PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2012 June 1; 68(Pt 6): o1877–o1878.
Published online 2012 May 26. doi:  10.1107/S1600536812023124
PMCID: PMC3379440

(2E)-3-(4-Cyano­phen­yl)-1-(4,4′′-difluoro-5′-meth­oxy-1,1′:3′,1′′-terphenyl-4′-yl)prop-2-en-1-one

Abstract

In the title compound, C29H19F2NO2, the central benzene ring forms a dihedral angle of 56.92 (12)° with the cyano­benzene ring and dihedral angles of 40.91 (12) and 44.76 (12)° with the two fluoro­benzene rings. In the crystal, C—H(...)O and C—H(...)F hydrogen bonds link the mol­ecules into sheets lying parallel to the ab plane. The crystal packing also features C—H(...)π inter­actions involving the central benzene ring.

Related literature  

For background to terphenyls, see: Fun, Hemamalini et al. (2011 [triangle]); Fun, Shahani et al. (2011 [triangle]); Fun et al. (2012 [triangle]); Betz et al. (2011 [triangle]). For a related structure, see: Fun, Chia et al. (2011 [triangle]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-68-o1877-scheme1.jpg

Experimental  

Crystal data  

  • C29H19F2NO2
  • M r = 451.45
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-68-o1877-efi1.jpg
  • a = 6.9656 (2) Å
  • b = 11.2404 (3) Å
  • c = 14.6014 (3) Å
  • α = 96.108 (1)°
  • β = 90.415 (1)°
  • γ = 104.764 (1)°
  • V = 1098.51 (5) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 100 K
  • 0.34 × 0.20 × 0.12 mm

Data collection  

  • Bruker APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.968, T max = 0.989
  • 17054 measured reflections
  • 3828 independent reflections
  • 2982 reflections with I > 2σ(I)
  • R int = 0.036

Refinement  

  • R[F 2 > 2σ(F 2)] = 0.050
  • wR(F 2) = 0.112
  • S = 1.03
  • 3828 reflections
  • 308 parameters
  • H-atom parameters constrained
  • Δρmax = 0.31 e Å−3
  • Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812023124/hb6802sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023124/hb6802Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812023124/hb6802Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

HKF and WSL thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). WSL also thanks the Malaysian Government and USM for the award of the post of Research Officer under the Research University Grant (1001/PFIZIK/811160). BN thanks the UGC for financial assistance through the SAP and BSR one-time grant for the purchase of chemicals. SS thanks Mangalore University for the research facilities.

supplementary crystallographic information

Comment

In continuation of our work on synthesis of terphenyl chalcones (Fun, Hemamalini et al., 2011; Fun, Shahani et al., 2011; Betz et al., 2011), the title compound is prepared and its crystal structure is reported. The starting material of the title compound was prepared from 4,4'-difluoro chalcone by several steps (Fun et al., 2012).

In the title compound (Fig. 1), the central benzene ring (C13–C18) forms dihedral angles of 56.92 (12)° with the cyanobenzene ring (C22–C28/N1) and 40.91 (12) and 44.76 (12)°, respectively, with the fluorobenzene rings (C1–C6/F1 & C7–C12/F2). Bond lengths are angles are within the normal ranges and are comparable with the related structure (Fun, Chia et al., 2011).

In the crystal packing (Fig. 2), intermolecular C7—H7A···O1 and C29—H29A···F2 hydrogen bonds (Table 1) link the molecules to form planes parallel to the ab plane. The crystal packing is further stabilized by C—H···π interactions (Table 1), involving the central benzene ring.

Experimental

To a mixture of 1-(4,4''-difluoro-5'-methoxy-1,1':3',1''-terphenyl-4'-yl) ethanone (0.338 g, 0.001 mol) and 4-cyanobenzaldehyde (0.131 g, 0.001 mol) in 30 ml e thanol, 0.5 ml of 10% sodium hydroxide solution was added and stirred at 5–10°C for 3 h. The precipitate formed was collected by filtration and purified by recrystallization from ethanol. Colourless plates were grown from acetone solution by slow evaporation method and yield of the compound was 78%. M.p.: 450 K.

Refinement

All the H atoms were positioned geometrically and were refined with a riding model with Uiso(H) = 1.2 or 1.5 Ueq(C) [C–H = 0.95 or 0.98 Å]. A rotating group model was applied to the methyl group. In the final refinement, nine outliners were omitted, -6 10 5, 0 0 1, -6 1 0, -5 10 7, -5 11 5, -2 11 8, -6 2 0, -4 9 10 and -2 9 11.

Figures

Fig. 1.
The molecular structure of the title compound, showing 50% probability displacement ellipsoids.
Fig. 2.
The crystal packing of the title compound, viewed along the a axis, showing the plane parallel to the ab plane. H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.

Crystal data

C29H19F2NO2Z = 2
Mr = 451.45F(000) = 468
Triclinic, P1Dx = 1.365 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.9656 (2) ÅCell parameters from 6297 reflections
b = 11.2404 (3) Åθ = 2.2–30.1°
c = 14.6014 (3) ŵ = 0.10 mm1
α = 96.108 (1)°T = 100 K
β = 90.415 (1)°Plate, colourless
γ = 104.764 (1)°0.34 × 0.20 × 0.12 mm
V = 1098.51 (5) Å3

Data collection

Bruker APEXII CCD diffractometer3828 independent reflections
Radiation source: fine-focus sealed tube2982 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
[var phi] and ω scansθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −8→8
Tmin = 0.968, Tmax = 0.989k = −13→13
17054 measured reflectionsl = −17→17

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0128P)2 + 2.0889P] where P = (Fo2 + 2Fc2)/3
3828 reflections(Δ/σ)max < 0.001
308 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = −0.23 e Å3

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
F1−0.3094 (2)1.07639 (17)0.96874 (12)0.0383 (5)
F20.1740 (2)0.29331 (13)0.46224 (11)0.0282 (4)
O10.2862 (3)1.22148 (17)0.70626 (13)0.0252 (4)
O20.6812 (3)1.09304 (16)0.60777 (12)0.0209 (4)
N11.5517 (4)1.7077 (3)0.98443 (19)0.0430 (7)
C1−0.1786 (4)1.0421 (3)0.90947 (19)0.0256 (6)
C20.0215 (4)1.0968 (3)0.92571 (19)0.0235 (6)
H2A0.06681.15600.97780.028*
C30.1545 (4)1.0639 (2)0.86487 (18)0.0204 (6)
H3A0.29271.10030.87580.025*
C40.0899 (4)0.9781 (2)0.78753 (17)0.0181 (6)
C5−0.1138 (4)0.9222 (3)0.77510 (18)0.0216 (6)
H5A−0.16030.86180.72390.026*
C6−0.2491 (4)0.9536 (3)0.83625 (19)0.0251 (6)
H6A−0.38710.91480.82780.030*
C70.2004 (4)0.4356 (2)0.59530 (19)0.0225 (6)
H7A0.16180.36930.63220.027*
C80.2424 (4)0.5575 (2)0.63458 (18)0.0204 (6)
H8A0.23130.57490.69920.025*
C90.3007 (4)0.6554 (2)0.58073 (18)0.0185 (6)
C100.3164 (4)0.6277 (2)0.48615 (18)0.0205 (6)
H10A0.35770.69310.44870.025*
C110.2725 (4)0.5059 (2)0.44581 (18)0.0210 (6)
H11A0.28130.48720.38120.025*
C120.2160 (4)0.4130 (2)0.50176 (19)0.0206 (6)
C130.2098 (4)0.8217 (2)0.68521 (17)0.0183 (6)
H13A0.10300.76000.70520.022*
C140.2329 (4)0.9455 (2)0.72000 (17)0.0179 (6)
C150.3935 (4)1.0359 (2)0.69134 (17)0.0181 (6)
C160.5288 (4)0.9990 (2)0.63103 (17)0.0181 (6)
C170.5009 (4)0.8762 (2)0.59581 (17)0.0182 (6)
H17A0.59190.85310.55370.022*
C180.3390 (4)0.7864 (2)0.62211 (17)0.0188 (6)
C190.4204 (4)1.1726 (2)0.71882 (17)0.0198 (6)
C200.6148 (4)1.2424 (2)0.76212 (17)0.0214 (6)
H20A0.70791.19770.77640.026*
C210.6651 (4)1.3647 (2)0.78190 (18)0.0216 (6)
H21A0.56991.40770.76720.026*
C220.8547 (4)1.4389 (2)0.82446 (18)0.0216 (6)
C230.8852 (4)1.5658 (3)0.84806 (19)0.0274 (7)
H23A0.78251.60400.83540.033*
C241.0628 (4)1.6374 (3)0.8896 (2)0.0292 (7)
H24A1.08141.72390.90540.035*
C251.2137 (4)1.5813 (3)0.90810 (18)0.0269 (7)
C261.1865 (4)1.4552 (3)0.8842 (2)0.0295 (7)
H26A1.28911.41700.89710.035*
C271.0109 (4)1.3854 (3)0.8418 (2)0.0282 (7)
H27A0.99501.29960.82390.034*
C281.4004 (5)1.6533 (3)0.9511 (2)0.0325 (7)
C290.8394 (4)1.0612 (3)0.55730 (19)0.0234 (6)
H29A0.94431.13640.55100.035*
H29B0.78891.02050.49600.035*
H29C0.89361.00480.59030.035*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
F10.0321 (10)0.0470 (12)0.0418 (11)0.0210 (9)0.0180 (8)0.0045 (9)
F20.0287 (9)0.0151 (9)0.0386 (10)0.0049 (7)0.0016 (7)−0.0046 (7)
O10.0235 (10)0.0234 (11)0.0322 (11)0.0118 (9)0.0014 (8)0.0047 (9)
O20.0191 (9)0.0167 (10)0.0261 (10)0.0039 (8)0.0083 (8)−0.0002 (8)
N10.0341 (16)0.0406 (17)0.0495 (17)0.0063 (13)−0.0063 (13)−0.0082 (14)
C10.0269 (15)0.0285 (17)0.0281 (16)0.0161 (13)0.0122 (12)0.0100 (13)
C20.0282 (15)0.0214 (15)0.0230 (14)0.0103 (12)0.0066 (12)0.0019 (12)
C30.0202 (14)0.0192 (15)0.0232 (14)0.0065 (11)0.0020 (11)0.0044 (11)
C40.0190 (13)0.0175 (14)0.0204 (14)0.0079 (11)0.0023 (11)0.0059 (11)
C50.0200 (14)0.0239 (16)0.0230 (14)0.0078 (12)−0.0001 (11)0.0061 (12)
C60.0168 (14)0.0296 (17)0.0334 (16)0.0106 (12)0.0042 (12)0.0124 (13)
C70.0206 (14)0.0173 (15)0.0319 (16)0.0076 (11)0.0036 (12)0.0056 (12)
C80.0197 (14)0.0224 (15)0.0199 (14)0.0067 (12)0.0025 (11)0.0020 (11)
C90.0124 (12)0.0184 (15)0.0241 (14)0.0032 (11)−0.0006 (10)0.0014 (11)
C100.0186 (13)0.0183 (15)0.0246 (14)0.0047 (11)0.0007 (11)0.0028 (12)
C110.0178 (14)0.0231 (15)0.0218 (14)0.0069 (11)0.0019 (11)−0.0025 (12)
C120.0142 (13)0.0150 (14)0.0316 (16)0.0045 (11)0.0000 (11)−0.0036 (12)
C130.0160 (13)0.0183 (15)0.0195 (13)0.0023 (11)0.0000 (11)0.0030 (11)
C140.0155 (13)0.0217 (15)0.0169 (13)0.0057 (11)−0.0032 (10)0.0025 (11)
C150.0174 (13)0.0193 (15)0.0175 (13)0.0043 (11)−0.0025 (11)0.0023 (11)
C160.0149 (13)0.0209 (15)0.0184 (13)0.0039 (11)−0.0013 (11)0.0031 (11)
C170.0171 (13)0.0205 (15)0.0175 (13)0.0064 (11)0.0008 (10)0.0003 (11)
C180.0189 (13)0.0193 (15)0.0188 (13)0.0060 (11)−0.0029 (11)0.0034 (11)
C190.0243 (14)0.0209 (15)0.0161 (13)0.0087 (12)0.0051 (11)0.0027 (11)
C200.0257 (15)0.0197 (16)0.0204 (14)0.0096 (12)0.0013 (11)−0.0004 (11)
C210.0245 (14)0.0210 (16)0.0214 (14)0.0108 (12)0.0062 (11)−0.0005 (12)
C220.0278 (15)0.0187 (15)0.0187 (14)0.0085 (12)0.0067 (11)−0.0024 (11)
C230.0279 (16)0.0258 (17)0.0288 (16)0.0097 (13)0.0046 (12)−0.0029 (13)
C240.0333 (17)0.0211 (16)0.0304 (16)0.0072 (13)0.0086 (13)−0.0097 (13)
C250.0271 (15)0.0295 (17)0.0204 (14)0.0034 (13)0.0034 (12)−0.0039 (12)
C260.0292 (16)0.0287 (17)0.0312 (16)0.0088 (13)0.0007 (13)0.0024 (13)
C270.0312 (16)0.0199 (15)0.0326 (16)0.0057 (13)−0.0002 (13)0.0016 (13)
C280.0315 (17)0.0304 (18)0.0329 (17)0.0068 (14)0.0027 (14)−0.0051 (14)
C290.0192 (14)0.0241 (16)0.0265 (15)0.0047 (12)0.0046 (11)0.0026 (12)

Geometric parameters (Å, º)

F1—C11.360 (3)C13—C181.390 (4)
F2—C121.364 (3)C13—C141.398 (4)
O1—C191.221 (3)C13—H13A0.9500
O2—C161.367 (3)C14—C151.406 (4)
O2—C291.429 (3)C15—C161.403 (4)
N1—C281.150 (4)C15—C191.510 (4)
C1—C61.375 (4)C16—C171.385 (4)
C1—C21.380 (4)C17—C181.394 (4)
C2—C31.379 (4)C17—H17A0.9500
C2—H2A0.9500C19—C201.479 (4)
C3—C41.396 (4)C20—C211.328 (4)
C3—H3A0.9500C20—H20A0.9500
C4—C51.400 (4)C21—C221.464 (4)
C4—C141.490 (4)C21—H21A0.9500
C5—C61.387 (4)C22—C231.392 (4)
C5—H5A0.9500C22—C271.404 (4)
C6—H6A0.9500C23—C241.387 (4)
C7—C121.373 (4)C23—H23A0.9500
C7—C81.385 (4)C24—C251.395 (4)
C7—H7A0.9500C24—H24A0.9500
C8—C91.398 (4)C25—C261.387 (4)
C8—H8A0.9500C25—C281.443 (4)
C9—C101.394 (4)C26—C271.376 (4)
C9—C181.488 (4)C26—H26A0.9500
C10—C111.388 (4)C27—H27A0.9500
C10—H10A0.9500C29—H29A0.9800
C11—C121.374 (4)C29—H29B0.9800
C11—H11A0.9500C29—H29C0.9800
C16—O2—C29118.1 (2)C14—C15—C19122.5 (2)
F1—C1—C6119.2 (2)O2—C16—C17123.8 (2)
F1—C1—C2118.5 (3)O2—C16—C15115.1 (2)
C6—C1—C2122.3 (3)C17—C16—C15121.1 (2)
C3—C2—C1118.7 (3)C16—C17—C18120.0 (2)
C3—C2—H2A120.7C16—C17—H17A120.0
C1—C2—H2A120.7C18—C17—H17A120.0
C2—C3—C4121.2 (2)C13—C18—C17119.1 (2)
C2—C3—H3A119.4C13—C18—C9120.3 (2)
C4—C3—H3A119.4C17—C18—C9120.5 (2)
C3—C4—C5118.2 (2)O1—C19—C20122.5 (2)
C3—C4—C14121.3 (2)O1—C19—C15120.8 (2)
C5—C4—C14120.5 (2)C20—C19—C15116.7 (2)
C6—C5—C4121.2 (3)C21—C20—C19123.0 (3)
C6—C5—H5A119.4C21—C20—H20A118.5
C4—C5—H5A119.4C19—C20—H20A118.5
C1—C6—C5118.4 (3)C20—C21—C22125.6 (3)
C1—C6—H6A120.8C20—C21—H21A117.2
C5—C6—H6A120.8C22—C21—H21A117.2
C12—C7—C8118.3 (3)C23—C22—C27118.2 (3)
C12—C7—H7A120.9C23—C22—C21120.4 (2)
C8—C7—H7A120.9C27—C22—C21121.5 (2)
C7—C8—C9121.1 (2)C24—C23—C22121.3 (3)
C7—C8—H8A119.5C24—C23—H23A119.4
C9—C8—H8A119.5C22—C23—H23A119.4
C10—C9—C8118.5 (2)C23—C24—C25119.4 (3)
C10—C9—C18120.2 (2)C23—C24—H24A120.3
C8—C9—C18121.2 (2)C25—C24—H24A120.3
C11—C10—C9121.0 (3)C26—C25—C24120.1 (3)
C11—C10—H10A119.5C26—C25—C28119.2 (3)
C9—C10—H10A119.5C24—C25—C28120.8 (3)
C12—C11—C10118.3 (2)C27—C26—C25120.0 (3)
C12—C11—H11A120.9C27—C26—H26A120.0
C10—C11—H11A120.9C25—C26—H26A120.0
F2—C12—C7118.8 (2)C26—C27—C22121.0 (3)
F2—C12—C11118.3 (2)C26—C27—H27A119.5
C7—C12—C11122.9 (2)C22—C27—H27A119.5
C18—C13—C14121.7 (2)N1—C28—C25177.9 (3)
C18—C13—H13A119.1O2—C29—H29A109.5
C14—C13—H13A119.1O2—C29—H29B109.5
C13—C14—C15118.8 (2)H29A—C29—H29B109.5
C13—C14—C4119.5 (2)O2—C29—H29C109.5
C15—C14—C4121.7 (2)H29A—C29—H29C109.5
C16—C15—C14119.2 (2)H29B—C29—H29C109.5
C16—C15—C19118.3 (2)
F1—C1—C2—C3−178.9 (2)C19—C15—C16—O24.0 (3)
C6—C1—C2—C31.8 (4)C14—C15—C16—C173.3 (4)
C1—C2—C3—C40.7 (4)C19—C15—C16—C17−173.4 (2)
C2—C3—C4—C5−2.5 (4)O2—C16—C17—C18−178.8 (2)
C2—C3—C4—C14177.9 (2)C15—C16—C17—C18−1.7 (4)
C3—C4—C5—C61.8 (4)C14—C13—C18—C172.8 (4)
C14—C4—C5—C6−178.6 (2)C14—C13—C18—C9−175.0 (2)
F1—C1—C6—C5178.3 (2)C16—C17—C18—C13−1.3 (4)
C2—C1—C6—C5−2.5 (4)C16—C17—C18—C9176.5 (2)
C4—C5—C6—C10.6 (4)C10—C9—C18—C13134.0 (3)
C12—C7—C8—C9−0.5 (4)C8—C9—C18—C13−43.9 (4)
C7—C8—C9—C10−0.1 (4)C10—C9—C18—C17−43.7 (3)
C7—C8—C9—C18177.8 (2)C8—C9—C18—C17138.3 (3)
C8—C9—C10—C110.9 (4)C16—C15—C19—O1124.0 (3)
C18—C9—C10—C11−177.1 (2)C14—C15—C19—O1−52.6 (4)
C9—C10—C11—C12−1.0 (4)C16—C15—C19—C20−56.7 (3)
C8—C7—C12—F2−179.7 (2)C14—C15—C19—C20126.7 (3)
C8—C7—C12—C110.5 (4)O1—C19—C20—C21−7.0 (4)
C10—C11—C12—F2−179.6 (2)C15—C19—C20—C21173.7 (2)
C10—C11—C12—C70.3 (4)C19—C20—C21—C22−179.9 (2)
C18—C13—C14—C15−1.2 (4)C20—C21—C22—C23−175.3 (3)
C18—C13—C14—C4180.0 (2)C20—C21—C22—C275.3 (4)
C3—C4—C14—C13137.4 (3)C27—C22—C23—C24−1.6 (4)
C5—C4—C14—C13−42.2 (3)C21—C22—C23—C24179.1 (3)
C3—C4—C14—C15−41.4 (4)C22—C23—C24—C250.0 (4)
C5—C4—C14—C15139.0 (3)C23—C24—C25—C260.6 (4)
C13—C14—C15—C16−1.9 (4)C23—C24—C25—C28179.8 (3)
C4—C14—C15—C16176.9 (2)C24—C25—C26—C270.4 (4)
C13—C14—C15—C19174.7 (2)C28—C25—C26—C27−178.9 (3)
C4—C14—C15—C19−6.5 (4)C25—C26—C27—C22−2.0 (4)
C29—O2—C16—C17−11.4 (3)C23—C22—C27—C262.5 (4)
C29—O2—C16—C15171.4 (2)C21—C22—C27—C26−178.1 (3)
C14—C15—C16—O2−179.3 (2)

Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of the C13–C18 ring.

D—H···AD—HH···AD···AD—H···A
C7—H7A···O1i0.952.403.213 (3)143
C29—H29A···F2ii0.982.543.447 (3)155
C29—H29B···Cg1iii0.982.753.521 (3)136

Symmetry codes: (i) x, y−1, z; (ii) x+1, y+1, z; (iii) −x+1, −y+2, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6802).

References

  • Betz, R., Gerber, T., Hosten, E., Samshuddin, S., Narayana, B. & Yathirajan, H. S. (2011). Acta Cryst. E67, o3159–o3160. [PMC free article] [PubMed]
  • Bruker (2009). APEX2, SAINT and SADABSBruker AXS Inc., Madison, Wisconsin, USA.
  • Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107.
  • Fun, H.-K., Chia, T. S., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2011). Acta Cryst. E67, o3390. [PMC free article] [PubMed]
  • Fun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2011). Acta Cryst. E67, o3327–o3328. [PMC free article] [PubMed]
  • Fun, H.-K., Hemamalini, M., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2012). Acta Cryst. E68, o163. [PMC free article] [PubMed]
  • Fun, H.-K., Shahani, T., Samshuddin, S., Narayana, B. & Sarojini, B. K. (2011). Acta Cryst. E67, o3514. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography