Synthesis and structures of photoactive rhenium carbonyl complexes derived from 2-(pyridin-2-yl)-1,3-benzo­thia­zole, 2-(quinolin-2-yl)-1,3-benzo­thiazole and 1,10-phenanthroline

Carbon monoxide (CO) has recently been identified as a gaseous signaling mol­ecule that exerts various salutary effects in mammalian pathophysiology. Photoactive metal carbonyl complexes (photoCORMs) are ideal exogenous candidates for more controllable and site-specific CO delivery compared to gaseous CO. Along this line, our group has been engaged for the past few years in developing group-7-based photoCORMs towards the efficient eradication of various malignant cells. Moreover, several such complexes can be tracked within cancerous cells by virtue of their luminescence. The inherent luminecscent nature of some photoCORMs and the change in emission wavelength upon CO release also provide a covenient means to track the entry of the prodrug and, in some cases, both the entry and CO release from the prodrug. In continuation of the research circumscribing the development of trackable photoCORMs and also to graft such mol­ecules covalently to conventional delivery vehicles, we report herein the synthesis and structures of three rhenium carbonyl complexes, namely, fac-tricarbon­yl[2-(pyridin-2-yl)-1,3-benzo­thia­zole-κ²N,N′](4-vinyl­pyri­dine-κN)rhenium(I) tri­fluoro­methane­sulfonate, [Re(C₇H₇N)(C₁₂H₈N₂S)(CO)₃](CF₃SO₃), (1), fac-tricarbon­yl[2-(quinolin-2-yl)-1,3-benzo­thia­zole-κ²N,N′](4-vinyl­pyridine-κN)rhenium(I) tri­fluoro­methane­sulfonate, [Re(C₇H₇N)(C₁₆H₁₀N₂S)(CO)₃](CF₃SO₃), (2), and fac-tricarbon­yl[1,10-phenanthroline-κ²N,N′](4-vinyl­pyridine-κN)rhenium(I) tri­fluoro­methane­sulfonate, [Re(C₇H₇N)(C₁₂H₈N₂)(CO)₃](CF₃SO₃), (3). In all three complexes, the Re^I center resides in a distorted octa­hedral coordination environment. These complexes exhibit CO release upon exposure to low-power UV light. The apparent CO release rates of the complexes have been measured to assess their comparative CO-donating capacity. The three complexes are highly luminescent and this in turn provides a convenient way to track the entry of the prodrug mol­ecules within biological targets.

Computing details

For all structures, data collection: APEX (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009) and publCIF (Westrip, 2010).

fac-Tricarbonyl[2-(pyridin-2-yl)-1,3-benzothiazole-κ²N,N'](4-vinylpyridine-κN)rhenium(I) trifluoromethanesulfonate (1)

Crystal data

[Re(C7H7N)(C12H8N2S)(CO)3](CF3SO3)·CH2Cl2	Z = 2
Mr = 821.62	F(000) = 796
Triclinic, P1	Dx = 1.928 Mg m^−3
a = 8.596 Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.217 Å	Cell parameters from 9893 reflections
c = 15.161 Å	θ = 2.2–28.9°
α = 92.88°	µ = 4.70 mm^−1
β = 104.12°	T = 293 K
γ = 91.19°	Yellow, block
V = 1415.1 Å^3	0.20 × 0.18 × 0.15 mm

Data collection

Bruker APEXII diffractometer	5706 independent reflections
Radiation source: fine-focus sealed tube	5462 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
Detector resolution: 8.33 pixels mm^-1	θmax = 26.4°, θmin = 2.2°
ω–scans	h = −10→10
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −14→14
Tmin = 0.635, Tmax = 0.746	l = −18→18
13569 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.020	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.051	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.028P)^2 + 1.0417P] where P = (Fo^2 + 2Fc^2)/3
5706 reflections	(Δ/σ)max = 0.003
370 parameters	Δρmax = 0.91 e Å^−3
0 restraints	Δρmin = −0.73 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Re1	0.37292 (2)	0.17999 (2)	0.65195 (2)	0.03390 (5)
S1	0.91621 (9)	0.27277 (8)	0.75416 (6)	0.04765 (18)
S2	0.22083 (10)	0.78971 (7)	0.88275 (6)	0.04771 (18)
Cl1	0.74059 (15)	0.33457 (11)	0.33575 (8)	0.0802 (3)
Cl2	0.7749 (3)	0.19678 (14)	0.49609 (10)	0.1200 (6)
N2	0.6108 (3)	0.2687 (2)	0.68311 (16)	0.0345 (5)
N1	0.5393 (3)	0.0481 (2)	0.71952 (16)	0.0355 (5)
N3	0.3615 (3)	0.2478 (2)	0.78933 (17)	0.0375 (5)
O3	0.0641 (3)	0.0274 (2)	0.6296 (2)	0.0664 (7)
O2	0.1593 (3)	0.3798 (2)	0.5672 (2)	0.0696 (8)
O1	0.3678 (4)	0.0924 (3)	0.45629 (18)	0.0756 (8)
F3	0.2736 (4)	0.7717 (3)	1.05892 (17)	0.1007 (9)
O4	0.0894 (4)	0.7052 (3)	0.8681 (2)	0.0722 (8)
C9	0.7293 (3)	0.2031 (3)	0.72362 (18)	0.0360 (6)
C8	0.6983 (3)	0.0808 (3)	0.74174 (18)	0.0359 (6)
O5	0.3729 (4)	0.7382 (3)	0.8888 (2)	0.0835 (9)
O6	0.1888 (4)	0.8922 (3)	0.8294 (2)	0.0755 (8)
C15	0.6678 (4)	0.3837 (3)	0.6717 (2)	0.0382 (6)
F2	0.3448 (4)	0.9374 (3)	1.0232 (2)	0.1087 (11)
F1	0.0976 (4)	0.8966 (4)	1.0041 (2)	0.1292 (14)
C3	0.1794 (4)	0.0841 (3)	0.6381 (2)	0.0448 (7)
C2	0.2411 (4)	0.3045 (3)	0.5991 (2)	0.0458 (7)
C10	0.8327 (4)	0.4019 (3)	0.7080 (2)	0.0416 (6)
C7	0.8156 (4)	0.0027 (3)	0.7783 (2)	0.0449 (7)
H7	0.923386	0.026868	0.791705	0.054*
C4	0.4982 (4)	−0.0625 (3)	0.7373 (2)	0.0439 (7)
H4	0.390124	−0.085779	0.723494	0.053*
C5	0.6111 (4)	−0.1431 (3)	0.7755 (2)	0.0502 (8)
H5	0.578560	−0.218616	0.788168	0.060*
C14	0.5785 (4)	0.4756 (3)	0.6304 (3)	0.0512 (8)
H14	0.468783	0.464773	0.605168	0.061*
C1	0.3755 (4)	0.1233 (3)	0.5305 (2)	0.0482 (7)
C20	0.3243 (4)	0.1756 (3)	0.8500 (2)	0.0448 (7)
H20	0.323396	0.093476	0.837932	0.054*
C6	0.7717 (4)	−0.1113 (3)	0.7948 (2)	0.0500 (8)
H6	0.849058	−0.165633	0.818554	0.060*
C12	0.8187 (5)	0.6011 (3)	0.6659 (3)	0.0612 (9)
H12	0.867195	0.675582	0.664333	0.073*
C18	0.2872 (4)	0.3379 (3)	0.9504 (2)	0.0536 (8)
C17	0.3301 (5)	0.4135 (3)	0.8890 (3)	0.0584 (9)
H17	0.333762	0.495886	0.900443	0.070*
C19	0.2876 (4)	0.2176 (3)	0.9289 (2)	0.0524 (8)
H19	0.262615	0.163612	0.968407	0.063*
C16	0.3666 (4)	0.3658 (3)	0.8118 (2)	0.0493 (8)
H16	0.396748	0.417858	0.772587	0.059*
C13	0.6557 (5)	0.5841 (3)	0.6276 (3)	0.0592 (9)
H13	0.597422	0.646636	0.599494	0.071*
C23	0.2343 (5)	0.8518 (4)	0.9978 (3)	0.0669 (10)
C11	0.9094 (4)	0.5116 (3)	0.7059 (3)	0.0547 (8)
H11	1.019058	0.523383	0.730937	0.066*
C21	0.2365 (6)	0.3814 (4)	1.0324 (3)	0.0800 (13)
H21	0.217768	0.323987	1.071153	0.096*
C22	0.2166 (10)	0.4861 (6)	1.0545 (4)	0.138 (3)
H22A	0.233867	0.546703	1.018018	0.166*
H22B	0.184379	0.504449	1.107744	0.166*
C24	0.7974 (8)	0.3360 (6)	0.4520 (4)	0.122 (2)
H24A	0.734101	0.393304	0.476786	0.146*
H24B	0.909018	0.362895	0.472135	0.146*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Re1	0.02883 (7)	0.03518 (7)	0.03663 (7)	0.00215 (4)	0.00632 (4)	0.00003 (4)
S1	0.0313 (4)	0.0522 (5)	0.0567 (5)	−0.0028 (3)	0.0055 (3)	0.0052 (4)
S2	0.0467 (4)	0.0475 (4)	0.0498 (4)	0.0058 (3)	0.0127 (3)	0.0057 (3)
Cl1	0.0845 (8)	0.0789 (7)	0.0795 (7)	−0.0188 (6)	0.0284 (6)	−0.0051 (6)
Cl2	0.2033 (19)	0.0861 (9)	0.0820 (9)	0.0046 (10)	0.0569 (11)	0.0045 (7)
N2	0.0312 (12)	0.0355 (12)	0.0371 (12)	0.0004 (9)	0.0089 (9)	0.0011 (9)
N1	0.0341 (12)	0.0339 (12)	0.0387 (12)	0.0041 (9)	0.0092 (10)	−0.0002 (10)
N3	0.0343 (12)	0.0358 (12)	0.0424 (13)	0.0032 (10)	0.0097 (10)	−0.0002 (10)
O3	0.0432 (14)	0.0664 (16)	0.0870 (19)	−0.0157 (12)	0.0131 (13)	0.0013 (14)
O2	0.0522 (15)	0.0551 (15)	0.091 (2)	0.0124 (12)	−0.0062 (14)	0.0164 (14)
O1	0.093 (2)	0.090 (2)	0.0424 (14)	0.0082 (17)	0.0171 (14)	−0.0094 (13)
F3	0.145 (3)	0.099 (2)	0.0567 (15)	0.0050 (19)	0.0200 (16)	0.0133 (14)
O4	0.0727 (19)	0.0622 (17)	0.0759 (18)	−0.0162 (14)	0.0097 (15)	−0.0017 (14)
C9	0.0317 (14)	0.0417 (15)	0.0341 (14)	−0.0004 (11)	0.0082 (11)	−0.0011 (11)
C8	0.0325 (14)	0.0414 (15)	0.0346 (14)	0.0025 (11)	0.0101 (11)	−0.0008 (11)
O5	0.0670 (19)	0.102 (2)	0.087 (2)	0.0323 (17)	0.0270 (16)	0.0107 (18)
O6	0.083 (2)	0.0674 (18)	0.0776 (19)	0.0075 (15)	0.0170 (16)	0.0290 (15)
C15	0.0378 (15)	0.0397 (15)	0.0394 (15)	−0.0012 (12)	0.0148 (12)	−0.0004 (12)
F2	0.122 (3)	0.0708 (17)	0.108 (2)	−0.0196 (17)	−0.0141 (19)	−0.0198 (15)
F1	0.105 (2)	0.178 (4)	0.104 (2)	0.057 (2)	0.0297 (19)	−0.044 (2)
C3	0.0385 (17)	0.0475 (17)	0.0465 (17)	0.0035 (14)	0.0073 (13)	−0.0002 (13)
C2	0.0348 (16)	0.0471 (17)	0.0505 (18)	0.0008 (13)	0.0009 (13)	0.0029 (14)
C10	0.0388 (16)	0.0441 (16)	0.0432 (16)	−0.0037 (12)	0.0141 (13)	−0.0021 (13)
C7	0.0351 (16)	0.0512 (18)	0.0485 (17)	0.0080 (13)	0.0095 (13)	0.0064 (14)
C4	0.0410 (17)	0.0382 (16)	0.0531 (18)	0.0001 (13)	0.0132 (14)	0.0000 (13)
C5	0.055 (2)	0.0360 (16)	0.061 (2)	0.0048 (14)	0.0156 (16)	0.0081 (14)
C14	0.0427 (18)	0.0447 (17)	0.068 (2)	0.0018 (14)	0.0155 (16)	0.0078 (15)
C1	0.0459 (18)	0.0541 (19)	0.0436 (18)	0.0051 (14)	0.0089 (14)	0.0012 (14)
C20	0.0476 (18)	0.0407 (16)	0.0467 (17)	0.0086 (13)	0.0115 (14)	0.0052 (13)
C6	0.0481 (19)	0.0465 (18)	0.0561 (19)	0.0144 (14)	0.0112 (15)	0.0105 (14)
C12	0.064 (2)	0.0451 (19)	0.080 (3)	−0.0118 (17)	0.030 (2)	−0.0011 (17)
C18	0.058 (2)	0.062 (2)	0.0410 (17)	0.0162 (17)	0.0118 (15)	0.0019 (15)
C17	0.070 (2)	0.0442 (18)	0.060 (2)	0.0056 (16)	0.0160 (18)	−0.0093 (16)
C19	0.061 (2)	0.056 (2)	0.0453 (18)	0.0143 (16)	0.0182 (15)	0.0125 (15)
C16	0.058 (2)	0.0405 (17)	0.0521 (18)	−0.0011 (14)	0.0202 (15)	0.0009 (14)
C13	0.062 (2)	0.0415 (18)	0.080 (3)	0.0027 (16)	0.0270 (19)	0.0141 (17)
C23	0.069 (3)	0.063 (2)	0.064 (2)	0.008 (2)	0.009 (2)	−0.0054 (19)
C11	0.0492 (19)	0.0511 (19)	0.066 (2)	−0.0125 (15)	0.0207 (16)	−0.0032 (16)
C21	0.110 (4)	0.077 (3)	0.061 (2)	0.027 (3)	0.034 (2)	0.002 (2)
C22	0.242 (9)	0.098 (4)	0.105 (5)	0.026 (5)	0.104 (6)	−0.012 (4)
C24	0.098 (4)	0.119 (5)	0.114 (5)	−0.009 (4)	−0.034 (4)	−0.003 (4)

Geometric parameters (Å, º)

Re1—C2	1.900 (3)	C10—C11	1.390 (4)
Re1—C1	1.923 (3)	C7—C6	1.379 (5)
Re1—C3	1.924 (3)	C7—H7	0.9300
Re1—N2	2.189 (2)	C4—C5	1.381 (4)
Re1—N1	2.193 (2)	C4—H4	0.9300
Re1—N3	2.207 (2)	C5—C6	1.375 (5)
S1—C9	1.719 (3)	C5—H5	0.9300
S1—C10	1.733 (3)	C14—C13	1.382 (5)
S2—O5	1.424 (3)	C14—H14	0.9300
S2—O4	1.427 (3)	C20—C19	1.373 (5)
S2—O6	1.432 (3)	C20—H20	0.9300
S2—C23	1.822 (4)	C6—H6	0.9300
Cl1—C24	1.709 (6)	C12—C11	1.359 (5)
Cl2—C24	1.755 (7)	C12—C13	1.385 (6)
N2—C9	1.315 (4)	C12—H12	0.9300
N2—C15	1.405 (4)	C18—C19	1.373 (5)
N1—C4	1.341 (4)	C18—C17	1.399 (5)
N1—C8	1.363 (4)	C18—C21	1.478 (5)
N3—C16	1.346 (4)	C17—C16	1.371 (5)
N3—C20	1.346 (4)	C17—H17	0.9300
O3—C3	1.143 (4)	C19—H19	0.9300
O2—C2	1.159 (4)	C16—H16	0.9300
O1—C1	1.146 (4)	C13—H13	0.9300
F3—C23	1.312 (5)	C11—H11	0.9300
C9—C8	1.445 (4)	C21—C22	1.232 (7)
C8—C7	1.380 (4)	C21—H21	0.9300
C15—C14	1.381 (4)	C22—H22A	0.9300
C15—C10	1.396 (4)	C22—H22B	0.9300
F2—C23	1.311 (5)	C24—H24A	0.9700
F1—C23	1.310 (5)	C24—H24B	0.9700
C2—Re1—C1	87.73 (14)	C6—C5—H5	120.1
C2—Re1—C3	87.46 (14)	C4—C5—H5	120.1
C1—Re1—C3	87.51 (14)	C15—C14—C13	118.5 (3)
C2—Re1—N2	101.15 (11)	C15—C14—H14	120.8
C1—Re1—N2	95.57 (12)	C13—C14—H14	120.8
C3—Re1—N2	170.94 (11)	O1—C1—Re1	175.7 (3)
C2—Re1—N1	175.15 (11)	N3—C20—C19	123.1 (3)
C1—Re1—N1	94.91 (12)	N3—C20—H20	118.5
C3—Re1—N1	96.70 (11)	C19—C20—H20	118.5
N2—Re1—N1	74.58 (9)	C5—C6—C7	118.6 (3)
C2—Re1—N3	90.44 (12)	C5—C6—H6	120.7
C1—Re1—N3	177.94 (11)	C7—C6—H6	120.7
C3—Re1—N3	91.46 (12)	C11—C12—C13	121.6 (3)
N2—Re1—N3	85.71 (9)	C11—C12—H12	119.2
N1—Re1—N3	86.98 (9)	C13—C12—H12	119.2
C9—S1—C10	89.36 (14)	C19—C18—C17	116.2 (3)
O5—S2—O4	114.5 (2)	C19—C18—C21	120.2 (4)
O5—S2—O6	116.1 (2)	C17—C18—C21	123.5 (4)
O4—S2—O6	114.31 (18)	C16—C17—C18	119.8 (3)
O5—S2—C23	103.8 (2)	C16—C17—H17	120.1
O4—S2—C23	103.0 (2)	C18—C17—H17	120.1
O6—S2—C23	102.7 (2)	C20—C19—C18	121.0 (3)
C9—N2—C15	110.7 (2)	C20—C19—H19	119.5
C9—N2—Re1	114.97 (19)	C18—C19—H19	119.5
C15—N2—Re1	134.31 (19)	N3—C16—C17	123.8 (3)
C4—N1—C8	117.8 (2)	N3—C16—H16	118.1
C4—N1—Re1	125.6 (2)	C17—C16—H16	118.1
C8—N1—Re1	116.52 (19)	C14—C13—C12	121.0 (3)
C16—N3—C20	116.0 (3)	C14—C13—H13	119.5
C16—N3—Re1	121.4 (2)	C12—C13—H13	119.5
C20—N3—Re1	121.9 (2)	F1—C23—F2	107.3 (4)
N2—C9—C8	120.2 (3)	F1—C23—F3	108.6 (4)
N2—C9—S1	116.0 (2)	F2—C23—F3	105.1 (4)
C8—C9—S1	123.7 (2)	F1—C23—S2	110.7 (3)
N1—C8—C7	122.1 (3)	F2—C23—S2	112.7 (3)
N1—C8—C9	113.5 (2)	F3—C23—S2	112.2 (3)
C7—C8—C9	124.4 (3)	C12—C11—C10	117.7 (3)
C14—C15—C10	119.6 (3)	C12—C11—H11	121.2
C14—C15—N2	126.9 (3)	C10—C11—H11	121.2
C10—C15—N2	113.5 (3)	C22—C21—C18	126.4 (5)
O3—C3—Re1	179.7 (4)	C22—C21—H21	116.8
O2—C2—Re1	179.2 (3)	C18—C21—H21	116.8
C11—C10—C15	121.6 (3)	C21—C22—H22A	120.0
C11—C10—S1	128.0 (3)	C21—C22—H22B	120.0
C15—C10—S1	110.4 (2)	H22A—C22—H22B	120.0
C6—C7—C8	119.4 (3)	Cl1—C24—Cl2	113.9 (3)
C6—C7—H7	120.3	Cl1—C24—H24A	108.8
C8—C7—H7	120.3	Cl2—C24—H24A	108.8
N1—C4—C5	122.2 (3)	Cl1—C24—H24B	108.8
N1—C4—H4	118.9	Cl2—C24—H24B	108.8
C5—C4—H4	118.9	H24A—C24—H24B	107.7
C6—C5—C4	119.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O6^i	0.93	2.65	3.333 (5)	131
C5—H5···O5^i	0.93	2.65	3.278 (5)	125
C20—H20···O6^i	0.93	2.50	3.336 (4)	150
C11—H11···Cl1^ii	0.93	2.98	3.640 (4)	129
C24—H24B···O2^iii	0.97	2.28	3.189 (6)	156

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

fac-Tricarbonyl[2-(quinolin-2-yl)-1,3-benzothiazole-κ²N,N'](4-vinylpyridine-κN)rhenium(I) trifluoromethanesulfonate 0.28-hydrate (2)

Crystal data

[Re(C7H7N)(C16H10N2S)(CO)3](CF3SO3)·0.28H2O	F(000) = 1537
Mr = 791.20	Dx = 1.872 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.814 (3) Å	Cell parameters from 5353 reflections
b = 12.088 (2) Å	θ = 2.3–22.0°
c = 18.248 (4) Å	µ = 4.55 mm^−1
β = 96.56 (3)°	T = 273 K
V = 2808.0 (10) Å^3	Block, yellow
Z = 4	0.15 × 0.12 × 0.10 mm

Data collection

Bruker APEXII diffractometer	7054 independent reflections
Radiation source: fine-focus sealed tube	5250 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
Detector resolution: 8.33 pixels mm^-1	θmax = 29.1°, θmin = 2.3°
ω–scans	h = −17→16
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −16→13
Tmin = 0.611, Tmax = 0.746	l = −23→24
25681 measured reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.104	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.050P)^2] where P = (Fo^2 + 2Fc^2)/3
7054 reflections	(Δ/σ)max = 0.001
608 parameters	Δρmax = 1.22 e Å^−3
3097 restraints	Δρmin = −0.71 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Re1	0.18897 (2)	0.26296 (2)	0.39241 (2)	0.05208 (9)
S1	0.37198 (12)	0.57697 (13)	0.46845 (9)	0.0829 (4)
O1	0.0100 (3)	0.3433 (4)	0.2797 (2)	0.0931 (13)
O2	0.0742 (3)	0.0468 (4)	0.4173 (2)	0.0972 (13)
O3	0.2720 (3)	0.1400 (3)	0.2651 (2)	0.0839 (12)
N1	0.1402 (3)	0.3616 (3)	0.48547 (19)	0.0536 (9)
N2	0.2845 (3)	0.4122 (3)	0.3965 (2)	0.0524 (9)
N3	0.3207 (3)	0.2054 (3)	0.4725 (2)	0.0536 (9)
C1	0.0766 (4)	0.3141 (5)	0.3229 (3)	0.0664 (13)
C2	0.1145 (4)	0.1283 (5)	0.4077 (3)	0.0661 (13)
C3	0.2425 (4)	0.1860 (5)	0.3133 (3)	0.0633 (13)
C4	0.0567 (3)	0.3445 (4)	0.5259 (2)	0.0556 (12)
C5	−0.0243 (4)	0.2712 (5)	0.5001 (3)	0.0714 (15)
H5	−0.022553	0.234203	0.455581	0.086*
C6	−0.1065 (5)	0.2546 (5)	0.5414 (4)	0.085 (2)
H6	−0.160797	0.207137	0.523809	0.102*
C7	−0.1100 (5)	0.3063 (6)	0.6078 (3)	0.0845 (18)
H7	−0.165381	0.291519	0.635206	0.101*
C8	−0.0341 (4)	0.3786 (6)	0.6343 (3)	0.0766 (16)
H8	−0.037283	0.413413	0.679488	0.092*
C9	0.0510 (4)	0.4009 (5)	0.5922 (3)	0.0640 (13)
C10	0.1287 (5)	0.4786 (5)	0.6140 (3)	0.0836 (17)
H10	0.128062	0.513484	0.659400	0.100*
C11	0.1991 (4)	0.5031 (5)	0.5750 (3)	0.0690 (14)
H11	0.246414	0.559566	0.589372	0.083*
C12	0.2066 (4)	0.4439 (4)	0.5082 (3)	0.0599 (12)
C13	0.2836 (3)	0.4692 (4)	0.4578 (3)	0.0556 (11)
C14	0.4164 (4)	0.5428 (5)	0.3845 (3)	0.0693 (14)
C15	0.4942 (5)	0.5909 (5)	0.3493 (4)	0.093 (2)
H15	0.531174	0.651887	0.369518	0.112*
C16	0.5157 (5)	0.5470 (6)	0.2841 (4)	0.099 (2)
H16	0.569143	0.577862	0.260319	0.119*
C17	0.4602 (5)	0.4574 (6)	0.2518 (3)	0.0870 (18)
H17	0.476478	0.429812	0.206946	0.104*
C18	0.3813 (4)	0.4092 (5)	0.2860 (3)	0.0670 (13)
H18	0.343376	0.349676	0.264386	0.080*
C19	0.3595 (3)	0.4513 (4)	0.3535 (3)	0.0572 (12)
C20	0.4174 (4)	0.2054 (4)	0.4533 (3)	0.0595 (12)
H20	0.428930	0.234653	0.407761	0.071*
C21	0.5021 (4)	0.1629 (4)	0.4991 (3)	0.0608 (12)
H21	0.568913	0.164295	0.483929	0.073*
C22	0.4876 (4)	0.1188 (4)	0.5668 (3)	0.0599 (12)
C23	0.3873 (4)	0.1202 (5)	0.5863 (3)	0.0689 (14)
H23	0.373901	0.092280	0.631744	0.083*
C24	0.3060 (4)	0.1633 (4)	0.5381 (3)	0.0630 (13)
H24	0.238452	0.162822	0.552115	0.076*
C25	0.5758 (5)	0.0727 (5)	0.6174 (3)	0.0765 (16)
H25	0.559334	0.034776	0.658917	0.092*
C26	0.6734 (5)	0.0817 (6)	0.6079 (4)	0.105 (2)
H26A	0.692590	0.119085	0.566965	0.126*
H26B	0.724685	0.050676	0.641911	0.126*
S2	0.8300 (7)	0.6914 (9)	0.1685 (6)	0.1007 (17)	0.375 (3)
O4	0.9064 (10)	0.6143 (12)	0.1993 (7)	0.115 (2)	0.375 (3)
O5	0.8707 (11)	0.7853 (12)	0.1333 (7)	0.114 (2)	0.375 (3)
O6	0.7354 (10)	0.6459 (11)	0.1317 (7)	0.118 (2)	0.375 (3)
C27	0.7805 (8)	0.7566 (10)	0.2528 (9)	0.113 (2)	0.375 (3)
F1	0.7387 (9)	0.6762 (10)	0.2851 (6)	0.121 (2)	0.375 (3)
F2	0.7133 (8)	0.8304 (9)	0.2281 (6)	0.121 (2)	0.375 (3)
F3	0.8604 (9)	0.7971 (9)	0.2914 (6)	0.113 (2)	0.375 (3)
S2A	0.7824 (9)	0.6799 (11)	0.1667 (6)	0.106 (2)	0.222 (3)
O4A	0.807 (2)	0.734 (2)	0.1028 (11)	0.114 (2)	0.222 (3)
O5A	0.6703 (14)	0.649 (2)	0.1560 (14)	0.118 (2)	0.222 (3)
O6A	0.8457 (19)	0.5846 (18)	0.1929 (13)	0.116 (2)	0.222 (3)
C27A	0.7903 (18)	0.7705 (19)	0.2512 (12)	0.114 (2)	0.222 (3)
F1A	0.8879 (16)	0.7603 (18)	0.2795 (13)	0.119 (2)	0.222 (3)
F2A	0.7250 (18)	0.7329 (17)	0.2936 (12)	0.114 (2)	0.222 (3)
F3A	0.7706 (17)	0.8700 (15)	0.2263 (11)	0.118 (2)	0.222 (3)
S2B	0.8443 (10)	0.6936 (14)	0.1676 (10)	0.1060 (19)	0.279 (2)
O4B	0.842 (2)	0.771 (2)	0.1111 (11)	0.114 (2)	0.279 (2)
O5B	0.9332 (14)	0.6202 (19)	0.1765 (11)	0.112 (2)	0.279 (2)
O6B	0.831 (2)	0.7428 (16)	0.2396 (10)	0.119 (2)	0.279 (2)
C27B	0.7202 (17)	0.6139 (17)	0.1428 (11)	0.115 (2)	0.279 (2)
F1B	0.6484 (11)	0.6935 (14)	0.1429 (9)	0.115 (2)	0.279 (2)
F2B	0.7244 (12)	0.5376 (13)	0.1873 (8)	0.120 (2)	0.279 (2)
F3B	0.7442 (12)	0.5872 (14)	0.0776 (7)	0.121 (2)	0.279 (2)
O7	0.8510 (15)	0.9029 (18)	0.3628 (10)	0.129 (3)	0.279 (2)
C27C	0.7802 (16)	0.7569 (15)	0.2269 (10)	0.117 (2)	0.125 (2)
O4C	0.797 (3)	0.733 (3)	0.3024 (12)	0.115 (2)	0.125 (2)
O5C	0.672 (2)	0.759 (3)	0.193 (2)	0.114 (2)	0.125 (2)
O6C	0.836 (3)	0.855 (2)	0.2047 (19)	0.115 (2)	0.125 (2)
S2C	0.840 (2)	0.644 (2)	0.1740 (15)	0.115 (2)	0.125 (2)
F1C	0.940 (2)	0.667 (3)	0.191 (2)	0.113 (2)	0.125 (2)
F2C	0.807 (3)	0.655 (3)	0.1059 (13)	0.116 (2)	0.125 (2)
F3C	0.801 (3)	0.564 (2)	0.2102 (17)	0.117 (2)	0.125 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Re1	0.05839 (13)	0.05183 (15)	0.04699 (13)	−0.00752 (8)	0.01014 (9)	−0.00218 (8)
S1	0.0777 (9)	0.0666 (10)	0.1048 (12)	−0.0156 (7)	0.0120 (8)	−0.0168 (8)
O1	0.082 (3)	0.117 (4)	0.077 (3)	0.008 (3)	−0.004 (2)	0.007 (3)
O2	0.118 (3)	0.073 (3)	0.106 (3)	−0.036 (3)	0.033 (3)	−0.010 (2)
O3	0.099 (3)	0.087 (3)	0.073 (2)	−0.020 (2)	0.039 (2)	−0.019 (2)
N1	0.054 (2)	0.058 (3)	0.049 (2)	0.0052 (18)	0.0079 (17)	−0.0007 (18)
N2	0.056 (2)	0.051 (2)	0.051 (2)	−0.0007 (18)	0.0098 (17)	0.0068 (18)
N3	0.069 (3)	0.042 (2)	0.052 (2)	0.0031 (19)	0.0122 (19)	−0.0009 (18)
C1	0.072 (3)	0.068 (4)	0.060 (3)	−0.007 (3)	0.014 (3)	−0.001 (3)
C2	0.079 (3)	0.063 (4)	0.057 (3)	−0.017 (3)	0.014 (3)	−0.008 (3)
C3	0.077 (3)	0.064 (4)	0.052 (3)	−0.016 (3)	0.020 (2)	−0.005 (2)
C4	0.052 (3)	0.065 (3)	0.050 (3)	0.003 (2)	0.009 (2)	0.006 (2)
C5	0.065 (3)	0.084 (4)	0.067 (3)	−0.005 (3)	0.018 (3)	−0.010 (3)
C6	0.074 (4)	0.094 (5)	0.092 (5)	−0.014 (3)	0.029 (4)	−0.006 (3)
C7	0.086 (4)	0.097 (5)	0.077 (4)	0.000 (4)	0.040 (3)	0.020 (4)
C8	0.082 (4)	0.095 (5)	0.057 (3)	0.015 (3)	0.025 (3)	0.004 (3)
C9	0.069 (3)	0.069 (4)	0.055 (3)	0.006 (3)	0.012 (2)	0.001 (2)
C10	0.080 (4)	0.086 (5)	0.084 (4)	0.000 (3)	0.003 (3)	−0.025 (3)
C11	0.085 (4)	0.060 (4)	0.062 (3)	−0.003 (3)	0.007 (3)	−0.023 (3)
C12	0.062 (3)	0.055 (3)	0.063 (3)	0.003 (2)	0.008 (2)	−0.001 (2)
C13	0.056 (3)	0.047 (3)	0.064 (3)	−0.003 (2)	0.006 (2)	0.000 (2)
C14	0.059 (3)	0.058 (3)	0.092 (4)	−0.003 (3)	0.013 (3)	0.011 (3)
C15	0.076 (4)	0.070 (4)	0.138 (6)	−0.014 (3)	0.036 (4)	0.009 (4)
C16	0.073 (4)	0.096 (5)	0.136 (6)	−0.001 (4)	0.045 (4)	0.043 (5)
C17	0.091 (4)	0.088 (5)	0.087 (4)	0.010 (4)	0.034 (3)	0.028 (4)
C18	0.077 (3)	0.062 (3)	0.064 (3)	−0.001 (3)	0.014 (3)	0.009 (3)
C19	0.053 (3)	0.048 (3)	0.070 (3)	0.001 (2)	0.009 (2)	0.012 (2)
C20	0.065 (3)	0.059 (3)	0.056 (3)	−0.005 (3)	0.011 (2)	0.004 (2)
C21	0.059 (3)	0.064 (3)	0.061 (3)	−0.009 (2)	0.012 (2)	−0.004 (2)
C22	0.072 (3)	0.045 (3)	0.061 (3)	0.004 (2)	0.002 (3)	−0.006 (2)
C23	0.085 (4)	0.071 (4)	0.051 (3)	0.001 (3)	0.011 (3)	0.010 (3)
C24	0.069 (3)	0.060 (3)	0.063 (3)	−0.003 (3)	0.022 (3)	0.002 (2)
C25	0.092 (4)	0.067 (4)	0.069 (4)	0.012 (3)	0.005 (3)	0.001 (3)
C26	0.076 (4)	0.110 (6)	0.126 (6)	−0.007 (4)	−0.004 (4)	0.035 (5)
S2	0.114 (4)	0.107 (3)	0.081 (3)	0.043 (3)	0.013 (3)	0.006 (2)
O4	0.116 (4)	0.128 (4)	0.103 (4)	0.042 (4)	0.017 (4)	0.007 (4)
O5	0.118 (4)	0.129 (4)	0.099 (4)	0.033 (4)	0.023 (4)	0.014 (4)
O6	0.116 (4)	0.135 (4)	0.104 (4)	0.031 (4)	0.023 (4)	0.006 (4)
C27	0.113 (4)	0.128 (4)	0.101 (4)	0.035 (4)	0.024 (4)	0.013 (4)
F1	0.119 (4)	0.132 (4)	0.114 (4)	0.020 (4)	0.022 (4)	0.024 (4)
F2	0.116 (4)	0.133 (4)	0.116 (4)	0.045 (4)	0.027 (4)	0.013 (4)
F3	0.113 (4)	0.120 (4)	0.107 (4)	0.032 (4)	0.017 (4)	−0.004 (4)
S2A	0.113 (4)	0.121 (4)	0.089 (3)	0.032 (4)	0.031 (4)	0.007 (3)
O4A	0.117 (5)	0.126 (5)	0.102 (4)	0.035 (4)	0.023 (4)	0.014 (4)
O5A	0.120 (4)	0.130 (4)	0.106 (4)	0.032 (4)	0.020 (4)	0.010 (4)
O6A	0.118 (4)	0.128 (4)	0.105 (4)	0.033 (4)	0.024 (4)	0.007 (4)
C27A	0.115 (4)	0.128 (4)	0.102 (4)	0.036 (4)	0.023 (4)	0.010 (4)
F1A	0.117 (4)	0.130 (5)	0.109 (4)	0.029 (4)	0.016 (4)	0.005 (4)
F2A	0.117 (4)	0.124 (5)	0.104 (4)	0.033 (4)	0.029 (4)	0.007 (4)
F3A	0.121 (5)	0.124 (4)	0.110 (4)	0.031 (4)	0.019 (4)	0.010 (4)
S2B	0.112 (4)	0.112 (4)	0.095 (3)	0.043 (3)	0.016 (3)	0.008 (3)
O4B	0.117 (5)	0.127 (4)	0.102 (4)	0.033 (4)	0.024 (4)	0.014 (4)
O5B	0.111 (4)	0.127 (4)	0.100 (4)	0.037 (4)	0.023 (4)	0.012 (4)
O6B	0.120 (5)	0.132 (4)	0.105 (4)	0.039 (4)	0.018 (4)	0.009 (4)
C27B	0.116 (4)	0.130 (4)	0.102 (4)	0.034 (4)	0.023 (4)	0.011 (4)
F1B	0.114 (4)	0.128 (4)	0.106 (4)	0.040 (4)	0.017 (4)	0.014 (4)
F2B	0.117 (4)	0.129 (4)	0.115 (4)	0.033 (4)	0.022 (4)	0.017 (4)
F3B	0.124 (5)	0.134 (5)	0.107 (4)	0.036 (4)	0.018 (4)	0.002 (4)
O7	0.128 (6)	0.145 (6)	0.117 (6)	0.026 (6)	0.026 (6)	0.008 (6)
C27C	0.115 (4)	0.130 (4)	0.107 (4)	0.039 (4)	0.024 (4)	0.011 (4)
O4C	0.117 (5)	0.127 (5)	0.104 (4)	0.036 (4)	0.020 (4)	0.010 (4)
O5C	0.114 (4)	0.127 (5)	0.104 (4)	0.035 (4)	0.021 (4)	0.007 (4)
O6C	0.116 (5)	0.128 (4)	0.105 (4)	0.034 (4)	0.023 (4)	0.009 (4)
S2C	0.116 (4)	0.127 (4)	0.103 (4)	0.035 (4)	0.022 (4)	0.010 (4)
F1C	0.114 (4)	0.127 (5)	0.102 (4)	0.036 (4)	0.023 (4)	0.011 (4)
F2C	0.117 (5)	0.128 (5)	0.105 (4)	0.034 (4)	0.022 (4)	0.009 (4)
F3C	0.118 (5)	0.127 (4)	0.106 (4)	0.033 (4)	0.020 (4)	0.010 (4)

Geometric parameters (Å, º)

Re1—C3	1.909 (5)	C18—H18	0.9300
Re1—C1	1.910 (6)	C20—C21	1.390 (7)
Re1—C2	1.924 (6)	C20—H20	0.9300
Re1—N2	2.176 (4)	C21—C22	1.377 (7)
Re1—N3	2.214 (4)	C21—H21	0.9300
Re1—N1	2.222 (4)	C22—C23	1.373 (7)
S1—C13	1.723 (5)	C22—C25	1.484 (7)
S1—C14	1.744 (6)	C23—C24	1.385 (7)
O1—C1	1.149 (6)	C23—H23	0.9300
O2—C2	1.135 (6)	C24—H24	0.9300
O3—C3	1.142 (5)	C25—C26	1.287 (8)
N1—C12	1.343 (6)	C25—H25	0.9300
N1—C4	1.384 (5)	C26—H26A	0.9300
N2—C13	1.315 (6)	C26—H26B	0.9300
N2—C19	1.391 (5)	S2—O4	1.420 (8)
N3—C20	1.326 (6)	S2—O6	1.427 (9)
N3—C24	1.335 (6)	S2—O5	1.432 (8)
C4—C9	1.397 (6)	S2—C27	1.90 (2)
C4—C5	1.405 (7)	C27—F3	1.272 (9)
C5—C6	1.378 (8)	C27—F1	1.284 (9)
C5—H5	0.9300	C27—F2	1.286 (9)
C6—C7	1.369 (9)	S2A—O4A	1.402 (15)
C6—H6	0.9300	S2A—O6A	1.458 (16)
C7—C8	1.356 (8)	S2A—O5A	1.475 (16)
C7—H7	0.9300	S2A—C27A	1.88 (2)
C8—C9	1.430 (7)	C27A—F2A	1.285 (18)
C8—H8	0.9300	C27A—F3A	1.300 (18)
C9—C10	1.394 (8)	C27A—F1A	1.303 (19)
C10—C11	1.247 (7)	S2B—O4B	1.394 (14)
C10—H10	0.9300	S2B—O5B	1.438 (14)
C11—C12	1.427 (6)	S2B—O6B	1.471 (18)
C11—H11	0.9300	S2B—C27B	1.87 (2)
C12—C13	1.455 (6)	C27B—F2B	1.225 (17)
C14—C15	1.375 (7)	C27B—F3B	1.304 (18)
C14—C19	1.408 (7)	C27B—F1B	1.331 (17)
C15—C16	1.359 (9)	C27C—O4C	1.399 (17)
C15—H15	0.9300	C27C—O5C	1.457 (17)
C16—C17	1.388 (9)	C27C—O6C	1.466 (18)
C16—H16	0.9300	C27C—S2C	1.88 (2)
C17—C18	1.377 (7)	S2C—F2C	1.271 (19)
C17—H17	0.9300	S2C—F3C	1.307 (19)
C18—C19	1.390 (7)	S2C—F1C	1.321 (19)
C3—Re1—C1	87.9 (2)	C18—C19—N2	126.7 (5)
C3—Re1—C2	85.7 (2)	C18—C19—C14	119.7 (5)
C1—Re1—C2	91.2 (2)	N2—C19—C14	113.6 (5)
C3—Re1—N2	100.42 (18)	N3—C20—C21	122.0 (5)
C1—Re1—N2	97.63 (19)	N3—C20—H20	119.0
C2—Re1—N2	169.40 (18)	C21—C20—H20	119.0
C3—Re1—N3	91.92 (19)	C22—C21—C20	120.5 (5)
C1—Re1—N3	179.21 (19)	C22—C21—H21	119.8
C2—Re1—N3	89.5 (2)	C20—C21—H21	119.8
N2—Re1—N3	81.63 (14)	C23—C22—C21	117.0 (5)
C3—Re1—N1	174.73 (18)	C23—C22—C25	120.8 (5)
C1—Re1—N1	94.45 (18)	C21—C22—C25	122.2 (5)
C2—Re1—N1	98.97 (18)	C22—C23—C24	119.9 (5)
N2—Re1—N1	74.63 (14)	C22—C23—H23	120.0
N3—Re1—N1	85.63 (13)	C24—C23—H23	120.0
C13—S1—C14	89.9 (2)	N3—C24—C23	122.7 (5)
C12—N1—C4	116.6 (4)	N3—C24—H24	118.7
C12—N1—Re1	114.2 (3)	C23—C24—H24	118.7
C4—N1—Re1	129.0 (3)	C26—C25—C22	124.5 (6)
C13—N2—C19	112.1 (4)	C26—C25—H25	117.7
C13—N2—Re1	113.8 (3)	C22—C25—H25	117.7
C19—N2—Re1	133.2 (3)	C25—C26—H26A	120.0
C20—N3—C24	118.0 (4)	C25—C26—H26B	120.0
C20—N3—Re1	119.4 (3)	H26A—C26—H26B	120.0
C24—N3—Re1	122.5 (3)	O4—S2—O6	116.4 (7)
O1—C1—Re1	178.2 (5)	O4—S2—O5	115.3 (6)
O2—C2—Re1	177.3 (5)	O6—S2—O5	115.3 (7)
O3—C3—Re1	178.3 (5)	O4—S2—C27	103.3 (7)
N1—C4—C9	120.6 (4)	O6—S2—C27	101.3 (7)
N1—C4—C5	120.2 (4)	O5—S2—C27	101.9 (7)
C9—C4—C5	119.2 (4)	F3—C27—F1	113.0 (10)
C6—C5—C4	119.4 (6)	F3—C27—F2	113.0 (10)
C6—C5—H5	120.3	F1—C27—F2	112.9 (10)
C4—C5—H5	120.3	F3—C27—S2	106.6 (10)
C7—C6—C5	121.5 (6)	F1—C27—S2	104.6 (10)
C7—C6—H6	119.2	F2—C27—S2	106.0 (10)
C5—C6—H6	119.2	O4A—S2A—O6A	118.1 (16)
C8—C7—C6	121.0 (5)	O4A—S2A—O5A	108.2 (15)
C8—C7—H7	119.5	O6A—S2A—O5A	110.0 (15)
C6—C7—H7	119.5	O4A—S2A—C27A	114.5 (15)
C7—C8—C9	119.3 (5)	O6A—S2A—C27A	102.4 (12)
C7—C8—H8	120.3	O5A—S2A—C27A	102.5 (12)
C9—C8—H8	120.3	F2A—C27A—F3A	115 (2)
C10—C9—C4	118.0 (5)	F2A—C27A—F1A	113 (2)
C10—C9—C8	122.5 (5)	F3A—C27A—F1A	111 (2)
C4—C9—C8	119.5 (5)	F2A—C27A—S2A	108.0 (17)
C11—C10—C9	122.5 (6)	F3A—C27A—S2A	105.1 (15)
C11—C10—H10	118.8	F1A—C27A—S2A	103.2 (16)
C9—C10—H10	118.8	O4B—S2B—O5B	116.5 (15)
C10—C11—C12	119.5 (5)	O4B—S2B—O6B	113.2 (17)
C10—C11—H11	120.3	O5B—S2B—O6B	108.7 (14)
C12—C11—H11	120.3	O4B—S2B—C27B	103.1 (13)
N1—C12—C11	122.3 (4)	O5B—S2B—C27B	110.5 (13)
N1—C12—C13	114.3 (4)	O6B—S2B—C27B	104.0 (12)
C11—C12—C13	123.4 (5)	F2B—C27B—F3B	114.9 (18)
N2—C13—C12	120.0 (4)	F2B—C27B—F1B	121.4 (18)
N2—C13—S1	115.0 (3)	F3B—C27B—F1B	114.5 (17)
C12—C13—S1	124.9 (4)	F2B—C27B—S2B	104.8 (16)
C15—C14—C19	121.0 (6)	F3B—C27B—S2B	93.8 (14)
C15—C14—S1	129.6 (5)	F1B—C27B—S2B	101.3 (15)
C19—C14—S1	109.4 (4)	O4C—C27C—O5C	117 (2)
C16—C15—C14	118.3 (6)	O4C—C27C—O6C	114 (2)
C16—C15—H15	120.9	O5C—C27C—O6C	110.1 (18)
C14—C15—H15	120.9	O4C—C27C—S2C	109.5 (17)
C15—C16—C17	122.0 (6)	O5C—C27C—S2C	102.4 (16)
C15—C16—H16	119.0	O6C—C27C—S2C	101.7 (15)
C17—C16—H16	119.0	F2C—S2C—F3C	118 (2)
C18—C17—C16	120.4 (6)	F2C—S2C—F1C	114 (2)
C18—C17—H17	119.8	F3C—S2C—F1C	117 (2)
C16—C17—H17	119.8	F2C—S2C—C27C	109 (2)
C17—C18—C19	118.6 (6)	F3C—S2C—C27C	94.5 (18)
C17—C18—H18	120.7	F1C—S2C—C27C	99.8 (19)
C19—C18—H18	120.7

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···F1B^i	0.93	2.33	3.045 (17)	134
C11—H11···O5^ii	0.93	2.53	3.459 (16)	178
C11—H11···O4A^ii	0.93	2.62	3.48 (3)	154
C11—H11···F3A^ii	0.93	2.62	3.199 (19)	121
C11—H11···O4B^ii	0.93	2.39	3.31 (3)	168
C11—H11···O6C^ii	0.93	2.50	3.27 (3)	140
C21—H21···O4A^iii	0.93	2.52	3.35 (3)	150
C21—H21···O4B^iii	0.93	2.53	3.26 (3)	136
C21—H21···F2C^iii	0.93	2.41	3.27 (3)	154
C23—H23···O6A^iv	0.93	2.46	3.23 (2)	141
C23—H23···F3C^iv	0.93	2.61	3.44 (3)	150
C24—H24···O7^v	0.93	2.18	2.96 (2)	141

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

fac-Tricarbonyl[1,10-phenanthroline-κ²N,N'](4-vinylpyridine-κN)rhenium(I) trifluoromethanesulfonate (3)

Crystal data

[Re(C7H7N)(C12H8N2)(CO)3](CF3SO3)	F(000) = 1360
Mr = 704.64	Dx = 1.905 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.398 (2) Å	Cell parameters from 9930 reflections
b = 12.878 (3) Å	θ = 2.6–29.0°
c = 15.393 (3) Å	µ = 5.10 mm^−1
β = 91.83 (3)°	T = 296 K
V = 2456.5 (8) Å^3	Block, yellow
Z = 4	0.18 × 0.15 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer	5011 independent reflections
Radiation source: fine-focus sealed tube	4517 reflections with I > 2σ(I)
Detector resolution: 8.33 pixels mm^-1	Rint = 0.019
ω scans	θmax = 26.4°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −15→15
Tmin = 0.490, Tmax = 0.746	k = −16→16
23150 measured reflections	l = −19→19

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.019	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.046	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0207P)^2 + 1.7702P] where P = (Fo^2 + 2Fc^2)/3
5011 reflections	(Δ/σ)max = 0.002
481 parameters	Δρmax = 1.23 e Å^−3
913 restraints	Δρmin = −0.58 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Re1	0.42304 (2)	0.73137 (2)	0.21775 (2)	0.04579 (5)
N2	0.52880 (17)	0.60262 (17)	0.18745 (14)	0.0461 (5)
N1	0.32397 (17)	0.63066 (19)	0.13343 (13)	0.0490 (5)
O2	0.2581 (2)	0.9037 (2)	0.24925 (16)	0.0818 (7)
N3	0.35773 (17)	0.63088 (17)	0.32066 (13)	0.0466 (5)
C15	0.3724 (2)	0.5393 (2)	0.11144 (15)	0.0464 (6)
O1	0.5148 (2)	0.8662 (2)	0.07393 (17)	0.0877 (8)
O3	0.5783 (2)	0.8415 (2)	0.34638 (19)	0.0982 (9)
C14	0.4820 (2)	0.5247 (2)	0.13976 (16)	0.0448 (6)
C7	0.3203 (2)	0.4620 (3)	0.06156 (18)	0.0567 (7)
C2	0.3188 (3)	0.8387 (2)	0.23759 (18)	0.0580 (7)
C20	0.2551 (2)	0.6396 (2)	0.3453 (2)	0.0607 (7)
H20	0.210874	0.688240	0.317122	0.073*
C19	0.2123 (3)	0.5804 (3)	0.4098 (2)	0.0664 (8)
H19	0.141084	0.590569	0.425005	0.080*
C13	0.6335 (2)	0.5932 (2)	0.20978 (19)	0.0563 (7)
H13	0.666811	0.646533	0.241302	0.068*
C18	0.2744 (3)	0.5058 (2)	0.45257 (18)	0.0571 (7)
C10	0.5384 (2)	0.4349 (2)	0.11669 (18)	0.0552 (7)
C1	0.4799 (3)	0.8149 (3)	0.1269 (2)	0.0604 (7)
C12	0.6942 (2)	0.5077 (3)	0.1880 (2)	0.0641 (8)
H12	0.767046	0.504596	0.204320	0.077*
C9	0.4823 (3)	0.3574 (3)	0.0673 (2)	0.0684 (8)
H9	0.518101	0.296642	0.052968	0.082*
C3	0.5199 (3)	0.8009 (3)	0.2981 (2)	0.0632 (8)
C8	0.3792 (3)	0.3698 (3)	0.0411 (2)	0.0677 (9)
H8	0.344987	0.317500	0.008962	0.081*
C11	0.6476 (3)	0.4288 (3)	0.1431 (2)	0.0635 (8)
H11	0.687850	0.370323	0.129574	0.076*
C17	0.3790 (2)	0.4955 (3)	0.42603 (19)	0.0631 (8)
H17	0.423950	0.445522	0.451611	0.076*
C16	0.4171 (2)	0.5585 (3)	0.36214 (18)	0.0581 (7)
H16	0.488537	0.550375	0.346690	0.070*
C4	0.2222 (2)	0.6453 (3)	0.10613 (19)	0.0653 (8)
H4	0.187874	0.706757	0.120904	0.078*
C5	0.1650 (3)	0.5721 (4)	0.0561 (2)	0.0781 (10)
H5	0.094063	0.585208	0.037845	0.094*
C6	0.2133 (3)	0.4815 (3)	0.0343 (2)	0.0727 (9)
H6	0.175402	0.432423	0.001228	0.087*
C21	0.2291 (3)	0.4412 (3)	0.5215 (2)	0.0742 (9)
H21	0.162916	0.461253	0.542885	0.089*
C22	0.2735 (4)	0.3597 (4)	0.5546 (3)	0.0947 (13)
H22A	0.339705	0.337111	0.534996	0.114*
H22B	0.239484	0.323226	0.598042	0.114*
S1	0.9375 (10)	0.7116 (11)	0.1976 (8)	0.065 (2)	0.338 (3)
O4	1.0403 (16)	0.763 (2)	0.2104 (18)	0.088 (6)	0.338 (3)
O5	0.935 (3)	0.6151 (16)	0.1495 (17)	0.099 (7)	0.338 (3)
O6	0.867 (2)	0.717 (2)	0.2706 (15)	0.067 (5)	0.338 (3)
C23	0.8688 (15)	0.7977 (18)	0.1175 (13)	0.077 (4)	0.338 (3)
F1	0.874 (2)	0.8943 (16)	0.142 (2)	0.112 (7)	0.338 (3)
F2	0.7677 (13)	0.774 (2)	0.1097 (16)	0.128 (7)	0.338 (3)
F3	0.9157 (14)	0.7899 (19)	0.0422 (11)	0.113 (5)	0.338 (3)
S1A	0.8979 (4)	0.7746 (4)	0.1201 (5)	0.0665 (14)	0.345 (3)
O4A	0.904 (3)	0.8784 (13)	0.1573 (18)	0.107 (8)	0.345 (3)
O5A	0.7913 (13)	0.7302 (15)	0.1055 (15)	0.103 (5)	0.345 (3)
O6A	0.9783 (19)	0.7510 (19)	0.0562 (14)	0.104 (6)	0.345 (3)
C23A	0.9499 (16)	0.6969 (16)	0.2134 (14)	0.078 (4)	0.345 (3)
F1A	0.8853 (19)	0.697 (2)	0.2776 (14)	0.093 (6)	0.345 (3)
F2A	1.0429 (17)	0.730 (2)	0.2428 (18)	0.122 (7)	0.345 (3)
F3A	0.9658 (14)	0.6012 (11)	0.1916 (8)	0.117 (4)	0.345 (3)
S1B	0.9353 (9)	0.6983 (12)	0.2016 (8)	0.060 (2)	0.317 (3)
O4B	1.0393 (16)	0.740 (2)	0.2292 (19)	0.074 (6)	0.317 (3)
O5B	0.938 (2)	0.6004 (15)	0.1562 (19)	0.080 (6)	0.317 (3)
O6B	0.847 (2)	0.715 (3)	0.2596 (17)	0.084 (7)	0.317 (3)
C23B	0.8960 (16)	0.7879 (17)	0.1123 (14)	0.065 (4)	0.317 (3)
F1B	0.896 (2)	0.8851 (14)	0.1382 (16)	0.074 (4)	0.317 (3)
F2B	0.7981 (14)	0.767 (2)	0.0835 (14)	0.119 (6)	0.317 (3)
F3B	0.9622 (19)	0.7795 (18)	0.0484 (14)	0.098 (6)	0.317 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Re1	0.05067 (7)	0.04491 (7)	0.04193 (7)	0.00107 (4)	0.00364 (4)	0.00007 (4)
N2	0.0446 (12)	0.0493 (13)	0.0448 (11)	−0.0015 (9)	0.0067 (9)	0.0027 (9)
N1	0.0453 (12)	0.0623 (14)	0.0395 (11)	0.0006 (10)	0.0040 (9)	−0.0011 (10)
O2	0.1036 (19)	0.0689 (15)	0.0740 (15)	0.0352 (14)	0.0189 (13)	0.0060 (12)
N3	0.0498 (12)	0.0497 (13)	0.0404 (11)	0.0018 (10)	0.0036 (9)	0.0000 (9)
C15	0.0529 (15)	0.0526 (15)	0.0344 (12)	−0.0067 (12)	0.0105 (10)	0.0016 (11)
O1	0.0976 (19)	0.0872 (18)	0.0798 (16)	−0.0107 (15)	0.0258 (14)	0.0259 (14)
O3	0.107 (2)	0.0866 (19)	0.099 (2)	−0.0201 (16)	−0.0338 (16)	−0.0172 (16)
C14	0.0491 (14)	0.0470 (14)	0.0388 (12)	−0.0042 (11)	0.0096 (10)	0.0044 (10)
C7	0.0617 (18)	0.0679 (19)	0.0408 (14)	−0.0148 (14)	0.0056 (12)	−0.0006 (13)
C2	0.075 (2)	0.0554 (17)	0.0433 (14)	0.0049 (15)	0.0064 (13)	0.0038 (12)
C20	0.0604 (18)	0.0581 (18)	0.0644 (18)	0.0136 (14)	0.0142 (14)	0.0066 (14)
C19	0.0613 (19)	0.069 (2)	0.070 (2)	0.0053 (15)	0.0228 (15)	0.0020 (16)
C13	0.0458 (15)	0.0622 (18)	0.0611 (17)	−0.0028 (13)	0.0042 (12)	0.0057 (14)
C18	0.0666 (18)	0.0613 (18)	0.0439 (14)	−0.0074 (14)	0.0081 (13)	−0.0002 (13)
C10	0.0700 (19)	0.0473 (15)	0.0491 (15)	0.0006 (13)	0.0140 (13)	0.0065 (12)
C1	0.0653 (18)	0.0574 (18)	0.0588 (17)	0.0012 (15)	0.0059 (14)	0.0007 (15)
C12	0.0499 (16)	0.070 (2)	0.073 (2)	0.0056 (15)	0.0094 (14)	0.0128 (16)
C9	0.091 (2)	0.0506 (18)	0.0641 (19)	0.0028 (16)	0.0107 (17)	−0.0035 (14)
C3	0.074 (2)	0.0524 (17)	0.0633 (19)	−0.0022 (15)	−0.0017 (16)	0.0006 (15)
C8	0.095 (3)	0.0555 (18)	0.0529 (17)	−0.0155 (17)	0.0081 (16)	−0.0084 (14)
C11	0.0640 (19)	0.0597 (19)	0.0679 (19)	0.0152 (15)	0.0186 (15)	0.0139 (15)
C17	0.0597 (18)	0.076 (2)	0.0535 (16)	0.0012 (15)	−0.0025 (13)	0.0189 (15)
C16	0.0464 (15)	0.075 (2)	0.0531 (16)	0.0034 (14)	0.0027 (12)	0.0113 (14)
C4	0.0529 (17)	0.090 (2)	0.0533 (17)	0.0101 (16)	0.0006 (13)	−0.0065 (16)
C5	0.0502 (18)	0.123 (3)	0.0608 (19)	−0.0040 (19)	−0.0067 (14)	−0.012 (2)
C6	0.072 (2)	0.093 (3)	0.0528 (17)	−0.0194 (19)	0.0009 (15)	−0.0135 (17)
C21	0.086 (2)	0.076 (2)	0.0607 (19)	−0.0141 (19)	0.0153 (17)	0.0077 (17)
C22	0.115 (3)	0.098 (3)	0.073 (2)	−0.022 (3)	0.011 (2)	0.025 (2)
S1	0.068 (4)	0.061 (4)	0.069 (4)	−0.007 (2)	0.022 (3)	−0.009 (3)
O4	0.065 (6)	0.094 (10)	0.105 (15)	−0.017 (5)	0.007 (6)	0.013 (9)
O5	0.131 (14)	0.069 (8)	0.098 (12)	−0.007 (8)	0.018 (10)	−0.026 (8)
O6	0.066 (11)	0.080 (9)	0.055 (7)	0.002 (10)	0.011 (7)	0.009 (6)
C23	0.092 (8)	0.078 (7)	0.060 (7)	−0.017 (7)	0.000 (6)	0.002 (6)
F1	0.139 (14)	0.073 (6)	0.123 (12)	0.013 (6)	−0.017 (9)	−0.007 (7)
F2	0.085 (7)	0.142 (13)	0.154 (14)	−0.017 (7)	−0.015 (7)	0.021 (11)
F3	0.155 (13)	0.129 (10)	0.057 (5)	0.003 (10)	0.020 (7)	0.005 (5)
S1A	0.068 (2)	0.060 (2)	0.071 (3)	−0.0102 (18)	0.007 (2)	−0.015 (2)
O4A	0.160 (18)	0.074 (7)	0.091 (14)	−0.014 (8)	0.033 (11)	−0.027 (8)
O5A	0.094 (8)	0.123 (13)	0.089 (9)	−0.047 (8)	−0.021 (7)	−0.002 (8)
O6A	0.143 (11)	0.095 (13)	0.077 (8)	0.038 (8)	0.039 (7)	0.005 (7)
C23A	0.064 (8)	0.093 (8)	0.077 (8)	0.006 (8)	0.014 (6)	−0.009 (7)
F1A	0.091 (9)	0.113 (12)	0.077 (7)	0.008 (7)	0.021 (7)	0.002 (6)
F2A	0.077 (7)	0.187 (15)	0.102 (12)	−0.012 (8)	−0.012 (6)	0.008 (10)
F3A	0.162 (11)	0.087 (6)	0.103 (9)	0.036 (6)	0.032 (7)	0.008 (5)
S1B	0.049 (3)	0.064 (4)	0.066 (4)	−0.010 (2)	−0.003 (3)	0.004 (3)
O4B	0.039 (6)	0.113 (16)	0.069 (11)	−0.009 (7)	−0.007 (6)	0.018 (10)
O5B	0.086 (11)	0.056 (6)	0.102 (14)	−0.004 (6)	0.037 (10)	0.002 (6)
O6B	0.073 (10)	0.102 (13)	0.079 (10)	−0.030 (8)	0.025 (9)	−0.021 (9)
C23B	0.075 (9)	0.062 (7)	0.055 (8)	−0.003 (7)	−0.018 (6)	0.005 (6)
F1B	0.091 (9)	0.058 (6)	0.072 (9)	−0.009 (6)	−0.002 (6)	0.004 (5)
F2B	0.098 (9)	0.138 (13)	0.117 (12)	−0.021 (9)	−0.058 (9)	−0.002 (10)
F3B	0.140 (14)	0.080 (11)	0.075 (8)	0.005 (11)	0.027 (10)	0.011 (7)

Geometric parameters (Å, º)

Re1—C1	1.917 (3)	C11—H11	0.9300
Re1—C3	1.918 (3)	C17—C16	1.371 (4)
Re1—C2	1.923 (3)	C17—H17	0.9300
Re1—N2	2.174 (2)	C16—H16	0.9300
Re1—N1	2.185 (2)	C4—C5	1.397 (5)
Re1—N3	2.218 (2)	C4—H4	0.9300
N2—C13	1.338 (3)	C5—C6	1.358 (5)
N2—C14	1.363 (3)	C5—H5	0.9300
N1—C4	1.330 (4)	C6—H6	0.9300
N1—C15	1.369 (4)	C21—C22	1.283 (6)
O2—C2	1.144 (4)	C21—H21	0.9300
N3—C16	1.338 (4)	C22—H22A	0.9300
N3—C20	1.344 (4)	C22—H22B	0.9300
C15—C7	1.402 (4)	S1—O4	1.445 (12)
C15—C14	1.426 (4)	S1—O6	1.445 (12)
O1—C1	1.145 (4)	S1—O5	1.446 (11)
O3—C3	1.147 (4)	S1—C23	1.845 (17)
C14—C10	1.402 (4)	C23—F2	1.293 (14)
C7—C6	1.400 (5)	C23—F1	1.302 (14)
C7—C8	1.434 (5)	C23—F3	1.317 (13)
C20—C19	1.373 (4)	S1A—O5A	1.450 (12)
C20—H20	0.9300	S1A—O4A	1.456 (14)
C19—C18	1.384 (4)	S1A—O6A	1.456 (12)
C19—H19	0.9300	S1A—C23A	1.849 (18)
C13—C12	1.381 (4)	C23A—F1A	1.291 (15)
C13—H13	0.9300	C23A—F3A	1.293 (16)
C18—C17	1.379 (4)	C23A—F2A	1.298 (15)
C18—C21	1.473 (4)	S1B—O5B	1.443 (12)
C10—C11	1.403 (4)	S1B—O6B	1.446 (13)
C10—C9	1.423 (4)	S1B—O4B	1.450 (12)
C12—C11	1.350 (5)	S1B—C23B	1.85 (2)
C12—H12	0.9300	C23B—F2B	1.306 (14)
C9—C8	1.337 (5)	C23B—F3B	1.306 (15)
C9—H9	0.9300	C23B—F1B	1.313 (14)
C8—H8	0.9300
C1—Re1—C3	88.35 (14)	C12—C11—C10	119.9 (3)
C1—Re1—C2	88.70 (13)	C12—C11—H11	120.0
C3—Re1—C2	88.39 (14)	C10—C11—H11	120.0
C1—Re1—N2	91.89 (11)	C16—C17—C18	120.3 (3)
C3—Re1—N2	97.18 (12)	C16—C17—H17	119.8
C2—Re1—N2	174.41 (11)	C18—C17—H17	119.8
C1—Re1—N1	96.48 (11)	N3—C16—C17	123.9 (3)
C3—Re1—N1	171.39 (11)	N3—C16—H16	118.0
C2—Re1—N1	98.81 (11)	C17—C16—H16	118.0
N2—Re1—N1	75.59 (8)	N1—C4—C5	122.5 (3)
C1—Re1—N3	178.44 (11)	N1—C4—H4	118.7
C3—Re1—N3	92.69 (12)	C5—C4—H4	118.7
C2—Re1—N3	92.49 (11)	C6—C5—C4	119.7 (3)
N2—Re1—N3	86.83 (8)	C6—C5—H5	120.1
N1—Re1—N3	82.34 (8)	C4—C5—H5	120.1
C13—N2—C14	117.7 (2)	C5—C6—C7	120.1 (3)
C13—N2—Re1	126.9 (2)	C5—C6—H6	120.0
C14—N2—Re1	115.35 (17)	C7—C6—H6	120.0
C4—N1—C15	117.6 (3)	C22—C21—C18	125.3 (4)
C4—N1—Re1	127.8 (2)	C22—C21—H21	117.3
C15—N1—Re1	114.49 (17)	C18—C21—H21	117.3
C16—N3—C20	115.8 (2)	C21—C22—H22A	120.0
C16—N3—Re1	122.66 (18)	C21—C22—H22B	120.0
C20—N3—Re1	121.51 (19)	H22A—C22—H22B	120.0
N1—C15—C7	123.2 (3)	O4—S1—O6	115.0 (14)
N1—C15—C14	117.3 (2)	O4—S1—O5	118.1 (14)
C7—C15—C14	119.5 (3)	O6—S1—O5	115.8 (14)
N2—C14—C10	122.4 (2)	O4—S1—C23	101.6 (11)
N2—C14—C15	116.9 (2)	O6—S1—C23	102.3 (11)
C10—C14—C15	120.6 (3)	O5—S1—C23	99.9 (11)
C6—C7—C15	116.9 (3)	F2—C23—F1	107.3 (17)
C6—C7—C8	124.5 (3)	F2—C23—F3	110.7 (16)
C15—C7—C8	118.6 (3)	F1—C23—F3	108.0 (17)
O2—C2—Re1	178.9 (3)	F2—C23—S1	110.2 (15)
N3—C20—C19	123.3 (3)	F1—C23—S1	111.1 (16)
N3—C20—H20	118.4	F3—C23—S1	109.5 (13)
C19—C20—H20	118.4	O5A—S1A—O4A	117.4 (14)
C20—C19—C18	120.5 (3)	O5A—S1A—O6A	116.9 (13)
C20—C19—H19	119.7	O4A—S1A—O6A	115.3 (14)
C18—C19—H19	119.7	O5A—S1A—C23A	101.6 (9)
N2—C13—C12	122.8 (3)	O4A—S1A—C23A	100.3 (11)
N2—C13—H13	118.6	O6A—S1A—C23A	100.5 (10)
C12—C13—H13	118.6	F1A—C23A—F3A	107.7 (18)
C17—C18—C19	116.1 (3)	F1A—C23A—F2A	107.3 (19)
C17—C18—C21	122.9 (3)	F3A—C23A—F2A	105.1 (18)
C19—C18—C21	121.0 (3)	F1A—C23A—S1A	112.6 (16)
C14—C10—C11	117.2 (3)	F3A—C23A—S1A	111.5 (13)
C14—C10—C9	118.3 (3)	F2A—C23A—S1A	112.2 (16)
C11—C10—C9	124.5 (3)	O5B—S1B—O6B	117.1 (15)
O1—C1—Re1	178.6 (3)	O5B—S1B—O4B	115.8 (14)
C11—C12—C13	119.8 (3)	O6B—S1B—O4B	116.4 (15)
C11—C12—H12	120.1	O5B—S1B—C23B	101.3 (12)
C13—C12—H12	120.1	O6B—S1B—C23B	100.5 (13)
C8—C9—C10	121.6 (3)	O4B—S1B—C23B	101.3 (12)
C8—C9—H9	119.2	F2B—C23B—F3B	109.0 (18)
C10—C9—H9	119.2	F2B—C23B—F1B	106.9 (18)
O3—C3—Re1	179.3 (3)	F3B—C23B—F1B	108.1 (17)
C9—C8—C7	121.4 (3)	F2B—C23B—S1B	110.3 (15)
C9—C8—H8	119.3	F3B—C23B—S1B	110.6 (15)
C7—C8—H8	119.3	F1B—C23B—S1B	111.8 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···F2A^i	0.93	2.40	3.24 (2)	149
C20—H20···O4B^i	0.93	2.57	3.42 (2)	152
C13—H13···O6B	0.93	2.41	3.15 (3)	136
C12—H12···O5B	0.93	2.58	3.30 (2)	135
C17—H17···F3B^ii	0.93	2.56	3.42 (3)	154
C16—H16···N2	0.93	2.61	3.116 (4)	115
C16—H16···F1^ii	0.93	2.63	3.34 (3)	133
C16—H16···O4A^ii	0.93	2.58	3.23 (3)	127
C16—H16···F1B^ii	0.93	2.57	3.22 (2)	127
C4—H4···O4^i	0.93	2.44	3.19 (3)	139
C4—H4···O4B^i	0.93	2.56	3.24 (3)	130
C5—H5···O6A^i	0.93	2.59	3.27 (2)	130

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