Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807047654/at2412sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807047654/at2412Isup2.hkl |
CCDC reference: 667289
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.011 Å
- R factor = 0.081
- wR factor = 0.239
- Data-to-parameter ratio = 18.7
checkCIF/PLATON results
No syntax errors found
Alert level B ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75 Tmin and Tmax reported: 0.502 1.000 Tmin(prime) and Tmax expected: 0.777 0.858 RR(prime) = 0.554 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.55 PLAT340_ALERT_3_B Low Bond Precision on C-C Bonds (x 1000) Ang ... 11
Alert level C PLAT034_ALERT_1_C No Flack Parameter Given. Z .GT. Si, NonCentro . ? PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.86
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 0.858 Tmax scaled 0.858 Tmin scaled 0.431 REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 32.51 From the CIF: _reflns_number_total 4142 Count of symmetry unique reflns 3271 Completeness (_total/calc) 126.63% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 871 Fraction of Friedel pairs measured 0.266 Are heavy atom types Z>Si present yes PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 2
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related structures, see: Sarojini et al. (2007); Yathirajan, Mayekar, Narayana et al. (2007a,b,c; Yathirajan, Mayekar, Sarojini et al. 2007a,b). For related literature, see: Goto et al. (1991); Indira et al. (2002); Lawrence et al. (2001); Pandey et al. (2005); Sarojini et al. (2006).
3,5-Dichloro-4-methoxy-2,6-dimethylbenzaldehyde (2.33 g, 0.01 mol) in ethanol (30 ml) was mixed with 1-(2,4-dichlorophenyl)ethanone (1.89 g, 0.01 mol) in ethanol (20 ml) and the mixture was treated with 8 ml of 10% KOH solution (Fig. 4). The reaction mixture was then kept for constant stirring. The solid precipitate obtained was filtered, washed with ethanol and dried. The crystal growth was carried out from a 1:1 mixture of acetone and toluene by the slow evaporation technique (m.p.: 401–403 K). Analysis found: C 53.41, H 3.43%; C18H14Cl4O2 requires: C 53.50, H 3.49%.
All H atoms were placed in their calculated places and refined using a riding model with C—H = 0.93 to 0.96 Å, and with Uiso(H) = 1.19–1.50Ueq(C).
Chalcone is an unique template molecule that is associated with several biological activities. 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), antiherpes activity and antitumour activity and may be useful for the chemotherapy of leishmaniasis among others (Lawrence et al. 2001). Among several organic compounds reported to have NLO properties, chalcone derivatives are a 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). Structures of a few dichloro substituted chalcones viz., (2E)-1-(2,4-dichlorophenyl)-3-(quinolin-8-yl)prop-2-en-1-one (Sarojini et al. 2007), (2E)-1-(2,4-dichlorophenyl)-3-(4,5-dimethoxy-2-nitrophenyl) prop-2-en-1-one (Yathirajan, Mayekar, Narayana et al. 2007c), (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-(2-hydroxy-3-methoxyphenyl) prop-2-en-1-one (Yathirajan, Mayekar, Narayana et al. 2007a), (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 published. In continuation of our work on chalcones, a new chalcone C18H14Cl4O2 was synthesized and its crystal structure is reported.
The angle between the mean planes of the 3,5-dichloro-4-methoxy-2,6-dimethylphenyl and 2,4-dichlorophenyl groups is 47.6 (2)° (Fig. 1). The 4-methoxy group, with a C15–O2–C14–C13 torsion angle of 91.9 (9)°, is twisted away from the plane of the 3,5-dichloro-2,6-dimethylphenyl ring in an anti-clinal conformation. The ketone oxygen of the prop-2-en-1-one group is twisted in a syn-clinal conformation with the 2,4-dichlorophenyl group [C6–C1–C7–O1 torsion angle = 45.5 (11)°]. Crystal packing is stabilized by intermolecular C—H···O hydrogen bonding between the ketone oxygen from the prop-2-en-1-one group and a hydrogen atom from a nearby 2,4-dichlorophenyl group [C3–H3A···O1] which link the molecules into chains along the a axis of the unit cell (Fig. 2). Both of the 3,5-dichloro-4-methoxy-2,6-dimethylphenyl and 2,4-dichlorophenyl groups are aligned obliquely parallel to the ac face with the phenyl rings stacked obliquely along the b axis for both groups (Fig. 3).
For related structures, see: Sarojini et al. (2007); Yathirajan, Mayekar, Narayana et al. (2007a,b,c; Yathirajan, Mayekar, Sarojini et al. 2007a,b). For related literature, see: Goto et al. (1991); Indira et al. (2002); Lawrence et al. (2001); Pandey et al. (2005); Sarojini et al. (2006).
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).
C18H14Cl4O2 | F(000) = 412 |
Mr = 404.09 | Dx = 1.492 Mg m−3 |
Monoclinic, Pc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P -2yc | Cell parameters from 3151 reflections |
a = 7.8036 (4) Å | θ = 4.7–32.4° |
b = 4.3526 (2) Å | µ = 0.67 mm−1 |
c = 26.6839 (11) Å | T = 296 K |
β = 97.020 (4)° | Chunk, colourless |
V = 899.55 (7) Å3 | 0.37 × 0.31 × 0.23 mm |
Z = 2 |
Oxford Diffraction Gemini R CCD diffractometer | 4142 independent reflections |
Radiation source: fine-focus sealed tube | 2501 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.045 |
Detector resolution: 10.5081 pixels mm-1 | θmax = 32.5°, θmin = 4.8° |
φ and ω scans | h = −10→11 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | k = −6→6 |
Tmin = 0.502, Tmax = 1.000 | l = −39→39 |
8039 measured reflections |
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)] = 0.081 | H-atom parameters constrained |
wR(F2) = 0.239 | w = 1/[σ2(Fo2) + (0.128P)2 + 0.8404P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
4142 reflections | Δρmax = 0.80 e Å−3 |
221 parameters | Δρmin = −0.55 e Å−3 |
2 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.090 (11) |
C18H14Cl4O2 | V = 899.55 (7) Å3 |
Mr = 404.09 | Z = 2 |
Monoclinic, Pc | Mo Kα radiation |
a = 7.8036 (4) Å | µ = 0.67 mm−1 |
b = 4.3526 (2) Å | T = 296 K |
c = 26.6839 (11) Å | 0.37 × 0.31 × 0.23 mm |
β = 97.020 (4)° |
Oxford Diffraction Gemini R CCD diffractometer | 4142 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | 2501 reflections with I > 2σ(I) |
Tmin = 0.502, Tmax = 1.000 | Rint = 0.045 |
8039 measured reflections |
R[F2 > 2σ(F2)] = 0.081 | 2 restraints |
wR(F2) = 0.239 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.80 e Å−3 |
4142 reflections | Δρmin = −0.55 e Å−3 |
221 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 | −0.1343 (3) | −0.2032 (6) | 0.41662 (8) | 0.0672 (6) | |
Cl2 | −0.2962 (4) | 0.4321 (8) | 0.57611 (11) | 0.0929 (9) | |
Cl3 | 0.63088 (19) | 0.5365 (4) | 0.21399 (6) | 0.0454 (4) | |
Cl4 | 0.0016 (2) | −0.0404 (5) | 0.17461 (7) | 0.0546 (5) | |
O1 | 0.3767 (9) | −0.067 (2) | 0.4676 (2) | 0.083 (2) | |
O2 | 0.3069 (7) | 0.3112 (13) | 0.15441 (19) | 0.0585 (13) | |
C1 | 0.1023 (9) | 0.1380 (17) | 0.4771 (2) | 0.0471 (15) | |
C2 | −0.0731 (9) | 0.0404 (17) | 0.4674 (3) | 0.0488 (16) | |
C3 | −0.1907 (10) | 0.120 (2) | 0.4978 (3) | 0.0542 (17) | |
H3A | −0.3032 | 0.0465 | 0.4920 | 0.065* | |
C4 | −0.1405 (10) | 0.317 (2) | 0.5384 (3) | 0.0590 (19) | |
C5 | 0.0273 (13) | 0.405 (2) | 0.5501 (3) | 0.067 (2) | |
H5A | 0.0606 | 0.5270 | 0.5782 | 0.080* | |
C6 | 0.1454 (11) | 0.309 (2) | 0.5198 (3) | 0.061 (2) | |
H6A | 0.2606 | 0.3620 | 0.5285 | 0.073* | |
C7 | 0.2420 (9) | 0.0391 (17) | 0.4465 (2) | 0.0479 (15) | |
C8 | 0.2188 (10) | 0.099 (2) | 0.3920 (3) | 0.0564 (18) | |
H8A | 0.1153 | 0.1870 | 0.3780 | 0.068* | |
C9 | 0.3307 (11) | 0.038 (2) | 0.3625 (3) | 0.0554 (18) | |
H9A | 0.4312 | −0.0550 | 0.3777 | 0.067* | |
C10 | 0.3237 (9) | 0.0957 (17) | 0.3066 (3) | 0.0478 (15) | |
C11 | 0.4588 (10) | 0.2643 (17) | 0.2898 (3) | 0.0515 (16) | |
C12 | 0.6065 (11) | 0.383 (2) | 0.3266 (3) | 0.062 (2) | |
H12A | 0.7138 | 0.3094 | 0.3170 | 0.092* | |
H12B | 0.5936 | 0.3108 | 0.3599 | 0.092* | |
H12C | 0.6060 | 0.6033 | 0.3263 | 0.092* | |
C13 | 0.4546 (10) | 0.3347 (19) | 0.2390 (3) | 0.0525 (16) | |
C14 | 0.3116 (10) | 0.2325 (17) | 0.2042 (2) | 0.0485 (15) | |
C15 | 0.3859 (13) | 0.088 (2) | 0.1242 (3) | 0.062 (2) | |
H15A | 0.3837 | 0.1642 | 0.0904 | 0.093* | |
H15B | 0.3230 | −0.1015 | 0.1238 | 0.093* | |
H15C | 0.5032 | 0.0542 | 0.1386 | 0.093* | |
C16 | 0.1818 (9) | 0.0693 (16) | 0.2219 (3) | 0.0462 (15) | |
C17 | 0.1824 (10) | −0.0016 (18) | 0.2732 (3) | 0.0501 (16) | |
C18 | 0.0396 (12) | −0.197 (2) | 0.2895 (3) | 0.062 (2) | |
H18A | 0.0630 | −0.2386 | 0.3250 | 0.093* | |
H18B | 0.0332 | −0.3872 | 0.2711 | 0.093* | |
H18C | −0.0682 | −0.0899 | 0.2827 | 0.093* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0663 (12) | 0.0760 (14) | 0.0580 (10) | −0.0069 (10) | 0.0026 (8) | −0.0058 (10) |
Cl2 | 0.0866 (17) | 0.123 (2) | 0.0776 (14) | 0.0037 (16) | 0.0454 (13) | −0.0149 (15) |
Cl3 | 0.0402 (8) | 0.0484 (8) | 0.0485 (8) | −0.0094 (7) | 0.0093 (6) | 0.0048 (8) |
Cl4 | 0.0430 (9) | 0.0764 (13) | 0.0439 (8) | −0.0096 (9) | 0.0032 (7) | −0.0044 (9) |
O1 | 0.060 (4) | 0.135 (6) | 0.055 (3) | 0.013 (4) | 0.012 (3) | 0.013 (4) |
O2 | 0.076 (4) | 0.053 (3) | 0.048 (2) | 0.001 (3) | 0.013 (2) | 0.012 (2) |
C1 | 0.047 (4) | 0.057 (4) | 0.038 (3) | 0.002 (3) | 0.010 (3) | 0.005 (3) |
C2 | 0.037 (3) | 0.063 (4) | 0.047 (3) | 0.016 (3) | 0.003 (3) | 0.006 (3) |
C3 | 0.051 (4) | 0.066 (4) | 0.047 (3) | −0.004 (3) | 0.012 (3) | 0.017 (3) |
C4 | 0.054 (4) | 0.076 (5) | 0.051 (4) | 0.006 (4) | 0.020 (3) | 0.008 (4) |
C5 | 0.073 (6) | 0.084 (6) | 0.045 (4) | −0.004 (5) | 0.008 (4) | −0.011 (4) |
C6 | 0.054 (5) | 0.080 (6) | 0.047 (3) | −0.007 (4) | 0.004 (3) | 0.002 (4) |
C7 | 0.046 (4) | 0.059 (4) | 0.038 (3) | 0.007 (3) | 0.003 (3) | 0.007 (3) |
C8 | 0.048 (4) | 0.083 (5) | 0.038 (3) | 0.004 (4) | 0.006 (3) | 0.003 (3) |
C9 | 0.051 (4) | 0.071 (5) | 0.043 (3) | −0.002 (3) | 0.001 (3) | −0.006 (3) |
C10 | 0.041 (3) | 0.057 (4) | 0.047 (3) | 0.007 (3) | 0.016 (3) | 0.000 (3) |
C11 | 0.066 (4) | 0.044 (4) | 0.046 (3) | 0.002 (3) | 0.009 (3) | −0.011 (3) |
C12 | 0.046 (4) | 0.079 (6) | 0.058 (4) | 0.001 (4) | 0.000 (3) | −0.011 (4) |
C13 | 0.052 (4) | 0.058 (4) | 0.049 (3) | −0.003 (3) | 0.014 (3) | −0.002 (3) |
C14 | 0.060 (4) | 0.048 (4) | 0.038 (3) | 0.011 (3) | 0.006 (3) | 0.007 (3) |
C15 | 0.082 (6) | 0.062 (5) | 0.045 (4) | −0.002 (4) | 0.015 (4) | 0.000 (3) |
C16 | 0.042 (3) | 0.052 (4) | 0.045 (3) | 0.005 (3) | 0.005 (3) | −0.003 (3) |
C17 | 0.046 (4) | 0.062 (5) | 0.045 (3) | 0.003 (3) | 0.017 (3) | −0.003 (3) |
C18 | 0.065 (5) | 0.066 (5) | 0.059 (4) | −0.005 (4) | 0.025 (4) | −0.005 (4) |
Cl1—C2 | 1.741 (8) | C9—C10 | 1.509 (10) |
Cl2—C4 | 1.743 (8) | C9—H9A | 0.9300 |
Cl3—C13 | 1.825 (8) | C10—C17 | 1.396 (11) |
Cl4—C16 | 1.834 (7) | C10—C11 | 1.402 (11) |
O1—C7 | 1.221 (9) | C11—C13 | 1.386 (10) |
O2—C14 | 1.369 (7) | C11—C12 | 1.511 (11) |
O2—C15 | 1.445 (10) | C12—H12A | 0.9600 |
C1—C6 | 1.367 (11) | C12—H12B | 0.9600 |
C1—C2 | 1.426 (11) | C12—H12C | 0.9600 |
C1—C7 | 1.503 (10) | C13—C14 | 1.432 (11) |
C2—C3 | 1.342 (10) | C14—C16 | 1.367 (11) |
C3—C4 | 1.400 (12) | C15—H15A | 0.9600 |
C3—H3A | 0.9300 | C15—H15B | 0.9600 |
C4—C5 | 1.363 (13) | C15—H15C | 0.9600 |
C5—C6 | 1.364 (12) | C16—C17 | 1.402 (10) |
C5—H5A | 0.9300 | C17—C18 | 1.508 (11) |
C6—H6A | 0.9300 | C18—H18A | 0.9600 |
C7—C8 | 1.468 (9) | C18—H18B | 0.9600 |
C8—C9 | 1.272 (11) | C18—H18C | 0.9600 |
C8—H8A | 0.9300 | ||
C14—O2—C15 | 114.2 (6) | C13—C11—C12 | 119.1 (7) |
C6—C1—C2 | 116.5 (7) | C10—C11—C12 | 120.9 (7) |
C6—C1—C7 | 119.2 (7) | C11—C12—H12A | 109.5 |
C2—C1—C7 | 124.0 (6) | C11—C12—H12B | 109.5 |
C3—C2—C1 | 121.6 (7) | H12A—C12—H12B | 109.5 |
C3—C2—Cl1 | 119.0 (6) | C11—C12—H12C | 109.5 |
C1—C2—Cl1 | 119.3 (5) | H12A—C12—H12C | 109.5 |
C2—C3—C4 | 118.6 (7) | H12B—C12—H12C | 109.5 |
C2—C3—H3A | 120.7 | C11—C13—C14 | 119.2 (7) |
C4—C3—H3A | 120.7 | C11—C13—Cl3 | 122.3 (6) |
C5—C4—C3 | 121.2 (7) | C14—C13—Cl3 | 118.4 (5) |
C5—C4—Cl2 | 120.4 (7) | C16—C14—O2 | 122.2 (7) |
C3—C4—Cl2 | 118.3 (6) | C16—C14—C13 | 119.3 (6) |
C4—C5—C6 | 118.6 (8) | O2—C14—C13 | 118.5 (7) |
C4—C5—H5A | 120.7 | O2—C15—H15A | 109.5 |
C6—C5—H5A | 120.7 | O2—C15—H15B | 109.5 |
C5—C6—C1 | 123.1 (8) | H15A—C15—H15B | 109.5 |
C5—C6—H6A | 118.5 | O2—C15—H15C | 109.5 |
C1—C6—H6A | 118.5 | H15A—C15—H15C | 109.5 |
O1—C7—C8 | 121.2 (7) | H15B—C15—H15C | 109.5 |
O1—C7—C1 | 120.0 (6) | C14—C16—C17 | 122.5 (6) |
C8—C7—C1 | 118.6 (6) | C14—C16—Cl4 | 115.8 (5) |
C9—C8—C7 | 124.4 (7) | C17—C16—Cl4 | 121.7 (6) |
C9—C8—H8A | 117.8 | C10—C17—C16 | 117.7 (6) |
C7—C8—H8A | 117.8 | C10—C17—C18 | 122.7 (6) |
C8—C9—C10 | 129.2 (7) | C16—C17—C18 | 119.4 (7) |
C8—C9—H9A | 115.4 | C17—C18—H18A | 109.5 |
C10—C9—H9A | 115.4 | C17—C18—H18B | 109.5 |
C17—C10—C11 | 121.4 (6) | H18A—C18—H18B | 109.5 |
C17—C10—C9 | 120.8 (6) | C17—C18—H18C | 109.5 |
C11—C10—C9 | 117.7 (7) | H18A—C18—H18C | 109.5 |
C13—C11—C10 | 119.9 (7) | H18B—C18—H18C | 109.5 |
C6—C1—C2—C3 | 2.0 (11) | C17—C10—C11—C12 | 176.8 (7) |
C7—C1—C2—C3 | 175.8 (7) | C9—C10—C11—C12 | 0.2 (11) |
C6—C1—C2—Cl1 | −174.9 (6) | C10—C11—C13—C14 | −0.2 (11) |
C7—C1—C2—Cl1 | −1.1 (9) | C12—C11—C13—C14 | −177.7 (7) |
C1—C2—C3—C4 | 3.3 (11) | C10—C11—C13—Cl3 | −176.9 (6) |
Cl1—C2—C3—C4 | −179.8 (6) | C12—C11—C13—Cl3 | 5.6 (11) |
C2—C3—C4—C5 | −6.0 (12) | C15—O2—C14—C16 | −90.7 (9) |
C2—C3—C4—Cl2 | 177.4 (6) | C15—O2—C14—C13 | 91.6 (9) |
C3—C4—C5—C6 | 3.2 (13) | C11—C13—C14—C16 | 0.4 (11) |
Cl2—C4—C5—C6 | 179.8 (7) | Cl3—C13—C14—C16 | 177.2 (6) |
C4—C5—C6—C1 | 2.4 (14) | C11—C13—C14—O2 | 178.2 (7) |
C2—C1—C6—C5 | −5.0 (12) | Cl3—C13—C14—O2 | −5.0 (10) |
C7—C1—C6—C5 | −179.1 (8) | O2—C14—C16—C17 | −177.4 (7) |
C6—C1—C7—O1 | 45.5 (11) | C13—C14—C16—C17 | 0.3 (11) |
C2—C1—C7—O1 | −128.2 (9) | O2—C14—C16—Cl4 | 0.5 (9) |
C6—C1—C7—C8 | −129.2 (8) | C13—C14—C16—Cl4 | 178.2 (6) |
C2—C1—C7—C8 | 57.1 (10) | C11—C10—C17—C16 | 1.3 (11) |
O1—C7—C8—C9 | 2.3 (14) | C9—C10—C17—C16 | 177.8 (7) |
C1—C7—C8—C9 | 176.9 (8) | C11—C10—C17—C18 | 176.7 (7) |
C7—C8—C9—C10 | −178.3 (8) | C9—C10—C17—C18 | −6.8 (12) |
C8—C9—C10—C17 | −51.5 (13) | C14—C16—C17—C10 | −1.2 (11) |
C8—C9—C10—C11 | 125.1 (10) | Cl4—C16—C17—C10 | −178.9 (5) |
C17—C10—C11—C13 | −0.7 (11) | C14—C16—C17—C18 | −176.7 (7) |
C9—C10—C11—C13 | −177.2 (7) | Cl4—C16—C17—C18 | 5.5 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3A···O1i | 0.93 | 2.55 | 3.471 (11) | 170 |
Symmetry code: (i) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C18H14Cl4O2 |
Mr | 404.09 |
Crystal system, space group | Monoclinic, Pc |
Temperature (K) | 296 |
a, b, c (Å) | 7.8036 (4), 4.3526 (2), 26.6839 (11) |
β (°) | 97.020 (4) |
V (Å3) | 899.55 (7) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.67 |
Crystal size (mm) | 0.37 × 0.31 × 0.23 |
Data collection | |
Diffractometer | Oxford Diffraction Gemini R CCD |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2007) |
Tmin, Tmax | 0.502, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8039, 4142, 2501 |
Rint | 0.045 |
(sin θ/λ)max (Å−1) | 0.756 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.081, 0.239, 1.03 |
No. of reflections | 4142 |
No. of parameters | 221 |
No. of restraints | 2 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.80, −0.55 |
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 |
C3—H3A···O1i | 0.93 | 2.55 | 3.471 (11) | 169.9 |
Symmetry code: (i) x−1, y, z. |
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Chalcone is an unique template molecule that is associated with several biological activities. 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), antiherpes activity and antitumour activity and may be useful for the chemotherapy of leishmaniasis among others (Lawrence et al. 2001). Among several organic compounds reported to have NLO properties, chalcone derivatives are a 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). Structures of a few dichloro substituted chalcones viz., (2E)-1-(2,4-dichlorophenyl)-3-(quinolin-8-yl)prop-2-en-1-one (Sarojini et al. 2007), (2E)-1-(2,4-dichlorophenyl)-3-(4,5-dimethoxy-2-nitrophenyl) prop-2-en-1-one (Yathirajan, Mayekar, Narayana et al. 2007c), (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-(2-hydroxy-3-methoxyphenyl) prop-2-en-1-one (Yathirajan, Mayekar, Narayana et al. 2007a), (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 published. In continuation of our work on chalcones, a new chalcone C18H14Cl4O2 was synthesized and its crystal structure is reported.
The angle between the mean planes of the 3,5-dichloro-4-methoxy-2,6-dimethylphenyl and 2,4-dichlorophenyl groups is 47.6 (2)° (Fig. 1). The 4-methoxy group, with a C15–O2–C14–C13 torsion angle of 91.9 (9)°, is twisted away from the plane of the 3,5-dichloro-2,6-dimethylphenyl ring in an anti-clinal conformation. The ketone oxygen of the prop-2-en-1-one group is twisted in a syn-clinal conformation with the 2,4-dichlorophenyl group [C6–C1–C7–O1 torsion angle = 45.5 (11)°]. Crystal packing is stabilized by intermolecular C—H···O hydrogen bonding between the ketone oxygen from the prop-2-en-1-one group and a hydrogen atom from a nearby 2,4-dichlorophenyl group [C3–H3A···O1] which link the molecules into chains along the a axis of the unit cell (Fig. 2). Both of the 3,5-dichloro-4-methoxy-2,6-dimethylphenyl and 2,4-dichlorophenyl groups are aligned obliquely parallel to the ac face with the phenyl rings stacked obliquely along the b axis for both groups (Fig. 3).