Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S205322961400312X/eg3149sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S205322961400312X/eg3149Isup2.hkl |
CCDC reference: 986362
In recent years, coordination polymers (CPs) have been widely investigated in coordination chemistry and materials science due to their intriguing structural diversities and potential applications, for example in adsorption/separation (Li et al., 2011), magnetism (Kurmoo, 2009), catalysis (Lee et al., 2009) and luminescence (Cui et al., 2012). In particular, CPs based on silver are of current interest because the AgI cation principally exhibits various coordination numbers and a high affinity even for hard donor atoms such as nitrogen or oxygen, and because it possesses a d10 electronic configuration with the possibility for direct Ag···Ag interactions and potential applications in luminescence (Cheng et al., 2011; Liu et al., 2012). From the viewpoint of crystal engineering, the rational selection of organic ligands assembling with AgI cations plays a very important role in the construction of the target silver CPs with desired structures and properties. Several silver(I) CPs with rigid organic ligands have been synthesized successfully; for example, Sun and co-workers have reported two silver(I) CPs constructed from rigid benzoguanamine and pyrazine-2-carboxylic acid or pyrazine-2,3-dicarboxylic acid as ligands (Sun, Hao et al., 2012). Huang et al. (2013) reported a silver(I) CP with the ligands benzene-1,3,5-tricarboxylic acid and pyrazine. In addition, Guo's group successfully obtained a three-dimensional silver(I) CP based on 2-phenylquinoline-4-carboxylate and 4,4'-bipyridine (Guo et al., 2013). However, less attention has hitherto been focused on flexible ligands, especially on asymmetric flexible bridges (Wei et al., 2009). In this work, we selected the asymmetric flexible N-donor ligand 4-{[(1-phenyl-1H-tetrazol-5-yl)sulfanyl]methyl}benzoate (ptmba; Zhang et al., 2012), which has at least three expected advantages: (i) strong coordination ability from the combination of carboxylate and tetrazole groups; (ii) a flexible conformation (due to the –SCH2– group) and asymmetric character; (iii) potentially rich supramolecular interactions, such as hydrogen bonds, π–π stacking and/or C—H···π interactions etc. Herein, we report the synthesis and crystal structure of the resulting one-dimensional silver(I) coordination polymer, (I), and discuss its thermal stability and luminescence properties.
All chemicals were purchased from commercial sources (Alfa–Aesar) and used without further purification. 4-{[(1-Phenyl-1H-tetrazol-5-yl)sulfanyl]methyl}benzoic acid (Hptmba) was synthesized according to our previously reported method (Zhang et al., 2012). For the preparation of (I), a solution of silver nitrate (0.085 g, 0.5 mmol) in acetonitrile (5 ml) was carefully layered onto an aqueous solution (5 ml) of Hptmba (0.156 g, 0.5 mmol) and triethylamine (0.051 g, 0.5 mmol). The system was left in a dark room for about 5 d at ambient temperature, and colourless block-shaped crystals of (I) suitable for X-ray analysis were obtained (yield 0.164 g, 78%, based on silver). Elemental analysis, calculated for C15H11AgN4O2S: C 42.98, H 2.64, N 13.36, S 7.65%; found: C 42.90, H 2.72, N 13.32, S 7.70%. Spectroscopic analysis: IR (KBr, ν, cm-1): 2984 (w), 1590 (s), 1498 (s), 1438 (m), 1387 (s), 1303 (m), 1178 (m), 850 (m), 806 (m), 734 (m), 711 (m), 693 (m), 630 (w).
Crystal data, data collection and structure refinement details are summarized in Table 1. C-bound H atoms were positioned geometrically, with C—H = 0.93 or 0.97 Å for aromatic or methylene H atoms, respectively, and refined using a riding model, with Uiso(H) = 1.2Ueq(C).
The title compound, (I), crystallizes in the monoclinic space group P21/c, and the asymmetric unit consists of one crystallographically independent AgI cation and one 4-{[(1-phenyl-1H-tetrazol-5-yl)sulfanyl]methyl}benzoate (ptmba-) ligand (Fig. 1). Each AgI cation is tricoordinated by two carboxylate O atoms and one tetrazole N atom from three different ptmba- ligands, displaying a distorted T-shaped geometry. The Ag—O and Ag—N bond lengths (Table 2) are comparable with those reported in other AgI compounds (Yin et al., 2009; Sun et al., 2011; Sun, Liu et al., 2012). In (I), the ptmba- ligand adopts a µ3-O:O':N4 tris-monodentate bridging mode. The two carboxylate C—O distances (Table 2) do not differ significantly, thus indicating substantial delocalization of the –CO2- π-electron density. The dihedral angle between the plane of the central tetrazole ring and that of the carboxylatobenzyl group is 82.92 (12)°, while the dihedral angle between the planes of the central tetrazole ring and the attached phenyl ring is 41.16 (16)°, which is smaller than that found in free Hptmba [61.66 (11)°; Zhang et al., 2012], indicating that interannular conjugation is insignificant or absent.
As shown in Fig. 2, each ptmba- ligand in (I) bridges three different AgI cations, and likewise each AgI cation connects to three different µ3-ptmba- ligands, thus generating an interesting one-dimensional [Ag(ptmba)]n double-chain structure along the c axis, which is similar to that found in the silver compound [Ag(HL)].H2O (L is the 4-hydroxy-3-nitrosonaphthalene-1-sulfonate anion; Wu et al., 2009). Alternatively, the coordination polymer [Ag(ptmba)]n can be understood as constructed from dimeric [Ag2(CO2)2] units linked by bridging µ3-ptmba- ligands. The distance between the AgI cations in the [Ag2(CO2)2] unit [Ag1···Ag1i = 2.9183 (7) Å; symmetry code: (i) -x + 2, -y + 1, -z + 2] is slightly longer than the Ag···Ag separation of 2.88 Å in the metal [Reference?], but significantly shorter than the van der Waals contact distance for Ag···Ag of 3.44 Å (Bondi, 1964). When compared with the related silver(I) coordination polymers [Ag(bpy)0.5].Hdpa (H2dpa = 1,1'-biphenyl-2,2'-dicarboxylic acid and bpy = 4,4'-bipyridine; Yin et al., 2009) and [Ag(abn)(4-cba)]2 (abn = 2-aminobenzonitrile and 4-cbaH = 4-chlorobenzoic acid; Sun, Liu et al., 2012), the Ag···Ag distance in the [Ag2(CO2)2] unit of (I) is longer than that in [Ag(abn)(4-cba)]2 [2.8950 (9) Å] but shorter than that in [Ag(bpy)0.5].Hdpa [2.9591 (2) Å], indicating the existence of ligand-supported argentophilic interactions (Wang & Mak, 2002).
An additional intrachain feature is the offset face-to-face π–π stacking between two adjacent benzene rings of -SCH2C6H4CO2- groups (Cg1···Cg1ii; Table 3). This π–π contact further consolidates the double-chain structure. Interchain contacts are present due to face-to-face π–π stacking between the two neighbouring phenyl rings of [C6H5N4C–] groups (Cg2···Cg2iii; Table 2), thus yielding a two-dimensional (4,4)-connected supramolecular network in the ac plane with rectangular windows (Fig. 3). The resulting layers are packed along the b axis, via additional π–π interactions between a benzene ring in the [–(SCH2C6H4CO2)-] group and a tetrazole ring (Cg1···Cg3iv; see Table 3 for details) to form a three-dimensional supramolecular framework (Fig. 4).
To determine the thermal stability of (I), thermogravimetric analysis (TGA) was carried out under a nitrogen atmosphere in the temperature range 308–973 K at a heating rate of 10 K min-1. The TG curve in Fig. 5(a) shows no obvious weight loss from 308 to 483 K; a rapid weight loss is observed upon further heating, indicating decomposition of the framework. This result confirms the absence of cocrystallized solvent molecules in (I), consistent with the single-crystal X-ray diffraction analysis. The powder X-ray diffraction (PXRD) pattern of an as-synthesized sample matches the simulation based on the single-crystal diffraction data and hence indicates phase purity of the product (Fig. 5b).
The photoluminescent properties of (I) were investigated at room temperature in the solid state. As shown in Fig. 6, (I) exhibits strong green luminescence, with a maximum at ca 546 nm upon excitation at 325 nm. Compared with the emission of the free Hptmba molecule (λem = 441 nm, λex = 325 nm), the emission band of (I) is red-shifted by ca 105 nm, and this may be due to the electronic transition between occupied p orbitals of coordinated N or O atoms and the empty 5s orbital of the AgI cation, i.e. ligand-to-metal charge transfer (LMCT), mixed with metal-centred (d–s/d–p) transitions. Similar observations have been made for other photoluminescent silver(I) compounds (Liu et al., 2005; Luo et al., 2009).
In summary, a new one-dimensional silver(I) coordination polymer has been successfully synthesized based on the asymmetric flexible N-donor 4-{[(1-phenyl-1H-tetrazol-5-yl)sulfanyl]methyl}benzoate ligand. The observed π–π interactions not only consolidate the intrachain one-dimensional structure but also help to link individual chains into a three-dimensional supramolecular framework. Thermogravimetry and fluorescence spectroscopy revealed that the new coordination polymer shows good thermal stability and strong green luminescence at room temperature.
Data collection: SMART (Bruker, 2001); cell refinement: SMART (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
[Ag(C15H11N4O2S)] | F(000) = 832 |
Mr = 419.21 | Dx = 1.803 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3290 reflections |
a = 15.1501 (13) Å | θ = 2.7–28.0° |
b = 8.2900 (7) Å | µ = 1.45 mm−1 |
c = 12.3879 (11) Å | T = 298 K |
β = 96.936 (2)° | Block, colourless |
V = 1544.5 (2) Å3 | 0.40 × 0.38 × 0.19 mm |
Z = 4 |
Bruker SMART 1000 CCD area-detector diffractometer | 3684 independent reflections |
Radiation source: fine-focus sealed tube | 2383 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.077 |
φ and ω scans | θmax = 28.0°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −20→8 |
Tmin = 0.594, Tmax = 0.770 | k = −10→10 |
9195 measured reflections | l = −15→16 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.119 | w = 1/[σ2(Fo2) + (0.050P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max = 0.001 |
3684 reflections | Δρmax = 0.78 e Å−3 |
209 parameters | Δρmin = −1.10 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0092 (9) |
[Ag(C15H11N4O2S)] | V = 1544.5 (2) Å3 |
Mr = 419.21 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 15.1501 (13) Å | µ = 1.45 mm−1 |
b = 8.2900 (7) Å | T = 298 K |
c = 12.3879 (11) Å | 0.40 × 0.38 × 0.19 mm |
β = 96.936 (2)° |
Bruker SMART 1000 CCD area-detector diffractometer | 3684 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 2383 reflections with I > 2σ(I) |
Tmin = 0.594, Tmax = 0.770 | Rint = 0.077 |
9195 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.119 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.78 e Å−3 |
3684 reflections | Δρmin = −1.10 e Å−3 |
209 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Ag1 | 1.08271 (2) | 0.42668 (4) | 0.97501 (2) | 0.05051 (17) | |
S1 | 0.76232 (8) | 0.33620 (12) | 0.27351 (7) | 0.0438 (3) | |
O1 | 0.8883 (2) | 0.5799 (3) | 0.8464 (2) | 0.0465 (7) | |
O2 | 0.9989 (2) | 0.4112 (3) | 0.81849 (19) | 0.0467 (7) | |
N1 | 0.6551 (2) | 0.3178 (4) | 0.0795 (2) | 0.0400 (8) | |
N2 | 0.6434 (3) | 0.3882 (5) | −0.0212 (3) | 0.0562 (10) | |
N3 | 0.7071 (3) | 0.4924 (5) | −0.0222 (3) | 0.0614 (11) | |
N4 | 0.7620 (2) | 0.4911 (4) | 0.0755 (2) | 0.0452 (8) | |
C1 | 0.9312 (3) | 0.4953 (4) | 0.7860 (3) | 0.0320 (8) | |
C2 | 0.9003 (3) | 0.4942 (4) | 0.6663 (2) | 0.0308 (8) | |
C3 | 0.9312 (3) | 0.3776 (5) | 0.5982 (3) | 0.0398 (9) | |
H3 | 0.9694 | 0.2969 | 0.6278 | 0.048* | |
C4 | 0.9052 (3) | 0.3816 (5) | 0.4862 (3) | 0.0406 (10) | |
H4 | 0.9251 | 0.3021 | 0.4420 | 0.049* | |
C5 | 0.8498 (3) | 0.5033 (4) | 0.4402 (3) | 0.0343 (8) | |
C6 | 0.8172 (3) | 0.6176 (4) | 0.5071 (3) | 0.0346 (8) | |
H6 | 0.7788 | 0.6976 | 0.4769 | 0.041* | |
C7 | 0.8419 (3) | 0.6130 (4) | 0.6195 (3) | 0.0343 (8) | |
H7 | 0.8193 | 0.6897 | 0.6636 | 0.041* | |
C8 | 0.8253 (3) | 0.5159 (5) | 0.3169 (3) | 0.0446 (10) | |
H8A | 0.8787 | 0.5223 | 0.2809 | 0.053* | |
H8B | 0.7899 | 0.6117 | 0.2988 | 0.053* | |
C9 | 0.7280 (3) | 0.3840 (4) | 0.1379 (3) | 0.0363 (9) | |
C10 | 0.5951 (3) | 0.1960 (5) | 0.1099 (3) | 0.0429 (10) | |
C11 | 0.6302 (4) | 0.0633 (5) | 0.1684 (4) | 0.0556 (12) | |
H11 | 0.6912 | 0.0526 | 0.1866 | 0.067* | |
C12 | 0.5722 (5) | −0.0535 (7) | 0.1991 (5) | 0.0818 (19) | |
H12 | 0.5941 | −0.1417 | 0.2403 | 0.098* | |
C13 | 0.4812 (5) | −0.0378 (8) | 0.1679 (5) | 0.0816 (19) | |
H13 | 0.4423 | −0.1170 | 0.1864 | 0.098* | |
C14 | 0.4501 (4) | 0.0925 (8) | 0.1110 (4) | 0.0778 (18) | |
H14 | 0.3891 | 0.1017 | 0.0908 | 0.093* | |
C15 | 0.5052 (3) | 0.2131 (6) | 0.0813 (3) | 0.0568 (12) | |
H15 | 0.4821 | 0.3033 | 0.0431 | 0.068* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ag1 | 0.0478 (3) | 0.0737 (3) | 0.02751 (19) | 0.00522 (18) | −0.00578 (14) | −0.00075 (13) |
S1 | 0.0517 (7) | 0.0466 (6) | 0.0298 (4) | −0.0125 (5) | −0.0088 (4) | 0.0028 (4) |
O1 | 0.056 (2) | 0.0565 (17) | 0.0265 (12) | 0.0103 (16) | 0.0054 (13) | −0.0024 (11) |
O2 | 0.0449 (18) | 0.0663 (18) | 0.0251 (12) | 0.0140 (16) | −0.0107 (12) | −0.0001 (11) |
N1 | 0.0393 (19) | 0.0488 (18) | 0.0302 (14) | −0.0097 (17) | −0.0030 (13) | −0.0014 (13) |
N2 | 0.053 (2) | 0.076 (3) | 0.0343 (17) | −0.016 (2) | −0.0160 (16) | 0.0094 (16) |
N3 | 0.066 (3) | 0.081 (3) | 0.0334 (18) | −0.022 (3) | −0.0120 (18) | 0.0119 (17) |
N4 | 0.045 (2) | 0.059 (2) | 0.0295 (15) | −0.009 (2) | −0.0022 (14) | 0.0054 (14) |
C1 | 0.035 (2) | 0.0360 (18) | 0.0241 (16) | −0.0085 (18) | 0.0002 (15) | 0.0005 (14) |
C2 | 0.035 (2) | 0.0339 (17) | 0.0229 (15) | −0.0057 (18) | 0.0024 (14) | −0.0022 (13) |
C3 | 0.048 (3) | 0.0356 (19) | 0.0346 (18) | 0.006 (2) | 0.0004 (17) | −0.0009 (15) |
C4 | 0.050 (3) | 0.041 (2) | 0.0287 (17) | 0.006 (2) | −0.0004 (17) | −0.0079 (15) |
C5 | 0.039 (2) | 0.0376 (18) | 0.0250 (16) | −0.0112 (19) | −0.0032 (15) | 0.0007 (14) |
C6 | 0.034 (2) | 0.0354 (18) | 0.0323 (17) | −0.0018 (18) | −0.0061 (15) | 0.0040 (14) |
C7 | 0.039 (2) | 0.0348 (18) | 0.0289 (17) | −0.0004 (18) | 0.0038 (16) | −0.0061 (14) |
C8 | 0.057 (3) | 0.050 (2) | 0.0240 (17) | −0.015 (2) | −0.0054 (17) | −0.0004 (15) |
C9 | 0.039 (2) | 0.0381 (19) | 0.0288 (17) | −0.0013 (19) | −0.0063 (15) | −0.0048 (14) |
C10 | 0.042 (2) | 0.050 (2) | 0.0356 (19) | −0.014 (2) | 0.0034 (17) | −0.0129 (17) |
C11 | 0.053 (3) | 0.052 (3) | 0.061 (3) | −0.013 (2) | 0.002 (2) | −0.004 (2) |
C12 | 0.097 (5) | 0.075 (4) | 0.073 (4) | −0.032 (4) | 0.009 (4) | 0.009 (3) |
C13 | 0.085 (5) | 0.102 (5) | 0.059 (3) | −0.048 (4) | 0.014 (3) | −0.008 (3) |
C14 | 0.043 (3) | 0.125 (5) | 0.067 (3) | −0.028 (4) | 0.012 (3) | −0.024 (3) |
C15 | 0.037 (2) | 0.081 (3) | 0.050 (2) | −0.006 (3) | −0.0051 (19) | −0.012 (2) |
Ag1—O1i | 2.204 (2) | C4—C5 | 1.390 (6) |
Ag1—O2 | 2.190 (3) | C4—H4 | 0.9300 |
Ag1—N4ii | 2.598 (4) | C5—C6 | 1.388 (5) |
Ag1—Ag1i | 2.9183 (7) | C5—C8 | 1.532 (4) |
S1—C9 | 1.743 (3) | C6—C7 | 1.398 (5) |
S1—C8 | 1.815 (4) | C6—H6 | 0.9300 |
C1—O1 | 1.261 (4) | C7—H7 | 0.9300 |
O1—Ag1i | 2.204 (2) | C8—H8A | 0.9700 |
C1—O2 | 1.265 (5) | C8—H8B | 0.9700 |
N1—C9 | 1.360 (5) | C10—C15 | 1.373 (6) |
N1—N2 | 1.370 (4) | C10—C11 | 1.387 (6) |
N1—C10 | 1.439 (5) | C11—C12 | 1.391 (7) |
N2—N3 | 1.295 (5) | C11—H11 | 0.9300 |
N3—N4 | 1.384 (4) | C12—C13 | 1.391 (10) |
N4—C9 | 1.322 (5) | C12—H12 | 0.9300 |
N4—Ag1ii | 2.598 (4) | C13—C14 | 1.344 (8) |
C1—C2 | 1.500 (4) | C13—H13 | 0.9300 |
C2—C3 | 1.401 (5) | C14—C15 | 1.381 (7) |
C2—C7 | 1.402 (5) | C14—H14 | 0.9300 |
C3—C4 | 1.396 (5) | C15—H15 | 0.9300 |
C3—H3 | 0.9300 | ||
O2—Ag1—O1i | 155.70 (13) | C5—C6—H6 | 119.9 |
O2—Ag1—N4ii | 104.32 (11) | C7—C6—H6 | 119.9 |
O1i—Ag1—N4ii | 99.92 (11) | C6—C7—C2 | 120.7 (3) |
O2—Ag1—Ag1i | 77.95 (8) | C6—C7—H7 | 119.6 |
O1i—Ag1—Ag1i | 82.48 (8) | C2—C7—H7 | 119.6 |
N4ii—Ag1—Ag1i | 140.16 (9) | C5—C8—S1 | 107.2 (2) |
C9—S1—C8 | 100.60 (17) | C5—C8—H8A | 110.3 |
C1—O1—Ag1i | 121.8 (2) | S1—C8—H8A | 110.3 |
C1—O2—Ag1 | 127.6 (2) | C5—C8—H8B | 110.3 |
C9—N1—N2 | 108.6 (3) | S1—C8—H8B | 110.3 |
C9—N1—C10 | 130.0 (3) | H8A—C8—H8B | 108.5 |
N2—N1—C10 | 121.4 (3) | N4—C9—N1 | 108.0 (3) |
N3—N2—N1 | 106.1 (3) | N4—C9—S1 | 128.6 (3) |
N2—N3—N4 | 110.9 (3) | N1—C9—S1 | 123.3 (3) |
C9—N4—N3 | 106.3 (3) | C15—C10—C11 | 121.5 (4) |
C9—N4—Ag1ii | 138.2 (3) | C15—C10—N1 | 119.9 (4) |
N3—N4—Ag1ii | 104.7 (2) | C11—C10—N1 | 118.6 (4) |
O1—C1—O2 | 125.0 (3) | C10—C11—C12 | 118.7 (5) |
O1—C1—C2 | 117.9 (3) | C10—C11—H11 | 120.7 |
O2—C1—C2 | 117.1 (3) | C12—C11—H11 | 120.7 |
C3—C2—C7 | 118.4 (3) | C13—C12—C11 | 119.7 (6) |
C3—C2—C1 | 120.8 (3) | C13—C12—H12 | 120.1 |
C7—C2—C1 | 120.7 (3) | C11—C12—H12 | 120.1 |
C4—C3—C2 | 120.5 (4) | C14—C13—C12 | 119.6 (6) |
C4—C3—H3 | 119.8 | C14—C13—H13 | 120.2 |
C2—C3—H3 | 119.8 | C12—C13—H13 | 120.2 |
C5—C4—C3 | 120.6 (3) | C13—C14—C15 | 122.4 (6) |
C5—C4—H4 | 119.7 | C13—C14—H14 | 118.8 |
C3—C4—H4 | 119.7 | C15—C14—H14 | 118.8 |
C6—C5—C4 | 119.5 (3) | C10—C15—C14 | 118.0 (5) |
C6—C5—C8 | 119.2 (3) | C10—C15—H15 | 121.0 |
C4—C5—C8 | 121.3 (3) | C14—C15—H15 | 121.0 |
C5—C6—C7 | 120.3 (3) |
Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) −x+2, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Ag(C15H11N4O2S)] |
Mr | 419.21 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 15.1501 (13), 8.2900 (7), 12.3879 (11) |
β (°) | 96.936 (2) |
V (Å3) | 1544.5 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.45 |
Crystal size (mm) | 0.40 × 0.38 × 0.19 |
Data collection | |
Diffractometer | Bruker SMART 1000 CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.594, 0.770 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9195, 3684, 2383 |
Rint | 0.077 |
(sin θ/λ)max (Å−1) | 0.661 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.119, 1.00 |
No. of reflections | 3684 |
No. of parameters | 209 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.78, −1.10 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Ag1—O1i | 2.204 (2) | Ag1—Ag1i | 2.9183 (7) |
Ag1—O2 | 2.190 (3) | C1—O1 | 1.261 (4) |
Ag1—N4ii | 2.598 (4) | C1—O2 | 1.265 (5) |
Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) −x+2, −y+1, −z+1. |
CCD is the centre-to-centre distance (distance between ring centroids), IPD is the interplanar distance (perpendicular distance from one plane to the neighbouring ring centroid) and SA is the slippage angle (angle subtended by the intercentroid vector to the plane normal); for details, see Janiak (2000). Cg1 is the centroid of the C2–C7 ring, Cg2 that of the C10–C15 ring and Cg3 that of the C9/N1–N4 ring. |
Group 1/group 2 | CCD (Å) | SA (°) | IPD (Å) |
Cg1···Cg1ii | 4.176 (3) | 36.4 | 3.361 |
Cg2···Cg2iii | 3.753 (3) | 24.1 | 3.427 |
Cg1···Cg3iv | 4.326 (2) | 17.7/21.0 | 4.038/4.121 |
Symmetry codes: (ii) -x+2, -y+1, -z+1; (iii) -x+1, -y, -z; (iv) x, -y+1/2, z+1/2. |