catena-Poly[[silver(I)-μ-N-[(pyridin-2-yl)meth­yl]pyridine-3-amine-κ2N:N′] hexa­fluorido­phosphate]

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

doi:10.1107/S1600536814011465

metal-organic compounds

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ISSN: 2056-9890

Volume 70| Part 6| June 2014| Page m233

doi:10.1107/S1600536814011465

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catena-Poly[[silver(I)-μ-N-[(pyridin-2-yl)methyl]pyridine-3-amine-κ²N:N′] hexafluoridophosphate]

Suk-Hee Moon ^a and Ki-Min Park ^b ^*

^aDepartment of Food & Nutrition, Kyungnam College of Information and Technology, Busan 617-701, Republic of Korea, and ^bResearch Institute of Natural Sciences, Gyeongsang National University, Jinju 660-701, Republic of Korea
^*Correspondence e-mail: kmpark@gnu.ac.kr

(Received 16 May 2014; accepted 18 May 2014; online 24 May 2014)

In the title polymeric complex, {[Ag(C₁₁H₁₁N₃)]PF₆}_n, the Ag^I ion is two-coordinated in a nearly linear coordination geometry [N—Ag—N = 175.98 (9)°] by two pyridine N atoms from two symmetry-related N-[(pyridine-2-yl)methyl]pyridine-3-amine ligands. Each Ag^I ion is bridged by the ligands, forming a helical chain propagating along the b-axis direction. The right- and left-handed helical chains are alternately arranged via Ag⋯Ag [3.2639 (5) Å] and π–π stacking interactions [centroid–centroid distance = 3.523 (1) Å], resulting in the formation of a two-dimensional supramolecular network extending parallel to (101). Weak Ag⋯F interactions [longest Ag⋯F interaction = 3.153 (2) Å], as well as N—H⋯F and C—H⋯F hydrogen-bonding interactions, occur between the helical chains and the anions.

CCDC reference: 1003661

Related literature

For structures of Ag^I coordination polymers with symmetrical dipyridyl ligands, see: Lee et al. (2012 ); Leong & Vittal (2011 ); Park et al. (2010 ) and of Ag^I coordination polymers with unsymmetrical dipyridyl ligands, see: Moon & Park (2013 ); Zhang et al. (2013 ). For the synthesis of the ligand, see: Lee et al. (2013 ).

Experimental

Crystal data

[Ag(C₁₁H₁₁N₃)]PF₆
M_r = 438.07
Monoclinic, P 2₁ /n
a = 10.9978 (6) Å
b = 10.5081 (6) Å
c = 12.7559 (7) Å
β = 108.976 (1)°
V = 1394.04 (13) Å³
Z = 4
Mo Kα radiation
μ = 1.63 mm⁻¹
T = 173 K
0.25 × 0.25 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.687, T_max = 0.737
7790 measured reflections
2740 independent reflections
2509 reflections with I > 2σ(I)
R_int = 0.018

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.071
S = 1.05
2740 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.86 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯F5ⁱ	0.88	2.51	3.354 (4)	160
C4—H4⋯F1ⁱⁱ	0.95	2.52	3.336 (4)	145
C5—H5⋯F5ⁱⁱⁱ	0.95	2.55	3.447 (4)	157
C5—H5⋯F6ⁱⁱⁱ	0.95	2.43	3.280 (4)	149
C6—H6A⋯F3^iv	0.99	2.54	3.467 (4)	155
C11—H11⋯F3^v	0.95	2.49	3.397 (4)	160
Symmetry codes: (i) -x+1, -y+1, -z; (ii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) -x, -y+1, -z.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker, 2000); data reduction: SAINT-Plus; 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).

Supporting information

CCDC reference: 1003661

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536814011465/sj5402sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814011465/sj5402Isup2.hkl

checkCIF report

Comment top

Metal-organic frameworks based on silver ions and dipyridyl type ligands have been of increasing interest in coordination chemistry owing to their intriguing architectures caused by the variety of coordination geometries of the Ag(I) ions (Lee et al., 2012; Leong & Vittal, 2011; Park et al., 2010). Recently, we have reported an investigation of Ag(I) coordination polymers using unsymmetrical dipyridyl ligands with nitrogen donor atoms in different positions on the two terminal pyridines (Moon & Park, 2013; Zhang et al., 2013). In extending this work, N-(pyridine-2-ylmethyl)pyridine-3-amine as an unsymmetrical dipyridyl ligand was prepared by the reaction of 3-aminopyridine and 2-pyridinecarboxaldehyde according to a previously reported method (Lee et al., 2013). Herein we report the crystal structure of the title compound prepared by the reaction of silver hexafluorophosphate with the unsymmetrical dipyridyl ligand. The structure of the title compound is isostructural with that of the perchlorate salt (Zhang et al., 2013).

The title compound is shown in Fig. 1. The asymmetric unit contains one Ag^I cation, one N-(pyridine-2-ylmethyl)pyridine-3-amine (Lee et al., 2013) ligand and one PF₆^- anion. The Ag atom links two pyridine N atoms from two symmetry-related ligands to form a helical chain. Thus the Ag atom is two-coordinate in a slightly distorted linear coordination geometry [N–Ag–N = 175.98 (9)°]. The helical chain with a pitch length of 10.5081 (6) Å propagates along the b axis (Fig. 2). Right- and left-handed helical chains are alternately arranged via Ag···Ag [3.2639 (5) Å] and π–π stacking interactions [centroid-centroid distance = 3.523 (1) Å] between pyridine rings of the helical chains, resulting in the formation of a two-dimensional supramolecular network extending parallel to the (101) plane (Fig. 3).

The non-coordinating PF₆^- anions participate in Ag···F interactions (Ag1···F1 3.035 (2), Ag1···F3 3.041 (2), Ag1···F6ⁱⁱⁱ 3.153 (2) Å, symmetry code: (iii) 1/2 + x, 1.5 - y, 1/2 + z) (Fig. 1,3). In addition,N–H···F and C–H···F hydrogen bonds (Table 1, Fig. 3) between the helical chains and anions are also found in the crystal.

Related literature top

For structures of Ag^I coordination polymers with symmetrical dipyridyl ligands, see: Lee et al. (2012); Leong & Vittal (2011); Park et al. (2010) and of Ag^I coordination polymers with unsymmetrical dipyridyl ligands, see: Moon & Park (2013); Zhang et al. (2013). For the synthesis of the ligand, see: Lee et al. (2013).

Experimental top

The ligand (N-(pyridin-2-ylmethyl)pyridine-3-amine) was prepared according to a procedure described by Lee et al. (2013). Crystals of the title compound suitable for X-ray analysis were obtained by vapor diffusion of diethyl ether into a DMSO solution of the white precipitate afforded by the reaction of the ligand with silver(I) hexafluorophosphate in the molar ratio 1:1 in methanol.

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).

Figures top

	Fig. 1. A view of the molecular structure of the title compound, with atom numbering. Displacement ellipsoids are drawn at the 50% probability level and dashed lines present Ag···F contacts [Symmetry codes: (i) 1/2 - x, 1/2 + y, 1/2 - z; (ii) 1/2 - x, -1/2 + y, 1/2 - z].
	Fig. 2. The helical chain formed by cationic polymer of the title compound along the b axis.
	Fig. 3. The two-dimensional supramolecular structure formed through Ag···Ag and Ag···F interactions (yellow dashed lines) and π–π stacking interactions (black dashed lines). Red dashed lines present N–H···F hydrogen bonds.

catena-Poly[[silver(I)-µ-N-[(pyridin-2-yl)methyl]pyridine-3-amine-κ²N:N'] hexafluoridophosphate] top

Crystal data top

[Ag(C₁₁H₁₁N₃)]PF₆	F(000) = 856
M_r = 438.07	D_x = 2.087 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5558 reflections
a = 10.9978 (6) Å	θ = 2.6–28.3°
b = 10.5081 (6) Å	µ = 1.63 mm⁻¹
c = 12.7559 (7) Å	T = 173 K
β = 108.976 (1)°	Block, pale-yellow
V = 1394.04 (13) Å³	0.25 × 0.25 × 0.20 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2740 independent reflections
Radiation source: fine-focus sealed tube	2509 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −13→13
T_min = 0.687, T_max = 0.737	k = −12→12
7790 measured reflections	l = −15→7

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.071	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0342P)² + 2.1214P] where P = (F_o² + 2F_c²)/3
2740 reflections	(Δ/σ)_max = 0.001
199 parameters	Δρ_max = 0.86 e Å⁻³
0 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

[Ag(C₁₁H₁₁N₃)]PF₆	V = 1394.04 (13) Å³
M_r = 438.07	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.9978 (6) Å	µ = 1.63 mm⁻¹
b = 10.5081 (6) Å	T = 173 K
c = 12.7559 (7) Å	0.25 × 0.25 × 0.20 mm
β = 108.976 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2740 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2509 reflections with I > 2σ(I)
T_min = 0.687, T_max = 0.737	R_int = 0.018
7790 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.071	H-atom parameters constrained
S = 1.05	Δρ_max = 0.86 e Å⁻³
2740 reflections	Δρ_min = −0.44 e Å⁻³
199 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	0.47207 (2)	0.61822 (2)	0.412386 (18)	0.03167 (9)
N1	0.5497 (2)	0.4784 (2)	0.33275 (19)	0.0266 (5)
N2	0.4485 (3)	0.2196 (3)	0.1313 (2)	0.0369 (6)
H2	0.4838	0.1727	0.0917	0.044*
N3	0.0973 (2)	0.2683 (2)	0.01010 (19)	0.0283 (5)
C1	0.4751 (3)	0.3971 (3)	0.2586 (2)	0.0280 (6)
H1	0.3845	0.4021	0.2417	0.034*
C2	0.5256 (3)	0.3050 (3)	0.2052 (2)	0.0281 (6)
C3	0.6588 (3)	0.3014 (3)	0.2305 (3)	0.0332 (7)
H3	0.6972	0.2408	0.1956	0.040*
C4	0.7343 (3)	0.3859 (3)	0.3062 (3)	0.0343 (7)
H4	0.8252	0.3839	0.3242	0.041*
C5	0.6775 (3)	0.4734 (3)	0.3559 (2)	0.0302 (6)
H5	0.7303	0.5317	0.4079	0.036*
C6	0.3137 (3)	0.2022 (3)	0.1148 (3)	0.0346 (7)
H6A	0.3001	0.2103	0.1876	0.042*
H6B	0.2896	0.1144	0.0880	0.042*
C7	0.2236 (3)	0.2940 (3)	0.0343 (2)	0.0298 (6)
C8	0.2648 (4)	0.3970 (3)	−0.0121 (3)	0.0384 (7)
H8	0.3541	0.4145	0.0060	0.046*
C9	0.1750 (4)	0.4743 (3)	−0.0851 (3)	0.0435 (8)
H9	0.2021	0.5462	−0.1169	0.052*
C10	0.0460 (4)	0.4471 (3)	−0.1120 (3)	0.0405 (8)
H10	−0.0172	0.4982	−0.1630	0.049*
C11	0.0118 (3)	0.3428 (3)	−0.0620 (3)	0.0358 (7)
H11	−0.0770	0.3231	−0.0797	0.043*
P1	0.37249 (7)	0.77956 (8)	0.11683 (7)	0.03202 (19)
F1	0.4915 (2)	0.7903 (2)	0.22735 (18)	0.0563 (6)
F2	0.4462 (3)	0.6767 (2)	0.0700 (2)	0.0647 (7)
F3	0.31392 (19)	0.66683 (19)	0.17158 (17)	0.0455 (5)
F4	0.2950 (3)	0.8808 (2)	0.1620 (3)	0.0682 (7)
F5	0.43037 (19)	0.89076 (19)	0.06094 (19)	0.0497 (5)
F6	0.2517 (2)	0.7676 (2)	0.00672 (18)	0.0597 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.03861 (15)	0.02833 (14)	0.02926 (14)	0.00868 (9)	0.01269 (10)	−0.00213 (9)
N1	0.0309 (12)	0.0256 (12)	0.0232 (12)	0.0033 (10)	0.0087 (10)	0.0017 (9)
N2	0.0353 (14)	0.0405 (15)	0.0373 (15)	−0.0029 (11)	0.0154 (12)	−0.0149 (12)
N3	0.0383 (13)	0.0253 (12)	0.0232 (12)	−0.0064 (10)	0.0127 (10)	−0.0031 (9)
C1	0.0240 (13)	0.0315 (15)	0.0279 (15)	0.0010 (11)	0.0079 (11)	−0.0011 (12)
C2	0.0312 (14)	0.0294 (14)	0.0252 (14)	0.0015 (12)	0.0109 (12)	0.0006 (11)
C3	0.0338 (15)	0.0377 (16)	0.0325 (16)	0.0065 (13)	0.0170 (13)	−0.0004 (13)
C4	0.0246 (14)	0.0443 (18)	0.0346 (17)	0.0012 (12)	0.0105 (12)	0.0030 (13)
C5	0.0322 (15)	0.0305 (15)	0.0259 (14)	−0.0044 (12)	0.0068 (12)	0.0010 (12)
C6	0.0387 (17)	0.0321 (15)	0.0307 (16)	−0.0089 (13)	0.0080 (13)	−0.0041 (12)
C7	0.0401 (16)	0.0275 (14)	0.0232 (14)	−0.0075 (12)	0.0121 (12)	−0.0054 (11)
C8	0.0502 (19)	0.0357 (17)	0.0330 (17)	−0.0148 (14)	0.0188 (15)	−0.0047 (13)
C9	0.071 (2)	0.0301 (16)	0.0350 (18)	−0.0131 (16)	0.0240 (17)	−0.0004 (13)
C10	0.062 (2)	0.0301 (16)	0.0296 (16)	0.0037 (15)	0.0158 (15)	0.0016 (13)
C11	0.0394 (16)	0.0357 (16)	0.0316 (16)	−0.0003 (14)	0.0105 (13)	−0.0017 (13)
P1	0.0292 (4)	0.0364 (4)	0.0308 (4)	−0.0005 (3)	0.0103 (3)	0.0018 (3)
F1	0.0522 (12)	0.0657 (14)	0.0409 (12)	−0.0176 (11)	0.0013 (10)	0.0084 (10)
F2	0.0786 (17)	0.0548 (14)	0.0761 (17)	0.0126 (12)	0.0465 (14)	0.0002 (12)
F3	0.0439 (11)	0.0452 (11)	0.0473 (12)	−0.0047 (9)	0.0147 (9)	0.0107 (9)
F4	0.0735 (16)	0.0467 (13)	0.105 (2)	0.0054 (11)	0.0570 (16)	−0.0062 (12)
F5	0.0384 (11)	0.0499 (12)	0.0589 (13)	−0.0044 (9)	0.0132 (10)	0.0207 (10)
F6	0.0549 (13)	0.0640 (14)	0.0469 (12)	−0.0154 (11)	−0.0018 (10)	0.0164 (11)

Geometric parameters (Å, º) top

Ag1—N1	2.117 (2)	C5—H5	0.9500
Ag1—N3ⁱ	2.130 (2)	C6—C7	1.519 (4)
Ag1—Ag1ⁱⁱ	3.2639 (5)	C6—H6A	0.9900
N1—C1	1.340 (4)	C6—H6B	0.9900
N1—C5	1.340 (4)	C7—C8	1.378 (4)
N2—C2	1.376 (4)	C8—C9	1.381 (5)
N2—C6	1.440 (4)	C8—H8	0.9500
N2—H2	0.8800	C9—C10	1.377 (5)
N3—C11	1.334 (4)	C9—H9	0.9500
N3—C7	1.348 (4)	C10—C11	1.380 (5)
N3—Ag1ⁱⁱⁱ	2.130 (2)	C10—H10	0.9500
C1—C2	1.398 (4)	C11—H11	0.9500
C1—H1	0.9500	P1—F2	1.581 (2)
C2—C3	1.395 (4)	P1—F4	1.584 (2)
C3—C4	1.374 (4)	P1—F1	1.585 (2)
C3—H3	0.9500	P1—F6	1.594 (2)
C4—C5	1.377 (4)	P1—F5	1.604 (2)
C4—H4	0.9500	P1—F3	1.612 (2)

N1—Ag1—N3ⁱ	175.98 (9)	H6A—C6—H6B	107.4
N1—Ag1—Ag1ⁱⁱ	77.59 (6)	N3—C7—C8	121.2 (3)
N3ⁱ—Ag1—Ag1ⁱⁱ	105.17 (6)	N3—C7—C6	115.1 (2)
C1—N1—C5	119.2 (2)	C8—C7—C6	123.7 (3)
C1—N1—Ag1	122.10 (19)	C7—C8—C9	119.2 (3)
C5—N1—Ag1	118.67 (19)	C7—C8—H8	120.4
C2—N2—C6	123.9 (3)	C9—C8—H8	120.4
C2—N2—H2	118.1	C10—C9—C8	119.9 (3)
C6—N2—H2	118.1	C10—C9—H9	120.0
C11—N3—C7	118.9 (3)	C8—C9—H9	120.0
C11—N3—Ag1ⁱⁱⁱ	118.4 (2)	C9—C10—C11	117.6 (3)
C7—N3—Ag1ⁱⁱⁱ	122.7 (2)	C9—C10—H10	121.2
N1—C1—C2	122.5 (3)	C11—C10—H10	121.2
N1—C1—H1	118.8	N3—C11—C10	123.2 (3)
C2—C1—H1	118.8	N3—C11—H11	118.4
N2—C2—C3	120.4 (3)	C10—C11—H11	118.4
N2—C2—C1	122.2 (3)	F2—P1—F4	178.42 (16)
C3—C2—C1	117.4 (3)	F2—P1—F1	90.46 (15)
C4—C3—C2	119.6 (3)	F4—P1—F1	90.87 (15)
C4—C3—H3	120.2	F2—P1—F6	89.76 (15)
C2—C3—H3	120.2	F4—P1—F6	88.89 (16)
C3—C4—C5	119.6 (3)	F1—P1—F6	179.13 (13)
C3—C4—H4	120.2	F2—P1—F5	90.22 (13)
C5—C4—H4	120.2	F4—P1—F5	90.62 (13)
N1—C5—C4	121.7 (3)	F1—P1—F5	90.65 (12)
N1—C5—H5	119.1	F6—P1—F5	90.19 (12)
C4—C5—H5	119.1	F2—P1—F3	89.29 (13)
N2—C6—C7	115.6 (3)	F4—P1—F3	89.86 (12)
N2—C6—H6A	108.4	F1—P1—F3	89.85 (11)
C7—C6—H6A	108.4	F6—P1—F3	89.31 (11)
N2—C6—H6B	108.4	F5—P1—F3	179.29 (13)
C7—C6—H6B	108.4

N3ⁱ—Ag1—N1—C1	−133.0 (12)	C3—C4—C5—N1	0.3 (5)
Ag1ⁱⁱ—Ag1—N1—C1	93.3 (2)	C2—N2—C6—C7	84.6 (4)
N3ⁱ—Ag1—N1—C5	45.6 (14)	C11—N3—C7—C8	1.5 (4)
Ag1ⁱⁱ—Ag1—N1—C5	−88.1 (2)	Ag1ⁱⁱⁱ—N3—C7—C8	−175.7 (2)
C5—N1—C1—C2	1.0 (4)	C11—N3—C7—C6	−178.5 (3)
Ag1—N1—C1—C2	179.6 (2)	Ag1ⁱⁱⁱ—N3—C7—C6	4.2 (3)
C6—N2—C2—C3	168.9 (3)	N2—C6—C7—N3	172.9 (2)
C6—N2—C2—C1	−10.4 (5)	N2—C6—C7—C8	−7.1 (4)
N1—C1—C2—N2	178.3 (3)	N3—C7—C8—C9	−0.5 (5)
N1—C1—C2—C3	−1.0 (4)	C6—C7—C8—C9	179.6 (3)
N2—C2—C3—C4	−178.7 (3)	C7—C8—C9—C10	−0.9 (5)
C1—C2—C3—C4	0.6 (4)	C8—C9—C10—C11	1.1 (5)
C2—C3—C4—C5	−0.2 (5)	C7—N3—C11—C10	−1.2 (5)
C1—N1—C5—C4	−0.6 (4)	Ag1ⁱⁱⁱ—N3—C11—C10	176.1 (2)
Ag1—N1—C5—C4	−179.3 (2)	C9—C10—C11—N3	−0.1 (5)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···F5^iv	0.88	2.51	3.354 (4)	160
C4—H4···F1^v	0.95	2.52	3.336 (4)	145
C5—H5···F5^vi	0.95	2.55	3.447 (4)	157
C5—H5···F6^vi	0.95	2.43	3.280 (4)	149
C6—H6A···F3ⁱⁱⁱ	0.99	2.54	3.467 (4)	155
C11—H11···F3^vii	0.95	2.49	3.397 (4)	160

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···F5ⁱ	0.88	2.51	3.354 (4)	159.9
C4—H4···F1ⁱⁱ	0.95	2.52	3.336 (4)	144.6
C5—H5···F5ⁱⁱⁱ	0.95	2.55	3.447 (4)	156.7
C5—H5···F6ⁱⁱⁱ	0.95	2.43	3.280 (4)	149.0
C6—H6A···F3^iv	0.99	2.54	3.467 (4)	154.9
C11—H11···F3^v	0.95	2.49	3.397 (4)	160.1

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

Acknowledgements

This work was supported by NRF (2010–0022675) projects.

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