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In the title compound, C7H14N2O4, peptide mol­ecules are connected into β-sheet-like ribbons along the short tetra­gonal axis [4.7065 (4) Å] by one N—H...O and two Cα;—H...O inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805017174/hg6197sup1.cif
Contains datablocks TA, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805017174/hg6197TAsup2.hkl
Contains datablock TA

CCDC reference: 277274

Key indicators

  • Single-crystal X-ray study
  • T = 105 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.029
  • wR factor = 0.074
  • Data-to-parameter ratio = 8.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.00 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.87 Ratio
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 27.85 From the CIF: _reflns_number_total 1207 Count of symmetry unique reflns 1216 Completeness (_total/calc) 99.26% 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
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 1 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Bruker, 2000); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

L-threonyl-L-alanine top
Crystal data top
C7H14N2O4Dx = 1.387 Mg m3
Mr = 190.20Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P42Cell parameters from 3024 reflections
Hall symbol: P 4cθ = 2.1–27.9°
a = 13.9136 (7) ŵ = 0.11 mm1
c = 4.7065 (4) ÅT = 105 K
V = 911.12 (10) Å3Needle, colourless
Z = 40.45 × 0.05 × 0.05 mm
F(000) = 408
Data collection top
Siemens SMART CCD
diffractometer
1207 independent reflections
Radiation source: fine-focus sealed tube1097 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
Detector resolution: 8.3 pixels mm-1θmax = 27.9°, θmin = 2.1°
ω scansh = 1018
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1716
Tmin = 0.905, Tmax = 0.994l = 66
6059 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.074H atoms treated by a mixture of independent and constrained refinement
S = 1.09 w = 1/[σ2(Fo2) + (0.0409P)2 + 0.119P]
where P = (Fo2 + 2Fc2)/3
1207 reflections(Δ/σ)max = 0.002
138 parametersΔρmax = 0.22 e Å3
2 restraintsΔρmin = 0.17 e Å3
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. Data were collected by measuring three sets of exposures with the detector set at 2θ = 29°, crystal-to-detector distance 5.00 cm. Refinement of F2 against ALL reflections.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.28513 (10)0.80250 (11)1.0257 (3)0.0271 (3)
O20.54581 (9)0.74841 (9)0.5354 (3)0.0212 (3)
H50.5802 (17)0.7842 (18)0.637 (6)0.032*
O30.11041 (8)0.62550 (8)0.3569 (3)0.0189 (3)
O40.00409 (9)0.62187 (10)0.7115 (3)0.0250 (3)
N10.42505 (10)0.90436 (10)0.7087 (4)0.0143 (3)
H10.4058 (15)0.9506 (16)0.583 (6)0.021*
H20.4919 (15)0.9029 (14)0.702 (5)0.021*
H30.4053 (16)0.9215 (15)0.881 (6)0.021*
N20.21644 (11)0.76639 (11)0.6040 (4)0.0159 (3)
H40.2248 (15)0.7631 (15)0.432 (5)0.019*
C10.38596 (12)0.80918 (12)0.6153 (4)0.0128 (3)
H110.3745 (14)0.8108 (14)0.418 (6)0.015*
C20.45825 (11)0.72863 (11)0.6831 (4)0.0153 (3)
H210.47040.72600.89240.018*
C30.42047 (13)0.63251 (12)0.5800 (5)0.0225 (4)
H310.46940.58290.61020.034*
H320.40530.63680.37700.034*
H330.36220.61580.68610.034*
C40.29002 (12)0.79267 (12)0.7659 (4)0.0146 (4)
C50.12218 (12)0.74402 (12)0.7249 (4)0.0177 (4)
H510.13070.73100.93230.021*
C60.05392 (15)0.82982 (14)0.6925 (7)0.0384 (6)
H610.08060.88550.79250.058*
H620.00890.81350.77370.058*
H630.04640.84520.49060.058*
C70.07707 (11)0.65561 (12)0.5891 (4)0.0152 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0207 (7)0.0490 (9)0.0118 (6)0.0107 (6)0.0001 (6)0.0024 (7)
O20.0146 (6)0.0203 (7)0.0289 (8)0.0027 (4)0.0042 (6)0.0067 (6)
O30.0188 (6)0.0200 (6)0.0178 (7)0.0017 (4)0.0024 (6)0.0038 (6)
O40.0212 (6)0.0366 (7)0.0172 (6)0.0128 (5)0.0036 (6)0.0029 (6)
N10.0138 (7)0.0127 (7)0.0163 (8)0.0001 (5)0.0008 (6)0.0002 (7)
N20.0144 (7)0.0231 (7)0.0101 (6)0.0042 (5)0.0009 (6)0.0014 (6)
C10.0143 (8)0.0136 (8)0.0106 (8)0.0028 (6)0.0017 (7)0.0008 (7)
C20.0152 (8)0.0149 (8)0.0159 (8)0.0009 (6)0.0008 (7)0.0004 (7)
C30.0225 (9)0.0146 (8)0.0303 (11)0.0015 (6)0.0020 (9)0.0024 (8)
C40.0156 (8)0.0155 (8)0.0126 (9)0.0014 (6)0.0002 (7)0.0017 (7)
C50.0146 (8)0.0230 (9)0.0155 (8)0.0031 (6)0.0031 (7)0.0043 (8)
C60.0217 (9)0.0253 (10)0.0683 (18)0.0011 (8)0.0067 (11)0.0114 (13)
C70.0139 (7)0.0175 (8)0.0141 (8)0.0005 (6)0.0021 (7)0.0009 (7)
Geometric parameters (Å, º) top
O1—C41.232 (2)C1—C21.539 (2)
O2—C21.429 (2)C1—H110.94 (3)
O2—H50.84 (3)C2—C31.517 (2)
O3—C71.259 (2)C2—H211.0000
O4—C71.258 (2)C3—H310.9800
N1—C11.498 (2)C3—H320.9800
N1—H10.91 (2)C3—H330.9800
N1—H20.93 (2)C5—C71.522 (2)
N1—H30.89 (3)C5—C61.533 (3)
N2—C41.328 (2)C5—H511.0000
N2—C51.463 (2)C6—H610.9800
N2—H40.82 (2)C6—H620.9800
C1—C41.529 (2)C6—H630.9800
C2—O2—H5108.9 (18)C2—C3—H32109.5
C1—N1—H1109.0 (14)H31—C3—H32109.5
C1—N1—H2109.5 (13)C2—C3—H33109.5
H1—N1—H2106.6 (19)H31—C3—H33109.5
C1—N1—H3113.1 (14)H32—C3—H33109.5
H1—N1—H3108 (2)O1—C4—N2123.90 (17)
H2—N1—H3110 (2)O1—C4—C1119.45 (17)
C4—N2—C5121.78 (16)N2—C4—C1116.65 (16)
C4—N2—H4118.2 (15)N2—C5—C7112.24 (15)
C5—N2—H4120.0 (15)N2—C5—C6110.56 (16)
N1—C1—C4108.29 (14)C7—C5—C6109.41 (16)
N1—C1—C2110.22 (13)N2—C5—H51108.2
C4—C1—C2111.41 (14)C7—C5—H51108.2
N1—C1—H11109.2 (12)C6—C5—H51108.2
C4—C1—H11108.2 (12)C5—C6—H61109.5
C2—C1—H11109.4 (12)C5—C6—H62109.5
O2—C2—C3108.02 (14)H61—C6—H62109.5
O2—C2—C1108.41 (13)C5—C6—H63109.5
C3—C2—C1110.43 (14)H61—C6—H63109.5
O2—C2—H21110.0H62—C6—H63109.5
C3—C2—H21110.0O4—C7—O3124.79 (16)
C1—C2—H21110.0O4—C7—C5116.25 (16)
C2—C3—H31109.5O3—C7—C5118.78 (15)
N1—C1—C4—N2130.52 (16)C5—N2—C4—O11.7 (3)
C1—C4—N2—C5177.03 (15)N1—C1—C4—O150.7 (2)
C4—N2—C5—C7137.75 (17)C2—C1—C4—O170.7 (2)
N2—C5—C7—O316.2 (2)C2—C1—C4—N2108.11 (18)
N1—C1—C2—O259.93 (19)C4—N2—C5—C699.8 (2)
N1—C1—C2—C3178.09 (16)N2—C5—C7—O4168.46 (16)
C1—C2—O2—H587.2 (18)C6—C5—C7—O468.4 (2)
C4—C1—C2—O2179.82 (15)C6—C5—C7—O3107.0 (2)
C4—C1—C2—C361.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O4i0.91 (2)1.94 (3)2.798 (2)156 (2)
N1—H2···O3ii0.93 (2)2.01 (2)2.8822 (19)156 (2)
N1—H3···O4iii0.89 (3)1.97 (3)2.820 (2)159 (2)
N2—H4···O1iv0.82 (2)2.16 (2)2.928 (2)156 (2)
O2—H5···O3ii0.84 (3)1.90 (3)2.7163 (19)163 (2)
C1—H11···O1iv0.94 (3)2.23 (2)3.111 (2)155.4 (17)
C3—H33···O2v0.982.453.402 (3)163
C5—H51···O3vi1.002.503.405 (2)151
Symmetry codes: (i) y+1, x+1, z1/2; (ii) y, x+1, z+1/2; (iii) y+1, x+1, z+1/2; (iv) x, y, z1; (v) y+1, x, z+1/2; (vi) x, y, z+1.
 

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