research papers\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

IUCrJ
Volume 10| Part 6| November 2023| Pages 694-699
ISSN: 2052-2525

Development of a scalar-based geometric parameterization approach for the crystal structure landscape of dithienylethene-based crystalline solids

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aDepartment of Chemistry, University at Buffalo, State University of New York, Buffalo, NY 14260-3000, USA, and bNSF's ChemMatCARS, University of Chicago, Chicago, Lemont, IL 60439, USA
*Correspondence e-mail: jbb6@buffalo.edu

Edited by C.-Y. Su, Sun Yat-Sen University, China (Received 1 June 2023; accepted 14 September 2023; online 26 September 2023)

Dithienylethenes (DTEs) are a promising class of organic photoswitches that can be used to create crystalline solids with properties controlled by light. However, the ability of DTEs to adopt multiple conformations, only one of which is photoactive, complicates the rational design of these materials. Herein, the synthesis and structural characterization of 19 crystalline solids containing a single DTE molecule are described. A novel DD analysis of the molecular geometries obtained from rotational potential energy surface calculations and the ensemble of experimental structures were used to construct a crystal landscape for DTE. Of the 19 crystal structures, 17 contained photoinactive DTE rotamers and only 2 were photoactive. These results highlight the challenges associated with the design of these materials. Overall, the DD analysis described herein provides rapid, effective and intuitive means of linking the molecular structure to photoactivity that could be applied more broadly to afford a general strategy for producing photoactive di­aryl­ethene-based crystalline solids.

1. Introduction

Crystal engineering is a powerful tool used to design and synthesize new materials with specific physical and chemical properties by exploiting the role that individual intermolecular interactions play when forming crystalline solids (Nangia & Desiraju, 2019[Nangia, A. K. & Desiraju, G. R. (2019). Angew. Chem. Int. Ed. 58, 4100-4107.]). Without a doubt, crystal engineering has been central to the development of crystalline materials tailored for a wide range of chemical applications including pharmaceuticals (Karimi-Jafari et al., 2018[Karimi-Jafari, M., Padrela, L., Walker, G. M. & Croker, D. M. (2018). Cryst. Growth Des. 18, 6370-6387.]; Duggirala et al., 2016[Duggirala, N. K., Perry, M. L., Almarsson, Ö. & Zaworotko, M. J. (2016). Chem. Commun. 52, 640-655.]; Guo et al., 2021[Guo, M., Sun, X., Chen, J. & Cai, T. (2021). Acta Pharm. Sin. B, 11, 2537-2564.]), biosensors (Fu et al., 2023[Fu, X., Ding, B. & D'Alessandro, D. (2023). Coord. Chem. Rev. 475, 214814.]), gas separation and storage (Shekhah et al., 2018[Shekhah, O., Chernikova, V., Belmabkhout, Y. & Eddaoudi, M. (2018). Crystals, 8, 412.]; Cheng et al., 2022[Cheng, Y., Datta, S. J., Zhou, S., Jia, J., Shekhah, O. & Eddaoudi, M. (2022). Chem. Soc. Rev. 51, 8300-8350.]), and electronics and optics (Kandambeth et al., 2022[Kandambeth, S., Kale, V. S., Shekhah, O., Alshareef, H. N. & Eddaoudi, M. (2022). Adv. Energy Mater. 12, 2100177.]; Jiang et al., 2021[Jiang, M., Zhen, C., Li, S., Zhang, X. & Hu, W. (2021). Front. Chem. 9, 764628.]; Dar & Rashid, 2021[Dar, A. A. & Rashid, S. (2021). CrystEngComm, 23, 8007-8026.]).

Traditionally, crystal structures are viewed as repeating patterns of atoms, molecules or ions arranged in a three-dimensional lattice. However, a particularly powerful concept in crystal engineering is to instead view the same crystal structure as a rich structural landscape in which the position of a molecule in a single crystal is a data point on this landscape (Desiraju, 2021[Desiraju, G. R. (2021). IUCrJ, 8, 148-149.]). Different crystallizing conditions can lead to the formation of different crystal structures, each with its own unique set of properties. Therefore, it is important to assess a wide variety of crystallizing conditions to produce crystalline solids (Samanta et al., 2021[Samanta, K., Samanta, J. & Natarajan, R. (2021). Cryst. Growth Des. 21, 166-190.]; Tothadi & Desiraju, 2012[Tothadi, S. & Desiraju, G. R. (2012). Phil. Trans. R. Soc. A. 370, 2900-2915.]; Singh et al., 2016[Singh, S. S., Vasantha, K. Y., Sattur, A. P. & Thakur, T. S. (2016). CrystEngComm, 18, 1740-1751.]; Ranjan et al., 2020[Ranjan, S., Devarapalli, R., Kundu, S., Saha, S., Deolka, S., Vangala, V. R. & Reddy, C. M. (2020). IUCrJ, 7, 173-183.]; Rajkumar & Desiraju, 2021[Rajkumar, M. & Desiraju, G. R. (2021). IUCrJ, 8, 178-185.]). Consequently, a wide variety of crystalline solids including polymorphs, hydrates, solvates, co-crystals and metal–organic frameworks can help deepen our understanding of how the molecule of interest is impacted by the surrounding crystalline environment and vice versa. This includes identifying supramolecular synthons and non-covalent interactions that are important in the formation of crystals, which inevitably affects the physical and chemical properties of crystalline solids, such as their solubility and melting point.

The changing crystalline environments directly impact the molecule of interest and ultimately the functionally important properties of the crystal, including water sorption (Reutzel-Edens & Bhardwaj, 2020[Reutzel-Edens, S. M. & Bhardwaj, R. M. (2020). IUCrJ, 7, 955-964.]), electronic properties (Narayanan et al., 2017[Narayanan, A., Cao, D., Frazer, L., Tayi, A. S., Blackburn, A. K., Sue, A. C. H., Ketterson, J. B., Stoddart, J. F. & Stupp, S. I. (2017). J. Am. Chem. Soc. 139, 9186-9191.]; Sun et al., 2019[Sun, L., Wang, Y., Yang, F., Zhang, X. & Hu, W. (2019). Adv. Mater. 31, 1902328.]), detonation properties (Landenberger et al., 2015[Landenberger, K. B., Bolton, O. & Matzger, A. J. (2015). J. Am. Chem. Soc. 137, 5074-5079.]; Kent et al., 2018[Kent, R. V., Wiscons, R. A., Sharon, P., Grinstein, D., Frimer, A. A. & Matzger, A. J. (2018). Cryst. Growth Des. 18, 219-224.]; Aakeröy et al., 2015[Aakeröy, C. B., Wijethunga, T. K. & Desper, J. (2015b). Chem. Eur. J. 21, 11029-11037.]b) and thermal stability (Aakeröy et al., 2015a[Aakeröy, C. B., Wijethunga, T. K., Benton, J. & Desper, J. (2015a). Chem. Commun. 51, 2425-2428.]; Angevine et al., 2022b[Angevine, D. J., Camacho, K. J., Rzayev, J. & Benedict, J. B. (2022b). CrystEngComm, 24, 6155-6164.],a[Angevine, D. J., Camacho, K. J., Rzayev, J. & Benedict, J. B. (2022a). Cryst. Growth Des. 22, 1594-1603.]) among others. Likewise, photoactivity in the solid state is another property heavily influenced by crystal structure (Yelgaonkar et al., 2020[Yelgaonkar, S. P., Campillo-Alvarado, G. & MacGillivray, L. R. (2020). J. Am. Chem. Soc. 142, 20772-20777.]; Campillo-Alvarado et al., 2020[Campillo-Alvarado, G., Li, C., Feng, Z., Hutchins, K. M., Swenson, D. C., Höpfl, H., Morales-Rojas, H. & MacGillivray, L. R. (2020). Organometallics, 39, 2197-2201.]; Borchers et al., 2022[Borchers, T. H., Topić, F., Christopherson, J. C., Bushuyev, O. S., Vainauskas, J., Titi, H. M., Friščić, T. & Barrett, C. J. (2022). Nat. Chem. 14, 574-581.]).

Dithienylethenes (DTEs) are a promising class of molecules for use in organic solid-state photoswitches. DTEs are attractive because they are solid-state reactive, both isomers are thermally stable and they are fatigue resistant (Fukaminato et al., 2001[Fukaminato, T., Kobatake, S., Kawai, T. & Irie, M. (2001). Proc. Jpn. Acad. Ser. B, 77, 30-35.]; Herder et al., 2015[Herder, M., Schmidt, B. M., Grubert, L., Pätzel, M., Schwarz, J. & Hecht, S. (2015). J. Am. Chem. Soc. 137, 2738-2747.]; Kitagawa et al., 2013[Kitagawa, D., Nishi, H. & Kobatake, S. (2013). Angew. Chem. Int. Ed. 52, 9320-9322.]; Kobatake et al., 2000[Kobatake, S., Shibata, K., Uchida, K. & Irie, M. (2000). J. Am. Chem. Soc. 122, 12135-12141.], 2002[Kobatake, S., Uchida, K., Tsuchida, E. & Irie, M. (2002). Chem. Commun. pp. 2804-2805.], 2007[Kobatake, S., Takami, S., Muto, H., Ishikawa, T. & Irie, M. (2007). Nature, 446, 778-781.]; Shibata et al., 2002[Shibata, K., Muto, K., Kobatake, S. & Irie, M. (2002). J. Phys. Chem. A, 106, 209-214.]). However, the rational design process for DTE-based crystalline solids is complicated by their conformational flexibility. The two thio­phene rings can rotate around the central ethyl­ene bridge, which gives rise to parallel and anti-parallel rotational isomers (Zhang & Tian, 2018[Zhang, J. & Tian, H. (2018). Adv. Opt. Mater. 6, 1701278.]; Rice et al., 2020[Rice, A. M., Martin, C. R., Galitskiy, V. A., Berseneva, A. A., Leith, G. A. & Shustova, N. B. (2020). Chem. Rev. 120, 8790-8813.]; Cox et al., 2016[Cox, J. M., Walton, I. M. & Benedict, J. B. (2016). J. Mater. Chem. C. 4, 4028-4033.]). DTE molecules are considered to be potentially photoactive in the solid state when they adopt the antiparallel geometry and have an interatomic distance between the two active carbon atoms of less than 4.2 Å (see infra) (Kobatake et al., 2002[Kobatake, S., Uchida, K., Tsuchida, E. & Irie, M. (2002). Chem. Commun. pp. 2804-2805.]). If neither of these conditions are met, the molecule is not expected to be photoactive. That said, the geometry of the DTEs within the crystalline structure profoundly affects their functionality as a photoswitch. Thus, the development and assessment of the crystal structure landscape for these materials will play a critical role in the rational design of future DTE-based materials with desired molecular geometries.

Herein we report the synthesis of (Z)-1,2-bis­(2-methyl-5-(pyridin-4-yl)thio­phen-3-yl)-1,2-di­phenyl­ethene (DTE), a bulky acyclic DTE molecule with a pyridyl functionalized thio­phene pendant groups (Fig. 1[link]). We incorporated DTE into 19 different crystalline solids such as polymorphs, co-crystals, coordination polymers and metal–organic frameworks. Single-crystal X-ray diffraction (SCXRD) analysis revealed that only 2 of the 19 crystal structures contained DTE in the photoactive geometry. These findings led to the development of a novel scalar-based approach to parametrizing the DTE geometry, which may be applied more broadly to this class of photoactive molecules.

[Figure 1]
Figure 1
Chemical structure of (Z)-1,2-bis­(2-methyl-5-(pyridin-4-yl)thio­phen-3-yl)-1,2-di­phenyl­ethene (DTE).

2. Methods

2.1. Synthesis and characterization

All reagents were purchased from commercial sources and used as received unless otherwise noted. 1H NMR spectra were obtained on a Varian Inova-400 or Varian Inova-500 operating at 400 and 500 MHz, respectively. 1H NMR peaks are referenced to residual solvent signals in CDCl3 at 7.26 p.p.m. (Gottlieb et al., 1997[Gottlieb, H. E., Kotlyar, V. & Nudelman, A. (1997). J. Org. Chem. 62, 7512-7515.]). SCXRD data were collected on a rotating anode source or using synchrotron radiation. Full details of the synthesis and characterization are provided in the supporting information (Fig. S1) which includes a detailed list of co-formers and linkers used for synthesizing crystals (Fig. S2).

2.2. Nomenclature

Each of the 19 crystal structures comprise one or two crystallographically unique DTEs. The following naming convention will be used to differentiate between these structures and their crystallographically unique DTEs. Each crystal structure is assigned a number X and labelled DTE-[X]. If DTE-[X] has one crystallographically unique DTE in the asymmetric unit, DTE itself will be referred to as DTE-X. If DTE-[X] has two crystallographically unique DTEs in the asymmetric unit, DTE-Xa or DTE-Xb will be used to refer to individual DTEs, while DTE-Xa/b will be used to refer to both DTEs.

2.3. Computational methods

All calculations were performed using density functional theory (DFT) with the computational software suite Gaussian09 (Revision D.01; Frisch et al., 2013[Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G. A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H. P., Izmaylov, A. F., Bloino, J., Zheng, G., Sonnenberg, J. L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, J. A., Peralta, J. E., Ogliaro, F., Bearpark, M., Heyd, J. J., Brothers, E., Kudin, K. N., Staroverov, V. N., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J. C., Iyengar, S. S., Tomasi, J., Cossi, M., Rega, N., Millam, J. M., Klene, M., Knox, J. E., Cross, J. B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R. E., Yazyev, O., Austin, A. J., Cammi, R., Pomelli, C., Ochterski, J. W., Martin, R. L., Morokuma, K., Zakrzewski, V. G., Voth, G. A., Salvador, P., Dannenberg, J. J., Dapprich, S., Daniels, A. D., Farkas, Ö., Foresman, J. B., Ortiz, J. V., Cioslowski, J. & Fox, D. J. (2013). Gaussian 09 Revision D.01. Gaussian Inc., Wallingford, CT, USA.]). The hybrid functional ωB97X-D with the 6-31G(d) basis set was used for all calculations (Chai & Head-Gordon, 2008[Chai, J.-D. & Head-Gordon, M. (2008). Phys. Chem. Chem. Phys. 10, 6615-6620.]). DTE and the methyl-substituted variation were geometry optimized in the anti-active geometry. The vibrational frequencies of each optimized DTE were calculated to verify that each geometry was a true energetic minimum.

Relaxed potential energy surface (RPES) scans were performed on the optimized DTE and its methyl-substituted variant. The torsion angle ΦA[C18, C1, C8, C11] was rotated by ±1° increments creating a clockwise (CW, −1°, negative) or counter-clockwise (CCW, +1°, positive) rotation about the C1—C8 bond (Fig. 1[link]). After each 1° increment, a geometry optimization was performed on the molecule while keeping ΦA rigid. These rotation and geometry optimization processes were performed in succession until all values of ΦA within ±180° were examined for a total of 360°. All resulting energies were converted from Hartree to kcal mol−1.

In addition to ΦA, three other parameters were used to assess the geometries of DTE (Fig. 2[link]): the relative orientation of methyl groups at the active carbon atoms (ΦB), the interatomic distance between the active carbon atoms (Dactive) and the interatomic distance between the methyl carbon atoms bonded to the active carbon atoms (DMe-Me). The relative orientation of methyl groups at the active carbon atoms is defined as the torsion angle ΦB[C12, C11, C28, C29]. Dactive is defined as the interatomic distance between carbon atoms C11 and C28. DMe-Me is defined as the interatomic distance between carbon atoms C12 and C29.

[Figure 2]
Figure 2
Representation of DTE identifying the atoms used to calculate the parameters φA (orange solid line), φB (green solid line), DMe-Me (red dash line) and Dactive (purple dash line).

3. Results and discussion

3.1. Summary of crystal structures obtained

A total of 19 DTE-[1–19] single crystals containing DTE were analysed using SCXRD. Two neat crystal structures of DTE (DTE-[1,2]) are polymorphs. Four crystal structures (DTE-[3–6]) are co-crystals with multitopic carb­oxy­lic acids. Four crystal structures (DTE-[7–10]) are isostructural coordination polymers with the metals cobalt, nickel, zinc and cadmium. Crystal structures DTE-[11,12] are two unique coordination polymers with copper coordinated to iodine and bromine, respectively. The remaining crystal structures (DTE-[13–19]) were produced from MOF syntheses in which zinc and DTE were solvothermally reacted with various multitopic carb­oxy­lic acids. Five of the crystal structures (DTE-[3,4,6,14,15]) possess two crystallographically unique DTEs. Altogether, the present work includes a total of 24 unique DTE geometries arising from 19 crystal structures. By visual inspection, 6 of the molecules (DTE-4a/b,5,6a/b,11) were assigned to the P3/P4 conformation. A total of 16 molecules, DTE-1,2,3a/b,7–10,12,13,14a/b,15a/b,16,17, were assigned the AP2 conformation, and the two remaining molecules, DTE-18,19, were assigned the AP1 conformation. The conformer assignments and structural parameters for the experimental DTE geometries are provided in Table S1 of the supporting information. Additionally, the photoactivity of each crystal structure was confirmed by irradiating a single crystal with UV light. The single crystal was deemed photoactive if it showed any observable colour change, otherwise it was deemed photoinactive.

3.2. Relaxed potential energy scan

The RPES plot for DTE reveals eight energetic minima and eight energetic maxima split evenly between each scan direction [Fig. 3[link](b)]. The four sets of energetic minima correspond to four discrete conformers: two conformers with antiparallel geometry (DTE-AP1 and DTE-AP2) and two conformers with parallel geometry (DTE-P3 and DTE-P4). Fig. 3[link](a) depicts each geometry from 2 different perspectives. The orientation of the vectors [\overrightarrow {\rm C11\,C12}] and [\overrightarrow {\rm C28\,C29}] characterizes each geometry. The antiparallel geometry is characterized by the two vectors pointing in approximately opposite directions, whereas the parallel geometry occurs when two vectors point in a similar direction.

[Figure 3]
Figure 3
(a) The four (+)-DTE conformers viewed from front and side perspectives. (b) RPES plot for DTE. Filled shapes represent +1° increments, while empty shapes represent −1° increments. AP1 (black, square), AP2 (red, circle), P3 (green, triangle) and P4 (blue, diamond).

The torsion angles (ΦA) and energies relative to the lowest-energy conformer DTE-P3 (ΔE) are summarized in Table 1[link]. These four conformers will be used to analyse the conformers observed in the single-crystal structures.

Table 1
Relative energy (ΔE) and selected structural parameters for DTE RPES scans

Conformer ΔE (kcal mol−1) ΦA (°) ΦB (°) Dactive (Å) DMe-Me (Å)
(+)DTE-AP1 1.11 51.46 173.76 3.45 4.47
(+)DTE-AP2 2.04 127.46 −84.97 5.19 7.25
(+)DTE-P3 0.00 −133.54 −29.77 3.87 3.91
(+)DTE-P4 0.04 −55.54 30.42 3.86 3.90
(−)DTE-AP1 1.11 51.46 173.76 3.45 4.47
(−)DTE-AP2 1.89 132.46 −94.49 5.18 7.22
(−)DTE-P3 0.00 −133.54 −29.91 3.87 3.91
(−)DTE-P4 1.87 −54.54 37.95 3.97 3.92

The DTE-AP1 and DTE-AP2 conformers can be interconverted by rotating each thienyl moiety in the same direction. This concerted rotation of the thienyl moieties results in ΦA increasing from 51.46° for DTE-AP1 to 127.46° for DTE-AP2. Consequently, Dactive also increases during this process from 3.45 Å for DTE-AP1 to 5.19 Å for DTE-AP2. The photoactivity of dithienylethenes is well established and requires the antiparallel geometry and for Dactive to be less than 4.2 Å. Though DTE-AP1 and DTE-AP2 have the correct geometry necessary to be photoactive, only DTE-AP1 is potentially photoactive (Dactive = 3.45 Å). This indicates that Dactive is the most significant distinction in photoactivity between the two antiparallel conformers. The two parallel conformers can be interconverted in a similar way to the two antiparallel conformers. Although Dactive is less than 4.2 Å for the two parallel conformers (DTE-P3 and DTE-P4), their geometry prohibits any photoactivity.

The energy differences between each scan direction are 0.00 kcal mol−1 for DTE-AP1, 0.15 kcal mol−1 for DTE-AP2, 0.00 kcal mol−1 for DTE-P3 and 1.83 kcal mol−1 for DTE-P4. The larger energy difference between each scan direction for DTE-P4 is caused by a difference in the degree of planarity between the pyridyl rings and thio­phene rings (Fig. S3).

An RPES scan on a similar molecule in which the pyridyl rings were substituted with methyl groups resulted in no significant scan-dependent differences in energy for any of the conformers (Table S2, Fig. S4). Furthermore, the ΔE values for the two methyl-substituted parallel conformers (P3 and P4) were almost identical at ∼0.36 kcal mol−1. Thus, the DTE-P3 and DTE-P4 conformers will be generally described as a singular species of quasi-enantiomers and labelled DTE-P3/P4.

The increase in energy of each conformer as they approach their respective energetic maximum is caused by an increasingly unfavourable steric interaction between the phenyl rings on the backbone and the methyl group bonded to the active carbon. This interaction is seen as the phenyl rings and methyl groups rotating in a concerted effort to reduce their interaction with each other. Smaller energetic barriers are observed between the anti–anti and para–para rotamers, whereas the larger barriers are observed between the anti–para and para–anti geometries.

3.3. DTE scalar-based parameterization

The DTE conformer type is critically important to the photoactivity of a crystalline solid and has been traditionally assigned by visually inspecting the DTE molecule itself. However, this method can be time-consuming and subjective. To address this issue, we developed a series of DTE parameters (Dactive, DMe-Me and ΦB) that can be quickly calculated and used to unambiguously determine the conformer type and visualize the crystal landscape.

The first parameter, Dactive, provides some information, but it is not enough information to unambiguously determine the type of conformer. As mentioned earlier, the photoactivity of DTE molecules depends on both the molecular geometry and the value of Dactive. DTE molecules with Dactive > 4.2 Å are not expected to be photoactive. However, the photoactivity of DTE molecules with Dactive < 4.2 Å depends on the orientation of thio­phene rings. Thus, we attempted to combine Dactive with two different vector-based parameters that represent the orientation of the thio­phene rings such as ΦB [Fig. S5(a)]. Since enantiomeric pairs of any given DTE molecule have the same values but opposite signs, we were unable to unambiguously assign rotamers using them [Fig. S5(b)]. Therefore, the parameters for a given DTE conformer may be indistinguishable from those of the enantiomer of a different conformer [Fig. S5(c)].

The use of scalar-based parameters, namely interatomic distances, eliminates complications arising from the sign of the relative orientation of vectors. Likewise, these values are invariant to structure inversion. In other words, enantiomeric pairs will possess identical values. Therefore, we combined Dactive with another scalar-based parameter DMe-Me to describe the photoactive nature of DTE molecules. When used together, these two parameters describe how the thio­phene rings are orientated relative to each other. The plot of DMe-Me versus Dactive for the calculated DTE geometries takes on the shape of a broken ellipse (Fig. 4[link]).

[Figure 4]
Figure 4
Dactive versus DMe-Me. Filled shapes represent +1° increments, while empty shapes represent −1° increments. AP1 (square), AP2 (circle), P3 (diamond) and P4 (triangle), Experimental (orange star). Heatmap represents the relative energy ΔE (kcal mol−1).

The lowest-energy calculated structures (ΔE < 5 kcal mol−1) for each of the conformers fall into one of three distinct regions. Region I, which contains the lowest-energy AP1 conformers, is characterized by Dactive < DMe-Me and Dactive < 4.20 Å. Region II, where Dactive > DMe-Me and Dactive > 4.20 Å, contains the AP2 conformers. Region III, where DactiveDMe-Me and Dactive < 5.0 Å, comprises the P3/P4 conformers. Some overlap between regions does exist for the calculated structures. For example, the calculated structures for the two antiparallel conformers are present where 3.70 Å < Dactive < 4.70 Å and 5.20 Å < DMe-Me < 6.70 Å. However, this overlap only occurs for high-energy structures of a given conformer (ΔE > 5 kcal mol−1), and the geometries for which are unlikely to be observed in a crystalline solid.

DD analysis (DactiveDMe-Me analysis) of the crystal structures confirmed that the experimental DTE geometries were clustered into the three regions described above. As anticipated, we found that the structures containing the AP1, AP2 and P3/P4 conformers are exclusively located in regions I, II and III, respectively. In fact, it is notable that most of the experimental structures are observed near the lowest-energy calculated structures. Though crystal packing forces may lead to slight deviations from the calculated minimum structures, the observed structures agree well with the minimum energy structures for each conformer type.

4. Conclusions

We found that 17 of the 19 observed DTE crystal structures (89.5%) contained a photoinactive conformer. Of these, 13 included the AP2 rotamer and 4 included the P3/P4 rotamers. The photoactive AP1 rotamer was only observed in 2 of the 19 crystal structures (10.5%). These results highlight the challenges associated with the design and synthesis of functional DTE-based crystalline materials. These challenges can be applied more broadly to any conformationally flexible system in which a specific conformation is desired in the crystalline phase. In the present case, the desired photoactivity is directly linked to the DTE conformation, which is not easily controlled in the crystalline state.

Future work will include higher level computational methods on gas phase and solvated DTE to improve the accuracy of rotamer energies. Periodic calculations using experimental crystal structures will be challenging, as these systems are large and complex. However, these calculations could provide valuable insight into the non-covalent interactions responsible for the stabilization of a given conformer within a structure.

The DD analysis presented herein provides a rapid, effective and intuitive means of relating experimental and computational DTE geometries for the construction of the crystal landscape. The determination of the crystal landscape for this DTE, and more broadly for all di­aryl­ethenes, will provide structural insights that will link the supramolecular interactions found in crystalline solids to the observed conformers, and thus provide a basis for the rational design of next-generation photoactive crystalline materials. Crystal structure landscape analyses based on important geometric parameters and other key properties of interest will serve as an indispensable tool for the broader crystal engineering community.

5. Related literature

The following references are cited in the supporting information: Sheldrick (2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.], 2015a[Sheldrick, G. M. (2015a). Acta Cryst. A71, 3-8.],b[Sheldrick, G. M. (2015b). Acta Cryst. C71, 3-8.]); Dolomanov et al. (2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); Bruker (2013[Bruker (2013). Apex3. Bruker AXS Inc., Madison, Wallingford, CT, USA.]); Müller et al. (2006[Müller, P., Muller, P., Herbst-Irmer, R., Crystallography, I. U., o , Press, O. U., Spek, A., Schneider, T. & Sawaya, M. (2006). Crystal Structure Refinement: a Crystallographer's Guide to SHELXL. Oxford University Press.]).

Supporting information


Computing details top

For all structures, cell refinement: SAINT V8.40B (Bruker AXS, 2016); data reduction: SAINT V8.40B (Bruker AXS, 2016). Program(s) used to solve structure: SHELXT 2018/2 (Sheldrick, 2018) for dte-1, dte-2, dte-3, dte-5, dte-6, dte-8, dte-9, dte-11, dte-12, dte-14, dte-19; SHELXT (Sheldrick, 2015) for dte-4, dte-7, dte-13, dte-15, dte-16, dte-17; SHELXS (Sheldrick, 2008) for dte-10, dte-18. Program(s) used to refine structure: SHELXL 2019/2 (Sheldrick, 2015) for dte-1, dte-2, dte-3, dte-4, dte-5, dte-6, dte-7, dte-9, dte-10, dte-12, dte-13, dte-14, dte-15, dte-16, dte-17, dte-18, dte-19; XL (Sheldrick, 2008) for dte-8; SHELXL 2018/3 (Sheldrick, 2015) for dte-11. For all structures, molecular graphics: Olex2 1.5 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 1.5 (Dolomanov et al., 2009).

(dte-1) top
Crystal data top
C34H26N2S2Z = 2
Mr = 526.69F(000) = 552
Triclinic, P1Dx = 1.314 Mg m3
a = 9.4895 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.6539 (5) ÅCell parameters from 5978 reflections
c = 13.4967 (6) Åθ = 2.5–30.5°
α = 114.125 (1)°µ = 0.23 mm1
β = 100.242 (1)°T = 90 K
γ = 91.853 (1)°Prism, colourless
V = 1331.32 (10) Å30.06 × 0.04 × 0.04 mm
Data collection top
Bruker APEX-II CCD
diffractometer
5311 reflections with I > 2σ(I)
φ and ω scansRint = 0.044
Absorption correction: multi-scan
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0645 before and 0.0476 after correction. The Ratio of minimum to maximum transmission is 0.9487. The λ/2 correction factor is Not present.
θmax = 28.3°, θmin = 1.7°
Tmin = 0.708, Tmax = 0.746h = 1212
27314 measured reflectionsk = 1515
6607 independent reflectionsl = 1717
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.104 w = 1/[σ2(Fo2) + (0.0429P)2 + 0.7802P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
6607 reflectionsΔρmax = 0.47 e Å3
347 parametersΔρmin = 0.31 e Å3
0 restraints
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
C280.91627 (18)0.62834 (16)0.64367 (14)0.0142 (3)
S10.58835 (4)1.02666 (4)0.87103 (4)0.01439 (10)
C100.76546 (18)0.99163 (16)0.88068 (14)0.0128 (3)
C110.52011 (18)0.86946 (15)0.82114 (14)0.0129 (3)
C90.76878 (18)0.86485 (15)0.84708 (14)0.0127 (3)
H90.8560360.8271020.8468010.015*
C130.88700 (18)1.09025 (16)0.91614 (14)0.0143 (3)
C80.62978 (17)0.79315 (15)0.81222 (13)0.0119 (3)
C120.35974 (18)0.83449 (17)0.79230 (16)0.0170 (4)
H12A0.3266 (5)0.8416 (12)0.8573 (8)0.026*
H12B0.3365 (4)0.7492 (11)0.7368 (10)0.026*
H12C0.3138 (6)0.8904 (10)0.7645 (10)0.026*
C141.01583 (19)1.06155 (17)0.87984 (15)0.0180 (4)
H141.0277790.9767390.8343670.022*
C170.87903 (19)1.21650 (16)0.98366 (15)0.0175 (4)
H170.7950511.2408471.0125700.021*
C10.61018 (17)0.65304 (15)0.77249 (13)0.0116 (3)
C151.1264 (2)1.15862 (18)0.91107 (15)0.0214 (4)
H151.2134781.1368780.8862700.026*
C160.9952 (2)1.30704 (17)1.00858 (16)0.0212 (4)
H160.9861751.3928931.0531780.025*
C20.50803 (17)0.60160 (15)0.82062 (14)0.0113 (3)
C180.68780 (17)0.58015 (15)0.69992 (13)0.0111 (3)
N11.11814 (17)1.28076 (15)0.97380 (13)0.0225 (3)
C30.50885 (18)0.66158 (16)0.93420 (14)0.0138 (3)
H30.5736940.7357930.9800990.017*
C70.40814 (18)0.49477 (16)0.75445 (15)0.0144 (3)
H70.4041650.4537840.6768460.017*
C190.70010 (17)0.44391 (15)0.67251 (14)0.0127 (3)
C250.77183 (17)0.63527 (15)0.64299 (14)0.0120 (3)
C40.41591 (19)0.61379 (17)0.98055 (15)0.0164 (3)
H40.4189710.6547751.0580310.020*
C60.31463 (18)0.44817 (16)0.80146 (15)0.0171 (4)
H60.2474490.3755670.7555180.021*
C200.69596 (18)0.35851 (16)0.56270 (15)0.0153 (3)
H200.6786800.3871050.5055130.018*
C240.72781 (18)0.39981 (16)0.75531 (15)0.0159 (3)
H240.7314170.4561480.8304400.019*
C260.70911 (18)0.70216 (15)0.58098 (14)0.0131 (3)
H260.6099870.7144340.5713980.016*
C50.31820 (18)0.50631 (17)0.91450 (16)0.0172 (4)
H50.2550780.4734070.9463750.021*
C210.71666 (19)0.23264 (17)0.53585 (16)0.0197 (4)
H210.7120870.1756480.4607510.024*
C230.75014 (19)0.27408 (18)0.72857 (17)0.0207 (4)
H230.7696610.2453280.7855730.025*
C270.80506 (17)0.74678 (16)0.53679 (14)0.0132 (3)
S20.97545 (4)0.70693 (4)0.57188 (4)0.01602 (10)
C291.02376 (19)0.57089 (18)0.69953 (16)0.0205 (4)
H29A1.0876 (12)0.5358 (12)0.6552 (8)0.031*
H29B0.9768 (6)0.5094 (12)0.7115 (10)0.031*
H29C1.0725 (12)0.6323 (8)0.7660 (10)0.031*
C220.74402 (19)0.19042 (17)0.61895 (17)0.0222 (4)
H220.7585340.1045000.6009460.027*
C300.77912 (18)0.81400 (15)0.46543 (14)0.0137 (3)
C310.64090 (19)0.83757 (17)0.42852 (15)0.0173 (4)
H310.5609200.8129160.4518470.021*
C340.89056 (19)0.85427 (17)0.42800 (15)0.0180 (4)
H340.9869590.8408010.4503840.022*
C320.6210 (2)0.89704 (17)0.35775 (16)0.0199 (4)
H320.5256730.9111840.3332580.024*
C330.8596 (2)0.91400 (18)0.35802 (15)0.0205 (4)
H330.9376930.9411810.3343820.025*
N20.72787 (17)0.93605 (14)0.32147 (13)0.0205 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C280.0142 (8)0.0142 (8)0.0147 (8)0.0001 (6)0.0033 (6)0.0066 (7)
S10.0136 (2)0.00990 (19)0.0197 (2)0.00043 (15)0.00397 (16)0.00621 (17)
C100.0129 (8)0.0148 (8)0.0112 (8)0.0005 (6)0.0027 (6)0.0059 (7)
C110.0146 (8)0.0107 (7)0.0138 (8)0.0020 (6)0.0032 (6)0.0056 (6)
C90.0123 (8)0.0131 (8)0.0131 (8)0.0003 (6)0.0031 (6)0.0060 (7)
C130.0162 (8)0.0147 (8)0.0132 (8)0.0019 (6)0.0014 (6)0.0080 (7)
C80.0125 (8)0.0124 (8)0.0105 (8)0.0003 (6)0.0031 (6)0.0043 (6)
C120.0121 (8)0.0167 (8)0.0245 (9)0.0014 (6)0.0041 (7)0.0110 (7)
C140.0190 (9)0.0177 (8)0.0158 (9)0.0011 (7)0.0046 (7)0.0055 (7)
C170.0164 (8)0.0161 (8)0.0192 (9)0.0011 (7)0.0036 (7)0.0070 (7)
C10.0113 (7)0.0115 (7)0.0117 (8)0.0007 (6)0.0010 (6)0.0052 (6)
C150.0170 (9)0.0270 (10)0.0195 (9)0.0043 (7)0.0057 (7)0.0088 (8)
C160.0224 (9)0.0145 (8)0.0235 (10)0.0030 (7)0.0006 (8)0.0069 (8)
C20.0101 (7)0.0090 (7)0.0163 (8)0.0023 (6)0.0038 (6)0.0062 (6)
C180.0094 (7)0.0127 (7)0.0122 (8)0.0007 (6)0.0014 (6)0.0067 (6)
N10.0228 (8)0.0246 (8)0.0202 (8)0.0070 (7)0.0024 (7)0.0109 (7)
C30.0119 (8)0.0123 (8)0.0161 (8)0.0007 (6)0.0029 (6)0.0051 (7)
C70.0148 (8)0.0117 (8)0.0158 (8)0.0018 (6)0.0044 (7)0.0044 (7)
C190.0086 (7)0.0126 (8)0.0169 (8)0.0009 (6)0.0045 (6)0.0055 (7)
C250.0127 (8)0.0108 (7)0.0120 (8)0.0001 (6)0.0040 (6)0.0040 (6)
C40.0164 (8)0.0194 (9)0.0175 (9)0.0048 (7)0.0073 (7)0.0102 (7)
C60.0132 (8)0.0120 (8)0.0253 (10)0.0006 (6)0.0040 (7)0.0072 (7)
C200.0139 (8)0.0157 (8)0.0167 (8)0.0009 (6)0.0056 (7)0.0064 (7)
C240.0145 (8)0.0171 (8)0.0185 (9)0.0030 (7)0.0051 (7)0.0092 (7)
C260.0124 (8)0.0126 (8)0.0142 (8)0.0019 (6)0.0044 (6)0.0049 (7)
C50.0148 (8)0.0174 (8)0.0269 (10)0.0031 (7)0.0095 (7)0.0147 (8)
C210.0162 (8)0.0140 (8)0.0242 (9)0.0003 (7)0.0094 (7)0.0016 (7)
C230.0165 (9)0.0215 (9)0.0307 (10)0.0050 (7)0.0050 (8)0.0173 (8)
C270.0117 (8)0.0132 (8)0.0139 (8)0.0003 (6)0.0028 (6)0.0049 (7)
S20.01060 (19)0.0217 (2)0.0203 (2)0.00139 (16)0.00575 (16)0.01239 (18)
C290.0152 (8)0.0256 (10)0.0238 (10)0.0032 (7)0.0032 (7)0.0138 (8)
C220.0167 (9)0.0152 (9)0.0384 (11)0.0063 (7)0.0119 (8)0.0121 (8)
C300.0179 (8)0.0106 (7)0.0112 (8)0.0013 (6)0.0042 (6)0.0030 (6)
C310.0164 (8)0.0183 (8)0.0217 (9)0.0018 (7)0.0072 (7)0.0117 (7)
C340.0151 (8)0.0221 (9)0.0176 (9)0.0022 (7)0.0028 (7)0.0098 (7)
C320.0193 (9)0.0191 (9)0.0251 (10)0.0038 (7)0.0055 (7)0.0126 (8)
C330.0210 (9)0.0220 (9)0.0194 (9)0.0056 (7)0.0054 (7)0.0098 (8)
N20.0256 (8)0.0168 (7)0.0215 (8)0.0007 (6)0.0058 (7)0.0102 (7)
Geometric parameters (Å, º) top
C28—C251.374 (2)C19—C201.400 (2)
C28—S21.7259 (17)C19—C241.399 (2)
C28—C291.497 (2)C25—C261.431 (2)
S1—C101.7374 (17)C4—H40.9500
S1—C111.7287 (16)C4—C51.393 (2)
C10—C91.360 (2)C6—H60.9500
C10—C131.466 (2)C6—C51.387 (3)
C11—C81.380 (2)C20—H200.9500
C11—C121.501 (2)C20—C211.390 (2)
C9—H90.9500C24—H240.9500
C9—C81.430 (2)C24—C231.392 (2)
C13—C141.397 (2)C26—H260.9500
C13—C171.392 (2)C26—C271.368 (2)
C8—C11.489 (2)C5—H50.9500
C12—H12A0.957 (11)C21—H210.9500
C12—H12B0.957 (11)C21—C221.387 (3)
C12—H12C0.957 (11)C23—H230.9500
C14—H140.9500C23—C221.389 (3)
C14—C151.391 (2)C27—S21.7351 (17)
C17—H170.9500C27—C301.465 (2)
C17—C161.395 (2)C29—H29A0.915 (12)
C1—C21.492 (2)C29—H29B0.915 (12)
C1—C181.357 (2)C29—H29C0.915 (12)
C15—H150.9500C22—H220.9500
C15—N11.340 (3)C30—C311.395 (2)
C16—H160.9500C30—C341.395 (2)
C16—N11.332 (3)C31—H310.9500
C2—C31.399 (2)C31—C321.383 (2)
C2—C71.400 (2)C34—H340.9500
C18—C191.489 (2)C34—C331.384 (3)
C18—C251.492 (2)C32—H320.9500
C3—H30.9500C32—N21.343 (2)
C3—C41.389 (2)C33—H330.9500
C7—H70.9500C33—N21.333 (2)
C7—C61.391 (2)
C25—C28—S2110.94 (13)C28—C25—C18124.64 (15)
C25—C28—C29130.41 (16)C28—C25—C26112.35 (15)
C29—C28—S2118.58 (13)C26—C25—C18123.00 (14)
C11—S1—C1092.59 (8)C3—C4—H4119.7
C9—C10—S1110.19 (12)C3—C4—C5120.63 (16)
C9—C10—C13128.19 (16)C5—C4—H4119.7
C13—C10—S1121.57 (13)C7—C6—H6119.6
C8—C11—S1111.00 (12)C5—C6—C7120.87 (16)
C8—C11—C12129.81 (15)C5—C6—H6119.6
C12—C11—S1119.17 (12)C19—C20—H20119.4
C10—C9—H9122.8C21—C20—C19121.18 (17)
C10—C9—C8114.33 (15)C21—C20—H20119.4
C8—C9—H9122.8C19—C24—H24119.7
C14—C13—C10120.85 (16)C23—C24—C19120.56 (17)
C17—C13—C10122.35 (16)C23—C24—H24119.7
C17—C13—C14116.76 (16)C25—C26—H26123.1
C11—C8—C9111.89 (15)C27—C26—C25113.80 (15)
C11—C8—C1125.47 (15)C27—C26—H26123.1
C9—C8—C1122.64 (14)C4—C5—H5120.6
C11—C12—H12A109.5C6—C5—C4118.89 (16)
C11—C12—H12B109.5C6—C5—H5120.6
C11—C12—H12C109.5C20—C21—H21120.1
H12A—C12—H12B109.5C22—C21—C20119.84 (17)
H12A—C12—H12C109.5C22—C21—H21120.1
H12B—C12—H12C109.5C24—C23—H23119.8
C13—C14—H14120.4C22—C23—C24120.33 (17)
C15—C14—C13119.20 (17)C22—C23—H23119.8
C15—C14—H14120.4C26—C27—S2110.10 (13)
C13—C17—H17120.2C26—C27—C30129.11 (15)
C13—C17—C16119.51 (17)C30—C27—S2120.74 (12)
C16—C17—H17120.2C28—S2—C2792.79 (8)
C8—C1—C2116.38 (14)C28—C29—H29A109.5
C18—C1—C8119.90 (14)C28—C29—H29B109.5
C18—C1—C2123.66 (15)C28—C29—H29C109.5
C14—C15—H15117.8H29A—C29—H29B109.5
N1—C15—C14124.36 (18)H29A—C29—H29C109.5
N1—C15—H15117.8H29B—C29—H29C109.5
C17—C16—H16117.9C21—C22—C23119.83 (16)
N1—C16—C17124.15 (17)C21—C22—H22120.1
N1—C16—H16117.9C23—C22—H22120.1
C3—C2—C1120.03 (14)C31—C30—C27121.71 (15)
C3—C2—C7118.35 (15)C34—C30—C27121.78 (16)
C7—C2—C1121.62 (15)C34—C30—C31116.48 (16)
C1—C18—C19124.45 (15)C30—C31—H31120.2
C1—C18—C25120.60 (14)C32—C31—C30119.62 (16)
C19—C18—C25114.93 (14)C32—C31—H31120.2
C16—N1—C15115.98 (16)C30—C34—H34120.3
C2—C3—H3119.6C33—C34—C30119.49 (17)
C4—C3—C2120.72 (16)C33—C34—H34120.3
C4—C3—H3119.6C31—C32—H32117.9
C2—C7—H7119.7N2—C32—C31124.16 (17)
C6—C7—C2120.51 (16)N2—C32—H32117.9
C6—C7—H7119.7C34—C33—H33117.7
C20—C19—C18119.98 (15)N2—C33—C34124.55 (17)
C24—C19—C18121.56 (15)N2—C33—H33117.7
C24—C19—C20118.25 (15)C33—N2—C32115.70 (16)
C28—C25—C26—C270.9 (2)C2—C7—C6—C50.0 (3)
S1—C10—C9—C80.43 (19)C18—C1—C2—C3134.97 (17)
S1—C10—C13—C14151.77 (14)C18—C1—C2—C746.1 (2)
S1—C10—C13—C1726.0 (2)C18—C19—C20—C21175.72 (15)
S1—C11—C8—C90.32 (18)C18—C19—C24—C23174.91 (16)
S1—C11—C8—C1179.80 (13)C18—C25—C26—C27179.04 (15)
C10—S1—C11—C80.07 (13)C3—C2—C7—C61.5 (2)
C10—S1—C11—C12178.80 (14)C3—C4—C5—C60.4 (3)
C10—C9—C8—C110.5 (2)C7—C2—C3—C42.0 (2)
C10—C9—C8—C1179.99 (15)C7—C6—C5—C40.9 (3)
C10—C13—C14—C15177.04 (16)C19—C18—C25—C2852.5 (2)
C10—C13—C17—C16175.87 (16)C19—C18—C25—C26127.57 (16)
C11—S1—C10—C90.21 (13)C19—C20—C21—C220.9 (3)
C11—S1—C10—C13177.33 (14)C19—C24—C23—C220.5 (3)
C11—C8—C1—C246.9 (2)C25—C28—S2—C271.46 (14)
C11—C8—C1—C18135.76 (18)C25—C18—C19—C2042.2 (2)
C9—C10—C13—C1425.3 (3)C25—C18—C19—C24132.44 (16)
C9—C10—C13—C17156.96 (18)C25—C26—C27—S20.21 (19)
C9—C8—C1—C2132.54 (16)C25—C26—C27—C30177.14 (16)
C9—C8—C1—C1844.8 (2)C20—C19—C24—C230.2 (2)
C13—C10—C9—C8176.89 (16)C20—C21—C22—C230.2 (3)
C13—C14—C15—N10.8 (3)C24—C19—C20—C210.9 (2)
C13—C17—C16—N11.7 (3)C24—C23—C22—C210.5 (3)
C8—C1—C2—C342.3 (2)C26—C27—S2—C280.94 (14)
C8—C1—C2—C7136.62 (16)C26—C27—C30—C312.6 (3)
C8—C1—C18—C19166.91 (15)C26—C27—C30—C34179.45 (17)
C8—C1—C18—C2511.5 (2)C27—C30—C31—C32177.49 (16)
C12—C11—C8—C9178.87 (17)C27—C30—C34—C33178.05 (16)
C12—C11—C8—C11.7 (3)S2—C28—C25—C18178.36 (13)
C14—C13—C17—C162.0 (3)S2—C28—C25—C261.58 (19)
C14—C15—N1—C161.2 (3)S2—C27—C30—C31174.50 (14)
C17—C13—C14—C150.8 (3)S2—C27—C30—C343.4 (2)
C17—C16—N1—C150.1 (3)C29—C28—C25—C181.6 (3)
C1—C2—C3—C4179.05 (15)C29—C28—C25—C26178.36 (17)
C1—C2—C7—C6179.59 (15)C29—C28—S2—C27178.67 (14)
C1—C18—C19—C20139.29 (17)C30—C27—S2—C28176.67 (14)
C1—C18—C19—C2446.1 (2)C30—C31—C32—N20.6 (3)
C1—C18—C25—C28126.09 (18)C30—C34—C33—N20.6 (3)
C1—C18—C25—C2653.8 (2)C31—C30—C34—C330.0 (3)
C2—C1—C18—C1910.2 (3)C31—C32—N2—C330.1 (3)
C2—C1—C18—C25171.31 (15)C34—C30—C31—C320.6 (3)
C2—C3—C4—C51.1 (3)C34—C33—N2—C320.6 (3)
(dte-2) top
Crystal data top
C34H26N2S2F(000) = 1104
Mr = 526.69Dx = 1.321 Mg m3
Monoclinic, I2/aMo Kα radiation, λ = 0.71073 Å
a = 9.8916 (4) ÅCell parameters from 9978 reflections
b = 25.9653 (10) Åθ = 2.3–33.2°
c = 10.9370 (6) ŵ = 0.23 mm1
β = 109.525 (1)°T = 90 K
V = 2647.5 (2) Å3Prism, colourless
Z = 40.2 × 0.04 × 0.02 mm
Data collection top
Bruker APEX-II CCD
diffractometer
4646 reflections with I > 2σ(I)
φ and ω scansRint = 0.020
Absorption correction: multi-scan
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1226 before and 0.0326 after correction. The Ratio of minimum to maximum transmission is 0.9578. The λ/2 correction factor is Not present.
θmax = 33.2°, θmin = 1.6°
Tmin = 0.715, Tmax = 0.747h = 1515
28558 measured reflectionsk = 3939
5068 independent reflectionsl = 1616
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.094 w = 1/[σ2(Fo2) + (0.0492P)2 + 1.8517P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
5068 reflectionsΔρmax = 0.56 e Å3
220 parametersΔρmin = 0.26 e Å3
0 restraints
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)
S10.56790 (2)0.38312 (2)0.48033 (2)0.01569 (6)
C10.31529 (8)0.26358 (3)0.49148 (7)0.01159 (12)
C20.39805 (8)0.21556 (3)0.49264 (7)0.01218 (12)
C30.45934 (9)0.20691 (3)0.39582 (8)0.01690 (14)
H30.4428330.2307630.3264930.020*
C40.54421 (10)0.16363 (3)0.40048 (9)0.02052 (16)
H40.5839980.1579550.3336840.025*
C50.57112 (9)0.12866 (3)0.50233 (9)0.01877 (15)
H50.6294760.0992770.5056370.023*
C60.51151 (9)0.13721 (3)0.59939 (8)0.01670 (14)
H60.5300010.1136530.6695370.020*
C70.42503 (8)0.18005 (3)0.59432 (8)0.01462 (13)
H70.3839840.1852100.6604610.018*
C80.38456 (8)0.31192 (3)0.47037 (7)0.01121 (12)
C90.30954 (8)0.35201 (3)0.38488 (7)0.01415 (13)
H90.2102030.3502010.3359930.017*
C100.39382 (9)0.39325 (3)0.37984 (8)0.01513 (14)
C110.52860 (8)0.32343 (3)0.52868 (7)0.01290 (13)
C120.64632 (8)0.29268 (3)0.62276 (8)0.01749 (15)
H12A0.6833 (7)0.2676 (3)0.5753 (4)0.026*
H12B0.6087 (4)0.2747 (3)0.6830 (7)0.026*
H12C0.7237 (7)0.31577 (19)0.6712 (7)0.026*
C130.35327 (11)0.44062 (4)0.30369 (11)0.0257 (2)
N10.2850 (2)0.54103 (8)0.1908 (2)0.0297 (4)0.507 (2)
C140.2186 (2)0.45673 (8)0.2446 (2)0.0323 (5)0.507 (2)
H140.1416550.4344570.2425430.039*0.507 (2)
C150.1869 (3)0.50499 (9)0.1858 (3)0.0375 (6)0.507 (2)
H150.0892840.5127170.1392090.045*0.507 (2)
C160.4215 (3)0.52858 (9)0.2569 (2)0.0228 (4)0.507 (2)
H160.4935770.5534680.2619510.027*0.507 (2)
C170.4642 (2)0.48164 (7)0.3185 (2)0.0194 (3)0.507 (2)
H170.5616750.4756550.3689780.023*0.507 (2)
N1A0.2564 (3)0.52289 (8)0.1277 (2)0.0319 (5)0.493 (2)
C14A0.24258 (19)0.43237 (7)0.16842 (19)0.0212 (4)0.493 (2)
H14A0.2035620.3993670.1392660.025*0.493 (2)
C15A0.2026 (2)0.47596 (8)0.0909 (2)0.0285 (5)0.493 (2)
H15A0.1331090.4721910.0070000.034*0.493 (2)
C16A0.3538 (5)0.52685 (9)0.2451 (3)0.0321 (6)0.493 (2)
H16A0.3926820.5599550.2732380.039*0.493 (2)
C17A0.4030 (3)0.48525 (8)0.3306 (2)0.0270 (5)0.493 (2)
H17A0.4762810.4910990.4114930.032*0.493 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.01390 (9)0.01385 (9)0.01924 (10)0.00307 (6)0.00541 (7)0.00046 (6)
C10.0107 (3)0.0115 (3)0.0130 (3)0.0004 (2)0.0046 (2)0.0005 (2)
C20.0109 (3)0.0116 (3)0.0147 (3)0.0005 (2)0.0051 (2)0.0007 (2)
C30.0201 (3)0.0143 (3)0.0205 (3)0.0033 (3)0.0123 (3)0.0028 (3)
C40.0242 (4)0.0161 (3)0.0279 (4)0.0052 (3)0.0176 (3)0.0030 (3)
C50.0167 (3)0.0132 (3)0.0289 (4)0.0033 (3)0.0110 (3)0.0028 (3)
C60.0156 (3)0.0142 (3)0.0201 (3)0.0018 (3)0.0057 (3)0.0041 (3)
C70.0145 (3)0.0146 (3)0.0153 (3)0.0011 (2)0.0057 (2)0.0020 (2)
C80.0099 (3)0.0115 (3)0.0128 (3)0.0008 (2)0.0046 (2)0.0006 (2)
C90.0116 (3)0.0160 (3)0.0154 (3)0.0020 (2)0.0053 (2)0.0037 (2)
C100.0151 (3)0.0142 (3)0.0179 (3)0.0025 (2)0.0079 (3)0.0036 (2)
C110.0108 (3)0.0134 (3)0.0145 (3)0.0000 (2)0.0043 (2)0.0006 (2)
C120.0119 (3)0.0204 (4)0.0181 (3)0.0018 (3)0.0023 (3)0.0036 (3)
C130.0259 (4)0.0232 (4)0.0351 (5)0.0101 (3)0.0193 (4)0.0165 (4)
N10.0396 (10)0.0185 (8)0.0276 (9)0.0013 (7)0.0066 (8)0.0082 (8)
C140.0235 (9)0.0214 (9)0.0424 (12)0.0015 (7)0.0020 (8)0.0151 (8)
C150.0327 (11)0.0230 (9)0.0457 (13)0.0026 (8)0.0016 (9)0.0158 (9)
C160.0322 (11)0.0138 (8)0.0254 (9)0.0007 (8)0.0135 (9)0.0028 (6)
C170.0219 (8)0.0132 (7)0.0266 (9)0.0008 (6)0.0129 (7)0.0022 (6)
N1A0.0515 (12)0.0163 (8)0.0315 (10)0.0090 (8)0.0184 (9)0.0085 (8)
C14A0.0177 (7)0.0172 (7)0.0269 (8)0.0021 (6)0.0049 (6)0.0086 (6)
C15A0.0275 (9)0.0244 (9)0.0320 (10)0.0073 (7)0.0079 (8)0.0148 (8)
C16A0.0580 (19)0.0116 (8)0.0284 (12)0.0019 (12)0.0167 (15)0.0014 (8)
C17A0.0462 (15)0.0148 (8)0.0198 (8)0.0059 (9)0.0110 (9)0.0001 (6)
Geometric parameters (Å, º) top
S1—C101.7255 (8)C12—H12B0.977 (8)
S1—C111.7235 (8)C12—H12C0.977 (8)
C1—C1i1.3653 (14)C13—C141.339 (2)
C1—C21.4892 (10)C13—C171.499 (2)
C1—C81.4846 (10)C13—C14A1.533 (2)
C2—C31.4030 (11)C13—C17A1.255 (2)
C2—C71.3999 (11)N1—C151.336 (3)
C3—H30.9500N1—C161.341 (3)
C3—C41.3933 (11)C14—H140.9500
C4—H40.9500C14—C151.396 (3)
C4—C51.3923 (12)C15—H150.9500
C5—H50.9500C16—H160.9500
C5—C61.3936 (12)C16—C171.388 (3)
C6—H60.9500C17—H170.9500
C6—C71.3929 (11)N1A—C15A1.337 (3)
C7—H70.9500N1A—C16A1.327 (4)
C8—C91.4300 (10)C14A—H14A0.9500
C8—C111.3852 (10)C14A—C15A1.390 (3)
C9—H90.9500C15A—H15A0.9500
C9—C101.3694 (11)C16A—H16A0.9500
C10—C131.4642 (12)C16A—C17A1.405 (3)
C11—C121.5004 (11)C17A—H17A0.9500
C12—H12A0.977 (8)
C11—S1—C1093.05 (4)C11—C12—H12C109.5
C1i—C1—C2122.77 (4)H12A—C12—H12B109.5
C1i—C1—C8121.88 (4)H12A—C12—H12C109.5
C8—C1—C2115.35 (6)H12B—C12—H12C109.5
C3—C2—C1120.17 (7)C10—C13—C17118.95 (11)
C7—C2—C1121.10 (7)C10—C13—C14A113.76 (11)
C7—C2—C3118.58 (7)C14—C13—C10125.19 (12)
C2—C3—H3119.7C14—C13—C17113.87 (13)
C4—C3—C2120.57 (8)C17A—C13—C10129.11 (14)
C4—C3—H3119.7C17A—C13—C14A116.94 (14)
C3—C4—H4119.8C15—N1—C16116.13 (19)
C5—C4—C3120.47 (8)C13—C14—H14118.8
C5—C4—H4119.8C13—C14—C15122.50 (19)
C4—C5—H5120.4C15—C14—H14118.8
C4—C5—C6119.28 (7)N1—C15—C14124.2 (2)
C6—C5—H5120.4N1—C15—H15117.9
C5—C6—H6119.8C14—C15—H15117.9
C7—C6—C5120.50 (7)N1—C16—H16117.9
C7—C6—H6119.8N1—C16—C17124.1 (2)
C2—C7—H7119.7C17—C16—H16117.9
C6—C7—C2120.60 (7)C13—C17—H17120.7
C6—C7—H7119.7C16—C17—C13118.58 (19)
C9—C8—C1123.48 (7)C16—C17—H17120.7
C11—C8—C1124.61 (7)C16A—N1A—C15A116.70 (19)
C11—C8—C9111.90 (7)C13—C14A—H14A121.9
C8—C9—H9123.0C15A—C14A—C13116.14 (17)
C10—C9—C8113.94 (7)C15A—C14A—H14A121.9
C10—C9—H9123.0N1A—C15A—C14A123.7 (2)
C9—C10—S1110.27 (6)N1A—C15A—H15A118.1
C9—C10—C13128.68 (8)C14A—C15A—H15A118.1
C13—C10—S1121.05 (7)N1A—C16A—H16A117.9
C8—C11—S1110.83 (6)N1A—C16A—C17A124.2 (2)
C8—C11—C12130.09 (7)C17A—C16A—H16A117.9
C12—C11—S1119.08 (6)C13—C17A—C16A122.2 (2)
C11—C12—H12A109.5C13—C17A—H17A118.9
C11—C12—H12B109.5C16A—C17A—H17A118.9
S1—C10—C13—C14165.64 (16)C9—C8—C11—C12179.24 (8)
S1—C10—C13—C172.70 (15)C9—C10—C13—C1414.6 (2)
S1—C10—C13—C14A142.77 (10)C9—C10—C13—C17177.51 (12)
S1—C10—C13—C17A32.1 (2)C9—C10—C13—C14A37.03 (14)
C1i—C1—C2—C3133.26 (10)C9—C10—C13—C17A148.1 (2)
C1i—C1—C2—C751.31 (13)C10—S1—C11—C80.87 (6)
C1i—C1—C8—C943.96 (13)C10—S1—C11—C12179.47 (7)
C1i—C1—C8—C11137.07 (10)C10—C13—C14—C15172.5 (2)
C1—C2—C3—C4176.08 (8)C10—C13—C17—C16173.13 (16)
C1—C2—C7—C6175.18 (7)C10—C13—C14A—C15A178.65 (15)
C1—C8—C9—C10179.98 (7)C10—C13—C17A—C16A178.8 (2)
C1—C8—C11—S1179.77 (6)C11—S1—C10—C90.34 (6)
C1—C8—C11—C120.16 (13)C11—S1—C10—C13179.49 (8)
C2—C1—C8—C9136.03 (7)C11—C8—C9—C100.93 (10)
C2—C1—C8—C1142.95 (10)C13—C14—C15—N15.3 (5)
C2—C3—C4—C50.89 (14)C13—C14A—C15A—N1A0.9 (3)
C3—C2—C7—C60.32 (12)N1—C16—C17—C134.3 (3)
C3—C4—C5—C60.38 (14)C14—C13—C17—C168.3 (3)
C4—C5—C6—C70.48 (13)C15—N1—C16—C170.1 (4)
C5—C6—C7—C20.83 (12)C16—N1—C15—C140.3 (4)
C7—C2—C3—C40.53 (12)C17—C13—C14—C158.8 (3)
C8—C1—C2—C346.73 (10)N1A—C16A—C17A—C132.9 (5)
C8—C1—C2—C7128.71 (8)C14A—C13—C17A—C16A4.1 (4)
C8—C9—C10—S10.26 (9)C15A—N1A—C16A—C17A0.5 (5)
C8—C9—C10—C13179.92 (8)C16A—N1A—C15A—C14A0.3 (4)
C9—C8—C11—S11.15 (8)C17A—C13—C14A—C15A3.1 (3)
Symmetry code: (i) x+1/2, y, z+1.
(dte-3) top
Crystal data top
C34H27N2S2·C34H28N2S2·C8H5O6·C8H4O6F(000) = 1512
Mr = 1449.63Dx = 1.359 Mg m3
Monoclinic, P2/nMo Kα radiation, λ = 0.71073 Å
a = 17.1862 (6) ÅCell parameters from 9947 reflections
b = 12.2494 (4) Åθ = 2.4–27.2°
c = 18.3174 (6) ŵ = 0.20 mm1
β = 113.273 (1)°T = 90 K
V = 3542.4 (2) Å3Prism, yellow
Z = 20.2 × 0.1 × 0.04 mm
Data collection top
Bruker APEX-II CCD
diffractometer
8497 reflections with I > 2σ(I)
φ and ω scansRint = 0.059
Absorption correction: multi-scan
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1284 before and 0.0553 after correction. The Ratio of minimum to maximum transmission is 0.9360. The λ/2 correction factor is Not present.
θmax = 30.5°, θmin = 1.7°
Tmin = 0.699, Tmax = 0.747h = 2424
80900 measured reflectionsk = 1717
10820 independent reflectionsl = 2626
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.045H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.123 w = 1/[σ2(Fo2) + (0.057P)2 + 1.9404P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
10820 reflectionsΔρmax = 0.48 e Å3
496 parametersΔρmin = 0.49 e Å3
7 restraints
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)
S10.67787 (2)0.70513 (3)0.37828 (2)0.02098 (9)
N10.90453 (9)1.02391 (10)0.42293 (8)0.0241 (3)
C10.73864 (9)0.44109 (10)0.28170 (8)0.0145 (2)
C20.71834 (9)0.34031 (11)0.31612 (8)0.0155 (2)
C30.74868 (10)0.32700 (12)0.39854 (9)0.0188 (3)
H30.7844040.3811680.4325160.023*
C40.72712 (11)0.23531 (13)0.43132 (10)0.0239 (3)
H40.7487860.2266810.4873940.029*
C50.67392 (11)0.15627 (13)0.38218 (10)0.0260 (3)
H50.6587670.0938890.4044740.031*
C60.64311 (11)0.16916 (13)0.30032 (10)0.0245 (3)
H60.6067770.1152790.2665940.029*
C70.66497 (9)0.26023 (11)0.26728 (9)0.0186 (3)
H70.6435280.2681250.2111580.022*
C80.73203 (9)0.54543 (11)0.32062 (8)0.0156 (3)
C90.79362 (9)0.63032 (11)0.33762 (8)0.0172 (3)
H90.8440960.6234360.3284680.021*
C100.77315 (9)0.72252 (11)0.36831 (8)0.0176 (3)
C110.66523 (9)0.57463 (11)0.34059 (9)0.0177 (3)
C120.58623 (10)0.51355 (13)0.33076 (10)0.0235 (3)
H12A0.5528 (6)0.5564 (7)0.3492 (7)0.035*
H12B0.6006 (2)0.4487 (10)0.3598 (7)0.035*
H12C0.5559 (6)0.4975 (9)0.2771 (7)0.035*
C130.81913 (9)0.82566 (11)0.38826 (8)0.0187 (3)
C140.87476 (11)0.85512 (12)0.35292 (10)0.0237 (3)
H140.8838060.8075030.3160820.028*
C150.91652 (11)0.95413 (13)0.37201 (10)0.0256 (3)
H150.9548430.9732720.3483430.031*
C160.85206 (11)0.99723 (12)0.45773 (10)0.0255 (3)
H160.8443171.0469270.4941100.031*
C170.80875 (11)0.89942 (12)0.44229 (10)0.0243 (3)
H170.7720670.8821010.4681380.029*
S20.90675 (2)0.25485 (3)0.72623 (2)0.01972 (8)
N20.68816 (10)0.56469 (11)0.56368 (9)0.0277 (3)
C180.78207 (9)0.01740 (11)0.73700 (8)0.0154 (3)
C190.82835 (9)0.11542 (11)0.72752 (8)0.0166 (3)
C200.85540 (9)0.12003 (12)0.66490 (9)0.0195 (3)
H200.8383880.0645840.6254350.023*
C210.90683 (10)0.20462 (13)0.65963 (10)0.0252 (3)
H210.9244580.2071430.6166050.030*
C220.93232 (12)0.28536 (15)0.71744 (11)0.0319 (4)
H220.9684460.3424610.7146310.038*
C230.90498 (12)0.28279 (14)0.77965 (11)0.0298 (4)
H230.9219070.3386130.8188410.036*
C240.85300 (10)0.19864 (12)0.78436 (9)0.0208 (3)
H240.8340370.1976290.8265490.025*
C250.81330 (9)0.08867 (11)0.71911 (8)0.0158 (3)
C260.75868 (9)0.17084 (11)0.67094 (9)0.0176 (3)
H260.6995290.1603830.6425420.021*
C270.79922 (9)0.26670 (11)0.66922 (9)0.0186 (3)
C280.89669 (9)0.12228 (11)0.75182 (9)0.0175 (3)
C290.97392 (9)0.06113 (13)0.80525 (9)0.0216 (3)
H29A0.9912 (5)0.0126 (9)0.7748 (4)0.032*
H29B0.9611 (3)0.0216 (9)0.8431 (6)0.032*
H29C1.0178 (6)0.1109 (6)0.8314 (6)0.032*
C300.76112 (10)0.36883 (12)0.63095 (9)0.0210 (3)
C310.67364 (11)0.38151 (13)0.59615 (11)0.0304 (4)
H310.6377390.3219930.5950000.036*
C320.63896 (11)0.48038 (14)0.56330 (11)0.0314 (4)
H320.5791320.4885390.5400560.038*
C330.77136 (13)0.55438 (15)0.59400 (14)0.0407 (5)
H330.8052380.6148010.5922550.049*
H10.929 (3)1.089 (2)0.430 (3)0.049*0.5
H20.6659 (15)0.6339 (15)0.5463 (14)0.049*
H1A0.556 (3)0.152 (2)0.067 (3)0.049*0.5
H3B0.475 (2)0.6625 (18)0.118 (2)0.049*0.71 (3)
H4A0.677 (4)0.815 (4)0.548 (4)0.049*0.36 (4)
H6A0.322 (2)1.1022 (16)0.467 (2)0.049*0.64 (4)
C340.81024 (12)0.45822 (14)0.62809 (13)0.0369 (4)
H340.8702540.4526930.6495740.044*
O10.54130 (8)0.21739 (9)0.06672 (7)0.0239 (2)
O20.55774 (8)0.22877 (9)0.04826 (7)0.0244 (2)
O30.49579 (8)0.59962 (10)0.13366 (6)0.0234 (2)
C350.54114 (9)0.27013 (12)0.00620 (9)0.0194 (3)
C360.51986 (9)0.38895 (11)0.00321 (8)0.0165 (3)
C370.51644 (9)0.44123 (12)0.06941 (9)0.0184 (3)
H370.5277310.4010190.1168580.022*
C380.49672 (9)0.55139 (12)0.06681 (8)0.0177 (3)
O40.64074 (8)0.76402 (10)0.53206 (7)0.0262 (2)
O50.51063 (9)0.69926 (10)0.50081 (9)0.0370 (3)
O60.33176 (7)1.03259 (10)0.47268 (7)0.0268 (2)
C390.56047 (11)0.77565 (13)0.51341 (9)0.0233 (3)
C400.53082 (9)0.89270 (12)0.50820 (8)0.0188 (3)
C410.44681 (9)0.91266 (12)0.49473 (9)0.0195 (3)
H410.4102810.8529630.4914290.023*
C420.41500 (9)1.01872 (12)0.48595 (9)0.0192 (3)
H3A0.450 (2)0.574 (5)0.130 (4)0.023*0.29 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.02689 (19)0.01468 (16)0.02356 (18)0.00325 (13)0.01230 (15)0.00227 (13)
N10.0319 (7)0.0120 (5)0.0228 (6)0.0010 (5)0.0047 (5)0.0023 (5)
C10.0176 (6)0.0092 (5)0.0153 (6)0.0004 (5)0.0051 (5)0.0000 (4)
C20.0188 (6)0.0106 (6)0.0181 (6)0.0012 (5)0.0083 (5)0.0012 (5)
C30.0245 (7)0.0144 (6)0.0177 (6)0.0021 (5)0.0087 (6)0.0009 (5)
C40.0338 (8)0.0198 (7)0.0206 (7)0.0046 (6)0.0135 (6)0.0062 (6)
C50.0349 (9)0.0168 (7)0.0323 (8)0.0007 (6)0.0198 (7)0.0067 (6)
C60.0288 (8)0.0156 (7)0.0303 (8)0.0059 (6)0.0129 (7)0.0002 (6)
C70.0223 (7)0.0143 (6)0.0187 (6)0.0013 (5)0.0075 (5)0.0009 (5)
C80.0209 (6)0.0105 (6)0.0147 (6)0.0009 (5)0.0061 (5)0.0002 (5)
C90.0221 (7)0.0119 (6)0.0169 (6)0.0001 (5)0.0070 (5)0.0003 (5)
C100.0226 (7)0.0126 (6)0.0160 (6)0.0002 (5)0.0060 (5)0.0020 (5)
C110.0239 (7)0.0119 (6)0.0183 (6)0.0021 (5)0.0093 (5)0.0009 (5)
C120.0247 (7)0.0203 (7)0.0281 (8)0.0008 (6)0.0133 (6)0.0006 (6)
C130.0246 (7)0.0104 (6)0.0167 (6)0.0018 (5)0.0035 (5)0.0010 (5)
C140.0325 (8)0.0140 (6)0.0252 (7)0.0015 (6)0.0120 (6)0.0040 (6)
C150.0345 (9)0.0163 (7)0.0261 (8)0.0040 (6)0.0119 (7)0.0022 (6)
C160.0345 (8)0.0152 (7)0.0228 (7)0.0023 (6)0.0072 (6)0.0050 (6)
C170.0334 (8)0.0159 (7)0.0239 (7)0.0010 (6)0.0115 (6)0.0044 (6)
S20.02007 (17)0.01438 (16)0.02349 (18)0.00236 (12)0.00731 (14)0.00339 (13)
N20.0374 (8)0.0153 (6)0.0300 (7)0.0074 (5)0.0129 (6)0.0050 (5)
C180.0182 (6)0.0106 (6)0.0170 (6)0.0009 (5)0.0065 (5)0.0012 (5)
C190.0181 (6)0.0125 (6)0.0189 (6)0.0012 (5)0.0071 (5)0.0007 (5)
C200.0210 (7)0.0172 (6)0.0211 (7)0.0016 (5)0.0093 (6)0.0014 (5)
C210.0267 (8)0.0256 (8)0.0277 (8)0.0050 (6)0.0155 (7)0.0004 (6)
C220.0341 (9)0.0271 (8)0.0357 (9)0.0145 (7)0.0151 (8)0.0031 (7)
C230.0373 (9)0.0217 (8)0.0303 (8)0.0131 (7)0.0133 (7)0.0077 (6)
C240.0262 (7)0.0166 (6)0.0198 (7)0.0040 (5)0.0095 (6)0.0028 (5)
C250.0194 (6)0.0115 (6)0.0175 (6)0.0006 (5)0.0083 (5)0.0014 (5)
C260.0187 (6)0.0139 (6)0.0197 (7)0.0011 (5)0.0068 (5)0.0018 (5)
C270.0205 (7)0.0146 (6)0.0200 (7)0.0015 (5)0.0072 (5)0.0025 (5)
C280.0208 (7)0.0135 (6)0.0192 (6)0.0000 (5)0.0089 (5)0.0023 (5)
C290.0193 (7)0.0211 (7)0.0224 (7)0.0000 (5)0.0061 (6)0.0040 (6)
C300.0275 (7)0.0130 (6)0.0225 (7)0.0016 (5)0.0099 (6)0.0012 (5)
C310.0277 (8)0.0176 (7)0.0375 (9)0.0013 (6)0.0040 (7)0.0042 (7)
C320.0282 (8)0.0221 (8)0.0364 (9)0.0056 (6)0.0049 (7)0.0045 (7)
C330.0344 (10)0.0196 (8)0.0654 (14)0.0023 (7)0.0170 (9)0.0156 (8)
C340.0274 (9)0.0193 (8)0.0609 (13)0.0027 (6)0.0143 (8)0.0150 (8)
O10.0334 (6)0.0143 (5)0.0250 (6)0.0049 (4)0.0125 (5)0.0054 (4)
O20.0335 (6)0.0162 (5)0.0221 (5)0.0065 (4)0.0095 (5)0.0003 (4)
O30.0337 (6)0.0202 (5)0.0171 (5)0.0076 (5)0.0108 (5)0.0002 (4)
C350.0209 (7)0.0141 (6)0.0202 (7)0.0025 (5)0.0049 (5)0.0023 (5)
C360.0178 (6)0.0130 (6)0.0174 (6)0.0029 (5)0.0055 (5)0.0018 (5)
C370.0224 (7)0.0152 (6)0.0168 (6)0.0043 (5)0.0071 (5)0.0035 (5)
C380.0204 (7)0.0161 (6)0.0159 (6)0.0038 (5)0.0064 (5)0.0010 (5)
O40.0326 (6)0.0214 (6)0.0275 (6)0.0114 (5)0.0149 (5)0.0064 (5)
O50.0380 (7)0.0154 (5)0.0464 (8)0.0032 (5)0.0049 (6)0.0007 (5)
O60.0212 (5)0.0271 (6)0.0334 (6)0.0068 (4)0.0121 (5)0.0098 (5)
C390.0312 (8)0.0198 (7)0.0170 (7)0.0081 (6)0.0077 (6)0.0019 (5)
C400.0238 (7)0.0161 (6)0.0153 (6)0.0061 (5)0.0067 (5)0.0023 (5)
C410.0224 (7)0.0168 (6)0.0176 (6)0.0011 (5)0.0060 (5)0.0024 (5)
C420.0203 (7)0.0202 (7)0.0172 (6)0.0050 (5)0.0074 (5)0.0037 (5)
Geometric parameters (Å, º) top
S1—C101.7310 (15)C20—C211.390 (2)
S1—C111.7206 (14)C21—H210.9500
N1—C151.340 (2)C21—C221.387 (2)
N1—C161.334 (2)C22—H220.9500
N1—H10.884 (19)C22—C231.394 (3)
C1—C1i1.364 (3)C23—H230.9500
C1—C21.4889 (18)C23—C241.389 (2)
C1—C81.4896 (18)C24—H240.9500
C2—C31.398 (2)C25—C261.4206 (19)
C2—C71.3984 (19)C25—C281.380 (2)
C3—H30.9500C26—H260.9500
C3—C41.391 (2)C26—C271.3721 (19)
C4—H40.9500C27—C301.457 (2)
C4—C51.390 (2)C28—C291.501 (2)
C5—H50.9500C29—H29A0.940 (11)
C5—C61.388 (2)C29—H29B0.940 (11)
C6—H60.9500C29—H29C0.940 (11)
C6—C71.390 (2)C30—C311.390 (2)
C7—H70.9500C30—C341.396 (2)
C8—C91.4278 (19)C31—H310.9500
C8—C111.383 (2)C31—C321.379 (2)
C9—H90.9500C32—H320.9500
C9—C101.3681 (19)C33—H330.9500
C10—C131.4582 (19)C33—C341.376 (2)
C11—C121.497 (2)C34—H340.9500
C12—H12A0.934 (12)O1—H1A0.841 (19)
C12—H12B0.934 (12)O1—C351.2821 (18)
C12—H12C0.934 (12)O2—C351.2483 (19)
C13—C141.397 (2)O3—H3B0.851 (18)
C13—C171.403 (2)O3—C381.3654 (17)
C14—H140.9500O3—H3A0.83 (2)
C14—C151.382 (2)C35—C361.4963 (19)
C15—H150.9500C36—C371.393 (2)
C16—H160.9500C36—C38iii1.4042 (19)
C16—C171.380 (2)C37—H370.9500
C17—H170.9500C37—C381.3875 (19)
S2—C271.7326 (15)O4—H4A0.85 (2)
S2—C281.7177 (14)O4—C391.291 (2)
N2—C321.333 (2)O5—C391.227 (2)
N2—C331.320 (2)O6—H6A0.868 (19)
N2—H20.933 (16)O6—C421.3637 (18)
C18—C18ii1.363 (3)C39—C401.512 (2)
C18—C191.4878 (18)C40—C411.387 (2)
C18—C251.4908 (18)C40—C42iv1.406 (2)
C19—C201.399 (2)C41—H410.9500
C19—C241.398 (2)C41—C421.394 (2)
C20—H200.9500
C11—S1—C1092.68 (7)C22—C21—H21120.1
C15—N1—H1119 (3)C21—C22—H22120.0
C16—N1—C15119.68 (14)C21—C22—C23120.06 (15)
C16—N1—H1121 (3)C23—C22—H22120.0
C1i—C1—C2123.67 (7)C22—C23—H23120.0
C1i—C1—C8120.62 (7)C24—C23—C22120.03 (15)
C2—C1—C8115.71 (11)C24—C23—H23120.0
C3—C2—C1120.26 (12)C19—C24—H24119.7
C7—C2—C1120.99 (12)C23—C24—C19120.53 (14)
C7—C2—C3118.65 (13)C23—C24—H24119.7
C2—C3—H3119.6C26—C25—C18123.17 (12)
C4—C3—C2120.72 (14)C28—C25—C18124.53 (12)
C4—C3—H3119.6C28—C25—C26112.11 (12)
C3—C4—H4119.9C25—C26—H26123.1
C5—C4—C3120.13 (14)C27—C26—C25113.81 (13)
C5—C4—H4119.9C27—C26—H26123.1
C4—C5—H5120.2C26—C27—S2110.17 (11)
C6—C5—C4119.52 (14)C26—C27—C30127.60 (14)
C6—C5—H5120.2C30—C27—S2122.11 (11)
C5—C6—H6119.7C25—C28—S2111.28 (10)
C5—C6—C7120.56 (15)C25—C28—C29129.29 (13)
C7—C6—H6119.7C29—C28—S2119.42 (11)
C2—C7—H7119.8C28—C29—H29A109.5
C6—C7—C2120.41 (14)C28—C29—H29B109.5
C6—C7—H7119.8C28—C29—H29C109.5
C9—C8—C1122.62 (12)H29A—C29—H29B109.5
C11—C8—C1125.24 (13)H29A—C29—H29C109.5
C11—C8—C9112.06 (12)H29B—C29—H29C109.5
C8—C9—H9123.2C31—C30—C27121.04 (14)
C10—C9—C8113.69 (13)C31—C30—C34117.09 (15)
C10—C9—H9123.2C34—C30—C27121.87 (15)
C9—C10—S1110.45 (11)C30—C31—H31120.0
C9—C10—C13128.05 (14)C32—C31—C30120.07 (16)
C13—C10—S1121.45 (11)C32—C31—H31120.0
C8—C11—S1111.10 (11)N2—C32—C31120.95 (16)
C8—C11—C12130.32 (13)N2—C32—H32119.5
C12—C11—S1118.51 (11)C31—C32—H32119.5
C11—C12—H12A109.5N2—C33—H33119.2
C11—C12—H12B109.5N2—C33—C34121.60 (17)
C11—C12—H12C109.5C34—C33—H33119.2
H12A—C12—H12B109.5C30—C34—H34120.1
H12A—C12—H12C109.5C33—C34—C30119.73 (17)
H12B—C12—H12C109.5C33—C34—H34120.1
C14—C13—C10120.66 (13)C35—O1—H1A112 (4)
C14—C13—C17117.49 (14)C38—O3—H3B104 (2)
C17—C13—C10121.84 (14)C38—O3—H3A96 (5)
C13—C14—H14120.3O1—C35—C36116.03 (13)
C15—C14—C13119.42 (14)O2—C35—O1124.29 (13)
C15—C14—H14120.3O2—C35—C36119.68 (13)
N1—C15—C14121.93 (16)C37—C36—C35120.60 (13)
N1—C15—H15119.0C37—C36—C38iii119.52 (12)
C14—C15—H15119.0C38iii—C36—C35119.88 (13)
N1—C16—H16119.1C36—C37—H37119.6
N1—C16—C17121.77 (14)C38—C37—C36120.74 (13)
C17—C16—H16119.1C38—C37—H37119.6
C13—C17—H17120.2O3—C38—C36iii121.60 (13)
C16—C17—C13119.69 (15)O3—C38—C37118.64 (13)
C16—C17—H17120.2C37—C38—C36iii119.75 (13)
C28—S2—C2792.60 (7)C39—O4—H4A124 (5)
C32—N2—H2121.9 (15)C42—O6—H6A106 (3)
C33—N2—C32120.51 (15)O4—C39—C40114.80 (14)
C33—N2—H2117.4 (15)O5—C39—O4123.99 (15)
C18ii—C18—C19125.76 (8)O5—C39—C40121.22 (15)
C18ii—C18—C25119.21 (7)C41—C40—C39118.66 (14)
C19—C18—C25114.98 (11)C41—C40—C42iv119.27 (13)
C20—C19—C18119.64 (12)C42iv—C40—C39122.04 (13)
C24—C19—C18121.35 (13)C40—C41—H41119.4
C24—C19—C20118.70 (13)C40—C41—C42121.20 (14)
C19—C20—H20119.5C42—C41—H41119.4
C21—C20—C19120.91 (14)O6—C42—C40iv122.27 (13)
C21—C20—H20119.5O6—C42—C41118.21 (14)
C20—C21—H21120.1C41—C42—C40iv119.52 (13)
C22—C21—C20119.74 (15)
S1—C10—C13—C14154.72 (12)C18—C19—C24—C23172.06 (15)
S1—C10—C13—C1724.4 (2)C18—C25—C26—C27173.06 (13)
N1—C16—C17—C130.5 (2)C18—C25—C28—S2173.04 (11)
C1i—C1—C2—C3137.50 (18)C18—C25—C28—C295.3 (2)
C1i—C1—C2—C746.1 (2)C19—C18—C25—C26133.35 (14)
C1i—C1—C8—C943.5 (2)C19—C18—C25—C2852.05 (19)
C1i—C1—C8—C11132.90 (18)C19—C20—C21—C220.5 (2)
C1—C2—C3—C4177.26 (13)C20—C19—C24—C231.5 (2)
C1—C2—C7—C6176.75 (14)C20—C21—C22—C231.3 (3)
C1—C8—C9—C10175.63 (13)C21—C22—C23—C240.8 (3)
C1—C8—C11—S1175.89 (11)C22—C23—C24—C190.7 (3)
C1—C8—C11—C121.0 (2)C24—C19—C20—C211.0 (2)
C2—C1—C8—C9137.04 (14)C25—C18—C19—C2038.21 (19)
C2—C1—C8—C1146.58 (19)C25—C18—C19—C24135.29 (14)
C2—C3—C4—C50.9 (2)C25—C26—C27—S21.20 (17)
C3—C2—C7—C60.3 (2)C25—C26—C27—C30174.89 (14)
C3—C4—C5—C60.5 (2)C26—C25—C28—S22.08 (16)
C4—C5—C6—C70.0 (3)C26—C25—C28—C29179.54 (14)
C5—C6—C7—C20.1 (2)C26—C27—C30—C315.9 (3)
C7—C2—C3—C40.8 (2)C26—C27—C30—C34174.66 (17)
C8—C1—C2—C343.04 (18)C27—S2—C28—C251.21 (12)
C8—C1—C2—C7133.33 (14)C27—S2—C28—C29179.77 (12)
C8—C9—C10—S10.97 (16)C27—C30—C31—C32177.19 (17)
C8—C9—C10—C13176.53 (14)C27—C30—C34—C33177.47 (19)
C9—C8—C11—S10.83 (16)C28—S2—C27—C260.00 (12)
C9—C8—C11—C12177.70 (15)C28—S2—C27—C30176.35 (13)
C9—C10—C13—C1422.5 (2)C28—C25—C26—C272.15 (19)
C9—C10—C13—C17158.32 (15)C30—C31—C32—N20.6 (3)
C10—S1—C11—C80.25 (12)C31—C30—C34—C332.0 (3)
C10—S1—C11—C12177.53 (12)C32—N2—C33—C341.9 (3)
C10—C13—C14—C15179.00 (14)C33—N2—C32—C311.6 (3)
C10—C13—C17—C16178.36 (14)C34—C30—C31—C322.3 (3)
C11—S1—C10—C90.42 (12)O1—C35—C36—C3711.5 (2)
C11—S1—C10—C13177.27 (12)O1—C35—C36—C38iii168.60 (14)
C11—C8—C9—C101.18 (18)O2—C35—C36—C37168.14 (14)
C13—C14—C15—N10.8 (3)O2—C35—C36—C38iii11.8 (2)
C14—C13—C17—C160.8 (2)C35—C36—C37—C38179.99 (13)
C15—N1—C16—C170.6 (2)C36—C37—C38—O3178.70 (13)
C16—N1—C15—C141.2 (2)C36—C37—C38—C36iii0.1 (2)
C17—C13—C14—C150.2 (2)C38iii—C36—C37—C380.1 (2)
S2—C27—C30—C31169.77 (13)O4—C39—C40—C41174.94 (13)
S2—C27—C30—C349.7 (2)O4—C39—C40—C42iv7.1 (2)
N2—C33—C34—C300.0 (4)O5—C39—C40—C414.8 (2)
C18ii—C18—C19—C20144.55 (19)O5—C39—C40—C42iv173.10 (15)
C18ii—C18—C19—C2442.0 (3)C39—C40—C41—C42177.20 (13)
C18ii—C18—C25—C2649.2 (2)C40—C41—C42—O6179.87 (13)
C18ii—C18—C25—C28125.39 (19)C40—C41—C42—C40iv0.8 (2)
C18—C19—C20—C21172.72 (14)C42iv—C40—C41—C420.8 (2)
Symmetry codes: (i) x+3/2, y, z+1/2; (ii) x+3/2, y, z+3/2; (iii) x+1, y+1, z; (iv) x+1, y+2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1v0.88 (2)1.65 (2)2.5259 (17)170 (5)
N2—H2···O40.93 (2)1.65 (2)2.5669 (17)169 (2)
O1—H1A···N1vi0.84 (2)1.69 (2)2.5259 (17)174 (6)
O3—H3B···O2iii0.85 (2)1.78 (2)2.5642 (16)153 (3)
O4—H4A···O6iv0.85 (2)1.89 (6)2.5437 (17)132 (6)
O6—H6A···O4iv0.87 (2)1.76 (3)2.5437 (17)150 (4)
Symmetry codes: (iii) x+1, y+1, z; (iv) x+1, y+2, z+1; (v) x+3/2, y+1, z+1/2; (vi) x+3/2, y1, z+1/2.
(dte-4) top
Crystal data top
4(C34H27.5N2S2)·7(C7H5O4)Z = 1
Mr = 3184.56F(000) = 1663
Triclinic, P1Dx = 1.329 Mg m3
a = 10.602 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 16.714 (4) ÅCell parameters from 9921 reflections
c = 24.181 (5) Åθ = 2.2–25.2°
α = 71.454 (6)°µ = 0.19 mm1
β = 88.132 (6)°T = 90 K
γ = 78.607 (6)°Prism, yellow
V = 3980.4 (14) Å30.16 × 0.14 × 0.04 mm
Data collection top
Bruker APEX-II CCD
diffractometer
9836 reflections with I > 2σ(I)
φ and ω scansRint = 0.059
Absorption correction: multi-scan
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1544 before and 0.0733 after correction. The Ratio of minimum to maximum transmission is 0.7627. The λ/2 correction factor is Not present.
θmax = 24.7°, θmin = 1.3°
Tmin = 0.569, Tmax = 0.745h = 1112
37926 measured reflectionsk = 1919
13567 independent reflectionsl = 2828
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.088H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.238 w = 1/[σ2(Fo2) + (0.0813P)2 + 15.2529P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max < 0.001
13567 reflectionsΔρmax = 1.61 e Å3
1176 parametersΔρmin = 0.46 e Å3
323 restraints
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)
S10.15445 (14)0.43930 (9)0.77702 (7)0.0381 (4)
S20.23747 (12)0.71789 (8)0.73557 (6)0.0273 (3)
N10.0397 (6)0.5015 (5)0.5508 (3)0.0607 (18)
N20.3493 (4)0.9160 (3)0.51641 (18)0.0263 (9)
C10.1931 (5)0.6575 (3)0.8049 (2)0.0304 (12)
C80.1763 (5)0.5861 (3)0.7828 (2)0.0293 (12)
C90.1505 (5)0.5988 (3)0.7236 (2)0.0306 (12)
H90.1444770.6528780.6940180.037*
C100.1346 (5)0.5246 (4)0.7127 (2)0.0344 (13)
C110.1831 (5)0.5027 (3)0.8173 (3)0.0351 (13)
C120.2079 (7)0.4634 (4)0.8820 (3)0.0470 (16)
H12A0.3008720.4477150.8905630.070*
H12B0.1702360.4117830.8963440.070*
H12C0.1686150.5051270.9014390.070*
C130.1028 (5)0.5168 (4)0.6570 (3)0.0372 (14)
C140.0803 (7)0.5856 (5)0.6072 (3)0.0525 (17)
H140.0867190.6406210.6089540.063*
C150.0490 (7)0.5783 (6)0.5553 (3)0.064 (2)
H150.0334870.6281040.5217670.077*
C160.0626 (6)0.4337 (5)0.5982 (3)0.0542 (19)
H160.0553190.3795700.5948830.065*
C170.0960 (6)0.4360 (4)0.6516 (3)0.0469 (16)
H170.1140630.3849580.6841560.056*
C180.1056 (5)0.7324 (3)0.7909 (2)0.0260 (11)
C190.1240 (5)0.8094 (3)0.8061 (2)0.0255 (11)
C200.0242 (5)0.8532 (3)0.8303 (2)0.0319 (12)
H200.0556320.8345960.8364410.038*
C210.0401 (5)0.9244 (4)0.8457 (2)0.0332 (13)
H210.0277180.9532430.8632150.040*
C220.1556 (5)0.9525 (3)0.8353 (2)0.0294 (12)
H220.1665761.0015100.8450420.035*
C230.2551 (5)0.9094 (3)0.8107 (2)0.0284 (11)
H230.3343120.9288170.8037940.034*
C240.2400 (5)0.8377 (3)0.7959 (2)0.0275 (11)
H240.3084990.8083880.7790320.033*
C250.0182 (5)0.7422 (3)0.7601 (2)0.0250 (11)
C260.0540 (5)0.7991 (3)0.7033 (2)0.0243 (11)
H260.0029000.8382990.6814680.029*
C270.1691 (5)0.7927 (3)0.6827 (2)0.0223 (10)
C280.1098 (5)0.6945 (3)0.7838 (2)0.0287 (11)
C290.1106 (6)0.6297 (4)0.8429 (2)0.0379 (13)
H29A0.0860420.5715980.8398820.057*
H29B0.1971380.6373060.8583910.057*
H29C0.0491590.6377490.8691150.057*
C300.2319 (4)0.8357 (3)0.6257 (2)0.0225 (10)
C310.1981 (5)0.9114 (3)0.5873 (2)0.0259 (11)
H310.1344980.9362200.5988540.031*
C320.2571 (5)0.9483 (3)0.5339 (2)0.0273 (11)
H320.2325910.9983570.5079980.033*
C330.3863 (5)0.8450 (3)0.5522 (2)0.0273 (11)
H330.4529470.8234060.5398220.033*
C340.3286 (5)0.8042 (3)0.6061 (2)0.0268 (11)
H340.3543590.7536720.6306210.032*
C20.312 (3)0.635 (2)0.8399 (11)0.037 (4)0.64 (3)
C30.435 (2)0.6001 (17)0.8201 (10)0.052 (4)0.64 (3)
H30.4387920.5925140.7826950.062*0.64 (3)
C40.5443 (14)0.5780 (11)0.8531 (10)0.068 (4)0.64 (3)
H40.6226400.5532440.8394700.082*0.64 (3)
C50.4300 (19)0.6269 (11)0.9270 (9)0.060 (4)0.64 (3)
H50.4292770.6362330.9637920.072*0.64 (3)
C60.5425 (18)0.5913 (13)0.9069 (11)0.074 (5)0.64 (3)
H60.6197730.5755590.9299390.088*0.64 (3)
C70.3164 (17)0.6495 (13)0.8930 (9)0.046 (4)0.64 (3)
H70.2395390.6755900.9069310.055*0.64 (3)
C2A0.304 (6)0.646 (4)0.849 (2)0.037 (7)0.36 (3)
C3A0.421 (4)0.611 (3)0.8369 (14)0.043 (6)0.36 (3)
H3A0.4356810.5991520.8009710.051*0.36 (3)
C4A0.522 (3)0.591 (2)0.8786 (14)0.060 (6)0.36 (3)
H4A0.6071360.5689770.8704470.071*0.36 (3)
C5A0.494 (4)0.606 (2)0.9331 (16)0.059 (7)0.36 (3)
H5A0.5608670.5985530.9602280.071*0.36 (3)
C6A0.366 (3)0.6298 (14)0.9458 (11)0.050 (6)0.36 (3)
H6A0.3455230.6299240.9843270.060*0.36 (3)
C7A0.269 (3)0.654 (2)0.9044 (14)0.042 (6)0.36 (3)
H7A0.1824820.6745310.9123250.051*0.36 (3)
S30.17467 (12)0.20076 (8)0.79479 (6)0.0270 (3)
S40.50685 (13)0.39740 (10)0.76560 (7)0.0373 (4)
N30.0661 (4)0.1029 (3)0.6165 (2)0.0319 (11)
N40.4067 (4)0.4081 (3)0.5461 (2)0.0364 (11)
C350.5297 (5)0.0886 (4)0.8644 (2)0.0271 (11)
C360.5633 (5)0.0060 (4)0.8962 (2)0.0339 (13)
C370.4697 (6)0.0553 (4)0.9048 (2)0.0398 (14)
H370.3825880.0274420.8945900.048*
C380.4988 (7)0.1434 (4)0.9277 (3)0.0480 (16)
H380.4320650.1752970.9323620.058*
C390.6225 (7)0.1860 (5)0.9438 (3)0.0574 (19)
H390.6421210.2469500.9597640.069*
C400.7168 (7)0.1396 (5)0.9367 (3)0.063 (2)
H400.8029120.1686040.9482740.076*
C410.6899 (6)0.0506 (5)0.9128 (3)0.0500 (17)
H410.7578360.0196530.9076920.060*
C420.4038 (5)0.1190 (3)0.8301 (2)0.0261 (11)
C430.3762 (4)0.0977 (3)0.7807 (2)0.0228 (10)
H430.4357500.0598540.7656700.027*
C440.2554 (4)0.1363 (3)0.7559 (2)0.0214 (10)
C450.3024 (5)0.1742 (3)0.8436 (2)0.0275 (11)
C460.2932 (5)0.2130 (4)0.8921 (2)0.0394 (14)
H46A0.3172830.2696090.8778770.059*
H46B0.3516170.1753090.9246160.059*
H46C0.2046650.2195130.9055580.059*
C470.1906 (5)0.1259 (3)0.7073 (2)0.0256 (11)
C480.2487 (5)0.0688 (3)0.6778 (2)0.0276 (11)
H480.3332320.0364830.6892900.033*
C490.1854 (5)0.0593 (3)0.6331 (2)0.0297 (12)
H490.2268630.0209110.6133390.036*
C500.0054 (6)0.1588 (4)0.6427 (3)0.0489 (17)
H500.0791670.1900900.6299350.059*
C510.0663 (5)0.1705 (4)0.6883 (3)0.0424 (15)
H510.0225960.2096310.7069700.051*
C520.6018 (5)0.1472 (4)0.8635 (2)0.0306 (12)
C530.7149 (5)0.1311 (4)0.9034 (2)0.0386 (14)
C540.8339 (6)0.1439 (4)0.8811 (3)0.0468 (16)
H540.8428950.1633800.8399630.056*
C550.9399 (6)0.1290 (5)0.9174 (3)0.062 (2)
H551.0218830.1349790.9014510.074*
C560.9257 (7)0.1054 (6)0.9769 (3)0.079 (3)
H560.9973300.0965431.0022340.094*
C570.8070 (7)0.0948 (7)0.9994 (3)0.081 (3)
H570.7966620.0788831.0404160.098*
C580.7029 (6)0.1071 (5)0.9627 (3)0.058 (2)
H580.6217550.0987650.9788760.070*
C590.5699 (5)0.2344 (4)0.8191 (2)0.0298 (12)
C600.5488 (4)0.2454 (3)0.7599 (2)0.0261 (11)
H600.5595370.1981690.7451670.031*
C610.5117 (5)0.3288 (3)0.7249 (2)0.0289 (12)
C620.5541 (5)0.3129 (4)0.8289 (3)0.0372 (14)
C630.5718 (6)0.3318 (5)0.8842 (3)0.0532 (18)
H63A0.6633280.3294250.8908840.080*
H63B0.5408730.2889800.9168900.080*
H63C0.5228330.3893660.8811020.080*
C640.4786 (5)0.3578 (3)0.6629 (2)0.0297 (12)
C650.4901 (6)0.2990 (4)0.6322 (2)0.0370 (13)
H650.5238930.2398340.6517600.044*
C660.4539 (6)0.3245 (4)0.5750 (3)0.0390 (14)
H660.4618000.2831240.5551330.047*
C670.3955 (5)0.4676 (3)0.5727 (2)0.0327 (12)
H670.3631430.5262880.5514640.039*0.5
C680.4305 (5)0.4446 (4)0.6310 (3)0.0350 (13)
H680.4221440.4874710.6496290.042*
O10.4587 (3)0.0030 (2)0.58971 (14)0.0266 (8)
O20.5564 (4)0.1146 (3)0.56341 (18)0.0411 (10)
O30.4930 (4)0.1044 (3)0.69316 (16)0.0375 (9)
O40.7164 (5)0.1301 (4)0.6325 (3)0.0672 (15)
C690.5342 (5)0.0469 (3)0.6005 (2)0.0303 (12)
C700.5969 (5)0.0169 (4)0.6593 (2)0.0345 (13)
C710.5731 (5)0.0567 (4)0.7033 (2)0.0388 (15)
C720.6291 (6)0.0821 (5)0.7584 (3)0.0517 (19)
H720.6101290.1308020.7880980.062*
C730.7129 (7)0.0355 (7)0.7697 (4)0.075 (3)
H730.7517390.0528970.8076100.090*
C740.7414 (7)0.0339 (6)0.7285 (4)0.066 (2)
H740.8002200.0644370.7376000.079*
C750.6852 (6)0.0611 (5)0.6729 (3)0.0509 (18)
O50.0548 (3)0.8942 (2)0.48399 (15)0.0317 (8)
O60.1426 (4)0.7681 (3)0.47185 (18)0.0492 (12)
O70.1070 (3)0.9212 (2)0.57804 (15)0.0274 (8)
O80.3401 (4)0.6738 (3)0.53163 (18)0.0417 (10)
C760.1337 (5)0.8214 (3)0.4993 (2)0.0324 (12)
C770.2171 (5)0.7981 (3)0.5521 (2)0.0266 (11)
C780.1994 (5)0.8473 (3)0.5904 (2)0.0238 (11)
C790.2725 (5)0.8237 (3)0.6416 (2)0.0294 (12)
H790.2567710.8564430.6676780.035*
C800.3702 (5)0.7501 (3)0.6537 (2)0.0303 (12)
H800.4231400.7341350.6879570.036*
C810.3916 (5)0.7001 (3)0.6174 (2)0.0322 (12)
H810.4575400.6497950.6269250.039*
C820.3161 (5)0.7238 (3)0.5667 (2)0.0303 (12)
O90.6826 (4)0.5618 (2)0.55902 (17)0.0433 (10)
O100.7240 (4)0.4253 (3)0.55960 (17)0.0398 (9)
O110.7261 (4)0.5994 (2)0.64842 (19)0.0464 (11)
O120.7989 (4)0.3040 (2)0.65380 (18)0.0389 (9)
C830.7208 (5)0.4798 (4)0.5854 (3)0.0348 (13)
C840.7604 (5)0.4537 (3)0.6471 (2)0.0282 (11)
C850.7626 (5)0.5134 (3)0.6765 (2)0.0322 (12)
C860.8030 (5)0.4870 (3)0.7344 (2)0.0346 (13)
H860.8046920.5282770.7536210.042*
C870.8410 (5)0.3998 (4)0.7643 (2)0.0328 (12)
H870.8690480.3816810.8040400.039*
C880.8385 (5)0.3394 (3)0.7372 (2)0.0307 (12)
H880.8638570.2798710.7582990.037*
C890.7993 (5)0.3649 (3)0.6795 (2)0.0305 (12)
H15A1.209 (13)0.400 (6)1.010 (6)0.037*0.5
H16A0.843 (9)0.589 (8)0.974 (6)0.037*0.5
O131.1593 (17)0.5064 (9)1.0225 (5)0.063 (5)0.5
O140.9801 (13)0.6044 (9)0.9992 (6)0.072 (5)0.5
O151.1742 (9)0.3566 (7)1.0176 (4)0.061 (3)0.5
H10.009 (17)0.503 (13)0.517 (4)0.073*0.5
H20.384 (7)0.938 (5)0.4804 (15)0.073*
H3B0.027 (6)0.107 (5)0.5837 (19)0.073*
H4B0.377 (7)0.425 (5)0.5090 (14)0.073*
H3C0.467 (7)0.087 (5)0.6579 (13)0.073*
H4C0.672 (7)0.151 (5)0.601 (2)0.073*
H7B0.074 (7)0.923 (5)0.5462 (19)0.073*
H80.278 (5)0.697 (5)0.507 (3)0.073*
H110.709 (7)0.608 (5)0.6128 (13)0.073*
H120.774 (7)0.329 (5)0.6181 (13)0.073*
O160.7817 (10)0.5666 (7)0.9696 (4)0.065 (3)0.5
C901.039 (2)0.5289 (11)1.0049 (7)0.044 (4)0.5
C910.980 (2)0.4651 (12)0.9931 (9)0.066 (7)0.5
C921.0467 (15)0.3808 (12)1.0012 (7)0.052 (4)0.5
C930.9894 (12)0.3202 (9)0.9863 (6)0.067 (4)0.5
H931.0364760.2643100.9893120.080*0.5
C940.8624 (13)0.3463 (9)0.9671 (6)0.076 (5)0.5
H940.8214430.3063730.9577630.091*0.5
C950.7923 (14)0.4270 (9)0.9609 (6)0.074 (4)0.5
H950.7042650.4411630.9486150.088*0.5
C960.849 (2)0.4882 (11)0.9725 (8)0.053 (5)0.5
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0336 (8)0.0224 (7)0.0638 (10)0.0055 (6)0.0015 (7)0.0212 (7)
S20.0279 (7)0.0253 (7)0.0299 (7)0.0098 (5)0.0001 (5)0.0076 (6)
N10.048 (3)0.104 (5)0.064 (4)0.043 (4)0.024 (3)0.058 (4)
N20.024 (2)0.025 (2)0.028 (2)0.0023 (18)0.0006 (18)0.008 (2)
C10.035 (3)0.022 (3)0.034 (3)0.009 (2)0.002 (2)0.007 (2)
C80.023 (3)0.022 (3)0.046 (3)0.004 (2)0.003 (2)0.015 (2)
C90.022 (3)0.024 (3)0.049 (3)0.006 (2)0.005 (2)0.015 (3)
C100.025 (3)0.036 (3)0.048 (3)0.008 (2)0.010 (2)0.022 (3)
C110.030 (3)0.025 (3)0.052 (4)0.005 (2)0.001 (2)0.015 (3)
C120.060 (4)0.031 (3)0.048 (4)0.013 (3)0.006 (3)0.007 (3)
C130.023 (3)0.049 (4)0.053 (4)0.017 (3)0.015 (2)0.031 (3)
C140.061 (4)0.061 (5)0.052 (4)0.026 (4)0.008 (3)0.033 (4)
C150.072 (5)0.080 (6)0.061 (5)0.040 (4)0.008 (4)0.036 (4)
C160.046 (4)0.071 (5)0.078 (5)0.034 (4)0.028 (4)0.057 (5)
C170.038 (3)0.052 (4)0.069 (4)0.021 (3)0.023 (3)0.039 (4)
C180.031 (3)0.023 (3)0.026 (3)0.007 (2)0.003 (2)0.009 (2)
C190.029 (3)0.021 (3)0.026 (3)0.006 (2)0.005 (2)0.005 (2)
C200.027 (3)0.032 (3)0.040 (3)0.009 (2)0.001 (2)0.013 (3)
C210.033 (3)0.034 (3)0.034 (3)0.001 (2)0.003 (2)0.018 (3)
C220.040 (3)0.021 (3)0.030 (3)0.008 (2)0.004 (2)0.010 (2)
C230.029 (3)0.022 (3)0.034 (3)0.006 (2)0.001 (2)0.008 (2)
C240.030 (3)0.022 (3)0.028 (3)0.000 (2)0.001 (2)0.009 (2)
C250.025 (3)0.025 (3)0.030 (3)0.005 (2)0.003 (2)0.016 (2)
C260.030 (3)0.020 (3)0.027 (3)0.009 (2)0.006 (2)0.012 (2)
C270.026 (3)0.015 (2)0.028 (3)0.004 (2)0.002 (2)0.010 (2)
C280.032 (3)0.026 (3)0.031 (3)0.011 (2)0.001 (2)0.011 (2)
C290.044 (3)0.035 (3)0.031 (3)0.013 (3)0.003 (2)0.002 (3)
C300.023 (2)0.017 (2)0.027 (3)0.001 (2)0.003 (2)0.010 (2)
C310.025 (3)0.025 (3)0.030 (3)0.007 (2)0.004 (2)0.010 (2)
C320.032 (3)0.018 (3)0.032 (3)0.004 (2)0.004 (2)0.008 (2)
C330.027 (3)0.022 (3)0.033 (3)0.003 (2)0.002 (2)0.011 (2)
C340.036 (3)0.016 (2)0.031 (3)0.007 (2)0.004 (2)0.010 (2)
C20.040 (7)0.017 (8)0.058 (10)0.013 (6)0.010 (7)0.011 (6)
C30.034 (7)0.040 (7)0.084 (11)0.013 (5)0.002 (7)0.018 (8)
C40.034 (6)0.064 (8)0.112 (12)0.011 (5)0.001 (7)0.035 (8)
C50.045 (10)0.069 (9)0.076 (9)0.023 (8)0.017 (7)0.030 (7)
C60.045 (7)0.078 (9)0.109 (12)0.021 (7)0.011 (8)0.038 (10)
C70.052 (7)0.029 (6)0.055 (8)0.008 (7)0.015 (7)0.009 (6)
C2A0.040 (9)0.021 (15)0.048 (11)0.004 (10)0.017 (10)0.009 (11)
C3A0.030 (10)0.039 (13)0.054 (11)0.021 (8)0.003 (9)0.001 (10)
C4A0.041 (10)0.066 (13)0.066 (14)0.014 (10)0.016 (8)0.010 (12)
C5A0.047 (12)0.063 (14)0.071 (12)0.023 (12)0.023 (11)0.016 (11)
C6A0.053 (13)0.043 (10)0.049 (10)0.012 (10)0.023 (8)0.004 (9)
C7A0.051 (11)0.029 (9)0.045 (11)0.000 (12)0.026 (9)0.012 (9)
S30.0230 (6)0.0279 (7)0.0351 (7)0.0027 (5)0.0012 (5)0.0183 (6)
S40.0294 (7)0.0345 (8)0.0550 (9)0.0071 (6)0.0044 (6)0.0238 (7)
N30.027 (2)0.035 (3)0.041 (3)0.002 (2)0.0094 (19)0.025 (2)
N40.033 (3)0.031 (3)0.040 (3)0.004 (2)0.005 (2)0.005 (2)
C350.023 (3)0.040 (3)0.020 (2)0.008 (2)0.0003 (19)0.012 (2)
C360.030 (3)0.041 (3)0.028 (3)0.000 (3)0.002 (2)0.012 (3)
C370.038 (3)0.042 (4)0.036 (3)0.009 (3)0.006 (2)0.007 (3)
C380.062 (4)0.035 (4)0.045 (4)0.014 (3)0.003 (3)0.007 (3)
C390.069 (5)0.043 (4)0.044 (4)0.008 (4)0.004 (3)0.003 (3)
C400.051 (4)0.057 (5)0.056 (4)0.017 (4)0.006 (3)0.001 (4)
C410.035 (3)0.056 (4)0.045 (4)0.001 (3)0.005 (3)0.003 (3)
C420.024 (3)0.031 (3)0.024 (3)0.007 (2)0.000 (2)0.009 (2)
C430.020 (2)0.020 (3)0.030 (3)0.004 (2)0.000 (2)0.010 (2)
C440.022 (2)0.016 (2)0.027 (3)0.0027 (19)0.0011 (19)0.009 (2)
C450.025 (3)0.033 (3)0.030 (3)0.009 (2)0.001 (2)0.016 (2)
C460.031 (3)0.058 (4)0.041 (3)0.009 (3)0.002 (2)0.031 (3)
C470.023 (3)0.022 (3)0.032 (3)0.002 (2)0.000 (2)0.011 (2)
C480.023 (3)0.026 (3)0.035 (3)0.005 (2)0.006 (2)0.017 (2)
C490.024 (3)0.024 (3)0.042 (3)0.007 (2)0.006 (2)0.018 (2)
C500.027 (3)0.061 (4)0.066 (4)0.021 (3)0.017 (3)0.045 (4)
C510.035 (3)0.046 (4)0.051 (4)0.014 (3)0.014 (3)0.034 (3)
C520.021 (3)0.047 (3)0.026 (3)0.009 (2)0.002 (2)0.014 (2)
C530.032 (3)0.060 (4)0.027 (3)0.019 (3)0.001 (2)0.011 (3)
C540.032 (3)0.066 (4)0.037 (3)0.023 (3)0.005 (2)0.001 (3)
C550.037 (4)0.091 (6)0.049 (4)0.036 (4)0.009 (3)0.004 (4)
C560.055 (5)0.126 (8)0.050 (4)0.050 (5)0.017 (3)0.001 (5)
C570.063 (5)0.149 (9)0.033 (4)0.052 (5)0.010 (3)0.009 (5)
C580.041 (4)0.102 (6)0.033 (3)0.028 (4)0.003 (3)0.014 (4)
C590.020 (3)0.036 (3)0.039 (3)0.012 (2)0.002 (2)0.015 (3)
C600.020 (2)0.027 (3)0.034 (3)0.009 (2)0.003 (2)0.011 (2)
C610.021 (3)0.024 (3)0.044 (3)0.005 (2)0.001 (2)0.013 (2)
C620.023 (3)0.054 (4)0.046 (3)0.014 (3)0.004 (2)0.028 (3)
C630.048 (4)0.072 (5)0.057 (4)0.016 (3)0.003 (3)0.042 (4)
C640.016 (2)0.023 (3)0.047 (3)0.006 (2)0.003 (2)0.005 (2)
C650.044 (3)0.026 (3)0.033 (3)0.001 (3)0.009 (2)0.003 (2)
C660.041 (3)0.026 (3)0.045 (3)0.001 (3)0.010 (3)0.007 (3)
C670.027 (3)0.022 (3)0.043 (3)0.001 (2)0.002 (2)0.004 (2)
C680.024 (3)0.028 (3)0.051 (4)0.003 (2)0.002 (2)0.010 (3)
O10.0253 (18)0.0251 (19)0.0308 (19)0.0036 (15)0.0018 (14)0.0113 (16)
O20.043 (2)0.034 (2)0.052 (3)0.0123 (19)0.0005 (19)0.018 (2)
O30.034 (2)0.042 (2)0.029 (2)0.0045 (18)0.0015 (17)0.0079 (19)
O40.050 (3)0.058 (3)0.116 (5)0.016 (3)0.011 (3)0.053 (4)
C690.031 (3)0.023 (3)0.037 (3)0.000 (2)0.004 (2)0.013 (3)
C700.021 (3)0.045 (4)0.045 (3)0.004 (2)0.004 (2)0.031 (3)
C710.028 (3)0.050 (4)0.035 (3)0.017 (3)0.002 (2)0.023 (3)
C720.041 (4)0.065 (5)0.042 (4)0.029 (3)0.014 (3)0.028 (3)
C730.049 (4)0.119 (8)0.054 (5)0.045 (5)0.024 (4)0.060 (5)
C740.039 (4)0.102 (7)0.080 (6)0.012 (4)0.024 (4)0.074 (6)
C750.026 (3)0.056 (4)0.083 (5)0.007 (3)0.008 (3)0.048 (4)
O50.031 (2)0.028 (2)0.036 (2)0.0038 (16)0.0109 (16)0.0150 (17)
O60.064 (3)0.033 (2)0.052 (3)0.013 (2)0.026 (2)0.026 (2)
O70.0246 (18)0.0239 (19)0.033 (2)0.0012 (15)0.0044 (15)0.0116 (16)
O80.043 (2)0.031 (2)0.051 (3)0.0062 (18)0.0101 (19)0.020 (2)
C760.037 (3)0.027 (3)0.031 (3)0.001 (2)0.002 (2)0.011 (2)
C770.026 (3)0.021 (3)0.031 (3)0.003 (2)0.001 (2)0.008 (2)
C780.022 (2)0.021 (3)0.027 (3)0.004 (2)0.001 (2)0.005 (2)
C790.023 (3)0.025 (3)0.039 (3)0.007 (2)0.007 (2)0.007 (2)
C800.028 (3)0.032 (3)0.029 (3)0.010 (2)0.006 (2)0.003 (2)
C810.027 (3)0.020 (3)0.045 (3)0.001 (2)0.006 (2)0.006 (2)
C820.027 (3)0.024 (3)0.041 (3)0.006 (2)0.001 (2)0.012 (2)
O90.049 (3)0.029 (2)0.045 (2)0.0031 (19)0.0153 (19)0.0068 (19)
O100.039 (2)0.038 (2)0.047 (2)0.0036 (18)0.0024 (18)0.023 (2)
O110.066 (3)0.017 (2)0.052 (3)0.0033 (19)0.019 (2)0.010 (2)
O120.038 (2)0.025 (2)0.056 (3)0.0012 (17)0.0005 (19)0.021 (2)
C830.024 (3)0.028 (3)0.050 (3)0.002 (2)0.006 (2)0.013 (3)
C840.024 (3)0.022 (3)0.040 (3)0.002 (2)0.003 (2)0.011 (2)
C850.032 (3)0.016 (3)0.048 (3)0.003 (2)0.007 (2)0.010 (2)
C860.035 (3)0.024 (3)0.047 (3)0.004 (2)0.008 (2)0.013 (3)
C870.024 (3)0.031 (3)0.038 (3)0.005 (2)0.003 (2)0.005 (3)
C880.026 (3)0.020 (3)0.040 (3)0.001 (2)0.004 (2)0.004 (2)
C890.016 (2)0.025 (3)0.051 (3)0.001 (2)0.005 (2)0.016 (3)
O130.059 (6)0.055 (8)0.071 (12)0.004 (5)0.004 (6)0.025 (8)
O140.065 (7)0.050 (6)0.089 (12)0.000 (5)0.006 (6)0.009 (6)
O150.058 (5)0.052 (6)0.063 (6)0.017 (4)0.018 (4)0.022 (5)
O160.045 (5)0.053 (6)0.073 (7)0.012 (4)0.003 (5)0.001 (5)
C900.054 (6)0.047 (6)0.018 (8)0.000 (5)0.011 (5)0.003 (5)
C910.053 (6)0.050 (6)0.084 (19)0.011 (4)0.013 (7)0.015 (7)
C920.058 (6)0.046 (6)0.032 (10)0.010 (5)0.015 (6)0.002 (5)
C930.065 (7)0.052 (7)0.070 (9)0.015 (5)0.033 (6)0.013 (6)
C940.070 (7)0.052 (7)0.086 (11)0.013 (5)0.047 (7)0.004 (6)
C950.062 (7)0.051 (6)0.086 (11)0.003 (5)0.024 (7)0.002 (6)
C960.047 (6)0.050 (7)0.040 (12)0.003 (5)0.002 (6)0.007 (7)
Geometric parameters (Å, º) top
S1—C101.729 (6)C43—H430.9500
S1—C111.721 (6)C43—C441.376 (7)
S2—C271.733 (5)C44—C471.455 (7)
S2—C281.718 (5)C45—C461.503 (7)
N1—C151.346 (10)C46—H46A0.9800
N1—C161.319 (10)C46—H46B0.9800
N1—H10.88 (2)C46—H46C0.9800
N2—C321.342 (7)C47—C481.403 (7)
N2—C331.349 (7)C47—C511.392 (7)
N2—H20.89 (2)C48—H480.9500
C1—C81.495 (7)C48—C491.358 (7)
C1—C181.354 (7)C49—H490.9500
C1—C21.46 (3)C50—H500.9500
C1—C2A1.56 (5)C50—C511.379 (8)
C8—C91.406 (8)C51—H510.9500
C8—C111.367 (8)C52—C531.491 (7)
C9—H90.9500C52—C591.492 (8)
C9—C101.390 (7)C53—C541.385 (8)
C10—C131.448 (8)C53—C581.371 (8)
C11—C121.503 (8)C54—H540.9500
C12—H12A0.9800C54—C551.382 (8)
C12—H12B0.9800C55—H550.9500
C12—H12C0.9800C55—C561.377 (10)
C13—C141.363 (9)C56—H560.9500
C13—C171.413 (8)C56—C571.376 (10)
C14—H140.9500C57—H570.9500
C14—C151.356 (9)C57—C581.380 (9)
C15—H150.9500C58—H580.9500
C16—H160.9500C59—C601.405 (7)
C16—C171.366 (9)C59—C621.383 (8)
C17—H170.9500C60—H600.9500
C18—C191.495 (7)C60—C611.368 (7)
C18—C251.485 (7)C61—C641.451 (8)
C19—C201.387 (7)C62—C631.494 (8)
C19—C241.391 (7)C63—H63A0.9800
C20—H200.9500C63—H63B0.9800
C20—C211.396 (7)C63—H63C0.9800
C21—H210.9500C64—C651.395 (8)
C21—C221.383 (8)C64—C681.407 (7)
C22—H220.9500C65—H650.9500
C22—C231.386 (7)C65—C661.355 (8)
C23—H230.9500C66—H660.9500
C23—C241.392 (7)C67—H670.9500
C24—H240.9500C67—C681.380 (8)
C25—C261.411 (7)C68—H680.9500
C25—C281.374 (7)O1—C691.270 (6)
C26—H260.9500O2—C691.260 (7)
C26—C271.370 (7)O3—C711.351 (7)
C27—C301.450 (7)O3—H3C0.84 (2)
C28—C291.493 (7)O4—C751.344 (9)
C29—H29A0.9800O4—H4C0.84 (2)
C29—H29B0.9800C69—C701.480 (8)
C29—H29C0.9800C70—C711.407 (9)
C30—C311.415 (7)C70—C751.408 (8)
C30—C341.399 (7)C71—C721.379 (8)
C31—H310.9500C72—H720.9500
C31—C321.354 (7)C72—C731.375 (12)
C32—H320.9500C73—H730.9500
C33—H330.9500C73—C741.347 (12)
C33—C341.363 (7)C74—H740.9500
C34—H340.9500C74—C751.387 (10)
C2—C31.45 (3)O5—C761.284 (6)
C2—C71.38 (2)O6—C761.258 (6)
C3—H30.9500O7—C781.371 (6)
C3—C41.35 (2)O7—H7B0.85 (2)
C4—H40.9500O8—C821.355 (6)
C4—C61.39 (2)O8—H80.84 (2)
C5—H50.9500C76—C771.477 (7)
C5—C61.37 (2)C77—C781.407 (7)
C5—C71.40 (2)C77—C821.414 (7)
C6—H60.9500C78—C791.386 (7)
C7—H70.9500C79—H790.9500
C2A—C3A1.33 (5)C79—C801.399 (7)
C2A—C7A1.41 (4)C80—H800.9500
C3A—H3A0.9500C80—C811.380 (8)
C3A—C4A1.41 (4)C81—H810.9500
C4A—H4A0.9500C81—C821.389 (7)
C4A—C5A1.42 (4)O9—C831.300 (7)
C5A—H5A0.9500O10—C831.254 (7)
C5A—C6A1.39 (4)O11—C851.361 (6)
C6A—H6A0.9500O11—H110.85 (2)
C6A—C7A1.37 (3)O12—C891.351 (6)
C7A—H7A0.9500O12—H120.85 (2)
S3—C441.732 (5)C83—C841.463 (8)
S3—C451.720 (5)C84—C851.402 (7)
S4—C611.726 (5)C84—C891.424 (7)
S4—C621.727 (6)C85—C861.383 (8)
N3—C491.332 (6)C86—H860.9500
N3—C501.343 (7)C86—C871.388 (7)
N3—H3B0.88 (2)C87—H870.9500
N4—C661.348 (7)C87—C881.372 (8)
N4—C671.330 (7)C88—H880.9500
N4—H4B0.90 (2)C88—C891.375 (8)
C35—C361.496 (8)O13—C901.299 (14)
C35—C421.505 (7)O14—C901.260 (14)
C35—C521.351 (7)O15—H15A0.84 (2)
C36—C371.382 (8)O15—C921.366 (15)
C36—C411.404 (8)O16—H16A0.84 (2)
C37—H370.9500O16—C961.345 (17)
C37—C381.373 (8)C90—C911.445 (12)
C38—H380.9500C91—C921.403 (15)
C38—C391.366 (9)C91—C961.420 (15)
C39—H390.9500C92—C931.418 (16)
C39—C401.357 (11)C93—H930.9500
C40—H400.9500C93—C941.377 (14)
C40—C411.386 (10)C94—H940.9500
C41—H410.9500C94—C951.370 (14)
C42—C431.407 (7)C95—H950.9500
C42—C451.375 (7)C95—C961.389 (18)
C11—S1—C1092.6 (3)C43—C44—C47129.8 (4)
C28—S2—C2792.4 (2)C47—C44—S3120.1 (3)
C15—N1—H1115 (10)C42—C45—S3111.5 (4)
C16—N1—C15118.0 (6)C42—C45—C46129.0 (5)
C16—N1—H1126 (10)C46—C45—S3119.5 (4)
C32—N2—C33120.4 (4)C45—C46—H46A109.5
C32—N2—H2122 (5)C45—C46—H46B109.5
C33—N2—H2118 (5)C45—C46—H46C109.5
C8—C1—C2A121 (2)H46A—C46—H46B109.5
C18—C1—C8120.9 (5)H46A—C46—H46C109.5
C18—C1—C2127.6 (14)H46B—C46—H46C109.5
C18—C1—C2A117 (2)C48—C47—C44121.9 (4)
C2—C1—C8111.5 (13)C51—C47—C44121.9 (4)
C9—C8—C1122.7 (5)C51—C47—C48116.2 (5)
C11—C8—C1124.4 (5)C47—C48—H48119.6
C11—C8—C9112.9 (5)C49—C48—C47120.8 (5)
C8—C9—H9123.2C49—C48—H48119.6
C10—C9—C8113.5 (5)N3—C49—C48121.1 (5)
C10—C9—H9123.2N3—C49—H49119.5
C9—C10—S1109.7 (4)C48—C49—H49119.5
C9—C10—C13127.1 (6)N3—C50—H50120.2
C13—C10—S1123.2 (4)N3—C50—C51119.7 (5)
C8—C11—S1111.3 (4)C51—C50—H50120.2
C8—C11—C12129.2 (5)C47—C51—H51119.4
C12—C11—S1119.5 (4)C50—C51—C47121.1 (5)
C11—C12—H12A109.5C50—C51—H51119.4
C11—C12—H12B109.5C35—C52—C53124.8 (5)
C11—C12—H12C109.5C35—C52—C59119.0 (5)
H12A—C12—H12B109.5C53—C52—C59116.2 (5)
H12A—C12—H12C109.5C54—C53—C52120.5 (5)
H12B—C12—H12C109.5C58—C53—C52121.1 (5)
C14—C13—C10122.5 (6)C58—C53—C54118.3 (5)
C14—C13—C17116.4 (6)C53—C54—H54119.4
C17—C13—C10121.1 (6)C55—C54—C53121.3 (6)
C13—C14—H14118.8C55—C54—H54119.4
C15—C14—C13122.5 (7)C54—C55—H55120.2
C15—C14—H14118.8C56—C55—C54119.5 (6)
N1—C15—C14120.8 (8)C56—C55—H55120.2
N1—C15—H15119.6C55—C56—H56120.2
C14—C15—H15119.6C57—C56—C55119.6 (6)
N1—C16—H16117.8C57—C56—H56120.2
N1—C16—C17124.3 (7)C56—C57—H57119.8
C17—C16—H16117.8C56—C57—C58120.4 (7)
C13—C17—H17121.0C58—C57—H57119.8
C16—C17—C13118.0 (7)C53—C58—C57120.9 (6)
C16—C17—H17121.0C53—C58—H58119.5
C1—C18—C19123.4 (5)C57—C58—H58119.5
C1—C18—C25121.2 (5)C60—C59—C52121.7 (5)
C25—C18—C19115.4 (4)C62—C59—C52127.1 (5)
C20—C19—C18119.7 (5)C62—C59—C60111.2 (5)
C20—C19—C24119.7 (5)C59—C60—H60122.4
C24—C19—C18120.6 (4)C61—C60—C59115.3 (5)
C19—C20—H20119.7C61—C60—H60122.4
C19—C20—C21120.6 (5)C60—C61—S4109.8 (4)
C21—C20—H20119.7C60—C61—C64126.5 (5)
C20—C21—H21120.3C64—C61—S4123.7 (4)
C22—C21—C20119.4 (5)C59—C62—S4111.3 (4)
C22—C21—H21120.3C59—C62—C63129.5 (6)
C21—C22—H22119.9C63—C62—S4119.2 (5)
C21—C22—C23120.1 (5)C62—C63—H63A109.5
C23—C22—H22119.9C62—C63—H63B109.5
C22—C23—H23119.8C62—C63—H63C109.5
C22—C23—C24120.5 (5)H63A—C63—H63B109.5
C24—C23—H23119.8H63A—C63—H63C109.5
C19—C24—C23119.6 (5)H63B—C63—H63C109.5
C19—C24—H24120.2C65—C64—C61120.6 (5)
C23—C24—H24120.2C65—C64—C68116.4 (5)
C26—C25—C18124.5 (4)C68—C64—C61123.0 (5)
C28—C25—C18122.9 (5)C64—C65—H65119.4
C28—C25—C26112.5 (4)C66—C65—C64121.3 (5)
C25—C26—H26123.1C66—C65—H65119.4
C27—C26—C25113.8 (4)N4—C66—C65120.5 (5)
C27—C26—H26123.1N4—C66—H66119.7
C26—C27—S2110.1 (4)C65—C66—H66119.7
C26—C27—C30129.5 (5)N4—C67—H67119.8
C30—C27—S2120.4 (4)N4—C67—C68120.5 (5)
C25—C28—S2111.1 (4)C68—C67—H67119.8
C25—C28—C29129.2 (5)C64—C68—H68119.9
C29—C28—S2119.7 (4)C67—C68—C64120.2 (5)
C28—C29—H29A109.5C67—C68—H68119.9
C28—C29—H29B109.5C71—O3—H3C112 (5)
C28—C29—H29C109.5C75—O4—H4C118 (6)
H29A—C29—H29B109.5O1—C69—C70118.1 (5)
H29A—C29—H29C109.5O2—C69—O1122.6 (5)
H29B—C29—H29C109.5O2—C69—C70119.4 (5)
C31—C30—C27121.6 (4)C71—C70—C69122.2 (5)
C34—C30—C27121.5 (4)C71—C70—C75117.3 (6)
C34—C30—C31116.9 (4)C75—C70—C69120.5 (6)
C30—C31—H31120.2O3—C71—C70121.0 (5)
C32—C31—C30119.6 (5)O3—C71—C72117.6 (6)
C32—C31—H31120.2C72—C71—C70121.4 (6)
N2—C32—C31121.9 (5)C71—C72—H72120.6
N2—C32—H32119.0C73—C72—C71118.8 (8)
C31—C32—H32119.0C73—C72—H72120.6
N2—C33—H33119.9C72—C73—H73119.1
N2—C33—C34120.3 (5)C74—C73—C72121.9 (7)
C34—C33—H33119.9C74—C73—H73119.1
C30—C34—H34119.5C73—C74—H74119.9
C33—C34—C30120.9 (5)C73—C74—C75120.3 (7)
C33—C34—H34119.5C75—C74—H74119.9
C3—C2—C1122.3 (16)O4—C75—C70120.7 (6)
C7—C2—C1122 (2)O4—C75—C74119.0 (7)
C7—C2—C3115 (2)C74—C75—C70120.3 (8)
C2—C3—H3119.0C78—O7—H7B102 (5)
C4—C3—C2122.0 (17)C82—O8—H8100 (5)
C4—C3—H3119.0O5—C76—C77118.8 (5)
C3—C4—H4119.9O6—C76—O5123.0 (5)
C3—C4—C6120.2 (14)O6—C76—C77118.1 (5)
C6—C4—H4119.9C78—C77—C76121.7 (4)
C6—C5—H5120.2C78—C77—C82117.5 (5)
C6—C5—C7119.6 (16)C82—C77—C76120.8 (5)
C7—C5—H5120.2O7—C78—C77120.4 (4)
C4—C6—H6119.8O7—C78—C79117.4 (4)
C5—C6—C4120.5 (16)C79—C78—C77122.2 (5)
C5—C6—H6119.8C78—C79—H79121.0
C2—C7—C5122.4 (17)C78—C79—C80118.0 (5)
C2—C7—H7118.8C80—C79—H79121.0
C5—C7—H7118.8C79—C80—H80119.1
C3A—C2A—C1116 (3)C81—C80—C79121.8 (5)
C3A—C2A—C7A125 (4)C81—C80—H80119.1
C7A—C2A—C1117 (4)C80—C81—H81120.3
C2A—C3A—H3A121.1C80—C81—C82119.5 (5)
C2A—C3A—C4A118 (3)C82—C81—H81120.3
C4A—C3A—H3A121.1O8—C82—C77121.0 (5)
C3A—C4A—H4A120.4O8—C82—C81118.1 (5)
C3A—C4A—C5A119 (3)C81—C82—C77120.9 (5)
C5A—C4A—H4A120.4C85—O11—H11110 (5)
C4A—C5A—H5A120.6C89—O12—H12109 (5)
C6A—C5A—C4A119 (2)O9—C83—C84117.0 (5)
C6A—C5A—H5A120.6O10—C83—O9121.9 (5)
C5A—C6A—H6A119.1O10—C83—C84121.1 (5)
C7A—C6A—C5A122 (2)C85—C84—C83122.4 (5)
C7A—C6A—H6A119.1C85—C84—C89117.4 (5)
C2A—C7A—H7A121.8C89—C84—C83120.3 (5)
C6A—C7A—C2A116 (3)O11—C85—C84120.7 (5)
C6A—C7A—H7A121.8O11—C85—C86118.1 (5)
C45—S3—C4492.2 (2)C86—C85—C84121.2 (5)
C61—S4—C6292.3 (3)C85—C86—H86120.2
C49—N3—C50121.1 (4)C85—C86—C87119.6 (5)
C49—N3—H3B124 (5)C87—C86—H86120.2
C50—N3—H3B114 (5)C86—C87—H87119.6
C66—N4—H4B121 (5)C88—C87—C86120.9 (5)
C67—N4—C66121.1 (5)C88—C87—H87119.6
C67—N4—H4B118 (5)C87—C88—H88120.0
C36—C35—C42115.4 (4)C87—C88—C89120.1 (5)
C52—C35—C36126.2 (5)C89—C88—H88120.0
C52—C35—C42118.4 (5)O12—C89—C84120.3 (5)
C37—C36—C35120.0 (5)O12—C89—C88118.8 (5)
C37—C36—C41116.5 (6)C88—C89—C84120.9 (5)
C41—C36—C35123.2 (5)C92—O15—H15A111 (10)
C36—C37—H37119.0C96—O16—H16A99 (10)
C38—C37—C36121.9 (6)O13—C90—C91117.8 (12)
C38—C37—H37119.0O14—C90—O13119.1 (16)
C37—C38—H38119.6O14—C90—C91123.1 (13)
C39—C38—C37120.9 (7)C92—C91—C90122.0 (13)
C39—C38—H38119.6C92—C91—C96118.7 (15)
C38—C39—H39120.6C96—C91—C90119.2 (12)
C40—C39—C38118.8 (7)O15—C92—C91121.1 (15)
C40—C39—H39120.6O15—C92—C93117.1 (14)
C39—C40—H40119.4C91—C92—C93121.4 (13)
C39—C40—C41121.3 (7)C92—C93—H93121.5
C41—C40—H40119.4C94—C93—C92116.9 (12)
C36—C41—H41119.7C94—C93—H93121.5
C40—C41—C36120.6 (7)C93—C94—H94118.4
C40—C41—H41119.7C95—C94—C93123.2 (14)
C43—C42—C35125.4 (4)C95—C94—H94118.4
C45—C42—C35122.3 (4)C94—C95—H95119.8
C45—C42—C43112.2 (4)C94—C95—C96120.4 (14)
C42—C43—H43123.0C96—C95—H95119.8
C44—C43—C42114.1 (4)O16—C96—C91118.7 (16)
C44—C43—H43123.0O16—C96—C95121.8 (18)
C43—C44—S3110.0 (3)C95—C96—C91119.2 (15)
S1—C10—C13—C14176.2 (5)C42—C35—C52—C5913.4 (7)
S1—C10—C13—C175.0 (7)C42—C43—C44—S30.2 (6)
S2—C27—C30—C31163.6 (4)C42—C43—C44—C47175.8 (5)
S2—C27—C30—C3416.5 (6)C43—C42—C45—S30.9 (6)
N1—C16—C17—C132.0 (9)C43—C42—C45—C46179.2 (5)
N2—C33—C34—C301.2 (7)C43—C44—C47—C481.0 (9)
C1—C8—C9—C10178.2 (5)C43—C44—C47—C51179.5 (6)
C1—C8—C11—S1178.3 (4)C44—S3—C45—C420.8 (4)
C1—C8—C11—C120.1 (9)C44—S3—C45—C46179.3 (5)
C1—C18—C19—C20133.6 (6)C44—C47—C48—C49179.0 (5)
C1—C18—C19—C2446.7 (7)C44—C47—C51—C50178.9 (6)
C1—C18—C25—C26115.3 (6)C45—S3—C44—C430.6 (4)
C1—C18—C25—C2863.1 (7)C45—S3—C44—C47175.9 (4)
C1—C2—C3—C4179 (3)C45—C42—C43—C440.5 (7)
C1—C2—C7—C5179 (2)C47—C48—C49—N30.9 (9)
C1—C2A—C3A—C4A174 (4)C48—C47—C51—C500.4 (9)
C1—C2A—C7A—C6A170 (4)C49—N3—C50—C511.1 (10)
C8—C1—C18—C19173.2 (5)C50—N3—C49—C481.2 (9)
C8—C1—C18—C258.4 (8)C51—C47—C48—C490.5 (8)
C8—C1—C2—C349 (3)C52—C35—C36—C37165.0 (5)
C8—C1—C2—C7134 (3)C52—C35—C36—C4122.3 (8)
C8—C1—C2A—C3A48 (6)C52—C35—C42—C43113.1 (6)
C8—C1—C2A—C7A118 (4)C52—C35—C42—C4565.0 (7)
C8—C9—C10—S10.7 (6)C52—C53—C54—C55179.7 (7)
C8—C9—C10—C13177.7 (5)C52—C53—C58—C57178.1 (8)
C9—C8—C11—S11.2 (6)C52—C59—C60—C61175.7 (4)
C9—C8—C11—C12179.6 (5)C52—C59—C62—S4175.9 (4)
C9—C10—C13—C142.1 (9)C52—C59—C62—C634.1 (9)
C9—C10—C13—C17176.8 (5)C53—C52—C59—C60130.7 (5)
C10—S1—C11—C80.7 (4)C53—C52—C59—C6250.9 (7)
C10—S1—C11—C12179.2 (5)C53—C54—C55—C563.6 (12)
C10—C13—C14—C15179.2 (6)C54—C53—C58—C570.9 (12)
C10—C13—C17—C16178.5 (5)C54—C55—C56—C571.7 (14)
C11—S1—C10—C90.1 (4)C55—C56—C57—C580.4 (16)
C11—S1—C10—C13178.4 (5)C56—C57—C58—C530.9 (15)
C11—C8—C9—C101.3 (6)C58—C53—C54—C553.1 (11)
C13—C14—C15—N10.5 (11)C59—C52—C53—C5455.0 (8)
C14—C13—C17—C162.6 (8)C59—C52—C53—C58122.1 (7)
C15—N1—C16—C170.4 (10)C59—C60—C61—S41.9 (6)
C16—N1—C15—C140.4 (10)C59—C60—C61—C64177.2 (5)
C17—C13—C14—C152.0 (10)C60—C59—C62—S42.6 (5)
C18—C1—C8—C950.2 (7)C60—C59—C62—C63177.4 (5)
C18—C1—C8—C11129.2 (6)C60—C61—C64—C653.8 (8)
C18—C1—C2—C3129 (2)C60—C61—C64—C68174.3 (5)
C18—C1—C2—C748 (4)C61—S4—C62—C591.4 (4)
C18—C1—C2A—C3A138 (4)C61—S4—C62—C63178.6 (5)
C18—C1—C2A—C7A56 (6)C61—C64—C65—C66176.9 (5)
C18—C19—C20—C21178.9 (5)C61—C64—C68—C67177.1 (5)
C18—C19—C24—C23179.7 (4)C62—S4—C61—C600.2 (4)
C18—C25—C26—C27175.9 (4)C62—S4—C61—C64178.9 (4)
C18—C25—C28—S2177.0 (4)C62—C59—C60—C613.0 (6)
C18—C25—C28—C293.4 (8)C64—C65—C66—N40.6 (9)
C19—C18—C25—C2666.2 (6)C65—C64—C68—C671.1 (7)
C19—C18—C25—C28115.4 (5)C66—N4—C67—C680.9 (8)
C19—C20—C21—C221.6 (8)C67—N4—C66—C650.5 (9)
C20—C19—C24—C230.6 (7)C68—C64—C65—C661.4 (8)
C20—C21—C22—C231.1 (8)O1—C69—C70—C711.6 (7)
C21—C22—C23—C240.3 (8)O1—C69—C70—C75177.6 (5)
C22—C23—C24—C190.0 (8)O2—C69—C70—C71177.9 (5)
C24—C19—C20—C211.4 (8)O2—C69—C70—C752.9 (7)
C25—C18—C19—C2045.0 (6)O3—C71—C72—C73178.9 (5)
C25—C18—C19—C24134.7 (5)C69—C70—C71—O31.4 (7)
C25—C26—C27—S22.4 (5)C69—C70—C71—C72177.8 (5)
C25—C26—C27—C30175.3 (5)C69—C70—C75—O41.6 (8)
C26—C25—C28—S21.5 (5)C69—C70—C75—C74178.4 (5)
C26—C25—C28—C29178.0 (5)C70—C71—C72—C732.0 (8)
C26—C27—C30—C3118.9 (8)C71—C70—C75—O4177.6 (5)
C26—C27—C30—C34160.9 (5)C71—C70—C75—C742.4 (8)
C27—S2—C28—C250.2 (4)C71—C72—C73—C740.1 (9)
C27—S2—C28—C29179.4 (4)C72—C73—C74—C750.5 (10)
C27—C30—C31—C32178.4 (4)C73—C74—C75—O4179.3 (6)
C27—C30—C34—C33179.6 (4)C73—C74—C75—C700.7 (10)
C28—S2—C27—C261.3 (4)C75—C70—C71—O3177.8 (5)
C28—S2—C27—C30176.7 (4)C75—C70—C71—C723.1 (8)
C28—C25—C26—C272.6 (6)O5—C76—C77—C789.4 (8)
C30—C31—C32—N21.4 (7)O5—C76—C77—C82172.2 (5)
C31—C30—C34—C330.3 (7)O6—C76—C77—C78169.8 (5)
C32—N2—C33—C341.4 (7)O6—C76—C77—C828.6 (8)
C33—N2—C32—C310.1 (7)O7—C78—C79—C80177.8 (4)
C34—C30—C31—C321.5 (7)C76—C77—C78—O73.0 (8)
C2—C1—C8—C9128.4 (15)C76—C77—C78—C79176.5 (5)
C2—C1—C8—C1152.2 (16)C76—C77—C82—O82.4 (8)
C2—C1—C18—C195.2 (19)C76—C77—C82—C81177.7 (5)
C2—C1—C18—C25173.3 (17)C77—C78—C79—C802.6 (8)
C2—C3—C4—C62 (3)C78—C77—C82—O8179.1 (5)
C3—C2—C7—C54 (4)C78—C77—C82—C810.8 (8)
C3—C4—C6—C50 (3)C78—C79—C80—C812.2 (8)
C6—C5—C7—C22 (3)C79—C80—C81—C821.2 (8)
C7—C2—C3—C44 (4)C80—C81—C82—O8179.5 (5)
C7—C5—C6—C40 (3)C80—C81—C82—C770.5 (8)
C2A—C1—C8—C9136 (3)C82—C77—C78—O7178.5 (4)
C2A—C1—C8—C1145 (3)C82—C77—C78—C792.0 (8)
C2A—C1—C18—C1913 (3)O9—C83—C84—C852.5 (8)
C2A—C1—C18—C25166 (3)O9—C83—C84—C89177.9 (5)
C2A—C3A—C4A—C5A3 (6)O10—C83—C84—C85177.5 (5)
C3A—C2A—C7A—C6A6 (8)O10—C83—C84—C892.2 (8)
C3A—C4A—C5A—C6A6 (5)O11—C85—C86—C87179.9 (5)
C4A—C5A—C6A—C7A11 (4)C83—C84—C85—O110.7 (8)
C5A—C6A—C7A—C2A5 (5)C83—C84—C85—C86178.6 (5)
C7A—C2A—C3A—C4A9 (8)C83—C84—C89—O120.6 (7)
S3—C44—C47—C48174.6 (4)C83—C84—C89—C88179.1 (5)
S3—C44—C47—C513.9 (7)C84—C85—C86—C870.6 (8)
S4—C61—C64—C65177.2 (4)C85—C84—C89—O12179.7 (5)
S4—C61—C64—C684.7 (7)C85—C84—C89—C880.6 (7)
N3—C50—C51—C470.7 (11)C85—C86—C87—C880.3 (8)
N4—C67—C68—C640.0 (8)C86—C87—C88—C890.7 (8)
C35—C36—C37—C38172.4 (5)C87—C88—C89—O12179.4 (5)
C35—C36—C41—C40173.2 (6)C87—C88—C89—C840.3 (8)
C35—C42—C43—C44177.8 (5)C89—C84—C85—O11179.7 (5)
C35—C42—C45—S3177.4 (4)C89—C84—C85—C861.0 (8)
C35—C42—C45—C460.8 (9)O13—C90—C91—C921.3 (16)
C35—C52—C53—C54123.8 (7)O13—C90—C91—C96178.5 (16)
C35—C52—C53—C5859.1 (9)O14—C90—C91—C92178.4 (16)
C35—C52—C59—C6048.2 (7)O14—C90—C91—C961.8 (17)
C35—C52—C59—C62130.2 (6)O15—C92—C93—C94177.1 (12)
C36—C35—C42—C4366.3 (7)C90—C91—C92—O154 (2)
C36—C35—C42—C45115.6 (6)C90—C91—C92—C93176.3 (13)
C36—C35—C52—C5312.9 (8)C90—C91—C96—O166 (2)
C36—C35—C52—C59165.9 (5)C90—C91—C96—C95179.7 (13)
C36—C37—C38—C391.1 (10)C91—C92—C93—C944 (2)
C37—C36—C41—C400.2 (9)C92—C91—C96—O16174.2 (14)
C37—C38—C39—C400.2 (10)C92—C91—C96—C950 (2)
C38—C39—C40—C410.8 (11)C92—C93—C94—C951 (2)
C39—C40—C41—C361.0 (11)C93—C94—C95—C962 (2)
C41—C36—C37—C380.8 (9)C94—C95—C96—O16176.7 (14)
C42—C35—C36—C3715.8 (7)C94—C95—C96—C913 (2)
C42—C35—C36—C41157.0 (5)C96—C91—C92—O15176.1 (14)
C42—C35—C52—C53167.8 (5)C96—C91—C92—C933 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O15—H15A···O130.84 (2)1.86 (11)2.516 (18)133 (13)
O16—H16A···O140.84 (2)1.68 (5)2.499 (19)162 (14)
N1—H1···N1i0.88 (2)1.76 (3)2.641 (11)174 (19)
N2—H2···O1i0.89 (2)1.79 (2)2.669 (5)172 (7)
N3—H3B···O5i0.88 (2)1.88 (2)2.766 (5)175 (7)
N4—H4B···O9ii0.90 (2)1.71 (3)2.602 (6)170 (8)
O3—H3C···O10.84 (2)1.84 (5)2.561 (5)142 (7)
O4—H4C···O20.84 (2)1.86 (6)2.524 (6)135 (8)
O7—H7B···O50.85 (2)1.75 (3)2.553 (5)158 (8)
O8—H8···O60.84 (2)1.72 (3)2.531 (5)160 (8)
O11—H11···O90.85 (2)1.77 (5)2.515 (6)146 (8)
O12—H12···O100.85 (2)1.77 (4)2.544 (6)149 (8)
Symmetry codes: (i) x, y+1, z+1; (ii) x+1, y+1, z+1.
(dte-5) top
Crystal data top
C34H28N2S2·C10H5O8·C5H2O4F(000) = 1884
Mr = 907.91Dx = 1.336 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.6987 (2) ÅCell parameters from 6590 reflections
b = 20.7245 (5) Åθ = 2.4–23.8°
c = 22.9341 (6) ŵ = 0.18 mm1
β = 101.680 (1)°T = 90 K
V = 4514.32 (19) Å3Prism, green
Z = 40.12 × 0.06 × 0.04 mm
Data collection top
Bruker APEX-II CCD
diffractometer
6215 reflections with I > 2σ(I)
φ and ω scansRint = 0.079
Absorption correction: multi-scan
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1841 before and 0.0535 after correction. The Ratio of minimum to maximum transmission is 0.9548. The λ/2 correction factor is Not present.
θmax = 26.4°, θmin = 1.3°
Tmin = 0.712, Tmax = 0.745h = 1012
57175 measured reflectionsk = 2525
9238 independent reflectionsl = 2828
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.052H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.118 w = 1/[σ2(Fo2) + (0.0438P)2 + 2.8563P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
9238 reflectionsΔρmax = 0.46 e Å3
631 parametersΔρmin = 0.40 e Å3
5 restraints
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)
S10.14749 (8)0.28773 (3)0.28157 (3)0.03515 (19)
S20.40518 (9)0.32119 (3)0.27207 (3)0.03811 (19)
N10.1231 (2)0.13683 (10)0.45741 (10)0.0223 (5)
N20.8210 (2)0.28595 (11)0.46054 (11)0.0347 (6)
C10.0398 (3)0.46154 (13)0.29057 (11)0.0294 (6)
C20.0724 (3)0.51135 (14)0.27680 (12)0.0338 (7)
C30.1743 (3)0.51771 (17)0.31114 (15)0.0539 (10)
H30.1682590.4921080.3459240.065*
C40.2845 (4)0.5609 (2)0.29533 (19)0.0824 (15)
H40.3539960.5649620.3189610.099*
C50.2921 (4)0.5982 (2)0.24460 (18)0.0771 (14)
H50.3679890.6275480.2331840.093*
C60.1912 (3)0.59310 (16)0.21069 (15)0.0487 (9)
H60.1970970.6190750.1761460.058*
C70.0810 (3)0.55025 (13)0.22674 (12)0.0339 (7)
H70.0105750.5473080.2034520.041*
C80.0093 (3)0.39422 (13)0.29653 (12)0.0313 (6)
C90.0622 (3)0.35015 (12)0.33978 (11)0.0244 (6)
H90.1448770.3614040.3678610.029*
C100.0022 (2)0.29007 (12)0.33766 (11)0.0227 (5)
C110.1273 (3)0.36677 (14)0.26204 (12)0.0375 (7)
C120.2322 (4)0.39429 (17)0.21049 (14)0.0586 (11)
H12A0.2857930.3590790.1879950.088*
H12B0.1821810.4183850.1843810.088*
H12C0.2967190.4232860.2255610.088*
C130.0463 (2)0.23530 (11)0.37674 (11)0.0203 (5)
C140.1695 (2)0.23865 (12)0.42021 (12)0.0257 (6)
H140.2286970.2754320.4221690.031*
C150.2057 (2)0.18948 (12)0.45998 (12)0.0264 (6)
H150.2894500.1923980.4896110.032*
C160.0069 (2)0.13015 (12)0.41458 (11)0.0226 (6)
H160.0479810.0919490.4126040.027*
C170.0326 (3)0.17850 (12)0.37371 (11)0.0227 (5)
H170.1140050.1733170.3431490.027*
C180.1781 (3)0.47647 (12)0.29621 (11)0.0246 (6)
C190.2292 (2)0.54439 (12)0.30492 (11)0.0235 (6)
C200.3195 (3)0.57024 (12)0.27074 (12)0.0267 (6)
H200.3504350.5442550.2417600.032*
C210.3641 (3)0.63368 (13)0.27893 (13)0.0338 (7)
H210.4227740.6514450.2545000.041*
C220.3240 (3)0.67132 (13)0.32231 (13)0.0359 (7)
H220.3568790.7144730.3283290.043*
C230.2366 (3)0.64622 (14)0.35670 (13)0.0362 (7)
H230.2090440.6719810.3866510.043*
C240.1884 (3)0.58343 (13)0.34779 (12)0.0305 (6)
H240.1265250.5667190.3713200.037*
C250.2857 (3)0.42554 (12)0.29630 (11)0.0269 (6)
C260.4077 (3)0.41702 (12)0.34235 (12)0.0257 (6)
H260.4356890.4469310.3739140.031*
C270.4804 (3)0.36154 (12)0.33657 (12)0.0268 (6)
C280.2741 (3)0.37826 (13)0.25334 (12)0.0331 (7)
C290.1682 (4)0.37222 (16)0.19656 (13)0.0495 (9)
H29A0.2147910.3571910.1649320.074*
H29B0.1246430.4143410.1856430.074*
H29C0.0954990.3411460.2018170.074*
C300.6010 (3)0.33471 (12)0.37813 (12)0.0278 (6)
C310.7110 (3)0.37435 (12)0.40597 (13)0.0313 (7)
H310.7099330.4190350.3966510.038*
C320.8206 (3)0.34897 (13)0.44674 (13)0.0342 (7)
H320.8962270.3758910.4652110.041*
C330.7178 (3)0.24573 (13)0.43437 (13)0.0326 (7)
H330.7212740.2013700.4450090.039*
C340.6086 (3)0.26863 (12)0.39270 (13)0.0292 (6)
H340.5373750.2399720.3733840.035*
O10.15288 (15)0.44436 (7)0.05522 (7)0.0184 (4)
O20.21095 (15)0.51778 (7)0.12654 (7)0.0181 (4)
O30.50248 (16)0.28625 (8)0.04513 (8)0.0259 (4)
O40.73232 (16)0.30715 (8)0.07405 (8)0.0268 (4)
O50.90758 (15)0.45893 (8)0.08324 (8)0.0234 (4)
O60.81109 (16)0.40799 (8)0.00158 (8)0.0224 (4)
O70.38082 (16)0.60843 (7)0.13183 (7)0.0190 (4)
O80.55012 (16)0.63336 (7)0.08472 (8)0.0238 (4)
C350.3937 (2)0.47203 (10)0.08302 (10)0.0132 (5)
C360.4346 (2)0.40920 (11)0.07359 (10)0.0149 (5)
H360.3683790.3753420.0730800.018*
C370.5685 (2)0.39396 (10)0.06489 (10)0.0132 (5)
C380.6634 (2)0.44423 (10)0.06299 (10)0.0136 (5)
C390.6253 (2)0.50668 (10)0.07430 (10)0.0133 (5)
H390.6916800.5403770.0743050.016*
C400.4927 (2)0.52210 (10)0.08573 (10)0.0138 (5)
C410.2416 (2)0.47977 (10)0.08863 (10)0.0143 (5)
C420.6097 (2)0.32426 (11)0.06106 (10)0.0181 (5)
C430.8022 (2)0.43356 (10)0.04492 (10)0.0139 (5)
C440.4741 (2)0.59280 (11)0.09972 (10)0.0160 (5)
O90.45208 (18)0.67173 (8)0.47900 (8)0.0289 (4)
C450.5525 (3)0.63535 (12)0.47802 (14)0.0323 (7)
C460.5325 (2)0.56472 (11)0.48966 (11)0.0169 (5)
C470.3945 (2)0.54433 (11)0.48699 (10)0.0161 (5)
H470.3210710.5752830.4777910.019*
C480.3590 (2)0.48103 (10)0.49711 (10)0.0160 (5)
C490.2032 (2)0.46755 (12)0.49153 (11)0.0223 (6)
O100.6569 (9)0.6481 (4)0.4515 (5)0.092 (4)0.517 (6)
H100.7288440.6280590.4688700.111*0.517 (6)
O110.1491 (3)0.49767 (18)0.5307 (2)0.0320 (15)0.517 (6)
O120.1480 (7)0.4251 (4)0.4603 (4)0.077 (3)0.517 (6)
O10A0.6684 (7)0.6620 (4)0.4854 (4)0.050 (2)0.483 (6)
H10.143 (3)0.1077 (13)0.4871 (11)0.060*
H20.894 (3)0.2701 (15)0.4915 (12)0.060*
H3A0.524 (3)0.2459 (10)0.0390 (14)0.060*
H5A0.985 (2)0.4531 (16)0.0717 (14)0.060*
H7A0.326 (3)0.5760 (12)0.1344 (14)0.060*
O11A0.1230 (3)0.51944 (16)0.4805 (2)0.0268 (15)0.483 (6)
H11A0.0383730.5086930.4776920.032*0.483 (6)
O12A0.1465 (5)0.4153 (2)0.4920 (3)0.0298 (15)0.483 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0413 (4)0.0342 (4)0.0249 (4)0.0183 (3)0.0053 (3)0.0063 (3)
S20.0598 (5)0.0218 (4)0.0366 (4)0.0038 (3)0.0190 (4)0.0062 (3)
N10.0177 (10)0.0158 (11)0.0360 (13)0.0020 (8)0.0115 (10)0.0038 (9)
N20.0327 (13)0.0291 (14)0.0467 (16)0.0077 (11)0.0189 (11)0.0064 (12)
C10.0358 (15)0.0289 (15)0.0211 (14)0.0080 (12)0.0003 (12)0.0090 (12)
C20.0262 (14)0.0385 (17)0.0334 (16)0.0078 (12)0.0016 (12)0.0155 (13)
C30.0358 (17)0.072 (2)0.057 (2)0.0049 (16)0.0161 (16)0.0405 (19)
C40.043 (2)0.123 (4)0.091 (3)0.029 (2)0.036 (2)0.068 (3)
C50.0360 (19)0.107 (3)0.093 (3)0.029 (2)0.024 (2)0.066 (3)
C60.0257 (15)0.066 (2)0.053 (2)0.0020 (15)0.0043 (14)0.0357 (18)
C70.0256 (14)0.0378 (17)0.0352 (16)0.0088 (12)0.0012 (12)0.0149 (13)
C80.0329 (14)0.0335 (16)0.0248 (14)0.0120 (12)0.0004 (12)0.0080 (12)
C90.0260 (13)0.0264 (14)0.0196 (13)0.0065 (11)0.0017 (11)0.0026 (11)
C100.0244 (13)0.0242 (14)0.0191 (13)0.0071 (11)0.0037 (10)0.0011 (11)
C110.0459 (17)0.0363 (17)0.0253 (15)0.0151 (14)0.0044 (13)0.0152 (13)
C120.061 (2)0.061 (2)0.0391 (19)0.0274 (18)0.0242 (17)0.0276 (17)
C130.0209 (12)0.0206 (13)0.0218 (13)0.0019 (10)0.0097 (10)0.0014 (11)
C140.0193 (12)0.0195 (13)0.0389 (16)0.0055 (10)0.0070 (11)0.0032 (12)
C150.0157 (12)0.0222 (14)0.0413 (16)0.0012 (10)0.0054 (11)0.0051 (12)
C160.0204 (13)0.0192 (13)0.0318 (15)0.0025 (10)0.0140 (11)0.0050 (11)
C170.0226 (12)0.0222 (14)0.0247 (13)0.0053 (10)0.0081 (11)0.0037 (11)
C180.0330 (14)0.0220 (14)0.0180 (13)0.0056 (11)0.0034 (11)0.0049 (11)
C190.0222 (12)0.0220 (14)0.0228 (14)0.0011 (10)0.0035 (11)0.0035 (11)
C200.0272 (13)0.0223 (14)0.0298 (15)0.0014 (11)0.0037 (12)0.0012 (11)
C210.0297 (14)0.0241 (15)0.0458 (18)0.0036 (12)0.0035 (13)0.0056 (13)
C220.0392 (16)0.0189 (14)0.0424 (18)0.0008 (12)0.0085 (14)0.0020 (13)
C230.0459 (17)0.0288 (16)0.0311 (16)0.0055 (13)0.0011 (14)0.0035 (13)
C240.0329 (15)0.0303 (16)0.0276 (15)0.0028 (12)0.0046 (12)0.0036 (12)
C250.0381 (15)0.0185 (14)0.0264 (15)0.0077 (11)0.0123 (12)0.0037 (11)
C260.0335 (14)0.0161 (13)0.0308 (15)0.0054 (11)0.0142 (12)0.0002 (11)
C270.0359 (15)0.0157 (13)0.0329 (15)0.0068 (11)0.0166 (12)0.0003 (11)
C280.0517 (18)0.0237 (15)0.0267 (15)0.0076 (13)0.0148 (13)0.0009 (12)
C290.078 (2)0.0433 (19)0.0258 (16)0.0093 (17)0.0067 (16)0.0002 (14)
C300.0322 (14)0.0189 (13)0.0395 (16)0.0007 (11)0.0242 (13)0.0028 (12)
C310.0354 (15)0.0170 (14)0.0495 (18)0.0029 (12)0.0274 (14)0.0035 (13)
C320.0304 (15)0.0235 (15)0.0547 (19)0.0036 (12)0.0225 (14)0.0124 (14)
C330.0356 (15)0.0182 (14)0.0498 (18)0.0004 (12)0.0226 (14)0.0016 (13)
C340.0329 (15)0.0162 (13)0.0439 (17)0.0026 (11)0.0206 (13)0.0046 (12)
O10.0083 (7)0.0158 (9)0.0315 (10)0.0015 (6)0.0049 (7)0.0051 (7)
O20.0138 (8)0.0151 (9)0.0269 (9)0.0012 (7)0.0078 (7)0.0035 (7)
O30.0139 (8)0.0087 (8)0.0538 (12)0.0008 (7)0.0041 (8)0.0041 (8)
O40.0118 (8)0.0164 (9)0.0523 (12)0.0046 (7)0.0066 (8)0.0033 (8)
O50.0079 (8)0.0319 (10)0.0310 (10)0.0019 (7)0.0058 (7)0.0091 (8)
O60.0160 (8)0.0237 (9)0.0297 (10)0.0014 (7)0.0097 (7)0.0061 (8)
O70.0157 (8)0.0123 (8)0.0310 (10)0.0004 (6)0.0092 (7)0.0048 (7)
O80.0226 (9)0.0114 (9)0.0399 (11)0.0025 (7)0.0123 (8)0.0005 (8)
C350.0093 (10)0.0124 (12)0.0178 (12)0.0005 (9)0.0025 (9)0.0015 (9)
C360.0122 (11)0.0105 (12)0.0220 (13)0.0025 (9)0.0034 (10)0.0013 (10)
C370.0104 (10)0.0116 (11)0.0172 (12)0.0013 (9)0.0016 (9)0.0008 (9)
C380.0107 (10)0.0133 (12)0.0159 (12)0.0004 (9)0.0007 (9)0.0002 (10)
C390.0101 (10)0.0113 (11)0.0180 (12)0.0030 (9)0.0012 (9)0.0003 (9)
C400.0122 (10)0.0110 (11)0.0177 (12)0.0017 (9)0.0013 (9)0.0007 (9)
C410.0118 (10)0.0076 (11)0.0239 (13)0.0016 (9)0.0042 (10)0.0032 (10)
C420.0163 (12)0.0139 (12)0.0253 (13)0.0003 (10)0.0070 (10)0.0015 (10)
C430.0106 (11)0.0087 (11)0.0228 (13)0.0002 (9)0.0039 (10)0.0019 (10)
C440.0118 (11)0.0140 (12)0.0213 (13)0.0017 (9)0.0014 (10)0.0002 (10)
O90.0304 (10)0.0128 (9)0.0475 (12)0.0068 (8)0.0173 (9)0.0034 (8)
C450.0226 (14)0.0143 (13)0.0575 (19)0.0016 (11)0.0020 (13)0.0064 (13)
C460.0156 (11)0.0103 (11)0.0272 (14)0.0002 (9)0.0102 (10)0.0004 (10)
C470.0132 (11)0.0114 (12)0.0246 (13)0.0031 (9)0.0060 (10)0.0020 (10)
C480.0122 (10)0.0109 (12)0.0266 (13)0.0009 (9)0.0079 (10)0.0035 (10)
C490.0173 (12)0.0208 (14)0.0306 (15)0.0055 (11)0.0091 (11)0.0069 (12)
O100.069 (5)0.026 (4)0.218 (11)0.018 (3)0.112 (7)0.044 (5)
O110.0183 (18)0.030 (2)0.052 (3)0.0083 (15)0.0172 (18)0.020 (2)
O120.040 (3)0.106 (6)0.096 (6)0.050 (3)0.042 (4)0.080 (5)
O10A0.011 (2)0.018 (3)0.117 (6)0.007 (2)0.001 (3)0.005 (3)
O11A0.0072 (16)0.012 (2)0.063 (4)0.0017 (14)0.0115 (18)0.0024 (19)
O12A0.010 (2)0.007 (2)0.072 (4)0.0014 (15)0.009 (3)0.007 (3)
Geometric parameters (Å, º) top
S1—C101.735 (2)C25—C281.378 (4)
S1—C111.720 (3)C26—H260.9500
S2—C271.727 (3)C26—C271.369 (3)
S2—C281.725 (3)C27—C301.460 (4)
N1—C151.347 (3)C28—C291.492 (4)
N1—C161.344 (3)C29—H29A0.9800
N1—H10.902 (18)C29—H29B0.9800
N2—C321.344 (3)C29—H29C0.9800
N2—C331.347 (3)C30—C311.395 (4)
N2—H20.953 (18)C30—C341.408 (3)
C1—C21.486 (4)C31—H310.9500
C1—C81.489 (4)C31—C321.371 (4)
C1—C181.357 (4)C32—H320.9500
C2—C31.389 (4)C33—H330.9500
C2—C71.391 (4)C33—C341.360 (4)
C3—H30.9500C34—H340.9500
C3—C41.386 (5)O1—C411.265 (3)
C4—H40.9500O2—C411.253 (3)
C4—C51.386 (5)O3—C421.297 (3)
C5—H50.9500O3—H3A0.880 (18)
C5—C61.372 (5)O4—C421.219 (3)
C6—H60.9500O5—C431.315 (3)
C6—C71.381 (4)O5—H5A0.854 (18)
C7—H70.9500O6—C431.209 (3)
C8—C91.421 (3)O7—C441.317 (3)
C8—C111.376 (4)O7—H7A0.867 (18)
C9—H90.9500O8—C441.213 (3)
C9—C101.371 (3)C35—C361.391 (3)
C10—C131.456 (3)C35—C401.407 (3)
C11—C121.507 (4)C35—C411.516 (3)
C12—H12A0.9800C36—H360.9500
C12—H12B0.9800C36—C371.389 (3)
C12—H12C0.9800C37—C381.397 (3)
C13—C141.394 (3)C37—C421.506 (3)
C13—C171.398 (3)C38—C391.385 (3)
C14—H140.9500C38—C431.503 (3)
C14—C151.365 (3)C39—H390.9500
C15—H150.9500C39—C401.400 (3)
C16—H160.9500C40—C441.519 (3)
C16—C171.372 (3)O9—C451.236 (3)
C17—H170.9500C45—C461.507 (3)
C18—C191.492 (3)C45—O101.310 (7)
C18—C251.484 (4)C45—O10A1.233 (7)
C19—C201.395 (4)C46—C471.393 (3)
C19—C241.391 (4)C46—C48i1.403 (3)
C20—H200.9500C47—H470.9500
C20—C211.385 (4)C47—C481.388 (3)
C21—H210.9500C48—C491.517 (3)
C21—C221.380 (4)C49—O111.289 (4)
C22—H220.9500C49—O121.190 (6)
C22—C231.372 (4)C49—O11A1.321 (4)
C23—H230.9500C49—O12A1.215 (6)
C23—C241.384 (4)O10—H100.8402
C24—H240.9500O11A—H11A0.8400
C25—C261.428 (4)
C11—S1—C1092.52 (12)C25—C26—H26123.3
C28—S2—C2792.51 (13)C27—C26—C25113.5 (2)
C15—N1—H1118 (2)C27—C26—H26123.3
C16—N1—C15121.2 (2)C26—C27—S2110.7 (2)
C16—N1—H1120 (2)C26—C27—C30128.1 (2)
C32—N2—C33122.1 (3)C30—C27—S2121.22 (19)
C32—N2—H2118 (2)C25—C28—S2111.1 (2)
C33—N2—H2119 (2)C25—C28—C29128.7 (3)
C2—C1—C8115.9 (2)C29—C28—S2120.1 (2)
C18—C1—C2121.9 (2)C28—C29—H29A109.5
C18—C1—C8122.2 (2)C28—C29—H29B109.5
C3—C2—C1121.3 (2)C28—C29—H29C109.5
C3—C2—C7118.8 (3)H29A—C29—H29B109.5
C7—C2—C1119.8 (3)H29A—C29—H29C109.5
C2—C3—H3119.6H29B—C29—H29C109.5
C4—C3—C2120.9 (3)C31—C30—C27120.8 (2)
C4—C3—H3119.6C31—C30—C34117.7 (2)
C3—C4—H4120.4C34—C30—C27121.5 (2)
C3—C4—C5119.1 (3)C30—C31—H31119.9
C5—C4—H4120.4C32—C31—C30120.1 (2)
C4—C5—H5119.7C32—C31—H31119.9
C6—C5—C4120.7 (3)N2—C32—C31119.9 (3)
C6—C5—H5119.7N2—C32—H32120.1
C5—C6—H6120.0C31—C32—H32120.1
C5—C6—C7120.1 (3)N2—C33—H33120.0
C7—C6—H6120.0N2—C33—C34120.0 (2)
C2—C7—H7119.8C34—C33—H33120.0
C6—C7—C2120.4 (3)C30—C34—H34119.9
C6—C7—H7119.8C33—C34—C30120.2 (3)
C9—C8—C1123.1 (2)C33—C34—H34119.9
C11—C8—C1125.4 (2)C42—O3—H3A115 (2)
C11—C8—C9111.5 (2)C43—O5—H5A110 (2)
C8—C9—H9122.7C44—O7—H7A110 (2)
C10—C9—C8114.5 (2)C36—C35—C40118.93 (19)
C10—C9—H9122.7C36—C35—C41115.20 (18)
C9—C10—S1109.72 (18)C40—C35—C41125.86 (19)
C9—C10—C13128.1 (2)C35—C36—H36118.7
C13—C10—S1122.15 (18)C37—C36—C35122.7 (2)
C8—C11—S1111.7 (2)C37—C36—H36118.7
C8—C11—C12130.2 (3)C36—C37—C38118.4 (2)
C12—C11—S1118.1 (2)C36—C37—C42119.55 (19)
C11—C12—H12A109.5C38—C37—C42121.95 (19)
C11—C12—H12B109.5C37—C38—C43122.12 (19)
C11—C12—H12C109.5C39—C38—C37119.25 (19)
H12A—C12—H12B109.5C39—C38—C43118.49 (19)
H12A—C12—H12C109.5C38—C39—H39118.7
H12B—C12—H12C109.5C38—C39—C40122.6 (2)
C14—C13—C10120.2 (2)C40—C39—H39118.7
C14—C13—C17117.3 (2)C35—C40—C44127.71 (19)
C17—C13—C10122.4 (2)C39—C40—C35117.89 (19)
C13—C14—H14119.8C39—C40—C44114.39 (19)
C15—C14—C13120.5 (2)O1—C41—C35116.21 (19)
C15—C14—H14119.8O2—C41—O1123.90 (19)
N1—C15—C14120.4 (2)O2—C41—C35119.82 (19)
N1—C15—H15119.8O3—C42—C37113.07 (18)
C14—C15—H15119.8O4—C42—O3125.4 (2)
N1—C16—H16120.0O4—C42—C37121.5 (2)
N1—C16—C17120.0 (2)O5—C43—C38112.03 (19)
C17—C16—H16120.0O6—C43—O5125.5 (2)
C13—C17—H17119.8O6—C43—C38122.35 (19)
C16—C17—C13120.4 (2)O7—C44—C40118.68 (19)
C16—C17—H17119.8O8—C44—O7120.9 (2)
C1—C18—C19121.5 (2)O8—C44—C40120.2 (2)
C1—C18—C25121.3 (2)O9—C45—C46117.3 (2)
C25—C18—C19117.1 (2)O9—C45—O10124.9 (4)
C20—C19—C18121.1 (2)O10—C45—C46114.7 (4)
C24—C19—C18120.6 (2)O10A—C45—O9115.2 (4)
C24—C19—C20118.3 (2)O10A—C45—C46123.8 (4)
C19—C20—H20119.9C47—C46—C45116.3 (2)
C21—C20—C19120.2 (3)C47—C46—C48i118.4 (2)
C21—C20—H20119.9C48i—C46—C45125.2 (2)
C20—C21—H21119.7C46—C47—H47118.4
C22—C21—C20120.6 (3)C48—C47—C46123.2 (2)
C22—C21—H21119.7C48—C47—H47118.4
C21—C22—H22120.1C46i—C48—C49125.8 (2)
C23—C22—C21119.8 (3)C47—C48—C46i118.34 (19)
C23—C22—H22120.1C47—C48—C49115.89 (19)
C22—C23—H23120.0O11—C49—C48113.0 (2)
C22—C23—C24120.1 (3)O12—C49—C48120.4 (4)
C24—C23—H23120.0O12—C49—O11125.5 (4)
C19—C24—H24119.5O11A—C49—C48113.8 (2)
C23—C24—C19121.0 (3)O12A—C49—C48127.5 (3)
C23—C24—H24119.5O12A—C49—O11A118.5 (3)
C26—C25—C18124.5 (2)C45—O10—H10108.9
C28—C25—C18123.3 (2)C49—O11A—H11A109.1
C28—C25—C26112.1 (2)
S1—C10—C13—C14178.23 (19)C25—C26—C27—C30173.7 (2)
S1—C10—C13—C173.3 (3)C26—C25—C28—S24.0 (3)
S2—C27—C30—C31140.1 (2)C26—C25—C28—C29175.7 (3)
S2—C27—C30—C3441.6 (3)C26—C27—C30—C3143.2 (4)
N1—C16—C17—C130.9 (4)C26—C27—C30—C34135.1 (3)
N2—C33—C34—C301.9 (4)C27—S2—C28—C251.8 (2)
C1—C2—C3—C4175.0 (3)C27—S2—C28—C29177.9 (2)
C1—C2—C7—C6174.7 (3)C27—C30—C31—C32177.3 (2)
C1—C8—C9—C10179.0 (3)C27—C30—C34—C33175.8 (2)
C1—C8—C11—S1179.0 (2)C28—S2—C27—C260.9 (2)
C1—C8—C11—C121.8 (6)C28—S2—C27—C30176.3 (2)
C1—C18—C19—C20131.6 (3)C28—C25—C26—C274.8 (3)
C1—C18—C19—C2448.8 (3)C30—C31—C32—N21.0 (4)
C1—C18—C25—C26124.9 (3)C31—C30—C34—C332.5 (4)
C1—C18—C25—C2850.8 (4)C32—N2—C33—C340.2 (4)
C2—C1—C8—C9141.4 (3)C33—N2—C32—C311.7 (4)
C2—C1—C8—C1138.4 (4)C34—C30—C31—C321.1 (4)
C2—C1—C18—C1916.4 (4)C35—C36—C37—C382.9 (3)
C2—C1—C18—C25166.0 (2)C35—C36—C37—C42173.9 (2)
C2—C3—C4—C50.2 (7)C35—C40—C44—O725.3 (3)
C3—C2—C7—C61.8 (4)C35—C40—C44—O8159.3 (2)
C3—C4—C5—C60.8 (7)C36—C35—C40—C394.7 (3)
C4—C5—C6—C70.4 (6)C36—C35—C40—C44175.5 (2)
C5—C6—C7—C20.9 (5)C36—C35—C41—O137.4 (3)
C7—C2—C3—C41.4 (5)C36—C35—C41—O2139.9 (2)
C8—C1—C2—C352.6 (4)C36—C37—C38—C394.9 (3)
C8—C1—C2—C7123.8 (3)C36—C37—C38—C43170.8 (2)
C8—C1—C18—C19164.9 (2)C36—C37—C42—O323.5 (3)
C8—C1—C18—C2512.7 (4)C36—C37—C42—O4154.1 (2)
C8—C9—C10—S10.7 (3)C37—C38—C39—C402.2 (3)
C8—C9—C10—C13177.6 (2)C37—C38—C43—O5130.1 (2)
C9—C8—C11—S11.2 (3)C37—C38—C43—O654.2 (3)
C9—C8—C11—C12178.4 (3)C38—C37—C42—O3159.9 (2)
C9—C10—C13—C145.2 (4)C38—C37—C42—O422.5 (3)
C9—C10—C13—C17173.2 (2)C38—C39—C40—C352.7 (3)
C10—S1—C11—C80.7 (2)C38—C39—C40—C44177.5 (2)
C10—S1—C11—C12178.3 (3)C39—C38—C43—O554.1 (3)
C10—C13—C14—C15174.9 (2)C39—C38—C43—O6121.6 (2)
C10—C13—C17—C16174.6 (2)C39—C40—C44—O7154.8 (2)
C11—S1—C10—C90.0 (2)C39—C40—C44—O820.5 (3)
C11—S1—C10—C13177.1 (2)C40—C35—C36—C372.0 (3)
C11—C8—C9—C101.3 (4)C40—C35—C41—O1141.7 (2)
C13—C14—C15—N10.5 (4)C40—C35—C41—O241.0 (3)
C14—C13—C17—C163.9 (3)C41—C35—C36—C37177.1 (2)
C15—N1—C16—C172.4 (3)C41—C35—C40—C39174.4 (2)
C16—N1—C15—C142.6 (4)C41—C35—C40—C445.5 (4)
C17—C13—C14—C153.6 (4)C42—C37—C38—C39171.8 (2)
C18—C1—C2—C3128.6 (3)C42—C37—C38—C4312.5 (3)
C18—C1—C2—C755.0 (4)C43—C38—C39—C40173.7 (2)
C18—C1—C8—C939.8 (4)O9—C45—C46—C4714.2 (4)
C18—C1—C8—C11140.4 (3)O9—C45—C46—C48i165.6 (2)
C18—C19—C20—C21179.1 (2)C45—C46—C47—C48179.5 (2)
C18—C19—C24—C23179.2 (2)C46—C47—C48—C46i0.4 (4)
C18—C25—C26—C27171.3 (2)C46—C47—C48—C49179.3 (2)
C18—C25—C28—S2172.17 (19)C46i—C48—C49—O11117.2 (3)
C18—C25—C28—C298.2 (4)C46i—C48—C49—O1251.2 (7)
C19—C18—C25—C2652.8 (3)C46i—C48—C49—O11A178.1 (3)
C19—C18—C25—C28131.5 (3)C46i—C48—C49—O12A7.4 (6)
C19—C20—C21—C222.3 (4)C47—C48—C49—O1164.0 (4)
C20—C19—C24—C230.4 (4)C47—C48—C49—O12127.6 (6)
C20—C21—C22—C231.5 (4)C47—C48—C49—O11A3.1 (4)
C21—C22—C23—C240.2 (4)C47—C48—C49—O12A171.4 (5)
C22—C23—C24—C191.2 (4)C48i—C46—C47—C480.4 (4)
C24—C19—C20—C211.3 (4)O10—C45—C46—C47146.9 (6)
C25—C18—C19—C2050.7 (3)O10—C45—C46—C48i33.3 (7)
C25—C18—C19—C24128.9 (3)O10A—C45—C46—C47171.4 (5)
C25—C26—C27—S23.3 (3)O10A—C45—C46—C48i8.4 (6)
Symmetry code: (i) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1ii0.90 (2)1.88 (2)2.772 (3)168 (3)
O3—H3A···O9iii0.88 (2)1.62 (2)2.496 (2)173 (3)
O5—H5A···O1iv0.85 (2)1.75 (2)2.605 (2)174 (3)
O7—H7A···O20.87 (2)1.63 (2)2.485 (2)170 (3)
O11A—H11A···O11Av0.842.082.829 (7)149
Symmetry codes: (ii) x, y+1/2, z+1/2; (iii) x+1, y1/2, z+1/2; (iv) x+1, y, z; (v) x, y+1, z+1.
(dte-6) top
Crystal data top
C34H26N2S2·C8H6O4Dx = 1.278 Mg m3
Mr = 692.81Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna21Cell parameters from 9888 reflections
a = 30.6739 (12) Åθ = 2.2–28.7°
b = 9.6686 (4) ŵ = 0.19 mm1
c = 24.2850 (9) ÅT = 90 K
V = 7202.3 (5) Å3Plate, colourless
Z = 80.2 × 0.16 × 0.02 mm
F(000) = 2896
Data collection top
Bruker APEX-II CCD
diffractometer
19739 reflections with I > 2σ(I)
φ and ω scansRint = 0.057
Absorption correction: multi-scan
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1275 before and 0.0556 after correction. The Ratio of minimum to maximum transmission is 0.9397. The λ/2 correction factor is Not present.
θmax = 30.5°, θmin = 1.3°
Tmin = 0.702, Tmax = 0.747h = 4343
162249 measured reflectionsk = 1313
21979 independent reflectionsl = 3434
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.036 w = 1/[σ2(Fo2) + (0.0444P)2 + 1.5553P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.088(Δ/σ)max = 0.004
S = 1.03Δρmax = 0.28 e Å3
21979 reflectionsΔρmin = 0.21 e Å3
919 parametersAbsolute structure: Refined as an inversion twin.
5 restraintsAbsolute structure parameter: 0.41 (4)
Primary atom site location: dual
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.

Refinement. Refined as a 2-component inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.83546 (2)0.12898 (6)0.73324 (2)0.01645 (11)
S20.88049 (2)0.09181 (6)0.53158 (2)0.01615 (10)
N10.89436 (7)0.3992 (2)0.70858 (9)0.0205 (4)
N20.89620 (7)0.4314 (2)0.45988 (9)0.0224 (4)
C10.74856 (7)0.2014 (2)0.61275 (9)0.0139 (4)
C20.70838 (7)0.2560 (2)0.63986 (9)0.0134 (4)
C30.69028 (8)0.1811 (2)0.68334 (9)0.0180 (4)
H30.7016490.0924560.6922650.022*
C40.65584 (8)0.2346 (3)0.71369 (10)0.0207 (5)
H40.6435710.1823800.7429920.025*
C50.63937 (7)0.3645 (2)0.70111 (10)0.0194 (4)
H50.6163800.4024560.7225210.023*
C60.65641 (7)0.4389 (2)0.65740 (10)0.0178 (4)
H60.6446900.5270460.6485060.021*
C70.69066 (7)0.3851 (2)0.62638 (9)0.0145 (4)
H70.7019810.4359450.5961150.017*
C80.78221 (7)0.1529 (2)0.65244 (9)0.0137 (4)
C90.79984 (7)0.0171 (2)0.64983 (9)0.0142 (4)
H90.7919420.0478020.6222040.017*
C100.82905 (7)0.0118 (2)0.69044 (9)0.0137 (4)
C110.79880 (7)0.2270 (2)0.69593 (9)0.0154 (4)
C120.79042 (8)0.3749 (2)0.71163 (10)0.0212 (5)
H12A0.8170340.4151300.7271640.032*
H12B0.7817240.4273230.6788950.032*
H12C0.7670290.3786100.7390770.032*
C130.85187 (7)0.1432 (2)0.69785 (9)0.0140 (4)
C140.85974 (7)0.2282 (2)0.65203 (10)0.0166 (4)
H140.8505970.2004870.6163240.020*
C150.88097 (8)0.3527 (2)0.65964 (11)0.0195 (5)
H150.8863680.4086080.6282000.023*
C160.88689 (8)0.3180 (2)0.75240 (10)0.0213 (5)
H160.8963270.3493550.7875130.026*
C170.86603 (8)0.1904 (2)0.74914 (9)0.0193 (4)
H170.8615070.1363640.7812980.023*
C180.75515 (7)0.1856 (2)0.55781 (9)0.0132 (4)
C190.72139 (7)0.2005 (2)0.51420 (9)0.0151 (4)
C200.73326 (8)0.2527 (2)0.46235 (10)0.0197 (4)
H200.7620270.2860620.4565990.024*
C210.70344 (9)0.2559 (3)0.41944 (10)0.0245 (5)
H210.7117010.2927350.3847060.029*
C220.66141 (9)0.2053 (3)0.42723 (11)0.0243 (5)
H220.6411240.2059490.3976700.029*
C230.64927 (8)0.1540 (3)0.47821 (11)0.0219 (5)
H230.6204520.1207040.4836320.026*
C240.67893 (7)0.1509 (2)0.52159 (10)0.0175 (4)
H240.6703130.1149020.5563300.021*
C250.79829 (7)0.1348 (2)0.53866 (9)0.0136 (4)
C260.80351 (7)0.0011 (2)0.51391 (9)0.0143 (4)
H260.7797140.0544480.5022050.017*
C270.84620 (7)0.0384 (2)0.50882 (9)0.0141 (4)
C280.83755 (7)0.1977 (2)0.54898 (9)0.0153 (4)
C290.84646 (8)0.3373 (2)0.57329 (10)0.0203 (5)
H29A0.8646570.3910210.5479290.030*
H29B0.8188290.3859230.5793570.030*
H29C0.8617040.3264120.6084850.030*
C300.86357 (7)0.1716 (2)0.49092 (9)0.0154 (4)
C310.83840 (8)0.2637 (2)0.46019 (10)0.0194 (4)
H310.8096510.2394890.4493000.023*
C320.85582 (8)0.3913 (2)0.44569 (11)0.0223 (5)
H320.8383350.4530900.4247560.027*
C330.92042 (8)0.3429 (3)0.48855 (11)0.0214 (5)
H330.9491820.3698180.4983590.026*
C340.90591 (8)0.2136 (2)0.50486 (10)0.0186 (4)
H340.9244660.1538930.5252760.022*
S30.56331 (2)0.62644 (5)0.31552 (2)0.01425 (10)
S40.52677 (2)0.58191 (5)0.51548 (2)0.01467 (10)
N30.50211 (7)0.1021 (2)0.34052 (9)0.0206 (4)
N40.51279 (7)0.0590 (2)0.58866 (9)0.0195 (4)
C350.65751 (7)0.6888 (2)0.42825 (9)0.0124 (4)
C360.69795 (7)0.7413 (2)0.40124 (9)0.0131 (4)
C370.71845 (8)0.6586 (2)0.36153 (10)0.0186 (4)
H370.7076330.5683640.3541640.022*
C380.75448 (8)0.7076 (3)0.33286 (10)0.0215 (5)
H380.7687180.6499720.3067760.026*
C390.76965 (7)0.8404 (3)0.34225 (10)0.0205 (5)
H390.7935010.8750840.3214710.025*
C400.75015 (7)0.9225 (2)0.38183 (10)0.0195 (4)
H400.7609111.0130750.3885970.023*
C410.71472 (7)0.8726 (2)0.41182 (9)0.0150 (4)
H410.7019340.9284640.4396510.018*
C420.62263 (7)0.6412 (2)0.38994 (9)0.0119 (4)
C430.60479 (7)0.5061 (2)0.39284 (9)0.0131 (4)
H430.6146140.4386320.4184250.016*
C440.57219 (7)0.4812 (2)0.35561 (9)0.0121 (4)
C450.60324 (7)0.7194 (2)0.34919 (8)0.0127 (4)
C460.61135 (8)0.8665 (2)0.33321 (10)0.0179 (4)
H46A0.5835340.9161430.3312970.027*
H46B0.6301870.9104230.3607100.027*
H46C0.6256390.8693500.2971320.027*
C470.54704 (7)0.3538 (2)0.34963 (9)0.0132 (4)
C480.54585 (7)0.2589 (2)0.39318 (10)0.0154 (4)
H480.5604520.2785150.4267780.019*
C490.52323 (8)0.1363 (2)0.38677 (10)0.0183 (4)
H490.5226350.0731310.4167240.022*
C500.50267 (8)0.1932 (3)0.29910 (10)0.0217 (5)
H500.4877550.1704120.2660320.026*
C510.52412 (7)0.3199 (2)0.30223 (9)0.0186 (4)
H510.5230710.3826310.2721510.022*
C520.65133 (7)0.6757 (2)0.48315 (9)0.0136 (4)
C530.68559 (7)0.6962 (2)0.52585 (9)0.0156 (4)
C540.67439 (8)0.7577 (2)0.57610 (10)0.0209 (5)
H540.6457220.7924290.5813580.025*
C550.70475 (10)0.7684 (3)0.61842 (11)0.0274 (6)
H550.6969370.8115010.6521530.033*
C560.74651 (9)0.7159 (3)0.61127 (11)0.0285 (6)
H560.7670150.7206970.6405190.034*
C570.75827 (8)0.6566 (3)0.56166 (12)0.0268 (6)
H570.7870520.6225120.5567110.032*
C580.72815 (7)0.6466 (2)0.51880 (11)0.0206 (5)
H580.7365080.6061150.4847620.025*
C590.60868 (7)0.6238 (2)0.50397 (8)0.0124 (4)
C600.60408 (7)0.4899 (2)0.52820 (9)0.0132 (4)
H600.6281960.4334350.5380270.016*
C610.56173 (7)0.4509 (2)0.53587 (9)0.0133 (4)
H10.4224 (9)0.066 (2)0.6974 (11)0.016*
H5A0.4139 (9)0.100 (2)0.4414 (12)0.016*
C620.56924 (7)0.6876 (2)0.49598 (9)0.0134 (4)
C630.55977 (8)0.8281 (2)0.47279 (10)0.0186 (4)
H63A0.5452320.8846390.5007920.028*
H63B0.5871380.8725150.4618360.028*
H63C0.5407380.8188640.4405870.028*
C640.54454 (7)0.3176 (2)0.55485 (9)0.0130 (4)
C650.57048 (7)0.2262 (2)0.58573 (9)0.0162 (4)
H650.5993850.2509780.5957120.019*
C660.55344 (8)0.0998 (2)0.60141 (10)0.0196 (4)
H660.5713150.0388000.6221750.024*
C670.48805 (8)0.1469 (2)0.55973 (10)0.0194 (4)
H670.4591290.1196650.5508570.023*
C680.50226 (7)0.2752 (2)0.54203 (9)0.0165 (4)
H680.4834760.3336440.5214120.020*
O10.42684 (6)0.14814 (18)0.68867 (8)0.0245 (4)
O20.49097 (6)0.10773 (19)0.72974 (8)0.0298 (4)
O30.48516 (6)0.81129 (17)0.61804 (8)0.0217 (3)
O40.55357 (6)0.7784 (2)0.64753 (10)0.0318 (5)
C690.47882 (7)0.3264 (2)0.68692 (9)0.0142 (4)
C700.44885 (7)0.4129 (2)0.66074 (9)0.0163 (4)
H700.4202610.3804560.6530230.020*
C710.46080 (7)0.5464 (2)0.64599 (9)0.0158 (4)
H710.4402830.6052350.6284000.019*
C720.50264 (7)0.5942 (2)0.65683 (9)0.0148 (4)
C730.53254 (7)0.5075 (2)0.68283 (10)0.0184 (4)
H730.5612280.5395410.6901980.022*
C740.52056 (7)0.3745 (2)0.69799 (10)0.0174 (4)
H740.5409790.3161130.7160120.021*
C750.46670 (8)0.1825 (2)0.70418 (9)0.0170 (4)
C760.51661 (8)0.7369 (2)0.64045 (10)0.0177 (4)
O50.42313 (6)0.18035 (18)0.43155 (8)0.0252 (4)
O60.35541 (7)0.2063 (2)0.39963 (12)0.0519 (7)
O70.47593 (6)0.84965 (18)0.35910 (8)0.0227 (4)
H7A0.4800 (15)0.928 (3)0.3418 (18)0.083 (15)*
H3A0.4972 (16)0.887 (4)0.610 (2)0.099*
O80.41260 (7)0.8770 (2)0.31555 (11)0.0436 (6)
C770.40522 (8)0.3937 (2)0.38991 (10)0.0185 (4)
C780.44613 (7)0.4457 (2)0.40265 (10)0.0172 (4)
H780.4665050.3898800.4219860.021*
C790.45736 (7)0.5795 (2)0.38718 (10)0.0172 (4)
H790.4853800.6149850.3959880.021*
C800.42765 (8)0.6612 (2)0.35886 (9)0.0173 (4)
C810.38661 (8)0.6089 (3)0.34627 (11)0.0246 (5)
H810.3662280.6646070.3269040.029*
C820.37535 (8)0.4759 (3)0.36186 (11)0.0253 (5)
H820.3472200.4407000.3533910.030*
C830.39161 (8)0.2508 (3)0.40720 (11)0.0243 (5)
C840.43781 (8)0.8066 (2)0.34184 (10)0.0203 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0190 (2)0.0150 (2)0.0153 (2)0.00409 (19)0.0061 (2)0.0040 (2)
S20.0129 (2)0.0151 (2)0.0205 (3)0.00070 (19)0.00060 (19)0.0034 (2)
N10.0195 (9)0.0124 (9)0.0296 (11)0.0014 (7)0.0045 (8)0.0011 (8)
N20.0239 (10)0.0150 (9)0.0284 (11)0.0026 (8)0.0089 (8)0.0000 (8)
C10.0141 (9)0.0101 (9)0.0175 (10)0.0016 (7)0.0015 (8)0.0004 (8)
C20.0123 (9)0.0135 (9)0.0143 (9)0.0005 (7)0.0016 (7)0.0021 (7)
C30.0205 (11)0.0162 (10)0.0174 (10)0.0041 (8)0.0011 (8)0.0014 (8)
C40.0195 (11)0.0263 (12)0.0163 (10)0.0000 (9)0.0025 (9)0.0034 (9)
C50.0142 (10)0.0243 (11)0.0198 (11)0.0063 (8)0.0011 (8)0.0027 (9)
C60.0156 (10)0.0177 (10)0.0202 (11)0.0046 (8)0.0024 (8)0.0004 (9)
C70.0129 (9)0.0145 (9)0.0161 (10)0.0013 (7)0.0012 (7)0.0013 (8)
C80.0143 (9)0.0133 (9)0.0136 (9)0.0023 (7)0.0015 (7)0.0006 (7)
C90.0151 (9)0.0137 (9)0.0138 (9)0.0016 (7)0.0025 (8)0.0007 (7)
C100.0143 (9)0.0105 (9)0.0162 (10)0.0019 (7)0.0019 (8)0.0015 (8)
C110.0161 (10)0.0147 (10)0.0153 (10)0.0033 (8)0.0029 (8)0.0006 (8)
C120.0275 (12)0.0152 (10)0.0209 (11)0.0054 (9)0.0033 (9)0.0052 (9)
C130.0134 (9)0.0122 (9)0.0164 (10)0.0004 (7)0.0013 (8)0.0017 (8)
C140.0159 (10)0.0151 (10)0.0189 (10)0.0015 (8)0.0019 (8)0.0005 (8)
C150.0189 (11)0.0131 (10)0.0265 (12)0.0002 (8)0.0017 (9)0.0037 (9)
C160.0255 (12)0.0152 (10)0.0233 (11)0.0035 (9)0.0081 (9)0.0011 (8)
C170.0241 (11)0.0159 (10)0.0179 (10)0.0039 (9)0.0051 (9)0.0007 (8)
C180.0130 (9)0.0109 (9)0.0157 (10)0.0013 (7)0.0013 (7)0.0005 (7)
C190.0168 (10)0.0125 (9)0.0159 (9)0.0060 (7)0.0029 (8)0.0035 (8)
C200.0217 (11)0.0186 (10)0.0189 (11)0.0055 (9)0.0012 (9)0.0009 (8)
C210.0350 (14)0.0216 (12)0.0168 (11)0.0118 (10)0.0051 (10)0.0007 (9)
C220.0281 (13)0.0222 (11)0.0227 (12)0.0133 (10)0.0117 (10)0.0074 (9)
C230.0169 (10)0.0203 (11)0.0285 (12)0.0045 (9)0.0080 (9)0.0099 (9)
C240.0177 (10)0.0162 (10)0.0186 (11)0.0030 (8)0.0030 (8)0.0043 (8)
C250.0151 (9)0.0131 (9)0.0125 (9)0.0037 (7)0.0012 (7)0.0010 (7)
C260.0163 (10)0.0141 (9)0.0126 (9)0.0008 (7)0.0013 (8)0.0012 (8)
C270.0171 (10)0.0119 (9)0.0133 (9)0.0010 (7)0.0006 (8)0.0016 (7)
C280.0170 (10)0.0135 (9)0.0155 (10)0.0024 (8)0.0004 (8)0.0017 (8)
C290.0204 (11)0.0146 (10)0.0258 (12)0.0001 (8)0.0015 (9)0.0028 (9)
C300.0180 (10)0.0143 (10)0.0139 (10)0.0016 (8)0.0032 (8)0.0008 (8)
C310.0196 (11)0.0166 (10)0.0218 (11)0.0012 (8)0.0024 (9)0.0030 (9)
C320.0249 (12)0.0149 (10)0.0272 (12)0.0011 (9)0.0034 (10)0.0041 (9)
C330.0178 (11)0.0183 (11)0.0282 (13)0.0044 (8)0.0049 (9)0.0015 (9)
C340.0182 (10)0.0169 (10)0.0207 (11)0.0031 (8)0.0026 (8)0.0013 (8)
S30.0160 (2)0.0138 (2)0.0129 (2)0.00273 (18)0.00244 (19)0.00271 (19)
S40.0125 (2)0.0132 (2)0.0183 (2)0.00053 (18)0.00216 (19)0.00321 (19)
N30.0209 (9)0.0157 (9)0.0252 (10)0.0035 (7)0.0010 (8)0.0001 (8)
N40.0242 (10)0.0119 (8)0.0224 (10)0.0023 (7)0.0066 (8)0.0001 (7)
C350.0122 (9)0.0085 (8)0.0165 (10)0.0013 (7)0.0008 (7)0.0002 (7)
C360.0114 (9)0.0135 (9)0.0144 (9)0.0023 (7)0.0020 (7)0.0008 (7)
C370.0208 (11)0.0153 (10)0.0197 (10)0.0023 (8)0.0008 (9)0.0042 (8)
C380.0186 (11)0.0265 (12)0.0193 (11)0.0002 (9)0.0038 (9)0.0049 (9)
C390.0131 (10)0.0296 (12)0.0188 (11)0.0045 (9)0.0008 (8)0.0015 (9)
C400.0161 (10)0.0185 (10)0.0239 (11)0.0066 (8)0.0004 (9)0.0004 (9)
C410.0162 (10)0.0134 (10)0.0154 (10)0.0004 (8)0.0007 (8)0.0007 (8)
C420.0122 (9)0.0114 (9)0.0123 (9)0.0014 (7)0.0001 (7)0.0009 (7)
C430.0143 (9)0.0119 (9)0.0131 (9)0.0001 (7)0.0007 (7)0.0013 (7)
C440.0140 (9)0.0113 (9)0.0108 (9)0.0008 (7)0.0015 (7)0.0011 (7)
C450.0142 (9)0.0123 (9)0.0115 (9)0.0021 (7)0.0001 (7)0.0004 (7)
C460.0207 (11)0.0136 (10)0.0193 (11)0.0027 (8)0.0001 (9)0.0026 (8)
C470.0127 (9)0.0113 (9)0.0156 (10)0.0009 (7)0.0008 (7)0.0023 (7)
C480.0161 (10)0.0144 (10)0.0158 (10)0.0000 (8)0.0002 (8)0.0002 (8)
C490.0212 (11)0.0131 (10)0.0206 (11)0.0012 (8)0.0014 (9)0.0023 (8)
C500.0227 (11)0.0223 (11)0.0203 (11)0.0070 (9)0.0026 (9)0.0028 (9)
C510.0211 (11)0.0197 (11)0.0151 (10)0.0071 (8)0.0018 (8)0.0019 (8)
C520.0136 (9)0.0107 (9)0.0164 (10)0.0021 (7)0.0019 (8)0.0005 (7)
C530.0173 (10)0.0133 (9)0.0162 (10)0.0057 (7)0.0039 (8)0.0030 (8)
C540.0261 (12)0.0176 (11)0.0191 (11)0.0048 (9)0.0039 (9)0.0010 (8)
C550.0394 (15)0.0236 (12)0.0192 (12)0.0108 (11)0.0088 (11)0.0002 (9)
C560.0311 (14)0.0257 (12)0.0289 (13)0.0155 (11)0.0161 (11)0.0093 (10)
C570.0183 (11)0.0273 (13)0.0349 (14)0.0088 (9)0.0085 (10)0.0158 (11)
C580.0165 (10)0.0214 (11)0.0240 (11)0.0041 (8)0.0040 (9)0.0088 (9)
C590.0148 (9)0.0126 (9)0.0097 (9)0.0022 (7)0.0007 (7)0.0000 (7)
C600.0151 (9)0.0123 (9)0.0123 (9)0.0013 (7)0.0011 (7)0.0016 (7)
C610.0156 (9)0.0119 (9)0.0124 (9)0.0016 (7)0.0002 (8)0.0020 (8)
C620.0151 (10)0.0120 (9)0.0131 (9)0.0028 (8)0.0014 (8)0.0006 (7)
C630.0219 (11)0.0112 (9)0.0228 (11)0.0018 (8)0.0025 (9)0.0034 (8)
C640.0155 (10)0.0112 (9)0.0123 (9)0.0012 (7)0.0033 (7)0.0017 (7)
C650.0174 (10)0.0157 (10)0.0155 (10)0.0011 (8)0.0012 (8)0.0019 (8)
C660.0227 (11)0.0142 (10)0.0219 (11)0.0010 (8)0.0028 (9)0.0035 (9)
C670.0200 (11)0.0157 (10)0.0226 (11)0.0054 (8)0.0048 (9)0.0000 (9)
C680.0159 (10)0.0151 (10)0.0184 (11)0.0008 (8)0.0015 (8)0.0015 (8)
O10.0238 (9)0.0134 (8)0.0362 (10)0.0058 (7)0.0029 (8)0.0066 (7)
O20.0352 (10)0.0193 (8)0.0348 (11)0.0064 (7)0.0113 (9)0.0108 (8)
O30.0205 (8)0.0121 (7)0.0324 (9)0.0014 (6)0.0022 (7)0.0054 (7)
O40.0221 (9)0.0210 (9)0.0523 (13)0.0071 (7)0.0050 (9)0.0090 (9)
C690.0188 (10)0.0119 (9)0.0118 (9)0.0005 (8)0.0020 (8)0.0007 (7)
C700.0163 (10)0.0148 (10)0.0179 (10)0.0022 (8)0.0018 (8)0.0019 (8)
C710.0159 (10)0.0137 (9)0.0177 (10)0.0014 (8)0.0013 (8)0.0036 (8)
C720.0148 (9)0.0122 (9)0.0173 (10)0.0011 (7)0.0034 (8)0.0006 (8)
C730.0143 (10)0.0159 (10)0.0250 (12)0.0017 (8)0.0003 (9)0.0019 (9)
C740.0184 (10)0.0141 (10)0.0197 (11)0.0012 (8)0.0006 (8)0.0026 (8)
C750.0243 (11)0.0144 (10)0.0122 (10)0.0030 (8)0.0018 (8)0.0007 (8)
C760.0186 (10)0.0138 (10)0.0208 (11)0.0014 (8)0.0025 (9)0.0009 (8)
O50.0210 (9)0.0130 (8)0.0415 (11)0.0006 (6)0.0055 (8)0.0076 (7)
O60.0362 (12)0.0344 (12)0.0850 (19)0.0214 (10)0.0236 (12)0.0279 (12)
O70.0208 (8)0.0173 (8)0.0300 (9)0.0049 (7)0.0040 (7)0.0029 (7)
O80.0422 (12)0.0286 (10)0.0600 (14)0.0130 (9)0.0293 (11)0.0241 (10)
C770.0183 (10)0.0177 (10)0.0196 (11)0.0037 (8)0.0005 (9)0.0027 (9)
C780.0145 (10)0.0162 (10)0.0209 (11)0.0008 (8)0.0020 (8)0.0027 (8)
C790.0126 (9)0.0165 (10)0.0226 (11)0.0025 (8)0.0015 (8)0.0012 (8)
C800.0216 (11)0.0142 (10)0.0162 (10)0.0049 (8)0.0021 (8)0.0012 (8)
C810.0234 (12)0.0243 (12)0.0260 (13)0.0039 (9)0.0068 (10)0.0075 (10)
C820.0207 (11)0.0248 (12)0.0306 (13)0.0074 (9)0.0094 (10)0.0065 (10)
C830.0227 (12)0.0205 (12)0.0296 (13)0.0070 (9)0.0001 (10)0.0063 (10)
C840.0222 (11)0.0186 (11)0.0200 (11)0.0052 (9)0.0043 (9)0.0041 (9)
Geometric parameters (Å, º) top
S1—C101.724 (2)C39—C401.383 (3)
S1—C111.728 (2)C40—H400.9500
S2—C271.731 (2)C40—C411.394 (3)
S2—C281.721 (2)C41—H410.9500
N1—C151.335 (3)C42—C431.418 (3)
N1—C161.342 (3)C42—C451.380 (3)
N2—C321.343 (3)C43—H430.9500
N2—C331.330 (3)C43—C441.369 (3)
C1—C21.493 (3)C44—C471.460 (3)
C1—C81.488 (3)C45—C461.495 (3)
C1—C181.358 (3)C46—H46A0.9800
C2—C31.396 (3)C46—H46B0.9800
C2—C71.400 (3)C46—H46C0.9800
C3—H30.9500C47—C481.401 (3)
C3—C41.388 (3)C47—C511.388 (3)
C4—H40.9500C48—H480.9500
C4—C51.388 (3)C48—C491.382 (3)
C5—H50.9500C49—H490.9500
C5—C61.385 (3)C50—H500.9500
C6—H60.9500C50—C511.393 (3)
C6—C71.394 (3)C51—H510.9500
C7—H70.9500C52—C531.490 (3)
C8—C91.422 (3)C52—C591.489 (3)
C8—C111.374 (3)C53—C541.400 (3)
C9—H90.9500C53—C581.401 (3)
C9—C101.361 (3)C54—H540.9500
C10—C131.461 (3)C54—C551.391 (3)
C11—C121.501 (3)C55—H550.9500
C12—H12A0.9800C55—C561.389 (4)
C12—H12B0.9800C56—H560.9500
C12—H12C0.9800C56—C571.382 (4)
C13—C141.404 (3)C57—H570.9500
C13—C171.396 (3)C57—C581.395 (3)
C14—H140.9500C58—H580.9500
C14—C151.381 (3)C59—C601.429 (3)
C15—H150.9500C59—C621.372 (3)
C16—H160.9500C60—H600.9500
C16—C171.392 (3)C60—C611.365 (3)
C17—H170.9500C61—C641.467 (3)
C18—C191.488 (3)C62—C631.498 (3)
C18—C251.486 (3)C63—H63A0.9800
C19—C201.404 (3)C63—H63B0.9800
C19—C241.400 (3)C63—H63C0.9800
C20—H200.9500C64—C651.406 (3)
C20—C211.387 (3)C64—C681.396 (3)
C21—H210.9500C65—H650.9500
C21—C221.392 (4)C65—C661.383 (3)
C22—H220.9500C66—H660.9500
C22—C231.385 (4)C67—H670.9500
C23—H230.9500C67—C681.383 (3)
C23—C241.392 (3)C68—H680.9500
C24—H240.9500O1—H10.83 (2)
C25—C261.434 (3)O1—C751.322 (3)
C25—C281.372 (3)O2—C751.209 (3)
C26—H260.9500O3—C761.321 (3)
C26—C271.370 (3)O3—H3A0.84 (3)
C27—C301.459 (3)O4—C761.215 (3)
C28—C291.499 (3)C69—C701.396 (3)
C29—H29A0.9800C69—C741.388 (3)
C29—H29B0.9800C69—C751.500 (3)
C29—H29C0.9800C70—H700.9500
C30—C311.395 (3)C70—C711.388 (3)
C30—C341.402 (3)C71—H710.9500
C31—H310.9500C71—C721.389 (3)
C31—C321.390 (3)C72—C731.394 (3)
C32—H320.9500C72—C761.499 (3)
C33—H330.9500C73—H730.9500
C33—C341.385 (3)C73—C741.387 (3)
C34—H340.9500C74—H740.9500
S3—C441.731 (2)O5—H5A0.86 (2)
S3—C451.725 (2)O5—C831.322 (3)
S4—C611.732 (2)O6—C831.205 (3)
S4—C621.722 (2)O7—H7A0.88 (2)
N3—C491.338 (3)O7—C841.310 (3)
N3—C501.337 (3)O8—C841.212 (3)
N4—C661.344 (3)C77—C781.387 (3)
N4—C671.339 (3)C77—C821.391 (3)
C35—C361.492 (3)C77—C831.503 (3)
C35—C421.491 (3)C78—H780.9500
C35—C521.353 (3)C78—C791.390 (3)
C36—C371.402 (3)C79—H790.9500
C36—C411.394 (3)C79—C801.388 (3)
C37—H370.9500C80—C811.391 (3)
C37—C381.390 (3)C80—C841.499 (3)
C38—H380.9500C81—H810.9500
C38—C391.384 (3)C81—C821.384 (3)
C39—H390.9500C82—H820.9500
C10—S1—C1192.46 (10)C45—C42—C35125.98 (19)
C28—S2—C2792.64 (11)C45—C42—C43111.97 (19)
C15—N1—C16117.2 (2)C42—C43—H43122.9
C33—N2—C32117.7 (2)C44—C43—C42114.29 (19)
C8—C1—C2113.47 (18)C44—C43—H43122.9
C18—C1—C2126.6 (2)C43—C44—S3110.08 (16)
C18—C1—C8119.84 (19)C43—C44—C47126.9 (2)
C3—C2—C1118.59 (19)C47—C44—S3123.04 (16)
C3—C2—C7119.0 (2)C42—C45—S3111.10 (15)
C7—C2—C1122.16 (19)C42—C45—C46129.5 (2)
C2—C3—H3119.6C46—C45—S3119.39 (16)
C4—C3—C2120.7 (2)C45—C46—H46A109.5
C4—C3—H3119.6C45—C46—H46B109.5
C3—C4—H4120.1C45—C46—H46C109.5
C3—C4—C5119.8 (2)H46A—C46—H46B109.5
C5—C4—H4120.1H46A—C46—H46C109.5
C4—C5—H5120.0H46B—C46—H46C109.5
C6—C5—C4120.1 (2)C48—C47—C44119.43 (19)
C6—C5—H5120.0C51—C47—C44123.3 (2)
C5—C6—H6119.8C51—C47—C48117.2 (2)
C5—C6—C7120.3 (2)C47—C48—H48120.3
C7—C6—H6119.8C49—C48—C47119.4 (2)
C2—C7—H7120.0C49—C48—H48120.3
C6—C7—C2119.9 (2)N3—C49—C48123.3 (2)
C6—C7—H7120.0N3—C49—H49118.3
C9—C8—C1121.76 (19)C48—C49—H49118.3
C11—C8—C1126.17 (19)N3—C50—H50118.5
C11—C8—C9112.03 (19)N3—C50—C51123.0 (2)
C8—C9—H9123.0C51—C50—H50118.5
C10—C9—C8114.05 (19)C47—C51—C50119.5 (2)
C10—C9—H9123.0C47—C51—H51120.2
C9—C10—S1110.49 (16)C50—C51—H51120.2
C9—C10—C13125.6 (2)C35—C52—C53125.1 (2)
C13—C10—S1123.89 (16)C35—C52—C59119.30 (19)
C8—C11—S1110.97 (16)C59—C52—C53115.35 (18)
C8—C11—C12128.9 (2)C54—C53—C52119.4 (2)
C12—C11—S1120.05 (17)C54—C53—C58118.7 (2)
C11—C12—H12A109.5C58—C53—C52121.8 (2)
C11—C12—H12B109.5C53—C54—H54119.6
C11—C12—H12C109.5C55—C54—C53120.8 (2)
H12A—C12—H12B109.5C55—C54—H54119.6
H12A—C12—H12C109.5C54—C55—H55120.1
H12B—C12—H12C109.5C56—C55—C54119.9 (3)
C14—C13—C10119.6 (2)C56—C55—H55120.1
C17—C13—C10122.9 (2)C55—C56—H56120.0
C17—C13—C14117.5 (2)C57—C56—C55120.1 (2)
C13—C14—H14120.5C57—C56—H56120.0
C15—C14—C13119.0 (2)C56—C57—H57119.8
C15—C14—H14120.5C56—C57—C58120.4 (3)
N1—C15—C14123.9 (2)C58—C57—H57119.8
N1—C15—H15118.1C53—C58—H58119.9
C14—C15—H15118.1C57—C58—C53120.1 (2)
N1—C16—H16118.3C57—C58—H58119.9
N1—C16—C17123.5 (2)C60—C59—C52122.09 (19)
C17—C16—H16118.3C62—C59—C52125.13 (19)
C13—C17—H17120.5C62—C59—C60112.24 (19)
C16—C17—C13118.9 (2)C59—C60—H60123.2
C16—C17—H17120.5C61—C60—C59113.60 (19)
C1—C18—C19125.8 (2)C61—C60—H60123.2
C1—C18—C25118.50 (19)C60—C61—S4110.37 (15)
C25—C18—C19115.41 (18)C60—C61—C64128.9 (2)
C20—C19—C18119.5 (2)C64—C61—S4120.65 (16)
C24—C19—C18121.5 (2)C59—C62—S4111.18 (16)
C24—C19—C20118.6 (2)C59—C62—C63129.2 (2)
C19—C20—H20119.6C63—C62—S4119.63 (16)
C21—C20—C19120.7 (2)C62—C63—H63A109.5
C21—C20—H20119.6C62—C63—H63B109.5
C20—C21—H21120.0C62—C63—H63C109.5
C20—C21—C22120.1 (2)H63A—C63—H63B109.5
C22—C21—H21120.0H63A—C63—H63C109.5
C21—C22—H22120.1H63B—C63—H63C109.5
C23—C22—C21119.8 (2)C65—C64—C61121.11 (19)
C23—C22—H22120.1C68—C64—C61121.5 (2)
C22—C23—H23119.7C68—C64—C65117.4 (2)
C22—C23—C24120.6 (2)C64—C65—H65120.4
C24—C23—H23119.7C66—C65—C64119.3 (2)
C19—C24—H24119.9C66—C65—H65120.4
C23—C24—C19120.2 (2)N4—C66—C65123.1 (2)
C23—C24—H24119.9N4—C66—H66118.4
C26—C25—C18121.91 (19)C65—C66—H66118.4
C28—C25—C18125.28 (19)N4—C67—H67118.2
C28—C25—C26112.20 (19)N4—C67—C68123.6 (2)
C25—C26—H26123.3C68—C67—H67118.2
C27—C26—C25113.35 (19)C64—C68—H68120.4
C27—C26—H26123.3C67—C68—C64119.2 (2)
C26—C27—S2110.41 (16)C67—C68—H68120.4
C26—C27—C30128.5 (2)C75—O1—H1108.7 (19)
C30—C27—S2120.99 (16)C76—O3—H3A104 (4)
C25—C28—S2111.29 (16)C70—C69—C75121.3 (2)
C25—C28—C29129.1 (2)C74—C69—C70119.7 (2)
C29—C28—S2119.55 (17)C74—C69—C75119.0 (2)
C28—C29—H29A109.5C69—C70—H70120.0
C28—C29—H29B109.5C71—C70—C69120.0 (2)
C28—C29—H29C109.5C71—C70—H70120.0
H29A—C29—H29B109.5C70—C71—H71119.9
H29A—C29—H29C109.5C70—C71—C72120.3 (2)
H29B—C29—H29C109.5C72—C71—H71119.9
C31—C30—C27121.4 (2)C71—C72—C73119.6 (2)
C31—C30—C34117.2 (2)C71—C72—C76121.4 (2)
C34—C30—C27121.4 (2)C73—C72—C76119.1 (2)
C30—C31—H31120.3C72—C73—H73119.9
C32—C31—C30119.3 (2)C74—C73—C72120.2 (2)
C32—C31—H31120.3C74—C73—H73119.9
N2—C32—C31123.1 (2)C69—C74—H74119.9
N2—C32—H32118.5C73—C74—C69120.2 (2)
C31—C32—H32118.5C73—C74—H74119.9
N2—C33—H33118.3O1—C75—C69112.5 (2)
N2—C33—C34123.4 (2)O2—C75—O1124.4 (2)
C34—C33—H33118.3O2—C75—C69123.1 (2)
C30—C34—H34120.3O3—C76—C72113.69 (19)
C33—C34—C30119.3 (2)O4—C76—O3124.1 (2)
C33—C34—H34120.3O4—C76—C72122.2 (2)
C45—S3—C4492.56 (10)C83—O5—H5A110.5 (19)
C62—S4—C6192.53 (10)C84—O7—H7A104 (3)
C50—N3—C49117.6 (2)C78—C77—C82119.9 (2)
C67—N4—C66117.5 (2)C78—C77—C83121.5 (2)
C42—C35—C36115.30 (18)C82—C77—C83118.6 (2)
C52—C35—C36125.57 (19)C77—C78—H78120.0
C52—C35—C42119.05 (19)C77—C78—C79120.1 (2)
C37—C36—C35118.78 (19)C79—C78—H78120.0
C41—C36—C35122.39 (19)C78—C79—H79120.0
C41—C36—C37118.7 (2)C80—C79—C78120.0 (2)
C36—C37—H37119.8C80—C79—H79120.0
C38—C37—C36120.4 (2)C79—C80—C81119.7 (2)
C38—C37—H37119.8C79—C80—C84122.3 (2)
C37—C38—H38120.0C81—C80—C84118.0 (2)
C39—C38—C37120.1 (2)C80—C81—H81119.9
C39—C38—H38120.0C82—C81—C80120.2 (2)
C38—C39—H39119.9C82—C81—H81119.9
C40—C39—C38120.1 (2)C77—C82—H82120.0
C40—C39—H39119.9C81—C82—C77120.0 (2)
C39—C40—H40120.0C81—C82—H82120.0
C39—C40—C41120.1 (2)O5—C83—C77113.3 (2)
C41—C40—H40120.0O6—C83—O5123.9 (2)
C36—C41—C40120.5 (2)O6—C83—C77122.8 (2)
C36—C41—H41119.8O7—C84—C80113.3 (2)
C40—C41—H41119.8O8—C84—O7124.0 (2)
C43—C42—C35122.04 (19)O8—C84—C80122.7 (2)
S1—C10—C13—C14153.33 (18)C36—C35—C52—C59178.90 (19)
S1—C10—C13—C1727.6 (3)C36—C37—C38—C391.8 (4)
S2—C27—C30—C31163.93 (18)C37—C36—C41—C402.5 (3)
S2—C27—C30—C3417.5 (3)C37—C38—C39—C402.7 (4)
N1—C16—C17—C130.2 (4)C38—C39—C40—C411.0 (4)
N2—C33—C34—C300.1 (4)C39—C40—C41—C361.7 (4)
C1—C2—C3—C4173.0 (2)C41—C36—C37—C380.8 (3)
C1—C2—C7—C6172.1 (2)C42—C35—C36—C3751.9 (3)
C1—C8—C9—C10177.7 (2)C42—C35—C36—C41124.5 (2)
C1—C8—C11—S1177.39 (18)C42—C35—C52—C53169.29 (19)
C1—C8—C11—C125.3 (4)C42—C35—C52—C594.5 (3)
C1—C18—C19—C20146.8 (2)C42—C43—C44—S30.5 (2)
C1—C18—C19—C2439.8 (3)C42—C43—C44—C47178.4 (2)
C1—C18—C25—C26111.9 (2)C43—C42—C45—S30.4 (2)
C1—C18—C25—C2858.5 (3)C43—C42—C45—C46178.4 (2)
C2—C1—C8—C9125.3 (2)C43—C44—C47—C4819.1 (3)
C2—C1—C8—C1152.3 (3)C43—C44—C47—C51160.3 (2)
C2—C1—C18—C199.3 (4)C44—S3—C45—C420.11 (17)
C2—C1—C18—C25177.48 (19)C44—S3—C45—C46178.34 (18)
C2—C3—C4—C50.6 (4)C44—C47—C48—C49177.9 (2)
C3—C2—C7—C62.1 (3)C44—C47—C51—C50177.0 (2)
C3—C4—C5—C61.9 (4)C45—S3—C44—C430.20 (17)
C4—C5—C6—C71.2 (4)C45—S3—C44—C47178.71 (19)
C5—C6—C7—C20.9 (3)C45—C42—C43—C440.6 (3)
C7—C2—C3—C41.4 (3)C47—C48—C49—N30.2 (3)
C8—C1—C2—C345.1 (3)C48—C47—C51—C502.4 (3)
C8—C1—C2—C7129.1 (2)C49—N3—C50—C510.2 (4)
C8—C1—C18—C19166.1 (2)C50—N3—C49—C481.1 (4)
C8—C1—C18—C257.0 (3)C51—C47—C48—C491.5 (3)
C8—C9—C10—S10.1 (2)C52—C35—C36—C37124.9 (2)
C8—C9—C10—C13179.6 (2)C52—C35—C36—C4158.8 (3)
C9—C8—C11—S10.4 (2)C52—C35—C42—C4352.9 (3)
C9—C8—C11—C12176.9 (2)C52—C35—C42—C45125.7 (2)
C9—C10—C13—C1427.3 (3)C52—C53—C54—C55174.9 (2)
C9—C10—C13—C17151.9 (2)C52—C53—C58—C57174.1 (2)
C10—S1—C11—C80.39 (18)C52—C59—C60—C61169.05 (19)
C10—S1—C11—C12177.2 (2)C52—C59—C62—S4169.36 (17)
C10—C13—C14—C15179.4 (2)C52—C59—C62—C639.4 (4)
C10—C13—C17—C16179.0 (2)C53—C52—C59—C6065.0 (3)
C11—S1—C10—C90.28 (18)C53—C52—C59—C62124.1 (2)
C11—S1—C10—C13179.8 (2)C53—C54—C55—C561.0 (4)
C11—C8—C9—C100.2 (3)C54—C53—C58—C571.1 (3)
C13—C14—C15—N10.7 (4)C54—C55—C56—C571.8 (4)
C14—C13—C17—C160.2 (3)C55—C56—C57—C581.2 (4)
C15—N1—C16—C170.3 (4)C56—C57—C58—C530.2 (3)
C16—N1—C15—C140.7 (3)C58—C53—C54—C550.5 (3)
C17—C13—C14—C150.2 (3)C59—C52—C53—C5442.7 (3)
C18—C1—C2—C3130.6 (2)C59—C52—C53—C58132.5 (2)
C18—C1—C2—C755.2 (3)C59—C60—C61—S42.1 (2)
C18—C1—C8—C950.8 (3)C59—C60—C61—C64174.1 (2)
C18—C1—C8—C11131.6 (2)C60—C59—C62—S42.3 (2)
C18—C19—C20—C21174.1 (2)C60—C59—C62—C63178.9 (2)
C18—C19—C24—C23173.7 (2)C60—C61—C64—C6522.4 (4)
C18—C25—C26—C27168.0 (2)C60—C61—C64—C68156.1 (2)
C18—C25—C28—S2168.48 (17)C61—S4—C62—C590.98 (18)
C18—C25—C28—C2910.0 (4)C61—S4—C62—C63179.87 (19)
C19—C18—C25—C2662.0 (3)C61—C64—C65—C66178.1 (2)
C19—C18—C25—C28127.6 (2)C61—C64—C68—C67178.3 (2)
C19—C20—C21—C221.0 (4)C62—S4—C61—C600.67 (18)
C20—C19—C24—C230.2 (3)C62—S4—C61—C64175.89 (19)
C20—C21—C22—C231.2 (4)C62—C59—C60—C612.9 (3)
C21—C22—C23—C240.9 (4)C64—C65—C66—N40.2 (4)
C22—C23—C24—C190.4 (3)C65—C64—C68—C670.3 (3)
C24—C19—C20—C210.5 (3)C66—N4—C67—C680.7 (4)
C25—C18—C19—C2039.8 (3)C67—N4—C66—C650.5 (4)
C25—C18—C19—C24133.6 (2)C68—C64—C65—C660.6 (3)
C25—C26—C27—S22.7 (2)C69—C70—C71—C720.4 (3)
C25—C26—C27—C30173.3 (2)C70—C69—C74—C730.4 (3)
C26—C25—C28—S22.7 (2)C70—C69—C75—O14.0 (3)
C26—C25—C28—C29178.8 (2)C70—C69—C75—O2175.6 (2)
C26—C27—C30—C3120.5 (4)C70—C71—C72—C730.2 (3)
C26—C27—C30—C34158.2 (2)C70—C71—C72—C76178.9 (2)
C27—S2—C28—C251.02 (18)C71—C72—C73—C740.3 (3)
C27—S2—C28—C29179.67 (19)C71—C72—C76—O33.2 (3)
C27—C30—C31—C32177.8 (2)C71—C72—C76—O4176.9 (2)
C27—C30—C34—C33177.8 (2)C72—C73—C74—C690.6 (4)
C28—S2—C27—C261.00 (18)C73—C72—C76—O3177.6 (2)
C28—S2—C27—C30175.34 (18)C73—C72—C76—O42.3 (4)
C28—C25—C26—C273.6 (3)C74—C69—C70—C710.1 (3)
C30—C31—C32—N20.0 (4)C74—C69—C75—O1176.9 (2)
C31—C30—C34—C330.9 (3)C74—C69—C75—O23.6 (3)
C32—N2—C33—C340.8 (4)C75—C69—C70—C71179.0 (2)
C33—N2—C32—C310.9 (4)C75—C69—C74—C73179.6 (2)
C34—C30—C31—C320.9 (3)C76—C72—C73—C74179.5 (2)
S3—C44—C47—C48159.66 (17)C77—C78—C79—C800.1 (4)
S3—C44—C47—C5121.0 (3)C78—C77—C82—C810.6 (4)
S4—C61—C64—C65161.69 (17)C78—C77—C83—O54.3 (4)
S4—C61—C64—C6819.7 (3)C78—C77—C83—O6175.3 (3)
N3—C50—C51—C471.6 (4)C78—C79—C80—C810.3 (4)
N4—C67—C68—C640.3 (4)C78—C79—C80—C84179.2 (2)
C35—C36—C37—C38175.7 (2)C79—C80—C81—C820.0 (4)
C35—C36—C41—C40173.8 (2)C79—C80—C84—O73.7 (3)
C35—C42—C43—C44178.19 (19)C79—C80—C84—O8177.5 (3)
C35—C42—C45—S3178.30 (17)C80—C81—C82—C770.4 (4)
C35—C42—C45—C460.3 (4)C81—C80—C84—O7175.2 (2)
C35—C52—C53—C54143.3 (2)C81—C80—C84—O83.5 (4)
C35—C52—C53—C5841.5 (3)C82—C77—C78—C790.3 (4)
C35—C52—C59—C60109.3 (2)C82—C77—C83—O5177.5 (2)
C35—C52—C59—C6261.6 (3)C82—C77—C83—O62.9 (4)
C36—C35—C42—C43124.1 (2)C83—C77—C78—C79178.5 (2)
C36—C35—C42—C4557.4 (3)C83—C77—C82—C81178.8 (2)
C36—C35—C52—C537.3 (3)C84—C80—C81—C82179.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N1i0.83 (2)1.85 (2)2.650 (3)161 (3)
O5—H5A···N2i0.86 (2)1.77 (2)2.636 (3)178 (3)
O7—H7A···N3ii0.88 (2)1.81 (3)2.609 (3)150 (5)
O3—H3A···N4ii0.84 (3)1.81 (3)2.639 (2)169 (5)
Symmetry codes: (i) x1/2, y+1/2, z; (ii) x, y1, z.
(dte-7) top
Crystal data top
C68H56CoN4O2S4Dx = 1.070 Mg m3
Mr = 1148.33Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, FdddCell parameters from 9970 reflections
a = 9.8404 (4) Åθ = 2.3–26.2°
b = 21.4458 (8) ŵ = 0.40 mm1
c = 67.537 (3) ÅT = 90 K
V = 14252.6 (10) Å3Prism, colourless
Z = 80.06 × 0.06 × 0.02 mm
F(000) = 4792
Data collection top
Bruker APEX-II CCD
diffractometer
3390 reflections with I > 2σ(I)
φ and ω scansRint = 0.047
Absorption correction: multi-scan
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1167 before and 0.0596 after correction. The Ratio of minimum to maximum transmission is 0.8919. The λ/2 correction factor is Not present.
θmax = 28.3°, θmin = 2.0°
Tmin = 0.665, Tmax = 0.746h = 1313
29065 measured reflectionsk = 2827
4446 independent reflectionsl = 9054
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.048H-atom parameters constrained
wR(F2) = 0.114 w = 1/[σ2(Fo2) + (0.0341P)2 + 47.4853P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.003
4446 reflectionsΔρmax = 0.58 e Å3
182 parametersΔρmin = 0.66 e Å3
0 restraints
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)
Co10.6250000.1250000.6250000.0605 (3)
S10.55657 (5)0.38490 (3)0.55195 (2)0.03477 (14)
O10.8380 (3)0.1250000.6250000.0650 (8)
H1A0.9025380.0941140.6187180.098*0.5
H1B0.9025380.1559360.6312620.098*0.5
N10.6375 (3)0.19489 (9)0.60233 (2)0.0603 (7)
C10.80629 (19)0.37441 (8)0.50525 (2)0.0258 (4)
C20.7236 (2)0.37812 (9)0.48671 (2)0.0289 (4)
C30.6153 (2)0.33763 (10)0.48373 (3)0.0351 (5)
H30.5947210.3071010.4934760.042*
C40.5364 (2)0.34124 (11)0.46663 (3)0.0437 (6)
H40.4638480.3127110.4646560.052*
C50.5636 (2)0.38623 (11)0.45252 (3)0.0445 (6)
H50.5095710.3888920.4409020.053*
C60.6694 (2)0.42713 (11)0.45541 (3)0.0407 (6)
H60.6879390.4581750.4457520.049*
C70.7497 (2)0.42350 (10)0.47238 (3)0.0338 (5)
H70.8225560.4520120.4741980.041*
C80.72822 (19)0.36796 (8)0.52400 (2)0.0252 (4)
C90.7548 (2)0.32146 (9)0.53852 (2)0.0275 (4)
H90.8251140.2913730.5372380.033*
C100.6696 (2)0.32414 (9)0.55451 (3)0.0299 (4)
C110.6208 (2)0.40515 (9)0.52922 (3)0.0309 (4)
C120.5567 (2)0.45714 (11)0.51779 (3)0.0457 (6)
H12A0.5130690.4862690.5269820.069*
H12B0.4884730.4400770.5087200.069*
H12C0.6266880.4791310.5101810.069*
C130.6613 (2)0.28161 (9)0.57142 (3)0.0367 (5)
C140.7430 (3)0.22917 (11)0.57232 (3)0.0579 (8)
H140.8090720.2217860.5623430.070*
C150.7281 (4)0.18787 (12)0.58770 (3)0.0705 (10)
H150.7853440.1522230.5879820.085*
C160.5600 (3)0.24552 (11)0.60151 (3)0.0578 (7)
H160.4955570.2519160.6117830.069*
C170.5676 (3)0.28933 (11)0.58662 (3)0.0487 (6)
H170.5092010.3245940.5867520.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.1338 (8)0.0323 (3)0.0154 (3)0.0000.0000.000
S10.0360 (3)0.0427 (3)0.0257 (2)0.0163 (2)0.0078 (2)0.0025 (2)
O10.118 (3)0.0462 (14)0.0306 (11)0.0000.0000.0010 (10)
N10.125 (2)0.0353 (10)0.0206 (8)0.0184 (12)0.0178 (11)0.0010 (7)
C10.0346 (10)0.0259 (9)0.0168 (7)0.0160 (8)0.0004 (7)0.0001 (7)
C20.0348 (10)0.0340 (10)0.0180 (8)0.0213 (8)0.0015 (7)0.0016 (7)
C30.0417 (12)0.0373 (11)0.0264 (9)0.0163 (9)0.0065 (9)0.0009 (8)
C40.0486 (13)0.0483 (13)0.0341 (11)0.0188 (11)0.0146 (10)0.0086 (10)
C50.0517 (14)0.0597 (14)0.0221 (9)0.0321 (12)0.0120 (9)0.0069 (9)
C60.0504 (13)0.0533 (13)0.0184 (9)0.0318 (11)0.0033 (9)0.0042 (9)
C70.0379 (11)0.0420 (11)0.0215 (8)0.0225 (9)0.0037 (8)0.0032 (8)
C80.0306 (9)0.0278 (9)0.0172 (7)0.0103 (8)0.0034 (7)0.0016 (7)
C90.0361 (10)0.0284 (9)0.0180 (8)0.0133 (8)0.0005 (7)0.0021 (7)
C100.0421 (11)0.0288 (9)0.0189 (8)0.0091 (8)0.0012 (8)0.0025 (7)
C110.0323 (10)0.0376 (11)0.0226 (8)0.0137 (9)0.0030 (8)0.0041 (8)
C120.0511 (14)0.0503 (13)0.0357 (11)0.0323 (11)0.0100 (10)0.0090 (10)
C130.0602 (14)0.0317 (10)0.0181 (8)0.0070 (10)0.0043 (9)0.0017 (7)
C140.098 (2)0.0496 (14)0.0264 (10)0.0351 (14)0.0215 (12)0.0105 (10)
C150.135 (3)0.0476 (14)0.0292 (11)0.0425 (17)0.0250 (15)0.0113 (10)
C160.104 (2)0.0427 (13)0.0265 (10)0.0126 (14)0.0246 (12)0.0003 (9)
C170.0813 (18)0.0383 (12)0.0267 (10)0.0166 (12)0.0172 (11)0.0029 (9)
Geometric parameters (Å, º) top
Co1—O12.096 (3)C5—C61.375 (3)
Co1—O1i2.096 (3)C6—H60.9500
Co1—N1i2.1458 (18)C6—C71.394 (3)
Co1—N1ii2.1458 (18)C7—H70.9500
Co1—N12.1459 (18)C8—C91.423 (2)
Co1—N1iii2.1458 (18)C8—C111.370 (3)
S1—C101.7218 (19)C9—H90.9500
S1—C111.7163 (19)C9—C101.368 (2)
O1—H1A1.0111C10—C131.464 (3)
O1—H1B1.0112C11—C121.495 (3)
N1—C151.339 (3)C12—H12A0.9800
N1—C161.328 (3)C12—H12B0.9800
C1—C1iv1.353 (4)C12—H12C0.9800
C1—C21.495 (2)C13—C141.384 (3)
C1—C81.487 (2)C13—C171.389 (3)
C2—C31.389 (3)C14—H140.9500
C2—C71.397 (3)C14—C151.373 (3)
C3—H30.9500C15—H150.9500
C3—C41.394 (3)C16—H160.9500
C4—H40.9500C16—C171.378 (3)
C4—C51.382 (3)C17—H170.9500
C5—H50.9500
O1—Co1—O1i180.0C5—C6—C7120.7 (2)
O1—Co1—N1ii93.27 (8)C7—C6—H6119.7
O1i—Co1—N1iii93.27 (8)C2—C7—H7119.9
O1i—Co1—N193.27 (7)C6—C7—C2120.3 (2)
O1—Co1—N1i93.27 (7)C6—C7—H7119.9
O1i—Co1—N1ii86.73 (7)C9—C8—C1123.85 (15)
O1i—Co1—N1i86.73 (8)C11—C8—C1124.29 (16)
O1—Co1—N186.73 (8)C11—C8—C9111.85 (16)
O1—Co1—N1iii86.73 (7)C8—C9—H9123.2
N1iii—Co1—N1173.45 (15)C10—C9—C8113.70 (16)
N1ii—Co1—N1iii88.99 (10)C10—C9—H9123.2
N1ii—Co1—N191.39 (10)C9—C10—S1110.39 (14)
N1i—Co1—N1ii173.45 (15)C9—C10—C13128.60 (18)
N1i—Co1—N188.98 (10)C13—C10—S1120.91 (15)
N1i—Co1—N1iii91.39 (10)C8—C11—S1111.53 (13)
C11—S1—C1092.49 (9)C8—C11—C12128.79 (17)
Co1—O1—H1A128.9C12—C11—S1119.67 (14)
Co1—O1—H1B128.9C11—C12—H12A109.5
H1A—O1—H1B102.2C11—C12—H12B109.5
C15—N1—Co1119.07 (16)C11—C12—H12C109.5
C16—N1—Co1124.63 (16)H12A—C12—H12B109.5
C16—N1—C15116.3 (2)H12A—C12—H12C109.5
C1iv—C1—C2122.90 (10)H12B—C12—H12C109.5
C1iv—C1—C8121.21 (10)C14—C13—C10120.53 (18)
C8—C1—C2115.88 (16)C14—C13—C17116.74 (19)
C3—C2—C1120.37 (17)C17—C13—C10122.64 (19)
C3—C2—C7118.45 (17)C13—C14—H14120.2
C7—C2—C1121.14 (19)C15—C14—C13119.7 (2)
C2—C3—H3119.6C15—C14—H14120.2
C2—C3—C4120.8 (2)N1—C15—C14123.8 (2)
C4—C3—H3119.6N1—C15—H15118.1
C3—C4—H4119.9C14—C15—H15118.1
C5—C4—C3120.2 (2)N1—C16—H16118.1
C5—C4—H4119.9N1—C16—C17123.8 (2)
C4—C5—H5120.2C17—C16—H16118.1
C6—C5—C4119.61 (19)C13—C17—H17120.2
C6—C5—H5120.2C16—C17—C13119.6 (2)
C5—C6—H6119.7C16—C17—H17120.2
Co1—N1—C15—C14178.9 (3)C7—C2—C3—C41.5 (3)
Co1—N1—C16—C17178.7 (2)C8—C1—C2—C344.7 (2)
S1—C10—C13—C14173.2 (2)C8—C1—C2—C7132.92 (18)
S1—C10—C13—C173.1 (3)C8—C9—C10—S10.7 (2)
N1—C16—C17—C130.4 (4)C8—C9—C10—C13175.4 (2)
C1iv—C1—C2—C3134.1 (2)C9—C8—C11—S11.8 (2)
C1iv—C1—C2—C748.3 (3)C9—C8—C11—C12177.0 (2)
C1iv—C1—C8—C949.7 (3)C9—C10—C13—C142.6 (4)
C1iv—C1—C8—C11131.5 (2)C9—C10—C13—C17178.9 (2)
C1—C2—C3—C4179.15 (17)C10—S1—C11—C81.90 (17)
C1—C2—C7—C6178.47 (16)C10—S1—C11—C12177.06 (19)
C1—C8—C9—C10179.59 (18)C10—C13—C14—C15176.1 (3)
C1—C8—C11—S1179.31 (15)C10—C13—C17—C16176.2 (2)
C1—C8—C11—C121.9 (4)C11—S1—C10—C91.48 (17)
C2—C1—C8—C9129.11 (19)C11—S1—C10—C13175.00 (18)
C2—C1—C8—C1149.7 (3)C11—C8—C9—C100.7 (3)
C2—C3—C4—C51.3 (3)C13—C14—C15—N10.0 (5)
C3—C2—C7—C60.8 (3)C14—C13—C17—C160.2 (4)
C3—C4—C5—C60.4 (3)C15—N1—C16—C170.7 (5)
C4—C5—C6—C70.2 (3)C16—N1—C15—C140.5 (5)
C5—C6—C7—C20.0 (3)C17—C13—C14—C150.4 (4)
Symmetry codes: (i) x+5/4, y+1/4, z; (ii) x+5/4, y, z+5/4; (iii) x, y+1/4, z+5/4; (iv) x+7/4, y+3/4, z.
(dte-8) top
Crystal data top
C68H56N4NiO2S4Dx = 1.067 Mg m3
Mr = 1148.11Synchrotron radiation, λ = 0.41328 Å
Orthorhombic, FdddCell parameters from 9920 reflections
a = 9.8621 (6) Åθ = 2.4–16.5°
b = 21.6164 (13) ŵ = 0.11 mm1
c = 67.069 (4) ÅT = 100 K
V = 14298.1 (15) Å3Prism, green
Z = 80.04 × 0.02 × 0.02 mm
F(000) = 4800
Data collection top
PILATUS3 1M
diffractometer
2604 reflections with I > 2σ(I)
φ and ω scansRint = 0.060
Absorption correction: multi-scan
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0730 before and 0.0572 after correction. The Ratio of minimum to maximum transmission is 0.9125. The λ/2 correction factor is Not present.
θmax = 14.1°, θmin = 1.3°
Tmin = 0.679, Tmax = 0.744h = 1111
71940 measured reflectionsk = 2424
3003 independent reflectionsl = 7878
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.101 w = 1/[σ2(Fo2) + (0.0406P)2 + 34.8474P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.003
3003 reflectionsΔρmax = 0.24 e Å3
182 parametersΔρmin = 0.35 e Å3
0 restraints
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)
Ni10.6250000.6250000.6250000.04067 (18)
S10.69450 (6)0.36619 (3)0.55243 (2)0.04071 (17)
O10.8373 (3)0.6250000.6250000.0516 (6)
H1A0.8944040.5982820.6185390.077*0.5
H1B0.8944040.6517280.6314610.077*0.5
N10.6147 (2)0.55723 (8)0.60271 (2)0.0427 (5)
C10.4434 (2)0.37571 (8)0.50540 (3)0.0304 (4)
C20.5265 (2)0.37187 (9)0.48673 (3)0.0313 (4)
C30.6345 (2)0.41236 (10)0.48373 (3)0.0374 (5)
H30.6543220.4428900.4934970.045*
C40.7138 (2)0.40856 (11)0.46660 (3)0.0429 (5)
H40.7866640.4366690.4646950.051*
C50.6866 (2)0.36392 (11)0.45232 (3)0.0448 (6)
H50.7405500.3614190.4406140.054*
C60.5810 (2)0.32320 (11)0.45521 (3)0.0425 (6)
H60.5626570.2923850.4454830.051*
C70.5012 (2)0.32680 (10)0.47225 (3)0.0361 (5)
H70.4287590.2983790.4740650.043*
C80.5217 (2)0.38195 (9)0.52441 (3)0.0297 (4)
C90.4959 (2)0.42861 (9)0.53887 (3)0.0304 (4)
H90.4258320.4584810.5375060.036*
C100.5814 (2)0.42645 (9)0.55492 (3)0.0333 (5)
C110.6289 (2)0.34549 (10)0.52962 (3)0.0359 (5)
C120.6935 (3)0.29337 (11)0.51819 (3)0.0466 (6)
H12A0.7399740.2655570.5274850.070*
H12B0.7592620.3102490.5086750.070*
H12C0.6234330.2703660.5109540.070*
C130.5909 (2)0.46964 (9)0.57174 (3)0.0357 (5)
C140.5086 (3)0.52164 (11)0.57268 (3)0.0470 (6)
H140.4417500.5282770.5627100.056*
C150.5231 (3)0.56346 (11)0.58788 (3)0.0517 (7)
H150.4656770.5987400.5879950.062*
C160.6937 (3)0.50695 (11)0.60192 (3)0.0456 (6)
H160.7590810.5013500.6121540.055*
C170.6857 (3)0.46272 (10)0.58710 (3)0.0434 (5)
H170.7442540.4278210.5873330.052*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0749 (4)0.0320 (3)0.0152 (3)0.0000.0000.000
S10.0508 (4)0.0410 (3)0.0303 (3)0.0145 (2)0.0087 (2)0.0056 (2)
O10.0743 (17)0.0511 (14)0.0296 (11)0.0000.0000.0008 (10)
N10.0746 (14)0.0342 (10)0.0193 (8)0.0059 (9)0.0073 (8)0.0001 (7)
C10.0473 (11)0.0226 (10)0.0212 (9)0.0067 (9)0.0000 (8)0.0005 (7)
C20.0433 (12)0.0285 (10)0.0220 (9)0.0111 (8)0.0001 (8)0.0010 (7)
C30.0476 (13)0.0349 (11)0.0295 (10)0.0062 (9)0.0029 (9)0.0004 (8)
C40.0466 (13)0.0466 (14)0.0354 (11)0.0069 (10)0.0072 (10)0.0068 (9)
C50.0518 (14)0.0574 (15)0.0250 (10)0.0202 (12)0.0038 (10)0.0032 (9)
C60.0541 (14)0.0497 (14)0.0236 (10)0.0204 (11)0.0054 (9)0.0074 (9)
C70.0470 (13)0.0360 (11)0.0252 (10)0.0104 (9)0.0032 (9)0.0024 (8)
C80.0411 (11)0.0276 (10)0.0202 (9)0.0028 (8)0.0018 (8)0.0009 (7)
C90.0440 (12)0.0255 (10)0.0216 (9)0.0052 (8)0.0003 (8)0.0010 (7)
C100.0472 (12)0.0308 (11)0.0219 (9)0.0045 (9)0.0006 (8)0.0013 (7)
C110.0445 (12)0.0352 (11)0.0279 (10)0.0071 (9)0.0028 (9)0.0044 (8)
C120.0597 (15)0.0399 (13)0.0401 (12)0.0202 (11)0.0073 (11)0.0085 (10)
C130.0543 (14)0.0320 (11)0.0207 (9)0.0025 (9)0.0026 (9)0.0005 (8)
C140.0694 (16)0.0457 (13)0.0258 (10)0.0174 (11)0.0139 (10)0.0068 (9)
C150.0872 (19)0.0425 (13)0.0254 (11)0.0236 (13)0.0109 (11)0.0055 (9)
C160.0695 (16)0.0429 (13)0.0243 (10)0.0098 (12)0.0117 (10)0.0013 (9)
C170.0666 (15)0.0369 (12)0.0266 (11)0.0121 (11)0.0085 (10)0.0019 (8)
Geometric parameters (Å, º) top
Ni1—O1i2.093 (3)C5—C61.377 (4)
Ni1—O12.093 (3)C6—H60.9500
Ni1—N12.0955 (17)C6—C71.390 (3)
Ni1—N1ii2.0957 (17)C7—H70.9500
Ni1—N1iii2.0957 (17)C8—C91.422 (3)
Ni1—N1i2.0957 (17)C8—C111.364 (3)
S1—C101.723 (2)C9—H90.9500
S1—C111.721 (2)C9—C101.369 (3)
O1—H1A0.9159C10—C131.467 (3)
O1—H1B0.9160C11—C121.504 (3)
N1—C151.350 (3)C12—H12A0.9800
N1—C161.338 (3)C12—H12B0.9800
C1—C1iv1.349 (4)C12—H12C0.9800
C1—C21.499 (3)C13—C141.388 (3)
C1—C81.497 (3)C13—C171.399 (3)
C2—C31.393 (3)C14—H140.9500
C2—C71.398 (3)C14—C151.370 (3)
C3—H30.9500C15—H150.9500
C3—C41.392 (3)C16—H160.9500
C4—H40.9500C16—C171.382 (3)
C4—C51.386 (3)C17—H170.9500
C5—H50.9500
O1i—Ni1—O1180.0C5—C6—C7120.6 (2)
O1i—Ni1—N1ii87.21 (6)C7—C6—H6119.7
O1—Ni1—N1i87.21 (6)C2—C7—H7119.7
O1—Ni1—N1iii87.21 (6)C6—C7—C2120.6 (2)
O1i—Ni1—N187.21 (6)C6—C7—H7119.7
O1—Ni1—N1ii92.79 (6)C9—C8—C1123.51 (17)
O1—Ni1—N192.79 (6)C11—C8—C1124.48 (17)
O1i—Ni1—N1iii92.79 (6)C11—C8—C9111.97 (17)
O1i—Ni1—N1i92.79 (6)C8—C9—H9123.2
N1i—Ni1—N1iii174.42 (12)C10—C9—C8113.69 (18)
N1ii—Ni1—N1i91.29 (9)C10—C9—H9123.2
N1ii—Ni1—N1iii88.98 (9)C9—C10—S1110.40 (14)
N1—Ni1—N1ii174.42 (12)C9—C10—C13128.50 (19)
N1—Ni1—N1iii91.29 (9)C13—C10—S1120.95 (16)
N1—Ni1—N1i88.98 (9)C8—C11—S1111.66 (15)
C11—S1—C1092.25 (10)C8—C11—C12129.10 (19)
Ni1—O1—H1A128.0C12—C11—S1119.24 (16)
Ni1—O1—H1B128.0C11—C12—H12A109.5
H1A—O1—H1B104.1C11—C12—H12B109.5
C15—N1—Ni1119.22 (15)C11—C12—H12C109.5
C16—N1—Ni1124.60 (14)H12A—C12—H12B109.5
C16—N1—C15116.17 (18)H12A—C12—H12C109.5
C1iv—C1—C2123.04 (11)H12B—C12—H12C109.5
C1iv—C1—C8121.21 (11)C14—C13—C10120.86 (18)
C8—C1—C2115.75 (17)C14—C13—C17116.36 (19)
C3—C2—C1120.23 (17)C17—C13—C10122.72 (19)
C3—C2—C7118.30 (18)C13—C14—H14119.8
C7—C2—C1121.44 (19)C15—C14—C13120.5 (2)
C2—C3—H3119.6C15—C14—H14119.8
C4—C3—C2120.7 (2)N1—C15—C14123.5 (2)
C4—C3—H3119.6N1—C15—H15118.2
C3—C4—H4119.9C14—C15—H15118.2
C5—C4—C3120.2 (2)N1—C16—H16118.0
C5—C4—H4119.9N1—C16—C17123.9 (2)
C4—C5—H5120.2C17—C16—H16118.0
C6—C5—C4119.6 (2)C13—C17—H17120.2
C6—C5—H5120.2C16—C17—C13119.6 (2)
C5—C6—H6119.7C16—C17—H17120.2
Ni1—N1—C15—C14179.9 (2)C7—C2—C3—C41.0 (3)
Ni1—N1—C16—C17179.90 (19)C8—C1—C2—C345.3 (2)
S1—C10—C13—C14173.51 (18)C8—C1—C2—C7132.57 (19)
S1—C10—C13—C173.6 (3)C8—C9—C10—S10.4 (2)
N1—C16—C17—C130.3 (4)C8—C9—C10—C13175.0 (2)
C1iv—C1—C2—C3134.1 (3)C9—C8—C11—S12.0 (2)
C1iv—C1—C2—C748.0 (3)C9—C8—C11—C12176.7 (2)
C1iv—C1—C8—C951.0 (3)C9—C10—C13—C141.4 (4)
C1iv—C1—C8—C11131.6 (3)C9—C10—C13—C17178.6 (2)
C1—C2—C3—C4178.94 (18)C10—S1—C11—C81.95 (18)
C1—C2—C7—C6178.71 (18)C10—S1—C11—C12176.94 (19)
C1—C8—C9—C10178.77 (18)C10—C13—C14—C15176.5 (2)
C1—C8—C11—S1179.73 (16)C10—C13—C17—C16176.6 (2)
C1—C8—C11—C121.0 (4)C11—S1—C10—C91.33 (17)
C2—C1—C8—C9128.5 (2)C11—S1—C10—C13174.45 (18)
C2—C1—C8—C1149.0 (3)C11—C8—C9—C101.1 (3)
C2—C3—C4—C50.5 (3)C13—C14—C15—N10.6 (4)
C3—C2—C7—C60.8 (3)C14—C13—C17—C160.6 (3)
C3—C4—C5—C60.2 (3)C15—N1—C16—C170.0 (4)
C4—C5—C6—C70.4 (3)C16—N1—C15—C140.2 (4)
C5—C6—C7—C20.1 (3)C17—C13—C14—C150.8 (4)
Symmetry codes: (i) x+5/4, y+5/4, z; (ii) x, y+5/4, z+5/4; (iii) x+5/4, y, z+5/4; (iv) x+3/4, y+3/4, z.
(dte-9) top
Crystal data top
C68H56N4O2S4Zn·2(NO3)Dx = 1.193 Mg m3
Mr = 1278.79Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, FdddCell parameters from 9836 reflections
a = 9.8296 (5) Åθ = 2.3–29.9°
b = 21.4844 (12) ŵ = 0.52 mm1
c = 67.400 (4) ÅT = 90 K
V = 14233.7 (13) Å3Prism, colourless
Z = 80.16 × 0.16 × 0.02 mm
F(000) = 5312
Data collection top
Bruker APEX-II CCD
diffractometer
4767 reflections with I > 2σ(I)
φ and ω scansRint = 0.048
Absorption correction: multi-scan
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1353 before and 0.0536 after correction. The Ratio of minimum to maximum transmission is 0.8796. The λ/2 correction factor is Not present.
θmax = 30.6°, θmin = 2.0°
Tmin = 0.656, Tmax = 0.746h = 1314
47600 measured reflectionsk = 3030
5466 independent reflectionsl = 9675
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.086H-atom parameters constrained
wR(F2) = 0.227 w = 1/[σ2(Fo2) + (0.0791P)2 + 179.9462P]
where P = (Fo2 + 2Fc2)/3
S = 1.21(Δ/σ)max = 0.001
5466 reflectionsΔρmax = 1.09 e Å3
243 parametersΔρmin = 0.50 e Å3
86 restraints
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)
Zn10.6250000.6250000.6250000.0291 (2)
S10.69323 (9)0.36467 (4)0.55203 (2)0.0246 (2)
O10.8446 (5)0.6250000.6250000.0403 (10)
H1A0.8888730.6514730.6146280.060*0.5
H1B0.8888730.5845280.6214730.060*0.5
N10.6128 (4)0.55515 (14)0.60233 (4)0.0318 (7)
C10.4440 (3)0.37558 (14)0.50519 (4)0.0165 (5)
C20.5269 (3)0.37173 (14)0.48664 (4)0.0183 (6)
C30.6350 (3)0.41246 (16)0.48369 (5)0.0238 (6)
H30.6552700.4430940.4934160.029*
C40.7136 (4)0.40860 (18)0.46660 (5)0.0285 (7)
H40.7866040.4368940.4646390.034*
C50.6857 (4)0.36339 (19)0.45232 (5)0.0307 (8)
H50.7397190.3606810.4406550.037*
C60.5801 (4)0.32299 (18)0.45524 (5)0.0288 (8)
H60.5610270.2921990.4455140.035*
C70.5001 (3)0.32634 (16)0.47227 (5)0.0223 (6)
H70.4274270.2977920.4741230.027*
C80.5216 (3)0.38186 (14)0.52409 (4)0.0170 (5)
C90.4945 (3)0.42826 (14)0.53851 (4)0.0164 (5)
H90.4240840.4582740.5371810.020*
C100.5802 (3)0.42551 (14)0.55463 (4)0.0182 (5)
C110.6288 (3)0.34465 (15)0.52929 (4)0.0218 (6)
C120.6932 (4)0.29264 (18)0.51781 (5)0.0318 (8)
H12A0.7616670.3096940.5087400.048*
H12B0.6232680.2707170.5101550.048*
H12C0.7368090.2635250.5270170.048*
C130.5894 (3)0.46829 (15)0.57147 (4)0.0202 (6)
C140.5054 (4)0.52045 (18)0.57239 (5)0.0313 (8)
H140.4385400.5273120.5624510.038*
C150.5201 (5)0.56204 (18)0.58781 (5)0.0370 (10)
H150.4619530.5973230.5882050.044*
C160.6924 (4)0.50497 (17)0.60165 (5)0.0305 (8)
H160.7580850.4994200.6118420.037*
C170.6841 (4)0.46034 (16)0.58673 (5)0.0280 (7)
H170.7420180.4249390.5869190.034*
N21.0701 (7)0.5278 (4)0.59290 (12)0.060 (3)0.335 (6)
O21.0161 (9)0.5791 (4)0.59596 (15)0.040 (3)0.335 (6)
O31.0170 (13)0.4793 (5)0.5998 (2)0.093 (5)0.335 (6)
O41.1779 (11)0.5245 (5)0.5831 (2)0.089 (5)0.335 (6)
N2A1.1391 (17)0.5768 (9)0.6006 (2)0.131 (14)0.165 (6)
O2A1.0148 (17)0.5638 (15)0.6010 (4)0.084 (9)0.165 (6)
O3A1.224 (2)0.5413 (9)0.6085 (3)0.060 (6)0.165 (6)
O4A1.178 (2)0.6252 (10)0.5922 (3)0.086 (8)0.165 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0573 (6)0.0211 (4)0.0090 (3)0.0000.0000.000
S10.0237 (4)0.0293 (4)0.0208 (4)0.0144 (3)0.0074 (3)0.0050 (3)
O10.056 (3)0.039 (2)0.0257 (18)0.0000.0000.0051 (17)
N10.059 (2)0.0218 (13)0.0144 (11)0.0088 (14)0.0098 (13)0.0023 (10)
C10.0210 (14)0.0167 (12)0.0119 (11)0.0090 (10)0.0001 (10)0.0014 (10)
C20.0201 (13)0.0216 (13)0.0133 (11)0.0118 (11)0.0009 (10)0.0009 (10)
C30.0242 (15)0.0253 (15)0.0217 (14)0.0096 (12)0.0038 (12)0.0003 (12)
C40.0224 (16)0.0354 (18)0.0277 (16)0.0077 (13)0.0091 (13)0.0069 (14)
C50.0289 (17)0.044 (2)0.0187 (14)0.0211 (16)0.0064 (13)0.0051 (14)
C60.0317 (18)0.0395 (19)0.0153 (13)0.0198 (15)0.0033 (12)0.0055 (13)
C70.0222 (15)0.0269 (15)0.0179 (13)0.0129 (12)0.0026 (11)0.0045 (11)
C80.0195 (13)0.0172 (12)0.0144 (12)0.0070 (10)0.0008 (10)0.0010 (10)
C90.0177 (13)0.0184 (12)0.0130 (11)0.0073 (10)0.0014 (10)0.0010 (9)
C100.0220 (14)0.0193 (13)0.0132 (12)0.0060 (11)0.0011 (10)0.0002 (10)
C110.0222 (14)0.0262 (15)0.0171 (13)0.0110 (12)0.0046 (11)0.0043 (11)
C120.0359 (19)0.0334 (18)0.0260 (16)0.0242 (16)0.0084 (14)0.0108 (14)
C130.0277 (16)0.0223 (14)0.0107 (11)0.0045 (12)0.0025 (11)0.0002 (10)
C140.043 (2)0.0335 (18)0.0174 (14)0.0183 (16)0.0130 (14)0.0069 (13)
C150.061 (3)0.0301 (17)0.0203 (16)0.0198 (18)0.0122 (16)0.0073 (13)
C160.045 (2)0.0290 (16)0.0169 (14)0.0083 (15)0.0113 (14)0.0027 (12)
C170.0388 (19)0.0260 (15)0.0193 (14)0.0086 (14)0.0112 (14)0.0041 (12)
N20.046 (6)0.083 (7)0.051 (7)0.019 (5)0.007 (5)0.007 (5)
O20.034 (5)0.070 (6)0.017 (5)0.024 (4)0.000 (3)0.014 (4)
O30.070 (8)0.109 (8)0.100 (11)0.004 (6)0.010 (8)0.022 (7)
O40.066 (7)0.072 (8)0.128 (12)0.010 (6)0.045 (8)0.008 (8)
N2A0.077 (12)0.169 (19)0.15 (3)0.017 (12)0.004 (10)0.057 (19)
O2A0.071 (11)0.15 (2)0.031 (15)0.019 (12)0.013 (9)0.017 (14)
O3A0.053 (11)0.077 (14)0.052 (12)0.013 (9)0.005 (9)0.025 (9)
O4A0.087 (15)0.128 (16)0.042 (11)0.033 (13)0.033 (10)0.005 (11)
Geometric parameters (Å, º) top
Zn1—O1i2.158 (5)C7—H70.9500
Zn1—O12.158 (5)C8—C91.418 (4)
Zn1—N12.145 (3)C8—C111.368 (4)
Zn1—N1ii2.145 (3)C9—H90.9500
Zn1—N1i2.145 (3)C9—C101.376 (4)
Zn1—N1iii2.145 (3)C10—C131.463 (4)
S1—C101.724 (3)C11—C121.500 (4)
S1—C111.714 (3)C12—H12A0.9800
O1—H1A1.0010C12—H12B0.9800
O1—H1B1.0012C12—H12C0.9800
N1—C151.345 (5)C13—C141.393 (5)
N1—C161.333 (5)C13—C171.398 (4)
C1—C1iv1.356 (6)C14—H140.9500
C1—C21.494 (4)C14—C151.379 (5)
C1—C81.491 (4)C15—H150.9500
C2—C31.391 (5)C16—H160.9500
C2—C71.400 (4)C16—C171.392 (5)
C3—H30.9500C17—H170.9500
C3—C41.389 (5)N2—O21.2407
C4—H40.9500N2—O31.2538
C4—C51.395 (6)N2—O41.2511
C5—H50.9500N2A—O2A1.2530
C5—C61.367 (6)N2A—O3A1.2509
C6—H60.9500N2A—O4A1.2418
C6—C71.393 (5)
O1—Zn1—O1i180.0C6—C7—C2120.0 (3)
N1iii—Zn1—O193.21 (11)C6—C7—H7120.0
N1ii—Zn1—O1i93.21 (11)C9—C8—C1123.6 (2)
N1—Zn1—O1i86.78 (11)C11—C8—C1124.1 (3)
N1iii—Zn1—O1i86.79 (11)C11—C8—C9112.3 (3)
N1ii—Zn1—O186.79 (11)C8—C9—H9123.3
N1—Zn1—O193.22 (11)C10—C9—C8113.3 (3)
N1i—Zn1—O1i93.21 (11)C10—C9—H9123.3
N1i—Zn1—O186.79 (11)C9—C10—S1110.3 (2)
N1iii—Zn1—N1173.6 (2)C9—C10—C13128.5 (3)
N1ii—Zn1—N1i173.6 (2)C13—C10—S1121.0 (2)
N1iii—Zn1—N1ii89.14 (16)C8—C11—S1111.6 (2)
N1ii—Zn1—N191.22 (16)C8—C11—C12128.9 (3)
N1i—Zn1—N189.14 (16)C12—C11—S1119.5 (2)
N1iii—Zn1—N1i91.22 (16)C11—C12—H12A109.5
C11—S1—C1092.46 (15)C11—C12—H12B109.5
Zn1—O1—H1A115.8C11—C12—H12C109.5
Zn1—O1—H1B115.8H12A—C12—H12B109.5
H1A—O1—H1B97.9H12A—C12—H12C109.5
C15—N1—Zn1118.6 (2)H12B—C12—H12C109.5
C16—N1—Zn1123.8 (2)C14—C13—C10120.2 (3)
C16—N1—C15117.5 (3)C14—C13—C17117.4 (3)
C1iv—C1—C2122.96 (17)C17—C13—C10122.3 (3)
C1iv—C1—C8120.90 (16)C13—C14—H14120.2
C8—C1—C2116.1 (3)C15—C14—C13119.5 (3)
C3—C2—C1120.1 (3)C15—C14—H14120.2
C3—C2—C7118.9 (3)N1—C15—C14123.3 (3)
C7—C2—C1121.0 (3)N1—C15—H15118.4
C2—C3—H3119.8C14—C15—H15118.4
C4—C3—C2120.4 (3)N1—C16—H16118.4
C4—C3—H3119.8N1—C16—C17123.2 (3)
C3—C4—H4119.8C17—C16—H16118.4
C3—C4—C5120.3 (4)C13—C17—H17120.4
C5—C4—H4119.8C16—C17—C13119.1 (3)
C4—C5—H5120.3C16—C17—H17120.4
C6—C5—C4119.4 (3)O2—N2—O3119.9
C6—C5—H5120.3O2—N2—O4120.0
C5—C6—H6119.5O4—N2—O3120.1
C5—C6—C7121.0 (3)O3A—N2A—O2A120.1
C7—C6—H6119.5O4A—N2A—O2A119.8
C2—C7—H7120.0O4A—N2A—O3A120.0
Zn1—N1—C15—C14178.9 (4)C7—C2—C3—C41.0 (5)
Zn1—N1—C16—C17179.4 (3)C8—C1—C2—C345.3 (4)
S1—C10—C13—C14174.1 (3)C8—C1—C2—C7132.9 (3)
S1—C10—C13—C173.5 (5)C8—C9—C10—S10.8 (4)
N1—C16—C17—C130.9 (6)C8—C9—C10—C13174.8 (3)
C1iv—C1—C2—C3133.8 (4)C9—C8—C11—S11.7 (4)
C1iv—C1—C2—C748.0 (5)C9—C8—C11—C12176.9 (4)
C1iv—C1—C8—C950.0 (5)C9—C10—C13—C141.1 (6)
C1iv—C1—C8—C11131.5 (4)C9—C10—C13—C17178.7 (4)
C1—C2—C3—C4179.2 (3)C10—S1—C11—C81.9 (3)
C1—C2—C7—C6179.0 (3)C10—S1—C11—C12176.9 (3)
C1—C8—C9—C10179.2 (3)C10—C13—C14—C15176.6 (4)
C1—C8—C11—S1179.7 (2)C10—C13—C17—C16176.1 (3)
C1—C8—C11—C121.7 (6)C11—S1—C10—C91.5 (3)
C2—C1—C8—C9129.1 (3)C11—S1—C10—C13174.4 (3)
C2—C1—C8—C1149.4 (4)C11—C8—C9—C100.6 (4)
C2—C3—C4—C50.7 (5)C13—C14—C15—N10.1 (7)
C3—C2—C7—C60.8 (4)C14—C13—C17—C161.5 (6)
C3—C4—C5—C60.2 (5)C15—N1—C16—C170.3 (6)
C4—C5—C6—C70.1 (5)C16—N1—C15—C140.8 (7)
C5—C6—C7—C20.4 (5)C17—C13—C14—C151.1 (6)
Symmetry codes: (i) x+5/4, y+5/4, z; (ii) x+5/4, y, z+5/4; (iii) x, y+5/4, z+5/4; (iv) x+3/4, y+3/4, z.
(dte-10) top
Crystal data top
C68H56CdN4O2S4·2(NO3)Dx = 1.211 Mg m3
Mr = 1325.82Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, FdddCell parameters from 9035 reflections
a = 9.8116 (12) Åθ = 2.2–28.2°
b = 21.432 (3) ŵ = 0.47 mm1
c = 69.162 (8) ÅT = 90 K
V = 14543 (3) Å3Prism, colourless
Z = 80.14 × 0.14 × 0.02 mm
F(000) = 5456
Data collection top
Bruker APEX-II CCD
diffractometer
4453 reflections with I > 2σ(I)
φ and ω scansRint = 0.048
Absorption correction: multi-scan
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1205 before and 0.0583 after correction. The Ratio of minimum to maximum transmission is 0.9130. The λ/2 correction factor is Not present.
θmax = 28.3°, θmin = 2.0°
Tmin = 0.681, Tmax = 0.746h = 1313
66341 measured reflectionsk = 2828
4548 independent reflectionsl = 9292
Refinement top
Refinement on F2Primary atom site location: heavy-atom method
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.093H-atom parameters constrained
wR(F2) = 0.233 w = 1/[σ2(Fo2) + (0.0494P)2 + 496.5558P]
where P = (Fo2 + 2Fc2)/3
S = 1.27(Δ/σ)max < 0.001
4548 reflectionsΔρmax = 1.41 e Å3
220 parametersΔρmin = 0.86 e Å3
47 restraints
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)
Cd10.6250000.1250000.1250000.0289 (2)
S10.69287 (16)0.38556 (8)0.19940 (2)0.0385 (4)
O10.3879 (9)0.1250000.1250000.060 (2)
H1A0.3455100.1067030.1345000.091*0.5
H1B0.3454050.1123880.1146700.091*0.5
N10.6058 (6)0.1998 (2)0.14891 (6)0.0333 (12)
C10.4439 (4)0.3743 (2)0.24506 (6)0.0160 (8)
C20.5264 (5)0.3780 (2)0.26316 (7)0.0201 (9)
C30.6344 (6)0.3366 (3)0.26614 (9)0.0321 (12)
H30.6541960.3057230.2566780.038*
C40.7133 (7)0.3400 (3)0.28281 (10)0.0419 (17)
H40.7863980.3115930.2846850.050*
C50.6857 (7)0.3847 (4)0.29666 (9)0.0443 (18)
H50.7387630.3869120.3081260.053*
C60.5804 (7)0.4261 (3)0.29365 (8)0.0376 (16)
H60.5619380.4572640.3030590.045*
C70.5007 (6)0.4230 (3)0.27710 (7)0.0264 (11)
H70.4282710.4517950.2753130.032*
C80.5223 (5)0.3681 (2)0.22681 (7)0.0215 (10)
C90.4928 (5)0.3219 (2)0.21232 (6)0.0174 (9)
H90.4214010.2921550.2134810.021*
C100.5782 (5)0.3250 (2)0.19664 (7)0.0213 (10)
C110.6308 (6)0.4049 (3)0.22176 (8)0.0284 (12)
C120.6965 (7)0.4562 (3)0.23306 (9)0.0419 (17)
H12A0.7580080.4383070.2427470.063*
H12B0.6260610.4809760.2395540.063*
H12C0.7485310.4831170.2242860.063*
C130.5864 (5)0.2838 (2)0.17991 (7)0.0225 (10)
C140.4995 (7)0.2333 (3)0.17820 (9)0.0428 (18)
H140.4314260.2263950.1877260.051*
C150.5111 (9)0.1926 (3)0.16264 (9)0.053 (2)
H150.4496400.1584430.1617260.063*
C160.6890 (7)0.2480 (3)0.15051 (8)0.0346 (14)
H160.7573870.2533030.1409260.042*
C170.6822 (7)0.2909 (3)0.16533 (9)0.0377 (15)
H170.7431290.3253870.1655490.045*
O20.2336 (9)0.1657 (4)0.09506 (11)0.038 (2)0.5
O30.0886 (12)0.2175 (7)0.0788 (2)0.077 (4)0.5
O40.2339 (15)0.2642 (7)0.0966 (2)0.082 (4)0.5
N20.1828 (12)0.2153 (5)0.09059 (18)0.062 (3)0.5
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cd10.0568 (6)0.0216 (4)0.0083 (3)0.0000.0000.000
S10.0347 (8)0.0485 (9)0.0322 (7)0.0273 (7)0.0194 (6)0.0191 (6)
O10.056 (5)0.099 (7)0.027 (3)0.0000.0000.007 (4)
N10.050 (3)0.032 (2)0.0178 (19)0.009 (2)0.011 (2)0.0046 (18)
C10.011 (2)0.022 (2)0.0151 (19)0.0053 (17)0.0002 (16)0.0012 (17)
C20.020 (2)0.024 (2)0.0165 (19)0.0096 (19)0.0050 (18)0.0013 (18)
C30.027 (3)0.029 (3)0.039 (3)0.009 (2)0.016 (3)0.005 (2)
C40.036 (3)0.044 (4)0.046 (4)0.014 (3)0.026 (3)0.018 (3)
C50.041 (4)0.065 (5)0.027 (3)0.031 (3)0.014 (3)0.017 (3)
C60.039 (3)0.059 (4)0.015 (2)0.031 (3)0.005 (2)0.005 (2)
C70.023 (3)0.038 (3)0.019 (2)0.014 (2)0.008 (2)0.004 (2)
C80.021 (2)0.021 (2)0.023 (2)0.0045 (19)0.0016 (19)0.0060 (18)
C90.014 (2)0.022 (2)0.016 (2)0.0049 (17)0.0007 (17)0.0007 (17)
C100.020 (2)0.027 (2)0.017 (2)0.0083 (19)0.0031 (18)0.0033 (18)
C110.020 (2)0.040 (3)0.026 (2)0.014 (2)0.008 (2)0.011 (2)
C120.042 (4)0.049 (4)0.034 (3)0.033 (3)0.016 (3)0.022 (3)
C130.023 (2)0.027 (2)0.017 (2)0.004 (2)0.0017 (19)0.0034 (18)
C140.050 (4)0.053 (4)0.025 (3)0.033 (3)0.025 (3)0.016 (3)
C150.079 (6)0.049 (4)0.030 (3)0.040 (4)0.029 (3)0.018 (3)
C160.038 (3)0.040 (3)0.025 (3)0.014 (3)0.016 (2)0.011 (2)
C170.035 (3)0.046 (3)0.032 (3)0.021 (3)0.018 (3)0.019 (3)
O20.027 (4)0.065 (5)0.021 (4)0.010 (4)0.004 (3)0.018 (3)
O30.051 (6)0.094 (9)0.084 (8)0.008 (6)0.030 (6)0.016 (7)
O40.064 (8)0.092 (7)0.091 (9)0.001 (6)0.015 (7)0.004 (6)
N20.039 (6)0.082 (6)0.064 (7)0.005 (5)0.015 (5)0.015 (5)
Geometric parameters (Å, º) top
Cd1—O1i2.327 (9)C5—C61.377 (11)
Cd1—O12.327 (9)C6—H60.9500
Cd1—N12.311 (5)C6—C71.387 (8)
Cd1—N1ii2.311 (5)C7—H70.9500
Cd1—N1i2.311 (5)C8—C91.439 (6)
Cd1—N1iii2.311 (5)C8—C111.370 (7)
S1—C101.728 (5)C9—H90.9500
S1—C111.713 (5)C9—C101.372 (6)
O1—H1Aiii0.87 (8)C10—C131.458 (7)
O1—H1A0.8707C11—C121.496 (7)
O1—H1B0.8701C12—H12A0.9800
O1—H1Biii0.87 (8)C12—H12B0.9800
N1—C151.337 (8)C12—H12C0.9800
N1—C161.321 (8)C13—C141.383 (8)
C1—C1iv1.352 (9)C13—C171.387 (7)
C1—C21.493 (6)C14—H140.9500
C1—C81.484 (6)C14—C151.391 (8)
C2—C31.398 (8)C15—H150.9500
C2—C71.387 (7)C16—H160.9500
C3—H30.9500C16—C171.380 (8)
C3—C41.391 (8)C17—H170.9500
C4—H40.9500O2—N21.214 (10)
C4—C51.381 (11)O3—N21.235 (10)
C5—H50.9500O4—N21.235 (11)
O1i—Cd1—O1180.0C6—C5—H5120.4
N1iii—Cd1—O1i94.68 (15)C5—C6—H6119.5
N1iii—Cd1—O185.32 (15)C5—C6—C7121.1 (6)
N1—Cd1—O185.32 (15)C7—C6—H6119.5
N1—Cd1—O1i94.68 (15)C2—C7—C6120.3 (6)
N1ii—Cd1—O1i85.32 (15)C2—C7—H7119.8
N1ii—Cd1—O194.68 (15)C6—C7—H7119.8
N1i—Cd1—O194.68 (15)C9—C8—C1123.3 (4)
N1i—Cd1—O1i85.32 (15)C11—C8—C1124.6 (4)
N1iii—Cd1—N1170.6 (3)C11—C8—C9112.0 (4)
N1ii—Cd1—N1i170.6 (3)C8—C9—H9123.4
N1iii—Cd1—N1i92.2 (2)C10—C9—C8113.2 (4)
N1ii—Cd1—N192.2 (2)C10—C9—H9123.4
N1i—Cd1—N188.6 (2)C9—C10—S1110.4 (4)
N1iii—Cd1—N1ii88.6 (2)C9—C10—C13129.1 (5)
C11—S1—C1092.8 (2)C13—C10—S1120.4 (4)
Cd1—O1—H1Aiii119 (3)C8—C11—S1111.5 (4)
Cd1—O1—H1A118.5C8—C11—C12128.7 (5)
Cd1—O1—H1B118.6C12—C11—S1119.7 (4)
Cd1—O1—H1Biii119 (3)C11—C12—H12A109.5
H1A—O1—H1Aiii123.0C11—C12—H12B109.5
H1Aiii—O1—H1Biii104.5C11—C12—H12C109.5
H1A—O1—H1Biii44.9H12A—C12—H12B109.5
H1A—O1—H1B104.5H12A—C12—H12C109.5
H1B—O1—H1Aiii44.9H12B—C12—H12C109.5
H1B—O1—H1Biii122.8C14—C13—C10120.5 (5)
C15—N1—Cd1119.0 (4)C14—C13—C17116.2 (5)
C16—N1—Cd1123.5 (4)C17—C13—C10123.2 (5)
C16—N1—C15117.4 (5)C13—C14—H14119.8
C1iv—C1—C2122.7 (3)C13—C14—C15120.5 (5)
C1iv—C1—C8121.4 (3)C15—C14—H14119.8
C8—C1—C2115.9 (4)N1—C15—C14122.3 (6)
C3—C2—C1120.1 (5)N1—C15—H15118.9
C7—C2—C1121.5 (5)C14—C15—H15118.9
C7—C2—C3118.4 (5)N1—C16—H16118.2
C2—C3—H3119.7N1—C16—C17123.7 (5)
C4—C3—C2120.7 (6)C17—C16—H16118.2
C4—C3—H3119.7C13—C17—H17120.0
C3—C4—H4119.9C16—C17—C13120.0 (5)
C5—C4—C3120.2 (7)C16—C17—H17120.0
C5—C4—H4119.9O2—N2—O3120.6 (12)
C4—C5—H5120.4O2—N2—O4119.3 (11)
C6—C5—C4119.3 (5)O4—N2—O3119.8 (12)
Cd1—N1—C15—C14175.5 (7)C7—C2—C3—C40.7 (8)
Cd1—N1—C16—C17176.6 (6)C8—C1—C2—C345.7 (7)
S1—C10—C13—C14176.5 (5)C8—C1—C2—C7132.6 (5)
S1—C10—C13—C171.3 (8)C8—C9—C10—S11.1 (6)
N1—C16—C17—C131.8 (12)C8—C9—C10—C13175.1 (5)
C1iv—C1—C2—C3133.6 (7)C9—C8—C11—S12.0 (6)
C1iv—C1—C2—C748.0 (8)C9—C8—C11—C12177.5 (7)
C1iv—C1—C8—C948.7 (9)C9—C10—C13—C140.6 (9)
C1iv—C1—C8—C11131.7 (7)C9—C10—C13—C17177.2 (6)
C1—C2—C3—C4179.1 (5)C10—S1—C11—C82.3 (5)
C1—C2—C7—C6178.9 (5)C10—S1—C11—C12177.3 (6)
C1—C8—C9—C10179.8 (5)C10—C13—C14—C15177.4 (7)
C1—C8—C11—S1178.3 (4)C10—C13—C17—C16176.2 (6)
C1—C8—C11—C122.1 (11)C11—S1—C10—C91.9 (5)
C2—C1—C8—C9130.7 (5)C11—S1—C10—C13174.7 (5)
C2—C1—C8—C1148.9 (7)C11—C8—C9—C100.6 (7)
C2—C3—C4—C50.1 (9)C13—C14—C15—N10.6 (14)
C3—C2—C7—C60.5 (8)C14—C13—C17—C161.7 (10)
C3—C4—C5—C60.7 (9)C15—N1—C16—C170.7 (11)
C4—C5—C6—C70.9 (9)C16—N1—C15—C140.5 (13)
C5—C6—C7—C20.3 (8)C17—C13—C14—C150.5 (11)
Symmetry codes: (i) x+5/4, y+1/4, z; (ii) x+5/4, y, z+1/4; (iii) x, y+1/4, z+1/4; (iv) x+3/4, y+3/4, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O2iii0.871.852.709 (9)167
O1—H1B···O20.872.092.709 (9)128
Symmetry code: (iii) x, y+1/4, z+1/4.
(dte-11) top
Crystal data top
C34H26CuIN2S2·CH2Cl2Z = 2
Mr = 802.05F(000) = 800
Triclinic, P1Dx = 1.629 Mg m3
a = 9.496 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.032 (3) ÅCell parameters from 4741 reflections
c = 17.380 (5) Åθ = 2.2–26.4°
α = 86.772 (8)°µ = 1.93 mm1
β = 84.163 (9)°T = 90 K
γ = 83.443 (9)°Plate, yellow
V = 1634.7 (8) Å30.14 × 0.06 × 0.01 mm
Data collection top
Bruker APEX-II CCD
diffractometer
3988 reflections with I > 2σ(I)
φ and ω scansRint = 0.070
Absorption correction: multi-scan
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1372 before and 0.0661 after correction. The Ratio of minimum to maximum transmission is 0.7738. The λ/2 correction factor is Not present.
θmax = 24.7°, θmin = 2.1°
Tmin = 0.577, Tmax = 0.745h = 1111
15927 measured reflectionsk = 1111
5512 independent reflectionsl = 2020
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.139 w = 1/[σ2(Fo2) + (0.0674P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
5512 reflectionsΔρmax = 1.56 e Å3
392 parametersΔρmin = 0.99 e Å3
0 restraints
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
Cu10.41700 (9)0.12901 (8)0.50322 (5)0.0214 (2)
S10.62638 (19)0.49354 (18)0.82463 (11)0.0241 (4)
S20.03898 (18)0.63303 (17)0.81059 (11)0.0226 (4)
N10.4511 (6)0.2638 (6)0.5809 (3)0.0223 (14)
N20.2566 (6)0.8206 (6)0.5668 (3)0.0213 (13)
C10.4401 (7)0.8717 (6)0.8420 (4)0.0179 (15)
C20.5479 (7)0.9672 (6)0.8523 (4)0.0193 (16)
C30.6710 (7)0.9624 (7)0.8003 (4)0.0255 (17)
H30.6854090.8998010.7604710.031*
C40.7724 (8)1.0503 (7)0.8075 (5)0.0292 (18)
H40.8554061.0476670.7719160.035*
C50.7541 (8)1.1396 (7)0.8648 (4)0.0286 (18)
H50.8252751.1969810.8697040.034*
C60.6326 (8)1.1468 (8)0.9156 (4)0.0303 (18)
H60.6187601.2109150.9545990.036*
C70.5299 (8)1.0600 (7)0.9096 (4)0.0265 (17)
H70.4467371.0645140.9451040.032*
C80.4977 (7)0.7322 (7)0.8211 (4)0.0203 (16)
C90.4569 (7)0.6683 (7)0.7574 (4)0.0198 (16)
H90.3939380.7117810.7224250.024*
C100.5175 (7)0.5366 (6)0.7510 (4)0.0182 (15)
C110.5932 (7)0.6516 (7)0.8623 (4)0.0217 (16)
C120.6591 (8)0.6793 (8)0.9335 (4)0.037 (2)
H12A0.607 (4)0.655 (5)0.973 (2)0.056*
H12B0.667 (5)0.763 (4)0.9342 (16)0.056*