(R)-3-(tert-But­oxycarbon­yl)-5-methyl-1,2,3-oxa­thia­zolidine 2,2-dioxide

Laus, G.; Wurst, K.; Nerdinger, S.; Richter, F.; Schottenberger, H.

doi:10.1107/S2414314617008690

organic compounds

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ISSN: 2414-3146

Volume 2| Part 6| June 2017| x170869

https://doi.org/10.1107/S2414314617008690

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(R)-3-(tert-Butoxycarbonyl)-5-methyl-1,2,3-oxathiazolidine 2,2-dioxide

Gerhard Laus,^a ^* Klaus Wurst,^a Sven Nerdinger,^b Frank Richter ^b and Herwig Schottenberger ^a

^aUniversity of Innsbruck, Faculty of Chemistry and Pharmacy, Innrain 80, 6020 Innsbruck, Austria, and ^bSandoz GmbH, Biochemiestrasse 10, 6250 Kundl, Austria
^*Correspondence e-mail: gerhard.laus@uibk.ac.at

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 10 June 2017; accepted 11 June 2017; online 16 June 2017)

The chiral title compound, C₈H₁₅NO₅S, was obtained by cyclization of (R)-1-(tert-butoxycarbonylamino)-2-propanol with thionyl chloride and subsequent oxidation with sodium metaperiodate/ruthenium(IV) oxide. It crystallizes with two independent molecules in the asymmetric unit. In the crystal, C—H⋯O interactions link the molecules into a three-dimensional network.

Keywords: crystal structure; C—H⋯O contacts; oxathiazolidine; sulfamidate.

CCDC reference: 1555404

Structure description

Cyclic sulfamidates are valuable reactive intermediates, because ring-opening reactions proceed with total inversion at the stereogenic centre (Meléndez & Lubell, 2003 ). The title compound represents such a building block derived from (R)-1-amino-2-propanol useful for the preparation of substituted β-phenylethylamines, an important class of pharmacologically active compounds (Hebeisen et al., 2011 ). The configuration of the enantiomer has been assigned by reference to an unchanging chiral centre in the synthetic procedure and confirmed by anomalous-dispersion effects in diffraction measurements on the crystal: the Flack parameter was refined to 0.02 (2).

The title compound crystallizes with two independent molecules in the asymmetric unit. The five-membered rings adopt (O)C-envelope conformations, denoting the flap atoms, C1 and C6, are adjacent to the oxygen atoms. The methyl groups occupy equatorial positions (Fig. 1). The bonding geometries at the N atoms are close to planar, as the sums of the angles at N1 and N2 are 358.9 and 358.8°, respectively, and the N atoms lie only 0.092 and 0.094 Å out of the planes of the atoms to which they are bonded, as expected for an N-acyl fragment. In the crystal, C—H⋯O interactions (Table 1) are observed. The apolar tert-butyl groups and the polar sulfamidate rings are alternately arranged in layers parallel to the bc-plane (Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯O4ⁱ	0.99	2.40	3.360 (5)	164
C2—H2B⋯O9ⁱⁱ	0.99	2.52	3.200 (4)	126
C2—H2A⋯O8	0.99	2.52	3.205 (4)	126
C1—H1⋯O9ⁱⁱ	1.00	2.55	3.084 (4)	113
C8—H8A⋯O7ⁱⁱⁱ	0.98	2.57	3.547 (5)	174
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+1]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+2]$ ; (iii) $[-x+1, y+{\script{1\over 2}}, -z+1]$ .

Figure 1
The molecular structure of the two independent molecules in the asymmetric unit of the title compound, showing the atom labels and 50% probability displacement ellipsoids for non-H atoms.

Figure 2
Alternating layers of apolar and polar moieties parallel to the bc plane.

Related structures of N-substituted 1,2,3-oxathiazolidine 2,2-dioxides exhibit (O)C-envelope (Mata et al., 2012 ; Jiménez-Osés et al., 2009 ; Avenoza et al., 2004 ; Nicolaou et al., 2002 ), O-envelope (Son et al., 2016 ; Gritsonie et al., 1994 ), S-envelope (Achary et al., 2016 ), and (N)C-envelope (Carreras et al., 2007 ) conformations. These structures exhibited either close to planar (N-acyl-substituted, sum of angles >357°) or unequivocally pyramidal (N-alkyl-substituted, 335–345°) geometries at the N atoms.

Synthesis and crystallization

A solution of SOCl₂ (1.5 ml, 21 mmol) in CH₂Cl₂ (15 ml) was added to imidazole (4.7 g, 68 mmol) in CH₂Cl₂ (50 ml) at 0°C. After 90 min, (R)-1-(tert-butoxycarbonylamino)propan-2-ol (2.0 g, 11 mmol; Zhong et al., 1998 ) in CH₂Cl₂ (25 ml) was added, and the mixture was stirred for 2 h. The suspension was mixed with H₂O (90 ml) for 15 min. The organic phase was washed with citric acid (5.7 g) in H₂O (50 ml), then with a mixture of saturated brine (30 ml) and H₂O (30 ml). A solution of NaIO₄ (6.3 g, 30 mmol) in H₂O (60 ml) was added, then RuO₂^.H₂O (100 mg), and the mixture was well stirred for 4 h at room temperature. The organic phase was washed with a solution of Na ascorbate (1.7 g) in H₂O (15 ml), dried over MgSO₄ and concentrated under reduced pressure to yield 2.20 g (81%) of colourless product. Suitable crystals were obtained by slow evaporation of a solution in CH₂Cl₂/heptane, m.p. 107–108°C. ¹H NMR (300 MHz, CDCl₃): δ 1.51 (s, 9H), 1.55 (d, 3H), 3.62 (t, J = 9.8 Hz, 1H), 4.05 (dd, J = 5.6 and 9.9 Hz, 1H), 4.93 (m, 1H) p.p.m. ¹³C NMR (75 MHz, CDCl₃): δ 18.2, 28.1 (3 C), 51.8, 76.3, 85.4, 148.8 p.p.m. IR (neat): ν 2983, 1716, 1365, 1337, 1258, 1199, 1144, 1089, 1025, 921, 852, 825, 764, 730, 685, 598, 545 cm⁻¹.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₈H₁₅NO₅S
M_r	237.27
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	193
a, b, c (Å)	9.4093 (3), 10.5822 (4), 12.2844 (5)
β (°)	107.640 (1)
V (Å³)	1165.66 (7)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.28
Crystal size (mm)	0.06 × 0.05 × 0.02

Data collection
Diffractometer	Bruker D8 QUEST PHOTON 100
Absorption correction	Multi-scan (SADABS; Bruker, 2012 )
T_min, T_max	0.938, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	33847, 4342, 4094
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.073, 1.04
No. of reflections	4342
No. of parameters	272
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.28
Absolute structure	Flack x determined using 1855 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	0.02 (2)
Computer programs: APEX2 and SAINT (Bruker, 2012), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ) and Mercury (Macrae et al., 2008 ).

Structural data

CCDC reference: 1555404

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2414314617008690/hb4152sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617008690/hb4152Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617008690/hb4152Isup3.mol

Supporting information file. DOI: https://doi.org/10.1107/S2414314617008690/hb4152Isup4.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: Mercury (Macrae et al., 2008).

(R)-3-(tert-Butoxycarbonyl)-5-methyl-1,2,3-oxathiazolidine 2,2-dioxide top

Crystal data top

C₈H₁₅NO₅S	F(000) = 504
M_r = 237.27	D_x = 1.352 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 9.4093 (3) Å	Cell parameters from 9948 reflections
b = 10.5822 (4) Å	θ = 2.5–27.0°
c = 12.2844 (5) Å	µ = 0.28 mm⁻¹
β = 107.640 (1)°	T = 193 K
V = 1165.66 (7) Å³	Prism, colourless
Z = 4	0.06 × 0.05 × 0.02 mm

Data collection top

Bruker D8 QUEST PHOTON 100 diffractometer	4342 independent reflections
Radiation source: Incoatec Microfocus	4094 reflections with I > 2σ(I)
Multi layered optics monochromator	R_int = 0.030
Detector resolution: 10.4 pixels mm^-1	θ_max = 25.5°, θ_min = 2.3°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2012)	k = −12→12
T_min = 0.938, T_max = 0.971	l = −14→14
33847 measured reflections

Refinement top

Refinement on F²	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.0377P)² + 0.3902P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.027	(Δ/σ)_max < 0.001
wR(F²) = 0.073	Δρ_max = 0.23 e Å⁻³
S = 1.04	Δρ_min = −0.28 e Å⁻³
4342 reflections	Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
272 parameters	Extinction coefficient: 0.0255 (19)
1 restraint	Absolute structure: Flack x determined using 1855 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
Hydrogen site location: inferred from neighbouring sites	Absolute structure parameter: 0.02 (2)

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	U_iso*/U_eq
S1	0.62330 (9)	0.67259 (7)	0.85287 (6)	0.0250 (2)
S2	0.37651 (9)	0.33171 (7)	0.65306 (6)	0.0261 (2)
O1	0.6732 (2)	0.5996 (3)	0.96929 (18)	0.0319 (6)
O3	0.6538 (3)	0.5935 (3)	0.7696 (2)	0.0386 (7)
O2	0.6802 (3)	0.7969 (3)	0.8659 (2)	0.0408 (7)
O4	0.3738 (3)	0.7477 (3)	0.66348 (19)	0.0358 (7)
O5	0.2039 (2)	0.6996 (2)	0.75543 (17)	0.0284 (6)
O6	0.3235 (2)	0.3893 (3)	0.53039 (18)	0.0329 (6)
O7	0.3186 (3)	0.2066 (3)	0.6462 (2)	0.0396 (7)
O8	0.3483 (3)	0.4151 (3)	0.7343 (2)	0.0393 (7)
O9	0.6277 (3)	0.2530 (3)	0.83941 (19)	0.0395 (8)
O10	0.7964 (2)	0.3050 (2)	0.74775 (18)	0.0292 (6)
N1	0.4436 (3)	0.6742 (3)	0.8454 (2)	0.0239 (6)
N2	0.5553 (3)	0.3329 (3)	0.6599 (2)	0.0244 (6)
C1	0.5647 (3)	0.6155 (3)	1.0342 (2)	0.0274 (6)
H1	0.5791	0.6992	1.0737	0.033*
C2	0.4151 (3)	0.6111 (4)	0.9426 (2)	0.0270 (8)
H2A	0.3822	0.5228	0.9235	0.032*
H2B	0.3382	0.6566	0.9672	0.032*
C3	0.5916 (5)	0.5106 (4)	1.1197 (3)	0.0455 (11)
H3A	0.5215	0.5181	1.1643	0.068*
H3B	0.5768	0.4292	1.0798	0.068*
H3C	0.6940	0.5158	1.1709	0.068*
C4	0.3387 (4)	0.7112 (3)	0.7447 (3)	0.0240 (8)
C5	0.0685 (4)	0.7318 (4)	0.6575 (3)	0.0294 (8)
C6	0.4405 (3)	0.4745 (3)	0.5123 (2)	0.0288 (6)
H6	0.4428	0.5559	0.5540	0.035*
C7	0.5840 (4)	0.4009 (4)	0.5643 (3)	0.0269 (8)
H7A	0.6031	0.3412	0.5082	0.032*
H7B	0.6703	0.4585	0.5917	0.032*
C8	0.4016 (4)	0.4982 (4)	0.3859 (3)	0.0416 (10)
H8A	0.4764	0.5541	0.3707	0.062*
H8B	0.3999	0.4177	0.3460	0.062*
H8C	0.3032	0.5381	0.3587	0.062*
C9	0.6606 (4)	0.2940 (4)	0.7593 (3)	0.0258 (8)
C10	0.9306 (4)	0.2727 (4)	0.8444 (3)	0.0326 (8)
C51	0.0728 (5)	0.8705 (5)	0.6290 (5)	0.0585 (14)
H51A	0.0771	0.9213	0.6966	0.088*
H51B	0.1612	0.8876	0.6050	0.088*
H51C	−0.0172	0.8925	0.5670	0.088*
C52	0.0619 (5)	0.6479 (5)	0.5580 (3)	0.0579 (14)
H52A	−0.0265	0.6690	0.4942	0.087*
H52B	0.1517	0.6602	0.5346	0.087*
H52C	0.0560	0.5594	0.5799	0.087*
C53	−0.0562 (4)	0.7038 (6)	0.7066 (4)	0.0559 (13)
H53A	−0.0487	0.7602	0.7714	0.084*
H53B	−0.1521	0.7173	0.6479	0.084*
H53C	−0.0492	0.6158	0.7325	0.084*
C101	1.0564 (4)	0.3039 (6)	0.7948 (4)	0.0598 (15)
H10A	1.1525	0.2862	0.8519	0.090*
H10B	1.0462	0.2522	0.7268	0.090*
H10C	1.0514	0.3936	0.7740	0.090*
C102	0.9364 (5)	0.3583 (5)	0.9441 (3)	0.0579 (14)
H10D	1.0246	0.3377	1.0082	0.087*
H10E	0.9421	0.4465	0.9215	0.087*
H10F	0.8464	0.3461	0.9671	0.087*
C103	0.9308 (5)	0.1343 (4)	0.8720 (4)	0.0543 (13)
H10G	1.0197	0.1143	0.9357	0.081*
H10H	0.8412	0.1139	0.8934	0.081*
H10I	0.9316	0.0845	0.8049	0.081*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0159 (4)	0.0338 (5)	0.0254 (4)	−0.0013 (4)	0.0062 (3)	−0.0021 (4)
S2	0.0167 (5)	0.0339 (5)	0.0265 (4)	−0.0012 (4)	0.0050 (3)	−0.0003 (4)
O1	0.0210 (12)	0.0445 (14)	0.0290 (11)	0.0092 (11)	0.0060 (9)	0.0047 (11)
O3	0.0284 (15)	0.0559 (17)	0.0358 (14)	0.0003 (13)	0.0162 (11)	−0.0112 (13)
O2	0.0295 (15)	0.0399 (16)	0.0505 (15)	−0.0098 (13)	0.0087 (12)	0.0007 (12)
O4	0.0256 (17)	0.055 (2)	0.0282 (13)	0.0015 (12)	0.0094 (11)	0.0107 (12)
O5	0.0155 (11)	0.0435 (16)	0.0247 (11)	0.0038 (11)	0.0040 (9)	0.0058 (10)
O6	0.0218 (12)	0.0430 (14)	0.0294 (12)	0.0014 (11)	0.0012 (9)	0.0050 (11)
O7	0.0268 (15)	0.0384 (16)	0.0514 (15)	−0.0076 (12)	0.0086 (11)	0.0013 (11)
O8	0.0280 (15)	0.0544 (17)	0.0402 (15)	−0.0016 (13)	0.0174 (12)	−0.0110 (13)
O9	0.0258 (17)	0.062 (2)	0.0289 (13)	−0.0045 (12)	0.0063 (12)	0.0175 (13)
O10	0.0172 (12)	0.0428 (17)	0.0272 (11)	0.0052 (11)	0.0063 (9)	0.0069 (11)
N1	0.0174 (14)	0.0322 (15)	0.0227 (13)	0.0013 (14)	0.0069 (10)	0.0015 (14)
N2	0.0155 (14)	0.0369 (15)	0.0204 (12)	0.0000 (14)	0.0045 (10)	0.0029 (14)
C1	0.0276 (14)	0.0324 (15)	0.0223 (13)	0.0031 (12)	0.0076 (11)	−0.0003 (11)
C2	0.0224 (18)	0.039 (2)	0.0200 (15)	−0.0015 (16)	0.0067 (13)	−0.0010 (14)
C3	0.050 (2)	0.045 (3)	0.037 (2)	0.006 (2)	0.0065 (19)	0.0146 (18)
C4	0.0183 (19)	0.0286 (19)	0.0241 (16)	0.0001 (14)	0.0049 (14)	−0.0009 (13)
C5	0.0138 (18)	0.039 (2)	0.0302 (17)	0.0030 (17)	−0.0018 (14)	0.0033 (17)
C6	0.0261 (14)	0.0303 (14)	0.0281 (14)	0.0016 (11)	0.0056 (11)	0.0009 (12)
C7	0.0259 (18)	0.035 (2)	0.0209 (15)	0.0020 (16)	0.0093 (14)	0.0039 (13)
C8	0.043 (2)	0.049 (3)	0.0293 (19)	0.005 (2)	0.0053 (17)	0.0119 (17)
C9	0.0211 (19)	0.0319 (19)	0.0227 (16)	0.0003 (15)	0.0044 (14)	0.0017 (14)
C10	0.0201 (19)	0.040 (2)	0.0328 (18)	0.0056 (18)	0.0009 (15)	0.0080 (17)
C51	0.034 (2)	0.045 (3)	0.083 (3)	0.010 (2)	−0.002 (2)	0.019 (2)
C52	0.038 (2)	0.072 (4)	0.047 (2)	0.010 (2)	−0.0111 (18)	−0.019 (2)
C53	0.023 (2)	0.086 (4)	0.058 (2)	0.006 (2)	0.0109 (19)	0.016 (3)
C101	0.016 (2)	0.091 (4)	0.071 (3)	0.011 (2)	0.0110 (19)	0.034 (3)
C102	0.035 (2)	0.079 (4)	0.046 (2)	0.009 (3)	−0.0090 (18)	−0.019 (2)
C103	0.035 (2)	0.043 (3)	0.071 (3)	0.003 (2)	−0.006 (2)	0.015 (2)

Geometric parameters (Å, º) top

S1—O2	1.410 (3)	C5—C51	1.512 (6)
S1—O3	1.417 (3)	C6—C8	1.504 (4)
S1—O1	1.567 (2)	C6—C7	1.522 (4)
S1—N1	1.666 (3)	C6—H6	1.0000
S2—O8	1.416 (3)	C7—H7A	0.9900
S2—O7	1.425 (3)	C7—H7B	0.9900
S2—O6	1.561 (2)	C8—H8A	0.9800
S2—N2	1.659 (3)	C8—H8B	0.9800
O1—C1	1.483 (3)	C8—H8C	0.9800
O4—C4	1.206 (4)	C10—C103	1.504 (6)
O5—C4	1.320 (4)	C10—C102	1.510 (6)
O5—C5	1.502 (4)	C10—C101	1.522 (5)
O6—C6	1.491 (4)	C51—H51A	0.9800
O9—C9	1.199 (4)	C51—H51B	0.9800
O10—C9	1.333 (4)	C51—H51C	0.9800
O10—C10	1.487 (4)	C52—H52A	0.9800
N1—C4	1.385 (4)	C52—H52B	0.9800
N1—C2	1.461 (4)	C52—H52C	0.9800
N2—C9	1.382 (4)	C53—H53A	0.9800
N2—C7	1.470 (4)	C53—H53B	0.9800
C1—C3	1.496 (5)	C53—H53C	0.9800
C1—C2	1.513 (4)	C101—H10A	0.9800
C1—H1	1.0000	C101—H10B	0.9800
C2—H2A	0.9900	C101—H10C	0.9800
C2—H2B	0.9900	C102—H10D	0.9800
C3—H3A	0.9800	C102—H10E	0.9800
C3—H3B	0.9800	C102—H10F	0.9800
C3—H3C	0.9800	C103—H10G	0.9800
C5—C52	1.497 (5)	C103—H10H	0.9800
C5—C53	1.502 (5)	C103—H10I	0.9800

O2—S1—O3	118.69 (18)	N2—C7—H7A	111.1
O2—S1—O1	110.94 (16)	C6—C7—H7A	111.1
O3—S1—O1	107.29 (17)	N2—C7—H7B	111.1
O2—S1—N1	109.95 (16)	C6—C7—H7B	111.1
O3—S1—N1	112.98 (15)	H7A—C7—H7B	109.0
O1—S1—N1	94.22 (13)	C6—C8—H8A	109.5
O8—S2—O7	118.11 (18)	C6—C8—H8B	109.5
O8—S2—O6	111.31 (18)	H8A—C8—H8B	109.5
O7—S2—O6	107.53 (16)	C6—C8—H8C	109.5
O8—S2—N2	111.30 (16)	H8A—C8—H8C	109.5
O7—S2—N2	111.98 (16)	H8B—C8—H8C	109.5
O6—S2—N2	93.91 (13)	O9—C9—O10	127.8 (3)
C1—O1—S1	111.72 (18)	O9—C9—N2	122.6 (3)
C4—O5—C5	120.4 (2)	O10—C9—N2	109.5 (3)
C6—O6—S2	110.25 (17)	O10—C10—C103	110.3 (3)
C9—O10—C10	120.3 (3)	O10—C10—C102	108.8 (3)
C4—N1—C2	127.0 (3)	C103—C10—C102	113.8 (4)
C4—N1—S1	119.3 (2)	O10—C10—C101	101.9 (3)
C2—N1—S1	112.6 (2)	C103—C10—C101	110.7 (4)
C9—N2—C7	126.6 (3)	C102—C10—C101	110.6 (4)
C9—N2—S2	119.1 (2)	C5—C51—H51A	109.5
C7—N2—S2	113.1 (2)	C5—C51—H51B	109.5
O1—C1—C3	107.2 (3)	H51A—C51—H51B	109.5
O1—C1—C2	103.5 (2)	C5—C51—H51C	109.5
C3—C1—C2	114.9 (3)	H51A—C51—H51C	109.5
O1—C1—H1	110.3	H51B—C51—H51C	109.5
C3—C1—H1	110.3	C5—C52—H52A	109.5
C2—C1—H1	110.3	C5—C52—H52B	109.5
N1—C2—C1	103.6 (2)	H52A—C52—H52B	109.5
N1—C2—H2A	111.0	C5—C52—H52C	109.5
C1—C2—H2A	111.0	H52A—C52—H52C	109.5
N1—C2—H2B	111.0	H52B—C52—H52C	109.5
C1—C2—H2B	111.0	C5—C53—H53A	109.5
H2A—C2—H2B	109.0	C5—C53—H53B	109.5
C1—C3—H3A	109.5	H53A—C53—H53B	109.5
C1—C3—H3B	109.5	C5—C53—H53C	109.5
H3A—C3—H3B	109.5	H53A—C53—H53C	109.5
C1—C3—H3C	109.5	H53B—C53—H53C	109.5
H3A—C3—H3C	109.5	C10—C101—H10A	109.5
H3B—C3—H3C	109.5	C10—C101—H10B	109.5
O4—C4—O5	128.7 (3)	H10A—C101—H10B	109.5
O4—C4—N1	122.0 (3)	C10—C101—H10C	109.5
O5—C4—N1	109.3 (3)	H10A—C101—H10C	109.5
C52—C5—O5	109.6 (3)	H10B—C101—H10C	109.5
C52—C5—C53	111.5 (4)	C10—C102—H10D	109.5
O5—C5—C53	102.1 (3)	C10—C102—H10E	109.5
C52—C5—C51	112.6 (4)	H10D—C102—H10E	109.5
O5—C5—C51	109.3 (3)	C10—C102—H10F	109.5
C53—C5—C51	111.2 (4)	H10D—C102—H10F	109.5
O6—C6—C8	107.2 (2)	H10E—C102—H10F	109.5
O6—C6—C7	103.2 (3)	C10—C103—H10G	109.5
C8—C6—C7	115.2 (3)	C10—C103—H10H	109.5
O6—C6—H6	110.3	H10G—C103—H10H	109.5
C8—C6—H6	110.3	C10—C103—H10I	109.5
C7—C6—H6	110.3	H10G—C103—H10I	109.5
N2—C7—C6	103.4 (2)	H10H—C103—H10I	109.5

O2—S1—O1—C1	90.0 (2)	C5—O5—C4—O4	1.2 (6)
O3—S1—O1—C1	−138.9 (2)	C5—O5—C4—N1	−179.1 (3)
N1—S1—O1—C1	−23.2 (2)	C2—N1—C4—O4	−170.2 (4)
O8—S2—O6—C6	83.9 (2)	S1—N1—C4—O4	−3.3 (5)
O7—S2—O6—C6	−145.3 (2)	C2—N1—C4—O5	10.1 (5)
N2—S2—O6—C6	−30.8 (2)	S1—N1—C4—O5	176.9 (2)
O2—S1—N1—C4	76.9 (3)	C4—O5—C5—C52	61.1 (4)
O3—S1—N1—C4	−58.2 (3)	C4—O5—C5—C53	179.5 (3)
O1—S1—N1—C4	−169.0 (3)	C4—O5—C5—C51	−62.7 (4)
O2—S1—N1—C2	−114.4 (3)	S2—O6—C6—C8	165.0 (2)
O3—S1—N1—C2	110.5 (3)	S2—O6—C6—C7	43.0 (3)
O1—S1—N1—C2	−0.3 (3)	C9—N2—C7—C6	−152.5 (3)
O8—S2—N2—C9	62.5 (3)	S2—N2—C7—C6	14.8 (3)
O7—S2—N2—C9	−72.2 (3)	O6—C6—C7—N2	−33.4 (3)
O6—S2—N2—C9	177.2 (3)	C8—C6—C7—N2	−149.9 (3)
O8—S2—N2—C7	−105.9 (3)	C10—O10—C9—O9	−4.5 (6)
O7—S2—N2—C7	119.5 (3)	C10—O10—C9—N2	178.1 (3)
O6—S2—N2—C7	8.8 (3)	C7—N2—C9—O9	170.5 (4)
S1—O1—C1—C3	160.6 (2)	S2—N2—C9—O9	3.9 (5)
S1—O1—C1—C2	38.8 (3)	C7—N2—C9—O10	−11.9 (5)
C4—N1—C2—C1	−170.2 (3)	S2—N2—C9—O10	−178.6 (2)
S1—N1—C2—C1	22.2 (3)	C9—O10—C10—C103	64.5 (5)
O1—C1—C2—N1	−35.6 (3)	C9—O10—C10—C102	−61.0 (4)
C3—C1—C2—N1	−152.2 (3)	C9—O10—C10—C101	−177.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O4ⁱ	0.99	2.40	3.360 (5)	164
C2—H2B···O9ⁱⁱ	0.99	2.52	3.200 (4)	126
C2—H2A···O8	0.99	2.52	3.205 (4)	126
C1—H1···O9ⁱⁱ	1.00	2.55	3.084 (4)	113
C8—H8A···O7ⁱⁱⁱ	0.98	2.57	3.547 (5)	174

Symmetry codes: (i) −x+1, y−1/2, −z+1; (ii) −x+1, y+1/2, −z+2; (iii) −x+1, y+1/2, −z+1.

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