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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, C15H23NO2, 1, and 1-[(2,3-di­methyl­phen­oxy)eth­yl]piperidin-4-ol, C15H23NO2, 2, crystallize in the ortho­rhom­bic system (space groups P212121 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, C15H23NO3·H2O, 3, crystallizes in the monoclinic space group P21/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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619015948/fn3328sup1.cif
Contains datablocks global, 1, 2, 3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619015948/fn33281sup2.hkl
Contains datablock 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619015948/fn33282sup3.hkl
Contains datablock 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619015948/fn33283sup4.hkl
Contains datablock 3

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619015948/fn33281sup5.cml
Supplementary material

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619015948/fn33282sup6.cml
Supplementary material

CCDC references: 1968203; 1968202; 1968201

Computing details top

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
C15H23NO2F(000) = 544
Mr = 249.34Dx = 1.196 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 9663 reflections
a = 15.3994 (2) Åθ = 3.7–28.5°
b = 11.5152 (1) ŵ = 0.08 mm1
c = 7.8087 (1) ÅT = 130 K
V = 1384.69 (3) Å3Prism, colourless
Z = 40.37 × 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 tube3114 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.029
Detector resolution: 10.3756 pixels mm-1θmax = 28.6°, θmin = 3.2°
ω scansh = 2020
Absorption correction: gaussian
(CrysAlis PRO; Rigaku OD, 2015)
k = 1514
Tmin = 0.977, Tmax = 0.991l = 1010
19258 measured reflections
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH 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 = 0.84Δρmax = 0.20 e Å3
3382 reflectionsΔρmin = 0.18 e Å3
169 parametersAbsolute structure: Flack x determined using 1219 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraintsAbsolute 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
xyzUiso*/Ueq
O20.16915 (9)0.06194 (11)0.69174 (17)0.0256 (3)
C130.13329 (11)0.00996 (15)0.5421 (2)0.0222 (4)
H130.0695380.0005650.5620650.027*
C140.14435 (12)0.08523 (15)0.3827 (2)0.0234 (4)
H14A0.2068340.1008110.3637590.028*
H14B0.1147150.1605910.4003130.028*
C150.10651 (11)0.02515 (15)0.2256 (2)0.0221 (4)
H15A0.1163280.0741360.1232040.027*
H15B0.0430820.0155060.2405320.027*
N10.14705 (9)0.08964 (12)0.19924 (18)0.0183 (3)
C110.13015 (12)0.16402 (15)0.3493 (2)0.0220 (4)
H11A0.0667420.1727060.3658540.026*
H11B0.1551460.2421110.3297640.026*
C120.17050 (12)0.11024 (15)0.5088 (2)0.0225 (4)
H12A0.2341780.1045250.493580.027*
H12B0.1590510.16080.608780.027*
C100.11415 (12)0.14147 (15)0.0401 (2)0.0211 (3)
H10A0.0503370.1499610.0489780.025*
H10B0.1264080.0879070.0561020.025*
C90.15369 (11)0.25962 (15)0.0003 (2)0.0206 (3)
H9A0.210070.2682010.0592420.025*
H9B0.1638590.2668610.1250720.025*
O10.09434 (8)0.34825 (10)0.05612 (16)0.0215 (3)
C10.11230 (10)0.45919 (14)0.0056 (2)0.0183 (3)
C20.09045 (11)0.48807 (15)0.1742 (2)0.0207 (3)
C30.10356 (12)0.60290 (16)0.2258 (2)0.0261 (4)
H30.0894550.6248560.3397360.031*
C40.13665 (13)0.68538 (16)0.1146 (3)0.0292 (4)
H40.1452710.7629770.1522550.035*
C50.15720 (12)0.65409 (16)0.0525 (3)0.0261 (4)
H50.1797640.710960.1286090.031*
C60.14524 (11)0.54069 (15)0.1103 (2)0.0212 (4)
C80.05091 (12)0.40052 (17)0.2947 (2)0.0268 (4)
H8A0.0095150.4395990.3706320.04*
H8B0.0206540.3406080.2284740.04*
H8C0.0968510.3644410.3633320.04*
C70.16506 (12)0.50771 (17)0.2925 (2)0.0265 (4)
H7A0.2149030.4548290.2948120.04*
H7B0.1144470.4690690.3429160.04*
H7C0.1787360.5777480.3585090.04*
H20.228 (2)0.067 (2)0.683 (4)0.056 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0238 (6)0.0302 (7)0.0228 (6)0.0007 (5)0.0012 (5)0.0110 (5)
C130.0216 (8)0.0242 (8)0.0208 (8)0.0021 (7)0.0007 (7)0.0067 (7)
C140.0270 (9)0.0170 (8)0.0261 (9)0.0022 (7)0.0018 (7)0.0044 (7)
C150.0248 (8)0.0180 (8)0.0236 (8)0.0030 (6)0.0039 (7)0.0010 (6)
N10.0229 (7)0.0153 (6)0.0166 (6)0.0003 (5)0.0013 (6)0.0005 (5)
C110.0294 (9)0.0179 (8)0.0187 (8)0.0040 (6)0.0012 (7)0.0002 (6)
C120.0296 (9)0.0201 (8)0.0177 (8)0.0009 (7)0.0012 (7)0.0001 (6)
C100.0253 (8)0.0194 (8)0.0187 (8)0.0007 (6)0.0037 (7)0.0019 (6)
C90.0241 (8)0.0189 (8)0.0188 (7)0.0031 (6)0.0014 (7)0.0016 (6)
O10.0252 (6)0.0163 (5)0.0231 (6)0.0016 (5)0.0059 (5)0.0032 (5)
C10.0164 (7)0.0182 (7)0.0203 (8)0.0024 (6)0.0029 (6)0.0029 (6)
C20.0192 (7)0.0219 (8)0.0210 (8)0.0030 (6)0.0011 (7)0.0017 (6)
C30.0265 (8)0.0274 (9)0.0244 (9)0.0044 (7)0.0022 (8)0.0085 (7)
C40.0307 (10)0.0207 (8)0.0361 (11)0.0018 (7)0.0045 (8)0.0074 (7)
C50.0262 (9)0.0207 (8)0.0313 (10)0.0012 (7)0.0014 (8)0.0021 (7)
C60.0190 (8)0.0219 (8)0.0226 (8)0.0024 (6)0.0015 (7)0.0000 (7)
C80.0320 (9)0.0279 (9)0.0205 (8)0.0031 (7)0.0039 (8)0.0012 (7)
C70.0285 (9)0.0292 (9)0.0218 (9)0.0003 (7)0.0032 (8)0.0012 (7)
Geometric parameters (Å, º) top
O2—C131.424 (2)C9—O11.439 (2)
O2—H20.91 (3)C9—H9A0.99
C13—C121.520 (2)C9—H9B0.99
C13—C141.526 (3)O1—C11.393 (2)
C13—H131C1—C21.399 (2)
C14—C151.524 (2)C1—C61.399 (3)
C14—H14A0.99C2—C31.397 (2)
C14—H14B0.99C2—C81.508 (3)
C15—N11.476 (2)C3—C41.384 (3)
C15—H15A0.99C3—H30.95
C15—H15B0.99C4—C51.390 (3)
N1—C101.469 (2)C4—H40.95
N1—C111.474 (2)C5—C61.394 (2)
C11—C121.523 (2)C5—H50.95
C11—H11A0.99C6—C71.503 (2)
C11—H11B0.99C8—H8A0.98
C12—H12A0.99C8—H8B0.98
C12—H12B0.99C8—H8C0.98
C10—C91.524 (2)C7—H7A0.98
C10—H10A0.99C7—H7B0.98
C10—H10B0.99C7—H7C0.98
C13—O2—H2110.2 (19)H10A—C10—H10B107.7
O2—C13—C12112.15 (14)O1—C9—C10108.42 (14)
O2—C13—C14112.78 (14)O1—C9—H9A110
C12—C13—C14109.60 (14)C10—C9—H9A110
O2—C13—H13107.3O1—C9—H9B110
C12—C13—H13107.3C10—C9—H9B110
C14—C13—H13107.3H9A—C9—H9B108.4
C15—C14—C13110.86 (14)C1—O1—C9114.72 (12)
C15—C14—H14A109.5O1—C1—C2119.74 (15)
C13—C14—H14A109.5O1—C1—C6117.58 (15)
C15—C14—H14B109.5C2—C1—C6122.46 (16)
C13—C14—H14B109.5C3—C2—C1117.52 (16)
H14A—C14—H14B108.1C3—C2—C8120.73 (16)
N1—C15—C14110.91 (14)C1—C2—C8121.71 (16)
N1—C15—H15A109.5C4—C3—C2121.43 (17)
C14—C15—H15A109.5C4—C3—H3119.3
N1—C15—H15B109.5C2—C3—H3119.3
C14—C15—H15B109.5C3—C4—C5119.66 (17)
H15A—C15—H15B108C3—C4—H4120.2
C10—N1—C11112.06 (13)C5—C4—H4120.2
C10—N1—C15109.63 (13)C4—C5—C6121.12 (17)
C11—N1—C15109.56 (13)C4—C5—H5119.4
N1—C11—C12109.97 (13)C6—C5—H5119.4
N1—C11—H11A109.7C5—C6—C1117.81 (16)
C12—C11—H11A109.7C5—C6—C7121.08 (17)
N1—C11—H11B109.7C1—C6—C7121.09 (16)
C12—C11—H11B109.7C2—C8—H8A109.5
H11A—C11—H11B108.2C2—C8—H8B109.5
C13—C12—C11110.88 (15)H8A—C8—H8B109.5
C13—C12—H12A109.5C2—C8—H8C109.5
C11—C12—H12A109.5H8A—C8—H8C109.5
C13—C12—H12B109.5H8B—C8—H8C109.5
C11—C12—H12B109.5C6—C7—H7A109.5
H12A—C12—H12B108.1C6—C7—H7B109.5
N1—C10—C9113.60 (14)H7A—C7—H7B109.5
N1—C10—H10A108.8C6—C7—H7C109.5
C9—C10—H10A108.8H7A—C7—H7C109.5
N1—C10—H10B108.8H7B—C7—H7C109.5
C9—C10—H10B108.8
O2—C13—C14—C15178.98 (13)C9—O1—C1—C6108.10 (17)
C12—C13—C14—C1553.28 (19)O1—C1—C2—C3175.12 (15)
C13—C14—C15—N157.04 (19)C6—C1—C2—C30.7 (2)
C14—C15—N1—C10175.75 (14)O1—C1—C2—C82.5 (2)
C14—C15—N1—C1160.90 (18)C6—C1—C2—C8176.92 (16)
C10—N1—C11—C12176.38 (14)C1—C2—C3—C40.2 (3)
C15—N1—C11—C1261.71 (18)C8—C2—C3—C4177.46 (17)
O2—C13—C12—C11179.33 (14)C2—C3—C4—C50.2 (3)
C14—C13—C12—C1154.61 (19)C3—C4—C5—C60.1 (3)
N1—C11—C12—C1359.33 (19)C4—C5—C6—C10.3 (3)
C11—N1—C10—C959.28 (19)C4—C5—C6—C7178.22 (17)
C15—N1—C10—C9178.85 (13)O1—C1—C6—C5175.29 (15)
N1—C10—C9—O198.02 (16)C2—C1—C6—C50.8 (2)
C10—C9—O1—C1166.41 (14)O1—C1—C6—C73.3 (2)
C9—O1—C1—C277.24 (19)C2—C1—C6—C7177.77 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···N1i0.91 (3)1.94 (3)2.849 (2)170 (3)
C4—H4···O2ii0.952.383.317 (2)167
C10—H10B···O2iii0.992.703.688 (2)176
C11—H11B···O10.992.633.169 (2)114
Symmetry codes: (i) x+1/2, y, z+1/2; (ii) x, y+1, z1; (iii) x, y, z1.
1-[(2,3-Dimethylphenoxy)ethyl]piperidin-4-ol (2) top
Crystal data top
C15H23NO2F(000) = 1088
Mr = 249.34Dx = 1.201 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 3538 reflections
a = 8.5170 (2) Åθ = 1.0–27.5°
b = 10.0190 (2) ŵ = 0.08 mm1
c = 32.3230 (7) ÅT = 293 K
V = 2758.18 (10) Å3Block, colourless
Z = 80.32 × 0.17 × 0.07 mm
Data collection top
Nonius KappaCCD
diffractometer
3144 independent reflections
Horizonally mounted graphite crystal monochromator2396 reflections with I > 2σ(I)
Detector resolution: 9 pixels mm-1Rint = 0.032
CCD scansθmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan
(DENZO-SMN; Otwinowski & Minor, 1997)
h = 1111
Tmin = 0.930, Tmax = 1k = 1212
5773 measured reflectionsl = 4141
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH 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 = 1.05Δρmax = 0.23 e Å3
3144 reflectionsΔρmin = 0.20 e Å3
170 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction 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
xyzUiso*/Ueq
O20.26513 (12)0.08844 (9)0.74773 (3)0.0200 (2)
O10.33186 (11)0.15251 (9)0.61065 (3)0.0191 (2)
C130.18745 (15)0.16680 (13)0.71713 (4)0.0156 (3)
H130.26670.20690.6990.019*
C120.08487 (16)0.07355 (13)0.69151 (4)0.0158 (3)
H12A0.15130.01320.67590.019*
H12B0.02010.02030.70990.019*
N10.11833 (13)0.24700 (11)0.68489 (3)0.0138 (2)
C110.02041 (16)0.15077 (13)0.66176 (4)0.0157 (3)
H11A0.08740.08910.64680.019*
H11B0.04380.19810.64180.019*
C140.09049 (16)0.27767 (13)0.73647 (4)0.0160 (3)
H14A0.16030.34310.74870.019*
H14B0.02580.24070.75830.019*
C100.23079 (16)0.31749 (13)0.65819 (4)0.0174 (3)
H10A0.26730.39620.67280.021*
H10B0.17570.34760.63360.021*
C30.51287 (19)0.10298 (14)0.54634 (4)0.0231 (3)
C90.37268 (16)0.23744 (14)0.64466 (4)0.0181 (3)
H9A0.45630.29750.63640.022*
H9B0.41020.18370.66760.022*
C10.44963 (17)0.07585 (14)0.59346 (4)0.0179 (3)
C70.22865 (18)0.03547 (15)0.55377 (4)0.0234 (3)
H7A0.16780.02680.56970.035*
H7B0.19530.12470.560.035*
H7C0.21370.01830.52480.035*
C150.01396 (16)0.34595 (13)0.70482 (4)0.0159 (3)
H15A0.05050.3890.6840.019*
H15B0.07670.4140.71830.019*
C60.60738 (17)0.09027 (15)0.60366 (4)0.0226 (3)
H60.63880.15470.62270.027*
C40.67097 (19)0.08875 (16)0.55700 (4)0.0272 (4)
H40.74560.14440.54510.033*
C20.39999 (17)0.02015 (14)0.56446 (4)0.0188 (3)
C50.71736 (18)0.00727 (16)0.58512 (4)0.0267 (4)
H50.82310.01640.59170.032*
C80.4642 (2)0.20808 (16)0.51551 (5)0.0316 (4)
H8A0.55370.26130.50810.047*
H8B0.42280.16580.49120.047*
H8C0.38510.26420.52760.047*
H20.297 (2)0.1413 (18)0.7677 (6)0.040 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0214 (5)0.0151 (5)0.0235 (5)0.0017 (4)0.0078 (4)0.0013 (4)
O10.0185 (5)0.0225 (5)0.0163 (5)0.0001 (4)0.0012 (4)0.0054 (4)
C130.0135 (6)0.0157 (6)0.0175 (6)0.0003 (5)0.0020 (5)0.0009 (5)
C120.0154 (7)0.0148 (7)0.0171 (6)0.0016 (6)0.0003 (5)0.0026 (5)
N10.0155 (5)0.0124 (5)0.0135 (5)0.0008 (5)0.0015 (5)0.0004 (4)
C110.0171 (7)0.0158 (7)0.0140 (6)0.0007 (6)0.0012 (5)0.0026 (5)
C140.0174 (6)0.0139 (6)0.0168 (6)0.0012 (6)0.0025 (5)0.0018 (5)
C100.0199 (7)0.0160 (7)0.0164 (6)0.0022 (6)0.0024 (6)0.0011 (5)
C30.0354 (9)0.0181 (7)0.0157 (6)0.0005 (7)0.0040 (6)0.0013 (6)
C90.0187 (7)0.0206 (7)0.0151 (6)0.0036 (6)0.0020 (6)0.0028 (5)
C10.0214 (7)0.0186 (7)0.0136 (6)0.0007 (6)0.0040 (6)0.0007 (5)
C70.0303 (8)0.0232 (7)0.0166 (6)0.0043 (7)0.0014 (6)0.0010 (6)
C150.0178 (7)0.0119 (6)0.0179 (6)0.0012 (5)0.0007 (5)0.0009 (5)
C60.0233 (7)0.0273 (8)0.0173 (6)0.0012 (7)0.0012 (6)0.0033 (6)
C40.0316 (8)0.0297 (8)0.0203 (7)0.0088 (7)0.0068 (7)0.0012 (6)
C20.0252 (8)0.0180 (7)0.0132 (6)0.0030 (6)0.0022 (6)0.0029 (5)
C50.0211 (8)0.0372 (9)0.0219 (7)0.0037 (7)0.0019 (6)0.0027 (7)
C80.0468 (10)0.0238 (8)0.0242 (7)0.0008 (8)0.0049 (8)0.0054 (6)
Geometric parameters (Å, º) top
O2—C131.4257 (16)C3—C41.397 (2)
O2—H20.876 (19)C3—C21.399 (2)
O1—C11.3802 (16)C3—C81.508 (2)
O1—C91.4330 (15)C9—H9A0.97
C13—C141.5188 (18)C9—H9B0.97
C13—C121.5236 (18)C1—C61.391 (2)
C13—H130.98C1—C21.4078 (19)
C12—C111.5256 (18)C7—C21.507 (2)
C12—H12A0.97C7—H7A0.96
C12—H12B0.97C7—H7B0.96
N1—C101.4702 (17)C7—H7C0.96
N1—C111.4778 (16)C15—H15A0.97
N1—C151.4791 (16)C15—H15B0.97
C11—H11A0.97C6—C51.389 (2)
C11—H11B0.97C6—H60.93
C14—C151.5185 (18)C4—C51.381 (2)
C14—H14A0.97C4—H40.93
C14—H14B0.97C5—H50.93
C10—C91.5148 (19)C8—H8A0.96
C10—H10A0.97C8—H8B0.96
C10—H10B0.97C8—H8C0.96
C13—O2—H2108.6 (12)O1—C9—H9A109.7
C1—O1—C9117.59 (10)C10—C9—H9A109.7
O2—C13—C14111.68 (11)O1—C9—H9B109.7
O2—C13—C12107.78 (10)C10—C9—H9B109.7
C14—C13—C12111.12 (11)H9A—C9—H9B108.2
O2—C13—H13108.7O1—C1—C6123.28 (12)
C14—C13—H13108.7O1—C1—C2115.47 (12)
C12—C13—H13108.7C6—C1—C2121.26 (13)
C13—C12—C11111.63 (11)C2—C7—H7A109.5
C13—C12—H12A109.3C2—C7—H7B109.5
C11—C12—H12A109.3H7A—C7—H7B109.5
C13—C12—H12B109.3C2—C7—H7C109.5
C11—C12—H12B109.3H7A—C7—H7C109.5
H12A—C12—H12B108H7B—C7—H7C109.5
C10—N1—C11112.58 (10)N1—C15—C14110.09 (10)
C10—N1—C15108.98 (10)N1—C15—H15A109.6
C11—N1—C15108.57 (10)C14—C15—H15A109.6
N1—C11—C12110.10 (10)N1—C15—H15B109.6
N1—C11—H11A109.6C14—C15—H15B109.6
C12—C11—H11A109.6H15A—C15—H15B108.2
N1—C11—H11B109.6C5—C6—C1119.15 (14)
C12—C11—H11B109.6C5—C6—H6120.4
H11A—C11—H11B108.2C1—C6—H6120.4
C15—C14—C13111.76 (11)C5—C4—C3120.60 (14)
C15—C14—H14A109.3C5—C4—H4119.7
C13—C14—H14A109.3C3—C4—H4119.7
C15—C14—H14B109.3C3—C2—C1118.54 (13)
C13—C14—H14B109.3C3—C2—C7120.59 (13)
H14A—C14—H14B107.9C1—C2—C7120.86 (13)
N1—C10—C9115.78 (11)C4—C5—C6120.55 (14)
N1—C10—H10A108.3C4—C5—H5119.7
C9—C10—H10A108.3C6—C5—H5119.7
N1—C10—H10B108.3C3—C8—H8A109.5
C9—C10—H10B108.3C3—C8—H8B109.5
H10A—C10—H10B107.4H8A—C8—H8B109.5
C4—C3—C2119.91 (13)C3—C8—H8C109.5
C4—C3—C8119.95 (14)H8A—C8—H8C109.5
C2—C3—C8120.14 (14)H8B—C8—H8C109.5
O1—C9—C10110.02 (11)
O2—C13—C12—C11172.12 (10)C13—C14—C15—N157.39 (14)
C14—C13—C12—C1149.44 (15)O1—C1—C6—C5179.16 (13)
C10—N1—C11—C12175.75 (11)C2—C1—C6—C50.6 (2)
C15—N1—C11—C1263.50 (13)C2—C3—C4—C50.5 (2)
C13—C12—C11—N156.80 (14)C8—C3—C4—C5179.86 (14)
O2—C13—C14—C15170.18 (11)C4—C3—C2—C10.3 (2)
C12—C13—C14—C1549.79 (15)C8—C3—C2—C1179.30 (13)
C11—N1—C10—C975.50 (14)C4—C3—C2—C7179.12 (13)
C15—N1—C10—C9163.99 (11)C8—C3—C2—C70.5 (2)
C1—O1—C9—C10177.69 (11)O1—C1—C2—C3178.90 (11)
N1—C10—C9—O180.35 (14)C6—C1—C2—C30.9 (2)
C9—O1—C1—C68.93 (19)O1—C1—C2—C70.13 (18)
C9—O1—C1—C2170.88 (11)C6—C1—C2—C7179.69 (13)
C10—N1—C15—C14173.25 (10)C3—C4—C5—C60.8 (2)
C11—N1—C15—C1463.80 (13)C1—C6—C5—C40.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···N1i0.88 (2)2.00 (2)2.873 (2)174 (2)
C11—H11A···O10.972.473.125 (2)125
C12—H12B···O2ii0.972.663.361 (2)130
C14—H14A···O2iii0.972.543.367 (2)143
C15—H15B···O2iv0.972.613.582 (2)176
Symmetry codes: (i) x1/2, y, z+3/2; (ii) x+1/2, y, z+3/2; (iii) x1/2, 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·H2OF(000) = 616
Mr = 283.36Dx = 1.265 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8948 reflections
a = 19.3892 (3) Åθ = 3.4–28.5°
b = 6.1746 (1) ŵ = 0.09 mm1
c = 12.6588 (2) ÅT = 130 K
β = 100.870 (1)°Plate, colourless
V = 1488.33 (4) Å30.7 × 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 tube3043 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.027
Detector resolution: 10.3756 pixels mm-1θmax = 28.7°, θmin = 3.2°
ω scansh = 2625
Absorption correction: gaussian
(CrysAlis PRO; Rigaku OD, 2015)
k = 88
Tmin = 0.958, Tmax = 0.996l = 1616
19278 measured reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.041H 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 reflectionsΔρmax = 0.30 e Å3
195 parametersΔρmin = 0.22 e Å3
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
xyzUiso*/Ueq
C60.18360 (7)0.4839 (2)0.88111 (10)0.0218 (3)
H60.21720.4060.93130.026*
C50.15496 (7)0.6771 (2)0.91005 (11)0.0246 (3)
H50.16870.73090.98120.03*
C40.10674 (7)0.7914 (2)0.83621 (11)0.0241 (3)
H40.08810.92340.85720.029*
C30.08509 (6)0.7156 (2)0.73129 (10)0.0201 (3)
C20.11218 (6)0.5198 (2)0.70079 (10)0.0185 (3)
C10.16171 (6)0.4080 (2)0.77660 (10)0.0185 (2)
C80.03263 (7)0.8451 (2)0.65283 (12)0.0274 (3)
H8A0.02150.97960.68720.041*
H8B0.01040.76010.6310.041*
H8C0.05270.87980.58930.041*
C70.09006 (7)0.4254 (2)0.58993 (11)0.0248 (3)
H7A0.05520.31130.59170.037*
H7B0.13110.3640.5660.037*
H7C0.06950.53950.53990.037*
O10.18655 (5)0.22024 (15)0.73901 (7)0.0221 (2)
C90.24703 (6)0.1254 (2)0.80420 (10)0.0186 (2)
H9A0.23640.07540.87370.022*
H9B0.28620.23060.81850.022*
C100.26536 (6)0.0645 (2)0.73846 (10)0.0180 (2)
H10A0.2360.19050.74960.022*
H10B0.25440.02620.66120.022*
N10.34159 (5)0.12621 (16)0.76855 (8)0.0149 (2)
C150.35299 (6)0.32372 (19)0.70329 (9)0.0172 (2)
H15A0.34120.28810.62570.021*
H15B0.32130.44140.71760.021*
C140.42859 (6)0.4011 (2)0.73098 (10)0.0178 (2)
H14A0.45970.28920.70930.021*
H14B0.43370.53450.68970.021*
C130.45165 (6)0.44776 (19)0.85088 (10)0.0177 (2)
H130.50320.47870.86660.021*
C120.43674 (6)0.2520 (2)0.91632 (10)0.0180 (2)
H12A0.44790.28850.99380.022*
H12B0.46750.13060.90360.022*
C110.36056 (6)0.18069 (19)0.88695 (9)0.0161 (2)
H11A0.32970.29820.9040.019*
H11B0.35310.0520.93010.019*
O3N0.38382 (4)0.04331 (13)0.74402 (7)0.01806 (19)
O20.41483 (5)0.62803 (15)0.88469 (7)0.0219 (2)
O4W0.33503 (6)0.28560 (19)1.04411 (8)0.0306 (2)
H20.4082 (10)0.739 (3)0.8337 (16)0.049 (5)*
HWA0.3640 (11)0.325 (4)1.0031 (17)0.054 (6)*
HWB0.3526 (10)0.341 (3)1.1079 (17)0.049 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C60.0201 (6)0.0229 (6)0.0220 (6)0.0032 (5)0.0028 (5)0.0016 (5)
C50.0253 (6)0.0266 (7)0.0226 (6)0.0024 (5)0.0060 (5)0.0033 (5)
C40.0236 (6)0.0210 (6)0.0296 (7)0.0041 (5)0.0099 (5)0.0009 (5)
C30.0158 (6)0.0192 (6)0.0264 (6)0.0011 (5)0.0068 (5)0.0035 (5)
C20.0148 (5)0.0186 (6)0.0224 (6)0.0004 (4)0.0042 (5)0.0023 (5)
C10.0155 (5)0.0170 (6)0.0234 (6)0.0005 (4)0.0050 (5)0.0006 (5)
C80.0249 (7)0.0240 (7)0.0332 (7)0.0083 (5)0.0050 (5)0.0050 (6)
C70.0262 (6)0.0228 (6)0.0230 (6)0.0034 (5)0.0017 (5)0.0012 (5)
O10.0204 (4)0.0194 (4)0.0237 (5)0.0067 (3)0.0029 (4)0.0023 (4)
C90.0159 (6)0.0184 (6)0.0202 (6)0.0030 (4)0.0001 (4)0.0005 (5)
C100.0142 (5)0.0190 (6)0.0195 (6)0.0020 (4)0.0004 (4)0.0005 (5)
N10.0153 (5)0.0140 (5)0.0153 (5)0.0002 (4)0.0026 (4)0.0004 (4)
C150.0204 (6)0.0155 (5)0.0154 (5)0.0006 (4)0.0024 (4)0.0025 (4)
C140.0187 (6)0.0171 (6)0.0188 (6)0.0012 (4)0.0064 (5)0.0005 (5)
C130.0162 (5)0.0168 (6)0.0201 (6)0.0015 (4)0.0030 (4)0.0006 (5)
C120.0185 (6)0.0174 (6)0.0165 (5)0.0012 (4)0.0004 (4)0.0001 (5)
C110.0194 (6)0.0163 (5)0.0127 (5)0.0011 (4)0.0031 (4)0.0004 (4)
O3N0.0202 (4)0.0150 (4)0.0192 (4)0.0034 (3)0.0044 (3)0.0026 (3)
O20.0295 (5)0.0161 (4)0.0211 (4)0.0017 (4)0.0069 (4)0.0001 (4)
O4W0.0315 (5)0.0406 (6)0.0194 (5)0.0057 (5)0.0040 (4)0.0066 (4)
Geometric parameters (Å, º) top
C6—C11.3920 (18)C10—H10A0.99
C6—C51.3937 (18)C10—H10B0.99
C6—H60.95N1—O3N1.3994 (12)
C5—C41.3844 (19)N1—C111.5122 (14)
C5—H50.95N1—C151.5125 (15)
C4—C31.3960 (19)C15—C141.5186 (16)
C4—H40.95C15—H15A0.99
C3—C21.4010 (17)C15—H15B0.99
C3—C81.5101 (18)C14—C131.5266 (16)
C2—C11.4043 (17)C14—H14A0.99
C2—C71.5053 (17)C14—H14B0.99
C1—O11.3746 (15)C13—O21.4307 (15)
C8—H8A0.98C13—C121.5237 (16)
C8—H8B0.98C13—H131
C8—H8C0.98C12—C111.5188 (16)
C7—H7A0.98C12—H12A0.99
C7—H7B0.98C12—H12B0.99
C7—H7C0.98C11—H11A0.99
O1—C91.4262 (14)C11—H11B0.99
C9—C101.5183 (17)O2—H20.93 (2)
C9—H9A0.99O4W—HWA0.87 (2)
C9—H9B0.99O4W—HWB0.88 (2)
C10—N11.5043 (14)
C1—C6—C5118.20 (12)C9—C10—H10B109.2
C1—C6—H6120.9H10A—C10—H10B107.9
C5—C6—H6120.9O3N—N1—C10110.02 (9)
C4—C5—C6120.71 (12)O3N—N1—C11110.08 (8)
C4—C5—H5119.6C10—N1—C11110.55 (9)
C6—C5—H5119.6O3N—N1—C15109.27 (8)
C5—C4—C3121.00 (12)C10—N1—C15107.69 (9)
C5—C4—H4119.5C11—N1—C15109.19 (9)
C3—C4—H4119.5N1—C15—C14111.22 (9)
C4—C3—C2119.37 (12)N1—C15—H15A109.4
C4—C3—C8119.50 (12)C14—C15—H15A109.4
C2—C3—C8121.12 (12)N1—C15—H15B109.4
C3—C2—C1118.63 (11)C14—C15—H15B109.4
C3—C2—C7122.37 (11)H15A—C15—H15B108
C1—C2—C7119.00 (11)C15—C14—C13112.20 (10)
O1—C1—C6123.29 (11)C15—C14—H14A109.2
O1—C1—C2114.64 (11)C13—C14—H14A109.2
C6—C1—C2122.07 (12)C15—C14—H14B109.2
C3—C8—H8A109.5C13—C14—H14B109.2
C3—C8—H8B109.5H14A—C14—H14B107.9
H8A—C8—H8B109.5O2—C13—C12107.35 (10)
C3—C8—H8C109.5O2—C13—C14112.02 (10)
H8A—C8—H8C109.5C12—C13—C14109.93 (10)
H8B—C8—H8C109.5O2—C13—H13109.2
C2—C7—H7A109.5C12—C13—H13109.2
C2—C7—H7B109.5C14—C13—H13109.2
H7A—C7—H7B109.5C11—C12—C13111.86 (10)
C2—C7—H7C109.5C11—C12—H12A109.2
H7A—C7—H7C109.5C13—C12—H12A109.2
H7B—C7—H7C109.5C11—C12—H12B109.2
C1—O1—C9116.71 (9)C13—C12—H12B109.2
O1—C9—C10104.58 (9)H12A—C12—H12B107.9
O1—C9—H9A110.8N1—C11—C12110.52 (9)
C10—C9—H9A110.8N1—C11—H11A109.5
O1—C9—H9B110.8C12—C11—H11A109.5
C10—C9—H9B110.8N1—C11—H11B109.5
H9A—C9—H9B108.9C12—C11—H11B109.5
N1—C10—C9112.16 (9)H11A—C11—H11B108.1
N1—C10—H10A109.2C13—O2—H2112.1 (12)
C9—C10—H10A109.2HWA—O4W—HWB104.7 (18)
N1—C10—H10B109.2
C1—C6—C5—C40.8 (2)O1—C9—C10—N1155.73 (9)
C6—C5—C4—C30.6 (2)C9—C10—N1—O3N64.26 (12)
C5—C4—C3—C20.58 (19)C9—C10—N1—C1157.53 (13)
C5—C4—C3—C8179.75 (12)C9—C10—N1—C15176.74 (10)
C4—C3—C2—C11.40 (17)O3N—N1—C15—C1462.06 (12)
C8—C3—C2—C1178.94 (11)C10—N1—C15—C14178.46 (9)
C4—C3—C2—C7178.58 (12)C11—N1—C15—C1458.39 (12)
C8—C3—C2—C71.08 (18)N1—C15—C14—C1356.03 (13)
C5—C6—C1—O1179.72 (11)C15—C14—C13—O266.52 (13)
C5—C6—C1—C20.04 (19)C15—C14—C13—C1252.74 (13)
C3—C2—C1—O1178.63 (10)O2—C13—C12—C1168.17 (12)
C7—C2—C1—O11.39 (16)C14—C13—C12—C1153.91 (13)
C3—C2—C1—C61.15 (18)O3N—N1—C11—C1260.59 (12)
C7—C2—C1—C6178.84 (12)C10—N1—C11—C12177.66 (9)
C6—C1—O1—C912.65 (17)C15—N1—C11—C1259.36 (12)
C2—C1—O1—C9167.13 (10)C13—C12—C11—N158.26 (13)
C1—O1—C9—C10175.28 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O3Ni0.93 (2)1.76 (2)2.692 (1)171 (2)
O4W—HWA···O2ii0.87 (2)1.96 (2)2.816 (1)166 (2)
O4W—HWB···O3Niii0.88 (2)1.86 (2)2.7407 (13)176 (2)
C6—H6···O4W0.952.573.477 (2)161
C9—H9B···O2ii0.992.633.562 (2)158
C11—H11B···O4W0.992.63.587 (2)179
Symmetry codes: (i) x, y1, 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
123
C2—C1—O1—C977.24 (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
123
C2—C1—O1—C977.2 (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)

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