Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805039449/ci6714sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805039449/ci6714Isup2.hkl |
CCDC reference: 296537
Compound (I) was prepared by the reaction of 3,4-dihydronaphthalen-1(2H)-one (2 mmol) with 3-(3,4-dichlorophenyl)-1-phenylprop-2-en-1-one (2 mmol) catalysed by NaOH (0.2 g) under solvent-free condition (m.p. 469–470 K). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution.
H atoms were located in a difference map and refined isotropically. The C—H distances range from 0.89 (3) to 1.04 (3) Å.
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.
C25H20Cl2O2 | F(000) = 880 |
Mr = 423.31 | Dx = 1.348 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 2344 reflections |
a = 9.9826 (19) Å | θ = 2.3–21.1° |
b = 17.858 (3) Å | µ = 0.33 mm−1 |
c = 11.703 (2) Å | T = 298 K |
β = 91.667 (3)° | Block, colourless |
V = 2085.4 (6) Å3 | 0.42 × 0.37 × 0.29 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 3669 independent reflections |
Radiation source: fine-focus sealed tube | 2008 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
ϕ and ω scans | θmax = 25.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→11 |
Tmin = 0.874, Tmax = 0.910 | k = −16→21 |
10745 measured reflections | l = −13→13 |
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.148 | All H-atom parameters refined |
S = 1.00 | w = 1/[σ2(Fo2) + (0.074P)2] where P = (Fo2 + 2Fc2)/3 |
3669 reflections | (Δ/σ)max = 0.001 |
342 parameters | Δρmax = 0.46 e Å−3 |
4 restraints | Δρmin = −0.58 e Å−3 |
C25H20Cl2O2 | V = 2085.4 (6) Å3 |
Mr = 423.31 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.9826 (19) Å | µ = 0.33 mm−1 |
b = 17.858 (3) Å | T = 298 K |
c = 11.703 (2) Å | 0.42 × 0.37 × 0.29 mm |
β = 91.667 (3)° |
Bruker SMART CCD area-detector diffractometer | 3669 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2008 reflections with I > 2σ(I) |
Tmin = 0.874, Tmax = 0.910 | Rint = 0.038 |
10745 measured reflections |
R[F2 > 2σ(F2)] = 0.053 | 4 restraints |
wR(F2) = 0.148 | All H-atom parameters refined |
S = 1.00 | Δρmax = 0.46 e Å−3 |
3669 reflections | Δρmin = −0.58 e Å−3 |
342 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 | 0.60289 (12) | 0.94496 (7) | −0.09359 (14) | 0.1434 (6) | |
Cl2 | 0.86756 (12) | 1.00483 (5) | −0.19962 (8) | 0.0974 (4) | |
O1 | 0.8679 (2) | 0.65171 (12) | −0.07565 (18) | 0.0733 (6) | |
O2 | 0.7770 (2) | 0.65610 (12) | 0.30267 (16) | 0.0706 (6) | |
C1 | 0.8762 (3) | 0.73942 (16) | 0.1209 (2) | 0.0501 (7) | |
C2 | 0.9834 (3) | 0.68126 (18) | 0.0988 (3) | 0.0556 (8) | |
C3 | 0.9667 (3) | 0.64200 (16) | −0.0155 (2) | 0.0540 (8) | |
C4 | 1.0748 (3) | 0.58997 (15) | −0.0512 (2) | 0.0538 (7) | |
C5 | 1.1766 (4) | 0.56655 (19) | 0.0213 (3) | 0.0677 (9) | |
C6 | 1.2723 (4) | 0.5164 (2) | −0.0160 (4) | 0.0824 (11) | |
C7 | 1.2677 (5) | 0.4908 (2) | −0.1250 (4) | 0.0853 (11) | |
C8 | 1.1680 (5) | 0.5146 (2) | −0.1987 (4) | 0.0886 (12) | |
C9 | 1.0726 (4) | 0.5633 (2) | −0.1621 (3) | 0.0769 (10) | |
C10 | 0.8753 (3) | 0.80494 (16) | 0.0377 (2) | 0.0519 (7) | |
C11 | 0.7566 (4) | 0.84144 (18) | 0.0114 (3) | 0.0626 (9) | |
C12 | 0.7534 (3) | 0.90283 (18) | −0.0610 (3) | 0.0688 (9) | |
C13 | 0.8703 (4) | 0.92844 (16) | −0.1086 (2) | 0.0619 (8) | |
C14 | 0.9871 (4) | 0.89229 (19) | −0.0846 (3) | 0.0701 (9) | |
C15 | 0.9897 (4) | 0.8315 (2) | −0.0130 (3) | 0.0664 (9) | |
C16 | 0.8851 (3) | 0.76833 (17) | 0.2450 (2) | 0.0514 (7) | |
C17 | 0.8430 (3) | 0.71060 (16) | 0.3308 (2) | 0.0515 (7) | |
C18 | 0.8804 (3) | 0.72456 (16) | 0.4529 (2) | 0.0510 (7) | |
C19 | 0.8354 (3) | 0.67466 (19) | 0.5357 (3) | 0.0606 (8) | |
C20 | 0.8583 (4) | 0.6883 (2) | 0.6488 (3) | 0.0741 (10) | |
C21 | 0.9271 (4) | 0.7509 (3) | 0.6826 (3) | 0.0827 (11) | |
C22 | 0.9760 (4) | 0.7997 (2) | 0.6031 (3) | 0.0754 (10) | |
C23 | 0.9549 (3) | 0.78684 (16) | 0.4863 (2) | 0.0572 (8) | |
C24 | 1.0121 (5) | 0.8382 (2) | 0.3985 (3) | 0.0688 (10) | |
C25 | 1.0214 (3) | 0.8009 (2) | 0.2830 (3) | 0.0624 (9) | |
H1 | 0.790 (3) | 0.7166 (13) | 0.114 (2) | 0.047 (8)* | |
H2 | 0.980 (2) | 0.6412 (16) | 0.156 (2) | 0.057 (8)* | |
H3 | 1.074 (3) | 0.7036 (15) | 0.101 (2) | 0.056 (8)* | |
H4 | 1.185 (3) | 0.5857 (16) | 0.094 (2) | 0.066 (9)* | |
H5 | 1.341 (4) | 0.5037 (18) | 0.041 (3) | 0.087 (12)* | |
H6 | 1.338 (3) | 0.4534 (18) | −0.156 (3) | 0.084 (10)* | |
H7 | 1.168 (4) | 0.501 (2) | −0.2777 (18) | 0.116 (14)* | |
H8 | 1.001 (3) | 0.5799 (17) | −0.208 (3) | 0.076 (11)* | |
H9 | 0.679 (3) | 0.8232 (16) | 0.040 (2) | 0.063 (9)* | |
H10 | 1.0628 (16) | 0.9183 (13) | −0.115 (2) | 0.087 (11)* | |
H11 | 1.070 (4) | 0.8055 (18) | 0.009 (3) | 0.086 (11)* | |
H12 | 0.821 (3) | 0.8110 (16) | 0.250 (2) | 0.063 (8)* | |
H13 | 0.792 (3) | 0.6279 (15) | 0.508 (2) | 0.054 (8)* | |
H14 | 0.826 (3) | 0.6590 (17) | 0.702 (3) | 0.070 (10)* | |
H15 | 0.943 (3) | 0.7639 (17) | 0.760 (3) | 0.078 (10)* | |
H16 | 1.021 (3) | 0.8432 (18) | 0.619 (3) | 0.069 (10)* | |
H17 | 0.949 (3) | 0.8800 (17) | 0.386 (2) | 0.066 (9)* | |
H18 | 1.095 (3) | 0.8524 (17) | 0.423 (3) | 0.073 (11)* | |
H19 | 1.053 (3) | 0.8372 (16) | 0.223 (2) | 0.068 (9)* | |
H20 | 1.094 (3) | 0.7599 (18) | 0.286 (2) | 0.073 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0794 (8) | 0.1264 (10) | 0.2243 (15) | 0.0274 (7) | 0.0026 (8) | 0.0879 (10) |
Cl2 | 0.1310 (9) | 0.0719 (7) | 0.0890 (7) | −0.0047 (5) | 0.0013 (6) | 0.0306 (5) |
O1 | 0.0724 (16) | 0.0862 (17) | 0.0606 (13) | 0.0086 (12) | −0.0080 (12) | −0.0068 (11) |
O2 | 0.0828 (16) | 0.0711 (15) | 0.0580 (13) | −0.0271 (12) | 0.0041 (11) | −0.0014 (11) |
C1 | 0.0515 (19) | 0.0530 (18) | 0.0458 (17) | −0.0029 (15) | 0.0026 (14) | 0.0016 (14) |
C2 | 0.062 (2) | 0.0536 (19) | 0.0511 (19) | 0.0044 (17) | 0.0023 (15) | 0.0035 (15) |
C3 | 0.062 (2) | 0.0528 (19) | 0.0475 (17) | −0.0046 (15) | 0.0055 (15) | 0.0039 (14) |
C4 | 0.064 (2) | 0.0448 (17) | 0.0533 (18) | −0.0053 (15) | 0.0080 (15) | −0.0005 (14) |
C5 | 0.080 (3) | 0.064 (2) | 0.060 (2) | 0.0104 (18) | 0.0053 (19) | −0.0061 (18) |
C6 | 0.085 (3) | 0.074 (3) | 0.088 (3) | 0.012 (2) | −0.004 (2) | −0.005 (2) |
C7 | 0.098 (3) | 0.067 (3) | 0.092 (3) | 0.011 (2) | 0.018 (3) | −0.018 (2) |
C8 | 0.110 (3) | 0.083 (3) | 0.073 (3) | 0.015 (2) | 0.006 (3) | −0.020 (2) |
C9 | 0.090 (3) | 0.074 (2) | 0.067 (2) | 0.015 (2) | −0.004 (2) | −0.0158 (19) |
C10 | 0.0566 (19) | 0.0519 (18) | 0.0473 (16) | 0.0025 (15) | 0.0024 (14) | −0.0025 (14) |
C11 | 0.055 (2) | 0.061 (2) | 0.072 (2) | −0.0003 (17) | 0.0054 (17) | 0.0091 (17) |
C12 | 0.062 (2) | 0.064 (2) | 0.079 (2) | 0.0089 (17) | −0.0076 (17) | 0.0109 (18) |
C13 | 0.078 (2) | 0.0519 (19) | 0.0559 (18) | −0.0087 (17) | 0.0018 (17) | 0.0037 (14) |
C14 | 0.070 (2) | 0.072 (2) | 0.069 (2) | −0.0076 (19) | 0.0094 (18) | 0.0129 (18) |
C15 | 0.057 (2) | 0.075 (2) | 0.068 (2) | 0.0037 (18) | 0.0056 (17) | 0.0174 (18) |
C16 | 0.0541 (19) | 0.0488 (18) | 0.0517 (17) | 0.0012 (15) | 0.0049 (14) | 0.0019 (14) |
C17 | 0.0498 (18) | 0.0544 (19) | 0.0505 (18) | 0.0009 (14) | 0.0054 (14) | −0.0016 (14) |
C18 | 0.0486 (17) | 0.0545 (18) | 0.0500 (17) | 0.0023 (14) | 0.0044 (13) | 0.0021 (14) |
C19 | 0.057 (2) | 0.069 (2) | 0.056 (2) | 0.0013 (17) | 0.0027 (15) | 0.0053 (17) |
C20 | 0.076 (2) | 0.090 (3) | 0.057 (2) | −0.004 (2) | −0.0010 (19) | 0.012 (2) |
C21 | 0.099 (3) | 0.104 (3) | 0.045 (2) | 0.006 (2) | 0.001 (2) | −0.002 (2) |
C22 | 0.090 (3) | 0.072 (3) | 0.064 (2) | −0.007 (2) | −0.0035 (19) | −0.015 (2) |
C23 | 0.063 (2) | 0.059 (2) | 0.0498 (18) | 0.0054 (15) | 0.0052 (15) | −0.0025 (15) |
C24 | 0.083 (3) | 0.057 (2) | 0.066 (2) | −0.014 (2) | 0.004 (2) | −0.0092 (18) |
C25 | 0.071 (2) | 0.059 (2) | 0.057 (2) | −0.0137 (19) | 0.0077 (17) | −0.0016 (17) |
Cl1—C12 | 1.714 (3) | C11—H9 | 0.91 (3) |
Cl2—C13 | 1.730 (3) | C12—C13 | 1.386 (4) |
O1—C3 | 1.207 (3) | C13—C14 | 1.355 (4) |
O2—C17 | 1.215 (3) | C14—C15 | 1.371 (4) |
C1—C2 | 1.518 (4) | C14—H10 | 0.966 (13) |
C1—C10 | 1.522 (4) | C15—H11 | 0.96 (3) |
C1—C16 | 1.541 (4) | C16—C17 | 1.508 (4) |
C1—H1 | 0.95 (3) | C16—C25 | 1.534 (4) |
C2—C3 | 1.515 (4) | C16—H12 | 1.00 (3) |
C2—H2 | 0.98 (3) | C17—C18 | 1.487 (4) |
C2—H3 | 0.99 (3) | C18—C23 | 1.387 (4) |
C3—C4 | 1.492 (4) | C18—C19 | 1.401 (4) |
C4—C5 | 1.370 (4) | C19—C20 | 1.358 (4) |
C4—C9 | 1.382 (4) | C19—H13 | 0.99 (3) |
C5—C6 | 1.389 (5) | C20—C21 | 1.365 (5) |
C5—H4 | 0.91 (3) | C20—H14 | 0.89 (3) |
C6—C7 | 1.355 (5) | C21—C22 | 1.374 (5) |
C6—H5 | 0.97 (4) | C21—H15 | 0.94 (3) |
C7—C8 | 1.365 (6) | C22—C23 | 1.396 (4) |
C7—H6 | 1.04 (3) | C22—H16 | 0.91 (3) |
C8—C9 | 1.368 (5) | C23—C24 | 1.502 (4) |
C8—H7 | 0.956 (19) | C24—C25 | 1.512 (4) |
C9—H8 | 0.93 (3) | C24—H17 | 0.98 (3) |
C10—C11 | 1.379 (4) | C24—H18 | 0.91 (3) |
C10—C15 | 1.386 (4) | C25—H19 | 1.02 (3) |
C11—C12 | 1.385 (4) | C25—H20 | 1.03 (3) |
C2—C1—C10 | 114.1 (2) | C13—C14—C15 | 120.4 (3) |
C2—C1—C16 | 111.6 (2) | C13—C14—H10 | 111.8 (13) |
C10—C1—C16 | 110.1 (2) | C15—C14—H10 | 127.4 (13) |
C2—C1—H1 | 109.3 (15) | C14—C15—C10 | 122.0 (3) |
C10—C1—H1 | 106.8 (15) | C14—C15—H11 | 123 (2) |
C16—C1—H1 | 104.4 (15) | C10—C15—H11 | 115 (2) |
C3—C2—C1 | 114.0 (3) | C17—C16—C25 | 109.2 (2) |
C3—C2—H2 | 105.0 (15) | C17—C16—C1 | 112.9 (2) |
C1—C2—H2 | 110.1 (15) | C25—C16—C1 | 115.3 (2) |
C3—C2—H3 | 106.9 (15) | C17—C16—H12 | 107.0 (16) |
C1—C2—H3 | 111.6 (15) | C25—C16—H12 | 105.2 (16) |
H2—C2—H3 | 109 (2) | C1—C16—H12 | 106.7 (16) |
O1—C3—C4 | 120.8 (3) | O2—C17—C18 | 120.9 (3) |
O1—C3—C2 | 121.0 (3) | O2—C17—C16 | 121.8 (3) |
C4—C3—C2 | 118.3 (3) | C18—C17—C16 | 117.3 (2) |
C5—C4—C9 | 117.9 (3) | C23—C18—C19 | 119.7 (3) |
C5—C4—C3 | 123.1 (3) | C23—C18—C17 | 121.5 (3) |
C9—C4—C3 | 119.0 (3) | C19—C18—C17 | 118.8 (3) |
C4—C5—C6 | 120.5 (4) | C20—C19—C18 | 120.8 (3) |
C4—C5—H4 | 120.6 (19) | C20—C19—H13 | 122.2 (15) |
C6—C5—H4 | 118.9 (19) | C18—C19—H13 | 116.8 (15) |
C7—C6—C5 | 120.5 (4) | C19—C20—C21 | 119.9 (4) |
C7—C6—H5 | 125 (2) | C19—C20—H14 | 122 (2) |
C5—C6—H5 | 115 (2) | C21—C20—H14 | 118 (2) |
C6—C7—C8 | 119.6 (4) | C20—C21—C22 | 120.6 (4) |
C6—C7—H6 | 122.7 (18) | C20—C21—H15 | 123.2 (19) |
C8—C7—H6 | 117.7 (18) | C22—C21—H15 | 116.2 (19) |
C7—C8—C9 | 120.1 (4) | C21—C22—C23 | 120.9 (4) |
C7—C8—H7 | 121 (2) | C21—C22—H16 | 125.7 (19) |
C9—C8—H7 | 119 (2) | C23—C22—H16 | 113 (2) |
C8—C9—C4 | 121.4 (4) | C18—C23—C22 | 118.1 (3) |
C8—C9—H8 | 123 (2) | C18—C23—C24 | 120.5 (3) |
C4—C9—H8 | 115 (2) | C22—C23—C24 | 121.3 (3) |
C11—C10—C15 | 117.2 (3) | C23—C24—C25 | 112.2 (3) |
C11—C10—C1 | 119.7 (3) | C23—C24—H17 | 108.2 (17) |
C15—C10—C1 | 123.2 (3) | C25—C24—H17 | 104.8 (17) |
C10—C11—C12 | 121.0 (3) | C23—C24—H18 | 109 (2) |
C10—C11—H9 | 118.8 (19) | C25—C24—H18 | 109 (2) |
C12—C11—H9 | 120.2 (19) | H17—C24—H18 | 114 (3) |
C11—C12—C13 | 120.2 (3) | C24—C25—C16 | 110.4 (3) |
C11—C12—Cl1 | 119.2 (3) | C24—C25—H19 | 111.7 (16) |
C13—C12—Cl1 | 120.6 (3) | C16—C25—H19 | 109.2 (16) |
C14—C13—C12 | 119.3 (3) | C24—C25—H20 | 110.1 (17) |
C14—C13—Cl2 | 120.1 (3) | C16—C25—H20 | 111.0 (17) |
C12—C13—Cl2 | 120.6 (3) | H19—C25—H20 | 104 (2) |
C10—C1—C2—C3 | −63.4 (4) | C11—C10—C15—C14 | 1.3 (5) |
C16—C1—C2—C3 | 171.0 (3) | C1—C10—C15—C14 | −177.6 (3) |
C1—C2—C3—O1 | −7.6 (4) | C2—C1—C16—C17 | −70.5 (3) |
C1—C2—C3—C4 | 173.4 (3) | C10—C1—C16—C17 | 161.8 (2) |
O1—C3—C4—C5 | −168.0 (3) | C2—C1—C16—C25 | 55.9 (4) |
C2—C3—C4—C5 | 11.1 (4) | C10—C1—C16—C25 | −71.9 (3) |
O1—C3—C4—C9 | 11.5 (4) | C25—C16—C17—O2 | −147.7 (3) |
C2—C3—C4—C9 | −169.4 (3) | C1—C16—C17—O2 | −18.1 (4) |
C9—C4—C5—C6 | −1.3 (5) | C25—C16—C17—C18 | 34.9 (3) |
C3—C4—C5—C6 | 178.2 (3) | C1—C16—C17—C18 | 164.5 (2) |
C4—C5—C6—C7 | 1.0 (6) | O2—C17—C18—C23 | −179.5 (3) |
C5—C6—C7—C8 | 0.0 (6) | C16—C17—C18—C23 | −2.1 (4) |
C6—C7—C8—C9 | −0.7 (6) | O2—C17—C18—C19 | −1.6 (4) |
C7—C8—C9—C4 | 0.4 (6) | C16—C17—C18—C19 | 175.8 (2) |
C5—C4—C9—C8 | 0.6 (5) | C23—C18—C19—C20 | 3.1 (4) |
C3—C4—C9—C8 | −178.9 (3) | C17—C18—C19—C20 | −174.9 (3) |
C2—C1—C10—C11 | 150.2 (3) | C18—C19—C20—C21 | −0.6 (5) |
C16—C1—C10—C11 | −83.4 (3) | C19—C20—C21—C22 | −1.4 (6) |
C2—C1—C10—C15 | −30.9 (4) | C20—C21—C22—C23 | 0.9 (6) |
C16—C1—C10—C15 | 95.5 (3) | C19—C18—C23—C22 | −3.5 (4) |
C15—C10—C11—C12 | −1.2 (5) | C17—C18—C23—C22 | 174.4 (3) |
C1—C10—C11—C12 | 177.8 (3) | C19—C18—C23—C24 | 175.8 (3) |
C10—C11—C12—C13 | 0.2 (5) | C17—C18—C23—C24 | −6.3 (5) |
C10—C11—C12—Cl1 | 178.5 (3) | C21—C22—C23—C18 | 1.6 (5) |
C11—C12—C13—C14 | 0.7 (5) | C21—C22—C23—C24 | −177.7 (4) |
Cl1—C12—C13—C14 | −177.5 (3) | C18—C23—C24—C25 | −19.9 (5) |
C11—C12—C13—Cl2 | 179.7 (2) | C22—C23—C24—C25 | 159.3 (3) |
Cl1—C12—C13—Cl2 | 1.5 (4) | C23—C24—C25—C16 | 53.4 (5) |
C12—C13—C14—C15 | −0.6 (5) | C17—C16—C25—C24 | −60.5 (4) |
Cl2—C13—C14—C15 | −179.6 (3) | C1—C16—C25—C24 | 171.2 (3) |
C13—C14—C15—C10 | −0.4 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H9···Cg1i | 0.91 (3) | 2.97 (3) | 3.855 (6) | 166 (3) |
Symmetry code: (i) x−1/2, −y+3/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C25H20Cl2O2 |
Mr | 423.31 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 298 |
a, b, c (Å) | 9.9826 (19), 17.858 (3), 11.703 (2) |
β (°) | 91.667 (3) |
V (Å3) | 2085.4 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.33 |
Crystal size (mm) | 0.42 × 0.37 × 0.29 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.874, 0.910 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10745, 3669, 2008 |
Rint | 0.038 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.053, 0.148, 1.00 |
No. of reflections | 3669 |
No. of parameters | 342 |
No. of restraints | 4 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.46, −0.58 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999), SHELXTL.
Cl1—C12 | 1.714 (3) | O1—C3 | 1.207 (3) |
Cl2—C13 | 1.730 (3) | O2—C17 | 1.215 (3) |
C10—C1—C16 | 110.1 (2) | C11—C10—C15 | 117.2 (3) |
C3—C2—C1 | 114.0 (3) | C15—C10—C1 | 123.2 (3) |
C5—C4—C9 | 117.9 (3) | C17—C16—C1 | 112.9 (2) |
C5—C4—C3 | 123.1 (3) | C25—C16—C1 | 115.3 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C11—H9···Cg1i | 0.91 (3) | 2.97 (3) | 3.855 (6) | 166 (3) |
Symmetry code: (i) x−1/2, −y+3/2, z−1/2. |
1,5-Diketones are extremely important synthetic intermediates and are desirable starting materials for preparing many heterocyclic (Arigan or Ariyan & Suschitiky, 1961) and polyfunctional compounds (Edwin & Alexanden, 1992; Gill et al., 1952). The solvent-free reaction has attracted much attention in recent years (Tanaka & Toda, 2000) and has been proved to have many advantages: reduced pollution, low costs, and simplicity in process and handling. The solid-state Michael addition has been performed well recently (Goud et al., 1995; Annunziata et al., 1997; Li et al., 1999). We report here the crystal structure of the title compound, (I), which was synthesized by the solvent-free Michael addition reaction of 3,4-dihydronaphthalen-1(2H)-one and 3-(3,4-dichlorophenyl)-1-phenylprop-2-en-1-one at room temperature.
In (I), the fused cyclohexanone ring adopts an envelope conformation (Fig.1), with the atom C25 deviating from the C16/C17/C18/C23/C24 plane by 0.684 (4) Å. The C4–C9 and C10–C15 planes form dihedral angles of 85.6 (1) and 74.6 (1)°, respectively, with respect to the C16–C24 plane. The crystal packing is stablized by C—H···π interactions involving the C18–C23 phenyl ring (centroid Cg1) (Table 2).