research communications
The crystal structures and Hirshfeld surface analyses of four 3,5-diacetyl-2-methyl-2,3-dihydro-1,3,4-thiadiazol-2-yl derivatives
aPG & Research Department of Physics, The New College (Autonomous), University of Madras, Chennai 600 014, Tamil Nadu, India, bDepartment of Biophysics, All India Institute of Medical Science, New Delhi 110 029, India, cCAS in Crystallography and Biophysics, University of Madras, Chennai 600 025, India, and dDepartment of Food Quality & Safety, Institute for Postharvest and Food Sciences, Volcani Center, ARO, Rishon LeZion 7528809, Israel
*Correspondence e-mail: mnizam.new@gmail.com
The title compounds, 4-(5-acetamido-3-acetyl-2-methyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)phenyl benzoate, C20H19N3O4S (I), 4-(5-acetamido-3-acetyl-2-methyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)phenyl isobutyrate 0.25-hydrate, C17H21N3O4S·0.25H2O (II), 4-(5-acetamido-3-acetyl-2-methyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)phenyl propionate, C16H19N3O4S (III) and 4-(5-acetamido-3-acetyl-2-methyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)phenyl cinnamate chloroform hemisolvate, C22H21N3O4S·0.5CHCl3 (IV), all crystallize with two independent molecules (A and B) in the in the triclinic P Compound II crystallizes as a quaterhydrate, while compound IV crystallizes as a chloroform hemisolvate. In compounds I, II, III (molecules A and B) and IV (molecule A) the five-membered thiadiazole ring adopts an with the tetrasubstituted C atom as the flap. In molecule B of IV this ring is flat (r.m.s. deviation 0.044 Å). The central benzene ring is in general almost normal to the mean plane of the thiadiazole ring in each molecule, with dihedral angles ranging from 75.8 (1) to 85.5 (2)°. In the crystals of all four compounds, the A and B molecules are linked via strong N—H⋯O hydrogen bonds and generate centrosymmetric four-membered R44(28) ring motifs. There are C—H⋯O hydrogen bonds present in the crystals of all four compounds, and in I and II there are also C—H⋯π interactions present. The intermolecular contacts in the crystals of all four compounds were analysed using Hirshfeld surface analysis and two-dimensional fingerprint plots.
1. Chemical context
Nitrogen-containing et al., 2013; Huq et al., 2010, Rajkumar et al., 2014, 2015; Thirunavukkarsu et al., 2017; Babu et al., 2014a,b) activities. Suitably substituted 1,3,4-thiadiazoles that incorporate the toxiphoric —N=C—S– linkage have attracted great attention owing to their broad spectrum of biological activities, including anti-inflammatory (Udupi et al., 2000), herbicidal antimicrobial, bactericidal (Tehranchian et al., 2005), antiviral and anti-HIV-1 (Invidiata et al., 1996) properties. Their action depends on the type and location of the polar substituents on the heterocyclic ring. In general, the pharmacological effect of potential drugs depends on the stereochemistry and ring conformations. The amide linkage [–NHC(O)–] is known to be strong enough to form and maintain protein architectures and has been utilized to create various molecular devices for a range of purposes in organic chemistry. Depending on the types of substitution at the α, β and keto C atoms, and the conformational flexibility of the substituent groups, a variety of ss-acetamido offering the possibility of intermolecular interactions can be obtained. Recognizing the importance of such compounds in drug discovery and as part of our ongoing investigation of acetamide derivatives, the promising biological potency of 1,3,4-thiadiazoles and variously substituted 1,3,4-thiadiazole frameworks, the title compounds have been prepared and their crystal structures are reported on herein.
are one of the most important classes of biologically active compounds, exhibiting antimicrobial, antitumour and anti–inflammatory (Sethuram2. Structural commentary
The molecular structures and conformations of the two crystallographically independent molecules (A and B), of compounds I, II, III and IV are illustrated in Figs. 1, 2, 3 and 4, respectively. In all four compounds, the bond lengths and angles in the two independent molecules agree with each other. The normal probability plot analyses (International Tables for X-ray Crystallography, 1974, Vol. IV, pp. 293–309) for both bond lengths and bond angles show that the differences between the two independent molecules are of a statistical nature. The geometric parameters (bond lengths and bond angles) are very similar to those observed in previously reported structures (Aridoss et al., 2008).
The dihedral angle between mean plane of the thiadiazole ring [(S1/N1/N2/C3/C6) in I and II, (S1/N2/N3/C3/C6) in III and (S1/N1/N3/C3/C6) in IV] and the acetamide side chain (N3/C4/O2/C5) are 17.2 (2) and 17.3 (2)°, for compound I (molecules A and B, respectively). In compounds II, III and IV the corresponding dihedral angles are 11.2 (2) and 19.6 (2)°, 61.4 (1) and 13.4 (1)° and 15.9 (1) and 6.1 (1)°, respectively. The dihedral angle between the mean plane of the thiadiazole ring and the phenyl ring (C8–C13) are respectively, 88.5 (2) and 82.8 (2)°, for molecules A and B of compound I, and 87.8 (2) and 77.0 (1)°, respectively, for compound II. The corresponding dihedral angles for molecules A and B are 77.2 (1) and 75.8 (1) ° in III, and 79.9 (1) and 87.0 (1)° in IV. The dihedral angle between phenyl ring (C8–C13) and the acetamide side chain (N3/C4/O2/C5) are 86.9 (2) and 80.2 (2)°, for compound I (molecules A and B, respectively). In compound II, for molecules A and B, the corresponding angles are 84.2 (2) and 81.6 (2)°, respectively.
In molecules A and B of compounds I, II, III and molecule B of compound IV, the thiadiazole rings (S1/C3/N2/N3/C6) adopt envelope conformations, with atom C6 deviating from the mean plane of the remaining four atoms: by 0.132 (3) and 0.110 (3) Å, for atoms C6A and C6B, respectively, for I, 0.132 (2) and 0.136 (2) Å for II, 0.395 (3) and 0.350 (3) Å for III and 0.321 (3) Å for molecule B of IV. In molecule B of compound IV, this ring is planar (r.m.s. deviation 0.044 Å).
In three of the compounds there is a certain disorder; in compound I the phenyl benzoate group is disordered, in compound II the methyl propanoate group is disordered, and in compound III the O atom of the ester group is disordered. The geometries were regularized using soft restraints; see §7, Refinement.
3. Supramolecular features
In all compounds, the crystal packing is stabilized by strong N—H⋯O intermolecular hydrogen bonds (see Tables 1, 2, 3 and 4, and Figs. 5, 6, 7 and 8).
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In the crystals of all four compounds, the A and B molecules are linked via strong N—H⋯O hydrogen bonds and generate centrosymmetric four-membered R44(28) ring motifs. There are C—H⋯O hydrogen bonds present in the crystals of all four compounds. For I they link the rings to form layers parallel to the ab plane, while for II they link the rings, that stack up the a axis, to form columns. For III, neighbouring rings are linked by C—H⋯O hydrogen bonds to form ribbons propagating along the b-axis direction. Finally, for IV, the rings that stack up the b-axis are linked by C—H⋯O hydrogen bonds to form columns, which are linked by a further C—H⋯O hydrogen bond to form a supramolecular three-dimensional structure.
In the crystals of I and II, there are also C—H⋯π interactions present. In the former they link the layers, while in the latter they link the columns, to form supramolecular three-dimensional structures.
4. Hirshfeld surface analysis
A recent article by Tiekink and collaborators (Tan et al., 2019) reviews and describes the uses and utility of Hirshfeld surface analysis (Spackman & Jayatilaka, 2009), and the associated two-dimensional fingerprint plots (McKinnon et al., 2007), to analyse intermolecular contacts in crystals. The various calculations were performed with CrystalExplorer17 (Turner et al., 2017).
The Hirshfeld surfaces of compounds I–IV mapped over dnorm are given in Fig. 9, and the intermolecular contacts are illustrated in Fig. 10 for I, Fig. 11 for II, Fig. 12 for III and Fig. 13 for IV. They are colour-mapped with the normalized contact distance, dnorm, ranging from red (distances shorter than the sum of the van der Waals radii) through white to blue (distances longer than the sum of the van der Waals radii). The dnorm surface was mapped over a fixed colour scale of −0.763 (red) to 1.539 (blue) for compound I, −0.593 (red) to 1.357 (blue) for compound II, −0.593 (red) to 1.607 (blue) for compound III and −0.617 (red) to 2.422 (blue) for compound IV, where the red spots indicate the intermolecular contacts involved in the hydrogen bonding.
The fingerprint plots are given in Figs. 14, 15, 16 and 17, revealing similar trends for the principal intermolecular contacts. For compound I, they reveal that the principal intermolecular contacts are H⋯H at 42.5% (Fig. 14b), O⋯H/H⋯O at 24.2% (Fig. 14c), C⋯H/H⋯C contacts at 21.3% (Fig. 14d) and N⋯H/H⋯N at 5.2% (Fig. 14e), followed by the S⋯H/H⋯S at 4.1% (Fig. 14f). For compound II, the principal intermolecular contacts are H⋯H at 50.0% (Fig. 15b), O⋯H/H⋯O at 23.3% (Fig. 15c), C⋯H/H⋯C contacts at 14.2% (Fig. 15d) and N⋯H/H⋯N at 5.3% (Fig. 15e) followed by the S⋯H/H⋯S at 4.4% (Fig. 15f). For compound III, the principal intermolecular contacts are H⋯H at 51.0% (Fig. 16b), O⋯H/H⋯O at 26.4% (Fig. 16c), C⋯H/H⋯C contacts at 8.3% (Fig. 16d) and S⋯H/H⋯S at 4.4% (Fig. 15e) followed by the N⋯H/H⋯N at 4.1% (Fig. 15f) and C⋯ C contacts at 1.5%. For compound IV, the principal intermolecular contacts are H⋯H at 35.3% (Fig. 17b), O⋯H/H⋯O at 20.0% (Fig. 17c), Cl⋯H/H⋯Cl at 15.7% (Fig. 17d), C⋯H/H⋯C at 13.7% (Fig. 17e), S⋯H/H⋯S at 3.3% (Fig. 17f), N⋯H/H⋯N at 3.3% (Fig. 17c) followed by the C⋯C contacts at 1.6% (Fig. 17h). In all compounds, the H⋯H intermolecular contacts predominate, followed by the O⋯H/H⋯O contacts.
5. Database survey
A search of the Cambridge Structural Database (Version 5.40, last update May 2019; Groom et al., 2016) for (5-acetamido-3-acetyl-2-methyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)phenyl revealed the presence of three relevant compounds, viz. N-(4-acetyl-5-(4-fluorophenyl)-4,5-dihydro-1,3,4-thiadiazol-2-yl) acetamide (CSD refcode IDOFOY; Kavitha et al., 2013), N-(4-acetyl-5-(3-methoxyphenyl)-4,5-dihydro-1,3,4-thiadiazol-2-yl) acetamide (IGAREO; Aridoss et al., 2008), that crystallized in P21 with two independent molecules in the and 2-acetylamino-4-acetyl-5-phenyl-Δ2-1,3,4-thiadiazoline (YOLKAL; Usova et al., 1994). Here, the mean plane of the thiadiazole ring is almost normal to the 5-phenyl ring with dihedral angles of ca 86.82, 88.50 (68.46) and 84.06°, respectively. This situation is very similar to that in the title compounds where this dihedral angle varies from 75.8 (1) to 85.5 (2)°.
6. Synthesis and crystallization
Synthesis of 4-(3,5-diacetyl-2-methyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)phenyl benzoate (I) To a clean and dry 250 ml two-neck round-bottom flask fitted with condenser and addition funnel containing 4-hydroxy acetophenone (0.5 mol) was added chloroform (200 ml) under continuous stirring and the reaction mixture was cooled to 288–293 K. Benzoyl chloride (0.5 mol) was added dropwise and stirring continued for a further 15 min and then potassium carbonate (0.5 mol) was slowly added. The reaction continued for another 4 h, monitored using TLC. The reaction mass was transferred into a 1 l beaker and washed twice with water (2 × 250 ml). The chloroform layer was separated and washed with a 10% NaOH solution (2 × 250 ml) and dried with anhydrous sodium sulfate followed by concentration under reduced pressure using rotary vacuum before being cooled and hexane added. Thiosemicarbazide (0.1 mol) dissolved in 20 ml of 1 N hydrochloric acid was added slowly under stirring to 4-acetylphenyl benzoate (0.1 mol) dissolved in 50 ml of ethanol. After the addition of thiosemicarbazide, 4-[(1-(2-carbamothioylhydrazinylidene)ethyl]phenyl benzoate (in solid form) was formed within 4 min. The precipitate was filtered and washed with water, followed by hexane. 4-[(1-(2-Carbamothioylhydrazinylidene)ethyl]phenyl benzoate (0.5 mol) was dissolved in 10 ml of acetic anhydride and the mixture heated at 383 K for 3 h with magnetic stirring. The reaction was monitored using TLC, and once complete the reaction mass was quenched in crushed ice with stirring. The solid product obtained was filtered, washed with cold water followed by hexane and then air-dried. Recrystallization using chloroform yielded colourless block-like crystals of compound I.
Synthesis of 4-(3,5-diacetyl-2-methyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)phenyl isobutyrate (II) To a clean and dry 250 ml two-neck round-bottom flask fitted with condenser and addition funnel containing 4-hydroxy acetophenone (0.5 mol) was added chloroform (200 ml) under continuous stirring and the reaction mixture was cooled to 288–293 K. Isobutyryl chloride (0.5 mol) was added dropwise and stirring continued for a further 15 min and then potassium carbonate (0.5 mol) was slowly added. The reaction continued for another 4 h, monitored using TLC. The reaction mass was then transferred into a 1 l beaker and washed twice with water (2 × 250 ml). The chloroform layer was separated and washed with a 10% NaOH solution (2 × 250 ml) and dried with anhydrous sodium sulfate then concentrated under reduced pressure using a rotary vacuum, cooled and hexane was added. Thiosemicarbazide (0.91 g, 0.01 mol) was added to a 50 ml ethanolic solution of 4-acetylphenyl isobutyrate (0.01 mol) under continuous stirring. The resulting mixture refluxed at 333 K and the purity of the products as well as the composition of the reaction was monitored by TLC using ethyl acetate: hexane (3:7). The reaction mixture was cooled to room temperature and the separated product was filtered. 4-[(1-(2-Carbamothioylhydrazinylidene)ethyl]phenyl 2-methylpropanoate (0.5 mol) was dissolved in 10 ml of acetic anhydride and the mixture was heated at 383 K for 3 h under magnetic stirring. The reaction was monitored using TLC, and once complete the reaction mass was quenched in crushed ice cubes with stirring. The solid product obtained was filtered, washed with cold water followed by hexane and then air-dried. Recrystallization using chloroform yielded colourless block-like crystals of compound II.
Synthesis of 4-(3,5-diacetyl-2-methyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)phenyl propionate (III) To a clean and dry 250 ml two-neck round-bottom flask fitted with condenser and addition funnel containing 4-hydroxy acetophenone (0.5 mol) was added chloroform (200 ml) under continuous stirring and the reaction mixture was cooled to 288–293 K. Propanoyl chloride (0.5 mol) was then added dropwise. Stirring continued for another 15 min and then potassium carbonate (0.5 mol) was slowly added. The reaction was continued for another 4 h and monitored using TLC. The reaction mass was transferred into a 1 l beaker and washed twice with water (2 × 250 ml). The chloroform layer was separated and washed with a 10% NaOH solution (2 × 250 ml) and dried with anhydrous sodium sulfate followed by concentration under reduced pressure using a rotary vacuum, cooled and hexane was added to it. Thiosemicarbazide (0.91g, 0.01 mol) was added to 50 ml of an ethanolic solution of 4-acetylphenyl propionate (0.01 mol) under continuous stirring. The resulting mixture was refluxed at 333 K and the purity of the products as well as composition of the reaction was monitored by TLC using ethyl acetate:hexane (3:7). The reaction mixture was cooled to room temperature and the separated product was filtered. 4-[(1-(2 Carbamothioyl hydrazinylidene)ethyl]phenyl propanoate (0.5 mol) was dissolved in 10 ml of acetic anhydride and the mixture was heated at 383 K for 3 h under magnetic stirring. The reaction was monitored using TLC, and once complete the mass was quenched in crushed ice under stirring. The solid product obtained was filtered, washed with cold water followed by hexane and then air-dried. Recrystallization using chloroform yielded colourless block-like crystals of compound III.
Synthesis of 4-(3,5-diacetyl-2-methyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)phenyl cinnamate (IV) To a clean and dry 250 ml two-neck round-bottom flask fitted with condenser and addition funnel containing 4-hydroxy acetophenone (0.5 mol) was added chloroform (200 ml) under continuous stirring and the reaction mixture was cooled to 288–293 K. Cinnamoyl chloride (0.5 mol) was then added dropwise. Stirring continued for another 15 min and potassium carbonate (0.5 mol) was slowly added. The reaction continued for another 4 h and was monitored using TLC. The reaction mass was transferred into a 1 l beaker and washed twice with water (2 × 250 ml). The chloroform layer separated and was washed with a 10% NaOH solution (2 × 250 ml) and dried with anhydrous sodium sulfate followed by concentration under reduced pressure using a rotary vacuum, cooled and hexane added. Thiosemicarbazide (0.1 mol) dissolved in 20 ml of 1 N hydrochloric acid was added slowly under stirring to 4-acetylphenyl cinnamate (0.1 mol) dissolved in 50 ml of ethanol. After the addition of thiosemicarbazide, 4-[(1-(2-carbamothioylhydrazinylidene)ethyl]phenyl benzoate (in solid form) was formed within 4 min. The precipitate was filtered off and washed with water, followed by hexane. 4-[(1-(2-Carbamothioylhydrazinylidene)ethyl]phenyl-3-phenylprop-2-enoate (0.5 mol) was dissolved in 10 ml of acetic anhydride and the mixture was heated at 383 K for 3 h under magnetic stirring. The reaction was monitored using TLC, and once complete the reaction mass was quenched in crushed ice under stirring. The solid product obtained was filtered, washed with cold water followed by hexane and then air-dried. Recrystallization using chloroform yielded colourless block-like crystals of compound IV.
7. Refinement
Crystal data, data collection and structure . For compounds I and II, the NH H atoms were located in difference-Fourier maps and freely refined. For compounds III and IV they were included in calculated positions and refined as riding: N—H = 0.93 Å with Uiso(H) = 1.2Ueq(N). All C-bound H atoms were positioned geometrically and constrained to ride on their parent atoms: C—H = 0.93–0.98 Å with Uiso(H) = 1.5Ueq(C-methyl) and 1.2Ueq(C) for other H atoms. In compound I, the phenyl benzoate group is disordered [occupancy ratios of 0.553 (5): 0.447 (5) and 0.661 (6):0.339 (6) in molecules A and B, respectively]. In compound II, the methyl propanoate group in molecule B is disordered [occupancy ratio 0.723 (5):0.277 (5)]. In compound III, the O atom of the ester group of molecule B is disordered [occupancy ratio of 0.68 (6):0.32 (6)]. The geometries were regularized using soft restraints.
details are summarized in Table 5
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Supporting information
https://doi.org/10.1107/S2056989019011915/su5508sup1.cif
contains datablocks global, I, II, III, IV. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989019011915/su5508Isup5.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989019011915/su5508Isup5.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989019011915/su5508IIsup6.cml
Structure factors: contains datablock III. DOI: https://doi.org/10.1107/S2056989019011915/su5508IIIsup7.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989019011915/su5508IIIsup7.cml
Structure factors: contains datablock IV. DOI: https://doi.org/10.1107/S2056989019011915/su5508IVsup8.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989019011915/su5508IVsup8.cml
For all structures, data collection: APEX2 (Bruker, 2008). Cell
APEX2 (Bruker, 2008) for (I), (II); SAINT (Bruker, 2008) for (III), (IV). For all structures, data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS2018/3 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012), publCIF (Westrip, 2010) and PLATON (Spek, 2009).C20H19N3O4S | Z = 4 |
Mr = 397.44 | F(000) = 832 |
Triclinic, P1 | Dx = 1.310 Mg m−3 |
a = 6.7559 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 16.9258 (2) Å | Cell parameters from 7061 reflections |
c = 19.0611 (3) Å | θ = 1.2–25.0° |
α = 110.447 (1)° | µ = 0.19 mm−1 |
β = 96.854 (2)° | T = 293 K |
γ = 93.370 (1)° | Block, colourless |
V = 2015.84 (5) Å3 | 0.30 × 0.25 × 0.20 mm |
Bruker Kappa APEXII CCD diffractometer | 4821 reflections with I > 2σ(I) |
ω and φ scans | Rint = 0.029 |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | θmax = 25.0°, θmin = 1.2° |
Tmin = 0.648, Tmax = 0.763 | h = −8→8 |
27547 measured reflections | k = −17→20 |
7061 independent reflections | l = −22→22 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.060 | Hydrogen site location: mixed |
wR(F2) = 0.226 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.83 | w = 1/[σ2(Fo2) + (0.173P)2 + 1.4455P] where P = (Fo2 + 2Fc2)/3 |
7061 reflections | (Δ/σ)max < 0.001 |
635 parameters | Δρmax = 0.38 e Å−3 |
523 restraints | Δρmin = −0.56 e Å−3 |
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 | Occ. (<1) | |
C1A | 0.2219 (6) | 0.4068 (2) | 0.0385 (2) | 0.0656 (9) | |
H1A1 | 0.177958 | 0.462086 | 0.058777 | 0.098* | |
H1A2 | 0.184605 | 0.384459 | −0.015565 | 0.098* | |
H1A3 | 0.364971 | 0.410730 | 0.050786 | 0.098* | |
C2A | 0.1252 (5) | 0.34900 (19) | 0.07183 (18) | 0.0543 (8) | |
C6A | 0.0955 (5) | 0.20448 (19) | 0.08168 (18) | 0.0520 (7) | |
C3A | 0.3164 (4) | 0.16342 (18) | −0.02111 (17) | 0.0491 (7) | |
C4A | 0.4572 (5) | 0.0414 (2) | −0.10248 (19) | 0.0609 (9) | |
C5A | 0.6199 (7) | 0.0180 (2) | −0.1495 (2) | 0.0814 (11) | |
H5A1 | 0.746604 | 0.029517 | −0.117187 | 0.122* | |
H5A2 | 0.621092 | 0.050733 | −0.181743 | 0.122* | |
H5A3 | 0.597016 | −0.041245 | −0.180053 | 0.122* | |
C7A | −0.1299 (5) | 0.1951 (2) | 0.0779 (2) | 0.0701 (10) | |
H7A1 | −0.169166 | 0.243320 | 0.116042 | 0.105* | |
H7A2 | −0.171080 | 0.144398 | 0.086486 | 0.105* | |
H7A3 | −0.192434 | 0.191664 | 0.028849 | 0.105* | |
C8A | 0.2146 (5) | 0.22651 (19) | 0.16091 (18) | 0.0541 (8) | |
C9A | 0.4050 (5) | 0.2035 (2) | 0.1704 (2) | 0.0637 (9) | |
H9A | 0.458678 | 0.170827 | 0.128259 | 0.076* | |
C10A | 0.5187 (7) | 0.2281 (3) | 0.2417 (3) | 0.0815 (12) | |
H10A | 0.646125 | 0.211083 | 0.247511 | 0.098* | |
C11A | 0.4406 (9) | 0.2779 (3) | 0.3036 (2) | 0.0942 (15) | |
C12A | 0.2516 (9) | 0.3016 (3) | 0.2952 (3) | 0.1005 (15) | |
H12A | 0.198292 | 0.334662 | 0.337239 | 0.121* | |
C13A | 0.1417 (7) | 0.2764 (3) | 0.2247 (2) | 0.0800 (11) | |
H13A | 0.014074 | 0.293392 | 0.219469 | 0.096* | |
C5B | −0.3939 (6) | 0.4189 (2) | 0.1997 (3) | 0.0781 (11) | |
H5B1 | −0.316132 | 0.410587 | 0.241635 | 0.117* | |
H5B2 | −0.362202 | 0.379959 | 0.153106 | 0.117* | |
H5B3 | −0.534022 | 0.409008 | 0.201844 | 0.117* | |
C4B | −0.3463 (5) | 0.5073 (2) | 0.2036 (2) | 0.0600 (8) | |
C3B | −0.1030 (5) | 0.60085 (19) | 0.17747 (17) | 0.0491 (7) | |
C6B | 0.0218 (5) | 0.75618 (19) | 0.21718 (18) | 0.0544 (8) | |
C7B | −0.0680 (6) | 0.8261 (2) | 0.1948 (2) | 0.0736 (10) | |
H7B1 | 0.037946 | 0.865664 | 0.193445 | 0.110* | |
H7B2 | −0.150634 | 0.855154 | 0.231292 | 0.110* | |
H7B3 | −0.147948 | 0.801636 | 0.145728 | 0.110* | |
C8B | 0.1840 (5) | 0.78728 (19) | 0.28650 (17) | 0.0544 (8) | |
C13B | 0.2002 (7) | 0.8682 (3) | 0.3381 (2) | 0.0900 (14) | |
H13B | 0.116198 | 0.906477 | 0.329469 | 0.108* | |
C12B | 0.3399 (9) | 0.8936 (3) | 0.4029 (3) | 0.119 (2) | |
H12B | 0.347492 | 0.948328 | 0.438345 | 0.143* | |
C11B | 0.4662 (7) | 0.8387 (3) | 0.4147 (2) | 0.0940 (14) | |
C10B | 0.4553 (6) | 0.7583 (3) | 0.3638 (2) | 0.0811 (11) | |
H10B | 0.541883 | 0.720683 | 0.372222 | 0.097* | |
C9B | 0.3147 (6) | 0.7332 (2) | 0.2996 (2) | 0.0699 (10) | |
H9B | 0.308075 | 0.678469 | 0.264329 | 0.084* | |
C2B | 0.2436 (5) | 0.7107 (2) | 0.11765 (19) | 0.0609 (8) | |
C1B | 0.3273 (6) | 0.6394 (2) | 0.0626 (2) | 0.0734 (10) | |
H1B1 | 0.415555 | 0.661491 | 0.036299 | 0.110* | |
H1B2 | 0.219721 | 0.601912 | 0.026726 | 0.110* | |
H1B3 | 0.400488 | 0.608835 | 0.089090 | 0.110* | |
N1A | 0.1674 (4) | 0.26824 (15) | 0.04924 (14) | 0.0506 (6) | |
N2A | 0.3109 (4) | 0.24387 (15) | 0.00068 (14) | 0.0499 (6) | |
N3A | 0.4450 (4) | 0.12653 (16) | −0.07072 (15) | 0.0528 (6) | |
H3A | 0.515 (5) | 0.152 (2) | −0.0914 (18) | 0.051 (9)* | |
N1B | 0.0966 (4) | 0.69192 (15) | 0.15279 (14) | 0.0532 (6) | |
N2B | 0.0369 (4) | 0.60619 (15) | 0.13948 (14) | 0.0529 (6) | |
N3B | −0.1812 (4) | 0.52161 (17) | 0.17374 (16) | 0.0549 (7) | |
H3B | −0.117 (6) | 0.482 (3) | 0.151 (2) | 0.080 (13)* | |
O1A | 0.0081 (4) | 0.37406 (15) | 0.11807 (15) | 0.0726 (7) | |
O2A | 0.3441 (5) | −0.00950 (15) | −0.09099 (17) | 0.0862 (8) | |
O1B | 0.3065 (4) | 0.78560 (15) | 0.13218 (16) | 0.0791 (8) | |
O2B | −0.4457 (4) | 0.56429 (18) | 0.23256 (19) | 0.0913 (9) | |
S1A | 0.15994 (13) | 0.10508 (5) | 0.01356 (5) | 0.0586 (3) | |
S1B | −0.18822 (13) | 0.69320 (5) | 0.23393 (6) | 0.0656 (3) | |
C14A | 0.697 (2) | 0.3397 (10) | 0.4045 (6) | 0.121 (3) | 0.553 (5) |
C15A | 0.7452 (13) | 0.3657 (5) | 0.4903 (3) | 0.113 (3) | 0.553 (5) |
C16A | 0.9402 (12) | 0.3664 (6) | 0.5236 (5) | 0.175 (4) | 0.553 (5) |
H16A | 1.032983 | 0.338544 | 0.494131 | 0.210* | 0.553 (5) |
C17A | 0.9967 (13) | 0.4088 (7) | 0.6011 (5) | 0.181 (5) | 0.553 (5) |
H17A | 1.127142 | 0.409308 | 0.623366 | 0.217* | 0.553 (5) |
C18A | 0.8581 (17) | 0.4505 (6) | 0.6452 (3) | 0.172 (5) | 0.553 (5) |
H18A | 0.895807 | 0.478825 | 0.696988 | 0.207* | 0.553 (5) |
C19A | 0.6630 (15) | 0.4497 (6) | 0.6119 (4) | 0.155 (4) | 0.553 (5) |
H19A | 0.570311 | 0.477579 | 0.641375 | 0.185* | 0.553 (5) |
C20A | 0.6066 (11) | 0.4073 (5) | 0.5344 (4) | 0.138 (4) | 0.553 (5) |
H20A | 0.476148 | 0.406815 | 0.512140 | 0.165* | 0.553 (5) |
O3A | 0.5068 (13) | 0.3112 (7) | 0.3822 (5) | 0.102 (3) | 0.553 (5) |
O4A | 0.754 (3) | 0.3795 (13) | 0.3656 (12) | 0.280 (10) | 0.553 (5) |
C14C | 0.799 (2) | 0.3142 (11) | 0.3741 (8) | 0.121 (4) | 0.447 (5) |
C15C | 0.8754 (14) | 0.3580 (5) | 0.4579 (4) | 0.120 (3) | 0.447 (5) |
C16C | 0.8530 (11) | 0.3003 (5) | 0.4941 (4) | 0.091 (3) | 0.447 (5) |
H16C | 0.754803 | 0.254222 | 0.473476 | 0.110* | 0.447 (5) |
C17C | 0.9775 (14) | 0.3113 (6) | 0.5611 (4) | 0.117 (4) | 0.447 (5) |
H17C | 0.962484 | 0.272708 | 0.585356 | 0.141* | 0.447 (5) |
C18C | 1.1243 (15) | 0.3801 (7) | 0.5920 (4) | 0.157 (5) | 0.447 (5) |
H18C | 1.207516 | 0.387540 | 0.636820 | 0.189* | 0.447 (5) |
C19C | 1.1466 (16) | 0.4379 (6) | 0.5558 (6) | 0.176 (5) | 0.447 (5) |
H19C | 1.244869 | 0.483887 | 0.576403 | 0.212* | 0.447 (5) |
C20C | 1.0222 (17) | 0.4268 (6) | 0.4887 (5) | 0.162 (5) | 0.447 (5) |
H20C | 1.037190 | 0.465403 | 0.464522 | 0.194* | 0.447 (5) |
O3C | 0.5988 (14) | 0.2887 (7) | 0.3676 (6) | 0.088 (3) | 0.447 (5) |
O4C | 0.825 (2) | 0.3587 (10) | 0.3401 (9) | 0.173 (6) | 0.447 (5) |
C14B | 0.7656 (13) | 0.8772 (6) | 0.4908 (5) | 0.083 (2) | 0.661 (6) |
C15B | 0.8793 (11) | 0.8962 (5) | 0.5669 (3) | 0.073 (2) | 0.661 (6) |
C16B | 0.7909 (7) | 0.8815 (4) | 0.6240 (5) | 0.085 (2) | 0.661 (6) |
H16B | 0.656588 | 0.860085 | 0.614983 | 0.103* | 0.661 (6) |
C17B | 0.9034 (15) | 0.8987 (4) | 0.6947 (4) | 0.095 (2) | 0.661 (6) |
H17B | 0.844281 | 0.888860 | 0.732942 | 0.114* | 0.661 (6) |
C18B | 1.1042 (14) | 0.9306 (5) | 0.7082 (3) | 0.092 (3) | 0.661 (6) |
H18B | 1.179435 | 0.942175 | 0.755513 | 0.110* | 0.661 (6) |
C19B | 1.1925 (6) | 0.9453 (6) | 0.6511 (5) | 0.120 (3) | 0.661 (6) |
H19B | 1.326900 | 0.966716 | 0.660124 | 0.144* | 0.661 (6) |
C20B | 1.0801 (13) | 0.9281 (6) | 0.5804 (4) | 0.110 (3) | 0.661 (6) |
H20B | 1.139211 | 0.937942 | 0.542164 | 0.132* | 0.661 (6) |
O3B | 0.5721 (8) | 0.8573 (4) | 0.4871 (3) | 0.0906 (17) | 0.661 (6) |
O4B | 0.8318 (9) | 0.8830 (5) | 0.4386 (3) | 0.149 (3) | 0.661 (6) |
C14D | 0.6548 (19) | 0.8629 (9) | 0.5293 (7) | 0.083 (3) | 0.339 (6) |
C15D | 0.8356 (19) | 0.8907 (10) | 0.5852 (9) | 0.072 (3) | 0.339 (6) |
C16D | 0.8392 (18) | 0.8858 (10) | 0.6566 (11) | 0.093 (4) | 0.339 (6) |
H16D | 0.725040 | 0.863845 | 0.669272 | 0.112* | 0.339 (6) |
C17D | 1.013 (3) | 0.9138 (10) | 0.7091 (6) | 0.093 (4) | 0.339 (6) |
H17D | 1.015712 | 0.910545 | 0.756882 | 0.112* | 0.339 (6) |
C18D | 1.1839 (19) | 0.9466 (10) | 0.6901 (8) | 0.104 (5) | 0.339 (6) |
H18D | 1.300469 | 0.965352 | 0.725262 | 0.124* | 0.339 (6) |
C19D | 1.1804 (18) | 0.9515 (11) | 0.6187 (11) | 0.113 (5) | 0.339 (6) |
H19D | 1.294556 | 0.973460 | 0.606031 | 0.136* | 0.339 (6) |
C20D | 1.006 (3) | 0.9235 (12) | 0.5662 (6) | 0.096 (4) | 0.339 (6) |
H20D | 1.003885 | 0.926762 | 0.518420 | 0.115* | 0.339 (6) |
O3D | 0.6689 (19) | 0.8790 (7) | 0.4661 (6) | 0.079 (3) | 0.339 (6) |
O4D | 0.5080 (18) | 0.8298 (9) | 0.5407 (6) | 0.139 (5) | 0.339 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1A | 0.082 (2) | 0.0410 (17) | 0.081 (2) | 0.0079 (16) | 0.0187 (19) | 0.0279 (16) |
C2A | 0.0599 (19) | 0.0410 (17) | 0.0619 (19) | 0.0019 (14) | 0.0021 (16) | 0.0213 (14) |
C6A | 0.0518 (17) | 0.0407 (16) | 0.0654 (19) | −0.0048 (13) | 0.0018 (14) | 0.0252 (14) |
C3A | 0.0515 (17) | 0.0377 (15) | 0.0538 (17) | −0.0053 (13) | −0.0075 (13) | 0.0176 (13) |
C4A | 0.075 (2) | 0.0353 (16) | 0.067 (2) | 0.0000 (15) | −0.0002 (17) | 0.0158 (14) |
C5A | 0.098 (3) | 0.045 (2) | 0.099 (3) | 0.0096 (19) | 0.028 (2) | 0.0174 (19) |
C7A | 0.0519 (19) | 0.062 (2) | 0.097 (3) | −0.0067 (16) | 0.0034 (18) | 0.034 (2) |
C8A | 0.0619 (19) | 0.0423 (16) | 0.0616 (19) | −0.0037 (14) | 0.0047 (15) | 0.0261 (14) |
C9A | 0.065 (2) | 0.057 (2) | 0.072 (2) | −0.0024 (16) | −0.0038 (17) | 0.0322 (17) |
C10A | 0.080 (3) | 0.074 (3) | 0.092 (3) | −0.016 (2) | −0.024 (2) | 0.047 (2) |
C11A | 0.125 (4) | 0.093 (3) | 0.062 (3) | −0.035 (3) | −0.020 (3) | 0.042 (2) |
C12A | 0.134 (5) | 0.099 (4) | 0.061 (3) | −0.004 (3) | 0.009 (3) | 0.023 (2) |
C13A | 0.084 (3) | 0.082 (3) | 0.073 (3) | 0.008 (2) | 0.013 (2) | 0.027 (2) |
C5B | 0.073 (2) | 0.064 (2) | 0.107 (3) | −0.0018 (18) | 0.020 (2) | 0.043 (2) |
C4B | 0.0521 (18) | 0.056 (2) | 0.073 (2) | 0.0013 (15) | 0.0055 (16) | 0.0262 (16) |
C3B | 0.0529 (17) | 0.0436 (16) | 0.0526 (16) | 0.0054 (13) | 0.0018 (14) | 0.0212 (13) |
C6B | 0.0614 (19) | 0.0404 (16) | 0.0644 (19) | 0.0082 (14) | 0.0101 (15) | 0.0217 (14) |
C7B | 0.090 (3) | 0.052 (2) | 0.083 (2) | 0.0200 (18) | 0.004 (2) | 0.0297 (18) |
C8B | 0.0645 (19) | 0.0435 (17) | 0.0562 (17) | 0.0099 (14) | 0.0134 (15) | 0.0171 (14) |
C13B | 0.109 (3) | 0.061 (2) | 0.081 (3) | 0.032 (2) | −0.011 (2) | 0.006 (2) |
C12B | 0.151 (5) | 0.076 (3) | 0.089 (3) | 0.040 (3) | −0.028 (3) | −0.010 (2) |
C11B | 0.104 (3) | 0.091 (3) | 0.066 (2) | 0.024 (3) | −0.011 (2) | 0.007 (2) |
C10B | 0.082 (3) | 0.079 (3) | 0.077 (2) | 0.027 (2) | −0.002 (2) | 0.024 (2) |
C9B | 0.077 (2) | 0.050 (2) | 0.074 (2) | 0.0149 (17) | 0.0007 (18) | 0.0138 (17) |
C2B | 0.077 (2) | 0.0447 (18) | 0.066 (2) | 0.0031 (16) | 0.0133 (17) | 0.0249 (15) |
C1B | 0.085 (3) | 0.054 (2) | 0.084 (2) | 0.0020 (18) | 0.032 (2) | 0.0234 (18) |
N1A | 0.0557 (15) | 0.0389 (13) | 0.0590 (15) | −0.0014 (11) | 0.0023 (12) | 0.0229 (11) |
N2A | 0.0564 (15) | 0.0360 (13) | 0.0583 (14) | 0.0016 (11) | 0.0047 (12) | 0.0199 (11) |
N3A | 0.0611 (16) | 0.0358 (13) | 0.0615 (16) | 0.0002 (12) | 0.0074 (13) | 0.0189 (12) |
N1B | 0.0659 (16) | 0.0385 (13) | 0.0576 (15) | 0.0036 (11) | 0.0121 (12) | 0.0196 (11) |
N2B | 0.0680 (17) | 0.0386 (13) | 0.0544 (14) | 0.0030 (12) | 0.0096 (13) | 0.0200 (11) |
N3B | 0.0613 (17) | 0.0411 (14) | 0.0644 (16) | 0.0038 (12) | 0.0119 (13) | 0.0210 (12) |
O1A | 0.0828 (17) | 0.0490 (13) | 0.0951 (18) | 0.0128 (12) | 0.0308 (15) | 0.0305 (12) |
O2A | 0.106 (2) | 0.0383 (13) | 0.108 (2) | −0.0094 (13) | 0.0260 (17) | 0.0185 (13) |
O1B | 0.1010 (19) | 0.0472 (14) | 0.0968 (19) | 0.0003 (13) | 0.0338 (15) | 0.0304 (13) |
O2B | 0.0716 (17) | 0.0696 (18) | 0.141 (3) | 0.0123 (14) | 0.0387 (17) | 0.0395 (18) |
S1A | 0.0671 (5) | 0.0373 (4) | 0.0682 (5) | −0.0104 (3) | 0.0025 (4) | 0.0201 (4) |
S1B | 0.0620 (5) | 0.0485 (5) | 0.0884 (7) | 0.0101 (4) | 0.0214 (5) | 0.0231 (4) |
C14A | 0.124 (7) | 0.141 (7) | 0.074 (6) | −0.007 (6) | −0.023 (5) | 0.021 (5) |
C15A | 0.120 (7) | 0.113 (6) | 0.078 (5) | −0.017 (5) | −0.029 (5) | 0.020 (5) |
C16A | 0.181 (7) | 0.174 (7) | 0.131 (6) | −0.015 (7) | −0.035 (6) | 0.029 (6) |
C17A | 0.193 (10) | 0.194 (9) | 0.106 (7) | −0.027 (8) | −0.068 (7) | 0.029 (7) |
C18A | 0.220 (12) | 0.186 (11) | 0.090 (7) | −0.049 (10) | −0.044 (8) | 0.058 (7) |
C19A | 0.208 (11) | 0.159 (9) | 0.089 (6) | −0.044 (8) | −0.003 (7) | 0.053 (6) |
C20A | 0.188 (10) | 0.130 (8) | 0.089 (6) | −0.027 (7) | 0.001 (6) | 0.046 (6) |
O3A | 0.097 (6) | 0.141 (7) | 0.063 (4) | −0.025 (5) | −0.008 (4) | 0.041 (4) |
O4A | 0.241 (16) | 0.301 (16) | 0.181 (14) | −0.081 (14) | −0.011 (12) | −0.026 (13) |
C14C | 0.113 (8) | 0.165 (9) | 0.072 (7) | −0.030 (7) | −0.020 (6) | 0.043 (7) |
C15C | 0.143 (8) | 0.130 (7) | 0.075 (6) | −0.036 (6) | −0.035 (5) | 0.046 (5) |
C16C | 0.100 (6) | 0.097 (6) | 0.072 (5) | 0.004 (5) | −0.015 (5) | 0.033 (5) |
C17C | 0.145 (8) | 0.136 (8) | 0.078 (6) | 0.008 (7) | −0.018 (6) | 0.059 (6) |
C18C | 0.195 (11) | 0.151 (9) | 0.113 (7) | −0.007 (8) | −0.052 (8) | 0.059 (7) |
C19C | 0.221 (10) | 0.163 (9) | 0.125 (8) | −0.058 (8) | −0.062 (8) | 0.067 (7) |
C20C | 0.199 (10) | 0.142 (9) | 0.126 (8) | −0.065 (8) | −0.077 (8) | 0.071 (7) |
O3C | 0.087 (6) | 0.116 (6) | 0.063 (5) | −0.021 (5) | −0.014 (4) | 0.047 (4) |
O4C | 0.114 (8) | 0.234 (14) | 0.110 (9) | −0.007 (8) | −0.009 (7) | −0.001 (9) |
C14B | 0.079 (5) | 0.095 (4) | 0.079 (5) | 0.005 (4) | 0.006 (4) | 0.038 (4) |
C15B | 0.059 (4) | 0.073 (4) | 0.083 (4) | −0.001 (3) | 0.001 (3) | 0.027 (3) |
C16B | 0.088 (4) | 0.085 (4) | 0.077 (5) | 0.000 (4) | −0.010 (4) | 0.029 (4) |
C17B | 0.089 (6) | 0.099 (5) | 0.086 (5) | −0.009 (4) | −0.013 (4) | 0.030 (4) |
C18B | 0.085 (6) | 0.105 (5) | 0.078 (4) | 0.004 (5) | −0.004 (4) | 0.031 (4) |
C19B | 0.085 (5) | 0.163 (6) | 0.092 (7) | −0.002 (5) | −0.014 (5) | 0.033 (6) |
C20B | 0.082 (6) | 0.150 (6) | 0.087 (5) | −0.008 (5) | −0.009 (4) | 0.039 (5) |
O3B | 0.076 (3) | 0.119 (4) | 0.062 (3) | 0.006 (3) | 0.000 (3) | 0.018 (3) |
O4B | 0.100 (4) | 0.248 (8) | 0.107 (4) | −0.043 (4) | −0.012 (3) | 0.092 (5) |
C14D | 0.078 (6) | 0.089 (6) | 0.078 (6) | 0.006 (6) | 0.014 (6) | 0.027 (5) |
C15D | 0.078 (6) | 0.074 (6) | 0.069 (6) | 0.007 (6) | 0.002 (6) | 0.034 (5) |
C16D | 0.083 (7) | 0.100 (7) | 0.089 (8) | −0.006 (6) | −0.026 (7) | 0.039 (7) |
C17D | 0.085 (9) | 0.103 (7) | 0.087 (6) | −0.009 (8) | −0.011 (7) | 0.041 (6) |
C18D | 0.082 (8) | 0.134 (9) | 0.082 (9) | 0.008 (8) | −0.012 (8) | 0.031 (8) |
C19D | 0.088 (8) | 0.151 (8) | 0.084 (9) | 0.002 (7) | −0.019 (7) | 0.034 (8) |
C20D | 0.069 (8) | 0.123 (7) | 0.085 (6) | 0.007 (7) | −0.009 (6) | 0.030 (6) |
O3D | 0.069 (7) | 0.095 (6) | 0.071 (6) | −0.004 (5) | 0.003 (5) | 0.033 (5) |
O4D | 0.114 (8) | 0.198 (12) | 0.100 (8) | −0.038 (8) | 0.002 (6) | 0.062 (8) |
C1A—C2A | 1.499 (5) | C2B—C1B | 1.488 (5) |
C1A—H1A1 | 0.9600 | C1B—H1B1 | 0.9600 |
C1A—H1A2 | 0.9600 | C1B—H1B2 | 0.9600 |
C1A—H1A3 | 0.9600 | C1B—H1B3 | 0.9600 |
C2A—O1A | 1.236 (4) | N1A—N2A | 1.400 (4) |
C2A—N1A | 1.341 (4) | N3A—H3A | 0.84 (3) |
C6A—N1A | 1.503 (4) | N1B—N2B | 1.408 (3) |
C6A—C7A | 1.512 (5) | N3B—H3B | 0.85 (4) |
C6A—C8A | 1.533 (4) | C14A—O4A | 1.239 (16) |
C6A—S1A | 1.844 (3) | C14A—O3A | 1.312 (13) |
C3A—N2A | 1.282 (4) | C14A—C15A | 1.526 (11) |
C3A—N3A | 1.373 (4) | C15A—C16A | 1.3900 |
C3A—S1A | 1.740 (3) | C15A—C20A | 1.3900 |
C4A—O2A | 1.212 (4) | C16A—C17A | 1.3900 |
C4A—N3A | 1.366 (4) | C16A—H16A | 0.9300 |
C4A—C5A | 1.485 (5) | C17A—C18A | 1.3900 |
C5A—H5A1 | 0.9600 | C17A—H17A | 0.9300 |
C5A—H5A2 | 0.9600 | C18A—C19A | 1.3900 |
C5A—H5A3 | 0.9600 | C18A—H18A | 0.9300 |
C7A—H7A1 | 0.9600 | C19A—C20A | 1.3900 |
C7A—H7A2 | 0.9600 | C19A—H19A | 0.9300 |
C7A—H7A3 | 0.9600 | C20A—H20A | 0.9300 |
C8A—C9A | 1.376 (5) | C14C—O4C | 1.171 (15) |
C8A—C13A | 1.382 (5) | C14C—O3C | 1.370 (15) |
C9A—C10A | 1.389 (5) | C14C—C15C | 1.517 (13) |
C9A—H9A | 0.9300 | C15C—C16C | 1.3900 |
C10A—C11A | 1.374 (7) | C15C—C20C | 1.3900 |
C10A—H10A | 0.9300 | C16C—C17C | 1.3900 |
C11A—C12A | 1.369 (7) | C16C—H16C | 0.9300 |
C11A—O3A | 1.407 (10) | C17C—C18C | 1.3900 |
C11A—O3C | 1.473 (11) | C17C—H17C | 0.9300 |
C12A—C13A | 1.364 (6) | C18C—C19C | 1.3900 |
C12A—H12A | 0.9300 | C18C—H18C | 0.9300 |
C13A—H13A | 0.9300 | C19C—C20C | 1.3900 |
C5B—C4B | 1.487 (5) | C19C—H19C | 0.9300 |
C5B—H5B1 | 0.9600 | C20C—H20C | 0.9300 |
C5B—H5B2 | 0.9600 | C14B—O4B | 1.170 (9) |
C5B—H5B3 | 0.9600 | C14B—O3B | 1.318 (9) |
C4B—O2B | 1.216 (4) | C14B—C15B | 1.476 (9) |
C4B—N3B | 1.357 (4) | C15B—C16B | 1.3900 |
C3B—N2B | 1.275 (4) | C15B—C20B | 1.3900 |
C3B—N3B | 1.387 (4) | C16B—C17B | 1.3900 |
C3B—S1B | 1.735 (3) | C16B—H16B | 0.9300 |
C6B—N1B | 1.492 (4) | C17B—C18B | 1.3900 |
C6B—C8B | 1.525 (5) | C17B—H17B | 0.9300 |
C6B—C7B | 1.525 (4) | C18B—C19B | 1.3900 |
C6B—S1B | 1.849 (3) | C18B—H18B | 0.9300 |
C7B—H7B1 | 0.9600 | C19B—C20B | 1.3900 |
C7B—H7B2 | 0.9600 | C19B—H19B | 0.9300 |
C7B—H7B3 | 0.9600 | C20B—H20B | 0.9300 |
C8B—C13B | 1.368 (5) | C14D—O4D | 1.190 (13) |
C8B—C9B | 1.372 (5) | C14D—O3D | 1.336 (13) |
C13B—C12B | 1.380 (6) | C14D—C15D | 1.456 (13) |
C13B—H13B | 0.9300 | C15D—C16D | 1.3900 |
C12B—C11B | 1.355 (6) | C15D—C20D | 1.3900 |
C12B—H12B | 0.9300 | C16D—C17D | 1.3900 |
C11B—C10B | 1.360 (6) | C16D—H16D | 0.9300 |
C11B—O3B | 1.396 (7) | C17D—C18D | 1.3900 |
C11B—O3D | 1.551 (13) | C17D—H17D | 0.9300 |
C10B—C9B | 1.376 (5) | C18D—C19D | 1.3900 |
C10B—H10B | 0.9300 | C18D—H18D | 0.9300 |
C9B—H9B | 0.9300 | C19D—C20D | 1.3900 |
C2B—O1B | 1.236 (4) | C19D—H19D | 0.9300 |
C2B—N1B | 1.344 (4) | C20D—H20D | 0.9300 |
C2A—C1A—H1A1 | 109.5 | H1B2—C1B—H1B3 | 109.5 |
C2A—C1A—H1A2 | 109.5 | C2A—N1A—N2A | 118.7 (2) |
H1A1—C1A—H1A2 | 109.5 | C2A—N1A—C6A | 124.3 (3) |
C2A—C1A—H1A3 | 109.5 | N2A—N1A—C6A | 116.3 (2) |
H1A1—C1A—H1A3 | 109.5 | C3A—N2A—N1A | 110.0 (2) |
H1A2—C1A—H1A3 | 109.5 | C4A—N3A—C3A | 125.3 (3) |
O1A—C2A—N1A | 120.5 (3) | C4A—N3A—H3A | 109 (2) |
O1A—C2A—C1A | 121.6 (3) | C3A—N3A—H3A | 125 (2) |
N1A—C2A—C1A | 117.9 (3) | C2B—N1B—N2B | 118.8 (3) |
N1A—C6A—C7A | 112.8 (3) | C2B—N1B—C6B | 123.3 (3) |
N1A—C6A—C8A | 108.2 (2) | N2B—N1B—C6B | 116.6 (2) |
C7A—C6A—C8A | 115.0 (3) | C3B—N2B—N1B | 109.9 (2) |
N1A—C6A—S1A | 101.4 (2) | C4B—N3B—C3B | 124.4 (3) |
C7A—C6A—S1A | 106.6 (2) | C4B—N3B—H3B | 122 (3) |
C8A—C6A—S1A | 112.1 (2) | C3B—N3B—H3B | 114 (3) |
N2A—C3A—N3A | 119.0 (3) | C3A—S1A—C6A | 89.90 (14) |
N2A—C3A—S1A | 118.5 (2) | C3B—S1B—C6B | 89.66 (14) |
N3A—C3A—S1A | 122.5 (2) | O4A—C14A—O3A | 110.2 (13) |
O2A—C4A—N3A | 121.1 (3) | O4A—C14A—C15A | 126.8 (15) |
O2A—C4A—C5A | 124.0 (3) | O3A—C14A—C15A | 109.7 (10) |
N3A—C4A—C5A | 114.8 (3) | C16A—C15A—C20A | 120.0 |
C4A—C5A—H5A1 | 109.5 | C16A—C15A—C14A | 119.7 (7) |
C4A—C5A—H5A2 | 109.5 | C20A—C15A—C14A | 118.4 (8) |
H5A1—C5A—H5A2 | 109.5 | C15A—C16A—C17A | 120.0 |
C4A—C5A—H5A3 | 109.5 | C15A—C16A—H16A | 120.0 |
H5A1—C5A—H5A3 | 109.5 | C17A—C16A—H16A | 120.0 |
H5A2—C5A—H5A3 | 109.5 | C18A—C17A—C16A | 120.0 |
C6A—C7A—H7A1 | 109.5 | C18A—C17A—H17A | 120.0 |
C6A—C7A—H7A2 | 109.5 | C16A—C17A—H17A | 120.0 |
H7A1—C7A—H7A2 | 109.5 | C17A—C18A—C19A | 120.0 |
C6A—C7A—H7A3 | 109.5 | C17A—C18A—H18A | 120.0 |
H7A1—C7A—H7A3 | 109.5 | C19A—C18A—H18A | 120.0 |
H7A2—C7A—H7A3 | 109.5 | C20A—C19A—C18A | 120.0 |
C9A—C8A—C13A | 117.6 (3) | C20A—C19A—H19A | 120.0 |
C9A—C8A—C6A | 121.0 (3) | C18A—C19A—H19A | 120.0 |
C13A—C8A—C6A | 121.1 (3) | C19A—C20A—C15A | 120.0 |
C8A—C9A—C10A | 121.2 (4) | C19A—C20A—H20A | 120.0 |
C8A—C9A—H9A | 119.4 | C15A—C20A—H20A | 120.0 |
C10A—C9A—H9A | 119.4 | C14A—O3A—C11A | 117.1 (8) |
C11A—C10A—C9A | 119.2 (4) | O4C—C14C—O3C | 111.6 (14) |
C11A—C10A—H10A | 120.4 | O4C—C14C—C15C | 111.8 (14) |
C9A—C10A—H10A | 120.4 | O3C—C14C—C15C | 107.0 (12) |
C12A—C11A—C10A | 120.3 (4) | C16C—C15C—C20C | 120.0 |
C12A—C11A—O3A | 104.9 (6) | C16C—C15C—C14C | 109.1 (8) |
C10A—C11A—O3A | 134.7 (6) | C20C—C15C—C14C | 125.1 (7) |
C12A—C11A—O3C | 136.1 (6) | C15C—C16C—C17C | 120.0 |
C10A—C11A—O3C | 103.5 (6) | C15C—C16C—H16C | 120.0 |
C13A—C12A—C11A | 119.7 (5) | C17C—C16C—H16C | 120.0 |
C13A—C12A—H12A | 120.2 | C16C—C17C—C18C | 120.0 |
C11A—C12A—H12A | 120.2 | C16C—C17C—H17C | 120.0 |
C12A—C13A—C8A | 121.9 (4) | C18C—C17C—H17C | 120.0 |
C12A—C13A—H13A | 119.0 | C17C—C18C—C19C | 120.0 |
C8A—C13A—H13A | 119.0 | C17C—C18C—H18C | 120.0 |
C4B—C5B—H5B1 | 109.5 | C19C—C18C—H18C | 120.0 |
C4B—C5B—H5B2 | 109.5 | C20C—C19C—C18C | 120.0 |
H5B1—C5B—H5B2 | 109.5 | C20C—C19C—H19C | 120.0 |
C4B—C5B—H5B3 | 109.5 | C18C—C19C—H19C | 120.0 |
H5B1—C5B—H5B3 | 109.5 | C19C—C20C—C15C | 120.0 |
H5B2—C5B—H5B3 | 109.5 | C19C—C20C—H20C | 120.0 |
O2B—C4B—N3B | 121.3 (3) | C15C—C20C—H20C | 120.0 |
O2B—C4B—C5B | 122.8 (3) | C14C—O3C—C11A | 127.5 (9) |
N3B—C4B—C5B | 115.8 (3) | O4B—C14B—O3B | 121.2 (8) |
N2B—C3B—N3B | 119.3 (3) | O4B—C14B—C15B | 125.6 (8) |
N2B—C3B—S1B | 119.1 (2) | O3B—C14B—C15B | 113.1 (7) |
N3B—C3B—S1B | 121.5 (2) | C16B—C15B—C20B | 120.0 |
N1B—C6B—C8B | 110.0 (2) | C16B—C15B—C14B | 121.5 (8) |
N1B—C6B—C7B | 112.3 (3) | C20B—C15B—C14B | 118.5 (8) |
C8B—C6B—C7B | 114.9 (3) | C17B—C16B—C15B | 120.0 |
N1B—C6B—S1B | 102.0 (2) | C17B—C16B—H16B | 120.0 |
C8B—C6B—S1B | 110.0 (2) | C15B—C16B—H16B | 120.0 |
C7B—C6B—S1B | 106.8 (2) | C16B—C17B—C18B | 120.0 |
C6B—C7B—H7B1 | 109.5 | C16B—C17B—H17B | 120.0 |
C6B—C7B—H7B2 | 109.5 | C18B—C17B—H17B | 120.0 |
H7B1—C7B—H7B2 | 109.5 | C19B—C18B—C17B | 120.0 |
C6B—C7B—H7B3 | 109.5 | C19B—C18B—H18B | 120.0 |
H7B1—C7B—H7B3 | 109.5 | C17B—C18B—H18B | 120.0 |
H7B2—C7B—H7B3 | 109.5 | C18B—C19B—C20B | 120.0 |
C13B—C8B—C9B | 118.3 (3) | C18B—C19B—H19B | 120.0 |
C13B—C8B—C6B | 121.5 (3) | C20B—C19B—H19B | 120.0 |
C9B—C8B—C6B | 120.2 (3) | C19B—C20B—C15B | 120.0 |
C8B—C13B—C12B | 120.7 (4) | C19B—C20B—H20B | 120.0 |
C8B—C13B—H13B | 119.6 | C15B—C20B—H20B | 120.0 |
C12B—C13B—H13B | 119.6 | C14B—O3B—C11B | 112.7 (7) |
C11B—C12B—C13B | 119.8 (4) | O4D—C14D—O3D | 124.1 (14) |
C11B—C12B—H12B | 120.1 | O4D—C14D—C15D | 121.6 (14) |
C13B—C12B—H12B | 120.1 | O3D—C14D—C15D | 114.3 (13) |
C12B—C11B—C10B | 120.7 (4) | C16D—C15D—C20D | 120.0 |
C12B—C11B—O3B | 118.9 (4) | C16D—C15D—C14D | 121.3 (16) |
C10B—C11B—O3B | 118.4 (5) | C20D—C15D—C14D | 118.7 (16) |
C12B—C11B—O3D | 116.0 (6) | C17D—C16D—C15D | 120.0 |
C10B—C11B—O3D | 118.4 (6) | C17D—C16D—H16D | 120.0 |
C11B—C10B—C9B | 119.1 (4) | C15D—C16D—H16D | 120.0 |
C11B—C10B—H10B | 120.4 | C16D—C17D—C18D | 120.0 |
C9B—C10B—H10B | 120.4 | C16D—C17D—H17D | 120.0 |
C8B—C9B—C10B | 121.4 (3) | C18D—C17D—H17D | 120.0 |
C8B—C9B—H9B | 119.3 | C19D—C18D—C17D | 120.0 |
C10B—C9B—H9B | 119.3 | C19D—C18D—H18D | 120.0 |
O1B—C2B—N1B | 119.7 (3) | C17D—C18D—H18D | 120.0 |
O1B—C2B—C1B | 122.1 (3) | C18D—C19D—C20D | 120.0 |
N1B—C2B—C1B | 118.2 (3) | C18D—C19D—H19D | 120.0 |
C2B—C1B—H1B1 | 109.5 | C20D—C19D—H19D | 120.0 |
C2B—C1B—H1B2 | 109.5 | C19D—C20D—C15D | 120.0 |
H1B1—C1B—H1B2 | 109.5 | C19D—C20D—H20D | 120.0 |
C2B—C1B—H1B3 | 109.5 | C15D—C20D—H20D | 120.0 |
H1B1—C1B—H1B3 | 109.5 | C14D—O3D—C11B | 104.3 (10) |
N1A—C6A—C8A—C9A | −80.2 (3) | N3A—C3A—S1A—C6A | 170.4 (3) |
C7A—C6A—C8A—C9A | 152.7 (3) | N1A—C6A—S1A—C3A | 15.58 (19) |
S1A—C6A—C8A—C9A | 30.8 (3) | C7A—C6A—S1A—C3A | 133.8 (2) |
N1A—C6A—C8A—C13A | 94.1 (4) | C8A—C6A—S1A—C3A | −99.6 (2) |
C7A—C6A—C8A—C13A | −33.0 (4) | N2B—C3B—S1B—C6B | −9.2 (3) |
S1A—C6A—C8A—C13A | −155.0 (3) | N3B—C3B—S1B—C6B | 169.8 (3) |
C13A—C8A—C9A—C10A | 1.2 (5) | N1B—C6B—S1B—C3B | 13.5 (2) |
C6A—C8A—C9A—C10A | 175.7 (3) | C8B—C6B—S1B—C3B | −103.2 (2) |
C8A—C9A—C10A—C11A | −1.4 (6) | C7B—C6B—S1B—C3B | 131.5 (2) |
C9A—C10A—C11A—C12A | 1.2 (6) | O4A—C14A—C15A—C16A | −68 (2) |
C9A—C10A—C11A—O3A | 177.2 (7) | O3A—C14A—C15A—C16A | 155.3 (9) |
C9A—C10A—C11A—O3C | 178.7 (5) | O4A—C14A—C15A—C20A | 96 (2) |
C10A—C11A—C12A—C13A | −0.8 (7) | O3A—C14A—C15A—C20A | −40.2 (14) |
O3A—C11A—C12A—C13A | −177.9 (6) | C20A—C15A—C16A—C17A | 0.0 |
O3C—C11A—C12A—C13A | −177.4 (7) | C14A—C15A—C16A—C17A | 164.3 (10) |
C11A—C12A—C13A—C8A | 0.7 (7) | C15A—C16A—C17A—C18A | 0.0 |
C9A—C8A—C13A—C12A | −0.9 (6) | C16A—C17A—C18A—C19A | 0.0 |
C6A—C8A—C13A—C12A | −175.4 (4) | C17A—C18A—C19A—C20A | 0.0 |
N1B—C6B—C8B—C13B | 148.5 (4) | C18A—C19A—C20A—C15A | 0.0 |
C7B—C6B—C8B—C13B | 20.6 (5) | C16A—C15A—C20A—C19A | 0.0 |
S1B—C6B—C8B—C13B | −100.0 (4) | C14A—C15A—C20A—C19A | −164.5 (9) |
N1B—C6B—C8B—C9B | −33.4 (4) | O4A—C14A—O3A—C11A | 41 (2) |
C7B—C6B—C8B—C9B | −161.2 (3) | C15A—C14A—O3A—C11A | −174.9 (9) |
S1B—C6B—C8B—C9B | 78.1 (4) | C12A—C11A—O3A—C14A | −143.6 (10) |
C9B—C8B—C13B—C12B | −2.2 (7) | C10A—C11A—O3A—C14A | 40.0 (14) |
C6B—C8B—C13B—C12B | 175.9 (5) | O4C—C14C—C15C—C16C | −175.6 (14) |
C8B—C13B—C12B—C11B | 1.7 (9) | O3C—C14C—C15C—C16C | 61.9 (14) |
C13B—C12B—C11B—C10B | −0.7 (10) | O4C—C14C—C15C—C20C | −23 (2) |
C13B—C12B—C11B—O3B | −164.8 (6) | O3C—C14C—C15C—C20C | −145.4 (9) |
C13B—C12B—C11B—O3D | 154.3 (7) | C20C—C15C—C16C—C17C | 0.0 |
C12B—C11B—C10B—C9B | 0.3 (8) | C14C—C15C—C16C—C17C | 154.3 (10) |
O3B—C11B—C10B—C9B | 164.5 (5) | C15C—C16C—C17C—C18C | 0.0 |
O3D—C11B—C10B—C9B | −154.2 (6) | C16C—C17C—C18C—C19C | 0.0 |
C13B—C8B—C9B—C10B | 1.8 (6) | C17C—C18C—C19C—C20C | 0.0 |
C6B—C8B—C9B—C10B | −176.4 (4) | C18C—C19C—C20C—C15C | 0.0 |
C11B—C10B—C9B—C8B | −0.8 (7) | C16C—C15C—C20C—C19C | 0.0 |
O1A—C2A—N1A—N2A | −175.8 (3) | C14C—C15C—C20C—C19C | −149.9 (12) |
C1A—C2A—N1A—N2A | 5.0 (4) | O4C—C14C—O3C—C11A | 29 (2) |
O1A—C2A—N1A—C6A | −5.8 (5) | C15C—C14C—O3C—C11A | 151.5 (11) |
C1A—C2A—N1A—C6A | 175.1 (3) | C12A—C11A—O3C—C14C | −132.4 (13) |
C7A—C6A—N1A—C2A | 55.1 (4) | C10A—C11A—O3C—C14C | 50.7 (15) |
C8A—C6A—N1A—C2A | −73.2 (4) | O4B—C14B—C15B—C16B | −175.2 (9) |
S1A—C6A—N1A—C2A | 168.7 (2) | O3B—C14B—C15B—C16B | 8.9 (10) |
C7A—C6A—N1A—N2A | −134.7 (3) | O4B—C14B—C15B—C20B | 3.8 (13) |
C8A—C6A—N1A—N2A | 97.0 (3) | O3B—C14B—C15B—C20B | −172.2 (6) |
S1A—C6A—N1A—N2A | −21.0 (3) | C20B—C15B—C16B—C17B | 0.0 |
N3A—C3A—N2A—N1A | 178.5 (2) | C14B—C15B—C16B—C17B | 178.9 (8) |
S1A—C3A—N2A—N1A | −1.5 (3) | C15B—C16B—C17B—C18B | 0.0 |
C2A—N1A—N2A—C3A | −173.3 (3) | C16B—C17B—C18B—C19B | 0.0 |
C6A—N1A—N2A—C3A | 15.9 (3) | C17B—C18B—C19B—C20B | 0.0 |
O2A—C4A—N3A—C3A | 3.5 (5) | C18B—C19B—C20B—C15B | 0.0 |
C5A—C4A—N3A—C3A | −175.3 (3) | C16B—C15B—C20B—C19B | 0.0 |
N2A—C3A—N3A—C4A | −175.4 (3) | C14B—C15B—C20B—C19B | −178.9 (7) |
S1A—C3A—N3A—C4A | 4.6 (4) | O4B—C14B—O3B—C11B | 4.4 (12) |
O1B—C2B—N1B—N2B | −175.6 (3) | C15B—C14B—O3B—C11B | −179.4 (6) |
C1B—C2B—N1B—N2B | 3.8 (5) | C12B—C11B—O3B—C14B | −110.0 (7) |
O1B—C2B—N1B—C6B | −8.8 (5) | C10B—C11B—O3B—C14B | 85.6 (8) |
C1B—C2B—N1B—C6B | 170.5 (3) | O4D—C14D—C15D—C16D | −5 (2) |
C8B—C6B—N1B—C2B | −67.7 (4) | O3D—C14D—C15D—C16D | 173.9 (11) |
C7B—C6B—N1B—C2B | 61.6 (4) | O4D—C14D—C15D—C20D | 175.6 (14) |
S1B—C6B—N1B—C2B | 175.6 (3) | O3D—C14D—C15D—C20D | −5.3 (17) |
C8B—C6B—N1B—N2B | 99.4 (3) | C20D—C15D—C16D—C17D | 0.0 |
C7B—C6B—N1B—N2B | −131.4 (3) | C14D—C15D—C16D—C17D | −179.2 (15) |
S1B—C6B—N1B—N2B | −17.4 (3) | C15D—C16D—C17D—C18D | 0.0 |
N3B—C3B—N2B—N1B | −178.7 (3) | C16D—C17D—C18D—C19D | 0.0 |
S1B—C3B—N2B—N1B | 0.3 (3) | C17D—C18D—C19D—C20D | 0.0 |
C2B—N1B—N2B—C3B | 179.9 (3) | C18D—C19D—C20D—C15D | 0.0 |
C6B—N1B—N2B—C3B | 12.3 (4) | C16D—C15D—C20D—C19D | 0.0 |
O2B—C4B—N3B—C3B | 4.4 (5) | C14D—C15D—C20D—C19D | 179.2 (15) |
C5B—C4B—N3B—C3B | −174.5 (3) | O4D—C14D—O3D—C11B | −4.6 (19) |
N2B—C3B—N3B—C4B | −171.1 (3) | C15D—C14D—O3D—C11B | 176.4 (11) |
S1B—C3B—N3B—C4B | 10.0 (4) | C12B—C11B—O3D—C14D | 110.4 (10) |
N2A—C3A—S1A—C6A | −9.6 (2) | C10B—C11B—O3D—C14D | −94.0 (10) |
Cg2, Cg3 and Cg6 are the centroids of the C8A–C13A, C15A–C20A and C8B–C13B rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
N3A—H3A···O1Bi | 0.84 (4) | 1.96 (3) | 2.792 (4) | 175 (3) |
N3B—H3B···O1A | 0.84 (4) | 1.99 (5) | 2.801 (4) | 163 (4) |
C5A—H5A2···O1Bi | 0.96 | 2.59 | 3.226 (5) | 124 |
C7A—H7A2···O2Aii | 0.96 | 2.54 | 3.482 (5) | 168 |
C9B—H9B···O2Biii | 0.93 | 2.58 | 3.303 (5) | 135 |
C5B—H5B1···O4Aiv | 0.96 | 2.59 | 3.50 (2) | 158 |
C5B—H5B1···O4Civ | 0.96 | 2.45 | 3.395 (17) | 166 |
C12A—H12A···O4Civ | 0.93 | 2.58 | 3.211 (15) | 125 |
C17B—H17B···Cg2v | 0.93 | 2.91 | 3.664 (8) | 139 |
C17C—H17C···Cg6v | 0.93 | 2.98 | 3.776 (10) | 145 |
C20C—H20C···Cg3vi | 0.93 | 2.64 | 3.521 (11) | 159 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x, −y, −z; (iii) x+1, y, z; (iv) x−1, y, z; (v) −x+1, −y+1, −z+1; (vi) −x+2, −y+1, −z+1. |
C17H21N3O4S·0.25H2O | Z = 4 |
Mr = 367.93 | F(000) = 778 |
Triclinic, P1 | Dx = 1.307 Mg m−3 |
a = 6.7802 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 17.2671 (4) Å | Cell parameters from 7680 reflections |
c = 17.3089 (4) Å | θ = 2.4–25.5° |
α = 108.224 (1)° | µ = 0.20 mm−1 |
β = 99.084 (1)° | T = 293 K |
γ = 96.720 (1)° | BLOCK, colourless |
V = 1870.50 (7) Å3 | 0.30 × 0.25 × 0.20 mm |
Bruker Kappa APEXII CCD diffractometer | 7680 independent reflections |
Radiation source: fine-focus sealed tube | 5737 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
ω and φ scans | θmax = 26.5°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −7→8 |
Tmin = 0.660, Tmax = 0.746 | k = −21→21 |
27060 measured reflections | l = −21→21 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.053 | Hydrogen site location: mixed |
wR(F2) = 0.169 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0901P)2 + 0.734P] where P = (Fo2 + 2Fc2)/3 |
7680 reflections | (Δ/σ)max = 0.002 |
525 parameters | Δρmax = 0.48 e Å−3 |
242 restraints | Δρmin = −0.38 e Å−3 |
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 | Occ. (<1) | |
C10B | 0.6406 (7) | 0.1228 (2) | 0.0560 (2) | 0.1066 (13) | |
H10B | 0.6521 | 0.0767 | 0.0124 | 0.128* | |
C11B | 0.4800 (6) | 0.1636 (3) | 0.0486 (2) | 0.1023 (12) | |
C12B | 0.4677 (5) | 0.2347 (2) | 0.1099 (2) | 0.0826 (9) | |
H12B | 0.3620 | 0.2633 | 0.1030 | 0.099* | |
C13B | 0.6142 (4) | 0.26296 (18) | 0.18174 (17) | 0.0650 (7) | |
H13B | 0.6094 | 0.3123 | 0.2227 | 0.078* | |
C1B | 0.6525 (4) | 0.36366 (16) | 0.43978 (17) | 0.0646 (7) | |
H1B1 | 0.5739 | 0.3916 | 0.4095 | 0.097* | |
H1B2 | 0.7689 | 0.4020 | 0.4766 | 0.097* | |
H1B3 | 0.5709 | 0.3422 | 0.4715 | 0.097* | |
C1A | 0.7780 (4) | 0.59164 (14) | 0.45336 (16) | 0.0571 (6) | |
H1A1 | 0.8151 | 0.5379 | 0.4347 | 0.086* | |
H1A2 | 0.6334 | 0.5865 | 0.4382 | 0.086* | |
H1A3 | 0.8207 | 0.6154 | 0.5127 | 0.086* | |
C2A | 0.8791 (4) | 0.64657 (13) | 0.41369 (14) | 0.0474 (5) | |
C2B | 0.7206 (4) | 0.29410 (15) | 0.38025 (15) | 0.0528 (6) | |
C3A | 0.7214 (3) | 0.82955 (12) | 0.50833 (13) | 0.0411 (5) | |
C3B | 1.0722 (3) | 0.40326 (13) | 0.31134 (13) | 0.0420 (5) | |
C4A | 0.6056 (4) | 0.95076 (14) | 0.59064 (16) | 0.0562 (6) | |
C4B | 1.3254 (4) | 0.49275 (15) | 0.27918 (15) | 0.0517 (5) | |
C5A | 0.4525 (5) | 0.97664 (17) | 0.6418 (2) | 0.0774 (8) | |
H5A1 | 0.4990 | 1.0326 | 0.6787 | 0.116* | |
H5A2 | 0.4339 | 0.9407 | 0.6736 | 0.116* | |
H5A3 | 0.3259 | 0.9732 | 0.6060 | 0.116* | |
C5B | 1.3775 (4) | 0.57778 (17) | 0.27520 (19) | 0.0656 (7) | |
H5B1 | 1.5152 | 0.5870 | 0.2685 | 0.098* | |
H5B2 | 1.3627 | 0.6181 | 0.3257 | 0.098* | |
H5B3 | 1.2880 | 0.5828 | 0.2289 | 0.098* | |
C6B | 0.9311 (4) | 0.25124 (13) | 0.27334 (14) | 0.0477 (5) | |
C6A | 0.9260 (3) | 0.78654 (13) | 0.39637 (14) | 0.0440 (5) | |
C7A | 1.1542 (4) | 0.79518 (16) | 0.40080 (18) | 0.0608 (6) | |
H7A1 | 1.2227 | 0.8052 | 0.4569 | 0.091* | |
H7A2 | 1.1997 | 0.8407 | 0.3836 | 0.091* | |
H7A3 | 1.1839 | 0.7450 | 0.3648 | 0.091* | |
C7B | 1.0076 (5) | 0.18272 (16) | 0.30150 (18) | 0.0659 (7) | |
H7B1 | 1.0912 | 0.2066 | 0.3563 | 0.099* | |
H7B2 | 1.0858 | 0.1542 | 0.2637 | 0.099* | |
H7B3 | 0.8940 | 0.1443 | 0.3022 | 0.099* | |
C8B | 0.7685 (4) | 0.21984 (14) | 0.19451 (15) | 0.0530 (6) | |
C8A | 0.7970 (3) | 0.76385 (13) | 0.30896 (13) | 0.0435 (5) | |
C9A | 0.8586 (4) | 0.71431 (17) | 0.23993 (16) | 0.0621 (6) | |
H9A | 0.9834 | 0.6973 | 0.2465 | 0.075* | |
C9B | 0.7846 (6) | 0.1514 (2) | 0.1291 (2) | 0.0855 (10) | |
H9B | 0.8940 | 0.1244 | 0.1346 | 0.103* | |
C10A | 0.7363 (5) | 0.69025 (18) | 0.16185 (17) | 0.0704 (8) | |
H10A | 0.7798 | 0.6576 | 0.1161 | 0.085* | |
C11A | 0.5527 (4) | 0.71394 (18) | 0.15148 (16) | 0.0634 (7) | |
C12A | 0.4859 (4) | 0.76212 (17) | 0.21818 (16) | 0.0623 (6) | |
H12A | 0.3599 | 0.7781 | 0.2108 | 0.075* | |
C13A | 0.6080 (4) | 0.78648 (15) | 0.29646 (15) | 0.0523 (5) | |
H13A | 0.5626 | 0.8188 | 0.3418 | 0.063* | |
C14A | 0.2528 (5) | 0.6466 (2) | 0.04872 (17) | 0.0773 (9) | |
C15A | 0.1621 (6) | 0.6282 (2) | −0.04174 (18) | 0.0909 (11) | |
H15A | 0.2016 | 0.6777 | −0.0559 | 0.109* | |
C17A | 0.2475 (9) | 0.5587 (3) | −0.0944 (3) | 0.1381 (18) | |
H17D | 0.1983 | 0.5081 | −0.0860 | 0.207* | |
H17E | 0.3930 | 0.5707 | −0.0789 | 0.207* | |
H17F | 0.2059 | 0.5528 | −0.1519 | 0.207* | |
C16A | −0.0658 (7) | 0.6106 (3) | −0.0561 (2) | 0.1227 (16) | |
H16D | −0.1225 | 0.6019 | −0.1132 | 0.184* | |
H16E | −0.1123 | 0.6567 | −0.0209 | 0.184* | |
H16F | −0.1081 | 0.5618 | −0.0432 | 0.184* | |
N1B | 0.8656 (3) | 0.31381 (11) | 0.34072 (11) | 0.0465 (4) | |
N1A | 0.8489 (3) | 0.72603 (10) | 0.43526 (11) | 0.0431 (4) | |
N2A | 0.7133 (3) | 0.75104 (10) | 0.48764 (11) | 0.0432 (4) | |
N2B | 0.9297 (3) | 0.39715 (11) | 0.35052 (11) | 0.0442 (4) | |
N3B | 1.1558 (3) | 0.47934 (11) | 0.31041 (11) | 0.0463 (4) | |
H3B | 1.0984 | 0.5209 | 0.3305 | 0.056* | |
N3A | 0.6051 (3) | 0.86705 (11) | 0.56172 (11) | 0.0462 (4) | |
H3A | 0.5258 | 0.8359 | 0.5784 | 0.055* | |
O1B | 0.6499 (3) | 0.22122 (11) | 0.36685 (13) | 0.0733 (6) | |
O1A | 0.9864 (3) | 0.62179 (10) | 0.36345 (12) | 0.0633 (5) | |
O2A | 0.7210 (4) | 0.99870 (11) | 0.57378 (15) | 0.0877 (7) | |
O2B | 1.4220 (3) | 0.43814 (12) | 0.25612 (14) | 0.0745 (5) | |
O3A | 0.4407 (4) | 0.69246 (15) | 0.07026 (11) | 0.0851 (7) | |
O4A | 0.1729 (4) | 0.62528 (18) | 0.09728 (14) | 0.1077 (9) | |
S1A | 0.88298 (9) | 0.88522 (3) | 0.46752 (4) | 0.04905 (17) | |
S1B | 1.15307 (10) | 0.31302 (4) | 0.25781 (4) | 0.05540 (19) | |
C14B | 0.1788 (9) | 0.0980 (5) | −0.0412 (4) | 0.1041 (19) | 0.723 (5) |
C15B | 0.0485 (11) | 0.0684 (5) | −0.1256 (5) | 0.097 (2) | 0.723 (5) |
H15B | −0.0377 | 0.0159 | −0.1331 | 0.117* | 0.723 (5) |
C16B | −0.0847 (12) | 0.1334 (5) | −0.1207 (5) | 0.143 (3) | 0.723 (5) |
H16A | −0.1765 | 0.1199 | −0.1732 | 0.214* | 0.723 (5) |
H16B | −0.1609 | 0.1350 | −0.0781 | 0.214* | 0.723 (5) |
H16C | −0.0015 | 0.1866 | −0.1077 | 0.214* | 0.723 (5) |
C17B | 0.1577 (13) | 0.0551 (5) | −0.1955 (4) | 0.115 (2) | 0.723 (5) |
H17A | 0.0609 | 0.0361 | −0.2473 | 0.173* | 0.723 (5) |
H17B | 0.2408 | 0.1062 | −0.1901 | 0.173* | 0.723 (5) |
H17C | 0.2417 | 0.0143 | −0.1943 | 0.173* | 0.723 (5) |
O3B | 0.3507 (7) | 0.1413 (3) | −0.0316 (3) | 0.1161 (16) | 0.723 (5) |
O4B | 0.1403 (8) | 0.0725 (5) | 0.0133 (4) | 0.171 (3) | 0.723 (5) |
C14' | 0.262 (2) | 0.1068 (12) | −0.0760 (10) | 0.104 (4) | 0.277 (5) |
C15' | 0.056 (3) | 0.0920 (18) | −0.1333 (12) | 0.117 (6) | 0.277 (5) |
H15' | 0.0300 | 0.1483 | −0.1257 | 0.140* | 0.277 (5) |
C16' | −0.155 (3) | 0.0433 (17) | −0.1396 (14) | 0.177 (8) | 0.277 (5) |
H16G | −0.1870 | 0.0565 | −0.0853 | 0.266* | 0.277 (5) |
H16H | −0.2556 | 0.0582 | −0.1755 | 0.266* | 0.277 (5) |
H16I | −0.1551 | −0.0150 | −0.1619 | 0.266* | 0.277 (5) |
C17' | 0.054 (4) | 0.0580 (17) | −0.2240 (12) | 0.138 (8) | 0.277 (5) |
H17G | −0.0814 | 0.0508 | −0.2550 | 0.208* | 0.277 (5) |
H17H | 0.1433 | 0.0958 | −0.2388 | 0.208* | 0.277 (5) |
H17I | 0.0985 | 0.0055 | −0.2365 | 0.208* | 0.277 (5) |
O3B' | 0.275 (2) | 0.1204 (10) | 0.0005 (7) | 0.138 (4) | 0.277 (5) |
O4B' | 0.418 (2) | 0.1056 (11) | −0.1017 (8) | 0.163 (6) | 0.277 (5) |
O1 | −0.348 (3) | −0.0897 (8) | −0.1929 (9) | 0.240 (5)* | 0.5 |
H1A | −0.36 (3) | −0.138 (5) | −0.231 (7) | 0.288* | 0.5 |
H1B | −0.33 (3) | −0.100 (10) | −0.146 (5) | 0.288* | 0.5 |
U11 | U22 | U33 | U12 | U13 | U23 | |
C10B | 0.116 (3) | 0.092 (3) | 0.081 (2) | 0.028 (2) | 0.005 (2) | −0.0110 (19) |
C11B | 0.090 (3) | 0.110 (3) | 0.073 (2) | 0.010 (2) | −0.0138 (18) | 0.001 (2) |
C12B | 0.0668 (19) | 0.102 (2) | 0.0749 (19) | 0.0302 (17) | 0.0075 (15) | 0.0218 (18) |
C13B | 0.0642 (16) | 0.0689 (17) | 0.0586 (15) | 0.0225 (13) | 0.0118 (12) | 0.0135 (13) |
C1B | 0.0747 (17) | 0.0555 (15) | 0.0730 (17) | 0.0097 (13) | 0.0389 (14) | 0.0239 (13) |
C1A | 0.0748 (16) | 0.0351 (11) | 0.0678 (15) | 0.0116 (11) | 0.0221 (13) | 0.0220 (11) |
C2A | 0.0535 (13) | 0.0343 (11) | 0.0538 (12) | 0.0069 (9) | 0.0090 (11) | 0.0157 (9) |
C2B | 0.0623 (15) | 0.0467 (13) | 0.0574 (13) | 0.0080 (11) | 0.0211 (11) | 0.0249 (11) |
C3A | 0.0437 (11) | 0.0347 (10) | 0.0442 (11) | 0.0033 (8) | 0.0052 (9) | 0.0153 (8) |
C3B | 0.0472 (12) | 0.0401 (11) | 0.0413 (10) | 0.0118 (9) | 0.0097 (9) | 0.0157 (9) |
C4A | 0.0701 (16) | 0.0366 (12) | 0.0609 (14) | 0.0078 (11) | 0.0166 (12) | 0.0142 (10) |
C4B | 0.0469 (13) | 0.0553 (14) | 0.0533 (13) | 0.0037 (11) | 0.0098 (10) | 0.0210 (11) |
C5A | 0.099 (2) | 0.0481 (15) | 0.092 (2) | 0.0249 (15) | 0.0407 (18) | 0.0182 (14) |
C5B | 0.0621 (16) | 0.0624 (16) | 0.0813 (18) | 0.0029 (12) | 0.0224 (14) | 0.0360 (14) |
C6B | 0.0559 (13) | 0.0365 (11) | 0.0554 (13) | 0.0132 (10) | 0.0182 (10) | 0.0172 (10) |
C6A | 0.0427 (11) | 0.0345 (10) | 0.0570 (12) | 0.0038 (8) | 0.0137 (10) | 0.0180 (9) |
C7A | 0.0438 (13) | 0.0513 (14) | 0.0886 (18) | 0.0026 (10) | 0.0184 (12) | 0.0252 (13) |
C7B | 0.0865 (19) | 0.0470 (14) | 0.0730 (17) | 0.0270 (13) | 0.0168 (14) | 0.0268 (12) |
C8B | 0.0578 (14) | 0.0434 (12) | 0.0559 (13) | 0.0124 (10) | 0.0138 (11) | 0.0119 (10) |
C8A | 0.0469 (12) | 0.0365 (10) | 0.0525 (12) | 0.0031 (9) | 0.0166 (10) | 0.0207 (9) |
C9A | 0.0616 (15) | 0.0651 (16) | 0.0653 (16) | 0.0164 (12) | 0.0255 (13) | 0.0219 (13) |
C9B | 0.093 (2) | 0.0699 (19) | 0.076 (2) | 0.0291 (17) | 0.0075 (17) | 0.0004 (16) |
C10A | 0.086 (2) | 0.0720 (18) | 0.0532 (15) | 0.0108 (15) | 0.0282 (14) | 0.0155 (13) |
C11A | 0.0727 (18) | 0.0674 (16) | 0.0514 (14) | −0.0018 (13) | 0.0130 (12) | 0.0269 (12) |
C12A | 0.0606 (15) | 0.0692 (17) | 0.0592 (15) | 0.0112 (13) | 0.0083 (12) | 0.0267 (13) |
C13A | 0.0548 (14) | 0.0513 (13) | 0.0532 (13) | 0.0116 (11) | 0.0147 (11) | 0.0186 (10) |
C14A | 0.095 (2) | 0.081 (2) | 0.0536 (15) | −0.0028 (17) | 0.0060 (15) | 0.0302 (15) |
C15A | 0.117 (3) | 0.092 (2) | 0.0532 (16) | −0.005 (2) | 0.0021 (17) | 0.0273 (16) |
C17A | 0.174 (5) | 0.154 (5) | 0.076 (3) | 0.041 (4) | 0.028 (3) | 0.019 (3) |
C16A | 0.130 (4) | 0.154 (4) | 0.071 (2) | 0.014 (3) | −0.008 (2) | 0.039 (2) |
N1B | 0.0592 (11) | 0.0358 (9) | 0.0488 (10) | 0.0088 (8) | 0.0192 (9) | 0.0160 (8) |
N1A | 0.0471 (10) | 0.0328 (9) | 0.0525 (10) | 0.0058 (7) | 0.0130 (8) | 0.0180 (8) |
N2A | 0.0491 (10) | 0.0340 (9) | 0.0493 (10) | 0.0057 (7) | 0.0127 (8) | 0.0173 (8) |
N2B | 0.0555 (11) | 0.0366 (9) | 0.0461 (9) | 0.0097 (8) | 0.0189 (8) | 0.0171 (8) |
N3B | 0.0512 (11) | 0.0400 (10) | 0.0536 (10) | 0.0098 (8) | 0.0201 (8) | 0.0188 (8) |
N3A | 0.0525 (11) | 0.0343 (9) | 0.0537 (10) | 0.0056 (8) | 0.0151 (8) | 0.0164 (8) |
O1B | 0.0928 (14) | 0.0464 (10) | 0.0925 (14) | 0.0058 (9) | 0.0455 (11) | 0.0293 (9) |
O1A | 0.0766 (12) | 0.0427 (9) | 0.0826 (12) | 0.0184 (8) | 0.0391 (10) | 0.0242 (8) |
O2A | 0.1157 (17) | 0.0349 (9) | 0.1144 (17) | 0.0019 (10) | 0.0567 (14) | 0.0157 (10) |
O2B | 0.0606 (11) | 0.0644 (12) | 0.1115 (16) | 0.0192 (9) | 0.0414 (11) | 0.0334 (11) |
O3A | 0.0955 (16) | 0.1057 (17) | 0.0484 (10) | −0.0107 (13) | 0.0080 (10) | 0.0317 (11) |
O4A | 0.1061 (19) | 0.139 (2) | 0.0681 (14) | −0.0272 (16) | −0.0003 (13) | 0.0480 (15) |
S1A | 0.0540 (3) | 0.0317 (3) | 0.0599 (3) | −0.0010 (2) | 0.0144 (3) | 0.0152 (2) |
S1B | 0.0551 (4) | 0.0462 (3) | 0.0695 (4) | 0.0163 (3) | 0.0258 (3) | 0.0170 (3) |
C14B | 0.076 (3) | 0.140 (5) | 0.077 (3) | 0.007 (3) | 0.012 (3) | 0.016 (3) |
C15B | 0.087 (4) | 0.096 (5) | 0.092 (4) | −0.003 (3) | −0.015 (3) | 0.031 (3) |
C16B | 0.119 (5) | 0.144 (6) | 0.183 (7) | 0.049 (5) | 0.010 (5) | 0.080 (5) |
C17B | 0.143 (7) | 0.097 (4) | 0.082 (4) | −0.004 (5) | 0.015 (4) | 0.010 (3) |
O3B | 0.096 (3) | 0.168 (4) | 0.060 (2) | −0.020 (3) | −0.009 (2) | 0.033 (2) |
O4B | 0.118 (4) | 0.243 (7) | 0.130 (4) | −0.024 (4) | 0.014 (3) | 0.059 (4) |
C14' | 0.104 (7) | 0.121 (7) | 0.085 (6) | −0.012 (6) | −0.005 (6) | 0.055 (6) |
C15' | 0.093 (8) | 0.127 (9) | 0.098 (8) | 0.016 (8) | −0.002 (7) | 0.006 (8) |
C16' | 0.101 (11) | 0.231 (17) | 0.143 (13) | 0.007 (12) | 0.008 (10) | 0.001 (13) |
C17' | 0.135 (15) | 0.140 (13) | 0.107 (13) | −0.017 (12) | −0.009 (11) | 0.027 (11) |
O3B' | 0.114 (8) | 0.175 (8) | 0.086 (6) | −0.052 (7) | −0.019 (6) | 0.036 (6) |
O4B' | 0.122 (9) | 0.242 (14) | 0.130 (10) | 0.053 (9) | 0.005 (8) | 0.071 (9) |
C10B—C11B | 1.375 (5) | C8A—C13A | 1.387 (3) |
C10B—C9B | 1.381 (5) | C8A—C9A | 1.391 (3) |
C10B—H10B | 0.9300 | C9A—C10A | 1.379 (4) |
C11B—C12B | 1.370 (5) | C9A—H9A | 0.9300 |
C11B—O3B | 1.430 (5) | C9B—H9B | 0.9300 |
C11B—O3B' | 1.476 (11) | C10A—C11A | 1.357 (4) |
C12B—C13B | 1.374 (4) | C10A—H10A | 0.9300 |
C12B—H12B | 0.9300 | C11A—C12A | 1.373 (4) |
C13B—C8B | 1.382 (4) | C11A—O3A | 1.401 (3) |
C13B—H13B | 0.9300 | C12A—C13A | 1.381 (3) |
C1B—C2B | 1.491 (3) | C12A—H12A | 0.9300 |
C1B—H1B1 | 0.9600 | C13A—H13A | 0.9300 |
C1B—H1B2 | 0.9600 | C14A—O4A | 1.195 (4) |
C1B—H1B3 | 0.9600 | C14A—O3A | 1.348 (4) |
C1A—C2A | 1.498 (3) | C14A—C15A | 1.507 (4) |
C1A—H1A1 | 0.9600 | C15A—C17A | 1.501 (6) |
C1A—H1A2 | 0.9600 | C15A—C16A | 1.505 (6) |
C1A—H1A3 | 0.9600 | C15A—H15A | 0.9800 |
C2A—O1A | 1.228 (3) | C17A—H17D | 0.9600 |
C2A—N1A | 1.354 (3) | C17A—H17E | 0.9600 |
C2B—O1B | 1.228 (3) | C17A—H17F | 0.9600 |
C2B—N1B | 1.353 (3) | C16A—H16D | 0.9600 |
C3A—N2A | 1.281 (3) | C16A—H16E | 0.9600 |
C3A—N3A | 1.368 (3) | C16A—H16F | 0.9600 |
C3A—S1A | 1.745 (2) | N1B—N2B | 1.402 (2) |
C3B—N2B | 1.278 (3) | N1A—N2A | 1.401 (2) |
C3B—N3B | 1.374 (3) | N3B—H3B | 0.8600 |
C3B—S1B | 1.745 (2) | N3A—H3A | 0.8600 |
C4A—O2A | 1.206 (3) | C14B—O4B | 1.209 (8) |
C4A—N3A | 1.373 (3) | C14B—O3B | 1.266 (7) |
C4A—C5A | 1.487 (4) | C14B—C15B | 1.482 (8) |
C4B—O2B | 1.212 (3) | C15B—C17B | 1.487 (9) |
C4B—N3B | 1.372 (3) | C15B—C16B | 1.511 (9) |
C4B—C5B | 1.495 (4) | C15B—H15B | 0.9800 |
C5A—H5A1 | 0.9600 | C16B—H16A | 0.9600 |
C5A—H5A2 | 0.9600 | C16B—H16B | 0.9600 |
C5A—H5A3 | 0.9600 | C16B—H16C | 0.9600 |
C5B—H5B1 | 0.9600 | C17B—H17A | 0.9600 |
C5B—H5B2 | 0.9600 | C17B—H17B | 0.9600 |
C5B—H5B3 | 0.9600 | C17B—H17C | 0.9600 |
C6B—N1B | 1.487 (3) | C14'—O4B' | 1.212 (15) |
C6B—C8B | 1.514 (3) | C14'—O3B' | 1.256 (14) |
C6B—C7B | 1.527 (3) | C14'—C15' | 1.522 (16) |
C6B—S1B | 1.846 (2) | C15'—C17' | 1.491 (15) |
C6A—N1A | 1.497 (3) | C15'—C16' | 1.544 (16) |
C6A—C7A | 1.524 (3) | C15'—H15' | 0.9800 |
C6A—C8A | 1.529 (3) | C16'—H16G | 0.9600 |
C6A—S1A | 1.850 (2) | C16'—H16H | 0.9600 |
C7A—H7A1 | 0.9600 | C16'—H16I | 0.9600 |
C7A—H7A2 | 0.9600 | C17'—H17G | 0.9600 |
C7A—H7A3 | 0.9600 | C17'—H17H | 0.9600 |
C7B—H7B1 | 0.9600 | C17'—H17I | 0.9600 |
C7B—H7B2 | 0.9600 | O1—H1A | 0.87 (2) |
C7B—H7B3 | 0.9600 | O1—H1B | 0.88 (2) |
C8B—C9B | 1.386 (4) | ||
C11B—C10B—C9B | 118.8 (3) | C9A—C10A—H10A | 119.9 |
C11B—C10B—H10B | 120.6 | C10A—C11A—C12A | 120.8 (2) |
C9B—C10B—H10B | 120.6 | C10A—C11A—O3A | 117.9 (3) |
C12B—C11B—C10B | 121.3 (3) | C12A—C11A—O3A | 121.2 (3) |
C12B—C11B—O3B | 119.4 (4) | C11A—C12A—C13A | 119.1 (3) |
C10B—C11B—O3B | 117.8 (4) | C11A—C12A—H12A | 120.4 |
C12B—C11B—O3B' | 110.3 (7) | C13A—C12A—H12A | 120.4 |
C10B—C11B—O3B' | 122.6 (8) | C12A—C13A—C8A | 121.5 (2) |
C11B—C12B—C13B | 118.9 (3) | C12A—C13A—H13A | 119.3 |
C11B—C12B—H12B | 120.5 | C8A—C13A—H13A | 119.3 |
C13B—C12B—H12B | 120.5 | O4A—C14A—O3A | 122.5 (3) |
C12B—C13B—C8B | 121.5 (3) | O4A—C14A—C15A | 126.2 (3) |
C12B—C13B—H13B | 119.2 | O3A—C14A—C15A | 111.3 (3) |
C8B—C13B—H13B | 119.2 | C17A—C15A—C16A | 112.9 (4) |
C2B—C1B—H1B1 | 109.5 | C17A—C15A—C14A | 109.7 (3) |
C2B—C1B—H1B2 | 109.5 | C16A—C15A—C14A | 110.0 (3) |
H1B1—C1B—H1B2 | 109.5 | C17A—C15A—H15A | 108.0 |
C2B—C1B—H1B3 | 109.5 | C16A—C15A—H15A | 108.0 |
H1B1—C1B—H1B3 | 109.5 | C14A—C15A—H15A | 108.0 |
H1B2—C1B—H1B3 | 109.5 | C15A—C17A—H17D | 109.5 |
C2A—C1A—H1A1 | 109.5 | C15A—C17A—H17E | 109.5 |
C2A—C1A—H1A2 | 109.5 | H17D—C17A—H17E | 109.5 |
H1A1—C1A—H1A2 | 109.5 | C15A—C17A—H17F | 109.5 |
C2A—C1A—H1A3 | 109.5 | H17D—C17A—H17F | 109.5 |
H1A1—C1A—H1A3 | 109.5 | H17E—C17A—H17F | 109.5 |
H1A2—C1A—H1A3 | 109.5 | C15A—C16A—H16D | 109.5 |
O1A—C2A—N1A | 120.2 (2) | C15A—C16A—H16E | 109.5 |
O1A—C2A—C1A | 122.3 (2) | H16D—C16A—H16E | 109.5 |
N1A—C2A—C1A | 117.5 (2) | C15A—C16A—H16F | 109.5 |
O1B—C2B—N1B | 120.3 (2) | H16D—C16A—H16F | 109.5 |
O1B—C2B—C1B | 122.2 (2) | H16E—C16A—H16F | 109.5 |
N1B—C2B—C1B | 117.5 (2) | C2B—N1B—N2B | 119.31 (18) |
N2A—C3A—N3A | 119.36 (19) | C2B—N1B—C6B | 122.96 (18) |
N2A—C3A—S1A | 118.46 (17) | N2B—N1B—C6B | 116.47 (16) |
N3A—C3A—S1A | 122.18 (15) | C2A—N1A—N2A | 119.05 (17) |
N2B—C3B—N3B | 120.21 (19) | C2A—N1A—C6A | 123.88 (18) |
N2B—C3B—S1B | 118.48 (16) | N2A—N1A—C6A | 116.36 (16) |
N3B—C3B—S1B | 121.29 (16) | C3A—N2A—N1A | 110.01 (17) |
O2A—C4A—N3A | 121.3 (2) | C3B—N2B—N1B | 109.86 (17) |
O2A—C4A—C5A | 123.4 (2) | C4B—N3B—C3B | 123.7 (2) |
N3A—C4A—C5A | 115.3 (2) | C4B—N3B—H3B | 118.1 |
O2B—C4B—N3B | 121.1 (2) | C3B—N3B—H3B | 118.1 |
O2B—C4B—C5B | 123.8 (2) | C3A—N3A—C4A | 124.8 (2) |
N3B—C4B—C5B | 115.2 (2) | C3A—N3A—H3A | 117.6 |
C4A—C5A—H5A1 | 109.5 | C4A—N3A—H3A | 117.6 |
C4A—C5A—H5A2 | 109.5 | C14A—O3A—C11A | 119.9 (2) |
H5A1—C5A—H5A2 | 109.5 | C3A—S1A—C6A | 89.58 (10) |
C4A—C5A—H5A3 | 109.5 | C3B—S1B—C6B | 89.29 (10) |
H5A1—C5A—H5A3 | 109.5 | O4B—C14B—O3B | 119.7 (6) |
H5A2—C5A—H5A3 | 109.5 | O4B—C14B—C15B | 122.5 (7) |
C4B—C5B—H5B1 | 109.5 | O3B—C14B—C15B | 116.8 (6) |
C4B—C5B—H5B2 | 109.5 | C14B—C15B—C17B | 115.7 (6) |
H5B1—C5B—H5B2 | 109.5 | C14B—C15B—C16B | 102.7 (6) |
C4B—C5B—H5B3 | 109.5 | C17B—C15B—C16B | 113.7 (7) |
H5B1—C5B—H5B3 | 109.5 | C14B—C15B—H15B | 108.1 |
H5B2—C5B—H5B3 | 109.5 | C17B—C15B—H15B | 108.1 |
N1B—C6B—C8B | 111.11 (18) | C16B—C15B—H15B | 108.1 |
N1B—C6B—C7B | 112.30 (19) | C15B—C16B—H16A | 109.5 |
C8B—C6B—C7B | 114.0 (2) | C15B—C16B—H16B | 109.5 |
N1B—C6B—S1B | 101.72 (14) | H16A—C16B—H16B | 109.5 |
C8B—C6B—S1B | 109.87 (16) | C15B—C16B—H16C | 109.5 |
C7B—C6B—S1B | 107.00 (18) | H16A—C16B—H16C | 109.5 |
N1A—C6A—C7A | 112.66 (18) | H16B—C16B—H16C | 109.5 |
N1A—C6A—C8A | 108.50 (16) | C15B—C17B—H17A | 109.5 |
C7A—C6A—C8A | 114.9 (2) | C15B—C17B—H17B | 109.5 |
N1A—C6A—S1A | 101.53 (14) | H17A—C17B—H17B | 109.5 |
C7A—C6A—S1A | 106.51 (15) | C15B—C17B—H17C | 109.5 |
C8A—C6A—S1A | 111.94 (15) | H17A—C17B—H17C | 109.5 |
C6A—C7A—H7A1 | 109.5 | H17B—C17B—H17C | 109.5 |
C6A—C7A—H7A2 | 109.5 | C14B—O3B—C11B | 115.8 (5) |
H7A1—C7A—H7A2 | 109.5 | O4B'—C14'—O3B' | 117.3 (15) |
C6A—C7A—H7A3 | 109.5 | O4B'—C14'—C15' | 122.0 (15) |
H7A1—C7A—H7A3 | 109.5 | O3B'—C14'—C15' | 120.7 (16) |
H7A2—C7A—H7A3 | 109.5 | C17'—C15'—C14' | 115.4 (17) |
C6B—C7B—H7B1 | 109.5 | C17'—C15'—C16' | 95.1 (17) |
C6B—C7B—H7B2 | 109.5 | C14'—C15'—C16' | 134 (2) |
H7B1—C7B—H7B2 | 109.5 | C17'—C15'—H15' | 102.9 |
C6B—C7B—H7B3 | 109.5 | C14'—C15'—H15' | 102.9 |
H7B1—C7B—H7B3 | 109.5 | C16'—C15'—H15' | 102.9 |
H7B2—C7B—H7B3 | 109.5 | C15'—C16'—H16G | 109.5 |
C13B—C8B—C9B | 118.0 (3) | C15'—C16'—H16H | 109.5 |
C13B—C8B—C6B | 121.6 (2) | H16G—C16'—H16H | 109.5 |
C9B—C8B—C6B | 120.0 (2) | C15'—C16'—H16I | 109.5 |
C13A—C8A—C9A | 117.7 (2) | H16G—C16'—H16I | 109.5 |
C13A—C8A—C6A | 121.2 (2) | H16H—C16'—H16I | 109.5 |
C9A—C8A—C6A | 120.9 (2) | C15'—C17'—H17G | 109.5 |
C10A—C9A—C8A | 120.6 (3) | C15'—C17'—H17H | 109.5 |
C10A—C9A—H9A | 119.7 | H17G—C17'—H17H | 109.5 |
C8A—C9A—H9A | 119.7 | C15'—C17'—H17I | 109.5 |
C10B—C9B—C8B | 121.1 (3) | H17G—C17'—H17I | 109.5 |
C10B—C9B—H9B | 119.5 | H17H—C17'—H17I | 109.5 |
C8B—C9B—H9B | 119.5 | C14'—O3B'—C11B | 111.7 (12) |
C11A—C10A—C9A | 120.3 (3) | H1A—O1—H1B | 105 (3) |
C11A—C10A—H10A | 119.9 | ||
C9B—C10B—C11B—C12B | 4.3 (7) | C7A—C6A—N1A—C2A | −54.8 (3) |
C9B—C10B—C11B—O3B | 170.4 (4) | C8A—C6A—N1A—C2A | 73.6 (2) |
C9B—C10B—C11B—O3B' | −146.4 (7) | S1A—C6A—N1A—C2A | −168.36 (17) |
C10B—C11B—C12B—C13B | −3.3 (7) | C7A—C6A—N1A—N2A | 134.9 (2) |
O3B—C11B—C12B—C13B | −169.1 (4) | C8A—C6A—N1A—N2A | −96.7 (2) |
O3B'—C11B—C12B—C13B | 150.6 (7) | S1A—C6A—N1A—N2A | 21.4 (2) |
C11B—C12B—C13B—C8B | −2.4 (5) | N3A—C3A—N2A—N1A | −177.87 (17) |
C12B—C13B—C8B—C9B | 6.7 (5) | S1A—C3A—N2A—N1A | 1.7 (2) |
C12B—C13B—C8B—C6B | 179.5 (3) | C2A—N1A—N2A—C3A | 172.95 (19) |
N1B—C6B—C8B—C13B | 18.3 (3) | C6A—N1A—N2A—C3A | −16.3 (2) |
C7B—C6B—C8B—C13B | 146.5 (3) | N3B—C3B—N2B—N1B | 178.38 (18) |
S1B—C6B—C8B—C13B | −93.5 (3) | S1B—C3B—N2B—N1B | −0.3 (2) |
N1B—C6B—C8B—C9B | −169.0 (3) | C2B—N1B—N2B—C3B | 177.4 (2) |
C7B—C6B—C8B—C9B | −40.9 (3) | C6B—N1B—N2B—C3B | −15.1 (3) |
S1B—C6B—C8B—C9B | 79.2 (3) | O2B—C4B—N3B—C3B | −5.9 (4) |
N1A—C6A—C8A—C13A | 80.1 (2) | C5B—C4B—N3B—C3B | 173.3 (2) |
C7A—C6A—C8A—C13A | −152.8 (2) | N2B—C3B—N3B—C4B | 171.3 (2) |
S1A—C6A—C8A—C13A | −31.1 (2) | S1B—C3B—N3B—C4B | −10.1 (3) |
N1A—C6A—C8A—C9A | −94.9 (2) | N2A—C3A—N3A—C4A | 177.7 (2) |
C7A—C6A—C8A—C9A | 32.2 (3) | S1A—C3A—N3A—C4A | −1.9 (3) |
S1A—C6A—C8A—C9A | 153.89 (19) | O2A—C4A—N3A—C3A | −4.3 (4) |
C13A—C8A—C9A—C10A | 1.2 (4) | C5A—C4A—N3A—C3A | 174.5 (2) |
C6A—C8A—C9A—C10A | 176.4 (2) | O4A—C14A—O3A—C11A | 2.6 (5) |
C11B—C10B—C9B—C8B | 0.3 (6) | C15A—C14A—O3A—C11A | −178.1 (3) |
C13B—C8B—C9B—C10B | −5.6 (5) | C10A—C11A—O3A—C14A | 121.9 (3) |
C6B—C8B—C9B—C10B | −178.5 (3) | C12A—C11A—O3A—C14A | −62.3 (4) |
C8A—C9A—C10A—C11A | −0.7 (4) | N2A—C3A—S1A—C6A | 9.51 (18) |
C9A—C10A—C11A—C12A | 0.1 (4) | N3A—C3A—S1A—C6A | −170.93 (18) |
C9A—C10A—C11A—O3A | 175.8 (2) | N1A—C6A—S1A—C3A | −15.74 (14) |
C10A—C11A—C12A—C13A | 0.1 (4) | C7A—C6A—S1A—C3A | −133.82 (17) |
O3A—C11A—C12A—C13A | −175.5 (2) | C8A—C6A—S1A—C3A | 99.82 (15) |
C11A—C12A—C13A—C8A | 0.5 (4) | N2B—C3B—S1B—C6B | 11.17 (18) |
C9A—C8A—C13A—C12A | −1.1 (3) | N3B—C3B—S1B—C6B | −167.47 (18) |
C6A—C8A—C13A—C12A | −176.2 (2) | N1B—C6B—S1B—C3B | −16.53 (14) |
O4A—C14A—C15A—C17A | −101.7 (5) | C8B—C6B—S1B—C3B | 101.25 (16) |
O3A—C14A—C15A—C17A | 79.1 (4) | C7B—C6B—S1B—C3B | −134.49 (17) |
O4A—C14A—C15A—C16A | 23.1 (6) | O4B—C14B—C15B—C17B | −139.6 (8) |
O3A—C14A—C15A—C16A | −156.1 (3) | O3B—C14B—C15B—C17B | 29.2 (10) |
O1B—C2B—N1B—N2B | 173.7 (2) | O4B—C14B—C15B—C16B | 95.9 (9) |
C1B—C2B—N1B—N2B | −6.5 (3) | O3B—C14B—C15B—C16B | −95.3 (8) |
O1B—C2B—N1B—C6B | 7.0 (4) | O4B—C14B—O3B—C11B | −6.2 (10) |
C1B—C2B—N1B—C6B | −173.2 (2) | C15B—C14B—O3B—C11B | −175.3 (6) |
C8B—C6B—N1B—C2B | 71.5 (3) | C12B—C11B—O3B—C14B | −88.4 (7) |
C7B—C6B—N1B—C2B | −57.5 (3) | C10B—C11B—O3B—C14B | 105.3 (6) |
S1B—C6B—N1B—C2B | −171.57 (18) | O4B'—C14'—C15'—C17' | 13 (3) |
C8B—C6B—N1B—N2B | −95.5 (2) | O3B'—C14'—C15'—C17' | −167 (2) |
C7B—C6B—N1B—N2B | 135.4 (2) | O4B'—C14'—C15'—C16' | 139 (3) |
S1B—C6B—N1B—N2B | 21.4 (2) | O3B'—C14'—C15'—C16' | −41 (4) |
O1A—C2A—N1A—N2A | 175.0 (2) | O4B'—C14'—O3B'—C11B | 22 (3) |
C1A—C2A—N1A—N2A | −5.1 (3) | C15'—C14'—O3B'—C11B | −158.1 (18) |
O1A—C2A—N1A—C6A | 5.0 (3) | C12B—C11B—O3B'—C14' | 125.5 (14) |
C1A—C2A—N1A—C6A | −175.1 (2) | C10B—C11B—O3B'—C14' | −81.1 (17) |
Cg2 and Cg4 are the centroids of the C8B–C13B and C8A–C13A rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1B···O4Bi | 0.88 (11) | 2.32 (10) | 3.111 (16) | 149 (12) |
N3A—H3A···O1Bii | 0.86 | 1.99 | 2.842 (3) | 171 |
N3B—H3B···O1A | 0.86 | 1.94 | 2.792 (3) | 171 |
C15B—H15B···O1 | 0.98 | 2.46 | 3.368 (19) | 154 |
C7B—H7B2···O1iii | 0.96 | 2.49 | 3.434 (19) | 168 |
C15A—H15A···Cg2iv | 0.98 | 2.99 | 3.959 (4) | 168 |
C17B—H17B···Cg4iv | 0.96 | 2.98 | 3.864 (9) | 153 |
C17′—H17H···Cg4iv | 0.96 | 2.93 | 3.81 (3) | 154 |
Symmetry codes: (i) −x, −y, −z; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y, −z; (iv) −x+1, −y+1, −z. |
C16H19N3O4S | Z = 4 |
Mr = 349.40 | F(000) = 736 |
Triclinic, P1 | Dx = 1.313 Mg m−3 |
a = 11.4150 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.4021 (3) Å | Cell parameters from 7257 reflections |
c = 13.2305 (3) Å | θ = 1.8–26.9° |
α = 71.982 (1)° | µ = 0.21 mm−1 |
β = 89.829 (1)° | T = 293 K |
γ = 83.114 (1)° | Block, colourless |
V = 1767.18 (8) Å3 | 0.25 × 0.24 × 0.20 mm |
Bruker Kappa APEXII CCD diffractometer | 5869 reflections with I > 2σ(I) |
ω and φ scans | Rint = 0.022 |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | θmax = 26.4°, θmin = 1.6° |
Tmin = 0.756, Tmax = 0.824 | h = −14→14 |
26933 measured reflections | k = −15→15 |
7257 independent reflections | l = −16→16 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.106 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0486P)2 + 0.4775P] where P = (Fo2 + 2Fc2)/3 |
7257 reflections | (Δ/σ)max = 0.012 |
451 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.33 e Å−3 |
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 | Occ. (<1) | |
N1A | 0.57800 (12) | 1.34448 (11) | 0.74760 (12) | 0.0525 (3) | |
H1A | 0.620681 | 1.370276 | 0.786145 | 0.063* | |
O1B | 0.30213 (13) | 0.50078 (14) | 0.84275 (14) | 0.0854 (5) | |
O2A | 0.73259 (12) | 0.86411 (11) | 0.91134 (11) | 0.0707 (4) | |
C5A | 0.51016 (19) | 1.54430 (15) | 0.65971 (18) | 0.0696 (5) | |
H5A1 | 0.557477 | 1.576433 | 0.600418 | 0.104* | |
H5A2 | 0.545055 | 1.550089 | 0.723459 | 0.104* | |
H5A3 | 0.432011 | 1.585300 | 0.647905 | 0.104* | |
C5B | 0.41647 (18) | 0.3577 (2) | 0.9822 (2) | 0.0847 (7) | |
H5B1 | 0.440346 | 0.286150 | 0.969805 | 0.127* | |
H5B2 | 0.402035 | 0.344392 | 1.056366 | 0.127* | |
H5B3 | 0.477912 | 0.405929 | 0.961867 | 0.127* | |
C4B | 0.30600 (16) | 0.41497 (16) | 0.91784 (16) | 0.0595 (4) | |
C4A | 0.50385 (16) | 1.42199 (14) | 0.67108 (15) | 0.0545 (4) | |
C3B | 0.09508 (14) | 0.40749 (12) | 0.90740 (12) | 0.0430 (3) | |
C3A | 0.58882 (13) | 1.22853 (13) | 0.76694 (12) | 0.0443 (3) | |
C2B | −0.20340 (15) | 0.38900 (14) | 0.93581 (13) | 0.0475 (4) | |
C2A | 0.74122 (16) | 0.96458 (16) | 0.90086 (14) | 0.0557 (4) | |
C1A | 0.8399 (2) | 1.0004 (2) | 0.95195 (19) | 0.0819 (7) | |
H1A1 | 0.894461 | 0.934423 | 0.987754 | 0.123* | |
H1A2 | 0.808622 | 1.036605 | 1.002461 | 0.123* | |
H1A3 | 0.879963 | 1.053137 | 0.898454 | 0.123* | |
C1B | −0.20176 (18) | 0.30017 (18) | 1.04232 (15) | 0.0661 (5) | |
H1B1 | −0.281171 | 0.286795 | 1.061371 | 0.099* | |
H1B2 | −0.165756 | 0.326230 | 1.094501 | 0.099* | |
H1B3 | −0.157297 | 0.230441 | 1.039480 | 0.099* | |
C6A | 0.56363 (14) | 1.02464 (13) | 0.77881 (13) | 0.0480 (4) | |
C6B | −0.08741 (14) | 0.49848 (13) | 0.78791 (12) | 0.0439 (3) | |
C7B | −0.15459 (18) | 0.61708 (14) | 0.77098 (15) | 0.0599 (5) | |
H7B1 | −0.237776 | 0.613673 | 0.765099 | 0.090* | |
H7B2 | −0.129831 | 0.669363 | 0.706902 | 0.090* | |
H7B3 | −0.138429 | 0.642805 | 0.830298 | 0.090* | |
C7A | 0.46982 (17) | 0.97282 (17) | 0.85428 (16) | 0.0631 (5) | |
H7A1 | 0.498929 | 0.895550 | 0.894576 | 0.095* | |
H7A2 | 0.399801 | 0.973411 | 0.814005 | 0.095* | |
H7A3 | 0.451600 | 1.016824 | 0.901843 | 0.095* | |
C8A | 0.60797 (14) | 0.95904 (13) | 0.70392 (13) | 0.0467 (4) | |
C8B | −0.11842 (13) | 0.44221 (13) | 0.70592 (12) | 0.0427 (3) | |
C13B | −0.11426 (16) | 0.32545 (14) | 0.73185 (13) | 0.0504 (4) | |
H13B | −0.093842 | 0.280152 | 0.801309 | 0.060* | |
C9A | 0.53636 (16) | 0.89412 (15) | 0.66959 (16) | 0.0593 (4) | |
H9A | 0.461151 | 0.886891 | 0.696048 | 0.071* | |
C12B | −0.13966 (17) | 0.27416 (15) | 0.65726 (14) | 0.0555 (4) | |
H12B | −0.136280 | 0.195077 | 0.676341 | 0.067* | |
C10A | 0.57469 (17) | 0.83983 (15) | 0.59663 (16) | 0.0616 (5) | |
H10A | 0.525298 | 0.797237 | 0.573355 | 0.074* | |
C11B | −0.16969 (15) | 0.33979 (16) | 0.55560 (14) | 0.0545 (4) | |
C11A | 0.68586 (16) | 0.84921 (13) | 0.55888 (14) | 0.0520 (4) | |
C10B | −0.1753 (2) | 0.45512 (18) | 0.52740 (16) | 0.0848 (7) | |
H10B | −0.196507 | 0.499665 | 0.457871 | 0.102* | |
C12A | 0.75876 (17) | 0.91397 (17) | 0.59031 (16) | 0.0606 (4) | |
H12A | 0.834058 | 0.920341 | 0.563862 | 0.073* | |
C13A | 0.71888 (16) | 0.96928 (16) | 0.66141 (15) | 0.0588 (4) | |
H13A | 0.767410 | 1.014739 | 0.681596 | 0.071* | |
C9B | −0.1494 (2) | 0.50628 (16) | 0.60244 (15) | 0.0772 (7) | |
H9B | −0.152876 | 0.585410 | 0.582606 | 0.093* | |
C14B | −0.11985 (18) | 0.23156 (17) | 0.43963 (15) | 0.0599 (4) | |
C14A | 0.75675 (15) | 0.84105 (14) | 0.39311 (14) | 0.0518 (4) | |
C15B | −0.1704 (2) | 0.18925 (18) | 0.35733 (16) | 0.0677 (5) | |
H15A | −0.210289 | 0.253823 | 0.301650 | 0.081* | |
H15B | −0.228848 | 0.139518 | 0.389471 | 0.081* | |
C15A | 0.81032 (18) | 0.75962 (16) | 0.33897 (16) | 0.0637 (5) | |
H15C | 0.759433 | 0.700728 | 0.345461 | 0.076* | |
H15D | 0.885816 | 0.722948 | 0.373824 | 0.076* | |
C16A | 0.8284 (2) | 0.8183 (2) | 0.22260 (18) | 0.0888 (7) | |
H16A | 0.753154 | 0.849116 | 0.186584 | 0.133* | |
H16B | 0.867850 | 0.764059 | 0.191567 | 0.133* | |
H16C | 0.875623 | 0.879079 | 0.215732 | 0.133* | |
C16B | −0.0785 (2) | 0.1249 (2) | 0.30835 (19) | 0.0837 (7) | |
H16D | −0.022136 | 0.174521 | 0.273753 | 0.126* | |
H16E | −0.115993 | 0.098469 | 0.257153 | 0.126* | |
H16F | −0.038825 | 0.060581 | 0.362960 | 0.126* | |
N1B | 0.20675 (12) | 0.36478 (12) | 0.95143 (11) | 0.0508 (3) | |
H1B | 0.214485 | 0.302221 | 1.003664 | 0.061* | |
N2B | 0.00570 (12) | 0.36683 (11) | 0.95615 (10) | 0.0462 (3) | |
N2A | 0.66403 (12) | 1.16162 (11) | 0.83704 (11) | 0.0489 (3) | |
N3A | 0.66139 (12) | 1.04853 (11) | 0.83936 (11) | 0.0495 (3) | |
N3B | −0.09860 (11) | 0.42081 (11) | 0.89767 (10) | 0.0440 (3) | |
O1A | 0.43966 (13) | 1.39102 (11) | 0.61613 (12) | 0.0764 (4) | |
O2B | −0.29535 (10) | 0.43215 (11) | 0.88346 (10) | 0.0582 (3) | |
O3A | 0.72748 (12) | 0.78457 (10) | 0.49319 (10) | 0.0604 (3) | |
O3B | −0.20361 (12) | 0.29134 (13) | 0.47883 (11) | 0.0701 (4) | |
O4A | 0.73852 (12) | 0.94268 (10) | 0.35619 (10) | 0.0626 (3) | |
S1B | 0.07220 (4) | 0.51371 (4) | 0.78475 (3) | 0.05286 (12) | |
S1A | 0.50357 (4) | 1.16990 (4) | 0.69416 (4) | 0.05734 (14) | |
O4B | −0.0175 (6) | 0.231 (2) | 0.4588 (16) | 0.081 (3) | 0.68 (6) |
O4B' | −0.030 (3) | 0.184 (4) | 0.491 (3) | 0.081 (7) | 0.32 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0511 (8) | 0.0467 (7) | 0.0612 (8) | −0.0057 (6) | −0.0134 (7) | −0.0190 (6) |
O1B | 0.0618 (9) | 0.0804 (10) | 0.0964 (11) | −0.0195 (7) | 0.0056 (8) | 0.0021 (9) |
O2A | 0.0677 (8) | 0.0523 (7) | 0.0770 (9) | 0.0030 (6) | −0.0193 (7) | −0.0022 (6) |
C5A | 0.0723 (13) | 0.0466 (10) | 0.0855 (14) | −0.0058 (9) | −0.0078 (11) | −0.0147 (9) |
C5B | 0.0452 (11) | 0.0925 (16) | 0.1061 (18) | −0.0056 (10) | −0.0050 (11) | −0.0169 (14) |
C4B | 0.0485 (10) | 0.0601 (11) | 0.0697 (12) | −0.0076 (8) | 0.0031 (9) | −0.0199 (9) |
C4A | 0.0515 (10) | 0.0487 (9) | 0.0608 (10) | −0.0051 (7) | −0.0054 (8) | −0.0140 (8) |
C3B | 0.0461 (9) | 0.0391 (7) | 0.0438 (8) | −0.0035 (6) | −0.0026 (7) | −0.0134 (6) |
C3A | 0.0400 (8) | 0.0479 (8) | 0.0456 (8) | −0.0048 (6) | −0.0033 (7) | −0.0156 (7) |
C2B | 0.0488 (9) | 0.0551 (9) | 0.0449 (8) | −0.0095 (7) | 0.0018 (7) | −0.0236 (7) |
C2A | 0.0506 (10) | 0.0570 (10) | 0.0493 (9) | −0.0006 (8) | −0.0095 (8) | −0.0041 (8) |
C1A | 0.0676 (13) | 0.0804 (14) | 0.0819 (14) | −0.0057 (11) | −0.0356 (11) | −0.0035 (11) |
C1B | 0.0649 (12) | 0.0773 (13) | 0.0548 (10) | −0.0212 (10) | 0.0086 (9) | −0.0141 (9) |
C6A | 0.0451 (9) | 0.0445 (8) | 0.0513 (9) | −0.0009 (7) | −0.0111 (7) | −0.0119 (7) |
C6B | 0.0473 (9) | 0.0409 (8) | 0.0405 (8) | −0.0045 (6) | −0.0030 (7) | −0.0085 (6) |
C7B | 0.0708 (12) | 0.0451 (9) | 0.0607 (11) | 0.0037 (8) | −0.0053 (9) | −0.0161 (8) |
C7A | 0.0535 (10) | 0.0682 (11) | 0.0631 (11) | −0.0028 (9) | −0.0014 (9) | −0.0158 (9) |
C8A | 0.0465 (9) | 0.0371 (7) | 0.0527 (9) | −0.0011 (6) | −0.0079 (7) | −0.0100 (7) |
C8B | 0.0425 (8) | 0.0427 (8) | 0.0402 (8) | −0.0020 (6) | −0.0041 (6) | −0.0105 (6) |
C13B | 0.0623 (10) | 0.0449 (8) | 0.0412 (8) | −0.0051 (7) | 0.0019 (7) | −0.0102 (7) |
C9A | 0.0492 (10) | 0.0549 (10) | 0.0800 (13) | −0.0093 (8) | 0.0005 (9) | −0.0288 (9) |
C12B | 0.0661 (11) | 0.0473 (9) | 0.0572 (10) | −0.0131 (8) | 0.0092 (8) | −0.0198 (8) |
C10A | 0.0603 (11) | 0.0510 (10) | 0.0809 (13) | −0.0124 (8) | −0.0052 (10) | −0.0292 (9) |
C11B | 0.0507 (9) | 0.0642 (10) | 0.0547 (10) | −0.0053 (8) | −0.0077 (8) | −0.0281 (8) |
C11A | 0.0603 (10) | 0.0378 (8) | 0.0555 (9) | 0.0034 (7) | −0.0078 (8) | −0.0147 (7) |
C10B | 0.137 (2) | 0.0612 (12) | 0.0497 (11) | 0.0032 (12) | −0.0350 (12) | −0.0127 (9) |
C12A | 0.0523 (10) | 0.0676 (11) | 0.0669 (11) | −0.0107 (8) | 0.0035 (9) | −0.0269 (9) |
C13A | 0.0569 (10) | 0.0612 (10) | 0.0673 (11) | −0.0190 (8) | 0.0005 (9) | −0.0286 (9) |
C9B | 0.130 (2) | 0.0439 (9) | 0.0515 (10) | −0.0020 (11) | −0.0264 (11) | −0.0090 (8) |
C14B | 0.0666 (12) | 0.0665 (11) | 0.0524 (10) | −0.0142 (10) | −0.0012 (9) | −0.0247 (9) |
C14A | 0.0477 (9) | 0.0474 (9) | 0.0609 (10) | 0.0000 (7) | −0.0114 (8) | −0.0201 (8) |
C15B | 0.0867 (14) | 0.0679 (12) | 0.0568 (11) | −0.0235 (10) | −0.0046 (10) | −0.0265 (9) |
C15A | 0.0602 (11) | 0.0600 (11) | 0.0729 (12) | 0.0093 (9) | −0.0081 (9) | −0.0296 (9) |
C16A | 0.0977 (18) | 0.0957 (17) | 0.0725 (14) | 0.0254 (14) | −0.0056 (12) | −0.0390 (13) |
C16B | 0.1012 (18) | 0.0925 (16) | 0.0759 (14) | −0.0311 (14) | 0.0079 (13) | −0.0458 (13) |
N1B | 0.0448 (7) | 0.0487 (7) | 0.0536 (8) | −0.0030 (6) | −0.0044 (6) | −0.0091 (6) |
N2B | 0.0455 (7) | 0.0470 (7) | 0.0415 (7) | −0.0025 (6) | −0.0039 (6) | −0.0083 (6) |
N2A | 0.0479 (8) | 0.0493 (7) | 0.0483 (7) | −0.0059 (6) | −0.0089 (6) | −0.0136 (6) |
N3A | 0.0488 (8) | 0.0472 (7) | 0.0497 (7) | 0.0006 (6) | −0.0136 (6) | −0.0133 (6) |
N3B | 0.0425 (7) | 0.0482 (7) | 0.0390 (6) | −0.0044 (5) | −0.0033 (5) | −0.0108 (5) |
O1A | 0.0831 (10) | 0.0533 (7) | 0.0862 (10) | −0.0041 (7) | −0.0394 (8) | −0.0135 (7) |
O2B | 0.0444 (6) | 0.0747 (8) | 0.0602 (7) | −0.0063 (6) | −0.0045 (6) | −0.0281 (6) |
O3A | 0.0765 (8) | 0.0419 (6) | 0.0612 (7) | 0.0042 (6) | −0.0027 (6) | −0.0177 (5) |
O3B | 0.0641 (8) | 0.0866 (9) | 0.0729 (9) | −0.0045 (7) | −0.0138 (7) | −0.0458 (8) |
O4A | 0.0758 (9) | 0.0461 (7) | 0.0658 (8) | −0.0045 (6) | −0.0038 (6) | −0.0182 (6) |
S1B | 0.0526 (2) | 0.0518 (2) | 0.0476 (2) | −0.01414 (18) | −0.00393 (18) | −0.00294 (18) |
S1A | 0.0614 (3) | 0.0439 (2) | 0.0653 (3) | 0.00323 (18) | −0.0282 (2) | −0.01838 (19) |
O4B | 0.0605 (18) | 0.116 (7) | 0.089 (5) | −0.015 (3) | 0.001 (2) | −0.064 (5) |
O4B' | 0.075 (7) | 0.105 (13) | 0.078 (8) | 0.010 (8) | −0.011 (6) | −0.058 (9) |
N1A—C4A | 1.369 (2) | C8A—C9A | 1.382 (2) |
N1A—C3A | 1.371 (2) | C8A—C13A | 1.388 (2) |
N1A—H1A | 0.8600 | C8B—C9B | 1.376 (2) |
O1B—C4B | 1.207 (2) | C8B—C13B | 1.376 (2) |
O2A—C2A | 1.226 (2) | C13B—C12B | 1.377 (2) |
C5A—C4A | 1.488 (2) | C13B—H13B | 0.9300 |
C5A—H5A1 | 0.9600 | C9A—C10A | 1.380 (3) |
C5A—H5A2 | 0.9600 | C9A—H9A | 0.9300 |
C5A—H5A3 | 0.9600 | C12B—C11B | 1.359 (2) |
C5B—C4B | 1.496 (3) | C12B—H12B | 0.9300 |
C5B—H5B1 | 0.9600 | C10A—C11A | 1.367 (3) |
C5B—H5B2 | 0.9600 | C10A—H10A | 0.9300 |
C5B—H5B3 | 0.9600 | C11B—C10B | 1.355 (3) |
C4B—N1B | 1.365 (2) | C11B—O3B | 1.406 (2) |
C4A—O1A | 1.207 (2) | C11A—C12A | 1.371 (3) |
C3B—N2B | 1.277 (2) | C11A—O3A | 1.400 (2) |
C3B—N1B | 1.377 (2) | C10B—C9B | 1.383 (3) |
C3B—S1B | 1.7420 (15) | C10B—H10B | 0.9300 |
C3A—N2A | 1.2821 (19) | C12A—C13A | 1.373 (3) |
C3A—S1A | 1.7353 (16) | C12A—H12A | 0.9300 |
C2B—O2B | 1.228 (2) | C13A—H13A | 0.9300 |
C2B—N3B | 1.352 (2) | C9B—H9B | 0.9300 |
C2B—C1B | 1.495 (2) | C14B—O4B | 1.196 (7) |
C2A—N3A | 1.352 (2) | C14B—O4B' | 1.218 (14) |
C2A—C1A | 1.494 (3) | C14B—O3B | 1.341 (2) |
C1A—H1A1 | 0.9600 | C14B—C15B | 1.491 (3) |
C1A—H1A2 | 0.9600 | C14A—O4A | 1.195 (2) |
C1A—H1A3 | 0.9600 | C14A—O3A | 1.355 (2) |
C1B—H1B1 | 0.9600 | C14A—C15A | 1.484 (2) |
C1B—H1B2 | 0.9600 | C15B—C16B | 1.508 (3) |
C1B—H1B3 | 0.9600 | C15B—H15A | 0.9700 |
C6A—N3A | 1.485 (2) | C15B—H15B | 0.9700 |
C6A—C8A | 1.515 (2) | C15A—C16A | 1.511 (3) |
C6A—C7A | 1.523 (3) | C15A—H15C | 0.9700 |
C6A—S1A | 1.8520 (16) | C15A—H15D | 0.9700 |
C6B—N3B | 1.4887 (19) | C16A—H16A | 0.9600 |
C6B—C8B | 1.523 (2) | C16A—H16B | 0.9600 |
C6B—C7B | 1.526 (2) | C16A—H16C | 0.9600 |
C6B—S1B | 1.8531 (16) | C16B—H16D | 0.9600 |
C7B—H7B1 | 0.9600 | C16B—H16E | 0.9600 |
C7B—H7B2 | 0.9600 | C16B—H16F | 0.9600 |
C7B—H7B3 | 0.9600 | N1B—H1B | 0.8600 |
C7A—H7A1 | 0.9600 | N2B—N3B | 1.3993 (17) |
C7A—H7A2 | 0.9600 | N2A—N3A | 1.3973 (19) |
C7A—H7A3 | 0.9600 | ||
C4A—N1A—C3A | 124.42 (14) | C8B—C13B—H13B | 119.3 |
C4A—N1A—H1A | 117.8 | C12B—C13B—H13B | 119.3 |
C3A—N1A—H1A | 117.8 | C10A—C9A—C8A | 121.04 (17) |
C4A—C5A—H5A1 | 109.5 | C10A—C9A—H9A | 119.5 |
C4A—C5A—H5A2 | 109.5 | C8A—C9A—H9A | 119.5 |
H5A1—C5A—H5A2 | 109.5 | C11B—C12B—C13B | 119.62 (16) |
C4A—C5A—H5A3 | 109.5 | C11B—C12B—H12B | 120.2 |
H5A1—C5A—H5A3 | 109.5 | C13B—C12B—H12B | 120.2 |
H5A2—C5A—H5A3 | 109.5 | C11A—C10A—C9A | 119.44 (17) |
C4B—C5B—H5B1 | 109.5 | C11A—C10A—H10A | 120.3 |
C4B—C5B—H5B2 | 109.5 | C9A—C10A—H10A | 120.3 |
H5B1—C5B—H5B2 | 109.5 | C10B—C11B—C12B | 120.48 (16) |
C4B—C5B—H5B3 | 109.5 | C10B—C11B—O3B | 118.06 (16) |
H5B1—C5B—H5B3 | 109.5 | C12B—C11B—O3B | 121.31 (16) |
H5B2—C5B—H5B3 | 109.5 | C10A—C11A—C12A | 121.05 (17) |
O1B—C4B—N1B | 121.23 (17) | C10A—C11A—O3A | 118.62 (16) |
O1B—C4B—C5B | 123.57 (18) | C12A—C11A—O3A | 120.17 (17) |
N1B—C4B—C5B | 115.18 (17) | C11B—C10B—C9B | 119.73 (17) |
O1A—C4A—N1A | 120.96 (16) | C11B—C10B—H10B | 120.1 |
O1A—C4A—C5A | 123.29 (17) | C9B—C10B—H10B | 120.1 |
N1A—C4A—C5A | 115.74 (16) | C11A—C12A—C13A | 118.98 (18) |
N2B—C3B—N1B | 119.51 (14) | C11A—C12A—H12A | 120.5 |
N2B—C3B—S1B | 118.75 (12) | C13A—C12A—H12A | 120.5 |
N1B—C3B—S1B | 121.73 (12) | C12A—C13A—C8A | 121.63 (16) |
N2A—C3A—N1A | 120.77 (14) | C12A—C13A—H13A | 119.2 |
N2A—C3A—S1A | 118.74 (12) | C8A—C13A—H13A | 119.2 |
N1A—C3A—S1A | 120.46 (11) | C8B—C9B—C10B | 121.19 (17) |
O2B—C2B—N3B | 120.27 (15) | C8B—C9B—H9B | 119.4 |
O2B—C2B—C1B | 122.29 (16) | C10B—C9B—H9B | 119.4 |
N3B—C2B—C1B | 117.44 (15) | O4B—C14B—O3B | 120.9 (4) |
O2A—C2A—N3A | 120.37 (16) | O4B'—C14B—O3B | 121.3 (8) |
O2A—C2A—C1A | 122.52 (16) | O4B—C14B—C15B | 126.8 (4) |
N3A—C2A—C1A | 117.10 (17) | O4B'—C14B—C15B | 122.2 (11) |
C2A—C1A—H1A1 | 109.5 | O3B—C14B—C15B | 111.26 (17) |
C2A—C1A—H1A2 | 109.5 | O4A—C14A—O3A | 122.58 (16) |
H1A1—C1A—H1A2 | 109.5 | O4A—C14A—C15A | 126.69 (18) |
C2A—C1A—H1A3 | 109.5 | O3A—C14A—C15A | 110.72 (15) |
H1A1—C1A—H1A3 | 109.5 | C14B—C15B—C16B | 113.05 (19) |
H1A2—C1A—H1A3 | 109.5 | C14B—C15B—H15A | 109.0 |
C2B—C1B—H1B1 | 109.5 | C16B—C15B—H15A | 109.0 |
C2B—C1B—H1B2 | 109.5 | C14B—C15B—H15B | 109.0 |
H1B1—C1B—H1B2 | 109.5 | C16B—C15B—H15B | 109.0 |
C2B—C1B—H1B3 | 109.5 | H15A—C15B—H15B | 107.8 |
H1B1—C1B—H1B3 | 109.5 | C14A—C15A—C16A | 111.95 (17) |
H1B2—C1B—H1B3 | 109.5 | C14A—C15A—H15C | 109.2 |
N3A—C6A—C8A | 112.33 (13) | C16A—C15A—H15C | 109.2 |
N3A—C6A—C7A | 110.08 (14) | C14A—C15A—H15D | 109.2 |
C8A—C6A—C7A | 115.48 (14) | C16A—C15A—H15D | 109.2 |
N3A—C6A—S1A | 102.03 (10) | H15C—C15A—H15D | 107.9 |
C8A—C6A—S1A | 106.50 (11) | C15A—C16A—H16A | 109.5 |
C7A—C6A—S1A | 109.47 (12) | C15A—C16A—H16B | 109.5 |
N3B—C6B—C8B | 110.60 (12) | H16A—C16A—H16B | 109.5 |
N3B—C6B—C7B | 112.08 (13) | C15A—C16A—H16C | 109.5 |
C8B—C6B—C7B | 114.21 (13) | H16A—C16A—H16C | 109.5 |
N3B—C6B—S1B | 102.21 (10) | H16B—C16A—H16C | 109.5 |
C8B—C6B—S1B | 109.71 (11) | C15B—C16B—H16D | 109.5 |
C7B—C6B—S1B | 107.27 (12) | C15B—C16B—H16E | 109.5 |
C6B—C7B—H7B1 | 109.5 | H16D—C16B—H16E | 109.5 |
C6B—C7B—H7B2 | 109.5 | C15B—C16B—H16F | 109.5 |
H7B1—C7B—H7B2 | 109.5 | H16D—C16B—H16F | 109.5 |
C6B—C7B—H7B3 | 109.5 | H16E—C16B—H16F | 109.5 |
H7B1—C7B—H7B3 | 109.5 | C4B—N1B—C3B | 124.47 (15) |
H7B2—C7B—H7B3 | 109.5 | C4B—N1B—H1B | 117.8 |
C6A—C7A—H7A1 | 109.5 | C3B—N1B—H1B | 117.8 |
C6A—C7A—H7A2 | 109.5 | C3B—N2B—N3B | 110.39 (12) |
H7A1—C7A—H7A2 | 109.5 | C3A—N2A—N3A | 110.07 (13) |
C6A—C7A—H7A3 | 109.5 | C2A—N3A—N2A | 120.02 (14) |
H7A1—C7A—H7A3 | 109.5 | C2A—N3A—C6A | 122.34 (14) |
H7A2—C7A—H7A3 | 109.5 | N2A—N3A—C6A | 117.49 (12) |
C9A—C8A—C13A | 117.81 (16) | C2B—N3B—N2B | 119.44 (13) |
C9A—C8A—C6A | 121.21 (15) | C2B—N3B—C6B | 122.35 (13) |
C13A—C8A—C6A | 120.81 (15) | N2B—N3B—C6B | 117.53 (12) |
C9B—C8B—C13B | 117.51 (15) | C14A—O3A—C11A | 118.09 (13) |
C9B—C8B—C6B | 121.12 (14) | C14B—O3B—C11B | 118.32 (15) |
C13B—C8B—C6B | 121.36 (13) | C3B—S1B—C6B | 89.96 (7) |
C8B—C13B—C12B | 121.48 (15) | C3A—S1A—C6A | 89.90 (7) |
C3A—N1A—C4A—O1A | 1.8 (3) | S1B—C3B—N2B—N3B | −0.89 (18) |
C3A—N1A—C4A—C5A | −177.04 (17) | N1A—C3A—N2A—N3A | −177.85 (14) |
C4A—N1A—C3A—N2A | 176.96 (17) | S1A—C3A—N2A—N3A | 0.39 (19) |
C4A—N1A—C3A—S1A | −1.2 (2) | O2A—C2A—N3A—N2A | 172.94 (16) |
N3A—C6A—C8A—C9A | 156.77 (15) | C1A—C2A—N3A—N2A | −8.5 (3) |
C7A—C6A—C8A—C9A | 29.4 (2) | O2A—C2A—N3A—C6A | −2.5 (3) |
S1A—C6A—C8A—C9A | −92.34 (16) | C1A—C2A—N3A—C6A | 176.07 (18) |
N3A—C6A—C8A—C13A | −28.1 (2) | C3A—N2A—N3A—C2A | 173.99 (16) |
C7A—C6A—C8A—C13A | −155.50 (16) | C3A—N2A—N3A—C6A | −10.4 (2) |
S1A—C6A—C8A—C13A | 82.75 (16) | C8A—C6A—N3A—C2A | −56.7 (2) |
N3B—C6B—C8B—C9B | 160.12 (18) | C7A—C6A—N3A—C2A | 73.5 (2) |
C7B—C6B—C8B—C9B | 32.6 (2) | S1A—C6A—N3A—C2A | −170.36 (14) |
S1B—C6B—C8B—C9B | −87.87 (19) | C8A—C6A—N3A—N2A | 127.76 (14) |
N3B—C6B—C8B—C13B | −21.2 (2) | C7A—C6A—N3A—N2A | −102.04 (16) |
C7B—C6B—C8B—C13B | −148.76 (16) | S1A—C6A—N3A—N2A | 14.10 (17) |
S1B—C6B—C8B—C13B | 90.79 (16) | O2B—C2B—N3B—N2B | −176.98 (14) |
C9B—C8B—C13B—C12B | 0.2 (3) | C1B—C2B—N3B—N2B | 2.7 (2) |
C6B—C8B—C13B—C12B | −178.50 (16) | O2B—C2B—N3B—C6B | −6.7 (2) |
C13A—C8A—C9A—C10A | 1.0 (3) | C1B—C2B—N3B—C6B | 172.99 (15) |
C6A—C8A—C9A—C10A | 176.22 (16) | C3B—N2B—N3B—C2B | 179.54 (14) |
C8B—C13B—C12B—C11B | −0.1 (3) | C3B—N2B—N3B—C6B | 8.79 (19) |
C8A—C9A—C10A—C11A | 0.9 (3) | C8B—C6B—N3B—C2B | −65.22 (18) |
C13B—C12B—C11B—C10B | −0.3 (3) | C7B—C6B—N3B—C2B | 63.48 (19) |
C13B—C12B—C11B—O3B | −175.85 (17) | S1B—C6B—N3B—C2B | 178.04 (12) |
C9A—C10A—C11A—C12A | −1.6 (3) | C8B—C6B—N3B—N2B | 105.25 (15) |
C9A—C10A—C11A—O3A | 173.75 (16) | C7B—C6B—N3B—N2B | −126.05 (15) |
C12B—C11B—C10B—C9B | 0.5 (4) | S1B—C6B—N3B—N2B | −11.50 (15) |
O3B—C11B—C10B—C9B | 176.2 (2) | O4A—C14A—O3A—C11A | −6.9 (2) |
C10A—C11A—C12A—C13A | 0.5 (3) | C15A—C14A—O3A—C11A | 174.20 (15) |
O3A—C11A—C12A—C13A | −174.87 (16) | C10A—C11A—O3A—C14A | 119.16 (18) |
C11A—C12A—C13A—C8A | 1.5 (3) | C12A—C11A—O3A—C14A | −65.4 (2) |
C9A—C8A—C13A—C12A | −2.2 (3) | O4B—C14B—O3B—C11B | −9.4 (16) |
C6A—C8A—C13A—C12A | −177.47 (16) | O4B'—C14B—O3B—C11B | 27 (3) |
C13B—C8B—C9B—C10B | 0.0 (3) | C15B—C14B—O3B—C11B | −178.40 (16) |
C6B—C8B—C9B—C10B | 178.7 (2) | C10B—C11B—O3B—C14B | 110.6 (2) |
C11B—C10B—C9B—C8B | −0.4 (4) | C12B—C11B—O3B—C14B | −73.7 (2) |
O4B—C14B—C15B—C16B | 9.9 (17) | N2B—C3B—S1B—C6B | −5.09 (13) |
O4B'—C14B—C15B—C16B | −27 (3) | N1B—C3B—S1B—C6B | 173.34 (14) |
O3B—C14B—C15B—C16B | 178.04 (18) | N3B—C6B—S1B—C3B | 8.44 (10) |
O4A—C14A—C15A—C16A | −6.8 (3) | C8B—C6B—S1B—C3B | −108.95 (11) |
O3A—C14A—C15A—C16A | 172.10 (18) | C7B—C6B—S1B—C3B | 126.48 (12) |
O1B—C4B—N1B—C3B | −2.5 (3) | N2A—C3A—S1A—C6A | 6.85 (15) |
C5B—C4B—N1B—C3B | 175.98 (18) | N1A—C3A—S1A—C6A | −174.91 (14) |
N2B—C3B—N1B—C4B | −167.01 (16) | N3A—C6A—S1A—C3A | −10.64 (11) |
S1B—C3B—N1B—C4B | 14.6 (2) | C8A—C6A—S1A—C3A | −128.55 (11) |
N1B—C3B—N2B—N3B | −179.36 (13) | C7A—C6A—S1A—C3A | 105.95 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1A···O2Bi | 0.86 | 1.99 | 2.8469 (19) | 174 |
N1B—H1B···O2Aii | 0.86 | 2.04 | 2.860 (2) | 160 |
C9B—H9B···O3Aiii | 0.93 | 2.60 | 3.426 (2) | 148 |
Symmetry codes: (i) x+1, y+1, z; (ii) −x+1, −y+1, −z+2; (iii) x−1, y, z. |
C22H21N3O4S·0.5CHCl3 | Z = 4 |
Mr = 483.16 | F(000) = 1004 |
Triclinic, P1 | Dx = 1.350 Mg m−3 |
a = 10.7427 (1) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.0828 (2) Å | Cell parameters from 8335 reflections |
c = 20.8969 (3) Å | θ = 1.8–26.9° |
α = 93.186 (1)° | µ = 0.34 mm−1 |
β = 103.945 (4)° | T = 293 K |
γ = 98.489 (2)° | Block, colourless |
V = 2377.39 (7) Å3 | 0.30 × 0.25 × 0.20 mm |
Bruker Kappa APEXII CCD diffractometer | 6495 reflections with I > 2σ(I) |
ω and φ scans | Rint = 0.027 |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | θmax = 25.0°, θmin = 1.9° |
Tmin = 0.741, Tmax = 0.856 | h = −12→12 |
31719 measured reflections | k = −13→13 |
8335 independent reflections | l = −24→24 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.058 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.195 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.1202P)2 + 0.801P] where P = (Fo2 + 2Fc2)/3 |
8335 reflections | (Δ/σ)max = 0.001 |
583 parameters | Δρmax = 0.54 e Å−3 |
0 restraints | Δρmin = −0.60 e Å−3 |
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 | ||
C1A | 0.7194 (4) | 0.1544 (3) | 0.06419 (17) | 0.0762 (10) | |
H1A1 | 0.679416 | 0.205916 | 0.032712 | 0.114* | |
H1A2 | 0.656947 | 0.117324 | 0.086277 | 0.114* | |
H1A3 | 0.749989 | 0.091555 | 0.041580 | 0.114* | |
C1B | 0.6139 (3) | 0.7996 (3) | 0.05275 (15) | 0.0639 (8) | |
H1B1 | 0.695480 | 0.854537 | 0.064442 | 0.096* | |
H1B2 | 0.544321 | 0.845480 | 0.051555 | 0.096* | |
H1B3 | 0.602589 | 0.757019 | 0.009951 | 0.096* | |
C2A | 0.8309 (3) | 0.2293 (3) | 0.11376 (14) | 0.0533 (7) | |
C2B | 0.6126 (3) | 0.7094 (2) | 0.10287 (13) | 0.0484 (6) | |
C3A | 0.9511 (2) | 0.0017 (2) | 0.20325 (12) | 0.0428 (5) | |
C3B | 0.3223 (2) | 0.5173 (2) | 0.03235 (12) | 0.0427 (5) | |
C4A | 1.0210 (3) | −0.1768 (3) | 0.25439 (14) | 0.0513 (6) | |
C4B | 0.1169 (3) | 0.3955 (3) | −0.02802 (15) | 0.0583 (7) | |
C5A | 0.9753 (3) | −0.3054 (3) | 0.26544 (17) | 0.0680 (8) | |
H5A1 | 1.045685 | −0.351101 | 0.269622 | 0.102* | |
H5A2 | 0.905121 | −0.341904 | 0.228557 | 0.102* | |
H5A3 | 0.945710 | −0.306228 | 0.305263 | 0.102* | |
C5B | 0.0036 (3) | 0.3916 (4) | −0.08641 (18) | 0.0799 (10) | |
H5B1 | −0.051581 | 0.313263 | −0.092202 | 0.120* | |
H5B2 | 0.034438 | 0.403920 | −0.125414 | 0.120* | |
H5B3 | −0.044694 | 0.455046 | −0.079113 | 0.120* | |
C6A | 1.0106 (2) | 0.2332 (2) | 0.21533 (13) | 0.0465 (6) | |
C6B | 0.4970 (2) | 0.5235 (2) | 0.13959 (12) | 0.0432 (5) | |
C7A | 1.1137 (3) | 0.3185 (3) | 0.19223 (17) | 0.0632 (8) | |
H7A1 | 1.128809 | 0.280281 | 0.153057 | 0.095* | |
H7A2 | 1.193202 | 0.334094 | 0.226558 | 0.095* | |
H7A3 | 1.083562 | 0.394438 | 0.182604 | 0.095* | |
C7B | 0.6069 (3) | 0.4474 (3) | 0.14865 (15) | 0.0574 (7) | |
H7B1 | 0.611552 | 0.413704 | 0.106132 | 0.086* | |
H7B2 | 0.590135 | 0.382120 | 0.175304 | 0.086* | |
H7B3 | 0.687998 | 0.498827 | 0.170196 | 0.086* | |
C8A | 0.9573 (2) | 0.2918 (2) | 0.26755 (13) | 0.0439 (6) | |
C8B | 0.4791 (2) | 0.5838 (2) | 0.20332 (12) | 0.0430 (5) | |
C9A | 0.8302 (3) | 0.2560 (3) | 0.27116 (15) | 0.0579 (7) | |
H9A | 0.774920 | 0.197301 | 0.239339 | 0.069* | |
C9B | 0.5678 (3) | 0.5896 (3) | 0.26339 (14) | 0.0604 (7) | |
H9B | 0.642341 | 0.554829 | 0.266019 | 0.072* | |
C10A | 0.7844 (3) | 0.3056 (3) | 0.32095 (16) | 0.0636 (8) | |
H10A | 0.698835 | 0.280633 | 0.322681 | 0.076* | |
C10B | 0.5487 (3) | 0.6453 (3) | 0.31927 (15) | 0.0672 (8) | |
H10B | 0.609121 | 0.646886 | 0.359678 | 0.081* | |
C11A | 0.8654 (3) | 0.3919 (3) | 0.36804 (14) | 0.0549 (7) | |
C11B | 0.4411 (3) | 0.6985 (3) | 0.31586 (14) | 0.0543 (7) | |
C12A | 0.9920 (3) | 0.4299 (3) | 0.36570 (15) | 0.0574 (7) | |
H12A | 1.046685 | 0.488670 | 0.397663 | 0.069* | |
C12B | 0.3529 (3) | 0.6951 (4) | 0.25795 (16) | 0.0733 (9) | |
H12B | 0.279542 | 0.731560 | 0.255771 | 0.088* | |
C13A | 1.0363 (3) | 0.3802 (3) | 0.31574 (14) | 0.0530 (7) | |
H13A | 1.121732 | 0.406325 | 0.314039 | 0.064* | |
C13B | 0.3712 (3) | 0.6372 (4) | 0.20168 (15) | 0.0702 (9) | |
H13B | 0.309114 | 0.634359 | 0.161743 | 0.084* | |
C14A | 0.8162 (3) | 0.5525 (3) | 0.43336 (15) | 0.0570 (7) | |
C14B | 0.3303 (3) | 0.7229 (3) | 0.39933 (14) | 0.0551 (7) | |
C15A | 0.7524 (3) | 0.5734 (3) | 0.48581 (14) | 0.0606 (7) | |
H15A | 0.722788 | 0.507454 | 0.506914 | 0.073* | |
C15B | 0.3246 (3) | 0.8066 (3) | 0.45431 (14) | 0.0590 (7) | |
H15B | 0.395847 | 0.867181 | 0.473069 | 0.071* | |
C16A | 0.7357 (3) | 0.6851 (3) | 0.50409 (14) | 0.0582 (7) | |
H16A | 0.767123 | 0.747609 | 0.481341 | 0.070* | |
C16B | 0.2218 (3) | 0.7990 (3) | 0.47811 (14) | 0.0563 (7) | |
H16B | 0.154112 | 0.735313 | 0.458827 | 0.068* | |
C17A | 0.6744 (3) | 0.7222 (3) | 0.55536 (14) | 0.0571 (7) | |
C17B | 0.2007 (3) | 0.8783 (3) | 0.53116 (13) | 0.0527 (6) | |
C18A | 0.6129 (4) | 0.6396 (3) | 0.5895 (2) | 0.0805 (10) | |
H18A | 0.607888 | 0.556028 | 0.579260 | 0.097* | |
C18B | 0.0791 (3) | 0.8648 (4) | 0.54331 (18) | 0.0796 (10) | |
H18B | 0.012376 | 0.805620 | 0.517842 | 0.096* | |
C19A | 0.5588 (4) | 0.6798 (4) | 0.6385 (2) | 0.0973 (13) | |
H19A | 0.516647 | 0.623096 | 0.660692 | 0.117* | |
C19B | 0.0559 (4) | 0.9382 (5) | 0.5928 (2) | 0.1002 (14) | |
H19B | −0.026287 | 0.927828 | 0.600861 | 0.120* | |
C20A | 0.5667 (4) | 0.8028 (4) | 0.6549 (2) | 0.0883 (12) | |
H20A | 0.530013 | 0.829440 | 0.687996 | 0.106* | |
C20B | 0.1510 (5) | 1.0252 (4) | 0.6299 (2) | 0.0951 (13) | |
H20B | 0.133699 | 1.075734 | 0.662592 | 0.114* | |
C21A | 0.6284 (3) | 0.8853 (4) | 0.62237 (18) | 0.0754 (10) | |
H21A | 0.634720 | 0.968781 | 0.633653 | 0.090* | |
C21B | 0.2717 (5) | 1.0388 (4) | 0.61940 (19) | 0.0928 (13) | |
H21B | 0.337669 | 1.098062 | 0.645371 | 0.111* | |
C22A | 0.6817 (3) | 0.8462 (3) | 0.57277 (16) | 0.0656 (8) | |
H22A | 0.723142 | 0.903687 | 0.550683 | 0.079* | |
C22B | 0.2968 (3) | 0.9659 (3) | 0.57086 (16) | 0.0704 (9) | |
H22B | 0.380255 | 0.975483 | 0.564433 | 0.085* | |
C24 | 1.3645 (7) | 0.9979 (5) | 0.1756 (3) | 0.1254 (18) | |
H24 | 1.320200 | 0.999896 | 0.211398 | 0.150* | |
N1A | 0.9043 (2) | 0.1694 (2) | 0.15926 (10) | 0.0479 (5) | |
N1B | 0.5106 (2) | 0.61660 (19) | 0.09130 (10) | 0.0433 (5) | |
N2A | 0.9315 (2) | −0.1208 (2) | 0.21358 (11) | 0.0470 (5) | |
H2A | 0.858413 | −0.164752 | 0.193076 | 0.056* | |
N2B | 0.2116 (2) | 0.4957 (2) | −0.01916 (11) | 0.0502 (5) | |
H2B | 0.201657 | 0.548981 | −0.047555 | 0.060* | |
N3A | 0.8666 (2) | 0.04364 (19) | 0.16030 (11) | 0.0469 (5) | |
N3B | 0.4087 (2) | 0.61029 (19) | 0.03472 (10) | 0.0445 (5) | |
O1A | 0.8567 (2) | 0.34125 (19) | 0.11497 (11) | 0.0623 (5) | |
O1B | 0.70071 (19) | 0.7159 (2) | 0.15333 (10) | 0.0637 (5) | |
O2A | 1.1291 (2) | −0.1226 (2) | 0.28060 (13) | 0.0768 (7) | |
O2B | 0.1249 (3) | 0.3165 (2) | 0.00948 (13) | 0.0913 (8) | |
O3A | 0.8151 (2) | 0.4318 (2) | 0.42002 (11) | 0.0691 (6) | |
O3B | 0.4300 (2) | 0.7646 (2) | 0.37297 (10) | 0.0688 (6) | |
O4A | 0.8612 (3) | 0.6288 (2) | 0.40394 (13) | 0.0848 (8) | |
O4B | 0.2575 (2) | 0.6284 (2) | 0.37835 (12) | 0.0732 (6) | |
Cl1 | 1.5222 (2) | 0.9672 (2) | 0.20900 (13) | 0.1808 (8) | |
Cl2 | 1.2776 (3) | 0.8889 (2) | 0.11689 (11) | 0.2206 (13) | |
Cl3 | 1.3765 (3) | 1.14052 (19) | 0.14707 (17) | 0.2181 (12) | |
S1A | 1.08765 (6) | 0.10243 (6) | 0.24908 (4) | 0.0508 (2) | |
S1B | 0.34553 (7) | 0.42085 (6) | 0.09567 (3) | 0.0545 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1A | 0.082 (2) | 0.065 (2) | 0.067 (2) | 0.0200 (17) | −0.0145 (17) | 0.0092 (16) |
C1B | 0.0673 (18) | 0.0550 (17) | 0.0610 (17) | −0.0091 (14) | 0.0098 (14) | 0.0149 (14) |
C2A | 0.0551 (15) | 0.0531 (17) | 0.0535 (15) | 0.0188 (13) | 0.0101 (13) | 0.0093 (12) |
C2B | 0.0463 (14) | 0.0460 (14) | 0.0510 (15) | 0.0035 (11) | 0.0110 (12) | 0.0059 (11) |
C3A | 0.0395 (12) | 0.0463 (14) | 0.0437 (13) | 0.0122 (10) | 0.0097 (10) | 0.0046 (11) |
C3B | 0.0470 (13) | 0.0409 (13) | 0.0413 (13) | 0.0067 (11) | 0.0136 (10) | 0.0038 (10) |
C4A | 0.0485 (15) | 0.0518 (15) | 0.0544 (15) | 0.0179 (12) | 0.0084 (12) | 0.0055 (12) |
C4B | 0.0587 (16) | 0.0536 (17) | 0.0563 (16) | −0.0040 (13) | 0.0114 (13) | 0.0007 (14) |
C5A | 0.0688 (19) | 0.0624 (19) | 0.071 (2) | 0.0157 (15) | 0.0074 (16) | 0.0210 (15) |
C5B | 0.068 (2) | 0.076 (2) | 0.075 (2) | −0.0125 (17) | −0.0051 (17) | −0.0012 (18) |
C6A | 0.0375 (12) | 0.0462 (14) | 0.0553 (15) | 0.0080 (10) | 0.0090 (11) | 0.0094 (11) |
C6B | 0.0468 (13) | 0.0433 (13) | 0.0422 (13) | 0.0083 (10) | 0.0143 (10) | 0.0106 (10) |
C7A | 0.0517 (16) | 0.0670 (19) | 0.0725 (19) | 0.0017 (14) | 0.0215 (14) | 0.0158 (15) |
C7B | 0.0640 (17) | 0.0566 (17) | 0.0588 (16) | 0.0224 (14) | 0.0210 (14) | 0.0104 (13) |
C8A | 0.0391 (12) | 0.0391 (13) | 0.0522 (14) | 0.0072 (10) | 0.0072 (11) | 0.0106 (11) |
C8B | 0.0404 (12) | 0.0481 (14) | 0.0416 (13) | 0.0088 (10) | 0.0104 (10) | 0.0097 (10) |
C9A | 0.0432 (14) | 0.0574 (17) | 0.0686 (18) | −0.0024 (12) | 0.0151 (13) | −0.0080 (14) |
C9B | 0.0535 (16) | 0.079 (2) | 0.0504 (16) | 0.0248 (14) | 0.0077 (13) | 0.0047 (14) |
C10A | 0.0484 (15) | 0.0632 (19) | 0.080 (2) | 0.0017 (13) | 0.0239 (15) | −0.0034 (16) |
C10B | 0.0640 (18) | 0.089 (2) | 0.0446 (15) | 0.0199 (16) | 0.0038 (13) | −0.0036 (15) |
C11A | 0.0644 (17) | 0.0493 (15) | 0.0547 (16) | 0.0140 (13) | 0.0188 (13) | 0.0063 (12) |
C11B | 0.0523 (15) | 0.0601 (17) | 0.0498 (15) | −0.0003 (13) | 0.0195 (12) | −0.0050 (13) |
C12A | 0.0552 (16) | 0.0505 (16) | 0.0596 (17) | 0.0053 (13) | 0.0051 (13) | −0.0037 (13) |
C12B | 0.0629 (18) | 0.103 (3) | 0.0615 (18) | 0.0410 (18) | 0.0159 (15) | −0.0015 (18) |
C13A | 0.0397 (13) | 0.0475 (15) | 0.0659 (17) | 0.0024 (11) | 0.0054 (12) | 0.0017 (13) |
C13B | 0.0597 (18) | 0.106 (3) | 0.0482 (16) | 0.0386 (18) | 0.0066 (14) | 0.0016 (16) |
C14A | 0.0629 (17) | 0.0595 (18) | 0.0515 (15) | 0.0194 (14) | 0.0134 (13) | 0.0090 (14) |
C14B | 0.0583 (16) | 0.0581 (17) | 0.0510 (15) | 0.0077 (14) | 0.0195 (13) | 0.0038 (13) |
C15A | 0.0626 (17) | 0.070 (2) | 0.0518 (16) | 0.0162 (15) | 0.0148 (14) | 0.0086 (14) |
C15B | 0.0604 (17) | 0.0621 (18) | 0.0525 (16) | 0.0006 (14) | 0.0185 (13) | −0.0034 (13) |
C16A | 0.0579 (16) | 0.0639 (18) | 0.0537 (16) | 0.0156 (14) | 0.0118 (13) | 0.0082 (13) |
C16B | 0.0610 (17) | 0.0563 (17) | 0.0521 (15) | 0.0044 (13) | 0.0188 (13) | 0.0036 (13) |
C17A | 0.0501 (15) | 0.0641 (18) | 0.0551 (16) | 0.0129 (13) | 0.0084 (12) | 0.0005 (14) |
C17B | 0.0589 (16) | 0.0563 (16) | 0.0472 (14) | 0.0114 (13) | 0.0196 (12) | 0.0082 (12) |
C18A | 0.087 (2) | 0.065 (2) | 0.100 (3) | 0.0131 (18) | 0.046 (2) | −0.0006 (19) |
C18B | 0.0610 (19) | 0.103 (3) | 0.076 (2) | 0.0076 (18) | 0.0262 (17) | −0.005 (2) |
C19A | 0.104 (3) | 0.091 (3) | 0.115 (3) | 0.009 (2) | 0.066 (3) | 0.008 (2) |
C19B | 0.079 (3) | 0.144 (4) | 0.093 (3) | 0.034 (3) | 0.046 (2) | 0.001 (3) |
C20A | 0.078 (2) | 0.098 (3) | 0.093 (3) | 0.008 (2) | 0.038 (2) | −0.020 (2) |
C20B | 0.126 (4) | 0.099 (3) | 0.074 (2) | 0.031 (3) | 0.047 (3) | −0.009 (2) |
C21A | 0.0651 (19) | 0.074 (2) | 0.080 (2) | 0.0074 (17) | 0.0121 (17) | −0.0206 (18) |
C21B | 0.116 (3) | 0.087 (3) | 0.069 (2) | −0.013 (2) | 0.035 (2) | −0.017 (2) |
C22A | 0.0594 (17) | 0.069 (2) | 0.0665 (19) | 0.0123 (15) | 0.0124 (15) | 0.0028 (15) |
C22B | 0.0693 (19) | 0.078 (2) | 0.0634 (19) | −0.0020 (16) | 0.0272 (16) | −0.0027 (16) |
C24 | 0.168 (5) | 0.093 (3) | 0.119 (4) | 0.023 (3) | 0.043 (4) | 0.006 (3) |
N1A | 0.0458 (11) | 0.0486 (12) | 0.0466 (12) | 0.0108 (9) | 0.0037 (9) | 0.0088 (9) |
N1B | 0.0444 (11) | 0.0436 (11) | 0.0404 (11) | 0.0034 (9) | 0.0091 (9) | 0.0086 (9) |
N2A | 0.0415 (11) | 0.0471 (12) | 0.0500 (12) | 0.0090 (9) | 0.0055 (9) | 0.0059 (9) |
N2B | 0.0505 (12) | 0.0498 (13) | 0.0457 (12) | 0.0005 (10) | 0.0067 (10) | 0.0097 (10) |
N3A | 0.0456 (11) | 0.0440 (12) | 0.0479 (12) | 0.0093 (9) | 0.0045 (9) | 0.0055 (9) |
N3B | 0.0440 (11) | 0.0464 (12) | 0.0399 (11) | 0.0032 (9) | 0.0065 (9) | 0.0059 (9) |
O1A | 0.0632 (12) | 0.0530 (12) | 0.0688 (13) | 0.0158 (9) | 0.0061 (10) | 0.0190 (10) |
O1B | 0.0515 (11) | 0.0662 (13) | 0.0604 (12) | −0.0058 (9) | −0.0027 (9) | 0.0112 (10) |
O2A | 0.0540 (12) | 0.0581 (13) | 0.1058 (18) | 0.0173 (10) | −0.0092 (12) | 0.0100 (12) |
O2B | 0.0909 (18) | 0.0728 (16) | 0.0852 (17) | −0.0283 (13) | −0.0044 (14) | 0.0229 (14) |
O3A | 0.0904 (16) | 0.0576 (13) | 0.0693 (13) | 0.0136 (11) | 0.0388 (12) | 0.0051 (10) |
O3B | 0.0651 (12) | 0.0771 (15) | 0.0625 (12) | −0.0080 (11) | 0.0302 (10) | −0.0173 (11) |
O4A | 0.121 (2) | 0.0660 (15) | 0.0900 (17) | 0.0323 (14) | 0.0583 (16) | 0.0181 (13) |
O4B | 0.0861 (15) | 0.0571 (13) | 0.0781 (15) | −0.0089 (12) | 0.0397 (12) | −0.0078 (11) |
Cl1 | 0.1491 (16) | 0.1571 (16) | 0.220 (2) | 0.0242 (13) | 0.0127 (15) | 0.0345 (15) |
Cl2 | 0.292 (3) | 0.1581 (18) | 0.1448 (16) | 0.0026 (19) | −0.0530 (18) | 0.0216 (13) |
Cl3 | 0.261 (3) | 0.1176 (13) | 0.342 (3) | 0.0661 (16) | 0.164 (3) | 0.1005 (18) |
S1A | 0.0372 (3) | 0.0504 (4) | 0.0610 (4) | 0.0115 (3) | 0.0027 (3) | 0.0053 (3) |
S1B | 0.0620 (4) | 0.0483 (4) | 0.0473 (4) | −0.0053 (3) | 0.0097 (3) | 0.0128 (3) |
C1A—C2A | 1.487 (4) | C10B—H10B | 0.9300 |
C1A—H1A1 | 0.9600 | C11A—C12A | 1.376 (4) |
C1A—H1A2 | 0.9600 | C11A—O3A | 1.403 (3) |
C1A—H1A3 | 0.9600 | C11B—C12B | 1.340 (4) |
C1B—C2B | 1.489 (4) | C11B—O3B | 1.404 (3) |
C1B—H1B1 | 0.9600 | C12A—C13A | 1.369 (4) |
C1B—H1B2 | 0.9600 | C12A—H12A | 0.9300 |
C1B—H1B3 | 0.9600 | C12B—C13B | 1.377 (4) |
C2A—O1A | 1.228 (3) | C12B—H12B | 0.9300 |
C2A—N1A | 1.353 (3) | C13A—H13A | 0.9300 |
C2B—O1B | 1.226 (3) | C13B—H13B | 0.9300 |
C2B—N1B | 1.352 (3) | C14A—O4A | 1.187 (4) |
C3A—N3A | 1.275 (3) | C14A—O3A | 1.350 (4) |
C3A—N2A | 1.379 (3) | C14A—C15A | 1.451 (4) |
C3A—S1A | 1.742 (3) | C14B—O4B | 1.202 (4) |
C3B—N3B | 1.271 (3) | C14B—O3B | 1.353 (4) |
C3B—N2B | 1.379 (3) | C14B—C15B | 1.455 (4) |
C3B—S1B | 1.741 (3) | C15A—C16A | 1.325 (4) |
C4A—O2A | 1.209 (3) | C15A—H15A | 0.9300 |
C4A—N2A | 1.370 (3) | C15B—C16B | 1.310 (4) |
C4A—C5A | 1.486 (4) | C15B—H15B | 0.9300 |
C4B—O2B | 1.206 (4) | C16A—C17A | 1.457 (4) |
C4B—N2B | 1.362 (4) | C16A—H16A | 0.9300 |
C4B—C5B | 1.495 (4) | C16B—C17B | 1.457 (4) |
C5A—H5A1 | 0.9600 | C16B—H16B | 0.9300 |
C5A—H5A2 | 0.9600 | C17A—C18A | 1.379 (5) |
C5A—H5A3 | 0.9600 | C17A—C22A | 1.388 (4) |
C5B—H5B1 | 0.9600 | C17B—C22B | 1.378 (4) |
C5B—H5B2 | 0.9600 | C17B—C18B | 1.379 (4) |
C5B—H5B3 | 0.9600 | C18A—C19A | 1.378 (5) |
C6A—N1A | 1.484 (3) | C18A—H18A | 0.9300 |
C6A—C8A | 1.508 (4) | C18B—C19B | 1.373 (5) |
C6A—C7A | 1.533 (4) | C18B—H18B | 0.9300 |
C6A—S1A | 1.863 (3) | C19A—C20A | 1.372 (6) |
C6B—N1B | 1.499 (3) | C19A—H19A | 0.9300 |
C6B—C8B | 1.523 (3) | C19B—C20B | 1.348 (7) |
C6B—C7B | 1.531 (4) | C19B—H19B | 0.9300 |
C6B—S1B | 1.845 (3) | C20A—C21A | 1.358 (6) |
C7A—H7A1 | 0.9600 | C20A—H20A | 0.9300 |
C7A—H7A2 | 0.9600 | C20B—C21B | 1.355 (6) |
C7A—H7A3 | 0.9600 | C20B—H20B | 0.9300 |
C7B—H7B1 | 0.9600 | C21A—C22A | 1.378 (5) |
C7B—H7B2 | 0.9600 | C21A—H21A | 0.9300 |
C7B—H7B3 | 0.9600 | C21B—C22B | 1.364 (5) |
C8A—C9A | 1.386 (4) | C21B—H21B | 0.9300 |
C8A—C13A | 1.388 (4) | C22A—H22A | 0.9300 |
C8B—C13B | 1.371 (4) | C22B—H22B | 0.9300 |
C8B—C9B | 1.373 (4) | C24—Cl2 | 1.669 (6) |
C9A—C10A | 1.375 (4) | C24—Cl3 | 1.718 (6) |
C9A—H9A | 0.9300 | C24—Cl1 | 1.761 (7) |
C9B—C10B | 1.363 (4) | C24—H24 | 0.9800 |
C9B—H9B | 0.9300 | N1A—N3A | 1.396 (3) |
C10A—C11A | 1.370 (4) | N1B—N3B | 1.395 (3) |
C10A—H10A | 0.9300 | N2A—H2A | 0.8600 |
C10B—C11B | 1.362 (4) | N2B—H2B | 0.8600 |
C2A—C1A—H1A1 | 109.5 | C13A—C12A—C11A | 119.2 (3) |
C2A—C1A—H1A2 | 109.5 | C13A—C12A—H12A | 120.4 |
H1A1—C1A—H1A2 | 109.5 | C11A—C12A—H12A | 120.4 |
C2A—C1A—H1A3 | 109.5 | C11B—C12B—C13B | 119.7 (3) |
H1A1—C1A—H1A3 | 109.5 | C11B—C12B—H12B | 120.1 |
H1A2—C1A—H1A3 | 109.5 | C13B—C12B—H12B | 120.1 |
C2B—C1B—H1B1 | 109.5 | C12A—C13A—C8A | 121.8 (3) |
C2B—C1B—H1B2 | 109.5 | C12A—C13A—H13A | 119.1 |
H1B1—C1B—H1B2 | 109.5 | C8A—C13A—H13A | 119.1 |
C2B—C1B—H1B3 | 109.5 | C8B—C13B—C12B | 121.4 (3) |
H1B1—C1B—H1B3 | 109.5 | C8B—C13B—H13B | 119.3 |
H1B2—C1B—H1B3 | 109.5 | C12B—C13B—H13B | 119.3 |
O1A—C2A—N1A | 120.1 (3) | O4A—C14A—O3A | 122.9 (3) |
O1A—C2A—C1A | 122.7 (2) | O4A—C14A—C15A | 126.1 (3) |
N1A—C2A—C1A | 117.2 (3) | O3A—C14A—C15A | 111.0 (3) |
O1B—C2B—N1B | 119.5 (2) | O4B—C14B—O3B | 122.5 (3) |
O1B—C2B—C1B | 122.4 (2) | O4B—C14B—C15B | 126.1 (3) |
N1B—C2B—C1B | 118.1 (2) | O3B—C14B—C15B | 111.4 (3) |
N3A—C3A—N2A | 119.8 (2) | C16A—C15A—C14A | 121.0 (3) |
N3A—C3A—S1A | 118.7 (2) | C16A—C15A—H15A | 119.5 |
N2A—C3A—S1A | 121.56 (18) | C14A—C15A—H15A | 119.5 |
N3B—C3B—N2B | 119.9 (2) | C16B—C15B—C14B | 121.8 (3) |
N3B—C3B—S1B | 118.86 (19) | C16B—C15B—H15B | 119.1 |
N2B—C3B—S1B | 121.26 (19) | C14B—C15B—H15B | 119.1 |
O2A—C4A—N2A | 121.2 (3) | C15A—C16A—C17A | 128.1 (3) |
O2A—C4A—C5A | 122.9 (3) | C15A—C16A—H16A | 115.9 |
N2A—C4A—C5A | 115.9 (2) | C17A—C16A—H16A | 115.9 |
O2B—C4B—N2B | 121.5 (3) | C15B—C16B—C17B | 127.8 (3) |
O2B—C4B—C5B | 123.0 (3) | C15B—C16B—H16B | 116.1 |
N2B—C4B—C5B | 115.5 (3) | C17B—C16B—H16B | 116.1 |
C4A—C5A—H5A1 | 109.5 | C18A—C17A—C22A | 118.0 (3) |
C4A—C5A—H5A2 | 109.5 | C18A—C17A—C16A | 123.0 (3) |
H5A1—C5A—H5A2 | 109.5 | C22A—C17A—C16A | 119.0 (3) |
C4A—C5A—H5A3 | 109.5 | C22B—C17B—C18B | 117.7 (3) |
H5A1—C5A—H5A3 | 109.5 | C22B—C17B—C16B | 123.5 (3) |
H5A2—C5A—H5A3 | 109.5 | C18B—C17B—C16B | 118.9 (3) |
C4B—C5B—H5B1 | 109.5 | C19A—C18A—C17A | 120.6 (4) |
C4B—C5B—H5B2 | 109.5 | C19A—C18A—H18A | 119.7 |
H5B1—C5B—H5B2 | 109.5 | C17A—C18A—H18A | 119.7 |
C4B—C5B—H5B3 | 109.5 | C19B—C18B—C17B | 120.3 (4) |
H5B1—C5B—H5B3 | 109.5 | C19B—C18B—H18B | 119.8 |
H5B2—C5B—H5B3 | 109.5 | C17B—C18B—H18B | 119.8 |
N1A—C6A—C8A | 111.2 (2) | C20A—C19A—C18A | 120.5 (4) |
N1A—C6A—C7A | 112.5 (2) | C20A—C19A—H19A | 119.7 |
C8A—C6A—C7A | 114.9 (2) | C18A—C19A—H19A | 119.7 |
N1A—C6A—S1A | 101.33 (16) | C20B—C19B—C18B | 120.7 (4) |
C8A—C6A—S1A | 108.81 (17) | C20B—C19B—H19B | 119.6 |
C7A—C6A—S1A | 107.09 (18) | C18B—C19B—H19B | 119.6 |
N1B—C6B—C8B | 110.5 (2) | C21A—C20A—C19A | 119.6 (4) |
N1B—C6B—C7B | 111.1 (2) | C21A—C20A—H20A | 120.2 |
C8B—C6B—C7B | 115.2 (2) | C19A—C20A—H20A | 120.2 |
N1B—C6B—S1B | 102.28 (15) | C19B—C20B—C21B | 119.9 (4) |
C8B—C6B—S1B | 109.63 (16) | C19B—C20B—H20B | 120.1 |
C7B—C6B—S1B | 107.21 (19) | C21B—C20B—H20B | 120.1 |
C6A—C7A—H7A1 | 109.5 | C20A—C21A—C22A | 120.4 (3) |
C6A—C7A—H7A2 | 109.5 | C20A—C21A—H21A | 119.8 |
H7A1—C7A—H7A2 | 109.5 | C22A—C21A—H21A | 119.8 |
C6A—C7A—H7A3 | 109.5 | C20B—C21B—C22B | 120.1 (4) |
H7A1—C7A—H7A3 | 109.5 | C20B—C21B—H21B | 119.9 |
H7A2—C7A—H7A3 | 109.5 | C22B—C21B—H21B | 119.9 |
C6B—C7B—H7B1 | 109.5 | C21A—C22A—C17A | 120.9 (3) |
C6B—C7B—H7B2 | 109.5 | C21A—C22A—H22A | 119.6 |
H7B1—C7B—H7B2 | 109.5 | C17A—C22A—H22A | 119.6 |
C6B—C7B—H7B3 | 109.5 | C21B—C22B—C17B | 121.2 (3) |
H7B1—C7B—H7B3 | 109.5 | C21B—C22B—H22B | 119.4 |
H7B2—C7B—H7B3 | 109.5 | C17B—C22B—H22B | 119.4 |
C9A—C8A—C13A | 117.6 (3) | Cl2—C24—Cl3 | 112.3 (4) |
C9A—C8A—C6A | 121.6 (2) | Cl2—C24—Cl1 | 111.7 (3) |
C13A—C8A—C6A | 120.7 (2) | Cl3—C24—Cl1 | 108.8 (4) |
C13B—C8B—C9B | 117.3 (2) | Cl2—C24—H24 | 107.9 |
C13B—C8B—C6B | 119.6 (2) | Cl3—C24—H24 | 107.9 |
C9B—C8B—C6B | 123.0 (2) | Cl1—C24—H24 | 107.9 |
C10A—C9A—C8A | 121.1 (3) | C2A—N1A—N3A | 118.9 (2) |
C10A—C9A—H9A | 119.4 | C2A—N1A—C6A | 123.1 (2) |
C8A—C9A—H9A | 119.4 | N3A—N1A—C6A | 117.22 (19) |
C10B—C9B—C8B | 121.3 (3) | C2B—N1B—N3B | 119.7 (2) |
C10B—C9B—H9B | 119.4 | C2B—N1B—C6B | 122.5 (2) |
C8B—C9B—H9B | 119.4 | N3B—N1B—C6B | 117.59 (19) |
C11A—C10A—C9A | 119.7 (3) | C4A—N2A—C3A | 124.2 (2) |
C11A—C10A—H10A | 120.1 | C4A—N2A—H2A | 117.9 |
C9A—C10A—H10A | 120.1 | C3A—N2A—H2A | 117.9 |
C11B—C10B—C9B | 119.9 (3) | C4B—N2B—C3B | 124.3 (2) |
C11B—C10B—H10B | 120.0 | C4B—N2B—H2B | 117.8 |
C9B—C10B—H10B | 120.0 | C3B—N2B—H2B | 117.8 |
C10A—C11A—C12A | 120.6 (3) | C3A—N3A—N1A | 110.1 (2) |
C10A—C11A—O3A | 116.6 (3) | C3B—N3B—N1B | 110.6 (2) |
C12A—C11A—O3A | 122.7 (3) | C14A—O3A—C11A | 119.8 (2) |
C12B—C11B—C10B | 120.3 (3) | C14B—O3B—C11B | 117.8 (2) |
C12B—C11B—O3B | 120.9 (3) | C3A—S1A—C6A | 89.27 (11) |
C10B—C11B—O3B | 118.6 (3) | C3B—S1B—C6B | 90.27 (11) |
N1A—C6A—C8A—C9A | 18.9 (3) | C18B—C17B—C22B—C21B | −1.6 (5) |
C7A—C6A—C8A—C9A | 148.1 (3) | C16B—C17B—C22B—C21B | 179.2 (3) |
S1A—C6A—C8A—C9A | −91.9 (3) | O1A—C2A—N1A—N3A | 174.7 (2) |
N1A—C6A—C8A—C13A | −164.1 (2) | C1A—C2A—N1A—N3A | −4.5 (4) |
C7A—C6A—C8A—C13A | −34.9 (3) | O1A—C2A—N1A—C6A | 5.1 (4) |
S1A—C6A—C8A—C13A | 85.1 (3) | C1A—C2A—N1A—C6A | −174.1 (3) |
N1B—C6B—C8B—C13B | 63.4 (3) | C8A—C6A—N1A—C2A | 73.6 (3) |
C7B—C6B—C8B—C13B | −169.6 (3) | C7A—C6A—N1A—C2A | −56.8 (3) |
S1B—C6B—C8B—C13B | −48.6 (3) | S1A—C6A—N1A—C2A | −170.9 (2) |
N1B—C6B—C8B—C9B | −115.5 (3) | C8A—C6A—N1A—N3A | −96.1 (2) |
C7B—C6B—C8B—C9B | 11.5 (4) | C7A—C6A—N1A—N3A | 133.4 (2) |
S1B—C6B—C8B—C9B | 132.5 (3) | S1A—C6A—N1A—N3A | 19.4 (2) |
C13A—C8A—C9A—C10A | −0.4 (4) | O1B—C2B—N1B—N3B | 178.5 (2) |
C6A—C8A—C9A—C10A | 176.7 (3) | C1B—C2B—N1B—N3B | −2.1 (4) |
C13B—C8B—C9B—C10B | 0.6 (5) | O1B—C2B—N1B—C6B | 3.1 (4) |
C6B—C8B—C9B—C10B | 179.5 (3) | C1B—C2B—N1B—C6B | −177.6 (2) |
C8A—C9A—C10A—C11A | −0.1 (5) | C8B—C6B—N1B—C2B | 65.2 (3) |
C8B—C9B—C10B—C11B | −1.2 (5) | C7B—C6B—N1B—C2B | −64.0 (3) |
C9A—C10A—C11A—C12A | 0.4 (5) | S1B—C6B—N1B—C2B | −178.2 (2) |
C9A—C10A—C11A—O3A | −175.4 (3) | C8B—C6B—N1B—N3B | −110.4 (2) |
C9B—C10B—C11B—C12B | 0.9 (5) | C7B—C6B—N1B—N3B | 120.4 (2) |
C9B—C10B—C11B—O3B | −174.3 (3) | S1B—C6B—N1B—N3B | 6.3 (2) |
C10A—C11A—C12A—C13A | −0.1 (5) | O2A—C4A—N2A—C3A | −5.8 (4) |
O3A—C11A—C12A—C13A | 175.4 (3) | C5A—C4A—N2A—C3A | 172.6 (3) |
C10B—C11B—C12B—C13B | 0.1 (6) | N3A—C3A—N2A—C4A | 174.3 (2) |
O3B—C11B—C12B—C13B | 175.2 (3) | S1A—C3A—N2A—C4A | −7.2 (4) |
C11A—C12A—C13A—C8A | −0.4 (4) | O2B—C4B—N2B—C3B | −0.7 (5) |
C9A—C8A—C13A—C12A | 0.7 (4) | C5B—C4B—N2B—C3B | 178.8 (3) |
C6A—C8A—C13A—C12A | −176.5 (3) | N3B—C3B—N2B—C4B | 176.4 (3) |
C9B—C8B—C13B—C12B | 0.4 (5) | S1B—C3B—N2B—C4B | −4.9 (4) |
C6B—C8B—C13B—C12B | −178.5 (3) | N2A—C3A—N3A—N1A | 178.5 (2) |
C11B—C12B—C13B—C8B | −0.7 (6) | S1A—C3A—N3A—N1A | 0.0 (3) |
O4A—C14A—C15A—C16A | 2.2 (5) | C2A—N1A—N3A—C3A | 175.8 (2) |
O3A—C14A—C15A—C16A | −176.0 (3) | C6A—N1A—N3A—C3A | −14.0 (3) |
O4B—C14B—C15B—C16B | −14.4 (5) | N2B—C3B—N3B—N1B | 178.6 (2) |
O3B—C14B—C15B—C16B | 165.3 (3) | S1B—C3B—N3B—N1B | −0.2 (3) |
C14A—C15A—C16A—C17A | −180.0 (3) | C2B—N1B—N3B—C3B | 179.9 (2) |
C14B—C15B—C16B—C17B | −177.9 (3) | C6B—N1B—N3B—C3B | −4.4 (3) |
C15A—C16A—C17A—C18A | −5.9 (5) | O4A—C14A—O3A—C11A | −2.0 (5) |
C15A—C16A—C17A—C22A | 171.7 (3) | C15A—C14A—O3A—C11A | 176.3 (2) |
C15B—C16B—C17B—C22B | −9.2 (5) | C10A—C11A—O3A—C14A | −125.4 (3) |
C15B—C16B—C17B—C18B | 171.7 (3) | C12A—C11A—O3A—C14A | 58.9 (4) |
C22A—C17A—C18A—C19A | 1.0 (6) | O4B—C14B—O3B—C11B | 5.0 (5) |
C16A—C17A—C18A—C19A | 178.6 (4) | C15B—C14B—O3B—C11B | −174.7 (3) |
C22B—C17B—C18B—C19B | 0.9 (6) | C12B—C11B—O3B—C14B | 68.0 (4) |
C16B—C17B—C18B—C19B | −179.8 (4) | C10B—C11B—O3B—C14B | −116.7 (3) |
C17A—C18A—C19A—C20A | −0.9 (7) | N3A—C3A—S1A—C6A | 9.8 (2) |
C17B—C18B—C19B—C20B | 0.6 (7) | N2A—C3A—S1A—C6A | −168.6 (2) |
C18A—C19A—C20A—C21A | 0.0 (7) | N1A—C6A—S1A—C3A | −14.77 (17) |
C18B—C19B—C20B—C21B | −1.5 (8) | C8A—C6A—S1A—C3A | 102.52 (18) |
C19A—C20A—C21A—C22A | 0.7 (6) | C7A—C6A—S1A—C3A | −132.8 (2) |
C19B—C20B—C21B—C22B | 0.9 (7) | N3B—C3B—S1B—C6B | 3.4 (2) |
C20A—C21A—C22A—C17A | −0.5 (5) | N2B—C3B—S1B—C6B | −175.3 (2) |
C18A—C17A—C22A—C21A | −0.4 (5) | N1B—C6B—S1B—C3B | −4.89 (16) |
C16A—C17A—C22A—C21A | −178.1 (3) | C8B—C6B—S1B—C3B | 112.41 (18) |
C20B—C21B—C22B—C17B | 0.7 (7) | C7B—C6B—S1B—C3B | −121.86 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2A—H2A···O1Bi | 0.86 | 1.96 | 2.815 (3) | 172 |
N2B—H2B···O1Aii | 0.86 | 1.96 | 2.810 (3) | 169 |
C5A—H5A2···O1Bi | 0.96 | 2.56 | 3.344 (4) | 139 |
C5A—H5A3···O4Ai | 0.96 | 2.54 | 3.477 (4) | 164 |
C12B—H12B···O2Aiii | 0.93 | 2.56 | 3.459 (4) | 161 |
Symmetry codes: (i) x, y−1, z; (ii) −x+1, −y+1, −z; (iii) x−1, y+1, z. |
Acknowledgements
The authors are grateful to the SAIF, IIT, Madras, India, for the data collection.
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