3,4-Di­bromo-2,2,5,5-tetra­phenyl-2,5-di­hydro­furan

Seidel, N.; Seichter, W.; Weber, E.

doi:10.1107/S2414314618004169

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 3| Part 4| April 2018| x180416

https://doi.org/10.1107/S2414314618004169

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3,4-Dibromo-2,2,5,5-tetraphenyl-2,5-dihydrofuran

Nadine Seidel,^a Wilhelm Seichter ^a and Edwin Weber ^a ^*

^aInstitut für Organische Chemie, TU Bergakademie Freiberg, Leipziger Strasse 29, D-09596 Freiberg/Sachsen, Germany
^*Correspondence e-mail: edwin.weber@chemie-tu.freiberg.de

Edited by J. Simpson, University of Otago, New Zealand (Received 5 February 2018; accepted 12 March 2018; online 6 April 2018)

The crystal structure of the title compound, C₂₈H₂₀Br₂O, was solved in the orthorhombic space group P2₁2₁2₁ with one molecule in the asymmetric unit. 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 crystal structure features C—H⋯π and Br⋯Br interactions, which connect the molecules to a three-dimensional supramolecular network.

Keywords: 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 crystal structure analysis.

The asymmetric unit contains one molecule (Fig. 1). 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.

Figure 1
Perspective view of the title compound including atom labelling and ring specification. Non-hydrogen atoms are shown with 50% probability displacement ellipsoids.

In the crystal structure, molecules are connected by C—H⋯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.

Table 1
Hydrogen-bond geometry (Å, °)

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) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) x-1, y, z; (iii) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Figure 2
Part of the packing of the title compound viewed along the a-axis. Oxygen atoms are displayed as dotted circles (red) and bromine atoms as cross-hatched circles. The intermolecular contacts are shown as dashed lines.

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 refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₈H₂₀Br₂O
M_r	532.26
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	153
a, b, c (Å)	9.4301 (5), 9.4561 (5), 24.8572 (12)
V (Å³)	2216.6 (2)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	3.68
Crystal size (mm)	0.43 × 0.24 × 0.09

Data collection
Diffractometer	Bruker Kappa goniometer with an APEXII CCD area detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2008a )
T_min, T_max	0.301, 0.733
No. of measured, independent and observed [I > 2σ(I)] reflections	39405, 4867, 4510
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.641

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.022, 0.047, 1.06
No. of reflections	4867
No. of parameters	280
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.36
Absolute structure	Flack x determined using 1813 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	0.014 (3)
Computer programs: APEX2 and SAINT-NT (Bruker, 2014 ), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ) and SHELXTL (Sheldrick, 2008b ).

Structural data

CCDC reference: 1828960

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314618004169/sj4159sup1.cif

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

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: 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).

3,4-Dibromo-2,2,5,5-tetraphenyl-2,5-dihydrofuran top

Crystal data top

C₂₈H₂₀Br₂O	D_x = 1.595 Mg m⁻³
M_r = 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

Data collection top

Bruker Kappa goniometer with an APEXII CCD area detector diffractometer	4510 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.031
Absorption correction: multi-scan (SADABS; Sheldrick, 2008a)	θ_max = 27.1°, θ_min = 3.1°
T_min = 0.301, T_max = 0.733	h = −12→12
39405 measured reflections	k = −12→12
4867 independent reflections	l = −31→31

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.022	w = 1/[σ²(F_o²) + (0.0208P)² + 0.686P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.047	(Δ/σ)_max = 0.002
S = 1.06	Δρ_max = 0.50 e Å⁻³
4867 reflections	Δρ_min = −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)

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	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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').

References

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Volume 3| Part 4| April 2018| x180416

https://doi.org/10.1107/S2414314618004169

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3,4-Di­bromo-2,2,5,5-tetra­phenyl-2,5-di­hydro­furan

Structure description

Synthesis and crystallization

Refinement

Structural data

Funding information

References

organic compounds

3,4-Dibromo-2,2,5,5-tetraphenyl-2,5-dihydrofuran