Bis[4-amino-N-(4-methyl-pyrimidin-2-yl-κN (3))benzene-sulfonamidato-κN](2,2'-bi-pyridine-κ(2) N,N')mercury(II).

The complete mol-ecule of the title complex, [Hg(C11H11N4O2S)2(C10H8N2)], is generated by crystallographic twofold symmetry, with the mercury cation lying on the rotation axis. The mercury coordination polyhedron can be described as tetra-hedral (from the N,N'-bidenate bi-pyridine mol-ecule and the sulfonamide N atoms of the sulfamerazine anions) or as squashed trigonal-prismatic, if two long (> 2.80 Å) Hg-N bonds to pyrimidine N atoms are included. The dihedral angle between the aromatic rings in the anion is 73.3 (2)°. In the crystal, N-H⋯(N,O) and N-H⋯N hydrogen bonds link the mol-ecules into a three-dimensional network.

Related literature

For related structures, see: Garcia-Raso et al. (1997 ▶, 2000 ▶); Saladini et al. (2001 ▶); Zamora et al. (1982 ▶); Hergold-Brundić et al. (1989 ▶). For ligand conformations, see: Hossain & Amoroso (2007 ▶, 2012 ▶); Hossain et al. (2007 ▶).

Experimental

Crystal data

[Hg(C11H11N4O2S)2(C10H8N2)]

M = 883.37

Monoclinic,

a = 18.7483 (8) Å

b = 15.0824 (7) Å

c = 12.1143 (6) Å

β = 100.202 (2)°

V = 3371.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 4.74 mm−1

T = 150 K

0.12 × 0.12 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1995 ▶)] T min = 0.600, T max = 0.648

29910 measured reflections

3874 independent reflections

3408 reflections with I > 2σ(I)

R int = 0.072

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.074

S = 1.10

3874 reflections

231 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.13 e Å−3

Δρmin = −0.75 e Å−3

Data collection: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT (Hooft, 1998 ▶); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814004760/hb7201sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814004760/hb7201Isup2.hkl

CCDC reference: 989386

Additional supporting information: crystallographic information; 3D view; checkCIF report

[Hg(C11H11N4O2S)2(C10H8N2)]	F(000) = 1744
Mr = 883.37	Dx = 1.740 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 18.7483 (8) Å	Cell parameters from 3874 reflections
b = 15.0824 (7) Å	θ = 2.9–27.5°
c = 12.1143 (6) Å	µ = 4.74 mm−1
β = 100.202 (2)°	T = 150 K
V = 3371.4 (3) Å3	Block, colorless
Z = 4	0.12 × 0.12 × 0.10 mm

Nonius KappaCCD diffractometer	3408 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.072
ω scans	θmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan (SORTAV; Blessing, 1995)]	h = −24→24
Tmin = 0.600, Tmax = 0.648	k = −19→19
29910 measured reflections	l = −15→15
3874 independent reflections

Refinement on F2	3 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.074	w = 1/[σ2(Fo2) + (0.0108P)2 + 13.7149P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
3874 reflections	Δρmax = 1.13 e Å−3
231 parameters	Δρmin = −0.75 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.

	x	y	z	Uiso*/Ueq
Hg1	0.0000	0.15586 (2)	0.2500	0.02712 (9)
S11	0.14988 (6)	0.26641 (7)	0.20322 (9)	0.0241 (2)
O11	0.19225 (16)	0.26047 (19)	0.1139 (2)	0.0300 (7)
O12	0.17100 (16)	0.20881 (18)	0.2977 (2)	0.0298 (7)
N11	0.0655 (2)	0.2427 (2)	0.1595 (3)	0.0250 (8)
N12	−0.0384 (2)	0.2333 (2)	0.0300 (3)	0.0272 (8)
N13	0.0520 (2)	0.3400 (2)	0.0030 (3)	0.0321 (9)
N14	0.1869 (2)	0.6308 (2)	0.3883 (3)	0.0297 (9)
C11	0.0260 (2)	0.2745 (3)	0.0597 (3)	0.0236 (9)
C12	−0.0808 (2)	0.2607 (3)	−0.0646 (4)	0.0316 (10)
C13	−0.0589 (3)	0.3277 (3)	−0.1283 (4)	0.0382 (12)
H13	−0.0889	0.3474	−0.1954	0.046*
C14	0.0076 (3)	0.3648 (3)	−0.0915 (4)	0.0390 (12)
H14	0.0233	0.4107	−0.1353	0.047*
C15	0.1581 (2)	0.3761 (3)	0.2533 (3)	0.0228 (9)
C16	0.1290 (3)	0.3989 (3)	0.3461 (4)	0.0304 (10)
H16	0.1012	0.3566	0.3783	0.036*
C17	0.1398 (3)	0.4825 (3)	0.3930 (4)	0.0292 (10)
H17	0.1204	0.4965	0.4581	0.035*
C18	0.1790 (2)	0.5466 (3)	0.3453 (3)	0.0254 (9)
C19	0.2096 (2)	0.5225 (3)	0.2518 (4)	0.0290 (10)
H19	0.2379	0.5644	0.2197	0.035*
C20	0.1989 (2)	0.4381 (3)	0.2058 (4)	0.0289 (10)
H20	0.2193	0.4226	0.1421	0.035*
C21	−0.1540 (3)	0.2183 (4)	−0.0972 (5)	0.0514 (15)
H21A	−0.1481	0.1554	−0.1135	0.077*
H21B	−0.1807	0.2478	−0.1641	0.077*
H21C	−0.1811	0.2241	−0.0354	0.077*
N1	−0.0594 (2)	0.0298 (2)	0.1713 (3)	0.0302 (8)
C1	−0.0330 (2)	−0.0493 (3)	0.2060 (3)	0.0275 (10)
C2	−0.0665 (3)	−0.1265 (3)	0.1612 (4)	0.0381 (12)
H2	−0.0474	−0.1826	0.1872	0.046*
C3	−0.1274 (3)	−0.1219 (3)	0.0792 (4)	0.0435 (13)
H3	−0.1510	−0.1744	0.0485	0.052*
C4	−0.1535 (3)	−0.0397 (3)	0.0424 (4)	0.0423 (12)
H4	−0.1944	−0.0344	−0.0160	0.051*
C5	−0.1189 (3)	0.0351 (3)	0.0922 (4)	0.0400 (12)
H5	−0.1379	0.0919	0.0696	0.048*
H14A	0.171 (2)	0.644 (3)	0.452 (2)	0.038 (14)*
H14B	0.2224 (18)	0.666 (2)	0.373 (4)	0.040 (14)*

	U11	U22	U33	U12	U13	U23
Hg1	0.02493 (15)	0.02381 (12)	0.02946 (13)	0.000	−0.00387 (9)	0.000
S11	0.0190 (6)	0.0238 (5)	0.0276 (5)	0.0009 (4)	−0.0009 (4)	−0.0021 (4)
O11	0.0231 (18)	0.0329 (16)	0.0338 (16)	−0.0007 (13)	0.0046 (14)	−0.0080 (14)
O12	0.0218 (17)	0.0271 (15)	0.0366 (17)	0.0026 (13)	−0.0053 (14)	0.0021 (13)
N11	0.025 (2)	0.0279 (18)	0.0192 (16)	0.0003 (15)	−0.0048 (15)	−0.0001 (15)
N12	0.017 (2)	0.0334 (19)	0.0283 (19)	0.0025 (15)	−0.0028 (15)	−0.0003 (16)
N13	0.025 (2)	0.039 (2)	0.0312 (19)	−0.0006 (18)	0.0009 (16)	0.0055 (18)
N14	0.030 (2)	0.0259 (19)	0.033 (2)	−0.0040 (16)	0.0056 (18)	−0.0031 (16)
C11	0.017 (2)	0.028 (2)	0.025 (2)	0.0039 (17)	0.0028 (17)	−0.0006 (18)
C12	0.018 (2)	0.041 (3)	0.033 (2)	0.0021 (19)	−0.0034 (19)	−0.002 (2)
C13	0.027 (3)	0.053 (3)	0.032 (2)	0.004 (2)	−0.004 (2)	0.006 (2)
C14	0.031 (3)	0.049 (3)	0.034 (3)	0.002 (2)	0.002 (2)	0.014 (2)
C15	0.018 (2)	0.0217 (19)	0.026 (2)	−0.0015 (16)	−0.0024 (17)	−0.0016 (17)
C16	0.028 (3)	0.031 (2)	0.034 (2)	−0.0052 (19)	0.010 (2)	0.002 (2)
C17	0.033 (3)	0.031 (2)	0.026 (2)	−0.0009 (19)	0.011 (2)	−0.0022 (19)
C18	0.017 (2)	0.030 (2)	0.026 (2)	−0.0009 (17)	−0.0057 (17)	0.0007 (18)
C19	0.026 (3)	0.028 (2)	0.033 (2)	−0.0038 (19)	0.006 (2)	0.0015 (19)
C20	0.026 (3)	0.032 (2)	0.029 (2)	−0.0007 (19)	0.0073 (19)	−0.0029 (19)
C21	0.023 (3)	0.076 (4)	0.047 (3)	−0.005 (3)	−0.014 (2)	0.020 (3)
N1	0.027 (2)	0.0289 (18)	0.0315 (19)	−0.0013 (16)	−0.0045 (17)	−0.0004 (16)
C1	0.025 (3)	0.030 (2)	0.028 (2)	0.0036 (18)	0.0033 (19)	0.0007 (19)
C2	0.042 (3)	0.025 (2)	0.046 (3)	−0.001 (2)	0.001 (2)	−0.007 (2)
C3	0.043 (3)	0.036 (3)	0.048 (3)	−0.009 (2)	−0.002 (3)	−0.015 (2)
C4	0.035 (3)	0.046 (3)	0.039 (3)	−0.008 (2)	−0.011 (2)	−0.010 (2)
C5	0.034 (3)	0.037 (3)	0.044 (3)	0.002 (2)	−0.010 (2)	0.001 (2)

Hg1—N11	2.214 (4)	C15—C20	1.394 (6)
Hg1—N11i	2.214 (4)	C16—C17	1.383 (6)
Hg1—N1	2.322 (3)	C16—H16	0.9500
Hg1—N1i	2.322 (3)	C17—C18	1.400 (6)
Hg1—N12i	2.883 (3)	C17—H17	0.9500
Hg1—N12	2.883 (3)	C18—C19	1.405 (6)
S11—O12	1.436 (3)	C19—C20	1.390 (6)
S11—O11	1.454 (3)	C19—H19	0.9500
S11—N11	1.616 (4)	C20—H20	0.9500
S11—C15	1.760 (4)	C21—H21A	0.9800
N11—C11	1.387 (5)	C21—H21B	0.9800
N12—C12	1.339 (5)	C21—H21C	0.9800
N12—C11	1.349 (5)	N1—C1	1.331 (5)
N13—C11	1.343 (6)	N1—C5	1.337 (6)
N13—C14	1.344 (6)	C1—C2	1.387 (6)
N14—C18	1.371 (5)	C1—C1i	1.483 (9)
N14—H14A	0.900 (3)	C2—C3	1.376 (7)
N14—H14B	0.900 (3)	C2—H2	0.9500
C12—C13	1.378 (7)	C3—C4	1.378 (7)
C12—C21	1.503 (7)	C3—H3	0.9500
C13—C14	1.367 (7)	C4—C5	1.386 (6)
C13—H13	0.9500	C4—H4	0.9500
C14—H14	0.9500	C5—H5	0.9500
C15—C16	1.378 (6)
N11—Hg1—N11i	107.50 (18)	C16—C15—C20	119.7 (4)
N11—Hg1—N1	123.31 (12)	C16—C15—S11	119.5 (3)
N11i—Hg1—N1	114.81 (13)	C20—C15—S11	120.6 (3)
N11—Hg1—N1i	114.81 (13)	C15—C16—C17	120.8 (4)
N11i—Hg1—N1i	123.31 (12)	C15—C16—H16	119.6
N1—Hg1—N1i	70.00 (17)	C17—C16—H16	119.6
N11—Hg1—N12i	98.53 (11)	C16—C17—C18	120.7 (4)
N11i—Hg1—N12i	51.11 (11)	C16—C17—H17	119.7
N1—Hg1—N12i	137.29 (11)	C18—C17—H17	119.7
N1i—Hg1—N12i	85.95 (11)	N14—C18—C17	120.8 (4)
N11—Hg1—N12	51.11 (11)	N14—C18—C19	120.9 (4)
N11i—Hg1—N12	98.53 (11)	C17—C18—C19	118.3 (4)
N1—Hg1—N12	85.95 (11)	C20—C19—C18	120.6 (4)
N1i—Hg1—N12	137.29 (11)	C20—C19—H19	119.7
N12i—Hg1—N12	132.17 (14)	C18—C19—H19	119.7
O12—S11—O11	116.49 (18)	C19—C20—C15	120.0 (4)
O12—S11—N11	104.05 (18)	C19—C20—H20	120.0
O11—S11—N11	111.99 (18)	C15—C20—H20	120.0
O12—S11—C15	107.41 (18)	C12—C21—H21A	109.5
O11—S11—C15	106.76 (19)	C12—C21—H21B	109.5
N11—S11—C15	110.01 (19)	H21A—C21—H21B	109.5
C11—N11—S11	123.3 (3)	C12—C21—H21C	109.5
C11—N11—Hg1	112.3 (3)	H21A—C21—H21C	109.5
S11—N11—Hg1	124.42 (18)	H21B—C21—H21C	109.5
C12—N12—C11	117.0 (4)	C1—N1—C5	119.8 (4)
C12—N12—Hg1	158.4 (3)	C1—N1—Hg1	118.7 (3)
C11—N12—Hg1	82.8 (2)	C5—N1—Hg1	121.6 (3)
C11—N13—C14	114.5 (4)	N1—C1—C2	120.7 (4)
C18—N14—H14A	120 (3)	N1—C1—C1i	116.3 (2)
C18—N14—H14B	120 (3)	C2—C1—C1i	122.9 (3)
H14A—N14—H14B	115 (3)	C3—C2—C1	120.0 (4)
N13—C11—N12	126.2 (4)	C3—C2—H2	120.0
N13—C11—N11	121.0 (4)	C1—C2—H2	120.0
N12—C11—N11	112.8 (4)	C2—C3—C4	118.8 (4)
N12—C12—C13	121.0 (4)	C2—C3—H3	120.6
N12—C12—C21	118.1 (4)	C4—C3—H3	120.6
C13—C12—C21	120.9 (4)	C3—C4—C5	118.6 (4)
C14—C13—C12	117.6 (4)	C3—C4—H4	120.7
C14—C13—H13	121.2	C5—C4—H4	120.7
C12—C13—H13	121.2	N1—C5—C4	122.0 (4)
N13—C14—C13	123.8 (5)	N1—C5—H5	119.0
N13—C14—H14	118.1	C4—C5—H5	119.0
C13—C14—H14	118.1

D—H···A	D—H	H···A	D···A	D—H···A
N14—H14A···O11ii	0.90 (1)	2.41 (3)	3.173 (5)	143 (4)
N14—H14A···N13ii	0.90 (1)	2.42 (3)	3.125 (6)	135 (4)
N14—H14B···O11iii	0.90 (1)	2.13 (1)	2.997 (5)	163 (4)

Table 1

Selected bond lengths (Å)

Hg1—N11	2.214 (4)
Hg1—N1	2.322 (3)
Hg1—N12	2.883 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N14—H14A⋯O11i	0.90 (1)	2.41 (3)	3.173 (5)	143 (4)
N14—H14A⋯N13i	0.90 (1)	2.42 (3)	3.125 (6)	135 (4)
N14—H14B⋯O11ii	0.90 (1)	2.13 (1)	2.997 (5)	163 (4)

Symmetry codes: (i) ; (ii) .