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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-κ2O,O′)bromido­tri­carbonyl­rhenate(I), (C8H20N)[ReBr(C7H6NO2)(CO)3], 1, and fac-aqua­tricarbon­yl(4-oxo-2-phenyl­chromen-3-olato-κ2O,O′)rhenium(I)–3-hy­droxy­flavone (1/1), [Re(C15H9O3)(CO)3(H2O)]·C15H10O3, 3, are reported. Furthermore, the crystal structure of free 3-hy­droxy­flavone, C15H10O3, 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\overline{1} with one mol­ecule in the asymmetric unit, while 4 crystallizes in the ortho­rhom­bic space group P212121. 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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619002717/fn3295sup1.cif
Contains datablocks 7LMaSc1, 10Amsc4, 10RMSc3, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619002717/fn329510RMSc3sup2.hkl
Contains datablock 10RMSc3

CCDC references: 1580730; 1580732; 1580731

Computing details top

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 = 616.52F(000) = 596
Triclinic, P1Dx = 1.987 Mg m3
a = 9.6321 (13) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.8793 (11) ÅCell parameters from 5976 reflections
c = 12.826 (2) Åθ = 2.5–28.3°
α = 95.806 (10)°µ = 7.87 mm1
β = 108.520 (11)°T = 100 K
γ = 112.895 (7)°Cuboid, colourless
V = 1030.2 (3) Å30.38 × 0.25 × 0.11 mm
Data collection top
CCD area detector
diffractometer
4720 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.038
phi and ω scansθmax = 28.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 1212
Tmin = 0.109, Tmax = 0.421k = 1313
18080 measured reflectionsl = 1616
4957 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.021H 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 reflectionsΔρmax = 1.78 e Å3
252 parametersΔρmin = 1.91 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.1854 (4)0.1312 (3)0.1675 (2)0.0131 (5)
C20.0337 (3)0.1441 (3)0.1472 (2)0.0134 (5)
C30.1219 (4)0.0805 (3)0.1303 (2)0.0143 (6)
C110.0637 (3)0.2422 (3)0.4379 (2)0.0090 (5)
C120.1205 (3)0.3743 (3)0.5326 (2)0.0089 (5)
C130.1932 (3)0.5189 (3)0.5164 (2)0.0112 (5)
H130.2005840.5292940.4452780.013*
C140.2547 (4)0.6473 (3)0.6036 (2)0.0155 (6)
H140.3042640.7455320.5923240.019*
C150.2437 (3)0.6319 (3)0.7075 (2)0.0158 (6)
H150.2856820.7196610.7675270.019*
C160.1712 (3)0.4878 (3)0.7236 (2)0.0141 (5)
H160.1635080.4776990.7946850.017*
C170.1099 (3)0.3586 (3)0.6367 (2)0.0108 (5)
H170.0610470.2604130.6482350.013*
C210.5420 (4)0.3084 (3)0.6767 (2)0.0159 (6)
H21A0.6218770.2926730.6501990.019*
H21B0.4350370.2179750.6362140.019*
C220.5261 (4)0.4462 (4)0.6438 (3)0.0216 (7)
H22A0.4690270.4220690.5610920.032*
H22B0.6352060.5311770.6676250.032*
H22C0.4636080.4746170.6813410.032*
C230.4561 (3)0.3052 (3)0.8386 (2)0.0132 (5)
H23A0.3570210.2120110.7881580.016*
H23B0.4333280.3930350.8261190.016*
C240.4852 (4)0.2995 (4)0.9611 (2)0.0211 (6)
H24A0.3892190.2916830.9762470.032*
H24B0.5814100.3923651.0122140.032*
H24C0.5039360.2108580.9740560.032*
C250.7425 (3)0.4676 (3)0.8731 (2)0.0122 (5)
H25A0.7753530.4660130.9541540.015*
H25B0.7090860.5502020.8650050.015*
C260.8911 (3)0.5058 (3)0.8422 (2)0.0165 (6)
H26A0.9257420.4249850.8495870.025*
H26B0.9806490.6024660.8935610.025*
H26C0.8626430.5146040.7635580.025*
C270.6407 (3)0.1891 (3)0.8242 (2)0.0143 (6)
H27A0.7250490.1961240.7938070.017*
H27B0.6898990.2027420.9073680.017*
C280.4989 (4)0.0316 (3)0.7716 (3)0.0222 (7)
H28A0.5384130.0446340.7879620.033*
H28B0.4497900.0159950.6890260.033*
H28C0.4166090.0213970.8036240.033*
N10.0464 (3)0.1077 (2)0.43186 (18)0.0093 (4)
N20.5959 (3)0.3183 (2)0.80319 (17)0.0087 (4)
O10.2774 (3)0.1839 (2)0.12566 (18)0.0208 (5)
O20.0760 (3)0.2637 (2)0.09062 (17)0.0204 (5)
O30.2210 (3)0.0988 (2)0.06245 (18)0.0223 (5)
O110.1223 (2)0.2589 (2)0.36066 (15)0.0122 (4)
O120.0965 (2)0.0148 (2)0.34430 (15)0.0105 (4)
Br10.26528 (3)0.01265 (3)0.40365 (2)0.01252 (6)
Re10.03945 (2)0.05041 (2)0.24114 (2)0.00857 (4)
H10.093 (4)0.086 (4)0.483 (3)0.026 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0205 (15)0.0112 (12)0.0077 (11)0.0075 (11)0.0051 (11)0.0023 (10)
C20.0164 (14)0.0194 (14)0.0095 (12)0.0106 (11)0.0070 (11)0.0067 (11)
C30.0189 (15)0.0098 (12)0.0110 (12)0.0029 (11)0.0069 (11)0.0012 (10)
C110.0095 (12)0.0113 (12)0.0074 (11)0.0054 (10)0.0036 (10)0.0035 (9)
C120.0081 (12)0.0095 (12)0.0089 (11)0.0039 (9)0.0038 (10)0.0000 (9)
C130.0102 (13)0.0130 (12)0.0115 (12)0.0054 (10)0.0052 (10)0.0037 (10)
C140.0161 (14)0.0113 (13)0.0165 (13)0.0044 (11)0.0057 (11)0.0018 (10)
C150.0152 (14)0.0138 (13)0.0145 (13)0.0050 (11)0.0048 (11)0.0024 (10)
C160.0125 (13)0.0187 (14)0.0109 (12)0.0056 (11)0.0066 (11)0.0017 (10)
C170.0079 (12)0.0131 (12)0.0114 (12)0.0040 (10)0.0051 (10)0.0021 (10)
C210.0162 (14)0.0218 (14)0.0055 (11)0.0048 (11)0.0040 (10)0.0021 (10)
C220.0168 (15)0.0314 (17)0.0206 (15)0.0112 (13)0.0082 (12)0.0174 (13)
C230.0087 (13)0.0168 (13)0.0148 (13)0.0048 (10)0.0068 (10)0.0030 (10)
C240.0230 (16)0.0267 (16)0.0177 (14)0.0091 (13)0.0151 (13)0.0074 (12)
C250.0100 (13)0.0108 (12)0.0094 (12)0.0007 (10)0.0019 (10)0.0010 (10)
C260.0107 (13)0.0168 (14)0.0190 (14)0.0024 (11)0.0067 (11)0.0052 (11)
C270.0136 (14)0.0111 (12)0.0172 (13)0.0057 (10)0.0045 (11)0.0041 (10)
C280.0180 (15)0.0095 (13)0.0385 (18)0.0037 (11)0.0142 (14)0.0039 (12)
N10.0109 (11)0.0095 (10)0.0067 (10)0.0036 (8)0.0044 (9)0.0002 (8)
N20.0081 (11)0.0100 (10)0.0072 (10)0.0034 (8)0.0032 (8)0.0015 (8)
O10.0271 (12)0.0249 (11)0.0216 (11)0.0143 (9)0.0180 (10)0.0122 (9)
O20.0265 (12)0.0133 (10)0.0167 (10)0.0092 (9)0.0039 (9)0.0012 (8)
O30.0241 (12)0.0253 (11)0.0177 (10)0.0133 (9)0.0044 (9)0.0100 (9)
O110.0163 (10)0.0100 (9)0.0098 (9)0.0039 (7)0.0075 (8)0.0011 (7)
O120.0120 (9)0.0067 (8)0.0086 (9)0.0004 (7)0.0049 (7)0.0022 (7)
Br10.01056 (13)0.01808 (13)0.00890 (12)0.00574 (10)0.00462 (10)0.00339 (10)
Re10.01144 (6)0.00867 (6)0.00553 (6)0.00374 (4)0.00431 (4)0.00140 (4)
Geometric parameters (Å, º) top
C1—O11.159 (3)C23—N21.517 (4)
C1—Re11.905 (3)C23—C241.518 (4)
C2—O21.163 (3)C23—H23A0.9900
C2—Re11.892 (3)C23—H23B0.9900
C3—O31.157 (3)C24—H24A0.9800
C3—Re11.889 (3)C24—H24B0.9800
C11—O111.282 (3)C24—H24C0.9800
C11—N11.314 (3)C25—N21.510 (3)
C11—C121.476 (4)C25—C261.523 (4)
C12—C171.391 (3)C25—H25A0.9900
C12—C131.396 (3)C25—H25B0.9900
C13—C141.384 (4)C26—H26A0.9800
C13—H130.9500C26—H26B0.9800
C14—C151.389 (4)C26—H26C0.9800
C14—H140.9500C27—C281.513 (4)
C15—C161.390 (4)C27—N21.521 (3)
C15—H150.9500C27—H27A0.9900
C16—C171.388 (4)C27—H27B0.9900
C16—H160.9500C28—H28A0.9800
C17—H170.9500C28—H28B0.9800
C21—C221.515 (4)C28—H28C0.9800
C21—N21.518 (3)N1—O121.373 (3)
C21—H21A0.9900N1—H10.91 (4)
C21—H21B0.9900O11—Re12.1292 (19)
C22—H22A0.9800O12—Re12.1204 (19)
C22—H22B0.9800Br1—Re12.6690 (5)
C22—H22C0.9800
O1—C1—Re1177.9 (2)N2—C25—H25A108.4
O2—C2—Re1178.7 (3)C26—C25—H25A108.4
O3—C3—Re1179.9 (3)N2—C25—H25B108.4
O11—C11—N1119.6 (2)C26—C25—H25B108.4
O11—C11—C12119.6 (2)H25A—C25—H25B107.5
N1—C11—C12120.8 (2)C25—C26—H26A109.5
C17—C12—C13120.0 (2)C25—C26—H26B109.5
C17—C12—C11122.3 (2)H26A—C26—H26B109.5
C13—C12—C11117.6 (2)C25—C26—H26C109.5
C14—C13—C12120.3 (2)H26A—C26—H26C109.5
C14—C13—H13119.8H26B—C26—H26C109.5
C12—C13—H13119.8C28—C27—N2114.7 (2)
C13—C14—C15119.8 (2)C28—C27—H27A108.6
C13—C14—H14120.1N2—C27—H27A108.6
C15—C14—H14120.1C28—C27—H27B108.6
C14—C15—C16119.9 (3)N2—C27—H27B108.6
C14—C15—H15120.0H27A—C27—H27B107.6
C16—C15—H15120.0C27—C28—H28A109.5
C17—C16—C15120.6 (3)C27—C28—H28B109.5
C17—C16—H16119.7H28A—C28—H28B109.5
C15—C16—H16119.7C27—C28—H28C109.5
C16—C17—C12119.4 (2)H28A—C28—H28C109.5
C16—C17—H17120.3H28B—C28—H28C109.5
C12—C17—H17120.3C11—N1—O12120.2 (2)
C22—C21—N2115.0 (2)C11—N1—H1125 (2)
C22—C21—H21A108.5O12—N1—H1114 (2)
N2—C21—H21A108.5C25—N2—C23108.3 (2)
C22—C21—H21B108.5C25—N2—C21111.85 (19)
N2—C21—H21B108.5C23—N2—C21108.7 (2)
H21A—C21—H21B107.5C25—N2—C27109.0 (2)
C21—C22—H22A109.5C23—N2—C27111.0 (2)
C21—C22—H22B109.5C21—N2—C27108.1 (2)
H22A—C22—H22B109.5C11—O11—Re1113.20 (16)
C21—C22—H22C109.5N1—O12—Re1109.83 (14)
H22A—C22—H22C109.5C3—Re1—C289.93 (12)
H22B—C22—H22C109.5C3—Re1—C189.58 (12)
N2—C23—C24115.2 (2)C2—Re1—C188.02 (12)
N2—C23—H23A108.5C3—Re1—O1294.96 (10)
C24—C23—H23A108.5C2—Re1—O1298.84 (10)
N2—C23—H23B108.5C1—Re1—O12171.76 (9)
C24—C23—H23B108.5C3—Re1—O1194.10 (10)
H23A—C23—H23B107.5C2—Re1—O11174.27 (8)
C23—C24—H24A109.5C1—Re1—O1196.07 (9)
C23—C24—H24B109.5O12—Re1—O1176.78 (7)
H24A—C24—H24B109.5C3—Re1—Br1177.92 (9)
C23—C24—H24C109.5C2—Re1—Br191.65 (8)
H24A—C24—H24C109.5C1—Re1—Br191.82 (8)
H24B—C24—H24C109.5O12—Re1—Br183.47 (5)
N2—C25—C26115.5 (2)O11—Re1—Br184.23 (5)
O11—C11—C12—C17156.9 (3)C26—C25—N2—C2155.6 (3)
N1—C11—C12—C1723.2 (4)C26—C25—N2—C2763.9 (3)
O11—C11—C12—C1320.4 (4)C24—C23—N2—C2563.3 (3)
N1—C11—C12—C13159.5 (2)C24—C23—N2—C21175.0 (2)
C17—C12—C13—C140.1 (4)C24—C23—N2—C2756.3 (3)
C11—C12—C13—C14177.5 (3)C22—C21—N2—C2548.1 (3)
C12—C13—C14—C150.1 (4)C22—C21—N2—C2371.4 (3)
C13—C14—C15—C160.0 (4)C22—C21—N2—C27168.1 (2)
C14—C15—C16—C170.2 (4)C28—C27—N2—C25172.4 (2)
C15—C16—C17—C120.4 (4)C28—C27—N2—C2353.3 (3)
C13—C12—C17—C160.4 (4)C28—C27—N2—C2165.8 (3)
C11—C12—C17—C16177.6 (3)N1—C11—O11—Re15.3 (3)
O11—C11—N1—O121.1 (4)C12—C11—O11—Re1174.80 (18)
C12—C11—N1—O12179.0 (2)C11—N1—O12—Re13.7 (3)
C26—C25—N2—C23175.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···Br1i0.91 (4)2.52 (4)3.420 (2)170 (3)
C23—H23A···O12i0.992.413.388 (3)170
C25—H25B···O1ii0.992.573.520 (4)162
C26—H26A···O2iii0.982.563.520 (4)166
C27—H27B···O3iv0.992.403.286 (3)149
C17—H17···O12i0.952.593.385 (3)142
C25—H25A···O2v0.992.593.111 (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)]·C15H10O3Z = 2
Mr = 763.70F(000) = 748
Triclinic, P1Dx = 1.864 Mg m3
a = 10.5209 (15) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.9365 (17) ÅCell parameters from 9860 reflections
c = 12.4455 (17) Åθ = 2.9–28.6°
α = 108.277 (7)°µ = 4.53 mm1
β = 102.745 (7)°T = 100 K
γ = 104.252 (7)°Cuboid, yellow
V = 1361.0 (3) Å30.55 × 0.17 × 0.08 mm
Data collection top
Bruker APEXII CCD
diffractometer
6045 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.038
φ and ω scansθmax = 28.6°, θmin = 3.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 1414
Tmin = 0.417, Tmax = 0.699k = 1616
23222 measured reflectionsl = 1616
6700 independent reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.027H 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 reflectionsΔρmax = 1.40 e Å3
406 parametersΔρmin = 2.10 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.5140 (4)0.2364 (3)0.4055 (3)0.0199 (7)
C20.3810 (4)0.2744 (3)0.1859 (3)0.0204 (7)
C30.6494 (4)0.2215 (3)0.2549 (3)0.0196 (7)
C110.6247 (4)0.0961 (3)0.2846 (3)0.0198 (7)
C0110.2049 (3)0.0071 (3)1.1005 (3)0.0202 (7)
C0120.1389 (3)0.0859 (3)0.9754 (3)0.0192 (7)
C120.6965 (4)0.1271 (3)0.4072 (3)0.0190 (7)
C0130.1113 (3)0.0380 (3)0.8907 (3)0.0175 (7)
C130.7720 (4)0.2509 (3)0.4809 (3)0.0189 (7)
C210.7148 (4)0.3169 (3)0.3205 (3)0.0209 (7)
C0210.2151 (3)0.1691 (3)1.0409 (3)0.0189 (7)
C220.7313 (4)0.4166 (3)0.2842 (3)0.0239 (8)
H220.7871060.4992690.3394700.029*
C0220.2528 (4)0.2964 (3)1.0638 (3)0.0229 (7)
H0220.2323800.3245541.0006920.027*
C230.6658 (4)0.3942 (4)0.1671 (3)0.0255 (8)
H230.6763810.4619210.1413260.031*
C0230.3209 (4)0.3812 (4)1.1806 (3)0.0252 (8)
H0230.3475740.4686511.1980320.030*
C240.5831 (4)0.2715 (4)0.0852 (3)0.0227 (7)
H240.5372250.2564930.0045520.027*
C0240.3510 (4)0.3394 (4)1.2738 (3)0.0261 (8)
H0240.3978560.3987811.3536070.031*
C0250.3136 (4)0.2146 (4)1.2504 (3)0.0230 (8)
H0250.3338510.1869761.3139090.028*
C250.5693 (4)0.1744 (3)0.1224 (3)0.0195 (7)
H250.5134230.0916960.0671870.023*
C0260.2446 (3)0.1261 (3)1.1318 (3)0.0187 (7)
C260.6363 (4)0.1949 (3)0.2411 (3)0.0194 (7)
C310.8486 (3)0.3033 (3)0.6094 (3)0.0186 (7)
C0310.0386 (3)0.1072 (3)0.7614 (3)0.0184 (7)
C320.9040 (4)0.2321 (3)0.6644 (3)0.0211 (7)
H320.8875870.1462750.6194420.025*
C0320.0070 (4)0.2361 (3)0.7066 (3)0.0225 (7)
H0320.0361210.2812270.7521950.027*
C0330.0667 (4)0.2990 (4)0.5857 (3)0.0267 (8)
H0330.0868900.3869340.5490630.032*
C330.9827 (4)0.2869 (3)0.7842 (3)0.0220 (7)
H331.0205530.2381590.8205730.026*
C0340.1115 (4)0.2356 (4)0.5174 (3)0.0242 (8)
H0340.1640750.2798740.4350070.029*
C341.0072 (4)0.4102 (4)0.8516 (3)0.0231 (7)
H341.0632530.4470200.9332910.028*
C350.9494 (4)0.4802 (3)0.7994 (3)0.0238 (8)
H350.9632140.5648890.8462170.029*
C0350.0788 (4)0.1076 (4)0.5705 (3)0.0272 (8)
H0350.1081300.0631430.5242320.033*
C360.8714 (4)0.4280 (3)0.6793 (3)0.0211 (7)
H360.8331460.4774050.6442070.025*
C0360.0031 (4)0.0433 (3)0.6912 (3)0.0249 (8)
H0360.0205030.0452210.7264280.030*
O10.5028 (3)0.2981 (3)0.4610 (2)0.0277 (6)
O20.2923 (3)0.3565 (3)0.1074 (2)0.0297 (6)
O30.7187 (3)0.2755 (3)0.2184 (2)0.0305 (6)
O040.2208 (3)0.0595 (2)1.1723 (2)0.0242 (5)
O40.5511 (3)0.0166 (2)0.2184 (2)0.0210 (5)
O50.6847 (2)0.0325 (2)0.4444 (2)0.0191 (5)
O050.1030 (3)0.2108 (2)0.9494 (2)0.0250 (6)
H050.1327310.2226941.0117720.038*
O60.7796 (2)0.3434 (2)0.4386 (2)0.0200 (5)
O060.1490 (2)0.0888 (2)0.9236 (2)0.0191 (5)
O70.4034 (3)0.0289 (2)0.3719 (3)0.0209 (6)
Re10.53064 (2)0.13900 (2)0.31117 (2)0.01536 (4)
H7A0.354 (5)0.031 (4)0.329 (4)0.021 (13)*
H7B0.369 (5)0.047 (5)0.425 (5)0.045 (15)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0201 (17)0.0165 (17)0.0177 (16)0.0051 (14)0.0020 (14)0.0035 (14)
C20.0226 (17)0.0241 (19)0.0163 (16)0.0082 (15)0.0088 (14)0.0082 (15)
C30.0207 (17)0.0171 (17)0.0152 (16)0.0029 (14)0.0020 (13)0.0042 (13)
C110.0214 (17)0.0195 (18)0.0183 (16)0.0087 (14)0.0062 (14)0.0059 (14)
C0110.0151 (15)0.0267 (19)0.0200 (17)0.0096 (14)0.0048 (13)0.0093 (15)
C0120.0150 (15)0.0181 (17)0.0227 (17)0.0053 (13)0.0035 (13)0.0079 (14)
C120.0196 (16)0.0160 (17)0.0209 (17)0.0071 (14)0.0071 (14)0.0052 (14)
C0130.0144 (15)0.0161 (16)0.0205 (16)0.0058 (13)0.0037 (13)0.0061 (14)
C130.0195 (16)0.0185 (17)0.0190 (16)0.0065 (14)0.0056 (14)0.0083 (14)
C210.0230 (17)0.0227 (19)0.0166 (16)0.0097 (15)0.0053 (14)0.0065 (14)
C0210.0153 (15)0.0223 (18)0.0162 (16)0.0079 (14)0.0024 (13)0.0046 (14)
C220.0291 (19)0.0166 (18)0.0224 (18)0.0058 (15)0.0042 (15)0.0073 (15)
C0220.0229 (17)0.0210 (18)0.0214 (17)0.0101 (15)0.0020 (14)0.0056 (15)
C230.0298 (19)0.024 (2)0.0246 (19)0.0094 (16)0.0070 (16)0.0137 (16)
C0230.0240 (18)0.0202 (19)0.0258 (19)0.0077 (15)0.0037 (15)0.0048 (15)
C240.0245 (18)0.029 (2)0.0170 (17)0.0115 (16)0.0072 (14)0.0105 (15)
C0240.0242 (18)0.026 (2)0.0190 (17)0.0084 (16)0.0004 (15)0.0012 (15)
C0250.0188 (17)0.029 (2)0.0176 (17)0.0073 (15)0.0026 (14)0.0080 (15)
C250.0203 (16)0.0205 (18)0.0170 (16)0.0080 (14)0.0050 (14)0.0061 (14)
C0260.0136 (15)0.0217 (18)0.0192 (16)0.0067 (13)0.0037 (13)0.0066 (14)
C260.0189 (16)0.0214 (18)0.0184 (16)0.0073 (14)0.0063 (14)0.0081 (14)
C310.0165 (16)0.0184 (17)0.0166 (16)0.0040 (13)0.0029 (13)0.0045 (14)
C0310.0163 (15)0.0216 (18)0.0185 (16)0.0083 (14)0.0047 (13)0.0088 (14)
C320.0205 (17)0.0176 (18)0.0196 (17)0.0078 (14)0.0012 (14)0.0027 (14)
C0320.0256 (18)0.0202 (18)0.0219 (18)0.0081 (15)0.0056 (15)0.0095 (15)
C0330.036 (2)0.0195 (19)0.0204 (18)0.0080 (16)0.0051 (16)0.0064 (15)
C330.0193 (17)0.0253 (19)0.0186 (17)0.0075 (15)0.0017 (14)0.0081 (15)
C0340.0283 (19)0.0232 (19)0.0157 (16)0.0066 (15)0.0026 (15)0.0052 (14)
C340.0191 (17)0.028 (2)0.0192 (17)0.0053 (15)0.0049 (14)0.0077 (15)
C350.0284 (19)0.0151 (17)0.0214 (18)0.0009 (15)0.0058 (15)0.0053 (14)
C0350.037 (2)0.026 (2)0.0187 (17)0.0150 (17)0.0029 (16)0.0100 (16)
C360.0264 (18)0.0156 (17)0.0191 (17)0.0072 (14)0.0046 (14)0.0057 (14)
C0360.032 (2)0.0180 (18)0.0221 (18)0.0109 (16)0.0043 (16)0.0064 (15)
O10.0321 (14)0.0296 (15)0.0262 (14)0.0114 (12)0.0075 (12)0.0176 (12)
O20.0269 (14)0.0269 (15)0.0207 (13)0.0043 (12)0.0038 (11)0.0039 (12)
O30.0307 (14)0.0344 (16)0.0299 (15)0.0169 (13)0.0121 (12)0.0107 (13)
O040.0247 (13)0.0261 (14)0.0215 (13)0.0077 (11)0.0019 (11)0.0134 (11)
O40.0252 (13)0.0185 (13)0.0187 (12)0.0080 (10)0.0052 (10)0.0072 (10)
O50.0207 (12)0.0169 (12)0.0150 (11)0.0052 (10)0.0016 (10)0.0041 (10)
O050.0311 (14)0.0188 (13)0.0213 (13)0.0075 (11)0.0003 (11)0.0093 (11)
O60.0238 (12)0.0134 (12)0.0175 (12)0.0034 (10)0.0008 (10)0.0054 (10)
O060.0202 (12)0.0164 (12)0.0169 (11)0.0067 (10)0.0006 (10)0.0049 (10)
O70.0211 (13)0.0229 (14)0.0177 (13)0.0105 (11)0.0016 (12)0.0079 (11)
Re10.01730 (7)0.01368 (7)0.01221 (7)0.00484 (5)0.00184 (5)0.00370 (5)
Geometric parameters (Å, º) top
C1—O11.160 (4)C24—H240.9500
C1—Re11.900 (4)C024—C0251.360 (5)
C2—O21.154 (4)C024—H0240.9500
C2—Re11.899 (4)C025—C0261.412 (5)
C3—O31.161 (4)C025—H0250.9500
C3—Re11.892 (4)C25—C261.403 (5)
C11—O41.265 (4)C25—H250.9500
C11—C121.426 (5)C31—C361.397 (5)
C11—C261.433 (5)C31—C321.400 (5)
C011—O041.246 (4)C031—C0321.390 (5)
C011—C0261.438 (5)C031—C0361.398 (5)
C011—C0121.441 (5)C32—C331.384 (5)
C012—O051.354 (4)C32—H320.9500
C012—C0131.359 (5)C032—C0331.385 (5)
C12—O51.338 (4)C032—H0320.9500
C12—C131.380 (5)C033—C0341.385 (5)
C013—O061.364 (4)C033—H0330.9500
C013—C0311.473 (5)C33—C341.370 (5)
C13—O61.357 (4)C33—H330.9500
C13—C311.468 (5)C034—C0351.377 (5)
C21—O61.373 (4)C034—H0340.9500
C21—C221.385 (5)C34—C351.381 (5)
C21—C261.388 (5)C34—H340.9500
C021—O061.371 (4)C35—C361.385 (5)
C021—C0221.389 (5)C35—H350.9500
C021—C0261.389 (5)C035—C0361.388 (5)
C22—C231.376 (5)C035—H0350.9500
C22—H220.9500C36—H360.9500
C022—C0231.383 (5)C036—H0360.9500
C022—H0220.9500O4—Re12.128 (2)
C23—C241.410 (5)O5—Re12.149 (2)
C23—H230.9500O05—H050.8400
C023—C0241.404 (5)O7—Re12.187 (3)
C023—H0230.9500O7—H7A0.65 (4)
C24—C251.366 (5)O7—H7B0.87 (5)
O1—C1—Re1178.6 (3)C36—C31—C13120.0 (3)
O2—C2—Re1177.9 (3)C32—C31—C13121.6 (3)
O3—C3—Re1177.9 (3)C032—C031—C036118.4 (3)
O4—C11—C12119.3 (3)C032—C031—C013121.8 (3)
O4—C11—C26122.1 (3)C036—C031—C013119.7 (3)
C12—C11—C26118.6 (3)C33—C32—C31119.9 (3)
O04—C011—C026125.6 (3)C33—C32—H32120.1
O04—C011—C012117.7 (3)C31—C32—H32120.1
C026—C011—C012116.7 (3)C033—C032—C031120.2 (3)
O05—C012—C013122.8 (3)C033—C032—H032119.9
O05—C012—C011115.0 (3)C031—C032—H032119.9
C013—C012—C011122.2 (3)C032—C033—C034121.0 (3)
O5—C12—C13123.6 (3)C032—C033—H033119.5
O5—C12—C11117.0 (3)C034—C033—H033119.5
C13—C12—C11119.4 (3)C34—C33—C32121.4 (3)
C012—C013—O06119.6 (3)C34—C33—H33119.3
C012—C013—C031127.9 (3)C32—C33—H33119.3
O06—C013—C031112.5 (3)C035—C034—C033119.1 (3)
O6—C13—C12121.1 (3)C035—C034—H034120.4
O6—C13—C31110.7 (3)C033—C034—H034120.4
C12—C13—C31128.1 (3)C33—C34—C35119.3 (3)
O6—C21—C22117.4 (3)C33—C34—H34120.4
O6—C21—C26121.0 (3)C35—C34—H34120.4
C22—C21—C26121.6 (3)C34—C35—C36120.5 (3)
O06—C021—C022116.3 (3)C34—C35—H35119.8
O06—C021—C026122.1 (3)C36—C35—H35119.8
C022—C021—C026121.6 (3)C034—C035—C036120.4 (3)
C23—C22—C21119.1 (3)C034—C035—H035119.8
C23—C22—H22120.4C036—C035—H035119.8
C21—C22—H22120.4C35—C36—C31120.6 (3)
C023—C022—C021118.4 (3)C35—C36—H36119.7
C023—C022—H022120.8C31—C36—H36119.7
C021—C022—H022120.8C035—C036—C031120.8 (3)
C22—C23—C24120.4 (3)C035—C036—H036119.6
C22—C23—H23119.8C031—C036—H036119.6
C24—C23—H23119.8C11—O4—Re1114.1 (2)
C022—C023—C024120.7 (4)C12—O5—Re1111.7 (2)
C022—C023—H023119.6C012—O05—H05109.5
C024—C023—H023119.6C13—O6—C21121.2 (3)
C25—C24—C23119.6 (3)C013—O06—C021121.1 (3)
C25—C24—H24120.2Re1—O7—H7A114 (4)
C23—C24—H24120.2Re1—O7—H7B114 (3)
C025—C024—C023120.4 (3)H7A—O7—H7B110 (5)
C025—C024—H024119.8C3—Re1—C287.10 (15)
C023—C024—H024119.8C3—Re1—C187.17 (15)
C024—C025—C026120.0 (3)C2—Re1—C187.16 (15)
C024—C025—H025120.0C3—Re1—O496.33 (13)
C026—C025—H025120.0C2—Re1—O496.34 (12)
C24—C25—C26121.0 (3)C1—Re1—O4175.16 (12)
C24—C25—H25119.5C3—Re1—O598.98 (12)
C26—C25—H25119.5C2—Re1—O5171.17 (12)
C021—C026—C025118.8 (3)C1—Re1—O599.46 (12)
C021—C026—C011118.3 (3)O4—Re1—O576.72 (9)
C025—C026—C011122.9 (3)C3—Re1—O7174.51 (13)
C21—C26—C25118.3 (3)C2—Re1—O795.38 (13)
C21—C26—C11118.7 (3)C1—Re1—O797.83 (13)
C25—C26—C11123.0 (3)O4—Re1—O778.55 (10)
C36—C31—C32118.4 (3)O5—Re1—O778.02 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O7—H7A···O04i0.65 (4)2.00 (5)2.641 (4)167 (5)
O7—H7B···O5ii0.87 (5)1.81 (6)2.658 (4)162 (5)
O05—H05···O040.842.122.595 (4)115
C036—H036···O060.952.352.696 (4)101
C032—H032···O050.952.212.859 (4)125
C32—H32···O50.952.412.985 (4)119
C35—H35···O05iii0.952.463.334 (4)153
Symmetry codes: (i) x, y, z1; (ii) x+1, y, z+1; (iii) x+1, y+1, z.
2-Phenylchromen-4-one (10RMSc3) top
Crystal data top
C15H10O3Dx = 1.442 Mg m3
Mr = 238.23Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 6732 reflections
a = 5.3502 (6) Åθ = 2.9–28.2°
b = 11.3531 (14) ŵ = 0.10 mm1
c = 18.063 (2) ÅT = 100 K
V = 1097.2 (2) Å3Cuboid, colourless
Z = 40.37 × 0.17 × 0.15 mm
F(000) = 496
Data collection top
Bruker APEXII CCD
diffractometer
2376 reflections with I > 2σ(I)
Radiation source: sealed tubeRint = 0.033
φ and ω scansθmax = 28.0°, θmin = 3.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 77
Tmin = 0.980, Tmax = 0.985k = 1414
17120 measured reflectionsl = 2323
2621 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-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 = 1.07Δρmax = 0.21 e Å3
2621 reflectionsΔρmin = 0.21 e Å3
165 parametersAbsolute structure: Refined as an inversion twin
0 restraintsAbsolute 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
xyzUiso*/Ueq
C110.1494 (3)0.89389 (16)0.55141 (10)0.0162 (4)
C120.0276 (3)0.89383 (16)0.61248 (10)0.0163 (4)
C130.0335 (3)0.98193 (15)0.66332 (10)0.0164 (4)
C210.3073 (3)1.07756 (16)0.60398 (10)0.0174 (4)
C220.4691 (4)1.17374 (17)0.60567 (11)0.0203 (4)
H220.4528711.2325500.6427780.024*
C230.6529 (4)1.18193 (17)0.55248 (11)0.0222 (4)
H230.7639641.2472330.5527630.027*
C240.6776 (4)1.09508 (17)0.49812 (11)0.0215 (4)
H240.8056451.1014080.4618860.026*
C250.5170 (3)1.00045 (17)0.49696 (10)0.0189 (4)
H250.5349730.9414150.4600640.023*
C260.3258 (3)0.99081 (16)0.55035 (10)0.0172 (4)
C310.2061 (3)0.99745 (17)0.72618 (10)0.0176 (4)
C320.4076 (4)0.92170 (17)0.73825 (10)0.0192 (4)
H320.4308580.8552440.7070500.023*
C330.5745 (4)0.94314 (18)0.79582 (11)0.0215 (4)
H330.7120230.8916250.8033820.026*
C340.5413 (4)1.03891 (18)0.84203 (11)0.0225 (4)
H340.6570241.0535990.8808460.027*
C350.3390 (4)1.11355 (18)0.83171 (11)0.0237 (4)
H350.3144631.1784380.8641160.028*
C360.1722 (4)1.09365 (17)0.77409 (10)0.0203 (4)
H360.0346001.1453320.7670480.024*
O40.1397 (2)0.81458 (11)0.50448 (7)0.0202 (3)
O50.1881 (3)0.80217 (12)0.61550 (7)0.0204 (3)
H50.1930230.7686170.5740780.031*
O60.1319 (2)1.07378 (11)0.65851 (7)0.0182 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C110.0176 (9)0.0150 (9)0.0159 (9)0.0034 (7)0.0022 (7)0.0001 (7)
C120.0180 (9)0.0148 (9)0.0161 (9)0.0008 (7)0.0027 (7)0.0017 (7)
C130.0183 (8)0.0137 (9)0.0170 (9)0.0003 (7)0.0019 (7)0.0015 (7)
C210.0184 (9)0.0161 (9)0.0176 (9)0.0014 (7)0.0014 (7)0.0033 (8)
C220.0223 (10)0.0151 (9)0.0234 (10)0.0005 (7)0.0035 (8)0.0004 (8)
C230.0208 (9)0.0183 (9)0.0274 (10)0.0022 (8)0.0020 (8)0.0050 (8)
C240.0181 (9)0.0237 (10)0.0227 (10)0.0013 (8)0.0008 (8)0.0044 (8)
C250.0195 (9)0.0183 (9)0.0189 (9)0.0037 (8)0.0000 (7)0.0009 (8)
C260.0184 (9)0.0157 (9)0.0175 (9)0.0024 (7)0.0023 (7)0.0021 (7)
C310.0199 (8)0.0165 (9)0.0163 (9)0.0046 (7)0.0018 (7)0.0013 (7)
C320.0220 (9)0.0167 (9)0.0188 (9)0.0017 (7)0.0023 (7)0.0009 (8)
C330.0221 (10)0.0209 (10)0.0217 (10)0.0032 (8)0.0005 (7)0.0033 (8)
C340.0248 (9)0.0245 (10)0.0184 (9)0.0088 (8)0.0024 (7)0.0009 (8)
C350.0280 (10)0.0232 (10)0.0198 (10)0.0063 (8)0.0022 (8)0.0045 (8)
C360.0226 (9)0.0184 (10)0.0198 (10)0.0005 (7)0.0026 (7)0.0007 (7)
O40.0233 (7)0.0181 (7)0.0190 (7)0.0000 (5)0.0006 (5)0.0044 (5)
O50.0245 (7)0.0181 (7)0.0187 (7)0.0053 (6)0.0025 (5)0.0046 (5)
O60.0218 (6)0.0146 (6)0.0184 (7)0.0027 (5)0.0010 (5)0.0028 (5)
Geometric parameters (Å, º) top
C11—O41.238 (2)C24—H240.9500
C11—C261.450 (3)C25—C261.410 (3)
C11—C121.454 (2)C25—H250.9500
C12—O51.350 (2)C31—C321.396 (3)
C12—C131.358 (2)C31—C361.405 (3)
C13—O61.370 (2)C32—C331.392 (3)
C13—C311.474 (2)C32—H320.9500
C21—O61.361 (2)C33—C341.382 (3)
C21—C261.385 (3)C33—H330.9500
C21—C221.394 (3)C34—C351.387 (3)
C22—C231.378 (3)C34—H340.9500
C22—H220.9500C35—C361.390 (3)
C23—C241.398 (3)C35—H350.9500
C23—H230.9500C36—H360.9500
C24—C251.376 (3)O5—H50.8400
O4—C11—C26124.77 (16)C21—C26—C25118.36 (17)
O4—C11—C12119.48 (17)C21—C26—C11118.94 (16)
C26—C11—C12115.75 (15)C25—C26—C11122.69 (16)
O5—C12—C13121.70 (16)C32—C31—C36118.82 (17)
O5—C12—C11116.44 (16)C32—C31—C13122.02 (16)
C13—C12—C11121.85 (17)C36—C31—C13119.12 (17)
C12—C13—O6120.17 (16)C33—C32—C31120.28 (18)
C12—C13—C31128.57 (16)C33—C32—H32119.9
O6—C13—C31111.24 (14)C31—C32—H32119.9
O6—C21—C26122.21 (16)C34—C33—C32120.43 (19)
O6—C21—C22115.91 (16)C34—C33—H33119.8
C26—C21—C22121.87 (17)C32—C33—H33119.8
C23—C22—C21118.74 (18)C33—C34—C35119.96 (18)
C23—C22—H22120.6C33—C34—H34120.0
C21—C22—H22120.6C35—C34—H34120.0
C22—C23—C24120.64 (18)C34—C35—C36120.16 (18)
C22—C23—H23119.7C34—C35—H35119.9
C24—C23—H23119.7C36—C35—H35119.9
C25—C24—C23120.16 (18)C35—C36—C31120.32 (18)
C25—C24—H24119.9C35—C36—H36119.8
C23—C24—H24119.9C31—C36—H36119.8
C24—C25—C26120.21 (18)C12—O5—H5109.5
C24—C25—H25119.9C21—O6—C13121.00 (14)
C26—C25—H25119.9
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5···O40.842.242.6680 (19)112
O5—H5···O4i0.841.932.7022 (18)153
C36—H36···O60.952.302.656 (2)101
C32—H32···O50.952.192.852 (2)126
Symmetry code: (i) x1/2, y+3/2, z+1.
Selected bond lengths (Å) and angles (°) for the structures of 1, 3 and 4 top
134
Re1—C11.905 (3)Re1—C11.900 (4)C11—O41.238 (2)
Re1—C21.892 (3)Re1—C21.899 (4)C12—O51.350 (2)
Re1—C31.889 (3)Re1—C31.892 (4)C13—C311.474 (2)
Re1—Br12.6690 (5)Re1—O72.187 (3)C13—O61.370 (2)
Re1—O112.1292 (19)Re1—O42.128 (2)C21—O61.361 (2)
Re1—O122.1204 (19)Re1—O52.149 (2)
O11—Re1—O1276.78 (7)O4—Re1—O576.72 (9)O4—C11—C12119.48 (17)
C3—Re1—Br1177.92 (9)C3—Re1—O7174.51 (13)O5—C12—C11116.44 (16)
C3—Re1—O1194.10 (10)C3—Re1—O598.98 (12)C12—O5—H5109.5
Summary of the hydrogen-bond interactions and π-interactions observed in 1, 3 and 4 (Å, °) top
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···AD—HH···AD···AD—H···A
N1—H1···Br1a0.91 (4)2.52 (4)3.420 (2)170 (3)
C17—H17···O12a0.952.593.385 (3)142.1
C23—H23A···O12a0.992.413.388 (3)170.1
C25—H25A···O2b0.992.593.111 (3)112.5
C25—H25B···O1c0.992.573.520 (4)161.5
C26—H26A···O2d0.982.563.520 (4)166.1
C27—H27B···O3e0.992.403.286 (3)148.5
YX(I)Res(I)Cg(J)X···CgYX···CgY···Cg
C22—H22Ca[1] Cg22.7074 (4)137.86 (25)3.496 (5)
Re1—Br1[1] Cg12.9666 (12)36.575 (8)1.7908 (10)
3
D—H···AD—HH···AD···AD—H···A
O7—H7A···O04f0.65 (5)2.01 (5)2.641 (4)167 (6)
O7—H7B···O5g0.88 (6)1.81 (6)2.658 (4)162 (6)
C35—H35···O05h0.952.463.334 (4)153
O05—H05···O040.842.122.595 (3)115
C036—H036···O060.952.352.696 (4)101
C032—H032···O050.952.212.859 (4)125
C32—H32···O50.952.412.985 (4)119
YX(I)Res(I)Cg(J)X···CgYX···CgY···Cg
O7—H7A[1] Cg12.67 (5)57 (4)2.379 (4)
C1—O1i[1] Cg23.500 (3)110.7 (3)4.057 (4)
C2—O2i[1] Cg43.377 (4)92.5 (2)3.617 (5)
4
D—H···AD—HH···AD···AD—H···A
O5—H5···O40.822.252.668 (3)112
O4—H5···O4j0.821.942.703 (3)154
C36—H36···O60.932.312.657 (3)102
C32—H32···O50.932.202.853 (4)127
YX(I)Res(I)Cg(J)X···CgYX···CgY···Cg
C23—H23k[1] Cg22.9430 (8)1403.702 (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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