Bis{1,4-bis-[(3-butyl-imidazolium-1-yl)meth-yl]benzene}-silver(I) bis-(hexa-fluoridophosphate).

The asymmetric unit of the title complex, [Ag(2)(C(22)H(30)N(4))(2)](PF(6))(2), consists of one Ag(I) ion, one 1,4-bis-[(3-butyl-imidazolium-1-yl)meth-yl]benzene ligand and one discrete hexa-fluoridophosphate anion. The formula unit is generated by an inversion center. The unique Ag(I) ion is coordinated by two C atoms of two heterocyclic carbene ligands in an essentially linear geometry. In the crystal structure, cations and anions are linked through weak C-H⋯F hydrogen bonds, forming a three-dimensional network.

Related literature

For applications of N-heterocyclic carbenes, see: Tryg et al. (2005 ▶); Herrmann (2002 ▶); Herrmann et al. (1998 ▶); McGuinness et al. (1999 ▶); Tominaga et al. (2004 ▶); Magill et al. (2001 ▶); Yongbo et al. (2008 ▶); Garrison & Youngs (2005 ▶); Kascatan-Nebioglu et al. (2007 ▶); Özdemir et al. (2010 ▶); Medvetz et al. (2008 ▶); Catalano & Malwitz (2003 ▶). For a related structure, see: Chen & Liu (2003 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

[Ag2(C22H30N4)2](PF6)2

M = 1206.68

Triclinic,

a = 11.3636 (15) Å

b = 11.4119 (15) Å

c = 11.9918 (15) Å

α = 63.528 (2)°

β = 89.335 (2)°

γ = 65.811 (2)°

V = 1241.7 (3) Å3

Z = 1

Mo Kα radiation

μ = 0.94 mm−1

T = 100 K

0.24 × 0.14 × 0.08 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.806, T max = 0.930

25433 measured reflections

7142 independent reflections

6512 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.161

S = 1.16

7142 reflections

309 parameters

H-atom parameters constrained

Δρmax = 3.16 e Å−3

Δρmin = −1.23 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810036524/lh5130sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810036524/lh5130Isup2.hkl

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

[Ag2(C22H30N4)2](PF6)2	Z = 1
Mr = 1206.68	F(000) = 612
Triclinic, P1	Dx = 1.614 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.3636 (15) Å	Cell parameters from 9946 reflections
b = 11.4119 (15) Å	θ = 2.5–30.1°
c = 11.9918 (15) Å	µ = 0.94 mm−1
α = 63.528 (2)°	T = 100 K
β = 89.335 (2)°	Block, colourless
γ = 65.811 (2)°	0.24 × 0.14 × 0.08 mm
V = 1241.7 (3) Å3

Bruker APEXII DUO CCD area-detector diffractometer	7142 independent reflections
Radiation source: fine-focus sealed tube	6512 reflections with I > 2σ(I)
graphite	Rint = 0.035
φ and ω scans	θmax = 30.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→15
Tmin = 0.806, Tmax = 0.930	k = −16→16
25433 measured reflections	l = −16→16

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161	H-atom parameters constrained
S = 1.16	w = 1/[σ2(Fo2) + (0.0678P)2 + 6.8955P] where P = (Fo2 + 2Fc2)/3
7142 reflections	(Δ/σ)max < 0.001
309 parameters	Δρmax = 3.16 e Å−3
0 restraints	Δρmin = −1.23 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

	x	y	z	Uiso*/Ueq
Ag1	0.46248 (3)	0.12904 (3)	0.32515 (3)	0.01570 (10)
N1	0.2537 (4)	0.4313 (4)	0.2939 (3)	0.0193 (7)
N2	0.1692 (4)	0.2838 (4)	0.3325 (3)	0.0185 (7)
N3	0.2430 (3)	1.0310 (4)	−0.3191 (3)	0.0170 (6)
N4	0.3348 (4)	1.1721 (4)	−0.3546 (3)	0.0172 (6)
C1	0.3370 (5)	0.5534 (5)	0.0323 (4)	0.0238 (9)
H1A	0.3746	0.4529	0.0615	0.029*
C2	0.3085 (5)	0.6488 (5)	−0.0971 (4)	0.0237 (9)
H2A	0.3260	0.6117	−0.1538	0.028*
C3	0.2540 (4)	0.7998 (5)	−0.1432 (4)	0.0176 (7)
C4	0.2269 (5)	0.8525 (5)	−0.0564 (4)	0.0221 (8)
H4A	0.1903	0.9529	−0.0855	0.026*
C5	0.2544 (5)	0.7555 (5)	0.0743 (4)	0.0214 (8)
H5A	0.2349	0.7922	0.1311	0.026*
C6	0.3102 (4)	0.6055 (4)	0.1198 (4)	0.0182 (7)
C7	0.3438 (5)	0.4986 (5)	0.2612 (4)	0.0212 (8)
H7A	0.4339	0.4226	0.2846	0.025*
H7B	0.3375	0.5499	0.3090	0.025*
C8	0.2850 (4)	0.2935 (4)	0.3183 (3)	0.0138 (6)
C9	0.1215 (5)	0.5068 (5)	0.2917 (4)	0.0239 (9)
H9A	0.0778	0.6033	0.2761	0.029*
C10	0.0679 (5)	0.4132 (5)	0.3166 (4)	0.0241 (9)
H10A	−0.0192	0.4324	0.3219	0.029*
C11	0.1508 (5)	0.1543 (5)	0.3571 (4)	0.0230 (8)
H11A	0.0978	0.1383	0.4212	0.028*
H11B	0.2362	0.0685	0.3908	0.028*
C12	0.0843 (5)	0.1712 (5)	0.2381 (4)	0.0247 (9)
H12A	−0.0006	0.2576	0.2044	0.030*
H12B	0.0682	0.0869	0.2616	0.030*
C13	0.1641 (5)	0.1852 (6)	0.1332 (5)	0.0304 (10)
H13A	0.1737	0.2743	0.1038	0.036*
H13B	0.2516	0.1027	0.1680	0.036*
C14	0.0986 (7)	0.1891 (8)	0.0216 (6)	0.0434 (14)
H14A	0.1528	0.1942	−0.0407	0.065*
H14B	0.0139	0.2737	−0.0160	0.065*
H14C	0.0874	0.1019	0.0506	0.065*
C15	0.2246 (4)	0.9007 (5)	−0.2858 (4)	0.0199 (8)
H15A	0.2817	0.8464	−0.3245	0.024*
H15B	0.1342	0.9315	−0.3213	0.024*
C16	0.3620 (4)	1.0335 (5)	−0.3299 (4)	0.0186 (7)
C17	0.1448 (4)	1.1638 (5)	−0.3387 (4)	0.0229 (8)
H17A	0.0565	1.1870	−0.3363	0.027*
C18	0.2016 (4)	1.2543 (5)	−0.3621 (4)	0.0227 (8)
H18A	0.1600	1.3516	−0.3796	0.027*
C19	0.4337 (5)	1.2264 (5)	−0.3649 (4)	0.0220 (8)
H19A	0.4153	1.3055	−0.4508	0.026*
H19B	0.5203	1.1479	−0.3498	0.026*
C20	0.4346 (6)	1.2817 (6)	−0.2701 (5)	0.0320 (10)
H20A	0.5015	1.3158	−0.2814	0.038*
H20B	0.3500	1.3657	−0.2911	0.038*
C21	0.4601 (6)	1.1718 (6)	−0.1314 (5)	0.0320 (10)
H21A	0.5518	1.0988	−0.1039	0.038*
H21B	0.4060	1.1219	−0.1217	0.038*
C22	0.4300 (6)	1.2429 (6)	−0.0469 (5)	0.0317 (10)
H22A	0.4439	1.1698	0.0396	0.048*
H22B	0.3398	1.3169	−0.0748	0.048*
H22C	0.4872	1.2871	−0.0519	0.048*
P1	0.76781 (11)	0.28501 (11)	0.51153 (10)	0.0165 (2)
F1	0.8121 (5)	0.2072 (4)	0.6636 (3)	0.0521 (11)
F2	0.6958 (3)	0.1871 (4)	0.5238 (4)	0.0452 (9)
F3	0.7303 (4)	0.3610 (3)	0.3605 (3)	0.0399 (8)
F4	0.8417 (3)	0.3835 (3)	0.4983 (3)	0.0347 (7)
F5	0.6356 (3)	0.4085 (3)	0.5124 (3)	0.0326 (7)
F6	0.9021 (3)	0.1590 (3)	0.5128 (3)	0.0294 (6)

	U11	U22	U33	U12	U13	U23
Ag1	0.01635 (15)	0.01335 (14)	0.01699 (14)	−0.00615 (11)	0.00410 (10)	−0.00754 (11)
N1	0.0274 (18)	0.0148 (15)	0.0154 (14)	−0.0088 (14)	0.0061 (13)	−0.0076 (12)
N2	0.0216 (17)	0.0157 (15)	0.0168 (15)	−0.0091 (13)	0.0085 (13)	−0.0063 (12)
N3	0.0173 (16)	0.0161 (15)	0.0147 (14)	−0.0069 (13)	0.0025 (12)	−0.0058 (12)
N4	0.0215 (17)	0.0127 (14)	0.0159 (14)	−0.0080 (13)	0.0058 (12)	−0.0056 (12)
C1	0.036 (2)	0.0166 (18)	0.0178 (18)	−0.0101 (17)	0.0053 (16)	−0.0090 (15)
C2	0.035 (2)	0.0196 (19)	0.0167 (17)	−0.0111 (18)	0.0043 (16)	−0.0101 (16)
C3	0.0198 (18)	0.0199 (18)	0.0152 (16)	−0.0115 (15)	0.0034 (14)	−0.0080 (14)
C4	0.030 (2)	0.0160 (18)	0.0188 (18)	−0.0100 (16)	0.0060 (16)	−0.0081 (15)
C5	0.031 (2)	0.0185 (18)	0.0179 (17)	−0.0114 (17)	0.0064 (16)	−0.0110 (15)
C6	0.024 (2)	0.0165 (17)	0.0159 (16)	−0.0113 (15)	0.0051 (14)	−0.0074 (14)
C7	0.032 (2)	0.0172 (18)	0.0157 (17)	−0.0124 (17)	0.0034 (15)	−0.0077 (15)
C8	0.0168 (17)	0.0095 (15)	0.0122 (15)	−0.0040 (13)	0.0044 (12)	−0.0047 (12)
C9	0.029 (2)	0.0188 (19)	0.0211 (19)	−0.0084 (17)	0.0115 (16)	−0.0096 (16)
C10	0.024 (2)	0.0195 (19)	0.024 (2)	−0.0060 (16)	0.0102 (16)	−0.0106 (16)
C11	0.028 (2)	0.0199 (19)	0.0218 (19)	−0.0134 (17)	0.0084 (16)	−0.0078 (16)
C12	0.026 (2)	0.027 (2)	0.024 (2)	−0.0164 (18)	0.0064 (17)	−0.0110 (17)
C13	0.035 (3)	0.041 (3)	0.026 (2)	−0.023 (2)	0.0115 (19)	−0.019 (2)
C14	0.058 (4)	0.055 (4)	0.034 (3)	−0.034 (3)	0.010 (3)	−0.026 (3)
C15	0.024 (2)	0.0234 (19)	0.0158 (16)	−0.0157 (17)	0.0046 (14)	−0.0080 (15)
C16	0.0218 (19)	0.0181 (18)	0.0155 (16)	−0.0095 (15)	0.0031 (14)	−0.0072 (14)
C17	0.0188 (19)	0.023 (2)	0.0209 (18)	−0.0061 (16)	0.0003 (15)	−0.0092 (16)
C18	0.022 (2)	0.0176 (18)	0.0221 (19)	−0.0029 (16)	0.0036 (15)	−0.0094 (16)
C19	0.032 (2)	0.0203 (19)	0.0213 (18)	−0.0178 (18)	0.0104 (16)	−0.0103 (16)
C20	0.039 (3)	0.039 (3)	0.026 (2)	−0.024 (2)	0.009 (2)	−0.016 (2)
C21	0.043 (3)	0.033 (3)	0.028 (2)	−0.022 (2)	0.010 (2)	−0.017 (2)
C22	0.037 (3)	0.042 (3)	0.031 (2)	−0.023 (2)	0.012 (2)	−0.024 (2)
P1	0.0183 (5)	0.0159 (4)	0.0173 (4)	−0.0078 (4)	0.0065 (4)	−0.0096 (4)
F1	0.085 (3)	0.0284 (16)	0.0167 (13)	−0.0055 (18)	0.0095 (16)	−0.0087 (12)
F2	0.0351 (18)	0.0304 (16)	0.087 (3)	−0.0241 (15)	0.0275 (18)	−0.0333 (19)
F3	0.068 (2)	0.0251 (15)	0.0168 (12)	−0.0126 (15)	0.0001 (13)	−0.0101 (11)
F4	0.0286 (15)	0.0293 (15)	0.057 (2)	−0.0171 (13)	0.0074 (14)	−0.0260 (15)
F5	0.0254 (15)	0.0274 (14)	0.0473 (18)	−0.0080 (12)	0.0142 (13)	−0.0235 (14)
F6	0.0217 (13)	0.0262 (14)	0.0408 (16)	−0.0056 (11)	0.0103 (12)	−0.0214 (13)

Ag1—C16i	2.073 (4)	C12—C13	1.531 (7)
Ag1—C8	2.089 (4)	C12—H12A	0.9700
N1—C8	1.348 (5)	C12—H12B	0.9700
N1—C9	1.386 (6)	C13—C14	1.514 (7)
N1—C7	1.470 (6)	C13—H13A	0.9700
N2—C8	1.367 (5)	C13—H13B	0.9700
N2—C10	1.379 (5)	C14—H14A	0.9600
N2—C11	1.476 (6)	C14—H14B	0.9600
N3—C16	1.368 (5)	C14—H14C	0.9600
N3—C17	1.379 (6)	C15—H15A	0.9700
N3—C15	1.463 (5)	C15—H15B	0.9700
N4—C16	1.367 (5)	C16—Ag1i	2.073 (4)
N4—C18	1.394 (6)	C17—C18	1.360 (7)
N4—C19	1.470 (6)	C17—H17A	0.9300
C1—C2	1.384 (6)	C18—H18A	0.9300
C1—C6	1.395 (6)	C19—C20	1.530 (7)
C1—H1A	0.9300	C19—H19A	0.9700
C2—C3	1.394 (6)	C19—H19B	0.9700
C2—H2A	0.9300	C20—C21	1.509 (7)
C3—C4	1.392 (6)	C20—H20A	0.9700
C3—C15	1.518 (5)	C20—H20B	0.9700
C4—C5	1.400 (6)	C21—C22	1.516 (7)
C4—H4A	0.9300	C21—H21A	0.9700
C5—C6	1.384 (6)	C21—H21B	0.9700
C5—H5A	0.9300	C22—H22A	0.9600
C6—C7	1.516 (6)	C22—H22B	0.9600
C7—H7A	0.9700	C22—H22C	0.9600
C7—H7B	0.9700	P1—F5	1.588 (3)
C9—C10	1.359 (7)	P1—F3	1.590 (3)
C9—H9A	0.9300	P1—F2	1.594 (3)
C10—H10A	0.9300	P1—F1	1.606 (3)
C11—C12	1.518 (6)	P1—F6	1.606 (3)
C11—H11A	0.9700	P1—F4	1.613 (3)
C11—H11B	0.9700
C16i—Ag1—C8	179.40 (15)	C12—C13—H13B	109.3
C8—N1—C9	111.3 (4)	H13A—C13—H13B	107.9
C8—N1—C7	124.8 (4)	C13—C14—H14A	109.5
C9—N1—C7	123.7 (4)	C13—C14—H14B	109.5
C8—N2—C10	111.7 (4)	H14A—C14—H14B	109.5
C8—N2—C11	125.2 (4)	C13—C14—H14C	109.5
C10—N2—C11	123.1 (4)	H14A—C14—H14C	109.5
C16—N3—C17	111.9 (4)	H14B—C14—H14C	109.5
C16—N3—C15	123.6 (4)	N3—C15—C3	113.3 (3)
C17—N3—C15	124.5 (4)	N3—C15—H15A	108.9
C16—N4—C18	111.5 (4)	C3—C15—H15A	108.9
C16—N4—C19	124.8 (4)	N3—C15—H15B	108.9
C18—N4—C19	123.6 (4)	C3—C15—H15B	108.9
C2—C1—C6	121.1 (4)	H15A—C15—H15B	107.7
C2—C1—H1A	119.4	N4—C16—N3	103.5 (4)
C6—C1—H1A	119.4	N4—C16—Ag1i	128.5 (3)
C1—C2—C3	120.6 (4)	N3—C16—Ag1i	127.8 (3)
C1—C2—H2A	119.7	C18—C17—N3	106.8 (4)
C3—C2—H2A	119.7	C18—C17—H17A	126.6
C4—C3—C2	118.5 (4)	N3—C17—H17A	126.6
C4—C3—C15	122.5 (4)	C17—C18—N4	106.2 (4)
C2—C3—C15	119.0 (4)	C17—C18—H18A	126.9
C3—C4—C5	120.6 (4)	N4—C18—H18A	126.9
C3—C4—H4A	119.7	N4—C19—C20	112.2 (4)
C5—C4—H4A	119.7	N4—C19—H19A	109.2
C6—C5—C4	120.7 (4)	C20—C19—H19A	109.2
C6—C5—H5A	119.6	N4—C19—H19B	109.2
C4—C5—H5A	119.6	C20—C19—H19B	109.2
C5—C6—C1	118.4 (4)	H19A—C19—H19B	107.9
C5—C6—C7	121.5 (4)	C21—C20—C19	115.9 (4)
C1—C6—C7	120.1 (4)	C21—C20—H20A	108.3
N1—C7—C6	110.8 (3)	C19—C20—H20A	108.3
N1—C7—H7A	109.5	C21—C20—H20B	108.3
C6—C7—H7A	109.5	C19—C20—H20B	108.3
N1—C7—H7B	109.5	H20A—C20—H20B	107.4
C6—C7—H7B	109.5	C20—C21—C22	112.4 (5)
H7A—C7—H7B	108.1	C20—C21—H21A	109.1
N1—C8—N2	104.1 (3)	C22—C21—H21A	109.1
N1—C8—Ag1	130.4 (3)	C20—C21—H21B	109.1
N2—C8—Ag1	125.4 (3)	C22—C21—H21B	109.1
C10—C9—N1	107.0 (4)	H21A—C21—H21B	107.9
C10—C9—H9A	126.5	C21—C22—H22A	109.5
N1—C9—H9A	126.5	C21—C22—H22B	109.5
C9—C10—N2	105.9 (4)	H22A—C22—H22B	109.5
C9—C10—H10A	127.1	C21—C22—H22C	109.5
N2—C10—H10A	127.1	H22A—C22—H22C	109.5
N2—C11—C12	112.6 (4)	H22B—C22—H22C	109.5
N2—C11—H11A	109.1	F5—P1—F3	90.87 (19)
C12—C11—H11A	109.1	F5—P1—F2	91.02 (18)
N2—C11—H11B	109.1	F3—P1—F2	90.1 (2)
C12—C11—H11B	109.1	F5—P1—F1	90.93 (19)
H11A—C11—H11B	107.8	F3—P1—F1	177.6 (2)
C11—C12—C13	114.1 (4)	F2—P1—F1	91.5 (2)
C11—C12—H12A	108.7	F5—P1—F6	179.20 (18)
C13—C12—H12A	108.7	F3—P1—F6	89.93 (18)
C11—C12—H12B	108.7	F2—P1—F6	89.00 (17)
C13—C12—H12B	108.7	F1—P1—F6	88.27 (19)
H12A—C12—H12B	107.6	F5—P1—F4	89.49 (17)
C14—C13—C12	111.8 (5)	F3—P1—F4	89.6 (2)
C14—C13—H13A	109.3	F2—P1—F4	179.4 (2)
C12—C13—H13A	109.3	F1—P1—F4	88.8 (2)
C14—C13—H13B	109.3	F6—P1—F4	90.49 (17)
C6—C1—C2—C3	1.0 (8)	C11—N2—C10—C9	−177.9 (4)
C1—C2—C3—C4	−1.0 (7)	C8—N2—C11—C12	−101.3 (5)
C1—C2—C3—C15	179.8 (4)	C10—N2—C11—C12	76.3 (5)
C2—C3—C4—C5	0.2 (7)	N2—C11—C12—C13	63.3 (5)
C15—C3—C4—C5	179.3 (4)	C11—C12—C13—C14	175.3 (5)
C3—C4—C5—C6	0.7 (7)	C16—N3—C15—C3	85.2 (5)
C4—C5—C6—C1	−0.8 (7)	C17—N3—C15—C3	−92.3 (5)
C4—C5—C6—C7	178.5 (4)	C4—C3—C15—N3	34.6 (6)
C2—C1—C6—C5	−0.1 (7)	C2—C3—C15—N3	−146.2 (4)
C2—C1—C6—C7	−179.3 (5)	C18—N4—C16—N3	−1.5 (4)
C8—N1—C7—C6	103.8 (4)	C19—N4—C16—N3	175.3 (3)
C9—N1—C7—C6	−69.9 (5)	C18—N4—C16—Ag1i	173.8 (3)
C5—C6—C7—N1	109.1 (5)	C19—N4—C16—Ag1i	−9.4 (6)
C1—C6—C7—N1	−71.7 (5)	C17—N3—C16—N4	1.1 (4)
C9—N1—C8—N2	−0.4 (4)	C15—N3—C16—N4	−176.7 (3)
C7—N1—C8—N2	−174.9 (3)	C17—N3—C16—Ag1i	−174.3 (3)
C9—N1—C8—Ag1	176.5 (3)	C15—N3—C16—Ag1i	8.0 (6)
C7—N1—C8—Ag1	2.0 (6)	C16—N3—C17—C18	−0.3 (5)
C10—N2—C8—N1	0.2 (4)	C15—N3—C17—C18	177.4 (4)
C11—N2—C8—N1	178.1 (4)	N3—C17—C18—N4	−0.6 (5)
C10—N2—C8—Ag1	−176.8 (3)	C16—N4—C18—C17	1.4 (5)
C11—N2—C8—Ag1	1.0 (5)	C19—N4—C18—C17	−175.4 (4)
C8—N1—C9—C10	0.5 (5)	C16—N4—C19—C20	−122.3 (5)
C7—N1—C9—C10	175.0 (4)	C18—N4—C19—C20	54.0 (6)
N1—C9—C10—N2	−0.3 (5)	N4—C19—C20—C21	58.0 (6)
C8—N2—C10—C9	0.0 (5)	C19—C20—C21—C22	−167.5 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···F3i	0.93	2.42	3.251 (6)	149
C5—H5A···F1ii	0.93	2.52	3.392 (6)	157
C7—H7B···F5ii	0.97	2.44	3.367 (6)	160
C11—H11A···F6iii	0.97	2.44	3.364 (7)	159
C11—H11B···F2iv	0.97	2.38	3.129 (7)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯F3i	0.93	2.42	3.251 (6)	149
C5—H5A⋯F1ii	0.93	2.52	3.392 (6)	157
C7—H7B⋯F5ii	0.97	2.44	3.367 (6)	160
C11—H11A⋯F6iii	0.97	2.44	3.364 (7)	159
C11—H11B⋯F2iv	0.97	2.38	3.129 (7)	134

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