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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2011 Aug 27;67(Pt 9):m1316. doi: 10.1107/S160053681103385X

{meso-Tetra­kis[p-(hept­yloxy)phen­yl]­porphyrinato}silver(II)

Jun-Xu Liao a,b, Hong-Bin Zhao a,c,*, De-Liang Yang c, Liang Chen c, Bang-Ying Wang c
PMCID: PMC3200905  PMID: 22065718

Abstract

The title compound, [Ag(C72H84N4O4)], crystallizes with the AgII cation on a centre of symmetry. The macrocyclic 24-membered ring core is planar with a mean deviation of 0.0311 (15) Å and the four-coordinate AgII cation fits into its center, at 2.0814 (19) and 2.0872 (19) Å, from the surrounding pyrrole-N atoms, in agreement with what is found in related compounds. The p-heptyl­oxyphenyl groups are rotated 75.51 (5) and 84.45 (8)° with respect to the porphyrin mean plane, due to steric hindrance with the pyrrole-H atoms of the macrocycle.

Related literature

For background information on metalloporphyrins and their derivatives, see: Fu et al. (2009 ▶); Jurow et al. (2010 ▶); Taniguchi & Lindsey (2010 ▶); Zenkevich et al. (2001 ▶). For related structures, see: Scheidt et al. (1986 ▶); Xu et al. (2007 ▶).graphic file with name e-67-m1316-scheme1.jpg

Experimental

Crystal data

  • [Ag(C72H84N4O4)]

  • M r = 1177.30

  • Monoclinic, Inline graphic

  • a = 15.850 (1) Å

  • b = 19.1896 (12) Å

  • c = 10.3285 (7) Å

  • β = 91.724 (1)°

  • V = 3140.0 (4) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.37 mm−1

  • T = 185 K

  • 0.24 × 0.17 × 0.10 mm

Data collection

  • Bruker APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.916, T max = 0.964

  • 18310 measured reflections

  • 5544 independent reflections

  • 4385 reflections with I > 2σ(I)

  • R int = 0.035

Refinement

  • R[F 2 > 2σ(F 2)] = 0.036

  • wR(F 2) = 0.091

  • S = 1.02

  • 5544 reflections

  • 369 parameters

  • H-atom parameters constrained

  • Δρmax = 0.53 e Å−3

  • Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and PLATON (Spek, 2009 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681103385X/bg2416sup1.cif

e-67-m1316-sup1.cif (25.4KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681103385X/bg2416Isup2.hkl

e-67-m1316-Isup2.hkl (271.5KB, hkl)

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

Acknowledgments

This work was supported by the National Analytical Research Center of Electrochemistry and Spectroscopy, Changchun Institute of Applied Chemistry, Changchun, China.

supplementary crystallographic information

Comment

Porphyrins, metalloporphyrins, and their derivatives are applied in many fields, such as biomimetic catalysts (Fu et al., 2009), molecular electronic components (Jurow et al., 2010), artificial photosynthesis (Taniguchi et al., 2010) or electron transfer and energy migration (Zenkevich et al., 2001). In this paper, the structure of Silver(II)meso-tetrakis[p-(heptyloxy)phenyl]porphyrinate (I) is reported.

The compound crystallizes with the AgII cation in a centre of symmetry (Fig. 1). The macrocyclic 24-membered ring core is planar with a mean deviation of 0.0311 (15) Å and the four coordinate AgII ion fits into its center, at 2.0814 (19) and 2.0872 (19) Å, from the surrouding pyrrole N atoms, in agreement with what found in related compounds (Scheidt et al., 1986; Xu et al., 2007).

The p-heptyloxyphenyl groups are rotated at angles of 75.51 (5)° and 84.45 (8)° with respect to the porphyrin mean plane, due to steric hindrance with the pyrrole-H atoms of the macrocycle.

Experimental

0.03mmol meso-tetrakis[p-(heptyloxy)phenyl] porphyrin and 0.06mmol AgNO3 were dissolved in 20 ml chloroform, refluxed for 6 hours, and the solvent was removed by a rotary evaporator, the residue was purified by column chromatography with chloroform, then recrystallized from a methanol/chloroform solution, and a purple solid was obtained (yield=23%). Single crystals were obtained from recrystallization from a dichloromethane solution at room temperature.

Refinement

H atoms were placed in calculated positions (C—H = 0.95, 0.98 or 0.99 Å) and refined in riding mode, with Uiso(H) = xUeq(C), where x = 1.5 for methyl and 1.2 for all other H atoms.

A Platon run (Spek, 2009) detects solvent accessible voids of 78 Å3, which indicate that the structure may contain disordered solvent molecules (dichloromethane). However, efforts to locate the solvent molecules failed because the residual electron density is small (the highest peak of residual density is 0.529 e Å-3).

Figures

Fig. 1.

Fig. 1.

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A view of (I), with the atom-labeling scheme and 50% probability displacement ellipsoids. Symmetry codes: (i) -x, -y, -z+2.

Crystal data

[Ag(C72H84N4O4)] F(000) = 1246
Mr = 1177.30 Dx = 1.245 Mg m−3
Monoclinic, P21/c Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc Cell parameters from 5112 reflections
a = 15.850 (1) Å θ = 2.2–24.8°
b = 19.1896 (12) Å µ = 0.37 mm−1
c = 10.3285 (7) Å T = 185 K
β = 91.724 (1)° Block, purple
V = 3140.0 (4) Å3 0.24 × 0.17 × 0.10 mm
Z = 2
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Data collection

Bruker APEX CCD diffractometer 5544 independent reflections
Radiation source: fine-focus sealed tube 4385 reflections with I > 2σ(I)
graphite Rint = 0.035
φ and ω scans θmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) h = −17→18
Tmin = 0.916, Tmax = 0.964 k = −22→19
18310 measured reflections l = −12→12
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Refinement

Refinement on F2 Primary atom site location: structure-invariant direct methods
Least-squares matrix: full Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091 H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0483P)2 + 0.7718P] where P = (Fo2 + 2Fc2)/3
5544 reflections (Δ/σ)max < 0.001
369 parameters Δρmax = 0.53 e Å−3
0 restraints Δρmin = −0.20 e Å−3
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Special details

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

x y z Uiso*/Ueq
Ag1 0.0000 0.0000 1.0000 0.02274 (9)
C1 −0.17114 (15) 0.03711 (13) 1.1183 (2) 0.0268 (6)
C2 −0.22273 (16) 0.09570 (13) 1.1505 (2) 0.0307 (6)
H2 −0.2766 0.0938 1.1884 0.037*
C3 −0.18104 (16) 0.15392 (14) 1.1173 (2) 0.0302 (6)
H3 −0.2003 0.2004 1.1272 0.036*
C4 −0.10181 (15) 0.13291 (13) 1.0637 (2) 0.0267 (6)
C5 −0.03796 (16) 0.17749 (12) 1.0229 (2) 0.0242 (5)
C6 −0.05259 (15) 0.25455 (12) 1.0355 (2) 0.0254 (5)
C7 −0.10737 (17) 0.29051 (14) 0.9522 (2) 0.0347 (6)
H7 −0.1365 0.2661 0.8845 0.042*
C8 −0.12023 (17) 0.36174 (14) 0.9664 (2) 0.0353 (6)
H8 −0.1582 0.3854 0.9087 0.042*
C9 −0.07828 (16) 0.39834 (13) 1.0637 (2) 0.0284 (6)
C10 −0.02294 (18) 0.36346 (14) 1.1466 (2) 0.0361 (7)
H10 0.0069 0.3880 1.2134 0.043*
C11 −0.01107 (18) 0.29203 (13) 1.1314 (2) 0.0354 (6)
H11 0.0269 0.2684 1.1892 0.042*
C12 −0.04960 (18) 0.50778 (12) 1.1669 (3) 0.0341 (6)
H12A 0.0109 0.5097 1.1459 0.041*
H12B −0.0545 0.4855 1.2528 0.041*
C13 −0.08601 (17) 0.58049 (13) 1.1696 (3) 0.0339 (6)
H13A −0.0896 0.5991 1.0802 0.041*
H13B −0.0476 0.6110 1.2214 0.041*
C14 −0.17338 (17) 0.58243 (13) 1.2270 (3) 0.0337 (6)
H14A −0.2116 0.5524 1.1739 0.040*
H14B −0.1696 0.5623 1.3153 0.040*
C15 −0.21219 (17) 0.65466 (14) 1.2351 (3) 0.0350 (6)
H15A −0.2249 0.6720 1.1463 0.042*
H15B −0.1707 0.6868 1.2765 0.042*
C16 −0.29271 (18) 0.65544 (14) 1.3115 (3) 0.0383 (7)
H16A −0.3327 0.6213 1.2724 0.046*
H16B −0.2790 0.6399 1.4011 0.046*
C17 −0.3360 (2) 0.72544 (17) 1.3171 (3) 0.0521 (8)
H17A −0.3525 0.7400 1.2280 0.062*
H17B −0.2954 0.7603 1.3527 0.062*
C18 −0.4137 (2) 0.72520 (19) 1.3994 (4) 0.0679 (10)
H18A −0.4538 0.6902 1.3659 0.102*
H18B −0.4403 0.7713 1.3961 0.102*
H18C −0.3973 0.7139 1.4892 0.102*
C19 0.04070 (16) 0.15704 (12) 0.9737 (2) 0.0240 (5)
C20 0.10418 (16) 0.20316 (13) 0.9264 (2) 0.0291 (6)
H20 0.1026 0.2526 0.9284 0.035*
C21 0.16623 (16) 0.16374 (13) 0.8789 (2) 0.0281 (6)
H21 0.2160 0.1804 0.8402 0.034*
C22 0.14361 (15) 0.09178 (13) 0.8972 (2) 0.0253 (6)
C23 0.19112 (15) 0.03383 (14) 0.8601 (2) 0.0264 (6)
C24 0.26926 (16) 0.04802 (13) 0.7844 (2) 0.0284 (6)
C25 0.26415 (17) 0.04737 (15) 0.6514 (3) 0.0379 (7)
H25 0.2115 0.0372 0.6092 0.045*
C26 0.33407 (17) 0.06126 (15) 0.5767 (3) 0.0397 (7)
H26 0.3292 0.0597 0.4849 0.048*
C27 0.41000 (17) 0.07728 (13) 0.6369 (3) 0.0326 (6)
C28 0.41643 (17) 0.07760 (16) 0.7708 (3) 0.0428 (7)
H28 0.4690 0.0880 0.8130 0.051*
C29 0.34655 (17) 0.06290 (15) 0.8436 (3) 0.0388 (7)
H29 0.3519 0.0630 0.9354 0.047*
C30 0.47894 (19) 0.09010 (16) 0.4349 (3) 0.0432 (7)
H30A 0.4315 0.1190 0.4008 0.052*
H30B 0.4693 0.0414 0.4062 0.052*
C31 0.56106 (19) 0.11666 (15) 0.3838 (3) 0.0466 (8)
H31A 0.5638 0.1047 0.2907 0.056*
H31B 0.6084 0.0927 0.4298 0.056*
C32 0.57217 (18) 0.19524 (15) 0.3996 (3) 0.0431 (7)
H32A 0.5192 0.2186 0.3707 0.052*
H32B 0.5817 0.2059 0.4927 0.052*
C33 0.64472 (18) 0.22525 (15) 0.3246 (3) 0.0437 (7)
H33A 0.6986 0.2064 0.3608 0.052*
H33B 0.6390 0.2100 0.2331 0.052*
C34 0.6478 (2) 0.30437 (16) 0.3290 (3) 0.0500 (8)
H34A 0.5923 0.3228 0.2990 0.060*
H34B 0.6573 0.3192 0.4201 0.060*
C35 0.7154 (2) 0.33636 (16) 0.2479 (4) 0.0569 (9)
H35A 0.7076 0.3200 0.1575 0.068*
H35B 0.7713 0.3198 0.2805 0.068*
C36 0.7149 (3) 0.41504 (18) 0.2490 (4) 0.0837 (13)
H36A 0.6608 0.4319 0.2128 0.126*
H36B 0.7609 0.4325 0.1967 0.126*
H36C 0.7225 0.4317 0.3383 0.126*
N1 −0.09901 (12) 0.06134 (10) 1.06458 (18) 0.0258 (5)
N2 0.06710 (12) 0.08969 (10) 0.95571 (18) 0.0236 (4)
O1 −0.09551 (11) 0.46820 (9) 1.07045 (16) 0.0327 (4)
O2 0.48278 (11) 0.09324 (10) 0.57368 (18) 0.0400 (5)
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
Ag1 0.02106 (15) 0.01858 (15) 0.02898 (14) 0.00032 (12) 0.00751 (10) 0.00036 (11)
C1 0.0219 (14) 0.0264 (15) 0.0324 (13) 0.0016 (11) 0.0069 (11) −0.0005 (11)
C2 0.0256 (14) 0.0273 (15) 0.0399 (14) 0.0000 (12) 0.0114 (11) −0.0009 (11)
C3 0.0270 (14) 0.0256 (14) 0.0386 (14) 0.0045 (12) 0.0089 (11) −0.0017 (11)
C4 0.0245 (14) 0.0254 (15) 0.0303 (13) 0.0028 (11) 0.0025 (10) −0.0006 (10)
C5 0.0265 (14) 0.0195 (13) 0.0267 (12) 0.0012 (11) 0.0036 (10) −0.0009 (10)
C6 0.0243 (13) 0.0210 (13) 0.0313 (13) 0.0003 (11) 0.0064 (10) 0.0012 (10)
C7 0.0372 (16) 0.0267 (15) 0.0399 (14) 0.0015 (12) −0.0061 (12) −0.0058 (12)
C8 0.0391 (16) 0.0251 (15) 0.0411 (15) 0.0078 (13) −0.0090 (12) 0.0004 (12)
C9 0.0327 (15) 0.0202 (13) 0.0326 (13) 0.0030 (11) 0.0063 (11) 0.0010 (11)
C10 0.0457 (17) 0.0268 (15) 0.0355 (14) 0.0032 (13) −0.0059 (12) −0.0079 (11)
C11 0.0447 (17) 0.0249 (15) 0.0361 (14) 0.0097 (13) −0.0060 (12) −0.0010 (11)
C12 0.0394 (16) 0.0235 (15) 0.0394 (14) 0.0003 (12) 0.0022 (12) −0.0067 (11)
C13 0.0379 (16) 0.0238 (15) 0.0404 (15) 0.0003 (12) 0.0055 (12) −0.0036 (11)
C14 0.0385 (16) 0.0241 (15) 0.0387 (14) −0.0030 (12) 0.0059 (12) −0.0013 (11)
C15 0.0376 (17) 0.0255 (15) 0.0423 (15) −0.0006 (13) 0.0102 (12) −0.0029 (12)
C16 0.0392 (17) 0.0338 (16) 0.0422 (15) −0.0006 (13) 0.0069 (13) −0.0012 (13)
C17 0.046 (2) 0.0436 (19) 0.067 (2) 0.0084 (16) 0.0201 (16) −0.0013 (16)
C18 0.067 (3) 0.059 (2) 0.080 (2) 0.015 (2) 0.036 (2) 0.0017 (19)
C19 0.0279 (14) 0.0190 (13) 0.0254 (12) −0.0008 (11) 0.0030 (10) −0.0001 (10)
C20 0.0293 (15) 0.0223 (14) 0.0360 (13) −0.0010 (12) 0.0052 (11) 0.0014 (11)
C21 0.0238 (14) 0.0250 (14) 0.0359 (14) −0.0045 (11) 0.0075 (11) 0.0039 (11)
C22 0.0239 (14) 0.0229 (14) 0.0294 (12) −0.0014 (11) 0.0038 (10) 0.0006 (10)
C23 0.0212 (14) 0.0285 (15) 0.0296 (13) −0.0007 (12) 0.0049 (10) −0.0015 (11)
C24 0.0266 (14) 0.0205 (14) 0.0387 (14) −0.0001 (11) 0.0092 (11) −0.0015 (11)
C25 0.0267 (15) 0.0478 (18) 0.0393 (15) −0.0075 (13) 0.0039 (12) 0.0008 (13)
C26 0.0344 (16) 0.0507 (19) 0.0345 (14) −0.0066 (14) 0.0078 (12) 0.0040 (13)
C27 0.0293 (15) 0.0251 (15) 0.0441 (15) −0.0008 (12) 0.0146 (12) −0.0003 (12)
C28 0.0251 (15) 0.055 (2) 0.0480 (16) −0.0101 (14) 0.0058 (12) −0.0047 (14)
C29 0.0316 (16) 0.0503 (19) 0.0350 (14) −0.0076 (14) 0.0072 (12) −0.0063 (13)
C30 0.0437 (18) 0.0407 (18) 0.0463 (16) −0.0043 (15) 0.0211 (14) 0.0019 (14)
C31 0.0451 (19) 0.0381 (18) 0.0581 (18) 0.0015 (15) 0.0265 (15) 0.0034 (15)
C32 0.0376 (17) 0.0376 (17) 0.0551 (17) 0.0015 (14) 0.0189 (14) 0.0007 (14)
C33 0.0329 (16) 0.0355 (17) 0.0637 (19) 0.0010 (14) 0.0175 (14) 0.0060 (14)
C34 0.047 (2) 0.0381 (18) 0.066 (2) −0.0011 (15) 0.0148 (16) 0.0048 (15)
C35 0.046 (2) 0.0369 (19) 0.088 (2) −0.0063 (16) 0.0157 (18) 0.0155 (17)
C36 0.083 (3) 0.040 (2) 0.130 (4) −0.014 (2) 0.035 (3) 0.011 (2)
N1 0.0238 (11) 0.0196 (11) 0.0346 (11) 0.0014 (9) 0.0092 (9) 0.0005 (9)
N2 0.0214 (11) 0.0199 (11) 0.0300 (10) 0.0016 (9) 0.0071 (8) 0.0000 (8)
O1 0.0418 (12) 0.0206 (9) 0.0355 (10) 0.0054 (8) −0.0016 (8) −0.0037 (8)
O2 0.0299 (11) 0.0412 (12) 0.0499 (11) −0.0050 (9) 0.0179 (9) 0.0035 (9)
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Geometric parameters (Å, °)

Ag1—N2 2.0814 (19) C18—H18B 0.9800
Ag1—N2i 2.0815 (19) C18—H18C 0.9800
Ag1—N1i 2.0871 (19) C19—N2 1.373 (3)
Ag1—N1 2.0872 (19) C19—C20 1.436 (3)
C1—N1 1.367 (3) C20—C21 1.345 (3)
C1—C23i 1.417 (4) C20—H20 0.9500
C1—C2 1.435 (3) C21—C22 1.441 (3)
C2—C3 1.348 (3) C21—H21 0.9500
C2—H2 0.9500 C22—N2 1.371 (3)
C3—C4 1.445 (3) C22—C23 1.403 (3)
C3—H3 0.9500 C23—C1i 1.417 (4)
C4—N1 1.374 (3) C23—C24 1.509 (3)
C4—C5 1.400 (3) C24—C25 1.373 (3)
C5—C19 1.416 (3) C24—C29 1.382 (4)
C5—C6 1.503 (3) C25—C26 1.395 (3)
C6—C11 1.376 (3) C25—H25 0.9500
C6—C7 1.387 (3) C26—C27 1.372 (4)
C7—C8 1.390 (4) C26—H26 0.9500
C7—H7 0.9500 C27—O2 1.377 (3)
C8—C9 1.380 (3) C27—C28 1.384 (4)
C8—H8 0.9500 C28—C29 1.386 (4)
C9—O1 1.370 (3) C28—H28 0.9500
C9—C10 1.380 (3) C29—H29 0.9500
C10—C11 1.393 (4) C30—O2 1.435 (3)
C10—H10 0.9500 C30—C31 1.508 (4)
C11—H11 0.9500 C30—H30A 0.9900
C12—O1 1.434 (3) C30—H30B 0.9900
C12—C13 1.510 (3) C31—C32 1.526 (4)
C12—H12A 0.9900 C31—H31A 0.9900
C12—H12B 0.9900 C31—H31B 0.9900
C13—C14 1.523 (4) C32—C33 1.519 (4)
C13—H13A 0.9900 C32—H32A 0.9900
C13—H13B 0.9900 C32—H32B 0.9900
C14—C15 1.520 (3) C33—C34 1.520 (4)
C14—H14A 0.9900 C33—H33A 0.9900
C14—H14B 0.9900 C33—H33B 0.9900
C15—C16 1.521 (4) C34—C35 1.510 (4)
C15—H15A 0.9900 C34—H34A 0.9900
C15—H15B 0.9900 C34—H34B 0.9900
C16—C17 1.510 (4) C35—C36 1.510 (4)
C16—H16A 0.9900 C35—H35A 0.9900
C16—H16B 0.9900 C35—H35B 0.9900
C17—C18 1.518 (4) C36—H36A 0.9800
C17—H17A 0.9900 C36—H36B 0.9800
C17—H17B 0.9900 C36—H36C 0.9800
C18—H18A 0.9800
N2—Ag1—N2i 180.0 N2—C19—C20 108.3 (2)
N2—Ag1—N1i 90.12 (7) C5—C19—C20 125.8 (2)
N2i—Ag1—N1i 89.88 (7) C21—C20—C19 107.8 (2)
N2—Ag1—N1 89.88 (7) C21—C20—H20 126.1
N2i—Ag1—N1 90.12 (7) C19—C20—H20 126.1
N1i—Ag1—N1 180.00 (7) C20—C21—C22 107.6 (2)
N1—C1—C23i 125.8 (2) C20—C21—H21 126.2
N1—C1—C2 108.5 (2) C22—C21—H21 126.2
C23i—C1—C2 125.8 (2) N2—C22—C23 125.9 (2)
C3—C2—C1 107.7 (2) N2—C22—C21 108.2 (2)
C3—C2—H2 126.2 C23—C22—C21 125.9 (2)
C1—C2—H2 126.2 C22—C23—C1i 126.5 (2)
C2—C3—C4 107.7 (2) C22—C23—C24 117.0 (2)
C2—C3—H3 126.1 C1i—C23—C24 116.5 (2)
C4—C3—H3 126.1 C25—C24—C29 118.0 (2)
N1—C4—C5 126.1 (2) C25—C24—C23 119.5 (2)
N1—C4—C3 107.7 (2) C29—C24—C23 122.6 (2)
C5—C4—C3 126.1 (2) C24—C25—C26 121.8 (3)
C4—C5—C19 126.2 (2) C24—C25—H25 119.1
C4—C5—C6 117.4 (2) C26—C25—H25 119.1
C19—C5—C6 116.3 (2) C27—C26—C25 119.5 (2)
C11—C6—C7 117.6 (2) C27—C26—H26 120.2
C11—C6—C5 120.3 (2) C25—C26—H26 120.2
C7—C6—C5 122.1 (2) O2—C27—C26 124.8 (2)
C6—C7—C8 121.0 (2) O2—C27—C28 115.8 (2)
C6—C7—H7 119.5 C26—C27—C28 119.4 (2)
C8—C7—H7 119.5 C27—C28—C29 120.3 (3)
C9—C8—C7 120.5 (2) C27—C28—H28 119.8
C9—C8—H8 119.7 C29—C28—H28 119.8
C7—C8—H8 119.7 C28—C29—C24 120.9 (2)
O1—C9—C8 116.3 (2) C28—C29—H29 119.5
O1—C9—C10 124.5 (2) C24—C29—H29 119.5
C8—C9—C10 119.2 (2) O2—C30—C31 108.9 (2)
C9—C10—C11 119.5 (2) O2—C30—H30A 109.9
C9—C10—H10 120.2 C31—C30—H30A 109.9
C11—C10—H10 120.2 O2—C30—H30B 109.9
C6—C11—C10 122.1 (2) C31—C30—H30B 109.9
C6—C11—H11 118.9 H30A—C30—H30B 108.3
C10—C11—H11 118.9 C30—C31—C32 113.2 (2)
O1—C12—C13 108.4 (2) C30—C31—H31A 108.9
O1—C12—H12A 110.0 C32—C31—H31A 108.9
C13—C12—H12A 110.0 C30—C31—H31B 108.9
O1—C12—H12B 110.0 C32—C31—H31B 108.9
C13—C12—H12B 110.0 H31A—C31—H31B 107.7
H12A—C12—H12B 108.4 C33—C32—C31 114.0 (2)
C12—C13—C14 112.5 (2) C33—C32—H32A 108.8
C12—C13—H13A 109.1 C31—C32—H32A 108.8
C14—C13—H13A 109.1 C33—C32—H32B 108.8
C12—C13—H13B 109.1 C31—C32—H32B 108.8
C14—C13—H13B 109.1 H32A—C32—H32B 107.7
H13A—C13—H13B 107.8 C34—C33—C32 112.8 (2)
C15—C14—C13 114.7 (2) C34—C33—H33A 109.0
C15—C14—H14A 108.6 C32—C33—H33A 109.0
C13—C14—H14A 108.6 C34—C33—H33B 109.0
C15—C14—H14B 108.6 C32—C33—H33B 109.0
C13—C14—H14B 108.6 H33A—C33—H33B 107.8
H14A—C14—H14B 107.6 C35—C34—C33 114.3 (3)
C14—C15—C16 112.6 (2) C35—C34—H34A 108.7
C14—C15—H15A 109.1 C33—C34—H34A 108.7
C16—C15—H15A 109.1 C35—C34—H34B 108.7
C14—C15—H15B 109.1 C33—C34—H34B 108.7
C16—C15—H15B 109.1 H34A—C34—H34B 107.6
H15A—C15—H15B 107.8 C34—C35—C36 113.5 (3)
C17—C16—C15 114.7 (2) C34—C35—H35A 108.9
C17—C16—H16A 108.6 C36—C35—H35A 108.9
C15—C16—H16A 108.6 C34—C35—H35B 108.9
C17—C16—H16B 108.6 C36—C35—H35B 108.9
C15—C16—H16B 108.6 H35A—C35—H35B 107.7
H16A—C16—H16B 107.6 C35—C36—H36A 109.5
C16—C17—C18 113.3 (3) C35—C36—H36B 109.5
C16—C17—H17A 108.9 H36A—C36—H36B 109.5
C18—C17—H17A 108.9 C35—C36—H36C 109.5
C16—C17—H17B 108.9 H36A—C36—H36C 109.5
C18—C17—H17B 108.9 H36B—C36—H36C 109.5
H17A—C17—H17B 107.7 C1—N1—C4 108.4 (2)
C17—C18—H18A 109.5 C1—N1—Ag1 125.72 (17)
C17—C18—H18B 109.5 C4—N1—Ag1 125.88 (16)
H18A—C18—H18B 109.5 C19—N2—C22 108.01 (19)
C17—C18—H18C 109.5 C19—N2—Ag1 126.08 (15)
H18A—C18—H18C 109.5 C22—N2—Ag1 125.83 (16)
H18B—C18—H18C 109.5 C9—O1—C12 117.12 (19)
N2—C19—C5 125.8 (2) C27—O2—C30 117.0 (2)
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Symmetry codes: (i) −x, −y, −z+2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2416).

References

  1. Bruker (2002). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
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  4. Scheidt, W. R., Mondal, J. U., Eigenbrot, C. W., Adler, A., Radonvich, L. J. & Hoard, J. L. (1986). Inorg. Chem. 25, 795–799.
  5. Sheldrick, G. M. (2004). SADABS University of Göttingen, Germany.
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  10. Zenkevich, E. I., Willert, A., Bachilo, S. M., Rempel, U., Kilin, D. S., Shulga, A. M. & von Borczyskowski, C. (2001). Mater. Sci. Eng. C, 18, 99–111.

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681103385X/bg2416sup1.cif

e-67-m1316-sup1.cif (25.4KB, cif)

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681103385X/bg2416Isup2.hkl

e-67-m1316-Isup2.hkl (271.5KB, hkl)

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

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