(2E)-2-[(2H-1,3-Benzodioxol-5-yl)methyl-idene]-2,3-dihydro-1H-inden-1-one.

In the title compound, C(17)H(12)O(3), each of the five-membered rings in the inden-1-one and 1,3-benzodioxole residues is almost planar (r.m.s. deviations = 0.041 and 0.033 Å, respectively). A small twist about the single bond linking the two residues is evident [the C-C-C-C torsion angle = 8.7 (4)°]. Supra-molecular zigzag layers propagating in the ac plane are formed in the crystal via C-H⋯O inter-actions. The layers are linked via π-π inter-actions between the five- and six-membered rings of 1,3-benzodioxole residues [centroid-centroid distance = 3.4977 (14) Å].

Related literature

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

Experimental

Crystal data

C17H12O3

M = 264.27

Orthorhombic,

a = 12.6102 (12) Å

b = 7.3497 (10) Å

c = 26.569 (4) Å

V = 2462.5 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.35 × 0.10 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.967, T max = 0.995

6424 measured reflections

2820 independent reflections

1697 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.136

S = 0.98

2820 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.26 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/S1600536812009464/hb6667sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812009464/hb6667Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812009464/hb6667Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H12O3	F(000) = 1104
Mr = 264.27	Dx = 1.426 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 930 reflections
a = 12.6102 (12) Å	θ = 2.8–27.5°
b = 7.3497 (10) Å	µ = 0.10 mm−1
c = 26.569 (4) Å	T = 100 K
V = 2462.5 (5) Å3	Prism, light-yellow
Z = 8	0.35 × 0.10 × 0.05 mm

Agilent SuperNova Dual diffractometer with an Atlas detector	2820 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1697 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.057
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 3.2°
ω scan	h = −16→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −9→6
Tmin = 0.967, Tmax = 0.995	l = −34→22
6424 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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.0502P)2] where P = (Fo2 + 2Fc2)/3
2820 reflections	(Δ/σ)max = 0.001
181 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.92949 (12)	0.5693 (2)	0.65488 (6)	0.0275 (4)
O2	0.61242 (12)	0.2489 (2)	0.41852 (5)	0.0283 (4)
O3	0.75515 (12)	0.1445 (2)	0.37080 (6)	0.0283 (4)
C1	0.83441 (19)	0.5422 (3)	0.64704 (8)	0.0212 (5)
C2	0.74657 (18)	0.5690 (3)	0.68310 (8)	0.0197 (5)
C3	0.75035 (19)	0.6274 (3)	0.73287 (8)	0.0231 (5)
H3	0.8154	0.6647	0.7476	0.028*
C4	0.65715 (19)	0.6298 (3)	0.76036 (8)	0.0267 (6)
H4	0.6578	0.6709	0.7943	0.032*
C5	0.5625 (2)	0.5723 (3)	0.73861 (9)	0.0291 (6)
H5	0.4996	0.5711	0.7583	0.035*
C6	0.55825 (19)	0.5165 (3)	0.68870 (8)	0.0263 (6)
H6	0.4931	0.4781	0.6742	0.032*
C7	0.65094 (18)	0.5179 (3)	0.66035 (8)	0.0210 (5)
C8	0.66690 (17)	0.4682 (3)	0.60554 (8)	0.0200 (5)
H8A	0.6391	0.3449	0.5983	0.024*
H8B	0.6314	0.5569	0.5831	0.024*
C9	0.78635 (18)	0.4750 (3)	0.59906 (8)	0.0199 (5)
C10	0.84909 (18)	0.4281 (3)	0.56046 (8)	0.0207 (5)
H10	0.9227	0.4445	0.5665	0.025*
C11	0.82372 (18)	0.3562 (3)	0.51066 (8)	0.0194 (5)
C12	0.90839 (19)	0.2975 (3)	0.48054 (8)	0.0254 (5)
H12	0.9785	0.3069	0.4934	0.030*
C13	0.89343 (19)	0.2255 (3)	0.43228 (8)	0.0266 (5)
H13	0.9514	0.1870	0.4121	0.032*
C14	0.79071 (19)	0.2135 (3)	0.41575 (8)	0.0221 (5)
C15	0.70630 (17)	0.2729 (3)	0.44464 (8)	0.0197 (5)
C16	0.71892 (18)	0.3447 (3)	0.49167 (8)	0.0210 (5)
H16	0.6599	0.3851	0.5109	0.025*
C17	0.64264 (19)	0.1752 (4)	0.37035 (8)	0.0296 (6)
H17A	0.6048	0.0593	0.3642	0.036*
H17B	0.6239	0.2616	0.3432	0.036*

	U11	U22	U33	U12	U13	U23
O1	0.0173 (9)	0.0395 (10)	0.0256 (9)	−0.0010 (7)	−0.0025 (7)	−0.0025 (8)
O2	0.0210 (9)	0.0432 (11)	0.0206 (8)	−0.0023 (8)	−0.0017 (7)	−0.0073 (7)
O3	0.0210 (9)	0.0422 (10)	0.0217 (8)	−0.0029 (8)	0.0018 (7)	−0.0092 (8)
C1	0.0204 (13)	0.0226 (12)	0.0206 (11)	0.0005 (10)	−0.0012 (10)	0.0010 (9)
C2	0.0202 (12)	0.0193 (11)	0.0196 (11)	0.0004 (10)	0.0017 (10)	0.0007 (9)
C3	0.0221 (13)	0.0265 (12)	0.0207 (11)	−0.0010 (10)	−0.0025 (10)	0.0012 (10)
C4	0.0299 (14)	0.0312 (13)	0.0189 (11)	0.0050 (11)	0.0016 (11)	−0.0016 (10)
C5	0.0233 (14)	0.0379 (15)	0.0261 (12)	0.0057 (11)	0.0056 (11)	0.0000 (11)
C6	0.0205 (13)	0.0352 (14)	0.0231 (12)	0.0021 (11)	0.0006 (10)	0.0018 (10)
C7	0.0195 (12)	0.0203 (11)	0.0230 (11)	0.0021 (10)	0.0002 (10)	0.0009 (9)
C8	0.0183 (12)	0.0218 (11)	0.0200 (11)	−0.0009 (10)	0.0008 (10)	−0.0004 (9)
C9	0.0186 (12)	0.0214 (11)	0.0199 (11)	0.0002 (10)	−0.0001 (10)	0.0015 (9)
C10	0.0156 (12)	0.0231 (12)	0.0234 (11)	−0.0021 (9)	−0.0010 (10)	0.0030 (10)
C11	0.0195 (12)	0.0195 (11)	0.0191 (10)	−0.0012 (10)	0.0013 (10)	0.0026 (9)
C12	0.0177 (13)	0.0333 (13)	0.0251 (11)	−0.0028 (10)	0.0009 (10)	0.0006 (10)
C13	0.0183 (13)	0.0353 (13)	0.0260 (12)	−0.0006 (11)	0.0052 (11)	−0.0019 (10)
C14	0.0231 (13)	0.0257 (12)	0.0175 (10)	−0.0013 (10)	0.0038 (10)	−0.0005 (10)
C15	0.0169 (12)	0.0209 (11)	0.0213 (11)	−0.0027 (9)	−0.0028 (10)	0.0026 (9)
C16	0.0183 (12)	0.0252 (12)	0.0196 (11)	−0.0017 (10)	0.0029 (10)	0.0024 (10)
C17	0.0248 (14)	0.0421 (16)	0.0218 (11)	0.0053 (11)	−0.0002 (11)	−0.0046 (11)

O1—C1	1.233 (3)	C8—C9	1.517 (3)
O2—C15	1.384 (3)	C8—H8A	0.9900
O2—C17	1.441 (3)	C8—H8B	0.9900
O3—C14	1.373 (3)	C9—C10	1.340 (3)
O3—C17	1.437 (3)	C10—C11	1.460 (3)
C1—C2	1.478 (3)	C10—H10	0.9500
C1—C9	1.496 (3)	C11—C12	1.402 (3)
C2—C3	1.391 (3)	C11—C16	1.417 (3)
C2—C7	1.400 (3)	C12—C13	1.400 (3)
C3—C4	1.384 (3)	C12—H12	0.9500
C3—H3	0.9500	C13—C14	1.371 (3)
C4—C5	1.392 (3)	C13—H13	0.9500
C4—H4	0.9500	C14—C15	1.383 (3)
C5—C6	1.389 (3)	C15—C16	1.366 (3)
C5—H5	0.9500	C16—H16	0.9500
C6—C7	1.391 (3)	C17—H17A	0.9900
C6—H6	0.9500	C17—H17B	0.9900
C7—C8	1.515 (3)
C15—O2—C17	105.49 (17)	C10—C9—C8	131.7 (2)
C14—O3—C17	105.78 (16)	C1—C9—C8	108.44 (18)
O1—C1—C2	126.7 (2)	C9—C10—C11	131.1 (2)
O1—C1—C9	126.3 (2)	C9—C10—H10	114.5
C2—C1—C9	107.04 (19)	C11—C10—H10	114.5
C3—C2—C7	121.5 (2)	C12—C11—C16	119.2 (2)
C3—C2—C1	129.2 (2)	C12—C11—C10	117.5 (2)
C7—C2—C1	109.26 (19)	C16—C11—C10	123.3 (2)
C4—C3—C2	118.5 (2)	C13—C12—C11	122.4 (2)
C4—C3—H3	120.8	C13—C12—H12	118.8
C2—C3—H3	120.8	C11—C12—H12	118.8
C3—C4—C5	120.3 (2)	C14—C13—C12	116.4 (2)
C3—C4—H4	119.8	C14—C13—H13	121.8
C5—C4—H4	119.8	C12—C13—H13	121.8
C6—C5—C4	121.3 (2)	C13—C14—O3	127.7 (2)
C6—C5—H5	119.4	C13—C14—C15	121.9 (2)
C4—C5—H5	119.4	O3—C14—C15	110.4 (2)
C7—C6—C5	118.9 (2)	C16—C15—C14	122.7 (2)
C7—C6—H6	120.6	C16—C15—O2	127.4 (2)
C5—C6—H6	120.6	C14—C15—O2	109.86 (19)
C6—C7—C2	119.5 (2)	C15—C16—C11	117.2 (2)
C6—C7—C8	129.1 (2)	C15—C16—H16	121.4
C2—C7—C8	111.42 (19)	C11—C16—H16	121.4
C9—C8—C7	103.49 (17)	O3—C17—O2	108.22 (17)
C9—C8—H8A	111.1	O3—C17—H17A	110.1
C7—C8—H8A	111.1	O2—C17—H17A	110.1
C9—C8—H8B	111.1	O3—C17—H17B	110.1
C7—C8—H8B	111.1	O2—C17—H17B	110.1
H8A—C8—H8B	109.0	H17A—C17—H17B	108.4
C10—C9—C1	119.9 (2)
O1—C1—C2—C3	−0.8 (4)	C1—C9—C10—C11	178.6 (2)
C9—C1—C2—C3	179.0 (2)	C8—C9—C10—C11	1.0 (4)
O1—C1—C2—C7	−178.2 (2)	C9—C10—C11—C12	−171.8 (2)
C9—C1—C2—C7	1.6 (2)	C9—C10—C11—C16	8.7 (4)
C7—C2—C3—C4	1.6 (3)	C16—C11—C12—C13	−0.7 (3)
C1—C2—C3—C4	−175.5 (2)	C10—C11—C12—C13	179.7 (2)
C2—C3—C4—C5	1.0 (3)	C11—C12—C13—C14	−0.5 (3)
C3—C4—C5—C6	−2.0 (4)	C12—C13—C14—O3	−178.3 (2)
C4—C5—C6—C7	0.3 (3)	C12—C13—C14—C15	1.4 (3)
C5—C6—C7—C2	2.2 (3)	C17—O3—C14—C13	−175.9 (2)
C5—C6—C7—C8	−178.5 (2)	C17—O3—C14—C15	4.3 (2)
C3—C2—C7—C6	−3.2 (3)	C13—C14—C15—C16	−1.1 (4)
C1—C2—C7—C6	174.43 (19)	O3—C14—C15—C16	178.7 (2)
C3—C2—C7—C8	177.4 (2)	C13—C14—C15—O2	178.5 (2)
C1—C2—C7—C8	−5.0 (2)	O3—C14—C15—O2	−1.7 (3)
C6—C7—C8—C9	−173.2 (2)	C17—O2—C15—C16	177.9 (2)
C2—C7—C8—C9	6.1 (2)	C17—O2—C15—C14	−1.7 (2)
O1—C1—C9—C10	3.9 (3)	C14—C15—C16—C11	−0.2 (3)
C2—C1—C9—C10	−175.9 (2)	O2—C15—C16—C11	−179.78 (19)
O1—C1—C9—C8	−177.9 (2)	C12—C11—C16—C15	1.1 (3)
C2—C1—C9—C8	2.3 (2)	C10—C11—C16—C15	−179.4 (2)
C7—C8—C9—C10	172.9 (2)	C14—O3—C17—O2	−5.3 (2)
C7—C8—C9—C1	−4.9 (2)	C15—O2—C17—O3	4.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1i	0.95	2.47	3.290 (3)	144
C17—H17A···O1ii	0.99	2.46	3.302 (3)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1i	0.95	2.47	3.290 (3)	144
C17—H17A⋯O1ii	0.99	2.46	3.302 (3)	143

Symmetry codes: (i) ; (ii) .