organic compounds
3,4-Dibromo-2,2,5,5-tetraphenyl-2,5-dihydrofuran
aInstitut für Organische Chemie, TU Bergakademie Freiberg, Leipziger Strasse 29, D-09596 Freiberg/Sachsen, Germany
*Correspondence e-mail: edwin.weber@chemie-tu.freiberg.de
The 28H20Br2O, was solved in the orthorhombic P212121 with one molecule in the The phenyl rings are nearly planar and inclined at angles of 67.7 (1), 68.8 (1), 79.3 (1) and 62.3 (1)° to the plane of the 2,5-dihydrofuran ring. The features C—H⋯π and Br⋯Br interactions, which connect the molecules to a three-dimensional supramolecular network.
of the title compound, CKeywords: hexasubstituted 2,5-dihydrofuran; crystal structure; C—H⋯π interaction; Br⋯Br contact.
CCDC reference: 1828960
Structure description
The title compound was obtained as an unexpected product in a bromination reaction of 1,1-diphenylprop-2-yne-1-ol in order to obtain 1,1-diphenyl-3-bromo-2-propyne-1-ol. Performance of this transformation using potassium hydroxide dissolved in water, bromine and 1,1-diphenyl-2-propyne-1-ol (Maraval et al., 2008) added as a solution in n-pentane at 273 K following conditions of a described procedure (Saalfrank et al., 1996) yielded the intended product. However, when applying the same synthesis but heating the reaction mixture to reflux for 12 h instead of stirring for 60 h at room temperature, the modified reaction condition surprisingly led to the formation of the title compound as the main product. Nevertheless, upon closer inspection of the circumstances, a potential course of the reaction may be assumed in a first step by base-induced abstraction of a proton from the starting compound (1,1-diphenylprop-2-yne-1-ol) to yield an equilibrium mixture of both corresponding alkoxide and acetylide species. Deprotonation of the acetylide species following a retro Favorskii-type reaction (Wuts & Greene, 2007) gives rise to the formation of diphenyl ketone as an intermediate, which on nucleophilic attack by the acetylide species may produce a mono-deprotonated acetylenic diol (1,1,4,4-tetraphenylbut-2-yne-1,4-diol) (Kostikov et al., 1996). Subsequent hydrolysis and addition of bromine may then give a dibromo-substituted secondary product (2,3-dibromo-1,1,4,4-tetraphenylbut-2-ene-1,4-diol), which finally via dehydration and ring closure reactions (Salkind & Teterin, 1929) ends up with the formation of the title compound. Crystals of this latter compound were used for X-ray analysis.
The ). The furan ring deviates slightly from planarity with maximum atomic distances from the the least-squares plane being −0.044 (2) Å for O1 and 0.042 (1) Å for C28. In addition, the aromatic rings are not perfectly planar. The maximum distances from the least-squares plane are 0.012 (2) and 0.015 (2) for atoms C1 and C6 of ring A. The phenyl rings A, B, C and D are inclined at angles of 67.7 (1), 68.8 (1), 79.3 (1) and 62.3 (1)°, respectively, to the plane of the 2,5-dihydrofuran ring.
contains one molecule (Fig. 1In the π interactions (Nishio et al. 2009) with the aromatic rings A and B acting as acceptors (Table 1, Fig. 2). Moreover, type I Br⋯Br contacts (Awwadi et al., 2006) [d(Br⋯Br) 3.814 (4) Å; θ1 = 136.0°, θ2 = 135.1°] connect the molecules into a three-dimensional supramolecular network.
molecules are connected by C—H⋯Synthesis and crystallization
To a solution of potassium hydroxide (5.46 g, 140 mmol) in water (26 ml), bromine (2.3 g, 13.91 mmol) was added at 277 K. 1,1-Diphenylprop-2-yne-1-ol (3.90 g, 18.72 mmol) dissolved in n-pentane (35 ml) was added dropwise at 273 K and the mixture was then heated to reflux for 12 h. After cooling and extraction with dichloromethane, the combined organic layers were washed with water, dried over sodium sulfate and evaporated. Crystallization from n-hexane yielded 6.9 g (70%) red crystals with m.p. 371 K. 1H NMR (500.1 MHz, CDCl3): δ = 7.21–7.35 (m, 20H, ArH) p.p.m.; 13C NMR (125.8 MHz, CDCl3): δ = 83.8 (C—O), 113.4 (C—Br), 127.5, 128.1, 129.3, 142.2 (Ar) p.p.m. Yellow scaly crystals were grown by slow evaporation of the solvent from a 1:1 solvent mixture of ethanol and THF.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1828960
https://doi.org/10.1107/S2414314618004169/sj4159sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618004169/sj4159Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314618004169/sj4159Isup3.cml
Data collection: APEX2 (Bruker, 2014); cell
SAINT-NT (Bruker, 2014); data reduction: SAINT-NT (Bruker, 2014); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008b).C28H20Br2O | Dx = 1.595 Mg m−3 |
Mr = 532.26 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 9991 reflections |
a = 9.4301 (5) Å | θ = 2.3–25.3° |
b = 9.4561 (5) Å | µ = 3.68 mm−1 |
c = 24.8572 (12) Å | T = 153 K |
V = 2216.6 (2) Å3 | Column, yellow |
Z = 4 | 0.43 × 0.24 × 0.09 mm |
F(000) = 1064 |
Bruker Kappa goniometer with an APEXII CCD area detector diffractometer | 4510 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.031 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a) | θmax = 27.1°, θmin = 3.1° |
Tmin = 0.301, Tmax = 0.733 | h = −12→12 |
39405 measured reflections | k = −12→12 |
4867 independent reflections | l = −31→31 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.022 | w = 1/[σ2(Fo2) + (0.0208P)2 + 0.686P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.047 | (Δ/σ)max = 0.002 |
S = 1.06 | Δρmax = 0.50 e Å−3 |
4867 reflections | Δρmin = −0.36 e Å−3 |
280 parameters | Absolute structure: Flack x determined using 1813 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
0 restraints | Absolute structure parameter: 0.014 (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 | ||
Br1 | 0.89406 (3) | 0.13600 (3) | 0.75235 (2) | 0.03301 (8) | |
Br2 | 0.81193 (4) | −0.16441 (3) | 0.67457 (2) | 0.04367 (10) | |
O1 | 0.72096 (19) | 0.21958 (19) | 0.60295 (8) | 0.0221 (4) | |
C1 | 0.8180 (3) | 0.0195 (3) | 0.55259 (11) | 0.0227 (5) | |
C2 | 0.9027 (3) | 0.1164 (3) | 0.52542 (11) | 0.0249 (6) | |
H2 | 0.8987 | 0.2137 | 0.5348 | 0.030* | |
C3 | 0.9935 (3) | 0.0718 (3) | 0.48454 (12) | 0.0287 (6) | |
H3 | 1.0505 | 0.1390 | 0.4661 | 0.034* | |
C4 | 1.0009 (3) | −0.0690 (4) | 0.47076 (13) | 0.0309 (7) | |
H4 | 1.0639 | −0.0994 | 0.4432 | 0.037* | |
C5 | 0.9164 (3) | −0.1659 (3) | 0.49715 (12) | 0.0350 (7) | |
H5 | 0.9220 | −0.2632 | 0.4879 | 0.042* | |
C6 | 0.8235 (3) | −0.1225 (3) | 0.53706 (11) | 0.0306 (6) | |
H6 | 0.7632 | −0.1897 | 0.5540 | 0.037* | |
C7 | 0.5668 (3) | 0.0223 (3) | 0.59101 (11) | 0.0242 (6) | |
C8 | 0.5012 (3) | 0.0558 (3) | 0.54270 (12) | 0.0256 (6) | |
H8 | 0.5553 | 0.0954 | 0.5142 | 0.031* | |
C9 | 0.3571 (3) | 0.0319 (3) | 0.53566 (13) | 0.0299 (7) | |
H9 | 0.3126 | 0.0586 | 0.5029 | 0.036* | |
C10 | 0.2784 (3) | −0.0302 (3) | 0.57589 (13) | 0.0334 (7) | |
H10 | 0.1800 | −0.0473 | 0.5709 | 0.040* | |
C11 | 0.3431 (4) | −0.0672 (4) | 0.62314 (14) | 0.0426 (9) | |
H11 | 0.2896 | −0.1114 | 0.6508 | 0.051* | |
C12 | 0.4873 (3) | −0.0405 (4) | 0.63092 (13) | 0.0367 (8) | |
H12 | 0.5309 | −0.0658 | 0.6640 | 0.044* | |
C13 | 0.9269 (3) | 0.3462 (3) | 0.63427 (10) | 0.0222 (5) | |
C14 | 1.0550 (3) | 0.2743 (3) | 0.63200 (12) | 0.0298 (7) | |
H14 | 1.0605 | 0.1793 | 0.6442 | 0.036* | |
C15 | 1.1751 (3) | 0.3406 (4) | 0.61195 (12) | 0.0347 (7) | |
H15 | 1.2620 | 0.2900 | 0.6098 | 0.042* | |
C16 | 1.1693 (3) | 0.4786 (4) | 0.59515 (12) | 0.0356 (7) | |
H16 | 1.2524 | 0.5241 | 0.5821 | 0.043* | |
C17 | 1.0433 (3) | 0.5508 (4) | 0.59718 (12) | 0.0336 (7) | |
H17 | 1.0391 | 0.6464 | 0.5855 | 0.040* | |
C18 | 0.9221 (3) | 0.4851 (3) | 0.61623 (11) | 0.0277 (6) | |
H18 | 0.8349 | 0.5354 | 0.6170 | 0.033* | |
C19 | 0.6891 (3) | 0.3723 (3) | 0.68066 (10) | 0.0228 (5) | |
C20 | 0.5465 (3) | 0.3771 (3) | 0.66836 (12) | 0.0305 (6) | |
H20 | 0.5084 | 0.3145 | 0.6422 | 0.037* | |
C21 | 0.4587 (3) | 0.4733 (4) | 0.69428 (13) | 0.0411 (8) | |
H21 | 0.3604 | 0.4754 | 0.6860 | 0.049* | |
C22 | 0.5128 (4) | 0.5661 (4) | 0.73193 (13) | 0.0390 (8) | |
H22 | 0.4530 | 0.6346 | 0.7483 | 0.047* | |
C23 | 0.6546 (3) | 0.5585 (3) | 0.74557 (13) | 0.0343 (7) | |
H23 | 0.6917 | 0.6194 | 0.7725 | 0.041* | |
C24 | 0.7425 (3) | 0.4628 (3) | 0.72030 (11) | 0.0275 (6) | |
H24 | 0.8399 | 0.4582 | 0.7299 | 0.033* | |
C25 | 0.7222 (3) | 0.0655 (3) | 0.59914 (11) | 0.0226 (6) | |
C26 | 0.7833 (3) | 0.0246 (3) | 0.65326 (12) | 0.0252 (6) | |
C27 | 0.8166 (3) | 0.1362 (3) | 0.68208 (10) | 0.0246 (5) | |
C28 | 0.7898 (3) | 0.2722 (3) | 0.65141 (11) | 0.0213 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.02996 (13) | 0.03975 (17) | 0.02930 (14) | 0.00078 (13) | −0.01210 (13) | 0.00297 (15) |
Br2 | 0.0640 (2) | 0.02275 (15) | 0.04424 (18) | 0.00568 (16) | −0.01158 (17) | 0.00825 (14) |
O1 | 0.0226 (10) | 0.0183 (9) | 0.0254 (10) | −0.0006 (7) | −0.0052 (8) | −0.0013 (8) |
C1 | 0.0222 (13) | 0.0213 (13) | 0.0246 (14) | 0.0017 (12) | −0.0060 (11) | 0.0013 (11) |
C2 | 0.0244 (13) | 0.0213 (14) | 0.0289 (14) | 0.0016 (12) | −0.0047 (12) | −0.0024 (11) |
C3 | 0.0237 (15) | 0.0326 (16) | 0.0297 (16) | −0.0018 (12) | −0.0023 (12) | −0.0014 (12) |
C4 | 0.0233 (16) | 0.0391 (18) | 0.0303 (17) | 0.0071 (14) | −0.0012 (12) | −0.0045 (13) |
C5 | 0.0416 (17) | 0.0240 (15) | 0.0394 (17) | 0.0099 (14) | −0.0092 (14) | −0.0064 (13) |
C6 | 0.0338 (15) | 0.0228 (14) | 0.0352 (16) | −0.0004 (13) | −0.0035 (13) | −0.0002 (12) |
C7 | 0.0239 (14) | 0.0201 (14) | 0.0285 (15) | −0.0018 (11) | −0.0025 (11) | −0.0039 (11) |
C8 | 0.0256 (15) | 0.0211 (15) | 0.0301 (16) | −0.0004 (12) | 0.0000 (12) | 0.0002 (12) |
C9 | 0.0265 (15) | 0.0269 (16) | 0.0364 (17) | 0.0018 (12) | −0.0075 (12) | −0.0015 (13) |
C10 | 0.0216 (15) | 0.0390 (19) | 0.0397 (18) | −0.0056 (13) | 0.0001 (13) | −0.0111 (14) |
C11 | 0.0357 (18) | 0.058 (2) | 0.0344 (18) | −0.0193 (16) | 0.0068 (14) | −0.0028 (16) |
C12 | 0.0346 (17) | 0.049 (2) | 0.0266 (17) | −0.0114 (15) | −0.0028 (13) | 0.0017 (14) |
C13 | 0.0195 (12) | 0.0250 (14) | 0.0222 (13) | −0.0029 (11) | −0.0006 (9) | −0.0058 (12) |
C14 | 0.0253 (15) | 0.0289 (16) | 0.0351 (17) | 0.0013 (12) | −0.0022 (12) | −0.0059 (13) |
C15 | 0.0189 (13) | 0.0455 (19) | 0.0398 (17) | 0.0019 (15) | 0.0009 (12) | −0.0100 (15) |
C16 | 0.0250 (15) | 0.051 (2) | 0.0309 (17) | −0.0106 (15) | 0.0055 (13) | −0.0035 (14) |
C17 | 0.0367 (17) | 0.0339 (18) | 0.0303 (17) | −0.0051 (14) | 0.0049 (14) | 0.0048 (13) |
C18 | 0.0253 (15) | 0.0320 (16) | 0.0258 (15) | 0.0004 (12) | 0.0019 (11) | 0.0013 (12) |
C19 | 0.0222 (12) | 0.0238 (13) | 0.0222 (12) | −0.0036 (12) | −0.0002 (11) | 0.0028 (11) |
C20 | 0.0252 (13) | 0.0380 (17) | 0.0283 (15) | 0.0018 (12) | −0.0022 (12) | −0.0062 (14) |
C21 | 0.0248 (15) | 0.060 (2) | 0.0387 (18) | 0.0095 (16) | −0.0014 (13) | −0.0068 (16) |
C22 | 0.0375 (18) | 0.046 (2) | 0.0339 (18) | 0.0114 (15) | 0.0093 (14) | −0.0067 (14) |
C23 | 0.0403 (16) | 0.0347 (16) | 0.0280 (16) | −0.0054 (13) | 0.0053 (14) | −0.0054 (14) |
C24 | 0.0240 (14) | 0.0319 (17) | 0.0266 (15) | −0.0056 (12) | 0.0003 (12) | −0.0007 (13) |
C25 | 0.0246 (14) | 0.0178 (13) | 0.0255 (15) | −0.0018 (11) | −0.0035 (12) | −0.0004 (11) |
C26 | 0.0239 (14) | 0.0208 (14) | 0.0310 (15) | 0.0001 (11) | −0.0008 (12) | 0.0057 (11) |
C27 | 0.0202 (12) | 0.0279 (14) | 0.0257 (13) | −0.0011 (12) | −0.0036 (11) | 0.0032 (12) |
C28 | 0.0199 (13) | 0.0219 (13) | 0.0222 (13) | −0.0021 (11) | −0.0036 (11) | −0.0020 (11) |
Br1—C27 | 1.894 (3) | C13—C14 | 1.387 (4) |
Br2—C26 | 1.884 (3) | C13—C18 | 1.389 (4) |
O1—C28 | 1.456 (3) | C13—C28 | 1.530 (4) |
O1—C25 | 1.460 (3) | C14—C15 | 1.387 (4) |
C1—C2 | 1.390 (4) | C14—H14 | 0.9500 |
C1—C6 | 1.399 (4) | C15—C16 | 1.372 (5) |
C1—C25 | 1.531 (4) | C15—H15 | 0.9500 |
C2—C3 | 1.394 (4) | C16—C17 | 1.371 (5) |
C2—H2 | 0.9500 | C16—H16 | 0.9500 |
C3—C4 | 1.377 (5) | C17—C18 | 1.385 (4) |
C3—H3 | 0.9500 | C17—H17 | 0.9500 |
C4—C5 | 1.380 (5) | C18—H18 | 0.9500 |
C4—H4 | 0.9500 | C19—C20 | 1.379 (4) |
C5—C6 | 1.386 (4) | C19—C24 | 1.399 (4) |
C5—H5 | 0.9500 | C19—C28 | 1.526 (4) |
C6—H6 | 0.9500 | C20—C21 | 1.389 (4) |
C7—C12 | 1.378 (4) | C20—H20 | 0.9500 |
C7—C8 | 1.388 (4) | C21—C22 | 1.380 (5) |
C7—C25 | 1.535 (4) | C21—H21 | 0.9500 |
C8—C9 | 1.388 (4) | C22—C23 | 1.381 (4) |
C8—H8 | 0.9500 | C22—H22 | 0.9500 |
C9—C10 | 1.377 (4) | C23—C24 | 1.379 (4) |
C9—H9 | 0.9500 | C23—H23 | 0.9500 |
C10—C11 | 1.369 (5) | C24—H24 | 0.9500 |
C10—H10 | 0.9500 | C25—C26 | 1.514 (4) |
C11—C12 | 1.396 (4) | C26—C27 | 1.313 (4) |
C11—H11 | 0.9500 | C27—C28 | 1.517 (4) |
C12—H12 | 0.9500 | ||
C28—O1—C25 | 113.0 (2) | C17—C16—C15 | 119.8 (3) |
C2—C1—C6 | 118.5 (3) | C17—C16—H16 | 120.1 |
C2—C1—C25 | 121.3 (2) | C15—C16—H16 | 120.1 |
C6—C1—C25 | 120.2 (3) | C16—C17—C18 | 120.3 (3) |
C1—C2—C3 | 120.5 (3) | C16—C17—H17 | 119.9 |
C1—C2—H2 | 119.7 | C18—C17—H17 | 119.9 |
C3—C2—H2 | 119.7 | C17—C18—C13 | 120.5 (3) |
C4—C3—C2 | 120.3 (3) | C17—C18—H18 | 119.7 |
C4—C3—H3 | 119.8 | C13—C18—H18 | 119.7 |
C2—C3—H3 | 119.8 | C20—C19—C24 | 119.1 (3) |
C3—C4—C5 | 119.6 (3) | C20—C19—C28 | 121.5 (2) |
C3—C4—H4 | 120.2 | C24—C19—C28 | 119.4 (2) |
C5—C4—H4 | 120.2 | C19—C20—C21 | 120.0 (3) |
C4—C5—C6 | 120.6 (3) | C19—C20—H20 | 120.0 |
C4—C5—H5 | 119.7 | C21—C20—H20 | 120.0 |
C6—C5—H5 | 119.7 | C22—C21—C20 | 120.7 (3) |
C5—C6—C1 | 120.3 (3) | C22—C21—H21 | 119.6 |
C5—C6—H6 | 119.8 | C20—C21—H21 | 119.6 |
C1—C6—H6 | 119.8 | C21—C22—C23 | 119.4 (3) |
C12—C7—C8 | 118.6 (3) | C21—C22—H22 | 120.3 |
C12—C7—C25 | 122.6 (3) | C23—C22—H22 | 120.3 |
C8—C7—C25 | 118.6 (3) | C24—C23—C22 | 120.3 (3) |
C7—C8—C9 | 120.5 (3) | C24—C23—H23 | 119.9 |
C7—C8—H8 | 119.7 | C22—C23—H23 | 119.9 |
C9—C8—H8 | 119.7 | C23—C24—C19 | 120.4 (3) |
C10—C9—C8 | 120.4 (3) | C23—C24—H24 | 119.8 |
C10—C9—H9 | 119.8 | C19—C24—H24 | 119.8 |
C8—C9—H9 | 119.8 | O1—C25—C26 | 101.5 (2) |
C11—C10—C9 | 119.4 (3) | O1—C25—C1 | 109.7 (2) |
C11—C10—H10 | 120.3 | C26—C25—C1 | 112.0 (2) |
C9—C10—H10 | 120.3 | O1—C25—C7 | 105.5 (2) |
C10—C11—C12 | 120.5 (3) | C26—C25—C7 | 114.3 (2) |
C10—C11—H11 | 119.8 | C1—C25—C7 | 112.9 (2) |
C12—C11—H11 | 119.8 | C27—C26—C25 | 111.8 (2) |
C7—C12—C11 | 120.5 (3) | C27—C26—Br2 | 125.1 (2) |
C7—C12—H12 | 119.7 | C25—C26—Br2 | 123.1 (2) |
C11—C12—H12 | 119.7 | C26—C27—C28 | 111.6 (2) |
C14—C13—C18 | 118.6 (3) | C26—C27—Br1 | 126.5 (2) |
C14—C13—C28 | 121.5 (3) | C28—C27—Br1 | 121.91 (19) |
C18—C13—C28 | 119.6 (2) | O1—C28—C27 | 101.5 (2) |
C13—C14—C15 | 120.3 (3) | O1—C28—C19 | 109.2 (2) |
C13—C14—H14 | 119.9 | C27—C28—C19 | 113.0 (2) |
C15—C14—H14 | 119.9 | O1—C28—C13 | 107.6 (2) |
C16—C15—C14 | 120.4 (3) | C27—C28—C13 | 112.8 (2) |
C16—C15—H15 | 119.8 | C19—C28—C13 | 112.1 (2) |
C14—C15—H15 | 119.8 | ||
C6—C1—C2—C3 | −1.5 (4) | C2—C1—C25—C7 | 125.6 (3) |
C25—C1—C2—C3 | 177.5 (2) | C6—C1—C25—C7 | −55.4 (3) |
C1—C2—C3—C4 | −0.4 (4) | C12—C7—C25—O1 | −106.8 (3) |
C2—C3—C4—C5 | 0.9 (4) | C8—C7—C25—O1 | 69.0 (3) |
C3—C4—C5—C6 | 0.5 (5) | C12—C7—C25—C26 | 3.9 (4) |
C4—C5—C6—C1 | −2.5 (5) | C8—C7—C25—C26 | 179.7 (2) |
C2—C1—C6—C5 | 2.9 (4) | C12—C7—C25—C1 | 133.5 (3) |
C25—C1—C6—C5 | −176.1 (3) | C8—C7—C25—C1 | −50.7 (3) |
C12—C7—C8—C9 | 2.6 (4) | O1—C25—C26—C27 | −2.3 (3) |
C25—C7—C8—C9 | −173.3 (3) | C1—C25—C26—C27 | 114.7 (3) |
C7—C8—C9—C10 | −2.4 (5) | C7—C25—C26—C27 | −115.3 (3) |
C8—C9—C10—C11 | 0.6 (5) | O1—C25—C26—Br2 | 179.54 (18) |
C9—C10—C11—C12 | 0.9 (5) | C1—C25—C26—Br2 | −63.5 (3) |
C8—C7—C12—C11 | −1.2 (5) | C7—C25—C26—Br2 | 66.5 (3) |
C25—C7—C12—C11 | 174.7 (3) | C25—C26—C27—C28 | −2.5 (3) |
C10—C11—C12—C7 | −0.6 (5) | Br2—C26—C27—C28 | 175.6 (2) |
C18—C13—C14—C15 | −0.1 (4) | C25—C26—C27—Br1 | 179.32 (19) |
C28—C13—C14—C15 | 174.5 (3) | Br2—C26—C27—Br1 | −2.5 (4) |
C13—C14—C15—C16 | 1.3 (5) | C25—O1—C28—C27 | −7.8 (3) |
C14—C15—C16—C17 | −1.3 (5) | C25—O1—C28—C19 | −127.3 (2) |
C15—C16—C17—C18 | 0.2 (5) | C25—O1—C28—C13 | 110.9 (2) |
C16—C17—C18—C13 | 1.0 (5) | C26—C27—C28—O1 | 6.2 (3) |
C14—C13—C18—C17 | −1.0 (4) | Br1—C27—C28—O1 | −175.57 (17) |
C28—C13—C18—C17 | −175.7 (3) | C26—C27—C28—C19 | 123.0 (3) |
C24—C19—C20—C21 | 1.6 (4) | Br1—C27—C28—C19 | −58.8 (3) |
C28—C19—C20—C21 | −177.5 (3) | C26—C27—C28—C13 | −108.7 (3) |
C19—C20—C21—C22 | 0.8 (5) | Br1—C27—C28—C13 | 69.5 (3) |
C20—C21—C22—C23 | −2.9 (5) | C20—C19—C28—O1 | 15.0 (3) |
C21—C22—C23—C24 | 2.5 (5) | C24—C19—C28—O1 | −164.0 (2) |
C22—C23—C24—C19 | −0.1 (5) | C20—C19—C28—C27 | −97.1 (3) |
C20—C19—C24—C23 | −2.0 (4) | C24—C19—C28—C27 | 83.8 (3) |
C28—C19—C24—C23 | 177.1 (3) | C20—C19—C28—C13 | 134.2 (3) |
C28—O1—C25—C26 | 6.5 (3) | C24—C19—C28—C13 | −44.9 (3) |
C28—O1—C25—C1 | −112.2 (2) | C14—C13—C28—O1 | −92.0 (3) |
C28—O1—C25—C7 | 126.0 (2) | C18—C13—C28—O1 | 82.5 (3) |
C2—C1—C25—O1 | 8.3 (4) | C14—C13—C28—C27 | 19.1 (4) |
C6—C1—C25—O1 | −172.7 (2) | C18—C13—C28—C27 | −166.3 (2) |
C2—C1—C25—C26 | −103.6 (3) | C14—C13—C28—C19 | 147.9 (2) |
C6—C1—C25—C26 | 75.4 (3) | C18—C13—C28—C19 | −37.5 (3) |
Cg2 and Cg3 are the centroids of the C1–C6 and C7–C12 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···Cg2i | 0.95 | 2.82 | 3.701 (3) | 155 |
C10—H10···Cg1ii | 0.95 | 2.96 | 3.835 (3) | 154 |
C16—H16···Cg1iii | 0.95 | 2.75 | 3.508 (3) | 137 |
Symmetry codes: (i) −x, y−1/2, −z+3/2; (ii) x−1, y, z; (iii) −x, y+1/2, −z+3/2. |
Funding information
We acknowledge the financial support by the Deutsche Forschungsgemeinschaft (DFG Priority Program 1362 `Porous Metal-Organic Frameworks').
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