Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807044303/at2394sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807044303/at2394Isup2.hkl |
CCDC reference: 663769
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.003 Å
- R factor = 0.042
- wR factor = 0.114
- Data-to-parameter ratio = 25.9
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT707_ALERT_1_A D...A Calc 22.371(3), Rep 3.541(3), Dev.. 6276.67 Sigma C18 -O1 1.555 4.555 PLAT726_ALERT_1_A H...A Calc 23.26000, Rep 2.59000 Dev... 20.67 Ang. H18A -O1 1.555 4.555 PLAT728_ALERT_1_A D-H..A Calc 21.00, Rep 172.00 Dev... 151.00 Deg. C18 -H18A -O1 1.555 1.555 4.555
Alert level B ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75 Tmin and Tmax reported: 0.559 1.000 Tmin(prime) and Tmax expected: 0.847 0.931 RR(prime) = 0.615 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.61
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 42 Perc. PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.93 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for O3
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.931 Tmax scaled 0.931 Tmin scaled 0.521
3 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
2,3,4-Trimethoxybenzaldehyde (1.96 g, 0.01 mol) in ethanol (50 ml) was mixed with 1-(2,4-dichlorophenyl)ethanone (1.89 g, 0.01 mol) and the mixture was treated with 10 ml of 10% KOH. The reaction mixture was then kept for constant stirring. The solid precipitate obtained was filtered, washed with ethanol and dried. Crystal growth was carried out from a 1:1 mixture of acetone and toluene by the slow evaporation technique [m.p.: 327–329 K]. Analysis found: C 58.80, H 4.34%; C18H16Cl2O4 requires: C 58.87, H 4.39%.
All H atoms were placed in their calculated places and all H atoms were refined using a riding model with C—H = 0.93 to 0.96 Å, and with Uiso(H) = 1.18–1.50Ueq(C).
Chalcones are one of the major classes of natural products with widespread distribution in fruits, vegetables, spices, tea and soy based foodstuff have recently been subjects of great interest for their interesting pharmacological activities (Di Carlo et al., 1999). A vast number of naturally occurring chalcones are polyhydroxylated in the aryl rings. The radical quenching properties of the phenolic groups present in many chalcones have raised interest in using the compounds or chalcone rich plant extracts as drugs or food preservatives (Dhar, 1981). Chalcones can be easily obtained from the aldol condensation of aromatic aldehydes and aromatic ketones. This class of compounds presents interesting biological properties such as cytotoxicity (Pandey et al., 2005; Bhat et al., 2005), antiherpes activity, antitumour activity and may be useful for the chemotherapy of leishmaniasis among others (Lawrence et al., 2001). A review on the bioactivities of chalcones is described (Dimmock et al., 1999). Chalcones and their heterocyclic analogs as potential antifungal chemotherapeutic agents has been published (Opletalova & Sedivy, 1999). Chalcones and flavonoids as anti-tuberculosis agents are also reported (Lin et al., 2002). Several organic compounds reported to have NLO properties, chalcones derivatives are recognized material because of their excellent blue light transmittance and good crystallization ability (Goto et al., 1991; Indira et al., 2002; Sarojini et al., 2006). The crystal structures of some dichloro substituted chalcones, viz., (2E)-1-(2,4-dichlorophenyl)-3-(quinolin-8-yl)prop-2-en-1-one, Sarojini et al., (2007), (2E)-3-(biphenyl-4-yl)-1-(2,4-dichlorophenyl)prop-2-en-1-one, Fischer et al., (2007); (2E)-1-(2,4-dichlorophenyl)-3-[4-(methylsulfanyl)phenyl] prop-2-en-1-one Butcher et al., (2007); (2E)-1-(2,4-dichlorophenyl)-3-(4,5-dimethoxy-2-nitrophenyl) prop-2-en-1-one, Yathirajan, Mayekar, Narayana et al., (2007a), (2E)-1-(2,4-dichlorophenyl)-3-(6-methoxy-2-naphthyl) prop-2-en-1-one, Yathirajan, Mayekar, Narayana et al., (2007b), (2E)-1-(2,4-dichlorophenyl)-3-(4-nitrophenyl)prop-2-en-1-one, Yathirajan, Mayekar, Sarojini et al., (2007a) and (2E)-1-(2,4-dichlorophenyl)-3-(2-hydroxyphenyl)prop-2-en-1-one, Yathirajan, Mayekar, Sarojini et al., (2007b) have been reported. A structurally very similar compound, viz., 1-(2,4-dichlorophenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one, which crystallizes in the triclinic space group, has also been reported (Teh et al., 2006). In continuation of our work on chalcones, a new chalcone, (I), C16H13FO has been synthesized and its crystal structure reported.
The mean planes of the 2,4-dichlorophenyl and 2,3,4-trimethoxyphenyl groups are separated by a dihedral angle of 55.2 (2)° (Fig. 1). The torsion angle connecting the ketone oxygen atom to the 2,4-dichlorophenyl group [C6–C1– C7–O1] is 57.3 (2)°. Crystal packing is stabilized by intermolecular C—H···O hydrogen bonding between a methoxy hydrogen atom and the ketone oxygen atom in the prop-2-ene group which link the molecules into chains in an alternate inverted pattern parallel to the bc face and diagonal along the a axis of the unit cell (Fig. 2).
For related structures, see: Teh et al. (2006); Sarojini et al. (2007); Fischer et al. (2007); Butcher et al. (2007); Yathirajan, Mayekar, Narayana et al. (2007a,b); Yathirajan, Mayekar, Sarojini et al. (2007a,b). For related literature, see: Dhar, (1981); Di Carlo et al. (1999); Dimmock et al. (1999); Goto et al. (1991); Opletalova & Sedivy, (1999); Indira et al. (2002); Lawrence et al. (2001); Bhat et al. (2005); Pandey et al. (2005); Sarojini et al. (2006); Lin et al. (2002).
Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis PRO (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).
C18H16Cl2O4 | F(000) = 760 |
Mr = 367.21 | Dx = 1.414 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3324 reflections |
a = 16.5354 (7) Å | θ = 4.6–32.5° |
b = 4.6157 (2) Å | µ = 0.40 mm−1 |
c = 23.1486 (11) Å | T = 296 K |
β = 102.489 (5)° | Chunk, colourless |
V = 1724.95 (13) Å3 | 0.41 × 0.37 × 0.18 mm |
Z = 4 |
Oxford Diffraction Gemini R CCD diffractometer | 5691 independent reflections |
Radiation source: fine-focus sealed tube | 2371 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
Detector resolution: 10.5081 pixels mm-1 | θmax = 32.5°, θmin = 4.6° |
φ and ω scans | h = −24→22 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | k = −6→6 |
Tmin = 0.559, Tmax = 1.000 | l = −34→32 |
14451 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.114 | H-atom parameters constrained |
S = 0.88 | w = 1/[σ2(Fo2) + (0.0519P)2] where P = (Fo2 + 2Fc2)/3 |
5691 reflections | (Δ/σ)max = 0.009 |
220 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.42 e Å−3 |
C18H16Cl2O4 | V = 1724.95 (13) Å3 |
Mr = 367.21 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 16.5354 (7) Å | µ = 0.40 mm−1 |
b = 4.6157 (2) Å | T = 296 K |
c = 23.1486 (11) Å | 0.41 × 0.37 × 0.18 mm |
β = 102.489 (5)° |
Oxford Diffraction Gemini R CCD diffractometer | 5691 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | 2371 reflections with I > 2σ(I) |
Tmin = 0.559, Tmax = 1.000 | Rint = 0.042 |
14451 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.114 | H-atom parameters constrained |
S = 0.88 | Δρmax = 0.24 e Å−3 |
5691 reflections | Δρmin = −0.42 e Å−3 |
220 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 | ||
Cl1 | 0.65714 (3) | 0.57002 (10) | 0.00083 (2) | 0.04970 (15) | |
Cl2 | 0.41613 (3) | −0.11621 (12) | −0.11266 (3) | 0.06282 (18) | |
O1 | 0.77809 (8) | 0.4482 (3) | −0.12937 (6) | 0.0636 (4) | |
O2 | 0.79104 (7) | −0.0644 (2) | 0.11903 (6) | 0.0446 (3) | |
O3 | 0.91524 (8) | −0.1181 (3) | 0.22328 (5) | 0.0451 (3) | |
O4 | 1.07048 (8) | 0.0060 (4) | 0.22270 (6) | 0.0633 (4) | |
C1 | 0.67810 (10) | 0.2144 (4) | −0.08863 (7) | 0.0352 (4) | |
C2 | 0.62533 (11) | 0.3090 (4) | −0.05314 (7) | 0.0356 (4) | |
C3 | 0.54519 (10) | 0.2092 (4) | −0.06074 (8) | 0.0383 (4) | |
H3A | 0.5108 | 0.2750 | −0.0366 | 0.046* | |
C4 | 0.51694 (11) | 0.0103 (4) | −0.10476 (8) | 0.0400 (4) | |
C5 | 0.56629 (12) | −0.0876 (4) | −0.14163 (8) | 0.0444 (5) | |
H5A | 0.5463 | −0.2205 | −0.1715 | 0.053* | |
C6 | 0.64602 (11) | 0.0170 (4) | −0.13296 (8) | 0.0433 (4) | |
H6A | 0.6797 | −0.0470 | −0.1577 | 0.052* | |
C7 | 0.76435 (11) | 0.3273 (4) | −0.08525 (8) | 0.0422 (4) | |
C8 | 0.83050 (11) | 0.2903 (5) | −0.03338 (8) | 0.0499 (5) | |
H8A | 0.8807 | 0.3808 | −0.0336 | 0.060* | |
C9 | 0.82552 (11) | 0.1376 (4) | 0.01465 (8) | 0.0404 (4) | |
H9A | 0.7751 | 0.0483 | 0.0147 | 0.048* | |
C10 | 0.89131 (10) | 0.0970 (4) | 0.06698 (7) | 0.0410 (4) | |
C11 | 0.87263 (10) | −0.0097 (4) | 0.11940 (8) | 0.0361 (4) | |
C12 | 0.93420 (11) | −0.0322 (4) | 0.17086 (7) | 0.0400 (4) | |
C13 | 1.01539 (12) | 0.0394 (4) | 0.17032 (8) | 0.0492 (5) | |
C14 | 1.03516 (12) | 0.1401 (5) | 0.11867 (9) | 0.0636 (6) | |
H14A | 1.0896 | 0.1874 | 0.1179 | 0.076* | |
C15 | 0.97344 (12) | 0.1694 (5) | 0.06859 (8) | 0.0600 (6) | |
H15A | 0.9872 | 0.2405 | 0.0344 | 0.072* | |
C16 | 0.77199 (13) | −0.3329 (4) | 0.14340 (10) | 0.0583 (6) | |
H16A | 0.7146 | −0.3783 | 0.1285 | 0.087* | |
H16B | 0.7827 | −0.3178 | 0.1857 | 0.087* | |
H16C | 0.8058 | −0.4834 | 0.1324 | 0.087* | |
C17 | 0.8940 (2) | 0.1146 (5) | 0.25695 (10) | 0.0837 (8) | |
H17A | 0.8905 | 0.0460 | 0.2955 | 0.126* | |
H17B | 0.8415 | 0.1932 | 0.2374 | 0.126* | |
H17C | 0.9357 | 0.2625 | 0.2609 | 0.126* | |
C18 | 1.15339 (13) | 0.0913 (6) | 0.22577 (10) | 0.0749 (8) | |
H18A | 1.1852 | 0.0614 | 0.2652 | 0.112* | |
H18B | 1.1549 | 0.2926 | 0.2157 | 0.112* | |
H18C | 1.1764 | −0.0223 | 0.1985 | 0.112* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0552 (3) | 0.0458 (3) | 0.0467 (3) | −0.0095 (2) | 0.0080 (2) | −0.0104 (2) |
Cl2 | 0.0410 (3) | 0.0749 (4) | 0.0710 (4) | −0.0196 (3) | 0.0088 (3) | −0.0084 (3) |
O1 | 0.0458 (8) | 0.1031 (11) | 0.0399 (8) | −0.0141 (8) | 0.0048 (6) | 0.0244 (8) |
O2 | 0.0319 (7) | 0.0504 (7) | 0.0514 (8) | −0.0007 (6) | 0.0089 (6) | 0.0181 (6) |
O3 | 0.0468 (8) | 0.0556 (8) | 0.0335 (7) | 0.0021 (6) | 0.0100 (6) | 0.0109 (6) |
O4 | 0.0391 (8) | 0.1088 (11) | 0.0364 (7) | −0.0063 (8) | −0.0041 (6) | 0.0165 (8) |
C1 | 0.0334 (9) | 0.0417 (9) | 0.0280 (9) | −0.0002 (8) | 0.0012 (7) | 0.0093 (8) |
C2 | 0.0402 (10) | 0.0358 (9) | 0.0282 (9) | −0.0019 (8) | 0.0014 (7) | 0.0012 (7) |
C3 | 0.0354 (10) | 0.0409 (10) | 0.0391 (10) | −0.0004 (8) | 0.0093 (8) | 0.0029 (8) |
C4 | 0.0339 (10) | 0.0436 (10) | 0.0400 (10) | −0.0046 (8) | 0.0020 (8) | 0.0038 (8) |
C5 | 0.0443 (11) | 0.0484 (11) | 0.0377 (10) | −0.0038 (9) | 0.0024 (8) | −0.0057 (9) |
C6 | 0.0408 (11) | 0.0545 (11) | 0.0353 (10) | −0.0001 (9) | 0.0094 (8) | −0.0014 (9) |
C7 | 0.0355 (10) | 0.0575 (11) | 0.0329 (10) | −0.0068 (9) | 0.0063 (8) | 0.0085 (9) |
C8 | 0.0315 (10) | 0.0737 (13) | 0.0418 (11) | −0.0133 (9) | 0.0019 (8) | 0.0148 (10) |
C9 | 0.0296 (9) | 0.0520 (10) | 0.0379 (10) | −0.0068 (8) | 0.0035 (8) | 0.0036 (9) |
C10 | 0.0308 (9) | 0.0588 (12) | 0.0313 (9) | −0.0033 (8) | 0.0023 (7) | 0.0071 (9) |
C11 | 0.0301 (9) | 0.0411 (9) | 0.0366 (9) | 0.0006 (7) | 0.0063 (7) | 0.0063 (8) |
C12 | 0.0378 (10) | 0.0499 (10) | 0.0316 (9) | 0.0018 (8) | 0.0058 (8) | 0.0091 (8) |
C13 | 0.0356 (10) | 0.0770 (13) | 0.0321 (10) | −0.0017 (10) | 0.0010 (8) | 0.0096 (10) |
C14 | 0.0319 (10) | 0.1145 (18) | 0.0419 (11) | −0.0139 (11) | 0.0028 (9) | 0.0177 (12) |
C15 | 0.0399 (11) | 0.1047 (17) | 0.0341 (11) | −0.0113 (11) | 0.0050 (9) | 0.0210 (11) |
C16 | 0.0546 (13) | 0.0536 (12) | 0.0642 (14) | −0.0170 (10) | 0.0074 (11) | 0.0151 (11) |
C17 | 0.130 (2) | 0.0801 (17) | 0.0473 (14) | 0.0262 (16) | 0.0334 (15) | 0.0085 (12) |
C18 | 0.0372 (12) | 0.135 (2) | 0.0454 (13) | −0.0092 (13) | −0.0078 (9) | 0.0080 (13) |
Cl1—C2 | 1.7335 (17) | C8—H8A | 0.9300 |
Cl2—C4 | 1.7382 (18) | C9—C10 | 1.455 (2) |
O1—C7 | 1.227 (2) | C9—H9A | 0.9300 |
O2—C11 | 1.3707 (19) | C10—C15 | 1.391 (2) |
O2—C16 | 1.425 (2) | C10—C11 | 1.405 (2) |
O3—C12 | 1.3757 (19) | C11—C12 | 1.393 (2) |
O3—C17 | 1.415 (2) | C12—C13 | 1.385 (2) |
O4—C13 | 1.359 (2) | C13—C14 | 1.386 (3) |
O4—C18 | 1.413 (2) | C14—C15 | 1.375 (2) |
C1—C6 | 1.389 (2) | C14—H14A | 0.9300 |
C1—C2 | 1.392 (2) | C15—H15A | 0.9300 |
C1—C7 | 1.504 (2) | C16—H16A | 0.9600 |
C2—C3 | 1.378 (2) | C16—H16B | 0.9600 |
C3—C4 | 1.376 (2) | C16—H16C | 0.9600 |
C3—H3A | 0.9300 | C17—H17A | 0.9600 |
C4—C5 | 1.378 (3) | C17—H17B | 0.9600 |
C5—C6 | 1.377 (3) | C17—H17C | 0.9600 |
C5—H5A | 0.9300 | C18—H18A | 0.9600 |
C6—H6A | 0.9300 | C18—H18B | 0.9600 |
C7—C8 | 1.449 (2) | C18—H18C | 0.9600 |
C8—C9 | 1.334 (2) | ||
C11—O2—C16 | 117.36 (14) | O2—C11—C12 | 121.86 (15) |
C12—O3—C17 | 113.45 (15) | O2—C11—C10 | 117.34 (15) |
C13—O4—C18 | 117.98 (15) | C12—C11—C10 | 120.54 (16) |
C6—C1—C2 | 116.99 (16) | O3—C12—C13 | 118.87 (15) |
C6—C1—C7 | 118.17 (16) | O3—C12—C11 | 120.78 (16) |
C2—C1—C7 | 124.67 (16) | C13—C12—C11 | 120.32 (16) |
C3—C2—C1 | 121.87 (16) | O4—C13—C12 | 115.40 (16) |
C3—C2—Cl1 | 117.27 (14) | O4—C13—C14 | 124.76 (18) |
C1—C2—Cl1 | 120.81 (13) | C12—C13—C14 | 119.84 (17) |
C4—C3—C2 | 118.74 (16) | C15—C14—C13 | 119.31 (18) |
C4—C3—H3A | 120.6 | C15—C14—H14A | 120.3 |
C2—C3—H3A | 120.6 | C13—C14—H14A | 120.3 |
C3—C4—C5 | 121.71 (16) | C14—C15—C10 | 122.76 (17) |
C3—C4—Cl2 | 117.80 (14) | C14—C15—H15A | 118.6 |
C5—C4—Cl2 | 120.49 (14) | C10—C15—H15A | 118.6 |
C6—C5—C4 | 118.09 (17) | O2—C16—H16A | 109.5 |
C6—C5—H5A | 121.0 | O2—C16—H16B | 109.5 |
C4—C5—H5A | 121.0 | H16A—C16—H16B | 109.5 |
C5—C6—C1 | 122.57 (17) | O2—C16—H16C | 109.5 |
C5—C6—H6A | 118.7 | H16A—C16—H16C | 109.5 |
C1—C6—H6A | 118.7 | H16B—C16—H16C | 109.5 |
O1—C7—C8 | 120.05 (16) | O3—C17—H17A | 109.5 |
O1—C7—C1 | 117.26 (15) | O3—C17—H17B | 109.5 |
C8—C7—C1 | 122.67 (15) | H17A—C17—H17B | 109.5 |
C9—C8—C7 | 125.54 (17) | O3—C17—H17C | 109.5 |
C9—C8—H8A | 117.2 | H17A—C17—H17C | 109.5 |
C7—C8—H8A | 117.2 | H17B—C17—H17C | 109.5 |
C8—C9—C10 | 126.31 (16) | O4—C18—H18A | 109.5 |
C8—C9—H9A | 116.8 | O4—C18—H18B | 109.5 |
C10—C9—H9A | 116.8 | H18A—C18—H18B | 109.5 |
C15—C10—C11 | 117.18 (16) | O4—C18—H18C | 109.5 |
C15—C10—C9 | 122.78 (16) | H18A—C18—H18C | 109.5 |
C11—C10—C9 | 120.00 (15) | H18B—C18—H18C | 109.5 |
C6—C1—C2—C3 | 0.9 (2) | C16—O2—C11—C10 | 133.69 (18) |
C7—C1—C2—C3 | 176.10 (15) | C15—C10—C11—O2 | 176.11 (17) |
C6—C1—C2—Cl1 | −176.44 (13) | C9—C10—C11—O2 | −1.7 (2) |
C7—C1—C2—Cl1 | −1.3 (2) | C15—C10—C11—C12 | 1.9 (3) |
C1—C2—C3—C4 | 0.0 (3) | C9—C10—C11—C12 | −175.92 (16) |
Cl1—C2—C3—C4 | 177.48 (13) | C17—O3—C12—C13 | 89.1 (2) |
C2—C3—C4—C5 | −0.9 (3) | C17—O3—C12—C11 | −89.2 (2) |
C2—C3—C4—Cl2 | 179.03 (13) | O2—C11—C12—O3 | 1.7 (3) |
C3—C4—C5—C6 | 0.7 (3) | C10—C11—C12—O3 | 175.61 (16) |
Cl2—C4—C5—C6 | −179.19 (14) | O2—C11—C12—C13 | −176.60 (17) |
C4—C5—C6—C1 | 0.3 (3) | C10—C11—C12—C13 | −2.7 (3) |
C2—C1—C6—C5 | −1.1 (3) | C18—O4—C13—C12 | −176.4 (2) |
C7—C1—C6—C5 | −176.61 (16) | C18—O4—C13—C14 | 2.9 (3) |
C6—C1—C7—O1 | 57.3 (2) | O3—C12—C13—O4 | 2.5 (3) |
C2—C1—C7—O1 | −117.8 (2) | C11—C12—C13—O4 | −179.19 (16) |
C6—C1—C7—C8 | −120.8 (2) | O3—C12—C13—C14 | −176.84 (18) |
C2—C1—C7—C8 | 64.1 (3) | C11—C12—C13—C14 | 1.5 (3) |
O1—C7—C8—C9 | −172.7 (2) | O4—C13—C14—C15 | −178.9 (2) |
C1—C7—C8—C9 | 5.3 (3) | C12—C13—C14—C15 | 0.4 (3) |
C7—C8—C9—C10 | 179.72 (18) | C13—C14—C15—C10 | −1.2 (4) |
C8—C9—C10—C15 | −12.7 (3) | C11—C10—C15—C14 | 0.0 (3) |
C8—C9—C10—C11 | 165.01 (19) | C9—C10—C15—C14 | 177.8 (2) |
C16—O2—C11—C12 | −52.2 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9A···O2 | 0.93 | 2.43 | 2.762 (2) | 101 |
C16—H16B···O3 | 0.96 | 2.36 | 2.849 (3) | 111 |
C18—H18A···O1i | 0.96 | 2.59 | 3.541 (3) | 172 |
Symmetry code: (i) x−1/2, −y−1/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C18H16Cl2O4 |
Mr | 367.21 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 296 |
a, b, c (Å) | 16.5354 (7), 4.6157 (2), 23.1486 (11) |
β (°) | 102.489 (5) |
V (Å3) | 1724.95 (13) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.40 |
Crystal size (mm) | 0.41 × 0.37 × 0.18 |
Data collection | |
Diffractometer | Oxford Diffraction Gemini R CCD |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2007) |
Tmin, Tmax | 0.559, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14451, 5691, 2371 |
Rint | 0.042 |
(sin θ/λ)max (Å−1) | 0.756 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.114, 0.88 |
No. of reflections | 5691 |
No. of parameters | 220 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.24, −0.42 |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000).
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9A···O2 | 0.93 | 2.43 | 2.762 (2) | 101 |
C16—H16B···O3 | 0.96 | 2.36 | 2.849 (3) | 111 |
C18—H18A···O1i | 0.96 | 2.59 | 3.541 (3) | 172 |
Symmetry code: (i) x−1/2, −y−1/2, z−1/2. |
Chalcones are one of the major classes of natural products with widespread distribution in fruits, vegetables, spices, tea and soy based foodstuff have recently been subjects of great interest for their interesting pharmacological activities (Di Carlo et al., 1999). A vast number of naturally occurring chalcones are polyhydroxylated in the aryl rings. The radical quenching properties of the phenolic groups present in many chalcones have raised interest in using the compounds or chalcone rich plant extracts as drugs or food preservatives (Dhar, 1981). Chalcones can be easily obtained from the aldol condensation of aromatic aldehydes and aromatic ketones. This class of compounds presents interesting biological properties such as cytotoxicity (Pandey et al., 2005; Bhat et al., 2005), antiherpes activity, antitumour activity and may be useful for the chemotherapy of leishmaniasis among others (Lawrence et al., 2001). A review on the bioactivities of chalcones is described (Dimmock et al., 1999). Chalcones and their heterocyclic analogs as potential antifungal chemotherapeutic agents has been published (Opletalova & Sedivy, 1999). Chalcones and flavonoids as anti-tuberculosis agents are also reported (Lin et al., 2002). Several organic compounds reported to have NLO properties, chalcones derivatives are recognized material because of their excellent blue light transmittance and good crystallization ability (Goto et al., 1991; Indira et al., 2002; Sarojini et al., 2006). The crystal structures of some dichloro substituted chalcones, viz., (2E)-1-(2,4-dichlorophenyl)-3-(quinolin-8-yl)prop-2-en-1-one, Sarojini et al., (2007), (2E)-3-(biphenyl-4-yl)-1-(2,4-dichlorophenyl)prop-2-en-1-one, Fischer et al., (2007); (2E)-1-(2,4-dichlorophenyl)-3-[4-(methylsulfanyl)phenyl] prop-2-en-1-one Butcher et al., (2007); (2E)-1-(2,4-dichlorophenyl)-3-(4,5-dimethoxy-2-nitrophenyl) prop-2-en-1-one, Yathirajan, Mayekar, Narayana et al., (2007a), (2E)-1-(2,4-dichlorophenyl)-3-(6-methoxy-2-naphthyl) prop-2-en-1-one, Yathirajan, Mayekar, Narayana et al., (2007b), (2E)-1-(2,4-dichlorophenyl)-3-(4-nitrophenyl)prop-2-en-1-one, Yathirajan, Mayekar, Sarojini et al., (2007a) and (2E)-1-(2,4-dichlorophenyl)-3-(2-hydroxyphenyl)prop-2-en-1-one, Yathirajan, Mayekar, Sarojini et al., (2007b) have been reported. A structurally very similar compound, viz., 1-(2,4-dichlorophenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one, which crystallizes in the triclinic space group, has also been reported (Teh et al., 2006). In continuation of our work on chalcones, a new chalcone, (I), C16H13FO has been synthesized and its crystal structure reported.
The mean planes of the 2,4-dichlorophenyl and 2,3,4-trimethoxyphenyl groups are separated by a dihedral angle of 55.2 (2)° (Fig. 1). The torsion angle connecting the ketone oxygen atom to the 2,4-dichlorophenyl group [C6–C1– C7–O1] is 57.3 (2)°. Crystal packing is stabilized by intermolecular C—H···O hydrogen bonding between a methoxy hydrogen atom and the ketone oxygen atom in the prop-2-ene group which link the molecules into chains in an alternate inverted pattern parallel to the bc face and diagonal along the a axis of the unit cell (Fig. 2).