Crystal structure of a helical silver(I) coordination polymer based on an unsymmetrical dipyridyl ligand: catena-poly[[silver(I)-μ-N-(pyridin-4-ylmeth­yl)pyridine-3-amine-κ2N:N′] tetra­fluorido­borate methanol hemisolvate]

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

doi:10.1107/S205698901501837X

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ISSN: 2056-9890

Volume 71| Part 11| November 2015| Pages 1287-1289

https://doi.org/10.1107/S205698901501837X

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Crystal structure of a helical silver(I) coordination polymer based on an unsymmetrical dipyridyl ligand: catena-poly[[silver(I)-μ-N-(pyridin-4-ylmethyl)pyridine-3-amine-κ²N:N′] tetrafluoridoborate methanol hemisolvate]

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, South Korea, ^bDivision of Science Education, Kangwon National University, Chuncheon 24341, South Korea, and ^cResearch Institute of Natural Science, Gyeongsang National University, Jinju 52828, South Korea
^*Correspondence e-mail: kangy@kangwon.ac.kr, kmpark@gnu.ac.kr

Edited by V. V. Chernyshev, Moscow State University, Russia (Received 23 September 2015; accepted 1 October 2015; online 7 October 2015)

The asymmetric unit of the title compound, {[AgL]·BF₄·0.5CH₃OH}_n, L = N-(pyridin-4-ylmethyl)pyridine-3-amine, C₁₁H₁₁N₃, contains one Ag^I ion, one ligand L, one tetrafluoridoborate anion disordered over two orientations in a 0.669 (13):0.331 (13) ratio and one half of a methanol solvent molecule situated on an inversion center. Each Ag^I ion is coordinated by two N atoms from two L ligands in a distorted linear geometry [N—Ag—N = 174.70 (19)°]. Each L ligand bridges two Ag^I ions, thus forming polymeric helical chains propagating in [010]. In the crystal, Ag⋯Ag [3.3369 (10) Å] and π–π interactions between the aromatic rings [centroid-to-centroid distance = 3.676 (4) Å] link these chains into layers parallel to (10-1). Ag⋯F and weak N(C)—H⋯F interactions further consolidate the crystal packing.

Keywords: crystal structure; silver(I) tetrafluoridoborate; unsymmetrical dipyridyl ligand; helical coordination polymer.

CCDC reference: 1428966

1. Chemical context

In supramolecular chemistry and material science, infinite helical coordination polymers have attracted particular interest for the past two decades because of their fascinating architecture, their similarities to biological systems and their potential applications in catalysis and optical materials (Leong & Vittal, 2011 ; Wang et al., 2012 ; Zhang et al., 2009 ). Despite numerous examples of helical coordination polymers, the rational strategy of construction of helical coordination polymers is still constrained by our poor understanding of the role of the metal ions and spacer ligands. Nevertheless, the combination of a silver ion with a linear coordination geometry and flexible unsymmetrical dipyridyl ligands composed of two terminal pyridines with different substituted-nitrogen positions is one of the most promising strategies for achieving helical coordination polymers. Our group and that of Gao have already reported helical coordination polymers obtained through the reactions of silver salts and some unsymmetrical dipyridyl ligands such as N-(pyridin-3-ylmethyl)pyridine-2-amine (Moon & Park, 2013 ), N-(pyridin-2-ylmethyl)pyridine-3-amine (Moon & Park, 2014 ) and N-(pyridin-4-ylmethyl)pyridine-3-amine (Moon et al., 2014 ; Lee et al., 2015 ; Zhang et al., 2013 ). Herein, we report the crystal structure of the title compound prepared by the reaction of silver tetrafluoridoborate with the unsymmetrical dipyridyl ligand, N-(pyridin-4-ylmethyl)pyridine-3-amine (L), synthesized according to the procedure described by Lee et al. (2013 ). The structure of the title compound is related to those of the Ag^I coordination polymers with three different counter-anions such as nitrate, perchlorate and trifluoromethanesulfonate (Moon et al., 2014; Lee et al., 2015; Zhang et al., 2013).

2. Structural commentary

The molecular components of the title structure are shown in Fig. 1. The asymmetric unit consists of one Ag^I ion, one L ligand, one tetrafluoridoborate anion and one half of a methanol molecule. Each Ag^I ion is coordinated by two pyridine N atoms from two symmetry-related ligands in a geometry which is slightly distorted from linear [N1—Ag1—N3 = 174.70 (19)°], forming an infinite helical coordination polymer. The helical chain propagates along [010] (Fig. 2) with a pitch length of 15.6485 (14) Å, shorter than that [16.7871 (8) Å] of the nitrate-containing Ag^I coordination polymer reported by Moon et al. (2014). The two pyridine rings coordinating the Ag^I ion are tilted by 13.8 (3)° with respect to each other. The two pyridine rings in the L ligand are almost perpendicular, the dihedral angle between their mean planes being 89.34 (15)°.

Figure 1
A view of the molecular structure of the title compound with the atom numbering. Displacement ellipsoids are drawn at the 30% probability level. The F atoms of the tetrafluoridoborate group are disordered over two sets of sites with refined site-occupancy factors of 0.669 (13) (part A) and 0.331 (13) (part B). The disordered methanol solvent molecule is omitted for clarity. [Symmetry codes: (i) − x + $[{3\over 2}]$ , y − $[{1\over 2}]$ , − z + $[{3\over 2}]$ ; (ii) − x + $[{3\over 2}]$ , y + $[{1\over 2}]$ , − z + $[{3\over 2}]$ .]

Figure 2
The two-dimensional supramolecular network formed through Ag⋯Ag (yellow dashed lines) and π–π (black dashed lines) interactions. The disordered methanol molecules and tetrafluoridoborate anions are omitted for clarity.

3. Supramolecular features

In the crystal structure, symmetry-related right- and left-handed helical chains are arranged alternately through Ag⋯Ag [3.3369 (10) Å] and Ag⋯F interactions [Ag1⋯F1A = 2.84 (2), Ag1⋯F1B = 2.815 (15) and Ag1⋯F4B (−x + 1, −y, −z + 1) = 2.879 (10) Å] and π–π interactions between the pyridine rings of adjacent helical chains [centroid-to-centroid distance = 3.676 (4) Å], resulting in the formation of a two-dimensional supramolecular network parallel to the (10 $[\overline{1}]$ ) plane (Fig. 2). Furthermore, several N—H⋯F and C—H⋯F hydrogen bonds (Table 1) between the helical chains and the anions contribute to stabilization of the crystal structure.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯F2Aⁱ	0.88	2.10	2.887 (9)	148
N2—H2⋯F2Bⁱ	0.88	2.58	3.357 (17)	148
C6—H6A⋯F4Aⁱⁱ	0.99	2.39	3.259 (12)	146
C10—H10⋯F4Aⁱⁱⁱ	0.95	2.41	3.318 (19)	159
C12—H12B⋯F1A	0.98	2.14	3.08 (4)	160
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x+1, y, z; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

4. Database survey

The non-solvated structures of the silver(I) nitrate and perchlorate complexes of the same ligand have been reported by Zhang et al. (2013). Our group has reported the solvated form of the silver nitrate complex with an L ligand (Moon et al., 2014). These complexes adopt single-stranded helical structures. Our group has also reported the silver trifluoridomethanesulfonate complex with an L ligand, which displays a double-stranded helical structure (Lee et al., 2015).

5. Synthesis and crystallization

The N-(pyridin-4-ylmethyl)pyridine-3-amine ligand was synthesized according to a literature method (Lee et al., 2013). X-ray quality single crystals of the title compound were obtained by slow evaporation of a methanol solution of the ligand with AgBF₄ in the molar ratio 1:1.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The methanol solvent molecule resides on an inversion centre. Therefore the C12/O12 atoms were refined at the same sites with site occupancy factors of 0.5 using EXYZ/EADP constraints. All H atoms were positioned geometrically and refined using a riding model, with d(C—H) = 0.95 Å for Csp²—H, 0.88 Å for amine N—H, 0.84 Å for hydroxyl O—H, 0.98 Å for methyl C—H and 0.99 Å for methylene C—H. For all H atoms U_iso(H) = 1.2–1.5U_eq of the parent atom.

Table 2
Experimental details

Crystal data
Chemical formula	[Ag(C₁₁H₁₁N₃)](BF₄)·0.5CH₄O
M_r	395.93
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	9.2597 (8), 15.6485 (14), 10.3574 (10)
β (°)	107.185 (2)
V (Å³)	1433.8 (2)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	1.45
Crystal size (mm)	0.50 × 0.40 × 0.40

Data collection
Diffractometer	Bruker SMART CCD area detector
Absorption correction	Multi-scan (SADABS; Bruker, 2000 )
T_min, T_max	0.531, 0.595
No. of measured, independent and observed [I > 2σ(I)] reflections	8014, 2821, 1883
R_int	0.077
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.167, 1.02
No. of reflections	2821
No. of parameters	227
No. of restraints	31
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.18, −0.70
Computer programs: SMART and SAINT-Plus (Bruker, 2000), SHELXS97, SHELXL97 and SHELXTL (Sheldrick, 2008 ) and DIAMOND (Brandenburg, 2005 ).

Supporting information

CCDC reference: 1428966

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S205698901501837X/cv5498sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698901501837X/cv5498Isup2.hkl

checkCIF report

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker, 2000); data reduction: SAINT-Plus (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2005); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

catena-Poly[[silver(I)-µ-N-(pyridine-4-ylmethyl)pyridine-3-amine-κ²N:N'] tetrafluoridoborate methanol hemisolvate] top

Crystal data top

[Ag(C₁₁H₁₁N₃)](BF₄)·0.5CH₄O	F(000) = 780
M_r = 395.93	D_x = 1.834 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2696 reflections
a = 9.2597 (8) Å	θ = 2.4–24.7°
b = 15.6485 (14) Å	µ = 1.45 mm⁻¹
c = 10.3574 (10) Å	T = 173 K
β = 107.185 (2)°	Block, colorless
V = 1433.8 (2) Å³	0.50 × 0.40 × 0.40 mm
Z = 4

Data collection top

Bruker SMART CCD area detector diffractometer	2821 independent reflections
Radiation source: fine-focus sealed tube	1883 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.077
φ and ω scans	θ_max = 26.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→11
T_min = 0.531, T_max = 0.595	k = −17→19
8014 measured reflections	l = −10→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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.167	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.1027P)²] where P = (F_o² + 2F_c²)/3
2821 reflections	(Δ/σ)_max = 0.001
227 parameters	Δρ_max = 1.18 e Å⁻³
31 restraints	Δρ_min = −0.70 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.

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 > 2sigma(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	Occ. (<1)
Ag1	0.67175 (6)	−0.04405 (3)	0.54637 (6)	0.0593 (3)
B1	0.6447 (9)	0.1230 (5)	0.8147 (8)	0.077 (3)
F1A	0.733 (3)	0.0831 (17)	0.751 (3)	0.217 (10)	0.669 (13)
F2A	0.7295 (8)	0.1786 (5)	0.9050 (9)	0.094 (3)	0.669 (13)
F3A	0.6034 (13)	0.0671 (7)	0.9030 (10)	0.127 (4)	0.669 (13)
F4A	0.5186 (12)	0.1597 (13)	0.7407 (16)	0.197 (8)	0.669 (13)
F1B	0.735 (2)	0.0733 (11)	0.762 (2)	0.072 (5)	0.331 (13)
F2B	0.6706 (19)	0.2035 (7)	0.7697 (18)	0.095 (6)	0.331 (13)
F3B	0.680 (3)	0.1190 (19)	0.9487 (12)	0.143 (9)	0.331 (13)
F4B	0.533 (2)	0.0941 (12)	0.7100 (13)	0.103 (8)	0.331 (13)
N1	0.7799 (6)	0.0402 (3)	0.4442 (6)	0.0510 (13)
N2	1.1086 (8)	0.1806 (4)	0.5210 (8)	0.0774 (19)
H2	1.1636	0.2066	0.4765	0.093*
N3	0.9214 (6)	0.3630 (3)	0.8522 (6)	0.0556 (13)
C1	0.8958 (7)	0.0881 (4)	0.5113 (7)	0.0515 (15)
H1	0.9210	0.0901	0.6071	0.062*
C2	0.9820 (7)	0.1356 (4)	0.4482 (7)	0.0554 (16)
C3	0.9445 (10)	0.1342 (5)	0.3107 (8)	0.070 (2)
H3	1.0018	0.1660	0.2650	0.083*
C4	0.8219 (11)	0.0860 (5)	0.2380 (8)	0.077 (2)
H4	0.7934	0.0851	0.1420	0.092*
C5	0.7414 (9)	0.0390 (4)	0.3067 (8)	0.0639 (19)
H5	0.6580	0.0053	0.2572	0.077*
C6	1.1541 (8)	0.1869 (4)	0.6647 (10)	0.071 (2)
H6A	1.2613	0.2049	0.6947	0.085*
H6B	1.1491	0.1290	0.7015	0.085*
C7	1.0659 (7)	0.2468 (4)	0.7280 (8)	0.0576 (17)
C8	0.9678 (8)	0.3085 (4)	0.6527 (8)	0.0617 (18)
H8	0.9486	0.3119	0.5576	0.074*
C9	0.8995 (7)	0.3642 (4)	0.7187 (8)	0.0585 (17)
H9	0.8329	0.4059	0.6666	0.070*
C10	1.0124 (8)	0.3026 (4)	0.9239 (8)	0.0656 (19)
H10	1.0274	0.2992	1.0186	0.079*
C11	1.0858 (8)	0.2446 (4)	0.8627 (8)	0.0621 (18)
H11	1.1509	0.2028	0.9165	0.074*
C12	1.022 (2)	0.0409 (10)	0.980 (3)	0.256 (12)	0.50
H12A	1.0264	0.0829	1.0514	0.385*	0.50
H12B	0.9477	0.0594	0.8961	0.385*	0.50
H12C	1.1217	0.0362	0.9658	0.385*	0.50
O12	1.022 (2)	0.0409 (10)	0.980 (3)	0.256 (12)	0.50
H12	1.1101	0.0377	0.9735	0.385*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.0566 (4)	0.0409 (3)	0.0845 (5)	0.0059 (2)	0.0271 (3)	0.0069 (2)
B1	0.081 (6)	0.077 (6)	0.064 (6)	−0.011 (5)	0.010 (5)	−0.004 (5)
F1A	0.237 (13)	0.226 (13)	0.203 (13)	0.004 (9)	0.088 (9)	−0.034 (9)
F2A	0.090 (5)	0.079 (5)	0.120 (8)	−0.025 (4)	0.043 (5)	−0.053 (5)
F3A	0.138 (9)	0.147 (9)	0.090 (7)	−0.053 (7)	0.026 (6)	−0.008 (6)
F4A	0.102 (9)	0.28 (2)	0.173 (12)	0.070 (12)	−0.014 (8)	0.009 (14)
F1B	0.112 (9)	0.053 (7)	0.066 (7)	−0.005 (6)	0.050 (6)	−0.034 (5)
F2B	0.108 (10)	0.057 (7)	0.113 (10)	−0.006 (6)	0.022 (7)	−0.013 (6)
F3B	0.148 (12)	0.155 (13)	0.125 (11)	0.010 (9)	0.037 (9)	−0.024 (9)
F4B	0.154 (19)	0.090 (12)	0.057 (9)	−0.039 (12)	0.015 (10)	−0.029 (8)
N1	0.049 (3)	0.035 (3)	0.069 (4)	0.007 (2)	0.018 (3)	0.001 (2)
N2	0.074 (4)	0.048 (3)	0.127 (6)	0.000 (3)	0.054 (4)	−0.002 (4)
N3	0.051 (3)	0.038 (3)	0.078 (4)	−0.004 (2)	0.018 (3)	−0.004 (3)
C1	0.057 (4)	0.038 (3)	0.062 (4)	0.013 (3)	0.022 (3)	−0.001 (3)
C2	0.058 (4)	0.035 (3)	0.081 (5)	0.011 (3)	0.032 (4)	0.003 (3)
C3	0.092 (6)	0.049 (4)	0.079 (5)	0.025 (4)	0.042 (4)	0.021 (4)
C4	0.115 (7)	0.061 (5)	0.060 (5)	0.025 (5)	0.034 (5)	0.013 (4)
C5	0.073 (5)	0.047 (4)	0.067 (5)	0.015 (3)	0.014 (4)	−0.003 (3)
C6	0.051 (4)	0.045 (4)	0.111 (7)	0.006 (3)	0.014 (4)	−0.019 (4)
C7	0.046 (3)	0.036 (3)	0.085 (5)	−0.004 (3)	0.011 (3)	−0.001 (3)
C8	0.056 (4)	0.048 (4)	0.074 (5)	0.013 (3)	0.009 (3)	−0.008 (3)
C9	0.047 (3)	0.044 (3)	0.078 (5)	0.006 (3)	0.011 (3)	0.001 (3)
C10	0.072 (4)	0.042 (4)	0.074 (5)	−0.008 (3)	0.008 (4)	0.010 (3)
C11	0.054 (4)	0.035 (3)	0.092 (6)	0.002 (3)	0.013 (4)	0.008 (3)
C12	0.145 (14)	0.29 (3)	0.36 (3)	−0.016 (16)	0.106 (15)	−0.01 (2)
O12	0.145 (14)	0.29 (3)	0.36 (3)	−0.016 (16)	0.106 (15)	−0.01 (2)

Geometric parameters (Å, º) top

Ag1—N1	2.118 (5)	C2—C3	1.362 (11)
Ag1—N3ⁱ	2.121 (5)	C3—C4	1.386 (12)
Ag1—Ag1ⁱⁱ	3.3369 (10)	C3—H3	0.9500
B1—F4A	1.324 (8)	C4—C5	1.384 (11)
B1—F3B	1.330 (10)	C4—H4	0.9500
B1—F4B	1.336 (9)	C5—H5	0.9500
B1—F2A	1.348 (11)	C6—C7	1.514 (9)
B1—F1A	1.349 (10)	C6—H6A	0.9900
B1—F1B	1.367 (9)	C6—H6B	0.9900
B1—F2B	1.388 (9)	C7—C11	1.352 (10)
B1—F3A	1.398 (8)	C7—C8	1.396 (9)
N1—C1	1.325 (9)	C8—C9	1.371 (10)
N1—C5	1.363 (10)	C8—H8	0.9500
N2—C2	1.385 (9)	C9—H9	0.9500
N2—C6	1.425 (11)	C10—C11	1.394 (10)
N2—H2	0.8800	C10—H10	0.9500
N3—C10	1.336 (8)	C11—H11	0.9500
N3—C9	1.337 (9)	C12—C12^iv	1.44 (3)
N3—Ag1ⁱⁱⁱ	2.121 (5)	C12—H12A	0.9800
C1—C2	1.388 (9)	C12—H12B	0.9800
C1—H1	0.9500	C12—H12C	0.9800

N1—Ag1—N3ⁱ	174.70 (19)	N1—C1—H1	118.5
N1—Ag1—Ag1ⁱⁱ	98.63 (14)	C2—C1—H1	118.5
N3ⁱ—Ag1—Ag1ⁱⁱ	86.18 (14)	C3—C2—N2	119.4 (7)
F4A—B1—F3B	121.9 (14)	C3—C2—C1	118.6 (7)
F4A—B1—F4B	48.5 (9)	N2—C2—C1	121.9 (7)
F3B—B1—F4B	136.5 (18)	C2—C3—C4	119.5 (7)
F4A—B1—F2A	110.8 (11)	C2—C3—H3	120.3
F3B—B1—F2A	52.5 (14)	C4—C3—H3	120.3
F4B—B1—F2A	159.0 (12)	C5—C4—C3	119.3 (7)
F4A—B1—F1A	118.5 (16)	C5—C4—H4	120.4
F3B—B1—F1A	119.4 (17)	C3—C4—H4	120.4
F4B—B1—F1A	83.3 (16)	N1—C5—C4	121.0 (7)
F2A—B1—F1A	109.0 (14)	N1—C5—H5	119.5
F4A—B1—F1B	123.6 (14)	C4—C5—H5	119.5
F3B—B1—F1B	113.5 (15)	N2—C6—C7	117.7 (6)
F4B—B1—F1B	84.3 (15)	N2—C6—H6A	107.9
F2A—B1—F1B	110.2 (10)	C7—C6—H6A	107.9
F1A—B1—F1B	8 (2)	N2—C6—H6B	107.9
F4A—B1—F2B	67.8 (10)	C7—C6—H6B	107.9
F3B—B1—F2B	112.2 (17)	H6A—C6—H6B	107.2
F4B—B1—F2B	101.7 (11)	C11—C7—C8	117.5 (7)
F2A—B1—F2B	61.5 (9)	C11—C7—C6	120.3 (6)
F1A—B1—F2B	93.7 (15)	C8—C7—C6	122.1 (8)
F1B—B1—F2B	101.3 (12)	C9—C8—C7	118.7 (7)
F4A—B1—F3A	106.6 (11)	C9—C8—H8	120.6
F3B—B1—F3A	47.1 (14)	C7—C8—H8	120.6
F4B—B1—F3A	91.4 (10)	N3—C9—C8	123.8 (6)
F2A—B1—F3A	99.5 (7)	N3—C9—H9	118.1
F1A—B1—F3A	110.8 (14)	C8—C9—H9	118.1
F1B—B1—F3A	102.9 (12)	N3—C10—C11	121.3 (7)
F2B—B1—F3A	153.5 (11)	N3—C10—H10	119.3
C1—N1—C5	118.6 (6)	C11—C10—H10	119.3
C1—N1—Ag1	121.3 (5)	C7—C11—C10	121.1 (6)
C5—N1—Ag1	119.8 (5)	C7—C11—H11	119.5
C2—N2—C6	123.0 (6)	C10—C11—H11	119.5
C2—N2—H2	118.5	C12^iv—C12—H12A	109.5
C6—N2—H2	118.5	C12^iv—C12—H12B	109.5
C10—N3—C9	117.5 (6)	H12A—C12—H12B	109.5
C10—N3—Ag1ⁱⁱⁱ	119.4 (5)	C12^iv—C12—H12C	109.5
C9—N3—Ag1ⁱⁱⁱ	122.9 (4)	H12A—C12—H12C	109.5
N1—C1—C2	123.0 (7)	H12B—C12—H12C	109.5

N3ⁱ—Ag1—N1—C1	−87 (2)	C3—C4—C5—N1	0.7 (10)
Ag1ⁱⁱ—Ag1—N1—C1	117.9 (4)	C2—N2—C6—C7	−75.9 (9)
N3ⁱ—Ag1—N1—C5	86 (2)	N2—C6—C7—C11	168.5 (6)
Ag1ⁱⁱ—Ag1—N1—C5	−69.4 (5)	N2—C6—C7—C8	−14.7 (10)
C5—N1—C1—C2	−1.5 (9)	C11—C7—C8—C9	1.2 (10)
Ag1—N1—C1—C2	171.4 (4)	C6—C7—C8—C9	−175.7 (6)
C6—N2—C2—C3	178.6 (6)	C10—N3—C9—C8	−1.6 (10)
C6—N2—C2—C1	−4.6 (10)	Ag1ⁱⁱⁱ—N3—C9—C8	175.0 (5)
N1—C1—C2—C3	1.2 (9)	C7—C8—C9—N3	0.0 (10)
N1—C1—C2—N2	−175.6 (6)	C9—N3—C10—C11	2.0 (9)
N2—C2—C3—C4	177.0 (6)	Ag1ⁱⁱⁱ—N3—C10—C11	−174.7 (5)
C1—C2—C3—C4	0.2 (10)	C8—C7—C11—C10	−0.8 (10)
C2—C3—C4—C5	−1.0 (11)	C6—C7—C11—C10	176.1 (6)
C1—N1—C5—C4	0.6 (9)	N3—C10—C11—C7	−0.8 (10)
Ag1—N1—C5—C4	−172.4 (5)

Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) −x+1, −y, −z+1; (iii) −x+3/2, y+1/2, −z+3/2; (iv) −x+2, −y, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···F2A^v	0.88	2.10	2.887 (9)	148
N2—H2···F2B^v	0.88	2.58	3.357 (17)	148
C6—H6A···F4A^vi	0.99	2.39	3.259 (12)	146
C10—H10···F4A^vii	0.95	2.41	3.318 (19)	159
C12—H12B···F1A	0.98	2.14	3.08 (4)	160

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

Acknowledgements

This work was supported by NRF projects 2015R1D1A3A01020410 and 2011–0010518.

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