Literature DB >> 22589932

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

Abdullah M Asiri, Hassan M Faidallah, Khulud F Al-Nemari, Seik Weng Ng, Edward R T Tiekink.

Abstract

In the title compound, C(14)H(10)O(2), the five-membered ring of the inden-1-one residue is almost planar (r.m.s. deviation = 0.035 Å). A twist about the single bond linking the two residues is evident [C-C-C-C torsion angle = -13.2 (5)°]. The three-dimensional architecture is stabilized by C-H⋯O (involving the trifurcated carbonyl O atom), C-H⋯π and π-π inter-actions [between the five- and six-membered rings of inden-1-one residues; ring centroid-centroid distance = 3.7983 (17) Å]. The sample studied was a non-merohedral twin; the minor component refined to approximately 36%.

Entities: Chemical Disease Gene

Year: 2012 PMID： 22589932 PMCID： PMC3344023 DOI： 10.1107/S1600536812010501

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

Related literature

For the biological activity of related species, see: Vera-DiVaio et al. (2009 ▶). For related structures, see: Asiri et al. (2012a ▶,b ▶). For the treatment of twinned data, see: Spek (2009 ▶).

Experimental

Crystal data

C14H10O2 M = 210.22 Monoclinic, a = 5.9333 (8) Å b = 7.6605 (6) Å c = 22.386 (3) Å β = 91.582 (14)° V = 1017.1 (2) Å3 Z = 4 Mo Kα radiation μ = 0.09 mm−1 T = 100 K 0.25 × 0.25 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.978, T max = 0.995 5052 measured reflections 3274 independent reflections 2683 reflections with I > 2σ(I) R int = 0.086

Refinement

R[F 2 > 2σ(F 2)] = 0.081 wR(F 2) = 0.251 S = 1.10 3274 reflections 146 parameters H-atom parameters constrained Δρmax = 0.49 e Å−3 Δρmin = −0.38 e Å−3 Data collection: CrysAlis PRO (Agilent, 2011 ▶); 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 (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/S1600536812010501/bt5838sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010501/bt5838Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812010501/bt5838Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₄H₁₀O₂	F(000) = 440
M_r = 210.22	D_x = 1.373 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1169 reflections
a = 5.9333 (8) Å	θ = 2.7–27.5°
b = 7.6605 (6) Å	µ = 0.09 mm⁻¹
c = 22.386 (3) Å	T = 100 K
β = 91.582 (14)°	Plate, light-brown
V = 1017.1 (2) Å³	0.25 × 0.25 × 0.05 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	3274 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2683 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.086
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.8°
ω scan	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −9→9
T_min = 0.978, T_max = 0.995	l = −28→29
5052 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)] = 0.081	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.251	H-atom parameters constrained
S = 1.10	w = 1/[σ²(F_o²) + (0.1697P)² + 0.358P] where P = (F_o² + 2F_c²)/3
3274 reflections	(Δ/σ)_max = 0.001
146 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³

	x	y	z	U_iso*/U_eq
O1	0.8036 (3)	0.1044 (3)	0.41473 (10)	0.0225 (5)
O2	0.3114 (4)	0.3830 (3)	0.25105 (10)	0.0247 (6)
C1	0.6426 (5)	0.1749 (3)	0.43739 (13)	0.0158 (6)
C2	0.6084 (5)	0.2043 (3)	0.50122 (13)	0.0165 (6)
C3	0.7489 (5)	0.1602 (4)	0.55034 (14)	0.0198 (6)
H3	0.8888	0.1028	0.5449	0.024*
C4	0.6783 (5)	0.2028 (4)	0.60685 (14)	0.0248 (7)
H4	0.7724	0.1762	0.6406	0.030*
C5	0.4707 (6)	0.2842 (4)	0.61507 (14)	0.0249 (7)
H5	0.4248	0.3100	0.6544	0.030*
C6	0.3307 (5)	0.3279 (4)	0.56689 (14)	0.0217 (7)
H6	0.1902	0.3840	0.5727	0.026*
C7	0.4012 (5)	0.2875 (3)	0.50936 (14)	0.0174 (6)
C8	0.2794 (5)	0.3192 (4)	0.44983 (13)	0.0173 (6)
H8A	0.1365	0.2526	0.4469	0.021*
H8B	0.2464	0.4448	0.4439	0.021*
C9	0.4447 (5)	0.2549 (3)	0.40530 (14)	0.0171 (6)
C10	0.4384 (5)	0.2705 (4)	0.34539 (14)	0.0176 (6)
H10	0.5628	0.2246	0.3247	0.021*
C11	0.2621 (5)	0.3496 (4)	0.31001 (14)	0.0195 (6)
C12	0.0463 (5)	0.4025 (4)	0.31992 (15)	0.0237 (7)
H12	−0.0304	0.3951	0.3565	0.028*
C13	−0.0413 (6)	0.4706 (4)	0.26501 (16)	0.0274 (8)
H13	−0.1881	0.5165	0.2576	0.033*
C14	0.1252 (5)	0.4571 (4)	0.22545 (15)	0.0248 (7)
H14	0.1135	0.4946	0.1850	0.030*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0194 (11)	0.0244 (11)	0.0235 (12)	0.0027 (9)	−0.0027 (9)	−0.0039 (9)
O2	0.0255 (12)	0.0295 (11)	0.0186 (11)	−0.0028 (10)	−0.0054 (9)	0.0042 (9)
C1	0.0176 (14)	0.0118 (12)	0.0178 (14)	−0.0041 (11)	−0.0043 (11)	0.0015 (11)
C2	0.0193 (15)	0.0099 (12)	0.0200 (15)	−0.0036 (11)	−0.0035 (11)	0.0008 (11)
C3	0.0190 (14)	0.0170 (13)	0.0229 (15)	−0.0047 (12)	−0.0074 (11)	0.0033 (12)
C4	0.0303 (18)	0.0219 (15)	0.0217 (16)	−0.0050 (13)	−0.0100 (13)	0.0099 (12)
C5	0.0370 (19)	0.0245 (15)	0.0131 (14)	−0.0084 (14)	0.0009 (13)	0.0016 (12)
C6	0.0230 (16)	0.0201 (14)	0.0221 (15)	−0.0078 (13)	0.0014 (12)	0.0004 (12)
C7	0.0208 (15)	0.0106 (11)	0.0205 (15)	−0.0046 (11)	−0.0030 (11)	−0.0005 (11)
C8	0.0172 (15)	0.0148 (12)	0.0197 (14)	−0.0006 (11)	−0.0011 (11)	−0.0028 (11)
C9	0.0149 (14)	0.0127 (12)	0.0233 (15)	−0.0041 (11)	−0.0037 (11)	−0.0002 (12)
C10	0.0151 (14)	0.0166 (13)	0.0211 (15)	−0.0026 (11)	−0.0029 (11)	−0.0033 (11)
C11	0.0256 (15)	0.0161 (13)	0.0166 (15)	0.0000 (12)	−0.0046 (12)	−0.0015 (11)
C12	0.0223 (16)	0.0281 (15)	0.0204 (16)	0.0048 (13)	−0.0033 (11)	−0.0011 (13)
C13	0.032 (2)	0.0290 (16)	0.0210 (16)	0.0024 (15)	−0.0080 (12)	0.0009 (14)
C14	0.0253 (18)	0.0261 (15)	0.0224 (17)	−0.0044 (13)	−0.0097 (12)	0.0065 (13)

O1—C1	1.220 (4)	C6—H6	0.9500
O2—C14	1.355 (4)	C7—C8	1.518 (4)
O2—C11	1.384 (4)	C8—C9	1.501 (4)
C1—C2	1.466 (4)	C8—H8A	0.9900
C1—C9	1.491 (4)	C8—H8B	0.9900
C2—C7	1.401 (4)	C9—C10	1.346 (4)
C2—C3	1.403 (4)	C10—C11	1.429 (4)
C3—C4	1.383 (5)	C10—H10	0.9500
C3—H3	0.9500	C11—C12	1.367 (4)
C4—C5	1.398 (5)	C12—C13	1.420 (4)
C4—H4	0.9500	C12—H12	0.9500
C5—C6	1.384 (4)	C13—C14	1.349 (5)
C5—H5	0.9500	C13—H13	0.9500
C6—C7	1.400 (5)	C14—H14	0.9500

C14—O2—C11	106.8 (2)	C9—C8—H8A	111.2
O1—C1—C2	127.2 (3)	C7—C8—H8A	111.2
O1—C1—C9	126.6 (3)	C9—C8—H8B	111.2
C2—C1—C9	106.1 (2)	C7—C8—H8B	111.2
C7—C2—C3	120.8 (3)	H8A—C8—H8B	109.1
C7—C2—C1	110.0 (3)	C10—C9—C1	121.1 (3)
C3—C2—C1	129.2 (3)	C10—C9—C8	129.2 (3)
C4—C3—C2	118.2 (3)	C1—C9—C8	109.6 (2)
C4—C3—H3	120.9	C9—C10—C11	126.1 (3)
C2—C3—H3	120.9	C9—C10—H10	116.9
C3—C4—C5	121.1 (3)	C11—C10—H10	116.9
C3—C4—H4	119.5	C12—C11—O2	108.9 (3)
C5—C4—H4	119.5	C12—C11—C10	135.2 (3)
C6—C5—C4	121.2 (3)	O2—C11—C10	115.9 (3)
C6—C5—H5	119.4	C11—C12—C13	106.9 (3)
C4—C5—H5	119.4	C11—C12—H12	126.6
C5—C6—C7	118.4 (3)	C13—C12—H12	126.6
C5—C6—H6	120.8	C14—C13—C12	106.4 (3)
C7—C6—H6	120.8	C14—C13—H13	126.8
C6—C7—C2	120.4 (3)	C12—C13—H13	126.8
C6—C7—C8	128.7 (3)	C13—C14—O2	111.0 (3)
C2—C7—C8	110.9 (3)	C13—C14—H14	124.5
C9—C8—C7	103.1 (2)	O2—C14—H14	124.5

O1—C1—C2—C7	−179.3 (3)	O1—C1—C9—C10	−6.6 (4)
C9—C1—C2—C7	2.9 (3)	C2—C1—C9—C10	171.3 (3)
O1—C1—C2—C3	0.2 (5)	O1—C1—C9—C8	177.2 (3)
C9—C1—C2—C3	−177.6 (3)	C2—C1—C9—C8	−5.0 (3)
C7—C2—C3—C4	−0.6 (4)	C7—C8—C9—C10	−170.9 (3)
C1—C2—C3—C4	179.9 (3)	C7—C8—C9—C1	5.0 (3)
C2—C3—C4—C5	1.3 (4)	C1—C9—C10—C11	−177.8 (3)
C3—C4—C5—C6	−1.2 (5)	C8—C9—C10—C11	−2.4 (5)
C4—C5—C6—C7	0.4 (4)	C14—O2—C11—C12	0.4 (3)
C5—C6—C7—C2	0.2 (4)	C14—O2—C11—C10	180.0 (2)
C5—C6—C7—C8	179.2 (3)	C9—C10—C11—C12	−13.2 (5)
C3—C2—C7—C6	−0.1 (4)	C9—C10—C11—O2	167.3 (3)
C1—C2—C7—C6	179.5 (2)	O2—C11—C12—C13	0.2 (3)
C3—C2—C7—C8	−179.3 (2)	C10—C11—C12—C13	−179.4 (3)
C1—C2—C7—C8	0.3 (3)	C11—C12—C13—C14	−0.6 (4)
C6—C7—C8—C9	177.6 (3)	C12—C13—C14—O2	0.9 (4)
C2—C7—C8—C9	−3.3 (3)	C11—O2—C14—C13	−0.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1ⁱ	0.95	2.56	3.414 (4)	149
C8—H8A···O1ⁱⁱ	0.99	2.37	3.343 (4)	166
C14—H14···O1ⁱⁱⁱ	0.95	2.45	3.372 (4)	164
C8—H8B···Cg1^iv	0.99	2.70	3.517 (3)	140

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1ⁱ	0.95	2.56	3.414 (4)	149
C8—H8A⋯O1ⁱⁱ	0.99	2.37	3.343 (4)	166
C14—H14⋯O1ⁱⁱⁱ	0.95	2.45	3.372 (4)	164
C8—H8B⋯Cg1^iv	0.99	2.70	3.517 (3)	140

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

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

Authors: Abdullah M Asiri; Hassan M Faidallah; Khalid A Alamry; Seik Weng Ng; Edward R T Tiekink
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2012-07-04