Literature DB >> 23795009

Bis[μ-2,5-bis-(pyridin-2-yl)-1,3,4-thia-diazole-κ(4) N (2),N (3):N (4),N (5)]bis-[(nitrato-κO)silver(I)] tetra-hydrate.

Abdelhakim Laachir1, Fouad Bentiss, Salaheddine Guesmi, Mohamed Saadi, Lahcen El Ammari.   

Abstract

The self-assembly of an angular 2,5-bis-(pyridin-2-yl)-1,3,4-thia-diazole ligand (L) with n class="Chemical">silver nitrate (AgNO3) produced a new dinuclear silver(I) coordination complex, [Ag2(C12H8N4S)2(NO3)2]·4H2O, which crystallizes with two Ag atoms bridged by two L ligands. The Ag atom is surrounded by four N atoms of L and by one O from the nitrate anion defining a distorted square pyramid. The atoms comprising the dication are nearly coplanar, with an r.m.s. deviation of 0.1997 Å. Mol-ecules are linked by C-H⋯O and O-H⋯O hydrogen bonds through nitrate anions and water mol-ecules, forming a two-dimensional porous network. The overall structure involves stacking of Ag complex layers along the b axis. The cohesion in the three-dimensional architecture is ensured by O⋯Ag inter-actions.

Entities:  

Year:  2013        PMID： 23795009      PMCID： PMC3684907          DOI： 10.1107/S1600536813014578

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For the synthesis of the ligand, see: Lebrini et al. (2005 ▶). For background to coordination polymers, see: Brammer (2004 ▶); Ghosh et al. (2004 ▶); Maspoch et al. (2004 ▶). For complexes with the same ligand but with other n class="Chemical">metals and counter-anions, see: Bentiss et al. (2012 ▶); Niu et al. (2009 ▶).

Experimental

Crystal data

[Ag2(C12H8N4S)2(n class="Chemical">NO3)2]·4H2O M = 892.41 Triclinic, a = 5.4251 (1) Å b = 10.6894 (3) Å c = 14.5865 (3) Å α = 108.910 (1)° β = 91.447 (1)° γ = 102.440 (1)° V = 777.30 (3) Å3 Z = 1 Mo Kα radiation μ = 1.47 mm−1 T = 296 K 0.42 × 0.32 × 0.23 mm

Data collection

Bruker X8 APEX diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ▶) T min = 0.739, T max = 0.867 29938 measured reflections 5388 independent reflections 3919 reflections with I > 2σ(I) R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.034 wR(F 2) = 0.090 S = 1.01 5388 reflections 217 parameters H-atom parameters constrained Δρmax = 0.92 e Å−3 Δρmin = −0.93 e Å−3 Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: PLATOn class="Chemical">N (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶). Click here for additional data file. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813014578/tk5229sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813014578/tk5229Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Ag2(C12H8N4S)2(NO3)2]·4H2OZ = 1
Mr = 892.41F(000) = 444
Triclinic, P1Dx = 1.906 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.4251 (1) ÅCell parameters from 29938 reflections
b = 10.6894 (3) Åθ = 2.9–32.0°
c = 14.5865 (3) ŵ = 1.47 mm−1
α = 108.910 (1)°T = 296 K
β = 91.447 (1)°Block, colourless
γ = 102.440 (1)°0.42 × 0.32 × 0.23 mm
V = 777.30 (3) Å3
Bruker X8 APEX diffractometer5388 independent reflections
Radiation source: fine-focus sealed tube3919 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
φ and ω scansθmax = 32.0°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)h = −8→8
Tmin = 0.739, Tmax = 0.867k = −15→15
29938 measured reflectionsl = −20→21
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.0369P)2 + 0.5008P] where P = (Fo2 + 2Fc2)/3
5388 reflections(Δ/σ)max < 0.001
217 parametersΔρmax = 0.92 e Å−3
0 restraintsΔρmin = −0.93 e Å−3
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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.
xyzUiso*/Ueq
Ag10.88258 (4)0.17155 (2)0.082506 (13)0.05506 (8)
S10.27700 (10)−0.00777 (6)0.27138 (4)0.03914 (12)
N10.9412 (3)0.2260 (2)0.25072 (14)0.0399 (4)
N20.5007 (4)0.0657 (2)0.13988 (14)0.0442 (4)
N30.2802 (4)−0.0253 (2)0.09364 (14)0.0435 (4)
N4−0.1644 (4)−0.2195 (2)0.02161 (14)0.0415 (4)
C11.1468 (4)0.3134 (3)0.30566 (19)0.0473 (5)
H11.27960.34770.27490.057*
C21.1710 (5)0.3552 (3)0.4058 (2)0.0568 (7)
H21.31890.41510.44140.068*
C30.9763 (6)0.3080 (3)0.4524 (2)0.0606 (7)
H30.98940.33500.52010.073*
C40.7590 (5)0.2191 (3)0.39710 (17)0.0491 (6)
H40.62210.18630.42680.059*
C50.7497 (4)0.1801 (2)0.29698 (16)0.0367 (4)
C60.5261 (4)0.0856 (2)0.23297 (15)0.0358 (4)
C70.1435 (4)−0.0725 (2)0.15227 (15)0.0349 (4)
C8−0.1038 (4)−0.1714 (2)0.11867 (15)0.0345 (4)
C9−0.2607 (4)−0.2091 (3)0.18250 (17)0.0428 (5)
H9−0.2114−0.17480.24920.051*
C10−0.4937 (5)−0.2991 (3)0.1457 (2)0.0476 (5)
H10−0.6027−0.32730.18710.057*
C11−0.5609 (5)−0.3460 (3)0.0472 (2)0.0477 (5)
H11−0.7186−0.40420.02100.057*
C12−0.3919 (5)−0.3058 (3)−0.01236 (18)0.0476 (5)
H12−0.4374−0.3400−0.07930.057*
O11.0220 (4)0.6251 (2)0.29332 (16)0.0703 (6)
O20.6832 (4)0.4674 (3)0.2406 (2)0.0785 (7)
O30.9959 (4)0.4677 (2)0.15475 (16)0.0695 (6)
N50.9004 (4)0.5189 (2)0.22918 (16)0.0474 (5)
O40.2764 (8)0.0495 (3)0.5333 (3)0.1395 (14)
H4A0.15110.08320.55590.209*
H4B0.40790.11630.55420.209*
O50.4863 (4)0.3278 (2)0.61006 (16)0.0730 (6)
H5A0.40200.37690.64970.109*
H5B0.63290.34530.64150.109*
U11U22U33U12U13U23
Ag10.05582 (12)0.06872 (16)0.03379 (10)−0.00435 (9)0.01077 (7)0.01998 (9)
S10.0410 (3)0.0453 (3)0.0288 (2)0.0034 (2)0.00920 (19)0.0134 (2)
N10.0394 (9)0.0424 (11)0.0376 (10)0.0057 (8)0.0089 (7)0.0152 (8)
N20.0441 (10)0.0516 (12)0.0328 (9)−0.0017 (8)0.0057 (7)0.0170 (9)
N30.0451 (10)0.0500 (12)0.0312 (9)−0.0005 (8)0.0055 (7)0.0153 (8)
N40.0433 (9)0.0430 (11)0.0335 (9)0.0051 (8)0.0079 (7)0.0096 (8)
C10.0407 (11)0.0489 (14)0.0491 (13)0.0011 (10)0.0063 (10)0.0185 (11)
C20.0464 (13)0.0549 (16)0.0543 (15)−0.0029 (11)−0.0047 (11)0.0091 (13)
C30.0604 (16)0.073 (2)0.0359 (13)0.0036 (14)−0.0014 (11)0.0101 (13)
C40.0462 (12)0.0605 (16)0.0370 (12)0.0039 (11)0.0085 (9)0.0168 (11)
C50.0377 (10)0.0376 (11)0.0352 (10)0.0076 (8)0.0075 (8)0.0135 (9)
C60.0377 (10)0.0381 (11)0.0335 (10)0.0077 (8)0.0104 (8)0.0151 (9)
C70.0390 (10)0.0364 (11)0.0296 (9)0.0094 (8)0.0078 (7)0.0110 (8)
C80.0378 (9)0.0330 (11)0.0331 (10)0.0098 (8)0.0078 (8)0.0105 (8)
C90.0442 (11)0.0481 (14)0.0375 (11)0.0081 (10)0.0116 (9)0.0176 (10)
C100.0427 (11)0.0496 (14)0.0540 (14)0.0082 (10)0.0157 (10)0.0232 (12)
C110.0405 (11)0.0409 (13)0.0555 (15)0.0031 (9)0.0061 (10)0.0124 (11)
C120.0474 (12)0.0468 (14)0.0387 (12)0.0017 (10)0.0030 (9)0.0076 (10)
O10.0593 (12)0.0748 (15)0.0585 (12)0.0083 (10)−0.0056 (10)0.0037 (11)
O20.0413 (10)0.0866 (16)0.1001 (18)0.0029 (10)0.0200 (11)0.0283 (14)
O30.0732 (13)0.0715 (14)0.0570 (12)0.0109 (11)0.0245 (10)0.0152 (11)
N50.0367 (9)0.0564 (13)0.0502 (12)0.0083 (9)0.0025 (8)0.0211 (10)
O40.169 (4)0.077 (2)0.154 (4)−0.004 (2)−0.004 (3)0.037 (2)
O50.0582 (11)0.0823 (16)0.0599 (13)0.0109 (11)0.0061 (10)0.0029 (11)
Ag1—N4i2.2785 (19)C3—H30.9300
Ag1—N12.3273 (19)C4—C51.379 (3)
Ag1—N22.4421 (19)C4—H40.9300
Ag1—N3i2.5519 (19)C5—C61.472 (3)
Ag1—O32.911 (2)C7—C81.476 (3)
S1—C61.719 (2)C8—C91.374 (3)
S1—C71.721 (2)C9—C101.386 (3)
N1—C11.334 (3)C9—H90.9300
N1—C51.343 (3)C10—C111.369 (4)
N2—C61.303 (3)C10—H100.9300
N2—N31.365 (3)C11—C121.376 (4)
N3—C71.299 (3)C11—H110.9300
N3—Ag1i2.5519 (19)C12—H120.9300
N4—C121.342 (3)O1—N51.247 (3)
N4—C81.345 (3)O2—N51.229 (3)
N4—Ag1i2.2785 (19)O3—N51.230 (3)
C1—C21.376 (4)O4—H4A0.8601
C1—H10.9300O4—H4B0.8601
C2—C31.365 (4)O5—H5A0.8601
C2—H20.9300O5—H5B0.8600
C3—C41.384 (4)
N4i—Ag1—N1129.5 (1)C5—C4—H4120.7
N4i—Ag1—N2159.9 (1)C3—C4—H4120.7
N1—Ag1—N270.1 (1)N1—C5—C4122.9 (2)
N4i—Ag1—N3i69.0 (1)N1—C5—C6115.1 (2)
N1—Ag1—N3i157.2 (1)C4—C5—C6122.0 (2)
N2—Ag1—N3i90.9 (1)N2—C6—C5121.8 (2)
N4i—Ag1—O379.4 (1)N2—C6—S1113.6 (2)
N1—Ag1—O376.6 (1)C5—C6—S1124.6 (2)
N2—Ag1—O3113.6 (1)N3—C7—C8122.4 (2)
N3i—Ag1—O3124.0 (1)N3—C7—S1113.7 (2)
C6—S1—C787.2 (1)C8—C7—S1123.9 (2)
C1—N1—C5117.4 (2)N4—C8—C9123.0 (2)
C1—N1—Ag1123.0 (2)N4—C8—C7114.9 (2)
C5—N1—Ag1119.2 (2)C9—C8—C7122.1 (2)
C6—N2—N3112.7 (2)C8—C9—C10118.7 (2)
C6—N2—Ag1113.1 (2)C8—C9—H9120.6
N3—N2—Ag1133.5 (2)C10—C9—H9120.6
C7—N3—N2112.8 (2)C11—C10—C9118.9 (2)
C7—N3—Ag1i109.7 (2)C11—C10—H10120.5
N2—N3—Ag1i135.3 (2)C9—C10—H10120.5
C12—N4—C8117.2 (2)C10—C11—C12119.1 (2)
C12—N4—Ag1i120.8 (2)C10—C11—H11120.5
C8—N4—Ag1i121.8 (2)C12—C11—H11120.5
N1—C1—C2123.0 (2)N4—C12—C11123.0 (2)
N1—C1—H1118.5N4—C12—H12118.5
C2—C1—H1118.5C11—C12—H12118.5
C3—C2—C1119.4 (2)N5—O3—Ag1115.4 (2)
C3—C2—H2120.3O2—N5—O3120.5 (2)
C1—C2—H2120.3O2—N5—O1119.2 (2)
C2—C3—C4118.7 (3)O3—N5—O1120.3 (2)
C2—C3—H3120.6H4A—O4—H4B104.9
C4—C3—H3120.6H5A—O5—H5B104.9
C5—C4—C3118.6 (2)
N4i—Ag1—N1—C111.5 (2)Ag1—N2—C6—S1−171.2 (1)
N2—Ag1—N1—C1−173.9 (2)N1—C5—C6—N2−10.6 (3)
N3i—Ag1—N1—C1150.9 (2)C4—C5—C6—N2168.9 (2)
O3—Ag1—N1—C1−52.4 (2)N1—C5—C6—S1169.5 (2)
N4i—Ag1—N1—C5−176.3 (2)C4—C5—C6—S1−11.0 (3)
N2—Ag1—N1—C5−1.7 (2)C7—S1—C6—N2−0.1 (2)
N3i—Ag1—N1—C5−36.8 (3)C7—S1—C6—C5179.8 (2)
O3—Ag1—N1—C5119.8 (2)N2—N3—C7—C8179.5 (2)
N4i—Ag1—N2—C6164.0 (2)Ag1i—N3—C7—C8−14.6 (3)
N1—Ag1—N2—C6−3.8 (2)N2—N3—C7—S10.0 (3)
N3i—Ag1—N2—C6163.3 (2)Ag1i—N3—C7—S1165.9 (1)
O3—Ag1—N2—C6−68.5 (2)C6—S1—C7—N30.1 (2)
N4i—Ag1—N2—N3−4.9 (4)C6—S1—C7—C8−179.5 (2)
N1—Ag1—N2—N3−172.7 (2)C12—N4—C8—C91.4 (3)
N3i—Ag1—N2—N3−5.6 (3)Ag1i—N4—C8—C9−173.6 (2)
O3—Ag1—N2—N3122.5 (2)C12—N4—C8—C7−177.5 (2)
C6—N2—N3—C70.0 (3)Ag1i—N4—C8—C77.5 (3)
Ag1—N2—N3—C7168.9 (2)N3—C7—C8—N46.5 (3)
C6—N2—N3—Ag1i−161.0 (2)S1—C7—C8—N4−174.0 (2)
Ag1—N2—N3—Ag1i8.0 (4)N3—C7—C8—C9−172.4 (2)
C5—N1—C1—C21.4 (4)S1—C7—C8—C97.1 (3)
Ag1—N1—C1—C2173.8 (2)N4—C8—C9—C10−1.0 (4)
N1—C1—C2—C3−1.2 (4)C7—C8—C9—C10177.9 (2)
C1—C2—C3—C4−0.1 (5)C8—C9—C10—C11−0.9 (4)
C2—C3—C4—C51.0 (5)C9—C10—C11—C122.1 (4)
C1—N1—C5—C4−0.4 (3)C8—N4—C12—C11−0.1 (4)
Ag1—N1—C5—C4−173.1 (2)Ag1i—N4—C12—C11175.0 (2)
C1—N1—C5—C6179.1 (2)C10—C11—C12—N4−1.7 (4)
Ag1—N1—C5—C66.4 (3)N4i—Ag1—O3—N5−174.6 (2)
C3—C4—C5—N1−0.8 (4)N1—Ag1—O3—N5−39.4 (2)
C3—C4—C5—C6179.8 (2)N2—Ag1—O3—N521.6 (2)
N3—N2—C6—C5−179.8 (2)N3i—Ag1—O3—N5129.9 (2)
Ag1—N2—C6—C58.9 (3)Ag1—O3—N5—O2−39.5 (3)
N3—N2—C6—S10.1 (3)Ag1—O3—N5—O1141.5 (2)
D—H···AD—HH···AD···AD—H···A
O4—H4B···O50.862.082.777 (4)138
O4—H4A···O4ii0.862.512.980 (9)115
C1—H1···O2iii0.932.443.342 (3)164
C12—H12···O2iv0.932.483.376 (4)162
O5—H5A···O2v0.862.052.874 (3)162
O5—H5A···O1v0.862.463.191 (3)143
O5—H5B···O1vi0.861.992.851 (3)176
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
O4—H4B⋯O50.862.082.777 (4)138
O4—H4A⋯O4i 0.862.512.980 (9)115
C1—H1⋯O2ii 0.932.443.342 (3)164
C12—H12⋯O2iii 0.932.483.376 (4)162
O5—H5A⋯O2iv 0.862.052.874 (3)162
O5—H5A⋯O1iv 0.862.463.191 (3)143
O5—H5B⋯O1v 0.861.992.851 (3)176

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .

  5 in total

1.  Developments in inorganic crystal engineering.

Authors:  Lee Brammer
Journal:  Chem Soc Rev       Date:  2004-09-24       Impact factor: 54.564

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  Reactivity of pyridine-2,4,6-tricarboxylic acid toward Zn(II) salts under different reaction conditions.

Authors:  Sujit K Ghosh; G Savitha; Parimal K Bharadwaj
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4.  Aqua-bis-[2,5-bis-(pyridin-2-yl)-1,3,4-thia-diazole-κ(2)N(2),N(3)](trifluoro-methane-sulfonato-κO)copper(II) trifluoro-methane-sulfonate.

Authors:  Fouad Bentiss; Moha Outirite; Michel Lagrenée; Mohamed Saadi; Lahcen El Ammari
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-03-03

5.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
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1.  Crystal structure of bis-(azido-κN)bis[2,5-bis(pyridin-2-yl)-1,3,4-thia-diazole-κ(2) N (2),N (3)]cobalt(II).

Authors:  Abdelhakim Laachir; Fouad Bentiss; Salaheddine Guesmi; Mohamed Saadi; Lahcen El Ammari
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2015-04-09

2.  Crystal structure of bis-(azido-κN)bis-[2,5-bis-(pyridin-2-yl)-1,3,4-thia-diazole-κ(2) N (2),N (3)]nickel(II).

Authors:  Abdelhakim Laachir; Fouad Bentiss; Salaheddine Guesmi; Mohamed Saadi; Lahcen El Ammari
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2015-01-14

3.  Crystal structure of bis-[2,5-bis-(pyridin-2-yl)-1,3,4-thia-diazole-κ(2) N (2),N (3)]bis-(thio-cyanato-κS)copper(II).

Authors:  Abdelhakim Laachir; Fouad Bentiss; Salaheddine Guesmi; Mohamed Saadi; Lahcen El Ammari
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2016-07-22
  3 in total

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