Benzyl 2-{[2-(tert-butoxy­carbonyl­amino)-4-methyl­penta­noyl]methyl­amino}-4-methyl­penta­noate

Liao, X.-J.; Xu, W.-J.; Xu, S.-H.; Dong, F.-F.

doi:10.1107/S1600536807029418

Benzyl 2-{[2-(tert-butoxycarbonylamino)-4-methylpentanoyl]methylamino}-4-methylpentanoate

X.-J. Liao, W.-J. Xu, S.-H. Xu and F.-F. Dong

The title compound, C₂₅H₄₀N₂O₅, was synthesized in 55.9% yield by condensation of N-methyl-L-leucine benzyl ester toluene sulfonic acid with tert-butoxycarbonyl-L-leucine at 273 K and its crystal structure determined. The dipeptide derivative conjugates through the amide linkage and includes two protecting groups, a tert-butyloxycarbonyl group at the C-tip and a benzyl group at the N-tip.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807029418/wk2061sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807029418/wk2061Isup2.hkl Contains datablock I

CCDC reference: 655035

checkCIF report

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

Comment top

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)

Related literature top

For related literature, see: Schmidt & Potzolli (1987); McKeever & Pattenden (2003).

Experimental top

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.

Structure description top

For related literature, see: Schmidt & Potzolli (1987); McKeever & Pattenden (2003).

Computing details top

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.

Figures top

Fig. 1. The asymmetric unit of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

Benzyl 2-{[2-(tert-butoxycarbonylamino)-4-methylpentanoyl]methylamino}- 4-methylpentanoate top

Crystal data top

C₂₅H₄₀N₂O₅	D_x = 1.122 Mg m⁻³
M_r = 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

Data collection top

Bruker SMART 1000 CCD diffractometer	3277 independent reflections
Radiation source: fine-focus sealed tube	2732 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω scans	θ_max = 27.1°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→12
T_min = 0.96, T_max = 0.99	k = −17→19
13652 measured reflections	l = −22→13

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)] = 0.038	H-atom parameters constrained
wR(F²) = 0.099	w = 1/[σ²(F_o²) + (0.0448P)² + 0.6524P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
3277 reflections	Δρ_max = 0.28 e Å⁻³
298 parameters	Δρ_min = −0.24 e Å⁻³
0 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0 (10)

Crystal data top

C₂₅H₄₀N₂O₅	V = 2654.6 (5) Å³
M_r = 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

Data collection top

Bruker SMART 1000 CCD diffractometer	3277 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2732 reflections with I > 2σ(I)
T_min = 0.96, T_max = 0.99	R_int = 0.026
13652 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.099	Δρ_max = 0.28 e Å⁻³
S = 1.04	Δρ_min = −0.24 e Å⁻³
3277 reflections	Absolute structure: Flack (1983)
298 parameters	Absolute structure parameter: 0 (10)
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.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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
M_r	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)
T_min, T_max	0.96, 0.99
No. of measured, independent and observed [I > 2σ(I)] reflections	13652, 3277, 2732
R_int	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
Δρ_max, Δρ_min (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.

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

Benzyl 2-{[2-(tert-butoxy­carbonyl­amino)-4-methyl­penta­noyl]methyl­amino}-4-methyl­penta­noate

Supporting information

Key indicators

checkCIF/PLATON results

Benzyl 2-{[2-(tert-butoxycarbonylamino)-4-methylpentanoyl]methylamino}-4-methylpentanoate