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The mol­ecule of 2-(hydroxy­methyl)-1,3-propane­diol, C4H10O3, lies across a mirror plane in space group P21/m, with disorder of both terminal hydroxyl H atoms. The molecules are linked by three O-H...O hydrogen bonds which combine to form sheets; in each O-H...O bond, the H atom resonates between the two O atoms. In the crystal structure of N,N'-­bis­[2-hydroxy-1,1-bis­(hydroxy­methyl)­ethyl]­malon­amide, C11H22N2O8, the molecule lies about a twofold axis and has four strong hydrogen bonds which form a mixture of chains and dimers; these combine to give a three-dimensional supramolecular framework.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270102011800/sk1567sup1.cif
Contains datablocks global, VI, VII

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270102011800/sk1567VIsup2.hkl
Contains datablock VI

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270102011800/sk1567VIIsup3.hkl
Contains datablock VII

CCDC references: 193438; 193439

Comment top

The supramolecular structure of N,N'-bis[2-hydroxy-1,1-bis(hydroxymethyl)ethyl]ethanediamide, (HOCH2)3CNHCOCONHC(CH2OH)3, (I), was recently reported to be two-dimensional, despite the presence of six independent hydrogen bonds (Ross et al., 2001). The aminotriol parent of (I), namely H2NC(CH2OH)3, (II) (Eilerman & Rudman, 1980; Castellari & Ottani, 1997), also has a two-dimensional supramolecular structure in the orthorhombic phase, as does pentaerythritol, C(CH2OH)4, (III) (Ladd, 1979; Eilerman & Rudman, 1979a; Hope & Nichols, 1981; Semmingsen, 1988; Katrusiak, 1995; Batten & Robson, 1998). In contrast, the hydrogen-bonding arrangements in 3-hydroxy-2,2-bis(hydroxymethyl)propanoic acid, HO2CC(CH2OH)3, (IV) (Eilerman & Rudman, 1979b), and 2-ethyl-2-(hydroxymethyl)-1,3-propanediol, CH3CH2C(CH2OH)3, (V) (Zakaria et al., 2001), produce a three-dimensional array. The supramolecular structures of 2-(hydroxymethyl)-1,3-propanediol, (VI), and N,N'-bis-[2-hydroxy-1,1-bis(hydroxymethyl)ethyl]malonamide, (VII), have now been determined and compared to those of the structure of compounds (I)–(V).

A general view of the molecule of (VI) is shown in Fig. 1. Atoms C1, C2 and O1 lie on the mirror plane, leading to disorder of the hydroxyl H atom bonded to O1. Similarly, there is disorder of the second hydroxyl group, resulting in three strong hydrogen bonds (Table 1). In fact, it can be considered that the H atoms resonate between the O atoms, so that a continous network of hydrogen bonds forms. In Fig. 2, H atoms have been omitted to make this network clearer; the dashed lines represent O—H···O bonds where the H atom may be coordinated to either O atom. Two chains form: the first forms from O2—H2C···O1iv [symmetry code: (iv) 1 - x, y - 1/2, 1 - z] leading to a C(8) chain along (010), which combine to form a series of R22(12) rings (Fig. 2). The second chain forms from a combination of the first hydrogen bond and O2—H2B···O2iii [symmetry code: (iii) -x, -y, -z] to give C(8) chains and R44(12) rings; these combine to form a sheet (Fig. 2), shown normal to [100].

A sheet arrangement of molecules was also found for the trihydroxy compound, (V) (Zakaria et al., 2001). The framework in (V) consists of parallel molecular ladders, generated by two of the three O—H···O hydrogen bonds. The ladders are linked together by the third hydrogen bond (Zakaria et al., 2001). In the tetrahydroxy compound, (III), the two-dimensional (sheet) structure is created by each molecule linking to four others by O—H···O hydrogen bonds; all the hydroxyl groups in (III) act as hydrogen-bond acceptors and donors (Ladd, 1979; Eilerman & Rudman, 1979a; Hope & Nichols, 1981; Semmingsen, 1988; Katrusiak, 1995; Batten & Robson, 1998).

N,N'-Bis-2-hydroxy-1,1-bis(hydroxymethyl)ethyl]malonamide, (VII) (Fig. 3), crystallizes in spacegroup C2/c with atom C6 on the 4 e s pecial positions; the remainder of the atoms are located in general positions with the full molecule generated by the c-glide (symmetry code: -x, y, 1/2 - z).

Four strong hydrogen bonds form (Table 2); amide atom N1 donates to hydroxyl atom O3 [N1—H1···O3(x, y + 1, z)], to form a C(5) chain along [010]. The symmetry of the molecule leads to two parallel C(5) chains giving linked R22(18) rings (Fig. 4). The hydroxyl atoms O2 and O4 act as both donor and acceptor; O4—H4···O2(-1/2 + x, 1/2 + y, z) leads to a C(13) chain along [110] whilst O2—H2···O4(1/2 - x, 1/2 - y, 1 - z) gives rise to a dimer centred on the inversion at (1/4, 1/4, 1/2) leading to an R22(12) motif. The two combine to give a sheet containing adjacent R44(8) and R22(12) rings (Fig. 5) O2—H2···O4—H4···O2. The final hydrogen bond again has a hydroxyl O atom as donor, but with the CO as acceptor; O3—H3···O1(1/2 + x, -1/2 + y, z), thus generating a C(7) chain along [110]. The four hydrogen bonds combine in a number of ways. In addition to the formation of the R44(8) ring shown in Fig. 5, C(5) and C(7) combine to form an R22(8) ring, whilst C(7) and C(13) combine to give an R22(13) motif; both of these are shown in Fig. 6. Finally, all hydrogen bonds combine via the linking dimer to form a three-dimensional framework (Fig. 7).

The additional methylene group in (VII) results in significant structural differences between (I) (Ross et al., 2001) and (VII), the most striking being the change from a two-dimensional supramolecular network in (I) to the three-dimensional arrangement in (VII). The amido NH units in (I) take no part in the supramolecular aggregation, being solely involved in intramolecular hydrogen bonding with the adjacent carbonyl O atoms (Ross et al., 2001). Each molecule of (I) acts as a fourfold donor and acceptor in intermolecular hydrogen bonding and each molecule of (I) is thereby linked to six others in the resulting two-dimensional array (Ross et al., 2001). In the aminotriol, (II), the amino group is involved in the intermolecular hydrogen bonding. However, despite there being four distinct hydrogen bonds [two O—H···O, one O—H···N and one N—H···O], the supramolecular structure is only two-dimensional (Eilerman & Rudman, 1980; Castellari & Ottani, 1997).

Experimental top

Compound (VI) was a commercial sample and was recrystallized from dry ethyl acetate. Compound (VII) was prepared from (II) (0.045 mol) and diethyl malonate (0.023 mol) in refluxing methanol for 2 h. On cooling, colourless crystals of (VII) slowly formed. The product was recrystallized from aqueous EtOH (yield 90%, m.p. 428 K). 1H NMR (Me2SO-d6, p.p.m.): δ 3.15 (s, 2H, COCH2), 3.539 (d, 12H, CH2OH), 4.63 (t, 6H, OH), 7.55 (s, 2H, NH). 13C NMR (Me2SO-d6, p.p.m.): δ 44.4 (COCH2), 60.6 (CH2OH), 62.9 (C-quarternary), 168.8 (CO). IR (KBr): ν 3361 and 3308 (OH), 3217 (NH), 2970, 2953 and 2883 (CH), 1648 (CO).

Refinement top

All H atoms were placed in geometrical positions and refined using a riding model. PLATON (Spek, 2002) was used for analysis of hydrogen bonding.

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998) for (VI); SMART (Bruker, 1998) for (VII). Cell refinement: DENZO and COLLECT for (VI); SAINT (Bruker, 2000) for (VII). Data reduction: DENZO and COLLECT for (VI); SAINT for (VII). For both compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX in OSCAIL (McArdle, 1994, 2000) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. A view of the molecule of (VI), showing the atom-numbering scheme. The molecule lies across the mirror [symmetry code: (i) x, -y + 1/2, z]. Dashed lines indicate disorder of the terminal H atoms. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres.
[Figure 2] Fig. 2. Arrangement of molecules of (VI) within the unit cell, showing formation of sheets normal to [100]. Dashed lines indicate O—H···O bonds in which H atoms resonate between the two O atoms, as indicated by the disorder as shown in Fig. 1.
[Figure 3] Fig. 3. A view of the molecule of (VII), showing the atom-numbering scheme, and the formation of the molecule via symmetry operation [symmetry code: (i) -x, y, -z + 1/2]. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres.
[Figure 4] Fig. 4. Part of the crystal structure of (VII), showing the C(5) chains formed from N1—H1···O3ii hydrogen bonds [symmetry code: (ii) x, y + 1, z].
[Figure 5] Fig. 5. Part of the crystal structure of (VII), showing the sheets formed from two hydrogen bonds [O2—H2···O4iv and O4—H4···O2iii; symmetry codes: (iii) -1/2 + x, 1/2 + y, z; (iv) 1/2 - x, 1/2 - y, 1 - z] resulting in an R44(8) ring, viz. O4—H4···O2ii—H2ii···O4vi—H4vi····O2iii—H2iii···O4 [symmetry codes: (ii) x, y + 1, z; (vi) -1/2 - x, 1/2 + y, 1/2 - z].
[Figure 6] Fig. 6. Combination of three hydrogen bonds in the structure of (VII), i.e. N1—H1···O3, O3—H3···O1 and O4—H4···O2. This gives C(5), C(7) and C(13) chains which combine to give R22(8) and R22(13) rings. [Symmetry codes: (iii) -1/2 + x, 1/2 + y, z; (vi) -1/2 - x, 1/2 + y, 1/2 - z].
[Figure 7] Fig. 7. The unit cell of (VII), showing the formation of a three-dimensional framework of hydrogen bonds.
(VI) 2-(hydroxymethyl)-1,2-propanediol top
Crystal data top
C4H10O3F(000) = 116
Mr = 106.12Dx = 1.320 Mg m3
Monoclinic, P21/mMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybCell parameters from 1123 reflections
a = 4.8066 (3) Åθ = 2.9–27.5°
b = 9.5179 (6) ŵ = 0.11 mm1
c = 6.1346 (4) ÅT = 292 K
β = 107.911 (4)°Prism, colourless
V = 267.05 (3) Å30.26 × 0.12 × 0.05 mm
Z = 2
Data collection top
Enraf-Nonius KappaCCD
diffractometer
629 independent reflections
Radiation source: fine-focus sealed tube504 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
ϕω scansθmax = 27.4°, θmin = 3.5°
Absorption correction: empirical (using intensity measurements)
(SORTAV; Blessing, 1995, 1997)
h = 56
Tmin = 0.949, Tmax = 0.994k = 1211
2166 measured reflectionsl = 77
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)] = 0.036H-atom parameters constrained
wR(F2) = 0.103 w = 1/[σ2(Fo2) + (0.0523P)2 + 0.0278P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
629 reflectionsΔρmax = 0.17 e Å3
46 parametersΔρmin = 0.16 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.21 (5)
Crystal data top
C4H10O3V = 267.05 (3) Å3
Mr = 106.12Z = 2
Monoclinic, P21/mMo Kα radiation
a = 4.8066 (3) ŵ = 0.11 mm1
b = 9.5179 (6) ÅT = 292 K
c = 6.1346 (4) Å0.26 × 0.12 × 0.05 mm
β = 107.911 (4)°
Data collection top
Enraf-Nonius KappaCCD
diffractometer
629 independent reflections
Absorption correction: empirical (using intensity measurements)
(SORTAV; Blessing, 1995, 1997)
504 reflections with I > 2σ(I)
Tmin = 0.949, Tmax = 0.994Rint = 0.038
2166 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.103H-atom parameters constrained
S = 1.04Δρmax = 0.17 e Å3
629 reflectionsΔρmin = 0.16 e Å3
46 parameters
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*/UeqOcc. (<1)
C20.2426 (3)0.25000.2648 (3)0.0329 (4)
H2A0.04090.25000.16220.039*
C10.2268 (4)0.25000.5080 (3)0.0393 (5)
H1A0.12000.33240.53040.047*
O10.5093 (3)0.25000.6743 (2)0.0468 (4)
H10.56820.16890.69980.062 (9)*0.50
C30.3879 (3)0.11876 (11)0.21179 (19)0.0381 (4)
H3A0.41990.12880.06400.046*
H3B0.57660.10620.32680.046*
O20.2094 (2)0.00105 (9)0.20882 (17)0.0518 (4)
H2B0.094 (8)0.001 (4)0.079 (7)0.078*0.50
H2C0.293 (8)0.073 (5)0.236 (6)0.078*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C20.0341 (8)0.0254 (8)0.0340 (8)0.0000.0029 (6)0.000
C10.0408 (9)0.0344 (9)0.0435 (10)0.0000.0144 (7)0.000
O10.0587 (8)0.0382 (8)0.0348 (7)0.0000.0016 (5)0.000
C30.0466 (7)0.0277 (6)0.0380 (7)0.0000 (5)0.0102 (5)0.0030 (4)
O20.0667 (7)0.0254 (5)0.0535 (7)0.0061 (4)0.0040 (5)0.0018 (4)
Geometric parameters (Å, º) top
C2—C31.5146 (13)C3—O21.4239 (14)
C2—C11.517 (2)C3—H3A0.9700
C2—H2A0.9800C3—H3B0.9700
C1—O11.426 (2)O2—H2B0.82 (4)
C1—H1A0.9700O2—H2C0.79 (4)
O1—H10.8200
C3—C2—C3i111.13 (12)O2—C3—H3A109.6
C3—C2—C1112.15 (8)C2—C3—H3A109.6
C3—C2—H2A107.0O2—C3—H3B109.6
C1—C2—H2A107.0C2—C3—H3B109.6
O1—C1—C2112.28 (13)H3A—C3—H3B108.1
O1—C1—H1A109.1C3—O2—H2B104 (3)
C2—C1—H1A109.1C3—O2—H2C115 (3)
C1—O1—H1109.5H2B—O2—H2C110 (4)
O2—C3—C2110.32 (10)
C3—C2—C1—O162.93 (9)C1—C2—C3—O267.63 (13)
C3i—C2—C3—O2165.95 (8)
Symmetry code: (i) x, y+1/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2ii0.821.912.7130 (11)167
O2—H2B···O2iii0.82 (4)1.91 (4)2.729 (2)173 (4)
O2—H2C···O1iv0.79 (4)1.93 (4)2.7130 (11)175 (4)
Symmetry codes: (ii) x+1, y, z+1; (iii) x, y, z; (iv) x+1, y1/2, z+1.
(VII) N,N'-bis[2-hydroxy-1,1-bis(hydroxymethyl)ethyl]malonamide top
Crystal data top
C11H22N2O8F(000) = 664
Mr = 310.31Dx = 1.484 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3982 reflections
a = 11.6928 (11) Åθ = 3.7–32.3°
b = 5.6610 (5) ŵ = 0.13 mm1
c = 21.0034 (19) ÅT = 292 K
β = 92.700 (2)°Plate, colourless
V = 1388.7 (2) Å30.50 × 0.50 × 0.10 mm
Z = 4
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
2473 independent reflections
Radiation source: fine-focus sealed tube2027 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
ϕω scansθmax = 32.5°, θmin = 3.5°
Absorption correction: multi-scan
(SADABS; Bruker, 1999)
h = 1017
Tmin = 0.817, Tmax = 0.928k = 88
6754 measured reflectionsl = 3131
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.187H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.1186P)2 + 0.6984P]
where P = (Fo2 + 2Fc2)/3
2473 reflections(Δ/σ)max < 0.001
103 parametersΔρmax = 0.46 e Å3
0 restraintsΔρmin = 0.27 e Å3
Crystal data top
C11H22N2O8V = 1388.7 (2) Å3
Mr = 310.31Z = 4
Monoclinic, C2/cMo Kα radiation
a = 11.6928 (11) ŵ = 0.13 mm1
b = 5.6610 (5) ÅT = 292 K
c = 21.0034 (19) Å0.50 × 0.50 × 0.10 mm
β = 92.700 (2)°
Data collection top
Bruker SMART 1000 CCD area-detector
diffractometer
2473 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1999)
2027 reflections with I > 2σ(I)
Tmin = 0.817, Tmax = 0.928Rint = 0.040
6754 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.187H-atom parameters constrained
S = 1.06Δρmax = 0.46 e Å3
2473 reflectionsΔρmin = 0.27 e Å3
103 parameters
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.

Reflections 6 0 14 and 6 0 16 were omitted from the refinement as these gave an anomalously poor fit.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.18283 (10)0.0069 (2)0.37960 (5)0.0214 (2)
C20.30828 (11)0.0892 (2)0.39066 (6)0.0273 (3)
H2A0.34710.07720.35100.033*
H2B0.30920.25370.40350.033*
O20.36882 (10)0.0482 (2)0.43840 (6)0.0388 (3)
H20.37460.02720.47170.058*
C30.17427 (12)0.2557 (2)0.36034 (7)0.0284 (3)
H3A0.20770.35110.39480.034*
H3B0.09410.29840.35480.034*
O30.22973 (10)0.3107 (2)0.30335 (5)0.0345 (3)
H30.29500.35680.31230.052*
C40.11605 (13)0.0373 (2)0.44108 (6)0.0293 (3)
H4A0.04420.04780.43630.035*
H4B0.16010.03200.47660.035*
O40.09299 (10)0.2793 (2)0.45517 (5)0.0353 (3)
H40.02980.31570.43960.053*
N10.13697 (9)0.15798 (19)0.32724 (5)0.0230 (2)
H10.18500.24350.30780.028*
C50.02636 (11)0.1730 (2)0.30746 (6)0.0234 (2)
O10.05086 (9)0.0641 (2)0.33328 (6)0.0406 (3)
C60.00000.3319 (3)0.25000.0246 (3)
H6A0.0696 (18)0.428 (4)0.2556 (10)0.034 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0242 (5)0.0226 (5)0.0172 (5)0.0016 (4)0.0019 (4)0.0007 (3)
C20.0242 (6)0.0303 (6)0.0267 (5)0.0010 (4)0.0059 (4)0.0027 (4)
O20.0393 (6)0.0394 (6)0.0361 (5)0.0150 (5)0.0149 (5)0.0085 (4)
C30.0305 (6)0.0237 (5)0.0311 (6)0.0004 (4)0.0032 (5)0.0017 (4)
O30.0322 (5)0.0374 (5)0.0340 (5)0.0045 (4)0.0018 (4)0.0111 (4)
C40.0347 (7)0.0326 (6)0.0210 (5)0.0055 (5)0.0046 (5)0.0034 (4)
O40.0385 (6)0.0400 (6)0.0271 (5)0.0120 (4)0.0025 (4)0.0089 (4)
N10.0221 (5)0.0256 (5)0.0211 (4)0.0014 (3)0.0000 (3)0.0040 (3)
C50.0234 (5)0.0263 (5)0.0206 (5)0.0008 (4)0.0003 (4)0.0002 (4)
O10.0242 (5)0.0584 (7)0.0392 (6)0.0039 (5)0.0014 (4)0.0191 (5)
C60.0294 (8)0.0255 (7)0.0184 (6)0.0000.0054 (6)0.000
Geometric parameters (Å, º) top
C1—N11.4740 (15)O3—H30.8200
C1—C31.5429 (17)C4—O41.4301 (17)
C1—C21.5460 (18)C4—H4A0.9700
C1—C41.5496 (17)C4—H4B0.9700
C2—O21.4299 (16)O4—H40.8200
C2—H2A0.9700N1—C51.3424 (16)
C2—H2B0.9700N1—H10.8600
O2—H20.8200C5—O11.2392 (16)
C3—O31.4224 (17)C5—C61.5251 (16)
C3—H3A0.9700C6—C5i1.5250 (16)
C3—H3B0.9700C6—H6A0.99 (2)
N1—C1—C3110.27 (10)H3A—C3—H3B107.7
N1—C1—C2104.28 (10)C3—O3—H3109.5
C3—C1—C2112.26 (10)O4—C4—C1112.71 (11)
N1—C1—C4112.18 (10)O4—C4—H4A109.1
C3—C1—C4107.24 (10)C1—C4—H4A109.1
C2—C1—C4110.69 (10)O4—C4—H4B109.1
O2—C2—C1112.11 (11)C1—C4—H4B109.1
O2—C2—H2A109.2H4A—C4—H4B107.8
C1—C2—H2A109.2C4—O4—H4109.5
O2—C2—H2B109.2C5—N1—C1125.38 (10)
C1—C2—H2B109.2C5—N1—H1117.3
H2A—C2—H2B107.9C1—N1—H1117.3
C2—O2—H2109.5O1—C5—N1122.98 (12)
O3—C3—C1113.90 (11)O1—C5—C6121.04 (11)
O3—C3—H3A108.8N1—C5—C6115.98 (10)
C1—C3—H3A108.8C5i—C6—C5107.69 (14)
O3—C3—H3B108.8C5i—C6—H6A106.3 (12)
C1—C3—H3B108.8C5—C6—H6A111.4 (12)
N1—C1—C2—O2177.01 (10)C2—C1—C4—O471.84 (14)
C3—C1—C2—O257.64 (14)C3—C1—N1—C569.30 (15)
C4—C1—C2—O262.15 (13)C2—C1—N1—C5169.99 (12)
N1—C1—C3—O356.21 (14)C4—C1—N1—C550.16 (16)
C2—C1—C3—O359.59 (14)C1—N1—C5—O12.5 (2)
C4—C1—C3—O3178.62 (11)C1—N1—C5—C6176.91 (10)
N1—C1—C4—O444.19 (15)O1—C5—C6—C5i73.77 (13)
C3—C1—C4—O4165.40 (11)N1—C5—C6—C5i105.60 (11)
Symmetry code: (i) x, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3ii0.862.583.2445 (16)135
O4—H4···O2iii0.822.032.8037 (16)157
O2—H2···O4iv0.821.912.7238 (15)172
O3—H3···O1v0.821.892.7069 (16)175
C4—H4A···O10.972.472.9227 (19)108
Symmetry codes: (ii) x, y+1, z; (iii) x1/2, y+1/2, z; (iv) x+1/2, y+1/2, z+1; (v) x+1/2, y1/2, z.

Experimental details

(VI)(VII)
Crystal data
Chemical formulaC4H10O3C11H22N2O8
Mr106.12310.31
Crystal system, space groupMonoclinic, P21/mMonoclinic, C2/c
Temperature (K)292292
a, b, c (Å)4.8066 (3), 9.5179 (6), 6.1346 (4)11.6928 (11), 5.6610 (5), 21.0034 (19)
β (°) 107.911 (4) 92.700 (2)
V3)267.05 (3)1388.7 (2)
Z24
Radiation typeMo KαMo Kα
µ (mm1)0.110.13
Crystal size (mm)0.26 × 0.12 × 0.050.50 × 0.50 × 0.10
Data collection
DiffractometerEnraf-Nonius KappaCCD
diffractometer
Bruker SMART 1000 CCD area-detector
diffractometer
Absorption correctionEmpirical (using intensity measurements)
(SORTAV; Blessing, 1995, 1997)
Multi-scan
(SADABS; Bruker, 1999)
Tmin, Tmax0.949, 0.9940.817, 0.928
No. of measured, independent and
observed [I > 2σ(I)] reflections
2166, 629, 504 6754, 2473, 2027
Rint0.0380.040
(sin θ/λ)max1)0.6480.755
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.103, 1.04 0.048, 0.187, 1.06
No. of reflections6292473
No. of parameters46103
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.17, 0.160.46, 0.27

Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), SMART (Bruker, 1998), DENZO and COLLECT, SAINT (Bruker, 2000), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEX in OSCAIL (McArdle, 1994, 2000) and ORTEP-3 for Windows (Farrugia, 1997), SHELXL97.

Hydrogen-bond geometry (Å, º) for (VI) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.821.912.7130 (11)167
O2—H2B···O2ii0.82 (4)1.91 (4)2.729 (2)173 (4)
O2—H2C···O1iii0.79 (4)1.93 (4)2.7130 (11)175 (4)
Symmetry codes: (i) x+1, y, z+1; (ii) x, y, z; (iii) x+1, y1/2, z+1.
Hydrogen-bond geometry (Å, º) for (VII) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3i0.862.583.2445 (16)135
O4—H4···O2ii0.822.032.8037 (16)157
O2—H2···O4iii0.821.912.7238 (15)172
O3—H3···O1iv0.821.892.7069 (16)175
C4—H4A···O10.972.472.9227 (19)108
Symmetry codes: (i) x, y+1, z; (ii) x1/2, y+1/2, z; (iii) x+1/2, y+1/2, z+1; (iv) x+1/2, y1/2, z.
 

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