Ethyl 4-(2,4-dichloro-phen-yl)-6-(6-meth-oxy-2-naphth-yl)-2-oxocyclo-hex-3-ene-1-carboxyl-ate.

In the title compound, C(26)H(22)Cl(2)O(4), the cyclo-hexenone ring adopts an approximate half-chair conformation, with two C atoms displaced by -0.485 (6) and 0.218 (6) Å from the plane of the other four ring atoms. The dihedral angles between its four almost coplanar [maximum deviation = 0.006 (2) Å] atoms and the benzene and naphthalene ring systems are 59.26 (13) and 79.94 (9)°, respectively. The dihedral angle between the aromatic rings systems is 77.14 (7)°. A short intra-molecular C-H⋯Cl contact generates an S(6) ring. In the crystal, mol-ecules are linked by C-H⋯O and C-H⋯Cl inter-actions to generate a three-dimensional network.

Related literature

For related structures and background references, see: Li et al. (2009a ▶,b ▶).

Experimental

Crystal data

C26H22Cl2O4

M = 469.34

Monoclinic,

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)

R int = 0.081

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.160

S = 1.05

5209 reflections

291 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.32 e Å−3

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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810035130/xu5016sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035130/xu5016Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

Nonius KappaCCD diffractometer	3171 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.081
graphite	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 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

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
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)

	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)

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)

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

Table 1

Hydrogen-bond geometry (Å, °)

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) ; (ii) ; (iii) ; (iv) .