Herein are reported the crystal and molecular structures of the pridinol mesylate salt (C20H25NO+·CH3O3S−) (I) and its monohydrated solvate form (C20H25NO+·CH3O3S−·H2O) (II). A comparison of both with the already reported structure of pure pridinol [1,1-diphenyl-3-piperidino-1-propanol, C20H25NO; Tacke et al. (1980). Chem. Ber. 113, 1962–1980] is made. Molecular structures (I) and (II) are alike in bond distances and bond angles, but differ in their spatial conformation, and, more relevant still, in their hydrogen-bonding motifs. This gives rise to quite different packing schemes, in the form of simple dimers in (I) but water-mediated hydrogen-bonded chains in (II). The dehydration behaviour of form (II) is highly dependent on the heating rate, with slow rates leading to a clear endothermic dehydration step, towards anhydrous (I), with subsequent melting of this latter phase. Increased heating rates result in a more unclear behaviour ending in a structural collapse (melting of the hydrated phase), at temperatures significantly lower than the melting point of the anhydrous phase. The eventual relevance of the water link in the structure of (II) is discussed in regard to this behaviour.
Supporting information
CCDC references: 1842103; 1842104
For both structures, data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009).
1,1-Diphenyl-3-piperidino-1-propanol, methanesulfonate. (I)
top
Crystal data top
C20H26NO·CH3O3S | F(000) = 840 |
Mr = 391.51 | Dx = 1.305 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.7198 (2) Å | Cell parameters from 1053 reflections |
b = 20.996 (8) Å | θ = 1.9–19.0° |
c = 10.9186 (3) Å | µ = 0.19 mm−1 |
β = 94.357 (2)° | T = 295 K |
V = 1993.2 (8) Å3 | Plate, colourless |
Z = 4 | 0.50 × 0.30 × 0.20 mm |
Data collection top
CCD Oxford Diffraction Xcalibur, Eos, Gemini diffractometer | 3300 reflections with I > 2σ(I) |
Radiation source: Enhance (Mo) X-ray Source | Rint = 0.018 |
thick slices scans | θmax = 28.3°, θmin = 3.7° |
Absorption correction: multi-scan CrysAlisPro (Oxford Diffraction, 2009) | h = −11→8 |
Tmin = 0.92, Tmax = 0.98 | k = −27→20 |
8157 measured reflections | l = −11→14 |
4393 independent reflections | |
Refinement top
Refinement on F2 | 2 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.045 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.117 | w = 1/[σ2(Fo2) + (0.0466P)2 + 0.5916P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
4393 reflections | Δρmax = 0.29 e Å−3 |
250 parameters | Δρmin = −0.31 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 | |
C1 | 0.7993 (3) | 0.43285 (10) | 0.83971 (18) | 0.0513 (5) | |
H1C | 0.910252 | 0.430099 | 0.838605 | 0.062* | |
H1D | 0.763681 | 0.394388 | 0.877768 | 0.062* | |
C2 | 0.7585 (3) | 0.48989 (12) | 0.9151 (2) | 0.0635 (6) | |
H2C | 0.648489 | 0.490435 | 0.922978 | 0.076* | |
H2D | 0.809858 | 0.486564 | 0.996845 | 0.076* | |
C3 | 0.8059 (3) | 0.55102 (12) | 0.8559 (2) | 0.0641 (6) | |
H3C | 0.917014 | 0.552476 | 0.854824 | 0.077* | |
H3D | 0.773587 | 0.587154 | 0.902983 | 0.077* | |
C4 | 0.7325 (3) | 0.55458 (10) | 0.7261 (2) | 0.0610 (6) | |
H4C | 0.621655 | 0.556732 | 0.728162 | 0.073* | |
H4D | 0.766429 | 0.593062 | 0.687031 | 0.073* | |
C5 | 0.7742 (3) | 0.49761 (10) | 0.6519 (2) | 0.0505 (5) | |
H5C | 0.723061 | 0.500600 | 0.570101 | 0.061* | |
H5D | 0.884307 | 0.497434 | 0.644180 | 0.061* | |
C6 | 0.7707 (2) | 0.37936 (10) | 0.63940 (19) | 0.0482 (5) | |
H6C | 0.760845 | 0.342011 | 0.690496 | 0.058* | |
H6D | 0.877747 | 0.382760 | 0.621762 | 0.058* | |
C7 | 0.6732 (2) | 0.36958 (9) | 0.51874 (18) | 0.0420 (4) | |
H7C | 0.608860 | 0.406806 | 0.502962 | 0.050* | |
H7D | 0.605891 | 0.333351 | 0.527546 | 0.050* | |
C8 | 0.7676 (2) | 0.35825 (8) | 0.40745 (17) | 0.0373 (4) | |
C9 | 0.88280 (19) | 0.30349 (9) | 0.42468 (16) | 0.0352 (4) | |
C10 | 0.8670 (2) | 0.25306 (9) | 0.50455 (18) | 0.0442 (5) | |
H10A | 0.788766 | 0.253776 | 0.557829 | 0.053* | |
C11 | 0.9665 (3) | 0.20161 (10) | 0.5060 (2) | 0.0535 (5) | |
H11A | 0.953942 | 0.168044 | 0.559915 | 0.064* | |
C12 | 1.0827 (2) | 0.19965 (11) | 0.4291 (2) | 0.0583 (6) | |
H12A | 1.148494 | 0.164773 | 0.429790 | 0.070* | |
C13 | 1.1014 (2) | 0.24965 (12) | 0.3506 (2) | 0.0586 (6) | |
H13A | 1.181233 | 0.248818 | 0.298822 | 0.070* | |
C14 | 1.0030 (2) | 0.30114 (10) | 0.34794 (19) | 0.0468 (5) | |
H14A | 1.017068 | 0.334645 | 0.294231 | 0.056* | |
C15 | 0.65935 (19) | 0.34173 (9) | 0.29390 (17) | 0.0372 (4) | |
C16 | 0.6477 (2) | 0.37973 (10) | 0.19027 (18) | 0.0458 (5) | |
H16A | 0.704300 | 0.417208 | 0.188585 | 0.055* | |
C17 | 0.5511 (2) | 0.36202 (13) | 0.0881 (2) | 0.0586 (6) | |
H17A | 0.542724 | 0.388074 | 0.019031 | 0.070* | |
C18 | 0.4683 (2) | 0.30638 (14) | 0.0889 (2) | 0.0635 (7) | |
H18A | 0.404474 | 0.294576 | 0.020545 | 0.076* | |
C19 | 0.4807 (2) | 0.26823 (12) | 0.1917 (2) | 0.0595 (6) | |
H19A | 0.424987 | 0.230493 | 0.192673 | 0.071* | |
C20 | 0.5750 (2) | 0.28551 (10) | 0.2931 (2) | 0.0481 (5) | |
H20A | 0.582299 | 0.259259 | 0.361870 | 0.058* | |
C22 | 0.2196 (2) | 0.37762 (10) | 0.5975 (2) | 0.0529 (5) | |
H22D | 0.296123 | 0.361697 | 0.546606 | 0.079* | |
H22E | 0.172497 | 0.342619 | 0.636970 | 0.079* | |
H22F | 0.142659 | 0.400518 | 0.547672 | 0.079* | |
N1 | 0.72876 (16) | 0.43703 (7) | 0.71045 (14) | 0.0376 (4) | |
H1N | 0.6313 (11) | 0.4366 (9) | 0.7123 (19) | 0.045* | |
O1 | 0.85704 (16) | 0.41395 (6) | 0.38839 (14) | 0.0484 (4) | |
H1O | 0.796 (2) | 0.4440 (8) | 0.368 (2) | 0.058* | |
O2 | 0.3745 (2) | 0.48005 (8) | 0.64260 (15) | 0.0712 (5) | |
O3 | 0.42502 (18) | 0.39267 (8) | 0.77640 (16) | 0.0725 (5) | |
O4 | 0.18663 (18) | 0.45063 (9) | 0.78127 (17) | 0.0787 (6) | |
S1 | 0.30671 (5) | 0.42895 (2) | 0.70953 (5) | 0.03967 (14) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0646 (13) | 0.0538 (13) | 0.0353 (11) | 0.0024 (10) | 0.0014 (9) | −0.0005 (10) |
C2 | 0.0744 (15) | 0.0743 (17) | 0.0422 (12) | −0.0042 (13) | 0.0068 (11) | −0.0186 (12) |
C3 | 0.0638 (14) | 0.0570 (14) | 0.0699 (16) | −0.0080 (11) | −0.0048 (12) | −0.0253 (13) |
C4 | 0.0692 (14) | 0.0418 (12) | 0.0703 (16) | −0.0048 (11) | −0.0064 (12) | −0.0085 (11) |
C5 | 0.0587 (12) | 0.0484 (12) | 0.0442 (12) | −0.0077 (10) | 0.0034 (9) | 0.0005 (10) |
C6 | 0.0553 (12) | 0.0464 (11) | 0.0428 (11) | 0.0141 (9) | 0.0033 (9) | −0.0078 (9) |
C7 | 0.0407 (9) | 0.0413 (11) | 0.0444 (11) | 0.0038 (8) | 0.0056 (8) | −0.0084 (9) |
C8 | 0.0388 (9) | 0.0327 (9) | 0.0405 (10) | −0.0036 (7) | 0.0042 (8) | −0.0018 (8) |
C9 | 0.0351 (9) | 0.0365 (9) | 0.0339 (9) | −0.0016 (7) | 0.0010 (7) | −0.0061 (8) |
C10 | 0.0485 (10) | 0.0418 (11) | 0.0433 (11) | 0.0021 (9) | 0.0093 (9) | −0.0026 (9) |
C11 | 0.0655 (13) | 0.0427 (12) | 0.0511 (13) | 0.0085 (10) | −0.0038 (11) | 0.0002 (10) |
C12 | 0.0507 (12) | 0.0555 (14) | 0.0665 (15) | 0.0173 (10) | −0.0088 (11) | −0.0149 (12) |
C13 | 0.0393 (10) | 0.0727 (16) | 0.0651 (15) | 0.0040 (10) | 0.0133 (10) | −0.0184 (13) |
C14 | 0.0429 (10) | 0.0541 (12) | 0.0442 (11) | −0.0042 (9) | 0.0087 (8) | −0.0039 (10) |
C15 | 0.0342 (9) | 0.0388 (10) | 0.0390 (10) | 0.0024 (7) | 0.0060 (7) | −0.0048 (8) |
C16 | 0.0467 (11) | 0.0472 (11) | 0.0437 (11) | 0.0034 (9) | 0.0049 (9) | −0.0008 (9) |
C17 | 0.0564 (13) | 0.0794 (17) | 0.0396 (12) | 0.0192 (12) | 0.0008 (9) | −0.0004 (12) |
C18 | 0.0384 (11) | 0.0942 (19) | 0.0566 (14) | 0.0086 (12) | −0.0046 (10) | −0.0313 (14) |
C19 | 0.0419 (11) | 0.0666 (15) | 0.0707 (16) | −0.0097 (10) | 0.0091 (10) | −0.0250 (13) |
C20 | 0.0446 (10) | 0.0485 (12) | 0.0516 (12) | −0.0075 (9) | 0.0066 (9) | −0.0058 (10) |
C22 | 0.0515 (12) | 0.0460 (12) | 0.0590 (14) | −0.0053 (9) | −0.0102 (10) | −0.0011 (10) |
N1 | 0.0329 (7) | 0.0414 (9) | 0.0387 (9) | 0.0009 (7) | 0.0046 (6) | −0.0064 (7) |
O1 | 0.0495 (8) | 0.0353 (7) | 0.0599 (9) | −0.0097 (6) | 0.0004 (7) | 0.0022 (7) |
O2 | 0.0898 (12) | 0.0643 (10) | 0.0603 (10) | −0.0386 (9) | 0.0118 (9) | −0.0007 (9) |
O3 | 0.0700 (10) | 0.0707 (11) | 0.0715 (11) | 0.0146 (9) | −0.0286 (8) | −0.0031 (9) |
O4 | 0.0560 (9) | 0.0948 (13) | 0.0885 (13) | 0.0015 (9) | 0.0269 (9) | −0.0285 (11) |
S1 | 0.0349 (2) | 0.0397 (3) | 0.0443 (3) | −0.00061 (19) | 0.00268 (19) | −0.0011 (2) |
Geometric parameters (Å, º) top
C1—N1 | 1.499 (2) | C10—H10A | 0.9300 |
C1—C2 | 1.511 (3) | C11—C12 | 1.365 (3) |
C1—H1C | 0.9700 | C11—H11A | 0.9300 |
C1—H1D | 0.9700 | C12—C13 | 1.372 (3) |
C2—C3 | 1.509 (3) | C12—H12A | 0.9300 |
C2—H2C | 0.9700 | C13—C14 | 1.379 (3) |
C2—H2D | 0.9700 | C13—H13A | 0.9300 |
C3—C4 | 1.513 (3) | C14—H14A | 0.9300 |
C3—H3C | 0.9700 | C15—C16 | 1.382 (3) |
C3—H3D | 0.9700 | C15—C20 | 1.391 (3) |
C4—C5 | 1.504 (3) | C16—C17 | 1.396 (3) |
C4—H4C | 0.9700 | C16—H16A | 0.9300 |
C4—H4D | 0.9700 | C17—C18 | 1.373 (3) |
C5—N1 | 1.491 (3) | C17—H17A | 0.9300 |
C5—H5C | 0.9700 | C18—C19 | 1.377 (4) |
C5—H5D | 0.9700 | C18—H18A | 0.9300 |
C6—N1 | 1.498 (2) | C19—C20 | 1.376 (3) |
C6—C7 | 1.526 (3) | C19—H19A | 0.9300 |
C6—H6C | 0.9700 | C20—H20A | 0.9300 |
C6—H6D | 0.9700 | C22—S1 | 1.759 (2) |
C7—C8 | 1.537 (3) | C22—H22D | 0.9600 |
C7—H7C | 0.9700 | C22—H22E | 0.9600 |
C7—H7D | 0.9700 | C22—H22F | 0.9600 |
C8—O1 | 1.430 (2) | N1—H1N | 0.852 (9) |
C8—C9 | 1.529 (2) | O1—H1O | 0.843 (9) |
C8—C15 | 1.540 (2) | O2—S1 | 1.4492 (16) |
C9—C10 | 1.385 (3) | O3—S1 | 1.4364 (15) |
C9—C14 | 1.391 (3) | O4—S1 | 1.4289 (16) |
C10—C11 | 1.384 (3) | | |
| | | |
N1—C1—C2 | 111.71 (18) | C11—C10—H10A | 119.6 |
N1—C1—H1C | 109.3 | C9—C10—H10A | 119.6 |
C2—C1—H1C | 109.3 | C12—C11—C10 | 120.7 (2) |
N1—C1—H1D | 109.3 | C12—C11—H11A | 119.7 |
C2—C1—H1D | 109.3 | C10—C11—H11A | 119.7 |
H1C—C1—H1D | 107.9 | C11—C12—C13 | 119.3 (2) |
C3—C2—C1 | 110.95 (19) | C11—C12—H12A | 120.3 |
C3—C2—H2C | 109.4 | C13—C12—H12A | 120.3 |
C1—C2—H2C | 109.4 | C12—C13—C14 | 120.6 (2) |
C3—C2—H2D | 109.4 | C12—C13—H13A | 119.7 |
C1—C2—H2D | 109.4 | C14—C13—H13A | 119.7 |
H2C—C2—H2D | 108.0 | C13—C14—C9 | 120.7 (2) |
C2—C3—C4 | 109.47 (19) | C13—C14—H14A | 119.6 |
C2—C3—H3C | 109.8 | C9—C14—H14A | 119.6 |
C4—C3—H3C | 109.8 | C16—C15—C20 | 118.59 (19) |
C2—C3—H3D | 109.8 | C16—C15—C8 | 122.13 (17) |
C4—C3—H3D | 109.8 | C20—C15—C8 | 119.22 (17) |
H3C—C3—H3D | 108.2 | C15—C16—C17 | 120.2 (2) |
C5—C4—C3 | 111.3 (2) | C15—C16—H16A | 119.9 |
C5—C4—H4C | 109.4 | C17—C16—H16A | 119.9 |
C3—C4—H4C | 109.4 | C18—C17—C16 | 120.5 (2) |
C5—C4—H4D | 109.4 | C18—C17—H17A | 119.8 |
C3—C4—H4D | 109.4 | C16—C17—H17A | 119.8 |
H4C—C4—H4D | 108.0 | C17—C18—C19 | 119.4 (2) |
N1—C5—C4 | 111.41 (17) | C17—C18—H18A | 120.3 |
N1—C5—H5C | 109.3 | C19—C18—H18A | 120.3 |
C4—C5—H5C | 109.3 | C20—C19—C18 | 120.5 (2) |
N1—C5—H5D | 109.3 | C20—C19—H19A | 119.7 |
C4—C5—H5D | 109.3 | C18—C19—H19A | 119.7 |
H5C—C5—H5D | 108.0 | C19—C20—C15 | 120.8 (2) |
N1—C6—C7 | 114.45 (16) | C19—C20—H20A | 119.6 |
N1—C6—H6C | 108.6 | C15—C20—H20A | 119.6 |
C7—C6—H6C | 108.6 | S1—C22—H22D | 109.5 |
N1—C6—H6D | 108.6 | S1—C22—H22E | 109.5 |
C7—C6—H6D | 108.6 | H22D—C22—H22E | 109.5 |
H6C—C6—H6D | 107.6 | S1—C22—H22F | 109.5 |
C6—C7—C8 | 113.99 (15) | H22D—C22—H22F | 109.5 |
C6—C7—H7C | 108.8 | H22E—C22—H22F | 109.5 |
C8—C7—H7C | 108.8 | C5—N1—C6 | 112.61 (15) |
C6—C7—H7D | 108.8 | C5—N1—C1 | 110.49 (16) |
C8—C7—H7D | 108.8 | C6—N1—C1 | 109.97 (15) |
H7C—C7—H7D | 107.6 | C5—N1—H1N | 108.5 (14) |
O1—C8—C9 | 105.80 (14) | C6—N1—H1N | 106.7 (14) |
O1—C8—C7 | 108.63 (15) | C1—N1—H1N | 108.4 (14) |
C9—C8—C7 | 113.91 (15) | C8—O1—H1O | 108.2 (16) |
O1—C8—C15 | 112.02 (15) | O4—S1—O3 | 114.72 (12) |
C9—C8—C15 | 106.65 (14) | O4—S1—O2 | 112.61 (12) |
C7—C8—C15 | 109.83 (14) | O3—S1—O2 | 110.14 (11) |
C10—C9—C14 | 117.86 (17) | O4—S1—C22 | 106.31 (11) |
C10—C9—C8 | 123.82 (16) | O3—S1—C22 | 106.51 (10) |
C14—C9—C8 | 118.07 (17) | O2—S1—C22 | 105.90 (10) |
C11—C10—C9 | 120.78 (19) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···O2i | 0.84 (1) | 2.18 (1) | 3.007 (3) | 167 (2) |
N1—H1N···O3 | 0.85 (1) | 2.18 (1) | 2.948 (2) | 149 (2) |
N1—H1N···O2 | 0.85 (1) | 2.48 (1) | 3.250 (2) | 150 (2) |
C5—H5C···O2i | 0.97 | 2.45 | 3.407 (3) | 171 |
Symmetry code: (i) −x+1, −y+1, −z+1. |
1,1-Diphenyl-3-piperidino-1-propanol, methanesulfonate, hydrate. (II)
top
Crystal data top
C20H26NO·CH3O3S·H2O | F(000) = 880 |
Mr = 409.53 | Dx = 1.228 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 8.2086 (2) Å | Cell parameters from 2641 reflections |
b = 17.9355 (6) Å | θ = 4.4–27.7° |
c = 15.0983 (5) Å | µ = 0.18 mm−1 |
β = 94.770 (2)° | T = 295 K |
V = 2215.15 (12) Å3 | Plate, colourless |
Z = 4 | 0.50 × 0.30 × 0.18 mm |
Data collection top
CCD Oxford Diffraction Xcalibur, Eos, Gemini diffractometer | 3559 reflections with I > 2σ(I) |
Radiation source: Enhance (Mo) X-ray Source | Rint = 0.022 |
thick slices scans | θmax = 28.3°, θmin = 3.6° |
Absorption correction: multi-scan CrysAlisPro (Oxford Diffraction, 2009) | h = −5→10 |
Tmin = 0.91, Tmax = 0.98 | k = −17→23 |
9717 measured reflections | l = −19→19 |
4896 independent reflections | |
Refinement top
Refinement on F2 | 5 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.051 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.133 | w = 1/[σ2(Fo2) + (0.0509P)2 + 0.6627P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
4896 reflections | Δρmax = 0.33 e Å−3 |
266 parameters | Δρmin = −0.29 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 | |
C1 | 0.4705 (3) | 0.86122 (12) | 0.72728 (12) | 0.0576 (5) | |
H1A | 0.567941 | 0.836122 | 0.752904 | 0.069* | |
H1B | 0.376981 | 0.830010 | 0.736735 | 0.069* | |
C2 | 0.4528 (3) | 0.93521 (13) | 0.77292 (14) | 0.0711 (7) | |
H2A | 0.351104 | 0.958508 | 0.750352 | 0.085* | |
H2B | 0.448391 | 0.927105 | 0.836194 | 0.085* | |
C3 | 0.5931 (4) | 0.98648 (15) | 0.75798 (17) | 0.0820 (8) | |
H3A | 0.694030 | 0.965629 | 0.785415 | 0.098* | |
H3B | 0.575649 | 1.034498 | 0.785201 | 0.098* | |
C4 | 0.6064 (3) | 0.99653 (13) | 0.65844 (16) | 0.0690 (6) | |
H4A | 0.510341 | 1.022537 | 0.632537 | 0.083* | |
H4B | 0.701385 | 1.026836 | 0.649233 | 0.083* | |
C5 | 0.6212 (3) | 0.92216 (12) | 0.61229 (15) | 0.0593 (5) | |
H5A | 0.622438 | 0.930168 | 0.548812 | 0.071* | |
H5B | 0.723486 | 0.898630 | 0.633424 | 0.071* | |
C6 | 0.4901 (3) | 0.79772 (10) | 0.58494 (12) | 0.0476 (4) | |
H6A | 0.406093 | 0.765660 | 0.605768 | 0.057* | |
H6B | 0.595163 | 0.775047 | 0.602395 | 0.057* | |
C7 | 0.4677 (2) | 0.80159 (10) | 0.48413 (12) | 0.0431 (4) | |
H7A | 0.545682 | 0.836532 | 0.462747 | 0.052* | |
H7B | 0.358576 | 0.819382 | 0.465655 | 0.052* | |
C8 | 0.4932 (2) | 0.72403 (10) | 0.44338 (12) | 0.0419 (4) | |
C9 | 0.3735 (2) | 0.66762 (10) | 0.47737 (11) | 0.0437 (4) | |
C10 | 0.2067 (2) | 0.68129 (12) | 0.46608 (14) | 0.0529 (5) | |
H10 | 0.168768 | 0.724136 | 0.436406 | 0.063* | |
C11 | 0.0963 (3) | 0.63239 (14) | 0.49813 (15) | 0.0668 (6) | |
H11 | −0.014915 | 0.642925 | 0.490683 | 0.080* | |
C12 | 0.1487 (4) | 0.56877 (16) | 0.54062 (17) | 0.0785 (8) | |
H12 | 0.073877 | 0.535903 | 0.562224 | 0.094* | |
C13 | 0.3129 (4) | 0.55358 (13) | 0.55127 (16) | 0.0810 (8) | |
H13 | 0.348779 | 0.509789 | 0.579533 | 0.097* | |
C14 | 0.4269 (3) | 0.60287 (12) | 0.52033 (14) | 0.0625 (6) | |
H14 | 0.538050 | 0.592260 | 0.528536 | 0.075* | |
C15 | 0.4740 (2) | 0.72592 (11) | 0.34140 (12) | 0.0438 (4) | |
C16 | 0.5292 (3) | 0.66553 (14) | 0.29558 (14) | 0.0621 (6) | |
H16 | 0.572911 | 0.624709 | 0.327230 | 0.074* | |
C17 | 0.5209 (3) | 0.66441 (17) | 0.20395 (17) | 0.0754 (7) | |
H17 | 0.558898 | 0.623142 | 0.174581 | 0.091* | |
C18 | 0.4569 (3) | 0.72373 (17) | 0.15634 (15) | 0.0737 (7) | |
H18 | 0.454234 | 0.723736 | 0.094644 | 0.088* | |
C19 | 0.3968 (4) | 0.78320 (15) | 0.20009 (16) | 0.0782 (8) | |
H19 | 0.350494 | 0.823120 | 0.167743 | 0.094* | |
C20 | 0.4043 (3) | 0.78458 (13) | 0.29213 (14) | 0.0630 (6) | |
H20 | 0.362184 | 0.825188 | 0.320984 | 0.076* | |
O1W | 0.2132 (2) | 0.94528 (9) | 0.55574 (11) | 0.0708 (5) | |
H1WA | 0.164 (3) | 0.9261 (11) | 0.5092 (11) | 0.085* | |
H1WB | 0.205 (3) | 0.9918 (6) | 0.5655 (15) | 0.085* | |
N1 | 0.48207 (18) | 0.87173 (8) | 0.62950 (10) | 0.0420 (4) | |
H1N | 0.3950 (16) | 0.8941 (10) | 0.6087 (12) | 0.050* | |
O1 | 0.65420 (16) | 0.69873 (8) | 0.47165 (10) | 0.0554 (4) | |
H1O | 0.718 (2) | 0.7294 (11) | 0.4499 (14) | 0.066* | |
C21 | 0.8881 (5) | 0.8687 (2) | 0.26254 (19) | 0.1288 (14) | |
H21A | 0.970099 | 0.839861 | 0.236277 | 0.193* | |
H21B | 0.899670 | 0.920274 | 0.247237 | 0.193* | |
H21C | 0.781636 | 0.851422 | 0.240647 | 0.193* | |
O2 | 0.8839 (2) | 0.78038 (10) | 0.39176 (15) | 0.0914 (6) | |
O3 | 1.07687 (19) | 0.88089 (11) | 0.40318 (12) | 0.0866 (6) | |
O4 | 0.7905 (2) | 0.90468 (10) | 0.41258 (14) | 0.0916 (6) | |
S1 | 0.91163 (6) | 0.85887 (3) | 0.37680 (3) | 0.05261 (17) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0803 (15) | 0.0543 (12) | 0.0380 (10) | 0.0023 (11) | 0.0033 (9) | 0.0027 (9) |
C2 | 0.1085 (19) | 0.0629 (15) | 0.0431 (12) | 0.0032 (14) | 0.0131 (12) | −0.0085 (10) |
C3 | 0.109 (2) | 0.0682 (16) | 0.0666 (15) | −0.0065 (15) | −0.0060 (14) | −0.0274 (13) |
C4 | 0.0800 (15) | 0.0543 (14) | 0.0739 (15) | −0.0183 (12) | 0.0133 (12) | −0.0159 (12) |
C5 | 0.0569 (12) | 0.0586 (13) | 0.0635 (13) | −0.0118 (10) | 0.0127 (10) | −0.0120 (11) |
C6 | 0.0631 (12) | 0.0374 (10) | 0.0417 (10) | 0.0033 (9) | 0.0016 (8) | −0.0028 (8) |
C7 | 0.0476 (10) | 0.0389 (10) | 0.0424 (10) | 0.0004 (8) | 0.0014 (7) | −0.0005 (8) |
C8 | 0.0414 (9) | 0.0417 (10) | 0.0422 (10) | 0.0053 (8) | 0.0018 (7) | −0.0013 (8) |
C9 | 0.0601 (11) | 0.0354 (9) | 0.0359 (9) | 0.0014 (8) | 0.0060 (8) | −0.0057 (7) |
C10 | 0.0556 (12) | 0.0493 (12) | 0.0543 (12) | −0.0041 (9) | 0.0077 (9) | −0.0022 (9) |
C11 | 0.0689 (14) | 0.0730 (16) | 0.0600 (14) | −0.0198 (12) | 0.0140 (11) | −0.0111 (12) |
C12 | 0.107 (2) | 0.0698 (17) | 0.0608 (15) | −0.0339 (16) | 0.0223 (14) | −0.0084 (13) |
C13 | 0.137 (3) | 0.0439 (13) | 0.0629 (16) | −0.0052 (15) | 0.0142 (15) | 0.0106 (11) |
C14 | 0.0854 (16) | 0.0438 (12) | 0.0588 (13) | 0.0101 (11) | 0.0092 (11) | 0.0040 (10) |
C15 | 0.0421 (9) | 0.0478 (11) | 0.0419 (10) | −0.0041 (8) | 0.0056 (7) | −0.0027 (8) |
C16 | 0.0621 (13) | 0.0709 (15) | 0.0535 (12) | 0.0153 (11) | 0.0065 (10) | −0.0126 (11) |
C17 | 0.0647 (14) | 0.102 (2) | 0.0606 (14) | 0.0054 (14) | 0.0136 (11) | −0.0270 (15) |
C18 | 0.0769 (16) | 0.103 (2) | 0.0419 (12) | −0.0273 (15) | 0.0097 (11) | −0.0064 (13) |
C19 | 0.115 (2) | 0.0678 (16) | 0.0496 (13) | −0.0153 (15) | −0.0077 (13) | 0.0082 (12) |
C20 | 0.0911 (16) | 0.0507 (13) | 0.0457 (11) | −0.0023 (12) | −0.0030 (10) | −0.0007 (10) |
O1W | 0.0820 (11) | 0.0566 (10) | 0.0699 (11) | 0.0106 (9) | −0.0179 (8) | −0.0002 (8) |
N1 | 0.0461 (8) | 0.0412 (9) | 0.0385 (8) | 0.0023 (7) | 0.0022 (6) | −0.0011 (7) |
O1 | 0.0460 (8) | 0.0608 (9) | 0.0584 (9) | 0.0111 (6) | −0.0009 (6) | 0.0008 (7) |
C21 | 0.164 (4) | 0.158 (4) | 0.0613 (18) | 0.009 (3) | −0.0067 (19) | −0.002 (2) |
O2 | 0.0668 (11) | 0.0640 (11) | 0.1443 (18) | 0.0027 (9) | 0.0151 (11) | 0.0202 (11) |
O3 | 0.0547 (9) | 0.1091 (15) | 0.0957 (13) | −0.0199 (9) | 0.0043 (8) | −0.0202 (11) |
O4 | 0.0735 (11) | 0.0718 (12) | 0.1349 (17) | −0.0015 (9) | 0.0398 (11) | −0.0285 (11) |
S1 | 0.0459 (3) | 0.0577 (3) | 0.0540 (3) | −0.0005 (2) | 0.0028 (2) | −0.0055 (2) |
Geometric parameters (Å, º) top
C1—N1 | 1.499 (2) | C11—C12 | 1.361 (4) |
C1—C2 | 1.508 (3) | C11—H11 | 0.9300 |
C1—H1A | 0.9700 | C12—C13 | 1.371 (4) |
C1—H1B | 0.9700 | C12—H12 | 0.9300 |
C2—C3 | 1.505 (4) | C13—C14 | 1.396 (4) |
C2—H2A | 0.9700 | C13—H13 | 0.9300 |
C2—H2B | 0.9700 | C14—H14 | 0.9300 |
C3—C4 | 1.527 (3) | C15—C16 | 1.382 (3) |
C3—H3A | 0.9700 | C15—C20 | 1.385 (3) |
C3—H3B | 0.9700 | C16—C17 | 1.380 (3) |
C4—C5 | 1.514 (3) | C16—H16 | 0.9300 |
C4—H4A | 0.9700 | C17—C18 | 1.364 (4) |
C4—H4B | 0.9700 | C17—H17 | 0.9300 |
C5—N1 | 1.496 (2) | C18—C19 | 1.368 (4) |
C5—H5A | 0.9700 | C18—H18 | 0.9300 |
C5—H5B | 0.9700 | C19—C20 | 1.386 (3) |
C6—N1 | 1.492 (2) | C19—H19 | 0.9300 |
C6—C7 | 1.519 (2) | C20—H20 | 0.9300 |
C6—H6A | 0.9700 | O1W—H1WA | 0.854 (9) |
C6—H6B | 0.9700 | O1W—H1WB | 0.851 (9) |
C7—C8 | 1.542 (2) | N1—H1N | 0.856 (9) |
C7—H7A | 0.9700 | O1—H1O | 0.843 (10) |
C7—H7B | 0.9700 | C21—S1 | 1.729 (3) |
C8—O1 | 1.428 (2) | C21—H21A | 0.9600 |
C8—C9 | 1.529 (3) | C21—H21B | 0.9600 |
C8—C15 | 1.535 (2) | C21—H21C | 0.9600 |
C9—C14 | 1.384 (3) | O2—S1 | 1.4468 (18) |
C9—C10 | 1.388 (3) | O3—S1 | 1.4369 (16) |
C10—C11 | 1.377 (3) | O4—S1 | 1.4303 (17) |
C10—H10 | 0.9300 | | |
| | | |
N1—C1—C2 | 110.84 (17) | C11—C10—H10 | 119.5 |
N1—C1—H1A | 109.5 | C9—C10—H10 | 119.5 |
C2—C1—H1A | 109.5 | C12—C11—C10 | 120.5 (2) |
N1—C1—H1B | 109.5 | C12—C11—H11 | 119.7 |
C2—C1—H1B | 109.5 | C10—C11—H11 | 119.7 |
H1A—C1—H1B | 108.1 | C11—C12—C13 | 119.4 (2) |
C3—C2—C1 | 111.4 (2) | C11—C12—H12 | 120.3 |
C3—C2—H2A | 109.3 | C13—C12—H12 | 120.3 |
C1—C2—H2A | 109.3 | C12—C13—C14 | 121.0 (2) |
C3—C2—H2B | 109.3 | C12—C13—H13 | 119.5 |
C1—C2—H2B | 109.3 | C14—C13—H13 | 119.5 |
H2A—C2—H2B | 108.0 | C9—C14—C13 | 119.5 (2) |
C2—C3—C4 | 109.75 (19) | C9—C14—H14 | 120.2 |
C2—C3—H3A | 109.7 | C13—C14—H14 | 120.2 |
C4—C3—H3A | 109.7 | C16—C15—C20 | 117.69 (19) |
C2—C3—H3B | 109.7 | C16—C15—C8 | 118.32 (18) |
C4—C3—H3B | 109.7 | C20—C15—C8 | 124.00 (17) |
H3A—C3—H3B | 108.2 | C17—C16—C15 | 121.5 (2) |
C5—C4—C3 | 111.3 (2) | C17—C16—H16 | 119.2 |
C5—C4—H4A | 109.4 | C15—C16—H16 | 119.2 |
C3—C4—H4A | 109.4 | C18—C17—C16 | 120.1 (2) |
C5—C4—H4B | 109.4 | C18—C17—H17 | 119.9 |
C3—C4—H4B | 109.4 | C16—C17—H17 | 119.9 |
H4A—C4—H4B | 108.0 | C17—C18—C19 | 119.5 (2) |
N1—C5—C4 | 111.17 (17) | C17—C18—H18 | 120.3 |
N1—C5—H5A | 109.4 | C19—C18—H18 | 120.3 |
C4—C5—H5A | 109.4 | C18—C19—C20 | 120.7 (2) |
N1—C5—H5B | 109.4 | C18—C19—H19 | 119.7 |
C4—C5—H5B | 109.4 | C20—C19—H19 | 119.7 |
H5A—C5—H5B | 108.0 | C15—C20—C19 | 120.5 (2) |
N1—C6—C7 | 113.88 (15) | C15—C20—H20 | 119.8 |
N1—C6—H6A | 108.8 | C19—C20—H20 | 119.8 |
C7—C6—H6A | 108.8 | H1WA—O1W—H1WB | 119.8 (16) |
N1—C6—H6B | 108.8 | C6—N1—C5 | 113.37 (15) |
C7—C6—H6B | 108.8 | C6—N1—C1 | 109.93 (14) |
H6A—C6—H6B | 107.7 | C5—N1—C1 | 111.03 (15) |
C6—C7—C8 | 110.45 (15) | C6—N1—H1N | 108.6 (14) |
C6—C7—H7A | 109.6 | C5—N1—H1N | 106.2 (14) |
C8—C7—H7A | 109.6 | C1—N1—H1N | 107.5 (13) |
C6—C7—H7B | 109.6 | C8—O1—H1O | 105.2 (16) |
C8—C7—H7B | 109.6 | S1—C21—H21A | 109.5 |
H7A—C7—H7B | 108.1 | S1—C21—H21B | 109.5 |
O1—C8—C9 | 107.10 (15) | H21A—C21—H21B | 109.5 |
O1—C8—C15 | 108.79 (14) | S1—C21—H21C | 109.5 |
C9—C8—C15 | 109.63 (14) | H21A—C21—H21C | 109.5 |
O1—C8—C7 | 108.67 (14) | H21B—C21—H21C | 109.5 |
C9—C8—C7 | 110.52 (14) | O3—S1—O4 | 114.04 (11) |
C15—C8—C7 | 111.98 (15) | O4—S1—O2 | 112.13 (11) |
C14—C9—C10 | 118.5 (2) | O3—S1—O2 | 112.41 (11) |
C14—C9—C8 | 121.67 (18) | O4—S1—C21 | 107.16 (17) |
C10—C9—C8 | 119.83 (17) | O3—S1—C21 | 105.84 (16) |
C11—C10—C9 | 121.0 (2) | O2—S1—C21 | 104.43 (17) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1WA···O3i | 0.85 (1) | 1.88 (1) | 2.732 (2) | 174 (3) |
O1W—H1WB···O4ii | 0.85 (1) | 1.89 (1) | 2.734 (2) | 174 (2) |
N1—H1N···O1W | 0.86 (1) | 1.87 (1) | 2.728 (2) | 176 (2) |
O1—H1O···O2 | 0.84 (1) | 1.92 (1) | 2.745 (2) | 168 (2) |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+2, −z+1. |