l-Leucylglycylglycine.

In the title compound, C10H19N3O4, the N- and C-termini are protonated and ionized, respectively, and the mol-ecule forms a zwitterion. The main chain is in a folded form. In the crystal, the N-terminal -NH3 (+) group hydrogen bonds to three C-terminal -COO groups and one carbonyl O atom, forming a three-dimensional network. In addition, an N-H⋯O hydrogen bond between the amide groups of the middle glycine residue and a C-H⋯O inter-action continue along the a-axis direction. The side chains of the leucyl residues form a hydro-phobic region along the a axis.

Related literature

For related structures of l-leucylglycylglycine, see: Goswami et al. (1977 ▶); Srikrishnan & Parthasarathy (1987 ▶); Kiyotani & Sugawara (2012 ▶).

Experimental

Crystal data

C10H19N3O4

M = 245.28

Orthorhombic,

a = 5.391 (5) Å

b = 11.742 (10) Å

c = 19.975 (16) Å

V = 1264.4 (19) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 173 K

0.48 × 0.18 × 0.08 mm

Data collection

Rigaku Mercury CCD area-detecter diffractometer

9374 measured reflections

2887 independent reflections

2200 reflections with I > 2σ(I)

R int = 0.070

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.087

S = 0.96

2887 reflections

176 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.14 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CrystalClear (Rigaku, 2006 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008 ▶) and Yadokari-XG 2009 (Kabuto et al., 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813008490/is5257sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813008490/is5257Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813008490/is5257Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H19N3O4	F(000) = 528
Mr = 245.28	Dx = 1.288 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: P 2ac 2ab	Cell parameters from 949 reflections
a = 5.391 (5) Å	θ = 7.6–17.5°
b = 11.742 (10) Å	µ = 0.10 mm−1
c = 19.975 (16) Å	T = 173 K
V = 1264.4 (19) Å3	Block Rod, colorless
Z = 4	0.48 × 0.18 × 0.08 mm

Rigaku Mercury CCD area-detecter diffractometer	2200 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.070
Graphite monochromator	θmax = 27.5°, θmin = 3.5°
ω scans	h = −6→6
9374 measured reflections	k = −15→15
2887 independent reflections	l = −21→25

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ2(Fo2) + (0.0374P)2] where P = (Fo2 + 2Fc2)/3
2887 reflections	(Δ/σ)max = 0.012
176 parameters	Δρmax = 0.14 e Å−3
3 restraints	Δρmin = −0.17 e Å−3

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
N1	−0.1744 (3)	0.64554 (12)	0.49670 (7)	0.0348 (3)
N2	−0.0484 (3)	0.64749 (12)	0.67001 (6)	0.0315 (3)
H5	−0.195 (4)	0.6402 (15)	0.6825 (9)	0.036 (5)*
N3	0.1814 (3)	0.52895 (12)	0.78349 (7)	0.0362 (3)
H8	0.022 (4)	0.5354 (16)	0.7880 (9)	0.048 (6)*
O1	0.2239 (2)	0.64148 (11)	0.58454 (5)	0.0415 (3)
O2	0.5246 (2)	0.62376 (11)	0.75146 (6)	0.0485 (3)
C1	−0.1911 (3)	0.58011 (12)	0.56075 (8)	0.0290 (3)
H4	−0.3570	0.5921	0.5820	0.035*
C2	0.0137 (3)	0.62595 (12)	0.60611 (7)	0.0273 (3)
C3	0.1320 (3)	0.69772 (14)	0.71523 (8)	0.0368 (4)
H6	0.0422	0.7431	0.7493	0.044*
H7	0.2381	0.7507	0.6894	0.044*
C4	0.2975 (3)	0.61277 (13)	0.75092 (7)	0.0314 (4)
C5	0.3059 (3)	0.45098 (16)	0.82883 (9)	0.0406 (4)
H9	0.4550	0.4883	0.8477	0.049*
H10	0.3604	0.3826	0.8038	0.049*
C6	0.1333 (4)	0.41541 (13)	0.88559 (8)	0.0354 (4)
O3	0.2277 (3)	0.35522 (11)	0.93090 (6)	0.0536 (4)
O4	−0.0855 (3)	0.44525 (12)	0.88306 (7)	0.0545 (4)
C7	−0.1526 (3)	0.45349 (13)	0.54488 (8)	0.0374 (4)
H11	−0.2711	0.4312	0.5094	0.045*
H12	0.0168	0.4434	0.5267	0.045*
C8	−0.1855 (4)	0.37232 (14)	0.60441 (9)	0.0413 (4)
H13	−0.0679	0.3959	0.6406	0.050*
C9	−0.1199 (5)	0.25116 (15)	0.58278 (10)	0.0636 (7)
H14	−0.1379	0.1995	0.6210	0.076*
H15	0.0518	0.2492	0.5667	0.076*
H16	−0.2316	0.2272	0.5467	0.095*
C10	−0.4475 (5)	0.3769 (2)	0.63228 (13)	0.0715 (7)
H17	−0.5664	0.3609	0.5964	0.086*
H18	−0.4796	0.4529	0.6507	0.086*
H19	−0.4656	0.3199	0.6678	0.086*
H1	−0.011 (5)	0.636 (2)	0.4768 (12)	0.089 (9)*
H2	−0.284 (5)	0.6147 (19)	0.4666 (12)	0.076 (7)*
H3	−0.202 (4)	0.7193 (16)	0.5047 (11)	0.058 (6)*

	U11	U22	U33	U12	U13	U23
N1	0.0420 (9)	0.0301 (7)	0.0322 (7)	−0.0012 (7)	−0.0133 (7)	0.0028 (6)
N2	0.0312 (8)	0.0404 (8)	0.0228 (6)	−0.0052 (7)	0.0020 (6)	0.0025 (6)
N3	0.0288 (8)	0.0458 (8)	0.0341 (7)	−0.0020 (7)	0.0000 (6)	0.0152 (6)
O1	0.0248 (6)	0.0666 (8)	0.0332 (6)	−0.0019 (6)	0.0030 (5)	0.0004 (6)
O2	0.0387 (8)	0.0668 (9)	0.0399 (7)	−0.0099 (7)	0.0061 (5)	0.0128 (6)
C1	0.0284 (8)	0.0304 (7)	0.0282 (8)	0.0006 (7)	−0.0021 (7)	0.0001 (6)
C2	0.0272 (8)	0.0294 (8)	0.0253 (7)	0.0018 (7)	0.0018 (6)	0.0038 (6)
C3	0.0496 (12)	0.0340 (8)	0.0268 (8)	−0.0083 (8)	−0.0054 (8)	0.0034 (7)
C4	0.0375 (10)	0.0396 (9)	0.0172 (7)	−0.0051 (8)	0.0031 (7)	0.0006 (6)
C5	0.0365 (10)	0.0480 (10)	0.0373 (9)	0.0046 (9)	0.0010 (8)	0.0148 (8)
C6	0.0498 (11)	0.0301 (8)	0.0264 (8)	−0.0120 (8)	−0.0017 (8)	0.0028 (7)
O3	0.0698 (9)	0.0532 (7)	0.0379 (7)	−0.0196 (7)	−0.0195 (7)	0.0220 (6)
O4	0.0427 (8)	0.0644 (9)	0.0562 (8)	0.0010 (7)	0.0156 (7)	0.0178 (7)
C7	0.0482 (11)	0.0303 (8)	0.0338 (9)	0.0007 (8)	−0.0012 (8)	−0.0004 (7)
C8	0.0532 (11)	0.0325 (8)	0.0381 (9)	−0.0025 (9)	−0.0036 (8)	0.0037 (8)
C9	0.096 (2)	0.0342 (10)	0.0602 (14)	0.0078 (10)	0.0029 (13)	0.0088 (9)
C10	0.0713 (16)	0.0552 (13)	0.0882 (17)	−0.0017 (12)	0.0223 (13)	0.0234 (12)

N1—C1	1.495 (2)	C5—C6	1.525 (3)
N1—H1	0.97 (2)	C5—H9	0.9900
N1—H2	0.92 (2)	C5—H10	0.9900
N1—H3	0.894 (19)	C6—O4	1.232 (3)
N2—C2	1.344 (2)	C6—O3	1.256 (2)
N2—C3	1.452 (2)	C7—C8	1.534 (2)
N2—H5	0.83 (2)	C7—H11	0.9900
N3—C4	1.336 (2)	C7—H12	0.9900
N3—C5	1.452 (2)	C8—C10	1.519 (3)
N3—H8	0.87 (2)	C8—C9	1.528 (3)
O1—C2	1.226 (2)	C8—H13	1.0000
O2—C4	1.231 (2)	C9—H14	0.9800
C1—C2	1.526 (2)	C9—H15	0.9800
C1—C7	1.534 (2)	C9—H16	0.9800
C1—H4	1.0000	C10—H17	0.9800
C3—C4	1.516 (2)	C10—H18	0.9800
C3—H6	0.9900	C10—H19	0.9800
C3—H7	0.9900
C1—N1—H1	110.2 (15)	C6—C5—H9	109.5
C1—N1—H2	108.6 (14)	N3—C5—H10	109.5
H1—N1—H2	105 (2)	C6—C5—H10	109.5
C1—N1—H3	109.6 (14)	H9—C5—H10	108.1
H1—N1—H3	110 (2)	O4—C6—O3	125.31 (17)
H2—N1—H3	113 (2)	O4—C6—C5	118.43 (16)
C2—N2—C3	120.03 (15)	O3—C6—C5	116.25 (18)
C2—N2—H5	120.0 (13)	C8—C7—C1	115.23 (14)
C3—N2—H5	119.4 (13)	C8—C7—H11	108.5
C4—N3—C5	123.47 (17)	C1—C7—H11	108.5
C4—N3—H8	116.8 (13)	C8—C7—H12	108.5
C5—N3—H8	116.7 (13)	C1—C7—H12	108.5
N1—C1—C2	106.45 (13)	H11—C7—H12	107.5
N1—C1—C7	108.24 (13)	C10—C8—C9	110.59 (17)
C2—C1—C7	111.49 (13)	C10—C8—C7	111.68 (16)
N1—C1—H4	110.2	C9—C8—C7	109.41 (15)
C2—C1—H4	110.2	C10—C8—H13	108.4
C7—C1—H4	110.2	C9—C8—H13	108.4
O1—C2—N2	122.41 (14)	C7—C8—H13	108.4
O1—C2—C1	120.84 (14)	C8—C9—H14	109.5
N2—C2—C1	116.75 (14)	C8—C9—H15	109.5
N2—C3—C4	114.79 (14)	H14—C9—H15	109.5
N2—C3—H6	108.6	C8—C9—H16	109.5
C4—C3—H6	108.6	H14—C9—H16	109.5
N2—C3—H7	108.6	H15—C9—H16	109.5
C4—C3—H7	108.6	C8—C10—H17	109.5
H6—C3—H7	107.5	C8—C10—H18	109.5
O2—C4—N3	122.62 (16)	H17—C10—H18	109.5
O2—C4—C3	121.36 (15)	C8—C10—H19	109.5
N3—C4—C3	115.97 (17)	H17—C10—H19	109.5
N3—C5—C6	110.74 (16)	H18—C10—H19	109.5
N3—C5—H9	109.5
C3—N2—C2—O1	4.0 (2)	N2—C3—C4—O2	129.75 (17)
C3—N2—C2—C1	−176.27 (13)	N2—C3—C4—N3	−52.78 (19)
N1—C1—C2—O1	−45.43 (19)	C4—N3—C5—C6	147.06 (16)
C7—C1—C2—O1	72.41 (19)	N3—C5—C6—O4	7.0 (2)
N1—C1—C2—N2	134.83 (14)	N3—C5—C6—O3	−174.41 (14)
C7—C1—C2—N2	−107.33 (16)	N1—C1—C7—C8	−175.12 (14)
C2—N2—C3—C4	−87.54 (18)	C2—C1—C7—C8	68.14 (19)
C5—N3—C4—O2	7.5 (2)	C1—C7—C8—C10	62.1 (2)
C5—N3—C4—C3	−169.93 (15)	C1—C7—C8—C9	−175.13 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3i	0.97 (3)	1.78 (3)	2.743 (2)	168 (2)
N1—H2···O4ii	0.92 (2)	1.94 (2)	2.822 (2)	160 (2)
N1—H2···O3ii	0.92 (2)	2.52 (2)	3.260 (2)	138 (2)
N1—H3···O1iii	0.89 (2)	2.45 (2)	3.031 (2)	123 (2)
N1—H3···O3iv	0.89 (2)	2.05 (2)	2.870 (2)	151 (2)
N2—H5···O2v	0.83 (2)	2.05 (2)	2.832 (2)	155 (2)
C1—H4···O1v	1.00	2.33	3.269 (2)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3i	0.97 (3)	1.78 (3)	2.743 (2)	168 (2)
N1—H2⋯O4ii	0.92 (2)	1.94 (2)	2.822 (2)	160 (2)
N1—H2⋯O3ii	0.92 (2)	2.52 (2)	3.260 (2)	138 (2)
N1—H3⋯O1iii	0.89 (2)	2.45 (2)	3.031 (2)	123 (2)
N1—H3⋯O3iv	0.89 (2)	2.05 (2)	2.870 (2)	151 (2)
N2—H5⋯O2v	0.83 (2)	2.05 (2)	2.832 (2)	155 (2)
C1—H4⋯O1v	1.00	2.33	3.269 (2)	155

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .