2-[1-(3,4-Dichloro­phen­yl)-3-oxo-3-phenyl­prop­yl]-3,4-dihydro-2H-naphthalen-1-one

Rong, L.-C.; Li, X.-Y.; Yao, C.-S.; Wang, H.-Y.; Shi, D.-Q.

doi:10.1107/S1600536805039449

2-[1-(3,4-Dichlorophenyl)-3-oxo-3-phenylpropyl]-3,4-dihydro-2H-naphthalen-1-one

L.-C. Rong, X.-Y. Li, C.-S. Yao, H.-Y. Wang and D.-Q. Shi

The title compound, C₂₅H₂₀Cl₂O₂, was synthesized by the reaction of 3,4-dihydronaphthalen-1(2H)-one with 3-(3,4-dichlorophenyl)-1-phenylprop-2-en-1-one under solvent-free conditions at room temperature. X-ray analysis reveals that the cyclohexanone ring adopts an envelope conformation

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805039449/ci6714sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805039449/ci6714Isup2.hkl Contains datablock I

CCDC reference: 296537

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.005 Å
R factor = 0.053
wR factor = 0.148
Data-to-parameter ratio = 10.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C12
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C13
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9     ..  CG1     ..       2.97 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 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

Comment top

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).

Experimental top

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.

Computing details top

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.

Figures top

Fig. 1. The structure of (I), showing 30% probability displacement ellipsoids.

2-[1-(3,4-Dichlorophenyl)-3-oxo-3-phenylpropyl]-3,4-dihydro-2H- naphthalen-1-one top

Crystal data top

C₂₅H₂₀Cl₂O₂	F(000) = 880
M_r = 423.31	D_x = 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

Data collection top

Bruker SMART CCD area-detector diffractometer	3669 independent reflections
Radiation source: fine-focus sealed tube	2008 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.874, T_max = 0.910	k = −16→21
10745 measured reflections	l = −13→13

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.148	All H-atom parameters refined
S = 1.00	w = 1/[σ²(F_o²) + (0.074P)²] where P = (F_o² + 2F_c²)/3
3669 reflections	(Δ/σ)_max = 0.001
342 parameters	Δρ_max = 0.46 e Å⁻³
4 restraints	Δρ_min = −0.58 e Å⁻³

Crystal data top

C₂₅H₂₀Cl₂O₂	V = 2085.4 (6) Å³
M_r = 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)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3669 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2008 reflections with I > 2σ(I)
T_min = 0.874, T_max = 0.910	R_int = 0.038
10745 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	4 restraints
wR(F²) = 0.148	All H-atom parameters refined
S = 1.00	Δρ_max = 0.46 e Å⁻³
3669 reflections	Δρ_min = −0.58 e Å⁻³
342 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	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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
M_r	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)
T_min, T_max	0.874, 0.910
No. of measured, independent and observed [I > 2σ(I)] reflections	10745, 3669, 2008
R_int	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
Δρ_max, Δρ_min (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.

Selected geometric parameters (Å, º) top

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)