Dichloridobis[1-(2-methyl-benzimidazol-1-ylmethyl-κN)benzotriazole]mercury(II).

In the title compound, [HgCl(2)(C(15)H(13)N(5))(2)], the Hg(II) atom is located on a twofold rotation axis and resides in a distorted tetra-hedral coordination environment composed of two Cl atoms and two N atoms from two 1-(2-methyl-benzimidazol-1-ylmeth-yl)benzotriazole ligands.

Related literature

For metal complexes of similar N-heterocyclic ligands, see: Fan et al. (2003 ▶); Hoskins et al. (1997 ▶); Makoto et al. (2005 ▶)

Experimental

Crystal data

[HgCl2(C15H13N5)2]

M = 798.10

Monoclinic,

a = 15.612 (3) Å

b = 12.883 (3) Å

c = 14.751 (3) Å

β = 97.49 (3)°

V = 2941.5 (11) Å3

Z = 4

Mo Kα radiation

μ = 5.46 mm−1

T = 293 K

0.22 × 0.18 × 0.16 mm

Data collection

Rigaku Saturn724 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006 ▶) T min = 0.380, T max = 0.476 (expected range = 0.334–0.418)

14609 measured reflections

2587 independent reflections

2379 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.062

S = 1.09

2587 reflections

196 parameters

H-atom parameters constrained

Δρmax = 0.57 e Å−3

Δρmin = −0.47 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2006 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809023459/ng2600sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809023459/ng2600Isup2.hkl

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

[HgCl2(C15H13N5)2]	F(000) = 1560
Mr = 798.10	Dx = 1.802 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4239 reflections
a = 15.612 (3) Å	θ = 2.1–29.1°
b = 12.883 (3) Å	µ = 5.46 mm−1
c = 14.751 (3) Å	T = 293 K
β = 97.49 (3)°	Prism, colorless
V = 2941.5 (11) Å3	0.22 × 0.18 × 0.16 mm
Z = 4

Rigaku Saturn724 diffractometer	2587 independent reflections
Radiation source: fine-focus sealed tube	2379 reflections with I > 2σ(I)
graphite	Rint = 0.051
Detector resolution: 28.5714 pixels mm-1	θmax = 25.0°, θmin = 2.4°
dtprofit.ref scans	h = −18→18
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006)	k = −15→15
Tmin = 0.380, Tmax = 0.476	l = −17→17
14609 measured reflections

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.062	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0229P)2 + 4.6614P] where P = (Fo2 + 2Fc2)/3
2587 reflections	(Δ/σ)max < 0.001
196 parameters	Δρmax = 0.57 e Å−3
0 restraints	Δρmin = −0.47 e Å−3

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	0.5000	−0.10389 (2)	0.2500	0.04638 (11)
Cl1	0.62989 (9)	−0.19849 (10)	0.30815 (8)	0.0585 (4)
N1	0.4757 (2)	0.0231 (3)	0.3545 (2)	0.0389 (9)
N2	0.4113 (2)	0.1501 (3)	0.4213 (2)	0.0380 (9)
N3	0.3561 (2)	0.3232 (3)	0.4176 (2)	0.0439 (10)
N4	0.3539 (3)	0.3999 (4)	0.4808 (3)	0.0606 (12)
N5	0.3651 (3)	0.4882 (4)	0.4425 (3)	0.0642 (13)
C1	0.3170 (3)	0.0391 (4)	0.3110 (4)	0.0577 (14)
H1A	0.3243	−0.0205	0.2737	0.087*
H1B	0.2941	0.0956	0.2728	0.087*
H1C	0.2778	0.0226	0.3538	0.087*
C2	0.4021 (3)	0.0696 (4)	0.3614 (3)	0.0392 (11)
C3	0.5386 (3)	0.0762 (3)	0.4139 (3)	0.0359 (11)
C4	0.6271 (3)	0.0600 (4)	0.4337 (3)	0.0436 (11)
H4	0.6547	0.0066	0.4064	0.052*
C5	0.6722 (3)	0.1269 (4)	0.4956 (3)	0.0513 (13)
H5	0.7317	0.1191	0.5095	0.062*
C6	0.6311 (3)	0.2054 (4)	0.5377 (3)	0.0541 (13)
H6	0.6637	0.2481	0.5799	0.065*
C7	0.5436 (3)	0.2220 (4)	0.5189 (3)	0.0452 (12)
H7	0.5163	0.2750	0.5469	0.054*
C8	0.4984 (3)	0.1560 (3)	0.4564 (3)	0.0348 (10)
C9	0.3430 (3)	0.2172 (4)	0.4447 (3)	0.0471 (12)
H9A	0.2878	0.1926	0.4145	0.057*
H9B	0.3414	0.2146	0.5102	0.057*
C10	0.3696 (3)	0.3647 (4)	0.3355 (3)	0.0420 (11)
C11	0.3763 (3)	0.3232 (5)	0.2497 (3)	0.0568 (14)
H11	0.3719	0.2523	0.2381	0.068*
C12	0.3900 (3)	0.3936 (5)	0.1833 (4)	0.0636 (16)
H12	0.3946	0.3697	0.1246	0.076*
C13	0.3973 (3)	0.5008 (6)	0.2009 (4)	0.0688 (17)
H13	0.4074	0.5456	0.1539	0.083*
C14	0.3898 (3)	0.5404 (5)	0.2845 (4)	0.0642 (16)
H14	0.3943	0.6114	0.2959	0.077*
C15	0.3752 (3)	0.4707 (4)	0.3524 (3)	0.0496 (13)

	U11	U22	U33	U12	U13	U23
Hg1	0.05294 (19)	0.03316 (15)	0.05032 (18)	0.000	−0.00348 (13)	0.000
Cl1	0.0714 (9)	0.0507 (8)	0.0509 (7)	0.0232 (7)	−0.0012 (7)	0.0044 (6)
N1	0.039 (2)	0.034 (2)	0.044 (2)	0.0053 (18)	0.0057 (18)	−0.0056 (17)
N2	0.035 (2)	0.039 (2)	0.040 (2)	0.0014 (17)	0.0063 (18)	−0.0022 (18)
N3	0.050 (2)	0.045 (2)	0.037 (2)	0.0158 (19)	0.0079 (19)	−0.0040 (19)
N4	0.080 (3)	0.058 (3)	0.045 (2)	0.023 (3)	0.011 (2)	−0.010 (2)
N5	0.085 (4)	0.048 (3)	0.060 (3)	0.014 (3)	0.006 (3)	−0.003 (2)
C1	0.042 (3)	0.063 (4)	0.064 (3)	−0.001 (3)	−0.005 (3)	−0.013 (3)
C2	0.040 (3)	0.040 (3)	0.038 (3)	−0.005 (2)	0.004 (2)	0.001 (2)
C3	0.041 (3)	0.034 (2)	0.032 (2)	−0.002 (2)	0.003 (2)	−0.0002 (19)
C4	0.036 (3)	0.046 (3)	0.049 (3)	0.004 (2)	0.007 (2)	−0.004 (2)
C5	0.038 (3)	0.057 (3)	0.058 (3)	−0.006 (2)	0.005 (2)	−0.001 (3)
C6	0.054 (3)	0.057 (3)	0.049 (3)	−0.010 (3)	−0.001 (3)	−0.010 (3)
C7	0.051 (3)	0.039 (3)	0.046 (3)	0.001 (2)	0.007 (2)	−0.006 (2)
C8	0.040 (3)	0.032 (2)	0.032 (2)	−0.001 (2)	0.005 (2)	0.001 (2)
C9	0.044 (3)	0.056 (3)	0.045 (3)	0.012 (2)	0.018 (2)	0.000 (2)
C10	0.034 (3)	0.054 (3)	0.039 (3)	0.009 (2)	0.007 (2)	−0.001 (2)
C11	0.053 (3)	0.074 (4)	0.043 (3)	0.009 (3)	0.007 (3)	−0.004 (3)
C12	0.047 (3)	0.107 (5)	0.036 (3)	0.005 (3)	0.004 (2)	−0.002 (3)
C13	0.043 (3)	0.094 (5)	0.068 (4)	0.001 (3)	0.001 (3)	0.033 (4)
C14	0.050 (3)	0.064 (4)	0.076 (4)	0.006 (3)	−0.001 (3)	0.016 (3)
C15	0.047 (3)	0.054 (3)	0.047 (3)	0.014 (3)	0.002 (2)	0.003 (3)

Hg1—N1	2.313 (3)	C4—C5	1.380 (7)
Hg1—N1i	2.313 (3)	C4—H4	0.9300
Hg1—Cl1i	2.4248 (13)	C5—C6	1.387 (7)
Hg1—Cl1	2.4248 (13)	C5—H5	0.9300
N1—C2	1.311 (5)	C6—C7	1.375 (6)
N1—C3	1.405 (5)	C6—H6	0.9300
N2—C2	1.357 (6)	C7—C8	1.378 (6)
N2—C8	1.392 (5)	C7—H7	0.9300
N2—C9	1.450 (5)	C9—H9A	0.9700
N3—N4	1.362 (5)	C9—H9B	0.9700
N3—C10	1.366 (6)	C10—C15	1.389 (7)
N3—C9	1.444 (6)	C10—C11	1.390 (6)
N4—N5	1.293 (6)	C11—C12	1.372 (7)
N5—C15	1.377 (6)	C11—H11	0.9300
C1—C2	1.488 (6)	C12—C13	1.407 (8)
C1—H1A	0.9600	C12—H12	0.9300
C1—H1B	0.9600	C13—C14	1.354 (8)
C1—H1C	0.9600	C13—H13	0.9300
C3—C4	1.391 (6)	C14—C15	1.387 (7)
C3—C8	1.395 (6)	C14—H14	0.9300
N1—Hg1—N1i	89.97 (18)	C6—C5—H5	119.1
N1—Hg1—Cl1i	112.90 (10)	C7—C6—C5	121.8 (5)
N1i—Hg1—Cl1i	108.78 (10)	C7—C6—H6	119.1
N1—Hg1—Cl1	108.78 (10)	C5—C6—H6	119.1
N1i—Hg1—Cl1	112.90 (10)	C6—C7—C8	116.6 (4)
Cl1i—Hg1—Cl1	119.65 (7)	C6—C7—H7	121.7
C2—N1—C3	106.1 (4)	C8—C7—H7	121.7
C2—N1—Hg1	126.6 (3)	C7—C8—N2	132.3 (4)
C3—N1—Hg1	126.7 (3)	C7—C8—C3	122.3 (4)
C2—N2—C8	107.5 (4)	N2—C8—C3	105.4 (4)
C2—N2—C9	126.3 (4)	N3—C9—N2	111.3 (4)
C8—N2—C9	126.2 (4)	N3—C9—H9A	109.4
N4—N3—C10	110.1 (4)	N2—C9—H9A	109.4
N4—N3—C9	118.7 (4)	N3—C9—H9B	109.4
C10—N3—C9	131.2 (4)	N2—C9—H9B	109.4
N5—N4—N3	108.8 (4)	H9A—C9—H9B	108.0
N4—N5—C15	108.4 (4)	N3—C10—C15	103.8 (4)
C2—C1—H1A	109.5	N3—C10—C11	134.1 (5)
C2—C1—H1B	109.5	C15—C10—C11	122.1 (5)
H1A—C1—H1B	109.5	C12—C11—C10	115.7 (5)
C2—C1—H1C	109.5	C12—C11—H11	122.2
H1A—C1—H1C	109.5	C10—C11—H11	122.2
H1B—C1—H1C	109.5	C11—C12—C13	122.2 (5)
N1—C2—N2	112.3 (4)	C11—C12—H12	118.9
N1—C2—C1	125.1 (4)	C13—C12—H12	118.9
N2—C2—C1	122.6 (4)	C14—C13—C12	121.6 (5)
C4—C3—C8	120.6 (4)	C14—C13—H13	119.2
C4—C3—N1	130.7 (4)	C12—C13—H13	119.2
C8—C3—N1	108.7 (4)	C13—C14—C15	117.1 (6)
C5—C4—C3	116.9 (4)	C13—C14—H14	121.4
C5—C4—H4	121.6	C15—C14—H14	121.4
C3—C4—H4	121.6	N5—C15—C14	129.9 (5)
C4—C5—C6	121.8 (5)	N5—C15—C10	108.8 (4)
C4—C5—H5	119.1	C14—C15—C10	121.3 (5)
N1i—Hg1—N1—C2	86.5 (4)	C9—N2—C8—C7	−0.3 (8)
Cl1i—Hg1—N1—C2	−24.0 (4)	C2—N2—C8—C3	0.3 (5)
Cl1—Hg1—N1—C2	−159.3 (3)	C9—N2—C8—C3	−180.0 (4)
N1i—Hg1—N1—C3	−83.5 (3)	C4—C3—C8—C7	0.2 (7)
Cl1i—Hg1—N1—C3	166.0 (3)	N1—C3—C8—C7	179.9 (4)
Cl1—Hg1—N1—C3	30.7 (4)	C4—C3—C8—N2	179.9 (4)
C10—N3—N4—N5	0.3 (6)	N1—C3—C8—N2	−0.3 (5)
C9—N3—N4—N5	−178.6 (4)	N4—N3—C9—N2	−128.3 (4)
N3—N4—N5—C15	−0.3 (6)	C10—N3—C9—N2	53.1 (7)
C3—N1—C2—N2	0.0 (5)	C2—N2—C9—N3	−116.4 (5)
Hg1—N1—C2—N2	−171.7 (3)	C8—N2—C9—N3	63.9 (6)
C3—N1—C2—C1	−179.6 (4)	N4—N3—C10—C15	−0.2 (5)
Hg1—N1—C2—C1	8.7 (7)	C9—N3—C10—C15	178.5 (5)
C8—N2—C2—N1	−0.2 (5)	N4—N3—C10—C11	−179.2 (5)
C9—N2—C2—N1	−179.9 (4)	C9—N3—C10—C11	−0.4 (9)
C8—N2—C2—C1	179.4 (4)	N3—C10—C11—C12	179.7 (5)
C9—N2—C2—C1	−0.3 (7)	C15—C10—C11—C12	0.8 (7)
C2—N1—C3—C4	180.0 (5)	C10—C11—C12—C13	0.3 (8)
Hg1—N1—C3—C4	−8.4 (7)	C11—C12—C13—C14	−1.0 (8)
C2—N1—C3—C8	0.2 (5)	C12—C13—C14—C15	0.4 (8)
Hg1—N1—C3—C8	171.9 (3)	N4—N5—C15—C14	−179.2 (5)
C8—C3—C4—C5	−0.8 (7)	N4—N5—C15—C10	0.1 (6)
N1—C3—C4—C5	179.5 (4)	C13—C14—C15—N5	−180.0 (5)
C3—C4—C5—C6	1.2 (7)	C13—C14—C15—C10	0.8 (8)
C4—C5—C6—C7	−1.1 (8)	N3—C10—C15—N5	0.0 (5)
C5—C6—C7—C8	0.5 (7)	C11—C10—C15—N5	179.2 (4)
C6—C7—C8—N2	−179.7 (5)	N3—C10—C15—C14	179.4 (4)
C6—C7—C8—C3	0.0 (7)	C11—C10—C15—C14	−1.4 (8)
C2—N2—C8—C7	−180.0 (5)