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Acta Crystallogr Sect E Struct Rep Online. 2009 June 1; 65(Pt 6): o1186.
Published online 2009 May 7. doi:  10.1107/S1600536809016341
PMCID: PMC2969816

(±)-Ethyl 6-(6-meth­oxy-2-naphth­yl)-4-(4-methyl­phen­yl)-2-oxocyclo­hex-3-ene-1-carboxyl­ate

Abstract

In the title compound, C27H26O4, the dihedral angle between the naphthalene ring system and the benzene ring is 73.10 (5)°. In the crystal, a weak C—H(...)O inter­action occurs. Two C—H groups of the cyclo­hexene ring are disordered over two sets of sites in a 0.796 (5):0.204 (5) ratio, which corresponds to partial overlap of the two enanti­omeric mol­ecules.

Related literature

For related structures, see: Fischer et al. (2007a [triangle],b [triangle], 2008 [triangle]).

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Object name is e-65-o1186-scheme1.jpg

Experimental

Crystal data

  • C27H26O4
  • M r = 414.48
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1186-efi1.jpg
  • a = 18.8013 (10) Å
  • b = 11.3604 (6) Å
  • c = 10.2356 (6) Å
  • β = 93.430 (2)°
  • V = 2182.3 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 296 K
  • 0.44 × 0.38 × 0.22 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: none
  • 26105 measured reflections
  • 4269 independent reflections
  • 3385 reflections with I > 2σ(I)
  • R int = 0.024

Refinement

  • R[F 2 > 2σ(F 2)] = 0.050
  • wR(F 2) = 0.147
  • S = 1.08
  • 4269 reflections
  • 292 parameters
  • H-atom parameters constrained
  • Δρmax = 0.28 e Å−3
  • Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2006 [triangle]); cell refinement: SAINT (Bruker, 2006 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809016341/dn2449sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809016341/dn2449Isup2.hkl

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

Acknowledgments

ANM thanks the University of Mysore for research facilities.

supplementary crystallographic information

Comment

The crystal structures of (8RS,9SR)-ethyl 4-(3-bromothien-2-yl)- 6-(2-furyl)-2-oxocyclohex-3-ene-1-carboxylate, (7RS,8SR)-ethyl 6-(1,3-benzodioxol-5-yl)-3-(3-bromo-2-thienyl)-2-oxocyclohex-3- ene-1-carboxylate and ethyl 4-(3-bromo-2-thienyl)-2-oxo-6- phenylcyclohex-3-ene-1-carboxylate have been reported (Fischer et al., 2007a,b, 2008). As part of our ongoing studies of cyclohexene carboxylates, we now describe the crystal structure of the title compound, (I) (Fig. 1).

The dihedral angle between the mean planes of the naphthalene (C14–C23) and benzene (C2–C7) rings is 73.10 (5)°. Atom C24 is almost coplanar with its attached benzene ring [displacement = 0.029 (3) Å]. The cyclohexene ring shows a distorted half-chair conformation, with atoms C8, C9, C10 and C13 almost coplanar (r.m.s. deviation = 0.009 Å) and C11 and C12 displaced by 0.209 (4) and -0.549 (4) Å, respectively. C11 and C12 are disordered over two sites in a 0.796 (5):0.204 (5) ratio and the minor disorder components show displacements from C8/C9/C10/C13 in the opposite sense: C11A = -0.72 (1) Å; C12A = 0.21 (1)%A. C11 and C12 are stereogenic centres: in the major disorder component, they have S and R conformations respectively. In the minor component, C11A and C12A have R and S conformations, respectively, thus the disorder corresponds to partial overlap of enantiomeric molecules. However, a fully racemic mixture is generated by crystal symmetry.

In the crystal, a weak C—H···O interaction occurs (Table 1), leading to chains of molecules propagating in [001]. There are no aromatic π···π stacking interactions in the title compound, the shortest intermolecular aromatic ring centroid–centroid separation being greater than 5.3 Å.

Experimental

Ethyl acetoacetate (0.65 g, 5 mmol) and (2E)-3-(6-methoxynaphthalen-2-yl)-1-(4-methylphenyl)prop-2- en-1-one (1.51 g, 5 mmol) were refluxed for 6 hr in 10–15 ml of ethanol in the presence of 0.8 ml of 10% NaOH. The reaction mixture was cooled to room temperature and the reaction mass was filtered and recrystallized using acetonitrile to yield colourless blocks of (I) (m.p. 431–433 K). Analysis: found (calculated): C%, 78.15 (78.24); H%, 6.27 (6.32).

Refinement

Atoms C11 and C12 and their attached H atoms are disordered over two sets of sites in a 0.796 (5):0.204 (5) ratio. All H atoms were placed in idealized locations (C—H = 0.93–0.98 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C). The methyl groups were allowed to rotate, but not to tip, to best fit the electron density.

Figures

Fig. 1.
A view of (I) with displacement ellipsoids for the non-hydrogen atoms drawn at the 30% probability level. Only the major disorder component is shown.

Crystal data

C27H26O4F(000) = 880
Mr = 414.48Dx = 1.262 Mg m3
Monoclinic, P21/cMelting point = 431–433 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 18.8013 (10) ÅCell parameters from 9970 reflections
b = 11.3604 (6) Åθ = 2.3–28.1°
c = 10.2356 (6) ŵ = 0.08 mm1
β = 93.430 (2)°T = 296 K
V = 2182.3 (2) Å3Block, colorless
Z = 40.44 × 0.38 × 0.22 mm

Data collection

Bruker SMART CCD diffractometer3385 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.024
graphiteθmax = 26.0°, θmin = 2.1°
ω scansh = −22→23
26105 measured reflectionsk = −14→13
4269 independent reflectionsl = −12→12

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) = 0.147H-atom parameters constrained
S = 1.08w = 1/[σ2(Fo2) + (0.0575P)2 + 0.796P] where P = (Fo2 + 2Fc2)/3
4269 reflections(Δ/σ)max < 0.001
292 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = −0.23 e Å3

Special details

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*/UeqOcc. (<1)
C10.69533 (14)0.5752 (3)0.0533 (3)0.0902 (8)
H1A0.70170.49460.02840.135*
H1B0.73840.60380.09740.135*
H1C0.68430.6218−0.02340.135*
C20.63501 (10)0.58356 (19)0.1438 (2)0.0620 (5)
C30.62922 (11)0.67605 (18)0.2302 (2)0.0653 (5)
H3A0.66370.73480.23380.078*
C40.57306 (10)0.68315 (16)0.3114 (2)0.0573 (5)
H4A0.57080.74630.36890.069*
C50.51993 (8)0.59785 (14)0.30881 (16)0.0450 (4)
C60.52728 (11)0.50508 (18)0.2236 (2)0.0637 (5)
H6A0.49340.44530.22030.076*
C70.58344 (11)0.4987 (2)0.1430 (2)0.0721 (6)
H7A0.58630.43490.08660.087*
C80.45731 (8)0.60752 (14)0.38914 (15)0.0430 (4)
C90.45342 (9)0.68570 (16)0.48623 (17)0.0514 (4)
H9A0.49330.73160.50810.062*
C100.39042 (10)0.70302 (18)0.55941 (19)0.0612 (5)
C110.33058 (11)0.6119 (2)0.5394 (2)0.0475 (7)0.796 (5)
H11A0.34200.54250.59350.057*0.796 (5)
C120.32392 (11)0.5796 (2)0.3939 (2)0.0434 (6)0.796 (5)
H12A0.31540.65200.34330.052*0.796 (5)
C11A0.3197 (4)0.6664 (8)0.4725 (9)0.044 (2)*0.204 (5)
H11B0.30850.71400.39400.053*0.204 (5)
C12A0.3363 (4)0.5376 (9)0.4490 (10)0.042 (2)*0.204 (5)
H12B0.34540.49230.52980.050*0.204 (5)
C130.39476 (8)0.52783 (14)0.35494 (16)0.0454 (4)
H13A0.40340.45190.39620.054*
H13B0.39090.51570.26100.054*
C140.26209 (9)0.49678 (16)0.3617 (2)0.0568 (5)
C150.24061 (10)0.40353 (19)0.4418 (2)0.0645 (5)
H15A0.26640.38810.52030.077*
C160.18260 (10)0.33559 (18)0.4062 (2)0.0636 (5)
H16A0.16930.27510.46100.076*
C170.14295 (9)0.35618 (16)0.28796 (18)0.0523 (4)
C180.16472 (9)0.44890 (16)0.20758 (18)0.0527 (4)
C190.22422 (10)0.51671 (16)0.24743 (19)0.0562 (5)
H19A0.23810.57740.19360.067*
C200.12407 (12)0.47106 (19)0.0890 (2)0.0675 (5)
H20A0.13720.53220.03510.081*
C210.06648 (12)0.4046 (2)0.0531 (2)0.0719 (6)
H21A0.04090.4200−0.02560.086*
C220.04508 (10)0.3132 (2)0.1328 (2)0.0674 (5)
C230.08194 (10)0.28904 (19)0.2477 (2)0.0640 (5)
H23A0.06710.22810.30040.077*
C24−0.03910 (16)0.1578 (3)0.1573 (4)0.1188 (11)
H24A−0.08410.13110.11910.178*
H24B−0.04460.18180.24610.178*
H24C−0.00500.09500.15600.178*
C250.26128 (11)0.6665 (2)0.5797 (2)0.0677 (6)
C260.17635 (17)0.6450 (3)0.7353 (3)0.1119 (11)
H26A0.18310.65920.82870.134*
H26B0.15900.71720.69390.134*
C270.1251 (2)0.5530 (4)0.7114 (4)0.1364 (13)
H27A0.08320.57010.75690.205*
H27B0.14510.47960.74200.205*
H27C0.11280.54780.61920.205*
O10.38635 (9)0.78077 (15)0.64006 (17)0.0873 (5)
O20.24308 (9)0.61212 (16)0.68399 (18)0.0907 (5)
O30.22736 (11)0.74372 (19)0.52718 (18)0.0983 (6)
O4−0.01487 (9)0.25493 (19)0.08413 (19)0.0963 (6)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0763 (15)0.0981 (18)0.1006 (18)0.0025 (14)0.0432 (14)0.0005 (15)
C20.0528 (11)0.0674 (12)0.0676 (12)0.0075 (9)0.0172 (9)0.0070 (10)
C30.0563 (11)0.0581 (11)0.0832 (14)−0.0086 (9)0.0193 (10)0.0062 (10)
C40.0547 (10)0.0488 (10)0.0697 (12)−0.0025 (8)0.0142 (9)−0.0016 (8)
C50.0416 (8)0.0443 (9)0.0491 (9)0.0030 (7)0.0030 (7)0.0044 (7)
C60.0534 (11)0.0620 (12)0.0772 (13)−0.0077 (9)0.0171 (9)−0.0161 (10)
C70.0635 (12)0.0746 (13)0.0805 (14)−0.0014 (10)0.0222 (10)−0.0232 (11)
C80.0427 (8)0.0407 (8)0.0456 (8)0.0017 (6)0.0019 (6)0.0039 (6)
C90.0461 (9)0.0540 (10)0.0542 (9)−0.0070 (8)0.0033 (7)−0.0056 (8)
C100.0559 (11)0.0678 (12)0.0608 (11)−0.0095 (9)0.0105 (9)−0.0208 (9)
C110.0485 (12)0.0476 (12)0.0471 (13)−0.0005 (9)0.0084 (9)−0.0013 (10)
C120.0438 (11)0.0421 (12)0.0446 (12)−0.0001 (9)0.0059 (9)0.0000 (10)
C130.0474 (9)0.0413 (8)0.0479 (9)−0.0007 (7)0.0072 (7)−0.0018 (7)
C140.0467 (10)0.0538 (10)0.0722 (12)−0.0077 (8)0.0218 (9)−0.0181 (9)
C150.0534 (11)0.0736 (13)0.0653 (12)−0.0040 (9)−0.0049 (9)−0.0039 (10)
C160.0571 (11)0.0631 (12)0.0705 (12)−0.0108 (9)0.0026 (9)0.0089 (10)
C170.0427 (9)0.0522 (10)0.0623 (10)−0.0002 (7)0.0072 (8)−0.0031 (8)
C180.0503 (10)0.0481 (9)0.0610 (10)0.0037 (8)0.0158 (8)−0.0069 (8)
C190.0589 (11)0.0512 (10)0.0606 (11)−0.0048 (8)0.0199 (9)−0.0086 (8)
C200.0771 (14)0.0650 (12)0.0609 (11)0.0125 (11)0.0102 (10)0.0024 (10)
C210.0656 (13)0.0836 (15)0.0655 (12)0.0183 (11)−0.0045 (10)−0.0097 (11)
C220.0470 (10)0.0776 (14)0.0770 (13)0.0034 (10)−0.0006 (9)−0.0139 (11)
C230.0493 (10)0.0646 (12)0.0784 (13)−0.0075 (9)0.0050 (9)0.0018 (10)
C240.0733 (17)0.113 (2)0.168 (3)−0.0341 (17)−0.0115 (19)−0.005 (2)
C250.0553 (12)0.0699 (13)0.0790 (14)−0.0043 (10)0.0145 (10)−0.0293 (12)
C260.103 (2)0.119 (2)0.120 (2)−0.0216 (19)0.0603 (19)−0.0187 (19)
C270.113 (3)0.143 (3)0.156 (3)−0.022 (2)0.040 (2)−0.020 (3)
O10.0792 (10)0.0959 (12)0.0898 (11)−0.0252 (9)0.0284 (8)−0.0513 (9)
O20.0829 (11)0.0923 (12)0.0993 (12)0.0043 (9)0.0245 (10)0.0012 (10)
O30.1126 (14)0.0993 (13)0.0851 (12)0.0236 (12)0.0247 (10)−0.0004 (10)
O40.0593 (9)0.1194 (15)0.1076 (13)−0.0101 (10)−0.0173 (9)−0.0175 (12)

Geometric parameters (Å, °)

C1—C21.510 (3)C13—H13A0.9700
C1—H1A0.9600C13—H13B0.9700
C1—H1B0.9600C14—C191.351 (3)
C1—H1C0.9600C14—C151.413 (3)
C2—C71.367 (3)C15—C161.368 (3)
C2—C31.381 (3)C15—H15A0.9300
C3—C41.385 (3)C16—C171.403 (3)
C3—H3A0.9300C16—H16A0.9300
C4—C51.391 (2)C17—C181.412 (3)
C4—H4A0.9300C17—C231.418 (3)
C5—C61.380 (3)C18—C191.399 (3)
C5—C81.480 (2)C18—C201.417 (3)
C6—C71.380 (3)C19—H19A0.9300
C6—H6A0.9300C20—C211.353 (3)
C7—H7A0.9300C20—H20A0.9300
C8—C91.338 (2)C21—C221.395 (3)
C8—C131.509 (2)C21—H21A0.9300
C9—C101.452 (3)C22—C231.357 (3)
C9—H9A0.9300C22—O41.374 (3)
C10—O11.214 (2)C23—H23A0.9300
C10—C111.533 (3)C24—O41.424 (4)
C10—C11A1.610 (8)C24—H24A0.9600
C11—C251.522 (3)C24—H24B0.9600
C11—C121.531 (3)C24—H24C0.9600
C11—H11A0.9800C25—O31.193 (3)
C12—C141.517 (3)C25—O21.297 (3)
C12—C131.531 (3)C26—C271.432 (4)
C12—H12A0.9800C26—O21.438 (3)
C11A—C12A1.519 (13)C26—H26A0.9700
C11A—C251.599 (8)C26—H26B0.9700
C11A—H11B0.9800C27—H27A0.9600
C12A—C131.508 (9)C27—H27B0.9600
C12A—C141.677 (9)C27—H27C0.9600
C12A—H12B0.9800
C2—C1—H1A109.5C11A—C12A—H12B113.6
C2—C1—H1B109.5C14—C12A—H12B113.7
H1A—C1—H1B109.5H11A—C12A—H12B34.6
C2—C1—H1C109.5C12A—C13—C8113.3 (3)
H1A—C1—H1C109.5C12A—C13—C1229.1 (4)
H1B—C1—H1C109.5C8—C13—C12112.79 (14)
C7—C2—C3117.23 (18)C12A—C13—H13A84.1
C7—C2—C1120.7 (2)C8—C13—H13A109.0
C3—C2—C1122.1 (2)C12—C13—H13A110.7
C2—C3—C4121.37 (18)C12A—C13—H13B129.0
C2—C3—H3A119.3C8—C13—H13B109.1
C4—C3—H3A119.3C12—C13—H13B107.4
C3—C4—C5121.36 (18)H13A—C13—H13B107.8
C3—C4—H4A119.3C19—C14—C15118.27 (17)
C5—C4—H4A119.3C19—C14—C12116.22 (19)
C6—C5—C4116.43 (16)C15—C14—C12125.5 (2)
C6—C5—C8121.39 (15)C19—C14—C12A142.5 (4)
C4—C5—C8122.14 (15)C15—C14—C12A98.9 (4)
C7—C6—C5121.81 (18)C12—C14—C12A27.1 (3)
C7—C6—H6A119.1C16—C15—C14121.29 (19)
C5—C6—H6A119.1C16—C15—H15A119.4
C2—C7—C6121.78 (19)C14—C15—H15A119.4
C2—C7—H7A119.1C15—C16—C17120.66 (19)
C6—C7—H7A119.1C15—C16—H16A119.7
C9—C8—C5122.86 (15)C17—C16—H16A119.7
C9—C8—C13119.62 (15)C16—C17—C18118.01 (17)
C5—C8—C13117.49 (14)C16—C17—C23122.67 (18)
C8—C9—C10123.74 (16)C18—C17—C23119.32 (17)
C8—C9—H9A118.1C19—C18—C17119.70 (17)
C10—C9—H9A118.1C19—C18—C20122.18 (18)
O1—C10—C9122.38 (17)C17—C18—C20118.11 (18)
O1—C10—C11120.41 (17)C14—C19—C18122.06 (18)
C9—C10—C11117.01 (16)C14—C19—H19A119.0
O1—C10—C11A118.7 (3)C18—C19—H19A119.0
C9—C10—C11A110.6 (3)C21—C20—C18121.0 (2)
C11—C10—C11A34.6 (3)C21—C20—H20A119.5
C25—C11—C12109.87 (19)C18—C20—H20A119.5
C25—C11—C10108.75 (17)C20—C21—C22120.7 (2)
C12—C11—C10107.95 (17)C20—C21—H21A119.6
C25—C11—H11A109.7C22—C21—H21A119.6
C12—C11—H11A111.1C23—C22—O4125.6 (2)
C10—C11—H11A109.5C23—C22—C21120.5 (2)
C25—C11—H12B126.6O4—C22—C21113.9 (2)
C12—C11—H12B72.7C22—C23—C17120.4 (2)
C10—C11—H12B121.3C22—C23—H23A119.8
H11A—C11—H12B38.4C17—C23—H23A119.8
C14—C12—C13111.87 (15)O4—C24—H24A109.5
C14—C12—C11112.17 (18)O4—C24—H24B109.5
C13—C12—C11108.90 (19)H24A—C24—H24B109.5
C14—C12—H12A107.8O4—C24—H24C109.5
C13—C12—H12A107.6H24A—C24—H24C109.5
C11—C12—H12A108.3H24B—C24—H24C109.5
C14—C12—H11B118.0O3—C25—O2124.1 (2)
C13—C12—H11B122.9O3—C25—C11128.3 (2)
C11—C12—H11B76.6O2—C25—C11107.5 (2)
H12A—C12—H11B31.9O3—C25—C11A93.5 (4)
C12A—C11A—C25105.4 (7)O2—C25—C11A142.3 (4)
C12A—C11A—C1099.5 (6)C11—C25—C11A34.8 (3)
C25—C11A—C10101.5 (5)C27—C26—O2109.9 (3)
C12A—C11A—H12A74.0C27—C26—H26A109.7
C25—C11A—H12A132.8O2—C26—H26A109.7
C10—C11A—H12A125.5C27—C26—H26B109.7
C12A—C11A—H11B116.0O2—C26—H26B109.7
C25—C11A—H11B116.1H26A—C26—H26B108.2
C10—C11A—H11B116.1C26—C27—H27A109.5
H12A—C11A—H11B41.9C26—C27—H27B109.5
C13—C12A—C11A109.6 (7)H27A—C27—H27B109.5
C13—C12A—C14104.7 (5)C26—C27—H27C109.5
C11A—C12A—C14100.3 (7)H27A—C27—H27C109.5
C13—C12A—H11A129.1H27B—C27—H27C109.5
C11A—C12A—H11A79.0C25—O2—C26117.1 (2)
C14—C12A—H11A123.5C22—O4—C24117.6 (2)
C13—C12A—H12B113.7
C7—C2—C3—C4−0.7 (3)C13—C12—C14—C1584.7 (2)
C1—C2—C3—C4179.2 (2)C11—C12—C14—C15−38.0 (3)
C2—C3—C4—C5−0.4 (3)C13—C12—C14—C12A71.7 (7)
C3—C4—C5—C61.5 (3)C11—C12—C14—C12A−51.0 (6)
C3—C4—C5—C8−176.30 (17)C13—C12A—C14—C19−50.3 (9)
C4—C5—C6—C7−1.4 (3)C11A—C12A—C14—C1963.3 (8)
C8—C5—C6—C7176.36 (19)C13—C12A—C14—C15123.0 (5)
C3—C2—C7—C60.8 (3)C11A—C12A—C14—C15−123.4 (6)
C1—C2—C7—C6−179.1 (2)C13—C12A—C14—C12−67.6 (7)
C5—C6—C7—C20.3 (4)C11A—C12A—C14—C1246.0 (7)
C6—C5—C8—C9169.74 (18)C19—C14—C15—C16−0.7 (3)
C4—C5—C8—C9−12.6 (3)C12—C14—C15—C16177.92 (19)
C6—C5—C8—C13−12.5 (2)C12A—C14—C15—C16−176.1 (3)
C4—C5—C8—C13165.13 (16)C14—C15—C16—C170.5 (3)
C5—C8—C9—C10174.96 (17)C15—C16—C17—C18−0.1 (3)
C13—C8—C9—C10−2.7 (3)C15—C16—C17—C23−179.20 (19)
C8—C9—C10—O1−174.1 (2)C16—C17—C18—C19−0.1 (3)
C8—C9—C10—C1111.0 (3)C23—C17—C18—C19179.05 (17)
C8—C9—C10—C11A−26.3 (5)C16—C17—C18—C20−179.03 (18)
O1—C10—C11—C2526.1 (3)C23—C17—C18—C200.1 (3)
C9—C10—C11—C25−158.9 (2)C15—C14—C19—C180.5 (3)
C11A—C10—C11—C25−71.3 (5)C12—C14—C19—C18−178.22 (16)
O1—C10—C11—C12145.3 (2)C12A—C14—C19—C18173.1 (5)
C9—C10—C11—C12−39.7 (3)C17—C18—C19—C14−0.2 (3)
C11A—C10—C11—C1247.8 (5)C20—C18—C19—C14178.75 (17)
C25—C11—C12—C14−57.1 (3)C19—C18—C20—C21−179.60 (18)
C10—C11—C12—C14−175.51 (17)C17—C18—C20—C21−0.7 (3)
C25—C11—C12—C13178.57 (17)C18—C20—C21—C220.7 (3)
C10—C11—C12—C1360.1 (2)C20—C21—C22—C23−0.2 (3)
O1—C10—C11A—C12A−150.2 (5)C20—C21—C22—O4179.05 (19)
C9—C10—C11A—C12A60.7 (7)O4—C22—C23—C17−179.54 (19)
C11—C10—C11A—C12A−47.3 (6)C21—C22—C23—C17−0.3 (3)
O1—C10—C11A—C25−42.2 (6)C16—C17—C23—C22179.5 (2)
C9—C10—C11A—C25168.6 (3)C18—C17—C23—C220.4 (3)
C11—C10—C11A—C2560.6 (5)C12—C11—C25—O3−49.0 (3)
C25—C11A—C12A—C13−176.4 (5)C10—C11—C25—O368.9 (3)
C10—C11A—C12A—C13−71.6 (8)C12—C11—C25—O2129.7 (2)
C25—C11A—C12A—C1473.8 (7)C10—C11—C25—O2−112.3 (2)
C10—C11A—C12A—C14178.6 (5)C12—C11—C25—C11A−46.5 (5)
C11A—C12A—C13—C847.6 (8)C10—C11—C25—C11A71.4 (5)
C14—C12A—C13—C8154.4 (4)C12A—C11A—C25—O3−139.3 (6)
C11A—C12A—C13—C12−47.7 (7)C10—C11A—C25—O3117.3 (4)
C14—C12A—C13—C1259.1 (6)C12A—C11A—C25—O236.8 (9)
C9—C8—C13—C12A−6.8 (5)C10—C11A—C25—O2−66.5 (7)
C5—C8—C13—C12A175.4 (5)C12A—C11A—C25—C1142.6 (6)
C9—C8—C13—C1224.9 (2)C10—C11A—C25—C11−60.7 (5)
C5—C8—C13—C12−152.93 (17)O3—C25—O2—C262.4 (3)
C14—C12—C13—C12A−81.3 (7)C11—C25—O2—C26−176.5 (2)
C11—C12—C13—C12A43.3 (7)C11A—C25—O2—C26−173.0 (5)
C14—C12—C13—C8−178.60 (17)C27—C26—O2—C25108.1 (3)
C11—C12—C13—C8−54.1 (2)C23—C22—O4—C24−2.7 (4)
C13—C12—C14—C19−96.6 (2)C21—C22—O4—C24178.0 (2)
C11—C12—C14—C19140.7 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C26—H26A···O3i0.972.423.332 (4)157

Symmetry codes: (i) x, −y+3/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DN2449).

References

  • Bruker (2006). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Fischer, A., Yathirajan, H. S., Ashalatha, B. V., Narayana, B. & Sarojini, B. K. (2007a). Acta Cryst. E63, o254–o255.
  • Fischer, A., Yathirajan, H. S., Ashalatha, B. V., Narayana, B. & Sarojini, B. K. (2007b). Acta Cryst. E63, o3616.
  • Fischer, A., Yathirajan, H. S., Ashalatha, B. V., Narayana, B. & Sarojini, B. K. (2008). Acta Cryst. E64, o560. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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