[1,3-Bis(2-ethoxy-phen-yl)triazenido]bromidomercury(II).

To the central atom of the title compound, [HgBr(C(16)H(18)N(3)O(2))], is attached one bromide ion and a 1,3-bis-(2-ethoxy-phen-yl)triazenide ligand through one O and two N atoms, forming a distorted square-planar geometry around the Hg(II) atom. The mononuclear complexes are linked into centrosymmetric dimers by non-classical inter-molecular C-H⋯N hydrogen bonds and by weak Hg-η(3)-arene π-inter-actions [mean distance = 3.434 (3) Å]. The resulting dimeric units are assembled into zigzag chains by translation along the crystallographic c axis through secondary C-H⋯π edge-to-face benzene ring inter-actions.

Related literature

For aryl triazenes, their structural properties and metal complexes see: Vrieze & Van Koten (1987 ▶); Hörner et al. (2002 ▶, 2004 ▶, 2006 ▶). For the different coordination modes of the triazenide ligand, see: Moore & Robinson (1986 ▶). For the synthesis and mol­ecular structure of similar structures with cyano, meth­oxy and eth­oxy groups, see: Melardi et al. (2008 ▶); Rofouei et al. (2006 ▶); Rofouei, Melardi, Salemi et al. (2009 ▶). For the synthesis and crystal structures of HgII complexes with [1,3-bis­(2-methoxy­phen­yl)]triazene by using HgCl2, HgBr2, Hg(CH3COO)2 and Hg(SCN)2 salts as starting materials, see: Melardi et al. (2007 ▶); Hematyar & Rofouei (2008 ▶); Rofouei, Hematyar et al. (2009 ▶). For the synthesis and crystal structures of cadmium(II) and silver(I) complexes with 1,3-bis­(2-methoxy­phen­yl)triazene, see: Rofouei, Melardi, Khalili Ghaydari et al. (2009 ▶) and Payehghadr et al. (2007 ▶), respectively. For the synthesis and characterization of an isomorphous HgII structure with [1,3-bis­(2-ethoxy­phen­yl)]triazene by using HgCl2 instead of HgBr2, see: Melardi et al. (2009 ▶).

Experimental

Crystal data

[HgBr(C16H18N3O2)]

M = 564.83

Monoclinic,

a = 10.2359 (7) Å

b = 7.4659 (5) Å

c = 22.4123 (14) Å

β = 98.860 (6)°

V = 1692.32 (19) Å3

Z = 4

Mo Kα radiation

μ = 11.47 mm−1

T = 100 K

0.28 × 0.12 × 0.03 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ▶) T min = 0.221, T max = 0.709

20759 measured reflections

4943 independent reflections

4081 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.062

S = 1.00

4943 reflections

210 parameters

H-atom parameters constrained

Δρmax = 1.33 e Å−3

Δρmin = −1.43 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: Mercury (Macrae et al., 2006 ▶), PLATON (Spek, 2009 ▶) and SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809038732/om2271sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809038732/om2271Isup2.hkl

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

[HgBr(C16H18N3O2)]	F(000) = 1064
Mr = 564.83	Dx = 2.217 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4844 reflections
a = 10.2359 (7) Å	θ = 2.3–29.5°
b = 7.4659 (5) Å	µ = 11.47 mm−1
c = 22.4123 (14) Å	T = 100 K
β = 98.860 (6)°	Plate, orange
V = 1692.32 (19) Å3	0.28 × 0.12 × 0.03 mm
Z = 4

Bruker APEXII CCD diffractometer	4943 independent reflections
Radiation source: fine-focus sealed tube	4081 reflections with I > 2σ(I)
graphite	Rint = 0.061
ω scans	θmax = 30.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −14→14
Tmin = 0.221, Tmax = 0.709	k = −10→10
20759 measured reflections	l = −31→31

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.062	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.01P)2] where P = (Fo2 + 2Fc2)/3
4943 reflections	(Δ/σ)max = 0.001
210 parameters	Δρmax = 1.33 e Å−3
0 restraints	Δρmin = −1.43 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. The maximum and minimum difference map peaks are within 1.21 Å of Hg1.

	x	y	z	Uiso*/Ueq
Hg1	−0.152069 (14)	0.681795 (19)	0.053806 (7)	0.01739 (5)
Br1	−0.36007 (4)	0.63210 (6)	0.08813 (2)	0.02803 (10)
O1	−0.1764 (2)	0.8602 (3)	−0.05325 (12)	0.0160 (5)
O2	0.0190 (3)	0.4368 (3)	0.20087 (13)	0.0175 (6)
N1	0.0246 (3)	0.7115 (4)	0.01922 (15)	0.0148 (6)
N2	0.1262 (3)	0.6390 (4)	0.05569 (15)	0.0140 (6)
N3	0.0888 (3)	0.5769 (4)	0.10309 (15)	0.0147 (6)
C1	−0.0555 (3)	0.8727 (5)	−0.07197 (17)	0.0127 (7)
C2	0.0503 (4)	0.7918 (4)	−0.03385 (17)	0.0133 (7)
C3	0.1769 (4)	0.7992 (5)	−0.05036 (18)	0.0170 (8)
H3	0.2493	0.7441	−0.0254	0.020*
C4	0.1972 (4)	0.8862 (5)	−0.1028 (2)	0.0202 (8)
H4	0.2834	0.8906	−0.1136	0.024*
C5	0.0928 (4)	0.9665 (5)	−0.13943 (18)	0.0182 (8)
H5	0.1073	1.0270	−0.1751	0.022*
C6	−0.0331 (4)	0.9589 (5)	−0.12414 (18)	0.0168 (8)
H6	−0.1048	1.0134	−0.1497	0.020*
C7	0.1494 (3)	0.4203 (5)	0.19634 (18)	0.0143 (7)
C8	0.1896 (3)	0.4974 (5)	0.14479 (17)	0.0136 (7)
C9	0.3235 (4)	0.4931 (5)	0.13872 (18)	0.0172 (8)
H9	0.3514	0.5475	0.1045	0.021*
C10	0.4158 (4)	0.4114 (5)	0.18149 (19)	0.0187 (8)
H10	0.5066	0.4105	0.1770	0.022*
C11	0.3744 (4)	0.3301 (5)	0.23141 (19)	0.0183 (8)
H11	0.4371	0.2716	0.2606	0.022*
C12	0.2414 (4)	0.3343 (5)	0.23868 (19)	0.0173 (8)
H12	0.2139	0.2781	0.2727	0.021*
C13	−0.2862 (4)	0.9515 (5)	−0.08961 (18)	0.0174 (8)
H13A	−0.3002	0.9034	−0.1313	0.021*
H13B	−0.2678	1.0814	−0.0914	0.021*
C14	−0.4070 (4)	0.9196 (6)	−0.0602 (2)	0.0233 (9)
H14A	−0.4809	0.9907	−0.0809	0.035*
H14B	−0.3885	0.9552	−0.0177	0.035*
H14C	−0.4303	0.7922	−0.0630	0.035*
C15	−0.0256 (4)	0.3651 (5)	0.25327 (19)	0.0213 (8)
H15A	0.0251	0.4179	0.2902	0.026*
H15B	−0.0132	0.2336	0.2548	0.026*
C16	−0.1692 (4)	0.4104 (6)	0.2491 (2)	0.0272 (10)
H16A	−0.2048	0.3543	0.2828	0.041*
H16B	−0.2173	0.3659	0.2108	0.041*
H16C	−0.1795	0.5406	0.2511	0.041*

	U11	U22	U33	U12	U13	U23
Hg1	0.01495 (7)	0.01991 (8)	0.01826 (8)	−0.00083 (5)	0.00561 (5)	0.00169 (6)
Br1	0.01972 (19)	0.0300 (2)	0.0374 (3)	0.00079 (16)	0.01402 (18)	0.00757 (19)
O1	0.0130 (12)	0.0221 (13)	0.0132 (14)	0.0018 (10)	0.0027 (10)	0.0021 (11)
O2	0.0165 (13)	0.0211 (13)	0.0156 (14)	−0.0003 (10)	0.0042 (11)	0.0040 (11)
N1	0.0134 (14)	0.0167 (15)	0.0134 (16)	0.0014 (11)	−0.0006 (12)	0.0011 (12)
N2	0.0169 (15)	0.0129 (14)	0.0117 (16)	−0.0016 (11)	0.0006 (12)	−0.0013 (12)
N3	0.0156 (15)	0.0143 (14)	0.0138 (16)	−0.0030 (11)	0.0010 (12)	0.0007 (12)
C1	0.0149 (17)	0.0127 (15)	0.0103 (17)	−0.0005 (13)	0.0017 (14)	−0.0027 (14)
C2	0.0158 (17)	0.0123 (16)	0.0123 (18)	−0.0007 (12)	0.0043 (14)	−0.0009 (13)
C3	0.0142 (17)	0.0181 (18)	0.019 (2)	−0.0015 (13)	0.0032 (15)	0.0000 (15)
C4	0.0159 (18)	0.0242 (19)	0.022 (2)	−0.0039 (15)	0.0085 (16)	−0.0017 (17)
C5	0.0197 (19)	0.0212 (19)	0.0149 (19)	−0.0034 (15)	0.0061 (15)	0.0005 (16)
C6	0.0183 (18)	0.0148 (17)	0.017 (2)	−0.0002 (14)	0.0017 (15)	0.0008 (15)
C7	0.0141 (17)	0.0119 (16)	0.0168 (19)	0.0004 (13)	0.0028 (14)	0.0005 (14)
C8	0.0170 (17)	0.0123 (16)	0.0110 (18)	0.0001 (13)	0.0007 (14)	−0.0020 (14)
C9	0.0208 (19)	0.0146 (17)	0.017 (2)	−0.0034 (14)	0.0041 (15)	−0.0011 (15)
C10	0.0171 (18)	0.0187 (19)	0.019 (2)	−0.0005 (14)	−0.0001 (15)	−0.0015 (16)
C11	0.0183 (18)	0.0173 (17)	0.017 (2)	0.0004 (14)	−0.0035 (15)	−0.0022 (16)
C12	0.0215 (18)	0.0131 (17)	0.0167 (19)	−0.0001 (14)	0.0018 (15)	−0.0004 (15)
C13	0.0146 (17)	0.0189 (18)	0.017 (2)	−0.0005 (14)	−0.0018 (15)	0.0005 (16)
C14	0.0162 (19)	0.030 (2)	0.023 (2)	0.0012 (16)	0.0029 (16)	−0.0019 (18)
C15	0.029 (2)	0.0205 (19)	0.015 (2)	0.0008 (16)	0.0069 (17)	0.0025 (16)
C16	0.029 (2)	0.029 (2)	0.028 (3)	0.0044 (17)	0.0154 (19)	0.0074 (19)

Hg1—N1	2.086 (3)	C7—C8	1.408 (5)
Hg1—Br1	2.4014 (4)	C8—C9	1.398 (5)
Hg1—N3	2.660 (3)	C9—C10	1.380 (5)
O1—C1	1.370 (4)	C9—H9	0.9500
O1—C13	1.452 (4)	C10—C11	1.395 (6)
O2—C7	1.359 (4)	C10—H10	0.9500
O2—C15	1.428 (5)	C11—C12	1.396 (5)
N1—N2	1.334 (4)	C11—H11	0.9500
N1—C2	1.393 (5)	C12—H12	0.9500
N2—N3	1.271 (4)	C13—C14	1.507 (5)
N3—C8	1.412 (5)	C13—H13A	0.9900
C1—C6	1.384 (5)	C13—H13B	0.9900
C1—C2	1.408 (5)	C14—H14A	0.9800
C2—C3	1.403 (5)	C14—H14B	0.9800
C3—C4	1.386 (6)	C14—H14C	0.9800
C3—H3	0.9500	C15—C16	1.497 (6)
C4—C5	1.381 (6)	C15—H15A	0.9900
C4—H4	0.9500	C15—H15B	0.9900
C5—C6	1.385 (5)	C16—H16A	0.9800
C5—H5	0.9500	C16—H16B	0.9800
C6—H6	0.9500	C16—H16C	0.9800
C7—C12	1.387 (5)
N1—Hg1—Br1	175.94 (9)	C10—C9—C8	121.3 (4)
N1—Hg1—N3	52.01 (11)	C10—C9—H9	119.4
Br1—Hg1—N3	129.22 (7)	C8—C9—H9	119.4
C1—O1—C13	117.0 (3)	C9—C10—C11	119.3 (4)
C7—O2—C15	118.0 (3)	C9—C10—H10	120.4
N2—N1—C2	117.8 (3)	C11—C10—H10	120.4
N2—N1—Hg1	111.6 (2)	C10—C11—C12	120.4 (4)
C2—N1—Hg1	130.7 (2)	C10—C11—H11	119.8
N3—N2—N1	110.7 (3)	C12—C11—H11	119.8
N2—N3—C8	115.1 (3)	C7—C12—C11	120.1 (4)
N2—N3—Hg1	85.7 (2)	C7—C12—H12	119.9
C8—N3—Hg1	159.2 (3)	C11—C12—H12	119.9
O1—C1—C6	124.4 (3)	O1—C13—C14	107.3 (3)
O1—C1—C2	115.6 (3)	O1—C13—H13A	110.3
C6—C1—C2	120.0 (3)	C14—C13—H13A	110.3
N1—C2—C3	123.1 (3)	O1—C13—H13B	110.3
N1—C2—C1	118.3 (3)	C14—C13—H13B	110.3
C3—C2—C1	118.6 (3)	H13A—C13—H13B	108.5
C4—C3—C2	120.5 (4)	C13—C14—H14A	109.5
C4—C3—H3	119.7	C13—C14—H14B	109.5
C2—C3—H3	119.7	H14A—C14—H14B	109.5
C5—C4—C3	120.3 (4)	C13—C14—H14C	109.5
C5—C4—H4	119.9	H14A—C14—H14C	109.5
C3—C4—H4	119.9	H14B—C14—H14C	109.5
C4—C5—C6	120.0 (4)	O2—C15—C16	107.5 (3)
C4—C5—H5	120.0	O2—C15—H15A	110.2
C6—C5—H5	120.0	C16—C15—H15A	110.2
C1—C6—C5	120.6 (4)	O2—C15—H15B	110.2
C1—C6—H6	119.7	C16—C15—H15B	110.2
C5—C6—H6	119.7	H15A—C15—H15B	108.5
O2—C7—C12	124.2 (4)	C15—C16—H16A	109.5
O2—C7—C8	116.0 (3)	C15—C16—H16B	109.5
C12—C7—C8	119.8 (3)	H16A—C16—H16B	109.5
C9—C8—C7	119.0 (3)	C15—C16—H16C	109.5
C9—C8—N3	124.9 (3)	H16A—C16—H16C	109.5
C7—C8—N3	116.0 (3)	H16B—C16—H16C	109.5
N3—Hg1—N1—N2	1.4 (2)	C3—C4—C5—C6	−0.6 (6)
N3—Hg1—N1—C2	−178.7 (4)	O1—C1—C6—C5	179.5 (3)
C2—N1—N2—N3	177.6 (3)	C2—C1—C6—C5	0.1 (5)
Hg1—N1—N2—N3	−2.5 (3)	C4—C5—C6—C1	0.6 (6)
N1—N2—N3—C8	−179.9 (3)	C15—O2—C7—C12	1.7 (5)
N1—N2—N3—Hg1	1.8 (3)	C15—O2—C7—C8	−178.3 (3)
N1—Hg1—N3—N2	−1.37 (19)	O2—C7—C8—C9	176.9 (3)
Br1—Hg1—N3—N2	173.68 (16)	C12—C7—C8—C9	−3.1 (5)
N1—Hg1—N3—C8	−177.1 (7)	O2—C7—C8—N3	−2.1 (5)
Br1—Hg1—N3—C8	−2.1 (7)	C12—C7—C8—N3	177.9 (3)
C13—O1—C1—C6	−3.0 (5)	N2—N3—C8—C9	3.9 (5)
C13—O1—C1—C2	176.4 (3)	Hg1—N3—C8—C9	179.2 (5)
N2—N1—C2—C3	0.1 (5)	N2—N3—C8—C7	−177.2 (3)
Hg1—N1—C2—C3	−179.7 (3)	Hg1—N3—C8—C7	−1.9 (8)
N2—N1—C2—C1	−178.4 (3)	C7—C8—C9—C10	1.5 (5)
Hg1—N1—C2—C1	1.7 (5)	N3—C8—C9—C10	−179.6 (3)
O1—C1—C2—N1	−1.5 (5)	C8—C9—C10—C11	0.6 (6)
C6—C1—C2—N1	177.9 (3)	C9—C10—C11—C12	−1.2 (6)
O1—C1—C2—C3	179.8 (3)	O2—C7—C12—C11	−177.5 (3)
C6—C1—C2—C3	−0.7 (5)	C8—C7—C12—C11	2.5 (5)
N1—C2—C3—C4	−177.8 (3)	C10—C11—C12—C7	−0.3 (6)
C1—C2—C3—C4	0.7 (5)	C1—O1—C13—C14	−179.7 (3)
C2—C3—C4—C5	−0.1 (6)	C7—O2—C15—C16	176.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13B···N2i	0.99	2.60	3.496 (5)	151
C12—H12···Cg1ii	0.95	2.85	3.559 (4)	132
C13—H13A···Cg1iii	0.99	2.72	3.523 (4)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13B⋯N2i	0.99	2.60	3.496 (5)	151
C12—H12⋯Cg1ii	0.95	2.85	3.559 (4)	132
C13—H13A⋯Cg1iii	0.99	2.72	3.523 (4)	139

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 is the centroid of the C7–C12 aromatic ring.