3-(1,3-Benzodioxol-5-yl)-3H-benzo[f]isobenzofuran-1-one

Thenmozhi, S.; SubbiahPandi, A.; Arulclement, J.; MohanaKrishnan, A.K.

doi:10.1107/S1600536810010068

organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page o894

doi:10.1107/S1600536810010068

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3-(1,3-Benzodioxol-5-yl)-3H-benzo[f]isobenzofuran-1-one

S. Thenmozhi,^a A. SubbiahPandi,^a ^* J. Arulclement ^b and A. K. MohanaKrishnan ^b

^aDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, and ^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India
^*Correspondence e-mail: as_pandian59@yahoo.com

(Received 25 February 2010; accepted 17 March 2010; online 20 March 2010)

In the title compound, C₁₉H₁₂O₄, the dioxole ring adopts a flattened envelope conformation with the methylene C at the flap [deviation = 0.104 (2) Å]. The benzene ring of the benzodioxole ring system makes a dihedral angle of 76.45 (5)° with the planar [maximum deviation = 0.016 (1) Å] 3H-benzo[f]isobenzofuran-1-one ring system. In the crystal structure, the molecules are linked into C(5) chains running along the b axis by intermolecular C—H⋯O hydrogen bonds. In addition, C—H⋯π interactions are observed.

Related literature

For the biological activity of benzofuran compounds, see: Howlett et al. (1999 ); Twyman & Allsop (1999 ); Valerga et al. (2009 ).

Experimental

Crystal data

C₁₉H₁₂O₄
M_r = 304.29
Monoclinic, P 2₁ /c
a = 7.8617 (3) Å
b = 12.0417 (4) Å
c = 15.0214 (5) Å
β = 95.848 (2)°
V = 1414.65 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.21 × 0.19 × 0.17 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.979, T_max = 0.983
19039 measured reflections
4251 independent reflections
3370 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.137
S = 1.02
4251 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C13–C18 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O1ⁱ	0.98	2.39	3.3277 (16)	159
C3—H3⋯Cg1ⁱⁱ	0.93	2.84	3.6021 (15)	140
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+2, -y+2, -z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810010068/ci5047sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810010068/ci5047Isup2.hkl

checkCIF report

Comment top

Molecules containing a benzofuran ring system have attracted considerable interest in view of their biological and pharmacological properties (Howlett et al., 1999; Twyman & Allsop, 1999). Furan compounds exhibit antibacterial and antifungal activities (Valerga et al., 2009). Against this background and in order to obtain detailed information on molecular conformation in the solid state, an X-ray crystallographic study of the title compound has been carried out and the results are presented here.

The 3H-benzo[f]isobenzofuran-1-one ring system is essentially planar, with a maximum deviation of 0.016 (1) Å for atom C12. In the 1,3-benzodioxole ring system, the dioxole ring adopts a flattened envelope conformation with the methylene C at the flap [deviation = 0.104 (2) Å]. The benzene ring of the benzodioxole ring system makes a dihedral angle of 76.45 (5)° with the 3H-benzo[f]isobenzofuran-1-one ring system.

In the crystal structure, intermolecular C—H···O hydrogen bonds (Table 1) involving atoms C12 and O1, link the molecules into chains which run parallel to the b axis and can be described by a graph set motif of C(5). In addition, the crystal packing is stabilized by C—H···π interactions involving the C13–C18 ring.

Related literature top

For the biological activity of benzofuran compounds, see: Howlett et al. (1999); Twyman & Allsop (1999); Valerga et al. (2009).

Experimental top

NaBH₄ (1.6 g, 43.75 mmol) was carefully added in small portions to a solution of keto acid (3.5 g, 10.93 mmol) in THF-EtOH (2:5) at 273 K. The reaction mixture was refluxed for 12 h and then poured into ice water (200 ml). The reaction mixture was acidified using HCl (pH = 2-3) and then stirred for 0.5 h at room temperature. The solid formed was filtered and washed with methanol to afford lactone as a colourless solid.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

3-(1,3-Benzodioxol-5-yl)-3H-benzo[f]isobenzofuran-1-one top

Crystal data top

C₁₉H₁₂O₄	F(000) = 632
M_r = 304.29	D_x = 1.429 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4251 reflections
a = 7.8617 (3) Å	θ = 2.2–30.4°
b = 12.0417 (4) Å	µ = 0.10 mm⁻¹
c = 15.0214 (5) Å	T = 293 K
β = 95.848 (2)°	Block, colourless
V = 1414.65 (9) Å³	0.21 × 0.19 × 0.17 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	4251 independent reflections
Radiation source: fine-focus sealed tube	3370 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ω scans	θ_max = 30.4°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→10
T_min = 0.979, T_max = 0.983	k = −17→16
19039 measured reflections	l = −21→13

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0727P)² + 0.2801P] where P = (F_o² + 2F_c²)/3
4251 reflections	(Δ/σ)_max = 0.002
208 parameters	Δρ_max = 0.34 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₉H₁₂O₄	V = 1414.65 (9) Å³
M_r = 304.29	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.8617 (3) Å	µ = 0.10 mm⁻¹
b = 12.0417 (4) Å	T = 293 K
c = 15.0214 (5) Å	0.21 × 0.19 × 0.17 mm
β = 95.848 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	4251 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3370 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.983	R_int = 0.038
19039 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.137	H-atom parameters constrained
S = 1.02	Δρ_max = 0.34 e Å⁻³
4251 reflections	Δρ_min = −0.22 e Å⁻³
208 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.50740 (15)	1.28238 (9)	0.19129 (8)	0.0587 (3)
O2	0.58783 (11)	1.12957 (8)	0.26946 (6)	0.0419 (2)
O3	1.20824 (14)	1.15928 (9)	0.41662 (8)	0.0588 (3)
O4	1.29651 (13)	0.98350 (9)	0.46223 (8)	0.0548 (3)
C1	0.70723 (14)	1.07497 (10)	−0.02366 (7)	0.0333 (2)
C2	0.71799 (18)	1.09700 (12)	−0.11570 (9)	0.0443 (3)
H2	0.6798	1.1648	−0.1397	0.053*
C3	0.7832 (2)	1.02046 (14)	−0.16932 (9)	0.0503 (4)
H3	0.7902	1.0364	−0.2294	0.060*
C4	0.84016 (19)	0.91727 (13)	−0.13420 (9)	0.0479 (3)
H4	0.8842	0.8652	−0.1714	0.057*
C5	0.83164 (17)	0.89258 (11)	−0.04622 (9)	0.0401 (3)
H5	0.8700	0.8239	−0.0241	0.048*
C6	0.76513 (14)	0.97022 (9)	0.01198 (7)	0.0307 (2)
C7	0.75593 (14)	0.94554 (9)	0.10366 (7)	0.0313 (2)
H7	0.7938	0.8775	0.1274	0.038*
C8	0.69034 (13)	1.02365 (9)	0.15634 (7)	0.0289 (2)
C9	0.63280 (14)	1.12596 (9)	0.12091 (8)	0.0324 (2)
C10	0.64042 (16)	1.15336 (10)	0.03305 (8)	0.0369 (3)
H10	0.6023	1.2222	0.0112	0.044*
C11	0.56804 (15)	1.19097 (11)	0.19281 (9)	0.0396 (3)
C12	0.66602 (15)	1.02200 (10)	0.25451 (7)	0.0329 (2)
H12	0.5871	0.9622	0.2667	0.039*
C13	0.83094 (15)	1.00982 (10)	0.31446 (7)	0.0310 (2)
C14	0.88263 (17)	0.90475 (10)	0.34263 (9)	0.0389 (3)
H14	0.8110	0.8446	0.3280	0.047*
C15	1.04087 (17)	0.88686 (11)	0.39288 (9)	0.0420 (3)
H15	1.0765	0.8161	0.4114	0.050*
C16	1.13967 (16)	0.97803 (11)	0.41324 (8)	0.0364 (3)
C17	1.08753 (16)	1.08282 (10)	0.38590 (8)	0.0355 (2)
C18	0.93465 (15)	1.10207 (10)	0.33622 (8)	0.0351 (2)
H18	0.9013	1.1732	0.3178	0.042*
C19	1.34790 (18)	1.09710 (13)	0.45929 (10)	0.0497 (3)
H19A	1.3783	1.1248	0.5195	0.060*
H19B	1.4468	1.1041	0.4260	0.060*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0624 (7)	0.0454 (6)	0.0653 (7)	0.0244 (5)	−0.0085 (5)	−0.0180 (5)
O2	0.0383 (5)	0.0475 (5)	0.0398 (4)	0.0108 (4)	0.0030 (4)	−0.0106 (4)
O3	0.0477 (6)	0.0393 (5)	0.0841 (8)	−0.0062 (4)	−0.0198 (5)	−0.0088 (5)
O4	0.0438 (5)	0.0521 (6)	0.0637 (7)	0.0030 (4)	−0.0172 (5)	0.0006 (5)
C1	0.0314 (5)	0.0338 (6)	0.0336 (5)	−0.0029 (4)	−0.0020 (4)	0.0019 (4)
C2	0.0467 (7)	0.0483 (7)	0.0367 (6)	−0.0045 (6)	−0.0013 (5)	0.0095 (5)
C3	0.0534 (8)	0.0644 (9)	0.0342 (6)	−0.0127 (7)	0.0097 (5)	0.0010 (6)
C4	0.0511 (8)	0.0527 (8)	0.0424 (7)	−0.0085 (6)	0.0165 (6)	−0.0114 (6)
C5	0.0432 (6)	0.0367 (6)	0.0415 (6)	−0.0020 (5)	0.0094 (5)	−0.0059 (5)
C6	0.0292 (5)	0.0291 (5)	0.0335 (5)	−0.0028 (4)	0.0014 (4)	−0.0027 (4)
C7	0.0343 (5)	0.0248 (5)	0.0342 (5)	0.0013 (4)	0.0011 (4)	−0.0002 (4)
C8	0.0271 (5)	0.0266 (5)	0.0322 (5)	−0.0010 (4)	−0.0010 (4)	−0.0023 (4)
C9	0.0306 (5)	0.0267 (5)	0.0385 (5)	0.0038 (4)	−0.0037 (4)	−0.0043 (4)
C10	0.0391 (6)	0.0283 (5)	0.0412 (6)	0.0044 (4)	−0.0056 (5)	0.0026 (4)
C11	0.0333 (6)	0.0383 (6)	0.0453 (6)	0.0072 (5)	−0.0056 (5)	−0.0111 (5)
C12	0.0319 (5)	0.0336 (6)	0.0331 (5)	0.0005 (4)	0.0026 (4)	−0.0039 (4)
C13	0.0328 (5)	0.0335 (5)	0.0270 (5)	−0.0011 (4)	0.0037 (4)	−0.0009 (4)
C14	0.0402 (6)	0.0319 (6)	0.0440 (6)	−0.0052 (5)	0.0016 (5)	0.0033 (5)
C15	0.0453 (7)	0.0334 (6)	0.0463 (7)	0.0007 (5)	−0.0004 (5)	0.0083 (5)
C16	0.0364 (6)	0.0401 (6)	0.0320 (5)	0.0031 (5)	0.0000 (4)	0.0004 (4)
C17	0.0372 (6)	0.0325 (6)	0.0363 (5)	−0.0029 (4)	0.0010 (4)	−0.0061 (4)
C18	0.0385 (6)	0.0290 (5)	0.0373 (5)	0.0011 (4)	0.0005 (4)	−0.0013 (4)
C19	0.0391 (7)	0.0562 (9)	0.0515 (8)	−0.0040 (6)	−0.0063 (6)	−0.0052 (6)

Geometric parameters (Å, º) top

O1—C11	1.1988 (15)	C7—H7	0.93
O2—C11	1.3639 (17)	C8—C9	1.3988 (15)
O2—C12	1.4610 (14)	C8—C12	1.5063 (15)
O3—C17	1.3682 (15)	C9—C10	1.3675 (17)
O3—C19	1.4260 (18)	C9—C11	1.4665 (16)
O4—C16	1.3716 (15)	C10—H10	0.93
O4—C19	1.4283 (18)	C12—C13	1.5085 (16)
C1—C10	1.4085 (17)	C12—H12	0.98
C1—C2	1.4188 (17)	C13—C14	1.3820 (17)
C1—C6	1.4266 (16)	C13—C18	1.3969 (16)
C2—C3	1.358 (2)	C14—C15	1.4044 (18)
C2—H2	0.93	C14—H14	0.93
C3—C4	1.405 (2)	C15—C16	1.3615 (18)
C3—H3	0.93	C15—H15	0.93
C4—C5	1.3628 (19)	C16—C17	1.3765 (17)
C4—H4	0.93	C17—C18	1.3684 (17)
C5—C6	1.4160 (16)	C18—H18	0.93
C5—H5	0.93	C19—H19A	0.97
C6—C7	1.4178 (15)	C19—H19B	0.97
C7—C8	1.3638 (15)

C11—O2—C12	111.37 (9)	O1—C11—O2	121.65 (12)
C17—O3—C19	105.91 (11)	O1—C11—C9	130.04 (13)
C16—O4—C19	105.73 (10)	O2—C11—C9	108.31 (10)
C10—C1—C2	121.80 (11)	O2—C12—C8	103.66 (9)
C10—C1—C6	119.34 (10)	O2—C12—C13	110.11 (9)
C2—C1—C6	118.86 (11)	C8—C12—C13	113.49 (9)
C3—C2—C1	120.96 (13)	O2—C12—H12	109.8
C3—C2—H2	119.5	C8—C12—H12	109.8
C1—C2—H2	119.5	C13—C12—H12	109.8
C2—C3—C4	120.17 (12)	C14—C13—C18	120.66 (11)
C2—C3—H3	119.9	C14—C13—C12	118.67 (10)
C4—C3—H3	119.9	C18—C13—C12	120.54 (10)
C5—C4—C3	120.77 (13)	C13—C14—C15	121.45 (12)
C5—C4—H4	119.6	C13—C14—H14	119.3
C3—C4—H4	119.6	C15—C14—H14	119.3
C4—C5—C6	120.83 (13)	C16—C15—C14	116.80 (11)
C4—C5—H5	119.6	C16—C15—H15	121.6
C6—C5—H5	119.6	C14—C15—H15	121.6
C7—C6—C5	121.33 (11)	C15—C16—O4	128.34 (12)
C7—C6—C1	120.26 (10)	C15—C16—C17	121.77 (11)
C5—C6—C1	118.41 (11)	O4—C16—C17	109.88 (11)
C8—C7—C6	118.60 (10)	O3—C17—C18	127.62 (12)
C8—C7—H7	120.7	O3—C17—C16	109.94 (11)
C6—C7—H7	120.7	C18—C17—C16	122.43 (11)
C7—C8—C9	120.89 (10)	C17—C18—C13	116.89 (11)
C7—C8—C12	130.70 (10)	C17—C18—H18	121.6
C9—C8—C12	108.41 (9)	C13—C18—H18	121.6
C10—C9—C8	122.37 (11)	O3—C19—O4	108.03 (11)
C10—C9—C11	129.39 (11)	O3—C19—H19A	110.1
C8—C9—C11	108.24 (10)	O4—C19—H19A	110.1
C9—C10—C1	118.54 (11)	O3—C19—H19B	110.1
C9—C10—H10	120.7	O4—C19—H19B	110.1
C1—C10—H10	120.7	H19A—C19—H19B	108.4

C10—C1—C2—C3	179.83 (13)	C11—O2—C12—C8	−0.87 (12)
C6—C1—C2—C3	−0.45 (19)	C11—O2—C12—C13	120.86 (11)
C1—C2—C3—C4	0.5 (2)	C7—C8—C12—O2	−179.21 (11)
C2—C3—C4—C5	−0.3 (2)	C9—C8—C12—O2	1.19 (12)
C3—C4—C5—C6	0.0 (2)	C7—C8—C12—C13	61.35 (16)
C4—C5—C6—C7	−179.88 (12)	C9—C8—C12—C13	−118.25 (11)
C4—C5—C6—C1	−0.01 (18)	O2—C12—C13—C14	150.18 (11)
C10—C1—C6—C7	−0.20 (16)	C8—C12—C13—C14	−94.13 (13)
C2—C1—C6—C7	−179.92 (11)	O2—C12—C13—C18	−33.93 (14)
C10—C1—C6—C5	179.93 (11)	C8—C12—C13—C18	81.76 (13)
C2—C1—C6—C5	0.21 (17)	C18—C13—C14—C15	−0.74 (19)
C5—C6—C7—C8	−179.90 (11)	C12—C13—C14—C15	175.14 (11)
C1—C6—C7—C8	0.23 (16)	C13—C14—C15—C16	0.7 (2)
C6—C7—C8—C9	0.16 (16)	C14—C15—C16—O4	178.80 (13)
C6—C7—C8—C12	−179.39 (11)	C14—C15—C16—C17	−0.1 (2)
C7—C8—C9—C10	−0.61 (17)	C19—O4—C16—C15	176.89 (14)
C12—C8—C9—C10	179.03 (11)	C19—O4—C16—C17	−4.11 (15)
C7—C8—C9—C11	179.26 (10)	C19—O3—C17—C18	−176.17 (13)
C12—C8—C9—C11	−1.10 (13)	C19—O3—C17—C16	4.60 (15)
C8—C9—C10—C1	0.63 (18)	C15—C16—C17—O3	178.77 (12)
C11—C9—C10—C1	−179.21 (11)	O4—C16—C17—O3	−0.31 (15)
C2—C1—C10—C9	179.49 (12)	C15—C16—C17—C18	−0.5 (2)
C6—C1—C10—C9	−0.22 (17)	O4—C16—C17—C18	−179.59 (12)
C12—O2—C11—O1	−179.35 (12)	O3—C17—C18—C13	−178.66 (12)
C12—O2—C11—C9	0.24 (13)	C16—C17—C18—C13	0.49 (18)
C10—C9—C11—O1	0.0 (2)	C14—C13—C18—C17	0.13 (17)
C8—C9—C11—O1	−179.90 (14)	C12—C13—C18—C17	−175.68 (10)
C10—C9—C11—O2	−179.59 (12)	C17—O3—C19—O4	−7.07 (15)
C8—C9—C11—O2	0.56 (13)	C16—O4—C19—O3	6.88 (15)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C13–C18 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1ⁱ	0.98	2.39	3.3277 (16)	159
C3—H3···Cg1ⁱⁱ	0.93	2.84	3.6021 (15)	140

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₂O₄
M_r	304.29
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.8617 (3), 12.0417 (4), 15.0214 (5)
β (°)	95.848 (2)
V (Å³)	1414.65 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.21 × 0.19 × 0.17

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.979, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	19039, 4251, 3370
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.711

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.137, 1.02
No. of reflections	4251
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.22

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C13–C18 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1ⁱ	0.98	2.39	3.3277 (16)	159
C3—H3···Cg1ⁱⁱ	0.93	2.84	3.6021 (15)	140

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

Acknowledgements

ST and ASP thank Dr Babu Varghese, SAIF, IIT-Madras, Chennai, India, for the data collection.

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Howlett, D. R., Perry, A. E., Godfrey, F., Swatton, J. E., Jennings, K. H., Spitzfaden, C., Wadsworth, H., Wood, S. J. & Markwell, R. E. (1999). Biochem. J. 340, 283–289. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Gottingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Twyman, L. J. & Allsop, D. (1999). Tetrahedron Lett. 40, 9383–9384. Web of Science CrossRef CAS Google Scholar
Valerga, P., Puerta, M. C., Rodríguez Negrín, Z., Castañedo Cancio, N. & Palma Lovillo, M. (2009). Acta Cryst. E65, o1979. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 66| Part 4| April 2010| Page o894

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