Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229620009328/fm3064sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620009328/fm3064Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620009328/fm3064IIsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620009328/fm3064IIIsup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620009328/fm3064IVsup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620009328/fm3064Vsup6.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620009328/fm3064VIsup7.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229620009328/fm3064VIIsup8.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229620009328/fm3064Isup9.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229620009328/fm3064IIsup10.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229620009328/fm3064IIIsup11.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229620009328/fm3064IVsup12.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229620009328/fm3064Vsup13.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229620009328/fm3064VIsup14.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229620009328/fm3064VIIsup15.cml | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2053229620009328/fm3064sup16.pdf |
CCDC references: 1481284; 1972774; 1481282; 1875930; 1875954; 1576559; 1972792
Data collection: FRAMBO (Bruker, 2009) for (I); CrysAlis PRO (Agilent, 2013) for (II), (III), (IV), (V), (VI), (VII). Cell refinement: FRAMBO (Bruker, 2009) for (I); CrysAlis PRO (Agilent, 2013) for (II), (III), (IV), (V), (VI), (VII). Data reduction: SHELXTL (Bruker, 2000) for (I); CrysAlis PRO (Agilent, 2013) for (II), (III), (IV), (V), (VI), (VII). Program(s) used to solve structure: olex2.solve (Bourhis et al., 2015) for (I), (VI), (VII); SUPERFLIP (Palatinus & Chapuis, 2007; Palatinus & van der Lee, 2008; Palatinus et al., 2012) for (II); SHELXS97 (Sheldrick, 2008) for (III), (IV), (V). For all structures, program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009), PLATON (Spek, 2020) and publCIF (Westrip, 2010).
C19H22N4O3S | Z = 2 |
Mr = 386.46 | F(000) = 408 |
Triclinic, P1 | Dx = 1.339 Mg m−3 |
a = 9.1209 (17) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.6732 (19) Å | Cell parameters from 2041 reflections |
c = 11.958 (2) Å | θ = 2.8–26.4° |
α = 104.763 (17)° | µ = 0.20 mm−1 |
β = 100.147 (15)° | T = 295 K |
γ = 103.858 (17)° | Prism, colourless |
V = 958.4 (3) Å3 | 0.4 × 0.35 × 0.25 mm |
Xcalibur 3 diffractometer | 2037 reflections with I > 2σ(I) |
phi and ω scans | Rint = 0.032 |
Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012) | θmax = 26.4°, θmin = 2.8° |
Tmin = 0.957, Tmax = 1.038 | h = −11→11 |
8686 measured reflections | k = −8→12 |
3842 independent reflections | l = −14→14 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.042 | H-atom parameters constrained |
wR(F2) = 0.095 | w = 1/[σ2(Fo2) + (0.038P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
3842 reflections | Δρmax = 0.35 e Å−3 |
246 parameters | Δρmin = −0.21 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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.11874 (7) | 0.35535 (6) | 0.31730 (5) | 0.04464 (19) | |
N3 | 0.2652 (2) | 0.59934 (17) | 0.26016 (14) | 0.0411 (4) | |
N4 | 0.1350 (2) | 0.64544 (16) | 0.22494 (14) | 0.0419 (4) | |
H4 | 0.101492 | 0.601422 | 0.134228 | 0.050* | |
O1 | 0.41191 (19) | 0.28613 (16) | 0.38001 (13) | 0.0595 (4) | |
C4 | −0.0408 (2) | 0.4147 (2) | 0.24743 (17) | 0.0381 (5) | |
H4A | −0.120437 | 0.385988 | 0.292629 | 0.046* | |
O2 | 0.6474 (2) | 0.40289 (18) | 0.36494 (16) | 0.0718 (5) | |
O3 | −0.0416 (2) | 0.36910 (16) | 0.04306 (13) | 0.0814 (6) | |
C6 | −0.1853 (3) | 0.1605 (2) | 0.08551 (18) | 0.0428 (5) | |
C3 | 0.0039 (3) | 0.5855 (2) | 0.27300 (18) | 0.0401 (5) | |
C1 | 0.2740 (3) | 0.4807 (2) | 0.29763 (16) | 0.0380 (5) | |
N2 | 0.4072 (2) | 0.68261 (19) | 0.25891 (16) | 0.0532 (5) | |
N1 | 0.5076 (2) | 0.6166 (2) | 0.29365 (17) | 0.0567 (5) | |
C5 | −0.0883 (3) | 0.3188 (2) | 0.11743 (18) | 0.0477 (6) | |
C16 | 0.0406 (3) | 0.6683 (2) | 0.40761 (18) | 0.0491 (6) | |
H16A | 0.003856 | 0.599086 | 0.449901 | 0.059* | |
H16B | 0.152176 | 0.714255 | 0.440283 | 0.059* | |
C2 | 0.4315 (3) | 0.4941 (2) | 0.31995 (18) | 0.0442 (6) | |
C13 | 0.5124 (3) | 0.3939 (2) | 0.35769 (19) | 0.0500 (6) | |
C19 | −0.1307 (3) | 0.6353 (2) | 0.2181 (2) | 0.0543 (6) | |
H19A | −0.128684 | 0.635789 | 0.137327 | 0.065* | |
H19B | −0.230308 | 0.569130 | 0.215974 | 0.065* | |
C9 | −0.3552 (3) | −0.1424 (2) | 0.0197 (2) | 0.0538 (6) | |
C11 | −0.2743 (3) | 0.1071 (2) | 0.1555 (2) | 0.0548 (6) | |
H11 | −0.277717 | 0.172522 | 0.226352 | 0.066* | |
C10 | −0.3586 (3) | −0.0417 (2) | 0.1221 (2) | 0.0601 (7) | |
H10 | −0.419297 | −0.074697 | 0.170471 | 0.072* | |
C7 | −0.1838 (3) | 0.0602 (3) | −0.0197 (2) | 0.0669 (8) | |
H7 | −0.127390 | 0.093846 | −0.070222 | 0.080* | |
C12 | −0.4474 (3) | −0.3062 (2) | −0.0144 (2) | 0.0762 (8) | |
H12A | −0.487335 | −0.324810 | 0.051173 | 0.114* | |
H12B | −0.380675 | −0.367180 | −0.033165 | 0.114* | |
H12C | −0.532739 | −0.330427 | −0.082948 | 0.114* | |
C14 | 0.4675 (3) | 0.1682 (3) | 0.4071 (3) | 0.0756 (8) | |
H14A | 0.521152 | 0.130667 | 0.348304 | 0.091* | |
H14B | 0.540784 | 0.206663 | 0.485161 | 0.091* | |
C8 | −0.2656 (3) | −0.0892 (3) | −0.0500 (2) | 0.0719 (8) | |
H8 | −0.259940 | −0.155680 | −0.119493 | 0.086* | |
C18 | −0.1049 (3) | 0.7919 (3) | 0.2988 (2) | 0.0713 (8) | |
H18A | −0.030864 | 0.865374 | 0.278094 | 0.086* | |
H18B | −0.202171 | 0.817029 | 0.293947 | 0.086* | |
C17 | −0.0417 (4) | 0.7849 (3) | 0.4199 (2) | 0.0914 (10) | |
H17A | −0.126059 | 0.759870 | 0.457539 | 0.110* | |
H17B | 0.030244 | 0.881408 | 0.469485 | 0.110* | |
C15 | 0.3388 (4) | 0.0503 (3) | 0.4058 (4) | 0.1248 (14) | |
H15A | 0.375739 | −0.027836 | 0.425164 | 0.187* | |
H15B | 0.268026 | 0.010891 | 0.327765 | 0.187* | |
H15C | 0.285693 | 0.088182 | 0.463689 | 0.187* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0409 (4) | 0.0449 (3) | 0.0521 (4) | 0.0107 (3) | 0.0138 (3) | 0.0225 (3) |
N3 | 0.0359 (13) | 0.0399 (10) | 0.0468 (10) | 0.0069 (9) | 0.0145 (9) | 0.0139 (8) |
N4 | 0.0378 (13) | 0.0435 (10) | 0.0467 (10) | 0.0106 (9) | 0.0122 (9) | 0.0185 (8) |
O1 | 0.0495 (12) | 0.0582 (10) | 0.0791 (11) | 0.0218 (9) | 0.0134 (9) | 0.0320 (9) |
C4 | 0.0323 (14) | 0.0435 (12) | 0.0406 (12) | 0.0081 (10) | 0.0110 (10) | 0.0184 (10) |
O2 | 0.0445 (13) | 0.0784 (11) | 0.1012 (14) | 0.0281 (10) | 0.0247 (11) | 0.0291 (10) |
O3 | 0.1188 (18) | 0.0608 (10) | 0.0455 (10) | −0.0142 (10) | 0.0224 (10) | 0.0213 (8) |
C6 | 0.0414 (16) | 0.0433 (12) | 0.0387 (13) | 0.0065 (11) | 0.0059 (11) | 0.0130 (11) |
C3 | 0.0344 (15) | 0.0424 (12) | 0.0466 (13) | 0.0116 (11) | 0.0123 (11) | 0.0177 (10) |
C1 | 0.0415 (16) | 0.0358 (11) | 0.0367 (12) | 0.0112 (11) | 0.0136 (11) | 0.0092 (9) |
N2 | 0.0410 (14) | 0.0520 (11) | 0.0698 (13) | 0.0087 (11) | 0.0228 (11) | 0.0236 (10) |
N1 | 0.0403 (14) | 0.0578 (12) | 0.0733 (14) | 0.0112 (11) | 0.0228 (11) | 0.0201 (10) |
C5 | 0.0498 (17) | 0.0493 (13) | 0.0412 (13) | 0.0073 (12) | 0.0093 (12) | 0.0180 (11) |
C16 | 0.0515 (17) | 0.0456 (12) | 0.0495 (14) | 0.0131 (12) | 0.0165 (12) | 0.0123 (11) |
C2 | 0.0392 (17) | 0.0445 (13) | 0.0498 (13) | 0.0129 (12) | 0.0169 (12) | 0.0119 (11) |
C13 | 0.0444 (19) | 0.0548 (15) | 0.0495 (14) | 0.0187 (14) | 0.0158 (13) | 0.0075 (12) |
C19 | 0.0432 (17) | 0.0587 (14) | 0.0693 (16) | 0.0191 (13) | 0.0150 (13) | 0.0299 (13) |
C9 | 0.0592 (19) | 0.0438 (13) | 0.0482 (15) | 0.0064 (13) | 0.0045 (13) | 0.0119 (12) |
C11 | 0.0616 (19) | 0.0418 (13) | 0.0580 (15) | 0.0080 (12) | 0.0248 (13) | 0.0105 (11) |
C10 | 0.066 (2) | 0.0473 (14) | 0.0674 (17) | 0.0078 (13) | 0.0298 (14) | 0.0186 (13) |
C7 | 0.078 (2) | 0.0596 (16) | 0.0490 (15) | −0.0036 (15) | 0.0232 (14) | 0.0098 (13) |
C12 | 0.097 (3) | 0.0433 (14) | 0.0704 (18) | 0.0018 (15) | 0.0118 (16) | 0.0122 (12) |
C14 | 0.071 (2) | 0.0674 (17) | 0.097 (2) | 0.0291 (17) | 0.0133 (17) | 0.0370 (15) |
C8 | 0.088 (2) | 0.0551 (15) | 0.0532 (16) | 0.0034 (15) | 0.0233 (15) | −0.0024 (12) |
C18 | 0.0583 (19) | 0.0560 (15) | 0.114 (2) | 0.0263 (14) | 0.0247 (17) | 0.0405 (16) |
C17 | 0.138 (3) | 0.0692 (17) | 0.083 (2) | 0.060 (2) | 0.035 (2) | 0.0176 (15) |
C15 | 0.088 (3) | 0.073 (2) | 0.203 (4) | 0.017 (2) | −0.007 (3) | 0.060 (2) |
S1—C4 | 1.834 (2) | C19—H19A | 0.9700 |
S1—C1 | 1.724 (2) | C19—H19B | 0.9700 |
N3—N4 | 1.400 (2) | C19—C18 | 1.512 (3) |
N3—C1 | 1.348 (2) | C9—C10 | 1.367 (3) |
N3—N2 | 1.356 (2) | C9—C12 | 1.515 (3) |
N4—H4 | 1.0182 | C9—C8 | 1.373 (3) |
N4—C3 | 1.475 (2) | C11—H11 | 0.9300 |
O1—C13 | 1.329 (3) | C11—C10 | 1.376 (3) |
O1—C14 | 1.439 (2) | C10—H10 | 0.9300 |
C4—H4A | 1.0074 | C7—H7 | 0.9300 |
C4—C3 | 1.538 (3) | C7—C8 | 1.377 (3) |
C4—C5 | 1.517 (3) | C12—H12A | 0.9600 |
O2—C13 | 1.200 (3) | C12—H12B | 0.9600 |
O3—C5 | 1.210 (2) | C12—H12C | 0.9600 |
C6—C5 | 1.486 (3) | C14—H14A | 0.9700 |
C6—C11 | 1.372 (3) | C14—H14B | 0.9700 |
C6—C7 | 1.384 (3) | C14—C15 | 1.423 (4) |
C3—C16 | 1.539 (3) | C8—H8 | 0.9300 |
C3—C19 | 1.527 (3) | C18—H18A | 0.9700 |
C1—C2 | 1.382 (3) | C18—H18B | 0.9700 |
N2—N1 | 1.304 (2) | C18—C17 | 1.487 (3) |
N1—C2 | 1.363 (2) | C17—H17A | 0.9700 |
C16—H16A | 0.9700 | C17—H17B | 0.9700 |
C16—H16B | 0.9700 | C15—H15A | 0.9600 |
C16—C17 | 1.489 (3) | C15—H15B | 0.9600 |
C2—C13 | 1.461 (3) | C15—H15C | 0.9600 |
C1—S1—C4 | 99.09 (9) | C18—C19—H19A | 110.8 |
C1—N3—N4 | 129.70 (17) | C18—C19—H19B | 110.8 |
C1—N3—N2 | 111.99 (17) | C10—C9—C12 | 120.7 (2) |
N2—N3—N4 | 118.31 (15) | C10—C9—C8 | 117.5 (2) |
N3—N4—H4 | 105.0 | C8—C9—C12 | 121.8 (2) |
N3—N4—C3 | 112.38 (14) | C6—C11—H11 | 119.6 |
C3—N4—H4 | 108.3 | C6—C11—C10 | 120.9 (2) |
C13—O1—C14 | 117.3 (2) | C10—C11—H11 | 119.6 |
S1—C4—H4A | 100.7 | C9—C10—C11 | 121.6 (2) |
C3—C4—S1 | 112.18 (14) | C9—C10—H10 | 119.2 |
C3—C4—H4A | 108.1 | C11—C10—H10 | 119.2 |
C5—C4—S1 | 104.56 (13) | C6—C7—H7 | 119.9 |
C5—C4—H4A | 113.0 | C8—C7—C6 | 120.3 (2) |
C5—C4—C3 | 117.07 (15) | C8—C7—H7 | 119.9 |
C11—C6—C5 | 123.79 (19) | C9—C12—H12A | 109.5 |
C11—C6—C7 | 118.0 (2) | C9—C12—H12B | 109.5 |
C7—C6—C5 | 118.2 (2) | C9—C12—H12C | 109.5 |
N4—C3—C4 | 113.75 (15) | H12A—C12—H12B | 109.5 |
N4—C3—C16 | 109.63 (18) | H12A—C12—H12C | 109.5 |
N4—C3—C19 | 105.38 (15) | H12B—C12—H12C | 109.5 |
C4—C3—C16 | 111.48 (15) | O1—C14—H14A | 109.8 |
C19—C3—C4 | 112.14 (18) | O1—C14—H14B | 109.8 |
C19—C3—C16 | 103.83 (17) | H14A—C14—H14B | 108.3 |
N3—C1—S1 | 124.99 (16) | C15—C14—O1 | 109.3 (2) |
N3—C1—C2 | 103.18 (17) | C15—C14—H14A | 109.8 |
C2—C1—S1 | 131.74 (16) | C15—C14—H14B | 109.8 |
N1—N2—N3 | 106.66 (15) | C9—C8—C7 | 121.7 (2) |
N2—N1—C2 | 109.1 (2) | C9—C8—H8 | 119.2 |
O3—C5—C4 | 120.18 (19) | C7—C8—H8 | 119.2 |
O3—C5—C6 | 121.28 (19) | C19—C18—H18A | 111.1 |
C6—C5—C4 | 118.46 (17) | C19—C18—H18B | 111.1 |
C3—C16—H16A | 110.4 | H18A—C18—H18B | 109.0 |
C3—C16—H16B | 110.4 | C17—C18—C19 | 103.51 (18) |
H16A—C16—H16B | 108.6 | C17—C18—H18A | 111.1 |
C17—C16—C3 | 106.58 (18) | C17—C18—H18B | 111.1 |
C17—C16—H16A | 110.4 | C16—C17—H17A | 110.0 |
C17—C16—H16B | 110.4 | C16—C17—H17B | 110.0 |
C1—C2—C13 | 128.8 (2) | C18—C17—C16 | 108.5 (2) |
N1—C2—C1 | 109.02 (19) | C18—C17—H17A | 110.0 |
N1—C2—C13 | 122.0 (2) | C18—C17—H17B | 110.0 |
O1—C13—C2 | 109.6 (2) | H17A—C17—H17B | 108.4 |
O2—C13—O1 | 124.2 (2) | C14—C15—H15A | 109.5 |
O2—C13—C2 | 126.2 (2) | C14—C15—H15B | 109.5 |
C3—C19—H19A | 110.8 | C14—C15—H15C | 109.5 |
C3—C19—H19B | 110.8 | H15A—C15—H15B | 109.5 |
H19A—C19—H19B | 108.8 | H15A—C15—H15C | 109.5 |
C18—C19—C3 | 104.97 (19) | H15B—C15—H15C | 109.5 |
S1—C4—C3—N4 | 62.33 (19) | C1—N3—N2—N1 | 1.0 (2) |
S1—C4—C3—C16 | −62.3 (2) | C1—C2—C13—O1 | −5.8 (3) |
S1—C4—C3—C19 | −178.20 (14) | C1—C2—C13—O2 | 172.4 (2) |
S1—C4—C5—O3 | −99.3 (2) | N2—N3—N4—C3 | −157.68 (16) |
S1—C4—C5—C6 | 77.3 (2) | N2—N3—C1—S1 | 176.81 (14) |
S1—C1—C2—N1 | −177.44 (15) | N2—N3—C1—C2 | −0.1 (2) |
S1—C1—C2—C13 | 6.5 (3) | N2—N1—C2—C1 | 1.5 (2) |
N3—N4—C3—C4 | −52.2 (2) | N2—N1—C2—C13 | 177.90 (18) |
N3—N4—C3—C16 | 73.37 (18) | N1—C2—C13—O1 | 178.64 (18) |
N3—N4—C3—C19 | −175.44 (15) | N1—C2—C13—O2 | −3.2 (3) |
N3—C1—C2—N1 | −0.8 (2) | C5—C4—C3—N4 | −58.6 (2) |
N3—C1—C2—C13 | −176.89 (19) | C5—C4—C3—C16 | 176.86 (19) |
N3—N2—N1—C2 | −1.5 (2) | C5—C4—C3—C19 | 60.9 (2) |
N4—N3—C1—S1 | −2.8 (3) | C5—C6—C11—C10 | −178.3 (2) |
N4—N3—C1—C2 | −179.70 (17) | C5—C6—C7—C8 | 176.7 (2) |
N4—N3—N2—N1 | −179.33 (16) | C16—C3—C19—C18 | 30.5 (2) |
N4—C3—C16—C17 | 98.7 (2) | C13—O1—C14—C15 | −169.0 (2) |
N4—C3—C19—C18 | −84.7 (2) | C19—C3—C16—C17 | −13.5 (2) |
C4—S1—C1—N3 | 10.11 (18) | C19—C18—C17—C16 | 27.8 (3) |
C4—S1—C1—C2 | −173.91 (19) | C11—C6—C5—C4 | 20.9 (3) |
C4—C3—C16—C17 | −134.4 (2) | C11—C6—C5—O3 | −162.5 (2) |
C4—C3—C19—C18 | 151.00 (18) | C11—C6—C7—C8 | −2.2 (4) |
C6—C11—C10—C9 | 1.0 (4) | C10—C9—C8—C7 | −1.1 (4) |
C6—C7—C8—C9 | 2.6 (4) | C7—C6—C5—C4 | −157.9 (2) |
C3—C4—C5—O3 | 25.5 (3) | C7—C6—C5—O3 | 18.8 (3) |
C3—C4—C5—C6 | −157.87 (19) | C7—C6—C11—C10 | 0.4 (4) |
C3—C16—C17—C18 | −8.8 (3) | C12—C9—C10—C11 | 179.2 (2) |
C3—C19—C18—C17 | −36.0 (3) | C12—C9—C8—C7 | 179.0 (3) |
C1—S1—C4—C3 | −37.08 (15) | C14—O1—C13—O2 | −4.1 (3) |
C1—S1—C4—C5 | 90.78 (14) | C14—O1—C13—C2 | 174.04 (18) |
C1—N3—N4—C3 | 21.9 (3) | C8—C9—C10—C11 | −0.7 (4) |
C19H22N4O4S | Z = 2 |
Mr = 402.46 | F(000) = 424 |
Triclinic, P1 | Dx = 1.349 Mg m−3 |
a = 9.1304 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.9986 (6) Å | Cell parameters from 3031 reflections |
c = 11.8551 (6) Å | θ = 2.7–29.5° |
α = 107.458 (5)° | µ = 0.20 mm−1 |
β = 99.719 (4)° | T = 295 K |
γ = 99.414 (5)° | Block, colourless |
V = 990.84 (10) Å3 | 0.3 × 0.25 × 0.2 mm |
Agilent Xcalibur Eos diffractometer | 4047 reflections with I > 2σ(I) |
Detector resolution: 15.9555 pixels mm-1 | Rint = 0.020 |
ω scans | θmax = 30.7°, θmin = 2.6° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013), | h = −12→12 |
Tmin = 0.934, Tmax = 1.000 | k = −12→14 |
9553 measured reflections | l = −16→16 |
5400 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.046 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.126 | w = 1/[σ2(Fo2) + (0.0544P)2 + 0.1655P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
5400 reflections | Δρmax = 0.32 e Å−3 |
272 parameters | Δρmin = −0.21 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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1 | 0.63535 (4) | 0.86556 (4) | 0.82226 (4) | 0.03722 (12) | |
N2 | 0.90546 (17) | 1.16932 (17) | 0.76171 (15) | 0.0515 (4) | |
C1 | 0.78297 (17) | 0.98041 (16) | 0.80070 (13) | 0.0347 (3) | |
O1 | 0.92725 (13) | 0.78557 (14) | 0.87498 (12) | 0.0508 (3) | |
N4 | 0.63771 (15) | 1.14353 (15) | 0.73287 (14) | 0.0382 (3) | |
O2 | 1.15593 (14) | 0.89089 (16) | 0.85833 (15) | 0.0655 (4) | |
N1 | 1.00736 (17) | 1.10155 (17) | 0.79347 (16) | 0.0534 (4) | |
C12 | 0.0156 (3) | 0.1971 (2) | 0.5076 (2) | 0.0743 (7) | |
H12A | −0.036149 | 0.099927 | 0.458967 | 0.112* | |
H12B | −0.058204 | 0.252542 | 0.529254 | 0.112* | |
H12C | 0.081284 | 0.197405 | 0.579980 | 0.112* | |
C13 | 1.02212 (19) | 0.8865 (2) | 0.85262 (16) | 0.0458 (4) | |
N3 | 0.76841 (14) | 1.09486 (14) | 0.76596 (12) | 0.0381 (3) | |
O4 | 0.10375 (19) | 0.25848 (15) | 0.44031 (14) | 0.0732 (4) | |
O3 | 0.4853 (2) | 0.88148 (15) | 0.54493 (12) | 0.0732 (5) | |
C16 | 0.3732 (2) | 1.13968 (19) | 0.72729 (17) | 0.0476 (4) | |
H16A | 0.374347 | 1.137104 | 0.645002 | 0.057* | |
H16B | 0.277945 | 1.079346 | 0.726216 | 0.057* | |
C4 | 0.47563 (17) | 0.92418 (16) | 0.75138 (13) | 0.0330 (3) | |
C2 | 0.93840 (18) | 0.98674 (18) | 0.81912 (15) | 0.0418 (4) | |
C3 | 0.51001 (17) | 1.08856 (17) | 0.78081 (14) | 0.0347 (3) | |
C9 | 0.1828 (2) | 0.39803 (19) | 0.49218 (17) | 0.0503 (4) | |
C8 | 0.1839 (2) | 0.4856 (2) | 0.60699 (18) | 0.0539 (5) | |
H8 | 0.129162 | 0.450442 | 0.655490 | 0.065* | |
C7 | 0.2675 (2) | 0.62695 (19) | 0.64941 (17) | 0.0487 (4) | |
H7 | 0.269886 | 0.685551 | 0.727534 | 0.058* | |
C6 | 0.34717 (18) | 0.68262 (17) | 0.57834 (14) | 0.0378 (3) | |
C18A | 0.5057 (5) | 1.3133 (5) | 0.9303 (5) | 0.0613 (11) | 0.65 |
H18A | 0.597960 | 1.384310 | 0.941642 | 0.074* | 0.65 |
H18B | 0.460490 | 1.345109 | 0.999246 | 0.074* | 0.65 |
C10 | 0.2649 (3) | 0.4508 (2) | 0.42086 (18) | 0.0631 (6) | |
H10 | 0.265687 | 0.390760 | 0.344087 | 0.076* | |
C5 | 0.43644 (19) | 0.83273 (18) | 0.61724 (14) | 0.0410 (4) | |
C19 | 0.5410 (2) | 1.16907 (18) | 0.91834 (15) | 0.0437 (4) | |
H19A | 0.476060 | 1.117195 | 0.955590 | 0.052* | 0.65 |
H19B | 0.646746 | 1.179966 | 0.957093 | 0.052* | 0.65 |
H19C | 0.517173 | 1.102225 | 0.960925 | 0.052* | 0.35 |
H19D | 0.647308 | 1.219471 | 0.950308 | 0.052* | 0.35 |
C11 | 0.3453 (2) | 0.5914 (2) | 0.46265 (16) | 0.0562 (5) | |
H11 | 0.398985 | 0.626304 | 0.413460 | 0.067* | |
C14 | 0.9854 (2) | 0.6676 (2) | 0.8971 (2) | 0.0666 (6) | |
H14A | 1.065507 | 0.703226 | 0.971078 | 0.080* | |
H14B | 1.027817 | 0.620407 | 0.830224 | 0.080* | |
C17 | 0.3920 (3) | 1.2929 (2) | 0.8106 (2) | 0.0684 (6) | |
H17A | 0.294461 | 1.309069 | 0.826719 | 0.082* | 0.65 |
H17B | 0.430991 | 1.360782 | 0.773085 | 0.082* | 0.65 |
H17C | 0.471304 | 1.359416 | 0.796846 | 0.082* | 0.35 |
H17D | 0.297243 | 1.324813 | 0.801311 | 0.082* | 0.35 |
C15 | 0.8590 (3) | 0.5655 (3) | 0.9090 (3) | 0.0860 (8) | |
H15A | 0.774900 | 0.540705 | 0.840237 | 0.129* | |
H15B | 0.827479 | 0.608743 | 0.982153 | 0.129* | |
H15C | 0.891961 | 0.480098 | 0.912494 | 0.129* | |
C18 | 0.4372 (11) | 1.2761 (10) | 0.9336 (8) | 0.063 (2) | 0.35 |
H18C | 0.347571 | 1.239491 | 0.958602 | 0.075* | 0.35 |
H18D | 0.491215 | 1.367970 | 0.994353 | 0.075* | 0.35 |
H4A | 0.3936 (19) | 0.8947 (18) | 0.7901 (15) | 0.038 (4)* | |
H4 | 0.614 (2) | 1.109 (2) | 0.6536 (18) | 0.051 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0358 (2) | 0.0378 (2) | 0.0424 (2) | 0.00641 (15) | 0.01321 (15) | 0.01855 (17) |
N2 | 0.0406 (8) | 0.0467 (9) | 0.0699 (10) | 0.0007 (6) | 0.0259 (7) | 0.0214 (8) |
C1 | 0.0344 (7) | 0.0335 (8) | 0.0342 (8) | 0.0054 (6) | 0.0129 (6) | 0.0071 (6) |
O1 | 0.0401 (6) | 0.0557 (8) | 0.0622 (8) | 0.0173 (6) | 0.0129 (5) | 0.0239 (6) |
N4 | 0.0391 (7) | 0.0360 (7) | 0.0434 (8) | 0.0066 (5) | 0.0150 (6) | 0.0173 (6) |
O2 | 0.0363 (7) | 0.0715 (10) | 0.0876 (10) | 0.0181 (6) | 0.0182 (6) | 0.0202 (8) |
N1 | 0.0391 (8) | 0.0506 (9) | 0.0701 (10) | 0.0045 (7) | 0.0245 (7) | 0.0164 (8) |
C12 | 0.0762 (15) | 0.0478 (12) | 0.0870 (17) | −0.0081 (10) | 0.0044 (12) | 0.0249 (12) |
C13 | 0.0366 (8) | 0.0500 (10) | 0.0442 (9) | 0.0102 (7) | 0.0124 (7) | 0.0047 (8) |
N3 | 0.0351 (7) | 0.0348 (7) | 0.0458 (7) | 0.0029 (5) | 0.0177 (5) | 0.0137 (6) |
O4 | 0.0939 (12) | 0.0378 (8) | 0.0668 (10) | −0.0104 (7) | 0.0165 (8) | 0.0019 (7) |
O3 | 0.1223 (13) | 0.0494 (9) | 0.0388 (7) | −0.0118 (8) | 0.0243 (8) | 0.0150 (6) |
C16 | 0.0406 (9) | 0.0494 (10) | 0.0588 (11) | 0.0138 (8) | 0.0137 (8) | 0.0238 (9) |
C4 | 0.0322 (7) | 0.0343 (8) | 0.0339 (7) | 0.0045 (6) | 0.0119 (6) | 0.0125 (6) |
C2 | 0.0343 (8) | 0.0434 (9) | 0.0443 (9) | 0.0066 (7) | 0.0159 (6) | 0.0073 (7) |
C3 | 0.0348 (7) | 0.0348 (8) | 0.0368 (8) | 0.0067 (6) | 0.0134 (6) | 0.0132 (6) |
C9 | 0.0562 (11) | 0.0345 (9) | 0.0490 (10) | 0.0026 (8) | 0.0051 (8) | 0.0060 (8) |
C8 | 0.0648 (12) | 0.0397 (10) | 0.0530 (11) | −0.0002 (8) | 0.0232 (9) | 0.0110 (8) |
C7 | 0.0603 (11) | 0.0381 (9) | 0.0422 (9) | 0.0025 (8) | 0.0200 (8) | 0.0061 (8) |
C6 | 0.0406 (8) | 0.0354 (8) | 0.0346 (8) | 0.0056 (6) | 0.0069 (6) | 0.0101 (7) |
C18A | 0.073 (3) | 0.038 (2) | 0.074 (3) | 0.0157 (19) | 0.032 (2) | 0.0104 (18) |
C10 | 0.0841 (15) | 0.0456 (11) | 0.0437 (10) | −0.0010 (10) | 0.0190 (10) | −0.0019 (9) |
C5 | 0.0493 (9) | 0.0382 (9) | 0.0342 (8) | 0.0052 (7) | 0.0099 (7) | 0.0126 (7) |
C19 | 0.0490 (9) | 0.0406 (9) | 0.0390 (8) | 0.0095 (7) | 0.0167 (7) | 0.0067 (7) |
C11 | 0.0729 (13) | 0.0474 (11) | 0.0388 (9) | −0.0020 (9) | 0.0191 (9) | 0.0061 (8) |
C14 | 0.0580 (12) | 0.0662 (14) | 0.0840 (16) | 0.0262 (11) | 0.0131 (11) | 0.0328 (12) |
C17 | 0.0754 (15) | 0.0510 (12) | 0.0891 (16) | 0.0297 (11) | 0.0233 (12) | 0.0281 (12) |
C15 | 0.0782 (17) | 0.0805 (18) | 0.111 (2) | 0.0172 (14) | 0.0099 (15) | 0.0563 (16) |
C18 | 0.095 (7) | 0.053 (5) | 0.048 (3) | 0.034 (5) | 0.027 (5) | 0.015 (4) |
S1—C1 | 1.7282 (16) | C8—C7 | 1.387 (2) |
S1—C4 | 1.8269 (15) | C7—H7 | 0.9300 |
N2—N1 | 1.307 (2) | C7—C6 | 1.380 (2) |
N2—N3 | 1.3644 (18) | C6—C5 | 1.479 (2) |
C1—N3 | 1.346 (2) | C6—C11 | 1.396 (2) |
C1—C2 | 1.387 (2) | C18A—H18A | 0.9700 |
O1—C13 | 1.338 (2) | C18A—H18B | 0.9700 |
O1—C14 | 1.444 (2) | C18A—C19 | 1.499 (5) |
N4—N3 | 1.4005 (18) | C18A—C17 | 1.547 (6) |
N4—C3 | 1.4785 (19) | C10—H10 | 0.9300 |
N4—H4 | 0.872 (19) | C10—C11 | 1.372 (3) |
O2—C13 | 1.205 (2) | C19—H19A | 0.9700 |
N1—C2 | 1.358 (2) | C19—H19B | 0.9700 |
C12—H12A | 0.9600 | C19—H19C | 0.9700 |
C12—H12B | 0.9600 | C19—H19D | 0.9700 |
C12—H12C | 0.9600 | C19—C18 | 1.533 (9) |
C12—O4 | 1.417 (3) | C11—H11 | 0.9300 |
C13—C2 | 1.461 (2) | C14—H14A | 0.9700 |
O4—C9 | 1.361 (2) | C14—H14B | 0.9700 |
O3—C5 | 1.217 (2) | C14—C15 | 1.467 (3) |
C16—H16A | 0.9700 | C17—H17A | 0.9700 |
C16—H16B | 0.9700 | C17—H17B | 0.9700 |
C16—C3 | 1.536 (2) | C17—H17C | 0.9700 |
C16—C17 | 1.517 (3) | C17—H17D | 0.9700 |
C4—C3 | 1.540 (2) | C17—C18 | 1.513 (9) |
C4—C5 | 1.524 (2) | C15—H15A | 0.9600 |
C4—H4A | 0.991 (17) | C15—H15B | 0.9600 |
C3—C19 | 1.539 (2) | C15—H15C | 0.9600 |
C9—C8 | 1.377 (3) | C18—H18C | 0.9700 |
C9—C10 | 1.381 (3) | C18—H18D | 0.9700 |
C8—H8 | 0.9300 | ||
C1—S1—C4 | 98.57 (7) | C19—C18A—H18A | 110.5 |
N1—N2—N3 | 106.29 (14) | C19—C18A—H18B | 110.5 |
N3—C1—S1 | 124.90 (11) | C19—C18A—C17 | 106.1 (3) |
N3—C1—C2 | 103.44 (14) | C17—C18A—H18A | 110.5 |
C2—C1—S1 | 131.57 (13) | C17—C18A—H18B | 110.5 |
C13—O1—C14 | 118.02 (14) | C9—C10—H10 | 119.8 |
N3—N4—C3 | 112.01 (12) | C11—C10—C9 | 120.36 (18) |
N3—N4—H4 | 104.0 (13) | C11—C10—H10 | 119.8 |
C3—N4—H4 | 110.0 (13) | O3—C5—C4 | 119.70 (15) |
N2—N1—C2 | 109.59 (14) | O3—C5—C6 | 121.02 (15) |
H12A—C12—H12B | 109.5 | C6—C5—C4 | 119.17 (14) |
H12A—C12—H12C | 109.5 | C3—C19—H19A | 110.6 |
H12B—C12—H12C | 109.5 | C3—C19—H19B | 110.6 |
O4—C12—H12A | 109.5 | C3—C19—H19C | 110.5 |
O4—C12—H12B | 109.5 | C3—C19—H19D | 110.5 |
O4—C12—H12C | 109.5 | C18A—C19—C3 | 105.6 (3) |
O1—C13—C2 | 109.81 (14) | C18A—C19—H19A | 110.6 |
O2—C13—O1 | 124.13 (18) | C18A—C19—H19B | 110.6 |
O2—C13—C2 | 126.06 (18) | H19A—C19—H19B | 108.8 |
N2—N3—N4 | 118.02 (13) | H19C—C19—H19D | 108.7 |
C1—N3—N2 | 111.86 (13) | C18—C19—C3 | 105.9 (4) |
C1—N3—N4 | 130.10 (13) | C18—C19—H19C | 110.5 |
C9—O4—C12 | 118.65 (17) | C18—C19—H19D | 110.5 |
H16A—C16—H16B | 108.8 | C6—C11—H11 | 119.7 |
C3—C16—H16A | 110.7 | C10—C11—C6 | 120.61 (18) |
C3—C16—H16B | 110.7 | C10—C11—H11 | 119.7 |
C17—C16—H16A | 110.7 | O1—C14—H14A | 110.0 |
C17—C16—H16B | 110.7 | O1—C14—H14B | 110.0 |
C17—C16—C3 | 105.13 (15) | O1—C14—C15 | 108.26 (17) |
S1—C4—H4A | 102.3 (9) | H14A—C14—H14B | 108.4 |
C3—C4—S1 | 112.08 (10) | C15—C14—H14A | 110.0 |
C3—C4—H4A | 109.8 (10) | C15—C14—H14B | 110.0 |
C5—C4—S1 | 105.53 (11) | C16—C17—C18A | 107.3 (2) |
C5—C4—C3 | 116.35 (13) | C16—C17—H17A | 110.3 |
C5—C4—H4A | 109.7 (10) | C16—C17—H17B | 110.3 |
C1—C2—C13 | 128.74 (16) | C16—C17—H17C | 111.7 |
N1—C2—C1 | 108.80 (15) | C16—C17—H17D | 111.7 |
N1—C2—C13 | 122.35 (15) | C18A—C17—H17A | 110.3 |
N4—C3—C16 | 105.40 (13) | C18A—C17—H17B | 110.3 |
N4—C3—C4 | 113.65 (12) | H17A—C17—H17B | 108.5 |
N4—C3—C19 | 109.47 (13) | H17C—C17—H17D | 109.4 |
C16—C3—C4 | 112.43 (13) | C18—C17—C16 | 100.6 (4) |
C16—C3—C19 | 103.66 (13) | C18—C17—H17C | 111.7 |
C19—C3—C4 | 111.59 (13) | C18—C17—H17D | 111.7 |
O4—C9—C8 | 124.53 (19) | C14—C15—H15A | 109.5 |
O4—C9—C10 | 115.39 (17) | C14—C15—H15B | 109.5 |
C8—C9—C10 | 120.07 (17) | C14—C15—H15C | 109.5 |
C9—C8—H8 | 120.4 | H15A—C15—H15B | 109.5 |
C9—C8—C7 | 119.23 (18) | H15A—C15—H15C | 109.5 |
C7—C8—H8 | 120.4 | H15B—C15—H15C | 109.5 |
C8—C7—H7 | 119.2 | C19—C18—H18C | 110.5 |
C6—C7—C8 | 121.51 (17) | C19—C18—H18D | 110.5 |
C6—C7—H7 | 119.2 | C17—C18—C19 | 106.1 (5) |
C7—C6—C5 | 124.25 (15) | C17—C18—H18C | 110.5 |
C7—C6—C11 | 118.18 (16) | C17—C18—H18D | 110.5 |
C11—C6—C5 | 117.57 (15) | H18C—C18—H18D | 108.7 |
H18A—C18A—H18B | 108.7 | ||
S1—C1—N3—N2 | 177.24 (11) | C4—S1—C1—N3 | 12.52 (15) |
S1—C1—N3—N4 | −4.2 (2) | C4—S1—C1—C2 | −171.49 (15) |
S1—C1—C2—N1 | −177.35 (13) | C4—C3—C19—C18A | −156.3 (2) |
S1—C1—C2—C13 | 6.4 (3) | C4—C3—C19—C18 | −129.1 (4) |
S1—C4—C3—N4 | 63.45 (15) | C2—C1—N3—N2 | 0.32 (18) |
S1—C4—C3—C16 | −176.92 (11) | C2—C1—N3—N4 | 178.90 (15) |
S1—C4—C3—C19 | −60.93 (14) | C3—N4—N3—N2 | −160.09 (14) |
S1—C4—C5—O3 | −98.04 (18) | C3—N4—N3—C1 | 21.4 (2) |
S1—C4—C5—C6 | 78.26 (16) | C3—C16—C17—C18A | −17.2 (3) |
N2—N1—C2—C1 | 0.9 (2) | C3—C16—C17—C18 | −43.1 (4) |
N2—N1—C2—C13 | 177.44 (15) | C3—C4—C5—O3 | 26.9 (2) |
C1—S1—C4—C3 | −39.23 (11) | C3—C4—C5—C6 | −156.77 (14) |
C1—S1—C4—C5 | 88.35 (11) | C3—C19—C18—C17 | −18.8 (6) |
O1—C13—C2—C1 | −5.3 (2) | C9—C8—C7—C6 | 1.3 (3) |
O1—C13—C2—N1 | 178.91 (16) | C9—C10—C11—C6 | 0.9 (3) |
N4—C3—C19—C18A | 77.0 (2) | C8—C9—C10—C11 | −1.4 (3) |
N4—C3—C19—C18 | 104.2 (4) | C8—C7—C6—C5 | 179.01 (17) |
O2—C13—C2—C1 | 173.82 (18) | C8—C7—C6—C11 | −1.8 (3) |
O2—C13—C2—N1 | −2.0 (3) | C7—C6—C5—O3 | −168.99 (18) |
N1—N2—N3—C1 | 0.2 (2) | C7—C6—C5—C4 | 14.8 (2) |
N1—N2—N3—N4 | −178.55 (14) | C7—C6—C11—C10 | 0.6 (3) |
C12—O4—C9—C8 | 0.1 (3) | C10—C9—C8—C7 | 0.3 (3) |
C12—O4—C9—C10 | −179.39 (19) | C5—C4—C3—N4 | −58.11 (18) |
C13—O1—C14—C15 | −175.32 (19) | C5—C4—C3—C16 | 61.52 (18) |
N3—N2—N1—C2 | −0.7 (2) | C5—C4—C3—C19 | 177.51 (13) |
N3—C1—C2—N1 | −0.73 (18) | C5—C6—C11—C10 | 179.93 (19) |
N3—C1—C2—C13 | −176.97 (16) | C19—C18A—C17—C16 | −4.4 (3) |
N3—N4—C3—C16 | −174.98 (13) | C11—C6—C5—O3 | 11.8 (3) |
N3—N4—C3—C4 | −51.42 (17) | C11—C6—C5—C4 | −164.48 (16) |
N3—N4—C3—C19 | 74.09 (16) | C14—O1—C13—O2 | −5.5 (3) |
O4—C9—C8—C7 | −179.16 (19) | C14—O1—C13—C2 | 173.60 (16) |
O4—C9—C10—C11 | 178.1 (2) | C17—C16—C3—N4 | −83.17 (17) |
C16—C3—C19—C18A | −35.0 (2) | C17—C16—C3—C4 | 152.51 (15) |
C16—C3—C19—C18 | −7.9 (4) | C17—C16—C3—C19 | 31.84 (18) |
C16—C17—C18—C19 | 37.8 (6) | C17—C18A—C19—C3 | 24.4 (3) |
C19H22N4O3S | F(000) = 408 |
Mr = 386.46 | Dx = 1.356 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.8289 (6) Å | Cell parameters from 2546 reflections |
b = 18.0940 (18) Å | θ = 3.2–28.3° |
c = 9.0173 (8) Å | µ = 0.20 mm−1 |
β = 95.799 (8)° | T = 295 K |
V = 946.17 (16) Å3 | Prism, colourless |
Z = 2 | 0.25 × 0.2 × 0.15 mm |
Xcalibur 3 diffractometer | Rint = 0.018 |
Graphite monochromator | θmax = 28.3°, θmin = 3.2° |
phi and ω scans | h = −7→6 |
6254 measured reflections | k = −24→23 |
4285 independent reflections | l = −12→11 |
2544 reflections with I > 2σ(I) |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.035 | w = 1/[σ2(Fo2) + (0.018P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.055 | (Δ/σ)max < 0.001 |
S = 1.01 | Δρmax = 0.35 e Å−3 |
4285 reflections | Δρmin = −0.17 e Å−3 |
248 parameters | Absolute structure: Flack x determined using 908 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
1 restraint | Absolute structure parameter: −0.02 (4) |
Primary atom site location: structure-invariant direct methods |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.36652 (11) | 0.60607 (4) | 0.42819 (7) | 0.05628 (19) | |
N4 | 0.7935 (4) | 0.72176 (13) | 0.4776 (2) | 0.0508 (5) | |
O2 | 0.2896 (3) | 0.62515 (12) | −0.08442 (19) | 0.0837 (6) | |
C11 | 0.8701 (5) | 0.44206 (18) | 0.6728 (3) | 0.0716 (9) | |
H11 | 0.997368 | 0.451200 | 0.621087 | 0.086* | |
N3 | 0.6869 (3) | 0.70046 (11) | 0.3383 (2) | 0.0483 (5) | |
O3 | 0.9198 (4) | 0.57769 (12) | 0.5526 (3) | 0.1050 (8) | |
C10 | 0.8512 (7) | 0.37557 (19) | 0.7430 (5) | 0.0943 (12) | |
H10 | 0.966230 | 0.340088 | 0.740841 | 0.113* | |
N2 | 0.7662 (4) | 0.73095 (12) | 0.2163 (3) | 0.0592 (6) | |
O1 | 0.1707 (3) | 0.58020 (10) | 0.12459 (19) | 0.0687 (6) | |
C9 | 0.6622 (8) | 0.36191 (19) | 0.8160 (4) | 0.0957 (12) | |
H9 | 0.649362 | 0.316911 | 0.864339 | 0.115* | |
N1 | 0.6394 (4) | 0.70367 (13) | 0.1026 (2) | 0.0622 (6) | |
C8 | 0.4936 (6) | 0.41267 (18) | 0.8193 (3) | 0.0800 (9) | |
H8 | 0.364350 | 0.402166 | 0.868084 | 0.096* | |
C7 | 0.5123 (5) | 0.48037 (14) | 0.7501 (3) | 0.0589 (7) | |
H7 | 0.395967 | 0.515363 | 0.752823 | 0.071* | |
C6 | 0.7023 (5) | 0.49584 (14) | 0.6778 (3) | 0.0499 (6) | |
C5 | 0.7399 (5) | 0.56704 (15) | 0.6064 (3) | 0.0529 (7) | |
C14 | −0.0157 (5) | 0.5406 (2) | 0.0433 (3) | 0.0818 (9) | |
H14A | 0.044129 | 0.505773 | −0.024936 | 0.098* | |
H14B | −0.117890 | 0.574749 | −0.013907 | 0.098* | |
C15 | −0.1415 (5) | 0.50110 (19) | 0.1526 (4) | 0.0909 (11) | |
H15A | −0.267320 | 0.474084 | 0.101443 | 0.136* | |
H15B | −0.038924 | 0.467386 | 0.208389 | 0.136* | |
H15C | −0.200264 | 0.536072 | 0.219372 | 0.136* | |
C19 | 0.8007 (4) | 0.71901 (17) | 0.7426 (3) | 0.0602 (7) | |
H19A | 0.720747 | 0.700856 | 0.824554 | 0.072* | |
H19B | 0.940185 | 0.689966 | 0.740126 | 0.072* | |
C12 | 0.8676 (5) | 0.79896 (18) | 0.7729 (3) | 0.0774 (9) | |
H12A | 0.954194 | 0.802957 | 0.870237 | 0.093* | |
H12B | 0.965394 | 0.815854 | 0.698876 | 0.093* | |
C18 | 0.6552 (6) | 0.84698 (17) | 0.7678 (4) | 0.0833 (10) | |
H18A | 0.700099 | 0.898134 | 0.784989 | 0.100* | |
H18B | 0.561634 | 0.832065 | 0.845682 | 0.100* | |
C17 | 0.5169 (5) | 0.83971 (15) | 0.6174 (3) | 0.0697 (8) | |
H17A | 0.380600 | 0.870654 | 0.614750 | 0.084* | |
H17B | 0.608726 | 0.856651 | 0.540201 | 0.084* | |
C16 | 0.4458 (4) | 0.76090 (13) | 0.5875 (3) | 0.0514 (7) | |
H16A | 0.364179 | 0.757671 | 0.488446 | 0.062* | |
H16B | 0.339679 | 0.746261 | 0.658346 | 0.062* | |
C3 | 0.6485 (4) | 0.70683 (14) | 0.5982 (2) | 0.0448 (6) | |
C4 | 0.5561 (4) | 0.62651 (13) | 0.5941 (2) | 0.0448 (6) | |
H4A | 0.466012 | 0.620596 | 0.679352 | 0.054* | |
C13 | 0.3082 (5) | 0.62070 (16) | 0.0483 (3) | 0.0588 (7) | |
C2 | 0.4797 (5) | 0.65724 (14) | 0.1501 (2) | 0.0501 (6) | |
C1 | 0.5114 (4) | 0.65376 (13) | 0.3023 (3) | 0.0452 (6) | |
H4 | 0.914 (5) | 0.6921 (15) | 0.495 (3) | 0.069 (10)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0583 (4) | 0.0631 (4) | 0.0490 (4) | −0.0158 (4) | 0.0131 (3) | 0.0044 (4) |
N4 | 0.0485 (13) | 0.0625 (15) | 0.0430 (13) | −0.0080 (12) | 0.0121 (11) | 0.0012 (11) |
O2 | 0.1033 (15) | 0.1071 (19) | 0.0405 (11) | 0.0101 (12) | 0.0068 (10) | −0.0045 (11) |
C11 | 0.0572 (19) | 0.056 (2) | 0.098 (2) | 0.0079 (16) | −0.0074 (17) | −0.0132 (18) |
N3 | 0.0588 (13) | 0.0491 (14) | 0.0397 (13) | −0.0044 (11) | 0.0171 (11) | 0.0054 (10) |
O3 | 0.0796 (14) | 0.0821 (17) | 0.167 (2) | 0.0246 (11) | 0.0776 (16) | 0.0360 (14) |
C10 | 0.072 (3) | 0.048 (2) | 0.156 (3) | 0.0110 (17) | −0.026 (2) | −0.011 (2) |
N2 | 0.0759 (15) | 0.0569 (15) | 0.0487 (13) | −0.0080 (12) | 0.0251 (13) | 0.0045 (11) |
O1 | 0.0769 (13) | 0.0750 (15) | 0.0523 (11) | −0.0086 (11) | −0.0037 (10) | −0.0120 (10) |
C9 | 0.091 (3) | 0.054 (2) | 0.132 (3) | −0.017 (2) | −0.037 (3) | 0.018 (2) |
N1 | 0.0823 (16) | 0.0585 (15) | 0.0492 (14) | 0.0034 (12) | 0.0243 (13) | 0.0048 (11) |
C8 | 0.084 (2) | 0.062 (2) | 0.093 (2) | −0.014 (2) | 0.0020 (17) | 0.0200 (19) |
C7 | 0.0652 (19) | 0.0485 (18) | 0.0632 (18) | −0.0043 (14) | 0.0076 (15) | 0.0032 (14) |
C6 | 0.0483 (16) | 0.0450 (17) | 0.0555 (16) | 0.0002 (13) | 0.0001 (14) | −0.0078 (13) |
C5 | 0.0527 (16) | 0.0560 (18) | 0.0527 (16) | 0.0050 (13) | 0.0189 (14) | 0.0048 (12) |
C14 | 0.079 (2) | 0.089 (3) | 0.075 (2) | −0.0019 (19) | −0.0061 (19) | −0.0233 (19) |
C15 | 0.075 (2) | 0.080 (2) | 0.115 (3) | −0.0035 (18) | −0.006 (2) | −0.013 (2) |
C19 | 0.0522 (16) | 0.080 (2) | 0.0483 (16) | 0.0017 (15) | 0.0054 (13) | 0.0008 (15) |
C12 | 0.071 (2) | 0.089 (3) | 0.071 (2) | −0.0135 (19) | −0.0028 (18) | −0.0224 (17) |
C18 | 0.089 (3) | 0.070 (2) | 0.092 (2) | −0.0146 (19) | 0.016 (2) | −0.0276 (18) |
C17 | 0.071 (2) | 0.0532 (19) | 0.086 (2) | 0.0013 (15) | 0.0174 (18) | −0.0036 (16) |
C16 | 0.0513 (15) | 0.0538 (18) | 0.0504 (15) | −0.0001 (13) | 0.0112 (13) | 0.0037 (12) |
C3 | 0.0442 (13) | 0.0495 (16) | 0.0423 (14) | −0.0010 (12) | 0.0126 (12) | 0.0041 (11) |
C4 | 0.0461 (14) | 0.0510 (18) | 0.0400 (13) | −0.0010 (12) | 0.0175 (11) | 0.0072 (11) |
C13 | 0.0751 (19) | 0.058 (2) | 0.0443 (17) | 0.0170 (16) | 0.0114 (16) | −0.0044 (15) |
C2 | 0.0634 (17) | 0.0482 (16) | 0.0403 (16) | 0.0029 (14) | 0.0131 (14) | −0.0009 (13) |
C1 | 0.0498 (15) | 0.0441 (15) | 0.0424 (14) | −0.0056 (12) | 0.0083 (12) | −0.0010 (12) |
S1—C4 | 1.806 (2) | C14—H14A | 0.9700 |
S1—C1 | 1.715 (2) | C14—H14B | 0.9700 |
N4—N3 | 1.398 (3) | C14—C15 | 1.472 (4) |
N4—C3 | 1.468 (3) | C15—H15A | 0.9600 |
N4—H4 | 0.88 (3) | C15—H15B | 0.9600 |
O2—C13 | 1.194 (3) | C15—H15C | 0.9600 |
C11—H11 | 0.9300 | C19—H19A | 0.9700 |
C11—C10 | 1.369 (4) | C19—H19B | 0.9700 |
C11—C6 | 1.383 (4) | C19—C12 | 1.516 (4) |
N3—N2 | 1.353 (3) | C19—C3 | 1.516 (3) |
N3—C1 | 1.341 (3) | C12—H12A | 0.9700 |
O3—C5 | 1.214 (3) | C12—H12B | 0.9700 |
C10—H10 | 0.9300 | C12—C18 | 1.509 (4) |
C10—C9 | 1.362 (5) | C18—H18A | 0.9700 |
N2—N1 | 1.300 (3) | C18—H18B | 0.9700 |
O1—C14 | 1.439 (3) | C18—C17 | 1.512 (4) |
O1—C13 | 1.328 (3) | C17—H17A | 0.9700 |
C9—H9 | 0.9300 | C17—H17B | 0.9700 |
C9—C8 | 1.348 (4) | C17—C16 | 1.502 (3) |
N1—C2 | 1.355 (3) | C16—H16A | 0.9700 |
C8—H8 | 0.9300 | C16—H16B | 0.9700 |
C8—C7 | 1.384 (4) | C16—C3 | 1.530 (3) |
C7—H7 | 0.9300 | C3—C4 | 1.549 (3) |
C7—C6 | 1.370 (4) | C4—H4A | 0.9800 |
C6—C5 | 1.467 (4) | C13—C2 | 1.447 (4) |
C5—C4 | 1.515 (3) | C2—C1 | 1.368 (3) |
C1—S1—C4 | 98.29 (11) | C3—C19—H19A | 108.7 |
N3—N4—C3 | 112.22 (18) | C3—C19—H19B | 108.7 |
N3—N4—H4 | 105.1 (18) | C19—C12—H12A | 109.6 |
C3—N4—H4 | 105.4 (17) | C19—C12—H12B | 109.6 |
C10—C11—H11 | 119.6 | H12A—C12—H12B | 108.1 |
C10—C11—C6 | 120.8 (3) | C18—C12—C19 | 110.4 (2) |
C6—C11—H11 | 119.6 | C18—C12—H12A | 109.6 |
N2—N3—N4 | 117.4 (2) | C18—C12—H12B | 109.6 |
C1—N3—N4 | 130.53 (19) | C12—C18—H18A | 109.7 |
C1—N3—N2 | 112.0 (2) | C12—C18—H18B | 109.7 |
C11—C10—H10 | 120.3 | C12—C18—C17 | 109.8 (3) |
C9—C10—C11 | 119.3 (3) | H18A—C18—H18B | 108.2 |
C9—C10—H10 | 120.3 | C17—C18—H18A | 109.7 |
N1—N2—N3 | 105.9 (2) | C17—C18—H18B | 109.7 |
C13—O1—C14 | 118.4 (2) | C18—C17—H17A | 109.5 |
C10—C9—H9 | 119.5 | C18—C17—H17B | 109.5 |
C8—C9—C10 | 120.9 (3) | H17A—C17—H17B | 108.1 |
C8—C9—H9 | 119.5 | C16—C17—C18 | 110.9 (2) |
N2—N1—C2 | 109.87 (19) | C16—C17—H17A | 109.5 |
C9—C8—H8 | 119.9 | C16—C17—H17B | 109.5 |
C9—C8—C7 | 120.2 (3) | C17—C16—H16A | 108.9 |
C7—C8—H8 | 119.9 | C17—C16—H16B | 108.9 |
C8—C7—H7 | 120.0 | C17—C16—C3 | 113.5 (2) |
C6—C7—C8 | 120.0 (3) | H16A—C16—H16B | 107.7 |
C6—C7—H7 | 120.0 | C3—C16—H16A | 108.9 |
C11—C6—C5 | 117.8 (3) | C3—C16—H16B | 108.9 |
C7—C6—C11 | 118.7 (3) | N4—C3—C19 | 106.19 (19) |
C7—C6—C5 | 123.5 (2) | N4—C3—C16 | 109.5 (2) |
O3—C5—C6 | 119.2 (2) | N4—C3—C4 | 112.32 (18) |
O3—C5—C4 | 119.4 (2) | C19—C3—C16 | 110.0 (2) |
C6—C5—C4 | 121.3 (2) | C19—C3—C4 | 109.21 (19) |
O1—C14—H14A | 110.2 | C16—C3—C4 | 109.50 (19) |
O1—C14—H14B | 110.2 | S1—C4—H4A | 107.2 |
O1—C14—C15 | 107.6 (2) | C5—C4—S1 | 106.53 (16) |
H14A—C14—H14B | 108.5 | C5—C4—C3 | 115.02 (19) |
C15—C14—H14A | 110.2 | C5—C4—H4A | 107.2 |
C15—C14—H14B | 110.2 | C3—C4—S1 | 113.23 (15) |
C14—C15—H15A | 109.5 | C3—C4—H4A | 107.2 |
C14—C15—H15B | 109.5 | O2—C13—O1 | 123.9 (3) |
C14—C15—H15C | 109.5 | O2—C13—C2 | 126.3 (3) |
H15A—C15—H15B | 109.5 | O1—C13—C2 | 109.8 (2) |
H15A—C15—H15C | 109.5 | N1—C2—C13 | 122.4 (2) |
H15B—C15—H15C | 109.5 | N1—C2—C1 | 108.6 (2) |
H19A—C19—H19B | 107.6 | C1—C2—C13 | 129.0 (2) |
C12—C19—H19A | 108.7 | N3—C1—S1 | 124.85 (18) |
C12—C19—H19B | 108.7 | N3—C1—C2 | 103.7 (2) |
C12—C19—C3 | 114.3 (2) | C2—C1—S1 | 131.4 (2) |
C20H24N4O4S | Dx = 1.320 Mg m−3 |
Mr = 416.49 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pca21 | Cell parameters from 2233 reflections |
a = 28.5394 (14) Å | θ = 2.7–27.0° |
b = 8.0288 (3) Å | µ = 0.19 mm−1 |
c = 9.1435 (4) Å | T = 295 K |
V = 2095.12 (16) Å3 | Block, light yellow |
Z = 4 | 0.25 × 0.2 × 0.15 mm |
F(000) = 880 |
Xcalibur 3 diffractometer | 2926 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
phi and ω scans | θmax = 27.1°, θmin = 2.5° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | h = −17→36 |
Tmin = 0.822, Tmax = 1.000 | k = −10→10 |
6492 measured reflections | l = −5→11 |
3439 independent reflections |
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.070P)2] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.040 | (Δ/σ)max < 0.001 |
wR(F2) = 0.112 | Δρmax = 0.22 e Å−3 |
S = 1.00 | Δρmin = −0.19 e Å−3 |
3439 reflections | Absolute structure: Flack x determined using 735 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
272 parameters | Absolute structure parameter: 0.04 (5) |
1 restraint |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.36348 (3) | 0.71255 (10) | 0.46005 (10) | 0.0492 (2) | |
N4 | 0.36707 (11) | 0.7878 (3) | 0.1100 (3) | 0.0444 (6) | |
C1 | 0.35711 (11) | 0.8968 (3) | 0.3637 (3) | 0.0384 (7) | |
N3 | 0.35821 (9) | 0.9092 (3) | 0.2163 (3) | 0.0402 (6) | |
O2 | 0.33641 (12) | 1.2673 (3) | 0.5873 (3) | 0.0718 (8) | |
N2 | 0.35044 (10) | 1.0690 (3) | 0.1705 (3) | 0.0472 (7) | |
O1 | 0.33760 (10) | 0.9973 (3) | 0.6510 (3) | 0.0571 (7) | |
O3 | 0.45378 (9) | 0.7191 (3) | 0.2518 (4) | 0.0673 (8) | |
C16 | 0.37673 (12) | 0.5009 (4) | 0.0447 (4) | 0.0468 (8) | |
H16B | 0.409392 | 0.527921 | 0.027425 | 0.056* | |
H16A | 0.375257 | 0.386855 | 0.079373 | 0.056* | |
N1 | 0.34453 (10) | 1.1582 (3) | 0.2878 (3) | 0.0487 (6) | |
C5 | 0.43595 (11) | 0.5895 (4) | 0.2961 (4) | 0.0467 (7) | |
C7 | 0.44955 (11) | 0.3132 (4) | 0.4193 (4) | 0.0526 (9) | |
H7 | 0.419895 | 0.319820 | 0.461145 | 0.063* | |
C4 | 0.38270 (11) | 0.5783 (3) | 0.3105 (4) | 0.0412 (7) | |
C3 | 0.35734 (11) | 0.6170 (3) | 0.1636 (4) | 0.0395 (7) | |
C2 | 0.34765 (11) | 1.0583 (4) | 0.4079 (4) | 0.0426 (7) | |
C13 | 0.34010 (12) | 1.1229 (4) | 0.5558 (4) | 0.0469 (8) | |
C14 | 0.32623 (14) | 1.0351 (5) | 0.8032 (4) | 0.0592 (9) | |
H14B | 0.339278 | 1.142591 | 0.829565 | 0.071* | |
H14A | 0.339951 | 0.951550 | 0.866715 | 0.071* | |
C17 | 0.34998 (16) | 0.5143 (5) | −0.0985 (5) | 0.0652 (11) | |
H17B | 0.354257 | 0.624772 | −0.139336 | 0.078* | |
H17A | 0.362346 | 0.434085 | −0.167790 | 0.078* | |
C6 | 0.46502 (11) | 0.4411 (4) | 0.3287 (4) | 0.0446 (7) | |
C8 | 0.47782 (11) | 0.1751 (4) | 0.4486 (5) | 0.0625 (10) | |
H8 | 0.467273 | 0.090747 | 0.510040 | 0.075* | |
C20 | 0.30446 (10) | 0.5909 (4) | 0.1820 (4) | 0.0478 (8) | |
H20B | 0.298953 | 0.482636 | 0.225788 | 0.057* | |
H20A | 0.292267 | 0.674762 | 0.248284 | 0.057* | |
C18 | 0.29826 (16) | 0.4821 (5) | −0.0752 (6) | 0.0801 (14) | |
H18B | 0.293810 | 0.368436 | −0.041939 | 0.096* | |
H18A | 0.281765 | 0.495076 | −0.167221 | 0.096* | |
C19 | 0.27799 (14) | 0.6014 (5) | 0.0368 (5) | 0.0681 (11) | |
H19B | 0.245232 | 0.574834 | 0.052930 | 0.082* | |
H19A | 0.279755 | 0.714218 | −0.000664 | 0.082* | |
C11 | 0.50950 (11) | 0.4284 (4) | 0.2654 (5) | 0.0602 (10) | |
H11 | 0.520498 | 0.512528 | 0.204470 | 0.072* | |
O4 | 0.55220 (10) | 0.0387 (4) | 0.4082 (5) | 0.0987 (13) | |
C9 | 0.52138 (13) | 0.1658 (5) | 0.3856 (6) | 0.0672 (11) | |
C10 | 0.53684 (13) | 0.2916 (5) | 0.2933 (6) | 0.0722 (12) | |
H10 | 0.566188 | 0.283053 | 0.249744 | 0.087* | |
C15 | 0.27435 (16) | 1.0380 (6) | 0.8236 (6) | 0.0812 (13) | |
H15B | 0.261339 | 1.130770 | 0.771299 | 0.122* | |
H15A | 0.267212 | 1.048667 | 0.925773 | 0.122* | |
H15C | 0.261125 | 0.936319 | 0.786839 | 0.122* | |
C12 | 0.53770 (17) | −0.0976 (6) | 0.4963 (10) | 0.117 (3) | |
H12C | 0.511001 | −0.150343 | 0.452321 | 0.176* | |
H12B | 0.529452 | −0.057995 | 0.591976 | 0.176* | |
H12A | 0.562837 | −0.176519 | 0.504190 | 0.176* | |
H4 | 0.3983 (11) | 0.801 (3) | 0.086 (4) | 0.037 (9)* | |
H4A | 0.3710 (10) | 0.468 (4) | 0.346 (4) | 0.035 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0752 (5) | 0.0374 (4) | 0.0352 (4) | 0.0037 (4) | 0.0008 (4) | 0.0049 (4) |
N4 | 0.0679 (19) | 0.0311 (13) | 0.0342 (13) | −0.0018 (12) | 0.0043 (13) | −0.0045 (12) |
C1 | 0.0505 (16) | 0.0305 (14) | 0.0342 (15) | −0.0022 (12) | 0.0014 (13) | −0.0019 (13) |
N3 | 0.0612 (15) | 0.0267 (12) | 0.0328 (13) | −0.0008 (10) | 0.0001 (12) | −0.0023 (11) |
O2 | 0.126 (2) | 0.0362 (13) | 0.0536 (18) | −0.0062 (13) | 0.0154 (17) | −0.0137 (12) |
N2 | 0.0729 (18) | 0.0250 (12) | 0.0436 (16) | 0.0001 (11) | 0.0017 (14) | 0.0043 (12) |
O1 | 0.0946 (18) | 0.0437 (12) | 0.0330 (13) | −0.0003 (11) | 0.0071 (13) | −0.0035 (11) |
O3 | 0.0633 (14) | 0.0502 (14) | 0.089 (2) | −0.0177 (11) | −0.0049 (15) | 0.0155 (15) |
C16 | 0.0567 (18) | 0.0350 (16) | 0.049 (2) | 0.0004 (13) | 0.0049 (16) | −0.0081 (15) |
N1 | 0.0741 (17) | 0.0290 (11) | 0.0429 (15) | −0.0039 (12) | 0.0037 (15) | −0.0022 (13) |
C5 | 0.0544 (17) | 0.0414 (15) | 0.0441 (17) | −0.0089 (13) | −0.0056 (17) | 0.0018 (15) |
C7 | 0.0447 (17) | 0.0556 (19) | 0.058 (2) | −0.0023 (13) | −0.0017 (16) | 0.0133 (17) |
C4 | 0.0526 (16) | 0.0257 (13) | 0.0454 (18) | −0.0004 (12) | 0.0006 (15) | 0.0024 (13) |
C3 | 0.0548 (16) | 0.0242 (13) | 0.0396 (16) | 0.0002 (11) | −0.0017 (14) | −0.0037 (14) |
C2 | 0.0545 (17) | 0.0353 (15) | 0.0380 (16) | −0.0082 (12) | −0.0002 (15) | −0.0010 (14) |
C13 | 0.064 (2) | 0.0365 (16) | 0.0405 (17) | −0.0057 (14) | 0.0045 (16) | −0.0067 (15) |
C14 | 0.084 (2) | 0.057 (2) | 0.0366 (18) | −0.0046 (17) | 0.003 (2) | −0.0085 (17) |
C17 | 0.085 (3) | 0.056 (2) | 0.054 (2) | 0.0049 (19) | −0.005 (2) | −0.022 (2) |
C6 | 0.0413 (15) | 0.0506 (17) | 0.0420 (18) | −0.0069 (13) | −0.0066 (14) | 0.0035 (15) |
C8 | 0.0494 (19) | 0.063 (2) | 0.075 (3) | 0.0013 (14) | −0.014 (2) | 0.021 (2) |
C20 | 0.0496 (17) | 0.0383 (16) | 0.055 (2) | 0.0042 (13) | −0.0009 (16) | −0.0020 (16) |
C18 | 0.083 (3) | 0.083 (3) | 0.074 (3) | 0.003 (2) | −0.021 (2) | −0.033 (3) |
C19 | 0.062 (2) | 0.068 (2) | 0.074 (3) | 0.0071 (18) | −0.016 (2) | −0.003 (2) |
C11 | 0.0471 (17) | 0.072 (2) | 0.061 (3) | −0.0054 (16) | −0.0025 (17) | 0.015 (2) |
O4 | 0.0584 (16) | 0.092 (2) | 0.146 (4) | 0.0247 (14) | −0.0116 (19) | 0.030 (2) |
C9 | 0.050 (2) | 0.068 (2) | 0.083 (3) | 0.0096 (17) | −0.018 (2) | 0.004 (2) |
C10 | 0.0424 (18) | 0.090 (3) | 0.084 (3) | 0.0054 (17) | 0.005 (2) | 0.013 (3) |
C15 | 0.086 (3) | 0.089 (3) | 0.069 (3) | −0.016 (2) | 0.012 (3) | −0.002 (3) |
C12 | 0.081 (3) | 0.074 (3) | 0.197 (8) | 0.014 (2) | −0.046 (4) | 0.040 (4) |
S1—C1 | 1.731 (3) | C14—H14B | 0.9700 |
S1—C4 | 1.826 (3) | C14—H14A | 0.9700 |
N4—N3 | 1.399 (4) | C17—C18 | 1.514 (6) |
N4—C3 | 1.482 (4) | C17—H17B | 0.9700 |
N4—H4 | 0.92 (3) | C17—H17A | 0.9700 |
C1—N3 | 1.352 (4) | C6—C11 | 1.399 (5) |
C1—C2 | 1.385 (4) | C8—C9 | 1.372 (5) |
N3—N2 | 1.368 (3) | C8—H8 | 0.9300 |
O2—C13 | 1.199 (4) | C20—C19 | 1.530 (6) |
N2—N1 | 1.301 (4) | C20—H20B | 0.9700 |
O1—C13 | 1.334 (4) | C20—H20A | 0.9700 |
O1—C14 | 1.461 (4) | C18—C19 | 1.517 (6) |
O3—C5 | 1.227 (4) | C18—H18B | 0.9700 |
C16—C17 | 1.520 (6) | C18—H18A | 0.9700 |
C16—C3 | 1.535 (4) | C19—H19B | 0.9700 |
C16—H16B | 0.9700 | C19—H19A | 0.9700 |
C16—H16A | 0.9700 | C11—C10 | 1.371 (5) |
N1—C2 | 1.362 (4) | C11—H11 | 0.9300 |
C5—C6 | 1.482 (5) | O4—C9 | 1.363 (4) |
C5—C4 | 1.528 (5) | O4—C12 | 1.421 (7) |
C7—C6 | 1.391 (5) | C9—C10 | 1.389 (6) |
C7—C8 | 1.397 (5) | C10—H10 | 0.9300 |
C7—H7 | 0.9300 | C15—H15B | 0.9600 |
C4—C3 | 1.557 (5) | C15—H15A | 0.9600 |
C4—H4A | 1.00 (3) | C15—H15C | 0.9600 |
C3—C20 | 1.533 (4) | C12—H12C | 0.9600 |
C2—C13 | 1.464 (5) | C12—H12B | 0.9600 |
C14—C15 | 1.492 (6) | C12—H12A | 0.9600 |
C1—S1—C4 | 98.91 (15) | C16—C17—H17B | 109.5 |
N3—N4—C3 | 112.4 (3) | C18—C17—H17A | 109.5 |
N3—N4—H4 | 105.0 (19) | C16—C17—H17A | 109.5 |
C3—N4—H4 | 111.2 (18) | H17B—C17—H17A | 108.1 |
N3—C1—C2 | 103.1 (3) | C7—C6—C11 | 118.7 (3) |
N3—C1—S1 | 124.6 (2) | C7—C6—C5 | 122.4 (3) |
C2—C1—S1 | 132.2 (3) | C11—C6—C5 | 118.9 (3) |
C1—N3—N2 | 111.7 (3) | C9—C8—C7 | 119.1 (4) |
C1—N3—N4 | 130.2 (3) | C9—C8—H8 | 120.5 |
N2—N3—N4 | 118.0 (3) | C7—C8—H8 | 120.5 |
N1—N2—N3 | 106.5 (3) | C19—C20—C3 | 112.5 (3) |
C13—O1—C14 | 118.4 (3) | C19—C20—H20B | 109.1 |
C17—C16—C3 | 112.7 (3) | C3—C20—H20B | 109.1 |
C17—C16—H16B | 109.0 | C19—C20—H20A | 109.1 |
C3—C16—H16B | 109.0 | C3—C20—H20A | 109.1 |
C17—C16—H16A | 109.0 | H20B—C20—H20A | 107.8 |
C3—C16—H16A | 109.0 | C17—C18—C19 | 111.0 (3) |
H16B—C16—H16A | 107.8 | C17—C18—H18B | 109.4 |
N2—N1—C2 | 109.4 (2) | C19—C18—H18B | 109.4 |
O3—C5—C6 | 121.1 (3) | C17—C18—H18A | 109.4 |
O3—C5—C4 | 119.4 (3) | C19—C18—H18A | 109.4 |
C6—C5—C4 | 119.5 (3) | H18B—C18—H18A | 108.0 |
C6—C7—C8 | 121.1 (3) | C18—C19—C20 | 111.3 (3) |
C6—C7—H7 | 119.5 | C18—C19—H19B | 109.4 |
C8—C7—H7 | 119.5 | C20—C19—H19B | 109.4 |
C5—C4—C3 | 112.1 (3) | C18—C19—H19A | 109.4 |
C5—C4—S1 | 109.2 (2) | C20—C19—H19A | 109.4 |
C3—C4—S1 | 112.88 (19) | H19B—C19—H19A | 108.0 |
C5—C4—H4A | 114.3 (17) | C10—C11—C6 | 119.8 (4) |
C3—C4—H4A | 107.6 (19) | C10—C11—H11 | 120.1 |
S1—C4—H4A | 100.3 (18) | C6—C11—H11 | 120.1 |
N4—C3—C20 | 110.3 (2) | C9—O4—C12 | 118.3 (4) |
N4—C3—C16 | 105.1 (3) | O4—C9—C8 | 124.2 (4) |
C20—C3—C16 | 110.5 (3) | O4—C9—C10 | 115.6 (4) |
N4—C3—C4 | 112.5 (2) | C8—C9—C10 | 120.2 (3) |
C20—C3—C4 | 109.6 (3) | C11—C10—C9 | 121.0 (4) |
C16—C3—C4 | 108.8 (2) | C11—C10—H10 | 119.5 |
N1—C2—C1 | 109.2 (3) | C9—C10—H10 | 119.5 |
N1—C2—C13 | 121.8 (3) | C14—C15—H15B | 109.5 |
C1—C2—C13 | 129.0 (3) | C14—C15—H15A | 109.5 |
O2—C13—O1 | 124.7 (3) | H15B—C15—H15A | 109.5 |
O2—C13—C2 | 125.3 (3) | C14—C15—H15C | 109.5 |
O1—C13—C2 | 110.1 (3) | H15B—C15—H15C | 109.5 |
O1—C14—C15 | 110.0 (3) | H15A—C15—H15C | 109.5 |
O1—C14—H14B | 109.7 | O4—C12—H12C | 109.5 |
C15—C14—H14B | 109.7 | O4—C12—H12B | 109.5 |
O1—C14—H14A | 109.7 | H12C—C12—H12B | 109.5 |
C15—C14—H14A | 109.7 | O4—C12—H12A | 109.5 |
H14B—C14—H14A | 108.2 | H12C—C12—H12A | 109.5 |
C18—C17—C16 | 110.9 (4) | H12B—C12—H12A | 109.5 |
C18—C17—H17B | 109.5 | ||
C4—S1—C1—N3 | 11.0 (3) | N3—C1—C2—C13 | 176.9 (3) |
C4—S1—C1—C2 | −172.9 (3) | S1—C1—C2—C13 | 0.2 (6) |
C2—C1—N3—N2 | 0.6 (4) | C14—O1—C13—O2 | 4.7 (5) |
S1—C1—N3—N2 | 177.7 (2) | C14—O1—C13—C2 | −175.0 (3) |
C2—C1—N3—N4 | 178.7 (3) | N1—C2—C13—O2 | −9.6 (6) |
S1—C1—N3—N4 | −4.3 (5) | C1—C2—C13—O2 | 172.5 (3) |
C3—N4—N3—C1 | 23.5 (5) | N1—C2—C13—O1 | 170.0 (3) |
C3—N4—N3—N2 | −158.5 (3) | C1—C2—C13—O1 | −7.8 (5) |
C1—N3—N2—N1 | 0.1 (4) | C13—O1—C14—C15 | 87.2 (4) |
N4—N3—N2—N1 | −178.2 (3) | C3—C16—C17—C18 | −55.7 (4) |
N3—N2—N1—C2 | −0.9 (3) | C8—C7—C6—C11 | 0.7 (5) |
O3—C5—C4—C3 | 56.5 (4) | C8—C7—C6—C5 | −179.7 (4) |
C6—C5—C4—C3 | −120.4 (3) | O3—C5—C6—C7 | 159.5 (4) |
O3—C5—C4—S1 | −69.4 (4) | C4—C5—C6—C7 | −23.7 (5) |
C6—C5—C4—S1 | 113.7 (3) | O3—C5—C6—C11 | −20.9 (5) |
C1—S1—C4—C5 | 87.5 (2) | C4—C5—C6—C11 | 155.9 (3) |
C1—S1—C4—C3 | −37.9 (2) | C6—C7—C8—C9 | −0.5 (6) |
N3—N4—C3—C20 | 70.4 (3) | N4—C3—C20—C19 | 64.1 (4) |
N3—N4—C3—C16 | −170.6 (3) | C16—C3—C20—C19 | −51.6 (4) |
N3—N4—C3—C4 | −52.4 (3) | C4—C3—C20—C19 | −171.5 (3) |
C17—C16—C3—N4 | −66.4 (4) | C16—C17—C18—C19 | 57.1 (5) |
C17—C16—C3—C20 | 52.5 (4) | C17—C18—C19—C20 | −56.5 (5) |
C17—C16—C3—C4 | 172.9 (3) | C3—C20—C19—C18 | 54.3 (5) |
C5—C4—C3—N4 | −61.1 (3) | C7—C6—C11—C10 | 0.0 (6) |
S1—C4—C3—N4 | 62.7 (3) | C5—C6—C11—C10 | −179.6 (4) |
C5—C4—C3—C20 | 175.8 (2) | C12—O4—C9—C8 | 3.5 (7) |
S1—C4—C3—C20 | −60.5 (3) | C12—O4—C9—C10 | −177.2 (5) |
C5—C4—C3—C16 | 54.9 (3) | C7—C8—C9—O4 | 178.9 (4) |
S1—C4—C3—C16 | 178.6 (2) | C7—C8—C9—C10 | −0.4 (7) |
N2—N1—C2—C1 | 1.4 (4) | C6—C11—C10—C9 | −1.0 (7) |
N2—N1—C2—C13 | −176.9 (3) | O4—C9—C10—C11 | −178.2 (4) |
N3—C1—C2—N1 | −1.2 (4) | C8—C9—C10—C11 | 1.1 (7) |
S1—C1—C2—N1 | −177.9 (3) |
C17H20N4O3S | F(000) = 760 |
Mr = 360.43 | Dx = 1.349 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.0154 (3) Å | Cell parameters from 2433 reflections |
b = 14.2211 (11) Å | θ = 2.6–28.0° |
c = 15.9349 (7) Å | µ = 0.21 mm−1 |
β = 102.337 (4)° | T = 295 K |
V = 1774.45 (17) Å3 | Prism, colourless |
Z = 4 | 0.25 × 0.2 × 0.15 mm |
Xcalibur 3 diffractometer | 2950 reflections with I > 2σ(I) |
Detector resolution: 15.9555 pixels mm-1 | Rint = 0.029 |
ω scans | θmax = 28.3°, θmin = 2.6° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | h = −10→10 |
Tmin = 0.947, Tmax = 1.000 | k = −18→9 |
8945 measured reflections | l = −21→14 |
4411 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.045 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.113 | w = 1/[σ2(Fo2) + (0.0428P)2 + 0.3794P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
4411 reflections | Δρmax = 0.21 e Å−3 |
238 parameters | Δρmin = −0.24 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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.50827 (6) | 0.22721 (4) | 0.01390 (3) | 0.05234 (17) | |
C4 | 0.6010 (2) | 0.26169 (14) | −0.07639 (11) | 0.0386 (4) | |
N1 | 0.02928 (17) | 0.16111 (12) | −0.08035 (10) | 0.0458 (4) | |
O1 | −0.00287 (16) | 0.12860 (13) | 0.08540 (9) | 0.0624 (4) | |
N3 | 0.25078 (16) | 0.20179 (11) | −0.12616 (9) | 0.0387 (4) | |
C3 | 0.5292 (2) | 0.20261 (14) | −0.15855 (12) | 0.0423 (4) | |
N4 | 0.34350 (17) | 0.21692 (15) | −0.18997 (10) | 0.0440 (4) | |
O2 | 0.27457 (18) | 0.15983 (13) | 0.13615 (9) | 0.0655 (5) | |
N2 | 0.08279 (16) | 0.17734 (13) | −0.15086 (10) | 0.0463 (4) | |
O3 | 0.43032 (15) | 0.39760 (11) | −0.10475 (11) | 0.0676 (5) | |
C17 | 0.6082 (2) | 0.23682 (18) | −0.23221 (12) | 0.0553 (6) | |
H17A | 0.579393 | 0.301730 | −0.243888 | 0.083* | |
H17B | 0.564743 | 0.199979 | −0.282620 | 0.083* | |
H17C | 0.730099 | 0.230270 | −0.216419 | 0.083* | |
C1 | 0.30372 (19) | 0.20152 (14) | −0.04058 (11) | 0.0384 (4) | |
C5 | 0.5753 (2) | 0.36639 (14) | −0.09285 (12) | 0.0423 (4) | |
C13 | 0.1525 (2) | 0.15400 (15) | 0.07757 (13) | 0.0472 (5) | |
C9 | 0.9843 (2) | 0.54966 (16) | −0.12010 (11) | 0.0484 (5) | |
C6 | 0.72125 (19) | 0.42822 (13) | −0.09868 (10) | 0.0369 (4) | |
C10 | 1.0153 (2) | 0.45553 (16) | −0.10392 (12) | 0.0469 (5) | |
H10 | 1.125065 | 0.432148 | −0.100003 | 0.056* | |
C2 | 0.1604 (2) | 0.17345 (14) | −0.01173 (11) | 0.0409 (4) | |
C16 | 0.5654 (2) | 0.09863 (16) | −0.14211 (15) | 0.0599 (6) | |
H16A | 0.686219 | 0.089120 | −0.123424 | 0.090* | |
H16B | 0.524214 | 0.063962 | −0.194098 | 0.090* | |
H16C | 0.508610 | 0.077087 | −0.098397 | 0.090* | |
C7 | 0.6911 (2) | 0.52377 (15) | −0.11324 (12) | 0.0482 (5) | |
H7 | 0.582126 | 0.547719 | −0.115878 | 0.058* | |
C14 | −0.0201 (3) | 0.0980 (2) | 0.17049 (14) | 0.0732 (8) | |
H14A | −0.004393 | 0.150829 | 0.209896 | 0.088* | |
H14B | 0.065166 | 0.050716 | 0.192637 | 0.088* | |
C11 | 0.8864 (2) | 0.39512 (15) | −0.09341 (12) | 0.0431 (4) | |
H11 | 0.910296 | 0.331712 | −0.082695 | 0.052* | |
C12 | 1.1244 (3) | 0.6148 (2) | −0.13432 (15) | 0.0740 (8) | |
H12A | 1.233299 | 0.585176 | −0.114247 | 0.111* | |
H12B | 1.119913 | 0.672236 | −0.103252 | 0.111* | |
H12C | 1.109229 | 0.628345 | −0.194493 | 0.111* | |
C15 | −0.1919 (3) | 0.05879 (18) | 0.16181 (15) | 0.0638 (6) | |
H15A | −0.274969 | 0.107703 | 0.145378 | 0.096* | |
H15B | −0.203474 | 0.032372 | 0.215708 | 0.096* | |
H15C | −0.209781 | 0.010573 | 0.118643 | 0.096* | |
C8 | 0.8204 (3) | 0.58335 (16) | −0.12379 (13) | 0.0550 (5) | |
H8 | 0.797663 | 0.647010 | −0.133527 | 0.066* | |
H4A | 0.714 (2) | 0.2460 (13) | −0.0590 (11) | 0.041 (5)* | |
H4 | 0.325 (2) | 0.2727 (15) | −0.2042 (13) | 0.043 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0366 (2) | 0.0798 (4) | 0.0373 (2) | −0.0182 (2) | 0.00045 (17) | 0.0070 (2) |
C4 | 0.0257 (8) | 0.0481 (12) | 0.0413 (9) | −0.0022 (7) | 0.0054 (6) | 0.0042 (8) |
N1 | 0.0308 (7) | 0.0564 (11) | 0.0506 (9) | −0.0038 (7) | 0.0100 (6) | −0.0008 (8) |
O1 | 0.0477 (8) | 0.0929 (13) | 0.0503 (8) | −0.0160 (7) | 0.0185 (6) | 0.0067 (8) |
N3 | 0.0262 (6) | 0.0508 (10) | 0.0381 (7) | −0.0037 (6) | 0.0046 (5) | 0.0015 (7) |
C3 | 0.0292 (8) | 0.0510 (12) | 0.0465 (10) | −0.0017 (8) | 0.0075 (7) | −0.0023 (9) |
N4 | 0.0311 (7) | 0.0614 (13) | 0.0391 (8) | −0.0026 (7) | 0.0066 (6) | 0.0047 (8) |
O2 | 0.0547 (8) | 0.0902 (13) | 0.0484 (8) | −0.0222 (8) | 0.0041 (7) | 0.0056 (8) |
N2 | 0.0263 (7) | 0.0619 (12) | 0.0484 (9) | −0.0028 (7) | 0.0030 (6) | −0.0017 (8) |
O3 | 0.0320 (7) | 0.0611 (11) | 0.1126 (13) | 0.0067 (6) | 0.0221 (7) | 0.0039 (9) |
C17 | 0.0416 (10) | 0.0794 (17) | 0.0483 (11) | −0.0062 (10) | 0.0170 (8) | −0.0062 (11) |
C1 | 0.0306 (8) | 0.0450 (11) | 0.0383 (9) | −0.0047 (7) | 0.0046 (7) | 0.0013 (8) |
C5 | 0.0310 (8) | 0.0495 (12) | 0.0480 (10) | 0.0000 (8) | 0.0117 (7) | −0.0012 (9) |
C13 | 0.0450 (10) | 0.0475 (13) | 0.0510 (11) | −0.0077 (8) | 0.0147 (9) | 0.0024 (10) |
C9 | 0.0472 (10) | 0.0575 (14) | 0.0373 (9) | −0.0163 (9) | 0.0020 (8) | 0.0044 (9) |
C6 | 0.0316 (8) | 0.0421 (11) | 0.0367 (8) | −0.0007 (7) | 0.0069 (6) | −0.0006 (8) |
C10 | 0.0324 (8) | 0.0612 (14) | 0.0481 (10) | −0.0054 (8) | 0.0106 (7) | −0.0003 (10) |
C2 | 0.0337 (8) | 0.0448 (12) | 0.0446 (10) | −0.0032 (7) | 0.0092 (7) | 0.0004 (9) |
C16 | 0.0455 (11) | 0.0517 (14) | 0.0807 (15) | −0.0015 (9) | 0.0096 (10) | −0.0081 (12) |
C7 | 0.0387 (9) | 0.0495 (13) | 0.0544 (11) | 0.0047 (8) | 0.0051 (8) | 0.0003 (10) |
C14 | 0.0659 (14) | 0.107 (2) | 0.0498 (12) | −0.0202 (14) | 0.0192 (10) | 0.0143 (13) |
C11 | 0.0342 (8) | 0.0433 (12) | 0.0527 (11) | 0.0003 (8) | 0.0113 (7) | 0.0006 (9) |
C12 | 0.0693 (14) | 0.088 (2) | 0.0611 (13) | −0.0377 (13) | 0.0048 (11) | 0.0158 (14) |
C15 | 0.0595 (13) | 0.0705 (17) | 0.0665 (13) | 0.0012 (11) | 0.0249 (10) | 0.0161 (13) |
C8 | 0.0585 (12) | 0.0438 (13) | 0.0567 (12) | −0.0062 (10) | −0.0011 (9) | 0.0050 (10) |
S1—C1 | 1.7225 (16) | C9—C10 | 1.376 (3) |
S1—C4 | 1.8218 (17) | C9—C8 | 1.388 (3) |
C4—C5 | 1.518 (3) | C9—C12 | 1.510 (3) |
C4—C3 | 1.559 (3) | C6—C11 | 1.391 (2) |
C4—H4A | 0.920 (18) | C6—C7 | 1.391 (3) |
N1—N2 | 1.306 (2) | C10—C11 | 1.381 (2) |
N1—C2 | 1.356 (2) | C10—H10 | 0.9300 |
O1—C13 | 1.328 (2) | C16—H16A | 0.9600 |
O1—C14 | 1.458 (2) | C16—H16B | 0.9600 |
N3—C1 | 1.339 (2) | C16—H16C | 0.9600 |
N3—N2 | 1.3647 (18) | C7—C8 | 1.377 (3) |
N3—N4 | 1.398 (2) | C7—H7 | 0.9300 |
C3—N4 | 1.480 (2) | C14—C15 | 1.464 (3) |
C3—C16 | 1.519 (3) | C14—H14A | 0.9700 |
C3—C17 | 1.527 (2) | C14—H14B | 0.9700 |
N4—H4 | 0.83 (2) | C11—H11 | 0.9300 |
O2—C13 | 1.202 (2) | C12—H12A | 0.9600 |
O3—C5 | 1.220 (2) | C12—H12B | 0.9600 |
C17—H17A | 0.9600 | C12—H12C | 0.9600 |
C17—H17B | 0.9600 | C15—H15A | 0.9600 |
C17—H17C | 0.9600 | C15—H15B | 0.9600 |
C1—C2 | 1.384 (2) | C15—H15C | 0.9600 |
C5—C6 | 1.482 (2) | C8—H8 | 0.9300 |
C13—C2 | 1.464 (3) | ||
C1—S1—C4 | 99.44 (8) | C11—C6—C5 | 123.33 (17) |
C5—C4—C3 | 111.80 (15) | C7—C6—C5 | 118.59 (15) |
C5—C4—S1 | 109.71 (12) | C9—C10—C11 | 121.20 (17) |
C3—C4—S1 | 112.27 (12) | C9—C10—H10 | 119.4 |
C5—C4—H4A | 112.2 (12) | C11—C10—H10 | 119.4 |
C3—C4—H4A | 106.7 (11) | N1—C2—C1 | 108.94 (15) |
S1—C4—H4A | 103.9 (11) | N1—C2—C13 | 124.90 (15) |
N2—N1—C2 | 109.29 (13) | C1—C2—C13 | 126.05 (15) |
C13—O1—C14 | 116.46 (15) | C3—C16—H16A | 109.5 |
C1—N3—N2 | 111.80 (13) | C3—C16—H16B | 109.5 |
C1—N3—N4 | 129.72 (13) | H16A—C16—H16B | 109.5 |
N2—N3—N4 | 118.33 (13) | C3—C16—H16C | 109.5 |
N4—C3—C16 | 109.47 (16) | H16A—C16—H16C | 109.5 |
N4—C3—C17 | 104.38 (15) | H16B—C16—H16C | 109.5 |
C16—C3—C17 | 110.35 (17) | C8—C7—C6 | 120.86 (17) |
N4—C3—C4 | 111.95 (15) | C8—C7—H7 | 119.6 |
C16—C3—C4 | 110.94 (16) | C6—C7—H7 | 119.6 |
C17—C3—C4 | 109.56 (15) | O1—C14—C15 | 107.44 (17) |
N3—N4—C3 | 112.67 (14) | O1—C14—H14A | 110.2 |
N3—N4—H4 | 104.8 (14) | C15—C14—H14A | 110.2 |
C3—N4—H4 | 109.2 (13) | O1—C14—H14B | 110.2 |
N1—N2—N3 | 106.39 (13) | C15—C14—H14B | 110.2 |
C3—C17—H17A | 109.5 | H14A—C14—H14B | 108.5 |
C3—C17—H17B | 109.5 | C10—C11—C6 | 120.61 (19) |
H17A—C17—H17B | 109.5 | C10—C11—H11 | 119.7 |
C3—C17—H17C | 109.5 | C6—C11—H11 | 119.7 |
H17A—C17—H17C | 109.5 | C9—C12—H12A | 109.5 |
H17B—C17—H17C | 109.5 | C9—C12—H12B | 109.5 |
N3—C1—C2 | 103.54 (14) | H12A—C12—H12B | 109.5 |
N3—C1—S1 | 124.97 (12) | C9—C12—H12C | 109.5 |
C2—C1—S1 | 131.45 (14) | H12A—C12—H12C | 109.5 |
O3—C5—C6 | 120.84 (18) | H12B—C12—H12C | 109.5 |
O3—C5—C4 | 118.23 (16) | C14—C15—H15A | 109.5 |
C6—C5—C4 | 120.85 (14) | C14—C15—H15B | 109.5 |
O2—C13—O1 | 124.74 (18) | H15A—C15—H15B | 109.5 |
O2—C13—C2 | 123.01 (16) | C14—C15—H15C | 109.5 |
O1—C13—C2 | 112.25 (16) | H15A—C15—H15C | 109.5 |
C10—C9—C8 | 118.38 (17) | H15B—C15—H15C | 109.5 |
C10—C9—C12 | 120.97 (19) | C7—C8—C9 | 120.9 (2) |
C8—C9—C12 | 120.6 (2) | C7—C8—H8 | 119.6 |
C11—C6—C7 | 118.04 (16) | C9—C8—H8 | 119.6 |
C1—S1—C4—C5 | 89.15 (13) | C14—O1—C13—C2 | 173.7 (2) |
C1—S1—C4—C3 | −35.81 (15) | O3—C5—C6—C11 | −174.04 (18) |
C5—C4—C3—N4 | −60.68 (19) | C4—C5—C6—C11 | 2.8 (3) |
S1—C4—C3—N4 | 63.12 (19) | O3—C5—C6—C7 | 3.6 (3) |
C5—C4—C3—C16 | 176.70 (14) | C4—C5—C6—C7 | −179.54 (17) |
S1—C4—C3—C16 | −59.50 (17) | C8—C9—C10—C11 | 1.4 (3) |
C5—C4—C3—C17 | 54.63 (19) | C12—C9—C10—C11 | −178.05 (18) |
S1—C4—C3—C17 | 178.42 (13) | N2—N1—C2—C1 | 1.7 (2) |
C1—N3—N4—C3 | 19.7 (3) | N2—N1—C2—C13 | −174.70 (19) |
N2—N3—N4—C3 | −155.47 (16) | N3—C1—C2—N1 | −1.7 (2) |
C16—C3—N4—N3 | 70.4 (2) | S1—C1—C2—N1 | −179.43 (16) |
C17—C3—N4—N3 | −171.51 (17) | N3—C1—C2—C13 | 174.59 (19) |
C4—C3—N4—N3 | −53.1 (2) | S1—C1—C2—C13 | −3.1 (3) |
C2—N1—N2—N3 | −0.9 (2) | O2—C13—C2—N1 | 174.9 (2) |
C1—N3—N2—N1 | −0.3 (2) | O1—C13—C2—N1 | −4.4 (3) |
N4—N3—N2—N1 | 175.74 (17) | O2—C13—C2—C1 | −0.9 (4) |
N2—N3—C1—C2 | 1.2 (2) | O1—C13—C2—C1 | 179.84 (19) |
N4—N3—C1—C2 | −174.19 (19) | C11—C6—C7—C8 | 1.3 (3) |
N2—N3—C1—S1 | 179.12 (14) | C5—C6—C7—C8 | −176.47 (17) |
N4—N3—C1—S1 | 3.7 (3) | C13—O1—C14—C15 | −170.7 (2) |
C4—S1—C1—N3 | 5.1 (2) | C9—C10—C11—C6 | −0.2 (3) |
C4—S1—C1—C2 | −177.6 (2) | C7—C6—C11—C10 | −1.1 (3) |
C3—C4—C5—O3 | 70.1 (2) | C5—C6—C11—C10 | 176.48 (17) |
S1—C4—C5—O3 | −55.1 (2) | C6—C7—C8—C9 | −0.1 (3) |
C3—C4—C5—C6 | −106.85 (18) | C10—C9—C8—C7 | −1.3 (3) |
S1—C4—C5—C6 | 127.92 (14) | C12—C9—C8—C7 | 178.18 (19) |
C14—O1—C13—O2 | −5.6 (3) |
C22H22N4O3S | F(000) = 1776 |
Mr = 422.49 | Dx = 1.379 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 25.4485 (8) Å | Cell parameters from 5356 reflections |
b = 8.9445 (3) Å | θ = 2.3–30.6° |
c = 19.0694 (7) Å | µ = 0.19 mm−1 |
β = 110.315 (4)° | T = 120 K |
V = 4070.7 (3) Å3 | Prism, colourless |
Z = 8 | 0.23 × 0.17 × 0.11 mm |
Xcalibur 3 diffractometer | 4741 reflections with I > 2σ(I) |
ω scans | Rint = 0.023 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | θmax = 30.6°, θmin = 2.3° |
Tmin = 0.910, Tmax = 1.000 | h = −34→35 |
11216 measured reflections | k = −11→12 |
5585 independent reflections | l = −25→23 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.035 | All H-atom parameters refined |
wR(F2) = 0.094 | w = 1/[σ2(Fo2) + (0.0477P)2 + 1.5461P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.034 |
5585 reflections | Δρmax = 0.36 e Å−3 |
359 parameters | Δρmin = −0.38 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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.65910 (2) | 0.94662 (3) | 0.44763 (2) | 0.01637 (8) | |
O1 | 0.69571 (3) | 1.23970 (10) | 0.52105 (5) | 0.02019 (18) | |
O3 | 0.52336 (3) | 0.90853 (11) | 0.33534 (5) | 0.02281 (19) | |
N4 | 0.60219 (4) | 0.94690 (11) | 0.26559 (5) | 0.0170 (2) | |
O2 | 0.66735 (4) | 1.46459 (10) | 0.46724 (5) | 0.0258 (2) | |
N1 | 0.63265 (4) | 1.31188 (11) | 0.32499 (6) | 0.0200 (2) | |
N3 | 0.62007 (4) | 1.07568 (11) | 0.30903 (5) | 0.01564 (19) | |
N2 | 0.61422 (4) | 1.20953 (11) | 0.27332 (6) | 0.0193 (2) | |
C1 | 0.64299 (4) | 1.09160 (13) | 0.38398 (6) | 0.0150 (2) | |
C4 | 0.61572 (4) | 0.80525 (13) | 0.38539 (6) | 0.0152 (2) | |
C5 | 0.55610 (4) | 0.83396 (13) | 0.38535 (6) | 0.0166 (2) | |
C17 | 0.71379 (5) | 0.66138 (14) | 0.35588 (7) | 0.0201 (2) | |
C6 | 0.54063 (4) | 0.78023 (13) | 0.44934 (6) | 0.0174 (2) | |
C19 | 0.58743 (5) | 0.68169 (14) | 0.25935 (7) | 0.0193 (2) | |
H19A | 0.5488 (6) | 0.6938 (16) | 0.2577 (8) | 0.024 (4)* | |
H19B | 0.5893 (7) | 0.6897 (19) | 0.2080 (9) | 0.036 (4)* | |
H19C | 0.6014 (6) | 0.5879 (18) | 0.2822 (8) | 0.027 (4)* | |
C22 | 0.71192 (5) | 0.87969 (14) | 0.28202 (7) | 0.0189 (2) | |
C16 | 0.68484 (4) | 0.78516 (13) | 0.31644 (6) | 0.0155 (2) | |
C13 | 0.67193 (5) | 1.33091 (14) | 0.46291 (7) | 0.0189 (2) | |
C18 | 0.76882 (5) | 0.63411 (15) | 0.36073 (7) | 0.0225 (3) | |
C21 | 0.76685 (5) | 0.85048 (14) | 0.28648 (7) | 0.0219 (2) | |
C2 | 0.65100 (4) | 1.24501 (13) | 0.39334 (6) | 0.0170 (2) | |
C3 | 0.62291 (4) | 0.80784 (13) | 0.30748 (6) | 0.0152 (2) | |
C9 | 0.50806 (5) | 0.69838 (15) | 0.57086 (7) | 0.0217 (2) | |
C10 | 0.47362 (5) | 0.78772 (16) | 0.51333 (7) | 0.0244 (3) | |
C8 | 0.55887 (5) | 0.65101 (16) | 0.56638 (7) | 0.0254 (3) | |
C15 | 0.66259 (5) | 1.31684 (17) | 0.62039 (8) | 0.0251 (3) | |
H15A | 0.6341 (6) | 1.3802 (18) | 0.5868 (9) | 0.029 (4)* | |
H15B | 0.6470 (7) | 1.2121 (19) | 0.6223 (9) | 0.033 (4)* | |
H15C | 0.6744 (6) | 1.3609 (18) | 0.6698 (9) | 0.033 (4)* | |
C11 | 0.48936 (5) | 0.82794 (15) | 0.45345 (7) | 0.0221 (2) | |
C14 | 0.71232 (5) | 1.30910 (16) | 0.59496 (7) | 0.0228 (3) | |
H14A | 0.7417 (6) | 1.2432 (16) | 0.6257 (8) | 0.018 (3)* | |
H14B | 0.7287 (6) | 1.4089 (17) | 0.5922 (8) | 0.026 (4)* | |
C20 | 0.79551 (5) | 0.72839 (15) | 0.32584 (7) | 0.0221 (3) | |
C12 | 0.49107 (6) | 0.6556 (2) | 0.63625 (8) | 0.0303 (3) | |
H12A | 0.4804 (8) | 0.747 (2) | 0.6592 (11) | 0.057 (6)* | |
H12B | 0.4588 (8) | 0.590 (2) | 0.6214 (11) | 0.055 (6)* | |
H12C | 0.5215 (8) | 0.610 (2) | 0.6735 (10) | 0.049 (5)* | |
C7 | 0.57527 (5) | 0.69069 (15) | 0.50668 (7) | 0.0235 (3) | |
H20 | 0.8325 (7) | 0.7082 (18) | 0.3283 (9) | 0.031 (4)* | |
H21 | 0.7849 (6) | 0.9175 (17) | 0.2593 (8) | 0.027 (4)* | |
H8 | 0.5832 (7) | 0.592 (2) | 0.6066 (10) | 0.041 (5)* | |
H11 | 0.4667 (6) | 0.8917 (17) | 0.4165 (8) | 0.025 (4)* | |
H4A | 0.6300 (5) | 0.7088 (15) | 0.4108 (7) | 0.014 (3)* | |
H22 | 0.6938 (6) | 0.9633 (16) | 0.2541 (8) | 0.020 (3)* | |
H7 | 0.6109 (6) | 0.6559 (18) | 0.5066 (9) | 0.031 (4)* | |
H4 | 0.5651 (7) | 0.9512 (18) | 0.2501 (9) | 0.032 (4)* | |
H18 | 0.7880 (6) | 0.5474 (18) | 0.3861 (9) | 0.029 (4)* | |
H10 | 0.4378 (7) | 0.8241 (19) | 0.5153 (9) | 0.040 (5)* | |
H17 | 0.6953 (6) | 0.5931 (17) | 0.3796 (8) | 0.023 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.01890 (13) | 0.01565 (14) | 0.01378 (13) | −0.00052 (10) | 0.00468 (10) | 0.00203 (10) |
O1 | 0.0230 (4) | 0.0194 (4) | 0.0191 (4) | −0.0002 (3) | 0.0085 (3) | −0.0016 (3) |
O3 | 0.0202 (4) | 0.0290 (5) | 0.0193 (4) | 0.0050 (3) | 0.0070 (3) | 0.0038 (4) |
N4 | 0.0184 (4) | 0.0163 (5) | 0.0154 (4) | 0.0004 (4) | 0.0048 (3) | 0.0006 (4) |
O2 | 0.0390 (5) | 0.0163 (4) | 0.0285 (5) | −0.0013 (4) | 0.0196 (4) | −0.0010 (4) |
N1 | 0.0241 (5) | 0.0173 (5) | 0.0229 (5) | 0.0033 (4) | 0.0135 (4) | 0.0033 (4) |
N3 | 0.0180 (4) | 0.0149 (5) | 0.0153 (4) | 0.0017 (3) | 0.0074 (3) | 0.0031 (4) |
N2 | 0.0229 (4) | 0.0169 (5) | 0.0207 (5) | 0.0041 (4) | 0.0109 (4) | 0.0056 (4) |
C1 | 0.0147 (4) | 0.0162 (5) | 0.0157 (5) | 0.0014 (4) | 0.0072 (4) | 0.0015 (4) |
C4 | 0.0160 (5) | 0.0151 (5) | 0.0156 (5) | 0.0004 (4) | 0.0068 (4) | 0.0009 (4) |
C5 | 0.0165 (5) | 0.0161 (5) | 0.0182 (5) | −0.0019 (4) | 0.0072 (4) | −0.0027 (4) |
C17 | 0.0219 (5) | 0.0221 (6) | 0.0184 (5) | 0.0016 (5) | 0.0098 (4) | 0.0025 (5) |
C6 | 0.0174 (5) | 0.0181 (6) | 0.0179 (5) | −0.0020 (4) | 0.0077 (4) | −0.0022 (4) |
C19 | 0.0192 (5) | 0.0193 (6) | 0.0201 (6) | −0.0018 (4) | 0.0076 (4) | −0.0029 (5) |
C22 | 0.0223 (5) | 0.0174 (6) | 0.0190 (5) | −0.0013 (4) | 0.0096 (4) | −0.0005 (5) |
C16 | 0.0170 (5) | 0.0163 (5) | 0.0141 (5) | −0.0010 (4) | 0.0066 (4) | −0.0022 (4) |
C13 | 0.0203 (5) | 0.0175 (6) | 0.0239 (6) | −0.0013 (4) | 0.0140 (4) | 0.0001 (5) |
C18 | 0.0220 (5) | 0.0278 (7) | 0.0176 (5) | 0.0062 (5) | 0.0069 (4) | 0.0013 (5) |
C21 | 0.0227 (5) | 0.0228 (6) | 0.0236 (6) | −0.0070 (5) | 0.0123 (5) | −0.0045 (5) |
C2 | 0.0182 (5) | 0.0154 (5) | 0.0208 (5) | 0.0020 (4) | 0.0110 (4) | 0.0020 (4) |
C3 | 0.0173 (5) | 0.0151 (5) | 0.0147 (5) | 0.0007 (4) | 0.0073 (4) | 0.0009 (4) |
C9 | 0.0197 (5) | 0.0267 (6) | 0.0211 (6) | −0.0040 (5) | 0.0098 (4) | −0.0008 (5) |
C10 | 0.0170 (5) | 0.0341 (7) | 0.0247 (6) | 0.0009 (5) | 0.0104 (4) | −0.0005 (5) |
C8 | 0.0240 (6) | 0.0304 (7) | 0.0248 (6) | 0.0054 (5) | 0.0121 (5) | 0.0081 (6) |
C15 | 0.0266 (6) | 0.0290 (7) | 0.0226 (6) | −0.0001 (5) | 0.0123 (5) | −0.0010 (5) |
C11 | 0.0179 (5) | 0.0278 (7) | 0.0208 (6) | 0.0023 (5) | 0.0069 (4) | 0.0014 (5) |
C14 | 0.0219 (5) | 0.0269 (7) | 0.0202 (6) | −0.0044 (5) | 0.0079 (4) | −0.0048 (5) |
C20 | 0.0166 (5) | 0.0310 (7) | 0.0193 (6) | −0.0015 (5) | 0.0069 (4) | −0.0072 (5) |
C12 | 0.0243 (6) | 0.0459 (9) | 0.0254 (7) | −0.0005 (6) | 0.0146 (5) | 0.0055 (6) |
C7 | 0.0206 (5) | 0.0281 (7) | 0.0257 (6) | 0.0058 (5) | 0.0130 (5) | 0.0054 (5) |
S1—C1 | 1.7255 (11) | C22—C21 | 1.3953 (16) |
S1—C4 | 1.8212 (11) | C22—H22 | 0.941 (14) |
O1—C13 | 1.3399 (15) | C16—C3 | 1.5386 (14) |
O1—C14 | 1.4618 (14) | C13—C2 | 1.4641 (17) |
O3—C5 | 1.2235 (14) | C18—C20 | 1.3887 (18) |
N4—N3 | 1.3994 (13) | C18—H18 | 0.954 (16) |
N4—C3 | 1.4734 (14) | C21—C20 | 1.3812 (18) |
N4—H4 | 0.886 (16) | C21—H21 | 1.002 (16) |
O2—C13 | 1.2069 (15) | C9—C10 | 1.3936 (18) |
N1—N2 | 1.3069 (14) | C9—C8 | 1.3914 (16) |
N1—C2 | 1.3608 (15) | C9—C12 | 1.5043 (18) |
N3—N2 | 1.3596 (13) | C10—C11 | 1.3826 (17) |
N3—C1 | 1.3507 (14) | C10—H10 | 0.980 (17) |
C1—C2 | 1.3896 (16) | C8—C7 | 1.3877 (17) |
C4—C5 | 1.5386 (15) | C8—H8 | 0.957 (17) |
C4—C3 | 1.5588 (15) | C15—H15A | 0.967 (16) |
C4—H4A | 0.995 (13) | C15—H15B | 1.022 (17) |
C5—C6 | 1.4860 (16) | C15—H15C | 0.968 (16) |
C17—C16 | 1.3963 (16) | C15—C14 | 1.5058 (17) |
C17—C18 | 1.3926 (16) | C11—H11 | 0.934 (15) |
C17—H17 | 0.972 (15) | C14—H14A | 0.972 (14) |
C6—C11 | 1.4005 (16) | C14—H14B | 0.994 (16) |
C6—C7 | 1.3946 (17) | C20—H20 | 0.944 (16) |
C19—H19A | 0.979 (15) | C12—H12A | 1.01 (2) |
C19—H19B | 0.999 (17) | C12—H12B | 0.97 (2) |
C19—H19C | 0.955 (16) | C12—H12C | 0.942 (19) |
C19—C3 | 1.5347 (16) | C7—H7 | 0.960 (16) |
C22—C16 | 1.3911 (16) | ||
C1—S1—C4 | 96.96 (5) | C20—C21—C22 | 120.66 (11) |
C13—O1—C14 | 115.82 (10) | C20—C21—H21 | 120.2 (9) |
N3—N4—C3 | 113.10 (8) | N1—C2—C1 | 108.95 (10) |
N3—N4—H4 | 104.6 (10) | N1—C2—C13 | 122.21 (11) |
C3—N4—H4 | 110.9 (10) | C1—C2—C13 | 128.72 (11) |
N2—N1—C2 | 109.15 (10) | N4—C3—C4 | 113.02 (9) |
N2—N3—N4 | 118.15 (9) | N4—C3—C19 | 105.72 (9) |
C1—N3—N4 | 130.19 (9) | N4—C3—C16 | 109.35 (9) |
C1—N3—N2 | 111.66 (9) | C19—C3—C4 | 108.65 (9) |
N1—N2—N3 | 106.92 (9) | C19—C3—C16 | 109.68 (9) |
N3—C1—S1 | 125.10 (9) | C16—C3—C4 | 110.29 (9) |
N3—C1—C2 | 103.30 (10) | C10—C9—C12 | 121.01 (11) |
C2—C1—S1 | 131.56 (9) | C8—C9—C10 | 118.04 (11) |
S1—C4—H4A | 104.4 (7) | C8—C9—C12 | 120.95 (12) |
C5—C4—S1 | 105.01 (7) | C9—C10—H10 | 119.9 (10) |
C5—C4—C3 | 116.05 (9) | C11—C10—C9 | 121.07 (11) |
C5—C4—H4A | 109.8 (7) | C11—C10—H10 | 119.0 (10) |
C3—C4—S1 | 111.45 (7) | C9—C8—H8 | 118.3 (10) |
C3—C4—H4A | 109.5 (8) | C7—C8—C9 | 121.54 (12) |
O3—C5—C4 | 119.73 (10) | C7—C8—H8 | 120.2 (10) |
O3—C5—C6 | 120.90 (10) | H15A—C15—H15B | 110.5 (13) |
C6—C5—C4 | 119.21 (9) | H15A—C15—H15C | 108.3 (13) |
C16—C17—H17 | 119.9 (8) | H15B—C15—H15C | 109.3 (13) |
C18—C17—C16 | 120.34 (11) | C14—C15—H15A | 109.5 (9) |
C18—C17—H17 | 119.8 (8) | C14—C15—H15B | 110.4 (9) |
C11—C6—C5 | 117.70 (10) | C14—C15—H15C | 108.7 (9) |
C7—C6—C5 | 123.64 (10) | C6—C11—H11 | 119.1 (9) |
C7—C6—C11 | 118.60 (11) | C10—C11—C6 | 120.63 (11) |
H19A—C19—H19B | 110.5 (13) | C10—C11—H11 | 120.2 (9) |
H19A—C19—H19C | 108.8 (12) | O1—C14—C15 | 109.63 (10) |
H19B—C19—H19C | 111.9 (13) | O1—C14—H14A | 103.2 (8) |
C3—C19—H19A | 108.2 (9) | O1—C14—H14B | 108.4 (9) |
C3—C19—H19B | 108.4 (10) | C15—C14—H14A | 112.9 (8) |
C3—C19—H19C | 108.9 (9) | C15—C14—H14B | 112.9 (9) |
C16—C22—C21 | 120.50 (11) | H14A—C14—H14B | 109.2 (12) |
C16—C22—H22 | 121.6 (9) | C18—C20—H20 | 120.4 (10) |
C21—C22—H22 | 117.9 (9) | C21—C20—C18 | 119.12 (11) |
C17—C16—C3 | 119.54 (10) | C21—C20—H20 | 120.5 (10) |
C22—C16—C17 | 118.73 (10) | C9—C12—H12A | 110.6 (11) |
C22—C16—C3 | 121.59 (10) | C9—C12—H12B | 111.7 (12) |
O1—C13—C2 | 110.36 (10) | C9—C12—H12C | 109.8 (11) |
O2—C13—O1 | 124.98 (11) | H12A—C12—H12B | 106.8 (16) |
O2—C13—C2 | 124.65 (12) | H12A—C12—H12C | 107.4 (15) |
C17—C18—H18 | 120.1 (9) | H12B—C12—H12C | 110.4 (16) |
C20—C18—C17 | 120.64 (12) | C6—C7—H7 | 121.7 (9) |
C20—C18—H18 | 119.2 (9) | C8—C7—C6 | 120.12 (11) |
C22—C21—H21 | 119.1 (9) | C8—C7—H7 | 118.2 (9) |
S1—C1—C2—N1 | 177.95 (8) | C5—C4—C3—C16 | 177.27 (9) |
S1—C1—C2—C13 | −5.80 (18) | C5—C6—C11—C10 | −176.99 (11) |
S1—C4—C5—O3 | 96.55 (11) | C5—C6—C7—C8 | 176.93 (12) |
S1—C4—C5—C6 | −78.82 (11) | C17—C16—C3—N4 | 178.71 (10) |
S1—C4—C3—N4 | −65.60 (10) | C17—C16—C3—C4 | 53.84 (13) |
S1—C4—C3—C19 | 177.40 (7) | C17—C16—C3—C19 | −65.78 (13) |
S1—C4—C3—C16 | 57.15 (11) | C17—C18—C20—C21 | 0.37 (18) |
O1—C13—C2—N1 | −169.89 (9) | C22—C16—C3—N4 | −5.59 (14) |
O1—C13—C2—C1 | 14.30 (16) | C22—C16—C3—C4 | −130.46 (11) |
O3—C5—C6—C11 | −5.06 (17) | C22—C16—C3—C19 | 109.92 (12) |
O3—C5—C6—C7 | 177.73 (12) | C22—C21—C20—C18 | 0.37 (18) |
N4—N3—N2—N1 | 178.89 (9) | C16—C17—C18—C20 | −0.71 (19) |
N4—N3—C1—S1 | 2.83 (16) | C16—C22—C21—C20 | −0.78 (18) |
N4—N3—C1—C2 | −179.27 (10) | C13—O1—C14—C15 | 83.47 (13) |
O2—C13—C2—N1 | 11.46 (17) | C18—C17—C16—C22 | 0.30 (17) |
O2—C13—C2—C1 | −164.35 (11) | C18—C17—C16—C3 | 176.12 (11) |
N3—N4—C3—C4 | 46.41 (12) | C21—C22—C16—C17 | 0.44 (17) |
N3—N4—C3—C19 | 165.13 (9) | C21—C22—C16—C3 | −175.29 (11) |
N3—N4—C3—C16 | −76.86 (11) | C2—N1—N2—N3 | 0.87 (11) |
N3—C1—C2—N1 | 0.25 (12) | C3—N4—N3—N2 | 165.77 (9) |
N3—C1—C2—C13 | 176.50 (10) | C3—N4—N3—C1 | −14.69 (15) |
N2—N1—C2—C1 | −0.71 (12) | C3—C4—C5—O3 | −26.98 (15) |
N2—N1—C2—C13 | −177.26 (10) | C3—C4—C5—C6 | 157.65 (10) |
N2—N3—C1—S1 | −177.61 (8) | C9—C10—C11—C6 | −0.3 (2) |
N2—N3—C1—C2 | 0.29 (12) | C9—C8—C7—C6 | 0.1 (2) |
C1—S1—C4—C5 | −80.97 (8) | C10—C9—C8—C7 | 0.0 (2) |
C1—S1—C4—C3 | 45.46 (8) | C8—C9—C10—C11 | 0.1 (2) |
C1—N3—N2—N1 | −0.73 (12) | C11—C6—C7—C8 | −0.25 (19) |
C4—S1—C1—N3 | −17.68 (10) | C14—O1—C13—O2 | 5.73 (16) |
C4—S1—C1—C2 | 165.05 (11) | C14—O1—C13—C2 | −172.92 (9) |
C4—C5—C6—C11 | 170.25 (11) | C12—C9—C10—C11 | 179.56 (13) |
C4—C5—C6—C7 | −6.95 (17) | C12—C9—C8—C7 | −179.46 (13) |
C5—C4—C3—N4 | 54.52 (13) | C7—C6—C11—C10 | 0.36 (19) |
C5—C4—C3—C19 | −62.49 (12) |
C21H20N4O4S | Z = 2 |
Mr = 424.47 | F(000) = 444 |
Triclinic, P1 | Dx = 1.386 Mg m−3 |
a = 9.2791 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.1445 (8) Å | Cell parameters from 2384 reflections |
c = 11.4872 (7) Å | θ = 2.3–29.0° |
α = 65.567 (7)° | µ = 0.20 mm−1 |
β = 73.829 (5)° | T = 295 K |
γ = 73.034 (6)° | Block, colourless |
V = 1017.32 (13) Å3 | 0.25 × 0.2 × 0.15 mm |
Xcalibur 3 diffractometer | 3602 reflections with I > 2σ(I) |
Detector resolution: 15.9555 pixels mm-1 | Rint = 0.027 |
ω scans | θmax = 30.9°, θmin = 2.3° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013) | h = −13→11 |
Tmin = 0.866, Tmax = 1.000 | k = −15→15 |
9054 measured reflections | l = −16→9 |
5427 independent reflections |
Refinement on F2 | Primary atom site location: iterative |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.049 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.134 | w = 1/[σ2(Fo2) + (0.062P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max = 0.001 |
5427 reflections | Δρmax = 0.30 e Å−3 |
310 parameters | Δρmin = −0.20 e Å−3 |
6 restraints |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1 | 0.01471 (5) | 0.17117 (5) | 0.95568 (5) | 0.04083 (15) | |
N4 | 0.26879 (16) | 0.29948 (16) | 0.98216 (17) | 0.0362 (3) | |
O3 | 0.29401 (19) | 0.34182 (16) | 0.71394 (15) | 0.0627 (4) | |
N1 | −0.07717 (18) | 0.39801 (16) | 1.16385 (15) | 0.0405 (4) | |
N2 | 0.07010 (17) | 0.39179 (16) | 1.12322 (15) | 0.0391 (4) | |
N3 | 0.11700 (15) | 0.31678 (14) | 1.04658 (14) | 0.0326 (3) | |
O4 | 0.3697 (2) | −0.22355 (18) | 1.47527 (16) | 0.0705 (5) | |
O2 | −0.31207 (14) | 0.22927 (16) | 1.10730 (16) | 0.0572 (4) | |
O1 | −0.38398 (15) | 0.40175 (16) | 1.17780 (15) | 0.0550 (4) | |
C1 | 0.00038 (18) | 0.27216 (17) | 1.04057 (17) | 0.0313 (4) | |
C21 | 0.4027 (2) | 0.0710 (2) | 1.1830 (2) | 0.0455 (5) | |
C4 | 0.22106 (19) | 0.14792 (19) | 0.88939 (18) | 0.0356 (4) | |
C2 | −0.12400 (19) | 0.32472 (18) | 1.11656 (17) | 0.0345 (4) | |
C17 | 0.2656 (2) | −0.0573 (2) | 1.1495 (2) | 0.0458 (5) | |
C18 | 0.2779 (2) | −0.1540 (2) | 1.2736 (2) | 0.0494 (5) | |
C19 | 0.3527 (2) | −0.1367 (2) | 1.3517 (2) | 0.0482 (5) | |
C5 | 0.2402 (2) | 0.2432 (2) | 0.7475 (2) | 0.0425 (4) | |
C20 | 0.4160 (2) | −0.0237 (2) | 1.3049 (2) | 0.0545 (6) | |
C13 | −0.2814 (2) | 0.3110 (2) | 1.13464 (19) | 0.0412 (4) | |
C7 | 0.1750 (3) | 0.0862 (3) | 0.6713 (2) | 0.0598 (6) | |
H7 | 0.195651 | 0.014749 | 0.747528 | 0.072* | |
C16 | 0.32559 (18) | 0.05698 (18) | 1.10229 (18) | 0.0353 (4) | |
C6 | 0.1867 (2) | 0.2137 (2) | 0.65276 (19) | 0.0450 (5) | |
C8 | 0.1321 (3) | 0.0645 (3) | 0.5753 (3) | 0.0780 (8) | |
H8 | 0.124491 | −0.021450 | 0.587646 | 0.094* | |
C3 | 0.31661 (19) | 0.16617 (18) | 0.96903 (19) | 0.0352 (4) | |
C11 | 0.1529 (3) | 0.3190 (3) | 0.5391 (2) | 0.0661 (6) | |
H11 | 0.159920 | 0.405455 | 0.525701 | 0.079* | |
C9 | 0.1016 (3) | 0.1689 (4) | 0.4639 (3) | 0.0795 (9) | |
H9 | 0.075501 | 0.153425 | 0.399577 | 0.095* | |
C12 | 0.3316 (3) | −0.3507 (3) | 1.5184 (3) | 0.0749 (7) | |
H12A | 0.391564 | −0.396838 | 1.460787 | 0.112* | |
H12B | 0.224700 | −0.338963 | 1.518982 | 0.112* | |
H12C | 0.352441 | −0.402616 | 1.604627 | 0.112* | |
C10 | 0.1088 (3) | 0.2965 (4) | 0.4456 (3) | 0.0823 (9) | |
H10 | 0.084155 | 0.367866 | 0.370521 | 0.099* | |
C15 | −0.6366 (3) | 0.5280 (3) | 1.2066 (3) | 0.0806 (8) | |
H15A | −0.622938 | 0.525189 | 1.287548 | 0.121* | 0.75 |
H15B | −0.743132 | 0.535243 | 1.209633 | 0.121* | 0.75 |
H15C | −0.601871 | 0.604452 | 1.137012 | 0.121* | 0.75 |
H15D | −0.603411 | 0.573668 | 1.246166 | 0.121* | 0.25 |
H15E | −0.742403 | 0.523453 | 1.241932 | 0.121* | 0.25 |
H15F | −0.624680 | 0.576346 | 1.114369 | 0.121* | 0.25 |
C14 | −0.5474 (7) | 0.4041 (6) | 1.1843 (4) | 0.0515 (11) | 0.75 |
H14A | −0.561651 | 0.404642 | 1.103602 | 0.062* | 0.75 |
H14B | −0.579485 | 0.325730 | 1.254974 | 0.062* | 0.75 |
H18 | 0.229 (3) | −0.226 (3) | 1.299 (2) | 0.067 (7)* | |
H17 | 0.215 (2) | −0.070 (2) | 1.099 (2) | 0.048 (6)* | |
H3 | 0.420 (2) | 0.1674 (19) | 0.9164 (18) | 0.037 (5)* | |
H20 | 0.465 (2) | −0.010 (2) | 1.361 (2) | 0.067 (7)* | |
H21 | 0.444 (2) | 0.143 (2) | 1.150 (2) | 0.051 (6)* | |
H4A | 0.2541 (18) | 0.056 (2) | 0.8909 (18) | 0.035 (5)* | |
H4 | 0.270 (2) | 0.367 (2) | 0.899 (2) | 0.062 (7)* | |
C22 | −0.537 (2) | 0.381 (2) | 1.2348 (15) | 0.061 (4) | 0.25 |
H22A | −0.546110 | 0.330789 | 1.327585 | 0.074* | 0.25 |
H22B | −0.567804 | 0.333378 | 1.194959 | 0.074* | 0.25 |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0377 (2) | 0.0408 (3) | 0.0562 (3) | −0.0079 (2) | −0.0093 (2) | −0.0287 (3) |
N4 | 0.0348 (7) | 0.0290 (8) | 0.0462 (10) | −0.0107 (6) | −0.0072 (7) | −0.0120 (8) |
O3 | 0.0942 (11) | 0.0457 (9) | 0.0495 (9) | −0.0308 (9) | −0.0124 (8) | −0.0077 (8) |
N1 | 0.0506 (9) | 0.0345 (9) | 0.0384 (9) | −0.0076 (7) | −0.0090 (7) | −0.0152 (8) |
N2 | 0.0511 (9) | 0.0328 (9) | 0.0398 (9) | −0.0080 (7) | −0.0138 (7) | −0.0161 (8) |
N3 | 0.0367 (7) | 0.0251 (8) | 0.0393 (8) | −0.0060 (6) | −0.0108 (6) | −0.0124 (7) |
O4 | 0.1018 (12) | 0.0549 (11) | 0.0487 (10) | −0.0126 (9) | −0.0251 (9) | −0.0075 (9) |
O2 | 0.0440 (7) | 0.0499 (9) | 0.0876 (12) | −0.0118 (7) | −0.0074 (7) | −0.0356 (9) |
O1 | 0.0428 (7) | 0.0515 (9) | 0.0736 (11) | −0.0070 (6) | 0.0015 (7) | −0.0349 (9) |
C1 | 0.0363 (8) | 0.0224 (8) | 0.0353 (9) | −0.0058 (7) | −0.0115 (7) | −0.0075 (8) |
C21 | 0.0489 (11) | 0.0369 (11) | 0.0548 (13) | −0.0095 (9) | −0.0176 (9) | −0.0147 (10) |
C4 | 0.0390 (9) | 0.0268 (9) | 0.0401 (10) | −0.0026 (7) | −0.0078 (7) | −0.0136 (9) |
C2 | 0.0421 (9) | 0.0256 (9) | 0.0347 (9) | −0.0069 (7) | −0.0071 (7) | −0.0097 (8) |
C17 | 0.0475 (10) | 0.0389 (11) | 0.0541 (13) | −0.0125 (9) | −0.0186 (9) | −0.0114 (10) |
C18 | 0.0538 (11) | 0.0365 (12) | 0.0538 (13) | −0.0152 (10) | −0.0124 (10) | −0.0065 (10) |
C19 | 0.0533 (11) | 0.0411 (12) | 0.0427 (12) | −0.0013 (9) | −0.0120 (9) | −0.0114 (10) |
C5 | 0.0483 (10) | 0.0330 (11) | 0.0435 (11) | −0.0059 (8) | −0.0071 (8) | −0.0136 (9) |
C20 | 0.0630 (13) | 0.0509 (14) | 0.0569 (14) | −0.0068 (11) | −0.0252 (11) | −0.0205 (12) |
C13 | 0.0431 (10) | 0.0340 (10) | 0.0419 (11) | −0.0056 (8) | −0.0053 (8) | −0.0121 (9) |
C7 | 0.0770 (15) | 0.0524 (14) | 0.0569 (14) | −0.0099 (12) | −0.0219 (12) | −0.0223 (13) |
C16 | 0.0302 (8) | 0.0308 (10) | 0.0438 (10) | −0.0034 (7) | −0.0080 (7) | −0.0135 (9) |
C6 | 0.0453 (10) | 0.0490 (13) | 0.0393 (11) | −0.0078 (9) | −0.0054 (8) | −0.0174 (10) |
C8 | 0.099 (2) | 0.081 (2) | 0.0758 (19) | −0.0243 (16) | −0.0233 (16) | −0.0410 (18) |
C3 | 0.0325 (8) | 0.0299 (10) | 0.0439 (10) | −0.0069 (7) | −0.0068 (7) | −0.0136 (9) |
C11 | 0.0834 (16) | 0.0640 (17) | 0.0479 (14) | −0.0252 (13) | −0.0188 (12) | −0.0060 (13) |
C9 | 0.0811 (17) | 0.122 (3) | 0.0545 (16) | −0.0370 (18) | −0.0122 (13) | −0.0398 (19) |
C12 | 0.100 (2) | 0.0496 (16) | 0.0548 (16) | −0.0078 (14) | −0.0187 (14) | −0.0014 (13) |
C10 | 0.0972 (19) | 0.108 (3) | 0.0421 (14) | −0.0416 (18) | −0.0225 (13) | −0.0068 (16) |
C15 | 0.0596 (14) | 0.074 (2) | 0.095 (2) | 0.0038 (13) | −0.0094 (14) | −0.0331 (18) |
C14 | 0.0417 (18) | 0.055 (3) | 0.056 (3) | −0.0119 (17) | −0.002 (2) | −0.021 (3) |
C22 | 0.045 (6) | 0.062 (8) | 0.076 (9) | −0.009 (5) | 0.004 (7) | −0.034 (7) |
S1—C1 | 1.7274 (16) | C5—C6 | 1.493 (3) |
S1—C4 | 1.8371 (17) | C20—H20 | 0.96 (2) |
N4—N3 | 1.3955 (19) | C7—H7 | 0.9300 |
N4—C3 | 1.480 (2) | C7—C6 | 1.380 (3) |
N4—H4 | 0.94 (2) | C7—C8 | 1.397 (3) |
O3—C5 | 1.212 (2) | C16—C3 | 1.517 (3) |
N1—N2 | 1.306 (2) | C6—C11 | 1.388 (3) |
N1—C2 | 1.363 (2) | C8—H8 | 0.9300 |
N2—N3 | 1.3587 (18) | C8—C9 | 1.360 (4) |
N3—C1 | 1.344 (2) | C3—H3 | 0.983 (18) |
O4—C19 | 1.369 (3) | C11—H11 | 0.9300 |
O4—C12 | 1.411 (3) | C11—C10 | 1.382 (3) |
O2—C13 | 1.203 (2) | C9—H9 | 0.9300 |
O1—C13 | 1.328 (2) | C9—C10 | 1.368 (4) |
O1—C14 | 1.491 (6) | C12—H12A | 0.9600 |
O1—C22 | 1.429 (19) | C12—H12B | 0.9600 |
C1—C2 | 1.380 (2) | C12—H12C | 0.9600 |
C21—C20 | 1.374 (3) | C10—H10 | 0.9300 |
C21—C16 | 1.396 (3) | C15—H15A | 0.9600 |
C21—H21 | 0.89 (2) | C15—H15B | 0.9600 |
C4—C5 | 1.528 (3) | C15—H15C | 0.9600 |
C4—C3 | 1.541 (2) | C15—H15D | 0.9600 |
C4—H4A | 0.974 (18) | C15—H15E | 0.9600 |
C2—C13 | 1.461 (2) | C15—H15F | 0.9600 |
C17—C18 | 1.398 (3) | C15—C14 | 1.471 (7) |
C17—C16 | 1.378 (3) | C15—C22 | 1.57 (2) |
C17—H17 | 0.916 (19) | C14—H14A | 0.9700 |
C18—C19 | 1.376 (3) | C14—H14B | 0.9700 |
C18—H18 | 0.93 (3) | C22—H22A | 0.9700 |
C19—C20 | 1.384 (3) | C22—H22B | 0.9700 |
C1—S1—C4 | 100.18 (8) | C7—C6—C5 | 122.9 (2) |
N3—N4—C3 | 109.92 (13) | C7—C6—C11 | 118.9 (2) |
N3—N4—H4 | 105.6 (13) | C11—C6—C5 | 118.1 (2) |
C3—N4—H4 | 109.3 (13) | C7—C8—H8 | 119.9 |
N2—N1—C2 | 108.93 (13) | C9—C8—C7 | 120.1 (3) |
N1—N2—N3 | 106.92 (12) | C9—C8—H8 | 119.9 |
N2—N3—N4 | 120.02 (13) | N4—C3—C4 | 113.34 (14) |
C1—N3—N4 | 128.47 (13) | N4—C3—C16 | 109.27 (14) |
C1—N3—N2 | 111.46 (13) | N4—C3—H3 | 103.5 (11) |
C19—O4—C12 | 117.90 (19) | C4—C3—H3 | 105.7 (10) |
C13—O1—C14 | 115.8 (3) | C16—C3—C4 | 114.90 (15) |
C13—O1—C22 | 119.9 (8) | C16—C3—H3 | 109.4 (11) |
N3—C1—S1 | 125.34 (12) | C6—C11—H11 | 119.7 |
N3—C1—C2 | 103.81 (14) | C10—C11—C6 | 120.6 (3) |
C2—C1—S1 | 130.85 (13) | C10—C11—H11 | 119.7 |
C20—C21—C16 | 121.6 (2) | C8—C9—H9 | 119.7 |
C20—C21—H21 | 122.3 (14) | C8—C9—C10 | 120.7 (2) |
C16—C21—H21 | 116.1 (14) | C10—C9—H9 | 119.7 |
S1—C4—H4A | 106.5 (10) | O4—C12—H12A | 109.5 |
C5—C4—S1 | 106.99 (12) | O4—C12—H12B | 109.5 |
C5—C4—C3 | 113.15 (16) | O4—C12—H12C | 109.5 |
C5—C4—H4A | 108.0 (11) | H12A—C12—H12B | 109.5 |
C3—C4—S1 | 113.58 (12) | H12A—C12—H12C | 109.5 |
C3—C4—H4A | 108.3 (10) | H12B—C12—H12C | 109.5 |
N1—C2—C1 | 108.86 (15) | C11—C10—H10 | 120.1 |
N1—C2—C13 | 126.13 (15) | C9—C10—C11 | 119.7 (3) |
C1—C2—C13 | 124.88 (16) | C9—C10—H10 | 120.1 |
C18—C17—H17 | 118.5 (14) | H15A—C15—H15B | 109.5 |
C16—C17—C18 | 121.92 (19) | H15A—C15—H15C | 109.5 |
C16—C17—H17 | 119.6 (14) | H15B—C15—H15C | 109.5 |
C17—C18—H18 | 116.0 (15) | H15D—C15—H15E | 109.5 |
C19—C18—C17 | 119.8 (2) | H15D—C15—H15F | 109.5 |
C19—C18—H18 | 124.1 (15) | H15E—C15—H15F | 109.5 |
O4—C19—C18 | 124.9 (2) | C14—C15—H15A | 109.5 |
O4—C19—C20 | 116.1 (2) | C14—C15—H15B | 109.5 |
C18—C19—C20 | 119.0 (2) | C14—C15—H15C | 109.5 |
O3—C5—C4 | 120.47 (17) | C22—C15—H15D | 109.5 |
O3—C5—C6 | 121.20 (19) | C22—C15—H15E | 109.5 |
C6—C5—C4 | 118.30 (17) | C22—C15—H15F | 109.5 |
C21—C20—C19 | 120.7 (2) | O1—C14—H14A | 110.5 |
C21—C20—H20 | 120.6 (15) | O1—C14—H14B | 110.5 |
C19—C20—H20 | 118.6 (15) | C15—C14—O1 | 106.3 (4) |
O2—C13—O1 | 124.75 (17) | C15—C14—H14A | 110.5 |
O2—C13—C2 | 122.45 (16) | C15—C14—H14B | 110.5 |
O1—C13—C2 | 112.73 (16) | H14A—C14—H14B | 108.7 |
C6—C7—H7 | 120.1 | O1—C22—C15 | 104.0 (12) |
C6—C7—C8 | 119.9 (2) | O1—C22—H22A | 111.0 |
C8—C7—H7 | 120.1 | O1—C22—H22B | 111.0 |
C21—C16—C3 | 118.08 (18) | C15—C22—H22A | 111.0 |
C17—C16—C21 | 117.03 (19) | C15—C22—H22B | 111.0 |
C17—C16—C3 | 124.87 (16) | H22A—C22—H22B | 109.0 |
S1—C1—C2—N1 | 179.63 (14) | C17—C18—C19—O4 | 179.02 (18) |
S1—C1—C2—C13 | −4.4 (3) | C17—C18—C19—C20 | −0.6 (3) |
S1—C4—C5—O3 | 108.89 (18) | C17—C16—C3—N4 | 133.70 (17) |
S1—C4—C5—C6 | −69.27 (17) | C17—C16—C3—C4 | 5.0 (2) |
S1—C4—C3—N4 | −57.59 (19) | C18—C17—C16—C21 | 1.4 (3) |
S1—C4—C3—C16 | 69.04 (17) | C18—C17—C16—C3 | −179.93 (18) |
N4—N3—C1—S1 | 4.1 (3) | C18—C19—C20—C21 | 0.9 (3) |
N4—N3—C1—C2 | −176.46 (17) | C5—C4—C3—N4 | 64.64 (19) |
O3—C5—C6—C7 | 157.0 (2) | C5—C4—C3—C16 | −168.73 (14) |
O3—C5—C6—C11 | −20.6 (3) | C5—C6—C11—C10 | 177.4 (2) |
N1—N2—N3—N4 | 176.01 (15) | C20—C21—C16—C17 | −1.1 (3) |
N1—N2—N3—C1 | −1.5 (2) | C20—C21—C16—C3 | −179.89 (17) |
N1—C2—C13—O2 | −168.5 (2) | C13—O1—C14—C15 | −168.1 (2) |
N1—C2—C13—O1 | 14.5 (3) | C13—O1—C22—C15 | −151.9 (5) |
N2—N1—C2—C1 | −1.1 (2) | C7—C6—C11—C10 | −0.3 (4) |
N2—N1—C2—C13 | −177.04 (17) | C7—C8—C9—C10 | −1.5 (4) |
N2—N3—C1—S1 | −178.70 (13) | C16—C21—C20—C19 | 0.0 (3) |
N2—N3—C1—C2 | 0.77 (19) | C16—C17—C18—C19 | −0.5 (3) |
N3—N4—C3—C4 | 61.1 (2) | C6—C7—C8—C9 | −0.2 (4) |
N3—N4—C3—C16 | −68.45 (17) | C6—C11—C10—C9 | −1.4 (4) |
N3—C1—C2—N1 | 0.2 (2) | C8—C7—C6—C5 | −176.5 (2) |
N3—C1—C2—C13 | 176.18 (18) | C8—C7—C6—C11 | 1.1 (3) |
O4—C19—C20—C21 | −178.78 (19) | C8—C9—C10—C11 | 2.3 (4) |
C1—S1—C4—C5 | −101.32 (13) | C3—N4—N3—N2 | 148.39 (15) |
C1—S1—C4—C3 | 24.26 (15) | C3—N4—N3—C1 | −34.6 (2) |
C1—C2—C13—O2 | 16.2 (3) | C3—C4—C5—O3 | −16.9 (2) |
C1—C2—C13—O1 | −160.81 (18) | C3—C4—C5—C6 | 164.89 (15) |
C21—C16—C3—N4 | −47.6 (2) | C12—O4—C19—C18 | 11.3 (3) |
C21—C16—C3—C4 | −176.32 (15) | C12—O4—C19—C20 | −169.0 (2) |
C4—S1—C1—N3 | 1.11 (18) | C14—O1—C13—O2 | −3.6 (4) |
C4—S1—C1—C2 | −178.20 (18) | C14—O1—C13—C2 | 173.3 (3) |
C4—C5—C6—C7 | −24.9 (3) | C22—O1—C13—O2 | 20.5 (8) |
C4—C5—C6—C11 | 157.56 (18) | C22—O1—C13—C2 | −162.5 (7) |
C2—N1—N2—N3 | 1.6 (2) |
`d_rmsp' is the distance from the atom to the r.m.s. plane of the thiadiazinane ring and RMSD is the r.m.s. deviation. |
Compound | Method | Ring-puckering parameters | Conformationa | d_rmsp (atom) (Å)b | ΔC2c | RMSD | ||
Q | Θ | φ | ||||||
(I) | X-ray | 0.486 | 47.7 | 84.0 | Half-Chair | 0.341 (C3), 0.292 (C4) | 13.55 | 0.00 |
OPLS3e | 0.513 | 45.5 | 87.0 | Half-Chair | 0.351 (C3), 0.317 C(4) | 12.01 | 0.61 | |
B3LYP 6-31G+** | 0.496 | 51.0 | 65.2 | Half-Chair/Enveloped | 0.363 (C3), 0.241 C(4) | 29.49 | 0.54 | |
(II) | X-ray | 0.493 | 46.4 | 84.0 | Half-Chair | 0.339 (C3), 0.305 (C4) | 15.05 | 0.00 |
OPLS3e | 0.514 | 45.8 | 87.3 | Half-Chair | 0.352 (C3), 0.318 (C4) | 11.75 | 0.46 | |
B3LYP 6-31G+** | 0.492 | 49.5 | 66.8 | Half-Chair/Enveloped | 0.359 (C3), 0.249 (C4) | 27.27 | 0.42 | |
(III) | X-ray | 0.499 | 49.3 | 93.3 | Half-Chair | 0.344 (C3), 0.308 (C4) | 10.37 | 0.00 |
OPLS3e | 0.519 | 46.5 | 98.7 | Half-Chair | 0.364 (C3), 0.306 (C4) | 16.67 | 0.40 | |
B3LYP 6-31G+** | 0.491 | 48.0 | 110.6 | Half-Chair/Enveloped | 0.356 (C3), 0.255 (C4) | 25.59 | 0.269 | |
(IV) | X-ray | 0.494 | 46.8 | 96.4 | Half-Chair | 0.345 (C3), 0.297 (C4) | 13.48 | 0.00 |
OPLS3e | 0.520 | 46.3 | 98.6 | Half-Chair | 0.363 (C3), 0.308 (C4) | 16.42 | 0.74 | |
B3LYP 6-31G+** | 0.492 | 48.2 | 111.7 | Half-Chair/Enveloped | 0.357 (C3), 0.252 (C4) | 26.46 | 0.66 | |
(V) | X-ray | 0.512 | 127.5 | 80.7 | Half-Chair | 0.363 (C3), 0.297 (C4) | 16.05 | 0.00 |
OPLS3e | 0.501 | 47.3 | 76.3 | Half-Chair | 0.356 (C3), 0.282 (C4) | 20.13 | 0.60 | |
B3LYP 6-31G+** | 0.487 | 47.4 | 72.3 | Half-Chair/Enveloped | 0.352 (C3), 0.262 (C4) | 23.04 | 1.12 | |
(VI) | X-ray | 0.526 | 47.4 | 78.6 | Half-Chair | 0.331 (C3), 0.353 (C4), | 2.21 | 0.00 |
OPLS3e | 0.543 | 46.8 | 82.2 | Half-Chair | 0.379 (C3), 0.324 (C4) | 16.17 | 0.69 | |
B3LYP 6-31G+** | 0.509 | 49.3 | 76.7 | Half-Chair | 0.365 (C3), 0.285 (C4) | 20.29 | 0.59 | |
(VII) | X-ray | 0.490 | 53.3 | 124.2 | Envelope | 0.357 (C3), 0.250 (N4) | 36.27 | 0.00 |
OPLS3e | 0.493 | 45.0 | 97.8 | Half-Chair | 0.318 (C3), 0.324 (C4) | 3.61 | 1.15 | |
B3LYP 6-31G+** | 0.505 | 56.6 | 56.0 | Envelope | 0.367 (C3), 0.255 (N4) | 38.51 | 0.62 |
Notes: (a) the distorted conformation is meant; (b) the atom numbering is according to the numbering in the displacement ellipsoid plots; (c) determined relative to the axis drawn through the bond centres corresponding to the C4—C3 and C1—N3 bonds in the isplacement ellipsoid plots; (d) it is quite difficult to expressly make attribution. |
`No' is the compound number and `Conf. N4' is the sum of the angles between the substituents of the N4 atom. |
O3—C5—N4—H4 | O3—C5—C4—C3 | C4—C3—N4—H4 | ||||
(I) | X-ray | 325 | 7.1 (2) | 25.5 (3) | 63.3 (3) | -0.0190 |
OPLS3e | 329 | 3.4 | 25.7 | 64.3 | -0.0203 | |
DFT | 328 | 2.4 | 28.2 | 58.7 | -0.0218 | |
(II) | X-ray | 326 | 6.9 (15) | 26.8 (3) | 63.3 (15) | -0.0168 |
OPLS3e | 329 | 2.3 | 24.2 | 64.5 | -0.0204 | |
DFT | 327 | 0.9 | 28.4 | 59.5 | -0.0219 | |
(III) | X-ray | 322 | 15.3 (14) | 33.4 (2) | 63.6 (13) | -0.0207 |
OPLS3e | 330 | 4.8 | 29.4 | 63.1 | -0.0210 | |
DFT | 329 | 5.9 | 32.8 | 60.6 | -0.0215 | |
(IV) | X-ray | 329 | 30 (2) | 56.5 (4) | 65 (2) | -0.0158 |
OPLS3e | 330 | 4.0 | 28.3 | 63.2 | -0.0210 | |
DFT | 328 | 6.2 | 34.6 | 59.8 | -0.0223 | |
(V) | X-ray | 327 | 39.7 (17) | 70.1 (2) | 61.8 (16) | -0.0124 |
OPLS3e | 330 | 27.2 | 57.5 | 62.3 | -0.0159 | |
DFT | 329 | 6.1 | 32.2 | 61.3 | -0.0215 | |
(VI) | X-ray | 330 | 17.1 (11) | 27.02 (15) | 71.5 (14) | -0.0117 |
OPLS3e | 329 | 4.5 | 27.9 | 60.0 | -0.0247 | |
DFT | 328 | 7.4 | 30.7 | 61.9 | -0.0227 | |
(VII) | X-ray | 325 | 19.2 (12) | 16.9 (2) | 54.4 (13) | -0.0175 |
OPLS3e | 329 | 3.7 | 23.0 | 69.9 | -0.0175 | |
DFT | 329 | 14.6 | 19.9 | 57.7 | -0.0205 |
Note: (a) a0 is the Bohr radius of 0.529 Å. |
Compounda | Method | S1···O (Å) | Interacting atoms | sign(λ2).ρ(r), e.a0-°3 a |
(I) | X-ray | 2.927 (2) | S1···O1 | –0.0134 |
OPLS3e | 3.11 | S1···O1 | -0.0095 | |
DFT | 2.97 | S1···O1 | -0.0122 | |
(II) | X-ray | 2.9278 (15) | S1···O1 | -0.0135 |
OPLS3e | 3.11 | S1···O1 | -0.0094 | |
DFT | 2.97 | S1···O1 | -0.0120 | |
(III) | X-ray | 2.8958 (13) | S1···O1 | -0.0141 |
OPLS3e | 2.87 | S1···O1 | -0.0093 | |
DFT | 2.97 | S1···O1 | -0.0121 | |
(IV) | X-ray | 2.970 (3) | S1···O1 | -0.0122 |
OPLS3e | 3.11 | S1···O1 | –0.0093 | |
DFT | 2.97 | S1···O1 | –0.0120 | |
(V) | X-ray | 3.1275 (17) | S1···O2 | -0.0095 |
OPLS3e | 3.28 | S1···O2 | – | |
DFT | 3.07 | S1···O2 | -0.0107 | |
(VI) | X-ray | 2.9652 (9) | S1···O1 | -0.0125 |
OPLS3e | 3.11 | S1···O1 | -0.0125 | |
DFT | 2.96 | S1···O1 | –0.0127 | |
(VII) | X-ray | 3.0810 (13) | S1···O2 | -0.0103 |
OPLS3e | 3.27 | S1···O2 | – | |
DFT | 3.07 | S1···O2 | -0.0107 |
Note: (a) a0 is the Bohr radius of 0.529 Å. |
Compound | Method | Contact | D—H (Å) | H···A (Å) | D—H···A (°) | D···A (Å) |
(I) | X-ray | N4—H4···O3 | 1.018 (2) | 2.188 (2) | 122.38 (16) | 2.865 (2) |
OPLS3e | N4—H4···O3 | 1.01 | 2.15 | 124.3 | 2.84 | |
DFT | N4—H4···O3 | 1.02 | 2.11 | 127.2 | 2.84 | |
X-ray | N4—H4···O3i | 1.018 (2) | 2.202 (2) | 149.94 (16) | 3.125 (2) | |
X-ray | C4—H4a···O2ii | 1.007 (3) | 2.449 (3) | 153.00 (19) | 3.378 (3) | |
(II) | X-ray | N4—H4···O3 | 0.87 (2) | 2.26 (2) | 123.4 (17) | 2.834 (2) |
OPLS3e | N4—H4···O3 | 1.01 | 2.15 | 124.2 | 2.84 | |
DFT | N4—H4···O3 | 1.02 | 2.11 | 126.8 | 2.84 | |
X-ray | N4—H4···O3iii | 0.87 (2) | 2.41 (2) | 152.6 (18) | 3.213 (2) | |
X-ray | C4—H4a···O2ii | 0.998 (19) | 2.442 (19) | 156.2 (16) | 3.379 (2) | |
(III) | X-ray | N4—H4···O3 | 0.879 (19) | 2.14 (2) | 128.8 (16) | 2.774 (2) |
OPLS3e | N4—H4···O3 | 1.01 | 2.12 | 125.2 | 2.84 | |
DFT | N4—H4···O3 | 1.02 | 2.12 | 126.1 | 2.84 | |
X-ray | C4—H4a···O2iv | 0.980 (2) | 2.458 (2) | 168.69 (17) | 3.425 (2) | |
X-ray | C10—H10···N2v | 0.930 (4) | 2.522 (3) | 166.8 (3) | 3.434 (3) | |
X-ray | C7—H7···O2iv | 0.930 (3) | 2.582 (2) | 139.1 (2) | 3.341 (3) | |
X-ray | C19—H19b···N1iv | 0.970 (3) | 2.599 (2) | 151.3 (2) | 3.480 (2) | |
(IV) | X-ray | N4—H4···O3 | 0.92 (3) | 2.29 (3) | 119 (3) | 2.848 (4) |
OPLS3e | N4—H4···O3 | 1.01 | 2.20 | 125.2 | 2.84 | |
DFT | N4—H4···O3 | 1.02 | 2.10 | 127.0 | 2.83 | |
X-ray | N4—H4···O4vi | 0.92 (3) | 2.51 (3) | 139 (3) | 3.264 (5) | |
(V) | X-ray | N4—H4···O3 | 0.82 (2) | 2.41 (2) | 121.3 (17) | 2.920 (3) |
OPLS3e | N4—H4···O3 | 1.01 | 2.27 | 121.3 | 2.93 | |
DFT | N4—H4···O3 | 1.02 | 2.12 | 125.5 | 2.84 | |
X-ray | N4—H4···O2vii | 0.82 (2) | 2.68 (2) | 124.9 (18) | 3.223 (2) | |
X-ray | C11—H11···N1viii | 0.930 (3) | 2.604 (3) | 165.28 (18) | 3.512 (3) | |
X-ray | C10—H10···O3viii | 0.930 (3) | 2.516 (2) | 168.8 (2) | 3.434 (2) | |
(VI) | X-ray | N4—H4···O3 | 0.890 (18) | 2.281 (18) | 115.9 (13) | 2.7868 (13) |
OPLS3e | N4—H4···O3 | 1.01 | 2.04 | 129.8 | 2.80 | |
DFT | N4—H4···O3 | 1.02 | 2.09 | 126.2 | 2.82 | |
X-ray | N4—H4···O3ix | 0.890 (18) | 2.299 (18) | 154.3 (15) | 3.1244 (13) | |
X-ray | C4—H4a···O2x | 1.014 (13) | 2.455 (13) | 177.4 (10) | 3.4682 (15) | |
X-ray | C7—H7···O2x | 0.961 (16) | 2.520 (16) | 147.9 (13) | 3.3722 (17) | |
X-ray | C17—H17···O2x | 0.990 (15) | 2.316 (15) | 163.9 (12) | 3.2779 (16) | |
(VII) | X-ray | N4—H4···O3 | 0.94 (2) | 2.20 (2) | 127.3 (18) | 2.869 (3) |
OPLS3e | N4—H4···O3 | 1.01 | 2.23 | 119.2 | 2.87 | |
DFT | N4—H4···O3 | 1.02 | 2.13 | 125.7 | 2.85 | |
X-ray | N4—H4···N1xi | 0.94 (2) | 2.646 (18) | 126.2 (15) | 3.290 (2) | |
X-ray | C21—H21···O2viii | 0.88 (2) | 2.56 (2) | 145.2 (18) | 3.324 (3) |
Symmetry codes: (i) -x, -y+1, -z; (ii) x-1, y, z; (iii) -x+1, -y+2, -z+1; (iv) x, y, z+1; (v) -x+2, y-1/2, -z+1; (vi) -x+1, -y+1, z-1/2; (vii) x, -y+1/2, z-1/2; (viii) x+1, y, z; (ix) -x+1, y, -z+1/2; (x) x, y-1, z; (xi) -x+1, -y+1, -z. |
Compound | IC50, µMa | |||
Hela | RDb | HEK293c | HFd | |
(I) | 0.11±0.07e | 33.63±4.52e | >10-4 | >10-4 |
(II) | 0.03±0.01e | >10-4 | >10-4 | >10-4 |
(III) | 3.23±0.38e | >10-4 | >10-4 | >10-4 |
(IV) | 2.05±0.08 | >10-4 | >10-4 | >10-4 |
(V) | 0.25±0.03e | 17.25±2.13e | 32.41±2.45e | >10-4 |
(VI) | >10-4 | >10-4 | >10-4 | >10-4 |
(VII) | 3.22±0.46 | >10-4 | >10-4 | >10-4 |
Camptothecin | 1.66±0.97 | 1.73±0.98 | 255.60±22.86 | 323.27±28.92 |
Notes: (a) IC50, compound concentration required to inhibit cell growth by 50% (mean ± SD, n = 4); (b) rhabdomyosarcoma tumour cell line; (c) human embryonic kidney cell line; (d) normal human fibroblast cell line; (e) p < 0.05 in comparison with the positive control (Mann–Whitney U test). |
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