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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): m1285.
Published online 2009 October 3. doi:  10.1107/S1600536809039579
PMCID: PMC2971296

Bis[N′-(3-cyano­benzyl­idene)isonicotino­hydrazide-κN]silver(I) trifluoro­methane­sulfonate

Abstract

In the title compound, [Ag(C14H10N4O)2]CF3SO3, two N atoms from two independent pyridyl rings of two N′-3-cyano­benzyl­ideneisonicotinohydrazide ligands coordinate to the unique AgI ion, forming a nearly linear coordination geometry. Adjacent silver complexes are primarily linked together by Ag(...)N inter­actions, with Ag(...)N separations of 2.877 (2) and 3.314 (2) Å. On the other hand, one CF3SO3 anion inter­acts with hydrazone groups of two neighbouring ligands via N—H(...)O hydrogen bonds. These weak inter­molecular inter­actions contribute to the formation of supra­molecular chains. In addition, there are Ag(...)O inter­actions [2.787 (2) Å] between Ag and O atoms from adjacent chains.

Related literature

For the coordination of silver ions and properties of silver coordination compounds, see: Dong et al. (2004 [triangle]); Niu et al. (2008 [triangle], 2009 [triangle]); Sumby & Hardie (2005 [triangle]); Abu-Youssef et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-m1285-scheme1.jpg

Experimental

Crystal data

  • [Ag(C14H10N4O)2]CF3SO3
  • M r = 757.46
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1285-efi1.jpg
  • a = 7.5481 (17) Å
  • b = 14.164 (3) Å
  • c = 14.175 (3) Å
  • α = 87.895 (4)°
  • β = 89.918 (4)°
  • γ = 81.355 (4)°
  • V = 1497.2 (6) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.82 mm−1
  • T = 173 K
  • 0.32 × 0.22 × 0.17 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.780, T max = 0.874
  • 8251 measured reflections
  • 5461 independent reflections
  • 3857 reflections with I > 2σ(I)
  • R int = 0.023

Refinement

  • R[F 2 > 2σ(F 2)] = 0.060
  • wR(F 2) = 0.175
  • S = 1.03
  • 5461 reflections
  • 433 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 1.04 e Å−3
  • Δρmin = −0.87 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXL97 and DIAMOND (Brandenburg, 2005 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Selected geometric parameters (Å, °)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809039579/bh2248sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039579/bh2248Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We are grateful to Mrs Li (Wuhan University) for her assistance with the X-ray crystallographic analysis.

supplementary crystallographic information

Comment

In the title compound, (I), the silver(I) ion is coordinated by two nitrogen atoms from two independent pyridyl rings of two different ligands, forming a slightly distorted linear coordination geometry (Fig. 1). Related bond distances and angle around the metal center are shown in Table 1.

There are N—H···O hydrogen bonds between hydrazone groups from 3-cyanobenzylidene isonicotinohydrazide and counteranions CF3SO3- (Table 2). Besides, there are weak Ag···N interactions between two neighbouring silver complexes with separations of 2.877 (2) and 3.314 (2) Å. Hydrogen bonds and Ag···N interactions link parallel silver monomers together to construct interesting supramolecular one-dimensional chains. Furthermore, two adjacent supramolecular one-dimensional chains are linked together via Ag···O interactions, with the separation of 2.787 (2) Å (Fig. 2). All these intermolecular interactions have the contribution to the three-dimensional structure of the title compound.

It is noteworthy that the coordination geometry of the silver metal center can be affected by many factors, such as coordination natures of organic ligands, temperature, counteranions, etc. (Dong et al., 2004; Niu et al., 2009; Sumby & Hardie, 2005; Abu-Youssef et al., 2007). We have reported a Ag(I) polymeric structure recently (Niu et al., 2008), which includes a ligand isomeric to the one used in this paper (3-cyanobenzylidene isonicotinohydrazide). It showed that the position of the CN functional group seems to have a great influence on the structures of the resulting compounds (monomeric versus polymeric).

Experimental

A solution of AgCF3SO3 (0.026 g, 0.1 mmol) in CH3OH (10 ml) was carefully layered on a CH3OH/CHCl3 solution (5 ml/10 ml) of 3-cyanobenzylidene isonicotinohydrazide (0.025 g, 0.1 mmol) in a straight glass tube. About ten days later, colourless single crystals suitable for X-ray analysis were obtained.

Refinement

C-bound H atoms were placed in calculated positions and refined using a riding model [C—H = 0.95 Å and Uiso(H) = 1.2Ueq(C)]. The N-bound H atoms were first introduced in calculated positions and refined freely with Uiso(H) = 1.2Ueq(carrier N). The final difference Fourier map had a highest peak at 0.76 Å from atom H24 and a deepest hole at 0.64 Å from atom S3, but was otherwise featureless.

Figures

Fig. 1.
A view of the AgI coordination environment in the monomeric structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
Packing diagram showing three intermolecular interactions: hydrogen bonds are indicated by blue dashed lines, Ag···N interactions by red dashed lines, and Ag···O interactions by green dashed lines.

Crystal data

[Ag(C14H10N4O)2]CF3SO3Z = 2
Mr = 757.46F(000) = 760
Triclinic, P1Dx = 1.680 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.5481 (17) ÅCell parameters from 2331 reflections
b = 14.164 (3) Åθ = 2.0–25.5°
c = 14.175 (3) ŵ = 0.82 mm1
α = 87.895 (4)°T = 173 K
β = 89.918 (4)°Needle, yellow
γ = 81.355 (4)°0.32 × 0.22 × 0.17 mm
V = 1497.2 (6) Å3

Data collection

Bruker APEXII CCD area-detector diffractometer5461 independent reflections
Radiation source: fine-focus sealed tube3857 reflections with I > 2σ(I)
graphiteRint = 0.023
[var phi] and ω scansθmax = 25.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −8→9
Tmin = 0.780, Tmax = 0.874k = −15→17
8251 measured reflectionsl = −15→17

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.175H atoms treated by a mixture of independent and constrained refinement
S = 1.03w = 1/[σ2(Fo2) + (0.0934P)2 + 1.7184P] where P = (Fo2 + 2Fc2)/3
5461 reflections(Δ/σ)max < 0.001
433 parametersΔρmax = 1.04 e Å3
0 restraintsΔρmin = −0.87 e Å3
0 constraints

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

xyzUiso*/Ueq
Ag10.93777 (7)0.21340 (3)0.17729 (3)0.0685 (2)
N10.8202 (6)0.1314 (3)0.0743 (3)0.0514 (11)
N20.5612 (6)−0.0094 (4)−0.2091 (3)0.0513 (11)
N30.5110 (6)−0.0664 (3)−0.2783 (3)0.0521 (11)
N40.0251 (8)0.0449 (4)−0.7023 (4)0.0721 (14)
N51.0223 (6)0.3075 (3)0.2790 (3)0.0537 (11)
N61.2968 (6)0.4563 (4)0.5530 (3)0.0513 (11)
N71.3579 (6)0.5147 (3)0.6166 (3)0.0505 (10)
N81.8445 (9)0.4103 (5)1.0418 (4)0.0814 (16)
O10.7156 (6)−0.1358 (3)−0.1262 (3)0.0635 (11)
O21.2202 (6)0.5775 (3)0.4444 (3)0.0660 (11)
O30.2036 (7)0.2847 (3)0.6588 (3)0.0823 (14)
O40.1417 (11)0.1451 (4)0.7472 (4)0.120 (2)
O50.4103 (8)0.2082 (5)0.7702 (4)0.124 (2)
S30.2325 (3)0.22699 (11)0.74187 (11)0.0677 (5)
F1−0.0500 (8)0.3171 (5)0.8159 (4)0.135 (2)
F20.1803 (8)0.3828 (3)0.8371 (3)0.1131 (17)
F30.1446 (7)0.2578 (3)0.9181 (3)0.0987 (14)
C10.8156 (7)0.0385 (4)0.0907 (4)0.0512 (13)
H10.85080.01150.15130.061*
C20.7630 (7)−0.0201 (4)0.0248 (4)0.0498 (12)
H20.7614−0.08590.03980.060*
C30.7118 (6)0.0181 (4)−0.0644 (3)0.0425 (11)
C40.7153 (9)0.1136 (4)−0.0820 (4)0.0589 (15)
H40.68110.1424−0.14220.071*
C50.7688 (9)0.1674 (4)−0.0114 (4)0.0617 (15)
H50.76930.2336−0.02430.074*
C60.6637 (7)−0.0506 (4)−0.1360 (4)0.0471 (12)
C70.4229 (7)−0.0216 (4)−0.3474 (4)0.0524 (13)
H70.40100.0463−0.34880.063*
C80.3555 (7)−0.0722 (4)−0.4237 (3)0.0473 (12)
C90.3767 (9)−0.1707 (4)−0.4261 (4)0.0662 (16)
H90.4402−0.2080−0.37650.079*
C100.3077 (11)−0.2158 (5)−0.4991 (5)0.082 (2)
H100.3247−0.2836−0.49970.098*
C110.2132 (10)−0.1621 (5)−0.5717 (5)0.0746 (19)
H110.1631−0.1929−0.62140.089*
C120.1925 (8)−0.0643 (4)−0.5713 (4)0.0559 (14)
C130.2621 (7)−0.0184 (4)−0.4967 (3)0.0484 (12)
H130.24540.0494−0.49620.058*
C140.0978 (8)−0.0051 (5)−0.6452 (4)0.0572 (14)
C151.0095 (7)0.4007 (4)0.2630 (4)0.0520 (13)
H150.95260.42750.20640.062*
C161.0737 (7)0.4608 (4)0.3233 (4)0.0495 (12)
H161.06170.52730.30790.059*
C171.1562 (7)0.4243 (4)0.4069 (3)0.0442 (11)
C181.1695 (10)0.3279 (4)0.4243 (4)0.0723 (19)
H181.22290.29980.48130.087*
C191.1061 (11)0.2720 (4)0.3597 (5)0.078 (2)
H191.12160.20480.37210.093*
C201.2263 (7)0.4947 (4)0.4696 (4)0.0477 (12)
C211.4326 (7)0.4693 (4)0.6902 (4)0.0510 (13)
H211.44250.40160.69540.061*
C221.5024 (7)0.5212 (4)0.7661 (4)0.0490 (12)
C231.4820 (8)0.6210 (4)0.7655 (4)0.0575 (14)
H231.41700.65760.71580.069*
C241.5556 (9)0.6667 (4)0.8366 (4)0.0648 (16)
H241.54030.73450.83640.078*
C251.6511 (8)0.6137 (4)0.9077 (4)0.0615 (15)
H251.70580.64510.95530.074*
C261.6686 (7)0.5153 (4)0.9106 (4)0.0535 (13)
C271.5949 (7)0.4690 (4)0.8391 (4)0.0504 (12)
H271.60820.40120.84060.060*
C281.7683 (8)0.4570 (4)0.9849 (4)0.0581 (14)
C290.1274 (11)0.2994 (4)0.8338 (5)0.0696 (17)
H281.287 (7)0.397 (4)0.575 (4)0.047 (15)*
H290.529 (8)0.051 (4)−0.217 (4)0.055 (17)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ag10.0727 (4)0.0744 (4)0.0628 (3)−0.0187 (2)−0.0167 (2)−0.0289 (2)
N10.053 (3)0.052 (3)0.052 (3)−0.012 (2)−0.017 (2)−0.010 (2)
N20.056 (3)0.053 (3)0.044 (2)−0.004 (2)−0.014 (2)−0.015 (2)
N30.054 (3)0.058 (3)0.045 (2)−0.010 (2)−0.011 (2)−0.017 (2)
N40.074 (4)0.091 (4)0.055 (3)−0.024 (3)−0.020 (3)0.005 (3)
N50.064 (3)0.052 (3)0.046 (2)−0.010 (2)−0.015 (2)−0.009 (2)
N60.062 (3)0.053 (3)0.041 (2)−0.014 (2)−0.018 (2)−0.006 (2)
N70.051 (3)0.060 (3)0.042 (2)−0.013 (2)−0.0110 (19)−0.009 (2)
N80.093 (4)0.094 (4)0.059 (3)−0.016 (3)−0.029 (3)−0.005 (3)
O10.079 (3)0.049 (2)0.064 (2)−0.013 (2)−0.029 (2)−0.0073 (18)
O20.090 (3)0.051 (2)0.059 (2)−0.014 (2)−0.028 (2)−0.0045 (19)
O30.120 (4)0.075 (3)0.053 (3)−0.018 (3)−0.009 (2)0.007 (2)
O40.200 (7)0.061 (3)0.108 (4)−0.045 (4)0.000 (4)−0.006 (3)
O50.091 (4)0.168 (6)0.099 (4)0.032 (4)−0.022 (3)−0.007 (4)
S30.0903 (12)0.0504 (8)0.0573 (9)0.0049 (8)−0.0142 (8)0.0033 (7)
F10.096 (4)0.161 (5)0.134 (5)0.022 (4)0.016 (3)0.014 (4)
F20.199 (6)0.058 (2)0.087 (3)−0.033 (3)0.010 (3)−0.016 (2)
F30.163 (4)0.074 (2)0.055 (2)−0.009 (3)−0.002 (2)0.0057 (19)
C10.053 (3)0.061 (3)0.040 (3)−0.013 (3)−0.015 (2)0.000 (2)
C20.056 (3)0.044 (3)0.050 (3)−0.012 (2)−0.014 (2)0.004 (2)
C30.039 (3)0.050 (3)0.040 (3)−0.012 (2)−0.011 (2)−0.002 (2)
C40.082 (4)0.049 (3)0.046 (3)−0.013 (3)−0.027 (3)0.004 (2)
C50.082 (4)0.046 (3)0.058 (3)−0.014 (3)−0.028 (3)0.002 (3)
C60.045 (3)0.052 (3)0.045 (3)−0.009 (2)−0.014 (2)−0.004 (2)
C70.054 (3)0.058 (3)0.044 (3)−0.004 (3)−0.013 (2)−0.010 (2)
C80.047 (3)0.056 (3)0.040 (3)−0.009 (2)−0.010 (2)−0.006 (2)
C90.079 (4)0.055 (3)0.066 (4)−0.015 (3)−0.029 (3)0.000 (3)
C100.102 (5)0.058 (4)0.088 (5)−0.016 (4)−0.037 (4)−0.009 (3)
C110.089 (5)0.073 (4)0.066 (4)−0.023 (4)−0.033 (3)−0.013 (3)
C120.058 (3)0.069 (4)0.045 (3)−0.021 (3)−0.012 (2)−0.008 (3)
C130.053 (3)0.054 (3)0.040 (3)−0.011 (2)−0.009 (2)−0.008 (2)
C140.057 (3)0.074 (4)0.044 (3)−0.023 (3)−0.013 (3)−0.004 (3)
C150.054 (3)0.063 (3)0.038 (3)−0.004 (3)−0.020 (2)−0.009 (2)
C160.056 (3)0.047 (3)0.045 (3)−0.005 (2)−0.015 (2)0.001 (2)
C170.049 (3)0.054 (3)0.029 (2)−0.006 (2)−0.006 (2)−0.004 (2)
C180.115 (6)0.051 (3)0.050 (3)−0.013 (3)−0.037 (3)0.006 (3)
C190.131 (6)0.043 (3)0.061 (4)−0.017 (3)−0.044 (4)−0.001 (3)
C200.047 (3)0.047 (3)0.048 (3)−0.004 (2)−0.010 (2)−0.008 (2)
C210.058 (3)0.058 (3)0.041 (3)−0.018 (3)−0.010 (2)−0.005 (2)
C220.048 (3)0.057 (3)0.043 (3)−0.013 (2)−0.015 (2)−0.003 (2)
C230.057 (3)0.059 (3)0.057 (3)−0.010 (3)−0.010 (3)−0.001 (3)
C240.077 (4)0.053 (3)0.067 (4)−0.015 (3)−0.009 (3)−0.012 (3)
C250.062 (4)0.070 (4)0.057 (3)−0.019 (3)−0.015 (3)−0.019 (3)
C260.051 (3)0.067 (4)0.044 (3)−0.012 (3)−0.010 (2)−0.011 (3)
C270.056 (3)0.053 (3)0.043 (3)−0.012 (2)−0.009 (2)−0.006 (2)
C280.059 (4)0.073 (4)0.044 (3)−0.012 (3)−0.013 (3)−0.009 (3)
C290.098 (5)0.047 (3)0.060 (4)0.000 (3)−0.015 (3)0.008 (3)

Geometric parameters (Å, °)

Ag1—N52.160 (4)C7—H70.9500
Ag1—N12.169 (4)C8—C91.381 (8)
N1—C11.333 (7)C8—C131.390 (7)
N1—C51.335 (7)C9—C101.379 (8)
N2—C61.354 (7)C9—H90.9500
N2—N31.381 (6)C10—C111.389 (9)
N2—H290.86 (6)C10—H100.9500
N3—C71.278 (7)C11—C121.370 (9)
N4—C141.140 (7)C11—H110.9500
N5—C151.320 (7)C12—C131.404 (7)
N5—C191.351 (8)C12—C141.439 (8)
N6—C201.359 (7)C13—H130.9500
N6—N71.371 (6)C15—C161.366 (7)
N6—H280.90 (5)C15—H150.9500
N7—C211.291 (7)C16—C171.386 (7)
N8—C281.126 (8)C16—H160.9500
O1—C61.215 (6)C17—C181.368 (8)
O2—C201.207 (6)C17—C201.513 (7)
O3—S31.407 (4)C18—C191.365 (8)
O4—S31.432 (6)C18—H180.9500
O5—S31.385 (6)C19—H190.9500
S3—C291.798 (7)C21—C221.467 (7)
F1—C291.347 (9)C21—H210.9500
F2—C291.305 (8)C22—C271.377 (7)
F3—C291.310 (7)C22—C231.399 (8)
C1—C21.371 (7)C23—C241.379 (8)
C1—H10.9500C23—H230.9500
C2—C31.389 (7)C24—C251.371 (9)
C2—H20.9500C24—H240.9500
C3—C41.371 (7)C25—C261.380 (8)
C3—C61.514 (7)C25—H250.9500
C4—C51.377 (7)C26—C271.389 (7)
C4—H40.9500C26—C281.452 (8)
C5—H50.9500C27—H270.9500
C7—C81.453 (7)
N5—Ag1—N1172.56 (17)C11—C12—C13120.4 (5)
C1—N1—C5116.7 (4)C11—C12—C14122.0 (5)
C1—N1—Ag1120.4 (3)C13—C12—C14117.6 (5)
C5—N1—Ag1122.4 (4)C8—C13—C12119.9 (5)
C6—N2—N3119.1 (5)C8—C13—H13120.0
C6—N2—H29124 (4)C12—C13—H13120.0
N3—N2—H29116 (4)N4—C14—C12177.3 (6)
C7—N3—N2115.2 (5)N5—C15—C16123.6 (5)
C15—N5—C19116.4 (5)N5—C15—H15118.2
C15—N5—Ag1122.6 (3)C16—C15—H15118.2
C19—N5—Ag1120.7 (4)C15—C16—C17119.8 (5)
C20—N6—N7119.2 (5)C15—C16—H16120.1
C20—N6—H28124 (4)C17—C16—H16120.1
N7—N6—H28116 (4)C18—C17—C16117.0 (5)
C21—N7—N6113.5 (4)C18—C17—C20126.1 (5)
O5—S3—O3113.8 (4)C16—C17—C20116.9 (4)
O5—S3—O4114.0 (4)C19—C18—C17120.0 (5)
O3—S3—O4115.9 (3)C19—C18—H18120.0
O5—S3—C29103.2 (4)C17—C18—H18120.0
O3—S3—C29105.1 (3)N5—C19—C18123.1 (5)
O4—S3—C29102.8 (4)N5—C19—H19118.4
N1—C1—C2123.6 (5)C18—C19—H19118.4
N1—C1—H1118.2O2—C20—N6124.5 (5)
C2—C1—H1118.2O2—C20—C17120.9 (5)
C1—C2—C3118.9 (5)N6—C20—C17114.5 (4)
C1—C2—H2120.5N7—C21—C22120.6 (5)
C3—C2—H2120.5N7—C21—H21119.7
C4—C3—C2118.1 (5)C22—C21—H21119.7
C4—C3—C6125.1 (4)C27—C22—C23119.4 (5)
C2—C3—C6116.8 (4)C27—C22—C21118.2 (5)
C3—C4—C5119.1 (5)C23—C22—C21122.4 (5)
C3—C4—H4120.5C24—C23—C22120.3 (6)
C5—C4—H4120.5C24—C23—H23119.8
N1—C5—C4123.6 (5)C22—C23—H23119.8
N1—C5—H5118.2C25—C24—C23119.7 (6)
C4—C5—H5118.2C25—C24—H24120.2
O1—C6—N2124.3 (5)C23—C24—H24120.2
O1—C6—C3120.7 (4)C24—C25—C26120.7 (5)
N2—C6—C3114.9 (4)C24—C25—H25119.7
N3—C7—C8121.4 (5)C26—C25—H25119.7
N3—C7—H7119.3C25—C26—C27119.8 (5)
C8—C7—H7119.3C25—C26—C28122.2 (5)
C9—C8—C13118.7 (5)C27—C26—C28118.0 (5)
C9—C8—C7123.2 (5)C22—C27—C26120.1 (5)
C13—C8—C7118.0 (5)C22—C27—H27120.0
C10—C9—C8121.4 (6)C26—C27—H27120.0
C10—C9—H9119.3N8—C28—C26178.7 (6)
C8—C9—H9119.3F2—C29—F3108.7 (6)
C9—C10—C11119.9 (6)F2—C29—F1106.0 (6)
C9—C10—H10120.0F3—C29—F1106.0 (6)
C11—C10—H10120.0F2—C29—S3113.5 (5)
C12—C11—C10119.6 (5)F3—C29—S3113.9 (4)
C12—C11—H11120.2F1—C29—S3108.1 (5)
C10—C11—H11120.2
C6—N2—N3—C7−176.3 (5)C15—C16—C17—C20179.1 (5)
C20—N6—N7—C21−175.6 (5)C16—C17—C18—C191.3 (10)
C5—N1—C1—C20.4 (8)C20—C17—C18—C19−177.5 (6)
Ag1—N1—C1—C2−172.1 (4)C15—N5—C19—C182.4 (11)
N1—C1—C2—C30.3 (8)Ag1—N5—C19—C18176.9 (6)
C1—C2—C3—C4−0.5 (8)C17—C18—C19—N5−2.7 (12)
C1—C2—C3—C6177.1 (5)N7—N6—C20—O23.5 (8)
C2—C3—C4—C50.1 (9)N7—N6—C20—C17−177.5 (4)
C6—C3—C4—C5−177.3 (5)C18—C17—C20—O2174.2 (6)
C1—N1—C5—C4−0.9 (9)C16—C17—C20—O2−4.5 (8)
Ag1—N1—C5—C4171.4 (5)C18—C17—C20—N6−4.8 (8)
C3—C4—C5—N10.7 (10)C16—C17—C20—N6176.4 (5)
N3—N2—C6—O1−0.2 (8)N6—N7—C21—C22−178.9 (5)
N3—N2—C6—C3179.8 (4)N7—C21—C22—C27−174.4 (5)
C4—C3—C6—O1156.7 (6)N7—C21—C22—C234.1 (8)
C2—C3—C6—O1−20.7 (8)C27—C22—C23—C240.8 (9)
C4—C3—C6—N2−23.3 (8)C21—C22—C23—C24−177.6 (5)
C2—C3—C6—N2159.3 (5)C22—C23—C24—C250.8 (9)
N2—N3—C7—C8−177.8 (5)C23—C24—C25—C26−2.4 (10)
N3—C7—C8—C91.9 (9)C24—C25—C26—C272.5 (9)
N3—C7—C8—C13−179.5 (5)C24—C25—C26—C28−179.8 (6)
C13—C8—C9—C100.1 (10)C23—C22—C27—C26−0.8 (8)
C7—C8—C9—C10178.7 (6)C21—C22—C27—C26177.7 (5)
C8—C9—C10—C11−0.6 (12)C25—C26—C27—C22−0.9 (8)
C9—C10—C11—C121.4 (12)C28—C26—C27—C22−178.6 (5)
C10—C11—C12—C13−1.7 (10)O5—S3—C29—F266.4 (6)
C10—C11—C12—C14179.2 (7)O3—S3—C29—F2−53.2 (6)
C9—C8—C13—C12−0.4 (8)O4—S3—C29—F2−174.8 (5)
C7—C8—C13—C12−179.1 (5)O5—S3—C29—F3−58.8 (7)
C11—C12—C13—C81.2 (9)O3—S3—C29—F3−178.3 (5)
C14—C12—C13—C8−179.6 (5)O4—S3—C29—F360.0 (7)
C19—N5—C15—C16−0.8 (9)O5—S3—C29—F1−176.3 (5)
Ag1—N5—C15—C16−175.2 (4)O3—S3—C29—F164.1 (6)
N5—C15—C16—C17−0.5 (9)O4—S3—C29—F1−57.6 (6)
C15—C16—C17—C180.3 (8)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H29···O5i0.86 (6)2.27 (6)3.125 (9)173 (5)
N6—H28···O3ii0.90 (5)2.12 (6)2.982 (7)161 (5)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2248).

References

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