Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801021432/na6117sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801021432/na6117Isup2.hkl |
CCDC reference: 180557
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.002 Å
- R factor = 0.034
- wR factor = 0.087
- Data-to-parameter ratio = 18.1
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
The title compound crystallized as a result of an attempted reaction between 2-aminomethyl-15-crown[5] and N3P3Cl6 in tetrahydrofuran solvent.
All H atoms approximate isotropic behaviour. The H atoms on the crown ether were placed in idealized positions with their displacement parameters riding on the value of the parent atom, whilst the water H atoms were experimentally located and allowed to freely refine.
Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1990).
Fig. 1. The molecular structure of (I) (50% probability displacement ellipsoids). | |
Fig. 2. The supramolecular array formed by (I) |
C11H24NO5+·Cl−·2H2O | F(000) = 1392 |
Mr = 321.79 | Dx = 1.356 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 21.4218 (4) Å | Cell parameters from 11239 reflections |
b = 7.8864 (2) Å | θ = 2.9–27.5° |
c = 19.7794 (4) Å | µ = 0.27 mm−1 |
β = 109.328 (1)° | T = 120 K |
V = 3153.22 (12) Å3 | Rod, colourless |
Z = 8 | 0.24 × 0.1 × 0.04 mm |
Nonius KappaCCD diffractometer | Rint = 0.051 |
Absorption correction: multi-scan (Blessing, 1997) | θmax = 27.5°, θmin = 3.1° |
Tmin = 0.938, Tmax = 0.989 | h = −27→25 |
14261 measured reflections | k = −10→10 |
3595 independent reflections | l = −25→25 |
3010 reflections with I > 2σ(I) |
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0345P)2 + 1.8513P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.034 | (Δ/σ)max = 0.003 |
wR(F2) = 0.087 | Δρmax = 0.27 e Å−3 |
S = 1.04 | Δρmin = −0.31 e Å−3 |
3595 reflections | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
199 parameters | Extinction coefficient: 0.0021 (4) |
0 restraints |
C11H24NO5+·Cl−·2H2O | V = 3153.22 (12) Å3 |
Mr = 321.79 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 21.4218 (4) Å | µ = 0.27 mm−1 |
b = 7.8864 (2) Å | T = 120 K |
c = 19.7794 (4) Å | 0.24 × 0.1 × 0.04 mm |
β = 109.328 (1)° |
Nonius KappaCCD diffractometer | 3595 independent reflections |
Absorption correction: multi-scan (Blessing, 1997) | 3010 reflections with I > 2σ(I) |
Tmin = 0.938, Tmax = 0.989 | Rint = 0.051 |
14261 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 0 restraints |
wR(F2) = 0.087 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.27 e Å−3 |
3595 reflections | Δρmin = −0.31 e Å−3 |
199 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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.30886 (6) | 0.17509 (16) | 0.09757 (7) | 0.0173 (3) | |
H1A | 0.3435 | 0.1147 | 0.1359 | 0.021* | |
H1B | 0.3038 | 0.1173 | 0.0516 | 0.021* | |
C2 | 0.24415 (6) | 0.16587 (16) | 0.11262 (7) | 0.0170 (3) | |
H2 | 0.2513 | 0.2096 | 0.1621 | 0.02* | |
C3 | 0.14096 (7) | 0.31623 (18) | 0.08214 (7) | 0.0223 (3) | |
H3A | 0.139 | 0.4408 | 0.0873 | 0.027* | |
H3B | 0.1457 | 0.2645 | 0.1292 | 0.027* | |
C4 | 0.07758 (7) | 0.25573 (18) | 0.02785 (8) | 0.0247 (3) | |
H4A | 0.0807 | 0.1329 | 0.0191 | 0.03* | |
H4B | 0.0404 | 0.2735 | 0.0463 | 0.03* | |
C5 | −0.00063 (7) | 0.3317 (2) | −0.08588 (9) | 0.0326 (4) | |
H5A | −0.0249 | 0.4389 | −0.0866 | 0.039* | |
H5B | −0.0239 | 0.2397 | −0.0699 | 0.039* | |
C6 | 0.00088 (7) | 0.29333 (18) | −0.15974 (8) | 0.0268 (3) | |
H6A | −0.045 | 0.2875 | −0.1936 | 0.032* | |
H6B | 0.024 | 0.3862 | −0.1755 | 0.032* | |
C7 | −0.00547 (7) | −0.01042 (18) | −0.16194 (7) | 0.0226 (3) | |
H7A | −0.0393 | −0.025 | −0.2098 | 0.027* | |
H7B | −0.0283 | 0.0016 | −0.1261 | 0.027* | |
C8 | 0.03988 (7) | −0.16048 (17) | −0.14426 (7) | 0.0222 (3) | |
H8A | 0.014 | −0.2666 | −0.1498 | 0.027* | |
H8B | 0.0665 | −0.1652 | −0.1767 | 0.027* | |
C9 | 0.13480 (7) | −0.26121 (16) | −0.05208 (7) | 0.0199 (3) | |
H9A | 0.1639 | −0.2439 | −0.0814 | 0.024* | |
H9B | 0.1169 | −0.378 | −0.0603 | 0.024* | |
C10 | 0.17320 (7) | −0.23633 (16) | 0.02545 (7) | 0.0199 (3) | |
H10A | 0.1431 | −0.2439 | 0.054 | 0.024* | |
H10B | 0.207 | −0.3266 | 0.0419 | 0.024* | |
C11 | 0.21955 (7) | −0.01537 (16) | 0.10792 (7) | 0.0187 (3) | |
H11A | 0.2539 | −0.0883 | 0.1409 | 0.022* | |
H11B | 0.1793 | −0.0208 | 0.122 | 0.022* | |
N1 | 0.33014 (5) | 0.35389 (13) | 0.09364 (6) | 0.0170 (2) | |
H1C | 0.31 | 0.395 | 0.0487 | 0.025* | |
H1D | 0.3748 | 0.3574 | 0.104 | 0.025* | |
H1E | 0.3186 | 0.4183 | 0.1258 | 0.025* | |
O1 | 0.19772 (4) | 0.27369 (11) | 0.06217 (5) | 0.0180 (2) | |
O2 | 0.06582 (5) | 0.34680 (13) | −0.03706 (5) | 0.0270 (2) | |
O3 | 0.03378 (4) | 0.13671 (12) | −0.16135 (5) | 0.0205 (2) | |
O4 | 0.08209 (4) | −0.14146 (11) | −0.07181 (5) | 0.0199 (2) | |
O5 | 0.20482 (4) | −0.07377 (11) | 0.03598 (5) | 0.0179 (2) | |
O6 | 0.16461 (5) | 0.68622 (15) | 0.20050 (6) | 0.0262 (2) | |
O7 | 0.39466 (6) | 0.91279 (16) | 0.24963 (7) | 0.0366 (3) | |
Cl1 | 0.310005 (16) | 0.55870 (4) | 0.222423 (17) | 0.02295 (12) | |
H04 | 0.3718 (10) | 0.995 (3) | 0.2649 (10) | 0.048 (5)* | |
H02 | 0.1684 (10) | 0.783 (3) | 0.2185 (10) | 0.042 (5)* | |
H03 | 0.3697 (11) | 0.820 (3) | 0.2448 (11) | 0.055 (6)* | |
H01 | 0.2037 (12) | 0.654 (3) | 0.2054 (11) | 0.054 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0195 (6) | 0.0152 (6) | 0.0176 (6) | −0.0013 (5) | 0.0065 (5) | 0.0006 (5) |
C2 | 0.0194 (6) | 0.0187 (6) | 0.0127 (6) | −0.0012 (5) | 0.0050 (5) | 0.0006 (5) |
C3 | 0.0266 (7) | 0.0220 (7) | 0.0238 (7) | 0.0027 (6) | 0.0158 (6) | −0.0001 (5) |
C4 | 0.0226 (7) | 0.0192 (7) | 0.0382 (8) | −0.0005 (5) | 0.0181 (6) | −0.0013 (6) |
C5 | 0.0158 (7) | 0.0351 (9) | 0.0446 (9) | 0.0029 (6) | 0.0070 (6) | −0.0132 (7) |
C6 | 0.0200 (7) | 0.0219 (7) | 0.0328 (8) | 0.0061 (6) | 0.0010 (6) | 0.0024 (6) |
C7 | 0.0171 (7) | 0.0238 (7) | 0.0252 (7) | −0.0037 (6) | 0.0049 (5) | −0.0029 (5) |
C8 | 0.0227 (7) | 0.0209 (7) | 0.0205 (7) | −0.0034 (5) | 0.0038 (6) | −0.0046 (5) |
C9 | 0.0196 (7) | 0.0139 (6) | 0.0264 (7) | 0.0001 (5) | 0.0079 (6) | −0.0021 (5) |
C10 | 0.0212 (7) | 0.0138 (6) | 0.0245 (7) | −0.0022 (5) | 0.0073 (6) | 0.0013 (5) |
C11 | 0.0206 (6) | 0.0203 (7) | 0.0149 (6) | −0.0029 (5) | 0.0056 (5) | 0.0013 (5) |
N1 | 0.0155 (5) | 0.0175 (6) | 0.0183 (6) | −0.0019 (4) | 0.0063 (4) | −0.0007 (4) |
O1 | 0.0180 (5) | 0.0199 (5) | 0.0184 (5) | 0.0026 (4) | 0.0092 (4) | 0.0030 (3) |
O2 | 0.0189 (5) | 0.0344 (6) | 0.0272 (5) | −0.0060 (4) | 0.0071 (4) | −0.0029 (4) |
O3 | 0.0167 (5) | 0.0190 (5) | 0.0247 (5) | 0.0004 (4) | 0.0053 (4) | 0.0004 (4) |
O4 | 0.0198 (5) | 0.0183 (5) | 0.0195 (5) | 0.0026 (4) | 0.0037 (4) | −0.0028 (4) |
O5 | 0.0226 (5) | 0.0158 (5) | 0.0158 (4) | −0.0054 (4) | 0.0070 (4) | −0.0011 (3) |
O6 | 0.0243 (6) | 0.0243 (6) | 0.0300 (6) | −0.0018 (5) | 0.0092 (4) | 0.0008 (4) |
O7 | 0.0340 (6) | 0.0276 (6) | 0.0546 (8) | −0.0042 (5) | 0.0233 (6) | −0.0107 (5) |
Cl1 | 0.0254 (2) | 0.02148 (19) | 0.02452 (19) | −0.00101 (13) | 0.01164 (15) | −0.00376 (12) |
C1—N1 | 1.4919 (16) | C7—H7A | 0.99 |
C1—C2 | 1.5128 (17) | C7—H7B | 0.99 |
C1—H1A | 0.99 | C8—O4 | 1.4269 (16) |
C1—H1B | 0.99 | C8—H8A | 0.99 |
C2—O1 | 1.4321 (15) | C8—H8B | 0.99 |
C2—C11 | 1.5156 (18) | C9—O4 | 1.4239 (16) |
C2—H2 | 1 | C9—C10 | 1.4939 (19) |
C3—O1 | 1.4369 (15) | C9—H9A | 0.99 |
C3—C4 | 1.503 (2) | C9—H9B | 0.99 |
C3—H3A | 0.99 | C10—O5 | 1.4326 (15) |
C3—H3B | 0.99 | C10—H10A | 0.99 |
C4—O2 | 1.4189 (17) | C10—H10B | 0.99 |
C4—H4A | 0.99 | C11—O5 | 1.4279 (15) |
C4—H4B | 0.99 | C11—H11A | 0.99 |
C5—O2 | 1.4363 (18) | C11—H11B | 0.99 |
C5—C6 | 1.503 (2) | N1—H1C | 0.91 |
C5—H5A | 0.99 | N1—H1D | 0.91 |
C5—H5B | 0.99 | N1—H1E | 0.91 |
C6—O3 | 1.4276 (16) | O6—H02 | 0.84 (2) |
C6—H6A | 0.99 | O6—H01 | 0.85 (2) |
C6—H6B | 0.99 | O7—H04 | 0.92 (2) |
C7—O3 | 1.4306 (16) | O7—H03 | 0.89 (2) |
C7—C8 | 1.497 (2) | ||
N1—C1—C2 | 111.80 (10) | C8—C7—H7B | 110.2 |
N1—C1—H1A | 109.3 | H7A—C7—H7B | 108.5 |
C2—C1—H1A | 109.3 | O4—C8—C7 | 107.34 (10) |
N1—C1—H1B | 109.3 | O4—C8—H8A | 110.2 |
C2—C1—H1B | 109.3 | C7—C8—H8A | 110.2 |
H1A—C1—H1B | 107.9 | O4—C8—H8B | 110.2 |
O1—C2—C1 | 107.74 (9) | C7—C8—H8B | 110.2 |
O1—C2—C11 | 111.72 (10) | H8A—C8—H8B | 108.5 |
C1—C2—C11 | 110.85 (11) | O4—C9—C10 | 108.15 (10) |
O1—C2—H2 | 108.8 | O4—C9—H9A | 110.1 |
C1—C2—H2 | 108.8 | C10—C9—H9A | 110.1 |
C11—C2—H2 | 108.8 | O4—C9—H9B | 110.1 |
O1—C3—C4 | 112.09 (11) | C10—C9—H9B | 110.1 |
O1—C3—H3A | 109.2 | H9A—C9—H9B | 108.4 |
C4—C3—H3A | 109.2 | O5—C10—C9 | 109.88 (10) |
O1—C3—H3B | 109.2 | O5—C10—H10A | 109.7 |
C4—C3—H3B | 109.2 | C9—C10—H10A | 109.7 |
H3A—C3—H3B | 107.9 | O5—C10—H10B | 109.7 |
O2—C4—C3 | 109.49 (11) | C9—C10—H10B | 109.7 |
O2—C4—H4A | 109.8 | H10A—C10—H10B | 108.2 |
C3—C4—H4A | 109.8 | O5—C11—C2 | 108.84 (10) |
O2—C4—H4B | 109.8 | O5—C11—H11A | 109.9 |
C3—C4—H4B | 109.8 | C2—C11—H11A | 109.9 |
H4A—C4—H4B | 108.2 | O5—C11—H11B | 109.9 |
O2—C5—C6 | 109.57 (11) | C2—C11—H11B | 109.9 |
O2—C5—H5A | 109.8 | H11A—C11—H11B | 108.3 |
C6—C5—H5A | 109.8 | C1—N1—H1C | 109.5 |
O2—C5—H5B | 109.8 | C1—N1—H1D | 109.5 |
C6—C5—H5B | 109.8 | H1C—N1—H1D | 109.5 |
H5A—C5—H5B | 108.2 | C1—N1—H1E | 109.5 |
O3—C6—C5 | 111.45 (12) | H1C—N1—H1E | 109.5 |
O3—C6—H6A | 109.3 | H1D—N1—H1E | 109.5 |
C5—C6—H6A | 109.3 | C2—O1—C3 | 113.76 (9) |
O3—C6—H6B | 109.3 | C4—O2—C5 | 113.96 (11) |
C5—C6—H6B | 109.3 | C6—O3—C7 | 114.13 (10) |
H6A—C6—H6B | 108 | C9—O4—C8 | 112.77 (10) |
O3—C7—C8 | 107.77 (11) | C11—O5—C10 | 111.80 (9) |
O3—C7—H7A | 110.2 | H02—O6—H01 | 105.9 (19) |
C8—C7—H7A | 110.2 | H04—O7—H03 | 104.2 (18) |
O3—C7—H7B | 110.2 | ||
N1—C1—C2—O1 | 50.97 (13) | C4—C3—O1—C2 | −119.12 (12) |
N1—C1—C2—C11 | 173.49 (10) | C3—C4—O2—C5 | −164.72 (11) |
O1—C3—C4—O2 | −66.88 (14) | C6—C5—O2—C4 | −132.98 (13) |
O2—C5—C6—O3 | 61.19 (16) | C5—C6—O3—C7 | 77.79 (14) |
O3—C7—C8—O4 | 66.68 (13) | C8—C7—O3—C6 | −165.35 (11) |
O4—C9—C10—O5 | −65.84 (13) | C10—C9—O4—C8 | −176.75 (10) |
O1—C2—C11—O5 | 55.69 (13) | C7—C8—O4—C9 | −170.19 (10) |
C1—C2—C11—O5 | −64.49 (13) | C2—C11—O5—C10 | −172.40 (10) |
C1—C2—O1—C3 | −163.06 (10) | C9—C10—O5—C11 | 157.03 (10) |
C11—C2—O1—C3 | 74.96 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H01···Cl1 | 0.85 (2) | 2.31 (2) | 3.1633 (12) | 178 (2) |
O6—H02···Cl1i | 0.84 (2) | 2.44 (2) | 3.2711 (12) | 174.7 (18) |
N1—H1C···O1ii | 0.91 | 2.52 | 3.1063 (14) | 122 |
N1—H1C···O5ii | 0.91 | 2.13 | 2.9783 (13) | 154 |
N1—H1D···O3ii | 0.91 | 1.91 | 2.7772 (14) | 158 |
N1—H1D···O4ii | 0.91 | 2.58 | 3.0662 (14) | 114 |
N1—H1E···Cl1 | 0.91 | 2.27 | 3.1640 (11) | 168 |
O7—H03···Cl1 | 0.89 (2) | 2.39 (2) | 3.2757 (13) | 172.9 (18) |
O7—H04···O6i | 0.92 (2) | 1.93 (2) | 2.8397 (16) | 171.6 (18) |
C1—H1B···O1ii | 0.99 | 2.40 | 3.1418 (16) | 131 |
C9—H9B···O2iii | 0.99 | 2.54 | 3.4810 (19) | 159 |
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) −x+1/2, −y+1/2, −z; (iii) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C11H24NO5+·Cl−·2H2O |
Mr | 321.79 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 120 |
a, b, c (Å) | 21.4218 (4), 7.8864 (2), 19.7794 (4) |
β (°) | 109.328 (1) |
V (Å3) | 3153.22 (12) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.27 |
Crystal size (mm) | 0.24 × 0.1 × 0.04 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan (Blessing, 1997) |
Tmin, Tmax | 0.938, 0.989 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14261, 3595, 3010 |
Rint | 0.051 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.087, 1.04 |
No. of reflections | 3595 |
No. of parameters | 199 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.27, −0.31 |
Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), DENZO and COLLECT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 1990).
C1—N1 | 1.4919 (16) | C7—O3 | 1.4306 (16) |
C2—O1 | 1.4321 (15) | C8—O4 | 1.4269 (16) |
C3—O1 | 1.4369 (15) | C9—O4 | 1.4239 (16) |
C4—O2 | 1.4189 (17) | C10—O5 | 1.4326 (15) |
C5—O2 | 1.4363 (18) | C11—O5 | 1.4279 (15) |
C6—O3 | 1.4276 (16) | ||
C2—O1—C3 | 113.76 (9) | C9—O4—C8 | 112.77 (10) |
C4—O2—C5 | 113.96 (11) | C11—O5—C10 | 111.80 (9) |
C6—O3—C7 | 114.13 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H01···Cl1 | 0.85 (2) | 2.31 (2) | 3.1633 (12) | 178 (2) |
O6—H02···Cl1i | 0.84 (2) | 2.44 (2) | 3.2711 (12) | 174.7 (18) |
N1—H1C···O1ii | 0.91 | 2.52 | 3.1063 (14) | 122 |
N1—H1C···O5ii | 0.91 | 2.13 | 2.9783 (13) | 154 |
N1—H1D···O3ii | 0.91 | 1.91 | 2.7772 (14) | 158 |
N1—H1D···O4ii | 0.91 | 2.58 | 3.0662 (14) | 114 |
N1—H1E···Cl1 | 0.91 | 2.27 | 3.1640 (11) | 168 |
O7—H03···Cl1 | 0.89 (2) | 2.39 (2) | 3.2757 (13) | 172.9 (18) |
O7—H04···O6i | 0.92 (2) | 1.93 (2) | 2.8397 (16) | 171.6 (18) |
C1—H1B···O1ii | 0.99 | 2.40 | 3.1418 (16) | 131 |
C9—H9B···O2iii | 0.99 | 2.54 | 3.4810 (19) | 159 |
Symmetry codes: (i) −x+1/2, y+1/2, −z+1/2; (ii) −x+1/2, −y+1/2, −z; (iii) x, y−1, z. |
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The title compound, (I), was the sole crystalline product from an attempted substitution reaction on hexachlorotriphosphazatriene by 2-aminomethyl-15-crown[5] and is shown to be (Fig. 1) the protonated crown ether complexed with a chloride anion and two waters of crystallization.
The bond lengths and angles conform to standard values as observed in the Cambridge Structural Database (Allen & Kennard, 1993). A search of the CSD revealed there to be no such similar monosubstituted 15-crown[5] structures.
The macrocycle adopts a conformation such that the maximum deviation from the mean ring plane is 0.928 (6) Å, with the amine (N1) situated 1.92 (3) Å above this plane. The average cross-ring O···O separation is 2.840 (5) Å, which is of a similar order of magnitudte to that of 2.793 (6) and 2.805 (5) Å of uncoordinated 15-crown[5] found in the CSD (CSD refcodes CIGSAM and DUCNEU, respectively).
Interestingly, the water molecules and chloride ion are not complexed by the crown ether, however an extensive supramolecular array is formed by means of numerous hydrogen bonds (Fig. 2). These intermolecular interactions are detailed in Table 2. The crown ethers associate solely with each other, forming dimers linked by a methylene–oxygen and two amine–oxygen interactions. These dimers are connected together, to form a three-dimensional structure, via clusters of water molecules hydrogen bonded to chloride anions. A total of three water molecules are coordinated by two chloride ions. Each chloride is involved in the formation of four hydrogen bonds (three to H2O and one to the ether). The water molecule of O6 in participates in three, and that of O7 in two, classicalhydrogenH-bonding interactions.