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

Liao, J.-X.; Zhao, H.-B.; Yang, D.-L.; Chen, L.; Wang, B.-Y.

doi:10.1107/S160053681103385X

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page m1316

doi:10.1107/S160053681103385X

Open

access

{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 and Bang-Ying Wang ^c

^aEnvironmental Engineering, Dongguan University of Technology, Guangdong, 523808, People's Republic of China, ^bCleaner Production Center, Dongguan University of Technology, Guangdong, 523808, People's Republic of China, and ^cDepartment of Organic Chemistry, the College of Chemistry, Xiangtan University, Hunan, 411105, People's Republic of China
^*Correspondence e-mail: zhhbhanlf@163.com

(Received 25 July 2011; accepted 19 August 2011; online 27 August 2011)

The title compound, [Ag(C₇₂H₈₄N₄O₄)], crystallizes with the Ag^II 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 Ag^II 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 ).

Experimental

Crystal data

[Ag(C₇₂H₈₄N₄O₄)]
M_r = 1177.30
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.036
wR(F²) = 0.091
S = 1.02
5544 reflections
369 parameters
H-atom parameters constrained
Δρ_max = 0.53 e Å⁻³
Δρ_min = −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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681103385X/bg2416sup1.cif

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

checkCIF report

Comment top

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 Ag^II 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 Ag^II 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.

Related literature top

For background information [on metalloporphyrins and their derivatives?] see Fu et al. (2009); Jurow et al. (2010); Taniguchi et al. (2010); Zenkevich et al. (2001). For related structures, see: Scheidt et al. (1986); Xu et al. (2007).

Experimental top

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.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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 (Sheldrick, 2008).

Figures top

Fig. 1. A view of (I), with the atom-labeling scheme and 50% probability displacement ellipsoids. Symmetry codes: (i) -x, -y, -z+2.

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

Crystal data top

[Ag(C₇₂H₈₄N₄O₄)]	F(000) = 1246
M_r = 1177.30	D_x = 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

Data collection top

Bruker APEX CCD diffractometer	5544 independent reflections
Radiation source: fine-focus sealed tube	4385 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −17→18
T_min = 0.916, T_max = 0.964	k = −22→19
18310 measured reflections	l = −12→12

Refinement top

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(F_o²) + (0.0483P)² + 0.7718P] where P = (F_o² + 2F_c²)/3
5544 reflections	(Δ/σ)_max < 0.001
369 parameters	Δρ_max = 0.53 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

[Ag(C₇₂H₈₄N₄O₄)]	V = 3140.0 (4) Å³
M_r = 1177.30	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.850 (1) Å	µ = 0.37 mm⁻¹
b = 19.1896 (12) Å	T = 185 K
c = 10.3285 (7) Å	0.24 × 0.17 × 0.10 mm
β = 91.724 (1)°

Data collection top

Bruker APEX CCD diffractometer	5544 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	4385 reflections with I > 2σ(I)
T_min = 0.916, T_max = 0.964	R_int = 0.035
18310 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.091	H-atom parameters constrained
S = 1.02	Δρ_max = 0.53 e Å⁻³
5544 reflections	Δρ_min = −0.20 e Å⁻³
369 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x, −y, −z+2.

Experimental details

Crystal data
Chemical formula	[Ag(C₇₂H₈₄N₄O₄)]
M_r	1177.30
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	185
a, b, c (Å)	15.850 (1), 19.1896 (12), 10.3285 (7)
β (°)	91.724 (1)
V (Å³)	3140.0 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.37
Crystal size (mm)	0.24 × 0.17 × 0.10

Data collection
Diffractometer	Bruker APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.916, 0.964
No. of measured, independent and observed [I > 2σ(I)] reflections	18310, 5544, 4385
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.091, 1.02
No. of reflections	5544
No. of parameters	369
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.20

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

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

References

Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fu, B., Yu, H.-C, Huang, J.-W., Zhao, P., Liu, J. & Ji, L.-N. (2009). J. Mol. Catal. A Chem. 298, 74–80. CrossRef CAS Google Scholar
Jurow, M., Schuckman, A. E., Batteas, J. D. & Drain, C. M. (2010). Coord. Chem. Rev. 254, 2297–2310. CrossRef CAS Google Scholar
Scheidt, W. R., Mondal, J. U., Eigenbrot, C. W., Adler, A., Radonvich, L. J. & Hoard, J. L. (1986). Inorg. Chem. 25, 795–799. CSD CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany. 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
Taniguchi, M. & Lindsey, J. S. (2010). Tetrahedron, 66, 5549–5565. CrossRef CAS Google Scholar
Xu, Y.-J., Yang, X.-X., Cao, H. & Zhao, H.-B. (2007). Acta Cryst. E63, m1437. Web of Science CSD CrossRef IUCr Journals Google Scholar
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. CrossRef Google Scholar