Ethyl 4-(4-bromo­phen­yl)-6-(4-ethoxy­phen­yl)-2-oxocyclo­hex-3-enecarboxyl­ate

Badshah, A.; Hasan, A.; Barbarín, C.R.

doi:10.1107/S1600536809003523

organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o467

doi:10.1107/S1600536809003523

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Ethyl 4-(4-bromophenyl)-6-(4-ethoxyphenyl)-2-oxocyclohex-3-enecarboxylate

Amir Badshah,^a Aurangzeb Hasan ^a ^* and Cecilia R. Barbarín ^b

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and ^bDivisión de Estudios de Posgrado, Facultad de Ciencias Químicas, UANL, Guerreo y Progreso S/N, Col. Treviño, CP, 64570 Monterrey, NL, Mexico
^*Correspondence e-mail: h.aurangzeb@yahoo.com

(Received 27 December 2008; accepted 28 January 2009; online 6 February 2009)

The title compound, C₂₃H₂₃BrO₄, is an intermediate in the synthesis of fused heterocycles. In the title molecule, the cyclohexene ring has a distorted half-chair conformation. The bromophenyl ring and the mean plane of the cyclohexene ring form a dihedral angle of 13.8 (3)°, whereas the benzene and cyclohexene rings are approximately perpendicular [88.44 (17)°]. There are only weak C—H⋯O and C—H⋯π intermolecular interactions.

Related literature

For applications of cyclohexenones, see: Eddington et al. (2000 ); Li & Strobel (2001 ); Luu et al. (2000 ); Padmavathi et al. (2000 , 2001 ).

Experimental

Crystal data

C₂₃H₂₃BrO₄
M_r = 443.32
Monoclinic, P 2₁ /c
a = 12.792 (4) Å
b = 14.537 (4) Å
c = 12.114 (4) Å
β = 113.88 (2)°
V = 2059.8 (11) Å³
Z = 4
Mo Kα radiation
μ = 2.02 mm⁻¹
T = 298 (2) K
0.50 × 0.50 × 0.08 mm

Data collection

Bruker P4 diffractometer
Absorption correction: gaussian (XSCANS; Bruker, 1999 ) T_min = 0.246, T_max = 0.941
7765 measured reflections
3630 independent reflections
2088 reflections with I > 2σ(I)
R_int = 0.054
3 standard reflections every 97 reflections intensity decay: 6.4%

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.175
S = 1.01
3630 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯O1ⁱ	0.93	2.42	3.163 (6)	137
C8—H8A⋯O2ⁱⁱ	0.97	2.59	3.244 (6)	125
C15—H15B⋯O2	0.96	2.58	3.062 (13)	111
C23—H23A⋯Cgⁱⁱⁱ	0.96	2.90	3.741 (6)	147
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) -x+1, -y+1, -z.

Data collection: XSCANS (Bruker, 1999); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL-Plus (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL-Plus; molecular graphics: SHELXTL-Plus and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXTL-Plus.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809003523/gk2184sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809003523/gk2184Isup2.hkl

checkCIF report

Comment top

Cyclohexenones are either prepared from natural sources or entirely via synthetic routes. The reason for their preparation is a variety of medical effects. The molecules provide anticonvulsant, antimalarial, antiinflamatory and cardiovascular effects (Eddington et al., 2000). Cyclohexenones are also important intermediates for many biologically active compounds (Padmavathi et al., 2001; Padmavathi et al., 2000). A series of novel compounds have been synthesized, known as cyclohexenoic long chain fatty alcohols, which are used in the treatment of neurological disorders (Luu et al., 2000). A number of their derivatives have fungicidal and antitumor activities (Li & Strobel, 2001).

In the title compound, C₂₃H₂₃BrO₄ (Scheme 1, Fig. 1), the two rings, i.e. bromophenyl [C1-C6] and the cyclohexene [C7-C12], are slightly twisted' with the dihedral angle of 13.8 (3)°. Cyclohexene [C7- C12], is approximately perpendicular to the benzene ring [C16-C21] [88.44 (17)°]. The title molecule has two asymmetric carbon atoms C9 and C12 that are in RS and SR configurations, respectively. The comformation of the cyclohexene ring is distorted half chair [Θ = 50.6 (10) and Φ = 138.9 (13)°, compared with the ideal values of Θ = 50.0 and Φ = 150.0°].

As indicated by intermolecular contacts. there are only weak intermolecular interactions X—H···O and C—H···π (Table 1). The crystal packing is shown in Fig. 2.

Related literature top

For applications of cyclohexenones, see: Eddington et al. (2000); Li & Strobel (2001); Luu et al. (2000); Padmavathi et al. (2000, 2001).

Experimental top

Ethyl 4-(4-bromophenyl)-6-(4-ethoxyphenyl)-2-oxocyclhex-3-enecarboxylate was synthesized by refluxing ethyl acetoacetate (0.39 g, 0.40 ml, 3 mmol) with 1-(4-bromophenyl)-3-(4-ethoxyphenyl) prop-2-ene-1-one (3 mmol, 0.990 g) for 2 h in 10–15 ml of ethanol in presence of 0.5 ml 10% NaOH. The reaction mixture was then poured while having been stirred intensively into 200 ml of ice-cold water. The mixture was kept at room temperature until the reaction product separated as a solid, which was filtered off and recrystallized from ethanol (yield 65%, m.p. 400 K).

Computing details top

Data collection: XSCANS (Bruker, 1999); cell refinement: XSCANS (Bruker, 1999); data reduction: XSCANS (Bruker, 1999); program(s) used to solve structure: SHELXTL-Plus (Sheldrick, 2008); program(s) used to refine structure: SHELXTL-Plus (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL-Plus (Sheldrick, 2008).

Figures top

	Fig. 1. The title molecule with the atom labeling scheme. The displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. The packing diagram of the title compound, viewed along the c axis showing weak C—H···O and C—H···π interactions

Ethyl 4-(4-bromophenyl)-6-(4-ethoxyphenyl)-2-oxocyclohex-3-enecarboxylate top

Crystal data top

C₂₃H₂₃BrO₄	F(000) = 912
M_r = 443.32	D_x = 1.430 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 400 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 12.792 (4) Å	Cell parameters from 91 reflections
b = 14.537 (4) Å	θ = 4.6–12.4°
c = 12.114 (4) Å	µ = 2.02 mm⁻¹
β = 113.88 (2)°	T = 298 K
V = 2059.8 (11) Å³	Plate, colourless
Z = 4	0.50 × 0.50 × 0.08 mm

Data collection top

Bruker P4 diffractometer	2088 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.054
Graphite monochromator	θ_max = 25.0°, θ_min = 2.2°
ω scans	h = −14→15
Absorption correction: gaussian (XSCANS; Bruker, 1999)	k = −1→17
T_min = 0.246, T_max = 0.941	l = −14→14
7765 measured reflections	3 standard reflections every 97 reflections
3630 independent reflections	intensity decay: 6.4%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.059	H-atom parameters constrained
wR(F²) = 0.175	w = 1/[σ²(F_o²) + (0.0744P)² + 1.4731P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
3630 reflections	Δρ_max = 0.44 e Å⁻³
254 parameters	Δρ_min = −0.41 e Å⁻³
0 restraints	Extinction correction: SHELXTL-Plus (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0050 (10)

Crystal data top

C₂₃H₂₃BrO₄	V = 2059.8 (11) Å³
M_r = 443.32	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.792 (4) Å	µ = 2.02 mm⁻¹
b = 14.537 (4) Å	T = 298 K
c = 12.114 (4) Å	0.50 × 0.50 × 0.08 mm
β = 113.88 (2)°

Data collection top

Bruker P4 diffractometer	2088 reflections with I > 2σ(I)
Absorption correction: gaussian (XSCANS; Bruker, 1999)	R_int = 0.054
T_min = 0.246, T_max = 0.941	3 standard reflections every 97 reflections
7765 measured reflections	intensity decay: 6.4%
3630 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.175	H-atom parameters constrained
S = 1.01	Δρ_max = 0.44 e Å⁻³
3630 reflections	Δρ_min = −0.41 e Å⁻³
254 parameters

Special details top

Experimental. Absorption correction based on 6 crystal faces Faces used: 001, 00–1, 20–1, -201, 010, 0–10

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
Br1	0.12714 (6)	0.10565 (5)	1.01969 (7)	0.1061 (4)
O1	0.5590 (3)	0.4373 (2)	0.7177 (4)	0.0864 (11)
O2	0.6752 (4)	0.3470 (3)	0.5468 (4)	0.1049 (13)
O3	0.7863 (4)	0.3351 (3)	0.7398 (4)	0.0901 (11)
O4	0.8559 (3)	−0.0461 (2)	0.5587 (3)	0.0662 (9)
C1	0.2279 (4)	0.1456 (4)	0.9511 (5)	0.0673 (13)
C2	0.2177 (5)	0.2318 (4)	0.9038 (5)	0.0777 (15)
H2A	0.1619	0.2715	0.9068	0.093*
C3	0.2889 (4)	0.2597 (3)	0.8525 (5)	0.0700 (13)
H3A	0.2809	0.3185	0.8200	0.084*
C4	0.3099 (4)	0.0866 (3)	0.9484 (5)	0.0687 (13)
H4A	0.3174	0.0281	0.9818	0.082*
C5	0.3812 (4)	0.1153 (3)	0.8955 (5)	0.0635 (12)
H5A	0.4362	0.0749	0.8922	0.076*
C6	0.3739 (4)	0.2020 (3)	0.8474 (4)	0.0534 (11)
C7	0.4524 (4)	0.2326 (3)	0.7936 (4)	0.0523 (10)
C8	0.5179 (4)	0.1615 (3)	0.7592 (4)	0.0591 (12)
H8A	0.5465	0.1162	0.8234	0.071*
H8B	0.4660	0.1302	0.6871	0.071*
C9	0.6161 (5)	0.1980 (3)	0.7360 (6)	0.0819 (16)
H9A	0.6733	0.2120	0.8171	0.098*
C10	0.4667 (4)	0.3220 (3)	0.7762 (5)	0.0649 (13)
H10A	0.4249	0.3647	0.7988	0.078*
C11	0.5422 (4)	0.3557 (3)	0.7250 (5)	0.0664 (13)
C12	0.5970 (5)	0.2855 (3)	0.6760 (6)	0.0923 (19)
H12A	0.5368	0.2717	0.5965	0.111*
C13	0.6893 (5)	0.3258 (3)	0.6454 (7)	0.0745 (15)
C14	0.8792 (5)	0.3710 (5)	0.7141 (8)	0.122 (3)
H14A	0.9372	0.3963	0.7873	0.147*
H14B	0.8510	0.4203	0.6554	0.147*
C15	0.9299 (8)	0.2991 (7)	0.6667 (11)	0.176 (4)
H15A	0.9915	0.3247	0.6506	0.264*
H15B	0.8728	0.2748	0.5934	0.264*
H15C	0.9587	0.2506	0.7251	0.264*
C16	0.6757 (5)	0.1277 (3)	0.6896 (5)	0.0666 (13)
C17	0.6243 (4)	0.0920 (4)	0.5765 (6)	0.0792 (15)
H17A	0.5488	0.1082	0.5298	0.095*
C18	0.6789 (4)	0.0329 (4)	0.5277 (5)	0.0737 (14)
H18A	0.6411	0.0099	0.4499	0.088*
C19	0.7853 (5)	0.0997 (3)	0.7578 (5)	0.0791 (15)
H19A	0.8221	0.1205	0.8368	0.095*
C20	0.8414 (5)	0.0416 (4)	0.7115 (5)	0.0747 (14)
H20A	0.9160	0.0240	0.7593	0.090*
C21	0.7896 (4)	0.0092 (3)	0.5964 (4)	0.0574 (11)
C22	0.8162 (5)	−0.0624 (4)	0.4328 (5)	0.0775 (14)
H22A	0.7985	−0.0046	0.3891	0.093*
H22B	0.7475	−0.0997	0.4051	0.093*
C23	0.9080 (5)	−0.1110 (4)	0.4114 (6)	0.0858 (17)
H23A	0.8839	−0.1220	0.3265	0.129*
H23B	0.9237	−0.1687	0.4536	0.129*
H23C	0.9759	−0.0739	0.4402	0.129*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.1224 (6)	0.1085 (6)	0.1275 (7)	−0.0075 (4)	0.0918 (5)	−0.0037 (4)
O1	0.107 (3)	0.0405 (19)	0.126 (3)	−0.0019 (18)	0.061 (2)	0.0037 (19)
O2	0.105 (3)	0.111 (3)	0.100 (3)	−0.012 (3)	0.042 (3)	0.002 (3)
O3	0.085 (3)	0.084 (3)	0.100 (3)	−0.009 (2)	0.036 (3)	0.000 (2)
O4	0.068 (2)	0.065 (2)	0.072 (2)	0.0053 (16)	0.0340 (18)	−0.0070 (17)
C1	0.076 (3)	0.067 (3)	0.072 (3)	−0.006 (3)	0.043 (3)	−0.012 (3)
C2	0.085 (4)	0.072 (4)	0.093 (4)	0.016 (3)	0.054 (3)	−0.005 (3)
C3	0.080 (3)	0.054 (3)	0.086 (4)	0.012 (2)	0.044 (3)	0.003 (2)
C4	0.075 (3)	0.051 (3)	0.086 (4)	0.000 (2)	0.039 (3)	0.001 (2)
C5	0.062 (3)	0.051 (3)	0.084 (4)	0.002 (2)	0.037 (3)	−0.005 (2)
C6	0.060 (3)	0.041 (2)	0.061 (3)	0.004 (2)	0.025 (2)	−0.005 (2)
C7	0.057 (3)	0.041 (2)	0.058 (3)	0.0010 (19)	0.022 (2)	−0.003 (2)
C8	0.065 (3)	0.042 (2)	0.078 (3)	−0.005 (2)	0.037 (3)	−0.003 (2)
C9	0.106 (4)	0.048 (3)	0.124 (5)	0.007 (3)	0.080 (4)	0.005 (3)
C10	0.067 (3)	0.050 (3)	0.083 (4)	0.003 (2)	0.036 (3)	−0.004 (2)
C11	0.071 (3)	0.047 (3)	0.079 (4)	0.000 (2)	0.028 (3)	0.000 (2)
C12	0.111 (4)	0.049 (3)	0.153 (6)	−0.006 (3)	0.091 (4)	0.003 (3)
C13	0.081 (4)	0.052 (3)	0.101 (5)	−0.010 (3)	0.048 (4)	−0.006 (3)
C14	0.065 (4)	0.109 (5)	0.189 (8)	−0.015 (4)	0.046 (5)	−0.004 (5)
C15	0.128 (7)	0.185 (9)	0.266 (12)	0.007 (7)	0.133 (8)	0.023 (9)
C16	0.089 (4)	0.047 (3)	0.082 (4)	−0.006 (3)	0.053 (3)	−0.001 (3)
C17	0.057 (3)	0.084 (4)	0.099 (4)	0.010 (3)	0.033 (3)	0.003 (3)
C18	0.061 (3)	0.080 (3)	0.079 (4)	−0.001 (3)	0.027 (3)	−0.014 (3)
C19	0.095 (4)	0.074 (3)	0.072 (4)	0.018 (3)	0.038 (3)	0.002 (3)
C20	0.073 (3)	0.077 (3)	0.068 (4)	0.016 (3)	0.022 (3)	−0.004 (3)
C21	0.068 (3)	0.049 (2)	0.063 (3)	−0.002 (2)	0.034 (3)	0.001 (2)
C22	0.081 (3)	0.081 (3)	0.079 (4)	−0.006 (3)	0.041 (3)	−0.016 (3)
C23	0.094 (4)	0.090 (4)	0.091 (4)	−0.013 (3)	0.056 (3)	−0.027 (3)

Geometric parameters (Å, º) top

Br1—C1	1.886 (5)	C10—H10A	0.9300
O1—C11	1.216 (6)	C11—C12	1.490 (7)
O2—C13	1.176 (7)	C12—C13	1.493 (7)
O3—C13	1.311 (7)	C12—H12A	0.9800
O3—C14	1.442 (7)	C14—C15	1.465 (11)
O4—C21	1.374 (5)	C14—H14A	0.9700
O4—C22	1.419 (6)	C14—H14B	0.9700
C1—C2	1.361 (7)	C15—H15A	0.9600
C1—C4	1.366 (7)	C15—H15B	0.9600
C2—C3	1.357 (7)	C15—H15C	0.9600
C2—H2A	0.9300	C16—C17	1.360 (8)
C3—C6	1.393 (6)	C16—C19	1.370 (7)
C3—H3A	0.9300	C17—C18	1.382 (7)
C4—C5	1.375 (7)	C17—H17A	0.9300
C4—H4A	0.9300	C18—C21	1.365 (7)
C5—C6	1.375 (6)	C18—H18A	0.9300
C5—H5A	0.9300	C19—C20	1.366 (7)
C6—C7	1.470 (6)	C19—H19A	0.9300
C7—C10	1.342 (6)	C20—C21	1.363 (7)
C7—C8	1.492 (6)	C20—H20A	0.9300
C8—C9	1.492 (6)	C22—C23	1.480 (7)
C8—H8A	0.9700	C22—H22A	0.9700
C8—H8B	0.9700	C22—H22B	0.9700
C9—C12	1.436 (7)	C23—H23A	0.9600
C9—C16	1.512 (6)	C23—H23B	0.9600
C9—H9A	0.9800	C23—H23C	0.9600
C10—C11	1.429 (7)

C13—O3—C14	114.9 (5)	C13—C12—H12A	102.8
C21—O4—C22	117.1 (4)	O2—C13—O3	124.1 (5)
C2—C1—C4	120.8 (5)	O2—C13—C12	123.0 (7)
C2—C1—Br1	120.2 (4)	O3—C13—C12	112.9 (6)
C4—C1—Br1	119.1 (4)	O3—C14—C15	111.2 (6)
C3—C2—C1	120.0 (5)	O3—C14—H14A	109.4
C3—C2—H2A	120.0	C15—C14—H14A	109.4
C1—C2—H2A	120.0	O3—C14—H14B	109.4
C2—C3—C6	121.4 (5)	C15—C14—H14B	109.4
C2—C3—H3A	119.3	H14A—C14—H14B	108.0
C6—C3—H3A	119.3	C14—C15—H15A	109.5
C1—C4—C5	118.8 (5)	C14—C15—H15B	109.5
C1—C4—H4A	120.6	H15A—C15—H15B	109.5
C5—C4—H4A	120.6	C14—C15—H15C	109.5
C4—C5—C6	122.1 (4)	H15A—C15—H15C	109.5
C4—C5—H5A	119.0	H15B—C15—H15C	109.5
C6—C5—H5A	119.0	C17—C16—C19	116.9 (5)
C5—C6—C3	117.0 (4)	C17—C16—C9	121.4 (5)
C5—C6—C7	121.5 (4)	C19—C16—C9	121.6 (5)
C3—C6—C7	121.5 (4)	C16—C17—C18	123.1 (5)
C10—C7—C6	121.6 (4)	C16—C17—H17A	118.4
C10—C7—C8	120.0 (4)	C18—C17—H17A	118.4
C6—C7—C8	118.5 (4)	C21—C18—C17	118.4 (5)
C9—C8—C7	114.7 (4)	C21—C18—H18A	120.8
C9—C8—H8A	108.6	C17—C18—H18A	120.8
C7—C8—H8A	108.6	C20—C19—C16	121.1 (5)
C9—C8—H8B	108.6	C20—C19—H19A	119.5
C7—C8—H8B	108.6	C16—C19—H19A	119.5
H8A—C8—H8B	107.6	C21—C20—C19	121.0 (5)
C12—C9—C8	115.2 (4)	C21—C20—H20A	119.5
C12—C9—C16	114.7 (4)	C19—C20—H20A	119.5
C8—C9—C16	114.8 (4)	C20—C21—C18	119.4 (4)
C12—C9—H9A	103.2	C20—C21—O4	115.7 (4)
C8—C9—H9A	103.2	C18—C21—O4	124.9 (4)
C16—C9—H9A	103.2	O4—C22—C23	107.7 (4)
C7—C10—C11	124.0 (4)	O4—C22—H22A	110.2
C7—C10—H10A	118.0	C23—C22—H22A	110.2
C11—C10—H10A	118.0	O4—C22—H22B	110.2
O1—C11—C10	122.4 (5)	C23—C22—H22B	110.2
O1—C11—C12	121.0 (4)	H22A—C22—H22B	108.5
C10—C11—C12	116.6 (4)	C22—C23—H23A	109.5
C9—C12—C11	114.6 (5)	C22—C23—H23B	109.5
C9—C12—C13	118.9 (5)	H23A—C23—H23B	109.5
C11—C12—C13	112.1 (4)	C22—C23—H23C	109.5
C9—C12—H12A	102.8	H23A—C23—H23C	109.5
C11—C12—H12A	102.8	H23B—C23—H23C	109.5

C4—C1—C2—C3	0.5 (9)	C10—C11—C12—C9	−30.2 (8)
Br1—C1—C2—C3	−178.7 (4)	O1—C11—C12—C13	12.5 (8)
C1—C2—C3—C6	−0.4 (9)	C10—C11—C12—C13	−169.7 (5)
C2—C1—C4—C5	−0.9 (8)	C14—O3—C13—O2	−2.3 (8)
Br1—C1—C4—C5	178.3 (4)	C14—O3—C13—C12	178.0 (5)
C1—C4—C5—C6	1.2 (8)	C9—C12—C13—O2	123.8 (7)
C4—C5—C6—C3	−1.2 (7)	C11—C12—C13—O2	−98.6 (7)
C4—C5—C6—C7	178.6 (4)	C9—C12—C13—O3	−56.5 (7)
C2—C3—C6—C5	0.7 (8)	C11—C12—C13—O3	81.1 (6)
C2—C3—C6—C7	−179.0 (5)	C13—O3—C14—C15	−79.5 (8)
C5—C6—C7—C10	−162.0 (5)	C12—C9—C16—C17	−66.9 (7)
C3—C6—C7—C10	17.7 (7)	C8—C9—C16—C17	70.0 (7)
C5—C6—C7—C8	17.5 (6)	C12—C9—C16—C19	110.6 (6)
C3—C6—C7—C8	−162.8 (5)	C8—C9—C16—C19	−112.4 (6)
C10—C7—C8—C9	14.6 (7)	C19—C16—C17—C18	−2.6 (8)
C6—C7—C8—C9	−164.8 (4)	C9—C16—C17—C18	175.1 (5)
C7—C8—C9—C12	−37.7 (7)	C16—C17—C18—C21	0.1 (8)
C7—C8—C9—C16	−174.4 (5)	C17—C16—C19—C20	2.8 (8)
C6—C7—C10—C11	179.6 (4)	C9—C16—C19—C20	−174.8 (5)
C8—C7—C10—C11	0.2 (8)	C16—C19—C20—C21	−0.6 (8)
C7—C10—C11—O1	−175.0 (5)	C19—C20—C21—C18	−2.0 (8)
C7—C10—C11—C12	7.3 (8)	C19—C20—C21—O4	177.9 (4)
C8—C9—C12—C11	45.5 (8)	C17—C18—C21—C20	2.2 (7)
C16—C9—C12—C11	−177.8 (5)	C17—C18—C21—O4	−177.6 (4)
C8—C9—C12—C13	−178.0 (5)	C22—O4—C21—C20	−164.8 (4)
C16—C9—C12—C13	−41.2 (9)	C22—O4—C21—C18	15.0 (6)
O1—C11—C12—C9	152.0 (6)	C21—O4—C22—C23	171.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O1ⁱ	0.93	2.42	3.163 (6)	137
C8—H8A···O2ⁱⁱ	0.97	2.59	3.244 (6)	125
C15—H15B···O2	0.96	2.58	3.062 (13)	111
C23—H23A···Cgⁱⁱⁱ	0.96	2.90	3.741 (6)	147

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x, −y+1/2, z+1/2; (iii) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₃H₂₃BrO₄
M_r	443.32
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	12.792 (4), 14.537 (4), 12.114 (4)
β (°)	113.88 (2)
V (Å³)	2059.8 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.02
Crystal size (mm)	0.50 × 0.50 × 0.08

Data collection
Diffractometer	Bruker P4 diffractometer
Absorption correction	Gaussian (XSCANS; Bruker, 1999)
T_min, T_max	0.246, 0.941
No. of measured, independent and observed [I > 2σ(I)] reflections	7765, 3630, 2088
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.175, 1.01
No. of reflections	3630
No. of parameters	254
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.41

Computer programs: XSCANS (Bruker, 1999), SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O1ⁱ	0.93	2.42	3.163 (6)	137
C8—H8A···O2ⁱⁱ	0.97	2.59	3.244 (6)	125
C15—H15B···O2	0.96	2.58	3.062 (13)	111
C23—H23A···Cgⁱⁱⁱ	0.96	2.90	3.741 (6)	147

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x, −y+1/2, z+1/2; (iii) −x+1, −y+1, −z.

Acknowledgements

AB is grateful to the Higher Education Commission of Pakistan for a PhD scholarship.

References

Bruker (1999). XSCANS Users Manual. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Eddington, N. D., Cox, D. S., Roberts, R. R., Stables, J. P., Powell, C. B. & Scott, A. R. (2000). Curr. Med. Chem. 7, 417–436. Web of Science CrossRef PubMed CAS Google Scholar
Li, J. Y. & Strobel, G. A. (2001). Phytochemistry, 57, 261–265. Web of Science CrossRef PubMed CAS Google Scholar
Luu, B., Aguilar, J. L. G. D. & Junges, C. G. (2000). Molecules, 5, 1439–1460. Web of Science CrossRef CAS Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CrossRef CAS IUCr Journals Google Scholar
Padmavathi, V., Reddy, B. J. M., Balaiah, A., Reddy, K. V. & Reddy, D. B. (2000). Molecules, 5, 1281–1286. Web of Science CrossRef CAS Google Scholar
Padmavathi, V., Sharmila, K., Reddy, A. S. & Reddy, D. B. (2001). Indian J. Chem. Sect. B, 40, 11–14. 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 65| Part 3| March 2009| Page o467

doi:10.1107/S1600536809003523

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Ethyl 4-(4-bromo­phen­yl)-6-(4-eth­oxy­phen­yl)-2-oxo­cyclo­hex-3-ene­carboxyl­ate

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Experimental

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References

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Ethyl 4-(4-bromophenyl)-6-(4-ethoxyphenyl)-2-oxocyclohex-3-enecarboxylate