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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

Crystal structure of benzyl N′-[(1E,4E)-1,5-bis­­(4-meth­­oxy­phen­yl)penta-1,4-dien-3-yl­­idene]hydrazine-1-carbodi­thio­ate

aDepartment of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor Darul Ehsan, Malaysia, and bDepartment of Chemistry, College of Education for Women, University of Anbar, Iraq
*Correspondence e-mail: ibra@upm.edu.my

Edited by M. Weil, Vienna University of Technology, Austria (Received 28 August 2019; accepted 1 October 2019; online 3 October 2019)

In the title hydrazinecarbodi­thio­ate derivative, C27H26N2O2S2, the asymmetric unit is comprised of four mol­ecules (Z = 8 and Z′ = 4). The 4-meth­oxy­phenyl rings are slightly twisted away from their attached olefinic double bonds [torsion angles = 5.9 (4)–19.6 (4)°]. The azomethine double bond has an s-trans configuration relative to one of the C=C bonds and an s-cis configuration relative to the other [C=C—C= N = 147.4 (6)–175.7 (2) and 15.3 (3)–37.4 (7)°, respectively]. The torsion angles between the azomethine C=N double bond and hydrazine-1-carbodi­thio­ate moiety indicate only small deviations from planarity, with torsion angles ranging from 0.9 (3) to 6.9 (3)° and from 174.9 (3) to 179.7 (2)°, respectively. The benzyl ring and the methyl­enesulfanyl moiety are almost perpendicular to each other, as indicated by their torsion angles [range 93.7 (3)–114.6 (2)°]. In the crystal, mol­ecules are linked by C—H⋯O, N—H⋯S and C—H⋯π(ring) hydrogen-bonding inter­actions into a three-dimensional network. Structural details of related benzyl hydrazine-1-carbodi­thio­ate are surveyed and compared with those of the title compound.

1. Chemical context

S-benzyl and S-alkyl di­thio­carbaza­tes are inter­esting ligands in coordination chemistry because they can act as N,S-chelating agents because of the presence of soft sulfur and hard nitro­gen donor atoms (Takjoo et al., 2016[Takjoo, R., Hayatolgheibi, S. S. & Rudbari, A. (2016). Inorg. Chim. Acta, 447, 52-58.]). These types of ligands can form stable metal complexes with five-membered chelate rings, and with transition metals in different stable oxidation states (Centore et al., 2013[Centore, R., Takjoo, R., Capobianco, A. & Peluso, A. (2013). Inorg. Chim. Acta, 404, 29-33.]). Di­thio­carbazate Schiff bases and their metal complexes show a wide range of biological activities such as anti-malarial, anti-bacterial, anti-viral and anti-tumour (Low et al., 2016[Low, M. L., Maigre, L., Tahir, M. I. M., Tiekink, E. R. T., Dorlet, P., Guillot, R., Ravoof, T. B., Rosli, R., Pagès, J., Policar, C., Delsuc, N. & Crouse, K. A. (2016). Eur. J. Med. Chem. 120, 1-12.]; Nanjundan et al., 2016[Nanjundan, N., Narayanasamy, R., Geib, S., Velmurugan, K., Nandhakumar, R., Balakumaran, M. D. & Kalaichelvan, P. T. (2016). Polyhedron, 110, 203-220.]; Islam et al., 2016a[Islam, M. A.-A.-A.-A., Sheikh, M. C., Mumit, M. A., Miyatake, R., Alam, M. A. & Mondal, M. O. A. (2016a). J. Coord. Chem. 69, 3580-3592.]). S-benzyl­dithio­carbazate and S-alkyl­dithio­carbazate Schiff base derivatives formed with aromatic aldehydes and ketones as well as their metal complexes have attracted attention due to their cytotoxicity against many types of cancer cell lines (Yusof et al., 2016[Yusof, E. N. M., Jotani, M. M., Tiekink, E. R. T. & Ravoof, T. B. S. A. (2016). Acta Cryst. E72, 516-521.]; 2017a[Yusof, E. N. M., Tahir, M. I. M., Ravoof, T. B. S. A., Tan, S. L. & Tiekink, E. R. T. (2017a). Acta Cryst. E73, 543-549.],b[Yusof, E. N. M., Ravoof, T. B. S. A., Tahir, M. I. M., Jotani, M. M. & Tiekink, E. R. T. (2017b). Acta Cryst. E73, 397-402.]; Vijayan et al., 2015[Vijayan, P., Viswanathamurthi, P., Sugumar, P., Ponnuswamy, M. N., Balakumaran, M. D., Kalaichelvan, P. T., Velmurugan, K., Nandhakumar, R. & Butcher, R. J. (2015). Inorg. Chem. Front. 2, 620-639.]; Basha et al., 2012[Basha, M. T., Chartres, J. D., Pantarat, N., Akbar Ali, M., Mirza, A. H., Kalinowski, D. S., Richardson, D. R. & Bernhardt, P. V. (2012). Dalton Trans. 41, 6536-6548.]), whereby S-methyl and S-benzyl di­thio­carbazate Schiff bases with 2-acetyl­pyridine show better cytotoxicity against a breast cancer cell line (MDA-MB-231) than their transition-metal complexes (Hamid et al., 2016[Hamid, M. H. S. A., Said, A. N. A., Mirza, A. H., Karim, M. R., Arifuzzaman, M., Ali, M. A. & Bernhardt, P. V. (2016). Inorg. Chim. Acta, 453, 742-750.]). Furthermore, Schiff bases synthesized from the reaction of S-benzyl­dithio­carbazate and m-hy­droxy­aceto­phenone as well as their metal complexes exhibit moderate analgesic and good anti-inflammatory activities in comparison with standard drugs diclofenac sodium and indomethacin (Mahapatra et al., 2017[Mahapatra, D. K., Bharti, S. K. & Asati, V. (2017). Curr. Top. Med. Chem. 17, 3146-3169.]).

[Scheme 1]

Encouraged by previous findings on various properties of related Schiff base derivatives, we report herein the synthesis and structure determination of the title compound (I). Structural details of (I) are compared with other hydrazinecarbodi­thio­ates.

2. Structural commentary

The asymmetric unit of (I) consists of four mol­ecules, denoted as A, B, C and D. Orientational disorder of the 1,5-bis(phen­yl)penta-1,4-dien-3-ylidenyl amine moiety in mol­ecule B and of the phenyl­methyl moiety in mol­ecule D were observed. The mol­ecules are composed of a 1,5-bis­(4-meth­oxy­phen­yl)penta-1,4-dien-3-ylidenyl moiety, connected to a benzyl ring by a hydrazine-1-carbodi­thio­ate (–C=N—(NH)—(C=S)—S—C–) bridge (Fig. 1[link]). Conformational details of the 1,5-bis­(4-meth­oxy­phen­yl)penta-1,4-dien-3-ylidenyl moiety can be described by the torsion angles between the 4-meth­oxy moiety and the phenyl ring [τ1 (C2—C3—O1—C26); τ6 (C16—C15—O2—C27)], between the 4-meth­oxy­phenyl ring and the olefinic double bond [τ2 (C5—C6-C7—C8); τ5 (C17—C12—C11—C10)], and between the olefinic double bond and the azomethine double bond [τ3 (N1—C9—C8—C7); τ4 (N1—C9—C10—C11)]. Torsion angles τ1 and τ6 are approximately 0° or ±180° in the majority of the four mol­ecules, except mol­ecule C which has a τ1 of 20.9 (3)° (Table 1[link]). The 4-meth­oxy­phenyl rings in the 1,5-bis­(4-meth­oxy­phen­yl)penta-1,4-dien-3-ylidenyl moiety are twisted away from their attached olefinic double bonds [τ2 = 5.9 (4)–16.4 (13)°; τ5 = 7.5 (3)–19.6 (4)°]. The orientations of the the azomethine double bond with its neighbouring olefinic double bonds relative to the inter­mediate C—C bond (C8—C9; C9—C10) are different: one is in s-trans [τ3 = 147.4 (6)–175.7 (2)°] conformation and the other in s-cis [τ4 = 15.3 (3)–37.4 (7)°] conformation. The dihedral angles between two 4-meth­oxy­phenyl rings in an individual mol­ecule are in the range 23.59 (12)–89.6 (5)° (Table 2[link]). Conformational details of the benzyl hydrazine-1-carbodi­thio­ate moiety can be outlined by torsion angles τ7 (C9—N1—N2—C18), τ8 (N1—N2—C18—S1), τ9 (N2—C18—S1—C19), τ10 (C18—S1—C19—C20) and τ11 (S1—C19—C20—C21). In all mol­ecules of (I), the hydrazine-1-carbo­thio­ate bridges are more or less planar (ideal values τ7, τ8 and τ9 = 0 or ±180°; experimental values: 0.9 (3)–6.9 (3)° and 174.9 (3)–179.7 (2)°, respectively). The torsion angles between the sulfane moiety and the methyl­ene moiety indicate a slight twist [τ10 = 160.53 (17)–163.36 (16)°]. These contortions are more severe between the benzyl ring and the methyl­ene sulfane moiety where τ11 is considerably smaller [τ11 = 93.7 (3)–114.6 (2)°]. The dihedral angles between the benzyl ring and the two 4-meth­oxy­phenyl rings are in the range 31.6 (5)–89.9 (8)° (Table 2[link]). An overlay of the four mol­ecules in the asymmetric unit was created with OLEX2 (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.]) and is shown in Fig. 2[link].

Table 1
Selected torsion angles (°) in the four mol­ecules of (I)

Torsion angles for the minor disorder component were omitted.

Mol­ecule τ A B C D
C2—C3—O1—C26 τ1 −2.8 (4) −7.3 (15) 20.9 (3) 5.0 (4)
C9—N1—N2—C18 τ7 −178.1 (2) −175.6 (4) −179.3 (2) 179.7 (2)
C5—C6—C7—C8 τ2 5.9 (4) 16.4 (13) 15.9 (4) −9.3 (4)
N1—N2—C18—S1 τ8 175.76 (16) −0.9 (3) 6.9 (3) 2.6 (3)
N1—C9—C8—C7 τ3 175.0 (2) 147.4 (6) −175.7 (2) −156.8 (2)
N2—C18—S1—C19 τ9 179.43 (17) −178.15 (17) −176.64 (17) −174.9 (3)
N1—C9—C10—C11 τ4 −37.5 (3) −37.4 (7) −26.9 (3) −15.3 (3)
S1—C19—C20—C21 τ10 160.53 (17) −160.75 (17) −163.36 (16) −162.9 (6)
C17—C12—C11—C10 τ5 19.6 (4) −18.4 (7) 7.5 (3) 15.9 (3)
S1—C19—C20—C21 τ11 −97.0 (2) 93.7 (3) −114.6 (2) −108.6 (12)
C16—C15—O2—C27 τ6 −0.9 (4) 4.1 (16) 177.5 (3) 177.9 (2)

Table 2
Selected dihedral angles (°)

Dihedral angle 1 is the dihedral angle between the mean planes of the 4-meth­oxy­phenyl rings; dihedral angle 2 is the dihedral angle between the mean planes of the benzyl (C20–C25) and 4-meth­oxy­phenyl (C1–C6) rings; dihedral angle 3 is the dihedral angle between the mean planes of the benzyl (C20–C25) and the 4-meth­oxy­phenyl (C12–C17) rings.

Mol­ecule Dihedral angle 1 Dihedral angle 2 Dihedral angle 3
A 56.72 (11) 85.02 (11) 72.11 (2)
B 89.6 (5) 31.6 (5) 64.9 (3)
C 23.59 (12) 84.46 (12) 86.00 (13)
D 60.82 (12) 36.6 (8) 89.9 (8)
[Figure 1]
Figure 1
The structures of the four independent mol­ecules in (I), showing 50% probability displacement ellipsoids and the atomic labelling scheme.
[Figure 2]
Figure 2
Overlay of the four mol­ecules in (I). The r.m.s deviation of A:B = 1.038 Å, A:C = 0.881 Å and A:D = 0.947 Å.

3. Supra­molecular features

In the crystal, mol­ecule A is inter­connected to mol­ecule B and mol­ecule C through weak C24A—H24A⋯O2B and C21A—H21A⋯O1C hydrogen-bonding inter­actions. Mol­ecules B and C each form inversion-related dimers via C21B—H21B⋯O1B and N2C—H3N2⋯S2C inter­actions, respectively (Fig. 3[link]a). In addition, mol­ecule C and mol­ecule D are connected through C17C—H17C⋯O1D hydrogen bonds (Fig. 3[link]b). The four mol­ecules are linked into an endless chain parallel to [021] through the combination of these hydrogen bonds (Fig. 4[link]). Further inter­actions, namely N2A—H1N2⋯S2A, N2B—H2N2⋯S2D and N2D—H4N2⋯S2B, link the chains into a three-dimensional network, as shown in Fig. 5[link]. Additional C—H⋯π inter­actions (Table 3[link]) consolidate the packing.

Table 3
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C12B–C17B, C12C–C17C and C1B–C6B rings, respectively.

D—H⋯A D—H H⋯A DA D—H⋯A
C24A—H24A⋯O2B 0.93 2.57 3.262 (3) 131
C21A—H21A⋯O1C 0.93 2.40 3.249 (3) 152
C21B—H21B⋯O1Bi 0.93 2.33 3.240 (4) 167
N2C—H3N2⋯S2Cii 0.91 (4) 2.53 (4) 3.435 (2) 179 (3)
C17C—H17C⋯O1Diii 0.93 2.53 3.381 (3) 152
N2A—H1N2⋯S2Aiv 0.81 (3) 2.69 (3) 3.473 (2) 161 (2)
N2B—H2N2⋯S2Dv 0.82 (3) 2.65 (3) 3.461 (2) 171 (3)
N2D—H4N2⋯S2Bv 0.91 (4) 2.61 (4) 3.517 (2) 174 (3)
C14C—H14CCg1iv 0.93 2.80 3.558 (5) 139
C16A—H16ACg2ii 0.93 2.80 3.680 (2) 158
C2D—H2DACg3 0.93 2.94 3.700 (5) 140
Symmetry codes: (i) -x, -y+2, -z; (ii) -x+2, -y, -z+1; (iii) -x+1, -y+1, -z+1; (iv) -x+1, -y, -z+1; (v) -x+1, -y+2, -z.
[Figure 3]
Figure 3
A partial packing diagram of the title compound, with N—H⋯S and C—H⋯O inter­actions (dotted lines). Hydrogen atoms not involved in these inter­actions were omitted for clarity.
[Figure 4]
Figure 4
A partial packing diagram of the title compound showing mol­ecules linked into chains by N—H⋯S and C—H⋯O inter­actions.
[Figure 5]
Figure 5
The overall packing of the title compound, viewed approximately along the a-axis direction.

4. Database survey

A search of the Cambridge Structural Database (CSD, version 5.40, last update May 2019; Groom et al., 2016[Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171-179.]) using benzyl 2-(λ2-methyl­ene)hydrazine-1-carbodi­thio­ate as reference moiety resulted in 45 structures with different substituents. The reference moiety and relevant torsion angles are illus­trated in Fig. 6[link]. Details regarding different substituents (R1) together with the torsion angles for the benzyl hydrazine-1-carbo­thio­ate moiety in these structures are collated in Table 4[link]. In analogy with the title mol­ecules, the planarity of the hydrazine-1-carbodi­thio­ate bridge for these structures is indicated by the τ7, τ8 and τ9; torsion angles τ7 and τ9 range from 165.1 to 180.0° and indicate an anti-periplanar conformation whereas torsion angle τ8 is indicative of a syn-periplanar conformation (0.0– 9.1°). With respect to torsion angle τ10, most of the structures adopt an anti-periplanar conformation ranging from 159.5 to 180.0°, but there are nine structures that adopt either a syn-clinal or an anti-clinal conformation (77.6–110.4°). In most of the structures, the benzyl ring and the methyl­ene sulfane moiety are orientated almost perpendicular to each other, as indicated by torsion angle τ11. Here, either a syn-clinal (68.1–88.4°) or an anti-clinal (92.2–141.1°) conformation is adopted. However, there is one outlier (WADGAK; Chan et al., 2003[Chan, M.-H. E., Crouse, K. A., Tarafder, M. T. H. & Yamin, B. M. (2003). Acta Cryst. E59, o628-o629.]) where the benzyl hydrazine-1-carbodi­thio­ate moiety is substituted with a 1-(thio­phen-2-yl)ethyl­idenyl moiety. In contrast to most of the structures, torsion angle τ11 = 17.1° for WADGAK indicates a syn-periplanar conformation.

Table 4
Torsion angles τ7, τ8, τ9, τ10 and τ11 (°) in related hydrazinecarbodi­thio­ates

Two sets of torsion angles are stated for compounds EXINAB, QORJAK, SIMMUX, VOJGUX and WUPGIX because there are two mol­ecules in their asymmetric units. The mol­ecule with disorder in the structure of compound ZENLIN was omitted from this table.

Compound R1 τ7 τ8 τ9 τ10 τ11
ABOROA (Manan et al., 2011[Manan, M. A. F. A., Crouse, K. A., Tahir, M. I. M., Rosli, R., How, F. N.-F., Watkin, D. J. & Slawin, A. M. Z. (2011). J. Chem. Crystallogr. 41, 1630-1641.]) 5-fluoro-2-oxo-1,2-di­hydro-3H-indol-3-yliden­yl 175.1 5.0 −176.8 168.2 −98.3
ABORUG (Manan et al., 2011[Manan, M. A. F. A., Crouse, K. A., Tahir, M. I. M., Rosli, R., How, F. N.-F., Watkin, D. J. & Slawin, A. M. Z. (2011). J. Chem. Crystallogr. 41, 1630-1641.]) 5-bromo-2-oxo-1,2-di­hydro-3H-indol-3-yliden­yl −178.5 −9.1 176.9 −108.0 −84.1
ABOSAN (Manan et al., 2011[Manan, M. A. F. A., Crouse, K. A., Tahir, M. I. M., Rosli, R., How, F. N.-F., Watkin, D. J. & Slawin, A. M. Z. (2011). J. Chem. Crystallogr. 41, 1630-1641.]) 5-chloro-2-oxo-1,2-di­hydro-3H-indol-3-yliden­yl −178.8 −7.7 177.5 −110.4 −81.8
BAHWIT (Md Yusof et al., 2015[Md Yusof, E. N., Ravoof, T. B. S. A., Tiekink, E. R. T., Veerakumarasivam, A., Crouse, K. A., Mohamed Tahir, M. I. & Ahmad, H. (2015). Int. J. Mol. Sci. 16, 11034-11054.]) 2-meth­oxy­benzyl­iden­yl −179.1 2.6 −178.0 −177.7 −85.7
BAHWOZ (Md Yusof et al., 2015[Md Yusof, E. N., Ravoof, T. B. S. A., Tiekink, E. R. T., Veerakumarasivam, A., Crouse, K. A., Mohamed Tahir, M. I. & Ahmad, H. (2015). Int. J. Mol. Sci. 16, 11034-11054.]) 3-meth­oxy­benzyl­iden­yl −178.0 −1.2 −178.1 173.8 −80.1
CEFBIB (Islam et al., 2016a[Islam, M. A.-A.-A.-A., Sheikh, M. C., Mumit, M. A., Miyatake, R., Alam, M. A. & Mondal, M. O. A. (2016a). J. Coord. Chem. 69, 3580-3592.]) 2,4,5-tri­meth­oxy­benzyl­iden­yl 179.6 −5.2 −177.9 173.4 −79.7
COBQUH (Mirza et al., 2014[Mirza, A. H., Hamid, M. H. S. A., Aripin, S., Karim, M. R., Arifuzzaman, M., Ali, M. A. & Bernhardt, P. V. (2014). Polyhedron, 74, 16-23.]) pyridin-2-yl­methylen­yl −177.2 −5.3 −177.2 −176.0 −68.7
DATFEK (Khoo et al., 2005[Khoo, T.-J., Cowley, A. R., Watkin, D. J., Crouse, K. A. & Tarafder, M. T. H. (2005). Acta Cryst. E61, o2441-o2443.]) furan-2-yl)ethyl­iden­yl 178.6 1.7 180.0 180.0 −72.5
EDETUD (How et al., 2007[How, F. N.-F., Watkin, D. J., Crouse, K. A. & Tahir, M. I. M. (2007). Acta Cryst. E63, o3023-o3024.]) 1-(3-pyrid­yl)ethyl­iden­yl −179.2 4.9 −179.8 −165.8 −87.5
EHIXUQ (Yusof et al., 2016[Yusof, E. N. M., Jotani, M. M., Tiekink, E. R. T. & Ravoof, T. B. S. A. (2016). Acta Cryst. E72, 516-521.]) 2-hy­droxy-3-meth­oxy­benzyl­iden­yl 177.4 1.8 179.9 −173.3 −101.2
EMEBAA (Ravoof et al., 2011[Ravoof, T. B. S. A., Crouse, K. A., Tahir, M. I. M., Rosli, R., Watkin, D. J. & How, F. N. F. (2011). J. Chem. Crystallogr. 41, 491-495.]) bis­(pyridin-2-yl)methylen­yl −165.7 1.4 175.4 176.2 −83.4
EPOFAR (Ali et al., 2011[Ali, M. A., Mirza, A. H., Bakar, H. J. H. A. & Bernhardt, P. V. (2011). Polyhedron, 30, 556-564.]) 2-oxo-1,2-di­hydro-3H-indol-3-yliden­yl 176.5 −4.5 −176.2 165.0 −95.5
EVITUZ (Shan et al., 2011a[Shan, S., Huang, Y.-L., Guo, H.-Q., Li, D.-F. & Sun, J. (2011a). Acta Cryst. E67, o2107.]) 2-nitro­benzyl­iden­yl 170.6 3.6 179.4 −80.1 132.1
EXINAB (Shan et al., 2011b[Shan, S., Wang, Z., Huang, Y.-L., Guo, H.-Q. & Li, D.-F. (2011b). Acta Cryst. E67, o2497.]) 2-methyl­benzyl­iden­yl −174.0 −176.9 −2.7 −4.9 −178.7 −177.4 174.2 175.6 −68.2 −68.7
GUMJUV (Break et al., 2013[Break, M. K., Tahir, M. I. M., Crouse, K. A. & Khoo, T.-J. (2013). Bioinorg. Chem. Appl. 2013, 362513.]) 4-chloro­phen­yl)ethyl­iden­yl −172.7 −0.3 −179.3 86.8 68.1
HELZIK (Omar et al., 2018[Omar, S. A., Chah, C. K., Ravoof, T. B. S. A., Jotani, M. M. & Tiekink, E. R. T. (2018). Acta Cryst. E74, 261-266.]) 1-(6-methyl­pyridin-2-yl)ethyl­iden­yl −177.7 −1.6 −176.0 171.6 −108.0
IFUTUZ (Khaledi et al., 2008a[Khaledi, H., Mohd Ali, H. & Ng, S. W. (2008a). Acta Cryst. E64, o2107.]) 1H-indol-3-yl­methyl­iden­yl −172.7 2.6 179.0 103.7 −68.2
JAMMOA (Ali et al., 2004[Ali, M. A., Mirza, A. H., Hamid, M. H. S. A., Bujang, F. H. & Bernhardt, P. V. (2004). Polyhedron, 23, 2405-2412.]) quinolinyl-2-methylen­yl 177.9 0.8 177.5 −171.0 101.8
KAGZOK (Ravoof et al., 2015[Ravoof, T. B. S. A., Tiekink, E. R. T., Omar, S. A., Begum, S. Z. & Tahir, M. I. M. (2015). Acta Cryst. E71, o1071-o1072.]) 1-(5-methyl­pyridin-2-yl)ethyl­iden­yl −176.9 −5.6 −173.2 164.7 −77.8
KUCRAC (Hamid et al., 2009[Hamid, M. H. S. A., Akbar Ali, M., Mirza, A. H., Bernhardt, P. V., Moubaraki, B. & Murray, K. S. (2009). Inorg. Chim. Acta, 362, 3648-3656.]) 1-(pyrazin-2-yl)ethyl­iden­yl 178.4 0.6 178.8 174.7 −70.0
KUCZUD (Xu et al., 1991[Xu, Z., Alyea, E. C., Ferguson, G. & Jennings, M. C. (1991). Polyhedron, 10, 1625-1629.]) pyridine-N-oxide-2-yl)methyl­iden­yl −171.4 −2.0 176.5 −161.7 −92.2
LOBSEB (Shan et al., 2008b[Shan, S., Tian, Y.-L., Wang, S.-H., Wang, W.-L. & Xu, Y.-L. (2008b). Acta Cryst. E64, o1024.]) furan-2-yl­methylen­yl 173.8 −0.5 179.7 177.1 −93.0
LOBVOO (Tarafder et al., 2008[Tarafder, M. T. H., Crouse, K. A., Islam, M. T., Chantrapromma, S. & Fun, H.-K. (2008). Acta Cryst. E64, o1042-o1043.]) (E)-3-phenyl­allyl­iden­yl −177.4 3.0 177.6 −175.3 −102.7
LOJBUI (Khaledi et al., 2008b[Khaledi, H., Mohd Ali, H. & Ng, S. W. (2008b). Acta Cryst. E64, o2430.]) 1-methyl-1H-indol-2-yl­methylen­yl 179.1 −2.3 −179.1 172.9 −78.9
LOJLIG (Khaledi et al., 2008b[Khaledi, H., Mohd Ali, H. & Ng, S. W. (2008b). Acta Cryst. E64, o2430.]) di­phenyl­methylen­yl 170.5 −1.2 −175.2 164.8 −83.8
LUBNIH (Zangrando et al., 2015[Zangrando, E., Islam, M. T., Islam, M. A.-A. A. A., Sheikh, M. C., Tarafder, M. T. H., Miyatake, R., Zahan, R. & Hossain, M. A. (2015). Inorg. Chim. Acta, 427, 278-284.]) 1-(3-hy­droxy­phen­yl)ethyl­iden­yl −177.5 −0.8 173.7 180.0 −71.1
NIZBUV (Omar et al., 2014[Omar, S. A., Ravoof, T. B. S. A., Tahir, M. I. M. & Crouse, K. A. (2014). Transition Met. Chem. 39, 119-126.]) 1-(4-methyl­pyridin-2-yl)ethyl­iden­yl −178.4 0.0 −175.8 −95.9 −141.1
OQOWOH (Akbar Ali et al., 2011[Akbar Ali, M., Mirza, A. H., Butcher, R. J., Bernhardt, P. V. & Karim, M. R. (2011). Polyhedron, 30, 1478-1486.]) bis­(pyridin-2-yl)methylen­yl 165.1 1.9 −177.2 −180.0 −83.8
PEWLEL (Li et al., 2012[Li, M. X., Zhang, L. Z., Chen, C. L., Niu, J. Y. & Ji, B. S. (2012). J. Inorg. Biochem. 106, 117-125.]) phen­yl(pyridin-2-yl)methylen­yl −177.0 4.6 −173.1 87.6 −119.2
QORJAK (Tan et al., 2015[Tan, Y.-F., Break, M. K., Tahir, M. I. M. bin & Khoo, T.-J. (2015). Acta Cryst. E71, 238-240.]) 3,4-di­meth­oxy­benzyl­iden­yl 169.2 −170.4 −3.1 3.7 −179.5 175.1 169.5 −168.8 −118.8 −105.7
QUCLIL (Biswal et al., 2015[Biswal, D., Pramanik, N. R., Chakrabarti, S., Chakraborty, N., Acharya, K., Mandal, S. S., Ghosh, S., Drew, M. G. B., Mondal, T. K. & Biswas, S. (2015). New J. Chem. 39, 2778-2794.]) 1-(2-hy­droxy­phen­yl)ethyl­idene2-hy­droxy­phen­yl)ethyl­iden­yl 176.7 0.6 −173.3 171.2 −115.5
RIYZOP (Shan et al., 2008a[Shan, S., Tian, Y.-L., Wang, S.-H., Wang, W.-L. & Xu, Y.-L. (2008a). Acta Cryst. E64, o1014.]) benzyl­iden­yl 177.1 0.1 178.5 171.8 −80.0
RUGLAH (Li et al., 2009[Li, H.-Q., Luo, Y., Qin, X. & Zhu, H.-L. (2009). Acta Cryst. E65, o3080.]) 3-nitro­benzyl­iden­yl 178.3 −2.9 −177.5 173.1 −85.5
SALSEE (Zhang et al., 2004[Zhang, M.-L., Tian, Y.-P., Zhang, X.-J., Wu, J.-Y., Zhang, S.-Y., Wang, D., Jiang, M.-H., Chantrapromm, S. & Fun, H.-K. (2004). Transition Met. Chem. 29, 596-602.]) 4-((2-hy­droxy­eth­yl)methyl­amino)­benzyl­iden­yl −166.4 0.9 −176.8 170.4 −88.4
SIMMUX (Qiu & Luo, 2007[Qiu, X.-Y. & Luo, Z.-G. (2007). Acta Cryst. E63, o4339.]) 2-bromo­benzyl­iden­yl 175.6 −173.9 2.6 −5.6 178.8 −176.3 −170.6 173.6 −115.6 75.2
TADVEC (Islam et al., 2016b[Islam, M. A. A. A. A., Sheikh, M. C., Mahmud, A. A., Miyatake, R. & Zangrando, E. (2016b). IUCrData, 1, x160190.]) 3,4,5-tri­meth­oxy­benzyl­iden­yl −179.4 −5.1 −177.1 174.9 −73.3
TIFSEH (Roy et al., 2007[Roy, S., Mandal, T. N., Barik, A. K., Pal, S., Gupta, S., Hazra, A., Butcher, R. J., Hunter, A. D., Zeller, M. & Kar, S. K. (2007). Polyhedron, 26, 2603-2611.]) 2-methyl­thio-6-methyl-4-pyrimid­yl)methylen­yl −177.8 0.6 −178.4 164.9 −76.6
UWATOD (Flörke & Boshaala, 2016[Flörke, U. & Boshaala, A. (2016). Private communication (refcode CCDC 1503552). CCDC, Cambridge, England.]) 1-phenyl­ethyl­iden­yl 172.4 −4.0 −173.3 159.5 −102.0
VOJCUT (Khaledi et al., 2008c[Khaledi, H., Mohd Ali, H. & Ng, S. W. (2008c). Acta Cryst. E64, o2482.]) 1-methyl-1H-indol-3-yl­methyl­iden­yl −177.2 −1.7 −176.0 −101.3 −129.4
VOJGUX (Shi et al., 2008[Shi, Z.-Q., Ji, N.-N. & Ji, Q.-Q. (2008). Acta Cryst. E64, o2249.]) 2-chloro­benzyl­iden­yl −174.7 178.3 −2.0 0.3 −179.3 176.9 −174.0 −174.1 −80.3 −110.1
WADGAK (Chan et al., 2003[Chan, M.-H. E., Crouse, K. A., Tarafder, M. T. H. & Yamin, B. M. (2003). Acta Cryst. E59, o628-o629.]) 1-(thio­phen-2-yl)ethyl­iden­yl 174.8 −5.8 177.8 77.6 17.1
WUPGIX (Tarafder et al., 2002[Tarafder, M. T. H., Khoo, T.-J., Crouse, K. A., Ali, A. M., Yamin, B. M. & Fun, H. K. (2002). Polyhedron, 21, 2691-2698.]) 5-methyl­furan-2-yl)methylen­yl −169.2 179.8 −0.2 1.5 179.7 −176.3 −173.6 −171.7 −100.8 −77.9
YAHDAO (Fan et al., 2011a[Fan, Z., Huang, Y.-L., Wang, Z., Guo, H.-Q. & Shan, S. (2011a). Acta Cryst. E67, o3011.]) 4-meth­oxy­benzyl­iden­yl −175.8 1.4 −179.5 −178.9 −87.9
YAHDUI (Fan et al., 2011b[Fan, Z., Huang, Y.-L., Wang, Z., Guo, H.-Q. & Shan, S. (2011b). Acta Cryst. E67, o3015.]) 2-bromo-5-meth­oxy­benzyl­iden­yl 177.8 −3.6 −176.0 174.9 119.2
ZENLIN (Fun et al., 1995[Fun, H.-K., Sivakumar, K., Yip, B.-C., Tian, Y.-P., Duan, C.-Y., Lu, Z.-L. & You, X.-Z. (1995). Acta Cryst. C51, 2080-2083.]) 4-(di­methyl­amino)­benzyl­iden­yl −180.0 1.3 179.9 −178.0 −97.1
[Figure 6]
Figure 6
General chemical scheme showing the definition of torsion angles, τ7, τ8, τ9, τ10 and τ11 in the benzyl hydrazine-1-carbo­thio­ate moiety.

5. Synthesis and crystallization

Compound (I) was synthesized following a well-described literature protocol (Ali & Tarafder, 1977[Ali, M. A. & Tarafder, M. T. H. (1977). J. Inorg. Nucl. Chem. 39, 1785-1791.]; Ravoof et al., 2010[Ravoof, T. B. S. A., Crouse, K. A., Tahir, M. I. M., How, F. N. F., Rosli, R. & Watkins, D. J. (2010). Transition Met. Chem. 35, 871-876.]; Omar et al., 2014[Omar, S. A., Ravoof, T. B. S. A., Tahir, M. I. M. & Crouse, K. A. (2014). Transition Met. Chem. 39, 119-126.]). S-benzyl­dithio­carbazate (1.98 g, 0.01 mol) was dissolved in absolute ethanol (50 ml) under heating and stirring. The resulting solution was slowly added to a hot solution of di-p-meth­oxy­benzalacetone (2.94 g, 0.01 mol) dissolved in absolute ethanol (50 ml). 3-5 drops of concentrated hydro­chloric acid were added to the mixture, which was subsequently heated and stirred for 5 h (Fig. 7[link]). The acidified mixture was allowed to stand overnight, resulting in the formation of red crystals. They were filtered off and recrystallized using the slow evaporation technique from absolute ethanol as solvent.

[Figure 7]
Figure 7
Reaction scheme for the synthesis of (I).

Yield: 57.3%. m.p.: 375-376 K. Analysis calculated for C27H26N2O2S2: C, 49.71; H, 5.52; N, 5.90; S, 13.51% found: C, 49.68; H, 5.48; N, 5.97; S, 13.55%. FT-IR (cm−1): 3145, ν(N—H); 1630, ν(C=N); 1244, ν(N—N); 1059, ν(C=S); 3145. 1H NMR (CDCl3) δ (p.p.m.)= 6.55–7.68 (aromatic H); 3.85 (OCH3); 4.55 (–CH2 benz­yl); 10.20 (N—H). 13C NMR (CDCl3) δ(p.p.m.)= 114.35–142.88 (aromatic C); 55.55 (OCH3); 39.34 (–CH2 benz­yl); 161.22 (C=N); 206.91 (C=S). m/z calculated for C27H26N2O2S2: 474, found 474.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 5[link]. The labelling of atoms is the same in each mol­ecule, with the mol­ecule indicated by the suffix A, B, C or D. The N-bound H atoms were located in difference-Fourier maps and were refined freely [N—H = 0.81 (3)–0.91 (4) Å]. The C-bound H atoms were positioned geometrically (C—H = 0.93–0.97 Å) and refined using a riding model, with Uiso(H) = 1.2 or 1.5Ueq(C). A rotating-group model was applied to the methyl groups. The 1,5-bis­(phen­yl)penta-1,4-dien-3-ylidenyl amine moiety in mol­ecule B and the phenyl­methyl moiety in mol­ecule D display positional disorder, with refined site occupancy ratios of 0.667 (7):0.333 (7) and 0.653 (15):0.347 (15), respectively (SIMU, DELU and SAME restraints were used).

Table 5
Experimental details

Crystal data
Chemical formula C27H26N2O2S2
Mr 474.62
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 100
a, b, c (Å) 10.2010 (1), 20.0260 (3), 25.2349 (4)
α, β, γ (°) 70.535 (1), 86.852 (1), 82.147 (1)
V3) 4814.65 (12)
Z 8
Radiation type Cu Kα
μ (mm−1) 2.22
Crystal size (mm) 0.14 × 0.08 × 0.05
 
Data collection
Diffractometer XtaLAB Synergy, Dualflex, AtlasS2
Absorption correction Gaussian (CrysAlis PRO; Rigaku OD, 2018[Rigaku OD (2018). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.])
Tmin, Tmax 0.681, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections 114750, 17182, 14177
Rint 0.046
(sin θ/λ)max−1) 0.597
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.130, 1.03
No. of reflections 17182
No. of parameters 1449
No. of restraints 80
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 1.16, −0.62
Computer programs: CrysAlis PRO (Rigaku OD, 2018[Rigaku OD (2018). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]), SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]), SHELXL2013 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]), OLEX2 (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.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2018); cell refinement: CrysAlis PRO (Rigaku OD, 2018); data reduction: CrysAlis PRO (Rigaku OD, 2018); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: SHELXL2013 (Sheldrick, 2015), Mercury (Macrae et al., 2006) and OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2015) and PLATON (Spek, 2009).

Benzyl N'-[(1E,4E)-1,5-bis(4-methoxyphenyl)penta-1,4-dien-3-ylidene]hydrazine-1-carbodithioate top
Crystal data top
C27H26N2O2S2Z = 8
Mr = 474.62F(000) = 2000
Triclinic, P1Dx = 1.310 Mg m3
a = 10.2010 (1) ÅCu Kα radiation, λ = 1.54178 Å
b = 20.0260 (3) ÅCell parameters from 39902 reflections
c = 25.2349 (4) Åθ = 3.7–76.4°
α = 70.535 (1)°µ = 2.22 mm1
β = 86.852 (1)°T = 100 K
γ = 82.147 (1)°Plate, clear intense red
V = 4814.65 (12) Å30.14 × 0.08 × 0.05 mm
Data collection top
XtaLAB Synergy, Dualflex, AtlasS2
diffractometer
17182 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source14177 reflections with I > 2σ(I)
Detector resolution: 5.2558 pixels mm-1Rint = 0.046
ω scansθmax = 67.1°, θmin = 3.5°
Absorption correction: gaussian
(CrysAlis PRO; Rigaku OD, 2018)
h = 1212
Tmin = 0.681, Tmax = 1.000k = 2322
114750 measured reflectionsl = 3030
Refinement top
Refinement on F280 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.048H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.130 w = 1/[σ2(Fo2) + (0.0653P)2 + 3.3132P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
17182 reflectionsΔρmax = 1.16 e Å3
1449 parametersΔρmin = 0.62 e Å3
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S1A0.38286 (5)0.22017 (3)0.45386 (2)0.02996 (13)
S2A0.33363 (5)0.06508 (3)0.50610 (2)0.02843 (12)
N1A0.59006 (18)0.16709 (9)0.40187 (8)0.0289 (4)
N2A0.52876 (18)0.11192 (10)0.43731 (8)0.0273 (4)
H1N20.553 (3)0.0696 (15)0.4436 (11)0.035 (7)*
O1A1.10882 (18)0.19587 (9)0.33832 (8)0.0455 (4)
O2A0.78919 (19)0.52640 (9)0.13693 (8)0.0502 (5)
C1A1.0517 (2)0.00371 (12)0.31844 (10)0.0327 (5)
H1AA1.0908140.0377420.3017840.039*
C2A1.1166 (2)0.06786 (13)0.31486 (11)0.0360 (5)
H2AA1.1974860.0692350.2961240.043*
C3A1.0584 (2)0.12966 (12)0.33974 (10)0.0344 (5)
C4A0.9379 (2)0.12664 (12)0.36779 (10)0.0354 (5)
H4AA0.8994500.1682730.3847490.043*
C5A0.8748 (2)0.06274 (12)0.37073 (10)0.0315 (5)
H5AA0.7937950.0615970.3894440.038*
C6A0.9311 (2)0.00086 (11)0.34583 (9)0.0275 (4)
C7A0.8665 (2)0.07035 (11)0.34688 (9)0.0283 (4)
H7AA0.9075140.1098910.3262130.034*
C8A0.7556 (2)0.08318 (11)0.37416 (9)0.0288 (4)
H8AA0.7148770.0440690.3959160.035*
C9A0.6929 (2)0.15396 (11)0.37257 (9)0.0281 (4)
C10A0.7424 (2)0.21836 (11)0.33310 (9)0.0299 (5)
H10A0.8332520.2187390.3276600.036*
C11A0.6612 (2)0.27617 (11)0.30489 (10)0.0326 (5)
H11A0.5712180.2749500.3126630.039*
C12A0.6996 (2)0.34134 (11)0.26292 (10)0.0320 (5)
C13A0.6064 (2)0.38630 (12)0.22410 (11)0.0375 (5)
H13A0.5201520.3752200.2264690.045*
C14A0.6390 (3)0.44668 (12)0.18239 (11)0.0404 (6)
H14A0.5755340.4752490.1566630.048*
C15A0.7669 (2)0.46478 (12)0.17885 (11)0.0379 (5)
C16A0.8617 (2)0.42146 (12)0.21703 (11)0.0375 (5)
H16A0.9474450.4331610.2148520.045*
C17A0.8274 (2)0.36054 (11)0.25847 (10)0.0337 (5)
H17A0.8911630.3317730.2839250.040*
C18A0.4203 (2)0.12795 (11)0.46564 (9)0.0264 (4)
C19A0.2365 (2)0.22242 (13)0.49776 (13)0.0448 (7)
H19A0.1598690.2176680.4787950.054*
H19B0.2473770.1829430.5328240.054*
C20A0.2159 (2)0.29220 (11)0.50951 (10)0.0309 (5)
C21A0.2611 (2)0.29552 (13)0.55912 (11)0.0399 (6)
H21A0.3075450.2550740.5840800.048*
C22A0.2387 (3)0.35777 (14)0.57229 (11)0.0419 (6)
H22A0.2687960.3588550.6060800.050*
C23A0.1716 (2)0.41825 (12)0.53528 (11)0.0371 (5)
H23A0.1563310.4602900.5439930.044*
C24A0.1273 (2)0.41627 (12)0.48555 (11)0.0387 (5)
H24A0.0825660.4572300.4604700.046*
C25A0.1486 (2)0.35363 (12)0.47231 (10)0.0342 (5)
H25A0.1178320.3527400.4385630.041*
C26A1.2328 (3)0.20308 (17)0.31144 (17)0.0622 (9)
H26A1.2578820.2521980.3145250.093*
H26B1.2982210.1875790.3290790.093*
H26C1.2263130.1743510.2724850.093*
C27A0.9199 (3)0.54696 (15)0.13175 (14)0.0591 (8)
H27A0.9237180.5895670.1000000.089*
H27B0.9826680.5092790.1265300.089*
H27C0.9407970.5557810.1652700.089*
S1B0.39730 (6)0.76943 (3)0.04835 (2)0.03568 (14)
S2B0.43703 (5)0.92506 (3)0.00786 (2)0.03000 (13)
N2B0.2514 (2)0.87613 (11)0.06618 (9)0.0382 (5)
H2N20.227 (3)0.9186 (15)0.0605 (12)0.035 (7)*
O1B0.31580 (19)1.19059 (12)0.15074 (8)0.0544 (5)
O2B0.05549 (17)0.47568 (8)0.37333 (7)0.0382 (4)
C18B0.3579 (2)0.86140 (11)0.03607 (9)0.0309 (5)
C19B0.5367 (2)0.76729 (12)0.00149 (13)0.0442 (6)
H19C0.5213370.8057290.0339590.053*
H19D0.6162360.7731250.0179780.053*
C20B0.5526 (2)0.69606 (12)0.00798 (11)0.0359 (5)
C21B0.4943 (3)0.68917 (15)0.05345 (12)0.0488 (6)
H21B0.4428170.7282940.0775430.059*
C22B0.5111 (3)0.62506 (18)0.06389 (13)0.0573 (8)
H22B0.4716490.6215750.0950640.069*
C23B0.5855 (3)0.56663 (15)0.02866 (13)0.0524 (7)
H23B0.5989080.5238440.0362920.063*
C24B0.6400 (3)0.57196 (13)0.01807 (12)0.0516 (7)
H24B0.6880220.5320360.0429230.062*
C25B0.6243 (3)0.63638 (13)0.02859 (12)0.0440 (6)
H25B0.6619560.6394340.0603010.053*
C26B0.3399 (3)1.21002 (18)0.20007 (13)0.0585 (8)
H26D0.3830611.2581730.1901060.088*
H26E0.2573781.2065760.2179220.088*
H26F0.3955551.1784030.2254700.088*
C27B0.1821 (3)0.45199 (14)0.37586 (12)0.0464 (6)
H27D0.1850340.4087260.4070670.070*
H27E0.1968370.4432620.3416290.070*
H27F0.2495140.4880440.3805910.070*
S1C1.11763 (6)0.22107 (3)0.54167 (2)0.03300 (13)
S2C1.13700 (7)0.06552 (3)0.47861 (3)0.04438 (16)
N1C0.92728 (19)0.16897 (9)0.60427 (8)0.0310 (4)
N2C0.96835 (19)0.11438 (10)0.56067 (8)0.0308 (4)
H3N20.941 (3)0.0668 (18)0.5497 (14)0.062 (9)*
O1C0.38467 (17)0.18373 (9)0.67618 (8)0.0424 (4)
O2C0.7281 (2)0.53080 (10)0.86542 (9)0.0595 (5)
C1C0.4978 (2)0.00762 (13)0.71071 (10)0.0383 (5)
H1CA0.4890650.0505670.7391300.046*
C2C0.4318 (2)0.05467 (13)0.71624 (10)0.0375 (5)
H2CA0.3803300.0534880.7480400.045*
C3C0.4429 (2)0.11881 (12)0.67410 (10)0.0324 (5)
C4C0.5178 (2)0.11903 (13)0.62654 (11)0.0402 (6)
H4CA0.5235310.1619300.5976300.048*
C5C0.5838 (2)0.05681 (12)0.62143 (10)0.0377 (5)
H5CA0.6336460.0581370.5891900.045*
C6C0.5768 (2)0.00852 (12)0.66427 (10)0.0316 (5)
C7C0.6511 (2)0.07643 (12)0.66400 (10)0.0339 (5)
H7CA0.6221820.1175030.6891930.041*
C8C0.7550 (2)0.08630 (11)0.63195 (9)0.0306 (5)
H8CA0.7821890.0462910.6046520.037*
C9C0.8293 (2)0.15577 (11)0.63682 (9)0.0297 (5)
C10C0.7988 (2)0.21889 (12)0.68407 (10)0.0318 (5)
H10C0.7604750.2112090.7161780.038*
C11C0.8219 (2)0.28565 (12)0.68419 (10)0.0319 (5)
H11C0.8562970.2927520.6513160.038*
C12C0.7979 (2)0.34955 (12)0.73162 (10)0.0321 (5)
C13C0.8149 (3)0.41598 (12)0.72411 (11)0.0399 (6)
H13C0.8418930.4190450.6891040.048*
C14C0.7926 (3)0.47799 (13)0.76760 (12)0.0451 (6)
H14C0.8038280.5217050.7614520.054*
C15C0.7540 (3)0.47420 (13)0.81963 (11)0.0430 (6)
C16C0.7396 (2)0.40854 (13)0.82858 (11)0.0411 (6)
H16C0.7156100.4060110.8640180.049*
C17C0.7607 (2)0.34747 (12)0.78525 (10)0.0343 (5)
H17C0.7500030.3039800.7917640.041*
C18C1.0683 (2)0.12894 (13)0.52717 (10)0.0342 (5)
C19C1.2426 (2)0.21912 (12)0.48679 (11)0.0356 (5)
H19E1.2115220.1840860.4514630.043*
H19F1.3235960.2059130.4966740.043*
C20C1.2686 (2)0.29216 (11)0.48084 (9)0.0304 (5)
C21C1.3916 (2)0.33277 (13)0.49416 (12)0.0403 (6)
H21C1.4576080.3152250.5077700.048*
C22C1.4165 (3)0.39910 (14)0.48731 (14)0.0518 (7)
H22C1.4989570.4259610.4964610.062*
C23C1.3198 (3)0.42546 (13)0.46702 (13)0.0470 (7)
H23C1.3370100.4699160.4622210.056*
C24C1.1982 (3)0.38611 (14)0.45391 (12)0.0437 (6)
H24C1.1328020.4041430.4403870.052*
C25C1.1717 (2)0.31965 (13)0.46060 (11)0.0378 (5)
H25C1.0887700.2933310.4515230.045*
C26C0.2749 (2)0.18433 (14)0.71364 (12)0.0421 (6)
H26G0.2357430.2326710.7075030.063*
H26H0.3046290.1632570.7517480.063*
H26I0.2103610.1574780.7068770.063*
C27C0.7472 (4)0.59989 (16)0.85860 (16)0.0765 (11)
H27G0.7204110.6348400.8924390.115*
H27H0.8389320.6120350.8510000.115*
H27I0.6948710.5989800.8278220.115*
S2D0.87082 (7)0.94461 (4)0.02823 (3)0.05084 (18)
N1D0.67804 (19)0.84475 (11)0.10430 (9)0.0368 (4)
N2D0.71944 (19)0.89845 (11)0.06061 (9)0.0353 (4)
H4N20.680 (3)0.9447 (19)0.0493 (15)0.066 (10)*
O1D0.17094 (18)1.21299 (9)0.17203 (9)0.0464 (4)
O2D0.4571 (2)0.49382 (9)0.36916 (8)0.0481 (4)
C1D0.2135 (2)1.02822 (12)0.17183 (11)0.0360 (5)
H1DA0.1656250.9897350.1791640.043*
C2D0.1496 (2)1.09145 (13)0.17662 (11)0.0389 (5)
H2DA0.0603801.0955860.1863670.047*
C3D0.2215 (2)1.14876 (12)0.16658 (10)0.0352 (5)
C4D0.3540 (2)1.14194 (13)0.15068 (11)0.0391 (6)
H4DA0.4018311.1804370.1435350.047*
C5D0.4150 (2)1.07893 (12)0.14542 (10)0.0359 (5)
H5DA0.5034121.0755580.1343040.043*
C6D0.3464 (2)1.01957 (12)0.15651 (9)0.0308 (5)
C7D0.4073 (2)0.95049 (11)0.15394 (9)0.0297 (5)
H7DA0.3561370.9131760.1675020.036*
C8D0.5280 (2)0.93413 (12)0.13443 (9)0.0311 (5)
H8DA0.5795070.9708720.1183850.037*
C9D0.5835 (2)0.86182 (12)0.13692 (10)0.0310 (5)
C10D0.5399 (2)0.80078 (12)0.18230 (10)0.0333 (5)
H10D0.4900360.8104120.2114850.040*
C11D0.5664 (2)0.73254 (12)0.18488 (10)0.0358 (5)
H11D0.6067740.7236340.1535440.043*
C12D0.5375 (2)0.67071 (12)0.23253 (10)0.0363 (5)
C13D0.5449 (3)0.60356 (14)0.22646 (12)0.0479 (6)
H13D0.5679370.5990020.1915400.058*
C14D0.5193 (3)0.54365 (14)0.27040 (12)0.0489 (7)
H14D0.5245880.4997380.2648070.059*
C15D0.4856 (3)0.54910 (13)0.32285 (11)0.0409 (6)
C16D0.4824 (2)0.61498 (13)0.33092 (11)0.0386 (5)
H16D0.4632800.6187900.3663410.046*
C17D0.5073 (2)0.67434 (12)0.28650 (11)0.0354 (5)
H17D0.5041160.7179480.2924320.043*
C18D0.8177 (2)0.88359 (15)0.02564 (13)0.0453 (6)
C26D0.0331 (3)1.22342 (15)0.18465 (15)0.0539 (7)
H26J0.0095611.2706760.1865040.081*
H26K0.0141101.1889810.2201610.081*
H26L0.0172031.2176100.1557630.081*
C27D0.4637 (3)0.42460 (14)0.36333 (13)0.0554 (7)
H27J0.4366680.3912420.3979910.083*
H27K0.5528030.4092050.3542910.083*
H27L0.4058680.4270300.3337900.083*
C1B0.1596 (13)1.0124 (6)0.2057 (4)0.029 (2)0.667 (7)
H1BA0.1393650.9767000.2398990.035*0.667 (7)
C2B0.2170 (17)1.0787 (6)0.2066 (4)0.030 (2)0.667 (7)
H2BA0.2310491.0880330.2403170.036*0.667 (7)
C3B0.2530 (12)1.1308 (4)0.1560 (3)0.0299 (19)0.667 (7)
C4B0.2285 (12)1.1158 (4)0.1058 (3)0.0291 (17)0.667 (7)
H4BA0.2530741.1509200.0718090.035*0.667 (7)
C5B0.1684 (9)1.0497 (5)0.1060 (4)0.0258 (17)0.667 (7)
H5BA0.1530611.0406390.0721910.031*0.667 (7)
C6B0.1304 (8)0.9961 (5)0.1564 (3)0.0209 (16)0.667 (7)
C7B0.0605 (7)0.9261 (4)0.1610 (3)0.0268 (14)0.667 (7)
H7BA0.0602540.8905820.1959450.032*0.667 (7)
C8B0.0037 (6)0.9091 (4)0.1185 (2)0.0276 (12)0.667 (7)
H8BA0.0029440.9429970.0827530.033*0.667 (7)
N1B0.1817 (5)0.8225 (2)0.10207 (19)0.0291 (10)0.667 (7)
C9B0.0749 (6)0.8374 (3)0.12805 (19)0.0269 (10)0.667 (7)
C10B0.0237 (4)0.77673 (17)0.17134 (15)0.0293 (10)0.667 (7)
H10B0.0675340.7768530.1748880.035*0.667 (7)
C11B0.0995 (4)0.7220 (2)0.20555 (17)0.0310 (10)0.667 (7)
H11B0.1904270.7230560.2018070.037*0.667 (7)
C12B0.0539 (6)0.6597 (2)0.24877 (17)0.0291 (10)0.667 (7)
C13B0.1395 (5)0.6162 (3)0.2913 (2)0.0331 (11)0.667 (7)
H13B0.2249290.6273230.2916090.040*0.667 (7)
C14B0.1013 (8)0.5567 (4)0.3331 (4)0.0309 (17)0.667 (7)
H14B0.1597260.5289000.3613640.037*0.667 (7)
C15B0.0261 (14)0.5392 (7)0.3321 (7)0.0276 (18)0.667 (7)
C16B0.1120 (6)0.5806 (4)0.2896 (3)0.0311 (15)0.667 (7)
H16B0.1959610.5680730.2883740.037*0.667 (7)
C17B0.0728 (6)0.6407 (3)0.2489 (2)0.0304 (10)0.667 (7)
H17B0.1322240.6689520.2212200.036*0.667 (7)
C1X0.139 (3)0.9949 (10)0.2158 (6)0.021 (3)0.333 (7)
H1XB0.1118340.9639160.2510900.025*0.333 (7)
C2X0.212 (4)1.0607 (11)0.2108 (9)0.029 (4)0.333 (7)
H2XB0.2338061.0723270.2431530.035*0.333 (7)
C3X0.253 (2)1.1094 (8)0.1593 (8)0.029 (4)0.333 (7)
C4X0.221 (2)1.0902 (8)0.1111 (6)0.026 (4)0.333 (7)
H4XB0.2479861.1215960.0759050.031*0.333 (7)
C5X0.1507 (19)1.0247 (8)0.1159 (7)0.026 (4)0.333 (7)
H5XB0.1318801.0125950.0834930.032*0.333 (7)
C6X0.1057 (17)0.9753 (8)0.1680 (7)0.023 (4)0.333 (7)
C7X0.0213 (13)0.9091 (8)0.1718 (6)0.030 (3)0.333 (7)
H7XB0.0108470.8759950.2077770.036*0.333 (7)
C8X0.0432 (11)0.8893 (6)0.1309 (4)0.022 (2)0.333 (7)
H8XB0.0290930.9187400.0938930.027*0.333 (7)
N1X0.2384 (10)0.8148 (5)0.1119 (4)0.0275 (19)0.333 (7)
C9X0.1350 (11)0.8235 (4)0.1415 (4)0.0262 (19)0.333 (7)
C10X0.1172 (8)0.7579 (5)0.1892 (3)0.030 (2)0.333 (7)
H10E0.1928810.7279150.2051730.036*0.333 (7)
C11X0.0016 (7)0.7388 (3)0.2107 (3)0.032 (2)0.333 (7)
H11E0.0738710.7707510.1974300.039*0.333 (7)
C12X0.0153 (12)0.6696 (4)0.2549 (3)0.0274 (18)0.333 (7)
C13X0.0832 (11)0.6316 (5)0.2930 (4)0.031 (2)0.333 (7)
H13E0.1622990.6497560.2930770.038*0.333 (7)
C14X0.0608 (17)0.5656 (9)0.3311 (9)0.040 (5)0.333 (7)
H14E0.1264580.5400560.3567820.048*0.333 (7)
C15X0.055 (3)0.5364 (16)0.3323 (16)0.039 (6)0.333 (7)
C16X0.1558 (12)0.5768 (7)0.2966 (7)0.028 (3)0.333 (7)
H16E0.2375040.5604580.2985400.033*0.333 (7)
C17X0.1335 (12)0.6423 (5)0.2579 (4)0.034 (2)0.333 (7)
H17E0.2005910.6685450.2331160.040*0.333 (7)
S1D0.8699 (3)0.79428 (15)0.04235 (14)0.0365 (7)0.653 (15)
C19D0.9873 (8)0.7925 (4)0.0153 (4)0.051 (2)0.653 (15)
H19I0.9507820.8253420.0505510.061*0.653 (15)
H19J1.0693600.8080080.0089950.061*0.653 (15)
C20D1.0154 (10)0.7177 (4)0.0193 (5)0.044 (4)0.653 (15)
C21D1.1364 (9)0.6760 (6)0.0038 (8)0.061 (4)0.653 (15)
H21E1.2003160.6928830.0115660.073*0.653 (15)
C22D1.1633 (10)0.6110 (5)0.0105 (6)0.085 (4)0.653 (15)
H22E1.2462920.5846900.0015060.102*0.653 (15)
C23D1.0684 (8)0.5845 (4)0.0306 (5)0.074 (3)0.653 (15)
H23E1.0875460.5399820.0351080.088*0.653 (15)
C24D0.9478 (9)0.6212 (6)0.0441 (5)0.071 (3)0.653 (15)
H24E0.8835430.6022400.0574840.085*0.653 (15)
C25D0.9208 (10)0.6879 (6)0.0376 (7)0.054 (3)0.653 (15)
H25E0.8367060.7130900.0457800.065*0.653 (15)
S1Y0.8920 (8)0.7789 (5)0.0574 (5)0.0813 (19)0.347 (15)
C19Y1.0241 (12)0.7814 (8)0.0076 (8)0.054 (4)0.347 (15)
H19G1.0139280.8268360.0226230.065*0.347 (15)
H19H1.1080930.7762860.0256580.065*0.347 (15)
C20Y1.0216 (16)0.7214 (10)0.0157 (9)0.044 (8)0.347 (15)
C21Y1.1406 (16)0.6813 (10)0.0196 (13)0.056 (6)0.347 (15)
H21D1.2179870.6936530.0095280.067*0.347 (15)
C22Y1.1474 (18)0.6241 (9)0.0378 (9)0.077 (6)0.347 (15)
H22D1.2268800.5947440.0366200.092*0.347 (15)
C23Y1.036 (2)0.6105 (11)0.0579 (9)0.090 (7)0.347 (15)
H23D1.0389450.5719690.0708400.109*0.347 (15)
C24Y0.9215 (19)0.6529 (12)0.0588 (9)0.068 (5)0.347 (15)
H24D0.8456720.6424750.0717390.082*0.347 (15)
C25Y0.913 (2)0.7121 (10)0.0411 (12)0.051 (4)0.347 (15)
H25D0.8364400.7443720.0463560.061*0.347 (15)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0301 (3)0.0200 (2)0.0393 (3)0.00488 (19)0.0081 (2)0.0098 (2)
S2A0.0309 (3)0.0217 (2)0.0313 (3)0.00635 (19)0.0073 (2)0.0069 (2)
N1A0.0334 (9)0.0227 (8)0.0307 (10)0.0076 (7)0.0069 (8)0.0084 (7)
N2A0.0315 (9)0.0186 (9)0.0308 (10)0.0053 (7)0.0080 (8)0.0071 (7)
O1A0.0435 (10)0.0347 (9)0.0599 (12)0.0027 (7)0.0104 (9)0.0222 (8)
O2A0.0482 (10)0.0340 (9)0.0518 (12)0.0091 (8)0.0051 (9)0.0102 (8)
C1A0.0329 (11)0.0358 (12)0.0340 (12)0.0105 (9)0.0066 (9)0.0164 (10)
C2A0.0289 (11)0.0418 (13)0.0427 (14)0.0057 (9)0.0079 (10)0.0220 (11)
C3A0.0355 (12)0.0335 (12)0.0360 (13)0.0008 (9)0.0002 (10)0.0160 (10)
C4A0.0425 (13)0.0291 (11)0.0336 (13)0.0061 (9)0.0085 (10)0.0096 (10)
C5A0.0345 (11)0.0310 (11)0.0292 (12)0.0043 (9)0.0079 (9)0.0114 (9)
C6A0.0308 (11)0.0302 (11)0.0236 (11)0.0048 (8)0.0012 (9)0.0115 (9)
C7A0.0345 (11)0.0278 (11)0.0247 (11)0.0080 (9)0.0037 (9)0.0105 (9)
C8A0.0357 (11)0.0243 (10)0.0255 (11)0.0065 (8)0.0054 (9)0.0066 (9)
C9A0.0334 (11)0.0264 (10)0.0248 (11)0.0044 (8)0.0031 (9)0.0091 (9)
C10A0.0355 (11)0.0252 (10)0.0288 (11)0.0063 (9)0.0078 (9)0.0088 (9)
C11A0.0356 (12)0.0279 (11)0.0344 (12)0.0074 (9)0.0069 (10)0.0100 (9)
C12A0.0370 (12)0.0236 (10)0.0344 (12)0.0033 (9)0.0035 (10)0.0089 (9)
C13A0.0355 (12)0.0296 (11)0.0458 (15)0.0045 (9)0.0003 (11)0.0102 (10)
C14A0.0423 (13)0.0287 (12)0.0438 (15)0.0006 (10)0.0083 (11)0.0043 (10)
C15A0.0448 (13)0.0235 (11)0.0390 (14)0.0051 (9)0.0014 (11)0.0015 (10)
C16A0.0364 (12)0.0304 (12)0.0414 (14)0.0062 (9)0.0001 (10)0.0056 (10)
C17A0.0369 (12)0.0258 (11)0.0335 (12)0.0035 (9)0.0018 (10)0.0036 (9)
C18A0.0306 (11)0.0233 (10)0.0258 (11)0.0038 (8)0.0009 (9)0.0090 (8)
C19A0.0344 (12)0.0324 (12)0.0737 (19)0.0117 (10)0.0225 (12)0.0260 (13)
C20A0.0254 (10)0.0238 (10)0.0436 (13)0.0058 (8)0.0105 (9)0.0119 (9)
C21A0.0333 (12)0.0342 (12)0.0445 (15)0.0024 (9)0.0027 (11)0.0050 (11)
C22A0.0421 (13)0.0490 (15)0.0387 (14)0.0095 (11)0.0008 (11)0.0183 (12)
C23A0.0412 (13)0.0300 (12)0.0452 (14)0.0088 (10)0.0116 (11)0.0193 (11)
C24A0.0448 (13)0.0256 (11)0.0402 (14)0.0024 (10)0.0022 (11)0.0064 (10)
C25A0.0358 (12)0.0361 (12)0.0320 (12)0.0030 (9)0.0021 (10)0.0138 (10)
C26A0.0396 (15)0.0581 (18)0.103 (3)0.0019 (13)0.0169 (16)0.0499 (19)
C27A0.0535 (17)0.0412 (15)0.0609 (19)0.0163 (12)0.0006 (14)0.0159 (13)
S1B0.0543 (3)0.0217 (3)0.0302 (3)0.0108 (2)0.0017 (3)0.0054 (2)
S2B0.0332 (3)0.0219 (2)0.0328 (3)0.0084 (2)0.0018 (2)0.0040 (2)
N2B0.0628 (14)0.0239 (10)0.0314 (11)0.0189 (9)0.0156 (10)0.0112 (8)
O1B0.0473 (11)0.0752 (14)0.0357 (10)0.0109 (10)0.0045 (8)0.0181 (9)
O2B0.0474 (10)0.0287 (8)0.0323 (9)0.0060 (7)0.0001 (7)0.0015 (7)
C18B0.0459 (13)0.0242 (10)0.0245 (11)0.0113 (9)0.0045 (10)0.0072 (9)
C19B0.0366 (13)0.0252 (12)0.0653 (18)0.0047 (9)0.0082 (12)0.0087 (11)
C20B0.0368 (12)0.0258 (11)0.0392 (13)0.0058 (9)0.0057 (10)0.0032 (10)
C21B0.0485 (15)0.0496 (15)0.0412 (15)0.0040 (12)0.0010 (12)0.0063 (12)
C22B0.0634 (19)0.073 (2)0.0441 (17)0.0195 (16)0.0089 (14)0.0273 (15)
C23B0.075 (2)0.0416 (15)0.0479 (17)0.0237 (14)0.0275 (15)0.0219 (13)
C24B0.0726 (19)0.0271 (12)0.0473 (16)0.0031 (12)0.0079 (14)0.0067 (11)
C25B0.0520 (15)0.0334 (13)0.0436 (15)0.0029 (11)0.0059 (12)0.0111 (11)
C26B0.0617 (18)0.070 (2)0.0434 (17)0.0083 (15)0.0038 (14)0.0234 (15)
C27B0.0524 (15)0.0433 (14)0.0417 (15)0.0127 (12)0.0022 (12)0.0095 (12)
S1C0.0381 (3)0.0262 (3)0.0332 (3)0.0085 (2)0.0095 (2)0.0076 (2)
S2C0.0535 (4)0.0247 (3)0.0479 (4)0.0063 (2)0.0203 (3)0.0055 (3)
N1C0.0368 (10)0.0285 (9)0.0274 (10)0.0124 (8)0.0036 (8)0.0062 (8)
N2C0.0369 (10)0.0225 (9)0.0307 (10)0.0068 (7)0.0037 (8)0.0051 (8)
O1C0.0427 (9)0.0333 (9)0.0479 (11)0.0034 (7)0.0099 (8)0.0113 (8)
O2C0.0723 (14)0.0424 (11)0.0485 (12)0.0232 (10)0.0037 (10)0.0108 (9)
C1C0.0398 (13)0.0328 (12)0.0324 (13)0.0032 (10)0.0070 (10)0.0007 (10)
C2C0.0378 (12)0.0419 (13)0.0269 (12)0.0038 (10)0.0039 (10)0.0047 (10)
C3C0.0304 (11)0.0306 (11)0.0341 (12)0.0024 (9)0.0026 (9)0.0081 (9)
C4C0.0413 (13)0.0323 (12)0.0354 (13)0.0034 (10)0.0087 (11)0.0022 (10)
C5C0.0380 (12)0.0365 (12)0.0293 (12)0.0009 (10)0.0068 (10)0.0014 (10)
C6C0.0299 (11)0.0331 (11)0.0290 (12)0.0068 (9)0.0004 (9)0.0056 (9)
C7C0.0364 (12)0.0270 (11)0.0339 (12)0.0079 (9)0.0025 (10)0.0032 (9)
C8C0.0389 (12)0.0277 (11)0.0235 (11)0.0112 (9)0.0031 (9)0.0039 (9)
C9C0.0327 (11)0.0291 (11)0.0280 (11)0.0077 (9)0.0017 (9)0.0092 (9)
C10C0.0339 (11)0.0321 (12)0.0265 (11)0.0062 (9)0.0078 (9)0.0063 (9)
C11C0.0356 (12)0.0317 (12)0.0271 (12)0.0077 (9)0.0042 (9)0.0071 (9)
C12C0.0311 (11)0.0310 (11)0.0316 (12)0.0081 (9)0.0002 (9)0.0052 (9)
C13C0.0532 (15)0.0320 (12)0.0350 (13)0.0111 (11)0.0006 (11)0.0093 (10)
C14C0.0563 (16)0.0306 (12)0.0463 (16)0.0123 (11)0.0056 (12)0.0066 (11)
C15C0.0431 (14)0.0374 (13)0.0394 (14)0.0152 (11)0.0012 (11)0.0034 (11)
C16C0.0387 (13)0.0445 (14)0.0328 (13)0.0083 (10)0.0061 (10)0.0030 (11)
C17C0.0333 (11)0.0330 (12)0.0331 (13)0.0055 (9)0.0036 (10)0.0065 (10)
C18C0.0307 (11)0.0403 (13)0.0373 (13)0.0051 (9)0.0026 (10)0.0196 (10)
C19C0.0370 (12)0.0304 (11)0.0377 (13)0.0084 (9)0.0116 (10)0.0090 (10)
C20C0.0329 (11)0.0272 (11)0.0285 (11)0.0073 (9)0.0076 (9)0.0057 (9)
C21C0.0338 (12)0.0352 (13)0.0499 (15)0.0066 (10)0.0005 (11)0.0106 (11)
C22C0.0405 (14)0.0351 (14)0.072 (2)0.0016 (11)0.0072 (13)0.0111 (13)
C23C0.0533 (16)0.0315 (13)0.0578 (17)0.0107 (11)0.0216 (13)0.0182 (12)
C24C0.0499 (15)0.0432 (14)0.0460 (15)0.0161 (11)0.0081 (12)0.0226 (12)
C25C0.0337 (12)0.0391 (13)0.0386 (14)0.0047 (10)0.0020 (10)0.0106 (11)
C26C0.0379 (13)0.0456 (14)0.0449 (15)0.0023 (11)0.0025 (11)0.0192 (12)
C27C0.105 (3)0.0408 (17)0.071 (2)0.0374 (18)0.011 (2)0.0111 (15)
S2D0.0492 (4)0.0477 (4)0.0563 (4)0.0066 (3)0.0186 (3)0.0207 (3)
N1D0.0320 (10)0.0413 (11)0.0354 (11)0.0110 (8)0.0014 (8)0.0079 (9)
N2D0.0332 (10)0.0341 (11)0.0376 (11)0.0052 (8)0.0027 (8)0.0106 (9)
O1D0.0450 (10)0.0380 (9)0.0616 (12)0.0128 (8)0.0166 (9)0.0233 (9)
O2D0.0618 (12)0.0322 (9)0.0441 (11)0.0108 (8)0.0040 (9)0.0033 (8)
C1D0.0349 (12)0.0310 (12)0.0423 (14)0.0131 (9)0.0062 (10)0.0098 (10)
C2D0.0347 (12)0.0392 (13)0.0432 (14)0.0128 (10)0.0095 (11)0.0124 (11)
C3D0.0416 (13)0.0306 (11)0.0343 (13)0.0102 (10)0.0081 (10)0.0109 (10)
C4D0.0401 (13)0.0372 (13)0.0425 (14)0.0190 (10)0.0108 (11)0.0129 (11)
C5D0.0349 (12)0.0365 (12)0.0361 (13)0.0130 (10)0.0101 (10)0.0098 (10)
C6D0.0341 (11)0.0335 (11)0.0232 (11)0.0119 (9)0.0021 (9)0.0045 (9)
C7D0.0321 (11)0.0299 (11)0.0253 (11)0.0101 (9)0.0016 (9)0.0044 (9)
C8D0.0339 (11)0.0347 (12)0.0224 (11)0.0112 (9)0.0008 (9)0.0039 (9)
C9D0.0268 (11)0.0372 (12)0.0291 (12)0.0045 (9)0.0015 (9)0.0107 (10)
C10D0.0300 (11)0.0374 (12)0.0298 (12)0.0061 (9)0.0007 (9)0.0069 (10)
C11D0.0400 (13)0.0374 (12)0.0301 (12)0.0033 (10)0.0059 (10)0.0109 (10)
C12D0.0401 (13)0.0345 (12)0.0321 (13)0.0044 (10)0.0061 (10)0.0071 (10)
C13D0.0727 (19)0.0376 (13)0.0355 (14)0.0083 (12)0.0067 (13)0.0132 (11)
C14D0.0716 (19)0.0338 (13)0.0421 (15)0.0105 (12)0.0076 (13)0.0111 (11)
C15D0.0424 (13)0.0351 (13)0.0419 (14)0.0062 (10)0.0050 (11)0.0072 (11)
C16D0.0382 (13)0.0396 (13)0.0360 (13)0.0058 (10)0.0048 (10)0.0101 (11)
C17D0.0334 (12)0.0319 (12)0.0401 (13)0.0034 (9)0.0005 (10)0.0111 (10)
C18D0.0307 (12)0.0566 (16)0.0632 (18)0.0055 (11)0.0055 (12)0.0428 (14)
C26D0.0476 (15)0.0446 (15)0.073 (2)0.0082 (12)0.0203 (14)0.0268 (14)
C27D0.073 (2)0.0348 (14)0.0557 (18)0.0164 (13)0.0096 (15)0.0062 (12)
C1B0.034 (4)0.028 (5)0.017 (3)0.006 (3)0.003 (3)0.003 (3)
C2B0.031 (3)0.036 (6)0.028 (4)0.006 (5)0.003 (3)0.017 (4)
C3B0.031 (3)0.038 (5)0.026 (3)0.013 (4)0.0024 (18)0.013 (3)
C4B0.029 (2)0.029 (4)0.028 (3)0.005 (4)0.0014 (18)0.007 (3)
C5B0.025 (3)0.032 (5)0.018 (3)0.004 (4)0.001 (2)0.005 (3)
C6B0.023 (3)0.023 (4)0.014 (4)0.005 (2)0.002 (3)0.001 (3)
C7B0.026 (3)0.028 (4)0.027 (3)0.010 (2)0.006 (2)0.008 (2)
C8B0.032 (3)0.024 (3)0.026 (3)0.007 (2)0.0022 (19)0.006 (2)
N1B0.034 (2)0.0267 (18)0.028 (2)0.0109 (19)0.0058 (19)0.0091 (15)
C9B0.028 (2)0.028 (2)0.029 (2)0.009 (2)0.0063 (18)0.0129 (17)
C10B0.034 (2)0.0270 (18)0.029 (2)0.0110 (15)0.0112 (16)0.0103 (16)
C11B0.032 (2)0.026 (2)0.037 (2)0.0098 (19)0.0076 (16)0.0130 (19)
C12B0.031 (3)0.0264 (19)0.031 (2)0.0069 (18)0.0028 (19)0.0100 (17)
C13B0.029 (3)0.032 (2)0.040 (2)0.004 (2)0.000 (2)0.0135 (18)
C14B0.032 (4)0.026 (3)0.034 (3)0.004 (3)0.009 (3)0.007 (2)
C15B0.036 (5)0.020 (3)0.026 (3)0.007 (3)0.005 (3)0.005 (2)
C16B0.025 (3)0.035 (3)0.035 (3)0.011 (2)0.003 (3)0.012 (2)
C17B0.031 (3)0.027 (2)0.030 (2)0.005 (2)0.003 (2)0.0031 (16)
C1X0.028 (7)0.021 (8)0.009 (5)0.000 (5)0.003 (4)0.000 (5)
C2X0.047 (8)0.016 (9)0.022 (6)0.011 (7)0.003 (4)0.001 (4)
C3X0.019 (4)0.019 (7)0.053 (8)0.005 (5)0.004 (4)0.017 (5)
C4X0.031 (6)0.027 (10)0.021 (5)0.011 (9)0.001 (4)0.005 (6)
C5X0.027 (6)0.019 (8)0.028 (9)0.001 (6)0.004 (5)0.003 (7)
C6X0.027 (7)0.018 (8)0.014 (6)0.006 (5)0.010 (4)0.011 (5)
C7X0.030 (7)0.025 (6)0.044 (7)0.007 (4)0.001 (5)0.020 (5)
C8X0.025 (6)0.022 (7)0.016 (5)0.010 (4)0.004 (4)0.001 (4)
N1X0.032 (5)0.023 (3)0.030 (4)0.009 (4)0.008 (4)0.012 (3)
C9X0.027 (5)0.025 (4)0.033 (5)0.010 (4)0.006 (4)0.017 (3)
C10X0.032 (5)0.027 (5)0.035 (5)0.002 (3)0.000 (3)0.014 (4)
C11X0.035 (5)0.027 (4)0.035 (5)0.003 (3)0.001 (3)0.013 (3)
C12X0.031 (5)0.026 (4)0.026 (4)0.008 (4)0.010 (4)0.010 (3)
C13X0.034 (6)0.025 (5)0.037 (5)0.011 (4)0.007 (5)0.011 (4)
C14X0.043 (11)0.041 (7)0.028 (5)0.010 (7)0.018 (7)0.006 (4)
C15X0.047 (12)0.034 (8)0.044 (9)0.015 (7)0.007 (8)0.020 (7)
C16X0.028 (6)0.015 (4)0.034 (5)0.006 (4)0.008 (5)0.000 (3)
C17X0.034 (6)0.028 (4)0.036 (5)0.000 (4)0.002 (4)0.008 (3)
S1D0.0330 (8)0.0158 (8)0.0538 (12)0.0001 (6)0.0177 (7)0.0066 (7)
C19D0.046 (4)0.040 (3)0.061 (4)0.007 (3)0.028 (3)0.012 (3)
C20D0.041 (7)0.025 (4)0.055 (6)0.000 (4)0.004 (4)0.001 (4)
C21D0.043 (4)0.054 (5)0.088 (10)0.013 (4)0.018 (4)0.034 (6)
C22D0.057 (4)0.044 (4)0.149 (11)0.006 (3)0.009 (5)0.029 (5)
C23D0.070 (4)0.052 (4)0.110 (7)0.029 (3)0.043 (5)0.039 (4)
C24D0.071 (6)0.087 (7)0.069 (6)0.054 (5)0.016 (4)0.030 (5)
C25D0.036 (3)0.046 (6)0.066 (5)0.007 (4)0.001 (3)0.001 (6)
S1Y0.040 (2)0.055 (3)0.114 (4)0.0129 (18)0.018 (2)0.020 (3)
C19Y0.028 (5)0.041 (6)0.098 (12)0.013 (4)0.019 (6)0.030 (8)
C20Y0.029 (11)0.061 (13)0.053 (11)0.025 (8)0.028 (8)0.032 (9)
C21Y0.050 (8)0.041 (7)0.075 (14)0.031 (7)0.004 (6)0.006 (6)
C22Y0.070 (9)0.039 (7)0.120 (16)0.013 (6)0.013 (9)0.030 (9)
C23Y0.133 (19)0.078 (12)0.088 (13)0.067 (13)0.035 (12)0.048 (10)
C24Y0.082 (10)0.080 (13)0.059 (10)0.054 (10)0.020 (7)0.028 (10)
C25Y0.043 (7)0.041 (10)0.055 (7)0.007 (6)0.007 (5)0.003 (9)
Geometric parameters (Å, º) top
S1A—C18A1.760 (2)C24C—H24C0.9300
S1A—C19A1.814 (2)C25C—H25C0.9300
S2A—C18A1.661 (2)C26C—H26G0.9600
N1A—C9A1.298 (3)C26C—H26H0.9600
N1A—N2A1.371 (3)C26C—H26I0.9600
N2A—C18A1.344 (3)C27C—H27G0.9600
N2A—H1N20.81 (3)C27C—H27H0.9600
O1A—C3A1.367 (3)C27C—H27I0.9600
O1A—C26A1.414 (3)S2D—C18D1.621 (3)
O2A—C15A1.369 (3)N1D—C9D1.317 (3)
O2A—C27A1.435 (3)N1D—N2D1.354 (3)
C1A—C6A1.384 (3)N2D—C18D1.367 (3)
C1A—C2A1.391 (3)N2D—H4N20.91 (4)
C1A—H1AA0.9300O1D—C3D1.367 (3)
C2A—C3A1.386 (3)O1D—C26D1.428 (3)
C2A—H2AA0.9300O2D—C15D1.366 (3)
C3A—C4A1.389 (3)O2D—C27D1.434 (3)
C4A—C5A1.375 (3)C1D—C2D1.382 (3)
C4A—H4AA0.9300C1D—C6D1.393 (3)
C5A—C6A1.405 (3)C1D—H1DA0.9300
C5A—H5AA0.9300C2D—C3D1.391 (3)
C6A—C7A1.464 (3)C2D—H2DA0.9300
C7A—C8A1.332 (3)C3D—C4D1.391 (3)
C7A—H7AA0.9300C4D—C5D1.373 (3)
C8A—C9A1.462 (3)C4D—H4DA0.9300
C8A—H8AA0.9300C5D—C6D1.402 (3)
C9A—C10A1.476 (3)C5D—H5DA0.9300
C10A—C11A1.337 (3)C6D—C7D1.458 (3)
C10A—H10A0.9300C7D—C8D1.340 (3)
C11A—C12A1.467 (3)C7D—H7DA0.9300
C11A—H11A0.9300C8D—C9D1.463 (3)
C12A—C17A1.397 (3)C8D—H8DA0.9300
C12A—C13A1.398 (3)C9D—C10D1.471 (3)
C13A—C14A1.380 (3)C10D—C11D1.337 (3)
C13A—H13A0.9300C10D—H10D0.9300
C14A—C15A1.392 (4)C11D—C12D1.461 (3)
C14A—H14A0.9300C11D—H11D0.9300
C15A—C16A1.390 (3)C12D—C13D1.395 (3)
C16A—C17A1.390 (3)C12D—C17D1.403 (4)
C16A—H16A0.9300C13D—C14D1.380 (4)
C17A—H17A0.9300C13D—H13D0.9300
C19A—C20A1.508 (3)C14D—C15D1.385 (4)
C19A—H19A0.9700C14D—H14D0.9300
C19A—H19B0.9700C15D—C16D1.396 (4)
C20A—C21A1.383 (4)C16D—C17D1.378 (3)
C20A—C25A1.391 (3)C16D—H16D0.9300
C21A—C22A1.381 (4)C17D—H17D0.9300
C21A—H21A0.9300C18D—S1D1.709 (4)
C22A—C23A1.378 (4)C18D—S1Y2.032 (11)
C22A—H22A0.9300C26D—H26J0.9600
C23A—C24A1.372 (4)C26D—H26K0.9600
C23A—H23A0.9300C26D—H26L0.9600
C24A—C25A1.389 (3)C27D—H27J0.9600
C24A—H24A0.9300C27D—H27K0.9600
C25A—H25A0.9300C27D—H27L0.9600
C26A—H26A0.9600C1B—C2B1.382 (9)
C26A—H26B0.9600C1B—C6B1.396 (7)
C26A—H26C0.9600C1B—H1BA0.9300
C27A—H27A0.9600C2B—C3B1.384 (8)
C27A—H27B0.9600C2B—H2BA0.9300
C27A—H27C0.9600C3B—C4B1.397 (8)
S1B—C18B1.755 (2)C4B—C5B1.381 (7)
S1B—C19B1.804 (3)C4B—H4BA0.9300
S2B—C18B1.657 (2)C5B—C6B1.396 (7)
N2B—C18B1.348 (3)C5B—H5BA0.9300
N2B—N1X1.393 (9)C6B—C7B1.454 (7)
N2B—N1B1.402 (5)C7B—C8B1.342 (7)
N2B—H2N20.82 (3)C7B—H7BA0.9300
O1B—C3B1.248 (9)C8B—C9B1.466 (6)
O1B—C26B1.423 (3)C8B—H8BA0.9300
O1B—C3X1.613 (16)N1B—C9B1.292 (6)
O2B—C15X1.309 (19)C9B—C10B1.473 (5)
O2B—C15B1.406 (9)C10B—C11B1.325 (6)
O2B—C27B1.426 (3)C10B—H10B0.9300
C19B—C20B1.509 (3)C11B—C12B1.468 (6)
C19B—H19C0.9700C11B—H11B0.9300
C19B—H19D0.9700C12B—C13B1.394 (7)
C20B—C21B1.375 (4)C12B—C17B1.396 (6)
C20B—C25B1.384 (3)C13B—C14B1.390 (7)
C21B—C22B1.381 (4)C13B—H13B0.9300
C21B—H21B0.9300C14B—C15B1.395 (9)
C22B—C23B1.369 (5)C14B—H14B0.9300
C22B—H22B0.9300C15B—C16B1.384 (8)
C23B—C24B1.372 (4)C16B—C17B1.389 (7)
C23B—H23B0.9300C16B—H16B0.9300
C24B—C25B1.388 (4)C17B—H17B0.9300
C24B—H24B0.9300C1X—C2X1.390 (14)
C25B—H25B0.9300C1X—C6X1.400 (13)
C26B—H26D0.9600C1X—H1XB0.9300
C26B—H26E0.9600C2X—C3X1.385 (14)
C26B—H26F0.9600C2X—H2XB0.9300
C27B—H27D0.9600C3X—C4X1.403 (14)
C27B—H27E0.9600C4X—C5X1.377 (12)
C27B—H27F0.9600C4X—H4XB0.9300
S1C—C18C1.763 (2)C5X—C6X1.412 (12)
S1C—C19C1.825 (2)C5X—H5XB0.9300
S2C—C18C1.648 (3)C6X—C7X1.456 (12)
N1C—C9C1.314 (3)C7X—C8X1.336 (12)
N1C—N2C1.362 (3)C7X—H7XB0.9300
N2C—C18C1.352 (3)C8X—C9X1.463 (11)
N2C—H3N20.91 (3)C8X—H8XB0.9300
O1C—C3C1.370 (3)N1X—C9X1.284 (11)
O1C—C26C1.427 (3)C9X—C10X1.482 (11)
O2C—C15C1.366 (3)C10X—C11X1.321 (10)
O2C—C27C1.436 (4)C10X—H10E0.9300
C1C—C2C1.380 (3)C11X—C12X1.486 (9)
C1C—C6C1.389 (3)C11X—H11E0.9300
C1C—H1CA0.9300C12X—C17X1.379 (11)
C2C—C3C1.382 (3)C12X—C13X1.387 (12)
C2C—H2CA0.9300C13X—C14X1.390 (13)
C3C—C4C1.386 (3)C13X—H13E0.9300
C4C—C5C1.375 (3)C14X—C15X1.387 (15)
C4C—H4CA0.9300C14X—H14E0.9300
C5C—C6C1.400 (3)C15X—C16X1.378 (14)
C5C—H5CA0.9300C16X—C17X1.388 (13)
C6C—C7C1.466 (3)C16X—H16E0.9300
C7C—C8C1.331 (3)C17X—H17E0.9300
C7C—H7CA0.9300S1D—C19D1.841 (6)
C8C—C9C1.460 (3)C19D—C20D1.520 (8)
C8C—H8CA0.9300C19D—H19I0.9700
C9C—C10C1.476 (3)C19D—H19J0.9700
C10C—C11C1.324 (3)C20D—C25D1.375 (10)
C10C—H10C0.9300C20D—C21D1.388 (8)
C11C—C12C1.471 (3)C21D—C22D1.358 (9)
C11C—H11C0.9300C21D—H21E0.9300
C12C—C13C1.392 (3)C22D—C23D1.359 (11)
C12C—C17C1.398 (3)C22D—H22E0.9300
C13C—C14C1.393 (4)C23D—C24D1.342 (13)
C13C—H13C0.9300C23D—H23E0.9300
C14C—C15C1.373 (4)C24D—C25D1.390 (11)
C14C—H14C0.9300C24D—H24E0.9300
C15C—C16C1.394 (4)C25D—H25E0.9300
C16C—C17C1.376 (3)S1Y—C19Y1.785 (12)
C16C—H16C0.9300C19Y—C20Y1.508 (13)
C17C—H17C0.9300C19Y—H19G0.9700
C19C—C20C1.506 (3)C19Y—H19H0.9700
C19C—H19E0.9700C20Y—C25Y1.373 (14)
C19C—H19F0.9700C20Y—C21Y1.378 (13)
C20C—C25C1.390 (3)C21Y—C22Y1.362 (13)
C20C—C21C1.391 (3)C21Y—H21D0.9300
C21C—C22C1.384 (4)C22Y—C23Y1.367 (16)
C21C—H21C0.9300C22Y—H22D0.9300
C22C—C23C1.375 (4)C23Y—C24Y1.341 (18)
C22C—H22C0.9300C23Y—H23D0.9300
C23C—C24C1.369 (4)C24Y—C25Y1.389 (15)
C23C—H23C0.9300C24Y—H24D0.9300
C24C—C25C1.385 (3)C25Y—H25D0.9300
C18A—S1A—C19A101.27 (10)H26H—C26C—H26I109.5
C9A—N1A—N2A120.07 (17)O2C—C27C—H27G109.5
C18A—N2A—N1A118.15 (17)O2C—C27C—H27H109.5
C18A—N2A—H1N2115.8 (19)H27G—C27C—H27H109.5
N1A—N2A—H1N2126.1 (19)O2C—C27C—H27I109.5
C3A—O1A—C26A118.0 (2)H27G—C27C—H27I109.5
C15A—O2A—C27A117.6 (2)H27H—C27C—H27I109.5
C6A—C1A—C2A122.6 (2)C9D—N1D—N2D117.5 (2)
C6A—C1A—H1AA118.7N1D—N2D—C18D119.7 (2)
C2A—C1A—H1AA118.7N1D—N2D—H4N2125 (2)
C3A—C2A—C1A118.7 (2)C18D—N2D—H4N2115 (2)
C3A—C2A—H2AA120.6C3D—O1D—C26D117.54 (19)
C1A—C2A—H2AA120.6C15D—O2D—C27D117.7 (2)
O1A—C3A—C2A125.1 (2)C2D—C1D—C6D122.9 (2)
O1A—C3A—C4A115.0 (2)C2D—C1D—H1DA118.5
C2A—C3A—C4A119.8 (2)C6D—C1D—H1DA118.5
C5A—C4A—C3A120.7 (2)C1D—C2D—C3D118.7 (2)
C5A—C4A—H4AA119.7C1D—C2D—H2DA120.7
C3A—C4A—H4AA119.7C3D—C2D—H2DA120.7
C4A—C5A—C6A120.8 (2)O1D—C3D—C4D116.1 (2)
C4A—C5A—H5AA119.6O1D—C3D—C2D124.2 (2)
C6A—C5A—H5AA119.6C4D—C3D—C2D119.7 (2)
C1A—C6A—C5A117.3 (2)C5D—C4D—C3D120.6 (2)
C1A—C6A—C7A119.8 (2)C5D—C4D—H4DA119.7
C5A—C6A—C7A122.84 (19)C3D—C4D—H4DA119.7
C8A—C7A—C6A127.2 (2)C4D—C5D—C6D121.2 (2)
C8A—C7A—H7AA116.4C4D—C5D—H5DA119.4
C6A—C7A—H7AA116.4C6D—C5D—H5DA119.4
C7A—C8A—C9A125.1 (2)C1D—C6D—C5D116.8 (2)
C7A—C8A—H8AA117.5C1D—C6D—C7D119.51 (19)
C9A—C8A—H8AA117.5C5D—C6D—C7D123.6 (2)
N1A—C9A—C8A125.80 (19)C8D—C7D—C6D128.0 (2)
N1A—C9A—C10A114.22 (18)C8D—C7D—H7DA116.0
C8A—C9A—C10A119.91 (19)C6D—C7D—H7DA116.0
C11A—C10A—C9A122.3 (2)C7D—C8D—C9D123.8 (2)
C11A—C10A—H10A118.9C7D—C8D—H8DA118.1
C9A—C10A—H10A118.9C9D—C8D—H8DA118.1
C10A—C11A—C12A126.6 (2)N1D—C9D—C8D126.3 (2)
C10A—C11A—H11A116.7N1D—C9D—C10D114.7 (2)
C12A—C11A—H11A116.7C8D—C9D—C10D118.9 (2)
C17A—C12A—C13A117.3 (2)C11D—C10D—C9D125.1 (2)
C17A—C12A—C11A123.2 (2)C11D—C10D—H10D117.5
C13A—C12A—C11A119.5 (2)C9D—C10D—H10D117.5
C14A—C13A—C12A121.7 (2)C10D—C11D—C12D125.8 (2)
C14A—C13A—H13A119.2C10D—C11D—H11D117.1
C12A—C13A—H13A119.2C12D—C11D—H11D117.1
C13A—C14A—C15A119.9 (2)C13D—C12D—C17D116.7 (2)
C13A—C14A—H14A120.0C13D—C12D—C11D120.4 (2)
C15A—C14A—H14A120.0C17D—C12D—C11D122.9 (2)
O2A—C15A—C16A124.4 (2)C14D—C13D—C12D122.4 (3)
O2A—C15A—C14A115.8 (2)C14D—C13D—H13D118.8
C16A—C15A—C14A119.8 (2)C12D—C13D—H13D118.8
C17A—C16A—C15A119.5 (2)C13D—C14D—C15D119.8 (2)
C17A—C16A—H16A120.3C13D—C14D—H14D120.1
C15A—C16A—H16A120.3C15D—C14D—H14D120.1
C16A—C17A—C12A121.8 (2)O2D—C15D—C14D125.0 (2)
C16A—C17A—H17A119.1O2D—C15D—C16D115.7 (2)
C12A—C17A—H17A119.1C14D—C15D—C16D119.3 (2)
N2A—C18A—S2A121.55 (15)C17D—C16D—C15D120.1 (2)
N2A—C18A—S1A112.85 (15)C17D—C16D—H16D120.0
S2A—C18A—S1A125.60 (13)C15D—C16D—H16D120.0
C20A—C19A—S1A109.27 (15)C16D—C17D—C12D121.7 (2)
C20A—C19A—H19A109.8C16D—C17D—H17D119.1
S1A—C19A—H19A109.8C12D—C17D—H17D119.1
C20A—C19A—H19B109.8N2D—C18D—S2D122.8 (2)
S1A—C19A—H19B109.8N2D—C18D—S1D112.9 (2)
H19A—C19A—H19B108.3S2D—C18D—S1D124.23 (17)
C21A—C20A—C25A118.5 (2)N2D—C18D—S1Y109.0 (3)
C21A—C20A—C19A119.8 (2)S2D—C18D—S1Y128.0 (2)
C25A—C20A—C19A121.7 (2)O1D—C26D—H26J109.5
C22A—C21A—C20A121.2 (2)O1D—C26D—H26K109.5
C22A—C21A—H21A119.4H26J—C26D—H26K109.5
C20A—C21A—H21A119.4O1D—C26D—H26L109.5
C23A—C22A—C21A119.9 (2)H26J—C26D—H26L109.5
C23A—C22A—H22A120.1H26K—C26D—H26L109.5
C21A—C22A—H22A120.1O2D—C27D—H27J109.5
C24A—C23A—C22A119.8 (2)O2D—C27D—H27K109.5
C24A—C23A—H23A120.1H27J—C27D—H27K109.5
C22A—C23A—H23A120.1O2D—C27D—H27L109.5
C23A—C24A—C25A120.6 (2)H27J—C27D—H27L109.5
C23A—C24A—H24A119.7H27K—C27D—H27L109.5
C25A—C24A—H24A119.7C2B—C1B—C6B123.5 (7)
C24A—C25A—C20A120.0 (2)C2B—C1B—H1BA118.2
C24A—C25A—H25A120.0C6B—C1B—H1BA118.2
C20A—C25A—H25A120.0C1B—C2B—C3B118.2 (7)
O1A—C26A—H26A109.5C1B—C2B—H2BA120.9
O1A—C26A—H26B109.5C3B—C2B—H2BA120.9
H26A—C26A—H26B109.5O1B—C3B—C2B125.1 (7)
O1A—C26A—H26C109.5O1B—C3B—C4B114.9 (7)
H26A—C26A—H26C109.5C2B—C3B—C4B119.8 (7)
H26B—C26A—H26C109.5C5B—C4B—C3B120.8 (7)
O2A—C27A—H27A109.5C5B—C4B—H4BA119.6
O2A—C27A—H27B109.5C3B—C4B—H4BA119.6
H27A—C27A—H27B109.5C4B—C5B—C6B120.7 (7)
O2A—C27A—H27C109.5C4B—C5B—H5BA119.6
H27A—C27A—H27C109.5C6B—C5B—H5BA119.6
H27B—C27A—H27C109.5C5B—C6B—C1B116.8 (7)
C18B—S1B—C19B101.73 (11)C5B—C6B—C7B125.0 (6)
C18B—N2B—N1X107.4 (4)C1B—C6B—C7B118.1 (7)
C18B—N2B—N1B122.2 (3)C8B—C7B—C6B124.7 (6)
C18B—N2B—H2N2115.3 (19)C8B—C7B—H7BA117.7
N1X—N2B—H2N2133 (2)C6B—C7B—H7BA117.7
N1B—N2B—H2N2122.3 (19)C7B—C8B—C9B120.4 (5)
C3B—O1B—C26B117.6 (4)C7B—C8B—H8BA119.8
C26B—O1B—C3X116.9 (7)C9B—C8B—H8BA119.8
C15X—O2B—C27B108.6 (9)C9B—N1B—N2B121.8 (4)
C15B—O2B—C27B121.0 (4)N1B—C9B—C8B125.4 (4)
N2B—C18B—S2B122.09 (17)N1B—C9B—C10B116.2 (4)
N2B—C18B—S1B112.17 (16)C8B—C9B—C10B118.4 (4)
S2B—C18B—S1B125.72 (14)C11B—C10B—C9B124.1 (4)
C20B—C19B—S1B107.82 (16)C11B—C10B—H10B117.9
C20B—C19B—H19C110.1C9B—C10B—H10B117.9
S1B—C19B—H19C110.1C10B—C11B—C12B126.4 (4)
C20B—C19B—H19D110.1C10B—C11B—H11B116.8
S1B—C19B—H19D110.1C12B—C11B—H11B116.8
H19C—C19B—H19D108.5C13B—C12B—C17B117.4 (4)
C21B—C20B—C25B118.5 (2)C13B—C12B—C11B119.9 (4)
C21B—C20B—C19B120.1 (2)C17B—C12B—C11B122.7 (4)
C25B—C20B—C19B121.4 (2)C14B—C13B—C12B122.1 (5)
C20B—C21B—C22B121.0 (3)C14B—C13B—H13B118.9
C20B—C21B—H21B119.5C12B—C13B—H13B118.9
C22B—C21B—H21B119.5C13B—C14B—C15B119.0 (7)
C23B—C22B—C21B120.4 (3)C13B—C14B—H14B120.5
C23B—C22B—H22B119.8C15B—C14B—H14B120.5
C21B—C22B—H22B119.8C16B—C15B—C14B120.0 (7)
C22B—C23B—C24B119.2 (3)C16B—C15B—O2B123.7 (8)
C22B—C23B—H23B120.4C14B—C15B—O2B116.1 (6)
C24B—C23B—H23B120.4C15B—C16B—C17B120.1 (6)
C23B—C24B—C25B120.6 (3)C15B—C16B—H16B120.0
C23B—C24B—H24B119.7C17B—C16B—H16B120.0
C25B—C24B—H24B119.7C16B—C17B—C12B121.3 (4)
C20B—C25B—C24B120.2 (3)C16B—C17B—H17B119.3
C20B—C25B—H25B119.9C12B—C17B—H17B119.3
C24B—C25B—H25B119.9C2X—C1X—C6X120.2 (13)
O1B—C26B—H26D109.5C2X—C1X—H1XB119.9
O1B—C26B—H26E109.5C6X—C1X—H1XB119.9
H26D—C26B—H26E109.5C3X—C2X—C1X122.4 (15)
O1B—C26B—H26F109.5C3X—C2X—H2XB118.8
H26D—C26B—H26F109.5C1X—C2X—H2XB118.8
H26E—C26B—H26F109.5C2X—C3X—C4X118.0 (14)
O2B—C27B—H27D109.5C2X—C3X—O1B123.5 (13)
O2B—C27B—H27E109.5C4X—C3X—O1B117.8 (13)
H27D—C27B—H27E109.5C5X—C4X—C3X119.9 (13)
O2B—C27B—H27F109.5C5X—C4X—H4XB120.1
H27D—C27B—H27F109.5C3X—C4X—H4XB120.1
H27E—C27B—H27F109.5C4X—C5X—C6X122.6 (14)
C18C—S1C—C19C100.52 (11)C4X—C5X—H5XB118.7
C9C—N1C—N2C119.70 (18)C6X—C5X—H5XB118.7
C18C—N2C—N1C118.99 (19)C1X—C6X—C5X116.9 (12)
C18C—N2C—H3N2110 (2)C1X—C6X—C7X121.1 (13)
N1C—N2C—H3N2131 (2)C5X—C6X—C7X121.9 (13)
C3C—O1C—C26C117.62 (18)C8X—C7X—C6X129.0 (13)
C15C—O2C—C27C116.8 (3)C8X—C7X—H7XB115.5
C2C—C1C—C6C122.4 (2)C6X—C7X—H7XB115.5
C2C—C1C—H1CA118.8C7X—C8X—C9X123.2 (10)
C6C—C1C—H1CA118.8C7X—C8X—H8XB118.4
C1C—C2C—C3C119.4 (2)C9X—C8X—H8XB118.4
C1C—C2C—H2CA120.3C9X—N1X—N2B111.3 (7)
C3C—C2C—H2CA120.3N1X—C9X—C8X125.6 (8)
O1C—C3C—C2C124.0 (2)N1X—C9X—C10X112.0 (8)
O1C—C3C—C4C116.7 (2)C8X—C9X—C10X122.3 (8)
C2C—C3C—C4C119.2 (2)C11X—C10X—C9X124.8 (8)
C5C—C4C—C3C121.0 (2)C11X—C10X—H10E117.6
C5C—C4C—H4CA119.5C9X—C10X—H10E117.6
C3C—C4C—H4CA119.5C10X—C11X—C12X124.1 (8)
C4C—C5C—C6C120.7 (2)C10X—C11X—H11E118.0
C4C—C5C—H5CA119.7C12X—C11X—H11E118.0
C6C—C5C—H5CA119.7C17X—C12X—C13X119.0 (7)
C1C—C6C—C5C117.2 (2)C17X—C12X—C11X118.6 (8)
C1C—C6C—C7C118.6 (2)C13X—C12X—C11X122.5 (9)
C5C—C6C—C7C124.2 (2)C12X—C13X—C14X118.4 (10)
C8C—C7C—C6C127.7 (2)C12X—C13X—H13E120.8
C8C—C7C—H7CA116.2C14X—C13X—H13E120.8
C6C—C7C—H7CA116.2C15X—C14X—C13X122.7 (13)
C7C—C8C—C9C124.3 (2)C15X—C14X—H14E118.6
C7C—C8C—H8CA117.8C13X—C14X—H14E118.6
C9C—C8C—H8CA117.8O2B—C15X—C16X130.1 (16)
N1C—C9C—C8C126.8 (2)O2B—C15X—C14X111.3 (13)
N1C—C9C—C10C114.27 (19)C16X—C15X—C14X118.2 (15)
C8C—C9C—C10C118.89 (19)C15X—C16X—C17X119.3 (12)
C11C—C10C—C9C124.9 (2)C15X—C16X—H16E120.3
C11C—C10C—H10C117.5C17X—C16X—H16E120.3
C9C—C10C—H10C117.5C12X—C17X—C16X122.2 (9)
C10C—C11C—C12C125.9 (2)C12X—C17X—H17E118.9
C10C—C11C—H11C117.1C16X—C17X—H17E118.9
C12C—C11C—H11C117.1C18D—S1D—C19D101.7 (3)
C13C—C12C—C17C117.3 (2)C20D—C19D—S1D110.8 (6)
C13C—C12C—C11C119.6 (2)C20D—C19D—H19I109.5
C17C—C12C—C11C123.0 (2)S1D—C19D—H19I109.5
C12C—C13C—C14C121.8 (2)C20D—C19D—H19J109.5
C12C—C13C—H13C119.1S1D—C19D—H19J109.5
C14C—C13C—H13C119.1H19I—C19D—H19J108.1
C15C—C14C—C13C119.6 (2)C25D—C20D—C21D116.9 (7)
C15C—C14C—H14C120.2C25D—C20D—C19D121.2 (7)
C13C—C14C—H14C120.2C21D—C20D—C19D121.9 (8)
O2C—C15C—C14C125.2 (2)C22D—C21D—C20D121.4 (9)
O2C—C15C—C16C115.1 (2)C22D—C21D—H21E119.3
C14C—C15C—C16C119.7 (2)C20D—C21D—H21E119.3
C17C—C16C—C15C120.3 (2)C21D—C22D—C23D119.7 (8)
C17C—C16C—H16C119.8C21D—C22D—H22E120.2
C15C—C16C—H16C119.8C23D—C22D—H22E120.2
C16C—C17C—C12C121.2 (2)C24D—C23D—C22D121.6 (7)
C16C—C17C—H17C119.4C24D—C23D—H23E119.2
C12C—C17C—H17C119.4C22D—C23D—H23E119.2
N2C—C18C—S2C122.25 (18)C23D—C24D—C25D118.6 (8)
N2C—C18C—S1C113.37 (18)C23D—C24D—H24E120.7
S2C—C18C—S1C124.37 (14)C25D—C24D—H24E120.7
C20C—C19C—S1C108.63 (15)C20D—C25D—C24D121.6 (8)
C20C—C19C—H19E110.0C20D—C25D—H25E119.2
S1C—C19C—H19E110.0C24D—C25D—H25E119.2
C20C—C19C—H19F110.0C19Y—S1Y—C18D96.7 (5)
S1C—C19C—H19F110.0C20Y—C19Y—S1Y109.0 (9)
H19E—C19C—H19F108.3C20Y—C19Y—H19G109.9
C25C—C20C—C21C118.6 (2)S1Y—C19Y—H19G109.9
C25C—C20C—C19C120.9 (2)C20Y—C19Y—H19H109.9
C21C—C20C—C19C120.5 (2)S1Y—C19Y—H19H109.9
C22C—C21C—C20C120.5 (2)H19G—C19Y—H19H108.3
C22C—C21C—H21C119.8C25Y—C20Y—C21Y118.4 (14)
C20C—C21C—H21C119.8C25Y—C20Y—C19Y123.5 (14)
C23C—C22C—C21C120.3 (2)C21Y—C20Y—C19Y117.3 (13)
C23C—C22C—H22C119.9C22Y—C21Y—C20Y121.4 (13)
C21C—C22C—H22C119.9C22Y—C21Y—H21D119.3
C24C—C23C—C22C119.8 (2)C20Y—C21Y—H21D119.3
C24C—C23C—H23C120.1C21Y—C22Y—C23Y119.0 (14)
C22C—C23C—H23C120.1C21Y—C22Y—H22D120.5
C23C—C24C—C25C120.6 (2)C23Y—C22Y—H22D120.5
C23C—C24C—H24C119.7C24Y—C23Y—C22Y119.9 (13)
C25C—C24C—H24C119.7C24Y—C23Y—H23D120.1
C24C—C25C—C20C120.2 (2)C22Y—C23Y—H23D120.1
C24C—C25C—H25C119.9C23Y—C24Y—C25Y121.8 (15)
C20C—C25C—H25C119.9C23Y—C24Y—H24D119.1
O1C—C26C—H26G109.5C25Y—C24Y—H24D119.1
O1C—C26C—H26H109.5C20Y—C25Y—C24Y118.0 (15)
H26G—C26C—H26H109.5C20Y—C25Y—H25D121.0
O1C—C26C—H26I109.5C24Y—C25Y—H25D121.0
H26G—C26C—H26I109.5
C9A—N1A—N2A—C18A178.1 (2)C2D—C1D—C6D—C5D0.4 (4)
C6A—C1A—C2A—C3A0.1 (4)C2D—C1D—C6D—C7D178.3 (2)
C26A—O1A—C3A—C2A2.8 (4)C4D—C5D—C6D—C1D1.3 (4)
C26A—O1A—C3A—C4A178.7 (3)C4D—C5D—C6D—C7D177.3 (2)
C1A—C2A—C3A—O1A178.2 (2)C1D—C6D—C7D—C8D172.1 (2)
C1A—C2A—C3A—C4A0.3 (4)C5D—C6D—C7D—C8D9.3 (4)
O1A—C3A—C4A—C5A178.0 (2)C6D—C7D—C8D—C9D176.0 (2)
C2A—C3A—C4A—C5A0.6 (4)N2D—N1D—C9D—C8D7.2 (3)
C3A—C4A—C5A—C6A0.5 (4)N2D—N1D—C9D—C10D177.91 (19)
C2A—C1A—C6A—C5A0.2 (3)C7D—C8D—C9D—N1D156.8 (2)
C2A—C1A—C6A—C7A178.5 (2)C7D—C8D—C9D—C10D28.4 (3)
C4A—C5A—C6A—C1A0.1 (3)N1D—C9D—C10D—C11D15.4 (3)
C4A—C5A—C6A—C7A178.8 (2)C8D—C9D—C10D—C11D169.3 (2)
C1A—C6A—C7A—C8A175.4 (2)C9D—C10D—C11D—C12D172.4 (2)
C5A—C6A—C7A—C8A5.9 (4)C10D—C11D—C12D—C13D167.0 (3)
C6A—C7A—C8A—C9A178.1 (2)C10D—C11D—C12D—C17D15.9 (4)
N2A—N1A—C9A—C8A1.5 (3)C17D—C12D—C13D—C14D2.3 (4)
N2A—N1A—C9A—C10A175.53 (19)C11D—C12D—C13D—C14D179.6 (3)
C7A—C8A—C9A—N1A175.0 (2)C12D—C13D—C14D—C15D0.4 (5)
C7A—C8A—C9A—C10A8.1 (3)C27D—O2D—C15D—C14D0.7 (4)
N1A—C9A—C10A—C11A37.5 (3)C27D—O2D—C15D—C16D177.9 (2)
C8A—C9A—C10A—C11A139.7 (2)C13D—C14D—C15D—O2D179.4 (3)
C9A—C10A—C11A—C12A176.9 (2)C13D—C14D—C15D—C16D2.1 (4)
C10A—C11A—C12A—C17A19.6 (4)O2D—C15D—C16D—C17D178.8 (2)
C10A—C11A—C12A—C13A158.7 (2)C14D—C15D—C16D—C17D2.5 (4)
C17A—C12A—C13A—C14A1.0 (4)C15D—C16D—C17D—C12D0.5 (4)
C11A—C12A—C13A—C14A177.3 (2)C13D—C12D—C17D—C16D1.9 (4)
C12A—C13A—C14A—C15A1.2 (4)C11D—C12D—C17D—C16D179.1 (2)
C27A—O2A—C15A—C16A0.9 (4)N1D—N2D—C18D—S2D178.81 (18)
C27A—O2A—C15A—C14A179.9 (3)N1D—N2D—C18D—S1D2.6 (3)
C13A—C14A—C15A—O2A178.6 (2)N1D—N2D—C18D—S1Y6.9 (4)
C13A—C14A—C15A—C16A0.7 (4)C6B—C1B—C2B—C3B3 (2)
O2A—C15A—C16A—C17A179.0 (2)C26B—O1B—C3B—C2B7.3 (15)
C14A—C15A—C16A—C17A0.2 (4)C26B—O1B—C3B—C4B177.9 (7)
C15A—C16A—C17A—C12A0.1 (4)C1B—C2B—C3B—O1B173.4 (13)
C13A—C12A—C17A—C16A0.5 (3)C1B—C2B—C3B—C4B1 (2)
C11A—C12A—C17A—C16A177.8 (2)O1B—C3B—C4B—C5B175.3 (10)
N1A—N2A—C18A—S2A175.75 (15)C2B—C3B—C4B—C5B0.2 (18)
N1A—N2A—C18A—S1A3.4 (3)C3B—C4B—C5B—C6B0.1 (16)
C19A—S1A—C18A—N2A179.45 (18)C4B—C5B—C6B—C1B1.7 (15)
C19A—S1A—C18A—S2A1.47 (19)C4B—C5B—C6B—C7B176.6 (9)
C18A—S1A—C19A—C20A160.53 (19)C2B—C1B—C6B—C5B3 (2)
S1A—C19A—C20A—C21A96.9 (2)C2B—C1B—C6B—C7B175.2 (13)
S1A—C19A—C20A—C25A85.0 (2)C5B—C6B—C7B—C8B16.4 (14)
C25A—C20A—C21A—C22A1.1 (4)C1B—C6B—C7B—C8B162.0 (9)
C19A—C20A—C21A—C22A177.1 (2)C6B—C7B—C8B—C9B178.0 (7)
C20A—C21A—C22A—C23A0.9 (4)C18B—N2B—N1B—C9B175.6 (4)
C21A—C22A—C23A—C24A0.1 (4)N2B—N1B—C9B—C8B8.6 (7)
C22A—C23A—C24A—C25A0.5 (4)N2B—N1B—C9B—C10B170.3 (4)
C23A—C24A—C25A—C20A0.3 (4)C7B—C8B—C9B—N1B147.3 (6)
C21A—C20A—C25A—C24A0.5 (3)C7B—C8B—C9B—C10B31.5 (8)
C19A—C20A—C25A—C24A177.6 (2)N1B—C9B—C10B—C11B37.3 (6)
N1X—N2B—C18B—S2B158.8 (4)C8B—C9B—C10B—C11B141.6 (4)
N1B—N2B—C18B—S2B178.0 (3)C9B—C10B—C11B—C12B179.1 (4)
N1X—N2B—C18B—S1B22.3 (5)C10B—C11B—C12B—C13B162.8 (4)
N1B—N2B—C18B—S1B0.9 (4)C10B—C11B—C12B—C17B18.4 (6)
C19B—S1B—C18B—N2B178.15 (18)C17B—C12B—C13B—C14B1.1 (9)
C19B—S1B—C18B—S2B0.70 (19)C11B—C12B—C13B—C14B180.0 (7)
C18B—S1B—C19B—C20B160.74 (18)C12B—C13B—C14B—C15B1.1 (18)
S1B—C19B—C20B—C21B93.7 (3)C13B—C14B—C15B—C16B0 (3)
S1B—C19B—C20B—C25B85.7 (3)C13B—C14B—C15B—O2B175.8 (12)
C25B—C20B—C21B—C22B2.6 (4)C27B—O2B—C15B—C16B4 (3)
C19B—C20B—C21B—C22B177.9 (2)C27B—O2B—C15B—C14B179.1 (12)
C20B—C21B—C22B—C23B0.6 (4)C14B—C15B—C16B—C17B2 (3)
C21B—C22B—C23B—C24B1.9 (4)O2B—C15B—C16B—C17B176.8 (14)
C22B—C23B—C24B—C25B2.3 (4)C15B—C16B—C17B—C12B1.9 (15)
C21B—C20B—C25B—C24B2.2 (4)C13B—C12B—C17B—C16B0.4 (8)
C19B—C20B—C25B—C24B178.4 (2)C11B—C12B—C17B—C16B178.4 (6)
C23B—C24B—C25B—C20B0.3 (4)C6X—C1X—C2X—C3X1 (5)
C9C—N1C—N2C—C18C179.3 (2)C1X—C2X—C3X—C4X1 (5)
C6C—C1C—C2C—C3C0.6 (4)C1X—C2X—C3X—O1B169 (3)
C26C—O1C—C3C—C2C20.9 (3)C26B—O1B—C3X—C2X6 (3)
C26C—O1C—C3C—C4C159.7 (2)C26B—O1B—C3X—C4X176.5 (14)
C1C—C2C—C3C—O1C178.0 (2)C2X—C3X—C4X—C5X0 (4)
C1C—C2C—C3C—C4C1.4 (4)O1B—C3X—C4X—C5X170.9 (18)
O1C—C3C—C4C—C5C177.7 (2)C3X—C4X—C5X—C6X1 (3)
C2C—C3C—C4C—C5C1.8 (4)C2X—C1X—C6X—C5X0 (4)
C3C—C4C—C5C—C6C0.1 (4)C2X—C1X—C6X—C7X175 (3)
C2C—C1C—C6C—C5C2.2 (4)C4X—C5X—C6X—C1X1 (3)
C2C—C1C—C6C—C7C175.4 (2)C4X—C5X—C6X—C7X174.5 (18)
C4C—C5C—C6C—C1C1.9 (4)C1X—C6X—C7X—C8X163.8 (19)
C4C—C5C—C6C—C7C175.6 (2)C5X—C6X—C7X—C8X12 (3)
C1C—C6C—C7C—C8C161.5 (3)C6X—C7X—C8X—C9X174.1 (14)
C5C—C6C—C7C—C8C16.0 (4)C18B—N2B—N1X—C9X177.1 (6)
C6C—C7C—C8C—C9C175.7 (2)N2B—N1X—C9X—C8X2.0 (13)
N2C—N1C—C9C—C8C0.1 (3)N2B—N1X—C9X—C10X178.1 (7)
N2C—N1C—C9C—C10C177.19 (19)C7X—C8X—C9X—N1X147.7 (13)
C7C—C8C—C9C—N1C175.7 (2)C7X—C8X—C9X—C10X32.3 (16)
C7C—C8C—C9C—C10C7.4 (3)N1X—C9X—C10X—C11X148.7 (8)
N1C—C9C—C10C—C11C26.9 (3)C8X—C9X—C10X—C11X31.4 (13)
C8C—C9C—C10C—C11C155.8 (2)C9X—C10X—C11X—C12X173.8 (7)
C9C—C10C—C11C—C12C177.1 (2)C10X—C11X—C12X—C17X153.4 (8)
C10C—C11C—C12C—C13C173.9 (2)C10X—C11X—C12X—C13X26.5 (12)
C10C—C11C—C12C—C17C7.4 (4)C17X—C12X—C13X—C14X3.0 (18)
C17C—C12C—C13C—C14C1.7 (4)C11X—C12X—C13X—C14X176.9 (14)
C11C—C12C—C13C—C14C179.6 (2)C12X—C13X—C14X—C15X0 (4)
C12C—C13C—C14C—C15C0.6 (4)C27B—O2B—C15X—C16X3 (6)
C27C—O2C—C15C—C14C2.1 (4)C27B—O2B—C15X—C14X174 (3)
C27C—O2C—C15C—C16C177.4 (3)C13X—C14X—C15X—O2B177 (2)
C13C—C14C—C15C—O2C179.5 (3)C13X—C14X—C15X—C16X4 (6)
C13C—C14C—C15C—C16C1.1 (4)O2B—C15X—C16X—C17X176 (4)
O2C—C15C—C16C—C17C178.8 (2)C14X—C15X—C16X—C17X5 (6)
C14C—C15C—C16C—C17C1.6 (4)C13X—C12X—C17X—C16X2.1 (15)
C15C—C16C—C17C—C12C0.5 (4)C11X—C12X—C17X—C16X177.8 (11)
C13C—C12C—C17C—C16C1.1 (3)C15X—C16X—C17X—C12X2 (3)
C11C—C12C—C17C—C16C179.8 (2)N2D—C18D—S1D—C19D174.9 (3)
N1C—N2C—C18C—S2C172.08 (16)S2D—C18D—S1D—C19D1.3 (3)
N1C—N2C—C18C—S1C7.0 (3)C18D—S1D—C19D—C20D162.9 (6)
C19C—S1C—C18C—N2C176.62 (17)S1D—C19D—C20D—C25D70.4 (13)
C19C—S1C—C18C—S2C4.35 (19)S1D—C19D—C20D—C21D108.5 (13)
C18C—S1C—C19C—C20C163.37 (17)C25D—C20D—C21D—C22D5 (2)
S1C—C19C—C20C—C25C67.0 (3)C19D—C20D—C21D—C22D176.0 (12)
S1C—C19C—C20C—C21C114.6 (2)C20D—C21D—C22D—C23D3 (2)
C25C—C20C—C21C—C22C0.0 (4)C21D—C22D—C23D—C24D0.0 (17)
C19C—C20C—C21C—C22C178.3 (2)C22D—C23D—C24D—C25D0.5 (15)
C20C—C21C—C22C—C23C0.2 (4)C21D—C20D—C25D—C24D4 (2)
C21C—C22C—C23C—C24C0.4 (4)C19D—C20D—C25D—C24D176.6 (11)
C22C—C23C—C24C—C25C0.3 (4)C23D—C24D—C25D—C20D1.8 (19)
C23C—C24C—C25C—C20C0.1 (4)C18D—S1Y—C19Y—C20Y130.3 (13)
C21C—C20C—C25C—C24C0.1 (4)S1Y—C19Y—C20Y—C25Y56 (3)
C19C—C20C—C25C—C24C178.2 (2)S1Y—C19Y—C20Y—C21Y135 (2)
C9D—N1D—N2D—C18D179.8 (2)C25Y—C20Y—C21Y—C22Y13 (4)
C6D—C1D—C2D—C3D1.0 (4)C19Y—C20Y—C21Y—C22Y177 (2)
C26D—O1D—C3D—C4D175.9 (3)C20Y—C21Y—C22Y—C23Y7 (4)
C26D—O1D—C3D—C2D5.0 (4)C21Y—C22Y—C23Y—C24Y1 (3)
C1D—C2D—C3D—O1D177.4 (2)C22Y—C23Y—C24Y—C25Y2 (3)
C1D—C2D—C3D—C4D1.6 (4)C21Y—C20Y—C25Y—C24Y14 (4)
O1D—C3D—C4D—C5D178.4 (2)C19Y—C20Y—C25Y—C24Y177 (2)
C2D—C3D—C4D—C5D0.8 (4)C23Y—C24Y—C25Y—C20Y8 (4)
C3D—C4D—C5D—C6D0.8 (4)
Hydrogen-bond geometry (Å, º) top
Cg1, Cg2 and Cg3 are the centroids of the C12B–C17B, C12C–C17C and C1B–C6B rings, respectively.
D—H···AD—HH···AD···AD—H···A
C24A—H24A···O2B0.932.573.262 (3)131
C21A—H21A···O1C0.932.403.249 (3)152
C21B—H21B···O1Bi0.932.333.240 (4)167
N2C—H3N2···S2Cii0.91 (4)2.53 (4)3.435 (2)179 (3)
C17C—H17C···O1Diii0.932.533.381 (3)152
N2A—H1N2···S2Aiv0.81 (3)2.69 (3)3.473 (2)161 (2)
N2B—H2N2···S2Dv0.82 (3)2.65 (3)3.461 (2)171 (3)
N2D—H4N2···S2Bv0.91 (4)2.61 (4)3.517 (2)174 (3)
C14C—H14C···Cg1iv0.932.803.558 (5)139
C16A—H16A···Cg2ii0.932.803.680 (2)158
C2D—H2DA···Cg30.932.943.700 (5)140
Symmetry codes: (i) x, y+2, z; (ii) x+2, y, z+1; (iii) x+1, y+1, z+1; (iv) x+1, y, z+1; (v) x+1, y+2, z.
Selected torsion angles (°) in the four molecules of (I) top
Torsion angles for the minor disorder component were omitted.
MoleculeτABCD
C2—C3—O1—C26τ1-2.8 (4)-7.3 (15)20.9 (3)5.0 (4)
C9—N1—N2—C18τ7-178.1 (2)-175.6 (4)-179.3 (2)179.7 (2)
C5—C6—C7—C8τ25.9 (4)16.4 (13)15.9 (4)-9.3 (4)
N1—N2—C18—S1τ8175.76 (16)-0.9 (3)6.9 (3)2.6 (3)
N1—C9—C8—C7τ3175.0 (2)147.4 (6)-175.7 (2)-156.8 (2)
N2—C18—S1—C19τ9179.43 (17)-178.15 (17)-176.64 (17)-174.9 (3)
N1—C9—C10—C11τ4-37.5 (3)-37.4 (7)-26.9 (3)-15.3 (3)
S1—C19—C20—C21τ10160.53 (17)-160.75 (17)-163.36 (16)-162.9 (6)
C17—C12—C11—C10τ519.6 (4)-18.4 (7)7.5 (3)15.9 (3)
S1—C19—C20—C21τ11-97.0 (2)93.7 (3)-114.6 (2)-108.6 (12)
C16—C15—O2—C27τ6-0.9 (4)4.1 (16)177.5 (3)177.9 (2)
Selected dihedral angles (°) top
Dihedral angle 1 is the dihedral angle between the mean planes of the 4-methoxyphenyl rings; dihedral angle 2 is the dihedral angle between the mean planes of the benzyl (C20–C25) and 4-methoxyphenyl (C1–C6) rings; dihedral angle 3 is the dihedral angle between the mean planes of the benzyl (C20–C25) and the 4-methoxyphenyl (C12–C17) rings.
MoleculeDihedral angle 1Dihedral angle 2Dihedral angle 3
A56.72 (11)85.02 (11)72.11 (2)
B89.6 (5)31.6 (5)64.9 (3)
C23.59 (12)84.46 (12)86.00 (13)
D60.82 (12)36.6 (8)89.9 (8)
Torsion angles τ7, τ8, τ9, τ10 and τ11 (°) in related hydrazinecarbodithioates top
Two sets of torsion angles are stated for compounds EXINAB, QORJAK, SIMMUX, VOJGUX and WUPGIX because there are two molecules in their asymmetric units. The molecule with disorder in the structure of compound ZENLIN was omitted from this table.
CompoundR1τ7τ8τ9τ10τ11
ABOROA (Manan et al., 2011)5-fluoro-2-oxo-1,2-dihydro-3H-indol-3-ylidenyl175.15.0-176.8168.2-98.3
ABORUG (Manan et al., 2011)5-bromo-2-oxo-1,2-dihydro-3H-indol-3-ylidenyl-178.5-9.1176.9-108.0-84.1
ABOSAN (Manan et al., 2011)5-chloro-2-oxo-1,2-dihydro-3H-indol-3-ylidenyl-178.8-7.7177.5-110.4-81.8
BAHWIT (Md Yusof et al., 2015)2-methoxybenzylidenyl-179.12.6-178.0-177.7-85.7
BAHWOZ (Md Yusof et al., 2015)3-methoxybenzylidenyl-178.0-1.2-178.1173.8-80.1
CEFBIB (Islam et al., 2016a)2,4,5-trimethoxybenzylidenyl179.6-5.2-177.9173.4-79.7
COBQUH (Mirza et al., 2014)pyridin-2-ylmethylenyl-177.2-5.3-177.2-176.0-68.7
DATFEK (Khoo et al., 2005)furan-2-yl)ethylidenyl178.61.7180.0180.0-72.5
EDETUD (How et al., 2007)1-(3-pyridyl)ethylidenyl-179.24.9-179.8-165.8-87.5
EHIXUQ (Yusof et al., 2016)2-hydroxy-3-methoxybenzylidenyl177.41.8179.9-173.3-101.2
EMEBAA (Ravoof et al., 2011)bis(pyridin-2-yl)methylenyl-165.71.4175.4176.2-83.4
EPOFAR (Ali et al., 2011)2-oxo-1,2-dihydro-3H-indol-3-ylidenyl176.5-4.5-176.2165.0-95.5
EVITUZ (Shan et al., 2011a)2-nitrobenzylidenyl170.63.6179.4-80.1132.1
EXINAB (Shan et al., 2011b)2-methylbenzylidenyl-174.0, -176.9-2.7, -4.9-178.7, -177.4174.2, 175.6-68.2, -68.7
GUMJUV (Break et al., 2013)4-chlorophenyl)ethylidenyl-172.7-0.3-179.386.868.1
HELZIK (Omar et al., 2018)1-(6-methylpyridin-2-yl)ethylidenyl-177.7-1.6-176.0171.6-108.0
IFUTUZ (Khaledi et al., 2008a)1H-indol-3-ylmethylidenyl-172.72.6179.0103.7-68.2
JAMMOA (Ali et al., 2004)quinolinyl-2-methylenyl177.90.8177.5-171.0101.8
KAGZOK (Ravoof et al., 2015)1-(5-methylpyridin-2-yl)ethylidenyl-176.9-5.6-173.2164.7-77.8
KUCRAC (Hamid et al., 2009)1-(pyrazin-2-yl)ethylidenyl178.40.6178.8174.7-70.0
KUCZUD (Xu et al., 1991)pyridine-N-oxide-2-yl)methylidenyl-171.4-2.0176.5-161.7-92.2
LOBSEB (Shan et al., 2008b)furan-2-ylmethylenyl173.8-0.5179.7177.1-93.0
LOBVOO (Tarafder et al., 2008)(E)-3-phenylallylidenyl-177.43.0177.6-175.3-102.7
LOJBUI (Khaledi et al., 2008b)1-methyl-1H-indol-2-ylmethylenyl179.1-2.3-179.1172.9-78.9
LOJLIG (Khaledi et al., 2008b)diphenylmethylenyl170.5-1.2-175.2164.8-83.8
LUBNIH (Zangrando et al., 2015)1-(3-hydroxyphenyl)ethylidenyl-177.5-0.8173.7180.0-71.1
NIZBUV (Omar et al., 2014)1-(4-methylpyridin-2-yl)ethylidenyl-178.40.0-175.8-95.9-141.1
OQOWOH (Akbar Ali et al., 2011)bis(pyridin-2-yl)methylenyl165.11.9-177.2-180.0-83.8
PEWLEL (Li et al., 2012)phenyl(pyridin-2-yl)methylenyl-177.04.6-173.187.6-119.2
QORJAK (Tan et al., 2015)3,4-dimethoxybenzylidenyl169.2, -170.4-3.1, 3.7-179.5, 175.1169.5, -168.8-118.8, -105.7
QUCLIL (Biswal et al., 2015)1-(2-hydroxyphenyl)ethylidene2-hydroxyphenyl)ethylidenyl176.70.6-173.3171.2-115.5
RIYZOP (Shan et al., 2008a)benzylidenyl177.10.1178.5171.8-80.0
RUGLAH (Li et al., 2009)3-nitrobenzylidenyl178.3-2.9-177.5173.1-85.5
SALSEE (Zhang et al., 2004)4-((2-hydroxyethyl)methylamino)benzylidenyl-166.40.9-176.8170.4-88.4
SIMMUX (Qiu & Luo, 2007)2-bromobenzylidenyl175.6, -173.92.6, -5.6178.8, -176.3-170.6, 173.6-115.6, 75.2
TADVEC (Islam et al., 2016b)3,4,5-trimethoxybenzylidenyl-179.4-5.1-177.1174.9-73.3
TIFSEH (Roy et al., 2007)2-methylthio-6-methyl-4-pyrimidyl)methylenyl-177.80.6-178.4164.9-76.6
UWATOD (Flörke & Boshaala, 2016)1-phenylethylidenyl172.4-4.0-173.3159.5-102.0
VOJCUT (Khaledi et al., 2008c)1-methyl-1H-indol-3-ylmethylidenyl-177.2-1.7-176.0-101.3-129.4
VOJGUX (Shi et al., 2008)2-chlorobenzylidenyl-174.7, 178.3-2.0, 0.3-179.3, 176.9-174.0, -174.1-80.3, -110.1
WADGAK (Chan et al., 2003)1-(thiophen-2-yl)ethylidenyl174.8-5.8177.877.617.1
WUPGIX (Tarafder et al., 2002)5-methylfuran-2-yl)methylenyl-169.2, 179.8-0.2, 1.5179.7, -176.3-173.6, -171.7-100.8, -77.9
YAHDAO (Fan et al., 2011a)4-methoxybenzylidenyl-175.81.4-179.5-178.9-87.9
YAHDUI (Fan et al., 2011b)2-bromo-5-methoxybenzylidenyl177.8-3.6-176.0174.9119.2
ZENLIN (Fun et al., 1995)4-(dimethylamino)benzylidenyl-180.01.3179.9-178.0-97.1
 

Funding information

We thank the Universiti Putra Malaysia for the use of their facilities and the University of Anbar, Ministry of Higher Education, in Iraq for a scholarship (NAT). This research was funded by the UPM under the Research University Grant Scheme (RUGS No. 05–01-11–1234RU).

References

First citationAkbar Ali, M., Mirza, A. H., Butcher, R. J., Bernhardt, P. V. & Karim, M. R. (2011). Polyhedron, 30, 1478–1486.  Web of Science CSD CrossRef CAS Google Scholar
First citationAli, M. A., Mirza, A. H., Bakar, H. J. H. A. & Bernhardt, P. V. (2011). Polyhedron, 30, 556–564.  Web of Science CSD CrossRef CAS Google Scholar
First citationAli, M. A., Mirza, A. H., Hamid, M. H. S. A., Bujang, F. H. & Bernhardt, P. V. (2004). Polyhedron, 23, 2405–2412.  Web of Science CSD CrossRef CAS Google Scholar
First citationAli, M. A. & Tarafder, M. T. H. (1977). J. Inorg. Nucl. Chem. 39, 1785–1791.  Google Scholar
First citationBasha, M. T., Chartres, J. D., Pantarat, N., Akbar Ali, M., Mirza, A. H., Kalinowski, D. S., Richardson, D. R. & Bernhardt, P. V. (2012). Dalton Trans. 41, 6536–6548.  Web of Science CSD CrossRef CAS PubMed Google Scholar
First citationBiswal, D., Pramanik, N. R., Chakrabarti, S., Chakraborty, N., Acharya, K., Mandal, S. S., Ghosh, S., Drew, M. G. B., Mondal, T. K. & Biswas, S. (2015). New J. Chem. 39, 2778–2794.  Web of Science CSD CrossRef CAS Google Scholar
First citationBreak, M. K., Tahir, M. I. M., Crouse, K. A. & Khoo, T.-J. (2013). Bioinorg. Chem. Appl. 2013, 362513.  Web of Science CSD CrossRef PubMed Google Scholar
First citationCentore, R., Takjoo, R., Capobianco, A. & Peluso, A. (2013). Inorg. Chim. Acta, 404, 29–33.  Web of Science CSD CrossRef CAS Google Scholar
First citationChan, M.-H. E., Crouse, K. A., Tarafder, M. T. H. & Yamin, B. M. (2003). Acta Cryst. E59, o628–o629.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationDolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationFan, Z., Huang, Y.-L., Wang, Z., Guo, H.-Q. & Shan, S. (2011a). Acta Cryst. E67, o3011.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationFan, Z., Huang, Y.-L., Wang, Z., Guo, H.-Q. & Shan, S. (2011b). Acta Cryst. E67, o3015.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationFlörke, U. & Boshaala, A. (2016). Private communication (refcode CCDC 1503552). CCDC, Cambridge, England.  Google Scholar
First citationFun, H.-K., Sivakumar, K., Yip, B.-C., Tian, Y.-P., Duan, C.-Y., Lu, Z.-L. & You, X.-Z. (1995). Acta Cryst. C51, 2080–2083.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationGroom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179.  Web of Science CrossRef IUCr Journals Google Scholar
First citationHamid, M. H. S. A., Akbar Ali, M., Mirza, A. H., Bernhardt, P. V., Moubaraki, B. & Murray, K. S. (2009). Inorg. Chim. Acta, 362, 3648–3656.  Web of Science CSD CrossRef CAS Google Scholar
First citationHamid, M. H. S. A., Said, A. N. A., Mirza, A. H., Karim, M. R., Arifuzzaman, M., Ali, M. A. & Bernhardt, P. V. (2016). Inorg. Chim. Acta, 453, 742–750.  Web of Science CSD CrossRef CAS Google Scholar
First citationHow, F. N.-F., Watkin, D. J., Crouse, K. A. & Tahir, M. I. M. (2007). Acta Cryst. E63, o3023–o3024.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationIslam, M. A. A. A. A., Sheikh, M. C., Mahmud, A. A., Miyatake, R. & Zangrando, E. (2016b). IUCrData, 1, x160190.  Google Scholar
First citationIslam, M. A.-A.-A.-A., Sheikh, M. C., Mumit, M. A., Miyatake, R., Alam, M. A. & Mondal, M. O. A. (2016a). J. Coord. Chem. 69, 3580–3592.  Web of Science CSD CrossRef CAS Google Scholar
First citationKhaledi, H., Mohd Ali, H. & Ng, S. W. (2008a). Acta Cryst. E64, o2107.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationKhaledi, H., Mohd Ali, H. & Ng, S. W. (2008b). Acta Cryst. E64, o2430.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationKhaledi, H., Mohd Ali, H. & Ng, S. W. (2008c). Acta Cryst. E64, o2482.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationKhoo, T.-J., Cowley, A. R., Watkin, D. J., Crouse, K. A. & Tarafder, M. T. H. (2005). Acta Cryst. E61, o2441–o2443.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationLi, H.-Q., Luo, Y., Qin, X. & Zhu, H.-L. (2009). Acta Cryst. E65, o3080.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationLi, M. X., Zhang, L. Z., Chen, C. L., Niu, J. Y. & Ji, B. S. (2012). J. Inorg. Biochem. 106, 117–125.  Web of Science CSD CrossRef CAS PubMed Google Scholar
First citationLow, M. L., Maigre, L., Tahir, M. I. M., Tiekink, E. R. T., Dorlet, P., Guillot, R., Ravoof, T. B., Rosli, R., Pagès, J., Policar, C., Delsuc, N. & Crouse, K. A. (2016). Eur. J. Med. Chem. 120, 1–12.  Web of Science CSD CrossRef CAS PubMed Google Scholar
First citationMacrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationMahapatra, D. K., Bharti, S. K. & Asati, V. (2017). Curr. Top. Med. Chem. 17, 3146–3169.  Web of Science CrossRef CAS PubMed Google Scholar
First citationManan, M. A. F. A., Crouse, K. A., Tahir, M. I. M., Rosli, R., How, F. N.-F., Watkin, D. J. & Slawin, A. M. Z. (2011). J. Chem. Crystallogr. 41, 1630–1641.  Web of Science CSD CrossRef Google Scholar
First citationMd Yusof, E. N., Ravoof, T. B. S. A., Tiekink, E. R. T., Veerakumarasivam, A., Crouse, K. A., Mohamed Tahir, M. I. & Ahmad, H. (2015). Int. J. Mol. Sci. 16, 11034–11054.  Web of Science CSD CrossRef PubMed Google Scholar
First citationMirza, A. H., Hamid, M. H. S. A., Aripin, S., Karim, M. R., Arifuzzaman, M., Ali, M. A. & Bernhardt, P. V. (2014). Polyhedron, 74, 16–23.  Web of Science CSD CrossRef CAS Google Scholar
First citationNanjundan, N., Narayanasamy, R., Geib, S., Velmurugan, K., Nandhakumar, R., Balakumaran, M. D. & Kalaichelvan, P. T. (2016). Polyhedron, 110, 203–220.  Web of Science CSD CrossRef CAS Google Scholar
First citationOmar, S. A., Chah, C. K., Ravoof, T. B. S. A., Jotani, M. M. & Tiekink, E. R. T. (2018). Acta Cryst. E74, 261–266.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationOmar, S. A., Ravoof, T. B. S. A., Tahir, M. I. M. & Crouse, K. A. (2014). Transition Met. Chem. 39, 119–126.  Web of Science CSD CrossRef CAS Google Scholar
First citationQiu, X.-Y. & Luo, Z.-G. (2007). Acta Cryst. E63, o4339.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationRavoof, T. B. S. A., Crouse, K. A., Tahir, M. I. M., How, F. N. F., Rosli, R. & Watkins, D. J. (2010). Transition Met. Chem. 35, 871–876.  Web of Science CSD CrossRef CAS Google Scholar
First citationRavoof, T. B. S. A., Crouse, K. A., Tahir, M. I. M., Rosli, R., Watkin, D. J. & How, F. N. F. (2011). J. Chem. Crystallogr. 41, 491–495.  Web of Science CSD CrossRef CAS Google Scholar
First citationRavoof, T. B. S. A., Tiekink, E. R. T., Omar, S. A., Begum, S. Z. & Tahir, M. I. M. (2015). Acta Cryst. E71, o1071–o1072.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationRigaku OD (2018). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.  Google Scholar
First citationRoy, S., Mandal, T. N., Barik, A. K., Pal, S., Gupta, S., Hazra, A., Butcher, R. J., Hunter, A. D., Zeller, M. & Kar, S. K. (2007). Polyhedron, 26, 2603–2611.  Web of Science CSD CrossRef CAS Google Scholar
First citationShan, S., Huang, Y.-L., Guo, H.-Q., Li, D.-F. & Sun, J. (2011a). Acta Cryst. E67, o2107.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationShan, S., Tian, Y.-L., Wang, S.-H., Wang, W.-L. & Xu, Y.-L. (2008a). Acta Cryst. E64, o1014.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationShan, S., Tian, Y.-L., Wang, S.-H., Wang, W.-L. & Xu, Y.-L. (2008b). Acta Cryst. E64, o1024.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationShan, S., Wang, Z., Huang, Y.-L., Guo, H.-Q. & Li, D.-F. (2011b). Acta Cryst. E67, o2497.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSheldrick, G. M. (2015). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
First citationShi, Z.-Q., Ji, N.-N. & Ji, Q.-Q. (2008). Acta Cryst. E64, o2249.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationTakjoo, R., Hayatolgheibi, S. S. & Rudbari, A. (2016). Inorg. Chim. Acta, 447, 52–58.  Web of Science CSD CrossRef CAS Google Scholar
First citationTan, Y.-F., Break, M. K., Tahir, M. I. M. bin & Khoo, T.-J. (2015). Acta Cryst. E71, 238–240.  Google Scholar
First citationTarafder, M. T. H., Crouse, K. A., Islam, M. T., Chantrapromma, S. & Fun, H.-K. (2008). Acta Cryst. E64, o1042–o1043.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationTarafder, M. T. H., Khoo, T.-J., Crouse, K. A., Ali, A. M., Yamin, B. M. & Fun, H. K. (2002). Polyhedron, 21, 2691–2698.  Web of Science CSD CrossRef CAS Google Scholar
First citationVijayan, P., Viswanathamurthi, P., Sugumar, P., Ponnuswamy, M. N., Balakumaran, M. D., Kalaichelvan, P. T., Velmurugan, K., Nandhakumar, R. & Butcher, R. J. (2015). Inorg. Chem. Front. 2, 620–639.  Web of Science CSD CrossRef CAS Google Scholar
First citationXu, Z., Alyea, E. C., Ferguson, G. & Jennings, M. C. (1991). Polyhedron, 10, 1625–1629.  CSD CrossRef CAS Web of Science Google Scholar
First citationYusof, E. N. M., Jotani, M. M., Tiekink, E. R. T. & Ravoof, T. B. S. A. (2016). Acta Cryst. E72, 516–521.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationYusof, E. N. M., Ravoof, T. B. S. A., Tahir, M. I. M., Jotani, M. M. & Tiekink, E. R. T. (2017b). Acta Cryst. E73, 397–402.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationYusof, E. N. M., Tahir, M. I. M., Ravoof, T. B. S. A., Tan, S. L. & Tiekink, E. R. T. (2017a). Acta Cryst. E73, 543–549.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationZangrando, E., Islam, M. T., Islam, M. A.-A. A. A., Sheikh, M. C., Tarafder, M. T. H., Miyatake, R., Zahan, R. & Hossain, M. A. (2015). Inorg. Chim. Acta, 427, 278–284.  Web of Science CSD CrossRef CAS Google Scholar
First citationZhang, M.-L., Tian, Y.-P., Zhang, X.-J., Wu, J.-Y., Zhang, S.-Y., Wang, D., Jiang, M.-H., Chantrapromm, S. & Fun, H.-K. (2004). Transition Met. Chem. 29, 596–602.  Web of Science CSD CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds