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Molecules of the title compound, C10H20N2O8, adopt a conformation which is almost centrosymmetric. The mol­ecules are disordered over two sets of sites with an occupancy ratio of 0.94:0.06. In the major form, there are two intramolecular O—H...O hydrogen bonds [O...O 2.756 (4) and 2.765 (4) Å; O—H...O 144 and 146°], in which the two amidic O atoms act as acceptors. In addition, there are four intermolecular O—H...O hydrogen bonds [O...O 2.650 (3)–2.666 (3) Å; O—H...O 158–171°]; these link each mol­ecule to six others in a continuous sheet structure which contains five distinct ring motifs, two of the S(7) type, two of the R^3_3(10) type and one of the R^2_2(22) type.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101008940/gg1060sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101008940/gg1060Isup2.hkl
Contains datablock I

CCDC reference: 170191

Comment top

Molecules of pentaerythritol, C(CH2OH)4, have crystallographically imposed 4 (S4) symmetry in the solid state and the hydroxyl groups act as both hydrogen-bond donors and hydrogen-bond acceptors; the molecules are linked by the O—H···O hydrogen bonds into sheets built from R44(8) and R22(12) rings arranged in a checkerboard fashion (Ladd, 1979; Eilerman & Rudman, 1979a; Hope & Nichols, 1981; Semmingsen, 1988; Katrusiak, 1995). Although each molecule participates in eight hydrogen bonds, and is thereby linked to four other molecules in a (4, 4) net (Batten & Robson, 1998), the elegant simplicity of the supramolecular structure owes much to the symmetry equivalence of all the hydrogen bonds.

In the ordered orthorhombic phase of the related aminotriol H2NC(CH2OH)3 (Eilerman & Rudman, 1980; Castellari & Ottani, 1997), the amino group and the three hydroxyl groups all act as both donors and acceptors of hydrogen bonds. However, since the molecules lie in general positions, there are four distinct hydrogen bonds in the structure, two of O—H···O type and one each of O—H···N and N—H···O types; the hydrogen bonding is thus of considerable complexity although the supramolecular aggregation is still two-dimensional, as in pentaerythritol. There is also a cubic plastic phase of this material, with Z = 2 in space group Im3m (Eilerman & Rudman, 1980), but the orientational disorder of the molecules in this phase precludes detailed discussion of the hydrogen bonding. By contrast, in tris-hydroxymethyl)acetic acid HOOCC(CH2OH)3 (Eilerman & Rudman, 1979b), the hydrogen bonding generates a three-dimensional supramolecular structure, although the R22(8) motif so characteristic of carboxylic acids is absent: this material also exhibits a disordered cubic phase, with Z = 4 in space group Fm3m (Eilerman & Rudman, 1973).

In view of the two-dimensional aggregation in both C(CH2OH)4 and ordered H2NC(CH2OH)3, and the three-dimensional aggregation in ordered HOOCC(CH2OH)3, it is therefore of interest to investigate the structure of the related hexahydroxy analogue N,N'-bis[tris(hydroxymethyl)methyl]ethanediamide, (HOCH2)3CNHCOCONHC(CH2OH)3, (I), originally synthesized (DuBois et al., 1992) as one of the more recent examples in a long series of adventitious sweetening agents (Exodus, undated; Grami, 1998). \sch

Molecules of (I) (Fig. 1) lie in general positions in space group Pna21; they are disordered over two sets of sites with occupancies 0.94 and 0.06, and the two sets of sites are approximately related to one another by reflection across the plane y = 0.75. Because of the constraints applied to the minor component, only the major component will be discussed. For the major form, the overall dimensions and the conformation indicate that the molecules are close to being centrosymmetric: in particular, corresponding pairs of torsional angles have closely-similar magnitudes with opposite signs. However, a search for possible additional symmetry showed that none was present; this is so even if all the H atoms are ignored. The non-centrosymmetric nature of the molecules in (I) may be contrasted with the behaviour of the derivatives (II)-(IV), in all of which the molecules lie across centres of inversion (Ross et al., 1996a,b). The central portion of the molecule is essentially planar, with neighbouring N—H and CO units mutually trans: the central C—C bond is long, as typically found in oxalic acid derivatives (de With & Harkema, 1977; Allen et al., 1987; Ross et al., 1996a,b).

Each of the hydroxyl groups in (I) acts both as a hydrogen-bond donor and as a hydrogen-bond acceptor, but the N—H units play no role in the supramolecular aggregation (Table 2). There are two intramolecular O—H···O hydrogen bonds, each of which generates an S(7) motif (Fig. 2). Each molecules therefore acts as a fourfold donor and acceptor in intermolecular hydrogen bonds, and each molecule is thereby linked to six others in the resulting two-dimensional structure, but by adoption of the sub-structure approach (Gregson et al., 2000), the rather complex supramolecular aggregation can readily be analysed in terms of three simple motifs.

Atoms O13 and O23 in the molecule at (x, y, z) act as donors to O14 at (x, -1 + y, z) and to O24 at (x, 1 + y, z), respectively. Propagation of these two hydrogen bonds generates a molecular ladder running parallel to the [010] direction: the two rungs of the ladder consist of independent C(6) chains, while the molecular backbone from O13 to O23 provides the rungs of the ladder (Fig. 2). Between the rungs there are R22(22) rings, in the interior of which are the S(7) rings.

The [010] ladders are linked by two independent spiral-chain motifs. Atom O14 in the molecule at (x, y, z) acts as donor to O23 at (-1/2 + x, 3/2 - y, z), while O14 at (-1/2 + x, 3/2 - y, z) in turn acts as donor to O23 at (-1 + x, y, z); in this manner is generated a C(11) spiral around the 21 screw axis along (x, 3/4, 0). Similarly, O24 at (x, y, z) acts as donor to O13 at (1/2 + x, 1/2 - y, z) and propagation of this interaction generates a second C(11) spiral around the 21 screw axis along (x, 1/2, 0). The combined effect of these two independent C(11) chains along [100] is to link the [010] ladders into a sheet parallel to (001). This sheet is built from two types of R33(10) ring in addition to the R22(22) ring and the two types of S(7) ring noted earlier (Fig. 2). The reference (001) sheet lies in the domain -0.09 < z < 0.47, and a second sheet runs through the unit cell in the domain 0.41 < z < 0.97. There are no hydrogen bonds between adjacent sheets, so that the supramolecular aggregation is two-dimensional.

Related literature top

For related literature, see: Allen et al. (1987); Batten & Robson (1998); Castellari & Ottani (1997); DuBois, Zhi, Roy, Stevens & Yalpani (1992); Eilerman & Rudman (1973, 1979a, 1979b, 1980); Flack (1983); Flack & Bernardinelli (2000); Grami (1998); Gregson et al. (2000); Hope & Nichols (1981); Katrusiak (1995); Ladd (1979); Ross et al. (1996a, 1996b); Semmingsen (1988); With & Harkema (1977).

Experimental top

A sample of (I) was prepared according to the published procedure (DuBois et al., 1992). Crystals suitable for single-crystal X-ray diffraction were obtained from a solution in ethanol.

Refinement top

Compound (I) is orthorhombic. The systematic absences permitted Pna21 and Pnam as possible space groups; since the unit-cell volume indicated Z = 4, Pna21 was selected, and confirmed by the subsequent structure analysis: no additional symmetry could be detected in the refined structure. H atoms were treated as riding with C—H 0.99 Å, N—H 0.88 Å, O—H 0.84 Å. The quality of the diffraction data was poor, even at 150 (2) K, with R(int) of 0.101. It was apparent from the residual electron densities that the diffraction data could not be completely satisfied by just one molecular orientation, and it became clear that there was a small contribution from a second orientation of the molecule, whose occupancy derived from various refinements ranged from 0.058 (3) to 0.066 (3), and whose coordinates were approximately related to those of the major form by reflection across the plane y = 0.75. Free refinement of this component led to highly unrealistic interatomic distances and so it was handled via an extensive series of DFIX commands constraining all of the distances and some of the angles. O21B lay at the centre of a rather broad region of residual electron density, and attempts to refine its coordinates were unsuccessful: accordingly, its coordinates were fixed. To ensure the stability of the final refinements, the minor component was assigned a common isotropic displacement parameter and the occupancy was fixed at 0.06. In the absence of any significant anomalous scatterers, the refined Flack parameter (Flack, 1983) of -1.3 (18) was inconclusive (Flack & Bernardinelli, 2000); hence the Friedel equivalents were merged before the final refinements.

Computing details top

Data collection: Kappa-CCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2001); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and PRPKAPPA (Ferguson, 1999).

Figures top
[Figure 1] Fig. 1. The major form of of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Part of the crystal structure of (I) showing formation of a (001) sheet. For the sake of clarity, only the major form is shown, and H atoms bonded to C or N are omitted. Atoms marked with a star (*), hash (#), dollar sign () or ampersand (&) are at the symmetry positions (x, -1 + y, z), (x, 1 + y, z), (-1/2 + x, 3/2 - y, z) and (1/2 + x, 1/2 - y, z), respectively.
N,N'-Bis[tris(hydroxymethyl)methyl]ethanediamide top
Crystal data top
C10H20N2O8Dx = 1.484 Mg m3
Mr = 296.28Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21Cell parameters from 9375 reflections
a = 21.4097 (3) Åθ = 2.9–27.5°
b = 6.1559 (6) ŵ = 0.13 mm1
c = 10.0605 (13) ÅT = 150 K
V = 1325.9 (2) Å3Needle, colourless
Z = 40.30 × 0.10 × 0.10 mm
F(000) = 632
Data collection top
Kappa-CCD
diffractometer
1573 independent reflections
Radiation source: fine-focus sealed X-ray tube1282 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.101
ϕ scans, and ω scans with κ offsetsθmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
h = 2527
Tmin = 0.962, Tmax = 0.987k = 67
7853 measured reflectionsl = 912
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.080P)2]
where P = (Fo2 + 2Fc2)/3
1573 reflections(Δ/σ)max = 0.001
235 parametersΔρmax = 0.26 e Å3
36 restraintsΔρmin = 0.28 e Å3
Crystal data top
C10H20N2O8V = 1325.9 (2) Å3
Mr = 296.28Z = 4
Orthorhombic, Pna21Mo Kα radiation
a = 21.4097 (3) ŵ = 0.13 mm1
b = 6.1559 (6) ÅT = 150 K
c = 10.0605 (13) Å0.30 × 0.10 × 0.10 mm
Data collection top
Kappa-CCD
diffractometer
1573 independent reflections
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
1282 reflections with I > 2σ(I)
Tmin = 0.962, Tmax = 0.987Rint = 0.101
7853 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04736 restraints
wR(F2) = 0.120H-atom parameters constrained
S = 1.02Δρmax = 0.26 e Å3
1573 reflectionsΔρmin = 0.28 e Å3
235 parameters
Special details top

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm [Fox, G·C. & Holmes, K·C. (1966). Acta Cryst. 20, 886–891] which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C110.35599 (14)0.3989 (5)0.2429 (4)0.0200 (7)0.94
O110.37908 (11)0.2156 (3)0.2587 (4)0.0296 (7)0.94
N110.29955 (12)0.4639 (4)0.2785 (3)0.0207 (6)0.94
C120.24894 (13)0.3321 (4)0.3355 (4)0.0180 (6)0.94
C130.22009 (14)0.1975 (5)0.2239 (4)0.0215 (8)0.94
O130.16741 (10)0.0787 (3)0.2706 (3)0.0265 (6)0.94
C140.20187 (15)0.4947 (5)0.3908 (4)0.0228 (7)0.94
O140.18617 (9)0.6547 (3)0.2946 (3)0.0255 (6)0.94
C150.27109 (15)0.1848 (5)0.4504 (4)0.0247 (8)0.94
O150.29531 (11)0.0194 (4)0.4106 (3)0.0287 (6)0.94
C210.39443 (13)0.5817 (4)0.1789 (4)0.0202 (7)0.94
O210.37160 (10)0.7631 (3)0.1637 (4)0.0262 (6)0.94
N210.45178 (12)0.5185 (4)0.1451 (3)0.0202 (6)0.94
C220.50150 (13)0.6557 (4)0.0900 (4)0.0195 (7)0.94
C230.53100 (15)0.7838 (5)0.2040 (4)0.0211 (8)0.94
O230.58211 (9)0.9099 (3)0.1575 (3)0.0257 (5)0.94
C240.54960 (15)0.4980 (5)0.0314 (4)0.0224 (7)0.94
O240.56664 (9)0.3349 (3)0.1241 (3)0.0252 (6)0.94
C250.47878 (15)0.8090 (5)0.0215 (4)0.0236 (7)0.94
O250.45581 (11)1.0118 (3)0.0231 (3)0.0268 (6)0.94
C11B0.3544 (10)1.0900 (4)0.247 (2)0.040*0.06
O11B0.3772 (12)1.2689 (9)0.2611 (15)0.040*0.06
N11B0.2994 (9)1.0298 (4)0.279 (2)0.040*0.06
C12B0.2505 (12)1.165 (4)0.338 (4)0.040*0.06
C13B0.221 (2)1.300 (8)0.227 (4)0.040*0.06
O13B0.1675 (16)1.413 (6)0.272 (7)0.040*0.06
C14B0.204 (3)0.997 (7)0.392 (5)0.040*0.06
O14B0.1869 (18)0.844 (6)0.294 (6)0.040*0.06
C15B0.273 (3)1.312 (6)0.451 (5)0.040*0.06
O15B0.294 (2)1.516 (5)0.405 (5)0.040*0.06
C21B0.3933 (19)0.910 (6)0.182 (6)0.040*0.06
O21B0.37100.72950.16020.040*0.06
N21B0.4517 (19)0.963 (7)0.153 (6)0.040*0.06
C22B0.5022 (15)0.841 (4)0.090 (5)0.040*0.06
C23B0.530 (2)0.709 (8)0.203 (5)0.040*0.06
O23B0.5832 (17)0.589 (6)0.161 (7)0.040*0.06
C24B0.549 (3)1.002 (7)0.032 (5)0.040*0.06
O24B0.5676 (17)1.165 (6)0.123 (6)0.040*0.06
C25B0.478 (3)0.698 (7)0.021 (5)0.040*0.06
O25B0.453 (2)0.498 (5)0.022 (6)0.040*0.06
H110.29130.60260.26670.025*0.94
H13A0.20710.29490.15060.026*0.94
H13B0.25170.09530.18850.026*0.94
H130.17890.04540.29530.040*0.94
H14A0.16360.41680.41860.027*0.94
H14B0.21980.56650.47020.027*0.94
H140.15460.61390.25170.038*0.94
H15A0.30370.26280.50110.030*0.94
H15B0.23550.15960.51120.030*0.94
H150.32720.00030.36320.043*0.94
H210.46080.38040.15700.024*0.94
H23A0.49930.88070.24420.025*0.94
H23B0.54570.68200.27350.025*0.94
H230.57001.03730.14210.039*0.94
H24A0.53190.42860.04900.027*0.94
H24B0.58730.57990.00450.027*0.94
H240.59800.37610.16730.038*0.94
H25A0.51390.83540.08350.028*0.94
H25B0.44530.73470.07200.028*0.94
H250.42460.99180.07220.040*0.94
H11B0.28980.89320.26310.048*0.06
H13C0.25231.40520.19310.060*0.06
H13D0.20931.20260.15280.060*0.06
H13E0.15211.48470.20940.060*0.06
H14C0.22340.92030.46830.060*0.06
H14D0.16641.07290.42490.060*0.06
H14E0.18600.71970.32790.060*0.06
H15C0.23871.33530.51520.060*0.06
H15D0.30771.23870.49920.060*0.06
H15E0.26531.57910.36440.060*0.06
H21B0.46191.09610.17520.048*0.06
H23C0.54270.80860.27570.060*0.06
H23D0.49850.60820.23810.060*0.06
H23E0.59720.51660.22530.060*0.06
H24C0.58640.92080.00250.048*0.06
H24D0.53021.07150.04700.048*0.06
H24E0.56371.28780.08670.060*0.06
H25C0.44510.77820.07040.060*0.06
H25D0.51240.66880.08430.060*0.06
H25E0.43570.51460.09650.060*0.06
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C110.0166 (14)0.0219 (15)0.0216 (16)0.0028 (11)0.0007 (13)0.0012 (14)
O110.0239 (13)0.0199 (10)0.0449 (19)0.0008 (9)0.0048 (15)0.0029 (13)
N110.0150 (12)0.0206 (12)0.0265 (16)0.0015 (9)0.0011 (11)0.0038 (13)
C120.0141 (14)0.0206 (15)0.0193 (17)0.0016 (11)0.0001 (12)0.0009 (14)
C130.0216 (17)0.0214 (14)0.0213 (19)0.0010 (14)0.0009 (15)0.0023 (15)
O130.0191 (10)0.0193 (10)0.0412 (15)0.0028 (8)0.0055 (11)0.0029 (12)
C140.0190 (15)0.0237 (16)0.0256 (19)0.0022 (12)0.0030 (14)0.0029 (14)
O140.0190 (11)0.0195 (10)0.0380 (16)0.0002 (8)0.0058 (11)0.0016 (11)
C150.0229 (17)0.0286 (18)0.023 (2)0.0012 (14)0.0033 (15)0.0051 (17)
O150.0241 (12)0.0253 (12)0.0367 (16)0.0020 (9)0.0025 (12)0.0091 (12)
C210.0172 (14)0.0218 (15)0.0216 (17)0.0019 (11)0.0032 (13)0.0015 (13)
O210.0203 (12)0.0226 (10)0.0356 (17)0.0014 (8)0.0106 (14)0.0050 (11)
N210.0169 (11)0.0204 (11)0.0233 (15)0.0013 (9)0.0032 (12)0.0019 (12)
C220.0142 (14)0.0207 (15)0.024 (2)0.0010 (12)0.0026 (13)0.0030 (15)
C230.0180 (16)0.0197 (15)0.026 (2)0.0012 (14)0.0006 (15)0.0008 (15)
O230.0200 (10)0.0183 (9)0.0389 (15)0.0044 (8)0.0052 (11)0.0052 (12)
C240.0200 (15)0.0239 (15)0.0232 (19)0.0010 (12)0.0007 (14)0.0004 (14)
O240.0186 (11)0.0188 (10)0.0381 (15)0.0003 (8)0.0053 (10)0.0012 (11)
C250.0208 (16)0.0262 (16)0.0239 (19)0.0000 (14)0.0009 (15)0.0025 (17)
O250.0212 (12)0.0235 (11)0.0356 (16)0.0002 (8)0.0015 (11)0.0066 (11)
Geometric parameters (Å, º) top
C11—O111.242 (4)C11B—O11B1.213 (4)
C11—N111.323 (4)C11B—N11B1.275 (5)
N11—C121.470 (4)C11B—C21B1.53 (2)
C11—C211.535 (4)N11B—C12B1.468 (19)
N11—H110.8800N11B—H11B0.8800
C12—C131.526 (5)C12B—C13B1.528 (19)
C12—C141.526 (4)C12B—C14B1.530 (19)
C12—C151.544 (4)C12B—C15B1.530 (19)
C13—O131.424 (4)C13B—O13B1.42 (2)
C13—H13A0.9900C13B—H13C0.9900
C13—H13B0.9900C13B—H13D0.9900
O13—H130.8400O13B—H13E0.8400
C14—O141.421 (4)C14B—O14B1.41 (2)
C14—H14A0.9900C14B—H14C0.9900
C14—H14B0.9900C14B—H14D0.9900
O14—H140.8400O14B—H14E0.8400
C15—O151.417 (4)C15B—O15B1.41 (2)
C15—H15A0.9900C15B—H15C0.9900
C15—H15B0.9900C15B—H15D0.9900
O15—H150.8400O15B—H15E0.8400
C21—O211.229 (3)C21B—O21B1.23 (4)
C21—N211.332 (4)C21B—N21B1.33 (2)
N21—C221.467 (4)N21B—C22B1.46 (2)
N21—H210.8800N21B—H21B0.8800
C22—C231.529 (5)C22B—C25B1.52 (2)
C22—C241.533 (4)C22B—C24B1.52 (2)
C22—C251.544 (5)C22B—C23B1.524 (19)
C23—O231.421 (4)C23B—O23B1.42 (2)
C23—H23A0.9900C23B—H23C0.9900
C23—H23B0.9900C23B—H23D0.9900
O23—H230.8400O23B—H23E0.8400
C24—O241.418 (4)C24B—O24B1.42 (2)
C24—H24A0.9900C24B—H24C0.9900
C24—H24B0.9900C24B—H24D0.9900
O24—H240.8400O24B—H24E0.8400
C25—O251.415 (4)C25B—O25B1.41 (2)
C25—H25A0.9900C25B—H25C0.9900
C25—H25B0.9900C25B—H25D0.9900
O25—H250.8400O25B—H25E0.8400
O11—C11—N11127.1 (3)C11B—N11B—C12B126.6 (11)
O11—C11—C21120.4 (3)C11B—N11B—H11B116.7
N11—C11—C21112.5 (2)C12B—N11B—H11B116.7
C11—N11—C12127.8 (3)N11B—C12B—C13B107 (3)
C11—N11—H11116.1N11B—C12B—C14B103 (3)
C12—N11—H11116.1C13B—C12B—C14B111.1 (17)
N11—C12—C13108.1 (3)N11B—C12B—C15B114 (3)
N11—C12—C14105.5 (2)C13B—C12B—C15B110.9 (17)
C13—C12—C14110.9 (3)C14B—C12B—C15B110.1 (17)
N11—C12—C15112.9 (2)O13B—C13B—C12B111.2 (19)
C13—C12—C15110.9 (2)O13B—C13B—H13C109.4
C14—C12—C15108.4 (3)C12B—C13B—H13C109.4
O13—C13—C12110.9 (3)O13B—C13B—H13D109.4
O13—C13—H13A109.5C12B—C13B—H13D109.4
C12—C13—H13A109.5H13C—C13B—H13D108.0
O13—C13—H13B109.5C13B—O13B—H13E109.5
C12—C13—H13B109.5O14B—C14B—C12B112 (2)
H13A—C13—H13B108.0O14B—C14B—H14C109.2
O14—C14—C12111.2 (3)C12B—C14B—H14C109.2
O14—C14—H14A109.4O14B—C14B—H14D109.2
C12—C14—H14A109.4C12B—C14B—H14D109.2
O14—C14—H14B109.4H14C—C14B—H14D107.9
C12—C14—H14B109.4C14B—O14B—H14E109.5
H14A—C14—H14B108.0O15B—C15B—C12B112 (2)
O15—C15—C12114.9 (3)O15B—C15B—H15C109.2
O15—C15—H15A108.5C12B—C15B—H15C109.2
C12—C15—H15A108.5O15B—C15B—H15D109.2
O15—C15—H15B108.5C12B—C15B—H15D109.2
C12—C15—H15B108.5H15C—C15B—H15D107.9
H15A—C15—H15B107.5C15B—O15B—H15E109.5
O21—C21—N21126.9 (3)O21B—C21B—N21B123 (3)
O21—C21—C11120.3 (3)O21B—C21B—C11B121 (3)
N21—C21—C11112.8 (2)N21B—C21B—C11B116 (3)
C21—N21—C22126.7 (2)C21B—N21B—C22B132 (4)
C21—N21—H21116.7C21B—N21B—H21B113.9
C22—N21—H21116.7C22B—N21B—H21B113.9
N21—C22—C23108.3 (3)N21B—C22B—C25B111 (4)
N21—C22—C24105.6 (2)N21B—C22B—C24B109 (3)
C23—C22—C24109.7 (3)C25B—C22B—C24B109 (3)
N21—C22—C25113.4 (2)N21B—C22B—C23B104 (4)
C23—C22—C25111.1 (2)C25B—C22B—C23B112.1 (16)
C24—C22—C25108.6 (3)C24B—C22B—C23B111.7 (18)
O23—C23—C22110.7 (3)O23B—C23B—C22B112 (2)
O23—C23—H23A109.5O23B—C23B—H23C109.2
C22—C23—H23A109.5C22B—C23B—H23C109.2
O23—C23—H23B109.5O23B—C23B—H23D109.2
C22—C23—H23B109.5C22B—C23B—H23D109.2
H23A—C23—H23B108.1H23C—C23B—H23D107.9
O24—C24—C22111.6 (3)C23B—O23B—H23E109.5
O24—C24—H24A109.3O24B—C24B—C22B114 (2)
C22—C24—H24A109.3O24B—C24B—H24C108.8
O24—C24—H24B109.3C22B—C24B—H24C108.8
C22—C24—H24B109.3O24B—C24B—H24D108.8
H24A—C24—H24B108.0C22B—C24B—H24D108.8
O25—C25—C22114.8 (3)H24C—C24B—H24D107.7
O25—C25—H25A108.6C24B—O24B—H24E109.5
C22—C25—H25A108.6O25B—C25B—C22B114 (2)
O25—C25—H25B108.6O25B—C25B—H25C108.7
C22—C25—H25B108.6C22B—C25B—H25C108.7
H25A—C25—H25B107.6O25B—C25B—H25D108.7
O11B—C11B—N11B127.2 (2)C22B—C25B—H25D108.7
O11B—C11B—C21B119.3 (17)H25C—C25B—H25D107.6
N11B—C11B—C21B113.5 (17)C25B—O25B—H25E109.5
C12—N11—C11—C21176.3 (3)O11B—C11B—N11B—C12B1 (2)
C12—N11—C11—O115.3 (6)C21B—C11B—N11B—C12B178 (3)
O11—C11—C21—O21179.8 (5)C11B—N11B—C12B—C13B79 (3)
C11—N11—C12—C1375.8 (4)C11B—N11B—C12B—C14B163.4 (18)
C11—N11—C12—C14165.4 (3)C11B—N11B—C12B—C15B44 (3)
C11—N11—C12—C1547.3 (5)N11B—C12B—C13B—O13B172 (4)
N11—C12—C13—O13175.4 (2)C14B—C12B—C13B—O13B60 (5)
C14—C12—C13—O1360.2 (3)C15B—C12B—C13B—O13B63 (5)
C15—C12—C13—O1360.3 (3)N11B—C12B—C14B—O14B52 (5)
N11—C12—C14—O1450.6 (4)C13B—C12B—C14B—O14B63 (5)
C13—C12—C14—O1466.3 (3)C15B—C12B—C14B—O14B174 (5)
C15—C12—C14—O14171.8 (2)N11B—C12B—C15B—O15B89 (5)
N11—C12—C15—O1586.3 (3)C13B—C12B—C15B—O15B33 (6)
C13—C12—C15—O1535.3 (4)C14B—C12B—C15B—O15B156 (5)
C14—C12—C15—O15157.3 (3)O11B—C11B—C21B—O21B176 (4)
C22—N21—C21—C11175.8 (3)N11B—C11B—C21B—O21B3 (6)
C22—N21—C21—O214.2 (6)O11B—C11B—C21B—N21B4 (6)
N11—C11—C21—N21178.8 (4)N11B—C11B—C21B—N21B177 (4)
N11—C11—C21—O211.2 (5)O21B—C21B—N21B—C22B1 (10)
O11—C11—C21—N210.3 (4)C11B—C21B—N21B—C22B179 (4)
C21—N21—C22—C2378.7 (4)C21B—N21B—C22B—C25B38 (7)
C21—N21—C22—C24163.8 (3)C21B—N21B—C22B—C24B158 (6)
C21—N21—C22—C2545.0 (4)C21B—N21B—C22B—C23B83 (6)
N21—C22—C23—O23176.5 (2)N21B—C22B—C23B—O23B177 (4)
C24—C22—C23—O2361.7 (3)C25B—C22B—C23B—O23B63 (6)
C25—C22—C23—O2358.4 (3)C24B—C22B—C23B—O23B59 (5)
N21—C22—C24—O2450.7 (3)N21B—C22B—C24B—O24B49 (6)
C23—C22—C24—O2465.8 (3)C25B—C22B—C24B—O24B171 (5)
C25—C22—C24—O24172.6 (2)C23B—C22B—C24B—O24B65 (6)
N21—C22—C25—O2587.9 (3)N21B—C22B—C25B—O25B82 (6)
C23—C22—C25—O2534.3 (4)C24B—C22B—C25B—O25B158 (5)
C24—C22—C25—O25155.1 (3)C23B—C22B—C25B—O25B34 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O13—H13···O14i0.841.852.652 (3)158
O14—H14···O23ii0.841.822.650 (3)167
O15—H15···O110.842.032.765 (4)146
O23—H23···O24iii0.841.842.658 (3)163
O24—H24···O13iv0.841.842.666 (3)171
O25—H25···O210.842.032.756 (4)144
Symmetry codes: (i) x, y1, z; (ii) x1/2, y+3/2, z; (iii) x, y+1, z; (iv) x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formulaC10H20N2O8
Mr296.28
Crystal system, space groupOrthorhombic, Pna21
Temperature (K)150
a, b, c (Å)21.4097 (3), 6.1559 (6), 10.0605 (13)
V3)1325.9 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.13
Crystal size (mm)0.30 × 0.10 × 0.10
Data collection
DiffractometerKappa-CCD
diffractometer
Absorption correctionMulti-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
Tmin, Tmax0.962, 0.987
No. of measured, independent and
observed [I > 2σ(I)] reflections
7853, 1573, 1282
Rint0.101
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.120, 1.02
No. of reflections1573
No. of parameters235
No. of restraints36
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.26, 0.28

Computer programs: Kappa-CCD Server Software (Nonius, 1997), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, SHELXS97 (Sheldrick, 1997), PLATON (Spek, 2001), SHELXL97 (Sheldrick, 1997) and PRPKAPPA (Ferguson, 1999).

Selected geometric parameters (Å, º) top
C11—O111.242 (4)C21—O211.229 (3)
C11—N111.323 (4)C21—N211.332 (4)
N11—C121.470 (4)N21—C221.467 (4)
C11—C211.535 (4)
O11—C11—N11127.1 (3)O21—C21—N21126.9 (3)
O11—C11—C21120.4 (3)O21—C21—C11120.3 (3)
N11—C11—C21112.5 (2)N21—C21—C11112.8 (2)
C11—N11—C12127.8 (3)C21—N21—C22126.7 (2)
C12—N11—C11—C21176.3 (3)C22—N21—C21—C11175.8 (3)
C12—N11—C11—O115.3 (6)C22—N21—C21—O214.2 (6)
O11—C11—C21—O21179.8 (5)N11—C11—C21—N21178.8 (4)
C11—N11—C12—C1375.8 (4)C21—N21—C22—C2378.7 (4)
C11—N11—C12—C14165.4 (3)C21—N21—C22—C24163.8 (3)
C11—N11—C12—C1547.3 (5)C21—N21—C22—C2545.0 (4)
N11—C12—C13—O13175.4 (2)N21—C22—C23—O23176.5 (2)
N11—C12—C14—O1450.6 (4)N21—C22—C24—O2450.7 (3)
N11—C12—C15—O1586.3 (3)N21—C22—C25—O2587.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O13—H13···O14i0.841.852.652 (3)158
O14—H14···O23ii0.841.822.650 (3)167
O15—H15···O110.842.032.765 (4)146
O23—H23···O24iii0.841.842.658 (3)163
O24—H24···O13iv0.841.842.666 (3)171
O25—H25···O210.842.032.756 (4)144
Symmetry codes: (i) x, y1, z; (ii) x1/2, y+3/2, z; (iii) x, y+1, z; (iv) x+1/2, y+1/2, z.
 

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