research communications
Structure of 2,2′-(5-tert-butyl-1,3-phenylene)bis(1-pentyl-1H-benzimidazol-3-ium) tetrachloridomercurate(II)
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
In the title salt, (C34H44N4)[HgCl4], the [C34H44N4]2+ cations and [HgCl4]2− anions are linked by N—H⋯Cl hydrogen bonds. One of the two n-pentyl side chains was refined as disordered over two sets of sites, with occupancies of 0.733 (18) and 0.267 (18). The geometry around the HgII atom in the [HgCl4]2− anion is distorted tetrahedral, with bond angles ranging from 98.16 (3) to 120.68 (3)°. In the [HgCl4]2− anion, there are two short Hg—Cl bonds [2.4120 (9) and 2.4171 (11) Å], one intermediate Hg—Cl bond [2.4716 (12) Å] and one long Hg—Cl bond [2.6579 (13) Å] for the Cl atom involved in a trifurcated hydrogen bond as an acceptor, including two N—H⋯Cl⋯H—N interactions as well as one C—H⋯Cl interaction. There are several C—H⋯Cl interactions, with C⋯Cl distances ranging from 3.492 (3) to 3.796 (3) Å. These link the cations and anions into a zigzag chain along the c-axis direction. In addition, there are Cl⋯Cl halogen bonds, as well as π–π interactions, with centroid-to-centroid distances of 3.4765 (18) Å, which link one of the two benzimidazole moieties into dimeric units.
Keywords: crystal structure; tetrachloridomercurate(II) salt; (benzimidazol-2-yl)benzene ligands; hydrogen bonding.
CCDC reference: 1538746
1. Chemical context
During the past few years, metallated complexes of the ligand 1,3-bis(1H-benzo[d]imidazol-2-yl)benzene 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; Obara et al., 2006; Karlsson et al., 2011; Yang et al., 2012; Tam et al., 2011; Gonzalez, 2014). As examples of the potential importance of this ligand, a highly phosphorescent iridium complex with bis(benzimidazol-2-yl)benzene ligand has been reported (Obara et al., 2006) and helical and non helical copper(I) complexes with bis(benzimidazol-2-yl)benzene have been described (Rüttimann et al., 1992). A trimeric complex has been obtained through the self assembly of cyclometalated trinuclear palladium(II) complexes (Rüttimann et al., 1993). Dinuclear zinc complexes containing a (benzimidazol-2-yl)benzene based ligand have shown anticancer activity (Xie et al., 2014).
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; Li et al., 2007; Shen et al., 2005;) or through alternative N atoms from the benzimidazole moieties (Xiao et al., 2009, 2011; Huang et al., 2006; Li et al., 2007, 2012a,b; Dey et al., 2013; Du et al., 2011; Chen et al., 2013; Su et al., 2003; Xu et al., 2011); or as discrete molecules (i.e. non-polymeric). Reports of structurally related complex have been published recently (Rani et al., 2017a,b).
An attempt was made to synthesize the compound 2,2′-(5-(tert-butyl)-2-(dichlorostibanyl)-1,3-phenylene)bis(1-pentyl-1H-benzimidazole) (2) from (4-(tert-butyl)-2,6-bis(1-pentyl-1H-benzimidazol-2-yl)phenyl)mercury(II) chloride; [C34H41N4HgCl] (1) using SbCl3 in dry 1,4-dioxane via transmetallation. Related reactions (Rani et al., 2017a,b) had yielded complexes containing an Hg atom bound to the ligand through Hg—N bonds. However, it was observed that the crystallization of compound 2 in MeOH at room temperature led to the formation of a bis-benzimidazolium cation; [C34H44N4]2+[HgCl4]2−, 3. The elaborate procedure for the synthesis of complex 1 will be published elsewhere.
2. Structural commentary
The title compound, 3, is a salt which contains [C34H44N4]2+ cations and [HgCl4]2− anions linked by N—H⋯Cl hydrogen bonds. The reaction scheme leading to this product is shown in Fig. 1. The geometry around the mercury(II) atom in the [HgCl4]2− anion is distorted tetrahedral with bond angles ranging from 98.16 (3) to 120.68 (3)°. In the [HgCl4]2− anion, there are two short Hg—Cl bonds [Hg—Cl4, 2.4120 (9) Å; Hg—Cl3, 2.4171 (11) Å], one intermediate Hg—Cl bond [Hg—Cl2, 2.4716 (12) Å] and one long Hg—Cl bond [Hg—Cl1, 2.6579 (13) Å] for the Cl atom involved in a trifurcated bond as an acceptor including two N—H⋯Cl⋯H—N interactions as well as one C—H⋯Cl interaction (see Table 1), as shown in Fig. 2. Unlike a similar structure published recently containing a closely related ligand (Rani et al., 2017a), where the Hg atom is bonded to an N atom from the benzimidazole moiety, in this instance a salt has been obtained due to the different conditions of the reaction. The structure has been published of a salt containing the tetrachloridomercurate(II) anion (Herbst et al., 2013) and a closely related ligand with n-hexyl rather than n-pentyl side chains, which was the result of an attempted transmetallate reaction between Hg and Au.
In the ligand, the dihedral angles between the benzimidazole moieties and central phenyl ring are 40.60 (9) and 38.08 (10)°, while the angle between them is 36.04 (6)°. One of the pentyl substituents was refined as disordered over two sets of sites, with occupancies of 0.733 (18)/0.267 (18). The two pentyl side chains have adopted different conformations (for the disordered side-chain only values for the major conformation will be included) and this is illustrated by their torsion angles. For C8A–C12A, the angles involved, C1—N2—C8A—C9A, N2—C8A—C9A—C10A, C8A—C9A—C10A—C11A, and C9A—C10A—C11A—C12A and are 102.1 (16), −175.0 (15), 179.7 (15), and −178.1 (9)°, respectively, while for C30–C34 they are C23—N3—C30—C31, N3—C30—C31—C32, C30—C31—C32—C33, and C31—C32—C33—C34 [−105.7 (3), 175.7 (2), 173.0 (2) and −65.8 (3)°, respectively]. Thus the first side chain is in an all-trans conformation while the second side chain has adopted a conformation where it curls up at the end.
3. Supramolecular features
In addition to the inter-ionic hydrogen bonds mentioned above, there are several C—H⋯Cl interactions with C⋯Cl distances ranging from 3.492 (3) to 3.796 (3) Å (see Table1). These link the cations and anions into a zigzag chain in the c-axis direction, as shown in Fig. 3. There are are Cl⋯Cl halogen bonds [Cl4⋯Cl42 − x, −y, 2 − z) = 3.434 (2) Å], as shown in Fig. 4. In addition, one of the two benzimidazole moieties forms dimeric units through π–π interactions (symmetry code 1 − x, −y, 2 − z) with centroid-to-centroid distances of 3.477 (2) Å.
4. Database survey
A survey of the Cambridge Structural database (CSD Version 5.37) for salts containing both the benzimidazole moiety as well as the tetrachloridomercurate(II) anion gave eight hits, including a closely related ligand with n-hexyl rather than n-pentyl side chains (Herbst et al., 2013).
5. Synthesis and crystallization
The reaction scheme is shown in Fig. 1. To a solution of 1 (0.2 g, 0.269 mmol) in dry 1,4-dioxane was added SbCl3 (0.061 g, 0.269 mmol) at room temperature. The reaction mixture was refluxed for 6 h under an inert atmosphere of N2 and filtered through Whatman filter paper. When the solvent was evaporated, a white-colored precipitate was obtained and purified by washing with hexane. The compound was dried under vacuum. Colourless block-shaped single crystals were obtained from MeOH at room temperature, yield 64% (0.120 g).
1H NMR (400 MHz, DMSO): δ 8.13 (s, 2H), 7.91 (d, J = 7.2 Hz, 2H), 7.82 (d, J = 7.2 Hz, 2H), 7.49–7.45 (m, 4H), 4.43 (m, 4H), 1.74 (m, 4H), 1.43 (s, 9H), 1.14 (m, 8H), 0.72 (m, 6H). 13C NMR (100 MHz, DMSO): 153.1, 151.4, 137.9, 134.7, 129.4, 128.5, 128.2, 124.7, 124.5, 117.8, 112.6, 45.1, 35.5, 31.3, 29.1, 28.5, 21.9, 14.1.
6. Refinement
Crystal data, data collection and structure . One of the two n-pentyl side chains was refined as disordered over two sets of sites, with occupancies of 0.733 (18) and 0.267 (18) and both conformers were constrained to have similar metrical parameters using the SAME command in SHELXL2016. H atoms were positioned geometrically and refined as riding: N—H = 0.88 Å with Uiso(H) = 1.2Ueq(N); C—H = 0.95–0.98 Å with 1.2Ueq(C) or 1.5Ueq(C) for methyl H atoms.
details are summarized in Table 2
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Supporting information
CCDC reference: 1538746
https://doi.org/10.1107/S2056989017004303/zl2697sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989017004303/zl2697Isup2.hkl
Data collection: APEX2 (Bruker, 2005); cell
APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).(C34H44N4)[HgCl4] | Z = 2 |
Mr = 851.12 | F(000) = 848 |
Triclinic, P1 | Dx = 1.591 Mg m−3 |
a = 9.806 (5) Å | Cu Kα radiation, λ = 1.54178 Å |
b = 11.264 (5) Å | Cell parameters from 9629 reflections |
c = 17.274 (5) Å | θ = 2.6–61.2° |
α = 96.727 (5)° | µ = 10.76 mm−1 |
β = 95.859 (5)° | T = 100 K |
γ = 108.575 (5)° | Block, colourless |
V = 1776.4 (13) Å3 | 0.20 × 0.11 × 0.09 mm |
Bruker Quest CCD diffractometer | 6138 reflections with I > 2σ(I) |
ω scans | Rint = 0.038 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | θmax = 66.6°, θmin = 2.6° |
Tmin = 0.497, Tmax = 0.753 | h = −11→11 |
6193 measured reflections | k = −13→13 |
6193 independent reflections | l = −20→20 |
Refinement on F2 | 67 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.020 | H-atom parameters constrained |
wR(F2) = 0.048 | w = 1/[σ2(Fo2) + (0.0123P)2 + 4.1059P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max = 0.002 |
6193 reflections | Δρmax = 1.36 e Å−3 |
410 parameters | Δρmin = −0.76 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Hg | 0.92160 (2) | 0.04332 (2) | 0.77777 (2) | 0.01320 (4) | |
Cl1 | 0.90325 (6) | 0.27221 (6) | 0.81804 (3) | 0.01173 (12) | |
Cl2 | 0.67643 (7) | −0.05962 (7) | 0.70059 (4) | 0.02181 (15) | |
Cl3 | 1.13497 (7) | 0.09387 (7) | 0.71258 (4) | 0.02149 (14) | |
Cl4 | 0.92562 (7) | −0.03357 (7) | 0.90227 (4) | 0.02064 (14) | |
N1 | 0.7288 (2) | 0.2251 (2) | 0.64598 (12) | 0.0103 (4) | |
H1A | 0.786478 | 0.240862 | 0.691195 | 0.012* | |
N2 | 0.5412 (2) | 0.2067 (2) | 0.55973 (12) | 0.0093 (4) | |
N3 | 0.4506 (2) | 0.2061 (2) | 0.96891 (12) | 0.0083 (4) | |
N4 | 0.6596 (2) | 0.2112 (2) | 0.93340 (12) | 0.0093 (4) | |
H4B | 0.731909 | 0.222420 | 0.905661 | 0.011* | |
C1 | 0.5974 (3) | 0.2376 (2) | 0.63675 (15) | 0.0093 (5) | |
C2 | 0.7605 (3) | 0.1834 (2) | 0.57342 (15) | 0.0107 (5) | |
C3 | 0.8791 (3) | 0.1515 (3) | 0.55187 (16) | 0.0145 (5) | |
H3A | 0.959906 | 0.157791 | 0.589417 | 0.017* | |
C4 | 0.8719 (3) | 0.1104 (3) | 0.47260 (17) | 0.0175 (6) | |
H4A | 0.950066 | 0.087255 | 0.455158 | 0.021* | |
C5 | 0.7527 (3) | 0.1016 (3) | 0.41676 (17) | 0.0182 (6) | |
H5A | 0.753552 | 0.074077 | 0.362738 | 0.022* | |
C6 | 0.6347 (3) | 0.1318 (3) | 0.43830 (16) | 0.0160 (6) | |
H6A | 0.553716 | 0.125044 | 0.400717 | 0.019* | |
C7 | 0.6410 (3) | 0.1728 (2) | 0.51834 (16) | 0.0112 (5) | |
C8 | 0.388 (7) | 0.196 (6) | 0.529 (4) | 0.011 (2) | 0.267 (18) |
H8A | 0.324342 | 0.184164 | 0.568393 | 0.013* | 0.267 (18) |
H8B | 0.347222 | 0.123574 | 0.487932 | 0.013* | 0.267 (18) |
C9 | 0.383 (3) | 0.295 (4) | 0.477 (3) | 0.0131 (15) | 0.267 (18) |
H9A | 0.441717 | 0.290281 | 0.434405 | 0.016* | 0.267 (18) |
H9B | 0.425475 | 0.380907 | 0.509106 | 0.016* | 0.267 (18) |
C10 | 0.226 (3) | 0.274 (2) | 0.4416 (15) | 0.0146 (14) | 0.267 (18) |
H10A | 0.185328 | 0.190262 | 0.407582 | 0.018* | 0.267 (18) |
H10B | 0.166182 | 0.274397 | 0.484450 | 0.018* | 0.267 (18) |
C11 | 0.218 (2) | 0.377 (2) | 0.3929 (14) | 0.0331 (16) | 0.267 (18) |
H11A | 0.261683 | 0.461609 | 0.426420 | 0.040* | 0.267 (18) |
H11B | 0.274690 | 0.375184 | 0.348875 | 0.040* | 0.267 (18) |
C12 | 0.061 (2) | 0.359 (2) | 0.3600 (16) | 0.045 (2) | 0.267 (18) |
H12A | 0.059390 | 0.417668 | 0.322680 | 0.067* | 0.267 (18) |
H12B | 0.008610 | 0.375105 | 0.403260 | 0.067* | 0.267 (18) |
H12C | 0.013309 | 0.271338 | 0.332829 | 0.067* | 0.267 (18) |
C8A | 0.396 (2) | 0.198 (2) | 0.5222 (15) | 0.011 (2) | 0.733 (18) |
H8AA | 0.336219 | 0.197140 | 0.562771 | 0.013* | 0.733 (18) |
H8AB | 0.355259 | 0.119230 | 0.486591 | 0.013* | 0.733 (18) |
C9A | 0.3993 (11) | 0.3134 (11) | 0.4833 (9) | 0.0131 (15) | 0.733 (18) |
H9AA | 0.457776 | 0.317383 | 0.439655 | 0.016* | 0.733 (18) |
H9AB | 0.445820 | 0.391532 | 0.522333 | 0.016* | 0.733 (18) |
C10A | 0.2453 (8) | 0.3062 (7) | 0.4513 (5) | 0.0146 (14) | 0.733 (18) |
H10C | 0.199418 | 0.227719 | 0.412483 | 0.018* | 0.733 (18) |
H10D | 0.187130 | 0.301002 | 0.495179 | 0.018* | 0.733 (18) |
C11A | 0.2417 (7) | 0.4193 (8) | 0.4123 (5) | 0.0331 (16) | 0.733 (18) |
H11C | 0.290625 | 0.498002 | 0.450600 | 0.040* | 0.733 (18) |
H11D | 0.297192 | 0.422840 | 0.367341 | 0.040* | 0.733 (18) |
C12A | 0.0887 (7) | 0.4149 (10) | 0.3828 (6) | 0.045 (2) | 0.733 (18) |
H12D | 0.093526 | 0.487533 | 0.355660 | 0.067* | 0.733 (18) |
H12E | 0.035429 | 0.418294 | 0.427505 | 0.067* | 0.733 (18) |
H12F | 0.038428 | 0.335987 | 0.346036 | 0.067* | 0.733 (18) |
C13 | 0.5319 (3) | 0.2776 (2) | 0.70281 (15) | 0.0096 (5) | |
C14 | 0.4612 (3) | 0.3667 (2) | 0.69900 (15) | 0.0106 (5) | |
H14A | 0.448566 | 0.397654 | 0.650880 | 0.013* | |
C15 | 0.4086 (3) | 0.4111 (2) | 0.76422 (15) | 0.0099 (5) | |
C16 | 0.4336 (3) | 0.3674 (2) | 0.83453 (15) | 0.0100 (5) | |
H16A | 0.402656 | 0.399307 | 0.880457 | 0.012* | |
C17 | 0.5035 (3) | 0.2771 (2) | 0.83886 (15) | 0.0090 (5) | |
C18 | 0.5510 (3) | 0.2304 (2) | 0.77264 (15) | 0.0092 (5) | |
H18A | 0.595734 | 0.167208 | 0.774895 | 0.011* | |
C19 | 0.3288 (3) | 0.5074 (2) | 0.75636 (16) | 0.0139 (5) | |
C20 | 0.4329 (4) | 0.6272 (3) | 0.73242 (19) | 0.0228 (7) | |
H20A | 0.382906 | 0.689130 | 0.726752 | 0.034* | |
H20B | 0.463592 | 0.604517 | 0.682141 | 0.034* | |
H20C | 0.518497 | 0.664220 | 0.773123 | 0.034* | |
C21 | 0.1958 (3) | 0.4478 (3) | 0.69226 (18) | 0.0243 (7) | |
H21A | 0.131693 | 0.369865 | 0.706788 | 0.036* | |
H21B | 0.227761 | 0.427582 | 0.641934 | 0.036* | |
H21C | 0.142904 | 0.507698 | 0.687084 | 0.036* | |
C22 | 0.2771 (3) | 0.5445 (3) | 0.83319 (17) | 0.0162 (6) | |
H22A | 0.208836 | 0.468930 | 0.847978 | 0.024* | |
H22B | 0.228501 | 0.606900 | 0.825887 | 0.024* | |
H22C | 0.360949 | 0.581275 | 0.874997 | 0.024* | |
C23 | 0.5353 (3) | 0.2327 (2) | 0.91271 (15) | 0.0088 (5) | |
C24 | 0.6564 (3) | 0.1682 (2) | 1.00576 (15) | 0.0091 (5) | |
C25 | 0.7573 (3) | 0.1319 (2) | 1.05176 (15) | 0.0112 (5) | |
H25A | 0.847917 | 0.133746 | 1.036094 | 0.013* | |
C26 | 0.7169 (3) | 0.0929 (2) | 1.12160 (16) | 0.0127 (5) | |
H26A | 0.782433 | 0.068395 | 1.155286 | 0.015* | |
C27 | 0.5816 (3) | 0.0886 (2) | 1.14430 (15) | 0.0126 (5) | |
H27A | 0.558408 | 0.060958 | 1.192707 | 0.015* | |
C28 | 0.4818 (3) | 0.1234 (2) | 1.09797 (15) | 0.0104 (5) | |
H28A | 0.390052 | 0.119514 | 1.112863 | 0.013* | |
C29 | 0.5231 (3) | 0.1643 (2) | 1.02846 (15) | 0.0086 (5) | |
C30 | 0.3016 (3) | 0.2106 (2) | 0.96844 (15) | 0.0097 (5) | |
H30A | 0.239454 | 0.132290 | 0.984765 | 0.012* | |
H30B | 0.260795 | 0.213677 | 0.914165 | 0.012* | |
C31 | 0.2987 (3) | 0.3254 (2) | 1.02351 (15) | 0.0116 (5) | |
H31A | 0.366003 | 0.403763 | 1.009825 | 0.014* | |
H31B | 0.331720 | 0.319240 | 1.078541 | 0.014* | |
C32 | 0.1447 (3) | 0.3319 (3) | 1.01653 (17) | 0.0153 (6) | |
H32A | 0.117316 | 0.347650 | 0.962901 | 0.018* | |
H32B | 0.076545 | 0.248586 | 1.023004 | 0.018* | |
C33 | 0.1271 (3) | 0.4344 (3) | 1.07662 (18) | 0.0209 (6) | |
H33A | 0.198659 | 0.517088 | 1.071842 | 0.025* | |
H33B | 0.028751 | 0.439720 | 1.063744 | 0.025* | |
C34 | 0.1476 (4) | 0.4122 (3) | 1.16171 (19) | 0.0294 (7) | |
H34A | 0.123242 | 0.475748 | 1.196056 | 0.044* | |
H34B | 0.249058 | 0.419258 | 1.177643 | 0.044* | |
H34C | 0.083626 | 0.327163 | 1.166161 | 0.044* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Hg | 0.01221 (6) | 0.01533 (7) | 0.01315 (6) | 0.00693 (5) | −0.00075 (4) | 0.00220 (4) |
Cl1 | 0.0100 (3) | 0.0128 (3) | 0.0126 (3) | 0.0058 (2) | −0.0012 (2) | −0.0006 (2) |
Cl2 | 0.0157 (3) | 0.0210 (3) | 0.0217 (3) | 0.0007 (3) | −0.0083 (3) | 0.0010 (3) |
Cl3 | 0.0168 (3) | 0.0241 (4) | 0.0258 (4) | 0.0097 (3) | 0.0075 (3) | 0.0008 (3) |
Cl4 | 0.0176 (3) | 0.0293 (4) | 0.0191 (3) | 0.0108 (3) | 0.0016 (3) | 0.0121 (3) |
N1 | 0.0104 (10) | 0.0146 (11) | 0.0073 (10) | 0.0067 (9) | −0.0015 (8) | 0.0027 (8) |
N2 | 0.0096 (10) | 0.0109 (11) | 0.0087 (10) | 0.0056 (9) | −0.0003 (8) | 0.0019 (8) |
N3 | 0.0082 (10) | 0.0088 (10) | 0.0088 (10) | 0.0046 (8) | −0.0010 (8) | 0.0016 (8) |
N4 | 0.0084 (10) | 0.0107 (11) | 0.0102 (11) | 0.0046 (9) | 0.0018 (8) | 0.0024 (8) |
C1 | 0.0114 (12) | 0.0061 (12) | 0.0102 (12) | 0.0030 (10) | −0.0008 (10) | 0.0033 (9) |
C2 | 0.0105 (12) | 0.0097 (12) | 0.0120 (13) | 0.0042 (10) | 0.0005 (10) | 0.0016 (10) |
C3 | 0.0109 (13) | 0.0167 (14) | 0.0173 (14) | 0.0064 (11) | 0.0010 (11) | 0.0040 (11) |
C4 | 0.0144 (13) | 0.0195 (15) | 0.0212 (15) | 0.0082 (12) | 0.0064 (11) | 0.0026 (12) |
C5 | 0.0231 (15) | 0.0205 (15) | 0.0123 (14) | 0.0094 (12) | 0.0044 (11) | 0.0002 (11) |
C6 | 0.0189 (14) | 0.0208 (15) | 0.0102 (13) | 0.0105 (12) | −0.0012 (11) | 0.0020 (11) |
C7 | 0.0124 (13) | 0.0101 (12) | 0.0124 (13) | 0.0052 (10) | 0.0017 (10) | 0.0022 (10) |
C8 | 0.007 (3) | 0.0168 (16) | 0.008 (5) | 0.0046 (19) | −0.001 (3) | 0.002 (2) |
C9 | 0.009 (2) | 0.016 (4) | 0.014 (3) | 0.003 (2) | −0.002 (2) | 0.005 (3) |
C10 | 0.008 (2) | 0.017 (4) | 0.017 (3) | 0.003 (3) | −0.0042 (17) | 0.003 (3) |
C11 | 0.015 (2) | 0.037 (4) | 0.050 (4) | 0.009 (3) | −0.003 (2) | 0.026 (3) |
C12 | 0.021 (3) | 0.046 (5) | 0.070 (5) | 0.010 (3) | −0.007 (3) | 0.036 (4) |
C8A | 0.007 (3) | 0.0168 (16) | 0.008 (5) | 0.0046 (19) | −0.001 (3) | 0.002 (2) |
C9A | 0.009 (2) | 0.016 (4) | 0.014 (3) | 0.003 (2) | −0.002 (2) | 0.005 (3) |
C10A | 0.008 (2) | 0.017 (4) | 0.017 (3) | 0.003 (3) | −0.0042 (17) | 0.003 (3) |
C11A | 0.015 (2) | 0.037 (4) | 0.050 (4) | 0.009 (3) | −0.003 (2) | 0.026 (3) |
C12A | 0.021 (3) | 0.046 (5) | 0.070 (5) | 0.010 (3) | −0.007 (3) | 0.036 (4) |
C13 | 0.0081 (12) | 0.0084 (12) | 0.0105 (12) | 0.0014 (10) | −0.0007 (10) | 0.0004 (10) |
C14 | 0.0112 (12) | 0.0098 (12) | 0.0113 (13) | 0.0039 (10) | −0.0007 (10) | 0.0043 (10) |
C15 | 0.0094 (12) | 0.0067 (12) | 0.0135 (13) | 0.0028 (10) | 0.0006 (10) | 0.0024 (10) |
C16 | 0.0102 (12) | 0.0077 (12) | 0.0111 (13) | 0.0022 (10) | 0.0010 (10) | 0.0003 (10) |
C17 | 0.0075 (12) | 0.0072 (12) | 0.0101 (12) | 0.0004 (10) | −0.0019 (9) | 0.0018 (10) |
C18 | 0.0068 (12) | 0.0076 (12) | 0.0128 (13) | 0.0025 (10) | −0.0012 (10) | 0.0023 (10) |
C19 | 0.0182 (14) | 0.0101 (13) | 0.0174 (14) | 0.0095 (11) | 0.0030 (11) | 0.0042 (10) |
C20 | 0.0355 (18) | 0.0146 (14) | 0.0269 (16) | 0.0148 (13) | 0.0148 (14) | 0.0104 (12) |
C21 | 0.0270 (16) | 0.0317 (17) | 0.0223 (16) | 0.0234 (14) | −0.0040 (13) | 0.0036 (13) |
C22 | 0.0211 (14) | 0.0128 (13) | 0.0211 (15) | 0.0118 (12) | 0.0075 (12) | 0.0060 (11) |
C23 | 0.0097 (12) | 0.0047 (12) | 0.0106 (12) | 0.0017 (10) | −0.0005 (10) | −0.0001 (9) |
C24 | 0.0122 (12) | 0.0054 (12) | 0.0090 (12) | 0.0037 (10) | −0.0013 (10) | −0.0007 (9) |
C25 | 0.0107 (12) | 0.0100 (13) | 0.0136 (13) | 0.0060 (10) | −0.0012 (10) | 0.0004 (10) |
C26 | 0.0156 (13) | 0.0093 (13) | 0.0132 (13) | 0.0063 (11) | −0.0044 (10) | 0.0009 (10) |
C27 | 0.0185 (14) | 0.0093 (12) | 0.0099 (13) | 0.0047 (11) | 0.0010 (10) | 0.0021 (10) |
C28 | 0.0132 (13) | 0.0079 (12) | 0.0099 (12) | 0.0042 (10) | 0.0011 (10) | −0.0006 (10) |
C29 | 0.0100 (12) | 0.0057 (12) | 0.0091 (12) | 0.0033 (10) | −0.0030 (9) | −0.0011 (9) |
C30 | 0.0049 (12) | 0.0120 (13) | 0.0128 (13) | 0.0037 (10) | −0.0008 (9) | 0.0031 (10) |
C31 | 0.0096 (12) | 0.0130 (13) | 0.0124 (13) | 0.0050 (10) | −0.0003 (10) | 0.0014 (10) |
C32 | 0.0121 (13) | 0.0146 (14) | 0.0204 (14) | 0.0070 (11) | −0.0007 (11) | 0.0027 (11) |
C33 | 0.0188 (15) | 0.0177 (15) | 0.0300 (17) | 0.0121 (12) | 0.0044 (12) | 0.0011 (12) |
C34 | 0.0379 (19) | 0.0280 (17) | 0.0275 (17) | 0.0191 (15) | 0.0084 (14) | −0.0012 (14) |
Hg—Cl4 | 2.4120 (9) | C11A—H11C | 0.9900 |
Hg—Cl3 | 2.4171 (11) | C11A—H11D | 0.9900 |
Hg—Cl2 | 2.4716 (12) | C12A—H12D | 0.9800 |
Hg—Cl1 | 2.6579 (13) | C12A—H12E | 0.9800 |
Cl4—Cl4i | 3.4343 (16) | C12A—H12F | 0.9800 |
N1—C1 | 1.336 (3) | C13—C14 | 1.393 (4) |
N1—C2 | 1.386 (3) | C13—C18 | 1.393 (4) |
N1—H1A | 0.8800 | C14—C15 | 1.392 (4) |
N2—C1 | 1.347 (3) | C14—H14A | 0.9500 |
N2—C7 | 1.390 (3) | C15—C16 | 1.391 (4) |
N2—C8A | 1.468 (17) | C15—C19 | 1.536 (3) |
N2—C8 | 1.51 (5) | C16—C17 | 1.400 (4) |
N3—C23 | 1.340 (3) | C16—H16A | 0.9500 |
N3—C29 | 1.401 (3) | C17—C18 | 1.388 (4) |
N3—C30 | 1.477 (3) | C17—C23 | 1.464 (4) |
N4—C23 | 1.339 (3) | C18—H18A | 0.9500 |
N4—C24 | 1.392 (3) | C19—C22 | 1.528 (4) |
N4—H4B | 0.8800 | C19—C21 | 1.533 (4) |
C1—C13 | 1.460 (4) | C19—C20 | 1.540 (4) |
C2—C3 | 1.394 (4) | C20—H20A | 0.9800 |
C2—C7 | 1.396 (4) | C20—H20B | 0.9800 |
C3—C4 | 1.380 (4) | C20—H20C | 0.9800 |
C3—H3A | 0.9500 | C21—H21A | 0.9800 |
C4—C5 | 1.407 (4) | C21—H21B | 0.9800 |
C4—H4A | 0.9500 | C21—H21C | 0.9800 |
C5—C6 | 1.379 (4) | C22—H22A | 0.9800 |
C5—H5A | 0.9500 | C22—H22B | 0.9800 |
C6—C7 | 1.394 (4) | C22—H22C | 0.9800 |
C6—H6A | 0.9500 | C24—C29 | 1.392 (4) |
C8—C9 | 1.524 (16) | C24—C25 | 1.396 (4) |
C8—H8A | 0.9599 | C25—C26 | 1.384 (4) |
C8—H8B | 0.9600 | C25—H25A | 0.9500 |
C9—C10 | 1.532 (15) | C26—C27 | 1.409 (4) |
C9—H9A | 0.9900 | C26—H26A | 0.9500 |
C9—H9B | 0.9900 | C27—C28 | 1.382 (4) |
C10—C11 | 1.529 (15) | C27—H27A | 0.9500 |
C10—H10A | 0.9900 | C28—C29 | 1.389 (4) |
C10—H10B | 0.9900 | C28—H28A | 0.9500 |
C11—C12 | 1.526 (15) | C30—C31 | 1.523 (4) |
C11—H11A | 0.9900 | C30—H30A | 0.9900 |
C11—H11B | 0.9900 | C30—H30B | 0.9900 |
C12—H12A | 0.9800 | C31—C32 | 1.528 (4) |
C12—H12B | 0.9800 | C31—H31A | 0.9900 |
C12—H12C | 0.9800 | C31—H31B | 0.9900 |
C8A—C9A | 1.525 (8) | C32—C33 | 1.524 (4) |
C8A—H8AA | 0.9599 | C32—H32A | 0.9900 |
C8A—H8AB | 0.9600 | C32—H32B | 0.9900 |
C9A—C10A | 1.527 (6) | C33—C34 | 1.524 (5) |
C9A—H9AA | 0.9900 | C33—H33A | 0.9900 |
C9A—H9AB | 0.9900 | C33—H33B | 0.9900 |
C10A—C11A | 1.518 (6) | C34—H34A | 0.9800 |
C10A—H10C | 0.9900 | C34—H34B | 0.9800 |
C10A—H10D | 0.9900 | C34—H34C | 0.9800 |
C11A—C12A | 1.518 (6) | ||
Cl4—Hg—Cl3 | 120.68 (3) | H12D—C12A—H12E | 109.5 |
Cl4—Hg—Cl2 | 108.75 (3) | C11A—C12A—H12F | 109.5 |
Cl3—Hg—Cl2 | 120.54 (4) | H12D—C12A—H12F | 109.5 |
Cl4—Hg—Cl1 | 102.32 (3) | H12E—C12A—H12F | 109.5 |
Cl3—Hg—Cl1 | 101.25 (3) | C14—C13—C18 | 120.3 (2) |
Cl2—Hg—Cl1 | 98.16 (3) | C14—C13—C1 | 121.9 (2) |
Hg—Cl4—Cl4i | 146.10 (4) | C18—C13—C1 | 117.7 (2) |
C1—N1—C2 | 109.6 (2) | C15—C14—C13 | 121.4 (2) |
C1—N1—H1A | 125.2 | C15—C14—H14A | 119.3 |
C2—N1—H1A | 125.2 | C13—C14—H14A | 119.3 |
C1—N2—C7 | 108.4 (2) | C16—C15—C14 | 117.8 (2) |
C1—N2—C8A | 128.6 (11) | C16—C15—C19 | 122.9 (2) |
C7—N2—C8A | 122.9 (12) | C14—C15—C19 | 119.2 (2) |
C1—N2—C8 | 123 (3) | C15—C16—C17 | 121.2 (2) |
C7—N2—C8 | 128 (3) | C15—C16—H16A | 119.4 |
C23—N3—C29 | 108.6 (2) | C17—C16—H16A | 119.4 |
C23—N3—C30 | 127.4 (2) | C18—C17—C16 | 120.3 (2) |
C29—N3—C30 | 123.9 (2) | C18—C17—C23 | 117.5 (2) |
C23—N4—C24 | 109.2 (2) | C16—C17—C23 | 122.2 (2) |
C23—N4—H4B | 125.4 | C17—C18—C13 | 118.9 (2) |
C24—N4—H4B | 125.4 | C17—C18—H18A | 120.6 |
N1—C1—N2 | 109.0 (2) | C13—C18—H18A | 120.6 |
N1—C1—C13 | 122.6 (2) | C22—C19—C21 | 108.6 (2) |
N2—C1—C13 | 128.3 (2) | C22—C19—C15 | 112.1 (2) |
N1—C2—C3 | 132.0 (2) | C21—C19—C15 | 108.5 (2) |
N1—C2—C7 | 106.0 (2) | C22—C19—C20 | 109.1 (2) |
C3—C2—C7 | 122.0 (2) | C21—C19—C20 | 109.8 (2) |
C4—C3—C2 | 115.9 (2) | C15—C19—C20 | 108.7 (2) |
C4—C3—H3A | 122.1 | C19—C20—H20A | 109.5 |
C2—C3—H3A | 122.1 | C19—C20—H20B | 109.5 |
C3—C4—C5 | 122.2 (3) | H20A—C20—H20B | 109.5 |
C3—C4—H4A | 118.9 | C19—C20—H20C | 109.5 |
C5—C4—H4A | 118.9 | H20A—C20—H20C | 109.5 |
C6—C5—C4 | 121.8 (3) | H20B—C20—H20C | 109.5 |
C6—C5—H5A | 119.1 | C19—C21—H21A | 109.5 |
C4—C5—H5A | 119.1 | C19—C21—H21B | 109.5 |
C5—C6—C7 | 116.2 (3) | H21A—C21—H21B | 109.5 |
C5—C6—H6A | 121.9 | C19—C21—H21C | 109.5 |
C7—C6—H6A | 121.9 | H21A—C21—H21C | 109.5 |
N2—C7—C6 | 131.1 (2) | H21B—C21—H21C | 109.5 |
N2—C7—C2 | 107.1 (2) | C19—C22—H22A | 109.5 |
C6—C7—C2 | 121.8 (2) | C19—C22—H22B | 109.5 |
N2—C8—C9 | 112 (4) | H22A—C22—H22B | 109.5 |
N2—C8—H8A | 113.5 | C19—C22—H22C | 109.5 |
C9—C8—H8A | 116.9 | H22A—C22—H22C | 109.5 |
N2—C8—H8B | 109.3 | H22B—C22—H22C | 109.5 |
C9—C8—H8B | 96.3 | N4—C23—N3 | 109.2 (2) |
H8A—C8—H8B | 107.2 | N4—C23—C17 | 122.9 (2) |
C8—C9—C10 | 110 (2) | N3—C23—C17 | 127.9 (2) |
C8—C9—H9A | 109.6 | N4—C24—C29 | 106.4 (2) |
C10—C9—H9A | 109.6 | N4—C24—C25 | 131.6 (2) |
C8—C9—H9B | 109.6 | C29—C24—C25 | 122.0 (2) |
C10—C9—H9B | 109.6 | C26—C25—C24 | 115.8 (2) |
H9A—C9—H9B | 108.1 | C26—C25—H25A | 122.1 |
C11—C10—C9 | 111.3 (18) | C24—C25—H25A | 122.1 |
C11—C10—H10A | 109.4 | C25—C26—C27 | 122.0 (2) |
C9—C10—H10A | 109.4 | C25—C26—H26A | 119.0 |
C11—C10—H10B | 109.4 | C27—C26—H26A | 119.0 |
C9—C10—H10B | 109.4 | C28—C27—C26 | 121.7 (2) |
H10A—C10—H10B | 108.0 | C28—C27—H27A | 119.1 |
C12—C11—C10 | 111.1 (15) | C26—C27—H27A | 119.1 |
C12—C11—H11A | 109.4 | C27—C28—C29 | 116.3 (2) |
C10—C11—H11A | 109.4 | C27—C28—H28A | 121.8 |
C12—C11—H11B | 109.4 | C29—C28—H28A | 121.8 |
C10—C11—H11B | 109.4 | C28—C29—C24 | 122.1 (2) |
H11A—C11—H11B | 108.0 | C28—C29—N3 | 131.4 (2) |
C11—C12—H12A | 109.5 | C24—C29—N3 | 106.6 (2) |
C11—C12—H12B | 109.5 | N3—C30—C31 | 111.9 (2) |
H12A—C12—H12B | 109.5 | N3—C30—H30A | 109.2 |
C11—C12—H12C | 109.5 | C31—C30—H30A | 109.2 |
H12A—C12—H12C | 109.5 | N3—C30—H30B | 109.2 |
H12B—C12—H12C | 109.5 | C31—C30—H30B | 109.2 |
N2—C8A—C9A | 112.4 (13) | H30A—C30—H30B | 107.9 |
N2—C8A—H8AA | 107.8 | C30—C31—C32 | 110.1 (2) |
C9A—C8A—H8AA | 106.1 | C30—C31—H31A | 109.6 |
N2—C8A—H8AB | 108.8 | C32—C31—H31A | 109.6 |
C9A—C8A—H8AB | 113.3 | C30—C31—H31B | 109.6 |
H8AA—C8A—H8AB | 108.3 | C32—C31—H31B | 109.6 |
C8A—C9A—C10A | 110.8 (7) | H31A—C31—H31B | 108.1 |
C8A—C9A—H9AA | 109.5 | C33—C32—C31 | 113.9 (2) |
C10A—C9A—H9AA | 109.5 | C33—C32—H32A | 108.8 |
C8A—C9A—H9AB | 109.5 | C31—C32—H32A | 108.8 |
C10A—C9A—H9AB | 109.5 | C33—C32—H32B | 108.8 |
H9AA—C9A—H9AB | 108.1 | C31—C32—H32B | 108.8 |
C11A—C10A—C9A | 113.0 (6) | H32A—C32—H32B | 107.7 |
C11A—C10A—H10C | 109.0 | C34—C33—C32 | 114.2 (2) |
C9A—C10A—H10C | 109.0 | C34—C33—H33A | 108.7 |
C11A—C10A—H10D | 109.0 | C32—C33—H33A | 108.7 |
C9A—C10A—H10D | 109.0 | C34—C33—H33B | 108.7 |
H10C—C10A—H10D | 107.8 | C32—C33—H33B | 108.7 |
C12A—C11A—C10A | 113.2 (5) | H33A—C33—H33B | 107.6 |
C12A—C11A—H11C | 108.9 | C33—C34—H34A | 109.5 |
C10A—C11A—H11C | 108.9 | C33—C34—H34B | 109.5 |
C12A—C11A—H11D | 108.9 | H34A—C34—H34B | 109.5 |
C10A—C11A—H11D | 108.9 | C33—C34—H34C | 109.5 |
H11C—C11A—H11D | 107.7 | H34A—C34—H34C | 109.5 |
C11A—C12A—H12D | 109.5 | H34B—C34—H34C | 109.5 |
C11A—C12A—H12E | 109.5 | ||
C2—N1—C1—N2 | −0.7 (3) | C19—C15—C16—C17 | 178.4 (2) |
C2—N1—C1—C13 | 178.7 (2) | C15—C16—C17—C18 | 0.8 (4) |
C7—N2—C1—N1 | 0.2 (3) | C15—C16—C17—C23 | 177.9 (2) |
C8A—N2—C1—N1 | 175.5 (10) | C16—C17—C18—C13 | 2.0 (4) |
C8—N2—C1—N1 | 173 (3) | C23—C17—C18—C13 | −175.4 (2) |
C7—N2—C1—C13 | −179.2 (2) | C14—C13—C18—C17 | −2.5 (4) |
C8A—N2—C1—C13 | −3.9 (11) | C1—C13—C18—C17 | 173.2 (2) |
C8—N2—C1—C13 | −7 (3) | C16—C15—C19—C22 | −1.9 (4) |
C1—N1—C2—C3 | −177.2 (3) | C14—C15—C19—C22 | 179.3 (2) |
C1—N1—C2—C7 | 0.9 (3) | C16—C15—C19—C21 | −121.9 (3) |
N1—C2—C3—C4 | 178.6 (3) | C14—C15—C19—C21 | 59.4 (3) |
C7—C2—C3—C4 | 0.8 (4) | C16—C15—C19—C20 | 118.8 (3) |
C2—C3—C4—C5 | 0.3 (4) | C14—C15—C19—C20 | −60.0 (3) |
C3—C4—C5—C6 | −1.0 (5) | C24—N4—C23—N3 | 0.3 (3) |
C4—C5—C6—C7 | 0.7 (4) | C24—N4—C23—C17 | −179.1 (2) |
C1—N2—C7—C6 | 178.9 (3) | C29—N3—C23—N4 | −0.5 (3) |
C8A—N2—C7—C6 | 3.3 (10) | C30—N3—C23—N4 | −176.8 (2) |
C8—N2—C7—C6 | 7 (3) | C29—N3—C23—C17 | 178.8 (2) |
C1—N2—C7—C2 | 0.4 (3) | C30—N3—C23—C17 | 2.5 (4) |
C8A—N2—C7—C2 | −175.3 (9) | C18—C17—C23—N4 | 37.0 (3) |
C8—N2—C7—C2 | −172 (2) | C16—C17—C23—N4 | −140.3 (3) |
C5—C6—C7—N2 | −178.0 (3) | C18—C17—C23—N3 | −142.3 (3) |
C5—C6—C7—C2 | 0.4 (4) | C16—C17—C23—N3 | 40.4 (4) |
N1—C2—C7—N2 | −0.8 (3) | C23—N4—C24—C29 | 0.1 (3) |
C3—C2—C7—N2 | 177.6 (2) | C23—N4—C24—C25 | 179.3 (3) |
N1—C2—C7—C6 | −179.5 (2) | N4—C24—C25—C26 | −179.7 (3) |
C3—C2—C7—C6 | −1.2 (4) | C29—C24—C25—C26 | −0.6 (4) |
C1—N2—C8—C9 | 115 (5) | C24—C25—C26—C27 | 0.9 (4) |
C7—N2—C8—C9 | −74 (6) | C25—C26—C27—C28 | −0.2 (4) |
N2—C8—C9—C10 | 175 (4) | C26—C27—C28—C29 | −0.8 (4) |
C8—C9—C10—C11 | 177 (4) | C27—C28—C29—C24 | 1.1 (4) |
C9—C10—C11—C12 | −178 (3) | C27—C28—C29—N3 | −179.8 (2) |
C1—N2—C8A—C9A | 102.1 (16) | N4—C24—C29—C28 | 178.9 (2) |
C7—N2—C8A—C9A | −83 (2) | C25—C24—C29—C28 | −0.4 (4) |
N2—C8A—C9A—C10A | −175.0 (15) | N4—C24—C29—N3 | −0.4 (3) |
C8A—C9A—C10A—C11A | 179.7 (15) | C25—C24—C29—N3 | −179.7 (2) |
C9A—C10A—C11A—C12A | −178.1 (9) | C23—N3—C29—C28 | −178.6 (3) |
N1—C1—C13—C14 | 136.1 (3) | C30—N3—C29—C28 | −2.2 (4) |
N2—C1—C13—C14 | −44.6 (4) | C23—N3—C29—C24 | 0.6 (3) |
N1—C1—C13—C18 | −39.6 (4) | C30—N3—C29—C24 | 177.0 (2) |
N2—C1—C13—C18 | 139.8 (3) | C23—N3—C30—C31 | −105.7 (3) |
C18—C13—C14—C15 | 0.3 (4) | C29—N3—C30—C31 | 78.5 (3) |
C1—C13—C14—C15 | −175.2 (2) | N3—C30—C31—C32 | 175.7 (2) |
C13—C14—C15—C16 | 2.3 (4) | C30—C31—C32—C33 | 173.0 (2) |
C13—C14—C15—C19 | −178.8 (2) | C31—C32—C33—C34 | −65.8 (3) |
C14—C15—C16—C17 | −2.9 (4) |
Symmetry code: (i) −x+2, −y, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···Cl1 | 0.88 | 2.30 | 3.171 (2) | 171 |
N4—H4B···Cl1 | 0.88 | 2.35 | 3.224 (2) | 170 |
C3—H3A···Cl3 | 0.95 | 2.90 | 3.803 (3) | 160 |
C6—H6A···Cl2ii | 0.95 | 2.56 | 3.492 (3) | 169 |
C18—H18A···Cl1 | 0.95 | 2.85 | 3.331 (4) | 113 |
C25—H25A···Cl4i | 0.95 | 2.96 | 3.664 (3) | 132 |
C28—H28A···Cl4iii | 0.95 | 2.91 | 3.796 (3) | 156 |
C30—H30A···Cl4iii | 0.99 | 2.77 | 3.627 (3) | 145 |
Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+1, −y, −z+1; (iii) −x+1, −y, −z+2. |
Acknowledgements
RJB is grateful for NSF award 1205608, Partnership for Reduced Dimensional Materials, for partial funding of this research, and the Howard University Nanoscience Facility access to liquid nitrogen. The authors wish to acknowledge the assistance of Dr Matthias Zeller in the collection of diffraction data and NSF Grant DMR 1337296 for funds to purchase the X-ray diffractometer. HBS is grateful to the DST, New Delhi, for a J. C. Bose National Fellowship. VR gratefully acknowledges the Council of Scientific and Industrial Research (CSIR), New Delhi for an SRF.
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