Literature DB >> 24526994

The chalcone ethyl 2-[4-(2-{2,4-bis-[(eth-oxy-carbon-yl)meth-oxy]benzo-yl}ethen-yl)phen-oxy]acetate.

Xiaofeng Liu1.   

Abstract

In the title mol-ecule, C27H30O10, the benzene rings form a dihedral angle of 14.9 (2)°. The C=C bond is in an E conformation. In the crystal, weak C-H⋯O hydrogen bonds connect the mol-ecules, forming a three-dimensional network.

Entities:  

Year:  2013        PMID: 24526994      PMCID: PMC3914090          DOI: 10.1107/S1600536813033114

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


Related literature

For a related structure, see: Wang et al. (2011 ▶).

Experimental

Crystal data

C27H30O10 M = 514.51 Triclinic, a = 7.8225 (16) Å b = 13.579 (3) Å c = 13.780 (3) Å α = 63.004 (3)° β = 87.157 (4)° γ = 83.377 (4)° V = 1295.6 (5) Å3 Z = 2 Mo Kα radiation μ = 0.10 mm−1 T = 298 K 0.12 × 0.10 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.988, T max = 0.990 16520 measured reflections 4538 independent reflections 4137 reflections with I > 2σ(I) R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.075 wR(F 2) = 0.178 S = 1.20 4538 reflections 337 parameters H-atom parameters constrained Δρmax = 0.39 e Å−3 Δρmin = −0.23 e Å−3 Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶). Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813033114/lh5675sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813033114/lh5675Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S1600536813033114/lh5675Isup3.cml Additional supporting information: crystallographic information; 3D view; checkCIF report
C27H30O10Z = 2
Mr = 514.51F(000) = 544
Triclinic, P1Dx = 1.319 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.8225 (16) ÅCell parameters from 2402 reflections
b = 13.579 (3) Åθ = 0.0–0.0°
c = 13.780 (3) ŵ = 0.10 mm1
α = 63.004 (3)°T = 298 K
β = 87.157 (4)°Block, light yellow
γ = 83.377 (4)°0.12 × 0.10 × 0.10 mm
V = 1295.6 (5) Å3
Bruker APEXII CCD diffractometer4538 independent reflections
Radiation source: fine-focus sealed tube4137 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
φ and ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −7→9
Tmin = 0.988, Tmax = 0.990k = −16→16
16520 measured reflectionsl = −16→16
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.075Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.178H-atom parameters constrained
S = 1.20w = 1/[σ2(Fo2) + (0.0569P)2 + 1.0739P] where P = (Fo2 + 2Fc2)/3
4538 reflections(Δ/σ)max = 0.001
337 parametersΔρmax = 0.39 e Å3
0 restraintsΔρmin = −0.23 e Å3
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
C10.7304 (4)0.4831 (2)0.6468 (2)0.0502 (7)
C20.7010 (4)0.5453 (2)0.7028 (2)0.0549 (8)
H20.71000.62130.66700.066*
C30.6586 (4)0.4962 (2)0.8106 (2)0.0532 (8)
H30.63870.53970.84710.064*
C40.6444 (4)0.3821 (2)0.8675 (2)0.0456 (7)
C50.6802 (4)0.3199 (2)0.8103 (2)0.0525 (7)
H50.67650.24340.84670.063*
C60.7211 (5)0.3687 (2)0.7015 (3)0.0570 (8)
H60.74230.32580.66460.068*
C70.5925 (4)0.3344 (2)0.9813 (2)0.0478 (7)
H70.57900.38291.01240.057*
C80.5619 (4)0.2298 (2)1.0465 (2)0.0467 (7)
H80.57510.17761.01970.056*
C90.5081 (4)0.1960 (2)1.1589 (2)0.0475 (7)
C100.4790 (4)0.0787 (2)1.2360 (2)0.0415 (6)
C110.3962 (4)0.0624 (2)1.3330 (2)0.0459 (7)
H110.35630.12461.34250.055*
C120.3700 (4)−0.0400 (2)1.4151 (2)0.0485 (7)
H120.3136−0.04701.47860.058*
C130.4293 (4)−0.1333 (2)1.4016 (2)0.0435 (6)
C140.5085 (4)−0.1219 (2)1.3063 (2)0.0463 (7)
H140.5449−0.18481.29700.056*
C150.5343 (4)−0.0178 (2)1.2239 (2)0.0432 (6)
C160.7769 (5)0.4821 (2)0.4757 (2)0.0587 (8)
H16A0.67040.44900.48330.070*
H16B0.87090.42300.50060.070*
C170.8034 (4)0.5619 (2)0.3588 (2)0.0517 (7)
C180.8388 (5)0.5709 (3)0.1834 (2)0.0623 (9)
H18A0.94520.60530.16950.075*
H18B0.74450.62870.15140.075*
C190.8467 (6)0.4911 (3)0.1360 (3)0.0855 (12)
H19A0.94020.43420.16870.128*
H19B0.86440.53000.05890.128*
H19C0.74050.45790.15010.128*
C200.3347 (4)−0.2565 (3)1.5781 (2)0.0563 (8)
H20A0.3860−0.21341.60680.068*
H20B0.3559−0.33431.63030.068*
C210.1446 (5)−0.2243 (2)1.5680 (2)0.0547 (8)
C22−0.0998 (5)−0.1807 (3)1.4570 (4)0.0775 (11)
H22A−0.1640−0.19621.52350.093*
H22B−0.1500−0.21591.41940.093*
C23−0.1101 (6)−0.0602 (3)1.3875 (4)0.0955 (14)
H23A−0.0536−0.02621.42310.143*
H23B−0.2287−0.03001.37480.143*
H23C−0.0548−0.04551.31920.143*
C240.6858 (5)−0.0966 (2)1.1165 (3)0.0592 (8)
H24A0.5934−0.13921.11800.071*
H24B0.7663−0.14411.17470.071*
C250.7749 (4)−0.0555 (3)1.0089 (2)0.0522 (7)
C260.9388 (5)−0.1206 (3)0.8969 (3)0.0672 (9)
H26A1.0458−0.09240.89980.081*
H26B0.8735−0.06520.83400.081*
C270.9746 (5)−0.2257 (3)0.8881 (3)0.0744 (10)
H27A1.0383−0.28020.95090.112*
H27B1.0409−0.21280.82360.112*
H27C0.8680−0.25230.88390.112*
O10.4841 (4)0.26559 (18)1.19312 (19)0.0826 (9)
O20.7698 (3)0.54015 (16)0.53900 (17)0.0655 (7)
O30.8152 (4)0.65850 (18)0.32433 (19)0.0776 (8)
O40.8129 (3)0.50759 (17)0.29960 (16)0.0608 (6)
O50.4174 (3)−0.24062 (16)1.47859 (16)0.0541 (5)
O60.0654 (4)−0.2021 (3)1.6330 (2)0.0971 (10)
O70.0789 (3)−0.22501 (18)1.48300 (19)0.0618 (6)
O80.6192 (3)−0.00224 (16)1.13008 (17)0.0653 (7)
O90.7865 (4)0.03736 (19)0.9457 (2)0.0800 (8)
O100.8417 (3)−0.14310 (17)0.99470 (18)0.0649 (6)
U11U22U33U12U13U23
C10.0668 (19)0.0382 (15)0.0429 (15)−0.0079 (13)0.0095 (13)−0.0164 (13)
C20.084 (2)0.0296 (14)0.0496 (17)−0.0093 (14)0.0116 (15)−0.0164 (13)
C30.077 (2)0.0357 (15)0.0514 (17)−0.0058 (14)0.0095 (15)−0.0243 (14)
C40.0550 (17)0.0351 (14)0.0448 (15)−0.0043 (12)0.0028 (13)−0.0167 (12)
C50.077 (2)0.0294 (14)0.0467 (16)−0.0097 (13)0.0093 (14)−0.0137 (12)
C60.087 (2)0.0378 (15)0.0510 (17)−0.0099 (15)0.0129 (16)−0.0245 (14)
C70.0630 (18)0.0347 (14)0.0464 (16)−0.0035 (13)0.0047 (13)−0.0198 (13)
C80.0611 (18)0.0381 (15)0.0424 (15)−0.0054 (13)0.0022 (13)−0.0195 (12)
C90.0638 (19)0.0367 (14)0.0436 (15)−0.0035 (13)0.0021 (13)−0.0202 (13)
C100.0482 (16)0.0381 (14)0.0398 (14)−0.0039 (11)0.0011 (12)−0.0191 (12)
C110.0592 (18)0.0397 (15)0.0457 (15)−0.0066 (13)0.0067 (13)−0.0257 (13)
C120.0607 (18)0.0477 (16)0.0422 (15)−0.0140 (13)0.0145 (13)−0.0242 (13)
C130.0474 (16)0.0383 (14)0.0421 (15)−0.0092 (12)0.0025 (12)−0.0150 (12)
C140.0580 (18)0.0355 (14)0.0486 (16)−0.0049 (12)0.0045 (13)−0.0222 (13)
C150.0545 (17)0.0392 (14)0.0379 (14)−0.0053 (12)0.0060 (12)−0.0196 (12)
C160.088 (2)0.0410 (16)0.0473 (17)−0.0109 (15)0.0127 (16)−0.0206 (14)
C170.067 (2)0.0381 (16)0.0475 (16)−0.0028 (13)0.0083 (14)−0.0183 (13)
C180.085 (2)0.0570 (19)0.0402 (16)−0.0134 (17)0.0100 (15)−0.0179 (15)
C190.126 (4)0.080 (3)0.057 (2)−0.022 (2)0.017 (2)−0.037 (2)
C200.077 (2)0.0471 (17)0.0390 (15)−0.0150 (15)0.0043 (15)−0.0130 (13)
C210.079 (2)0.0411 (16)0.0405 (16)−0.0178 (15)0.0179 (15)−0.0143 (13)
C220.066 (2)0.069 (2)0.105 (3)−0.0102 (18)−0.001 (2)−0.045 (2)
C230.076 (3)0.072 (3)0.122 (4)−0.001 (2)−0.025 (3)−0.028 (3)
C240.086 (2)0.0410 (16)0.0536 (18)−0.0068 (15)0.0161 (16)−0.0254 (14)
C250.070 (2)0.0463 (17)0.0440 (16)−0.0119 (14)0.0091 (14)−0.0231 (14)
C260.071 (2)0.081 (2)0.063 (2)−0.0145 (18)0.0210 (17)−0.0441 (19)
C270.080 (3)0.085 (3)0.071 (2)0.000 (2)0.0112 (19)−0.049 (2)
O10.149 (3)0.0424 (12)0.0593 (14)−0.0150 (14)0.0280 (15)−0.0274 (11)
O20.1146 (19)0.0361 (11)0.0445 (12)−0.0161 (11)0.0222 (12)−0.0174 (9)
O30.133 (2)0.0401 (13)0.0555 (14)−0.0114 (13)0.0162 (14)−0.0190 (11)
O40.0943 (17)0.0451 (12)0.0437 (11)−0.0165 (11)0.0133 (11)−0.0197 (10)
O50.0667 (14)0.0383 (11)0.0483 (12)−0.0082 (9)0.0106 (10)−0.0121 (9)
O60.114 (2)0.114 (2)0.0670 (17)−0.0088 (18)0.0327 (16)−0.0479 (17)
O70.0630 (14)0.0582 (13)0.0735 (15)−0.0026 (11)−0.0009 (11)−0.0387 (12)
O80.1049 (18)0.0377 (11)0.0509 (12)−0.0062 (11)0.0263 (12)−0.0208 (10)
O90.124 (2)0.0459 (14)0.0626 (15)−0.0082 (13)0.0233 (15)−0.0203 (12)
O100.0907 (17)0.0486 (12)0.0585 (13)−0.0094 (11)0.0247 (12)−0.0288 (11)
C1—O21.366 (3)C17—O41.319 (4)
C1—C21.375 (4)C18—O41.450 (4)
C1—C61.394 (4)C18—C191.492 (5)
C2—C31.365 (4)C18—H18A0.9700
C2—H20.9300C18—H18B0.9700
C3—C41.399 (4)C19—H19A0.9600
C3—H30.9300C19—H19B0.9600
C4—C51.393 (4)C19—H19C0.9600
C4—C71.455 (4)C20—O51.422 (4)
C5—C61.375 (4)C20—C211.496 (5)
C5—H50.9300C20—H20A0.9700
C6—H60.9300C20—H20B0.9700
C7—C81.335 (4)C21—O61.193 (4)
C7—H70.9300C21—O71.307 (4)
C8—C91.457 (4)C22—O71.451 (4)
C8—H80.9300C22—C231.468 (5)
C9—O11.227 (3)C22—H22A0.9700
C9—C101.497 (4)C22—H22B0.9700
C10—C111.389 (4)C23—H23A0.9600
C10—C151.412 (4)C23—H23B0.9600
C11—C121.368 (4)C23—H23C0.9600
C11—H110.9300C24—O81.415 (3)
C12—C131.387 (4)C24—C251.494 (4)
C12—H120.9300C24—H24A0.9700
C13—O51.370 (3)C24—H24B0.9700
C13—C141.375 (4)C25—O91.174 (4)
C14—C151.384 (4)C25—O101.335 (4)
C14—H140.9300C26—O101.437 (4)
C15—O81.363 (3)C26—C271.481 (5)
C16—O21.412 (3)C26—H26A0.9700
C16—C171.499 (4)C26—H26B0.9700
C16—H16A0.9700C27—H27A0.9600
C16—H16B0.9700C27—H27B0.9600
C17—O31.189 (3)C27—H27C0.9600
O2—C1—C2116.0 (2)O4—C18—H18B110.3
O2—C1—C6124.5 (3)C19—C18—H18B110.3
C2—C1—C6119.5 (3)H18A—C18—H18B108.6
C3—C2—C1120.5 (3)C18—C19—H19A109.5
C3—C2—H2119.8C18—C19—H19B109.5
C1—C2—H2119.8H19A—C19—H19B109.5
C2—C3—C4121.5 (3)C18—C19—H19C109.5
C2—C3—H3119.2H19A—C19—H19C109.5
C4—C3—H3119.2H19B—C19—H19C109.5
C5—C4—C3117.1 (3)O5—C20—C21114.2 (3)
C5—C4—C7123.4 (2)O5—C20—H20A108.7
C3—C4—C7119.5 (2)C21—C20—H20A108.7
C6—C5—C4121.7 (3)O5—C20—H20B108.7
C6—C5—H5119.1C21—C20—H20B108.7
C4—C5—H5119.1H20A—C20—H20B107.6
C5—C6—C1119.6 (3)O6—C21—O7125.4 (4)
C5—C6—H6120.2O6—C21—C20121.9 (3)
C1—C6—H6120.2O7—C21—C20112.7 (3)
C8—C7—C4128.1 (3)O7—C22—C23109.5 (3)
C8—C7—H7116.0O7—C22—H22A109.8
C4—C7—H7116.0C23—C22—H22A109.8
C7—C8—C9121.0 (3)O7—C22—H22B109.8
C7—C8—H8119.5C23—C22—H22B109.8
C9—C8—H8119.5H22A—C22—H22B108.2
O1—C9—C8119.6 (3)C22—C23—H23A109.5
O1—C9—C10117.6 (3)C22—C23—H23B109.5
C8—C9—C10122.8 (2)H23A—C23—H23B109.5
C11—C10—C15116.3 (2)C22—C23—H23C109.5
C11—C10—C9116.4 (2)H23A—C23—H23C109.5
C15—C10—C9127.2 (2)H23B—C23—H23C109.5
C12—C11—C10123.8 (3)O8—C24—C25107.2 (2)
C12—C11—H11118.1O8—C24—H24A110.3
C10—C11—H11118.1C25—C24—H24A110.3
C11—C12—C13118.5 (3)O8—C24—H24B110.3
C11—C12—H12120.7C25—C24—H24B110.3
C13—C12—H12120.7H24A—C24—H24B108.5
O5—C13—C14115.1 (2)O9—C25—O10124.3 (3)
O5—C13—C12124.6 (2)O9—C25—C24127.2 (3)
C14—C13—C12120.2 (2)O10—C25—C24108.5 (2)
C13—C14—C15120.6 (2)O10—C26—C27108.1 (3)
C13—C14—H14119.7O10—C26—H26A110.1
C15—C14—H14119.7C27—C26—H26A110.1
O8—C15—C14122.9 (2)O10—C26—H26B110.1
O8—C15—C10116.4 (2)C27—C26—H26B110.1
C14—C15—C10120.6 (2)H26A—C26—H26B108.4
O2—C16—C17108.9 (2)C26—C27—H27A109.5
O2—C16—H16A109.9C26—C27—H27B109.5
C17—C16—H16A109.9H27A—C27—H27B109.5
O2—C16—H16B109.9C26—C27—H27C109.5
C17—C16—H16B109.9H27A—C27—H27C109.5
H16A—C16—H16B108.3H27B—C27—H27C109.5
O3—C17—O4125.1 (3)C1—O2—C16117.3 (2)
O3—C17—C16125.8 (3)C17—O4—C18117.4 (2)
O4—C17—C16109.1 (2)C13—O5—C20117.2 (2)
O4—C18—C19106.9 (3)C21—O7—C22117.3 (3)
O4—C18—H18A110.3C15—O8—C24118.7 (2)
C19—C18—H18A110.3C25—O10—C26116.9 (3)
O2—C1—C2—C3179.2 (3)C11—C10—C15—O8−178.5 (3)
C6—C1—C2—C3−1.7 (5)C9—C10—C15—O8−2.1 (4)
C1—C2—C3—C40.3 (5)C11—C10—C15—C14−1.1 (4)
C2—C3—C4—C51.8 (5)C9—C10—C15—C14175.2 (3)
C2—C3—C4—C7−177.7 (3)O2—C16—C17—O3−0.6 (5)
C3—C4—C5—C6−2.6 (5)O2—C16—C17—O4179.0 (3)
C7—C4—C5—C6176.9 (3)O5—C20—C21—O6−158.1 (3)
C4—C5—C6—C11.3 (5)O5—C20—C21—O722.8 (4)
O2—C1—C6—C5180.0 (3)O8—C24—C25—O9−1.1 (5)
C2—C1—C6—C50.9 (5)O8—C24—C25—O10179.0 (3)
C5—C4—C7—C8−3.9 (5)C2—C1—O2—C16−171.3 (3)
C3—C4—C7—C8175.5 (3)C6—C1—O2—C169.6 (5)
C4—C7—C8—C9−179.1 (3)C17—C16—O2—C1174.2 (3)
C7—C8—C9—O12.8 (5)O3—C17—O4—C18−0.3 (5)
C7—C8—C9—C10−177.6 (3)C16—C17—O4—C18−179.9 (3)
O1—C9—C10—C1111.9 (4)C19—C18—O4—C17179.4 (3)
C8—C9—C10—C11−167.7 (3)C14—C13—O5—C20−179.2 (3)
O1—C9—C10—C15−164.5 (3)C12—C13—O5—C201.5 (4)
C8—C9—C10—C1515.9 (5)C21—C20—O5—C1370.3 (3)
C15—C10—C11—C121.3 (4)O6—C21—O7—C229.1 (5)
C9—C10—C11—C12−175.5 (3)C20—C21—O7—C22−171.9 (3)
C10—C11—C12—C130.1 (5)C23—C22—O7—C2187.1 (4)
C11—C12—C13—O5177.5 (3)C14—C15—O8—C24−0.8 (5)
C11—C12—C13—C14−1.7 (4)C10—C15—O8—C24176.5 (3)
O5—C13—C14—C15−177.4 (3)C25—C24—O8—C15−178.7 (3)
C12—C13—C14—C151.9 (4)O9—C25—O10—C262.3 (5)
C13—C14—C15—O8176.8 (3)C24—C25—O10—C26−177.7 (3)
C13—C14—C15—C10−0.4 (4)C27—C26—O10—C25−170.4 (3)
D—H···AD—HH···AD···AD—H···A
C3—H3···O1i0.932.523.276 (4)138
C16—H16B···O7ii0.972.583.337 (4)135
C20—H20B···O4ii0.972.603.360 (4)136
C24—H24B···O3iii0.972.533.339 (4)141
C27—H27B···O6iv0.962.563.426 (4)150
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A DA D—H⋯A
C3—H3⋯O1i 0.932.523.276 (4)138
C16—H16B⋯O7ii 0.972.583.337 (4)135
C20—H20B⋯O4ii 0.972.603.360 (4)136
C24—H24B⋯O3iii 0.972.533.339 (4)141
C27—H27B⋯O6iv 0.962.563.426 (4)150

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

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