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The synthesis and crystal structures of two new rhenium(I) complexes obtained utilizing benzhydroxamic acid (BHAH) and 3-hydroxyflavone (2-phenylchromen-4-one, FlavH) as bidentate ligands, namely tetraethylammonium
fac-(benzhydroxamato-κ
2O,
O′)bromidotricarbonylrhenate(I), (C
8H
20N)[ReBr(C
7H
6NO
2)(CO)
3],
1, and
fac-aquatricarbonyl(4-oxo-2-phenylchromen-3-olato-κ
2O,
O′)rhenium(I)–3-hydroxyflavone (1/1), [Re(C
15H
9O
3)(CO)
3(H
2O)]·C
15H
10O
3,
3, are reported. Furthermore, the crystal structure of free 3-hydroxyflavone, C
15H
10O
3,
4, was redetermined at 100 K in order to compare the packing trends and solid-state NMR spectroscopy with that of the solvate flavone molecule in
3. The compounds were characterized in solution by
1H and
13C NMR spectroscopy, and in the solid state by
13C NMR spectroscopy using the cross-polarization magic angle spinning (CP/MAS) technique. Compounds
1 and
3 both crystallize in the triclinic space group
P with one molecule in the asymmetric unit, while
4 crystallizes in the orthorhombic space group
P2
12
12
1. Molecules of
1 and
3 generate one-dimensional chains formed through intermolecular interactions. A comparison of the coordinated 3-hydroxyflavone ligand with the uncoordinated solvate molecule and free molecule
4 shows that the last two are virtually completely planar due to hydrogen-bonding interactions, as opposed to the former, which is able to rotate more freely. The differences between the solid- and solution-state
13C NMR spectra of
3 and
4 are ascribed to inter- and intramolecular interactions. The study also investigated the potential labelling of both bidentate ligands with the corresponding
fac-
99mTc-tricarbonyl synthon. All attempts were unsuccessful and reasons for this are provided.
Supporting information
CCDC references: 1580730; 1580732; 1580731
For all structures, data collection: APEX2 (Bruker, 2008); cell refinement: SAINT-Plus (Bruker, 2008); data reduction: SAINT-Plus (Bruker, 2008) and XPREP (Bruker, 2008); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: WinGX (Farrugia, 2012) and SHELXL2018 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: SHELXL2018 (Sheldrick, 2015).
Tetraethylammonium
fac-(benzhydroxamato-
κ2O,
O')bromidotricarbonylrhenate(I) (7LMaSc1)
top
Crystal data top
(C8H20N)[ReBr(C7H6NO2)(CO)3] | Z = 2 |
Mr = 616.52 | F(000) = 596 |
Triclinic, P1 | Dx = 1.987 Mg m−3 |
a = 9.6321 (13) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.8793 (11) Å | Cell parameters from 5976 reflections |
c = 12.826 (2) Å | θ = 2.5–28.3° |
α = 95.806 (10)° | µ = 7.87 mm−1 |
β = 108.520 (11)° | T = 100 K |
γ = 112.895 (7)° | Cuboid, colourless |
V = 1030.2 (3) Å3 | 0.38 × 0.25 × 0.11 mm |
Data collection top
CCD area detector diffractometer | 4720 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.038 |
phi and ω scans | θmax = 28.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −12→12 |
Tmin = 0.109, Tmax = 0.421 | k = −13→13 |
18080 measured reflections | l = −16→16 |
4957 independent reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.021 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.049 | w = 1/[σ2(Fo2) + (0.020P)2 + 0.652P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
4957 reflections | Δρmax = 1.78 e Å−3 |
252 parameters | Δρmin = −1.91 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 | |
C1 | 0.1854 (4) | 0.1312 (3) | 0.1675 (2) | 0.0131 (5) | |
C2 | −0.0337 (3) | −0.1441 (3) | 0.1472 (2) | 0.0134 (5) | |
C3 | −0.1219 (4) | 0.0805 (3) | 0.1303 (2) | 0.0143 (6) | |
C11 | 0.0637 (3) | 0.2422 (3) | 0.4379 (2) | 0.0090 (5) | |
C12 | 0.1205 (3) | 0.3743 (3) | 0.5326 (2) | 0.0089 (5) | |
C13 | 0.1932 (3) | 0.5189 (3) | 0.5164 (2) | 0.0112 (5) | |
H13 | 0.200584 | 0.529294 | 0.445278 | 0.013* | |
C14 | 0.2547 (4) | 0.6473 (3) | 0.6036 (2) | 0.0155 (6) | |
H14 | 0.304264 | 0.745532 | 0.592324 | 0.019* | |
C15 | 0.2437 (3) | 0.6319 (3) | 0.7075 (2) | 0.0158 (6) | |
H15 | 0.285682 | 0.719661 | 0.767527 | 0.019* | |
C16 | 0.1712 (3) | 0.4878 (3) | 0.7236 (2) | 0.0141 (5) | |
H16 | 0.163508 | 0.477699 | 0.794685 | 0.017* | |
C17 | 0.1099 (3) | 0.3586 (3) | 0.6367 (2) | 0.0108 (5) | |
H17 | 0.061047 | 0.260413 | 0.648235 | 0.013* | |
C21 | 0.5420 (4) | 0.3084 (3) | 0.6767 (2) | 0.0159 (6) | |
H21A | 0.621877 | 0.292673 | 0.650199 | 0.019* | |
H21B | 0.435037 | 0.217975 | 0.636214 | 0.019* | |
C22 | 0.5261 (4) | 0.4462 (4) | 0.6438 (3) | 0.0216 (7) | |
H22A | 0.469027 | 0.422069 | 0.561092 | 0.032* | |
H22B | 0.635206 | 0.531177 | 0.667625 | 0.032* | |
H22C | 0.463608 | 0.474617 | 0.681341 | 0.032* | |
C23 | 0.4561 (3) | 0.3052 (3) | 0.8386 (2) | 0.0132 (5) | |
H23A | 0.357021 | 0.212011 | 0.788158 | 0.016* | |
H23B | 0.433328 | 0.393035 | 0.826119 | 0.016* | |
C24 | 0.4852 (4) | 0.2995 (4) | 0.9611 (2) | 0.0211 (6) | |
H24A | 0.389219 | 0.291683 | 0.976247 | 0.032* | |
H24B | 0.581410 | 0.392365 | 1.012214 | 0.032* | |
H24C | 0.503936 | 0.210858 | 0.974056 | 0.032* | |
C25 | 0.7425 (3) | 0.4676 (3) | 0.8731 (2) | 0.0122 (5) | |
H25A | 0.775353 | 0.466013 | 0.954154 | 0.015* | |
H25B | 0.709086 | 0.550202 | 0.865005 | 0.015* | |
C26 | 0.8911 (3) | 0.5058 (3) | 0.8422 (2) | 0.0165 (6) | |
H26A | 0.925742 | 0.424985 | 0.849587 | 0.025* | |
H26B | 0.980649 | 0.602466 | 0.893561 | 0.025* | |
H26C | 0.862643 | 0.514604 | 0.763558 | 0.025* | |
C27 | 0.6407 (3) | 0.1891 (3) | 0.8242 (2) | 0.0143 (6) | |
H27A | 0.725049 | 0.196124 | 0.793807 | 0.017* | |
H27B | 0.689899 | 0.202742 | 0.907368 | 0.017* | |
C28 | 0.4989 (4) | 0.0316 (3) | 0.7716 (3) | 0.0222 (7) | |
H28A | 0.538413 | −0.044634 | 0.787962 | 0.033* | |
H28B | 0.449790 | 0.015995 | 0.689026 | 0.033* | |
H28C | 0.416609 | 0.021397 | 0.803624 | 0.033* | |
N1 | −0.0464 (3) | 0.1077 (2) | 0.43186 (18) | 0.0093 (4) | |
N2 | 0.5959 (3) | 0.3183 (2) | 0.80319 (17) | 0.0087 (4) | |
O1 | 0.2774 (3) | 0.1839 (2) | 0.12566 (18) | 0.0208 (5) | |
O2 | −0.0760 (3) | −0.2637 (2) | 0.09062 (17) | 0.0204 (5) | |
O3 | −0.2210 (3) | 0.0988 (2) | 0.06245 (18) | 0.0223 (5) | |
O11 | 0.1223 (2) | 0.2589 (2) | 0.36066 (15) | 0.0122 (4) | |
O12 | −0.0965 (2) | −0.0148 (2) | 0.34430 (15) | 0.0105 (4) | |
Br1 | 0.26528 (3) | 0.01265 (3) | 0.40365 (2) | 0.01252 (6) | |
Re1 | 0.03945 (2) | 0.05041 (2) | 0.24114 (2) | 0.00857 (4) | |
H1 | −0.093 (4) | 0.086 (4) | 0.483 (3) | 0.026 (10)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0205 (15) | 0.0112 (12) | 0.0077 (11) | 0.0075 (11) | 0.0051 (11) | 0.0023 (10) |
C2 | 0.0164 (14) | 0.0194 (14) | 0.0095 (12) | 0.0106 (11) | 0.0070 (11) | 0.0067 (11) |
C3 | 0.0189 (15) | 0.0098 (12) | 0.0110 (12) | 0.0029 (11) | 0.0069 (11) | 0.0012 (10) |
C11 | 0.0095 (12) | 0.0113 (12) | 0.0074 (11) | 0.0054 (10) | 0.0036 (10) | 0.0035 (9) |
C12 | 0.0081 (12) | 0.0095 (12) | 0.0089 (11) | 0.0039 (9) | 0.0038 (10) | 0.0000 (9) |
C13 | 0.0102 (13) | 0.0130 (12) | 0.0115 (12) | 0.0054 (10) | 0.0052 (10) | 0.0037 (10) |
C14 | 0.0161 (14) | 0.0113 (13) | 0.0165 (13) | 0.0044 (11) | 0.0057 (11) | 0.0018 (10) |
C15 | 0.0152 (14) | 0.0138 (13) | 0.0145 (13) | 0.0050 (11) | 0.0048 (11) | −0.0024 (10) |
C16 | 0.0125 (13) | 0.0187 (14) | 0.0109 (12) | 0.0056 (11) | 0.0066 (11) | 0.0017 (10) |
C17 | 0.0079 (12) | 0.0131 (12) | 0.0114 (12) | 0.0040 (10) | 0.0051 (10) | 0.0021 (10) |
C21 | 0.0162 (14) | 0.0218 (14) | 0.0055 (11) | 0.0048 (11) | 0.0040 (10) | 0.0021 (10) |
C22 | 0.0168 (15) | 0.0314 (17) | 0.0206 (15) | 0.0112 (13) | 0.0082 (12) | 0.0174 (13) |
C23 | 0.0087 (13) | 0.0168 (13) | 0.0148 (13) | 0.0048 (10) | 0.0068 (10) | 0.0030 (10) |
C24 | 0.0230 (16) | 0.0267 (16) | 0.0177 (14) | 0.0091 (13) | 0.0151 (13) | 0.0074 (12) |
C25 | 0.0100 (13) | 0.0108 (12) | 0.0094 (12) | 0.0007 (10) | 0.0019 (10) | −0.0010 (10) |
C26 | 0.0107 (13) | 0.0168 (14) | 0.0190 (14) | 0.0024 (11) | 0.0067 (11) | 0.0052 (11) |
C27 | 0.0136 (14) | 0.0111 (12) | 0.0172 (13) | 0.0057 (10) | 0.0045 (11) | 0.0041 (10) |
C28 | 0.0180 (15) | 0.0095 (13) | 0.0385 (18) | 0.0037 (11) | 0.0142 (14) | 0.0039 (12) |
N1 | 0.0109 (11) | 0.0095 (10) | 0.0067 (10) | 0.0036 (8) | 0.0044 (9) | 0.0002 (8) |
N2 | 0.0081 (11) | 0.0100 (10) | 0.0072 (10) | 0.0034 (8) | 0.0032 (8) | 0.0015 (8) |
O1 | 0.0271 (12) | 0.0249 (11) | 0.0216 (11) | 0.0143 (9) | 0.0180 (10) | 0.0122 (9) |
O2 | 0.0265 (12) | 0.0133 (10) | 0.0167 (10) | 0.0092 (9) | 0.0039 (9) | −0.0012 (8) |
O3 | 0.0241 (12) | 0.0253 (11) | 0.0177 (10) | 0.0133 (9) | 0.0044 (9) | 0.0100 (9) |
O11 | 0.0163 (10) | 0.0100 (9) | 0.0098 (9) | 0.0039 (7) | 0.0075 (8) | 0.0011 (7) |
O12 | 0.0120 (9) | 0.0067 (8) | 0.0086 (9) | 0.0004 (7) | 0.0049 (7) | −0.0022 (7) |
Br1 | 0.01056 (13) | 0.01808 (13) | 0.00890 (12) | 0.00574 (10) | 0.00462 (10) | 0.00339 (10) |
Re1 | 0.01144 (6) | 0.00867 (6) | 0.00553 (6) | 0.00374 (4) | 0.00431 (4) | 0.00140 (4) |
Geometric parameters (Å, º) top
C1—O1 | 1.159 (3) | C23—N2 | 1.517 (4) |
C1—Re1 | 1.905 (3) | C23—C24 | 1.518 (4) |
C2—O2 | 1.163 (3) | C23—H23A | 0.9900 |
C2—Re1 | 1.892 (3) | C23—H23B | 0.9900 |
C3—O3 | 1.157 (3) | C24—H24A | 0.9800 |
C3—Re1 | 1.889 (3) | C24—H24B | 0.9800 |
C11—O11 | 1.282 (3) | C24—H24C | 0.9800 |
C11—N1 | 1.314 (3) | C25—N2 | 1.510 (3) |
C11—C12 | 1.476 (4) | C25—C26 | 1.523 (4) |
C12—C17 | 1.391 (3) | C25—H25A | 0.9900 |
C12—C13 | 1.396 (3) | C25—H25B | 0.9900 |
C13—C14 | 1.384 (4) | C26—H26A | 0.9800 |
C13—H13 | 0.9500 | C26—H26B | 0.9800 |
C14—C15 | 1.389 (4) | C26—H26C | 0.9800 |
C14—H14 | 0.9500 | C27—C28 | 1.513 (4) |
C15—C16 | 1.390 (4) | C27—N2 | 1.521 (3) |
C15—H15 | 0.9500 | C27—H27A | 0.9900 |
C16—C17 | 1.388 (4) | C27—H27B | 0.9900 |
C16—H16 | 0.9500 | C28—H28A | 0.9800 |
C17—H17 | 0.9500 | C28—H28B | 0.9800 |
C21—C22 | 1.515 (4) | C28—H28C | 0.9800 |
C21—N2 | 1.518 (3) | N1—O12 | 1.373 (3) |
C21—H21A | 0.9900 | N1—H1 | 0.91 (4) |
C21—H21B | 0.9900 | O11—Re1 | 2.1292 (19) |
C22—H22A | 0.9800 | O12—Re1 | 2.1204 (19) |
C22—H22B | 0.9800 | Br1—Re1 | 2.6690 (5) |
C22—H22C | 0.9800 | | |
| | | |
O1—C1—Re1 | 177.9 (2) | N2—C25—H25A | 108.4 |
O2—C2—Re1 | 178.7 (3) | C26—C25—H25A | 108.4 |
O3—C3—Re1 | 179.9 (3) | N2—C25—H25B | 108.4 |
O11—C11—N1 | 119.6 (2) | C26—C25—H25B | 108.4 |
O11—C11—C12 | 119.6 (2) | H25A—C25—H25B | 107.5 |
N1—C11—C12 | 120.8 (2) | C25—C26—H26A | 109.5 |
C17—C12—C13 | 120.0 (2) | C25—C26—H26B | 109.5 |
C17—C12—C11 | 122.3 (2) | H26A—C26—H26B | 109.5 |
C13—C12—C11 | 117.6 (2) | C25—C26—H26C | 109.5 |
C14—C13—C12 | 120.3 (2) | H26A—C26—H26C | 109.5 |
C14—C13—H13 | 119.8 | H26B—C26—H26C | 109.5 |
C12—C13—H13 | 119.8 | C28—C27—N2 | 114.7 (2) |
C13—C14—C15 | 119.8 (2) | C28—C27—H27A | 108.6 |
C13—C14—H14 | 120.1 | N2—C27—H27A | 108.6 |
C15—C14—H14 | 120.1 | C28—C27—H27B | 108.6 |
C14—C15—C16 | 119.9 (3) | N2—C27—H27B | 108.6 |
C14—C15—H15 | 120.0 | H27A—C27—H27B | 107.6 |
C16—C15—H15 | 120.0 | C27—C28—H28A | 109.5 |
C17—C16—C15 | 120.6 (3) | C27—C28—H28B | 109.5 |
C17—C16—H16 | 119.7 | H28A—C28—H28B | 109.5 |
C15—C16—H16 | 119.7 | C27—C28—H28C | 109.5 |
C16—C17—C12 | 119.4 (2) | H28A—C28—H28C | 109.5 |
C16—C17—H17 | 120.3 | H28B—C28—H28C | 109.5 |
C12—C17—H17 | 120.3 | C11—N1—O12 | 120.2 (2) |
C22—C21—N2 | 115.0 (2) | C11—N1—H1 | 125 (2) |
C22—C21—H21A | 108.5 | O12—N1—H1 | 114 (2) |
N2—C21—H21A | 108.5 | C25—N2—C23 | 108.3 (2) |
C22—C21—H21B | 108.5 | C25—N2—C21 | 111.85 (19) |
N2—C21—H21B | 108.5 | C23—N2—C21 | 108.7 (2) |
H21A—C21—H21B | 107.5 | C25—N2—C27 | 109.0 (2) |
C21—C22—H22A | 109.5 | C23—N2—C27 | 111.0 (2) |
C21—C22—H22B | 109.5 | C21—N2—C27 | 108.1 (2) |
H22A—C22—H22B | 109.5 | C11—O11—Re1 | 113.20 (16) |
C21—C22—H22C | 109.5 | N1—O12—Re1 | 109.83 (14) |
H22A—C22—H22C | 109.5 | C3—Re1—C2 | 89.93 (12) |
H22B—C22—H22C | 109.5 | C3—Re1—C1 | 89.58 (12) |
N2—C23—C24 | 115.2 (2) | C2—Re1—C1 | 88.02 (12) |
N2—C23—H23A | 108.5 | C3—Re1—O12 | 94.96 (10) |
C24—C23—H23A | 108.5 | C2—Re1—O12 | 98.84 (10) |
N2—C23—H23B | 108.5 | C1—Re1—O12 | 171.76 (9) |
C24—C23—H23B | 108.5 | C3—Re1—O11 | 94.10 (10) |
H23A—C23—H23B | 107.5 | C2—Re1—O11 | 174.27 (8) |
C23—C24—H24A | 109.5 | C1—Re1—O11 | 96.07 (9) |
C23—C24—H24B | 109.5 | O12—Re1—O11 | 76.78 (7) |
H24A—C24—H24B | 109.5 | C3—Re1—Br1 | 177.92 (9) |
C23—C24—H24C | 109.5 | C2—Re1—Br1 | 91.65 (8) |
H24A—C24—H24C | 109.5 | C1—Re1—Br1 | 91.82 (8) |
H24B—C24—H24C | 109.5 | O12—Re1—Br1 | 83.47 (5) |
N2—C25—C26 | 115.5 (2) | O11—Re1—Br1 | 84.23 (5) |
| | | |
O11—C11—C12—C17 | −156.9 (3) | C26—C25—N2—C21 | −55.6 (3) |
N1—C11—C12—C17 | 23.2 (4) | C26—C25—N2—C27 | 63.9 (3) |
O11—C11—C12—C13 | 20.4 (4) | C24—C23—N2—C25 | −63.3 (3) |
N1—C11—C12—C13 | −159.5 (2) | C24—C23—N2—C21 | 175.0 (2) |
C17—C12—C13—C14 | −0.1 (4) | C24—C23—N2—C27 | 56.3 (3) |
C11—C12—C13—C14 | −177.5 (3) | C22—C21—N2—C25 | −48.1 (3) |
C12—C13—C14—C15 | −0.1 (4) | C22—C21—N2—C23 | 71.4 (3) |
C13—C14—C15—C16 | 0.0 (4) | C22—C21—N2—C27 | −168.1 (2) |
C14—C15—C16—C17 | 0.2 (4) | C28—C27—N2—C25 | 172.4 (2) |
C15—C16—C17—C12 | −0.4 (4) | C28—C27—N2—C23 | 53.3 (3) |
C13—C12—C17—C16 | 0.4 (4) | C28—C27—N2—C21 | −65.8 (3) |
C11—C12—C17—C16 | 177.6 (3) | N1—C11—O11—Re1 | −5.3 (3) |
O11—C11—N1—O12 | 1.1 (4) | C12—C11—O11—Re1 | 174.80 (18) |
C12—C11—N1—O12 | −179.0 (2) | C11—N1—O12—Re1 | 3.7 (3) |
C26—C25—N2—C23 | −175.3 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···Br1i | 0.91 (4) | 2.52 (4) | 3.420 (2) | 170 (3) |
C23—H23A···O12i | 0.99 | 2.41 | 3.388 (3) | 170 |
C25—H25B···O1ii | 0.99 | 2.57 | 3.520 (4) | 162 |
C26—H26A···O2iii | 0.98 | 2.56 | 3.520 (4) | 166 |
C27—H27B···O3iv | 0.99 | 2.40 | 3.286 (3) | 149 |
C17—H17···O12i | 0.95 | 2.59 | 3.385 (3) | 142 |
C25—H25A···O2v | 0.99 | 2.59 | 3.111 (3) | 113 |
Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y, −z+1; (iv) x+1, y, z+1; (v) x+1, y+1, z+1. |
fac-Aquatricarbonyl(4-oxo-2-phenylchromen-3-olato-\
κ2O,
O')rhenium(I)–3-hydroxyflavone (1/1) (10Amsc4)
top
Crystal data top
[Re(C15H9O3)(CO)3(H2O)]·C15H10O3 | Z = 2 |
Mr = 763.70 | F(000) = 748 |
Triclinic, P1 | Dx = 1.864 Mg m−3 |
a = 10.5209 (15) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.9365 (17) Å | Cell parameters from 9860 reflections |
c = 12.4455 (17) Å | θ = 2.9–28.6° |
α = 108.277 (7)° | µ = 4.53 mm−1 |
β = 102.745 (7)° | T = 100 K |
γ = 104.252 (7)° | Cuboid, yellow |
V = 1361.0 (3) Å3 | 0.55 × 0.17 × 0.08 mm |
Data collection top
Bruker APEXII CCD diffractometer | 6045 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.038 |
φ and ω scans | θmax = 28.6°, θmin = 3.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −14→14 |
Tmin = 0.417, Tmax = 0.699 | k = −16→16 |
23222 measured reflections | l = −16→16 |
6700 independent reflections | |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.027 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.060 | w = 1/[σ2(Fo2) + (0.0156P)2 + 3.4093P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
6700 reflections | Δρmax = 1.40 e Å−3 |
406 parameters | Δρmin = −2.10 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 | |
C1 | 0.5140 (4) | −0.2364 (3) | 0.4055 (3) | 0.0199 (7) | |
C2 | 0.3810 (4) | −0.2744 (3) | 0.1859 (3) | 0.0204 (7) | |
C3 | 0.6494 (4) | −0.2215 (3) | 0.2549 (3) | 0.0196 (7) | |
C11 | 0.6247 (4) | 0.0961 (3) | 0.2846 (3) | 0.0198 (7) | |
C011 | 0.2049 (3) | −0.0071 (3) | 1.1005 (3) | 0.0202 (7) | |
C012 | 0.1389 (3) | −0.0859 (3) | 0.9754 (3) | 0.0192 (7) | |
C12 | 0.6965 (4) | 0.1271 (3) | 0.4072 (3) | 0.0190 (7) | |
C013 | 0.1113 (3) | −0.0380 (3) | 0.8907 (3) | 0.0175 (7) | |
C13 | 0.7720 (4) | 0.2509 (3) | 0.4809 (3) | 0.0189 (7) | |
C21 | 0.7148 (4) | 0.3169 (3) | 0.3205 (3) | 0.0209 (7) | |
C021 | 0.2151 (3) | 0.1691 (3) | 1.0409 (3) | 0.0189 (7) | |
C22 | 0.7313 (4) | 0.4166 (3) | 0.2842 (3) | 0.0239 (8) | |
H22 | 0.787106 | 0.499269 | 0.339470 | 0.029* | |
C022 | 0.2528 (4) | 0.2964 (3) | 1.0638 (3) | 0.0229 (7) | |
H022 | 0.232380 | 0.324554 | 1.000692 | 0.027* | |
C23 | 0.6658 (4) | 0.3942 (4) | 0.1671 (3) | 0.0255 (8) | |
H23 | 0.676381 | 0.461921 | 0.141326 | 0.031* | |
C023 | 0.3209 (4) | 0.3812 (4) | 1.1806 (3) | 0.0252 (8) | |
H023 | 0.347574 | 0.468651 | 1.198032 | 0.030* | |
C24 | 0.5831 (4) | 0.2715 (4) | 0.0852 (3) | 0.0227 (7) | |
H24 | 0.537225 | 0.256493 | 0.004552 | 0.027* | |
C024 | 0.3510 (4) | 0.3394 (4) | 1.2738 (3) | 0.0261 (8) | |
H024 | 0.397856 | 0.398781 | 1.353607 | 0.031* | |
C025 | 0.3136 (4) | 0.2146 (4) | 1.2504 (3) | 0.0230 (8) | |
H025 | 0.333851 | 0.186976 | 1.313909 | 0.028* | |
C25 | 0.5693 (4) | 0.1744 (3) | 0.1224 (3) | 0.0195 (7) | |
H25 | 0.513423 | 0.091696 | 0.067187 | 0.023* | |
C026 | 0.2446 (3) | 0.1261 (3) | 1.1318 (3) | 0.0187 (7) | |
C26 | 0.6363 (4) | 0.1949 (3) | 0.2411 (3) | 0.0194 (7) | |
C31 | 0.8486 (3) | 0.3033 (3) | 0.6094 (3) | 0.0186 (7) | |
C031 | 0.0386 (3) | −0.1072 (3) | 0.7614 (3) | 0.0184 (7) | |
C32 | 0.9040 (4) | 0.2321 (3) | 0.6644 (3) | 0.0211 (7) | |
H32 | 0.887587 | 0.146275 | 0.619442 | 0.025* | |
C032 | 0.0070 (4) | −0.2361 (3) | 0.7066 (3) | 0.0225 (7) | |
H032 | 0.036121 | −0.281227 | 0.752195 | 0.027* | |
C033 | −0.0667 (4) | −0.2990 (4) | 0.5857 (3) | 0.0267 (8) | |
H033 | −0.086890 | −0.386934 | 0.549063 | 0.032* | |
C33 | 0.9827 (4) | 0.2869 (3) | 0.7842 (3) | 0.0220 (7) | |
H33 | 1.020553 | 0.238159 | 0.820573 | 0.026* | |
C034 | −0.1115 (4) | −0.2356 (4) | 0.5174 (3) | 0.0242 (8) | |
H034 | −0.164075 | −0.279874 | 0.435007 | 0.029* | |
C34 | 1.0072 (4) | 0.4102 (4) | 0.8516 (3) | 0.0231 (7) | |
H34 | 1.063253 | 0.447020 | 0.933291 | 0.028* | |
C35 | 0.9494 (4) | 0.4802 (3) | 0.7994 (3) | 0.0238 (8) | |
H35 | 0.963214 | 0.564889 | 0.846217 | 0.029* | |
C035 | −0.0788 (4) | −0.1076 (4) | 0.5705 (3) | 0.0272 (8) | |
H035 | −0.108130 | −0.063143 | 0.524232 | 0.033* | |
C36 | 0.8714 (4) | 0.4280 (3) | 0.6793 (3) | 0.0211 (7) | |
H36 | 0.833146 | 0.477405 | 0.644207 | 0.025* | |
C036 | −0.0031 (4) | −0.0433 (3) | 0.6912 (3) | 0.0249 (8) | |
H036 | 0.020503 | 0.045221 | 0.726428 | 0.030* | |
O1 | 0.5028 (3) | −0.2981 (3) | 0.4610 (2) | 0.0277 (6) | |
O2 | 0.2923 (3) | −0.3565 (3) | 0.1074 (2) | 0.0297 (6) | |
O3 | 0.7187 (3) | −0.2755 (3) | 0.2184 (2) | 0.0305 (6) | |
O04 | 0.2208 (3) | −0.0595 (2) | 1.1723 (2) | 0.0242 (5) | |
O4 | 0.5511 (3) | −0.0166 (2) | 0.2184 (2) | 0.0210 (5) | |
O5 | 0.6847 (2) | 0.0325 (2) | 0.4444 (2) | 0.0191 (5) | |
O05 | 0.1030 (3) | −0.2108 (2) | 0.9494 (2) | 0.0250 (6) | |
H05 | 0.132731 | −0.222694 | 1.011772 | 0.038* | |
O6 | 0.7796 (2) | 0.3434 (2) | 0.4386 (2) | 0.0200 (5) | |
O06 | 0.1490 (2) | 0.0888 (2) | 0.9236 (2) | 0.0191 (5) | |
O7 | 0.4034 (3) | −0.0289 (2) | 0.3719 (3) | 0.0209 (6) | |
Re1 | 0.53064 (2) | −0.13900 (2) | 0.31117 (2) | 0.01536 (4) | |
H7A | 0.354 (5) | −0.031 (4) | 0.329 (4) | 0.021 (13)* | |
H7B | 0.369 (5) | −0.047 (5) | 0.425 (5) | 0.045 (15)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0201 (17) | 0.0165 (17) | 0.0177 (16) | 0.0051 (14) | 0.0020 (14) | 0.0035 (14) |
C2 | 0.0226 (17) | 0.0241 (19) | 0.0163 (16) | 0.0082 (15) | 0.0088 (14) | 0.0082 (15) |
C3 | 0.0207 (17) | 0.0171 (17) | 0.0152 (16) | 0.0029 (14) | 0.0020 (13) | 0.0042 (13) |
C11 | 0.0214 (17) | 0.0195 (18) | 0.0183 (16) | 0.0087 (14) | 0.0062 (14) | 0.0059 (14) |
C011 | 0.0151 (15) | 0.0267 (19) | 0.0200 (17) | 0.0096 (14) | 0.0048 (13) | 0.0093 (15) |
C012 | 0.0150 (15) | 0.0181 (17) | 0.0227 (17) | 0.0053 (13) | 0.0035 (13) | 0.0079 (14) |
C12 | 0.0196 (16) | 0.0160 (17) | 0.0209 (17) | 0.0071 (14) | 0.0071 (14) | 0.0052 (14) |
C013 | 0.0144 (15) | 0.0161 (16) | 0.0205 (16) | 0.0058 (13) | 0.0037 (13) | 0.0061 (14) |
C13 | 0.0195 (16) | 0.0185 (17) | 0.0190 (16) | 0.0065 (14) | 0.0056 (14) | 0.0083 (14) |
C21 | 0.0230 (17) | 0.0227 (19) | 0.0166 (16) | 0.0097 (15) | 0.0053 (14) | 0.0065 (14) |
C021 | 0.0153 (15) | 0.0223 (18) | 0.0162 (16) | 0.0079 (14) | 0.0024 (13) | 0.0046 (14) |
C22 | 0.0291 (19) | 0.0166 (18) | 0.0224 (18) | 0.0058 (15) | 0.0042 (15) | 0.0073 (15) |
C022 | 0.0229 (17) | 0.0210 (18) | 0.0214 (17) | 0.0101 (15) | 0.0020 (14) | 0.0056 (15) |
C23 | 0.0298 (19) | 0.024 (2) | 0.0246 (19) | 0.0094 (16) | 0.0070 (16) | 0.0137 (16) |
C023 | 0.0240 (18) | 0.0202 (19) | 0.0258 (19) | 0.0077 (15) | 0.0037 (15) | 0.0048 (15) |
C24 | 0.0245 (18) | 0.029 (2) | 0.0170 (17) | 0.0115 (16) | 0.0072 (14) | 0.0105 (15) |
C024 | 0.0242 (18) | 0.026 (2) | 0.0190 (17) | 0.0084 (16) | 0.0004 (15) | 0.0012 (15) |
C025 | 0.0188 (17) | 0.029 (2) | 0.0176 (17) | 0.0073 (15) | 0.0026 (14) | 0.0080 (15) |
C25 | 0.0203 (16) | 0.0205 (18) | 0.0170 (16) | 0.0080 (14) | 0.0050 (14) | 0.0061 (14) |
C026 | 0.0136 (15) | 0.0217 (18) | 0.0192 (16) | 0.0067 (13) | 0.0037 (13) | 0.0066 (14) |
C26 | 0.0189 (16) | 0.0214 (18) | 0.0184 (16) | 0.0073 (14) | 0.0063 (14) | 0.0081 (14) |
C31 | 0.0165 (16) | 0.0184 (17) | 0.0166 (16) | 0.0040 (13) | 0.0029 (13) | 0.0045 (14) |
C031 | 0.0163 (15) | 0.0216 (18) | 0.0185 (16) | 0.0083 (14) | 0.0047 (13) | 0.0088 (14) |
C32 | 0.0205 (17) | 0.0176 (18) | 0.0196 (17) | 0.0078 (14) | 0.0012 (14) | 0.0027 (14) |
C032 | 0.0256 (18) | 0.0202 (18) | 0.0219 (18) | 0.0081 (15) | 0.0056 (15) | 0.0095 (15) |
C033 | 0.036 (2) | 0.0195 (19) | 0.0204 (18) | 0.0080 (16) | 0.0051 (16) | 0.0064 (15) |
C33 | 0.0193 (17) | 0.0253 (19) | 0.0186 (17) | 0.0075 (15) | 0.0017 (14) | 0.0081 (15) |
C034 | 0.0283 (19) | 0.0232 (19) | 0.0157 (16) | 0.0066 (15) | 0.0026 (15) | 0.0052 (14) |
C34 | 0.0191 (17) | 0.028 (2) | 0.0192 (17) | 0.0053 (15) | 0.0049 (14) | 0.0077 (15) |
C35 | 0.0284 (19) | 0.0151 (17) | 0.0214 (18) | 0.0009 (15) | 0.0058 (15) | 0.0053 (14) |
C035 | 0.037 (2) | 0.026 (2) | 0.0187 (17) | 0.0150 (17) | 0.0029 (16) | 0.0100 (16) |
C36 | 0.0264 (18) | 0.0156 (17) | 0.0191 (17) | 0.0072 (14) | 0.0046 (14) | 0.0057 (14) |
C036 | 0.032 (2) | 0.0180 (18) | 0.0221 (18) | 0.0109 (16) | 0.0043 (16) | 0.0064 (15) |
O1 | 0.0321 (14) | 0.0296 (15) | 0.0262 (14) | 0.0114 (12) | 0.0075 (12) | 0.0176 (12) |
O2 | 0.0269 (14) | 0.0269 (15) | 0.0207 (13) | −0.0043 (12) | 0.0038 (11) | 0.0039 (12) |
O3 | 0.0307 (14) | 0.0344 (16) | 0.0299 (15) | 0.0169 (13) | 0.0121 (12) | 0.0107 (13) |
O04 | 0.0247 (13) | 0.0261 (14) | 0.0215 (13) | 0.0077 (11) | 0.0019 (11) | 0.0134 (11) |
O4 | 0.0252 (13) | 0.0185 (13) | 0.0187 (12) | 0.0080 (10) | 0.0052 (10) | 0.0072 (10) |
O5 | 0.0207 (12) | 0.0169 (12) | 0.0150 (11) | 0.0052 (10) | 0.0016 (10) | 0.0041 (10) |
O05 | 0.0311 (14) | 0.0188 (13) | 0.0213 (13) | 0.0075 (11) | 0.0003 (11) | 0.0093 (11) |
O6 | 0.0238 (12) | 0.0134 (12) | 0.0175 (12) | 0.0034 (10) | 0.0008 (10) | 0.0054 (10) |
O06 | 0.0202 (12) | 0.0164 (12) | 0.0169 (11) | 0.0067 (10) | 0.0006 (10) | 0.0049 (10) |
O7 | 0.0211 (13) | 0.0229 (14) | 0.0177 (13) | 0.0105 (11) | 0.0016 (12) | 0.0079 (11) |
Re1 | 0.01730 (7) | 0.01368 (7) | 0.01221 (7) | 0.00484 (5) | 0.00184 (5) | 0.00370 (5) |
Geometric parameters (Å, º) top
C1—O1 | 1.160 (4) | C24—H24 | 0.9500 |
C1—Re1 | 1.900 (4) | C024—C025 | 1.360 (5) |
C2—O2 | 1.154 (4) | C024—H024 | 0.9500 |
C2—Re1 | 1.899 (4) | C025—C026 | 1.412 (5) |
C3—O3 | 1.161 (4) | C025—H025 | 0.9500 |
C3—Re1 | 1.892 (4) | C25—C26 | 1.403 (5) |
C11—O4 | 1.265 (4) | C25—H25 | 0.9500 |
C11—C12 | 1.426 (5) | C31—C36 | 1.397 (5) |
C11—C26 | 1.433 (5) | C31—C32 | 1.400 (5) |
C011—O04 | 1.246 (4) | C031—C032 | 1.390 (5) |
C011—C026 | 1.438 (5) | C031—C036 | 1.398 (5) |
C011—C012 | 1.441 (5) | C32—C33 | 1.384 (5) |
C012—O05 | 1.354 (4) | C32—H32 | 0.9500 |
C012—C013 | 1.359 (5) | C032—C033 | 1.385 (5) |
C12—O5 | 1.338 (4) | C032—H032 | 0.9500 |
C12—C13 | 1.380 (5) | C033—C034 | 1.385 (5) |
C013—O06 | 1.364 (4) | C033—H033 | 0.9500 |
C013—C031 | 1.473 (5) | C33—C34 | 1.370 (5) |
C13—O6 | 1.357 (4) | C33—H33 | 0.9500 |
C13—C31 | 1.468 (5) | C034—C035 | 1.377 (5) |
C21—O6 | 1.373 (4) | C034—H034 | 0.9500 |
C21—C22 | 1.385 (5) | C34—C35 | 1.381 (5) |
C21—C26 | 1.388 (5) | C34—H34 | 0.9500 |
C021—O06 | 1.371 (4) | C35—C36 | 1.385 (5) |
C021—C022 | 1.389 (5) | C35—H35 | 0.9500 |
C021—C026 | 1.389 (5) | C035—C036 | 1.388 (5) |
C22—C23 | 1.376 (5) | C035—H035 | 0.9500 |
C22—H22 | 0.9500 | C36—H36 | 0.9500 |
C022—C023 | 1.383 (5) | C036—H036 | 0.9500 |
C022—H022 | 0.9500 | O4—Re1 | 2.128 (2) |
C23—C24 | 1.410 (5) | O5—Re1 | 2.149 (2) |
C23—H23 | 0.9500 | O05—H05 | 0.8400 |
C023—C024 | 1.404 (5) | O7—Re1 | 2.187 (3) |
C023—H023 | 0.9500 | O7—H7A | 0.65 (4) |
C24—C25 | 1.366 (5) | O7—H7B | 0.87 (5) |
| | | |
O1—C1—Re1 | 178.6 (3) | C36—C31—C13 | 120.0 (3) |
O2—C2—Re1 | 177.9 (3) | C32—C31—C13 | 121.6 (3) |
O3—C3—Re1 | 177.9 (3) | C032—C031—C036 | 118.4 (3) |
O4—C11—C12 | 119.3 (3) | C032—C031—C013 | 121.8 (3) |
O4—C11—C26 | 122.1 (3) | C036—C031—C013 | 119.7 (3) |
C12—C11—C26 | 118.6 (3) | C33—C32—C31 | 119.9 (3) |
O04—C011—C026 | 125.6 (3) | C33—C32—H32 | 120.1 |
O04—C011—C012 | 117.7 (3) | C31—C32—H32 | 120.1 |
C026—C011—C012 | 116.7 (3) | C033—C032—C031 | 120.2 (3) |
O05—C012—C013 | 122.8 (3) | C033—C032—H032 | 119.9 |
O05—C012—C011 | 115.0 (3) | C031—C032—H032 | 119.9 |
C013—C012—C011 | 122.2 (3) | C032—C033—C034 | 121.0 (3) |
O5—C12—C13 | 123.6 (3) | C032—C033—H033 | 119.5 |
O5—C12—C11 | 117.0 (3) | C034—C033—H033 | 119.5 |
C13—C12—C11 | 119.4 (3) | C34—C33—C32 | 121.4 (3) |
C012—C013—O06 | 119.6 (3) | C34—C33—H33 | 119.3 |
C012—C013—C031 | 127.9 (3) | C32—C33—H33 | 119.3 |
O06—C013—C031 | 112.5 (3) | C035—C034—C033 | 119.1 (3) |
O6—C13—C12 | 121.1 (3) | C035—C034—H034 | 120.4 |
O6—C13—C31 | 110.7 (3) | C033—C034—H034 | 120.4 |
C12—C13—C31 | 128.1 (3) | C33—C34—C35 | 119.3 (3) |
O6—C21—C22 | 117.4 (3) | C33—C34—H34 | 120.4 |
O6—C21—C26 | 121.0 (3) | C35—C34—H34 | 120.4 |
C22—C21—C26 | 121.6 (3) | C34—C35—C36 | 120.5 (3) |
O06—C021—C022 | 116.3 (3) | C34—C35—H35 | 119.8 |
O06—C021—C026 | 122.1 (3) | C36—C35—H35 | 119.8 |
C022—C021—C026 | 121.6 (3) | C034—C035—C036 | 120.4 (3) |
C23—C22—C21 | 119.1 (3) | C034—C035—H035 | 119.8 |
C23—C22—H22 | 120.4 | C036—C035—H035 | 119.8 |
C21—C22—H22 | 120.4 | C35—C36—C31 | 120.6 (3) |
C023—C022—C021 | 118.4 (3) | C35—C36—H36 | 119.7 |
C023—C022—H022 | 120.8 | C31—C36—H36 | 119.7 |
C021—C022—H022 | 120.8 | C035—C036—C031 | 120.8 (3) |
C22—C23—C24 | 120.4 (3) | C035—C036—H036 | 119.6 |
C22—C23—H23 | 119.8 | C031—C036—H036 | 119.6 |
C24—C23—H23 | 119.8 | C11—O4—Re1 | 114.1 (2) |
C022—C023—C024 | 120.7 (4) | C12—O5—Re1 | 111.7 (2) |
C022—C023—H023 | 119.6 | C012—O05—H05 | 109.5 |
C024—C023—H023 | 119.6 | C13—O6—C21 | 121.2 (3) |
C25—C24—C23 | 119.6 (3) | C013—O06—C021 | 121.1 (3) |
C25—C24—H24 | 120.2 | Re1—O7—H7A | 114 (4) |
C23—C24—H24 | 120.2 | Re1—O7—H7B | 114 (3) |
C025—C024—C023 | 120.4 (3) | H7A—O7—H7B | 110 (5) |
C025—C024—H024 | 119.8 | C3—Re1—C2 | 87.10 (15) |
C023—C024—H024 | 119.8 | C3—Re1—C1 | 87.17 (15) |
C024—C025—C026 | 120.0 (3) | C2—Re1—C1 | 87.16 (15) |
C024—C025—H025 | 120.0 | C3—Re1—O4 | 96.33 (13) |
C026—C025—H025 | 120.0 | C2—Re1—O4 | 96.34 (12) |
C24—C25—C26 | 121.0 (3) | C1—Re1—O4 | 175.16 (12) |
C24—C25—H25 | 119.5 | C3—Re1—O5 | 98.98 (12) |
C26—C25—H25 | 119.5 | C2—Re1—O5 | 171.17 (12) |
C021—C026—C025 | 118.8 (3) | C1—Re1—O5 | 99.46 (12) |
C021—C026—C011 | 118.3 (3) | O4—Re1—O5 | 76.72 (9) |
C025—C026—C011 | 122.9 (3) | C3—Re1—O7 | 174.51 (13) |
C21—C26—C25 | 118.3 (3) | C2—Re1—O7 | 95.38 (13) |
C21—C26—C11 | 118.7 (3) | C1—Re1—O7 | 97.83 (13) |
C25—C26—C11 | 123.0 (3) | O4—Re1—O7 | 78.55 (10) |
C36—C31—C32 | 118.4 (3) | O5—Re1—O7 | 78.02 (10) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O7—H7A···O04i | 0.65 (4) | 2.00 (5) | 2.641 (4) | 167 (5) |
O7—H7B···O5ii | 0.87 (5) | 1.81 (6) | 2.658 (4) | 162 (5) |
O05—H05···O04 | 0.84 | 2.12 | 2.595 (4) | 115 |
C036—H036···O06 | 0.95 | 2.35 | 2.696 (4) | 101 |
C032—H032···O05 | 0.95 | 2.21 | 2.859 (4) | 125 |
C32—H32···O5 | 0.95 | 2.41 | 2.985 (4) | 119 |
C35—H35···O05iii | 0.95 | 2.46 | 3.334 (4) | 153 |
Symmetry codes: (i) x, y, z−1; (ii) −x+1, −y, −z+1; (iii) x+1, y+1, z. |
2-Phenylchromen-4-one (10RMSc3)
top
Crystal data top
C15H10O3 | Dx = 1.442 Mg m−3 |
Mr = 238.23 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 6732 reflections |
a = 5.3502 (6) Å | θ = 2.9–28.2° |
b = 11.3531 (14) Å | µ = 0.10 mm−1 |
c = 18.063 (2) Å | T = 100 K |
V = 1097.2 (2) Å3 | Cuboid, colourless |
Z = 4 | 0.37 × 0.17 × 0.15 mm |
F(000) = 496 | |
Data collection top
Bruker APEXII CCD diffractometer | 2376 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.033 |
φ and ω scans | θmax = 28.0°, θmin = 3.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −7→7 |
Tmin = 0.980, Tmax = 0.985 | k = −14→14 |
17120 measured reflections | l = −23→23 |
2621 independent reflections | |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.034 | w = 1/[σ2(Fo2) + (0.0394P)2 + 0.260P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.084 | (Δ/σ)max < 0.001 |
S = 1.07 | Δρmax = 0.21 e Å−3 |
2621 reflections | Δρmin = −0.21 e Å−3 |
165 parameters | Absolute structure: Refined as an inversion twin |
0 restraints | Absolute structure parameter: −0.5 (12) |
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. |
Refinement. Refined as a 2-component inversion twin |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C11 | 0.1494 (3) | 0.89389 (16) | 0.55141 (10) | 0.0162 (4) | |
C12 | −0.0276 (3) | 0.89383 (16) | 0.61248 (10) | 0.0163 (4) | |
C13 | −0.0335 (3) | 0.98193 (15) | 0.66332 (10) | 0.0164 (4) | |
C21 | 0.3073 (3) | 1.07756 (16) | 0.60398 (10) | 0.0174 (4) | |
C22 | 0.4691 (4) | 1.17374 (17) | 0.60567 (11) | 0.0203 (4) | |
H22 | 0.452871 | 1.232550 | 0.642778 | 0.024* | |
C23 | 0.6529 (4) | 1.18193 (17) | 0.55248 (11) | 0.0222 (4) | |
H23 | 0.763964 | 1.247233 | 0.552763 | 0.027* | |
C24 | 0.6776 (4) | 1.09508 (17) | 0.49812 (11) | 0.0215 (4) | |
H24 | 0.805645 | 1.101408 | 0.461886 | 0.026* | |
C25 | 0.5170 (3) | 1.00045 (17) | 0.49696 (10) | 0.0189 (4) | |
H25 | 0.534973 | 0.941415 | 0.460064 | 0.023* | |
C26 | 0.3258 (3) | 0.99081 (16) | 0.55035 (10) | 0.0172 (4) | |
C31 | −0.2061 (3) | 0.99745 (17) | 0.72618 (10) | 0.0176 (4) | |
C32 | −0.4076 (4) | 0.92170 (17) | 0.73825 (10) | 0.0192 (4) | |
H32 | −0.430858 | 0.855244 | 0.707050 | 0.023* | |
C33 | −0.5745 (4) | 0.94314 (18) | 0.79582 (11) | 0.0215 (4) | |
H33 | −0.712023 | 0.891625 | 0.803382 | 0.026* | |
C34 | −0.5413 (4) | 1.03891 (18) | 0.84203 (11) | 0.0225 (4) | |
H34 | −0.657024 | 1.053599 | 0.880846 | 0.027* | |
C35 | −0.3390 (4) | 1.11355 (18) | 0.83171 (11) | 0.0237 (4) | |
H35 | −0.314463 | 1.178438 | 0.864116 | 0.028* | |
C36 | −0.1722 (4) | 1.09365 (17) | 0.77409 (10) | 0.0203 (4) | |
H36 | −0.034600 | 1.145332 | 0.767048 | 0.024* | |
O4 | 0.1397 (2) | 0.81458 (11) | 0.50448 (7) | 0.0202 (3) | |
O5 | −0.1881 (3) | 0.80217 (12) | 0.61550 (7) | 0.0204 (3) | |
H5 | −0.193023 | 0.768617 | 0.574078 | 0.031* | |
O6 | 0.1319 (2) | 1.07378 (11) | 0.65851 (7) | 0.0182 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C11 | 0.0176 (9) | 0.0150 (9) | 0.0159 (9) | 0.0034 (7) | −0.0022 (7) | 0.0001 (7) |
C12 | 0.0180 (9) | 0.0148 (9) | 0.0161 (9) | −0.0008 (7) | −0.0027 (7) | 0.0017 (7) |
C13 | 0.0183 (8) | 0.0137 (9) | 0.0170 (9) | 0.0003 (7) | −0.0019 (7) | 0.0015 (7) |
C21 | 0.0184 (9) | 0.0161 (9) | 0.0176 (9) | 0.0014 (7) | −0.0014 (7) | 0.0033 (8) |
C22 | 0.0223 (10) | 0.0151 (9) | 0.0234 (10) | −0.0005 (7) | −0.0035 (8) | 0.0004 (8) |
C23 | 0.0208 (9) | 0.0183 (9) | 0.0274 (10) | −0.0022 (8) | −0.0020 (8) | 0.0050 (8) |
C24 | 0.0181 (9) | 0.0237 (10) | 0.0227 (10) | 0.0013 (8) | 0.0008 (8) | 0.0044 (8) |
C25 | 0.0195 (9) | 0.0183 (9) | 0.0189 (9) | 0.0037 (8) | 0.0000 (7) | 0.0009 (8) |
C26 | 0.0184 (9) | 0.0157 (9) | 0.0175 (9) | 0.0024 (7) | −0.0023 (7) | 0.0021 (7) |
C31 | 0.0199 (8) | 0.0165 (9) | 0.0163 (9) | 0.0046 (7) | −0.0018 (7) | 0.0013 (7) |
C32 | 0.0220 (9) | 0.0167 (9) | 0.0188 (9) | 0.0017 (7) | −0.0023 (7) | 0.0009 (8) |
C33 | 0.0221 (10) | 0.0209 (10) | 0.0217 (10) | 0.0032 (8) | 0.0005 (7) | 0.0033 (8) |
C34 | 0.0248 (9) | 0.0245 (10) | 0.0184 (9) | 0.0088 (8) | 0.0024 (7) | 0.0009 (8) |
C35 | 0.0280 (10) | 0.0232 (10) | 0.0198 (10) | 0.0063 (8) | −0.0022 (8) | −0.0045 (8) |
C36 | 0.0226 (9) | 0.0184 (10) | 0.0198 (10) | 0.0005 (7) | −0.0026 (7) | −0.0007 (7) |
O4 | 0.0233 (7) | 0.0181 (7) | 0.0190 (7) | 0.0000 (5) | 0.0006 (5) | −0.0044 (5) |
O5 | 0.0245 (7) | 0.0181 (7) | 0.0187 (7) | −0.0053 (6) | 0.0025 (5) | −0.0046 (5) |
O6 | 0.0218 (6) | 0.0146 (6) | 0.0184 (7) | −0.0027 (5) | 0.0010 (5) | −0.0028 (5) |
Geometric parameters (Å, º) top
C11—O4 | 1.238 (2) | C24—H24 | 0.9500 |
C11—C26 | 1.450 (3) | C25—C26 | 1.410 (3) |
C11—C12 | 1.454 (2) | C25—H25 | 0.9500 |
C12—O5 | 1.350 (2) | C31—C32 | 1.396 (3) |
C12—C13 | 1.358 (2) | C31—C36 | 1.405 (3) |
C13—O6 | 1.370 (2) | C32—C33 | 1.392 (3) |
C13—C31 | 1.474 (2) | C32—H32 | 0.9500 |
C21—O6 | 1.361 (2) | C33—C34 | 1.382 (3) |
C21—C26 | 1.385 (3) | C33—H33 | 0.9500 |
C21—C22 | 1.394 (3) | C34—C35 | 1.387 (3) |
C22—C23 | 1.378 (3) | C34—H34 | 0.9500 |
C22—H22 | 0.9500 | C35—C36 | 1.390 (3) |
C23—C24 | 1.398 (3) | C35—H35 | 0.9500 |
C23—H23 | 0.9500 | C36—H36 | 0.9500 |
C24—C25 | 1.376 (3) | O5—H5 | 0.8400 |
| | | |
O4—C11—C26 | 124.77 (16) | C21—C26—C25 | 118.36 (17) |
O4—C11—C12 | 119.48 (17) | C21—C26—C11 | 118.94 (16) |
C26—C11—C12 | 115.75 (15) | C25—C26—C11 | 122.69 (16) |
O5—C12—C13 | 121.70 (16) | C32—C31—C36 | 118.82 (17) |
O5—C12—C11 | 116.44 (16) | C32—C31—C13 | 122.02 (16) |
C13—C12—C11 | 121.85 (17) | C36—C31—C13 | 119.12 (17) |
C12—C13—O6 | 120.17 (16) | C33—C32—C31 | 120.28 (18) |
C12—C13—C31 | 128.57 (16) | C33—C32—H32 | 119.9 |
O6—C13—C31 | 111.24 (14) | C31—C32—H32 | 119.9 |
O6—C21—C26 | 122.21 (16) | C34—C33—C32 | 120.43 (19) |
O6—C21—C22 | 115.91 (16) | C34—C33—H33 | 119.8 |
C26—C21—C22 | 121.87 (17) | C32—C33—H33 | 119.8 |
C23—C22—C21 | 118.74 (18) | C33—C34—C35 | 119.96 (18) |
C23—C22—H22 | 120.6 | C33—C34—H34 | 120.0 |
C21—C22—H22 | 120.6 | C35—C34—H34 | 120.0 |
C22—C23—C24 | 120.64 (18) | C34—C35—C36 | 120.16 (18) |
C22—C23—H23 | 119.7 | C34—C35—H35 | 119.9 |
C24—C23—H23 | 119.7 | C36—C35—H35 | 119.9 |
C25—C24—C23 | 120.16 (18) | C35—C36—C31 | 120.32 (18) |
C25—C24—H24 | 119.9 | C35—C36—H36 | 119.8 |
C23—C24—H24 | 119.9 | C31—C36—H36 | 119.8 |
C24—C25—C26 | 120.21 (18) | C12—O5—H5 | 109.5 |
C24—C25—H25 | 119.9 | C21—O6—C13 | 121.00 (14) |
C26—C25—H25 | 119.9 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5···O4 | 0.84 | 2.24 | 2.6680 (19) | 112 |
O5—H5···O4i | 0.84 | 1.93 | 2.7022 (18) | 153 |
C36—H36···O6 | 0.95 | 2.30 | 2.656 (2) | 101 |
C32—H32···O5 | 0.95 | 2.19 | 2.852 (2) | 126 |
Symmetry code: (i) x−1/2, −y+3/2, −z+1. |
Selected bond lengths (Å) and angles (°) for the structures of 1,
3 and 4 top1 | | 3 | | 4 | |
Re1—C1 | 1.905 (3) | Re1—C1 | 1.900 (4) | C11—O4 | 1.238 (2) |
Re1—C2 | 1.892 (3) | Re1—C2 | 1.899 (4) | C12—O5 | 1.350 (2) |
Re1—C3 | 1.889 (3) | Re1—C3 | 1.892 (4) | C13—C31 | 1.474 (2) |
Re1—Br1 | 2.6690 (5) | Re1—O7 | 2.187 (3) | C13—O6 | 1.370 (2) |
Re1—O11 | 2.1292 (19) | Re1—O4 | 2.128 (2) | C21—O6 | 1.361 (2) |
Re1—O12 | 2.1204 (19) | Re1—O5 | 2.149 (2) | | |
| | | | | |
O11—Re1—O12 | 76.78 (7) | O4—Re1—O5 | 76.72 (9) | O4—C11—C12 | 119.48 (17) |
C3—Re1—Br1 | 177.92 (9) | C3—Re1—O7 | 174.51 (13) | O5—C12—C11 | 116.44 (16) |
C3—Re1—O11 | 94.10 (10) | C3—Re1—O5 | 98.98 (12) | C12—O5—H5 | 109.5 |
Summary of the hydrogen-bond interactions and π-interactions observed in
1, 3 and 4 (Å, °) topFor 1, Cg1 is the centroid of atoms Re1, O11, C11, N1 and O12;
Cg2 is the centroid of atoms C12–C17.
For 3, Cg1 is the centroid of atoms Re2, O4, C11, C12 and O5;
Cg2 is the centroid of atoms O6/C11–C13/C21/C26;
Cg4 is the centroid of atoms C31–C36.
For 4, Cg2 is the centroid of atoms C21–C26. |
1 | | | | |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···Br1a | 0.91 (4) | 2.52 (4) | 3.420 (2) | 170 (3) |
C17—H17···O12a | 0.95 | 2.59 | 3.385 (3) | 142.1 |
C23—H23A···O12a | 0.99 | 2.41 | 3.388 (3) | 170.1 |
C25—H25A···O2b | 0.99 | 2.59 | 3.111 (3) | 112.5 |
C25—H25B···O1c | 0.99 | 2.57 | 3.520 (4) | 161.5 |
C26—H26A···O2d | 0.98 | 2.56 | 3.520 (4) | 166.1 |
C27—H27B···O3e | 0.99 | 2.40 | 3.286 (3) | 148.5 |
| | | | |
Y—X(I) | Res(I)→Cg(J) | X···Cg | Y—X···Cg | Y···Cg |
C22—H22Ca | [1] → Cg2 | 2.7074 (4) | 137.86 (25) | 3.496 (5) |
Re1—Br1 | [1] → Cg1 | 2.9666 (12) | 36.575 (8) | 1.7908 (10) |
| | | | |
3 | | | | |
D—H···A | D—H | H···A | D···A | D—H···A |
O7—H7A···O04f | 0.65 (5) | 2.01 (5) | 2.641 (4) | 167 (6) |
O7—H7B···O5g | 0.88 (6) | 1.81 (6) | 2.658 (4) | 162 (6) |
C35—H35···O05h | 0.95 | 2.46 | 3.334 (4) | 153 |
O05—H05···O04 | 0.84 | 2.12 | 2.595 (3) | 115 |
C036—H036···O06 | 0.95 | 2.35 | 2.696 (4) | 101 |
C032—H032···O05 | 0.95 | 2.21 | 2.859 (4) | 125 |
C32—H32···O5 | 0.95 | 2.41 | 2.985 (4) | 119 |
| | | | |
Y—X(I) | Res(I)→Cg(J) | X···Cg | Y—X···Cg | Y···Cg |
O7—H7A | [1] → Cg1 | 2.67 (5) | 57 (4) | 2.379 (4) |
C1—O1i | [1] → Cg2 | 3.500 (3) | 110.7 (3) | 4.057 (4) |
C2—O2i | [1] → Cg4 | 3.377 (4) | 92.5 (2) | 3.617 (5) |
| | | | |
4 | | | | |
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5···O4 | 0.82 | 2.25 | 2.668 (3) | 112 |
O4—H5···O4j | 0.82 | 1.94 | 2.703 (3) | 154 |
C36—H36···O6 | 0.93 | 2.31 | 2.657 (3) | 102 |
C32—H32···O5 | 0.93 | 2.20 | 2.853 (4) | 127 |
| | | | |
Y—X(I) | Res(I)→Cg(J) | X···Cg | Y—X···Cg | Y···Cg |
C23—H23k | [1] → Cg2 | 2.9430 (8) | 140 | 3.702 (4) |
Symmetry code, transformations used to generate equivalent atoms:
(a) -x, -y, -z+1;
(b) x+1, y+1, z+1;
(c) -x+1, -y+1, -z+1;
(d) -x+1, -y, -z+1;
(e) x+1, y, z+1;
(f) -x+1, -y, -z+1;
(g) x, y, z-1;
(h) x+1, y+1, z;
(i) -x+1, -y, -z+1;
(j) x-1/2, -y+3/2, -z+1;
(k) x-1/2, -y+5/2, -z+1. |
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