Crystal structure of a twisted-ribbon type double-stranded AgI coordination polymer: catena-poly[[silver(I)-μ3-bis­(pyridin-3-ylmeth­yl)sulfane-κ3N:N′:S] nitrate]

Moon, S.-H.; Kang, Y.; Park, K.-M.

doi:10.1107/S2056989017013925

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ISSN: 2056-9890

Volume 73| Part 10| October 2017| Pages 1587-1589

https://doi.org/10.1107/S2056989017013925

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Crystal structure of a twisted-ribbon type double-stranded Ag^I coordination polymer: catena-poly[[silver(I)-μ₃-bis(pyridin-3-ylmethyl)sulfane-κ³N:N′:S] nitrate]

Suk-Hee Moon,^a Youngjin Kang ^b ^* and Ki-Min Park ^c ^*

^aDepartment of Food and Nutrition, Kyungnam College of Information and Technology, Busan 47011, Republic of Korea, ^bDivision of Science Education, Kangwon National University, Chuncheon 24341, Republic of Korea, and ^cResearch institute of Natural Science, Gyeongsang National University, Jinju 52828, Republic of Korea
^*Correspondence e-mail: kangy@kangwon.ac.kr, kmpark@gnu.ac.kr

Edited by J. Simpson, University of Otago, New Zealand (Received 24 September 2017; accepted 27 September 2017; online 29 September 2017)

The asymmetric unit in the title compound, {[Ag(C₁₂H₁₂N₂S)]·NO₃}_n or {[AgL]·NO₃}_n, L = bis(pyridin-3-ylmethyl)sulfane, consists of an Ag^I cation bound to a pyridine N atom of an L ligand and an NO₃⁻ anion that is disordered over two orientations in an 0.570 (17):0.430 (17) occupancy ratio. Each Ag^I cation is coordinated by two pyridine N atoms from adjacent L ligands to form an infinite zigzag chain along [110]. In addition, each Ag^I ion binds to an S donor from a third L ligand in an adjacent parallel chain, resulting in the formation of a twisted-ribbon type of double-stranded chain propagating along the [110] or [1-10] directions. The Ag^I atom is displaced out of the trigonal N₂S coordination plane by 0.371 (3) Å because of interactions between the Ag^I cation and O atoms of the disordered nitrate anions. Intermolecular π–π stacking interactions [centroid-to-centroid distance = 3.824 (3) Å] occur between one pair of corresponding pyridine rings in the double-stranded chain. In the crystal, the double-stranded chains are alternately stacked along the c axis with alternate stacks linked by intermolecular π–π stacking interactions [centroid-to-centroid distance = 3.849 (3) Å], generating a three-dimensional supramolecular architecture. Weak intermolecular C—H⋯O hydrogen bonds between the polymer chains and the O atoms of the nitrate anions also occur.

Keywords: crystal structure; silver(I); tridentate ligand; double-stranded chain; hydrogen bonding; π–π interactions.

CCDC reference: 1576726

1. Chemical context

Among the diverse key factors in the development of Ag^I coordination polymers, the structures of the spacer ligands play important roles in determining the structural topology of the self-assembled polymer units (Zheng et al., 2009 ; Liu et al., 2011 ). For this reason, continuous efforts have focused on the design and development of such suitable ligands. In particular, dipyridyl-type molecules functioning as bridging ligands have been widely used to construct diverse Ag^I coordination polymers with fascinating structures and attractive functional properties (Leong & Vittal, 2011 ; Moulton & Zaworotko, 2001 ; Wang et al., 2012 ). We have also reported several Ag^I coordination polymers with interesting structures using dipyridyl-type ligands (Lee et al., 2012 , 2015 ; Moon et al., 2015 , 2016 ; Park et al., 2010 ). The continuing interest in dipyridyl-type-ligand-based Ag^I coordination polymers prompted us to investigate the use of the ligand bis(pyridin-3-ylmethyl)sulfane (L), which can coordinate to three Ag^I cations in a T-shape via the two pyridine nitrogen donors as a bridgehead and the sulfur donor atoms, binding to the Ag^I cations at both ends of the dipyridyl bridge as well as at its centre. A reaction of silver(I) nitrate with L (synthesized using a literature procedure; Park et al., 2010; Lee et al., 2012) afforded the title compound. Herein, we report its one-dimensional twisted-ribbon type double-stranded chain structure in the crystal.

2. Structural commentary

As shown in Fig. 1, the asymmetric unit of the title compound comprises one Ag^I cation, bound to the N1 pyridine atom of a bis(pyridin-3-ylmethyl)sulfane ligand, L, and an NO₃⁻ anion that is disordered over two orientations in an 0.570 (17):0.430 (17) occupancy ratio. Pyridine N atoms N1 and N2 from two symmetry-related L ligands bind to the Ag^I cations to form an infinite zigzag chain. In addition, each Ag^I ion binds to an S1 donor from a third L ligand in an adjacent parallel chain, resulting in the formation of a twisted-ribbon type of double-stranded chain propagating along the [110] or [1 $[\overline{1}]$ 0] directions (Figs. 2 and 3). The Ag^I atom is therefore three-coordinated and the coordination geometry around the Ag^I cation can be considered as a highly distorted trigonal plane. Selected bond lengths and angles around the Ag1 atom are given in Table 1. N—Ag—N and N—Ag—S angles fall in the range 106.03 (12)–133.18 (12)°, deviating significantly from ideal trigonal–planar geometry. This may reflect the influence of additional Ag⋯O–NO₂⁻ interactions between the Ag^I ion and O atoms of the disordered nitrate anion [Ag1⋯O1 = 2.730 (18), Ag1⋯O1′ = 2.55 (2) Å; indicated by a dashed line in Fig. 1]. The Ag^I atom is displaced out of the trigonal N1, S1, N2 coordination plane by 0.372 (2) Å. The two pyridine rings coordinated to the Ag^I centre are tilted by 53.20 (15)° with respect to each other. In the double-stranded chain, intermolecular π–π stacking interactions between the N1-pyridine rings [Cg1⋯Cg1ⁱ = 3.824 (3) Å; yellow dashed lines in Fig. 2; Cg1 is the centroid of the N1/C1–C5 ring; symmetry code: (i) −x + $[{1\over 2}]$ , −y + $[{1\over 2}]$ , −z + 1] contribute to the stabilization of the double-stranded chain.

Table 1
Selected geometric parameters (Å, °)

Ag1—N2ⁱ	2.276 (5)	Ag1—S1ⁱⁱ	2.5305 (14)
Ag1—N1	2.333 (4)

N2ⁱ—Ag1—N1	113.22 (16)	N1—Ag1—S1ⁱⁱ	106.03 (12)
N2ⁱ—Ag1—S1ⁱⁱ	133.18 (12)
Symmetry codes: (i) $[x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Figure 1
View of the molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Disordered O atoms of the NO₃⁻ anion have been omitted for clarity. The dashed line represents the Ag⋯O interaction. [Symmetry codes: (i) x − $[{1\over 2}]$ , y + $[{1\over 2}]$ , z; (ii) −x + $[{1\over 2}]$ , −y + $[{1\over 2}]$ , −z + 1; (iii) x + $[{1\over 2}]$ , y − $[{1\over 2}]$ , z.]

Figure 2
The double-stranded polymeric chains propagating along the [110] (upper chain) and [1 $[\overline{1}]$ 0] (lower chain) directions. Yellow dashed lines represent intermolecular π–π stacking interactions [centroid-to-centroid distance = 3.824 (3) Å] between the N1-containing pyridine rings in the chain. NO₃⁻ anions and H atoms have been omitted for clarity.

Figure 3
Three-dimensional supramolecular network via intermolecular π–π stacking interactions (yellow dashed lines) between the N2-containing pyridine rings. NO₃⁻ anions and H atoms have been omitted for clarity.

3. Supramolecular features

As shown in Fig. 3, the double-stranded chains propagate along the [110] and [1 $[\overline{1}]$ 0] directions in the crystal and are alternately stacked along the c axis. Adjacent chains are linked by intermolecular π–π stacking interactions between N2-pyridine rings [Cg2⋯Cg2ⁱⁱ = 3.849 (3) Å; yellow dashed lines in Fig. 3; Cg2 is the centroid of the N2/C8–C12 ring; symmetry code: (ii) −x + 1, y, −z + $[{1\over 2}]$ ], resulting in the formation of a three-dimensional supramolecular architecture (Fig. 3). Weak intermolecular C—H⋯O hydrogen bonds (Table 2) between the double-stranded chains and the NO₃⁻ anions are also observed in the crystal.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O2	0.93	2.59	2.924 (12)	102
C5—H5⋯O2ⁱⁱⁱ	0.93	2.60	3.318 (14)	135
C6—H6A⋯O2^iv	0.97	2.52	3.464 (14)	163
C6—H6B⋯O2′^v	0.97	2.60	3.44 (2)	145
C7—H7B⋯O3′^iv	0.97	2.38	3.233 (15)	147
C9—H9⋯O1^vi	0.93	2.49	3.221 (18)	136
C12—H12⋯O3^vii	0.93	2.45	3.256 (12)	145
Symmetry codes: (iii) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (iv) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) x, y-1, z; (vi) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (vii) $[-x+{\script{1\over 2}}, y-{\script{3\over 2}}, -z+{\script{1\over 2}}]$ .

4. Synthesis and crystallization

The L ligand was synthesized according to a literature method (Park et al., 2010; Lee et al., 2012). Colourless plate-like X-ray quality single crystals of the title compound were obtained by vapor diffusion of diethyl ether into a DMSO solution of the L ligand with AgNO₃ in a 1:1 molar ratio.

5. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. The NO₃⁻ anion is disordered over two orientations and the occupancies of the disorder components refined to a 0.570 (17):0.430 (17) ratio. The anisotropic displacement ellipsoids of four oxygen atoms (O3, O1′, O2′ and O3′) in the disordered NO₃⁻ anion were very elongated and therefore ISOR restraints were applied for these atoms (McArdle, 1995 ; Sheldrick, 2008 ). All H atoms were positioned geometrically and refined as riding: C—H = 0.93 Å for Csp²—H and 0.97 Å for methylene C—H, with U_iso(H) = 1.2U_eq(C).

Table 3
Experimental details

Crystal data
Chemical formula	[Ag(C₁₂H₁₂N₂S)]NO₃
M_r	386.18
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	22.432 (3), 8.1656 (12), 15.036 (2)
β (°)	98.636 (3)
V (Å³)	2722.9 (7)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	1.64
Crystal size (mm)	0.25 × 0.20 × 0.05

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2014 )
T_min, T_max	0.658, 0.896
No. of measured, independent and observed [I > 2σ(I)] reflections	7550, 2676, 1763
R_int	0.079
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.109, 0.97
No. of reflections	2676
No. of parameters	209
No. of restraints	24
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.66, −0.66
Computer programs: APEX2 and SAINT (Bruker, 2014), SHELXS97 and SHELXTL (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015 ), DIAMOND (Brandenburg, 2010 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1576726

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S2056989017013925/sj5535sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989017013925/sj5535Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

catena-Poly[[silver(I)-µ₃-bis(pyridin-3-ylmethyl)sulfane-κ³N:N':S] nitrate] top

Crystal data top

[Ag(C₁₂H₁₂N₂S)]NO₃	F(000) = 1536
M_r = 386.18	D_x = 1.884 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 22.432 (3) Å	Cell parameters from 3272 reflections
b = 8.1656 (12) Å	θ = 1.8–28.3°
c = 15.036 (2) Å	µ = 1.64 mm⁻¹
β = 98.636 (3)°	T = 298 K
V = 2722.9 (7) Å³	Plate, colourless
Z = 8	0.25 × 0.20 × 0.05 mm

Data collection top

Bruker APEXII CCD diffractometer	1763 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.079
Absorption correction: multi-scan (SADABS; Bruker, 2014)	θ_max = 26.0°, θ_min = 2.7°
T_min = 0.658, T_max = 0.896	h = −27→26
7550 measured reflections	k = −10→8
2676 independent reflections	l = −18→9

Refinement top

Refinement on F²	24 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.109	w = 1/[σ²(F_o²) + (0.0526P)²] where P = (F_o² + 2F_c²)/3
S = 0.97	(Δ/σ)_max < 0.001
2676 reflections	Δρ_max = 0.66 e Å⁻³
209 parameters	Δρ_min = −0.66 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Ag1	0.13008 (2)	0.47824 (6)	0.49130 (3)	0.05552 (19)
S1	0.33342 (6)	−0.07112 (16)	0.34926 (9)	0.0417 (3)
N1	0.2163 (2)	0.4068 (5)	0.4306 (3)	0.0460 (11)
N2	0.5458 (2)	−0.1552 (6)	0.4256 (3)	0.0501 (11)
N3	0.1183 (3)	0.8084 (7)	0.3663 (4)	0.0662 (15)
O1	0.0800 (7)	0.756 (2)	0.4114 (15)	0.106 (6)	0.570 (17)
O2	0.1701 (6)	0.7472 (18)	0.3893 (9)	0.117 (5)	0.570 (17)
O3	0.1169 (6)	0.9256 (15)	0.3181 (8)	0.105 (5)	0.570 (17)
O1'	0.1009 (9)	0.764 (3)	0.4311 (15)	0.072 (5)	0.430 (17)
O2'	0.1641 (12)	0.845 (3)	0.3590 (16)	0.133 (8)	0.430 (17)
O3'	0.0762 (7)	0.815 (2)	0.2930 (9)	0.096 (6)	0.430 (17)
C1	0.2231 (2)	0.2722 (6)	0.3824 (3)	0.0391 (12)
H1	0.1905	0.2011	0.3699	0.047*
C2	0.2760 (2)	0.2324 (6)	0.3498 (3)	0.0386 (12)
C3	0.3244 (2)	0.3392 (6)	0.3697 (4)	0.0464 (13)
H3	0.3606	0.3175	0.3487	0.056*
C4	0.3188 (2)	0.4778 (6)	0.4206 (4)	0.0483 (13)
H4	0.3510	0.5498	0.4349	0.058*
C5	0.2640 (3)	0.5066 (6)	0.4498 (4)	0.0503 (13)
H5	0.2601	0.5995	0.4842	0.060*
C6	0.2786 (2)	0.0785 (7)	0.2966 (4)	0.0466 (13)
H6A	0.2884	0.1065	0.2378	0.056*
H6B	0.2389	0.0284	0.2877	0.056*
C7	0.3975 (2)	−0.0395 (7)	0.2890 (4)	0.0478 (13)
H7A	0.3870	−0.0722	0.2266	0.057*
H7B	0.4089	0.0752	0.2908	0.057*
C8	0.4488 (2)	−0.1419 (6)	0.3345 (3)	0.0426 (12)
C9	0.4985 (2)	−0.0697 (7)	0.3829 (4)	0.0451 (12)
H9	0.4997	0.0440	0.3866	0.054*
C10	0.5422 (3)	−0.3178 (8)	0.4195 (4)	0.0591 (16)
H10	0.5739	−0.3792	0.4496	0.071*
C11	0.4946 (3)	−0.4000 (7)	0.3715 (5)	0.0631 (17)
H11	0.4944	−0.5137	0.3684	0.076*
C12	0.4474 (3)	−0.3106 (7)	0.3282 (4)	0.0538 (15)
H12	0.4147	−0.3631	0.2947	0.065*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.0456 (3)	0.0747 (3)	0.0449 (3)	0.0096 (2)	0.00258 (18)	−0.0054 (2)
S1	0.0366 (6)	0.0477 (7)	0.0410 (7)	0.0028 (5)	0.0063 (5)	−0.0036 (6)
N1	0.046 (3)	0.051 (3)	0.042 (3)	0.003 (2)	0.010 (2)	−0.001 (2)
N2	0.043 (3)	0.062 (3)	0.045 (3)	0.007 (2)	0.006 (2)	−0.008 (2)
N3	0.076 (4)	0.060 (4)	0.066 (4)	0.007 (3)	0.020 (4)	−0.003 (3)
O1	0.071 (9)	0.100 (9)	0.147 (15)	−0.021 (7)	0.014 (9)	0.046 (9)
O2	0.102 (8)	0.110 (9)	0.127 (10)	0.063 (7)	−0.016 (7)	0.004 (8)
O3	0.132 (8)	0.088 (7)	0.102 (7)	0.033 (6)	0.045 (6)	0.049 (6)
O1'	0.081 (7)	0.069 (6)	0.068 (6)	−0.005 (5)	0.013 (5)	0.003 (4)
O2'	0.125 (11)	0.145 (11)	0.131 (11)	−0.033 (9)	0.027 (8)	−0.006 (8)
O3'	0.100 (9)	0.110 (9)	0.074 (8)	0.040 (7)	−0.001 (6)	−0.019 (6)
C1	0.037 (3)	0.045 (3)	0.033 (3)	0.003 (2)	0.000 (2)	0.003 (2)
C2	0.041 (3)	0.041 (3)	0.033 (3)	0.006 (2)	0.002 (2)	0.007 (2)
C3	0.042 (3)	0.050 (3)	0.048 (3)	0.001 (2)	0.010 (2)	0.006 (3)
C4	0.046 (3)	0.043 (3)	0.054 (3)	−0.006 (2)	0.003 (3)	0.008 (3)
C5	0.059 (3)	0.047 (3)	0.043 (3)	0.003 (3)	0.004 (3)	−0.004 (3)
C6	0.045 (3)	0.056 (3)	0.037 (3)	0.006 (2)	0.002 (2)	0.000 (3)
C7	0.039 (3)	0.064 (3)	0.040 (3)	0.002 (2)	0.006 (2)	−0.003 (3)
C8	0.037 (3)	0.055 (3)	0.039 (3)	0.001 (2)	0.015 (2)	−0.004 (3)
C9	0.042 (3)	0.051 (3)	0.043 (3)	0.006 (2)	0.009 (2)	−0.005 (3)
C10	0.051 (4)	0.064 (4)	0.063 (4)	0.019 (3)	0.010 (3)	0.005 (3)
C11	0.060 (4)	0.048 (3)	0.085 (5)	0.003 (3)	0.023 (4)	−0.002 (3)
C12	0.045 (3)	0.061 (4)	0.059 (4)	−0.004 (3)	0.018 (3)	−0.012 (3)

Geometric parameters (Å, º) top

Ag1—N2ⁱ	2.276 (5)	C2—C3	1.389 (7)
Ag1—N1	2.333 (4)	C2—C6	1.495 (7)
Ag1—S1ⁱⁱ	2.5305 (14)	C3—C4	1.383 (7)
Ag1—O1'	2.55 (2)	C3—H3	0.9300
S1—C6	1.828 (5)	C4—C5	1.385 (8)
S1—C7	1.829 (5)	C4—H4	0.9300
S1—Ag1ⁱⁱ	2.5305 (14)	C5—H5	0.9300
N1—C1	1.338 (6)	C6—H6A	0.9700
N1—C5	1.342 (7)	C6—H6B	0.9700
N2—C10	1.333 (7)	C7—C8	1.500 (7)
N2—C9	1.348 (7)	C7—H7A	0.9700
N2—Ag1ⁱⁱⁱ	2.276 (5)	C7—H7B	0.9700
N3—O2'	1.09 (2)	C8—C9	1.371 (7)
N3—O1'	1.16 (2)	C8—C12	1.381 (7)
N3—O3	1.199 (11)	C9—H9	0.9300
N3—O1	1.246 (17)	C10—C11	1.371 (9)
N3—O2	1.265 (12)	C10—H10	0.9300
N3—O3'	1.340 (14)	C11—C12	1.367 (8)
C1—C2	1.389 (7)	C11—H11	0.9300
C1—H1	0.9300	C12—H12	0.9300

N2ⁱ—Ag1—N1	113.22 (16)	C3—C4—H4	120.9
N2ⁱ—Ag1—S1ⁱⁱ	133.18 (12)	C5—C4—H4	120.9
N1—Ag1—S1ⁱⁱ	106.03 (12)	N1—C5—C4	123.1 (5)
N2ⁱ—Ag1—O1'	97.5 (4)	N1—C5—H5	118.4
N1—Ag1—O1'	105.9 (5)	C4—C5—H5	118.4
S1ⁱⁱ—Ag1—O1'	95.2 (5)	C2—C6—S1	114.0 (4)
C6—S1—C7	102.7 (3)	C2—C6—H6A	108.7
C6—S1—Ag1ⁱⁱ	108.12 (18)	S1—C6—H6A	108.7
C7—S1—Ag1ⁱⁱ	105.08 (18)	C2—C6—H6B	108.7
C1—N1—C5	117.6 (5)	S1—C6—H6B	108.7
C1—N1—Ag1	125.9 (3)	H6A—C6—H6B	107.6
C5—N1—Ag1	116.5 (3)	C8—C7—S1	107.6 (4)
C10—N2—C9	116.7 (5)	C8—C7—H7A	110.2
C10—N2—Ag1ⁱⁱⁱ	122.9 (4)	S1—C7—H7A	110.2
C9—N2—Ag1ⁱⁱⁱ	120.1 (4)	C8—C7—H7B	110.2
O2'—N3—O1'	127.6 (17)	S1—C7—H7B	110.2
O3—N3—O1	130.1 (11)	H7A—C7—H7B	108.5
O3—N3—O2	114.9 (11)	C9—C8—C12	118.2 (5)
O1—N3—O2	113.4 (12)	C9—C8—C7	120.6 (5)
O2'—N3—O3'	117.6 (16)	C12—C8—C7	121.1 (5)
O1'—N3—O3'	114.7 (13)	N2—C9—C8	123.3 (5)
N3—O1'—Ag1	118.8 (14)	N2—C9—H9	118.3
N1—C1—C2	123.8 (5)	C8—C9—H9	118.3
N1—C1—H1	118.1	N2—C10—C11	123.9 (6)
C2—C1—H1	118.1	N2—C10—H10	118.1
C3—C2—C1	117.3 (5)	C11—C10—H10	118.1
C3—C2—C6	123.5 (5)	C12—C11—C10	118.4 (6)
C1—C2—C6	119.2 (5)	C12—C11—H11	120.8
C4—C3—C2	120.0 (5)	C10—C11—H11	120.8
C4—C3—H3	120.0	C11—C12—C8	119.5 (6)
C2—C3—H3	120.0	C11—C12—H12	120.3
C3—C4—C5	118.2 (5)	C8—C12—H12	120.3

O2'—N3—O1'—Ag1	−73 (3)	Ag1ⁱⁱ—S1—C6—C2	10.9 (4)
O3'—N3—O1'—Ag1	107.3 (14)	C6—S1—C7—C8	173.0 (4)
C5—N1—C1—C2	−1.3 (7)	Ag1ⁱⁱ—S1—C7—C8	60.0 (4)
Ag1—N1—C1—C2	−178.0 (4)	S1—C7—C8—C9	−110.0 (5)
N1—C1—C2—C3	0.5 (7)	S1—C7—C8—C12	70.4 (6)
N1—C1—C2—C6	180.0 (5)	C10—N2—C9—C8	−0.5 (8)
C1—C2—C3—C4	0.5 (7)	Ag1ⁱⁱⁱ—N2—C9—C8	173.4 (4)
C6—C2—C3—C4	−178.9 (5)	C12—C8—C9—N2	−0.8 (8)
C2—C3—C4—C5	−0.7 (8)	C7—C8—C9—N2	179.6 (5)
C1—N1—C5—C4	1.2 (8)	C9—N2—C10—C11	1.5 (9)
Ag1—N1—C5—C4	178.2 (4)	Ag1ⁱⁱⁱ—N2—C10—C11	−172.3 (5)
C3—C4—C5—N1	−0.2 (8)	N2—C10—C11—C12	−1.0 (10)
C3—C2—C6—S1	62.6 (6)	C10—C11—C12—C8	−0.5 (9)
C1—C2—C6—S1	−116.9 (4)	C9—C8—C12—C11	1.3 (8)
C7—S1—C6—C2	−99.9 (4)	C7—C8—C12—C11	−179.1 (5)

Symmetry codes: (i) x−1/2, y+1/2, z; (ii) −x+1/2, −y+1/2, −z+1; (iii) x+1/2, y−1/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O2	0.93	2.59	2.924 (12)	102
C5—H5···O2^iv	0.93	2.60	3.318 (14)	135
C6—H6A···O2^v	0.97	2.52	3.464 (14)	163
C6—H6B···O2′^vi	0.97	2.60	3.44 (2)	145
C7—H7B···O3′^v	0.97	2.38	3.233 (15)	147
C9—H9···O1ⁱⁱⁱ	0.93	2.49	3.221 (18)	136
C12—H12···O3^vii	0.93	2.45	3.256 (12)	145

Symmetry codes: (iii) x+1/2, y−1/2, z; (iv) −x+1/2, −y+3/2, −z+1; (v) −x+1/2, y−1/2, −z+1/2; (vi) x, y−1, z; (vii) −x+1/2, y−3/2, −z+1/2.

Funding information

This research was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (NRF-2015R1D1A3A01020410 and NRF-2016R1D1A1B01012630).

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