Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801011047/bt6057sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801011047/bt6057Isup2.hkl |
CCDC reference: 170891
Tris(2-aminoethylamine) (0.146 g, 1.00 mmol) and succinic anhydride (0.300 g, 3.00 mmol) were heated under reflux in benzene (70 ml) for 12 h. Upon cooling, colourless hexagonal crystals of the title compound were formed.
At convergence of a refinement model containing no hydration, a peak of 0.66 e Å-3 was observed, approximately three times the size of other peaks and troughs in the difference Fourier synthesis. This feature was modelled isotropically as the O atom of a partially occupied water molecule. However, its occupancy of the 3 site at (2/3,1/3,1/3) refined to only 0.15 (2), corresponding to a 0.075-hydrate. Water H atoms were not located; methylene H atoms were introduced at geometrically calculated positions and allowed to ride 0.98 Å from their parent atoms with Uiso(H) = 1.2Ueq(C).
Data collection: STADI-4 (Stoe & Cie, 1996); cell refinement: STADI-4; data reduction: X-RED (Stoe & Cie, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2001); software used to prepare material for publication: SHELXL97 and PLATON.
C18H24N4O6·0.075H2O | Dx = 1.376 Mg m−3 |
Mr = 393.67 | Mo Kα radiation, λ = 0.71073 Å |
Trigonal, R3 | Cell parameters from 29 reflections |
a = 13.200 (2) Å | θ = 25.1–29.6° |
c = 18.874 (5) Å | µ = 0.11 mm−1 |
V = 2848.0 (10) Å3 | T = 210 K |
Z = 6 | Hexagonal plate, colourless |
F(000) = 1251 | 0.39 × 0.32 × 0.06 mm |
Stoe Stadi-4 four-circle diffractometer | Rint = 0.137 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 2.1° |
Graphite monochromator | h = −15→15 |
ω/θ scans | k = −7→15 |
1343 measured reflections | l = 0→22 |
1128 independent reflections | 3 standard reflections every 60 min |
738 reflections with I > 2σ(I) | intensity decay: none |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.071 | Calculated w = 1/[σ2(Fo2) + (0.023P)2 + 9.981P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.144 | (Δ/σ)max = 0.001 |
S = 1.28 | Δρmax = 0.23 e Å−3 |
1128 reflections | Δρmin = −0.20 e Å−3 |
86 parameters | Extinction correction: SHELXL97 |
0 restraints | Extinction coefficient: none |
Primary atom site location: structure-invariant direct methods |
C18H24N4O6·0.075H2O | Z = 6 |
Mr = 393.67 | Mo Kα radiation |
Trigonal, R3 | µ = 0.11 mm−1 |
a = 13.200 (2) Å | T = 210 K |
c = 18.874 (5) Å | 0.39 × 0.32 × 0.06 mm |
V = 2848.0 (10) Å3 |
Stoe Stadi-4 four-circle diffractometer | Rint = 0.137 |
1343 measured reflections | 3 standard reflections every 60 min |
1128 independent reflections | intensity decay: none |
738 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.071 | 0 restraints |
wR(F2) = 0.144 | H-atom parameters constrained |
S = 1.28 | Δρmax = 0.23 e Å−3 |
1128 reflections | Δρmin = −0.20 e Å−3 |
86 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N | 0.6667 | 0.3333 | 0.1103 (3) | 0.0243 (12) | |
C1 | 0.7327 (3) | 0.4542 (3) | 0.13715 (19) | 0.0278 (9) | |
H1A | 0.7475 | 0.4519 | 0.1878 | 0.033* | |
H1B | 0.6841 | 0.4907 | 0.1320 | 0.033* | |
C2 | 0.8483 (3) | 0.5302 (3) | 0.10021 (19) | 0.0312 (10) | |
H2A | 0.8935 | 0.6022 | 0.1276 | 0.037* | |
H2B | 0.8926 | 0.4889 | 0.0995 | 0.037* | |
N3 | 0.8358 (3) | 0.5608 (3) | 0.02792 (15) | 0.0252 (8) | |
C4 | 0.8483 (3) | 0.5087 (3) | −0.0324 (2) | 0.0312 (10) | |
O4 | 0.8693 (3) | 0.4293 (3) | −0.03229 (16) | 0.0481 (9) | |
C5 | 0.8325 (4) | 0.5687 (4) | −0.0957 (2) | 0.0371 (10) | |
H5A | 0.7677 | 0.5124 | −0.1253 | 0.045* | |
H5B | 0.9039 | 0.6060 | −0.1244 | 0.045* | |
C6 | 0.8059 (4) | 0.6595 (4) | −0.0659 (2) | 0.0336 (10) | |
H6A | 0.8649 | 0.7382 | −0.0811 | 0.040* | |
H6B | 0.7287 | 0.6443 | −0.0815 | 0.040* | |
C7 | 0.8088 (3) | 0.6474 (3) | 0.0129 (2) | 0.0307 (9) | |
O7 | 0.7909 (3) | 0.7015 (3) | 0.05829 (15) | 0.0442 (9) | |
O1W | 0.6667 | 0.3333 | 0.3333 | 0.08 (3)* | 0.15 |
U11 | U22 | U33 | U12 | U13 | U23 | |
N | 0.0255 (18) | 0.0255 (18) | 0.022 (3) | 0.0128 (9) | 0.000 | 0.000 |
C1 | 0.031 (2) | 0.028 (2) | 0.025 (2) | 0.0145 (18) | 0.0005 (17) | −0.0033 (17) |
C2 | 0.030 (2) | 0.031 (2) | 0.031 (2) | 0.0130 (19) | −0.0047 (18) | 0.0020 (18) |
N3 | 0.0265 (18) | 0.0225 (17) | 0.0245 (17) | 0.0107 (14) | −0.0005 (14) | 0.0003 (14) |
C4 | 0.021 (2) | 0.029 (2) | 0.038 (2) | 0.0079 (17) | 0.0009 (17) | −0.0076 (18) |
O4 | 0.058 (2) | 0.0395 (18) | 0.058 (2) | 0.0326 (17) | 0.0079 (17) | −0.0028 (16) |
C5 | 0.036 (2) | 0.044 (3) | 0.032 (2) | 0.020 (2) | −0.003 (2) | −0.001 (2) |
C6 | 0.031 (2) | 0.033 (2) | 0.035 (2) | 0.015 (2) | −0.0010 (18) | 0.0086 (19) |
C7 | 0.026 (2) | 0.023 (2) | 0.040 (2) | 0.0103 (18) | −0.0011 (18) | −0.0014 (18) |
O7 | 0.058 (2) | 0.0383 (18) | 0.0453 (19) | 0.0312 (17) | −0.0014 (15) | −0.0080 (15) |
N—C1i | 1.474 (4) | C6—C7 | 1.499 (5) |
N—C1 | 1.474 (4) | C7—O7 | 1.211 (5) |
N—C1ii | 1.474 (4) | C1—H1A | 0.9800 |
C1—C2 | 1.513 (5) | C1—H1B | 0.9800 |
C2—N3 | 1.455 (4) | C2—H2A | 0.9800 |
N3—C4 | 1.381 (5) | C2—H2B | 0.9800 |
N3—C7 | 1.387 (5) | C5—H5A | 0.9800 |
C4—O4 | 1.210 (5) | C5—H5B | 0.9800 |
C4—C5 | 1.505 (5) | C6—H6A | 0.9800 |
C5—C6 | 1.515 (5) | C6—H6B | 0.9800 |
C1i—N—C1 | 108.9 (2) | N—C1—H1B | 108.6 |
C1i—N—C1ii | 108.9 (2) | C2—C1—H1B | 108.7 |
C1—N—C1ii | 108.9 (2) | H1A—C1—H1B | 107.6 |
N—C1—C2 | 114.4 (3) | N3—C2—H2A | 108.8 |
N3—C2—C1 | 113.6 (3) | C1—C2—H2A | 108.8 |
C4—N3—C7 | 112.7 (3) | N3—C2—H2B | 108.9 |
C4—N3—C2 | 125.2 (3) | C1—C2—H2B | 108.9 |
C7—N3—C2 | 122.1 (3) | H2A—C2—H2B | 107.7 |
O4—C4—N3 | 124.4 (4) | C4—C5—H5A | 110.6 |
O4—C4—C5 | 127.5 (4) | C6—C5—H5A | 110.6 |
N3—C4—C5 | 108.0 (3) | C4—C5—H5B | 110.6 |
C4—C5—C6 | 105.7 (3) | C6—C5—H5B | 110.6 |
C7—C6—C5 | 104.8 (3) | H5A—C5—H5B | 108.7 |
O7—C7—N3 | 123.2 (4) | C7—C6—H6A | 110.8 |
O7—C7—C6 | 128.0 (4) | C5—C6—H6A | 110.8 |
N3—C7—C6 | 108.7 (3) | C7—C6—H6B | 110.8 |
N—C1—H1A | 108.6 | C5—C6—H6B | 110.8 |
C2—C1—H1A | 108.7 | H6A—C6—H6B | 108.9 |
C1i—N—C1—C2 | 75.6 (5) | O4—C4—C5—C6 | 179.0 (4) |
C1ii—N—C1—C2 | −165.9 (3) | N3—C4—C5—C6 | −1.5 (4) |
N—C1—C2—N3 | 70.8 (4) | C4—C5—C6—C7 | 0.4 (4) |
C1—C2—N3—C4 | −101.7 (4) | C4—N3—C7—O7 | 177.9 (4) |
C1—C2—N3—C7 | 77.9 (5) | C2—N3—C7—O7 | −1.8 (6) |
C7—N3—C4—O4 | −178.3 (4) | C4—N3—C7—C6 | −2.0 (4) |
C2—N3—C4—O4 | 1.4 (6) | C2—N3—C7—C6 | 178.4 (3) |
C7—N3—C4—C5 | 2.2 (4) | C5—C6—C7—O7 | −179.0 (4) |
C2—N3—C4—C5 | −178.1 (3) | C5—C6—C7—N3 | 0.9 (4) |
Symmetry codes: (i) −x+y+1, −x+1, z; (ii) −y+1, x−y, z. |
Experimental details
Crystal data | |
Chemical formula | C18H24N4O6·0.075H2O |
Mr | 393.67 |
Crystal system, space group | Trigonal, R3 |
Temperature (K) | 210 |
a, c (Å) | 13.200 (2), 18.874 (5) |
V (Å3) | 2848.0 (10) |
Z | 6 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.39 × 0.32 × 0.06 |
Data collection | |
Diffractometer | Stoe Stadi-4 four-circle diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 1343, 1128, 738 |
Rint | 0.137 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.071, 0.144, 1.28 |
No. of reflections | 1128 |
No. of parameters | 86 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.23, −0.20 |
Computer programs: STADI-4 (Stoe & Cie, 1996), STADI-4, X-RED (Stoe & Cie, 1996), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2001), SHELXL97 and PLATON.
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