(2,9-Dimethyl-4,7-diphenyl-1,10-phen­anthroline-κ2N,N′)bis­(thio­cyanato-κS)mercury(II)

Alizadeh, R.

doi:10.1107/S1600536809023228

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Pages m817-m818

doi:10.1107/S1600536809023228

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(2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline-κ²N,N′)bis(thiocyanato-κS)mercury(II)

Robabeh Alizadeh ^a ^*

^aDamghan University of Basic Sciences, School of Chemistry, Damghan, Iran
^*Correspondence e-mail: robabeh_alizadeh@yahoo.com

(Received 12 June 2009; accepted 16 June 2009; online 24 June 2009)

In the molecule of the title compound, [Hg(NCS)₂(C₂₆H₂₀N₂)], the Hg^II atom is four-coordinated in a distorted tetrahedral configuration by two N atoms from a chelating 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline ligand and by two S atoms from two thiocyanate anions. The ligand ring system is not planar. The dihedral angle between the phenyl rings is 53.20 (3)° . In the crystal structure, π–π contacts between phenanthroline rings [centroid–centroid distance = 3.981 (1) Å] may stabilize the structure.

Related literature

For related structures, see: Ahmadi et al. (2008 ); Alizadeh et al. (2009 ); Hughes et al. (1985 ); Kalateh et al. (2008 ); Khoshtarkib et al. (2009 ); Mahjoub & Morsali (2003 ); Morsali (2006 ); Morsali et al. (2003 , 2004 ); Safari et al. (2009 ); Tadayon Pour et al. (2008 ); Xie et al. (2004 ); Yousefi et al. (2009 ); Yousefi, Rashidi Vahid et al. (2008 ); Yousefi, Tadayon Pour et al. (2008 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

[Hg(NCS)₂(C₂₆H₂₀N₂)]
M_r = 677.21
Orthorhombic, P c a n
a = 7.5907 (3) Å
b = 24.0254 (10) Å
c = 28.5284 (14) Å
V = 5202.7 (4) Å³
Z = 8
Mo Kα radiation
μ = 6.10 mm⁻¹
T = 298 K
0.40 × 0.05 × 0.04 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.711, T_max = 0.789
56419 measured reflections
7051 independent reflections
4018 reflections with I > 2σ(I)
R_int = 0.091

Refinement

R[F² > 2σ(F²)] = 0.093
wR(F²) = 0.199
S = 1.21
7051 reflections
318 parameters
H-atom parameters constrained
Δρ_max = 2.55 e Å⁻³
Δρ_min = −1.43 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Hg1—N2	2.309 (10)
Hg1—N1	2.320 (10)
Hg1—S2	2.443 (3)
Hg1—S1	2.456 (4)

N2—Hg1—N1	71.7 (3)
N2—Hg1—S2	115.6 (2)
N1—Hg1—S2	118.6 (2)
N2—Hg1—S1	119.1 (2)
N1—Hg1—S1	114.7 (3)
S2—Hg1—S1	112.00 (12)

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

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809023228/hk2711sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809023228/hk2711Isup2.hkl

checkCIF report

Comment top

Recently, we reported the synthes and crystal structures of [Zn(phend)Cl₂], (II), (Alizadeh et al., 2009) and [Hg(2,9-dmphen)Br₂], (III), (Khoshtarkib et al., 2009) [where phend is phenanthridine and 2,9-dmphen is 2,9-dimethyl-1,10-phenanthroline]. There are several Hg^II complexes, with formula, [Hg(N—N)X₂], (X=Br, Cl, I and SCN), such as [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], (IIX), (Yousefi, Allahgholi Ghasri 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 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).

In the molecule of the title compound (Fig 1), Hg^II atom is four-coordinated in a distorted tetrahedral configuration by two N atoms from 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline and two S atoms from two thiocyanate anions (Table 1). The bond lengths (Allen et al., 1987) and angles are within normal ranges, and are in accordance with the corresponding values in (XV). Rings A (N1/C2-C4/C11/C26), B (C11-C14/C25/C26) and C (N2/C14/C15/C22/C23/C25) are, of course, planar and the dihedral angles between them are A/B = 5.43 (3), A/C = 6.53 (3) and B/C = 4.07 (3) °. So, the phenanthroline ring system is not planar. The phenyl rings D (C5-C10) and E (C16-C21) are oriented at a dihedral angle of 53.20 (3)°.

In the crystal structure (Fig. 2), the π–π contact between the phenanthroline rings, Cg2—Cg2ⁱ [symmetry code: (i) 1/2 + x, 1/2 - y, z, where Cg2 is centroid of the ring B (C11-C14/C25/C26)] may stabilize the structure, with centroid-centroid distance of 3.981 (1) Å.

Related literature top

For related structures, see: Ahmadi et al. (2008); Alizadeh et al. (2009); Hughes et al. (1985); Kalateh et al. (2008); Khoshtarkib et al. (2009); Mahjoub & Morsali (2003); Morsali (2006); Morsali et al. (2003, 2004); Safari et al. (2009); Tadayon Pour et al. (2008); Xie et al. (2004); Yousefi et al. (2009); Yousefi, Rashidi Vahid et al. (2008); Yousefi, Tadayon Pour et al. (2008). For bond-length data, see: Allen et al. (1987).

Experimental top

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 Hg(SCN)₂ (0.35 g, 1.10 mmol) in methanol (20 ml) and the resulting pale yellow solution was stirred for 20 min at room temperature, and then it was left to evaporate slowly at room temperature. After one week, colorless needle crystals of the title compound were isolated (yield; 0.53 g, 71.1%).

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A partial packing diagram of the title compound.

(2,9-Dimethyl-4,7-diphenyl-1,10-phenanthroline- κ²N,N')bis(thiocyanato-κS)mercury(II) top

Crystal data top

[Hg(NCS)₂(C₂₆H₂₀N₂)]	F(000) = 2624
M_r = 677.21	D_x = 1.729 Mg m⁻³
Orthorhombic, Pcan	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2c	Cell parameters from 1276 reflections
a = 7.5907 (3) Å	θ = 1.7–29.3°
b = 24.0254 (10) Å	µ = 6.10 mm⁻¹
c = 28.5284 (14) Å	T = 298 K
V = 5202.7 (4) Å³	Needle, colorless
Z = 8	0.40 × 0.05 × 0.04 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	7051 independent reflections
Radiation source: fine-focus sealed tube	4018 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.091
ϕ and ω scans	θ_max = 29.3°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −10→10
T_min = 0.711, T_max = 0.789	k = −32→32
56419 measured reflections	l = −38→39

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.093	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.199	H-atom parameters constrained
S = 1.21	w = 1/[σ²(F_o²) + (0.0612P)² + 12.3403P] where P = (F_o² + 2F_c²)/3
7051 reflections	(Δ/σ)_max = 0.007
318 parameters	Δρ_max = 2.55 e Å⁻³
0 restraints	Δρ_min = −1.43 e Å⁻³

Crystal data top

[Hg(NCS)₂(C₂₆H₂₀N₂)]	V = 5202.7 (4) Å³
M_r = 677.21	Z = 8
Orthorhombic, Pcan	Mo Kα radiation
a = 7.5907 (3) Å	µ = 6.10 mm⁻¹
b = 24.0254 (10) Å	T = 298 K
c = 28.5284 (14) Å	0.40 × 0.05 × 0.04 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	7051 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	4018 reflections with I > 2σ(I)
T_min = 0.711, T_max = 0.789	R_int = 0.091
56419 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.093	0 restraints
wR(F²) = 0.199	H-atom parameters constrained
S = 1.21	w = 1/[σ²(F_o²) + (0.0612P)² + 12.3403P] where P = (F_o² + 2F_c²)/3
7051 reflections	Δρ_max = 2.55 e Å⁻³
318 parameters	Δρ_min = −1.43 e Å⁻³

Special details top

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) top

	x	y	z	U_iso*/U_eq
Hg1	0.43243 (6)	0.550529 (15)	0.12578 (2)	0.06252 (17)
S1	0.1392 (5)	0.51033 (16)	0.1124 (2)	0.092 (2)
S2	0.6577 (4)	0.47883 (13)	0.13551 (15)	0.0792 (11)
N1	0.4970 (11)	0.6275 (4)	0.0798 (4)	0.046 (2)
N2	0.4592 (12)	0.6271 (4)	0.1742 (4)	0.050 (2)
N3	−0.089 (2)	0.5979 (7)	0.1294 (11)	0.103 (11)
N4	0.451 (2)	0.3831 (6)	0.1223 (9)	0.110 (8)
C1	0.487 (2)	0.5700 (6)	0.0093 (6)	0.077 (4)
H1A	0.5691	0.5442	0.0230	0.115*
H1B	0.5113	0.5736	−0.0236	0.115*
H1C	0.3694	0.5567	0.0137	0.115*
C2	0.5071 (14)	0.6259 (5)	0.0326 (5)	0.054 (3)
C3	0.5329 (15)	0.6751 (6)	0.0080 (5)	0.059 (3)
H3	0.5317	0.6737	−0.0246	0.071*
C4	0.5594 (12)	0.7250 (4)	0.0287 (4)	0.045 (2)
C5	0.5748 (13)	0.7761 (5)	0.0006 (4)	0.051 (2)
C6	0.6648 (16)	0.7735 (6)	−0.0429 (5)	0.070 (3)
H6	0.7145	0.7403	−0.0531	0.084*
C7	0.677 (2)	0.8214 (8)	−0.0698 (5)	0.092 (5)
H7	0.7444	0.8206	−0.0970	0.110*
C8	0.5951 (19)	0.8693 (7)	−0.0578 (6)	0.084 (5)
H8	0.6002	0.8999	−0.0777	0.101*
C9	0.5032 (19)	0.8728 (7)	−0.0158 (7)	0.086 (5)
H9	0.4500	0.9060	−0.0068	0.103*
C10	0.4923 (14)	0.8254 (5)	0.0126 (5)	0.056 (3)
H10	0.4279	0.8272	0.0403	0.068*
C11	0.5596 (11)	0.7257 (4)	0.0793 (4)	0.042 (2)
C12	0.6003 (11)	0.7739 (4)	0.1072 (4)	0.042 (2)
H12	0.6380	0.8062	0.0923	0.050*
C13	0.5857 (11)	0.7738 (4)	0.1538 (4)	0.045 (2)
H13	0.6155	0.8056	0.1706	0.053*
C14	0.5246 (10)	0.7252 (4)	0.1785 (4)	0.037 (2)
C15	0.4939 (10)	0.7233 (5)	0.2277 (4)	0.041 (2)
C16	0.5052 (12)	0.7738 (5)	0.2579 (5)	0.053 (3)
C17	0.4287 (15)	0.8247 (5)	0.2438 (5)	0.067 (3)
H17	0.3757	0.8279	0.2145	0.080*
C18	0.433 (2)	0.8701 (6)	0.2741 (7)	0.084 (5)
H18	0.3774	0.9031	0.2659	0.101*
C19	0.521 (3)	0.8660 (9)	0.3164 (7)	0.101 (7)
H19	0.5305	0.8973	0.3355	0.121*
C20	0.594 (2)	0.8167 (9)	0.3307 (6)	0.091 (5)
H20	0.6493	0.8142	0.3597	0.109*
C21	0.5848 (15)	0.7709 (7)	0.3017 (4)	0.072 (4)
H21	0.6328	0.7373	0.3117	0.086*
C22	0.4508 (15)	0.6733 (5)	0.2475 (4)	0.053 (3)
H22	0.4337	0.6713	0.2797	0.064*
C23	0.4319 (14)	0.6253 (4)	0.2205 (4)	0.053 (3)
C24	0.388 (2)	0.5713 (6)	0.2421 (6)	0.084 (4)
H24A	0.2707	0.5607	0.2335	0.127*
H24B	0.3963	0.5744	0.2756	0.127*
H24C	0.4697	0.5435	0.2313	0.127*
C25	0.5027 (11)	0.6756 (4)	0.1536 (4)	0.037 (2)
C26	0.5208 (11)	0.6759 (5)	0.1032 (4)	0.037 (2)
C27	0.011 (2)	0.5638 (6)	0.1219 (9)	0.098 (6)
C28	0.5282 (17)	0.4244 (5)	0.1283 (7)	0.077 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Hg1	0.0714 (3)	0.03722 (19)	0.0789 (3)	−0.00113 (17)	0.0051 (3)	0.0002 (2)
S1	0.079 (2)	0.0619 (19)	0.126 (7)	−0.0174 (17)	−0.003 (3)	−0.026 (3)
S2	0.0708 (19)	0.0547 (15)	0.112 (3)	0.0096 (13)	0.006 (2)	0.0001 (18)
N1	0.062 (5)	0.038 (5)	0.039 (6)	0.002 (3)	−0.007 (4)	−0.004 (4)
N2	0.055 (5)	0.036 (4)	0.059 (7)	0.006 (4)	0.012 (4)	0.008 (4)
N3	0.093 (10)	0.077 (9)	0.12 (3)	−0.007 (7)	−0.007 (14)	−0.034 (15)
N4	0.116 (11)	0.066 (8)	0.13 (2)	−0.012 (7)	0.009 (14)	−0.015 (12)
C1	0.125 (11)	0.048 (7)	0.057 (9)	−0.001 (6)	−0.014 (7)	−0.013 (6)
C2	0.056 (6)	0.056 (7)	0.049 (8)	0.007 (4)	−0.006 (5)	−0.010 (6)
C3	0.061 (7)	0.080 (9)	0.037 (7)	0.001 (5)	−0.023 (5)	−0.004 (6)
C4	0.028 (4)	0.062 (6)	0.045 (6)	−0.004 (4)	−0.014 (4)	0.002 (4)
C5	0.047 (5)	0.060 (6)	0.046 (6)	−0.015 (5)	−0.018 (5)	0.012 (5)
C6	0.069 (8)	0.095 (9)	0.047 (8)	0.000 (7)	−0.010 (6)	0.020 (6)
C7	0.075 (9)	0.142 (15)	0.058 (9)	−0.016 (10)	−0.010 (7)	0.036 (10)
C8	0.084 (10)	0.099 (11)	0.069 (10)	−0.026 (8)	−0.017 (8)	0.045 (9)
C9	0.090 (10)	0.071 (10)	0.096 (14)	−0.011 (6)	−0.021 (8)	0.038 (10)
C10	0.057 (6)	0.061 (7)	0.051 (8)	−0.012 (5)	−0.013 (5)	0.017 (6)
C11	0.026 (4)	0.044 (4)	0.055 (6)	−0.004 (4)	−0.008 (4)	−0.001 (4)
C12	0.035 (5)	0.043 (4)	0.047 (6)	−0.003 (3)	−0.004 (4)	0.007 (4)
C13	0.042 (5)	0.048 (5)	0.044 (6)	−0.009 (4)	−0.004 (4)	−0.004 (4)
C14	0.022 (4)	0.054 (6)	0.034 (6)	0.001 (3)	0.004 (3)	−0.001 (4)
C15	0.027 (4)	0.054 (6)	0.040 (6)	0.004 (3)	0.004 (3)	−0.004 (5)
C16	0.042 (5)	0.066 (8)	0.050 (8)	−0.007 (4)	0.014 (4)	−0.008 (6)
C17	0.054 (6)	0.061 (7)	0.085 (10)	−0.005 (5)	0.025 (7)	−0.017 (6)
C18	0.085 (9)	0.072 (9)	0.097 (13)	0.004 (7)	0.034 (9)	−0.025 (8)
C19	0.128 (14)	0.098 (13)	0.077 (13)	−0.047 (10)	0.045 (10)	−0.047 (11)
C20	0.096 (11)	0.127 (15)	0.051 (9)	−0.026 (10)	0.009 (7)	−0.037 (9)
C21	0.062 (7)	0.115 (11)	0.038 (7)	−0.011 (7)	0.002 (6)	−0.010 (6)
C22	0.063 (6)	0.055 (6)	0.041 (6)	0.003 (5)	0.017 (5)	0.007 (5)
C23	0.052 (6)	0.048 (5)	0.059 (8)	0.005 (5)	0.021 (6)	0.010 (5)
C24	0.115 (11)	0.063 (7)	0.075 (10)	0.005 (7)	0.030 (8)	0.029 (7)
C25	0.040 (5)	0.034 (5)	0.036 (7)	0.006 (3)	−0.003 (4)	0.000 (4)
C26	0.032 (4)	0.047 (6)	0.031 (5)	−0.004 (3)	−0.008 (3)	−0.005 (5)
C27	0.076 (8)	0.055 (7)	0.16 (2)	−0.011 (6)	−0.007 (10)	0.037 (13)
C28	0.084 (8)	0.055 (6)	0.093 (11)	0.002 (6)	0.044 (8)	0.020 (8)

Geometric parameters (Å, º) top

Hg1—N2	2.309 (10)	C13—H13	0.9300
Hg1—N1	2.320 (10)	C14—C25	1.397 (15)
Hg1—S2	2.443 (3)	C14—C15	1.425 (15)
Hg1—S1	2.456 (4)	C15—C22	1.366 (16)
C1—C2	1.505 (18)	C15—C16	1.491 (17)
C1—H1A	0.9600	C16—C21	1.390 (18)
C1—H1B	0.9600	C16—C17	1.412 (18)
C1—H1C	0.9600	C17—C18	1.391 (19)
C2—N1	1.349 (16)	C17—H17	0.9300
C2—C3	1.389 (19)	C18—C19	1.38 (3)
C3—C4	1.351 (17)	C18—H18	0.9300
C3—H3	0.9300	C19—C20	1.37 (3)
C4—C11	1.445 (15)	C19—H19	0.9300
C4—C5	1.470 (14)	C20—C21	1.38 (2)
C5—C10	1.385 (18)	C20—H20	0.9300
C5—C6	1.416 (18)	C21—H21	0.9300
C6—C7	1.387 (19)	C22—C23	1.395 (16)
C6—H6	0.9300	C22—H22	0.9300
C7—C8	1.35 (2)	C23—N2	1.337 (16)
C7—H7	0.9300	C23—C24	1.476 (15)
C8—C9	1.39 (3)	C24—H24A	0.9600
C8—H8	0.9300	C24—H24B	0.9600
C9—C10	1.401 (19)	C24—H24C	0.9600
C9—H9	0.9300	C25—N2	1.346 (13)
C10—H10	0.9300	C25—C26	1.446 (14)
C11—C26	1.408 (14)	C26—N1	1.353 (14)
C11—C12	1.438 (13)	C27—N3	1.14 (2)
C12—C13	1.334 (15)	C27—S1	1.635 (18)
C12—H12	0.9300	C28—N4	1.17 (2)
C13—C14	1.441 (14)	C28—S2	1.648 (15)

N2—Hg1—N1	71.7 (3)	C13—C12—C11	122.2 (9)
N2—Hg1—S2	115.6 (2)	C13—C12—H12	118.9
N1—Hg1—S2	118.6 (2)	C11—C12—H12	118.9
N2—Hg1—S1	119.1 (2)	C12—C13—C14	121.0 (9)
N1—Hg1—S1	114.7 (3)	C12—C13—H13	119.5
S2—Hg1—S1	112.00 (12)	C14—C13—H13	119.5
C27—S1—Hg1	101.8 (5)	C25—C14—C15	116.9 (10)
C28—S2—Hg1	97.3 (5)	C25—C14—C13	118.9 (10)
C2—N1—C26	120.6 (11)	C15—C14—C13	124.1 (10)
C2—N1—Hg1	123.7 (8)	C22—C15—C14	118.4 (10)
C26—N1—Hg1	115.7 (8)	C22—C15—C16	119.4 (11)
C23—N2—C25	119.7 (10)	C14—C15—C16	122.2 (11)
C23—N2—Hg1	123.5 (7)	C21—C16—C17	118.6 (13)
C25—N2—Hg1	116.7 (8)	C21—C16—C15	120.2 (12)
C2—C1—H1A	109.5	C17—C16—C15	121.2 (12)
C2—C1—H1B	109.5	C18—C17—C16	119.4 (15)
H1A—C1—H1B	109.5	C18—C17—H17	120.3
C2—C1—H1C	109.5	C16—C17—H17	120.3
H1A—C1—H1C	109.5	C19—C18—C17	120.0 (16)
H1B—C1—H1C	109.5	C19—C18—H18	120.0
N1—C2—C3	119.2 (12)	C17—C18—H18	120.0
N1—C2—C1	117.3 (13)	C20—C19—C18	121.0 (15)
C3—C2—C1	123.4 (13)	C20—C19—H19	119.5
C4—C3—C2	123.8 (12)	C18—C19—H19	119.5
C4—C3—H3	118.1	C19—C20—C21	119.6 (16)
C2—C3—H3	118.1	C19—C20—H20	120.2
C3—C4—C11	116.6 (10)	C21—C20—H20	120.2
C3—C4—C5	120.9 (11)	C20—C21—C16	121.4 (15)
C11—C4—C5	122.4 (9)	C20—C21—H21	119.3
C10—C5—C6	118.3 (11)	C16—C21—H21	119.3
C10—C5—C4	122.8 (11)	C15—C22—C23	121.5 (11)
C6—C5—C4	118.7 (11)	C15—C22—H22	119.3
C7—C6—C5	118.7 (14)	C23—C22—H22	119.3
C7—C6—H6	120.6	N2—C23—C22	120.3 (10)
C5—C6—H6	120.6	N2—C23—C24	118.4 (11)
C8—C7—C6	122.3 (15)	C22—C23—C24	121.3 (12)
C8—C7—H7	118.8	C23—C24—H24A	109.5
C6—C7—H7	118.8	C23—C24—H24B	109.5
C7—C8—C9	120.1 (14)	H24A—C24—H24B	109.5
C7—C8—H8	120.0	C23—C24—H24C	109.5
C9—C8—H8	120.0	H24A—C24—H24C	109.5
C8—C9—C10	118.7 (17)	H24B—C24—H24C	109.5
C8—C9—H9	120.6	N2—C25—C14	123.1 (11)
C10—C9—H9	120.6	N2—C25—C26	117.5 (11)
C5—C10—C9	121.7 (14)	C14—C25—C26	119.3 (11)
C5—C10—H10	119.2	N1—C26—C11	121.4 (11)
C9—C10—H10	119.2	N1—C26—C25	118.3 (11)
C26—C11—C12	117.5 (10)	C11—C26—C25	120.3 (11)
C26—C11—C4	118.2 (9)	N3—C27—S1	174.3 (16)
C12—C11—C4	124.2 (9)	N4—C28—S2	173.6 (13)

N1—C2—C3—C4	4.2 (17)	C13—C14—C25—N2	174.8 (8)
C1—C2—C3—C4	−176.6 (12)	C15—C14—C25—C26	176.0 (8)
C2—C3—C4—C11	−0.2 (16)	C13—C14—C25—C26	−7.5 (12)
C2—C3—C4—C5	−176.2 (10)	C12—C11—C26—N1	−173.9 (8)
C3—C4—C5—C10	136.4 (12)	C4—C11—C26—N1	5.0 (13)
C11—C4—C5—C10	−39.3 (14)	C12—C11—C26—C25	7.1 (12)
C3—C4—C5—C6	−37.8 (14)	C4—C11—C26—C25	−174.1 (8)
C11—C4—C5—C6	146.5 (10)	N2—C25—C26—N1	−1.4 (13)
C10—C5—C6—C7	4.6 (16)	C14—C25—C26—N1	−179.3 (8)
C4—C5—C6—C7	179.1 (11)	N2—C25—C26—C11	177.7 (8)
C5—C6—C7—C8	−5 (2)	C14—C25—C26—C11	−0.2 (13)
C6—C7—C8—C9	4 (2)	C3—C2—N1—C26	−3.5 (15)
C7—C8—C9—C10	−2 (2)	C1—C2—N1—C26	177.2 (10)
C6—C5—C10—C9	−3.1 (16)	C3—C2—N1—Hg1	174.9 (7)
C4—C5—C10—C9	−177.3 (11)	C1—C2—N1—Hg1	−4.4 (13)
C8—C9—C10—C5	2 (2)	C11—C26—N1—C2	−1.1 (14)
C3—C4—C11—C26	−4.2 (13)	C25—C26—N1—C2	178.0 (9)
C5—C4—C11—C26	171.7 (8)	C11—C26—N1—Hg1	−179.6 (6)
C3—C4—C11—C12	174.6 (9)	C25—C26—N1—Hg1	−0.6 (10)
C5—C4—C11—C12	−9.6 (14)	N2—Hg1—N1—C2	−177.1 (9)
C26—C11—C12—C13	−6.5 (13)	S2—Hg1—N1—C2	73.2 (8)
C4—C11—C12—C13	174.7 (9)	S1—Hg1—N1—C2	−62.8 (8)
C11—C12—C13—C14	−1.2 (14)	N2—Hg1—N1—C26	1.4 (6)
C12—C13—C14—C25	8.4 (13)	S2—Hg1—N1—C26	−108.3 (6)
C12—C13—C14—C15	−175.4 (9)	S1—Hg1—N1—C26	115.6 (6)
C25—C14—C15—C22	2.0 (12)	C22—C23—N2—C25	−1.0 (16)
C13—C14—C15—C22	−174.3 (9)	C24—C23—N2—C25	−178.7 (10)
C25—C14—C15—C16	−177.3 (8)	C22—C23—N2—Hg1	179.9 (8)
C13—C14—C15—C16	6.4 (13)	C24—C23—N2—Hg1	2.2 (15)
C22—C15—C16—C21	42.1 (14)	C14—C25—N2—C23	1.3 (14)
C14—C15—C16—C21	−138.7 (11)	C26—C25—N2—C23	−176.5 (9)
C22—C15—C16—C17	−134.9 (11)	C14—C25—N2—Hg1	−179.6 (6)
C14—C15—C16—C17	44.4 (13)	C26—C25—N2—Hg1	2.7 (11)
C21—C16—C17—C18	−0.7 (16)	N1—Hg1—N2—C23	177.0 (9)
C15—C16—C17—C18	176.3 (10)	S2—Hg1—N2—C23	−69.4 (9)
C16—C17—C18—C19	3.7 (19)	S1—Hg1—N2—C23	68.4 (9)
C17—C18—C19—C20	−4 (2)	N1—Hg1—N2—C25	−2.1 (6)
C18—C19—C20—C21	2 (2)	S2—Hg1—N2—C25	111.4 (7)
C19—C20—C21—C16	1 (2)	S1—Hg1—N2—C25	−110.7 (7)
C17—C16—C21—C20	−1.7 (17)	N2—Hg1—S1—C27	25.5 (10)
C15—C16—C21—C20	−178.7 (11)	N1—Hg1—S1—C27	−56.4 (10)
C14—C15—C22—C23	−1.8 (15)	S2—Hg1—S1—C27	164.8 (9)
C16—C15—C22—C23	177.5 (10)	N2—Hg1—S2—C28	141.9 (7)
C15—C22—C23—N2	1.3 (17)	N1—Hg1—S2—C28	−135.9 (7)
C15—C22—C23—C24	178.9 (11)	S1—Hg1—S2—C28	1.1 (7)
C15—C14—C25—N2	−1.7 (12)

Experimental details

Crystal data
Chemical formula	[Hg(NCS)₂(C₂₆H₂₀N₂)]
M_r	677.21
Crystal system, space group	Orthorhombic, Pcan
Temperature (K)	298
a, b, c (Å)	7.5907 (3), 24.0254 (10), 28.5284 (14)
V (Å³)	5202.7 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	6.10
Crystal size (mm)	0.40 × 0.05 × 0.04

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.711, 0.789
No. of measured, independent and observed [I > 2σ(I)] reflections	56419, 7051, 4018
R_int	0.091
(sin θ/λ)_max (Å⁻¹)	0.688

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.093, 0.199, 1.21
No. of reflections	7051
No. of parameters	318
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.0612P)² + 12.3403P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	2.55, −1.43

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXTL (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top

Hg1—N2	2.309 (10)	Hg1—S2	2.443 (3)
Hg1—N1	2.320 (10)	Hg1—S1	2.456 (4)

N2—Hg1—N1	71.7 (3)	N2—Hg1—S1	119.1 (2)
N2—Hg1—S2	115.6 (2)	N1—Hg1—S1	114.7 (3)
N1—Hg1—S2	118.6 (2)	S2—Hg1—S1	112.00 (12)

Acknowledgements

We are grateful to the Damghan University of Basic Sciences for financial support.

References

Ahmadi, R., Ebadi, A., Kalateh, K., Norouzi, A. & Amani, V. (2008). Acta Cryst. E64, m1407. Web of Science CSD CrossRef IUCr Journals Google Scholar
Alizadeh, R., Heidari, A., Ahmadi, R. & Amani, V. (2009). Acta Cryst. E65, m483–m484. Web of Science CSD CrossRef IUCr Journals Google Scholar
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (1998). SMART, SAINT and SADABS . Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Hughes, C. M., Favas, M. C., Skelton, B. W. & White, A. H. (1985). Aust. J. Chem. 38, 1521–1527. CSD CrossRef CAS Google Scholar
Kalateh, K., Norouzi, A., Ebadi, A., Ahmadi, R. & Amani, V. (2008). Acta Cryst. E64, m1583–m1584. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Khoshtarkib, Z., Ebadi, A., Alizadeh, R., Ahmadi, R. & Amani, V. (2009). Acta Cryst. E65, m739–m740. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Mahjoub, A. R. & Morsali, A. (2003). J. Coord. Chem. 56, 779–785. Web of Science CSD CrossRef CAS Google Scholar
Morsali, A. (2006). J. Coord. Chem. 59, 1015–1024. Web of Science CSD CrossRef CAS Google Scholar
Morsali, A., Mahjoub, A. R. & Ramazani, A. (2004). J. Coord. Chem. 57, 347–352. Web of Science CSD CrossRef CAS Google Scholar
Morsali, A., Payheghader, M., Poorheravi, M. R. & Jamali, F. (2003). Z. Anorg. Allg. Chem. 629, 1627–1631. Web of Science CSD CrossRef CAS Google Scholar
Safari, N., Amani, V., Abedi, A., Notash, B. & Ng, S. W. (2009). Acta Cryst. E65, m372. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tadayon Pour, N., Ebadi, A., Abedi, A., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1305. Web of Science CSD CrossRef IUCr Journals Google Scholar
Xie, Y., Ni, J., Jiang, H. & Liu, Q. (2004). J. Mol. Struct. 687, 73–78. Web of Science CSD CrossRef CAS Google Scholar
Yousefi, M., Allahgholi Ghasri, M. R., Heidari, A. & Amani, V. (2009). Acta Cryst. E65, m9–m10. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yousefi, M., Rashidi Vahid, R., Amani, V., Arab Chamjangali, M. & Khavasi, H. R. (2008). Acta Cryst. E64, m1339–m1340. Web of Science CSD CrossRef IUCr Journals Google Scholar
Yousefi, M., Tadayon Pour, N., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1259. Web of Science CSD CrossRef IUCr Journals Google Scholar

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