—C25 | 119.6 (4) |
C2—C3—H3B | 109.6 | C23—C24—H24 | 120.2 |
C22—C3—H3B | 109.6 | C25—C24—H24 | 120.2 |
H3A—C3—H3B | 108.1 | C26—C25—C24 | 120.8 (4) |
N1—C11—C12 | 124.6 (3) | C26—C25—H25 | 119.6 |
N1—C11—C16 | 117.7 (3) | C24—C25—H25 | 119.6 |
C12—C11—C16 | 117.6 (3) | C25—C26—C21 | 119.5 (4) |
C11—C12—C13 | 122.4 (3) | C25—C26—H26 | 120.2 |
C11—C12—S1 | 118.2 (3) | C21—C26—H26 | 120.2 |
C13—C12—S1 | 119.3 (3) | ||
O1—S1—N2—C1 | −157.1 (3) | C11—C12—C13—C14 | 0.4 (5) |
O2—S1—N2—C1 | 73.5 (3) | S1—C12—C13—C14 | −175.2 (3) |
C12—S1—N2—C1 | −40.2 (3) | C12—C13—C14—C15 | 0.5 (6) |
O1—S1—N2—C2 | 38.2 (3) | C12—C13—C14—I1 | −179.7 (3) |
O2—S1—N2—C2 | −91.1 (3) | C13—C14—C15—C16 | −0.3 (6) |
C12—S1—N2—C2 | 155.1 (3) | I1—C14—C15—C16 | 179.9 (3) |
C11—N1—C1—N2 | 2.5 (5) | C14—C15—C16—C11 | −0.9 (6) |
C11—N1—C1—C21 | −177.3 (3) | N1—C11—C16—C15 | −179.4 (3) |
C2—N2—C1—N1 | −166.0 (4) | C12—C11—C16—C15 | 1.8 (5) |
S1—N2—C1—N1 | 29.6 (5) | N1—C1—C21—C26 | 9.3 (5) |
C2—N2—C1—C21 | 13.8 (5) | N2—C1—C21—C26 | −170.5 (3) |
S1—N2—C1—C21 | −150.6 (3) | N1—C1—C21—C22 | −168.6 (3) |
C1—N2—C2—C3 | −46.8 (5) | N2—C1—C21—C22 | 11.6 (5) |
S1—N2—C2—C3 | 117.8 (3) | C26—C21—C22—C23 | −1.5 (5) |
N2—C2—C3—C22 | 52.9 (4) | C1—C21—C22—C23 | 176.4 (3) |
C1—N1—C11—C12 | −15.1 (5) | C26—C21—C22—C3 | −179.5 (3) |
C1—N1—C11—C16 | 166.1 (3) | C1—C21—C22—C3 | −1.7 (5) |
N1—C11—C12—C13 | 179.7 (3) | C2—C3—C22—C23 | 150.6 (4) |
C16—C11—C12—C13 | −1.5 (5) | C2—C3—C22—C21 | −31.4 (5) |
N1—C11—C12—S1 | −4.7 (5) | C21—C22—C23—C24 | 1.1 (6) |
C16—C11—C12—S1 | 174.1 (3) | C3—C22—C23—C24 | 179.1 (4) |
O1—S1—C12—C11 | 142.0 (3) | C22—C23—C24—C25 | −0.1 (7) |
O2—S1—C12—C11 | −85.9 (3) | C23—C24—C25—C26 | −0.6 (7) |
N2—S1—C12—C11 | 28.3 (3) | C24—C25—C26—C21 | 0.2 (7) |
O1—S1—C12—C13 | −42.3 (4) | C22—C21—C26—C25 | 0.8 (6) |
O2—S1—C12—C13 | 89.8 (3) | C1—C21—C26—C25 | −177.0 (4) |
N2—S1—C12—C13 | −156.0 (3) |
C15H14N2O4S | F(000) = 664 |
Mr = 318.34 | Dx = 1.446 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.048 (2) Å | Cell parameters from 9277 reflections |
b = 13.802 (3) Å | θ = 2.4–28.3° |
c = 10.543 (2) Å | µ = 0.24 mm−1 |
β = 90.487 (10)° | T = 296 K |
V = 1462.2 (5) Å3 | Block, colourless |
Z = 4 | 0.71 × 0.44 × 0.37 mm |
Bruker APEXII CCD diffractometer | 3655 independent reflections |
Radiation source: sealed tube | 3186 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
Detector resolution: 8.3333 pixels mm-1 | θmax = 28.4°, θmin = 2.4° |
φ and ω scans | h = −13→13 |
Absorption correction: numerical (SADABS; Bruker, 2012) | k = −18→18 |
Tmin = 0.953, Tmax = 1.000 | l = −14→14 |
88246 measured reflections |
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)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.099 | w = 1/[σ2(Fo2) + (0.0497P)2 + 0.3875P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
3655 reflections | Δρmax = 0.26 e Å−3 |
200 parameters | Δρmin = −0.32 e Å−3 |
0 restraints | Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: dual | Extinction coefficient: 0.0196 (17) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Carbon-bound H atoms were placed in calculated positions and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2 Ueq(C). Single-crystal X-ray diffraction data were collected at 296 K on a Bruker APEXII CCD diffractometer with graphite-monochromated Mo Kα radiation using the APEX2 data collection software and SAINT (Bruker, 2012) for cell refinement and data reduction. The structures were solved by dual-space methods applying SHELXT-2018/2 (Sheldrick, 2015a) and refined by least-squares procedures using SHELXL-2018/3 (Sheldrick, 2015b). Data were corrected for absorption effects using the numerical method implemented in SADABS (Bruker, 2012). All non-hydrogen atoms were refined anisotropically and the carbon-bound hydrogen atoms were added in idealized geometrical positions in a riding model. The crystal structure diagrams were drawn with ORTEP-3 for windows (Johnson, 1965; 1976; Farrugia, 2012). |
x | y | z | Uiso*/Ueq | ||
S1 | 0.22434 (3) | 0.26068 (2) | 0.60528 (3) | 0.04245 (12) | |
O1 | 0.50587 (11) | 0.20404 (9) | 0.77057 (11) | 0.0604 (3) | |
O2 | 0.38599 (13) | 0.11032 (8) | 0.88638 (13) | 0.0684 (3) | |
O3 | 0.08662 (11) | 0.26975 (10) | 0.57400 (11) | 0.0639 (3) | |
O4 | 0.28485 (13) | 0.16783 (7) | 0.60442 (10) | 0.0601 (3) | |
N1 | 0.40900 (12) | 0.18751 (8) | 0.83468 (11) | 0.0447 (3) | |
N2 | 0.30384 (11) | 0.32965 (8) | 0.50775 (10) | 0.0387 (2) | |
C11 | 0.23944 (12) | 0.30865 (9) | 0.76181 (12) | 0.0378 (3) | |
C12 | 0.31513 (12) | 0.26713 (9) | 0.85821 (12) | 0.0382 (3) | |
C13 | 0.30676 (14) | 0.29842 (12) | 0.98299 (13) | 0.0512 (3) | |
H13 | 0.354690 | 0.267156 | 1.046770 | 0.061* | |
C14 | 0.22664 (16) | 0.37633 (13) | 1.01123 (16) | 0.0595 (4) | |
H14 | 0.220668 | 0.398329 | 1.094359 | 0.071* | |
C15 | 0.15540 (17) | 0.42156 (12) | 0.91610 (17) | 0.0609 (4) | |
H15 | 0.104449 | 0.475901 | 0.934740 | 0.073* | |
C16 | 0.15893 (14) | 0.38686 (11) | 0.79286 (15) | 0.0507 (3) | |
H16 | 0.106949 | 0.416177 | 0.730354 | 0.061* | |
C21 | 0.24900 (13) | 0.42650 (10) | 0.48524 (13) | 0.0429 (3) | |
H21A | 0.267296 | 0.467345 | 0.558201 | 0.052* | |
H21B | 0.153214 | 0.422111 | 0.474512 | 0.052* | |
C22 | 0.30903 (13) | 0.47152 (9) | 0.36841 (11) | 0.0383 (3) | |
C23 | 0.24522 (16) | 0.55062 (11) | 0.31337 (14) | 0.0503 (3) | |
H23 | 0.166312 | 0.573547 | 0.347718 | 0.060* | |
C24 | 0.29830 (19) | 0.59550 (12) | 0.20775 (15) | 0.0596 (4) | |
H24 | 0.255336 | 0.648539 | 0.171586 | 0.071* | |
C25 | 0.41473 (18) | 0.56144 (12) | 0.15648 (14) | 0.0576 (4) | |
H25 | 0.450102 | 0.591103 | 0.085093 | 0.069* | |
C26 | 0.47847 (15) | 0.48399 (11) | 0.21043 (13) | 0.0508 (3) | |
H26 | 0.557377 | 0.461662 | 0.175409 | 0.061* | |
C27 | 0.42689 (13) | 0.43775 (9) | 0.31754 (12) | 0.0405 (3) | |
C28 | 0.49646 (14) | 0.35160 (11) | 0.37493 (14) | 0.0506 (3) | |
H28A | 0.591487 | 0.363952 | 0.377085 | 0.061* | |
H28B | 0.481158 | 0.295572 | 0.321219 | 0.061* | |
C29 | 0.45009 (13) | 0.32842 (10) | 0.50848 (13) | 0.0450 (3) | |
H29A | 0.482405 | 0.265121 | 0.534232 | 0.054* | |
H29B | 0.484281 | 0.376232 | 0.567793 | 0.054* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0496 (2) | 0.04094 (18) | 0.03662 (18) | −0.01290 (13) | −0.00905 (13) | 0.00428 (12) |
O1 | 0.0539 (6) | 0.0632 (7) | 0.0643 (7) | 0.0073 (5) | 0.0114 (5) | 0.0065 (5) |
O2 | 0.0834 (8) | 0.0445 (6) | 0.0772 (8) | −0.0024 (5) | 0.0016 (6) | 0.0179 (5) |
O3 | 0.0494 (6) | 0.0888 (8) | 0.0534 (6) | −0.0281 (6) | −0.0163 (5) | 0.0193 (6) |
O4 | 0.0991 (9) | 0.0331 (5) | 0.0480 (6) | −0.0088 (5) | −0.0127 (5) | −0.0023 (4) |
N1 | 0.0480 (6) | 0.0434 (6) | 0.0427 (6) | −0.0013 (5) | −0.0067 (5) | 0.0030 (5) |
N2 | 0.0410 (5) | 0.0378 (5) | 0.0373 (5) | 0.0013 (4) | 0.0002 (4) | 0.0046 (4) |
C11 | 0.0372 (6) | 0.0376 (6) | 0.0385 (6) | −0.0076 (5) | 0.0000 (5) | 0.0033 (5) |
C12 | 0.0347 (6) | 0.0399 (6) | 0.0401 (6) | −0.0081 (5) | −0.0030 (5) | −0.0001 (5) |
C13 | 0.0447 (7) | 0.0685 (9) | 0.0401 (7) | −0.0084 (6) | −0.0060 (5) | −0.0058 (6) |
C14 | 0.0539 (8) | 0.0724 (10) | 0.0523 (8) | −0.0098 (7) | 0.0060 (7) | −0.0202 (8) |
C15 | 0.0570 (9) | 0.0538 (9) | 0.0722 (11) | 0.0028 (7) | 0.0166 (8) | −0.0105 (8) |
C16 | 0.0465 (7) | 0.0501 (8) | 0.0558 (8) | 0.0045 (6) | 0.0063 (6) | 0.0078 (6) |
C21 | 0.0434 (6) | 0.0421 (7) | 0.0433 (7) | 0.0072 (5) | 0.0078 (5) | 0.0080 (5) |
C22 | 0.0425 (6) | 0.0371 (6) | 0.0355 (6) | −0.0017 (5) | 0.0018 (5) | 0.0015 (5) |
C23 | 0.0571 (8) | 0.0464 (7) | 0.0474 (7) | 0.0071 (6) | 0.0025 (6) | 0.0077 (6) |
C24 | 0.0815 (11) | 0.0471 (8) | 0.0500 (8) | −0.0018 (7) | −0.0031 (7) | 0.0138 (6) |
C25 | 0.0770 (10) | 0.0560 (9) | 0.0400 (7) | −0.0201 (8) | 0.0061 (7) | 0.0071 (6) |
C26 | 0.0529 (8) | 0.0571 (8) | 0.0425 (7) | −0.0127 (6) | 0.0103 (6) | −0.0050 (6) |
C27 | 0.0435 (6) | 0.0408 (6) | 0.0371 (6) | −0.0045 (5) | 0.0038 (5) | −0.0036 (5) |
C28 | 0.0464 (7) | 0.0524 (8) | 0.0530 (8) | 0.0102 (6) | 0.0112 (6) | 0.0002 (6) |
C29 | 0.0412 (6) | 0.0474 (7) | 0.0464 (7) | 0.0065 (5) | −0.0024 (5) | 0.0024 (6) |
S1—O4 | 1.4185 (12) | C21—C22 | 1.5099 (17) |
S1—O3 | 1.4254 (12) | C21—H21A | 0.9700 |
S1—N2 | 1.6172 (11) | C21—H21B | 0.9700 |
S1—C11 | 1.7835 (13) | C22—C27 | 1.3849 (18) |
O1—N1 | 1.2114 (16) | C22—C23 | 1.3905 (18) |
O2—N1 | 1.2197 (16) | C23—C24 | 1.385 (2) |
N1—C12 | 1.4707 (18) | C23—H23 | 0.9300 |
N2—C21 | 1.4645 (16) | C24—C25 | 1.376 (3) |
N2—C29 | 1.4696 (17) | C24—H24 | 0.9300 |
C11—C12 | 1.3880 (18) | C25—C26 | 1.368 (2) |
C11—C16 | 1.3898 (19) | C25—H25 | 0.9300 |
C12—C13 | 1.3878 (19) | C26—C27 | 1.4005 (18) |
C13—C14 | 1.377 (2) | C26—H26 | 0.9300 |
C13—H13 | 0.9300 | C27—C28 | 1.5039 (19) |
C14—C15 | 1.377 (3) | C28—C29 | 1.521 (2) |
C14—H14 | 0.9300 | C28—H28A | 0.9700 |
C15—C16 | 1.386 (2) | C28—H28B | 0.9700 |
C15—H15 | 0.9300 | C29—H29A | 0.9700 |
C16—H16 | 0.9300 | C29—H29B | 0.9700 |
O4—S1—O3 | 119.55 (8) | N2—C21—H21B | 109.5 |
O4—S1—N2 | 108.28 (7) | C22—C21—H21B | 109.5 |
O3—S1—N2 | 106.56 (6) | H21A—C21—H21B | 108.1 |
O4—S1—C11 | 107.95 (6) | C27—C22—C23 | 119.69 (12) |
O3—S1—C11 | 104.85 (7) | C27—C22—C21 | 121.76 (11) |
N2—S1—C11 | 109.35 (6) | C23—C22—C21 | 118.53 (12) |
O1—N1—O2 | 124.76 (13) | C24—C23—C22 | 120.49 (14) |
O1—N1—C12 | 118.22 (11) | C24—C23—H23 | 119.8 |
O2—N1—C12 | 116.94 (12) | C22—C23—H23 | 119.8 |
C21—N2—C29 | 112.72 (10) | C25—C24—C23 | 119.85 (15) |
C21—N2—S1 | 116.94 (8) | C25—C24—H24 | 120.1 |
C29—N2—S1 | 119.29 (9) | C23—C24—H24 | 120.1 |
C12—C11—C16 | 117.68 (12) | C26—C25—C24 | 120.03 (13) |
C12—C11—S1 | 124.49 (10) | C26—C25—H25 | 120.0 |
C16—C11—S1 | 117.46 (10) | C24—C25—H25 | 120.0 |
C13—C12—C11 | 121.90 (13) | C25—C26—C27 | 121.09 (14) |
C13—C12—N1 | 115.88 (12) | C25—C26—H26 | 119.5 |
C11—C12—N1 | 122.22 (11) | C27—C26—H26 | 119.5 |
C14—C13—C12 | 119.21 (14) | C22—C27—C26 | 118.85 (13) |
C14—C13—H13 | 120.4 | C22—C27—C28 | 120.42 (11) |
C12—C13—H13 | 120.4 | C26—C27—C28 | 120.72 (12) |
C15—C14—C13 | 119.85 (14) | C27—C28—C29 | 113.19 (11) |
C15—C14—H14 | 120.1 | C27—C28—H28A | 108.9 |
C13—C14—H14 | 120.1 | C29—C28—H28A | 108.9 |
C14—C15—C16 | 120.61 (15) | C27—C28—H28B | 108.9 |
C14—C15—H15 | 119.7 | C29—C28—H28B | 108.9 |
C16—C15—H15 | 119.7 | H28A—C28—H28B | 107.8 |
C15—C16—C11 | 120.59 (14) | N2—C29—C28 | 107.87 (11) |
C15—C16—H16 | 119.7 | N2—C29—H29A | 110.1 |
C11—C16—H16 | 119.7 | C28—C29—H29A | 110.1 |
N2—C21—C22 | 110.82 (10) | N2—C29—H29B | 110.1 |
N2—C21—H21A | 109.5 | C28—C29—H29B | 110.1 |
C22—C21—H21A | 109.5 | H29A—C29—H29B | 108.4 |
O4—S1—N2—C21 | 174.25 (10) | C14—C15—C16—C11 | −3.1 (2) |
O3—S1—N2—C21 | 44.45 (12) | C12—C11—C16—C15 | 0.1 (2) |
C11—S1—N2—C21 | −68.37 (11) | S1—C11—C16—C15 | 173.41 (12) |
O4—S1—N2—C29 | −44.33 (11) | C29—N2—C21—C22 | 51.67 (15) |
O3—S1—N2—C29 | −174.13 (11) | S1—N2—C21—C22 | −164.46 (9) |
C11—S1—N2—C29 | 73.05 (11) | N2—C21—C22—C27 | −18.59 (17) |
O4—S1—C11—C12 | 8.80 (13) | N2—C21—C22—C23 | 163.18 (12) |
O3—S1—C11—C12 | 137.28 (11) | C27—C22—C23—C24 | 0.3 (2) |
N2—S1—C11—C12 | −108.79 (11) | C21—C22—C23—C24 | 178.59 (14) |
O4—S1—C11—C16 | −164.02 (11) | C22—C23—C24—C25 | 0.3 (2) |
O3—S1—C11—C16 | −35.55 (12) | C23—C24—C25—C26 | −0.6 (2) |
N2—S1—C11—C16 | 78.38 (11) | C24—C25—C26—C27 | 0.3 (2) |
C16—C11—C12—C13 | 3.29 (19) | C23—C22—C27—C26 | −0.57 (19) |
S1—C11—C12—C13 | −169.52 (10) | C21—C22—C27—C26 | −178.78 (12) |
C16—C11—C12—N1 | −176.67 (11) | C23—C22—C27—C28 | −179.31 (13) |
S1—C11—C12—N1 | 10.51 (17) | C21—C22—C27—C28 | 2.48 (19) |
O1—N1—C12—C13 | −113.75 (14) | C25—C26—C27—C22 | 0.2 (2) |
O2—N1—C12—C13 | 63.11 (16) | C25—C26—C27—C28 | 178.98 (14) |
O1—N1—C12—C11 | 66.22 (16) | C22—C27—C28—C29 | −17.28 (19) |
O2—N1—C12—C11 | −116.92 (14) | C26—C27—C28—C29 | 164.01 (13) |
C11—C12—C13—C14 | −3.6 (2) | C21—N2—C29—C28 | −67.02 (14) |
N1—C12—C13—C14 | 176.35 (13) | S1—N2—C29—C28 | 150.04 (10) |
C12—C13—C14—C15 | 0.5 (2) | C27—C28—C29—N2 | 47.28 (16) |
C13—C14—C15—C16 | 2.8 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13···O3i | 0.93 | 2.40 | 3.1093 (19) | 133 |
C21—H21A···O2ii | 0.97 | 2.57 | 3.1843 (18) | 121 |
C21—H21B···O3 | 0.97 | 2.45 | 2.8713 (17) | 106 |
C29—H29A···O4 | 0.97 | 2.51 | 2.9532 (18) | 108 |
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+1/2, y+1/2, −z+3/2. |
C15H16N2O2S | F(000) = 608 |
Mr = 288.36 | Dx = 1.358 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.3376 (5) Å | Cell parameters from 9944 reflections |
b = 12.6151 (5) Å | θ = 2.5–28.1° |
c = 10.8850 (5) Å | µ = 0.23 mm−1 |
β = 96.590 (2)° | T = 296 K |
V = 1410.13 (11) Å3 | Platelet, colourless |
Z = 4 | 0.70 × 0.63 × 0.25 mm |
Bruker APEXII CCD diffractometer | 3524 independent reflections |
Radiation source: sealed tube | 2860 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
Detector resolution: 8.3333 pixels mm-1 | θmax = 28.4°, θmin = 2.5° |
φ and ω scans | h = −13→13 |
Absorption correction: numerical (SADABS; Bruker, 2012) | k = −16→16 |
Tmin = 0.938, Tmax = 1.000 | l = −14→14 |
24938 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.035 | Hydrogen site location: mixed |
wR(F2) = 0.103 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0514P)2 + 0.3199P] where P = (Fo2 + 2Fc2)/3 |
3524 reflections | (Δ/σ)max < 0.001 |
189 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.36 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Carbon-bound H atoms were placed in calculated positions and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2 Ueq(C). The nitrogen-bound H atoms were located on a difference map and refined freely. Single-crystal X-ray diffraction data were collected at 296 K on a Bruker APEXII CCD diffractometer with graphite-monochromated Mo Kα radiation using the APEX2 data collection software and SAINT (Bruker, 2012) for cell refinement and data reduction. The structures were solved by dual-space methods applying SHELXT-2018/2 (Sheldrick, 2015a) and refined by least-squares procedures using SHELXL-2018/3 (Sheldrick, 2015b). Data were corrected for absorption effects using the numerical method implemented in SADABS (Bruker, 2012). All non-hydrogen atoms were refined anisotropically and the carbon-bound hydrogen atoms were added in idealized geometrical positions in a riding model. The crystal structure diagrams were drawn with ORTEP-3 for windows (Johnson, 1965; 1976; Farrugia, 2012). |
x | y | z | Uiso*/Ueq | ||
S1 | 0.36887 (3) | 0.30805 (3) | 0.41884 (3) | 0.03528 (11) | |
O1 | 0.34861 (12) | 0.19583 (8) | 0.41677 (10) | 0.0495 (3) | |
O2 | 0.49141 (10) | 0.34827 (10) | 0.47555 (9) | 0.0479 (3) | |
N1 | 0.19007 (18) | 0.22126 (15) | 0.19078 (17) | 0.0631 (4) | |
N2 | 0.25856 (11) | 0.35848 (9) | 0.49702 (10) | 0.0349 (3) | |
C1 | 0.25700 (14) | 0.47423 (11) | 0.50735 (13) | 0.0380 (3) | |
H1A | 0.214333 | 0.504656 | 0.431445 | 0.046* | |
H1B | 0.345581 | 0.500824 | 0.519821 | 0.046* | |
C2 | 0.06877 (16) | 0.33107 (13) | 0.60393 (16) | 0.0501 (4) | |
H2A | −0.024753 | 0.320862 | 0.589619 | 0.060* | |
H2B | 0.103838 | 0.277716 | 0.662725 | 0.060* | |
C3 | 0.12588 (14) | 0.31450 (13) | 0.48327 (15) | 0.0447 (3) | |
H3A | 0.128283 | 0.239482 | 0.464112 | 0.054* | |
H3B | 0.072729 | 0.350037 | 0.416401 | 0.054* | |
C11 | 0.34692 (13) | 0.35721 (11) | 0.26712 (12) | 0.0356 (3) | |
C12 | 0.25866 (14) | 0.31072 (12) | 0.17451 (13) | 0.0417 (3) | |
C13 | 0.24247 (17) | 0.36177 (16) | 0.05937 (14) | 0.0549 (4) | |
H13 | 0.183682 | 0.334057 | −0.003531 | 0.066* | |
C14 | 0.31081 (19) | 0.45126 (17) | 0.03702 (16) | 0.0628 (5) | |
H14 | 0.297303 | 0.483392 | −0.040281 | 0.075* | |
C15 | 0.39995 (19) | 0.49467 (15) | 0.12815 (17) | 0.0588 (5) | |
H15 | 0.447519 | 0.554593 | 0.111808 | 0.071* | |
C16 | 0.41707 (15) | 0.44793 (13) | 0.24301 (15) | 0.0455 (3) | |
H16 | 0.475807 | 0.476966 | 0.305053 | 0.055* | |
C21 | 0.18557 (13) | 0.50654 (12) | 0.61447 (12) | 0.0370 (3) | |
C22 | 0.09610 (13) | 0.43882 (12) | 0.65963 (13) | 0.0400 (3) | |
C23 | 0.03411 (16) | 0.47287 (15) | 0.76068 (15) | 0.0529 (4) | |
H23 | −0.026015 | 0.428583 | 0.792175 | 0.063* | |
C24 | 0.06035 (16) | 0.57013 (17) | 0.81395 (15) | 0.0581 (5) | |
H24 | 0.018948 | 0.590748 | 0.881572 | 0.070* | |
C25 | 0.14736 (17) | 0.63706 (16) | 0.76791 (16) | 0.0584 (5) | |
H25 | 0.164088 | 0.703503 | 0.803229 | 0.070* | |
C26 | 0.21007 (16) | 0.60530 (14) | 0.66878 (15) | 0.0492 (4) | |
H26 | 0.269526 | 0.650614 | 0.637909 | 0.059* | |
H1C | 0.140 (2) | 0.1999 (17) | 0.134 (2) | 0.072 (7)* | |
H1D | 0.208 (2) | 0.1835 (16) | 0.255 (2) | 0.067 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.03212 (18) | 0.0394 (2) | 0.03337 (17) | 0.00473 (13) | −0.00013 (12) | 0.00224 (13) |
O1 | 0.0616 (7) | 0.0373 (6) | 0.0492 (6) | 0.0098 (5) | 0.0046 (5) | 0.0044 (4) |
O2 | 0.0306 (5) | 0.0674 (7) | 0.0438 (6) | 0.0037 (5) | −0.0041 (4) | 0.0023 (5) |
N1 | 0.0664 (10) | 0.0648 (10) | 0.0532 (9) | −0.0158 (8) | −0.0148 (8) | −0.0044 (8) |
N2 | 0.0312 (6) | 0.0366 (6) | 0.0373 (6) | −0.0041 (5) | 0.0055 (4) | −0.0011 (5) |
C1 | 0.0374 (7) | 0.0385 (7) | 0.0395 (7) | −0.0049 (6) | 0.0102 (5) | −0.0018 (5) |
C2 | 0.0397 (8) | 0.0495 (9) | 0.0634 (10) | −0.0062 (7) | 0.0153 (7) | 0.0086 (7) |
C3 | 0.0339 (7) | 0.0452 (8) | 0.0544 (9) | −0.0095 (6) | 0.0029 (6) | −0.0032 (6) |
C11 | 0.0336 (7) | 0.0415 (7) | 0.0318 (6) | 0.0079 (6) | 0.0043 (5) | 0.0011 (5) |
C12 | 0.0370 (7) | 0.0504 (8) | 0.0372 (7) | 0.0100 (6) | 0.0028 (6) | −0.0046 (6) |
C13 | 0.0491 (9) | 0.0798 (13) | 0.0343 (7) | 0.0148 (9) | −0.0021 (6) | −0.0016 (7) |
C14 | 0.0605 (11) | 0.0862 (14) | 0.0429 (9) | 0.0230 (10) | 0.0114 (8) | 0.0203 (9) |
C15 | 0.0608 (11) | 0.0597 (11) | 0.0587 (10) | 0.0051 (9) | 0.0197 (8) | 0.0181 (8) |
C16 | 0.0422 (8) | 0.0490 (8) | 0.0460 (8) | 0.0016 (7) | 0.0080 (6) | 0.0029 (6) |
C21 | 0.0307 (6) | 0.0451 (8) | 0.0350 (6) | 0.0006 (6) | 0.0035 (5) | −0.0014 (5) |
C22 | 0.0307 (7) | 0.0527 (9) | 0.0369 (7) | 0.0024 (6) | 0.0049 (5) | 0.0069 (6) |
C23 | 0.0391 (8) | 0.0785 (12) | 0.0427 (8) | 0.0048 (8) | 0.0115 (6) | 0.0114 (8) |
C24 | 0.0443 (9) | 0.0918 (14) | 0.0385 (8) | 0.0128 (9) | 0.0059 (6) | −0.0123 (8) |
C25 | 0.0457 (9) | 0.0737 (12) | 0.0548 (9) | 0.0033 (9) | 0.0019 (7) | −0.0257 (9) |
C26 | 0.0409 (8) | 0.0544 (9) | 0.0525 (9) | −0.0055 (7) | 0.0065 (7) | −0.0139 (7) |
S1—O1 | 1.4309 (11) | C11—C12 | 1.408 (2) |
S1—O2 | 1.4366 (11) | C12—C13 | 1.402 (2) |
S1—N2 | 1.6285 (12) | C13—C14 | 1.368 (3) |
S1—C11 | 1.7542 (13) | C13—H13 | 0.9300 |
N1—C12 | 1.355 (2) | C14—C15 | 1.387 (3) |
N1—H1C | 0.81 (2) | C14—H14 | 0.9300 |
N1—H1D | 0.84 (2) | C15—C16 | 1.375 (2) |
N2—C1 | 1.4648 (18) | C15—H15 | 0.9300 |
N2—C3 | 1.4712 (17) | C16—H16 | 0.9300 |
C1—C21 | 1.5062 (19) | C21—C22 | 1.390 (2) |
C1—H1A | 0.9700 | C21—C26 | 1.390 (2) |
C1—H1B | 0.9700 | C22—C23 | 1.402 (2) |
C2—C22 | 1.502 (2) | C23—C24 | 1.371 (3) |
C2—C3 | 1.515 (2) | C23—H23 | 0.9300 |
C2—H2A | 0.9700 | C24—C25 | 1.370 (3) |
C2—H2B | 0.9700 | C24—H24 | 0.9300 |
C3—H3A | 0.9700 | C25—C26 | 1.380 (2) |
C3—H3B | 0.9700 | C25—H25 | 0.9300 |
C11—C16 | 1.396 (2) | C26—H26 | 0.9300 |
O1—S1—O2 | 118.45 (7) | N1—C12—C13 | 119.26 (15) |
O1—S1—N2 | 106.54 (6) | N1—C12—C11 | 124.01 (14) |
O2—S1—N2 | 105.86 (6) | C13—C12—C11 | 116.73 (15) |
O1—S1—C11 | 109.40 (7) | C14—C13—C12 | 121.80 (16) |
O2—S1—C11 | 106.98 (7) | C14—C13—H13 | 119.1 |
N2—S1—C11 | 109.34 (6) | C12—C13—H13 | 119.1 |
C12—N1—H1C | 118.6 (16) | C13—C14—C15 | 120.86 (15) |
C12—N1—H1D | 120.6 (14) | C13—C14—H14 | 119.6 |
H1C—N1—H1D | 120 (2) | C15—C14—H14 | 119.6 |
C1—N2—C3 | 111.43 (11) | C16—C15—C14 | 119.11 (17) |
C1—N2—S1 | 116.37 (9) | C16—C15—H15 | 120.4 |
C3—N2—S1 | 120.00 (10) | C14—C15—H15 | 120.4 |
N2—C1—C21 | 109.87 (11) | C15—C16—C11 | 120.47 (16) |
N2—C1—H1A | 109.7 | C15—C16—H16 | 119.8 |
C21—C1—H1A | 109.7 | C11—C16—H16 | 119.8 |
N2—C1—H1B | 109.7 | C22—C21—C26 | 119.79 (14) |
C21—C1—H1B | 109.7 | C22—C21—C1 | 120.85 (13) |
H1A—C1—H1B | 108.2 | C26—C21—C1 | 119.35 (13) |
C22—C2—C3 | 113.64 (12) | C21—C22—C23 | 118.14 (15) |
C22—C2—H2A | 108.8 | C21—C22—C2 | 121.03 (13) |
C3—C2—H2A | 108.8 | C23—C22—C2 | 120.81 (14) |
C22—C2—H2B | 108.8 | C24—C23—C22 | 121.32 (16) |
C3—C2—H2B | 108.8 | C24—C23—H23 | 119.3 |
H2A—C2—H2B | 107.7 | C22—C23—H23 | 119.3 |
N2—C3—C2 | 108.14 (12) | C25—C24—C23 | 120.22 (15) |
N2—C3—H3A | 110.1 | C25—C24—H24 | 119.9 |
C2—C3—H3A | 110.1 | C23—C24—H24 | 119.9 |
N2—C3—H3B | 110.1 | C24—C25—C26 | 119.60 (17) |
C2—C3—H3B | 110.1 | C24—C25—H25 | 120.2 |
H3A—C3—H3B | 108.4 | C26—C25—H25 | 120.2 |
C16—C11—C12 | 121.00 (13) | C25—C26—C21 | 120.91 (16) |
C16—C11—S1 | 116.94 (11) | C25—C26—H26 | 119.5 |
C12—C11—S1 | 122.00 (11) | C21—C26—H26 | 119.5 |
O1—S1—N2—C1 | −177.66 (10) | C11—C12—C13—C14 | 1.2 (2) |
O2—S1—N2—C1 | 55.39 (11) | C12—C13—C14—C15 | 0.4 (3) |
C11—S1—N2—C1 | −59.54 (11) | C13—C14—C15—C16 | −1.4 (3) |
O1—S1—N2—C3 | −38.45 (12) | C14—C15—C16—C11 | 0.8 (3) |
O2—S1—N2—C3 | −165.39 (11) | C12—C11—C16—C15 | 0.9 (2) |
C11—S1—N2—C3 | 79.68 (12) | S1—C11—C16—C15 | −176.48 (13) |
C3—N2—C1—C21 | 56.94 (15) | N2—C1—C21—C22 | −22.43 (18) |
S1—N2—C1—C21 | −160.49 (9) | N2—C1—C21—C26 | 157.38 (13) |
C1—N2—C3—C2 | −68.32 (15) | C26—C21—C22—C23 | −0.7 (2) |
S1—N2—C3—C2 | 150.63 (11) | C1—C21—C22—C23 | 179.12 (13) |
C22—C2—C3—N2 | 42.95 (18) | C26—C21—C22—C2 | −179.23 (14) |
O1—S1—C11—C16 | −151.08 (11) | C1—C21—C22—C2 | 0.6 (2) |
O2—S1—C11—C16 | −21.61 (13) | C3—C2—C22—C21 | −11.2 (2) |
N2—S1—C11—C16 | 92.59 (12) | C3—C2—C22—C23 | 170.24 (14) |
O1—S1—C11—C12 | 31.61 (14) | C21—C22—C23—C24 | 0.0 (2) |
O2—S1—C11—C12 | 161.08 (11) | C2—C22—C23—C24 | 178.59 (15) |
N2—S1—C11—C12 | −84.72 (12) | C22—C23—C24—C25 | 0.8 (3) |
C16—C11—C12—N1 | 178.24 (16) | C23—C24—C25—C26 | −1.0 (3) |
S1—C11—C12—N1 | −4.6 (2) | C24—C25—C26—C21 | 0.4 (3) |
C16—C11—C12—C13 | −1.8 (2) | C22—C21—C26—C25 | 0.5 (2) |
S1—C11—C12—C13 | 175.35 (11) | C1—C21—C26—C25 | −179.33 (15) |
N1—C12—C13—C14 | −178.85 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1C···O2i | 0.81 (2) | 2.26 (2) | 3.0612 (19) | 176 (2) |
N1—H1D···O1 | 0.84 (2) | 2.16 (2) | 2.813 (2) | 134.0 (18) |
C1—H1B···O2 | 0.97 | 2.52 | 2.9512 (18) | 107 |
C1—H1B···O2ii | 0.97 | 2.54 | 3.4207 (18) | 151 |
C3—H3A···O1 | 0.97 | 2.45 | 2.9067 (19) | 108 |
C16—H16···O2 | 0.93 | 2.46 | 2.8516 (19) | 106 |
C23—H23···O1iii | 0.93 | 2.53 | 3.441 (2) | 168 |
Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) −x+1, −y+1, −z+1; (iii) x−1/2, −y+1/2, z+1/2. |
Compound | D—H···A | D—H | H···A | D···A | D—H···A< | Slippage* |
6 | C13—H13···O3i | 0.93 | 2.40 | 3.1093 (19) | 133 | |
C21—H21A···O2ii | 0.97 | 2.57 | 3.1843 (18) | 121 | ||
C21—H21B···O3 | 0.97 | 2.45 | 2.8713 (17) | 106 | ||
C29—H29A···O4 | 0.97 | 2.51 | 2.9532 (18) | 108 | ||
C29—H29B···Cg1iii | 0.97 | 2.78 | 3.7264 (17) | 166 | ||
C14—H14···Cg1iv | 0.93 | 2.79 | 3.544 (2) | 139 | ||
7 | N1—H1C···O2v | 0.81 (2) | 2.26 (2) | 3.0612 (19) | 176 (2) | |
N1—H1D···O1 | 0.84 (2) | 2.16 (2) | 2.813 (2) | 134.0 (18) | ||
C1—H1B···O2 | 0.97 | 2.52 | 2.9512 (18) | 107 | ||
C1—H1B···O2vi | 0.97 | 2.54 | 3.4207 (18) | 151 | ||
C3—H3A···O1 | 0.97 | 2.45 | 2.9067 (19) | 108 | ||
C16—H16···O2 | 0.93 | 2.46 | 2.8516 (19) | 106 | ||
C23—H23···O1vii | 0.93 | 2.53 | 3.441 (2) | 168 | ||
C3—H3B···Cg2viii | 0.97 | 2.72 | 3.6575 (17) | 162 | ||
8 | C2—H2A···O1 | 0.97 | 2.49 | 2.934 (5) | 107 | |
C3—H3B···N1ix | 0.97 | 2.63 | 3.515 (5) | 152 | ||
C2—H2A···Cg3ix | 0.97 | 2.82 | 3.662 (4) | 146 | ||
C15—H15···Cg4x | 0.93 | 2.72 | 3.639 (4) | 172 | ||
Cg3···Cg4xi | 3.666 (2) | 0.877 | ||||
Cg4···Cg3xi | 3.666 (2) | 0.927 |
Symmetry codes: (i) x+1/2, -y+1/2, z+1/2;
(ii) –x+1/2, y+1/2, –z+3/2;
(iii) –x+1, –y+1, –z+1;
(iv) x, y, z+1;
(v) x-1/2, -y+1/2, z-1/2;
(vi) -x+1, -y+1, -z+1;
(vii) x-1/2, -y+1/2, z+1/2;
(viii) –x, –y+1, –z+1;
(ix) x, –y+3/2, z+1/2;
(x) –x+1, y–1/2, –z+1/2;
(xi) –x+1, –y+1, –z+1. Cg1 is the centroid of the C22–C27 ring, Cg2 of the C21–C26 ring, Cg3 of the C11–C16 ring and Cg4 of the C21–C26 ring. Note: (*) PLATON (Spek, 2020) calculated different values for the two interactions. |
Compound | Global energy | Attractive VdW | Repulsive VdW | ACE | GSC score | AI area |
(kcal mol-1) | (kcal mol-1) | (kcal mol-1) | (kcal mol-1) | |||
6 | -53.90 | -17.36 | +6.09 | -327 | 3906 | 423 |
7 | -54.69 | -17.96 | +4.22 | -341 | 3822 | 418 |
8 | -52.30 | -15.53 | +4.17 | -281 | 3598 | 390 |