Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
In the title compound, C4H10NO3+·C4H3O4, the threonine mol­ecule exists as a cation and the maleic acid mol­ecule exists in the mono-ionized state. In the semi-maleate ion, there is an intramolecular O—H...O hydrogen bond. The mol­ecules aggregate into infinite parallel layers which extend in the (0\overline 22) plane. These layers have no hydrogen-bonded interactions between them, only van der Waals interactions. The semi-maleate ion is essentially planar. The structure is stabilized by O—H...O and N—H...O hydrogen bonds, in addition to weak C—H...O interactions. No classical head-to-tail hydrogen bonds are observed.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804003277/ci6339sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804003277/ci6339Isup2.hkl
Contains datablock I

CCDC reference: 236084

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.001 Å
  • R factor = 0.034
  • wR factor = 0.093
  • Data-to-parameter ratio = 12.7

checkCIF/PLATON results

No syntax errors found


No errors found in this datablock

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97.

DL-Threoninium maleate top
Crystal data top
C4H10NO3+·C4H3O4Z = 2
Mr = 235.19F(000) = 248
Triclinic, P1Dx = 1.563 Mg m3
Dm = 1.57 Mg m3
Dm measured by flotation in a mixture of xylene and bromoform
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.8050 (12) ÅCell parameters from 1024 reflections
b = 8.4310 (17) Åθ = 2.0–28.3°
c = 10.740 (2) ŵ = 0.14 mm1
α = 98.88 (3)°T = 150 K
β = 105.17 (3)°Prismatic, colorless
γ = 91.68 (3)°0.5 × 0.5 × 0.3 mm
V = 499.90 (19) Å3
Data collection top
Bruker/SMART
diffractometer
2366 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.028
Graphite monochromatorθmax = 28.4°, θmin = 2.0°
Detector resolution: 8 pixels mm-1h = 77
ω scansk = 1111
7459 measured reflectionsl = 1414
2468 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.093 w = 1/[σ2(Fo2) + (0.0507P)2 + 0.1504P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max < 0.001
2468 reflectionsΔρmax = 0.42 e Å3
195 parametersΔρmin = 0.32 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.061 (9)
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
xyzUiso*/Ueq
O10.59462 (13)1.10303 (9)0.39309 (7)0.02098 (18)
H10.751 (4)1.133 (2)0.4185 (19)0.044 (5)*
O20.71631 (13)0.91813 (9)0.25623 (7)0.02208 (18)
O30.26663 (13)0.91897 (8)0.00676 (7)0.01706 (17)
H3O0.356 (3)0.871 (2)0.0395 (18)0.035 (4)*
O40.50780 (13)0.27172 (9)0.15272 (7)0.02067 (18)
O50.86638 (13)0.39959 (9)0.23023 (7)0.02148 (18)
H50.93190.48000.28630.032*
O61.05186 (13)0.62906 (9)0.39118 (7)0.02034 (18)
O70.95305 (13)0.80330 (9)0.53993 (7)0.02113 (18)
N10.15812 (15)1.08093 (10)0.21839 (8)0.01611 (18)
H1N0.244 (3)1.1560 (19)0.1922 (15)0.027 (4)*
H2N0.021 (3)1.061 (2)0.1603 (17)0.033 (4)*
H3N0.135 (3)1.1270 (19)0.2970 (17)0.030 (4)*
C10.55898 (17)0.98338 (11)0.29452 (9)0.0162 (2)
C20.29267 (16)0.93239 (11)0.23408 (9)0.01524 (19)
H20.234 (3)0.8798 (18)0.2947 (15)0.023 (3)*
C30.24743 (17)0.82100 (11)0.10294 (9)0.0161 (2)
H30.376 (2)0.7448 (16)0.1142 (13)0.018 (3)*
C40.00459 (19)0.72765 (12)0.06432 (10)0.0198 (2)
H4A0.005 (3)0.6600 (19)0.1290 (16)0.029 (4)*
H4B0.122 (3)0.7986 (18)0.0552 (14)0.022 (3)*
H4C0.018 (3)0.6581 (18)0.0187 (15)0.025 (3)*
C50.64327 (17)0.38206 (11)0.22697 (9)0.0164 (2)
C60.53977 (17)0.49631 (12)0.31459 (10)0.0179 (2)
H60.372 (3)0.4733 (18)0.3039 (14)0.023 (3)*
C70.64343 (17)0.62212 (12)0.40533 (9)0.0172 (2)
H70.548 (3)0.6800 (18)0.4528 (15)0.024 (3)*
C80.89873 (17)0.68859 (11)0.44769 (9)0.0160 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0162 (3)0.0267 (4)0.0162 (3)0.0016 (3)0.0036 (3)0.0062 (3)
O20.0181 (3)0.0251 (4)0.0217 (4)0.0020 (3)0.0065 (3)0.0024 (3)
O30.0205 (3)0.0186 (3)0.0133 (3)0.0001 (3)0.0082 (3)0.0003 (2)
O40.0215 (4)0.0203 (4)0.0188 (4)0.0039 (3)0.0078 (3)0.0042 (3)
O50.0181 (3)0.0220 (4)0.0230 (4)0.0024 (3)0.0098 (3)0.0067 (3)
O60.0151 (3)0.0246 (4)0.0195 (3)0.0010 (3)0.0064 (3)0.0043 (3)
O70.0190 (3)0.0256 (4)0.0156 (3)0.0026 (3)0.0049 (3)0.0058 (3)
N10.0145 (4)0.0184 (4)0.0140 (4)0.0004 (3)0.0046 (3)0.0025 (3)
C10.0172 (4)0.0187 (4)0.0121 (4)0.0003 (3)0.0039 (3)0.0015 (3)
C20.0160 (4)0.0169 (4)0.0124 (4)0.0008 (3)0.0049 (3)0.0003 (3)
C30.0190 (4)0.0155 (4)0.0130 (4)0.0005 (3)0.0053 (3)0.0006 (3)
C40.0231 (5)0.0184 (4)0.0164 (4)0.0054 (4)0.0057 (4)0.0012 (3)
C50.0191 (4)0.0165 (4)0.0145 (4)0.0001 (3)0.0065 (3)0.0015 (3)
C60.0150 (4)0.0199 (4)0.0188 (4)0.0001 (3)0.0066 (3)0.0008 (4)
C70.0155 (4)0.0199 (4)0.0167 (4)0.0012 (3)0.0070 (3)0.0003 (3)
C80.0158 (4)0.0191 (4)0.0124 (4)0.0002 (3)0.0035 (3)0.0014 (3)
Geometric parameters (Å, º) top
O1—C11.3133 (12)C1—C21.5316 (14)
O1—H10.89 (2)C2—C31.5226 (13)
O2—C11.2091 (13)C2—H20.965 (15)
O3—C31.4421 (12)C3—C41.5189 (14)
O3—H3O0.874 (19)C3—H30.992 (14)
O4—C51.2327 (13)C4—H4A0.975 (16)
O5—C51.2899 (12)C4—H4B0.956 (15)
O5—H50.8400C4—H4C0.964 (16)
O6—C81.2747 (12)C5—C61.4914 (14)
O7—C81.2406 (13)C6—C71.3317 (14)
N1—C21.5035 (13)C6—H60.962 (15)
N1—H1N0.916 (16)C7—C81.4957 (14)
N1—H2N0.866 (19)C7—H70.946 (16)
N1—H3N0.919 (17)
C1—O1—H1107.3 (12)O3—C3—H3110.8 (8)
C3—O3—H3O107.7 (11)C4—C3—H3109.5 (8)
C5—O5—H5109.5C2—C3—H3105.9 (8)
C2—N1—H1N110.5 (10)C3—C4—H4A110.3 (9)
C2—N1—H2N112.4 (11)C3—C4—H4B111.2 (9)
H1N—N1—H2N107.1 (14)H4A—C4—H4B110.1 (13)
C2—N1—H3N110.2 (10)C3—C4—H4C110.1 (9)
H1N—N1—H3N107.2 (14)H4A—C4—H4C107.7 (13)
H2N—N1—H3N109.3 (15)H4B—C4—H4C107.5 (12)
O2—C1—O1124.61 (9)O4—C5—O5122.08 (9)
O2—C1—C2123.26 (9)O4—C5—C6117.40 (9)
O1—C1—C2112.13 (9)O5—C5—C6120.52 (9)
N1—C2—C3110.38 (8)C7—C6—C5130.31 (9)
N1—C2—C1108.71 (8)C7—C6—H6115.7 (9)
C3—C2—C1112.07 (8)C5—C6—H6114.0 (9)
N1—C2—H2106.8 (9)C6—C7—C8129.43 (9)
C3—C2—H2110.2 (9)C6—C7—H7118.1 (9)
C1—C2—H2108.6 (9)C8—C7—H7112.4 (9)
O3—C3—C4110.96 (8)O7—C8—O6122.08 (9)
O3—C3—C2107.47 (7)O7—C8—C7116.83 (9)
C4—C3—C2112.08 (8)O6—C8—C7121.09 (9)
O2—C1—C2—N1136.12 (10)C1—C2—C3—C4161.21 (8)
O1—C1—C2—N145.02 (10)O4—C5—C6—C7178.22 (10)
O2—C1—C2—C313.84 (13)O5—C5—C6—C71.63 (17)
O1—C1—C2—C3167.29 (8)C5—C6—C7—C80.11 (19)
N1—C2—C3—O344.71 (10)C6—C7—C8—O7176.44 (10)
C1—C2—C3—O376.62 (10)C6—C7—C8—O63.42 (16)
N1—C2—C3—C477.46 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O7i0.89 (2)1.70 (2)2.598 (1)177 (2)
O3—H3O···O4ii0.87 (2)1.91 (2)2.771 (1)166 (2)
O5—H5···O60.841.562.400 (1)180
N1—H1N···O4iii0.92 (2)1.96 (2)2.848 (1)162 (1)
N1—H2N···O3iv0.87 (2)2.14 (2)2.968 (1)160 (2)
N1—H3N···O7v0.92 (2)1.96 (2)2.870 (1)171 (2)
C6—H6···O6vi0.96 (2)2.59 (2)3.328 (2)133 (1)
C7—H7···O1v0.95 (2)2.58 (2)3.489 (2)162 (1)
Symmetry codes: (i) x+2, y+2, z+1; (ii) x+1, y+1, z; (iii) x, y+1, z; (iv) x, y+2, z; (v) x+1, y+2, z+1; (vi) x1, y, z.
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds