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Acta Cryst. (2009). E65, o588    [ doi:10.1107/S1600536809005145 ]

trans-1,2,3-Tris(4-methoxybenzoyl)cyclopropane

J. Sun and N. She

Abstract top

In the title compound, C27H24O6, the packing of the molecules is mainly governed by C-H...O interactions.

Comment top

The unusual bonding of cyclopropanes and the strain release associated with cleavage of cyclopropanes offer the possibility of recognizing that structural unit when it is a part of a larger molecule. We report here the molecular structure of the title cyclopropane derivative (Fig. 1), which is an important intermediate in organic synthesis (Saba, 1990). Since numerous methodologies have been developed for the construction of three–membered carbocycles, the chemistry of cyclopropanes has emerged as a versatile tool in organic synthesis (Wong, 1989).

The crystal packing is stabilized by intermolecular C—H···O interaction.

Related literature top

For related structures, see: Saba (1990). For background to the chemistry of cyclopropanes as a versatile tool in organic synthesis, see: Wong (1989).

Experimental top

The title compound was synthesized according to the procedure reported (Saba, 1990). Crystals appropriate for X–ray data collection were obtained by slow evaporation of the dichloromethane solution at 293 K.

Refinement top

All H atoms were positioned in geometrically idealized positions and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.98 Å with Uiso(H) = 1.2Ueq(C) or Uiso(H) = 1.5Ueq(C).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom–numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as a small spheres of arbitrary radius.
trans-1,2,3-Tris(4-methoxybenzoyl)cyclopropane top
Crystal data top
C27H24O6Z = 2
Mr = 444.46F(000) = 468
Triclinic, P1Dx = 1.311 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.1897 (6) ÅCell parameters from 1774 reflections
b = 10.626 (6) Åθ = 2.7–21.3°
c = 10.6931 (6) ŵ = 0.09 mm−1
α = 90.736 (1)°T = 298 K
β = 103.194 (1)°Block, colourless
γ = 92.432 (1)°0.30 × 0.20 × 0.10 mm
V = 1125.9 (6) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer		2862 reflections with I > 2σ(I)
Radiation source: Fine–focus sealed tubeRint = 0.031
Graphiteθmax = 26.0°, θmin = 1.9°
φ and ω scansh = −12→12
9852 measured reflectionsk = −10→13
4349 independent reflectionsl = −13→13
Refinement top
Refinement on F2Primary atom site location: Direct
Least-squares matrix: FullSecondary atom site location: Difmap
R[F2 > 2σ(F2)] = 0.057Hydrogen site location: Geom
wR(F2) = 0.155H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0697P)2 + 0.0779P]
where P = (Fo2 + 2Fc2)/3
4349 reflections(Δ/σ)max = 0.001
301 parametersΔρmax = 0.19 e Å−3
0 restraintsΔρmin = −0.17 e Å−3
Crystal data top
C27H24O6γ = 92.432 (1)°
Mr = 444.46V = 1125.9 (6) Å3
Triclinic, P1Z = 2
a = 10.1897 (6) ÅMo Kα radiation
b = 10.626 (6) ŵ = 0.09 mm−1
c = 10.6931 (6) ÅT = 298 K
α = 90.736 (1)°0.30 × 0.20 × 0.10 mm
β = 103.194 (1)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		2862 reflections with I > 2σ(I)
9852 measured reflectionsRint = 0.031
4349 independent reflectionsθmax = 26.0°
Refinement top
R[F2 > 2σ(F2)] = 0.057H-atom parameters constrained
wR(F2) = 0.155Δρmax = 0.19 e Å−3
S = 1.06Δρmin = −0.17 e Å−3
4349 reflectionsAbsolute structure: ?
301 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
C11.0074 (3)1.5583 (3)0.2073 (3)0.0938 (10)
H1A0.93401.61410.19030.141*
H1B1.07731.58920.16720.141*
H1C1.04251.55430.29830.141*
C20.8628 (2)1.3733 (2)0.2028 (2)0.0559 (6)
C30.8010 (3)1.4209 (2)0.2944 (2)0.0632 (7)
H30.82561.50110.33020.076*
C40.7018 (3)1.3478 (2)0.3320 (2)0.0598 (7)
H40.66271.37840.39610.072*
C50.6594 (2)1.2303 (2)0.27708 (19)0.0452 (6)
C60.7213 (2)1.1851 (2)0.1834 (2)0.0480 (6)
H60.69351.10700.14400.058*
C70.8233 (2)1.2554 (2)0.1489 (2)0.0578 (7)
H70.86621.22290.08840.069*
C80.5550 (2)1.1548 (2)0.32226 (19)0.0489 (6)
C90.4782 (2)1.0509 (2)0.23775 (18)0.0447 (6)
H90.45601.06680.14540.054*
C100.3734 (2)0.9763 (2)0.28795 (19)0.0453 (6)
H100.36940.99790.37630.054*
C110.5019 (2)0.9174 (2)0.27438 (19)0.0452 (6)
H110.56810.90610.35520.054*
C120.5012 (2)0.8198 (2)0.1703 (2)0.0480 (6)
C130.4473 (2)0.6911 (2)0.1861 (2)0.0467 (6)
C140.4281 (3)0.6476 (3)0.3027 (2)0.0592 (7)
H140.45150.69990.37560.071*
C150.3747 (3)0.5276 (3)0.3114 (2)0.0684 (8)
H150.36430.49890.39050.082*
C160.3365 (3)0.4493 (2)0.2036 (2)0.0571 (6)
C170.3553 (3)0.4921 (3)0.0870 (2)0.0578 (7)
H170.32940.44090.01350.069*
C180.4123 (2)0.6105 (2)0.0802 (2)0.0529 (6)
H180.42780.63720.00210.064*
C190.2147 (3)0.2623 (3)0.1091 (3)0.0829 (9)
H19A0.15270.31310.05230.124*
H19B0.16630.19120.13430.124*
H19C0.28100.23340.06590.124*
C200.2404 (2)0.9402 (2)0.20001 (19)0.0437 (6)
C210.1269 (2)0.9056 (2)0.25933 (19)0.0425 (5)
C22−0.0052 (2)0.9130 (2)0.1882 (2)0.0503 (6)
H22−0.02110.93940.10370.060*
C23−0.1126 (2)0.8816 (2)0.2419 (2)0.0582 (7)
H23−0.20030.88750.19360.070*
C24−0.0906 (2)0.8411 (2)0.3674 (2)0.0538 (6)
C250.0391 (2)0.8319 (3)0.4392 (2)0.0593 (7)
H250.05450.80390.52310.071*
C260.1462 (2)0.8650 (2)0.3847 (2)0.0534 (6)
H260.23370.85980.43370.064*
C27−0.1880 (3)0.7676 (3)0.5382 (3)0.0860 (9)
H27A−0.14110.69060.54570.129*
H27B−0.27530.75240.55630.129*
H27C−0.13720.82950.59820.129*
O20.53287 (17)1.17456 (18)0.42848 (14)0.0672 (5)
O10.96041 (19)1.43598 (18)0.15687 (19)0.0816 (6)
O30.54286 (18)0.84862 (17)0.07605 (15)0.0635 (5)
O40.2801 (2)0.33557 (18)0.22053 (17)0.0786 (6)
O50.22625 (15)0.94253 (16)0.08352 (13)0.0579 (5)
O6−0.20364 (17)0.8128 (2)0.41048 (18)0.0797 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.086 (2)0.058 (2)0.140 (3)−0.0223 (17)0.036 (2)−0.0041 (19)
C20.0474 (14)0.0519 (16)0.0689 (15)−0.0061 (12)0.0160 (12)0.0002 (12)
C30.0651 (16)0.0477 (17)0.0761 (17)−0.0103 (13)0.0178 (13)−0.0154 (13)
C40.0622 (15)0.0631 (18)0.0557 (14)−0.0040 (13)0.0191 (12)−0.0128 (12)
C50.0447 (12)0.0474 (15)0.0409 (11)−0.0032 (11)0.0057 (9)0.0003 (10)
C60.0504 (13)0.0439 (14)0.0487 (12)−0.0027 (11)0.0103 (10)−0.0032 (10)
C70.0532 (14)0.0607 (18)0.0636 (15)−0.0030 (13)0.0233 (12)−0.0097 (12)
C80.0461 (13)0.0625 (17)0.0343 (11)0.0013 (11)0.0016 (9)0.0022 (10)
C90.0431 (12)0.0574 (16)0.0320 (10)−0.0077 (11)0.0073 (9)0.0032 (10)
C100.0432 (12)0.0569 (15)0.0354 (10)−0.0034 (11)0.0094 (9)−0.0037 (10)
C110.0382 (12)0.0564 (16)0.0388 (11)−0.0011 (10)0.0047 (9)0.0037 (10)
C120.0381 (12)0.0635 (17)0.0435 (12)0.0040 (11)0.0115 (10)0.0020 (11)
C130.0441 (12)0.0542 (16)0.0445 (12)0.0069 (11)0.0149 (10)0.0039 (10)
C140.0696 (17)0.0643 (19)0.0442 (13)−0.0035 (14)0.0154 (11)0.0006 (11)
C150.091 (2)0.071 (2)0.0454 (13)−0.0064 (16)0.0213 (13)0.0065 (13)
C160.0659 (16)0.0509 (17)0.0565 (14)0.0060 (13)0.0171 (12)0.0070 (12)
C170.0695 (17)0.0575 (18)0.0483 (13)0.0088 (13)0.0168 (12)−0.0048 (12)
C180.0595 (15)0.0570 (17)0.0471 (13)0.0121 (13)0.0205 (11)0.0042 (11)
C190.099 (2)0.061 (2)0.086 (2)−0.0007 (17)0.0178 (17)−0.0101 (15)
C200.0434 (12)0.0473 (15)0.0403 (12)0.0001 (10)0.0101 (9)−0.0047 (10)
C210.0397 (12)0.0444 (14)0.0428 (11)−0.0024 (10)0.0089 (9)−0.0008 (10)
C220.0469 (13)0.0543 (16)0.0471 (12)−0.0035 (11)0.0063 (10)0.0066 (11)
C230.0384 (13)0.0705 (18)0.0630 (15)0.0004 (12)0.0056 (11)0.0106 (13)
C240.0415 (13)0.0589 (17)0.0637 (15)0.0017 (11)0.0169 (11)0.0124 (12)
C250.0526 (15)0.0770 (19)0.0490 (13)0.0006 (13)0.0128 (11)0.0148 (12)
C260.0381 (12)0.0714 (18)0.0478 (13)−0.0002 (12)0.0042 (10)0.0080 (12)
C270.0723 (19)0.111 (3)0.086 (2)0.0035 (18)0.0399 (16)0.0242 (18)
O20.0693 (11)0.0922 (14)0.0383 (9)−0.0202 (10)0.0137 (8)−0.0112 (8)
O10.0740 (13)0.0648 (14)0.1145 (15)−0.0186 (10)0.0440 (11)−0.0110 (11)
O30.0715 (11)0.0723 (13)0.0538 (9)−0.0054 (9)0.0307 (8)0.0021 (8)
O40.1083 (16)0.0589 (13)0.0671 (11)−0.0104 (11)0.0191 (10)0.0065 (9)
O50.0540 (10)0.0799 (13)0.0384 (8)−0.0060 (9)0.0097 (7)−0.0086 (8)
O60.0481 (10)0.1137 (17)0.0840 (13)0.0054 (10)0.0268 (9)0.0337 (11)
Geometric parameters (Å, °) top
C1—O11.422 (3)C14—C151.378 (3)
C1—H1A0.9600C14—H140.9300
C1—H1B0.9600C15—C161.383 (3)
C1—H1C0.9600C15—H150.9300
C2—O11.360 (3)C16—O41.348 (3)
C2—C71.377 (3)C16—C171.384 (3)
C2—C31.381 (3)C17—C181.373 (3)
C3—C41.383 (3)C17—H170.9300
C3—H30.9300C18—H180.9300
C4—C51.381 (3)C19—O41.428 (3)
C4—H40.9300C19—H19A0.9600
C5—C61.390 (3)C19—H19B0.9600
C5—C81.477 (3)C19—H19C0.9600
C6—C71.376 (3)C20—O51.222 (2)
C6—H60.9300C20—C211.477 (3)
C7—H70.9300C21—C261.387 (3)
C8—O21.225 (2)C21—C221.393 (3)
C8—C91.492 (3)C22—C231.378 (3)
C9—C111.491 (3)C22—H220.9300
C9—C101.503 (3)C23—C241.387 (3)
C9—H90.9800C23—H230.9300
C10—C201.494 (3)C24—O61.358 (3)
C10—C111.510 (3)C24—C251.376 (3)
C10—H100.9800C25—C261.384 (3)
C11—C121.510 (3)C25—H250.9300
C11—H110.9800C26—H260.9300
C12—O31.218 (2)C27—O61.430 (3)
C12—C131.478 (3)C27—H27A0.9600
C13—C181.382 (3)C27—H27B0.9600
C13—C141.387 (3)C27—H27C0.9600
O1—C1—H1A109.5C15—C14—C13120.5 (2)
O1—C1—H1B109.5C15—C14—H14119.8
H1A—C1—H1B109.5C13—C14—H14119.8
O1—C1—H1C109.5C14—C15—C16120.7 (2)
H1A—C1—H1C109.5C14—C15—H15119.6
H1B—C1—H1C109.5C16—C15—H15119.6
O1—C2—C7115.4 (2)O4—C16—C15116.4 (2)
O1—C2—C3124.8 (2)O4—C16—C17124.5 (2)
C7—C2—C3119.8 (2)C15—C16—C17119.1 (2)
C2—C3—C4119.1 (2)C18—C17—C16119.7 (2)
C2—C3—H3120.5C18—C17—H17120.2
C4—C3—H3120.5C16—C17—H17120.2
C5—C4—C3121.8 (2)C17—C18—C13121.8 (2)
C5—C4—H4119.1C17—C18—H18119.1
C3—C4—H4119.1C13—C18—H18119.1
C4—C5—C6118.1 (2)O4—C19—H19A109.5
C4—C5—C8119.8 (2)O4—C19—H19B109.5
C6—C5—C8122.0 (2)H19A—C19—H19B109.5
C7—C6—C5120.3 (2)O4—C19—H19C109.5
C7—C6—H6119.8H19A—C19—H19C109.5
C5—C6—H6119.8H19B—C19—H19C109.5
C6—C7—C2120.8 (2)O5—C20—C21121.68 (18)
C6—C7—H7119.6O5—C20—C10120.80 (19)
C2—C7—H7119.6C21—C20—C10117.50 (17)
O2—C8—C5121.07 (19)C26—C21—C22117.9 (2)
O2—C8—C9119.9 (2)C26—C21—C20122.47 (19)
C5—C8—C9119.03 (18)C22—C21—C20119.67 (19)
C11—C9—C8119.55 (18)C23—C22—C21120.6 (2)
C11—C9—C1060.57 (15)C23—C22—H22119.7
C8—C9—C10117.15 (17)C21—C22—H22119.7
C11—C9—H9116.0C22—C23—C24120.4 (2)
C8—C9—H9116.0C22—C23—H23119.8
C10—C9—H9116.0C24—C23—H23119.8
C20—C10—C9119.72 (17)O6—C24—C25124.6 (2)
C20—C10—C11121.69 (18)O6—C24—C23115.4 (2)
C9—C10—C1159.33 (14)C25—C24—C23120.0 (2)
C20—C10—H10114.9C24—C25—C26119.1 (2)
C9—C10—H10114.9C24—C25—H25120.5
C11—C10—H10114.9C26—C25—H25120.5
C9—C11—C1060.10 (15)C25—C26—C21122.0 (2)
C9—C11—C12118.96 (18)C25—C26—H26119.0
C10—C11—C12121.17 (17)C21—C26—H26119.0
C9—C11—H11115.2O6—C27—H27A109.5
C10—C11—H11115.2O6—C27—H27B109.5
C12—C11—H11115.2H27A—C27—H27B109.5
O3—C12—C13121.9 (2)O6—C27—H27C109.5
O3—C12—C11119.9 (2)H27A—C27—H27C109.5
C13—C12—C11118.13 (19)H27B—C27—H27C109.5
C18—C13—C14118.1 (2)C2—O1—C1119.2 (2)
C18—C13—C12119.0 (2)C16—O4—C19118.2 (2)
C14—C13—C12122.9 (2)C24—O6—C27118.2 (2)
O1—C2—C3—C4179.4 (2)C18—C13—C14—C15−0.5 (4)
C7—C2—C3—C41.2 (4)C12—C13—C14—C15178.6 (2)
C2—C3—C4—C5−2.5 (4)C13—C14—C15—C16−1.4 (4)
C3—C4—C5—C61.4 (4)C14—C15—C16—O4−177.3 (2)
C3—C4—C5—C8178.9 (2)C14—C15—C16—C171.4 (4)
C4—C5—C6—C71.1 (3)O4—C16—C17—C18179.2 (2)
C8—C5—C6—C7−176.4 (2)C15—C16—C17—C180.6 (4)
C5—C6—C7—C2−2.3 (4)C16—C17—C18—C13−2.5 (4)
O1—C2—C7—C6−177.2 (2)C14—C13—C18—C172.5 (4)
C3—C2—C7—C61.1 (4)C12—C13—C18—C17−176.6 (2)
C4—C5—C8—O2−21.4 (3)C9—C10—C20—O518.0 (3)
C6—C5—C8—O2156.0 (2)C11—C10—C20—O5−52.3 (3)
C4—C5—C8—C9160.2 (2)C9—C10—C20—C21−160.3 (2)
C6—C5—C8—C9−22.4 (3)C11—C10—C20—C21129.4 (2)
O2—C8—C9—C11−68.5 (3)O5—C20—C21—C26159.8 (2)
C5—C8—C9—C11109.9 (2)C10—C20—C21—C26−21.9 (3)
O2—C8—C9—C101.3 (3)O5—C20—C21—C22−20.1 (3)
C5—C8—C9—C10179.8 (2)C10—C20—C21—C22158.2 (2)
C11—C9—C10—C20−111.4 (2)C26—C21—C22—C230.4 (3)
C8—C9—C10—C20138.3 (2)C20—C21—C22—C23−179.7 (2)
C8—C9—C10—C11−110.3 (2)C21—C22—C23—C24−0.5 (4)
C8—C9—C11—C10106.4 (2)C22—C23—C24—O6179.9 (2)
C8—C9—C11—C12−142.2 (2)C22—C23—C24—C25−0.1 (4)
C10—C9—C11—C12111.4 (2)O6—C24—C25—C26−179.3 (2)
C20—C10—C11—C9108.1 (2)C23—C24—C25—C260.7 (4)
C20—C10—C11—C120.4 (3)C24—C25—C26—C21−0.8 (4)
C9—C10—C11—C12−107.8 (2)C22—C21—C26—C250.3 (4)
C9—C11—C12—O333.7 (3)C20—C21—C26—C25−179.6 (2)
C10—C11—C12—O3104.4 (3)C7—C2—O1—C1−179.9 (3)
C9—C11—C12—C13−145.5 (2)C3—C2—O1—C11.9 (4)
C10—C11—C12—C13−74.8 (3)C15—C16—O4—C19167.5 (2)
O3—C12—C13—C18−16.1 (3)C17—C16—O4—C19−11.1 (4)
C11—C12—C13—C18163.0 (2)C25—C24—O6—C27−1.4 (4)
O3—C12—C13—C14164.8 (2)C23—C24—O6—C27178.6 (3)
C11—C12—C13—C14−16.0 (3)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C26—H26···O2i0.932.543.467 (3)175
C11—H11···O6ii0.982.513.270 (3)134
C7—H7···O5iii0.932.523.171 (3)128
C9—H9···O3iii0.982.553.497 (3)164
C27—H27B···O4iv0.962.583.136 (3)117
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x+1, y, z; (iii) −x+1, −y+2, −z; (iv) −x, −y+1, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C26—H26···O2i0.932.543.467 (3)175
C11—H11···O6ii0.982.513.270 (3)134
C7—H7···O5iii0.932.523.171 (3)128
C9—H9···O3iii0.982.553.497 (3)164
C27—H27B···O4iv0.962.583.136 (3)117
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x+1, y, z; (iii) −x+1, −y+2, −z; (iv) −x, −y+1, −z+1.
Acknowledgements top

The authors thank Professor An–Xin Wu for technical assistance and Dr Meng Xiang–Gao for the data collection.

references
References top

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

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