organic compounds
(R)-3-(tert-Butoxycarbonyl)-5-methyl-1,2,3-oxathiazolidine 2,2-dioxide
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
The chiral title compound, C8H15NO5S, was obtained by 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 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 was refined to 0.02 (2).
The title compound crystallizes with two independent molecules in the ). 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).
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. 1Related 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 .
details are summarized in Table 2
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Structural data
CCDC reference: 1555404
https://doi.org/10.1107/S2414314617008690/hb4152sup1.cif
contains datablocks I, global. DOI: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
Data collection: APEX2 (Bruker, 2012); cell
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).C8H15NO5S | F(000) = 504 |
Mr = 237.27 | Dx = 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 |
Bruker D8 QUEST PHOTON 100 diffractometer | 4342 independent reflections |
Radiation source: Incoatec Microfocus | 4094 reflections with I > 2σ(I) |
Multi layered optics monochromator | Rint = 0.030 |
Detector resolution: 10.4 pixels mm-1 | θmax = 25.5°, θmin = 2.3° |
φ and ω scans | h = −11→11 |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | k = −12→12 |
Tmin = 0.938, Tmax = 0.971 | l = −14→14 |
33847 measured reflections |
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0377P)2 + 0.3902P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.027 | (Δ/σ)max < 0.001 |
wR(F2) = 0.073 | Δρmax = 0.23 e Å−3 |
S = 1.04 | Δρmin = −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) |
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. |
x | y | z | Uiso*/Ueq | ||
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* |
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) |
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) |
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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