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The title compound, (HOCH2CH2)2NC(CH2OH)3 or C8H19NO5, is an important complexing agent. All hydroxyl-H atoms are involved in intermolecular hydrogen bonds (O—H...O distances are in the range 2.690–2.847 Å), which link the mol­ecules in the crystal into a three-dimensional infinite network. One of the hydroxy­methyl hydroxyl groups also participates in an intramolecular O—H...N hydrogen bond, closing a five-membered N—C—C—O—H pseudo-cycle [O...N 2.7804 (16) Å and O—H...N 118.6 (17)°].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801017974/ya6068sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801017974/ya6068Isup2.hkl
Contains datablock I

CCDC reference: 176047

Key indicators

  • Single-crystal X-ray study
  • T = 203 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.034
  • wR factor = 0.084
  • Data-to-parameter ratio = 11.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
ABSMU_01 Alert C The ratio of given/expected absorption coefficient lies outside the range 0.99 <> 1.01 Calculated value of mu = 0.115 Value of mu given = 0.120
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Comment top

The title compound, (I), commonly called Bis-Tris, is an important polyalcohol used in the complexation of metal ions (Hong et al., 1995; Sigel et al., 1982; Scheller et al., 1980; Wesolowski & Palmer, 1989; Wesolowski et al., 1990). It has received special attention as a chelation agent for some lanthanide ions (Oh et al., 1998; Chen et al., 1997; Pfefferle & Bunzli, 1989). The structure of (I) was determined in the course of an ongoing investigation into the complexation properties of Bis-Tris with various lanthanide halides (Wood et al., 2000).

All five hydroxyl-H atoms in (I) (Fig. 1) are involved in intermolecular hydrogen bonds (Table 1), which link the molecules in the crystal of (I) into a three-dimensional infinite network. Fig. 2 shows the three-dimensional network down [010]. It can be seen from this direction that the hydrogen bonding is localized in regular supramolecular synthons (Desiraju & Steiner, 2001). One of these synthons is shown in Fig. 3 and Fig. 4.

The O3—H3 hydroxyl group also serves as a donor for an intramolecular O3—H3···N1 bond (see Table 1), thus giving rise to a bifurcated hydrogen bond and closing the five-membered N1—C1—C4—O3—H3 pseudo-cycle. There are two other possibilities for intramolecular hydrogen bonding in (I). However, the C4—H4B···O1 and C5—H5B···O2 interactions should in fact be classified as extremely weak, if existing at all. As these are not bifurcated, it appears that this bonding is geometrically unlikely in the former, and extremely weak in the latter case. The corresponding distances and angles, are, nevertheless, included in Table 1 for comparison.

Experimental top

The title compound was obtained commercially (Aldrich) and crystallized from a concentrated methanol solution.

Refinement top

All hydroxyl-H atoms were located and refined (O—H 0.78–0.84 Å). All the rest of the H atoms were placed geometrically and included in the refinement in the riding-motion approximation with displacement parameters equal to 1.2Ueq of the corresponding carrier atom.

Computing details top

Data collection: SMART (Bruker, 1997–1998); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 1999); program(s) used to solve structure: XS in SHELXTL (Sheldrick, 1998); program(s) used to refine structure: XL in SHELXTL; molecular graphics: XP in SHELXTL; software used to prepare material for publication: XCIF in SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with atom labels and 30% probability ellipsoids for non-H atoms.
[Figure 2] Fig. 2. A view down [010] showing the extensive hydrogen bonding. Intermolecular interactions are indicated by dashed lines. Only H atoms involved in intermolecular interactions are shown.
[Figure 3] Fig. 3. A view of the hydrogen-bonding synthon parallel to the [010] direction. Only O and H atoms involved in hydrogen bonding are shown. O atoms are shown with 30% probability ellipsoids.
[Figure 4] Fig. 4. The hydrogen-bonding synthon viewed down [010]. Only O and H atoms involved in hydrogen bonding are shown. O atoms are shown with 30% probability ellipsoids.
(I) top
Crystal data top
C8H19NO5Dx = 1.403 Mg m3
Mr = 209.24Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 1001 reflections
a = 12.1298 (17) Åθ = 2.4–27.9°
b = 9.5303 (13) ŵ = 0.12 mm1
c = 17.144 (2) ÅT = 203 K
V = 1981.9 (5) Å3Needle, colorless
Z = 80.32 × 0.20 × 0.11 mm
F(000) = 912
Data collection top
Siemens SMART 1K
diffractometer
1745 independent reflections
Radiation source: normal-focus sealed tube1476 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
Detector resolution: 8.3 pixels mm-1θmax = 25.0°, θmin = 2.9°
ω scansh = 1411
Absorption correction: empirical
(SADABS; Sheldrick, 1999)
k = 1111
Tmin = 0.964, Tmax = 0.987l = 2016
14160 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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0399P)2 + 0.7334P]
where P = (Fo2 + 2Fc2)/3
1745 reflections(Δ/σ)max < 0.001
147 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.18 e Å3
Crystal data top
C8H19NO5V = 1981.9 (5) Å3
Mr = 209.24Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 12.1298 (17) ŵ = 0.12 mm1
b = 9.5303 (13) ÅT = 203 K
c = 17.144 (2) Å0.32 × 0.20 × 0.11 mm
Data collection top
Siemens SMART 1K
diffractometer
1745 independent reflections
Absorption correction: empirical
(SADABS; Sheldrick, 1999)
1476 reflections with I > 2σ(I)
Tmin = 0.964, Tmax = 0.987Rint = 0.033
14160 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.084H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.24 e Å3
1745 reflectionsΔρmin = 0.18 e Å3
147 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*/Ueq
N10.46638 (9)0.21083 (11)0.65075 (7)0.0200 (3)
O10.58293 (9)0.25164 (11)0.45071 (6)0.0273 (3)
O20.66745 (9)0.04041 (11)0.59010 (7)0.0323 (3)
O30.46313 (10)0.48513 (12)0.59555 (7)0.0355 (3)
O40.26258 (9)0.07991 (11)0.62309 (7)0.0305 (3)
O50.34000 (10)0.38224 (12)0.76953 (7)0.0356 (3)
C10.55049 (11)0.25295 (14)0.59206 (8)0.0208 (3)
C20.50554 (12)0.21767 (14)0.51044 (8)0.0226 (3)
H2A0.48820.11730.50790.027*
H2B0.43710.27000.50160.027*
C30.66468 (12)0.18757 (15)0.60385 (9)0.0262 (3)
H3A0.71700.23350.56860.031*
H3B0.68890.20580.65740.031*
C40.56531 (12)0.41289 (14)0.59709 (9)0.0249 (3)
H4A0.60430.43620.64540.030*
H4B0.61080.44460.55320.030*
C50.42278 (12)0.06642 (14)0.64419 (8)0.0213 (3)
H5A0.42800.02060.69520.026*
H5B0.46890.01350.60770.026*
C60.30439 (12)0.06033 (15)0.61667 (9)0.0261 (3)
H6A0.25920.12380.64830.031*
H6B0.30020.09130.56220.031*
C70.49955 (12)0.23876 (16)0.73229 (8)0.0263 (4)
H7A0.54520.32360.73390.032*
H7B0.54420.16030.75140.032*
C80.40143 (13)0.25798 (15)0.78508 (9)0.0288 (4)
H8A0.35260.17670.77950.035*
H8B0.42700.26050.83930.035*
H50.3126 (16)0.378 (2)0.7262 (12)0.043 (6)*
H40.3020 (18)0.132 (2)0.5985 (12)0.052 (6)*
H10.5710 (16)0.334 (2)0.4361 (11)0.045 (5)*
H20.6681 (16)0.000 (2)0.6319 (13)0.052 (6)*
H30.4167 (17)0.433 (2)0.6077 (11)0.039 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0210 (6)0.0191 (6)0.0200 (6)0.0019 (5)0.0000 (5)0.0010 (5)
O10.0353 (6)0.0212 (5)0.0254 (6)0.0043 (5)0.0094 (5)0.0029 (4)
O20.0321 (6)0.0276 (6)0.0371 (7)0.0089 (5)0.0037 (5)0.0041 (5)
O30.0314 (7)0.0196 (6)0.0556 (8)0.0025 (5)0.0140 (6)0.0083 (5)
O40.0257 (6)0.0201 (5)0.0457 (7)0.0051 (4)0.0103 (5)0.0054 (5)
O50.0493 (8)0.0316 (6)0.0259 (7)0.0111 (5)0.0004 (6)0.0042 (5)
C10.0205 (7)0.0194 (7)0.0223 (8)0.0014 (6)0.0007 (6)0.0001 (5)
C20.0248 (8)0.0199 (7)0.0232 (8)0.0012 (6)0.0018 (6)0.0007 (6)
C30.0211 (8)0.0278 (8)0.0297 (8)0.0005 (6)0.0008 (6)0.0015 (6)
C40.0253 (8)0.0218 (7)0.0275 (8)0.0020 (6)0.0018 (6)0.0016 (6)
C50.0233 (8)0.0177 (7)0.0230 (7)0.0004 (6)0.0015 (6)0.0018 (5)
C60.0227 (8)0.0190 (7)0.0368 (9)0.0031 (6)0.0013 (7)0.0012 (6)
C70.0292 (8)0.0288 (8)0.0210 (8)0.0021 (6)0.0029 (6)0.0010 (6)
C80.0370 (9)0.0274 (8)0.0220 (8)0.0028 (7)0.0010 (7)0.0007 (6)
Geometric parameters (Å, º) top
N1—C51.4787 (17)C2—H2A0.9800
N1—C71.4788 (18)C2—H2B0.9800
N1—C11.4881 (18)C3—H3A0.9800
O1—C21.4264 (18)C3—H3B0.9800
O1—H10.84 (2)C4—H4A0.9800
O2—C31.4225 (18)C4—H4B0.9800
O2—H20.81 (2)C5—C61.513 (2)
O3—C41.4179 (19)C5—H5A0.9800
O3—H30.78 (2)C5—H5B0.9800
O4—C61.4338 (17)C6—H6A0.9800
O4—H40.81 (2)C6—H6B0.9800
O5—C81.4243 (18)C7—C81.506 (2)
O5—H50.82 (2)C7—H7A0.9800
C1—C31.5322 (19)C7—H7B0.9800
C1—C41.5373 (19)C8—H8A0.9800
C1—C21.539 (2)C8—H8B0.9800
C5—N1—C7109.67 (11)C1—C4—H4A109.2
C5—N1—C1116.41 (11)O3—C4—H4B109.2
C7—N1—C1113.84 (11)C1—C4—H4B109.2
C2—O1—H1108.3 (13)H4A—C4—H4B107.9
C3—O2—H2108.8 (15)N1—C5—C6113.51 (11)
C4—O3—H3108.4 (14)N1—C5—H5A108.9
C6—O4—H4108.7 (15)C6—C5—H5A108.9
C8—O5—H5110.2 (14)N1—C5—H5B108.9
N1—C1—C3114.89 (11)C6—C5—H5B108.9
N1—C1—C4108.04 (11)H5A—C5—H5B107.7
C3—C1—C4106.86 (11)O4—C6—C5110.34 (12)
N1—C1—C2108.24 (11)O4—C6—H6A109.6
C3—C1—C2110.57 (11)C5—C6—H6A109.6
C4—C1—C2108.00 (11)O4—C6—H6B109.6
O1—C2—C1111.72 (12)C5—C6—H6B109.6
O1—C2—H2A109.3H6A—C6—H6B108.1
C1—C2—H2A109.3N1—C7—C8112.02 (12)
O1—C2—H2B109.3N1—C7—H7A109.2
C1—C2—H2B109.3C8—C7—H7A109.2
H2A—C2—H2B107.9N1—C7—H7B109.2
O2—C3—C1113.60 (12)C8—C7—H7B109.2
O2—C3—H3A108.8H7A—C7—H7B107.9
C1—C3—H3A108.8O5—C8—C7113.71 (13)
O2—C3—H3B108.8O5—C8—H8A108.8
C1—C3—H3B108.8C7—C8—H8A108.8
H3A—C3—H3B107.7O5—C8—H8B108.8
O3—C4—C1112.22 (12)C7—C8—H8B108.8
O3—C4—H4A109.2H8A—C8—H8B107.7
C5—N1—C1—C373.38 (15)C2—C1—C3—O254.49 (15)
C7—N1—C1—C355.70 (15)N1—C1—C4—O349.41 (15)
C5—N1—C1—C4167.44 (11)C3—C1—C4—O3173.55 (12)
C7—N1—C1—C463.47 (14)C2—C1—C4—O367.47 (15)
C5—N1—C1—C250.73 (14)C7—N1—C5—C6119.55 (13)
C7—N1—C1—C2179.81 (11)C1—N1—C5—C6109.40 (14)
N1—C1—C2—O1178.45 (10)N1—C5—C6—O4171.18 (11)
C3—C1—C2—O151.79 (15)C5—N1—C7—C873.36 (15)
C4—C1—C2—O164.81 (15)C1—N1—C7—C8154.22 (12)
N1—C1—C3—O268.38 (16)N1—C7—C8—O567.83 (16)
C4—C1—C3—O2171.79 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O3i0.84 (2)1.86 (2)2.6897 (16)177 (2)
O2—H2···O5ii0.81 (2)2.03 (2)2.8410 (17)174 (2)
O3—H3···N10.78 (2)2.321 (19)2.7804 (16)118.6 (17)
O3—H3···O4iii0.78 (2)2.19 (2)2.8466 (17)141.6 (18)
O4—H4···O1iv0.81 (2)1.99 (2)2.7913 (16)171 (2)
O5—H5···O4iii0.82 (2)2.03 (2)2.8251 (17)165.6 (19)
C4—H4B···O10.982.572.9505 (18)103
C5—H5B···O20.982.443.1192 (18)126
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y1/2, z+3/2; (iii) x+1/2, y+1/2, z; (iv) x+1, y, z+1.

Experimental details

Crystal data
Chemical formulaC8H19NO5
Mr209.24
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)203
a, b, c (Å)12.1298 (17), 9.5303 (13), 17.144 (2)
V3)1981.9 (5)
Z8
Radiation typeMo Kα
µ (mm1)0.12
Crystal size (mm)0.32 × 0.20 × 0.11
Data collection
DiffractometerSiemens SMART 1K
diffractometer
Absorption correctionEmpirical
(SADABS; Sheldrick, 1999)
Tmin, Tmax0.964, 0.987
No. of measured, independent and
observed [I > 2σ(I)] reflections
14160, 1745, 1476
Rint0.033
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.084, 1.03
No. of reflections1745
No. of parameters147
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.24, 0.18

Computer programs: SMART (Bruker, 1997–1998), SMART, SAINT-Plus (Bruker, 1999), XS in SHELXTL (Sheldrick, 1998), XL in SHELXTL, XP in SHELXTL, XCIF in SHELXTL.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O3i0.84 (2)1.86 (2)2.6897 (16)177 (2)
O2—H2···O5ii0.81 (2)2.03 (2)2.8410 (17)174 (2)
O3—H3···N10.78 (2)2.321 (19)2.7804 (16)118.6 (17)
O3—H3···O4iii0.78 (2)2.19 (2)2.8466 (17)141.6 (18)
O4—H4···O1iv0.81 (2)1.99 (2)2.7913 (16)171 (2)
O5—H5···O4iii0.82 (2)2.03 (2)2.8251 (17)165.6 (19)
C4—H4B···O10.982.572.9505 (18)103.3
C5—H5B···O20.982.443.1192 (18)126.1
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y1/2, z+3/2; (iii) x+1/2, y+1/2, z; (iv) x+1, y, z+1.
 

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