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Acta Cryst. (2009). E65, o1186    [ doi:10.1107/S1600536809016341 ]

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

H. Li, A. N. Mayekar, B. Narayana, H. S. Yathirajan and W. T. A. Harrison

Abstract top

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.

Comment top

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.

Related literature top

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

Experimental top

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 top

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.

Computing details top

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

Figures top
[Figure 1] 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.
(±)-Ethyl 6-(6-methoxy-2-naphthyl)-4-(4-methylphenyl)-2-oxocyclohex-3-ene-1-carboxylate top
Crystal data top
C27H26O4F000 = 880
Mr = 414.48Dx = 1.262 Mg m−3
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 = 2.3–28.1º
c = 10.2356 (6) ŵ = 0.08 mm−1
β = 93.430 (2)ºT = 296 K
V = 2182.3 (2) Å3Block, colorless
Z = 40.44 × 0.38 × 0.22 mm
Data collection top
Bruker SMART CCD
diffractometer		3385 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.024
Monochromator: graphiteθmax = 26.0º
T = 296 Kθmin = 2.1º
ω scansh = −22→23
Absorption correction: nonek = −14→13
26105 measured reflectionsl = −12→12
4269 independent 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)] = 0.050H-atom parameters constrained
wR(F2) = 0.147  w = 1/[σ2(Fo2) + (0.0575P)2 + 0.796P]
where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
4269 reflectionsΔρmax = 0.28 e Å−3
292 parametersΔρmin = −0.23 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C27H26O4V = 2182.3 (2) Å3
Mr = 414.48Z = 4
Monoclinic, P21/cMo Kα
a = 18.8013 (10) ŵ = 0.08 mm−1
b = 11.3604 (6) ÅT = 296 K
c = 10.2356 (6) Å0.44 × 0.38 × 0.22 mm
β = 93.430 (2)º
Data collection top
Bruker SMART CCD
diffractometer		4269 independent reflections
Absorption correction: none3385 reflections with I > 2σ(I)
26105 measured reflectionsRint = 0.024
Refinement top
R[F2 > 2σ(F2)] = 0.050292 parameters
wR(F2) = 0.147H-atom parameters constrained
S = 1.08Δρmax = 0.28 e Å−3
4269 reflectionsΔρmin = −0.23 e Å−3
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.

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) top
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) top
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, °) top
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, °) top
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.
Table 1
Hydrogen-bond geometry (Å, °) top
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.
Acknowledgements top

ANM thanks the University of Mysore for research facilities.

references
References top

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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.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.