Dibromidobis{1-[4-(pyridin-4-yl)phen-yl]ethanone-κN}mercury(II).

In the title compound, [HgBr(2)(C(13)H(11)NO)(2)], the Hg(II) atom adopts a four-coordinated HgN(2)Br(2) geometry, formed by two pyridine N atoms from two ligands and two bromide anions. The complex is located on a twofold axis. The coordination geometry is close to forming a see-saw (SS-4) polyhedron, the symmetry-related organic ligands being almost perpendicular; the dihedral angles between the two pyridine rings and between the two benzene rings are 85.5 (4) and 87.7 (4)°, respectively. Within the organic ligand, the pyridine ring is nearly coplanar with the benzene ring [dihedral angle = 13.1 (8)°]. In the crystal, the mol-ecular complexes are connected through weak inter-molecular C-H⋯Br contacts.

Related literature

For applications of coordination complexes bearing asymmetric ligands, see: Allendorf et al. (2009 ▶); Evans & Lin (2002 ▶); He et al. (2006 ▶); Hou et al. (2010 ▶). For examples of ligands based on a pyridyl ring, see: Fujita et al. (2005 ▶); Song et al. (2010 ▶).

Experimental

Crystal data

[HgBr2(C13H11NO)2]

M = 754.87

Monoclinic,

a = 16.656 (6) Å

b = 5.296 (2) Å

c = 29.442 (11) Å

β = 102.453 (6)°

V = 2535.8 (16) Å3

Z = 4

Mo Kα radiation

μ = 9.25 mm−1

T = 298 K

0.15 × 0.15 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2003 ▶) T min = 0.338, T max = 0.338

6208 measured reflections

2358 independent reflections

1339 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.131

S = 0.99

2358 reflections

151 parameters

25 restraints

H-atom parameters constrained

Δρmax = 1.03 e Å−3

Δρmin = −0.41 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811049993/bh2387sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811049993/bh2387Isup2.hkl

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

[HgBr2(C13H11NO)2]	F(000) = 1432
Mr = 754.87	Dx = 1.977 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1208 reflections
a = 16.656 (6) Å	θ = 2.5–18.6°
b = 5.296 (2) Å	µ = 9.25 mm−1
c = 29.442 (11) Å	T = 298 K
β = 102.453 (6)°	Block, colourless
V = 2535.8 (16) Å3	0.15 × 0.15 × 0.15 mm
Z = 4

Bruker SMART APEX diffractometer	2358 independent reflections
Radiation source: fine-focus sealed tube	1339 reflections with I > 2σ(I)
graphite	Rint = 0.047
φ and ω scans	θmax = 25.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −17→20
Tmin = 0.338, Tmax = 0.338	k = −6→6
6208 measured reflections	l = −35→30

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H-atom parameters constrained
S = 0.99	w = 1/[σ2(Fo2) + (0.0626P)2] where P = (Fo2 + 2Fc2)/3
2358 reflections	(Δ/σ)max = 0.001
151 parameters	Δρmax = 1.03 e Å−3
25 restraints	Δρmin = −0.41 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
Br1	1.09304 (9)	1.3414 (3)	0.69925 (5)	0.1331 (5)
C1	0.9296 (7)	0.848 (2)	0.6587 (5)	0.114 (4)
H1	0.9746	0.9148	0.6488	0.137*
C2	0.8806 (8)	0.675 (2)	0.6305 (5)	0.115 (4)
H2	0.8933	0.6333	0.6021	0.138*
C3	0.8158 (5)	0.5649 (18)	0.6421 (3)	0.069 (2)
C4	0.8052 (8)	0.640 (3)	0.6837 (5)	0.118 (4)
H4	0.7634	0.5656	0.6955	0.142*
C5	0.8535 (8)	0.823 (3)	0.7101 (4)	0.120 (4)
H5	0.8398	0.8759	0.7376	0.145*
C6	0.7626 (6)	0.3795 (17)	0.6137 (3)	0.073 (2)
C7	0.7812 (8)	0.257 (2)	0.5769 (5)	0.123 (4)
H7	0.8308	0.2937	0.5688	0.147*
C8	0.7310 (8)	0.081 (3)	0.5511 (5)	0.130 (5)
H8	0.7470	0.0032	0.5262	0.156*
C9	0.6581 (6)	0.0203 (17)	0.5617 (3)	0.079 (3)
C10	0.6395 (8)	0.137 (2)	0.5987 (5)	0.112 (4)
H10	0.5907	0.0956	0.6075	0.134*
C11	0.6896 (8)	0.313 (2)	0.6235 (5)	0.118 (4)
H11	0.6732	0.3910	0.6483	0.142*
C12	0.6030 (7)	−0.170 (2)	0.5337 (4)	0.103 (3)
C13	0.5286 (8)	−0.260 (2)	0.5499 (5)	0.122 (4)
H13A	0.4970	−0.3703	0.5269	0.183*
H13B	0.4956	−0.1182	0.5546	0.183*
H13C	0.5455	−0.3508	0.5786	0.183*
Hg1	1.0000	1.21208 (11)	0.7500	0.0886 (3)
N1	0.9161 (5)	0.9236 (15)	0.6984 (3)	0.080 (2)
O1	0.6156 (6)	−0.2498 (18)	0.4976 (4)	0.147 (4)

	U11	U22	U33	U12	U13	U23
Br1	0.1385 (11)	0.1556 (13)	0.1188 (11)	−0.0357 (9)	0.0583 (8)	0.0154 (9)
C1	0.106 (9)	0.126 (10)	0.128 (11)	−0.044 (7)	0.062 (8)	−0.044 (8)
C2	0.120 (7)	0.128 (7)	0.113 (7)	−0.019 (6)	0.059 (6)	−0.028 (6)
C3	0.070 (6)	0.082 (6)	0.058 (6)	0.002 (5)	0.021 (5)	0.011 (5)
C4	0.112 (7)	0.150 (8)	0.102 (7)	−0.031 (6)	0.042 (6)	−0.003 (6)
C5	0.108 (9)	0.175 (12)	0.085 (8)	−0.053 (9)	0.035 (7)	−0.031 (8)
C6	0.079 (6)	0.067 (6)	0.071 (6)	0.005 (5)	0.012 (5)	0.003 (5)
C7	0.100 (7)	0.146 (8)	0.130 (8)	−0.023 (6)	0.040 (6)	−0.036 (7)
C8	0.100 (9)	0.166 (12)	0.133 (11)	−0.033 (9)	0.044 (8)	−0.052 (10)
C9	0.086 (7)	0.077 (6)	0.070 (7)	0.000 (5)	0.008 (5)	0.006 (5)
C10	0.109 (9)	0.123 (9)	0.115 (10)	−0.035 (8)	0.049 (8)	−0.006 (8)
C11	0.119 (10)	0.131 (10)	0.113 (10)	−0.045 (8)	0.042 (8)	−0.048 (8)
C12	0.116 (9)	0.101 (8)	0.087 (8)	−0.008 (7)	0.008 (7)	−0.004 (7)
C13	0.130 (10)	0.121 (9)	0.111 (9)	−0.050 (8)	0.019 (7)	−0.006 (7)
Hg1	0.0841 (4)	0.1019 (5)	0.0846 (5)	0.000	0.0283 (3)	0.000
N1	0.071 (5)	0.096 (6)	0.074 (6)	−0.001 (4)	0.016 (4)	−0.007 (5)
O1	0.153 (8)	0.178 (9)	0.110 (7)	−0.043 (6)	0.031 (6)	−0.048 (6)

Br1—Hg1	2.4701 (14)	C8—C9	1.357 (14)
C1—N1	1.301 (13)	C8—H8	0.9300
C1—C2	1.381 (16)	C9—C10	1.346 (14)
C1—H1	0.9300	C9—C12	1.487 (14)
C2—C3	1.335 (13)	C10—C11	1.355 (16)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.336 (14)	C11—H11	0.9300
C3—C6	1.459 (12)	C12—O1	1.203 (14)
C4—C5	1.388 (16)	C12—C13	1.498 (17)
C4—H4	0.9300	C13—H13A	0.9600
C5—N1	1.282 (13)	C13—H13B	0.9600
C5—H5	0.9300	C13—H13C	0.9600
C6—C11	1.356 (14)	Hg1—N1	2.383 (8)
C6—C7	1.356 (15)	Hg1—N1i	2.383 (8)
C7—C8	1.364 (16)	Hg1—Br1i	2.4701 (14)
C7—H7	0.9300
N1—C1—C2	123.4 (10)	C8—C9—C12	120.8 (11)
N1—C1—H1	118.3	C9—C10—C11	122.0 (11)
C2—C1—H1	118.3	C9—C10—H10	119.0
C3—C2—C1	122.8 (11)	C11—C10—H10	119.0
C3—C2—H2	118.6	C10—C11—C6	122.7 (11)
C1—C2—H2	118.6	C10—C11—H11	118.6
C2—C3—C4	112.3 (10)	C6—C11—H11	118.6
C2—C3—C6	124.9 (9)	O1—C12—C9	121.4 (12)
C4—C3—C6	122.7 (9)	O1—C12—C13	118.9 (11)
C3—C4—C5	123.2 (11)	C9—C12—C13	119.6 (11)
C3—C4—H4	118.4	C12—C13—H13A	109.5
C5—C4—H4	118.4	C12—C13—H13B	109.5
N1—C5—C4	123.0 (11)	H13A—C13—H13B	109.5
N1—C5—H5	118.5	C12—C13—H13C	109.5
C4—C5—H5	118.5	H13A—C13—H13C	109.5
C11—C6—C7	114.5 (10)	H13B—C13—H13C	109.5
C11—C6—C3	121.0 (9)	N1—Hg1—N1i	100.3 (4)
C7—C6—C3	124.4 (10)	N1—Hg1—Br1	98.7 (2)
C6—C7—C8	123.6 (12)	N1i—Hg1—Br1	101.8 (2)
C6—C7—H7	118.2	N1—Hg1—Br1i	101.8 (2)
C8—C7—H7	118.2	N1i—Hg1—Br1i	98.7 (2)
C9—C8—C7	120.4 (12)	Br1—Hg1—Br1i	147.81 (9)
C9—C8—H8	119.8	C5—N1—C1	115.1 (9)
C7—C8—H8	119.8	C5—N1—Hg1	119.5 (7)
C10—C9—C8	116.7 (10)	C1—N1—Hg1	125.3 (7)
C10—C9—C12	122.5 (11)
N1—C1—C2—C3	−2(2)	C9—C10—C11—C6	−2(2)
C1—C2—C3—C4	−0.6 (19)	C7—C6—C11—C10	0(2)
C1—C2—C3—C6	−179.5 (12)	C3—C6—C11—C10	−178.3 (12)
C2—C3—C4—C5	4(2)	C10—C9—C12—O1	170.9 (13)
C6—C3—C4—C5	−177.4 (12)	C8—C9—C12—O1	−10.3 (18)
C3—C4—C5—N1	−5(2)	C10—C9—C12—C13	−7.3 (16)
C2—C3—C6—C11	−167.2 (12)	C8—C9—C12—C13	171.5 (12)
C4—C3—C6—C11	14.0 (16)	C4—C5—N1—C1	3(2)
C2—C3—C6—C7	14.3 (16)	C4—C5—N1—Hg1	−175.1 (11)
C4—C3—C6—C7	−164.5 (12)	C2—C1—N1—C5	1(2)
C11—C6—C7—C8	1(2)	C2—C1—N1—Hg1	178.0 (10)
C3—C6—C7—C8	179.1 (12)	N1i—Hg1—N1—C5	81.6 (9)
C6—C7—C8—C9	0(2)	Br1—Hg1—N1—C5	−174.7 (9)
C7—C8—C9—C10	−1(2)	Br1i—Hg1—N1—C5	−19.6 (9)
C7—C8—C9—C12	179.9 (12)	N1i—Hg1—N1—C1	−95.9 (10)
C8—C9—C10—C11	2(2)	Br1—Hg1—N1—C1	7.9 (10)
C12—C9—C10—C11	−179.1 (12)	Br1i—Hg1—N1—C1	162.9 (9)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···Br1ii	0.93	3.01	3.579 (13)	121

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯Br1i	0.93	3.01	3.579 (13)	121

Symmetry code: (i) .