Boc-AzAla-Ala-OMe.

THE TITLE COMPOUND (SYSTEMATIC NAME: tert-butyl 3-{[1-(methoxy-carbon-yl)eth-yl]amino-carbon-yl}-3-methyl-carbazate), C(11)H(21)N(3)O(5), is a precursor for the study of a new class of foldamer based on aza/α-dipeptide oligomerization [Abbas et al. (2009 ▶). Tetra-hedron Lett.50, 4158-4160]. The asymmetric unit consists of one mol-ecule in an extended conformation which is stabilized by inter-molecular N-H⋯O and C-H⋯O hydrogen bonding.

Related literature

For the synthesis, see: Majer & Randad (1994 ▶); Brosse et al. (2001 ▶); Bouillon et al. (2004 ▶); Abbas et al. (2009 ▶). For the geometry of the aza-residue in n class="Chemical">aza­peptides, see: Benatalah et al. (1991 ▶), André et al. (1996 ▶). For Boc-AzAla-Pro-NHiPr, see: André et al. (1997 ▶). For the refinement procedure, see: Flack & Schwarzenbach (1988 ▶). For hydrogen-bond motifs, see: Etter (1990 ▶).

Experimental

Crystal data

C11H21N3O5

M = 275.31

Tetragonal,

a = 9.3194 (4) Å

c = 17.4420 (8) Å

V = 1514.86 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.3 × 0.2 × 0.2 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: none

14534 measured reflections

1847 independent reflections

1806 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.076

S = 1.12

1847 reflections

178 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.13 e Å−3

Data collection: COLLECT (Bruker, 2004 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809045498/dn2501sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045498/dn2501Isup2.hkl

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

C11H21N3O5	Dx = 1.207 Mg m−3
Mr = 275.31	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P41	Cell parameters from 14534 reflections
Hall symbol: P 4w	θ = 2.5–27.9°
a = 9.3194 (4) Å	µ = 0.10 mm−1
c = 17.4420 (8) Å	T = 100 K
V = 1514.86 (12) Å3	Prism, colorless
Z = 4	0.3 × 0.2 × 0.2 mm
F(000) = 592

Nonis KappaCCD diffractometer	Rint = 0.049
CCD rotation images, thick slices scans	θmax = 27.8°, θmin = 2.5°
14534 measured reflections	h = −12→12
1847 independent reflections	k = −12→12
1806 reflections with I > 2σ(I)	l = −22→22

Refinement on F2	1 restraint
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.036	w = 1/[σ2(Fo2) + (0.0164P)2 + 0.7016P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.076	(Δ/σ)max < 0.001
S = 1.12	Δρmax = 0.17 e Å−3
1847 reflections	Δρmin = −0.13 e Å−3
178 parameters

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.

	x	y	z	Uiso*/Ueq
C1	0.3488 (2)	0.0563 (2)	0.63461 (13)	0.0228 (4)
C2	0.2822 (3)	−0.0204 (3)	0.56621 (14)	0.0311 (5)
H2A	0.1902	0.021	0.5551	0.047*
H2B	0.2706	−0.1204	0.578	0.047*
H2C	0.3438	−0.0103	0.5224	0.047*
C3	0.2529 (3)	0.0415 (2)	0.70463 (14)	0.0279 (5)
H3A	0.2995	0.0837	0.7482	0.042*
H3B	0.235	−0.0582	0.7145	0.042*
H3C	0.1635	0.0898	0.6954	0.042*
C4	0.5016 (3)	0.0058 (3)	0.64752 (15)	0.0308 (5)
H4A	0.557	0.022	0.6019	0.046*
H4B	0.5015	−0.0948	0.6594	0.046*
H4C	0.5431	0.0583	0.6894	0.046*
O1	0.35134 (16)	0.20833 (15)	0.60837 (9)	0.0218 (3)
C5	0.3987 (2)	0.3109 (2)	0.65626 (12)	0.0193 (4)
O2	0.43957 (17)	0.29435 (17)	0.72181 (9)	0.0239 (3)
N1	0.39666 (19)	0.44041 (18)	0.61993 (11)	0.0201 (4)
H1	0.3753	0.4464	0.5721	0.024*
N2	0.43006 (19)	0.56280 (19)	0.66214 (11)	0.0200 (4)
C6	0.3156 (2)	0.6117 (2)	0.71325 (14)	0.0259 (5)
H6A	0.2304	0.63	0.6839	0.039*
H6B	0.3451	0.6982	0.7386	0.039*
H6C	0.2961	0.5389	0.7508	0.039*
C7	0.5716 (2)	0.5760 (2)	0.68660 (12)	0.0189 (4)
O3	0.60321 (16)	0.65021 (16)	0.74280 (8)	0.0221 (3)
N3	0.67193 (19)	0.50835 (19)	0.64451 (10)	0.0209 (4)
H3	0.6487	0.4606	0.6042	0.025*
C8	0.8201 (2)	0.5181 (2)	0.66902 (13)	0.0232 (4)
H8	0.8264	0.478	0.7209	0.028*
C9	0.9146 (2)	0.4274 (3)	0.61671 (14)	0.0296 (5)
H9A	0.8853	0.3288	0.6198	0.044*
H9B	1.0129	0.4358	0.6326	0.044*
H9C	0.9052	0.4605	0.5648	0.044*
C10	0.8773 (2)	0.6709 (3)	0.67187 (13)	0.0244 (4)
O4	0.97394 (18)	0.7060 (2)	0.71417 (11)	0.0333 (4)
O5	0.81613 (16)	0.75824 (17)	0.62089 (9)	0.0249 (3)
C11	0.8685 (3)	0.9048 (3)	0.62253 (16)	0.0310 (5)
H11A	0.8424	0.9487	0.6703	0.046*
H11B	0.8267	0.9578	0.581	0.046*
H11C	0.971	0.9048	0.6174	0.046*

	U11	U22	U33	U12	U13	U23
C1	0.0313 (11)	0.0171 (9)	0.0199 (10)	−0.0034 (8)	0.0039 (9)	0.0017 (8)
C2	0.0429 (14)	0.0269 (12)	0.0236 (11)	−0.0138 (10)	0.0058 (10)	−0.0039 (9)
C3	0.0345 (12)	0.0232 (10)	0.0261 (11)	−0.0033 (9)	0.0091 (10)	−0.0012 (9)
C4	0.0339 (11)	0.0269 (11)	0.0317 (12)	0.0044 (9)	0.0059 (10)	0.0039 (10)
O1	0.0288 (8)	0.0190 (7)	0.0178 (7)	−0.0036 (6)	−0.0026 (6)	0.0000 (6)
C5	0.0183 (9)	0.0217 (10)	0.0180 (10)	−0.0021 (7)	0.0011 (8)	−0.0017 (8)
O2	0.0304 (8)	0.0240 (8)	0.0172 (7)	−0.0031 (6)	−0.0033 (6)	0.0007 (6)
N1	0.0251 (9)	0.0199 (8)	0.0155 (8)	−0.0020 (7)	−0.0033 (7)	−0.0001 (7)
N2	0.0217 (8)	0.0204 (8)	0.0178 (8)	−0.0010 (6)	0.0005 (7)	−0.0014 (7)
C6	0.0224 (10)	0.0256 (11)	0.0295 (12)	0.0017 (8)	0.0029 (9)	−0.0037 (9)
C7	0.0213 (10)	0.0190 (9)	0.0164 (10)	−0.0028 (8)	0.0009 (7)	0.0023 (8)
O3	0.0240 (8)	0.0256 (8)	0.0165 (7)	−0.0023 (6)	0.0026 (6)	−0.0024 (6)
N3	0.0197 (8)	0.0273 (9)	0.0157 (8)	−0.0014 (7)	0.0003 (7)	−0.0035 (7)
C8	0.0212 (10)	0.0306 (11)	0.0179 (10)	0.0013 (8)	−0.0020 (8)	0.0005 (9)
C9	0.0231 (11)	0.0413 (13)	0.0243 (11)	0.0049 (9)	0.0008 (9)	−0.0043 (10)
C10	0.0186 (10)	0.0357 (12)	0.0188 (10)	0.0012 (9)	0.0007 (8)	−0.0009 (9)
O4	0.0263 (8)	0.0421 (10)	0.0316 (9)	−0.0027 (7)	−0.0105 (7)	−0.0012 (8)
O5	0.0228 (8)	0.0301 (8)	0.0217 (8)	−0.0039 (6)	−0.0038 (6)	0.0018 (7)
C11	0.0283 (12)	0.0330 (12)	0.0317 (12)	−0.0052 (9)	−0.0019 (10)	0.0031 (10)

C1—O1	1.489 (2)	C6—H6A	0.96
C1—C4	1.517 (3)	C6—H6B	0.96
C1—C3	1.520 (3)	C6—H6C	0.96
C1—C2	1.523 (3)	C7—O3	1.235 (3)
C2—H2A	0.96	C7—N3	1.346 (3)
C2—H2B	0.96	N3—C8	1.448 (3)
C2—H2C	0.96	N3—H3	0.86
C3—H3A	0.96	C8—C10	1.521 (3)
C3—H3B	0.96	C8—C9	1.524 (3)
C3—H3C	0.96	C8—H8	0.98
C4—H4A	0.96	C9—H9A	0.96
C4—H4B	0.96	C9—H9B	0.96
C4—H4C	0.96	C9—H9C	0.96
O1—C5	1.344 (2)	C10—O4	1.210 (3)
C5—O2	1.215 (3)	C10—O5	1.334 (3)
C5—N1	1.363 (3)	O5—C11	1.450 (3)
N1—N2	1.393 (2)	C11—H11A	0.96
N1—H1	0.86	C11—H11B	0.96
N2—C7	1.392 (3)	C11—H11C	0.96
N2—C6	1.463 (3)
O1—C1—C4	109.01 (17)	N2—C6—H6A	109.5
O1—C1—C3	110.01 (17)	N2—C6—H6B	109.5
C4—C1—C3	113.9 (2)	H6A—C6—H6B	109.5
O1—C1—C2	102.26 (17)	N2—C6—H6C	109.5
C4—C1—C2	110.7 (2)	H6A—C6—H6C	109.5
C3—C1—C2	110.32 (19)	H6B—C6—H6C	109.5
C1—C2—H2A	109.5	O3—C7—N3	122.0 (2)
C1—C2—H2B	109.5	O3—C7—N2	121.24 (19)
H2A—C2—H2B	109.5	N3—C7—N2	116.72 (18)
C1—C2—H2C	109.5	C7—N3—C8	118.14 (18)
H2A—C2—H2C	109.5	C7—N3—H3	120.9
H2B—C2—H2C	109.5	C8—N3—H3	120.9
C1—C3—H3A	109.5	N3—C8—C10	113.75 (18)
C1—C3—H3B	109.5	N3—C8—C9	109.84 (18)
H3A—C3—H3B	109.5	C10—C8—C9	109.64 (19)
C1—C3—H3C	109.5	N3—C8—H8	107.8
H3A—C3—H3C	109.5	C10—C8—H8	107.8
H3B—C3—H3C	109.5	C9—C8—H8	107.8
C1—C4—H4A	109.5	C8—C9—H9A	109.5
C1—C4—H4B	109.5	C8—C9—H9B	109.5
H4A—C4—H4B	109.5	H9A—C9—H9B	109.5
C1—C4—H4C	109.5	C8—C9—H9C	109.5
H4A—C4—H4C	109.5	H9A—C9—H9C	109.5
H4B—C4—H4C	109.5	H9B—C9—H9C	109.5
C5—O1—C1	119.40 (17)	O4—C10—O5	124.0 (2)
O2—C5—O1	126.7 (2)	O4—C10—C8	122.3 (2)
O2—C5—N1	123.66 (19)	O5—C10—C8	113.58 (18)
O1—C5—N1	109.64 (18)	C10—O5—C11	114.71 (18)
C5—N1—N2	118.43 (18)	O5—C11—H11A	109.5
C5—N1—H1	120.8	O5—C11—H11B	109.5
N2—N1—H1	120.8	H11A—C11—H11B	109.5
C7—N2—N1	116.51 (17)	O5—C11—H11C	109.5
C7—N2—C6	118.49 (18)	H11A—C11—H11C	109.5
N1—N2—C6	114.46 (17)	H11B—C11—H11C	109.5
C4—C1—O1—C5	−65.6 (2)	C6—N2—C7—N3	168.95 (18)
C3—C1—O1—C5	60.0 (2)	O3—C7—N3—C8	3.2 (3)
C2—C1—O1—C5	177.16 (18)	N2—C7—N3—C8	−179.09 (18)
C1—O1—C5—O2	−1.3 (3)	C7—N3—C8—C10	−60.0 (3)
C1—O1—C5—N1	177.86 (17)	C7—N3—C8—C9	176.65 (19)
O2—C5—N1—N2	−6.4 (3)	N3—C8—C10—O4	153.4 (2)
O1—C5—N1—N2	174.45 (17)	C9—C8—C10—O4	−83.2 (3)
C5—N1—N2—C7	68.4 (2)	N3—C8—C10—O5	−30.0 (3)
C5—N1—N2—C6	−75.9 (2)	C9—C8—C10—O5	93.5 (2)
N1—N2—C7—O3	−156.14 (19)	O4—C10—O5—C11	−3.6 (3)
C6—N2—C7—O3	−13.3 (3)	C8—C10—O5—C11	179.84 (19)
N1—N2—C7—N3	26.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.86	2.18	2.972 (2)	153
N3—H3···O3i	0.86	2.03	2.850 (2)	159
C6—H6A···O4ii	0.96	2.55	3.303 (3)	136
C11—H11B···O4iii	0.96	2.41	3.346 (3)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.86	2.18	2.972 (2)	153
N3—H3⋯O3i	0.86	2.03	2.850 (2)	159
C6—H6A⋯O4ii	0.96	2.55	3.303 (3)	136
C11—H11B⋯O4iii	0.96	2.41	3.346 (3)	164

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