(2,2'-Bipyridine-κN,N')bromido(1,4,7-trithia-cyclo-nonane-κS,S',S'')ruthenium(II) hexa-fluoridophosphate.

The title compound, [RuBr(C(10)H(8)N(2))(C(6)H(12)S(3))]PF(6) or [RuBr(bpy)([9]aneS(3))]PF(6) ([9]aneS(3) is 1,4,7-trithia-cyclo-nonane and bpy is 2,2'-bipyridine), exhibits a very similar octahedral coordination geometry for the Ru(2+) atom to that of its [RuCl(bpy)([9]aneS(3))](+) analogue, with only the chloride ligand being substituted by a bromide ligand. The presence of a PF(6) (-) anion (alongside with the coordinated bromide ligand) promotes the existence of an extensive network of weak C-H⋯X (X = F, Br) inter-actions.

Related literature

For general background to the cytotoxic activity of compounds with the {Ru[9]aneS3} moiety, see: Bratsos et al. (2008 ▶); Serli et al. (2005 ▶). For isotypic compounds based on the [RuCl(bpy)([9]aneS3)]+ cation, see: Serli et al. (2005 ▶); Goodfellow et al. (1997 ▶); Fernandes et al. (2010 ▶). For previous work from our research group on the use of related compounds, see: Marques, Braga et al. (2009 ▶); Marques, Santos et al. (2009 ▶).

Experimental

Crystal data

[RuBr(C10H8N2)(C6H12S3)]PF6

M = 662.47

Monoclinic,

a = 12.0660 (7) Å

b = 13.4377 (8) Å

c = 13.3359 (8) Å

β = 98.446 (3)°

V = 2138.8 (2) Å3

Z = 4

Mo Kα radiation

μ = 3.03 mm−1

T = 150 K

0.16 × 0.12 × 0.10 mm

Data collection

Bruker APEXII X8 KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ▶) T min = 0.643, T max = 0.752

38626 measured reflections

5736 independent reflections

4989 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.022

wR(F 2) = 0.046

S = 1.06

5736 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.63 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT-Plus (Bruker, 2005 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811002662/cv5041sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811002662/cv5041Isup2.hkl

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

[RuBr(C10H8N2)(C6H12S3)]PF6	F(000) = 1304
Mr = 662.47	Dx = 2.057 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9897 reflections
a = 12.0660 (7) Å	θ = 2.6–30.4°
b = 13.4377 (8) Å	µ = 3.03 mm−1
c = 13.3359 (8) Å	T = 150 K
β = 98.446 (3)°	Block, orange
V = 2138.8 (2) Å3	0.16 × 0.12 × 0.10 mm
Z = 4

Bruker APEXII X8 KappaCCD diffractometer	5736 independent reflections
Radiation source: fine-focus sealed tube	4989 reflections with I > 2σ(I)
graphite	Rint = 0.035
ω and φ scans	θmax = 29.1°, θmin = 3.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −16→13
Tmin = 0.643, Tmax = 0.752	k = −14→18
38626 measured reflections	l = −18→15

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)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.046	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0166P)2 + 1.1306P] where P = (Fo2 + 2Fc2)/3
5736 reflections	(Δ/σ)max = 0.002
271 parameters	Δρmax = 0.52 e Å−3
0 restraints	Δρmin = −0.63 e Å−3

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.

	x	y	z	Uiso*/Ueq
Ru1	0.833904 (11)	0.100271 (10)	0.308671 (10)	0.01013 (4)
Br1	0.971376 (14)	0.213830 (13)	0.421622 (13)	0.01640 (5)
S1	0.71000 (3)	0.00388 (3)	0.20501 (3)	0.01421 (9)
S2	0.88870 (4)	0.17069 (3)	0.16651 (3)	0.01378 (9)
S3	0.96835 (3)	−0.02031 (3)	0.29973 (3)	0.01433 (9)
N1	0.77196 (11)	0.04462 (11)	0.43571 (10)	0.0125 (3)
N2	0.71002 (12)	0.20371 (11)	0.32732 (10)	0.0126 (3)
C1	0.81031 (15)	−0.03531 (14)	0.49059 (13)	0.0173 (4)
H1	0.8766	−0.0668	0.4760	0.021*
C2	0.75773 (16)	−0.07386 (15)	0.56726 (14)	0.0197 (4)
H2	0.7866	−0.1313	0.6035	0.024*
C3	0.66248 (16)	−0.02759 (14)	0.59036 (14)	0.0195 (4)
H3	0.6240	−0.0534	0.6419	0.023*
C4	0.62398 (15)	0.05704 (14)	0.53721 (13)	0.0182 (4)
H4	0.5599	0.0911	0.5534	0.022*
C5	0.67964 (14)	0.09190 (13)	0.46003 (13)	0.0135 (3)
C6	0.64656 (14)	0.18211 (13)	0.40071 (13)	0.0128 (3)
C7	0.55971 (14)	0.24479 (14)	0.41964 (13)	0.0165 (4)
H7	0.5145	0.2275	0.4696	0.020*
C8	0.53990 (15)	0.33168 (14)	0.36549 (14)	0.0191 (4)
H8	0.4811	0.3750	0.3777	0.023*
C9	0.60684 (15)	0.35527 (14)	0.29292 (14)	0.0186 (4)
H9	0.5958	0.4156	0.2556	0.022*
C10	0.68995 (15)	0.28951 (14)	0.27577 (13)	0.0169 (4)
H10	0.7350	0.3055	0.2253	0.020*
C11	0.69306 (15)	0.07354 (14)	0.08615 (13)	0.0177 (4)
H11A	0.6553	0.0307	0.0311	0.021*
H11B	0.6441	0.1317	0.0922	0.021*
C12	0.80353 (15)	0.10941 (14)	0.05783 (13)	0.0176 (4)
H12A	0.7890	0.1569	0.0006	0.021*
H12B	0.8454	0.0521	0.0355	0.021*
C13	1.02665 (15)	0.11727 (14)	0.16039 (15)	0.0185 (4)
H13A	1.0454	0.1271	0.0913	0.022*
H13B	1.0831	0.1534	0.2083	0.022*
C14	1.03368 (15)	0.00714 (14)	0.18570 (14)	0.0188 (4)
H14A	1.1132	−0.0137	0.1976	0.023*
H14B	0.9952	−0.0315	0.1275	0.023*
C15	0.88524 (15)	−0.12899 (13)	0.25441 (14)	0.0168 (4)
H15A	0.9348	−0.1787	0.2289	0.020*
H15B	0.8544	−0.1593	0.3120	0.020*
C16	0.78971 (15)	−0.10518 (13)	0.17114 (14)	0.0180 (4)
H16A	0.7391	−0.1633	0.1596	0.022*
H16B	0.8199	−0.0915	0.1074	0.022*
P1	0.34992 (4)	0.16856 (4)	0.13197 (4)	0.01782 (10)
F1	0.39585 (10)	0.13350 (10)	0.03098 (9)	0.0359 (3)
F2	0.41610 (11)	0.27096 (10)	0.12942 (10)	0.0384 (3)
F3	0.45640 (10)	0.11898 (10)	0.19885 (10)	0.0372 (3)
F4	0.28321 (10)	0.06540 (9)	0.13318 (10)	0.0327 (3)
F5	0.24266 (10)	0.21698 (10)	0.06555 (10)	0.0367 (3)
F6	0.30399 (11)	0.20190 (9)	0.23321 (9)	0.0343 (3)

	U11	U22	U33	U12	U13	U23
Ru1	0.01007 (7)	0.00943 (7)	0.01135 (7)	0.00047 (5)	0.00314 (5)	−0.00005 (5)
Br1	0.01564 (9)	0.01541 (10)	0.01780 (9)	−0.00099 (7)	0.00133 (7)	−0.00329 (7)
S1	0.0131 (2)	0.0135 (2)	0.0161 (2)	−0.00181 (17)	0.00253 (16)	0.00033 (17)
S2	0.0153 (2)	0.0123 (2)	0.0147 (2)	−0.00110 (17)	0.00545 (16)	0.00033 (17)
S3	0.0128 (2)	0.0124 (2)	0.0185 (2)	0.00123 (17)	0.00418 (16)	0.00010 (18)
N1	0.0130 (7)	0.0127 (8)	0.0120 (7)	0.0009 (6)	0.0023 (5)	−0.0006 (6)
N2	0.0132 (7)	0.0121 (8)	0.0123 (7)	0.0007 (6)	0.0017 (5)	−0.0012 (6)
C1	0.0190 (9)	0.0166 (10)	0.0163 (9)	0.0032 (8)	0.0022 (7)	0.0006 (7)
C2	0.0264 (10)	0.0165 (10)	0.0160 (9)	0.0005 (8)	0.0027 (7)	0.0036 (8)
C3	0.0252 (10)	0.0192 (10)	0.0155 (9)	−0.0027 (8)	0.0073 (7)	0.0021 (8)
C4	0.0184 (9)	0.0188 (10)	0.0183 (9)	0.0003 (8)	0.0061 (7)	−0.0009 (8)
C5	0.0141 (8)	0.0131 (9)	0.0130 (8)	−0.0011 (7)	0.0013 (6)	−0.0028 (7)
C6	0.0118 (8)	0.0142 (9)	0.0122 (8)	−0.0008 (7)	0.0008 (6)	−0.0019 (7)
C7	0.0138 (8)	0.0198 (10)	0.0167 (9)	0.0007 (7)	0.0047 (7)	−0.0016 (8)
C8	0.0175 (9)	0.0193 (10)	0.0202 (9)	0.0074 (8)	0.0021 (7)	−0.0022 (8)
C9	0.0234 (9)	0.0144 (9)	0.0174 (9)	0.0047 (8)	0.0013 (7)	0.0020 (7)
C10	0.0186 (9)	0.0169 (10)	0.0160 (9)	0.0014 (7)	0.0051 (7)	0.0012 (7)
C11	0.0187 (9)	0.0181 (10)	0.0154 (9)	−0.0013 (8)	−0.0011 (7)	0.0017 (8)
C12	0.0206 (9)	0.0185 (10)	0.0137 (9)	−0.0014 (8)	0.0026 (7)	−0.0004 (7)
C13	0.0152 (8)	0.0183 (10)	0.0239 (10)	−0.0026 (8)	0.0093 (7)	−0.0004 (8)
C14	0.0174 (9)	0.0177 (10)	0.0237 (10)	0.0007 (8)	0.0108 (7)	−0.0011 (8)
C15	0.0207 (9)	0.0094 (9)	0.0214 (9)	0.0014 (7)	0.0067 (7)	0.0001 (7)
C16	0.0217 (9)	0.0110 (9)	0.0215 (10)	−0.0013 (7)	0.0036 (7)	−0.0031 (7)
P1	0.0179 (2)	0.0200 (3)	0.0164 (2)	−0.0014 (2)	0.00541 (18)	0.0004 (2)
F1	0.0393 (7)	0.0464 (8)	0.0265 (7)	−0.0168 (6)	0.0197 (5)	−0.0138 (6)
F2	0.0476 (8)	0.0305 (7)	0.0366 (7)	−0.0212 (6)	0.0052 (6)	−0.0047 (6)
F3	0.0240 (6)	0.0488 (8)	0.0377 (7)	0.0119 (6)	0.0007 (5)	0.0029 (6)
F4	0.0318 (7)	0.0226 (6)	0.0474 (8)	−0.0071 (5)	0.0185 (6)	0.0020 (6)
F5	0.0310 (7)	0.0393 (8)	0.0368 (7)	0.0034 (6)	−0.0051 (6)	0.0124 (6)
F6	0.0441 (7)	0.0375 (8)	0.0246 (6)	0.0123 (6)	0.0157 (6)	−0.0023 (6)

Ru1—N1	2.0881 (14)	C7—H7	0.9500
Ru1—N2	2.0826 (14)	C8—C9	1.385 (3)
Ru1—S1	2.2840 (5)	C8—H8	0.9500
Ru1—S2	2.3011 (4)	C9—C10	1.381 (3)
Ru1—S3	2.3083 (5)	C9—H9	0.9500
Ru1—Br1	2.5720 (2)	C10—H10	0.9500
S1—C11	1.8264 (18)	C11—C12	1.516 (2)
S1—C16	1.8451 (18)	C11—H11A	0.9900
S2—C13	1.8255 (18)	C11—H11B	0.9900
S2—C12	1.8432 (18)	C12—H12A	0.9900
S3—C15	1.8236 (19)	C12—H12B	0.9900
S3—C14	1.8499 (17)	C13—C14	1.517 (3)
N1—C1	1.343 (2)	C13—H13A	0.9900
N1—C5	1.362 (2)	C13—H13B	0.9900
N2—C10	1.346 (2)	C14—H14A	0.9900
N2—C6	1.360 (2)	C14—H14B	0.9900
C1—C2	1.381 (2)	C15—C16	1.513 (3)
C1—H1	0.9500	C15—H15A	0.9900
C2—C3	1.381 (3)	C15—H15B	0.9900
C2—H2	0.9500	C16—H16A	0.9900
C3—C4	1.384 (3)	C16—H16B	0.9900
C3—H3	0.9500	P1—F2	1.5938 (13)
C4—C5	1.390 (2)	P1—F5	1.5956 (13)
C4—H4	0.9500	P1—F6	1.5970 (12)
C5—C6	1.470 (2)	P1—F3	1.5980 (13)
C6—C7	1.396 (2)	P1—F1	1.6007 (12)
C7—C8	1.375 (3)	P1—F4	1.6043 (12)
N2—Ru1—N1	78.08 (5)	C8—C9—H9	120.6
N2—Ru1—S1	91.91 (4)	N2—C10—C9	122.97 (16)
N1—Ru1—S1	90.43 (4)	N2—C10—H10	118.5
N2—Ru1—S2	97.01 (4)	C9—C10—H10	118.5
S1—Ru1—S2	88.644 (16)	C12—C11—S1	112.87 (13)
N1—Ru1—S3	97.38 (4)	C12—C11—H11A	109.0
S1—Ru1—S3	88.460 (17)	S1—C11—H11A	109.0
S2—Ru1—S3	87.533 (16)	C12—C11—H11B	109.0
N2—Ru1—Br1	86.93 (4)	S1—C11—H11B	109.0
N1—Ru1—Br1	90.81 (4)	H11A—C11—H11B	107.8
S2—Ru1—Br1	89.993 (13)	C11—C12—S2	110.80 (12)
S3—Ru1—Br1	92.811 (13)	C11—C12—H12A	109.5
N1—Ru1—S2	174.97 (4)	S2—C12—H12A	109.5
N2—Ru1—S3	175.45 (4)	C11—C12—H12B	109.5
S1—Ru1—Br1	178.095 (13)	S2—C12—H12B	109.5
C11—S1—C16	100.98 (9)	H12A—C12—H12B	108.1
C11—S1—Ru1	102.38 (6)	C14—C13—S2	113.27 (12)
C16—S1—Ru1	106.28 (6)	C14—C13—H13A	108.9
C13—S2—C12	101.30 (9)	S2—C13—H13A	108.9
C13—S2—Ru1	104.44 (6)	C14—C13—H13B	108.9
C12—S2—Ru1	105.64 (6)	S2—C13—H13B	108.9
C15—S3—C14	99.63 (8)	H13A—C13—H13B	107.7
C15—S3—Ru1	102.88 (6)	C13—C14—S3	111.14 (12)
C14—S3—Ru1	106.86 (6)	C13—C14—H14A	109.4
C1—N1—C5	118.13 (14)	S3—C14—H14A	109.4
C1—N1—Ru1	126.36 (11)	C13—C14—H14B	109.4
C5—N1—Ru1	115.39 (11)	S3—C14—H14B	109.4
C10—N2—C6	118.19 (15)	H14A—C14—H14B	108.0
C10—N2—Ru1	126.09 (11)	C16—C15—S3	113.37 (13)
C6—N2—Ru1	115.69 (11)	C16—C15—H15A	108.9
N1—C1—C2	122.99 (17)	S3—C15—H15A	108.9
N1—C1—H1	118.5	C16—C15—H15B	108.9
C2—C1—H1	118.5	S3—C15—H15B	108.9
C3—C2—C1	118.96 (18)	H15A—C15—H15B	107.7
C3—C2—H2	120.5	C15—C16—S1	110.89 (12)
C1—C2—H2	120.5	C15—C16—H16A	109.5
C2—C3—C4	118.92 (16)	S1—C16—H16A	109.5
C2—C3—H3	120.5	C15—C16—H16B	109.5
C4—C3—H3	120.5	S1—C16—H16B	109.5
C3—C4—C5	119.58 (17)	H16A—C16—H16B	108.0
C3—C4—H4	120.2	F2—P1—F5	90.24 (7)
C5—C4—H4	120.2	F2—P1—F6	90.75 (7)
N1—C5—C4	121.33 (16)	F5—P1—F6	90.06 (7)
N1—C5—C6	115.04 (14)	F2—P1—F3	90.43 (8)
C4—C5—C6	123.61 (16)	F5—P1—F3	179.30 (8)
N2—C6—C7	121.23 (16)	F6—P1—F3	89.74 (7)
N2—C6—C5	115.22 (14)	F2—P1—F1	89.98 (7)
C7—C6—C5	123.49 (15)	F5—P1—F1	90.33 (7)
C8—C7—C6	119.64 (16)	F6—P1—F1	179.17 (8)
C8—C7—H7	120.2	F3—P1—F1	89.86 (7)
C6—C7—H7	120.2	F2—P1—F4	179.36 (7)
C7—C8—C9	119.13 (17)	F5—P1—F4	89.46 (7)
C7—C8—H8	120.4	F6—P1—F4	89.83 (7)
C9—C8—H8	120.4	F3—P1—F4	89.86 (7)
C10—C9—C8	118.78 (17)	F1—P1—F4	89.45 (7)
C10—C9—H9	120.6
N2—Ru1—S1—C11	75.99 (7)	Ru1—N1—C1—C2	−173.00 (14)
N1—Ru1—S1—C11	154.07 (7)	N1—C1—C2—C3	−1.2 (3)
S2—Ru1—S1—C11	−20.99 (6)	C1—C2—C3—C4	−1.2 (3)
S3—Ru1—S1—C11	−108.55 (6)	C2—C3—C4—C5	1.9 (3)
N2—Ru1—S1—C16	−178.51 (7)	C1—N1—C5—C4	−2.1 (2)
N1—Ru1—S1—C16	−100.42 (7)	Ru1—N1—C5—C4	174.23 (13)
S2—Ru1—S1—C16	84.52 (6)	C1—N1—C5—C6	176.53 (15)
S3—Ru1—S1—C16	−3.05 (6)	Ru1—N1—C5—C6	−7.18 (19)
N2—Ru1—S2—C13	161.69 (8)	C3—C4—C5—N1	−0.3 (3)
S1—Ru1—S2—C13	−106.56 (7)	C3—C4—C5—C6	−178.74 (17)
S3—Ru1—S2—C13	−18.04 (7)	C10—N2—C6—C7	2.6 (2)
Br1—Ru1—S2—C13	74.78 (6)	Ru1—N2—C6—C7	−179.04 (13)
N2—Ru1—S2—C12	−91.93 (7)	C10—N2—C6—C5	−174.73 (15)
S1—Ru1—S2—C12	−0.17 (6)	Ru1—N2—C6—C5	3.59 (19)
S3—Ru1—S2—C12	88.35 (6)	N1—C5—C6—N2	2.4 (2)
Br1—Ru1—S2—C12	−178.84 (6)	C4—C5—C6—N2	−179.06 (16)
N1—Ru1—S3—C15	72.45 (7)	N1—C5—C6—C7	−174.92 (16)
S1—Ru1—S3—C15	−17.78 (6)	C4—C5—C6—C7	3.6 (3)
S2—Ru1—S3—C15	−106.49 (6)	N2—C6—C7—C8	−2.1 (3)
Br1—Ru1—S3—C15	163.64 (6)	C5—C6—C7—C8	175.04 (17)
N1—Ru1—S3—C14	176.84 (8)	C6—C7—C8—C9	0.0 (3)
S1—Ru1—S3—C14	86.61 (7)	C7—C8—C9—C10	1.4 (3)
S2—Ru1—S3—C14	−2.10 (7)	C6—N2—C10—C9	−1.2 (3)
Br1—Ru1—S3—C14	−91.97 (7)	Ru1—N2—C10—C9	−179.30 (14)
N2—Ru1—N1—C1	−177.12 (15)	C8—C9—C10—N2	−0.8 (3)
S1—Ru1—N1—C1	91.02 (14)	C16—S1—C11—C12	−64.36 (15)
S3—Ru1—N1—C1	2.51 (15)	Ru1—S1—C11—C12	45.21 (14)
Br1—Ru1—N1—C1	−90.43 (14)	S1—C11—C12—S2	−48.58 (17)
N2—Ru1—N1—C5	6.94 (12)	C13—S2—C12—C11	135.80 (13)
S1—Ru1—N1—C5	−84.92 (12)	Ru1—S2—C12—C11	27.14 (14)
S3—Ru1—N1—C5	−173.42 (11)	C12—S2—C13—C14	−68.39 (15)
Br1—Ru1—N1—C5	93.64 (12)	Ru1—S2—C13—C14	41.20 (15)
N1—Ru1—N2—C10	172.54 (15)	S2—C13—C14—S3	−45.34 (17)
S1—Ru1—N2—C10	−97.42 (14)	C15—S3—C14—C13	133.84 (14)
S2—Ru1—N2—C10	−8.56 (15)	Ru1—S3—C14—C13	27.13 (15)
Br1—Ru1—N2—C10	81.06 (14)	C14—S3—C15—C16	−67.85 (14)
N1—Ru1—N2—C6	−5.62 (12)	Ru1—S3—C15—C16	42.06 (13)
S1—Ru1—N2—C6	84.42 (12)	S3—C15—C16—S1	−47.66 (15)
S2—Ru1—N2—C6	173.28 (11)	C11—S1—C16—C15	135.46 (13)
Br1—Ru1—N2—C6	−97.10 (12)	Ru1—S1—C16—C15	28.95 (13)
C5—N1—C1—C2	2.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Br1i	0.95	2.90	3.6274 (19)	135
C8—H8···F1ii	0.95	2.42	3.039 (2)	122
C11—H11A···F1iii	0.99	2.41	3.292 (2)	149
C15—H15A···Br1iv	0.99	2.84	3.7627 (18)	156
C16—H16A···F6v	0.99	2.41	3.170 (2)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯Br1i	0.95	2.90	3.6274 (19)	135
C8—H8⋯F1ii	0.95	2.42	3.039 (2)	122
C11—H11A⋯F1iii	0.99	2.41	3.292 (2)	149
C15—H15A⋯Br1iv	0.99	2.84	3.7627 (18)	156
C16—H16A⋯F6v	0.99	2.41	3.170 (2)	133

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