(4,7-Diphenyl-1,10-phenanthroline-κ2N,N′)diiodidomercury(II)

Yousefi, M.; Rashidi Vahid, R.; Amani, V.; Arab Chamjangali, M.; Khavasi, H.R.

doi:10.1107/S160053680803081X

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 10| October 2008| Pages m1339-m1340

doi:10.1107/S160053680803081X

Open

access

(4,7-Diphenyl-1,10-phenanthroline-κ²N,N′)diiodidomercury(II)

Mohammad Yousefi,^a Rabin Rashidi Vahid,^a Vahid Amani,^a ^* Mansour Arab Chamjangali ^b and Hamid Reza Khavasi ^c

^aIslamic Azad University, Shahr-e-Rey Branch, Tehran, Iran, ^bDepartment of Chemistry, Shahrood University of Technology, Shahrood, Iran, and ^cDepartment of Chemistry, Shahid Beheshti University, Tehran 1983963113, Iran
^*Correspondence e-mail: v_amani2002@yahoo.com

(Received 23 September 2008; accepted 24 September 2008; online 27 September 2008)

In the molecule of the title compound, [HgI₂(C₂₄H₁₆N₂)], the Hg^II atom is four-coordinated in a distorted tetrahedral configuration by two N atoms from the bidentate 4,7-diphenyl-1,10-phenanthroline and two iodide ligands. There is a π–π contact between the pyridine and phenyl rings [centroid-to-centroid distance = 4.2387 (4) Å].

Related literature

For related literature, see: Ahmadi, Amani et al. (2008 ); Ahmadi, Kalateh, Ebadi et al. (2008 ); Ahmadi, Kalateh, Abedi et al. (2008 ); Ahmadi, Khalighi et al. (2008 ); Khalighi et al. (2008 ); Khavasi et al. (2008 ); Tadayon Pour et al. (2008 ); Yousefi, Khalighi et al. (2008 ). For related structures, see: Chen et al. (2006 ); Freire et al. (1999 ); Htoon & Ladd (1976 ); Yousefi, Tadayon Pour et al. (2008 ).

Experimental

Crystal data

[HgI₂(C₂₄H₁₆N₂)]
M_r = 786.78
Monoclinic, P 2₁ /n
a = 16.673 (3) Å
b = 8.8964 (18) Å
c = 16.823 (3) Å
β = 109.26 (3)°
V = 2355.7 (9) Å³
Z = 4
Mo Kα radiation
μ = 9.17 mm⁻¹
T = 298 (2) K
0.50 × 0.48 × 0.28 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: numerical shape of crystal determined optically (X-SHAPE and X-RED; Stoe & Cie, 2005 )T_min = 0.016, T_max = 0.080
19129 measured reflections
6340 independent reflections
5356 reflections with I > 2σ(I)
R_int = 0.094

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.183
S = 1.23
6340 reflections
263 parameters
H-atom parameters constrained
Δρ_max = 1.49 e Å⁻³
Δρ_min = −1.10 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

I1—Hg1	2.6441 (8)
I2—Hg1	2.6555 (9)
N1—Hg1	2.425 (7)
N2—Hg1	2.399 (7)

N2—Hg1—N1	69.4 (2)
N2—Hg1—I1	104.08 (17)
N1—Hg1—I1	110.65 (19)
N2—Hg1—I2	107.53 (17)
N1—Hg1—I2	103.11 (19)
I1—Hg1—I2	139.97 (3)

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/S160053680803081X/hk2540sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680803081X/hk2540Isup2.hkl

checkCIF report

Comment top

Recently, we reported the syntheses and crystal structures of [Zn(5,5'-dmbpy)Cl₂], (II), (Khalighi et al., 2008), [Zn(6-mbpy)Cl₂], (III), (Ahmadi, Kalateh, Abedi et al., 2008), [Cd(5,5'-dmbpy)(µ-Cl)₂]_n, (IV), (Ahmadi, Khalighi et al., 2008), [Hg(5,5'-dmbpy)I₂], (V), (Tadayon Pour et al., 2008), [In(4,4'-dmbpy)Cl₃(DMSO)], (VI), (Ahmadi, Kalateh, Ebadi et al., 2008), [Cu(5,5'-dcbpy)(en)(H₂O)₂].2.5H₂O, (VII), (Yousefi, Khalighi et al., 2008), [Au(dmphen)Cl₂][AuCl₄], (VIII), (Ahmadi, Amani et al., 2008), and {[HgCl(dm4bt)]₂(µ-Cl)₂}, (IX), (Khavasi et al., 2008). [where 5,5'-dmbpy is 5,5'-dimethyl-2,2'-bipyridine, 6-mbpy is 6-methyl-2,2'-bipyridine, 4,4'-dmbpy is 4,4'-dimethyl-2,2'-bi- pyridine, DMSO is dimethyl sulfoxide, 5,5'-dcbpy is 2,2'-bipyridine-5,5'-di- carboxylate, en is ethylenediamine, dmphen is 4,7-diphenyl-1,10- phenanthroline and dm4bt is 2,2'-dimethyl-4,4'-bithiazole]. There are several Hg^II complexes, with formula, [HgI₂(N—N)], such as [HgI₂(bipy)], (X), [HgI₂(phen)], (XI) and [HgI₂(2,9-dmphen)], (XII), (Freire et al., 1999), [HgI₂(bipy)][HgI₂], (XIII), (Chen et al., 2006), [HgI₂(4,4'-dmbpy)], (XIV), (Yousefi, Tadayon Pour et al., 2008) and [HgI₂(TMDA)], (XV), (Htoon & Ladd, 1976) [where bipy is 2,2'-bipyridine, phen is 1,10-phenanthroline, dmphen is 2,9-dimethyl-1,10-phenanthroline and TMDA is tetramethylethylenediamine] 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 title compound, (Fig. 1), the Hg^II atom is four-coordinated in a distorted tetrahedral configuration by two N atoms from 4,7-diphenyl-1,10-phenanthroline and two I atoms. The Hg—I and Hg—N bond lengths and angles (Table 1) are within normal ranges, as in (X), (XI) and (XIV).

In the crystal structure, the π–π contact (Fig. 2) between the pyridine and phenyl rings, Cg3···Cg4ⁱ [symmetry code: (i) 3/2 - x, -1/2 + y, 1/2 - z, where Cg3 and Cg4 are centroids of the rings (N1/C1–C3/C10/C24) and (C4–C9), respectively] may stabilize the structure, with centroid–centroid distance of 4.2387 (4) Å.

Related literature top

For related literature, see: Ahmadi, Amani et al. (2008); Ahmadi, Kalateh, Ebadi et al. (2008); Ahmadi, Kalateh, Abedi et al. (2008); Ahmadi, Khalighi et al. (2008); Chen et al. (2006); Freire et al. (1999); Htoon & Ladd (1976); Khalighi et al. (2008); Khavasi et al. (2008); Tadayon Pour et al. (2008); Yousefi, Khalighi et al. (2008); Yousefi, Tadayon Pour et al. (2008). [It would be much more useful to readers if the "Related literature" section had some kind of simple sub-division, so that, instead of just "For related literature, see···" it said, for example, "For general background, see···. For related structures, see···." etc. Please revise this section as indicated.]

Experimental top

For the preparation of the title compound, a solution of 4,7-diphenyl-1,10-phenanthroline (0.36 g, 1.10 mmol) in acetonitrile (20 ml) was added to a solution of HgI₂ (0.50 g, 1.10 mmol) in methanol (20 ml) and the resulting colorless solution was stirred for 20 min at 313 K. This solution was left to evaporate slowly at room temperature. After one week, colorless block crystals of the title compound were isolated (yield; 0.62 g, 71.6%).

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 40% probability level.
	Fig. 2. A partial packing diagram of the title compound.

(4,7-Diphenyl-1,10-phenanthroline-κ²N,N')diiodidomercury(II) top

Crystal data top

[HgI₂(C₂₄H₁₆N₂)]	F(000) = 1440
M_r = 786.78	D_x = 2.218 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2356 reflections
a = 16.673 (3) Å	θ = 2.1–29.3°
b = 8.8964 (18) Å	µ = 9.17 mm⁻¹
c = 16.823 (3) Å	T = 298 K
β = 109.26 (3)°	Block, colourless
V = 2355.7 (9) Å³	0.50 × 0.48 × 0.28 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	6340 independent reflections
Radiation source: fine-focus sealed tube	5356 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.094
ϕ and ω scans	θ_max = 29.3°, θ_min = 2.1°
Absorption correction: numerical shape of crystal determined optically	h = −22→19
T_min = 0.016, T_max = 0.080	k = −12→12
19129 measured reflections	l = −22→23

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.067	H-atom parameters constrained
wR(F²) = 0.183	w = 1/[σ²(F_o²) + (0.085P)² + 4.523P] where P = (F_o² + 2F_c²)/3
S = 1.23	(Δ/σ)_max = 0.009
6340 reflections	Δρ_max = 1.49 e Å⁻³
263 parameters	Δρ_min = −1.11 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0086 (6)

Crystal data top

[HgI₂(C₂₄H₁₆N₂)]	V = 2355.7 (9) Å³
M_r = 786.78	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 16.673 (3) Å	µ = 9.17 mm⁻¹
b = 8.8964 (18) Å	T = 298 K
c = 16.823 (3) Å	0.50 × 0.48 × 0.28 mm
β = 109.26 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	6340 independent reflections
Absorption correction: numerical shape of crystal determined optically	5356 reflections with I > 2σ(I)
T_min = 0.016, T_max = 0.080	R_int = 0.094
19129 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	0 restraints
wR(F²) = 0.183	H-atom parameters constrained
S = 1.23	Δρ_max = 1.49 e Å⁻³
6340 reflections	Δρ_min = −1.11 e Å⁻³
263 parameters

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	0.35746 (2)	0.27882 (4)	0.10505 (2)	0.05561 (16)
I1	0.29465 (5)	0.55290 (7)	0.06892 (4)	0.0694 (2)
I2	0.32177 (5)	−0.00283 (7)	0.05316 (5)	0.0736 (2)
N1	0.5115 (5)	0.2845 (9)	0.1529 (4)	0.0545 (17)
N2	0.4136 (4)	0.2750 (8)	0.2559 (5)	0.0495 (14)
C1	0.5583 (7)	0.2946 (13)	0.1039 (6)	0.065 (2)
H1	0.5314	0.3098	0.0466	0.078*
C2	0.6448 (7)	0.2837 (13)	0.1335 (6)	0.068 (3)
H2	0.6749	0.2930	0.0960	0.081*
C3	0.6884 (6)	0.2594 (10)	0.2172 (6)	0.0524 (18)
C4	0.7831 (6)	0.2515 (11)	0.2502 (7)	0.0550 (19)
C5	0.8260 (8)	0.1623 (13)	0.2086 (9)	0.076 (3)
H5	0.7963	0.1118	0.1592	0.091*
C6	0.9151 (9)	0.1506 (14)	0.2430 (12)	0.101 (5)
H6	0.9442	0.0869	0.2182	0.122*
C7	0.9601 (9)	0.2342 (18)	0.3143 (12)	0.093 (4)
H7	1.0190	0.2274	0.3362	0.112*
C8	0.9178 (7)	0.3244 (19)	0.3510 (9)	0.086 (3)
H8	0.9477	0.3815	0.3976	0.103*
C9	0.8304 (6)	0.3327 (15)	0.3199 (7)	0.068 (2)
H9	0.8024	0.3948	0.3467	0.082*
C10	0.6399 (5)	0.2429 (10)	0.2719 (5)	0.0487 (16)
C11	0.6750 (5)	0.2082 (11)	0.3592 (6)	0.0545 (19)
H11	0.7324	0.1843	0.3816	0.065*
C12	0.6274 (5)	0.2090 (11)	0.4100 (5)	0.0534 (19)
H12	0.6527	0.1855	0.4667	0.064*
C13	0.5399 (5)	0.2448 (8)	0.3793 (5)	0.0411 (14)
C14	0.4883 (5)	0.2524 (9)	0.4320 (5)	0.0456 (15)
C15	0.5272 (6)	0.2456 (9)	0.5252 (5)	0.0478 (16)
C16	0.5965 (6)	0.3362 (12)	0.5672 (5)	0.059 (2)
H16	0.6176	0.4041	0.5370	0.071*
C17	0.6343 (7)	0.3255 (15)	0.6545 (6)	0.071 (3)
H17	0.6798	0.3875	0.6824	0.085*
C18	0.6042 (9)	0.2228 (14)	0.6993 (7)	0.078 (3)
H18	0.6300	0.2140	0.7573	0.094*
C19	0.5350 (9)	0.1323 (12)	0.6573 (7)	0.078 (3)
H19	0.5150	0.0622	0.6873	0.093*
C20	0.4958 (8)	0.1460 (11)	0.5713 (6)	0.062 (2)
H20	0.4482	0.0881	0.5441	0.075*
C21	0.4019 (6)	0.2684 (11)	0.3937 (6)	0.058 (2)
H21	0.3664	0.2743	0.4261	0.069*
C22	0.3682 (5)	0.2756 (11)	0.3070 (6)	0.058 (2)
H22	0.3094	0.2814	0.2830	0.070*
C23	0.5005 (5)	0.2597 (8)	0.2918 (5)	0.0420 (14)
C24	0.5506 (5)	0.2610 (9)	0.2361 (5)	0.0463 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Hg1	0.0541 (2)	0.0529 (2)	0.0461 (2)	0.00215 (13)	−0.00194 (13)	0.00031 (12)
I1	0.0728 (4)	0.0484 (3)	0.0684 (4)	0.0027 (3)	−0.0018 (3)	−0.0002 (3)
I2	0.0846 (5)	0.0496 (3)	0.0714 (4)	0.0056 (3)	0.0051 (3)	−0.0066 (3)
N1	0.049 (3)	0.072 (5)	0.036 (3)	−0.006 (3)	0.006 (3)	−0.002 (3)
N2	0.041 (3)	0.054 (4)	0.047 (3)	0.001 (3)	0.006 (3)	0.001 (3)
C1	0.071 (6)	0.084 (7)	0.037 (4)	−0.001 (5)	0.012 (4)	0.006 (4)
C2	0.066 (6)	0.093 (8)	0.051 (5)	−0.011 (5)	0.028 (4)	−0.006 (5)
C3	0.052 (4)	0.057 (4)	0.052 (4)	−0.005 (4)	0.022 (4)	−0.006 (4)
C4	0.051 (4)	0.055 (4)	0.066 (5)	0.000 (3)	0.029 (4)	0.000 (4)
C5	0.080 (7)	0.059 (5)	0.104 (8)	−0.012 (5)	0.051 (6)	−0.017 (6)
C6	0.086 (8)	0.065 (6)	0.188 (16)	0.005 (6)	0.093 (10)	0.005 (9)
C7	0.060 (6)	0.107 (10)	0.113 (11)	0.008 (7)	0.028 (7)	0.028 (9)
C8	0.057 (5)	0.111 (10)	0.085 (8)	−0.001 (7)	0.017 (5)	0.003 (8)
C9	0.047 (4)	0.085 (7)	0.069 (6)	−0.001 (5)	0.015 (4)	−0.006 (5)
C10	0.042 (3)	0.052 (4)	0.048 (4)	−0.004 (3)	0.010 (3)	−0.002 (3)
C11	0.038 (3)	0.073 (6)	0.049 (4)	0.005 (3)	0.009 (3)	0.010 (4)
C12	0.045 (4)	0.071 (5)	0.037 (3)	0.002 (4)	0.004 (3)	0.007 (3)
C13	0.040 (3)	0.045 (3)	0.037 (3)	−0.004 (3)	0.011 (3)	0.006 (3)
C14	0.049 (4)	0.047 (3)	0.041 (3)	−0.001 (3)	0.015 (3)	0.002 (3)
C15	0.057 (4)	0.047 (4)	0.040 (4)	0.000 (3)	0.016 (3)	−0.004 (3)
C16	0.063 (5)	0.063 (5)	0.048 (4)	−0.011 (4)	0.013 (4)	−0.001 (4)
C17	0.074 (6)	0.079 (6)	0.050 (5)	−0.003 (5)	0.005 (4)	−0.019 (5)
C18	0.104 (9)	0.087 (8)	0.040 (4)	0.004 (7)	0.021 (5)	0.001 (5)
C19	0.128 (10)	0.060 (5)	0.058 (5)	−0.010 (6)	0.048 (6)	−0.008 (5)
C20	0.091 (7)	0.051 (4)	0.052 (4)	−0.006 (4)	0.033 (4)	−0.004 (4)
C21	0.050 (4)	0.070 (5)	0.057 (5)	0.000 (4)	0.022 (4)	−0.003 (4)
C22	0.039 (4)	0.072 (6)	0.057 (5)	−0.006 (4)	0.008 (3)	−0.003 (4)
C23	0.040 (3)	0.042 (3)	0.040 (3)	−0.001 (3)	0.007 (3)	−0.001 (3)
C24	0.047 (4)	0.044 (3)	0.039 (3)	−0.002 (3)	0.003 (3)	0.007 (3)

Geometric parameters (Å, º) top

I1—Hg1	2.6441 (8)	C11—H11	0.9300
I2—Hg1	2.6555 (9)	C12—C13	1.415 (11)
N1—Hg1	2.425 (7)	C12—H12	0.9300
N2—Hg1	2.399 (7)	C13—C23	1.407 (10)
C1—N1	1.312 (12)	C13—C14	1.426 (10)
C1—C2	1.364 (15)	C14—C21	1.379 (12)
C1—H1	0.9300	C14—C15	1.487 (11)
C2—C3	1.372 (14)	C15—C20	1.389 (12)
C2—H2	0.9300	C15—C16	1.394 (12)
C3—C10	1.420 (12)	C16—C17	1.398 (13)
C3—C4	1.493 (13)	C16—H16	0.9300
C4—C9	1.382 (15)	C17—C18	1.380 (18)
C4—C5	1.401 (14)	C17—H17	0.9300
C5—C6	1.409 (19)	C18—C19	1.393 (18)
C5—H5	0.9300	C18—H18	0.9300
C6—C7	1.40 (2)	C19—C20	1.383 (15)
C6—H6	0.9300	C19—H19	0.9300
C7—C8	1.34 (2)	C20—H20	0.9300
C7—H7	0.9300	C21—C22	1.381 (14)
C8—C9	1.378 (15)	C21—H21	0.9300
C8—H8	0.9300	C22—N2	1.320 (12)
C9—H9	0.9300	C22—H22	0.9300
C10—C24	1.419 (11)	C23—N2	1.379 (10)
C10—C11	1.423 (12)	C23—C24	1.447 (11)
C11—C12	1.345 (13)	C24—N1	1.352 (10)

N2—Hg1—N1	69.4 (2)	C12—C11—C10	121.7 (8)
N2—Hg1—I1	104.08 (17)	C12—C11—H11	119.1
N1—Hg1—I1	110.65 (19)	C10—C11—H11	119.1
N2—Hg1—I2	107.53 (17)	C11—C12—C13	121.5 (7)
N1—Hg1—I2	103.11 (19)	C11—C12—H12	119.2
I1—Hg1—I2	139.97 (3)	C13—C12—H12	119.2
C1—N1—C24	118.5 (8)	C23—C13—C12	118.2 (7)
C1—N1—Hg1	125.3 (6)	C23—C13—C14	118.5 (7)
C24—N1—Hg1	115.9 (6)	C12—C13—C14	123.0 (7)
C22—N2—C23	117.4 (7)	C21—C14—C13	117.8 (7)
C22—N2—Hg1	125.6 (6)	C21—C14—C15	121.5 (7)
C23—N2—Hg1	116.8 (5)	C13—C14—C15	120.7 (7)
N1—C1—C2	122.9 (8)	C20—C15—C16	119.2 (8)
N1—C1—H1	118.6	C20—C15—C14	120.0 (8)
C2—C1—H1	118.6	C16—C15—C14	120.8 (8)
C1—C2—C3	121.6 (8)	C15—C16—C17	120.3 (9)
C1—C2—H2	119.2	C15—C16—H16	119.8
C3—C2—H2	119.2	C17—C16—H16	119.8
C2—C3—C10	117.4 (8)	C18—C17—C16	120.0 (11)
C2—C3—C4	121.8 (8)	C18—C17—H17	120.0
C10—C3—C4	120.8 (8)	C16—C17—H17	120.0
C9—C4—C5	118.6 (9)	C17—C18—C19	119.7 (10)
C9—C4—C3	121.9 (8)	C17—C18—H18	120.2
C5—C4—C3	119.5 (9)	C19—C18—H18	120.2
C4—C5—C6	118.6 (12)	C20—C19—C18	120.4 (10)
C4—C5—H5	120.7	C20—C19—H19	119.8
C6—C5—H5	120.7	C18—C19—H19	119.8
C7—C6—C5	120.5 (11)	C19—C20—C15	120.3 (10)
C7—C6—H6	119.8	C19—C20—H20	119.8
C5—C6—H6	119.8	C15—C20—H20	119.8
C8—C7—C6	119.7 (12)	C14—C21—C22	119.8 (8)
C8—C7—H7	120.1	C14—C21—H21	120.1
C6—C7—H7	120.1	C22—C21—H21	120.1
C7—C8—C9	120.5 (14)	N2—C22—C21	124.5 (8)
C7—C8—H8	119.8	N2—C22—H22	117.7
C9—C8—H8	119.8	C21—C22—H22	117.7
C8—C9—C4	122.0 (11)	N2—C23—C13	121.9 (7)
C8—C9—H9	119.0	N2—C23—C24	117.6 (7)
C4—C9—H9	119.0	C13—C23—C24	120.5 (7)
C24—C10—C3	117.0 (8)	N1—C24—C10	122.6 (8)
C24—C10—C11	118.7 (7)	N1—C24—C23	119.2 (7)
C3—C10—C11	124.2 (8)	C10—C24—C23	118.2 (7)

C1—N1—Hg1—N2	−177.4 (9)	C21—C14—C15—C20	51.1 (12)
C24—N1—Hg1—N2	9.2 (6)	C13—C14—C15—C20	−129.9 (9)
C1—N1—Hg1—I1	−79.6 (9)	C21—C14—C15—C16	−130.2 (10)
C24—N1—Hg1—I1	107.0 (6)	C13—C14—C15—C16	48.7 (12)
C1—N1—Hg1—I2	78.6 (9)	C20—C15—C16—C17	0.7 (15)
C24—N1—Hg1—I2	−94.9 (6)	C14—C15—C16—C17	−177.9 (9)
C22—N2—Hg1—N1	177.5 (8)	C15—C16—C17—C18	1.3 (17)
C23—N2—Hg1—N1	−7.5 (5)	C16—C17—C18—C19	−1.3 (19)
C22—N2—Hg1—I1	70.4 (8)	C17—C18—C19—C20	−0.7 (19)
C23—N2—Hg1—I1	−114.6 (5)	C18—C19—C20—C15	2.8 (17)
C22—N2—Hg1—I2	−84.7 (7)	C16—C15—C20—C19	−2.7 (15)
C23—N2—Hg1—I2	90.3 (6)	C14—C15—C20—C19	175.9 (9)
N1—C1—C2—C3	0.8 (19)	C13—C14—C21—C22	0.4 (14)
C1—C2—C3—C10	1.2 (16)	C15—C14—C21—C22	179.4 (9)
C1—C2—C3—C4	−178.3 (10)	C14—C21—C22—N2	−3.1 (16)
C2—C3—C4—C9	130.8 (11)	C12—C13—C23—N2	171.4 (8)
C10—C3—C4—C9	−48.7 (14)	C14—C13—C23—N2	−2.7 (11)
C2—C3—C4—C5	−47.7 (14)	C12—C13—C23—C24	−9.3 (11)
C10—C3—C4—C5	132.8 (10)	C14—C13—C23—C24	176.6 (7)
C9—C4—C5—C6	4.5 (17)	C3—C10—C24—N1	3.7 (13)
C3—C4—C5—C6	−177.0 (10)	C11—C10—C24—N1	−175.7 (8)
C4—C5—C6—C7	−4 (2)	C3—C10—C24—C23	−174.0 (7)
C5—C6—C7—C8	1 (2)	C11—C10—C24—C23	6.7 (12)
C6—C7—C8—C9	1 (2)	N2—C23—C24—N1	3.3 (11)
C7—C8—C9—C4	−1 (2)	C13—C23—C24—N1	−176.0 (7)
C5—C4—C9—C8	−2.2 (18)	N2—C23—C24—C10	−179.0 (7)
C3—C4—C9—C8	179.3 (12)	C13—C23—C24—C10	1.7 (11)
C2—C3—C10—C24	−3.3 (13)	C21—C22—N2—C23	2.8 (14)
C4—C3—C10—C24	176.3 (8)	C21—C22—N2—Hg1	177.8 (7)
C2—C3—C10—C11	176.0 (9)	C13—C23—N2—C22	0.2 (12)
C4—C3—C10—C11	−4.4 (14)	C24—C23—N2—C22	−179.2 (8)
C24—C10—C11—C12	−7.6 (14)	C13—C23—N2—Hg1	−175.2 (6)
C3—C10—C11—C12	173.1 (9)	C24—C23—N2—Hg1	5.5 (9)
C10—C11—C12—C13	−0.1 (15)	C2—C1—N1—C24	−0.6 (16)
C11—C12—C13—C23	8.6 (13)	C2—C1—N1—Hg1	−173.9 (9)
C11—C12—C13—C14	−177.5 (9)	C10—C24—N1—C1	−1.7 (14)
C23—C13—C14—C21	2.3 (12)	C23—C24—N1—C1	175.9 (9)
C12—C13—C14—C21	−171.5 (8)	C10—C24—N1—Hg1	172.2 (6)
C23—C13—C14—C15	−176.7 (7)	C23—C24—N1—Hg1	−10.2 (10)
C12—C13—C14—C15	9.5 (12)

Experimental details

Crystal data
Chemical formula	[HgI₂(C₂₄H₁₆N₂)]
M_r	786.78
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	16.673 (3), 8.8964 (18), 16.823 (3)
β (°)	109.26 (3)
V (Å³)	2355.7 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	9.17
Crystal size (mm)	0.50 × 0.48 × 0.28

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Numerical shape of crystal determined optically
T_min, T_max	0.016, 0.080
No. of measured, independent and observed [I > 2σ(I)] reflections	19129, 6340, 5356
R_int	0.094
(sin θ/λ)_max (Å⁻¹)	0.689

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.183, 1.23
No. of reflections	6340
No. of parameters	263
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.49, −1.11

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

I1—Hg1	2.6441 (8)	N1—Hg1	2.425 (7)
I2—Hg1	2.6555 (9)	N2—Hg1	2.399 (7)

N2—Hg1—N1	69.4 (2)	N2—Hg1—I2	107.53 (17)
N2—Hg1—I1	104.08 (17)	N1—Hg1—I2	103.11 (19)
N1—Hg1—I1	110.65 (19)	I1—Hg1—I2	139.97 (3)

Acknowledgements

We are grateful to the Islamic Azad University, Shahr-e-Rey Branch, for financial support.

References

Ahmadi, R., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1156–m1157. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Ahmadi, R., Kalateh, K., Abedi, A., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1306–m1307. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ahmadi, R., Kalateh, K., Ebadi, A., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1266. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ahmadi, R., Khalighi, A., Kalateh, K., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1233. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, W. T., Wang, M. S., Liu, X., Guo, G. C. & Huang, J. S. (2006). Cryst. Growth Des. 6, 2289–2300. Web of Science CSD CrossRef CAS 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
Freire, E., Baggio, S., Baggio, R. & Suescun, L. (1999). J. Chem. Crystallogr. 29, 825–830. Web of Science CSD CrossRef CAS Google Scholar
Htoon, S. & Ladd, M. F. C. (1976). J. Cryst. Mol. Struct. 6, 55–58. CSD CrossRef CAS Web of Science Google Scholar
Khalighi, A., Ahmadi, R., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1211–m1212. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Khavasi, H. R., Abedi, A., Amani, V., Notash, B. & Safari, N. (2008). Polyhedron, 27, 1848–1854. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2005). X-RED and X-SHAPE. Stoe & Cie, Darmstadt, Germany 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
Yousefi, M., Khalighi, A., Tadayon Pour, N., Amani, V. & Khavasi, H. R. (2008). Acta Cryst. E64, m1284–m1285. 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