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Structure of the mercury(II) mixed-halide (Br/Cl) complex of 2,2′-(5-tert-butyl-1,3-phenyl­ene)bis­­(1-pentyl-1H-benzo[d]imidazole)

aDepartment of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400 076, India, and bDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
*Correspondence e-mail: rbutcher99@yahoo.com

Edited by M. Zeller, Purdue University, USA (Received 1 February 2017; accepted 9 February 2017; online 21 February 2017)

The mercury(II) complex of 2,2′-(5-tert-butyl-1,3-phenyl­ene)bis­(1-pentyl-1H-benz­imidazole), namely catena-poly[[dihalogenido­mercury(II)]-μ-2,2′-(5-tert-butyl-1,3-phenyl­ene)bis­(1-pentyl-1H-benzimidazole)-κ2N3:N3′], [HgBr1.52Cl0.48(C34H42N4)], 2, has a polymeric structure bridging via the N atoms from the benzimidazole moieties of the ligand. The compound crystallizes in the ortho­rhom­bic space group Pca21 and is a racemic twin [BASF = 0.402 (9)]. The geometry around the HgII atom is distorted tetra­hedral, with the HgII atom coordinated to two N atoms, one Br atom, and a fourth coordination site is occupied by a mixed halide (Br/Cl). For the two ligands in the asymmetric unit, there is disorder with one of the two tert-butyl groups and benzimidazole moieties showing twofold disorder, with occupancy factors of 0.57 (2):0.43 (2) for the tert-butyl group and 0.73 (3):0.27 (3) for the benzimidazole group. In addition, there is threefold disorder for two of the four n-pentyl groups, with occupancy factors of 0.669 (4):0.177 (4):0.154 (4) and 0.662 (4):0.224 (4):0.154 (4), respectively. The mol­ecules form a one-dimensional helical polymer propagating in the b-axis direction. The helices are held together by intra-strand C—H⋯Br and C—H⋯Cl inter­actions. Each strand is further linked by inter-strand C—H⋯Br and C—H⋯Cl inter­actions. In addition, there are weak C—H⋯N inter-strand inter­actions which further stabilize the structural arrangement.

1. Chemical context

During the past few years, metallated complexes of 1,3-bis­(1H-benzimidazol-2-yl)benzene ligand have been well explored. This ligand is an ideal candidate for metalation due to the presence of two N atoms and one C atom which bind tightly with metal atoms (Carina et al., 1997[Carina, R. F., Williams, A. F. & Bernardinelli, G. (1997). J. Organomet. Chem. 548, 45-48.]; Obara et al., 2006[Obara, S., Itabashi, M., Okuda, F., Tamaki, S., Tanabe, Y., Ishii, Y., Nozaki, K. & Haga, M. (2006). Inorg. Chem. 45, 8907-8921.]; Karlsson et al., 2011[Karlsson, E. A., Lee, B., Åkermark, T., Johnston, E. V., Kärkäs, M. D., Sun, J., Hansson, Ö., Bäckvall, J. & Åkermark, B. (2011). Angew. Chem. Int. Ed. 50, 11715-11718.]; Yang et al., 2012[Yang, W. W., Zhong, Y. W., Yoshikawa, S., Shao, J. Y., Masaoka, S., Sakai, K., Yao, J. & Haga, M. (2012). Inorg. Chem. 51, 890-899.]; Tam et al., 2012[Tam, A. Y. Y., Tsang, D. P. K., Chan, M. Y., Zhu, N. & Yam, V. W. W. (2012). Chem. Commun. 47, 3383-3385.]; Gonzalez, 2014[Gonzalez, A. D. (2014). Organometallics, 33, 868-875.]). A highly phospho­rescent iridium complex has been reported with the bis­(benzimidazol-2-yl)benzene ligand (Obara et al., 2006[Obara, S., Itabashi, M., Okuda, F., Tamaki, S., Tanabe, Y., Ishii, Y., Nozaki, K. & Haga, M. (2006). Inorg. Chem. 45, 8907-8921.]). Helical and nonhelical copper(I) complexes with bis­(benzimidazol-2-yl)benzene have been reported (Rüttimann et al., 1992[Rüttimann, S., Piguet, C., Bernardinelli, G., Bocquet, B. & Williams, A. F. (1992). J. Am. Chem. Soc. 114, 4230-4237.]). A trimeric complex has been obtained through the self assembly of cyclo­metalated trinuclear palladium(II) complexes (Rüttimann et al., 1993[Rüttimann, S., Bernardinelli, G. & Williams, A. F. (1993). Angew. Chem. Int. Ed. 32, 392-394.]). Dinuclear zinc complexes containing (benzimidazol-2-yl)ben­zene based ligands have shown anti­cancer activities (Xie et al., 2014[Xie, Q., Liu, S., Li, X., Wu, Q., Luo, Z., Fu, X., Cao, W., Lan, G., Li, D., Zheng, W. & Chen, T. (2014). Dalton Trans. 43, 6973-6976.]).

A literature survey of mercury halide complexes with benzimidazole derivatives has shown that they come in two main types: polymeric, bridging either through the halide (Zhang et al., 2015[Zhang, Z., Feng, Y.-F., Wei, Q.-Y., Hu, K., Chen, Z.-L. & Liang, F.-P. (2015). CrystEngComm, 17, 6724-6735.]; Li et al., 2007[Li, X.-P., Zhang, J.-Y., Liu, Y., Pan, M., Zheng, S.-R., Kang, B.-S. & Cheng-Yong Su, C.-Y. (2007). Inorg. Chim. Acta, 360, 2990-2996.]; Shen et al., 2005[Shen, Y.-H., Liu, J.-G. & Xu, D.-J. (2005). Acta Cryst. E61, m1880-m1882.]) or through alternative N atoms from the benzimidazole moieties (Xiao et al., 2009[Xiao, B., Li, W., Hou, H. & Fan, Y. (2009). J. Coord. Chem. 62, 1630-1637.], 2011[Xiao, B., Yang, L.-J., Xiao, H.-Y. & Fang, S.-M. (2011). J. Coord. Chem. 64, 4408-4420.]; Huang et al., 2006[Huang, M., Liu, P., Chen, Y., Wang, J. & Liu, Z. (2006). J. Mol. Struct. 788, 211-217.]; Li et al., 2007[Li, X.-P., Zhang, J.-Y., Liu, Y., Pan, M., Zheng, S.-R., Kang, B.-S. & Cheng-Yong Su, C.-Y. (2007). Inorg. Chim. Acta, 360, 2990-2996.], 2012a[Li, Y., Liu, Q.-K., Ma, J.-P. & Dong, Y.-B. (2012a). Acta Cryst. C68, m152-m155.],b[Li, J., Li, X., Lu, H., Zhu, Y., Sun, H., Guo, Y., Yue, Z., Zhao, J., Tang, M., Hou, H., Fan, Y. & Chang, J. (2012b). Inorg. Chim. Acta, 384, 163-169.]; Dey et al., 2013[Dey, A., Mandal, S. K. & Biradha, K. (2013). CrystEngComm, 15, 9769-9778.]; Du et al., 2011[Du, J.-L., Wei, Z.-Z. & Hu, T.-L. (2011). Solid State Sci. 13, 1256-1260.]; Chen et al., 2013[Chen, Y., Chen, C., Chen, H., Cao, T., Yue, Z., Liu, X. & Niu, Y. (2013). Synth. React. Inorg. Met.-Org. Nano-Met. Chem. 43, 1307-1310.]; Su et al., 2003[Su, C.-Y., Goforth, A. M., Smith, M. D. & zur Loye, H.-C. (2003). Inorg. Chem. 42, 5685-5692.]; Xu et al., 2011[Xu, C., Wang, X., Ding, D., Hou, H. & Fan, Y. (2011). Inorg. Chem. Commun. 14, 1410-1413.]), or as discrete mol­ecules (i.e. non-polymeric). A structurally related complex has been presented recently (Rani et al., 2017[Rani, V., Singh, H. B. & Butcher, R. J. (2017). Acta Cryst. E73, 341-344.]).

[Scheme 1]

In an attempt to synthesize bis­[4-tert-butyl-2,6-bis­(1-pentyl-1H-benzimidazol-2-yl)phen­yl]mercury (3) from [4-tert-butyl-2,6-bis­(1-pentyl-1H-benzimidazol-2-yl)phen­yl]mercury(II) chlor­ide (C34H41N4HgCl), 1, and tetra-n-butyl­ammonium bromide (Bu4N+Cl) in dry acetone, the mercury complex of 2,2′-(5-tert-butyl-1,3-phenyl­ene)bis­(1-pentyl-1H-benzimidazole) [HgBr1.52Cl0.48(C34H42N4)], 2, was isolated unexpectedly (Fig. 1[link]). The procedure for the synthesis of complex 1 will be reported elsewhere.

[Figure 1]
Figure 1
Diagram showing the starting compound, 1, the title compound, 2, and the expected product, 3.

2. Structural commentary

The title compound crystallizes in the ortho­rhom­bic space group Pca21 and is a racemic twin [BASF = 0.402 (9)]. The geometry around the HgII atom is distorted tetra­hedral with the HgII atom coordinated to two N atoms, one Br atom, and a fourth coordination site is occupied by a mixed halide (Br/Cl). There are two such sites in the asymmetric unit and in one site, the Br/Cl occupancy is 0.599 (9):0.401 (9) and in the other site the ratio is 0.431 (9):0.569 (9), giving an overall composition (L)2HgBr1.52Cl0.48, where L is 2,2′-(5-tert-butyl-1,3-phenyl­ene)bis­(1-pentyl-1H-benzimidazole). Unlike the case with the recently published structure (Rani et al., 2017[Rani, V., Singh, H. B. & Butcher, R. J. (2017). Acta Cryst. E73, 341-344.]) of a related ligand where both coordinating positions are blocked by substituents (Br and tert-but­yl), even though in the present ligand one position is open for the formation of an Hg—C bond, the basic arrangement is the same as in the previous structure.

For the two ligands in the asymmetric unit, there is considerable disorder, with one of the two tert-butyl groups and benzimidazole moieties showing twofold disorder, with occupancy factors of 0.57 (2):0.43 (2) for the tert-butyl group and 0.73 (3):0.27 (3) for the benzimidazole group. In addition, there is threefold disorder for two of the four n-pentyl groups, with occupancy factors of 0.669 (4):0.177 (4):0.154 (4) and 0.662 (4):0.224 (4):0.154 (4), respectively, as shown in Fig. 2[link]. The two sets of Hg—N bond lengths are 2.313 (7)/2.343 (6) and 2.316 (6)/2.327 (6) Å, which span a wider range than that observed (Rani et al., 2017[Rani, V., Singh, H. B. & Butcher, R. J. (2017). Acta Cryst. E73, 341-344.]) in a structurally similar complex [2.333 (4)–2.338 (4) Å]. The two sets of Hg—Cl and Hg—Br bond lengths are 2.37 (2)/2.48 (4) (the larger s.u. values are due to the disorder of the anions) and 2.508 (1)/2.593 (4) and 2.515 (1)/2.57 (2) Å, respectively. As mentioned above, the coordination environments are distorted tetra­hedral for both HgII atoms, with bond angles ranging from 97.2 (2) to 124.1 (7)°, values that are more distorted than those found in the analogous complex [100.6 (1)–126.35 (7)°] due to the disorder in the anions.

[Figure 2]
Figure 2
Diagram showing the contents of the asymmetric unit and the disorder in the various moieties. Atomic displacement parameters are shown at the 30% probability level.

The discussion of the conformations adopted by the ligand will be restricted to just those of the major components for the disordered moieties where the ligand has adopted a conformation where the two sets of two benzimidazole moieties are not coplanar with each other or their central arene ring. The dihedral angles between the two sets of benzimidazole moieties are 76.4 (3) and 88.0 (2)° (Table 1[link]), while their dihedral angles with the central ring are 60.1 (3)/59.5 (3) and 50.1 (3)/60.2 (2)°. These values are significantly different from those observed in the related complex (Rani et al., 2017[Rani, V., Singh, H. B. & Butcher, R. J. (2017). Acta Cryst. E73, 341-344.]), where the corresponding angles are 54.9 (6) and 65.6 (4)° between the two benzimidazole moieties (two values due to the disorder of one of these moieties) and 55.6 (1) and 89.3 (5)/79.2 (5)° with the central ring. Further, the four pentyl side chains have adopted quite different conformations. This can be seen by examining the dihedral angles of the C atoms in each of these groups. There are four such angles for each, C(from the planar benzimidazole ring)—N—C—C, N—C—C—C, C—C—C—C, and C—C—C—C (last C is a terminal CH3 group). The four sets of values are −115.6 (11)/−166.7 (11)/76.2 (19)/67.5 (19), 102.2 (12)/−61.5 (15)/−171.9 (13)/173.0 (16)°, 113.4 (10)/162.5 (9)/−174.7 (10)/−179.5 (11) and −104.2 (15)/−172.4 (13)/−78.2 (15)/177.1 (17)°. From these values it can be seen that the first two pentyl groups have adopted a slightly curled-up conformation, while the last two are in a fully extended all-trans conformation (Fig. 3[link]).

Table 1
Selected geometric parameters (Å, °)

Hg1—N1A 2.313 (7) Hg2—N3Ai 2.316 (6)
Hg1—N1B 2.343 (6) Hg2—N3B 2.327 (6)
Hg1—Cl11 2.373 (19) Hg2—Cl21 2.48 (4)
Hg1—Br12 2.5083 (10) Hg2—Br22 2.5147 (11)
Hg1—Br11 2.593 (4) Hg2—Br21 2.57 (2)
       
N1A—Hg1—N1B 99.4 (3) N3Ai—Hg2—N3B 97.2 (2)
N1A—Hg1—Cl11 107.1 (6) N3Ai—Hg2—Cl21 101.7 (8)
N1B—Hg1—Cl11 108.0 (5) N3B—Hg2—Cl21 105.0 (9)
N1A—Hg1—Br12 115.82 (18) N3Ai—Hg2—Br22 115.13 (18)
N1B—Hg1—Br12 111.26 (17) N3B—Hg2—Br22 109.95 (17)
Cl11—Hg1—Br12 114.1 (5) Cl21—Hg2—Br22 124.1 (7)
N1A—Hg1—Br11 103.9 (2) N3Ai—Hg2—Br21 105.3 (5)
N1B—Hg1—Br11 105.2 (2) N3B—Hg2—Br21 107.8 (5)
Br12—Hg1—Br11 119.01 (12) Br22—Hg2—Br21 119.1 (4)
Symmetry code: (i) x, y-1, z.
[Figure 3]
Figure 3
Diagram containing two units of the polymer illustrating its zigzag nature, with H atoms omitted for clarity (symmetry code for generating the second unit: x, y − 1, z). Minor components of both the pentyl and benzimidazole disorder, as well as the chloride-anion disorder, have been omitted for clarity. H atoms have also been omitted for clarity. Atomic displacement parameters are shown at the 30% probability level.

3. Supra­molecular features

The mol­ecules form a one-dimensional helical polymer pro­pagating in the b direction (Fig. 4[link]). The helices are held together by intra-strand C—H⋯Br and C—H⋯Cl inter­actions. Each strand is further linked by inter-strand C—H⋯Br and C—H⋯Cl inter­actions. There are inter-strand ππ inter­actions between the benzimidazole moieties which help stabilize the packing [N1B/N2B/C1B/C2B/C7B⋯C24A–C29A (symmetry code: [{1\over 2}] + x, 1 − y, z) and N3A/N4A/C23A/C24A/C29A⋯C2B–C7B (symmetry code: x − [{1\over 2}], 1 − y, z]. In addition, there are weak C—H⋯N inter­actions which further stabilize the structural arrangement. Numerical details are given in Table 2[link].

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C3A—H3AA⋯N1B 0.95 2.45 3.29 (4) 148
C8A—H8AB⋯Br22ii 0.99 2.94 3.873 (11) 158
C25A—H25A⋯Br21ii 0.95 2.96 3.66 (2) 131
C25A—H25A⋯Cl21ii 0.95 2.74 3.45 (3) 132
C28A—H28A⋯Br11iii 0.95 2.96 3.793 (12) 147
C28A—H28A⋯Cl11iii 0.95 2.86 3.70 (2) 149
C30A—H30B⋯Br11iii 0.99 3.04 3.979 (13) 158
C3B—H3BA⋯Br11 0.95 2.96 3.631 (11) 129
C6B—H6BA⋯Br21iv 0.95 2.88 3.75 (2) 153
C6B—H6BA⋯Cl21iv 0.95 2.89 3.73 (4) 149
C25B—H25B⋯N3Ai 0.95 2.56 3.332 (14) 139
C30D—H30G⋯Br12 0.99 3.06 3.95 (5) 150
Symmetry codes: (i) x, y-1, z; (ii) x, y+1, z; (iii) [x-{\script{1\over 2}}, -y+1, z]; (iv) [x+{\script{1\over 2}}, -y, z].
[Figure 4]
Figure 4
Packing diagram, viewed along the c axis, showing two strands of the polymer which propagate in the b-axis direction.

4. Database survey

A survey of the structural investigations of mercury halide complexes with benzimidazole derivatives has shown that they come in two main types; polymeric, bridging either through the halide (Zhang et al., 2015[Zhang, Z., Feng, Y.-F., Wei, Q.-Y., Hu, K., Chen, Z.-L. & Liang, F.-P. (2015). CrystEngComm, 17, 6724-6735.]; Li et al., 2007[Li, X.-P., Zhang, J.-Y., Liu, Y., Pan, M., Zheng, S.-R., Kang, B.-S. & Cheng-Yong Su, C.-Y. (2007). Inorg. Chim. Acta, 360, 2990-2996.]; Shen et al., 2005[Shen, Y.-H., Liu, J.-G. & Xu, D.-J. (2005). Acta Cryst. E61, m1880-m1882.]) or through alternative N atoms from the benzimidazole moieties (Xiao et al., 2009[Xiao, B., Li, W., Hou, H. & Fan, Y. (2009). J. Coord. Chem. 62, 1630-1637.], 2011[Xiao, B., Yang, L.-J., Xiao, H.-Y. & Fang, S.-M. (2011). J. Coord. Chem. 64, 4408-4420.]; Huang et al., 2006[Huang, M., Liu, P., Chen, Y., Wang, J. & Liu, Z. (2006). J. Mol. Struct. 788, 211-217.]; Li et al., 2007[Li, X.-P., Zhang, J.-Y., Liu, Y., Pan, M., Zheng, S.-R., Kang, B.-S. & Cheng-Yong Su, C.-Y. (2007). Inorg. Chim. Acta, 360, 2990-2996.], 2012a[Li, Y., Liu, Q.-K., Ma, J.-P. & Dong, Y.-B. (2012a). Acta Cryst. C68, m152-m155.],b[Li, J., Li, X., Lu, H., Zhu, Y., Sun, H., Guo, Y., Yue, Z., Zhao, J., Tang, M., Hou, H., Fan, Y. & Chang, J. (2012b). Inorg. Chim. Acta, 384, 163-169.]; Dey et al., 2013[Dey, A., Mandal, S. K. & Biradha, K. (2013). CrystEngComm, 15, 9769-9778.]; Du et al., 2011[Du, J.-L., Wei, Z.-Z. & Hu, T.-L. (2011). Solid State Sci. 13, 1256-1260.]; Chen et al., 2013[Chen, Y., Chen, C., Chen, H., Cao, T., Yue, Z., Liu, X. & Niu, Y. (2013). Synth. React. Inorg. Met.-Org. Nano-Met. Chem. 43, 1307-1310.]; Su et al., 2003[Su, C.-Y., Goforth, A. M., Smith, M. D. & zur Loye, H.-C. (2003). Inorg. Chem. 42, 5685-5692.]; Xu et al., 2011[Xu, C., Wang, X., Ding, D., Hou, H. & Fan, Y. (2011). Inorg. Chem. Commun. 14, 1410-1413.]), or discrete mol­ecules, i.e. nonpolymeric (Xiao et al., 2011[Xiao, B., Yang, L.-J., Xiao, H.-Y. & Fang, S.-M. (2011). J. Coord. Chem. 64, 4408-4420.]; Wu et al., 2009[Wu, J., Yang, J. & Pan, F. (2009). Acta Cryst. E65, m829.]; Zhao et al., 2012[Zhao, J., Li, S., Chen, S., Bai, Y. & Hu, J. (2012). J. Coord. Chem. 65, 1201-1211.]; Lou et al., 2012[Lou, S.-F., Wang, Q. & Ding, J. (2012). Z. Kristallogr. New Cryst. Struct. 227, 105-106.]; Zhu et al., 2009[Zhu, X.-W., Xiao, B., Yin, Z.-G., Qian, H.-Y. & Li, G.-S. (2009). Acta Cryst. E65, m912.]; Carballo et al., 1993[Carballo, R., Castineiras, A., Conde, M. C. G. & Hiller, W. (1993). Polyhedron, 12, 1655-1660.]; Yan et al., 2012[Yan, S., Jin, G., Yang, Y., Su, X. & Meng, X. (2012). Synth. React. Inorg. Met.-Org. Nano-Met. Chem. 42, 678-684.]; Hu et al., 2012[Hu, J., Liao, C., Zhao, J. & Haipeng Zhao, H. (2012). Z. Kristallogr. New Cryst. Struct. 227, 69-70.], 2015[Hu, J. Y., Liao, C. L., Hu, L. L., Zhang, C. C., Chen, S. F. & Zhao, J. (2015). Russ. J. Coord. Chem. 41, 212-219.]; Ding et al., 2012[Ding, Y., Zhou, X., Jin, G., Zhao, D. & Meng, X. (2012). Synth. React. Inorg. Met.-Org. Nano-Met. Chem. 42, 438-443.]; Matthews et al., 1998[Matthews, C. J., Clegg, W., Heath, S. L., Martin, N. C., Hill, M. N. S. & Lockhart, J. C. (1998). Inorg. Chem. 37, 199-207.]; Manjunatha et al., 2011[Manjunatha, M. N., Dikundwar, A. G. & Nagasundara, K. R. (2011). Polyhedron, 30, 1299-1304.]; Wang et al., 2007[Wang, X.-F., Lv, Y., Su, Z., Okamura, T., Wu, G., Sun, W.-Y. & Ueyama, N. (2007). Z. Anorg. Allg. Chem. 633, 2695-2700.], 2009[Wang, J.-J., Yan, L.-F., Li, Z.-X., Chang, Z., Hu, T.-L. & Bu, X.-H. (2009). Inorg. Chim. Acta, 362, 3147-3154.], 2012[Wang, Q., Fu, Z.-Y. & Yu, L.-M. (2012). Acta Cryst. E68, m44.], 2015[Wang, X., Yang, H.-Y., Zhang, C., Yuan, J. & Yang, H.-X. (2015). Z. Kristallogr. New Cryst. Struct. 230, 361-362.]; Chen et al., 2014[Chen, S., Fan, R.-Q., Wang, X.-M. & Yang, Y.-L. (2014). CrystEngComm, 16, 6114-6125.]; Su et al., 2003[Su, C.-Y., Goforth, A. M., Smith, M. D. & zur Loye, H.-C. (2003). Inorg. Chem. 42, 5685-5692.]; Quiroz-Castro et al., 2000[Quiroz-Castro, E., Bernes, S., Barba-Behrens, N., Tapia-Benavides, R., Contreras, R. & Noth, H. (2000). Polyhedron, 19, 1479-1484.]; Yang & Luo, 2012[Yang, G.-Y. & Luo, L.-X. (2012). Z. Kristallogr. New Cryst. Struct. 227, 441-442.]; He et al., 2012[He, C.-J., Zu, E.-P. & Zhou, X.-J. (2012). Z. Kristallogr. New Cryst. Struct. 227, 445-446.]; Bouchouit et al., 2015[Bouchouit, M., Benzerka, S., Bouraiou, A., Merazig, H., Belfaitah, A. & Bouacida, S. (2015). Acta Cryst. E71, m253-m254.]).

5. Synthesis and crystallization

To a solution of 1 (0.5 g, 0.67 mmol) in dry acetone was added tetra-n-butyl­ammonium bromide (0.26 g, 0.82 mmol) at room temperature. The reaction mixture was refluxed for 3 h under an inert atmosphere of N2 and then filtered through Whatman filter paper. The residue contained shiny mercury particles which could be witnessed with the naked eye and the solvent was evaporated from the filtrate and washed with petroleum ether and then with diethyl ether. The compound was dried under vacuo. Colorless plate-shaped single crystals were obtained from DMSO at 291 K (yield 18%, 0.21 g). 1H NMR (500 MHz, DMSO): δ 7.96–7.93 (m, 3H), 7.74 (d, J = 7.9 Hz, 2H), 7.70 (d, J = 7.9 Hz, 2H), 7.33–7.26 (m, 4H), 4.35 (t, J = 7.4 Hz, 4H), 1.72 (m, 4H), 1.42 (s, 9 H), 1.15–0.93 (m, 8H), 0.71 (t, J = 6.8 Hz, 6H). Analysis calculated for C34H42Br1.52Cl0.48HgN4: C 48.33, H 5.01, N 6.63%; found: C 49.73, H 5.14, N 6.84%.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3[link]. The title compound was refined as a racemic twin [BASF = 0.402 (9)]. The H atoms were positioned geometrically and refined as riding, with C—H = 0.95–0.98 Å and Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) otherwise. For the two ligands in the asymmetric unit, there is considerable disorder with one of the two tert-butyl groups and benzimidazole moieties showing twofold disorder, with occupancy factors of 0.57 (2):0.43 (2) for the tert-butyl group and 0.73 (3):0.27 (3) for the benzimidazole group. The displacement parameters of the disordered tert-butyl group were restrained to be similar (SIMU command). One C atom (C22C) from the minor component was additionally restrained to be close to isotropic (ISOR 0.005 command). The two components of the benzimidazole moiety were restrained to be planar using the FLAT command and their metrical and displacement parameters were restrained using the SIMU and SADI commands in SHELXL2016 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]). In addition, there is threefold disorder (occupancies summed to unity using the SUMP command) for two of the four n-pentyl groups, with occupancy factors of 0.669 (4):0.177 (4):0.154 (4) and 0.662 (4):0.224 (4):0.154 (4), respectively. For one pentyl group, some atoms (C30A–C32A and C30C–C32C) of two of the three components were refined as overlapping (using EXYZ commands). For the other disordered pentyl group, all atoms of all three components adopt independent conformations. One of the occupancy rates (of the least prevalent moieties E and F) is shared between the two disordered sites due to mutually exclusive overlap of atoms.

Table 3
Experimental details

Crystal data
Chemical formula [HgBr1.52Cl0.48(C34H42N4)]
Mr 845.56
Crystal system, space group Orthorhombic, Pca21
Temperature (K) 100
a, b, c (Å) 22.8887 (14), 13.8830 (8), 21.1396 (12)
V3) 6717.4 (7)
Z 8
Radiation type Cu Kα
μ (mm−1) 10.90
Crystal size (mm) 0.19 × 0.17 × 0.07
 
Data collection
Diffractometer Bruker APEXII CCD
Absorption correction Multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.])
Tmin, Tmax 0.394, 0.753
No. of measured, independent and observed [I > 2σ(I)] reflections 93252, 11762, 11431
Rint 0.043
(sin θ/λ)max−1) 0.596
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.029, 0.069, 1.14
No. of reflections 11762
No. of parameters 997
No. of restraints 888
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 1.38, −0.85
Absolute structure Refined as an inversion twin
Absolute structure parameter 0.402 (9)
Computer programs: APEX2 (Bruker, 2005[Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]), SAINT (Bruker, 2002[Bruker (2002). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]), SUPERFLIP (Palatinus & Chapuis, 2007[Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.]), SHELXL2016 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]) and SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supporting information


Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

catena-Poly[[di(brimido/chlorido)mercury(II)]-µ-2,2'-(5-tert-butyl-1,3-phenylene)bis(1-pentyl-1H-benzimidazole)-κ2N3:N3'] top
Crystal data top
[HgBr1.52Cl0.48(C34H42N4)]Dx = 1.672 Mg m3
Mr = 845.56Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, Pca21Cell parameters from 9060 reflections
a = 22.8887 (14) Åθ = 3.7–66.7°
b = 13.8830 (8) ŵ = 10.90 mm1
c = 21.1396 (12) ÅT = 100 K
V = 6717.4 (7) Å3Plate, colourless
Z = 80.19 × 0.17 × 0.07 mm
F(000) = 3322
Data collection top
Bruker APEXII CCD
diffractometer
11431 reflections with I > 2σ(I)
ω scansRint = 0.043
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
θmax = 66.8°, θmin = 3.7°
Tmin = 0.394, Tmax = 0.753h = 2726
93252 measured reflectionsk = 1616
11762 independent reflectionsl = 2524
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.029 w = 1/[σ2(Fo2) + (0.0061P)2 + 31.5501P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.069(Δ/σ)max = 0.005
S = 1.14Δρmax = 1.38 e Å3
11762 reflectionsΔρmin = 0.85 e Å3
997 parametersAbsolute structure: Refined as an inversion twin
888 restraintsAbsolute structure parameter: 0.402 (9)
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*/UeqOcc. (<1)
Hg10.73599 (2)0.47092 (2)0.25318 (2)0.02440 (9)
Hg20.51919 (2)0.02075 (2)0.26809 (2)0.02425 (9)
Br120.66545 (5)0.44471 (7)0.34233 (5)0.0370 (2)
Br220.60239 (5)0.03762 (8)0.19119 (5)0.0445 (3)
Br110.83121 (16)0.5668 (4)0.2745 (3)0.0346 (9)0.599 (9)
Br210.4296 (10)0.0792 (15)0.2364 (8)0.0278 (19)0.431 (9)
Cl110.8204 (7)0.5600 (15)0.2819 (12)0.0346 (9)0.401 (9)
Cl210.4287 (19)0.072 (3)0.2464 (15)0.0278 (19)0.569 (9)
N1A0.6978 (3)0.5423 (5)0.1634 (3)0.0244 (15)
N2A0.6527 (4)0.6503 (6)0.1029 (4)0.0329 (17)
N3A0.4820 (3)0.8355 (5)0.3065 (3)0.0212 (14)
N4A0.4668 (4)0.6774 (6)0.3121 (4)0.034 (2)
C1A0.6660 (4)0.6220 (6)0.1630 (4)0.0216 (17)
C2A0.7011 (14)0.511 (3)0.1012 (13)0.032 (4)0.27 (3)
C3A0.7268 (19)0.429 (3)0.0766 (17)0.036 (4)0.27 (3)
H3AA0.7459150.3827200.1027020.044*0.27 (3)
C4A0.723 (2)0.417 (3)0.0106 (17)0.042 (4)0.27 (3)
H4AA0.7388360.3617010.0091040.051*0.27 (3)
C5A0.696 (2)0.486 (3)0.0251 (18)0.043 (4)0.27 (3)
H5AA0.6956030.4766180.0696500.052*0.27 (3)
C6A0.6696 (19)0.567 (3)0.002 (2)0.039 (4)0.27 (3)
H6AA0.6502170.6119150.0287070.047*0.27 (3)
C7A0.673 (2)0.579 (3)0.064 (2)0.035 (4)0.27 (3)
C2C0.7089 (6)0.5217 (12)0.0993 (7)0.032 (2)0.73 (3)
C3C0.7434 (8)0.4511 (14)0.0700 (7)0.036 (3)0.73 (3)
H3CA0.7643380.4053230.0944260.043*0.73 (3)
C4C0.7461 (10)0.4498 (13)0.0038 (7)0.043 (3)0.73 (3)
H4CA0.7692630.4023720.0167180.052*0.73 (3)
C5C0.7163 (9)0.5152 (14)0.0319 (7)0.044 (3)0.73 (3)
H5CA0.7178060.5105860.0766860.053*0.73 (3)
C6C0.6840 (8)0.5876 (14)0.0047 (8)0.040 (3)0.73 (3)
H6CA0.6652400.6354170.0295690.048*0.73 (3)
C7C0.6800 (8)0.5878 (12)0.0614 (8)0.036 (3)0.73 (3)
C8A0.6258 (5)0.7407 (8)0.0829 (5)0.043 (3)
H8AA0.6518680.7729890.0521580.052*
H8AB0.6217890.7835560.1201030.052*
C9A0.5670 (5)0.7270 (11)0.0533 (6)0.058 (4)
H9A10.5382390.7096850.0864290.070*
H9A20.5687840.6732800.0225630.070*
C10A0.5470 (7)0.8182 (15)0.0197 (7)0.089 (6)
H10A0.5546320.8740290.0476680.107*
H10B0.5043230.8144080.0128340.107*
C11A0.5770 (8)0.8360 (17)0.0441 (8)0.102 (8)
H11A0.5663210.9013780.0589280.122*
H11B0.6197960.8351470.0375200.122*
C12A0.5624 (7)0.7661 (18)0.0949 (7)0.103 (8)
H12A0.5199330.7587530.0976780.154*
H12B0.5802350.7036150.0851540.154*
H12C0.5775640.7897030.1354160.154*
C13A0.6456 (4)0.6727 (6)0.2197 (4)0.0258 (19)
C14A0.6867 (4)0.7111 (5)0.2622 (4)0.0249 (17)
H14A0.7272170.7015970.2545460.030*
C15A0.6689 (4)0.7630 (6)0.3156 (4)0.028 (2)
C16A0.6096 (4)0.7737 (6)0.3256 (4)0.0258 (19)
H16A0.5967730.8093240.3613390.031*
C17A0.5682 (4)0.7346 (6)0.2854 (4)0.0223 (18)
C18A0.5862 (4)0.6849 (6)0.2315 (4)0.0220 (17)
H18A0.5581020.6595520.2029110.026*
C19A0.7129 (5)0.8058 (8)0.3625 (5)0.035 (2)
C20A0.7774 (9)0.794 (2)0.3430 (11)0.056 (5)0.573 (19)
H20A0.7854220.8347130.3060630.084*0.573 (19)
H20B0.7850650.7266500.3324120.084*0.573 (19)
H20C0.8026080.8138320.3781500.084*0.573 (19)
C21A0.7029 (9)0.9158 (13)0.3683 (12)0.046 (5)0.573 (19)
H21A0.7324920.9434570.3964550.069*0.573 (19)
H21B0.6639340.9279030.3856660.069*0.573 (19)
H21C0.7060740.9455320.3263770.069*0.573 (19)
C22A0.7053 (12)0.763 (2)0.4258 (10)0.063 (6)0.573 (19)
H22A0.7103940.6933030.4233250.094*0.573 (19)
H22B0.6660240.7779470.4415710.094*0.573 (19)
H22C0.7344590.7903680.4547670.094*0.573 (19)
C20C0.7617 (16)0.848 (3)0.3303 (15)0.057 (6)0.427 (19)
H20D0.7928480.8612970.3608730.085*0.427 (19)
H20E0.7495120.9078670.3099420.085*0.427 (19)
H20F0.7761550.8028040.2981940.085*0.427 (19)
C21C0.6807 (14)0.870 (2)0.4101 (16)0.061 (7)0.427 (19)
H21D0.6506120.8328250.4318850.092*0.427 (19)
H21E0.6623110.9242450.3875470.092*0.427 (19)
H21F0.7086200.8956410.4410630.092*0.427 (19)
C22C0.7342 (11)0.717 (2)0.4038 (12)0.042 (5)0.427 (19)
H22D0.7672650.7373300.4302500.062*0.427 (19)
H22E0.7464420.6647320.3759400.062*0.427 (19)
H22F0.7021440.6953800.4309440.062*0.427 (19)
C23A0.5062 (4)0.7496 (6)0.2999 (4)0.0256 (19)
C24A0.4243 (4)0.8198 (7)0.3246 (4)0.027 (2)
C25A0.3788 (4)0.8842 (8)0.3388 (4)0.032 (2)
H25A0.3844750.9519590.3374940.038*
C26A0.3256 (4)0.8445 (8)0.3546 (5)0.036 (2)
H26A0.2939900.8859890.3648510.044*
C27A0.3170 (5)0.7458 (9)0.3560 (5)0.041 (3)
H27A0.2791360.7222550.3661220.049*
C28A0.3599 (5)0.6809 (8)0.3436 (5)0.040 (3)
H28A0.3534220.6133430.3452190.048*
C29A0.4149 (5)0.7210 (7)0.3280 (5)0.035 (2)
C30A0.4780 (6)0.5738 (7)0.3149 (5)0.047 (2)0.669 (4)
H30A0.5150770.5596810.2926990.057*0.669 (4)
H30B0.4462640.5394750.2925000.057*0.669 (4)
C31A0.4820 (7)0.5352 (9)0.3840 (6)0.048 (2)0.669 (4)
H31A0.4443010.5477790.4054300.057*0.669 (4)
H31B0.4874010.4644570.3823780.057*0.669 (4)
C32A0.5307 (6)0.5780 (9)0.4239 (6)0.050 (2)0.669 (4)
H32A0.5224510.6470200.4316020.060*0.669 (4)
H32B0.5680250.5734000.4005240.060*0.669 (4)
C33A0.5368 (10)0.5255 (14)0.4880 (8)0.054 (4)0.669 (4)
H33A0.5014210.5369330.5139710.065*0.669 (4)
H33B0.5403860.4552970.4807960.065*0.669 (4)
C34A0.5902 (9)0.5620 (18)0.5228 (10)0.069 (5)0.669 (4)
H34A0.5869610.6318410.5287970.103*0.669 (4)
H34B0.6252690.5475910.4979890.103*0.669 (4)
H34C0.5928850.5303540.5641200.103*0.669 (4)
C30C0.4780 (6)0.5738 (7)0.3149 (5)0.047 (2)0.177 (4)
H30E0.5150770.5596810.2926990.057*0.177 (4)
H30F0.4462640.5394750.2925000.057*0.177 (4)
C31C0.4820 (7)0.5352 (9)0.3840 (6)0.048 (2)0.177 (4)
H31E0.4443010.5477790.4054300.057*0.177 (4)
H31F0.4874010.4644570.3823780.057*0.177 (4)
C32C0.5307 (6)0.5780 (9)0.4239 (6)0.050 (2)0.177 (4)
H32E0.5226090.6480120.4254320.060*0.177 (4)
H32F0.5666300.5704690.3983890.060*0.177 (4)
C33C0.548 (4)0.550 (4)0.4915 (17)0.052 (4)0.177 (4)
H33E0.5806600.5917430.5060190.062*0.177 (4)
H33F0.5145930.5598250.5203910.062*0.177 (4)
C34C0.567 (3)0.447 (4)0.492 (3)0.054 (8)0.177 (4)
H34D0.5991360.4375610.4627720.080*0.177 (4)
H34E0.5337460.4060270.4797840.080*0.177 (4)
H34F0.5792780.4293410.5351560.080*0.177 (4)
C30F0.4780 (6)0.5738 (7)0.3149 (5)0.047 (2)0.154 (3)
H30K0.4999020.5534770.2768370.057*0.154 (3)
H30L0.4404350.5384980.3157080.057*0.154 (3)
C31F0.513 (2)0.550 (5)0.3741 (15)0.050 (3)0.154 (3)
H31K0.5138510.4788930.3800990.060*0.154 (3)
H31L0.5540430.5716190.3684110.060*0.154 (3)
C32F0.488 (2)0.597 (5)0.4327 (19)0.051 (4)0.154 (3)
H32K0.4829280.6669490.4252060.061*0.154 (3)
H32L0.5145040.5882020.4688910.061*0.154 (3)
C33F0.428 (3)0.552 (4)0.448 (3)0.051 (5)0.154 (3)
H33K0.4028910.5530320.4103770.061*0.154 (3)
H33L0.4333760.4845770.4617830.061*0.154 (3)
C34F0.399 (3)0.608 (6)0.501 (3)0.057 (13)0.154 (3)
H34P0.4254430.6114990.5370440.085*0.154 (3)
H34Q0.3628530.5757040.5128420.085*0.154 (3)
H34R0.3903250.6733090.4856890.085*0.154 (3)
N1B0.7667 (3)0.3243 (5)0.2096 (3)0.0223 (15)
N2B0.7794 (3)0.1645 (5)0.2095 (3)0.0224 (15)
N3B0.5535 (3)0.0389 (5)0.3640 (3)0.0190 (14)
N4B0.6096 (3)0.1219 (5)0.4286 (4)0.0270 (16)
C1B0.7416 (4)0.2388 (6)0.2209 (4)0.0203 (17)
C2B0.8237 (4)0.3043 (6)0.1898 (5)0.0248 (19)
C3B0.8688 (4)0.3664 (7)0.1718 (5)0.034 (2)
H3BA0.8632810.4341720.1703960.041*
C4B0.9215 (4)0.3251 (8)0.1564 (6)0.038 (2)
H4BA0.9530810.3657290.1445790.046*
C5B0.9302 (4)0.2248 (7)0.1574 (5)0.031 (2)
H5BA0.9672410.1991010.1460590.038*
C6B0.8858 (4)0.1637 (7)0.1747 (4)0.029 (2)
H6BA0.8915360.0959260.1760910.035*
C7B0.8320 (4)0.2045 (6)0.1902 (4)0.0211 (18)
C8B0.7685 (5)0.0613 (6)0.2132 (5)0.035 (2)
H8BA0.7293200.0506360.2318200.042*
H8BB0.7975940.0319820.2420730.042*
C9B0.7715 (5)0.0106 (7)0.1499 (5)0.044 (3)
H9BA0.8049680.0360290.1253680.052*
H9BB0.7353530.0237090.1257240.052*
C10B0.7786 (5)0.0982 (7)0.1589 (5)0.043 (2)
H10C0.8125440.1101950.1868700.051*
H10D0.7434450.1237400.1803060.051*
C11B0.7876 (6)0.1531 (9)0.0970 (6)0.055 (3)
H11C0.7538900.1413050.0687070.066*
H11D0.8231160.1285900.0756100.066*
C12B0.7939 (6)0.2601 (7)0.1078 (6)0.053 (3)
H12D0.7998730.2926170.0671560.079*
H12E0.7584320.2850000.1279230.079*
H12F0.8275760.2721750.1353540.079*
C13B0.6811 (3)0.2286 (5)0.2425 (4)0.0191 (16)
C14B0.6381 (4)0.2784 (6)0.2093 (4)0.0214 (17)
H14B0.6485350.3147120.1729010.026*
C15B0.5796 (3)0.2755 (5)0.2288 (4)0.0191 (17)
C16B0.5657 (3)0.2196 (5)0.2807 (4)0.0190 (17)
H16B0.5259570.2146100.2933450.023*
C17B0.6084 (4)0.1701 (6)0.3151 (4)0.0194 (17)
C18B0.6664 (4)0.1748 (6)0.2958 (4)0.0183 (16)
H18B0.6958550.1415620.3187790.022*
C19B0.5324 (4)0.3299 (6)0.1905 (5)0.029 (2)
C20B0.5184 (5)0.2722 (7)0.1314 (5)0.037 (2)
H20G0.4878440.3051280.1072640.056*
H20H0.5047030.2078760.1435760.056*
H20I0.5536250.2661730.1053750.056*
C21B0.5551 (4)0.4300 (6)0.1715 (5)0.034 (2)
H21G0.5236370.4665290.1512430.050*
H21H0.5877660.4228800.1418590.050*
H21I0.5684730.4644230.2093140.050*
C22B0.4769 (4)0.3428 (7)0.2295 (6)0.037 (2)
H22G0.4487560.3816740.2056050.056*
H22H0.4863590.3754250.2692950.056*
H22I0.4597990.2795600.2386310.056*
C23B0.5902 (3)0.1098 (6)0.3686 (4)0.0199 (17)
C24B0.5475 (4)0.0013 (6)0.4250 (4)0.0238 (18)
C25B0.5131 (6)0.0741 (9)0.4486 (6)0.055 (4)
H25B0.4876650.1094700.4216710.066*
C26B0.5173 (7)0.0950 (10)0.5115 (6)0.063 (4)
H26B0.4961960.1485850.5276250.075*
C27B0.5513 (5)0.0407 (8)0.5533 (5)0.042 (3)
H27B0.5514300.0555490.5971870.050*
C28B0.5844 (5)0.0337 (8)0.5310 (5)0.036 (2)
H28B0.6082540.0706150.5586370.044*
C29B0.5824 (4)0.0539 (7)0.4664 (4)0.0251 (18)
C30B0.6566 (7)0.1804 (14)0.4558 (8)0.033 (3)0.622 (4)
H30C0.6420670.2120930.4946580.039*0.622 (4)
H30D0.6673760.2314780.4252830.039*0.622 (4)
C31B0.7112 (6)0.1213 (13)0.4720 (8)0.043 (3)0.622 (4)
H31C0.6977650.0646900.4965010.051*0.622 (4)
H31D0.7268330.0963380.4315440.051*0.622 (4)
C32B0.7619 (7)0.1635 (13)0.5075 (9)0.051 (4)0.622 (4)
H32C0.7480960.1855280.5494170.062*0.622 (4)
H32D0.7762780.2206030.4841880.062*0.622 (4)
C33B0.8125 (8)0.0937 (15)0.5169 (11)0.050 (5)0.622 (4)
H33C0.7994660.0381750.5426840.060*0.622 (4)
H33D0.8258930.0691480.4754250.060*0.622 (4)
C34B0.8615 (10)0.144 (2)0.5494 (12)0.078 (6)0.622 (4)
H34G0.8931560.0976970.5572760.117*0.622 (4)
H34H0.8476780.1699810.5897240.117*0.622 (4)
H34I0.8758490.1961100.5225960.117*0.622 (4)
C30D0.6324 (19)0.225 (4)0.455 (2)0.031 (5)0.224 (4)
H30G0.6510790.2600900.4196210.037*0.224 (4)
H30H0.5983340.2626770.4691520.037*0.224 (4)
C31D0.6758 (14)0.216 (3)0.5091 (17)0.036 (4)0.224 (4)
H31G0.6616470.2603570.5427090.043*0.224 (4)
H31H0.6718880.1502420.5260460.043*0.224 (4)
C32D0.7400 (14)0.235 (3)0.502 (2)0.049 (5)0.224 (4)
H32G0.7465830.3051850.5070510.059*0.224 (4)
H32H0.7515350.2175430.4586310.059*0.224 (4)
C33D0.7810 (18)0.183 (4)0.548 (2)0.053 (5)0.224 (4)
H33G0.8027220.2309700.5732460.063*0.224 (4)
H33H0.7575150.1432070.5774750.063*0.224 (4)
C34D0.823 (3)0.120 (4)0.514 (3)0.052 (8)0.224 (4)
H34J0.8385420.0712610.5433230.078*0.224 (4)
H34K0.8555450.1590380.4978370.078*0.224 (4)
H34L0.8034660.0878310.4787460.078*0.224 (4)
C30E0.642 (3)0.213 (5)0.443 (4)0.032 (5)0.154 (3)
H30I0.6607590.2377680.4044240.038*0.154 (3)
H30J0.6729840.1996560.4747170.038*0.154 (3)
C31E0.601 (2)0.290 (3)0.470 (3)0.032 (6)0.154 (3)
H31I0.5764250.3157940.4347890.038*0.154 (3)
H31J0.5739730.2597430.5007640.038*0.154 (3)
C32E0.631 (2)0.374 (3)0.502 (3)0.036 (6)0.154 (3)
H32I0.6638170.3956210.4741980.043*0.154 (3)
H32J0.6488700.3506300.5418340.043*0.154 (3)
C33E0.592 (2)0.461 (4)0.516 (3)0.048 (5)0.154 (3)
H33I0.5744330.4845670.4768200.057*0.154 (3)
H33J0.5602750.4402850.5451160.057*0.154 (3)
C34E0.626 (3)0.540 (4)0.547 (4)0.053 (11)0.154 (3)
H34M0.6642840.5463490.5256490.079*0.154 (3)
H34N0.6328010.5244430.5916940.079*0.154 (3)
H34O0.6047680.6003890.5435070.079*0.154 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Hg10.02327 (15)0.01836 (14)0.0316 (2)0.00293 (12)0.00245 (14)0.00065 (15)
Hg20.03127 (17)0.02021 (14)0.02125 (17)0.00420 (13)0.00170 (14)0.00320 (15)
Br120.0428 (6)0.0365 (5)0.0318 (5)0.0087 (4)0.0078 (4)0.0070 (4)
Br220.0587 (7)0.0351 (5)0.0396 (6)0.0027 (5)0.0191 (5)0.0035 (4)
Br110.0125 (18)0.0248 (11)0.067 (2)0.0023 (11)0.0074 (14)0.0025 (10)
Br210.0360 (11)0.019 (3)0.029 (5)0.0054 (18)0.008 (4)0.005 (3)
Cl110.0125 (18)0.0248 (11)0.067 (2)0.0023 (11)0.0074 (14)0.0025 (10)
Cl210.0360 (11)0.019 (3)0.029 (5)0.0054 (18)0.008 (4)0.005 (3)
N1A0.028 (4)0.032 (4)0.013 (3)0.005 (3)0.005 (3)0.005 (3)
N2A0.041 (4)0.031 (4)0.026 (4)0.010 (3)0.002 (3)0.000 (3)
N3A0.030 (4)0.012 (3)0.022 (4)0.005 (3)0.004 (3)0.001 (3)
N4A0.050 (5)0.019 (4)0.034 (5)0.015 (3)0.012 (4)0.007 (3)
C1A0.030 (4)0.020 (4)0.015 (4)0.000 (3)0.002 (3)0.004 (3)
C2A0.031 (7)0.042 (7)0.022 (6)0.004 (6)0.000 (6)0.006 (6)
C3A0.036 (8)0.049 (8)0.024 (7)0.007 (7)0.002 (7)0.007 (7)
C4A0.041 (8)0.055 (8)0.030 (7)0.010 (8)0.009 (7)0.010 (7)
C5A0.044 (8)0.059 (8)0.026 (7)0.003 (8)0.007 (7)0.006 (7)
C6A0.041 (8)0.055 (8)0.023 (7)0.003 (7)0.005 (7)0.002 (7)
C7A0.037 (7)0.045 (7)0.023 (6)0.004 (6)0.002 (6)0.004 (6)
C2C0.032 (5)0.043 (6)0.022 (5)0.004 (4)0.001 (4)0.006 (4)
C3C0.036 (7)0.047 (7)0.025 (5)0.006 (5)0.005 (5)0.008 (5)
C4C0.042 (7)0.059 (7)0.029 (5)0.008 (7)0.016 (5)0.009 (6)
C5C0.044 (7)0.066 (7)0.022 (5)0.008 (6)0.011 (5)0.006 (5)
C6C0.039 (7)0.060 (7)0.022 (5)0.008 (6)0.006 (5)0.004 (5)
C7C0.035 (6)0.047 (6)0.025 (5)0.006 (5)0.005 (4)0.004 (5)
C8A0.058 (7)0.049 (6)0.023 (5)0.019 (5)0.002 (5)0.008 (4)
C9A0.037 (6)0.097 (10)0.039 (6)0.025 (6)0.012 (5)0.022 (6)
C10A0.085 (10)0.123 (15)0.059 (9)0.067 (11)0.002 (8)0.023 (9)
C11A0.081 (11)0.17 (2)0.058 (10)0.067 (12)0.007 (8)0.062 (12)
C12A0.063 (9)0.21 (2)0.033 (8)0.037 (12)0.009 (7)0.049 (11)
C13A0.040 (5)0.017 (4)0.020 (4)0.004 (4)0.001 (4)0.002 (3)
C14A0.031 (4)0.017 (3)0.027 (5)0.007 (3)0.002 (4)0.000 (4)
C15A0.042 (5)0.017 (4)0.026 (5)0.003 (4)0.006 (4)0.000 (3)
C16A0.038 (5)0.017 (4)0.022 (5)0.002 (4)0.002 (4)0.002 (3)
C17A0.037 (5)0.013 (4)0.017 (4)0.004 (3)0.002 (3)0.002 (3)
C18A0.039 (5)0.015 (4)0.011 (4)0.002 (3)0.002 (3)0.003 (3)
C19A0.039 (5)0.040 (5)0.027 (5)0.010 (4)0.015 (4)0.008 (4)
C20A0.042 (10)0.081 (13)0.045 (10)0.012 (10)0.024 (8)0.021 (10)
C21A0.040 (9)0.028 (9)0.069 (12)0.002 (7)0.017 (9)0.011 (8)
C22A0.082 (13)0.075 (13)0.032 (9)0.006 (11)0.031 (9)0.001 (9)
C20C0.067 (14)0.058 (14)0.045 (13)0.009 (12)0.020 (12)0.002 (12)
C21C0.060 (13)0.063 (14)0.060 (13)0.014 (12)0.038 (11)0.020 (12)
C22C0.037 (9)0.058 (10)0.030 (9)0.010 (8)0.022 (8)0.004 (8)
C23A0.037 (5)0.021 (4)0.019 (4)0.010 (4)0.006 (4)0.006 (3)
C24A0.039 (5)0.029 (5)0.012 (4)0.012 (4)0.004 (4)0.001 (3)
C25A0.035 (5)0.045 (6)0.016 (4)0.001 (4)0.003 (4)0.006 (4)
C26A0.032 (5)0.054 (6)0.023 (5)0.002 (5)0.003 (4)0.015 (4)
C27A0.046 (6)0.059 (7)0.017 (5)0.022 (5)0.003 (4)0.007 (4)
C28A0.047 (6)0.037 (6)0.036 (6)0.022 (5)0.014 (5)0.003 (5)
C29A0.051 (6)0.029 (5)0.025 (5)0.007 (5)0.012 (4)0.013 (4)
C30A0.066 (5)0.024 (4)0.051 (4)0.007 (4)0.018 (4)0.001 (3)
C31A0.068 (5)0.028 (4)0.047 (4)0.007 (4)0.017 (4)0.006 (4)
C32A0.067 (5)0.037 (4)0.045 (5)0.001 (4)0.016 (4)0.008 (4)
C33A0.069 (7)0.047 (7)0.046 (6)0.002 (6)0.009 (6)0.006 (6)
C34A0.068 (10)0.079 (11)0.059 (10)0.007 (9)0.007 (9)0.018 (9)
C30C0.066 (5)0.024 (4)0.051 (4)0.007 (4)0.018 (4)0.001 (3)
C31C0.068 (5)0.028 (4)0.047 (4)0.007 (4)0.017 (4)0.006 (4)
C32C0.067 (5)0.037 (4)0.045 (5)0.001 (4)0.016 (4)0.008 (4)
C33C0.066 (8)0.044 (8)0.044 (7)0.002 (8)0.014 (7)0.008 (7)
C34C0.061 (14)0.058 (14)0.042 (14)0.002 (14)0.014 (13)0.014 (13)
C30F0.066 (5)0.024 (4)0.051 (4)0.007 (4)0.018 (4)0.001 (3)
C31F0.068 (7)0.031 (6)0.051 (6)0.003 (6)0.017 (6)0.002 (6)
C32F0.068 (7)0.037 (6)0.047 (6)0.003 (6)0.014 (6)0.007 (6)
C33F0.071 (10)0.035 (9)0.047 (9)0.006 (9)0.013 (9)0.005 (9)
C34F0.08 (3)0.05 (3)0.04 (2)0.00 (3)0.00 (2)0.01 (2)
N1B0.026 (4)0.012 (3)0.029 (4)0.009 (3)0.007 (3)0.001 (3)
N2B0.034 (4)0.020 (3)0.013 (3)0.002 (3)0.007 (3)0.001 (3)
N3B0.023 (3)0.024 (3)0.010 (3)0.007 (3)0.003 (3)0.002 (3)
N4B0.031 (4)0.028 (4)0.021 (4)0.006 (3)0.004 (3)0.002 (3)
C1B0.029 (4)0.017 (4)0.015 (4)0.002 (3)0.002 (3)0.001 (3)
C2B0.023 (4)0.017 (4)0.035 (5)0.003 (3)0.008 (4)0.006 (4)
C3B0.033 (5)0.017 (4)0.052 (6)0.002 (4)0.007 (5)0.002 (4)
C4B0.029 (5)0.036 (5)0.050 (6)0.002 (4)0.013 (5)0.001 (5)
C5B0.029 (5)0.038 (5)0.027 (5)0.014 (4)0.009 (4)0.002 (4)
C6B0.039 (5)0.030 (5)0.020 (4)0.016 (4)0.012 (4)0.006 (4)
C7B0.029 (5)0.020 (4)0.014 (4)0.003 (4)0.005 (3)0.002 (3)
C8B0.044 (6)0.017 (4)0.044 (6)0.003 (4)0.021 (4)0.003 (4)
C9B0.056 (7)0.041 (6)0.034 (6)0.009 (5)0.011 (5)0.009 (5)
C10B0.049 (6)0.039 (6)0.040 (6)0.006 (5)0.007 (5)0.001 (5)
C11B0.054 (7)0.054 (7)0.056 (7)0.008 (6)0.011 (6)0.014 (6)
C12B0.081 (9)0.027 (5)0.051 (7)0.022 (6)0.021 (6)0.023 (5)
C13B0.023 (4)0.016 (3)0.019 (4)0.000 (3)0.003 (3)0.006 (3)
C14B0.025 (4)0.014 (4)0.025 (5)0.001 (3)0.001 (3)0.001 (3)
C15B0.022 (4)0.011 (4)0.024 (4)0.001 (3)0.010 (3)0.006 (3)
C16B0.015 (3)0.014 (4)0.027 (5)0.002 (3)0.001 (3)0.007 (3)
C17B0.023 (4)0.020 (4)0.016 (4)0.001 (3)0.003 (3)0.009 (3)
C18B0.025 (4)0.011 (4)0.019 (4)0.001 (3)0.001 (3)0.002 (3)
C19B0.030 (5)0.020 (4)0.036 (5)0.001 (4)0.008 (4)0.004 (4)
C20B0.048 (6)0.029 (5)0.035 (5)0.001 (4)0.021 (5)0.001 (4)
C21B0.037 (5)0.018 (4)0.045 (6)0.001 (4)0.006 (4)0.009 (4)
C22B0.024 (5)0.023 (4)0.065 (7)0.005 (4)0.003 (4)0.005 (4)
C23B0.020 (4)0.021 (4)0.019 (4)0.002 (3)0.003 (3)0.001 (3)
C24B0.033 (5)0.028 (4)0.010 (4)0.003 (4)0.003 (3)0.002 (3)
C25B0.093 (10)0.045 (7)0.027 (6)0.039 (7)0.007 (6)0.002 (5)
C26B0.098 (11)0.068 (9)0.021 (5)0.048 (8)0.005 (6)0.002 (5)
C27B0.062 (7)0.051 (6)0.012 (4)0.008 (5)0.007 (4)0.000 (4)
C28B0.042 (5)0.043 (6)0.024 (5)0.006 (5)0.012 (4)0.004 (4)
C29B0.025 (4)0.032 (5)0.018 (4)0.003 (4)0.003 (3)0.001 (4)
C30B0.031 (7)0.046 (8)0.022 (6)0.014 (6)0.000 (6)0.002 (6)
C31B0.037 (7)0.059 (8)0.032 (6)0.008 (6)0.008 (5)0.019 (6)
C32B0.066 (8)0.049 (7)0.040 (7)0.007 (7)0.017 (6)0.014 (7)
C33B0.064 (9)0.054 (9)0.032 (7)0.004 (8)0.014 (7)0.012 (8)
C34B0.083 (13)0.085 (13)0.066 (12)0.017 (12)0.003 (11)0.013 (11)
C30D0.034 (10)0.040 (10)0.018 (9)0.011 (9)0.005 (9)0.002 (9)
C31D0.038 (9)0.047 (9)0.024 (8)0.009 (8)0.001 (8)0.006 (8)
C32D0.054 (9)0.055 (9)0.038 (8)0.007 (8)0.009 (8)0.013 (9)
C33D0.063 (10)0.055 (10)0.041 (9)0.004 (9)0.009 (9)0.014 (9)
C34D0.062 (15)0.059 (16)0.035 (14)0.011 (15)0.016 (14)0.016 (14)
C30E0.034 (10)0.042 (11)0.019 (10)0.010 (9)0.002 (9)0.001 (9)
C31E0.036 (11)0.040 (11)0.019 (11)0.006 (10)0.006 (10)0.002 (10)
C32E0.043 (12)0.040 (12)0.025 (11)0.004 (12)0.011 (11)0.006 (11)
C33E0.058 (10)0.049 (9)0.037 (9)0.004 (9)0.011 (9)0.004 (9)
C34E0.06 (2)0.05 (2)0.04 (2)0.00 (2)0.003 (19)0.008 (19)
Geometric parameters (Å, º) top
Hg1—N1A2.313 (7)C34C—H34E0.9800
Hg1—N1B2.343 (6)C34C—H34F0.9800
Hg1—Cl112.373 (19)C30F—C31F1.53 (3)
Hg1—Br122.5083 (10)C30F—H30K0.9900
Hg1—Br112.593 (4)C30F—H30L0.9900
Hg2—N3Ai2.316 (6)C31F—C32F1.52 (3)
Hg2—N3B2.327 (6)C31F—H31K0.9900
Hg2—Cl212.48 (4)C31F—H31L0.9900
Hg2—Br222.5147 (11)C32F—C33F1.53 (3)
Hg2—Br212.57 (2)C32F—H32K0.9900
N1A—C1A1.326 (11)C32F—H32L0.9900
N1A—C2A1.39 (2)C33F—C34F1.50 (3)
N1A—C2C1.408 (15)C33F—H33K0.9900
N2A—C1A1.364 (12)C33F—H33L0.9900
N2A—C7A1.38 (2)C34F—H34P0.9800
N2A—C7C1.384 (15)C34F—H34Q0.9800
N2A—C8A1.460 (13)C34F—H34R0.9800
N3A—C23A1.324 (11)N1B—C1B1.340 (11)
N3A—C24A1.391 (12)N1B—C2B1.398 (11)
N4A—C23A1.372 (12)N2B—C1B1.368 (11)
N4A—C29A1.376 (14)N2B—C7B1.388 (11)
N4A—C30F1.461 (13)N2B—C8B1.456 (11)
N4A—C30A1.461 (13)N3B—C23B1.300 (11)
N4A—C30C1.461 (13)N3B—C24B1.396 (12)
C1A—C13A1.466 (12)N4B—C23B1.354 (11)
C2A—C7A1.38 (3)N4B—C29B1.385 (12)
C2A—C3A1.39 (3)N4B—C30B1.465 (17)
C3A—C4A1.41 (3)N4B—C30E1.50 (7)
C3A—H3AA0.9500N4B—C30D1.62 (5)
C4A—C5A1.36 (3)C1B—C13B1.464 (11)
C4A—H4AA0.9500C2B—C3B1.397 (13)
C5A—C6A1.37 (3)C2B—C7B1.400 (12)
C5A—H5AA0.9500C3B—C4B1.375 (14)
C6A—C7A1.40 (3)C3B—H3BA0.9500
C6A—H6AA0.9500C4B—C5B1.407 (14)
C2C—C7C1.387 (17)C4B—H4BA0.9500
C2C—C3C1.402 (17)C5B—C6B1.375 (14)
C3C—C4C1.40 (2)C5B—H5BA0.9500
C3C—H3CA0.9500C6B—C7B1.394 (12)
C4C—C5C1.36 (2)C6B—H6BA0.9500
C4C—H4CA0.9500C8B—C9B1.513 (13)
C5C—C6C1.374 (19)C8B—H8BA0.9900
C5C—H5CA0.9500C8B—H8BB0.9900
C6C—C7C1.398 (16)C9B—C10B1.532 (14)
C6C—H6CA0.9500C9B—H9BA0.9900
C8A—C9A1.497 (17)C9B—H9BB0.9900
C8A—H8AA0.9900C10B—C11B1.528 (14)
C8A—H8AB0.9900C10B—H10C0.9900
C9A—C10A1.52 (2)C10B—H10D0.9900
C9A—H9A10.9900C11B—C12B1.510 (15)
C9A—H9A20.9900C11B—H11C0.9900
C10A—C11A1.53 (2)C11B—H11D0.9900
C10A—H10A0.9900C12B—H12D0.9800
C10A—H10B0.9900C12B—H12E0.9800
C11A—C12A1.49 (3)C12B—H12F0.9800
C11A—H11A0.9900C13B—C14B1.392 (12)
C11A—H11B0.9900C13B—C18B1.393 (12)
C12A—H12A0.9800C14B—C15B1.401 (12)
C12A—H12B0.9800C14B—H14B0.9500
C12A—H12C0.9800C15B—C16B1.380 (12)
C13A—C18A1.391 (13)C15B—C19B1.547 (11)
C13A—C14A1.406 (13)C16B—C17B1.401 (12)
C14A—C15A1.400 (13)C16B—H16B0.9500
C14A—H14A0.9500C17B—C18B1.390 (12)
C15A—C16A1.383 (14)C17B—C23B1.467 (12)
C15A—C19A1.532 (13)C18B—H18B0.9500
C16A—C17A1.383 (13)C19B—C20B1.518 (14)
C16A—H16A0.9500C19B—C22B1.526 (14)
C17A—C18A1.395 (11)C19B—C21B1.537 (12)
C17A—C23A1.466 (13)C20B—H20G0.9800
C18A—H18A0.9500C20B—H20H0.9800
C19A—C20C1.43 (4)C20B—H20I0.9800
C19A—C22A1.47 (3)C21B—H21G0.9800
C19A—C21C1.54 (3)C21B—H21H0.9800
C19A—C20A1.54 (2)C21B—H21I0.9800
C19A—C21A1.55 (2)C22B—H22G0.9800
C19A—C22C1.58 (3)C22B—H22H0.9800
C20A—H20A0.9800C22B—H22I0.9800
C20A—H20B0.9800C24B—C29B1.391 (13)
C20A—H20C0.9800C24B—C25B1.402 (14)
C21A—H21A0.9800C25B—C26B1.366 (17)
C21A—H21B0.9800C25B—H25B0.9500
C21A—H21C0.9800C26B—C27B1.398 (16)
C22A—H22A0.9800C26B—H26B0.9500
C22A—H22B0.9800C27B—C28B1.365 (16)
C22A—H22C0.9800C27B—H27B0.9500
C20C—H20D0.9800C28B—C29B1.395 (13)
C20C—H20E0.9800C28B—H28B0.9500
C20C—H20F0.9800C30B—C31B1.534 (19)
C21C—H21D0.9800C30B—H30C0.9900
C21C—H21E0.9800C30B—H30D0.9900
C21C—H21F0.9800C31B—C32B1.500 (19)
C22C—H22D0.9800C31B—H31C0.9900
C22C—H22E0.9800C31B—H31D0.9900
C22C—H22F0.9800C32B—C33B1.52 (2)
C24A—C29A1.390 (13)C32B—H32C0.9900
C24A—C25A1.406 (14)C32B—H32D0.9900
C25A—C26A1.378 (14)C33B—C34B1.48 (2)
C25A—H25A0.9500C33B—H33C0.9900
C26A—C27A1.385 (16)C33B—H33D0.9900
C26A—H26A0.9500C34B—H34G0.9800
C27A—C28A1.358 (17)C34B—H34H0.9800
C27A—H27A0.9500C34B—H34I0.9800
C28A—C29A1.415 (14)C30D—C31D1.52 (2)
C28A—H28A0.9500C30D—H30G0.9900
C30A—C31A1.559 (15)C30D—H30H0.9900
C30A—H30A0.9900C31D—C32D1.50 (2)
C30A—H30B0.9900C31D—H31G0.9900
C31A—C32A1.519 (17)C31D—H31H0.9900
C31A—H31A0.9900C32D—C33D1.53 (3)
C31A—H31B0.9900C32D—H32G0.9900
C32A—C33A1.544 (18)C32D—H32H0.9900
C32A—H32A0.9900C33D—C34D1.49 (3)
C32A—H32B0.9900C33D—H33G0.9900
C33A—C34A1.51 (2)C33D—H33H0.9900
C33A—H33A0.9900C34D—H34J0.9800
C33A—H33B0.9900C34D—H34K0.9800
C34A—H34A0.9800C34D—H34L0.9800
C34A—H34B0.9800C30E—C31E1.53 (3)
C34A—H34C0.9800C30E—H30I0.9900
C30C—C31C1.559 (15)C30E—H30J0.9900
C30C—H30E0.9900C31E—C32E1.52 (3)
C30C—H30F0.9900C31E—H31I0.9900
C31C—C32C1.519 (17)C31E—H31J0.9900
C31C—H31E0.9900C32E—C33E1.53 (3)
C31C—H31F0.9900C32E—H32I0.9900
C32C—C33C1.53 (3)C32E—H32J0.9900
C32C—H32E0.9900C33E—C34E1.50 (3)
C32C—H32F0.9900C33E—H33I0.9900
C33C—C34C1.50 (3)C33E—H33J0.9900
C33C—H33E0.9900C34E—H34M0.9800
C33C—H33F0.9900C34E—H34N0.9800
C34C—H34D0.9800C34E—H34O0.9800
N1A—Hg1—N1B99.4 (3)H34D—C34C—H34F109.5
N1A—Hg1—Cl11107.1 (6)H34E—C34C—H34F109.5
N1B—Hg1—Cl11108.0 (5)N4A—C30F—C31F110 (3)
N1A—Hg1—Br12115.82 (18)N4A—C30F—H30K109.6
N1B—Hg1—Br12111.26 (17)C31F—C30F—H30K109.6
Cl11—Hg1—Br12114.1 (5)N4A—C30F—H30L109.6
N1A—Hg1—Br11103.9 (2)C31F—C30F—H30L109.6
N1B—Hg1—Br11105.2 (2)H30K—C30F—H30L108.2
Br12—Hg1—Br11119.01 (12)C32F—C31F—C30F112 (3)
N3Ai—Hg2—N3B97.2 (2)C32F—C31F—H31K109.3
N3Ai—Hg2—Cl21101.7 (8)C30F—C31F—H31K109.3
N3B—Hg2—Cl21105.0 (9)C32F—C31F—H31L109.3
N3Ai—Hg2—Br22115.13 (18)C30F—C31F—H31L109.3
N3B—Hg2—Br22109.95 (17)H31K—C31F—H31L108.0
Cl21—Hg2—Br22124.1 (7)C31F—C32F—C33F110 (3)
N3Ai—Hg2—Br21105.3 (5)C31F—C32F—H32K109.6
N3B—Hg2—Br21107.8 (5)C33F—C32F—H32K109.6
Br22—Hg2—Br21119.1 (4)C31F—C32F—H32L109.6
C1A—N1A—C2A106 (2)C33F—C32F—H32L109.6
C1A—N1A—C2C105.2 (10)H32K—C32F—H32L108.1
C1A—N1A—Hg1124.8 (6)C34F—C33F—C32F110 (3)
C2A—N1A—Hg1129 (2)C34F—C33F—H33K109.6
C2C—N1A—Hg1129.4 (9)C32F—C33F—H33K109.6
C1A—N2A—C7A106 (2)C34F—C33F—H33L109.6
C1A—N2A—C7C108.1 (11)C32F—C33F—H33L109.6
C1A—N2A—C8A127.7 (8)H33K—C33F—H33L108.2
C7A—N2A—C8A126 (2)C33F—C34F—H34P109.5
C7C—N2A—C8A123.0 (11)C33F—C34F—H34Q109.5
C23A—N3A—C24A106.5 (7)H34P—C34F—H34Q109.5
C23A—N3A—Hg2ii125.9 (6)C33F—C34F—H34R109.5
C24A—N3A—Hg2ii125.5 (6)H34P—C34F—H34R109.5
C23A—N4A—C29A107.0 (8)H34Q—C34F—H34R109.5
C23A—N4A—C30F127.6 (9)C1B—N1B—C2B106.2 (7)
C29A—N4A—C30F125.0 (8)C1B—N1B—Hg1124.8 (5)
C23A—N4A—C30A127.6 (9)C2B—N1B—Hg1124.7 (5)
C29A—N4A—C30A125.0 (8)C1B—N2B—C7B107.4 (7)
C23A—N4A—C30C127.6 (9)C1B—N2B—C8B128.6 (8)
C29A—N4A—C30C125.0 (8)C7B—N2B—C8B123.9 (7)
N1A—C1A—N2A111.6 (7)C23B—N3B—C24B106.1 (7)
N1A—C1A—C13A124.8 (8)C23B—N3B—Hg2123.6 (5)
N2A—C1A—C13A123.5 (8)C24B—N3B—Hg2129.7 (5)
C7A—C2A—N1A108 (3)C23B—N4B—C29B108.0 (7)
C7A—C2A—C3A123 (2)C23B—N4B—C30B132.5 (9)
N1A—C2A—C3A129 (4)C29B—N4B—C30B118.8 (9)
C2A—C3A—C4A116 (3)C23B—N4B—C30E117 (3)
C2A—C3A—H3AA122.1C29B—N4B—C30E133 (3)
C4A—C3A—H3AA122.1C23B—N4B—C30D122.4 (17)
C5A—C4A—C3A120 (3)C29B—N4B—C30D123.3 (19)
C5A—C4A—H4AA120.0N1B—C1B—N2B111.4 (7)
C3A—C4A—H4AA120.0N1B—C1B—C13B123.1 (7)
C4A—C5A—C6A125 (3)N2B—C1B—C13B125.5 (7)
C4A—C5A—H5AA117.3C3B—C2B—N1B130.5 (8)
C6A—C5A—H5AA117.3C3B—C2B—C7B120.8 (8)
C5A—C6A—C7A115 (3)N1B—C2B—C7B108.8 (7)
C5A—C6A—H6AA122.5C4B—C3B—C2B117.1 (9)
C7A—C6A—H6AA122.5C4B—C3B—H3BA121.4
N2A—C7A—C2A107 (3)C2B—C3B—H3BA121.4
N2A—C7A—C6A131 (4)C3B—C4B—C5B122.2 (9)
C2A—C7A—C6A121 (2)C3B—C4B—H4BA118.9
C7C—C2C—C3C118.4 (12)C5B—C4B—H4BA118.9
C7C—C2C—N1A109.6 (14)C6B—C5B—C4B120.7 (9)
C3C—C2C—N1A132.0 (15)C6B—C5B—H5BA119.7
C4C—C3C—C2C118.4 (13)C4B—C5B—H5BA119.7
C4C—C3C—H3CA120.8C5B—C6B—C7B117.7 (8)
C2C—C3C—H3CA120.8C5B—C6B—H6BA121.1
C5C—C4C—C3C121.4 (13)C7B—C6B—H6BA121.1
C5C—C4C—H4CA119.3N2B—C7B—C6B132.3 (8)
C3C—C4C—H4CA119.3N2B—C7B—C2B106.2 (7)
C4C—C5C—C6C121.7 (13)C6B—C7B—C2B121.4 (8)
C4C—C5C—H5CA119.2N2B—C8B—C9B113.6 (8)
C6C—C5C—H5CA119.2N2B—C8B—H8BA108.8
C5C—C6C—C7C117.1 (13)C9B—C8B—H8BA108.8
C5C—C6C—H6CA121.5N2B—C8B—H8BB108.8
C7C—C6C—H6CA121.5C9B—C8B—H8BB108.8
N2A—C7C—C2C105.3 (14)H8BA—C8B—H8BB107.7
N2A—C7C—C6C131.7 (16)C8B—C9B—C10B110.7 (9)
C2C—C7C—C6C122.9 (12)C8B—C9B—H9BA109.5
N2A—C8A—C9A113.0 (11)C10B—C9B—H9BA109.5
N2A—C8A—H8AA109.0C8B—C9B—H9BB109.5
C9A—C8A—H8AA109.0C10B—C9B—H9BB109.5
N2A—C8A—H8AB109.0H9BA—C9B—H9BB108.1
C9A—C8A—H8AB109.0C11B—C10B—C9B113.6 (9)
H8AA—C8A—H8AB107.8C11B—C10B—H10C108.8
C8A—C9A—C10A111.0 (14)C9B—C10B—H10C108.8
C8A—C9A—H9A1109.4C11B—C10B—H10D108.8
C10A—C9A—H9A1109.4C9B—C10B—H10D108.8
C8A—C9A—H9A2109.4H10C—C10B—H10D107.7
C10A—C9A—H9A2109.4C12B—C11B—C10B112.0 (10)
H9A1—C9A—H9A2108.0C12B—C11B—H11C109.2
C9A—C10A—C11A114.3 (12)C10B—C11B—H11C109.2
C9A—C10A—H10A108.7C12B—C11B—H11D109.2
C11A—C10A—H10A108.7C10B—C11B—H11D109.2
C9A—C10A—H10B108.7H11C—C11B—H11D107.9
C11A—C10A—H10B108.7C11B—C12B—H12D109.5
H10A—C10A—H10B107.6C11B—C12B—H12E109.5
C12A—C11A—C10A115.5 (18)H12D—C12B—H12E109.5
C12A—C11A—H11A108.4C11B—C12B—H12F109.5
C10A—C11A—H11A108.4H12D—C12B—H12F109.5
C12A—C11A—H11B108.4H12E—C12B—H12F109.5
C10A—C11A—H11B108.4C14B—C13B—C18B120.3 (8)
H11A—C11A—H11B107.5C14B—C13B—C1B117.6 (7)
C11A—C12A—H12A109.5C18B—C13B—C1B122.1 (7)
C11A—C12A—H12B109.5C13B—C14B—C15B120.8 (8)
H12A—C12A—H12B109.5C13B—C14B—H14B119.6
C11A—C12A—H12C109.5C15B—C14B—H14B119.6
H12A—C12A—H12C109.5C16B—C15B—C14B118.1 (7)
H12B—C12A—H12C109.5C16B—C15B—C19B121.9 (7)
C18A—C13A—C14A119.6 (8)C14B—C15B—C19B119.9 (8)
C18A—C13A—C1A121.0 (8)C15B—C16B—C17B121.8 (7)
C14A—C13A—C1A119.4 (8)C15B—C16B—H16B119.1
C15A—C14A—C13A121.0 (8)C17B—C16B—H16B119.1
C15A—C14A—H14A119.5C18B—C17B—C16B119.4 (8)
C13A—C14A—H14A119.5C18B—C17B—C23B121.6 (8)
C16A—C15A—C14A117.6 (8)C16B—C17B—C23B118.8 (7)
C16A—C15A—C19A120.3 (8)C17B—C18B—C13B119.5 (8)
C14A—C15A—C19A122.0 (9)C17B—C18B—H18B120.2
C17A—C16A—C15A122.5 (9)C13B—C18B—H18B120.2
C17A—C16A—H16A118.8C20B—C19B—C22B109.3 (8)
C15A—C16A—H16A118.8C20B—C19B—C21B109.5 (8)
C16A—C17A—C18A119.6 (9)C22B—C19B—C21B108.4 (8)
C16A—C17A—C23A118.6 (8)C20B—C19B—C15B108.7 (7)
C18A—C17A—C23A121.8 (8)C22B—C19B—C15B110.9 (8)
C13A—C18A—C17A119.6 (8)C21B—C19B—C15B110.0 (7)
C13A—C18A—H18A120.2C19B—C20B—H20G109.5
C17A—C18A—H18A120.2C19B—C20B—H20H109.5
C20C—C19A—C15A111.3 (15)H20G—C20B—H20H109.5
C22A—C19A—C15A110.8 (12)C19B—C20B—H20I109.5
C20C—C19A—C21C117 (2)H20G—C20B—H20I109.5
C15A—C19A—C21C109.6 (13)H20H—C20B—H20I109.5
C22A—C19A—C20A108.3 (16)C19B—C21B—H21G109.5
C15A—C19A—C20A114.6 (11)C19B—C21B—H21H109.5
C22A—C19A—C21A107.8 (16)H21G—C21B—H21H109.5
C15A—C19A—C21A109.7 (10)C19B—C21B—H21I109.5
C20A—C19A—C21A105.4 (15)H21G—C21B—H21I109.5
C20C—C19A—C22C109.7 (19)H21H—C21B—H21I109.5
C15A—C19A—C22C105.0 (12)C19B—C22B—H22G109.5
C21C—C19A—C22C103.8 (18)C19B—C22B—H22H109.5
C19A—C20A—H20A109.5H22G—C22B—H22H109.5
C19A—C20A—H20B109.5C19B—C22B—H22I109.5
H20A—C20A—H20B109.5H22G—C22B—H22I109.5
C19A—C20A—H20C109.5H22H—C22B—H22I109.5
H20A—C20A—H20C109.5N3B—C23B—N4B112.1 (7)
H20B—C20A—H20C109.5N3B—C23B—C17B124.0 (7)
C19A—C21A—H21A109.5N4B—C23B—C17B124.0 (7)
C19A—C21A—H21B109.5C29B—C24B—N3B109.2 (8)
H21A—C21A—H21B109.5C29B—C24B—C25B119.3 (9)
C19A—C21A—H21C109.5N3B—C24B—C25B131.5 (9)
H21A—C21A—H21C109.5C26B—C25B—C24B117.8 (11)
H21B—C21A—H21C109.5C26B—C25B—H25B121.1
C19A—C22A—H22A109.5C24B—C25B—H25B121.1
C19A—C22A—H22B109.5C25B—C26B—C27B122.7 (11)
H22A—C22A—H22B109.5C25B—C26B—H26B118.6
C19A—C22A—H22C109.5C27B—C26B—H26B118.6
H22A—C22A—H22C109.5C28B—C27B—C26B119.9 (10)
H22B—C22A—H22C109.5C28B—C27B—H27B120.1
C19A—C20C—H20D109.5C26B—C27B—H27B120.1
C19A—C20C—H20E109.5C27B—C28B—C29B118.2 (9)
H20D—C20C—H20E109.5C27B—C28B—H28B120.9
C19A—C20C—H20F109.5C29B—C28B—H28B120.9
H20D—C20C—H20F109.5N4B—C29B—C24B104.6 (8)
H20E—C20C—H20F109.5N4B—C29B—C28B133.3 (9)
C19A—C21C—H21D109.5C24B—C29B—C28B122.0 (9)
C19A—C21C—H21E109.5N4B—C30B—C31B113.0 (14)
H21D—C21C—H21E109.5N4B—C30B—H30C109.0
C19A—C21C—H21F109.5C31B—C30B—H30C109.0
H21D—C21C—H21F109.5N4B—C30B—H30D109.0
H21E—C21C—H21F109.5C31B—C30B—H30D109.0
C19A—C22C—H22D109.5H30C—C30B—H30D107.8
C19A—C22C—H22E109.5C32B—C31B—C30B122.3 (15)
H22D—C22C—H22E109.5C32B—C31B—H31C106.8
C19A—C22C—H22F109.5C30B—C31B—H31C106.8
H22D—C22C—H22F109.5C32B—C31B—H31D106.8
H22E—C22C—H22F109.5C30B—C31B—H31D106.8
N3A—C23A—N4A111.3 (8)H31C—C31B—H31D106.6
N3A—C23A—C17A123.7 (8)C31B—C32B—C33B114.0 (15)
N4A—C23A—C17A124.9 (8)C31B—C32B—H32C108.8
C29A—C24A—N3A108.5 (9)C33B—C32B—H32C108.8
C29A—C24A—C25A120.0 (9)C31B—C32B—H32D108.8
N3A—C24A—C25A131.4 (8)C33B—C32B—H32D108.8
C26A—C25A—C24A116.9 (10)H32C—C32B—H32D107.7
C26A—C25A—H25A121.5C34B—C33B—C32B109.8 (18)
C24A—C25A—H25A121.5C34B—C33B—H33C109.7
C25A—C26A—C27A121.8 (10)C32B—C33B—H33C109.7
C25A—C26A—H26A119.1C34B—C33B—H33D109.7
C27A—C26A—H26A119.1C32B—C33B—H33D109.7
C28A—C27A—C26A123.3 (10)H33C—C33B—H33D108.2
C28A—C27A—H27A118.4C33B—C34B—H34G109.5
C26A—C27A—H27A118.4C33B—C34B—H34H109.5
C27A—C28A—C29A115.3 (9)H34G—C34B—H34H109.5
C27A—C28A—H28A122.4C33B—C34B—H34I109.5
C29A—C28A—H28A122.4H34G—C34B—H34I109.5
N4A—C29A—C24A106.6 (9)H34H—C34B—H34I109.5
N4A—C29A—C28A130.7 (9)C31D—C30D—N4B114 (4)
C24A—C29A—C28A122.7 (10)C31D—C30D—H30G108.8
N4A—C30A—C31A112.8 (9)N4B—C30D—H30G108.8
N4A—C30A—H30A109.0C31D—C30D—H30H108.8
C31A—C30A—H30A109.0N4B—C30D—H30H108.8
N4A—C30A—H30B109.0H30G—C30D—H30H107.7
C31A—C30A—H30B109.0C32D—C31D—C30D124 (3)
H30A—C30A—H30B107.8C32D—C31D—H31G106.4
C32A—C31A—C30A115.4 (10)C30D—C31D—H31G106.4
C32A—C31A—H31A108.4C32D—C31D—H31H106.4
C30A—C31A—H31A108.4C30D—C31D—H31H106.4
C32A—C31A—H31B108.4H31G—C31D—H31H106.5
C30A—C31A—H31B108.4C31D—C32D—C33D117 (3)
H31A—C31A—H31B107.5C31D—C32D—H32G108.0
C31A—C32A—C33A111.6 (11)C33D—C32D—H32G108.0
C31A—C32A—H32A109.3C31D—C32D—H32H108.0
C33A—C32A—H32A109.3C33D—C32D—H32H108.0
C31A—C32A—H32B109.3H32G—C32D—H32H107.2
C33A—C32A—H32B109.3C34D—C33D—C32D112 (3)
H32A—C32A—H32B108.0C34D—C33D—H33G109.2
C34A—C33A—C32A109.9 (14)C32D—C33D—H33G109.2
C34A—C33A—H33A109.7C34D—C33D—H33H109.2
C32A—C33A—H33A109.7C32D—C33D—H33H109.2
C34A—C33A—H33B109.7H33G—C33D—H33H107.9
C32A—C33A—H33B109.7C33D—C34D—H34J109.5
H33A—C33A—H33B108.2C33D—C34D—H34K109.5
C33A—C34A—H34A109.5H34J—C34D—H34K109.5
C33A—C34A—H34B109.5C33D—C34D—H34L109.5
H34A—C34A—H34B109.5H34J—C34D—H34L109.5
C33A—C34A—H34C109.5H34K—C34D—H34L109.5
H34A—C34A—H34C109.5N4B—C30E—C31E111 (5)
H34B—C34A—H34C109.5N4B—C30E—H30I109.4
N4A—C30C—C31C112.8 (9)C31E—C30E—H30I109.4
N4A—C30C—H30E109.0N4B—C30E—H30J109.4
C31C—C30C—H30E109.0C31E—C30E—H30J109.4
N4A—C30C—H30F109.0H30I—C30E—H30J108.0
C31C—C30C—H30F109.0C32E—C31E—C30E114 (3)
H30E—C30C—H30F107.8C32E—C31E—H31I108.7
C32C—C31C—C30C115.4 (10)C30E—C31E—H31I108.7
C32C—C31C—H31E108.4C32E—C31E—H31J108.7
C30C—C31C—H31E108.4C30E—C31E—H31J108.7
C32C—C31C—H31F108.4H31I—C31E—H31J107.6
C30C—C31C—H31F108.4C31E—C32E—C33E115 (3)
H31E—C31C—H31F107.5C31E—C32E—H32I108.6
C31C—C32C—C33C128 (3)C33E—C32E—H32I108.6
C31C—C32C—H32E105.4C31E—C32E—H32J108.6
C33C—C32C—H32E105.4C33E—C32E—H32J108.6
C31C—C32C—H32F105.4H32I—C32E—H32J107.6
C33C—C32C—H32F105.4C34E—C33E—C32E111 (3)
H32E—C32C—H32F106.0C34E—C33E—H33I109.5
C34C—C33C—C32C109 (3)C32E—C33E—H33I109.5
C34C—C33C—H33E109.9C34E—C33E—H33J109.5
C32C—C33C—H33E109.9C32E—C33E—H33J109.5
C34C—C33C—H33F109.9H33I—C33E—H33J108.0
C32C—C33C—H33F109.9C33E—C34E—H34M109.5
H33E—C33C—H33F108.3C33E—C34E—H34N109.5
C33C—C34C—H34D109.5H34M—C34E—H34N109.5
C33C—C34C—H34E109.5C33E—C34E—H34O109.5
H34D—C34C—H34E109.5H34M—C34E—H34O109.5
C33C—C34C—H34F109.5H34N—C34E—H34O109.5
C2A—N1A—C1A—N2A5.7 (12)C23A—N4A—C30A—C31A102.0 (12)
C2C—N1A—C1A—N2A4.0 (10)C29A—N4A—C30A—C31A70.7 (14)
Hg1—N1A—C1A—N2A176.1 (6)N4A—C30A—C31A—C32A61.3 (16)
C2A—N1A—C1A—C13A172.5 (11)C30A—C31A—C32A—C33A172.0 (14)
C2C—N1A—C1A—C13A177.8 (9)C31A—C32A—C33A—C34A173.1 (16)
Hg1—N1A—C1A—C13A5.8 (12)C23A—N4A—C30C—C31C102.0 (12)
C7A—N2A—C1A—N1A6 (2)C29A—N4A—C30C—C31C70.7 (14)
C7C—N2A—C1A—N1A3.1 (13)N4A—C30C—C31C—C32C61.3 (16)
C8A—N2A—C1A—N1A170.6 (9)C30C—C31C—C32C—C33C176 (3)
C7A—N2A—C1A—C13A173 (2)C31C—C32C—C33C—C34C61 (8)
C7C—N2A—C1A—C13A178.7 (11)C23A—N4A—C30F—C31F71 (2)
C8A—N2A—C1A—C13A11.2 (15)C29A—N4A—C30F—C31F102 (2)
C1A—N1A—C2A—C7A3 (2)N4A—C30F—C31F—C32F48 (5)
Hg1—N1A—C2A—C7A178 (2)C30F—C31F—C32F—C33F68 (7)
C1A—N1A—C2A—C3A176 (2)C31F—C32F—C33F—C34F172 (6)
Hg1—N1A—C2A—C3A2 (2)C2B—N1B—C1B—N2B0.0 (10)
C7A—C2A—C3A—C4A0 (4)Hg1—N1B—C1B—N2B157.5 (6)
N1A—C2A—C3A—C4A180 (2)C2B—N1B—C1B—C13B179.8 (8)
C2A—C3A—C4A—C5A1 (5)Hg1—N1B—C1B—C13B22.7 (12)
C3A—C4A—C5A—C6A2 (6)C7B—N2B—C1B—N1B0.5 (10)
C4A—C5A—C6A—C7A2 (6)C8B—N2B—C1B—N1B177.0 (9)
C1A—N2A—C7A—C2A3 (3)C7B—N2B—C1B—C13B179.7 (8)
C8A—N2A—C7A—C2A173.2 (15)C8B—N2B—C1B—C13B2.8 (14)
C1A—N2A—C7A—C6A177 (4)C1B—N1B—C2B—C3B179.9 (11)
C8A—N2A—C7A—C6A7 (6)Hg1—N1B—C2B—C3B22.6 (15)
N1A—C2A—C7A—N2A0 (3)C1B—N1B—C2B—C7B0.6 (10)
C3A—C2A—C7A—N2A180 (2)Hg1—N1B—C2B—C7B157.0 (6)
N1A—C2A—C7A—C6A180 (3)N1B—C2B—C3B—C4B178.0 (10)
C3A—C2A—C7A—C6A0 (5)C7B—C2B—C3B—C4B1.6 (16)
C5A—C6A—C7A—N2A179 (4)C2B—C3B—C4B—C5B0.9 (17)
C5A—C6A—C7A—C2A1 (5)C3B—C4B—C5B—C6B0.5 (17)
C1A—N1A—C2C—C7C3.5 (11)C4B—C5B—C6B—C7B0.9 (15)
Hg1—N1A—C2C—C7C175.1 (9)C1B—N2B—C7B—C6B177.4 (9)
C1A—N1A—C2C—C3C174.8 (12)C8B—N2B—C7B—C6B4.9 (15)
Hg1—N1A—C2C—C3C3.3 (14)C1B—N2B—C7B—C2B0.8 (10)
C7C—C2C—C3C—C4C1 (2)C8B—N2B—C7B—C2B176.8 (8)
N1A—C2C—C3C—C4C179.3 (12)C5B—C6B—C7B—N2B179.6 (9)
C2C—C3C—C4C—C5C0 (3)C5B—C6B—C7B—C2B1.6 (14)
C3C—C4C—C5C—C6C3 (3)C3B—C2B—C7B—N2B179.5 (9)
C4C—C5C—C6C—C7C4 (3)N1B—C2B—C7B—N2B0.9 (10)
C1A—N2A—C7C—C2C0.7 (15)C3B—C2B—C7B—C6B2.0 (15)
C8A—N2A—C7C—C2C169.0 (10)N1B—C2B—C7B—C6B177.6 (8)
C1A—N2A—C7C—C6C175.3 (18)C1B—N2B—C8B—C9B113.5 (10)
C8A—N2A—C7C—C6C7 (3)C7B—N2B—C8B—C9B63.7 (13)
C3C—C2C—C7C—N2A176.9 (11)N2B—C8B—C9B—C10B162.5 (9)
N1A—C2C—C7C—N2A1.7 (14)C8B—C9B—C10B—C11B174.7 (10)
C3C—C2C—C7C—C6C0 (2)C9B—C10B—C11B—C12B179.5 (11)
N1A—C2C—C7C—C6C178.1 (14)N1B—C1B—C13B—C14B49.8 (12)
C5C—C6C—C7C—N2A178.3 (17)N2B—C1B—C13B—C14B129.9 (9)
C5C—C6C—C7C—C2C3 (3)N1B—C1B—C13B—C18B127.5 (9)
C1A—N2A—C8A—C9A115.5 (11)N2B—C1B—C13B—C18B52.7 (12)
C7A—N2A—C8A—C9A69 (3)C18B—C13B—C14B—C15B0.2 (12)
C7C—N2A—C8A—C9A78.6 (15)C1B—C13B—C14B—C15B177.2 (7)
N2A—C8A—C9A—C10A166.8 (10)C13B—C14B—C15B—C16B2.0 (11)
C8A—C9A—C10A—C11A76.3 (19)C13B—C14B—C15B—C19B178.9 (7)
C9A—C10A—C11A—C12A67.4 (19)C14B—C15B—C16B—C17B2.8 (11)
N1A—C1A—C13A—C18A119.2 (10)C19B—C15B—C16B—C17B179.7 (7)
N2A—C1A—C13A—C18A58.7 (12)C15B—C16B—C17B—C18B1.8 (12)
N1A—C1A—C13A—C14A62.0 (12)C15B—C16B—C17B—C23B178.3 (7)
N2A—C1A—C13A—C14A120.1 (10)C16B—C17B—C18B—C13B0.0 (11)
C18A—C13A—C14A—C15A1.2 (12)C23B—C17B—C18B—C13B176.3 (7)
C1A—C13A—C14A—C15A177.6 (8)C14B—C13B—C18B—C17B0.8 (11)
C13A—C14A—C15A—C16A1.0 (13)C1B—C13B—C18B—C17B178.1 (7)
C13A—C14A—C15A—C19A179.8 (8)C16B—C15B—C19B—C20B99.9 (10)
C14A—C15A—C16A—C17A0.6 (13)C14B—C15B—C19B—C20B77.0 (10)
C19A—C15A—C16A—C17A178.6 (8)C16B—C15B—C19B—C22B20.3 (11)
C15A—C16A—C17A—C18A2.2 (13)C14B—C15B—C19B—C22B162.9 (8)
C15A—C16A—C17A—C23A179.8 (8)C16B—C15B—C19B—C21B140.2 (8)
C14A—C13A—C18A—C17A0.3 (12)C14B—C15B—C19B—C21B43.0 (11)
C1A—C13A—C18A—C17A179.1 (7)C24B—N3B—C23B—N4B0.4 (10)
C16A—C17A—C18A—C13A2.0 (12)Hg2—N3B—C23B—N4B171.3 (5)
C23A—C17A—C18A—C13A180.0 (8)C24B—N3B—C23B—C17B179.3 (8)
C16A—C15A—C19A—C20C139.5 (19)Hg2—N3B—C23B—C17B9.0 (11)
C14A—C15A—C19A—C20C41 (2)C29B—N4B—C23B—N3B0.9 (10)
C16A—C15A—C19A—C22A61.1 (17)C30B—N4B—C23B—N3B169.3 (12)
C14A—C15A—C19A—C22A118.1 (16)C30E—N4B—C23B—N3B167 (3)
C16A—C15A—C19A—C21C9 (2)C30D—N4B—C23B—N3B154 (2)
C14A—C15A—C19A—C21C171.7 (17)C29B—N4B—C23B—C17B178.8 (8)
C16A—C15A—C19A—C20A176.0 (15)C30B—N4B—C23B—C17B11.0 (17)
C14A—C15A—C19A—C20A4.8 (18)C30E—N4B—C23B—C17B12 (3)
C16A—C15A—C19A—C21A57.8 (15)C30D—N4B—C23B—C17B26 (2)
C14A—C15A—C19A—C21A123.1 (13)C18B—C17B—C23B—N3B118.7 (9)
C16A—C15A—C19A—C22C101.9 (15)C16B—C17B—C23B—N3B57.6 (11)
C14A—C15A—C19A—C22C77.3 (15)C18B—C17B—C23B—N4B61.6 (11)
C24A—N3A—C23A—N4A0.8 (10)C16B—C17B—C23B—N4B122.0 (9)
Hg2ii—N3A—C23A—N4A163.3 (6)C23B—N3B—C24B—C29B0.3 (10)
C24A—N3A—C23A—C17A175.7 (8)Hg2—N3B—C24B—C29B171.3 (6)
Hg2ii—N3A—C23A—C17A20.2 (12)C23B—N3B—C24B—C25B178.7 (12)
C29A—N4A—C23A—N3A0.8 (11)Hg2—N3B—C24B—C25B10.3 (16)
C30F—N4A—C23A—N3A174.5 (9)C29B—C24B—C25B—C26B2.6 (19)
C30A—N4A—C23A—N3A174.5 (9)N3B—C24B—C25B—C26B179.2 (12)
C30C—N4A—C23A—N3A174.5 (9)C24B—C25B—C26B—C27B4 (2)
C29A—N4A—C23A—C17A175.6 (9)C25B—C26B—C27B—C28B3 (2)
C30F—N4A—C23A—C17A1.9 (15)C26B—C27B—C28B—C29B0.9 (18)
C30A—N4A—C23A—C17A1.9 (15)C23B—N4B—C29B—C24B1.1 (10)
C30C—N4A—C23A—C17A1.9 (15)C30B—N4B—C29B—C24B170.7 (11)
C16A—C17A—C23A—N3A57.1 (12)C30E—N4B—C29B—C24B165 (3)
C18A—C17A—C23A—N3A120.9 (9)C30D—N4B—C29B—C24B154 (2)
C16A—C17A—C23A—N4A118.9 (10)C23B—N4B—C29B—C28B178.6 (10)
C18A—C17A—C23A—N4A63.1 (12)C30B—N4B—C29B—C28B9.6 (17)
C23A—N3A—C24A—C29A0.5 (10)C30E—N4B—C29B—C28B15 (4)
Hg2ii—N3A—C24A—C29A163.7 (6)C30D—N4B—C29B—C28B26 (2)
C23A—N3A—C24A—C25A179.1 (9)N3B—C24B—C29B—N4B0.9 (10)
Hg2ii—N3A—C24A—C25A16.7 (13)C25B—C24B—C29B—N4B179.4 (10)
C29A—C24A—C25A—C26A1.2 (13)N3B—C24B—C29B—C28B178.9 (9)
N3A—C24A—C25A—C26A179.2 (9)C25B—C24B—C29B—C28B0.3 (15)
C24A—C25A—C26A—C27A0.6 (14)C27B—C28B—C29B—N4B179.8 (11)
C25A—C26A—C27A—C28A1.7 (16)C27B—C28B—C29B—C24B0.5 (16)
C26A—C27A—C28A—C29A0.8 (16)C23B—N4B—C30B—C31B102.4 (15)
C23A—N4A—C29A—C24A0.4 (11)C29B—N4B—C30B—C31B67.0 (15)
C30F—N4A—C29A—C24A174.4 (9)N4B—C30B—C31B—C32B172.4 (13)
C30A—N4A—C29A—C24A174.4 (9)C30B—C31B—C32B—C33B178.2 (16)
C30C—N4A—C29A—C24A174.4 (9)C31B—C32B—C33B—C34B177.1 (17)
C23A—N4A—C29A—C28A178.5 (11)C23B—N4B—C30D—C31D154 (2)
C30F—N4A—C29A—C28A7.6 (18)C29B—N4B—C30D—C31D57 (4)
C30A—N4A—C29A—C28A7.6 (18)N4B—C30D—C31D—C32D106 (5)
C30C—N4A—C29A—C28A7.6 (18)C30D—C31D—C32D—C33D153 (5)
N3A—C24A—C29A—N4A0.0 (11)C31D—C32D—C33D—C34D120 (5)
C25A—C24A—C29A—N4A179.6 (8)C23B—N4B—C30E—C31E94 (5)
N3A—C24A—C29A—C28A178.2 (9)C29B—N4B—C30E—C31E68 (7)
C25A—C24A—C29A—C28A2.1 (15)N4B—C30E—C31E—C32E165 (5)
C27A—C28A—C29A—N4A178.9 (10)C30E—C31E—C32E—C33E168 (6)
C27A—C28A—C29A—C24A1.1 (16)C31E—C32E—C33E—C34E179 (6)
Symmetry codes: (i) x, y1, z; (ii) x, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3A—H3AA···N1B0.952.453.29 (4)148
C8A—H8AB···Br22ii0.992.943.873 (11)158
C25A—H25A···Br21ii0.952.963.66 (2)131
C25A—H25A···Cl21ii0.952.743.45 (3)132
C28A—H28A···Br11iii0.952.963.793 (12)147
C28A—H28A···Cl11iii0.952.863.70 (2)149
C30A—H30B···Br11iii0.993.043.979 (13)158
C3B—H3BA···Br110.952.963.631 (11)129
C6B—H6BA···Br21iv0.952.883.75 (2)153
C6B—H6BA···Cl21iv0.952.893.73 (4)149
C25B—H25B···N3Ai0.952.563.332 (14)139
C30D—H30G···Br120.993.063.95 (5)150
Symmetry codes: (i) x, y1, z; (ii) x, y+1, z; (iii) x1/2, y+1, z; (iv) x+1/2, y, z.
 

Acknowledgements

RJB is grateful to NSF and the Partnership for Reduced Dimensional Materials for partial funding of this research, the Howard University Nanoscience Facility for access to liquid nitro­gen, and the NSF–MRI program for funds to purchase the X-ray diffractometer. HBS is grateful to DST, New Delhi, for a J. C. Bose National Fellowship. VR gratefully acknowledges the Council of Scientific and Industrial Research (CSIR), New Delhi, for a Senior Research Fellowship.

Funding information

Funding for this research was provided by: National Science Foundation, Directorate for Mathematical and Physical Sciences (award No. 1205608); National Science Foundation (award No. CHE0619278).

References

First citationBouchouit, M., Benzerka, S., Bouraiou, A., Merazig, H., Belfaitah, A. & Bouacida, S. (2015). Acta Cryst. E71, m253–m254.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationBruker (2002). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationCarballo, R., Castineiras, A., Conde, M. C. G. & Hiller, W. (1993). Polyhedron, 12, 1655–1660.  CSD CrossRef CAS Google Scholar
First citationCarina, R. F., Williams, A. F. & Bernardinelli, G. (1997). J. Organomet. Chem. 548, 45–48.  CSD CrossRef CAS Google Scholar
First citationChen, Y., Chen, C., Chen, H., Cao, T., Yue, Z., Liu, X. & Niu, Y. (2013). Synth. React. Inorg. Met.-Org. Nano-Met. Chem. 43, 1307–1310.  Web of Science CSD CrossRef CAS Google Scholar
First citationChen, S., Fan, R.-Q., Wang, X.-M. & Yang, Y.-L. (2014). CrystEngComm, 16, 6114–6125.  Web of Science CSD CrossRef CAS Google Scholar
First citationDey, A., Mandal, S. K. & Biradha, K. (2013). CrystEngComm, 15, 9769–9778.  Web of Science CSD CrossRef CAS Google Scholar
First citationDing, Y., Zhou, X., Jin, G., Zhao, D. & Meng, X. (2012). Synth. React. Inorg. Met.-Org. Nano-Met. Chem. 42, 438–443.  Web of Science CSD CrossRef CAS Google Scholar
First citationDu, J.-L., Wei, Z.-Z. & Hu, T.-L. (2011). Solid State Sci. 13, 1256–1260.  Web of Science CSD CrossRef CAS Google Scholar
First citationGonzalez, A. D. (2014). Organometallics, 33, 868–875.  Google Scholar
First citationHe, C.-J., Zu, E.-P. & Zhou, X.-J. (2012). Z. Kristallogr. New Cryst. Struct. 227, 445–446.  Web of Science CSD CrossRef CAS Google Scholar
First citationHu, J. Y., Liao, C. L., Hu, L. L., Zhang, C. C., Chen, S. F. & Zhao, J. (2015). Russ. J. Coord. Chem. 41, 212–219.  Web of Science CrossRef CAS Google Scholar
First citationHu, J., Liao, C., Zhao, J. & Haipeng Zhao, H. (2012). Z. Kristallogr. New Cryst. Struct. 227, 69–70.  CAS Google Scholar
First citationHuang, M., Liu, P., Chen, Y., Wang, J. & Liu, Z. (2006). J. Mol. Struct. 788, 211–217.  Web of Science CSD CrossRef CAS Google Scholar
First citationKarlsson, E. A., Lee, B., Åkermark, T., Johnston, E. V., Kärkäs, M. D., Sun, J., Hansson, Ö., Bäckvall, J. & Åkermark, B. (2011). Angew. Chem. Int. Ed. 50, 11715–11718.  CSD CrossRef CAS Google Scholar
First citationLi, J., Li, X., Lu, H., Zhu, Y., Sun, H., Guo, Y., Yue, Z., Zhao, J., Tang, M., Hou, H., Fan, Y. & Chang, J. (2012b). Inorg. Chim. Acta, 384, 163–169.  CSD CrossRef CAS Google Scholar
First citationLi, Y., Liu, Q.-K., Ma, J.-P. & Dong, Y.-B. (2012a). Acta Cryst. C68, m152–m155.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationLi, X.-P., Zhang, J.-Y., Liu, Y., Pan, M., Zheng, S.-R., Kang, B.-S. & Cheng-Yong Su, C.-Y. (2007). Inorg. Chim. Acta, 360, 2990–2996.  CSD CrossRef CAS Google Scholar
First citationLou, S.-F., Wang, Q. & Ding, J. (2012). Z. Kristallogr. New Cryst. Struct. 227, 105–106.  CAS Google Scholar
First citationManjunatha, M. N., Dikundwar, A. G. & Nagasundara, K. R. (2011). Polyhedron, 30, 1299–1304.  Web of Science CSD CrossRef CAS Google Scholar
First citationMatthews, C. J., Clegg, W., Heath, S. L., Martin, N. C., Hill, M. N. S. & Lockhart, J. C. (1998). Inorg. Chem. 37, 199–207.  Web of Science CSD CrossRef CAS Google Scholar
First citationObara, S., Itabashi, M., Okuda, F., Tamaki, S., Tanabe, Y., Ishii, Y., Nozaki, K. & Haga, M. (2006). Inorg. Chem. 45, 8907–8921.  CSD CrossRef PubMed CAS Google Scholar
First citationPalatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786–790.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationQuiroz-Castro, E., Bernes, S., Barba-Behrens, N., Tapia-Benavides, R., Contreras, R. & Noth, H. (2000). Polyhedron, 19, 1479–1484.  Web of Science CSD CrossRef CAS Google Scholar
First citationRani, V., Singh, H. B. & Butcher, R. J. (2017). Acta Cryst. E73, 341–344.  CSD CrossRef IUCr Journals Google Scholar
First citationRüttimann, S., Bernardinelli, G. & Williams, A. F. (1993). Angew. Chem. Int. Ed. 32, 392–394.  Google Scholar
First citationRüttimann, S., Piguet, C., Bernardinelli, G., Bocquet, B. & Williams, A. F. (1992). J. Am. Chem. Soc. 114, 4230–4237.  Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  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 citationShen, Y.-H., Liu, J.-G. & Xu, D.-J. (2005). Acta Cryst. E61, m1880–m1882.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSu, C.-Y., Goforth, A. M., Smith, M. D. & zur Loye, H.-C. (2003). Inorg. Chem. 42, 5685–5692.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationTam, A. Y. Y., Tsang, D. P. K., Chan, M. Y., Zhu, N. & Yam, V. W. W. (2012). Chem. Commun. 47, 3383–3385.  CSD CrossRef Google Scholar
First citationWang, Q., Fu, Z.-Y. & Yu, L.-M. (2012). Acta Cryst. E68, m44.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationWang, X.-F., Lv, Y., Su, Z., Okamura, T., Wu, G., Sun, W.-Y. & Ueyama, N. (2007). Z. Anorg. Allg. Chem. 633, 2695–2700.  Web of Science CSD CrossRef CAS Google Scholar
First citationWang, J.-J., Yan, L.-F., Li, Z.-X., Chang, Z., Hu, T.-L. & Bu, X.-H. (2009). Inorg. Chim. Acta, 362, 3147–3154.  Web of Science CSD CrossRef CAS Google Scholar
First citationWang, X., Yang, H.-Y., Zhang, C., Yuan, J. & Yang, H.-X. (2015). Z. Kristallogr. New Cryst. Struct. 230, 361–362.  CAS Google Scholar
First citationWu, J., Yang, J. & Pan, F. (2009). Acta Cryst. E65, m829.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationXiao, B., Li, W., Hou, H. & Fan, Y. (2009). J. Coord. Chem. 62, 1630–1637.  Web of Science CSD CrossRef CAS Google Scholar
First citationXiao, B., Yang, L.-J., Xiao, H.-Y. & Fang, S.-M. (2011). J. Coord. Chem. 64, 4408–4420.  Web of Science CSD CrossRef CAS Google Scholar
First citationXie, Q., Liu, S., Li, X., Wu, Q., Luo, Z., Fu, X., Cao, W., Lan, G., Li, D., Zheng, W. & Chen, T. (2014). Dalton Trans. 43, 6973–6976.  Web of Science CSD CrossRef CAS PubMed Google Scholar
First citationXu, C., Wang, X., Ding, D., Hou, H. & Fan, Y. (2011). Inorg. Chem. Commun. 14, 1410–1413.  Web of Science CSD CrossRef CAS Google Scholar
First citationYan, S., Jin, G., Yang, Y., Su, X. & Meng, X. (2012). Synth. React. Inorg. Met.-Org. Nano-Met. Chem. 42, 678–684.  CAS Google Scholar
First citationYang, G.-Y. & Luo, L.-X. (2012). Z. Kristallogr. New Cryst. Struct. 227, 441–442.  CSD CrossRef CAS Google Scholar
First citationYang, W. W., Zhong, Y. W., Yoshikawa, S., Shao, J. Y., Masaoka, S., Sakai, K., Yao, J. & Haga, M. (2012). Inorg. Chem. 51, 890–899.  Web of Science CSD CrossRef CAS PubMed Google Scholar
First citationZhang, Z., Feng, Y.-F., Wei, Q.-Y., Hu, K., Chen, Z.-L. & Liang, F.-P. (2015). CrystEngComm, 17, 6724–6735.  Web of Science CSD CrossRef CAS Google Scholar
First citationZhao, J., Li, S., Chen, S., Bai, Y. & Hu, J. (2012). J. Coord. Chem. 65, 1201–1211.  Web of Science CSD CrossRef CAS Google Scholar
First citationZhu, X.-W., Xiao, B., Yin, Z.-G., Qian, H.-Y. & Li, G.-S. (2009). Acta Cryst. E65, m912.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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