organic compounds
E)-3-(4-methoxyphenyl)prop-2-enoyl]phenyl benzoate
of 4-[(2aPG and Research Department of Physics, Queen Mary's College, Chennai-4, Tamilnadu, India, and bDepartment of Chemistry, Madras Christian College, Chennai-59, India
*Correspondence e-mail: guqmc@yahoo.com
In the title compound, C23H18O4, the methoxybenzene ring and attached C=C grouping are disordered over two sets of sites in a 0.823 (5):0.177 (5) ratio. The dihedral angles between the central benzene ring and the pendant phenyl and methoxybenzene ring (major orientation) are 51.21 (1) and 51.6 (1)°, respectively. In the crystal, inversion dimers linked by pairs of C—H⋯O hydrogen bonds generate R22(28) loops.
Keywords: crystal structure; benzoate; hydrogen bonding.
CCDC reference: 1018848
1. Related literature
For background to flavenoids, see: Di Carlo et al. (1999); Rackova et al. (2005); Harborne & Williams (2000). For related structures, see: Moreno-Fuquen et al. (2014); Jasinski et al. (2011); Sathya et al. (2014).
2. Experimental
2.1. Crystal data
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2.3. Refinement
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Data collection: APEX2 (Bruker, 2004); cell 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: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97.
Supporting information
CCDC reference: 1018848
10.1107/S1600536814018303/hb7255sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814018303/hb7255Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814018303/hb7255Isup3.cml
The chalcone derivative is prepared by two steps.
In a 250 mL round-bottomed flask 4-hydroxyacetophenone (0.05 mol) and 4-methoxybenzaldehyde (0.05 mol) were taken to which 120 mL of absolute alcohol was added and stirred at room temperature for a span of 5 minutes. Then 20 mL of 20% sodium hydroxide solution was added and the mixture was stirred for 2 h. The precipitate generated by adding sufficient amount of dilute hydrochloric acid was filtered, washed with water and dried. The crude product was recrystallized twice from absolute alcohol. % of yield: 90.
The second step involves esterification reaction: in a 250 mL round-bottomed flask the chalcone (0.02 mol) was taken in, to which 120 mL of ethyl methyl ketone was added and stirred at room temperature. After a span of 5 minutes, triethylamine (0.04 mol) was added and the mixture was stirred for 15 minutes. Then benzoylchloride (0.02 mol) was added and the reaction mixture was stirred at room temperature for about 2 h. A white precipitate of triethyl ammonium chloride was formed. It was filtered and the filterate was evaporated to get the crude product. The crude product was recrystallized twice from ethyl methyl ketone solution. % of yield: 95.
H atoms were positioned geometrically and treated as riding on their parent atoms, with C—H distance of 0.93–0.96 Å, with Uiso(H)= 1.5 Ueq(c-methyl) and Uiso(H)= 1.2Ueq(C) for other H atom. The phenyl benzoate group of the molecule was refined using a disorder model, with relative occupancies of approximately 82.3% and 17.7%.
Data collection: APEX2 (Bruker, 2004); cell
SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).C23H18O4 | F(000) = 752 |
Mr = 358.37 | Dx = 1.321 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3462 reflections |
a = 20.146 (5) Å | θ = 2.6–25.6° |
b = 14.513 (5) Å | µ = 0.09 mm−1 |
c = 6.187 (5) Å | T = 293 K |
β = 94.828 (5)° | Block, yellow |
V = 1802.5 (16) Å3 | 0.35 × 0.30 × 0.25 mm |
Z = 4 |
Bruker APEXII CCD diffractometer | 3170 independent reflections |
Radiation source: fine-focus sealed tube | 2523 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.045 |
ω and ϕ scan | θmax = 25.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −23→23 |
Tmin = 0.969, Tmax = 0.978 | k = −17→17 |
17041 measured reflections | l = −7→7 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.056 | H-atom parameters constrained |
wR(F2) = 0.195 | w = 1/[σ2(Fo2) + (0.0812P)2 + 1.0118P] where P = (Fo2 + 2Fc2)/3 |
S = 1.11 | (Δ/σ)max = 0.001 |
3170 reflections | Δρmax = 0.21 e Å−3 |
320 parameters | Δρmin = −0.17 e Å−3 |
334 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0043 (17) |
C23H18O4 | V = 1802.5 (16) Å3 |
Mr = 358.37 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 20.146 (5) Å | µ = 0.09 mm−1 |
b = 14.513 (5) Å | T = 293 K |
c = 6.187 (5) Å | 0.35 × 0.30 × 0.25 mm |
β = 94.828 (5)° |
Bruker APEXII CCD diffractometer | 3170 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 2523 reflections with I > 2σ(I) |
Tmin = 0.969, Tmax = 0.978 | Rint = 0.045 |
17041 measured reflections |
R[F2 > 2σ(F2)] = 0.056 | 334 restraints |
wR(F2) = 0.195 | H-atom parameters constrained |
S = 1.11 | Δρmax = 0.21 e Å−3 |
3170 reflections | Δρmin = −0.17 e Å−3 |
320 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.89122 (16) | 0.6485 (2) | 0.0011 (5) | 0.0631 (8) | |
H1 | 0.8506 | 0.6659 | −0.0694 | 0.076* | |
C2 | 0.94911 (18) | 0.6612 (2) | −0.0966 (5) | 0.0746 (9) | |
H2 | 0.9474 | 0.6882 | −0.2332 | 0.090* | |
C3 | 1.00923 (18) | 0.6348 (2) | 0.0027 (6) | 0.0789 (10) | |
H3 | 1.0480 | 0.6438 | −0.0660 | 0.095* | |
C4 | 1.01200 (17) | 0.5948 (3) | 0.2058 (6) | 0.0773 (9) | |
H4 | 1.0527 | 0.5760 | 0.2737 | 0.093* | |
C5 | 0.95459 (15) | 0.5829 (2) | 0.3071 (5) | 0.0665 (8) | |
H5 | 0.9566 | 0.5568 | 0.4448 | 0.080* | |
C6 | 0.89386 (13) | 0.60929 (18) | 0.2065 (4) | 0.0514 (7) | |
C7 | 0.83392 (14) | 0.59524 (18) | 0.3243 (5) | 0.0540 (7) | |
C8 | 0.71707 (13) | 0.62650 (18) | 0.3021 (4) | 0.0515 (7) | |
C9 | 0.70646 (14) | 0.66395 (18) | 0.5013 (5) | 0.0555 (7) | |
H9 | 0.7417 | 0.6891 | 0.5888 | 0.067* | |
C10 | 0.64306 (14) | 0.66356 (18) | 0.5684 (5) | 0.0555 (7) | |
H10 | 0.6356 | 0.6871 | 0.7040 | 0.067* | |
C11 | 0.59009 (14) | 0.62820 (18) | 0.4352 (5) | 0.0575 (7) | |
C12 | 0.60283 (15) | 0.5913 (2) | 0.2357 (5) | 0.0687 (9) | |
H12 | 0.5679 | 0.5673 | 0.1449 | 0.082* | |
C13 | 0.66607 (15) | 0.5899 (2) | 0.1713 (5) | 0.0625 (8) | |
H13 | 0.6742 | 0.5641 | 0.0385 | 0.075* | |
O1 | 0.83266 (11) | 0.55704 (16) | 0.4953 (3) | 0.0757 (7) | |
O2 | 0.77922 (9) | 0.63206 (14) | 0.2161 (3) | 0.0613 (6) | |
C14 | 0.5205 (2) | 0.6314 (5) | 0.4965 (9) | 0.0649 (15) | 0.823 (5) |
C15 | 0.4662 (2) | 0.6328 (4) | 0.3246 (11) | 0.0682 (15) | 0.823 (5) |
H15 | 0.4749 | 0.6488 | 0.1842 | 0.082* | 0.823 (5) |
C16 | 0.40600 (19) | 0.6119 (2) | 0.3661 (7) | 0.0610 (10) | 0.823 (5) |
H16 | 0.3996 | 0.5946 | 0.5076 | 0.073* | 0.823 (5) |
O4 | 0.16821 (8) | 0.61934 (12) | −0.1635 (3) | 0.0731 (16) | 0.823 (5) |
C20 | 0.22860 (8) | 0.61731 (12) | −0.0591 (3) | 0.0506 (9) | 0.823 (5) |
C21 | 0.23058 (8) | 0.57341 (12) | 0.1410 (3) | 0.0521 (10) | 0.823 (5) |
H21 | 0.1925 | 0.5454 | 0.1853 | 0.063* | 0.823 (5) |
C22 | 0.28953 (8) | 0.57131 (12) | 0.2749 (3) | 0.0545 (10) | 0.823 (5) |
H22 | 0.2909 | 0.5419 | 0.4088 | 0.065* | 0.823 (5) |
C17 | 0.34650 (8) | 0.61310 (12) | 0.2087 (3) | 0.0517 (11) | 0.823 (5) |
C18 | 0.34452 (8) | 0.65700 (12) | 0.0085 (3) | 0.0569 (10) | 0.823 (5) |
H18 | 0.3826 | 0.6850 | −0.0358 | 0.068* | 0.823 (5) |
C19 | 0.28557 (8) | 0.65910 (12) | −0.1254 (3) | 0.0567 (11) | 0.823 (5) |
H19 | 0.2842 | 0.6885 | −0.2593 | 0.068* | 0.823 (5) |
O3 | 0.5124 (2) | 0.6334 (5) | 0.6900 (8) | 0.0909 (14) | 0.823 (5) |
C23 | 0.1593 (5) | 0.6736 (9) | −0.3550 (11) | 0.073 (2) | 0.823 (5) |
H23A | 0.1704 | 0.7365 | −0.3209 | 0.109* | 0.823 (5) |
H23B | 0.1137 | 0.6699 | −0.4135 | 0.109* | 0.823 (5) |
H23C | 0.1878 | 0.6509 | −0.4599 | 0.109* | 0.823 (5) |
C14' | 0.5326 (7) | 0.624 (3) | 0.575 (3) | 0.063 (6) | 0.177 (5) |
C15' | 0.4574 (6) | 0.6085 (10) | 0.476 (2) | 0.038 (3) | 0.177 (5) |
H15' | 0.4262 | 0.5844 | 0.5633 | 0.046* | 0.177 (5) |
C16' | 0.4385 (10) | 0.6305 (14) | 0.263 (3) | 0.042 (3) | 0.177 (5) |
H16' | 0.4730 | 0.6518 | 0.1852 | 0.050* | 0.177 (5) |
O4' | 0.1697 (4) | 0.6196 (6) | −0.1703 (13) | 0.060 (6) | 0.177 (5) |
C20' | 0.2427 (4) | 0.6185 (6) | −0.0378 (13) | 0.062 (4) | 0.177 (5) |
C21' | 0.2604 (4) | 0.5803 (6) | 0.1649 (13) | 0.050 (4) | 0.177 (5) |
H21' | 0.2283 | 0.5520 | 0.2417 | 0.060* | 0.177 (5) |
C22' | 0.3262 (4) | 0.5842 (6) | 0.2528 (13) | 0.045 (4) | 0.177 (5) |
H22' | 0.3380 | 0.5586 | 0.3884 | 0.054* | 0.177 (5) |
C17' | 0.3742 (4) | 0.6264 (6) | 0.1381 (13) | 0.044 (3) | 0.177 (5) |
C18' | 0.3565 (4) | 0.6646 (6) | −0.0646 (13) | 0.069 (4) | 0.177 (5) |
H18' | 0.3887 | 0.6929 | −0.1413 | 0.083* | 0.177 (5) |
C19' | 0.2908 (4) | 0.6607 (6) | −0.1525 (13) | 0.063 (4) | 0.177 (5) |
H19' | 0.2790 | 0.6863 | −0.2881 | 0.076* | 0.177 (5) |
O3' | 0.5304 (9) | 0.628 (2) | 0.774 (2) | 0.076 (5) | 0.177 (5) |
C23' | 0.161 (3) | 0.661 (5) | −0.380 (6) | 0.095 (14) | 0.177 (5) |
H23D | 0.1932 | 0.7093 | −0.3896 | 0.142* | 0.177 (5) |
H23E | 0.1171 | 0.6853 | −0.4042 | 0.142* | 0.177 (5) |
H23F | 0.1680 | 0.6149 | −0.4884 | 0.142* | 0.177 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.072 (2) | 0.0635 (19) | 0.0548 (17) | 0.0032 (14) | 0.0081 (14) | 0.0041 (14) |
C2 | 0.089 (3) | 0.073 (2) | 0.0646 (19) | −0.0015 (17) | 0.0248 (18) | 0.0038 (16) |
C3 | 0.073 (2) | 0.080 (2) | 0.088 (2) | −0.0085 (18) | 0.0321 (19) | −0.0092 (19) |
C4 | 0.061 (2) | 0.088 (2) | 0.083 (2) | 0.0019 (17) | 0.0072 (17) | −0.0069 (19) |
C5 | 0.0627 (19) | 0.070 (2) | 0.0667 (19) | 0.0064 (15) | 0.0046 (15) | 0.0015 (16) |
C6 | 0.0607 (17) | 0.0449 (15) | 0.0492 (15) | −0.0006 (12) | 0.0076 (12) | −0.0016 (11) |
C7 | 0.0587 (17) | 0.0467 (15) | 0.0565 (16) | 0.0035 (12) | 0.0039 (13) | 0.0043 (13) |
C8 | 0.0540 (16) | 0.0437 (14) | 0.0567 (16) | 0.0053 (11) | 0.0032 (12) | 0.0052 (12) |
C9 | 0.0545 (17) | 0.0505 (15) | 0.0603 (17) | −0.0017 (12) | −0.0031 (13) | −0.0034 (13) |
C10 | 0.0613 (18) | 0.0482 (15) | 0.0569 (16) | 0.0027 (12) | 0.0036 (13) | −0.0027 (13) |
C11 | 0.0544 (17) | 0.0446 (15) | 0.0727 (19) | 0.0032 (12) | 0.0010 (14) | −0.0049 (13) |
C12 | 0.0598 (19) | 0.0595 (18) | 0.083 (2) | 0.0052 (14) | −0.0134 (16) | −0.0228 (16) |
C13 | 0.067 (2) | 0.0611 (18) | 0.0575 (17) | 0.0132 (14) | −0.0039 (14) | −0.0113 (14) |
O1 | 0.0743 (14) | 0.0904 (16) | 0.0639 (13) | 0.0121 (11) | 0.0139 (10) | 0.0304 (12) |
O2 | 0.0593 (12) | 0.0684 (13) | 0.0569 (12) | 0.0094 (9) | 0.0094 (9) | 0.0141 (10) |
C14 | 0.057 (3) | 0.059 (3) | 0.077 (3) | 0.004 (3) | 0.001 (3) | −0.009 (3) |
C15 | 0.056 (3) | 0.064 (3) | 0.087 (4) | 0.001 (3) | 0.018 (3) | −0.001 (3) |
C16 | 0.065 (2) | 0.0484 (19) | 0.071 (2) | 0.0033 (16) | 0.015 (2) | −0.0013 (17) |
O4 | 0.074 (3) | 0.082 (3) | 0.065 (3) | −0.010 (3) | 0.013 (3) | 0.005 (3) |
C20 | 0.056 (2) | 0.0449 (19) | 0.0518 (19) | 0.0005 (15) | 0.0107 (16) | −0.0033 (16) |
C21 | 0.060 (2) | 0.0455 (19) | 0.053 (2) | −0.0032 (16) | 0.0162 (17) | −0.0025 (15) |
C22 | 0.063 (3) | 0.0454 (19) | 0.056 (2) | 0.0036 (18) | 0.013 (2) | 0.0043 (16) |
C17 | 0.065 (3) | 0.040 (2) | 0.051 (2) | 0.0039 (19) | 0.013 (2) | 0.0008 (17) |
C18 | 0.060 (2) | 0.048 (2) | 0.063 (3) | −0.0060 (16) | 0.0084 (18) | 0.0041 (18) |
C19 | 0.068 (3) | 0.051 (2) | 0.053 (2) | −0.001 (2) | 0.015 (2) | 0.0058 (19) |
O3 | 0.058 (3) | 0.125 (3) | 0.091 (3) | 0.003 (3) | 0.013 (2) | −0.003 (3) |
C23 | 0.062 (3) | 0.101 (5) | 0.056 (4) | −0.007 (3) | 0.005 (3) | −0.004 (3) |
C14' | 0.034 (8) | 0.062 (9) | 0.086 (12) | 0.019 (8) | −0.030 (9) | −0.010 (11) |
C15' | 0.023 (6) | 0.050 (6) | 0.044 (6) | −0.002 (5) | 0.012 (5) | 0.006 (5) |
C16' | 0.040 (7) | 0.041 (6) | 0.049 (8) | −0.002 (7) | 0.035 (6) | 0.006 (6) |
O4' | 0.054 (10) | 0.061 (10) | 0.066 (10) | −0.015 (9) | 0.018 (9) | 0.003 (10) |
C20' | 0.066 (7) | 0.056 (7) | 0.064 (7) | −0.012 (6) | −0.001 (6) | −0.012 (7) |
C21' | 0.047 (8) | 0.050 (7) | 0.055 (7) | −0.003 (6) | 0.020 (6) | −0.003 (6) |
C22' | 0.053 (8) | 0.054 (8) | 0.031 (6) | 0.007 (7) | 0.025 (7) | 0.017 (6) |
C17' | 0.056 (6) | 0.039 (6) | 0.041 (6) | −0.009 (5) | 0.035 (5) | 0.007 (5) |
C18' | 0.095 (9) | 0.063 (8) | 0.051 (8) | 0.007 (7) | 0.007 (7) | 0.000 (7) |
C19' | 0.068 (8) | 0.054 (8) | 0.067 (8) | −0.008 (8) | −0.002 (7) | −0.001 (7) |
O3' | 0.045 (9) | 0.111 (11) | 0.070 (11) | 0.009 (8) | −0.016 (7) | −0.006 (11) |
C23' | 0.15 (3) | 0.079 (19) | 0.051 (17) | 0.015 (19) | −0.010 (18) | 0.029 (18) |
C1—C2 | 1.371 (4) | C20—C21 | 1.3900 |
C1—C6 | 1.389 (4) | C20—C19 | 1.3900 |
C1—H1 | 0.9300 | C21—C22 | 1.3900 |
C2—C3 | 1.366 (5) | C21—H21 | 0.9300 |
C2—H2 | 0.9300 | C22—C17 | 1.3900 |
C3—C4 | 1.381 (5) | C22—H22 | 0.9300 |
C3—H3 | 0.9300 | C17—C18 | 1.3900 |
C4—C5 | 1.372 (4) | C18—C19 | 1.3900 |
C4—H4 | 0.9300 | C18—H18 | 0.9300 |
C5—C6 | 1.379 (4) | C19—H19 | 0.9300 |
C5—H5 | 0.9300 | C23—H23A | 0.9600 |
C6—C7 | 1.476 (4) | C23—H23B | 0.9600 |
C7—O1 | 1.196 (3) | C23—H23C | 0.9600 |
C7—O2 | 1.351 (3) | C14'—O3' | 1.234 (11) |
C8—C13 | 1.361 (4) | C14'—C15' | 1.60 (2) |
C8—C9 | 1.379 (4) | C15'—C16' | 1.38 (3) |
C8—O2 | 1.403 (3) | C15'—H15' | 0.9300 |
C9—C10 | 1.376 (4) | C16'—C17' | 1.45 (2) |
C9—H9 | 0.9300 | C16'—H16' | 0.9300 |
C10—C11 | 1.391 (4) | O4'—C23' | 1.426 (9) |
C10—H10 | 0.9300 | O4'—C20' | 1.6236 |
C11—C12 | 1.389 (4) | C20'—C21' | 1.3900 |
C11—C14 | 1.484 (5) | C20'—C19' | 1.3900 |
C11—C14' | 1.505 (10) | C21'—C22' | 1.3900 |
C12—C13 | 1.367 (4) | C21'—H21' | 0.9300 |
C12—H12 | 0.9300 | C22'—C17' | 1.3900 |
C13—H13 | 0.9300 | C22'—H22' | 0.9300 |
C14—O3 | 1.222 (6) | C17'—C18' | 1.3900 |
C14—C15 | 1.460 (7) | C18'—C19' | 1.3900 |
C15—C16 | 1.297 (6) | C18'—H18' | 0.9300 |
C15—H15 | 0.9300 | C19'—H19' | 0.9300 |
C16—C17 | 1.480 (4) | C23'—H23D | 0.9600 |
C16—H16 | 0.9300 | C23'—H23E | 0.9600 |
O4—C20 | 1.3287 | C23'—H23F | 0.9600 |
O4—C23 | 1.421 (5) | ||
C2—C1—C6 | 119.3 (3) | O4—C20—C21 | 113.5 |
C2—C1—H1 | 120.3 | O4—C20—C19 | 126.3 |
C6—C1—H1 | 120.3 | C21—C20—C19 | 120.0 |
C3—C2—C1 | 121.3 (3) | C22—C21—C20 | 120.0 |
C3—C2—H2 | 119.4 | C22—C21—H21 | 120.0 |
C1—C2—H2 | 119.4 | C20—C21—H21 | 120.0 |
C2—C3—C4 | 119.6 (3) | C21—C22—C17 | 120.0 |
C2—C3—H3 | 120.2 | C21—C22—H22 | 120.0 |
C4—C3—H3 | 120.2 | C17—C22—H22 | 120.0 |
C5—C4—C3 | 119.8 (3) | C22—C17—C18 | 120.0 |
C5—C4—H4 | 120.1 | C22—C17—C16 | 116.38 (18) |
C3—C4—H4 | 120.1 | C18—C17—C16 | 123.54 (18) |
C4—C5—C6 | 120.6 (3) | C17—C18—C19 | 120.0 |
C4—C5—H5 | 119.7 | C17—C18—H18 | 120.0 |
C6—C5—H5 | 119.7 | C19—C18—H18 | 120.0 |
C5—C6—C1 | 119.4 (3) | C18—C19—C20 | 120.0 |
C5—C6—C7 | 118.0 (3) | C18—C19—H19 | 120.0 |
C1—C6—C7 | 122.6 (3) | C20—C19—H19 | 120.0 |
O1—C7—O2 | 123.0 (3) | O3'—C14'—C11 | 131.7 (18) |
O1—C7—C6 | 125.4 (3) | O3'—C14'—C15' | 106.0 (12) |
O2—C7—C6 | 111.6 (2) | C11—C14'—C15' | 122.3 (13) |
C13—C8—C9 | 121.3 (3) | C16'—C15'—C14' | 120.6 (15) |
C13—C8—O2 | 116.7 (3) | C16'—C15'—H15' | 119.7 |
C9—C8—O2 | 121.7 (2) | C14'—C15'—H15' | 119.7 |
C10—C9—C8 | 119.1 (3) | C15'—C16'—C17' | 131.3 (16) |
C10—C9—H9 | 120.5 | C15'—C16'—H16' | 114.3 |
C8—C9—H9 | 120.5 | C17'—C16'—H16' | 114.3 |
C9—C10—C11 | 120.5 (3) | C23'—O4'—C20' | 120 (2) |
C9—C10—H10 | 119.7 | C21'—C20'—C19' | 120.0 |
C11—C10—H10 | 119.7 | C21'—C20'—O4' | 127.7 |
C12—C11—C10 | 118.6 (3) | C19'—C20'—O4' | 112.3 |
C12—C11—C14 | 119.3 (3) | C20'—C21'—C22' | 120.0 |
C10—C11—C14 | 122.1 (3) | C20'—C21'—H21' | 120.0 |
C12—C11—C14' | 134.9 (11) | C22'—C21'—H21' | 120.0 |
C10—C11—C14' | 105.2 (10) | C17'—C22'—C21' | 120.0 |
C14—C11—C14' | 20.7 (7) | C17'—C22'—H22' | 120.0 |
C13—C12—C11 | 120.8 (3) | C21'—C22'—H22' | 120.0 |
C13—C12—H12 | 119.6 | C18'—C17'—C22' | 120.0 |
C11—C12—H12 | 119.6 | C18'—C17'—C16' | 127.7 (8) |
C8—C13—C12 | 119.7 (3) | C22'—C17'—C16' | 112.1 (8) |
C8—C13—H13 | 120.1 | C17'—C18'—C19' | 120.0 |
C12—C13—H13 | 120.1 | C17'—C18'—H18' | 120.0 |
C7—O2—C8 | 120.4 (2) | C19'—C18'—H18' | 120.0 |
O3—C14—C15 | 124.1 (5) | C18'—C19'—C20' | 120.0 |
O3—C14—C11 | 117.2 (4) | C18'—C19'—H19' | 120.0 |
C15—C14—C11 | 118.7 (5) | C20'—C19'—H19' | 120.0 |
C16—C15—C14 | 120.5 (6) | O4'—C23'—H23D | 109.5 |
C16—C15—H15 | 119.7 | O4'—C23'—H23E | 109.5 |
C14—C15—H15 | 119.7 | H23D—C23'—H23E | 109.5 |
C15—C16—C17 | 125.9 (5) | O4'—C23'—H23F | 109.5 |
C15—C16—H16 | 117.0 | H23D—C23'—H23F | 109.5 |
C17—C16—H16 | 117.0 | H23E—C23'—H23F | 109.5 |
C20—O4—C23 | 117.6 (4) | ||
C6—C1—C2—C3 | 0.9 (5) | C23—O4—C20—C21 | 171.5 (7) |
C1—C2—C3—C4 | −0.2 (5) | C23—O4—C20—C19 | −3.9 (7) |
C2—C3—C4—C5 | −0.8 (5) | O4—C20—C21—C22 | −175.8 |
C3—C4—C5—C6 | 1.0 (5) | C19—C20—C21—C22 | 0.0 |
C4—C5—C6—C1 | −0.2 (5) | C20—C21—C22—C17 | 0.0 |
C4—C5—C6—C7 | −179.6 (3) | C21—C22—C17—C18 | 0.0 |
C2—C1—C6—C5 | −0.8 (4) | C21—C22—C17—C16 | 176.82 (17) |
C2—C1—C6—C7 | 178.6 (3) | C15—C16—C17—C22 | 167.8 (4) |
C5—C6—C7—O1 | −5.3 (4) | C15—C16—C17—C18 | −15.6 (5) |
C1—C6—C7—O1 | 175.3 (3) | C22—C17—C18—C19 | 0.0 |
C5—C6—C7—O2 | 174.1 (2) | C16—C17—C18—C19 | −176.58 (18) |
C1—C6—C7—O2 | −5.3 (4) | C17—C18—C19—C20 | 0.0 |
C13—C8—C9—C10 | 0.4 (4) | O4—C20—C19—C18 | 175.2 |
O2—C8—C9—C10 | 174.3 (2) | C21—C20—C19—C18 | 0.0 |
C8—C9—C10—C11 | −1.7 (4) | C12—C11—C14'—O3' | 150 (3) |
C9—C10—C11—C12 | 1.6 (4) | C10—C11—C14'—O3' | −16 (4) |
C9—C10—C11—C14 | −176.5 (4) | C14—C11—C14'—O3' | −163 (8) |
C9—C10—C11—C14' | 170.5 (15) | C12—C11—C14'—C15' | −27 (4) |
C10—C11—C12—C13 | −0.1 (5) | C10—C11—C14'—C15' | 166 (2) |
C14—C11—C12—C13 | 178.0 (4) | C14—C11—C14'—C15' | 19 (2) |
C14'—C11—C12—C13 | −164.9 (18) | O3'—C14'—C15'—C16' | 159 (2) |
C9—C8—C13—C12 | 1.0 (4) | C11—C14'—C15'—C16' | −23 (4) |
O2—C8—C13—C12 | −173.1 (3) | C14'—C15'—C16'—C17' | −177 (2) |
C11—C12—C13—C8 | −1.2 (5) | C23'—O4'—C20'—C21' | −179 (3) |
O1—C7—O2—C8 | −0.2 (4) | C23'—O4'—C20'—C19' | 0 (3) |
C6—C7—O2—C8 | −179.6 (2) | C19'—C20'—C21'—C22' | 0.0 |
C13—C8—O2—C7 | −126.4 (3) | O4'—C20'—C21'—C22' | 178.8 |
C9—C8—O2—C7 | 59.5 (3) | C20'—C21'—C22'—C17' | 0.0 |
C12—C11—C14—O3 | 155.5 (5) | C21'—C22'—C17'—C18' | 0.0 |
C10—C11—C14—O3 | −26.5 (8) | C21'—C22'—C17'—C16' | 175.2 (10) |
C14'—C11—C14—O3 | 12 (4) | C15'—C16'—C17'—C18' | 167.7 (15) |
C12—C11—C14—C15 | −25.0 (7) | C15'—C16'—C17'—C22' | −7 (2) |
C10—C11—C14—C15 | 153.0 (5) | C22'—C17'—C18'—C19' | 0.0 |
C14'—C11—C14—C15 | −169 (5) | C16'—C17'—C18'—C19' | −174.4 (11) |
O3—C14—C15—C16 | −18.4 (10) | C17'—C18'—C19'—C20' | 0.0 |
C11—C14—C15—C16 | 162.1 (5) | C21'—C20'—C19'—C18' | 0.0 |
C14—C15—C16—C17 | 178.2 (4) | O4'—C20'—C19'—C18' | −178.9 |
D—H···A | D—H | H···A | D···A | D—H···A |
C21—H21···O1i | 0.93 | 2.56 | 3.280 (3) | 135 |
C21′—H21′···O1i | 0.93 | 2.65 | 3.546 (7) | 163 |
C23′—H23F···O1ii | 0.96 | 2.50 | 3.24 (7) | 135 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C21—H21···O1i | 0.93 | 2.56 | 3.280 (3) | 135 |
C21'—H21'···O1i | 0.93 | 2.65 | 3.546 (7) | 163 |
C23'—H23F···O1ii | 0.96 | 2.50 | 3.24 (7) | 135 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+1, −z. |
Acknowledgements
The authors thank Professor D. Velmurugan, Centre for Advanced Study in Crystallography and Biophysics, University of Madras, for providing data-collection and computer facilities.
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Flavonoids belong to a large group of abundant plant secondary metabolites, which can be found in vascular plants such as ferns, conifers and flowering plants (Di Carlo et al.,1999). Natural and synthetic flavonoids are therefore of considerable interest in the development of new therapeutic agents for various diseases and are generally believed to be non-toxic compounds since they are widely distributed in the human diet (Rackova et al.., 2005; Harborne et al., 2000).
In the compound, the phenyl benzoate and chalcone groups are linked by a phenyl ring (B). The C—O bond length 1.219 (6) Å indicate the double bond character. The C—O bond length of phenyl benzoate 1.403 (4) & 1.197 (4) Å, respectively, indicate the single and double bond characters and are comparable with similar reported structure [Moreno-Fuquen et al.,2014]. The bond angles C11—C14—C15(118.7 (5)°, C15—C16—C17(125.9 (5)°) are slightly shorter than the normal values but are comparable with those in similar reported structure [Sathya et al.,2014 & Jasinski et al.,2011]. This may be due to the presence of keto group and the associated steric forces. The prop-2-en-1-one group is twisted slightly with a C15—C16—C17—C22 & C12—C11—C14—O3 torsion angle of [167.8 (4)° & 155.5 (5)°], respectively, and are in good agreement with similar reported structures (Sathya et al., 2014 & Jasinski et al., 2011). The central ester moiety[O1/C7/O2] is twisted(C9—C8—O2—C7/C13—C8—O2—C7) away from the benzene ring on both sides by 59.5 (3)&-126.4 (3)°, respectively, and are comparable with similar reported structure (Moreno-Fuquen et al.,2014)
In the crystal, the symmetry related molecules linked by C—H···O type hydrogen bonds forming dimer R22 (28), described by the graph set motif. These dimer units inturn linked by C—H···O type hydrogen bond results in a molecular chain running along [100] direction.