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AgI-containing coordination complexes have attracted attention because of their photoluminescence properties and anti­microbial activities and, in principle, these properties depend on the nature of the structural topologies. A novel two-dimensional silver(I) complex with the anti-inflammatory diclofenac molecule, namely bis­{μ-2-[2-(2,6-di­chloro­anilino)phen­yl]acetato-κ3O,O′:O}bis­(μ-2,5-di­methyl­pyrazine-κ2N:N′)silver(I), [Ag2(C14H10Cl2NO2)2(C6H8N2)]n, (I), has been synthesized and characterized by single-crystal X-ray diffraction, revealing that the AgI ions are chelated by the carboxyl­ate groups of the anionic 2-[2-(2,6-di­chloro­anilino)phen­yl]acetate (dicl) ligand in a μ312 coordination mode. Each dicl ligand links three AgI atoms to generate a one-dimensional infinite chain. Adjacent chains are connected through 2,5-di­methyl­pyrazine (dmpyz) ligands to form a two-dimensional layer structure parallel to the crystallographic bc plane. The layers are further connected by C—H...π inter­actions to generate a three-dimensional supra­molecular structure. Additionally, the most striking feature is that the structure contains an intra­molecular C—H ...Ag anagostic inter­action. Furthermore, the title complex has been tested for its in vitro anti­bacterial activity and is determined to be highly effective on the studied microorganisms.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229616017009/lf3042sup1.cif
Contains datablock I

mol

MDL mol file https://doi.org/10.1107/S2053229616017009/lf3042Isup2.mol
Supplementary material

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616017009/lf3042Isup3.hkl
Contains datablock I

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229616017009/lf3042sup4.pdf
FT-IT spectrum and additional packing diagram for (I)

CCDC reference: 1500645

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: WinGX (Farrugia, 2012); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: [Program(s) for molecular graphics?]; software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Bis{µ-2-[2-(2,6-dichloroanilino)phenyl]acetato-κ3O,O':O}bis(µ-2,5-dimethylpyrazine-κ2N:N')silver(I) top
Crystal data top
[Ag2(C14H10Cl2NO2)2(C6H8N2)]F(000) = 1816
Mr = 914.14Dx = 1.825 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 36.3376 (18) ÅCell parameters from 3828 reflections
b = 9.6778 (3) Åθ = 2.2–28.1°
c = 9.4818 (5) ŵ = 1.55 mm1
β = 93.860 (4)°T = 296 K
V = 3326.9 (3) Å3Needle, colourless
Z = 40.40 × 0.21 × 0.08 mm
Data collection top
Stoe IPDS 2
diffractometer
2948 reflections with I > 2σ(I)
w–scan rotation methodRint = 0.096
Absorption correction: integrationθmax = 27.6°, θmin = 2.2°
Tmin = 0.683, Tmax = 0.896h = 4747
15896 measured reflectionsk = 1212
3828 independent reflectionsl = 1212
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033H-atom parameters constrained
wR(F2) = 0.082 w = 1/[σ2(Fo2) + (0.0399P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.93(Δ/σ)max = 0.046
3828 reflectionsΔρmax = 1.04 e Å3
218 parametersΔρmin = 1.01 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.34208 (9)0.5797 (3)0.0806 (3)0.0370 (6)
C20.31875 (11)0.4894 (3)0.0058 (4)0.0460 (8)
H20.32830.41870.04730.055*
C30.28122 (11)0.5050 (3)0.0105 (4)0.0504 (8)
H30.26520.44790.04360.060*
C40.26731 (9)0.6052 (3)0.0952 (4)0.0434 (7)
H40.24200.61380.10140.052*
C50.29137 (8)0.6935 (3)0.1715 (3)0.0340 (6)
C60.32961 (8)0.6891 (3)0.1610 (3)0.0321 (6)
C70.34965 (7)0.9234 (3)0.2401 (3)0.0302 (5)
C80.32558 (8)0.9944 (3)0.1463 (3)0.0346 (6)
H80.31220.94630.07520.042*
C90.32130 (9)1.1360 (3)0.1571 (4)0.0428 (7)
H90.30511.18260.09380.051*
C100.34122 (10)1.2077 (3)0.2622 (4)0.0470 (8)
H100.33801.30250.27160.056*
C110.36591 (9)1.1380 (3)0.3535 (4)0.0419 (7)
H110.37961.18740.42300.050*
C120.37092 (7)0.9962 (3)0.3444 (3)0.0315 (6)
C130.39949 (8)0.9258 (3)0.4423 (3)0.0368 (6)
H13A0.39050.83570.46880.044*
H13B0.40390.98030.52770.044*
C140.43534 (7)0.9092 (3)0.3701 (3)0.0313 (6)
C150.51952 (9)0.5612 (3)0.1048 (4)0.0439 (7)
H150.53380.60220.17840.053*
C160.47711 (9)0.5805 (3)0.0836 (4)0.0414 (7)
C170.45276 (11)0.6686 (4)0.1798 (4)0.0557 (9)
H17A0.45600.76390.15360.083*
H17B0.42750.64260.17210.083*
H17C0.45920.65610.27550.083*
Cl10.38949 (3)0.55424 (9)0.07567 (11)0.0564 (2)
Cl20.27174 (2)0.80471 (8)0.28764 (9)0.04399 (18)
N10.35427 (7)0.7785 (2)0.2321 (3)0.0360 (5)
H10.37380.74340.27440.043*
N20.49669 (8)0.6406 (3)0.0239 (3)0.0433 (6)
O10.43415 (6)0.8361 (2)0.2602 (2)0.0396 (5)
O20.46352 (6)0.9689 (2)0.4205 (3)0.0459 (5)
Ag10.47925 (2)0.86905 (2)0.11173 (3)0.04030 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0435 (17)0.0306 (13)0.0371 (16)0.0013 (12)0.0045 (13)0.0042 (12)
C20.066 (2)0.0311 (14)0.0413 (17)0.0032 (14)0.0033 (16)0.0048 (13)
C30.061 (2)0.0373 (16)0.051 (2)0.0138 (15)0.0074 (17)0.0048 (15)
C40.0374 (16)0.0396 (16)0.0521 (19)0.0115 (13)0.0047 (14)0.0036 (14)
C50.0339 (14)0.0319 (13)0.0357 (15)0.0039 (11)0.0016 (12)0.0027 (12)
C60.0341 (15)0.0274 (12)0.0341 (15)0.0025 (11)0.0029 (11)0.0033 (11)
C70.0246 (13)0.0320 (13)0.0339 (14)0.0018 (10)0.0012 (11)0.0004 (11)
C80.0284 (14)0.0367 (14)0.0384 (16)0.0037 (11)0.0007 (12)0.0004 (12)
C90.0388 (16)0.0408 (15)0.0490 (18)0.0035 (13)0.0052 (14)0.0074 (15)
C100.053 (2)0.0318 (15)0.057 (2)0.0029 (14)0.0099 (17)0.0043 (14)
C110.0392 (16)0.0397 (15)0.0474 (18)0.0110 (13)0.0073 (14)0.0123 (14)
C120.0207 (12)0.0402 (14)0.0339 (14)0.0045 (10)0.0049 (10)0.0037 (12)
C130.0243 (13)0.0544 (17)0.0317 (15)0.0055 (12)0.0018 (11)0.0077 (13)
C140.0230 (12)0.0356 (13)0.0350 (15)0.0004 (10)0.0014 (11)0.0002 (11)
C150.0423 (17)0.0436 (17)0.0457 (19)0.0020 (13)0.0028 (14)0.0127 (15)
C160.0360 (16)0.0416 (15)0.0478 (18)0.0002 (12)0.0108 (14)0.0096 (14)
C170.051 (2)0.0512 (19)0.064 (2)0.0076 (16)0.0025 (18)0.0053 (17)
Cl10.0472 (5)0.0473 (4)0.0756 (6)0.0134 (4)0.0114 (4)0.0004 (4)
Cl20.0365 (4)0.0443 (4)0.0521 (5)0.0013 (3)0.0099 (3)0.0032 (3)
N10.0268 (12)0.0314 (11)0.0483 (15)0.0013 (9)0.0088 (10)0.0022 (11)
N20.0439 (14)0.0373 (13)0.0490 (16)0.0004 (11)0.0053 (12)0.0106 (12)
O10.0294 (10)0.0492 (12)0.0403 (12)0.0048 (9)0.0042 (9)0.0121 (9)
O20.0221 (10)0.0551 (13)0.0599 (14)0.0025 (9)0.0012 (10)0.0218 (11)
Ag10.03129 (12)0.04507 (14)0.04485 (15)0.00259 (10)0.00490 (9)0.00503 (11)
Geometric parameters (Å, º) top
C1—C21.380 (5)C12—C131.508 (4)
C1—C61.398 (4)C13—C141.520 (4)
C1—Cl11.744 (3)C14—O21.243 (3)
C2—C31.376 (5)C14—O11.258 (4)
C3—C41.377 (5)C15—N21.335 (5)
C4—C51.390 (4)C15—C16i1.392 (4)
C5—C61.400 (4)C16—N21.337 (4)
C5—Cl21.728 (3)C16—C15i1.392 (4)
C6—N11.387 (4)C16—C171.495 (5)
C7—C81.387 (4)N2—Ag12.460 (2)
C7—C121.403 (4)O1—Ag12.254 (2)
C7—N11.415 (4)O2—Ag1ii2.332 (2)
C8—C91.384 (4)O2—Ag1iii2.436 (2)
C9—C101.379 (5)Ag1—O2ii2.332 (2)
C10—C111.380 (5)Ag1—O2iv2.436 (2)
C11—C121.387 (4)Ag1—Ag1ii2.9356 (5)
C2—C1—C6123.3 (3)O2—C14—C13119.1 (2)
C2—C1—Cl1118.1 (2)O1—C14—C13116.7 (2)
C6—C1—Cl1118.6 (2)N2—C15—C16i122.8 (3)
C3—C2—C1119.3 (3)N2—C16—C15i119.4 (3)
C2—C3—C4120.0 (3)N2—C16—C17118.6 (3)
C3—C4—C5119.6 (3)C15i—C16—C17121.9 (3)
C4—C5—C6122.5 (3)C6—N1—C7124.7 (2)
C4—C5—Cl2116.3 (2)C15—N2—C16117.7 (3)
C6—C5—Cl2121.2 (2)C15—N2—Ag1119.2 (2)
N1—C6—C1121.0 (3)C16—N2—Ag1120.9 (2)
N1—C6—C5124.0 (3)C14—O1—Ag1116.88 (17)
C1—C6—C5114.9 (3)C14—O2—Ag1ii118.44 (18)
C8—C7—C12119.8 (3)C14—O2—Ag1iii136.99 (19)
C8—C7—N1121.9 (3)Ag1ii—O2—Ag1iii101.40 (8)
C12—C7—N1118.3 (2)O1—Ag1—O2ii146.39 (8)
C9—C8—C7120.8 (3)O1—Ag1—O2iv114.32 (8)
C10—C9—C8119.7 (3)O2ii—Ag1—O2iv78.60 (8)
C9—C10—C11119.7 (3)O1—Ag1—N2107.40 (8)
C10—C11—C12121.8 (3)O2ii—Ag1—N294.33 (9)
C11—C12—C7118.2 (3)O2iv—Ag1—N2112.30 (9)
C11—C12—C13119.8 (3)O1—Ag1—Ag1ii78.08 (6)
C7—C12—C13122.1 (3)O2ii—Ag1—Ag1ii73.02 (6)
C12—C13—C14110.2 (2)O2iv—Ag1—Ag1ii138.20 (6)
O2—C14—O1124.1 (3)N2—Ag1—Ag1ii100.00 (7)
C6—C1—C2—C30.8 (5)C8—C7—C12—C13175.5 (3)
Cl1—C1—C2—C3178.5 (3)N1—C7—C12—C133.0 (4)
C1—C2—C3—C43.5 (5)C11—C12—C13—C1495.7 (3)
C2—C3—C4—C52.4 (5)C7—C12—C13—C1482.4 (3)
C3—C4—C5—C63.0 (5)C12—C13—C14—O2117.1 (3)
C3—C4—C5—Cl2174.0 (2)C12—C13—C14—O161.9 (3)
C2—C1—C6—N1178.7 (3)C1—C6—N1—C7138.9 (3)
Cl1—C1—C6—N12.0 (4)C5—C6—N1—C746.1 (4)
C2—C1—C6—C55.8 (4)C8—C7—N1—C618.4 (4)
Cl1—C1—C6—C5173.5 (2)C12—C7—N1—C6163.2 (3)
C4—C5—C6—N1177.8 (3)C16i—C15—N2—C161.7 (5)
Cl2—C5—C6—N15.3 (4)C16i—C15—N2—Ag1161.7 (2)
C4—C5—C6—C16.8 (4)C15i—C16—N2—C151.6 (5)
Cl2—C5—C6—C1170.0 (2)C17—C16—N2—C15177.0 (3)
C12—C7—C8—C92.2 (4)C15i—C16—N2—Ag1161.4 (2)
N1—C7—C8—C9179.4 (3)C17—C16—N2—Ag119.9 (4)
C7—C8—C9—C100.1 (5)O2—C14—O1—Ag119.9 (4)
C8—C9—C10—C111.6 (5)C13—C14—O1—Ag1159.1 (2)
C9—C10—C11—C121.2 (5)O1—C14—O2—Ag1ii30.4 (4)
C10—C11—C12—C70.9 (4)C13—C14—O2—Ag1ii150.7 (2)
C10—C11—C12—C13177.2 (3)O1—C14—O2—Ag1iii174.1 (2)
C8—C7—C12—C112.6 (4)C13—C14—O2—Ag1iii4.8 (5)
N1—C7—C12—C11179.0 (3)
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y, z+1/2; (iii) x, y+2, z+1/2; (iv) x, y+2, z1/2.
Hydrogen-bond geometry (Å, º) top
Cg is the centre of the aromatic ring, Cg3 is the centre of the dmpyz ring and Cg5 is the centre of the C7–C12 ring.
D—H···AD—HH···AD···AD—H···A
C15—H15···O1ii0.932.593.356 (4)140
N1—H1···O10.862.382.950 (3)124
C17—H17A···Ag10.962.793.460127
C17—H17C···Cg3v0.963.073.9408151
C13—H13B···Cg5vi0.973.123.6237114
C8—H8···Cg5vii0.933.393.9145118
Symmetry codes: (ii) x+1, y, z+1/2; (v) x+1/2, y+1/2, z+1/2; (vi) x+1/2, y+3/2, z1/2; (vii) x+1/2, y+3/2, z+1/2.
Selected IR spectral dataa for the dicl ligand and (I) top
AssignmentNadicl(I)
ν (NH)3250 (m)3273 (m)
νar(CH)3060 (vw)3090–3022 (vw)
νal(CH)2980 (vw)2963–2910 (vw)
νas(COO)1572 (vs)1579 (vs)
νs(COO)1399 (w)1451 (vs), 1380 (vs)
ν(CCl)768 (s)746 (vs)
Frequencies are in cm-1; w = weak, m = medium, s = strong, vs = very strong and vw = ???.
Antimicrobial activities of (I) as MIC values (µg ml-1) top
MicroorganismNadicl(I)VancomycinCiprofloxacinAmphotericine-B
Gram (+) bacteria
MRSA>10243281-
S. aureus2561620,125-
E. feacalis2561620,25-
B. cereus2561622-
L. monocytogenes2563210,5-
Gram (-) bacteria
E. coli>102432-0,0625-
S. typhi>102432-0,0625-
Yeast
C. albicans10241--0,025
 

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