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ISSN: 2056-9890

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

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 6 August 2019; accepted 28 August 2019; online 10 September 2019)

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 asymmetric unit in the triclinic P[\overline{1}] space group. 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 envelope conformation, 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 heterocyclic compounds are one of the most important classes of biologically active compounds, exhibiting anti­microbial, anti­tumour and anti–inflammatory (Sethuram et al., 2013[Sethuram, M., Rajasekharan, M. V., Dhandapani, M., Amirthaganesan, G. & NizamMohideen, M. (2013). Acta Cryst. E69, o957-o958.]; Huq et al., 2010[Huq, C. A. M. A., Sivakumar, S. & NizamMohideen, M. (2010). Acta Cryst. E66, o2462.], Rajkumar et al., 2014[Rajkumar, M. A., Xavier, S. S. J., Anbarasu, S., Devarajan, P. A. & NizamMohideen, M. (2014). Acta Cryst. E70, o473-o474.], 2015[Rajkumar, M. A., NizamMohideen, M., Xavier, S. S. J., Anbarasu, S. & Devarajan, D. P. A. (2015). Acta Cryst. E71, 231-233.]; Thirunavukkarsu et al., 2017[Thirunavukkarsu, A., Sujatha, T., Umarani, P. R., Nizam Mohideen, M., Silambarasan, A. & Mohan Kumar, R. (2017). J. Cryst. Growth, 460, 42-47.]; Babu et al., 2014a[Babu, K. S. S., Peramaiyan, G., NizamMohideen, M. & Mohan, R. (2014a). Acta Cryst. E70, o391-o392.],b[Babu, K. S. S., Dhavamurthy, M., NizamMohideen, M., Peramaiyan, G. & Mohan, R. (2014b). Acta Cryst. E70, o600-o601.]) 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[Udupi, R. H., Suresh, G. V., Sety, S. R. & Bhat, A. R. (2000). J. Indian Chem. Soc. 77, 302-304.]), herbicidal anti­microbial, bactericidal (Tehranchian et al., 2005[Tehranchian, S., Akbarzadeh, T., Fazeli, R. M., Jamalifar, H. & Shafiee, A. (2005). Bioorg. Med. Chem. Lett. 15, 1023-1025.]), anti­viral and anti-HIV-1 (Invidiata et al., 1996[Invidiata, F. P., Simoni, D., Scintu, F. & Pinna, N. (1996). Farmaco, 51, 659-664.]) 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 ketones 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.

[Scheme 1]

2. 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[link], 2[link], 3[link] and 4[link], 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[Aridoss, G., Amirthaganesan, S., Velmurugan, D., Kim, S. H. & Jeong, Y. T. (2008). Acta Cryst. E64, o2096.]).

[Figure 1]
Figure 1
View of the mol­ecular structure of compound I, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level. The minor disordered components have been omitted.
[Figure 2]
Figure 2
View of the mol­ecular structure of compound II, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level. The solvent water mol­ecule and the minor disordered component have been omitted.
[Figure 3]
Figure 3
View of the mol­ecular structure of compound III, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level. The minor disordered component has been omitted.
[Figure 4]
Figure 4
View of the mol­ecular structure of compound IV, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level. The solvent CHCl3 mol­ecule has been omitted.

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[link], 2[link], 3[link] and 4[link], and Figs. 5[link], 6[link], 7[link] and 8[link]).

Table 1
Hydrogen-bond geometry (Å, °) for I[link]

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 DA 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—H17BCg2v 0.93 2.91 3.664 (8) 139
C17C—H17CCg6v 0.93 2.98 3.776 (10) 145
C20C—H20CCg3vi 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.

Table 2
Hydrogen-bond geometry (Å, °) for II[link]

Cg2 and Cg4 are the centroids of the C8B–C13B and C8A–C13A rings, respectively.

D—H⋯A D—H H⋯A DA 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—H15ACg2iv 0.98 2.99 3.959 (4) 168
C17B—H17BCg4iv 0.96 2.98 3.864 (9) 153
C17′—H17HCg4iv 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.

Table 3
Hydrogen-bond geometry (Å, °) for III[link]

D—H⋯A D—H H⋯A DA 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.

Table 4
Hydrogen-bond geometry (Å, °) for IV[link]

D—H⋯A D—H H⋯A DA 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.
[Figure 5]
Figure 5
The crystal packing of compound I, viewed along the a axis. The hydrogen bonds (see Table 1[link]) are shown as dashed lines. For clarity, the H atoms not involved in the hydrogen bonding have been omitted.
[Figure 6]
Figure 6
Part of the crystal structure of II, viewed along the a axis. The hydrogen bonds (see Table 2[link]) are shown as dashed lines. For clarity, the H atoms not involved in the hydrogen bonding have been omitted.
[Figure 7]
Figure 7
The crystal packing of compound III, viewed along the b axis. The hydrogen bonds (see Table 3[link]) are shown as dashed lines. For clarity, the H atoms not involved in the hydrogen bonding have been omitted.
[Figure 8]
Figure 8
The crystal packing of compound IV, viewed along the b axis. The hydrogen bonds (see Table 4[link]) are shown as dashed lines. For clarity, the H atoms not involved in the hydrogen bonding have been omitted.

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[Tan, S. L., Jotani, M. M. & Tiekink, E. R. T. (2019). Acta Cryst. E75, 308-318.]) reviews and describes the uses and utility of Hirshfeld surface analysis (Spackman & Jayatilaka, 2009[Spackman, M. A. & Jayatilaka, D. (2009). CrystEngComm, 11, 19-32.]), and the associated two-dimensional fingerprint plots (McKinnon et al., 2007[McKinnon, J. J., Jayatilaka, D. & Spackman, M. A. (2007). Chem. Commun. pp. 3814-3816.]), to analyse inter­molecular contacts in crystals. The various calculations were performed with CrystalExplorer17 (Turner et al., 2017[Turner, M. J., McKinnon, J. J., Wolff, S. K., Grimwood, D. J., Spackman, P. R., Jayatilaka, D. & Spackman, M. A. (2017). CrystalExplorer17. University of Western Australia. http://hirshfeldsurface.net]).

The Hirshfeld surfaces of compounds IIV mapped over dnorm are given in Fig. 9[link], and the inter­molecular contacts are illustrated in Fig. 10[link] for I, Fig. 11[link] for II, Fig. 12[link] for III and Fig. 13[link] 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.

[Figure 9]
Figure 9
The Hirshfeld surfaces of compounds (a) I, (b) II, (c) III and (d) IV mapped over dnorm
[Figure 10]
Figure 10
A view of the Hirshfeld surface mapped over dnorm of compound I, showing the various inter­molecular contacts in the crystal.
[Figure 11]
Figure 11
A view of the Hirshfeld surface mapped over dnorm of compound II, showing the various inter­molecular contacts in the crystal.
[Figure 12]
Figure 12
A view of the Hirshfeld surface mapped over dnorm of compound III, showing the various inter­molecular contacts in the crystal.
[Figure 13]
Figure 13
A view of the Hirshfeld surface mapped over dnorm of compound IV, showing the various inter­molecular contacts in the crystal.

The fingerprint plots are given in Figs. 14[link], 15[link], 16[link] and 17[link], 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. 14[link]b), O⋯H/H⋯O at 24.2% (Fig. 14[link]c), C⋯H/H⋯C contacts at 21.3% (Fig. 14[link]d) and N⋯H/H⋯N at 5.2% (Fig. 14[link]e), followed by the S⋯H/H⋯S at 4.1% (Fig. 14[link]f). For compound II, the principal inter­molecular contacts are H⋯H at 50.0% (Fig. 15[link]b), O⋯H/H⋯O at 23.3% (Fig. 15[link]c), C⋯H/H⋯C contacts at 14.2% (Fig. 15[link]d) and N⋯H/H⋯N at 5.3% (Fig. 15[link]e) followed by the S⋯H/H⋯S at 4.4% (Fig. 15[link]f). For compound III, the principal inter­molecular contacts are H⋯H at 51.0% (Fig. 16[link]b), O⋯H/H⋯O at 26.4% (Fig. 16[link]c), C⋯H/H⋯C contacts at 8.3% (Fig. 16[link]d) and S⋯H/H⋯S at 4.4% (Fig. 15[link]e) followed by the N⋯H/H⋯N at 4.1% (Fig. 15[link]f) and C⋯ C contacts at 1.5%. For compound IV, the principal inter­molecular contacts are H⋯H at 35.3% (Fig. 17[link]b), O⋯H/H⋯O at 20.0% (Fig. 17[link]c), Cl⋯H/H⋯Cl at 15.7% (Fig. 17[link]d), C⋯H/H⋯C at 13.7% (Fig. 17[link]e), S⋯H/H⋯S at 3.3% (Fig. 17[link]f), N⋯H/H⋯N at 3.3% (Fig. 17[link]c) followed by the C⋯C contacts at 1.6% (Fig. 17[link]h). In all compounds, the H⋯H inter­molecular contacts predominate, followed by the O⋯H/H⋯O contacts.

[Figure 14]
Figure 14
The full two-dimensional fingerprint plot for compound I, and fingerprint plots delineated into (b) H⋯H, (c) O⋯H/H⋯O, (d) C⋯H/H⋯C (e) N⋯H/H⋯N and (f) S⋯H/H⋯S contacts.
[Figure 15]
Figure 15
The full two-dimensional fingerprint plot for compound II, and fingerprint plots delineated into (b) H⋯H, (c) O⋯H/H⋯O, (d) C⋯H/H⋯C (e) N⋯H/H⋯N and (f) S⋯H/H⋯S contacts.
[Figure 16]
Figure 16
The full two-dimensional fingerprint plot for compound III, and fingerprint plots delineated into (b) H⋯H, (c) O⋯H/H⋯O, (d) C⋯H/H⋯C (e) S⋯H/H⋯S, (f) N⋯H/H⋯N and (g) C⋯C contacts.
[Figure 17]
Figure 17
The full two-dimensional fingerprint plot for compound IV, and fingerprint plots delineated into (b) H⋯H, (c) O⋯H/H⋯O, (d) Cl⋯H/H⋯Cl, (e) C⋯H/H⋯C, (f) S⋯H/H⋯S, (g) N⋯·H/H⋯N and (h) C⋯C contacts.

5. Database survey

A search of the Cambridge Structural Database (Version 5.40, last update May 2019; Groom et al., 2016[Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171-179.]) 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[Kavitha, H. D., Marganakop, S. B., Kamble, R. R., Roopashree, K. R. & Devarajegowda, H. C. (2013). Acta Cryst. E69, o701-o702.]), N-(4-acetyl-5-(3-meth­oxy­phen­yl)-4,5-di­hydro-1,3,4-thia­diazol-2-yl) acetamide (IGAREO; Aridoss et al., 2008[Aridoss, G., Amirthaganesan, S., Velmurugan, D., Kim, S. H. & Jeong, Y. T. (2008). Acta Cryst. E64, o2096.]), that crystallized in space group P21 with two independent mol­ecules in the asymmetric unit, and 2-acetyl­amino-4-acetyl-5-phenyl-Δ2-1,3,4-thia­diazo­line (YOLKAL; Usova et al., 1994[Usova, E. B., Krapivin, G. D., Zavodnik, V. E. & Kul'nevich, V. G. (1994). Chem. Heterocycl. Compd, 30, 1337-1344.]). 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 refinement details are summarized in Table 5[link]. 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.

Table 5
Experimental details

  I II III IV
Crystal data
Chemical formula C20H19N3O4S C17H21N3O4S·0.25H2O C16H19N3O4S C22H21N3O4S·0.5CHCl3
Mr 397.44 367.93 349.40 483.16
Crystal system, space group Triclinic, P[\overline{1}] Triclinic, P[\overline{1}] Triclinic, P[\overline{1}] Triclinic, P[\overline{1}]
Temperature (K) 293 293 293 293
a, b, c (Å) 6.7559 (1), 16.9258 (2), 19.0611 (3) 6.7802 (1), 17.2671 (4), 17.3089 (4) 11.4150 (3), 12.4021 (3), 13.2305 (3) 10.7427 (1), 11.0828 (2), 20.8969 (3)
α, β, γ (°) 110.447 (1), 96.854 (2), 93.370 (1) 108.224 (1), 99.084 (1), 96.720 (1) 71.982 (1), 89.829 (1), 83.114 (1) 93.186 (1), 103.945 (4), 98.489 (2)
V3) 2015.84 (5) 1870.50 (7) 1767.18 (8) 2377.39 (7)
Z 4 4 4 4
Radiation type Mo Kα Mo Kα Mo Kα Mo Kα
μ (mm−1) 0.19 0.20 0.21 0.34
Crystal size (mm) 0.30 × 0.25 × 0.20 0.30 × 0.25 × 0.20 0.25 × 0.24 × 0.20 0.30 × 0.25 × 0.20
 
Data collection
Diffractometer Bruker Kappa APEXII CCD Bruker Kappa APEXII CCD Bruker Kappa APEXII CCD Bruker Kappa APEXII CCD
Absorption correction Multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.648, 0.763 0.660, 0.746 0.756, 0.824 0.741, 0.856
No. of measured, independent and observed [I > 2σ(I)] reflections 27547, 7061, 4821 27060, 7680, 5737 26933, 7257, 5869 31719, 8335, 6495
Rint 0.029 0.030 0.022 0.027
(sin θ/λ)max−1) 0.595 0.627 0.627 0.595
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.060, 0.226, 0.83 0.053, 0.169, 1.04 0.037, 0.106, 1.03 0.058, 0.195, 1.09
No. of reflections 7061 7680 7257 8335
No. of parameters 635 525 451 583
No. of restraints 523 242 0 0
H-atom treatment H atoms treated by a mixture of independent and constrained refinement H atoms treated by a mixture of independent and constrained refinement H-atom parameters constrained H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.38, −0.56 0.48, −0.38 0.24, −0.33 0.54, −0.60
Computer programs: APEX2 and SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS2018/3 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2018/3 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), ORTEP-3 for Windows and WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]), Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]), PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925. ]).

Supporting information


Computing details top

For all structures, data collection: APEX2 (Bruker, 2008). Cell refinement: 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).

4-(5-Acetamido-3-acetyl-2-methyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)phenyl benzoate (I) top
Crystal data top
C20H19N3O4SZ = 4
Mr = 397.44F(000) = 832
Triclinic, P1Dx = 1.310 Mg m3
a = 6.7559 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 16.9258 (2) ÅCell parameters from 7061 reflections
c = 19.0611 (3) Åθ = 1.2–25.0°
α = 110.447 (1)°µ = 0.19 mm1
β = 96.854 (2)°T = 293 K
γ = 93.370 (1)°Block, colourless
V = 2015.84 (5) Å30.30 × 0.25 × 0.20 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer
4821 reflections with I > 2σ(I)
ω and φ scansRint = 0.029
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
θmax = 25.0°, θmin = 1.2°
Tmin = 0.648, Tmax = 0.763h = 88
27547 measured reflectionsk = 1720
7061 independent reflectionsl = 2222
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060Hydrogen site location: mixed
wR(F2) = 0.226H 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 parametersΔρmax = 0.38 e Å3
523 restraintsΔρmin = 0.56 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C1A0.2219 (6)0.4068 (2)0.0385 (2)0.0656 (9)
H1A10.1779580.4620860.0587770.098*
H1A20.1846050.3844590.0155650.098*
H1A30.3649710.4107300.0507860.098*
C2A0.1252 (5)0.34900 (19)0.07183 (18)0.0543 (8)
C6A0.0955 (5)0.20448 (19)0.08168 (18)0.0520 (7)
C3A0.3164 (4)0.16342 (18)0.02111 (17)0.0491 (7)
C4A0.4572 (5)0.0414 (2)0.10248 (19)0.0609 (9)
C5A0.6199 (7)0.0180 (2)0.1495 (2)0.0814 (11)
H5A10.7466040.0295170.1171870.122*
H5A20.6210920.0507330.1817430.122*
H5A30.5970160.0412450.1800530.122*
C7A0.1299 (5)0.1951 (2)0.0779 (2)0.0701 (10)
H7A10.1691660.2433200.1160420.105*
H7A20.1710800.1443980.0864860.105*
H7A30.1924340.1916640.0288490.105*
C8A0.2146 (5)0.22651 (19)0.16091 (18)0.0541 (8)
C9A0.4050 (5)0.2035 (2)0.1704 (2)0.0637 (9)
H9A0.4586780.1708270.1282590.076*
C10A0.5187 (7)0.2281 (3)0.2417 (3)0.0815 (12)
H10A0.6461250.2110830.2475110.098*
C11A0.4406 (9)0.2779 (3)0.3036 (2)0.0942 (15)
C12A0.2516 (9)0.3016 (3)0.2952 (3)0.1005 (15)
H12A0.1982920.3346620.3372390.121*
C13A0.1417 (7)0.2764 (3)0.2247 (2)0.0800 (11)
H13A0.0140740.2933920.2194690.096*
C5B0.3939 (6)0.4189 (2)0.1997 (3)0.0781 (11)
H5B10.3161320.4105870.2416350.117*
H5B20.3622020.3799590.1531060.117*
H5B30.5340220.4090080.2018440.117*
C4B0.3463 (5)0.5073 (2)0.2036 (2)0.0600 (8)
C3B0.1030 (5)0.60085 (19)0.17747 (17)0.0491 (7)
C6B0.0218 (5)0.75618 (19)0.21718 (18)0.0544 (8)
C7B0.0680 (6)0.8261 (2)0.1948 (2)0.0736 (10)
H7B10.0379460.8656640.1934450.110*
H7B20.1506340.8551540.2312920.110*
H7B30.1479480.8016360.1457280.110*
C8B0.1840 (5)0.78728 (19)0.28650 (17)0.0544 (8)
C13B0.2002 (7)0.8682 (3)0.3381 (2)0.0900 (14)
H13B0.1161980.9064770.3294690.108*
C12B0.3399 (9)0.8936 (3)0.4029 (3)0.119 (2)
H12B0.3474920.9483280.4383450.143*
C11B0.4662 (7)0.8387 (3)0.4147 (2)0.0940 (14)
C10B0.4553 (6)0.7583 (3)0.3638 (2)0.0811 (11)
H10B0.5418830.7206830.3722220.097*
C9B0.3147 (6)0.7332 (2)0.2996 (2)0.0699 (10)
H9B0.3080750.6784690.2643290.084*
C2B0.2436 (5)0.7107 (2)0.11765 (19)0.0609 (8)
C1B0.3273 (6)0.6394 (2)0.0626 (2)0.0734 (10)
H1B10.4155550.6614910.0362990.110*
H1B20.2197210.6019120.0267260.110*
H1B30.4004880.6088350.0890900.110*
N1A0.1674 (4)0.26824 (15)0.04924 (14)0.0506 (6)
N2A0.3109 (4)0.24387 (15)0.00068 (14)0.0499 (6)
N3A0.4450 (4)0.12653 (16)0.07072 (15)0.0528 (6)
H3A0.515 (5)0.152 (2)0.0914 (18)0.051 (9)*
N1B0.0966 (4)0.69192 (15)0.15279 (14)0.0532 (6)
N2B0.0369 (4)0.60619 (15)0.13948 (14)0.0529 (6)
N3B0.1812 (4)0.52161 (17)0.17374 (16)0.0549 (7)
H3B0.117 (6)0.482 (3)0.151 (2)0.080 (13)*
O1A0.0081 (4)0.37406 (15)0.11807 (15)0.0726 (7)
O2A0.3441 (5)0.00950 (15)0.09099 (17)0.0862 (8)
O1B0.3065 (4)0.78560 (15)0.13218 (16)0.0791 (8)
O2B0.4457 (4)0.56429 (18)0.23256 (19)0.0913 (9)
S1A0.15994 (13)0.10508 (5)0.01356 (5)0.0586 (3)
S1B0.18822 (13)0.69320 (5)0.23393 (6)0.0656 (3)
C14A0.697 (2)0.3397 (10)0.4045 (6)0.121 (3)0.553 (5)
C15A0.7452 (13)0.3657 (5)0.4903 (3)0.113 (3)0.553 (5)
C16A0.9402 (12)0.3664 (6)0.5236 (5)0.175 (4)0.553 (5)
H16A1.0329830.3385440.4941310.210*0.553 (5)
C17A0.9967 (13)0.4088 (7)0.6011 (5)0.181 (5)0.553 (5)
H17A1.1271420.4093080.6233660.217*0.553 (5)
C18A0.8581 (17)0.4505 (6)0.6452 (3)0.172 (5)0.553 (5)
H18A0.8958070.4788250.6969880.207*0.553 (5)
C19A0.6630 (15)0.4497 (6)0.6119 (4)0.155 (4)0.553 (5)
H19A0.5703110.4775790.6413750.185*0.553 (5)
C20A0.6066 (11)0.4073 (5)0.5344 (4)0.138 (4)0.553 (5)
H20A0.4761480.4068150.5121400.165*0.553 (5)
O3A0.5068 (13)0.3112 (7)0.3822 (5)0.102 (3)0.553 (5)
O4A0.754 (3)0.3795 (13)0.3656 (12)0.280 (10)0.553 (5)
C14C0.799 (2)0.3142 (11)0.3741 (8)0.121 (4)0.447 (5)
C15C0.8754 (14)0.3580 (5)0.4579 (4)0.120 (3)0.447 (5)
C16C0.8530 (11)0.3003 (5)0.4941 (4)0.091 (3)0.447 (5)
H16C0.7548030.2542220.4734760.110*0.447 (5)
C17C0.9775 (14)0.3113 (6)0.5611 (4)0.117 (4)0.447 (5)
H17C0.9624840.2727080.5853560.141*0.447 (5)
C18C1.1243 (15)0.3801 (7)0.5920 (4)0.157 (5)0.447 (5)
H18C1.2075160.3875400.6368200.189*0.447 (5)
C19C1.1466 (16)0.4379 (6)0.5558 (6)0.176 (5)0.447 (5)
H19C1.2448690.4838870.5764030.212*0.447 (5)
C20C1.0222 (17)0.4268 (6)0.4887 (5)0.162 (5)0.447 (5)
H20C1.0371900.4654030.4645220.194*0.447 (5)
O3C0.5988 (14)0.2887 (7)0.3676 (6)0.088 (3)0.447 (5)
O4C0.825 (2)0.3587 (10)0.3401 (9)0.173 (6)0.447 (5)
C14B0.7656 (13)0.8772 (6)0.4908 (5)0.083 (2)0.661 (6)
C15B0.8793 (11)0.8962 (5)0.5669 (3)0.073 (2)0.661 (6)
C16B0.7909 (7)0.8815 (4)0.6240 (5)0.085 (2)0.661 (6)
H16B0.6565880.8600850.6149830.103*0.661 (6)
C17B0.9034 (15)0.8987 (4)0.6947 (4)0.095 (2)0.661 (6)
H17B0.8442810.8888600.7329420.114*0.661 (6)
C18B1.1042 (14)0.9306 (5)0.7082 (3)0.092 (3)0.661 (6)
H18B1.1794350.9421750.7555130.110*0.661 (6)
C19B1.1925 (6)0.9453 (6)0.6511 (5)0.120 (3)0.661 (6)
H19B1.3269000.9667160.6601240.144*0.661 (6)
C20B1.0801 (13)0.9281 (6)0.5804 (4)0.110 (3)0.661 (6)
H20B1.1392110.9379420.5421640.132*0.661 (6)
O3B0.5721 (8)0.8573 (4)0.4871 (3)0.0906 (17)0.661 (6)
O4B0.8318 (9)0.8830 (5)0.4386 (3)0.149 (3)0.661 (6)
C14D0.6548 (19)0.8629 (9)0.5293 (7)0.083 (3)0.339 (6)
C15D0.8356 (19)0.8907 (10)0.5852 (9)0.072 (3)0.339 (6)
C16D0.8392 (18)0.8858 (10)0.6566 (11)0.093 (4)0.339 (6)
H16D0.7250400.8638450.6692720.112*0.339 (6)
C17D1.013 (3)0.9138 (10)0.7091 (6)0.093 (4)0.339 (6)
H17D1.0157120.9105450.7568820.112*0.339 (6)
C18D1.1839 (19)0.9466 (10)0.6901 (8)0.104 (5)0.339 (6)
H18D1.3004690.9653520.7252620.124*0.339 (6)
C19D1.1804 (18)0.9515 (11)0.6187 (11)0.113 (5)0.339 (6)
H19D1.2945560.9734600.6060310.136*0.339 (6)
C20D1.006 (3)0.9235 (12)0.5662 (6)0.096 (4)0.339 (6)
H20D1.0038850.9267620.5184200.115*0.339 (6)
O3D0.6689 (19)0.8790 (7)0.4661 (6)0.079 (3)0.339 (6)
O4D0.5080 (18)0.8298 (9)0.5407 (6)0.139 (5)0.339 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.082 (2)0.0410 (17)0.081 (2)0.0079 (16)0.0187 (19)0.0279 (16)
C2A0.0599 (19)0.0410 (17)0.0619 (19)0.0019 (14)0.0021 (16)0.0213 (14)
C6A0.0518 (17)0.0407 (16)0.0654 (19)0.0048 (13)0.0018 (14)0.0252 (14)
C3A0.0515 (17)0.0377 (15)0.0538 (17)0.0053 (13)0.0075 (13)0.0176 (13)
C4A0.075 (2)0.0353 (16)0.067 (2)0.0000 (15)0.0002 (17)0.0158 (14)
C5A0.098 (3)0.045 (2)0.099 (3)0.0096 (19)0.028 (2)0.0174 (19)
C7A0.0519 (19)0.062 (2)0.097 (3)0.0067 (16)0.0034 (18)0.034 (2)
C8A0.0619 (19)0.0423 (16)0.0616 (19)0.0037 (14)0.0047 (15)0.0261 (14)
C9A0.065 (2)0.057 (2)0.072 (2)0.0024 (16)0.0038 (17)0.0322 (17)
C10A0.080 (3)0.074 (3)0.092 (3)0.016 (2)0.024 (2)0.047 (2)
C11A0.125 (4)0.093 (3)0.062 (3)0.035 (3)0.020 (3)0.042 (2)
C12A0.134 (5)0.099 (4)0.061 (3)0.004 (3)0.009 (3)0.023 (2)
C13A0.084 (3)0.082 (3)0.073 (3)0.008 (2)0.013 (2)0.027 (2)
C5B0.073 (2)0.064 (2)0.107 (3)0.0018 (18)0.020 (2)0.043 (2)
C4B0.0521 (18)0.056 (2)0.073 (2)0.0013 (15)0.0055 (16)0.0262 (16)
C3B0.0529 (17)0.0436 (16)0.0526 (16)0.0054 (13)0.0018 (14)0.0212 (13)
C6B0.0614 (19)0.0404 (16)0.0644 (19)0.0082 (14)0.0101 (15)0.0217 (14)
C7B0.090 (3)0.052 (2)0.083 (2)0.0200 (18)0.004 (2)0.0297 (18)
C8B0.0645 (19)0.0435 (17)0.0562 (17)0.0099 (14)0.0134 (15)0.0171 (14)
C13B0.109 (3)0.061 (2)0.081 (3)0.032 (2)0.011 (2)0.006 (2)
C12B0.151 (5)0.076 (3)0.089 (3)0.040 (3)0.028 (3)0.010 (2)
C11B0.104 (3)0.091 (3)0.066 (2)0.024 (3)0.011 (2)0.007 (2)
C10B0.082 (3)0.079 (3)0.077 (2)0.027 (2)0.002 (2)0.024 (2)
C9B0.077 (2)0.050 (2)0.074 (2)0.0149 (17)0.0007 (18)0.0138 (17)
C2B0.077 (2)0.0447 (18)0.066 (2)0.0031 (16)0.0133 (17)0.0249 (15)
C1B0.085 (3)0.054 (2)0.084 (2)0.0020 (18)0.032 (2)0.0234 (18)
N1A0.0557 (15)0.0389 (13)0.0590 (15)0.0014 (11)0.0023 (12)0.0229 (11)
N2A0.0564 (15)0.0360 (13)0.0583 (14)0.0016 (11)0.0047 (12)0.0199 (11)
N3A0.0611 (16)0.0358 (13)0.0615 (16)0.0002 (12)0.0074 (13)0.0189 (12)
N1B0.0659 (16)0.0385 (13)0.0576 (15)0.0036 (11)0.0121 (12)0.0196 (11)
N2B0.0680 (17)0.0386 (13)0.0544 (14)0.0030 (12)0.0096 (13)0.0200 (11)
N3B0.0613 (17)0.0411 (14)0.0644 (16)0.0038 (12)0.0119 (13)0.0210 (12)
O1A0.0828 (17)0.0490 (13)0.0951 (18)0.0128 (12)0.0308 (15)0.0305 (12)
O2A0.106 (2)0.0383 (13)0.108 (2)0.0094 (13)0.0260 (17)0.0185 (13)
O1B0.1010 (19)0.0472 (14)0.0968 (19)0.0003 (13)0.0338 (15)0.0304 (13)
O2B0.0716 (17)0.0696 (18)0.141 (3)0.0123 (14)0.0387 (17)0.0395 (18)
S1A0.0671 (5)0.0373 (4)0.0682 (5)0.0104 (3)0.0025 (4)0.0201 (4)
S1B0.0620 (5)0.0485 (5)0.0884 (7)0.0101 (4)0.0214 (5)0.0231 (4)
C14A0.124 (7)0.141 (7)0.074 (6)0.007 (6)0.023 (5)0.021 (5)
C15A0.120 (7)0.113 (6)0.078 (5)0.017 (5)0.029 (5)0.020 (5)
C16A0.181 (7)0.174 (7)0.131 (6)0.015 (7)0.035 (6)0.029 (6)
C17A0.193 (10)0.194 (9)0.106 (7)0.027 (8)0.068 (7)0.029 (7)
C18A0.220 (12)0.186 (11)0.090 (7)0.049 (10)0.044 (8)0.058 (7)
C19A0.208 (11)0.159 (9)0.089 (6)0.044 (8)0.003 (7)0.053 (6)
C20A0.188 (10)0.130 (8)0.089 (6)0.027 (7)0.001 (6)0.046 (6)
O3A0.097 (6)0.141 (7)0.063 (4)0.025 (5)0.008 (4)0.041 (4)
O4A0.241 (16)0.301 (16)0.181 (14)0.081 (14)0.011 (12)0.026 (13)
C14C0.113 (8)0.165 (9)0.072 (7)0.030 (7)0.020 (6)0.043 (7)
C15C0.143 (8)0.130 (7)0.075 (6)0.036 (6)0.035 (5)0.046 (5)
C16C0.100 (6)0.097 (6)0.072 (5)0.004 (5)0.015 (5)0.033 (5)
C17C0.145 (8)0.136 (8)0.078 (6)0.008 (7)0.018 (6)0.059 (6)
C18C0.195 (11)0.151 (9)0.113 (7)0.007 (8)0.052 (8)0.059 (7)
C19C0.221 (10)0.163 (9)0.125 (8)0.058 (8)0.062 (8)0.067 (7)
C20C0.199 (10)0.142 (9)0.126 (8)0.065 (8)0.077 (8)0.071 (7)
O3C0.087 (6)0.116 (6)0.063 (5)0.021 (5)0.014 (4)0.047 (4)
O4C0.114 (8)0.234 (14)0.110 (9)0.007 (8)0.009 (7)0.001 (9)
C14B0.079 (5)0.095 (4)0.079 (5)0.005 (4)0.006 (4)0.038 (4)
C15B0.059 (4)0.073 (4)0.083 (4)0.001 (3)0.001 (3)0.027 (3)
C16B0.088 (4)0.085 (4)0.077 (5)0.000 (4)0.010 (4)0.029 (4)
C17B0.089 (6)0.099 (5)0.086 (5)0.009 (4)0.013 (4)0.030 (4)
C18B0.085 (6)0.105 (5)0.078 (4)0.004 (5)0.004 (4)0.031 (4)
C19B0.085 (5)0.163 (6)0.092 (7)0.002 (5)0.014 (5)0.033 (6)
C20B0.082 (6)0.150 (6)0.087 (5)0.008 (5)0.009 (4)0.039 (5)
O3B0.076 (3)0.119 (4)0.062 (3)0.006 (3)0.000 (3)0.018 (3)
O4B0.100 (4)0.248 (8)0.107 (4)0.043 (4)0.012 (3)0.092 (5)
C14D0.078 (6)0.089 (6)0.078 (6)0.006 (6)0.014 (6)0.027 (5)
C15D0.078 (6)0.074 (6)0.069 (6)0.007 (6)0.002 (6)0.034 (5)
C16D0.083 (7)0.100 (7)0.089 (8)0.006 (6)0.026 (7)0.039 (7)
C17D0.085 (9)0.103 (7)0.087 (6)0.009 (8)0.011 (7)0.041 (6)
C18D0.082 (8)0.134 (9)0.082 (9)0.008 (8)0.012 (8)0.031 (8)
C19D0.088 (8)0.151 (8)0.084 (9)0.002 (7)0.019 (7)0.034 (8)
C20D0.069 (8)0.123 (7)0.085 (6)0.007 (7)0.009 (6)0.030 (6)
O3D0.069 (7)0.095 (6)0.071 (6)0.004 (5)0.003 (5)0.033 (5)
O4D0.114 (8)0.198 (12)0.100 (8)0.038 (8)0.002 (6)0.062 (8)
Geometric parameters (Å, º) top
C1A—C2A1.499 (5)C2B—C1B1.488 (5)
C1A—H1A10.9600C1B—H1B10.9600
C1A—H1A20.9600C1B—H1B20.9600
C1A—H1A30.9600C1B—H1B30.9600
C2A—O1A1.236 (4)N1A—N2A1.400 (4)
C2A—N1A1.341 (4)N3A—H3A0.84 (3)
C6A—N1A1.503 (4)N1B—N2B1.408 (3)
C6A—C7A1.512 (5)N3B—H3B0.85 (4)
C6A—C8A1.533 (4)C14A—O4A1.239 (16)
C6A—S1A1.844 (3)C14A—O3A1.312 (13)
C3A—N2A1.282 (4)C14A—C15A1.526 (11)
C3A—N3A1.373 (4)C15A—C16A1.3900
C3A—S1A1.740 (3)C15A—C20A1.3900
C4A—O2A1.212 (4)C16A—C17A1.3900
C4A—N3A1.366 (4)C16A—H16A0.9300
C4A—C5A1.485 (5)C17A—C18A1.3900
C5A—H5A10.9600C17A—H17A0.9300
C5A—H5A20.9600C18A—C19A1.3900
C5A—H5A30.9600C18A—H18A0.9300
C7A—H7A10.9600C19A—C20A1.3900
C7A—H7A20.9600C19A—H19A0.9300
C7A—H7A30.9600C20A—H20A0.9300
C8A—C9A1.376 (5)C14C—O4C1.171 (15)
C8A—C13A1.382 (5)C14C—O3C1.370 (15)
C9A—C10A1.389 (5)C14C—C15C1.517 (13)
C9A—H9A0.9300C15C—C16C1.3900
C10A—C11A1.374 (7)C15C—C20C1.3900
C10A—H10A0.9300C16C—C17C1.3900
C11A—C12A1.369 (7)C16C—H16C0.9300
C11A—O3A1.407 (10)C17C—C18C1.3900
C11A—O3C1.473 (11)C17C—H17C0.9300
C12A—C13A1.364 (6)C18C—C19C1.3900
C12A—H12A0.9300C18C—H18C0.9300
C13A—H13A0.9300C19C—C20C1.3900
C5B—C4B1.487 (5)C19C—H19C0.9300
C5B—H5B10.9600C20C—H20C0.9300
C5B—H5B20.9600C14B—O4B1.170 (9)
C5B—H5B30.9600C14B—O3B1.318 (9)
C4B—O2B1.216 (4)C14B—C15B1.476 (9)
C4B—N3B1.357 (4)C15B—C16B1.3900
C3B—N2B1.275 (4)C15B—C20B1.3900
C3B—N3B1.387 (4)C16B—C17B1.3900
C3B—S1B1.735 (3)C16B—H16B0.9300
C6B—N1B1.492 (4)C17B—C18B1.3900
C6B—C8B1.525 (5)C17B—H17B0.9300
C6B—C7B1.525 (4)C18B—C19B1.3900
C6B—S1B1.849 (3)C18B—H18B0.9300
C7B—H7B10.9600C19B—C20B1.3900
C7B—H7B20.9600C19B—H19B0.9300
C7B—H7B30.9600C20B—H20B0.9300
C8B—C13B1.368 (5)C14D—O4D1.190 (13)
C8B—C9B1.372 (5)C14D—O3D1.336 (13)
C13B—C12B1.380 (6)C14D—C15D1.456 (13)
C13B—H13B0.9300C15D—C16D1.3900
C12B—C11B1.355 (6)C15D—C20D1.3900
C12B—H12B0.9300C16D—C17D1.3900
C11B—C10B1.360 (6)C16D—H16D0.9300
C11B—O3B1.396 (7)C17D—C18D1.3900
C11B—O3D1.551 (13)C17D—H17D0.9300
C10B—C9B1.376 (5)C18D—C19D1.3900
C10B—H10B0.9300C18D—H18D0.9300
C9B—H9B0.9300C19D—C20D1.3900
C2B—O1B1.236 (4)C19D—H19D0.9300
C2B—N1B1.344 (4)C20D—H20D0.9300
C2A—C1A—H1A1109.5H1B2—C1B—H1B3109.5
C2A—C1A—H1A2109.5C2A—N1A—N2A118.7 (2)
H1A1—C1A—H1A2109.5C2A—N1A—C6A124.3 (3)
C2A—C1A—H1A3109.5N2A—N1A—C6A116.3 (2)
H1A1—C1A—H1A3109.5C3A—N2A—N1A110.0 (2)
H1A2—C1A—H1A3109.5C4A—N3A—C3A125.3 (3)
O1A—C2A—N1A120.5 (3)C4A—N3A—H3A109 (2)
O1A—C2A—C1A121.6 (3)C3A—N3A—H3A125 (2)
N1A—C2A—C1A117.9 (3)C2B—N1B—N2B118.8 (3)
N1A—C6A—C7A112.8 (3)C2B—N1B—C6B123.3 (3)
N1A—C6A—C8A108.2 (2)N2B—N1B—C6B116.6 (2)
C7A—C6A—C8A115.0 (3)C3B—N2B—N1B109.9 (2)
N1A—C6A—S1A101.4 (2)C4B—N3B—C3B124.4 (3)
C7A—C6A—S1A106.6 (2)C4B—N3B—H3B122 (3)
C8A—C6A—S1A112.1 (2)C3B—N3B—H3B114 (3)
N2A—C3A—N3A119.0 (3)C3A—S1A—C6A89.90 (14)
N2A—C3A—S1A118.5 (2)C3B—S1B—C6B89.66 (14)
N3A—C3A—S1A122.5 (2)O4A—C14A—O3A110.2 (13)
O2A—C4A—N3A121.1 (3)O4A—C14A—C15A126.8 (15)
O2A—C4A—C5A124.0 (3)O3A—C14A—C15A109.7 (10)
N3A—C4A—C5A114.8 (3)C16A—C15A—C20A120.0
C4A—C5A—H5A1109.5C16A—C15A—C14A119.7 (7)
C4A—C5A—H5A2109.5C20A—C15A—C14A118.4 (8)
H5A1—C5A—H5A2109.5C15A—C16A—C17A120.0
C4A—C5A—H5A3109.5C15A—C16A—H16A120.0
H5A1—C5A—H5A3109.5C17A—C16A—H16A120.0
H5A2—C5A—H5A3109.5C18A—C17A—C16A120.0
C6A—C7A—H7A1109.5C18A—C17A—H17A120.0
C6A—C7A—H7A2109.5C16A—C17A—H17A120.0
H7A1—C7A—H7A2109.5C17A—C18A—C19A120.0
C6A—C7A—H7A3109.5C17A—C18A—H18A120.0
H7A1—C7A—H7A3109.5C19A—C18A—H18A120.0
H7A2—C7A—H7A3109.5C20A—C19A—C18A120.0
C9A—C8A—C13A117.6 (3)C20A—C19A—H19A120.0
C9A—C8A—C6A121.0 (3)C18A—C19A—H19A120.0
C13A—C8A—C6A121.1 (3)C19A—C20A—C15A120.0
C8A—C9A—C10A121.2 (4)C19A—C20A—H20A120.0
C8A—C9A—H9A119.4C15A—C20A—H20A120.0
C10A—C9A—H9A119.4C14A—O3A—C11A117.1 (8)
C11A—C10A—C9A119.2 (4)O4C—C14C—O3C111.6 (14)
C11A—C10A—H10A120.4O4C—C14C—C15C111.8 (14)
C9A—C10A—H10A120.4O3C—C14C—C15C107.0 (12)
C12A—C11A—C10A120.3 (4)C16C—C15C—C20C120.0
C12A—C11A—O3A104.9 (6)C16C—C15C—C14C109.1 (8)
C10A—C11A—O3A134.7 (6)C20C—C15C—C14C125.1 (7)
C12A—C11A—O3C136.1 (6)C15C—C16C—C17C120.0
C10A—C11A—O3C103.5 (6)C15C—C16C—H16C120.0
C13A—C12A—C11A119.7 (5)C17C—C16C—H16C120.0
C13A—C12A—H12A120.2C16C—C17C—C18C120.0
C11A—C12A—H12A120.2C16C—C17C—H17C120.0
C12A—C13A—C8A121.9 (4)C18C—C17C—H17C120.0
C12A—C13A—H13A119.0C17C—C18C—C19C120.0
C8A—C13A—H13A119.0C17C—C18C—H18C120.0
C4B—C5B—H5B1109.5C19C—C18C—H18C120.0
C4B—C5B—H5B2109.5C20C—C19C—C18C120.0
H5B1—C5B—H5B2109.5C20C—C19C—H19C120.0
C4B—C5B—H5B3109.5C18C—C19C—H19C120.0
H5B1—C5B—H5B3109.5C19C—C20C—C15C120.0
H5B2—C5B—H5B3109.5C19C—C20C—H20C120.0
O2B—C4B—N3B121.3 (3)C15C—C20C—H20C120.0
O2B—C4B—C5B122.8 (3)C14C—O3C—C11A127.5 (9)
N3B—C4B—C5B115.8 (3)O4B—C14B—O3B121.2 (8)
N2B—C3B—N3B119.3 (3)O4B—C14B—C15B125.6 (8)
N2B—C3B—S1B119.1 (2)O3B—C14B—C15B113.1 (7)
N3B—C3B—S1B121.5 (2)C16B—C15B—C20B120.0
N1B—C6B—C8B110.0 (2)C16B—C15B—C14B121.5 (8)
N1B—C6B—C7B112.3 (3)C20B—C15B—C14B118.5 (8)
C8B—C6B—C7B114.9 (3)C17B—C16B—C15B120.0
N1B—C6B—S1B102.0 (2)C17B—C16B—H16B120.0
C8B—C6B—S1B110.0 (2)C15B—C16B—H16B120.0
C7B—C6B—S1B106.8 (2)C16B—C17B—C18B120.0
C6B—C7B—H7B1109.5C16B—C17B—H17B120.0
C6B—C7B—H7B2109.5C18B—C17B—H17B120.0
H7B1—C7B—H7B2109.5C19B—C18B—C17B120.0
C6B—C7B—H7B3109.5C19B—C18B—H18B120.0
H7B1—C7B—H7B3109.5C17B—C18B—H18B120.0
H7B2—C7B—H7B3109.5C18B—C19B—C20B120.0
C13B—C8B—C9B118.3 (3)C18B—C19B—H19B120.0
C13B—C8B—C6B121.5 (3)C20B—C19B—H19B120.0
C9B—C8B—C6B120.2 (3)C19B—C20B—C15B120.0
C8B—C13B—C12B120.7 (4)C19B—C20B—H20B120.0
C8B—C13B—H13B119.6C15B—C20B—H20B120.0
C12B—C13B—H13B119.6C14B—O3B—C11B112.7 (7)
C11B—C12B—C13B119.8 (4)O4D—C14D—O3D124.1 (14)
C11B—C12B—H12B120.1O4D—C14D—C15D121.6 (14)
C13B—C12B—H12B120.1O3D—C14D—C15D114.3 (13)
C12B—C11B—C10B120.7 (4)C16D—C15D—C20D120.0
C12B—C11B—O3B118.9 (4)C16D—C15D—C14D121.3 (16)
C10B—C11B—O3B118.4 (5)C20D—C15D—C14D118.7 (16)
C12B—C11B—O3D116.0 (6)C17D—C16D—C15D120.0
C10B—C11B—O3D118.4 (6)C17D—C16D—H16D120.0
C11B—C10B—C9B119.1 (4)C15D—C16D—H16D120.0
C11B—C10B—H10B120.4C16D—C17D—C18D120.0
C9B—C10B—H10B120.4C16D—C17D—H17D120.0
C8B—C9B—C10B121.4 (3)C18D—C17D—H17D120.0
C8B—C9B—H9B119.3C19D—C18D—C17D120.0
C10B—C9B—H9B119.3C19D—C18D—H18D120.0
O1B—C2B—N1B119.7 (3)C17D—C18D—H18D120.0
O1B—C2B—C1B122.1 (3)C18D—C19D—C20D120.0
N1B—C2B—C1B118.2 (3)C18D—C19D—H19D120.0
C2B—C1B—H1B1109.5C20D—C19D—H19D120.0
C2B—C1B—H1B2109.5C19D—C20D—C15D120.0
H1B1—C1B—H1B2109.5C19D—C20D—H20D120.0
C2B—C1B—H1B3109.5C15D—C20D—H20D120.0
H1B1—C1B—H1B3109.5C14D—O3D—C11B104.3 (10)
N1A—C6A—C8A—C9A80.2 (3)N3A—C3A—S1A—C6A170.4 (3)
C7A—C6A—C8A—C9A152.7 (3)N1A—C6A—S1A—C3A15.58 (19)
S1A—C6A—C8A—C9A30.8 (3)C7A—C6A—S1A—C3A133.8 (2)
N1A—C6A—C8A—C13A94.1 (4)C8A—C6A—S1A—C3A99.6 (2)
C7A—C6A—C8A—C13A33.0 (4)N2B—C3B—S1B—C6B9.2 (3)
S1A—C6A—C8A—C13A155.0 (3)N3B—C3B—S1B—C6B169.8 (3)
C13A—C8A—C9A—C10A1.2 (5)N1B—C6B—S1B—C3B13.5 (2)
C6A—C8A—C9A—C10A175.7 (3)C8B—C6B—S1B—C3B103.2 (2)
C8A—C9A—C10A—C11A1.4 (6)C7B—C6B—S1B—C3B131.5 (2)
C9A—C10A—C11A—C12A1.2 (6)O4A—C14A—C15A—C16A68 (2)
C9A—C10A—C11A—O3A177.2 (7)O3A—C14A—C15A—C16A155.3 (9)
C9A—C10A—C11A—O3C178.7 (5)O4A—C14A—C15A—C20A96 (2)
C10A—C11A—C12A—C13A0.8 (7)O3A—C14A—C15A—C20A40.2 (14)
O3A—C11A—C12A—C13A177.9 (6)C20A—C15A—C16A—C17A0.0
O3C—C11A—C12A—C13A177.4 (7)C14A—C15A—C16A—C17A164.3 (10)
C11A—C12A—C13A—C8A0.7 (7)C15A—C16A—C17A—C18A0.0
C9A—C8A—C13A—C12A0.9 (6)C16A—C17A—C18A—C19A0.0
C6A—C8A—C13A—C12A175.4 (4)C17A—C18A—C19A—C20A0.0
N1B—C6B—C8B—C13B148.5 (4)C18A—C19A—C20A—C15A0.0
C7B—C6B—C8B—C13B20.6 (5)C16A—C15A—C20A—C19A0.0
S1B—C6B—C8B—C13B100.0 (4)C14A—C15A—C20A—C19A164.5 (9)
N1B—C6B—C8B—C9B33.4 (4)O4A—C14A—O3A—C11A41 (2)
C7B—C6B—C8B—C9B161.2 (3)C15A—C14A—O3A—C11A174.9 (9)
S1B—C6B—C8B—C9B78.1 (4)C12A—C11A—O3A—C14A143.6 (10)
C9B—C8B—C13B—C12B2.2 (7)C10A—C11A—O3A—C14A40.0 (14)
C6B—C8B—C13B—C12B175.9 (5)O4C—C14C—C15C—C16C175.6 (14)
C8B—C13B—C12B—C11B1.7 (9)O3C—C14C—C15C—C16C61.9 (14)
C13B—C12B—C11B—C10B0.7 (10)O4C—C14C—C15C—C20C23 (2)
C13B—C12B—C11B—O3B164.8 (6)O3C—C14C—C15C—C20C145.4 (9)
C13B—C12B—C11B—O3D154.3 (7)C20C—C15C—C16C—C17C0.0
C12B—C11B—C10B—C9B0.3 (8)C14C—C15C—C16C—C17C154.3 (10)
O3B—C11B—C10B—C9B164.5 (5)C15C—C16C—C17C—C18C0.0
O3D—C11B—C10B—C9B154.2 (6)C16C—C17C—C18C—C19C0.0
C13B—C8B—C9B—C10B1.8 (6)C17C—C18C—C19C—C20C0.0
C6B—C8B—C9B—C10B176.4 (4)C18C—C19C—C20C—C15C0.0
C11B—C10B—C9B—C8B0.8 (7)C16C—C15C—C20C—C19C0.0
O1A—C2A—N1A—N2A175.8 (3)C14C—C15C—C20C—C19C149.9 (12)
C1A—C2A—N1A—N2A5.0 (4)O4C—C14C—O3C—C11A29 (2)
O1A—C2A—N1A—C6A5.8 (5)C15C—C14C—O3C—C11A151.5 (11)
C1A—C2A—N1A—C6A175.1 (3)C12A—C11A—O3C—C14C132.4 (13)
C7A—C6A—N1A—C2A55.1 (4)C10A—C11A—O3C—C14C50.7 (15)
C8A—C6A—N1A—C2A73.2 (4)O4B—C14B—C15B—C16B175.2 (9)
S1A—C6A—N1A—C2A168.7 (2)O3B—C14B—C15B—C16B8.9 (10)
C7A—C6A—N1A—N2A134.7 (3)O4B—C14B—C15B—C20B3.8 (13)
C8A—C6A—N1A—N2A97.0 (3)O3B—C14B—C15B—C20B172.2 (6)
S1A—C6A—N1A—N2A21.0 (3)C20B—C15B—C16B—C17B0.0
N3A—C3A—N2A—N1A178.5 (2)C14B—C15B—C16B—C17B178.9 (8)
S1A—C3A—N2A—N1A1.5 (3)C15B—C16B—C17B—C18B0.0
C2A—N1A—N2A—C3A173.3 (3)C16B—C17B—C18B—C19B0.0
C6A—N1A—N2A—C3A15.9 (3)C17B—C18B—C19B—C20B0.0
O2A—C4A—N3A—C3A3.5 (5)C18B—C19B—C20B—C15B0.0
C5A—C4A—N3A—C3A175.3 (3)C16B—C15B—C20B—C19B0.0
N2A—C3A—N3A—C4A175.4 (3)C14B—C15B—C20B—C19B178.9 (7)
S1A—C3A—N3A—C4A4.6 (4)O4B—C14B—O3B—C11B4.4 (12)
O1B—C2B—N1B—N2B175.6 (3)C15B—C14B—O3B—C11B179.4 (6)
C1B—C2B—N1B—N2B3.8 (5)C12B—C11B—O3B—C14B110.0 (7)
O1B—C2B—N1B—C6B8.8 (5)C10B—C11B—O3B—C14B85.6 (8)
C1B—C2B—N1B—C6B170.5 (3)O4D—C14D—C15D—C16D5 (2)
C8B—C6B—N1B—C2B67.7 (4)O3D—C14D—C15D—C16D173.9 (11)
C7B—C6B—N1B—C2B61.6 (4)O4D—C14D—C15D—C20D175.6 (14)
S1B—C6B—N1B—C2B175.6 (3)O3D—C14D—C15D—C20D5.3 (17)
C8B—C6B—N1B—N2B99.4 (3)C20D—C15D—C16D—C17D0.0
C7B—C6B—N1B—N2B131.4 (3)C14D—C15D—C16D—C17D179.2 (15)
S1B—C6B—N1B—N2B17.4 (3)C15D—C16D—C17D—C18D0.0
N3B—C3B—N2B—N1B178.7 (3)C16D—C17D—C18D—C19D0.0
S1B—C3B—N2B—N1B0.3 (3)C17D—C18D—C19D—C20D0.0
C2B—N1B—N2B—C3B179.9 (3)C18D—C19D—C20D—C15D0.0
C6B—N1B—N2B—C3B12.3 (4)C16D—C15D—C20D—C19D0.0
O2B—C4B—N3B—C3B4.4 (5)C14D—C15D—C20D—C19D179.2 (15)
C5B—C4B—N3B—C3B174.5 (3)O4D—C14D—O3D—C11B4.6 (19)
N2B—C3B—N3B—C4B171.1 (3)C15D—C14D—O3D—C11B176.4 (11)
S1B—C3B—N3B—C4B10.0 (4)C12B—C11B—O3D—C14D110.4 (10)
N2A—C3A—S1A—C6A9.6 (2)C10B—C11B—O3D—C14D94.0 (10)
Hydrogen-bond geometry (Å, º) top
Cg2, Cg3 and Cg6 are the centroids of the C8A–C13A, C15A–C20A and C8B–C13B rings, respectively.
D—H···AD—HH···AD···AD—H···A
N3A—H3A···O1Bi0.84 (4)1.96 (3)2.792 (4)175 (3)
N3B—H3B···O1A0.84 (4)1.99 (5)2.801 (4)163 (4)
C5A—H5A2···O1Bi0.962.593.226 (5)124
C7A—H7A2···O2Aii0.962.543.482 (5)168
C9B—H9B···O2Biii0.932.583.303 (5)135
C5B—H5B1···O4Aiv0.962.593.50 (2)158
C5B—H5B1···O4Civ0.962.453.395 (17)166
C12A—H12A···O4Civ0.932.583.211 (15)125
C17B—H17B···Cg2v0.932.913.664 (8)139
C17C—H17C···Cg6v0.932.983.776 (10)145
C20C—H20C···Cg3vi0.932.643.521 (11)159
Symmetry codes: (i) x+1, y+1, z; (ii) x, y, z; (iii) x+1, y, z; (iv) x1, y, z; (v) x+1, y+1, z+1; (vi) x+2, y+1, z+1.
4-(5-Acetamido-3-acetyl-2-methyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)phenyl 2-methylpropanoate 0.25-hydrate (II) top
Crystal data top
C17H21N3O4S·0.25H2OZ = 4
Mr = 367.93F(000) = 778
Triclinic, P1Dx = 1.307 Mg m3
a = 6.7802 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 17.2671 (4) ÅCell parameters from 7680 reflections
c = 17.3089 (4) Åθ = 2.4–25.5°
α = 108.224 (1)°µ = 0.20 mm1
β = 99.084 (1)°T = 293 K
γ = 96.720 (1)°BLOCK, colourless
V = 1870.50 (7) Å30.30 × 0.25 × 0.20 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer
7680 independent reflections
Radiation source: fine-focus sealed tube5737 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
ω and φ scansθmax = 26.5°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 78
Tmin = 0.660, Tmax = 0.746k = 2121
27060 measured reflectionsl = 2121
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: mixed
wR(F2) = 0.169H 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 parametersΔρmax = 0.48 e Å3
242 restraintsΔρmin = 0.38 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10B0.6406 (7)0.1228 (2)0.0560 (2)0.1066 (13)
H10B0.65210.07670.01240.128*
C11B0.4800 (6)0.1636 (3)0.0486 (2)0.1023 (12)
C12B0.4677 (5)0.2347 (2)0.1099 (2)0.0826 (9)
H12B0.36200.26330.10300.099*
C13B0.6142 (4)0.26296 (18)0.18174 (17)0.0650 (7)
H13B0.60940.31230.22270.078*
C1B0.6525 (4)0.36366 (16)0.43978 (17)0.0646 (7)
H1B10.57390.39160.40950.097*
H1B20.76890.40200.47660.097*
H1B30.57090.34220.47150.097*
C1A0.7780 (4)0.59164 (14)0.45336 (16)0.0571 (6)
H1A10.81510.53790.43470.086*
H1A20.63340.58650.43820.086*
H1A30.82070.61540.51270.086*
C2A0.8791 (4)0.64657 (13)0.41369 (14)0.0474 (5)
C2B0.7206 (4)0.29410 (15)0.38025 (15)0.0528 (6)
C3A0.7214 (3)0.82955 (12)0.50833 (13)0.0411 (5)
C3B1.0722 (3)0.40326 (13)0.31134 (13)0.0420 (5)
C4A0.6056 (4)0.95076 (14)0.59064 (16)0.0562 (6)
C4B1.3254 (4)0.49275 (15)0.27918 (15)0.0517 (5)
C5A0.4525 (5)0.97664 (17)0.6418 (2)0.0774 (8)
H5A10.49901.03260.67870.116*
H5A20.43390.94070.67360.116*
H5A30.32590.97320.60600.116*
C5B1.3775 (4)0.57778 (17)0.27520 (19)0.0656 (7)
H5B11.51520.58700.26850.098*
H5B21.36270.61810.32570.098*
H5B31.28800.58280.22890.098*
C6B0.9311 (4)0.25124 (13)0.27334 (14)0.0477 (5)
C6A0.9260 (3)0.78654 (13)0.39637 (14)0.0440 (5)
C7A1.1542 (4)0.79518 (16)0.40080 (18)0.0608 (6)
H7A11.22270.80520.45690.091*
H7A21.19970.84070.38360.091*
H7A31.18390.74500.36480.091*
C7B1.0076 (5)0.18272 (16)0.30150 (18)0.0659 (7)
H7B11.09120.20660.35630.099*
H7B21.08580.15420.26370.099*
H7B30.89400.14430.30220.099*
C8B0.7685 (4)0.21984 (14)0.19451 (15)0.0530 (6)
C8A0.7970 (3)0.76385 (13)0.30896 (13)0.0435 (5)
C9A0.8586 (4)0.71431 (17)0.23993 (16)0.0621 (6)
H9A0.98340.69730.24650.075*
C9B0.7846 (6)0.1514 (2)0.1291 (2)0.0855 (10)
H9B0.89400.12440.13460.103*
C10A0.7363 (5)0.69025 (18)0.16185 (17)0.0704 (8)
H10A0.77980.65760.11610.085*
C11A0.5527 (4)0.71394 (18)0.15148 (16)0.0634 (7)
C12A0.4859 (4)0.76212 (17)0.21818 (16)0.0623 (6)
H12A0.35990.77810.21080.075*
C13A0.6080 (4)0.78648 (15)0.29646 (15)0.0523 (5)
H13A0.56260.81880.34180.063*
C14A0.2528 (5)0.6466 (2)0.04872 (17)0.0773 (9)
C15A0.1621 (6)0.6282 (2)0.04174 (18)0.0909 (11)
H15A0.20160.67770.05590.109*
C17A0.2475 (9)0.5587 (3)0.0944 (3)0.1381 (18)
H17D0.19830.50810.08600.207*
H17E0.39300.57070.07890.207*
H17F0.20590.55280.15190.207*
C16A0.0658 (7)0.6106 (3)0.0561 (2)0.1227 (16)
H16D0.12250.60190.11320.184*
H16E0.11230.65670.02090.184*
H16F0.10810.56180.04320.184*
N1B0.8656 (3)0.31381 (11)0.34072 (11)0.0465 (4)
N1A0.8489 (3)0.72603 (10)0.43526 (11)0.0431 (4)
N2A0.7133 (3)0.75104 (10)0.48764 (11)0.0432 (4)
N2B0.9297 (3)0.39715 (11)0.35052 (11)0.0442 (4)
N3B1.1558 (3)0.47934 (11)0.31041 (11)0.0463 (4)
H3B1.09840.52090.33050.056*
N3A0.6051 (3)0.86705 (11)0.56172 (11)0.0462 (4)
H3A0.52580.83590.57840.055*
O1B0.6499 (3)0.22122 (11)0.36685 (13)0.0733 (6)
O1A0.9864 (3)0.62179 (10)0.36345 (12)0.0633 (5)
O2A0.7210 (4)0.99870 (11)0.57378 (15)0.0877 (7)
O2B1.4220 (3)0.43814 (12)0.25612 (14)0.0745 (5)
O3A0.4407 (4)0.69246 (15)0.07026 (11)0.0851 (7)
O4A0.1729 (4)0.62528 (18)0.09728 (14)0.1077 (9)
S1A0.88298 (9)0.88522 (3)0.46752 (4)0.04905 (17)
S1B1.15307 (10)0.31302 (4)0.25781 (4)0.05540 (19)
C14B0.1788 (9)0.0980 (5)0.0412 (4)0.1041 (19)0.723 (5)
C15B0.0485 (11)0.0684 (5)0.1256 (5)0.097 (2)0.723 (5)
H15B0.03770.01590.13310.117*0.723 (5)
C16B0.0847 (12)0.1334 (5)0.1207 (5)0.143 (3)0.723 (5)
H16A0.17650.11990.17320.214*0.723 (5)
H16B0.16090.13500.07810.214*0.723 (5)
H16C0.00150.18660.10770.214*0.723 (5)
C17B0.1577 (13)0.0551 (5)0.1955 (4)0.115 (2)0.723 (5)
H17A0.06090.03610.24730.173*0.723 (5)
H17B0.24080.10620.19010.173*0.723 (5)
H17C0.24170.01430.19430.173*0.723 (5)
O3B0.3507 (7)0.1413 (3)0.0316 (3)0.1161 (16)0.723 (5)
O4B0.1403 (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)
H15'0.03000.14830.12570.140*0.277 (5)
C16'0.155 (3)0.0433 (17)0.1396 (14)0.177 (8)0.277 (5)
H16G0.18700.05650.08530.266*0.277 (5)
H16H0.25560.05820.17550.266*0.277 (5)
H16I0.15510.01500.16190.266*0.277 (5)
C17'0.054 (4)0.0580 (17)0.2240 (12)0.138 (8)0.277 (5)
H17G0.08140.05080.25500.208*0.277 (5)
H17H0.14330.09580.23880.208*0.277 (5)
H17I0.09850.00550.23650.208*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)
O10.348 (3)0.0897 (8)0.1929 (9)0.240 (5)*0.5
H1A0.36 (3)0.138 (5)0.231 (7)0.288*0.5
H1B0.33 (3)0.100 (10)0.146 (5)0.288*0.5
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10B0.116 (3)0.092 (3)0.081 (2)0.028 (2)0.005 (2)0.0110 (19)
C11B0.090 (3)0.110 (3)0.073 (2)0.010 (2)0.0138 (18)0.001 (2)
C12B0.0668 (19)0.102 (2)0.0749 (19)0.0302 (17)0.0075 (15)0.0218 (18)
C13B0.0642 (16)0.0689 (17)0.0586 (15)0.0225 (13)0.0118 (12)0.0135 (13)
C1B0.0747 (17)0.0555 (15)0.0730 (17)0.0097 (13)0.0389 (14)0.0239 (13)
C1A0.0748 (16)0.0351 (11)0.0678 (15)0.0116 (11)0.0221 (13)0.0220 (11)
C2A0.0535 (13)0.0343 (11)0.0538 (12)0.0069 (9)0.0090 (11)0.0157 (9)
C2B0.0623 (15)0.0467 (13)0.0574 (13)0.0080 (11)0.0211 (11)0.0249 (11)
C3A0.0437 (11)0.0347 (10)0.0442 (11)0.0033 (8)0.0052 (9)0.0153 (8)
C3B0.0472 (12)0.0401 (11)0.0413 (10)0.0118 (9)0.0097 (9)0.0157 (9)
C4A0.0701 (16)0.0366 (12)0.0609 (14)0.0078 (11)0.0166 (12)0.0142 (10)
C4B0.0469 (13)0.0553 (14)0.0533 (13)0.0037 (11)0.0098 (10)0.0210 (11)
C5A0.099 (2)0.0481 (15)0.092 (2)0.0249 (15)0.0407 (18)0.0182 (14)
C5B0.0621 (16)0.0624 (16)0.0813 (18)0.0029 (12)0.0224 (14)0.0360 (14)
C6B0.0559 (13)0.0365 (11)0.0554 (13)0.0132 (10)0.0182 (10)0.0172 (10)
C6A0.0427 (11)0.0345 (10)0.0570 (12)0.0038 (8)0.0137 (10)0.0180 (9)
C7A0.0438 (13)0.0513 (14)0.0886 (18)0.0026 (10)0.0184 (12)0.0252 (13)
C7B0.0865 (19)0.0470 (14)0.0730 (17)0.0270 (13)0.0168 (14)0.0268 (12)
C8B0.0578 (14)0.0434 (12)0.0559 (13)0.0124 (10)0.0138 (11)0.0119 (10)
C8A0.0469 (12)0.0365 (10)0.0525 (12)0.0031 (9)0.0166 (10)0.0207 (9)
C9A0.0616 (15)0.0651 (16)0.0653 (16)0.0164 (12)0.0255 (13)0.0219 (13)
C9B0.093 (2)0.0699 (19)0.076 (2)0.0291 (17)0.0075 (17)0.0004 (16)
C10A0.086 (2)0.0720 (18)0.0532 (15)0.0108 (15)0.0282 (14)0.0155 (13)
C11A0.0727 (18)0.0674 (16)0.0514 (14)0.0018 (13)0.0130 (12)0.0269 (12)
C12A0.0606 (15)0.0692 (17)0.0592 (15)0.0112 (13)0.0083 (12)0.0267 (13)
C13A0.0548 (14)0.0513 (13)0.0532 (13)0.0116 (11)0.0147 (11)0.0186 (10)
C14A0.095 (2)0.081 (2)0.0536 (15)0.0028 (17)0.0060 (15)0.0302 (15)
C15A0.117 (3)0.092 (2)0.0532 (16)0.005 (2)0.0021 (17)0.0273 (16)
C17A0.174 (5)0.154 (5)0.076 (3)0.041 (4)0.028 (3)0.019 (3)
C16A0.130 (4)0.154 (4)0.071 (2)0.014 (3)0.008 (2)0.039 (2)
N1B0.0592 (11)0.0358 (9)0.0488 (10)0.0088 (8)0.0192 (9)0.0160 (8)
N1A0.0471 (10)0.0328 (9)0.0525 (10)0.0058 (7)0.0130 (8)0.0180 (8)
N2A0.0491 (10)0.0340 (9)0.0493 (10)0.0057 (7)0.0127 (8)0.0173 (8)
N2B0.0555 (11)0.0366 (9)0.0461 (9)0.0097 (8)0.0189 (8)0.0171 (8)
N3B0.0512 (11)0.0400 (10)0.0536 (10)0.0098 (8)0.0201 (8)0.0188 (8)
N3A0.0525 (11)0.0343 (9)0.0537 (10)0.0056 (8)0.0151 (8)0.0164 (8)
O1B0.0928 (14)0.0464 (10)0.0925 (14)0.0058 (9)0.0455 (11)0.0293 (9)
O1A0.0766 (12)0.0427 (9)0.0826 (12)0.0184 (8)0.0391 (10)0.0242 (8)
O2A0.1157 (17)0.0349 (9)0.1144 (17)0.0019 (10)0.0567 (14)0.0157 (10)
O2B0.0606 (11)0.0644 (12)0.1115 (16)0.0192 (9)0.0414 (11)0.0334 (11)
O3A0.0955 (16)0.1057 (17)0.0484 (10)0.0107 (13)0.0080 (10)0.0317 (11)
O4A0.1061 (19)0.139 (2)0.0681 (14)0.0272 (16)0.0003 (13)0.0480 (15)
S1A0.0540 (3)0.0317 (3)0.0599 (3)0.0010 (2)0.0144 (3)0.0152 (2)
S1B0.0551 (4)0.0462 (3)0.0695 (4)0.0163 (3)0.0258 (3)0.0170 (3)
C14B0.076 (3)0.140 (5)0.077 (3)0.007 (3)0.012 (3)0.016 (3)
C15B0.087 (4)0.096 (5)0.092 (4)0.003 (3)0.015 (3)0.031 (3)
C16B0.119 (5)0.144 (6)0.183 (7)0.049 (5)0.010 (5)0.080 (5)
C17B0.143 (7)0.097 (4)0.082 (4)0.004 (5)0.015 (4)0.010 (3)
O3B0.096 (3)0.168 (4)0.060 (2)0.020 (3)0.009 (2)0.033 (2)
O4B0.118 (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)
Geometric parameters (Å, º) top
C10B—C11B1.375 (5)C8A—C13A1.387 (3)
C10B—C9B1.381 (5)C8A—C9A1.391 (3)
C10B—H10B0.9300C9A—C10A1.379 (4)
C11B—C12B1.370 (5)C9A—H9A0.9300
C11B—O3B1.430 (5)C9B—H9B0.9300
C11B—O3B'1.476 (11)C10A—C11A1.357 (4)
C12B—C13B1.374 (4)C10A—H10A0.9300
C12B—H12B0.9300C11A—C12A1.373 (4)
C13B—C8B1.382 (4)C11A—O3A1.401 (3)
C13B—H13B0.9300C12A—C13A1.381 (3)
C1B—C2B1.491 (3)C12A—H12A0.9300
C1B—H1B10.9600C13A—H13A0.9300
C1B—H1B20.9600C14A—O4A1.195 (4)
C1B—H1B30.9600C14A—O3A1.348 (4)
C1A—C2A1.498 (3)C14A—C15A1.507 (4)
C1A—H1A10.9600C15A—C17A1.501 (6)
C1A—H1A20.9600C15A—C16A1.505 (6)
C1A—H1A30.9600C15A—H15A0.9800
C2A—O1A1.228 (3)C17A—H17D0.9600
C2A—N1A1.354 (3)C17A—H17E0.9600
C2B—O1B1.228 (3)C17A—H17F0.9600
C2B—N1B1.353 (3)C16A—H16D0.9600
C3A—N2A1.281 (3)C16A—H16E0.9600
C3A—N3A1.368 (3)C16A—H16F0.9600
C3A—S1A1.745 (2)N1B—N2B1.402 (2)
C3B—N2B1.278 (3)N1A—N2A1.401 (2)
C3B—N3B1.374 (3)N3B—H3B0.8600
C3B—S1B1.745 (2)N3A—H3A0.8600
C4A—O2A1.206 (3)C14B—O4B1.209 (8)
C4A—N3A1.373 (3)C14B—O3B1.266 (7)
C4A—C5A1.487 (4)C14B—C15B1.482 (8)
C4B—O2B1.212 (3)C15B—C17B1.487 (9)
C4B—N3B1.372 (3)C15B—C16B1.511 (9)
C4B—C5B1.495 (4)C15B—H15B0.9800
C5A—H5A10.9600C16B—H16A0.9600
C5A—H5A20.9600C16B—H16B0.9600
C5A—H5A30.9600C16B—H16C0.9600
C5B—H5B10.9600C17B—H17A0.9600
C5B—H5B20.9600C17B—H17B0.9600
C5B—H5B30.9600C17B—H17C0.9600
C6B—N1B1.487 (3)C14'—O4B'1.212 (15)
C6B—C8B1.514 (3)C14'—O3B'1.256 (14)
C6B—C7B1.527 (3)C14'—C15'1.522 (16)
C6B—S1B1.846 (2)C15'—C17'1.491 (15)
C6A—N1A1.497 (3)C15'—C16'1.544 (16)
C6A—C7A1.524 (3)C15'—H15'0.9800
C6A—C8A1.529 (3)C16'—H16G0.9600
C6A—S1A1.850 (2)C16'—H16H0.9600
C7A—H7A10.9600C16'—H16I0.9600
C7A—H7A20.9600C17'—H17G0.9600
C7A—H7A30.9600C17'—H17H0.9600
C7B—H7B10.9600C17'—H17I0.9600
C7B—H7B20.9600O1—H1A0.87 (2)
C7B—H7B30.9600O1—H1B0.88 (2)
C8B—C9B1.386 (4)
C11B—C10B—C9B118.8 (3)C9A—C10A—H10A119.9
C11B—C10B—H10B120.6C10A—C11A—C12A120.8 (2)
C9B—C10B—H10B120.6C10A—C11A—O3A117.9 (3)
C12B—C11B—C10B121.3 (3)C12A—C11A—O3A121.2 (3)
C12B—C11B—O3B119.4 (4)C11A—C12A—C13A119.1 (3)
C10B—C11B—O3B117.8 (4)C11A—C12A—H12A120.4
C12B—C11B—O3B'110.3 (7)C13A—C12A—H12A120.4
C10B—C11B—O3B'122.6 (8)C12A—C13A—C8A121.5 (2)
C11B—C12B—C13B118.9 (3)C12A—C13A—H13A119.3
C11B—C12B—H12B120.5C8A—C13A—H13A119.3
C13B—C12B—H12B120.5O4A—C14A—O3A122.5 (3)
C12B—C13B—C8B121.5 (3)O4A—C14A—C15A126.2 (3)
C12B—C13B—H13B119.2O3A—C14A—C15A111.3 (3)
C8B—C13B—H13B119.2C17A—C15A—C16A112.9 (4)
C2B—C1B—H1B1109.5C17A—C15A—C14A109.7 (3)
C2B—C1B—H1B2109.5C16A—C15A—C14A110.0 (3)
H1B1—C1B—H1B2109.5C17A—C15A—H15A108.0
C2B—C1B—H1B3109.5C16A—C15A—H15A108.0
H1B1—C1B—H1B3109.5C14A—C15A—H15A108.0
H1B2—C1B—H1B3109.5C15A—C17A—H17D109.5
C2A—C1A—H1A1109.5C15A—C17A—H17E109.5
C2A—C1A—H1A2109.5H17D—C17A—H17E109.5
H1A1—C1A—H1A2109.5C15A—C17A—H17F109.5
C2A—C1A—H1A3109.5H17D—C17A—H17F109.5
H1A1—C1A—H1A3109.5H17E—C17A—H17F109.5
H1A2—C1A—H1A3109.5C15A—C16A—H16D109.5
O1A—C2A—N1A120.2 (2)C15A—C16A—H16E109.5
O1A—C2A—C1A122.3 (2)H16D—C16A—H16E109.5
N1A—C2A—C1A117.5 (2)C15A—C16A—H16F109.5
O1B—C2B—N1B120.3 (2)H16D—C16A—H16F109.5
O1B—C2B—C1B122.2 (2)H16E—C16A—H16F109.5
N1B—C2B—C1B117.5 (2)C2B—N1B—N2B119.31 (18)
N2A—C3A—N3A119.36 (19)C2B—N1B—C6B122.96 (18)
N2A—C3A—S1A118.46 (17)N2B—N1B—C6B116.47 (16)
N3A—C3A—S1A122.18 (15)C2A—N1A—N2A119.05 (17)
N2B—C3B—N3B120.21 (19)C2A—N1A—C6A123.88 (18)
N2B—C3B—S1B118.48 (16)N2A—N1A—C6A116.36 (16)
N3B—C3B—S1B121.29 (16)C3A—N2A—N1A110.01 (17)
O2A—C4A—N3A121.3 (2)C3B—N2B—N1B109.86 (17)
O2A—C4A—C5A123.4 (2)C4B—N3B—C3B123.7 (2)
N3A—C4A—C5A115.3 (2)C4B—N3B—H3B118.1
O2B—C4B—N3B121.1 (2)C3B—N3B—H3B118.1
O2B—C4B—C5B123.8 (2)C3A—N3A—C4A124.8 (2)
N3B—C4B—C5B115.2 (2)C3A—N3A—H3A117.6
C4A—C5A—H5A1109.5C4A—N3A—H3A117.6
C4A—C5A—H5A2109.5C14A—O3A—C11A119.9 (2)
H5A1—C5A—H5A2109.5C3A—S1A—C6A89.58 (10)
C4A—C5A—H5A3109.5C3B—S1B—C6B89.29 (10)
H5A1—C5A—H5A3109.5O4B—C14B—O3B119.7 (6)
H5A2—C5A—H5A3109.5O4B—C14B—C15B122.5 (7)
C4B—C5B—H5B1109.5O3B—C14B—C15B116.8 (6)
C4B—C5B—H5B2109.5C14B—C15B—C17B115.7 (6)
H5B1—C5B—H5B2109.5C14B—C15B—C16B102.7 (6)
C4B—C5B—H5B3109.5C17B—C15B—C16B113.7 (7)
H5B1—C5B—H5B3109.5C14B—C15B—H15B108.1
H5B2—C5B—H5B3109.5C17B—C15B—H15B108.1
N1B—C6B—C8B111.11 (18)C16B—C15B—H15B108.1
N1B—C6B—C7B112.30 (19)C15B—C16B—H16A109.5
C8B—C6B—C7B114.0 (2)C15B—C16B—H16B109.5
N1B—C6B—S1B101.72 (14)H16A—C16B—H16B109.5
C8B—C6B—S1B109.87 (16)C15B—C16B—H16C109.5
C7B—C6B—S1B107.00 (18)H16A—C16B—H16C109.5
N1A—C6A—C7A112.66 (18)H16B—C16B—H16C109.5
N1A—C6A—C8A108.50 (16)C15B—C17B—H17A109.5
C7A—C6A—C8A114.9 (2)C15B—C17B—H17B109.5
N1A—C6A—S1A101.53 (14)H17A—C17B—H17B109.5
C7A—C6A—S1A106.51 (15)C15B—C17B—H17C109.5
C8A—C6A—S1A111.94 (15)H17A—C17B—H17C109.5
C6A—C7A—H7A1109.5H17B—C17B—H17C109.5
C6A—C7A—H7A2109.5C14B—O3B—C11B115.8 (5)
H7A1—C7A—H7A2109.5O4B'—C14'—O3B'117.3 (15)
C6A—C7A—H7A3109.5O4B'—C14'—C15'122.0 (15)
H7A1—C7A—H7A3109.5O3B'—C14'—C15'120.7 (16)
H7A2—C7A—H7A3109.5C17'—C15'—C14'115.4 (17)
C6B—C7B—H7B1109.5C17'—C15'—C16'95.1 (17)
C6B—C7B—H7B2109.5C14'—C15'—C16'134 (2)
H7B1—C7B—H7B2109.5C17'—C15'—H15'102.9
C6B—C7B—H7B3109.5C14'—C15'—H15'102.9
H7B1—C7B—H7B3109.5C16'—C15'—H15'102.9
H7B2—C7B—H7B3109.5C15'—C16'—H16G109.5
C13B—C8B—C9B118.0 (3)C15'—C16'—H16H109.5
C13B—C8B—C6B121.6 (2)H16G—C16'—H16H109.5
C9B—C8B—C6B120.0 (2)C15'—C16'—H16I109.5
C13A—C8A—C9A117.7 (2)H16G—C16'—H16I109.5
C13A—C8A—C6A121.2 (2)H16H—C16'—H16I109.5
C9A—C8A—C6A120.9 (2)C15'—C17'—H17G109.5
C10A—C9A—C8A120.6 (3)C15'—C17'—H17H109.5
C10A—C9A—H9A119.7H17G—C17'—H17H109.5
C8A—C9A—H9A119.7C15'—C17'—H17I109.5
C10B—C9B—C8B121.1 (3)H17G—C17'—H17I109.5
C10B—C9B—H9B119.5H17H—C17'—H17I109.5
C8B—C9B—H9B119.5C14'—O3B'—C11B111.7 (12)
C11A—C10A—C9A120.3 (3)H1A—O1—H1B105 (3)
C11A—C10A—H10A119.9
C9B—C10B—C11B—C12B4.3 (7)C7A—C6A—N1A—C2A54.8 (3)
C9B—C10B—C11B—O3B170.4 (4)C8A—C6A—N1A—C2A73.6 (2)
C9B—C10B—C11B—O3B'146.4 (7)S1A—C6A—N1A—C2A168.36 (17)
C10B—C11B—C12B—C13B3.3 (7)C7A—C6A—N1A—N2A134.9 (2)
O3B—C11B—C12B—C13B169.1 (4)C8A—C6A—N1A—N2A96.7 (2)
O3B'—C11B—C12B—C13B150.6 (7)S1A—C6A—N1A—N2A21.4 (2)
C11B—C12B—C13B—C8B2.4 (5)N3A—C3A—N2A—N1A177.87 (17)
C12B—C13B—C8B—C9B6.7 (5)S1A—C3A—N2A—N1A1.7 (2)
C12B—C13B—C8B—C6B179.5 (3)C2A—N1A—N2A—C3A172.95 (19)
N1B—C6B—C8B—C13B18.3 (3)C6A—N1A—N2A—C3A16.3 (2)
C7B—C6B—C8B—C13B146.5 (3)N3B—C3B—N2B—N1B178.38 (18)
S1B—C6B—C8B—C13B93.5 (3)S1B—C3B—N2B—N1B0.3 (2)
N1B—C6B—C8B—C9B169.0 (3)C2B—N1B—N2B—C3B177.4 (2)
C7B—C6B—C8B—C9B40.9 (3)C6B—N1B—N2B—C3B15.1 (3)
S1B—C6B—C8B—C9B79.2 (3)O2B—C4B—N3B—C3B5.9 (4)
N1A—C6A—C8A—C13A80.1 (2)C5B—C4B—N3B—C3B173.3 (2)
C7A—C6A—C8A—C13A152.8 (2)N2B—C3B—N3B—C4B171.3 (2)
S1A—C6A—C8A—C13A31.1 (2)S1B—C3B—N3B—C4B10.1 (3)
N1A—C6A—C8A—C9A94.9 (2)N2A—C3A—N3A—C4A177.7 (2)
C7A—C6A—C8A—C9A32.2 (3)S1A—C3A—N3A—C4A1.9 (3)
S1A—C6A—C8A—C9A153.89 (19)O2A—C4A—N3A—C3A4.3 (4)
C13A—C8A—C9A—C10A1.2 (4)C5A—C4A—N3A—C3A174.5 (2)
C6A—C8A—C9A—C10A176.4 (2)O4A—C14A—O3A—C11A2.6 (5)
C11B—C10B—C9B—C8B0.3 (6)C15A—C14A—O3A—C11A178.1 (3)
C13B—C8B—C9B—C10B5.6 (5)C10A—C11A—O3A—C14A121.9 (3)
C6B—C8B—C9B—C10B178.5 (3)C12A—C11A—O3A—C14A62.3 (4)
C8A—C9A—C10A—C11A0.7 (4)N2A—C3A—S1A—C6A9.51 (18)
C9A—C10A—C11A—C12A0.1 (4)N3A—C3A—S1A—C6A170.93 (18)
C9A—C10A—C11A—O3A175.8 (2)N1A—C6A—S1A—C3A15.74 (14)
C10A—C11A—C12A—C13A0.1 (4)C7A—C6A—S1A—C3A133.82 (17)
O3A—C11A—C12A—C13A175.5 (2)C8A—C6A—S1A—C3A99.82 (15)
C11A—C12A—C13A—C8A0.5 (4)N2B—C3B—S1B—C6B11.17 (18)
C9A—C8A—C13A—C12A1.1 (3)N3B—C3B—S1B—C6B167.47 (18)
C6A—C8A—C13A—C12A176.2 (2)N1B—C6B—S1B—C3B16.53 (14)
O4A—C14A—C15A—C17A101.7 (5)C8B—C6B—S1B—C3B101.25 (16)
O3A—C14A—C15A—C17A79.1 (4)C7B—C6B—S1B—C3B134.49 (17)
O4A—C14A—C15A—C16A23.1 (6)O4B—C14B—C15B—C17B139.6 (8)
O3A—C14A—C15A—C16A156.1 (3)O3B—C14B—C15B—C17B29.2 (10)
O1B—C2B—N1B—N2B173.7 (2)O4B—C14B—C15B—C16B95.9 (9)
C1B—C2B—N1B—N2B6.5 (3)O3B—C14B—C15B—C16B95.3 (8)
O1B—C2B—N1B—C6B7.0 (4)O4B—C14B—O3B—C11B6.2 (10)
C1B—C2B—N1B—C6B173.2 (2)C15B—C14B—O3B—C11B175.3 (6)
C8B—C6B—N1B—C2B71.5 (3)C12B—C11B—O3B—C14B88.4 (7)
C7B—C6B—N1B—C2B57.5 (3)C10B—C11B—O3B—C14B105.3 (6)
S1B—C6B—N1B—C2B171.57 (18)O4B'—C14'—C15'—C17'13 (3)
C8B—C6B—N1B—N2B95.5 (2)O3B'—C14'—C15'—C17'167 (2)
C7B—C6B—N1B—N2B135.4 (2)O4B'—C14'—C15'—C16'139 (3)
S1B—C6B—N1B—N2B21.4 (2)O3B'—C14'—C15'—C16'41 (4)
O1A—C2A—N1A—N2A175.0 (2)O4B'—C14'—O3B'—C11B22 (3)
C1A—C2A—N1A—N2A5.1 (3)C15'—C14'—O3B'—C11B158.1 (18)
O1A—C2A—N1A—C6A5.0 (3)C12B—C11B—O3B'—C14'125.5 (14)
C1A—C2A—N1A—C6A175.1 (2)C10B—C11B—O3B'—C14'81.1 (17)
Hydrogen-bond geometry (Å, º) top
Cg2 and Cg4 are the centroids of the C8B–C13B and C8A–C13A rings, respectively.
D—H···AD—HH···AD···AD—H···A
O1—H1B···O4Bi0.88 (11)2.32 (10)3.111 (16)149 (12)
N3A—H3A···O1Bii0.861.992.842 (3)171
N3B—H3B···O1A0.861.942.792 (3)171
C15B—H15B···O10.982.463.368 (19)154
C7B—H7B2···O1iii0.962.493.434 (19)168
C15A—H15A···Cg2iv0.982.993.959 (4)168
C17B—H17B···Cg4iv0.962.983.864 (9)153
C17—H17H···Cg4iv0.962.933.81 (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.
4-(5-Acetamido-3-acetyl-2-methyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)phenyl propionate (III) top
Crystal data top
C16H19N3O4SZ = 4
Mr = 349.40F(000) = 736
Triclinic, P1Dx = 1.313 Mg m3
a = 11.4150 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.4021 (3) ÅCell parameters from 7257 reflections
c = 13.2305 (3) Åθ = 1.8–26.9°
α = 71.982 (1)°µ = 0.21 mm1
β = 89.829 (1)°T = 293 K
γ = 83.114 (1)°Block, colourless
V = 1767.18 (8) Å30.25 × 0.24 × 0.20 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer
5869 reflections with I > 2σ(I)
ω and φ scansRint = 0.022
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
θmax = 26.4°, θmin = 1.6°
Tmin = 0.756, Tmax = 0.824h = 1414
26933 measured reflectionsk = 1515
7257 independent reflectionsl = 1616
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-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 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.33 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
N1A0.57800 (12)1.34448 (11)0.74760 (12)0.0525 (3)
H1A0.6206811.3702760.7861450.063*
O1B0.30213 (13)0.50078 (14)0.84275 (14)0.0854 (5)
O2A0.73259 (12)0.86411 (11)0.91134 (11)0.0707 (4)
C5A0.51016 (19)1.54430 (15)0.65971 (18)0.0696 (5)
H5A10.5574771.5764330.6004180.104*
H5A20.5450551.5500890.7234590.104*
H5A30.4320111.5853000.6479050.104*
C5B0.41647 (18)0.3577 (2)0.9822 (2)0.0847 (7)
H5B10.4403460.2861500.9698050.127*
H5B20.4020350.3443921.0563660.127*
H5B30.4779120.4059290.9618670.127*
C4B0.30600 (16)0.41497 (16)0.91784 (16)0.0595 (4)
C4A0.50385 (16)1.42199 (14)0.67108 (15)0.0545 (4)
C3B0.09508 (14)0.40749 (12)0.90740 (12)0.0430 (3)
C3A0.58882 (13)1.22853 (13)0.76694 (12)0.0443 (3)
C2B0.20340 (15)0.38900 (14)0.93581 (13)0.0475 (4)
C2A0.74122 (16)0.96458 (16)0.90086 (14)0.0557 (4)
C1A0.8399 (2)1.0004 (2)0.95195 (19)0.0819 (7)
H1A10.8944610.9344230.9877540.123*
H1A20.8086221.0366051.0024610.123*
H1A30.8799631.0531370.8984540.123*
C1B0.20176 (18)0.30017 (18)1.04232 (15)0.0661 (5)
H1B10.2811710.2867951.0613710.099*
H1B20.1657560.3262301.0945010.099*
H1B30.1572970.2304411.0394800.099*
C6A0.56363 (14)1.02464 (13)0.77881 (13)0.0480 (4)
C6B0.08741 (14)0.49848 (13)0.78791 (12)0.0439 (3)
C7B0.15459 (18)0.61708 (14)0.77098 (15)0.0599 (5)
H7B10.2377760.6136730.7650990.090*
H7B20.1298310.6693630.7069020.090*
H7B30.1384290.6428050.8302980.090*
C7A0.46982 (17)0.97282 (17)0.85428 (16)0.0631 (5)
H7A10.4989290.8955500.8945760.095*
H7A20.3998010.9734110.8140050.095*
H7A30.4516001.0168240.9018430.095*
C8A0.60797 (14)0.95904 (13)0.70392 (13)0.0467 (4)
C8B0.11842 (13)0.44221 (13)0.70592 (12)0.0427 (3)
C13B0.11426 (16)0.32545 (14)0.73185 (13)0.0504 (4)
H13B0.0938420.2801520.8013090.060*
C9A0.53636 (16)0.89412 (15)0.66959 (16)0.0593 (4)
H9A0.4611510.8868910.6960480.071*
C12B0.13966 (17)0.27416 (15)0.65726 (14)0.0555 (4)
H12B0.1362800.1950770.6763410.067*
C10A0.57469 (17)0.83983 (15)0.59663 (16)0.0616 (5)
H10A0.5252980.7972370.5733550.074*
C11B0.16969 (15)0.33979 (16)0.55560 (14)0.0545 (4)
C11A0.68586 (16)0.84921 (13)0.55888 (14)0.0520 (4)
C10B0.1753 (2)0.45512 (18)0.52740 (16)0.0848 (7)
H10B0.1965070.4996650.4578710.102*
C12A0.75876 (17)0.91397 (17)0.59031 (16)0.0606 (4)
H12A0.8340580.9203410.5638620.073*
C13A0.71888 (16)0.96928 (16)0.66141 (15)0.0588 (4)
H13A0.7674101.0147390.6815960.071*
C9B0.1494 (2)0.50628 (16)0.60244 (15)0.0772 (7)
H9B0.1528760.5854100.5826060.093*
C14B0.11985 (18)0.23156 (17)0.43963 (15)0.0599 (4)
C14A0.75675 (15)0.84105 (14)0.39311 (14)0.0518 (4)
C15B0.1704 (2)0.18925 (18)0.35733 (16)0.0677 (5)
H15A0.2102890.2538230.3016500.081*
H15B0.2288480.1395180.3894710.081*
C15A0.81032 (18)0.75962 (16)0.33897 (16)0.0637 (5)
H15C0.7594330.7007280.3454610.076*
H15D0.8858160.7229480.3738240.076*
C16A0.8284 (2)0.8183 (2)0.22260 (18)0.0888 (7)
H16A0.7531540.8491160.1865840.133*
H16B0.8678500.7640590.1915670.133*
H16C0.8756230.8790790.2157320.133*
C16B0.0785 (2)0.1249 (2)0.30835 (19)0.0837 (7)
H16D0.0221360.1745210.2737530.126*
H16E0.1159930.0984690.2571530.126*
H16F0.0388250.0605810.3629600.126*
N1B0.20675 (12)0.36478 (12)0.95143 (11)0.0508 (3)
H1B0.2144850.3022211.0036640.061*
N2B0.00570 (12)0.36683 (11)0.95615 (10)0.0462 (3)
N2A0.66403 (12)1.16162 (11)0.83704 (11)0.0489 (3)
N3A0.66139 (12)1.04853 (11)0.83936 (11)0.0495 (3)
N3B0.09860 (11)0.42081 (11)0.89767 (10)0.0440 (3)
O1A0.43966 (13)1.39102 (11)0.61613 (12)0.0764 (4)
O2B0.29535 (10)0.43215 (11)0.88346 (10)0.0582 (3)
O3A0.72748 (12)0.78457 (10)0.49319 (10)0.0604 (3)
O3B0.20361 (12)0.29134 (13)0.47883 (11)0.0701 (4)
O4A0.73852 (12)0.94268 (10)0.35619 (10)0.0626 (3)
S1B0.07220 (4)0.51371 (4)0.78475 (3)0.05286 (12)
S1A0.50357 (4)1.16990 (4)0.69416 (4)0.05734 (14)
O4B0.0175 (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)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N1A0.0511 (8)0.0467 (7)0.0612 (8)0.0057 (6)0.0134 (7)0.0190 (6)
O1B0.0618 (9)0.0804 (10)0.0964 (11)0.0195 (7)0.0056 (8)0.0021 (9)
O2A0.0677 (8)0.0523 (7)0.0770 (9)0.0030 (6)0.0193 (7)0.0022 (6)
C5A0.0723 (13)0.0466 (10)0.0855 (14)0.0058 (9)0.0078 (11)0.0147 (9)
C5B0.0452 (11)0.0925 (16)0.1061 (18)0.0056 (10)0.0050 (11)0.0169 (14)
C4B0.0485 (10)0.0601 (11)0.0697 (12)0.0076 (8)0.0031 (9)0.0199 (9)
C4A0.0515 (10)0.0487 (9)0.0608 (10)0.0051 (7)0.0054 (8)0.0140 (8)
C3B0.0461 (9)0.0391 (7)0.0438 (8)0.0035 (6)0.0026 (7)0.0134 (6)
C3A0.0400 (8)0.0479 (8)0.0456 (8)0.0048 (6)0.0033 (7)0.0156 (7)
C2B0.0488 (9)0.0551 (9)0.0449 (8)0.0095 (7)0.0018 (7)0.0236 (7)
C2A0.0506 (10)0.0570 (10)0.0493 (9)0.0006 (8)0.0095 (8)0.0041 (8)
C1A0.0676 (13)0.0804 (14)0.0819 (14)0.0057 (11)0.0356 (11)0.0035 (11)
C1B0.0649 (12)0.0773 (13)0.0548 (10)0.0212 (10)0.0086 (9)0.0141 (9)
C6A0.0451 (9)0.0445 (8)0.0513 (9)0.0009 (7)0.0111 (7)0.0119 (7)
C6B0.0473 (9)0.0409 (8)0.0405 (8)0.0045 (6)0.0030 (7)0.0085 (6)
C7B0.0708 (12)0.0451 (9)0.0607 (11)0.0037 (8)0.0053 (9)0.0161 (8)
C7A0.0535 (10)0.0682 (11)0.0631 (11)0.0028 (9)0.0014 (9)0.0158 (9)
C8A0.0465 (9)0.0371 (7)0.0527 (9)0.0011 (6)0.0079 (7)0.0100 (7)
C8B0.0425 (8)0.0427 (8)0.0402 (8)0.0020 (6)0.0041 (6)0.0105 (6)
C13B0.0623 (10)0.0449 (8)0.0412 (8)0.0051 (7)0.0019 (7)0.0102 (7)
C9A0.0492 (10)0.0549 (10)0.0800 (13)0.0093 (8)0.0005 (9)0.0288 (9)
C12B0.0661 (11)0.0473 (9)0.0572 (10)0.0131 (8)0.0092 (8)0.0198 (8)
C10A0.0603 (11)0.0510 (10)0.0809 (13)0.0124 (8)0.0052 (10)0.0292 (9)
C11B0.0507 (9)0.0642 (10)0.0547 (10)0.0053 (8)0.0077 (8)0.0281 (8)
C11A0.0603 (10)0.0378 (8)0.0555 (9)0.0034 (7)0.0078 (8)0.0147 (7)
C10B0.137 (2)0.0612 (12)0.0497 (11)0.0032 (12)0.0350 (12)0.0127 (9)
C12A0.0523 (10)0.0676 (11)0.0669 (11)0.0107 (8)0.0035 (9)0.0269 (9)
C13A0.0569 (10)0.0612 (10)0.0673 (11)0.0190 (8)0.0005 (9)0.0286 (9)
C9B0.130 (2)0.0439 (9)0.0515 (10)0.0020 (11)0.0264 (11)0.0090 (8)
C14B0.0666 (12)0.0665 (11)0.0524 (10)0.0142 (10)0.0012 (9)0.0247 (9)
C14A0.0477 (9)0.0474 (9)0.0609 (10)0.0000 (7)0.0114 (8)0.0201 (8)
C15B0.0867 (14)0.0679 (12)0.0568 (11)0.0235 (10)0.0046 (10)0.0265 (9)
C15A0.0602 (11)0.0600 (11)0.0729 (12)0.0093 (9)0.0081 (9)0.0296 (9)
C16A0.0977 (18)0.0957 (17)0.0725 (14)0.0254 (14)0.0056 (12)0.0390 (13)
C16B0.1012 (18)0.0925 (16)0.0759 (14)0.0311 (14)0.0079 (13)0.0458 (13)
N1B0.0448 (7)0.0487 (7)0.0536 (8)0.0030 (6)0.0044 (6)0.0091 (6)
N2B0.0455 (7)0.0470 (7)0.0415 (7)0.0025 (6)0.0039 (6)0.0083 (6)
N2A0.0479 (8)0.0493 (7)0.0483 (7)0.0059 (6)0.0089 (6)0.0136 (6)
N3A0.0488 (8)0.0472 (7)0.0497 (7)0.0006 (6)0.0136 (6)0.0133 (6)
N3B0.0425 (7)0.0482 (7)0.0390 (6)0.0044 (5)0.0033 (5)0.0108 (5)
O1A0.0831 (10)0.0533 (7)0.0862 (10)0.0041 (7)0.0394 (8)0.0135 (7)
O2B0.0444 (6)0.0747 (8)0.0602 (7)0.0063 (6)0.0045 (6)0.0281 (6)
O3A0.0765 (8)0.0419 (6)0.0612 (7)0.0042 (6)0.0027 (6)0.0177 (5)
O3B0.0641 (8)0.0866 (9)0.0729 (9)0.0045 (7)0.0138 (7)0.0458 (8)
O4A0.0758 (9)0.0461 (7)0.0658 (8)0.0045 (6)0.0038 (6)0.0182 (6)
S1B0.0526 (2)0.0518 (2)0.0476 (2)0.01414 (18)0.00393 (18)0.00294 (18)
S1A0.0614 (3)0.0439 (2)0.0653 (3)0.00323 (18)0.0282 (2)0.01838 (19)
O4B0.0605 (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)
Geometric parameters (Å, º) top
N1A—C4A1.369 (2)C8A—C9A1.382 (2)
N1A—C3A1.371 (2)C8A—C13A1.388 (2)
N1A—H1A0.8600C8B—C9B1.376 (2)
O1B—C4B1.207 (2)C8B—C13B1.376 (2)
O2A—C2A1.226 (2)C13B—C12B1.377 (2)
C5A—C4A1.488 (2)C13B—H13B0.9300
C5A—H5A10.9600C9A—C10A1.380 (3)
C5A—H5A20.9600C9A—H9A0.9300
C5A—H5A30.9600C12B—C11B1.359 (2)
C5B—C4B1.496 (3)C12B—H12B0.9300
C5B—H5B10.9600C10A—C11A1.367 (3)
C5B—H5B20.9600C10A—H10A0.9300
C5B—H5B30.9600C11B—C10B1.355 (3)
C4B—N1B1.365 (2)C11B—O3B1.406 (2)
C4A—O1A1.207 (2)C11A—C12A1.371 (3)
C3B—N2B1.277 (2)C11A—O3A1.400 (2)
C3B—N1B1.377 (2)C10B—C9B1.383 (3)
C3B—S1B1.7420 (15)C10B—H10B0.9300
C3A—N2A1.2821 (19)C12A—C13A1.373 (3)
C3A—S1A1.7353 (16)C12A—H12A0.9300
C2B—O2B1.228 (2)C13A—H13A0.9300
C2B—N3B1.352 (2)C9B—H9B0.9300
C2B—C1B1.495 (2)C14B—O4B1.196 (7)
C2A—N3A1.352 (2)C14B—O4B'1.218 (14)
C2A—C1A1.494 (3)C14B—O3B1.341 (2)
C1A—H1A10.9600C14B—C15B1.491 (3)
C1A—H1A20.9600C14A—O4A1.195 (2)
C1A—H1A30.9600C14A—O3A1.355 (2)
C1B—H1B10.9600C14A—C15A1.484 (2)
C1B—H1B20.9600C15B—C16B1.508 (3)
C1B—H1B30.9600C15B—H15A0.9700
C6A—N3A1.485 (2)C15B—H15B0.9700
C6A—C8A1.515 (2)C15A—C16A1.511 (3)
C6A—C7A1.523 (3)C15A—H15C0.9700
C6A—S1A1.8520 (16)C15A—H15D0.9700
C6B—N3B1.4887 (19)C16A—H16A0.9600
C6B—C8B1.523 (2)C16A—H16B0.9600
C6B—C7B1.526 (2)C16A—H16C0.9600
C6B—S1B1.8531 (16)C16B—H16D0.9600
C7B—H7B10.9600C16B—H16E0.9600
C7B—H7B20.9600C16B—H16F0.9600
C7B—H7B30.9600N1B—H1B0.8600
C7A—H7A10.9600N2B—N3B1.3993 (17)
C7A—H7A20.9600N2A—N3A1.3973 (19)
C7A—H7A30.9600
C4A—N1A—C3A124.42 (14)C8B—C13B—H13B119.3
C4A—N1A—H1A117.8C12B—C13B—H13B119.3
C3A—N1A—H1A117.8C10A—C9A—C8A121.04 (17)
C4A—C5A—H5A1109.5C10A—C9A—H9A119.5
C4A—C5A—H5A2109.5C8A—C9A—H9A119.5
H5A1—C5A—H5A2109.5C11B—C12B—C13B119.62 (16)
C4A—C5A—H5A3109.5C11B—C12B—H12B120.2
H5A1—C5A—H5A3109.5C13B—C12B—H12B120.2
H5A2—C5A—H5A3109.5C11A—C10A—C9A119.44 (17)
C4B—C5B—H5B1109.5C11A—C10A—H10A120.3
C4B—C5B—H5B2109.5C9A—C10A—H10A120.3
H5B1—C5B—H5B2109.5C10B—C11B—C12B120.48 (16)
C4B—C5B—H5B3109.5C10B—C11B—O3B118.06 (16)
H5B1—C5B—H5B3109.5C12B—C11B—O3B121.31 (16)
H5B2—C5B—H5B3109.5C10A—C11A—C12A121.05 (17)
O1B—C4B—N1B121.23 (17)C10A—C11A—O3A118.62 (16)
O1B—C4B—C5B123.57 (18)C12A—C11A—O3A120.17 (17)
N1B—C4B—C5B115.18 (17)C11B—C10B—C9B119.73 (17)
O1A—C4A—N1A120.96 (16)C11B—C10B—H10B120.1
O1A—C4A—C5A123.29 (17)C9B—C10B—H10B120.1
N1A—C4A—C5A115.74 (16)C11A—C12A—C13A118.98 (18)
N2B—C3B—N1B119.51 (14)C11A—C12A—H12A120.5
N2B—C3B—S1B118.75 (12)C13A—C12A—H12A120.5
N1B—C3B—S1B121.73 (12)C12A—C13A—C8A121.63 (16)
N2A—C3A—N1A120.77 (14)C12A—C13A—H13A119.2
N2A—C3A—S1A118.74 (12)C8A—C13A—H13A119.2
N1A—C3A—S1A120.46 (11)C8B—C9B—C10B121.19 (17)
O2B—C2B—N3B120.27 (15)C8B—C9B—H9B119.4
O2B—C2B—C1B122.29 (16)C10B—C9B—H9B119.4
N3B—C2B—C1B117.44 (15)O4B—C14B—O3B120.9 (4)
O2A—C2A—N3A120.37 (16)O4B'—C14B—O3B121.3 (8)
O2A—C2A—C1A122.52 (16)O4B—C14B—C15B126.8 (4)
N3A—C2A—C1A117.10 (17)O4B'—C14B—C15B122.2 (11)
C2A—C1A—H1A1109.5O3B—C14B—C15B111.26 (17)
C2A—C1A—H1A2109.5O4A—C14A—O3A122.58 (16)
H1A1—C1A—H1A2109.5O4A—C14A—C15A126.69 (18)
C2A—C1A—H1A3109.5O3A—C14A—C15A110.72 (15)
H1A1—C1A—H1A3109.5C14B—C15B—C16B113.05 (19)
H1A2—C1A—H1A3109.5C14B—C15B—H15A109.0
C2B—C1B—H1B1109.5C16B—C15B—H15A109.0
C2B—C1B—H1B2109.5C14B—C15B—H15B109.0
H1B1—C1B—H1B2109.5C16B—C15B—H15B109.0
C2B—C1B—H1B3109.5H15A—C15B—H15B107.8
H1B1—C1B—H1B3109.5C14A—C15A—C16A111.95 (17)
H1B2—C1B—H1B3109.5C14A—C15A—H15C109.2
N3A—C6A—C8A112.33 (13)C16A—C15A—H15C109.2
N3A—C6A—C7A110.08 (14)C14A—C15A—H15D109.2
C8A—C6A—C7A115.48 (14)C16A—C15A—H15D109.2
N3A—C6A—S1A102.03 (10)H15C—C15A—H15D107.9
C8A—C6A—S1A106.50 (11)C15A—C16A—H16A109.5
C7A—C6A—S1A109.47 (12)C15A—C16A—H16B109.5
N3B—C6B—C8B110.60 (12)H16A—C16A—H16B109.5
N3B—C6B—C7B112.08 (13)C15A—C16A—H16C109.5
C8B—C6B—C7B114.21 (13)H16A—C16A—H16C109.5
N3B—C6B—S1B102.21 (10)H16B—C16A—H16C109.5
C8B—C6B—S1B109.71 (11)C15B—C16B—H16D109.5
C7B—C6B—S1B107.27 (12)C15B—C16B—H16E109.5
C6B—C7B—H7B1109.5H16D—C16B—H16E109.5
C6B—C7B—H7B2109.5C15B—C16B—H16F109.5
H7B1—C7B—H7B2109.5H16D—C16B—H16F109.5
C6B—C7B—H7B3109.5H16E—C16B—H16F109.5
H7B1—C7B—H7B3109.5C4B—N1B—C3B124.47 (15)
H7B2—C7B—H7B3109.5C4B—N1B—H1B117.8
C6A—C7A—H7A1109.5C3B—N1B—H1B117.8
C6A—C7A—H7A2109.5C3B—N2B—N3B110.39 (12)
H7A1—C7A—H7A2109.5C3A—N2A—N3A110.07 (13)
C6A—C7A—H7A3109.5C2A—N3A—N2A120.02 (14)
H7A1—C7A—H7A3109.5C2A—N3A—C6A122.34 (14)
H7A2—C7A—H7A3109.5N2A—N3A—C6A117.49 (12)
C9A—C8A—C13A117.81 (16)C2B—N3B—N2B119.44 (13)
C9A—C8A—C6A121.21 (15)C2B—N3B—C6B122.35 (13)
C13A—C8A—C6A120.81 (15)N2B—N3B—C6B117.53 (12)
C9B—C8B—C13B117.51 (15)C14A—O3A—C11A118.09 (13)
C9B—C8B—C6B121.12 (14)C14B—O3B—C11B118.32 (15)
C13B—C8B—C6B121.36 (13)C3B—S1B—C6B89.96 (7)
C8B—C13B—C12B121.48 (15)C3A—S1A—C6A89.90 (7)
C3A—N1A—C4A—O1A1.8 (3)S1B—C3B—N2B—N3B0.89 (18)
C3A—N1A—C4A—C5A177.04 (17)N1A—C3A—N2A—N3A177.85 (14)
C4A—N1A—C3A—N2A176.96 (17)S1A—C3A—N2A—N3A0.39 (19)
C4A—N1A—C3A—S1A1.2 (2)O2A—C2A—N3A—N2A172.94 (16)
N3A—C6A—C8A—C9A156.77 (15)C1A—C2A—N3A—N2A8.5 (3)
C7A—C6A—C8A—C9A29.4 (2)O2A—C2A—N3A—C6A2.5 (3)
S1A—C6A—C8A—C9A92.34 (16)C1A—C2A—N3A—C6A176.07 (18)
N3A—C6A—C8A—C13A28.1 (2)C3A—N2A—N3A—C2A173.99 (16)
C7A—C6A—C8A—C13A155.50 (16)C3A—N2A—N3A—C6A10.4 (2)
S1A—C6A—C8A—C13A82.75 (16)C8A—C6A—N3A—C2A56.7 (2)
N3B—C6B—C8B—C9B160.12 (18)C7A—C6A—N3A—C2A73.5 (2)
C7B—C6B—C8B—C9B32.6 (2)S1A—C6A—N3A—C2A170.36 (14)
S1B—C6B—C8B—C9B87.87 (19)C8A—C6A—N3A—N2A127.76 (14)
N3B—C6B—C8B—C13B21.2 (2)C7A—C6A—N3A—N2A102.04 (16)
C7B—C6B—C8B—C13B148.76 (16)S1A—C6A—N3A—N2A14.10 (17)
S1B—C6B—C8B—C13B90.79 (16)O2B—C2B—N3B—N2B176.98 (14)
C9B—C8B—C13B—C12B0.2 (3)C1B—C2B—N3B—N2B2.7 (2)
C6B—C8B—C13B—C12B178.50 (16)O2B—C2B—N3B—C6B6.7 (2)
C13A—C8A—C9A—C10A1.0 (3)C1B—C2B—N3B—C6B172.99 (15)
C6A—C8A—C9A—C10A176.22 (16)C3B—N2B—N3B—C2B179.54 (14)
C8B—C13B—C12B—C11B0.1 (3)C3B—N2B—N3B—C6B8.79 (19)
C8A—C9A—C10A—C11A0.9 (3)C8B—C6B—N3B—C2B65.22 (18)
C13B—C12B—C11B—C10B0.3 (3)C7B—C6B—N3B—C2B63.48 (19)
C13B—C12B—C11B—O3B175.85 (17)S1B—C6B—N3B—C2B178.04 (12)
C9A—C10A—C11A—C12A1.6 (3)C8B—C6B—N3B—N2B105.25 (15)
C9A—C10A—C11A—O3A173.75 (16)C7B—C6B—N3B—N2B126.05 (15)
C12B—C11B—C10B—C9B0.5 (4)S1B—C6B—N3B—N2B11.50 (15)
O3B—C11B—C10B—C9B176.2 (2)O4A—C14A—O3A—C11A6.9 (2)
C10A—C11A—C12A—C13A0.5 (3)C15A—C14A—O3A—C11A174.20 (15)
O3A—C11A—C12A—C13A174.87 (16)C10A—C11A—O3A—C14A119.16 (18)
C11A—C12A—C13A—C8A1.5 (3)C12A—C11A—O3A—C14A65.4 (2)
C9A—C8A—C13A—C12A2.2 (3)O4B—C14B—O3B—C11B9.4 (16)
C6A—C8A—C13A—C12A177.47 (16)O4B'—C14B—O3B—C11B27 (3)
C13B—C8B—C9B—C10B0.0 (3)C15B—C14B—O3B—C11B178.40 (16)
C6B—C8B—C9B—C10B178.7 (2)C10B—C11B—O3B—C14B110.6 (2)
C11B—C10B—C9B—C8B0.4 (4)C12B—C11B—O3B—C14B73.7 (2)
O4B—C14B—C15B—C16B9.9 (17)N2B—C3B—S1B—C6B5.09 (13)
O4B'—C14B—C15B—C16B27 (3)N1B—C3B—S1B—C6B173.34 (14)
O3B—C14B—C15B—C16B178.04 (18)N3B—C6B—S1B—C3B8.44 (10)
O4A—C14A—C15A—C16A6.8 (3)C8B—C6B—S1B—C3B108.95 (11)
O3A—C14A—C15A—C16A172.10 (18)C7B—C6B—S1B—C3B126.48 (12)
O1B—C4B—N1B—C3B2.5 (3)N2A—C3A—S1A—C6A6.85 (15)
C5B—C4B—N1B—C3B175.98 (18)N1A—C3A—S1A—C6A174.91 (14)
N2B—C3B—N1B—C4B167.01 (16)N3A—C6A—S1A—C3A10.64 (11)
S1B—C3B—N1B—C4B14.6 (2)C8A—C6A—S1A—C3A128.55 (11)
N1B—C3B—N2B—N3B179.36 (13)C7A—C6A—S1A—C3A105.95 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1A—H1A···O2Bi0.861.992.8469 (19)174
N1B—H1B···O2Aii0.862.042.860 (2)160
C9B—H9B···O3Aiii0.932.603.426 (2)148
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y+1, z+2; (iii) x1, y, z.
4-(5-Acetamido-3-acetyl-2-methyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)phenyl cinnamate chloroform hemisolvate (IV) top
Crystal data top
C22H21N3O4S·0.5CHCl3Z = 4
Mr = 483.16F(000) = 1004
Triclinic, P1Dx = 1.350 Mg m3
a = 10.7427 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.0828 (2) ÅCell parameters from 8335 reflections
c = 20.8969 (3) Åθ = 1.8–26.9°
α = 93.186 (1)°µ = 0.34 mm1
β = 103.945 (4)°T = 293 K
γ = 98.489 (2)°Block, colourless
V = 2377.39 (7) Å30.30 × 0.25 × 0.20 mm
Data collection top
Bruker Kappa APEXII CCD
diffractometer
6495 reflections with I > 2σ(I)
ω and φ scansRint = 0.027
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
θmax = 25.0°, θmin = 1.9°
Tmin = 0.741, Tmax = 0.856h = 1212
31719 measured reflectionsk = 1313
8335 independent reflectionsl = 2424
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.058Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.195H-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 parametersΔρmax = 0.54 e Å3
0 restraintsΔρmin = 0.60 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C1A0.7194 (4)0.1544 (3)0.06419 (17)0.0762 (10)
H1A10.6794160.2059160.0327120.114*
H1A20.6569470.1173240.0862770.114*
H1A30.7499890.0915550.0415800.114*
C1B0.6139 (3)0.7996 (3)0.05275 (15)0.0639 (8)
H1B10.6954800.8545370.0644420.096*
H1B20.5443210.8454800.0515550.096*
H1B30.6025890.7570190.0099510.096*
C2A0.8309 (3)0.2293 (3)0.11376 (14)0.0533 (7)
C2B0.6126 (3)0.7094 (2)0.10287 (13)0.0484 (6)
C3A0.9511 (2)0.0017 (2)0.20325 (12)0.0428 (5)
C3B0.3223 (2)0.5173 (2)0.03235 (12)0.0427 (5)
C4A1.0210 (3)0.1768 (3)0.25439 (14)0.0513 (6)
C4B0.1169 (3)0.3955 (3)0.02802 (15)0.0583 (7)
C5A0.9753 (3)0.3054 (3)0.26544 (17)0.0680 (8)
H5A11.0456850.3511010.2696220.102*
H5A20.9051210.3419040.2285570.102*
H5A30.9457100.3062280.3052630.102*
C5B0.0036 (3)0.3916 (4)0.08641 (18)0.0799 (10)
H5B10.0515810.3132630.0922020.120*
H5B20.0344380.4039200.1254140.120*
H5B30.0446940.4550460.0791130.120*
C6A1.0106 (2)0.2332 (2)0.21533 (13)0.0465 (6)
C6B0.4970 (2)0.5235 (2)0.13959 (12)0.0432 (5)
C7A1.1137 (3)0.3185 (3)0.19223 (17)0.0632 (8)
H7A11.1288090.2802810.1530570.095*
H7A21.1932020.3340940.2265580.095*
H7A31.0835620.3944380.1826040.095*
C7B0.6069 (3)0.4474 (3)0.14865 (15)0.0574 (7)
H7B10.6115520.4137040.1061320.086*
H7B20.5901350.3821200.1753040.086*
H7B30.6879980.4988270.1701960.086*
C8A0.9573 (2)0.2918 (2)0.26755 (13)0.0439 (6)
C8B0.4791 (2)0.5838 (2)0.20332 (12)0.0430 (5)
C9A0.8302 (3)0.2560 (3)0.27116 (15)0.0579 (7)
H9A0.7749200.1973010.2393390.069*
C9B0.5678 (3)0.5896 (3)0.26339 (14)0.0604 (7)
H9B0.6423410.5548290.2660190.072*
C10A0.7844 (3)0.3056 (3)0.32095 (16)0.0636 (8)
H10A0.6988350.2806330.3226810.076*
C10B0.5487 (3)0.6453 (3)0.31927 (15)0.0672 (8)
H10B0.6091210.6468860.3596780.081*
C11A0.8654 (3)0.3919 (3)0.36804 (14)0.0549 (7)
C11B0.4411 (3)0.6985 (3)0.31586 (14)0.0543 (7)
C12A0.9920 (3)0.4299 (3)0.36570 (15)0.0574 (7)
H12A1.0466850.4886700.3976630.069*
C12B0.3529 (3)0.6951 (4)0.25795 (16)0.0733 (9)
H12B0.2795420.7315600.2557710.088*
C13A1.0363 (3)0.3802 (3)0.31574 (14)0.0530 (7)
H13A1.1217320.4063250.3140390.064*
C13B0.3712 (3)0.6372 (4)0.20168 (15)0.0702 (9)
H13B0.3091140.6343590.1617430.084*
C14A0.8162 (3)0.5525 (3)0.43336 (15)0.0570 (7)
C14B0.3303 (3)0.7229 (3)0.39933 (14)0.0551 (7)
C15A0.7524 (3)0.5734 (3)0.48581 (14)0.0606 (7)
H15A0.7227880.5074540.5069140.073*
C15B0.3246 (3)0.8066 (3)0.45431 (14)0.0590 (7)
H15B0.3958470.8671810.4730690.071*
C16A0.7357 (3)0.6851 (3)0.50409 (14)0.0582 (7)
H16A0.7671230.7476090.4813410.070*
C16B0.2218 (3)0.7990 (3)0.47811 (14)0.0563 (7)
H16B0.1541120.7353130.4588270.068*
C17A0.6744 (3)0.7222 (3)0.55536 (14)0.0571 (7)
C17B0.2007 (3)0.8783 (3)0.53116 (13)0.0527 (6)
C18A0.6129 (4)0.6396 (3)0.5895 (2)0.0805 (10)
H18A0.6078880.5560280.5792600.097*
C18B0.0791 (3)0.8648 (4)0.54331 (18)0.0796 (10)
H18B0.0123760.8056200.5178420.096*
C19A0.5588 (4)0.6798 (4)0.6385 (2)0.0973 (13)
H19A0.5166470.6230960.6606920.117*
C19B0.0559 (4)0.9382 (5)0.5928 (2)0.1002 (14)
H19B0.0262870.9278280.6008610.120*
C20A0.5667 (4)0.8028 (4)0.6549 (2)0.0883 (12)
H20A0.5300130.8294400.6879960.106*
C20B0.1510 (5)1.0252 (4)0.6299 (2)0.0951 (13)
H20B0.1336991.0757340.6625920.114*
C21A0.6284 (3)0.8853 (4)0.62237 (18)0.0754 (10)
H21A0.6347200.9687810.6336530.090*
C21B0.2717 (5)1.0388 (4)0.61940 (19)0.0928 (13)
H21B0.3376691.0980620.6453710.111*
C22A0.6817 (3)0.8462 (3)0.57277 (16)0.0656 (8)
H22A0.7231420.9036870.5506830.079*
C22B0.2968 (3)0.9659 (3)0.57086 (16)0.0704 (9)
H22B0.3802550.9754830.5644330.085*
C241.3645 (7)0.9979 (5)0.1756 (3)0.1254 (18)
H241.3202000.9998960.2113980.150*
N1A0.9043 (2)0.1694 (2)0.15926 (10)0.0479 (5)
N1B0.5106 (2)0.61660 (19)0.09130 (10)0.0433 (5)
N2A0.9315 (2)0.1208 (2)0.21358 (11)0.0470 (5)
H2A0.8584130.1647520.1930760.056*
N2B0.2116 (2)0.4957 (2)0.01916 (11)0.0502 (5)
H2B0.2016570.5489810.0475550.060*
N3A0.8666 (2)0.04364 (19)0.16030 (11)0.0469 (5)
N3B0.4087 (2)0.61029 (19)0.03472 (10)0.0445 (5)
O1A0.8567 (2)0.34125 (19)0.11497 (11)0.0623 (5)
O1B0.70071 (19)0.7159 (2)0.15333 (10)0.0637 (5)
O2A1.1291 (2)0.1226 (2)0.28060 (13)0.0768 (7)
O2B0.1249 (3)0.3165 (2)0.00948 (13)0.0913 (8)
O3A0.8151 (2)0.4318 (2)0.42002 (11)0.0691 (6)
O3B0.4300 (2)0.7646 (2)0.37297 (10)0.0688 (6)
O4A0.8612 (3)0.6288 (2)0.40394 (13)0.0848 (8)
O4B0.2575 (2)0.6284 (2)0.37835 (12)0.0732 (6)
Cl11.5222 (2)0.9672 (2)0.20900 (13)0.1808 (8)
Cl21.2776 (3)0.8889 (2)0.11689 (11)0.2206 (13)
Cl31.3765 (3)1.14052 (19)0.14707 (17)0.2181 (12)
S1A1.08765 (6)0.10243 (6)0.24908 (4)0.0508 (2)
S1B0.34553 (7)0.42085 (6)0.09567 (3)0.0545 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.082 (2)0.065 (2)0.067 (2)0.0200 (17)0.0145 (17)0.0092 (16)
C1B0.0673 (18)0.0550 (17)0.0610 (17)0.0091 (14)0.0098 (14)0.0149 (14)
C2A0.0551 (15)0.0531 (17)0.0535 (15)0.0188 (13)0.0101 (13)0.0093 (12)
C2B0.0463 (14)0.0460 (14)0.0510 (15)0.0035 (11)0.0110 (12)0.0059 (11)
C3A0.0395 (12)0.0463 (14)0.0437 (13)0.0122 (10)0.0097 (10)0.0046 (11)
C3B0.0470 (13)0.0409 (13)0.0413 (13)0.0067 (11)0.0136 (10)0.0038 (10)
C4A0.0485 (15)0.0518 (15)0.0544 (15)0.0179 (12)0.0084 (12)0.0055 (12)
C4B0.0587 (16)0.0536 (17)0.0563 (16)0.0040 (13)0.0114 (13)0.0007 (14)
C5A0.0688 (19)0.0624 (19)0.071 (2)0.0157 (15)0.0074 (16)0.0210 (15)
C5B0.068 (2)0.076 (2)0.075 (2)0.0125 (17)0.0051 (17)0.0012 (18)
C6A0.0375 (12)0.0462 (14)0.0553 (15)0.0080 (10)0.0090 (11)0.0094 (11)
C6B0.0468 (13)0.0433 (13)0.0422 (13)0.0083 (10)0.0143 (10)0.0106 (10)
C7A0.0517 (16)0.0670 (19)0.0725 (19)0.0017 (14)0.0215 (14)0.0158 (15)
C7B0.0640 (17)0.0566 (17)0.0588 (16)0.0224 (14)0.0210 (14)0.0104 (13)
C8A0.0391 (12)0.0391 (13)0.0522 (14)0.0072 (10)0.0072 (11)0.0106 (11)
C8B0.0404 (12)0.0481 (14)0.0416 (13)0.0088 (10)0.0104 (10)0.0097 (10)
C9A0.0432 (14)0.0574 (17)0.0686 (18)0.0024 (12)0.0151 (13)0.0080 (14)
C9B0.0535 (16)0.079 (2)0.0504 (16)0.0248 (14)0.0077 (13)0.0047 (14)
C10A0.0484 (15)0.0632 (19)0.080 (2)0.0017 (13)0.0239 (15)0.0034 (16)
C10B0.0640 (18)0.089 (2)0.0446 (15)0.0199 (16)0.0038 (13)0.0036 (15)
C11A0.0644 (17)0.0493 (15)0.0547 (16)0.0140 (13)0.0188 (13)0.0063 (12)
C11B0.0523 (15)0.0601 (17)0.0498 (15)0.0003 (13)0.0195 (12)0.0050 (13)
C12A0.0552 (16)0.0505 (16)0.0596 (17)0.0053 (13)0.0051 (13)0.0037 (13)
C12B0.0629 (18)0.103 (3)0.0615 (18)0.0410 (18)0.0159 (15)0.0015 (18)
C13A0.0397 (13)0.0475 (15)0.0659 (17)0.0024 (11)0.0054 (12)0.0017 (13)
C13B0.0597 (18)0.106 (3)0.0482 (16)0.0386 (18)0.0066 (14)0.0016 (16)
C14A0.0629 (17)0.0595 (18)0.0515 (15)0.0194 (14)0.0134 (13)0.0090 (14)
C14B0.0583 (16)0.0581 (17)0.0510 (15)0.0077 (14)0.0195 (13)0.0038 (13)
C15A0.0626 (17)0.070 (2)0.0518 (16)0.0162 (15)0.0148 (14)0.0086 (14)
C15B0.0604 (17)0.0621 (18)0.0525 (16)0.0006 (14)0.0185 (13)0.0034 (13)
C16A0.0579 (16)0.0639 (18)0.0537 (16)0.0156 (14)0.0118 (13)0.0082 (13)
C16B0.0610 (17)0.0563 (17)0.0521 (15)0.0044 (13)0.0188 (13)0.0036 (13)
C17A0.0501 (15)0.0641 (18)0.0551 (16)0.0129 (13)0.0084 (12)0.0005 (14)
C17B0.0589 (16)0.0563 (16)0.0472 (14)0.0114 (13)0.0196 (12)0.0082 (12)
C18A0.087 (2)0.065 (2)0.100 (3)0.0131 (18)0.046 (2)0.0006 (19)
C18B0.0610 (19)0.103 (3)0.076 (2)0.0076 (18)0.0262 (17)0.005 (2)
C19A0.104 (3)0.091 (3)0.115 (3)0.009 (2)0.066 (3)0.008 (2)
C19B0.079 (3)0.144 (4)0.093 (3)0.034 (3)0.046 (2)0.001 (3)
C20A0.078 (2)0.098 (3)0.093 (3)0.008 (2)0.038 (2)0.020 (2)
C20B0.126 (4)0.099 (3)0.074 (2)0.031 (3)0.047 (3)0.009 (2)
C21A0.0651 (19)0.074 (2)0.080 (2)0.0074 (17)0.0121 (17)0.0206 (18)
C21B0.116 (3)0.087 (3)0.069 (2)0.013 (2)0.035 (2)0.017 (2)
C22A0.0594 (17)0.069 (2)0.0665 (19)0.0123 (15)0.0124 (15)0.0028 (15)
C22B0.0693 (19)0.078 (2)0.0634 (19)0.0020 (16)0.0272 (16)0.0027 (16)
C240.168 (5)0.093 (3)0.119 (4)0.023 (3)0.043 (4)0.006 (3)
N1A0.0458 (11)0.0486 (12)0.0466 (12)0.0108 (9)0.0037 (9)0.0088 (9)
N1B0.0444 (11)0.0436 (11)0.0404 (11)0.0034 (9)0.0091 (9)0.0086 (9)
N2A0.0415 (11)0.0471 (12)0.0500 (12)0.0090 (9)0.0055 (9)0.0059 (9)
N2B0.0505 (12)0.0498 (13)0.0457 (12)0.0005 (10)0.0067 (10)0.0097 (10)
N3A0.0456 (11)0.0440 (12)0.0479 (12)0.0093 (9)0.0045 (9)0.0055 (9)
N3B0.0440 (11)0.0464 (12)0.0399 (11)0.0032 (9)0.0065 (9)0.0059 (9)
O1A0.0632 (12)0.0530 (12)0.0688 (13)0.0158 (9)0.0061 (10)0.0190 (10)
O1B0.0515 (11)0.0662 (13)0.0604 (12)0.0058 (9)0.0027 (9)0.0112 (10)
O2A0.0540 (12)0.0581 (13)0.1058 (18)0.0173 (10)0.0092 (12)0.0100 (12)
O2B0.0909 (18)0.0728 (16)0.0852 (17)0.0283 (13)0.0044 (14)0.0229 (14)
O3A0.0904 (16)0.0576 (13)0.0693 (13)0.0136 (11)0.0388 (12)0.0051 (10)
O3B0.0651 (12)0.0771 (15)0.0625 (12)0.0080 (11)0.0302 (10)0.0173 (11)
O4A0.121 (2)0.0660 (15)0.0900 (17)0.0323 (14)0.0583 (16)0.0181 (13)
O4B0.0861 (15)0.0571 (13)0.0781 (15)0.0089 (12)0.0397 (12)0.0078 (11)
Cl10.1491 (16)0.1571 (16)0.220 (2)0.0242 (13)0.0127 (15)0.0345 (15)
Cl20.292 (3)0.1581 (18)0.1448 (16)0.0026 (19)0.0530 (18)0.0216 (13)
Cl30.261 (3)0.1176 (13)0.342 (3)0.0661 (16)0.164 (3)0.1005 (18)
S1A0.0372 (3)0.0504 (4)0.0610 (4)0.0115 (3)0.0027 (3)0.0053 (3)
S1B0.0620 (4)0.0483 (4)0.0473 (4)0.0053 (3)0.0097 (3)0.0128 (3)
Geometric parameters (Å, º) top
C1A—C2A1.487 (4)C10B—H10B0.9300
C1A—H1A10.9600C11A—C12A1.376 (4)
C1A—H1A20.9600C11A—O3A1.403 (3)
C1A—H1A30.9600C11B—C12B1.340 (4)
C1B—C2B1.489 (4)C11B—O3B1.404 (3)
C1B—H1B10.9600C12A—C13A1.369 (4)
C1B—H1B20.9600C12A—H12A0.9300
C1B—H1B30.9600C12B—C13B1.377 (4)
C2A—O1A1.228 (3)C12B—H12B0.9300
C2A—N1A1.353 (3)C13A—H13A0.9300
C2B—O1B1.226 (3)C13B—H13B0.9300
C2B—N1B1.352 (3)C14A—O4A1.187 (4)
C3A—N3A1.275 (3)C14A—O3A1.350 (4)
C3A—N2A1.379 (3)C14A—C15A1.451 (4)
C3A—S1A1.742 (3)C14B—O4B1.202 (4)
C3B—N3B1.271 (3)C14B—O3B1.353 (4)
C3B—N2B1.379 (3)C14B—C15B1.455 (4)
C3B—S1B1.741 (3)C15A—C16A1.325 (4)
C4A—O2A1.209 (3)C15A—H15A0.9300
C4A—N2A1.370 (3)C15B—C16B1.310 (4)
C4A—C5A1.486 (4)C15B—H15B0.9300
C4B—O2B1.206 (4)C16A—C17A1.457 (4)
C4B—N2B1.362 (4)C16A—H16A0.9300
C4B—C5B1.495 (4)C16B—C17B1.457 (4)
C5A—H5A10.9600C16B—H16B0.9300
C5A—H5A20.9600C17A—C18A1.379 (5)
C5A—H5A30.9600C17A—C22A1.388 (4)
C5B—H5B10.9600C17B—C22B1.378 (4)
C5B—H5B20.9600C17B—C18B1.379 (4)
C5B—H5B30.9600C18A—C19A1.378 (5)
C6A—N1A1.484 (3)C18A—H18A0.9300
C6A—C8A1.508 (4)C18B—C19B1.373 (5)
C6A—C7A1.533 (4)C18B—H18B0.9300
C6A—S1A1.863 (3)C19A—C20A1.372 (6)
C6B—N1B1.499 (3)C19A—H19A0.9300
C6B—C8B1.523 (3)C19B—C20B1.348 (7)
C6B—C7B1.531 (4)C19B—H19B0.9300
C6B—S1B1.845 (3)C20A—C21A1.358 (6)
C7A—H7A10.9600C20A—H20A0.9300
C7A—H7A20.9600C20B—C21B1.355 (6)
C7A—H7A30.9600C20B—H20B0.9300
C7B—H7B10.9600C21A—C22A1.378 (5)
C7B—H7B20.9600C21A—H21A0.9300
C7B—H7B30.9600C21B—C22B1.364 (5)
C8A—C9A1.386 (4)C21B—H21B0.9300
C8A—C13A1.388 (4)C22A—H22A0.9300
C8B—C13B1.371 (4)C22B—H22B0.9300
C8B—C9B1.373 (4)C24—Cl21.669 (6)
C9A—C10A1.375 (4)C24—Cl31.718 (6)
C9A—H9A0.9300C24—Cl11.761 (7)
C9B—C10B1.363 (4)C24—H240.9800
C9B—H9B0.9300N1A—N3A1.396 (3)
C10A—C11A1.370 (4)N1B—N3B1.395 (3)
C10A—H10A0.9300N2A—H2A0.8600
C10B—C11B1.362 (4)N2B—H2B0.8600
C2A—C1A—H1A1109.5C13A—C12A—C11A119.2 (3)
C2A—C1A—H1A2109.5C13A—C12A—H12A120.4
H1A1—C1A—H1A2109.5C11A—C12A—H12A120.4
C2A—C1A—H1A3109.5C11B—C12B—C13B119.7 (3)
H1A1—C1A—H1A3109.5C11B—C12B—H12B120.1
H1A2—C1A—H1A3109.5C13B—C12B—H12B120.1
C2B—C1B—H1B1109.5C12A—C13A—C8A121.8 (3)
C2B—C1B—H1B2109.5C12A—C13A—H13A119.1
H1B1—C1B—H1B2109.5C8A—C13A—H13A119.1
C2B—C1B—H1B3109.5C8B—C13B—C12B121.4 (3)
H1B1—C1B—H1B3109.5C8B—C13B—H13B119.3
H1B2—C1B—H1B3109.5C12B—C13B—H13B119.3
O1A—C2A—N1A120.1 (3)O4A—C14A—O3A122.9 (3)
O1A—C2A—C1A122.7 (2)O4A—C14A—C15A126.1 (3)
N1A—C2A—C1A117.2 (3)O3A—C14A—C15A111.0 (3)
O1B—C2B—N1B119.5 (2)O4B—C14B—O3B122.5 (3)
O1B—C2B—C1B122.4 (2)O4B—C14B—C15B126.1 (3)
N1B—C2B—C1B118.1 (2)O3B—C14B—C15B111.4 (3)
N3A—C3A—N2A119.8 (2)C16A—C15A—C14A121.0 (3)
N3A—C3A—S1A118.7 (2)C16A—C15A—H15A119.5
N2A—C3A—S1A121.56 (18)C14A—C15A—H15A119.5
N3B—C3B—N2B119.9 (2)C16B—C15B—C14B121.8 (3)
N3B—C3B—S1B118.86 (19)C16B—C15B—H15B119.1
N2B—C3B—S1B121.26 (19)C14B—C15B—H15B119.1
O2A—C4A—N2A121.2 (3)C15A—C16A—C17A128.1 (3)
O2A—C4A—C5A122.9 (3)C15A—C16A—H16A115.9
N2A—C4A—C5A115.9 (2)C17A—C16A—H16A115.9
O2B—C4B—N2B121.5 (3)C15B—C16B—C17B127.8 (3)
O2B—C4B—C5B123.0 (3)C15B—C16B—H16B116.1
N2B—C4B—C5B115.5 (3)C17B—C16B—H16B116.1
C4A—C5A—H5A1109.5C18A—C17A—C22A118.0 (3)
C4A—C5A—H5A2109.5C18A—C17A—C16A123.0 (3)
H5A1—C5A—H5A2109.5C22A—C17A—C16A119.0 (3)
C4A—C5A—H5A3109.5C22B—C17B—C18B117.7 (3)
H5A1—C5A—H5A3109.5C22B—C17B—C16B123.5 (3)
H5A2—C5A—H5A3109.5C18B—C17B—C16B118.9 (3)
C4B—C5B—H5B1109.5C19A—C18A—C17A120.6 (4)
C4B—C5B—H5B2109.5C19A—C18A—H18A119.7
H5B1—C5B—H5B2109.5C17A—C18A—H18A119.7
C4B—C5B—H5B3109.5C19B—C18B—C17B120.3 (4)
H5B1—C5B—H5B3109.5C19B—C18B—H18B119.8
H5B2—C5B—H5B3109.5C17B—C18B—H18B119.8
N1A—C6A—C8A111.2 (2)C20A—C19A—C18A120.5 (4)
N1A—C6A—C7A112.5 (2)C20A—C19A—H19A119.7
C8A—C6A—C7A114.9 (2)C18A—C19A—H19A119.7
N1A—C6A—S1A101.33 (16)C20B—C19B—C18B120.7 (4)
C8A—C6A—S1A108.81 (17)C20B—C19B—H19B119.6
C7A—C6A—S1A107.09 (18)C18B—C19B—H19B119.6
N1B—C6B—C8B110.5 (2)C21A—C20A—C19A119.6 (4)
N1B—C6B—C7B111.1 (2)C21A—C20A—H20A120.2
C8B—C6B—C7B115.2 (2)C19A—C20A—H20A120.2
N1B—C6B—S1B102.28 (15)C19B—C20B—C21B119.9 (4)
C8B—C6B—S1B109.63 (16)C19B—C20B—H20B120.1
C7B—C6B—S1B107.21 (19)C21B—C20B—H20B120.1
C6A—C7A—H7A1109.5C20A—C21A—C22A120.4 (3)
C6A—C7A—H7A2109.5C20A—C21A—H21A119.8
H7A1—C7A—H7A2109.5C22A—C21A—H21A119.8
C6A—C7A—H7A3109.5C20B—C21B—C22B120.1 (4)
H7A1—C7A—H7A3109.5C20B—C21B—H21B119.9
H7A2—C7A—H7A3109.5C22B—C21B—H21B119.9
C6B—C7B—H7B1109.5C21A—C22A—C17A120.9 (3)
C6B—C7B—H7B2109.5C21A—C22A—H22A119.6
H7B1—C7B—H7B2109.5C17A—C22A—H22A119.6
C6B—C7B—H7B3109.5C21B—C22B—C17B121.2 (3)
H7B1—C7B—H7B3109.5C21B—C22B—H22B119.4
H7B2—C7B—H7B3109.5C17B—C22B—H22B119.4
C9A—C8A—C13A117.6 (3)Cl2—C24—Cl3112.3 (4)
C9A—C8A—C6A121.6 (2)Cl2—C24—Cl1111.7 (3)
C13A—C8A—C6A120.7 (2)Cl3—C24—Cl1108.8 (4)
C13B—C8B—C9B117.3 (2)Cl2—C24—H24107.9
C13B—C8B—C6B119.6 (2)Cl3—C24—H24107.9
C9B—C8B—C6B123.0 (2)Cl1—C24—H24107.9
C10A—C9A—C8A121.1 (3)C2A—N1A—N3A118.9 (2)
C10A—C9A—H9A119.4C2A—N1A—C6A123.1 (2)
C8A—C9A—H9A119.4N3A—N1A—C6A117.22 (19)
C10B—C9B—C8B121.3 (3)C2B—N1B—N3B119.7 (2)
C10B—C9B—H9B119.4C2B—N1B—C6B122.5 (2)
C8B—C9B—H9B119.4N3B—N1B—C6B117.59 (19)
C11A—C10A—C9A119.7 (3)C4A—N2A—C3A124.2 (2)
C11A—C10A—H10A120.1C4A—N2A—H2A117.9
C9A—C10A—H10A120.1C3A—N2A—H2A117.9
C11B—C10B—C9B119.9 (3)C4B—N2B—C3B124.3 (2)
C11B—C10B—H10B120.0C4B—N2B—H2B117.8
C9B—C10B—H10B120.0C3B—N2B—H2B117.8
C10A—C11A—C12A120.6 (3)C3A—N3A—N1A110.1 (2)
C10A—C11A—O3A116.6 (3)C3B—N3B—N1B110.6 (2)
C12A—C11A—O3A122.7 (3)C14A—O3A—C11A119.8 (2)
C12B—C11B—C10B120.3 (3)C14B—O3B—C11B117.8 (2)
C12B—C11B—O3B120.9 (3)C3A—S1A—C6A89.27 (11)
C10B—C11B—O3B118.6 (3)C3B—S1B—C6B90.27 (11)
N1A—C6A—C8A—C9A18.9 (3)C18B—C17B—C22B—C21B1.6 (5)
C7A—C6A—C8A—C9A148.1 (3)C16B—C17B—C22B—C21B179.2 (3)
S1A—C6A—C8A—C9A91.9 (3)O1A—C2A—N1A—N3A174.7 (2)
N1A—C6A—C8A—C13A164.1 (2)C1A—C2A—N1A—N3A4.5 (4)
C7A—C6A—C8A—C13A34.9 (3)O1A—C2A—N1A—C6A5.1 (4)
S1A—C6A—C8A—C13A85.1 (3)C1A—C2A—N1A—C6A174.1 (3)
N1B—C6B—C8B—C13B63.4 (3)C8A—C6A—N1A—C2A73.6 (3)
C7B—C6B—C8B—C13B169.6 (3)C7A—C6A—N1A—C2A56.8 (3)
S1B—C6B—C8B—C13B48.6 (3)S1A—C6A—N1A—C2A170.9 (2)
N1B—C6B—C8B—C9B115.5 (3)C8A—C6A—N1A—N3A96.1 (2)
C7B—C6B—C8B—C9B11.5 (4)C7A—C6A—N1A—N3A133.4 (2)
S1B—C6B—C8B—C9B132.5 (3)S1A—C6A—N1A—N3A19.4 (2)
C13A—C8A—C9A—C10A0.4 (4)O1B—C2B—N1B—N3B178.5 (2)
C6A—C8A—C9A—C10A176.7 (3)C1B—C2B—N1B—N3B2.1 (4)
C13B—C8B—C9B—C10B0.6 (5)O1B—C2B—N1B—C6B3.1 (4)
C6B—C8B—C9B—C10B179.5 (3)C1B—C2B—N1B—C6B177.6 (2)
C8A—C9A—C10A—C11A0.1 (5)C8B—C6B—N1B—C2B65.2 (3)
C8B—C9B—C10B—C11B1.2 (5)C7B—C6B—N1B—C2B64.0 (3)
C9A—C10A—C11A—C12A0.4 (5)S1B—C6B—N1B—C2B178.2 (2)
C9A—C10A—C11A—O3A175.4 (3)C8B—C6B—N1B—N3B110.4 (2)
C9B—C10B—C11B—C12B0.9 (5)C7B—C6B—N1B—N3B120.4 (2)
C9B—C10B—C11B—O3B174.3 (3)S1B—C6B—N1B—N3B6.3 (2)
C10A—C11A—C12A—C13A0.1 (5)O2A—C4A—N2A—C3A5.8 (4)
O3A—C11A—C12A—C13A175.4 (3)C5A—C4A—N2A—C3A172.6 (3)
C10B—C11B—C12B—C13B0.1 (6)N3A—C3A—N2A—C4A174.3 (2)
O3B—C11B—C12B—C13B175.2 (3)S1A—C3A—N2A—C4A7.2 (4)
C11A—C12A—C13A—C8A0.4 (4)O2B—C4B—N2B—C3B0.7 (5)
C9A—C8A—C13A—C12A0.7 (4)C5B—C4B—N2B—C3B178.8 (3)
C6A—C8A—C13A—C12A176.5 (3)N3B—C3B—N2B—C4B176.4 (3)
C9B—C8B—C13B—C12B0.4 (5)S1B—C3B—N2B—C4B4.9 (4)
C6B—C8B—C13B—C12B178.5 (3)N2A—C3A—N3A—N1A178.5 (2)
C11B—C12B—C13B—C8B0.7 (6)S1A—C3A—N3A—N1A0.0 (3)
O4A—C14A—C15A—C16A2.2 (5)C2A—N1A—N3A—C3A175.8 (2)
O3A—C14A—C15A—C16A176.0 (3)C6A—N1A—N3A—C3A14.0 (3)
O4B—C14B—C15B—C16B14.4 (5)N2B—C3B—N3B—N1B178.6 (2)
O3B—C14B—C15B—C16B165.3 (3)S1B—C3B—N3B—N1B0.2 (3)
C14A—C15A—C16A—C17A180.0 (3)C2B—N1B—N3B—C3B179.9 (2)
C14B—C15B—C16B—C17B177.9 (3)C6B—N1B—N3B—C3B4.4 (3)
C15A—C16A—C17A—C18A5.9 (5)O4A—C14A—O3A—C11A2.0 (5)
C15A—C16A—C17A—C22A171.7 (3)C15A—C14A—O3A—C11A176.3 (2)
C15B—C16B—C17B—C22B9.2 (5)C10A—C11A—O3A—C14A125.4 (3)
C15B—C16B—C17B—C18B171.7 (3)C12A—C11A—O3A—C14A58.9 (4)
C22A—C17A—C18A—C19A1.0 (6)O4B—C14B—O3B—C11B5.0 (5)
C16A—C17A—C18A—C19A178.6 (4)C15B—C14B—O3B—C11B174.7 (3)
C22B—C17B—C18B—C19B0.9 (6)C12B—C11B—O3B—C14B68.0 (4)
C16B—C17B—C18B—C19B179.8 (4)C10B—C11B—O3B—C14B116.7 (3)
C17A—C18A—C19A—C20A0.9 (7)N3A—C3A—S1A—C6A9.8 (2)
C17B—C18B—C19B—C20B0.6 (7)N2A—C3A—S1A—C6A168.6 (2)
C18A—C19A—C20A—C21A0.0 (7)N1A—C6A—S1A—C3A14.77 (17)
C18B—C19B—C20B—C21B1.5 (8)C8A—C6A—S1A—C3A102.52 (18)
C19A—C20A—C21A—C22A0.7 (6)C7A—C6A—S1A—C3A132.8 (2)
C19B—C20B—C21B—C22B0.9 (7)N3B—C3B—S1B—C6B3.4 (2)
C20A—C21A—C22A—C17A0.5 (5)N2B—C3B—S1B—C6B175.3 (2)
C18A—C17A—C22A—C21A0.4 (5)N1B—C6B—S1B—C3B4.89 (16)
C16A—C17A—C22A—C21A178.1 (3)C8B—C6B—S1B—C3B112.41 (18)
C20B—C21B—C22B—C17B0.7 (7)C7B—C6B—S1B—C3B121.86 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2A—H2A···O1Bi0.861.962.815 (3)172
N2B—H2B···O1Aii0.861.962.810 (3)169
C5A—H5A2···O1Bi0.962.563.344 (4)139
C5A—H5A3···O4Ai0.962.543.477 (4)164
C12B—H12B···O2Aiii0.932.563.459 (4)161
Symmetry codes: (i) x, y1, z; (ii) x+1, y+1, z; (iii) x1, y+1, z.
 

Acknowledgements

The authors are grateful to the SAIF, IIT, Madras, India, for the data collection.

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