Related literature
For related structures and background references, see: Li et al. (2009a
,b
).
Experimental
Crystal data
C26H22Cl2O4 Mr = 469.34 Monoclinic, P 21 /c a = 14.2156 (4) Å b = 5.8647 (2) Å c = 27.3752 (9) Å β = 94.840 (2)° V = 2274.14 (13) Å3 Z = 4 Mo Kα radiation μ = 0.32 mm−1 T = 120 K 0.20 × 0.10 × 0.07 mm
|
Data collection
Nonius KappaCCD diffractometer 24499 measured reflections 5209 independent reflections 3171 reflections with I > 2σ(I) Rint = 0.081
|
D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A | C6—H6⋯O1i | 0.95 | 2.49 | 3.411 (4) | 164 | C8—H8A⋯O4ii | 0.99 | 2.52 | 3.388 (4) | 146 | C8—H8B⋯Cl2 | 0.99 | 2.69 | 3.365 (3) | 125 | C12—H12⋯O1iii | 0.95 | 2.42 | 3.354 (4) | 168 | C14—H14⋯O4ii | 0.95 | 2.33 | 3.270 (4) | 170 | C17—H17⋯Cl1iv | 0.95 | 2.76 | 3.635 (3) | 153 | Symmetry codes: (i) -x, -y+2, -z; (ii) x, y+1, z; (iii) -x, -y+1, -z; (iv) . | |
Data collection: COLLECT (Nonius, 1998
); cell refinement: SCALEPACK (Otwinowski & Minor, 1997
); data reduction: DENZO (Otwinowski & Minor 1997
), SCALEPACK and SORTAV (Blessing, 1995
); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008
); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008
); molecular graphics: ORTEP-3 (Farrugia, 1997
); software used to prepare material for publication: SHELXL97.
Supporting information
(2E)-1-(2,4-Dichlorophenyl)-3-(6-methoxy-2-naphthyl)prop-2-en-1-one (1.8 g, 5 mmol) and ethyl acetoacetate (0.65 g, 5 mmol) were refluxed for 4 hr in 15 ml of ethanol in the presence of 0.8 ml 10% NaOH. The mixture was cooled to room temperature and the reaction mass was filtered and recrystallized using acetonitrile to yield colourless blocks of (I) (m.p.: 393–395 K).
The hydrogen atoms were geometrically placed (C—H = 0.95–1.00 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C). A rotating rigid-group model was applied to the methyl group.
Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor 1997), and SORTAV (Blessing, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
Ethyl 4-(2,4-dichlorophenyl)-6-(6-methoxy-2-naphthyl)-2-oxocyclohex-3-ene- 1-carboxylate
top Crystal data top C26H22Cl2O4 | F(000) = 976 |
Mr = 469.34 | Dx = 1.371 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 19625 reflections |
a = 14.2156 (4) Å | θ = 2.9–27.5° |
b = 5.8647 (2) Å | µ = 0.32 mm−1 |
c = 27.3752 (9) Å | T = 120 K |
β = 94.840 (2)° | Block, colourless |
V = 2274.14 (13) Å3 | 0.20 × 0.10 × 0.07 mm |
Z = 4 | |
Data collection top Nonius KappaCCD diffractometer | 3171 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.081 |
Graphite monochromator | θmax = 27.5°, θmin = 3.1° |
ω and ϕ scans | h = −18→18 |
24499 measured reflections | k = −7→7 |
5209 independent reflections | l = −35→35 |
Refinement top 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)] = 0.062 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.160 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0569P)2 + 1.4128P] where P = (Fo2 + 2Fc2)/3 |
5209 reflections | (Δ/σ)max < 0.001 |
291 parameters | Δρmax = 0.39 e Å−3 |
0 restraints | Δρmin = −0.32 e Å−3 |
Crystal data top C26H22Cl2O4 | V = 2274.14 (13) Å3 |
Mr = 469.34 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 14.2156 (4) Å | µ = 0.32 mm−1 |
b = 5.8647 (2) Å | T = 120 K |
c = 27.3752 (9) Å | 0.20 × 0.10 × 0.07 mm |
β = 94.840 (2)° | |
Data collection top Nonius KappaCCD diffractometer | 3171 reflections with I > 2σ(I) |
24499 measured reflections | Rint = 0.081 |
5209 independent reflections | |
Refinement top R[F2 > 2σ(F2)] = 0.062 | 0 restraints |
wR(F2) = 0.160 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.39 e Å−3 |
5209 reflections | Δρmin = −0.32 e Å−3 |
291 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 | x | y | z | Uiso*/Ueq | |
C1 | 0.2743 (2) | 1.2107 (5) | −0.05812 (11) | 0.0325 (7) | |
C2 | 0.3364 (2) | 1.0439 (5) | −0.04033 (11) | 0.0317 (7) | |
H2 | 0.3962 | 1.0277 | −0.0530 | 0.038* | |
C3 | 0.3101 (2) | 0.9003 (5) | −0.00372 (10) | 0.0271 (7) | |
C4 | 0.2229 (2) | 0.9190 (5) | 0.01610 (10) | 0.0268 (7) | |
C5 | 0.1630 (2) | 1.0922 (6) | −0.00319 (11) | 0.0337 (8) | |
H5 | 0.1031 | 1.1100 | 0.0093 | 0.040* | |
C6 | 0.1876 (2) | 1.2388 (6) | −0.03978 (12) | 0.0364 (8) | |
H6 | 0.1457 | 1.3558 | −0.0519 | 0.044* | |
C7 | 0.18917 (19) | 0.7672 (5) | 0.05408 (10) | 0.0256 (7) | |
C8 | 0.2417 (2) | 0.7606 (5) | 0.10417 (10) | 0.0279 (7) | |
H8A | 0.2294 | 0.9038 | 0.1217 | 0.033* | |
H8B | 0.3103 | 0.7529 | 0.1005 | 0.033* | |
C9 | 0.21375 (19) | 0.5572 (5) | 0.13528 (10) | 0.0272 (7) | |
H9 | 0.2380 | 0.4157 | 0.1203 | 0.033* | |
C10 | 0.10628 (19) | 0.5373 (6) | 0.13368 (11) | 0.0304 (7) | |
H10 | 0.0810 | 0.6780 | 0.1486 | 0.036* | |
C11 | 0.0638 (2) | 0.5189 (6) | 0.08069 (11) | 0.0312 (7) | |
C12 | 0.1079 (2) | 0.6548 (5) | 0.04425 (11) | 0.0311 (7) | |
H12 | 0.0774 | 0.6639 | 0.0121 | 0.037* | |
C13 | 0.26075 (19) | 0.5753 (5) | 0.18738 (10) | 0.0256 (7) | |
C14 | 0.24668 (19) | 0.7727 (5) | 0.21574 (10) | 0.0274 (7) | |
H14 | 0.2040 | 0.8869 | 0.2031 | 0.033* | |
C15 | 0.29374 (19) | 0.8015 (5) | 0.26125 (10) | 0.0249 (6) | |
H15 | 0.2819 | 0.9335 | 0.2799 | 0.030* | |
C16 | 0.35953 (18) | 0.6376 (5) | 0.28076 (9) | 0.0203 (6) | |
C17 | 0.41590 (18) | 0.6728 (5) | 0.32532 (10) | 0.0220 (6) | |
H17 | 0.4088 | 0.8083 | 0.3437 | 0.026* | |
C18 | 0.48025 (19) | 0.5124 (5) | 0.34184 (10) | 0.0232 (6) | |
C19 | 0.49063 (19) | 0.3078 (5) | 0.31567 (10) | 0.0239 (6) | |
H19 | 0.5351 | 0.1965 | 0.3280 | 0.029* | |
C20 | 0.43709 (19) | 0.2697 (5) | 0.27280 (10) | 0.0237 (6) | |
H20 | 0.4443 | 0.1311 | 0.2556 | 0.028* | |
C21 | 0.37076 (18) | 0.4340 (5) | 0.25358 (10) | 0.0213 (6) | |
C22 | 0.31971 (19) | 0.4083 (5) | 0.20690 (10) | 0.0235 (6) | |
H22 | 0.3267 | 0.2719 | 0.1889 | 0.028* | |
C23 | 0.5480 (2) | 0.7485 (5) | 0.40688 (11) | 0.0318 (7) | |
H23A | 0.5984 | 0.7451 | 0.4336 | 0.048* | |
H23B | 0.4879 | 0.7852 | 0.4202 | 0.048* | |
H23C | 0.5624 | 0.8647 | 0.3829 | 0.048* | |
C24 | 0.0723 (2) | 0.3334 (6) | 0.16028 (11) | 0.0324 (7) | |
C25 | −0.0480 (3) | 0.1826 (8) | 0.20559 (15) | 0.0657 (12) | |
H25A | −0.0850 | 0.2342 | 0.2326 | 0.079* | |
H25B | 0.0014 | 0.0764 | 0.2195 | 0.079* | |
C26 | −0.1126 (3) | 0.0587 (8) | 0.16739 (18) | 0.0768 (14) | |
H26A | −0.1457 | −0.0640 | 0.1832 | 0.115* | |
H26B | −0.0750 | −0.0062 | 0.1424 | 0.115* | |
H26C | −0.1588 | 0.1662 | 0.1519 | 0.115* | |
O1 | −0.00458 (15) | 0.3976 (4) | 0.06997 (8) | 0.0436 (6) | |
O2 | 0.54118 (13) | 0.5310 (3) | 0.38362 (7) | 0.0301 (5) | |
O3 | −0.00269 (15) | 0.3819 (4) | 0.18412 (9) | 0.0468 (6) | |
O4 | 0.10805 (16) | 0.1490 (4) | 0.15843 (9) | 0.0468 (6) | |
Cl1 | 0.30566 (6) | 1.39074 (16) | −0.10447 (3) | 0.0484 (3) | |
Cl2 | 0.38884 (5) | 0.68373 (14) | 0.01551 (3) | 0.0360 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0409 (18) | 0.0292 (18) | 0.0274 (17) | −0.0051 (15) | 0.0038 (14) | 0.0047 (14) |
C2 | 0.0321 (16) | 0.0368 (19) | 0.0272 (16) | −0.0022 (15) | 0.0085 (13) | −0.0014 (15) |
C3 | 0.0288 (15) | 0.0312 (17) | 0.0210 (15) | 0.0002 (13) | 0.0014 (12) | −0.0018 (13) |
C4 | 0.0297 (15) | 0.0310 (17) | 0.0193 (15) | −0.0038 (14) | 0.0005 (12) | 0.0004 (13) |
C5 | 0.0286 (16) | 0.043 (2) | 0.0297 (17) | 0.0020 (15) | 0.0037 (13) | 0.0088 (15) |
C6 | 0.0388 (18) | 0.0384 (19) | 0.0318 (18) | 0.0057 (15) | 0.0021 (15) | 0.0072 (15) |
C7 | 0.0262 (15) | 0.0312 (17) | 0.0195 (15) | 0.0029 (13) | 0.0025 (12) | 0.0003 (13) |
C8 | 0.0254 (15) | 0.0380 (18) | 0.0198 (15) | 0.0001 (14) | −0.0003 (12) | 0.0000 (13) |
C9 | 0.0273 (15) | 0.0326 (18) | 0.0211 (15) | −0.0001 (13) | −0.0006 (12) | 0.0021 (13) |
C10 | 0.0255 (15) | 0.0407 (19) | 0.0247 (16) | −0.0023 (14) | 0.0008 (13) | 0.0023 (14) |
C11 | 0.0257 (15) | 0.0404 (19) | 0.0265 (17) | −0.0059 (15) | −0.0041 (13) | 0.0032 (15) |
C12 | 0.0301 (16) | 0.0409 (19) | 0.0215 (15) | −0.0027 (15) | −0.0026 (13) | 0.0041 (14) |
C13 | 0.0266 (15) | 0.0308 (17) | 0.0190 (15) | −0.0062 (13) | 0.0002 (12) | 0.0028 (13) |
C14 | 0.0251 (15) | 0.0311 (17) | 0.0254 (16) | 0.0000 (13) | −0.0009 (13) | 0.0041 (14) |
C15 | 0.0249 (14) | 0.0259 (16) | 0.0241 (15) | 0.0023 (13) | 0.0036 (12) | −0.0004 (13) |
C16 | 0.0198 (13) | 0.0254 (16) | 0.0157 (13) | −0.0001 (12) | 0.0020 (11) | 0.0037 (12) |
C17 | 0.0241 (14) | 0.0233 (15) | 0.0186 (14) | 0.0013 (12) | 0.0015 (11) | −0.0012 (12) |
C18 | 0.0245 (14) | 0.0294 (16) | 0.0156 (14) | −0.0020 (13) | 0.0015 (11) | 0.0011 (13) |
C19 | 0.0260 (14) | 0.0231 (16) | 0.0226 (15) | 0.0009 (13) | 0.0017 (12) | 0.0010 (13) |
C20 | 0.0285 (15) | 0.0214 (16) | 0.0218 (15) | −0.0022 (12) | 0.0051 (12) | −0.0011 (12) |
C21 | 0.0210 (14) | 0.0238 (16) | 0.0194 (14) | −0.0037 (12) | 0.0033 (11) | 0.0010 (12) |
C22 | 0.0262 (14) | 0.0252 (16) | 0.0194 (14) | −0.0062 (13) | 0.0027 (12) | −0.0005 (13) |
C23 | 0.0350 (17) | 0.0341 (18) | 0.0250 (16) | −0.0030 (14) | −0.0046 (13) | −0.0031 (14) |
C24 | 0.0263 (16) | 0.041 (2) | 0.0288 (17) | −0.0013 (15) | −0.0035 (13) | 0.0014 (16) |
C25 | 0.062 (3) | 0.081 (3) | 0.058 (3) | −0.017 (2) | 0.029 (2) | 0.015 (2) |
C26 | 0.055 (3) | 0.074 (3) | 0.104 (4) | −0.025 (2) | 0.019 (3) | −0.006 (3) |
O1 | 0.0360 (12) | 0.0607 (16) | 0.0325 (13) | −0.0196 (12) | −0.0070 (10) | 0.0123 (12) |
O2 | 0.0363 (12) | 0.0296 (12) | 0.0221 (11) | 0.0050 (9) | −0.0103 (9) | −0.0021 (9) |
O3 | 0.0386 (13) | 0.0583 (16) | 0.0455 (14) | −0.0024 (12) | 0.0160 (11) | −0.0035 (13) |
O4 | 0.0385 (13) | 0.0447 (16) | 0.0560 (16) | 0.0066 (12) | −0.0034 (12) | 0.0070 (13) |
Cl1 | 0.0578 (6) | 0.0480 (6) | 0.0407 (5) | −0.0047 (4) | 0.0109 (4) | 0.0188 (4) |
Cl2 | 0.0380 (4) | 0.0395 (5) | 0.0312 (4) | 0.0087 (4) | 0.0071 (3) | 0.0055 (4) |
Geometric parameters (Å, º) top C1—C2 | 1.378 (4) | C14—H14 | 0.9500 |
C1—C6 | 1.380 (4) | C15—C16 | 1.414 (4) |
C1—Cl1 | 1.737 (3) | C15—H15 | 0.9500 |
C2—C3 | 1.384 (4) | C16—C17 | 1.417 (4) |
C2—H2 | 0.9500 | C16—C21 | 1.423 (4) |
C3—C4 | 1.399 (4) | C17—C18 | 1.362 (4) |
C3—Cl2 | 1.745 (3) | C17—H17 | 0.9500 |
C4—C5 | 1.400 (4) | C18—O2 | 1.379 (3) |
C4—C7 | 1.479 (4) | C18—C19 | 1.412 (4) |
C5—C6 | 1.387 (4) | C19—C20 | 1.362 (4) |
C5—H5 | 0.9500 | C19—H19 | 0.9500 |
C6—H6 | 0.9500 | C20—C21 | 1.418 (4) |
C7—C12 | 1.338 (4) | C20—H20 | 0.9500 |
C7—C8 | 1.506 (4) | C21—C22 | 1.423 (4) |
C8—C9 | 1.537 (4) | C22—H22 | 0.9500 |
C8—H8A | 0.9900 | C23—O2 | 1.425 (3) |
C8—H8B | 0.9900 | C23—H23A | 0.9800 |
C9—C13 | 1.527 (4) | C23—H23B | 0.9800 |
C9—C10 | 1.529 (4) | C23—H23C | 0.9800 |
C9—H9 | 1.0000 | C24—O4 | 1.198 (4) |
C10—C24 | 1.501 (4) | C24—O3 | 1.328 (4) |
C10—C11 | 1.528 (4) | C25—O3 | 1.480 (4) |
C10—H10 | 1.0000 | C25—C26 | 1.517 (6) |
C11—O1 | 1.220 (3) | C25—H25A | 0.9900 |
C11—C12 | 1.459 (4) | C25—H25B | 0.9900 |
C12—H12 | 0.9500 | C26—H26A | 0.9800 |
C13—C22 | 1.368 (4) | C26—H26B | 0.9800 |
C13—C14 | 1.417 (4) | C26—H26C | 0.9800 |
C14—C15 | 1.374 (4) | | |
| | | |
C2—C1—C6 | 121.4 (3) | C15—C14—H14 | 119.4 |
C2—C1—Cl1 | 119.6 (2) | C13—C14—H14 | 119.4 |
C6—C1—Cl1 | 119.0 (2) | C14—C15—C16 | 121.0 (3) |
C1—C2—C3 | 118.9 (3) | C14—C15—H15 | 119.5 |
C1—C2—H2 | 120.5 | C16—C15—H15 | 119.5 |
C3—C2—H2 | 120.5 | C15—C16—C17 | 122.3 (3) |
C2—C3—C4 | 122.4 (3) | C15—C16—C21 | 118.2 (2) |
C2—C3—Cl2 | 117.1 (2) | C17—C16—C21 | 119.5 (2) |
C4—C3—Cl2 | 120.5 (2) | C18—C17—C16 | 120.0 (3) |
C3—C4—C5 | 116.2 (3) | C18—C17—H17 | 120.0 |
C3—C4—C7 | 125.2 (3) | C16—C17—H17 | 120.0 |
C5—C4—C7 | 118.6 (3) | C17—C18—O2 | 125.3 (3) |
C6—C5—C4 | 122.7 (3) | C17—C18—C19 | 120.9 (2) |
C6—C5—H5 | 118.7 | O2—C18—C19 | 113.8 (2) |
C4—C5—H5 | 118.7 | C20—C19—C18 | 120.1 (3) |
C1—C6—C5 | 118.4 (3) | C20—C19—H19 | 119.9 |
C1—C6—H6 | 120.8 | C18—C19—H19 | 119.9 |
C5—C6—H6 | 120.8 | C19—C20—C21 | 120.9 (3) |
C12—C7—C4 | 118.7 (3) | C19—C20—H20 | 119.5 |
C12—C7—C8 | 121.6 (3) | C21—C20—H20 | 119.5 |
C4—C7—C8 | 119.3 (2) | C20—C21—C16 | 118.5 (2) |
C7—C8—C9 | 113.1 (2) | C20—C21—C22 | 122.3 (3) |
C7—C8—H8A | 109.0 | C16—C21—C22 | 119.2 (2) |
C9—C8—H8A | 109.0 | C13—C22—C21 | 121.6 (3) |
C7—C8—H8B | 109.0 | C13—C22—H22 | 119.2 |
C9—C8—H8B | 109.0 | C21—C22—H22 | 119.2 |
H8A—C8—H8B | 107.8 | O2—C23—H23A | 109.5 |
C13—C9—C10 | 112.9 (2) | O2—C23—H23B | 109.5 |
C13—C9—C8 | 110.5 (2) | H23A—C23—H23B | 109.5 |
C10—C9—C8 | 110.4 (2) | O2—C23—H23C | 109.5 |
C13—C9—H9 | 107.6 | H23A—C23—H23C | 109.5 |
C10—C9—H9 | 107.6 | H23B—C23—H23C | 109.5 |
C8—C9—H9 | 107.6 | O4—C24—O3 | 125.1 (3) |
C24—C10—C11 | 106.7 (2) | O4—C24—C10 | 123.0 (3) |
C24—C10—C9 | 114.1 (2) | O3—C24—C10 | 111.9 (3) |
C11—C10—C9 | 110.3 (2) | O3—C25—C26 | 111.3 (3) |
C24—C10—H10 | 108.6 | O3—C25—H25A | 109.4 |
C11—C10—H10 | 108.6 | C26—C25—H25A | 109.4 |
C9—C10—H10 | 108.6 | O3—C25—H25B | 109.4 |
O1—C11—C12 | 122.2 (3) | C26—C25—H25B | 109.4 |
O1—C11—C10 | 120.8 (3) | H25A—C25—H25B | 108.0 |
C12—C11—C10 | 116.9 (2) | C25—C26—H26A | 109.5 |
C7—C12—C11 | 123.0 (3) | C25—C26—H26B | 109.5 |
C7—C12—H12 | 118.5 | H26A—C26—H26B | 109.5 |
C11—C12—H12 | 118.5 | C25—C26—H26C | 109.5 |
C22—C13—C14 | 118.7 (3) | H26A—C26—H26C | 109.5 |
C22—C13—C9 | 121.4 (3) | H26B—C26—H26C | 109.5 |
C14—C13—C9 | 119.8 (3) | C18—O2—C23 | 117.1 (2) |
C15—C14—C13 | 121.1 (3) | C24—O3—C25 | 114.9 (3) |
| | | |
C6—C1—C2—C3 | 0.8 (5) | C8—C9—C13—C22 | −120.9 (3) |
Cl1—C1—C2—C3 | −179.4 (2) | C10—C9—C13—C14 | −67.7 (3) |
C1—C2—C3—C4 | −0.3 (4) | C8—C9—C13—C14 | 56.4 (3) |
C1—C2—C3—Cl2 | 177.1 (2) | C22—C13—C14—C15 | 2.5 (4) |
C2—C3—C4—C5 | 0.0 (4) | C9—C13—C14—C15 | −174.9 (3) |
Cl2—C3—C4—C5 | −177.3 (2) | C13—C14—C15—C16 | 1.6 (4) |
C2—C3—C4—C7 | 178.0 (3) | C14—C15—C16—C17 | 173.6 (3) |
Cl2—C3—C4—C7 | 0.7 (4) | C14—C15—C16—C21 | −4.4 (4) |
C3—C4—C5—C6 | −0.1 (5) | C15—C16—C17—C18 | −178.1 (3) |
C7—C4—C5—C6 | −178.3 (3) | C21—C16—C17—C18 | 0.0 (4) |
C2—C1—C6—C5 | −1.0 (5) | C16—C17—C18—O2 | 177.6 (2) |
Cl1—C1—C6—C5 | 179.2 (2) | C16—C17—C18—C19 | −1.3 (4) |
C4—C5—C6—C1 | 0.6 (5) | C17—C18—C19—C20 | 1.1 (4) |
C3—C4—C7—C12 | −122.5 (3) | O2—C18—C19—C20 | −177.9 (2) |
C5—C4—C7—C12 | 55.4 (4) | C18—C19—C20—C21 | 0.4 (4) |
C3—C4—C7—C8 | 63.4 (4) | C19—C20—C21—C16 | −1.7 (4) |
C5—C4—C7—C8 | −118.6 (3) | C19—C20—C21—C22 | 174.4 (3) |
C12—C7—C8—C9 | 20.0 (4) | C15—C16—C21—C20 | 179.6 (2) |
C4—C7—C8—C9 | −166.2 (3) | C17—C16—C21—C20 | 1.4 (4) |
C7—C8—C9—C13 | −173.5 (2) | C15—C16—C21—C22 | 3.4 (4) |
C7—C8—C9—C10 | −47.9 (3) | C17—C16—C21—C22 | −174.8 (2) |
C13—C9—C10—C24 | −59.8 (3) | C14—C13—C22—C21 | −3.5 (4) |
C8—C9—C10—C24 | 176.0 (3) | C9—C13—C22—C21 | 173.9 (2) |
C13—C9—C10—C11 | −179.8 (3) | C20—C21—C22—C13 | −175.5 (3) |
C8—C9—C10—C11 | 56.0 (3) | C16—C21—C22—C13 | 0.6 (4) |
C24—C10—C11—O1 | 19.1 (4) | C11—C10—C24—O4 | 81.0 (4) |
C9—C10—C11—O1 | 143.5 (3) | C9—C10—C24—O4 | −41.0 (4) |
C24—C10—C11—C12 | −161.8 (3) | C11—C10—C24—O3 | −96.8 (3) |
C9—C10—C11—C12 | −37.4 (4) | C9—C10—C24—O3 | 141.2 (3) |
C4—C7—C12—C11 | −173.8 (3) | C17—C18—O2—C23 | −10.7 (4) |
C8—C7—C12—C11 | 0.1 (5) | C19—C18—O2—C23 | 168.3 (2) |
O1—C11—C12—C7 | −171.8 (3) | O4—C24—O3—C25 | −5.8 (5) |
C10—C11—C12—C7 | 9.1 (5) | C10—C24—O3—C25 | 172.0 (3) |
C10—C9—C13—C22 | 114.9 (3) | C26—C25—O3—C24 | −81.2 (4) |
Hydrogen-bond geometry (Å, º) top D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O1i | 0.95 | 2.49 | 3.411 (4) | 164 |
C8—H8A···O4ii | 0.99 | 2.52 | 3.388 (4) | 146 |
C8—H8B···Cl2 | 0.99 | 2.69 | 3.365 (3) | 125 |
C12—H12···O1iii | 0.95 | 2.42 | 3.354 (4) | 168 |
C14—H14···O4ii | 0.95 | 2.33 | 3.270 (4) | 170 |
C17—H17···Cl1iv | 0.95 | 2.76 | 3.635 (3) | 153 |
Symmetry codes: (i) −x, −y+2, −z; (ii) x, y+1, z; (iii) −x, −y+1, −z; (iv) x, −y+5/2, z+1/2. |
Experimental details
Crystal data |
Chemical formula | C26H22Cl2O4 |
Mr | 469.34 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 120 |
a, b, c (Å) | 14.2156 (4), 5.8647 (2), 27.3752 (9) |
β (°) | 94.840 (2) |
V (Å3) | 2274.14 (13) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.32 |
Crystal size (mm) | 0.20 × 0.10 × 0.07 |
|
Data collection |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 24499, 5209, 3171 |
Rint | 0.081 |
(sin θ/λ)max (Å−1) | 0.650 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.062, 0.160, 1.05 |
No. of reflections | 5209 |
No. of parameters | 291 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.39, −0.32 |
Hydrogen-bond geometry (Å, º) top D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O1i | 0.95 | 2.49 | 3.411 (4) | 164 |
C8—H8A···O4ii | 0.99 | 2.52 | 3.388 (4) | 146 |
C8—H8B···Cl2 | 0.99 | 2.69 | 3.365 (3) | 125 |
C12—H12···O1iii | 0.95 | 2.42 | 3.354 (4) | 168 |
C14—H14···O4ii | 0.95 | 2.33 | 3.270 (4) | 170 |
C17—H17···Cl1iv | 0.95 | 2.76 | 3.635 (3) | 153 |
Symmetry codes: (i) −x, −y+2, −z; (ii) x, y+1, z; (iii) −x, −y+1, −z; (iv) x, −y+5/2, z+1/2. |
Acknowledgements
ANM thanks the University of Mysore for research facilities. HSY thanks the University of Mysore for sanctioning sabbatical leave.
References
Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Li, H., Mayekar, A. N., Narayana, B., Yathirajan, H. S. & Harrison, W. T. A. (2009a). Acta Cryst. E65, o1186. Web of Science CSD CrossRef IUCr Journals Google Scholar
Li, H., Mayekar, A. N., Narayana, B., Yathirajan, H. S. & Harrison, W. T. A. (2009b). Acta Cryst. E65, o1533. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
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The structure of the title compound, (I), (Fig. 1), was determined as part of our ongoing structural studies (Li et al., 2009a,b) of substituted cyclohexenones.
The cyclohexenone ring (C7–C12) in (I) adopts an approximate half-chair conformation with C7/C8/C11/C12 statistically coplanar [r.m.s. deviation = 0.0004 Å; individual deviations = 0.0006 (19), -0.0003 (9), 0.0003 (9) and -0.006 (2) Å, respectively] and C9 and C10 displaced from their mean plane by -0.485 (6) and 0.218 (6) Å, respectively. Unlike the equivalent atoms in the related structures ethyl 6-(6-methoxy-2-naphthyl)-4-(4-methylphenyl)-2-oxocyclohex-3- ene-1-carboxylate, (II), (Li et al., 2009a) and ethyl 6-(6-methoxy-2-naphthyl)-2-oxo-4-(2-thienyl)cyclohex-3- ene-1-carboxylate, (III), (Li et al., 2009b), C9 and C10 in (I) do not display positional disorder. Both atoms are stereogenic centres: in the arbitrarily chosen asymmetric molecule, C9 has R configuration and C10 has S, but crystal symmetry generates a racemic mixture of enantiomers.
The dihedral angles between C7/C8/C11/C12 and the benzene (C1–C6) and naphthalene (C13–C22) ring systems are 59.26 (13) and 79.94 (9)°, respectively. The dihedral angle between the aromatic rings systems in (I) is 77.14 (7)°: equivalent values in (II) and (III) are 73.10 (5) and 86.04 (16)°, respectively. The naphthalene ring system (atoms C13–C22) in (I) shows rather high deviations from planarity: the r.m.s. deviation is 0.044Å and maximum deviations are 0.074 (2)Å for C13 and -0.055 (2) for C21. If the two benzene rings (C13/C14/C15/C16/C21/C22 and C16–C21) are considered separately, their r.m.s. deviations are 0.018 and 0.007 Å, respectively, and the dihedral angle between them is 4.85 (16)°. Atom C23 of the terminal methyl group is displaced from the naphthalene ring by 0.466 (4) Å. A short intramolecular C8—H8B···Cl2 contact (Table 1) generates an S(6) ring.
In the crystal, the molecules are linked by C—H···O and C—H···Cl interactions to generate a three-dimensional network.