Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807029418/wk2061sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807029418/wk2061Isup2.hkl |
CCDC reference: 655035
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.004 Å
- R factor = 0.038
- wR factor = 0.099
- Data-to-parameter ratio = 11.0
checkCIF/PLATON results
No syntax errors found
Alert level C STRVA01_ALERT_4_C Flack test results are meaningless. From the CIF: _refine_ls_abs_structure_Flack 0.000 From the CIF: _refine_ls_abs_structure_Flack_su 10.000 PLAT032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ... 10.00 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.79 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.19 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C18 PLAT412_ALERT_2_C Short Intra XH3 .. XHn H14A .. H16 .. 1.85 Ang. PLAT420_ALERT_2_C D-H Without Acceptor N2 - H2A ... ? PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 10.00
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.07 From the CIF: _reflns_number_total 3277 Count of symmetry unique reflns 3287 Completeness (_total/calc) 99.70% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C16 = . S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Schmidt & Potzolli (1987); McKeever & Pattenden (2003).
N-Methyl-L-Leucine benzyl ester Toluene Sulfonic acid (0.82 g, 2 mmol) and diisopropylethylamine (1.3 ml, 7.2 mmol) were added to dichloromethane (5 ml) at room temperature under an atmosphere of nitrogen, On dissolution, the mixture was cooled to 273 K, then 1-hydroxybenzotriazole (0.30 g, 2.2 mmol) and tert-Butoxycarbonyl-L– Leucine (0.46 g, 2 mmol) were added successively. After 15 minutes, N,N'-dicyclohexylcarbodiimide (0.45 g, 2.2 mmol) with dichloromethane (2 ml) was added dropwise to the mixture. The reaction was stirred at 273 K for 2 h under an atmosphere of nitrogen and allowed to warm to room temperature over the course of 12 h, filtered, and the solvent removed by distillation under reduced pressure. The mixture was dissolved in EtOAc (60 ml), then was washed with 10% citric acid (40 ml), saturated NaHCO3 (40 ml), and brine (40 ml), with backwashing. The combined organic extracts were dried (NaSO4) and concentrated. The crude was purified by silica-gel chromatography with acetone-hexane (1:3) to give the title compound. Colorless crystals suitable for X-ray analysis (m.p.331 K) grew over a period of one week when the solution was exposed to air.
Hydrogen atoms attached to C or N atoms were located at geometrically calculated positions [0.95 (CH), 0.99 (CH2), 0.98 (CH3), 0.88 (NH)] and refined with isotropic thermal parameters Uiso(H) equal to 1.2 for CH2, CH, and NH, 1.5 for CH3 Ueq(C atoms).
Amino acid derivatives are used generally for the synthesis of polypeptides. The title compound, (I), is a product of the reaction of two L-Leucine derivatives. It is a precursor for dipeptides, an intermediate product in the synthesis of polypeptides. We report here its crystal structure. The bond lengths and angles are unexceptional and are in good agreement with the corresponding values in L-Valine, N-[N-[(1,1-dimethylethoxy)carbonyl]-L-leucyl]-N-methyl-phenylmethyl ester (Schmidt et al.,1987)
For related literature, see: Schmidt & Potzolli (1987); McKeever & Pattenden (2003).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
Fig. 1. The asymmetric unit of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. |
C25H40N2O5 | Dx = 1.122 Mg m−3 |
Mr = 448.59 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 13652 reflections |
a = 9.9400 (12) Å | θ = 12–18° |
b = 14.9395 (18) Å | µ = 0.08 mm−1 |
c = 17.876 (2) Å | T = 173 K |
V = 2654.6 (5) Å3 | Block, colourless |
Z = 4 | 0.50 × 0.40 × 0.20 mm |
F(000) = 976 |
Bruker SMART 1000 CCD diffractometer | 3277 independent reflections |
Radiation source: fine-focus sealed tube | 2732 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
ω scans | θmax = 27.1°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→12 |
Tmin = 0.96, Tmax = 0.99 | k = −17→19 |
13652 measured reflections | l = −22→13 |
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)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.099 | w = 1/[σ2(Fo2) + (0.0448P)2 + 0.6524P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
3277 reflections | Δρmax = 0.28 e Å−3 |
298 parameters | Δρmin = −0.24 e Å−3 |
0 restraints | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0 (10) |
C25H40N2O5 | V = 2654.6 (5) Å3 |
Mr = 448.59 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 9.9400 (12) Å | µ = 0.08 mm−1 |
b = 14.9395 (18) Å | T = 173 K |
c = 17.876 (2) Å | 0.50 × 0.40 × 0.20 mm |
Bruker SMART 1000 CCD diffractometer | 3277 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2732 reflections with I > 2σ(I) |
Tmin = 0.96, Tmax = 0.99 | Rint = 0.026 |
13652 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | H-atom parameters constrained |
wR(F2) = 0.099 | Δρmax = 0.28 e Å−3 |
S = 1.04 | Δρmin = −0.24 e Å−3 |
3277 reflections | Absolute structure: Flack (1983) |
298 parameters | Absolute structure parameter: 0 (10) |
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 | ||
O1 | 0.12084 (16) | 0.18042 (11) | 0.90469 (9) | 0.0411 (4) | |
O2 | −0.03295 (18) | 0.07107 (12) | 0.90142 (9) | 0.0455 (4) | |
O3 | 0.28053 (14) | 0.19630 (10) | 1.09159 (9) | 0.0370 (4) | |
O4 | 0.13473 (17) | 0.20856 (11) | 1.26427 (9) | 0.0442 (4) | |
O5 | 0.32332 (16) | 0.28696 (10) | 1.29608 (8) | 0.0359 (3) | |
N1 | 0.06472 (18) | 0.16720 (12) | 1.05938 (9) | 0.0294 (4) | |
N2 | 0.20996 (18) | 0.32424 (11) | 1.19348 (9) | 0.0309 (4) | |
H2A | 0.2604 | 0.3726 | 1.1918 | 0.037* | |
C1 | 0.1431 (2) | 0.29670 (15) | 0.81465 (11) | 0.0356 (5) | |
C2 | 0.2561 (2) | 0.29855 (17) | 0.76974 (13) | 0.0430 (6) | |
H2 | 0.2889 | 0.2446 | 0.7484 | 0.052* | |
C3 | 0.3219 (3) | 0.37837 (19) | 0.75561 (15) | 0.0535 (7) | |
H3 | 0.4009 | 0.3789 | 0.7257 | 0.064* | |
C4 | 0.2730 (3) | 0.45650 (18) | 0.78484 (16) | 0.0556 (7) | |
H4 | 0.3168 | 0.5115 | 0.7741 | 0.067* | |
C5 | 0.1610 (3) | 0.45576 (18) | 0.82960 (15) | 0.0547 (7) | |
H5 | 0.1284 | 0.5102 | 0.8503 | 0.066* | |
C6 | 0.0957 (3) | 0.37666 (18) | 0.84466 (14) | 0.0455 (6) | |
H6 | 0.0180 | 0.3766 | 0.8756 | 0.055* | |
C7 | 0.0715 (3) | 0.21184 (19) | 0.83221 (13) | 0.0483 (6) | |
H7A | −0.0268 | 0.2224 | 0.8345 | 0.058* | |
H7B | 0.0896 | 0.1666 | 0.7931 | 0.058* | |
C8 | 0.0554 (2) | 0.11038 (15) | 0.93323 (12) | 0.0332 (5) | |
C9 | 0.1060 (2) | 0.09157 (14) | 1.01228 (12) | 0.0312 (5) | |
H9 | 0.2066 | 0.0897 | 1.0110 | 0.037* | |
C10 | 0.0552 (3) | 0.00139 (15) | 1.04099 (13) | 0.0386 (5) | |
H10A | −0.0443 | 0.0023 | 1.0407 | 0.046* | |
H10B | 0.0846 | −0.0458 | 1.0057 | 0.046* | |
C11 | 0.1025 (3) | −0.02395 (16) | 1.11929 (14) | 0.0421 (6) | |
H11 | 0.0708 | 0.0231 | 1.1550 | 0.051* | |
C12 | 0.2542 (3) | −0.0303 (2) | 1.12513 (19) | 0.0654 (9) | |
H12A | 0.2794 | −0.0458 | 1.1765 | 0.098* | |
H12B | 0.2943 | 0.0275 | 1.1118 | 0.098* | |
H12C | 0.2871 | −0.0765 | 1.0909 | 0.098* | |
C13 | 0.0378 (3) | −0.11314 (18) | 1.14157 (17) | 0.0578 (7) | |
H13A | 0.0685 | −0.1603 | 1.1075 | 0.087* | |
H13B | −0.0603 | −0.1079 | 1.1385 | 0.087* | |
H13C | 0.0639 | −0.1283 | 1.1929 | 0.087* | |
C14 | −0.0782 (2) | 0.19081 (16) | 1.05734 (13) | 0.0358 (5) | |
H14A | −0.0990 | 0.2310 | 1.0991 | 0.054* | |
H14B | −0.1326 | 0.1363 | 1.0616 | 0.054* | |
H14C | −0.0987 | 0.2209 | 1.0100 | 0.054* | |
C15 | 0.1613 (2) | 0.21621 (14) | 1.09387 (11) | 0.0283 (4) | |
C16 | 0.1177 (2) | 0.30299 (14) | 1.13349 (11) | 0.0305 (4) | |
H16 | 0.0252 | 0.2951 | 1.1544 | 0.037* | |
C17 | 0.1162 (2) | 0.37809 (14) | 1.07518 (12) | 0.0350 (5) | |
H17A | 0.2078 | 0.3836 | 1.0539 | 0.042* | |
H17B | 0.0554 | 0.3601 | 1.0340 | 0.042* | |
C18 | 0.0725 (3) | 0.46975 (15) | 1.10310 (14) | 0.0422 (6) | |
H18 | 0.1339 | 0.4868 | 1.1451 | 0.051* | |
C19 | 0.0895 (4) | 0.53893 (19) | 1.04158 (19) | 0.0790 (11) | |
H19A | 0.0306 | 0.5239 | 0.9995 | 0.118* | |
H19B | 0.1833 | 0.5393 | 1.0247 | 0.118* | |
H19C | 0.0657 | 0.5982 | 1.0609 | 0.118* | |
C20 | −0.0700 (3) | 0.4701 (2) | 1.1334 (2) | 0.0774 (10) | |
H20A | −0.0941 | 0.5309 | 1.1491 | 0.116* | |
H20B | −0.0759 | 0.4296 | 1.1764 | 0.116* | |
H20C | −0.1322 | 0.4501 | 1.0942 | 0.116* | |
C21 | 0.2165 (2) | 0.26697 (14) | 1.25290 (11) | 0.0321 (5) | |
C22 | 0.3583 (3) | 0.22819 (16) | 1.36006 (12) | 0.0393 (5) | |
C23 | 0.3851 (3) | 0.13377 (16) | 1.33291 (15) | 0.0472 (6) | |
H23A | 0.3015 | 0.1077 | 1.3136 | 0.071* | |
H23B | 0.4184 | 0.0973 | 1.3746 | 0.071* | |
H23C | 0.4526 | 0.1352 | 1.2930 | 0.071* | |
C24 | 0.4868 (3) | 0.2711 (2) | 1.38889 (14) | 0.0510 (7) | |
H24A | 0.5550 | 0.2707 | 1.3493 | 0.077* | |
H24B | 0.5200 | 0.2374 | 1.4321 | 0.077* | |
H24C | 0.4683 | 0.3330 | 1.4038 | 0.077* | |
C25 | 0.2492 (3) | 0.2326 (2) | 1.41909 (13) | 0.0526 (7) | |
H25A | 0.2336 | 0.2951 | 1.4332 | 0.079* | |
H25B | 0.2775 | 0.1986 | 1.4632 | 0.079* | |
H25C | 0.1659 | 0.2069 | 1.3991 | 0.079* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0439 (9) | 0.0468 (9) | 0.0326 (8) | −0.0112 (8) | −0.0077 (7) | 0.0088 (7) |
O2 | 0.0539 (10) | 0.0452 (9) | 0.0373 (9) | −0.0129 (8) | −0.0068 (8) | −0.0034 (8) |
O3 | 0.0272 (7) | 0.0380 (8) | 0.0458 (9) | 0.0041 (7) | −0.0032 (7) | −0.0059 (7) |
O4 | 0.0431 (9) | 0.0488 (9) | 0.0407 (8) | −0.0132 (8) | −0.0019 (7) | 0.0063 (8) |
O5 | 0.0406 (8) | 0.0360 (8) | 0.0311 (7) | −0.0047 (7) | −0.0068 (7) | 0.0043 (6) |
N1 | 0.0287 (9) | 0.0310 (9) | 0.0284 (9) | 0.0014 (7) | −0.0005 (7) | −0.0022 (7) |
N2 | 0.0367 (10) | 0.0289 (8) | 0.0271 (8) | −0.0026 (8) | −0.0032 (8) | −0.0026 (7) |
C1 | 0.0341 (11) | 0.0461 (13) | 0.0267 (10) | −0.0002 (10) | −0.0056 (9) | 0.0064 (10) |
C2 | 0.0451 (14) | 0.0469 (13) | 0.0369 (12) | 0.0114 (12) | 0.0053 (10) | 0.0070 (11) |
C3 | 0.0443 (14) | 0.0694 (18) | 0.0467 (14) | −0.0038 (14) | 0.0087 (12) | 0.0197 (14) |
C4 | 0.0688 (18) | 0.0471 (14) | 0.0509 (15) | −0.0118 (14) | −0.0053 (15) | 0.0139 (12) |
C5 | 0.075 (2) | 0.0459 (14) | 0.0431 (14) | 0.0111 (14) | −0.0044 (15) | 0.0000 (12) |
C6 | 0.0387 (13) | 0.0632 (16) | 0.0347 (12) | 0.0113 (12) | 0.0022 (10) | 0.0015 (12) |
C7 | 0.0532 (15) | 0.0568 (15) | 0.0347 (12) | −0.0120 (13) | −0.0110 (11) | 0.0090 (12) |
C8 | 0.0344 (11) | 0.0342 (11) | 0.0311 (11) | −0.0001 (10) | 0.0021 (9) | −0.0032 (9) |
C9 | 0.0326 (11) | 0.0301 (10) | 0.0308 (11) | 0.0003 (9) | −0.0010 (9) | −0.0019 (9) |
C10 | 0.0446 (13) | 0.0311 (11) | 0.0402 (12) | −0.0009 (10) | −0.0019 (11) | 0.0005 (10) |
C11 | 0.0517 (15) | 0.0335 (11) | 0.0410 (13) | 0.0019 (11) | −0.0005 (11) | 0.0062 (10) |
C12 | 0.0542 (17) | 0.0611 (18) | 0.081 (2) | 0.0023 (15) | −0.0153 (16) | 0.0268 (17) |
C13 | 0.0694 (18) | 0.0442 (14) | 0.0598 (17) | −0.0029 (14) | 0.0034 (15) | 0.0181 (13) |
C14 | 0.0291 (11) | 0.0427 (12) | 0.0356 (11) | −0.0001 (10) | −0.0001 (9) | −0.0047 (10) |
C15 | 0.0287 (10) | 0.0298 (10) | 0.0263 (9) | 0.0005 (9) | −0.0009 (8) | 0.0021 (8) |
C16 | 0.0296 (10) | 0.0344 (11) | 0.0277 (10) | 0.0023 (9) | −0.0031 (8) | −0.0029 (9) |
C17 | 0.0430 (12) | 0.0327 (11) | 0.0291 (11) | 0.0056 (10) | −0.0020 (9) | −0.0006 (9) |
C18 | 0.0509 (14) | 0.0367 (12) | 0.0391 (12) | 0.0109 (11) | −0.0098 (11) | −0.0039 (10) |
C19 | 0.122 (3) | 0.0391 (15) | 0.076 (2) | 0.0218 (18) | 0.007 (2) | 0.0129 (15) |
C20 | 0.070 (2) | 0.0630 (19) | 0.099 (3) | 0.0282 (18) | 0.015 (2) | −0.0043 (19) |
C21 | 0.0346 (11) | 0.0328 (10) | 0.0289 (10) | −0.0005 (10) | 0.0000 (9) | −0.0040 (9) |
C22 | 0.0455 (13) | 0.0452 (13) | 0.0273 (10) | 0.0016 (11) | −0.0029 (10) | 0.0074 (10) |
C23 | 0.0542 (15) | 0.0419 (13) | 0.0455 (14) | 0.0040 (12) | 0.0051 (12) | 0.0097 (11) |
C24 | 0.0533 (15) | 0.0618 (16) | 0.0379 (12) | 0.0003 (13) | −0.0126 (12) | 0.0063 (12) |
C25 | 0.0579 (16) | 0.0675 (17) | 0.0323 (12) | 0.0099 (14) | 0.0044 (11) | 0.0084 (12) |
O1—C8 | 1.333 (3) | C12—H12A | 0.9800 |
O1—C7 | 1.463 (3) | C12—H12B | 0.9800 |
O2—C8 | 1.200 (3) | C12—H12C | 0.9800 |
O3—C15 | 1.223 (2) | C13—H13A | 0.9800 |
O4—C21 | 1.210 (3) | C13—H13B | 0.9800 |
O5—C21 | 1.346 (3) | C13—H13C | 0.9800 |
O5—C22 | 1.483 (3) | C14—H14A | 0.9800 |
N1—C15 | 1.356 (3) | C14—H14B | 0.9800 |
N1—C14 | 1.464 (3) | C14—H14C | 0.9800 |
N1—C9 | 1.468 (3) | C15—C16 | 1.539 (3) |
N2—C21 | 1.365 (3) | C16—C17 | 1.531 (3) |
N2—C16 | 1.446 (3) | C16—H16 | 1.0000 |
N2—H2A | 0.8800 | C17—C18 | 1.521 (3) |
C1—C2 | 1.381 (3) | C17—H17A | 0.9900 |
C1—C6 | 1.392 (3) | C17—H17B | 0.9900 |
C1—C7 | 1.488 (3) | C18—C20 | 1.517 (4) |
C2—C3 | 1.383 (4) | C18—C19 | 1.519 (4) |
C2—H2 | 0.9500 | C18—H18 | 1.0000 |
C3—C4 | 1.368 (4) | C19—H19A | 0.9800 |
C3—H3 | 0.9500 | C19—H19B | 0.9800 |
C4—C5 | 1.370 (4) | C19—H19C | 0.9800 |
C4—H4 | 0.9500 | C20—H20A | 0.9800 |
C5—C6 | 1.375 (4) | C20—H20B | 0.9800 |
C5—H5 | 0.9500 | C20—H20C | 0.9800 |
C6—H6 | 0.9500 | C22—C25 | 1.514 (3) |
C7—H7A | 0.9900 | C22—C23 | 1.515 (3) |
C7—H7B | 0.9900 | C22—C24 | 1.519 (4) |
C8—C9 | 1.526 (3) | C23—H23A | 0.9800 |
C9—C10 | 1.528 (3) | C23—H23B | 0.9800 |
C9—H9 | 1.0000 | C23—H23C | 0.9800 |
C10—C11 | 1.524 (3) | C24—H24A | 0.9800 |
C10—H10A | 0.9900 | C24—H24B | 0.9800 |
C10—H10B | 0.9900 | C24—H24C | 0.9800 |
C11—C12 | 1.515 (4) | C25—H25A | 0.9800 |
C11—C13 | 1.532 (3) | C25—H25B | 0.9800 |
C11—H11 | 1.0000 | C25—H25C | 0.9800 |
C8—O1—C7 | 115.28 (18) | N1—C14—H14B | 109.5 |
C21—O5—C22 | 119.72 (17) | H14A—C14—H14B | 109.5 |
C15—N1—C14 | 124.62 (18) | N1—C14—H14C | 109.5 |
C15—N1—C9 | 118.60 (18) | H14A—C14—H14C | 109.5 |
C14—N1—C9 | 116.28 (18) | H14B—C14—H14C | 109.5 |
C21—N2—C16 | 118.01 (17) | O3—C15—N1 | 122.7 (2) |
C21—N2—H2A | 121.0 | O3—C15—C16 | 119.51 (18) |
C16—N2—H2A | 121.0 | N1—C15—C16 | 117.73 (18) |
C2—C1—C6 | 118.8 (2) | N2—C16—C17 | 110.50 (17) |
C2—C1—C7 | 121.9 (2) | N2—C16—C15 | 110.36 (16) |
C6—C1—C7 | 119.2 (2) | C17—C16—C15 | 107.86 (16) |
C1—C2—C3 | 120.5 (2) | N2—C16—H16 | 109.4 |
C1—C2—H2 | 119.7 | C17—C16—H16 | 109.4 |
C3—C2—H2 | 119.7 | C15—C16—H16 | 109.4 |
C4—C3—C2 | 119.8 (2) | C18—C17—C16 | 116.04 (18) |
C4—C3—H3 | 120.1 | C18—C17—H17A | 108.3 |
C2—C3—H3 | 120.1 | C16—C17—H17A | 108.3 |
C3—C4—C5 | 120.3 (3) | C18—C17—H17B | 108.3 |
C3—C4—H4 | 119.8 | C16—C17—H17B | 108.3 |
C5—C4—H4 | 119.8 | H17A—C17—H17B | 107.4 |
C4—C5—C6 | 120.3 (3) | C20—C18—C19 | 111.1 (3) |
C4—C5—H5 | 119.8 | C20—C18—C17 | 112.8 (2) |
C6—C5—H5 | 119.8 | C19—C18—C17 | 110.1 (2) |
C5—C6—C1 | 120.1 (2) | C20—C18—H18 | 107.5 |
C5—C6—H6 | 119.9 | C19—C18—H18 | 107.5 |
C1—C6—H6 | 119.9 | C17—C18—H18 | 107.5 |
O1—C7—C1 | 107.45 (19) | C18—C19—H19A | 109.5 |
O1—C7—H7A | 110.2 | C18—C19—H19B | 109.5 |
C1—C7—H7A | 110.2 | H19A—C19—H19B | 109.5 |
O1—C7—H7B | 110.2 | C18—C19—H19C | 109.5 |
C1—C7—H7B | 110.2 | H19A—C19—H19C | 109.5 |
H7A—C7—H7B | 108.5 | H19B—C19—H19C | 109.5 |
O2—C8—O1 | 124.0 (2) | C18—C20—H20A | 109.5 |
O2—C8—C9 | 126.2 (2) | C18—C20—H20B | 109.5 |
O1—C8—C9 | 109.76 (18) | H20A—C20—H20B | 109.5 |
N1—C9—C8 | 107.28 (17) | C18—C20—H20C | 109.5 |
N1—C9—C10 | 113.18 (18) | H20A—C20—H20C | 109.5 |
C8—C9—C10 | 111.39 (18) | H20B—C20—H20C | 109.5 |
N1—C9—H9 | 108.3 | O4—C21—O5 | 126.4 (2) |
C8—C9—H9 | 108.3 | O4—C21—N2 | 123.4 (2) |
C10—C9—H9 | 108.3 | O5—C21—N2 | 110.16 (18) |
C11—C10—C9 | 115.2 (2) | O5—C22—C25 | 110.11 (19) |
C11—C10—H10A | 108.5 | O5—C22—C23 | 110.19 (18) |
C9—C10—H10A | 108.5 | C25—C22—C23 | 112.9 (2) |
C11—C10—H10B | 108.5 | O5—C22—C24 | 102.04 (19) |
C9—C10—H10B | 108.5 | C25—C22—C24 | 110.3 (2) |
H10A—C10—H10B | 107.5 | C23—C22—C24 | 110.7 (2) |
C12—C11—C10 | 112.7 (2) | C22—C23—H23A | 109.5 |
C12—C11—C13 | 110.2 (2) | C22—C23—H23B | 109.5 |
C10—C11—C13 | 109.0 (2) | H23A—C23—H23B | 109.5 |
C12—C11—H11 | 108.3 | C22—C23—H23C | 109.5 |
C10—C11—H11 | 108.3 | H23A—C23—H23C | 109.5 |
C13—C11—H11 | 108.3 | H23B—C23—H23C | 109.5 |
C11—C12—H12A | 109.5 | C22—C24—H24A | 109.5 |
C11—C12—H12B | 109.5 | C22—C24—H24B | 109.5 |
H12A—C12—H12B | 109.5 | H24A—C24—H24B | 109.5 |
C11—C12—H12C | 109.5 | C22—C24—H24C | 109.5 |
H12A—C12—H12C | 109.5 | H24A—C24—H24C | 109.5 |
H12B—C12—H12C | 109.5 | H24B—C24—H24C | 109.5 |
C11—C13—H13A | 109.5 | C22—C25—H25A | 109.5 |
C11—C13—H13B | 109.5 | C22—C25—H25B | 109.5 |
H13A—C13—H13B | 109.5 | H25A—C25—H25B | 109.5 |
C11—C13—H13C | 109.5 | C22—C25—H25C | 109.5 |
H13A—C13—H13C | 109.5 | H25A—C25—H25C | 109.5 |
H13B—C13—H13C | 109.5 | H25B—C25—H25C | 109.5 |
N1—C14—H14A | 109.5 |
Experimental details
Crystal data | |
Chemical formula | C25H40N2O5 |
Mr | 448.59 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 173 |
a, b, c (Å) | 9.9400 (12), 14.9395 (18), 17.876 (2) |
V (Å3) | 2654.6 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.50 × 0.40 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART 1000 CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.96, 0.99 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13652, 3277, 2732 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.640 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.099, 1.04 |
No. of reflections | 3277 |
No. of parameters | 298 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.28, −0.24 |
Absolute structure | Flack (1983) |
Absolute structure parameter | 0 (10) |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
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Amino acid derivatives are used generally for the synthesis of polypeptides. The title compound, (I), is a product of the reaction of two L-Leucine derivatives. It is a precursor for dipeptides, an intermediate product in the synthesis of polypeptides. We report here its crystal structure. The bond lengths and angles are unexceptional and are in good agreement with the corresponding values in L-Valine, N-[N-[(1,1-dimethylethoxy)carbonyl]-L-leucyl]-N-methyl-phenylmethyl ester (Schmidt et al.,1987)