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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
CCDC references: 1564139; 1564138; 1564137
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)·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 Å3 | 0.20 × 0.18 × 0.15 mm |
Data collection top
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 top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.020 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.051 | H-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 parameters | Δρmax = 0.91 e Å−3 |
0 restraints | Δρmin = −0.73 e Å−3 |
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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4···O6i | 0.93 | 2.65 | 3.333 (5) | 131 |
C5—H5···O5i | 0.93 | 2.65 | 3.278 (5) | 125 |
C20—H20···O6i | 0.93 | 2.50 | 3.336 (4) | 150 |
C11—H11···Cl1ii | 0.93 | 2.98 | 3.640 (4) | 129 |
C24—H24B···O2iii | 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)
top
Crystal data top
[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) Å3 | Block, yellow |
Z = 4 | 0.15 × 0.12 × 0.10 mm |
Data collection top
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 top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.104 | H-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 parameters | Δρmax = 1.22 e Å−3 |
3097 restraints | Δρmin = −0.71 e Å−3 |
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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···F1Bi | 0.93 | 2.33 | 3.045 (17) | 134 |
C11—H11···O5ii | 0.93 | 2.53 | 3.459 (16) | 178 |
C11—H11···O4Aii | 0.93 | 2.62 | 3.48 (3) | 154 |
C11—H11···F3Aii | 0.93 | 2.62 | 3.199 (19) | 121 |
C11—H11···O4Bii | 0.93 | 2.39 | 3.31 (3) | 168 |
C11—H11···O6Cii | 0.93 | 2.50 | 3.27 (3) | 140 |
C21—H21···O4Aiii | 0.93 | 2.52 | 3.35 (3) | 150 |
C21—H21···O4Biii | 0.93 | 2.53 | 3.26 (3) | 136 |
C21—H21···F2Ciii | 0.93 | 2.41 | 3.27 (3) | 154 |
C23—H23···O6Aiv | 0.93 | 2.46 | 3.23 (2) | 141 |
C23—H23···F3Civ | 0.93 | 2.61 | 3.44 (3) | 150 |
C24—H24···O7v | 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)
top
Crystal data top
[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) Å3 | Block, yellow |
Z = 4 | 0.18 × 0.15 × 0.12 mm |
Data collection top
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 top
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.019 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.046 | H-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 parameters | Δρmax = 1.23 e Å−3 |
913 restraints | Δρmin = −0.58 e Å−3 |
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 | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
C20—H20···F2Ai | 0.93 | 2.40 | 3.24 (2) | 149 |
C20—H20···O4Bi | 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···F3Bii | 0.93 | 2.56 | 3.42 (3) | 154 |
C16—H16···N2 | 0.93 | 2.61 | 3.116 (4) | 115 |
C16—H16···F1ii | 0.93 | 2.63 | 3.34 (3) | 133 |
C16—H16···O4Aii | 0.93 | 2.58 | 3.23 (3) | 127 |
C16—H16···F1Bii | 0.93 | 2.57 | 3.22 (2) | 127 |
C4—H4···O4i | 0.93 | 2.44 | 3.19 (3) | 139 |
C4—H4···O4Bi | 0.93 | 2.56 | 3.24 (3) | 130 |
C5—H5···O6Ai | 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. |
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