(4,7-Diphenyl-1,10-phenanthroline-κN,N')diiodidomercury(II).

In the mol-ecule of the title compound, [HgI(2)(C(24)H(16)N(2))], the Hg(II) atom is four-coordinated in a distorted tetra-hedral 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 = 786.78

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.183

S = 1.23

6340 reflections

263 parameters

H-atom parameters constrained

Δρmax = 1.49 e Å−3

Δρmin = −1.10 e Å−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 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680803081X/hk2540sup1.cif

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

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

[HgI2(C24H16N2)]	F(000) = 1440
Mr = 786.78	Dx = 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

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

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(Fo2) + (0.085P)2 + 4.523P] where P = (Fo2 + 2Fc2)/3
S = 1.23	(Δ/σ)max = 0.009
6340 reflections	Δρmax = 1.49 e Å−3
263 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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)