Completing the picture of tolazamide polymorphism under extreme conditions: a low-temperature study
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619005217/ku3243sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229619005217/ku3243TZA_I_295sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229619005217/ku3243TZA_I_275sup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229619005217/ku3243TZA_I_250sup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229619005217/ku3243TZA_I_225sup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229619005217/ku3243TZA_I_200sup6.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229619005217/ku3243TZA_I_175sup7.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229619005217/ku3243TZA_I_150sup8.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229619005217/ku3243TZA_I_125sup9.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229619005217/ku3243TZA_I_100sup10.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229619005217/ku3243TZA_II_295sup11.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229619005217/ku3243TZA_II_250sup12.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229619005217/ku3243TZA_II_200sup13.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229619005217/ku3243TZA_II_150sup14.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229619005217/ku3243TZA_II_100sup15.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619005217/ku3243TZA_I_295sup16.cml | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2053229619005217/ku3243sup17.pdf |
CCDC references: 1910360; 1910359; 1910358; 1910357; 1910356; 1910355; 1910354; 1910353; 1910352; 1910351; 1910350; 1910349; 1910348; 1910347
Data collection: CrysAlis PRO (Rigaku OD, 2015) for TZA_I_295, TZA_II_295, TZA_II_250, TZA_II_200, TZA_II_150, TZA_II_100; CrysAlis PRO (Agilent, 2014) for TZA_I_275, TZA_I_250, TZA_I_225, TZA_I_200, TZA_I_175, TZA_I_150, TZA_I_125, TZA_I_100. Cell refinement: CrysAlis PRO (Rigaku OD, 2015) for TZA_I_295, TZA_II_295, TZA_II_250, TZA_II_200, TZA_II_150, TZA_II_100; CrysAlis PRO (Agilent, 2014) for TZA_I_275, TZA_I_250, TZA_I_225, TZA_I_200, TZA_I_175, TZA_I_150, TZA_I_125, TZA_I_100. Data reduction: CrysAlis PRO (Rigaku OD, 2015) for TZA_I_295, TZA_II_295, TZA_II_250, TZA_II_200, TZA_II_150, TZA_II_100; CrysAlis PRO (Agilent, 2014) for TZA_I_275, TZA_I_250, TZA_I_225, TZA_I_200, TZA_I_175, TZA_I_150, TZA_I_125, TZA_I_100. Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for TZA_I_295, TZA_II_295; SHELXT (Sheldrick, 2015a) for TZA_I_275, TZA_I_250, TZA_I_225, TZA_I_200, TZA_I_175, TZA_I_150, TZA_I_125, TZA_I_100, TZA_II_250, TZA_II_200, TZA_II_150, TZA_II_100. For all structures, program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009). Software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009) and PLATON (Spek, 2009) for TZA_I_295; OLEX2 (Dolomanov et al., 2009) for TZA_I_275, TZA_I_250, TZA_I_225, TZA_I_200, TZA_I_175, TZA_I_150, TZA_I_125, TZA_I_100, TZA_II_295, TZA_II_250, TZA_II_200, TZA_II_150, TZA_II_100.
C14H21N3O3S | F(000) = 332 |
Mr = 311.40 | Dx = 1.336 Mg m−3 |
Triclinic, P1 | Melting point: 444 K |
a = 6.3506 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.2241 (9) Å | Cell parameters from 3538 reflections |
c = 13.4984 (13) Å | θ = 2.3–24.0° |
α = 79.091 (8)° | µ = 0.22 mm−1 |
β = 87.215 (8)° | T = 295 K |
γ = 85.815 (8)° | Block, colourless |
V = 773.87 (13) Å3 | 0.4 × 0.1 × 0.05 mm |
Z = 2 |
Xcalibur, Ruby, Gemini ultra diffractometer | 3157 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2134 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.045 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 26.4°, θmin = 1.5° |
ω scans | h = −7→7 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | k = −11→11 |
Tmin = 0.912, Tmax = 1.000 | l = −16→16 |
12448 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.050 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.123 | w = 1/[σ2(Fo2) + (0.0469P)2 + 0.175P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
3157 reflections | Δρmax = 0.32 e Å−3 |
218 parameters | Δρmin = −0.26 e Å−3 |
2 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 | 0.02120 (10) | 0.27197 (6) | 0.22617 (5) | 0.0525 (2) | |
O1 | 0.1381 (3) | 0.15808 (18) | 0.18513 (13) | 0.0697 (5) | |
O2 | −0.2030 (3) | 0.27333 (19) | 0.23401 (14) | 0.0681 (5) | |
O3 | −0.0662 (3) | 0.45843 (17) | 0.38256 (12) | 0.0541 (4) | |
N1 | 0.1136 (4) | 0.2549 (2) | 0.33948 (15) | 0.0535 (5) | |
H1 | 0.210 (4) | 0.196 (3) | 0.3526 (19) | 0.052 (8)* | |
N2 | 0.1636 (4) | 0.3207 (2) | 0.49094 (16) | 0.0556 (6) | |
H2 | 0.137 (4) | 0.378 (3) | 0.5288 (19) | 0.055 (8)* | |
N3 | 0.3141 (3) | 0.2000 (2) | 0.51011 (14) | 0.0520 (5) | |
C1 | 0.2067 (4) | 0.7173 (3) | 0.05245 (18) | 0.0547 (6) | |
C2 | 0.3548 (4) | 0.6027 (3) | 0.0791 (2) | 0.0672 (7) | |
H2A | 0.4956 | 0.6170 | 0.0602 | 0.081* | |
C3 | 0.3020 (4) | 0.4662 (3) | 0.1333 (2) | 0.0633 (7) | |
H3 | 0.4057 | 0.3902 | 0.1506 | 0.076* | |
C4 | 0.0939 (4) | 0.4452 (2) | 0.16108 (16) | 0.0443 (5) | |
C5 | −0.0569 (4) | 0.5579 (3) | 0.1357 (2) | 0.0607 (7) | |
H5 | −0.1976 | 0.5441 | 0.1551 | 0.073* | |
C6 | 0.0003 (4) | 0.6929 (3) | 0.0807 (2) | 0.0640 (7) | |
H6 | −0.1036 | 0.7684 | 0.0627 | 0.077* | |
C7 | 0.2679 (5) | 0.8658 (3) | −0.0051 (2) | 0.0802 (9) | |
H7A | 0.4093 | 0.8564 | −0.0326 | 0.120* | |
H7B | 0.2606 | 0.9355 | 0.0397 | 0.120* | |
H7C | 0.1725 | 0.8999 | −0.0589 | 0.120* | |
C8 | 0.0612 (4) | 0.3526 (2) | 0.40410 (17) | 0.0457 (6) | |
C9 | 0.5260 (4) | 0.2532 (3) | 0.5135 (2) | 0.0666 (7) | |
H9AA | 0.6275 | 0.1712 | 0.5076 | 0.080* | 0.826 (6) |
H9AB | 0.5459 | 0.3284 | 0.4536 | 0.080* | 0.826 (6) |
H9BC | 0.5966 | 0.2522 | 0.4482 | 0.080* | 0.174 (6) |
H9BD | 0.5087 | 0.3555 | 0.5219 | 0.080* | 0.174 (6) |
C10A | 0.5835 (5) | 0.3148 (3) | 0.6004 (2) | 0.0624 (11) | 0.826 (6) |
H10A | 0.4717 | 0.3865 | 0.6141 | 0.075* | 0.826 (6) |
H10B | 0.7108 | 0.3673 | 0.5822 | 0.075* | 0.826 (6) |
C10B | 0.6665 (17) | 0.1744 (15) | 0.5905 (5) | 0.061 (5) | 0.174 (6) |
H10C | 0.8096 | 0.2005 | 0.5704 | 0.074* | 0.174 (6) |
H10D | 0.6616 | 0.0691 | 0.5918 | 0.074* | 0.174 (6) |
C11 | 0.6209 (5) | 0.2021 (4) | 0.6964 (2) | 0.0847 (9) | |
H11A | 0.7205 | 0.1248 | 0.6796 | 0.102* | 0.826 (6) |
H11B | 0.6897 | 0.2506 | 0.7426 | 0.102* | 0.826 (6) |
H11C | 0.7458 | 0.1696 | 0.7353 | 0.102* | 0.174 (6) |
H11D | 0.5975 | 0.3080 | 0.6931 | 0.102* | 0.174 (6) |
C12 | 0.4373 (4) | 0.1291 (4) | 0.7522 (2) | 0.0750 (8) | |
H12A | 0.4100 | 0.1702 | 0.8130 | 0.090* | |
H12B | 0.4793 | 0.0250 | 0.7734 | 0.090* | |
C13 | 0.2322 (4) | 0.1397 (3) | 0.69923 (19) | 0.0604 (7) | |
H13A | 0.1332 | 0.0795 | 0.7428 | 0.072* | |
H13B | 0.1743 | 0.2414 | 0.6896 | 0.068 (8)* | |
C14 | 0.2479 (5) | 0.0918 (3) | 0.5987 (2) | 0.0635 (7) | |
H14A | 0.352 (4) | 0.006 (3) | 0.608 (2) | 0.080 (9)* | |
H14B | 0.109 (4) | 0.062 (3) | 0.5863 (19) | 0.065 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0685 (4) | 0.0432 (3) | 0.0473 (4) | −0.0016 (3) | −0.0136 (3) | −0.0098 (3) |
O1 | 0.1059 (15) | 0.0490 (10) | 0.0580 (11) | 0.0109 (10) | −0.0181 (10) | −0.0219 (9) |
O2 | 0.0626 (11) | 0.0631 (11) | 0.0773 (13) | −0.0158 (9) | −0.0156 (9) | −0.0020 (10) |
O3 | 0.0624 (11) | 0.0487 (9) | 0.0485 (10) | 0.0116 (8) | −0.0043 (8) | −0.0071 (8) |
N1 | 0.0707 (15) | 0.0443 (12) | 0.0448 (12) | 0.0121 (11) | −0.0122 (10) | −0.0098 (10) |
N2 | 0.0750 (15) | 0.0491 (12) | 0.0427 (12) | 0.0135 (11) | −0.0097 (11) | −0.0129 (10) |
N3 | 0.0628 (13) | 0.0450 (11) | 0.0466 (12) | 0.0074 (10) | −0.0106 (10) | −0.0069 (9) |
C1 | 0.0659 (17) | 0.0583 (15) | 0.0410 (13) | −0.0107 (13) | −0.0091 (12) | −0.0076 (12) |
C2 | 0.0502 (15) | 0.0775 (19) | 0.0725 (19) | −0.0101 (14) | 0.0013 (13) | −0.0092 (16) |
C3 | 0.0507 (16) | 0.0614 (16) | 0.0745 (18) | 0.0110 (13) | −0.0073 (13) | −0.0082 (14) |
C4 | 0.0517 (14) | 0.0434 (12) | 0.0386 (12) | 0.0018 (11) | −0.0088 (10) | −0.0097 (10) |
C5 | 0.0482 (14) | 0.0607 (16) | 0.0663 (17) | 0.0026 (13) | −0.0041 (12) | 0.0035 (13) |
C6 | 0.0650 (18) | 0.0538 (15) | 0.0653 (17) | 0.0077 (13) | −0.0055 (14) | 0.0055 (13) |
C7 | 0.103 (2) | 0.0696 (19) | 0.0662 (19) | −0.0273 (18) | −0.0117 (17) | 0.0016 (15) |
C8 | 0.0556 (14) | 0.0407 (12) | 0.0391 (13) | −0.0061 (11) | 0.0017 (11) | −0.0030 (10) |
C9 | 0.0669 (18) | 0.0758 (18) | 0.0544 (16) | −0.0037 (15) | 0.0021 (13) | −0.0067 (14) |
C10A | 0.056 (2) | 0.060 (2) | 0.072 (2) | −0.0103 (16) | −0.0008 (16) | −0.0126 (17) |
C10B | 0.047 (9) | 0.081 (12) | 0.048 (9) | 0.015 (8) | 0.007 (7) | 0.000 (8) |
C11 | 0.0695 (19) | 0.119 (3) | 0.068 (2) | −0.0093 (19) | −0.0161 (16) | −0.0166 (19) |
C12 | 0.0702 (19) | 0.096 (2) | 0.0536 (17) | 0.0036 (16) | −0.0092 (14) | −0.0022 (16) |
C13 | 0.0629 (16) | 0.0559 (16) | 0.0569 (16) | −0.0083 (13) | 0.0042 (13) | 0.0034 (13) |
C14 | 0.078 (2) | 0.0474 (15) | 0.0642 (18) | −0.0132 (15) | −0.0135 (15) | −0.0028 (13) |
S1—O1 | 1.4241 (18) | C9—H9AA | 0.9700 |
S1—O2 | 1.4221 (18) | C9—H9AB | 0.9700 |
S1—N1 | 1.640 (2) | C9—H9BC | 0.9700 |
S1—C4 | 1.754 (2) | C9—H9BD | 0.9700 |
O3—C8 | 1.222 (3) | C9—C10A | 1.468 (4) |
N1—H1 | 0.79 (2) | C9—C10B | 1.454 (6) |
N1—C8 | 1.382 (3) | C10A—H10A | 0.9700 |
N2—H2 | 0.81 (2) | C10A—H10B | 0.9700 |
N2—N3 | 1.407 (3) | C10A—C11 | 1.517 (4) |
N2—C8 | 1.341 (3) | C10B—H10C | 0.9700 |
N3—C9 | 1.471 (3) | C10B—H10D | 0.9700 |
N3—C14 | 1.471 (3) | C10B—C11 | 1.511 (6) |
C1—C2 | 1.369 (4) | C11—H11A | 0.9700 |
C1—C6 | 1.370 (3) | C11—H11B | 0.9700 |
C1—C7 | 1.508 (4) | C11—H11C | 0.9700 |
C2—H2A | 0.9300 | C11—H11D | 0.9700 |
C2—C3 | 1.387 (4) | C11—C12 | 1.489 (4) |
C3—H3 | 0.9300 | C12—H12A | 0.9700 |
C3—C4 | 1.373 (3) | C12—H12B | 0.9700 |
C4—C5 | 1.367 (3) | C12—C13 | 1.505 (4) |
C5—H5 | 0.9300 | C13—H13A | 0.9700 |
C5—C6 | 1.386 (3) | C13—H13B | 0.9700 |
C6—H6 | 0.9300 | C13—C14 | 1.501 (4) |
C7—H7A | 0.9600 | C14—H14A | 0.99 (3) |
C7—H7B | 0.9600 | C14—H14B | 0.98 (3) |
C7—H7C | 0.9600 | ||
O1—S1—N1 | 103.56 (11) | C10A—C9—N3 | 120.1 (2) |
O1—S1—C4 | 109.54 (11) | C10A—C9—H9AA | 107.3 |
O2—S1—O1 | 119.57 (12) | C10A—C9—H9AB | 107.3 |
O2—S1—N1 | 109.05 (12) | C10B—C9—N3 | 118.3 (6) |
O2—S1—C4 | 108.78 (11) | C10B—C9—H9BC | 107.7 |
N1—S1—C4 | 105.38 (11) | C10B—C9—H9BD | 107.7 |
S1—N1—H1 | 116.1 (19) | C9—C10A—H10A | 108.5 |
C8—N1—S1 | 124.20 (19) | C9—C10A—H10B | 108.5 |
C8—N1—H1 | 118.6 (19) | C9—C10A—C11 | 115.1 (3) |
N3—N2—H2 | 123.5 (19) | H10A—C10A—H10B | 107.5 |
C8—N2—H2 | 115.1 (19) | C11—C10A—H10A | 108.5 |
C8—N2—N3 | 121.3 (2) | C11—C10A—H10B | 108.5 |
N2—N3—C9 | 110.09 (19) | C9—C10B—H10C | 108.2 |
N2—N3—C14 | 110.7 (2) | C9—C10B—H10D | 108.2 |
C14—N3—C9 | 115.6 (2) | C9—C10B—C11 | 116.3 (5) |
C2—C1—C6 | 117.6 (2) | H10C—C10B—H10D | 107.4 |
C2—C1—C7 | 121.5 (2) | C11—C10B—H10C | 108.2 |
C6—C1—C7 | 120.9 (3) | C11—C10B—H10D | 108.2 |
C1—C2—H2A | 118.9 | C10A—C11—H11A | 107.6 |
C1—C2—C3 | 122.3 (2) | C10A—C11—H11B | 107.6 |
C3—C2—H2A | 118.9 | C10B—C11—H11C | 108.2 |
C2—C3—H3 | 120.6 | C10B—C11—H11D | 108.2 |
C4—C3—C2 | 118.8 (2) | H11A—C11—H11B | 107.0 |
C4—C3—H3 | 120.6 | H11C—C11—H11D | 107.4 |
C3—C4—S1 | 119.85 (19) | C12—C11—C10A | 119.1 (3) |
C5—C4—S1 | 120.04 (18) | C12—C11—C10B | 116.3 (6) |
C5—C4—C3 | 120.1 (2) | C12—C11—H11A | 107.6 |
C4—C5—H5 | 120.1 | C12—C11—H11B | 107.6 |
C4—C5—C6 | 119.8 (2) | C12—C11—H11C | 108.2 |
C6—C5—H5 | 120.1 | C12—C11—H11D | 108.2 |
C1—C6—C5 | 121.4 (2) | C11—C12—H12A | 107.7 |
C1—C6—H6 | 119.3 | C11—C12—H12B | 107.7 |
C5—C6—H6 | 119.3 | C11—C12—C13 | 118.5 (2) |
C1—C7—H7A | 109.5 | H12A—C12—H12B | 107.1 |
C1—C7—H7B | 109.5 | C13—C12—H12A | 107.7 |
C1—C7—H7C | 109.5 | C13—C12—H12B | 107.7 |
H7A—C7—H7B | 109.5 | C12—C13—H13A | 108.5 |
H7A—C7—H7C | 109.5 | C12—C13—H13B | 108.5 |
H7B—C7—H7C | 109.5 | H13A—C13—H13B | 107.5 |
O3—C8—N1 | 122.2 (2) | C14—C13—C12 | 115.1 (2) |
O3—C8—N2 | 123.9 (2) | C14—C13—H13A | 108.5 |
N2—C8—N1 | 113.9 (2) | C14—C13—H13B | 108.5 |
N3—C9—H9AA | 107.3 | N3—C14—C13 | 117.8 (2) |
N3—C9—H9AB | 107.3 | N3—C14—H14A | 108.8 (16) |
N3—C9—H9BC | 107.7 | N3—C14—H14B | 107.8 (15) |
N3—C9—H9BD | 107.7 | C13—C14—H14A | 104.7 (17) |
H9AA—C9—H9AB | 106.9 | C13—C14—H14B | 107.1 (15) |
H9BC—C9—H9BD | 107.1 | H14A—C14—H14B | 111 (2) |
S1—N1—C8—O3 | 2.6 (3) | C2—C3—C4—S1 | 178.0 (2) |
S1—N1—C8—N2 | −176.90 (17) | C2—C3—C4—C5 | −0.3 (4) |
S1—C4—C5—C6 | −177.4 (2) | C3—C4—C5—C6 | 0.8 (4) |
O1—S1—N1—C8 | 173.1 (2) | C4—S1—N1—C8 | 58.1 (2) |
O1—S1—C4—C3 | −40.0 (2) | C4—C5—C6—C1 | −1.1 (4) |
O1—S1—C4—C5 | 138.3 (2) | C6—C1—C2—C3 | −0.4 (4) |
O2—S1—N1—C8 | −58.5 (2) | C7—C1—C2—C3 | 179.0 (2) |
O2—S1—C4—C3 | −172.3 (2) | C7—C1—C6—C5 | −178.5 (2) |
O2—S1—C4—C5 | 5.9 (2) | C8—N2—N3—C9 | 112.7 (2) |
N1—S1—C4—C3 | 70.9 (2) | C8—N2—N3—C14 | −118.3 (2) |
N1—S1—C4—C5 | −110.9 (2) | C9—N3—C14—C13 | 61.3 (3) |
N2—N3—C9—C10A | 73.1 (3) | C9—C10A—C11—C12 | −71.0 (4) |
N2—N3—C9—C10B | 139.2 (4) | C9—C10B—C11—C12 | 75.4 (11) |
N2—N3—C14—C13 | −64.7 (3) | C10A—C11—C12—C13 | 15.2 (4) |
N3—N2—C8—O3 | −177.8 (2) | C10B—C11—C12—C13 | −47.2 (5) |
N3—N2—C8—N1 | 1.7 (3) | C11—C12—C13—C14 | 53.0 (4) |
N3—C9—C10A—C11 | 73.3 (4) | C12—C13—C14—N3 | −82.9 (3) |
N3—C9—C10B—C11 | −76.0 (11) | C14—N3—C9—C10A | −53.2 (3) |
C1—C2—C3—C4 | 0.1 (4) | C14—N3—C9—C10B | 12.8 (5) |
C2—C1—C6—C5 | 1.0 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O3i | 0.81 (2) | 2.11 (3) | 2.912 (3) | 175 (2) |
Symmetry code: (i) −x, −y+1, −z+1. |
C14H21N3O3S | F(000) = 332 |
Mr = 311.40 | Dx = 1.343 Mg m−3 |
Triclinic, P1 | Melting point: 444 K |
a = 6.3453 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.1929 (5) Å | Cell parameters from 3671 reflections |
c = 13.4917 (7) Å | θ = 2.3–24.1° |
α = 79.103 (5)° | µ = 0.22 mm−1 |
β = 87.266 (4)° | T = 275 K |
γ = 85.857 (5)° | Block, colourless |
V = 770.32 (7) Å3 | 0.4 × 0.1 × 0.05 mm |
Z = 2 |
Xcalibur, Ruby, Gemini ultra diffractometer | 3149 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2245 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 26.4°, θmin = 2.3° |
ω scans | h = −7→7 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | k = −11→11 |
Tmin = 0.915, Tmax = 1.000 | l = −16→16 |
12387 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.048 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.115 | w = 1/[σ2(Fo2) + (0.0426P)2 + 0.2182P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
3149 reflections | Δρmax = 0.27 e Å−3 |
218 parameters | Δρmin = −0.21 e Å−3 |
2 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 | 0.02093 (10) | 0.27106 (6) | 0.22573 (4) | 0.0475 (2) | |
O1 | 0.1389 (3) | 0.15700 (18) | 0.18456 (12) | 0.0631 (5) | |
O2 | −0.2033 (3) | 0.27213 (19) | 0.23364 (13) | 0.0613 (5) | |
O3 | −0.0672 (2) | 0.45771 (17) | 0.38254 (11) | 0.0497 (4) | |
N1 | 0.1136 (4) | 0.2539 (2) | 0.33936 (14) | 0.0483 (5) | |
H1 | 0.209 (4) | 0.197 (3) | 0.3532 (18) | 0.045 (7)* | |
N2 | 0.1624 (3) | 0.3204 (2) | 0.49105 (15) | 0.0505 (5) | |
H2 | 0.135 (4) | 0.377 (3) | 0.5321 (19) | 0.059 (8)* | |
N3 | 0.3147 (3) | 0.2001 (2) | 0.51007 (13) | 0.0470 (5) | |
C1 | 0.2058 (4) | 0.7178 (3) | 0.05262 (16) | 0.0495 (6) | |
C2 | 0.3544 (4) | 0.6027 (3) | 0.0789 (2) | 0.0605 (7) | |
H2A | 0.4953 | 0.6171 | 0.0598 | 0.073* | |
C3 | 0.3020 (4) | 0.4660 (3) | 0.13291 (19) | 0.0571 (6) | |
H3 | 0.4058 | 0.3898 | 0.1501 | 0.068* | |
C4 | 0.0938 (3) | 0.4449 (2) | 0.16077 (15) | 0.0401 (5) | |
C5 | −0.0580 (4) | 0.5579 (3) | 0.13584 (18) | 0.0539 (6) | |
H5 | −0.1987 | 0.5437 | 0.1556 | 0.065* | |
C6 | −0.0013 (4) | 0.6932 (3) | 0.08114 (18) | 0.0570 (6) | |
H6 | −0.1054 | 0.7690 | 0.0633 | 0.068* | |
C7 | 0.2670 (5) | 0.8665 (3) | −0.0046 (2) | 0.0715 (8) | |
H7A | 0.4069 | 0.8566 | −0.0340 | 0.107* | |
H7B | 0.2643 | 0.9356 | 0.0407 | 0.107* | |
H7C | 0.1689 | 0.9023 | −0.0571 | 0.107* | |
C8 | 0.0616 (3) | 0.3523 (2) | 0.40436 (16) | 0.0413 (5) | |
C9 | 0.5267 (4) | 0.2536 (3) | 0.51312 (19) | 0.0614 (7) | |
H9AA | 0.5461 | 0.3290 | 0.4532 | 0.074* | 0.823 (6) |
H9AB | 0.6283 | 0.1715 | 0.5071 | 0.074* | 0.823 (6) |
H9BC | 0.5969 | 0.2528 | 0.4478 | 0.074* | 0.177 (6) |
H9BD | 0.5095 | 0.3563 | 0.5217 | 0.074* | 0.177 (6) |
C10A | 0.5847 (5) | 0.3160 (3) | 0.6003 (2) | 0.0560 (10) | 0.823 (6) |
H10A | 0.4727 | 0.3877 | 0.6143 | 0.067* | 0.823 (6) |
H10B | 0.7118 | 0.3690 | 0.5820 | 0.067* | 0.823 (6) |
C10B | 0.6676 (16) | 0.1740 (14) | 0.5903 (4) | 0.063 (5) | 0.177 (6) |
H10C | 0.8110 | 0.1997 | 0.5700 | 0.076* | 0.177 (6) |
H10D | 0.6618 | 0.0685 | 0.5916 | 0.076* | 0.177 (6) |
C11 | 0.6231 (4) | 0.2020 (4) | 0.6965 (2) | 0.0750 (8) | |
H11A | 0.7213 | 0.1240 | 0.6792 | 0.090* | 0.823 (6) |
H11B | 0.6937 | 0.2500 | 0.7426 | 0.090* | 0.823 (6) |
H11C | 0.7482 | 0.1687 | 0.7353 | 0.090* | 0.177 (6) |
H11D | 0.6010 | 0.3083 | 0.6932 | 0.090* | 0.177 (6) |
C12 | 0.4384 (4) | 0.1297 (3) | 0.75282 (19) | 0.0671 (7) | |
H12A | 0.4113 | 0.1717 | 0.8133 | 0.081* | |
H12B | 0.4797 | 0.0252 | 0.7746 | 0.081* | |
C13 | 0.2326 (4) | 0.1402 (3) | 0.69950 (18) | 0.0537 (6) | |
H13A | 0.1332 | 0.0801 | 0.7431 | 0.064* | |
H13B | 0.1750 | 0.2423 | 0.6894 | 0.068 (8)* | |
C14 | 0.2492 (5) | 0.0911 (3) | 0.5988 (2) | 0.0578 (7) | |
H14A | 0.352 (4) | 0.006 (3) | 0.6056 (19) | 0.068 (8)* | |
H14B | 0.115 (4) | 0.063 (3) | 0.5847 (18) | 0.064 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0617 (4) | 0.0393 (3) | 0.0426 (3) | −0.0013 (3) | −0.0118 (3) | −0.0088 (3) |
O1 | 0.0952 (13) | 0.0441 (10) | 0.0531 (10) | 0.0097 (9) | −0.0157 (9) | −0.0193 (8) |
O2 | 0.0571 (10) | 0.0563 (11) | 0.0694 (11) | −0.0149 (8) | −0.0139 (8) | −0.0018 (9) |
O3 | 0.0576 (10) | 0.0461 (10) | 0.0430 (9) | 0.0092 (8) | −0.0036 (7) | −0.0068 (7) |
N1 | 0.0652 (13) | 0.0387 (11) | 0.0404 (11) | 0.0097 (10) | −0.0130 (10) | −0.0080 (9) |
N2 | 0.0681 (13) | 0.0444 (12) | 0.0390 (11) | 0.0121 (10) | −0.0083 (9) | −0.0126 (9) |
N3 | 0.0563 (12) | 0.0408 (11) | 0.0423 (11) | 0.0068 (9) | −0.0081 (9) | −0.0062 (8) |
C1 | 0.0609 (15) | 0.0531 (15) | 0.0362 (12) | −0.0105 (12) | −0.0075 (11) | −0.0084 (11) |
C2 | 0.0443 (14) | 0.0713 (19) | 0.0650 (16) | −0.0115 (13) | 0.0024 (12) | −0.0088 (14) |
C3 | 0.0468 (14) | 0.0542 (16) | 0.0680 (17) | 0.0077 (12) | −0.0052 (12) | −0.0090 (13) |
C4 | 0.0453 (12) | 0.0415 (12) | 0.0339 (11) | 0.0016 (10) | −0.0066 (9) | −0.0088 (9) |
C5 | 0.0433 (13) | 0.0533 (15) | 0.0590 (15) | 0.0033 (11) | −0.0030 (11) | 0.0033 (12) |
C6 | 0.0570 (15) | 0.0462 (15) | 0.0607 (16) | 0.0094 (12) | −0.0055 (12) | 0.0040 (12) |
C7 | 0.091 (2) | 0.0610 (18) | 0.0608 (17) | −0.0212 (15) | −0.0116 (15) | 0.0025 (14) |
C8 | 0.0497 (13) | 0.0362 (12) | 0.0364 (12) | −0.0043 (10) | 0.0010 (10) | −0.0026 (10) |
C9 | 0.0626 (16) | 0.0694 (18) | 0.0494 (15) | −0.0041 (13) | 0.0006 (12) | −0.0051 (13) |
C10A | 0.0498 (17) | 0.054 (2) | 0.066 (2) | −0.0104 (15) | 0.0038 (14) | −0.0148 (16) |
C10B | 0.046 (8) | 0.088 (13) | 0.051 (9) | −0.009 (8) | 0.007 (7) | −0.001 (8) |
C11 | 0.0616 (17) | 0.107 (2) | 0.0581 (17) | −0.0091 (16) | −0.0131 (14) | −0.0149 (17) |
C12 | 0.0651 (17) | 0.084 (2) | 0.0473 (15) | 0.0035 (15) | −0.0063 (13) | −0.0026 (14) |
C13 | 0.0550 (14) | 0.0489 (15) | 0.0523 (15) | −0.0070 (11) | 0.0024 (11) | 0.0033 (11) |
C14 | 0.0723 (19) | 0.0414 (15) | 0.0593 (16) | −0.0095 (14) | −0.0142 (14) | −0.0026 (12) |
S1—O1 | 1.4268 (17) | C9—H9AA | 0.9700 |
S1—O2 | 1.4215 (17) | C9—H9AB | 0.9700 |
S1—N1 | 1.644 (2) | C9—H9BC | 0.9700 |
S1—C4 | 1.753 (2) | C9—H9BD | 0.9700 |
O3—C8 | 1.222 (3) | C9—C10A | 1.475 (4) |
N1—H1 | 0.78 (2) | C9—C10B | 1.458 (6) |
N1—C8 | 1.388 (3) | C10A—H10A | 0.9700 |
N2—H2 | 0.84 (3) | C10A—H10B | 0.9700 |
N2—N3 | 1.409 (3) | C10A—C11 | 1.524 (4) |
N2—C8 | 1.333 (3) | C10B—H10C | 0.9700 |
N3—C9 | 1.470 (3) | C10B—H10D | 0.9700 |
N3—C14 | 1.473 (3) | C10B—C11 | 1.514 (6) |
C1—C2 | 1.371 (4) | C11—H11A | 0.9700 |
C1—C6 | 1.374 (3) | C11—H11B | 0.9700 |
C1—C7 | 1.506 (3) | C11—H11C | 0.9700 |
C2—H2A | 0.9300 | C11—H11D | 0.9700 |
C2—C3 | 1.382 (3) | C11—C12 | 1.493 (4) |
C3—H3 | 0.9300 | C12—H12A | 0.9700 |
C3—C4 | 1.373 (3) | C12—H12B | 0.9700 |
C4—C5 | 1.369 (3) | C12—C13 | 1.509 (3) |
C5—H5 | 0.9300 | C13—H13A | 0.9700 |
C5—C6 | 1.384 (3) | C13—H13B | 0.9700 |
C6—H6 | 0.9300 | C13—C14 | 1.507 (4) |
C7—H7A | 0.9600 | C14—H14A | 0.98 (3) |
C7—H7B | 0.9600 | C14—H14B | 0.94 (3) |
C7—H7C | 0.9600 | ||
O1—S1—N1 | 103.49 (11) | H9BC—C9—H9BD | 107.2 |
O1—S1—C4 | 109.34 (10) | C10A—C9—H9AA | 107.3 |
O2—S1—O1 | 119.79 (11) | C10A—C9—H9AB | 107.3 |
O2—S1—N1 | 108.96 (11) | C10B—C9—N3 | 118.0 (6) |
O2—S1—C4 | 108.91 (10) | C10B—C9—H9BC | 107.8 |
N1—S1—C4 | 105.35 (10) | C10B—C9—H9BD | 107.8 |
S1—N1—H1 | 117.5 (18) | C9—C10A—H10A | 108.6 |
C8—N1—S1 | 124.33 (18) | C9—C10A—H10B | 108.6 |
C8—N1—H1 | 116.9 (18) | C9—C10A—C11 | 114.8 (2) |
N3—N2—H2 | 121.8 (18) | H10A—C10A—H10B | 107.6 |
C8—N2—H2 | 116.9 (18) | C11—C10A—H10A | 108.6 |
C8—N2—N3 | 121.21 (19) | C11—C10A—H10B | 108.6 |
N2—N3—C9 | 110.50 (18) | C9—C10B—H10C | 108.2 |
N2—N3—C14 | 110.53 (19) | C9—C10B—H10D | 108.2 |
C9—N3—C14 | 115.6 (2) | C9—C10B—C11 | 116.4 (5) |
C2—C1—C6 | 117.7 (2) | H10C—C10B—H10D | 107.3 |
C2—C1—C7 | 121.3 (2) | C11—C10B—H10C | 108.2 |
C6—C1—C7 | 121.0 (2) | C11—C10B—H10D | 108.2 |
C1—C2—H2A | 118.9 | C10A—C11—H11A | 107.6 |
C1—C2—C3 | 122.2 (2) | C10A—C11—H11B | 107.6 |
C3—C2—H2A | 118.9 | C10B—C11—H11C | 108.2 |
C2—C3—H3 | 120.6 | C10B—C11—H11D | 108.2 |
C4—C3—C2 | 118.8 (2) | H11A—C11—H11B | 107.0 |
C4—C3—H3 | 120.6 | H11C—C11—H11D | 107.3 |
C3—C4—S1 | 119.91 (18) | C12—C11—C10A | 118.8 (2) |
C5—C4—S1 | 119.75 (16) | C12—C11—C10B | 116.5 (6) |
C5—C4—C3 | 120.3 (2) | C12—C11—H11A | 107.6 |
C4—C5—H5 | 120.2 | C12—C11—H11B | 107.6 |
C4—C5—C6 | 119.7 (2) | C12—C11—H11C | 108.2 |
C6—C5—H5 | 120.2 | C12—C11—H11D | 108.2 |
C1—C6—C5 | 121.3 (2) | C11—C12—H12A | 107.7 |
C1—C6—H6 | 119.4 | C11—C12—H12B | 107.7 |
C5—C6—H6 | 119.4 | C11—C12—C13 | 118.4 (2) |
C1—C7—H7A | 109.5 | H12A—C12—H12B | 107.1 |
C1—C7—H7B | 109.5 | C13—C12—H12A | 107.7 |
C1—C7—H7C | 109.5 | C13—C12—H12B | 107.7 |
H7A—C7—H7B | 109.5 | C12—C13—H13A | 108.5 |
H7A—C7—H7C | 109.5 | C12—C13—H13B | 108.5 |
H7B—C7—H7C | 109.5 | H13A—C13—H13B | 107.5 |
O3—C8—N1 | 121.7 (2) | C14—C13—C12 | 114.9 (2) |
O3—C8—N2 | 124.1 (2) | C14—C13—H13A | 108.5 |
N2—C8—N1 | 114.2 (2) | C14—C13—H13B | 108.5 |
N3—C9—H9AA | 107.3 | N3—C14—C13 | 117.5 (2) |
N3—C9—H9AB | 107.3 | N3—C14—H14A | 107.8 (15) |
N3—C9—H9BC | 107.8 | N3—C14—H14B | 106.0 (16) |
N3—C9—H9BD | 107.8 | C13—C14—H14A | 106.7 (15) |
N3—C9—C10A | 120.0 (2) | C13—C14—H14B | 108.3 (15) |
H9AA—C9—H9AB | 106.9 | H14A—C14—H14B | 110 (2) |
S1—N1—C8—O3 | 3.3 (3) | C2—C3—C4—S1 | 177.93 (18) |
S1—N1—C8—N2 | −177.16 (16) | C2—C3—C4—C5 | −0.4 (3) |
S1—C4—C5—C6 | −177.48 (18) | C3—C4—C5—C6 | 0.9 (3) |
O1—S1—N1—C8 | 172.74 (19) | C4—S1—N1—C8 | 58.0 (2) |
O1—S1—C4—C3 | −39.6 (2) | C4—C5—C6—C1 | −1.2 (4) |
O1—S1—C4—C5 | 138.71 (19) | C6—C1—C2—C3 | −0.5 (4) |
O2—S1—N1—C8 | −58.8 (2) | C7—C1—C2—C3 | 178.9 (2) |
O2—S1—C4—C3 | −172.24 (18) | C7—C1—C6—C5 | −178.5 (2) |
O2—S1—C4—C5 | 6.1 (2) | C8—N2—N3—C9 | 111.9 (2) |
N1—S1—C4—C3 | 71.0 (2) | C8—N2—N3—C14 | −118.9 (2) |
N1—S1—C4—C5 | −110.6 (2) | C9—N3—C14—C13 | 61.9 (3) |
N2—N3—C9—C10A | 73.1 (3) | C9—C10A—C11—C12 | −71.8 (3) |
N2—N3—C9—C10B | 139.2 (4) | C9—C10B—C11—C12 | 75.2 (11) |
N2—N3—C14—C13 | −64.6 (3) | C10A—C11—C12—C13 | 16.1 (4) |
N3—N2—C8—O3 | −177.74 (19) | C10B—C11—C12—C13 | −46.6 (5) |
N3—N2—C8—N1 | 2.7 (3) | C11—C12—C13—C14 | 52.8 (3) |
N3—C9—C10A—C11 | 73.4 (3) | C12—C13—C14—N3 | −83.4 (3) |
N3—C9—C10B—C11 | −76.3 (11) | C14—N3—C9—C10A | −53.4 (3) |
C1—C2—C3—C4 | 0.2 (4) | C14—N3—C9—C10B | 12.8 (4) |
C2—C1—C6—C5 | 1.0 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O3i | 0.84 (3) | 2.08 (3) | 2.911 (3) | 172 (2) |
Symmetry code: (i) −x, −y+1, −z+1. |
C14H21N3O3S | F(000) = 332 |
Mr = 311.40 | Dx = 1.351 Mg m−3 |
Triclinic, P1 | Melting point: 444 K |
a = 6.3346 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.1641 (5) Å | Cell parameters from 4017 reflections |
c = 13.4642 (7) Å | θ = 2.3–26.5° |
α = 79.222 (4)° | µ = 0.23 mm−1 |
β = 87.305 (4)° | T = 250 K |
γ = 85.936 (4)° | Block, colourless |
V = 765.43 (7) Å3 | 0.4 × 0.1 × 0.05 mm |
Z = 2 |
Xcalibur, Ruby, Gemini ultra diffractometer | 3131 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2355 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 26.4°, θmin = 2.3° |
ω scans | h = −7→7 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | k = −11→11 |
Tmin = 0.919, Tmax = 1.000 | l = −16→16 |
12313 measured reflections |
Refinement on F2 | 2 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) = 0.111 | w = 1/[σ2(Fo2) + (0.0434P)2 + 0.1936P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
3131 reflections | Δρmax = 0.30 e Å−3 |
218 parameters | Δρmin = −0.22 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 | 0.02087 (9) | 0.27000 (6) | 0.22520 (4) | 0.04136 (18) | |
O1 | 0.1394 (3) | 0.15591 (17) | 0.18364 (11) | 0.0553 (4) | |
O2 | −0.2039 (2) | 0.27037 (17) | 0.23306 (12) | 0.0539 (4) | |
O3 | −0.0680 (2) | 0.45699 (16) | 0.38256 (10) | 0.0432 (4) | |
N1 | 0.1140 (3) | 0.2527 (2) | 0.33923 (13) | 0.0429 (5) | |
H1 | 0.208 (4) | 0.196 (3) | 0.3532 (18) | 0.048 (7)* | |
N2 | 0.1619 (3) | 0.3197 (2) | 0.49126 (14) | 0.0450 (5) | |
H2 | 0.138 (3) | 0.380 (3) | 0.5300 (17) | 0.049 (7)* | |
N3 | 0.3157 (3) | 0.19975 (19) | 0.51009 (13) | 0.0426 (4) | |
C1 | 0.2052 (3) | 0.7188 (2) | 0.05231 (15) | 0.0424 (5) | |
C2 | 0.3545 (4) | 0.6032 (3) | 0.07873 (18) | 0.0516 (6) | |
H2A | 0.4956 | 0.6180 | 0.0599 | 0.062* | |
C3 | 0.3022 (3) | 0.4660 (3) | 0.13218 (17) | 0.0496 (6) | |
H3 | 0.4061 | 0.3894 | 0.1487 | 0.060* | |
C4 | 0.0934 (3) | 0.4446 (2) | 0.16062 (14) | 0.0353 (5) | |
C5 | −0.0600 (3) | 0.5578 (3) | 0.13592 (17) | 0.0470 (5) | |
H5 | −0.2007 | 0.5432 | 0.1557 | 0.056* | |
C6 | −0.0030 (4) | 0.6937 (3) | 0.08124 (17) | 0.0498 (6) | |
H6 | −0.1073 | 0.7697 | 0.0637 | 0.060* | |
C7 | 0.2667 (4) | 0.8675 (3) | −0.00456 (19) | 0.0625 (7) | |
H7A | 0.4063 | 0.8573 | −0.0345 | 0.094* | |
H7B | 0.2654 | 0.9364 | 0.0412 | 0.094* | |
H7C | 0.1678 | 0.9039 | −0.0567 | 0.094* | |
C8 | 0.0609 (3) | 0.3512 (2) | 0.40422 (14) | 0.0369 (5) | |
C9 | 0.5277 (4) | 0.2545 (3) | 0.51281 (17) | 0.0537 (6) | |
H9AA | 0.5460 | 0.3308 | 0.4531 | 0.064* | 0.834 (6) |
H9AB | 0.6302 | 0.1728 | 0.5061 | 0.064* | 0.834 (6) |
H9BC | 0.5976 | 0.2555 | 0.4470 | 0.064* | 0.166 (6) |
H9BD | 0.5108 | 0.3567 | 0.5231 | 0.064* | 0.166 (6) |
C10A | 0.5858 (4) | 0.3166 (3) | 0.6007 (2) | 0.0488 (9) | 0.834 (6) |
H10A | 0.4727 | 0.3872 | 0.6156 | 0.059* | 0.834 (6) |
H10B | 0.7122 | 0.3709 | 0.5825 | 0.059* | 0.834 (6) |
C10B | 0.6675 (16) | 0.1709 (14) | 0.5897 (4) | 0.056 (5) | 0.166 (6) |
H10C | 0.8123 | 0.1928 | 0.5690 | 0.067* | 0.166 (6) |
H10D | 0.6553 | 0.0656 | 0.5913 | 0.067* | 0.166 (6) |
C11 | 0.6267 (4) | 0.2009 (3) | 0.69647 (18) | 0.0629 (7) | |
H11A | 0.7223 | 0.1221 | 0.6780 | 0.075* | 0.834 (6) |
H11B | 0.7008 | 0.2478 | 0.7423 | 0.075* | 0.834 (6) |
H11C | 0.7524 | 0.1668 | 0.7348 | 0.075* | 0.166 (6) |
H11D | 0.6069 | 0.3077 | 0.6928 | 0.075* | 0.166 (6) |
C12 | 0.4405 (4) | 0.1301 (3) | 0.75386 (18) | 0.0573 (6) | |
H12A | 0.4138 | 0.1741 | 0.8137 | 0.069* | |
H12B | 0.4807 | 0.0255 | 0.7767 | 0.069* | |
C13 | 0.2340 (3) | 0.1404 (3) | 0.69991 (16) | 0.0460 (5) | |
H13A | 0.1339 | 0.0806 | 0.7435 | 0.055* | |
H13B | 0.1766 | 0.2429 | 0.6895 | 0.050 (6)* | |
C14 | 0.2517 (5) | 0.0903 (3) | 0.59926 (18) | 0.0511 (6) | |
H14A | 0.357 (4) | 0.003 (3) | 0.6037 (17) | 0.058 (7)* | |
H14B | 0.121 (4) | 0.061 (3) | 0.5850 (17) | 0.054 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0533 (3) | 0.0342 (3) | 0.0374 (3) | −0.0007 (2) | −0.0102 (2) | −0.0073 (2) |
O1 | 0.0819 (11) | 0.0393 (9) | 0.0477 (9) | 0.0081 (8) | −0.0126 (8) | −0.0175 (7) |
O2 | 0.0507 (9) | 0.0498 (10) | 0.0604 (10) | −0.0131 (7) | −0.0115 (7) | −0.0021 (8) |
O3 | 0.0509 (9) | 0.0387 (9) | 0.0383 (8) | 0.0079 (7) | −0.0039 (6) | −0.0059 (7) |
N1 | 0.0561 (12) | 0.0368 (11) | 0.0353 (10) | 0.0080 (9) | −0.0099 (9) | −0.0070 (8) |
N2 | 0.0611 (12) | 0.0389 (11) | 0.0354 (10) | 0.0113 (9) | −0.0082 (9) | −0.0120 (9) |
N3 | 0.0526 (11) | 0.0368 (10) | 0.0375 (10) | 0.0052 (8) | −0.0082 (8) | −0.0060 (8) |
C1 | 0.0522 (13) | 0.0448 (13) | 0.0316 (11) | −0.0082 (11) | −0.0059 (9) | −0.0078 (9) |
C2 | 0.0394 (12) | 0.0616 (16) | 0.0538 (14) | −0.0090 (11) | 0.0026 (10) | −0.0094 (12) |
C3 | 0.0399 (12) | 0.0478 (14) | 0.0588 (14) | 0.0073 (10) | −0.0046 (10) | −0.0067 (11) |
C4 | 0.0412 (11) | 0.0361 (11) | 0.0289 (10) | 0.0021 (9) | −0.0068 (8) | −0.0073 (8) |
C5 | 0.0374 (11) | 0.0472 (14) | 0.0505 (13) | 0.0014 (10) | −0.0021 (10) | 0.0050 (11) |
C6 | 0.0503 (13) | 0.0412 (13) | 0.0522 (14) | 0.0068 (10) | −0.0056 (11) | 0.0032 (11) |
C7 | 0.0765 (17) | 0.0551 (16) | 0.0546 (15) | −0.0193 (13) | −0.0095 (13) | 0.0003 (12) |
C8 | 0.0455 (12) | 0.0327 (11) | 0.0315 (11) | −0.0050 (9) | 0.0025 (9) | −0.0032 (9) |
C9 | 0.0547 (14) | 0.0592 (15) | 0.0446 (13) | −0.0024 (12) | −0.0002 (11) | −0.0035 (11) |
C10A | 0.0448 (15) | 0.0454 (18) | 0.0573 (18) | −0.0085 (13) | 0.0024 (13) | −0.0115 (13) |
C10B | 0.036 (8) | 0.082 (12) | 0.042 (8) | −0.003 (7) | 0.001 (6) | 0.005 (7) |
C11 | 0.0522 (14) | 0.087 (2) | 0.0510 (15) | −0.0072 (13) | −0.0098 (11) | −0.0147 (14) |
C12 | 0.0561 (14) | 0.0677 (17) | 0.0439 (14) | 0.0052 (12) | −0.0061 (11) | −0.0020 (12) |
C13 | 0.0481 (12) | 0.0421 (13) | 0.0436 (13) | −0.0053 (10) | 0.0024 (10) | 0.0029 (10) |
C14 | 0.0640 (16) | 0.0383 (14) | 0.0508 (14) | −0.0103 (12) | −0.0135 (12) | −0.0018 (11) |
S1—O1 | 1.4275 (16) | C9—H9AA | 0.9700 |
S1—O2 | 1.4229 (16) | C9—H9AB | 0.9700 |
S1—N1 | 1.6465 (19) | C9—H9BC | 0.9700 |
S1—C4 | 1.753 (2) | C9—H9BD | 0.9700 |
O3—C8 | 1.223 (2) | C9—C10A | 1.477 (3) |
N1—H1 | 0.77 (2) | C9—C10B | 1.462 (6) |
N1—C8 | 1.385 (3) | C10A—H10A | 0.9700 |
N2—H2 | 0.83 (2) | C10A—H10B | 0.9700 |
N2—N3 | 1.411 (2) | C10A—C11 | 1.528 (4) |
N2—C8 | 1.336 (3) | C10B—H10C | 0.9700 |
N3—C9 | 1.471 (3) | C10B—H10D | 0.9700 |
N3—C14 | 1.475 (3) | C10B—C11 | 1.520 (6) |
C1—C2 | 1.375 (3) | C11—H11A | 0.9700 |
C1—C6 | 1.380 (3) | C11—H11B | 0.9700 |
C1—C7 | 1.501 (3) | C11—H11C | 0.9700 |
C2—H2A | 0.9300 | C11—H11D | 0.9700 |
C2—C3 | 1.381 (3) | C11—C12 | 1.498 (3) |
C3—H3 | 0.9300 | C12—H12A | 0.9700 |
C3—C4 | 1.377 (3) | C12—H12B | 0.9700 |
C4—C5 | 1.374 (3) | C12—C13 | 1.515 (3) |
C5—H5 | 0.9300 | C13—H13A | 0.9700 |
C5—C6 | 1.386 (3) | C13—H13B | 0.9700 |
C6—H6 | 0.9300 | C13—C14 | 1.507 (3) |
C7—H7A | 0.9600 | C14—H14A | 1.00 (3) |
C7—H7B | 0.9600 | C14—H14B | 0.92 (2) |
C7—H7C | 0.9600 | ||
O1—S1—N1 | 103.47 (10) | H9BC—C9—H9BD | 107.3 |
O1—S1—C4 | 109.39 (10) | C10A—C9—H9AA | 107.4 |
O2—S1—O1 | 119.69 (10) | C10A—C9—H9AB | 107.4 |
O2—S1—N1 | 109.02 (10) | C10B—C9—N3 | 116.5 (6) |
O2—S1—C4 | 108.96 (10) | C10B—C9—H9BC | 108.2 |
N1—S1—C4 | 105.31 (9) | C10B—C9—H9BD | 108.2 |
S1—N1—H1 | 117.8 (18) | C9—C10A—H10A | 108.6 |
C8—N1—S1 | 124.03 (17) | C9—C10A—H10B | 108.6 |
C8—N1—H1 | 117.0 (18) | C9—C10A—C11 | 114.6 (2) |
N3—N2—H2 | 122.6 (16) | H10A—C10A—H10B | 107.6 |
C8—N2—H2 | 115.9 (16) | C11—C10A—H10A | 108.6 |
C8—N2—N3 | 121.16 (18) | C11—C10A—H10B | 108.6 |
N2—N3—C9 | 110.60 (17) | C9—C10B—H10C | 108.3 |
N2—N3—C14 | 110.56 (18) | C9—C10B—H10D | 108.3 |
C9—N3—C14 | 115.49 (18) | C9—C10B—C11 | 116.0 (4) |
C2—C1—C6 | 117.6 (2) | H10C—C10B—H10D | 107.4 |
C2—C1—C7 | 121.2 (2) | C11—C10B—H10C | 108.3 |
C6—C1—C7 | 121.2 (2) | C11—C10B—H10D | 108.3 |
C1—C2—H2A | 118.8 | C10A—C11—H11A | 107.7 |
C1—C2—C3 | 122.3 (2) | C10A—C11—H11B | 107.7 |
C3—C2—H2A | 118.8 | C10B—C11—H11C | 108.3 |
C2—C3—H3 | 120.6 | C10B—C11—H11D | 108.3 |
C4—C3—C2 | 118.8 (2) | H11A—C11—H11B | 107.1 |
C4—C3—H3 | 120.6 | H11C—C11—H11D | 107.4 |
C3—C4—S1 | 119.86 (16) | C12—C11—C10A | 118.2 (2) |
C5—C4—S1 | 119.60 (15) | C12—C11—C10B | 116.1 (6) |
C5—C4—C3 | 120.5 (2) | C12—C11—H11A | 107.7 |
C4—C5—H5 | 120.3 | C12—C11—H11B | 107.7 |
C4—C5—C6 | 119.39 (19) | C12—C11—H11C | 108.3 |
C6—C5—H5 | 120.3 | C12—C11—H11D | 108.3 |
C1—C6—C5 | 121.4 (2) | C11—C12—H12A | 107.8 |
C1—C6—H6 | 119.3 | C11—C12—H12B | 107.8 |
C5—C6—H6 | 119.3 | C11—C12—C13 | 118.1 (2) |
C1—C7—H7A | 109.5 | H12A—C12—H12B | 107.1 |
C1—C7—H7B | 109.5 | C13—C12—H12A | 107.8 |
C1—C7—H7C | 109.5 | C13—C12—H12B | 107.8 |
H7A—C7—H7B | 109.5 | C12—C13—H13A | 108.6 |
H7A—C7—H7C | 109.5 | C12—C13—H13B | 108.6 |
H7B—C7—H7C | 109.5 | H13A—C13—H13B | 107.6 |
O3—C8—N1 | 122.08 (19) | C14—C13—C12 | 114.7 (2) |
O3—C8—N2 | 123.79 (19) | C14—C13—H13A | 108.6 |
N2—C8—N1 | 114.12 (19) | C14—C13—H13B | 108.6 |
N3—C9—H9AA | 107.4 | N3—C14—C13 | 117.40 (19) |
N3—C9—H9AB | 107.4 | N3—C14—H14A | 106.7 (13) |
N3—C9—H9BC | 108.2 | N3—C14—H14B | 105.7 (15) |
N3—C9—H9BD | 108.2 | C13—C14—H14A | 108.9 (14) |
N3—C9—C10A | 119.82 (19) | C13—C14—H14B | 108.8 (14) |
H9AA—C9—H9AB | 106.9 | H14A—C14—H14B | 109 (2) |
S1—N1—C8—O3 | 3.0 (3) | C2—C3—C4—S1 | 178.07 (17) |
S1—N1—C8—N2 | −177.16 (15) | C2—C3—C4—C5 | 0.2 (3) |
S1—C4—C5—C6 | −177.36 (17) | C3—C4—C5—C6 | 0.5 (3) |
O1—S1—N1—C8 | 172.84 (17) | C4—S1—N1—C8 | 58.0 (2) |
O1—S1—C4—C3 | −39.22 (19) | C4—C5—C6—C1 | −1.0 (3) |
O1—S1—C4—C5 | 138.67 (17) | C6—C1—C2—C3 | 0.0 (3) |
O2—S1—N1—C8 | −58.76 (19) | C7—C1—C2—C3 | 179.1 (2) |
O2—S1—C4—C3 | −171.75 (16) | C7—C1—C6—C5 | −178.4 (2) |
O2—S1—C4—C5 | 6.1 (2) | C8—N2—N3—C9 | 111.5 (2) |
N1—S1—C4—C3 | 71.41 (19) | C8—N2—N3—C14 | −119.3 (2) |
N1—S1—C4—C5 | −110.70 (18) | C9—N3—C14—C13 | 62.4 (3) |
N2—N3—C9—C10A | 73.6 (3) | C9—C10A—C11—C12 | −73.5 (3) |
N2—N3—C9—C10B | 140.4 (4) | C9—C10B—C11—C12 | 76.7 (10) |
N2—N3—C14—C13 | −64.2 (3) | C10A—C11—C12—C13 | 17.9 (4) |
N3—N2—C8—O3 | −177.22 (18) | C10B—C11—C12—C13 | −45.7 (4) |
N3—N2—C8—N1 | 3.0 (3) | C11—C12—C13—C14 | 52.0 (3) |
N3—C9—C10A—C11 | 73.7 (3) | C12—C13—C14—N3 | −84.2 (3) |
N3—C9—C10B—C11 | −78.8 (10) | C14—N3—C9—C10A | −52.9 (3) |
C1—C2—C3—C4 | −0.5 (3) | C14—N3—C9—C10B | 13.9 (4) |
C2—C1—C6—C5 | 0.7 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O3i | 0.83 (2) | 2.08 (2) | 2.909 (2) | 175 (2) |
Symmetry code: (i) −x, −y+1, −z+1. |
C14H21N3O3S | F(000) = 332 |
Mr = 311.40 | Dx = 1.360 Mg m−3 |
Triclinic, P1 | Melting point: 444 K |
a = 6.3186 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.1502 (8) Å | Cell parameters from 4337 reflections |
c = 13.4244 (11) Å | θ = 2.3–27.4° |
α = 79.314 (7)° | µ = 0.23 mm−1 |
β = 87.303 (7)° | T = 225 K |
γ = 85.948 (7)° | Block, colourless |
V = 760.32 (11) Å3 | 0.4 × 0.1 × 0.05 mm |
Z = 2 |
Xcalibur, Ruby, Gemini ultra diffractometer | 3111 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2425 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 26.4°, θmin = 2.3° |
ω scans | h = −7→7 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | k = −11→11 |
Tmin = 0.926, Tmax = 1.000 | l = −16→16 |
12225 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.044 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.100 | w = 1/[σ2(Fo2) + (0.035P)2 + 0.266P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
3111 reflections | Δρmax = 0.27 e Å−3 |
218 parameters | Δρmin = −0.29 e Å−3 |
2 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 | 0.02064 (8) | 0.26910 (5) | 0.22470 (4) | 0.03595 (16) | |
O1 | 0.1400 (2) | 0.15506 (16) | 0.18281 (11) | 0.0477 (4) | |
O2 | −0.2046 (2) | 0.26908 (16) | 0.23244 (11) | 0.0468 (4) | |
O3 | −0.0693 (2) | 0.45636 (15) | 0.38274 (10) | 0.0384 (3) | |
N1 | 0.1134 (3) | 0.2518 (2) | 0.33898 (13) | 0.0371 (4) | |
H1 | 0.211 (3) | 0.197 (3) | 0.3521 (17) | 0.041 (7)* | |
N2 | 0.1619 (3) | 0.3191 (2) | 0.49142 (13) | 0.0403 (4) | |
H2 | 0.141 (3) | 0.378 (2) | 0.5305 (16) | 0.039 (6)* | |
N3 | 0.3167 (3) | 0.19950 (18) | 0.50980 (12) | 0.0376 (4) | |
C1 | 0.2042 (3) | 0.7193 (2) | 0.05232 (14) | 0.0366 (5) | |
C2 | 0.3547 (3) | 0.6034 (3) | 0.07830 (17) | 0.0454 (5) | |
H2A | 0.4961 | 0.6183 | 0.0592 | 0.055* | |
C3 | 0.3022 (3) | 0.4659 (2) | 0.13183 (16) | 0.0430 (5) | |
H3 | 0.4064 | 0.3894 | 0.1484 | 0.052* | |
C4 | 0.0927 (3) | 0.4443 (2) | 0.16025 (14) | 0.0309 (4) | |
C5 | −0.0612 (3) | 0.5579 (2) | 0.13603 (16) | 0.0405 (5) | |
H5 | −0.2021 | 0.5431 | 0.1562 | 0.049* | |
C6 | −0.0052 (3) | 0.6942 (2) | 0.08150 (16) | 0.0438 (5) | |
H6 | −0.1099 | 0.7702 | 0.0642 | 0.053* | |
C7 | 0.2654 (4) | 0.8690 (3) | −0.00424 (18) | 0.0535 (6) | |
H7A | 0.4035 | 0.8587 | −0.0362 | 0.080* | |
H7B | 0.2683 | 0.9367 | 0.0423 | 0.080* | |
H7C | 0.1635 | 0.9071 | −0.0550 | 0.080* | |
C8 | 0.0604 (3) | 0.3506 (2) | 0.40424 (14) | 0.0318 (4) | |
C9 | 0.5286 (3) | 0.2557 (3) | 0.51235 (16) | 0.0474 (5) | |
H9AA | 0.5454 | 0.3329 | 0.4529 | 0.057* | 0.838 (5) |
H9AB | 0.6322 | 0.1748 | 0.5048 | 0.057* | 0.838 (5) |
H9BC | 0.5984 | 0.2575 | 0.4463 | 0.057* | 0.162 (5) |
H9BD | 0.5107 | 0.3578 | 0.5232 | 0.057* | 0.162 (5) |
C10A | 0.5872 (4) | 0.3173 (3) | 0.60146 (19) | 0.0431 (8) | 0.838 (5) |
H10A | 0.4734 | 0.3871 | 0.6172 | 0.052* | 0.838 (5) |
H10B | 0.7133 | 0.3724 | 0.5834 | 0.052* | 0.838 (5) |
C10B | 0.6699 (16) | 0.1716 (14) | 0.5894 (4) | 0.053 (5) | 0.162 (5) |
H10C | 0.8149 | 0.1941 | 0.5686 | 0.064* | 0.162 (5) |
H10D | 0.6584 | 0.0662 | 0.5904 | 0.064* | 0.162 (5) |
C11 | 0.6298 (4) | 0.2002 (3) | 0.69633 (17) | 0.0537 (6) | |
H11A | 0.7234 | 0.1210 | 0.6766 | 0.064* | 0.838 (5) |
H11B | 0.7067 | 0.2458 | 0.7422 | 0.064* | 0.838 (5) |
H11C | 0.7559 | 0.1651 | 0.7345 | 0.064* | 0.162 (5) |
H11D | 0.6115 | 0.3071 | 0.6932 | 0.064* | 0.162 (5) |
C12 | 0.4417 (3) | 0.1300 (3) | 0.75479 (16) | 0.0494 (6) | |
H12A | 0.4154 | 0.1750 | 0.8145 | 0.059* | |
H12B | 0.4812 | 0.0253 | 0.7781 | 0.059* | |
C13 | 0.2353 (3) | 0.1408 (2) | 0.70054 (15) | 0.0405 (5) | |
H13A | 0.1786 | 0.2436 | 0.6897 | 0.049* | |
H13B | 0.1343 | 0.0815 | 0.7442 | 0.050 (6)* | |
C14 | 0.2540 (4) | 0.0894 (3) | 0.59933 (17) | 0.0455 (5) | |
H14A | 0.359 (4) | 0.004 (3) | 0.6023 (17) | 0.058 (7)* | |
H14B | 0.120 (4) | 0.059 (2) | 0.5849 (16) | 0.047 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0461 (3) | 0.0299 (3) | 0.0325 (3) | −0.0010 (2) | −0.0089 (2) | −0.0061 (2) |
O1 | 0.0707 (10) | 0.0336 (8) | 0.0411 (9) | 0.0074 (7) | −0.0109 (7) | −0.0146 (7) |
O2 | 0.0445 (8) | 0.0437 (9) | 0.0517 (9) | −0.0103 (7) | −0.0102 (7) | −0.0023 (7) |
O3 | 0.0447 (8) | 0.0350 (8) | 0.0341 (8) | 0.0062 (7) | −0.0026 (6) | −0.0054 (6) |
N1 | 0.0480 (11) | 0.0318 (10) | 0.0307 (9) | 0.0076 (8) | −0.0087 (8) | −0.0059 (7) |
N2 | 0.0552 (11) | 0.0343 (10) | 0.0319 (10) | 0.0106 (8) | −0.0086 (8) | −0.0107 (8) |
N3 | 0.0455 (10) | 0.0333 (9) | 0.0329 (9) | 0.0053 (8) | −0.0084 (7) | −0.0048 (7) |
C1 | 0.0451 (12) | 0.0396 (12) | 0.0265 (10) | −0.0072 (10) | −0.0052 (9) | −0.0069 (9) |
C2 | 0.0332 (11) | 0.0538 (14) | 0.0490 (13) | −0.0068 (10) | 0.0014 (9) | −0.0077 (11) |
C3 | 0.0364 (11) | 0.0410 (13) | 0.0496 (13) | 0.0071 (9) | −0.0048 (9) | −0.0059 (10) |
C4 | 0.0362 (10) | 0.0307 (10) | 0.0261 (9) | 0.0008 (8) | −0.0042 (8) | −0.0068 (8) |
C5 | 0.0322 (10) | 0.0399 (12) | 0.0449 (12) | 0.0025 (9) | −0.0009 (9) | 0.0025 (10) |
C6 | 0.0425 (12) | 0.0381 (12) | 0.0456 (13) | 0.0076 (10) | −0.0042 (10) | 0.0025 (10) |
C7 | 0.0641 (15) | 0.0484 (14) | 0.0470 (14) | −0.0156 (12) | −0.0085 (11) | 0.0001 (11) |
C8 | 0.0378 (11) | 0.0283 (10) | 0.0285 (10) | −0.0052 (9) | 0.0023 (8) | −0.0030 (8) |
C9 | 0.0494 (13) | 0.0515 (14) | 0.0389 (12) | −0.0016 (11) | −0.0014 (10) | −0.0025 (10) |
C10A | 0.0383 (14) | 0.0412 (16) | 0.0514 (17) | −0.0083 (11) | 0.0035 (12) | −0.0112 (12) |
C10B | 0.033 (7) | 0.072 (11) | 0.049 (9) | 0.000 (7) | 0.003 (6) | 0.004 (8) |
C11 | 0.0442 (13) | 0.0742 (17) | 0.0439 (13) | −0.0045 (12) | −0.0104 (10) | −0.0118 (12) |
C12 | 0.0490 (13) | 0.0605 (15) | 0.0354 (12) | 0.0039 (11) | −0.0045 (10) | −0.0018 (11) |
C13 | 0.0417 (11) | 0.0388 (12) | 0.0372 (11) | −0.0054 (9) | 0.0016 (9) | 0.0035 (9) |
C14 | 0.0561 (15) | 0.0336 (12) | 0.0472 (13) | −0.0075 (11) | −0.0116 (11) | −0.0040 (10) |
S1—O1 | 1.4283 (15) | C9—H9AA | 0.9700 |
S1—O2 | 1.4218 (15) | C9—H9AB | 0.9700 |
S1—N1 | 1.6442 (18) | C9—H9BC | 0.9700 |
S1—C4 | 1.7542 (19) | C9—H9BD | 0.9700 |
O3—C8 | 1.224 (2) | C9—C10A | 1.486 (3) |
N1—H1 | 0.77 (2) | C9—C10B | 1.467 (6) |
N1—C8 | 1.386 (3) | C10A—H10A | 0.9700 |
N2—H2 | 0.82 (2) | C10A—H10B | 0.9700 |
N2—N3 | 1.409 (2) | C10A—C11 | 1.526 (3) |
N2—C8 | 1.335 (3) | C10B—H10C | 0.9700 |
N3—C9 | 1.472 (3) | C10B—H10D | 0.9700 |
N3—C14 | 1.476 (3) | C10B—C11 | 1.513 (6) |
C1—C2 | 1.379 (3) | C11—H11A | 0.9700 |
C1—C6 | 1.385 (3) | C11—H11B | 0.9700 |
C1—C7 | 1.504 (3) | C11—H11C | 0.9700 |
C2—H2A | 0.9300 | C11—H11D | 0.9700 |
C2—C3 | 1.382 (3) | C11—C12 | 1.508 (3) |
C3—H3 | 0.9300 | C12—H12A | 0.9700 |
C3—C4 | 1.378 (3) | C12—H12B | 0.9700 |
C4—C5 | 1.376 (3) | C12—C13 | 1.512 (3) |
C5—H5 | 0.9300 | C13—H13A | 0.9700 |
C5—C6 | 1.385 (3) | C13—H13B | 0.9700 |
C6—H6 | 0.9300 | C13—C14 | 1.515 (3) |
C7—H7A | 0.9600 | C14—H14A | 0.98 (3) |
C7—H7B | 0.9600 | C14—H14B | 0.95 (2) |
C7—H7C | 0.9600 | ||
O1—S1—N1 | 103.50 (9) | H9BC—C9—H9BD | 107.4 |
O1—S1—C4 | 109.43 (9) | C10A—C9—H9AA | 107.4 |
O2—S1—O1 | 119.67 (9) | C10A—C9—H9AB | 107.4 |
O2—S1—N1 | 109.00 (9) | C10B—C9—N3 | 116.2 (6) |
O2—S1—C4 | 108.91 (9) | C10B—C9—H9BC | 108.2 |
N1—S1—C4 | 105.34 (9) | C10B—C9—H9BD | 108.2 |
S1—N1—H1 | 117.6 (17) | C9—C10A—H10A | 108.7 |
C8—N1—S1 | 124.09 (15) | C9—C10A—H10B | 108.7 |
C8—N1—H1 | 116.6 (17) | C9—C10A—C11 | 114.4 (2) |
N3—N2—H2 | 121.4 (15) | H10A—C10A—H10B | 107.6 |
C8—N2—H2 | 117.1 (15) | C11—C10A—H10A | 108.7 |
C8—N2—N3 | 121.12 (17) | C11—C10A—H10B | 108.7 |
N2—N3—C9 | 110.35 (16) | C9—C10B—H10C | 108.2 |
N2—N3—C14 | 110.62 (17) | C9—C10B—H10D | 108.2 |
C9—N3—C14 | 115.46 (17) | C9—C10B—C11 | 116.2 (4) |
C2—C1—C6 | 117.79 (19) | H10C—C10B—H10D | 107.4 |
C2—C1—C7 | 121.25 (19) | C11—C10B—H10C | 108.2 |
C6—C1—C7 | 121.0 (2) | C11—C10B—H10D | 108.2 |
C1—C2—H2A | 118.9 | C10A—C11—H11A | 107.8 |
C1—C2—C3 | 122.12 (19) | C10A—C11—H11B | 107.8 |
C3—C2—H2A | 118.9 | C10B—C11—H11C | 108.1 |
C2—C3—H3 | 120.6 | C10B—C11—H11D | 108.1 |
C4—C3—C2 | 118.86 (19) | H11A—C11—H11B | 107.2 |
C4—C3—H3 | 120.6 | H11C—C11—H11D | 107.3 |
C3—C4—S1 | 119.76 (15) | C12—C11—C10A | 117.89 (19) |
C5—C4—S1 | 119.73 (14) | C12—C11—C10B | 116.7 (6) |
C5—C4—C3 | 120.48 (18) | C12—C11—H11A | 107.8 |
C4—C5—H5 | 120.2 | C12—C11—H11B | 107.8 |
C4—C5—C6 | 119.66 (18) | C12—C11—H11C | 108.1 |
C6—C5—H5 | 120.2 | C12—C11—H11D | 108.1 |
C1—C6—H6 | 119.5 | C11—C12—H12A | 107.9 |
C5—C6—C1 | 121.08 (19) | C11—C12—H12B | 107.9 |
C5—C6—H6 | 119.5 | C11—C12—C13 | 117.71 (18) |
C1—C7—H7A | 109.5 | H12A—C12—H12B | 107.2 |
C1—C7—H7B | 109.5 | C13—C12—H12A | 107.9 |
C1—C7—H7C | 109.5 | C13—C12—H12B | 107.9 |
H7A—C7—H7B | 109.5 | C12—C13—H13A | 108.6 |
H7A—C7—H7C | 109.5 | C12—C13—H13B | 108.6 |
H7B—C7—H7C | 109.5 | C12—C13—C14 | 114.55 (19) |
O3—C8—N1 | 122.08 (18) | H13A—C13—H13B | 107.6 |
O3—C8—N2 | 123.83 (18) | C14—C13—H13A | 108.6 |
N2—C8—N1 | 114.09 (18) | C14—C13—H13B | 108.6 |
N3—C9—H9AA | 107.4 | N3—C14—C13 | 117.15 (17) |
N3—C9—H9AB | 107.4 | N3—C14—H14A | 106.1 (14) |
N3—C9—H9BC | 108.2 | N3—C14—H14B | 105.8 (13) |
N3—C9—H9BD | 108.2 | C13—C14—H14A | 110.1 (14) |
N3—C9—C10A | 119.81 (18) | C13—C14—H14B | 108.7 (13) |
H9AA—C9—H9AB | 106.9 | H14A—C14—H14B | 108.6 (19) |
S1—N1—C8—O3 | 3.4 (3) | C2—C3—C4—S1 | 177.97 (16) |
S1—N1—C8—N2 | −176.96 (14) | C2—C3—C4—C5 | −0.3 (3) |
S1—C4—C5—C6 | −177.35 (16) | C3—C4—C5—C6 | 0.9 (3) |
O1—S1—N1—C8 | 172.54 (16) | C4—S1—N1—C8 | 57.67 (18) |
O1—S1—C4—C3 | −39.22 (18) | C4—C5—C6—C1 | −1.2 (3) |
O1—S1—C4—C5 | 139.02 (16) | C6—C1—C2—C3 | −0.1 (3) |
O2—S1—N1—C8 | −59.07 (18) | C7—C1—C2—C3 | 178.82 (19) |
O2—S1—C4—C3 | −171.72 (16) | C7—C1—C6—C5 | −178.2 (2) |
O2—S1—C4—C5 | 6.52 (19) | C8—N2—N3—C9 | 111.5 (2) |
N1—S1—C4—C3 | 71.48 (18) | C8—N2—N3—C14 | −119.5 (2) |
N1—S1—C4—C5 | −110.28 (17) | C9—N3—C14—C13 | 62.5 (3) |
N2—N3—C9—C10A | 74.0 (2) | C9—C10A—C11—C12 | −74.8 (3) |
N2—N3—C9—C10B | 140.6 (4) | C9—C10B—C11—C12 | 75.9 (10) |
N2—N3—C14—C13 | −63.7 (2) | C10A—C11—C12—C13 | 19.2 (3) |
N3—N2—C8—O3 | −177.07 (17) | C10B—C11—C12—C13 | −44.9 (4) |
N3—N2—C8—N1 | 3.3 (3) | C11—C12—C13—C14 | 51.8 (3) |
N3—C9—C10A—C11 | 73.5 (3) | C12—C13—C14—N3 | −85.1 (3) |
N3—C9—C10B—C11 | −78.9 (10) | C14—N3—C9—C10A | −52.3 (3) |
C1—C2—C3—C4 | −0.1 (3) | C14—N3—C9—C10B | 14.2 (4) |
C2—C1—C6—C5 | 0.8 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O3i | 0.82 (2) | 2.09 (2) | 2.906 (2) | 174 (2) |
Symmetry code: (i) −x, −y+1, −z+1. |
C14H21N3O3S | F(000) = 332 |
Mr = 311.40 | Dx = 1.368 Mg m−3 |
Triclinic, P1 | Melting point: 444 K |
a = 6.3064 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.1298 (7) Å | Cell parameters from 4645 reflections |
c = 13.3984 (11) Å | θ = 2.3–27.5° |
α = 79.397 (7)° | µ = 0.23 mm−1 |
β = 87.344 (7)° | T = 200 K |
γ = 85.986 (6)° | Block, colourless |
V = 755.95 (11) Å3 | 0.4 × 0.1 × 0.05 mm |
Z = 2 |
Xcalibur, Ruby, Gemini ultra diffractometer | 3090 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2455 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 26.4°, θmin = 2.3° |
ω scans | h = −7→7 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | k = −11→11 |
Tmin = 0.893, Tmax = 1.000 | l = −16→16 |
12156 measured reflections |
Refinement on F2 | 2 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.041 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.097 | w = 1/[σ2(Fo2) + (0.035P)2 + 0.314P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
3090 reflections | Δρmax = 0.32 e Å−3 |
218 parameters | Δρmin = −0.32 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 | 0.02035 (8) | 0.26832 (5) | 0.22422 (3) | 0.03102 (15) | |
O1 | 0.1403 (2) | 0.15420 (15) | 0.18212 (10) | 0.0416 (4) | |
O2 | −0.2054 (2) | 0.26795 (15) | 0.23202 (11) | 0.0408 (4) | |
O3 | −0.0705 (2) | 0.45561 (14) | 0.38268 (9) | 0.0333 (3) | |
N1 | 0.1133 (3) | 0.25089 (19) | 0.33872 (12) | 0.0326 (4) | |
H1 | 0.211 (3) | 0.195 (2) | 0.3524 (16) | 0.034 (6)* | |
N2 | 0.1613 (3) | 0.31804 (19) | 0.49204 (13) | 0.0352 (4) | |
H2 | 0.141 (3) | 0.376 (2) | 0.5319 (16) | 0.036 (6)* | |
N3 | 0.3181 (3) | 0.19895 (18) | 0.50988 (12) | 0.0333 (4) | |
C1 | 0.2033 (3) | 0.7202 (2) | 0.05218 (13) | 0.0313 (4) | |
C2 | 0.3546 (3) | 0.6041 (2) | 0.07783 (15) | 0.0382 (5) | |
H2A | 0.4961 | 0.6192 | 0.0586 | 0.046* | |
C3 | 0.3025 (3) | 0.4661 (2) | 0.13121 (15) | 0.0374 (5) | |
H3 | 0.4070 | 0.3894 | 0.1474 | 0.045* | |
C4 | 0.0924 (3) | 0.4444 (2) | 0.16000 (13) | 0.0270 (4) | |
C5 | −0.0626 (3) | 0.5580 (2) | 0.13624 (15) | 0.0362 (5) | |
H5 | −0.2035 | 0.5431 | 0.1567 | 0.043* | |
C6 | −0.0065 (3) | 0.6948 (2) | 0.08148 (15) | 0.0372 (5) | |
H6 | −0.1115 | 0.7708 | 0.0641 | 0.045* | |
C7 | 0.2648 (4) | 0.8701 (2) | −0.00409 (16) | 0.0458 (5) | |
H7A | 0.4045 | 0.8603 | −0.0347 | 0.069* | |
H7B | 0.2644 | 0.9384 | 0.0425 | 0.069* | |
H7C | 0.1647 | 0.9073 | −0.0560 | 0.069* | |
C8 | 0.0601 (3) | 0.3498 (2) | 0.40443 (13) | 0.0287 (4) | |
C9 | 0.5296 (3) | 0.2567 (2) | 0.51205 (15) | 0.0411 (5) | |
H9AA | 0.5446 | 0.3347 | 0.4528 | 0.049* | 0.854 (5) |
H9AB | 0.6343 | 0.1765 | 0.5036 | 0.049* | 0.854 (5) |
H9BC | 0.5111 | 0.3585 | 0.5240 | 0.049* | 0.146 (5) |
H9BD | 0.5990 | 0.2598 | 0.4456 | 0.049* | 0.146 (5) |
C10A | 0.5886 (4) | 0.3180 (3) | 0.60185 (18) | 0.0377 (7) | 0.854 (5) |
H10A | 0.4741 | 0.3872 | 0.6182 | 0.045* | 0.854 (5) |
H10B | 0.7143 | 0.3739 | 0.5839 | 0.045* | 0.854 (5) |
C10B | 0.6716 (16) | 0.1705 (13) | 0.5890 (4) | 0.042 (5) | 0.146 (5) |
H10C | 0.8171 | 0.1918 | 0.5680 | 0.050* | 0.146 (5) |
H10D | 0.6578 | 0.0651 | 0.5900 | 0.050* | 0.146 (5) |
C11 | 0.6327 (3) | 0.1997 (3) | 0.69638 (16) | 0.0450 (5) | |
H11A | 0.7244 | 0.1199 | 0.6758 | 0.054* | 0.854 (5) |
H11B | 0.7122 | 0.2443 | 0.7421 | 0.054* | 0.854 (5) |
H11C | 0.7592 | 0.1640 | 0.7343 | 0.054* | 0.146 (5) |
H11D | 0.6157 | 0.3069 | 0.6931 | 0.054* | 0.146 (5) |
C12 | 0.4436 (3) | 0.1305 (3) | 0.75573 (15) | 0.0426 (5) | |
H12A | 0.4171 | 0.1772 | 0.8149 | 0.051* | |
H12B | 0.4827 | 0.0258 | 0.7801 | 0.051* | |
C13 | 0.2367 (3) | 0.1404 (2) | 0.70079 (14) | 0.0345 (5) | |
H13A | 0.1355 | 0.0809 | 0.7444 | 0.041* | |
H13B | 0.1794 | 0.2433 | 0.6897 | 0.041 (6)* | |
C14 | 0.2561 (4) | 0.0885 (2) | 0.59945 (16) | 0.0391 (5) | |
H14A | 0.361 (4) | 0.004 (3) | 0.6033 (17) | 0.052 (7)* | |
H14B | 0.121 (4) | 0.054 (2) | 0.5847 (16) | 0.049 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0396 (3) | 0.0255 (3) | 0.0284 (3) | −0.0006 (2) | −0.0078 (2) | −0.00499 (19) |
O1 | 0.0606 (9) | 0.0301 (8) | 0.0360 (8) | 0.0061 (7) | −0.0098 (7) | −0.0125 (6) |
O2 | 0.0395 (8) | 0.0372 (8) | 0.0452 (8) | −0.0093 (6) | −0.0079 (6) | −0.0022 (7) |
O3 | 0.0382 (7) | 0.0307 (7) | 0.0295 (7) | 0.0058 (6) | −0.0024 (6) | −0.0044 (6) |
N1 | 0.0424 (10) | 0.0283 (9) | 0.0264 (9) | 0.0076 (8) | −0.0085 (7) | −0.0045 (7) |
N2 | 0.0495 (10) | 0.0300 (9) | 0.0268 (9) | 0.0095 (8) | −0.0071 (8) | −0.0096 (8) |
N3 | 0.0413 (9) | 0.0285 (9) | 0.0293 (9) | 0.0058 (7) | −0.0082 (7) | −0.0040 (7) |
C1 | 0.0389 (11) | 0.0336 (11) | 0.0227 (9) | −0.0052 (9) | −0.0042 (8) | −0.0061 (8) |
C2 | 0.0290 (10) | 0.0431 (12) | 0.0418 (12) | −0.0046 (9) | 0.0015 (9) | −0.0053 (10) |
C3 | 0.0319 (10) | 0.0362 (11) | 0.0425 (12) | 0.0064 (9) | −0.0030 (9) | −0.0053 (9) |
C4 | 0.0328 (10) | 0.0252 (9) | 0.0229 (9) | 0.0020 (8) | −0.0050 (7) | −0.0049 (7) |
C5 | 0.0287 (10) | 0.0375 (12) | 0.0393 (11) | 0.0013 (9) | −0.0017 (8) | 0.0003 (9) |
C6 | 0.0366 (11) | 0.0325 (11) | 0.0384 (11) | 0.0073 (9) | −0.0039 (9) | 0.0015 (9) |
C7 | 0.0545 (13) | 0.0407 (13) | 0.0413 (12) | −0.0130 (11) | −0.0065 (10) | 0.0003 (10) |
C8 | 0.0334 (10) | 0.0259 (10) | 0.0261 (10) | −0.0058 (8) | 0.0032 (8) | −0.0022 (8) |
C9 | 0.0438 (12) | 0.0433 (12) | 0.0341 (11) | −0.0020 (10) | −0.0010 (9) | −0.0018 (9) |
C10A | 0.0346 (13) | 0.0366 (15) | 0.0431 (15) | −0.0066 (10) | 0.0035 (10) | −0.0098 (11) |
C10B | 0.028 (7) | 0.066 (11) | 0.027 (8) | −0.009 (7) | −0.001 (6) | 0.001 (7) |
C11 | 0.0372 (11) | 0.0600 (15) | 0.0386 (12) | −0.0016 (10) | −0.0087 (9) | −0.0102 (11) |
C12 | 0.0419 (12) | 0.0520 (14) | 0.0308 (11) | 0.0047 (10) | −0.0034 (9) | −0.0016 (10) |
C13 | 0.0351 (10) | 0.0331 (11) | 0.0320 (11) | −0.0044 (9) | 0.0012 (8) | 0.0026 (8) |
C14 | 0.0506 (13) | 0.0267 (11) | 0.0397 (12) | −0.0059 (10) | −0.0123 (10) | −0.0010 (9) |
S1—O1 | 1.4291 (14) | C9—H9AA | 0.9700 |
S1—O2 | 1.4231 (14) | C9—H9AB | 0.9700 |
S1—N1 | 1.6441 (17) | C9—H9BC | 0.9700 |
S1—C4 | 1.7575 (19) | C9—H9BD | 0.9700 |
O3—C8 | 1.226 (2) | C9—C10A | 1.489 (3) |
N1—H1 | 0.78 (2) | C9—C10B | 1.474 (6) |
N1—C8 | 1.388 (2) | C10A—H10A | 0.9700 |
N2—H2 | 0.82 (2) | C10A—H10B | 0.9700 |
N2—N3 | 1.412 (2) | C10A—C11 | 1.528 (3) |
N2—C8 | 1.337 (2) | C10B—H10C | 0.9700 |
N3—C9 | 1.472 (3) | C10B—H10D | 0.9700 |
N3—C14 | 1.475 (3) | C10B—C11 | 1.516 (6) |
C1—C2 | 1.381 (3) | C11—H11A | 0.9700 |
C1—C6 | 1.385 (3) | C11—H11B | 0.9700 |
C1—C7 | 1.503 (3) | C11—H11C | 0.9700 |
C2—H2A | 0.9300 | C11—H11D | 0.9700 |
C2—C3 | 1.382 (3) | C11—C12 | 1.512 (3) |
C3—H3 | 0.9300 | C12—H12A | 0.9700 |
C3—C4 | 1.380 (3) | C12—H12B | 0.9700 |
C4—C5 | 1.377 (3) | C12—C13 | 1.517 (3) |
C5—H5 | 0.9300 | C13—H13A | 0.9700 |
C5—C6 | 1.387 (3) | C13—H13B | 0.9700 |
C6—H6 | 0.9300 | C13—C14 | 1.516 (3) |
C7—H7A | 0.9600 | C14—H14A | 0.97 (2) |
C7—H7B | 0.9600 | C14—H14B | 0.97 (2) |
C7—H7C | 0.9600 | ||
O1—S1—N1 | 103.45 (9) | H9AA—C9—H9AB | 106.9 |
O1—S1—C4 | 109.48 (9) | H9BC—C9—H9BD | 107.5 |
O2—S1—O1 | 119.71 (9) | C10A—C9—H9AA | 107.4 |
O2—S1—N1 | 108.97 (9) | C10A—C9—H9AB | 107.4 |
O2—S1—C4 | 108.95 (9) | C10B—C9—H9BC | 108.4 |
N1—S1—C4 | 105.26 (8) | C10B—C9—H9BD | 108.4 |
S1—N1—H1 | 117.7 (16) | C9—C10A—H10A | 108.7 |
C8—N1—S1 | 124.13 (15) | C9—C10A—H10B | 108.7 |
C8—N1—H1 | 116.7 (16) | C9—C10A—C11 | 114.25 (19) |
N3—N2—H2 | 120.4 (15) | H10A—C10A—H10B | 107.6 |
C8—N2—H2 | 118.1 (15) | C11—C10A—H10A | 108.7 |
C8—N2—N3 | 120.97 (16) | C11—C10A—H10B | 108.7 |
N2—N3—C9 | 110.30 (15) | C9—C10B—H10C | 108.3 |
N2—N3—C14 | 110.32 (16) | C9—C10B—H10D | 108.3 |
C9—N3—C14 | 115.72 (16) | C9—C10B—C11 | 115.9 (4) |
C2—C1—C6 | 117.85 (18) | H10C—C10B—H10D | 107.4 |
C2—C1—C7 | 121.05 (18) | C11—C10B—H10C | 108.3 |
C6—C1—C7 | 121.09 (19) | C11—C10B—H10D | 108.3 |
C1—C2—H2A | 118.9 | C10A—C11—H11A | 107.9 |
C1—C2—C3 | 122.11 (18) | C10A—C11—H11B | 107.9 |
C3—C2—H2A | 118.9 | C10B—C11—H11C | 108.1 |
C2—C3—H3 | 120.6 | C10B—C11—H11D | 108.1 |
C4—C3—C2 | 118.75 (18) | H11A—C11—H11B | 107.2 |
C4—C3—H3 | 120.6 | H11C—C11—H11D | 107.3 |
C3—C4—S1 | 119.70 (15) | C12—C11—C10A | 117.59 (18) |
C5—C4—S1 | 119.55 (14) | C12—C11—C10B | 117.0 (5) |
C5—C4—C3 | 120.71 (18) | C12—C11—H11A | 107.9 |
C4—C5—H5 | 120.3 | C12—C11—H11B | 107.9 |
C4—C5—C6 | 119.41 (17) | C12—C11—H11C | 108.1 |
C6—C5—H5 | 120.3 | C12—C11—H11D | 108.1 |
C1—C6—C5 | 121.15 (18) | C11—C12—H12A | 108.0 |
C1—C6—H6 | 119.4 | C11—C12—H12B | 108.0 |
C5—C6—H6 | 119.4 | C11—C12—C13 | 117.39 (17) |
C1—C7—H7A | 109.5 | H12A—C12—H12B | 107.2 |
C1—C7—H7B | 109.5 | C13—C12—H12A | 108.0 |
C1—C7—H7C | 109.5 | C13—C12—H12B | 108.0 |
H7A—C7—H7B | 109.5 | C12—C13—H13A | 108.6 |
H7A—C7—H7C | 109.5 | C12—C13—H13B | 108.6 |
H7B—C7—H7C | 109.5 | H13A—C13—H13B | 107.6 |
O3—C8—N1 | 121.79 (17) | C14—C13—C12 | 114.69 (18) |
O3—C8—N2 | 124.00 (17) | C14—C13—H13A | 108.6 |
N2—C8—N1 | 114.21 (17) | C14—C13—H13B | 108.6 |
N3—C9—H9AA | 107.4 | N3—C14—C13 | 117.02 (16) |
N3—C9—H9AB | 107.4 | N3—C14—H14A | 106.6 (13) |
N3—C9—H9BC | 108.4 | N3—C14—H14B | 106.4 (13) |
N3—C9—H9BD | 108.4 | C13—C14—H14A | 109.5 (13) |
N3—C9—C10A | 119.72 (17) | C13—C14—H14B | 109.3 (13) |
N3—C9—C10B | 115.4 (6) | H14A—C14—H14B | 107.6 (18) |
S1—N1—C8—O3 | 3.5 (3) | C2—C3—C4—S1 | 177.89 (15) |
S1—N1—C8—N2 | −177.18 (14) | C2—C3—C4—C5 | −0.1 (3) |
S1—C4—C5—C6 | −177.07 (15) | C3—C4—C5—C6 | 0.9 (3) |
O1—S1—N1—C8 | 172.53 (15) | C4—S1—N1—C8 | 57.66 (17) |
O1—S1—C4—C3 | −38.82 (18) | C4—C5—C6—C1 | −1.4 (3) |
O1—S1—C4—C5 | 139.22 (15) | C6—C1—C2—C3 | −0.2 (3) |
O2—S1—N1—C8 | −59.08 (17) | C7—C1—C2—C3 | 178.77 (18) |
O2—S1—C4—C3 | −171.45 (15) | C7—C1—C6—C5 | −177.93 (18) |
O2—S1—C4—C5 | 6.59 (18) | C8—N2—N3—C9 | 110.86 (19) |
N1—S1—C4—C3 | 71.80 (17) | C8—N2—N3—C14 | −120.05 (18) |
N1—S1—C4—C5 | −110.16 (16) | C9—N3—C14—C13 | 62.6 (2) |
N2—N3—C9—C10A | 74.4 (2) | C9—C10A—C11—C12 | −75.9 (3) |
N2—N3—C9—C10B | 141.1 (3) | C9—C10B—C11—C12 | 76.3 (10) |
N2—N3—C14—C13 | −63.5 (2) | C10A—C11—C12—C13 | 20.7 (3) |
N3—N2—C8—O3 | −176.64 (16) | C10B—C11—C12—C13 | −43.9 (4) |
N3—N2—C8—N1 | 4.0 (2) | C11—C12—C13—C14 | 51.0 (3) |
N3—C9—C10A—C11 | 73.2 (3) | C12—C13—C14—N3 | −85.3 (2) |
N3—C9—C10B—C11 | −80.0 (9) | C14—N3—C9—C10A | −51.7 (3) |
C1—C2—C3—C4 | −0.3 (3) | C14—N3—C9—C10B | 15.0 (4) |
C2—C1—C6—C5 | 1.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O3i | 0.82 (2) | 2.09 (2) | 2.905 (2) | 172 (2) |
Symmetry code: (i) −x, −y+1, −z+1. |
C14H21N3O3S | F(000) = 332 |
Mr = 311.40 | Dx = 1.380 Mg m−3 |
Triclinic, P1 | Melting point: 444 K |
a = 6.2891 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.0960 (4) Å | Cell parameters from 4856 reflections |
c = 13.3659 (5) Å | θ = 2.3–28.2° |
α = 79.436 (4)° | µ = 0.23 mm−1 |
β = 87.381 (3)° | T = 175 K |
γ = 86.026 (4)° | Block, colourless |
V = 749.41 (6) Å3 | 0.4 × 0.1 × 0.05 mm |
Z = 2 |
Xcalibur, Ruby, Gemini ultra diffractometer | 3064 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2504 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 26.4°, θmin = 1.6° |
ω scans | h = −7→7 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | k = −11→11 |
Tmin = 0.851, Tmax = 1.000 | l = −16→16 |
12090 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.039 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.095 | w = 1/[σ2(Fo2) + (0.0373P)2 + 0.3174P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
3064 reflections | Δρmax = 0.33 e Å−3 |
218 parameters | Δρmin = −0.35 e Å−3 |
2 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 | 0.02002 (7) | 0.26779 (5) | 0.22385 (3) | 0.02655 (14) | |
O1 | 0.1405 (2) | 0.15383 (14) | 0.18145 (10) | 0.0354 (3) | |
O2 | −0.2064 (2) | 0.26729 (15) | 0.23153 (10) | 0.0345 (3) | |
O3 | −0.07128 (19) | 0.45497 (14) | 0.38284 (9) | 0.0285 (3) | |
N1 | 0.1134 (3) | 0.24982 (18) | 0.33884 (12) | 0.0281 (4) | |
H1 | 0.211 (3) | 0.197 (2) | 0.3511 (16) | 0.032 (6)* | |
N2 | 0.1607 (3) | 0.31714 (18) | 0.49256 (12) | 0.0307 (4) | |
H2 | 0.141 (3) | 0.380 (3) | 0.5315 (16) | 0.038 (6)* | |
N3 | 0.3190 (2) | 0.19847 (17) | 0.50973 (11) | 0.0290 (4) | |
C1 | 0.2026 (3) | 0.7208 (2) | 0.05212 (13) | 0.0270 (4) | |
C2 | 0.3549 (3) | 0.6044 (2) | 0.07748 (14) | 0.0321 (4) | |
H2A | 0.4967 | 0.6197 | 0.0581 | 0.038* | |
C3 | 0.3027 (3) | 0.4658 (2) | 0.13083 (15) | 0.0315 (4) | |
H3 | 0.4074 | 0.3888 | 0.1470 | 0.038* | |
C4 | 0.0918 (3) | 0.44428 (19) | 0.15965 (13) | 0.0232 (4) | |
C5 | −0.0636 (3) | 0.5583 (2) | 0.13620 (14) | 0.0303 (4) | |
H5 | −0.2048 | 0.5431 | 0.1569 | 0.036* | |
C6 | −0.0079 (3) | 0.6953 (2) | 0.08171 (14) | 0.0321 (4) | |
H6 | −0.1133 | 0.7716 | 0.0646 | 0.039* | |
C7 | 0.2633 (3) | 0.8713 (2) | −0.00396 (15) | 0.0385 (5) | |
H7A | 0.4032 | 0.8618 | −0.0349 | 0.058* | |
H7B | 0.2632 | 0.9396 | 0.0429 | 0.058* | |
H7C | 0.1625 | 0.9086 | −0.0558 | 0.058* | |
C8 | 0.0594 (3) | 0.34913 (19) | 0.40446 (13) | 0.0236 (4) | |
C9 | 0.5309 (3) | 0.2571 (2) | 0.51145 (15) | 0.0356 (5) | |
H9AA | 0.5451 | 0.3357 | 0.4522 | 0.043* | 0.869 (5) |
H9AB | 0.6363 | 0.1771 | 0.5027 | 0.043* | 0.869 (5) |
H9BC | 0.5126 | 0.3590 | 0.5241 | 0.043* | 0.131 (5) |
H9BD | 0.6003 | 0.2607 | 0.4448 | 0.043* | 0.131 (5) |
C10A | 0.5897 (3) | 0.3186 (2) | 0.60211 (17) | 0.0318 (7) | 0.869 (5) |
H10A | 0.4741 | 0.3871 | 0.6190 | 0.038* | 0.869 (5) |
H10B | 0.7149 | 0.3757 | 0.5842 | 0.038* | 0.869 (5) |
C10B | 0.6723 (16) | 0.1684 (14) | 0.5888 (4) | 0.038 (5) | 0.131 (5) |
H10C | 0.8189 | 0.1872 | 0.5675 | 0.045* | 0.131 (5) |
H10D | 0.6546 | 0.0629 | 0.5902 | 0.045* | 0.131 (5) |
C11 | 0.6358 (3) | 0.1992 (2) | 0.69625 (15) | 0.0376 (5) | |
H11A | 0.7254 | 0.1187 | 0.6748 | 0.045* | 0.869 (5) |
H11B | 0.7181 | 0.2431 | 0.7417 | 0.045* | 0.869 (5) |
H11C | 0.6202 | 0.3069 | 0.6925 | 0.045* | 0.131 (5) |
H11D | 0.7629 | 0.1631 | 0.7340 | 0.045* | 0.131 (5) |
C12 | 0.4453 (3) | 0.1310 (2) | 0.75679 (15) | 0.0362 (5) | |
H12A | 0.4838 | 0.0262 | 0.7824 | 0.043* | |
H12B | 0.4187 | 0.1797 | 0.8153 | 0.043* | |
C13 | 0.2385 (3) | 0.1403 (2) | 0.70126 (14) | 0.0297 (4) | |
H13A | 0.1809 | 0.2435 | 0.6899 | 0.036* | |
H13B | 0.1368 | 0.0807 | 0.7449 | 0.042 (6)* | |
C14 | 0.2586 (4) | 0.0875 (2) | 0.59955 (15) | 0.0337 (5) | |
H14A | 0.364 (3) | 0.003 (3) | 0.6040 (15) | 0.038 (6)* | |
H14B | 0.123 (3) | 0.053 (2) | 0.5850 (16) | 0.041 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0336 (3) | 0.0221 (2) | 0.0243 (2) | −0.00045 (18) | −0.00668 (18) | −0.00444 (18) |
O1 | 0.0525 (8) | 0.0252 (7) | 0.0300 (7) | 0.0056 (6) | −0.0083 (6) | −0.0105 (6) |
O2 | 0.0330 (7) | 0.0309 (8) | 0.0389 (8) | −0.0073 (6) | −0.0067 (6) | −0.0014 (6) |
O3 | 0.0326 (7) | 0.0265 (7) | 0.0255 (7) | 0.0047 (6) | −0.0019 (5) | −0.0047 (5) |
N1 | 0.0353 (9) | 0.0237 (9) | 0.0246 (8) | 0.0068 (7) | −0.0071 (7) | −0.0044 (7) |
N2 | 0.0419 (9) | 0.0265 (9) | 0.0243 (8) | 0.0081 (7) | −0.0060 (7) | −0.0088 (7) |
N3 | 0.0352 (9) | 0.0249 (8) | 0.0261 (8) | 0.0052 (7) | −0.0069 (7) | −0.0040 (6) |
C1 | 0.0332 (10) | 0.0294 (10) | 0.0194 (9) | −0.0051 (8) | −0.0033 (7) | −0.0053 (7) |
C2 | 0.0242 (9) | 0.0377 (11) | 0.0342 (11) | −0.0040 (8) | 0.0021 (8) | −0.0064 (9) |
C3 | 0.0270 (10) | 0.0307 (11) | 0.0359 (11) | 0.0058 (8) | −0.0033 (8) | −0.0057 (9) |
C4 | 0.0280 (9) | 0.0227 (9) | 0.0196 (8) | 0.0005 (7) | −0.0045 (7) | −0.0053 (7) |
C5 | 0.0231 (9) | 0.0318 (11) | 0.0330 (10) | 0.0011 (8) | −0.0001 (8) | 0.0005 (8) |
C6 | 0.0306 (10) | 0.0279 (10) | 0.0343 (11) | 0.0056 (8) | −0.0026 (8) | 0.0012 (8) |
C7 | 0.0456 (12) | 0.0348 (12) | 0.0345 (11) | −0.0106 (9) | −0.0045 (9) | −0.0007 (9) |
C8 | 0.0276 (9) | 0.0206 (9) | 0.0222 (9) | −0.0030 (7) | 0.0031 (7) | −0.0029 (7) |
C9 | 0.0374 (11) | 0.0377 (12) | 0.0299 (10) | −0.0030 (9) | −0.0006 (8) | −0.0015 (9) |
C10A | 0.0287 (12) | 0.0301 (13) | 0.0376 (13) | −0.0047 (9) | 0.0031 (9) | −0.0083 (10) |
C10B | 0.017 (7) | 0.062 (12) | 0.028 (8) | −0.006 (7) | −0.003 (6) | 0.010 (7) |
C11 | 0.0305 (10) | 0.0497 (13) | 0.0334 (11) | −0.0017 (9) | −0.0073 (8) | −0.0086 (10) |
C12 | 0.0353 (11) | 0.0448 (12) | 0.0263 (10) | 0.0038 (9) | −0.0031 (8) | −0.0028 (9) |
C13 | 0.0296 (10) | 0.0274 (10) | 0.0290 (10) | −0.0035 (8) | 0.0006 (8) | 0.0030 (8) |
C14 | 0.0424 (12) | 0.0236 (10) | 0.0357 (11) | −0.0050 (9) | −0.0096 (9) | −0.0037 (8) |
S1—O1 | 1.4273 (14) | C9—H9AA | 0.9700 |
S1—O2 | 1.4236 (13) | C9—H9AB | 0.9700 |
S1—N1 | 1.6464 (16) | C9—H9BC | 0.9700 |
S1—C4 | 1.7543 (18) | C9—H9BD | 0.9700 |
O3—C8 | 1.223 (2) | C9—C10A | 1.495 (3) |
N1—H1 | 0.76 (2) | C9—C10B | 1.480 (5) |
N1—C8 | 1.386 (2) | C10A—H10A | 0.9700 |
N2—H2 | 0.84 (2) | C10A—H10B | 0.9700 |
N2—N3 | 1.411 (2) | C10A—C11 | 1.528 (3) |
N2—C8 | 1.339 (2) | C10B—H10C | 0.9700 |
N3—C9 | 1.472 (2) | C10B—H10D | 0.9700 |
N3—C14 | 1.474 (2) | C10B—C11 | 1.517 (6) |
C1—C2 | 1.382 (3) | C11—H11A | 0.9700 |
C1—C6 | 1.387 (2) | C11—H11B | 0.9700 |
C1—C7 | 1.500 (3) | C11—H11C | 0.9700 |
C2—H2A | 0.9300 | C11—H11D | 0.9700 |
C2—C3 | 1.382 (3) | C11—C12 | 1.519 (3) |
C3—H3 | 0.9300 | C12—H12A | 0.9700 |
C3—C4 | 1.381 (2) | C12—H12B | 0.9700 |
C4—C5 | 1.377 (3) | C12—C13 | 1.516 (3) |
C5—H5 | 0.9300 | C13—H13A | 0.9700 |
C5—C6 | 1.383 (3) | C13—H13B | 0.9700 |
C6—H6 | 0.9300 | C13—C14 | 1.520 (3) |
C7—H7A | 0.9600 | C14—H14A | 0.98 (2) |
C7—H7B | 0.9600 | C14—H14B | 0.97 (2) |
C7—H7C | 0.9600 | ||
O1—S1—N1 | 103.40 (8) | H9AA—C9—H9AB | 107.0 |
O1—S1—C4 | 109.33 (8) | H9BC—C9—H9BD | 107.6 |
O2—S1—O1 | 119.78 (8) | C10A—C9—H9AA | 107.5 |
O2—S1—N1 | 109.02 (8) | C10A—C9—H9AB | 107.5 |
O2—S1—C4 | 108.88 (8) | C10B—C9—H9BC | 108.7 |
N1—S1—C4 | 105.44 (8) | C10B—C9—H9BD | 108.7 |
S1—N1—H1 | 117.2 (16) | C9—C10A—H10A | 108.7 |
C8—N1—S1 | 123.79 (14) | C9—C10A—H10B | 108.7 |
C8—N1—H1 | 117.2 (16) | C9—C10A—C11 | 114.09 (18) |
N3—N2—H2 | 122.0 (15) | H10A—C10A—H10B | 107.6 |
C8—N2—H2 | 116.4 (15) | C11—C10A—H10A | 108.7 |
C8—N2—N3 | 120.74 (15) | C11—C10A—H10B | 108.7 |
N2—N3—C9 | 110.48 (15) | C9—C10B—H10C | 108.4 |
N2—N3—C14 | 110.16 (15) | C9—C10B—H10D | 108.4 |
C9—N3—C14 | 115.63 (15) | C9—C10B—C11 | 115.7 (4) |
C2—C1—C6 | 118.02 (17) | H10C—C10B—H10D | 107.4 |
C2—C1—C7 | 121.11 (17) | C11—C10B—H10C | 108.4 |
C6—C1—C7 | 120.86 (18) | C11—C10B—H10D | 108.4 |
C1—C2—H2A | 119.0 | C10A—C11—H11A | 108.0 |
C1—C2—C3 | 121.97 (17) | C10A—C11—H11B | 108.0 |
C3—C2—H2A | 119.0 | C10B—C11—H11C | 108.1 |
C2—C3—H3 | 120.7 | C10B—C11—H11D | 108.1 |
C4—C3—C2 | 118.60 (17) | C10B—C11—C12 | 116.8 (6) |
C4—C3—H3 | 120.7 | H11A—C11—H11B | 107.3 |
C3—C4—S1 | 119.52 (14) | H11C—C11—H11D | 107.3 |
C5—C4—S1 | 119.56 (13) | C12—C11—C10A | 117.15 (17) |
C5—C4—C3 | 120.89 (17) | C12—C11—H11A | 108.0 |
C4—C5—H5 | 120.3 | C12—C11—H11B | 108.0 |
C4—C5—C6 | 119.47 (16) | C12—C11—H11C | 108.1 |
C6—C5—H5 | 120.3 | C12—C11—H11D | 108.1 |
C1—C6—H6 | 119.5 | C11—C12—H12A | 108.1 |
C5—C6—C1 | 121.03 (17) | C11—C12—H12B | 108.1 |
C5—C6—H6 | 119.5 | H12A—C12—H12B | 107.3 |
C1—C7—H7A | 109.5 | C13—C12—C11 | 116.96 (16) |
C1—C7—H7B | 109.5 | C13—C12—H12A | 108.1 |
C1—C7—H7C | 109.5 | C13—C12—H12B | 108.1 |
H7A—C7—H7B | 109.5 | C12—C13—H13A | 108.6 |
H7A—C7—H7C | 109.5 | C12—C13—H13B | 108.6 |
H7B—C7—H7C | 109.5 | C12—C13—C14 | 114.85 (16) |
O3—C8—N1 | 122.06 (16) | H13A—C13—H13B | 107.5 |
O3—C8—N2 | 123.92 (16) | C14—C13—H13A | 108.6 |
N2—C8—N1 | 114.02 (16) | C14—C13—H13B | 108.6 |
N3—C9—H9AA | 107.5 | N3—C14—C13 | 116.92 (15) |
N3—C9—H9AB | 107.5 | N3—C14—H14A | 107.1 (12) |
N3—C9—H9BC | 108.7 | N3—C14—H14B | 106.2 (13) |
N3—C9—H9BD | 108.7 | C13—C14—H14A | 109.3 (12) |
N3—C9—C10A | 119.37 (16) | C13—C14—H14B | 109.0 (12) |
N3—C9—C10B | 114.3 (6) | H14A—C14—H14B | 107.9 (17) |
S1—N1—C8—O3 | 3.5 (2) | C2—C3—C4—S1 | 177.97 (14) |
S1—N1—C8—N2 | −177.23 (13) | C2—C3—C4—C5 | −0.2 (3) |
S1—C4—C5—C6 | −177.19 (14) | C3—C4—C5—C6 | 1.0 (3) |
O1—S1—N1—C8 | 172.42 (15) | C4—S1—N1—C8 | 57.66 (17) |
O1—S1—C4—C3 | −38.80 (17) | C4—C5—C6—C1 | −1.4 (3) |
O1—S1—C4—C5 | 139.44 (14) | C6—C1—C2—C3 | −0.1 (3) |
O2—S1—N1—C8 | −59.11 (17) | C7—C1—C2—C3 | 178.73 (17) |
O2—S1—C4—C3 | −171.35 (14) | C7—C1—C6—C5 | −177.94 (17) |
O2—S1—C4—C5 | 6.88 (17) | C8—N2—N3—C9 | 110.31 (18) |
N1—S1—C4—C3 | 71.79 (16) | C8—N2—N3—C14 | −120.71 (17) |
N1—S1—C4—C5 | −109.98 (15) | C9—N3—C14—C13 | 63.1 (2) |
N2—N3—C9—C10A | 74.3 (2) | C9—C10A—C11—C12 | −77.4 (2) |
N2—N3—C9—C10B | 141.2 (3) | C9—C10B—C11—C12 | 77.2 (10) |
N2—N3—C14—C13 | −63.1 (2) | C10A—C11—C12—C13 | 22.3 (3) |
N3—N2—C8—O3 | −176.13 (16) | C10B—C11—C12—C13 | −43.1 (4) |
N3—N2—C8—N1 | 4.6 (2) | C11—C12—C13—C14 | 50.2 (2) |
N3—C9—C10A—C11 | 73.5 (2) | C12—C13—C14—N3 | −85.9 (2) |
N3—C9—C10B—C11 | −81.4 (10) | C14—N3—C9—C10A | −51.6 (2) |
C1—C2—C3—C4 | −0.2 (3) | C14—N3—C9—C10B | 15.2 (4) |
C2—C1—C6—C5 | 0.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O3i | 0.84 (2) | 2.06 (2) | 2.899 (2) | 174 (2) |
Symmetry code: (i) −x, −y+1, −z+1. |
C14H21N3O3S | F(000) = 332 |
Mr = 311.40 | Dx = 1.388 Mg m−3 |
Triclinic, P1 | Melting point: 444 K |
a = 6.2738 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.0824 (4) Å | Cell parameters from 5119 reflections |
c = 13.3414 (5) Å | θ = 2.3–28.8° |
α = 79.449 (4)° | µ = 0.23 mm−1 |
β = 87.415 (3)° | T = 150 K |
γ = 86.013 (4)° | Block, colourless |
V = 745.14 (6) Å3 | 0.4 × 0.1 × 0.05 mm |
Z = 2 |
Xcalibur, Ruby, Gemini ultra diffractometer | 3045 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2540 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 26.4°, θmin = 1.6° |
ω scans | h = −7→7 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | k = −11→11 |
Tmin = 0.927, Tmax = 1.000 | l = −16→16 |
12009 measured reflections |
Refinement on F2 | 2 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.038 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.093 | w = 1/[σ2(Fo2) + (0.0382P)2 + 0.2704P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
3045 reflections | Δρmax = 0.43 e Å−3 |
218 parameters | Δρmin = −0.39 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 | 0.98036 (7) | 0.73262 (5) | 0.77641 (3) | 0.02242 (13) | |
O1 | 0.8593 (2) | 0.84664 (14) | 0.81909 (9) | 0.0297 (3) | |
O2 | 1.20715 (19) | 0.73324 (14) | 0.76890 (9) | 0.0292 (3) | |
O3 | 1.07216 (18) | 0.54545 (13) | 0.61691 (9) | 0.0242 (3) | |
N1 | 0.8871 (3) | 0.75066 (17) | 0.66118 (11) | 0.0237 (3) | |
H1 | 0.790 (3) | 0.805 (2) | 0.6486 (16) | 0.029 (6)* | |
N2 | 0.8400 (2) | 0.68383 (17) | 0.50685 (12) | 0.0260 (3) | |
H2 | 0.859 (3) | 0.623 (2) | 0.4672 (16) | 0.030 (5)* | |
N3 | 0.6802 (2) | 0.80220 (16) | 0.49024 (11) | 0.0244 (3) | |
C1 | 0.7980 (3) | 0.2788 (2) | 0.94811 (12) | 0.0228 (4) | |
C2 | 0.6452 (3) | 0.3953 (2) | 0.92270 (14) | 0.0272 (4) | |
H2A | 0.5031 | 0.3798 | 0.9420 | 0.033* | |
C3 | 0.6972 (3) | 0.5341 (2) | 0.86946 (14) | 0.0262 (4) | |
H3 | 0.5923 | 0.6113 | 0.8535 | 0.031* | |
C4 | 0.9088 (3) | 0.55568 (19) | 0.84036 (12) | 0.0200 (4) | |
C5 | 1.0651 (3) | 0.4413 (2) | 0.86356 (13) | 0.0257 (4) | |
H5 | 1.2066 | 0.4564 | 0.8427 | 0.031* | |
C6 | 1.0091 (3) | 0.3040 (2) | 0.91813 (13) | 0.0267 (4) | |
H6 | 1.1146 | 0.2274 | 0.9350 | 0.032* | |
C7 | 0.7372 (3) | 0.1277 (2) | 1.00388 (14) | 0.0322 (4) | |
H7A | 0.5978 | 0.1373 | 1.0357 | 0.048* | |
H7B | 0.8394 | 0.0894 | 1.0551 | 0.048* | |
H7C | 0.7354 | 0.0600 | 0.9565 | 0.048* | |
C8 | 0.9412 (3) | 0.65192 (18) | 0.59529 (12) | 0.0201 (4) | |
C9 | 0.4679 (3) | 0.7426 (2) | 0.48880 (14) | 0.0300 (4) | |
H9AA | 0.3616 | 0.8224 | 0.4976 | 0.036* | 0.894 (5) |
H9AB | 0.4544 | 0.6638 | 0.5481 | 0.036* | 0.894 (5) |
H9BC | 0.3988 | 0.7381 | 0.5557 | 0.036* | 0.106 (5) |
H9BD | 0.4864 | 0.6409 | 0.4755 | 0.036* | 0.106 (5) |
C10A | 0.4096 (3) | 0.6805 (2) | 0.39756 (15) | 0.0268 (6) | 0.894 (5) |
H10A | 0.2851 | 0.6223 | 0.4155 | 0.032* | 0.894 (5) |
H10B | 0.5265 | 0.6131 | 0.3803 | 0.032* | 0.894 (5) |
C10B | 0.325 (2) | 0.8331 (16) | 0.4112 (4) | 0.039 (6) | 0.106 (5) |
H10C | 0.3444 | 0.9386 | 0.4096 | 0.047* | 0.106 (5) |
H10D | 0.1779 | 0.8152 | 0.4327 | 0.047* | 0.106 (5) |
C11 | 0.3613 (3) | 0.8007 (2) | 0.30379 (14) | 0.0307 (4) | |
H11A | 0.2770 | 0.7575 | 0.2587 | 0.037* | 0.894 (5) |
H11B | 0.2731 | 0.8816 | 0.3259 | 0.037* | 0.894 (5) |
H11C | 0.2338 | 0.8364 | 0.2659 | 0.037* | 0.106 (5) |
H11D | 0.3768 | 0.6927 | 0.3082 | 0.037* | 0.106 (5) |
C12 | 0.5528 (3) | 0.8683 (2) | 0.24229 (14) | 0.0300 (4) | |
H12A | 0.5795 | 0.8182 | 0.1842 | 0.036* | |
H12B | 0.5143 | 0.9730 | 0.2158 | 0.036* | |
C13 | 0.7605 (3) | 0.8598 (2) | 0.29827 (13) | 0.0246 (4) | |
H13A | 0.8624 | 0.9194 | 0.2545 | 0.030* | |
H13B | 0.8186 | 0.7566 | 0.3102 | 0.031 (5)* | |
C14 | 0.7391 (3) | 0.9139 (2) | 0.39992 (14) | 0.0282 (4) | |
H14A | 0.632 (3) | 0.995 (2) | 0.3970 (15) | 0.031 (5)* | |
H14B | 0.875 (3) | 0.951 (2) | 0.4164 (15) | 0.034 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0280 (2) | 0.0189 (2) | 0.0207 (2) | −0.00046 (17) | −0.00564 (17) | −0.00375 (17) |
O1 | 0.0437 (8) | 0.0216 (7) | 0.0251 (7) | 0.0051 (6) | −0.0074 (6) | −0.0087 (5) |
O2 | 0.0284 (7) | 0.0263 (7) | 0.0323 (7) | −0.0062 (5) | −0.0059 (5) | −0.0008 (6) |
O3 | 0.0279 (6) | 0.0215 (7) | 0.0221 (6) | 0.0039 (5) | −0.0015 (5) | −0.0031 (5) |
N1 | 0.0301 (8) | 0.0202 (8) | 0.0200 (8) | 0.0063 (7) | −0.0062 (6) | −0.0033 (6) |
N2 | 0.0344 (9) | 0.0225 (8) | 0.0216 (8) | 0.0070 (7) | −0.0045 (6) | −0.0079 (7) |
N3 | 0.0280 (8) | 0.0221 (8) | 0.0224 (8) | 0.0044 (6) | −0.0069 (6) | −0.0030 (6) |
C1 | 0.0284 (9) | 0.0247 (9) | 0.0166 (8) | −0.0040 (7) | −0.0030 (7) | −0.0057 (7) |
C2 | 0.0206 (9) | 0.0322 (11) | 0.0290 (10) | −0.0041 (7) | 0.0017 (7) | −0.0056 (8) |
C3 | 0.0229 (9) | 0.0249 (10) | 0.0299 (10) | 0.0058 (7) | −0.0027 (7) | −0.0048 (8) |
C4 | 0.0248 (9) | 0.0194 (9) | 0.0162 (8) | 0.0000 (7) | −0.0032 (7) | −0.0044 (7) |
C5 | 0.0209 (9) | 0.0266 (10) | 0.0275 (10) | 0.0006 (7) | −0.0011 (7) | −0.0002 (8) |
C6 | 0.0258 (9) | 0.0239 (10) | 0.0275 (10) | 0.0057 (7) | −0.0030 (7) | 0.0005 (8) |
C7 | 0.0376 (11) | 0.0294 (11) | 0.0289 (10) | −0.0088 (8) | −0.0034 (8) | −0.0006 (8) |
C8 | 0.0236 (8) | 0.0177 (9) | 0.0182 (8) | −0.0026 (7) | 0.0026 (7) | −0.0014 (7) |
C9 | 0.0313 (10) | 0.0312 (10) | 0.0260 (10) | −0.0001 (8) | −0.0007 (8) | −0.0021 (8) |
C10A | 0.0238 (11) | 0.0254 (12) | 0.0321 (12) | −0.0049 (8) | 0.0025 (8) | −0.0071 (9) |
C10B | 0.018 (9) | 0.063 (15) | 0.030 (11) | −0.007 (9) | 0.002 (7) | 0.011 (9) |
C11 | 0.0245 (9) | 0.0407 (12) | 0.0283 (10) | −0.0002 (8) | −0.0051 (8) | −0.0092 (9) |
C12 | 0.0296 (10) | 0.0375 (11) | 0.0214 (9) | 0.0031 (8) | −0.0022 (7) | −0.0027 (8) |
C13 | 0.0242 (9) | 0.0234 (10) | 0.0238 (9) | −0.0031 (7) | −0.0002 (7) | 0.0026 (7) |
C14 | 0.0350 (11) | 0.0206 (10) | 0.0294 (10) | −0.0032 (8) | −0.0090 (8) | −0.0025 (8) |
S1—O1 | 1.4288 (13) | C9—H9AA | 0.9700 |
S1—O2 | 1.4222 (13) | C9—H9AB | 0.9700 |
S1—N1 | 1.6456 (15) | C9—H9BC | 0.9700 |
S1—C4 | 1.7537 (17) | C9—H9BD | 0.9700 |
O3—C8 | 1.226 (2) | C9—C10A | 1.501 (3) |
N1—H1 | 0.76 (2) | C9—C10B | 1.490 (6) |
N1—C8 | 1.383 (2) | C10A—H10A | 0.9700 |
N2—H2 | 0.83 (2) | C10A—H10B | 0.9700 |
N2—N3 | 1.412 (2) | C10A—C11 | 1.529 (3) |
N2—C8 | 1.340 (2) | C10B—H10C | 0.9700 |
N3—C9 | 1.475 (2) | C10B—H10D | 0.9700 |
N3—C14 | 1.477 (2) | C10B—C11 | 1.519 (6) |
C1—C2 | 1.383 (3) | C11—H11A | 0.9700 |
C1—C6 | 1.388 (2) | C11—H11B | 0.9700 |
C1—C7 | 1.501 (2) | C11—H11C | 0.9700 |
C2—H2A | 0.9300 | C11—H11D | 0.9700 |
C2—C3 | 1.381 (3) | C11—C12 | 1.524 (2) |
C3—H3 | 0.9300 | C12—H12A | 0.9700 |
C3—C4 | 1.383 (2) | C12—H12B | 0.9700 |
C4—C5 | 1.380 (2) | C12—C13 | 1.521 (2) |
C5—H5 | 0.9300 | C13—H13A | 0.9700 |
C5—C6 | 1.384 (2) | C13—H13B | 0.9700 |
C6—H6 | 0.9300 | C13—C14 | 1.522 (3) |
C7—H7A | 0.9600 | C14—H14A | 0.96 (2) |
C7—H7B | 0.9600 | C14—H14B | 0.99 (2) |
C7—H7C | 0.9600 | ||
O1—S1—N1 | 103.50 (8) | H9AA—C9—H9AB | 107.0 |
O1—S1—C4 | 109.38 (8) | H9BC—C9—H9BD | 107.7 |
O2—S1—O1 | 119.76 (8) | C10A—C9—H9AA | 107.5 |
O2—S1—N1 | 108.99 (8) | C10A—C9—H9AB | 107.5 |
O2—S1—C4 | 108.83 (8) | C10B—C9—H9BC | 108.8 |
N1—S1—C4 | 105.39 (8) | C10B—C9—H9BD | 108.8 |
S1—N1—H1 | 117.1 (16) | C9—C10A—H10A | 108.8 |
C8—N1—S1 | 124.01 (13) | C9—C10A—H10B | 108.8 |
C8—N1—H1 | 117.2 (16) | C9—C10A—C11 | 113.79 (16) |
N3—N2—H2 | 121.1 (14) | H10A—C10A—H10B | 107.7 |
C8—N2—H2 | 117.6 (14) | C11—C10A—H10A | 108.8 |
C8—N2—N3 | 120.41 (14) | C11—C10A—H10B | 108.8 |
N2—N3—C9 | 110.48 (14) | C9—C10B—H10C | 108.5 |
N2—N3—C14 | 110.10 (14) | C9—C10B—H10D | 108.5 |
C9—N3—C14 | 115.52 (14) | C9—C10B—C11 | 115.0 (4) |
C2—C1—C6 | 118.08 (16) | H10C—C10B—H10D | 107.5 |
C2—C1—C7 | 121.10 (16) | C11—C10B—H10C | 108.5 |
C6—C1—C7 | 120.80 (16) | C11—C10B—H10D | 108.5 |
C1—C2—H2A | 119.0 | C10A—C11—H11A | 108.1 |
C3—C2—C1 | 122.00 (16) | C10A—C11—H11B | 108.1 |
C3—C2—H2A | 119.0 | C10B—C11—H11C | 108.0 |
C2—C3—H3 | 120.7 | C10B—C11—H11D | 108.0 |
C2—C3—C4 | 118.57 (16) | C10B—C11—C12 | 117.0 (7) |
C4—C3—H3 | 120.7 | H11A—C11—H11B | 107.3 |
C3—C4—S1 | 119.45 (13) | H11C—C11—H11D | 107.3 |
C5—C4—S1 | 119.57 (12) | C12—C11—C10A | 116.78 (16) |
C5—C4—C3 | 120.94 (16) | C12—C11—H11A | 108.1 |
C4—C5—H5 | 120.3 | C12—C11—H11B | 108.1 |
C4—C5—C6 | 119.32 (15) | C12—C11—H11C | 108.0 |
C6—C5—H5 | 120.3 | C12—C11—H11D | 108.0 |
C1—C6—H6 | 119.5 | C11—C12—H12A | 108.1 |
C5—C6—C1 | 121.08 (16) | C11—C12—H12B | 108.1 |
C5—C6—H6 | 119.5 | H12A—C12—H12B | 107.3 |
C1—C7—H7A | 109.5 | C13—C12—C11 | 116.71 (15) |
C1—C7—H7B | 109.5 | C13—C12—H12A | 108.1 |
C1—C7—H7C | 109.5 | C13—C12—H12B | 108.1 |
H7A—C7—H7B | 109.5 | C12—C13—H13A | 108.6 |
H7A—C7—H7C | 109.5 | C12—C13—H13B | 108.6 |
H7B—C7—H7C | 109.5 | C12—C13—C14 | 114.74 (15) |
O3—C8—N1 | 122.01 (15) | H13A—C13—H13B | 107.6 |
O3—C8—N2 | 123.68 (15) | C14—C13—H13A | 108.6 |
N2—C8—N1 | 114.31 (15) | C14—C13—H13B | 108.6 |
N3—C9—H9AA | 107.5 | N3—C14—C13 | 116.65 (15) |
N3—C9—H9AB | 107.5 | N3—C14—H14A | 105.8 (12) |
N3—C9—H9BC | 108.8 | N3—C14—H14B | 105.3 (12) |
N3—C9—H9BD | 108.8 | C13—C14—H14A | 110.4 (12) |
N3—C9—C10A | 119.13 (15) | C13—C14—H14B | 110.6 (11) |
N3—C9—C10B | 113.9 (7) | H14A—C14—H14B | 107.6 (16) |
S1—N1—C8—O3 | −3.3 (2) | C2—C3—C4—S1 | −177.89 (13) |
S1—N1—C8—N2 | 177.23 (12) | C2—C3—C4—C5 | 0.2 (3) |
S1—C4—C5—C6 | 177.05 (13) | C3—C4—C5—C6 | −1.0 (3) |
O1—S1—N1—C8 | −172.43 (14) | C4—S1—N1—C8 | −57.59 (16) |
O1—S1—C4—C3 | 38.55 (16) | C4—C5—C6—C1 | 1.2 (3) |
O1—S1—C4—C5 | −139.55 (14) | C6—C1—C2—C3 | −0.3 (3) |
O2—S1—N1—C8 | 59.07 (16) | C7—C1—C2—C3 | −178.55 (16) |
O2—S1—C4—C3 | 171.07 (13) | C7—C1—C6—C5 | 177.68 (16) |
O2—S1—C4—C5 | −7.03 (16) | C8—N2—N3—C9 | −109.99 (17) |
N1—S1—C4—C3 | −72.15 (15) | C8—N2—N3—C14 | 121.22 (16) |
N1—S1—C4—C5 | 109.74 (15) | C9—N3—C14—C13 | −63.6 (2) |
N2—N3—C9—C10A | −74.0 (2) | C9—C10A—C11—C12 | 78.6 (2) |
N2—N3—C9—C10B | −141.4 (3) | C9—C10B—C11—C12 | −77.7 (12) |
N2—N3—C14—C13 | 62.4 (2) | C10A—C11—C12—C13 | −23.5 (2) |
N3—N2—C8—O3 | 175.57 (15) | C10B—C11—C12—C13 | 42.9 (4) |
N3—N2—C8—N1 | −5.0 (2) | C11—C12—C13—C14 | −49.7 (2) |
N3—C9—C10A—C11 | −73.9 (2) | C12—C13—C14—N3 | 86.5 (2) |
N3—C9—C10B—C11 | 82.2 (12) | C14—N3—C9—C10A | 51.7 (2) |
C1—C2—C3—C4 | 0.5 (3) | C14—N3—C9—C10B | −15.6 (4) |
C2—C1—C6—C5 | −0.6 (3) |
C14H21N3O3S | F(000) = 332 |
Mr = 311.40 | Dx = 1.394 Mg m−3 |
Triclinic, P1 | Melting point: 444 K |
a = 6.2586 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.0748 (4) Å | Cell parameters from 5366 reflections |
c = 13.3249 (5) Å | θ = 2.3–28.8° |
α = 79.432 (3)° | µ = 0.23 mm−1 |
β = 87.442 (3)° | T = 125 K |
γ = 85.975 (3)° | Block, colourless |
V = 741.73 (5) Å3 | 0.4 × 0.1 × 0.05 mm |
Z = 2 |
Xcalibur, Ruby, Gemini ultra diffractometer | 3037 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2585 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 26.4°, θmin = 1.6° |
ω scans | h = −7→7 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | k = −11→11 |
Tmin = 0.894, Tmax = 1.000 | l = −16→16 |
11961 measured reflections |
Refinement on F2 | 2 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.036 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.086 | w = 1/[σ2(Fo2) + (0.0337P)2 + 0.3459P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
3037 reflections | Δρmax = 0.40 e Å−3 |
213 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 | Occ. (<1) | |
S1 | 0.01918 (6) | 0.26706 (4) | 0.22345 (3) | 0.01862 (12) | |
O1 | 0.14089 (19) | 0.15310 (13) | 0.18063 (9) | 0.0250 (3) | |
O2 | −0.20835 (18) | 0.26633 (13) | 0.23096 (9) | 0.0246 (3) | |
O3 | −0.07315 (17) | 0.45398 (12) | 0.38331 (8) | 0.0202 (3) | |
N1 | 0.1130 (2) | 0.24858 (16) | 0.33886 (11) | 0.0201 (3) | |
H1 | 0.211 (3) | 0.191 (2) | 0.3536 (15) | 0.028 (6)* | |
N2 | 0.1595 (2) | 0.31515 (16) | 0.49372 (11) | 0.0217 (3) | |
H2 | 0.142 (3) | 0.379 (2) | 0.5331 (15) | 0.029 (5)* | |
N3 | 0.3205 (2) | 0.19704 (15) | 0.50985 (10) | 0.0204 (3) | |
C1 | 0.2010 (3) | 0.72212 (19) | 0.05164 (12) | 0.0195 (3) | |
C2 | 0.3549 (3) | 0.6050 (2) | 0.07675 (13) | 0.0225 (4) | |
H2A | 0.4972 | 0.6205 | 0.0571 | 0.027* | |
C3 | 0.3030 (3) | 0.46608 (19) | 0.13018 (13) | 0.0219 (4) | |
H3 | 0.4083 | 0.3888 | 0.1461 | 0.026* | |
C4 | 0.0908 (2) | 0.44445 (18) | 0.15951 (12) | 0.0170 (3) | |
C5 | −0.0663 (3) | 0.55888 (19) | 0.13637 (13) | 0.0215 (4) | |
H5 | −0.2081 | 0.5436 | 0.1572 | 0.026* | |
C6 | −0.0105 (3) | 0.69659 (19) | 0.08185 (13) | 0.0226 (4) | |
H6 | −0.1165 | 0.7733 | 0.0652 | 0.027* | |
C7 | 0.2622 (3) | 0.8732 (2) | −0.00399 (13) | 0.0265 (4) | |
H7A | 0.4033 | 0.8640 | −0.0344 | 0.040* | |
H7B | 0.2607 | 0.9415 | 0.0432 | 0.040* | |
H7C | 0.1616 | 0.9108 | −0.0564 | 0.040* | |
C8 | 0.0581 (2) | 0.34786 (18) | 0.40502 (12) | 0.0179 (3) | |
C9 | 0.5333 (3) | 0.2569 (2) | 0.51079 (13) | 0.0243 (4) | |
H9AA | 0.5465 | 0.3355 | 0.4512 | 0.029* | 0.927 (5) |
H9AB | 0.6401 | 0.1770 | 0.5023 | 0.029* | 0.927 (5) |
H9BC | 0.5146 | 0.3585 | 0.5243 | 0.029* | 0.073 (5) |
H9BD | 0.6016 | 0.2617 | 0.4436 | 0.029* | 0.073 (5) |
C10A | 0.5911 (3) | 0.3199 (2) | 0.60256 (14) | 0.0222 (5) | 0.927 (5) |
H10A | 0.4728 | 0.3864 | 0.6202 | 0.027* | 0.927 (5) |
H10B | 0.7147 | 0.3793 | 0.5846 | 0.027* | 0.927 (5) |
C10B | 0.679 (3) | 0.165 (2) | 0.5886 (6) | 0.034 (8)* | 0.073 (5) |
H10C | 0.8264 | 0.1836 | 0.5669 | 0.040* | 0.073 (5) |
H10D | 0.6599 | 0.0598 | 0.5906 | 0.040* | 0.073 (5) |
C11 | 0.6418 (3) | 0.1993 (2) | 0.69612 (13) | 0.0255 (4) | |
H11A | 0.7286 | 0.1180 | 0.6735 | 0.031* | 0.927 (5) |
H11B | 0.7281 | 0.2422 | 0.7408 | 0.031* | 0.927 (5) |
H11C | 0.6263 | 0.3075 | 0.6909 | 0.031* | 0.073 (5) |
H11D | 0.7696 | 0.1641 | 0.7342 | 0.031* | 0.073 (5) |
C12 | 0.4494 (3) | 0.1327 (2) | 0.75867 (13) | 0.0250 (4) | |
H12A | 0.4882 | 0.0282 | 0.7864 | 0.030* | |
H12B | 0.4225 | 0.1845 | 0.8160 | 0.030* | |
C13 | 0.2412 (3) | 0.13973 (19) | 0.70238 (12) | 0.0207 (4) | |
H13A | 0.1398 | 0.0795 | 0.7462 | 0.025* | |
H13B | 0.1815 | 0.2428 | 0.6904 | 0.024 (5)* | |
C14 | 0.2636 (3) | 0.0855 (2) | 0.60060 (13) | 0.0233 (4) | |
H14A | 0.371 (3) | 0.004 (2) | 0.6037 (13) | 0.022 (5)* | |
H14B | 0.129 (3) | 0.047 (2) | 0.5862 (14) | 0.025 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0234 (2) | 0.0156 (2) | 0.0170 (2) | −0.00040 (16) | −0.00456 (16) | −0.00297 (16) |
O1 | 0.0360 (7) | 0.0189 (6) | 0.0213 (6) | 0.0036 (5) | −0.0061 (5) | −0.0074 (5) |
O2 | 0.0242 (6) | 0.0219 (6) | 0.0273 (7) | −0.0048 (5) | −0.0049 (5) | −0.0012 (5) |
O3 | 0.0228 (6) | 0.0182 (6) | 0.0189 (6) | 0.0034 (5) | −0.0020 (5) | −0.0027 (5) |
N1 | 0.0253 (8) | 0.0169 (7) | 0.0173 (7) | 0.0046 (6) | −0.0058 (6) | −0.0025 (6) |
N2 | 0.0286 (8) | 0.0187 (8) | 0.0180 (7) | 0.0062 (6) | −0.0041 (6) | −0.0064 (6) |
N3 | 0.0234 (7) | 0.0185 (7) | 0.0188 (7) | 0.0037 (6) | −0.0051 (6) | −0.0030 (6) |
C1 | 0.0243 (8) | 0.0214 (9) | 0.0137 (8) | −0.0030 (7) | −0.0029 (6) | −0.0047 (7) |
C2 | 0.0170 (8) | 0.0271 (10) | 0.0239 (9) | −0.0032 (7) | 0.0018 (7) | −0.0059 (7) |
C3 | 0.0192 (8) | 0.0224 (9) | 0.0239 (9) | 0.0044 (7) | −0.0030 (7) | −0.0047 (7) |
C4 | 0.0213 (8) | 0.0169 (8) | 0.0128 (8) | 0.0002 (6) | −0.0033 (6) | −0.0029 (6) |
C5 | 0.0170 (8) | 0.0238 (9) | 0.0224 (9) | 0.0002 (7) | −0.0011 (7) | −0.0012 (7) |
C6 | 0.0217 (8) | 0.0207 (9) | 0.0233 (9) | 0.0042 (7) | −0.0025 (7) | −0.0005 (7) |
C7 | 0.0291 (9) | 0.0247 (10) | 0.0250 (9) | −0.0058 (8) | −0.0025 (7) | −0.0005 (7) |
C8 | 0.0202 (8) | 0.0158 (8) | 0.0168 (8) | −0.0032 (7) | 0.0020 (6) | −0.0004 (6) |
C9 | 0.0254 (9) | 0.0251 (9) | 0.0211 (9) | −0.0006 (7) | 0.0002 (7) | −0.0012 (7) |
C10A | 0.0191 (9) | 0.0216 (10) | 0.0264 (11) | −0.0035 (7) | 0.0013 (7) | −0.0054 (8) |
C11 | 0.0197 (8) | 0.0339 (10) | 0.0237 (9) | 0.0004 (7) | −0.0050 (7) | −0.0071 (8) |
C12 | 0.0250 (9) | 0.0303 (10) | 0.0184 (9) | 0.0030 (7) | −0.0022 (7) | −0.0027 (7) |
C13 | 0.0205 (8) | 0.0192 (9) | 0.0206 (9) | −0.0015 (7) | −0.0001 (7) | 0.0012 (7) |
C14 | 0.0282 (9) | 0.0167 (9) | 0.0253 (9) | −0.0034 (8) | −0.0060 (7) | −0.0029 (7) |
S1—O1 | 1.4291 (12) | C9—H9AA | 0.9700 |
S1—O2 | 1.4235 (12) | C9—H9AB | 0.9700 |
S1—N1 | 1.6461 (14) | C9—H9BC | 0.9700 |
S1—C4 | 1.7556 (16) | C9—H9BD | 0.9700 |
O3—C8 | 1.2222 (19) | C9—C10A | 1.509 (2) |
N1—H1 | 0.79 (2) | C9—C10B | 1.503 (6) |
N1—C8 | 1.388 (2) | C10A—H10A | 0.9700 |
N2—H2 | 0.85 (2) | C10A—H10B | 0.9700 |
N2—N3 | 1.4121 (19) | C10A—C11 | 1.529 (3) |
N2—C8 | 1.341 (2) | C10B—H10C | 0.9700 |
N3—C9 | 1.474 (2) | C10B—H10D | 0.9700 |
N3—C14 | 1.476 (2) | C10B—C11 | 1.523 (6) |
C1—C2 | 1.387 (2) | C11—H11A | 0.9700 |
C1—C6 | 1.389 (2) | C11—H11B | 0.9700 |
C1—C7 | 1.501 (2) | C11—H11C | 0.9700 |
C2—H2A | 0.9300 | C11—H11D | 0.9700 |
C2—C3 | 1.382 (2) | C11—C12 | 1.529 (2) |
C3—H3 | 0.9300 | C12—H12A | 0.9700 |
C3—C4 | 1.384 (2) | C12—H12B | 0.9700 |
C4—C5 | 1.381 (2) | C12—C13 | 1.524 (2) |
C5—H5 | 0.9300 | C13—H13A | 0.9700 |
C5—C6 | 1.384 (2) | C13—H13B | 0.9700 |
C6—H6 | 0.9300 | C13—C14 | 1.523 (2) |
C7—H7A | 0.9600 | C14—H14A | 0.958 (19) |
C7—H7B | 0.9600 | C14—H14B | 0.976 (18) |
C7—H7C | 0.9600 | ||
O1—S1—N1 | 103.40 (7) | H9AA—C9—H9AB | 107.1 |
O1—S1—C4 | 109.34 (7) | H9BC—C9—H9BD | 107.7 |
O2—S1—O1 | 119.79 (7) | C10A—C9—H9AA | 107.6 |
O2—S1—N1 | 109.04 (7) | C10A—C9—H9AB | 107.6 |
O2—S1—C4 | 108.88 (7) | C10B—C9—H9BC | 108.8 |
N1—S1—C4 | 105.40 (7) | C10B—C9—H9BD | 108.8 |
S1—N1—H1 | 118.3 (15) | C9—C10A—H10A | 108.9 |
C8—N1—S1 | 123.78 (12) | C9—C10A—H10B | 108.9 |
C8—N1—H1 | 116.7 (15) | C9—C10A—C11 | 113.52 (15) |
N3—N2—H2 | 121.7 (14) | H10A—C10A—H10B | 107.7 |
C8—N2—H2 | 116.7 (14) | C11—C10A—H10A | 108.9 |
C8—N2—N3 | 120.38 (14) | C11—C10A—H10B | 108.9 |
N2—N3—C9 | 110.62 (13) | C9—C10B—H10C | 108.7 |
N2—N3—C14 | 110.04 (13) | C9—C10B—H10D | 108.7 |
C9—N3—C14 | 115.25 (13) | C9—C10B—C11 | 114.2 (4) |
C2—C1—C6 | 118.07 (15) | H10C—C10B—H10D | 107.6 |
C2—C1—C7 | 120.93 (15) | C11—C10B—H10C | 108.7 |
C6—C1—C7 | 120.98 (15) | C11—C10B—H10D | 108.7 |
C1—C2—H2A | 119.0 | C10A—C11—H11A | 108.2 |
C3—C2—C1 | 121.91 (15) | C10A—C11—H11B | 108.2 |
C3—C2—H2A | 119.0 | C10B—C11—H11C | 107.9 |
C2—C3—H3 | 120.7 | C10B—C11—H11D | 107.9 |
C2—C3—C4 | 118.59 (16) | C10B—C11—C12 | 117.5 (10) |
C4—C3—H3 | 120.7 | H11A—C11—H11B | 107.4 |
C3—C4—S1 | 119.48 (13) | H11C—C11—H11D | 107.2 |
C5—C4—S1 | 119.48 (12) | C12—C11—C10A | 116.33 (14) |
C5—C4—C3 | 121.00 (15) | C12—C11—H11A | 108.2 |
C4—C5—H5 | 120.3 | C12—C11—H11B | 108.2 |
C4—C5—C6 | 119.32 (15) | C12—C11—H11C | 107.9 |
C6—C5—H5 | 120.3 | C12—C11—H11D | 107.9 |
C1—C6—H6 | 119.5 | C11—C12—H12A | 108.2 |
C5—C6—C1 | 121.09 (16) | C11—C12—H12B | 108.2 |
C5—C6—H6 | 119.5 | H12A—C12—H12B | 107.3 |
C1—C7—H7A | 109.5 | C13—C12—C11 | 116.50 (14) |
C1—C7—H7B | 109.5 | C13—C12—H12A | 108.2 |
C1—C7—H7C | 109.5 | C13—C12—H12B | 108.2 |
H7A—C7—H7B | 109.5 | C12—C13—H13A | 108.6 |
H7A—C7—H7C | 109.5 | C12—C13—H13B | 108.6 |
H7B—C7—H7C | 109.5 | H13A—C13—H13B | 107.5 |
O3—C8—N1 | 122.01 (15) | C14—C13—C12 | 114.83 (14) |
O3—C8—N2 | 123.97 (15) | C14—C13—H13A | 108.6 |
N2—C8—N1 | 114.02 (15) | C14—C13—H13B | 108.6 |
N3—C9—H9AA | 107.6 | N3—C14—C13 | 116.91 (14) |
N3—C9—H9AB | 107.6 | N3—C14—H14A | 106.2 (11) |
N3—C9—H9BC | 108.8 | N3—C14—H14B | 106.5 (11) |
N3—C9—H9BD | 108.8 | C13—C14—H14A | 110.4 (11) |
N3—C9—C10A | 118.75 (14) | C13—C14—H14B | 109.5 (11) |
N3—C9—C10B | 113.9 (10) | H14A—C14—H14B | 106.8 (15) |
S1—N1—C8—O3 | 3.3 (2) | C2—C3—C4—S1 | 177.74 (12) |
S1—N1—C8—N2 | −177.45 (11) | C2—C3—C4—C5 | −0.2 (2) |
S1—C4—C5—C6 | −177.06 (12) | C3—C4—C5—C6 | 0.8 (2) |
O1—S1—N1—C8 | 172.42 (13) | C4—S1—N1—C8 | 57.66 (15) |
O1—S1—C4—C3 | −38.35 (15) | C4—C5—C6—C1 | −1.1 (2) |
O1—S1—C4—C5 | 139.59 (13) | C6—C1—C2—C3 | 0.0 (2) |
O2—S1—N1—C8 | −59.09 (15) | C7—C1—C2—C3 | 178.37 (15) |
O2—S1—C4—C3 | −170.91 (12) | C7—C1—C6—C5 | −177.67 (15) |
O2—S1—C4—C5 | 7.03 (15) | C8—N2—N3—C9 | 109.40 (16) |
N1—S1—C4—C3 | 72.23 (14) | C8—N2—N3—C14 | −122.11 (15) |
N1—S1—C4—C5 | −109.83 (14) | C9—N3—C14—C13 | 64.2 (2) |
N2—N3—C9—C10A | 73.62 (19) | C9—C10A—C11—C12 | −79.85 (19) |
N2—N3—C9—C10B | 141.4 (3) | C9—C10B—C11—C12 | 77.6 (17) |
N2—N3—C14—C13 | −61.73 (19) | C10A—C11—C12—C13 | 24.9 (2) |
N3—N2—C8—O3 | −175.31 (14) | C10B—C11—C12—C13 | −42.5 (4) |
N3—N2—C8—N1 | 5.5 (2) | C11—C12—C13—C14 | 48.7 (2) |
N3—C9—C10A—C11 | 74.5 (2) | C12—C13—C14—N3 | −86.64 (19) |
N3—C9—C10B—C11 | −82.3 (16) | C14—N3—C9—C10A | −52.0 (2) |
C1—C2—C3—C4 | −0.3 (2) | C14—N3—C9—C10B | 15.8 (4) |
C2—C1—C6—C5 | 0.7 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O3i | 0.85 (2) | 2.05 (2) | 2.8961 (18) | 173.4 (19) |
Symmetry code: (i) −x, −y+1, −z+1. |
C14H21N3O3S | F(000) = 332 |
Mr = 311.40 | Dx = 1.400 Mg m−3 |
Triclinic, P1 | Melting point: 444 K |
a = 6.2433 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.0724 (4) Å | Cell parameters from 5559 reflections |
c = 13.3119 (5) Å | θ = 2.3–29.0° |
α = 79.359 (4)° | µ = 0.23 mm−1 |
β = 87.461 (3)° | T = 100 K |
γ = 85.933 (3)° | Block, colourless |
V = 738.80 (5) Å3 | 0.4 × 0.1 × 0.05 mm |
Z = 2 |
Xcalibur, Ruby, Gemini ultra diffractometer | 3021 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2604 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 26.4°, θmin = 1.6° |
ω scans | h = −7→7 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | k = −11→11 |
Tmin = 0.934, Tmax = 1.000 | l = −16→16 |
11890 measured reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.036 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.086 | w = 1/[σ2(Fo2) + (0.034P)2 + 0.3817P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
3021 reflections | Δρmax = 0.44 e Å−3 |
208 parameters | Δρmin = −0.40 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 | 0.01861 (6) | 0.26687 (4) | 0.22346 (3) | 0.01516 (12) | |
O1 | 0.14105 (19) | 0.15283 (13) | 0.18048 (9) | 0.0204 (3) | |
O2 | −0.20987 (18) | 0.26621 (13) | 0.23085 (9) | 0.0200 (3) | |
O3 | −0.07370 (17) | 0.45367 (12) | 0.38361 (8) | 0.0167 (3) | |
N1 | 0.1127 (2) | 0.24786 (16) | 0.33920 (10) | 0.0162 (3) | |
H1 | 0.213 (3) | 0.193 (2) | 0.3511 (14) | 0.019 (5)* | |
N2 | 0.1591 (2) | 0.31406 (16) | 0.49428 (11) | 0.0173 (3) | |
H2 | 0.143 (3) | 0.376 (2) | 0.5328 (15) | 0.020 (5)* | |
N3 | 0.3212 (2) | 0.19597 (15) | 0.51034 (10) | 0.0163 (3) | |
C1 | 0.2002 (3) | 0.72260 (18) | 0.05139 (12) | 0.0164 (3) | |
C2 | 0.3551 (3) | 0.60528 (19) | 0.07648 (12) | 0.0182 (4) | |
H2A | 0.4978 | 0.6208 | 0.0568 | 0.022* | |
C3 | 0.3031 (3) | 0.46589 (19) | 0.12991 (12) | 0.0183 (4) | |
H3 | 0.4086 | 0.3883 | 0.1456 | 0.022* | |
C4 | 0.0901 (2) | 0.44457 (18) | 0.15961 (11) | 0.0140 (3) | |
C5 | −0.0676 (3) | 0.55928 (19) | 0.13686 (12) | 0.0177 (4) | |
H5 | −0.2096 | 0.5441 | 0.1581 | 0.021* | |
C6 | −0.0119 (3) | 0.69707 (19) | 0.08208 (12) | 0.0184 (4) | |
H6 | −0.1182 | 0.7739 | 0.0655 | 0.022* | |
C7 | 0.2614 (3) | 0.87395 (19) | −0.00417 (13) | 0.0216 (4) | |
H7A | 0.4033 | 0.8650 | −0.0342 | 0.032* | |
H7B | 0.2588 | 0.9422 | 0.0431 | 0.032* | |
H7C | 0.1612 | 0.9114 | −0.0570 | 0.032* | |
C8 | 0.0576 (2) | 0.34693 (18) | 0.40537 (12) | 0.0145 (3) | |
C9 | 0.5343 (3) | 0.25590 (19) | 0.51034 (13) | 0.0192 (4) | |
H9A | 0.5472 | 0.3340 | 0.4503 | 0.023* | |
H9B | 0.6415 | 0.1758 | 0.5023 | 0.023* | |
C10 | 0.5917 (3) | 0.32049 (19) | 0.60253 (13) | 0.0209 (4) | |
H10A | 0.4722 | 0.3862 | 0.6202 | 0.025* | |
H10B | 0.7147 | 0.3807 | 0.5843 | 0.025* | |
C11 | 0.6442 (3) | 0.1997 (2) | 0.69586 (13) | 0.0202 (4) | |
H11A | 0.7323 | 0.2422 | 0.7401 | 0.024* | |
H11B | 0.7299 | 0.1181 | 0.6729 | 0.024* | |
C12 | 0.4515 (3) | 0.1338 (2) | 0.75942 (12) | 0.0199 (4) | |
H12A | 0.4907 | 0.0297 | 0.7883 | 0.024* | |
H12B | 0.4243 | 0.1871 | 0.8160 | 0.024* | |
C13 | 0.2424 (3) | 0.13928 (19) | 0.70317 (12) | 0.0169 (3) | |
H13A | 0.1415 | 0.0787 | 0.7473 | 0.020* | |
H13B | 0.1814 | 0.2421 | 0.6907 | 0.022 (5)* | |
C14 | 0.2657 (3) | 0.08411 (19) | 0.60146 (13) | 0.0184 (4) | |
H14A | 0.374 (3) | 0.002 (2) | 0.6061 (14) | 0.020 (5)* | |
H14B | 0.131 (3) | 0.0457 (19) | 0.5867 (13) | 0.015 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0187 (2) | 0.0129 (2) | 0.0140 (2) | −0.00021 (15) | −0.00386 (15) | −0.00245 (15) |
O1 | 0.0284 (6) | 0.0163 (6) | 0.0177 (6) | 0.0021 (5) | −0.0038 (5) | −0.0066 (5) |
O2 | 0.0189 (6) | 0.0183 (6) | 0.0226 (6) | −0.0039 (5) | −0.0036 (5) | −0.0013 (5) |
O3 | 0.0179 (6) | 0.0156 (6) | 0.0159 (6) | 0.0024 (5) | −0.0008 (4) | −0.0024 (5) |
N1 | 0.0187 (7) | 0.0148 (7) | 0.0145 (7) | 0.0041 (6) | −0.0045 (6) | −0.0024 (6) |
N2 | 0.0224 (7) | 0.0149 (7) | 0.0153 (7) | 0.0049 (6) | −0.0032 (6) | −0.0062 (6) |
N3 | 0.0177 (7) | 0.0150 (7) | 0.0157 (7) | 0.0032 (5) | −0.0037 (5) | −0.0026 (6) |
C1 | 0.0205 (8) | 0.0181 (8) | 0.0115 (8) | −0.0033 (7) | −0.0025 (6) | −0.0041 (6) |
C2 | 0.0147 (8) | 0.0217 (9) | 0.0185 (9) | −0.0024 (7) | 0.0007 (6) | −0.0045 (7) |
C3 | 0.0158 (8) | 0.0197 (9) | 0.0190 (9) | 0.0042 (7) | −0.0027 (6) | −0.0044 (7) |
C4 | 0.0184 (8) | 0.0140 (8) | 0.0101 (7) | −0.0003 (6) | −0.0020 (6) | −0.0029 (6) |
C5 | 0.0142 (8) | 0.0200 (9) | 0.0180 (8) | 0.0003 (7) | −0.0003 (6) | −0.0014 (7) |
C6 | 0.0173 (8) | 0.0167 (9) | 0.0195 (9) | 0.0046 (7) | −0.0023 (7) | −0.0007 (7) |
C7 | 0.0247 (9) | 0.0193 (9) | 0.0202 (9) | −0.0049 (7) | −0.0023 (7) | −0.0005 (7) |
C8 | 0.0152 (8) | 0.0138 (8) | 0.0140 (8) | −0.0037 (6) | 0.0025 (6) | −0.0010 (6) |
C9 | 0.0194 (8) | 0.0193 (9) | 0.0178 (8) | −0.0002 (7) | 0.0009 (7) | −0.0013 (7) |
C10 | 0.0181 (8) | 0.0210 (9) | 0.0243 (9) | −0.0029 (7) | 0.0017 (7) | −0.0060 (7) |
C11 | 0.0154 (8) | 0.0271 (10) | 0.0190 (9) | 0.0003 (7) | −0.0037 (7) | −0.0065 (7) |
C12 | 0.0201 (8) | 0.0240 (9) | 0.0147 (8) | 0.0024 (7) | −0.0014 (7) | −0.0023 (7) |
C13 | 0.0161 (8) | 0.0156 (8) | 0.0173 (8) | −0.0010 (6) | 0.0013 (6) | 0.0008 (7) |
C14 | 0.0211 (9) | 0.0143 (8) | 0.0197 (9) | −0.0019 (7) | −0.0049 (7) | −0.0013 (7) |
S1—O1 | 1.4317 (12) | C6—H6 | 0.9300 |
S1—O2 | 1.4258 (12) | C7—H7A | 0.9600 |
S1—N1 | 1.6481 (14) | C7—H7B | 0.9600 |
S1—C4 | 1.7557 (16) | C7—H7C | 0.9600 |
O3—C8 | 1.2242 (19) | C9—H9A | 0.9700 |
N1—H1 | 0.78 (2) | C9—H9B | 0.9700 |
N1—C8 | 1.387 (2) | C9—C10 | 1.521 (2) |
N2—H2 | 0.83 (2) | C10—H10A | 0.9700 |
N2—N3 | 1.4139 (19) | C10—H10B | 0.9700 |
N2—C8 | 1.342 (2) | C10—C11 | 1.528 (2) |
N3—C9 | 1.472 (2) | C11—H11A | 0.9700 |
N3—C14 | 1.476 (2) | C11—H11B | 0.9700 |
C1—C2 | 1.390 (2) | C11—C12 | 1.532 (2) |
C1—C6 | 1.391 (2) | C12—H12A | 0.9700 |
C1—C7 | 1.501 (2) | C12—H12B | 0.9700 |
C2—H2A | 0.9300 | C12—C13 | 1.526 (2) |
C2—C3 | 1.384 (2) | C13—H13A | 0.9700 |
C3—H3 | 0.9300 | C13—H13B | 0.9700 |
C3—C4 | 1.387 (2) | C13—C14 | 1.526 (2) |
C4—C5 | 1.382 (2) | C14—H14A | 0.96 (2) |
C5—H5 | 0.9300 | C14—H14B | 0.976 (17) |
C5—C6 | 1.385 (2) | ||
O1—S1—N1 | 103.36 (7) | O3—C8—N1 | 122.14 (15) |
O1—S1—C4 | 109.38 (7) | O3—C8—N2 | 123.79 (15) |
O2—S1—O1 | 119.81 (7) | N2—C8—N1 | 114.06 (14) |
O2—S1—N1 | 109.07 (7) | N3—C9—H9A | 107.7 |
O2—S1—C4 | 108.81 (7) | N3—C9—H9B | 107.7 |
N1—S1—C4 | 105.43 (7) | N3—C9—C10 | 118.26 (13) |
S1—N1—H1 | 116.4 (14) | H9A—C9—H9B | 107.1 |
C8—N1—S1 | 123.71 (12) | C10—C9—H9A | 107.7 |
C8—N1—H1 | 118.0 (14) | C10—C9—H9B | 107.7 |
N3—N2—H2 | 121.3 (13) | C9—C10—H10A | 109.0 |
C8—N2—H2 | 117.0 (14) | C9—C10—H10B | 109.0 |
C8—N2—N3 | 120.31 (14) | C9—C10—C11 | 113.05 (14) |
N2—N3—C9 | 110.70 (12) | H10A—C10—H10B | 107.8 |
N2—N3—C14 | 110.19 (12) | C11—C10—H10A | 109.0 |
C9—N3—C14 | 115.29 (13) | C11—C10—H10B | 109.0 |
C2—C1—C6 | 118.10 (15) | C10—C11—H11A | 108.3 |
C2—C1—C7 | 120.87 (14) | C10—C11—H11B | 108.3 |
C6—C1—C7 | 121.00 (15) | C10—C11—C12 | 116.08 (14) |
C1—C2—H2A | 119.1 | H11A—C11—H11B | 107.4 |
C3—C2—C1 | 121.85 (15) | C12—C11—H11A | 108.3 |
C3—C2—H2A | 119.1 | C12—C11—H11B | 108.3 |
C2—C3—H3 | 120.8 | C11—C12—H12A | 108.2 |
C2—C3—C4 | 118.50 (15) | C11—C12—H12B | 108.2 |
C4—C3—H3 | 120.8 | H12A—C12—H12B | 107.3 |
C3—C4—S1 | 119.34 (13) | C13—C12—C11 | 116.41 (14) |
C5—C4—S1 | 119.49 (12) | C13—C12—H12A | 108.2 |
C5—C4—C3 | 121.14 (15) | C13—C12—H12B | 108.2 |
C4—C5—H5 | 120.4 | C12—C13—H13A | 108.6 |
C4—C5—C6 | 119.26 (14) | C12—C13—H13B | 108.6 |
C6—C5—H5 | 120.4 | H13A—C13—H13B | 107.5 |
C1—C6—H6 | 119.4 | C14—C13—C12 | 114.79 (14) |
C5—C6—C1 | 121.14 (15) | C14—C13—H13A | 108.6 |
C5—C6—H6 | 119.4 | C14—C13—H13B | 108.6 |
C1—C7—H7A | 109.5 | N3—C14—C13 | 116.73 (13) |
C1—C7—H7B | 109.5 | N3—C14—H14A | 107.1 (11) |
C1—C7—H7C | 109.5 | N3—C14—H14B | 105.8 (10) |
H7A—C7—H7B | 109.5 | C13—C14—H14A | 109.6 (11) |
H7A—C7—H7C | 109.5 | C13—C14—H14B | 109.6 (10) |
H7B—C7—H7C | 109.5 | H14A—C14—H14B | 107.5 (14) |
S1—N1—C8—O3 | 3.1 (2) | C2—C1—C6—C5 | 0.6 (2) |
S1—N1—C8—N2 | −177.43 (11) | C2—C3—C4—S1 | 177.75 (12) |
S1—C4—C5—C6 | −176.85 (12) | C2—C3—C4—C5 | −0.1 (2) |
O1—S1—N1—C8 | 172.36 (13) | C3—C4—C5—C6 | 1.0 (2) |
O1—S1—C4—C3 | −38.04 (15) | C4—S1—N1—C8 | 57.57 (14) |
O1—S1—C4—C5 | 139.86 (13) | C4—C5—C6—C1 | −1.2 (2) |
O2—S1—N1—C8 | −59.12 (14) | C6—C1—C2—C3 | 0.4 (2) |
O2—S1—C4—C3 | −170.60 (12) | C7—C1—C2—C3 | 178.37 (15) |
O2—S1—C4—C5 | 7.29 (15) | C7—C1—C6—C5 | −177.44 (15) |
N1—S1—C4—C3 | 72.53 (14) | C8—N2—N3—C9 | 108.76 (16) |
N1—S1—C4—C5 | −109.58 (13) | C8—N2—N3—C14 | −122.52 (15) |
N2—N3—C9—C10 | 73.30 (18) | C9—N3—C14—C13 | 64.96 (19) |
N2—N3—C14—C13 | −61.22 (18) | C9—C10—C11—C12 | −80.88 (18) |
N3—N2—C8—O3 | −174.91 (14) | C10—C11—C12—C13 | 26.0 (2) |
N3—N2—C8—N1 | 5.7 (2) | C11—C12—C13—C14 | 48.0 (2) |
N3—C9—C10—C11 | 75.08 (19) | C12—C13—C14—N3 | −86.73 (18) |
C1—C2—C3—C4 | −0.6 (2) | C14—N3—C9—C10 | −52.6 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O3i | 0.83 (2) | 2.07 (2) | 2.8975 (18) | 172.9 (19) |
Symmetry code: (i) −x, −y+1, −z+1. |
C14H21N3O3S | F(000) = 332 |
Mr = 311.40 | Dx = 1.325 Mg m−3 |
Triclinic, P1 | Melting point: 444 K |
a = 6.4948 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.0520 (4) Å | Cell parameters from 4126 reflections |
c = 13.4605 (6) Å | θ = 3.8–25.7° |
α = 82.467 (4)° | µ = 0.22 mm−1 |
β = 85.251 (4)° | T = 295 K |
γ = 85.836 (4)° | Plate, colourless |
V = 780.31 (6) Å3 | 0.45 × 0.3 × 0.05 mm |
Z = 2 |
Xcalibur, Ruby, Gemini ultra diffractometer | 3189 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source | 2335 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 26.4°, θmin = 3.4° |
ω scans | h = −8→8 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | k = −11→11 |
Tmin = 0.949, Tmax = 1.000 | l = −16→16 |
12592 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.044 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.116 | w = 1/[σ2(Fo2) + (0.051P)2 + 0.1546P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
3189 reflections | Δρmax = 0.20 e Å−3 |
218 parameters | Δρmin = −0.28 e Å−3 |
3 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 | 0.25229 (8) | 0.97193 (5) | 0.39243 (4) | 0.03985 (18) | |
O3 | 0.0634 (2) | 0.67313 (16) | 0.41245 (11) | 0.0514 (4) | |
N1 | 0.2532 (3) | 0.83253 (19) | 0.48202 (13) | 0.0397 (4) | |
N3 | 0.2865 (3) | 0.64152 (19) | 0.64517 (12) | 0.0415 (4) | |
O1 | 0.3453 (2) | 1.08737 (15) | 0.43255 (11) | 0.0498 (4) | |
O2 | 0.0517 (2) | 1.00085 (17) | 0.35695 (12) | 0.0524 (4) | |
C8 | 0.1568 (3) | 0.7003 (2) | 0.48233 (15) | 0.0390 (5) | |
C4 | 0.4216 (3) | 0.9122 (2) | 0.29466 (14) | 0.0393 (5) | |
N2 | 0.1798 (3) | 0.6048 (2) | 0.56578 (14) | 0.0538 (5) | |
C5 | 0.6253 (3) | 0.8690 (2) | 0.31221 (16) | 0.0445 (5) | |
H5 | 0.6713 | 0.8667 | 0.3760 | 0.053* | |
C3 | 0.3526 (4) | 0.9165 (3) | 0.19988 (16) | 0.0513 (6) | |
H3 | 0.2154 | 0.9455 | 0.1885 | 0.062* | |
C1 | 0.6949 (4) | 0.8344 (3) | 0.13806 (17) | 0.0548 (6) | |
C6 | 0.7592 (4) | 0.8295 (3) | 0.23391 (17) | 0.0525 (6) | |
H6 | 0.8958 | 0.7990 | 0.2457 | 0.063* | |
C2 | 0.4894 (4) | 0.8774 (3) | 0.12254 (16) | 0.0591 (7) | |
H2A | 0.4432 | 0.8798 | 0.0587 | 0.071* | |
C14 | 0.4723 (4) | 0.5409 (3) | 0.65574 (19) | 0.0603 (6) | |
H14A | 0.5743 | 0.5765 | 0.6030 | 0.072* | 0.474 (7) |
H14B | 0.4367 | 0.4439 | 0.6416 | 0.072* | 0.474 (7) |
H14C | 0.5478 | 0.5408 | 0.5905 | 0.072* | 0.526 (7) |
H14D | 0.4307 | 0.4403 | 0.6776 | 0.072* | 0.526 (7) |
C9 | 0.1446 (4) | 0.6451 (3) | 0.73508 (17) | 0.0577 (6) | |
H9A | 0.1303 | 0.5438 | 0.7676 | 0.069* | |
H9B | 0.0093 | 0.6849 | 0.7152 | 0.069* | |
C10 | 0.2141 (5) | 0.7372 (3) | 0.8090 (2) | 0.0790 (9) | |
H10A | 0.2599 | 0.8298 | 0.7721 | 0.095* | |
H10B | 0.0946 | 0.7627 | 0.8531 | 0.095* | |
C7 | 0.8445 (5) | 0.7908 (4) | 0.0531 (2) | 0.0848 (9) | |
H7A | 0.7964 | 0.8367 | −0.0099 | 0.127* | |
H7B | 0.8533 | 0.6842 | 0.0546 | 0.127* | |
H7C | 0.9788 | 0.8239 | 0.0608 | 0.127* | |
C11 | 0.3805 (6) | 0.6716 (5) | 0.8724 (2) | 0.1079 (13) | |
H11C | 0.3137 | 0.6308 | 0.9363 | 0.129* | 0.526 (7) |
H11D | 0.4578 | 0.7537 | 0.8858 | 0.129* | 0.526 (7) |
H11A | 0.3426 | 0.5754 | 0.9070 | 0.129* | 0.474 (7) |
H11B | 0.3989 | 0.7362 | 0.9226 | 0.129* | 0.474 (7) |
C13A | 0.5765 (13) | 0.5165 (7) | 0.7509 (5) | 0.061 (2) | 0.474 (7) |
H13A | 0.7176 | 0.4783 | 0.7362 | 0.073* | 0.474 (7) |
H13B | 0.5075 | 0.4394 | 0.7956 | 0.073* | 0.474 (7) |
C12A | 0.5835 (8) | 0.6521 (7) | 0.8073 (5) | 0.0622 (19) | 0.474 (7) |
H12A | 0.6026 | 0.7410 | 0.7596 | 0.075* | 0.474 (7) |
H12B | 0.6993 | 0.6380 | 0.8494 | 0.075* | 0.474 (7) |
C13B | 0.6125 (10) | 0.5816 (9) | 0.7281 (4) | 0.073 (2) | 0.526 (7) |
H13C | 0.6343 | 0.6872 | 0.7124 | 0.088* | 0.526 (7) |
H13D | 0.7455 | 0.5277 | 0.7175 | 0.088* | 0.526 (7) |
C12B | 0.5396 (11) | 0.5508 (7) | 0.8398 (4) | 0.099 (3) | 0.526 (7) |
H12C | 0.4787 | 0.4548 | 0.8524 | 0.119* | 0.526 (7) |
H12D | 0.6581 | 0.5457 | 0.8798 | 0.119* | 0.526 (7) |
H1 | 0.315 (3) | 0.836 (2) | 0.5303 (17) | 0.048 (7)* | |
H2 | 0.126 (4) | 0.526 (3) | 0.5721 (17) | 0.054 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0459 (3) | 0.0346 (3) | 0.0401 (3) | −0.0066 (2) | −0.0070 (2) | −0.0037 (2) |
O3 | 0.0651 (10) | 0.0462 (9) | 0.0468 (9) | −0.0152 (7) | −0.0187 (8) | −0.0051 (7) |
N1 | 0.0475 (11) | 0.0400 (10) | 0.0334 (9) | −0.0123 (8) | −0.0079 (8) | −0.0033 (8) |
N3 | 0.0452 (10) | 0.0445 (10) | 0.0364 (9) | −0.0100 (8) | −0.0082 (8) | −0.0034 (8) |
O1 | 0.0656 (10) | 0.0352 (8) | 0.0511 (9) | −0.0123 (7) | −0.0077 (7) | −0.0079 (7) |
O2 | 0.0481 (9) | 0.0511 (9) | 0.0585 (9) | 0.0006 (7) | −0.0126 (7) | −0.0050 (7) |
C8 | 0.0428 (12) | 0.0376 (11) | 0.0380 (11) | −0.0089 (9) | −0.0035 (9) | −0.0066 (9) |
C4 | 0.0482 (12) | 0.0348 (10) | 0.0361 (11) | −0.0143 (9) | −0.0052 (9) | −0.0009 (8) |
N2 | 0.0762 (14) | 0.0423 (11) | 0.0468 (11) | −0.0270 (10) | −0.0222 (10) | 0.0039 (9) |
C5 | 0.0476 (13) | 0.0494 (12) | 0.0386 (11) | −0.0118 (10) | −0.0056 (9) | −0.0063 (10) |
C3 | 0.0544 (14) | 0.0590 (14) | 0.0413 (12) | −0.0121 (11) | −0.0106 (10) | −0.0005 (11) |
C1 | 0.0640 (16) | 0.0559 (14) | 0.0453 (13) | −0.0211 (12) | 0.0087 (11) | −0.0083 (11) |
C6 | 0.0481 (14) | 0.0561 (14) | 0.0551 (14) | −0.0114 (11) | −0.0010 (11) | −0.0107 (11) |
C2 | 0.0739 (18) | 0.0721 (16) | 0.0335 (12) | −0.0182 (14) | −0.0054 (11) | −0.0065 (11) |
C14 | 0.0594 (15) | 0.0566 (14) | 0.0660 (16) | 0.0037 (12) | −0.0081 (12) | −0.0145 (12) |
C9 | 0.0477 (14) | 0.0713 (16) | 0.0505 (14) | −0.0030 (12) | −0.0005 (11) | 0.0032 (12) |
C10 | 0.101 (2) | 0.0784 (19) | 0.0587 (16) | 0.0002 (17) | 0.0091 (16) | −0.0268 (15) |
C7 | 0.092 (2) | 0.105 (2) | 0.0595 (17) | −0.0225 (18) | 0.0209 (16) | −0.0256 (16) |
C11 | 0.117 (3) | 0.150 (4) | 0.068 (2) | −0.014 (3) | −0.024 (2) | −0.041 (2) |
C13A | 0.058 (4) | 0.049 (4) | 0.074 (5) | 0.002 (3) | −0.018 (3) | −0.001 (3) |
C12A | 0.064 (4) | 0.070 (4) | 0.058 (4) | −0.012 (3) | −0.014 (3) | −0.017 (3) |
C13B | 0.053 (4) | 0.061 (5) | 0.107 (5) | −0.008 (3) | −0.031 (4) | 0.005 (4) |
C12B | 0.150 (7) | 0.072 (5) | 0.079 (5) | −0.004 (5) | −0.060 (5) | 0.005 (4) |
S1—N1 | 1.6272 (18) | C14—C13A | 1.481 (5) |
S1—O1 | 1.4291 (14) | C14—C13B | 1.484 (5) |
S1—O2 | 1.4197 (15) | C9—H9A | 0.9700 |
S1—C4 | 1.759 (2) | C9—H9B | 0.9700 |
O3—C8 | 1.221 (2) | C9—C10 | 1.495 (4) |
N1—C8 | 1.390 (2) | C10—H10A | 0.9700 |
N1—H1 | 0.79 (2) | C10—H10B | 0.9700 |
N3—N2 | 1.408 (2) | C10—C11 | 1.475 (5) |
N3—C14 | 1.463 (3) | C7—H7A | 0.9600 |
N3—C9 | 1.462 (3) | C7—H7B | 0.9600 |
C8—N2 | 1.336 (3) | C7—H7C | 0.9600 |
C4—C5 | 1.382 (3) | C11—H11C | 0.9700 |
C4—C3 | 1.382 (3) | C11—H11D | 0.9700 |
N2—H2 | 0.81 (2) | C11—H11A | 0.9700 |
C5—H5 | 0.9300 | C11—H11B | 0.9700 |
C5—C6 | 1.377 (3) | C11—C12A | 1.535 (6) |
C3—H3 | 0.9300 | C11—C12B | 1.531 (6) |
C3—C2 | 1.377 (3) | C13A—H13A | 0.9700 |
C1—C6 | 1.383 (3) | C13A—H13B | 0.9700 |
C1—C2 | 1.388 (3) | C13A—C12A | 1.531 (5) |
C1—C7 | 1.512 (3) | C12A—H12A | 0.9700 |
C6—H6 | 0.9300 | C12A—H12B | 0.9700 |
C2—H2A | 0.9300 | C13B—H13C | 0.9700 |
C14—H14A | 0.9700 | C13B—H13D | 0.9700 |
C14—H14B | 0.9700 | C13B—C12B | 1.535 (6) |
C14—H14C | 0.9700 | C12B—H12C | 0.9700 |
C14—H14D | 0.9700 | C12B—H12D | 0.9700 |
N1—S1—C4 | 105.36 (9) | H9A—C9—H9B | 107.7 |
O1—S1—N1 | 104.51 (9) | C10—C9—H9A | 108.9 |
O1—S1—C4 | 108.23 (9) | C10—C9—H9B | 108.9 |
O2—S1—N1 | 110.37 (9) | C9—C10—H10A | 107.9 |
O2—S1—O1 | 119.15 (9) | C9—C10—H10B | 107.9 |
O2—S1—C4 | 108.37 (10) | H10A—C10—H10B | 107.2 |
S1—N1—H1 | 120.1 (16) | C11—C10—C9 | 117.7 (3) |
C8—N1—S1 | 125.60 (15) | C11—C10—H10A | 107.9 |
C8—N1—H1 | 114.3 (16) | C11—C10—H10B | 107.9 |
N2—N3—C14 | 108.75 (17) | C1—C7—H7A | 109.5 |
N2—N3—C9 | 109.58 (16) | C1—C7—H7B | 109.5 |
C9—N3—C14 | 116.07 (18) | C1—C7—H7C | 109.5 |
O3—C8—N1 | 123.25 (19) | H7A—C7—H7B | 109.5 |
O3—C8—N2 | 123.34 (18) | H7A—C7—H7C | 109.5 |
N2—C8—N1 | 113.39 (18) | H7B—C7—H7C | 109.5 |
C5—C4—S1 | 119.58 (15) | C10—C11—H11C | 106.8 |
C3—C4—S1 | 119.63 (18) | C10—C11—H11D | 106.8 |
C3—C4—C5 | 120.7 (2) | C10—C11—H11A | 109.7 |
N3—N2—H2 | 119.1 (17) | C10—C11—H11B | 109.7 |
C8—N2—N3 | 121.47 (17) | C10—C11—C12A | 110.0 (3) |
C8—N2—H2 | 119.3 (17) | C10—C11—C12B | 122.3 (3) |
C4—C5—H5 | 120.4 | H11C—C11—H11D | 106.6 |
C6—C5—C4 | 119.1 (2) | H11A—C11—H11B | 108.2 |
C6—C5—H5 | 120.4 | C12A—C11—H11A | 109.7 |
C4—C3—H3 | 120.4 | C12A—C11—H11B | 109.7 |
C2—C3—C4 | 119.2 (2) | C12B—C11—H11C | 106.8 |
C2—C3—H3 | 120.4 | C12B—C11—H11D | 106.8 |
C6—C1—C2 | 118.3 (2) | C14—C13A—H13A | 108.1 |
C6—C1—C7 | 120.6 (2) | C14—C13A—H13B | 108.1 |
C2—C1—C7 | 121.1 (2) | C14—C13A—C12A | 116.8 (4) |
C5—C6—C1 | 121.4 (2) | H13A—C13A—H13B | 107.3 |
C5—C6—H6 | 119.3 | C12A—C13A—H13A | 108.1 |
C1—C6—H6 | 119.3 | C12A—C13A—H13B | 108.1 |
C3—C2—C1 | 121.2 (2) | C11—C12A—H12A | 109.8 |
C3—C2—H2A | 119.4 | C11—C12A—H12B | 109.8 |
C1—C2—H2A | 119.4 | C13A—C12A—C11 | 109.5 (5) |
N3—C14—H14A | 107.1 | C13A—C12A—H12A | 109.8 |
N3—C14—H14B | 107.1 | C13A—C12A—H12B | 109.8 |
N3—C14—H14C | 108.8 | H12A—C12A—H12B | 108.2 |
N3—C14—H14D | 108.8 | C14—C13B—H13C | 108.2 |
N3—C14—C13A | 120.9 (3) | C14—C13B—H13D | 108.2 |
N3—C14—C13B | 113.7 (4) | C14—C13B—C12B | 116.3 (5) |
H14A—C14—H14B | 106.8 | H13C—C13B—H13D | 107.4 |
H14C—C14—H14D | 107.7 | C12B—C13B—H13C | 108.2 |
C13A—C14—H14A | 107.1 | C12B—C13B—H13D | 108.2 |
C13A—C14—H14B | 107.1 | C11—C12B—C13B | 112.1 (5) |
C13B—C14—H14C | 108.8 | C11—C12B—H12C | 109.2 |
C13B—C14—H14D | 108.8 | C11—C12B—H12D | 109.2 |
N3—C9—H9A | 108.9 | C13B—C12B—H12C | 109.2 |
N3—C9—H9B | 108.9 | C13B—C12B—H12D | 109.2 |
N3—C9—C10 | 113.3 (2) | H12C—C12B—H12D | 107.9 |
S1—N1—C8—O3 | 1.9 (3) | N2—N3—C14—C13A | −159.2 (4) |
S1—N1—C8—N2 | −179.31 (16) | N2—N3—C14—C13B | 172.2 (3) |
S1—C4—C5—C6 | −176.81 (16) | N2—N3—C9—C10 | −157.6 (2) |
S1—C4—C3—C2 | 176.45 (17) | C5—C4—C3—C2 | −0.1 (3) |
O3—C8—N2—N3 | −179.2 (2) | C3—C4—C5—C6 | −0.3 (3) |
N1—S1—C4—C5 | −58.35 (17) | C6—C1—C2—C3 | 0.9 (3) |
N1—S1—C4—C3 | 125.08 (17) | C2—C1—C6—C5 | −1.3 (3) |
N1—C8—N2—N3 | 2.1 (3) | C14—N3—N2—C8 | −115.4 (2) |
N3—C14—C13A—C12A | −37.4 (8) | C14—N3—C9—C10 | 78.7 (3) |
N3—C14—C13B—C12B | 73.0 (7) | C14—C13A—C12A—C11 | 83.8 (8) |
N3—C9—C10—C11 | −77.3 (3) | C14—C13B—C12B—C11 | −79.8 (9) |
O1—S1—N1—C8 | 172.19 (17) | C9—N3—N2—C8 | 116.8 (2) |
O1—S1—C4—C5 | 52.99 (18) | C9—N3—C14—C13A | −35.1 (5) |
O1—S1—C4—C3 | −123.58 (17) | C9—N3—C14—C13B | −63.7 (4) |
O2—S1—N1—C8 | 42.9 (2) | C9—C10—C11—C12A | 66.6 (4) |
O2—S1—C4—C5 | −176.49 (15) | C9—C10—C11—C12B | 25.6 (6) |
O2—S1—C4—C3 | 6.94 (19) | C10—C11—C12A—C13A | −76.4 (5) |
C4—S1—N1—C8 | −73.84 (19) | C10—C11—C12B—C13B | 40.8 (8) |
C4—C5—C6—C1 | 1.0 (3) | C7—C1—C6—C5 | 179.9 (2) |
C4—C3—C2—C1 | −0.3 (3) | C7—C1—C2—C3 | 179.7 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.79 (2) | 2.47 (2) | 3.105 (2) | 138 (2) |
N2—H2···O3ii | 0.81 (2) | 2.23 (2) | 3.036 (2) | 172 (2) |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x, −y+1, −z+1. |
C14H21N3O3S | F(000) = 332 |
Mr = 311.40 | Dx = 1.339 Mg m−3 |
Triclinic, P1 | Melting point: 444 K |
a = 6.4468 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.0141 (5) Å | Cell parameters from 3177 reflections |
c = 13.4850 (7) Å | θ = 3.4–24.7° |
α = 82.360 (4)° | µ = 0.22 mm−1 |
β = 85.368 (4)° | T = 250 K |
γ = 85.553 (4)° | Plate, colourless |
V = 772.38 (7) Å3 | 0.45 × 0.3 × 0.05 mm |
Z = 2 |
Xcalibur, Ruby, Gemini ultra diffractometer | 3154 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source | 2336 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.058 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 26.4°, θmin = 3.4° |
ω scans | h = −8→8 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | k = −11→11 |
Tmin = 0.837, Tmax = 1.000 | l = −16→16 |
11517 measured reflections |
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)] = 0.048 | w = 1/[σ2(Fo2) + (0.0565P)2 + 0.0711P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.122 | (Δ/σ)max < 0.001 |
S = 1.07 | Δρmax = 0.23 e Å−3 |
3154 reflections | Δρmin = −0.41 e Å−3 |
219 parameters | Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
3 restraints | Extinction coefficient: 0.181 (10) |
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 | Occ. (<1) | |
S1 | 0.25134 (8) | 0.97358 (6) | 0.39261 (4) | 0.0295 (2) | |
O3 | 0.0624 (2) | 0.67355 (17) | 0.41274 (11) | 0.0394 (4) | |
N1 | 0.2531 (3) | 0.8333 (2) | 0.48198 (14) | 0.0302 (4) | |
N3 | 0.2886 (3) | 0.6404 (2) | 0.64546 (13) | 0.0316 (4) | |
O1 | 0.3450 (2) | 1.08930 (16) | 0.43256 (12) | 0.0383 (4) | |
O2 | 0.0484 (2) | 1.00303 (17) | 0.35714 (12) | 0.0401 (4) | |
C8 | 0.1571 (3) | 0.7008 (2) | 0.48266 (16) | 0.0295 (5) | |
C4 | 0.4212 (3) | 0.9133 (2) | 0.29460 (15) | 0.0293 (5) | |
N2 | 0.1811 (3) | 0.6040 (2) | 0.56577 (14) | 0.0418 (5) | |
C5 | 0.6261 (3) | 0.8678 (2) | 0.31261 (17) | 0.0343 (5) | |
H5 | 0.6725 | 0.8641 | 0.3765 | 0.041* | |
C3 | 0.3512 (4) | 0.9198 (3) | 0.20008 (17) | 0.0384 (6) | |
H3 | 0.2132 | 0.9507 | 0.1886 | 0.046* | |
C1 | 0.6953 (4) | 0.8345 (3) | 0.13850 (17) | 0.0409 (6) | |
C6 | 0.7603 (4) | 0.8280 (3) | 0.23401 (18) | 0.0400 (6) | |
H6 | 0.8978 | 0.7961 | 0.2458 | 0.048* | |
C2 | 0.4885 (4) | 0.8797 (3) | 0.12263 (18) | 0.0456 (6) | |
H2A | 0.4418 | 0.8831 | 0.0588 | 0.055* | |
C14 | 0.4793 (4) | 0.5401 (3) | 0.6543 (2) | 0.0460 (6) | |
H14A | 0.5827 | 0.5795 | 0.6034 | 0.055* | 0.569 (7) |
H14B | 0.4476 | 0.4432 | 0.6378 | 0.055* | 0.569 (7) |
H14C | 0.5578 | 0.5453 | 0.5896 | 0.055* | 0.431 (7) |
H14D | 0.4411 | 0.4377 | 0.6731 | 0.055* | 0.431 (7) |
C9 | 0.1459 (4) | 0.6421 (3) | 0.73549 (18) | 0.0445 (6) | |
H9A | 0.1364 | 0.5403 | 0.7686 | 0.053* | |
H9B | 0.0080 | 0.6793 | 0.7159 | 0.053* | |
C10 | 0.2144 (5) | 0.7380 (3) | 0.8082 (2) | 0.0595 (8) | |
H10A | 0.2589 | 0.8306 | 0.7702 | 0.071* | |
H10B | 0.0936 | 0.7641 | 0.8517 | 0.071* | |
C7 | 0.8445 (5) | 0.7890 (4) | 0.0540 (2) | 0.0659 (9) | |
H7A | 0.8042 | 0.8434 | −0.0084 | 0.099* | |
H7B | 0.8408 | 0.6833 | 0.0515 | 0.099* | |
H7C | 0.9832 | 0.8113 | 0.0652 | 0.099* | |
C11 | 0.3837 (5) | 0.6742 (5) | 0.8724 (2) | 0.0808 (11) | |
H11C | 0.3182 | 0.6378 | 0.9375 | 0.097* | 0.431 (7) |
H11D | 0.4648 | 0.7566 | 0.8823 | 0.097* | 0.431 (7) |
H11A | 0.3449 | 0.5795 | 0.9095 | 0.097* | 0.569 (7) |
H11B | 0.4035 | 0.7421 | 0.9204 | 0.097* | 0.569 (7) |
C13A | 0.5791 (10) | 0.5139 (5) | 0.7522 (4) | 0.0450 (16) | 0.569 (7) |
H13A | 0.7204 | 0.4717 | 0.7400 | 0.054* | 0.569 (7) |
H13B | 0.5042 | 0.4387 | 0.7962 | 0.054* | 0.569 (7) |
C12A | 0.5889 (6) | 0.6491 (6) | 0.8081 (4) | 0.0489 (16) | 0.569 (7) |
H12A | 0.6120 | 0.7377 | 0.7603 | 0.059* | 0.569 (7) |
H12B | 0.7047 | 0.6326 | 0.8509 | 0.059* | 0.569 (7) |
C13B | 0.6147 (11) | 0.5805 (10) | 0.7306 (4) | 0.055 (2) | 0.431 (7) |
H13C | 0.6345 | 0.6870 | 0.7162 | 0.066* | 0.431 (7) |
H13D | 0.7505 | 0.5278 | 0.7213 | 0.066* | 0.431 (7) |
C12B | 0.5390 (12) | 0.5476 (7) | 0.8409 (5) | 0.077 (3) | 0.431 (7) |
H12C | 0.6574 | 0.5375 | 0.8820 | 0.092* | 0.431 (7) |
H12D | 0.4721 | 0.4535 | 0.8519 | 0.092* | 0.431 (7) |
H1 | 0.311 (3) | 0.838 (2) | 0.5275 (17) | 0.025 (6)* | |
H2 | 0.124 (4) | 0.527 (3) | 0.5730 (19) | 0.044 (7)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0345 (3) | 0.0254 (3) | 0.0295 (3) | −0.0047 (2) | −0.0048 (2) | −0.0032 (2) |
O3 | 0.0494 (10) | 0.0357 (9) | 0.0363 (9) | −0.0122 (8) | −0.0140 (8) | −0.0049 (7) |
N1 | 0.0364 (10) | 0.0323 (10) | 0.0237 (10) | −0.0109 (8) | −0.0058 (8) | −0.0033 (8) |
N3 | 0.0344 (10) | 0.0352 (10) | 0.0267 (10) | −0.0092 (8) | −0.0059 (8) | −0.0034 (8) |
O1 | 0.0512 (9) | 0.0266 (8) | 0.0393 (9) | −0.0096 (7) | −0.0065 (7) | −0.0060 (7) |
O2 | 0.0367 (9) | 0.0388 (9) | 0.0451 (10) | 0.0021 (7) | −0.0106 (7) | −0.0042 (7) |
C8 | 0.0318 (11) | 0.0283 (11) | 0.0296 (12) | −0.0060 (9) | −0.0020 (9) | −0.0057 (9) |
C4 | 0.0355 (11) | 0.0267 (11) | 0.0258 (11) | −0.0089 (9) | −0.0038 (9) | 0.0008 (9) |
N2 | 0.0599 (13) | 0.0319 (11) | 0.0371 (12) | −0.0222 (10) | −0.0168 (10) | 0.0023 (9) |
C5 | 0.0376 (12) | 0.0373 (12) | 0.0295 (12) | −0.0103 (10) | −0.0033 (10) | −0.0044 (10) |
C3 | 0.0402 (13) | 0.0433 (14) | 0.0320 (13) | −0.0095 (11) | −0.0075 (10) | 0.0006 (10) |
C1 | 0.0489 (14) | 0.0399 (14) | 0.0346 (13) | −0.0146 (12) | 0.0058 (11) | −0.0053 (10) |
C6 | 0.0349 (12) | 0.0430 (14) | 0.0432 (14) | −0.0085 (11) | 0.0005 (10) | −0.0080 (11) |
C2 | 0.0597 (16) | 0.0534 (16) | 0.0251 (12) | −0.0133 (13) | −0.0051 (11) | −0.0037 (11) |
C14 | 0.0464 (14) | 0.0416 (14) | 0.0515 (16) | 0.0026 (12) | −0.0075 (12) | −0.0120 (12) |
C9 | 0.0367 (13) | 0.0562 (16) | 0.0378 (14) | −0.0034 (12) | 0.0006 (10) | 0.0026 (12) |
C10 | 0.0760 (19) | 0.0582 (18) | 0.0440 (16) | −0.0001 (15) | 0.0111 (14) | −0.0172 (14) |
C7 | 0.0738 (19) | 0.079 (2) | 0.0450 (17) | −0.0130 (17) | 0.0166 (15) | −0.0174 (15) |
C11 | 0.088 (2) | 0.111 (3) | 0.052 (2) | −0.008 (2) | −0.0177 (17) | −0.033 (2) |
C13A | 0.043 (3) | 0.035 (3) | 0.057 (4) | −0.001 (3) | −0.014 (3) | 0.000 (2) |
C12A | 0.046 (3) | 0.056 (4) | 0.049 (3) | −0.007 (2) | −0.010 (2) | −0.016 (3) |
C13B | 0.036 (4) | 0.041 (5) | 0.085 (6) | −0.003 (4) | −0.025 (4) | 0.010 (4) |
C12B | 0.119 (7) | 0.051 (5) | 0.063 (5) | −0.002 (5) | −0.052 (5) | 0.005 (4) |
S1—N1 | 1.6266 (19) | C14—C13A | 1.498 (4) |
S1—O1 | 1.4290 (14) | C14—C13B | 1.499 (5) |
S1—O2 | 1.4226 (16) | C9—H9A | 0.9700 |
S1—C4 | 1.762 (2) | C9—H9B | 0.9700 |
O3—C8 | 1.224 (2) | C9—C10 | 1.502 (4) |
N1—C8 | 1.386 (3) | C10—H10A | 0.9700 |
N1—H1 | 0.75 (2) | C10—H10B | 0.9700 |
N3—N2 | 1.411 (2) | C10—C11 | 1.482 (5) |
N3—C14 | 1.472 (3) | C7—H7A | 0.9600 |
N3—C9 | 1.464 (3) | C7—H7B | 0.9600 |
C8—N2 | 1.337 (3) | C7—H7C | 0.9600 |
C4—C5 | 1.383 (3) | C11—H11C | 0.9700 |
C4—C3 | 1.379 (3) | C11—H11D | 0.9700 |
N2—H2 | 0.80 (3) | C11—H11A | 0.9700 |
C5—H5 | 0.9300 | C11—H11B | 0.9700 |
C5—C6 | 1.381 (3) | C11—C12A | 1.541 (5) |
C3—H3 | 0.9300 | C11—C12B | 1.539 (6) |
C3—C2 | 1.381 (3) | C13A—H13A | 0.9700 |
C1—C6 | 1.379 (3) | C13A—H13B | 0.9700 |
C1—C2 | 1.389 (3) | C13A—C12A | 1.524 (5) |
C1—C7 | 1.509 (3) | C12A—H12A | 0.9700 |
C6—H6 | 0.9300 | C12A—H12B | 0.9700 |
C2—H2A | 0.9300 | C13B—H13C | 0.9700 |
C14—H14A | 0.9700 | C13B—H13D | 0.9700 |
C14—H14B | 0.9700 | C13B—C12B | 1.526 (6) |
C14—H14C | 0.9700 | C12B—H12C | 0.9700 |
C14—H14D | 0.9700 | C12B—H12D | 0.9700 |
N1—S1—C4 | 105.39 (10) | H9A—C9—H9B | 107.8 |
O1—S1—N1 | 104.58 (9) | C10—C9—H9A | 109.1 |
O1—S1—C4 | 108.36 (9) | C10—C9—H9B | 109.1 |
O2—S1—N1 | 110.32 (9) | C9—C10—H10A | 107.9 |
O2—S1—O1 | 119.18 (10) | C9—C10—H10B | 107.9 |
O2—S1—C4 | 108.16 (10) | H10A—C10—H10B | 107.2 |
S1—N1—H1 | 118.9 (17) | C11—C10—C9 | 117.5 (3) |
C8—N1—S1 | 125.85 (16) | C11—C10—H10A | 107.9 |
C8—N1—H1 | 115.2 (17) | C11—C10—H10B | 107.9 |
N2—N3—C14 | 108.44 (18) | C1—C7—H7A | 109.5 |
N2—N3—C9 | 109.61 (16) | C1—C7—H7B | 109.5 |
C9—N3—C14 | 116.68 (19) | C1—C7—H7C | 109.5 |
O3—C8—N1 | 123.1 (2) | H7A—C7—H7B | 109.5 |
O3—C8—N2 | 123.05 (18) | H7A—C7—H7C | 109.5 |
N2—C8—N1 | 113.84 (18) | H7B—C7—H7C | 109.5 |
C5—C4—S1 | 119.29 (16) | C10—C11—H11C | 107.1 |
C3—C4—S1 | 119.61 (18) | C10—C11—H11D | 107.1 |
C3—C4—C5 | 121.0 (2) | C10—C11—H11A | 109.5 |
N3—N2—H2 | 119.0 (18) | C10—C11—H11B | 109.5 |
C8—N2—N3 | 121.39 (18) | C10—C11—C12A | 110.5 (3) |
C8—N2—H2 | 119.4 (18) | C10—C11—C12B | 121.0 (3) |
C4—C5—H5 | 120.6 | H11C—C11—H11D | 106.8 |
C6—C5—C4 | 118.8 (2) | H11A—C11—H11B | 108.1 |
C6—C5—H5 | 120.6 | C12A—C11—H11A | 109.5 |
C4—C3—H3 | 120.4 | C12A—C11—H11B | 109.5 |
C4—C3—C2 | 119.2 (2) | C12B—C11—H11C | 107.1 |
C2—C3—H3 | 120.4 | C12B—C11—H11D | 107.1 |
C6—C1—C2 | 118.5 (2) | C14—C13A—H13A | 108.0 |
C6—C1—C7 | 120.6 (2) | C14—C13A—H13B | 108.0 |
C2—C1—C7 | 120.9 (2) | C14—C13A—C12A | 117.2 (4) |
C5—C6—H6 | 119.2 | H13A—C13A—H13B | 107.2 |
C1—C6—C5 | 121.6 (2) | C12A—C13A—H13A | 108.0 |
C1—C6—H6 | 119.2 | C12A—C13A—H13B | 108.0 |
C3—C2—C1 | 121.0 (2) | C11—C12A—H12A | 109.6 |
C3—C2—H2A | 119.5 | C11—C12A—H12B | 109.6 |
C1—C2—H2A | 119.5 | C13A—C12A—C11 | 110.1 (4) |
N3—C14—H14A | 107.6 | C13A—C12A—H12A | 109.6 |
N3—C14—H14B | 107.6 | C13A—C12A—H12B | 109.6 |
N3—C14—H14C | 109.2 | H12A—C12A—H12B | 108.1 |
N3—C14—H14D | 109.2 | C14—C13B—H13C | 107.9 |
N3—C14—C13A | 119.1 (3) | C14—C13B—H13D | 107.9 |
N3—C14—C13B | 112.2 (4) | C14—C13B—C12B | 117.6 (5) |
H14A—C14—H14B | 107.0 | H13C—C13B—H13D | 107.2 |
H14C—C14—H14D | 107.9 | C12B—C13B—H13C | 107.9 |
C13A—C14—H14A | 107.6 | C12B—C13B—H13D | 107.9 |
C13A—C14—H14B | 107.6 | C11—C12B—H12C | 109.5 |
C13B—C14—H14C | 109.2 | C11—C12B—H12D | 109.5 |
C13B—C14—H14D | 109.2 | C13B—C12B—C11 | 110.8 (6) |
N3—C9—H9A | 109.1 | C13B—C12B—H12C | 109.5 |
N3—C9—H9B | 109.1 | C13B—C12B—H12D | 109.5 |
N3—C9—C10 | 112.70 (19) | H12C—C12B—H12D | 108.1 |
S1—N1—C8—O3 | 1.9 (3) | N2—N3—C14—C13A | −157.5 (3) |
S1—N1—C8—N2 | −179.47 (17) | N2—N3—C14—C13B | 174.3 (3) |
S1—C4—C5—C6 | −176.80 (16) | N2—N3—C9—C10 | −156.1 (2) |
S1—C4—C3—C2 | 176.63 (17) | C5—C4—C3—C2 | 0.1 (3) |
O3—C8—N2—N3 | −179.0 (2) | C3—C4—C5—C6 | −0.3 (3) |
N1—S1—C4—C5 | −57.69 (18) | C6—C1—C2—C3 | 1.0 (3) |
N1—S1—C4—C3 | 125.74 (17) | C2—C1—C6—C5 | −1.2 (3) |
N1—C8—N2—N3 | 2.3 (3) | C14—N3—N2—C8 | −114.4 (2) |
N3—C14—C13A—C12A | −41.1 (6) | C14—N3—C9—C10 | 80.2 (3) |
N3—C14—C13B—C12B | 71.6 (7) | C14—C13A—C12A—C11 | 84.9 (6) |
N3—C9—C10—C11 | −78.5 (3) | C14—C13B—C12B—C11 | −83.1 (9) |
O1—S1—N1—C8 | 172.25 (18) | C9—N3—N2—C8 | 117.2 (2) |
O1—S1—C4—C5 | 53.81 (18) | C9—N3—C14—C13A | −33.2 (4) |
O1—S1—C4—C3 | −122.77 (17) | C9—N3—C14—C13B | −61.4 (4) |
O2—S1—N1—C8 | 42.9 (2) | C9—C10—C11—C12A | 65.1 (4) |
O2—S1—C4—C5 | −175.68 (15) | C9—C10—C11—C12B | 23.2 (6) |
O2—S1—C4—C3 | 7.7 (2) | C10—C11—C12A—C13A | −74.0 (5) |
C4—S1—N1—C8 | −73.6 (2) | C10—C11—C12B—C13B | 44.8 (7) |
C4—C5—C6—C1 | 0.8 (3) | C7—C1—C6—C5 | −179.4 (2) |
C4—C3—C2—C1 | −0.5 (3) | C7—C1—C2—C3 | 179.2 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.75 (2) | 2.48 (2) | 3.083 (2) | 139 (2) |
N2—H2···O3ii | 0.80 (3) | 2.22 (3) | 3.025 (2) | 174 (3) |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x, −y+1, −z+1. |
C14H21N3O3S | F(000) = 332 |
Mr = 311.40 | Dx = 1.352 Mg m−3 |
Triclinic, P1 | Melting point: 444 K |
a = 6.3939 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.9809 (4) Å | Cell parameters from 3525 reflections |
c = 13.5213 (7) Å | θ = 3.5–28.1° |
α = 82.129 (4)° | µ = 0.23 mm−1 |
β = 85.602 (4)° | T = 200 K |
γ = 85.341 (4)° | Plate, colourless |
V = 764.89 (6) Å3 | 0.45 × 0.3 × 0.05 mm |
Z = 2 |
Xcalibur, Ruby, Gemini ultra diffractometer | 3115 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source | 2445 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.055 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 26.4°, θmin = 3.5° |
ω scans | h = −7→7 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | k = −11→11 |
Tmin = 0.805, Tmax = 1.000 | l = −16→16 |
11396 measured reflections |
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)] = 0.045 | w = 1/[σ2(Fo2) + (0.051P)2 + 0.2748P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.113 | (Δ/σ)max < 0.001 |
S = 1.06 | Δρmax = 0.31 e Å−3 |
3115 reflections | Δρmin = −0.39 e Å−3 |
219 parameters | Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
3 restraints | Extinction coefficient: 0.204 (10) |
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 | Occ. (<1) | |
S1 | 0.25003 (8) | 0.97551 (5) | 0.39271 (4) | 0.02195 (18) | |
O3 | 0.0614 (2) | 0.67424 (16) | 0.41253 (11) | 0.0293 (4) | |
N1 | 0.2539 (3) | 0.83399 (19) | 0.48239 (13) | 0.0230 (4) | |
N3 | 0.2901 (3) | 0.63872 (19) | 0.64548 (12) | 0.0239 (4) | |
O1 | 0.3451 (2) | 1.09162 (15) | 0.43245 (11) | 0.0284 (4) | |
O2 | 0.0444 (2) | 1.00584 (16) | 0.35743 (11) | 0.0298 (4) | |
C8 | 0.1571 (3) | 0.7010 (2) | 0.48257 (15) | 0.0230 (4) | |
C4 | 0.4199 (3) | 0.9149 (2) | 0.29486 (14) | 0.0219 (4) | |
N2 | 0.1829 (3) | 0.6027 (2) | 0.56549 (14) | 0.0317 (5) | |
C5 | 0.6271 (3) | 0.8667 (2) | 0.31273 (16) | 0.0259 (5) | |
H5 | 0.6746 | 0.8616 | 0.3765 | 0.031* | |
C3 | 0.3473 (3) | 0.9234 (2) | 0.20016 (15) | 0.0279 (5) | |
H3 | 0.2083 | 0.9557 | 0.1888 | 0.033* | |
C1 | 0.6940 (3) | 0.8350 (2) | 0.13837 (16) | 0.0310 (5) | |
C6 | 0.7616 (3) | 0.8264 (2) | 0.23425 (17) | 0.0302 (5) | |
H6 | 0.9001 | 0.7928 | 0.2459 | 0.036* | |
C2 | 0.4856 (4) | 0.8829 (3) | 0.12266 (16) | 0.0329 (5) | |
H2A | 0.4380 | 0.8878 | 0.0589 | 0.039* | |
C14 | 0.4860 (4) | 0.5399 (3) | 0.65347 (18) | 0.0342 (5) | |
H14A | 0.5905 | 0.5834 | 0.6045 | 0.041* | 0.725 (7) |
H14B | 0.4585 | 0.4434 | 0.6344 | 0.041* | 0.725 (7) |
H14C | 0.5676 | 0.5506 | 0.5897 | 0.041* | 0.275 (7) |
H14D | 0.4513 | 0.4357 | 0.6689 | 0.041* | 0.275 (7) |
C9 | 0.1465 (3) | 0.6377 (3) | 0.73567 (16) | 0.0328 (5) | |
H9A | 0.1432 | 0.5353 | 0.7694 | 0.039* | |
H9B | 0.0056 | 0.6708 | 0.7161 | 0.039* | |
C10 | 0.2100 (4) | 0.7378 (3) | 0.80741 (18) | 0.0420 (6) | |
H10A | 0.2487 | 0.8319 | 0.7689 | 0.050* | |
H10B | 0.0876 | 0.7609 | 0.8511 | 0.050* | |
C7 | 0.8432 (4) | 0.7892 (3) | 0.0541 (2) | 0.0498 (7) | |
H7A | 0.7999 | 0.8425 | −0.0083 | 0.075* | |
H7B | 0.8417 | 0.6827 | 0.0527 | 0.075* | |
H7C | 0.9828 | 0.8133 | 0.0644 | 0.075* | |
C11 | 0.3866 (5) | 0.6779 (4) | 0.8716 (2) | 0.0527 (7) | |
H11C | 0.3255 | 0.6489 | 0.9387 | 0.063* | 0.275 (7) |
H11D | 0.4730 | 0.7607 | 0.8750 | 0.063* | 0.275 (7) |
H11A | 0.3484 | 0.5854 | 0.9125 | 0.063* | 0.725 (7) |
H11B | 0.4084 | 0.7504 | 0.9161 | 0.063* | 0.725 (7) |
C13A | 0.5821 (7) | 0.5103 (4) | 0.7531 (3) | 0.0337 (10) | 0.725 (7) |
H13A | 0.7239 | 0.4652 | 0.7428 | 0.040* | 0.725 (7) |
H13B | 0.5025 | 0.4363 | 0.7960 | 0.040* | 0.725 (7) |
C12A | 0.5932 (5) | 0.6462 (4) | 0.8090 (3) | 0.0385 (11) | 0.725 (7) |
H12A | 0.6210 | 0.7342 | 0.7611 | 0.046* | 0.725 (7) |
H12B | 0.7085 | 0.6273 | 0.8527 | 0.046* | 0.725 (7) |
C13B | 0.6160 (14) | 0.5780 (14) | 0.7336 (5) | 0.040 (3) | 0.275 (7) |
H13C | 0.6363 | 0.6850 | 0.7202 | 0.048* | 0.275 (7) |
H13D | 0.7535 | 0.5251 | 0.7261 | 0.048* | 0.275 (7) |
C12B | 0.5347 (15) | 0.5439 (9) | 0.8431 (7) | 0.058 (4) | 0.275 (7) |
H12C | 0.6520 | 0.5279 | 0.8857 | 0.070* | 0.275 (7) |
H12D | 0.4595 | 0.4529 | 0.8524 | 0.070* | 0.275 (7) |
H1 | 0.310 (4) | 0.843 (3) | 0.5265 (18) | 0.021 (6)* | |
H2 | 0.124 (4) | 0.521 (3) | 0.5725 (18) | 0.032 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0257 (3) | 0.0191 (3) | 0.0214 (3) | −0.00313 (19) | −0.00344 (19) | −0.00231 (19) |
O3 | 0.0365 (9) | 0.0270 (8) | 0.0266 (8) | −0.0077 (7) | −0.0107 (7) | −0.0042 (6) |
N1 | 0.0287 (10) | 0.0239 (9) | 0.0182 (9) | −0.0075 (7) | −0.0051 (8) | −0.0036 (7) |
N3 | 0.0272 (9) | 0.0264 (9) | 0.0191 (9) | −0.0062 (7) | −0.0045 (7) | −0.0029 (7) |
O1 | 0.0380 (8) | 0.0200 (7) | 0.0286 (8) | −0.0064 (6) | −0.0042 (6) | −0.0044 (6) |
O2 | 0.0283 (8) | 0.0295 (8) | 0.0315 (8) | 0.0018 (6) | −0.0067 (6) | −0.0036 (6) |
C8 | 0.0241 (10) | 0.0224 (10) | 0.0232 (10) | −0.0038 (8) | −0.0005 (8) | −0.0047 (8) |
C4 | 0.0270 (10) | 0.0196 (10) | 0.0193 (10) | −0.0070 (8) | −0.0013 (8) | −0.0004 (8) |
N2 | 0.0458 (12) | 0.0232 (10) | 0.0288 (10) | −0.0159 (9) | −0.0128 (8) | 0.0004 (8) |
C5 | 0.0285 (11) | 0.0268 (11) | 0.0233 (11) | −0.0060 (9) | −0.0033 (8) | −0.0034 (8) |
C3 | 0.0309 (11) | 0.0287 (11) | 0.0239 (11) | −0.0041 (9) | −0.0063 (9) | 0.0009 (9) |
C1 | 0.0367 (12) | 0.0303 (12) | 0.0265 (12) | −0.0116 (10) | 0.0053 (9) | −0.0040 (9) |
C6 | 0.0271 (11) | 0.0317 (12) | 0.0321 (12) | −0.0058 (9) | 0.0008 (9) | −0.0049 (9) |
C2 | 0.0447 (14) | 0.0357 (12) | 0.0197 (11) | −0.0102 (11) | −0.0040 (9) | −0.0030 (9) |
C14 | 0.0357 (12) | 0.0311 (12) | 0.0366 (13) | 0.0011 (10) | −0.0036 (10) | −0.0084 (10) |
C9 | 0.0275 (11) | 0.0419 (13) | 0.0270 (12) | −0.0031 (10) | 0.0003 (9) | 0.0019 (10) |
C10 | 0.0522 (15) | 0.0408 (14) | 0.0323 (13) | 0.0016 (12) | 0.0072 (11) | −0.0111 (11) |
C7 | 0.0543 (16) | 0.0620 (18) | 0.0334 (14) | −0.0087 (14) | 0.0125 (12) | −0.0126 (13) |
C11 | 0.0591 (17) | 0.0666 (19) | 0.0380 (15) | −0.0055 (15) | −0.0086 (13) | −0.0231 (14) |
C13A | 0.031 (2) | 0.027 (2) | 0.044 (2) | −0.0008 (17) | −0.0090 (16) | −0.0023 (16) |
C12A | 0.0355 (19) | 0.044 (2) | 0.039 (2) | −0.0081 (16) | −0.0081 (15) | −0.0097 (17) |
C13B | 0.029 (5) | 0.030 (6) | 0.060 (7) | −0.005 (5) | −0.021 (5) | 0.007 (5) |
C12B | 0.080 (8) | 0.046 (7) | 0.052 (7) | −0.009 (6) | −0.037 (6) | 0.002 (5) |
S1—N1 | 1.6321 (18) | C14—C13A | 1.506 (4) |
S1—O1 | 1.4324 (14) | C14—C13B | 1.506 (5) |
S1—O2 | 1.4260 (15) | C9—H9A | 0.9700 |
S1—C4 | 1.763 (2) | C9—H9B | 0.9700 |
O3—C8 | 1.227 (2) | C9—C10 | 1.508 (3) |
N1—C8 | 1.388 (2) | C10—H10A | 0.9700 |
N1—H1 | 0.74 (2) | C10—H10B | 0.9700 |
N3—N2 | 1.411 (2) | C10—C11 | 1.497 (4) |
N3—C14 | 1.477 (3) | C7—H7A | 0.9600 |
N3—C9 | 1.469 (3) | C7—H7B | 0.9600 |
C8—N2 | 1.341 (3) | C7—H7C | 0.9600 |
C4—C5 | 1.388 (3) | C11—H11C | 0.9700 |
C4—C3 | 1.385 (3) | C11—H11D | 0.9700 |
N2—H2 | 0.84 (2) | C11—H11A | 0.9700 |
C5—H5 | 0.9300 | C11—H11B | 0.9700 |
C5—C6 | 1.383 (3) | C11—C12A | 1.541 (4) |
C3—H3 | 0.9300 | C11—C12B | 1.543 (6) |
C3—C2 | 1.387 (3) | C13A—H13A | 0.9700 |
C1—C6 | 1.388 (3) | C13A—H13B | 0.9700 |
C1—C2 | 1.389 (3) | C13A—C12A | 1.530 (4) |
C1—C7 | 1.508 (3) | C12A—H12A | 0.9700 |
C6—H6 | 0.9300 | C12A—H12B | 0.9700 |
C2—H2A | 0.9300 | C13B—H13C | 0.9700 |
C14—H14A | 0.9700 | C13B—H13D | 0.9700 |
C14—H14B | 0.9700 | C13B—C12B | 1.530 (6) |
C14—H14C | 0.9700 | C12B—H12C | 0.9700 |
C14—H14D | 0.9700 | C12B—H12D | 0.9700 |
N1—S1—C4 | 105.32 (9) | H9A—C9—H9B | 107.8 |
O1—S1—N1 | 104.43 (9) | C10—C9—H9A | 109.1 |
O1—S1—C4 | 108.46 (9) | C10—C9—H9B | 109.1 |
O2—S1—N1 | 110.52 (9) | C9—C10—H10A | 108.0 |
O2—S1—O1 | 119.11 (9) | C9—C10—H10B | 108.0 |
O2—S1—C4 | 108.16 (9) | H10A—C10—H10B | 107.3 |
S1—N1—H1 | 116.5 (18) | C11—C10—C9 | 117.1 (2) |
C8—N1—S1 | 125.34 (15) | C11—C10—H10A | 108.0 |
C8—N1—H1 | 118.1 (18) | C11—C10—H10B | 108.0 |
N2—N3—C14 | 108.30 (16) | C1—C7—H7A | 109.5 |
N2—N3—C9 | 109.80 (16) | C1—C7—H7B | 109.5 |
C9—N3—C14 | 116.96 (17) | C1—C7—H7C | 109.5 |
O3—C8—N1 | 123.29 (19) | H7A—C7—H7B | 109.5 |
O3—C8—N2 | 123.02 (18) | H7A—C7—H7C | 109.5 |
N2—C8—N1 | 113.67 (17) | H7B—C7—H7C | 109.5 |
C5—C4—S1 | 119.46 (15) | C10—C11—H11C | 107.4 |
C3—C4—S1 | 119.37 (16) | C10—C11—H11D | 107.4 |
C3—C4—C5 | 121.1 (2) | C10—C11—H11A | 109.2 |
N3—N2—H2 | 118.8 (16) | C10—C11—H11B | 109.2 |
C8—N2—N3 | 121.41 (17) | C10—C11—C12A | 112.1 (2) |
C8—N2—H2 | 119.5 (16) | C10—C11—C12B | 119.7 (4) |
C4—C5—H5 | 120.5 | H11C—C11—H11D | 106.9 |
C6—C5—C4 | 119.0 (2) | H11A—C11—H11B | 107.9 |
C6—C5—H5 | 120.5 | C12A—C11—H11A | 109.2 |
C4—C3—H3 | 120.6 | C12A—C11—H11B | 109.2 |
C4—C3—C2 | 118.8 (2) | C12B—C11—H11C | 107.4 |
C2—C3—H3 | 120.6 | C12B—C11—H11D | 107.4 |
C6—C1—C2 | 118.6 (2) | C14—C13A—H13A | 108.1 |
C6—C1—C7 | 120.3 (2) | C14—C13A—H13B | 108.1 |
C2—C1—C7 | 121.1 (2) | C14—C13A—C12A | 116.8 (3) |
C5—C6—C1 | 121.3 (2) | H13A—C13A—H13B | 107.3 |
C5—C6—H6 | 119.4 | C12A—C13A—H13A | 108.1 |
C1—C6—H6 | 119.4 | C12A—C13A—H13B | 108.1 |
C3—C2—C1 | 121.3 (2) | C11—C12A—H12A | 109.3 |
C3—C2—H2A | 119.4 | C11—C12A—H12B | 109.3 |
C1—C2—H2A | 119.4 | C13A—C12A—C11 | 111.5 (3) |
N3—C14—H14A | 107.8 | C13A—C12A—H12A | 109.3 |
N3—C14—H14B | 107.8 | C13A—C12A—H12B | 109.3 |
N3—C14—H14C | 109.3 | H12A—C12A—H12B | 108.0 |
N3—C14—H14D | 109.3 | C14—C13B—H13C | 107.6 |
N3—C14—C13A | 118.1 (2) | C14—C13B—H13D | 107.6 |
N3—C14—C13B | 111.4 (5) | C14—C13B—C12B | 118.7 (7) |
H14A—C14—H14B | 107.1 | H13C—C13B—H13D | 107.1 |
H14C—C14—H14D | 108.0 | C12B—C13B—H13C | 107.6 |
C13A—C14—H14A | 107.8 | C12B—C13B—H13D | 107.6 |
C13A—C14—H14B | 107.8 | C11—C12B—H12C | 109.9 |
C13B—C14—H14C | 109.3 | C11—C12B—H12D | 109.9 |
C13B—C14—H14D | 109.3 | C13B—C12B—C11 | 109.1 (7) |
N3—C9—H9A | 109.1 | C13B—C12B—H12C | 109.9 |
N3—C9—H9B | 109.1 | C13B—C12B—H12D | 109.9 |
N3—C9—C10 | 112.65 (17) | H12C—C12B—H12D | 108.3 |
S1—N1—C8—O3 | 2.0 (3) | N2—N3—C14—C13A | −155.8 (2) |
S1—N1—C8—N2 | −179.65 (16) | N2—N3—C14—C13B | 176.6 (4) |
S1—C4—C5—C6 | −176.87 (15) | N2—N3—C9—C10 | −154.20 (19) |
S1—C4—C3—C2 | 176.63 (15) | C5—C4—C3—C2 | 0.0 (3) |
O3—C8—N2—N3 | −178.61 (19) | C3—C4—C5—C6 | −0.2 (3) |
N1—S1—C4—C5 | −56.79 (17) | C6—C1—C2—C3 | 0.9 (3) |
N1—S1—C4—C3 | 126.50 (16) | C2—C1—C6—C5 | −1.1 (3) |
N1—C8—N2—N3 | 3.1 (3) | C14—N3—N2—C8 | −113.7 (2) |
N3—C14—C13A—C12A | −44.3 (4) | C14—N3—C9—C10 | 81.9 (2) |
N3—C14—C13B—C12B | 69.2 (9) | C14—C13A—C12A—C11 | 85.2 (4) |
N3—C9—C10—C11 | −78.3 (3) | C14—C13B—C12B—C11 | −86.3 (11) |
O1—S1—N1—C8 | 172.44 (17) | C9—N3—N2—C8 | 117.5 (2) |
O1—S1—C4—C5 | 54.55 (17) | C9—N3—C14—C13A | −31.1 (3) |
O1—S1—C4—C3 | −122.17 (16) | C9—N3—C14—C13B | −58.8 (4) |
O2—S1—N1—C8 | 43.2 (2) | C9—C10—C11—C12A | 61.2 (3) |
O2—S1—C4—C5 | −174.97 (14) | C9—C10—C11—C12B | 17.3 (6) |
O2—S1—C4—C3 | 8.31 (19) | C10—C11—C12A—C13A | −70.4 (4) |
C4—S1—N1—C8 | −73.39 (18) | C10—C11—C12B—C13B | 51.2 (8) |
C4—C5—C6—C1 | 0.8 (3) | C7—C1—C6—C5 | −179.5 (2) |
C4—C3—C2—C1 | −0.3 (3) | C7—C1—C2—C3 | 179.2 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.74 (2) | 2.45 (2) | 3.048 (2) | 140 (2) |
N2—H2···O3ii | 0.84 (2) | 2.17 (3) | 3.011 (2) | 173 (2) |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x, −y+1, −z+1. |
C14H21N3O3S | F(000) = 332 |
Mr = 311.40 | Dx = 1.367 Mg m−3 |
Triclinic, P1 | Melting point: 444 K |
a = 6.3358 (8) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.9455 (11) Å | Cell parameters from 2355 reflections |
c = 13.5482 (15) Å | θ = 3.5–27.8° |
α = 81.976 (10)° | µ = 0.23 mm−1 |
β = 85.919 (10)° | T = 150 K |
γ = 85.273 (10)° | Plate, colourless |
V = 756.38 (15) Å3 | 0.45 × 0.3 × 0.05 mm |
Z = 2 |
Xcalibur, Ruby, Gemini ultra diffractometer | 3073 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source | 2345 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.068 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 26.4°, θmin = 3.5° |
ω scans | h = −7→7 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | k = −11→11 |
Tmin = 0.949, Tmax = 1.000 | l = −16→16 |
10897 measured reflections |
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)] = 0.050 | w = 1/[σ2(Fo2) + (0.0527P)2 + 0.3381P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.127 | (Δ/σ)max < 0.001 |
S = 1.04 | Δρmax = 0.31 e Å−3 |
3073 reflections | Δρmin = −0.47 e Å−3 |
209 parameters | Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
3 restraints | Extinction coefficient: 0.122 (7) |
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 | Occ. (<1) | |
S1 | 0.24890 (9) | 0.97737 (6) | 0.39267 (4) | 0.0186 (2) | |
O3 | 0.0600 (3) | 0.67520 (18) | 0.41208 (13) | 0.0238 (4) | |
N1 | 0.2543 (3) | 0.8355 (2) | 0.48205 (16) | 0.0193 (5) | |
N3 | 0.2923 (3) | 0.6364 (2) | 0.64536 (15) | 0.0201 (5) | |
O1 | 0.3453 (3) | 1.09391 (18) | 0.43196 (13) | 0.0235 (4) | |
O2 | 0.0407 (3) | 1.00828 (18) | 0.35765 (13) | 0.0238 (4) | |
C8 | 0.1574 (4) | 0.7010 (3) | 0.48249 (18) | 0.0187 (5) | |
C4 | 0.4182 (4) | 0.9163 (2) | 0.29485 (18) | 0.0184 (5) | |
N2 | 0.1842 (4) | 0.6016 (2) | 0.56488 (16) | 0.0254 (5) | |
C5 | 0.6273 (4) | 0.8658 (3) | 0.31301 (19) | 0.0215 (5) | |
H5 | 0.6761 | 0.8594 | 0.3767 | 0.026* | |
C3 | 0.3439 (4) | 0.9271 (3) | 0.20033 (18) | 0.0223 (6) | |
H3 | 0.2040 | 0.9615 | 0.1890 | 0.027* | |
C1 | 0.6921 (4) | 0.8355 (3) | 0.13836 (19) | 0.0250 (6) | |
C6 | 0.7612 (4) | 0.8253 (3) | 0.23417 (19) | 0.0242 (6) | |
H6 | 0.9008 | 0.7903 | 0.2458 | 0.029* | |
C2 | 0.4824 (4) | 0.8856 (3) | 0.12238 (19) | 0.0253 (6) | |
H2A | 0.4335 | 0.8916 | 0.0587 | 0.030* | |
C14 | 0.4928 (4) | 0.5390 (3) | 0.6529 (2) | 0.0257 (6) | |
H14A | 0.5982 | 0.5856 | 0.6057 | 0.031* | 0.904 (7) |
H14B | 0.4688 | 0.4426 | 0.6321 | 0.031* | 0.904 (7) |
H14C | 0.5775 | 0.5536 | 0.5903 | 0.031* | 0.096 (7) |
H14D | 0.4619 | 0.4334 | 0.6666 | 0.031* | 0.096 (7) |
C9 | 0.1465 (4) | 0.6327 (3) | 0.73527 (19) | 0.0253 (6) | |
H9A | 0.1475 | 0.5298 | 0.7693 | 0.030* | |
H9B | 0.0035 | 0.6630 | 0.7154 | 0.030* | |
C10 | 0.2061 (4) | 0.7360 (3) | 0.8070 (2) | 0.0301 (6) | |
H10A | 0.2396 | 0.8318 | 0.7685 | 0.036* | |
H10B | 0.0825 | 0.7560 | 0.8510 | 0.036* | |
C7 | 0.8416 (5) | 0.7887 (3) | 0.0541 (2) | 0.0369 (7) | |
H7A | 0.7904 | 0.8354 | −0.0087 | 0.055* | |
H7B | 0.8490 | 0.6806 | 0.0566 | 0.055* | |
H7C | 0.9804 | 0.8203 | 0.0610 | 0.055* | |
C11 | 0.3899 (5) | 0.6793 (3) | 0.8710 (2) | 0.0356 (7) | |
H11C | 0.3339 | 0.6566 | 0.9395 | 0.043* | 0.096 (7) |
H11D | 0.4822 | 0.7611 | 0.8688 | 0.043* | 0.096 (7) |
H11A | 0.3524 | 0.5888 | 0.9147 | 0.043* | 0.904 (7) |
H11B | 0.4133 | 0.7554 | 0.9127 | 0.043* | 0.904 (7) |
C13A | 0.5849 (5) | 0.5079 (4) | 0.7538 (2) | 0.0274 (8) | 0.904 (7) |
H13A | 0.7274 | 0.4609 | 0.7453 | 0.033* | 0.904 (7) |
H13B | 0.5015 | 0.4345 | 0.7955 | 0.033* | 0.904 (7) |
C12A | 0.5968 (5) | 0.6431 (3) | 0.8104 (2) | 0.0310 (9) | 0.904 (7) |
H12A | 0.6291 | 0.7311 | 0.7631 | 0.037* | 0.904 (7) |
H12B | 0.7116 | 0.6217 | 0.8552 | 0.037* | 0.904 (7) |
C13B | 0.614 (4) | 0.580 (4) | 0.7359 (12) | 0.026 (8)* | 0.096 (7) |
H13C | 0.6267 | 0.6882 | 0.7242 | 0.031* | 0.096 (7) |
H13D | 0.7560 | 0.5314 | 0.7304 | 0.031* | 0.096 (7) |
C12B | 0.525 (4) | 0.5397 (17) | 0.8434 (17) | 0.033 (9)* | 0.096 (7) |
H12C | 0.6403 | 0.5142 | 0.8879 | 0.040* | 0.096 (7) |
H12D | 0.4397 | 0.4536 | 0.8486 | 0.040* | 0.096 (7) |
H1 | 0.311 (5) | 0.841 (3) | 0.529 (2) | 0.029 (8)* | |
H2 | 0.129 (4) | 0.521 (3) | 0.571 (2) | 0.030 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0228 (3) | 0.0136 (3) | 0.0200 (3) | −0.0030 (2) | −0.0025 (2) | −0.0029 (2) |
O3 | 0.0294 (10) | 0.0205 (9) | 0.0237 (10) | −0.0070 (8) | −0.0064 (8) | −0.0047 (7) |
N1 | 0.0246 (11) | 0.0171 (11) | 0.0183 (11) | −0.0075 (9) | −0.0041 (9) | −0.0041 (8) |
N3 | 0.0213 (10) | 0.0212 (11) | 0.0191 (11) | −0.0051 (9) | −0.0015 (8) | −0.0052 (8) |
O1 | 0.0326 (10) | 0.0139 (8) | 0.0254 (10) | −0.0062 (7) | −0.0036 (8) | −0.0040 (7) |
O2 | 0.0233 (9) | 0.0211 (9) | 0.0271 (10) | 0.0010 (7) | −0.0041 (7) | −0.0038 (7) |
C8 | 0.0199 (12) | 0.0146 (12) | 0.0222 (13) | −0.0015 (10) | 0.0007 (10) | −0.0051 (10) |
C4 | 0.0225 (12) | 0.0117 (11) | 0.0206 (13) | −0.0050 (10) | −0.0011 (10) | 0.0008 (9) |
N2 | 0.0378 (13) | 0.0168 (11) | 0.0239 (12) | −0.0120 (10) | −0.0091 (10) | −0.0012 (9) |
C5 | 0.0252 (13) | 0.0181 (12) | 0.0220 (13) | −0.0063 (10) | −0.0024 (10) | −0.0024 (10) |
C3 | 0.0245 (13) | 0.0190 (12) | 0.0233 (14) | −0.0046 (10) | −0.0047 (10) | 0.0007 (10) |
C1 | 0.0302 (14) | 0.0182 (13) | 0.0267 (14) | −0.0082 (11) | 0.0046 (11) | −0.0030 (10) |
C6 | 0.0235 (13) | 0.0206 (13) | 0.0290 (14) | −0.0044 (11) | 0.0001 (11) | −0.0040 (11) |
C2 | 0.0350 (15) | 0.0248 (13) | 0.0172 (13) | −0.0086 (12) | −0.0027 (11) | −0.0021 (10) |
C14 | 0.0278 (14) | 0.0219 (13) | 0.0289 (14) | −0.0030 (11) | −0.0013 (11) | −0.0077 (11) |
C9 | 0.0231 (13) | 0.0276 (14) | 0.0246 (14) | −0.0043 (11) | −0.0003 (10) | −0.0012 (11) |
C10 | 0.0335 (15) | 0.0280 (14) | 0.0289 (15) | 0.0006 (12) | 0.0028 (12) | −0.0082 (11) |
C7 | 0.0414 (17) | 0.0422 (17) | 0.0266 (15) | −0.0029 (14) | 0.0070 (13) | −0.0082 (13) |
C11 | 0.0406 (16) | 0.0396 (17) | 0.0297 (16) | −0.0049 (14) | −0.0050 (13) | −0.0133 (13) |
C13A | 0.0235 (16) | 0.0214 (17) | 0.0369 (19) | 0.0007 (14) | −0.0061 (13) | −0.0012 (13) |
C12A | 0.0298 (17) | 0.0321 (18) | 0.0335 (19) | −0.0038 (14) | −0.0085 (13) | −0.0084 (14) |
S1—N1 | 1.627 (2) | C14—C13A | 1.506 (4) |
S1—O1 | 1.4316 (16) | C14—C13B | 1.506 (6) |
S1—O2 | 1.4259 (18) | C9—H9A | 0.9700 |
S1—C4 | 1.763 (3) | C9—H9B | 0.9700 |
O3—C8 | 1.230 (3) | C9—C10 | 1.518 (4) |
N1—C8 | 1.395 (3) | C10—H10A | 0.9700 |
N1—H1 | 0.76 (3) | C10—H10B | 0.9700 |
N3—N2 | 1.411 (3) | C10—C11 | 1.513 (4) |
N3—C14 | 1.481 (3) | C7—H7A | 0.9600 |
N3—C9 | 1.474 (3) | C7—H7B | 0.9600 |
C8—N2 | 1.338 (3) | C7—H7C | 0.9600 |
C4—C5 | 1.391 (3) | C11—H11C | 0.9700 |
C4—C3 | 1.384 (3) | C11—H11D | 0.9700 |
N2—H2 | 0.82 (3) | C11—H11A | 0.9700 |
C5—H5 | 0.9300 | C11—H11B | 0.9700 |
C5—C6 | 1.386 (3) | C11—C12A | 1.532 (4) |
C3—H3 | 0.9300 | C11—C12B | 1.532 (6) |
C3—C2 | 1.395 (4) | C13A—H13A | 0.9700 |
C1—C6 | 1.388 (4) | C13A—H13B | 0.9700 |
C1—C2 | 1.389 (4) | C13A—C12A | 1.529 (4) |
C1—C7 | 1.513 (4) | C12A—H12A | 0.9700 |
C6—H6 | 0.9300 | C12A—H12B | 0.9700 |
C2—H2A | 0.9300 | C13B—H13C | 0.9700 |
C14—H14A | 0.9700 | C13B—H13D | 0.9700 |
C14—H14B | 0.9700 | C13B—C12B | 1.528 (6) |
C14—H14C | 0.9700 | C12B—H12C | 0.9700 |
C14—H14D | 0.9700 | C12B—H12D | 0.9700 |
N1—S1—C4 | 105.29 (11) | H9A—C9—H9B | 107.8 |
O1—S1—N1 | 104.48 (10) | C10—C9—H9A | 109.1 |
O1—S1—C4 | 108.61 (10) | C10—C9—H9B | 109.1 |
O2—S1—N1 | 110.59 (10) | C9—C10—H10A | 108.1 |
O2—S1—O1 | 118.97 (10) | C9—C10—H10B | 108.1 |
O2—S1—C4 | 108.07 (11) | H10A—C10—H10B | 107.3 |
S1—N1—H1 | 120 (2) | C11—C10—C9 | 116.7 (2) |
C8—N1—S1 | 125.48 (18) | C11—C10—H10A | 108.1 |
C8—N1—H1 | 115 (2) | C11—C10—H10B | 108.1 |
N2—N3—C14 | 108.65 (18) | C1—C7—H7A | 109.5 |
N2—N3—C9 | 109.51 (18) | C1—C7—H7B | 109.5 |
C9—N3—C14 | 117.3 (2) | C1—C7—H7C | 109.5 |
O3—C8—N1 | 122.6 (2) | H7A—C7—H7B | 109.5 |
O3—C8—N2 | 123.2 (2) | H7A—C7—H7C | 109.5 |
N2—C8—N1 | 114.2 (2) | H7B—C7—H7C | 109.5 |
C5—C4—S1 | 119.30 (18) | C10—C11—H11C | 108.1 |
C3—C4—S1 | 119.32 (19) | C10—C11—H11D | 108.1 |
C3—C4—C5 | 121.3 (2) | C10—C11—H11A | 108.9 |
N3—N2—H2 | 119 (2) | C10—C11—H11B | 108.9 |
C8—N2—N3 | 121.7 (2) | C10—C11—C12A | 113.5 (2) |
C8—N2—H2 | 119 (2) | C10—C11—C12B | 117.0 (11) |
C4—C5—H5 | 120.7 | H11C—C11—H11D | 107.3 |
C6—C5—C4 | 118.6 (2) | H11A—C11—H11B | 107.7 |
C6—C5—H5 | 120.7 | C12A—C11—H11A | 108.9 |
C4—C3—H3 | 120.6 | C12A—C11—H11B | 108.9 |
C4—C3—C2 | 118.9 (2) | C12B—C11—H11C | 108.1 |
C2—C3—H3 | 120.6 | C12B—C11—H11D | 108.1 |
C6—C1—C2 | 118.6 (2) | C14—C13A—H13A | 108.0 |
C6—C1—C7 | 120.3 (2) | C14—C13A—H13B | 108.0 |
C2—C1—C7 | 121.1 (2) | C14—C13A—C12A | 117.2 (3) |
C5—C6—C1 | 121.6 (2) | H13A—C13A—H13B | 107.2 |
C5—C6—H6 | 119.2 | C12A—C13A—H13A | 108.0 |
C1—C6—H6 | 119.2 | C12A—C13A—H13B | 108.0 |
C3—C2—H2A | 119.5 | C11—C12A—H12A | 109.1 |
C1—C2—C3 | 121.0 (2) | C11—C12A—H12B | 109.1 |
C1—C2—H2A | 119.5 | C13A—C12A—C11 | 112.6 (2) |
N3—C14—H14A | 108.1 | C13A—C12A—H12A | 109.1 |
N3—C14—H14B | 108.1 | C13A—C12A—H12B | 109.1 |
N3—C14—H14C | 109.9 | H12A—C12A—H12B | 107.8 |
N3—C14—H14D | 109.9 | C14—C13B—H13C | 107.7 |
N3—C14—C13A | 116.9 (2) | C14—C13B—H13D | 107.7 |
N3—C14—C13B | 109.1 (13) | C14—C13B—C12B | 118.3 (17) |
H14A—C14—H14B | 107.3 | H13C—C13B—H13D | 107.1 |
H14C—C14—H14D | 108.3 | C12B—C13B—H13C | 107.7 |
C13A—C14—H14A | 108.1 | C12B—C13B—H13D | 107.7 |
C13A—C14—H14B | 108.1 | C11—C12B—H12C | 110.4 |
C13B—C14—H14C | 109.9 | C11—C12B—H12D | 110.4 |
C13B—C14—H14D | 109.9 | C13B—C12B—C11 | 106.8 (16) |
N3—C9—H9A | 109.1 | C13B—C12B—H12C | 110.4 |
N3—C9—H9B | 109.1 | C13B—C12B—H12D | 110.4 |
N3—C9—C10 | 112.45 (19) | H12C—C12B—H12D | 108.6 |
S1—N1—C8—O3 | 1.7 (3) | N2—N3—C14—C13A | −154.8 (2) |
S1—N1—C8—N2 | −179.79 (18) | N2—N3—C14—C13B | 177.7 (11) |
S1—C4—C5—C6 | −176.84 (17) | N2—N3—C9—C10 | −152.5 (2) |
S1—C4—C3—C2 | 176.79 (17) | C5—C4—C3—C2 | 0.3 (3) |
O3—C8—N2—N3 | −178.4 (2) | C3—C4—C5—C6 | −0.4 (3) |
N1—S1—C4—C5 | −56.1 (2) | C6—C1—C2—C3 | 0.9 (3) |
N1—S1—C4—C3 | 127.41 (18) | C2—C1—C6—C5 | −1.0 (3) |
N1—C8—N2—N3 | 3.2 (3) | C14—N3—N2—C8 | −112.8 (3) |
N3—C14—C13A—C12A | −46.6 (4) | C14—N3—C9—C10 | 83.1 (3) |
N3—C14—C13B—C12B | 70 (2) | C14—C13A—C12A—C11 | 85.3 (4) |
N3—C9—C10—C11 | −77.5 (3) | C14—C13B—C12B—C11 | −94 (3) |
O1—S1—N1—C8 | 172.8 (2) | C9—N3—N2—C8 | 117.8 (3) |
O1—S1—C4—C5 | 55.4 (2) | C9—N3—C14—C13A | −30.0 (3) |
O1—S1—C4—C3 | −121.15 (18) | C9—N3—C14—C13B | −57.5 (11) |
O2—S1—N1—C8 | 43.7 (2) | C9—C10—C11—C12A | 57.9 (3) |
O2—S1—C4—C5 | −174.27 (17) | C9—C10—C11—C12B | 11.8 (11) |
O2—S1—C4—C3 | 9.2 (2) | C10—C11—C12A—C13A | −66.9 (3) |
C4—S1—N1—C8 | −72.8 (2) | C10—C11—C12B—C13B | 58.7 (18) |
C4—C5—C6—C1 | 0.7 (3) | C7—C1—C6—C5 | −179.3 (2) |
C4—C3—C2—C1 | −0.6 (3) | C7—C1—C2—C3 | 179.2 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.76 (3) | 2.41 (3) | 3.013 (3) | 137 (3) |
N2—H2···O3ii | 0.82 (3) | 2.18 (3) | 2.995 (3) | 172 (3) |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x, −y+1, −z+1. |
C14H21N3O3S | F(000) = 332 |
Mr = 311.40 | Dx = 1.373 Mg m−3 |
Triclinic, P1 | Melting point: 444 K |
a = 6.3091 (10) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 8.9270 (15) Å | Cell parameters from 1573 reflections |
c = 13.576 (3) Å | θ = 3.5–28.6° |
α = 81.882 (16)° | µ = 0.23 mm−1 |
β = 86.073 (16)° | T = 100 K |
γ = 85.167 (13)° | Plate, colourless |
V = 753.0 (2) Å3 | 0.45 × 0.3 × 0.05 mm |
Z = 2 |
Xcalibur, Ruby, Gemini ultra diffractometer | 3057 independent reflections |
Radiation source: fine-focus sealed X-ray tube, Enhance (Mo) X-ray Source | 2081 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.094 |
Detector resolution: 10.3457 pixels mm-1 | θmax = 26.4°, θmin = 3.5° |
ω scans | h = −7→7 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | k = −11→11 |
Tmin = 0.753, Tmax = 1.000 | l = −16→16 |
10088 measured reflections |
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)] = 0.069 | w = 1/[σ2(Fo2) + (0.0721P)2 + 0.2853P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.173 | (Δ/σ)max < 0.001 |
S = 1.03 | Δρmax = 0.47 e Å−3 |
3057 reflections | Δρmin = −0.63 e Å−3 |
200 parameters | Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.054 (6) |
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 | 0.24796 (13) | 0.97848 (9) | 0.39256 (6) | 0.0193 (3) | |
O3 | 0.0587 (3) | 0.6762 (2) | 0.41186 (17) | 0.0220 (6) | |
N1 | 0.2545 (4) | 0.8362 (3) | 0.4822 (2) | 0.0178 (7) | |
N3 | 0.2938 (4) | 0.6344 (3) | 0.6454 (2) | 0.0201 (7) | |
O1 | 0.3462 (3) | 1.0952 (2) | 0.43185 (17) | 0.0210 (6) | |
O2 | 0.0397 (3) | 1.0102 (2) | 0.35772 (18) | 0.0226 (6) | |
C8 | 0.1579 (5) | 0.7009 (4) | 0.4825 (3) | 0.0200 (8) | |
C4 | 0.4168 (5) | 0.9174 (3) | 0.2949 (2) | 0.0176 (7) | |
N2 | 0.1844 (5) | 0.6006 (3) | 0.5649 (2) | 0.0222 (7) | |
C5 | 0.6262 (5) | 0.8655 (3) | 0.3129 (3) | 0.0202 (8) | |
H5 | 0.6753 | 0.8580 | 0.3766 | 0.024* | |
C3 | 0.3423 (5) | 0.9291 (4) | 0.2002 (3) | 0.0206 (8) | |
H3 | 0.2019 | 0.9641 | 0.1888 | 0.025* | |
C1 | 0.6918 (5) | 0.8360 (4) | 0.1380 (3) | 0.0230 (8) | |
C6 | 0.7617 (5) | 0.8247 (4) | 0.2337 (3) | 0.0239 (8) | |
H6 | 0.9018 | 0.7892 | 0.2453 | 0.029* | |
C2 | 0.4798 (5) | 0.8878 (4) | 0.1225 (3) | 0.0234 (8) | |
H2A | 0.4299 | 0.8948 | 0.0590 | 0.028* | |
C14 | 0.4970 (5) | 0.5378 (4) | 0.6527 (3) | 0.0240 (8) | |
H14A | 0.6026 | 0.5861 | 0.6063 | 0.029* | |
H14B | 0.4751 | 0.4415 | 0.6310 | 0.029* | |
C9 | 0.1481 (5) | 0.6295 (4) | 0.7354 (3) | 0.0217 (8) | |
H9A | 0.1506 | 0.5261 | 0.7692 | 0.026* | |
H9B | 0.0040 | 0.6593 | 0.7157 | 0.026* | |
C10 | 0.2070 (5) | 0.7335 (4) | 0.8079 (3) | 0.0259 (8) | |
H10A | 0.2370 | 0.8305 | 0.7698 | 0.031* | |
H10B | 0.0832 | 0.7514 | 0.8523 | 0.031* | |
C7 | 0.8410 (6) | 0.7885 (4) | 0.0541 (3) | 0.0321 (9) | |
H7A | 0.8045 | 0.8490 | −0.0074 | 0.048* | |
H7B | 0.8283 | 0.6834 | 0.0492 | 0.048* | |
H7C | 0.9850 | 0.8028 | 0.0673 | 0.048* | |
C11 | 0.3933 (6) | 0.6791 (4) | 0.8708 (3) | 0.0285 (9) | |
H11A | 0.3572 | 0.5891 | 0.9156 | 0.034* | |
H11B | 0.4170 | 0.7567 | 0.9112 | 0.034* | |
C13 | 0.5881 (5) | 0.5058 (4) | 0.7545 (3) | 0.0242 (8) | |
H13A | 0.7308 | 0.4576 | 0.7468 | 0.029* | |
H13B | 0.5029 | 0.4330 | 0.7958 | 0.029* | |
C12 | 0.6003 (5) | 0.6417 (4) | 0.8107 (3) | 0.0268 (9) | |
H12A | 0.7156 | 0.6201 | 0.8556 | 0.032* | |
H12B | 0.6330 | 0.7297 | 0.7633 | 0.032* | |
H1 | 0.317 (6) | 0.839 (4) | 0.530 (3) | 0.028 (11)* | |
H2 | 0.131 (6) | 0.516 (5) | 0.566 (3) | 0.032 (11)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0216 (5) | 0.0104 (4) | 0.0270 (5) | −0.0015 (3) | −0.0028 (4) | −0.0049 (3) |
O3 | 0.0248 (13) | 0.0146 (12) | 0.0283 (14) | −0.0036 (10) | −0.0058 (11) | −0.0053 (10) |
N1 | 0.0217 (15) | 0.0096 (14) | 0.0238 (17) | −0.0032 (12) | −0.0057 (13) | −0.0040 (12) |
N3 | 0.0193 (14) | 0.0154 (15) | 0.0274 (17) | −0.0014 (12) | −0.0034 (12) | −0.0088 (12) |
O1 | 0.0256 (12) | 0.0078 (11) | 0.0306 (14) | −0.0026 (10) | −0.0039 (10) | −0.0040 (9) |
O2 | 0.0216 (12) | 0.0138 (12) | 0.0326 (15) | 0.0011 (10) | −0.0032 (10) | −0.0047 (10) |
C8 | 0.0175 (17) | 0.0131 (17) | 0.030 (2) | 0.0020 (14) | −0.0033 (15) | −0.0053 (15) |
C4 | 0.0204 (17) | 0.0061 (15) | 0.0260 (19) | −0.0026 (14) | −0.0013 (14) | −0.0001 (13) |
N2 | 0.0299 (17) | 0.0120 (15) | 0.0269 (17) | −0.0069 (13) | −0.0076 (13) | −0.0046 (12) |
C5 | 0.0242 (18) | 0.0101 (16) | 0.027 (2) | −0.0054 (14) | −0.0041 (15) | −0.0017 (13) |
C3 | 0.0231 (18) | 0.0098 (16) | 0.028 (2) | −0.0016 (14) | −0.0027 (15) | 0.0000 (14) |
C1 | 0.0239 (18) | 0.0109 (16) | 0.035 (2) | −0.0045 (15) | 0.0008 (16) | −0.0055 (14) |
C6 | 0.0206 (18) | 0.0144 (18) | 0.038 (2) | −0.0031 (15) | −0.0025 (16) | −0.0058 (15) |
C2 | 0.033 (2) | 0.0171 (18) | 0.0216 (19) | −0.0049 (16) | −0.0030 (16) | −0.0042 (14) |
C14 | 0.0249 (18) | 0.0168 (18) | 0.033 (2) | −0.0028 (15) | 0.0000 (16) | −0.0120 (15) |
C9 | 0.0205 (17) | 0.0148 (17) | 0.030 (2) | −0.0014 (14) | −0.0022 (15) | −0.0034 (14) |
C10 | 0.0272 (19) | 0.0203 (19) | 0.032 (2) | −0.0018 (16) | 0.0018 (16) | −0.0107 (15) |
C7 | 0.036 (2) | 0.031 (2) | 0.031 (2) | −0.0045 (18) | 0.0048 (17) | −0.0098 (17) |
C11 | 0.030 (2) | 0.024 (2) | 0.034 (2) | −0.0023 (16) | −0.0042 (17) | −0.0125 (16) |
C13 | 0.0208 (18) | 0.0156 (18) | 0.036 (2) | −0.0002 (15) | −0.0039 (16) | −0.0037 (15) |
C12 | 0.0217 (18) | 0.0245 (19) | 0.037 (2) | 0.0007 (16) | −0.0073 (16) | −0.0115 (16) |
S1—N1 | 1.630 (3) | C2—H2A | 0.9300 |
S1—O1 | 1.437 (2) | C14—H14A | 0.9700 |
S1—O2 | 1.420 (2) | C14—H14B | 0.9700 |
S1—C4 | 1.761 (3) | C14—C13 | 1.514 (5) |
O3—C8 | 1.235 (4) | C9—H9A | 0.9700 |
N1—C8 | 1.398 (4) | C9—H9B | 0.9700 |
N1—H1 | 0.78 (4) | C9—C10 | 1.528 (5) |
N3—N2 | 1.411 (4) | C10—H10A | 0.9700 |
N3—C14 | 1.485 (4) | C10—H10B | 0.9700 |
N3—C9 | 1.477 (4) | C10—C11 | 1.507 (5) |
C8—N2 | 1.341 (4) | C7—H7A | 0.9600 |
C4—C5 | 1.388 (5) | C7—H7B | 0.9600 |
C4—C3 | 1.387 (5) | C7—H7C | 0.9600 |
N2—H2 | 0.85 (4) | C11—H11A | 0.9700 |
C5—H5 | 0.9300 | C11—H11B | 0.9700 |
C5—C6 | 1.398 (5) | C11—C12 | 1.530 (5) |
C3—H3 | 0.9300 | C13—H13A | 0.9700 |
C3—C2 | 1.390 (5) | C13—H13B | 0.9700 |
C1—C6 | 1.388 (5) | C13—C12 | 1.532 (5) |
C1—C2 | 1.398 (5) | C12—H12A | 0.9700 |
C1—C7 | 1.512 (5) | C12—H12B | 0.9700 |
C6—H6 | 0.9300 | ||
N1—S1—C4 | 105.42 (15) | H14A—C14—H14B | 107.3 |
O1—S1—N1 | 104.20 (14) | C13—C14—H14A | 108.2 |
O1—S1—C4 | 108.49 (14) | C13—C14—H14B | 108.2 |
O2—S1—N1 | 110.89 (14) | N3—C9—H9A | 109.0 |
O2—S1—O1 | 118.99 (14) | N3—C9—H9B | 109.0 |
O2—S1—C4 | 108.02 (15) | N3—C9—C10 | 112.7 (2) |
S1—N1—H1 | 121 (3) | H9A—C9—H9B | 107.8 |
C8—N1—S1 | 125.3 (2) | C10—C9—H9A | 109.0 |
C8—N1—H1 | 114 (3) | C10—C9—H9B | 109.0 |
N2—N3—C14 | 109.1 (3) | C9—C10—H10A | 108.0 |
N2—N3—C9 | 109.5 (2) | C9—C10—H10B | 108.0 |
C9—N3—C14 | 117.3 (3) | H10A—C10—H10B | 107.3 |
O3—C8—N1 | 122.3 (3) | C11—C10—C9 | 117.1 (3) |
O3—C8—N2 | 123.3 (3) | C11—C10—H10A | 108.0 |
N2—C8—N1 | 114.5 (3) | C11—C10—H10B | 108.0 |
C5—C4—S1 | 119.4 (3) | C1—C7—H7A | 109.5 |
C3—C4—S1 | 119.6 (3) | C1—C7—H7B | 109.5 |
C3—C4—C5 | 121.0 (3) | C1—C7—H7C | 109.5 |
N3—N2—H2 | 122 (3) | H7A—C7—H7B | 109.5 |
C8—N2—N3 | 121.7 (3) | H7A—C7—H7C | 109.5 |
C8—N2—H2 | 116 (3) | H7B—C7—H7C | 109.5 |
C4—C5—H5 | 120.6 | C10—C11—H11A | 108.7 |
C4—C5—C6 | 118.8 (3) | C10—C11—H11B | 108.7 |
C6—C5—H5 | 120.6 | C10—C11—C12 | 114.1 (3) |
C4—C3—H3 | 120.4 | H11A—C11—H11B | 107.6 |
C4—C3—C2 | 119.2 (3) | C12—C11—H11A | 108.7 |
C2—C3—H3 | 120.4 | C12—C11—H11B | 108.7 |
C6—C1—C2 | 118.3 (3) | C14—C13—H13A | 108.0 |
C6—C1—C7 | 120.3 (3) | C14—C13—H13B | 108.0 |
C2—C1—C7 | 121.4 (3) | C14—C13—C12 | 117.0 (3) |
C5—C6—H6 | 119.3 | H13A—C13—H13B | 107.3 |
C1—C6—C5 | 121.5 (3) | C12—C13—H13A | 108.0 |
C1—C6—H6 | 119.3 | C12—C13—H13B | 108.0 |
C3—C2—C1 | 121.2 (3) | C11—C12—C13 | 112.8 (3) |
C3—C2—H2A | 119.4 | C11—C12—H12A | 109.0 |
C1—C2—H2A | 119.4 | C11—C12—H12B | 109.0 |
N3—C14—H14A | 108.2 | C13—C12—H12A | 109.0 |
N3—C14—H14B | 108.2 | C13—C12—H12B | 109.0 |
N3—C14—C13 | 116.4 (3) | H12A—C12—H12B | 107.8 |
S1—N1—C8—O3 | 1.1 (5) | C4—C5—C6—C1 | 0.4 (5) |
S1—N1—C8—N2 | −179.7 (3) | C4—C3—C2—C1 | −0.5 (5) |
S1—C4—C5—C6 | −176.8 (2) | N2—N3—C14—C13 | −154.4 (3) |
S1—C4—C3—C2 | 176.8 (2) | N2—N3—C9—C10 | −152.0 (3) |
O3—C8—N2—N3 | −178.2 (3) | C5—C4—C3—C2 | 0.1 (4) |
N1—S1—C4—C5 | −55.4 (3) | C3—C4—C5—C6 | −0.1 (4) |
N1—S1—C4—C3 | 127.9 (2) | C6—C1—C2—C3 | 0.9 (5) |
N1—C8—N2—N3 | 2.5 (5) | C2—C1—C6—C5 | −0.8 (5) |
N3—C14—C13—C12 | −48.0 (4) | C14—N3—N2—C8 | −111.9 (4) |
N3—C9—C10—C11 | −76.8 (4) | C14—N3—C9—C10 | 82.9 (3) |
O1—S1—N1—C8 | 173.3 (3) | C14—C13—C12—C11 | 85.8 (4) |
O1—S1—C4—C5 | 55.8 (3) | C9—N3—N2—C8 | 118.5 (3) |
O1—S1—C4—C3 | −121.0 (2) | C9—N3—C14—C13 | −29.1 (4) |
O2—S1—N1—C8 | 44.2 (3) | C9—C10—C11—C12 | 56.2 (4) |
O2—S1—C4—C5 | −174.0 (2) | C10—C11—C12—C13 | −65.9 (4) |
O2—S1—C4—C3 | 9.3 (3) | C7—C1—C6—C5 | −178.9 (3) |
C4—S1—N1—C8 | −72.5 (3) | C7—C1—C2—C3 | 178.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.78 (4) | 2.37 (4) | 2.991 (3) | 137 (4) |
N2—H2···O3ii | 0.85 (4) | 2.15 (4) | 2.985 (3) | 168 (4) |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x, −y+1, −z+1. |
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