(Nitrato-κO,O')bis-(tryptanthrin-κN)silver(I).

In the crystal structure of the title compound, [Ag(NO(3))(C(15)H(8)N(2)O(2))(2)], tryptanthrin (indolo[2,1-b]quinazoline-6,12-dione) and silver nitrate form a 2:1 complex. The silver ion is surrounded by two tryptanthrin ligands, each coordinating through the N atoms, with Ag-N bond lengths of 2.247 (3) and 2.264 (3) Å, and an anionic nitrate ligand coordinating through two O atoms, with Ag-O bond lengths of 2.499 (3) and 2.591 (3) Å. The N-Ag-N plane and the O-Ag-O plane are roughly perpendicular, making a dihedral angle of 81.6 (2)°. In the crystal, C-H⋯O inter-actions between aromatic H atoms and keto and nitrate O atoms as well as π-π inter-actions [centroid-centroid distance = 3.706 (4) Å] give rise to a three-dimensional network.

Related literature

For the biological activity of tryptanthrin, see: Yu et al. (2007 ▶); Chan et al. (2009 ▶); Bandekar et al. (2010 ▶). For the synthesis and structural modification of tryptanthrin, see: Jao et al. (2008 ▶); Kumar et al. (2011 ▶); Chen et al. (2011 ▶). For related π–π inter­actions in natural flavonoids, see: Jiang et al. (2002 ▶, 2009 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For bond lengths and angles in a silver nitrate complex with 4,4′-trimethyl­enedipiperidine, see: Kokunov et al. (2011 ▶).

Experimental

Crystal data

[Ag(NO3)(C15H8N2O2)2]

M = 666.35

Triclinic,

a = 8.0598 (19) Å

b = 10.873 (3) Å

c = 14.541 (3) Å

α = 76.010 (4)°

β = 81.019 (4)°

γ = 84.447 (4)°

V = 1219.0 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.89 mm−1

T = 150 K

0.34 × 0.26 × 0.22 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.626, T max = 1.000

9843 measured reflections

5150 independent reflections

3893 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.108

S = 1.06

5150 reflections

388 parameters

H-atom parameters constrained

Δρmax = 1.08 e Å−3

Δρmin = −0.63 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SMART and SAINT (Bruker, 1998 ▶); data reduction: XPREP (Bruker, 1998 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: XP in SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812001821/rn2096sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812001821/rn2096Isup2.hkl

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

[Ag(NO3)(C15H8N2O2)2]	Z = 2
Mr = 666.35	F(000) = 668
Triclinic, P1	Dx = 1.815 Mg m−3
a = 8.0598 (19) Å	Mo Kα radiation, λ = 0.71074 Å
b = 10.873 (3) Å	Cell parameters from 9843 reflections
c = 14.541 (3) Å	θ = 3.2–80.9°
α = 76.010 (4)°	µ = 0.89 mm−1
β = 81.019 (4)°	T = 150 K
γ = 84.447 (4)°	Block, yellow
V = 1219.0 (5) Å3	0.34 × 0.26 × 0.22 mm

Bruker SMART 1000 CCD diffractometer	5150 independent reflections
Radiation source: fine-focus sealed tube	3893 reflections with I > 2σ(I)
graphite	Rint = 0.034
ω scans	θmax = 27.1°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −10→10
Tmin = 0.626, Tmax = 1.000	k = −13→13
9843 measured reflections	l = −18→18

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0565P)2] where P = (Fo2 + 2Fc2)/3
5150 reflections	(Δ/σ)max = 0.001
388 parameters	Δρmax = 1.08 e Å−3
0 restraints	Δρmin = −0.63 e Å−3

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
Ag1	0.16812 (4)	0.20968 (3)	0.75957 (2)	0.01945 (11)
O1	−0.1263 (4)	0.2779 (3)	1.17705 (19)	0.0228 (7)
O2	−0.0402 (3)	0.4293 (3)	0.76517 (19)	0.0203 (6)
N1	0.0735 (4)	0.2171 (3)	0.9133 (2)	0.0153 (7)
N2	−0.1018 (4)	0.3331 (3)	1.0138 (2)	0.0152 (7)
C1	−0.0672 (5)	0.2537 (4)	1.1009 (3)	0.0181 (9)
C2	0.0488 (5)	0.1456 (4)	1.0870 (3)	0.0159 (8)
C3	0.0992 (5)	0.0596 (4)	1.1675 (3)	0.0206 (9)
H3A	0.0532	0.0691	1.2298	0.025*
C4	0.2162 (5)	−0.0393 (4)	1.1561 (3)	0.0239 (10)
H4A	0.2493	−0.0986	1.2108	0.029*
C5	0.2856 (5)	−0.0522 (4)	1.0649 (3)	0.0229 (9)
H5A	0.3680	−0.1191	1.0579	0.028*
C6	0.2361 (5)	0.0311 (4)	0.9844 (3)	0.0196 (9)
H6A	0.2821	0.0206	0.9223	0.024*
C7	0.1178 (5)	0.1310 (4)	0.9955 (3)	0.0155 (8)
C8	−0.0295 (5)	0.3110 (4)	0.9265 (3)	0.0152 (8)
C9	−0.0852 (5)	0.4188 (4)	0.8498 (3)	0.0181 (9)
C10	−0.1937 (5)	0.5033 (4)	0.9006 (3)	0.0155 (8)
C11	−0.2774 (5)	0.6174 (4)	0.8666 (3)	0.0206 (9)
H11A	−0.2692	0.6537	0.7998	0.025*
C12	−0.3733 (5)	0.6781 (4)	0.9311 (3)	0.0236 (9)
H12A	−0.4334	0.7566	0.9089	0.028*
C13	−0.3827 (5)	0.6249 (4)	1.0287 (3)	0.0215 (9)
H13A	−0.4495	0.6685	1.0721	0.026*
C14	−0.2977 (5)	0.5102 (4)	1.0649 (3)	0.0198 (9)
H14A	−0.3052	0.4746	1.1317	0.024*
C15	−0.2014 (5)	0.4501 (4)	0.9990 (3)	0.0171 (8)
O1'	0.1922 (4)	0.0444 (3)	0.37176 (19)	0.0238 (7)
O2'	0.3255 (4)	−0.0370 (3)	0.76130 (19)	0.0211 (6)
N1'	0.1282 (4)	0.1466 (3)	0.6288 (2)	0.0151 (7)
N2'	0.2432 (4)	0.0131 (3)	0.5259 (2)	0.0146 (7)
C1'	0.1695 (5)	0.0793 (4)	0.4463 (3)	0.0162 (8)
C2'	0.0650 (5)	0.1903 (4)	0.4645 (3)	0.0147 (8)
C3'	−0.0166 (5)	0.2676 (4)	0.3917 (3)	0.0168 (8)
H3'A	−0.0020	0.2486	0.3304	0.020*
C4'	−0.1183 (5)	0.3713 (4)	0.4083 (3)	0.0189 (9)
H4'A	−0.1730	0.4244	0.3584	0.023*
C5'	−0.1411 (5)	0.3985 (4)	0.4989 (3)	0.0223 (9)
H5'A	−0.2129	0.4695	0.5102	0.027*
C6'	−0.0611 (5)	0.3240 (4)	0.5718 (3)	0.0202 (9)
H6'A	−0.0778	0.3431	0.6332	0.024*
C7'	0.0446 (5)	0.2203 (4)	0.5550 (3)	0.0143 (8)
C8'	0.2189 (5)	0.0498 (4)	0.6114 (3)	0.0146 (8)
C9'	0.3156 (5)	−0.0455 (4)	0.6808 (3)	0.0168 (8)
C10'	0.3883 (5)	−0.1396 (4)	0.6284 (3)	0.0172 (8)
C11'	0.4838 (5)	−0.2517 (4)	0.6561 (3)	0.0212 (9)
H11B	0.5066	−0.2801	0.7203	0.025*
C12'	0.5456 (5)	−0.3218 (4)	0.5889 (3)	0.0234 (9)
H12B	0.6109	−0.3991	0.6070	0.028*
C13'	0.5123 (5)	−0.2793 (4)	0.4945 (3)	0.0223 (9)
H13B	0.5586	−0.3270	0.4488	0.027*
C14'	0.4125 (5)	−0.1686 (4)	0.4660 (3)	0.0188 (9)
H14B	0.3877	−0.1409	0.4022	0.023*
C15'	0.3514 (5)	−0.1012 (4)	0.5342 (3)	0.0152 (8)
N3	0.4813 (4)	0.3383 (3)	0.7421 (2)	0.0211 (8)
O3	0.4698 (4)	0.2218 (3)	0.7760 (3)	0.0418 (9)
O4	0.3608 (4)	0.3988 (3)	0.7064 (2)	0.0355 (8)
O5	0.6079 (4)	0.3907 (3)	0.7475 (2)	0.0393 (8)

	U11	U22	U33	U12	U13	U23
Ag1	0.02012 (18)	0.02486 (19)	0.01477 (17)	0.00208 (12)	−0.00300 (12)	−0.00824 (13)
O1	0.0281 (16)	0.0265 (16)	0.0124 (14)	0.0007 (13)	0.0007 (12)	−0.0053 (12)
O2	0.0196 (15)	0.0273 (16)	0.0136 (14)	−0.0003 (13)	−0.0010 (12)	−0.0053 (12)
N1	0.0112 (16)	0.0187 (17)	0.0167 (17)	−0.0020 (14)	−0.0016 (13)	−0.0051 (14)
N2	0.0131 (16)	0.0203 (17)	0.0115 (16)	−0.0012 (14)	0.0017 (13)	−0.0043 (14)
C1	0.018 (2)	0.022 (2)	0.015 (2)	−0.0074 (17)	−0.0030 (17)	−0.0028 (17)
C2	0.016 (2)	0.018 (2)	0.0147 (19)	−0.0034 (16)	−0.0044 (16)	−0.0036 (16)
C3	0.020 (2)	0.025 (2)	0.016 (2)	−0.0025 (18)	−0.0014 (17)	−0.0045 (18)
C4	0.022 (2)	0.027 (2)	0.021 (2)	−0.0049 (19)	−0.0064 (18)	0.0017 (19)
C5	0.017 (2)	0.022 (2)	0.030 (2)	0.0029 (18)	−0.0062 (18)	−0.0070 (19)
C6	0.018 (2)	0.023 (2)	0.019 (2)	−0.0032 (17)	−0.0033 (17)	−0.0063 (18)
C7	0.0135 (19)	0.018 (2)	0.0160 (19)	−0.0045 (16)	−0.0042 (16)	−0.0035 (16)
C8	0.0145 (19)	0.020 (2)	0.0123 (19)	−0.0090 (17)	−0.0009 (15)	−0.0037 (16)
C9	0.0124 (19)	0.023 (2)	0.018 (2)	−0.0071 (17)	−0.0027 (16)	−0.0007 (17)
C10	0.0113 (19)	0.021 (2)	0.016 (2)	−0.0022 (16)	−0.0004 (16)	−0.0079 (17)
C11	0.016 (2)	0.027 (2)	0.019 (2)	−0.0009 (18)	−0.0040 (17)	−0.0050 (18)
C12	0.022 (2)	0.021 (2)	0.031 (2)	−0.0011 (18)	−0.0100 (19)	−0.0066 (19)
C13	0.014 (2)	0.024 (2)	0.027 (2)	−0.0031 (17)	0.0012 (17)	−0.0087 (19)
C14	0.017 (2)	0.022 (2)	0.020 (2)	−0.0067 (17)	0.0038 (17)	−0.0063 (18)
C15	0.015 (2)	0.0149 (19)	0.022 (2)	−0.0061 (16)	−0.0017 (17)	−0.0039 (17)
O1'	0.0287 (17)	0.0304 (17)	0.0143 (14)	0.0009 (13)	−0.0066 (13)	−0.0076 (13)
O2'	0.0225 (15)	0.0246 (16)	0.0161 (15)	0.0026 (12)	−0.0059 (12)	−0.0041 (12)
N1'	0.0143 (16)	0.0175 (17)	0.0127 (16)	−0.0034 (14)	−0.0008 (13)	−0.0018 (14)
N2'	0.0185 (17)	0.0136 (16)	0.0117 (16)	−0.0010 (14)	−0.0022 (14)	−0.0027 (13)
C1'	0.0128 (19)	0.020 (2)	0.017 (2)	−0.0006 (16)	−0.0020 (16)	−0.0056 (17)
C2'	0.0135 (19)	0.0169 (19)	0.0121 (18)	−0.0051 (16)	−0.0008 (15)	0.0005 (16)
C3'	0.0123 (19)	0.023 (2)	0.0137 (19)	−0.0034 (17)	−0.0002 (16)	−0.0027 (17)
C4'	0.0123 (19)	0.021 (2)	0.019 (2)	−0.0041 (17)	−0.0036 (16)	0.0054 (17)
C5'	0.016 (2)	0.016 (2)	0.031 (2)	0.0045 (17)	−0.0034 (18)	−0.0005 (18)
C6'	0.020 (2)	0.021 (2)	0.021 (2)	−0.0048 (18)	−0.0043 (17)	−0.0047 (18)
C7'	0.0108 (18)	0.0157 (19)	0.0151 (19)	−0.0038 (16)	−0.0007 (15)	−0.0010 (16)
C8'	0.0119 (19)	0.017 (2)	0.0139 (19)	−0.0077 (16)	0.0006 (15)	−0.0003 (16)
C9'	0.0132 (19)	0.018 (2)	0.017 (2)	−0.0021 (16)	0.0000 (16)	−0.0006 (17)
C10'	0.0132 (19)	0.022 (2)	0.0155 (19)	−0.0035 (17)	0.0005 (16)	−0.0037 (17)
C11'	0.016 (2)	0.021 (2)	0.025 (2)	0.0013 (17)	−0.0059 (18)	−0.0017 (18)
C12'	0.019 (2)	0.019 (2)	0.031 (2)	0.0002 (18)	−0.0050 (19)	−0.0039 (19)
C13'	0.019 (2)	0.021 (2)	0.028 (2)	−0.0047 (18)	0.0025 (18)	−0.0094 (19)
C14'	0.016 (2)	0.019 (2)	0.021 (2)	−0.0078 (17)	0.0020 (17)	−0.0041 (17)
C15'	0.0147 (19)	0.0148 (19)	0.0155 (19)	−0.0029 (16)	−0.0036 (16)	−0.0007 (16)
N3	0.0160 (18)	0.026 (2)	0.0206 (19)	0.0022 (16)	−0.0019 (15)	−0.0065 (16)
O3	0.0239 (18)	0.0247 (18)	0.071 (3)	0.0026 (14)	−0.0111 (17)	0.0015 (17)
O4	0.0246 (18)	0.0298 (18)	0.047 (2)	0.0059 (14)	−0.0132 (16)	0.0029 (16)
O5	0.0257 (18)	0.048 (2)	0.045 (2)	−0.0132 (16)	−0.0080 (16)	−0.0051 (17)

Ag1—N1'	2.247 (3)	O1'—C1'	1.215 (5)
Ag1—N1	2.264 (3)	O2'—C9'	1.212 (5)
Ag1—O3	2.499 (3)	N1'—C8'	1.277 (5)
Ag1—O4	2.591 (3)	N1'—C7'	1.398 (5)
O1—C1	1.214 (5)	N2'—C8'	1.374 (5)
O2—C9	1.209 (5)	N2'—C1'	1.393 (5)
N1—C8	1.284 (5)	N2'—C15'	1.439 (5)
N1—C7	1.400 (5)	C1'—C2'	1.457 (5)
N2—C8	1.377 (5)	C2'—C3'	1.392 (5)
N2—C1	1.401 (5)	C2'—C7'	1.413 (5)
N2—C15	1.426 (5)	C3'—C4'	1.376 (6)
C1—C2	1.463 (6)	C3'—H3'A	0.9500
C2—C3	1.398 (5)	C4'—C5'	1.400 (6)
C2—C7	1.399 (5)	C4'—H4'A	0.9500
C3—C4	1.384 (6)	C5'—C6'	1.377 (6)
C3—H3A	0.9500	C5'—H5'A	0.9500
C4—C5	1.390 (6)	C6'—C7'	1.393 (5)
C4—H4A	0.9500	C6'—H6'A	0.9500
C5—C6	1.383 (6)	C8'—C9'	1.511 (5)
C5—H5A	0.9500	C9'—C10'	1.447 (5)
C6—C7	1.397 (6)	C10'—C11'	1.386 (6)
C6—H6A	0.9500	C10'—C15'	1.402 (5)
C8—C9	1.497 (5)	C11'—C12'	1.386 (6)
C9—C10	1.458 (5)	C11'—H11B	0.9500
C10—C11	1.373 (6)	C12'—C13'	1.397 (6)
C10—C15	1.401 (5)	C12'—H12B	0.9500
C11—C12	1.373 (6)	C13'—C14'	1.394 (6)
C11—H11A	0.9500	C13'—H13B	0.9500
C12—C13	1.390 (6)	C14'—C15'	1.375 (5)
C12—H12A	0.9500	C14'—H14B	0.9500
C13—C14	1.390 (6)	N3—O4	1.231 (4)
C13—H13A	0.9500	N3—O5	1.237 (4)
C14—C15	1.385 (6)	N3—O3	1.250 (4)
C14—H14A	0.9500
N1'—Ag1—N1	147.76 (11)	C8'—N1'—C7'	116.9 (3)
N1'—Ag1—O3	114.47 (12)	C8'—N1'—Ag1	116.4 (3)
N1—Ag1—O3	94.10 (12)	C7'—N1'—Ag1	124.8 (2)
N1'—Ag1—O4	108.49 (11)	C8'—N2'—C1'	123.1 (3)
N1—Ag1—O4	101.36 (11)	C8'—N2'—C15'	109.4 (3)
O3—Ag1—O4	49.28 (10)	C1'—N2'—C15'	127.5 (3)
C8—N1—C7	116.5 (3)	O1'—C1'—N2'	121.8 (4)
C8—N1—Ag1	116.7 (3)	O1'—C1'—C2'	125.8 (4)
C7—N1—Ag1	126.7 (2)	N2'—C1'—C2'	112.4 (3)
C8—N2—C1	122.7 (3)	C3'—C2'—C7'	119.5 (4)
C8—N2—C15	109.3 (3)	C3'—C2'—C1'	119.6 (3)
C1—N2—C15	127.9 (3)	C7'—C2'—C1'	120.9 (3)
O1—C1—N2	121.7 (4)	C4'—C3'—C2'	120.2 (4)
O1—C1—C2	126.3 (4)	C4'—C3'—H3'A	119.9
N2—C1—C2	112.0 (3)	C2'—C3'—H3'A	119.9
C3—C2—C7	119.6 (4)	C3'—C4'—C5'	119.9 (4)
C3—C2—C1	118.7 (3)	C3'—C4'—H4'A	120.1
C7—C2—C1	121.6 (3)	C5'—C4'—H4'A	120.1
C4—C3—C2	119.8 (4)	C6'—C5'—C4'	121.0 (4)
C4—C3—H3A	120.1	C6'—C5'—H5'A	119.5
C2—C3—H3A	120.1	C4'—C5'—H5'A	119.5
C3—C4—C5	120.2 (4)	C5'—C6'—C7'	119.4 (4)
C3—C4—H4A	119.9	C5'—C6'—H6'A	120.3
C5—C4—H4A	119.9	C7'—C6'—H6'A	120.3
C6—C5—C4	120.9 (4)	C6'—C7'—N1'	119.0 (3)
C6—C5—H5A	119.6	C6'—C7'—C2'	120.0 (4)
C4—C5—H5A	119.6	N1'—C7'—C2'	121.0 (3)
C5—C6—C7	119.2 (4)	N1'—C8'—N2'	125.6 (4)
C5—C6—H6A	120.4	N1'—C8'—C9'	126.3 (3)
C7—C6—H6A	120.4	N2'—C8'—C9'	108.1 (3)
C6—C7—C2	120.3 (4)	O2'—C9'—C10'	131.1 (4)
C6—C7—N1	118.4 (3)	O2'—C9'—C8'	124.3 (4)
C2—C7—N1	121.2 (3)	C10'—C9'—C8'	104.6 (3)
N1—C8—N2	126.0 (4)	C11'—C10'—C15'	119.7 (4)
N1—C8—C9	125.9 (3)	C11'—C10'—C9'	131.0 (4)
N2—C8—C9	108.1 (3)	C15'—C10'—C9'	109.2 (3)
O2—C9—C10	130.4 (4)	C10'—C11'—C12'	119.0 (4)
O2—C9—C8	124.4 (4)	C10'—C11'—H11B	120.5
C10—C9—C8	105.1 (3)	C12'—C11'—H11B	120.5
C11—C10—C15	121.3 (4)	C11'—C12'—C13'	120.3 (4)
C11—C10—C9	130.6 (4)	C11'—C12'—H12B	119.9
C15—C10—C9	108.1 (3)	C13'—C12'—H12B	119.9
C12—C11—C10	118.6 (4)	C14'—C13'—C12'	121.5 (4)
C12—C11—H11A	120.7	C14'—C13'—H13B	119.2
C10—C11—H11A	120.7	C12'—C13'—H13B	119.2
C11—C12—C13	120.2 (4)	C15'—C14'—C13'	117.2 (4)
C11—C12—H12A	119.9	C15'—C14'—H14B	121.4
C13—C12—H12A	119.9	C13'—C14'—H14B	121.4
C12—C13—C14	122.2 (4)	C14'—C15'—C10'	122.3 (4)
C12—C13—H13A	118.9	C14'—C15'—N2'	129.2 (4)
C14—C13—H13A	118.9	C10'—C15'—N2'	108.5 (3)
C15—C14—C13	116.9 (4)	O4—N3—O5	121.6 (4)
C15—C14—H14A	121.5	O4—N3—O3	117.8 (3)
C13—C14—H14A	121.5	O5—N3—O3	120.6 (4)
C14—C15—C10	120.7 (4)	N3—O3—Ag1	98.2 (2)
C14—C15—N2	129.9 (4)	N3—O4—Ag1	94.3 (2)
C10—C15—N2	109.4 (3)
N1'—Ag1—N1—C8	−87.6 (3)	O4—Ag1—N1'—C7'	−64.6 (3)
O3—Ag1—N1—C8	119.3 (3)	C8'—N2'—C1'—O1'	−179.5 (4)
O4—Ag1—N1—C8	70.0 (3)	C15'—N2'—C1'—O1'	−0.3 (6)
N1'—Ag1—N1—C7	93.5 (3)	C8'—N2'—C1'—C2'	−0.1 (5)
O3—Ag1—N1—C7	−59.6 (3)	C15'—N2'—C1'—C2'	179.1 (3)
O4—Ag1—N1—C7	−108.8 (3)	O1'—C1'—C2'—C3'	−1.2 (6)
C8—N2—C1—O1	176.6 (4)	N2'—C1'—C2'—C3'	179.4 (3)
C15—N2—C1—O1	1.8 (6)	O1'—C1'—C2'—C7'	178.6 (4)
C8—N2—C1—C2	−1.6 (5)	N2'—C1'—C2'—C7'	−0.8 (5)
C15—N2—C1—C2	−176.4 (3)	C7'—C2'—C3'—C4'	−1.0 (6)
O1—C1—C2—C3	0.0 (6)	C1'—C2'—C3'—C4'	178.8 (3)
N2—C1—C2—C3	178.2 (3)	C2'—C3'—C4'—C5'	−0.6 (6)
O1—C1—C2—C7	−175.9 (4)	C3'—C4'—C5'—C6'	1.0 (6)
N2—C1—C2—C7	2.3 (5)	C4'—C5'—C6'—C7'	0.3 (6)
C7—C2—C3—C4	−0.3 (6)	C5'—C6'—C7'—N1'	178.7 (3)
C1—C2—C3—C4	−176.3 (4)	C5'—C6'—C7'—C2'	−1.9 (6)
C2—C3—C4—C5	1.0 (6)	C8'—N1'—C7'—C6'	177.5 (3)
C3—C4—C5—C6	−1.6 (6)	Ag1—N1'—C7'—C6'	−18.6 (5)
C4—C5—C6—C7	1.5 (6)	C8'—N1'—C7'—C2'	−2.0 (5)
C5—C6—C7—C2	−0.8 (6)	Ag1—N1'—C7'—C2'	162.0 (3)
C5—C6—C7—N1	177.8 (3)	C3'—C2'—C7'—C6'	2.3 (5)
C3—C2—C7—C6	0.2 (6)	C1'—C2'—C7'—C6'	−177.5 (3)
C1—C2—C7—C6	176.0 (4)	C3'—C2'—C7'—N1'	−178.3 (3)
C3—C2—C7—N1	−178.4 (3)	C1'—C2'—C7'—N1'	1.9 (5)
C1—C2—C7—N1	−2.5 (6)	C7'—N1'—C8'—N2'	1.0 (5)
C8—N1—C7—C6	−176.8 (3)	Ag1—N1'—C8'—N2'	−164.3 (3)
Ag1—N1—C7—C6	2.1 (5)	C7'—N1'—C8'—C9'	−177.9 (3)
C8—N1—C7—C2	1.8 (5)	Ag1—N1'—C8'—C9'	16.8 (5)
Ag1—N1—C7—C2	−179.3 (3)	C1'—N2'—C8'—N1'	0.0 (6)
C7—N1—C8—N2	−1.2 (5)	C15'—N2'—C8'—N1'	−179.3 (3)
Ag1—N1—C8—N2	179.9 (3)	C1'—N2'—C8'—C9'	179.1 (3)
C7—N1—C8—C9	175.6 (3)	C15'—N2'—C8'—C9'	−0.2 (4)
Ag1—N1—C8—C9	−3.3 (5)	N1'—C8'—C9'—O2'	−4.1 (6)
C1—N2—C8—N1	1.2 (6)	N2'—C8'—C9'—O2'	176.8 (4)
C15—N2—C8—N1	176.9 (4)	N1'—C8'—C9'—C10'	176.7 (4)
C1—N2—C8—C9	−176.0 (3)	N2'—C8'—C9'—C10'	−2.4 (4)
C15—N2—C8—C9	−0.4 (4)	O2'—C9'—C10'—C11'	3.8 (7)
N1—C8—C9—O2	0.9 (6)	C8'—C9'—C10'—C11'	−177.0 (4)
N2—C8—C9—O2	178.2 (4)	O2'—C9'—C10'—C15'	−174.9 (4)
N1—C8—C9—C10	−177.1 (4)	C8'—C9'—C10'—C15'	4.2 (4)
N2—C8—C9—C10	0.2 (4)	C15'—C10'—C11'—C12'	2.0 (6)
O2—C9—C10—C11	1.2 (7)	C9'—C10'—C11'—C12'	−176.6 (4)
C8—C9—C10—C11	178.9 (4)	C10'—C11'—C12'—C13'	0.3 (6)
O2—C9—C10—C15	−177.7 (4)	C11'—C12'—C13'—C14'	−2.1 (6)
C8—C9—C10—C15	0.0 (4)	C12'—C13'—C14'—C15'	1.5 (6)
C15—C10—C11—C12	−1.5 (6)	C13'—C14'—C15'—C10'	0.8 (6)
C9—C10—C11—C12	179.7 (4)	C13'—C14'—C15'—N2'	−178.2 (4)
C10—C11—C12—C13	0.8 (6)	C11'—C10'—C15'—C14'	−2.6 (6)
C11—C12—C13—C14	−0.2 (6)	C9'—C10'—C15'—C14'	176.3 (3)
C12—C13—C14—C15	0.2 (6)	C11'—C10'—C15'—N2'	176.6 (3)
C13—C14—C15—C10	−0.8 (6)	C9'—C10'—C15'—N2'	−4.5 (4)
C13—C14—C15—N2	−179.8 (4)	C8'—N2'—C15'—C14'	−177.9 (4)
C11—C10—C15—C14	1.5 (6)	C1'—N2'—C15'—C14'	2.8 (6)
C9—C10—C15—C14	−179.4 (3)	C8'—N2'—C15'—C10'	2.9 (4)
C11—C10—C15—N2	−179.3 (3)	C1'—N2'—C15'—C10'	−176.3 (3)
C9—C10—C15—N2	−0.3 (4)	O4—N3—O3—Ag1	−7.0 (4)
C8—N2—C15—C14	179.5 (4)	O5—N3—O3—Ag1	170.6 (3)
C1—N2—C15—C14	−5.2 (6)	N1'—Ag1—O3—N3	97.8 (3)
C8—N2—C15—C10	0.4 (4)	N1—Ag1—O3—N3	−97.6 (3)
C1—N2—C15—C10	175.8 (4)	O4—Ag1—O3—N3	3.9 (2)
N1—Ag1—N1'—C8'	−103.8 (3)	O5—N3—O4—Ag1	−170.9 (3)
O3—Ag1—N1'—C8'	46.6 (3)	O3—N3—O4—Ag1	6.7 (4)
O4—Ag1—N1'—C8'	99.4 (3)	N1'—Ag1—O4—N3	−110.7 (2)
N1—Ag1—N1'—C7'	92.3 (3)	N1—Ag1—O4—N3	81.7 (3)
O3—Ag1—N1'—C7'	−117.4 (3)	O3—Ag1—O4—N3	−3.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C3'—H3'A···O1i	0.95	2.52	3.348 (4)	145
C4'—H4'A···O4ii	0.95	2.42	3.300 (3)	153
C3—H3A···O1'iii	0.95	2.45	3.139 (4)	130
C6'—H6'A···O2	0.95	2.40	3.313 (4)	161
C4—H4A···O3iv	0.95	2.53	3.190 (2)	127
C6—H6A···O2'	0.95	2.53	3.454 (3)	164
C13'—H13B···O4v	0.95	2.53	3.453 (2)	163
C14—H14A···O1	0.95	2.47	2.996 (5)	115
C14'—H14B···O1'	0.95	2.43	2.970 (3)	116

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3′—H3′A⋯O1i	0.95	2.52	3.348 (4)	145
C4′—H4′A⋯O4ii	0.95	2.42	3.300 (3)	153
C3—H3A⋯O1′iii	0.95	2.45	3.139 (4)	130
C6′—H6′A⋯O2	0.95	2.40	3.313 (4)	161
C4—H4A⋯O3iv	0.95	2.53	3.190 (2)	127
C6—H6A⋯O2′	0.95	2.53	3.454 (3)	164
C13′—H13B⋯O4v	0.95	2.53	3.453 (2)	163
C14—H14A⋯O1	0.95	2.47	2.996 (5)	115
C14′—H14B⋯O1′	0.95	2.43	2.970 (3)	116

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .