fac-[1,2-Bis(pyridin-4-yl)ethane-κN]tricarbon-yl(1,10-phenanthroline-κ(2) N,N')rhenium(I) hexa-fluorido-phosphate aceto-nitrile monosolvate.

The asymmetric unit of the title compound, [Re(C12H8N2)(C12H12N2)(CO)3]PF6.·CH3CN, contains one cation, one hexa-fluorido-phosphate anion and one aceto-nitrile solvent mol-ecule. The Re(I) ion is coordinated by two N atoms from the 1,10-phenanthroline ligand and one N atom from the 1,2-bis-(pyridin-4-yl)ethane ligand [mean Re-N = 2.191 (15) Å] and by three carbonyl ligands [mean Re-C = 1.926 (3) Å] in a distorted octa-hedral geometry. The electrostatic forces and weak C-H⋯F(O) hydrogen bonds pack cations and anions into the crystal with voids of 82 Å(3), which are filled by solvent mol-ecules. The crystal packing exhibits short inter-molecular O⋯O distance of 2.795 (5) Å between two cations related by inversion.

Related literature

For photophysical and photochemical properties of rhenium(I)–polypyridyl complexes, see: Li et al. (2012 ▶); Mizoguchi et al. (2009 ▶); Patrocinio et al. (2010 ▶, 2013 ▶); Thorp-Greenwood et al. (2012 ▶). For similar compounds and their crystal structures, see: Ranjan et al. (2003 ▶); Wenger et al. (2004 ▶); Ide et al. (1995 ▶). For details of the synthetic procedure, see: Patrocinio et al. (2010 ▶); Patrocinio & Murakami Iha (2008 ▶); Argazzi et al. (2001 ▶).

Experimental

Crystal data

[Re(C12H8N2)(C12H12N2)(CO)3]PF6·C2H3N

M = 820.69

Monoclinic,

a = 10.5992 (2) Å

b = 16.1201 (3) Å

c = 17.3449 (2) Å

β = 100.879 (1)°

V = 2910.29 (8) Å3

Z = 4

Mo Kα radiation

μ = 4.31 mm−1

T = 100 K

0.29 × 0.20 × 0.13 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: Gaussian (Coppen et al., 1965 ▶) T min = 0.386, T max = 0.613

35034 measured reflections

6066 independent reflections

5415 reflections with I > 2σ(I)

R int = 0.106

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.109

S = 1.09

6066 reflections

406 parameters

H-atom parameters constrained

Δρmax = 1.39 e Å−3

Δρmin = −2.50 e Å−3

Data collection: COLLECT (Hooft, 2004 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814014135/cv5465sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814014135/cv5465Isup2.hkl

CCDC reference: 1008626

Additional supporting information: crystallographic information; 3D view; checkCIF report

[Re(C12H8N2)(C12H12N2)(CO)3]PF6·C2H3N	F(000) = 1600
Mr = 820.69	Dx = 1.873 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.5992 (2) Å	Cell parameters from 20552 reflections
b = 16.1201 (3) Å	θ = 2.9–26.7°
c = 17.3449 (2) Å	µ = 4.31 mm−1
β = 100.879 (1)°	T = 100 K
V = 2910.29 (8) Å3	Prism, colourless
Z = 4	0.29 × 0.20 × 0.13 mm

Nonius KappaCCD diffractometer	6066 independent reflections
Radiation source: Enraf–Nonius FR590	5415 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.106
Detector resolution: 9 pixels mm-1	θmax = 26.6°, θmin = 3.1°
CCD rotation images, thick slices scans	h = −13→13
Absorption correction: gaussian (Coppens et al., 1965)	k = −18→20
Tmin = 0.386, Tmax = 0.613	l = −21→21
35034 measured reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0541P)2 + 8.7438P] where P = (Fo2 + 2Fc2)/3
6066 reflections	(Δ/σ)max = 0.002
406 parameters	Δρmax = 1.39 e Å−3
0 restraints	Δρmin = −2.50 e Å−3

Experimental. a grid of 8 x 8 x 8 = 512 sampling points was used in the absorption correction

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
Re	0.804584 (18)	0.150099 (11)	0.635436 (10)	0.01716 (9)
O1	0.5921 (4)	0.0300 (3)	0.5622 (2)	0.0328 (9)
O2	0.9983 (4)	0.0058 (2)	0.6471 (2)	0.0302 (9)
O3	0.8369 (4)	0.1791 (3)	0.46486 (19)	0.0268 (8)
N1	0.7658 (4)	0.1315 (3)	0.7536 (2)	0.0199 (9)
N2	0.6642 (4)	0.2458 (3)	0.6470 (2)	0.0193 (8)
N3	0.9448 (4)	0.2463 (3)	0.6853 (2)	0.0196 (8)
N4	1.3479 (5)	0.6998 (3)	0.9550 (3)	0.0292 (10)
N5	0.7950 (6)	0.3895 (4)	0.8097 (4)	0.0460 (14)
C1	0.6701 (5)	0.0737 (3)	0.5915 (3)	0.0225 (11)
C2	0.9281 (5)	0.0614 (3)	0.6420 (3)	0.0234 (11)
C3	0.8273 (5)	0.1710 (3)	0.5297 (3)	0.0244 (11)
C4	0.8152 (5)	0.0726 (3)	0.8044 (3)	0.0237 (11)
H4	0.8778	0.0375	0.7916	0.028*
C5	0.7759 (6)	0.0619 (4)	0.8764 (3)	0.0304 (12)
H5	0.8109	0.0193	0.9099	0.036*
C6	0.6858 (6)	0.1141 (4)	0.8979 (3)	0.0278 (12)
H6	0.6604	0.108	0.946	0.033*
C7	0.6330 (5)	0.1772 (3)	0.8453 (3)	0.0221 (10)
C8	0.5392 (5)	0.2344 (3)	0.8619 (3)	0.0228 (10)
H8	0.5104	0.2306	0.9092	0.027*
C9	0.4913 (5)	0.2947 (3)	0.8094 (3)	0.0228 (10)
H9	0.4314	0.3322	0.8219	0.027*
C10	0.5316 (5)	0.3013 (3)	0.7355 (3)	0.0206 (10)
C11	0.4825 (6)	0.3620 (3)	0.6783 (3)	0.0255 (12)
H11	0.4231	0.4012	0.6881	0.031*
C12	0.5247 (6)	0.3614 (3)	0.6080 (3)	0.0260 (12)
H12	0.4927	0.4001	0.5695	0.031*
C13	0.6158 (5)	0.3028 (3)	0.5941 (3)	0.0215 (10)
H13	0.6433	0.3039	0.5463	0.026*
C14	0.6757 (5)	0.1834 (3)	0.7736 (3)	0.0182 (9)
C15	0.6230 (5)	0.2453 (3)	0.7174 (3)	0.0189 (10)
C16	0.9463 (5)	0.3204 (3)	0.6488 (3)	0.0225 (10)
H16	0.8911	0.3283	0.6009	0.027*
C17	1.0259 (5)	0.3845 (3)	0.6794 (3)	0.0241 (11)
H17	1.0224	0.4346	0.6526	0.029*
C18	1.1111 (5)	0.3747 (3)	0.7497 (3)	0.0222 (10)
C19	1.1136 (5)	0.2970 (3)	0.7860 (3)	0.0229 (11)
H19	1.1716	0.2868	0.8324	0.027*
C20	1.0294 (5)	0.2353 (3)	0.7528 (3)	0.0212 (10)
H20	1.0316	0.1844	0.7781	0.025*
C21	1.1946 (5)	0.4445 (3)	0.7878 (3)	0.0237 (10)
H21A	1.2319	0.4734	0.7484	0.028*
H21B	1.2641	0.4223	0.8268	0.028*
C22	1.1154 (6)	0.5050 (4)	0.8268 (4)	0.0398 (15)
H22A	1.0503	0.5301	0.7868	0.048*
H22B	1.072	0.4747	0.8624	0.048*
C23	1.1966 (5)	0.5727 (4)	0.8718 (3)	0.0286 (13)
C24	1.1984 (6)	0.6522 (3)	0.8408 (4)	0.0302 (13)
H24	1.1498	0.6645	0.7917	0.036*
C25	1.2736 (6)	0.7129 (3)	0.8839 (3)	0.0276 (12)
H25	1.2727	0.7658	0.8624	0.033*
C26	1.3481 (6)	0.6218 (4)	0.9832 (3)	0.0323 (13)
H26	1.3998	0.6103	1.0315	0.039*
C27	1.2757 (6)	0.5582 (4)	0.9441 (3)	0.0339 (13)
H27	1.2798	0.5055	0.9662	0.041*
C28	0.8459 (7)	0.3541 (4)	0.8642 (4)	0.0392 (16)
C29	0.9137 (7)	0.3104 (5)	0.9339 (4)	0.0464 (16)
H29A	0.9862	0.2814	0.9212	0.07*
H29B	0.8565	0.2714	0.9513	0.07*
H29C	0.9427	0.3498	0.975	0.07*
P	0.72529 (14)	0.43615 (8)	0.41578 (7)	0.0227 (3)
F1	0.6050 (3)	0.4560 (2)	0.45748 (19)	0.0332 (7)
F2	0.7573 (3)	0.53361 (19)	0.41536 (18)	0.0299 (7)
F3	0.8432 (4)	0.4168 (2)	0.3742 (2)	0.0422 (9)
F4	0.6912 (4)	0.33928 (19)	0.4165 (2)	0.0399 (9)
F5	0.6330 (3)	0.44566 (19)	0.33112 (17)	0.0294 (7)
F6	0.8144 (4)	0.4265 (2)	0.50075 (19)	0.0373 (8)

	U11	U22	U33	U12	U13	U23
Re	0.01953 (14)	0.01844 (14)	0.01390 (12)	0.00022 (7)	0.00417 (8)	0.00007 (6)
O1	0.033 (2)	0.034 (2)	0.031 (2)	−0.0109 (18)	0.0033 (17)	−0.0095 (17)
O2	0.031 (2)	0.027 (2)	0.033 (2)	0.0107 (17)	0.0089 (17)	0.0046 (16)
O3	0.033 (2)	0.037 (2)	0.0114 (17)	−0.0021 (18)	0.0074 (14)	0.0034 (15)
N1	0.028 (2)	0.023 (2)	0.0108 (18)	0.0000 (18)	0.0081 (16)	0.0028 (16)
N2	0.024 (2)	0.017 (2)	0.0179 (19)	0.0026 (16)	0.0055 (16)	0.0011 (16)
N3	0.019 (2)	0.021 (2)	0.0177 (19)	−0.0012 (17)	0.0015 (16)	0.0001 (16)
N4	0.036 (3)	0.024 (2)	0.026 (2)	−0.003 (2)	0.0039 (19)	−0.0001 (19)
N5	0.043 (3)	0.043 (3)	0.049 (3)	−0.006 (3)	0.001 (3)	−0.008 (3)
C1	0.021 (3)	0.030 (3)	0.018 (2)	0.002 (2)	0.0066 (19)	−0.001 (2)
C2	0.027 (3)	0.027 (3)	0.017 (2)	−0.005 (2)	0.007 (2)	0.002 (2)
C3	0.018 (3)	0.019 (2)	0.034 (3)	−0.001 (2)	0.002 (2)	−0.001 (2)
C4	0.025 (3)	0.025 (3)	0.023 (2)	0.004 (2)	0.011 (2)	0.010 (2)
C5	0.046 (4)	0.027 (3)	0.020 (2)	0.009 (2)	0.009 (2)	0.007 (2)
C6	0.030 (3)	0.036 (3)	0.018 (2)	0.003 (2)	0.008 (2)	0.002 (2)
C7	0.021 (3)	0.028 (3)	0.017 (2)	−0.004 (2)	0.0031 (19)	−0.004 (2)
C8	0.026 (3)	0.026 (3)	0.018 (2)	−0.002 (2)	0.0067 (19)	−0.003 (2)
C9	0.022 (3)	0.026 (3)	0.022 (2)	0.000 (2)	0.008 (2)	−0.005 (2)
C10	0.022 (3)	0.016 (2)	0.024 (2)	−0.0013 (19)	0.0051 (19)	−0.0038 (19)
C11	0.028 (3)	0.027 (3)	0.021 (3)	0.007 (2)	0.002 (2)	−0.002 (2)
C12	0.024 (3)	0.025 (3)	0.028 (3)	0.002 (2)	0.003 (2)	0.007 (2)
C13	0.022 (3)	0.024 (3)	0.019 (2)	0.000 (2)	0.0039 (19)	0.005 (2)
C14	0.018 (2)	0.020 (2)	0.016 (2)	−0.0026 (19)	0.0016 (18)	−0.0006 (18)
C15	0.019 (2)	0.020 (2)	0.018 (2)	−0.0019 (19)	0.0054 (18)	−0.0004 (19)
C16	0.026 (3)	0.024 (3)	0.017 (2)	0.000 (2)	0.0020 (19)	0.003 (2)
C17	0.028 (3)	0.020 (3)	0.024 (3)	0.000 (2)	0.006 (2)	0.005 (2)
C18	0.021 (3)	0.021 (3)	0.026 (3)	0.001 (2)	0.009 (2)	−0.001 (2)
C19	0.023 (3)	0.027 (3)	0.017 (2)	−0.001 (2)	0.0006 (19)	0.002 (2)
C20	0.027 (3)	0.020 (2)	0.017 (2)	−0.001 (2)	0.0037 (19)	0.0004 (19)
C21	0.028 (3)	0.024 (3)	0.020 (2)	−0.003 (2)	0.006 (2)	−0.001 (2)
C22	0.025 (3)	0.034 (3)	0.061 (4)	−0.003 (3)	0.010 (3)	−0.019 (3)
C23	0.022 (3)	0.027 (3)	0.039 (3)	−0.004 (2)	0.012 (2)	−0.012 (2)
C24	0.031 (3)	0.032 (3)	0.026 (3)	0.007 (2)	0.000 (2)	−0.004 (2)
C25	0.031 (3)	0.023 (3)	0.029 (3)	0.000 (2)	0.005 (2)	0.000 (2)
C26	0.042 (4)	0.031 (3)	0.024 (3)	−0.001 (3)	0.007 (2)	0.002 (2)
C27	0.049 (4)	0.023 (3)	0.033 (3)	−0.002 (3)	0.018 (3)	0.006 (2)
C28	0.036 (4)	0.036 (4)	0.045 (4)	−0.009 (3)	0.007 (3)	−0.013 (3)
C29	0.045 (4)	0.048 (4)	0.045 (4)	−0.005 (3)	0.006 (3)	−0.005 (3)
P	0.0310 (8)	0.0219 (7)	0.0153 (6)	0.0034 (5)	0.0046 (5)	0.0005 (5)
F1	0.0371 (19)	0.0351 (18)	0.0312 (16)	0.0021 (15)	0.0162 (14)	−0.0018 (14)
F2	0.0366 (19)	0.0246 (17)	0.0267 (15)	−0.0045 (13)	0.0013 (13)	0.0017 (13)
F3	0.048 (2)	0.048 (2)	0.0354 (18)	0.0192 (18)	0.0200 (16)	0.0068 (16)
F4	0.075 (3)	0.0202 (17)	0.0249 (17)	0.0009 (16)	0.0113 (18)	−0.0003 (13)
F5	0.0396 (19)	0.0265 (16)	0.0184 (14)	−0.0059 (14)	−0.0035 (13)	0.0014 (12)
F6	0.045 (2)	0.040 (2)	0.0226 (16)	0.0098 (16)	−0.0042 (14)	0.0071 (14)

Re—C1	1.929 (5)	C13—H13	0.93
Re—C2	1.927 (6)	C14—C15	1.432 (7)
Re—C3	1.923 (6)	C16—C17	1.375 (8)
Re—N1	2.186 (4)	C16—H16	0.93
Re—N2	2.179 (4)	C17—C18	1.384 (7)
Re—N3	2.208 (4)	C17—H17	0.93
O1—C1	1.131 (7)	C18—C19	1.399 (7)
O2—C2	1.158 (7)	C18—C21	1.504 (7)
O3—C3	1.156 (7)	C19—C20	1.387 (7)
N1—C4	1.334 (6)	C19—H19	0.93
N1—C14	1.363 (7)	C20—H20	0.93
N2—C13	1.330 (6)	C21—C22	1.526 (8)
N2—C15	1.372 (6)	C21—H21A	0.97
N3—C20	1.346 (6)	C21—H21B	0.97
N3—C16	1.353 (7)	C22—C23	1.513 (8)
N4—C25	1.348 (7)	C22—H22A	0.97
N4—C26	1.349 (8)	C22—H22B	0.97
N5—C28	1.148 (9)	C23—C27	1.390 (8)
C4—C5	1.400 (7)	C23—C24	1.391 (8)
C4—H4	0.93	C24—C25	1.388 (8)
C5—C6	1.376 (8)	C24—H24	0.93
C5—H5	0.93	C25—H25	0.93
C6—C7	1.410 (8)	C26—C27	1.379 (9)
C6—H6	0.93	C26—H26	0.93
C7—C14	1.405 (7)	C27—H27	0.93
C7—C8	1.425 (7)	C28—C29	1.466 (10)
C8—C9	1.363 (7)	C29—H29A	0.96
C8—H8	0.93	C29—H29B	0.96
C9—C10	1.431 (7)	C29—H29C	0.96
C9—H9	0.93	P—F3	1.587 (4)
C10—C15	1.403 (7)	P—F6	1.601 (3)
C10—C11	1.420 (7)	P—F4	1.603 (3)
C11—C12	1.375 (8)	P—F2	1.608 (3)
C11—H11	0.93	P—F5	1.611 (3)
C12—C13	1.404 (8)	P—F1	1.612 (3)
C12—H12	0.93
C3—Re—C2	88.9 (2)	N3—C16—C17	122.9 (5)
C3—Re—C1	87.2 (2)	N3—C16—H16	118.6
C2—Re—C1	89.6 (2)	C17—C16—H16	118.6
C3—Re—N2	100.01 (19)	C16—C17—C18	120.4 (5)
C2—Re—N2	171.09 (18)	C16—C17—H17	119.8
C1—Re—N2	91.25 (19)	C18—C17—H17	119.8
C3—Re—N1	175.83 (19)	C17—C18—C19	116.9 (5)
C2—Re—N1	95.09 (19)	C17—C18—C21	122.2 (5)
C1—Re—N1	91.52 (19)	C19—C18—C21	120.9 (5)
N2—Re—N1	76.02 (16)	C20—C19—C18	119.9 (5)
C3—Re—N3	93.08 (19)	C20—C19—H19	120
C2—Re—N3	95.64 (19)	C18—C19—H19	120
C1—Re—N3	174.74 (19)	N3—C20—C19	122.6 (5)
N2—Re—N3	83.52 (16)	N3—C20—H20	118.7
N1—Re—N3	87.78 (16)	C19—C20—H20	118.7
C4—N1—C14	118.4 (4)	C18—C21—C22	110.2 (5)
C4—N1—Re	126.7 (4)	C18—C21—H21A	109.6
C14—N1—Re	114.8 (3)	C22—C21—H21A	109.6
C13—N2—C15	118.2 (4)	C18—C21—H21B	109.6
C13—N2—Re	127.4 (3)	C22—C21—H21B	109.6
C15—N2—Re	114.5 (3)	H21A—C21—H21B	108.1
C20—N3—C16	117.3 (4)	C23—C22—C21	112.6 (5)
C20—N3—Re	122.5 (3)	C23—C22—H22A	109.1
C16—N3—Re	120.2 (3)	C21—C22—H22A	109.1
C25—N4—C26	116.0 (5)	C23—C22—H22B	109.1
O1—C1—Re	176.6 (5)	C21—C22—H22B	109.1
O2—C2—Re	176.9 (5)	H22A—C22—H22B	107.8
O3—C3—Re	175.7 (5)	C27—C23—C24	117.0 (5)
N1—C4—C5	122.1 (5)	C27—C23—C22	122.1 (6)
N1—C4—H4	119	C24—C23—C22	120.8 (6)
C5—C4—H4	119	C25—C24—C23	119.3 (5)
C6—C5—C4	120.3 (5)	C25—C24—H24	120.4
C6—C5—H5	119.8	C23—C24—H24	120.4
C4—C5—H5	119.8	N4—C25—C24	124.0 (5)
C5—C6—C7	118.6 (5)	N4—C25—H25	118
C5—C6—H6	120.7	C24—C25—H25	118
C7—C6—H6	120.7	N4—C26—C27	123.5 (5)
C14—C7—C6	117.9 (5)	N4—C26—H26	118.3
C14—C7—C8	119.2 (5)	C27—C26—H26	118.3
C6—C7—C8	122.9 (5)	C26—C27—C23	120.2 (5)
C9—C8—C7	120.8 (5)	C26—C27—H27	119.9
C9—C8—H8	119.6	C23—C27—H27	119.9
C7—C8—H8	119.6	N5—C28—C29	178.5 (8)
C8—C9—C10	121.0 (5)	C28—C29—H29A	109.5
C8—C9—H9	119.5	C28—C29—H29B	109.5
C10—C9—H9	119.5	H29A—C29—H29B	109.5
C15—C10—C11	117.7 (5)	C28—C29—H29C	109.5
C15—C10—C9	119.2 (5)	H29A—C29—H29C	109.5
C11—C10—C9	123.0 (5)	H29B—C29—H29C	109.5
C12—C11—C10	118.5 (5)	F3—P—F6	91.2 (2)
C12—C11—H11	120.7	F3—P—F4	90.6 (2)
C10—C11—H11	120.7	F6—P—F4	89.6 (2)
C11—C12—C13	120.4 (5)	F3—P—F2	90.3 (2)
C11—C12—H12	119.8	F6—P—F2	90.64 (18)
C13—C12—H12	119.8	F4—P—F2	179.1 (2)
N2—C13—C12	122.3 (5)	F3—P—F5	89.95 (19)
N2—C13—H13	118.8	F6—P—F5	178.8 (2)
C12—C13—H13	118.8	F4—P—F5	90.05 (19)
N1—C14—C7	122.7 (5)	F2—P—F5	89.73 (17)
N1—C14—C15	117.1 (4)	F3—P—F1	179.6 (2)
C7—C14—C15	120.1 (5)	F6—P—F1	89.17 (19)
N2—C15—C10	122.9 (4)	F4—P—F1	89.5 (2)
N2—C15—C14	117.5 (4)	F2—P—F1	89.67 (18)
C10—C15—C14	119.5 (4)	F5—P—F1	89.68 (19)
C2—Re—N1—C4	−2.6 (5)	Re—N1—C14—C7	176.1 (4)
C1—Re—N1—C4	87.1 (5)	C4—N1—C14—C15	−179.1 (5)
N2—Re—N1—C4	178.0 (5)	Re—N1—C14—C15	−2.9 (6)
N3—Re—N1—C4	−98.1 (5)	C6—C7—C14—N1	−0.3 (8)
C2—Re—N1—C14	−178.5 (4)	C8—C7—C14—N1	179.5 (5)
C1—Re—N1—C14	−88.8 (4)	C6—C7—C14—C15	178.6 (5)
N2—Re—N1—C14	2.1 (3)	C8—C7—C14—C15	−1.6 (7)
N3—Re—N1—C14	86.0 (4)	C13—N2—C15—C10	0.7 (7)
C3—Re—N2—C13	−2.3 (5)	Re—N2—C15—C10	−179.1 (4)
C1—Re—N2—C13	−89.7 (5)	C13—N2—C15—C14	179.9 (4)
N1—Re—N2—C13	179.1 (5)	Re—N2—C15—C14	0.0 (6)
N3—Re—N2—C13	89.7 (4)	C11—C10—C15—N2	−1.3 (7)
C3—Re—N2—C15	177.6 (4)	C9—C10—C15—N2	178.2 (5)
C1—Re—N2—C15	90.1 (4)	C11—C10—C15—C14	179.6 (5)
N1—Re—N2—C15	−1.1 (3)	C9—C10—C15—C14	−1.0 (7)
N3—Re—N2—C15	−90.4 (3)	N1—C14—C15—N2	1.9 (7)
C3—Re—N3—C20	−139.5 (4)	C7—C14—C15—N2	−177.1 (5)
C2—Re—N3—C20	−50.3 (4)	N1—C14—C15—C10	−178.9 (5)
N2—Re—N3—C20	120.7 (4)	C7—C14—C15—C10	2.1 (7)
N1—Re—N3—C20	44.6 (4)	C20—N3—C16—C17	−2.7 (8)
C3—Re—N3—C16	41.9 (4)	Re—N3—C16—C17	176.0 (4)
C2—Re—N3—C16	131.1 (4)	N3—C16—C17—C18	1.2 (8)
N2—Re—N3—C16	−57.9 (4)	C16—C17—C18—C19	1.5 (8)
N1—Re—N3—C16	−134.0 (4)	C16—C17—C18—C21	−176.4 (5)
C14—N1—C4—C5	1.1 (8)	C17—C18—C19—C20	−2.5 (8)
Re—N1—C4—C5	−174.7 (4)	C21—C18—C19—C20	175.4 (5)
N1—C4—C5—C6	−1.6 (9)	C16—N3—C20—C19	1.6 (8)
C4—C5—C6—C7	1.1 (9)	Re—N3—C20—C19	−177.0 (4)
C5—C6—C7—C14	−0.2 (8)	C18—C19—C20—N3	1.0 (8)
C5—C6—C7—C8	−180.0 (5)	C17—C18—C21—C22	76.3 (7)
C14—C7—C8—C9	−0.1 (8)	C19—C18—C21—C22	−101.5 (6)
C6—C7—C8—C9	179.6 (5)	C18—C21—C22—C23	175.2 (5)
C7—C8—C9—C10	1.3 (8)	C21—C22—C23—C27	−75.2 (8)
C8—C9—C10—C15	−0.7 (8)	C21—C22—C23—C24	102.5 (7)
C8—C9—C10—C11	178.7 (5)	C27—C23—C24—C25	−2.5 (9)
C15—C10—C11—C12	1.4 (8)	C22—C23—C24—C25	179.7 (6)
C9—C10—C11—C12	−178.0 (5)	C26—N4—C25—C24	1.1 (9)
C10—C11—C12—C13	−1.0 (8)	C23—C24—C25—N4	0.8 (10)
C15—N2—C13—C12	−0.2 (8)	C25—N4—C26—C27	−1.4 (9)
Re—N2—C13—C12	179.6 (4)	N4—C26—C27—C23	−0.3 (10)
C11—C12—C13—N2	0.4 (8)	C24—C23—C27—C26	2.2 (9)
C4—N1—C14—C7	−0.1 (7)	C22—C23—C27—C26	−180.0 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···F4	0.93	2.47	3.377 (6)	166
C16—H16···F6	0.93	2.38	3.180 (6)	145
C11—H11···F5i	0.93	2.55	3.327 (6)	142
C12—H12···F1i	0.93	2.55	3.355 (6)	145
C5—H5···F1ii	0.93	2.52	3.382 (6)	154
C19—H19···F4iii	0.93	2.49	3.150 (6)	128
C20—H20···F5iii	0.93	2.45	3.317 (6)	154
C21—H21A···F5iv	0.97	2.53	3.486 (6)	168
C22—H22B···O1v	0.97	2.53	3.211 (8)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯F4	0.93	2.47	3.377 (6)	166
C16—H16⋯F6	0.93	2.38	3.180 (6)	145
C11—H11⋯F5i	0.93	2.55	3.327 (6)	142
C12—H12⋯F1i	0.93	2.55	3.355 (6)	145
C5—H5⋯F1ii	0.93	2.52	3.382 (6)	154
C19—H19⋯F4iii	0.93	2.49	3.150 (6)	128
C20—H20⋯F5iii	0.93	2.45	3.317 (6)	154
C21—H21A⋯F5iv	0.97	2.53	3.486 (6)	168
C22—H22B⋯O1v	0.97	2.53	3.211 (8)	127

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