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The title compound, C7H11NO5·H2O, a hydrated stereoisomer of the N-acetyl­ated lactone of polyoxamic acid, contains a lactone ring with an envelope conformation, all substituents being cis. Intermolecular hydrogen bonds involving all possible donors link the lactone mol­ecules into sheets, which are interlinked by the water mol­ecules to give a three-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803014120/bt6295sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803014120/bt6295Isup2.hkl
Contains datablock I

CCDC reference: 217619

Key indicators

  • Single-crystal X-ray study
  • T = 160 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.038
  • wR factor = 0.082
  • Data-to-parameter ratio = 9.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 28.36 From the CIF: _reflns_number_total 1352 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 1425 Completeness (_total/calc) 94.88% Alert C: < 95% complete General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 28.36 From the CIF: _reflns_number_total 1352 Count of symmetry unique reflns 1425 Completeness (_total/calc) 94.88% 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 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.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Comment top

The title lactone, (I), was prepared as part of a project concerned with the synthesis of β-hydroxy-α-amino acids via (arylthio)nitrooxiranes (Jackson et al., 1995). Its crystal structure has been determined in order to confirm the relative stereochemistry of the substituents on the lactone ring, postulated as all-cis. The compound (Fig. 1) is a hydrated stereoisomer of the N-acetylated lactone of polyoxamic acid, the crystal structure of which has already been reported (Saskena et al., 1986).

A search of the Cambridge Structural Database (Allen, 2002) finds 30 crystallographically characterized γ-lactones with a nitrogen substituent on the C atom adjacent to the carbonyl group, two of which are closely related to (I). One of these is the isomeric N-acetylated lactone of polyoxamic acid mentioned above, and the other has an azido substituent instead of the acetylamino group (Baird et al., 1987). Both of these have a mixture of cis and trans substituents on the ring, with the nitrogen substituent trans to the hydroxymethyl group, and the hydroxy group cis to one of these and trans to the other.

The lactone ring in (I) has an envelope conformation, with atom C2 as the flap angle; C2 lies 0.558 (4) Å out of the mean plane of the other four atoms (r.m.s. deviation 0.021 Å), and this mean plane makes a dihedral angle of 35.0 (2)° with the plane formed by atoms C1, C2 and C3. The acetylamino and hydroxymethyl substituents are equatorial, which the hydroxy substituent on C2 is axial.

Details of the hydrogen bonds are given in Table 2. The N—H and both O—H groups serve as donors, together with both O—H groups of the water molecule, and the acceptors are the two carbonyl O atoms (O5 accepts two hydrogen bonds), the OH atom O4 and the water O atom. All hydrogen bonds are intermolecular. Four hydrogen bonds per lactone molecule (O2 and N1 as donors, and O3 and O5 as acceptors link these into sheets, as shown in Fig. 2. Interactions with the water molecules crosslink the sheets into the full three-dimensional network, as shown in Fig. 3.

Experimental top

The compound was prepared as described by Jackson et al. (1995), and was recrystallized from ethanol, which is presumably the source of the water of crystallization.

Refinement top

Carbon-bound H atoms were placed geometrically and refined with a riding model (including free rotation about C—C bonds), and with Uiso constrained to be 1.2 (1.5 for methyl groups) times Ueq of the carrier atom. H atoms bonded to N and O were located in a difference map and were refined freely with individual isotropic displacement parameters. In the absence of significant anomalous scattering effects, Friedel pairs were merged. The absolute configuration was assumed from the known configuration of the starting material, viz. 2,3-isopropylidene-L-threitol.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: local programs; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Figures top
[Figure 1] Fig. 1. The structure of the asymmetric unit of (I), with atom labels and 50% probability ellipsoids for non-H atoms.
[Figure 2] Fig. 2. Sheets of lactone molecules formed by intermolecular hydrogen bonds, viewed along the c axis.
[Figure 3] Fig. 3. The crystal packing, viewed along the a axis, showing the linking of molecular sheets through hydrogen bonds with water molecules.
(I) top
Crystal data top
C7H11NO5·H2ODx = 1.437 Mg m3
Mr = 207.18Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 3459 reflections
a = 4.5292 (5) Åθ = 1.9–28.2°
b = 9.7807 (10) ŵ = 0.13 mm1
c = 21.622 (2) ÅT = 160 K
V = 957.83 (18) Å3Needle, colourless
Z = 40.30 × 0.08 × 0.04 mm
F(000) = 440
Data collection top
Bruker SMART 1K CCD
diffractometer
1101 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.047
Graphite monochromatorθmax = 28.4°, θmin = 1.9°
Detector resolution: 8.192 pixels mm-1h = 55
ω rotation with narrow frames scansk = 912
5877 measured reflectionsl = 2627
1352 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)] = 0.038H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.082 w = 1/[σ2(Fo2) + (0.0426P)2 + 0.0129P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
1352 reflectionsΔρmax = 0.25 e Å3
149 parametersΔρmin = 0.19 e Å3
0 restraintsExtinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.016 (3)
Crystal data top
C7H11NO5·H2OV = 957.83 (18) Å3
Mr = 207.18Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 4.5292 (5) ŵ = 0.13 mm1
b = 9.7807 (10) ÅT = 160 K
c = 21.622 (2) Å0.30 × 0.08 × 0.04 mm
Data collection top
Bruker SMART 1K CCD
diffractometer
1101 reflections with I > 2σ(I)
5877 measured reflectionsRint = 0.047
1352 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.082H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.25 e Å3
1352 reflectionsΔρmin = 0.19 e Å3
149 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.6310 (4)0.53995 (15)0.35100 (7)0.0191 (4)
C10.4114 (5)0.6463 (2)0.36592 (10)0.0170 (5)
H1A0.20890.60570.36450.020*
C20.4439 (6)0.7518 (2)0.31384 (10)0.0178 (5)
H2A0.25640.80300.30610.021*
O20.6866 (4)0.84040 (17)0.32424 (8)0.0229 (4)
H20.624 (7)0.916 (3)0.3363 (13)0.039 (9)*
C30.5289 (5)0.6597 (2)0.25947 (10)0.0159 (5)
H30.34650.61700.24200.019*
C40.7129 (5)0.5501 (2)0.29129 (11)0.0170 (5)
O30.9063 (4)0.48047 (16)0.26967 (8)0.0226 (4)
C50.4712 (6)0.6994 (2)0.42973 (11)0.0226 (6)
H5A0.67920.73000.43240.027*
H5B0.34320.77950.43780.027*
O40.4180 (5)0.5978 (2)0.47545 (8)0.0281 (4)
H40.581 (8)0.555 (3)0.4848 (15)0.049 (10)*
N10.6873 (5)0.7287 (2)0.21064 (9)0.0177 (4)
H10.797 (7)0.798 (3)0.2196 (13)0.033 (8)*
C60.6841 (6)0.6851 (2)0.15181 (11)0.0197 (5)
O50.5416 (4)0.58314 (17)0.13534 (7)0.0257 (4)
C70.8578 (6)0.7681 (3)0.10595 (11)0.0277 (6)
H7A0.72310.80780.07530.042*
H7B1.00110.70910.08500.042*
H7C0.96240.84160.12760.042*
O60.9079 (5)0.4663 (2)0.50663 (9)0.0282 (5)
H6A1.059 (11)0.503 (4)0.4918 (18)0.076 (14)*
H6B0.934 (8)0.454 (3)0.5467 (16)0.048 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0218 (9)0.0187 (8)0.0168 (8)0.0045 (7)0.0028 (7)0.0031 (7)
C10.0154 (11)0.0184 (11)0.0171 (11)0.0020 (10)0.0016 (10)0.0004 (9)
C20.0190 (12)0.0179 (11)0.0164 (11)0.0014 (10)0.0029 (10)0.0018 (9)
O20.0257 (9)0.0161 (9)0.0269 (9)0.0033 (8)0.0068 (8)0.0044 (8)
C30.0148 (11)0.0201 (11)0.0129 (11)0.0012 (9)0.0003 (9)0.0001 (9)
C40.0172 (11)0.0143 (10)0.0195 (12)0.0030 (10)0.0006 (10)0.0023 (9)
O30.0229 (9)0.0206 (8)0.0244 (9)0.0032 (7)0.0018 (8)0.0025 (7)
C50.0259 (14)0.0240 (12)0.0179 (12)0.0032 (11)0.0025 (11)0.0014 (10)
O40.0255 (10)0.0402 (11)0.0187 (9)0.0015 (9)0.0044 (8)0.0077 (8)
N10.0210 (11)0.0161 (10)0.0159 (10)0.0034 (9)0.0008 (8)0.0009 (8)
C60.0229 (12)0.0183 (11)0.0178 (12)0.0029 (11)0.0017 (11)0.0007 (9)
O50.0354 (11)0.0217 (8)0.0199 (9)0.0103 (8)0.0005 (8)0.0012 (7)
C70.0395 (17)0.0253 (13)0.0184 (12)0.0087 (12)0.0059 (12)0.0012 (11)
O60.0313 (11)0.0317 (11)0.0216 (10)0.0022 (9)0.0005 (9)0.0043 (8)
Geometric parameters (Å, º) top
O1—C11.475 (3)C5—H5A0.990
O1—C41.347 (3)C5—H5B0.990
C1—H1A1.000C5—O41.422 (3)
C1—C21.534 (3)O4—H40.87 (4)
C1—C51.499 (3)N1—H10.87 (3)
C2—H2A1.000N1—C61.341 (3)
C2—O21.418 (3)C6—O51.240 (3)
C2—C31.530 (3)C6—C71.504 (3)
O2—H20.83 (3)C7—H7A0.980
C3—H31.000C7—H7B0.980
C3—C41.523 (3)C7—H7C0.980
C3—N11.444 (3)O6—H6A0.84 (5)
C4—O31.204 (3)O6—H6B0.88 (3)
C1—O1—C4110.09 (16)C3—C4—O3128.4 (2)
O1—C1—H1A109.4C1—C5—H5A109.3
O1—C1—C2104.42 (17)C1—C5—H5B109.3
O1—C1—C5108.92 (19)C1—C5—O4111.52 (19)
H1A—C1—C2109.4H5A—C5—H5B108.0
H1A—C1—C5109.4H5A—C5—O4109.3
C2—C1—C5115.15 (19)H5B—C5—O4109.3
C1—C2—H2A112.3C5—O4—H4111 (2)
C1—C2—O2111.66 (19)C3—N1—H1119.3 (19)
C1—C2—C3101.10 (16)C3—N1—C6122.7 (2)
H2A—C2—O2112.3H1—N1—C6118.0 (19)
H2A—C2—C3112.3N1—C6—O5122.2 (2)
O2—C2—C3106.65 (19)N1—C6—C7116.6 (2)
C2—O2—H2109 (2)O5—C6—C7121.1 (2)
C2—C3—H3109.2C6—C7—H7A109.5
C2—C3—C4101.81 (17)C6—C7—H7B109.5
C2—C3—N1114.35 (18)C6—C7—H7C109.5
H3—C3—C4109.2H7A—C7—H7B109.5
H3—C3—N1109.2H7A—C7—H7C109.5
C4—C3—N1112.79 (19)H7B—C7—H7C109.5
O1—C4—C3109.53 (18)H6A—O6—H6B109 (4)
O1—C4—O3122.1 (2)
C4—O1—C1—C218.0 (2)C1—O1—C4—O3174.4 (2)
C4—O1—C1—C5141.52 (19)C2—C3—C4—O125.7 (2)
O1—C1—C2—O280.5 (2)C2—C3—C4—O3153.6 (2)
O1—C1—C2—C332.6 (2)N1—C3—C4—O1148.75 (19)
C5—C1—C2—O238.9 (3)N1—C3—C4—O330.6 (3)
C5—C1—C2—C3152.0 (2)O1—C1—C5—O466.9 (3)
C1—C2—C3—C434.4 (2)C2—C1—C5—O4176.3 (2)
C1—C2—C3—N1156.37 (19)C2—C3—N1—C6154.2 (2)
O2—C2—C3—C482.4 (2)C4—C3—N1—C690.1 (3)
O2—C2—C3—N139.5 (2)C3—N1—C6—O50.8 (4)
C1—O1—C4—C35.0 (2)C3—N1—C6—C7179.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O5i0.83 (3)1.90 (3)2.733 (2)176 (3)
O4—H4···O60.87 (4)1.78 (4)2.652 (3)178 (3)
N1—H1···O3ii0.87 (3)2.24 (3)3.104 (3)173 (3)
O6—H6A···O4iii0.84 (5)1.90 (5)2.729 (3)168 (4)
O6—H6B···O5iv0.88 (3)1.95 (3)2.834 (3)175 (3)
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x+2, y+1/2, z+1/2; (iii) x+1, y, z; (iv) x+3/2, y+1, z+1/2.

Experimental details

Crystal data
Chemical formulaC7H11NO5·H2O
Mr207.18
Crystal system, space groupOrthorhombic, P212121
Temperature (K)160
a, b, c (Å)4.5292 (5), 9.7807 (10), 21.622 (2)
V3)957.83 (18)
Z4
Radiation typeMo Kα
µ (mm1)0.13
Crystal size (mm)0.30 × 0.08 × 0.04
Data collection
DiffractometerBruker SMART 1K CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
5877, 1352, 1101
Rint0.047
(sin θ/λ)max1)0.668
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.082, 1.04
No. of reflections1352
No. of parameters149
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.25, 0.19

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2001), SHELXTL and local programs.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O5i0.83 (3)1.90 (3)2.733 (2)176 (3)
O4—H4···O60.87 (4)1.78 (4)2.652 (3)178 (3)
N1—H1···O3ii0.87 (3)2.24 (3)3.104 (3)173 (3)
O6—H6A···O4iii0.84 (5)1.90 (5)2.729 (3)168 (4)
O6—H6B···O5iv0.88 (3)1.95 (3)2.834 (3)175 (3)
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x+2, y+1/2, z+1/2; (iii) x+1, y, z; (iv) x+3/2, y+1, z+1/2.
 

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