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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 12| December 2011| Page o3209
https://doi.org/10.1107/S160053681104493X

Dibenzo[a,e]penta­cyclo­[12.2.1.16,9.02,13.05.10]octa­deca-2(13),5(10)-diene

Dixie Gautreaux,a Tamara R. Schaller Nauman,a Frank R. Fronczeka* and Steven F. Watkinsa

aDepartment of Chemistry, Louisiana State University, Baton Rouge, LA 70803-1804, USA
*Correspondence e-mail: ffroncz@lsu.edu

(Received 11 October 2011; accepted 26 October 2011; online 5 November 2011)

In the title compound, C26H24, the central cyclo­octa­tetra­ene ring has a boat conformation, and the mol­ecule is saddle shaped. The seat is defined by the mean plane of the four-atom attachment points (r.m.s. deviation = 0.014 Å) of the two bicyclo­heptane substituents. These substituents comprise the pommel and cantle, with each mean plane defined by four atoms proximate to the seat (r.m.s. deviations = 0.001 and 0.000 Å). Relative to the seat, the pommel and cantle bend up 33.36 (5) and 34.22 (4)°, while the benzo units (flaps, r.m.s. deviations = 0.008 and 0.013 Å) bend down 33.48 (4) and 36.58 (4)°.

Related literature

For related structures, see: Cambridge Structural Database(Allen, 2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]) reference codes BUPDOF and BUPDUL (Durr et al., 1983[Durr, H., Klauck, G., Peters, K. & von Schnering, H. G. (1983). Angew. Chem. Int. Ed. 22, 332.]) and RIBCAH (Sygula et al., 2007[Sygula, A., Fronczek, F. R., Sygula, R., Rabideau, P. W. & Olmstead, M. M. (2007). J. Am. Chem. Soc. 129, 3842-3843.]). For the synthesis of the title compound, see: Schaller (1994[Schaller, T. R. (1994). PhD dissertation, Louisiana State University, Baton Rouge, USA.]).

[Scheme 1]

Experimental

Crystal data

  • C26H24

  • Mr = 336.45

  • Triclinic, [P \overline 1]

  • a = 9.6962 (4) Å

  • b = 9.7754 (4) Å

  • c = 10.3676 (4) Å

  • α = 77.896 (2)°

  • β = 63.781 (2)°

  • γ = 85.497 (2)°

  • V = 861.87 (6) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 90 K

  • 0.48 × 0.48 × 0.22 mm
Data collection

  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) Tmin = 0.966, Tmax = 0.984

  • 8966 measured reflections

  • 5019 independent reflections

  • 4347 reflections with I > 2σ(I)

  • Rint = 0.024
Refinement

  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.121

  • S = 1.05

  • 5019 reflections

  • 236 parameters

  • H-atom parameters constrained

  • Δρmax = 0.41 e Å−3

  • Δρmin = −0.25 e Å−3

Data collection: COLLECT (Nonius, 2000[Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and SCALEPACK; program(s) used to solve structure: SHELXS86 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053681104493X/mw2032sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681104493X/mw2032Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S160053681104493X/mw2032Isup3.cdx

checkCIF report


Comment top

The central 8-ring of the title compound adopts the boat configuration, and the overall shape of the molecule is that of a saddle. Relative to the mean plane of the saddle seat (C07, C08, C15, C16, δr.m.s. = 0.014 Å), the two bicycloheptane moieties (mean planes C07, C08, C22, C24, δr.m.s. = 0.001 Å, and C15, C16, C17, C19, δr.m.s. = 0.000 Å) bend up 33.36 (5)° and 34.22 (4)°, while the mean planes of the benzo moieties (C01 – C06, δr.m.s. = 0.008. and C09 – C14, δr.m.s. = 0.013 Å) bend down 33.48 (4)° and 36.58 (4)°.

Related literature top

For related structures, see: Cambridge Structural Database(Allen, 2002) reference codes BUPDOF and BUPDUL (Durr et al., 1983) and RIBCAH (Sygula et al., 2007). For the synthesis of the title compound, see: Schaller (1994).

Experimental top

The preparation is described by Schaller (1994). Suitable crystals were obtained by recrystallization from benzene.

Refinement top

All H atoms were placed in calculated positions, guided by difference maps, with C—H bond distances 0.95 (aromatic C) and 0.99 (alkyl C) Å, and Uiso=1.2Ueq, thereafter refined as riding.

Structure description top

The central 8-ring of the title compound adopts the boat configuration, and the overall shape of the molecule is that of a saddle. Relative to the mean plane of the saddle seat (C07, C08, C15, C16, δr.m.s. = 0.014 Å), the two bicycloheptane moieties (mean planes C07, C08, C22, C24, δr.m.s. = 0.001 Å, and C15, C16, C17, C19, δr.m.s. = 0.000 Å) bend up 33.36 (5)° and 34.22 (4)°, while the mean planes of the benzo moieties (C01 – C06, δr.m.s. = 0.008. and C09 – C14, δr.m.s. = 0.013 Å) bend down 33.48 (4)° and 36.58 (4)°.

For related structures, see: Cambridge Structural Database(Allen, 2002) reference codes BUPDOF and BUPDUL (Durr et al., 1983) and RIBCAH (Sygula et al., 2007). For the synthesis of the title compound, see: Schaller (1994).

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. View of (I) (50% probability displacement ellipsoids)
Dibenzo[a,e]pentacyclo[12.2.1.16,9.02,13.05.10]octadeca- 2(13),5(10)-diene top
Crystal data top
C26H24Z = 2
Mr = 336.45F(000) = 360
Triclinic, P1Dx = 1.296 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.6962 (4) ÅCell parameters from 4596 reflections
b = 9.7754 (4) Åθ = 2.6–30.0°
c = 10.3676 (4) ŵ = 0.07 mm−1
α = 77.896 (2)°T = 90 K
β = 63.781 (2)°Prism, colorless
γ = 85.497 (2)°0.48 × 0.48 × 0.22 mm
V = 861.87 (6) Å3
Data collection top
Nonius KappaCCD
diffractometer		5019 independent reflections
Radiation source: sealed tube4347 reflections with I > 2σ(I)
Horizonally mounted graphite crystal monochromatorRint = 0.024
Detector resolution: 9 pixels mm-1θmax = 30.0°, θmin = 2.8°
CCD rotation images, thick slices scansh = −13→13
Absorption correction: multi-scan
(SCALEPACK; Otwinowski & Minor, 1997)		k = −13→13
Tmin = 0.966, Tmax = 0.984l = −14→14
8966 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.121 w = 1/[σ2(Fo2) + (0.0535P)2 + 0.4358P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.001
5019 reflectionsΔρmax = 0.41 e Å−3
236 parametersΔρmin = −0.25 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraintsExtinction coefficient: 0.015 (4)
Primary atom site location: structure-invariant direct methods
Crystal data top
C26H24γ = 85.497 (2)°
Mr = 336.45V = 861.87 (6) Å3
Triclinic, P1Z = 2
a = 9.6962 (4) ÅMo Kα radiation
b = 9.7754 (4) ŵ = 0.07 mm−1
c = 10.3676 (4) ÅT = 90 K
α = 77.896 (2)°0.48 × 0.48 × 0.22 mm
β = 63.781 (2)°
Data collection top
Nonius KappaCCD
diffractometer		5019 independent reflections
Absorption correction: multi-scan
(SCALEPACK; Otwinowski & Minor, 1997)		4347 reflections with I > 2σ(I)
Tmin = 0.966, Tmax = 0.984Rint = 0.024
8966 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.121H-atom parameters constrained
S = 1.05Δρmax = 0.41 e Å−3
5019 reflectionsΔρmin = −0.25 e Å−3
236 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C010.28621 (12)0.39958 (11)−0.15111 (11)0.0134 (2)
C020.25832 (13)0.47525 (12)−0.26849 (12)0.0164 (2)
H020.29060.4377−0.35460.020*
C030.18494 (13)0.60324 (12)−0.26193 (13)0.0182 (2)
H030.16480.6509−0.34150.022*
C040.14123 (13)0.66103 (11)−0.13797 (13)0.0172 (2)
H040.09170.7489−0.13250.021*
C050.17053 (12)0.58930 (11)−0.02231 (12)0.0153 (2)
H050.14240.63020.06110.018*
C060.24068 (12)0.45787 (11)−0.02517 (11)0.01283 (19)
C070.27322 (12)0.39265 (11)0.10023 (11)0.01297 (19)
C080.24073 (12)0.26227 (11)0.18361 (11)0.01301 (19)
C090.16507 (12)0.14103 (11)0.17577 (11)0.0130 (2)
C100.04120 (12)0.07520 (11)0.30452 (12)0.0153 (2)
H100.00770.11170.39140.018*
C11−0.03322 (13)−0.04209 (12)0.30719 (13)0.0175 (2)
H11−0.1194−0.08240.39400.021*
C120.01873 (14)−0.10005 (12)0.18273 (13)0.0187 (2)
H12−0.0311−0.18050.18400.022*
C130.14420 (13)−0.03930 (11)0.05642 (12)0.0169 (2)
H130.1819−0.0814−0.02730.020*
C140.21718 (12)0.08297 (11)0.04893 (12)0.0137 (2)
C150.35046 (12)0.14034 (11)−0.08965 (12)0.0137 (2)
C160.37693 (12)0.27080 (11)−0.17235 (11)0.0134 (2)
C170.51686 (12)0.26307 (11)−0.31741 (12)0.0151 (2)
H170.57250.3538−0.37430.018*
C180.61003 (13)0.15005 (12)−0.26337 (13)0.0171 (2)
H18A0.69670.1150−0.34430.021*
H18B0.64650.1803−0.19820.021*
C190.47281 (12)0.04601 (11)−0.17980 (12)0.0155 (2)
H190.4917−0.0432−0.12260.019*
C200.43547 (14)0.03038 (12)−0.30813 (13)0.0179 (2)
H20A0.5039−0.0380−0.36450.021*
H20B0.32710.0006−0.27110.021*
C210.46571 (14)0.18041 (12)−0.40311 (12)0.0183 (2)
H21A0.37130.2199−0.40960.022*
H21B0.54790.1811−0.50330.022*
C220.27239 (12)0.26323 (11)0.31521 (12)0.0142 (2)
H220.28990.16950.36630.017*
C230.40970 (12)0.36642 (12)0.24377 (12)0.0158 (2)
H23A0.50240.33090.16870.019*
H23B0.43500.39680.31620.019*
C240.32682 (12)0.47954 (11)0.17707 (12)0.0146 (2)
H240.38920.56550.11380.018*
C250.18178 (13)0.50237 (12)0.31881 (12)0.0170 (2)
H25A0.20460.56840.36760.020*
H25B0.09490.53820.29620.020*
C260.14585 (13)0.35287 (12)0.41540 (12)0.0163 (2)
H26A0.04160.32060.43910.020*
H26B0.15450.34950.50770.020*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C010.0133 (4)0.0118 (4)0.0146 (5)0.0001 (3)−0.0060 (4)−0.0017 (4)
C020.0187 (5)0.0156 (5)0.0160 (5)0.0007 (4)−0.0090 (4)−0.0022 (4)
C030.0195 (5)0.0166 (5)0.0198 (5)0.0010 (4)−0.0116 (4)0.0003 (4)
C040.0165 (5)0.0129 (5)0.0225 (5)0.0023 (4)−0.0099 (4)−0.0017 (4)
C050.0150 (5)0.0124 (5)0.0177 (5)0.0012 (4)−0.0065 (4)−0.0030 (4)
C060.0122 (4)0.0114 (4)0.0141 (4)−0.0002 (3)−0.0055 (4)−0.0014 (3)
C070.0125 (4)0.0125 (5)0.0136 (4)0.0016 (3)−0.0053 (4)−0.0034 (4)
C080.0126 (4)0.0134 (5)0.0129 (4)0.0017 (3)−0.0054 (4)−0.0028 (4)
C090.0140 (4)0.0112 (4)0.0145 (5)0.0016 (3)−0.0076 (4)−0.0009 (3)
C100.0165 (5)0.0141 (5)0.0151 (5)0.0005 (4)−0.0075 (4)−0.0008 (4)
C110.0174 (5)0.0149 (5)0.0183 (5)−0.0020 (4)−0.0077 (4)0.0016 (4)
C120.0212 (5)0.0137 (5)0.0222 (5)−0.0026 (4)−0.0111 (4)−0.0006 (4)
C130.0204 (5)0.0136 (5)0.0182 (5)0.0005 (4)−0.0098 (4)−0.0033 (4)
C140.0151 (4)0.0117 (4)0.0153 (5)0.0017 (3)−0.0080 (4)−0.0019 (4)
C150.0145 (4)0.0134 (5)0.0147 (5)0.0020 (4)−0.0073 (4)−0.0046 (4)
C160.0138 (4)0.0142 (5)0.0138 (4)0.0018 (4)−0.0068 (4)−0.0043 (4)
C170.0150 (5)0.0157 (5)0.0141 (5)0.0016 (4)−0.0055 (4)−0.0043 (4)
C180.0144 (5)0.0185 (5)0.0191 (5)0.0034 (4)−0.0071 (4)−0.0063 (4)
C190.0169 (5)0.0138 (5)0.0170 (5)0.0033 (4)−0.0081 (4)−0.0049 (4)
C200.0207 (5)0.0164 (5)0.0191 (5)0.0028 (4)−0.0096 (4)−0.0076 (4)
C210.0221 (5)0.0189 (5)0.0157 (5)0.0018 (4)−0.0089 (4)−0.0057 (4)
C220.0146 (4)0.0142 (5)0.0136 (4)0.0006 (4)−0.0063 (4)−0.0024 (4)
C230.0149 (5)0.0174 (5)0.0159 (5)−0.0007 (4)−0.0074 (4)−0.0027 (4)
C240.0156 (5)0.0136 (5)0.0148 (5)−0.0002 (4)−0.0067 (4)−0.0029 (4)
C250.0191 (5)0.0154 (5)0.0169 (5)0.0019 (4)−0.0075 (4)−0.0057 (4)
C260.0173 (5)0.0169 (5)0.0139 (5)0.0005 (4)−0.0058 (4)−0.0038 (4)
Geometric parameters (Å, º) top
C01—C021.4082 (14)C15—C191.5301 (15)
C01—C061.4099 (15)C16—C171.5287 (15)
C01—C161.4758 (14)C17—C181.5433 (15)
C02—C031.3891 (15)C17—C211.5626 (15)
C02—H020.9500C17—H171.0000
C03—C041.3914 (16)C18—C191.5426 (16)
C03—H030.9500C18—H18A0.9900
C04—C051.3883 (15)C18—H18B0.9900
C04—H040.9500C19—C201.5634 (15)
C05—C061.4054 (14)C19—H191.0000
C05—H050.9500C20—C211.5534 (16)
C06—C071.4763 (14)C20—H20A0.9900
C07—C081.3532 (14)C20—H20B0.9900
C07—C241.5314 (15)C21—H21A0.9900
C08—C091.4762 (14)C21—H21B0.9900
C08—C221.5270 (15)C22—C231.5378 (15)
C09—C101.4082 (15)C22—C261.5617 (15)
C09—C141.4098 (15)C22—H221.0000
C10—C111.3910 (15)C23—C241.5420 (15)
C10—H100.9500C23—H23A0.9900
C11—C121.3883 (17)C23—H23B0.9900
C11—H110.9500C24—C251.5650 (15)
C12—C131.3882 (16)C24—H241.0000
C12—H120.9500C25—C261.5550 (15)
C13—C141.4073 (15)C25—H25A0.9900
C13—H130.9500C25—H25B0.9900
C14—C151.4779 (15)C26—H26A0.9900
C15—C161.3512 (15)C26—H26B0.9900
C02—C01—C06118.50 (10)C19—C18—C1793.53 (8)
C02—C01—C16118.22 (9)C19—C18—H18A113.0
C06—C01—C16122.92 (9)C17—C18—H18A113.0
C03—C02—C01121.88 (10)C19—C18—H18B113.0
C03—C02—H02119.1C17—C18—H18B113.0
C01—C02—H02119.1H18A—C18—H18B110.4
C02—C03—C04119.48 (10)C15—C19—C18100.09 (8)
C02—C03—H03120.3C15—C19—C20107.17 (9)
C04—C03—H03120.3C18—C19—C20100.24 (9)
C05—C04—C03119.47 (10)C15—C19—H19115.7
C05—C04—H04120.3C18—C19—H19115.7
C03—C04—H04120.3C20—C19—H19115.7
C04—C05—C06121.88 (10)C21—C20—C19102.90 (9)
C04—C05—H05119.1C21—C20—H20A111.2
C06—C05—H05119.1C19—C20—H20A111.2
C05—C06—C01118.76 (10)C21—C20—H20B111.2
C05—C06—C07117.87 (9)C19—C20—H20B111.2
C01—C06—C07123.22 (9)H20A—C20—H20B109.1
C08—C07—C06130.51 (10)C20—C21—C17102.78 (9)
C08—C07—C24106.88 (9)C20—C21—H21A111.2
C06—C07—C24121.69 (9)C17—C21—H21A111.2
C07—C08—C09131.06 (10)C20—C21—H21B111.2
C07—C08—C22107.00 (9)C17—C21—H21B111.2
C09—C08—C22121.23 (9)H21A—C21—H21B109.1
C10—C09—C14118.74 (10)C08—C22—C23100.36 (8)
C10—C09—C08117.94 (9)C08—C22—C26107.65 (8)
C14—C09—C08123.18 (9)C23—C22—C26100.28 (9)
C11—C10—C09121.42 (10)C08—C22—H22115.5
C11—C10—H10119.3C23—C22—H22115.5
C09—C10—H10119.3C26—C22—H22115.5
C12—C11—C10119.87 (10)C22—C23—C2493.57 (8)
C12—C11—H11120.1C22—C23—H23A113.0
C10—C11—H11120.1C24—C23—H23A113.0
C13—C12—C11119.37 (10)C22—C23—H23B113.0
C13—C12—H12120.3C24—C23—H23B113.0
C11—C12—H12120.3H23A—C23—H23B110.4
C12—C13—C14121.84 (10)C07—C24—C23100.19 (8)
C12—C13—H13119.1C07—C24—C25106.63 (8)
C14—C13—H13119.1C23—C24—C25100.53 (8)
C13—C14—C09118.66 (10)C07—C24—H24115.8
C13—C14—C15118.30 (10)C23—C24—H24115.8
C09—C14—C15122.96 (9)C25—C24—H24115.8
C16—C15—C14129.94 (10)C26—C25—C24102.79 (8)
C16—C15—C19107.15 (9)C26—C25—H25A111.2
C14—C15—C19122.01 (9)C24—C25—H25A111.2
C15—C16—C01131.40 (10)C26—C25—H25B111.2
C15—C16—C17106.96 (9)C24—C25—H25B111.2
C01—C16—C17121.07 (9)H25A—C25—H25B109.1
C16—C17—C18100.22 (8)C25—C26—C22102.68 (8)
C16—C17—C21107.22 (9)C25—C26—H26A111.2
C18—C17—C21100.36 (9)C22—C26—H26A111.2
C16—C17—H17115.6C25—C26—H26B111.2
C18—C17—H17115.6C22—C26—H26B111.2
C21—C17—H17115.6H26A—C26—H26B109.1
C06—C01—C02—C03−1.34 (16)C14—C15—C16—C17−169.06 (10)
C16—C01—C02—C03−174.67 (10)C19—C15—C16—C170.00 (11)
C01—C02—C03—C041.86 (17)C02—C01—C16—C15−130.46 (12)
C02—C03—C04—C05−0.52 (17)C06—C01—C16—C1556.53 (17)
C03—C04—C05—C06−1.31 (16)C02—C01—C16—C1739.74 (14)
C04—C05—C06—C011.81 (16)C06—C01—C16—C17−133.27 (11)
C04—C05—C06—C07177.38 (10)C15—C16—C17—C18−33.99 (11)
C02—C01—C06—C05−0.48 (15)C01—C16—C17—C18153.68 (9)
C16—C01—C06—C05172.52 (10)C15—C16—C17—C2170.33 (11)
C02—C01—C06—C07−175.80 (10)C01—C16—C17—C21−102.00 (11)
C16—C01—C06—C07−2.80 (16)C16—C17—C18—C1951.33 (9)
C05—C06—C07—C08130.07 (12)C21—C17—C18—C19−58.47 (9)
C01—C06—C07—C08−54.57 (16)C16—C15—C19—C1833.99 (11)
C05—C06—C07—C24−37.51 (14)C14—C15—C19—C18−155.89 (9)
C01—C06—C07—C24137.85 (10)C16—C15—C19—C20−70.13 (11)
C06—C07—C08—C091.38 (19)C14—C15—C19—C2099.99 (11)
C24—C07—C08—C09170.36 (10)C17—C18—C19—C15−51.23 (9)
C06—C07—C08—C22−168.83 (10)C17—C18—C19—C2058.45 (9)
C24—C07—C08—C220.14 (11)C15—C19—C20—C2167.15 (10)
C07—C08—C09—C10−128.15 (12)C18—C19—C20—C21−36.87 (10)
C22—C08—C09—C1040.89 (14)C19—C20—C21—C170.10 (11)
C07—C08—C09—C1456.15 (16)C16—C17—C21—C20−67.52 (10)
C22—C08—C09—C14−134.80 (10)C18—C17—C21—C2036.70 (10)
C14—C09—C10—C11−2.22 (15)C07—C08—C22—C23−34.13 (10)
C08—C09—C10—C11−178.12 (10)C09—C08—C22—C23154.49 (9)
C09—C10—C11—C122.77 (17)C07—C08—C22—C2670.26 (10)
C10—C11—C12—C13−0.42 (17)C09—C08—C22—C26−101.12 (11)
C11—C12—C13—C14−2.45 (17)C08—C22—C23—C2451.37 (9)
C12—C13—C14—C092.95 (16)C26—C22—C23—C24−58.90 (9)
C12—C13—C14—C15179.75 (10)C08—C07—C24—C2333.77 (10)
C10—C09—C14—C13−0.60 (15)C06—C07—C24—C23−156.07 (9)
C08—C09—C14—C13175.07 (10)C08—C07—C24—C25−70.56 (10)
C10—C09—C14—C15−177.24 (10)C06—C07—C24—C2599.60 (11)
C08—C09—C14—C15−1.58 (15)C22—C23—C24—C07−51.19 (9)
C13—C14—C15—C16127.20 (12)C22—C23—C24—C2558.03 (9)
C09—C14—C15—C16−56.14 (16)C07—C24—C25—C2668.46 (10)
C13—C14—C15—C19−40.45 (14)C23—C24—C25—C26−35.62 (10)
C09—C14—C15—C19136.20 (11)C24—C25—C26—C22−1.28 (10)
C14—C15—C16—C012.17 (19)C08—C22—C26—C25−66.56 (10)
C19—C15—C16—C01171.23 (11)C23—C22—C26—C2537.88 (10)

Experimental details

Crystal data
Chemical formulaC26H24
Mr336.45
Crystal system, space groupTriclinic, P1
Temperature (K)90
a, b, c (Å)9.6962 (4), 9.7754 (4), 10.3676 (4)
α, β, γ (°)77.896 (2), 63.781 (2), 85.497 (2)
V (Å3)861.87 (6)
Z2
Radiation typeMo Kα
µ (mm−1)0.07
Crystal size (mm)0.48 × 0.48 × 0.22
Data collection
DiffractometerNonius KappaCCD
Absorption correctionMulti-scan
(SCALEPACK; Otwinowski & Minor, 1997)
Tmin, Tmax0.966, 0.984
No. of measured, independent and
observed [I > 2σ(I)] reflections		8966, 5019, 4347
Rint0.024
(sin θ/λ)max (Å−1)0.704
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.121, 1.05
No. of reflections5019
No. of parameters236
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.41, −0.25

Computer programs: COLLECT (Nonius, 2000), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SHELXS86 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

 

Acknowledgements

The purchase of the diffractometer was made possible by Grant No. LEQSF(1999–2000)-ENH-TR-13, administered by the Louisiana Board of Regents.

References

First citationAllen, F. H. (2002). Acta Cryst. B58, 380–388.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationDurr, H., Klauck, G., Peters, K. & von Schnering, H. G. (1983). Angew. Chem. Int. Ed. 22, 332.  Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
 First citationNonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.  Google Scholar
 First citationOtwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.  Google Scholar
 First citationSchaller, T. R. (1994). PhD dissertation, Louisiana State University, Baton Rouge, USA.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSygula, A., Fronczek, F. R., Sygula, R., Rabideau, P. W. & Olmstead, M. M. (2007). J. Am. Chem. Soc. 129, 3842–3843.  Web of Science CSD CrossRef PubMed CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 67| Part 12| December 2011| Page o3209
https://doi.org/10.1107/S160053681104493X
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