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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): m848–m849.
Published online 2009 July 1. doi:  10.1107/S1600536809024180
PMCID: PMC2977193

Dichlorido(2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline-κ2 N,N′)mercury(II) acetonitrile hemisolvate

Abstract

The asymmetric unit of the title compound, [HgCl2(C26H20N2)]·0.5CH3CN, contains two crystallographic­ally independent [HgCl2(C26H20N2)] mol­ecules and one acetonitrile solvent mol­ecule. The HgII atoms are four-coordin­ated in distorted tetra­hedral configurations by two N atoms from 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline ligands and two Cl atoms. The ligand ring systems are not planar. The phenyl rings are oriented at dihedral angles of 74.61 (3) and 66.00 (3)° in the two molecules. In the crystal structure, π–π contacts between phenanthroline rings [centroid–centroid distances = 3.809 (1), 3.686 (1), 3.986 (1), 3.877 (1), 3.697 (1), 3.789 (1), 3.745 (1), 3.797 (1) and 3.638 (1) Å] may stabilize the structure.

Related literature

For HgII X 2 complexes (X=Br, Cl, I and SCN) with bidentate N,N′ donor sets, see: Ahmadi et al. (2008 [triangle]); Alizadeh (2009 [triangle]); Hughes et al. (1985 [triangle]); Kalateh et al. (2008 [triangle]); Khoshtarkib et al. (2009 [triangle]); Mahjoub & Morsali (2003 [triangle]); Morsali (2006 [triangle]); Morsali et al. (2003 [triangle], 2004 [triangle]); Safari et al. (2009 [triangle]); Tadayon Pour et al. (2008 [triangle]); Xie et al. (2004 [triangle]); Yousefi et al. (2009 [triangle]); Yousefi, Rashidi Vahid et al. (2008 [triangle]); Yousefi, Tadayon Pour et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0m848-scheme1.jpg

Experimental

Crystal data

  • [HgCl2(C26H20N2)]·0.5C2H3N
  • M r = 652.46
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0m848-efi1.jpg
  • a = 11.7514 (6) Å
  • b = 14.1283 (7) Å
  • c = 16.1311 (8) Å
  • α = 107.537 (4)°
  • β = 101.924 (4)°
  • γ = 100.138 (4)°
  • V = 2415.8 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 6.61 mm−1
  • T = 120 K
  • 0.50 × 0.13 × 0.11 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 1998 [triangle]) T min = 0.379, T max = 0.479
  • 27210 measured reflections
  • 12974 independent reflections
  • 11253 reflections with I > 2σ(I)
  • R int = 0.040

Refinement

  • R[F 2 > 2σ(F 2)] = 0.033
  • wR(F 2) = 0.074
  • S = 1.06
  • 12974 reflections
  • 586 parameters
  • H-atom parameters constrained
  • Δρmax = 1.80 e Å−3
  • Δρmin = −1.65 e Å−3

Data collection: SMART (Bruker, 1998 [triangle]); cell refinement: SAINT (Bruker, 1998 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Selected geometric parameters (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809024180/hk2718sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024180/hk2718Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We are grateful to Damghan University of Basic Sciences and Islamic Azad University, Shahr-e-Rey Branch, for financial support.

supplementary crystallographic information

Comment

There are several HgII complexes, with formula, [Hg(N—N)X2], (X=Br, Cl, I and SCN), such as [Hg(2,9-dmphen)Br2], (II), (Khoshtarkib et al., 2009), [Hg(ph2dmphen)SCN2], (III), (Alizadeh 2009), [Hg(TPA)Br2], (IV), (Xie et al., 2004), [Hg(TPD)Br2], (V), (Hughes et al., 1985), [Hg(NH(py)2)Br2], (VI), (Kalateh et al., 2008), [Hg(6-mbpy)Cl2], (VII), (Ahmadi et al., 2008), [Hg(NH(py)2)Cl2], (VIII), (Yousefi et al., 2009), [Hg(4,4'-dmbpy)I2], (IX), (Yousefi, Tadayon Pour et al., 2008), [Hg(5,5'-dmbpy)I2], (X), (Tadayon Pour et al., 2008), [Hg(ph2phen)I2], (XI), (Yousefi, Rashidi Vahid et al., 2008), [Hg(SCN)2(TBI)], (XII), (Morsali 2006), [Hg (dp4bt)(SCN)2], (XIII), (Mahjoub & Morsali 2003), [Hg(da4bt)(SCN)2], (XIV), (Morsali et al., 2003), [Hg(biq)(SCN)2].C6H6, (XV), (Morsali et al., 2004) and [Hg(dm4bt)(SCN)2], (XVI), (Safari et al., 2009) [where 2,9-dmphen is 2,9-dimethyl-1,10-phenanthroline, ph2dmphen is 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, TPA is tris(2-pyridyl)amine, TPD is N,N,N',N'-Tetramethyl-o-phenylenediamine, NH(py)2 is di-2-pyridylamine, 6-mbpy is 6-methyl-2,2'-bipyridine, 4,4'-dmbpy is 4,4'-dimethyl-2,2'-bipyridine, 5,5'-dmbpy is 5,5'-dimethyl-2,2'-bipyridine, ph2phen is 4,7-diphenyl-1,10-phenanthroline, TBI is 4,4',5,5'-tetramethyl-2,2'-bi-imidazole, dp4bt is 2,2'-diphenyl-4,4'-bithiazole, da4bt is 2,2'-diamino-4,4'-bithiazole, biq is 2,2'-biquinoline and dm4bt is 2,2'-dimethyl-4,4'-bithiazole] have been synthesized and characterized by single-crystal X-ray diffraction methods. We report herein the synthesis and crystal structure of the title compound, (I).

The asymmetric unit of the title compound, (I), (Fig. 1) contains two crystallographically independent [HgCl2(C26H20N2)] molecules and one acetonitrile solvent molecule. The HgII atoms are four-coordinated in distorted tetrahedral configurations by two N atoms from 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline and two Cl atoms (Table 1). Rings A (N1/C2-C4/C11/C26), B (C11-C14/C25/C26), C (N2/C14/C15/C22/C23/C25) and F (N3/C28-C30/C37/C52), G (C37-C40/C51/C52), H (N4/C40/C41/C48/C49/C51) are, of course, planar and the dihedral angles between them are A/B = 4.00 (3), A/C = 6.08 (3), B/C = 3.52 (3) and F/G = 5.77 (3), F/H = 5.55 (3), G/H = 3.53 (3) °. So, the phenanthroline ring systems are not planar. The phenyl rings D (C5-C10), E (C16-C21) and I (C31-C36), J (C42-C47) are oriented at dihedral angles of D/E = 74.61 (3) and I/J = 66.00 (3) °.

In the crystal structure (Fig. 2), the π–π contacts between the phenanthroline rings, Cg1—Cg2i, Cg2—Cg2i, Cg1—Cg3i, Cg2—Cg9ii, Cg6—Cg7iii, Cg6—Cg8iii, Cg7—Cg7iii, Cg11—Cg2i and Cg12—Cg7iii, [symmetry codes: (i) 2 - x, 1 - y, -z, (ii) 2 - x, 1 - y, 1 - z, (iii) 2 - x, -y, 1 - z, where Cg1, Cg2, Cg3, Cg6, Cg7, Cg8, Cg9, Cg11 and Cg12 are centroids of the rings A (N1/C2-C4/C11/C26), B (C11-C14/C25/C26), C (N2/C14/C15/C22/C23/C25), F (N3/C28-C30/C37/C52), G (C37-C40/C51/C52), H (N4/C40/C41/C48/C49/C51), I (C31-C36), K (Hg1/N1/N2/C25/C26) and L (Hg2/N3/N4/C51/C52), respectively] may stabilize the structure, with centroid-centroid distances of 3.809 (1), 3.686 (1), 3.986 (1), 3.877 (1), 3.697 (1), 3.789 (1), 3.745 (1), 3.797 (1) and 3.638 (1) Å.

Experimental

For the preparation of the title compound, (I), a solution of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (0.36 g, 1.10 mmol) in HCCl3 (20 ml) was added to a solution of HgCl2 (0.30 g, 1.10 mmol) in acetonitrile (20 ml) and the resulting pale yellow solution was stirred for 20 min at room temperature. Then, it was left to evaporate slowly at room temperature. After one week, colorless needle crystals of the title compound were isolated (yield; 0.47 g, 72.0%).

Refinement

H atoms were positioned geometrically, with C-H = 0.93 and 0.96 Å for aromatic and methyl H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 40% probability level.
Fig. 2.
A partial packing diagram of the title compound.

Crystal data

[HgCl2(C26H20N2)]·0.5C2H3NZ = 4
Mr = 652.46F(000) = 1260
Triclinic, P1Dx = 1.794 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.7514 (6) ÅCell parameters from 2354 reflections
b = 14.1283 (7) Åθ = 1.7–29.2°
c = 16.1311 (8) ŵ = 6.61 mm1
α = 107.537 (4)°T = 120 K
β = 101.924 (4)°Needle, colorless
γ = 100.138 (4)°0.50 × 0.13 × 0.11 mm
V = 2415.8 (2) Å3

Data collection

Bruker SMART CCD area-detector diffractometer12974 independent reflections
Radiation source: fine-focus sealed tube11253 reflections with I > 2σ(I)
graphiteRint = 0.040
[var phi] and ω scansθmax = 29.2°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 1998)h = −16→15
Tmin = 0.379, Tmax = 0.479k = −14→19
27210 measured reflectionsl = −22→22

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.074H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.0284P)2 + 6.1108P] where P = (Fo2 + 2Fc2)/3
12974 reflections(Δ/σ)max = 0.069
586 parametersΔρmax = 1.80 e Å3
0 restraintsΔρmin = −1.65 e Å3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Hg10.275010 (12)0.652623 (11)0.240510 (10)0.02166 (4)
Hg2−0.094858 (14)−0.153897 (11)0.658801 (11)0.02624 (4)
Cl10.30469 (10)0.75429 (10)0.39530 (8)0.0404 (3)
Cl20.43961 (8)0.62792 (9)0.17808 (7)0.0327 (2)
Cl3−0.17092 (11)−0.11436 (8)0.79185 (8)0.0325 (2)
Cl4−0.01545 (15)−0.30065 (10)0.62270 (10)0.0496 (3)
N10.0961 (3)0.6705 (2)0.1589 (2)0.0177 (6)
N20.1302 (3)0.4968 (2)0.1904 (2)0.0182 (6)
N30.0021 (3)0.0072 (2)0.6640 (2)0.0199 (6)
N4−0.2087 (3)−0.1175 (2)0.5423 (2)0.0223 (6)
N50.4397 (9)0.6246 (9)0.6124 (10)0.148 (5)
C10.1860 (4)0.8503 (3)0.1935 (3)0.0293 (9)
H1A0.25230.83720.16960.035*
H1B0.20920.86480.25760.035*
H1C0.16390.90820.18170.035*
C20.0812 (3)0.7580 (3)0.1493 (3)0.0208 (7)
C3−0.0296 (3)0.7638 (3)0.1013 (3)0.0197 (7)
H3−0.03830.82610.09610.024*
C4−0.1262 (3)0.6783 (3)0.0617 (2)0.0176 (6)
C5−0.2449 (3)0.6878 (3)0.0150 (2)0.0188 (7)
C6−0.2503 (3)0.7394 (3)−0.0462 (3)0.0230 (7)
H6−0.17960.7703−0.05530.028*
C7−0.3607 (4)0.7453 (3)−0.0941 (3)0.0289 (8)
H7−0.36380.7788−0.13580.035*
C8−0.4654 (4)0.7006 (3)−0.0789 (3)0.0337 (10)
H8−0.53950.7024−0.11180.040*
C9−0.4606 (4)0.6536 (3)−0.0155 (3)0.0319 (9)
H9−0.53140.6261−0.00440.038*
C10−0.3521 (3)0.6467 (3)0.0319 (3)0.0217 (7)
H10−0.34990.61510.07480.026*
C11−0.1092 (3)0.5835 (3)0.0690 (2)0.0164 (6)
C12−0.1984 (3)0.4878 (3)0.0245 (2)0.0184 (6)
H12−0.27050.4855−0.01400.022*
C13−0.1803 (3)0.4005 (3)0.0371 (2)0.0179 (6)
H13−0.24010.33960.00680.022*
C14−0.0712 (3)0.3999 (3)0.0961 (2)0.0167 (6)
C15−0.0507 (3)0.3129 (3)0.1169 (2)0.0181 (6)
C16−0.1438 (3)0.2144 (3)0.0843 (2)0.0189 (7)
C17−0.2524 (4)0.2115 (3)0.1062 (3)0.0297 (9)
H17−0.26870.27230.13730.036*
C18−0.3376 (4)0.1181 (3)0.0819 (3)0.0310 (9)
H18−0.40900.11660.09850.037*
C19−0.3150 (4)0.0284 (3)0.0333 (3)0.0273 (8)
H19−0.3719−0.03370.01620.033*
C20−0.2078 (4)0.0306 (3)0.0099 (3)0.0250 (8)
H20−0.1933−0.0299−0.02380.030*
C21−0.1224 (4)0.1227 (3)0.0367 (3)0.0227 (7)
H21−0.04950.12330.02270.027*
C220.0597 (3)0.3222 (3)0.1730 (3)0.0206 (7)
H220.07480.26580.18740.025*
C230.1493 (3)0.4144 (3)0.2088 (3)0.0207 (7)
C240.2690 (4)0.4243 (3)0.2706 (3)0.0296 (9)
H24A0.28070.47620.32830.035*
H24B0.33190.44320.24460.035*
H24C0.27080.35990.27860.035*
C250.0226 (3)0.4915 (3)0.1352 (2)0.0159 (6)
C260.0040 (3)0.5840 (3)0.1205 (2)0.0156 (6)
C270.1631 (4)0.0257 (3)0.7933 (3)0.0278 (8)
H27A0.1831−0.03590.76220.033*
H27B0.10920.01050.82750.033*
H27C0.23520.07570.83340.033*
C280.1038 (3)0.0675 (3)0.7259 (3)0.0207 (7)
C290.1490 (3)0.1676 (3)0.7296 (2)0.0217 (7)
H290.21870.20880.77440.026*
C300.0927 (3)0.2067 (3)0.6684 (2)0.0191 (7)
C310.1353 (3)0.3159 (3)0.6800 (2)0.0213 (7)
C320.2585 (4)0.3629 (3)0.7060 (3)0.0277 (8)
H320.31370.32450.71400.033*
C330.2994 (4)0.4670 (3)0.7202 (3)0.0349 (10)
H330.38150.49750.73740.042*
C340.2177 (5)0.5249 (3)0.7088 (3)0.0347 (10)
H340.24510.59410.71770.042*
C350.0944 (4)0.4795 (3)0.6839 (3)0.0314 (9)
H350.03950.51840.67640.038*
C360.0540 (4)0.3758 (3)0.6703 (3)0.0256 (8)
H36−0.02820.34590.65440.031*
C37−0.0097 (3)0.1394 (3)0.5972 (2)0.0177 (6)
C38−0.0654 (3)0.1650 (3)0.5221 (2)0.0196 (7)
H38−0.03100.22590.51570.024*
C39−0.1681 (3)0.1012 (3)0.4602 (2)0.0201 (7)
H39−0.20310.11940.41190.024*
C40−0.2237 (3)0.0064 (3)0.4677 (2)0.0198 (7)
C41−0.3364 (3)−0.0594 (3)0.4072 (3)0.0234 (7)
C42−0.4089 (3)−0.0290 (3)0.3382 (3)0.0259 (8)
C43−0.4422 (4)0.0639 (4)0.3615 (3)0.0339 (10)
H43−0.41610.10870.42120.041*
C44−0.5136 (4)0.0894 (4)0.2963 (3)0.0393 (11)
H44−0.53760.15010.31290.047*
C45−0.5494 (4)0.0260 (4)0.2071 (3)0.0339 (10)
H45−0.59600.04440.16340.041*
C46−0.5156 (4)−0.0659 (4)0.1825 (3)0.0323 (9)
H46−0.5394−0.10880.12220.039*
C47−0.4465 (3)−0.0941 (3)0.2477 (3)0.0273 (8)
H47−0.4253−0.15610.23110.033*
C48−0.3771 (4)−0.1520 (3)0.4168 (3)0.0283 (8)
H48−0.4494−0.19640.37780.034*
C49−0.3121 (4)−0.1806 (3)0.4842 (3)0.0277 (8)
C50−0.3575 (4)−0.2804 (4)0.4959 (3)0.0371 (10)
H50A−0.3709−0.26710.55460.045*
H50B−0.2990−0.31980.49050.045*
H50C−0.4316−0.31810.45020.045*
C51−0.1652 (3)−0.0261 (3)0.5351 (2)0.0189 (7)
C52−0.0537 (3)0.0409 (3)0.6004 (2)0.0184 (6)
C530.2214 (10)0.5822 (8)0.5133 (7)0.096 (3)
H53C0.20790.53630.45260.115*
H53B0.20490.64590.51190.115*
H53A0.16910.55190.54210.115*
C540.3439 (10)0.6006 (10)0.5628 (10)0.114 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Hg10.01569 (6)0.01918 (7)0.02492 (7)0.00266 (5)0.00219 (5)0.00375 (5)
Hg20.03505 (8)0.02347 (7)0.02754 (8)0.01105 (6)0.01244 (6)0.01467 (6)
Cl10.0311 (5)0.0489 (7)0.0276 (5)0.0045 (5)0.0090 (4)−0.0031 (5)
Cl20.0180 (4)0.0390 (5)0.0308 (5)0.0043 (4)0.0049 (3)0.0007 (4)
Cl30.0474 (6)0.0313 (5)0.0378 (5)0.0249 (4)0.0250 (5)0.0218 (4)
Cl40.0869 (10)0.0407 (6)0.0555 (8)0.0402 (7)0.0473 (7)0.0331 (6)
N10.0149 (12)0.0151 (13)0.0240 (15)0.0037 (10)0.0062 (11)0.0078 (11)
N20.0163 (13)0.0166 (13)0.0203 (14)0.0054 (11)0.0030 (11)0.0050 (11)
N30.0215 (14)0.0210 (14)0.0213 (15)0.0070 (11)0.0073 (12)0.0111 (12)
N40.0219 (14)0.0215 (15)0.0241 (15)0.0037 (12)0.0072 (12)0.0093 (12)
N50.092 (6)0.157 (10)0.279 (15)0.039 (6)0.091 (9)0.164 (11)
C10.0221 (17)0.0165 (17)0.043 (2)−0.0005 (14)0.0027 (16)0.0093 (16)
C20.0188 (15)0.0178 (16)0.0235 (17)0.0024 (13)0.0060 (13)0.0052 (13)
C30.0197 (15)0.0154 (15)0.0249 (17)0.0043 (12)0.0079 (13)0.0072 (13)
C40.0161 (14)0.0188 (16)0.0199 (16)0.0049 (12)0.0065 (12)0.0083 (13)
C50.0180 (15)0.0175 (15)0.0225 (17)0.0071 (12)0.0085 (13)0.0060 (13)
C60.0235 (17)0.0196 (16)0.0293 (19)0.0069 (14)0.0083 (15)0.0118 (15)
C70.0288 (19)0.0268 (19)0.034 (2)0.0139 (16)0.0054 (16)0.0136 (17)
C80.0212 (18)0.027 (2)0.049 (3)0.0110 (15)0.0010 (18)0.0107 (19)
C90.0171 (17)0.032 (2)0.051 (3)0.0076 (15)0.0110 (17)0.018 (2)
C100.0185 (16)0.0196 (16)0.0303 (19)0.0079 (13)0.0081 (14)0.0106 (14)
C110.0161 (14)0.0177 (15)0.0164 (15)0.0046 (12)0.0058 (12)0.0063 (12)
C120.0168 (14)0.0162 (15)0.0204 (16)0.0032 (12)0.0024 (12)0.0064 (13)
C130.0162 (14)0.0163 (15)0.0191 (16)0.0026 (12)0.0029 (12)0.0054 (12)
C140.0168 (14)0.0148 (15)0.0185 (15)0.0026 (12)0.0065 (12)0.0056 (12)
C150.0190 (15)0.0150 (15)0.0228 (17)0.0051 (12)0.0096 (13)0.0073 (13)
C160.0190 (15)0.0151 (15)0.0219 (16)0.0031 (12)0.0021 (13)0.0084 (13)
C170.0238 (18)0.0223 (18)0.041 (2)0.0054 (15)0.0099 (17)0.0075 (17)
C180.0182 (17)0.026 (2)0.045 (3)−0.0001 (15)0.0087 (16)0.0106 (18)
C190.0258 (18)0.0171 (16)0.030 (2)−0.0028 (14)−0.0057 (15)0.0093 (15)
C200.035 (2)0.0154 (16)0.0207 (17)0.0038 (14)0.0030 (15)0.0053 (13)
C210.0280 (18)0.0168 (16)0.0250 (18)0.0057 (14)0.0082 (15)0.0091 (14)
C220.0220 (16)0.0166 (15)0.0258 (18)0.0077 (13)0.0072 (14)0.0091 (14)
C230.0183 (15)0.0208 (16)0.0249 (18)0.0084 (13)0.0058 (13)0.0088 (14)
C240.0221 (17)0.0248 (19)0.038 (2)0.0076 (15)−0.0004 (16)0.0106 (17)
C250.0145 (14)0.0168 (15)0.0158 (15)0.0053 (12)0.0038 (12)0.0043 (12)
C260.0161 (14)0.0136 (14)0.0152 (14)0.0032 (12)0.0047 (12)0.0026 (12)
C270.0296 (19)0.034 (2)0.0245 (19)0.0118 (16)0.0036 (15)0.0172 (16)
C280.0215 (16)0.0263 (18)0.0205 (17)0.0112 (14)0.0078 (13)0.0126 (14)
C290.0200 (16)0.0281 (18)0.0171 (16)0.0079 (14)0.0034 (13)0.0083 (14)
C300.0196 (15)0.0209 (16)0.0175 (16)0.0052 (13)0.0062 (13)0.0069 (13)
C310.0259 (17)0.0203 (16)0.0170 (16)0.0064 (14)0.0052 (13)0.0059 (13)
C320.0245 (18)0.0258 (19)0.0266 (19)0.0032 (15)0.0040 (15)0.0043 (16)
C330.036 (2)0.025 (2)0.032 (2)−0.0025 (17)0.0045 (18)0.0037 (17)
C340.049 (3)0.0201 (19)0.030 (2)0.0033 (17)0.0117 (19)0.0041 (16)
C350.046 (2)0.0225 (19)0.030 (2)0.0138 (17)0.0155 (19)0.0087 (16)
C360.0290 (19)0.0240 (18)0.0257 (19)0.0084 (15)0.0090 (15)0.0096 (15)
C370.0192 (15)0.0211 (16)0.0150 (15)0.0079 (13)0.0063 (12)0.0066 (13)
C380.0230 (16)0.0190 (16)0.0199 (16)0.0084 (13)0.0064 (13)0.0093 (13)
C390.0221 (16)0.0259 (17)0.0151 (15)0.0097 (14)0.0033 (13)0.0105 (13)
C400.0189 (15)0.0195 (16)0.0180 (16)0.0046 (13)0.0046 (13)0.0026 (13)
C410.0191 (16)0.0274 (19)0.0229 (18)0.0055 (14)0.0050 (14)0.0084 (15)
C420.0171 (16)0.034 (2)0.0239 (18)0.0058 (15)0.0012 (14)0.0104 (16)
C430.029 (2)0.038 (2)0.029 (2)0.0138 (18)−0.0002 (17)0.0058 (18)
C440.031 (2)0.046 (3)0.040 (3)0.018 (2)0.0034 (19)0.014 (2)
C450.0204 (17)0.048 (3)0.030 (2)0.0050 (17)−0.0049 (16)0.020 (2)
C460.0191 (17)0.045 (3)0.0239 (19)−0.0032 (17)−0.0005 (15)0.0105 (18)
C470.0198 (16)0.033 (2)0.0257 (19)0.0022 (15)0.0051 (14)0.0090 (16)
C480.0242 (18)0.0262 (19)0.029 (2)−0.0003 (15)0.0034 (15)0.0081 (16)
C490.0259 (18)0.0241 (18)0.029 (2)−0.0012 (15)0.0079 (15)0.0072 (16)
C500.038 (2)0.031 (2)0.039 (2)−0.0032 (18)0.0068 (19)0.0168 (19)
C510.0184 (15)0.0200 (16)0.0199 (16)0.0063 (13)0.0081 (13)0.0067 (13)
C520.0173 (15)0.0233 (17)0.0168 (15)0.0094 (13)0.0048 (12)0.0076 (13)
C530.132 (9)0.093 (7)0.089 (6)0.029 (6)0.055 (6)0.050 (5)
C540.083 (6)0.143 (10)0.176 (12)0.030 (7)0.061 (8)0.124 (10)

Geometric parameters (Å, °)

Hg1—Cl22.3892 (10)C26—N11.359 (4)
Hg1—Cl12.3921 (11)C27—C281.496 (5)
Hg2—Cl42.3847 (12)C27—H27A0.9600
Hg2—Cl32.4420 (11)C27—H27B0.9600
N1—Hg12.337 (3)C27—H27C0.9600
N2—Hg12.331 (3)C28—N31.336 (5)
N3—Hg22.328 (3)C28—C291.399 (6)
N4—Hg22.319 (3)C29—C301.380 (5)
C1—C21.496 (5)C29—H290.9300
C1—H1A0.9600C30—C371.428 (5)
C1—H1B0.9600C30—C311.477 (5)
C1—H1C0.9600C31—C321.399 (5)
C2—N11.328 (5)C31—C361.399 (6)
C2—C31.400 (5)C32—C331.396 (6)
C3—C41.382 (5)C32—H320.9300
C3—H30.9300C33—C341.384 (7)
C4—C111.423 (5)C33—H330.9300
C4—C51.491 (5)C34—C351.396 (7)
C5—C61.391 (5)C34—H340.9300
C5—C101.406 (5)C35—C361.393 (6)
C6—C71.396 (5)C35—H350.9300
C6—H60.9300C36—H360.9300
C7—C81.386 (6)C37—C521.416 (5)
C7—H70.9300C37—C381.431 (5)
C8—C91.373 (7)C38—C391.357 (5)
C8—H80.9300C38—H380.9300
C9—C101.381 (5)C39—C401.435 (5)
C9—H90.9300C39—H390.9300
C10—H100.9300C40—C511.403 (5)
C11—C261.414 (5)C40—C411.434 (5)
C11—C121.430 (5)C41—C481.378 (6)
C12—C131.354 (5)C41—C421.474 (6)
C12—H120.9300C42—C471.398 (6)
C13—C141.433 (5)C42—C431.401 (6)
C13—H130.9300C43—C441.382 (6)
C14—C151.415 (5)C43—H430.9300
C14—C251.416 (4)C44—C451.374 (7)
C15—C221.380 (5)C44—H440.9300
C15—C161.482 (5)C45—C461.392 (7)
C16—C211.388 (5)C45—H450.9300
C16—C171.390 (5)C46—C471.392 (6)
C17—C181.400 (5)C46—H460.9300
C17—H170.9300C47—H470.9300
C18—C191.376 (6)C48—C491.399 (6)
C18—H180.9300C48—H480.9300
C19—C201.386 (6)C49—N41.339 (5)
C19—H190.9300C49—C501.499 (6)
C20—C211.382 (5)C50—H50A0.9600
C20—H200.9300C50—H50B0.9600
C21—H210.9300C50—H50C0.9600
C22—C231.398 (5)C51—N41.351 (5)
C22—H220.9300C51—C521.454 (5)
C23—N21.328 (5)C52—N31.355 (5)
C23—C241.503 (5)C53—C541.430 (15)
C24—H24A0.9600C53—H53C0.9600
C24—H24B0.9600C53—H53B0.9600
C24—H24C0.9600C53—H53A0.9600
C25—N21.364 (4)C54—N51.163 (15)
C25—C261.442 (5)
N2—Hg1—N171.59 (10)N2—C25—C14122.0 (3)
N2—Hg1—Cl2109.36 (8)N2—C25—C26117.9 (3)
N1—Hg1—Cl2122.71 (8)C14—C25—C26120.1 (3)
N2—Hg1—Cl1113.98 (8)N1—C26—C11121.8 (3)
N1—Hg1—Cl1106.46 (8)N1—C26—C25118.5 (3)
Cl2—Hg1—Cl1122.09 (4)C11—C26—C25119.6 (3)
N4—Hg2—N372.04 (11)C28—C27—H27A109.5
N4—Hg2—Cl4118.96 (9)C28—C27—H27B109.5
N3—Hg2—Cl4123.84 (9)H27A—C27—H27B109.5
N4—Hg2—Cl3111.86 (9)C28—C27—H27C109.5
N3—Hg2—Cl3103.17 (8)H27A—C27—H27C109.5
Cl4—Hg2—Cl3118.10 (4)H27B—C27—H27C109.5
C26—N1—Hg1115.7 (2)N3—C28—C29120.8 (3)
C23—N2—C25119.9 (3)N3—C28—C27117.4 (3)
C23—N2—Hg1124.0 (2)C29—C28—C27121.7 (3)
C25—N2—Hg1116.0 (2)C30—C29—C28121.6 (3)
C28—N3—C52119.6 (3)C30—C29—H29119.2
C28—N3—Hg2124.7 (3)C28—C29—H29119.2
C52—N3—Hg2115.6 (2)C29—C30—C37117.7 (3)
C49—N4—C51120.0 (4)C29—C30—C31120.1 (3)
C49—N4—Hg2124.0 (3)C37—C30—C31122.1 (3)
C51—N4—Hg2116.0 (2)C32—C31—C36118.6 (4)
C2—C1—H1A109.5C32—C31—C30120.4 (4)
C2—C1—H1B109.5C36—C31—C30121.0 (3)
H1A—C1—H1B109.5C33—C32—C31120.7 (4)
C2—C1—H1C109.5C33—C32—H32119.7
H1A—C1—H1C109.5C31—C32—H32119.7
H1B—C1—H1C109.5C34—C33—C32120.1 (4)
N1—C2—C3121.0 (3)C34—C33—H33120.0
N1—C2—C1117.6 (3)C32—C33—H33120.0
C3—C2—C1121.4 (3)C33—C34—C35120.1 (4)
C4—C3—C2120.9 (3)C33—C34—H34120.0
C4—C3—H3119.5C35—C34—H34120.0
C2—C3—H3119.5C36—C35—C34119.7 (4)
C3—C4—C11118.2 (3)C36—C35—H35120.1
C3—C4—C5119.8 (3)C34—C35—H35120.1
C11—C4—C5122.0 (3)C35—C36—C31120.9 (4)
C6—C5—C10118.8 (3)C35—C36—H36119.6
C6—C5—C4119.5 (3)C31—C36—H36119.6
C10—C5—C4121.7 (3)C52—C37—C30117.3 (3)
C5—C6—C7120.8 (4)C52—C37—C38119.2 (3)
C5—C6—H6119.6C30—C37—C38123.4 (3)
C7—C6—H6119.6C39—C38—C37120.7 (3)
C8—C7—C6119.2 (4)C39—C38—H38119.6
C8—C7—H7120.4C37—C38—H38119.6
C6—C7—H7120.4C38—C39—C40121.2 (3)
C9—C8—C7120.4 (4)C38—C39—H39119.4
C9—C8—H8119.8C40—C39—H39119.4
C7—C8—H8119.8C51—C40—C41117.7 (3)
C8—C9—C10120.9 (4)C51—C40—C39119.5 (3)
C8—C9—H9119.6C41—C40—C39122.8 (3)
C10—C9—H9119.6C48—C41—C40117.8 (4)
C9—C10—C5119.8 (4)C48—C41—C42120.4 (4)
C9—C10—H10120.1C40—C41—C42121.8 (4)
C5—C10—H10120.1C47—C42—C43118.9 (4)
C26—C11—C4117.7 (3)C47—C42—C41119.8 (4)
C26—C11—C12118.5 (3)C43—C42—C41121.3 (4)
C4—C11—C12123.7 (3)C44—C43—C42120.5 (4)
C13—C12—C11121.6 (3)C44—C43—H43119.8
C13—C12—H12119.2C42—C43—H43119.8
C11—C12—H12119.2C45—C44—C43120.6 (5)
C12—C13—C14121.5 (3)C45—C44—H44119.7
C12—C13—H13119.3C43—C44—H44119.7
C14—C13—H13119.3C44—C45—C46119.7 (4)
C15—C14—C25117.8 (3)C44—C45—H45120.1
C15—C14—C13124.0 (3)C46—C45—H45120.1
C25—C14—C13118.2 (3)C47—C46—C45120.4 (4)
C22—C15—C14118.1 (3)C47—C46—H46119.8
C22—C15—C16118.9 (3)C45—C46—H46119.8
C14—C15—C16123.0 (3)C46—C47—C42119.9 (4)
C21—C16—C17118.5 (3)C46—C47—H47120.0
C21—C16—C15121.4 (3)C42—C47—H47120.0
C17—C16—C15120.0 (3)C41—C48—C49121.3 (4)
C16—C17—C18120.8 (4)C41—C48—H48119.3
C16—C17—H17119.6C49—C48—H48119.3
C18—C17—H17119.6N4—C49—C48120.6 (4)
C19—C18—C17119.5 (4)N4—C49—C50117.9 (4)
C19—C18—H18120.2C48—C49—C50121.4 (4)
C17—C18—H18120.2C49—C50—H50A109.5
C18—C19—C20120.2 (4)C49—C50—H50B109.5
C18—C19—H19119.9H50A—C50—H50B109.5
C20—C19—H19119.9C49—C50—H50C109.5
C21—C20—C19119.9 (4)H50A—C50—H50C109.5
C21—C20—H20120.0H50B—C50—H50C109.5
C19—C20—H20120.0N4—C51—C40122.5 (3)
C20—C21—C16121.0 (4)N4—C51—C52118.3 (3)
C20—C21—H21119.5C40—C51—C52119.2 (3)
C16—C21—H21119.5N3—C52—C37122.6 (3)
C15—C22—C23121.5 (3)N3—C52—C51118.1 (3)
C15—C22—H22119.2C37—C52—C51119.3 (3)
C23—C22—H22119.2C54—C53—H53C109.4
N2—C23—C22120.8 (3)C54—C53—H53B109.5
N2—C23—C24118.0 (3)H53C—C53—H53B109.5
C22—C23—C24121.3 (3)C54—C53—H53A109.5
C23—C24—H24A109.5H53C—C53—H53A109.5
C23—C24—H24B109.5H53B—C53—H53A109.5
H24A—C24—H24B109.5N5—C54—C53170.9 (16)
C23—C24—H24C109.5C2—N1—C26120.3 (3)
H24A—C24—H24C109.5C2—N1—Hg1124.0 (2)
H24B—C24—H24C109.5
N1—C2—C3—C4−0.7 (6)C39—C40—C41—C42−6.1 (6)
C1—C2—C3—C4−179.3 (4)C48—C41—C42—C47−54.9 (6)
C2—C3—C4—C11−1.5 (5)C40—C41—C42—C47126.7 (4)
C2—C3—C4—C5176.9 (3)C48—C41—C42—C43124.6 (5)
C3—C4—C5—C647.8 (5)C40—C41—C42—C43−53.8 (6)
C11—C4—C5—C6−133.8 (4)C47—C42—C43—C441.6 (7)
C3—C4—C5—C10−131.5 (4)C41—C42—C43—C44−177.8 (4)
C11—C4—C5—C1046.9 (5)C42—C43—C44—C45−2.4 (8)
C10—C5—C6—C7−3.7 (6)C43—C44—C45—C461.4 (8)
C4—C5—C6—C7176.9 (4)C44—C45—C46—C470.4 (7)
C5—C6—C7—C81.2 (6)C45—C46—C47—C42−1.1 (6)
C6—C7—C8—C91.9 (7)C43—C42—C47—C460.1 (6)
C7—C8—C9—C10−2.3 (7)C41—C42—C47—C46179.6 (4)
C8—C9—C10—C5−0.3 (7)C40—C41—C48—C491.0 (6)
C6—C5—C10—C93.3 (6)C42—C41—C48—C49−177.4 (4)
C4—C5—C10—C9−177.4 (4)C41—C48—C49—N41.0 (7)
C3—C4—C11—C263.1 (5)C41—C48—C49—C50178.8 (4)
C5—C4—C11—C26−175.3 (3)C41—C40—C51—N42.6 (5)
C3—C4—C11—C12−174.3 (3)C39—C40—C51—N4−175.7 (3)
C5—C4—C11—C127.3 (6)C41—C40—C51—C52−177.0 (3)
C26—C11—C12—C135.9 (5)C39—C40—C51—C524.7 (5)
C4—C11—C12—C13−176.7 (4)C30—C37—C52—N3−4.5 (5)
C11—C12—C13—C140.4 (6)C38—C37—C52—N3172.9 (3)
C12—C13—C14—C15175.3 (4)C30—C37—C52—C51173.3 (3)
C12—C13—C14—C25−5.5 (5)C38—C37—C52—C51−9.3 (5)
C25—C14—C15—C22−0.8 (5)N4—C51—C52—N31.3 (5)
C13—C14—C15—C22178.4 (3)C40—C51—C52—N3−179.0 (3)
C25—C14—C15—C16176.6 (3)N4—C51—C52—C37−176.7 (3)
C13—C14—C15—C16−4.2 (6)C40—C51—C52—C373.0 (5)
C22—C15—C16—C21−57.1 (5)C3—C2—N1—C261.2 (6)
C14—C15—C16—C21125.5 (4)C1—C2—N1—C26179.8 (4)
C22—C15—C16—C17118.7 (4)C3—C2—N1—Hg1−178.3 (3)
C14—C15—C16—C17−58.7 (5)C1—C2—N1—Hg10.2 (5)
C21—C16—C17—C180.9 (6)C11—C26—N1—C20.5 (5)
C15—C16—C17—C18−175.0 (4)C25—C26—N1—C2−177.8 (3)
C16—C17—C18—C19−2.1 (7)C11—C26—N1—Hg1−179.8 (3)
C17—C18—C19—C201.1 (7)C25—C26—N1—Hg11.9 (4)
C18—C19—C20—C211.1 (6)C22—C23—N2—C25−0.7 (6)
C19—C20—C21—C16−2.3 (6)C24—C23—N2—C25−179.4 (3)
C17—C16—C21—C201.3 (6)C22—C23—N2—Hg1−177.2 (3)
C15—C16—C21—C20177.2 (4)C24—C23—N2—Hg14.1 (5)
C14—C15—C22—C230.1 (6)C14—C25—N2—C230.0 (5)
C16—C15—C22—C23−177.4 (4)C26—C25—N2—C23177.3 (3)
C15—C22—C23—N20.7 (6)C14—C25—N2—Hg1176.7 (3)
C15—C22—C23—C24179.4 (4)C26—C25—N2—Hg1−6.0 (4)
C15—C14—C25—N20.8 (5)C29—C28—N3—C524.4 (5)
C13—C14—C25—N2−178.4 (3)C27—C28—N3—C52−178.7 (3)
C15—C14—C25—C26−176.4 (3)C29—C28—N3—Hg2−173.2 (3)
C13—C14—C25—C264.3 (5)C27—C28—N3—Hg23.7 (5)
C4—C11—C26—N1−2.7 (5)C37—C52—N3—C28−1.1 (5)
C12—C11—C26—N1174.9 (3)C51—C52—N3—C28−179.0 (3)
C4—C11—C26—C25175.5 (3)C37—C52—N3—Hg2176.7 (3)
C12—C11—C26—C25−6.9 (5)C51—C52—N3—Hg2−1.2 (4)
N2—C25—C26—N12.8 (5)C48—C49—N4—C51−1.2 (6)
C14—C25—C26—N1−179.8 (3)C50—C49—N4—C51−179.1 (4)
N2—C25—C26—C11−175.5 (3)C48—C49—N4—Hg2178.5 (3)
C14—C25—C26—C111.8 (5)C50—C49—N4—Hg20.7 (6)
N3—C28—C29—C30−1.9 (6)C40—C51—N4—C49−0.6 (6)
C27—C28—C29—C30−178.7 (4)C52—C51—N4—C49179.0 (4)
C28—C29—C30—C37−3.8 (5)C40—C51—N4—Hg2179.6 (3)
C28—C29—C30—C31173.5 (4)C52—C51—N4—Hg2−0.7 (4)
C29—C30—C31—C3241.6 (5)C23—N2—Hg1—N1−178.4 (3)
C37—C30—C31—C32−141.2 (4)C25—N2—Hg1—N15.0 (2)
C29—C30—C31—C36−134.9 (4)C23—N2—Hg1—Cl262.5 (3)
C37—C30—C31—C3642.3 (5)C25—N2—Hg1—Cl2−114.1 (2)
C36—C31—C32—C33−1.2 (6)C23—N2—Hg1—Cl1−78.1 (3)
C30—C31—C32—C33−177.7 (4)C25—N2—Hg1—Cl1105.3 (2)
C31—C32—C33—C340.2 (7)C2—N1—Hg1—N2176.1 (3)
C32—C33—C34—C350.6 (7)C26—N1—Hg1—N2−3.6 (2)
C33—C34—C35—C36−0.3 (7)C2—N1—Hg1—Cl2−82.3 (3)
C34—C35—C36—C31−0.8 (7)C26—N1—Hg1—Cl298.1 (2)
C32—C31—C36—C351.6 (6)C2—N1—Hg1—Cl165.7 (3)
C30—C31—C36—C35178.1 (4)C26—N1—Hg1—Cl1−113.9 (2)
C29—C30—C37—C526.7 (5)C49—N4—Hg2—N3−179.7 (3)
C31—C30—C37—C52−170.5 (3)C51—N4—Hg2—N30.1 (3)
C29—C30—C37—C38−170.5 (3)C49—N4—Hg2—Cl461.0 (3)
C31—C30—C37—C3812.2 (6)C51—N4—Hg2—Cl4−119.2 (3)
C52—C37—C38—C398.0 (5)C49—N4—Hg2—Cl3−82.3 (3)
C30—C37—C38—C39−174.8 (4)C51—N4—Hg2—Cl397.5 (3)
C37—C38—C39—C40−0.2 (6)C28—N3—Hg2—N4178.3 (3)
C38—C39—C40—C51−6.2 (6)C52—N3—Hg2—N40.6 (2)
C38—C39—C40—C41175.6 (4)C28—N3—Hg2—Cl4−68.4 (3)
C51—C40—C41—C48−2.7 (5)C52—N3—Hg2—Cl4113.9 (2)
C39—C40—C41—C48175.5 (4)C28—N3—Hg2—Cl369.3 (3)
C51—C40—C41—C42175.7 (4)C52—N3—Hg2—Cl3−108.5 (2)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2718).

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