(Nitrato-κ2O,O′)bis­(tryptanthrin-κN)silver(I)

Wu, J.; Huang, C.; Li, G.-Q.; Tian, H.-Y.; Jiang, R.-W.

doi:10.1107/S1600536812001821

(Nitrato-κ²O,O′)bis(tryptanthrin-κN)silver(I)

J. Wu, C. Huang, G.-Q. Li, H.-Y. Tian and R.-W. Jiang

In the crystal structure of the title compound, [Ag(NO₃)(C₁₅H₈N₂O₂)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 interactions between aromatic H atoms and keto and nitrate O atoms as well as π–π interactions [centroid-centroid distance = 3.706 (4) Å] give rise to a three-dimensional network.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536812001821/rn2096sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536812001821/rn2096Isup2.hkl Contains datablock I

CCDC reference: 867992

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.006 Å
R factor = 0.043
wR factor = 0.108
Data-to-parameter ratio = 13.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT934_ALERT_3_B Number of (Iobs-Icalc)/SigmaW .gt. 10 Outliers .          3

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......      0.960
PLAT125_ALERT_4_C No '_symmetry_space_group_name_Hall' Given .....          ?
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N3
PLAT737_ALERT_1_C D...A   Calc    3.190(6), Rep    3.190(2) ......        3.0 su-Ra
              C4   -O3      1.555   2.657                    #         67
PLAT737_ALERT_1_C D...A   Calc    3.452(5), Rep    3.453(2) ......        2.5 su-Ra
              C13' -O4      1.555   2.656                    #         67
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600        121
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600         96
PLAT975_ALERT_2_C Positive Residual Density at 0.93A from N1'    .       0.44 eA-3

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal ..........    0.00400 Deg.
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          4
PLAT982_ALERT_1_G The  C-f'=     0.018 Deviates from the  IT-value      0.003
PLAT982_ALERT_1_G The Ag-f'=     0.131 Deviates from the  IT-value     -0.897
PLAT982_ALERT_1_G The  N-f'=     0.031 Deviates from the  IT-value      0.006
PLAT982_ALERT_1_G The  O-f'=     0.049 Deviates from the  IT-value      0.011
PLAT983_ALERT_1_G The  C-f"=     0.009 Deviates from the  IT-Value      0.002
PLAT983_ALERT_1_G The Ag-f"=     4.282 Deviates from the  IT-Value      1.102
PLAT983_ALERT_1_G The  N-f"=     0.018 Deviates from the  IT-Value      0.003
PLAT983_ALERT_1_G The  O-f"=     0.032 Deviates from the  IT-Value      0.006

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
   9 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  11 ALERT level G = General information/check it is not something unexpected

  11 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

Tryptanthrin is an indole quinazoline alkaloid isolated from Folium Isatidis (Chen et al., 2011). It was found to inhibit the murine myelomonocytic leukemia cells by causing cell cycle arrest and triggering cell differentiation (Chan et al., 2009), and reverse the doxorubicin resistance in breast cancer cells by inhibition of MDR1 (Yu et al., 2007). It was also found to inhibit the growth of Escherichia coli through intercalation into DNA (Bandekar et al., 2010). In addition, synthesis of tryptanthrin (Kumar et al., 2011) and its derivatives (Chen et al., 2011) were reported.

Tryptanthrin and silver nitrate form a 2:1 complex. The same proportions were used in the synthesis. Both the two tryptanthrin molecules are essentially planar with mean deviations of 0.0066 (4) Å and 0.0054 (3) Å, respectively, and make a dihedral angle of 2.9 (2)°. The nitrate group makes dihedral angles of 89.5 (3)° and 105.1 (4)° with the two tryptanthrin molecules. The silver ion is coordinated with two oxygen atoms from the anionic nitrate ligand with bond distances of 2.499 (3) Å and 2.591 (3) Å, and two nitrogen atoms from the tryptanthrin ligands with bond distances of 2.266 (3) Å and 2.249 (3) Å, which are slightly longer than those reported in silver nitrate complex with 4,4'-trimethylenedipiperidine [2.192 (5) Å and 2.212 (5) Å] (Kokunov et al., 2011). The N—Ag—N plane and the O—Ag—O plane are roughly perpendicular with a dihedral angle of 81.6 (2)°. The bond distances and bond angles in both tryptanthrin molecules are all normal (Allen et al., 1987).

Short intermolecular C—H···O interactions (Table 1) between the tryptanthrin methane H atoms and the nitrate ligand [C4'—H···O4, 3.300 (3) Å, C13'—H···O4, 3.453 (2) Å] linked adjacent molecules into layers. Adjacent layers were linked by π-π interactions between the benzene rings [centroid-centroid distance 3.706 (4) Å and displacement angle 4.5 (2)°]. The centroid-centroid distance observed in title compound is similar to those in natural flavonoids (Jiang, et al., 2002 and 2009).

Related literature top

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 top

Tryptanthrin (12.4 mg, 0.05 mmol) was dissolved in a solution including methanol (1 ml) and chloroform (3 ml). silver nitrate (17.0 mg, 0.1 mmol) was dissolved in methanol (1 ml) and was added into the tryptanthrin solution. Three days later, the crystals were obtained via slow evaporation at room temperature.

Computing details top

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 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound showing 30% probability displacement ellipsoids.
	Fig. 2. The packing diagram viewed down the c axis. The dashed lines represent intermolecular C—H···O interactions.

Bis(indolo[2,1-b]quinazoline-6,12-dione-κN)(nitrato- κ²O,O')silver(I) top

Crystal data top

[Ag(NO₃)(C₁₅H₈N₂O₂)₂]	Z = 2
M_r = 666.35	F(000) = 668
Triclinic, P1	D_x = 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

Data collection top

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

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0565P)²] where P = (F_o² + 2F_c²)/3
5150 reflections	(Δ/σ)_max = 0.001
388 parameters	Δρ_max = 1.08 e Å⁻³
0 restraints	Δρ_min = −0.63 e Å⁻³

Crystal data top

[Ag(NO₃)(C₁₅H₈N₂O₂)₂]	γ = 84.447 (4)°
M_r = 666.35	V = 1219.0 (5) Å³
Triclinic, P1	Z = 2
a = 8.0598 (19) Å	Mo Kα radiation
b = 10.873 (3) Å	µ = 0.89 mm⁻¹
c = 14.541 (3) Å	T = 150 K
α = 76.010 (4)°	0.34 × 0.26 × 0.22 mm
β = 81.019 (4)°

Data collection top

Bruker SMART 1000 CCD diffractometer	5150 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	3893 reflections with I > 2σ(I)
T_min = 0.626, T_max = 1.000	R_int = 0.034
9843 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.06	Δρ_max = 1.08 e Å⁻³
5150 reflections	Δρ_min = −0.63 e Å⁻³
388 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	0.16812 (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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O3^iv	0.95	2.53	3.190 (2)	127
C6—H6A···O2′	0.95	2.53	3.454 (3)	164
C13′—H13B···O4^v	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) x, y, z−1; (ii) −x, −y+1, −z+1; (iii) x, y, z+1; (iv) −x+1, −y, −z+2; (v) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	[Ag(NO₃)(C₁₅H₈N₂O₂)₂]
M_r	666.35
Crystal system, space group	Triclinic, P1
Temperature (K)	150
a, b, c (Å)	8.0598 (19), 10.873 (3), 14.541 (3)
α, β, γ (°)	76.010 (4), 81.019 (4), 84.447 (4)
V (Å³)	1219.0 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.89
Crystal size (mm)	0.34 × 0.26 × 0.22

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.626, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	9843, 5150, 3893
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.641

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.108, 1.06
No. of reflections	5150
No. of parameters	388
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.08, −0.63

Computer programs: SMART (Bruker, 1998), SMART and SAINT (Bruker, 1998), XPREP (Bruker, 1998), XP in SHELXTL (Sheldrick, 2008).