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Presented herein are detailed optical, thermal, spectroscopic and structural analyses of the phase transformation occurring in tapentadol hydro­chloride (C14H24NO+·Cl), a phenomenon already reported [Fischer et al. (2006); Patent: WO 2006000441 A2]. The thermal behaviour of the compound was studied using single-crystal X-ray diffraction, differential scanning calorimetry and Raman scattering measurements. The compound undergoes a first-order reversible phase transition at Theat = 318.0 (1) K, Tcool = 300.0 (1) K, as assessed by the coexistence of both phases in the vicinity of the transition and the abrupt changes observed in the unit-cell parameters with temperature. The process is accompanied by clear thermosalient behaviour, with a conspicuous movement of the samples. On cooling, the transformation leads from a P212121 symmetry (Z′ = 1) to P21, with an abrupt change in β [90 ↔ 94.78 (1)°] and duplication of the asymmetric unit contents (Z′ = 2). The main structural differences observed across the transition are extremely small, with almost no changes in the stronger, non-covalent interaction scheme involving the `conventional' (N—H...Cl, O—H...Cl) hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520619001148/lo5043sup1.cif
Contains datablocks global, 150K, 250K, 325K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520619001148/lo5043150Ksup2.hkl
Contains datablock 150K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520619001148/lo5043250Ksup3.hkl
Contains datablock 250K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520619001148/lo5043325Ksup4.hkl
Contains datablock 325K

mp4

Moving Picture Experts Group (MP4) video file https://doi.org/10.1107/S2052520619001148/lo5043sup5.mp4
Video S1

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052520619001148/lo5043sup6.pdf
Supporting tables and figures

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2052520619001148/lo5043150Ksup7.cml
Supplementary material

CCDC references: 1892585; 1892586; 1892587

Computing details top

For all structures, data collection: Bruker APEX2; cell refinement: Bruker SAINT; data reduction: Bruker SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick 2008); program(s) used to refine structure: SHELXL2018/1 (Sheldrick, 2018); molecular graphics: Bruker SHELXTL; software used to prepare material for publication: Bruker SHELXTL.

(2R,3R)-3-(3-Hydroxyphenyl)-N,N,2-trimethylpentan-1-aminium (150K) top
Crystal data top
C14H24NO·ClF(000) = 560
Mr = 257.79Dx = 1.201 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 7.1062 (2) ÅCell parameters from 9942 reflections
b = 11.5821 (3) Åθ = 2.4–35.1°
c = 17.3894 (5) ŵ = 0.25 mm1
β = 94.9978 (11)°T = 150 K
V = 1425.79 (7) Å3Fragment, colourless
Z = 40.22 × 0.18 × 0.12 mm
Data collection top
Bruker APEX-II CCD
diffractometer
10087 reflections with I > 2σ(I)
φ and ω scansRint = 0.034
Absorption correction: multi-scan
Bruker SAINT
θmax = 35.3°, θmin = 2.4°
Tmin = 0.94, Tmax = 0.98h = 1111
21367 measured reflectionsk = 1818
11698 independent reflectionsl = 2727
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)] = 0.046 w = 1/[σ2(Fo2) + (0.0545P)2 + 0.4317P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.113(Δ/σ)max = 0.001
S = 1.03Δρmax = 0.40 e Å3
11698 reflectionsΔρmin = 0.32 e Å3
319 parametersAbsolute structure: Flack x determined using 4082 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
5 restraintsAbsolute structure parameter: 0.009 (15)
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
C1A0.2252 (3)0.53153 (17)0.77549 (11)0.0156 (3)
C2A0.1684 (3)0.42233 (18)0.79950 (13)0.0178 (4)
H2AA0.2105820.3946940.8494950.021*
C3A0.0503 (3)0.35451 (18)0.75007 (13)0.0195 (4)
H3AA0.0124540.2807530.7669990.023*
C4A0.0135 (3)0.3920 (2)0.67674 (13)0.0204 (4)
H4AA0.0935820.3445290.6435040.025*
C5A0.0423 (3)0.5008 (2)0.65262 (12)0.0187 (4)
C6A0.1605 (3)0.56937 (19)0.70149 (12)0.0178 (4)
H6AA0.1978040.6431050.6843390.021*
C7A0.3537 (3)0.60877 (18)0.82701 (12)0.0159 (3)
H7AA0.4086260.6657650.7919950.019*
C8A0.5232 (3)0.5431 (2)0.86810 (14)0.0211 (4)
H8AA0.5954640.5961670.9042410.025*
H8AB0.4755470.4790210.8987010.025*
C9A0.6538 (3)0.4946 (2)0.81147 (17)0.0281 (5)
H9AA0.7589040.4538620.8398710.042*
H9AB0.5834970.4408430.7762230.042*
H9AC0.7033910.5579670.7817620.042*
C10A0.2490 (3)0.68103 (17)0.88543 (12)0.0158 (3)
H10A0.3462490.7275940.9167800.019*
C11A0.1091 (4)0.7656 (2)0.84449 (14)0.0233 (4)
H11A0.1748840.8143730.8093560.035*
H11B0.0083530.7225580.8149890.035*
H11C0.0541420.8143030.8828600.035*
C12A0.1540 (3)0.60324 (18)0.94073 (13)0.0188 (4)
H12A0.0516060.5598700.9112280.023*
H12B0.2476500.5463570.9628470.023*
C13A0.0110 (4)0.5812 (2)1.05751 (16)0.0317 (5)
H13A0.1012120.5317881.0269910.048*
H13B0.0896910.5334221.0830660.048*
H13C0.0763810.6225401.0965310.048*
C14A0.2100 (4)0.7425 (3)1.05007 (16)0.0339 (6)
H14A0.2627010.7974531.0148220.051*
H14B0.1460010.7849091.0890420.051*
H14C0.3120720.6957921.0755770.051*
N1A0.0723 (3)0.66600 (17)1.00575 (11)0.0192 (3)
H1NA0.019 (3)0.709 (2)0.9870 (17)0.023*
O1A0.0218 (3)0.53470 (18)0.57942 (10)0.0295 (4)
H1OA0.043 (5)0.589 (2)0.562 (2)0.035*
C1B0.6929 (3)1.01289 (18)0.73270 (12)0.0163 (4)
C2B0.6185 (3)1.11833 (18)0.70472 (13)0.0188 (4)
H2BA0.6591131.1505190.6587060.023*
C3B0.4850 (3)1.17575 (19)0.74453 (14)0.0215 (4)
H3BA0.4342641.2468670.7249950.026*
C4B0.4246 (3)1.1311 (2)0.81221 (14)0.0216 (4)
H4BA0.3343601.1716760.8391010.026*
C5B0.4974 (3)1.0265 (2)0.84024 (12)0.0199 (4)
C6B0.6301 (3)0.96767 (19)0.80023 (12)0.0185 (4)
H6BA0.6783440.8957110.8193510.022*
C7B0.8437 (3)0.94833 (18)0.69268 (12)0.0162 (3)
H7BA0.9111880.8990580.7334800.019*
C8B0.9932 (3)1.0311 (2)0.66602 (14)0.0203 (4)
H8BA0.9327211.0822430.6254590.024*
H8BB1.0399131.0803500.7101390.024*
C9B1.1606 (4)0.9715 (2)0.63458 (17)0.0303 (5)
H9BA1.2496131.0296650.6187930.045*
H9BB1.2237610.9221690.6747280.045*
H9BC1.1164120.9240660.5899250.045*
C10B0.7626 (3)0.86337 (17)0.62906 (12)0.0151 (3)
H10B0.8721500.8235340.6082170.018*
C11B0.6390 (4)0.7704 (2)0.66121 (14)0.0232 (4)
H11D0.7110830.7300520.7037060.035*
H11E0.5272040.8063120.6802510.035*
H11F0.5995350.7150500.6203160.035*
C12B0.6588 (3)0.92956 (17)0.56259 (12)0.0169 (3)
H12C0.5526400.9723150.5825680.020*
H12D0.7462690.9871590.5433430.020*
C13B0.4928 (3)0.9309 (2)0.43327 (14)0.0247 (4)
H13D0.3982390.9807460.4542230.037*
H13E0.5899240.9787350.4122800.037*
H13F0.4316400.8825200.3921320.037*
C14B0.7267 (4)0.7787 (2)0.46636 (15)0.0268 (5)
H14D0.7830640.7304260.5085340.040*
H14E0.6669800.7294070.4254350.040*
H14F0.8252640.8256210.4455830.040*
N1B0.5821 (3)0.85576 (16)0.49599 (10)0.0162 (3)
H1NB0.493 (3)0.811 (2)0.5087 (17)0.019*
O1B0.4395 (3)0.98642 (17)0.90817 (11)0.0291 (4)
H1OB0.503 (5)0.927 (2)0.922 (2)0.035*
Cl1A0.22719 (7)0.71302 (4)0.50862 (3)0.02152 (11)
Cl1B0.71455 (7)0.81187 (4)0.98817 (3)0.02193 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.0153 (8)0.0161 (8)0.0156 (8)0.0010 (6)0.0026 (6)0.0015 (7)
C2A0.0185 (9)0.0163 (8)0.0187 (9)0.0017 (7)0.0024 (7)0.0011 (7)
C3A0.0197 (9)0.0159 (8)0.0237 (10)0.0007 (7)0.0063 (7)0.0027 (7)
C4A0.0178 (9)0.0232 (10)0.0206 (10)0.0033 (7)0.0032 (7)0.0054 (7)
C5A0.0164 (9)0.0250 (10)0.0147 (8)0.0025 (7)0.0014 (7)0.0010 (7)
C6A0.0171 (9)0.0206 (9)0.0159 (8)0.0031 (7)0.0021 (7)0.0000 (7)
C7A0.0152 (8)0.0170 (8)0.0155 (8)0.0001 (6)0.0011 (6)0.0008 (6)
C8A0.0158 (9)0.0230 (10)0.0241 (10)0.0037 (7)0.0004 (7)0.0015 (8)
C9A0.0191 (10)0.0279 (11)0.0382 (14)0.0054 (9)0.0071 (9)0.0013 (10)
C10A0.0169 (8)0.0142 (8)0.0162 (8)0.0020 (6)0.0006 (7)0.0011 (6)
C11A0.0257 (11)0.0206 (9)0.0231 (10)0.0087 (8)0.0003 (8)0.0021 (8)
C12A0.0217 (9)0.0158 (8)0.0197 (9)0.0035 (7)0.0063 (7)0.0010 (7)
C13A0.0327 (13)0.0345 (13)0.0302 (12)0.0080 (10)0.0164 (10)0.0090 (10)
C14A0.0356 (14)0.0428 (15)0.0223 (11)0.0028 (11)0.0026 (10)0.0112 (10)
N1A0.0182 (8)0.0214 (8)0.0180 (8)0.0055 (6)0.0024 (6)0.0007 (6)
O1A0.0285 (9)0.0409 (10)0.0177 (7)0.0134 (8)0.0055 (6)0.0053 (7)
C1B0.0143 (8)0.0179 (8)0.0161 (9)0.0026 (7)0.0013 (7)0.0031 (7)
C2B0.0181 (9)0.0183 (9)0.0198 (9)0.0029 (7)0.0002 (7)0.0001 (7)
C3B0.0209 (10)0.0191 (9)0.0242 (10)0.0059 (7)0.0006 (8)0.0019 (8)
C4B0.0180 (9)0.0231 (10)0.0237 (10)0.0074 (8)0.0012 (8)0.0030 (8)
C5B0.0175 (9)0.0240 (10)0.0179 (9)0.0037 (7)0.0001 (7)0.0007 (7)
C6B0.0189 (9)0.0194 (9)0.0169 (9)0.0048 (7)0.0006 (7)0.0006 (7)
C7B0.0139 (8)0.0183 (8)0.0158 (8)0.0034 (6)0.0024 (6)0.0019 (7)
C8B0.0130 (8)0.0208 (9)0.0268 (10)0.0010 (7)0.0001 (7)0.0066 (8)
C9B0.0198 (10)0.0313 (12)0.0408 (14)0.0015 (9)0.0084 (10)0.0097 (11)
C10B0.0145 (8)0.0143 (8)0.0160 (8)0.0005 (6)0.0009 (6)0.0003 (6)
C11B0.0278 (11)0.0194 (9)0.0220 (10)0.0053 (8)0.0009 (8)0.0039 (8)
C12B0.0190 (9)0.0155 (8)0.0157 (8)0.0006 (7)0.0025 (7)0.0003 (6)
C13B0.0222 (10)0.0302 (11)0.0204 (10)0.0028 (8)0.0056 (8)0.0061 (8)
C14B0.0253 (11)0.0337 (12)0.0218 (10)0.0050 (9)0.0032 (9)0.0081 (9)
N1B0.0138 (7)0.0197 (8)0.0151 (7)0.0021 (6)0.0003 (6)0.0001 (6)
O1B0.0291 (9)0.0356 (10)0.0239 (9)0.0126 (8)0.0096 (7)0.0051 (7)
Cl1A0.0191 (2)0.0181 (2)0.0271 (2)0.00398 (18)0.00062 (17)0.00143 (19)
Cl1B0.0196 (2)0.0190 (2)0.0271 (2)0.00380 (18)0.00135 (17)0.00214 (19)
Geometric parameters (Å, º) top
C1A—C6A1.399 (3)C1B—C6B1.394 (3)
C1A—C2A1.402 (3)C1B—C2B1.401 (3)
C1A—C7A1.515 (3)C1B—C7B1.523 (3)
C2A—C3A1.391 (3)C2B—C3B1.392 (3)
C2A—H2AA0.9500C2B—H2BA0.9500
C3A—C4A1.385 (3)C3B—C4B1.387 (3)
C3A—H3AA0.9500C3B—H3BA0.9500
C4A—C5A1.397 (3)C4B—C5B1.389 (3)
C4A—H4AA0.9500C4B—H4BA0.9500
C5A—O1A1.371 (3)C5B—O1B1.366 (3)
C5A—C6A1.391 (3)C5B—C6B1.397 (3)
C6A—H6AA0.9500C6B—H6BA0.9500
C7A—C8A1.546 (3)C7B—C8B1.532 (3)
C7A—C10A1.555 (3)C7B—C10B1.553 (3)
C7A—H7AA1.0000C7B—H7BA1.0000
C8A—C9A1.519 (3)C8B—C9B1.518 (3)
C8A—H8AA0.9900C8B—H8BA0.9900
C8A—H8AB0.9900C8B—H8BB0.9900
C9A—H9AA0.9800C9B—H9BA0.9800
C9A—H9AB0.9800C9B—H9BB0.9800
C9A—H9AC0.9800C9B—H9BC0.9800
C10A—C12A1.518 (3)C10B—C12B1.523 (3)
C10A—C11A1.527 (3)C10B—C11B1.526 (3)
C10A—H10A1.0000C10B—H10B1.0000
C11A—H11A0.9800C11B—H11D0.9800
C11A—H11B0.9800C11B—H11E0.9800
C11A—H11C0.9800C11B—H11F0.9800
C12A—N1A1.503 (3)C12B—N1B1.503 (3)
C12A—H12A0.9900C12B—H12C0.9900
C12A—H12B0.9900C12B—H12D0.9900
C13A—N1A1.489 (3)C13B—N1B1.493 (3)
C13A—H13A0.9800C13B—H13D0.9800
C13A—H13B0.9800C13B—H13E0.9800
C13A—H13C0.9800C13B—H13F0.9800
C14A—N1A1.485 (3)C14B—N1B1.486 (3)
C14A—H14A0.9800C14B—H14D0.9800
C14A—H14B0.9800C14B—H14E0.9800
C14A—H14C0.9800C14B—H14F0.9800
N1A—H1NA0.857 (13)N1B—H1NB0.864 (13)
O1A—H1OA0.843 (13)O1B—H1OB0.846 (13)
C6A—C1A—C2A118.45 (19)C6B—C1B—C2B118.77 (19)
C6A—C1A—C7A119.48 (18)C6B—C1B—C7B119.32 (18)
C2A—C1A—C7A122.07 (18)C2B—C1B—C7B121.89 (19)
C3A—C2A—C1A119.9 (2)C3B—C2B—C1B119.8 (2)
C3A—C2A—H2AA120.0C3B—C2B—H2BA120.1
C1A—C2A—H2AA120.0C1B—C2B—H2BA120.1
C4A—C3A—C2A121.6 (2)C4B—C3B—C2B121.3 (2)
C4A—C3A—H3AA119.2C4B—C3B—H3BA119.4
C2A—C3A—H3AA119.2C2B—C3B—H3BA119.4
C3A—C4A—C5A118.7 (2)C3B—C4B—C5B119.3 (2)
C3A—C4A—H4AA120.6C3B—C4B—H4BA120.4
C5A—C4A—H4AA120.6C5B—C4B—H4BA120.4
O1A—C5A—C6A122.5 (2)O1B—C5B—C4B118.0 (2)
O1A—C5A—C4A117.2 (2)O1B—C5B—C6B122.1 (2)
C6A—C5A—C4A120.3 (2)C4B—C5B—C6B119.9 (2)
C5A—C6A—C1A121.06 (19)C1B—C6B—C5B121.02 (19)
C5A—C6A—H6AA119.5C1B—C6B—H6BA119.5
C1A—C6A—H6AA119.5C5B—C6B—H6BA119.5
C1A—C7A—C8A112.83 (17)C1B—C7B—C8B111.39 (17)
C1A—C7A—C10A113.96 (17)C1B—C7B—C10B113.84 (16)
C8A—C7A—C10A111.14 (17)C8B—C7B—C10B113.87 (17)
C1A—C7A—H7AA106.1C1B—C7B—H7BA105.6
C8A—C7A—H7AA106.1C8B—C7B—H7BA105.6
C10A—C7A—H7AA106.1C10B—C7B—H7BA105.6
C9A—C8A—C7A112.19 (19)C9B—C8B—C7B114.21 (19)
C9A—C8A—H8AA109.2C9B—C8B—H8BA108.7
C7A—C8A—H8AA109.2C7B—C8B—H8BA108.7
C9A—C8A—H8AB109.2C9B—C8B—H8BB108.7
C7A—C8A—H8AB109.2C7B—C8B—H8BB108.7
H8AA—C8A—H8AB107.9H8BA—C8B—H8BB107.6
C8A—C9A—H9AA109.5C8B—C9B—H9BA109.5
C8A—C9A—H9AB109.5C8B—C9B—H9BB109.5
H9AA—C9A—H9AB109.5H9BA—C9B—H9BB109.5
C8A—C9A—H9AC109.5C8B—C9B—H9BC109.5
H9AA—C9A—H9AC109.5H9BA—C9B—H9BC109.5
H9AB—C9A—H9AC109.5H9BB—C9B—H9BC109.5
C12A—C10A—C11A111.64 (19)C12B—C10B—C11B112.17 (17)
C12A—C10A—C7A111.03 (16)C12B—C10B—C7B110.29 (16)
C11A—C10A—C7A111.72 (18)C11B—C10B—C7B112.07 (18)
C12A—C10A—H10A107.4C12B—C10B—H10B107.3
C11A—C10A—H10A107.4C11B—C10B—H10B107.3
C7A—C10A—H10A107.4C7B—C10B—H10B107.3
C10A—C11A—H11A109.5C10B—C11B—H11D109.5
C10A—C11A—H11B109.5C10B—C11B—H11E109.5
H11A—C11A—H11B109.5H11D—C11B—H11E109.5
C10A—C11A—H11C109.5C10B—C11B—H11F109.5
H11A—C11A—H11C109.5H11D—C11B—H11F109.5
H11B—C11A—H11C109.5H11E—C11B—H11F109.5
N1A—C12A—C10A114.32 (17)N1B—C12B—C10B114.69 (16)
N1A—C12A—H12A108.7N1B—C12B—H12C108.6
C10A—C12A—H12A108.7C10B—C12B—H12C108.6
N1A—C12A—H12B108.7N1B—C12B—H12D108.6
C10A—C12A—H12B108.7C10B—C12B—H12D108.6
H12A—C12A—H12B107.6H12C—C12B—H12D107.6
N1A—C13A—H13A109.5N1B—C13B—H13D109.5
N1A—C13A—H13B109.5N1B—C13B—H13E109.5
H13A—C13A—H13B109.5H13D—C13B—H13E109.5
N1A—C13A—H13C109.5N1B—C13B—H13F109.5
H13A—C13A—H13C109.5H13D—C13B—H13F109.5
H13B—C13A—H13C109.5H13E—C13B—H13F109.5
N1A—C14A—H14A109.5N1B—C14B—H14D109.5
N1A—C14A—H14B109.5N1B—C14B—H14E109.5
H14A—C14A—H14B109.5H14D—C14B—H14E109.5
N1A—C14A—H14C109.5N1B—C14B—H14F109.5
H14A—C14A—H14C109.5H14D—C14B—H14F109.5
H14B—C14A—H14C109.5H14E—C14B—H14F109.5
C14A—N1A—C13A111.0 (2)C14B—N1B—C13B111.05 (19)
C14A—N1A—C12A113.49 (19)C14B—N1B—C12B113.17 (17)
C13A—N1A—C12A109.61 (18)C13B—N1B—C12B109.51 (17)
C14A—N1A—H1NA107 (2)C14B—N1B—H1NB106 (2)
C13A—N1A—H1NA107 (2)C13B—N1B—H1NB105 (2)
C12A—N1A—H1NA109 (2)C12B—N1B—H1NB112 (2)
C5A—O1A—H1OA113 (3)C5B—O1B—H1OB109 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1NA···Cl1Bi0.86 (1)2.24 (2)3.0453 (19)156 (3)
O1A—H1OA···Cl1A0.84 (1)2.21 (1)3.0481 (19)173 (4)
N1B—H1NB···Cl1A0.86 (1)2.20 (2)3.0396 (19)163 (3)
O1B—H1OB···Cl1B0.85 (1)2.25 (2)3.0609 (19)161 (3)
Symmetry code: (i) x1, y, z.
(2R,3R)-3-(3-Hydroxyphenyl)-N,N,2-trimethylpentan-1-aminium (250K) top
Crystal data top
C14H24NO·ClF(000) = 560
Mr = 257.79Dx = 1.185 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 7.1350 (2) ÅCell parameters from 7469 reflections
b = 11.6402 (4) Åθ = 2.9–30.7°
c = 17.4546 (5) ŵ = 0.25 mm1
β = 94.7791 (14)°T = 250 K
V = 1444.61 (8) Å3Fragment, colourless
Z = 40.22 × 0.18 × 0.12 mm
Data collection top
Bruker APEX-II CCD
diffractometer
9197 reflections with I > 2σ(I)
φ and ω scansRint = 0.057
Absorption correction: multi-scan
Bruker SAINT
θmax = 35.2°, θmin = 2.3°
Tmin = 0.94, Tmax = 0.98h = 1111
21544 measured reflectionsk = 1818
11785 independent reflectionsl = 2727
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)] = 0.054 w = 1/[σ2(Fo2) + (0.0667P)2 + 0.3037P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.136(Δ/σ)max < 0.001
S = 1.04Δρmax = 0.34 e Å3
11785 reflectionsΔρmin = 0.33 e Å3
319 parametersAbsolute structure: Flack x determined using 3504 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
5 restraintsAbsolute structure parameter: 0.01 (5)
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
C1A0.2246 (3)0.5313 (2)0.77568 (14)0.0199 (4)
C2A0.1680 (4)0.4228 (2)0.79943 (16)0.0236 (5)
H2AA0.2094810.3955020.8486210.028*
C3A0.0502 (4)0.3552 (2)0.75029 (16)0.0257 (5)
H3AA0.0121890.2828080.7670850.031*
C4A0.0121 (4)0.3926 (2)0.67710 (16)0.0265 (5)
H4AA0.0903480.3457950.6442480.032*
C5A0.0433 (4)0.5006 (2)0.65312 (15)0.0241 (5)
C6A0.1609 (4)0.5691 (2)0.70177 (14)0.0228 (5)
H6AA0.1979380.6416180.6848150.027*
C7A0.3529 (3)0.6085 (2)0.82707 (14)0.0205 (4)
H7AA0.4071320.6645940.7924320.025*
C8A0.5219 (4)0.5432 (2)0.86785 (16)0.0268 (5)
H8AA0.5927140.5954610.9035100.032*
H8AB0.4749280.4799510.8979870.032*
C9A0.6527 (4)0.4952 (3)0.8115 (2)0.0370 (7)
H9AA0.7561110.4551550.8395280.055*
H9AB0.5839120.4421750.7767410.055*
H9AC0.7016790.5576650.7822630.055*
C10A0.2480 (4)0.6808 (2)0.88533 (14)0.0206 (4)
H10A0.3437520.7268360.9160140.025*
C11A0.1085 (4)0.7650 (2)0.84452 (17)0.0302 (6)
H11A0.1733800.8128450.8096910.045*
H11B0.0091990.7225130.8156590.045*
H11C0.0543700.8131280.8823530.045*
C12A0.1541 (4)0.6035 (2)0.94075 (15)0.0240 (5)
H12A0.0535450.5602810.9119120.029*
H12B0.2468050.5478640.9625950.029*
C13A0.0119 (5)0.5816 (3)1.0573 (2)0.0416 (8)
H13A0.1004720.5328771.0272970.062*
H13B0.0871060.5346551.0826300.062*
H13C0.0767610.6224941.0957100.062*
C14A0.2090 (6)0.7426 (3)1.0496 (2)0.0447 (8)
H14A0.2612460.7965301.0147520.067*
H14B0.1455430.7845541.0879490.067*
H14C0.3094100.6967141.0748690.067*
N1A0.0719 (3)0.6660 (2)1.00554 (13)0.0250 (4)
H1NA0.020 (4)0.708 (3)0.9880 (19)0.030*
O1A0.0203 (3)0.5346 (2)0.58002 (12)0.0381 (5)
H1OA0.040 (6)0.589 (3)0.561 (2)0.046*
C1B0.6938 (3)1.0129 (2)0.73271 (14)0.0209 (4)
C2B0.6191 (4)1.1178 (2)0.70489 (16)0.0244 (5)
H2BA0.6588891.1493670.6593960.029*
C3B0.4864 (4)1.1752 (2)0.74447 (17)0.0281 (5)
H3BA0.4362511.2450790.7250930.034*
C4B0.4265 (4)1.1310 (2)0.81220 (17)0.0277 (5)
H4BA0.3378171.1711870.8388110.033*
C5B0.4988 (4)1.0270 (2)0.84028 (15)0.0254 (5)
C6B0.6310 (4)0.9681 (2)0.80002 (15)0.0233 (5)
H6BA0.6780400.8971230.8187420.028*
C7B0.8434 (3)0.9486 (2)0.69249 (14)0.0207 (4)
H7BA0.9099900.9001030.7326380.025*
C8B0.9925 (4)1.0305 (2)0.66564 (17)0.0263 (5)
H8BA0.9332911.0804100.6253550.032*
H8BB1.0376841.0796370.7089130.032*
C9B1.1599 (5)0.9716 (3)0.6348 (2)0.0392 (7)
H9BA1.2474431.0290330.6191160.059*
H9BB1.2220640.9235930.6746820.059*
H9BC1.1175030.9243670.5909890.059*
C10B0.7625 (3)0.86362 (19)0.62917 (14)0.0189 (4)
H10B0.8705750.8245390.6083340.023*
C11B0.6396 (5)0.7708 (2)0.66139 (17)0.0297 (6)
H11D0.7106990.7310340.7031360.045*
H11E0.5293290.8060490.6803940.045*
H11F0.6006910.7163420.6210860.045*
C12B0.6583 (4)0.9294 (2)0.56308 (14)0.0218 (4)
H12C0.5534900.9712230.5830640.026*
H12D0.7440230.9864620.5439640.026*
C13B0.4920 (4)0.9305 (3)0.43400 (17)0.0326 (6)
H13D0.3990310.9796470.4549060.049*
H13E0.5873680.9774710.4128690.049*
H13F0.4312430.8826360.3937300.049*
C14B0.7250 (5)0.7792 (3)0.46666 (18)0.0348 (6)
H14D0.7810810.7317880.5081560.052*
H14E0.6657560.7304360.4265900.052*
H14F0.8218800.8252720.4457280.052*
N1B0.5818 (3)0.85580 (18)0.49649 (12)0.0209 (4)
H1NB0.495 (4)0.810 (3)0.5106 (18)0.025*
O1B0.4410 (3)0.9866 (2)0.90800 (13)0.0380 (5)
H1OB0.506 (6)0.929 (2)0.923 (2)0.046*
Cl1A0.22801 (9)0.71266 (5)0.50908 (4)0.02838 (14)
Cl1B0.71506 (9)0.81214 (5)0.98762 (4)0.02909 (14)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.0191 (10)0.0201 (10)0.0207 (10)0.0020 (8)0.0029 (8)0.0017 (8)
C2A0.0251 (12)0.0205 (10)0.0254 (11)0.0022 (9)0.0038 (9)0.0008 (9)
C3A0.0255 (12)0.0200 (10)0.0325 (13)0.0014 (9)0.0076 (10)0.0028 (9)
C4A0.0232 (12)0.0289 (12)0.0278 (13)0.0047 (9)0.0050 (10)0.0079 (10)
C5A0.0210 (11)0.0309 (12)0.0205 (11)0.0035 (9)0.0020 (9)0.0010 (9)
C6A0.0224 (11)0.0246 (11)0.0218 (11)0.0038 (9)0.0038 (9)0.0001 (8)
C7A0.0192 (10)0.0214 (10)0.0209 (10)0.0002 (8)0.0017 (8)0.0005 (8)
C8A0.0191 (11)0.0292 (12)0.0317 (13)0.0048 (9)0.0002 (9)0.0018 (10)
C9A0.0242 (14)0.0363 (15)0.0514 (19)0.0071 (11)0.0090 (13)0.0007 (13)
C10A0.0224 (11)0.0176 (9)0.0216 (11)0.0024 (8)0.0007 (8)0.0007 (8)
C11A0.0343 (15)0.0263 (12)0.0297 (14)0.0112 (11)0.0003 (11)0.0033 (10)
C12A0.0274 (12)0.0190 (10)0.0265 (12)0.0049 (9)0.0075 (9)0.0011 (8)
C13A0.0433 (19)0.0449 (17)0.0399 (17)0.0118 (14)0.0222 (14)0.0129 (14)
C14A0.0447 (19)0.057 (2)0.0318 (16)0.0019 (15)0.0023 (14)0.0163 (14)
N1A0.0235 (11)0.0279 (10)0.0236 (10)0.0078 (8)0.0027 (8)0.0013 (8)
O1A0.0382 (12)0.0510 (13)0.0239 (10)0.0175 (10)0.0055 (8)0.0069 (9)
C1B0.0181 (10)0.0231 (10)0.0212 (11)0.0035 (8)0.0007 (8)0.0042 (8)
C2B0.0231 (11)0.0234 (11)0.0266 (12)0.0036 (9)0.0003 (9)0.0000 (9)
C3B0.0280 (13)0.0223 (11)0.0335 (14)0.0077 (9)0.0005 (10)0.0017 (10)
C4B0.0229 (12)0.0282 (12)0.0320 (13)0.0090 (9)0.0018 (10)0.0047 (10)
C5B0.0233 (12)0.0304 (12)0.0223 (11)0.0052 (10)0.0006 (9)0.0022 (9)
C6B0.0231 (11)0.0246 (11)0.0218 (11)0.0068 (9)0.0009 (9)0.0018 (9)
C7B0.0168 (10)0.0236 (10)0.0212 (11)0.0044 (8)0.0023 (8)0.0021 (8)
C8B0.0161 (11)0.0267 (12)0.0359 (14)0.0016 (9)0.0002 (9)0.0086 (10)
C9B0.0262 (14)0.0399 (16)0.0532 (19)0.0039 (12)0.0124 (13)0.0136 (14)
C10B0.0186 (10)0.0173 (9)0.0205 (10)0.0011 (8)0.0006 (8)0.0000 (8)
C11B0.0351 (15)0.0245 (11)0.0290 (13)0.0080 (10)0.0002 (11)0.0051 (10)
C12B0.0239 (11)0.0184 (10)0.0225 (11)0.0015 (8)0.0021 (9)0.0002 (8)
C13B0.0302 (14)0.0387 (15)0.0272 (13)0.0053 (11)0.0084 (11)0.0091 (11)
C14B0.0343 (16)0.0425 (16)0.0277 (14)0.0053 (12)0.0039 (12)0.0114 (11)
N1B0.0187 (9)0.0237 (9)0.0199 (9)0.0038 (7)0.0007 (7)0.0002 (7)
O1B0.0384 (12)0.0455 (13)0.0319 (11)0.0159 (10)0.0133 (9)0.0062 (9)
Cl1A0.0251 (3)0.0230 (3)0.0369 (3)0.0057 (2)0.0016 (2)0.0021 (2)
Cl1B0.0254 (3)0.0245 (3)0.0373 (3)0.0051 (2)0.0024 (2)0.0030 (2)
Geometric parameters (Å, º) top
C1A—C2A1.400 (3)C1B—C6B1.393 (4)
C1A—C6A1.402 (3)C1B—C2B1.404 (3)
C1A—C7A1.521 (3)C1B—C7B1.522 (3)
C2A—C3A1.393 (4)C2B—C3B1.389 (4)
C2A—H2AA0.9400C2B—H2BA0.9400
C3A—C4A1.387 (4)C3B—C4B1.389 (4)
C3A—H3AA0.9400C3B—H3BA0.9400
C4A—C5A1.393 (4)C4B—C5B1.389 (4)
C4A—H4AA0.9400C4B—H4BA0.9400
C5A—O1A1.376 (3)C5B—O1B1.368 (3)
C5A—C6A1.393 (4)C5B—C6B1.402 (4)
C6A—H6AA0.9400C6B—H6BA0.9400
C7A—C8A1.548 (4)C7B—C8B1.531 (4)
C7A—C10A1.559 (4)C7B—C10B1.558 (3)
C7A—H7AA0.9900C7B—H7BA0.9900
C8A—C9A1.517 (4)C8B—C9B1.514 (4)
C8A—H8AA0.9800C8B—H8BA0.9800
C8A—H8AB0.9800C8B—H8BB0.9800
C9A—H9AA0.9700C9B—H9BA0.9700
C9A—H9AB0.9700C9B—H9BB0.9700
C9A—H9AC0.9700C9B—H9BC0.9700
C10A—C12A1.517 (4)C10B—C11B1.528 (4)
C10A—C11A1.530 (4)C10B—C12B1.526 (3)
C10A—H10A0.9900C10B—H10B0.9900
C11A—H11A0.9700C11B—H11D0.9700
C11A—H11B0.9700C11B—H11E0.9700
C11A—H11C0.9700C11B—H11F0.9700
C12A—N1A1.505 (3)C12B—N1B1.509 (3)
C12A—H12A0.9800C12B—H12C0.9800
C12A—H12B0.9800C12B—H12D0.9800
C13A—N1A1.493 (4)C13B—N1B1.496 (3)
C13A—H13A0.9700C13B—H13D0.9700
C13A—H13B0.9700C13B—H13E0.9700
C13A—H13C0.9700C13B—H13F0.9700
C14A—N1A1.489 (4)C14B—N1B1.483 (4)
C14A—H14A0.9700C14B—H14D0.9700
C14A—H14B0.9700C14B—H14E0.9700
C14A—H14C0.9700C14B—H14F0.9700
N1A—H1NA0.853 (13)N1B—H1NB0.867 (13)
O1A—H1OA0.844 (14)O1B—H1OB0.845 (13)
C2A—C1A—C6A118.4 (2)C6B—C1B—C2B118.5 (2)
C2A—C1A—C7A122.2 (2)C6B—C1B—C7B119.5 (2)
C6A—C1A—C7A119.4 (2)C2B—C1B—C7B121.9 (2)
C3A—C2A—C1A120.1 (2)C3B—C2B—C1B120.1 (3)
C3A—C2A—H2AA119.9C3B—C2B—H2BA119.9
C1A—C2A—H2AA119.9C1B—C2B—H2BA119.9
C4A—C3A—C2A121.4 (2)C4B—C3B—C2B121.1 (2)
C4A—C3A—H3AA119.3C4B—C3B—H3BA119.5
C2A—C3A—H3AA119.3C2B—C3B—H3BA119.5
C3A—C4A—C5A118.8 (2)C3B—C4B—C5B119.4 (2)
C3A—C4A—H4AA120.6C3B—C4B—H4BA120.3
C5A—C4A—H4AA120.6C5B—C4B—H4BA120.3
O1A—C5A—C6A122.4 (2)O1B—C5B—C4B118.4 (2)
O1A—C5A—C4A117.3 (2)O1B—C5B—C6B121.9 (2)
C6A—C5A—C4A120.3 (2)C4B—C5B—C6B119.7 (3)
C5A—C6A—C1A121.0 (2)C1B—C6B—C5B121.1 (2)
C5A—C6A—H6AA119.5C1B—C6B—H6BA119.4
C1A—C6A—H6AA119.5C5B—C6B—H6BA119.4
C1A—C7A—C8A112.9 (2)C1B—C7B—C8B111.5 (2)
C1A—C7A—C10A113.9 (2)C1B—C7B—C10B114.0 (2)
C8A—C7A—C10A111.3 (2)C8B—C7B—C10B113.8 (2)
C1A—C7A—H7AA106.0C1B—C7B—H7BA105.5
C8A—C7A—H7AA106.0C8B—C7B—H7BA105.5
C10A—C7A—H7AA106.0C10B—C7B—H7BA105.5
C9A—C8A—C7A112.4 (2)C9B—C8B—C7B114.5 (2)
C9A—C8A—H8AA109.1C9B—C8B—H8BA108.6
C7A—C8A—H8AA109.1C7B—C8B—H8BA108.6
C9A—C8A—H8AB109.1C9B—C8B—H8BB108.6
C7A—C8A—H8AB109.1C7B—C8B—H8BB108.6
H8AA—C8A—H8AB107.9H8BA—C8B—H8BB107.6
C8A—C9A—H9AA109.5C8B—C9B—H9BA109.5
C8A—C9A—H9AB109.5C8B—C9B—H9BB109.5
H9AA—C9A—H9AB109.5H9BA—C9B—H9BB109.5
C8A—C9A—H9AC109.5C8B—C9B—H9BC109.5
H9AA—C9A—H9AC109.5H9BA—C9B—H9BC109.5
H9AB—C9A—H9AC109.5H9BB—C9B—H9BC109.5
C12A—C10A—C11A111.8 (2)C11B—C10B—C12B112.0 (2)
C12A—C10A—C7A110.95 (19)C11B—C10B—C7B112.2 (2)
C11A—C10A—C7A111.8 (2)C12B—C10B—C7B110.24 (18)
C12A—C10A—H10A107.3C11B—C10B—H10B107.4
C11A—C10A—H10A107.3C12B—C10B—H10B107.4
C7A—C10A—H10A107.3C7B—C10B—H10B107.4
C10A—C11A—H11A109.5C10B—C11B—H11D109.5
C10A—C11A—H11B109.5C10B—C11B—H11E109.5
H11A—C11A—H11B109.5H11D—C11B—H11E109.5
C10A—C11A—H11C109.5C10B—C11B—H11F109.5
H11A—C11A—H11C109.5H11D—C11B—H11F109.5
H11B—C11A—H11C109.5H11E—C11B—H11F109.5
N1A—C12A—C10A114.4 (2)N1B—C12B—C10B114.79 (18)
N1A—C12A—H12A108.7N1B—C12B—H12C108.6
C10A—C12A—H12A108.7C10B—C12B—H12C108.6
N1A—C12A—H12B108.7N1B—C12B—H12D108.6
C10A—C12A—H12B108.7C10B—C12B—H12D108.6
H12A—C12A—H12B107.6H12C—C12B—H12D107.5
N1A—C13A—H13A109.5N1B—C13B—H13D109.5
N1A—C13A—H13B109.5N1B—C13B—H13E109.5
H13A—C13A—H13B109.5H13D—C13B—H13E109.5
N1A—C13A—H13C109.5N1B—C13B—H13F109.5
H13A—C13A—H13C109.5H13D—C13B—H13F109.5
H13B—C13A—H13C109.5H13E—C13B—H13F109.5
N1A—C14A—H14A109.5N1B—C14B—H14D109.5
N1A—C14A—H14B109.5N1B—C14B—H14E109.5
H14A—C14A—H14B109.5H14D—C14B—H14E109.5
N1A—C14A—H14C109.5N1B—C14B—H14F109.5
H14A—C14A—H14C109.5H14D—C14B—H14F109.5
H14B—C14A—H14C109.5H14E—C14B—H14F109.5
C14A—N1A—C13A111.1 (3)C14B—N1B—C13B111.0 (2)
C14A—N1A—C12A113.4 (2)C14B—N1B—C12B113.4 (2)
C13A—N1A—C12A109.7 (2)C13B—N1B—C12B109.7 (2)
C14A—N1A—H1NA107 (3)C14B—N1B—H1NB105 (2)
C13A—N1A—H1NA105 (3)C13B—N1B—H1NB107 (2)
C12A—N1A—H1NA110 (2)C12B—N1B—H1NB110 (2)
C5A—O1A—H1OA116 (3)C5B—O1B—H1OB110 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1NA···Cl1Bi0.85 (1)2.25 (2)3.056 (2)159 (3)
O1A—H1OA···Cl1A0.84 (1)2.22 (2)3.055 (2)172 (4)
N1B—H1NB···Cl1A0.87 (1)2.22 (2)3.048 (2)161 (3)
O1B—H1OB···Cl1B0.85 (1)2.25 (2)3.070 (2)163 (4)
Symmetry code: (i) x1, y, z.
(2R,3R)-3-(3-Hydroxyphenyl)-N,N,2-trimethylpentan-1-aminium (325K) top
Crystal data top
C14H24NO·ClDx = 1.160 Mg m3
Mr = 257.79Melting point: 477 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
a = 7.0653 (2) ÅCell parameters from 4830 reflections
b = 11.8351 (3) Åθ = 2.9–24.9°
c = 17.6593 (5) ŵ = 0.25 mm1
V = 1476.64 (7) Å3T = 325 K
Z = 4Fragment, colourless
F(000) = 5600.28 × 0.16 × 0.14 mm
Data collection top
Bruker APEX-II CCD
diffractometer
2216 reflections with I > 2σ(I)
φ and ω scansRint = 0.057
Absorption correction: multi-scan
Bruker SAINT
θmax = 26.4°, θmin = 2.1°
Tmin = 0.93, Tmax = 0.97h = 88
9587 measured reflectionsk = 1414
3015 independent reflectionsl = 1822
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)] = 0.045 w = 1/[σ2(Fo2) + (0.0512P)2 + 0.4533P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.103(Δ/σ)max < 0.001
S = 0.90Δρmax = 0.22 e Å3
3015 reflectionsΔρmin = 0.19 e Å3
164 parametersAbsolute structure: Flack x determined using 731 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
2 restraintsAbsolute structure parameter: 0.01 (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
C10.2309 (4)0.4870 (3)0.47040 (17)0.0397 (8)
C20.1820 (5)0.5952 (3)0.44499 (19)0.0472 (8)
H20.2228860.6198240.3977360.057*
C30.0741 (6)0.6649 (3)0.4894 (2)0.0544 (10)
H30.0442010.7368260.4719420.065*
C40.0089 (5)0.6310 (3)0.5593 (2)0.0532 (10)
H4A0.0649120.6791810.5886670.064*
C50.0550 (5)0.5243 (3)0.58520 (18)0.0493 (9)
C60.1663 (5)0.4537 (3)0.54110 (17)0.0439 (8)
H60.1982010.3824330.5593210.053*
C70.3525 (4)0.4071 (3)0.42299 (17)0.0418 (8)
H70.4081760.3537580.4591340.050*
C80.5211 (5)0.4656 (3)0.3845 (2)0.0558 (10)
H8A0.5868530.4108570.3531540.067*
H8B0.4737020.5246620.3514790.067*
C90.6590 (6)0.5162 (4)0.4391 (3)0.0773 (13)
H9A0.7668510.5443330.4119730.116*
H9B0.6991390.4595880.4745910.116*
H9C0.5994250.5772060.4659010.116*
C100.2393 (4)0.3341 (3)0.36671 (17)0.0419 (8)
H100.3307830.2872650.3392520.050*
C110.1024 (6)0.2541 (3)0.4064 (2)0.0624 (11)
H11A0.0501390.2024510.3700620.094*
H11B0.0022150.2969620.4292320.094*
H11C0.1687650.2125700.4447760.094*
C120.1396 (5)0.4073 (3)0.30852 (18)0.0462 (8)
H12A0.0424880.4510780.3339470.055*
H12B0.2304710.4600020.2874050.055*
C130.0424 (7)0.4225 (4)0.1913 (2)0.0735 (13)
H13A0.0998300.3805420.1508220.110*
H13B0.0507160.4731330.1708760.110*
H13C0.1377640.4651610.2174120.110*
C140.1824 (7)0.2654 (4)0.2052 (2)0.0742 (12)
H14A0.1212210.2347840.1612350.111*
H14B0.2179080.2049650.2385980.111*
H14C0.2933900.3063680.1901190.111*
N10.0501 (4)0.3429 (2)0.24513 (15)0.0463 (7)
H1N0.039 (4)0.302 (2)0.2630 (19)0.056*
O10.0106 (5)0.4938 (3)0.65487 (15)0.0740 (9)
H1O0.045 (6)0.439 (3)0.676 (2)0.089*
Cl10.19886 (13)0.30455 (7)0.73521 (5)0.0562 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0350 (17)0.0446 (18)0.0395 (18)0.0037 (14)0.0138 (14)0.0007 (14)
C20.053 (2)0.0425 (18)0.0456 (17)0.0059 (18)0.0105 (18)0.0031 (15)
C30.062 (2)0.043 (2)0.058 (2)0.0019 (18)0.0182 (19)0.0006 (17)
C40.050 (2)0.052 (2)0.058 (2)0.0143 (18)0.0135 (18)0.0125 (18)
C50.048 (2)0.063 (2)0.0367 (18)0.0113 (19)0.0087 (16)0.0024 (16)
C60.042 (2)0.0469 (18)0.0424 (18)0.0084 (16)0.0074 (16)0.0012 (15)
C70.0379 (19)0.0473 (18)0.0404 (17)0.0019 (15)0.0053 (14)0.0055 (15)
C80.039 (2)0.065 (2)0.064 (2)0.0082 (18)0.0008 (18)0.0028 (19)
C90.050 (3)0.085 (3)0.097 (3)0.016 (2)0.011 (2)0.006 (3)
C100.044 (2)0.0404 (18)0.0415 (17)0.0010 (14)0.0013 (14)0.0017 (13)
C110.078 (3)0.056 (2)0.053 (2)0.021 (2)0.006 (2)0.0121 (18)
C120.050 (2)0.0425 (18)0.0461 (18)0.0092 (16)0.0080 (16)0.0042 (16)
C130.079 (3)0.076 (3)0.065 (2)0.012 (3)0.030 (2)0.023 (2)
C140.070 (3)0.099 (3)0.054 (2)0.002 (3)0.009 (2)0.021 (2)
N10.0445 (16)0.0524 (16)0.0420 (16)0.0125 (13)0.0025 (13)0.0044 (12)
O10.080 (2)0.086 (2)0.0556 (17)0.0391 (16)0.0127 (15)0.0104 (15)
Cl10.0527 (5)0.0503 (5)0.0657 (5)0.0112 (4)0.0019 (5)0.0051 (4)
Geometric parameters (Å, º) top
C1—C61.387 (4)C9—H9C0.9600
C1—C21.400 (5)C10—C121.517 (4)
C1—C71.528 (5)C10—C111.524 (5)
C2—C31.370 (5)C10—H100.9800
C2—H20.9300C11—H11A0.9600
C3—C41.378 (5)C11—H11B0.9600
C3—H30.9300C11—H11C0.9600
C4—C51.382 (5)C12—N11.494 (4)
C4—H4A0.9300C12—H12A0.9700
C5—C61.387 (5)C12—H12B0.9700
C5—O11.363 (4)C13—N11.489 (5)
C6—H60.9300C13—H13A0.9600
C7—C101.541 (4)C13—H13B0.9600
C7—C81.536 (5)C13—H13C0.9600
C7—H70.9800C14—N11.487 (5)
C8—C91.497 (5)C14—H14A0.9600
C8—H8A0.9700C14—H14B0.9600
C8—H8B0.9700C14—H14C0.9600
C9—H9A0.9600N1—H1N0.856 (13)
C9—H9B0.9600O1—H1O0.846 (13)
C6—C1—C2117.9 (3)C7—C10—C11112.4 (3)
C6—C1—C7120.2 (3)C12—C10—C11111.8 (3)
C2—C1—C7122.0 (3)C7—C10—H10107.1
C3—C2—C1120.3 (3)C12—C10—H10107.1
C3—C2—H2119.9C11—C10—H10107.1
C1—C2—H2119.9C10—C11—H11A109.5
C4—C3—C2121.6 (3)C10—C11—H11B109.5
C4—C3—H3119.2H11A—C11—H11B109.5
C2—C3—H3119.2C10—C11—H11C109.5
C3—C4—C5118.9 (3)H11A—C11—H11C109.5
C3—C4—H4A120.6H11B—C11—H11C109.5
C5—C4—H4A120.6N1—C12—C10114.4 (3)
C6—C5—O1122.7 (3)N1—C12—H12A108.7
C6—C5—C4119.9 (3)C10—C12—H12A108.7
O1—C5—C4117.4 (3)N1—C12—H12B108.7
C5—C6—C1121.4 (3)C10—C12—H12B108.7
C5—C6—H6119.3H12A—C12—H12B107.6
C1—C6—H6119.3N1—C13—H13A109.5
C10—C7—C1114.1 (3)N1—C13—H13B109.5
C10—C7—C8111.7 (3)H13A—C13—H13B109.5
C1—C7—C8113.6 (3)N1—C13—H13C109.5
C10—C7—H7105.5H13A—C13—H13C109.5
C1—C7—H7105.5H13B—C13—H13C109.5
C8—C7—H7105.5N1—C14—H14A109.5
C9—C8—C7113.5 (3)N1—C14—H14B109.5
C9—C8—H8A108.9H14A—C14—H14B109.5
C7—C8—H8A108.9N1—C14—H14C109.5
C9—C8—H8B108.9H14A—C14—H14C109.5
C7—C8—H8B108.9H14B—C14—H14C109.5
H8A—C8—H8B107.7C14—N1—C12113.8 (3)
C8—C9—H9A109.5C14—N1—C13111.3 (3)
C8—C9—H9B109.5C12—N1—C13110.0 (3)
H9A—C9—H9B109.5C14—N1—H1N107 (2)
C8—C9—H9C109.5C12—N1—H1N109 (2)
H9A—C9—H9C109.5C13—N1—H1N106 (2)
H9B—C9—H9C109.5C5—O1—H1O117 (3)
C7—C10—C12111.0 (3)
C6—C1—C2—C30.2 (5)C6—C1—C7—C8137.2 (3)
C7—C1—C2—C3179.4 (3)C2—C1—C7—C842.4 (4)
C1—C2—C3—C40.8 (5)C10—C7—C8—C9167.3 (3)
C2—C3—C4—C50.5 (5)C1—C7—C8—C962.0 (4)
C3—C4—C5—C60.4 (5)C1—C7—C10—C1262.8 (3)
C3—C4—C5—O1179.5 (3)C8—C7—C10—C1267.7 (4)
O1—C5—C6—C1180.0 (3)C1—C7—C10—C1163.2 (4)
C4—C5—C6—C11.0 (5)C8—C7—C10—C11166.3 (3)
C2—C1—C6—C50.7 (5)C7—C10—C12—N1171.4 (3)
C7—C1—C6—C5179.7 (3)C11—C10—C12—N162.2 (4)
C6—C1—C7—C1093.3 (3)C10—C12—N1—C1454.0 (4)
C2—C1—C7—C1087.2 (4)C10—C12—N1—C13179.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···Cl1i0.86 (1)2.24 (2)3.054 (3)159 (3)
O1—H1O···Cl10.85 (1)2.19 (1)3.037 (3)177 (5)
Symmetry code: (i) x1/2, y+1/2, z+1.
 

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