2-[1-(1-Oxoindan-2-yl)eth­yl]indan-1-one

Asiri, A.M.; Faidallah, H.M.; Alamry, K.A.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536812029315

organic compounds

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ISSN: 2056-9890

Volume 68| Part 8| August 2012| Page o2314

https://doi.org/10.1107/S1600536812029315

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2-[1-(1-Oxoindan-2-yl)ethyl]indan-1-one

Abdullah M. Asiri,^a,^b ‡ Hassan M. Faidallah,^b Khalid A. Alamry,^a,^b Seik Weng Ng ^c and Edward R. T. Tiekink ^c ^*

^aCenter of Excellence for Advanced Materials Research (CEAMR), King Abdulaziz University, PO Box 80203, Jeddah 21589, Saudi Arabia, ^bChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah 21589, Saudi Arabia, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 25 June 2012; accepted 27 June 2012; online 4 July 2012)

In the title compound, C₂₀H₁₈O₂, the fused-ring systems are essentially planar (r.m.s. deviations of the nine fitted atoms = 0.009 and 0.027 Å) and exhibit an orthogonal relationship [dihedral angle = 79.83 (5)°]. To a first approximation, the ketone-O atoms are directed to opposite sides of the molecule. A three-dimensional architecture arises in the crystal packing owing to C—H⋯O, C—H⋯π and π–π interactions [between centrosymmetrically related benzene rings with centroid–centroid distance = 3.7647 (10) Å].

Related literature

For the biological activity of related indan-1-one derivatives, see: Vera-DiVaio et al. (2009 ). For a related structure see: Asiri et al. (2012 ).

Experimental

Crystal data

C₂₀H₁₈O₂
M_r = 290.34
Triclinic, $[P \overline 1]$
a = 7.9225 (6) Å
b = 10.1226 (8) Å
c = 10.3927 (7) Å
α = 103.200 (6)°
β = 103.304 (6)°
γ = 109.462 (7)°
V = 721.25 (9) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.40 × 0.20 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ) T_min = 0.748, T_max = 1.000
4961 measured reflections
3299 independent reflections
2663 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.130
S = 1.05
3299 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C14–C19 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O1ⁱ	1.00	2.55	3.2317 (19)	125
C3—H3⋯Cg1ⁱ	0.95	2.62	3.5395 (17)	163
C11—H11C⋯Cg1ⁱⁱ	0.98	2.99	3.6481 (18)	126
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+2, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812029315/mw2075sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812029315/mw2075Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812029315/mw2075Isup3.cml

checkCIF report

Comment top

The motivation for the synthesis of the title compound, 2-[1-(1-oxo-2,3-dihydro-1H-inden-2-yl)ethyl]-2,3-dihydro-1H-inden-1-one (I), rests with its relationship to biologically active compounds (Vera-DiVaio et al., 2009). Herein, the crystal and molecular structure of (I) is described in continuation of on-going structural studies of indan-1-one derivatives (Asiri et al., 2012).

In (I), Fig. 1, each fused ring system is planar [C1-containing system: r.m.s. deviation of the nine fitted atoms = 0.009 Å with maximum deviation of 0.012 (2) Å for atom C7; C19-containing system: 0.027 Å and 0.044 (2) Å for atom C13]. The dihedral angle between the indan-1-one residues = 79.83 (5)°, indicating an almost orthogonal relationship. To a first approximation the ketone-O atoms are directed to opposite sides of the molecule.

In the crystal packing, molecules are arranged in a three-dimensional architecture by C—H···O and C—H···π interactions, Table 1, as well as π—π contacts between centrosymmetrically related C2–C6 benzene rings [inter-centroid distance = 3.7647 (10) Å for symmetry operation -x, -y, -z], Fig. 2.

Related literature top

For the biological activity of related indan-1-one derivatives, see: Vera-DiVaio et al. (2009). For a related structure see: Asiri et al. (2012).

Experimental top

A solution of acetaldehyde (0.44 g, 0.01 M) in ethanol (20 mL) was added to a stirred solution of 1-indanone (1.3 g,0.01 M) in (20%) ethanolic KOH (20 mL) and stirring was maintained at room temperature for 6 h. The reaction mixture was then poured onto water (200 mL) and set aside overnight. The precipitated solid product was collected by filtration, washed with water, dried and recrystallized from ethanol. M.P.: 413–414 K. Yield: 86%.

Structure description top

For the biological activity of related indan-1-one derivatives, see: Vera-DiVaio et al. (2009). For a related structure see: Asiri et al. (2012).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. A view in projection down the a axis of the unit-cell contents of (I). The C—H···O, C—H···π and π—π interactions are shown as orange, purple and blue dashed lines, respectively.

2-[1-(1-Oxoindan-2-yl)ethyl]indan-1-one top

Crystal data top

C₂₀H₁₈O₂	Z = 2
M_r = 290.34	F(000) = 308
Triclinic, P1	D_x = 1.337 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9225 (6) Å	Cell parameters from 2265 reflections
b = 10.1226 (8) Å	θ = 2.3–27.5°
c = 10.3927 (7) Å	µ = 0.09 mm⁻¹
α = 103.200 (6)°	T = 100 K
β = 103.304 (6)°	Prism, colourless
γ = 109.462 (7)°	0.40 × 0.20 × 0.10 mm
V = 721.25 (9) Å³

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3299 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2663 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.021
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.3°
ω scan	h = −10→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −13→13
T_min = 0.748, T_max = 1.000	l = −13→13
4961 measured reflections

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.130	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0616P)² + 0.1751P] where P = (F_o² + 2F_c²)/3
3299 reflections	(Δ/σ)_max < 0.001
199 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₀H₁₈O₂	γ = 109.462 (7)°
M_r = 290.34	V = 721.25 (9) Å³
Triclinic, P1	Z = 2
a = 7.9225 (6) Å	Mo Kα radiation
b = 10.1226 (8) Å	µ = 0.09 mm⁻¹
c = 10.3927 (7) Å	T = 100 K
α = 103.200 (6)°	0.40 × 0.20 × 0.10 mm
β = 103.304 (6)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3299 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	2663 reflections with I > 2σ(I)
T_min = 0.748, T_max = 1.000	R_int = 0.021
4961 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.130	H-atom parameters constrained
S = 1.05	Δρ_max = 0.29 e Å⁻³
3299 reflections	Δρ_min = −0.23 e Å⁻³
199 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
O1	0.33484 (17)	0.32248 (12)	0.00936 (11)	0.0238 (3)
O2	0.79274 (16)	0.78862 (12)	0.39844 (11)	0.0198 (3)
C1	0.3010 (2)	0.27906 (16)	0.10437 (15)	0.0163 (3)
C2	0.1106 (2)	0.20108 (16)	0.11050 (15)	0.0155 (3)
C3	−0.0656 (2)	0.16295 (17)	0.01190 (16)	0.0187 (3)
H3	−0.0744	0.1886	−0.0711	0.022*
C4	−0.2270 (2)	0.08665 (17)	0.03875 (17)	0.0210 (4)
H4	−0.3488	0.0593	−0.0265	0.025*
C5	−0.2120 (2)	0.04949 (18)	0.16127 (17)	0.0214 (4)
H5	−0.3244	−0.0030	0.1779	0.026*
C6	−0.0367 (2)	0.08758 (17)	0.25916 (17)	0.0195 (3)
H6	−0.0280	0.0619	0.3421	0.023*
C7	0.1266 (2)	0.16466 (16)	0.23241 (16)	0.0160 (3)
C8	0.3313 (2)	0.21549 (18)	0.31939 (16)	0.0187 (3)
H8A	0.3590	0.1297	0.3313	0.022*
H8B	0.3606	0.2859	0.4132	0.022*
C9	0.4496 (2)	0.29281 (16)	0.23705 (15)	0.0159 (3)
H9	0.5224	0.2343	0.2081	0.019*
C10	0.5928 (2)	0.45371 (16)	0.32567 (15)	0.0144 (3)
H10	0.5205	0.5090	0.3618	0.017*
C11	0.7368 (2)	0.45252 (18)	0.45280 (16)	0.0200 (3)
H11A	0.8267	0.5547	0.5091	0.030*
H11B	0.8060	0.3952	0.4201	0.030*
H11C	0.6694	0.4070	0.5101	0.030*
C12	0.6953 (2)	0.53610 (16)	0.23973 (15)	0.0161 (3)
H12	0.5969	0.5394	0.1621	0.019*
C13	0.8140 (2)	0.46661 (17)	0.17407 (16)	0.0190 (3)
H13A	0.8209	0.3838	0.2074	0.023*
H13B	0.7582	0.4284	0.0705	0.023*
C14	1.0084 (2)	0.59087 (16)	0.22124 (15)	0.0155 (3)
C15	1.1668 (2)	0.58854 (17)	0.18552 (16)	0.0183 (3)
H15	1.1600	0.5013	0.1221	0.022*
C16	1.3348 (2)	0.71586 (18)	0.24424 (16)	0.0197 (3)
H16	1.4434	0.7157	0.2201	0.024*
C17	1.3462 (2)	0.84420 (18)	0.33833 (16)	0.0191 (3)
H17	1.4630	0.9296	0.3789	0.023*
C18	1.1889 (2)	0.84811 (17)	0.37301 (16)	0.0169 (3)
H18	1.1957	0.9353	0.4363	0.020*
C19	1.0201 (2)	0.72010 (16)	0.31216 (15)	0.0149 (3)
C20	0.8326 (2)	0.69643 (16)	0.32874 (15)	0.0153 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0241 (6)	0.0235 (6)	0.0171 (5)	0.0014 (5)	0.0050 (5)	0.0092 (5)
O2	0.0198 (6)	0.0187 (6)	0.0208 (6)	0.0077 (5)	0.0085 (5)	0.0046 (5)
C1	0.0184 (8)	0.0119 (7)	0.0156 (7)	0.0037 (6)	0.0052 (6)	0.0038 (6)
C2	0.0155 (8)	0.0116 (7)	0.0170 (7)	0.0044 (6)	0.0046 (6)	0.0031 (6)
C3	0.0201 (8)	0.0154 (7)	0.0175 (7)	0.0062 (6)	0.0028 (6)	0.0047 (6)
C4	0.0155 (8)	0.0192 (8)	0.0226 (8)	0.0054 (7)	0.0016 (6)	0.0040 (7)
C5	0.0154 (8)	0.0204 (8)	0.0257 (8)	0.0041 (6)	0.0086 (7)	0.0059 (7)
C6	0.0188 (8)	0.0198 (8)	0.0203 (7)	0.0062 (7)	0.0083 (6)	0.0081 (7)
C7	0.0160 (8)	0.0133 (7)	0.0175 (7)	0.0055 (6)	0.0053 (6)	0.0038 (6)
C8	0.0152 (8)	0.0199 (8)	0.0206 (7)	0.0043 (6)	0.0056 (6)	0.0103 (7)
C9	0.0141 (7)	0.0155 (7)	0.0183 (7)	0.0047 (6)	0.0064 (6)	0.0070 (6)
C10	0.0136 (7)	0.0151 (7)	0.0139 (7)	0.0045 (6)	0.0050 (6)	0.0052 (6)
C11	0.0167 (8)	0.0238 (8)	0.0193 (7)	0.0064 (7)	0.0050 (6)	0.0104 (7)
C12	0.0145 (8)	0.0159 (7)	0.0151 (7)	0.0029 (6)	0.0051 (6)	0.0050 (6)
C13	0.0200 (8)	0.0156 (7)	0.0198 (7)	0.0038 (6)	0.0107 (6)	0.0038 (6)
C14	0.0175 (8)	0.0152 (7)	0.0147 (7)	0.0054 (6)	0.0063 (6)	0.0073 (6)
C15	0.0224 (8)	0.0186 (8)	0.0201 (7)	0.0108 (7)	0.0106 (7)	0.0102 (7)
C16	0.0165 (8)	0.0267 (8)	0.0213 (7)	0.0116 (7)	0.0080 (6)	0.0120 (7)
C17	0.0134 (8)	0.0205 (8)	0.0191 (7)	0.0040 (6)	0.0020 (6)	0.0069 (7)
C18	0.0161 (8)	0.0167 (7)	0.0160 (7)	0.0054 (6)	0.0039 (6)	0.0054 (6)
C19	0.0143 (8)	0.0164 (7)	0.0144 (7)	0.0053 (6)	0.0042 (6)	0.0076 (6)
C20	0.0156 (8)	0.0164 (7)	0.0130 (7)	0.0046 (6)	0.0040 (6)	0.0070 (6)

Geometric parameters (Å, º) top

O1—C1	1.2172 (18)	C10—H10	1.0000
O2—C20	1.2200 (18)	C11—H11A	0.9800
C1—C2	1.475 (2)	C11—H11B	0.9800
C1—C9	1.537 (2)	C11—H11C	0.9800
C2—C7	1.388 (2)	C12—C20	1.532 (2)
C2—C3	1.397 (2)	C12—C13	1.537 (2)
C3—C4	1.383 (2)	C12—H12	1.0000
C3—H3	0.9500	C13—C14	1.508 (2)
C4—C5	1.399 (2)	C13—H13A	0.9900
C4—H4	0.9500	C13—H13B	0.9900
C5—C6	1.388 (2)	C14—C19	1.388 (2)
C5—H5	0.9500	C14—C15	1.394 (2)
C6—C7	1.397 (2)	C15—C16	1.389 (2)
C6—H6	0.9500	C15—H15	0.9500
C7—C8	1.506 (2)	C16—C17	1.398 (2)
C8—C9	1.552 (2)	C16—H16	0.9500
C8—H8A	0.9900	C17—C18	1.384 (2)
C8—H8B	0.9900	C17—H17	0.9500
C9—C10	1.546 (2)	C18—C19	1.396 (2)
C9—H9	1.0000	C18—H18	0.9500
C10—C11	1.539 (2)	C19—C20	1.481 (2)
C10—C12	1.541 (2)

O1—C1—C2	125.93 (14)	C10—C11—H11A	109.5
O1—C1—C9	125.80 (14)	C10—C11—H11B	109.5
C2—C1—C9	108.26 (12)	H11A—C11—H11B	109.5
C7—C2—C3	121.93 (15)	C10—C11—H11C	109.5
C7—C2—C1	109.99 (13)	H11A—C11—H11C	109.5
C3—C2—C1	128.07 (14)	H11B—C11—H11C	109.5
C4—C3—C2	117.95 (14)	C20—C12—C13	105.56 (12)
C4—C3—H3	121.0	C20—C12—C10	111.74 (12)
C2—C3—H3	121.0	C13—C12—C10	115.59 (12)
C3—C4—C5	120.44 (15)	C20—C12—H12	107.9
C3—C4—H4	119.8	C13—C12—H12	107.9
C5—C4—H4	119.8	C10—C12—H12	107.9
C6—C5—C4	121.51 (15)	C14—C13—C12	105.17 (12)
C6—C5—H5	119.2	C14—C13—H13A	110.7
C4—C5—H5	119.2	C12—C13—H13A	110.7
C5—C6—C7	118.21 (14)	C14—C13—H13B	110.7
C5—C6—H6	120.9	C12—C13—H13B	110.7
C7—C6—H6	120.9	H13A—C13—H13B	108.8
C2—C7—C6	119.95 (14)	C19—C14—C15	119.78 (14)
C2—C7—C8	111.50 (14)	C19—C14—C13	111.79 (14)
C6—C7—C8	128.54 (14)	C15—C14—C13	128.43 (14)
C7—C8—C9	105.61 (12)	C16—C15—C14	118.87 (15)
C7—C8—H8A	110.6	C16—C15—H15	120.6
C9—C8—H8A	110.6	C14—C15—H15	120.6
C7—C8—H8B	110.6	C15—C16—C17	120.85 (15)
C9—C8—H8B	110.6	C15—C16—H16	119.6
H8A—C8—H8B	108.8	C17—C16—H16	119.6
C1—C9—C10	114.59 (12)	C18—C17—C16	120.66 (15)
C1—C9—C8	104.64 (12)	C18—C17—H17	119.7
C10—C9—C8	112.64 (13)	C16—C17—H17	119.7
C1—C9—H9	108.2	C17—C18—C19	118.06 (14)
C10—C9—H9	108.2	C17—C18—H18	121.0
C8—C9—H9	108.2	C19—C18—H18	121.0
C11—C10—C12	110.83 (12)	C14—C19—C18	121.75 (15)
C11—C10—C9	109.67 (12)	C14—C19—C20	109.52 (13)
C12—C10—C9	112.68 (12)	C18—C19—C20	128.74 (14)
C11—C10—H10	107.8	O2—C20—C19	126.32 (14)
C12—C10—H10	107.8	O2—C20—C12	125.82 (14)
C9—C10—H10	107.8	C19—C20—C12	107.85 (12)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C14–C19 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1ⁱ	1.00	2.55	3.2317 (19)	125
C3—H3···Cg1ⁱ	0.95	2.62	3.5395 (17)	163
C11—H11C···Cg1ⁱⁱ	0.98	2.99	3.6481 (18)	126

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₈O₂
M_r	290.34
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.9225 (6), 10.1226 (8), 10.3927 (7)
α, β, γ (°)	103.200 (6), 103.304 (6), 109.462 (7)
V (Å³)	721.25 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.40 × 0.20 × 0.10

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2012)
T_min, T_max	0.748, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	4961, 3299, 2663
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.130, 1.05
No. of reflections	3299
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.23

Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C14–C19 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1ⁱ	1.00	2.55	3.2317 (19)	125
C3—H3···Cg1ⁱ	0.95	2.62	3.5395 (17)	163
C11—H11C···Cg1ⁱⁱ	0.98	2.99	3.6481 (18)	126

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

Footnotes

‡Additional correspondence author, e-mail: aasiri2@kau.edu.sa.

Acknowledgements

The authors are grateful to King Abdulaziz University for providing research facilities. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12).

References

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