Aminoalkanol derivatives have attracted much interest in the field of medicinal chemistry as part of the search for new anticonvulsant drugs. In order to study the influence of the methyl substituent and
N-oxide formation on the geometry of molecules and intermolecular interactions in their crystals, three new examples have been prepared and their crystal structures determined by X-ray diffraction. 1-[(2,6-Dimethylphenoxy)ethyl]piperidin-4-ol, C
15H
23NO
2,
1, and 1-[(2,3-dimethylphenoxy)ethyl]piperidin-4-ol, C
15H
23NO
2,
2, crystallize in the orthorhombic system (space groups
P2
12
12
1 and
Pbca, respectively), with one molecule in the asymmetric unit, whereas the
N-oxide 1-[(2,3-dimethylphenoxy)ethyl]piperidin-4-ol
N-oxide monohydrate, C
15H
23NO
3·H
2O,
3, crystallizes in the monoclinic space group
P2
1/
c, with one
N-oxide molecule and one water molecule in the asymmetric unit. The geometries of the investigated compounds differ significantly with respect to the conformation of the O—C—C linker, the location of the hydroxy group in the piperidine ring and the nature of the intermolecular interactions, which were investigated by Hirshfeld surface and corresponding fingerprint analyses. The crystal packing of
1 and
2 is dominated by a network of O—H
N hydrogen bonds, while in
3, it is dominated by O—H
O hydrogen bonds and results in the formation of chains.
Supporting information
CCDC references: 1968203; 1968202; 1968201
Data collection: CrysAlis PRO (Rigaku OD, 2015) for (1), (3); COLLECT (Nonius, 1998) for (2). Cell refinement: CrysAlis PRO (Rigaku OD, 2015) for (1), (3); DENZO-SMN (Otwinowski & Minor, 1997) for (2). Data reduction: CrysAlis PRO (Rigaku OD, 2015) for (1), (3); DENZO-SMN (Otwinowski & Minor, 1997) for (2). For all structures, program(s) used to solve structure: SHELXL97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).
1-[(2,6-Dimethylphenoxy)ethyl]piperidin-4-ol (1)
top
Crystal data top
C15H23NO2 | F(000) = 544 |
Mr = 249.34 | Dx = 1.196 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 9663 reflections |
a = 15.3994 (2) Å | θ = 3.7–28.5° |
b = 11.5152 (1) Å | µ = 0.08 mm−1 |
c = 7.8087 (1) Å | T = 130 K |
V = 1384.69 (3) Å3 | Prism, colourless |
Z = 4 | 0.37 × 0.24 × 0.15 mm |
Data collection top
Rigaku OD SuperNova Dual source diffractometer with an Atlas detector | 3382 independent reflections |
Radiation source: micro-focus sealed X-ray tube | 3114 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.029 |
Detector resolution: 10.3756 pixels mm-1 | θmax = 28.6°, θmin = 3.2° |
ω scans | h = −20→20 |
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2015) | k = −15→14 |
Tmin = 0.977, Tmax = 0.991 | l = −10→10 |
19258 measured reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.035 | w = 1/[σ2(Fo2) + (0.0675P)2 + 0.4267P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.097 | (Δ/σ)max = 0.032 |
S = 0.84 | Δρmax = 0.20 e Å−3 |
3382 reflections | Δρmin = −0.18 e Å−3 |
169 parameters | Absolute structure: Flack x determined using 1219 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
0 restraints | Absolute structure parameter: −0.1 (3) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O2 | 0.16915 (9) | −0.06194 (11) | 0.69174 (17) | 0.0256 (3) | |
C13 | 0.13329 (11) | −0.00996 (15) | 0.5421 (2) | 0.0222 (4) | |
H13 | 0.069538 | −0.000565 | 0.562065 | 0.027* | |
C14 | 0.14435 (12) | −0.08523 (15) | 0.3827 (2) | 0.0234 (4) | |
H14A | 0.206834 | −0.100811 | 0.363759 | 0.028* | |
H14B | 0.114715 | −0.160591 | 0.400313 | 0.028* | |
C15 | 0.10651 (11) | −0.02515 (15) | 0.2256 (2) | 0.0221 (4) | |
H15A | 0.116328 | −0.074136 | 0.123204 | 0.027* | |
H15B | 0.043082 | −0.015506 | 0.240532 | 0.027* | |
N1 | 0.14705 (9) | 0.08964 (12) | 0.19924 (18) | 0.0183 (3) | |
C11 | 0.13015 (12) | 0.16402 (15) | 0.3493 (2) | 0.0220 (4) | |
H11A | 0.066742 | 0.172706 | 0.365854 | 0.026* | |
H11B | 0.155146 | 0.242111 | 0.329764 | 0.026* | |
C12 | 0.17050 (12) | 0.11024 (15) | 0.5088 (2) | 0.0225 (4) | |
H12A | 0.234178 | 0.104525 | 0.49358 | 0.027* | |
H12B | 0.159051 | 0.1608 | 0.60878 | 0.027* | |
C10 | 0.11415 (12) | 0.14147 (15) | 0.0401 (2) | 0.0211 (3) | |
H10A | 0.050337 | 0.149961 | 0.048978 | 0.025* | |
H10B | 0.126408 | 0.087907 | −0.056102 | 0.025* | |
C9 | 0.15369 (11) | 0.25962 (15) | −0.0003 (2) | 0.0206 (3) | |
H9A | 0.21007 | 0.268201 | 0.059242 | 0.025* | |
H9B | 0.163859 | 0.266861 | −0.125072 | 0.025* | |
O1 | 0.09434 (8) | 0.34825 (10) | 0.05612 (16) | 0.0215 (3) | |
C1 | 0.11230 (10) | 0.45919 (14) | −0.0056 (2) | 0.0183 (3) | |
C2 | 0.09045 (11) | 0.48807 (15) | −0.1742 (2) | 0.0207 (3) | |
C3 | 0.10356 (12) | 0.60290 (16) | −0.2258 (2) | 0.0261 (4) | |
H3 | 0.089455 | 0.624856 | −0.339736 | 0.031* | |
C4 | 0.13665 (13) | 0.68538 (16) | −0.1146 (3) | 0.0292 (4) | |
H4 | 0.145271 | 0.762977 | −0.152255 | 0.035* | |
C5 | 0.15720 (12) | 0.65409 (16) | 0.0525 (3) | 0.0261 (4) | |
H5 | 0.179764 | 0.71096 | 0.128609 | 0.031* | |
C6 | 0.14524 (11) | 0.54069 (15) | 0.1103 (2) | 0.0212 (4) | |
C8 | 0.05091 (12) | 0.40052 (17) | −0.2947 (2) | 0.0268 (4) | |
H8A | 0.009515 | 0.439599 | −0.370632 | 0.04* | |
H8B | 0.020654 | 0.340608 | −0.228474 | 0.04* | |
H8C | 0.096851 | 0.364441 | −0.363332 | 0.04* | |
C7 | 0.16506 (12) | 0.50771 (17) | 0.2925 (2) | 0.0265 (4) | |
H7A | 0.214903 | 0.454829 | 0.294812 | 0.04* | |
H7B | 0.114447 | 0.469069 | 0.342916 | 0.04* | |
H7C | 0.178736 | 0.577748 | 0.358509 | 0.04* | |
H2 | 0.228 (2) | −0.067 (2) | 0.683 (4) | 0.056 (9)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O2 | 0.0238 (6) | 0.0302 (7) | 0.0228 (6) | 0.0007 (5) | 0.0012 (5) | 0.0110 (5) |
C13 | 0.0216 (8) | 0.0242 (8) | 0.0208 (8) | 0.0021 (7) | 0.0007 (7) | 0.0067 (7) |
C14 | 0.0270 (9) | 0.0170 (8) | 0.0261 (9) | −0.0022 (7) | −0.0018 (7) | 0.0044 (7) |
C15 | 0.0248 (8) | 0.0180 (8) | 0.0236 (8) | −0.0030 (6) | −0.0039 (7) | 0.0010 (6) |
N1 | 0.0229 (7) | 0.0153 (6) | 0.0166 (6) | 0.0003 (5) | −0.0013 (6) | 0.0005 (5) |
C11 | 0.0294 (9) | 0.0179 (8) | 0.0187 (8) | 0.0040 (6) | 0.0012 (7) | 0.0002 (6) |
C12 | 0.0296 (9) | 0.0201 (8) | 0.0177 (8) | 0.0009 (7) | −0.0012 (7) | 0.0001 (6) |
C10 | 0.0253 (8) | 0.0194 (8) | 0.0187 (8) | 0.0007 (6) | −0.0037 (7) | 0.0019 (6) |
C9 | 0.0241 (8) | 0.0189 (8) | 0.0188 (7) | 0.0031 (6) | 0.0014 (7) | 0.0016 (6) |
O1 | 0.0252 (6) | 0.0163 (5) | 0.0231 (6) | 0.0016 (5) | 0.0059 (5) | 0.0032 (5) |
C1 | 0.0164 (7) | 0.0182 (7) | 0.0203 (8) | 0.0024 (6) | 0.0029 (6) | 0.0029 (6) |
C2 | 0.0192 (7) | 0.0219 (8) | 0.0210 (8) | 0.0030 (6) | 0.0011 (7) | 0.0017 (6) |
C3 | 0.0265 (8) | 0.0274 (9) | 0.0244 (9) | 0.0044 (7) | 0.0022 (8) | 0.0085 (7) |
C4 | 0.0307 (10) | 0.0207 (8) | 0.0361 (11) | 0.0018 (7) | 0.0045 (8) | 0.0074 (7) |
C5 | 0.0262 (9) | 0.0207 (8) | 0.0313 (10) | −0.0012 (7) | 0.0014 (8) | −0.0021 (7) |
C6 | 0.0190 (8) | 0.0219 (8) | 0.0226 (8) | 0.0024 (6) | 0.0015 (7) | 0.0000 (7) |
C8 | 0.0320 (9) | 0.0279 (9) | 0.0205 (8) | 0.0031 (7) | −0.0039 (8) | −0.0012 (7) |
C7 | 0.0285 (9) | 0.0292 (9) | 0.0218 (9) | 0.0003 (7) | −0.0032 (8) | −0.0012 (7) |
Geometric parameters (Å, º) top
O2—C13 | 1.424 (2) | C9—O1 | 1.439 (2) |
O2—H2 | 0.91 (3) | C9—H9A | 0.99 |
C13—C12 | 1.520 (2) | C9—H9B | 0.99 |
C13—C14 | 1.526 (3) | O1—C1 | 1.393 (2) |
C13—H13 | 1 | C1—C2 | 1.399 (2) |
C14—C15 | 1.524 (2) | C1—C6 | 1.399 (3) |
C14—H14A | 0.99 | C2—C3 | 1.397 (2) |
C14—H14B | 0.99 | C2—C8 | 1.508 (3) |
C15—N1 | 1.476 (2) | C3—C4 | 1.384 (3) |
C15—H15A | 0.99 | C3—H3 | 0.95 |
C15—H15B | 0.99 | C4—C5 | 1.390 (3) |
N1—C10 | 1.469 (2) | C4—H4 | 0.95 |
N1—C11 | 1.474 (2) | C5—C6 | 1.394 (2) |
C11—C12 | 1.523 (2) | C5—H5 | 0.95 |
C11—H11A | 0.99 | C6—C7 | 1.503 (2) |
C11—H11B | 0.99 | C8—H8A | 0.98 |
C12—H12A | 0.99 | C8—H8B | 0.98 |
C12—H12B | 0.99 | C8—H8C | 0.98 |
C10—C9 | 1.524 (2) | C7—H7A | 0.98 |
C10—H10A | 0.99 | C7—H7B | 0.98 |
C10—H10B | 0.99 | C7—H7C | 0.98 |
| | | |
C13—O2—H2 | 110.2 (19) | H10A—C10—H10B | 107.7 |
O2—C13—C12 | 112.15 (14) | O1—C9—C10 | 108.42 (14) |
O2—C13—C14 | 112.78 (14) | O1—C9—H9A | 110 |
C12—C13—C14 | 109.60 (14) | C10—C9—H9A | 110 |
O2—C13—H13 | 107.3 | O1—C9—H9B | 110 |
C12—C13—H13 | 107.3 | C10—C9—H9B | 110 |
C14—C13—H13 | 107.3 | H9A—C9—H9B | 108.4 |
C15—C14—C13 | 110.86 (14) | C1—O1—C9 | 114.72 (12) |
C15—C14—H14A | 109.5 | O1—C1—C2 | 119.74 (15) |
C13—C14—H14A | 109.5 | O1—C1—C6 | 117.58 (15) |
C15—C14—H14B | 109.5 | C2—C1—C6 | 122.46 (16) |
C13—C14—H14B | 109.5 | C3—C2—C1 | 117.52 (16) |
H14A—C14—H14B | 108.1 | C3—C2—C8 | 120.73 (16) |
N1—C15—C14 | 110.91 (14) | C1—C2—C8 | 121.71 (16) |
N1—C15—H15A | 109.5 | C4—C3—C2 | 121.43 (17) |
C14—C15—H15A | 109.5 | C4—C3—H3 | 119.3 |
N1—C15—H15B | 109.5 | C2—C3—H3 | 119.3 |
C14—C15—H15B | 109.5 | C3—C4—C5 | 119.66 (17) |
H15A—C15—H15B | 108 | C3—C4—H4 | 120.2 |
C10—N1—C11 | 112.06 (13) | C5—C4—H4 | 120.2 |
C10—N1—C15 | 109.63 (13) | C4—C5—C6 | 121.12 (17) |
C11—N1—C15 | 109.56 (13) | C4—C5—H5 | 119.4 |
N1—C11—C12 | 109.97 (13) | C6—C5—H5 | 119.4 |
N1—C11—H11A | 109.7 | C5—C6—C1 | 117.81 (16) |
C12—C11—H11A | 109.7 | C5—C6—C7 | 121.08 (17) |
N1—C11—H11B | 109.7 | C1—C6—C7 | 121.09 (16) |
C12—C11—H11B | 109.7 | C2—C8—H8A | 109.5 |
H11A—C11—H11B | 108.2 | C2—C8—H8B | 109.5 |
C13—C12—C11 | 110.88 (15) | H8A—C8—H8B | 109.5 |
C13—C12—H12A | 109.5 | C2—C8—H8C | 109.5 |
C11—C12—H12A | 109.5 | H8A—C8—H8C | 109.5 |
C13—C12—H12B | 109.5 | H8B—C8—H8C | 109.5 |
C11—C12—H12B | 109.5 | C6—C7—H7A | 109.5 |
H12A—C12—H12B | 108.1 | C6—C7—H7B | 109.5 |
N1—C10—C9 | 113.60 (14) | H7A—C7—H7B | 109.5 |
N1—C10—H10A | 108.8 | C6—C7—H7C | 109.5 |
C9—C10—H10A | 108.8 | H7A—C7—H7C | 109.5 |
N1—C10—H10B | 108.8 | H7B—C7—H7C | 109.5 |
C9—C10—H10B | 108.8 | | |
| | | |
O2—C13—C14—C15 | −178.98 (13) | C9—O1—C1—C6 | −108.10 (17) |
C12—C13—C14—C15 | −53.28 (19) | O1—C1—C2—C3 | 175.12 (15) |
C13—C14—C15—N1 | 57.04 (19) | C6—C1—C2—C3 | 0.7 (2) |
C14—C15—N1—C10 | 175.75 (14) | O1—C1—C2—C8 | −2.5 (2) |
C14—C15—N1—C11 | −60.90 (18) | C6—C1—C2—C8 | −176.92 (16) |
C10—N1—C11—C12 | −176.38 (14) | C1—C2—C3—C4 | −0.2 (3) |
C15—N1—C11—C12 | 61.71 (18) | C8—C2—C3—C4 | 177.46 (17) |
O2—C13—C12—C11 | −179.33 (14) | C2—C3—C4—C5 | −0.2 (3) |
C14—C13—C12—C11 | 54.61 (19) | C3—C4—C5—C6 | 0.1 (3) |
N1—C11—C12—C13 | −59.33 (19) | C4—C5—C6—C1 | 0.3 (3) |
C11—N1—C10—C9 | 59.28 (19) | C4—C5—C6—C7 | −178.22 (17) |
C15—N1—C10—C9 | −178.85 (13) | O1—C1—C6—C5 | −175.29 (15) |
N1—C10—C9—O1 | −98.02 (16) | C2—C1—C6—C5 | −0.8 (2) |
C10—C9—O1—C1 | −166.41 (14) | O1—C1—C6—C7 | 3.3 (2) |
C9—O1—C1—C2 | 77.24 (19) | C2—C1—C6—C7 | 177.77 (16) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···N1i | 0.91 (3) | 1.94 (3) | 2.849 (2) | 170 (3) |
C4—H4···O2ii | 0.95 | 2.38 | 3.317 (2) | 167 |
C10—H10B···O2iii | 0.99 | 2.70 | 3.688 (2) | 176 |
C11—H11B···O1 | 0.99 | 2.63 | 3.169 (2) | 114 |
Symmetry codes: (i) −x+1/2, −y, z+1/2; (ii) x, y+1, z−1; (iii) x, y, z−1. |
1-[(2,3-Dimethylphenoxy)ethyl]piperidin-4-ol (2)
top
Crystal data top
C15H23NO2 | F(000) = 1088 |
Mr = 249.34 | Dx = 1.201 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 3538 reflections |
a = 8.5170 (2) Å | θ = 1.0–27.5° |
b = 10.0190 (2) Å | µ = 0.08 mm−1 |
c = 32.3230 (7) Å | T = 293 K |
V = 2758.18 (10) Å3 | Block, colourless |
Z = 8 | 0.32 × 0.17 × 0.07 mm |
Data collection top
Nonius KappaCCD diffractometer | 3144 independent reflections |
Horizonally mounted graphite crystal monochromator | 2396 reflections with I > 2σ(I) |
Detector resolution: 9 pixels mm-1 | Rint = 0.032 |
CCD scans | θmax = 27.5°, θmin = 2.5° |
Absorption correction: multi-scan (DENZO-SMN; Otwinowski & Minor, 1997) | h = −11→11 |
Tmin = 0.930, Tmax = 1 | k = −12→12 |
5773 measured reflections | l = −41→41 |
Refinement top
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.043 | w = 1/[σ2(Fo2) + (0.0295P)2 + 1.3858P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.095 | (Δ/σ)max = 0.001 |
S = 1.05 | Δρmax = 0.23 e Å−3 |
3144 reflections | Δρmin = −0.20 e Å−3 |
170 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0065 (6) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O2 | −0.26513 (12) | 0.08844 (9) | 0.74773 (3) | 0.0200 (2) | |
O1 | 0.33186 (11) | 0.15251 (9) | 0.61065 (3) | 0.0191 (2) | |
C13 | −0.18745 (15) | 0.16680 (13) | 0.71713 (4) | 0.0156 (3) | |
H13 | −0.2667 | 0.2069 | 0.699 | 0.019* | |
C12 | −0.08487 (16) | 0.07355 (13) | 0.69151 (4) | 0.0158 (3) | |
H12A | −0.1513 | 0.0132 | 0.6759 | 0.019* | |
H12B | −0.0201 | 0.0203 | 0.7099 | 0.019* | |
N1 | 0.11833 (13) | 0.24700 (11) | 0.68489 (3) | 0.0138 (2) | |
C11 | 0.02041 (16) | 0.15077 (13) | 0.66176 (4) | 0.0157 (3) | |
H11A | 0.0874 | 0.0891 | 0.6468 | 0.019* | |
H11B | −0.0438 | 0.1981 | 0.6418 | 0.019* | |
C14 | −0.09049 (16) | 0.27767 (13) | 0.73647 (4) | 0.0160 (3) | |
H14A | −0.1603 | 0.3431 | 0.7487 | 0.019* | |
H14B | −0.0258 | 0.2407 | 0.7583 | 0.019* | |
C10 | 0.23079 (16) | 0.31749 (13) | 0.65819 (4) | 0.0174 (3) | |
H10A | 0.2673 | 0.3962 | 0.6728 | 0.021* | |
H10B | 0.1757 | 0.3476 | 0.6336 | 0.021* | |
C3 | 0.51287 (19) | −0.10298 (14) | 0.54634 (4) | 0.0231 (3) | |
C9 | 0.37268 (16) | 0.23744 (14) | 0.64466 (4) | 0.0181 (3) | |
H9A | 0.4563 | 0.2975 | 0.6364 | 0.022* | |
H9B | 0.4102 | 0.1837 | 0.6676 | 0.022* | |
C1 | 0.44963 (17) | 0.07585 (14) | 0.59346 (4) | 0.0179 (3) | |
C7 | 0.22865 (18) | −0.03547 (15) | 0.55377 (4) | 0.0234 (3) | |
H7A | 0.1678 | 0.0268 | 0.5697 | 0.035* | |
H7B | 0.1953 | −0.1247 | 0.56 | 0.035* | |
H7C | 0.2137 | −0.0183 | 0.5248 | 0.035* | |
C15 | 0.01396 (16) | 0.34595 (13) | 0.70482 (4) | 0.0159 (3) | |
H15A | −0.0505 | 0.389 | 0.684 | 0.019* | |
H15B | 0.0767 | 0.414 | 0.7183 | 0.019* | |
C6 | 0.60738 (17) | 0.09027 (15) | 0.60366 (4) | 0.0226 (3) | |
H6 | 0.6388 | 0.1547 | 0.6227 | 0.027* | |
C4 | 0.67097 (19) | −0.08875 (16) | 0.55700 (4) | 0.0272 (4) | |
H4 | 0.7456 | −0.1444 | 0.5451 | 0.033* | |
C2 | 0.39999 (17) | −0.02015 (14) | 0.56446 (4) | 0.0188 (3) | |
C5 | 0.71736 (18) | 0.00727 (16) | 0.58512 (4) | 0.0267 (4) | |
H5 | 0.8231 | 0.0164 | 0.5917 | 0.032* | |
C8 | 0.4642 (2) | −0.20808 (16) | 0.51551 (5) | 0.0316 (4) | |
H8A | 0.5537 | −0.2613 | 0.5081 | 0.047* | |
H8B | 0.4228 | −0.1658 | 0.4912 | 0.047* | |
H8C | 0.3851 | −0.2642 | 0.5276 | 0.047* | |
H2 | −0.297 (2) | 0.1413 (18) | 0.7677 (6) | 0.040 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O2 | 0.0214 (5) | 0.0151 (5) | 0.0235 (5) | −0.0017 (4) | 0.0078 (4) | −0.0013 (4) |
O1 | 0.0185 (5) | 0.0225 (5) | 0.0163 (5) | 0.0001 (4) | 0.0012 (4) | −0.0054 (4) |
C13 | 0.0135 (6) | 0.0157 (6) | 0.0175 (6) | 0.0003 (5) | 0.0020 (5) | 0.0009 (5) |
C12 | 0.0154 (7) | 0.0148 (7) | 0.0171 (6) | −0.0016 (6) | −0.0003 (5) | −0.0026 (5) |
N1 | 0.0155 (5) | 0.0124 (5) | 0.0135 (5) | −0.0008 (5) | 0.0015 (5) | −0.0004 (4) |
C11 | 0.0171 (7) | 0.0158 (7) | 0.0140 (6) | 0.0007 (6) | −0.0012 (5) | −0.0026 (5) |
C14 | 0.0174 (6) | 0.0139 (6) | 0.0168 (6) | 0.0012 (6) | 0.0025 (5) | −0.0018 (5) |
C10 | 0.0199 (7) | 0.0160 (7) | 0.0164 (6) | −0.0022 (6) | 0.0024 (6) | 0.0011 (5) |
C3 | 0.0354 (9) | 0.0181 (7) | 0.0157 (6) | −0.0005 (7) | 0.0040 (6) | 0.0013 (6) |
C9 | 0.0187 (7) | 0.0206 (7) | 0.0151 (6) | −0.0036 (6) | 0.0020 (6) | −0.0028 (5) |
C1 | 0.0214 (7) | 0.0186 (7) | 0.0136 (6) | 0.0007 (6) | 0.0040 (6) | 0.0007 (5) |
C7 | 0.0303 (8) | 0.0232 (7) | 0.0166 (6) | −0.0043 (7) | −0.0014 (6) | −0.0010 (6) |
C15 | 0.0178 (7) | 0.0119 (6) | 0.0179 (6) | 0.0012 (5) | 0.0007 (5) | −0.0009 (5) |
C6 | 0.0233 (7) | 0.0273 (8) | 0.0173 (6) | −0.0012 (7) | 0.0012 (6) | −0.0033 (6) |
C4 | 0.0316 (8) | 0.0297 (8) | 0.0203 (7) | 0.0088 (7) | 0.0068 (7) | −0.0012 (6) |
C2 | 0.0252 (8) | 0.0180 (7) | 0.0132 (6) | −0.0030 (6) | 0.0022 (6) | 0.0029 (5) |
C5 | 0.0211 (8) | 0.0372 (9) | 0.0219 (7) | 0.0037 (7) | 0.0019 (6) | −0.0027 (7) |
C8 | 0.0468 (10) | 0.0238 (8) | 0.0242 (7) | −0.0008 (8) | 0.0049 (8) | −0.0054 (6) |
Geometric parameters (Å, º) top
O2—C13 | 1.4257 (16) | C3—C4 | 1.397 (2) |
O2—H2 | 0.876 (19) | C3—C2 | 1.399 (2) |
O1—C1 | 1.3802 (16) | C3—C8 | 1.508 (2) |
O1—C9 | 1.4330 (15) | C9—H9A | 0.97 |
C13—C14 | 1.5188 (18) | C9—H9B | 0.97 |
C13—C12 | 1.5236 (18) | C1—C6 | 1.391 (2) |
C13—H13 | 0.98 | C1—C2 | 1.4078 (19) |
C12—C11 | 1.5256 (18) | C7—C2 | 1.507 (2) |
C12—H12A | 0.97 | C7—H7A | 0.96 |
C12—H12B | 0.97 | C7—H7B | 0.96 |
N1—C10 | 1.4702 (17) | C7—H7C | 0.96 |
N1—C11 | 1.4778 (16) | C15—H15A | 0.97 |
N1—C15 | 1.4791 (16) | C15—H15B | 0.97 |
C11—H11A | 0.97 | C6—C5 | 1.389 (2) |
C11—H11B | 0.97 | C6—H6 | 0.93 |
C14—C15 | 1.5185 (18) | C4—C5 | 1.381 (2) |
C14—H14A | 0.97 | C4—H4 | 0.93 |
C14—H14B | 0.97 | C5—H5 | 0.93 |
C10—C9 | 1.5148 (19) | C8—H8A | 0.96 |
C10—H10A | 0.97 | C8—H8B | 0.96 |
C10—H10B | 0.97 | C8—H8C | 0.96 |
| | | |
C13—O2—H2 | 108.6 (12) | O1—C9—H9A | 109.7 |
C1—O1—C9 | 117.59 (10) | C10—C9—H9A | 109.7 |
O2—C13—C14 | 111.68 (11) | O1—C9—H9B | 109.7 |
O2—C13—C12 | 107.78 (10) | C10—C9—H9B | 109.7 |
C14—C13—C12 | 111.12 (11) | H9A—C9—H9B | 108.2 |
O2—C13—H13 | 108.7 | O1—C1—C6 | 123.28 (12) |
C14—C13—H13 | 108.7 | O1—C1—C2 | 115.47 (12) |
C12—C13—H13 | 108.7 | C6—C1—C2 | 121.26 (13) |
C13—C12—C11 | 111.63 (11) | C2—C7—H7A | 109.5 |
C13—C12—H12A | 109.3 | C2—C7—H7B | 109.5 |
C11—C12—H12A | 109.3 | H7A—C7—H7B | 109.5 |
C13—C12—H12B | 109.3 | C2—C7—H7C | 109.5 |
C11—C12—H12B | 109.3 | H7A—C7—H7C | 109.5 |
H12A—C12—H12B | 108 | H7B—C7—H7C | 109.5 |
C10—N1—C11 | 112.58 (10) | N1—C15—C14 | 110.09 (10) |
C10—N1—C15 | 108.98 (10) | N1—C15—H15A | 109.6 |
C11—N1—C15 | 108.57 (10) | C14—C15—H15A | 109.6 |
N1—C11—C12 | 110.10 (10) | N1—C15—H15B | 109.6 |
N1—C11—H11A | 109.6 | C14—C15—H15B | 109.6 |
C12—C11—H11A | 109.6 | H15A—C15—H15B | 108.2 |
N1—C11—H11B | 109.6 | C5—C6—C1 | 119.15 (14) |
C12—C11—H11B | 109.6 | C5—C6—H6 | 120.4 |
H11A—C11—H11B | 108.2 | C1—C6—H6 | 120.4 |
C15—C14—C13 | 111.76 (11) | C5—C4—C3 | 120.60 (14) |
C15—C14—H14A | 109.3 | C5—C4—H4 | 119.7 |
C13—C14—H14A | 109.3 | C3—C4—H4 | 119.7 |
C15—C14—H14B | 109.3 | C3—C2—C1 | 118.54 (13) |
C13—C14—H14B | 109.3 | C3—C2—C7 | 120.59 (13) |
H14A—C14—H14B | 107.9 | C1—C2—C7 | 120.86 (13) |
N1—C10—C9 | 115.78 (11) | C4—C5—C6 | 120.55 (14) |
N1—C10—H10A | 108.3 | C4—C5—H5 | 119.7 |
C9—C10—H10A | 108.3 | C6—C5—H5 | 119.7 |
N1—C10—H10B | 108.3 | C3—C8—H8A | 109.5 |
C9—C10—H10B | 108.3 | C3—C8—H8B | 109.5 |
H10A—C10—H10B | 107.4 | H8A—C8—H8B | 109.5 |
C4—C3—C2 | 119.91 (13) | C3—C8—H8C | 109.5 |
C4—C3—C8 | 119.95 (14) | H8A—C8—H8C | 109.5 |
C2—C3—C8 | 120.14 (14) | H8B—C8—H8C | 109.5 |
O1—C9—C10 | 110.02 (11) | | |
| | | |
O2—C13—C12—C11 | −172.12 (10) | C13—C14—C15—N1 | −57.39 (14) |
C14—C13—C12—C11 | −49.44 (15) | O1—C1—C6—C5 | 179.16 (13) |
C10—N1—C11—C12 | 175.75 (11) | C2—C1—C6—C5 | −0.6 (2) |
C15—N1—C11—C12 | −63.50 (13) | C2—C3—C4—C5 | −0.5 (2) |
C13—C12—C11—N1 | 56.80 (14) | C8—C3—C4—C5 | 179.86 (14) |
O2—C13—C14—C15 | 170.18 (11) | C4—C3—C2—C1 | −0.3 (2) |
C12—C13—C14—C15 | 49.79 (15) | C8—C3—C2—C1 | 179.30 (13) |
C11—N1—C10—C9 | −75.50 (14) | C4—C3—C2—C7 | −179.12 (13) |
C15—N1—C10—C9 | 163.99 (11) | C8—C3—C2—C7 | 0.5 (2) |
C1—O1—C9—C10 | 177.69 (11) | O1—C1—C2—C3 | −178.90 (11) |
N1—C10—C9—O1 | 80.35 (14) | C6—C1—C2—C3 | 0.9 (2) |
C9—O1—C1—C6 | −8.93 (19) | O1—C1—C2—C7 | −0.13 (18) |
C9—O1—C1—C2 | 170.88 (11) | C6—C1—C2—C7 | 179.69 (13) |
C10—N1—C15—C14 | −173.25 (10) | C3—C4—C5—C6 | 0.8 (2) |
C11—N1—C15—C14 | 63.80 (13) | C1—C6—C5—C4 | −0.2 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···N1i | 0.88 (2) | 2.00 (2) | 2.873 (2) | 174 (2) |
C11—H11A···O1 | 0.97 | 2.47 | 3.125 (2) | 125 |
C12—H12B···O2ii | 0.97 | 2.66 | 3.361 (2) | 130 |
C14—H14A···O2iii | 0.97 | 2.54 | 3.367 (2) | 143 |
C15—H15B···O2iv | 0.97 | 2.61 | 3.582 (2) | 176 |
Symmetry codes: (i) x−1/2, y, −z+3/2; (ii) x+1/2, y, −z+3/2; (iii) −x−1/2, y+1/2, z; (iv) −x, y+1/2, −z+3/2. |
1-[(2,3-Dimethylphenoxy)ethyl]piperidin-4-ol
N-oxide monohydrate (3)
top
Crystal data top
C15H23NO3·H2O | F(000) = 616 |
Mr = 283.36 | Dx = 1.265 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 8948 reflections |
a = 19.3892 (3) Å | θ = 3.4–28.5° |
b = 6.1746 (1) Å | µ = 0.09 mm−1 |
c = 12.6588 (2) Å | T = 130 K |
β = 100.870 (1)° | Plate, colourless |
V = 1488.33 (4) Å3 | 0.7 × 0.23 × 0.04 mm |
Z = 4 | |
Data collection top
Rigaku OD SuperNova Dual source diffractometer with an Atlas detector | 3597 independent reflections |
Radiation source: micro-focus sealed X-ray tube | 3043 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.027 |
Detector resolution: 10.3756 pixels mm-1 | θmax = 28.7°, θmin = 3.2° |
ω scans | h = −26→25 |
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2015) | k = −8→8 |
Tmin = 0.958, Tmax = 0.996 | l = −16→16 |
19278 measured reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.041 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.104 | w = 1/[σ2(Fo2) + (0.0423P)2 + 0.7487P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
3597 reflections | Δρmax = 0.30 e Å−3 |
195 parameters | Δρmin = −0.22 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C6 | 0.18360 (7) | 0.4839 (2) | 0.88111 (10) | 0.0218 (3) | |
H6 | 0.2172 | 0.406 | 0.9313 | 0.026* | |
C5 | 0.15496 (7) | 0.6771 (2) | 0.91005 (11) | 0.0246 (3) | |
H5 | 0.1687 | 0.7309 | 0.9812 | 0.03* | |
C4 | 0.10674 (7) | 0.7914 (2) | 0.83621 (11) | 0.0241 (3) | |
H4 | 0.0881 | 0.9234 | 0.8572 | 0.029* | |
C3 | 0.08509 (6) | 0.7156 (2) | 0.73129 (10) | 0.0201 (3) | |
C2 | 0.11218 (6) | 0.5198 (2) | 0.70079 (10) | 0.0185 (3) | |
C1 | 0.16171 (6) | 0.4080 (2) | 0.77660 (10) | 0.0185 (2) | |
C8 | 0.03263 (7) | 0.8451 (2) | 0.65283 (12) | 0.0274 (3) | |
H8A | 0.0215 | 0.9796 | 0.6872 | 0.041* | |
H8B | −0.0104 | 0.7601 | 0.631 | 0.041* | |
H8C | 0.0527 | 0.8798 | 0.5893 | 0.041* | |
C7 | 0.09006 (7) | 0.4254 (2) | 0.58993 (11) | 0.0248 (3) | |
H7A | 0.0552 | 0.3113 | 0.5917 | 0.037* | |
H7B | 0.1311 | 0.364 | 0.566 | 0.037* | |
H7C | 0.0695 | 0.5395 | 0.5399 | 0.037* | |
O1 | 0.18655 (5) | 0.22024 (15) | 0.73901 (7) | 0.0221 (2) | |
C9 | 0.24703 (6) | 0.1254 (2) | 0.80420 (10) | 0.0186 (2) | |
H9A | 0.2364 | 0.0754 | 0.8737 | 0.022* | |
H9B | 0.2862 | 0.2306 | 0.8185 | 0.022* | |
C10 | 0.26536 (6) | −0.0645 (2) | 0.73846 (10) | 0.0180 (2) | |
H10A | 0.236 | −0.1905 | 0.7496 | 0.022* | |
H10B | 0.2544 | −0.0262 | 0.6612 | 0.022* | |
N1 | 0.34159 (5) | −0.12621 (16) | 0.76855 (8) | 0.0149 (2) | |
C15 | 0.35299 (6) | −0.32372 (19) | 0.70329 (9) | 0.0172 (2) | |
H15A | 0.3412 | −0.2881 | 0.6257 | 0.021* | |
H15B | 0.3213 | −0.4414 | 0.7176 | 0.021* | |
C14 | 0.42859 (6) | −0.4011 (2) | 0.73098 (10) | 0.0178 (2) | |
H14A | 0.4597 | −0.2892 | 0.7093 | 0.021* | |
H14B | 0.4337 | −0.5345 | 0.6897 | 0.021* | |
C13 | 0.45165 (6) | −0.44776 (19) | 0.85088 (10) | 0.0177 (2) | |
H13 | 0.5032 | −0.4787 | 0.8666 | 0.021* | |
C12 | 0.43674 (6) | −0.2520 (2) | 0.91632 (10) | 0.0180 (2) | |
H12A | 0.4479 | −0.2885 | 0.9938 | 0.022* | |
H12B | 0.4675 | −0.1306 | 0.9036 | 0.022* | |
C11 | 0.36056 (6) | −0.18069 (19) | 0.88695 (9) | 0.0161 (2) | |
H11A | 0.3297 | −0.2982 | 0.904 | 0.019* | |
H11B | 0.3531 | −0.052 | 0.9301 | 0.019* | |
O3N | 0.38382 (4) | 0.04331 (13) | 0.74402 (7) | 0.01806 (19) | |
O2 | 0.41483 (5) | −0.62803 (15) | 0.88469 (7) | 0.0219 (2) | |
O4W | 0.33503 (6) | 0.28560 (19) | 1.04411 (8) | 0.0306 (2) | |
H2 | 0.4082 (10) | −0.739 (3) | 0.8337 (16) | 0.049 (5)* | |
HWA | 0.3640 (11) | 0.325 (4) | 1.0031 (17) | 0.054 (6)* | |
HWB | 0.3526 (10) | 0.341 (3) | 1.1079 (17) | 0.049 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C6 | 0.0201 (6) | 0.0229 (6) | 0.0220 (6) | 0.0032 (5) | 0.0028 (5) | 0.0016 (5) |
C5 | 0.0253 (6) | 0.0266 (7) | 0.0226 (6) | 0.0024 (5) | 0.0060 (5) | −0.0033 (5) |
C4 | 0.0236 (6) | 0.0210 (6) | 0.0296 (7) | 0.0041 (5) | 0.0099 (5) | −0.0009 (5) |
C3 | 0.0158 (6) | 0.0192 (6) | 0.0264 (6) | 0.0011 (5) | 0.0068 (5) | 0.0035 (5) |
C2 | 0.0148 (5) | 0.0186 (6) | 0.0224 (6) | −0.0004 (4) | 0.0042 (5) | 0.0023 (5) |
C1 | 0.0155 (5) | 0.0170 (6) | 0.0234 (6) | 0.0005 (4) | 0.0050 (5) | 0.0006 (5) |
C8 | 0.0249 (7) | 0.0240 (7) | 0.0332 (7) | 0.0083 (5) | 0.0050 (5) | 0.0050 (6) |
C7 | 0.0262 (6) | 0.0228 (6) | 0.0230 (6) | 0.0034 (5) | −0.0017 (5) | 0.0012 (5) |
O1 | 0.0204 (4) | 0.0194 (4) | 0.0237 (5) | 0.0067 (3) | −0.0029 (4) | −0.0023 (4) |
C9 | 0.0159 (6) | 0.0184 (6) | 0.0202 (6) | 0.0030 (4) | 0.0001 (4) | 0.0005 (5) |
C10 | 0.0142 (5) | 0.0190 (6) | 0.0195 (6) | 0.0020 (4) | −0.0004 (4) | −0.0005 (5) |
N1 | 0.0153 (5) | 0.0140 (5) | 0.0153 (5) | 0.0002 (4) | 0.0026 (4) | 0.0004 (4) |
C15 | 0.0204 (6) | 0.0155 (5) | 0.0154 (5) | 0.0006 (4) | 0.0024 (4) | −0.0025 (4) |
C14 | 0.0187 (6) | 0.0171 (6) | 0.0188 (6) | 0.0012 (4) | 0.0064 (5) | −0.0005 (5) |
C13 | 0.0162 (5) | 0.0168 (6) | 0.0201 (6) | 0.0015 (4) | 0.0030 (4) | 0.0006 (5) |
C12 | 0.0185 (6) | 0.0174 (6) | 0.0165 (5) | 0.0012 (4) | −0.0004 (4) | −0.0001 (5) |
C11 | 0.0194 (6) | 0.0163 (5) | 0.0127 (5) | 0.0011 (4) | 0.0031 (4) | 0.0004 (4) |
O3N | 0.0202 (4) | 0.0150 (4) | 0.0192 (4) | −0.0034 (3) | 0.0044 (3) | 0.0026 (3) |
O2 | 0.0295 (5) | 0.0161 (4) | 0.0211 (4) | −0.0017 (4) | 0.0069 (4) | 0.0001 (4) |
O4W | 0.0315 (5) | 0.0406 (6) | 0.0194 (5) | −0.0057 (5) | 0.0040 (4) | −0.0066 (4) |
Geometric parameters (Å, º) top
C6—C1 | 1.3920 (18) | C10—H10A | 0.99 |
C6—C5 | 1.3937 (18) | C10—H10B | 0.99 |
C6—H6 | 0.95 | N1—O3N | 1.3994 (12) |
C5—C4 | 1.3844 (19) | N1—C11 | 1.5122 (14) |
C5—H5 | 0.95 | N1—C15 | 1.5125 (15) |
C4—C3 | 1.3960 (19) | C15—C14 | 1.5186 (16) |
C4—H4 | 0.95 | C15—H15A | 0.99 |
C3—C2 | 1.4010 (17) | C15—H15B | 0.99 |
C3—C8 | 1.5101 (18) | C14—C13 | 1.5266 (16) |
C2—C1 | 1.4043 (17) | C14—H14A | 0.99 |
C2—C7 | 1.5053 (17) | C14—H14B | 0.99 |
C1—O1 | 1.3746 (15) | C13—O2 | 1.4307 (15) |
C8—H8A | 0.98 | C13—C12 | 1.5237 (16) |
C8—H8B | 0.98 | C13—H13 | 1 |
C8—H8C | 0.98 | C12—C11 | 1.5188 (16) |
C7—H7A | 0.98 | C12—H12A | 0.99 |
C7—H7B | 0.98 | C12—H12B | 0.99 |
C7—H7C | 0.98 | C11—H11A | 0.99 |
O1—C9 | 1.4262 (14) | C11—H11B | 0.99 |
C9—C10 | 1.5183 (17) | O2—H2 | 0.93 (2) |
C9—H9A | 0.99 | O4W—HWA | 0.87 (2) |
C9—H9B | 0.99 | O4W—HWB | 0.88 (2) |
C10—N1 | 1.5043 (14) | | |
| | | |
C1—C6—C5 | 118.20 (12) | C9—C10—H10B | 109.2 |
C1—C6—H6 | 120.9 | H10A—C10—H10B | 107.9 |
C5—C6—H6 | 120.9 | O3N—N1—C10 | 110.02 (9) |
C4—C5—C6 | 120.71 (12) | O3N—N1—C11 | 110.08 (8) |
C4—C5—H5 | 119.6 | C10—N1—C11 | 110.55 (9) |
C6—C5—H5 | 119.6 | O3N—N1—C15 | 109.27 (8) |
C5—C4—C3 | 121.00 (12) | C10—N1—C15 | 107.69 (9) |
C5—C4—H4 | 119.5 | C11—N1—C15 | 109.19 (9) |
C3—C4—H4 | 119.5 | N1—C15—C14 | 111.22 (9) |
C4—C3—C2 | 119.37 (12) | N1—C15—H15A | 109.4 |
C4—C3—C8 | 119.50 (12) | C14—C15—H15A | 109.4 |
C2—C3—C8 | 121.12 (12) | N1—C15—H15B | 109.4 |
C3—C2—C1 | 118.63 (11) | C14—C15—H15B | 109.4 |
C3—C2—C7 | 122.37 (11) | H15A—C15—H15B | 108 |
C1—C2—C7 | 119.00 (11) | C15—C14—C13 | 112.20 (10) |
O1—C1—C6 | 123.29 (11) | C15—C14—H14A | 109.2 |
O1—C1—C2 | 114.64 (11) | C13—C14—H14A | 109.2 |
C6—C1—C2 | 122.07 (12) | C15—C14—H14B | 109.2 |
C3—C8—H8A | 109.5 | C13—C14—H14B | 109.2 |
C3—C8—H8B | 109.5 | H14A—C14—H14B | 107.9 |
H8A—C8—H8B | 109.5 | O2—C13—C12 | 107.35 (10) |
C3—C8—H8C | 109.5 | O2—C13—C14 | 112.02 (10) |
H8A—C8—H8C | 109.5 | C12—C13—C14 | 109.93 (10) |
H8B—C8—H8C | 109.5 | O2—C13—H13 | 109.2 |
C2—C7—H7A | 109.5 | C12—C13—H13 | 109.2 |
C2—C7—H7B | 109.5 | C14—C13—H13 | 109.2 |
H7A—C7—H7B | 109.5 | C11—C12—C13 | 111.86 (10) |
C2—C7—H7C | 109.5 | C11—C12—H12A | 109.2 |
H7A—C7—H7C | 109.5 | C13—C12—H12A | 109.2 |
H7B—C7—H7C | 109.5 | C11—C12—H12B | 109.2 |
C1—O1—C9 | 116.71 (9) | C13—C12—H12B | 109.2 |
O1—C9—C10 | 104.58 (9) | H12A—C12—H12B | 107.9 |
O1—C9—H9A | 110.8 | N1—C11—C12 | 110.52 (9) |
C10—C9—H9A | 110.8 | N1—C11—H11A | 109.5 |
O1—C9—H9B | 110.8 | C12—C11—H11A | 109.5 |
C10—C9—H9B | 110.8 | N1—C11—H11B | 109.5 |
H9A—C9—H9B | 108.9 | C12—C11—H11B | 109.5 |
N1—C10—C9 | 112.16 (9) | H11A—C11—H11B | 108.1 |
N1—C10—H10A | 109.2 | C13—O2—H2 | 112.1 (12) |
C9—C10—H10A | 109.2 | HWA—O4W—HWB | 104.7 (18) |
N1—C10—H10B | 109.2 | | |
| | | |
C1—C6—C5—C4 | −0.8 (2) | O1—C9—C10—N1 | 155.73 (9) |
C6—C5—C4—C3 | 0.6 (2) | C9—C10—N1—O3N | −64.26 (12) |
C5—C4—C3—C2 | 0.58 (19) | C9—C10—N1—C11 | 57.53 (13) |
C5—C4—C3—C8 | −179.75 (12) | C9—C10—N1—C15 | 176.74 (10) |
C4—C3—C2—C1 | −1.40 (17) | O3N—N1—C15—C14 | 62.06 (12) |
C8—C3—C2—C1 | 178.94 (11) | C10—N1—C15—C14 | −178.46 (9) |
C4—C3—C2—C7 | 178.58 (12) | C11—N1—C15—C14 | −58.39 (12) |
C8—C3—C2—C7 | −1.08 (18) | N1—C15—C14—C13 | 56.03 (13) |
C5—C6—C1—O1 | 179.72 (11) | C15—C14—C13—O2 | 66.52 (13) |
C5—C6—C1—C2 | −0.04 (19) | C15—C14—C13—C12 | −52.74 (13) |
C3—C2—C1—O1 | −178.63 (10) | O2—C13—C12—C11 | −68.17 (12) |
C7—C2—C1—O1 | 1.39 (16) | C14—C13—C12—C11 | 53.91 (13) |
C3—C2—C1—C6 | 1.15 (18) | O3N—N1—C11—C12 | −60.59 (12) |
C7—C2—C1—C6 | −178.84 (12) | C10—N1—C11—C12 | 177.66 (9) |
C6—C1—O1—C9 | −12.65 (17) | C15—N1—C11—C12 | 59.36 (12) |
C2—C1—O1—C9 | 167.13 (10) | C13—C12—C11—N1 | −58.26 (13) |
C1—O1—C9—C10 | −175.28 (10) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O3Ni | 0.93 (2) | 1.76 (2) | 2.692 (1) | 171 (2) |
O4W—HWA···O2ii | 0.87 (2) | 1.96 (2) | 2.816 (1) | 166 (2) |
O4W—HWB···O3Niii | 0.88 (2) | 1.86 (2) | 2.7407 (13) | 176 (2) |
C6—H6···O4W | 0.95 | 2.57 | 3.477 (2) | 161 |
C9—H9B···O2ii | 0.99 | 2.63 | 3.562 (2) | 158 |
C11—H11B···O4W | 0.99 | 2.6 | 3.587 (2) | 179 |
Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z; (iii) x, −y+1/2, z+1/2. |
Comparison of selected torsion angles (°) in 1, 2 and 3 top | 1 | 2 | 3 |
C2—C1—O1—C9 | 77.24 (19) | 170.88 (11) | 167.13 (10) |
C1—O1—C9—C10 | -166.41 (14) | 177.69 (11) | -175.28 (10) |
O1—C9—C10—N1 | -98.02 (16) | 80.35 (14) | 155.73 (9) |
C9—C10—N1—C15 | -178.85 (13) | 163.99 (11) | 176.74 (10) |
C11—C12—C13—O2 | -179.33 (14) | -172.12 (10) | -68.17 (12) |
Comparison of selected torsion angles (°) in 1, 2 and 3 top | 1 | 2 | 3 |
C2—C1—O1—C9 | 77.2 (2) | 170.9 (1) | 167.1 (1) |
C1—O1—C9—C10 | -166.4 (1) | 177.7 (1) | -175.3 (1) |
O1—C9—C10—N1 | -98.9 (2) | 80.4 (1) | 155.7 (1) |
C9—C10—N1—C15 | -178.9 (1) | -75.5 (1) | 176.7 (1) |
C11—C12—C13—O2 | -179.3 (1) | 170.2 (1) | -68.2 (1) |