Bis[4-amino-N-(4-methyl­pyrimidin-2-yl-κN3)benzene­sulfonamidato-κN](2,2′-bi­pyridine-κ2N,N′)mercury(II)

Hossain, G.M.G.; Amoroso, A.J.

doi:10.1107/S1600536814004760

metal-organic compounds

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ISSN: 2056-9890

Volume 70| Part 4| April 2014| Pages m127-m128

doi:10.1107/S1600536814004760

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Bis[4-amino-N-(4-methylpyrimidin-2-yl-κN³)benzenesulfonamidato-κN](2,2′-bipyridine-κ²N,N′)mercury(II)

G. M. Golzar Hossain ^a ^* and A. J. Amoroso ^b

^aDepartment of Chemistry, University of Dhaka, Dhaka 1000, Bangladesh, and ^bSchool of Chemistry, Cardiff University, Cardiff CF10 3AT, Wales
^*Correspondence e-mail: acsbd@yahoo.com

(Received 24 February 2014; accepted 2 March 2014; online 8 March 2014)

The complete molecule 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 tetrahedral (from the N,N′-bidenate bipyridine molecule 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 molecules into a three-dimensional network.

CCDC reference: 989386

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_r = 883.37
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.039
wR(F²) = 0.074
S = 1.10
3874 reflections
231 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.13 e Å⁻³
Δρ_min = −0.75 e Å⁻³

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) $[x, -y+1, z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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).

Supporting information

CCDC reference: 989386

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536814004760/hb7201sup1.cif

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

checkCIF report

Comment top

The mercury complexes of some related ligands have been reported (Garcia-Raso et al., 1997; Hossain et al., 2007). In the title complex, sulfamerazine behaves as a bidentate anionic ligand and Hg(II) ion is coordinated via sulfonamidic N(11) and pyrimido N(12) atoms, the fifth and sixth coordination sites are occupied by bipyridine molecule. The geometry of the complex is trigonal prismatic with the Hg atom lying on a twofold axis as the bpy molecule lies on the one part and the two larger sulfamerazine molecules lie on the other part.

The Hg–N(11) bond distance of 2.216 (3) Å is slightly longer than the values of 2.087 (4) Å (Garcia-Raso et al., 1997), 2.071 (4) Å (Garcia-Raso et al., 2000) and 2.14 (2) Å (Saladini et al., 2001). The pyrimido nitrogen [N(12)] atom makes bond with longer interaction with the distance of 2.881 (3) Å. The C(18)—N(14) bond distance of 1.373 (5) Å is in good agreement with the corresponding bond in free sulfamerazine suggesting the terminal amino group is not coordinated with the Hg atoms. The Hg—N(1) bond distance of 2.323 (3) Å is longer than the corresponding bond lengths of 2.140 (3) and 2.124 (3) Å (Zamora et al., 1982) and 2.130 Å (Hergold-Brundić et al., 1989).

The bond angles around the S atom correspond to a distorted tetrahedral geometry. The bond distance C(18)—N(14) (Terminal amino group) of 1.371 (5) Å and the torsion angle C(15)—S(11)—N(11)—C(11) of 74.4 (4)° are larger than those observed in the related structures (Hossain & Amoroso, 2007; Hossain & Amoroso, 2012). The dihedral angle between the aromatic rings of the sulfamerazinate anion of 73.27 (13)° is larger than the value of 71.10 (14)° (Hossain & Amoroso, 2007) and smaller than the value of 76.60 (8)° (Hossain & Amoroso, 2012) in the sulfadiazinate anion.

The packing of the complex unit (Fig. 2) is governed by weak (intermolecular N—H···N, and N—H···O) hydrogen bonds (Table 2) between the amino (–NH2) group of one complex unit and the sulfonyl oxygen and the pyrimido nitrogen atoms of the next units.

Related literature top

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 top

The complex was obtained by dissolving (2.723 g, 2 mmol) sulfamerazine in 50 ml of methanol followed by drop-wise addition of Hg(CH₃COO)₂·4H₂O (1.245 g, 1 mmol) in water with constant stirring on hot plate for 1 h. A white precipitate was formed, filtered and washed with methanol and dried in a desiccator over silica gel. The precipitate was dissolved in DMF, bipyri dine (0.235 g, 1 mmol) was added to this solution and stirred for 30 minutes. The solution was filtered and left for crystallization. A week later, colourless blocks were obtained.

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); 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).

Figures top

	Fig. 1. The molecular structure of (I), with 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The packing of (I), viewed down the a-axis, showing one layer of molecules connected by N—H···N and N—H···O hydrogen bonds (dashed lines).

Bis[4-amino-N-(4-methylpyrimidin-2-yl-κN³)benzenesulfonamidato-κN](2,2'-bipyridine-κ²N,N')mercury(II) top

Crystal data top

[Hg(C₁₁H₁₁N₄O₂S)₂(C₁₀H₈N₂)]	F(000) = 1744
M_r = 883.37	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0108P)² + 13.7149P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max < 0.001
3874 reflections	Δρ_max = 1.13 e Å⁻³
231 parameters	Δρ_min = −0.75 e Å⁻³

Crystal data top

[Hg(C₁₁H₁₁N₄O₂S)₂(C₁₀H₈N₂)]	V = 3371.4 (3) Å³
M_r = 883.37	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 18.7483 (8) Å	µ = 4.74 mm⁻¹
b = 15.0824 (7) Å	T = 150 K
c = 12.1143 (6) Å	0.12 × 0.12 × 0.10 mm
β = 100.202 (2)°

Data collection top

Nonius KappaCCD diffractometer	3874 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1995)]	3408 reflections with I > 2σ(I)
T_min = 0.600, T_max = 0.648	R_int = 0.072
29910 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	3 restraints
wR(F²) = 0.074	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.0108P)² + 13.7149P] where P = (F_o² + 2F_c²)/3
3874 reflections	Δρ_max = 1.13 e Å⁻³
231 parameters	Δρ_min = −0.75 e Å⁻³

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

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)

Symmetry codes: (ii) x, −y+1, z+1/2; (iii) −x+1/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Hg(C₁₁H₁₁N₄O₂S)₂(C₁₀H₈N₂)]
M_r	883.37
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	150
a, b, c (Å)	18.7483 (8), 15.0824 (7), 12.1143 (6)
β (°)	100.202 (2)
V (Å³)	3371.4 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.74
Crystal size (mm)	0.12 × 0.12 × 0.10

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1995)]
T_min, T_max	0.600, 0.648
No. of measured, independent and observed [I > 2σ(I)] reflections	29910, 3874, 3408
R_int	0.072
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.074, 1.10
No. of reflections	3874
No. of parameters	231
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
	w = 1/[σ²(F_o²) + (0.0108P)² + 13.7149P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	1.13, −0.75

Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), SHELXS97 (Sheldrick, 2008), SHELXL2013 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012).

Selected bond lengths (Å) top

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N14—H14A···O11ⁱ	0.900 (3)	2.41 (3)	3.173 (5)	143 (4)
N14—H14A···N13ⁱ	0.900 (3)	2.42 (3)	3.125 (6)	135 (4)
N14—H14B···O11ⁱⁱ	0.900 (3)	2.125 (14)	2.997 (5)	163 (4)

Symmetry codes: (i) x, −y+1, z+1/2; (ii) −x+1/2, y+1/2, −z+1/2.

Acknowledgements

GMGH is grateful to the Ministry of Science and Technology, Bangladesh, for financial support and to School of Chemistry, Cardiff University, Wales, for the crystallographic services.

References

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