Ethyl 4-(2,4-dichloro­phen­yl)-6-(6-meth­oxy-2-naphth­yl)-2-oxocyclo­hex-3-ene-1-carboxyl­ate

Harrison, W.T.A.; Mayekar, A.N.; Yathirajan, H.S.; Narayana, B.; Sarojini, B.K.

doi:10.1107/S1600536810035130

organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page o2478

doi:10.1107/S1600536810035130

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Ethyl 4-(2,4-dichlorophenyl)-6-(6-methoxy-2-naphthyl)-2-oxocyclohex-3-ene-1-carboxylate

William T. A. Harrison,^a ^* A. N. Mayekar,^b,^c H. S. Yathirajan,^b B. Narayana ^d and B. K. Sarojini ^e

^aDepartment of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland, ^bDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, ^cSeQuent Scientific Limited, New Mangalore 575 011, India, ^dDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, India, and ^eDepartment of Chemistry, P. A. College of Engineering, Nadupadavu, Mangalore 574 153, India
^*Correspondence e-mail: w.harrison@abdn.ac.uk

(Received 10 August 2010; accepted 31 August 2010; online 4 September 2010)

In the title compound, C₂₆H₂₂Cl₂O₄, the cyclohexenone 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 intramolecular C—H⋯Cl contact generates an S(6) ring. In the crystal, molecules are linked by C—H⋯O and C—H⋯Cl interactions 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_r = 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)
R_int = 0.081

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.160
S = 1.05
5209 reflections
291 parameters
H-atom parameters constrained
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.32 e Å⁻³

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⋯Cl1^iv	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) $[x, -y+{\script{5\over 2}}, z+{\script{1\over 2}}]$ .

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

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

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

checkCIF report

Comment top

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.

Related literature top

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

Experimental top

(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).

Computing details top

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).

Figures top

Fig. 1. View of the molecular structure of (I) showing 50% displacement ellipsoids (arbitrary spheres for the H atoms).

Ethyl 4-(2,4-dichlorophenyl)-6-(6-methoxy-2-naphthyl)-2-oxocyclohex-3-ene- 1-carboxylate top

Crystal data top

C₂₆H₂₂Cl₂O₄	F(000) = 976
M_r = 469.34	D_x = 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	R_int = 0.081
Graphite monochromator	θ_max = 27.5°, θ_min = 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(F_o²) + (0.0569P)² + 1.4128P] where P = (F_o² + 2F_c²)/3
5209 reflections	(Δ/σ)_max < 0.001
291 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₂₆H₂₂Cl₂O₄	V = 2274.14 (13) Å³
M_r = 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	R_int = 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	Δρ_max = 0.39 e Å⁻³
5209 reflections	Δρ_min = −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	U_iso*/U_eq
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···Cl1^iv	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
M_r	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
R_int	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
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.32

Computer programs: COLLECT (Nonius, 1998), SCALEPACK (Otwinowski & Minor, 1997), DENZO and SCALEPACK (Otwinowski & Minor 1997), and SORTAV (Blessing, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

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···Cl1^iv	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
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
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
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 66| Part 10| October 2010| Page o2478

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Ethyl 4-(2,4-di­chloro­phen­yl)-6-(6-meth­­oxy-2-naphth­yl)-2-oxo­cyclo­hex-3-ene-1-carboxyl­ate

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organic compounds

Ethyl 4-(2,4-dichlorophenyl)-6-(6-methoxy-2-naphthyl)-2-oxocyclohex-3-ene-1-carboxylate