Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807015759/hb2359sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807015759/hb2359Isup2.hkl |
CCDC reference: 647560
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (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
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).
(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%).
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.
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).
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.
Fig. 1. Perspective view of (I) with the atom numbering; displacement ellipsoids are at the 50% probability level (arbitrary spheres for the H atoms). |
C20H13Br3Cl2O2 | F(000) = 1152 |
Mr = 595.93 | Dx = 1.992 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 30108 reflections |
a = 9.3506 (4) Å | θ = 2.8–28.8° |
b = 9.8861 (5) Å | µ = 6.38 mm−1 |
c = 21.7179 (9) Å | T = 173 K |
β = 98.298 (3)° | Block, light yellow |
V = 1986.61 (16) Å3 | 0.23 × 0.22 × 0.20 mm |
Z = 4 |
Stoe IPDSII two-circle diffractometer | 5563 independent reflections |
Radiation source: fine-focus sealed tube | 4864 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.070 |
ω scans | θmax = 29.7°, θmin = 2.8° |
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) | h = −12→11 |
Tmin = 0.236, Tmax = 0.263 | k = −13→13 |
30941 measured reflections | l = −30→30 |
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)] = 0.037 | H-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 reflections | Δρmax = 0.64 e Å−3 |
246 parameters | Δρmin = −0.75 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0064 (4) |
C20H13Br3Cl2O2 | V = 1986.61 (16) Å3 |
Mr = 595.93 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.3506 (4) Å | µ = 6.38 mm−1 |
b = 9.8861 (5) Å | T = 173 K |
c = 21.7179 (9) Å | 0.23 × 0.22 × 0.20 mm |
β = 98.298 (3)° |
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 = 0.263 | Rint = 0.070 |
30941 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.095 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.64 e Å−3 |
5563 reflections | Δρmin = −0.75 e Å−3 |
246 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 | ||
O1 | 0.8339 (3) | 1.0876 (2) | 0.72563 (10) | 0.0356 (5) | |
Cl1 | 1.12598 (8) | 0.97308 (8) | 0.78146 (3) | 0.03755 (17) | |
Cl2 | 1.03476 (9) | 0.81388 (8) | 1.00892 (3) | 0.03864 (17) | |
Br1 | −0.05973 (3) | 0.64021 (3) | 0.547822 (14) | 0.03635 (9) | |
Br2 | 0.74588 (3) | 0.79954 (3) | 0.654006 (13) | 0.03479 (9) | |
Br3 | 0.46605 (4) | 1.10035 (4) | 0.748535 (15) | 0.04018 (10) | |
C1 | 0.7893 (3) | 0.9882 (3) | 0.74980 (12) | 0.0291 (5) | |
C2 | 0.6601 (3) | 0.9090 (3) | 0.71527 (12) | 0.0293 (5) | |
H2 | 0.6169 | 0.8492 | 0.7448 | 0.035* | |
C3 | 0.5455 (3) | 1.0008 (3) | 0.68072 (13) | 0.0319 (6) | |
H3 | 0.5936 | 1.0672 | 0.6556 | 0.038* | |
C11 | 0.8542 (3) | 0.9380 (3) | 0.81242 (12) | 0.0286 (5) | |
C12 | 1.0039 (3) | 0.9343 (3) | 0.83201 (13) | 0.0291 (5) | |
C13 | 1.0609 (3) | 0.8940 (3) | 0.89222 (13) | 0.0325 (6) | |
H13 | 1.1624 | 0.8890 | 0.9047 | 0.039* | |
C14 | 0.9656 (3) | 0.8615 (3) | 0.93321 (13) | 0.0321 (6) | |
C15 | 0.8175 (3) | 0.8649 (3) | 0.91599 (13) | 0.0328 (6) | |
H15 | 0.7541 | 0.8423 | 0.9449 | 0.039* | |
C16 | 0.7638 (3) | 0.9019 (3) | 0.85572 (13) | 0.0316 (6) | |
H16 | 0.6621 | 0.9030 | 0.8433 | 0.038* | |
C21 | 0.4232 (3) | 0.9357 (3) | 0.63943 (13) | 0.0319 (6) | |
C22 | 0.3423 (4) | 0.8275 (3) | 0.66015 (14) | 0.0362 (6) | |
H22 | 0.3696 | 0.7916 | 0.7007 | 0.043* | |
C23 | 0.2261 (3) | 0.7744 (3) | 0.62292 (14) | 0.0343 (6) | |
H23 | 0.1731 | 0.7030 | 0.6383 | 0.041* | |
C24 | 0.1825 (3) | 0.8239 (3) | 0.56133 (12) | 0.0281 (5) | |
C25 | 0.2662 (3) | 0.9305 (3) | 0.53973 (12) | 0.0297 (5) | |
C26 | 0.3855 (3) | 0.9840 (3) | 0.57971 (13) | 0.0314 (6) | |
H26 | 0.4408 | 1.0547 | 0.5652 | 0.038* | |
C27 | 0.0616 (3) | 0.7750 (3) | 0.52019 (13) | 0.0293 (5) | |
C28 | 0.0269 (3) | 0.8237 (3) | 0.46020 (13) | 0.0305 (5) | |
C29 | 0.1124 (3) | 0.9287 (3) | 0.43966 (13) | 0.0338 (6) | |
H29 | 0.0893 | 0.9636 | 0.3987 | 0.041* | |
C30 | 0.2277 (3) | 0.9800 (3) | 0.47850 (13) | 0.0321 (6) | |
H30 | 0.2833 | 1.0506 | 0.4640 | 0.039* | |
O31 | −0.0872 (2) | 0.7671 (3) | 0.42291 (10) | 0.0377 (5) | |
C31 | −0.1160 (4) | 0.8144 (4) | 0.35984 (14) | 0.0421 (7) | |
H31A | −0.1427 | 0.9102 | 0.3596 | 0.063* | |
H31B | −0.1956 | 0.7620 | 0.3371 | 0.063* | |
H31C | −0.0293 | 0.8031 | 0.3398 | 0.063* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0350 (11) | 0.0367 (11) | 0.0352 (10) | −0.0030 (9) | 0.0054 (9) | 0.0042 (8) |
Cl1 | 0.0301 (3) | 0.0462 (4) | 0.0379 (3) | −0.0003 (3) | 0.0102 (3) | 0.0037 (3) |
Cl2 | 0.0445 (4) | 0.0410 (4) | 0.0282 (3) | 0.0026 (3) | −0.0020 (3) | 0.0026 (3) |
Br1 | 0.03615 (17) | 0.03848 (17) | 0.03545 (15) | −0.00812 (12) | 0.00867 (12) | −0.00269 (11) |
Br2 | 0.03989 (17) | 0.03451 (16) | 0.02969 (14) | 0.00460 (12) | 0.00409 (11) | −0.00076 (10) |
Br3 | 0.03334 (17) | 0.0458 (2) | 0.04089 (17) | 0.00262 (13) | 0.00360 (12) | −0.01018 (13) |
C1 | 0.0293 (14) | 0.0315 (13) | 0.0266 (11) | 0.0002 (11) | 0.0044 (10) | −0.0010 (10) |
C2 | 0.0296 (13) | 0.0327 (14) | 0.0257 (11) | 0.0005 (11) | 0.0042 (10) | −0.0003 (10) |
C3 | 0.0333 (15) | 0.0336 (14) | 0.0281 (12) | 0.0005 (11) | 0.0019 (10) | −0.0005 (10) |
C11 | 0.0277 (13) | 0.0301 (13) | 0.0276 (11) | −0.0024 (10) | 0.0020 (10) | −0.0002 (10) |
C12 | 0.0277 (13) | 0.0316 (13) | 0.0285 (12) | 0.0001 (11) | 0.0056 (10) | −0.0017 (10) |
C13 | 0.0291 (14) | 0.0368 (15) | 0.0308 (13) | 0.0004 (11) | 0.0013 (11) | −0.0033 (11) |
C14 | 0.0370 (15) | 0.0312 (14) | 0.0269 (12) | 0.0002 (11) | 0.0008 (11) | −0.0003 (10) |
C15 | 0.0327 (14) | 0.0372 (15) | 0.0285 (12) | −0.0041 (12) | 0.0050 (11) | 0.0003 (11) |
C16 | 0.0265 (13) | 0.0380 (15) | 0.0300 (12) | −0.0045 (11) | 0.0028 (10) | 0.0000 (11) |
C21 | 0.0307 (14) | 0.0350 (14) | 0.0293 (12) | −0.0006 (11) | 0.0015 (10) | 0.0016 (11) |
C22 | 0.0394 (16) | 0.0387 (15) | 0.0290 (12) | −0.0061 (13) | −0.0005 (11) | 0.0064 (11) |
C23 | 0.0361 (15) | 0.0362 (15) | 0.0307 (13) | −0.0039 (12) | 0.0049 (11) | 0.0047 (11) |
C24 | 0.0265 (13) | 0.0307 (13) | 0.0276 (11) | 0.0005 (10) | 0.0057 (10) | 0.0011 (10) |
C25 | 0.0294 (13) | 0.0314 (13) | 0.0281 (12) | 0.0001 (11) | 0.0031 (10) | 0.0016 (10) |
C26 | 0.0317 (14) | 0.0327 (14) | 0.0294 (12) | −0.0002 (11) | 0.0029 (11) | 0.0019 (10) |
C27 | 0.0278 (13) | 0.0287 (13) | 0.0323 (12) | −0.0012 (10) | 0.0075 (10) | −0.0022 (10) |
C28 | 0.0261 (13) | 0.0349 (14) | 0.0304 (12) | 0.0003 (11) | 0.0034 (10) | −0.0023 (10) |
C29 | 0.0333 (15) | 0.0382 (15) | 0.0286 (12) | 0.0014 (12) | 0.0001 (11) | 0.0022 (11) |
C30 | 0.0317 (15) | 0.0343 (14) | 0.0296 (12) | −0.0037 (11) | 0.0020 (11) | 0.0035 (11) |
O31 | 0.0328 (11) | 0.0473 (13) | 0.0309 (10) | −0.0074 (10) | −0.0026 (8) | 0.0008 (9) |
C31 | 0.0358 (17) | 0.058 (2) | 0.0304 (14) | −0.0039 (15) | −0.0031 (12) | 0.0013 (13) |
O1—C1 | 1.216 (4) | C21—C26 | 1.380 (4) |
Cl1—C12 | 1.737 (3) | C21—C22 | 1.420 (4) |
Cl2—C14 | 1.742 (3) | C22—C23 | 1.363 (4) |
Br1—C27 | 1.903 (3) | C22—H22 | 0.9500 |
Br2—C2 | 1.973 (3) | C23—C24 | 1.427 (4) |
Br3—C3 | 2.002 (3) | C23—H23 | 0.9500 |
C1—C11 | 1.492 (4) | C24—C27 | 1.420 (4) |
C1—C2 | 1.541 (4) | C24—C25 | 1.432 (4) |
C2—C3 | 1.517 (4) | C25—C26 | 1.414 (4) |
C2—H2 | 1.0000 | C25—C30 | 1.414 (4) |
C3—C21 | 1.493 (4) | C26—H26 | 0.9500 |
C3—H3 | 1.0000 | C27—C28 | 1.383 (4) |
C11—C16 | 1.399 (4) | C28—O31 | 1.364 (4) |
C11—C12 | 1.403 (4) | C28—C29 | 1.421 (4) |
C12—C13 | 1.397 (4) | C29—C30 | 1.367 (4) |
C13—C14 | 1.385 (4) | C29—H29 | 0.9500 |
C13—H13 | 0.9500 | C30—H30 | 0.9500 |
C14—C15 | 1.382 (4) | O31—C31 | 1.436 (4) |
C15—C16 | 1.382 (4) | C31—H31A | 0.9800 |
C15—H15 | 0.9500 | C31—H31B | 0.9800 |
C16—H16 | 0.9500 | C31—H31C | 0.9800 |
O1—C1—C11 | 122.9 (3) | C22—C21—C3 | 122.1 (3) |
O1—C1—C2 | 119.6 (3) | C23—C22—C21 | 121.2 (3) |
C11—C1—C2 | 117.5 (2) | C23—C22—H22 | 119.4 |
C3—C2—C1 | 112.7 (2) | C21—C22—H22 | 119.4 |
C3—C2—Br2 | 108.74 (18) | C22—C23—C24 | 121.3 (3) |
C1—C2—Br2 | 103.92 (18) | C22—C23—H23 | 119.4 |
C3—C2—H2 | 110.4 | C24—C23—H23 | 119.4 |
C1—C2—H2 | 110.4 | C27—C24—C23 | 124.5 (3) |
Br2—C2—H2 | 110.4 | C27—C24—C25 | 117.9 (2) |
C21—C3—C2 | 117.6 (3) | C23—C24—C25 | 117.6 (3) |
C21—C3—Br3 | 108.7 (2) | C26—C25—C30 | 121.3 (3) |
C2—C3—Br3 | 103.93 (18) | C26—C25—C24 | 119.7 (2) |
C21—C3—H3 | 108.7 | C30—C25—C24 | 119.1 (3) |
C2—C3—H3 | 108.7 | C21—C26—C25 | 121.3 (3) |
Br3—C3—H3 | 108.7 | C21—C26—H26 | 119.3 |
C16—C11—C12 | 117.6 (3) | C25—C26—H26 | 119.3 |
C16—C11—C1 | 119.5 (3) | C28—C27—C24 | 122.1 (3) |
C12—C11—C1 | 122.8 (2) | C28—C27—Br1 | 118.1 (2) |
C13—C12—C11 | 121.3 (3) | C24—C27—Br1 | 119.8 (2) |
C13—C12—Cl1 | 117.2 (2) | O31—C28—C27 | 118.3 (3) |
C11—C12—Cl1 | 121.4 (2) | O31—C28—C29 | 122.8 (3) |
C14—C13—C12 | 118.3 (3) | C27—C28—C29 | 119.0 (3) |
C14—C13—H13 | 120.8 | C30—C29—C28 | 120.4 (3) |
C12—C13—H13 | 120.8 | C30—C29—H29 | 119.8 |
C15—C14—C13 | 122.2 (3) | C28—C29—H29 | 119.8 |
C15—C14—Cl2 | 118.9 (2) | C29—C30—C25 | 121.5 (3) |
C13—C14—Cl2 | 118.9 (2) | C29—C30—H30 | 119.2 |
C16—C15—C14 | 118.4 (3) | C25—C30—H30 | 119.2 |
C16—C15—H15 | 120.8 | C28—O31—C31 | 117.1 (2) |
C14—C15—H15 | 120.8 | O31—C31—H31A | 109.5 |
C15—C16—C11 | 122.2 (3) | O31—C31—H31B | 109.5 |
C15—C16—H16 | 118.9 | H31A—C31—H31B | 109.5 |
C11—C16—H16 | 118.9 | O31—C31—H31C | 109.5 |
C26—C21—C22 | 118.9 (3) | H31A—C31—H31C | 109.5 |
C26—C21—C3 | 119.0 (3) | H31B—C31—H31C | 109.5 |
O1—C1—C2—C3 | −38.8 (4) | C26—C21—C22—C23 | −2.2 (5) |
C11—C1—C2—C3 | 141.1 (3) | C3—C21—C22—C23 | 176.4 (3) |
O1—C1—C2—Br2 | 78.7 (3) | C21—C22—C23—C24 | 0.9 (5) |
C11—C1—C2—Br2 | −101.3 (2) | C22—C23—C24—C27 | −179.1 (3) |
C1—C2—C3—C21 | 173.0 (2) | C22—C23—C24—C25 | 0.7 (5) |
Br2—C2—C3—C21 | 58.4 (3) | C27—C24—C25—C26 | 178.6 (3) |
C1—C2—C3—Br3 | −66.8 (2) | C23—C24—C25—C26 | −1.1 (4) |
Br2—C2—C3—Br3 | 178.53 (13) | C27—C24—C25—C30 | −1.5 (4) |
O1—C1—C11—C16 | 134.0 (3) | C23—C24—C25—C30 | 178.7 (3) |
C2—C1—C11—C16 | −46.0 (4) | C22—C21—C26—C25 | 1.7 (5) |
O1—C1—C11—C12 | −41.1 (4) | C3—C21—C26—C25 | −176.9 (3) |
C2—C1—C11—C12 | 138.9 (3) | C30—C25—C26—C21 | −179.9 (3) |
C16—C11—C12—C13 | 1.1 (4) | C24—C25—C26—C21 | −0.1 (5) |
C1—C11—C12—C13 | 176.3 (3) | C23—C24—C27—C28 | −177.9 (3) |
C16—C11—C12—Cl1 | 178.4 (2) | C25—C24—C27—C28 | 2.4 (4) |
C1—C11—C12—Cl1 | −6.4 (4) | C23—C24—C27—Br1 | 3.1 (4) |
C11—C12—C13—C14 | −2.0 (4) | C25—C24—C27—Br1 | −176.7 (2) |
Cl1—C12—C13—C14 | −179.5 (2) | C24—C27—C28—O31 | 177.2 (3) |
C12—C13—C14—C15 | 1.4 (5) | Br1—C27—C28—O31 | −3.8 (4) |
C12—C13—C14—Cl2 | −178.9 (2) | C24—C27—C28—C29 | −1.9 (4) |
C13—C14—C15—C16 | 0.1 (5) | Br1—C27—C28—C29 | 177.2 (2) |
Cl2—C14—C15—C16 | −179.6 (2) | O31—C28—C29—C30 | −178.5 (3) |
C14—C15—C16—C11 | −1.1 (5) | C27—C28—C29—C30 | 0.5 (5) |
C12—C11—C16—C15 | 0.5 (5) | C28—C29—C30—C25 | 0.3 (5) |
C1—C11—C16—C15 | −174.8 (3) | C26—C25—C30—C29 | −179.9 (3) |
C2—C3—C21—C26 | −131.5 (3) | C24—C25—C30—C29 | 0.2 (5) |
Br3—C3—C21—C26 | 110.8 (3) | C27—C28—O31—C31 | −176.7 (3) |
C2—C3—C21—C22 | 50.0 (4) | C29—C28—O31—C31 | 2.3 (4) |
Br3—C3—C21—C22 | −67.7 (3) |
Experimental details
Crystal data | |
Chemical formula | C20H13Br3Cl2O2 |
Mr | 595.93 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 173 |
a, b, c (Å) | 9.3506 (4), 9.8861 (5), 21.7179 (9) |
β (°) | 98.298 (3) |
V (Å3) | 1986.61 (16) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 6.38 |
Crystal size (mm) | 0.23 × 0.22 × 0.20 |
Data collection | |
Diffractometer | Stoe IPDSII two-circle |
Absorption correction | Multi-scan (MULABS; Spek, 2003; Blessing, 1995) |
Tmin, Tmax | 0.236, 0.263 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 30941, 5563, 4864 |
Rint | 0.070 |
(sin θ/λ)max (Å−1) | 0.698 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.095, 1.04 |
No. of reflections | 5563 |
No. of parameters | 246 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.64, −0.75 |
Computer programs: X-AREA (Stoe & Cie, 2001), X-AREA, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97.
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
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).