metal-organic compounds
Diacetonitrile(3-{2-[8-(2-bromoethoxy)-9,10-dioxoanthracen-1-yloxy]ethyl}-1-(2-pyridylmethyl)imidazolium)silver(I) bis(hexafluoridophosphate)
aSchool of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China
*Correspondence e-mail: qindabincwnu@yahoo.com.cn
The title compound, [Ag(C27H23BrN3O4)(CH3CN)2](PF6)2, is a mononuclear salt species in which the silver(I) atom is coordinated by one ligand and two acetonitrile molecules and exhibits a distorted T-shaped coordination. The contains one independent cation and two independent hexafluoridophosphate anions, one of which is disordered over two positions in a 0.756 (11):0.244 (11) ratio. Weak π–π interactions between the anthraquinone ring systems [centroid–centroid distance = 3.676 (3) Å], intermolecular Ag–π interactions [Cg⋯Ag = 3.405 Å] and C—H⋯π interactions between pairs of adjacent molecules are observed.
Related literature
For the synthesis of 1,8-bis(2-bromoethoxy)anthraquinone, see: Chen et al. (1992) and of 2-[(1H-imidazol-1-yl)methyl]pyridine, see: Chiu et al. (2005). For related structures, see: Mahajan et al. (2001, 2002). For Ag–π interactions, see: Mascal et al. (2000).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 2000); cell SAINT (Bruker, 2000); data reduction: SAINT; 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: SHELXL97 and PLATON (Spek, 2009).
Supporting information
https://doi.org/10.1107/S1600536810029739/si2276sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810029739/si2276Isup2.hkl
1,8-Bis(2-bromoethoxy)anthraquinone (Chen et al., 1992) (1.92 g, 10 mmol) was added to a solution of 2-((1H-imidazol-1-yl)methyl)pyridine (Chiu et al., 2005) (2.48 g, 20 mmol) in 50 ml of THF. The mixture was refluxed for 48 h. The resulting precipitate was isolated and washed with THF(2 × 5 ml) and was then dissolved in methanol (20 ml). To the aqueous solution was added an excess of NH4PF6 resulting in a yellow precipitation. The yellow solid was collected and washed with water and Et2O and dried under vacuum. The title compound was synthesized from the reaction of a slurry of Ag2O (64 mg, 0.275 mmol) in 10 ml of acetonitrile was treated with the yellow soild (213 mg, 0.50 mmol). The mixture was stirred for 12 h with exclusion of light at 323 K until nearly all Ag2O was dissolved. The filtrate was concentrated to ca 2 ml. Addition of Et2O (20 ml) to the filtrate yielded a yellow solid. Yellow single crystals suitable for X-ray diffraction were obtained by recrystallization from acetonitrile.
H atoms were placed in calculated positions with C—H = 0.93–0.97 Å, and refined in riding mode with Uiso(H) = 1.2Ueq(C), and Uiso(H) = 1.5Ueq(C) for the acetonitrile methyl group. In one of the hexafluorophosphate anions five F atoms were found to be disordered over two sites with occupancies 0.756 (11) and 0.244 (11). The disorder was completed with a combination of PLATON (Spek, 2009) and SHELXL97 (Sheldrick, 2008).
Anthraquinone derivatives have attracted much attention due to their optical and photosemiconducting properties (Mahajan et al., 2001, 2002).
The silver(I) atom is bridged by the pyridyl N-atom from one ligand and two acetonitrile molecules and exhibits distorted T shaped coordination (Table 1, Fig. 1). The imidazole rings make dihedral angles with the attached pyridine ring of 61.07 (15)° and anthraquinone ring of 44.80 (10)°. The carbonyl atoms O2 and O4 are almost coplane with the anthraquinone plane, the dihedral angle between the planes of the C23/C24/C25/O2 and C16/C17/C18/O4 fragments is 1.02 (27)°. (Fig. 1).
The π–π interactions between the anthraquinone ring systems of the inversion related molecules, with a Cg3···Cg4i distance of 3.676 (3) Å, [symmetry code i: 1 - x, 2 - y, 2 - z] where Cg3 is the C12—C16/C25 ring centroid and Cg4 is the C16—C18/C23—C25 ring centroid (Fig. 2), and two adjacent molecules are bridged by Ag···π interactions involving the pyridyl rings: [Cg2···Ag1ii = 3.405 Å, (Fig. 2). Cg2 is the N1/C1—C5 ring centroid, symmetry code ii: 1 - x, 1 - y, 1 - z]. The present values are thus outside the range of Ag-centroid distances of 2.89–3.37 Å (Mascal et al., 2000). Besides, the structure is further stabilized by C—H···π intermolecular interactions involving the ethoxy carbon C26 and one of the anthraquinone rings [H26B···Cg3iii = 2.98 Å, C26—H26B··· Cg3iii = 148°, and a weaker contact between one of the acetonitrile donors and the imidazole ring is observed H31B···Cg1iv = 3.38 Å, C31—H31B···Cg1iv = 108°. Cg1 and Cg3 are the centroids of the N2/N3/C7—C9 imidazole rings and C12—C16/C25 anthraquinone rings]. Symmetry code for the two interactions, iii: 2 - x, 2 - y, 2 - z; iv: -x, 1 - y, 1 - z.
is stabilized byFor the synthesis of 1,8-bis(2-bromoethoxy)anthraquinone, see: Chen et al. (1992) and of 2-[(1H-imidazol-1-yl)methyl]pyridine, see: Chiu et al. (2005). For related structures, see: Mahajan et al. (2001, 2002). For Ag–π interactions, see: Mascal et al. (2000).
Data collection: SMART (Bruker, 2000); cell
SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).[Ag(C27H23BrN3O4)(C2H3N)2](PF6)2 | Z = 2 |
Mr = 1013.31 | F(000) = 1004 |
Triclinic, P1 | Dx = 1.878 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.961 (3) Å | Cell parameters from 6148 reflections |
b = 12.826 (4) Å | θ = 1.6–27.9° |
c = 18.199 (6) Å | µ = 1.88 mm−1 |
α = 89.034 (14)° | T = 116 K |
β = 88.278 (12)° | Prism, colorless |
γ = 74.805 (7)° | 0.20 × 0.18 × 0.16 mm |
V = 1792.3 (10) Å3 |
Bruker SMART CCD area-detector diffractometer | 6327 independent reflections |
Radiation source: fine-focus sealed tube | 5355 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.062 |
Detector resolution: 14.63 pixels mm-1 | θmax = 25.0°, θmin = 1.1° |
ω and φ scans | h = −9→9 |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | k = −15→15 |
Tmin = 0.706, Tmax = 0.754 | l = −21→21 |
18740 measured reflections |
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)] = 0.053 | H-atom parameters constrained |
wR(F2) = 0.132 | w = 1/[σ2(Fo2) + (0.0714P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.005 |
6327 reflections | Δρmax = 0.95 e Å−3 |
554 parameters | Δρmin = −1.24 e Å−3 |
107 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: 0.0390 (15) |
[Ag(C27H23BrN3O4)(C2H3N)2](PF6)2 | γ = 74.805 (7)° |
Mr = 1013.31 | V = 1792.3 (10) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.961 (3) Å | Mo Kα radiation |
b = 12.826 (4) Å | µ = 1.88 mm−1 |
c = 18.199 (6) Å | T = 116 K |
α = 89.034 (14)° | 0.20 × 0.18 × 0.16 mm |
β = 88.278 (12)° |
Bruker SMART CCD area-detector diffractometer | 6327 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | 5355 reflections with I > 2σ(I) |
Tmin = 0.706, Tmax = 0.754 | Rint = 0.062 |
18740 measured reflections |
R[F2 > 2σ(F2)] = 0.053 | 107 restraints |
wR(F2) = 0.132 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.95 e Å−3 |
6327 reflections | Δρmin = −1.24 e Å−3 |
554 parameters |
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. |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Ag1 | 0.81202 (5) | 0.46133 (3) | 0.492136 (19) | 0.02593 (16) | |
Br1 | 1.00740 (8) | 0.58237 (5) | 0.87898 (3) | 0.0448 (2) | |
P1 | 0.80962 (15) | 0.90464 (9) | 0.40606 (6) | 0.0183 (3) | |
P2 | 0.60236 (17) | 0.47473 (9) | 0.77493 (7) | 0.0245 (3) | |
F1 | 0.6881 (4) | 0.8274 (2) | 0.38733 (15) | 0.0309 (6) | |
F2 | 0.9560 (3) | 0.8403 (2) | 0.34916 (13) | 0.0267 (6) | |
F3 | 0.7208 (4) | 0.9869 (2) | 0.34205 (13) | 0.0286 (6) | |
F4 | 0.9307 (4) | 0.9829 (2) | 0.42395 (14) | 0.0297 (6) | |
F5 | 0.6638 (3) | 0.9684 (2) | 0.46379 (13) | 0.0285 (6) | |
F6 | 0.8966 (3) | 0.8235 (2) | 0.47089 (13) | 0.0279 (6) | |
F8 | 0.5481 (5) | 0.5903 (2) | 0.81166 (17) | 0.0503 (9) | |
F7A | 0.6754 (11) | 0.3596 (5) | 0.7368 (4) | 0.058 (2) | 0.756 (11) |
F9A | 0.4254 (8) | 0.4499 (6) | 0.7960 (4) | 0.0705 (19) | 0.756 (11) |
F10A | 0.6775 (11) | 0.4261 (5) | 0.8501 (3) | 0.0568 (18) | 0.756 (11) |
F11A | 0.7834 (6) | 0.5029 (5) | 0.7539 (4) | 0.0573 (17) | 0.756 (11) |
F12A | 0.5296 (11) | 0.5322 (5) | 0.6986 (3) | 0.062 (2) | 0.756 (11) |
F7B | 0.590 (3) | 0.3654 (15) | 0.7364 (12) | 0.046 (5) | 0.244 (11) |
F9B | 0.3932 (18) | 0.5058 (17) | 0.7743 (11) | 0.058 (5) | 0.244 (11) |
F10B | 0.586 (2) | 0.4211 (14) | 0.8544 (8) | 0.039 (4) | 0.244 (11) |
F11B | 0.8056 (18) | 0.439 (2) | 0.7781 (11) | 0.077 (5) | 0.244 (11) |
F12B | 0.621 (3) | 0.5124 (16) | 0.6922 (8) | 0.049 (5) | 0.244 (11) |
O1 | 0.6449 (4) | 1.0682 (2) | 0.82082 (15) | 0.0216 (7) | |
O2 | 0.8220 (5) | 0.9164 (3) | 0.90418 (16) | 0.0362 (9) | |
O3 | 1.0398 (4) | 0.7780 (2) | 0.98270 (16) | 0.0257 (7) | |
O4 | 0.5994 (5) | 1.1618 (3) | 1.14206 (18) | 0.0418 (9) | |
N1 | 0.5981 (5) | 0.6198 (3) | 0.49115 (18) | 0.0183 (8) | |
N2 | 0.7119 (5) | 0.7748 (3) | 0.64378 (18) | 0.0175 (8) | |
N3 | 0.7046 (5) | 0.9302 (3) | 0.68965 (18) | 0.0183 (8) | |
N4 | 0.9818 (5) | 0.4191 (3) | 0.5892 (2) | 0.0250 (9) | |
N5 | 0.8324 (5) | 0.3673 (3) | 0.3871 (2) | 0.0269 (9) | |
C1 | 0.4750 (6) | 0.6286 (4) | 0.4402 (2) | 0.0221 (10) | |
H1 | 0.4891 | 0.5739 | 0.4058 | 0.027* | |
C2 | 0.3295 (6) | 0.7149 (4) | 0.4368 (2) | 0.0234 (10) | |
H2 | 0.2485 | 0.7193 | 0.4003 | 0.028* | |
C3 | 0.3068 (6) | 0.7957 (3) | 0.4897 (2) | 0.0232 (10) | |
H3 | 0.2086 | 0.8541 | 0.4898 | 0.028* | |
C4 | 0.4321 (6) | 0.7873 (3) | 0.5416 (2) | 0.0199 (9) | |
H4 | 0.4192 | 0.8401 | 0.5772 | 0.024* | |
C5 | 0.5769 (6) | 0.7000 (3) | 0.5405 (2) | 0.0176 (9) | |
C6 | 0.7295 (6) | 0.6862 (3) | 0.5915 (2) | 0.0202 (9) | |
H6A | 0.7429 | 0.6192 | 0.6189 | 0.024* | |
H6B | 0.8349 | 0.6799 | 0.5618 | 0.024* | |
C7 | 0.7110 (6) | 0.8763 (3) | 0.6279 (2) | 0.0210 (10) | |
H7 | 0.7143 | 0.9050 | 0.5808 | 0.025* | |
C8 | 0.7039 (7) | 0.8602 (4) | 0.7485 (2) | 0.0261 (11) | |
H8 | 0.7017 | 0.8767 | 0.7981 | 0.031* | |
C9 | 0.7073 (6) | 0.7634 (4) | 0.7195 (2) | 0.0240 (10) | |
H9 | 0.7065 | 0.7006 | 0.7456 | 0.029* | |
C10 | 0.7066 (7) | 1.0449 (3) | 0.6937 (2) | 0.0241 (10) | |
H10A | 0.6794 | 1.0784 | 0.6458 | 0.029* | |
H10B | 0.8232 | 1.0484 | 0.7051 | 0.029* | |
C11 | 0.5801 (6) | 1.1092 (3) | 0.7502 (2) | 0.0237 (10) | |
H11A | 0.5744 | 1.1855 | 0.7456 | 0.028* | |
H11B | 0.4644 | 1.0997 | 0.7439 | 0.028* | |
C12 | 0.5707 (6) | 1.1236 (3) | 0.8828 (2) | 0.0196 (9) | |
C13 | 0.4385 (6) | 1.2174 (3) | 0.8799 (3) | 0.0246 (10) | |
H13 | 0.3939 | 1.2440 | 0.8347 | 0.030* | |
C14 | 0.3706 (6) | 1.2731 (4) | 0.9440 (3) | 0.0286 (11) | |
H14 | 0.2796 | 1.3356 | 0.9415 | 0.034* | |
C15 | 0.4388 (6) | 1.2352 (4) | 1.0106 (3) | 0.0299 (11) | |
H15 | 0.3952 | 1.2729 | 1.0532 | 0.036* | |
C16 | 0.5722 (6) | 1.1412 (4) | 1.0147 (2) | 0.0230 (10) | |
C17 | 0.6479 (6) | 1.1053 (4) | 1.0879 (2) | 0.0277 (11) | |
C18 | 0.7802 (6) | 1.0009 (4) | 1.0945 (2) | 0.0245 (10) | |
C19 | 0.8386 (7) | 0.9673 (4) | 1.1646 (2) | 0.0303 (12) | |
H19 | 0.7945 | 1.0098 | 1.2052 | 0.036* | |
C20 | 0.9628 (7) | 0.8701 (4) | 1.1732 (2) | 0.0310 (12) | |
H20 | 1.0008 | 0.8475 | 1.2201 | 0.037* | |
C21 | 1.0319 (7) | 0.8060 (4) | 1.1136 (2) | 0.0279 (11) | |
H21 | 1.1157 | 0.7410 | 1.1204 | 0.033* | |
C22 | 0.9738 (6) | 0.8400 (4) | 1.0423 (2) | 0.0206 (10) | |
C23 | 0.8463 (6) | 0.9375 (3) | 1.0320 (2) | 0.0206 (10) | |
C24 | 0.7757 (6) | 0.9741 (3) | 0.9574 (2) | 0.0198 (10) | |
C25 | 0.6409 (6) | 1.0806 (3) | 0.9513 (2) | 0.0193 (9) | |
C26 | 1.1559 (6) | 0.6745 (4) | 0.9962 (2) | 0.0276 (11) | |
H26A | 1.0995 | 0.6313 | 1.0277 | 0.033* | |
H26B | 1.2590 | 0.6824 | 1.0203 | 0.033* | |
C27 | 1.2049 (7) | 0.6212 (4) | 0.9225 (3) | 0.0335 (12) | |
H27A | 1.2995 | 0.5566 | 0.9285 | 0.040* | |
H27B | 1.2456 | 0.6700 | 0.8895 | 0.040* | |
C28 | 1.0521 (6) | 0.3993 (3) | 0.6423 (3) | 0.0216 (10) | |
C29 | 1.1464 (7) | 0.3739 (4) | 0.7117 (3) | 0.0310 (11) | |
H29A | 1.2696 | 0.3538 | 0.7012 | 0.046* | |
H29B | 1.1138 | 0.3150 | 0.7363 | 0.046* | |
H29C | 1.1172 | 0.4362 | 0.7427 | 0.046* | |
C30 | 0.8236 (6) | 0.3136 (4) | 0.3397 (3) | 0.0266 (11) | |
C31 | 0.8093 (7) | 0.2415 (4) | 0.2798 (3) | 0.0383 (13) | |
H31A | 0.8302 | 0.1688 | 0.2983 | 0.057* | |
H31B | 0.8938 | 0.2447 | 0.2416 | 0.057* | |
H31C | 0.6945 | 0.2639 | 0.2603 | 0.057* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ag1 | 0.0270 (2) | 0.0223 (2) | 0.0255 (2) | −0.00068 (16) | −0.00450 (15) | −0.00217 (15) |
Br1 | 0.0453 (4) | 0.0449 (4) | 0.0436 (4) | −0.0092 (3) | −0.0102 (3) | −0.0097 (3) |
P1 | 0.0207 (6) | 0.0191 (6) | 0.0130 (6) | −0.0012 (5) | −0.0021 (4) | 0.0012 (5) |
P2 | 0.0289 (7) | 0.0217 (6) | 0.0232 (6) | −0.0068 (5) | −0.0067 (5) | 0.0027 (5) |
F1 | 0.0292 (16) | 0.0306 (15) | 0.0346 (15) | −0.0105 (13) | −0.0048 (12) | 0.0012 (12) |
F2 | 0.0294 (15) | 0.0287 (14) | 0.0195 (13) | −0.0040 (12) | 0.0066 (11) | −0.0033 (11) |
F3 | 0.0364 (16) | 0.0287 (15) | 0.0169 (13) | −0.0014 (12) | −0.0066 (11) | 0.0089 (11) |
F4 | 0.0333 (16) | 0.0279 (14) | 0.0301 (15) | −0.0107 (13) | −0.0076 (12) | −0.0040 (12) |
F5 | 0.0312 (16) | 0.0242 (14) | 0.0214 (13) | 0.0075 (12) | 0.0056 (11) | 0.0005 (11) |
F6 | 0.0295 (15) | 0.0271 (14) | 0.0188 (13) | 0.0073 (12) | −0.0032 (11) | 0.0065 (11) |
F8 | 0.075 (3) | 0.0322 (17) | 0.0439 (19) | −0.0153 (17) | 0.0184 (17) | −0.0086 (14) |
F7A | 0.101 (5) | 0.025 (2) | 0.048 (3) | −0.019 (3) | 0.016 (4) | −0.014 (2) |
F9A | 0.052 (3) | 0.069 (4) | 0.104 (4) | −0.041 (3) | 0.001 (3) | 0.003 (4) |
F10A | 0.081 (5) | 0.047 (3) | 0.039 (3) | −0.008 (3) | −0.029 (3) | 0.017 (2) |
F11A | 0.031 (3) | 0.039 (3) | 0.101 (4) | −0.010 (2) | 0.021 (2) | −0.008 (3) |
F12A | 0.100 (5) | 0.045 (3) | 0.030 (3) | 0.003 (3) | −0.032 (3) | 0.003 (2) |
F7B | 0.077 (9) | 0.025 (6) | 0.040 (7) | −0.020 (7) | −0.004 (8) | −0.006 (5) |
F9B | 0.039 (7) | 0.064 (9) | 0.073 (8) | −0.015 (7) | −0.009 (6) | −0.010 (7) |
F10B | 0.047 (7) | 0.043 (6) | 0.031 (6) | −0.017 (6) | −0.002 (6) | 0.007 (5) |
F11B | 0.056 (7) | 0.086 (9) | 0.084 (8) | −0.009 (7) | −0.007 (6) | 0.002 (7) |
F12B | 0.063 (9) | 0.042 (7) | 0.039 (7) | −0.014 (7) | 0.014 (7) | 0.019 (6) |
O1 | 0.0293 (18) | 0.0182 (15) | 0.0139 (15) | 0.0003 (13) | −0.0081 (13) | −0.0001 (12) |
O2 | 0.056 (2) | 0.0275 (18) | 0.0143 (17) | 0.0098 (17) | −0.0124 (16) | −0.0040 (14) |
O3 | 0.034 (2) | 0.0247 (17) | 0.0147 (15) | −0.0007 (14) | −0.0071 (13) | 0.0042 (13) |
O4 | 0.055 (3) | 0.049 (2) | 0.0219 (19) | −0.014 (2) | 0.0068 (17) | −0.0133 (17) |
N1 | 0.023 (2) | 0.0153 (18) | 0.0153 (18) | −0.0027 (15) | −0.0030 (15) | 0.0011 (15) |
N2 | 0.021 (2) | 0.0151 (18) | 0.0160 (18) | −0.0034 (15) | −0.0044 (15) | 0.0016 (15) |
N3 | 0.026 (2) | 0.0179 (18) | 0.0122 (18) | −0.0070 (16) | −0.0040 (15) | 0.0020 (15) |
N4 | 0.024 (2) | 0.0193 (19) | 0.029 (2) | −0.0021 (17) | −0.0014 (18) | 0.0023 (17) |
N5 | 0.029 (2) | 0.029 (2) | 0.022 (2) | −0.0064 (18) | −0.0064 (17) | −0.0001 (18) |
C1 | 0.026 (3) | 0.022 (2) | 0.020 (2) | −0.009 (2) | −0.0059 (19) | 0.0000 (19) |
C2 | 0.022 (2) | 0.027 (2) | 0.023 (2) | −0.010 (2) | −0.0094 (19) | 0.004 (2) |
C3 | 0.019 (2) | 0.019 (2) | 0.031 (3) | −0.0040 (19) | −0.0051 (19) | 0.0036 (19) |
C4 | 0.023 (2) | 0.016 (2) | 0.021 (2) | −0.0057 (18) | −0.0014 (18) | −0.0008 (18) |
C5 | 0.021 (2) | 0.016 (2) | 0.017 (2) | −0.0072 (18) | −0.0028 (17) | 0.0023 (17) |
C6 | 0.024 (2) | 0.017 (2) | 0.018 (2) | −0.0010 (18) | −0.0066 (18) | −0.0029 (18) |
C7 | 0.028 (3) | 0.023 (2) | 0.012 (2) | −0.006 (2) | −0.0053 (18) | 0.0029 (18) |
C8 | 0.042 (3) | 0.025 (2) | 0.014 (2) | −0.013 (2) | −0.004 (2) | 0.0014 (19) |
C9 | 0.038 (3) | 0.021 (2) | 0.014 (2) | −0.010 (2) | −0.0018 (19) | 0.0009 (18) |
C10 | 0.043 (3) | 0.017 (2) | 0.015 (2) | −0.012 (2) | −0.004 (2) | 0.0027 (18) |
C11 | 0.035 (3) | 0.017 (2) | 0.018 (2) | −0.005 (2) | −0.0090 (19) | 0.0026 (18) |
C12 | 0.020 (2) | 0.022 (2) | 0.020 (2) | −0.0101 (19) | −0.0017 (18) | −0.0020 (18) |
C13 | 0.025 (3) | 0.022 (2) | 0.027 (2) | −0.005 (2) | −0.003 (2) | 0.001 (2) |
C14 | 0.026 (3) | 0.021 (2) | 0.038 (3) | −0.005 (2) | 0.002 (2) | −0.007 (2) |
C15 | 0.031 (3) | 0.028 (3) | 0.031 (3) | −0.009 (2) | 0.012 (2) | −0.010 (2) |
C16 | 0.027 (3) | 0.025 (2) | 0.022 (2) | −0.014 (2) | 0.0038 (19) | −0.0032 (19) |
C17 | 0.033 (3) | 0.033 (3) | 0.021 (2) | −0.018 (2) | 0.006 (2) | −0.007 (2) |
C18 | 0.031 (3) | 0.036 (3) | 0.014 (2) | −0.022 (2) | 0.0004 (19) | 0.002 (2) |
C19 | 0.044 (3) | 0.043 (3) | 0.012 (2) | −0.028 (3) | 0.002 (2) | −0.004 (2) |
C20 | 0.047 (3) | 0.045 (3) | 0.012 (2) | −0.032 (3) | −0.011 (2) | 0.009 (2) |
C21 | 0.034 (3) | 0.034 (3) | 0.021 (2) | −0.017 (2) | −0.011 (2) | 0.008 (2) |
C22 | 0.025 (3) | 0.029 (2) | 0.013 (2) | −0.016 (2) | −0.0044 (18) | 0.0019 (18) |
C23 | 0.026 (2) | 0.025 (2) | 0.016 (2) | −0.015 (2) | −0.0014 (18) | −0.0019 (18) |
C24 | 0.026 (3) | 0.023 (2) | 0.013 (2) | −0.011 (2) | −0.0039 (18) | 0.0018 (19) |
C25 | 0.024 (2) | 0.019 (2) | 0.016 (2) | −0.0082 (19) | 0.0023 (18) | −0.0031 (18) |
C26 | 0.030 (3) | 0.025 (2) | 0.027 (3) | −0.006 (2) | −0.007 (2) | 0.006 (2) |
C27 | 0.029 (3) | 0.034 (3) | 0.035 (3) | −0.003 (2) | −0.002 (2) | −0.002 (2) |
C28 | 0.020 (2) | 0.016 (2) | 0.027 (3) | −0.0017 (18) | 0.001 (2) | −0.0034 (19) |
C29 | 0.034 (3) | 0.027 (3) | 0.030 (3) | −0.003 (2) | −0.011 (2) | −0.002 (2) |
C30 | 0.025 (3) | 0.029 (3) | 0.026 (3) | −0.007 (2) | −0.004 (2) | 0.003 (2) |
C31 | 0.048 (4) | 0.033 (3) | 0.032 (3) | −0.006 (3) | −0.006 (2) | −0.011 (2) |
Ag1—N4 | 2.230 (4) | C6—H6A | 0.9700 |
Ag1—N5 | 2.256 (4) | C6—H6B | 0.9700 |
Ag1—N1 | 2.284 (4) | C7—H7 | 0.9300 |
Br1—C27 | 1.961 (5) | C8—C9 | 1.351 (6) |
P1—F2 | 1.601 (3) | C8—H8 | 0.9300 |
P1—F1 | 1.602 (3) | C9—H9 | 0.9300 |
P1—F5 | 1.606 (3) | C10—C11 | 1.511 (6) |
P1—F4 | 1.606 (3) | C10—H10A | 0.9700 |
P1—F6 | 1.608 (2) | C10—H10B | 0.9700 |
P1—F3 | 1.609 (3) | C11—H11A | 0.9700 |
P2—F9A | 1.560 (5) | C11—H11B | 0.9700 |
P2—F11B | 1.564 (14) | C12—C13 | 1.376 (6) |
P2—F10A | 1.563 (5) | C12—C25 | 1.424 (6) |
P2—F7A | 1.600 (6) | C13—C14 | 1.397 (6) |
P2—F8 | 1.585 (3) | C13—H13 | 0.9300 |
P2—F11A | 1.609 (5) | C14—C15 | 1.372 (7) |
P2—F12A | 1.612 (5) | C14—H14 | 0.9300 |
P2—F7B | 1.607 (15) | C15—C16 | 1.385 (7) |
P2—F9B | 1.608 (14) | C15—H15 | 0.9300 |
P2—F10B | 1.608 (13) | C16—C25 | 1.415 (6) |
P2—F12B | 1.588 (14) | C16—C17 | 1.494 (6) |
O1—C12 | 1.376 (5) | C17—C18 | 1.476 (7) |
O1—C11 | 1.438 (5) | C18—C19 | 1.394 (6) |
O2—C24 | 1.217 (5) | C18—C23 | 1.414 (6) |
O3—C22 | 1.364 (5) | C19—C20 | 1.382 (7) |
O3—C26 | 1.427 (5) | C19—H19 | 0.9300 |
O4—C17 | 1.225 (5) | C20—C21 | 1.382 (7) |
N1—C5 | 1.351 (5) | C20—H20 | 0.9300 |
N1—C1 | 1.351 (5) | C21—C22 | 1.415 (6) |
N2—C7 | 1.326 (5) | C21—H21 | 0.9300 |
N2—C9 | 1.384 (5) | C22—C23 | 1.403 (6) |
N2—C6 | 1.471 (5) | C23—C24 | 1.506 (6) |
N3—C7 | 1.321 (5) | C24—C25 | 1.505 (6) |
N3—C8 | 1.386 (5) | C26—C27 | 1.510 (7) |
N3—C10 | 1.479 (5) | C26—H26A | 0.9700 |
N4—C28 | 1.122 (6) | C26—H26B | 0.9700 |
N5—C30 | 1.129 (6) | C27—H27A | 0.9700 |
C1—C2 | 1.379 (6) | C27—H27B | 0.9700 |
C1—H1 | 0.9300 | C28—C29 | 1.476 (6) |
C2—C3 | 1.398 (6) | C29—H29A | 0.9600 |
C2—H2 | 0.9300 | C29—H29B | 0.9600 |
C3—C4 | 1.377 (6) | C29—H29C | 0.9600 |
C3—H3 | 0.9300 | C30—C31 | 1.467 (7) |
C4—C5 | 1.381 (6) | C31—H31A | 0.9600 |
C4—H4 | 0.9300 | C31—H31B | 0.9600 |
C5—C6 | 1.522 (6) | C31—H31C | 0.9600 |
N4—Ag1—N5 | 127.22 (14) | N2—C6—C5 | 114.4 (3) |
N4—Ag1—N1 | 119.44 (13) | N2—C6—H6A | 108.6 |
N5—Ag1—N1 | 113.27 (13) | C5—C6—H6A | 108.6 |
F2—P1—F1 | 90.22 (15) | N2—C6—H6B | 108.6 |
F2—P1—F5 | 179.42 (16) | C5—C6—H6B | 108.6 |
F1—P1—F5 | 89.84 (15) | H6A—C6—H6B | 107.6 |
F2—P1—F4 | 89.66 (15) | N3—C7—N2 | 109.3 (4) |
F1—P1—F4 | 179.30 (16) | N3—C7—H7 | 125.4 |
F5—P1—F4 | 90.28 (15) | N2—C7—H7 | 125.4 |
F2—P1—F6 | 90.03 (14) | C9—C8—N3 | 106.5 (4) |
F1—P1—F6 | 90.27 (15) | C9—C8—H8 | 126.8 |
F5—P1—F6 | 89.39 (14) | N3—C8—H8 | 126.8 |
F4—P1—F6 | 90.42 (15) | C8—C9—N2 | 107.4 (4) |
F2—P1—F3 | 90.77 (14) | C8—C9—H9 | 126.3 |
F1—P1—F3 | 89.85 (15) | N2—C9—H9 | 126.3 |
F5—P1—F3 | 89.81 (14) | N3—C10—C11 | 114.1 (4) |
F4—P1—F3 | 89.46 (14) | N3—C10—H10A | 108.7 |
F6—P1—F3 | 179.18 (16) | C11—C10—H10A | 108.7 |
F9A—P2—F11B | 148.0 (9) | N3—C10—H10B | 108.7 |
F9A—P2—F10A | 90.0 (4) | C11—C10—H10B | 108.7 |
F11B—P2—F10A | 64.6 (8) | H10A—C10—H10B | 107.6 |
F9A—P2—F7A | 92.0 (3) | O1—C11—C10 | 106.2 (4) |
F11B—P2—F7A | 70.3 (8) | O1—C11—H11A | 110.5 |
F10A—P2—F7A | 90.5 (4) | C10—C11—H11A | 110.5 |
F9A—P2—F8 | 93.4 (3) | O1—C11—H11B | 110.5 |
F11B—P2—F8 | 104.5 (9) | C10—C11—H11B | 110.5 |
F10A—P2—F8 | 88.7 (3) | H11A—C11—H11B | 108.7 |
F7A—P2—F8 | 174.5 (4) | C13—C12—O1 | 122.7 (4) |
F9A—P2—F11A | 178.8 (3) | C13—C12—C25 | 120.8 (4) |
F10A—P2—F11A | 90.0 (3) | O1—C12—C25 | 116.5 (4) |
F7A—P2—F11A | 89.2 (3) | C12—C13—C14 | 120.9 (4) |
F8—P2—F11A | 85.4 (2) | C12—C13—H13 | 119.5 |
F9A—P2—F12A | 92.6 (4) | C14—C13—H13 | 119.5 |
F11B—P2—F12A | 114.0 (8) | C15—C14—C13 | 119.6 (5) |
F10A—P2—F12A | 176.0 (3) | C15—C14—H14 | 120.2 |
F7A—P2—F12A | 92.5 (4) | C13—C14—H14 | 120.2 |
F8—P2—F12A | 88.1 (3) | C14—C15—C16 | 120.4 (4) |
F11A—P2—F12A | 87.4 (3) | C14—C15—H15 | 119.8 |
F9A—P2—F7B | 69.7 (8) | C16—C15—H15 | 119.8 |
F11B—P2—F7B | 94.2 (10) | C15—C16—C25 | 121.7 (4) |
F10A—P2—F7B | 98.9 (9) | C15—C16—C17 | 118.6 (4) |
F8—P2—F7B | 161.3 (8) | C25—C16—C17 | 119.7 (4) |
F11A—P2—F7B | 111.5 (8) | O4—C17—C18 | 120.4 (4) |
F12A—P2—F7B | 84.8 (9) | O4—C17—C16 | 120.2 (5) |
F11B—P2—F9B | 177.1 (10) | C18—C17—C16 | 119.5 (4) |
F10A—P2—F9B | 113.1 (7) | C19—C18—C23 | 121.1 (5) |
F7A—P2—F9B | 108.4 (7) | C19—C18—C17 | 117.5 (4) |
F8—P2—F9B | 76.8 (7) | C23—C18—C17 | 121.4 (4) |
F11A—P2—F9B | 150.1 (8) | C20—C19—C18 | 119.4 (4) |
F12A—P2—F9B | 68.5 (7) | C20—C19—H19 | 120.3 |
F7B—P2—F9B | 84.4 (9) | C18—C19—H19 | 120.3 |
F9A—P2—F10B | 62.8 (6) | C19—C20—C21 | 121.5 (4) |
F11B—P2—F10B | 90.8 (9) | C19—C20—H20 | 119.3 |
F7A—P2—F10B | 92.6 (7) | C21—C20—H20 | 119.3 |
F8—P2—F10B | 89.2 (6) | C20—C21—C22 | 119.4 (5) |
F11A—P2—F10B | 117.2 (7) | C20—C21—H21 | 120.3 |
F12A—P2—F10B | 155.0 (7) | C22—C21—H21 | 120.3 |
F7B—P2—F10B | 90.0 (11) | O3—C22—C23 | 119.2 (4) |
F9B—P2—F10B | 86.7 (9) | O3—C22—C21 | 120.5 (4) |
F9A—P2—F12B | 115.1 (7) | C23—C22—C21 | 120.3 (4) |
F11B—P2—F12B | 88.7 (10) | C22—C23—C18 | 118.3 (4) |
F10A—P2—F12B | 153.3 (7) | C22—C23—C24 | 121.9 (4) |
F7A—P2—F12B | 80.1 (8) | C18—C23—C24 | 119.8 (4) |
F8—P2—F12B | 98.3 (7) | O2—C24—C25 | 121.3 (4) |
F11A—P2—F12B | 65.1 (7) | O2—C24—C23 | 120.4 (4) |
F7B—P2—F12B | 82.6 (11) | C25—C24—C23 | 118.3 (4) |
F9B—P2—F12B | 93.7 (9) | C16—C25—C12 | 116.6 (4) |
F10B—P2—F12B | 172.5 (10) | C16—C25—C24 | 121.0 (4) |
C12—O1—C11 | 118.6 (3) | C12—C25—C24 | 122.4 (4) |
C22—O3—C26 | 117.3 (3) | O3—C26—C27 | 107.0 (4) |
C5—N1—C1 | 118.0 (4) | O3—C26—H26A | 110.3 |
C5—N1—Ag1 | 125.6 (3) | C27—C26—H26A | 110.3 |
C1—N1—Ag1 | 116.1 (3) | O3—C26—H26B | 110.3 |
C7—N2—C9 | 108.1 (3) | C27—C26—H26B | 110.3 |
C7—N2—C6 | 126.9 (4) | H26A—C26—H26B | 108.6 |
C9—N2—C6 | 124.8 (3) | C26—C27—Br1 | 111.7 (3) |
C7—N3—C8 | 108.7 (4) | C26—C27—H27A | 109.3 |
C7—N3—C10 | 124.6 (3) | Br1—C27—H27A | 109.3 |
C8—N3—C10 | 126.6 (3) | C26—C27—H27B | 109.3 |
C28—N4—Ag1 | 173.0 (4) | Br1—C27—H27B | 109.3 |
C30—N5—Ag1 | 169.3 (4) | H27A—C27—H27B | 107.9 |
N1—C1—C2 | 123.0 (4) | N4—C28—C29 | 179.2 (5) |
N1—C1—H1 | 118.5 | C28—C29—H29A | 109.5 |
C2—C1—H1 | 118.5 | C28—C29—H29B | 109.5 |
C1—C2—C3 | 118.3 (4) | H29A—C29—H29B | 109.5 |
C1—C2—H2 | 120.8 | C28—C29—H29C | 109.5 |
C3—C2—H2 | 120.8 | H29A—C29—H29C | 109.5 |
C4—C3—C2 | 118.9 (4) | H29B—C29—H29C | 109.5 |
C4—C3—H3 | 120.5 | N5—C30—C31 | 178.0 (5) |
C2—C3—H3 | 120.5 | C30—C31—H31A | 109.5 |
C3—C4—C5 | 119.7 (4) | C30—C31—H31B | 109.5 |
C3—C4—H4 | 120.2 | H31A—C31—H31B | 109.5 |
C5—C4—H4 | 120.2 | C30—C31—H31C | 109.5 |
N1—C5—C4 | 122.1 (4) | H31A—C31—H31C | 109.5 |
N1—C5—C6 | 113.6 (4) | H31B—C31—H31C | 109.5 |
C4—C5—C6 | 124.3 (4) | ||
N4—Ag1—N1—C5 | 9.4 (4) | C15—C16—C17—O4 | −4.4 (7) |
N5—Ag1—N1—C5 | −167.7 (3) | C25—C16—C17—O4 | 173.9 (4) |
N4—Ag1—N1—C1 | −164.6 (3) | C15—C16—C17—C18 | 175.1 (4) |
N5—Ag1—N1—C1 | 18.2 (3) | C25—C16—C17—C18 | −6.6 (6) |
N5—Ag1—N4—C28 | −129 (3) | O4—C17—C18—C19 | 3.7 (7) |
N1—Ag1—N4—C28 | 55 (3) | C16—C17—C18—C19 | −175.8 (4) |
N4—Ag1—N5—C30 | 96 (2) | O4—C17—C18—C23 | −175.9 (4) |
N1—Ag1—N5—C30 | −87 (2) | C16—C17—C18—C23 | 4.6 (6) |
C5—N1—C1—C2 | −0.4 (6) | C23—C18—C19—C20 | −0.2 (7) |
Ag1—N1—C1—C2 | 174.1 (3) | C17—C18—C19—C20 | −179.8 (4) |
N1—C1—C2—C3 | −1.5 (7) | C18—C19—C20—C21 | 0.7 (7) |
C1—C2—C3—C4 | 1.6 (6) | C19—C20—C21—C22 | −0.3 (7) |
C2—C3—C4—C5 | 0.1 (6) | C26—O3—C22—C23 | −173.8 (4) |
C1—N1—C5—C4 | 2.2 (6) | C26—O3—C22—C21 | 5.6 (6) |
Ag1—N1—C5—C4 | −171.7 (3) | C20—C21—C22—O3 | −179.9 (4) |
C1—N1—C5—C6 | −175.5 (4) | C20—C21—C22—C23 | −0.5 (6) |
Ag1—N1—C5—C6 | 10.5 (5) | O3—C22—C23—C18 | −179.7 (4) |
C3—C4—C5—N1 | −2.1 (6) | C21—C22—C23—C18 | 0.9 (6) |
C3—C4—C5—C6 | 175.4 (4) | O3—C22—C23—C24 | 2.1 (6) |
C7—N2—C6—C5 | −66.6 (6) | C21—C22—C23—C24 | −177.3 (4) |
C9—N2—C6—C5 | 118.8 (4) | C19—C18—C23—C22 | −0.6 (6) |
N1—C5—C6—N2 | 177.8 (4) | C17—C18—C23—C22 | 179.0 (4) |
C4—C5—C6—N2 | 0.1 (6) | C19—C18—C23—C24 | 177.7 (4) |
C8—N3—C7—N2 | 0.9 (5) | C17—C18—C23—C24 | −2.7 (6) |
C10—N3—C7—N2 | 178.2 (4) | C22—C23—C24—O2 | 3.8 (7) |
C9—N2—C7—N3 | −0.5 (5) | C18—C23—C24—O2 | −174.5 (4) |
C6—N2—C7—N3 | −175.8 (4) | C22—C23—C24—C25 | −179.1 (4) |
C7—N3—C8—C9 | −1.0 (5) | C18—C23—C24—C25 | 2.6 (6) |
C10—N3—C8—C9 | −178.2 (4) | C15—C16—C25—C12 | 2.5 (6) |
N3—C8—C9—N2 | 0.7 (5) | C17—C16—C25—C12 | −175.8 (4) |
C7—N2—C9—C8 | −0.1 (5) | C15—C16—C25—C24 | −175.0 (4) |
C6—N2—C9—C8 | 175.3 (4) | C17—C16—C25—C24 | 6.7 (6) |
C7—N3—C10—C11 | 137.8 (4) | C13—C12—C25—C16 | −2.2 (6) |
C8—N3—C10—C11 | −45.3 (6) | O1—C12—C25—C16 | 176.1 (4) |
C12—O1—C11—C10 | 169.7 (3) | C13—C12—C25—C24 | 175.2 (4) |
N3—C10—C11—O1 | 68.5 (5) | O1—C12—C25—C24 | −6.5 (6) |
C11—O1—C12—C13 | −0.9 (6) | O2—C24—C25—C16 | 172.3 (4) |
C11—O1—C12—C25 | −179.2 (4) | C23—C24—C25—C16 | −4.8 (6) |
O1—C12—C13—C14 | −177.9 (4) | O2—C24—C25—C12 | −5.0 (7) |
C25—C12—C13—C14 | 0.4 (7) | C23—C24—C25—C12 | 177.9 (4) |
C12—C13—C14—C15 | 1.4 (7) | C22—O3—C26—C27 | 178.1 (4) |
C13—C14—C15—C16 | −1.1 (7) | O3—C26—C27—Br1 | −69.2 (4) |
C14—C15—C16—C25 | −0.8 (7) | Ag1—N4—C28—C29 | −146 (40) |
C14—C15—C16—C17 | 177.5 (4) | Ag1—N5—C30—C31 | −17 (17) |
Cg1 and Cg3 are the centroids of the N2/N3/C7–C9 imidazole rings and C12–C16/C25 anthraquinone rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C26—H26B···Cg3i | 0.97 | 2.98 | 3.845 (5) | 148 |
C31—H31B···Cg1ii | 0.96 | 3.38 | 3.781 (4) | 108 |
Symmetry codes: (i) −x+2, −y+2, −z+2; (ii) −x, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Ag(C27H23BrN3O4)(C2H3N)2](PF6)2 |
Mr | 1013.31 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 116 |
a, b, c (Å) | 7.961 (3), 12.826 (4), 18.199 (6) |
α, β, γ (°) | 89.034 (14), 88.278 (12), 74.805 (7) |
V (Å3) | 1792.3 (10) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.88 |
Crystal size (mm) | 0.20 × 0.18 × 0.16 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2000) |
Tmin, Tmax | 0.706, 0.754 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18740, 6327, 5355 |
Rint | 0.062 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.132, 1.07 |
No. of reflections | 6327 |
No. of parameters | 554 |
No. of restraints | 107 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.95, −1.24 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
Cg1 and Cg3 are the centroids of the N2/N3/C7–C9 imidazole rings and C12–C16/C25 anthraquinone rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C26—H26B···Cg3i | 0.97 | 2.98 | 3.845 (5) | 148 |
C31—H31B···Cg1ii | 0.96 | 3.38 | 3.781 (4) | 108 |
Symmetry codes: (i) −x+2, −y+2, −z+2; (ii) −x, −y+1, −z+1. |
Acknowledgements
The authors thank the Scientific Researching Fund Projects of China West Normal University (grant No. 06B003) and the Youth Fund Projects of Sichuan Educational Department (grant No. 2006B039).
References
Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, Z. H., Schall, O. F., Alcalá, M., Li, Y., Gokel, G. W. & Echegoyen, L. (1992). J. Am. Chem. Soc. 114, 444–451. CrossRef CAS Web of Science Google Scholar
Chiu, P. L., Lai, C. L., Chang, C. F., Hu, C. H. & Lee, H. M. (2005). Organometallics, 24, 6169–6178. Web of Science CSD CrossRef CAS Google Scholar
Mahajan, A., Bedi, P. K., Kaur, P. & Kumar, S. (2001). Thin Solid Films, 398, 82–86. Web of Science CrossRef Google Scholar
Mahajan, A., Bedi, P. K., Kaur, P. & Kumar, S. (2002). Thin Solid Films, 420, 392–397. Web of Science CrossRef Google Scholar
Mascal, M., Kerdelhué, J. L., Blake, A. J., Cooke, P. A., Mortimer, R. J. & Teat, S. J. (2000). Eur. J. Inorg. Chem. pp. 485–490. CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Anthraquinone derivatives have attracted much attention due to their optical and photosemiconducting properties (Mahajan et al., 2001, 2002).
The silver(I) atom is bridged by the pyridyl N-atom from one ligand and two acetonitrile molecules and exhibits distorted T shaped coordination (Table 1, Fig. 1). The imidazole rings make dihedral angles with the attached pyridine ring of 61.07 (15)° and anthraquinone ring of 44.80 (10)°. The carbonyl atoms O2 and O4 are almost coplane with the anthraquinone plane, the dihedral angle between the planes of the C23/C24/C25/O2 and C16/C17/C18/O4 fragments is 1.02 (27)°. (Fig. 1).
The crystal structure is stabilized by π–π interactions between the anthraquinone ring systems of the inversion related molecules, with a Cg3···Cg4i distance of 3.676 (3) Å, [symmetry code i: 1 - x, 2 - y, 2 - z] where Cg3 is the C12—C16/C25 ring centroid and Cg4 is the C16—C18/C23—C25 ring centroid (Fig. 2), and two adjacent molecules are bridged by Ag···π interactions involving the pyridyl rings: [Cg2···Ag1ii = 3.405 Å, (Fig. 2). Cg2 is the N1/C1—C5 ring centroid, symmetry code ii: 1 - x, 1 - y, 1 - z]. The present values are thus outside the range of Ag-centroid distances of 2.89–3.37 Å (Mascal et al., 2000). Besides, the structure is further stabilized by C—H···π intermolecular interactions involving the ethoxy carbon C26 and one of the anthraquinone rings [H26B···Cg3iii = 2.98 Å, C26—H26B··· Cg3iii = 148°, and a weaker contact between one of the acetonitrile donors and the imidazole ring is observed H31B···Cg1iv = 3.38 Å, C31—H31B···Cg1iv = 108°. Cg1 and Cg3 are the centroids of the N2/N3/C7—C9 imidazole rings and C12—C16/C25 anthraquinone rings]. Symmetry code for the two interactions, iii: 2 - x, 2 - y, 2 - z; iv: -x, 1 - y, 1 - z.