Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536800018961/na6015sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536800018961/na6015Isup2.hkl |
CCDC reference: 155884
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.003 Å
- R factor = 0.039
- wR factor = 0.077
- Data-to-parameter ratio = 14.4
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.50 From the CIF: _reflns_number_total 4345 Count of symmetry unique reflns 2906 Completeness (_total/calc) 149.52% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1439 Fraction of Friedel pairs measured 0.495 Are heavy atom types Z>Si present yes WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure
The title compound was prepared by reacting Nε-benzyloxycarbonyl-L-lysine with chlorotrimethylsylane (1.85 equivalents), diisopropylethylamine (2.3 equivalents) and ortho-nitrobenzenesulfonyl chloride (0.9 equivalents) in anhydrous dichloromethane under argon over 12 h (273 K to reflux), followed by aqueous work-up and extraction. The amino acid derivative was recrystalized by dissolving the crude material in a hot ethanol solution, followed by slow cooling to room temperature.
H atoms on C atoms were placed in calculated positions with C—H bond distances in the range 0.95–1.00 Å and Uiso = 1.2Ueq of the attached atom, and thereafter treated as riding. H atoms on O and N atoms were placed by difference maps and refined individually. The absolute configuration was determined by refinement of the Flack (1983) parameter, and corresponds with that of L-lysine.
Data collection: COLLECT (Nonius 2000); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: direct methods using SIR (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
Fig. 1. The atom-numbering scheme for (I) with displacement ellipsoids at the 50% probability level. |
C20H23N3O8S | Dx = 1.422 Mg m−3 |
Mr = 465.47 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P21212 | Cell parameters from 13981 reflections |
a = 11.7629 (2) Å | θ = 2.5–27.5° |
b = 34.5731 (6) Å | µ = 0.20 mm−1 |
c = 5.3477 (2) Å | T = 120 K |
V = 2174.8 (2) Å3 | Fragment, colorless |
Z = 4 | 0.23 × 0.12 × 0.10 mm |
F(000) = 976 |
KappaCCD (with Oxford Cryostream) diffractometer | 4345 independent reflections |
Radiation source: fine-focus sealed tube | 3563 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.050 |
ω scans with κ offsets | θmax = 27.5°, θmin = 3.4° |
Absorption correction: multi-scan (HKL SCALEPACK; Otwinowski & Minor, 1997) | h = −15→15 |
Tmin = 0.937, Tmax = 0.980 | k = −44→44 |
13981 measured reflections | l = −5→5 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.039 | w = 1/[σ2(Fo2) + (0.0239P)2 + 0.7661P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.077 | (Δ/σ)max = 0.001 |
S = 1.05 | Δρmax = 0.21 e Å−3 |
4345 reflections | Δρmin = −0.24 e Å−3 |
302 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0039 (6) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983); 1439 Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: −0.07 (7) |
C20H23N3O8S | V = 2174.8 (2) Å3 |
Mr = 465.47 | Z = 4 |
Orthorhombic, P21212 | Mo Kα radiation |
a = 11.7629 (2) Å | µ = 0.20 mm−1 |
b = 34.5731 (6) Å | T = 120 K |
c = 5.3477 (2) Å | 0.23 × 0.12 × 0.10 mm |
KappaCCD (with Oxford Cryostream) diffractometer | 4345 independent reflections |
Absorption correction: multi-scan (HKL SCALEPACK; Otwinowski & Minor, 1997) | 3563 reflections with I > 2σ(I) |
Tmin = 0.937, Tmax = 0.980 | Rint = 0.050 |
13981 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.077 | Δρmax = 0.21 e Å−3 |
S = 1.05 | Δρmin = −0.24 e Å−3 |
4345 reflections | Absolute structure: Flack (1983); 1439 Friedel pairs |
302 parameters | Absolute structure parameter: −0.07 (7) |
0 restraints |
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. |
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 > σ(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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.43876 (4) | 0.677475 (15) | 0.47852 (10) | 0.02199 (14) | |
O1 | 0.44420 (14) | 0.68264 (4) | 0.7440 (3) | 0.0298 (4) | |
O2 | 0.53146 (12) | 0.69058 (4) | 0.3276 (3) | 0.0273 (4) | |
O3 | 0.26251 (14) | 0.58376 (5) | 0.2702 (3) | 0.0360 (4) | |
O4 | 0.34781 (14) | 0.57133 (5) | −0.0963 (3) | 0.0345 (4) | |
H40 | 0.290 (2) | 0.5532 (9) | −0.110 (6) | 0.060 (9)* | |
O5 | 0.82527 (14) | 0.47725 (4) | 0.8337 (3) | 0.0304 (4) | |
O6 | 0.95282 (12) | 0.45492 (4) | 0.5520 (3) | 0.0294 (4) | |
O7 | 0.09305 (15) | 0.68765 (6) | 0.8123 (4) | 0.0580 (6) | |
O8 | 0.22750 (15) | 0.64804 (5) | 0.7149 (3) | 0.0424 (5) | |
N1 | 0.42408 (17) | 0.63207 (5) | 0.4233 (3) | 0.0230 (4) | |
H1N | 0.371 (2) | 0.6243 (7) | 0.501 (5) | 0.040 (8)* | |
N2 | 0.81842 (16) | 0.49541 (5) | 0.4267 (4) | 0.0269 (5) | |
H2N | 0.839 (2) | 0.4895 (7) | 0.276 (5) | 0.032 (7)* | |
N3 | 0.17488 (17) | 0.67823 (6) | 0.6835 (4) | 0.0363 (5) | |
C1 | 0.43581 (19) | 0.61725 (6) | 0.1663 (4) | 0.0220 (5) | |
H1 | 0.4274 | 0.6394 | 0.0475 | 0.026* | |
C2 | 0.3387 (2) | 0.58930 (6) | 0.1230 (5) | 0.0261 (5) | |
C3 | 0.55223 (18) | 0.59877 (6) | 0.1248 (4) | 0.0241 (5) | |
H3A | 0.5581 | 0.5902 | −0.0514 | 0.029* | |
H3B | 0.6119 | 0.6185 | 0.1538 | 0.029* | |
C4 | 0.57374 (19) | 0.56441 (6) | 0.2952 (4) | 0.0275 (5) | |
H4A | 0.5652 | 0.5729 | 0.4710 | 0.033* | |
H4B | 0.5152 | 0.5445 | 0.2623 | 0.033* | |
C5 | 0.69042 (19) | 0.54635 (6) | 0.2627 (4) | 0.0256 (5) | |
H5A | 0.6970 | 0.5352 | 0.0927 | 0.031* | |
H5B | 0.7496 | 0.5665 | 0.2815 | 0.031* | |
C6 | 0.70880 (18) | 0.51500 (7) | 0.4550 (5) | 0.0290 (6) | |
H6A | 0.7045 | 0.5265 | 0.6242 | 0.035* | |
H6B | 0.6470 | 0.4957 | 0.4404 | 0.035* | |
C7 | 0.86202 (18) | 0.47584 (6) | 0.6171 (5) | 0.0254 (5) | |
C8 | 0.31738 (19) | 0.70416 (6) | 0.3731 (4) | 0.0249 (5) | |
C9 | 0.20813 (18) | 0.70432 (7) | 0.4782 (5) | 0.0295 (5) | |
C10 | 0.1252 (2) | 0.72941 (8) | 0.3929 (6) | 0.0447 (7) | |
H10 | 0.0516 | 0.7291 | 0.4659 | 0.054* | |
C11 | 0.1496 (3) | 0.75489 (8) | 0.2017 (6) | 0.0537 (8) | |
H11 | 0.0929 | 0.7723 | 0.1435 | 0.064* | |
C12 | 0.2561 (3) | 0.75510 (8) | 0.0954 (5) | 0.0492 (7) | |
H12 | 0.2725 | 0.7723 | −0.0382 | 0.059* | |
C13 | 0.3390 (2) | 0.73034 (6) | 0.1824 (4) | 0.0341 (6) | |
H13 | 0.4127 | 0.7312 | 0.1100 | 0.041* | |
C14 | 0.9993 (2) | 0.43026 (7) | 0.7471 (5) | 0.0330 (6) | |
H14A | 0.9370 | 0.4185 | 0.8453 | 0.040* | |
H14B | 1.0474 | 0.4457 | 0.8618 | 0.040* | |
C15 | 1.06902 (18) | 0.39928 (6) | 0.6233 (4) | 0.0256 (5) | |
C16 | 1.17252 (19) | 0.38867 (6) | 0.7264 (4) | 0.0281 (5) | |
H16 | 1.2004 | 0.4021 | 0.8689 | 0.034* | |
C17 | 1.2359 (2) | 0.35880 (7) | 0.6246 (5) | 0.0317 (6) | |
H17 | 1.3061 | 0.3515 | 0.6988 | 0.038* | |
C18 | 1.1968 (2) | 0.33967 (7) | 0.4152 (5) | 0.0350 (6) | |
H18 | 1.2406 | 0.3194 | 0.3435 | 0.042* | |
C19 | 1.0939 (2) | 0.34998 (7) | 0.3097 (4) | 0.0340 (6) | |
H19 | 1.0668 | 0.3366 | 0.1665 | 0.041* | |
C20 | 1.03010 (18) | 0.37977 (7) | 0.4121 (4) | 0.0293 (6) | |
H20 | 0.9597 | 0.3869 | 0.3380 | 0.035* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0248 (3) | 0.0211 (3) | 0.0201 (3) | 0.0001 (2) | −0.0005 (2) | 0.0015 (2) |
O1 | 0.0403 (9) | 0.0300 (9) | 0.0193 (8) | −0.0023 (8) | −0.0030 (8) | −0.0006 (7) |
O2 | 0.0258 (8) | 0.0265 (8) | 0.0296 (9) | −0.0019 (7) | 0.0020 (7) | 0.0024 (7) |
O3 | 0.0341 (9) | 0.0370 (10) | 0.0368 (10) | −0.0086 (8) | 0.0043 (9) | −0.0038 (8) |
O4 | 0.0327 (9) | 0.0404 (10) | 0.0303 (10) | −0.0036 (8) | −0.0036 (8) | −0.0103 (8) |
O5 | 0.0320 (9) | 0.0307 (9) | 0.0285 (10) | 0.0056 (7) | 0.0067 (8) | 0.0034 (7) |
O6 | 0.0250 (8) | 0.0324 (8) | 0.0308 (9) | 0.0086 (7) | 0.0055 (8) | 0.0068 (7) |
O7 | 0.0385 (11) | 0.0708 (14) | 0.0648 (14) | −0.0056 (10) | 0.0281 (10) | −0.0226 (11) |
O8 | 0.0453 (11) | 0.0405 (11) | 0.0414 (11) | −0.0045 (9) | 0.0156 (9) | 0.0007 (9) |
N1 | 0.0261 (10) | 0.0238 (10) | 0.0191 (10) | 0.0010 (9) | 0.0029 (9) | 0.0030 (8) |
N2 | 0.0253 (10) | 0.0286 (11) | 0.0267 (13) | 0.0064 (9) | 0.0037 (9) | 0.0042 (10) |
N3 | 0.0274 (11) | 0.0430 (13) | 0.0386 (13) | −0.0059 (11) | 0.0075 (10) | −0.0188 (11) |
C1 | 0.0287 (12) | 0.0202 (11) | 0.0171 (12) | 0.0034 (10) | −0.0002 (10) | 0.0018 (9) |
C2 | 0.0269 (12) | 0.0248 (12) | 0.0267 (13) | 0.0054 (10) | −0.0044 (11) | 0.0000 (11) |
C3 | 0.0245 (11) | 0.0280 (12) | 0.0199 (11) | −0.0005 (10) | 0.0031 (11) | −0.0001 (10) |
C4 | 0.0276 (12) | 0.0282 (12) | 0.0267 (12) | 0.0039 (10) | 0.0006 (11) | 0.0025 (10) |
C5 | 0.0266 (12) | 0.0278 (12) | 0.0225 (12) | 0.0055 (10) | 0.0020 (10) | −0.0011 (11) |
C6 | 0.0225 (11) | 0.0288 (12) | 0.0358 (15) | 0.0055 (10) | 0.0028 (10) | 0.0062 (12) |
C7 | 0.0211 (11) | 0.0202 (12) | 0.0349 (15) | −0.0030 (9) | 0.0048 (11) | 0.0008 (11) |
C8 | 0.0319 (13) | 0.0226 (11) | 0.0204 (12) | 0.0041 (10) | −0.0015 (11) | −0.0056 (10) |
C9 | 0.0296 (12) | 0.0295 (12) | 0.0296 (13) | 0.0029 (10) | −0.0013 (11) | −0.0105 (11) |
C10 | 0.0293 (14) | 0.0488 (16) | 0.0560 (19) | 0.0134 (13) | −0.0055 (13) | −0.0257 (16) |
C11 | 0.063 (2) | 0.0445 (17) | 0.054 (2) | 0.0306 (15) | −0.0231 (16) | −0.0134 (15) |
C12 | 0.077 (2) | 0.0320 (14) | 0.0390 (16) | 0.0223 (15) | −0.0072 (15) | 0.0022 (12) |
C13 | 0.0493 (16) | 0.0245 (12) | 0.0285 (14) | 0.0098 (12) | −0.0005 (12) | −0.0029 (11) |
C14 | 0.0351 (13) | 0.0346 (14) | 0.0293 (14) | 0.0118 (11) | 0.0010 (11) | 0.0052 (12) |
C15 | 0.0239 (12) | 0.0258 (11) | 0.0270 (12) | −0.0011 (10) | 0.0039 (11) | 0.0055 (10) |
C16 | 0.0278 (13) | 0.0291 (12) | 0.0274 (13) | 0.0016 (11) | −0.0027 (11) | −0.0017 (11) |
C17 | 0.0282 (12) | 0.0345 (13) | 0.0323 (13) | 0.0088 (11) | −0.0032 (11) | −0.0030 (12) |
C18 | 0.0340 (13) | 0.0319 (13) | 0.0392 (15) | 0.0044 (11) | 0.0031 (12) | −0.0075 (12) |
C19 | 0.0368 (14) | 0.0359 (14) | 0.0293 (14) | −0.0055 (11) | −0.0010 (11) | −0.0054 (11) |
C20 | 0.0229 (12) | 0.0342 (13) | 0.0308 (13) | 0.0009 (10) | −0.0022 (11) | 0.0060 (11) |
S1—O2 | 1.4301 (15) | C5—H5A | 0.99 |
S1—O1 | 1.4323 (15) | C5—H5B | 0.99 |
S1—N1 | 1.6065 (18) | C6—H6A | 0.99 |
S1—C8 | 1.791 (2) | C6—H6B | 0.99 |
O3—C2 | 1.207 (3) | C8—C13 | 1.387 (3) |
O4—C2 | 1.331 (3) | C8—C9 | 1.403 (3) |
O4—H40 | 0.93 (3) | C9—C10 | 1.383 (3) |
O5—C7 | 1.238 (3) | C10—C11 | 1.380 (4) |
O6—C7 | 1.336 (3) | C10—H10 | 0.95 |
O6—C14 | 1.454 (3) | C11—C12 | 1.376 (4) |
O7—N3 | 1.228 (3) | C11—H11 | 0.95 |
O8—N3 | 1.225 (3) | C12—C13 | 1.379 (4) |
N1—C1 | 1.473 (3) | C12—H12 | 0.95 |
N1—H1N | 0.80 (3) | C13—H13 | 0.95 |
N2—C7 | 1.326 (3) | C14—C15 | 1.503 (3) |
N2—C6 | 1.464 (3) | C14—H14A | 0.99 |
N2—H2N | 0.87 (2) | C14—H14B | 0.99 |
N3—C9 | 1.474 (3) | C15—C16 | 1.386 (3) |
C1—C2 | 1.514 (3) | C15—C20 | 1.393 (3) |
C1—C3 | 1.527 (3) | C16—C17 | 1.385 (3) |
C1—H1 | 1.00 | C16—H16 | 0.95 |
C3—C4 | 1.519 (3) | C17—C18 | 1.380 (3) |
C3—H3A | 0.99 | C17—H17 | 0.95 |
C3—H3B | 0.99 | C18—C19 | 1.382 (3) |
C4—C5 | 1.518 (3) | C18—H18 | 0.95 |
C4—H4A | 0.99 | C19—C20 | 1.387 (3) |
C4—H4B | 0.99 | C19—H19 | 0.95 |
C5—C6 | 1.509 (3) | C20—H20 | 0.95 |
O2—S1—O1 | 119.06 (10) | C5—C6—H6B | 109.0 |
O2—S1—N1 | 106.72 (10) | H6A—C6—H6B | 107.8 |
O1—S1—N1 | 107.98 (9) | O5—C7—N2 | 124.3 (2) |
O2—S1—C8 | 105.49 (10) | O5—C7—O6 | 123.0 (2) |
O1—S1—C8 | 106.47 (10) | N2—C7—O6 | 112.7 (2) |
N1—S1—C8 | 111.09 (10) | C13—C8—C9 | 117.4 (2) |
C2—O4—H40 | 109.0 (18) | C13—C8—S1 | 114.92 (18) |
C7—O6—C14 | 115.53 (17) | C9—C8—S1 | 127.33 (18) |
C1—N1—S1 | 120.09 (15) | C10—C9—C8 | 121.1 (2) |
C1—N1—H1N | 116.2 (19) | C10—C9—N3 | 116.3 (2) |
S1—N1—H1N | 108.4 (18) | C8—C9—N3 | 122.6 (2) |
C7—N2—C6 | 119.8 (2) | C11—C10—C9 | 119.9 (3) |
C7—N2—H2N | 119.2 (16) | C11—C10—H10 | 120.1 |
C6—N2—H2N | 116.7 (17) | C9—C10—H10 | 120.1 |
O8—N3—O7 | 123.0 (2) | C12—C11—C10 | 119.9 (3) |
O8—N3—C9 | 119.32 (19) | C12—C11—H11 | 120.0 |
O7—N3—C9 | 117.6 (2) | C10—C11—H11 | 120.0 |
N1—C1—C2 | 107.09 (18) | C11—C12—C13 | 120.1 (3) |
N1—C1—C3 | 111.42 (17) | C11—C12—H12 | 119.9 |
C2—C1—C3 | 112.79 (17) | C13—C12—H12 | 119.9 |
N1—C1—H1 | 108.5 | C12—C13—C8 | 121.6 (3) |
C2—C1—H1 | 108.5 | C12—C13—H13 | 119.2 |
C3—C1—H1 | 108.5 | C8—C13—H13 | 119.2 |
O3—C2—O4 | 124.1 (2) | O6—C14—C15 | 107.89 (19) |
O3—C2—C1 | 124.1 (2) | O6—C14—H14A | 110.1 |
O4—C2—C1 | 111.8 (2) | C15—C14—H14A | 110.1 |
C4—C3—C1 | 112.91 (17) | O6—C14—H14B | 110.1 |
C4—C3—H3A | 109.0 | C15—C14—H14B | 110.1 |
C1—C3—H3A | 109.0 | H14A—C14—H14B | 108.4 |
C4—C3—H3B | 109.0 | C16—C15—C20 | 118.9 (2) |
C1—C3—H3B | 109.0 | C16—C15—C14 | 119.5 (2) |
H3A—C3—H3B | 107.8 | C20—C15—C14 | 121.5 (2) |
C5—C4—C3 | 113.82 (18) | C17—C16—C15 | 120.9 (2) |
C5—C4—H4A | 108.8 | C17—C16—H16 | 119.5 |
C3—C4—H4A | 108.8 | C15—C16—H16 | 119.5 |
C5—C4—H4B | 108.8 | C18—C17—C16 | 119.8 (2) |
C3—C4—H4B | 108.8 | C18—C17—H17 | 120.1 |
H4A—C4—H4B | 107.7 | C16—C17—H17 | 120.1 |
C6—C5—C4 | 110.31 (18) | C17—C18—C19 | 120.0 (2) |
C6—C5—H5A | 109.6 | C17—C18—H18 | 120.0 |
C4—C5—H5A | 109.6 | C19—C18—H18 | 120.0 |
C6—C5—H5B | 109.6 | C18—C19—C20 | 120.3 (2) |
C4—C5—H5B | 109.6 | C18—C19—H19 | 119.9 |
H5A—C5—H5B | 108.1 | C20—C19—H19 | 119.9 |
N2—C6—C5 | 112.82 (19) | C19—C20—C15 | 120.1 (2) |
N2—C6—H6A | 109.0 | C19—C20—H20 | 119.9 |
C5—C6—H6A | 109.0 | C15—C20—H20 | 119.9 |
N2—C6—H6B | 109.0 | ||
O2—S1—N1—C1 | −40.33 (19) | S1—C8—C9—C10 | 173.24 (19) |
O1—S1—N1—C1 | −169.43 (16) | C13—C8—C9—N3 | −179.4 (2) |
C8—S1—N1—C1 | 74.18 (19) | S1—C8—C9—N3 | −6.7 (3) |
S1—N1—C1—C2 | −135.06 (16) | O8—N3—C9—C10 | 157.0 (2) |
S1—N1—C1—C3 | 101.17 (18) | O7—N3—C9—C10 | −21.4 (3) |
N1—C1—C2—O3 | 5.7 (3) | O8—N3—C9—C8 | −23.1 (3) |
C3—C1—C2—O3 | 128.6 (2) | O7—N3—C9—C8 | 158.5 (2) |
N1—C1—C2—O4 | −173.85 (17) | C8—C9—C10—C11 | −0.2 (4) |
C3—C1—C2—O4 | −50.9 (2) | N3—C9—C10—C11 | 179.8 (2) |
N1—C1—C3—C4 | 61.1 (2) | C9—C10—C11—C12 | 0.4 (4) |
C2—C1—C3—C4 | −59.4 (2) | C10—C11—C12—C13 | −1.1 (4) |
C1—C3—C4—C5 | −178.21 (18) | C11—C12—C13—C8 | 1.5 (4) |
C3—C4—C5—C6 | 174.65 (19) | C9—C8—C13—C12 | −1.3 (3) |
C7—N2—C6—C5 | 160.1 (2) | S1—C8—C13—C12 | −174.8 (2) |
C4—C5—C6—N2 | 177.72 (19) | C7—O6—C14—C15 | 159.54 (18) |
C6—N2—C7—O5 | −11.2 (3) | O6—C14—C15—C16 | 138.4 (2) |
C6—N2—C7—O6 | 170.50 (18) | O6—C14—C15—C20 | −44.1 (3) |
C14—O6—C7—O5 | 6.5 (3) | C20—C15—C16—C17 | −1.0 (3) |
C14—O6—C7—N2 | −175.15 (19) | C14—C15—C16—C17 | 176.5 (2) |
O2—S1—C8—C13 | −0.69 (19) | C15—C16—C17—C18 | 1.1 (4) |
O1—S1—C8—C13 | 126.71 (17) | C16—C17—C18—C19 | −0.9 (4) |
N1—S1—C8—C13 | −115.97 (18) | C17—C18—C19—C20 | 0.6 (4) |
O2—S1—C8—C9 | −173.5 (2) | C18—C19—C20—C15 | −0.5 (4) |
O1—S1—C8—C9 | −46.1 (2) | C16—C15—C20—C19 | 0.7 (3) |
N1—S1—C8—C9 | 71.2 (2) | C14—C15—C20—C19 | −176.7 (2) |
C13—C8—C9—C10 | 0.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H40···O5i | 0.93 (3) | 1.75 (3) | 2.666 (2) | 172 (3) |
N1—H1N···O3 | 0.80 (3) | 2.26 (3) | 2.659 (3) | 111 (2) |
N1—H1N···O8 | 0.80 (3) | 2.19 (3) | 2.843 (3) | 138 (2) |
N2—H2N···O5ii | 0.87 (2) | 2.41 (3) | 3.233 (3) | 160 (2) |
C1—H1···O1ii | 1.00 | 2.22 | 3.197 (3) | 167 |
C11—H11···O1iii | 0.95 | 2.42 | 3.254 (4) | 146 |
Symmetry codes: (i) −x+1, −y+1, z−1; (ii) x, y, z−1; (iii) x−1/2, −y+3/2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C20H23N3O8S |
Mr | 465.47 |
Crystal system, space group | Orthorhombic, P21212 |
Temperature (K) | 120 |
a, b, c (Å) | 11.7629 (2), 34.5731 (6), 5.3477 (2) |
V (Å3) | 2174.8 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.20 |
Crystal size (mm) | 0.23 × 0.12 × 0.10 |
Data collection | |
Diffractometer | KappaCCD (with Oxford Cryostream) diffractometer |
Absorption correction | Multi-scan (HKL SCALEPACK; Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.937, 0.980 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13981, 4345, 3563 |
Rint | 0.050 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.077, 1.05 |
No. of reflections | 4345 |
No. of parameters | 302 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.21, −0.24 |
Absolute structure | Flack (1983); 1439 Friedel pairs |
Absolute structure parameter | −0.07 (7) |
Computer programs: COLLECT (Nonius 2000), DENZO and SCALEPACK (Otwinowski & Minor, 1997), direct methods using SIR (Altomare et al., 1993), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXL97.
S1—O2 | 1.4301 (15) | O5—C7 | 1.238 (3) |
S1—O1 | 1.4323 (15) | O6—C7 | 1.336 (3) |
S1—N1 | 1.6065 (18) | N1—C1 | 1.473 (3) |
S1—C8 | 1.791 (2) | N2—C7 | 1.326 (3) |
O3—C2 | 1.207 (3) | N2—C6 | 1.464 (3) |
O4—C2 | 1.331 (3) | ||
S1—N1—C1—C3 | 101.17 (18) | O8—N3—C9—C8 | −23.1 (3) |
N1—C1—C2—O3 | 5.7 (3) | O6—C14—C15—C20 | −44.1 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H40···O5i | 0.93 (3) | 1.75 (3) | 2.666 (2) | 172 (3) |
N1—H1N···O3 | 0.80 (3) | 2.26 (3) | 2.659 (3) | 111 (2) |
N1—H1N···O8 | 0.80 (3) | 2.19 (3) | 2.843 (3) | 138 (2) |
N2—H2N···O5ii | 0.87 (2) | 2.41 (3) | 3.233 (3) | 160 (2) |
C1—H1···O1ii | 1.00 | 2.22 | 3.197 (3) | 167 |
C11—H11···O1iii | 0.95 | 2.42 | 3.254 (4) | 146 |
Symmetry codes: (i) −x+1, −y+1, z−1; (ii) x, y, z−1; (iii) x−1/2, −y+3/2, −z+1. |
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The solid-phase peptide synthesis by the use of Nα-protecting groups such as Fmoc (9-fluorenylmethoxycarbonyl) is widely used as described by Wenschuh et al. (1994). In an effort to increase the yield of the amino acid coupling reaction, the title compound, (I), was synthesized. The 2-nitrobenzenesulfonyl protecting group is smaller than the Fmoc group and is expected to increase the amino acid coupling yield due to decreased steric interactions with the nucleophile. The crystal structure determination of the title compound was carried out to confirm its successful synthesis.
The title compound is in an extended conformation. The COOH group does not form hydrogen-bonded carboxy dimers, but forms an intermolecular hydrogen bond with the carbonyl O5 atom. The lysine N1 atom is pyramidal, and forms a bifurcated intramolecular hydrogen bond with the carboxy O3 and nitro O8 atoms.
The cell dimensions of the title compound at 296 K are a = 11.8092 (13), b = 34.832 (4), c = 5.4033 (6) Å and V = 2222.6 (7) Å3.