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1,5-Bis([1,1′-biphen­yl]-4-yl)-5-hy­droxy-3-methyl­heptane-1,6-dione, C32H30O3, was investigated by X-ray analysis, quantum chemical calculations and AIM (atoms in mol­ecules) analysis. It was shown that four intra­molecular C—H...π forces are established between the two biphenyl fragments. C—H...π inter­actions lead to a bending of the biphenyl part. The energy of the intra­molecular inter­actions was estimated and the exclusive role of the moment of force was established.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619012567/fn3321sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619012567/fn3321Isup2.hkl
Contains datablock I

cml

Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229619012567/fn3321Isup3.cml
Supplementary material

CCDC reference: 1952577

Computing details top

Data collection: SAINT (Bruker, 2017); cell refinement: APEX3 (Bruker, 2017); data reduction: SAINT (Bruker, 2017); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2008).

(I) top
Crystal data top
C32H30O3Z = 2
Mr = 462.56F(000) = 492
Triclinic, P1Dx = 1.248 Mg m3
a = 5.954 (16) ÅMo Kα radiation, λ = 0.71073 Å
b = 7.88 (2) ÅCell parameters from 539 reflections
c = 26.30 (7) Åθ = 2.5–25.1°
α = 89.56 (7)°µ = 0.08 mm1
β = 86.85 (6)°T = 100 K
γ = 87.68 (6)°Prism, clear light colourless
V = 1231 (6) Å30.38 × 0.12 × 0.08 mm
Data collection top
Bruker D8 Venture Photon 100 CMOS
diffractometer
5226 independent reflections
Radiation source: IuS4335 reflections with I > 2σ(I)
No monochromatorRint = 0.065
Detector resolution: 0.79 pixels mm-1θmax = 26.8°, θmin = 2.3°
ω and φ scansh = 77
Absorption correction: multi-scan
(SADABS; Bruker, 2017)
k = 99
Tmin = 0.702, Tmax = 0.745l = 3333
54736 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullHydrogen site location: mixed
R[F2 > 2σ(F2)] = 0.048H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.131 w = 1/[σ2(Fo2) + (0.0595P)2 + 0.6514P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.004
5226 reflectionsΔρmax = 0.31 e Å3
321 parametersΔρmin = 0.37 e Å3
0 restraints
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
O10.11500 (17)0.59036 (15)0.08376 (5)0.0340 (3)
O20.89890 (18)0.12003 (15)0.13185 (4)0.0308 (3)
O30.45100 (16)0.67774 (12)0.05605 (4)0.0195 (2)
H30.582 (3)0.637 (2)0.0638 (7)0.029*
C10.4885 (4)0.7109 (3)0.40948 (7)0.0457 (5)
H10.5190640.7139650.4445310.055*
C20.3032 (4)0.6288 (3)0.39392 (7)0.0517 (5)
H20.2074580.5735790.4183370.062*
C30.2562 (3)0.6269 (3)0.34244 (6)0.0417 (4)
H3A0.1269800.5715090.3324400.050*
C40.3952 (3)0.70461 (18)0.30538 (6)0.0246 (3)
C50.3504 (2)0.69506 (17)0.24985 (5)0.0210 (3)
C60.1686 (2)0.6067 (2)0.23274 (6)0.0263 (3)
H60.0622210.5620510.2570130.032*
C70.1407 (2)0.58299 (19)0.18109 (5)0.0239 (3)
H70.0154400.5231600.1708750.029*
C80.2937 (2)0.64567 (16)0.14392 (5)0.0167 (3)
C90.2845 (2)0.59661 (16)0.08728 (5)0.0161 (3)
C100.2943 (2)0.40066 (17)0.07844 (5)0.0178 (3)
H10A0.1686290.3528000.0994190.021*
H10B0.2630330.3817640.0423800.021*
C110.5107 (2)0.29412 (17)0.08956 (5)0.0179 (3)
H110.6425030.3458150.0710280.021*
C120.5520 (2)0.28629 (18)0.14674 (5)0.0227 (3)
H12A0.5561940.4042520.1592750.027*
H12B0.4210710.2337640.1644980.027*
C130.7637 (2)0.19030 (17)0.16233 (5)0.0203 (3)
C140.8094 (2)0.19095 (17)0.21833 (5)0.0205 (3)
C151.0030 (3)0.1047 (2)0.23466 (6)0.0277 (3)
H151.0991330.0425180.2108400.033*
C161.0557 (3)0.1095 (2)0.28562 (6)0.0317 (4)
H161.1882920.0506010.2958400.038*
C170.9184 (3)0.19882 (19)0.32221 (6)0.0260 (3)
C180.9749 (3)0.2060 (2)0.37702 (6)0.0312 (4)
C191.1674 (5)0.1275 (3)0.39442 (8)0.0677 (8)
H191.2679520.0669230.3711330.081*
C201.2177 (5)0.1354 (4)0.44565 (9)0.0771 (9)
H201.3524580.0813020.4564810.092*
C211.0763 (4)0.2194 (3)0.48023 (8)0.0583 (6)
H211.1076290.2196500.5152640.070*
C220.6286 (4)0.7882 (3)0.37356 (7)0.0482 (5)
H220.7572800.8435540.3838770.058*
C230.5821 (3)0.7855 (3)0.32210 (7)0.0401 (4)
H230.6797450.8399610.2979000.048*
C240.0542 (2)0.66209 (17)0.06869 (5)0.0183 (3)
C250.0441 (2)0.8097 (2)0.03301 (6)0.0284 (3)
H25A0.1122030.8334630.0244110.043*
H25B0.1365540.7832050.0018890.043*
H25C0.1012590.9096380.0492530.043*
C260.4818 (3)0.11474 (18)0.06834 (6)0.0250 (3)
H26A0.6183960.0442720.0733030.038*
H26B0.4558570.1228030.0319160.038*
H26C0.3528780.0631970.0863310.038*
C270.8375 (4)0.2960 (4)0.41242 (8)0.0761 (9)
H270.7053910.3541510.4016490.091*
C280.8882 (5)0.3034 (5)0.46354 (9)0.0871 (10)
H280.7915740.3671210.4868850.104*
C290.7243 (3)0.2826 (2)0.30556 (6)0.0375 (4)
H290.6270460.3437140.3294110.045*
C300.6705 (3)0.2785 (2)0.25466 (6)0.0342 (4)
H300.5369510.3362400.2445150.041*
C310.4657 (2)0.74429 (18)0.16047 (5)0.0220 (3)
H310.5647370.7964670.1360720.026*
C320.4939 (3)0.76713 (19)0.21236 (6)0.0257 (3)
H320.6135370.8332830.2224600.031*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0122 (5)0.0412 (7)0.0490 (7)0.0047 (4)0.0060 (5)0.0163 (5)
O20.0241 (5)0.0410 (6)0.0262 (5)0.0097 (5)0.0001 (4)0.0006 (5)
O30.0101 (4)0.0255 (5)0.0228 (5)0.0014 (4)0.0014 (4)0.0070 (4)
C10.0565 (12)0.0588 (12)0.0227 (8)0.0011 (10)0.0114 (8)0.0046 (8)
C20.0602 (13)0.0718 (14)0.0241 (9)0.0169 (11)0.0019 (8)0.0031 (9)
C30.0452 (10)0.0569 (12)0.0244 (8)0.0168 (9)0.0029 (7)0.0001 (8)
C40.0279 (8)0.0221 (7)0.0235 (7)0.0042 (6)0.0029 (6)0.0031 (6)
C50.0225 (7)0.0187 (7)0.0218 (7)0.0028 (5)0.0016 (5)0.0024 (5)
C60.0204 (7)0.0348 (8)0.0235 (7)0.0055 (6)0.0035 (6)0.0005 (6)
C70.0162 (6)0.0308 (8)0.0252 (7)0.0063 (6)0.0008 (5)0.0007 (6)
C80.0134 (6)0.0153 (6)0.0213 (7)0.0023 (5)0.0028 (5)0.0008 (5)
C90.0106 (6)0.0185 (6)0.0193 (6)0.0013 (5)0.0018 (5)0.0033 (5)
C100.0149 (6)0.0198 (7)0.0191 (6)0.0025 (5)0.0044 (5)0.0006 (5)
C110.0161 (6)0.0173 (6)0.0205 (6)0.0005 (5)0.0019 (5)0.0004 (5)
C120.0228 (7)0.0233 (7)0.0219 (7)0.0056 (6)0.0049 (5)0.0025 (5)
C130.0187 (7)0.0174 (6)0.0248 (7)0.0009 (5)0.0020 (5)0.0021 (5)
C140.0203 (7)0.0180 (6)0.0234 (7)0.0009 (5)0.0031 (5)0.0030 (5)
C150.0225 (7)0.0324 (8)0.0274 (8)0.0069 (6)0.0011 (6)0.0030 (6)
C160.0237 (8)0.0414 (9)0.0297 (8)0.0083 (7)0.0066 (6)0.0049 (7)
C170.0283 (8)0.0245 (7)0.0257 (7)0.0021 (6)0.0064 (6)0.0025 (6)
C180.0358 (9)0.0333 (8)0.0256 (8)0.0061 (7)0.0081 (7)0.0036 (6)
C190.0842 (17)0.0793 (16)0.0392 (11)0.0431 (14)0.0310 (11)0.0160 (11)
C200.100 (2)0.0869 (18)0.0451 (13)0.0391 (16)0.0419 (13)0.0106 (12)
C210.0713 (15)0.0796 (16)0.0265 (9)0.0125 (12)0.0183 (10)0.0046 (10)
C220.0480 (11)0.0655 (13)0.0333 (10)0.0129 (10)0.0152 (8)0.0039 (9)
C230.0396 (10)0.0530 (11)0.0292 (9)0.0122 (8)0.0074 (7)0.0004 (8)
C240.0135 (6)0.0212 (7)0.0207 (6)0.0005 (5)0.0043 (5)0.0026 (5)
C250.0192 (7)0.0295 (8)0.0371 (8)0.0002 (6)0.0099 (6)0.0097 (6)
C260.0278 (8)0.0194 (7)0.0280 (7)0.0006 (6)0.0036 (6)0.0036 (6)
C270.0483 (13)0.149 (3)0.0291 (10)0.0287 (15)0.0095 (9)0.0165 (13)
C280.0602 (15)0.171 (3)0.0293 (11)0.0173 (18)0.0052 (10)0.0208 (15)
C290.0417 (10)0.0431 (10)0.0266 (8)0.0186 (8)0.0052 (7)0.0056 (7)
C300.0313 (8)0.0418 (9)0.0287 (8)0.0187 (7)0.0077 (7)0.0023 (7)
C310.0222 (7)0.0206 (7)0.0236 (7)0.0063 (5)0.0009 (5)0.0017 (5)
C320.0279 (8)0.0238 (7)0.0265 (7)0.0087 (6)0.0054 (6)0.0020 (6)
Geometric parameters (Å, º) top
O1—C241.221 (3)C14—C301.396 (3)
O2—C131.223 (3)C15—H150.9500
O3—H30.86 (2)C15—C161.394 (4)
O3—C91.421 (3)C16—H160.9500
C1—H10.9500C16—C171.403 (3)
C1—C21.383 (4)C17—C181.500 (4)
C1—C221.380 (4)C17—C291.397 (4)
C2—H20.9500C18—C191.379 (4)
C2—C31.398 (4)C18—C271.385 (4)
C3—H3A0.9500C19—H190.9500
C3—C41.398 (3)C19—C201.399 (4)
C4—C51.502 (4)C20—H200.9500
C4—C231.397 (4)C20—C211.361 (4)
C5—C61.407 (3)C21—H210.9500
C5—C321.401 (3)C21—C281.370 (5)
C6—H60.9500C22—H220.9500
C6—C71.392 (4)C22—C231.397 (4)
C7—H70.9500C23—H230.9500
C7—C81.400 (3)C24—C251.490 (4)
C8—C91.547 (4)C25—H25A0.9800
C8—C311.400 (3)C25—H25B0.9800
C9—C101.561 (5)C25—H25C0.9800
C9—C241.548 (4)C26—H26A0.9800
C10—H10A0.9900C26—H26B0.9800
C10—H10B0.9900C26—H26C0.9800
C10—C111.549 (4)C27—H270.9500
C11—H111.0000C27—C281.396 (4)
C11—C121.537 (4)C28—H280.9500
C11—C261.543 (4)C29—H290.9500
C12—H12A0.9900C29—C301.395 (4)
C12—H12B0.9900C30—H300.9500
C12—C131.518 (4)C31—H310.9500
C13—C141.513 (4)C31—C321.398 (4)
C14—C151.400 (3)C32—H320.9500
C9—O3—H3108.4 (12)C15—C16—H16119.1
C2—C1—H1120.3C15—C16—C17121.83 (19)
C22—C1—H1120.3C17—C16—H16119.1
C22—C1—C2119.3 (2)C16—C17—C18122.18 (19)
C1—C2—H2119.8C29—C17—C16117.2 (2)
C1—C2—C3120.32 (19)C29—C17—C18120.66 (16)
C3—C2—H2119.8C19—C18—C17122.04 (18)
C2—C3—H3A119.3C19—C18—C27116.8 (2)
C4—C3—C2121.4 (2)C27—C18—C17121.2 (2)
C4—C3—H3A119.3C18—C19—H19119.3
C3—C4—C5121.27 (19)C18—C19—C20121.3 (2)
C3—C4—C23117.1 (2)C20—C19—H19119.3
C23—C4—C5121.62 (15)C19—C20—H20119.5
C6—C5—C4121.72 (14)C21—C20—C19121.0 (3)
C32—C5—C4121.56 (19)C21—C20—H20119.5
C32—C5—C6116.7 (2)C20—C21—H21120.6
C5—C6—H6119.2C20—C21—C28118.7 (2)
C7—C6—C5121.62 (14)C28—C21—H21120.6
C7—C6—H6119.2C1—C22—H22119.8
C6—C7—H7119.4C1—C22—C23120.3 (2)
C6—C7—C8121.24 (19)C23—C22—H22119.8
C8—C7—H7119.4C4—C23—H23119.2
C7—C8—C9121.34 (17)C22—C23—C4121.55 (18)
C7—C8—C31117.4 (2)C22—C23—H23119.2
C31—C8—C9121.08 (13)O1—C24—C9118.7 (2)
O3—C9—C8111.96 (16)O1—C24—C25121.71 (16)
O3—C9—C10111.28 (15)C25—C24—C9119.60 (14)
O3—C9—C24106.2 (2)C24—C25—H25A109.5
C8—C9—C10113.34 (12)C24—C25—H25B109.5
C8—C9—C24107.83 (13)C24—C25—H25C109.5
C24—C9—C10105.72 (13)H25A—C25—H25B109.5
C9—C10—H10A107.4H25A—C25—H25C109.5
C9—C10—H10B107.4H25B—C25—H25C109.5
H10A—C10—H10B106.9C11—C26—H26A109.5
C11—C10—C9119.81 (15)C11—C26—H26B109.5
C11—C10—H10A107.4C11—C26—H26C109.5
C11—C10—H10B107.4H26A—C26—H26B109.5
C10—C11—H11109.0H26A—C26—H26C109.5
C12—C11—C10112.14 (12)H26B—C26—H26C109.5
C12—C11—H11109.0C18—C27—H27119.2
C12—C11—C26110.89 (15)C18—C27—C28121.7 (3)
C26—C11—C10106.81 (18)C28—C27—H27119.2
C26—C11—H11109.0C21—C28—C27120.4 (2)
C11—C12—H12A108.0C21—C28—H28119.8
C11—C12—H12B108.0C27—C28—H28119.8
H12A—C12—H12B107.3C17—C29—H29119.3
C13—C12—C11117.11 (13)C30—C29—C17121.35 (16)
C13—C12—H12A108.0C30—C29—H29119.3
C13—C12—H12B108.0C14—C30—H30119.4
O2—C13—C12123.22 (19)C29—C30—C14121.2 (2)
O2—C13—C14119.93 (18)C29—C30—H30119.4
C14—C13—C12116.79 (13)C8—C31—H31119.5
C15—C14—C13119.02 (14)C32—C31—C8121.00 (14)
C30—C14—C13122.92 (18)C32—C31—H31119.5
C30—C14—C15118.0 (2)C5—C32—H32119.1
C14—C15—H15119.8C31—C32—C5121.75 (19)
C16—C15—C14120.47 (15)C31—C32—H32119.1
C16—C15—H15119.8
O2—C13—C14—C152.5 (2)C11—C12—C13—C14176.89 (11)
O2—C13—C14—C30175.47 (15)C12—C13—C14—C15179.79 (13)
O3—C9—C10—C1161.0 (2)C12—C13—C14—C301.8 (2)
O3—C9—C24—O1167.99 (13)C13—C14—C15—C16176.96 (14)
O3—C9—C24—C2511.86 (17)C13—C14—C30—C29176.88 (16)
C1—C2—C3—C41.0 (3)C14—C15—C16—C170.3 (3)
C1—C22—C23—C40.4 (3)C15—C14—C30—C291.1 (3)
C2—C1—C22—C230.8 (3)C15—C16—C17—C18179.41 (15)
C2—C3—C4—C5177.02 (17)C15—C16—C17—C290.4 (3)
C2—C3—C4—C230.5 (3)C16—C17—C18—C191.2 (3)
C3—C4—C5—C60.5 (2)C16—C17—C18—C27179.6 (2)
C3—C4—C5—C32177.54 (15)C16—C17—C29—C300.4 (3)
C3—C4—C23—C220.2 (3)C17—C18—C19—C20180.0 (2)
C4—C5—C6—C7173.26 (14)C17—C18—C27—C28179.9 (3)
C4—C5—C32—C31173.58 (13)C17—C29—C30—C140.3 (3)
C5—C4—C23—C22177.31 (17)C18—C17—C29—C30179.40 (16)
C5—C6—C7—C80.3 (2)C18—C19—C20—C210.8 (5)
C6—C5—C32—C313.6 (2)C18—C27—C28—C210.7 (5)
C6—C7—C8—C9170.52 (13)C19—C18—C27—C281.6 (4)
C6—C7—C8—C314.8 (2)C19—C20—C21—C283.1 (5)
C7—C8—C9—O3178.49 (12)C20—C21—C28—C273.0 (5)
C7—C8—C9—C1054.6 (2)C22—C1—C2—C31.1 (3)
C7—C8—C9—C2462.0 (2)C23—C4—C5—C6176.89 (15)
C7—C8—C31—C325.2 (2)C23—C4—C5—C320.1 (2)
C8—C9—C10—C1166.22 (17)C24—C9—C10—C11175.88 (11)
C8—C9—C24—O171.8 (2)C26—C11—C12—C1362.7 (2)
C8—C9—C24—C25108.3 (2)C27—C18—C19—C201.5 (4)
C8—C31—C32—C51.0 (2)C29—C17—C18—C19178.7 (2)
C9—C8—C31—C32170.23 (13)C29—C17—C18—C270.3 (3)
C9—C10—C11—C1268.05 (17)C30—C14—C15—C161.1 (2)
C9—C10—C11—C26170.27 (12)C31—C8—C9—O36.32 (17)
C10—C9—C24—O149.7 (2)C31—C8—C9—C10120.56 (17)
C10—C9—C24—C25130.17 (19)C31—C8—C9—C24122.8 (2)
C10—C11—C12—C13177.99 (11)C32—C5—C6—C73.9 (2)
C11—C12—C13—O20.3 (2)
 

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