Literature DB >> 21578453

3-(4-Acetoxy-phen-yl)-4-oxo-4H-1-benzopyran-5,7-diyl diacetate.

Huan-Qiu Li1, Yin Luo, Dong-Dong Li, Hai-Liang Zhu.   

Abstract

In the title mol-ecule, C(21)H(16)O(8), the dihedral angle between the ring systems is 58.5 (1)°. In the crystal, C-H⋯O inter-actions help to establish the packing.

Entities:  

Year:  2009        PMID： 21578453      PMCID： PMC2971439          DOI： 10.1107/S1600536809043670

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For background to genistein derivatives, see: Li et al. (2006 ▶). For reference structural data, see: Allen et al. (1987 ▶). For related literature, see: Liu & Zhu (2005 ▶).

Experimental

Crystal data

C21H16O8 M = 396.34 Triclinic, a = 7.6144 (14) Å b = 10.6755 (19) Å c = 12.533 (2) Å α = 72.489 (3)° β = 73.848 (3)° γ = 74.762 (3)° V = 915.2 (3) Å3 Z = 2 Mo Kα radiation μ = 0.11 mm−1 T = 298 K 0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.967, T max = 0.989 4847 measured reflections 3043 independent reflections 1968 reflections with I > 2σ(I) R int = 0.025 200 standard reflections every 3 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.046 wR(F 2) = 0.113 S = 0.96 3043 reflections 265 parameters H-atom parameters constrained Δρmax = 0.17 e Å−3 Δρmin = −0.17 e Å−3 Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809043670/hb5164sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043670/hb5164Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C21H16O8Z = 2
Mr = 396.34F(000) = 412
Triclinic, P1Dx = 1.438 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.6144 (14) ÅCell parameters from 25 reflections
b = 10.6755 (19) Åθ = 9–12°
c = 12.533 (2) ŵ = 0.11 mm−1
α = 72.489 (3)°T = 298 K
β = 73.848 (3)°Block, colourless
γ = 74.762 (3)°0.30 × 0.20 × 0.10 mm
V = 915.2 (3) Å3
Enraf–Nonius CAD-4 diffractometer1968 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.025
graphiteθmax = 25.0°, θmin = 1.8°
ω/2θ scansh = −8→9
Absorption correction: ψ scan (North et al., 1968)k = −12→11
Tmin = 0.967, Tmax = 0.989l = −14→14
4847 measured reflections200 standard reflections every 3 reflections
3043 independent reflections intensity decay: 1%
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H-atom parameters constrained
S = 0.96w = 1/[σ2(Fo2) + (0.0486P)2] where P = (Fo2 + 2Fc2)/3
3043 reflections(Δ/σ)max = 0.008
265 parametersΔρmax = 0.17 e Å−3
0 restraintsΔρmin = −0.17 e Å−3
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.
xyzUiso*/Ueq
C10.2549 (3)−0.0952 (3)0.18430 (19)0.0501 (6)
H10.2405−0.18330.21860.060*
C20.2866 (3)−0.0287 (2)0.24896 (17)0.0396 (6)
C30.3137 (3)0.1090 (2)0.19959 (17)0.0384 (6)
C40.2951 (3)0.2985 (2)0.01826 (17)0.0359 (5)
C50.2684 (3)0.3459 (2)−0.09068 (17)0.0400 (6)
H50.27050.4350−0.12890.048*
C60.2379 (3)0.2591 (2)−0.14434 (17)0.0396 (6)
C70.2302 (3)0.1288 (2)−0.08973 (17)0.0419 (6)
H70.20950.0718−0.12630.050*
C80.2545 (3)0.0838 (2)0.02250 (17)0.0397 (6)
C90.2890 (3)0.1646 (2)0.08047 (17)0.0353 (5)
C100.2867 (3)−0.0925 (2)0.37225 (18)0.0401 (6)
C110.1331 (3)−0.1409 (3)0.44474 (19)0.0489 (6)
H110.0303−0.13460.41580.059*
C120.1296 (3)−0.1986 (3)0.55972 (19)0.0494 (6)
H120.0259−0.23150.60810.059*
C130.2823 (3)−0.2065 (2)0.60117 (18)0.0433 (6)
C140.4364 (3)−0.1589 (2)0.53217 (18)0.0463 (6)
H140.5384−0.16550.56200.056*
C150.4382 (3)−0.1008 (2)0.41701 (19)0.0468 (6)
H150.5417−0.06710.36940.056*
C160.2072 (3)0.4303 (2)0.15330 (19)0.0408 (6)
C170.2872 (4)0.5041 (3)0.2056 (2)0.0600 (7)
H17A0.18810.55420.25180.090*
H17B0.35700.56430.14620.090*
H17C0.36800.44150.25270.090*
C180.3122 (4)0.3839 (3)−0.33891 (19)0.0513 (7)
C190.2309 (4)0.4375 (3)−0.4425 (2)0.0703 (8)
H19A0.32180.4743−0.50660.105*
H19B0.12320.5063−0.42910.105*
H19C0.19530.3665−0.45880.105*
C200.2196 (3)−0.1878 (3)0.79073 (19)0.0423 (6)
C210.2206 (3)−0.2675 (3)0.91124 (17)0.0501 (7)
H21A0.1991−0.20790.95970.075*
H21B0.3393−0.32670.91410.075*
H21C0.1240−0.31910.93730.075*
O10.2418 (2)−0.04736 (16)0.07344 (12)0.0517 (5)
O20.3515 (2)0.17371 (16)0.25336 (13)0.0543 (5)
O30.3377 (2)0.38639 (15)0.06600 (12)0.0400 (4)
O40.1996 (2)0.30585 (17)−0.25361 (12)0.0496 (4)
O50.2817 (2)−0.26831 (16)0.71821 (12)0.0491 (4)
O60.0523 (2)0.41095 (18)0.17983 (14)0.0587 (5)
O70.4524 (3)0.4012 (2)−0.32773 (14)0.0704 (6)
O80.1702 (2)−0.06907 (19)0.76094 (14)0.0620 (5)
U11U22U33U12U13U23
C10.0721 (17)0.0365 (15)0.0389 (14)−0.0123 (13)−0.0165 (12)0.0003 (11)
C20.0428 (13)0.0343 (14)0.0396 (13)−0.0042 (11)−0.0109 (11)−0.0070 (11)
C30.0342 (12)0.0426 (15)0.0383 (12)−0.0040 (11)−0.0100 (10)−0.0108 (11)
C40.0325 (12)0.0384 (14)0.0384 (13)−0.0076 (10)−0.0090 (10)−0.0100 (10)
C50.0410 (13)0.0381 (14)0.0386 (13)−0.0093 (11)−0.0085 (10)−0.0049 (11)
C60.0407 (13)0.0469 (16)0.0314 (12)−0.0075 (11)−0.0085 (10)−0.0101 (11)
C70.0486 (14)0.0438 (16)0.0386 (13)−0.0120 (12)−0.0096 (11)−0.0152 (11)
C80.0431 (14)0.0363 (15)0.0372 (13)−0.0069 (11)−0.0075 (10)−0.0073 (10)
C90.0329 (12)0.0344 (14)0.0372 (12)−0.0050 (10)−0.0075 (10)−0.0082 (10)
C100.0490 (14)0.0318 (14)0.0376 (13)−0.0028 (11)−0.0114 (11)−0.0083 (10)
C110.0512 (15)0.0510 (17)0.0447 (14)−0.0123 (13)−0.0168 (12)−0.0041 (12)
C120.0512 (15)0.0505 (17)0.0421 (14)−0.0154 (12)−0.0050 (12)−0.0049 (12)
C130.0594 (16)0.0364 (15)0.0332 (12)−0.0075 (12)−0.0129 (11)−0.0064 (10)
C140.0513 (15)0.0454 (16)0.0429 (14)−0.0091 (12)−0.0181 (12)−0.0049 (12)
C150.0486 (15)0.0447 (16)0.0452 (14)−0.0128 (12)−0.0095 (12)−0.0058 (12)
C160.0457 (15)0.0366 (15)0.0408 (13)−0.0067 (11)−0.0142 (11)−0.0071 (11)
C170.0672 (18)0.0626 (19)0.0603 (16)−0.0176 (15)−0.0137 (14)−0.0256 (14)
C180.0628 (18)0.0495 (17)0.0384 (14)−0.0102 (14)−0.0084 (13)−0.0095 (12)
C190.088 (2)0.071 (2)0.0444 (15)−0.0077 (16)−0.0230 (15)−0.0021 (14)
C200.0391 (13)0.0459 (17)0.0446 (14)−0.0077 (12)−0.0108 (11)−0.0139 (12)
C210.0490 (14)0.0631 (18)0.0385 (13)−0.0107 (13)−0.0128 (11)−0.0100 (12)
O10.0822 (12)0.0373 (10)0.0410 (9)−0.0177 (9)−0.0192 (8)−0.0071 (7)
O20.0783 (12)0.0447 (11)0.0495 (10)−0.0160 (9)−0.0333 (9)−0.0042 (8)
O30.0431 (9)0.0406 (10)0.0403 (8)−0.0140 (7)−0.0096 (7)−0.0102 (7)
O40.0595 (10)0.0558 (11)0.0355 (9)−0.0138 (9)−0.0180 (8)−0.0050 (8)
O50.0678 (11)0.0410 (10)0.0363 (9)−0.0091 (8)−0.0147 (8)−0.0043 (8)
O60.0420 (10)0.0676 (13)0.0711 (12)−0.0153 (9)−0.0061 (9)−0.0254 (10)
O70.0757 (13)0.0925 (16)0.0483 (11)−0.0369 (12)−0.0087 (10)−0.0113 (10)
O80.0805 (13)0.0464 (12)0.0555 (11)0.0031 (10)−0.0225 (10)−0.0136 (9)
C1—C21.328 (3)C13—C141.366 (3)
C1—O11.351 (2)C13—O51.415 (2)
C1—H10.9300C14—C151.387 (3)
C2—C31.459 (3)C14—H140.9300
C2—C101.490 (3)C15—H150.9300
C3—O21.227 (2)C16—O61.189 (2)
C3—C91.477 (3)C16—O31.365 (3)
C4—C51.359 (3)C16—C171.485 (3)
C4—O31.396 (2)C17—H17A0.9600
C4—C91.414 (3)C17—H17B0.9600
C5—C61.392 (3)C17—H17C0.9600
C5—H50.9300C18—O71.182 (3)
C6—C71.362 (3)C18—O41.379 (3)
C6—O41.394 (2)C18—C191.487 (3)
C7—C81.391 (3)C19—H19A0.9600
C7—H70.9300C19—H19B0.9600
C8—O11.370 (3)C19—H19C0.9600
C8—C91.394 (3)C20—O81.196 (3)
C10—C111.380 (3)C20—O51.344 (3)
C10—C151.389 (3)C20—C211.495 (3)
C11—C121.382 (3)C21—H21A0.9600
C11—H110.9300C21—H21B0.9600
C12—C131.374 (3)C21—H21C0.9600
C12—H120.9300
C2—C1—O1126.3 (2)C12—C13—O5119.0 (2)
C2—C1—H1116.9C13—C14—C15118.9 (2)
O1—C1—H1116.9C13—C14—H14120.5
C1—C2—C3119.5 (2)C15—C14—H14120.5
C1—C2—C10120.2 (2)C14—C15—C10120.5 (2)
C3—C2—C10120.22 (19)C14—C15—H15119.7
O2—C3—C2122.63 (19)C10—C15—H15119.7
O2—C3—C9122.9 (2)O6—C16—O3122.7 (2)
C2—C3—C9114.48 (19)O6—C16—C17126.9 (2)
C5—C4—O3117.23 (19)O3—C16—C17110.41 (19)
C5—C4—C9122.3 (2)C16—C17—H17A109.5
O3—C4—C9120.37 (17)C16—C17—H17B109.5
C4—C5—C6119.1 (2)H17A—C17—H17B109.5
C4—C5—H5120.4C16—C17—H17C109.5
C6—C5—H5120.4H17A—C17—H17C109.5
C7—C6—C5121.76 (19)H17B—C17—H17C109.5
C7—C6—O4117.3 (2)O7—C18—O4123.0 (2)
C5—C6—O4120.7 (2)O7—C18—C19127.3 (2)
C6—C7—C8117.9 (2)O4—C18—C19109.8 (2)
C6—C7—H7121.1C18—C19—H19A109.5
C8—C7—H7121.1C18—C19—H19B109.5
O1—C8—C7115.1 (2)H19A—C19—H19B109.5
O1—C8—C9121.63 (18)C18—C19—H19C109.5
C7—C8—C9123.3 (2)H19A—C19—H19C109.5
C8—C9—C4115.59 (18)H19B—C19—H19C109.5
C8—C9—C3120.0 (2)O8—C20—O5123.6 (2)
C4—C9—C3124.43 (19)O8—C20—C21125.8 (2)
C11—C10—C15118.88 (19)O5—C20—C21110.6 (2)
C11—C10—C2120.20 (19)C20—C21—H21A109.5
C15—C10—C2120.9 (2)C20—C21—H21B109.5
C10—C11—C12121.0 (2)H21A—C21—H21B109.5
C10—C11—H11119.5C20—C21—H21C109.5
C12—C11—H11119.5H21A—C21—H21C109.5
C13—C12—C11118.7 (2)H21B—C21—H21C109.5
C13—C12—H12120.7C1—O1—C8117.90 (18)
C11—C12—H12120.7C16—O3—C4117.96 (15)
C14—C13—C12121.9 (2)C18—O4—C6119.08 (18)
C14—C13—O5119.02 (19)C20—O5—C13116.67 (18)
O1—C1—C2—C3−1.0 (4)C1—C2—C10—C15125.7 (3)
O1—C1—C2—C10176.5 (2)C3—C2—C10—C15−56.8 (3)
C1—C2—C3—O2−176.7 (2)C15—C10—C11—C12−0.9 (4)
C10—C2—C3—O25.7 (3)C2—C10—C11—C12−179.1 (2)
C1—C2—C3—C94.2 (3)C10—C11—C12—C130.3 (4)
C10—C2—C3—C9−173.35 (19)C11—C12—C13—C140.1 (4)
O3—C4—C5—C6175.77 (18)C11—C12—C13—O5−178.5 (2)
C9—C4—C5—C6−1.4 (3)C12—C13—C14—C150.2 (4)
C4—C5—C6—C71.4 (3)O5—C13—C14—C15178.7 (2)
C4—C5—C6—O4176.38 (18)C13—C14—C15—C10−0.8 (4)
C5—C6—C7—C8−0.2 (3)C11—C10—C15—C141.1 (4)
O4—C6—C7—C8−175.31 (19)C2—C10—C15—C14179.3 (2)
C6—C7—C8—O1178.82 (19)C2—C1—O1—C8−2.8 (4)
C6—C7—C8—C9−1.1 (3)C7—C8—O1—C1−176.8 (2)
O1—C8—C9—C4−178.87 (18)C9—C8—O1—C13.1 (3)
C7—C8—C9—C41.0 (3)O6—C16—O3—C4−9.9 (3)
O1—C8—C9—C30.3 (3)C17—C16—O3—C4170.81 (18)
C7—C8—C9—C3−179.8 (2)C5—C4—O3—C16111.1 (2)
C5—C4—C9—C80.3 (3)C9—C4—O3—C16−71.6 (2)
O3—C4—C9—C8−176.86 (18)O7—C18—O4—C68.7 (4)
C5—C4—C9—C3−178.8 (2)C19—C18—O4—C6−172.2 (2)
O3—C4—C9—C34.0 (3)C7—C6—O4—C18−136.0 (2)
O2—C3—C9—C8177.1 (2)C5—C6—O4—C1848.8 (3)
C2—C3—C9—C8−3.8 (3)O8—C20—O5—C13−1.6 (3)
O2—C3—C9—C4−3.8 (3)C21—C20—O5—C13177.94 (18)
C2—C3—C9—C4175.25 (19)C14—C13—O5—C2089.1 (3)
C1—C2—C10—C11−56.2 (3)C12—C13—O5—C20−92.3 (3)
C3—C2—C10—C11121.3 (2)
D—H···AD—HH···AD···AD—H···A
C7—H7···O8i0.932.473.396 (3)175
C19—H19A···O7ii0.962.573.523 (3)173
C21—H21B···O3iii0.962.443.328 (3)154
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C7—H7⋯O8i0.932.473.396 (3)175
C19—H19A⋯O7ii0.962.573.523 (3)173
C21—H21B⋯O3iii0.962.443.328 (3)154

Symmetry codes: (i) ; (ii) ; (iii) .

  2 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Synthesis and cytotoxic evaluation of a series of genistein derivatives.

Authors:  Huan-Qiu Li; Hui-Ming Ge; Yun-Xi Chen; Chen Xu; Lei Shi; Hui Ding; Hai-Liang Zhu; Ren-Xiang Tan
Journal:  Chem Biodivers       Date:  2006-04       Impact factor: 2.408
  2 in total

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