Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619002717/fn3295sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229619002717/fn329510RMSc3sup2.hkl |
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).
(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 |
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 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 |
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. |
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)* |
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) |
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) |
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. |
[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 |
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 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 |
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. |
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)* |
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) |
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) |
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. |
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 |
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 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) |
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 |
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) |
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) |
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 |
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. |
1 | 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 |
For 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. |