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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 ReI 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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229617014644/ov3097sup1.cif
Contains datablocks 1, 2, 3, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617014644/ov30971sup2.hkl
Contains datablock 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617014644/ov30972sup3.hkl
Contains datablock 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229617014644/ov30973sup4.hkl
Contains datablock 3

CCDC references: 1564139; 1564138; 1564137

Computing details top

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) top
Crystal data top
[Re(C7H7N)(C12H8N2S)(CO)3](CF3SO3)·CH2Cl2Z = 2
Mr = 821.62F(000) = 796
Triclinic, P1Dx = 1.928 Mg m3
a = 8.596 ÅMo Kα radiation, λ = 0.71073 Å
b = 11.217 ÅCell parameters from 9893 reflections
c = 15.161 Åθ = 2.2–28.9°
α = 92.88°µ = 4.70 mm1
β = 104.12°T = 293 K
γ = 91.19°Yellow, block
V = 1415.1 Å30.20 × 0.18 × 0.15 mm
Data collection top
Bruker APEXII
diffractometer
5706 independent reflections
Radiation source: fine-focus sealed tube5462 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
Detector resolution: 8.33 pixels mm-1θmax = 26.4°, θmin = 2.2°
ω–scansh = 1010
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
k = 1414
Tmin = 0.635, Tmax = 0.746l = 1818
13569 measured reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.020Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.051H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.028P)2 + 1.0417P]
where P = (Fo2 + 2Fc2)/3
5706 reflections(Δ/σ)max = 0.003
370 parametersΔρmax = 0.91 e Å3
0 restraintsΔρmin = 0.73 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
Re10.37292 (2)0.17999 (2)0.65195 (2)0.03390 (5)
S10.91621 (9)0.27277 (8)0.75416 (6)0.04765 (18)
S20.22083 (10)0.78971 (7)0.88275 (6)0.04771 (18)
Cl10.74059 (15)0.33457 (11)0.33575 (8)0.0802 (3)
Cl20.7749 (3)0.19678 (14)0.49609 (10)0.1200 (6)
N20.6108 (3)0.2687 (2)0.68311 (16)0.0345 (5)
N10.5393 (3)0.0481 (2)0.71952 (16)0.0355 (5)
N30.3615 (3)0.2478 (2)0.78933 (17)0.0375 (5)
O30.0641 (3)0.0274 (2)0.6296 (2)0.0664 (7)
O20.1593 (3)0.3798 (2)0.5672 (2)0.0696 (8)
O10.3678 (4)0.0924 (3)0.45629 (18)0.0756 (8)
F30.2736 (4)0.7717 (3)1.05892 (17)0.1007 (9)
O40.0894 (4)0.7052 (3)0.8681 (2)0.0722 (8)
C90.7293 (3)0.2031 (3)0.72362 (18)0.0360 (6)
C80.6983 (3)0.0808 (3)0.74174 (18)0.0359 (6)
O50.3729 (4)0.7382 (3)0.8888 (2)0.0835 (9)
O60.1888 (4)0.8922 (3)0.8294 (2)0.0755 (8)
C150.6678 (4)0.3837 (3)0.6717 (2)0.0382 (6)
F20.3448 (4)0.9374 (3)1.0232 (2)0.1087 (11)
F10.0976 (4)0.8966 (4)1.0041 (2)0.1292 (14)
C30.1794 (4)0.0841 (3)0.6381 (2)0.0448 (7)
C20.2411 (4)0.3045 (3)0.5991 (2)0.0458 (7)
C100.8327 (4)0.4019 (3)0.7080 (2)0.0416 (6)
C70.8156 (4)0.0027 (3)0.7783 (2)0.0449 (7)
H70.9233860.0268680.7917050.054*
C40.4982 (4)0.0625 (3)0.7373 (2)0.0439 (7)
H40.3901240.0857790.7234940.053*
C50.6111 (4)0.1431 (3)0.7755 (2)0.0502 (8)
H50.5785600.2186160.7881680.060*
C140.5785 (4)0.4756 (3)0.6304 (3)0.0512 (8)
H140.4687830.4647730.6051680.061*
C10.3755 (4)0.1233 (3)0.5305 (2)0.0482 (7)
C200.3243 (4)0.1756 (3)0.8500 (2)0.0448 (7)
H200.3233960.0934760.8379320.054*
C60.7717 (4)0.1113 (3)0.7948 (2)0.0500 (8)
H60.8490580.1656330.8185540.060*
C120.8187 (5)0.6011 (3)0.6659 (3)0.0612 (9)
H120.8671950.6755820.6643330.073*
C180.2872 (4)0.3379 (3)0.9504 (2)0.0536 (8)
C170.3301 (5)0.4135 (3)0.8890 (3)0.0584 (9)
H170.3337620.4958860.9004430.070*
C190.2876 (4)0.2176 (3)0.9289 (2)0.0524 (8)
H190.2626150.1636120.9684070.063*
C160.3666 (4)0.3658 (3)0.8118 (2)0.0493 (8)
H160.3967480.4178580.7725870.059*
C130.6557 (5)0.5841 (3)0.6276 (3)0.0592 (9)
H130.5974220.6466360.5994940.071*
C230.2343 (5)0.8518 (4)0.9978 (3)0.0669 (10)
C110.9094 (4)0.5116 (3)0.7059 (3)0.0547 (8)
H111.0190580.5233830.7309370.066*
C210.2365 (6)0.3814 (4)1.0324 (3)0.0800 (13)
H210.2177680.3239871.0711530.096*
C220.2166 (10)0.4861 (6)1.0545 (4)0.138 (3)
H22A0.2338670.5467031.0180180.166*
H22B0.1843790.5044491.1077440.166*
C240.7974 (8)0.3360 (6)0.4520 (4)0.122 (2)
H24A0.7341010.3933040.4767860.146*
H24B0.9090180.3628950.4721350.146*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Re10.02883 (7)0.03518 (7)0.03663 (7)0.00215 (4)0.00632 (4)0.00003 (4)
S10.0313 (4)0.0522 (5)0.0567 (5)0.0028 (3)0.0055 (3)0.0052 (4)
S20.0467 (4)0.0475 (4)0.0498 (4)0.0058 (3)0.0127 (3)0.0057 (3)
Cl10.0845 (8)0.0789 (7)0.0795 (7)0.0188 (6)0.0284 (6)0.0051 (6)
Cl20.2033 (19)0.0861 (9)0.0820 (9)0.0046 (10)0.0569 (11)0.0045 (7)
N20.0312 (12)0.0355 (12)0.0371 (12)0.0004 (9)0.0089 (9)0.0011 (9)
N10.0341 (12)0.0339 (12)0.0387 (12)0.0041 (9)0.0092 (10)0.0002 (10)
N30.0343 (12)0.0358 (12)0.0424 (13)0.0032 (10)0.0097 (10)0.0002 (10)
O30.0432 (14)0.0664 (16)0.0870 (19)0.0157 (12)0.0131 (13)0.0013 (14)
O20.0522 (15)0.0551 (15)0.091 (2)0.0124 (12)0.0062 (14)0.0164 (14)
O10.093 (2)0.090 (2)0.0424 (14)0.0082 (17)0.0171 (14)0.0094 (13)
F30.145 (3)0.099 (2)0.0567 (15)0.0050 (19)0.0200 (16)0.0133 (14)
O40.0727 (19)0.0622 (17)0.0759 (18)0.0162 (14)0.0097 (15)0.0017 (14)
C90.0317 (14)0.0417 (15)0.0341 (14)0.0004 (11)0.0082 (11)0.0011 (11)
C80.0325 (14)0.0414 (15)0.0346 (14)0.0025 (11)0.0101 (11)0.0008 (11)
O50.0670 (19)0.102 (2)0.087 (2)0.0323 (17)0.0270 (16)0.0107 (18)
O60.083 (2)0.0674 (18)0.0776 (19)0.0075 (15)0.0170 (16)0.0290 (15)
C150.0378 (15)0.0397 (15)0.0394 (15)0.0012 (12)0.0148 (12)0.0004 (12)
F20.122 (3)0.0708 (17)0.108 (2)0.0196 (17)0.0141 (19)0.0198 (15)
F10.105 (2)0.178 (4)0.104 (2)0.057 (2)0.0297 (19)0.044 (2)
C30.0385 (17)0.0475 (17)0.0465 (17)0.0035 (14)0.0073 (13)0.0002 (13)
C20.0348 (16)0.0471 (17)0.0505 (18)0.0008 (13)0.0009 (13)0.0029 (14)
C100.0388 (16)0.0441 (16)0.0432 (16)0.0037 (12)0.0141 (13)0.0021 (13)
C70.0351 (16)0.0512 (18)0.0485 (17)0.0080 (13)0.0095 (13)0.0064 (14)
C40.0410 (17)0.0382 (16)0.0531 (18)0.0001 (13)0.0132 (14)0.0000 (13)
C50.055 (2)0.0360 (16)0.061 (2)0.0048 (14)0.0156 (16)0.0081 (14)
C140.0427 (18)0.0447 (17)0.068 (2)0.0018 (14)0.0155 (16)0.0078 (15)
C10.0459 (18)0.0541 (19)0.0436 (18)0.0051 (14)0.0089 (14)0.0012 (14)
C200.0476 (18)0.0407 (16)0.0467 (17)0.0086 (13)0.0115 (14)0.0052 (13)
C60.0481 (19)0.0465 (18)0.0561 (19)0.0144 (14)0.0112 (15)0.0105 (14)
C120.064 (2)0.0451 (19)0.080 (3)0.0118 (17)0.030 (2)0.0011 (17)
C180.058 (2)0.062 (2)0.0410 (17)0.0162 (17)0.0118 (15)0.0019 (15)
C170.070 (2)0.0442 (18)0.060 (2)0.0056 (16)0.0160 (18)0.0093 (16)
C190.061 (2)0.056 (2)0.0453 (18)0.0143 (16)0.0182 (15)0.0125 (15)
C160.058 (2)0.0405 (17)0.0521 (18)0.0011 (14)0.0202 (15)0.0009 (14)
C130.062 (2)0.0415 (18)0.080 (3)0.0027 (16)0.0270 (19)0.0141 (17)
C230.069 (3)0.063 (2)0.064 (2)0.008 (2)0.009 (2)0.0054 (19)
C110.0492 (19)0.0511 (19)0.066 (2)0.0125 (15)0.0207 (16)0.0032 (16)
C210.110 (4)0.077 (3)0.061 (2)0.027 (3)0.034 (2)0.002 (2)
C220.242 (9)0.098 (4)0.105 (5)0.026 (5)0.104 (6)0.012 (4)
C240.098 (4)0.119 (5)0.114 (5)0.009 (4)0.034 (4)0.003 (4)
Geometric parameters (Å, º) top
Re1—C21.900 (3)C10—C111.390 (4)
Re1—C11.923 (3)C7—C61.379 (5)
Re1—C31.924 (3)C7—H70.9300
Re1—N22.189 (2)C4—C51.381 (4)
Re1—N12.193 (2)C4—H40.9300
Re1—N32.207 (2)C5—C61.375 (5)
S1—C91.719 (3)C5—H50.9300
S1—C101.733 (3)C14—C131.382 (5)
S2—O51.424 (3)C14—H140.9300
S2—O41.427 (3)C20—C191.373 (5)
S2—O61.432 (3)C20—H200.9300
S2—C231.822 (4)C6—H60.9300
Cl1—C241.709 (6)C12—C111.359 (5)
Cl2—C241.755 (7)C12—C131.385 (6)
N2—C91.315 (4)C12—H120.9300
N2—C151.405 (4)C18—C191.373 (5)
N1—C41.341 (4)C18—C171.399 (5)
N1—C81.363 (4)C18—C211.478 (5)
N3—C161.346 (4)C17—C161.371 (5)
N3—C201.346 (4)C17—H170.9300
O3—C31.143 (4)C19—H190.9300
O2—C21.159 (4)C16—H160.9300
O1—C11.146 (4)C13—H130.9300
F3—C231.312 (5)C11—H110.9300
C9—C81.445 (4)C21—C221.232 (7)
C8—C71.380 (4)C21—H210.9300
C15—C141.381 (4)C22—H22A0.9300
C15—C101.396 (4)C22—H22B0.9300
F2—C231.311 (5)C24—H24A0.9700
F1—C231.310 (5)C24—H24B0.9700
C2—Re1—C187.73 (14)C6—C5—H5120.1
C2—Re1—C387.46 (14)C4—C5—H5120.1
C1—Re1—C387.51 (14)C15—C14—C13118.5 (3)
C2—Re1—N2101.15 (11)C15—C14—H14120.8
C1—Re1—N295.57 (12)C13—C14—H14120.8
C3—Re1—N2170.94 (11)O1—C1—Re1175.7 (3)
C2—Re1—N1175.15 (11)N3—C20—C19123.1 (3)
C1—Re1—N194.91 (12)N3—C20—H20118.5
C3—Re1—N196.70 (11)C19—C20—H20118.5
N2—Re1—N174.58 (9)C5—C6—C7118.6 (3)
C2—Re1—N390.44 (12)C5—C6—H6120.7
C1—Re1—N3177.94 (11)C7—C6—H6120.7
C3—Re1—N391.46 (12)C11—C12—C13121.6 (3)
N2—Re1—N385.71 (9)C11—C12—H12119.2
N1—Re1—N386.98 (9)C13—C12—H12119.2
C9—S1—C1089.36 (14)C19—C18—C17116.2 (3)
O5—S2—O4114.5 (2)C19—C18—C21120.2 (4)
O5—S2—O6116.1 (2)C17—C18—C21123.5 (4)
O4—S2—O6114.31 (18)C16—C17—C18119.8 (3)
O5—S2—C23103.8 (2)C16—C17—H17120.1
O4—S2—C23103.0 (2)C18—C17—H17120.1
O6—S2—C23102.7 (2)C20—C19—C18121.0 (3)
C9—N2—C15110.7 (2)C20—C19—H19119.5
C9—N2—Re1114.97 (19)C18—C19—H19119.5
C15—N2—Re1134.31 (19)N3—C16—C17123.8 (3)
C4—N1—C8117.8 (2)N3—C16—H16118.1
C4—N1—Re1125.6 (2)C17—C16—H16118.1
C8—N1—Re1116.52 (19)C14—C13—C12121.0 (3)
C16—N3—C20116.0 (3)C14—C13—H13119.5
C16—N3—Re1121.4 (2)C12—C13—H13119.5
C20—N3—Re1121.9 (2)F1—C23—F2107.3 (4)
N2—C9—C8120.2 (3)F1—C23—F3108.6 (4)
N2—C9—S1116.0 (2)F2—C23—F3105.1 (4)
C8—C9—S1123.7 (2)F1—C23—S2110.7 (3)
N1—C8—C7122.1 (3)F2—C23—S2112.7 (3)
N1—C8—C9113.5 (2)F3—C23—S2112.2 (3)
C7—C8—C9124.4 (3)C12—C11—C10117.7 (3)
C14—C15—C10119.6 (3)C12—C11—H11121.2
C14—C15—N2126.9 (3)C10—C11—H11121.2
C10—C15—N2113.5 (3)C22—C21—C18126.4 (5)
O3—C3—Re1179.7 (4)C22—C21—H21116.8
O2—C2—Re1179.2 (3)C18—C21—H21116.8
C11—C10—C15121.6 (3)C21—C22—H22A120.0
C11—C10—S1128.0 (3)C21—C22—H22B120.0
C15—C10—S1110.4 (2)H22A—C22—H22B120.0
C6—C7—C8119.4 (3)Cl1—C24—Cl2113.9 (3)
C6—C7—H7120.3Cl1—C24—H24A108.8
C8—C7—H7120.3Cl2—C24—H24A108.8
N1—C4—C5122.2 (3)Cl1—C24—H24B108.8
N1—C4—H4118.9Cl2—C24—H24B108.8
C5—C4—H4118.9H24A—C24—H24B107.7
C6—C5—C4119.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O6i0.932.653.333 (5)131
C5—H5···O5i0.932.653.278 (5)125
C20—H20···O6i0.932.503.336 (4)150
C11—H11···Cl1ii0.932.983.640 (4)129
C24—H24B···O2iii0.972.283.189 (6)156
Symmetry codes: (i) x, y1, 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) top
Crystal data top
[Re(C7H7N)(C16H10N2S)(CO)3](CF3SO3)·0.28H2OF(000) = 1537
Mr = 791.20Dx = 1.872 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 12.814 (3) ÅCell parameters from 5353 reflections
b = 12.088 (2) Åθ = 2.3–22.0°
c = 18.248 (4) ŵ = 4.55 mm1
β = 96.56 (3)°T = 273 K
V = 2808.0 (10) Å3Block, yellow
Z = 40.15 × 0.12 × 0.10 mm
Data collection top
Bruker APEXII
diffractometer
7054 independent reflections
Radiation source: fine-focus sealed tube5250 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
Detector resolution: 8.33 pixels mm-1θmax = 29.1°, θmin = 2.3°
ω–scansh = 1716
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
k = 1613
Tmin = 0.611, Tmax = 0.746l = 2324
25681 measured reflections
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.050P)2]
where P = (Fo2 + 2Fc2)/3
7054 reflections(Δ/σ)max = 0.001
608 parametersΔρmax = 1.22 e Å3
3097 restraintsΔρmin = 0.71 e Å3
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
Re10.18897 (2)0.26296 (2)0.39241 (2)0.05208 (9)
S10.37198 (12)0.57697 (13)0.46845 (9)0.0829 (4)
O10.0100 (3)0.3433 (4)0.2797 (2)0.0931 (13)
O20.0742 (3)0.0468 (4)0.4173 (2)0.0972 (13)
O30.2720 (3)0.1400 (3)0.2651 (2)0.0839 (12)
N10.1402 (3)0.3616 (3)0.48547 (19)0.0536 (9)
N20.2845 (3)0.4122 (3)0.3965 (2)0.0524 (9)
N30.3207 (3)0.2054 (3)0.4725 (2)0.0536 (9)
C10.0766 (4)0.3141 (5)0.3229 (3)0.0664 (13)
C20.1145 (4)0.1283 (5)0.4077 (3)0.0661 (13)
C30.2425 (4)0.1860 (5)0.3133 (3)0.0633 (13)
C40.0567 (3)0.3445 (4)0.5259 (2)0.0556 (12)
C50.0243 (4)0.2712 (5)0.5001 (3)0.0714 (15)
H50.0225530.2342030.4555810.086*
C60.1065 (5)0.2546 (5)0.5414 (4)0.085 (2)
H60.1607970.2071370.5238090.102*
C70.1100 (5)0.3063 (6)0.6078 (3)0.0845 (18)
H70.1653810.2915190.6352060.101*
C80.0341 (4)0.3786 (6)0.6343 (3)0.0766 (16)
H80.0372830.4134130.6794880.092*
C90.0510 (4)0.4009 (5)0.5922 (3)0.0640 (13)
C100.1287 (5)0.4786 (5)0.6140 (3)0.0836 (17)
H100.1280620.5134840.6594000.100*
C110.1991 (4)0.5031 (5)0.5750 (3)0.0690 (14)
H110.2464140.5595660.5893720.083*
C120.2066 (4)0.4439 (4)0.5082 (3)0.0599 (12)
C130.2836 (3)0.4692 (4)0.4578 (3)0.0556 (11)
C140.4164 (4)0.5428 (5)0.3845 (3)0.0693 (14)
C150.4942 (5)0.5909 (5)0.3493 (4)0.093 (2)
H150.5311740.6518870.3695180.112*
C160.5157 (5)0.5470 (6)0.2841 (4)0.099 (2)
H160.5691430.5778620.2603190.119*
C170.4602 (5)0.4574 (6)0.2518 (3)0.0870 (18)
H170.4764780.4298120.2069460.104*
C180.3813 (4)0.4092 (5)0.2860 (3)0.0670 (13)
H180.3433760.3496760.2643860.080*
C190.3595 (3)0.4513 (4)0.3535 (3)0.0572 (12)
C200.4174 (4)0.2054 (4)0.4533 (3)0.0595 (12)
H200.4289300.2346530.4077610.071*
C210.5021 (4)0.1629 (4)0.4991 (3)0.0608 (12)
H210.5689130.1642950.4839290.073*
C220.4876 (4)0.1188 (4)0.5668 (3)0.0599 (12)
C230.3873 (4)0.1202 (5)0.5863 (3)0.0689 (14)
H230.3739010.0922800.6317440.083*
C240.3060 (4)0.1633 (4)0.5381 (3)0.0630 (13)
H240.2384520.1628220.5521150.076*
C250.5758 (5)0.0727 (5)0.6174 (3)0.0765 (16)
H250.5593340.0347760.6589170.092*
C260.6734 (5)0.0817 (6)0.6079 (4)0.105 (2)
H26A0.6925900.1190850.5669650.126*
H26B0.7246850.0506760.6419110.126*
S20.8300 (7)0.6914 (9)0.1685 (6)0.1007 (17)0.375 (3)
O40.9064 (10)0.6143 (12)0.1993 (7)0.115 (2)0.375 (3)
O50.8707 (11)0.7853 (12)0.1333 (7)0.114 (2)0.375 (3)
O60.7354 (10)0.6459 (11)0.1317 (7)0.118 (2)0.375 (3)
C270.7805 (8)0.7566 (10)0.2528 (9)0.113 (2)0.375 (3)
F10.7387 (9)0.6762 (10)0.2851 (6)0.121 (2)0.375 (3)
F20.7133 (8)0.8304 (9)0.2281 (6)0.121 (2)0.375 (3)
F30.8604 (9)0.7971 (9)0.2914 (6)0.113 (2)0.375 (3)
S2A0.7824 (9)0.6799 (11)0.1667 (6)0.106 (2)0.222 (3)
O4A0.807 (2)0.734 (2)0.1028 (11)0.114 (2)0.222 (3)
O5A0.6703 (14)0.649 (2)0.1560 (14)0.118 (2)0.222 (3)
O6A0.8457 (19)0.5846 (18)0.1929 (13)0.116 (2)0.222 (3)
C27A0.7903 (18)0.7705 (19)0.2512 (12)0.114 (2)0.222 (3)
F1A0.8879 (16)0.7603 (18)0.2795 (13)0.119 (2)0.222 (3)
F2A0.7250 (18)0.7329 (17)0.2936 (12)0.114 (2)0.222 (3)
F3A0.7706 (17)0.8700 (15)0.2263 (11)0.118 (2)0.222 (3)
S2B0.8443 (10)0.6936 (14)0.1676 (10)0.1060 (19)0.279 (2)
O4B0.842 (2)0.771 (2)0.1111 (11)0.114 (2)0.279 (2)
O5B0.9332 (14)0.6202 (19)0.1765 (11)0.112 (2)0.279 (2)
O6B0.831 (2)0.7428 (16)0.2396 (10)0.119 (2)0.279 (2)
C27B0.7202 (17)0.6139 (17)0.1428 (11)0.115 (2)0.279 (2)
F1B0.6484 (11)0.6935 (14)0.1429 (9)0.115 (2)0.279 (2)
F2B0.7244 (12)0.5376 (13)0.1873 (8)0.120 (2)0.279 (2)
F3B0.7442 (12)0.5872 (14)0.0776 (7)0.121 (2)0.279 (2)
O70.8510 (15)0.9029 (18)0.3628 (10)0.129 (3)0.279 (2)
C27C0.7802 (16)0.7569 (15)0.2269 (10)0.117 (2)0.125 (2)
O4C0.797 (3)0.733 (3)0.3024 (12)0.115 (2)0.125 (2)
O5C0.672 (2)0.759 (3)0.193 (2)0.114 (2)0.125 (2)
O6C0.836 (3)0.855 (2)0.2047 (19)0.115 (2)0.125 (2)
S2C0.840 (2)0.644 (2)0.1740 (15)0.115 (2)0.125 (2)
F1C0.940 (2)0.667 (3)0.191 (2)0.113 (2)0.125 (2)
F2C0.807 (3)0.655 (3)0.1059 (13)0.116 (2)0.125 (2)
F3C0.801 (3)0.564 (2)0.2102 (17)0.117 (2)0.125 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Re10.05839 (13)0.05183 (15)0.04699 (13)0.00752 (8)0.01014 (9)0.00218 (8)
S10.0777 (9)0.0666 (10)0.1048 (12)0.0156 (7)0.0120 (8)0.0168 (8)
O10.082 (3)0.117 (4)0.077 (3)0.008 (3)0.004 (2)0.007 (3)
O20.118 (3)0.073 (3)0.106 (3)0.036 (3)0.033 (3)0.010 (2)
O30.099 (3)0.087 (3)0.073 (2)0.020 (2)0.039 (2)0.019 (2)
N10.054 (2)0.058 (3)0.049 (2)0.0052 (18)0.0079 (17)0.0007 (18)
N20.056 (2)0.051 (2)0.051 (2)0.0007 (18)0.0098 (17)0.0068 (18)
N30.069 (3)0.042 (2)0.052 (2)0.0031 (19)0.0122 (19)0.0009 (18)
C10.072 (3)0.068 (4)0.060 (3)0.007 (3)0.014 (3)0.001 (3)
C20.079 (3)0.063 (4)0.057 (3)0.017 (3)0.014 (3)0.008 (3)
C30.077 (3)0.064 (4)0.052 (3)0.016 (3)0.020 (2)0.005 (2)
C40.052 (3)0.065 (3)0.050 (3)0.003 (2)0.009 (2)0.006 (2)
C50.065 (3)0.084 (4)0.067 (3)0.005 (3)0.018 (3)0.010 (3)
C60.074 (4)0.094 (5)0.092 (5)0.014 (3)0.029 (4)0.006 (3)
C70.086 (4)0.097 (5)0.077 (4)0.000 (4)0.040 (3)0.020 (4)
C80.082 (4)0.095 (5)0.057 (3)0.015 (3)0.025 (3)0.004 (3)
C90.069 (3)0.069 (4)0.055 (3)0.006 (3)0.012 (2)0.001 (2)
C100.080 (4)0.086 (5)0.084 (4)0.000 (3)0.003 (3)0.025 (3)
C110.085 (4)0.060 (4)0.062 (3)0.003 (3)0.007 (3)0.023 (3)
C120.062 (3)0.055 (3)0.063 (3)0.003 (2)0.008 (2)0.001 (2)
C130.056 (3)0.047 (3)0.064 (3)0.003 (2)0.006 (2)0.000 (2)
C140.059 (3)0.058 (3)0.092 (4)0.003 (3)0.013 (3)0.011 (3)
C150.076 (4)0.070 (4)0.138 (6)0.014 (3)0.036 (4)0.009 (4)
C160.073 (4)0.096 (5)0.136 (6)0.001 (4)0.045 (4)0.043 (5)
C170.091 (4)0.088 (5)0.087 (4)0.010 (4)0.034 (3)0.028 (4)
C180.077 (3)0.062 (3)0.064 (3)0.001 (3)0.014 (3)0.009 (3)
C190.053 (3)0.048 (3)0.070 (3)0.001 (2)0.009 (2)0.012 (2)
C200.065 (3)0.059 (3)0.056 (3)0.005 (3)0.011 (2)0.004 (2)
C210.059 (3)0.064 (3)0.061 (3)0.009 (2)0.012 (2)0.004 (2)
C220.072 (3)0.045 (3)0.061 (3)0.004 (2)0.002 (3)0.006 (2)
C230.085 (4)0.071 (4)0.051 (3)0.001 (3)0.011 (3)0.010 (3)
C240.069 (3)0.060 (3)0.063 (3)0.003 (3)0.022 (3)0.002 (2)
C250.092 (4)0.067 (4)0.069 (4)0.012 (3)0.005 (3)0.001 (3)
C260.076 (4)0.110 (6)0.126 (6)0.007 (4)0.004 (4)0.035 (5)
S20.114 (4)0.107 (3)0.081 (3)0.043 (3)0.013 (3)0.006 (2)
O40.116 (4)0.128 (4)0.103 (4)0.042 (4)0.017 (4)0.007 (4)
O50.118 (4)0.129 (4)0.099 (4)0.033 (4)0.023 (4)0.014 (4)
O60.116 (4)0.135 (4)0.104 (4)0.031 (4)0.023 (4)0.006 (4)
C270.113 (4)0.128 (4)0.101 (4)0.035 (4)0.024 (4)0.013 (4)
F10.119 (4)0.132 (4)0.114 (4)0.020 (4)0.022 (4)0.024 (4)
F20.116 (4)0.133 (4)0.116 (4)0.045 (4)0.027 (4)0.013 (4)
F30.113 (4)0.120 (4)0.107 (4)0.032 (4)0.017 (4)0.004 (4)
S2A0.113 (4)0.121 (4)0.089 (3)0.032 (4)0.031 (4)0.007 (3)
O4A0.117 (5)0.126 (5)0.102 (4)0.035 (4)0.023 (4)0.014 (4)
O5A0.120 (4)0.130 (4)0.106 (4)0.032 (4)0.020 (4)0.010 (4)
O6A0.118 (4)0.128 (4)0.105 (4)0.033 (4)0.024 (4)0.007 (4)
C27A0.115 (4)0.128 (4)0.102 (4)0.036 (4)0.023 (4)0.010 (4)
F1A0.117 (4)0.130 (5)0.109 (4)0.029 (4)0.016 (4)0.005 (4)
F2A0.117 (4)0.124 (5)0.104 (4)0.033 (4)0.029 (4)0.007 (4)
F3A0.121 (5)0.124 (4)0.110 (4)0.031 (4)0.019 (4)0.010 (4)
S2B0.112 (4)0.112 (4)0.095 (3)0.043 (3)0.016 (3)0.008 (3)
O4B0.117 (5)0.127 (4)0.102 (4)0.033 (4)0.024 (4)0.014 (4)
O5B0.111 (4)0.127 (4)0.100 (4)0.037 (4)0.023 (4)0.012 (4)
O6B0.120 (5)0.132 (4)0.105 (4)0.039 (4)0.018 (4)0.009 (4)
C27B0.116 (4)0.130 (4)0.102 (4)0.034 (4)0.023 (4)0.011 (4)
F1B0.114 (4)0.128 (4)0.106 (4)0.040 (4)0.017 (4)0.014 (4)
F2B0.117 (4)0.129 (4)0.115 (4)0.033 (4)0.022 (4)0.017 (4)
F3B0.124 (5)0.134 (5)0.107 (4)0.036 (4)0.018 (4)0.002 (4)
O70.128 (6)0.145 (6)0.117 (6)0.026 (6)0.026 (6)0.008 (6)
C27C0.115 (4)0.130 (4)0.107 (4)0.039 (4)0.024 (4)0.011 (4)
O4C0.117 (5)0.127 (5)0.104 (4)0.036 (4)0.020 (4)0.010 (4)
O5C0.114 (4)0.127 (5)0.104 (4)0.035 (4)0.021 (4)0.007 (4)
O6C0.116 (5)0.128 (4)0.105 (4)0.034 (4)0.023 (4)0.009 (4)
S2C0.116 (4)0.127 (4)0.103 (4)0.035 (4)0.022 (4)0.010 (4)
F1C0.114 (4)0.127 (5)0.102 (4)0.036 (4)0.023 (4)0.011 (4)
F2C0.117 (5)0.128 (5)0.105 (4)0.034 (4)0.022 (4)0.009 (4)
F3C0.118 (5)0.127 (4)0.106 (4)0.033 (4)0.020 (4)0.010 (4)
Geometric parameters (Å, º) top
Re1—C31.909 (5)C18—H180.9300
Re1—C11.910 (6)C20—C211.390 (7)
Re1—C21.924 (6)C20—H200.9300
Re1—N22.176 (4)C21—C221.377 (7)
Re1—N32.214 (4)C21—H210.9300
Re1—N12.222 (4)C22—C231.373 (7)
S1—C131.723 (5)C22—C251.484 (7)
S1—C141.744 (6)C23—C241.385 (7)
O1—C11.149 (6)C23—H230.9300
O2—C21.135 (6)C24—H240.9300
O3—C31.142 (5)C25—C261.287 (8)
N1—C121.343 (6)C25—H250.9300
N1—C41.384 (5)C26—H26A0.9300
N2—C131.315 (6)C26—H26B0.9300
N2—C191.391 (5)S2—O41.420 (8)
N3—C201.326 (6)S2—O61.427 (9)
N3—C241.335 (6)S2—O51.432 (8)
C4—C91.397 (6)S2—C271.90 (2)
C4—C51.405 (7)C27—F31.272 (9)
C5—C61.378 (8)C27—F11.284 (9)
C5—H50.9300C27—F21.286 (9)
C6—C71.369 (9)S2A—O4A1.402 (15)
C6—H60.9300S2A—O6A1.458 (16)
C7—C81.356 (8)S2A—O5A1.475 (16)
C7—H70.9300S2A—C27A1.88 (2)
C8—C91.430 (7)C27A—F2A1.285 (18)
C8—H80.9300C27A—F3A1.300 (18)
C9—C101.394 (8)C27A—F1A1.303 (19)
C10—C111.247 (7)S2B—O4B1.394 (14)
C10—H100.9300S2B—O5B1.438 (14)
C11—C121.427 (6)S2B—O6B1.471 (18)
C11—H110.9300S2B—C27B1.87 (2)
C12—C131.455 (6)C27B—F2B1.225 (17)
C14—C151.375 (7)C27B—F3B1.304 (18)
C14—C191.408 (7)C27B—F1B1.331 (17)
C15—C161.359 (9)C27C—O4C1.399 (17)
C15—H150.9300C27C—O5C1.457 (17)
C16—C171.388 (9)C27C—O6C1.466 (18)
C16—H160.9300C27C—S2C1.88 (2)
C17—C181.377 (7)S2C—F2C1.271 (19)
C17—H170.9300S2C—F3C1.307 (19)
C18—C191.390 (7)S2C—F1C1.321 (19)
C3—Re1—C187.9 (2)C18—C19—N2126.7 (5)
C3—Re1—C285.7 (2)C18—C19—C14119.7 (5)
C1—Re1—C291.2 (2)N2—C19—C14113.6 (5)
C3—Re1—N2100.42 (18)N3—C20—C21122.0 (5)
C1—Re1—N297.63 (19)N3—C20—H20119.0
C2—Re1—N2169.40 (18)C21—C20—H20119.0
C3—Re1—N391.92 (19)C22—C21—C20120.5 (5)
C1—Re1—N3179.21 (19)C22—C21—H21119.8
C2—Re1—N389.5 (2)C20—C21—H21119.8
N2—Re1—N381.63 (14)C23—C22—C21117.0 (5)
C3—Re1—N1174.73 (18)C23—C22—C25120.8 (5)
C1—Re1—N194.45 (18)C21—C22—C25122.2 (5)
C2—Re1—N198.97 (18)C22—C23—C24119.9 (5)
N2—Re1—N174.63 (14)C22—C23—H23120.0
N3—Re1—N185.63 (13)C24—C23—H23120.0
C13—S1—C1489.9 (2)N3—C24—C23122.7 (5)
C12—N1—C4116.6 (4)N3—C24—H24118.7
C12—N1—Re1114.2 (3)C23—C24—H24118.7
C4—N1—Re1129.0 (3)C26—C25—C22124.5 (6)
C13—N2—C19112.1 (4)C26—C25—H25117.7
C13—N2—Re1113.8 (3)C22—C25—H25117.7
C19—N2—Re1133.2 (3)C25—C26—H26A120.0
C20—N3—C24118.0 (4)C25—C26—H26B120.0
C20—N3—Re1119.4 (3)H26A—C26—H26B120.0
C24—N3—Re1122.5 (3)O4—S2—O6116.4 (7)
O1—C1—Re1178.2 (5)O4—S2—O5115.3 (6)
O2—C2—Re1177.3 (5)O6—S2—O5115.3 (7)
O3—C3—Re1178.3 (5)O4—S2—C27103.3 (7)
N1—C4—C9120.6 (4)O6—S2—C27101.3 (7)
N1—C4—C5120.2 (4)O5—S2—C27101.9 (7)
C9—C4—C5119.2 (4)F3—C27—F1113.0 (10)
C6—C5—C4119.4 (6)F3—C27—F2113.0 (10)
C6—C5—H5120.3F1—C27—F2112.9 (10)
C4—C5—H5120.3F3—C27—S2106.6 (10)
C7—C6—C5121.5 (6)F1—C27—S2104.6 (10)
C7—C6—H6119.2F2—C27—S2106.0 (10)
C5—C6—H6119.2O4A—S2A—O6A118.1 (16)
C8—C7—C6121.0 (5)O4A—S2A—O5A108.2 (15)
C8—C7—H7119.5O6A—S2A—O5A110.0 (15)
C6—C7—H7119.5O4A—S2A—C27A114.5 (15)
C7—C8—C9119.3 (5)O6A—S2A—C27A102.4 (12)
C7—C8—H8120.3O5A—S2A—C27A102.5 (12)
C9—C8—H8120.3F2A—C27A—F3A115 (2)
C10—C9—C4118.0 (5)F2A—C27A—F1A113 (2)
C10—C9—C8122.5 (5)F3A—C27A—F1A111 (2)
C4—C9—C8119.5 (5)F2A—C27A—S2A108.0 (17)
C11—C10—C9122.5 (6)F3A—C27A—S2A105.1 (15)
C11—C10—H10118.8F1A—C27A—S2A103.2 (16)
C9—C10—H10118.8O4B—S2B—O5B116.5 (15)
C10—C11—C12119.5 (5)O4B—S2B—O6B113.2 (17)
C10—C11—H11120.3O5B—S2B—O6B108.7 (14)
C12—C11—H11120.3O4B—S2B—C27B103.1 (13)
N1—C12—C11122.3 (4)O5B—S2B—C27B110.5 (13)
N1—C12—C13114.3 (4)O6B—S2B—C27B104.0 (12)
C11—C12—C13123.4 (5)F2B—C27B—F3B114.9 (18)
N2—C13—C12120.0 (4)F2B—C27B—F1B121.4 (18)
N2—C13—S1115.0 (3)F3B—C27B—F1B114.5 (17)
C12—C13—S1124.9 (4)F2B—C27B—S2B104.8 (16)
C15—C14—C19121.0 (6)F3B—C27B—S2B93.8 (14)
C15—C14—S1129.6 (5)F1B—C27B—S2B101.3 (15)
C19—C14—S1109.4 (4)O4C—C27C—O5C117 (2)
C16—C15—C14118.3 (6)O4C—C27C—O6C114 (2)
C16—C15—H15120.9O5C—C27C—O6C110.1 (18)
C14—C15—H15120.9O4C—C27C—S2C109.5 (17)
C15—C16—C17122.0 (6)O5C—C27C—S2C102.4 (16)
C15—C16—H16119.0O6C—C27C—S2C101.7 (15)
C17—C16—H16119.0F2C—S2C—F3C118 (2)
C18—C17—C16120.4 (6)F2C—S2C—F1C114 (2)
C18—C17—H17119.8F3C—S2C—F1C117 (2)
C16—C17—H17119.8F2C—S2C—C27C109 (2)
C17—C18—C19118.6 (6)F3C—S2C—C27C94.5 (18)
C17—C18—H18120.7F1C—S2C—C27C99.8 (19)
C19—C18—H18120.7
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···F1Bi0.932.333.045 (17)134
C11—H11···O5ii0.932.533.459 (16)178
C11—H11···O4Aii0.932.623.48 (3)154
C11—H11···F3Aii0.932.623.199 (19)121
C11—H11···O4Bii0.932.393.31 (3)168
C11—H11···O6Cii0.932.503.27 (3)140
C21—H21···O4Aiii0.932.523.35 (3)150
C21—H21···O4Biii0.932.533.26 (3)136
C21—H21···F2Ciii0.932.413.27 (3)154
C23—H23···O6Aiv0.932.463.23 (2)141
C23—H23···F3Civ0.932.613.44 (3)150
C24—H24···O7v0.932.182.96 (2)141
Symmetry codes: (i) x+1/2, y1/2, z+1/2; (ii) x1/2, y+3/2, z+1/2; (iii) x+3/2, y1/2, z+1/2; (iv) x1/2, 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) top
Crystal data top
[Re(C7H7N)(C12H8N2)(CO)3](CF3SO3)F(000) = 1360
Mr = 704.64Dx = 1.905 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 12.398 (2) ÅCell parameters from 9930 reflections
b = 12.878 (3) Åθ = 2.6–29.0°
c = 15.393 (3) ŵ = 5.10 mm1
β = 91.83 (3)°T = 296 K
V = 2456.5 (8) Å3Block, yellow
Z = 40.18 × 0.15 × 0.12 mm
Data collection top
Bruker APEXII CCD
diffractometer
5011 independent reflections
Radiation source: fine-focus sealed tube4517 reflections with I > 2σ(I)
Detector resolution: 8.33 pixels mm-1Rint = 0.019
ω scansθmax = 26.4°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Krause et al., 2015)
h = 1515
Tmin = 0.490, Tmax = 0.746k = 1616
23150 measured reflectionsl = 1919
Refinement top
Refinement on F2Primary atom site location: dual
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.019Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.046H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0207P)2 + 1.7702P]
where P = (Fo2 + 2Fc2)/3
5011 reflections(Δ/σ)max = 0.002
481 parametersΔρmax = 1.23 e Å3
913 restraintsΔρmin = 0.58 e Å3
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
Re10.42304 (2)0.73137 (2)0.21775 (2)0.04579 (5)
N20.52880 (17)0.60262 (17)0.18745 (14)0.0461 (5)
N10.32397 (17)0.63066 (19)0.13343 (13)0.0490 (5)
O20.2581 (2)0.9037 (2)0.24925 (16)0.0818 (7)
N30.35773 (17)0.63088 (17)0.32066 (13)0.0466 (5)
C150.3724 (2)0.5393 (2)0.11144 (15)0.0464 (6)
O10.5148 (2)0.8662 (2)0.07393 (17)0.0877 (8)
O30.5783 (2)0.8415 (2)0.34638 (19)0.0982 (9)
C140.4820 (2)0.5247 (2)0.13976 (16)0.0448 (6)
C70.3203 (2)0.4620 (3)0.06156 (18)0.0567 (7)
C20.3188 (3)0.8387 (2)0.23759 (18)0.0580 (7)
C200.2551 (2)0.6396 (2)0.3453 (2)0.0607 (7)
H200.2108740.6882400.3171220.073*
C190.2123 (3)0.5804 (3)0.4098 (2)0.0664 (8)
H190.1410840.5905690.4250050.080*
C130.6335 (2)0.5932 (2)0.20978 (19)0.0563 (7)
H130.6668110.6465330.2413020.068*
C180.2744 (3)0.5058 (2)0.45257 (18)0.0571 (7)
C100.5384 (2)0.4349 (2)0.11669 (18)0.0552 (7)
C10.4799 (3)0.8149 (3)0.1269 (2)0.0604 (7)
C120.6942 (2)0.5077 (3)0.1880 (2)0.0641 (8)
H120.7670460.5045960.2043200.077*
C90.4823 (3)0.3574 (3)0.0673 (2)0.0684 (8)
H90.5181010.2966420.0529680.082*
C30.5199 (3)0.8009 (3)0.2981 (2)0.0632 (8)
C80.3792 (3)0.3698 (3)0.0411 (2)0.0677 (9)
H80.3449870.3175000.0089620.081*
C110.6476 (3)0.4288 (3)0.1431 (2)0.0635 (8)
H110.6878500.3703230.1295740.076*
C170.3790 (2)0.4955 (3)0.42603 (19)0.0631 (8)
H170.4239500.4455220.4516110.076*
C160.4171 (2)0.5585 (3)0.36214 (18)0.0581 (7)
H160.4885370.5503750.3466900.070*
C40.2222 (2)0.6453 (3)0.10613 (19)0.0653 (8)
H40.1878740.7067570.1209040.078*
C50.1650 (3)0.5721 (4)0.0561 (2)0.0781 (10)
H50.0940630.5852080.0378450.094*
C60.2133 (3)0.4815 (3)0.0343 (2)0.0727 (9)
H60.1754020.4324230.0012280.087*
C210.2291 (3)0.4412 (3)0.5215 (2)0.0742 (9)
H210.1629160.4612530.5428850.089*
C220.2735 (4)0.3597 (4)0.5546 (3)0.0947 (13)
H22A0.3397050.3371110.5349960.114*
H22B0.2394840.3232260.5980420.114*
S10.9375 (10)0.7116 (11)0.1976 (8)0.065 (2)0.338 (3)
O41.0403 (16)0.763 (2)0.2104 (18)0.088 (6)0.338 (3)
O50.935 (3)0.6151 (16)0.1495 (17)0.099 (7)0.338 (3)
O60.867 (2)0.717 (2)0.2706 (15)0.067 (5)0.338 (3)
C230.8688 (15)0.7977 (18)0.1175 (13)0.077 (4)0.338 (3)
F10.874 (2)0.8943 (16)0.142 (2)0.112 (7)0.338 (3)
F20.7677 (13)0.774 (2)0.1097 (16)0.128 (7)0.338 (3)
F30.9157 (14)0.7899 (19)0.0422 (11)0.113 (5)0.338 (3)
S1A0.8979 (4)0.7746 (4)0.1201 (5)0.0665 (14)0.345 (3)
O4A0.904 (3)0.8784 (13)0.1573 (18)0.107 (8)0.345 (3)
O5A0.7913 (13)0.7302 (15)0.1055 (15)0.103 (5)0.345 (3)
O6A0.9783 (19)0.7510 (19)0.0562 (14)0.104 (6)0.345 (3)
C23A0.9499 (16)0.6969 (16)0.2134 (14)0.078 (4)0.345 (3)
F1A0.8853 (19)0.697 (2)0.2776 (14)0.093 (6)0.345 (3)
F2A1.0429 (17)0.730 (2)0.2428 (18)0.122 (7)0.345 (3)
F3A0.9658 (14)0.6012 (11)0.1916 (8)0.117 (4)0.345 (3)
S1B0.9353 (9)0.6983 (12)0.2016 (8)0.060 (2)0.317 (3)
O4B1.0393 (16)0.740 (2)0.2292 (19)0.074 (6)0.317 (3)
O5B0.938 (2)0.6004 (15)0.1562 (19)0.080 (6)0.317 (3)
O6B0.847 (2)0.715 (3)0.2596 (17)0.084 (7)0.317 (3)
C23B0.8960 (16)0.7879 (17)0.1123 (14)0.065 (4)0.317 (3)
F1B0.896 (2)0.8851 (14)0.1382 (16)0.074 (4)0.317 (3)
F2B0.7981 (14)0.767 (2)0.0835 (14)0.119 (6)0.317 (3)
F3B0.9622 (19)0.7795 (18)0.0484 (14)0.098 (6)0.317 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Re10.05067 (7)0.04491 (7)0.04193 (7)0.00107 (4)0.00364 (4)0.00007 (4)
N20.0446 (12)0.0493 (13)0.0448 (11)0.0015 (9)0.0067 (9)0.0027 (9)
N10.0453 (12)0.0623 (14)0.0395 (11)0.0006 (10)0.0040 (9)0.0011 (10)
O20.1036 (19)0.0689 (15)0.0740 (15)0.0352 (14)0.0189 (13)0.0060 (12)
N30.0498 (12)0.0497 (13)0.0404 (11)0.0018 (10)0.0036 (9)0.0000 (9)
C150.0529 (15)0.0526 (15)0.0344 (12)0.0067 (12)0.0105 (10)0.0016 (11)
O10.0976 (19)0.0872 (18)0.0798 (16)0.0107 (15)0.0258 (14)0.0259 (14)
O30.107 (2)0.0866 (19)0.099 (2)0.0201 (16)0.0338 (16)0.0172 (16)
C140.0491 (14)0.0470 (14)0.0388 (12)0.0042 (11)0.0096 (10)0.0044 (10)
C70.0617 (18)0.0679 (19)0.0408 (14)0.0148 (14)0.0056 (12)0.0006 (13)
C20.075 (2)0.0554 (17)0.0433 (14)0.0049 (15)0.0064 (13)0.0038 (12)
C200.0604 (18)0.0581 (18)0.0644 (18)0.0136 (14)0.0142 (14)0.0066 (14)
C190.0613 (19)0.069 (2)0.070 (2)0.0053 (15)0.0228 (15)0.0020 (16)
C130.0458 (15)0.0622 (18)0.0611 (17)0.0028 (13)0.0042 (12)0.0057 (14)
C180.0666 (18)0.0613 (18)0.0439 (14)0.0074 (14)0.0081 (13)0.0002 (13)
C100.0700 (19)0.0473 (15)0.0491 (15)0.0006 (13)0.0140 (13)0.0065 (12)
C10.0653 (18)0.0574 (18)0.0588 (17)0.0012 (15)0.0059 (14)0.0007 (15)
C120.0499 (16)0.070 (2)0.073 (2)0.0056 (15)0.0094 (14)0.0128 (16)
C90.091 (2)0.0506 (18)0.0641 (19)0.0028 (16)0.0107 (17)0.0035 (14)
C30.074 (2)0.0524 (17)0.0633 (19)0.0022 (15)0.0017 (16)0.0006 (15)
C80.095 (3)0.0555 (18)0.0529 (17)0.0155 (17)0.0081 (16)0.0084 (14)
C110.0640 (19)0.0597 (19)0.0679 (19)0.0152 (15)0.0186 (15)0.0139 (15)
C170.0597 (18)0.076 (2)0.0535 (16)0.0012 (15)0.0025 (13)0.0189 (15)
C160.0464 (15)0.075 (2)0.0531 (16)0.0034 (14)0.0027 (12)0.0113 (14)
C40.0529 (17)0.090 (2)0.0533 (17)0.0101 (16)0.0006 (13)0.0065 (16)
C50.0502 (18)0.123 (3)0.0608 (19)0.0040 (19)0.0067 (14)0.012 (2)
C60.072 (2)0.093 (3)0.0528 (17)0.0194 (19)0.0009 (15)0.0135 (17)
C210.086 (2)0.076 (2)0.0607 (19)0.0141 (19)0.0153 (17)0.0077 (17)
C220.115 (3)0.098 (3)0.073 (2)0.022 (3)0.011 (2)0.025 (2)
S10.068 (4)0.061 (4)0.069 (4)0.007 (2)0.022 (3)0.009 (3)
O40.065 (6)0.094 (10)0.105 (15)0.017 (5)0.007 (6)0.013 (9)
O50.131 (14)0.069 (8)0.098 (12)0.007 (8)0.018 (10)0.026 (8)
O60.066 (11)0.080 (9)0.055 (7)0.002 (10)0.011 (7)0.009 (6)
C230.092 (8)0.078 (7)0.060 (7)0.017 (7)0.000 (6)0.002 (6)
F10.139 (14)0.073 (6)0.123 (12)0.013 (6)0.017 (9)0.007 (7)
F20.085 (7)0.142 (13)0.154 (14)0.017 (7)0.015 (7)0.021 (11)
F30.155 (13)0.129 (10)0.057 (5)0.003 (10)0.020 (7)0.005 (5)
S1A0.068 (2)0.060 (2)0.071 (3)0.0102 (18)0.007 (2)0.015 (2)
O4A0.160 (18)0.074 (7)0.091 (14)0.014 (8)0.033 (11)0.027 (8)
O5A0.094 (8)0.123 (13)0.089 (9)0.047 (8)0.021 (7)0.002 (8)
O6A0.143 (11)0.095 (13)0.077 (8)0.038 (8)0.039 (7)0.005 (7)
C23A0.064 (8)0.093 (8)0.077 (8)0.006 (8)0.014 (6)0.009 (7)
F1A0.091 (9)0.113 (12)0.077 (7)0.008 (7)0.021 (7)0.002 (6)
F2A0.077 (7)0.187 (15)0.102 (12)0.012 (8)0.012 (6)0.008 (10)
F3A0.162 (11)0.087 (6)0.103 (9)0.036 (6)0.032 (7)0.008 (5)
S1B0.049 (3)0.064 (4)0.066 (4)0.010 (2)0.003 (3)0.004 (3)
O4B0.039 (6)0.113 (16)0.069 (11)0.009 (7)0.007 (6)0.018 (10)
O5B0.086 (11)0.056 (6)0.102 (14)0.004 (6)0.037 (10)0.002 (6)
O6B0.073 (10)0.102 (13)0.079 (10)0.030 (8)0.025 (9)0.021 (9)
C23B0.075 (9)0.062 (7)0.055 (8)0.003 (7)0.018 (6)0.005 (6)
F1B0.091 (9)0.058 (6)0.072 (9)0.009 (6)0.002 (6)0.004 (5)
F2B0.098 (9)0.138 (13)0.117 (12)0.021 (9)0.058 (9)0.002 (10)
F3B0.140 (14)0.080 (11)0.075 (8)0.005 (11)0.027 (10)0.011 (7)
Geometric parameters (Å, º) top
Re1—C11.917 (3)C11—H110.9300
Re1—C31.918 (3)C17—C161.371 (4)
Re1—C21.923 (3)C17—H170.9300
Re1—N22.174 (2)C16—H160.9300
Re1—N12.185 (2)C4—C51.397 (5)
Re1—N32.218 (2)C4—H40.9300
N2—C131.338 (3)C5—C61.358 (5)
N2—C141.363 (3)C5—H50.9300
N1—C41.330 (4)C6—H60.9300
N1—C151.369 (4)C21—C221.283 (6)
O2—C21.144 (4)C21—H210.9300
N3—C161.338 (4)C22—H22A0.9300
N3—C201.344 (4)C22—H22B0.9300
C15—C71.402 (4)S1—O41.445 (12)
C15—C141.426 (4)S1—O61.445 (12)
O1—C11.145 (4)S1—O51.446 (11)
O3—C31.147 (4)S1—C231.845 (17)
C14—C101.402 (4)C23—F21.293 (14)
C7—C61.400 (5)C23—F11.302 (14)
C7—C81.434 (5)C23—F31.317 (13)
C20—C191.373 (4)S1A—O5A1.450 (12)
C20—H200.9300S1A—O4A1.456 (14)
C19—C181.384 (4)S1A—O6A1.456 (12)
C19—H190.9300S1A—C23A1.849 (18)
C13—C121.381 (4)C23A—F1A1.291 (15)
C13—H130.9300C23A—F3A1.293 (16)
C18—C171.379 (4)C23A—F2A1.298 (15)
C18—C211.473 (4)S1B—O5B1.443 (12)
C10—C111.403 (4)S1B—O6B1.446 (13)
C10—C91.423 (4)S1B—O4B1.450 (12)
C12—C111.350 (5)S1B—C23B1.85 (2)
C12—H120.9300C23B—F2B1.306 (14)
C9—C81.337 (5)C23B—F3B1.306 (15)
C9—H90.9300C23B—F1B1.313 (14)
C8—H80.9300
C1—Re1—C388.35 (14)C12—C11—C10119.9 (3)
C1—Re1—C288.70 (13)C12—C11—H11120.0
C3—Re1—C288.39 (14)C10—C11—H11120.0
C1—Re1—N291.89 (11)C16—C17—C18120.3 (3)
C3—Re1—N297.18 (12)C16—C17—H17119.8
C2—Re1—N2174.41 (11)C18—C17—H17119.8
C1—Re1—N196.48 (11)N3—C16—C17123.9 (3)
C3—Re1—N1171.39 (11)N3—C16—H16118.0
C2—Re1—N198.81 (11)C17—C16—H16118.0
N2—Re1—N175.59 (8)N1—C4—C5122.5 (3)
C1—Re1—N3178.44 (11)N1—C4—H4118.7
C3—Re1—N392.69 (12)C5—C4—H4118.7
C2—Re1—N392.49 (11)C6—C5—C4119.7 (3)
N2—Re1—N386.83 (8)C6—C5—H5120.1
N1—Re1—N382.34 (8)C4—C5—H5120.1
C13—N2—C14117.7 (2)C5—C6—C7120.1 (3)
C13—N2—Re1126.9 (2)C5—C6—H6120.0
C14—N2—Re1115.35 (17)C7—C6—H6120.0
C4—N1—C15117.6 (3)C22—C21—C18125.3 (4)
C4—N1—Re1127.8 (2)C22—C21—H21117.3
C15—N1—Re1114.49 (17)C18—C21—H21117.3
C16—N3—C20115.8 (2)C21—C22—H22A120.0
C16—N3—Re1122.66 (18)C21—C22—H22B120.0
C20—N3—Re1121.51 (19)H22A—C22—H22B120.0
N1—C15—C7123.2 (3)O4—S1—O6115.0 (14)
N1—C15—C14117.3 (2)O4—S1—O5118.1 (14)
C7—C15—C14119.5 (3)O6—S1—O5115.8 (14)
N2—C14—C10122.4 (2)O4—S1—C23101.6 (11)
N2—C14—C15116.9 (2)O6—S1—C23102.3 (11)
C10—C14—C15120.6 (3)O5—S1—C2399.9 (11)
C6—C7—C15116.9 (3)F2—C23—F1107.3 (17)
C6—C7—C8124.5 (3)F2—C23—F3110.7 (16)
C15—C7—C8118.6 (3)F1—C23—F3108.0 (17)
O2—C2—Re1178.9 (3)F2—C23—S1110.2 (15)
N3—C20—C19123.3 (3)F1—C23—S1111.1 (16)
N3—C20—H20118.4F3—C23—S1109.5 (13)
C19—C20—H20118.4O5A—S1A—O4A117.4 (14)
C20—C19—C18120.5 (3)O5A—S1A—O6A116.9 (13)
C20—C19—H19119.7O4A—S1A—O6A115.3 (14)
C18—C19—H19119.7O5A—S1A—C23A101.6 (9)
N2—C13—C12122.8 (3)O4A—S1A—C23A100.3 (11)
N2—C13—H13118.6O6A—S1A—C23A100.5 (10)
C12—C13—H13118.6F1A—C23A—F3A107.7 (18)
C17—C18—C19116.1 (3)F1A—C23A—F2A107.3 (19)
C17—C18—C21122.9 (3)F3A—C23A—F2A105.1 (18)
C19—C18—C21121.0 (3)F1A—C23A—S1A112.6 (16)
C14—C10—C11117.2 (3)F3A—C23A—S1A111.5 (13)
C14—C10—C9118.3 (3)F2A—C23A—S1A112.2 (16)
C11—C10—C9124.5 (3)O5B—S1B—O6B117.1 (15)
O1—C1—Re1178.6 (3)O5B—S1B—O4B115.8 (14)
C11—C12—C13119.8 (3)O6B—S1B—O4B116.4 (15)
C11—C12—H12120.1O5B—S1B—C23B101.3 (12)
C13—C12—H12120.1O6B—S1B—C23B100.5 (13)
C8—C9—C10121.6 (3)O4B—S1B—C23B101.3 (12)
C8—C9—H9119.2F2B—C23B—F3B109.0 (18)
C10—C9—H9119.2F2B—C23B—F1B106.9 (18)
O3—C3—Re1179.3 (3)F3B—C23B—F1B108.1 (17)
C9—C8—C7121.4 (3)F2B—C23B—S1B110.3 (15)
C9—C8—H8119.3F3B—C23B—S1B110.6 (15)
C7—C8—H8119.3F1B—C23B—S1B111.8 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C20—H20···F2Ai0.932.403.24 (2)149
C20—H20···O4Bi0.932.573.42 (2)152
C13—H13···O6B0.932.413.15 (3)136
C12—H12···O5B0.932.583.30 (2)135
C17—H17···F3Bii0.932.563.42 (3)154
C16—H16···N20.932.613.116 (4)115
C16—H16···F1ii0.932.633.34 (3)133
C16—H16···O4Aii0.932.583.23 (3)127
C16—H16···F1Bii0.932.573.22 (2)127
C4—H4···O4i0.932.443.19 (3)139
C4—H4···O4Bi0.932.563.24 (3)130
C5—H5···O6Ai0.932.593.27 (2)130
Symmetry codes: (i) x1, y, z; (ii) x+3/2, y1/2, z+1/2.
 

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