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The title compound, C20H13Br3Cl2O2, arose unexpectedly as the product of a bromination reaction. The bromo substituents at the central C-C single bond are trans to each other [Br-C-C-Br = 178.53 (13)°] and the dihedral angle between the mean planes of the aromatic ring systems is 38.28 (10)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807015759/hb2359sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807015759/hb2359Isup2.hkl
Contains datablock I

CCDC reference: 647560

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.037
  • wR factor = 0.095
  • Data-to-parameter ratio = 22.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.06 PLAT431_ALERT_2_C Short Inter HL..A Contact Br1 .. Br2 .. 3.51 Ang. PLAT431_ALERT_2_C Short Inter HL..A Contact Br3 .. Cl1 .. 3.59 Ang.
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 1.062 Tmax scaled 0.279 Tmin scaled 0.251
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 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

Comment top

The title compound, (I), was obtained as an unexpected product in a bromination reaction. The expected compound was 2,3-dibromo-3-(6-methoxy-2-naphthyl)-1-(2,4-dichlorophenyl)propan-1-one which reacted further with excess bromine to form 2,3-dibromo-3-(5-bromo-6-methoxy-2-naphthyl)-1-(2,4-dichlorophenyl)propan-1-one.

A perspective view of (I) is shown in Fig. 1. Bond lengths and angles can be regarded as normal (Cambridge Crystallographic Database, Version 5.28, November 2006; updated January 2007; Mogul Version 1.1; Allen, 2002, Bruno et al., 2004). The bromo substituents at the central C—C single bond are trans to each other and the carbonyl group is is twisted by -41.1 (4)° out of the plane of the adjacent dichlorophenyl ring. The two aromatic ring systems are not coplanar [dihedral angle 38.28 (10)°].

For structures of related chalcones see Harrison et al. (2005, Butcher et al. (2006a,b) and Yathirajan et al. (2007).

Related literature top

For some recent crystal structures of related chalcones, see: Butcher, Yathirajan, Anilkumar et al. (2006); Butcher, Yathirajan, Sarojini et al. (2006); Harrison et al. (2005); Yathirajan et al. (2007); Allen (2002); Bruno et al. (2004).

Experimental top

(2E)-1-(2,4-Dichlorophenyl)-3-(6-methoxy-2-naphthyl)prop-2-en-1-one (3.57 g, 0.01 mol) was treated with bromine in acetic acid (30%) until the orange colour of the solution persisted. After stirring for half an hour, the contents were poured on to crushed ice. The resulting solid mass was collected by filtration. The compound was dried and recrystallized from ethanol. Crystals of (I) suitable for structure determination were obtained from acetone by slow evaporation (yield 80%; m.p. 439–441 K). Analysis for C20H13Br3Cl2O2: found (calculated): C 40.20 (40.31%); H 2.14 (2.20%).

Refinement top

The H atoms were found in a difference map, relocated in idealized locations (C—H = 0.95–1.00 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(Cmethyl). The methyl

group was allowed to rotate but not to tip to best fit the electron density.

Structure description top

The title compound, (I), was obtained as an unexpected product in a bromination reaction. The expected compound was 2,3-dibromo-3-(6-methoxy-2-naphthyl)-1-(2,4-dichlorophenyl)propan-1-one which reacted further with excess bromine to form 2,3-dibromo-3-(5-bromo-6-methoxy-2-naphthyl)-1-(2,4-dichlorophenyl)propan-1-one.

A perspective view of (I) is shown in Fig. 1. Bond lengths and angles can be regarded as normal (Cambridge Crystallographic Database, Version 5.28, November 2006; updated January 2007; Mogul Version 1.1; Allen, 2002, Bruno et al., 2004). The bromo substituents at the central C—C single bond are trans to each other and the carbonyl group is is twisted by -41.1 (4)° out of the plane of the adjacent dichlorophenyl ring. The two aromatic ring systems are not coplanar [dihedral angle 38.28 (10)°].

For structures of related chalcones see Harrison et al. (2005, Butcher et al. (2006a,b) and Yathirajan et al. (2007).

For some recent crystal structures of related chalcones, see: Butcher, Yathirajan, Anilkumar et al. (2006); Butcher, Yathirajan, Sarojini et al. (2006); Harrison et al. (2005); Yathirajan et al. (2007); Allen (2002); Bruno et al. (2004).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. Perspective view of (I) with the atom numbering; displacement ellipsoids are at the 50% probability level (arbitrary spheres for the H atoms).
2,3-Dibromo-3-(5-bromo-6-methoxy-2-naphthyl)-1-(2,4-dichlorophenyl)propan-1-one top
Crystal data top
C20H13Br3Cl2O2F(000) = 1152
Mr = 595.93Dx = 1.992 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 30108 reflections
a = 9.3506 (4) Åθ = 2.8–28.8°
b = 9.8861 (5) ŵ = 6.38 mm1
c = 21.7179 (9) ÅT = 173 K
β = 98.298 (3)°Block, light yellow
V = 1986.61 (16) Å30.23 × 0.22 × 0.20 mm
Z = 4
Data collection top
Stoe IPDSII two-circle
diffractometer
5563 independent reflections
Radiation source: fine-focus sealed tube4864 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.070
ω scansθmax = 29.7°, θmin = 2.8°
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
h = 1211
Tmin = 0.236, Tmax = 0.263k = 1313
30941 measured reflectionsl = 3030
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.095 w = 1/[σ2(Fo2) + (0.0473P)2 + 1.8115P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.002
5563 reflectionsΔρmax = 0.64 e Å3
246 parametersΔρmin = 0.75 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0064 (4)
Crystal data top
C20H13Br3Cl2O2V = 1986.61 (16) Å3
Mr = 595.93Z = 4
Monoclinic, P21/nMo Kα radiation
a = 9.3506 (4) ŵ = 6.38 mm1
b = 9.8861 (5) ÅT = 173 K
c = 21.7179 (9) Å0.23 × 0.22 × 0.20 mm
β = 98.298 (3)°
Data collection top
Stoe IPDSII two-circle
diffractometer
5563 independent reflections
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
4864 reflections with I > 2σ(I)
Tmin = 0.236, Tmax = 0.263Rint = 0.070
30941 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.095H-atom parameters constrained
S = 1.04Δρmax = 0.64 e Å3
5563 reflectionsΔρmin = 0.75 e Å3
246 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.8339 (3)1.0876 (2)0.72563 (10)0.0356 (5)
Cl11.12598 (8)0.97308 (8)0.78146 (3)0.03755 (17)
Cl21.03476 (9)0.81388 (8)1.00892 (3)0.03864 (17)
Br10.05973 (3)0.64021 (3)0.547822 (14)0.03635 (9)
Br20.74588 (3)0.79954 (3)0.654006 (13)0.03479 (9)
Br30.46605 (4)1.10035 (4)0.748535 (15)0.04018 (10)
C10.7893 (3)0.9882 (3)0.74980 (12)0.0291 (5)
C20.6601 (3)0.9090 (3)0.71527 (12)0.0293 (5)
H20.61690.84920.74480.035*
C30.5455 (3)1.0008 (3)0.68072 (13)0.0319 (6)
H30.59361.06720.65560.038*
C110.8542 (3)0.9380 (3)0.81242 (12)0.0286 (5)
C121.0039 (3)0.9343 (3)0.83201 (13)0.0291 (5)
C131.0609 (3)0.8940 (3)0.89222 (13)0.0325 (6)
H131.16240.88900.90470.039*
C140.9656 (3)0.8615 (3)0.93321 (13)0.0321 (6)
C150.8175 (3)0.8649 (3)0.91599 (13)0.0328 (6)
H150.75410.84230.94490.039*
C160.7638 (3)0.9019 (3)0.85572 (13)0.0316 (6)
H160.66210.90300.84330.038*
C210.4232 (3)0.9357 (3)0.63943 (13)0.0319 (6)
C220.3423 (4)0.8275 (3)0.66015 (14)0.0362 (6)
H220.36960.79160.70070.043*
C230.2261 (3)0.7744 (3)0.62292 (14)0.0343 (6)
H230.17310.70300.63830.041*
C240.1825 (3)0.8239 (3)0.56133 (12)0.0281 (5)
C250.2662 (3)0.9305 (3)0.53973 (12)0.0297 (5)
C260.3855 (3)0.9840 (3)0.57971 (13)0.0314 (6)
H260.44081.05470.56520.038*
C270.0616 (3)0.7750 (3)0.52019 (13)0.0293 (5)
C280.0269 (3)0.8237 (3)0.46020 (13)0.0305 (5)
C290.1124 (3)0.9287 (3)0.43966 (13)0.0338 (6)
H290.08930.96360.39870.041*
C300.2277 (3)0.9800 (3)0.47850 (13)0.0321 (6)
H300.28331.05060.46400.039*
O310.0872 (2)0.7671 (3)0.42291 (10)0.0377 (5)
C310.1160 (4)0.8144 (4)0.35984 (14)0.0421 (7)
H31A0.14270.91020.35960.063*
H31B0.19560.76200.33710.063*
H31C0.02930.80310.33980.063*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0350 (11)0.0367 (11)0.0352 (10)0.0030 (9)0.0054 (9)0.0042 (8)
Cl10.0301 (3)0.0462 (4)0.0379 (3)0.0003 (3)0.0102 (3)0.0037 (3)
Cl20.0445 (4)0.0410 (4)0.0282 (3)0.0026 (3)0.0020 (3)0.0026 (3)
Br10.03615 (17)0.03848 (17)0.03545 (15)0.00812 (12)0.00867 (12)0.00269 (11)
Br20.03989 (17)0.03451 (16)0.02969 (14)0.00460 (12)0.00409 (11)0.00076 (10)
Br30.03334 (17)0.0458 (2)0.04089 (17)0.00262 (13)0.00360 (12)0.01018 (13)
C10.0293 (14)0.0315 (13)0.0266 (11)0.0002 (11)0.0044 (10)0.0010 (10)
C20.0296 (13)0.0327 (14)0.0257 (11)0.0005 (11)0.0042 (10)0.0003 (10)
C30.0333 (15)0.0336 (14)0.0281 (12)0.0005 (11)0.0019 (10)0.0005 (10)
C110.0277 (13)0.0301 (13)0.0276 (11)0.0024 (10)0.0020 (10)0.0002 (10)
C120.0277 (13)0.0316 (13)0.0285 (12)0.0001 (11)0.0056 (10)0.0017 (10)
C130.0291 (14)0.0368 (15)0.0308 (13)0.0004 (11)0.0013 (11)0.0033 (11)
C140.0370 (15)0.0312 (14)0.0269 (12)0.0002 (11)0.0008 (11)0.0003 (10)
C150.0327 (14)0.0372 (15)0.0285 (12)0.0041 (12)0.0050 (11)0.0003 (11)
C160.0265 (13)0.0380 (15)0.0300 (12)0.0045 (11)0.0028 (10)0.0000 (11)
C210.0307 (14)0.0350 (14)0.0293 (12)0.0006 (11)0.0015 (10)0.0016 (11)
C220.0394 (16)0.0387 (15)0.0290 (12)0.0061 (13)0.0005 (11)0.0064 (11)
C230.0361 (15)0.0362 (15)0.0307 (13)0.0039 (12)0.0049 (11)0.0047 (11)
C240.0265 (13)0.0307 (13)0.0276 (11)0.0005 (10)0.0057 (10)0.0011 (10)
C250.0294 (13)0.0314 (13)0.0281 (12)0.0001 (11)0.0031 (10)0.0016 (10)
C260.0317 (14)0.0327 (14)0.0294 (12)0.0002 (11)0.0029 (11)0.0019 (10)
C270.0278 (13)0.0287 (13)0.0323 (12)0.0012 (10)0.0075 (10)0.0022 (10)
C280.0261 (13)0.0349 (14)0.0304 (12)0.0003 (11)0.0034 (10)0.0023 (10)
C290.0333 (15)0.0382 (15)0.0286 (12)0.0014 (12)0.0001 (11)0.0022 (11)
C300.0317 (15)0.0343 (14)0.0296 (12)0.0037 (11)0.0020 (11)0.0035 (11)
O310.0328 (11)0.0473 (13)0.0309 (10)0.0074 (10)0.0026 (8)0.0008 (9)
C310.0358 (17)0.058 (2)0.0304 (14)0.0039 (15)0.0031 (12)0.0013 (13)
Geometric parameters (Å, º) top
O1—C11.216 (4)C21—C261.380 (4)
Cl1—C121.737 (3)C21—C221.420 (4)
Cl2—C141.742 (3)C22—C231.363 (4)
Br1—C271.903 (3)C22—H220.9500
Br2—C21.973 (3)C23—C241.427 (4)
Br3—C32.002 (3)C23—H230.9500
C1—C111.492 (4)C24—C271.420 (4)
C1—C21.541 (4)C24—C251.432 (4)
C2—C31.517 (4)C25—C261.414 (4)
C2—H21.0000C25—C301.414 (4)
C3—C211.493 (4)C26—H260.9500
C3—H31.0000C27—C281.383 (4)
C11—C161.399 (4)C28—O311.364 (4)
C11—C121.403 (4)C28—C291.421 (4)
C12—C131.397 (4)C29—C301.367 (4)
C13—C141.385 (4)C29—H290.9500
C13—H130.9500C30—H300.9500
C14—C151.382 (4)O31—C311.436 (4)
C15—C161.382 (4)C31—H31A0.9800
C15—H150.9500C31—H31B0.9800
C16—H160.9500C31—H31C0.9800
O1—C1—C11122.9 (3)C22—C21—C3122.1 (3)
O1—C1—C2119.6 (3)C23—C22—C21121.2 (3)
C11—C1—C2117.5 (2)C23—C22—H22119.4
C3—C2—C1112.7 (2)C21—C22—H22119.4
C3—C2—Br2108.74 (18)C22—C23—C24121.3 (3)
C1—C2—Br2103.92 (18)C22—C23—H23119.4
C3—C2—H2110.4C24—C23—H23119.4
C1—C2—H2110.4C27—C24—C23124.5 (3)
Br2—C2—H2110.4C27—C24—C25117.9 (2)
C21—C3—C2117.6 (3)C23—C24—C25117.6 (3)
C21—C3—Br3108.7 (2)C26—C25—C30121.3 (3)
C2—C3—Br3103.93 (18)C26—C25—C24119.7 (2)
C21—C3—H3108.7C30—C25—C24119.1 (3)
C2—C3—H3108.7C21—C26—C25121.3 (3)
Br3—C3—H3108.7C21—C26—H26119.3
C16—C11—C12117.6 (3)C25—C26—H26119.3
C16—C11—C1119.5 (3)C28—C27—C24122.1 (3)
C12—C11—C1122.8 (2)C28—C27—Br1118.1 (2)
C13—C12—C11121.3 (3)C24—C27—Br1119.8 (2)
C13—C12—Cl1117.2 (2)O31—C28—C27118.3 (3)
C11—C12—Cl1121.4 (2)O31—C28—C29122.8 (3)
C14—C13—C12118.3 (3)C27—C28—C29119.0 (3)
C14—C13—H13120.8C30—C29—C28120.4 (3)
C12—C13—H13120.8C30—C29—H29119.8
C15—C14—C13122.2 (3)C28—C29—H29119.8
C15—C14—Cl2118.9 (2)C29—C30—C25121.5 (3)
C13—C14—Cl2118.9 (2)C29—C30—H30119.2
C16—C15—C14118.4 (3)C25—C30—H30119.2
C16—C15—H15120.8C28—O31—C31117.1 (2)
C14—C15—H15120.8O31—C31—H31A109.5
C15—C16—C11122.2 (3)O31—C31—H31B109.5
C15—C16—H16118.9H31A—C31—H31B109.5
C11—C16—H16118.9O31—C31—H31C109.5
C26—C21—C22118.9 (3)H31A—C31—H31C109.5
C26—C21—C3119.0 (3)H31B—C31—H31C109.5
O1—C1—C2—C338.8 (4)C26—C21—C22—C232.2 (5)
C11—C1—C2—C3141.1 (3)C3—C21—C22—C23176.4 (3)
O1—C1—C2—Br278.7 (3)C21—C22—C23—C240.9 (5)
C11—C1—C2—Br2101.3 (2)C22—C23—C24—C27179.1 (3)
C1—C2—C3—C21173.0 (2)C22—C23—C24—C250.7 (5)
Br2—C2—C3—C2158.4 (3)C27—C24—C25—C26178.6 (3)
C1—C2—C3—Br366.8 (2)C23—C24—C25—C261.1 (4)
Br2—C2—C3—Br3178.53 (13)C27—C24—C25—C301.5 (4)
O1—C1—C11—C16134.0 (3)C23—C24—C25—C30178.7 (3)
C2—C1—C11—C1646.0 (4)C22—C21—C26—C251.7 (5)
O1—C1—C11—C1241.1 (4)C3—C21—C26—C25176.9 (3)
C2—C1—C11—C12138.9 (3)C30—C25—C26—C21179.9 (3)
C16—C11—C12—C131.1 (4)C24—C25—C26—C210.1 (5)
C1—C11—C12—C13176.3 (3)C23—C24—C27—C28177.9 (3)
C16—C11—C12—Cl1178.4 (2)C25—C24—C27—C282.4 (4)
C1—C11—C12—Cl16.4 (4)C23—C24—C27—Br13.1 (4)
C11—C12—C13—C142.0 (4)C25—C24—C27—Br1176.7 (2)
Cl1—C12—C13—C14179.5 (2)C24—C27—C28—O31177.2 (3)
C12—C13—C14—C151.4 (5)Br1—C27—C28—O313.8 (4)
C12—C13—C14—Cl2178.9 (2)C24—C27—C28—C291.9 (4)
C13—C14—C15—C160.1 (5)Br1—C27—C28—C29177.2 (2)
Cl2—C14—C15—C16179.6 (2)O31—C28—C29—C30178.5 (3)
C14—C15—C16—C111.1 (5)C27—C28—C29—C300.5 (5)
C12—C11—C16—C150.5 (5)C28—C29—C30—C250.3 (5)
C1—C11—C16—C15174.8 (3)C26—C25—C30—C29179.9 (3)
C2—C3—C21—C26131.5 (3)C24—C25—C30—C290.2 (5)
Br3—C3—C21—C26110.8 (3)C27—C28—O31—C31176.7 (3)
C2—C3—C21—C2250.0 (4)C29—C28—O31—C312.3 (4)
Br3—C3—C21—C2267.7 (3)

Experimental details

Crystal data
Chemical formulaC20H13Br3Cl2O2
Mr595.93
Crystal system, space groupMonoclinic, P21/n
Temperature (K)173
a, b, c (Å)9.3506 (4), 9.8861 (5), 21.7179 (9)
β (°) 98.298 (3)
V3)1986.61 (16)
Z4
Radiation typeMo Kα
µ (mm1)6.38
Crystal size (mm)0.23 × 0.22 × 0.20
Data collection
DiffractometerStoe IPDSII two-circle
Absorption correctionMulti-scan
(MULABS; Spek, 2003; Blessing, 1995)
Tmin, Tmax0.236, 0.263
No. of measured, independent and
observed [I > 2σ(I)] reflections
30941, 5563, 4864
Rint0.070
(sin θ/λ)max1)0.698
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.095, 1.04
No. of reflections5563
No. of parameters246
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.64, 0.75

Computer programs: X-AREA (Stoe & Cie, 2001), X-AREA, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97.

Selected torsion angles (º) top
Br2—C2—C3—Br3178.53 (13)O1—C1—C11—C1241.1 (4)
 

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