Literature DB >> 22904789

2-[1-(1-Oxoindan-2-yl)eth-yl]indan-1-one.

Abdullah M Asiri, Hassan M Faidallah, Khalid A Alamry, Seik Weng Ng, Edward R T Tiekink.

Abstract

In the title compound, C(20)H(18)O(2), 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 mol-ecule. A three-dimensional architecture arises in the crystal packing owing to C-H⋯O, C-H⋯π and π-π inter-actions [between centrosymmetrically related benzene rings with centroid-centroid distance = 3.7647 (10) Å].

Entities: Chemical Disease Gene

Year: 2012 PMID： 22904789 PMCID： PMC3414182 DOI： 10.1107/S1600536812029315

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

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 = 290.34 Triclinic, 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[F 2 > 2σ(F 2)] = 0.048 wR(F 2) = 0.130 S = 1.05 3299 reflections 199 parameters H-atom parameters constrained Δρmax = 0.29 e Å−3 Δρmin = −0.23 e Å−3 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 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812029315/mw2075sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029315/mw2075Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812029315/mw2075Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

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 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

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	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)

	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)

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)

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

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) ; (ii) .

3 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. Synthesis, antichagasic in vitro evaluation, cytotoxicity assays, molecular modeling and SAR/QSAR studies of a 2-phenyl-3-(1-phenyl-1H-pyrazol-4-yl)-acrylic acid benzylidene-carbohydrazide series.

Authors: Maria A F Vera-Divaio; Antônio C C Freitas; Helena C Castro; Sérgio de Albuquerque; Lucio M Cabral; Carlos R Rodrigues; Magaly G Albuquerque; Rita C A Martins; Maria G M O Henriques; Luiza R S Dias
Journal: Bioorg Med Chem Date: 2008-11-05 Impact factor: 3.641

3. (2E)-2-(Furan-2-yl-methyl-idene)-2,3-dihydro-1H-inden-1-one.

Authors: Abdullah M Asiri; Hassan M Faidallah; Khulud F Al-Nemari; Seik Weng Ng; Edward R T Tiekink
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2012-03-14

3 in total