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Ten new crystal structures of
cis and
trans bicyclic diketopiperazines (DKPs) of thia-pipecolic acid (with sulfur in the β, γ or δ position) or thia-proline (with sulfur in the β or γ position) and
N-methyl phenylalanine [(NMe)Phe]:
cyclo[(β-S)Pip-(NMe)Phe],
cyclo[(γ-S)Pip-(NMe)Phe],
cyclo[(δ-S)Pip-(NMe)Phe],
cyclo[(β-S)Pro-(NMe)Phe] and
cyclo[(γ-S)Pro-(NMe)Phe] were determined with X-ray crystallography. Density functional theory calculations of these molecules in the gas phase succeed in reproducing the observed molecular conformations in the crystal remarkably well. This illustrates the weak to moderate impact of intermolecular packing forces in the absence of classical N—H
O hydrogen bonds. The effect of sulfur on the geometry of the DKP ring and details of amide bond non-planarity are discussed. Molecular flexibility of the DKP ring, as estimated from the calculated deformation energies of its endocyclic ring torsion angles, is not in general the decisive factor for the occurrence of multiple symmetry independent molecules in the unit cell (
Z′ > 1), though in some cases a correlation is observed.
Supporting information
| Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520617014731/dk5056sup1.cif Contains datablocks 4a, 4b, 6a, 6b, 8a, 8b, 12a, 12b, 14a, 14b |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520617014731/dk50564asup2.hkl Contains datablock 4a |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520617014731/dk50564bsup3.hkl Contains datablock 4b |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520617014731/dk50566asup4.hkl Contains datablock 6a |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520617014731/dk50566bsup5.hkl Contains datablock 6b |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520617014731/dk50568asup6.hkl Contains datablock 8a |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520617014731/dk50568bsup7.hkl Contains datablock 8b |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520617014731/dk505612asup8.hkl Contains datablock 12a |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520617014731/dk505612bsup9.hkl Contains datablock 12b |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520617014731/dk505614asup10.hkl Contains datablock 14a |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520617014731/dk505614bsup11.hkl Contains datablock 14b |
| Portable Document Format (PDF) file https://doi.org/10.1107/S2052520617014731/dk5056sup12.pdf Fig. S1, Tables S1-S2 |
CCDC references: 1400449; 1400450; 1400451; 1400452; 1400453; 1400454; 1400455; 1400456; 1400457; 1400458
Data collection: COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997) for (4a), (4b), (6a), (6b), (8a), (8b); Bruker APEX2 for (12a), (12b), (14a), (14b). Cell refinement: COLLECT and DENZO for (4a), (4b), (6a), (6b), (8a), (8b); Bruker SAINT for (12a), (12b), (14a), (14b). Data reduction: COLLECT and DENZO for (4a), (4b), (6a), (6b), (8a), (8b); Bruker SAINT for (12a), (12b), (14a), (14b). Program(s) used to solve structure: SIR92 (Altomare et al., 1994) for (4a), (4b), (6a), (6b), (8a), (8b); SHELXS97 (Sheldrick, 2008) for (12a), (12b), (14a), (14b). For all structures, program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2014).
Crystal data top
2(C15H18N2O2S)·H2O | Dx = 1.332 Mg m−3 |
Mr = 598.76 | Mo Kα radiation, λ = 0.71070 Å |
Trigonal, P31 | Cell parameters from 54195 reflections |
Hall symbol: P 31 | θ = 1–27.8° |
a = 8.4102 (2) Å | µ = 0.22 mm−1 |
c = 36.562 (1) Å | T = 150 K |
V = 2239.61 (10) Å3 | Plate, colourless |
Z = 3 | 0.5 × 0.5 × 0.2 mm |
F(000) = 954 | |
Data collection top
Nonius KappaCCD area detector diffractometer | 5051 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.051 |
Graphite monochromator | θmax = 26.0°, θmin = 4.0° |
Detector resolution: 9.091 pixels mm-1 | h = −10→10 |
φ and ω scans to fill the Ewald sphere | k = −8→8 |
15456 measured reflections | l = −44→44 |
5110 independent reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.113 | w = 1/[σ2(Fo2) + (0.0502P)2 + 1.5374P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
5110 reflections | Δρmax = 0.37 e Å−3 |
373 parameters | Δρmin = −0.28 e Å−3 |
1 restraint | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.01 (12) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F2, conventional R-factors R are based
on F, with F set to zero for negative F2. The threshold expression of
F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F2 are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N11 | 0.3901 (5) | 0.5157 (6) | 0.13434 (10) | 0.0365 (9) | |
C12 | 0.5655 (7) | 0.6501 (6) | 0.13601 (12) | 0.0341 (10) | |
O12 | 0.6366 (5) | 0.7696 (5) | 0.11261 (10) | 0.0466 (9) | |
C13 | 0.6815 (7) | 0.6559 (7) | 0.16871 (13) | 0.0402 (10) | |
H13 | 0.7253 | 0.7750 | 0.1806 | 0.048* | |
N14 | 0.5804 (6) | 0.5150 (6) | 0.19644 (10) | 0.0386 (9) | |
C14 | 0.6782 (9) | 0.5387 (9) | 0.23141 (13) | 0.0539 (14) | |
H14A | 0.5909 | 0.4897 | 0.2510 | 0.081* | |
H14B | 0.7613 | 0.6669 | 0.2356 | 0.081* | |
H14C | 0.7460 | 0.4748 | 0.2303 | 0.081* | |
C15 | 0.4104 (7) | 0.3733 (7) | 0.19289 (12) | 0.0393 (11) | |
O15 | 0.3273 (6) | 0.2514 (6) | 0.21654 (10) | 0.0548 (10) | |
C16 | 0.3100 (7) | 0.3562 (7) | 0.15723 (12) | 0.0392 (11) | |
H16 | 0.1858 | 0.3298 | 0.1635 | 0.047* | |
S17 | 0.28769 (18) | 0.1535 (2) | 0.13302 (4) | 0.0487 (3) | |
C18 | 0.1582 (7) | 0.1636 (8) | 0.09461 (17) | 0.0515 (13) | |
H18A | 0.1434 | 0.0724 | 0.0766 | 0.062* | |
H18B | 0.0370 | 0.1349 | 0.1028 | 0.062* | |
C19 | 0.2546 (8) | 0.3543 (9) | 0.07682 (13) | 0.0519 (14) | |
H19A | 0.3749 | 0.3817 | 0.0683 | 0.062* | |
H19B | 0.1843 | 0.3533 | 0.0557 | 0.062* | |
C110 | 0.2756 (8) | 0.5003 (8) | 0.10224 (14) | 0.0475 (12) | |
H11A | 0.1554 | 0.4739 | 0.1106 | 0.057* | |
H11B | 0.3317 | 0.6167 | 0.0894 | 0.057* | |
C111 | 0.8543 (7) | 0.6530 (7) | 0.15442 (13) | 0.0389 (10) | |
H11C | 0.9284 | 0.7638 | 0.1403 | 0.047* | |
H11D | 0.9269 | 0.6553 | 0.1752 | 0.047* | |
C112 | 0.8127 (5) | 0.4905 (6) | 0.13119 (12) | 0.0293 (9) | |
C113 | 0.7797 (6) | 0.3272 (7) | 0.14774 (14) | 0.0346 (10) | |
H113 | 0.7882 | 0.3214 | 0.1730 | 0.041* | |
C114 | 0.7342 (6) | 0.1734 (6) | 0.12650 (14) | 0.0376 (10) | |
H114 | 0.7138 | 0.0651 | 0.1375 | 0.045* | |
C115 | 0.7190 (7) | 0.1818 (8) | 0.08865 (15) | 0.0465 (12) | |
H115 | 0.6851 | 0.0777 | 0.0745 | 0.056* | |
C116 | 0.7538 (7) | 0.3434 (7) | 0.07204 (13) | 0.0420 (12) | |
H116 | 0.7466 | 0.3491 | 0.0467 | 0.050* | |
C117 | 0.8005 (6) | 0.4996 (6) | 0.09355 (13) | 0.0374 (10) | |
H117 | 0.8230 | 0.6086 | 0.0825 | 0.045* | |
N21 | 0.3464 (5) | 0.5511 (5) | 0.29836 (10) | 0.0334 (8) | |
C22 | 0.4839 (6) | 0.7289 (6) | 0.29613 (11) | 0.0318 (9) | |
O22 | 0.6062 (4) | 0.7998 (5) | 0.31883 (10) | 0.0426 (8) | |
C23 | 0.4884 (6) | 0.8361 (6) | 0.26299 (12) | 0.0331 (9) | |
H23 | 0.6059 | 0.8741 | 0.2508 | 0.040* | |
N24 | 0.3462 (5) | 0.7350 (5) | 0.23596 (9) | 0.0335 (8) | |
C24 | 0.3699 (9) | 0.8292 (8) | 0.20022 (13) | 0.0484 (12) | |
H24A | 0.3113 | 0.7392 | 0.1813 | 0.073* | |
H24B | 0.4984 | 0.9036 | 0.1949 | 0.073* | |
H24C | 0.3152 | 0.9056 | 0.2015 | 0.073* | |
C25 | 0.2004 (6) | 0.5682 (6) | 0.24092 (12) | 0.0349 (10) | |
O25 | 0.0815 (5) | 0.4888 (5) | 0.21737 (9) | 0.0453 (8) | |
C26 | 0.1824 (6) | 0.4705 (6) | 0.27707 (12) | 0.0323 (9) | |
H26 | 0.1521 | 0.3446 | 0.2713 | 0.039* | |
S27 | −0.01290 (17) | 0.45711 (18) | 0.30100 (4) | 0.0396 (3) | |
C28 | 0.0017 (7) | 0.3327 (7) | 0.34046 (14) | 0.0422 (11) | |
H28A | −0.0891 | 0.3194 | 0.3584 | 0.051* | |
H28B | −0.0275 | 0.2105 | 0.3328 | 0.051* | |
C29 | 0.1901 (7) | 0.4276 (7) | 0.35825 (14) | 0.0461 (12) | |
H29A | 0.1892 | 0.3588 | 0.3796 | 0.055* | |
H29B | 0.2204 | 0.5497 | 0.3661 | 0.055* | |
C210 | 0.3357 (7) | 0.4411 (7) | 0.33090 (13) | 0.0431 (11) | |
H21A | 0.4545 | 0.4973 | 0.3428 | 0.052* | |
H21B | 0.3052 | 0.3187 | 0.3232 | 0.052* | |
C211 | 0.4930 (6) | 1.0149 (7) | 0.27509 (12) | 0.0360 (9) | |
H21C | 0.6037 | 1.0890 | 0.2892 | 0.043* | |
H21D | 0.4982 | 1.0845 | 0.2535 | 0.043* | |
C212 | 0.3296 (6) | 0.9802 (6) | 0.29763 (11) | 0.0277 (9) | |
C213 | 0.3308 (6) | 0.9645 (6) | 0.33568 (12) | 0.0315 (9) | |
H213 | 0.4362 | 0.9817 | 0.3475 | 0.038* | |
C214 | 0.1767 (7) | 0.9236 (6) | 0.35570 (12) | 0.0354 (10) | |
H214 | 0.1792 | 0.9148 | 0.3810 | 0.042* | |
C215 | 0.0169 (6) | 0.8953 (6) | 0.33857 (12) | 0.0329 (9) | |
H215 | −0.0883 | 0.8628 | 0.3522 | 0.040* | |
C216 | 0.0161 (6) | 0.9160 (6) | 0.30082 (12) | 0.0354 (10) | |
H216 | −0.0875 | 0.9045 | 0.2892 | 0.042* | |
C217 | 0.1693 (6) | 0.9534 (6) | 0.28075 (12) | 0.0307 (9) | |
H217 | 0.1660 | 0.9610 | 0.2554 | 0.037* | |
O1W | −0.0873 (5) | 1.0814 (5) | 0.21503 (12) | 0.0500 (9) | |
H1W | −0.0615 | 1.1988 | 0.2196 | 0.060* | |
H2W | 0.0174 | 1.1017 | 0.2099 | 0.060* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N11 | 0.042 (2) | 0.046 (2) | 0.0288 (17) | 0.027 (2) | 0.0031 (16) | 0.0087 (16) |
C12 | 0.051 (3) | 0.031 (2) | 0.029 (2) | 0.027 (2) | −0.0001 (19) | −0.0031 (18) |
O12 | 0.066 (2) | 0.041 (2) | 0.0378 (18) | 0.0298 (19) | 0.0025 (17) | 0.0056 (15) |
C13 | 0.056 (3) | 0.043 (3) | 0.032 (2) | 0.033 (2) | −0.006 (2) | −0.008 (2) |
N14 | 0.055 (3) | 0.049 (2) | 0.0265 (18) | 0.037 (2) | 0.0031 (17) | 0.0053 (17) |
C14 | 0.076 (4) | 0.085 (4) | 0.027 (2) | 0.060 (4) | −0.015 (2) | −0.015 (3) |
C15 | 0.046 (3) | 0.056 (3) | 0.028 (2) | 0.035 (3) | 0.0117 (19) | 0.011 (2) |
O15 | 0.062 (2) | 0.079 (3) | 0.0377 (19) | 0.045 (2) | 0.0034 (17) | 0.0206 (19) |
C16 | 0.045 (3) | 0.049 (3) | 0.038 (2) | 0.035 (2) | 0.012 (2) | 0.021 (2) |
S17 | 0.0398 (7) | 0.0447 (7) | 0.0619 (8) | 0.0213 (6) | −0.0128 (6) | 0.0003 (6) |
C18 | 0.032 (2) | 0.053 (3) | 0.068 (4) | 0.021 (2) | −0.006 (2) | −0.003 (3) |
C19 | 0.051 (3) | 0.079 (4) | 0.031 (2) | 0.037 (3) | −0.002 (2) | 0.011 (2) |
C110 | 0.046 (3) | 0.056 (3) | 0.041 (2) | 0.026 (2) | −0.007 (2) | 0.010 (2) |
C111 | 0.042 (2) | 0.031 (2) | 0.042 (3) | 0.018 (2) | −0.002 (2) | −0.003 (2) |
C112 | 0.025 (2) | 0.025 (2) | 0.039 (2) | 0.0139 (17) | 0.0039 (17) | −0.0022 (17) |
C113 | 0.026 (2) | 0.042 (3) | 0.041 (2) | 0.021 (2) | 0.0013 (18) | 0.002 (2) |
C114 | 0.034 (2) | 0.030 (2) | 0.047 (3) | 0.016 (2) | 0.0045 (19) | −0.0024 (19) |
C115 | 0.045 (3) | 0.049 (3) | 0.051 (3) | 0.028 (2) | 0.003 (2) | −0.008 (2) |
C116 | 0.045 (3) | 0.057 (3) | 0.032 (2) | 0.032 (2) | −0.001 (2) | −0.009 (2) |
C117 | 0.036 (2) | 0.033 (2) | 0.045 (3) | 0.019 (2) | 0.004 (2) | 0.0062 (19) |
N21 | 0.034 (2) | 0.035 (2) | 0.0365 (19) | 0.0214 (18) | −0.0015 (16) | 0.0008 (15) |
C22 | 0.026 (2) | 0.044 (3) | 0.029 (2) | 0.019 (2) | 0.0039 (17) | 0.0017 (18) |
O22 | 0.0287 (17) | 0.052 (2) | 0.049 (2) | 0.0214 (16) | −0.0089 (15) | −0.0032 (16) |
C23 | 0.028 (2) | 0.044 (3) | 0.036 (2) | 0.024 (2) | 0.0051 (17) | −0.0015 (19) |
N24 | 0.0333 (19) | 0.044 (2) | 0.0278 (18) | 0.0225 (18) | 0.0014 (15) | 0.0003 (16) |
C24 | 0.074 (4) | 0.054 (3) | 0.031 (2) | 0.043 (3) | 0.009 (2) | 0.004 (2) |
C25 | 0.040 (3) | 0.036 (2) | 0.038 (2) | 0.026 (2) | −0.0013 (19) | −0.0061 (19) |
O25 | 0.053 (2) | 0.049 (2) | 0.0373 (18) | 0.0278 (17) | −0.0153 (15) | −0.0084 (14) |
C26 | 0.038 (2) | 0.030 (2) | 0.034 (2) | 0.0203 (19) | −0.0046 (19) | −0.0099 (18) |
S27 | 0.0367 (6) | 0.0407 (7) | 0.0454 (6) | 0.0224 (5) | 0.0034 (5) | 0.0045 (5) |
C28 | 0.044 (3) | 0.045 (3) | 0.041 (2) | 0.026 (2) | 0.008 (2) | 0.011 (2) |
C29 | 0.063 (3) | 0.040 (3) | 0.035 (2) | 0.025 (3) | −0.009 (2) | 0.003 (2) |
C210 | 0.046 (3) | 0.045 (3) | 0.042 (3) | 0.025 (2) | −0.010 (2) | 0.001 (2) |
C211 | 0.036 (2) | 0.038 (2) | 0.038 (2) | 0.022 (2) | 0.0040 (19) | 0.0088 (19) |
C212 | 0.030 (2) | 0.030 (2) | 0.0268 (19) | 0.0176 (18) | −0.0022 (16) | −0.0043 (16) |
C213 | 0.033 (2) | 0.037 (2) | 0.030 (2) | 0.022 (2) | −0.0065 (17) | −0.0038 (18) |
C214 | 0.046 (3) | 0.031 (2) | 0.027 (2) | 0.018 (2) | 0.0025 (19) | −0.0060 (18) |
C215 | 0.035 (2) | 0.037 (2) | 0.032 (2) | 0.0213 (19) | 0.0063 (18) | −0.0047 (18) |
C216 | 0.033 (2) | 0.035 (2) | 0.034 (2) | 0.0132 (19) | −0.0074 (18) | −0.0122 (17) |
C217 | 0.031 (2) | 0.030 (2) | 0.034 (2) | 0.0182 (18) | −0.0021 (18) | 0.0016 (17) |
O1W | 0.044 (2) | 0.0407 (19) | 0.056 (2) | 0.0145 (16) | 0.0004 (17) | 0.0040 (17) |
Geometric parameters (Å, º) top
N11—C12 | 1.338 (6) | N21—C26 | 1.426 (6) |
N11—C16 | 1.431 (6) | N21—C210 | 1.482 (6) |
N11—C110 | 1.482 (6) | C22—O22 | 1.220 (6) |
C12—O12 | 1.224 (6) | C22—C23 | 1.500 (6) |
C12—C13 | 1.528 (7) | C23—N24 | 1.454 (6) |
C13—N14 | 1.465 (7) | C23—C211 | 1.549 (6) |
C13—C111 | 1.556 (7) | C23—H23 | 0.9800 |
C13—H13 | 0.9800 | N24—C25 | 1.336 (6) |
N14—C15 | 1.333 (7) | N24—C24 | 1.489 (6) |
N14—C14 | 1.479 (6) | C24—H24A | 0.9600 |
C14—H14A | 0.9600 | C24—H24B | 0.9600 |
C14—H14B | 0.9600 | C24—H24C | 0.9600 |
C14—H14C | 0.9600 | C25—O25 | 1.233 (6) |
C15—O15 | 1.253 (6) | C25—C26 | 1.524 (6) |
C15—C16 | 1.521 (6) | C26—S27 | 1.814 (5) |
C16—S17 | 1.845 (5) | C26—H26 | 0.9800 |
C16—H16 | 0.9800 | S27—C28 | 1.822 (5) |
S17—C18 | 1.805 (6) | C28—C29 | 1.518 (7) |
C18—C19 | 1.534 (8) | C28—H28A | 0.9700 |
C18—H18A | 0.9700 | C28—H28B | 0.9700 |
C18—H18B | 0.9700 | C29—C210 | 1.540 (8) |
C19—C110 | 1.478 (8) | C29—H29A | 0.9700 |
C19—H19A | 0.9700 | C29—H29B | 0.9700 |
C19—H19B | 0.9700 | C210—H21A | 0.9700 |
C110—H11A | 0.9700 | C210—H21B | 0.9700 |
C110—H11B | 0.9700 | C211—C212 | 1.500 (6) |
C111—C112 | 1.495 (6) | C211—H21C | 0.9700 |
C111—H11C | 0.9700 | C211—H21D | 0.9700 |
C111—H11D | 0.9700 | C212—C217 | 1.394 (6) |
C112—C117 | 1.385 (6) | C212—C213 | 1.398 (6) |
C112—C113 | 1.395 (6) | C213—C214 | 1.374 (6) |
C113—C114 | 1.388 (7) | C213—H213 | 0.9300 |
C113—H113 | 0.9300 | C214—C215 | 1.391 (7) |
C114—C115 | 1.395 (7) | C214—H214 | 0.9300 |
C114—H114 | 0.9300 | C215—C216 | 1.392 (6) |
C115—C116 | 1.380 (7) | C215—H215 | 0.9300 |
C115—H115 | 0.9300 | C216—C217 | 1.376 (6) |
C116—C117 | 1.408 (7) | C216—H216 | 0.9300 |
C116—H116 | 0.9300 | C217—H217 | 0.9300 |
C117—H117 | 0.9300 | O1W—H1W | 0.9138 |
N21—C22 | 1.360 (6) | O1W—H2W | 0.8308 |
| | | |
C12—N11—C16 | 124.6 (4) | C22—N21—C210 | 119.2 (4) |
C12—N11—C110 | 120.2 (4) | C26—N21—C210 | 113.5 (4) |
C16—N11—C110 | 113.6 (4) | O22—C22—N21 | 122.8 (4) |
O12—C12—N11 | 122.8 (4) | O22—C22—C23 | 119.6 (4) |
O12—C12—C13 | 118.6 (5) | N21—C22—C23 | 117.5 (4) |
N11—C12—C13 | 118.6 (4) | N24—C23—C22 | 115.6 (4) |
N14—C13—C12 | 114.4 (4) | N24—C23—C211 | 112.0 (4) |
N14—C13—C111 | 112.9 (4) | C22—C23—C211 | 109.5 (3) |
C12—C13—C111 | 108.8 (4) | N24—C23—H23 | 106.4 |
N14—C13—H13 | 106.8 | C22—C23—H23 | 106.4 |
C12—C13—H13 | 106.8 | C211—C23—H23 | 106.4 |
C111—C13—H13 | 106.8 | C25—N24—C23 | 125.2 (4) |
C15—N14—C13 | 125.8 (4) | C25—N24—C24 | 119.1 (4) |
C15—N14—C14 | 118.7 (4) | C23—N24—C24 | 115.7 (4) |
C13—N14—C14 | 115.5 (5) | N24—C24—H24A | 109.5 |
N14—C14—H14A | 109.5 | N24—C24—H24B | 109.5 |
N14—C14—H14B | 109.5 | H24A—C24—H24B | 109.5 |
H14A—C14—H14B | 109.5 | N24—C24—H24C | 109.5 |
N14—C14—H14C | 109.5 | H24A—C24—H24C | 109.5 |
H14A—C14—H14C | 109.5 | H24B—C24—H24C | 109.5 |
H14B—C14—H14C | 109.5 | O25—C25—N24 | 123.0 (4) |
O15—C15—N14 | 125.0 (4) | O25—C25—C26 | 118.6 (4) |
O15—C15—C16 | 117.2 (5) | N24—C25—C26 | 118.4 (4) |
N14—C15—C16 | 117.7 (4) | N21—C26—C25 | 113.9 (4) |
N11—C16—C15 | 115.7 (4) | N21—C26—S27 | 113.4 (3) |
N11—C16—S17 | 111.6 (3) | C25—C26—S27 | 107.1 (3) |
C15—C16—S17 | 107.1 (3) | N21—C26—H26 | 107.3 |
N11—C16—H16 | 107.4 | C25—C26—H26 | 107.3 |
C15—C16—H16 | 107.4 | S27—C26—H26 | 107.3 |
S17—C16—H16 | 107.4 | C26—S27—C28 | 95.7 (2) |
C18—S17—C16 | 96.6 (2) | C29—C28—S27 | 112.9 (4) |
C19—C18—S17 | 111.3 (4) | C29—C28—H28A | 109.0 |
C19—C18—H18A | 109.4 | S27—C28—H28A | 109.0 |
S17—C18—H18A | 109.4 | C29—C28—H28B | 109.0 |
C19—C18—H18B | 109.4 | S27—C28—H28B | 109.0 |
S17—C18—H18B | 109.4 | H28A—C28—H28B | 107.8 |
H18A—C18—H18B | 108.0 | C28—C29—C210 | 110.0 (4) |
C110—C19—C18 | 112.5 (4) | C28—C29—H29A | 109.7 |
C110—C19—H19A | 109.1 | C210—C29—H29A | 109.7 |
C18—C19—H19A | 109.1 | C28—C29—H29B | 109.7 |
C110—C19—H19B | 109.1 | C210—C29—H29B | 109.7 |
C18—C19—H19B | 109.1 | H29A—C29—H29B | 108.2 |
H19A—C19—H19B | 107.8 | N21—C210—C29 | 111.4 (4) |
C19—C110—N11 | 111.9 (4) | N21—C210—H21A | 109.3 |
C19—C110—H11A | 109.2 | C29—C210—H21A | 109.3 |
N11—C110—H11A | 109.2 | N21—C210—H21B | 109.3 |
C19—C110—H11B | 109.2 | C29—C210—H21B | 109.3 |
N11—C110—H11B | 109.2 | H21A—C210—H21B | 108.0 |
H11A—C110—H11B | 107.9 | C212—C211—C23 | 113.1 (4) |
C112—C111—C13 | 114.3 (4) | C212—C211—H21C | 109.0 |
C112—C111—H11C | 108.7 | C23—C211—H21C | 109.0 |
C13—C111—H11C | 108.7 | C212—C211—H21D | 109.0 |
C112—C111—H11D | 108.7 | C23—C211—H21D | 109.0 |
C13—C111—H11D | 108.7 | H21C—C211—H21D | 107.8 |
H11C—C111—H11D | 107.6 | C217—C212—C213 | 118.5 (4) |
C117—C112—C113 | 120.1 (4) | C217—C212—C211 | 120.4 (4) |
C117—C112—C111 | 120.2 (4) | C213—C212—C211 | 121.0 (4) |
C113—C112—C111 | 119.6 (4) | C214—C213—C212 | 120.2 (4) |
C114—C113—C112 | 120.0 (4) | C214—C213—H213 | 119.9 |
C114—C113—H113 | 120.0 | C212—C213—H213 | 119.9 |
C112—C113—H113 | 120.0 | C213—C214—C215 | 120.8 (4) |
C113—C114—C115 | 119.8 (5) | C213—C214—H214 | 119.6 |
C113—C114—H114 | 120.1 | C215—C214—H214 | 119.6 |
C115—C114—H114 | 120.1 | C214—C215—C216 | 119.3 (4) |
C116—C115—C114 | 120.4 (5) | C214—C215—H215 | 120.3 |
C116—C115—H115 | 119.8 | C216—C215—H215 | 120.3 |
C114—C115—H115 | 119.8 | C217—C216—C215 | 119.7 (4) |
C115—C116—C117 | 119.7 (4) | C217—C216—H216 | 120.2 |
C115—C116—H116 | 120.1 | C215—C216—H216 | 120.2 |
C117—C116—H116 | 120.1 | C216—C217—C212 | 121.3 (4) |
C112—C117—C116 | 119.8 (4) | C216—C217—H217 | 119.3 |
C112—C117—H117 | 120.1 | C212—C217—H217 | 119.3 |
C116—C117—H117 | 120.1 | H1W—O1W—H2W | 99.5 |
C22—N21—C26 | 125.4 (4) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W···O25i | 0.91 | 2.11 | 2.983 (5) | 159 |
O1W—H2W···O15i | 0.83 | 2.27 | 3.037 (5) | 154 |
Symmetry code: (i) x, y+1, z. |
Crystal data top
C15H18N2O2S | F(000) = 616 |
Mr = 290.37 | Dx = 1.329 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71070 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 10583 reflections |
a = 6.2287 (1) Å | θ = 1–27.5° |
b = 8.9737 (3) Å | µ = 0.23 mm−1 |
c = 25.9694 (7) Å | T = 150 K |
V = 1451.55 (7) Å3 | Bar, colourless |
Z = 4 | 0.4 × 0.25 × 0.25 mm |
Data collection top
Nonius KappaCCD area detector diffractometer | 2975 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.035 |
Graphite monochromator | θmax = 27.5°, θmin = 3.1° |
Detector resolution: 9.091 pixels mm-1 | h = −8→8 |
φ and ω scans to fill the Ewald sphere | k = −11→11 |
11349 measured reflections | l = −33→33 |
3296 independent reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.032 | w = 1/[σ2(Fo2) + (0.0234P)2 + 0.431P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.073 | (Δ/σ)max = 0.002 |
S = 1.04 | Δρmax = 0.18 e Å−3 |
3296 reflections | Δρmin = −0.23 e Å−3 |
183 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.036 (2) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.01 (6) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F2, conventional R-factors R are based
on F, with F set to zero for negative F2. The threshold expression of
F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F2 are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.4052 (2) | 0.92175 (15) | 0.68106 (5) | 0.0206 (3) | |
C2 | 0.6083 (2) | 0.91855 (18) | 0.66408 (6) | 0.0209 (3) | |
C3 | 0.6519 (3) | 0.85243 (18) | 0.61181 (6) | 0.0231 (3) | |
H3 | 0.7807 | 0.7903 | 0.6147 | 0.028* | |
N4 | 0.4801 (2) | 0.75947 (16) | 0.59111 (5) | 0.0226 (3) | |
C4 | 0.5337 (3) | 0.6728 (2) | 0.54519 (6) | 0.0311 (4) | |
H4A | 0.4379 | 0.5894 | 0.5424 | 0.047* | |
H4B | 0.6788 | 0.6375 | 0.5478 | 0.047* | |
H4C | 0.5196 | 0.7346 | 0.5152 | 0.047* | |
C5 | 0.2757 (2) | 0.76196 (18) | 0.60745 (6) | 0.0217 (3) | |
C6 | 0.2306 (2) | 0.83673 (19) | 0.65878 (6) | 0.0202 (3) | |
H6 | 0.1072 | 0.9033 | 0.6544 | 0.024* | |
S7 | 0.15137 (7) | 0.68411 (5) | 0.702119 (16) | 0.02814 (12) | |
C8 | 0.1114 (3) | 0.7946 (2) | 0.76006 (6) | 0.0290 (4) | |
H8A | −0.0153 | 0.8562 | 0.7557 | 0.035* | |
H8B | 0.0856 | 0.7282 | 0.7889 | 0.035* | |
O2 | 0.75784 (18) | 0.97884 (13) | 0.68699 (4) | 0.0280 (3) | |
O5 | 0.12814 (18) | 0.69978 (14) | 0.58448 (4) | 0.0292 (3) | |
C9 | 0.3017 (3) | 0.8936 (2) | 0.77244 (6) | 0.0268 (4) | |
H9A | 0.4264 | 0.8318 | 0.7791 | 0.032* | |
H9B | 0.2712 | 0.9500 | 0.8035 | 0.032* | |
C10 | 0.3527 (3) | 1.00125 (18) | 0.72882 (6) | 0.0242 (3) | |
H10A | 0.2299 | 1.0655 | 0.7229 | 0.029* | |
H10B | 0.4731 | 1.0636 | 0.7387 | 0.029* | |
C11 | 0.7055 (3) | 0.9840 (2) | 0.57508 (6) | 0.0291 (4) | |
H11A | 0.8363 | 1.0320 | 0.5867 | 0.035* | |
H11B | 0.7311 | 0.9452 | 0.5408 | 0.035* | |
C12 | 0.5283 (3) | 1.0979 (2) | 0.57273 (6) | 0.0271 (4) | |
C13 | 0.3553 (3) | 1.0807 (2) | 0.53912 (7) | 0.0322 (4) | |
H13 | 0.3518 | 0.9993 | 0.5169 | 0.039* | |
C14 | 0.1895 (3) | 1.1825 (2) | 0.53832 (7) | 0.0402 (5) | |
H14 | 0.0759 | 1.1696 | 0.5155 | 0.048* | |
C15 | 0.1910 (3) | 1.3029 (2) | 0.57103 (8) | 0.0438 (5) | |
H15 | 0.0786 | 1.3710 | 0.5705 | 0.053* | |
C16 | 0.3615 (4) | 1.3220 (2) | 0.60485 (7) | 0.0445 (5) | |
H16 | 0.3632 | 1.4029 | 0.6273 | 0.053* | |
C17 | 0.5288 (3) | 1.2207 (2) | 0.60510 (7) | 0.0350 (4) | |
H17 | 0.6437 | 1.2352 | 0.6274 | 0.042* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0207 (6) | 0.0218 (7) | 0.0195 (6) | −0.0001 (6) | 0.0012 (5) | −0.0019 (6) |
C2 | 0.0176 (7) | 0.0217 (8) | 0.0234 (8) | 0.0032 (6) | −0.0029 (6) | 0.0012 (7) |
C3 | 0.0161 (7) | 0.0278 (9) | 0.0253 (8) | 0.0008 (7) | 0.0011 (7) | −0.0032 (6) |
N4 | 0.0202 (6) | 0.0252 (7) | 0.0223 (7) | 0.0002 (6) | 0.0005 (5) | −0.0040 (6) |
C4 | 0.0292 (9) | 0.0361 (10) | 0.0281 (8) | 0.0005 (8) | 0.0032 (7) | −0.0104 (8) |
C5 | 0.0214 (7) | 0.0215 (8) | 0.0223 (8) | 0.0010 (6) | −0.0015 (6) | 0.0010 (7) |
C6 | 0.0158 (7) | 0.0228 (8) | 0.0219 (7) | 0.0009 (6) | −0.0005 (6) | 0.0015 (7) |
S7 | 0.0314 (2) | 0.0253 (2) | 0.0278 (2) | −0.00572 (19) | 0.00419 (18) | 0.00170 (18) |
C8 | 0.0310 (9) | 0.0327 (10) | 0.0233 (8) | 0.0001 (8) | 0.0044 (7) | 0.0046 (7) |
O2 | 0.0206 (6) | 0.0328 (7) | 0.0306 (6) | −0.0003 (5) | −0.0043 (5) | −0.0053 (5) |
O5 | 0.0226 (6) | 0.0347 (7) | 0.0302 (6) | −0.0026 (6) | −0.0042 (5) | −0.0067 (5) |
C9 | 0.0299 (9) | 0.0295 (9) | 0.0211 (8) | 0.0051 (7) | 0.0000 (7) | −0.0013 (7) |
C10 | 0.0259 (8) | 0.0234 (8) | 0.0232 (7) | −0.0001 (7) | 0.0032 (7) | −0.0049 (7) |
C11 | 0.0248 (8) | 0.0381 (10) | 0.0245 (8) | −0.0082 (8) | 0.0068 (7) | −0.0027 (8) |
C12 | 0.0322 (9) | 0.0287 (10) | 0.0205 (8) | −0.0078 (8) | 0.0035 (7) | 0.0057 (7) |
C13 | 0.0381 (10) | 0.0299 (9) | 0.0286 (9) | −0.0114 (9) | −0.0043 (8) | 0.0076 (7) |
C14 | 0.0400 (10) | 0.0381 (11) | 0.0425 (10) | −0.0099 (10) | −0.0112 (8) | 0.0165 (10) |
C15 | 0.0470 (11) | 0.0366 (11) | 0.0478 (11) | 0.0072 (10) | −0.0025 (9) | 0.0144 (10) |
C16 | 0.0671 (13) | 0.0327 (10) | 0.0339 (9) | 0.0075 (12) | −0.0062 (10) | 0.0000 (9) |
C17 | 0.0460 (11) | 0.0327 (11) | 0.0263 (9) | −0.0024 (9) | −0.0077 (8) | 0.0021 (8) |
Geometric parameters (Å, º) top
N1—C2 | 1.340 (2) | C8—H8B | 0.9700 |
N1—C6 | 1.449 (2) | C9—C10 | 1.522 (2) |
N1—C10 | 1.468 (2) | C9—H9A | 0.9700 |
C2—O2 | 1.2305 (19) | C9—H9B | 0.9700 |
C2—C3 | 1.506 (2) | C10—H10A | 0.9700 |
C3—N4 | 1.459 (2) | C10—H10B | 0.9700 |
C3—C11 | 1.554 (2) | C11—C12 | 1.505 (3) |
C3—H3 | 0.9800 | C11—H11A | 0.9700 |
N4—C5 | 1.342 (2) | C11—H11B | 0.9700 |
N4—C4 | 1.462 (2) | C12—C17 | 1.386 (3) |
C4—H4A | 0.9600 | C12—C13 | 1.395 (2) |
C4—H4B | 0.9600 | C13—C14 | 1.379 (3) |
C4—H4C | 0.9600 | C13—H13 | 0.9300 |
C5—O5 | 1.2297 (19) | C14—C15 | 1.374 (3) |
C5—C6 | 1.519 (2) | C14—H14 | 0.9300 |
C6—S7 | 1.8400 (16) | C15—C16 | 1.389 (3) |
C6—H6 | 0.9800 | C15—H15 | 0.9300 |
S7—C8 | 1.8189 (17) | C16—C17 | 1.383 (3) |
C8—C9 | 1.516 (2) | C16—H16 | 0.9300 |
C8—H8A | 0.9700 | C17—H17 | 0.9300 |
| | | |
C2—N1—C6 | 124.48 (13) | C8—C9—C10 | 112.15 (14) |
C2—N1—C10 | 119.92 (13) | C8—C9—H9A | 109.2 |
C6—N1—C10 | 115.21 (12) | C10—C9—H9A | 109.2 |
O2—C2—N1 | 123.10 (15) | C8—C9—H9B | 109.2 |
O2—C2—C3 | 118.20 (14) | C10—C9—H9B | 109.2 |
N1—C2—C3 | 118.36 (13) | H9A—C9—H9B | 107.9 |
N4—C3—C2 | 115.15 (13) | N1—C10—C9 | 111.54 (13) |
N4—C3—C11 | 111.44 (13) | N1—C10—H10A | 109.3 |
C2—C3—C11 | 107.02 (13) | C9—C10—H10A | 109.3 |
N4—C3—H3 | 107.6 | N1—C10—H10B | 109.3 |
C2—C3—H3 | 107.6 | C9—C10—H10B | 109.3 |
C11—C3—H3 | 107.6 | H10A—C10—H10B | 108.0 |
C5—N4—C3 | 124.71 (13) | C12—C11—C3 | 112.54 (13) |
C5—N4—C4 | 118.89 (14) | C12—C11—H11A | 109.1 |
C3—N4—C4 | 115.93 (13) | C3—C11—H11A | 109.1 |
N4—C4—H4A | 109.5 | C12—C11—H11B | 109.1 |
N4—C4—H4B | 109.5 | C3—C11—H11B | 109.1 |
H4A—C4—H4B | 109.5 | H11A—C11—H11B | 107.8 |
N4—C4—H4C | 109.5 | C17—C12—C13 | 117.97 (17) |
H4A—C4—H4C | 109.5 | C17—C12—C11 | 120.90 (16) |
H4B—C4—H4C | 109.5 | C13—C12—C11 | 121.10 (16) |
O5—C5—N4 | 123.24 (15) | C14—C13—C12 | 120.98 (18) |
O5—C5—C6 | 119.20 (13) | C14—C13—H13 | 119.5 |
N4—C5—C6 | 117.42 (13) | C12—C13—H13 | 119.5 |
N1—C6—C5 | 116.37 (12) | C15—C14—C13 | 120.40 (18) |
N1—C6—S7 | 110.43 (10) | C15—C14—H14 | 119.8 |
C5—C6—S7 | 104.93 (11) | C13—C14—H14 | 119.8 |
N1—C6—H6 | 108.3 | C14—C15—C16 | 119.6 (2) |
C5—C6—H6 | 108.3 | C14—C15—H15 | 120.2 |
S7—C6—H6 | 108.3 | C16—C15—H15 | 120.2 |
C8—S7—C6 | 97.88 (8) | C17—C16—C15 | 119.84 (19) |
C9—C8—S7 | 112.82 (12) | C17—C16—H16 | 120.1 |
C9—C8—H8A | 109.0 | C15—C16—H16 | 120.1 |
S7—C8—H8A | 109.0 | C16—C17—C12 | 121.22 (18) |
C9—C8—H8B | 109.0 | C16—C17—H17 | 119.4 |
S7—C8—H8B | 109.0 | C12—C17—H17 | 119.4 |
H8A—C8—H8B | 107.8 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O5i | 0.98 | 2.44 | 3.3435 (19) | 153 |
C6—H6···O2ii | 0.98 | 2.43 | 3.2916 (19) | 146 |
C8—H8A···O2ii | 0.97 | 2.53 | 3.344 (2) | 142 |
C8—H8B···O2iii | 0.97 | 2.52 | 3.253 (2) | 132 |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z; (iii) −x+1, y−1/2, −z+3/2. |
Crystal data top
C15H18N2O2S | F(000) = 616 |
Mr = 290.37 | Dx = 1.373 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71070 Å |
Hall symbol: P 2yb | Cell parameters from 28687 reflections |
a = 7.3126 (1) Å | θ = 1–27.5° |
b = 27.1077 (5) Å | µ = 0.23 mm−1 |
c = 7.3745 (1) Å | T = 150 K |
β = 106.0640 (11)° | Plate, colourless |
V = 1404.75 (4) Å3 | 0.42 × 0.42 × 0.08 mm |
Z = 4 | |
Data collection top
Nonius KappaCCD area detector diffractometer | 5572 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.032 |
Graphite monochromator | θmax = 27.4°, θmin = 2.9° |
Detector resolution: 9.091 pixels mm-1 | h = −9→9 |
φ and ω scans to fill the Ewald sphere | k = −35→34 |
22183 measured reflections | l = −9→9 |
6211 independent reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.083 | w = 1/[σ2(Fo2) + (0.0376P)2 + 0.3225P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
6211 reflections | Δρmax = 0.16 e Å−3 |
363 parameters | Δρmin = −0.22 e Å−3 |
1 restraint | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.03 (6) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F2, conventional R-factors R are based
on F, with F set to zero for negative F2. The threshold expression of
F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F2 are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.6695 (2) | 0.82534 (6) | 0.2140 (2) | 0.0204 (3) | |
C2 | 0.8202 (2) | 0.85551 (7) | 0.2369 (2) | 0.0210 (4) | |
O2 | 0.91482 (19) | 0.85832 (5) | 0.12241 (18) | 0.0309 (3) | |
C3 | 0.8767 (2) | 0.88835 (6) | 0.4094 (2) | 0.0199 (4) | |
H3 | 0.8886 | 0.9219 | 0.3641 | 0.024* | |
N4 | 0.7370 (2) | 0.89062 (5) | 0.5170 (2) | 0.0208 (3) | |
C4 | 0.7637 (3) | 0.92884 (7) | 0.6628 (3) | 0.0290 (4) | |
H4A | 0.6420 | 0.9392 | 0.6746 | 0.044* | |
H4B | 0.8284 | 0.9566 | 0.6281 | 0.044* | |
H4C | 0.8384 | 0.9158 | 0.7812 | 0.044* | |
C5 | 0.6088 (2) | 0.85508 (7) | 0.5159 (2) | 0.0213 (4) | |
O5 | 0.51521 (18) | 0.85330 (6) | 0.63010 (19) | 0.0315 (3) | |
C6 | 0.5693 (2) | 0.81742 (7) | 0.3573 (2) | 0.0208 (4) | |
H6 | 0.4332 | 0.8198 | 0.2924 | 0.025* | |
C7 | 0.6024 (3) | 0.76511 (7) | 0.4384 (3) | 0.0249 (4) | |
H7A | 0.5375 | 0.7613 | 0.5358 | 0.030* | |
H7B | 0.7374 | 0.7602 | 0.4960 | 0.030* | |
S8 | 0.51661 (8) | 0.71900 (2) | 0.25788 (7) | 0.03646 (13) | |
C9 | 0.6426 (3) | 0.74036 (8) | 0.0920 (3) | 0.0343 (5) | |
H9A | 0.7780 | 0.7351 | 0.1458 | 0.041* | |
H9B | 0.6021 | 0.7211 | −0.0230 | 0.041* | |
C10 | 0.6069 (3) | 0.79455 (7) | 0.0445 (3) | 0.0274 (4) | |
H10A | 0.6750 | 0.8042 | −0.0457 | 0.033* | |
H10B | 0.4722 | 0.7998 | −0.0136 | 0.033* | |
C11 | 1.0765 (2) | 0.87324 (7) | 0.5329 (3) | 0.0241 (4) | |
H11A | 1.1665 | 0.8762 | 0.4584 | 0.029* | |
H11B | 1.1155 | 0.8960 | 0.6380 | 0.029* | |
C12 | 1.0851 (2) | 0.82146 (7) | 0.6089 (3) | 0.0219 (4) | |
C13 | 1.1236 (2) | 0.78173 (7) | 0.5059 (3) | 0.0268 (4) | |
H13 | 1.1437 | 0.7872 | 0.3884 | 0.032* | |
C14 | 1.1325 (3) | 0.73414 (8) | 0.5757 (3) | 0.0370 (5) | |
H14 | 1.1585 | 0.7079 | 0.5054 | 0.044* | |
C15 | 1.1026 (3) | 0.72561 (8) | 0.7511 (4) | 0.0426 (6) | |
H15 | 1.1096 | 0.6937 | 0.7988 | 0.051* | |
C16 | 1.0626 (3) | 0.76446 (9) | 0.8540 (3) | 0.0393 (5) | |
H16 | 1.0416 | 0.7588 | 0.9710 | 0.047* | |
C17 | 1.0536 (3) | 0.81206 (8) | 0.7832 (3) | 0.0285 (4) | |
H17 | 1.0260 | 0.8381 | 0.8534 | 0.034* | |
N21 | 1.0345 (2) | 0.52543 (5) | 1.0909 (2) | 0.0205 (3) | |
C22 | 1.0110 (2) | 0.49609 (7) | 0.9391 (2) | 0.0211 (3) | |
O22 | 1.12701 (18) | 0.49369 (5) | 0.84587 (19) | 0.0306 (3) | |
C23 | 0.8353 (2) | 0.46406 (7) | 0.8797 (2) | 0.0203 (4) | |
H23 | 0.8792 | 0.4305 | 0.8652 | 0.024* | |
N24 | 0.7251 (2) | 0.46122 (6) | 1.0170 (2) | 0.0211 (3) | |
C24 | 0.5776 (3) | 0.42313 (7) | 0.9868 (3) | 0.0287 (4) | |
H24A | 0.5687 | 0.4111 | 1.1065 | 0.043* | |
H24B | 0.6100 | 0.3964 | 0.9161 | 0.043* | |
H24C | 0.4576 | 0.4369 | 0.9179 | 0.043* | |
C25 | 0.7300 (2) | 0.49543 (7) | 1.1490 (2) | 0.0210 (4) | |
O25 | 0.61701 (19) | 0.49628 (5) | 1.24486 (18) | 0.0313 (3) | |
C26 | 0.8884 (3) | 0.53334 (7) | 1.1898 (2) | 0.0211 (4) | |
H26 | 0.9529 | 0.5310 | 1.3250 | 0.025* | |
C27 | 0.8058 (3) | 0.58555 (7) | 1.1555 (3) | 0.0266 (4) | |
H27A | 0.7082 | 0.5895 | 1.2206 | 0.032* | |
H27B | 0.7467 | 0.5901 | 1.0216 | 0.032* | |
S28 | 0.98609 (8) | 0.632028 (19) | 1.23693 (8) | 0.03969 (15) | |
C29 | 1.1537 (3) | 0.61042 (8) | 1.1143 (3) | 0.0380 (5) | |
H29A | 1.0993 | 0.6150 | 0.9797 | 0.046* | |
H29B | 1.2688 | 0.6301 | 1.1529 | 0.046* | |
C210 | 1.2044 (3) | 0.55644 (7) | 1.1538 (3) | 0.0298 (4) | |
H21A | 1.2970 | 0.5467 | 1.0885 | 0.036* | |
H21B | 1.2612 | 0.5518 | 1.2880 | 0.036* | |
C211 | 0.7127 (3) | 0.48051 (7) | 0.6822 (2) | 0.0256 (4) | |
H21C | 0.7873 | 0.4769 | 0.5928 | 0.031* | |
H21D | 0.6037 | 0.4587 | 0.6425 | 0.031* | |
C212 | 0.6428 (3) | 0.53313 (7) | 0.6757 (2) | 0.0228 (4) | |
C213 | 0.7540 (3) | 0.57185 (7) | 0.6387 (3) | 0.0270 (4) | |
H213 | 0.8712 | 0.5649 | 0.6178 | 0.032* | |
C214 | 0.6922 (3) | 0.62023 (8) | 0.6327 (3) | 0.0334 (5) | |
H214 | 0.7675 | 0.6456 | 0.6080 | 0.040* | |
C215 | 0.5181 (3) | 0.63075 (9) | 0.6635 (3) | 0.0381 (5) | |
H215 | 0.4759 | 0.6632 | 0.6594 | 0.046* | |
C216 | 0.4071 (3) | 0.59288 (9) | 0.7004 (3) | 0.0373 (5) | |
H216 | 0.2899 | 0.5999 | 0.7207 | 0.045* | |
C217 | 0.4696 (3) | 0.54443 (8) | 0.7073 (3) | 0.0287 (4) | |
H217 | 0.3943 | 0.5193 | 0.7334 | 0.034* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0234 (7) | 0.0190 (7) | 0.0191 (7) | −0.0015 (6) | 0.0063 (6) | −0.0008 (6) |
C2 | 0.0228 (8) | 0.0184 (9) | 0.0217 (8) | 0.0007 (7) | 0.0062 (7) | 0.0019 (7) |
O2 | 0.0368 (7) | 0.0333 (8) | 0.0284 (7) | −0.0069 (6) | 0.0191 (6) | −0.0027 (6) |
C3 | 0.0193 (8) | 0.0179 (9) | 0.0241 (9) | −0.0027 (7) | 0.0084 (7) | −0.0012 (7) |
N4 | 0.0199 (7) | 0.0198 (8) | 0.0241 (8) | 0.0008 (6) | 0.0083 (6) | −0.0033 (6) |
C4 | 0.0310 (10) | 0.0252 (10) | 0.0313 (10) | 0.0022 (8) | 0.0094 (8) | −0.0084 (8) |
C5 | 0.0165 (7) | 0.0239 (9) | 0.0231 (8) | 0.0020 (7) | 0.0047 (7) | 0.0014 (7) |
O5 | 0.0248 (6) | 0.0415 (8) | 0.0327 (7) | −0.0019 (6) | 0.0154 (6) | −0.0017 (6) |
C6 | 0.0170 (8) | 0.0205 (9) | 0.0235 (9) | −0.0004 (7) | 0.0036 (7) | 0.0021 (7) |
C7 | 0.0243 (9) | 0.0241 (10) | 0.0251 (9) | −0.0023 (7) | 0.0046 (7) | 0.0035 (8) |
S8 | 0.0470 (3) | 0.0228 (3) | 0.0361 (3) | −0.0120 (2) | 0.0056 (2) | 0.0013 (2) |
C9 | 0.0483 (12) | 0.0237 (10) | 0.0310 (11) | −0.0027 (9) | 0.0113 (10) | −0.0046 (8) |
C10 | 0.0335 (10) | 0.0256 (10) | 0.0207 (9) | −0.0033 (8) | 0.0036 (8) | −0.0026 (8) |
C11 | 0.0189 (8) | 0.0232 (9) | 0.0300 (9) | −0.0029 (7) | 0.0065 (8) | −0.0010 (7) |
C12 | 0.0134 (7) | 0.0242 (9) | 0.0266 (9) | −0.0009 (7) | 0.0028 (7) | −0.0008 (7) |
C13 | 0.0174 (8) | 0.0305 (11) | 0.0315 (10) | 0.0002 (7) | 0.0052 (8) | −0.0046 (8) |
C14 | 0.0252 (9) | 0.0259 (11) | 0.0543 (14) | 0.0037 (8) | 0.0018 (9) | −0.0065 (9) |
C15 | 0.0311 (11) | 0.0302 (12) | 0.0584 (15) | −0.0021 (9) | −0.0009 (10) | 0.0160 (11) |
C16 | 0.0319 (11) | 0.0508 (14) | 0.0336 (11) | 0.0017 (10) | 0.0066 (9) | 0.0171 (10) |
C17 | 0.0214 (9) | 0.0360 (12) | 0.0268 (10) | 0.0021 (8) | 0.0046 (8) | −0.0010 (8) |
N21 | 0.0188 (7) | 0.0191 (7) | 0.0236 (7) | −0.0020 (6) | 0.0060 (6) | −0.0021 (6) |
C22 | 0.0215 (8) | 0.0182 (9) | 0.0241 (8) | 0.0004 (7) | 0.0071 (7) | 0.0016 (7) |
O22 | 0.0267 (7) | 0.0326 (8) | 0.0381 (7) | −0.0030 (6) | 0.0184 (6) | −0.0050 (6) |
C23 | 0.0218 (8) | 0.0187 (9) | 0.0213 (8) | −0.0002 (7) | 0.0079 (7) | −0.0029 (7) |
N24 | 0.0229 (7) | 0.0200 (8) | 0.0211 (7) | −0.0042 (6) | 0.0074 (6) | −0.0007 (6) |
C24 | 0.0268 (9) | 0.0270 (10) | 0.0329 (10) | −0.0082 (8) | 0.0090 (8) | 0.0004 (8) |
C25 | 0.0235 (8) | 0.0222 (9) | 0.0173 (8) | 0.0021 (7) | 0.0055 (7) | 0.0030 (7) |
O25 | 0.0331 (7) | 0.0396 (8) | 0.0260 (7) | −0.0021 (6) | 0.0162 (6) | −0.0015 (6) |
C26 | 0.0245 (9) | 0.0211 (9) | 0.0169 (8) | 0.0017 (7) | 0.0044 (7) | −0.0013 (7) |
C27 | 0.0288 (10) | 0.0225 (10) | 0.0268 (9) | 0.0040 (7) | 0.0048 (8) | −0.0021 (8) |
S28 | 0.0426 (3) | 0.0207 (3) | 0.0504 (3) | −0.0008 (2) | 0.0039 (3) | −0.0115 (2) |
C29 | 0.0370 (12) | 0.0255 (11) | 0.0501 (13) | −0.0110 (9) | 0.0093 (10) | −0.0016 (10) |
C210 | 0.0224 (9) | 0.0285 (11) | 0.0364 (11) | −0.0058 (8) | 0.0045 (8) | −0.0025 (8) |
C211 | 0.0312 (10) | 0.0280 (10) | 0.0175 (8) | −0.0028 (8) | 0.0064 (8) | −0.0042 (7) |
C212 | 0.0262 (9) | 0.0265 (10) | 0.0143 (8) | −0.0008 (7) | 0.0035 (7) | −0.0005 (7) |
C213 | 0.0293 (10) | 0.0319 (11) | 0.0216 (9) | 0.0024 (8) | 0.0101 (8) | 0.0032 (8) |
C214 | 0.0416 (12) | 0.0298 (12) | 0.0285 (10) | 0.0007 (9) | 0.0091 (9) | 0.0064 (8) |
C215 | 0.0462 (12) | 0.0328 (12) | 0.0323 (11) | 0.0135 (10) | 0.0057 (10) | 0.0049 (9) |
C216 | 0.0282 (11) | 0.0507 (14) | 0.0326 (11) | 0.0141 (10) | 0.0078 (9) | 0.0051 (10) |
C217 | 0.0241 (9) | 0.0384 (12) | 0.0224 (9) | −0.0006 (8) | 0.0045 (8) | 0.0034 (8) |
Geometric parameters (Å, º) top
N1—C2 | 1.345 (2) | N21—C22 | 1.345 (2) |
N1—C6 | 1.459 (2) | N21—C210 | 1.465 (2) |
N1—C10 | 1.467 (2) | N21—C26 | 1.467 (2) |
C2—O2 | 1.233 (2) | C22—O22 | 1.233 (2) |
C2—C3 | 1.514 (2) | C22—C23 | 1.512 (2) |
C3—N4 | 1.459 (2) | C23—N24 | 1.461 (2) |
C3—C11 | 1.547 (3) | C23—C211 | 1.549 (2) |
C3—H3 | 0.9800 | C23—H23 | 0.9800 |
N4—C5 | 1.343 (2) | N24—C25 | 1.338 (2) |
N4—C4 | 1.467 (2) | N24—C24 | 1.465 (2) |
C4—H4A | 0.9600 | C24—H24A | 0.9600 |
C4—H4B | 0.9600 | C24—H24B | 0.9600 |
C4—H4C | 0.9600 | C24—H24C | 0.9600 |
C5—O5 | 1.224 (2) | C25—O25 | 1.227 (2) |
C5—C6 | 1.519 (3) | C25—C26 | 1.515 (3) |
C6—C7 | 1.532 (3) | C26—C27 | 1.532 (3) |
C6—H6 | 0.9800 | C26—H26 | 0.9800 |
C7—S8 | 1.8072 (19) | C27—S28 | 1.802 (2) |
C7—H7A | 0.9700 | C27—H27A | 0.9700 |
C7—H7B | 0.9700 | C27—H27B | 0.9700 |
S8—C9 | 1.817 (2) | S28—C29 | 1.810 (2) |
C9—C10 | 1.516 (3) | C29—C210 | 1.518 (3) |
C9—H9A | 0.9700 | C29—H29A | 0.9700 |
C9—H9B | 0.9700 | C29—H29B | 0.9700 |
C10—H10A | 0.9700 | C210—H21A | 0.9700 |
C10—H10B | 0.9700 | C210—H21B | 0.9700 |
C11—C12 | 1.506 (3) | C211—C212 | 1.512 (3) |
C11—H11A | 0.9700 | C211—H21C | 0.9700 |
C11—H11B | 0.9700 | C211—H21D | 0.9700 |
C12—C17 | 1.391 (3) | C212—C217 | 1.384 (3) |
C12—C13 | 1.391 (3) | C212—C213 | 1.400 (3) |
C13—C14 | 1.384 (3) | C213—C214 | 1.384 (3) |
C13—H13 | 0.9300 | C213—H213 | 0.9300 |
C14—C15 | 1.389 (4) | C214—C215 | 1.384 (3) |
C14—H14 | 0.9300 | C214—H214 | 0.9300 |
C15—C16 | 1.376 (4) | C215—C216 | 1.381 (3) |
C15—H15 | 0.9300 | C215—H215 | 0.9300 |
C16—C17 | 1.387 (3) | C216—C217 | 1.387 (3) |
C16—H16 | 0.9300 | C216—H216 | 0.9300 |
C17—H17 | 0.9300 | C217—H217 | 0.9300 |
| | | |
C2—N1—C6 | 123.85 (14) | C22—N21—C210 | 120.33 (15) |
C2—N1—C10 | 120.27 (15) | C22—N21—C26 | 123.87 (14) |
C6—N1—C10 | 115.66 (14) | C210—N21—C26 | 115.43 (14) |
O2—C2—N1 | 123.18 (16) | O22—C22—N21 | 123.10 (16) |
O2—C2—C3 | 117.70 (15) | O22—C22—C23 | 117.95 (15) |
N1—C2—C3 | 119.12 (14) | N21—C22—C23 | 118.94 (14) |
N4—C3—C2 | 114.38 (14) | N24—C23—C22 | 114.64 (14) |
N4—C3—C11 | 112.35 (14) | N24—C23—C211 | 112.34 (14) |
C2—C3—C11 | 109.43 (14) | C22—C23—C211 | 109.38 (15) |
N4—C3—H3 | 106.7 | N24—C23—H23 | 106.7 |
C2—C3—H3 | 106.7 | C22—C23—H23 | 106.7 |
C11—C3—H3 | 106.7 | C211—C23—H23 | 106.7 |
C5—N4—C3 | 124.02 (14) | C25—N24—C23 | 124.01 (14) |
C5—N4—C4 | 117.57 (15) | C25—N24—C24 | 118.03 (15) |
C3—N4—C4 | 117.21 (14) | C23—N24—C24 | 117.11 (14) |
N4—C4—H4A | 109.5 | N24—C24—H24A | 109.5 |
N4—C4—H4B | 109.5 | N24—C24—H24B | 109.5 |
H4A—C4—H4B | 109.5 | H24A—C24—H24B | 109.5 |
N4—C4—H4C | 109.5 | N24—C24—H24C | 109.5 |
H4A—C4—H4C | 109.5 | H24A—C24—H24C | 109.5 |
H4B—C4—H4C | 109.5 | H24B—C24—H24C | 109.5 |
O5—C5—N4 | 123.10 (17) | O25—C25—N24 | 123.05 (16) |
O5—C5—C6 | 118.68 (15) | O25—C25—C26 | 118.20 (15) |
N4—C5—C6 | 118.10 (14) | N24—C25—C26 | 118.67 (14) |
N1—C6—C5 | 115.62 (14) | N21—C26—C25 | 115.12 (14) |
N1—C6—C7 | 111.25 (14) | N21—C26—C27 | 111.14 (15) |
C5—C6—C7 | 110.23 (14) | C25—C26—C27 | 110.45 (14) |
N1—C6—H6 | 106.4 | N21—C26—H26 | 106.5 |
C5—C6—H6 | 106.4 | C25—C26—H26 | 106.5 |
C7—C6—H6 | 106.4 | C27—C26—H26 | 106.5 |
C6—C7—S8 | 111.56 (12) | C26—C27—S28 | 111.88 (13) |
C6—C7—H7A | 109.3 | C26—C27—H27A | 109.2 |
S8—C7—H7A | 109.3 | S28—C27—H27A | 109.2 |
C6—C7—H7B | 109.3 | C26—C27—H27B | 109.2 |
S8—C7—H7B | 109.3 | S28—C27—H27B | 109.2 |
H7A—C7—H7B | 108.0 | H27A—C27—H27B | 107.9 |
C7—S8—C9 | 97.94 (9) | C27—S28—C29 | 98.12 (9) |
C10—C9—S8 | 112.20 (15) | C210—C29—S28 | 112.30 (16) |
C10—C9—H9A | 109.2 | C210—C29—H29A | 109.1 |
S8—C9—H9A | 109.2 | S28—C29—H29A | 109.1 |
C10—C9—H9B | 109.2 | C210—C29—H29B | 109.1 |
S8—C9—H9B | 109.2 | S28—C29—H29B | 109.1 |
H9A—C9—H9B | 107.9 | H29A—C29—H29B | 107.9 |
N1—C10—C9 | 111.16 (16) | N21—C210—C29 | 110.59 (16) |
N1—C10—H10A | 109.4 | N21—C210—H21A | 109.5 |
C9—C10—H10A | 109.4 | C29—C210—H21A | 109.5 |
N1—C10—H10B | 109.4 | N21—C210—H21B | 109.5 |
C9—C10—H10B | 109.4 | C29—C210—H21B | 109.5 |
H10A—C10—H10B | 108.0 | H21A—C210—H21B | 108.1 |
C12—C11—C3 | 113.65 (14) | C212—C211—C23 | 113.86 (14) |
C12—C11—H11A | 108.8 | C212—C211—H21C | 108.8 |
C3—C11—H11A | 108.8 | C23—C211—H21C | 108.8 |
C12—C11—H11B | 108.8 | C212—C211—H21D | 108.8 |
C3—C11—H11B | 108.8 | C23—C211—H21D | 108.8 |
H11A—C11—H11B | 107.7 | H21C—C211—H21D | 107.7 |
C17—C12—C13 | 118.23 (18) | C217—C212—C213 | 118.36 (18) |
C17—C12—C11 | 120.96 (17) | C217—C212—C211 | 121.38 (18) |
C13—C12—C11 | 120.80 (17) | C213—C212—C211 | 120.25 (17) |
C14—C13—C12 | 120.97 (19) | C214—C213—C212 | 120.95 (18) |
C14—C13—H13 | 119.5 | C214—C213—H213 | 119.5 |
C12—C13—H13 | 119.5 | C212—C213—H213 | 119.5 |
C13—C14—C15 | 119.9 (2) | C215—C214—C213 | 119.8 (2) |
C13—C14—H14 | 120.1 | C215—C214—H214 | 120.1 |
C15—C14—H14 | 120.1 | C213—C214—H214 | 120.1 |
C16—C15—C14 | 119.9 (2) | C216—C215—C214 | 119.8 (2) |
C16—C15—H15 | 120.1 | C216—C215—H215 | 120.1 |
C14—C15—H15 | 120.1 | C214—C215—H215 | 120.1 |
C15—C16—C17 | 120.0 (2) | C215—C216—C217 | 120.37 (19) |
C15—C16—H16 | 120.0 | C215—C216—H216 | 119.8 |
C17—C16—H16 | 120.0 | C217—C216—H216 | 119.8 |
C16—C17—C12 | 121.0 (2) | C212—C217—C216 | 120.7 (2) |
C16—C17—H17 | 119.5 | C212—C217—H217 | 119.6 |
C12—C17—H17 | 119.5 | C216—C217—H217 | 119.6 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O22i | 0.98 | 2.47 | 3.416 (2) | 162 |
C11—H11A···O5ii | 0.97 | 2.59 | 3.135 (2) | 116 |
C17—H17···O2iii | 0.93 | 2.41 | 3.204 (2) | 144 |
C211—H21C···O25iv | 0.97 | 2.58 | 3.135 (2) | 117 |
C23—H23···O2v | 0.98 | 2.46 | 3.402 (2) | 162 |
C217—H217···O22vi | 0.93 | 2.43 | 3.260 (2) | 149 |
Symmetry codes: (i) −x+2, y+1/2, −z+1; (ii) x+1, y, z; (iii) x, y, z+1; (iv) x, y, z−1; (v) −x+2, y−1/2, −z+1; (vi) x−1, y, z. |
Crystal data top
C15H18N2O2S | F(000) = 616 |
Mr = 290.37 | Dx = 1.325 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71070 Å |
Hall symbol: P 2yb | Cell parameters from 16855 reflections |
a = 9.8928 (2) Å | θ = 1–27.5° |
b = 9.0312 (2) Å | µ = 0.23 mm−1 |
c = 16.4470 (5) Å | T = 150 K |
β = 97.8246 (15)° | Bar, colourless |
V = 1455.76 (6) Å3 | 0.5 × 0.15 × 0.1 mm |
Z = 4 | |
Data collection top
Nonius KappaCCD area detector diffractometer | 5781 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.045 |
Graphite monochromator | θmax = 27.5°, θmin = 3.2° |
Detector resolution: 9.091 pixels mm-1 | h = −12→12 |
φ and ω scans to fill the Ewald sphere | k = −11→11 |
23095 measured reflections | l = −21→21 |
6621 independent reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.082 | w = 1/[σ2(Fo2) + (0.0316P)2 + 0.3753P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
6621 reflections | Δρmax = 0.22 e Å−3 |
363 parameters | Δρmin = −0.22 e Å−3 |
1 restraint | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.06 (5) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F2, conventional R-factors R are based
on F, with F set to zero for negative F2. The threshold expression of
F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F2 are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.26974 (15) | 0.09585 (17) | 0.37766 (9) | 0.0226 (3) | |
C2 | 0.36775 (19) | 0.04534 (19) | 0.33489 (11) | 0.0231 (4) | |
O2 | 0.34415 (14) | −0.03944 (14) | 0.27615 (8) | 0.0323 (3) | |
C3 | 0.51233 (19) | 0.0982 (2) | 0.35878 (12) | 0.0248 (4) | |
H3 | 0.5720 | 0.0112 | 0.3610 | 0.030* | |
N4 | 0.53693 (14) | 0.17062 (17) | 0.43830 (9) | 0.0237 (3) | |
C4 | 0.67909 (19) | 0.1838 (3) | 0.47573 (13) | 0.0359 (5) | |
H4A | 0.7204 | 0.2671 | 0.4525 | 0.054* | |
H4B | 0.7276 | 0.0951 | 0.4655 | 0.054* | |
H4C | 0.6827 | 0.1979 | 0.5338 | 0.054* | |
C5 | 0.44075 (19) | 0.24650 (19) | 0.47023 (11) | 0.0236 (4) | |
O5 | 0.46557 (13) | 0.33206 (15) | 0.52862 (8) | 0.0319 (3) | |
C6 | 0.29172 (18) | 0.21877 (19) | 0.43574 (11) | 0.0222 (4) | |
H6 | 0.2552 | 0.3090 | 0.4079 | 0.027* | |
C7 | 0.21595 (18) | 0.1919 (2) | 0.50931 (12) | 0.0302 (4) | |
H7A | 0.2340 | 0.2737 | 0.5474 | 0.036* | |
H7B | 0.2513 | 0.1026 | 0.5373 | 0.036* | |
S8 | 0.03443 (5) | 0.17300 (7) | 0.48181 (3) | 0.03746 (13) | |
C9 | 0.0414 (2) | 0.0221 (2) | 0.41060 (13) | 0.0341 (5) | |
H9A | 0.0791 | −0.0646 | 0.4402 | 0.041* | |
H9B | −0.0504 | −0.0018 | 0.3853 | 0.041* | |
C10 | 0.12734 (19) | 0.0608 (2) | 0.34480 (12) | 0.0303 (4) | |
H10A | 0.1264 | −0.0218 | 0.3070 | 0.036* | |
H10B | 0.0872 | 0.1453 | 0.3141 | 0.036* | |
C11 | 0.54995 (19) | 0.2002 (2) | 0.28941 (12) | 0.0281 (4) | |
H11A | 0.6460 | 0.2251 | 0.3008 | 0.034* | |
H11B | 0.5360 | 0.1462 | 0.2380 | 0.034* | |
C12 | 0.46810 (18) | 0.3411 (2) | 0.27977 (11) | 0.0258 (4) | |
C13 | 0.5105 (2) | 0.4683 (2) | 0.32414 (12) | 0.0290 (4) | |
H13 | 0.5908 | 0.4660 | 0.3609 | 0.035* | |
C14 | 0.4355 (2) | 0.5978 (2) | 0.31452 (13) | 0.0319 (4) | |
H14 | 0.4660 | 0.6818 | 0.3442 | 0.038* | |
C15 | 0.3155 (2) | 0.6026 (2) | 0.26090 (13) | 0.0328 (5) | |
H15 | 0.2649 | 0.6896 | 0.2544 | 0.039* | |
C16 | 0.2707 (2) | 0.4774 (2) | 0.21691 (14) | 0.0354 (5) | |
H16 | 0.1891 | 0.4797 | 0.1814 | 0.042* | |
C17 | 0.34728 (19) | 0.3483 (2) | 0.22556 (12) | 0.0298 (4) | |
H17 | 0.3175 | 0.2654 | 0.1947 | 0.036* | |
N21 | 0.79215 (15) | 0.66563 (17) | 0.22461 (9) | 0.0244 (3) | |
C22 | 0.73000 (18) | 0.7944 (2) | 0.23921 (11) | 0.0229 (4) | |
O22 | 0.76346 (13) | 0.87162 (14) | 0.29992 (8) | 0.0300 (3) | |
C23 | 0.61717 (17) | 0.8489 (2) | 0.17468 (10) | 0.0225 (4) | |
H23 | 0.5458 | 0.8911 | 0.2035 | 0.027* | |
N24 | 0.55451 (16) | 0.73322 (16) | 0.12097 (9) | 0.0253 (3) | |
C24 | 0.4176 (2) | 0.7611 (2) | 0.07789 (14) | 0.0361 (5) | |
H24A | 0.4244 | 0.8041 | 0.0252 | 0.054* | |
H24B | 0.3703 | 0.8280 | 0.1095 | 0.054* | |
H24C | 0.3683 | 0.6694 | 0.0706 | 0.054* | |
C25 | 0.6247 (2) | 0.6169 (2) | 0.09895 (12) | 0.0305 (4) | |
O25 | 0.57947 (18) | 0.53368 (18) | 0.04268 (10) | 0.0502 (4) | |
C26 | 0.76157 (19) | 0.5811 (2) | 0.14838 (11) | 0.0250 (4) | |
H26 | 0.8334 | 0.6001 | 0.1142 | 0.030* | |
C27 | 0.7582 (2) | 0.4150 (2) | 0.16631 (13) | 0.0292 (4) | |
H27A | 0.7385 | 0.3623 | 0.1147 | 0.035* | |
H27B | 0.6841 | 0.3954 | 0.1979 | 0.035* | |
S28 | 0.91319 (6) | 0.34311 (6) | 0.22139 (3) | 0.03858 (14) | |
C29 | 0.9283 (2) | 0.4728 (2) | 0.30545 (13) | 0.0379 (5) | |
H29A | 0.8550 | 0.4558 | 0.3380 | 0.046* | |
H29B | 1.0141 | 0.4563 | 0.3404 | 0.046* | |
C210 | 0.9224 (2) | 0.6310 (2) | 0.27577 (13) | 0.0318 (5) | |
H21A | 0.9345 | 0.6969 | 0.3228 | 0.038* | |
H21B | 0.9968 | 0.6484 | 0.2442 | 0.038* | |
C211 | 0.67422 (19) | 0.9770 (2) | 0.12559 (12) | 0.0257 (4) | |
H21C | 0.6033 | 1.0106 | 0.0830 | 0.031* | |
H21D | 0.6992 | 1.0596 | 0.1623 | 0.031* | |
C212 | 0.7969 (2) | 0.9300 (2) | 0.08679 (12) | 0.0271 (4) | |
C213 | 0.7833 (2) | 0.8635 (2) | 0.00970 (12) | 0.0344 (5) | |
H213 | 0.6976 | 0.8564 | −0.0213 | 0.041* | |
C214 | 0.8968 (3) | 0.8079 (3) | −0.02118 (14) | 0.0482 (6) | |
H214 | 0.8865 | 0.7609 | −0.0720 | 0.058* | |
C215 | 1.0254 (3) | 0.8222 (3) | 0.02349 (15) | 0.0580 (7) | |
H215 | 1.1014 | 0.7853 | 0.0026 | 0.070* | |
C216 | 1.0402 (2) | 0.8911 (3) | 0.09866 (15) | 0.0495 (7) | |
H216 | 1.1265 | 0.9015 | 0.1285 | 0.059* | |
C217 | 0.9277 (2) | 0.9447 (2) | 0.12983 (13) | 0.0359 (5) | |
H217 | 0.9390 | 0.9916 | 0.1806 | 0.043* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0204 (7) | 0.0213 (7) | 0.0257 (8) | 0.0002 (6) | 0.0012 (6) | −0.0042 (6) |
C2 | 0.0299 (10) | 0.0158 (8) | 0.0240 (9) | 0.0038 (7) | 0.0053 (8) | 0.0024 (7) |
O2 | 0.0402 (8) | 0.0252 (7) | 0.0327 (7) | −0.0007 (6) | 0.0095 (6) | −0.0085 (6) |
C3 | 0.0262 (9) | 0.0177 (8) | 0.0318 (10) | 0.0035 (8) | 0.0083 (8) | 0.0018 (8) |
N4 | 0.0182 (7) | 0.0239 (7) | 0.0286 (8) | 0.0015 (7) | 0.0018 (6) | 0.0003 (7) |
C4 | 0.0207 (9) | 0.0415 (11) | 0.0450 (12) | 0.0004 (9) | 0.0020 (9) | 0.0040 (11) |
C5 | 0.0258 (9) | 0.0193 (9) | 0.0254 (9) | −0.0004 (7) | 0.0030 (8) | 0.0015 (8) |
O5 | 0.0317 (7) | 0.0316 (7) | 0.0311 (7) | −0.0041 (6) | −0.0002 (6) | −0.0095 (6) |
C6 | 0.0227 (9) | 0.0195 (9) | 0.0240 (9) | 0.0024 (7) | 0.0017 (7) | −0.0013 (7) |
C7 | 0.0244 (9) | 0.0397 (11) | 0.0261 (9) | −0.0019 (9) | 0.0022 (8) | −0.0048 (9) |
S8 | 0.0222 (2) | 0.0525 (3) | 0.0387 (3) | 0.0000 (2) | 0.0078 (2) | −0.0081 (3) |
C9 | 0.0221 (10) | 0.0367 (11) | 0.0426 (12) | −0.0052 (9) | 0.0013 (9) | −0.0015 (10) |
C10 | 0.0245 (10) | 0.0338 (11) | 0.0307 (11) | 0.0006 (8) | −0.0037 (8) | −0.0057 (9) |
C11 | 0.0289 (10) | 0.0236 (9) | 0.0343 (11) | 0.0002 (8) | 0.0128 (8) | 0.0012 (8) |
C12 | 0.0299 (10) | 0.0225 (8) | 0.0274 (9) | −0.0021 (8) | 0.0125 (8) | 0.0029 (8) |
C13 | 0.0288 (10) | 0.0257 (10) | 0.0317 (10) | −0.0031 (8) | 0.0016 (8) | 0.0000 (8) |
C14 | 0.0385 (12) | 0.0217 (9) | 0.0369 (11) | −0.0029 (9) | 0.0096 (9) | −0.0035 (9) |
C15 | 0.0366 (11) | 0.0221 (9) | 0.0408 (12) | 0.0054 (9) | 0.0089 (9) | 0.0027 (9) |
C16 | 0.0317 (11) | 0.0312 (11) | 0.0413 (12) | 0.0014 (9) | −0.0024 (9) | 0.0012 (9) |
C17 | 0.0365 (11) | 0.0218 (9) | 0.0305 (10) | −0.0045 (9) | 0.0026 (8) | −0.0038 (9) |
N21 | 0.0256 (8) | 0.0240 (8) | 0.0227 (8) | 0.0044 (7) | −0.0002 (6) | 0.0000 (7) |
C22 | 0.0228 (9) | 0.0235 (9) | 0.0232 (10) | −0.0017 (7) | 0.0057 (8) | 0.0006 (7) |
O22 | 0.0350 (7) | 0.0298 (7) | 0.0249 (7) | 0.0010 (6) | 0.0030 (6) | −0.0064 (6) |
C23 | 0.0231 (9) | 0.0220 (8) | 0.0226 (9) | 0.0023 (8) | 0.0035 (7) | −0.0037 (8) |
N24 | 0.0229 (8) | 0.0252 (8) | 0.0264 (8) | 0.0000 (6) | −0.0013 (6) | −0.0012 (7) |
C24 | 0.0279 (11) | 0.0348 (11) | 0.0421 (12) | −0.0006 (9) | −0.0085 (9) | 0.0054 (10) |
C25 | 0.0362 (11) | 0.0246 (10) | 0.0287 (10) | 0.0011 (9) | −0.0026 (9) | −0.0016 (8) |
O25 | 0.0594 (11) | 0.0387 (9) | 0.0449 (9) | 0.0107 (8) | −0.0198 (8) | −0.0166 (8) |
C26 | 0.0297 (10) | 0.0223 (9) | 0.0231 (9) | 0.0024 (8) | 0.0041 (8) | −0.0028 (7) |
C27 | 0.0301 (11) | 0.0236 (9) | 0.0342 (11) | 0.0033 (8) | 0.0060 (9) | −0.0016 (8) |
S28 | 0.0402 (3) | 0.0279 (3) | 0.0460 (3) | 0.0122 (2) | −0.0001 (2) | 0.0018 (2) |
C29 | 0.0387 (12) | 0.0391 (12) | 0.0336 (11) | 0.0105 (10) | −0.0036 (9) | 0.0036 (10) |
C210 | 0.0294 (10) | 0.0343 (11) | 0.0294 (10) | 0.0036 (8) | −0.0047 (8) | −0.0006 (9) |
C211 | 0.0264 (10) | 0.0218 (9) | 0.0288 (10) | 0.0024 (8) | 0.0034 (8) | 0.0016 (8) |
C212 | 0.0279 (10) | 0.0257 (10) | 0.0280 (10) | 0.0018 (8) | 0.0049 (8) | 0.0063 (8) |
C213 | 0.0359 (11) | 0.0400 (12) | 0.0277 (10) | 0.0054 (10) | 0.0060 (9) | 0.0076 (9) |
C214 | 0.0573 (15) | 0.0616 (16) | 0.0282 (11) | 0.0189 (12) | 0.0152 (11) | 0.0072 (11) |
C215 | 0.0452 (14) | 0.087 (2) | 0.0476 (15) | 0.0241 (14) | 0.0260 (12) | 0.0161 (14) |
C216 | 0.0277 (12) | 0.0770 (18) | 0.0451 (14) | 0.0060 (11) | 0.0094 (10) | 0.0129 (13) |
C217 | 0.0317 (11) | 0.0435 (12) | 0.0333 (11) | −0.0028 (9) | 0.0066 (9) | 0.0048 (10) |
Geometric parameters (Å, º) top
N1—C2 | 1.352 (2) | N21—C22 | 1.352 (2) |
N1—C6 | 1.461 (2) | N21—C26 | 1.464 (2) |
N1—C10 | 1.473 (2) | N21—C210 | 1.473 (2) |
C2—O2 | 1.230 (2) | C22—O22 | 1.226 (2) |
C2—C3 | 1.508 (3) | C22—C23 | 1.514 (2) |
C3—N4 | 1.453 (2) | C23—N24 | 1.452 (2) |
C3—C11 | 1.551 (3) | C23—C211 | 1.560 (3) |
C3—H3 | 0.9800 | C23—H23 | 0.9800 |
N4—C5 | 1.337 (2) | N24—C25 | 1.336 (2) |
N4—C4 | 1.461 (2) | N24—C24 | 1.462 (2) |
C4—H4A | 0.9600 | C24—H24A | 0.9600 |
C4—H4B | 0.9600 | C24—H24B | 0.9600 |
C4—H4C | 0.9600 | C24—H24C | 0.9600 |
C5—O5 | 1.231 (2) | C25—O25 | 1.228 (2) |
C5—C6 | 1.527 (2) | C25—C26 | 1.517 (3) |
C6—C7 | 1.527 (3) | C26—C27 | 1.530 (3) |
C6—H6 | 0.9800 | C26—H26 | 0.9800 |
C7—S8 | 1.7992 (18) | C27—S28 | 1.793 (2) |
C7—H7A | 0.9700 | C27—H27A | 0.9700 |
C7—H7B | 0.9700 | C27—H27B | 0.9700 |
S8—C9 | 1.804 (2) | S28—C29 | 1.803 (2) |
C9—C10 | 1.506 (3) | C29—C210 | 1.508 (3) |
C9—H9A | 0.9700 | C29—H29A | 0.9700 |
C9—H9B | 0.9700 | C29—H29B | 0.9700 |
C10—H10A | 0.9700 | C210—H21A | 0.9700 |
C10—H10B | 0.9700 | C210—H21B | 0.9700 |
C11—C12 | 1.505 (3) | C211—C212 | 1.507 (3) |
C11—H11A | 0.9700 | C211—H21C | 0.9700 |
C11—H11B | 0.9700 | C211—H21D | 0.9700 |
C12—C17 | 1.392 (3) | C212—C213 | 1.393 (3) |
C12—C13 | 1.395 (3) | C212—C217 | 1.394 (3) |
C13—C14 | 1.382 (3) | C213—C214 | 1.388 (3) |
C13—H13 | 0.9300 | C213—H213 | 0.9300 |
C14—C15 | 1.380 (3) | C214—C215 | 1.385 (4) |
C14—H14 | 0.9300 | C214—H214 | 0.9300 |
C15—C16 | 1.382 (3) | C215—C216 | 1.374 (4) |
C15—H15 | 0.9300 | C215—H215 | 0.9300 |
C16—C17 | 1.387 (3) | C216—C217 | 1.376 (3) |
C16—H16 | 0.9300 | C216—H216 | 0.9300 |
C17—H17 | 0.9300 | C217—H217 | 0.9300 |
| | | |
C2—N1—C6 | 122.88 (15) | C22—N21—C26 | 123.69 (15) |
C2—N1—C10 | 117.02 (15) | C22—N21—C210 | 117.69 (15) |
C6—N1—C10 | 116.93 (14) | C26—N21—C210 | 116.17 (15) |
O2—C2—N1 | 123.08 (17) | O22—C22—N21 | 123.71 (16) |
O2—C2—C3 | 118.27 (16) | O22—C22—C23 | 118.54 (16) |
N1—C2—C3 | 118.64 (15) | N21—C22—C23 | 117.69 (15) |
N4—C3—C2 | 114.44 (15) | N24—C23—C22 | 113.92 (15) |
N4—C3—C11 | 111.56 (15) | N24—C23—C211 | 111.94 (14) |
C2—C3—C11 | 108.08 (15) | C22—C23—C211 | 108.65 (15) |
N4—C3—H3 | 107.5 | N24—C23—H23 | 107.3 |
C2—C3—H3 | 107.5 | C22—C23—H23 | 107.3 |
C11—C3—H3 | 107.5 | C211—C23—H23 | 107.3 |
C5—N4—C3 | 122.92 (14) | C25—N24—C23 | 122.44 (15) |
C5—N4—C4 | 119.24 (16) | C25—N24—C24 | 119.01 (16) |
C3—N4—C4 | 116.72 (15) | C23—N24—C24 | 117.49 (15) |
N4—C4—H4A | 109.5 | N24—C24—H24A | 109.5 |
N4—C4—H4B | 109.5 | N24—C24—H24B | 109.5 |
H4A—C4—H4B | 109.5 | H24A—C24—H24B | 109.5 |
N4—C4—H4C | 109.5 | N24—C24—H24C | 109.5 |
H4A—C4—H4C | 109.5 | H24A—C24—H24C | 109.5 |
H4B—C4—H4C | 109.5 | H24B—C24—H24C | 109.5 |
O5—C5—N4 | 123.45 (17) | O25—C25—N24 | 122.42 (18) |
O5—C5—C6 | 118.22 (16) | O25—C25—C26 | 118.71 (17) |
N4—C5—C6 | 118.23 (15) | N24—C25—C26 | 118.77 (16) |
N1—C6—C5 | 114.69 (14) | N21—C26—C25 | 114.41 (15) |
N1—C6—C7 | 110.59 (15) | N21—C26—C27 | 110.71 (15) |
C5—C6—C7 | 106.56 (14) | C25—C26—C27 | 105.71 (15) |
N1—C6—H6 | 108.3 | N21—C26—H26 | 108.6 |
C5—C6—H6 | 108.3 | C25—C26—H26 | 108.6 |
C7—C6—H6 | 108.3 | C27—C26—H26 | 108.6 |
C6—C7—S8 | 113.37 (13) | C26—C27—S28 | 114.37 (14) |
C6—C7—H7A | 108.9 | C26—C27—H27A | 108.7 |
S8—C7—H7A | 108.9 | S28—C27—H27A | 108.7 |
C6—C7—H7B | 108.9 | C26—C27—H27B | 108.7 |
S8—C7—H7B | 108.9 | S28—C27—H27B | 108.7 |
H7A—C7—H7B | 107.7 | H27A—C27—H27B | 107.6 |
C7—S8—C9 | 96.30 (9) | C27—S28—C29 | 97.35 (9) |
C10—C9—S8 | 111.52 (14) | C210—C29—S28 | 111.83 (15) |
C10—C9—H9A | 109.3 | C210—C29—H29A | 109.3 |
S8—C9—H9A | 109.3 | S28—C29—H29A | 109.3 |
C10—C9—H9B | 109.3 | C210—C29—H29B | 109.3 |
S8—C9—H9B | 109.3 | S28—C29—H29B | 109.3 |
H9A—C9—H9B | 108.0 | H29A—C29—H29B | 107.9 |
N1—C10—C9 | 113.06 (16) | N21—C210—C29 | 112.23 (17) |
N1—C10—H10A | 109.0 | N21—C210—H21A | 109.2 |
C9—C10—H10A | 109.0 | C29—C210—H21A | 109.2 |
N1—C10—H10B | 109.0 | N21—C210—H21B | 109.2 |
C9—C10—H10B | 109.0 | C29—C210—H21B | 109.2 |
H10A—C10—H10B | 107.8 | H21A—C210—H21B | 107.9 |
C12—C11—C3 | 113.59 (15) | C212—C211—C23 | 112.29 (15) |
C12—C11—H11A | 108.8 | C212—C211—H21C | 109.1 |
C3—C11—H11A | 108.8 | C23—C211—H21C | 109.1 |
C12—C11—H11B | 108.8 | C212—C211—H21D | 109.1 |
C3—C11—H11B | 108.8 | C23—C211—H21D | 109.1 |
H11A—C11—H11B | 107.7 | H21C—C211—H21D | 107.9 |
C17—C12—C13 | 117.87 (18) | C213—C212—C217 | 118.12 (19) |
C17—C12—C11 | 120.65 (18) | C213—C212—C211 | 121.54 (17) |
C13—C12—C11 | 121.48 (17) | C217—C212—C211 | 120.24 (18) |
C14—C13—C12 | 121.23 (18) | C214—C213—C212 | 120.4 (2) |
C14—C13—H13 | 119.4 | C214—C213—H213 | 119.8 |
C12—C13—H13 | 119.4 | C212—C213—H213 | 119.8 |
C15—C14—C13 | 120.08 (19) | C215—C214—C213 | 120.2 (2) |
C15—C14—H14 | 120.0 | C215—C214—H214 | 119.9 |
C13—C14—H14 | 120.0 | C213—C214—H214 | 119.9 |
C14—C15—C16 | 119.70 (19) | C216—C215—C214 | 119.8 (2) |
C14—C15—H15 | 120.2 | C216—C215—H215 | 120.1 |
C16—C15—H15 | 120.2 | C214—C215—H215 | 120.1 |
C15—C16—C17 | 120.14 (18) | C215—C216—C217 | 120.1 (2) |
C15—C16—H16 | 119.9 | C215—C216—H216 | 120.0 |
C17—C16—H16 | 119.9 | C217—C216—H216 | 120.0 |
C16—C17—C12 | 120.96 (18) | C216—C217—C212 | 121.3 (2) |
C16—C17—H17 | 119.5 | C216—C217—H217 | 119.3 |
C12—C17—H17 | 119.5 | C212—C217—H217 | 119.3 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O22i | 0.98 | 2.59 | 3.457 (2) | 148 |
C3—H3···O5ii | 0.98 | 2.50 | 3.024 (2) | 114 |
C9—H9B···O22iii | 0.97 | 2.44 | 3.370 (2) | 160 |
C10—H10B···S28iv | 0.97 | 2.79 | 3.733 (2) | 166 |
C15—H15···O2v | 0.93 | 2.58 | 3.252 (2) | 130 |
C211—H21C···O25vi | 0.97 | 2.56 | 3.511 (2) | 166 |
C23—H23···O2v | 0.98 | 2.54 | 3.511 (2) | 171 |
C24—H24A···O25vi | 0.96 | 2.35 | 3.164 (3) | 142 |
C14—H14···O5vii | 0.93 | 2.51 | 3.377 (2) | 156 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, y−1/2, −z+1; (iii) x−1, y−1, z; (iv) x−1, y, z; (v) x, y+1, z; (vi) −x+1, y+1/2, −z; (vii) −x+1, y+1/2, −z+1. |
Crystal data top
C15H18N2O2S | Z = 2 |
Mr = 290.37 | F(000) = 308 |
Triclinic, P1 | Dx = 1.387 Mg m−3 |
a = 7.4536 (1) Å | Mo Kα radiation, λ = 0.7107 Å |
b = 7.4603 (2) Å | Cell parameters from 11838 reflections |
c = 13.6011 (3) Å | θ = 1–27.5° |
α = 79.6877 (12)° | µ = 0.24 mm−1 |
β = 89.2981 (14)° | T = 150 K |
γ = 69.3688 (12)° | Plate, colourless |
V = 695.31 (3) Å3 | 0.45 × 0.32 × 0.2 mm |
Data collection top
Nonius KappaCCD area detector diffractometer | Rint = 0.031 |
Radiation source: fine-focus sealed tube | θmax = 27.4°, θmin = 3.0° |
φ and ω scans to fill the Ewald sphere | h = −9→9 |
17028 measured reflections | k = −9→9 |
6242 independent reflections | l = −17→17 |
6027 reflections with I > 2σ(I) | |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.029 | w = 1/[σ2(Fo2) + (0.0468P)2 + 0.0971P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.079 | (Δ/σ)max < 0.001 |
S = 1.04 | Δρmax = 0.22 e Å−3 |
6242 reflections | Δρmin = −0.20 e Å−3 |
363 parameters | Absolute structure: Flack x determined using 2865 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
3 restraints | Absolute structure parameter: 0.022 (19) |
Secondary atom site location: difference Fourier map | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.1876 (3) | 0.2874 (3) | 0.04004 (13) | 0.0175 (4) | |
C2 | 0.2259 (3) | 0.1522 (3) | −0.01870 (15) | 0.0182 (4) | |
O2 | 0.1243 (2) | 0.0558 (3) | −0.02513 (13) | 0.0280 (4) | |
C3 | 0.3987 (3) | 0.1223 (3) | −0.08201 (16) | 0.0171 (4) | |
H3 | 0.3518 | 0.1368 | −0.1510 | 0.020* | |
N4 | 0.4902 (3) | 0.2669 (3) | −0.08300 (14) | 0.0178 (4) | |
C4 | 0.6324 (3) | 0.2706 (4) | −0.15787 (18) | 0.0243 (5) | |
H4A | 0.6340 | 0.4004 | −0.1758 | 0.037* | |
H4B | 0.5992 | 0.2307 | −0.2163 | 0.037* | |
H4C | 0.7571 | 0.1830 | −0.1306 | 0.037* | |
C5 | 0.4782 (3) | 0.3689 (3) | −0.00977 (17) | 0.0190 (4) | |
O5 | 0.5825 (3) | 0.4630 (2) | −0.00267 (14) | 0.0290 (4) | |
C6 | 0.3232 (3) | 0.3770 (3) | 0.06461 (16) | 0.0182 (4) | |
H6 | 0.2482 | 0.5154 | 0.0621 | 0.022* | |
C7 | 0.4106 (3) | 0.2946 (3) | 0.17251 (17) | 0.0217 (4) | |
H7A | 0.4860 | 0.1571 | 0.1785 | 0.026* | |
H7B | 0.4961 | 0.3604 | 0.1866 | 0.026* | |
C8 | 0.2572 (4) | 0.3202 (4) | 0.24932 (19) | 0.0263 (5) | |
H8A | 0.1859 | 0.4582 | 0.2455 | 0.032* | |
H8B | 0.3190 | 0.2681 | 0.3159 | 0.032* | |
S9 | 0.09101 (7) | 0.19901 (8) | 0.23000 (4) | 0.02701 (15) | |
C10 | 0.0216 (3) | 0.3201 (4) | 0.10145 (17) | 0.0228 (5) | |
H10A | −0.0686 | 0.2716 | 0.0747 | 0.027* | |
H10B | −0.0421 | 0.4589 | 0.0990 | 0.027* | |
C11 | 0.5430 (3) | −0.0889 (3) | −0.05250 (17) | 0.0205 (4) | |
H11A | 0.4770 | −0.1781 | −0.0581 | 0.025* | |
H11B | 0.6435 | −0.1095 | −0.0997 | 0.025* | |
C12 | 0.6340 (3) | −0.1376 (3) | 0.05179 (17) | 0.0195 (4) | |
C13 | 0.5541 (3) | −0.2198 (3) | 0.13250 (18) | 0.0222 (5) | |
H13 | 0.4424 | −0.2442 | 0.1220 | 0.027* | |
C14 | 0.6392 (4) | −0.2661 (4) | 0.22882 (19) | 0.0276 (5) | |
H14 | 0.5850 | −0.3223 | 0.2819 | 0.033* | |
C15 | 0.8044 (4) | −0.2287 (3) | 0.24563 (19) | 0.0284 (5) | |
H15 | 0.8612 | −0.2589 | 0.3099 | 0.034* | |
C16 | 0.8843 (4) | −0.1455 (4) | 0.1655 (2) | 0.0282 (5) | |
H16 | 0.9949 | −0.1195 | 0.1764 | 0.034* | |
C17 | 0.8008 (3) | −0.1011 (3) | 0.06986 (19) | 0.0240 (5) | |
H17 | 0.8564 | −0.0462 | 0.0169 | 0.029* | |
N21 | −0.1328 (3) | 0.1550 (3) | −0.35899 (13) | 0.0182 (4) | |
C22 | 0.0295 (3) | 0.0907 (3) | −0.30047 (16) | 0.0184 (4) | |
O22 | 0.1282 (3) | 0.1905 (2) | −0.29408 (13) | 0.0279 (4) | |
C23 | 0.0905 (3) | −0.1113 (3) | −0.23659 (16) | 0.0172 (4) | |
H23 | 0.1088 | −0.0962 | −0.1677 | 0.021* | |
N24 | −0.0528 (3) | −0.2046 (3) | −0.23505 (14) | 0.0179 (4) | |
C24 | −0.0188 (3) | −0.3823 (3) | −0.16022 (18) | 0.0241 (5) | |
H24A | −0.1396 | −0.3939 | −0.1418 | 0.036* | |
H24B | 0.0488 | −0.3760 | −0.1021 | 0.036* | |
H24C | 0.0565 | −0.4935 | −0.1877 | 0.036* | |
C25 | −0.1903 (3) | −0.1596 (3) | −0.30785 (17) | 0.0196 (4) | |
O25 | −0.2873 (2) | −0.2605 (3) | −0.31402 (14) | 0.0292 (4) | |
C26 | −0.2338 (3) | 0.0303 (3) | −0.38275 (16) | 0.0186 (4) | |
H26 | −0.3711 | 0.1038 | −0.3803 | 0.022* | |
C27 | −0.2020 (3) | −0.0090 (3) | −0.49018 (16) | 0.0211 (4) | |
H27A | −0.0671 | −0.0819 | −0.4959 | 0.025* | |
H27B | −0.2744 | −0.0884 | −0.5035 | 0.025* | |
C28 | −0.2637 (4) | 0.1794 (4) | −0.56857 (18) | 0.0259 (5) | |
H28A | −0.4002 | 0.2487 | −0.5654 | 0.031* | |
H28B | −0.2416 | 0.1469 | −0.6347 | 0.031* | |
S29 | −0.13449 (8) | 0.33726 (8) | −0.55012 (4) | 0.02691 (14) | |
C210 | −0.1954 (3) | 0.3488 (3) | −0.42137 (17) | 0.0235 (5) | |
H21A | −0.1350 | 0.4277 | −0.3953 | 0.028* | |
H21B | −0.3333 | 0.4107 | −0.4189 | 0.028* | |
C211 | 0.2882 (3) | −0.2410 (3) | −0.26655 (17) | 0.0218 (4) | |
H21C | 0.3807 | −0.1789 | −0.2597 | 0.026* | |
H21D | 0.3304 | −0.3651 | −0.2204 | 0.026* | |
C212 | 0.2875 (3) | −0.2782 (3) | −0.37139 (17) | 0.0192 (4) | |
C213 | 0.2435 (3) | −0.4345 (3) | −0.39265 (19) | 0.0251 (5) | |
H213 | 0.2166 | −0.5193 | −0.3408 | 0.030* | |
C214 | 0.2394 (4) | −0.4652 (4) | −0.4906 (2) | 0.0315 (6) | |
H214 | 0.2085 | −0.5692 | −0.5038 | 0.038* | |
C215 | 0.2811 (4) | −0.3415 (4) | −0.56785 (19) | 0.0312 (6) | |
H215 | 0.2794 | −0.3627 | −0.6331 | 0.037* | |
C216 | 0.3258 (4) | −0.1852 (4) | −0.54826 (19) | 0.0276 (5) | |
H216 | 0.3539 | −0.1015 | −0.6003 | 0.033* | |
C217 | 0.3283 (3) | −0.1546 (3) | −0.45085 (18) | 0.0221 (5) | |
H217 | 0.3577 | −0.0493 | −0.4382 | 0.027* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0174 (9) | 0.0208 (9) | 0.0150 (9) | −0.0072 (7) | 0.0008 (7) | −0.0048 (7) |
C2 | 0.0182 (10) | 0.0206 (10) | 0.0157 (10) | −0.0067 (8) | 0.0000 (8) | −0.0033 (8) |
O2 | 0.0271 (9) | 0.0370 (9) | 0.0298 (9) | −0.0196 (8) | 0.0068 (7) | −0.0150 (8) |
C3 | 0.0198 (11) | 0.0187 (10) | 0.0158 (10) | −0.0093 (8) | 0.0014 (8) | −0.0057 (8) |
N4 | 0.0179 (9) | 0.0179 (8) | 0.0179 (9) | −0.0076 (7) | 0.0036 (7) | −0.0015 (7) |
C4 | 0.0226 (11) | 0.0240 (11) | 0.0234 (12) | −0.0067 (9) | 0.0073 (9) | −0.0007 (9) |
C5 | 0.0177 (10) | 0.0145 (9) | 0.0225 (11) | −0.0037 (8) | −0.0010 (8) | −0.0018 (8) |
O5 | 0.0310 (9) | 0.0252 (9) | 0.0382 (10) | −0.0175 (7) | 0.0042 (7) | −0.0089 (7) |
C6 | 0.0194 (10) | 0.0153 (9) | 0.0197 (10) | −0.0052 (8) | −0.0011 (8) | −0.0052 (8) |
C7 | 0.0241 (11) | 0.0199 (10) | 0.0208 (11) | −0.0068 (9) | −0.0040 (9) | −0.0053 (8) |
C8 | 0.0322 (13) | 0.0273 (12) | 0.0193 (11) | −0.0086 (10) | −0.0014 (9) | −0.0081 (9) |
S9 | 0.0292 (3) | 0.0359 (3) | 0.0174 (3) | −0.0132 (3) | 0.0048 (2) | −0.0058 (2) |
C10 | 0.0182 (10) | 0.0284 (12) | 0.0210 (11) | −0.0057 (9) | 0.0030 (8) | −0.0079 (9) |
C11 | 0.0252 (11) | 0.0169 (10) | 0.0208 (11) | −0.0076 (9) | 0.0042 (9) | −0.0067 (8) |
C12 | 0.0202 (11) | 0.0121 (9) | 0.0246 (11) | −0.0031 (8) | 0.0032 (9) | −0.0050 (8) |
C13 | 0.0214 (11) | 0.0189 (11) | 0.0268 (12) | −0.0074 (9) | 0.0031 (9) | −0.0051 (9) |
C14 | 0.0316 (14) | 0.0224 (12) | 0.0236 (12) | −0.0052 (10) | 0.0049 (10) | −0.0005 (9) |
C15 | 0.0328 (13) | 0.0216 (11) | 0.0238 (12) | −0.0022 (10) | −0.0075 (10) | −0.0014 (9) |
C16 | 0.0230 (11) | 0.0225 (11) | 0.0381 (14) | −0.0078 (9) | −0.0051 (10) | −0.0035 (10) |
C17 | 0.0216 (11) | 0.0183 (11) | 0.0305 (13) | −0.0075 (9) | 0.0020 (9) | 0.0001 (9) |
N21 | 0.0202 (9) | 0.0165 (8) | 0.0165 (9) | −0.0055 (7) | −0.0004 (7) | −0.0016 (7) |
C22 | 0.0215 (10) | 0.0181 (10) | 0.0159 (10) | −0.0072 (8) | 0.0018 (8) | −0.0041 (8) |
O22 | 0.0336 (9) | 0.0248 (8) | 0.0297 (9) | −0.0173 (7) | −0.0056 (7) | −0.0013 (7) |
C23 | 0.0176 (10) | 0.0195 (10) | 0.0142 (10) | −0.0071 (8) | −0.0017 (7) | −0.0014 (8) |
N24 | 0.0186 (9) | 0.0168 (8) | 0.0176 (9) | −0.0070 (7) | 0.0010 (7) | 0.0005 (7) |
C24 | 0.0253 (11) | 0.0195 (10) | 0.0232 (11) | −0.0059 (9) | 0.0028 (9) | 0.0026 (9) |
C25 | 0.0150 (10) | 0.0216 (10) | 0.0218 (11) | −0.0054 (8) | 0.0037 (8) | −0.0060 (9) |
O25 | 0.0230 (8) | 0.0317 (9) | 0.0371 (10) | −0.0162 (7) | 0.0000 (7) | −0.0036 (8) |
C26 | 0.0135 (10) | 0.0225 (11) | 0.0190 (10) | −0.0052 (8) | −0.0004 (8) | −0.0039 (8) |
C27 | 0.0184 (10) | 0.0263 (11) | 0.0192 (11) | −0.0074 (9) | 0.0000 (8) | −0.0069 (9) |
C28 | 0.0243 (12) | 0.0345 (13) | 0.0162 (11) | −0.0078 (10) | −0.0013 (9) | −0.0034 (9) |
S29 | 0.0321 (3) | 0.0273 (3) | 0.0182 (3) | −0.0099 (2) | −0.0001 (2) | 0.0021 (2) |
C210 | 0.0276 (12) | 0.0177 (10) | 0.0213 (11) | −0.0045 (9) | 0.0008 (9) | −0.0012 (9) |
C211 | 0.0167 (10) | 0.0238 (11) | 0.0219 (11) | −0.0053 (9) | −0.0025 (8) | −0.0003 (9) |
C212 | 0.0119 (10) | 0.0214 (10) | 0.0215 (11) | −0.0027 (8) | 0.0006 (8) | −0.0038 (9) |
C213 | 0.0197 (11) | 0.0207 (11) | 0.0344 (13) | −0.0058 (9) | 0.0066 (9) | −0.0070 (10) |
C214 | 0.0231 (12) | 0.0312 (13) | 0.0453 (15) | −0.0097 (10) | 0.0061 (11) | −0.0206 (12) |
C215 | 0.0240 (12) | 0.0431 (15) | 0.0291 (13) | −0.0098 (11) | 0.0039 (10) | −0.0182 (11) |
C216 | 0.0237 (13) | 0.0344 (14) | 0.0240 (12) | −0.0095 (10) | 0.0038 (10) | −0.0051 (11) |
C217 | 0.0183 (11) | 0.0230 (11) | 0.0258 (11) | −0.0080 (9) | 0.0008 (8) | −0.0049 (9) |
Geometric parameters (Å, º) top
N1—C2 | 1.348 (3) | N21—C22 | 1.343 (3) |
N1—C10 | 1.457 (3) | N21—C210 | 1.457 (3) |
N1—C6 | 1.464 (3) | N21—C26 | 1.464 (3) |
C2—O2 | 1.228 (3) | C22—O22 | 1.231 (3) |
C2—C3 | 1.513 (3) | C22—C23 | 1.514 (3) |
C3—N4 | 1.463 (3) | C23—N24 | 1.464 (3) |
C3—C11 | 1.546 (3) | C23—C211 | 1.548 (3) |
C3—H3 | 0.9800 | C23—H23 | 0.9800 |
N4—C5 | 1.342 (3) | N24—C25 | 1.344 (3) |
N4—C4 | 1.464 (3) | N24—C24 | 1.464 (3) |
C4—H4A | 0.9600 | C24—H24A | 0.9600 |
C4—H4B | 0.9600 | C24—H24B | 0.9600 |
C4—H4C | 0.9600 | C24—H24C | 0.9600 |
C5—O5 | 1.232 (3) | C25—O25 | 1.227 (3) |
C5—C6 | 1.519 (3) | C25—C26 | 1.522 (3) |
C6—C7 | 1.541 (3) | C26—C27 | 1.540 (3) |
C6—H6 | 0.9800 | C26—H26 | 0.9800 |
C7—C8 | 1.524 (3) | C27—C28 | 1.531 (3) |
C7—H7A | 0.9700 | C27—H27A | 0.9700 |
C7—H7B | 0.9700 | C27—H27B | 0.9700 |
C8—S9 | 1.817 (3) | C28—S29 | 1.814 (3) |
C8—H8A | 0.9700 | C28—H28A | 0.9700 |
C8—H8B | 0.9700 | C28—H28B | 0.9700 |
S9—C10 | 1.808 (2) | S29—C210 | 1.813 (2) |
C10—H10A | 0.9700 | C210—H21A | 0.9700 |
C10—H10B | 0.9700 | C210—H21B | 0.9700 |
C11—C12 | 1.507 (3) | C211—C212 | 1.501 (3) |
C11—H11A | 0.9700 | C211—H21C | 0.9700 |
C11—H11B | 0.9700 | C211—H21D | 0.9700 |
C12—C13 | 1.392 (3) | C212—C213 | 1.393 (3) |
C12—C17 | 1.397 (3) | C212—C217 | 1.395 (3) |
C13—C14 | 1.394 (4) | C213—C214 | 1.394 (4) |
C13—H13 | 0.9300 | C213—H213 | 0.9300 |
C14—C15 | 1.385 (4) | C214—C215 | 1.378 (4) |
C14—H14 | 0.9300 | C214—H214 | 0.9300 |
C15—C16 | 1.389 (4) | C215—C216 | 1.388 (4) |
C15—H15 | 0.9300 | C215—H215 | 0.9300 |
C16—C17 | 1.382 (4) | C216—C217 | 1.386 (4) |
C16—H16 | 0.9300 | C216—H216 | 0.9300 |
C17—H17 | 0.9300 | C217—H217 | 0.9300 |
| | | |
C2—N1—C10 | 119.68 (18) | C22—N21—C210 | 119.92 (18) |
C2—N1—C6 | 124.19 (18) | C22—N21—C26 | 124.30 (17) |
C10—N1—C6 | 114.75 (18) | C210—N21—C26 | 114.44 (18) |
O2—C2—N1 | 123.0 (2) | O22—C22—N21 | 123.10 (19) |
O2—C2—C3 | 118.52 (19) | O22—C22—C23 | 118.28 (19) |
N1—C2—C3 | 118.44 (18) | N21—C22—C23 | 118.58 (18) |
N4—C3—C2 | 114.36 (17) | N24—C23—C22 | 114.30 (17) |
N4—C3—C11 | 112.27 (17) | N24—C23—C211 | 112.13 (18) |
C2—C3—C11 | 110.31 (17) | C22—C23—C211 | 110.22 (18) |
N4—C3—H3 | 106.4 | N24—C23—H23 | 106.6 |
C2—C3—H3 | 106.4 | C22—C23—H23 | 106.6 |
C11—C3—H3 | 106.4 | C211—C23—H23 | 106.6 |
C5—N4—C3 | 123.86 (18) | C25—N24—C24 | 117.99 (18) |
C5—N4—C4 | 118.07 (19) | C25—N24—C23 | 124.06 (18) |
C3—N4—C4 | 116.92 (18) | C24—N24—C23 | 116.76 (17) |
N4—C4—H4A | 109.5 | N24—C24—H24A | 109.5 |
N4—C4—H4B | 109.5 | N24—C24—H24B | 109.5 |
H4A—C4—H4B | 109.5 | H24A—C24—H24B | 109.5 |
N4—C4—H4C | 109.5 | N24—C24—H24C | 109.5 |
H4A—C4—H4C | 109.5 | H24A—C24—H24C | 109.5 |
H4B—C4—H4C | 109.5 | H24B—C24—H24C | 109.5 |
O5—C5—N4 | 122.8 (2) | O25—C25—N24 | 122.9 (2) |
O5—C5—C6 | 118.5 (2) | O25—C25—C26 | 118.7 (2) |
N4—C5—C6 | 118.68 (19) | N24—C25—C26 | 118.34 (19) |
N1—C6—C5 | 114.10 (18) | N21—C26—C25 | 114.26 (18) |
N1—C6—C7 | 111.66 (18) | N21—C26—C27 | 111.84 (17) |
C5—C6—C7 | 111.32 (18) | C25—C26—C27 | 110.85 (18) |
N1—C6—H6 | 106.4 | N21—C26—H26 | 106.4 |
C5—C6—H6 | 106.4 | C25—C26—H26 | 106.4 |
C7—C6—H6 | 106.4 | C27—C26—H26 | 106.4 |
C8—C7—C6 | 112.16 (19) | C28—C27—C26 | 112.33 (19) |
C8—C7—H7A | 109.2 | C28—C27—H27A | 109.1 |
C6—C7—H7A | 109.2 | C26—C27—H27A | 109.1 |
C8—C7—H7B | 109.2 | C28—C27—H27B | 109.1 |
C6—C7—H7B | 109.2 | C26—C27—H27B | 109.1 |
H7A—C7—H7B | 107.9 | H27A—C27—H27B | 107.9 |
C7—C8—S9 | 112.48 (16) | C27—C28—S29 | 112.34 (16) |
C7—C8—H8A | 109.1 | C27—C28—H28A | 109.1 |
S9—C8—H8A | 109.1 | S29—C28—H28A | 109.1 |
C7—C8—H8B | 109.1 | C27—C28—H28B | 109.1 |
S9—C8—H8B | 109.1 | S29—C28—H28B | 109.1 |
H8A—C8—H8B | 107.8 | H28A—C28—H28B | 107.9 |
C10—S9—C8 | 95.64 (11) | C210—S29—C28 | 95.87 (11) |
N1—C10—S9 | 111.34 (15) | N21—C210—S29 | 111.30 (15) |
N1—C10—H10A | 109.4 | N21—C210—H21A | 109.4 |
S9—C10—H10A | 109.4 | S29—C210—H21A | 109.4 |
N1—C10—H10B | 109.4 | N21—C210—H21B | 109.4 |
S9—C10—H10B | 109.4 | S29—C210—H21B | 109.4 |
H10A—C10—H10B | 108.0 | H21A—C210—H21B | 108.0 |
C12—C11—C3 | 114.16 (17) | C212—C211—C23 | 113.88 (17) |
C12—C11—H11A | 108.7 | C212—C211—H21C | 108.8 |
C3—C11—H11A | 108.7 | C23—C211—H21C | 108.8 |
C12—C11—H11B | 108.7 | C212—C211—H21D | 108.8 |
C3—C11—H11B | 108.7 | C23—C211—H21D | 108.8 |
H11A—C11—H11B | 107.6 | H21C—C211—H21D | 107.7 |
C13—C12—C17 | 118.3 (2) | C213—C212—C217 | 118.0 (2) |
C13—C12—C11 | 120.9 (2) | C213—C212—C211 | 121.4 (2) |
C17—C12—C11 | 120.8 (2) | C217—C212—C211 | 120.6 (2) |
C12—C13—C14 | 120.8 (2) | C212—C213—C214 | 120.9 (2) |
C12—C13—H13 | 119.6 | C212—C213—H213 | 119.6 |
C14—C13—H13 | 119.6 | C214—C213—H213 | 119.6 |
C15—C14—C13 | 120.2 (2) | C215—C214—C213 | 120.0 (2) |
C15—C14—H14 | 119.9 | C215—C214—H214 | 120.0 |
C13—C14—H14 | 119.9 | C213—C214—H214 | 120.0 |
C14—C15—C16 | 119.3 (2) | C214—C215—C216 | 120.0 (2) |
C14—C15—H15 | 120.3 | C214—C215—H215 | 120.0 |
C16—C15—H15 | 120.3 | C216—C215—H215 | 120.0 |
C17—C16—C15 | 120.5 (2) | C217—C216—C215 | 119.7 (2) |
C17—C16—H16 | 119.7 | C217—C216—H216 | 120.1 |
C15—C16—H16 | 119.7 | C215—C216—H216 | 120.1 |
C16—C17—C12 | 120.8 (2) | C216—C217—C212 | 121.3 (2) |
C16—C17—H17 | 119.6 | C216—C217—H217 | 119.3 |
C12—C17—H17 | 119.6 | C212—C217—H217 | 119.3 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O22 | 0.98 | 2.46 | 3.397 (3) | 160 |
C11—H11A···O5i | 0.97 | 2.48 | 3.197 (3) | 130 |
C17—H17···O2ii | 0.93 | 2.40 | 3.197 (3) | 143 |
C211—H21C···O25ii | 0.97 | 2.47 | 3.179 (3) | 130 |
C23—H23···O2 | 0.98 | 2.44 | 3.378 (3) | 161 |
C213—H213···O22i | 0.93 | 2.45 | 3.269 (3) | 146 |
Symmetry codes: (i) x, y−1, z; (ii) x+1, y, z. |
Crystal data top
C15H18N2O2S | F(000) = 616 |
Mr = 290.37 | Dx = 1.341 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71070 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 14664 reflections |
a = 9.8689 (2) Å | θ = 1–27.5° |
b = 10.6838 (2) Å | µ = 0.23 mm−1 |
c = 13.6421 (2) Å | T = 150 K |
V = 1438.39 (4) Å3 | Prism, colourles |
Z = 4 | 0.4 × 0.25 × 0.25 mm |
Data collection top
Nonius KappaCCD area detector diffractometer | 3045 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.035 |
Graphite monochromator | θmax = 27.5°, θmin = 2.8° |
Detector resolution: 9.091 pixels mm-1 | h = 0→12 |
φ and ω scans to fill the Ewald sphere | k = 0→13 |
25952 measured reflections | l = −17→17 |
3291 independent reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.031 | w = 1/[σ2(Fo2) + (0.0369P)2 + 0.3211P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.077 | (Δ/σ)max < 0.001 |
S = 1.06 | Δρmax = 0.20 e Å−3 |
3291 reflections | Δρmin = −0.18 e Å−3 |
183 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.044 (2) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.01 (7) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F2, conventional R-factors R are based
on F, with F set to zero for negative F2. The threshold expression of
F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F2 are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.28236 (13) | 0.78426 (11) | 0.10568 (8) | 0.0256 (3) | |
C2 | 0.21533 (15) | 0.88543 (13) | 0.13948 (11) | 0.0260 (3) | |
C3 | 0.13535 (14) | 0.87245 (12) | 0.23322 (10) | 0.0247 (3) | |
H3 | 0.0510 | 0.9198 | 0.2252 | 0.030* | |
N4 | 0.09891 (11) | 0.74383 (11) | 0.25736 (9) | 0.0230 (3) | |
C4 | −0.00986 (16) | 0.72775 (15) | 0.32923 (11) | 0.0325 (3) | |
H4A | −0.0588 | 0.6522 | 0.3151 | 0.049* | |
H4B | −0.0705 | 0.7979 | 0.3259 | 0.049* | |
H4C | 0.0284 | 0.7226 | 0.3938 | 0.049* | |
C5 | 0.16656 (13) | 0.64327 (13) | 0.22624 (10) | 0.0215 (3) | |
C6 | 0.27321 (14) | 0.65846 (13) | 0.14681 (10) | 0.0225 (3) | |
H6 | 0.3614 | 0.6379 | 0.1756 | 0.027* | |
C7 | 0.24381 (16) | 0.56212 (14) | 0.06594 (11) | 0.0295 (3) | |
H7A | 0.2403 | 0.4794 | 0.0951 | 0.035* | |
H7B | 0.1554 | 0.5796 | 0.0381 | 0.035* | |
C8 | 0.3480 (2) | 0.56163 (17) | −0.01575 (12) | 0.0403 (4) | |
H8A | 0.3257 | 0.4964 | −0.0625 | 0.048* | |
H8B | 0.4366 | 0.5431 | 0.0114 | 0.048* | |
S9 | 0.35366 (5) | 0.71083 (4) | −0.07809 (3) | 0.04405 (14) | |
C10 | 0.38512 (16) | 0.80154 (17) | 0.03036 (11) | 0.0352 (4) | |
H10A | 0.4728 | 0.7784 | 0.0570 | 0.042* | |
H10B | 0.3889 | 0.8894 | 0.0127 | 0.042* | |
C11 | 0.21673 (16) | 0.93424 (15) | 0.31800 (12) | 0.0300 (3) | |
H11A | 0.2338 | 1.0213 | 0.3021 | 0.036* | |
H11B | 0.1631 | 0.9318 | 0.3776 | 0.036* | |
C12 | 0.34986 (16) | 0.86860 (13) | 0.33545 (10) | 0.0267 (3) | |
C13 | 0.46417 (15) | 0.90170 (15) | 0.28157 (12) | 0.0319 (3) | |
H13 | 0.4605 | 0.9702 | 0.2396 | 0.038* | |
C14 | 0.58348 (16) | 0.83375 (16) | 0.28969 (14) | 0.0377 (4) | |
H14 | 0.6592 | 0.8571 | 0.2535 | 0.045* | |
C15 | 0.58988 (17) | 0.73134 (16) | 0.35165 (13) | 0.0383 (4) | |
H15 | 0.6693 | 0.6850 | 0.3565 | 0.046* | |
C16 | 0.47739 (18) | 0.69845 (16) | 0.40622 (12) | 0.0377 (4) | |
H16 | 0.4814 | 0.6300 | 0.4483 | 0.045* | |
C17 | 0.35842 (17) | 0.76714 (15) | 0.39854 (11) | 0.0322 (3) | |
H17 | 0.2836 | 0.7448 | 0.4361 | 0.039* | |
O2 | 0.22419 (12) | 0.98925 (10) | 0.10066 (9) | 0.0373 (3) | |
O5 | 0.14323 (11) | 0.53662 (9) | 0.25671 (8) | 0.0301 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0293 (6) | 0.0238 (6) | 0.0236 (6) | −0.0026 (5) | 0.0033 (5) | 0.0010 (5) |
C2 | 0.0270 (7) | 0.0232 (7) | 0.0278 (7) | −0.0025 (6) | −0.0062 (6) | 0.0008 (6) |
C3 | 0.0235 (6) | 0.0196 (6) | 0.0311 (7) | 0.0022 (6) | −0.0011 (6) | −0.0018 (5) |
N4 | 0.0210 (5) | 0.0230 (6) | 0.0250 (6) | −0.0004 (4) | 0.0015 (5) | −0.0008 (5) |
C4 | 0.0292 (7) | 0.0359 (8) | 0.0325 (8) | −0.0002 (7) | 0.0092 (6) | −0.0026 (7) |
C5 | 0.0203 (6) | 0.0231 (7) | 0.0211 (6) | −0.0009 (5) | −0.0020 (5) | 0.0012 (5) |
C6 | 0.0221 (6) | 0.0241 (7) | 0.0214 (6) | 0.0012 (5) | −0.0001 (5) | 0.0000 (5) |
C7 | 0.0369 (8) | 0.0261 (7) | 0.0256 (7) | 0.0009 (6) | 0.0010 (6) | −0.0027 (6) |
C8 | 0.0528 (10) | 0.0406 (9) | 0.0275 (7) | 0.0073 (9) | 0.0095 (8) | −0.0070 (7) |
S9 | 0.0579 (3) | 0.0510 (3) | 0.02326 (19) | −0.0009 (2) | 0.01065 (19) | 0.00207 (18) |
C10 | 0.0364 (8) | 0.0381 (9) | 0.0312 (8) | −0.0074 (7) | 0.0091 (6) | 0.0032 (7) |
C11 | 0.0313 (8) | 0.0267 (7) | 0.0319 (8) | 0.0021 (6) | −0.0021 (6) | −0.0070 (6) |
C12 | 0.0301 (7) | 0.0249 (7) | 0.0251 (7) | −0.0012 (6) | −0.0053 (6) | −0.0075 (5) |
C13 | 0.0317 (8) | 0.0293 (8) | 0.0348 (8) | −0.0066 (6) | −0.0059 (7) | −0.0003 (6) |
C14 | 0.0272 (7) | 0.0418 (10) | 0.0441 (9) | −0.0059 (7) | −0.0016 (7) | −0.0068 (8) |
C15 | 0.0314 (8) | 0.0355 (9) | 0.0478 (10) | 0.0062 (7) | −0.0110 (7) | −0.0115 (7) |
C16 | 0.0454 (9) | 0.0318 (8) | 0.0360 (9) | 0.0030 (7) | −0.0128 (7) | 0.0017 (7) |
C17 | 0.0354 (8) | 0.0360 (8) | 0.0251 (7) | −0.0035 (7) | −0.0024 (6) | −0.0009 (6) |
O2 | 0.0445 (6) | 0.0241 (5) | 0.0432 (7) | −0.0029 (5) | −0.0011 (5) | 0.0079 (5) |
O5 | 0.0345 (5) | 0.0227 (5) | 0.0332 (5) | −0.0008 (4) | 0.0069 (5) | 0.0038 (4) |
Geometric parameters (Å, º) top
N1—C2 | 1.3486 (19) | C8—S9 | 1.8076 (18) |
N1—C10 | 1.4554 (18) | C8—H8A | 0.9700 |
N1—C6 | 1.4593 (18) | C8—H8B | 0.9700 |
C2—O2 | 1.2322 (18) | S9—C10 | 1.7956 (18) |
C2—C3 | 1.509 (2) | C10—H10A | 0.9700 |
C3—N4 | 1.4581 (18) | C10—H10B | 0.9700 |
C3—C11 | 1.555 (2) | C11—C12 | 1.508 (2) |
C3—H3 | 0.9800 | C11—H11A | 0.9700 |
N4—C5 | 1.3342 (18) | C11—H11B | 0.9700 |
N4—C4 | 1.4638 (18) | C12—C17 | 1.387 (2) |
C4—H4A | 0.9600 | C12—C13 | 1.392 (2) |
C4—H4B | 0.9600 | C13—C14 | 1.388 (2) |
C4—H4C | 0.9600 | C13—H13 | 0.9300 |
C5—O5 | 1.2346 (17) | C14—C15 | 1.384 (3) |
C5—C6 | 1.5193 (19) | C14—H14 | 0.9300 |
C6—C7 | 1.5365 (19) | C15—C16 | 1.382 (3) |
C6—H6 | 0.9800 | C15—H15 | 0.9300 |
C7—C8 | 1.516 (2) | C16—C17 | 1.388 (2) |
C7—H7A | 0.9700 | C16—H16 | 0.9300 |
C7—H7B | 0.9700 | C17—H17 | 0.9300 |
| | | |
C2—N1—C10 | 118.79 (13) | C7—C8—H8A | 109.4 |
C2—N1—C6 | 125.19 (12) | S9—C8—H8A | 109.4 |
C10—N1—C6 | 115.56 (12) | C7—C8—H8B | 109.4 |
O2—C2—N1 | 122.66 (14) | S9—C8—H8B | 109.4 |
O2—C2—C3 | 118.95 (13) | H8A—C8—H8B | 108.0 |
N1—C2—C3 | 118.21 (12) | C10—S9—C8 | 95.38 (8) |
N4—C3—C2 | 114.02 (11) | N1—C10—S9 | 113.12 (11) |
N4—C3—C11 | 111.06 (12) | N1—C10—H10A | 109.0 |
C2—C3—C11 | 108.72 (12) | S9—C10—H10A | 109.0 |
N4—C3—H3 | 107.6 | N1—C10—H10B | 109.0 |
C2—C3—H3 | 107.6 | S9—C10—H10B | 109.0 |
C11—C3—H3 | 107.6 | H10A—C10—H10B | 107.8 |
C5—N4—C3 | 124.30 (11) | C12—C11—C3 | 111.71 (12) |
C5—N4—C4 | 119.05 (12) | C12—C11—H11A | 109.3 |
C3—N4—C4 | 116.28 (11) | C3—C11—H11A | 109.3 |
N4—C4—H4A | 109.5 | C12—C11—H11B | 109.3 |
N4—C4—H4B | 109.5 | C3—C11—H11B | 109.3 |
H4A—C4—H4B | 109.5 | H11A—C11—H11B | 107.9 |
N4—C4—H4C | 109.5 | C17—C12—C13 | 118.48 (14) |
H4A—C4—H4C | 109.5 | C17—C12—C11 | 120.97 (14) |
H4B—C4—H4C | 109.5 | C13—C12—C11 | 120.29 (13) |
O5—C5—N4 | 122.86 (12) | C14—C13—C12 | 120.83 (15) |
O5—C5—C6 | 117.90 (12) | C14—C13—H13 | 119.6 |
N4—C5—C6 | 119.19 (12) | C12—C13—H13 | 119.6 |
N1—C6—C5 | 114.55 (11) | C15—C14—C13 | 120.07 (16) |
N1—C6—C7 | 110.64 (11) | C15—C14—H14 | 120.0 |
C5—C6—C7 | 108.04 (11) | C13—C14—H14 | 120.0 |
N1—C6—H6 | 107.8 | C16—C15—C14 | 119.56 (15) |
C5—C6—H6 | 107.8 | C16—C15—H15 | 120.2 |
C7—C6—H6 | 107.8 | C14—C15—H15 | 120.2 |
C8—C7—C6 | 113.71 (13) | C15—C16—C17 | 120.28 (15) |
C8—C7—H7A | 108.8 | C15—C16—H16 | 119.9 |
C6—C7—H7A | 108.8 | C17—C16—H16 | 119.9 |
C8—C7—H7B | 108.8 | C12—C17—C16 | 120.76 (15) |
C6—C7—H7B | 108.8 | C12—C17—H17 | 119.6 |
H7A—C7—H7B | 107.7 | C16—C17—H17 | 119.6 |
C7—C8—S9 | 111.33 (11) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O5i | 0.98 | 2.30 | 3.2641 (17) | 167 |
C8—H8A···O5ii | 0.97 | 2.51 | 3.2779 (19) | 136 |
C15—H15···O2iii | 0.93 | 2.41 | 3.237 (2) | 148 |
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x+1/2, −y+1, z−1/2; (iii) −x+1, y−1/2, −z+1/2. |
Crystal data top
C14H16N2O2S | Dx = 1.407 Mg m−3 |
Mr = 276.35 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, P43212 | Cell parameters from 6416 reflections |
Hall symbol: P 4nw 2abw | θ = 3.2–27.5° |
a = 7.7430 (2) Å | µ = 0.25 mm−1 |
c = 43.5343 (14) Å | T = 150 K |
V = 2610.06 (13) Å3 | Bar, colourless |
Z = 8 | 0.46 × 0.18 × 0.18 mm |
F(000) = 1168 | |
Data collection top
Bruker APEX-II CCD diffractometer | 2992 independent reflections |
Radiation source: fine-focus sealed tube | 2800 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
φ and ω scans | θmax = 27.5°, θmin = 1.9° |
Absorption correction: multi-scan SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction | h = −7→10 |
Tmin = 0.894, Tmax = 0.957 | k = −8→10 |
15598 measured reflections | l = −52→56 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.030 | H-atom parameters constrained |
wR(F2) = 0.075 | w = 1/[σ2(Fo2) + (0.0398P)2 + 0.4448P] where P = (Fo2 + 2Fc2)/3 |
S = 1.11 | (Δ/σ)max = 0.001 |
2992 reflections | Δρmax = 0.21 e Å−3 |
173 parameters | Δρmin = −0.21 e Å−3 |
0 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.06 (7) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F2, conventional R-factors R are based
on F, with F set to zero for negative F2. The threshold expression of
F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F2 are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.38721 (17) | 0.01940 (16) | 0.73082 (3) | 0.0197 (3) | |
C2 | 0.4236 (2) | −0.14453 (19) | 0.72231 (3) | 0.0182 (3) | |
C3 | 0.28391 (19) | −0.24774 (18) | 0.70624 (3) | 0.0174 (3) | |
H3 | 0.2694 | −0.3576 | 0.7180 | 0.021* | |
N4 | 0.11398 (16) | −0.16492 (16) | 0.70493 (3) | 0.0180 (3) | |
C5 | 0.0860 (2) | 0.0049 (2) | 0.70881 (3) | 0.0204 (3) | |
C6 | 0.2319 (2) | 0.11047 (18) | 0.72197 (3) | 0.0197 (3) | |
H6 | 0.1869 | 0.1711 | 0.7406 | 0.024* | |
S7 | 0.30515 (6) | 0.27642 (5) | 0.694748 (9) | 0.02662 (11) | |
C8 | 0.5216 (2) | 0.2738 (3) | 0.71089 (4) | 0.0377 (5) | |
H8A | 0.6063 | 0.2395 | 0.6950 | 0.045* | |
H8B | 0.5528 | 0.3902 | 0.7185 | 0.045* | |
C9 | 0.5242 (2) | 0.1450 (2) | 0.73721 (4) | 0.0280 (4) | |
H9A | 0.6378 | 0.0866 | 0.7383 | 0.034* | |
H9B | 0.5024 | 0.2042 | 0.7570 | 0.034* | |
C10 | −0.0291 (2) | −0.2728 (2) | 0.69390 (4) | 0.0254 (3) | |
H10A | −0.1367 | −0.2364 | 0.7038 | 0.038* | |
H10B | −0.0059 | −0.3940 | 0.6989 | 0.038* | |
H10C | −0.0403 | −0.2600 | 0.6716 | 0.038* | |
C11 | 0.3505 (2) | −0.29767 (19) | 0.67383 (3) | 0.0197 (3) | |
H11A | 0.4602 | −0.3622 | 0.6761 | 0.024* | |
H11B | 0.2657 | −0.3764 | 0.6642 | 0.024* | |
C12 | 0.3810 (2) | −0.14716 (19) | 0.65245 (3) | 0.0193 (3) | |
C13 | 0.2488 (2) | −0.08414 (19) | 0.63401 (3) | 0.0221 (3) | |
H13 | 0.1365 | −0.1328 | 0.6356 | 0.027* | |
C14 | 0.2785 (3) | 0.0489 (2) | 0.61329 (4) | 0.0303 (4) | |
H14 | 0.1869 | 0.0902 | 0.6008 | 0.036* | |
C15 | 0.4409 (3) | 0.1214 (2) | 0.61085 (4) | 0.0346 (4) | |
H15 | 0.4613 | 0.2121 | 0.5966 | 0.042* | |
C16 | 0.5740 (3) | 0.0614 (2) | 0.62924 (4) | 0.0330 (4) | |
H16 | 0.6857 | 0.1112 | 0.6276 | 0.040* | |
C17 | 0.5444 (2) | −0.0718 (2) | 0.65010 (4) | 0.0248 (3) | |
H17 | 0.6359 | −0.1117 | 0.6628 | 0.030* | |
O2 | 0.56338 (14) | −0.21299 (15) | 0.72714 (3) | 0.0270 (3) | |
O5 | −0.05266 (15) | 0.07533 (16) | 0.70351 (3) | 0.0334 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0219 (7) | 0.0169 (6) | 0.0202 (6) | −0.0028 (5) | −0.0043 (5) | −0.0001 (5) |
C2 | 0.0226 (8) | 0.0182 (7) | 0.0138 (6) | −0.0008 (6) | 0.0007 (6) | 0.0038 (6) |
C3 | 0.0201 (7) | 0.0143 (7) | 0.0178 (6) | −0.0005 (5) | 0.0002 (6) | 0.0015 (5) |
N4 | 0.0159 (6) | 0.0198 (6) | 0.0183 (6) | −0.0018 (5) | 0.0002 (5) | −0.0011 (5) |
C5 | 0.0210 (8) | 0.0209 (8) | 0.0193 (7) | 0.0013 (6) | 0.0016 (6) | 0.0028 (6) |
C6 | 0.0248 (8) | 0.0142 (7) | 0.0201 (7) | 0.0009 (6) | −0.0008 (6) | −0.0005 (6) |
S7 | 0.0361 (2) | 0.01715 (18) | 0.02665 (19) | −0.00488 (15) | −0.00655 (17) | 0.00451 (15) |
C8 | 0.0351 (10) | 0.0368 (11) | 0.0412 (10) | −0.0176 (8) | −0.0097 (8) | 0.0117 (9) |
C9 | 0.0296 (9) | 0.0260 (9) | 0.0284 (8) | −0.0107 (7) | −0.0083 (7) | −0.0002 (7) |
C10 | 0.0214 (8) | 0.0286 (8) | 0.0262 (7) | −0.0088 (6) | 0.0001 (6) | −0.0020 (7) |
C11 | 0.0252 (7) | 0.0146 (7) | 0.0192 (7) | 0.0006 (6) | 0.0013 (6) | −0.0019 (5) |
C12 | 0.0255 (8) | 0.0146 (7) | 0.0177 (7) | 0.0002 (6) | 0.0047 (6) | −0.0043 (6) |
C13 | 0.0290 (9) | 0.0186 (7) | 0.0188 (7) | −0.0004 (6) | 0.0006 (6) | −0.0038 (6) |
C14 | 0.0498 (11) | 0.0219 (8) | 0.0192 (7) | 0.0069 (8) | −0.0002 (8) | −0.0005 (6) |
C15 | 0.0596 (13) | 0.0173 (8) | 0.0269 (8) | −0.0008 (8) | 0.0183 (9) | 0.0006 (7) |
C16 | 0.0376 (10) | 0.0218 (8) | 0.0396 (10) | −0.0082 (7) | 0.0199 (8) | −0.0075 (7) |
C17 | 0.0236 (8) | 0.0210 (8) | 0.0297 (8) | 0.0011 (6) | 0.0064 (7) | −0.0048 (6) |
O2 | 0.0228 (6) | 0.0277 (6) | 0.0306 (6) | 0.0039 (5) | −0.0069 (5) | 0.0024 (5) |
O5 | 0.0213 (6) | 0.0290 (7) | 0.0499 (8) | 0.0056 (5) | −0.0027 (6) | 0.0018 (6) |
Geometric parameters (Å, º) top
N1—C2 | 1.352 (2) | C9—H9B | 0.9900 |
N1—C6 | 1.4464 (19) | C10—H10A | 0.9800 |
N1—C9 | 1.4658 (19) | C10—H10B | 0.9800 |
C2—O2 | 1.2236 (19) | C10—H10C | 0.9800 |
C2—C3 | 1.516 (2) | C11—C12 | 1.510 (2) |
C3—N4 | 1.4648 (18) | C11—H11A | 0.9900 |
C3—C11 | 1.5515 (19) | C11—H11B | 0.9900 |
C3—H3 | 1.0000 | C12—C13 | 1.390 (2) |
N4—C5 | 1.343 (2) | C12—C17 | 1.397 (2) |
N4—C10 | 1.4684 (19) | C13—C14 | 1.389 (2) |
C5—O5 | 1.2262 (19) | C13—H13 | 0.9500 |
C5—C6 | 1.507 (2) | C14—C15 | 1.381 (3) |
C6—S7 | 1.8378 (15) | C14—H14 | 0.9500 |
C6—H6 | 1.0000 | C15—C16 | 1.385 (3) |
S7—C8 | 1.8178 (19) | C15—H15 | 0.9500 |
C8—C9 | 1.519 (2) | C16—C17 | 1.393 (2) |
C8—H8A | 0.9900 | C16—H16 | 0.9500 |
C8—H8B | 0.9900 | C17—H17 | 0.9500 |
C9—H9A | 0.9900 | | |
| | | |
C2—N1—C6 | 123.92 (13) | N1—C9—H9B | 110.4 |
C2—N1—C9 | 121.61 (14) | C8—C9—H9B | 110.4 |
C6—N1—C9 | 109.21 (12) | H9A—C9—H9B | 108.6 |
O2—C2—N1 | 122.95 (14) | N4—C10—H10A | 109.5 |
O2—C2—C3 | 118.82 (14) | N4—C10—H10B | 109.5 |
N1—C2—C3 | 118.22 (13) | H10A—C10—H10B | 109.5 |
N4—C3—C2 | 115.34 (12) | N4—C10—H10C | 109.5 |
N4—C3—C11 | 111.86 (12) | H10A—C10—H10C | 109.5 |
C2—C3—C11 | 108.29 (12) | H10B—C10—H10C | 109.5 |
N4—C3—H3 | 107.0 | C12—C11—C3 | 114.85 (12) |
C2—C3—H3 | 107.0 | C12—C11—H11A | 108.6 |
C11—C3—H3 | 107.0 | C3—C11—H11A | 108.6 |
C5—N4—C3 | 124.65 (12) | C12—C11—H11B | 108.6 |
C5—N4—C10 | 118.44 (13) | C3—C11—H11B | 108.6 |
C3—N4—C10 | 116.21 (12) | H11A—C11—H11B | 107.5 |
O5—C5—N4 | 123.57 (15) | C13—C12—C17 | 118.58 (15) |
O5—C5—C6 | 119.11 (14) | C13—C12—C11 | 120.79 (14) |
N4—C5—C6 | 117.25 (13) | C17—C12—C11 | 120.60 (14) |
N1—C6—C5 | 117.38 (12) | C14—C13—C12 | 120.93 (16) |
N1—C6—S7 | 104.82 (10) | C14—C13—H13 | 119.5 |
C5—C6—S7 | 111.43 (10) | C12—C13—H13 | 119.5 |
N1—C6—H6 | 107.6 | C15—C14—C13 | 120.14 (17) |
C5—C6—H6 | 107.6 | C15—C14—H14 | 119.9 |
S7—C6—H6 | 107.6 | C13—C14—H14 | 119.9 |
C8—S7—C6 | 91.57 (8) | C14—C15—C16 | 119.76 (16) |
C9—C8—S7 | 108.13 (12) | C14—C15—H15 | 120.1 |
C9—C8—H8A | 110.1 | C16—C15—H15 | 120.1 |
S7—C8—H8A | 110.1 | C15—C16—C17 | 120.21 (17) |
C9—C8—H8B | 110.1 | C15—C16—H16 | 119.9 |
S7—C8—H8B | 110.1 | C17—C16—H16 | 119.9 |
H8A—C8—H8B | 108.4 | C16—C17—C12 | 120.37 (16) |
N1—C9—C8 | 106.42 (13) | C16—C17—H17 | 119.8 |
N1—C9—H9A | 110.4 | C12—C17—H17 | 119.8 |
C8—C9—H9A | 110.4 | | |
| | | |
C6—N1—C2—O2 | 171.76 (14) | N4—C5—C6—N1 | −3.0 (2) |
C9—N1—C2—O2 | 20.2 (2) | O5—C5—C6—S7 | −65.32 (17) |
C6—N1—C2—C3 | −8.6 (2) | N4—C5—C6—S7 | 117.83 (13) |
C9—N1—C2—C3 | −160.19 (13) | N1—C6—S7—C8 | −24.08 (12) |
O2—C2—C3—N4 | 172.33 (13) | C5—C6—S7—C8 | −152.02 (12) |
N1—C2—C3—N4 | −7.31 (18) | C6—S7—C8—C9 | −1.01 (15) |
O2—C2—C3—C11 | −61.48 (16) | C2—N1—C9—C8 | 108.88 (17) |
N1—C2—C3—C11 | 118.88 (14) | C6—N1—C9—C8 | −46.39 (18) |
C2—C3—N4—C5 | 19.1 (2) | S7—C8—C9—N1 | 25.71 (19) |
C11—C3—N4—C5 | −105.20 (16) | N4—C3—C11—C12 | 63.34 (16) |
C2—C3—N4—C10 | −170.70 (12) | C2—C3—C11—C12 | −64.85 (16) |
C11—C3—N4—C10 | 64.96 (16) | C3—C11—C12—C13 | −88.38 (17) |
C3—N4—C5—O5 | 169.62 (15) | C3—C11—C12—C17 | 93.65 (17) |
C10—N4—C5—O5 | −0.3 (2) | C17—C12—C13—C14 | 1.0 (2) |
C3—N4—C5—C6 | −13.7 (2) | C11—C12—C13—C14 | −176.96 (13) |
C10—N4—C5—C6 | 176.37 (13) | C12—C13—C14—C15 | −0.3 (2) |
C2—N1—C6—C5 | 14.4 (2) | C13—C14—C15—C16 | −0.3 (2) |
C9—N1—C6—C5 | 168.93 (13) | C14—C15—C16—C17 | 0.1 (2) |
C2—N1—C6—S7 | −109.88 (14) | C15—C16—C17—C12 | 0.6 (2) |
C9—N1—C6—S7 | 44.70 (13) | C13—C12—C17—C16 | −1.2 (2) |
O5—C5—C6—N1 | 173.84 (14) | C11—C12—C17—C16 | 176.81 (14) |
Crystal data top
C14H16N2O2S | F(000) = 584 |
Mr = 276.35 | Dx = 1.357 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 4807 reflections |
a = 10.0987 (4) Å | θ = 2.6–27.4° |
b = 11.0883 (4) Å | µ = 0.24 mm−1 |
c = 12.0825 (5) Å | T = 150 K |
V = 1352.97 (9) Å3 | Prism, colourless |
Z = 4 | 0.54 × 0.41 × 0.26 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 3096 independent reflections |
Radiation source: fine-focus sealed tube | 2931 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
φ and ω scans | θmax = 27.5°, θmin = 2.5° |
Absorption correction: multi-scan SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction | h = −13→12 |
Tmin = 0.863, Tmax = 0.941 | k = −14→10 |
8542 measured reflections | l = −15→13 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.028 | H-atom parameters constrained |
wR(F2) = 0.069 | w = 1/[σ2(Fo2) + (0.0351P)2 + 0.2268P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.001 |
3096 reflections | Δρmax = 0.18 e Å−3 |
173 parameters | Δρmin = −0.22 e Å−3 |
0 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.01 (6) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F2, conventional R-factors R are based
on F, with F set to zero for negative F2. The threshold expression of
F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F2 are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.22369 (12) | 0.77660 (10) | 0.41260 (9) | 0.0210 (2) | |
C2 | 0.28328 (13) | 0.87153 (12) | 0.36511 (11) | 0.0197 (3) | |
C3 | 0.35435 (12) | 0.84942 (11) | 0.25659 (11) | 0.0180 (2) | |
H3 | 0.4353 | 0.9013 | 0.2574 | 0.022* | |
N4 | 0.40000 (11) | 0.72480 (10) | 0.24390 (9) | 0.0184 (2) | |
C5 | 0.34087 (13) | 0.62907 (12) | 0.29054 (11) | 0.0188 (3) | |
C6 | 0.22785 (13) | 0.65444 (11) | 0.36909 (10) | 0.0181 (3) | |
H6 | 0.1423 | 0.6368 | 0.3307 | 0.022* | |
S7 | 0.23985 (4) | 0.56073 (3) | 0.49162 (3) | 0.03100 (10) | |
C8 | 0.12233 (18) | 0.66080 (15) | 0.55673 (13) | 0.0343 (4) | |
H8A | 0.0312 | 0.6424 | 0.5316 | 0.041* | |
H8B | 0.1260 | 0.6523 | 0.6382 | 0.041* | |
C9 | 0.16183 (18) | 0.78775 (14) | 0.52223 (13) | 0.0347 (4) | |
H9A | 0.0830 | 0.8406 | 0.5184 | 0.042* | |
H9B | 0.2252 | 0.8225 | 0.5760 | 0.042* | |
C10 | 0.50501 (15) | 0.70247 (15) | 0.16278 (13) | 0.0295 (3) | |
H10A | 0.4654 | 0.6776 | 0.0923 | 0.044* | |
H10B | 0.5634 | 0.6384 | 0.1900 | 0.044* | |
H10C | 0.5565 | 0.7764 | 0.1517 | 0.044* | |
C11 | 0.26820 (14) | 0.89321 (12) | 0.15834 (11) | 0.0221 (3) | |
H11A | 0.2531 | 0.9811 | 0.1657 | 0.026* | |
H11B | 0.3170 | 0.8794 | 0.0884 | 0.026* | |
C12 | 0.13645 (14) | 0.83005 (11) | 0.15212 (11) | 0.0198 (3) | |
C13 | 0.02472 (15) | 0.88075 (14) | 0.20006 (13) | 0.0289 (3) | |
H13 | 0.0306 | 0.9581 | 0.2335 | 0.035* | |
C14 | −0.09570 (16) | 0.82002 (17) | 0.19984 (16) | 0.0376 (4) | |
H14 | −0.1716 | 0.8562 | 0.2323 | 0.045* | |
C15 | −0.10488 (15) | 0.70704 (15) | 0.15234 (14) | 0.0329 (4) | |
H15 | −0.1867 | 0.6648 | 0.1530 | 0.040* | |
C16 | 0.00535 (15) | 0.65563 (13) | 0.10387 (13) | 0.0278 (3) | |
H16 | −0.0008 | 0.5779 | 0.0712 | 0.033* | |
C17 | 0.12537 (14) | 0.71713 (12) | 0.10266 (11) | 0.0226 (3) | |
H17 | 0.2003 | 0.6818 | 0.0679 | 0.027* | |
O2 | 0.28006 (11) | 0.97279 (9) | 0.40579 (9) | 0.0306 (2) | |
O5 | 0.37353 (11) | 0.52417 (9) | 0.27289 (9) | 0.0301 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0259 (6) | 0.0164 (5) | 0.0208 (5) | 0.0033 (5) | 0.0063 (5) | 0.0013 (4) |
C2 | 0.0182 (6) | 0.0176 (6) | 0.0234 (6) | 0.0024 (5) | −0.0022 (5) | 0.0008 (5) |
C3 | 0.0157 (6) | 0.0158 (6) | 0.0225 (6) | −0.0022 (5) | 0.0001 (5) | 0.0035 (5) |
N4 | 0.0153 (5) | 0.0191 (5) | 0.0209 (5) | 0.0013 (4) | 0.0027 (4) | 0.0024 (4) |
C5 | 0.0177 (6) | 0.0182 (6) | 0.0206 (6) | 0.0002 (5) | −0.0006 (5) | 0.0004 (5) |
C6 | 0.0179 (6) | 0.0158 (6) | 0.0207 (6) | −0.0003 (5) | 0.0016 (5) | 0.0028 (4) |
S7 | 0.0407 (2) | 0.02351 (17) | 0.02876 (18) | 0.00466 (15) | 0.00626 (17) | 0.01102 (13) |
C8 | 0.0350 (9) | 0.0396 (9) | 0.0284 (7) | 0.0016 (7) | 0.0120 (7) | 0.0067 (7) |
C9 | 0.0461 (9) | 0.0297 (8) | 0.0282 (8) | 0.0073 (7) | 0.0175 (7) | 0.0015 (6) |
C10 | 0.0237 (8) | 0.0325 (8) | 0.0323 (8) | 0.0010 (6) | 0.0118 (6) | 0.0017 (7) |
C11 | 0.0222 (7) | 0.0206 (6) | 0.0234 (6) | −0.0015 (5) | −0.0015 (6) | 0.0078 (5) |
C12 | 0.0212 (6) | 0.0183 (6) | 0.0198 (6) | 0.0014 (5) | −0.0042 (5) | 0.0052 (5) |
C13 | 0.0248 (7) | 0.0219 (7) | 0.0398 (8) | 0.0041 (6) | −0.0025 (6) | −0.0045 (6) |
C14 | 0.0214 (7) | 0.0387 (9) | 0.0529 (10) | 0.0044 (7) | 0.0044 (7) | −0.0047 (8) |
C15 | 0.0222 (8) | 0.0319 (8) | 0.0447 (9) | −0.0048 (6) | −0.0064 (7) | 0.0062 (7) |
C16 | 0.0315 (8) | 0.0222 (7) | 0.0297 (7) | −0.0008 (6) | −0.0102 (6) | −0.0009 (6) |
C17 | 0.0240 (7) | 0.0231 (7) | 0.0206 (6) | 0.0034 (6) | −0.0025 (6) | −0.0002 (5) |
O2 | 0.0380 (6) | 0.0174 (5) | 0.0363 (5) | 0.0019 (4) | 0.0033 (5) | −0.0043 (4) |
O5 | 0.0313 (6) | 0.0168 (5) | 0.0423 (6) | 0.0033 (4) | 0.0092 (5) | −0.0022 (4) |
Geometric parameters (Å, º) top
N1—C2 | 1.3414 (17) | C9—H9B | 0.9900 |
N1—C6 | 1.4536 (16) | C10—H10A | 0.9800 |
N1—C9 | 1.4697 (18) | C10—H10B | 0.9800 |
C2—O2 | 1.2260 (16) | C10—H10C | 0.9800 |
C2—C3 | 1.5149 (18) | C11—C12 | 1.5054 (19) |
C3—N4 | 1.4647 (17) | C11—H11A | 0.9900 |
C3—C11 | 1.5498 (18) | C11—H11B | 0.9900 |
C3—H3 | 1.0000 | C12—C13 | 1.387 (2) |
N4—C5 | 1.3420 (17) | C12—C17 | 1.3919 (19) |
N4—C10 | 1.4651 (18) | C13—C14 | 1.390 (2) |
C5—O5 | 1.2278 (16) | C13—H13 | 0.9500 |
C5—C6 | 1.5108 (18) | C14—C15 | 1.381 (2) |
C6—S7 | 1.8128 (12) | C14—H14 | 0.9500 |
C6—H6 | 1.0000 | C15—C16 | 1.381 (2) |
S7—C8 | 1.8051 (17) | C15—H15 | 0.9500 |
C8—C9 | 1.521 (2) | C16—C17 | 1.391 (2) |
C8—H8A | 0.9900 | C16—H16 | 0.9500 |
C8—H8B | 0.9900 | C17—H17 | 0.9500 |
C9—H9A | 0.9900 | | |
| | | |
C2—N1—C6 | 124.31 (11) | N1—C9—H9B | 110.5 |
C2—N1—C9 | 120.67 (11) | C8—C9—H9B | 110.5 |
C6—N1—C9 | 114.62 (11) | H9A—C9—H9B | 108.7 |
O2—C2—N1 | 122.36 (12) | N4—C10—H10A | 109.5 |
O2—C2—C3 | 120.52 (12) | N4—C10—H10B | 109.5 |
N1—C2—C3 | 117.11 (11) | H10A—C10—H10B | 109.5 |
N4—C3—C2 | 113.11 (10) | N4—C10—H10C | 109.5 |
N4—C3—C11 | 113.08 (11) | H10A—C10—H10C | 109.5 |
C2—C3—C11 | 110.26 (11) | H10B—C10—H10C | 109.5 |
N4—C3—H3 | 106.6 | C12—C11—C3 | 112.87 (10) |
C2—C3—H3 | 106.6 | C12—C11—H11A | 109.0 |
C11—C3—H3 | 106.6 | C3—C11—H11A | 109.0 |
C5—N4—C3 | 124.21 (11) | C12—C11—H11B | 109.0 |
C5—N4—C10 | 117.99 (11) | C3—C11—H11B | 109.0 |
C3—N4—C10 | 117.21 (11) | H11A—C11—H11B | 107.8 |
O5—C5—N4 | 123.84 (13) | C13—C12—C17 | 118.58 (13) |
O5—C5—C6 | 119.24 (12) | C13—C12—C11 | 120.63 (12) |
N4—C5—C6 | 116.92 (11) | C17—C12—C11 | 120.72 (13) |
N1—C6—C5 | 114.99 (11) | C12—C13—C14 | 120.96 (14) |
N1—C6—S7 | 103.93 (8) | C12—C13—H13 | 119.5 |
C5—C6—S7 | 110.85 (9) | C14—C13—H13 | 119.5 |
N1—C6—H6 | 109.0 | C15—C14—C13 | 119.93 (15) |
C5—C6—H6 | 109.0 | C15—C14—H14 | 120.0 |
S7—C6—H6 | 109.0 | C13—C14—H14 | 120.0 |
C8—S7—C6 | 87.69 (6) | C16—C15—C14 | 119.77 (14) |
C9—C8—S7 | 106.08 (11) | C16—C15—H15 | 120.1 |
C9—C8—H8A | 110.5 | C14—C15—H15 | 120.1 |
S7—C8—H8A | 110.5 | C15—C16—C17 | 120.30 (14) |
C9—C8—H8B | 110.5 | C15—C16—H16 | 119.9 |
S7—C8—H8B | 110.5 | C17—C16—H16 | 119.9 |
H8A—C8—H8B | 108.7 | C16—C17—C12 | 120.44 (13) |
N1—C9—C8 | 106.29 (12) | C16—C17—H17 | 119.8 |
N1—C9—H9A | 110.5 | C12—C17—H17 | 119.8 |
C8—C9—H9A | 110.5 | | |
Crystal data top
C14H16N2O2S | Dx = 1.378 Mg m−3 |
Mr = 276.35 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 3930 reflections |
a = 7.7112 (7) Å | θ = 2.8–27.4° |
b = 11.6576 (12) Å | µ = 0.24 mm−1 |
c = 14.8171 (14) Å | T = 150 K |
V = 1332.0 (2) Å3 | Prism, colourless |
Z = 4 | 0.47 × 0.32 × 0.22 mm |
F(000) = 584 | |
Data collection top
Bruker APEX-II CCD diffractometer | 2789 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.047 |
φ and ω scans | θmax = 27.5°, θmin = 2.2° |
Absorption correction: multi-scan SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction | h = −10→6 |
Tmin = 0.895, Tmax = 0.948 | k = −15→14 |
8310 measured reflections | l = −19→17 |
3051 independent reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.035 | w = 1/[σ2(Fo2) + (0.0393P)2 + 0.0987P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.082 | (Δ/σ)max = 0.005 |
S = 1.04 | Δρmax = 0.28 e Å−3 |
3051 reflections | Δρmin = −0.22 e Å−3 |
173 parameters | Absolute structure: Flack x determined using 1085 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
0 restraints | Absolute structure parameter: −0.03 (5) |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.7342 (2) | 0.91146 (15) | 0.95285 (12) | 0.0172 (4) | |
C2 | 0.6237 (3) | 0.87146 (18) | 0.89056 (15) | 0.0171 (5) | |
C3 | 0.4971 (3) | 0.95500 (18) | 0.84832 (15) | 0.0173 (4) | |
H3 | 0.3783 | 0.9220 | 0.8562 | 0.021* | |
N4 | 0.4954 (2) | 1.06933 (16) | 0.88879 (12) | 0.0179 (4) | |
C5 | 0.6271 (3) | 1.11390 (19) | 0.93647 (15) | 0.0206 (5) | |
C6 | 0.7600 (3) | 1.03238 (18) | 0.97499 (15) | 0.0181 (4) | |
H6 | 0.7551 | 1.0395 | 1.0422 | 0.022* | |
C7 | 0.9456 (3) | 1.05934 (19) | 0.94594 (16) | 0.0211 (5) | |
H7A | 0.9877 | 1.1307 | 0.9748 | 0.025* | |
H7B | 0.9536 | 1.0676 | 0.8796 | 0.025* | |
S8 | 1.06830 (7) | 0.93579 (5) | 0.98469 (5) | 0.02899 (17) | |
C9 | 0.8777 (3) | 0.84158 (19) | 0.98550 (16) | 0.0211 (5) | |
H9A | 0.8963 | 0.7747 | 0.9455 | 0.025* | |
H9B | 0.8540 | 0.8135 | 1.0473 | 0.025* | |
C10 | 0.3559 (3) | 1.1466 (2) | 0.86001 (18) | 0.0249 (5) | |
H10A | 0.3948 | 1.1917 | 0.8080 | 0.037* | |
H10B | 0.3259 | 1.1984 | 0.9097 | 0.037* | |
H10C | 0.2538 | 1.1014 | 0.8431 | 0.037* | |
C11 | 0.5332 (2) | 0.96046 (19) | 0.74573 (15) | 0.0182 (5) | |
H11A | 0.5154 | 0.8833 | 0.7194 | 0.022* | |
H11B | 0.4486 | 1.0131 | 0.7173 | 0.022* | |
C12 | 0.7149 (3) | 1.00079 (19) | 0.72346 (14) | 0.0169 (5) | |
C13 | 0.8497 (3) | 0.9231 (2) | 0.71145 (14) | 0.0212 (5) | |
H13 | 0.8286 | 0.8435 | 0.7197 | 0.025* | |
C14 | 1.0150 (3) | 0.9601 (2) | 0.68745 (18) | 0.0260 (5) | |
H14 | 1.1055 | 0.9059 | 0.6787 | 0.031* | |
C15 | 1.0474 (3) | 1.0762 (2) | 0.67630 (15) | 0.0256 (5) | |
H15 | 1.1595 | 1.1017 | 0.6590 | 0.031* | |
C16 | 0.9155 (3) | 1.1546 (2) | 0.69046 (16) | 0.0256 (5) | |
H16 | 0.9383 | 1.2343 | 0.6846 | 0.031* | |
C17 | 0.7492 (3) | 1.1174 (2) | 0.71336 (15) | 0.0217 (5) | |
H17 | 0.6591 | 1.1719 | 0.7221 | 0.026* | |
O2 | 0.6208 (2) | 0.77031 (12) | 0.86597 (11) | 0.0235 (4) | |
O5 | 0.6384 (2) | 1.21630 (14) | 0.95518 (13) | 0.0335 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0156 (8) | 0.0167 (9) | 0.0194 (9) | 0.0033 (7) | 0.0011 (7) | −0.0001 (7) |
C2 | 0.0132 (10) | 0.0188 (11) | 0.0194 (12) | −0.0035 (8) | 0.0058 (8) | 0.0033 (9) |
C3 | 0.0122 (9) | 0.0162 (10) | 0.0234 (11) | −0.0028 (8) | 0.0002 (9) | 0.0001 (9) |
N4 | 0.0139 (8) | 0.0156 (9) | 0.0242 (10) | 0.0036 (7) | 0.0008 (7) | −0.0004 (8) |
C5 | 0.0165 (10) | 0.0232 (12) | 0.0221 (12) | 0.0040 (9) | 0.0029 (9) | −0.0054 (9) |
C6 | 0.0186 (10) | 0.0194 (11) | 0.0164 (10) | 0.0022 (8) | −0.0002 (8) | −0.0052 (9) |
C7 | 0.0165 (9) | 0.0194 (11) | 0.0273 (12) | 0.0029 (9) | −0.0036 (9) | 0.0002 (9) |
S8 | 0.0153 (2) | 0.0309 (3) | 0.0408 (4) | 0.0034 (2) | −0.0051 (2) | 0.0057 (3) |
C9 | 0.0195 (10) | 0.0223 (11) | 0.0213 (11) | 0.0054 (9) | 0.0012 (9) | 0.0023 (10) |
C10 | 0.0159 (10) | 0.0229 (12) | 0.0358 (14) | 0.0077 (9) | 0.0002 (10) | −0.0007 (11) |
C11 | 0.0134 (10) | 0.0206 (11) | 0.0205 (11) | −0.0017 (8) | −0.0036 (8) | −0.0015 (9) |
C12 | 0.0170 (10) | 0.0216 (11) | 0.0120 (10) | −0.0005 (9) | −0.0019 (9) | 0.0004 (9) |
C13 | 0.0183 (10) | 0.0236 (12) | 0.0218 (12) | 0.0001 (10) | −0.0015 (9) | 0.0001 (10) |
C14 | 0.0166 (11) | 0.0320 (14) | 0.0292 (13) | 0.0016 (10) | −0.0001 (10) | 0.0030 (10) |
C15 | 0.0168 (10) | 0.0361 (13) | 0.0238 (12) | −0.0065 (11) | −0.0004 (9) | 0.0070 (11) |
C16 | 0.0278 (13) | 0.0243 (12) | 0.0245 (12) | −0.0071 (10) | 0.0025 (10) | 0.0060 (10) |
C17 | 0.0226 (11) | 0.0230 (12) | 0.0196 (12) | 0.0011 (9) | 0.0004 (9) | 0.0031 (9) |
O2 | 0.0223 (8) | 0.0147 (8) | 0.0335 (9) | −0.0035 (6) | 0.0011 (7) | 0.0001 (7) |
O5 | 0.0285 (9) | 0.0200 (9) | 0.0521 (12) | 0.0071 (7) | −0.0072 (9) | −0.0141 (8) |
Geometric parameters (Å, º) top
N1—C2 | 1.340 (3) | C9—H9B | 0.9900 |
N1—C9 | 1.457 (3) | C10—H10A | 0.9800 |
N1—C6 | 1.461 (3) | C10—H10B | 0.9800 |
C2—O2 | 1.234 (3) | C10—H10C | 0.9800 |
C2—C3 | 1.514 (3) | C11—C12 | 1.514 (3) |
C3—N4 | 1.462 (3) | C11—H11A | 0.9900 |
C3—C11 | 1.547 (3) | C11—H11B | 0.9900 |
C3—H3 | 1.0000 | C12—C13 | 1.390 (3) |
N4—C5 | 1.342 (3) | C12—C17 | 1.394 (3) |
N4—C10 | 1.467 (3) | C13—C14 | 1.392 (3) |
C5—O5 | 1.229 (3) | C13—H13 | 0.9500 |
C5—C6 | 1.509 (3) | C14—C15 | 1.385 (3) |
C6—C7 | 1.527 (3) | C14—H14 | 0.9500 |
C6—H6 | 1.0000 | C15—C16 | 1.384 (3) |
C7—S8 | 1.817 (2) | C15—H15 | 0.9500 |
C7—H7A | 0.9900 | C16—C17 | 1.395 (3) |
C7—H7B | 0.9900 | C16—H16 | 0.9500 |
S8—C9 | 1.835 (2) | C17—H17 | 0.9500 |
C9—H9A | 0.9900 | | |
| | | |
C2—N1—C9 | 121.15 (18) | N1—C9—H9B | 110.6 |
C2—N1—C6 | 125.23 (17) | S8—C9—H9B | 110.6 |
C9—N1—C6 | 111.21 (17) | H9A—C9—H9B | 108.7 |
O2—C2—N1 | 123.2 (2) | N4—C10—H10A | 109.5 |
O2—C2—C3 | 118.7 (2) | N4—C10—H10B | 109.5 |
N1—C2—C3 | 118.10 (18) | H10A—C10—H10B | 109.5 |
N4—C3—C2 | 115.00 (18) | N4—C10—H10C | 109.5 |
N4—C3—C11 | 111.56 (17) | H10A—C10—H10C | 109.5 |
C2—C3—C11 | 108.45 (18) | H10B—C10—H10C | 109.5 |
N4—C3—H3 | 107.2 | C12—C11—C3 | 113.18 (18) |
C2—C3—H3 | 107.2 | C12—C11—H11A | 108.9 |
C11—C3—H3 | 107.2 | C3—C11—H11A | 108.9 |
C5—N4—C3 | 124.22 (18) | C12—C11—H11B | 108.9 |
C5—N4—C10 | 118.06 (18) | C3—C11—H11B | 108.9 |
C3—N4—C10 | 116.58 (18) | H11A—C11—H11B | 107.8 |
O5—C5—N4 | 123.3 (2) | C13—C12—C17 | 118.7 (2) |
O5—C5—C6 | 118.6 (2) | C13—C12—C11 | 121.2 (2) |
N4—C5—C6 | 117.97 (19) | C17—C12—C11 | 120.2 (2) |
N1—C6—C5 | 115.49 (18) | C12—C13—C14 | 121.0 (2) |
N1—C6—C7 | 105.23 (17) | C12—C13—H13 | 119.5 |
C5—C6—C7 | 113.57 (18) | C14—C13—H13 | 119.5 |
N1—C6—H6 | 107.4 | C15—C14—C13 | 119.9 (2) |
C5—C6—H6 | 107.4 | C15—C14—H14 | 120.1 |
C7—C6—H6 | 107.4 | C13—C14—H14 | 120.1 |
C6—C7—S8 | 103.65 (15) | C16—C15—C14 | 119.7 (2) |
C6—C7—H7A | 111.0 | C16—C15—H15 | 120.2 |
S8—C7—H7A | 111.0 | C14—C15—H15 | 120.2 |
C6—C7—H7B | 111.0 | C15—C16—C17 | 120.5 (2) |
S8—C7—H7B | 111.0 | C15—C16—H16 | 119.8 |
H7A—C7—H7B | 109.0 | C17—C16—H16 | 119.8 |
C7—S8—C9 | 93.40 (10) | C12—C17—C16 | 120.2 (2) |
N1—C9—S8 | 105.75 (14) | C12—C17—H17 | 119.9 |
N1—C9—H9A | 110.6 | C16—C17—H17 | 119.9 |
S8—C9—H9A | 110.6 | | |
Crystal data top
C14H16N2O2S | F(000) = 1752 |
Mr = 276.35 | Dx = 1.361 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 9979 reflections |
a = 13.4996 (5) Å | θ = 2.3–26.9° |
b = 14.5841 (5) Å | µ = 0.24 mm−1 |
c = 20.5461 (8) Å | T = 150 K |
V = 4045.1 (3) Å3 | Prism, colourless |
Z = 12 | 0.56 × 0.39 × 0.37 mm |
Data collection top
Bruker APEX-II CCD diffractometer | 8811 independent reflections |
Radiation source: fine-focus sealed tube | 7668 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
φ and ω scans | θmax = 27.0°, θmin = 1.7° |
Absorption correction: multi-scan SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction | h = −13→17 |
Tmin = 0.839, Tmax = 0.917 | k = −18→16 |
23583 measured reflections | l = −26→25 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.102 | w = 1/[σ2(Fo2) + (0.0533P)2 + 0.9427P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.003 |
8811 reflections | Δρmax = 0.39 e Å−3 |
517 parameters | Δρmin = −0.26 e Å−3 |
0 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.06 (5) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F2, conventional R-factors R are based
on F, with F set to zero for negative F2. The threshold expression of
F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F2 are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N11 | 0.60480 (14) | 0.32716 (12) | −0.07200 (9) | 0.0262 (4) | |
C21 | 0.58491 (17) | 0.30207 (14) | −0.13301 (10) | 0.0251 (4) | |
C31 | 0.48098 (17) | 0.26865 (15) | −0.14798 (10) | 0.0258 (4) | |
H31 | 0.4602 | 0.2985 | −0.1896 | 0.031* | |
N41 | 0.40698 (13) | 0.29299 (12) | −0.09876 (9) | 0.0264 (4) | |
C51 | 0.42813 (17) | 0.31012 (14) | −0.03634 (10) | 0.0269 (4) | |
C61 | 0.53587 (15) | 0.32280 (14) | −0.01736 (10) | 0.0244 (4) | |
H61 | 0.5560 | 0.2716 | 0.0122 | 0.029* | |
C71 | 0.54925 (16) | 0.41394 (14) | 0.01833 (11) | 0.0280 (4) | |
H71A | 0.5262 | 0.4090 | 0.0639 | 0.034* | |
H71B | 0.5116 | 0.4633 | −0.0036 | 0.034* | |
S81 | 0.68112 (5) | 0.43720 (4) | 0.01543 (3) | 0.03865 (15) | |
C91 | 0.70182 (17) | 0.36268 (17) | −0.05501 (12) | 0.0333 (5) | |
H91A | 0.7303 | 0.3979 | −0.0917 | 0.040* | |
H91B | 0.7476 | 0.3121 | −0.0438 | 0.040* | |
C101 | 0.30269 (17) | 0.28412 (17) | −0.11739 (12) | 0.0352 (5) | |
H10A | 0.2793 | 0.2222 | −0.1069 | 0.053* | |
H10B | 0.2958 | 0.2949 | −0.1642 | 0.053* | |
H10C | 0.2631 | 0.3292 | −0.0935 | 0.053* | |
C111 | 0.48490 (18) | 0.16381 (15) | −0.16082 (11) | 0.0299 (5) | |
H11A | 0.4194 | 0.1429 | −0.1765 | 0.036* | |
H11B | 0.5341 | 0.1511 | −0.1954 | 0.036* | |
C121 | 0.51231 (17) | 0.11065 (14) | −0.10070 (11) | 0.0280 (5) | |
C131 | 0.61036 (19) | 0.10116 (17) | −0.08142 (12) | 0.0366 (5) | |
H131 | 0.6616 | 0.1252 | −0.1081 | 0.044* | |
C141 | 0.63450 (19) | 0.05691 (19) | −0.02363 (13) | 0.0419 (6) | |
H141 | 0.7019 | 0.0516 | −0.0109 | 0.050* | |
C151 | 0.5611 (2) | 0.02076 (17) | 0.01526 (13) | 0.0419 (6) | |
H151 | 0.5777 | −0.0100 | 0.0545 | 0.050* | |
C161 | 0.4630 (2) | 0.02974 (18) | −0.00344 (12) | 0.0402 (6) | |
H161 | 0.4120 | 0.0053 | 0.0233 | 0.048* | |
C171 | 0.43891 (18) | 0.07419 (15) | −0.06084 (11) | 0.0319 (5) | |
H171 | 0.3714 | 0.0799 | −0.0732 | 0.038* | |
O21 | 0.64754 (12) | 0.30304 (11) | −0.17623 (7) | 0.0326 (4) | |
O51 | 0.36396 (12) | 0.31954 (12) | 0.00598 (8) | 0.0363 (4) | |
N12 | 0.35662 (15) | −0.17699 (13) | −0.08737 (9) | 0.0293 (4) | |
C22 | 0.40428 (19) | −0.19563 (15) | −0.03202 (10) | 0.0316 (5) | |
C32 | 0.5139 (2) | −0.21435 (18) | −0.03580 (11) | 0.0379 (6) | |
H32 | 0.5458 | −0.1801 | 0.0008 | 0.045* | |
N42 | 0.56056 (15) | −0.18232 (14) | −0.09646 (10) | 0.0363 (5) | |
C52 | 0.51233 (19) | −0.16795 (17) | −0.15212 (11) | 0.0341 (5) | |
C62 | 0.40045 (18) | −0.17579 (15) | −0.15235 (10) | 0.0290 (5) | |
H62 | 0.3813 | −0.2333 | −0.1757 | 0.035* | |
C72 | 0.35293 (18) | −0.09420 (16) | −0.18677 (11) | 0.0346 (5) | |
H72A | 0.3578 | −0.1010 | −0.2346 | 0.041* | |
H72B | 0.3857 | −0.0362 | −0.1738 | 0.041* | |
S82 | 0.22375 (5) | −0.09506 (4) | −0.16072 (3) | 0.03748 (14) | |
C92 | 0.25013 (18) | −0.16048 (17) | −0.08686 (12) | 0.0349 (5) | |
H92A | 0.2308 | −0.1251 | −0.0477 | 0.042* | |
H92B | 0.2134 | −0.2192 | −0.0870 | 0.042* | |
C102 | 0.6689 (2) | −0.1749 (2) | −0.09628 (15) | 0.0508 (7) | |
H10D | 0.6979 | −0.2321 | −0.1125 | 0.076* | |
H10E | 0.6921 | −0.1635 | −0.0518 | 0.076* | |
H10F | 0.6892 | −0.1240 | −0.1244 | 0.076* | |
C112 | 0.5330 (2) | −0.31743 (18) | −0.02376 (13) | 0.0416 (6) | |
H11C | 0.6052 | −0.3288 | −0.0245 | 0.050* | |
H11D | 0.5084 | −0.3338 | 0.0201 | 0.050* | |
C122 | 0.48358 (18) | −0.37890 (16) | −0.07339 (11) | 0.0333 (5) | |
C132 | 0.38367 (18) | −0.40155 (16) | −0.06889 (11) | 0.0326 (5) | |
H132 | 0.3453 | −0.3785 | −0.0338 | 0.039* | |
C142 | 0.3395 (2) | −0.45759 (16) | −0.11535 (12) | 0.0369 (5) | |
H142 | 0.2714 | −0.4731 | −0.1115 | 0.044* | |
C152 | 0.3944 (2) | −0.49074 (17) | −0.16709 (12) | 0.0422 (6) | |
H152 | 0.3642 | −0.5286 | −0.1991 | 0.051* | |
C162 | 0.4932 (2) | −0.46846 (18) | −0.17187 (13) | 0.0468 (7) | |
H162 | 0.5313 | −0.4912 | −0.2072 | 0.056* | |
C172 | 0.5377 (2) | −0.41291 (18) | −0.12535 (13) | 0.0424 (6) | |
H172 | 0.6060 | −0.3981 | −0.1292 | 0.051* | |
O22 | 0.36184 (14) | −0.20075 (13) | 0.02087 (8) | 0.0428 (4) | |
O52 | 0.55408 (14) | −0.14734 (15) | −0.20364 (9) | 0.0491 (5) | |
N13 | 0.53199 (13) | 0.37714 (12) | 0.29698 (8) | 0.0255 (4) | |
C23 | 0.44281 (17) | 0.34175 (14) | 0.31160 (10) | 0.0268 (4) | |
C33 | 0.38564 (17) | 0.29795 (14) | 0.25687 (10) | 0.0268 (4) | |
H33 | 0.3548 | 0.2412 | 0.2751 | 0.032* | |
N43 | 0.44733 (13) | 0.26897 (12) | 0.20248 (9) | 0.0256 (4) | |
C53 | 0.53506 (16) | 0.30643 (14) | 0.18708 (10) | 0.0248 (4) | |
C63 | 0.57306 (15) | 0.38195 (14) | 0.23116 (10) | 0.0245 (4) | |
H63 | 0.5557 | 0.4427 | 0.2116 | 0.029* | |
C73 | 0.68418 (17) | 0.37675 (15) | 0.23994 (12) | 0.0319 (5) | |
H73A | 0.7191 | 0.3987 | 0.2005 | 0.038* | |
H73B | 0.7055 | 0.3132 | 0.2494 | 0.038* | |
S83 | 0.70814 (5) | 0.45137 (5) | 0.30873 (3) | 0.04241 (16) | |
C93 | 0.59071 (18) | 0.42212 (16) | 0.34718 (11) | 0.0335 (5) | |
H93A | 0.6015 | 0.3804 | 0.3845 | 0.040* | |
H93B | 0.5568 | 0.4781 | 0.3630 | 0.040* | |
C103 | 0.40747 (19) | 0.19818 (17) | 0.15918 (12) | 0.0371 (5) | |
H10G | 0.3971 | 0.2242 | 0.1157 | 0.056* | |
H10H | 0.3442 | 0.1759 | 0.1765 | 0.056* | |
H10I | 0.4545 | 0.1471 | 0.1564 | 0.056* | |
C113 | 0.29966 (16) | 0.36076 (15) | 0.23529 (11) | 0.0293 (5) | |
H11E | 0.2606 | 0.3291 | 0.2012 | 0.035* | |
H11F | 0.2554 | 0.3719 | 0.2729 | 0.035* | |
C123 | 0.33569 (15) | 0.45208 (14) | 0.20894 (11) | 0.0261 (4) | |
C133 | 0.35170 (18) | 0.52535 (16) | 0.25129 (12) | 0.0333 (5) | |
H133 | 0.3377 | 0.5185 | 0.2963 | 0.040* | |
C143 | 0.3879 (2) | 0.60818 (16) | 0.22804 (13) | 0.0413 (6) | |
H143 | 0.3984 | 0.6576 | 0.2573 | 0.050* | |
C153 | 0.4086 (2) | 0.61926 (17) | 0.16313 (14) | 0.0418 (6) | |
H153 | 0.4333 | 0.6761 | 0.1474 | 0.050* | |
C163 | 0.39291 (18) | 0.54662 (17) | 0.12048 (12) | 0.0364 (5) | |
H163 | 0.4072 | 0.5537 | 0.0755 | 0.044* | |
C173 | 0.35638 (16) | 0.46356 (15) | 0.14363 (11) | 0.0294 (5) | |
H173 | 0.3456 | 0.4143 | 0.1142 | 0.035* | |
O23 | 0.40791 (14) | 0.34572 (12) | 0.36696 (8) | 0.0392 (4) | |
O53 | 0.58457 (12) | 0.28290 (11) | 0.14017 (7) | 0.0326 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N11 | 0.0215 (9) | 0.0263 (9) | 0.0307 (9) | −0.0007 (7) | 0.0025 (7) | 0.0001 (7) |
C21 | 0.0289 (12) | 0.0178 (9) | 0.0287 (10) | 0.0038 (8) | 0.0051 (9) | 0.0038 (8) |
C31 | 0.0294 (12) | 0.0239 (10) | 0.0241 (10) | 0.0023 (9) | 0.0004 (8) | 0.0021 (8) |
N41 | 0.0228 (9) | 0.0243 (9) | 0.0320 (9) | 0.0000 (7) | 0.0007 (7) | 0.0003 (7) |
C51 | 0.0272 (12) | 0.0214 (10) | 0.0320 (11) | 0.0007 (8) | 0.0024 (9) | 0.0010 (8) |
C61 | 0.0238 (11) | 0.0237 (10) | 0.0259 (10) | 0.0016 (8) | 0.0020 (8) | 0.0016 (8) |
C71 | 0.0265 (11) | 0.0249 (10) | 0.0325 (11) | 0.0032 (8) | −0.0003 (9) | −0.0015 (8) |
S81 | 0.0301 (3) | 0.0359 (3) | 0.0499 (4) | −0.0037 (3) | −0.0030 (3) | −0.0115 (3) |
C91 | 0.0240 (12) | 0.0365 (12) | 0.0395 (13) | −0.0029 (9) | 0.0020 (9) | −0.0074 (10) |
C101 | 0.0256 (12) | 0.0377 (13) | 0.0424 (13) | 0.0010 (10) | −0.0053 (10) | −0.0020 (10) |
C111 | 0.0375 (13) | 0.0235 (11) | 0.0288 (10) | −0.0023 (9) | 0.0022 (9) | −0.0027 (8) |
C121 | 0.0329 (12) | 0.0207 (10) | 0.0306 (11) | 0.0005 (9) | 0.0051 (9) | −0.0038 (8) |
C131 | 0.0341 (13) | 0.0300 (12) | 0.0456 (13) | 0.0042 (10) | 0.0119 (11) | 0.0090 (10) |
C141 | 0.0295 (12) | 0.0424 (14) | 0.0538 (15) | 0.0061 (11) | 0.0006 (11) | 0.0132 (12) |
C151 | 0.0467 (15) | 0.0364 (13) | 0.0426 (13) | 0.0027 (11) | 0.0002 (12) | 0.0129 (11) |
C161 | 0.0415 (15) | 0.0381 (13) | 0.0408 (13) | −0.0027 (11) | 0.0076 (11) | 0.0091 (10) |
C171 | 0.0291 (12) | 0.0294 (12) | 0.0373 (12) | −0.0044 (9) | 0.0024 (9) | 0.0015 (9) |
O21 | 0.0319 (9) | 0.0330 (8) | 0.0328 (8) | 0.0044 (7) | 0.0084 (7) | 0.0043 (6) |
O51 | 0.0280 (9) | 0.0445 (10) | 0.0364 (9) | −0.0017 (7) | 0.0080 (7) | −0.0071 (7) |
N12 | 0.0326 (10) | 0.0283 (9) | 0.0270 (9) | −0.0047 (8) | 0.0047 (8) | −0.0016 (7) |
C22 | 0.0453 (14) | 0.0248 (11) | 0.0247 (11) | −0.0095 (10) | 0.0014 (9) | −0.0022 (8) |
C32 | 0.0433 (15) | 0.0434 (14) | 0.0270 (11) | −0.0121 (12) | −0.0058 (10) | 0.0012 (10) |
N42 | 0.0315 (11) | 0.0405 (12) | 0.0369 (11) | −0.0109 (9) | 0.0014 (9) | 0.0023 (8) |
C52 | 0.0371 (13) | 0.0390 (13) | 0.0261 (11) | −0.0085 (11) | 0.0033 (10) | −0.0040 (9) |
C62 | 0.0329 (12) | 0.0290 (11) | 0.0252 (10) | −0.0067 (9) | 0.0019 (9) | −0.0038 (8) |
C72 | 0.0434 (14) | 0.0280 (11) | 0.0323 (11) | −0.0069 (10) | 0.0003 (10) | −0.0008 (9) |
S82 | 0.0400 (3) | 0.0305 (3) | 0.0419 (3) | 0.0015 (3) | −0.0029 (3) | −0.0031 (2) |
C92 | 0.0365 (13) | 0.0319 (12) | 0.0364 (13) | −0.0007 (10) | 0.0051 (10) | −0.0019 (9) |
C102 | 0.0315 (14) | 0.0625 (19) | 0.0584 (17) | −0.0129 (13) | −0.0045 (13) | 0.0036 (14) |
C112 | 0.0373 (14) | 0.0443 (14) | 0.0431 (14) | −0.0034 (11) | −0.0127 (11) | 0.0103 (11) |
C122 | 0.0350 (13) | 0.0278 (12) | 0.0369 (12) | 0.0042 (10) | −0.0066 (10) | 0.0097 (9) |
C132 | 0.0340 (13) | 0.0298 (11) | 0.0341 (11) | 0.0020 (10) | −0.0009 (9) | 0.0046 (9) |
C142 | 0.0380 (14) | 0.0309 (12) | 0.0419 (13) | 0.0021 (11) | −0.0047 (10) | 0.0028 (10) |
C152 | 0.0574 (17) | 0.0274 (12) | 0.0419 (13) | 0.0052 (12) | −0.0009 (12) | 0.0010 (10) |
C162 | 0.0579 (18) | 0.0351 (14) | 0.0475 (15) | 0.0149 (12) | 0.0140 (13) | 0.0003 (11) |
C172 | 0.0338 (14) | 0.0396 (14) | 0.0538 (15) | 0.0083 (11) | 0.0090 (11) | 0.0070 (12) |
O22 | 0.0560 (12) | 0.0462 (10) | 0.0262 (8) | −0.0116 (9) | 0.0059 (8) | −0.0037 (7) |
O52 | 0.0411 (10) | 0.0729 (13) | 0.0333 (9) | −0.0158 (10) | 0.0074 (8) | −0.0012 (9) |
N13 | 0.0259 (9) | 0.0244 (9) | 0.0262 (9) | −0.0027 (7) | −0.0032 (7) | 0.0007 (7) |
C23 | 0.0313 (11) | 0.0234 (10) | 0.0258 (10) | 0.0006 (9) | 0.0013 (9) | 0.0025 (8) |
C33 | 0.0279 (11) | 0.0194 (10) | 0.0331 (11) | −0.0055 (8) | 0.0020 (9) | 0.0011 (8) |
N43 | 0.0257 (9) | 0.0195 (8) | 0.0315 (9) | −0.0016 (7) | −0.0013 (8) | −0.0041 (7) |
C53 | 0.0269 (11) | 0.0215 (10) | 0.0261 (10) | 0.0031 (8) | −0.0047 (8) | 0.0044 (8) |
C63 | 0.0229 (10) | 0.0212 (10) | 0.0294 (10) | −0.0002 (8) | −0.0005 (8) | 0.0018 (8) |
C73 | 0.0258 (11) | 0.0274 (11) | 0.0424 (13) | −0.0008 (9) | −0.0014 (10) | −0.0059 (9) |
S83 | 0.0290 (3) | 0.0448 (4) | 0.0534 (4) | −0.0071 (3) | −0.0060 (3) | −0.0126 (3) |
C93 | 0.0377 (13) | 0.0319 (12) | 0.0308 (11) | −0.0049 (10) | −0.0053 (10) | −0.0021 (9) |
C103 | 0.0356 (13) | 0.0297 (12) | 0.0459 (13) | −0.0033 (10) | −0.0026 (11) | −0.0130 (10) |
C113 | 0.0232 (11) | 0.0263 (10) | 0.0386 (12) | −0.0039 (9) | 0.0015 (9) | −0.0034 (9) |
C123 | 0.0180 (10) | 0.0216 (10) | 0.0387 (11) | 0.0021 (8) | −0.0018 (8) | −0.0040 (8) |
C133 | 0.0327 (13) | 0.0296 (12) | 0.0377 (12) | 0.0005 (10) | −0.0004 (10) | −0.0069 (9) |
C143 | 0.0408 (14) | 0.0244 (12) | 0.0586 (16) | −0.0016 (10) | −0.0051 (12) | −0.0125 (11) |
C153 | 0.0367 (14) | 0.0259 (12) | 0.0628 (16) | 0.0003 (10) | 0.0040 (12) | 0.0050 (11) |
C163 | 0.0339 (13) | 0.0339 (12) | 0.0415 (13) | 0.0079 (11) | 0.0025 (10) | 0.0063 (10) |
C173 | 0.0235 (11) | 0.0300 (11) | 0.0346 (12) | 0.0063 (9) | −0.0023 (9) | −0.0050 (9) |
O23 | 0.0445 (11) | 0.0421 (10) | 0.0309 (8) | −0.0064 (8) | 0.0079 (8) | 0.0000 (7) |
O53 | 0.0312 (9) | 0.0349 (9) | 0.0316 (8) | 0.0012 (7) | 0.0028 (7) | −0.0029 (6) |
Geometric parameters (Å, º) top
N11—C21 | 1.333 (3) | C92—H92B | 0.9900 |
N11—C91 | 1.451 (3) | C102—H10D | 0.9800 |
N11—C61 | 1.460 (3) | C102—H10E | 0.9800 |
C21—O21 | 1.226 (3) | C102—H10F | 0.9800 |
C21—C31 | 1.517 (3) | C112—C122 | 1.513 (3) |
C31—N41 | 1.465 (3) | C112—H11C | 0.9900 |
C31—C111 | 1.553 (3) | C112—H11D | 0.9900 |
C31—H31 | 1.0000 | C122—C172 | 1.385 (3) |
N41—C51 | 1.337 (3) | C122—C132 | 1.392 (3) |
N41—C101 | 1.465 (3) | C132—C142 | 1.391 (3) |
C51—O51 | 1.235 (3) | C132—H132 | 0.9500 |
C51—C61 | 1.517 (3) | C142—C152 | 1.383 (4) |
C61—C71 | 1.529 (3) | C142—H142 | 0.9500 |
C61—H61 | 1.0000 | C152—C162 | 1.376 (4) |
C71—S81 | 1.813 (2) | C152—H152 | 0.9500 |
C71—H71A | 0.9900 | C162—C172 | 1.390 (4) |
C71—H71B | 0.9900 | C162—H162 | 0.9500 |
S81—C91 | 1.831 (2) | C172—H172 | 0.9500 |
C91—H91A | 0.9900 | N13—C23 | 1.344 (3) |
C91—H91B | 0.9900 | N13—C93 | 1.457 (3) |
C101—H10A | 0.9800 | N13—C63 | 1.463 (3) |
C101—H10B | 0.9800 | C23—O23 | 1.232 (3) |
C101—H10C | 0.9800 | C23—C33 | 1.506 (3) |
C111—C121 | 1.505 (3) | C33—N43 | 1.456 (3) |
C111—H11A | 0.9900 | C33—C113 | 1.544 (3) |
C111—H11B | 0.9900 | C33—H33 | 1.0000 |
C121—C131 | 1.389 (3) | N43—C53 | 1.342 (3) |
C121—C171 | 1.391 (3) | N43—C103 | 1.465 (3) |
C131—C141 | 1.390 (3) | C53—O53 | 1.222 (3) |
C131—H131 | 0.9500 | C53—C63 | 1.516 (3) |
C141—C151 | 1.377 (4) | C63—C73 | 1.513 (3) |
C141—H141 | 0.9500 | C63—H63 | 1.0000 |
C151—C161 | 1.386 (4) | C73—S83 | 1.813 (2) |
C151—H151 | 0.9500 | C73—H73A | 0.9900 |
C161—C171 | 1.384 (3) | C73—H73B | 0.9900 |
C161—H161 | 0.9500 | S83—C93 | 1.822 (3) |
C171—H171 | 0.9500 | C93—H93A | 0.9900 |
N12—C22 | 1.335 (3) | C93—H93B | 0.9900 |
N12—C92 | 1.458 (3) | C103—H10G | 0.9800 |
N12—C62 | 1.460 (3) | C103—H10H | 0.9800 |
C22—O22 | 1.231 (3) | C103—H10I | 0.9800 |
C22—C32 | 1.507 (4) | C113—C123 | 1.518 (3) |
C32—N42 | 1.472 (3) | C113—H11E | 0.9900 |
C32—C112 | 1.545 (4) | C113—H11F | 0.9900 |
C32—H32 | 1.0000 | C123—C173 | 1.381 (3) |
N42—C52 | 1.333 (3) | C123—C133 | 1.395 (3) |
N42—C102 | 1.467 (3) | C133—C143 | 1.388 (3) |
C52—O52 | 1.236 (3) | C133—H133 | 0.9500 |
C52—C62 | 1.515 (3) | C143—C153 | 1.372 (4) |
C62—C72 | 1.526 (3) | C143—H143 | 0.9500 |
C62—H62 | 1.0000 | C153—C163 | 1.391 (4) |
C72—S82 | 1.824 (3) | C153—H153 | 0.9500 |
C72—H72A | 0.9900 | C163—C173 | 1.392 (3) |
C72—H72B | 0.9900 | C163—H163 | 0.9500 |
S82—C92 | 1.828 (2) | C173—H173 | 0.9500 |
C92—H92A | 0.9900 | | |
| | | |
C21—N11—C91 | 120.39 (18) | N12—C92—H92B | 110.6 |
C21—N11—C61 | 125.65 (18) | S82—C92—H92B | 110.6 |
C91—N11—C61 | 113.96 (17) | H92A—C92—H92B | 108.7 |
O21—C21—N11 | 122.6 (2) | N42—C102—H10D | 109.5 |
O21—C21—C31 | 119.65 (19) | N42—C102—H10E | 109.5 |
N11—C21—C31 | 117.72 (18) | H10D—C102—H10E | 109.5 |
N41—C31—C21 | 114.38 (17) | N42—C102—H10F | 109.5 |
N41—C31—C111 | 112.29 (18) | H10D—C102—H10F | 109.5 |
C21—C31—C111 | 108.63 (18) | H10E—C102—H10F | 109.5 |
N41—C31—H31 | 107.1 | C122—C112—C32 | 113.29 (19) |
C21—C31—H31 | 107.1 | C122—C112—H11C | 108.9 |
C111—C31—H31 | 107.1 | C32—C112—H11C | 108.9 |
C51—N41—C101 | 118.18 (18) | C122—C112—H11D | 108.9 |
C51—N41—C31 | 124.17 (18) | C32—C112—H11D | 108.9 |
C101—N41—C31 | 116.97 (18) | H11C—C112—H11D | 107.7 |
O51—C51—N41 | 123.1 (2) | C172—C122—C132 | 118.5 (2) |
O51—C51—C61 | 118.54 (19) | C172—C122—C112 | 120.0 (2) |
N41—C51—C61 | 118.29 (18) | C132—C122—C112 | 121.5 (2) |
N11—C61—C51 | 114.75 (17) | C142—C132—C122 | 120.6 (2) |
N11—C61—C71 | 104.82 (17) | C142—C132—H132 | 119.7 |
C51—C61—C71 | 110.03 (17) | C122—C132—H132 | 119.7 |
N11—C61—H61 | 109.0 | C152—C142—C132 | 120.2 (3) |
C51—C61—H61 | 109.0 | C152—C142—H142 | 119.9 |
C71—C61—H61 | 109.0 | C132—C142—H142 | 119.9 |
C61—C71—S81 | 105.24 (14) | C162—C152—C142 | 119.5 (3) |
C61—C71—H71A | 110.7 | C162—C152—H152 | 120.3 |
S81—C71—H71A | 110.7 | C142—C152—H152 | 120.3 |
C61—C71—H71B | 110.7 | C152—C162—C172 | 120.5 (2) |
S81—C71—H71B | 110.7 | C152—C162—H162 | 119.8 |
H71A—C71—H71B | 108.8 | C172—C162—H162 | 119.8 |
C71—S81—C91 | 93.71 (10) | C122—C172—C162 | 120.7 (3) |
N11—C91—S81 | 105.32 (15) | C122—C172—H172 | 119.6 |
N11—C91—H91A | 110.7 | C162—C172—H172 | 119.6 |
S81—C91—H91A | 110.7 | C23—N13—C93 | 120.15 (18) |
N11—C91—H91B | 110.7 | C23—N13—C63 | 124.36 (17) |
S81—C91—H91B | 110.7 | C93—N13—C63 | 115.24 (17) |
H91A—C91—H91B | 108.8 | O23—C23—N13 | 122.0 (2) |
N41—C101—H10A | 109.5 | O23—C23—C33 | 120.9 (2) |
N41—C101—H10B | 109.5 | N13—C23—C33 | 117.07 (18) |
H10A—C101—H10B | 109.5 | N43—C33—C23 | 113.77 (18) |
N41—C101—H10C | 109.5 | N43—C33—C113 | 112.44 (17) |
H10A—C101—H10C | 109.5 | C23—C33—C113 | 110.38 (18) |
H10B—C101—H10C | 109.5 | N43—C33—H33 | 106.6 |
C121—C111—C31 | 112.10 (18) | C23—C33—H33 | 106.6 |
C121—C111—H11A | 109.2 | C113—C33—H33 | 106.6 |
C31—C111—H11A | 109.2 | C53—N43—C33 | 124.57 (18) |
C121—C111—H11B | 109.2 | C53—N43—C103 | 117.88 (19) |
C31—C111—H11B | 109.2 | C33—N43—C103 | 117.41 (18) |
H11A—C111—H11B | 107.9 | O53—C53—N43 | 123.7 (2) |
C131—C121—C171 | 118.2 (2) | O53—C53—C63 | 119.36 (19) |
C131—C121—C111 | 121.3 (2) | N43—C53—C63 | 116.98 (18) |
C171—C121—C111 | 120.3 (2) | N13—C63—C73 | 105.26 (17) |
C121—C131—C141 | 120.9 (2) | N13—C63—C53 | 112.90 (17) |
C121—C131—H131 | 119.6 | C73—C63—C53 | 111.75 (17) |
C141—C131—H131 | 119.6 | N13—C63—H63 | 108.9 |
C151—C141—C131 | 120.3 (2) | C73—C63—H63 | 108.9 |
C151—C141—H141 | 119.8 | C53—C63—H63 | 108.9 |
C131—C141—H141 | 119.8 | C63—C73—S83 | 103.87 (15) |
C141—C151—C161 | 119.4 (2) | C63—C73—H73A | 111.0 |
C141—C151—H151 | 120.3 | S83—C73—H73A | 111.0 |
C161—C151—H151 | 120.3 | C63—C73—H73B | 111.0 |
C171—C161—C151 | 120.3 (2) | S83—C73—H73B | 111.0 |
C171—C161—H161 | 119.8 | H73A—C73—H73B | 109.0 |
C151—C161—H161 | 119.8 | C73—S83—C93 | 92.42 (10) |
C161—C171—C121 | 120.9 (2) | N13—C93—S83 | 105.79 (15) |
C161—C171—H171 | 119.6 | N13—C93—H93A | 110.6 |
C121—C171—H171 | 119.6 | S83—C93—H93A | 110.6 |
C22—N12—C92 | 120.20 (19) | N13—C93—H93B | 110.6 |
C22—N12—C62 | 125.9 (2) | S83—C93—H93B | 110.6 |
C92—N12—C62 | 113.85 (19) | H93A—C93—H93B | 108.7 |
O22—C22—N12 | 122.7 (2) | N43—C103—H10G | 109.5 |
O22—C22—C32 | 119.4 (2) | N43—C103—H10H | 109.5 |
N12—C22—C32 | 117.8 (2) | H10G—C103—H10H | 109.5 |
N42—C32—C22 | 114.0 (2) | N43—C103—H10I | 109.5 |
N42—C32—C112 | 111.9 (2) | H10G—C103—H10I | 109.5 |
C22—C32—C112 | 109.3 (2) | H10H—C103—H10I | 109.5 |
N42—C32—H32 | 107.1 | C123—C113—C33 | 112.47 (17) |
C22—C32—H32 | 107.1 | C123—C113—H11E | 109.1 |
C112—C32—H32 | 107.1 | C33—C113—H11E | 109.1 |
C52—N42—C102 | 118.5 (2) | C123—C113—H11F | 109.1 |
C52—N42—C32 | 124.6 (2) | C33—C113—H11F | 109.1 |
C102—N42—C32 | 116.6 (2) | H11E—C113—H11F | 107.8 |
O52—C52—N42 | 123.4 (2) | C173—C123—C133 | 118.8 (2) |
O52—C52—C62 | 118.1 (2) | C173—C123—C113 | 121.19 (19) |
N42—C52—C62 | 118.5 (2) | C133—C123—C113 | 120.0 (2) |
N12—C62—C52 | 113.72 (19) | C143—C133—C123 | 120.4 (2) |
N12—C62—C72 | 105.23 (18) | C143—C133—H133 | 119.8 |
C52—C62—C72 | 111.21 (19) | C123—C133—H133 | 119.8 |
N12—C62—H62 | 108.8 | C153—C143—C133 | 120.6 (2) |
C52—C62—H62 | 108.8 | C153—C143—H143 | 119.7 |
C72—C62—H62 | 108.8 | C133—C143—H143 | 119.7 |
C62—C72—S82 | 105.10 (15) | C143—C153—C163 | 119.5 (2) |
C62—C72—H72A | 110.7 | C143—C153—H153 | 120.3 |
S82—C72—H72A | 110.7 | C163—C153—H153 | 120.3 |
C62—C72—H72B | 110.7 | C153—C163—C173 | 120.1 (2) |
S82—C72—H72B | 110.7 | C153—C163—H163 | 120.0 |
H72A—C72—H72B | 108.8 | C173—C163—H163 | 120.0 |
C72—S82—C92 | 93.49 (11) | C123—C173—C163 | 120.6 (2) |
N12—C92—S82 | 105.81 (16) | C123—C173—H173 | 119.7 |
N12—C92—H92A | 110.6 | C163—C173—H173 | 119.7 |
S82—C92—H92A | 110.6 | | |
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