Di-μ-chlorido-bis-({2-[(4-bromo-phen-yl)-imino-meth-yl]pyridine-κN,N'}-chloridomercury(II)).

The unique Hg(II) ion in the title centrosymmetric dinuclear complex, [Hg(2)Cl(4)(C(12)H(9)BrN(2))(2)], is in a distorted trigonal-bipyramidal coordination environment formed by the bis-chelating N-heterocyclic ligand, two bridging Cl atoms and one terminal Cl atom. One of the bridging Hg-Cl bonds is significantly longer than the other.

Related literature

For background information on diimine complexes, see: Dehghanpour & Mahmoudi (2007 ▶); Dehghanpour, Mahmoudi, Khalaj & Salmanpour (2007 ▶). For related crystal structures, see: Mahmoudi et al. (2009 ▶); Dehghanpour, Mahmoudi, Khalaj, Salmanpour & Adib (2007 ▶).

Experimental

Crystal data

[Hg2Cl4(C12H9BrN2)2]

M = 1065.22

Monoclinic,

a = 7.6697 (2) Å

b = 15.0247 (4) Å

c = 12.2129 (4) Å

β = 96.738 (1)°

V = 1397.63 (7) Å3

Z = 2

Mo Kα radiation

μ = 14.24 mm−1

T = 100 K

0.10 × 0.10 × 0.05 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (APEX2; Bruker, 2005 ▶) T min = 0.280, T max = 0.491

17922 measured reflections

4047 independent reflections

3636 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.019

wR(F 2) = 0.041

S = 1.01

4047 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.97 e Å−3

Δρmin = −1.15 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809025641/lh2844sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809025641/lh2844Isup2.hkl

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

[Hg2Cl4(C12H9BrN2)2]	F(000) = 976
Mr = 1065.22	Dx = 2.531 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8129 reflections
a = 7.6697 (2) Å	θ = 2.2–29.7°
b = 15.0247 (4) Å	µ = 14.24 mm−1
c = 12.2129 (4) Å	T = 100 K
β = 96.738 (1)°	Prism, yellow
V = 1397.63 (7) Å3	0.10 × 0.10 × 0.05 mm
Z = 2

Bruker SMART APEXII CCD area-detector diffractometer	4047 independent reflections
Radiation source: fine-focus sealed tube	3636 reflections with I > 2σ(I)
graphite	Rint = 0.032
Detector resolution: 0 pixels mm-1	θmax = 30.0°, θmin = 2.2°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (APEX2; Bruker, 2005)	k = −21→20
Tmin = 0.280, Tmax = 0.491	l = −17→17
17922 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)] = 0.019	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.041	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.015P)2 + 1.35P] where P = (Fo2 + 2Fc2)/3
4047 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 0.97 e Å−3
0 restraints	Δρmin = −1.15 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	0.170956 (13)	0.446982 (7)	0.108289 (9)	0.02080 (3)
Br1	0.86964 (5)	0.10383 (2)	−0.01114 (3)	0.04340 (9)
Cl1	0.42148 (9)	0.53787 (4)	0.15929 (7)	0.03126 (16)
Cl2	0.04621 (9)	0.39647 (4)	−0.07921 (5)	0.02143 (12)
N1	0.2551 (3)	0.29234 (14)	0.15931 (18)	0.0183 (4)
N2	−0.0272 (3)	0.38863 (15)	0.21855 (18)	0.0192 (4)
C1	−0.0010 (3)	0.30362 (17)	0.2535 (2)	0.0192 (5)
C2	−0.1169 (4)	0.26078 (18)	0.3146 (2)	0.0207 (5)
H2A	−0.0974	0.2006	0.3366	0.025*
C3	−0.2618 (4)	0.30668 (18)	0.3433 (2)	0.0219 (5)
H3A	−0.3420	0.2788	0.3861	0.026*
C4	−0.2871 (4)	0.39390 (18)	0.3083 (2)	0.0218 (5)
H4A	−0.3842	0.4272	0.3275	0.026*
C5	−0.1679 (4)	0.43198 (18)	0.2445 (2)	0.0209 (5)
H5A	−0.1878	0.4911	0.2184	0.025*
C6	0.1522 (4)	0.25556 (18)	0.2214 (2)	0.0212 (5)
H6A	0.1752	0.1965	0.2471	0.025*
C7	0.3966 (3)	0.24488 (18)	0.1221 (2)	0.0194 (5)
C8	0.4078 (4)	0.15213 (19)	0.1228 (2)	0.0239 (5)
H8A	0.3193	0.1175	0.1508	0.029*
C9	0.5489 (4)	0.1107 (2)	0.0824 (2)	0.0270 (6)
H9A	0.5572	0.0476	0.0820	0.032*
C10	0.6778 (4)	0.1622 (2)	0.0425 (2)	0.0260 (6)
C11	0.6691 (4)	0.25420 (19)	0.0398 (2)	0.0230 (5)
H11A	0.7587	0.2884	0.0122	0.028*
C12	0.5255 (3)	0.29538 (18)	0.0786 (2)	0.0206 (5)
H12A	0.5151	0.3584	0.0756	0.025*

	U11	U22	U33	U12	U13	U23
Hg1	0.02163 (5)	0.01490 (5)	0.02590 (6)	−0.00157 (4)	0.00290 (4)	0.00198 (4)
Br1	0.04489 (19)	0.03626 (17)	0.0548 (2)	0.01823 (15)	0.03004 (17)	0.01083 (16)
Cl1	0.0233 (3)	0.0157 (3)	0.0531 (5)	−0.0016 (2)	−0.0027 (3)	−0.0017 (3)
Cl2	0.0274 (3)	0.0159 (3)	0.0210 (3)	0.0040 (2)	0.0029 (2)	0.0000 (2)
N1	0.0210 (10)	0.0147 (10)	0.0187 (10)	0.0018 (8)	0.0009 (8)	−0.0002 (8)
N2	0.0221 (10)	0.0163 (10)	0.0194 (10)	−0.0008 (8)	0.0028 (8)	0.0005 (8)
C1	0.0227 (12)	0.0171 (12)	0.0179 (12)	0.0002 (9)	0.0025 (10)	0.0003 (9)
C2	0.0278 (13)	0.0152 (12)	0.0189 (12)	−0.0014 (10)	0.0027 (10)	0.0027 (9)
C3	0.0248 (13)	0.0226 (13)	0.0188 (12)	−0.0017 (10)	0.0043 (10)	0.0028 (10)
C4	0.0234 (12)	0.0201 (12)	0.0221 (13)	0.0042 (10)	0.0034 (10)	0.0019 (10)
C5	0.0256 (13)	0.0170 (12)	0.0203 (12)	0.0028 (10)	0.0030 (10)	0.0031 (10)
C6	0.0271 (13)	0.0162 (12)	0.0202 (12)	0.0018 (10)	0.0030 (10)	0.0014 (10)
C7	0.0201 (11)	0.0202 (12)	0.0175 (12)	0.0025 (10)	0.0004 (9)	0.0005 (10)
C8	0.0281 (13)	0.0203 (13)	0.0244 (13)	0.0015 (11)	0.0071 (11)	0.0030 (11)
C9	0.0365 (15)	0.0199 (13)	0.0258 (14)	0.0089 (11)	0.0086 (12)	0.0027 (11)
C10	0.0283 (13)	0.0273 (14)	0.0236 (13)	0.0088 (11)	0.0077 (11)	0.0036 (11)
C11	0.0231 (12)	0.0252 (13)	0.0209 (12)	0.0008 (11)	0.0038 (10)	0.0014 (11)
C12	0.0225 (12)	0.0204 (12)	0.0187 (12)	0.0003 (10)	0.0017 (10)	0.0011 (10)

Hg1—N2	2.318 (2)	C3—H3A	0.9500
Hg1—Cl1	2.3799 (7)	C4—C5	1.392 (4)
Hg1—N1	2.472 (2)	C4—H4A	0.9500
Hg1—Cl2	2.4941 (7)	C5—H5A	0.9500
Hg1—Cl2i	2.8799 (6)	C6—H6A	0.9500
Br1—C10	1.894 (3)	C7—C8	1.396 (4)
Cl2—Hg1i	2.8799 (6)	C7—C12	1.399 (4)
N1—C6	1.282 (3)	C8—C9	1.389 (4)
N1—C7	1.418 (3)	C8—H8A	0.9500
N2—C5	1.330 (3)	C9—C10	1.388 (4)
N2—C1	1.354 (3)	C9—H9A	0.9500
C1—C2	1.384 (4)	C10—C11	1.385 (4)
C1—C6	1.471 (4)	C11—C12	1.394 (4)
C2—C3	1.387 (4)	C11—H11A	0.9500
C2—H2A	0.9500	C12—H12A	0.9500
C3—C4	1.385 (4)
N2—Hg1—Cl1	129.00 (6)	C3—C4—H4A	120.5
N2—Hg1—N1	70.58 (7)	C5—C4—H4A	120.5
Cl1—Hg1—N1	107.12 (5)	N2—C5—C4	122.4 (2)
N2—Hg1—Cl2	102.20 (6)	N2—C5—H5A	118.8
Cl1—Hg1—Cl2	128.74 (3)	C4—C5—H5A	118.8
N1—Hg1—Cl2	90.35 (5)	N1—C6—C1	120.8 (2)
N2—Hg1—Cl2i	88.36 (6)	N1—C6—H6A	119.6
Cl1—Hg1—Cl2i	90.07 (2)	C1—C6—H6A	119.6
N1—Hg1—Cl2i	158.28 (5)	C8—C7—C12	119.9 (2)
Cl2—Hg1—Cl2i	88.926 (19)	C8—C7—N1	123.3 (2)
Hg1—Cl2—Hg1i	91.074 (19)	C12—C7—N1	116.8 (2)
C6—N1—C7	121.4 (2)	C9—C8—C7	119.7 (3)
C6—N1—Hg1	113.18 (17)	C9—C8—H8A	120.2
C7—N1—Hg1	125.39 (17)	C7—C8—H8A	120.2
C5—N2—C1	118.8 (2)	C10—C9—C8	119.4 (3)
C5—N2—Hg1	123.96 (18)	C10—C9—H9A	120.3
C1—N2—Hg1	117.19 (17)	C8—C9—H9A	120.3
N2—C1—C2	121.8 (2)	C11—C10—C9	122.1 (3)
N2—C1—C6	118.2 (2)	C11—C10—Br1	119.4 (2)
C2—C1—C6	119.9 (2)	C9—C10—Br1	118.5 (2)
C1—C2—C3	119.3 (2)	C10—C11—C12	118.2 (3)
C1—C2—H2A	120.4	C10—C11—H11A	120.9
C3—C2—H2A	120.4	C12—C11—H11A	120.9
C4—C3—C2	118.6 (2)	C11—C12—C7	120.7 (3)
C4—C3—H3A	120.7	C11—C12—H12A	119.7
C2—C3—H3A	120.7	C7—C12—H12A	119.7
C3—C4—C5	119.0 (2)
N2—Hg1—Cl2—Hg1i	88.09 (6)	C6—C1—C2—C3	−179.4 (2)
Cl1—Hg1—Cl2—Hg1i	−89.22 (3)	C1—C2—C3—C4	0.9 (4)
N1—Hg1—Cl2—Hg1i	158.29 (5)	C2—C3—C4—C5	0.8 (4)
Cl2i—Hg1—Cl2—Hg1i	0.0	C1—N2—C5—C4	1.5 (4)
N2—Hg1—N1—C6	−0.60 (18)	Hg1—N2—C5—C4	178.0 (2)
Cl1—Hg1—N1—C6	125.53 (18)	C3—C4—C5—N2	−2.1 (4)
Cl2—Hg1—N1—C6	−103.42 (18)	C7—N1—C6—C1	−175.9 (2)
Cl2i—Hg1—N1—C6	−15.4 (3)	Hg1—N1—C6—C1	1.6 (3)
N2—Hg1—N1—C7	176.8 (2)	N2—C1—C6—N1	−2.1 (4)
Cl1—Hg1—N1—C7	−57.1 (2)	C2—C1—C6—N1	175.8 (3)
Cl2—Hg1—N1—C7	73.94 (19)	C6—N1—C7—C8	18.2 (4)
Cl2i—Hg1—N1—C7	161.92 (14)	Hg1—N1—C7—C8	−159.0 (2)
Cl1—Hg1—N2—C5	86.3 (2)	C6—N1—C7—C12	−164.6 (2)
N1—Hg1—N2—C5	−177.1 (2)	Hg1—N1—C7—C12	18.3 (3)
Cl2—Hg1—N2—C5	−91.0 (2)	C12—C7—C8—C9	1.3 (4)
Cl2i—Hg1—N2—C5	−2.5 (2)	N1—C7—C8—C9	178.5 (3)
Cl1—Hg1—N2—C1	−97.14 (19)	C7—C8—C9—C10	0.5 (4)
N1—Hg1—N2—C1	−0.46 (18)	C8—C9—C10—C11	−1.1 (5)
Cl2—Hg1—N2—C1	85.56 (18)	C8—C9—C10—Br1	179.6 (2)
Cl2i—Hg1—N2—C1	174.10 (18)	C9—C10—C11—C12	0.0 (4)
C5—N2—C1—C2	0.4 (4)	Br1—C10—C11—C12	179.3 (2)
Hg1—N2—C1—C2	−176.4 (2)	C10—C11—C12—C7	1.8 (4)
C5—N2—C1—C6	178.2 (2)	C8—C7—C12—C11	−2.5 (4)
Hg1—N2—C1—C6	1.4 (3)	N1—C7—C12—C11	−179.8 (2)
N2—C1—C2—C3	−1.6 (4)

Hg1—N2	2.318 (2)
Hg1—Cl1	2.3799 (7)
Hg1—N1	2.472 (2)
Hg1—Cl2	2.4941 (7)
Hg1—Cl2i	2.8799 (6)

N2—Hg1—Cl1	129.00 (6)
N2—Hg1—N1	70.58 (7)
Cl1—Hg1—N1	107.12 (5)
N2—Hg1—Cl2	102.20 (6)
Cl1—Hg1—Cl2	128.74 (3)
N1—Hg1—Cl2	90.35 (5)
N2—Hg1—Cl2i	88.36 (6)
Cl1—Hg1—Cl2i	90.07 (2)
N1—Hg1—Cl2i	158.28 (5)
Cl2—Hg1—Cl2i	88.926 (19)
Hg1—Cl2—Hg1i	91.074 (19)

Symmetry code: (i) .