A crystallographic and thermal study of pridinol mesylate and its monohydrated solvate

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.

Computing details

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)

Crystal data

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) Å^3	Plate, colourless
Z = 4	0.50 × 0.30 × 0.20 mm

Data collection

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

Refinement on F^2	2 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.045	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.117	w = 1/[σ^2(Fo^2) + (0.0466P)^2 + 0.5916P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O2^i	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···O2^i	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)

Crystal data

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) Å^3	Plate, colourless
Z = 4	0.50 × 0.30 × 0.18 mm

Data collection

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

Refinement on F^2	5 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.051	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.133	w = 1/[σ^2(Fo^2) + (0.0509P)^2 + 0.6627P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O3^i	0.85 (1)	1.88 (1)	2.732 (2)	174 (3)
O1W—H1WB···O4^ii	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.