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In the title compound, C28H19NO4, the configurations of the substituents attached to the oxirane ring are conditioned by the sp3 states of the oxirane C atoms. In the packing, the mol­ecules form zigzag molecular chains along the b direction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802015350/cv6138sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802015350/cv6138Isup2.hkl
Contains datablock I

CCDC reference: 198332

Key indicators

  • Single-crystal X-ray study
  • T = 213 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.066
  • wR factor = 0.155
  • Data-to-parameter ratio = 17.3

checkCIF results

No syntax errors found

Structure: I
------------

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
GOODF_01 Alert C The least squares goodness of fit parameter lies outside the range 0.80 <> 2.00 Goodness of fit given = 0.794 RINTA_01 Alert C The value of Rint is greater than 0.10 Rint given 0.109
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check

Comment top

Photoinduced oxygenation reactions of indolizine derivatives have been investigated intensively in our previous study (Tian et al., 2001). In continuation of that work, we have isolated the title compound, (I), which was obtained from the photo-oxygenation reactions of 1,3-dibenzoyl-2-phenylindolizine. We report here an X-ray crystallographic analysis at 213 K of (I), which was undertaken to establish its conformation and stereochemistry.

The bond lengths and angles observed in (I) (Fig. 1) are within normal ranges (Allen et al., 1987). The values within the oxirane (O3/C9/C16) agree with those of a related structure studied previously (Krishnakumar et al., 2002), except for a slight elongation of the C9—C16 bond [1.509 (3) Å versus 1.488 (4) Å (Krishnakumar et al., 2002)] due to the bulky substituents attached at atoms C9 and C16. The configurations of the substituents are conditioned by these two Csp3 atoms. Except for the bond angles within the oxirane, the average bond angles subtended at atoms C9 and C16 are 117.2 and 116.8°, respectively, while the two atoms are eclipsed, as determined by the torsion angles C8—C9—C16—C17 = 1.4 (3)° and C10—C9—C16—C22 = 4.7 (3)°.

In the dioxophenylethylene moiety (O1/O2/C1–C9), the two carbonyl groups form O1/C6/C7/C8 and O2/C7/C8/C9 planes. These two planes are twisted out of the phenyl ring by 11.7 (1) and 38.8 (1)°, respectively. The O2/C7/C8/C9 plane and the C10–C15 phenyl ring attached at atom C9 form dihedral angles of 56.1 (1) and 63.6 (2)°, respectivley, with the oxirane ring plane.

The pyridine ring (N1/C17–C21) attached at atom C16 is perpendicular to the oxirane ring plane, with a dihedral angle of 88.6 (2)°. The carbonyl group of the benzoyl moiety (O4/C22–C28) attached at the same atom is twisted from its aromatic ring by an angle of 20.8 (1)° and the O4/C16/C22/C23 plane makes a dihedral angle of 61.8 (2)° with the oxirane ring plane.

In the packing, the molecules are interconnected by C21—H21···O4i interactions [H21···O4i 2.56 Å and C21—H21···O4i 129°; symmetry code: (i) 1 − x, y − 1/2, 1/2 − z] into zig-ag molecular chains along the b direction (Fig. 2). These interactions, along with the dipole–dipole and van der Waals interactions, stabilize the packing.

Experimental top

The title compound was prepared by photoinduced oxygenation of 1,3-dibenzoyl-2-phenylindolizine in acetonitrile and was isolated by by column chromatography. Single crystals for X-ray measurement were obtained by slow evaporation of the solvent from a petroleum ether–ethyl acetate (5:1 v/v) solution.

Refinement top

The H atoms were fixed geometrically and were treated as riding on their parent C atoms, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT and SADABS (Sheldrick, 1996); program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

Figures top
[Figure 1] Fig. 1. The structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.
[Figure 2] Fig. 2. Part of packing of the title compound, viewed down the a axis, showing the zigzag molecular chains along the b direction.
2-Benzoyl-3-(1,2-dioxo-2-phenylethyl)-3-phenyl-2-(pyridin-2-yl)oxirane top
Crystal data top
C28H19NO4Dx = 1.330 Mg m3
Mr = 433.44Melting point: 416(1) K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 13.1513 (4) ÅCell parameters from 7367 reflections
b = 9.7358 (3) Åθ = 2.6–28.3°
c = 16.9960 (5) ŵ = 0.09 mm1
β = 95.859 (1)°T = 213 K
V = 2164.8 (1) Å3Slab, colorless
Z = 40.38 × 0.34 × 0.16 mm
F(000) = 904
Data collection top
Siemens SMART CCD area-detector
diffractometer
2808 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.110
Graphite monochromatorθmax = 28.3°, θmin = 2.6°
Detector resolution: 8.33 pixels mm-1h = 1017
ω scansk = 1212
12406 measured reflectionsl = 2222
5164 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)] = 0.066H-atom parameters constrained
wR(F2) = 0.156 w = 1/[σ2(Fo2)]
where P = (Fo2 + 2Fc2)/3
S = 0.79(Δ/σ)max = 0.001
5164 reflectionsΔρmax = 0.34 e Å3
299 parametersΔρmin = 0.28 e Å3
0 restraintsExtinction correction: SHELXTL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.021 (2)
Crystal data top
C28H19NO4V = 2164.8 (1) Å3
Mr = 433.44Z = 4
Monoclinic, P21/cMo Kα radiation
a = 13.1513 (4) ŵ = 0.09 mm1
b = 9.7358 (3) ÅT = 213 K
c = 16.9960 (5) Å0.38 × 0.34 × 0.16 mm
β = 95.859 (1)°
Data collection top
Siemens SMART CCD area-detector
diffractometer
2808 reflections with I > 2σ(I)
12406 measured reflectionsRint = 0.110
5164 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0660 restraints
wR(F2) = 0.156H-atom parameters constrained
S = 0.79Δρmax = 0.34 e Å3
5164 reflectionsΔρmin = 0.28 e Å3
299 parameters
Special details top

Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was −35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible.

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*/Ueq
O10.83526 (14)0.90749 (16)0.20400 (11)0.0486 (5)
O20.92115 (12)0.66777 (17)0.33075 (9)0.0361 (4)
O30.67590 (11)0.71080 (14)0.22032 (8)0.0264 (4)
O40.49983 (11)0.61336 (17)0.27233 (10)0.0392 (4)
N10.81182 (13)0.49306 (18)0.19663 (10)0.0263 (4)
C10.9665 (2)0.8357 (3)0.09045 (15)0.0440 (7)
H10.92370.91090.07970.053*
C21.0363 (2)0.7997 (3)0.03841 (17)0.0566 (8)
H21.03870.84870.00830.068*
C31.1024 (2)0.6912 (3)0.05578 (16)0.0486 (7)
H31.15010.66850.02110.058*
C41.09795 (19)0.6166 (3)0.12394 (14)0.0404 (6)
H41.14280.54380.13550.048*
C51.02657 (17)0.6497 (2)0.17546 (13)0.0316 (5)
H51.02300.59830.22120.038*
C60.96051 (16)0.7591 (2)0.15902 (12)0.0275 (5)
C70.88147 (17)0.7990 (2)0.21090 (13)0.0294 (5)
C80.85547 (17)0.7092 (2)0.28065 (12)0.0249 (5)
C90.74207 (15)0.7085 (2)0.29277 (11)0.0210 (4)
C100.71388 (16)0.7979 (2)0.35897 (12)0.0239 (5)
C110.76665 (17)0.7884 (2)0.43381 (12)0.0304 (5)
H110.81930.72490.44340.037*
C120.7411 (2)0.8733 (2)0.49448 (14)0.0377 (6)
H120.77610.86520.54470.045*
C130.6650 (2)0.9688 (3)0.48098 (15)0.0437 (7)
H130.64891.02600.52180.052*
C140.6119 (2)0.9804 (3)0.40648 (16)0.0464 (7)
H140.56001.04500.39740.056*
C150.63636 (18)0.8950 (2)0.34505 (14)0.0361 (6)
H150.60100.90290.29500.043*
C160.67753 (15)0.5858 (2)0.26576 (12)0.0216 (4)
C170.72551 (15)0.4641 (2)0.22897 (11)0.0220 (4)
C180.85871 (17)0.3884 (2)0.16420 (13)0.0306 (5)
H180.91780.40700.14030.037*
C190.82440 (17)0.2545 (2)0.16420 (13)0.0324 (5)
H190.86090.18450.14270.039*
C200.73523 (18)0.2268 (2)0.19662 (13)0.0339 (5)
H200.70980.13770.19680.041*
C210.68369 (17)0.3330 (2)0.22905 (12)0.0281 (5)
H210.62240.31710.25040.034*
C220.57872 (15)0.5610 (2)0.30276 (12)0.0243 (5)
C230.57974 (16)0.4714 (2)0.37314 (12)0.0254 (5)
C240.66999 (18)0.4470 (2)0.42211 (13)0.0328 (5)
H240.73160.48280.40900.039*
C250.6673 (2)0.3698 (3)0.48981 (14)0.0454 (7)
H250.72710.35550.52300.054*
C260.5767 (2)0.3136 (3)0.50886 (15)0.0474 (7)
H260.57550.26250.55500.057*
C270.4878 (2)0.3332 (3)0.45943 (16)0.0441 (7)
H270.42720.29240.47120.053*
C280.48887 (19)0.4135 (2)0.39230 (14)0.0364 (6)
H280.42860.42880.35990.044*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0510 (12)0.0288 (10)0.0709 (13)0.0073 (8)0.0296 (10)0.0055 (8)
O20.0186 (8)0.0565 (11)0.0322 (9)0.0007 (7)0.0020 (7)0.0023 (8)
O30.0256 (8)0.0261 (8)0.0261 (7)0.0029 (6)0.0042 (6)0.0033 (6)
O40.0160 (8)0.0451 (10)0.0550 (11)0.0062 (7)0.0044 (8)0.0036 (8)
N10.0194 (10)0.0310 (10)0.0288 (9)0.0010 (8)0.0047 (8)0.0033 (7)
C10.0403 (15)0.0440 (15)0.0505 (15)0.0043 (12)0.0175 (13)0.0145 (12)
C20.058 (2)0.064 (2)0.0530 (17)0.0033 (15)0.0274 (15)0.0168 (14)
C30.0387 (16)0.0563 (18)0.0549 (17)0.0005 (13)0.0248 (14)0.0006 (13)
C40.0277 (14)0.0475 (15)0.0474 (15)0.0056 (11)0.0101 (12)0.0001 (12)
C50.0235 (12)0.0359 (13)0.0351 (12)0.0004 (10)0.0022 (10)0.0008 (10)
C60.0213 (12)0.0287 (12)0.0328 (11)0.0063 (9)0.0036 (9)0.0025 (9)
C70.0277 (13)0.0238 (12)0.0375 (12)0.0040 (9)0.0071 (10)0.0044 (9)
C80.0228 (12)0.0240 (11)0.0281 (11)0.0008 (9)0.0033 (9)0.0054 (8)
C90.0157 (10)0.0240 (11)0.0225 (10)0.0024 (8)0.0018 (8)0.0009 (8)
C100.0214 (11)0.0215 (11)0.0293 (11)0.0020 (8)0.0054 (9)0.0009 (8)
C110.0272 (13)0.0317 (12)0.0322 (12)0.0028 (9)0.0015 (10)0.0050 (9)
C120.0430 (16)0.0394 (14)0.0311 (13)0.0055 (11)0.0049 (11)0.0093 (10)
C130.0546 (18)0.0355 (14)0.0440 (15)0.0004 (12)0.0189 (13)0.0140 (11)
C140.0450 (17)0.0384 (15)0.0569 (17)0.0167 (12)0.0109 (14)0.0090 (12)
C150.0317 (14)0.0355 (13)0.0406 (13)0.0075 (10)0.0018 (11)0.0043 (10)
C160.0157 (10)0.0233 (11)0.0250 (10)0.0029 (8)0.0021 (8)0.0001 (8)
C170.0153 (10)0.0288 (11)0.0209 (10)0.0011 (8)0.0023 (8)0.0019 (8)
C180.0220 (12)0.0392 (13)0.0315 (12)0.0021 (10)0.0064 (10)0.0068 (10)
C190.0261 (13)0.0368 (13)0.0341 (12)0.0080 (10)0.0017 (10)0.0089 (10)
C200.0336 (14)0.0280 (12)0.0396 (13)0.0014 (10)0.0016 (11)0.0078 (10)
C210.0206 (12)0.0305 (12)0.0336 (12)0.0031 (9)0.0043 (9)0.0062 (9)
C220.0132 (10)0.0268 (11)0.0319 (11)0.0010 (8)0.0033 (9)0.0064 (8)
C230.0200 (11)0.0247 (11)0.0325 (12)0.0001 (9)0.0075 (9)0.0060 (9)
C240.0260 (13)0.0385 (13)0.0346 (13)0.0053 (10)0.0058 (10)0.0022 (10)
C250.0475 (17)0.0504 (16)0.0394 (14)0.0162 (13)0.0102 (13)0.0103 (12)
C260.067 (2)0.0333 (14)0.0461 (15)0.0097 (13)0.0273 (15)0.0060 (11)
C270.0478 (17)0.0324 (14)0.0572 (17)0.0095 (12)0.0297 (14)0.0076 (12)
C280.0263 (13)0.0372 (14)0.0471 (14)0.0051 (10)0.0101 (11)0.0119 (11)
Geometric parameters (Å, º) top
O1—C71.218 (3)C12—H120.9300
O2—C81.218 (3)C13—C141.387 (4)
O3—C91.434 (2)C13—H130.9300
O3—C161.441 (2)C14—C151.398 (3)
O4—C221.222 (2)C14—H140.9300
N1—C181.339 (3)C15—H150.9300
N1—C171.341 (2)C16—C171.507 (3)
C1—C21.383 (3)C16—C221.520 (3)
C1—C61.393 (3)C17—C211.390 (3)
C1—H10.9300C18—C191.379 (3)
C2—C31.381 (4)C18—H180.9300
C2—H20.9300C19—C201.372 (3)
C3—C41.374 (3)C19—H190.9300
C3—H30.9300C20—C211.381 (3)
C4—C51.386 (3)C20—H200.9300
C4—H40.9300C21—H210.9300
C5—C61.385 (3)C22—C231.479 (3)
C5—H50.9300C23—C281.390 (3)
C6—C71.482 (3)C23—C241.399 (3)
C7—C81.539 (3)C24—C251.378 (3)
C8—C91.526 (3)C24—H240.9300
C9—C101.499 (3)C25—C261.379 (4)
C9—C161.509 (3)C25—H250.9300
C10—C111.389 (3)C26—C271.382 (4)
C10—C151.392 (3)C26—H260.9300
C11—C121.389 (3)C27—C281.385 (3)
C11—H110.9300C27—H270.9300
C12—C131.368 (4)C28—H280.9300
C9—O3—C1663.36 (12)C15—C14—H14120.0
C18—N1—C17116.97 (18)C10—C15—C14119.8 (2)
C2—C1—C6119.8 (2)C10—C15—H15120.1
C2—C1—H1120.1C14—C15—H15120.1
C6—C1—H1120.1O3—C16—C17115.18 (15)
C3—C2—C1120.1 (2)O3—C16—C958.09 (12)
C3—C2—H2120.0C17—C16—C9120.12 (17)
C1—C2—H2120.0O3—C16—C22112.92 (16)
C4—C3—C2120.4 (2)C17—C16—C22117.30 (17)
C4—C3—H3119.8C9—C16—C22118.55 (16)
C2—C3—H3119.8N1—C17—C21123.03 (19)
C3—C4—C5120.0 (2)N1—C17—C16114.36 (18)
C3—C4—H4120.0C21—C17—C16122.60 (18)
C5—C4—H4120.0N1—C18—C19123.7 (2)
C6—C5—C4120.2 (2)N1—C18—H18118.1
C6—C5—H5119.9C19—C18—H18118.1
C4—C5—H5119.9C20—C19—C18118.6 (2)
C5—C6—C1119.6 (2)C20—C19—H19120.7
C5—C6—C7123.0 (2)C18—C19—H19120.7
C1—C6—C7117.4 (2)C19—C20—C21119.2 (2)
O1—C7—C6122.9 (2)C19—C20—H20120.4
O1—C7—C8114.74 (19)C21—C20—H20120.4
C6—C7—C8122.26 (19)C20—C21—C17118.5 (2)
O2—C8—C9122.47 (18)C20—C21—H21120.8
O2—C8—C7121.9 (2)C17—C21—H21120.8
C9—C8—C7113.81 (18)O4—C22—C23121.69 (19)
O3—C9—C10117.42 (16)O4—C22—C16118.90 (19)
O3—C9—C1658.55 (12)C23—C22—C16119.38 (17)
C10—C9—C16120.90 (17)C28—C23—C24119.3 (2)
O3—C9—C8113.57 (15)C28—C23—C22119.4 (2)
C10—C9—C8114.73 (17)C24—C23—C22121.21 (19)
C16—C9—C8119.33 (16)C25—C24—C23119.8 (2)
C11—C10—C15119.31 (19)C25—C24—H24120.1
C11—C10—C9120.68 (18)C23—C24—H24120.1
C15—C10—C9120.0 (2)C24—C25—C26120.6 (3)
C10—C11—C12120.3 (2)C24—C25—H25119.7
C10—C11—H11119.9C26—C25—H25119.7
C12—C11—H11119.9C25—C26—C27120.0 (2)
C13—C12—C11120.5 (2)C25—C26—H26120.0
C13—C12—H12119.7C27—C26—H26120.0
C11—C12—H12119.7C26—C27—C28120.0 (2)
C12—C13—C14120.0 (2)C26—C27—H27120.0
C12—C13—H13120.0C28—C27—H27120.0
C14—C13—H13120.0C27—C28—C23120.2 (2)
C13—C14—C15120.1 (2)C27—C28—H28119.9
C13—C14—H14120.0C23—C28—H28119.9
C6—C1—C2—C32.3 (4)C10—C9—C16—O3105.3 (2)
C1—C2—C3—C41.3 (5)C8—C9—C16—O3101.19 (18)
C2—C3—C4—C50.3 (4)O3—C9—C16—C17102.61 (18)
C3—C4—C5—C60.9 (4)C10—C9—C16—C17152.14 (18)
C4—C5—C6—C10.1 (4)C8—C9—C16—C171.4 (3)
C4—C5—C6—C7179.1 (2)O3—C9—C16—C22100.58 (18)
C2—C1—C6—C51.7 (4)C10—C9—C16—C224.7 (3)
C2—C1—C6—C7177.6 (2)C8—C9—C16—C22158.24 (18)
C5—C6—C7—O1167.3 (2)C18—N1—C17—C210.8 (3)
C1—C6—C7—O113.4 (3)C18—N1—C17—C16178.94 (18)
C5—C6—C7—C89.4 (3)O3—C16—C17—N142.7 (2)
C1—C6—C7—C8169.8 (2)C9—C16—C17—N123.6 (3)
O1—C7—C8—O2125.2 (2)C22—C16—C17—N1179.31 (17)
C6—C7—C8—O251.8 (3)O3—C16—C17—C21137.6 (2)
O1—C7—C8—C940.0 (3)C9—C16—C17—C21156.13 (19)
C6—C7—C8—C9143.0 (2)C22—C16—C17—C211.0 (3)
C16—O3—C9—C10111.15 (19)C17—N1—C18—C191.6 (3)
C16—O3—C9—C8111.08 (18)N1—C18—C19—C202.4 (4)
O2—C8—C9—O3157.78 (19)C18—C19—C20—C210.9 (3)
C7—C8—C9—O337.1 (2)C19—C20—C21—C171.3 (3)
O2—C8—C9—C1063.3 (3)N1—C17—C21—C202.2 (3)
C7—C8—C9—C10101.9 (2)C16—C17—C21—C20177.50 (19)
O2—C8—C9—C1691.9 (2)O3—C16—C22—O424.6 (3)
C7—C8—C9—C16103.0 (2)C17—C16—C22—O4113.0 (2)
O3—C9—C10—C11171.87 (17)C9—C16—C22—O489.6 (2)
C16—C9—C10—C11103.9 (2)O3—C16—C22—C23157.05 (17)
C8—C9—C10—C1150.8 (2)C17—C16—C22—C2365.4 (2)
O3—C9—C10—C1510.3 (3)C9—C16—C22—C2392.1 (2)
C16—C9—C10—C1578.3 (3)O4—C22—C23—C2818.5 (3)
C8—C9—C10—C15127.0 (2)C16—C22—C23—C28159.85 (18)
C15—C10—C11—C121.1 (3)O4—C22—C23—C24159.6 (2)
C9—C10—C11—C12178.9 (2)C16—C22—C23—C2422.0 (3)
C10—C11—C12—C131.1 (4)C28—C23—C24—C252.0 (3)
C11—C12—C13—C140.7 (4)C22—C23—C24—C25176.1 (2)
C12—C13—C14—C150.3 (4)C23—C24—C25—C261.5 (4)
C11—C10—C15—C140.7 (3)C24—C25—C26—C270.7 (4)
C9—C10—C15—C14178.5 (2)C25—C26—C27—C282.4 (4)
C13—C14—C15—C100.3 (4)C26—C27—C28—C231.9 (3)
C9—O3—C16—C17111.12 (19)C24—C23—C28—C270.3 (3)
C9—O3—C16—C22110.36 (18)C22—C23—C28—C27177.82 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O20.932.503.109 (3)124
C11—H11···O20.932.513.050 (3)117
C21—H21···O4i0.932.563.223 (3)129
Symmetry code: (i) x+1, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC28H19NO4
Mr433.44
Crystal system, space groupMonoclinic, P21/c
Temperature (K)213
a, b, c (Å)13.1513 (4), 9.7358 (3), 16.9960 (5)
β (°) 95.859 (1)
V3)2164.8 (1)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.38 × 0.34 × 0.16
Data collection
DiffractometerSiemens SMART CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
12406, 5164, 2808
Rint0.110
(sin θ/λ)max1)0.666
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.066, 0.156, 0.79
No. of reflections5164
No. of parameters299
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.34, 0.28

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT and SADABS (Sheldrick, 1996), SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).

Selected geometric parameters (Å, º) top
O3—C91.434 (2)O3—C161.441 (2)
O3—C9—C10117.42 (16)O3—C16—C17115.18 (15)
C10—C9—C16120.90 (17)C17—C16—C9120.12 (17)
O3—C9—C8113.57 (15)O3—C16—C22112.92 (16)
C10—C9—C8114.73 (17)C17—C16—C22117.30 (17)
C16—C9—C8119.33 (16)C9—C16—C22118.55 (16)
 

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