An N-protected depsipeptide free acid prepared by direct synthesis without using a terminal-C protecting group: tert-butoxy­carbonyl-l-alanyl-l-leucyl-l-lactic acid (Boc-l-Ala-l-Leu-l-Lac-OH)

Oku, H.; Yamada, K.; Katakai, R.

doi:10.1107/S1600536804010189

An N-protected depsipeptide free acid prepared by direct synthesis without using a terminal-C protecting group: tert-butoxycarbonyl-L-alanyl-L-leucyl-L-lactic acid (Boc-L-Ala-L-Leu-L-Lac-OH)

Crystals of the title compound, C₁₇H₃₀N₂O₇, were successfully grown from ethyl acetate at room temperature. In the crystal structure, a free carboxylic acid group is found at the terminal C atom. The free acid —OH group contributes to a hydrogen-bond network, together with two N—H

O interactions, forming tight packing.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804010189/ww6184sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536804010189/ww6184Isup2.hkl Contains datablock I

CCDC reference: 242297

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.009 Å
R factor = 0.068
wR factor = 0.156
Data-to-parameter ratio = 8.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) .......          9

Author Response: Because of the limited numbers of observed reflections. Even at the low temperature condition (173 K), diffractions from the crystal of (I) were too weak to collect enough numbers. Therefore only main-chain atoms were refined anisotropically.


Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97

Author Response: This is due to the data collection by rotation around a spindle axis on our image-plate system.

PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C11

Author Response: It is due to the difference of thermal mobility. The atoms located at chain-ends and amino-acid side chains often show higer U(eq) compared with the atoms located inside of the molecule.

PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9

Author Response: The chain end atoms (-OEt) often show lower bond precision due to their higher thermal mobility compared with the atoms located inside of the chain.


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           68.09
           From the CIF: _reflns_number_total               1963
           Count of symmetry unique reflns         2026
           Completeness (_total/calc)             96.89%
           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

Author Response: All the Friedel pairs have been averaged during the refinement process.


   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: RAPID-AUTO (Rigaku/MSC and Rigaku, 2003); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC and Rigaku, 2003); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: ORTEP (Johnson, 1965); software used to prepare material for publication: CrystalStructure.

tert-Butyloxycarbonyl-L-Alanyl-L-Leucyl-L-Lactic Acid top

Crystal data top

C₁₇H₃₀N₂O₇	F(000) = 404.00
M_r = 374.43	D_x = 1.189 Mg m⁻³
Monoclinic, P2₁	Melting point = 414–415 K
Hall symbol: P 2yb	Cu Kα radiation, λ = 1.5418 Å
a = 8.826 (2) Å	Cell parameters from 8126 reflections
b = 10.951 (2) Å	θ = 4.0–67.9°
c = 11.043 (2) Å	µ = 0.77 mm⁻¹
β = 101.57 (2)°	T = 173 K
V = 1045.7 (4) Å³	Needle, colorless
Z = 2	0.40 × 0.05 × 0.05 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	1437 reflections with F² > 2σ(F²)
Detector resolution: 10.00 pixels mm^-1	R_int = 0.051
ω scans	θ_max = 68.1°
Absorption correction: part of the refinement model (ΔF) (DIFABS; Walker & Stuart, 1983)	h = −10→10
T_min = 0.672, T_max = 0.962	k = −12→12
16364 measured reflections	l = −13→12
1963 independent reflections

Refinement top

Refinement on F²	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.068	w = 1/[0.001F_o² + 3σ(F_o²) + 0.5]/(4F_o²)
wR(F²) = 0.156	(Δ/σ)_max = 0.009
S = 1.26	Δρ_max = 0.36 e Å⁻³
1963 reflections	Δρ_min = −0.38 e Å⁻³
220 parameters

Special details top

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	U_iso*/U_eq
O(11)	0.4513 (5)	−0.0260 (4)	−0.2540 (4)	0.066 (1)
O(12)	0.3843 (5)	0.1449 (5)	−0.1616 (4)	0.077 (2)
O(21)	0.5131 (4)	0.1666 (4)	0.2000 (4)	0.068 (2)
O(31)	0.8967 (5)	0.1891 (5)	0.0104 (4)	0.078 (2)
O(41)	0.9410 (4)	0.2944 (4)	0.1896 (3)	0.051 (1)
O(42)	1.2559 (5)	0.3617 (4)	0.0479 (4)	0.071 (2)
O(43)	1.2383 (4)	0.2441 (4)	0.2089 (4)	0.058 (1)
N(21)	0.4243 (5)	−0.0353 (5)	−0.0620 (4)	0.052 (2)
N(31)	0.6761 (5)	0.0530 (5)	0.1143 (5)	0.055 (2)
C(11)	0.4375 (7)	0.0256 (6)	−0.3761 (6)	0.061 (2)
C(12)	0.2725 (9)	0.0701 (8)	−0.4251 (7)	0.099 (3)*
C(13)	0.5516 (8)	0.1260 (8)	−0.3771 (7)	0.096 (3)*
C(14)	0.4700 (9)	−0.0796 (8)	−0.4541 (7)	0.084 (2)*
C(15)	0.4149 (7)	0.0385 (7)	−0.1619 (6)	0.057 (2)
C(21)	0.3997 (6)	0.0136 (6)	0.0559 (5)	0.051 (2)
C(22)	0.5346 (7)	0.0870 (6)	0.1261 (6)	0.053 (2)
C(23)	0.3660 (8)	−0.0885 (7)	0.1361 (6)	0.071 (2)*
C(31)	0.8139 (6)	0.1048 (6)	0.1881 (5)	0.051 (2)
C(32)	0.8841 (6)	0.1995 (6)	0.1152 (6)	0.055 (2)
C(33)	0.9375 (7)	0.0062 (5)	0.2291 (5)	0.054 (2)*
C(34)	0.8901 (7)	−0.1000 (6)	0.3008 (5)	0.056 (2)*
C(35)	0.8427 (8)	−0.0601 (8)	0.4170 (6)	0.083 (2)*
C(36)	1.0263 (8)	−0.1905 (7)	0.3301 (6)	0.072 (2)*
C(41)	1.0299 (7)	0.3786 (6)	0.1317 (5)	0.056 (2)
C(42)	1.1866 (7)	0.3280 (6)	0.1261 (6)	0.052 (2)
C(43)	1.0440 (7)	0.4927 (6)	0.2085 (6)	0.068 (2)*
H(1)	0.2461	0.1295	−0.3702	0.119*
H(2)	0.2627	0.1047	−0.5052	0.119*
H(3)	0.2049	0.0020	−0.4289	0.119*
H(4)	0.6527	0.0933	−0.3521	0.115*
H(5)	0.5404	0.1596	−0.4577	0.115*
H(6)	0.5356	0.1881	−0.3209	0.115*
H(7)	0.3976	−0.1430	−0.4506	0.101*
H(8)	0.4638	−0.0557	−0.5377	0.101*
H(9)	0.5714	−0.1081	−0.4208	0.101*
H(10)	0.4469	−0.1196	−0.0684	0.062*
H(11)	0.3114	0.0651	0.0381	0.060*
H(12)	0.3483	−0.0538	0.2109	0.085*
H(13)	0.2781	−0.1346	0.0982	0.085*
H(14)	0.4540	−0.1404	0.1536	0.085*
H(15)	0.6874	−0.0067	0.0543	0.066*
H(16)	0.7879	0.1408	0.2595	0.062*
H(17)	0.9639	−0.0239	0.1554	0.065*
H(18)	1.0257	0.0433	0.2791	0.065*
H(19)	0.8046	−0.1393	0.2496	0.068*
H(20)	0.9275	−0.0212	0.4694	0.100*
H(21)	0.7594	−0.0040	0.3963	0.100*
H(22)	0.8106	−0.1283	0.4588	0.100*
H(23)	0.9968	−0.2596	0.3719	0.087*
H(24)	1.0529	−0.2158	0.2547	0.087*
H(25)	1.1129	−0.1521	0.3807	0.087*
H(26)	0.9760	0.3969	0.0503	0.068*
H(27)	1.0976	0.4724	0.2894	0.082*
H(28)	1.1010	0.5524	0.1741	0.082*
H(29)	0.9448	0.5243	0.2122	0.082*
H(30)	1.3227	0.2053	0.1935	0.072*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O(11)	0.085 (3)	0.058 (3)	0.060 (3)	0.001 (3)	0.030 (2)	−0.007 (2)
O(12)	0.093 (3)	0.066 (4)	0.077 (3)	0.021 (3)	0.028 (3)	0.006 (3)
O(21)	0.047 (2)	0.070 (3)	0.090 (3)	0.008 (2)	0.017 (2)	−0.024 (3)
O(31)	0.093 (3)	0.077 (3)	0.069 (3)	−0.017 (3)	0.032 (3)	−0.012 (3)
O(41)	0.042 (2)	0.059 (3)	0.055 (2)	−0.007 (2)	0.013 (2)	−0.009 (2)
O(42)	0.056 (3)	0.079 (3)	0.084 (3)	−0.006 (2)	0.029 (2)	0.012 (3)
O(43)	0.047 (2)	0.059 (3)	0.073 (3)	0.008 (2)	0.023 (2)	0.007 (3)
N(21)	0.053 (3)	0.048 (3)	0.055 (3)	0.002 (3)	0.010 (2)	−0.002 (3)
N(31)	0.037 (3)	0.058 (3)	0.071 (3)	−0.002 (2)	0.012 (2)	−0.015 (3)
C(11)	0.054 (4)	0.074 (5)	0.055 (4)	0.006 (3)	0.007 (3)	−0.010 (4)
C(15)	0.048 (3)	0.059 (5)	0.064 (4)	0.003 (3)	0.012 (3)	−0.002 (4)
C(21)	0.040 (3)	0.056 (4)	0.055 (3)	0.001 (3)	0.007 (3)	−0.001 (3)
C(22)	0.041 (3)	0.056 (4)	0.062 (4)	0.008 (3)	0.012 (3)	0.002 (4)
C(31)	0.038 (3)	0.063 (4)	0.053 (3)	−0.003 (3)	0.010 (3)	−0.005 (3)
C(32)	0.043 (3)	0.060 (5)	0.062 (4)	−0.002 (3)	0.013 (3)	−0.009 (4)
C(41)	0.052 (4)	0.060 (5)	0.058 (4)	−0.001 (3)	0.015 (3)	−0.003 (4)
C(42)	0.046 (4)	0.042 (4)	0.069 (4)	−0.001 (3)	0.011 (3)	−0.010 (4)

Geometric parameters (Å, º) top

O(11)—C(11)	1.444 (8)	C(12)—H(1)	0.9500
O(11)—C(15)	1.330 (9)	C(12)—H(2)	0.9500
O(12)—C(15)	1.196 (9)	C(12)—H(3)	0.9500
O(21)—C(22)	1.235 (8)	C(13)—H(4)	0.9499
O(31)—C(32)	1.190 (9)	C(13)—H(5)	0.9500
O(41)—C(32)	1.357 (7)	C(13)—H(6)	0.9499
O(41)—C(41)	1.441 (8)	C(14)—H(7)	0.9500
O(42)—C(42)	1.211 (8)	C(14)—H(8)	0.9500
O(43)—C(42)	1.313 (7)	C(14)—H(9)	0.9500
N(21)—C(15)	1.357 (8)	C(21)—H(11)	0.9500
N(21)—C(21)	1.463 (8)	C(23)—H(12)	0.9500
N(31)—C(22)	1.334 (8)	C(23)—H(13)	0.9500
N(31)—C(31)	1.438 (7)	C(23)—H(14)	0.9500
C(11)—C(12)	1.528 (9)	C(31)—H(16)	0.9500
C(11)—C(13)	1.493 (9)	C(33)—H(17)	0.9500
C(11)—C(14)	1.500 (9)	C(33)—H(18)	0.9500
C(21)—C(22)	1.514 (8)	C(34)—H(19)	0.9500
C(21)—C(23)	1.493 (9)	C(35)—H(20)	0.9500
C(31)—C(32)	1.519 (9)	C(35)—H(21)	0.9500
C(31)—C(33)	1.538 (8)	C(35)—H(22)	0.9500
C(33)—C(34)	1.511 (9)	C(36)—H(23)	0.9500
C(34)—C(35)	1.493 (9)	C(36)—H(24)	0.9500
C(34)—C(36)	1.542 (9)	C(36)—H(25)	0.9500
C(41)—C(42)	1.503 (9)	C(41)—H(26)	0.9500
C(41)—C(43)	1.501 (9)	C(43)—H(27)	0.9500
O(43)—H(30)	0.9025	C(43)—H(28)	0.9499
N(21)—H(10)	0.9500	C(43)—H(29)	0.9501
N(31)—H(15)	0.9500

O(11)—C(11)—C(12)	110.6 (6)	C(11)—C(14)—H(8)	111.4811
O(11)—C(11)—C(13)	111.4 (5)	C(11)—C(14)—H(9)	107.6359
O(11)—C(11)—C(14)	104.3 (5)	H(2)—C(12)—H(1)	109.4774
C(15)—O(11)—C(11)	121.2 (5)	H(3)—C(12)—H(1)	109.4731
O(11)—C(15)—O(12)	127.5 (7)	H(3)—C(12)—H(2)	109.4674
O(11)—C(15)—N(21)	108.7 (6)	H(5)—C(13)—H(4)	109.4716
O(12)—C(15)—N(21)	123.7 (6)	H(6)—C(13)—H(4)	109.4717
O(21)—C(22)—C(21)	120.2 (5)	H(6)—C(13)—H(5)	109.4697
O(21)—C(22)—N(31)	122.2 (5)	H(8)—C(14)—H(7)	109.4743
O(31)—C(32)—C(31)	125.3 (6)	H(9)—C(14)—H(7)	109.4728
O(31)—C(32)—O(41)	124.5 (6)	H(9)—C(14)—H(8)	109.4716
O(41)—C(32)—C(31)	110.1 (5)	H(11)—C(21)—C(22)	108.6027
C(41)—O(41)—C(32)	113.0 (5)	H(11)—C(21)—C(23)	108.2909
O(41)—C(41)—C(42)	111.7 (5)	C(21)—C(23)—H(12)	107.6458
O(41)—C(41)—C(43)	105.9 (5)	C(21)—C(23)—H(14)	108.4345
O(42)—C(42)—O(43)	123.8 (6)	C(21)—C(23)—H(13)	112.2941
O(42)—C(42)—C(41)	121.2 (6)	H(14)—C(23)—H(12)	109.4714
O(43)—C(42)—C(41)	115.0 (6)	H(13)—C(23)—H(12)	109.4721
C(21)—N(21)—C(15)	120.6 (5)	H(14)—C(23)—H(13)	109.4725
N(21)—C(21)—C(22)	114.1 (5)	H(16)—C(31)—C(32)	110.3690
N(21)—C(21)—C(23)	109.7 (5)	H(16)—C(31)—C(33)	108.8253
N(31)—C(22)—C(21)	117.2 (6)	C(31)—C(33)—H(17)	105.7949
C(31)—N(31)—C(22)	122.4 (5)	C(31)—C(33)—H(18)	108.7055
N(31)—C(31)—C(32)	110.9 (5)	H(17)—C(33)—C(34)	108.8764
N(31)—C(31)—C(33)	111.1 (5)	H(18)—C(33)—C(34)	107.7909
C(13)—C(11)—C(12)	111.0 (6)	C(33)—C(34)—H(19)	107.8834
C(14)—C(11)—C(12)	108.6 (5)	H(18)—C(33)—H(17)	109.4602
C(14)—C(11)—C(13)	110.7 (6)	C(34)—C(35)—H(21)	108.5416
C(23)—C(21)—C(22)	108.9 (5)	H(19)—C(34)—C(35)	108.5357
C(33)—C(31)—C(32)	107.2 (5)	C(34)—C(35)—H(20)	109.3855
C(31)—C(33)—C(34)	116.1 (5)	C(34)—C(35)—H(22)	110.4752
C(33)—C(34)—C(35)	112.3 (6)	H(19)—C(34)—C(36)	109.0651
C(33)—C(34)—C(36)	108.6 (5)	C(34)—C(36)—H(23)	109.6687
C(36)—C(34)—C(35)	110.4 (5)	C(34)—C(36)—H(24)	108.8350
C(43)—C(41)—C(42)	110.9 (5)	C(34)—C(36)—H(25)	109.9062
O(41)—C(41)—H(26)	109.9431	H(21)—C(35)—H(20)	109.4740
H(30)—O(43)—C(42)	112.4693	H(22)—C(35)—H(20)	109.4731
H(10)—N(21)—C(15)	119.7911	H(22)—C(35)—H(21)	109.4722
H(10)—N(21)—C(21)	119.5714	H(24)—C(36)—H(23)	109.4736
N(21)—C(21)—H(11)	107.1832	H(25)—C(36)—H(23)	109.4743
H(15)—N(31)—C(22)	119.4595	H(25)—C(36)—H(24)	109.4676
H(15)—N(31)—C(31)	118.1220	H(26)—C(41)—C(42)	109.1633
N(31)—C(31)—H(16)	108.4598	H(26)—C(41)—C(43)	109.1754
C(11)—C(12)—H(1)	109.2771	C(41)—C(43)—H(27)	107.8421
C(11)—C(12)—H(2)	111.0473	C(41)—C(43)—H(28)	109.7766
C(11)—C(12)—H(3)	108.0712	C(41)—C(43)—H(29)	110.7782
C(11)—C(13)—H(4)	108.4305	H(28)—C(43)—H(27)	109.4694
C(11)—C(13)—H(5)	110.4895	H(29)—C(43)—H(27)	109.4742
C(11)—C(13)—H(6)	109.4878	H(29)—C(43)—H(28)	109.4728
C(11)—C(14)—H(7)	109.2688

O11—C15—N21—C21	176.1 (4)	O(11)—C(11)—C(14)—H(7)	58.8
C15—N21—C21—C22	−75.7 (6)	O(11)—C(11)—C(14)—H(8)	179.9
N21—C21—C22—N31	−32.6 (8)	O(11)—C(11)—C(14)—H(9)	−60.0
C21—C22—N31—C31	−171.8 (5)	C(12)—C(11)—C(14)—H(7)	−59.2
C22—N31—C31—C32	−101.6 (6)	C(12)—C(11)—C(14)—H(8)	62.0
N31—C31—C32—O41	142.0 (5)	C(12)—C(11)—C(14)—H(9)	−178.0
C31—C32—O41—C41	171.1 (4)	C(13)—C(11)—C(14)—H(7)	178.7
C32—O41—C41—C42	−75.1 (5)	C(13)—C(11)—C(14)—H(8)	−60.2
O41—C41—C42—O43	−23.8 (7)	C(13)—C(11)—C(14)—H(9)	59.9
C(15)—O(11)—C(11)—C(12)	−56.7 (7)	H(11)—C(21)—C(22)—O(21)	34.9
C(15)—O(11)—C(11)—C(13)	67.3 (7)	H(11)—C(21)—C(22)—N(31)	−152.1
C(15)—O(11)—C(11)—C(14)	−173.3 (5)	N(21)—C(21)—C(23)—H(12)	−178.6
C(11)—O(11)—C(15)—O(12)	−8.6 (9)	N(21)—C(21)—C(23)—H(13)	−58.1
C(11)—O(11)—C(15)—N(21)	174.2 (4)	N(21)—C(21)—C(23)—H(14)	63.0
C(41)—O(41)—C(32)—O(31)	−4.4 (7)	C(22)—C(21)—C(23)—H(12)	55.9
C(32)—O(41)—C(41)—C(43)	164.0 (4)	C(22)—C(21)—C(23)—H(13)	176.5
C(21)—N(21)—C(15)—O(12)	−1.3 (8)	C(22)—C(21)—C(23)—H(14)	−62.4
C(15)—N(21)—C(21)—C(23)	161.9 (5)	H(11)—C(21)—C(23)—H(12)	−62.0
C(31)—N(31)—C(22)—O(21)	1.1 (10)	H(11)—C(21)—C(23)—H(13)	58.6
C(22)—N(31)—C(31)—C(33)	139.3 (5)	H(11)—C(21)—C(23)—H(14)	179.7
N(21)—C(21)—C(22)—O(21)	154.3 (6)	H(16)—C(31)—C(32)—O(31)	−162.8
C(23)—C(21)—C(22)—O(21)	−82.8 (7)	H(16)—C(31)—C(32)—O(41)	21.7
C(23)—C(21)—C(22)—N(31)	90.2 (7)	N(31)—C(31)—C(33)—H(17)	63.9
N(31)—C(31)—C(32)—O(31)	−42.5 (8)	N(31)—C(31)—C(33)—H(18)	−178.7
C(33)—C(31)—C(32)—O(31)	78.9 (7)	C(32)—C(31)—C(33)—H(17)	−57.5
C(33)—C(31)—C(32)—O(41)	−96.6 (5)	C(32)—C(31)—C(33)—H(18)	60.0
N(31)—C(31)—C(33)—C(34)	−57.0 (7)	H(16)—C(31)—C(33)—C(34)	62.3
C(32)—C(31)—C(33)—C(34)	−178.3 (5)	H(16)—C(31)—C(33)—H(17)	−176.8
C(31)—C(33)—C(34)—C(35)	−59.4 (6)	H(16)—C(31)—C(33)—H(18)	−59.3
C(31)—C(33)—C(34)—C(36)	178.3 (5)	C(31)—C(33)—C(34)—H(19)	60.2
O(41)—C(41)—C(42)—O(42)	154.5 (6)	H(17)—C(33)—C(34)—C(35)	−178.6
C(43)—C(41)—C(42)—O(42)	−87.7 (7)	H(17)—C(33)—C(34)—C(36)	59.1
C(43)—C(41)—C(42)—O(43)	94.0 (6)	H(17)—C(33)—C(34)—H(19)	−59.0
C(32)—O(41)—C(41)—H(26)	46.2	H(18)—C(33)—C(34)—C(35)	62.8
H(30)—O(43)—C(42)—O(42)	−9.7	H(18)—C(33)—C(34)—C(36)	−59.6
H(30)—O(43)—C(42)—C(41)	168.5	H(18)—C(33)—C(34)—H(19)	−177.6
H(10)—N(21)—C(15)—O(11)	−4.0	C(33)—C(34)—C(35)—H(20)	−61.2
H(10)—N(21)—C(15)—O(12)	178.6	C(33)—C(34)—C(35)—H(21)	58.2
C(15)—N(21)—C(21)—H(11)	44.6	C(33)—C(34)—C(35)—H(22)	178.2
H(10)—N(21)—C(21)—C(22)	104.4	C(36)—C(34)—C(35)—H(20)	60.1
H(10)—N(21)—C(21)—C(23)	−18.0	C(36)—C(34)—C(35)—H(21)	179.5
H(10)—N(21)—C(21)—H(11)	−135.3	C(36)—C(34)—C(35)—H(22)	−60.4
H(15)—N(31)—C(22)—O(21)	−177.9	H(19)—C(34)—C(35)—H(20)	179.6
H(15)—N(31)—C(22)—C(21)	9.2	H(19)—C(34)—C(35)—H(21)	−61.0
C(22)—N(31)—C(31)—H(16)	19.8	H(19)—C(34)—C(35)—H(22)	59.0
H(15)—N(31)—C(31)—C(32)	77.4	C(33)—C(34)—C(36)—H(23)	−177.4
H(15)—N(31)—C(31)—C(33)	−41.7	C(33)—C(34)—C(36)—H(24)	−57.7
H(15)—N(31)—C(31)—H(16)	−161.2	C(33)—C(34)—C(36)—H(25)	62.2
O(11)—C(11)—C(12)—H(1)	58.7	C(35)—C(34)—C(36)—H(23)	59.1
O(11)—C(11)—C(12)—H(2)	179.6	C(35)—C(34)—C(36)—H(24)	178.8
O(11)—C(11)—C(12)—H(3)	−60.3	C(35)—C(34)—C(36)—H(25)	−61.3
C(13)—C(11)—C(12)—H(1)	−65.4	H(19)—C(34)—C(36)—H(23)	−60.1
C(13)—C(11)—C(12)—H(2)	55.4	H(19)—C(34)—C(36)—H(24)	59.6
C(13)—C(11)—C(12)—H(3)	175.5	H(19)—C(34)—C(36)—H(25)	179.5
C(14)—C(11)—C(12)—H(1)	172.6	H(26)—C(41)—C(42)—O(42)	32.7
C(14)—C(11)—C(12)—H(2)	−66.6	H(26)—C(41)—C(42)—O(43)	−145.6
C(14)—C(11)—C(12)—H(3)	53.5	O(41)—C(41)—C(43)—H(27)	61.4
O(11)—C(11)—C(13)—H(4)	60.7	O(41)—C(41)—C(43)—H(28)	−179.4
O(11)—C(11)—C(13)—H(5)	−179.4	O(41)—C(41)—C(43)—H(29)	−58.4
O(11)—C(11)—C(13)—H(6)	−58.7	C(42)—C(41)—C(43)—H(27)	−59.9
C(12)—C(11)—C(13)—H(4)	−175.6	C(42)—C(41)—C(43)—H(28)	59.3
C(12)—C(11)—C(13)—H(5)	−55.7	C(42)—C(41)—C(43)—H(29)	−179.7
C(12)—C(11)—C(13)—H(6)	65.0	H(26)—C(41)—C(43)—H(27)	179.7
C(14)—C(11)—C(13)—H(4)	−54.9	H(26)—C(41)—C(43)—H(28)	−61.1
C(14)—C(11)—C(13)—H(5)	65.1	H(26)—C(41)—C(43)—H(29)	60.0
C(14)—C(11)—C(13)—H(6)	−174.3

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N21—H10···O42ⁱ	0.95	2.60	3.015 (6)	107
N31—H15···O42ⁱ	0.95	1.96	2.896 (7)	170
O43—H30···O21ⁱⁱ	0.90	1.72	2.590 (6)	161

Symmetry codes: (i) −x+2, y−1/2, −z; (ii) x+1, y, z.

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An N-protected depsipeptide free acid prepared by direct synthesis without using a terminal-C protecting group: tert-butoxy­carbonyl-L-alanyl-L-leucyl-L-lactic acid (Boc-L-Ala-L-Leu-L-Lac-OH)

Supporting information

Key indicators

checkCIF/PLATON results

An N-protected depsipeptide free acid prepared by direct synthesis without using a terminal-C protecting group: tert-butoxycarbonyl-L-alanyl-L-leucyl-L-lactic acid (Boc-L-Ala-L-Leu-L-Lac-OH)