To compare the structural properties of oxalamide and thiooxalamide groups in the formation of hydrogen bonds suitable for supramolecular assemblies a series of retropeptides was studied. Some of them, having oxalamide bridges, are gelators of organic solvents and water. However, retropeptides with oxygen replaced by the sp2 sulfur have not exhibited such properties. The crystal structures of the two title compounds are homostructural, i.e. they have similar packing arrangements. The monothio compound crystallizes in the orthorhombic space group P212121 with two molecules in the asymmetric unit arranged in a hydrogen-bond network with an approximate 41 axis along the crystallographic b axis. However, the dithio and dioxo analogues crystallize in the tetragonal space group P41 with similar packing patterns and hydrogen-bonding systems arranged in agreement with a crystallographic 41 axis. Thus, these two analogues are isostructural having closely related hydrogen-bonding patterns in spite of the different size and polarity of oxygen and sulfur which serve as the proton acceptors.
Supporting information
CCDC references: 230851; 230852
Data collection: CAD-4 EXPRESS (Enraf Nonius, 1994) for (I); Collect (Nonius BV, 1997-2000) for (II). Cell refinement: CAD-4 EXPRESS (Enraf Nonius, 1994) for (I); HKL SCALEPACK (Otwinowski & Minor 1997) for (II). Data reduction: XCAD4 (Harms & Wocadlo, 1995) for (I); HKL DENZO and SCALEPACK (Otwinowski & Minor 1997) for (II). For both compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997). Software used to prepare material for publication: PLATON (Spek, 1990) for (I); WinGX publication routines (Farrugia, 1999) for (II).
(I)
N,
N'-monotiooxalyl-bis(
L-leucine methyl ester)
top
Crystal data top
C16H28N2O5S | F(000) = 1552 |
Mr = 360.46 | Dx = 1.119 Mg m−3 |
Orthorhombic, P212121 | Cu Kα radiation, λ = 1.54128 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 20 reflections |
a = 12.562 (9) Å | θ = 9–19° |
b = 16.156 (5) Å | µ = 1.55 mm−1 |
c = 21.086 (8) Å | T = 293 K |
V = 4279 (4) Å3 | Prism, yellow |
Z = 8 | 0.4 × 0.2 × 0.15 mm |
Data collection top
Enraf Nonius CAD4 diffractometer | Rint = 0.035 |
non–profiled ω/2θ scans | θmax = 76.4°, θmin = 3.5° |
Absorption correction: ψ scan North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
Number of ψ scan sets used was 7
Theta correction was applied.
Averaged transmission function was used.
No Fourier smoothing was applied. | h = 0→15 |
Tmin = 0.752, Tmax = 0.791 | k = 0→20 |
9699 measured reflections | l = −26→26 |
8972 independent reflections | 3 standard reflections every 120 min |
4033 reflections with I > 2σ(I) | intensity decay: 5% |
Refinement top
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0634P)2 + 0.8826P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.060 | (Δ/σ)max = 0.002 |
wR(F2) = 0.174 | Δρmax = 0.24 e Å−3 |
S = 1.01 | Δρmin = −0.16 e Å−3 |
8972 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
433 parameters | Absolute structure parameter: −0.01 (3) |
0 restraints | |
Crystal data top
C16H28N2O5S | V = 4279 (4) Å3 |
Mr = 360.46 | Z = 8 |
Orthorhombic, P212121 | Cu Kα radiation |
a = 12.562 (9) Å | µ = 1.55 mm−1 |
b = 16.156 (5) Å | T = 293 K |
c = 21.086 (8) Å | 0.4 × 0.2 × 0.15 mm |
Data collection top
Enraf Nonius CAD4 diffractometer | 4033 reflections with I > 2σ(I) |
Absorption correction: ψ scan North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
Number of ψ scan sets used was 7
Theta correction was applied.
Averaged transmission function was used.
No Fourier smoothing was applied. | Rint = 0.035 |
Tmin = 0.752, Tmax = 0.791 | 3 standard reflections every 120 min |
9699 measured reflections | intensity decay: 5% |
8972 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.060 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.174 | Δρmax = 0.24 e Å−3 |
S = 1.01 | Δρmin = −0.16 e Å−3 |
8972 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
433 parameters | Absolute structure parameter: −0.01 (3) |
0 restraints | |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S11 | 0.97619 (12) | 0.33587 (8) | 0.31144 (6) | 0.0933 (4) | |
O1 | 0.8294 (3) | 0.54782 (19) | 0.30879 (13) | 0.0828 (9) | |
O2 | 0.6739 (3) | 0.3967 (3) | 0.1880 (2) | 0.1227 (14) | |
O3 | 0.6221 (3) | 0.5235 (3) | 0.16328 (18) | 0.1195 (13) | |
O21 | 0.8128 (4) | 0.4070 (3) | 0.4880 (2) | 0.1411 (16) | |
O31 | 0.9370 (4) | 0.3190 (3) | 0.5193 (2) | 0.1386 (16) | |
N1 | 0.8671 (3) | 0.4609 (2) | 0.22801 (16) | 0.0703 (10) | |
H1 | 0.9031 | 0.4184 | 0.2161 | 0.084* | |
N11 | 0.9405 (3) | 0.4588 (2) | 0.38999 (16) | 0.0786 (11) | |
H11 | 0.9164 | 0.508 | 0.3957 | 0.094* | |
C1 | 0.8703 (3) | 0.4839 (3) | 0.2881 (2) | 0.0602 (10) | |
C2 | 0.8042 (4) | 0.5057 (3) | 0.1815 (2) | 0.0741 (12) | |
H2 | 0.7985 | 0.5638 | 0.1943 | 0.089* | |
C3 | 0.6939 (4) | 0.4676 (4) | 0.1787 (2) | 0.0856 (14) | |
C4 | 0.5132 (5) | 0.4929 (5) | 0.1574 (4) | 0.159 (3) | |
H41 | 0.467 | 0.5378 | 0.1459 | 0.238* | |
H42 | 0.4907 | 0.47 | 0.1972 | 0.238* | |
H43 | 0.5105 | 0.4509 | 0.1253 | 0.238* | |
C5 | 0.8534 (4) | 0.5005 (3) | 0.1158 (2) | 0.0837 (14) | |
H51 | 0.8658 | 0.4427 | 0.1058 | 0.1* | |
H52 | 0.8023 | 0.5216 | 0.0853 | 0.1* | |
C6 | 0.9563 (5) | 0.5469 (4) | 0.1076 (3) | 0.1129 (19) | |
H6 | 1.0055 | 0.5292 | 0.141 | 0.135* | |
C7 | 1.0055 (7) | 0.5247 (6) | 0.0431 (4) | 0.189 (4) | |
H71 | 1.0713 | 0.5542 | 0.0378 | 0.284* | |
H72 | 0.9572 | 0.5399 | 0.0098 | 0.284* | |
H73 | 1.0188 | 0.4663 | 0.0414 | 0.284* | |
C8 | 0.9416 (6) | 0.6393 (4) | 0.1128 (4) | 0.176 (3) | |
H81 | 1.0092 | 0.6663 | 0.1077 | 0.264* | |
H82 | 0.9129 | 0.6525 | 0.1538 | 0.264* | |
H83 | 0.8936 | 0.6578 | 0.0804 | 0.264* | |
C11 | 0.9317 (3) | 0.4263 (2) | 0.3326 (2) | 0.0618 (11) | |
C21 | 0.9881 (4) | 0.4170 (3) | 0.4440 (2) | 0.0828 (13) | |
H21 | 1.0324 | 0.3716 | 0.428 | 0.099* | |
C31 | 0.9021 (6) | 0.3804 (4) | 0.4848 (3) | 0.0954 (16) | |
C41 | 0.8611 (7) | 0.2828 (5) | 0.5639 (4) | 0.180 (4) | |
H411 | 0.8948 | 0.2385 | 0.5867 | 0.271* | |
H412 | 0.8009 | 0.2617 | 0.541 | 0.271* | |
H413 | 0.8379 | 0.3244 | 0.5933 | 0.271* | |
C51 | 1.0583 (5) | 0.4747 (3) | 0.4818 (2) | 0.1011 (17) | |
H511 | 1.0866 | 0.4444 | 0.5178 | 0.121* | |
H512 | 1.0143 | 0.519 | 0.4985 | 0.121* | |
C61 | 1.1511 (6) | 0.5134 (5) | 0.4463 (3) | 0.131 (2) | |
H61 | 1.1218 | 0.5419 | 0.4091 | 0.157* | |
C71 | 1.2049 (8) | 0.5783 (5) | 0.4875 (5) | 0.202 (4) | |
H711 | 1.1527 | 0.6169 | 0.5026 | 0.303* | |
H712 | 1.2575 | 0.6072 | 0.4629 | 0.303* | |
H713 | 1.2387 | 0.5518 | 0.5229 | 0.303* | |
C81 | 1.2280 (7) | 0.4490 (7) | 0.4226 (4) | 0.187 (4) | |
H811 | 1.1903 | 0.4089 | 0.3976 | 0.281* | |
H812 | 1.2611 | 0.422 | 0.458 | 0.281* | |
H813 | 1.2815 | 0.4751 | 0.397 | 0.281* | |
S13 | 0.88969 (11) | 0.09017 (8) | 0.23114 (8) | 0.1045 (5) | |
O12 | 0.9117 (2) | 0.30274 (19) | 0.14608 (15) | 0.0815 (9) | |
O22 | 1.0976 (4) | 0.1287 (2) | 0.05469 (16) | 0.1258 (15) | |
O23 | 0.6028 (5) | 0.1787 (5) | 0.1320 (3) | 0.195 (3) | |
O32 | 1.2046 (5) | 0.2287 (3) | 0.0290 (2) | 0.172 (2) | |
O33 | 0.5314 (4) | 0.0995 (3) | 0.2026 (3) | 0.180 (2) | |
N12 | 1.0372 (3) | 0.2054 (2) | 0.16303 (16) | 0.0692 (10) | |
H12 | 1.0516 | 0.1607 | 0.1835 | 0.083* | |
N13 | 0.7671 (3) | 0.2173 (2) | 0.20851 (18) | 0.0823 (11) | |
H13 | 0.7611 | 0.2668 | 0.1939 | 0.099* | |
C12 | 0.9395 (4) | 0.2359 (3) | 0.16768 (19) | 0.0646 (11) | |
C13 | 0.8603 (4) | 0.1819 (3) | 0.20357 (19) | 0.0663 (11) | |
C22 | 1.1200 (3) | 0.2424 (3) | 0.1260 (2) | 0.0715 (12) | |
H22 | 1.0976 | 0.2983 | 0.1139 | 0.086* | |
C23 | 0.6733 (4) | 0.1806 (3) | 0.2364 (3) | 0.0937 (15) | |
H23 | 0.6951 | 0.132 | 0.261 | 0.112* | |
C32 | 1.1375 (5) | 0.1926 (3) | 0.0667 (2) | 0.0937 (16) | |
C33 | 0.5988 (6) | 0.1522 (5) | 0.1837 (5) | 0.128 (2) | |
C42 | 1.2292 (9) | 0.1851 (6) | −0.0306 (4) | 0.238 (6) | |
H421 | 1.2794 | 0.217 | −0.0547 | 0.356* | |
H422 | 1.1651 | 0.1781 | −0.0547 | 0.356* | |
H423 | 1.2591 | 0.1319 | −0.0211 | 0.356* | |
C43 | 0.4556 (7) | 0.0778 (7) | 0.1509 (6) | 0.267 (7) | |
H431 | 0.4045 | 0.0385 | 0.1665 | 0.4* | |
H432 | 0.494 | 0.054 | 0.116 | 0.4* | |
H433 | 0.4193 | 0.1268 | 0.137 | 0.4* | |
C52 | 1.2238 (4) | 0.2486 (3) | 0.1633 (3) | 0.0893 (15) | |
H521 | 1.2409 | 0.1942 | 0.1797 | 0.107* | |
H522 | 1.28 | 0.2641 | 0.1341 | 0.107* | |
C53 | 0.6160 (4) | 0.2404 (4) | 0.2807 (3) | 0.1057 (17) | |
H531 | 0.5936 | 0.2883 | 0.2564 | 0.127* | |
H532 | 0.5524 | 0.2136 | 0.2967 | 0.127* | |
C62 | 1.2244 (5) | 0.3078 (5) | 0.2167 (3) | 0.124 (2) | |
H62 | 1.1626 | 0.2961 | 0.2436 | 0.149* | |
C63 | 0.6815 (5) | 0.2698 (5) | 0.3364 (3) | 0.129 (2) | |
H63 | 0.7482 | 0.2919 | 0.3192 | 0.155* | |
C72 | 1.3251 (6) | 0.2984 (6) | 0.2569 (4) | 0.195 (4) | |
H721 | 1.3236 | 0.3378 | 0.291 | 0.292* | |
H722 | 1.3866 | 0.3081 | 0.231 | 0.292* | |
H723 | 1.3281 | 0.2434 | 0.2741 | 0.292* | |
C73 | 0.6222 (7) | 0.3424 (6) | 0.3678 (4) | 0.203 (4) | |
H731 | 0.6619 | 0.3614 | 0.4039 | 0.304* | |
H732 | 0.553 | 0.3242 | 0.3813 | 0.304* | |
H733 | 0.6145 | 0.3867 | 0.3379 | 0.304* | |
C82 | 1.2170 (7) | 0.3956 (4) | 0.1945 (4) | 0.184 (4) | |
H821 | 1.2172 | 0.4319 | 0.2306 | 0.275* | |
H822 | 1.1522 | 0.4031 | 0.171 | 0.275* | |
H823 | 1.2767 | 0.4081 | 0.1678 | 0.275* | |
C83 | 0.7104 (7) | 0.2020 (7) | 0.3817 (4) | 0.188 (4) | |
H831 | 0.751 | 0.2247 | 0.4162 | 0.281* | |
H832 | 0.752 | 0.161 | 0.3601 | 0.281* | |
H833 | 0.6467 | 0.1771 | 0.398 | 0.281* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S11 | 0.1154 (10) | 0.0755 (8) | 0.0890 (8) | 0.0199 (8) | −0.0116 (8) | −0.0128 (7) |
O1 | 0.112 (2) | 0.0697 (18) | 0.0671 (17) | 0.0213 (18) | −0.0075 (18) | −0.0096 (16) |
O2 | 0.088 (2) | 0.102 (3) | 0.178 (4) | −0.007 (2) | −0.017 (3) | 0.019 (3) |
O3 | 0.100 (3) | 0.128 (3) | 0.130 (3) | 0.023 (3) | −0.020 (2) | 0.030 (3) |
O21 | 0.129 (4) | 0.163 (4) | 0.132 (3) | 0.024 (3) | 0.017 (3) | 0.046 (3) |
O31 | 0.154 (4) | 0.119 (3) | 0.143 (4) | 0.010 (3) | −0.013 (3) | 0.055 (3) |
N1 | 0.083 (3) | 0.065 (2) | 0.063 (2) | 0.0101 (19) | −0.004 (2) | −0.0099 (19) |
N11 | 0.107 (3) | 0.065 (2) | 0.063 (2) | 0.018 (2) | −0.011 (2) | −0.0063 (19) |
C1 | 0.058 (3) | 0.058 (3) | 0.064 (3) | −0.005 (2) | 0.002 (2) | 0.002 (2) |
C2 | 0.088 (3) | 0.067 (3) | 0.067 (3) | 0.010 (3) | −0.007 (3) | 0.002 (2) |
C3 | 0.092 (4) | 0.096 (4) | 0.069 (3) | 0.005 (4) | −0.009 (3) | 0.011 (3) |
C4 | 0.084 (4) | 0.220 (8) | 0.172 (6) | 0.015 (5) | −0.041 (4) | 0.013 (6) |
C5 | 0.102 (4) | 0.077 (3) | 0.072 (3) | −0.004 (3) | −0.003 (3) | 0.004 (2) |
C6 | 0.092 (4) | 0.138 (5) | 0.109 (4) | −0.010 (4) | 0.015 (3) | 0.000 (4) |
C7 | 0.170 (7) | 0.238 (9) | 0.159 (7) | −0.027 (7) | 0.078 (6) | −0.001 (7) |
C8 | 0.173 (7) | 0.103 (5) | 0.251 (10) | −0.057 (5) | 0.017 (7) | 0.010 (5) |
C11 | 0.061 (3) | 0.057 (2) | 0.067 (3) | −0.010 (2) | 0.003 (2) | 0.002 (2) |
C21 | 0.097 (4) | 0.081 (3) | 0.070 (3) | 0.020 (3) | −0.012 (3) | 0.002 (3) |
C31 | 0.108 (5) | 0.096 (4) | 0.082 (4) | 0.011 (4) | 0.001 (4) | 0.014 (3) |
C41 | 0.182 (8) | 0.173 (7) | 0.186 (7) | −0.030 (6) | 0.001 (6) | 0.106 (6) |
C51 | 0.123 (5) | 0.096 (4) | 0.085 (3) | 0.001 (4) | −0.031 (4) | 0.007 (3) |
C61 | 0.128 (6) | 0.152 (6) | 0.112 (5) | −0.018 (5) | −0.035 (5) | 0.014 (5) |
C71 | 0.194 (8) | 0.174 (7) | 0.239 (10) | −0.067 (7) | −0.079 (8) | 0.002 (7) |
C81 | 0.127 (6) | 0.263 (11) | 0.172 (7) | −0.012 (7) | 0.006 (6) | −0.030 (8) |
S13 | 0.0988 (10) | 0.0828 (9) | 0.1318 (11) | 0.0093 (8) | 0.0268 (9) | 0.0293 (8) |
O12 | 0.082 (2) | 0.070 (2) | 0.093 (2) | 0.0120 (17) | 0.0012 (17) | 0.0160 (17) |
O22 | 0.212 (5) | 0.092 (3) | 0.073 (2) | −0.039 (3) | 0.010 (3) | −0.003 (2) |
O23 | 0.156 (5) | 0.268 (7) | 0.163 (5) | −0.072 (5) | −0.028 (5) | −0.017 (5) |
O32 | 0.241 (6) | 0.128 (3) | 0.148 (4) | −0.060 (4) | 0.116 (4) | −0.036 (3) |
O33 | 0.123 (4) | 0.191 (5) | 0.227 (6) | −0.076 (4) | 0.020 (4) | −0.046 (5) |
N12 | 0.070 (2) | 0.066 (2) | 0.072 (2) | 0.005 (2) | 0.009 (2) | 0.0116 (17) |
N13 | 0.069 (3) | 0.080 (2) | 0.099 (3) | 0.001 (2) | 0.006 (2) | 0.012 (2) |
C12 | 0.071 (3) | 0.062 (3) | 0.060 (3) | 0.003 (2) | −0.002 (2) | −0.004 (2) |
C13 | 0.065 (3) | 0.073 (3) | 0.061 (3) | 0.000 (2) | −0.004 (2) | 0.000 (2) |
C22 | 0.071 (3) | 0.062 (3) | 0.082 (3) | −0.003 (2) | 0.009 (3) | 0.000 (2) |
C23 | 0.070 (3) | 0.098 (4) | 0.113 (4) | −0.007 (3) | 0.010 (3) | 0.009 (3) |
C32 | 0.131 (5) | 0.066 (3) | 0.084 (4) | −0.012 (3) | 0.024 (3) | −0.001 (3) |
C33 | 0.089 (5) | 0.135 (6) | 0.162 (7) | −0.022 (4) | 0.023 (6) | −0.025 (6) |
C42 | 0.381 (15) | 0.191 (8) | 0.142 (6) | −0.056 (9) | 0.165 (8) | −0.057 (6) |
C43 | 0.151 (8) | 0.267 (12) | 0.383 (16) | −0.033 (8) | −0.023 (10) | −0.175 (13) |
C52 | 0.073 (3) | 0.080 (3) | 0.114 (4) | 0.002 (3) | 0.015 (3) | 0.004 (3) |
C53 | 0.081 (4) | 0.112 (4) | 0.124 (4) | −0.008 (3) | 0.029 (4) | 0.000 (4) |
C62 | 0.091 (4) | 0.176 (7) | 0.107 (4) | 0.001 (4) | 0.000 (4) | −0.039 (5) |
C63 | 0.091 (4) | 0.166 (6) | 0.130 (6) | −0.034 (5) | 0.010 (4) | −0.029 (5) |
C72 | 0.148 (6) | 0.262 (10) | 0.175 (7) | −0.040 (7) | −0.066 (6) | −0.022 (7) |
C73 | 0.187 (8) | 0.203 (8) | 0.218 (9) | −0.026 (8) | 0.043 (7) | −0.104 (7) |
C82 | 0.183 (7) | 0.100 (5) | 0.268 (10) | 0.023 (5) | −0.078 (7) | −0.083 (6) |
C83 | 0.175 (8) | 0.253 (11) | 0.135 (6) | 0.002 (8) | −0.020 (6) | 0.025 (7) |
Geometric parameters (Å, º) top
S11—C11 | 1.627 (4) | S13—C13 | 1.634 (4) |
O1—C1 | 1.233 (5) | O12—C12 | 1.223 (5) |
O2—C3 | 1.189 (6) | O22—C32 | 1.175 (6) |
O3—C3 | 1.318 (6) | O23—C33 | 1.174 (8) |
O3—C4 | 1.459 (7) | O32—C32 | 1.297 (6) |
O21—C31 | 1.203 (6) | O32—C42 | 1.472 (7) |
O31—C31 | 1.305 (6) | O33—C33 | 1.264 (8) |
O31—C41 | 1.461 (8) | O33—C43 | 1.489 (10) |
N1—C1 | 1.322 (5) | N12—C12 | 1.326 (5) |
N1—C2 | 1.452 (5) | N12—C22 | 1.431 (5) |
N1—H1 | 0.86 | N12—H12 | 0.86 |
N11—C11 | 1.324 (5) | N13—C13 | 1.307 (5) |
N11—C21 | 1.452 (5) | N13—C23 | 1.445 (6) |
N11—H11 | 0.86 | N13—H13 | 0.86 |
C1—C11 | 1.529 (6) | C12—C13 | 1.525 (6) |
C2—C3 | 1.517 (7) | C22—C32 | 1.505 (7) |
C2—C5 | 1.520 (6) | C22—C52 | 1.525 (6) |
C2—H2 | 0.98 | C22—H22 | 0.98 |
C4—H41 | 0.96 | C23—C33 | 1.524 (10) |
C4—H42 | 0.96 | C23—C53 | 1.524 (7) |
C4—H43 | 0.96 | C23—H23 | 0.98 |
C5—C6 | 1.505 (7) | C42—H421 | 0.96 |
C5—H51 | 0.97 | C42—H422 | 0.96 |
C5—H52 | 0.97 | C42—H423 | 0.96 |
C6—C8 | 1.507 (9) | C43—H431 | 0.96 |
C6—C7 | 1.536 (8) | C43—H432 | 0.96 |
C6—H6 | 0.98 | C43—H433 | 0.96 |
C7—H71 | 0.96 | C52—C62 | 1.477 (7) |
C7—H72 | 0.96 | C52—H521 | 0.97 |
C7—H73 | 0.96 | C52—H522 | 0.97 |
C8—H81 | 0.96 | C53—C63 | 1.509 (8) |
C8—H82 | 0.96 | C53—H531 | 0.97 |
C8—H83 | 0.96 | C53—H532 | 0.97 |
C21—C31 | 1.504 (7) | C62—C82 | 1.497 (9) |
C21—C51 | 1.512 (7) | C62—C72 | 1.531 (9) |
C21—H21 | 0.98 | C62—H62 | 0.98 |
C41—H411 | 0.96 | C63—C83 | 1.498 (10) |
C41—H412 | 0.96 | C63—C73 | 1.540 (9) |
C41—H413 | 0.96 | C63—H63 | 0.98 |
C51—C61 | 1.519 (8) | C72—H721 | 0.96 |
C51—H511 | 0.97 | C72—H722 | 0.96 |
C51—H512 | 0.97 | C72—H723 | 0.96 |
C61—C81 | 1.505 (9) | C73—H731 | 0.96 |
C61—C71 | 1.520 (9) | C73—H732 | 0.96 |
C61—H61 | 0.98 | C73—H733 | 0.96 |
C71—H711 | 0.96 | C82—H821 | 0.96 |
C71—H712 | 0.96 | C82—H822 | 0.96 |
C71—H713 | 0.96 | C82—H823 | 0.96 |
C81—H811 | 0.96 | C83—H831 | 0.96 |
C81—H812 | 0.96 | C83—H832 | 0.96 |
C81—H813 | 0.96 | C83—H833 | 0.96 |
| | | |
C3—O3—C4 | 115.5 (5) | C32—O32—C42 | 116.3 (5) |
C31—O31—C41 | 116.3 (5) | C33—O33—C43 | 110.9 (8) |
C1—N1—C2 | 121.6 (4) | C12—N12—C22 | 123.9 (4) |
C1—N1—H1 | 119.2 | C12—N12—H12 | 118.1 |
C2—N1—H1 | 119.2 | C22—N12—H12 | 118.1 |
C11—N11—C21 | 124.6 (4) | C13—N13—C23 | 125.7 (4) |
C11—N11—H11 | 117.7 | C13—N13—H13 | 117.2 |
C21—N11—H11 | 117.7 | C23—N13—H13 | 117.2 |
O1—C1—N1 | 124.2 (4) | O12—C12—N12 | 124.4 (4) |
O1—C1—C11 | 120.2 (4) | O12—C12—C13 | 120.2 (4) |
N1—C1—C11 | 115.6 (4) | N12—C12—C13 | 115.3 (4) |
N1—C2—C3 | 108.7 (4) | N13—C13—C12 | 111.9 (4) |
N1—C2—C5 | 111.5 (4) | N13—C13—S13 | 124.8 (3) |
C3—C2—C5 | 108.2 (4) | C12—C13—S13 | 123.2 (3) |
N1—C2—H2 | 109.4 | N12—C22—C32 | 109.6 (4) |
C3—C2—H2 | 109.4 | N12—C22—C52 | 111.6 (4) |
C5—C2—H2 | 109.4 | C32—C22—C52 | 109.8 (4) |
O2—C3—O3 | 123.8 (5) | N12—C22—H22 | 108.6 |
O2—C3—C2 | 125.3 (5) | C32—C22—H22 | 108.6 |
O3—C3—C2 | 110.9 (5) | C52—C22—H22 | 108.6 |
O3—C4—H41 | 109.5 | N13—C23—C33 | 109.1 (5) |
O3—C4—H42 | 109.5 | N13—C23—C53 | 112.0 (4) |
H41—C4—H42 | 109.5 | C33—C23—C53 | 110.4 (5) |
O3—C4—H43 | 109.5 | N13—C23—H23 | 108.4 |
H41—C4—H43 | 109.5 | C33—C23—H23 | 108.4 |
H42—C4—H43 | 109.5 | C53—C23—H23 | 108.4 |
C6—C5—C2 | 115.2 (4) | O22—C32—O32 | 122.7 (5) |
C6—C5—H51 | 108.5 | O22—C32—C22 | 125.9 (5) |
C2—C5—H51 | 108.5 | O32—C32—C22 | 111.3 (5) |
C6—C5—H52 | 108.5 | O23—C33—O33 | 124.5 (9) |
C2—C5—H52 | 108.5 | O23—C33—C23 | 122.8 (7) |
H51—C5—H52 | 107.5 | O33—C33—C23 | 112.7 (8) |
C8—C6—C5 | 112.3 (5) | O32—C42—H421 | 109.5 |
C8—C6—C7 | 110.2 (6) | O32—C42—H422 | 109.5 |
C5—C6—C7 | 109.3 (5) | H421—C42—H422 | 109.5 |
C8—C6—H6 | 108.3 | O32—C42—H423 | 109.5 |
C5—C6—H6 | 108.3 | H421—C42—H423 | 109.5 |
C7—C6—H6 | 108.3 | H422—C42—H423 | 109.5 |
C6—C7—H71 | 109.5 | O33—C43—H431 | 109.5 |
C6—C7—H72 | 109.5 | O33—C43—H432 | 109.5 |
H71—C7—H72 | 109.5 | H431—C43—H432 | 109.5 |
C6—C7—H73 | 109.5 | O33—C43—H433 | 109.5 |
H71—C7—H73 | 109.5 | H431—C43—H433 | 109.5 |
H72—C7—H73 | 109.5 | H432—C43—H433 | 109.5 |
C6—C8—H81 | 109.5 | C62—C52—C22 | 116.1 (4) |
C6—C8—H82 | 109.5 | C62—C52—H521 | 108.3 |
H81—C8—H82 | 109.5 | C22—C52—H521 | 108.3 |
C6—C8—H83 | 109.5 | C62—C52—H522 | 108.3 |
H81—C8—H83 | 109.5 | C22—C52—H522 | 108.3 |
H82—C8—H83 | 109.5 | H521—C52—H522 | 107.4 |
N11—C11—C1 | 111.2 (3) | C63—C53—C23 | 114.7 (5) |
N11—C11—S11 | 125.3 (3) | C63—C53—H531 | 108.6 |
C1—C11—S11 | 123.5 (3) | C23—C53—H531 | 108.6 |
N11—C21—C31 | 109.6 (4) | C63—C53—H532 | 108.6 |
N11—C21—C51 | 111.5 (4) | C23—C53—H532 | 108.6 |
C31—C21—C51 | 111.1 (4) | H531—C53—H532 | 107.6 |
N11—C21—H21 | 108.2 | C52—C62—C82 | 112.0 (6) |
C31—C21—H21 | 108.2 | C52—C62—C72 | 111.3 (6) |
C51—C21—H21 | 108.2 | C82—C62—C72 | 108.5 (7) |
O21—C31—O31 | 123.6 (6) | C52—C62—H62 | 108.3 |
O21—C31—C21 | 124.2 (5) | C82—C62—H62 | 108.3 |
O31—C31—C21 | 112.1 (5) | C72—C62—H62 | 108.3 |
O31—C41—H411 | 109.5 | C83—C63—C53 | 113.5 (6) |
O31—C41—H412 | 109.5 | C83—C63—C73 | 113.5 (7) |
H411—C41—H412 | 109.5 | C53—C63—C73 | 108.1 (7) |
O31—C41—H413 | 109.5 | C83—C63—H63 | 107.1 |
H411—C41—H413 | 109.5 | C53—C63—H63 | 107.1 |
H412—C41—H413 | 109.5 | C73—C63—H63 | 107.1 |
C21—C51—C61 | 116.1 (5) | C62—C72—H721 | 109.5 |
C21—C51—H511 | 108.3 | C62—C72—H722 | 109.5 |
C61—C51—H511 | 108.3 | H721—C72—H722 | 109.5 |
C21—C51—H512 | 108.3 | C62—C72—H723 | 109.5 |
C61—C51—H512 | 108.3 | H721—C72—H723 | 109.5 |
H511—C51—H512 | 107.4 | H722—C72—H723 | 109.5 |
C81—C61—C51 | 111.9 (6) | C63—C73—H731 | 109.5 |
C81—C61—C71 | 112.4 (7) | C63—C73—H732 | 109.5 |
C51—C61—C71 | 110.1 (7) | H731—C73—H732 | 109.5 |
C81—C61—H61 | 107.4 | C63—C73—H733 | 109.5 |
C51—C61—H61 | 107.4 | H731—C73—H733 | 109.5 |
C71—C61—H61 | 107.4 | H732—C73—H733 | 109.5 |
C61—C71—H711 | 109.5 | C62—C82—H821 | 109.5 |
C61—C71—H712 | 109.5 | C62—C82—H822 | 109.5 |
H711—C71—H712 | 109.5 | H821—C82—H822 | 109.5 |
C61—C71—H713 | 109.5 | C62—C82—H823 | 109.5 |
H711—C71—H713 | 109.5 | H821—C82—H823 | 109.5 |
H712—C71—H713 | 109.5 | H822—C82—H823 | 109.5 |
C61—C81—H811 | 109.5 | C63—C83—H831 | 109.5 |
C61—C81—H812 | 109.5 | C63—C83—H832 | 109.5 |
H811—C81—H812 | 109.5 | H831—C83—H832 | 109.5 |
C61—C81—H813 | 109.5 | C63—C83—H833 | 109.5 |
H811—C81—H813 | 109.5 | H831—C83—H833 | 109.5 |
H812—C81—H813 | 109.5 | H832—C83—H833 | 109.5 |
| | | |
C2—N1—C1—O1 | −6.6 (6) | C22—N12—C12—O12 | −7.2 (7) |
C2—N1—C1—C11 | 174.7 (3) | C22—N12—C12—C13 | 173.6 (4) |
C1—N1—C2—C3 | −90.8 (5) | C23—N13—C13—C12 | 176.2 (4) |
C1—N1—C2—C5 | 149.9 (4) | C23—N13—C13—S13 | −2.9 (7) |
C4—O3—C3—O2 | −0.6 (8) | O12—C12—C13—N13 | −1.9 (6) |
C4—O3—C3—C2 | 178.3 (5) | N12—C12—C13—N13 | 177.4 (4) |
N1—C2—C3—O2 | −31.1 (7) | O12—C12—C13—S13 | 177.2 (3) |
C5—C2—C3—O2 | 90.2 (6) | N12—C12—C13—S13 | −3.5 (5) |
N1—C2—C3—O3 | 150.0 (4) | C12—N12—C22—C32 | −105.5 (5) |
C5—C2—C3—O3 | −88.6 (5) | C12—N12—C22—C52 | 132.6 (4) |
N1—C2—C5—C6 | −69.2 (5) | C13—N13—C23—C33 | −102.7 (6) |
C3—C2—C5—C6 | 171.2 (5) | C13—N13—C23—C53 | 134.8 (5) |
C2—C5—C6—C8 | −66.5 (7) | C42—O32—C32—O22 | −0.2 (11) |
C2—C5—C6—C7 | 170.8 (5) | C42—O32—C32—C22 | 179.3 (7) |
C21—N11—C11—C1 | 175.7 (4) | N12—C22—C32—O22 | −6.9 (8) |
C21—N11—C11—S11 | −2.5 (6) | C52—C22—C32—O22 | 116.1 (7) |
O1—C1—C11—N11 | −5.6 (5) | N12—C22—C32—O32 | 173.6 (5) |
N1—C1—C11—N11 | 173.1 (4) | C52—C22—C32—O32 | −63.4 (6) |
O1—C1—C11—S11 | 172.5 (3) | C43—O33—C33—O23 | −1.9 (12) |
N1—C1—C11—S11 | −8.7 (5) | C43—O33—C33—C23 | 176.1 (6) |
C11—N11—C21—C31 | −98.7 (5) | N13—C23—C33—O23 | −21.1 (10) |
C11—N11—C21—C51 | 137.8 (5) | C53—C23—C33—O23 | 102.4 (9) |
C41—O31—C31—O21 | −0.4 (9) | N13—C23—C33—O33 | 161.0 (5) |
C41—O31—C31—C21 | 176.0 (6) | C53—C23—C33—O33 | −75.6 (7) |
N11—C21—C31—O21 | −26.9 (8) | N12—C22—C52—C62 | −68.7 (6) |
C51—C21—C31—O21 | 96.8 (7) | C32—C22—C52—C62 | 169.5 (5) |
N11—C21—C31—O31 | 156.7 (4) | N13—C23—C53—C63 | −60.6 (7) |
C51—C21—C31—O31 | −79.6 (6) | C33—C23—C53—C63 | 177.6 (6) |
N11—C21—C51—C61 | −59.5 (6) | C22—C52—C62—C82 | −67.7 (7) |
C31—C21—C51—C61 | 177.9 (5) | C22—C52—C62—C72 | 170.6 (5) |
C21—C51—C61—C81 | −62.0 (7) | C23—C53—C63—C83 | −64.9 (7) |
C21—C51—C61—C71 | 172.3 (5) | C23—C53—C63—C73 | 168.3 (5) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O12 | 0.86 | 2.38 | 3.135 (5) | 146 |
N1—H1···S11 | 0.86 | 2.58 | 3.009 (4) | 112 |
N11—H11···O22i | 0.86 | 2.22 | 3.021 (5) | 155 |
N12—H12···O1ii | 0.86 | 2.36 | 3.105 (5) | 145 |
N12—H12···S13 | 0.86 | 2.54 | 2.993 (4) | 114 |
N13—H13···O2 | 0.86 | 2.37 | 3.155 (6) | 152 |
N11—H11···O1 | 0.86 | 2.23 | 2.636 (5) | 109 |
N13—H13···O12 | 0.86 | 2.22 | 2.634 (5) | 109 |
Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) −x+2, y−1/2, −z+1/2. |
(II)
N,
N'-ditiooxalyl-bis(
L-leucine methyl ester)
top
Crystal data top
C16H28N2O4S2 | Dx = 1.207 Mg m−3 |
Mr = 376.52 | Mo Kα radiation, λ = 0.71069 Å |
Tetragonal, P41 | Cell parameters from 1504 reflections |
Hall symbol: P 4w | θ = 2.6–23.0° |
a = 11.3877 (4) Å | µ = 0.27 mm−1 |
c = 15.9829 (6) Å | T = 293 K |
V = 2072.66 (13) Å3 | Prism, yellow |
Z = 4 | 0.5 × 0.2 × 0.2 mm |
F(000) = 808 | |
Data collection top
KappaCCD diffractometer | Rint = 0 |
CCD rotation images, thick slices scans | θmax = 25.0°, θmin = 2.6° |
2866 measured reflections | h = −12→12 |
2851 independent reflections | k = −8→8 |
2608 reflections with I > 2σ(I) | l = −17→17 |
Refinement top
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0638P)2 + 0.7469P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.038 | (Δ/σ)max < 0.001 |
wR(F2) = 0.112 | Δρmax = 0.20 e Å−3 |
S = 1.10 | Δρmin = −0.21 e Å−3 |
2851 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
217 parameters | Absolute structure parameter: 0.33 (2) |
1 restraint | |
Crystal data top
C16H28N2O4S2 | Z = 4 |
Mr = 376.52 | Mo Kα radiation |
Tetragonal, P41 | µ = 0.27 mm−1 |
a = 11.3877 (4) Å | T = 293 K |
c = 15.9829 (6) Å | 0.5 × 0.2 × 0.2 mm |
V = 2072.66 (13) Å3 | |
Data collection top
KappaCCD diffractometer | 2608 reflections with I > 2σ(I) |
2866 measured reflections | Rint = 0 |
2851 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.038 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.112 | Δρmax = 0.20 e Å−3 |
S = 1.10 | Δρmin = −0.21 e Å−3 |
2851 reflections | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
217 parameters | Absolute structure parameter: 0.33 (2) |
1 restraint | |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C81 | 0.6516 (7) | 1.1643 (4) | 0.2957 (4) | 0.101 (2) | |
H812 | 0.6865 | 1.2369 | 0.278 | 0.151* | |
H818 | 0.7009 | 1.1278 | 0.3369 | 0.151* | |
H811 | 0.5757 | 1.1796 | 0.3195 | 0.151* | |
S1 | 0.90612 (9) | 0.70581 (9) | 0.12699 (6) | 0.0519 (3) | |
S11 | 0.92925 (8) | 0.92406 (9) | 0.34729 (5) | 0.0492 (3) | |
O31 | 0.5774 (2) | 0.7926 (2) | 0.41050 (16) | 0.0508 (7) | |
N11 | 0.7645 (3) | 0.8427 (3) | 0.24545 (17) | 0.0379 (7) | |
H11 | 0.7478 | 0.8092 | 0.1987 | 0.045* | |
O3 | 1.3029 (2) | 0.5792 (3) | 0.20480 (19) | 0.0597 (8) | |
C31 | 0.6000 (3) | 0.7814 (3) | 0.3295 (3) | 0.0444 (9) | |
N1 | 1.0701 (3) | 0.7891 (3) | 0.22841 (18) | 0.0398 (7) | |
H1 | 1.0876 | 0.8322 | 0.2708 | 0.048* | |
C21 | 0.6662 (3) | 0.8863 (3) | 0.2959 (2) | 0.0376 (8) | |
H21 | 0.6974 | 0.9316 | 0.343 | 0.045* | |
O2 | 1.1986 (3) | 0.6287 (3) | 0.3169 (2) | 0.0714 (9) | |
C2 | 1.1662 (3) | 0.7299 (3) | 0.1859 (2) | 0.0387 (8) | |
H2 | 1.1333 | 0.686 | 0.1387 | 0.046* | |
C5 | 1.2551 (3) | 0.8192 (3) | 0.1511 (2) | 0.0440 (9) | |
H52 | 1.28 | 0.8706 | 0.1961 | 0.053* | |
H51 | 1.3238 | 0.7772 | 0.1314 | 0.053* | |
C3 | 1.2223 (3) | 0.6426 (3) | 0.2454 (2) | 0.0464 (10) | |
C51 | 0.5843 (3) | 0.9654 (3) | 0.2445 (2) | 0.0427 (9) | |
H511 | 0.5621 | 0.9244 | 0.1937 | 0.051* | |
H512 | 0.5132 | 0.9796 | 0.2765 | 0.051* | |
C1 | 0.9586 (3) | 0.7824 (3) | 0.2074 (2) | 0.0339 (8) | |
C11 | 0.8761 (3) | 0.8506 (3) | 0.2658 (2) | 0.0339 (8) | |
O21 | 0.5715 (3) | 0.6990 (3) | 0.2882 (2) | 0.0799 (11) | |
C7 | 1.2952 (5) | 0.9884 (4) | 0.0564 (3) | 0.0710 (13) | |
H72 | 1.2646 | 1.0343 | 0.011 | 0.106* | |
H71 | 1.3677 | 0.9524 | 0.0396 | 0.106* | |
H73 | 1.309 | 1.0384 | 0.1038 | 0.106* | |
C6 | 1.2073 (3) | 0.8940 (4) | 0.0799 (2) | 0.0510 (10) | |
H6 | 1.1358 | 0.933 | 0.0998 | 0.061* | |
C61 | 0.6383 (3) | 1.0830 (3) | 0.2209 (3) | 0.0496 (10) | |
H61 | 0.7173 | 1.0673 | 0.1993 | 0.06* | |
C8 | 1.1745 (4) | 0.8202 (4) | 0.0027 (3) | 0.0656 (12) | |
H82 | 1.1188 | 0.7609 | 0.0185 | 0.098* | |
H83 | 1.2437 | 0.7835 | −0.0194 | 0.098* | |
H81 | 1.1403 | 0.8701 | −0.0391 | 0.098* | |
C71 | 0.5701 (5) | 1.1425 (5) | 0.1522 (3) | 0.0737 (14) | |
H712 | 0.6066 | 1.2162 | 0.1388 | 0.111* | |
H713 | 0.491 | 1.1561 | 0.1706 | 0.111* | |
H711 | 0.5694 | 1.0933 | 0.1035 | 0.111* | |
C4 | 1.3661 (4) | 0.4929 (4) | 0.2544 (4) | 0.0759 (14) | |
H42 | 1.4217 | 0.4526 | 0.2195 | 0.114* | |
H43 | 1.3116 | 0.4373 | 0.2773 | 0.114* | |
H41 | 1.4069 | 0.5318 | 0.2991 | 0.114* | |
C41 | 0.5110 (4) | 0.6977 (4) | 0.4482 (3) | 0.0691 (13) | |
H412 | 0.4989 | 0.714 | 0.5065 | 0.104* | |
H413 | 0.5537 | 0.6255 | 0.4423 | 0.104* | |
H411 | 0.4363 | 0.6908 | 0.4207 | 0.104* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C81 | 0.175 (7) | 0.049 (3) | 0.079 (4) | −0.004 (4) | −0.048 (4) | −0.005 (3) |
S1 | 0.0479 (6) | 0.0611 (6) | 0.0465 (6) | −0.0025 (5) | 0.0047 (4) | −0.0235 (5) |
S11 | 0.0454 (5) | 0.0609 (6) | 0.0414 (5) | −0.0009 (5) | 0.0025 (4) | −0.0188 (5) |
O31 | 0.0564 (16) | 0.0573 (17) | 0.0388 (15) | −0.0053 (13) | 0.0085 (12) | 0.0081 (12) |
N11 | 0.0418 (18) | 0.0458 (17) | 0.0259 (15) | −0.0037 (14) | 0.0085 (13) | −0.0086 (13) |
O3 | 0.0465 (15) | 0.0667 (18) | 0.0659 (19) | 0.0113 (14) | 0.0121 (14) | 0.0133 (16) |
C31 | 0.044 (2) | 0.039 (2) | 0.051 (3) | 0.0018 (17) | 0.0173 (17) | −0.0055 (19) |
N1 | 0.0423 (18) | 0.0480 (18) | 0.0293 (15) | −0.0032 (14) | 0.0070 (13) | −0.0062 (13) |
C21 | 0.041 (2) | 0.038 (2) | 0.034 (2) | −0.0025 (16) | 0.0074 (16) | −0.0065 (15) |
O2 | 0.113 (3) | 0.0548 (18) | 0.0457 (19) | 0.0131 (17) | 0.0172 (17) | 0.0103 (14) |
C2 | 0.0375 (19) | 0.050 (2) | 0.0283 (19) | 0.0012 (16) | 0.0075 (15) | −0.0028 (16) |
C5 | 0.041 (2) | 0.056 (2) | 0.035 (2) | 0.0026 (17) | 0.0089 (16) | 0.0018 (17) |
C3 | 0.053 (2) | 0.045 (2) | 0.042 (3) | −0.0050 (18) | 0.0026 (19) | −0.0045 (18) |
C51 | 0.038 (2) | 0.053 (2) | 0.036 (2) | −0.0045 (17) | 0.0055 (16) | −0.0075 (17) |
C1 | 0.040 (2) | 0.0345 (18) | 0.0273 (18) | −0.0036 (15) | 0.0061 (16) | −0.0008 (14) |
C11 | 0.042 (2) | 0.0318 (18) | 0.0284 (18) | −0.0062 (15) | 0.0080 (15) | 0.0016 (14) |
O21 | 0.100 (3) | 0.0601 (19) | 0.080 (2) | −0.0316 (19) | 0.050 (2) | −0.0273 (18) |
C7 | 0.081 (3) | 0.071 (3) | 0.061 (3) | −0.007 (3) | 0.013 (2) | 0.015 (2) |
C6 | 0.049 (2) | 0.061 (2) | 0.042 (2) | 0.007 (2) | 0.0158 (19) | 0.0112 (19) |
C61 | 0.045 (2) | 0.052 (2) | 0.052 (2) | −0.0018 (18) | −0.0027 (19) | 0.0079 (19) |
C8 | 0.073 (3) | 0.086 (3) | 0.038 (2) | −0.007 (3) | −0.003 (2) | 0.020 (2) |
C71 | 0.087 (3) | 0.070 (3) | 0.065 (3) | −0.001 (3) | −0.014 (3) | 0.015 (2) |
C4 | 0.059 (3) | 0.059 (3) | 0.110 (4) | 0.005 (2) | 0.001 (3) | 0.019 (3) |
C41 | 0.066 (3) | 0.072 (3) | 0.070 (3) | −0.003 (2) | 0.025 (3) | 0.027 (3) |
Geometric parameters (Å, º) top
C81—C61 | 1.520 (7) | C5—H51 | 0.97 |
C81—H812 | 0.96 | C51—C61 | 1.521 (6) |
C81—H818 | 0.96 | C51—H511 | 0.97 |
C81—H811 | 0.96 | C51—H512 | 0.97 |
S1—C1 | 1.665 (4) | C1—C11 | 1.535 (4) |
S11—C11 | 1.662 (4) | C7—C6 | 1.517 (6) |
O31—C31 | 1.326 (5) | C7—H72 | 0.96 |
O31—C41 | 1.450 (5) | C7—H71 | 0.96 |
N11—C11 | 1.315 (5) | C7—H73 | 0.96 |
N11—C21 | 1.466 (4) | C6—C8 | 1.538 (6) |
N11—H11 | 0.86 | C6—H6 | 0.98 |
O3—C3 | 1.335 (5) | C61—C71 | 1.506 (6) |
O3—C4 | 1.454 (6) | C61—H61 | 0.98 |
C31—O21 | 1.193 (5) | C8—H82 | 0.96 |
C31—C21 | 1.511 (5) | C8—H83 | 0.96 |
N1—C1 | 1.315 (5) | C8—H81 | 0.96 |
N1—C2 | 1.454 (5) | C71—H712 | 0.96 |
N1—H1 | 0.86 | C71—H713 | 0.96 |
C21—C51 | 1.535 (5) | C71—H711 | 0.96 |
C21—H21 | 0.98 | C4—H42 | 0.96 |
O2—C3 | 1.185 (5) | C4—H43 | 0.96 |
C2—C3 | 1.517 (6) | C4—H41 | 0.96 |
C2—C5 | 1.540 (5) | C41—H412 | 0.96 |
C2—H2 | 0.98 | C41—H413 | 0.96 |
C5—C6 | 1.522 (5) | C41—H411 | 0.96 |
C5—H52 | 0.97 | | |
| | | |
C61—C81—H812 | 109.5 | C11—C1—S1 | 121.0 (2) |
C61—C81—H818 | 109.5 | N11—C11—C1 | 114.0 (3) |
H812—C81—H818 | 109.5 | N11—C11—S11 | 125.4 (3) |
C61—C81—H811 | 109.5 | C1—C11—S11 | 120.5 (2) |
H812—C81—H811 | 109.5 | C6—C7—H72 | 109.5 |
H818—C81—H811 | 109.5 | C6—C7—H71 | 109.5 |
C31—O31—C41 | 115.8 (3) | H72—C7—H71 | 109.5 |
C11—N11—C21 | 125.4 (3) | C6—C7—H73 | 109.5 |
C11—N11—H11 | 117.3 | H72—C7—H73 | 109.5 |
C21—N11—H11 | 117.3 | H71—C7—H73 | 109.5 |
C3—O3—C4 | 116.2 (4) | C7—C6—C5 | 110.2 (4) |
O21—C31—O31 | 124.3 (4) | C7—C6—C8 | 110.5 (4) |
O21—C31—C21 | 124.1 (4) | C5—C6—C8 | 112.4 (3) |
O31—C31—C21 | 111.6 (3) | C7—C6—H6 | 107.9 |
C1—N1—C2 | 125.5 (3) | C5—C6—H6 | 107.9 |
C1—N1—H1 | 117.3 | C8—C6—H6 | 107.9 |
C2—N1—H1 | 117.3 | C71—C61—C81 | 110.5 (4) |
N11—C21—C31 | 108.0 (3) | C71—C61—C51 | 111.6 (3) |
N11—C21—C51 | 111.7 (3) | C81—C61—C51 | 112.4 (4) |
C31—C21—C51 | 110.6 (3) | C71—C61—H61 | 107.3 |
N11—C21—H21 | 108.9 | C81—C61—H61 | 107.3 |
C31—C21—H21 | 108.9 | C51—C61—H61 | 107.3 |
C51—C21—H21 | 108.9 | C6—C8—H82 | 109.5 |
N1—C2—C3 | 109.2 (3) | C6—C8—H83 | 109.5 |
N1—C2—C5 | 110.9 (3) | H82—C8—H83 | 109.5 |
C3—C2—C5 | 112.5 (3) | C6—C8—H81 | 109.5 |
N1—C2—H2 | 108 | H82—C8—H81 | 109.5 |
C3—C2—H2 | 108 | H83—C8—H81 | 109.5 |
C5—C2—H2 | 108 | C61—C71—H712 | 109.5 |
C6—C5—C2 | 113.8 (3) | C61—C71—H713 | 109.5 |
C6—C5—H52 | 108.8 | H712—C71—H713 | 109.5 |
C2—C5—H52 | 108.8 | C61—C71—H711 | 109.5 |
C6—C5—H51 | 108.8 | H712—C71—H711 | 109.5 |
C2—C5—H51 | 108.8 | H713—C71—H711 | 109.5 |
H52—C5—H51 | 107.7 | O3—C4—H42 | 109.5 |
O2—C3—O3 | 123.6 (4) | O3—C4—H43 | 109.5 |
O2—C3—C2 | 126.6 (4) | H42—C4—H43 | 109.5 |
O3—C3—C2 | 109.8 (3) | O3—C4—H41 | 109.5 |
C61—C51—C21 | 113.8 (3) | H42—C4—H41 | 109.5 |
C61—C51—H511 | 108.8 | H43—C4—H41 | 109.5 |
C21—C51—H511 | 108.8 | O31—C41—H412 | 109.5 |
C61—C51—H512 | 108.8 | O31—C41—H413 | 109.5 |
C21—C51—H512 | 108.8 | H412—C41—H413 | 109.5 |
H511—C51—H512 | 107.7 | O31—C41—H411 | 109.5 |
N1—C1—C11 | 114.0 (3) | H412—C41—H411 | 109.5 |
N1—C1—S1 | 125.0 (3) | H413—C41—H411 | 109.5 |
| | | |
C41—O31—C31—O21 | −1.5 (6) | N1—C1—C11—N11 | −179.2 (3) |
C41—O31—C31—C21 | 178.3 (3) | S1—C1—C11—N11 | −0.6 (4) |
O21—C31—C21—N11 | −47.1 (5) | N1—C1—C11—S11 | −0.2 (4) |
O21—C31—C21—C51 | 75.3 (5) | S1—C1—C11—S11 | 178.5 (2) |
O31—C31—C21—C51 | −104.5 (4) | C2—C5—C6—C7 | 173.4 (3) |
C1—N1—C2—C5 | 119.4 (4) | C2—C5—C6—C8 | −62.9 (4) |
C3—C2—C5—C6 | 169.6 (3) | C21—C51—C61—C71 | 164.3 (3) |
C4—O3—C3—O2 | −2.5 (6) | C21—C51—C61—C81 | −70.9 (5) |
C4—O3—C3—C2 | 178.8 (3) | C11—N11—C21—C51 | 128.0 (4) |
N1—C2—C3—O2 | −4.8 (5) | C11—C1—N1—C2 | 177.8 (3) |
C5—C2—C3—O2 | 118.9 (4) | C1—N1—C2—C3 | −116.0 (4) |
C5—C2—C3—O3 | −62.5 (4) | N1—C2—C3—O3 | 173.8 (3) |
C31—C21—C51—C61 | 170.1 (3) | N1—C2—C5—C6 | −67.7 (4) |
C2—N1—C1—C11 | 177.7 (3) | C1—C11—N11—C21 | 171.9 (3) |
C2—N1—C1—S1 | −0.9 (5) | C11—N11—C21—C31 | −110.3 (4) |
C21—N11—C11—C1 | 171.9 (3) | N11—C21—C31—O31 | 133.1 (3) |
C21—N11—C11—S11 | −7.1 (5) | N11—C21—C51—C61 | −69.7 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H11···O2i | 0.86 | 2.51 | 3.280 (4) | 150 |
N1—H1···S1ii | 0.86 | 3.02 | 3.732 (3) | 142 |
N11—H11···S1 | 0.86 | 2.44 | 2.935 (3) | 117 |
N1—H1···S11 | 0.86 | 2.42 | 2.923 (3) | 118 |
Symmetry codes: (i) y, −x+2, z−1/4; (ii) −y+2, x, z+1/4. |
Experimental details
| (I) | (II) |
Crystal data |
Chemical formula | C16H28N2O5S | C16H28N2O4S2 |
Mr | 360.46 | 376.52 |
Crystal system, space group | Orthorhombic, P212121 | Tetragonal, P41 |
Temperature (K) | 293 | 293 |
a, b, c (Å) | 12.562 (9), 16.156 (5), 21.086 (8) | 11.3877 (4), 11.3877 (4), 15.9829 (6) |
α, β, γ (°) | 90, 90.000 (3), 90 | 90, 90, 90 |
V (Å3) | 4279 (4) | 2072.66 (13) |
Z | 8 | 4 |
Radiation type | Cu Kα | Mo Kα |
µ (mm−1) | 1.55 | 0.27 |
Crystal size (mm) | 0.4 × 0.2 × 0.15 | 0.5 × 0.2 × 0.2 |
|
Data collection |
Diffractometer | Enraf Nonius CAD4 diffractometer | KappaCCD diffractometer |
Absorption correction | ψ scan North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
Number of ψ scan sets used was 7
Theta correction was applied.
Averaged transmission function was used.
No Fourier smoothing was applied. | – |
Tmin, Tmax | 0.752, 0.791 | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9699, 8972, 4033 | 2866, 2851, 2608 |
Rint | 0.035 | 0 |
(sin θ/λ)max (Å−1) | 0.631 | 0.594 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.060, 0.174, 1.01 | 0.038, 0.112, 1.10 |
No. of reflections | 8972 | 2851 |
No. of parameters | 433 | 217 |
No. of restraints | 0 | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.24, −0.16 | 0.20, −0.21 |
Absolute structure | Flack H D (1983), Acta Cryst. A39, 876-881 | Flack H D (1983), Acta Cryst. A39, 876-881 |
Absolute structure parameter | −0.01 (3) | 0.33 (2) |
Hydrogen-bond geometry (Å, º) for (I) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O12 | 0.86 | 2.38 | 3.135 (5) | 146.1 |
N1—H1···S11 | 0.86 | 2.58 | 3.009 (4) | 111.9 |
N11—H11···O22i | 0.86 | 2.22 | 3.021 (5) | 155.1 |
N12—H12···O1ii | 0.86 | 2.36 | 3.105 (5) | 144.7 |
N12—H12···S13 | 0.86 | 2.54 | 2.993 (4) | 114 |
N13—H13···O2 | 0.86 | 2.37 | 3.155 (6) | 151.8 |
N11—H11···O1 | 0.86 | 2.23 | 2.636 (5) | 109 |
N13—H13···O12 | 0.86 | 2.22 | 2.634 (5) | 109 |
Symmetry codes: (i) −x+2, y+1/2, −z+1/2; (ii) −x+2, y−1/2, −z+1/2. |
Selected torsion angles (º) for (II) topC11—C1—N1—C2 | 177.8 (3) | C1—C11—N11—C21 | 171.9 (3) |
C1—N1—C2—C3 | −116.0 (4) | C11—N11—C21—C31 | −110.3 (4) |
N1—C2—C3—O3 | 173.8 (3) | N11—C21—C31—O31 | 133.1 (3) |
N1—C2—C5—C6 | −67.7 (4) | N11—C21—C51—C61 | −69.7 (4) |
Hydrogen-bond geometry (Å, º) for (II) top
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H11···O2i | 0.86 | 2.51 | 3.280 (4) | 149.9 |
N1—H1···S1ii | 0.86 | 3.02 | 3.732 (3) | 141.5 |
N11—H11···S1 | 0.86 | 2.44 | 2.935 (3) | 117.3 |
N1—H1···S11 | 0.86 | 2.42 | 2.923 (3) | 118.2 |
Symmetry codes: (i) y, −x+2, z−1/4; (ii) −y+2, x, z+1/4. |