3-(Anthracen-9-yl)-3H-isobenzofuran-1-one

Palani, K.; Amaladass, P.; Mohanakrishnan, A.K.; Ponnuswamy, M.N.

doi:10.1107/S1600536805039553

3-(Anthracen-9-yl)-3H-isobenzofuran-1-one

K. Palani, P. Amaladass, A. K. Mohanakrishnan and M. N. Ponnuswamy

In the title compound, C₂₂H₁₄O₂, the dihedral angle between the planes of the anthracene and the benzofuranone ring systems is 70.74 (4)°. The crystal packing is stabilized by C—H

π interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805039553/ci6718sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805039553/ci6718Isup2.hkl Contains datablock I

CCDC reference: 296539

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.049
wR factor = 0.125
Data-to-parameter ratio = 11.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT410_ALERT_2_C Short Intra H...H Contact  H12    ..  H15     ..       1.91 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12    ..  CG2     ..       2.94 Ang.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           30.08
           From the CIF: _reflns_number_total               2462
           Count of symmetry unique reflns         2495
           Completeness (_total/calc)             98.68%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

The design of fluorescent chemosensors is an aspect in the field of supramolecular chemistry (de Silva et al., 1997). Many fluorescent sensors containing the anthracene ring system have been designed and investigated (Wang et al., 2002). The fluorescence intensity of compounds with anthracene chromophores can be effectively modulated by introducing different substituents (Luigi & Antonio, 1995). In view of this, the crystal structure of the title compound (I) was determined to establish the conformation of the molecule.

A ORTEP-3 (Farrugia, 1997) plot of the molecule is shown in Fig.1. The bond lengths and bond angles in the anthracene ring system are comparable to those reported for 9-oxo-10-diphenylphosphinoylanthracene (Liu & Song, 2005). The anthracene ring system is approximately planar, with a maximum deviation of 0.138 (2) Å for C3. The dihedral angle between the planes of the anthracene and the isobenzofuranone ring systems is 70.74 (4)°.

An intramolecular C2—H2···O1 hydrogen bond leads to the formation of an S(5) ring motif (Bernstein, et al., 1995). The crystal structure is stabilized by C—H···π interactions (Table 2) involving the C1C6 benzene ring (centroid Cg1) [Fig. 2].

Experimental top

A dry 50 ml round bottom flask was charged with ethyl-2-iodobenzoate (7.24 mmol) in dry THF (10 ml) and cooled to 253 K, isopropyl magnesium bromide (7.24 mmol) was slowly added. After 1 h, when the exchange was completed, 9-anthracene carboxaldehyde (7.24 mmol) was added as a solution in THF (5 ml). The reaction mixture was allowed to warm at room temperature over 30 min. The reaction mixture was poured into NH₄Cl solution (20 ml) and extracted with ethyl acetate (50 ml). The crude residue was recrystallized from boiling hexane to afford good quality crystals.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids. The dashed line indicates a hydrogen bond.
	Fig. 2. The crystal packing of (I), viewed down the a axis. Dashed lines indicate C—H···π interactions.

3-(Anthracen-9-yl)-3H-isobenzofuran-1-one top

Crystal data top

C₂₂H₁₄O₂	F(000) = 648
M_r = 310.33	D_x = 1.377 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 9.961 (4) Å	θ = 10–15°
b = 10.677 (5) Å	µ = 0.09 mm⁻¹
c = 14.073 (5) Å	T = 293 K
V = 1496.7 (11) Å³	Prism, yellow
Z = 4	0.34 × 0.20 × 0.18 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.000
Radiation source: fine-focus sealed tube	θ_max = 30.1°, θ_min = 2.4°
Graphite monochromator	h = 0→13
ω scans	k = 0→15
2462 measured reflections	l = 0→19
2462 independent reflections	3 standard reflections every 60 min
1469 reflections with I > 2σ(I)	intensity decay: none

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0607P)² + 0.0612P] where P = (F_o² + 2F_c²)/3
2462 reflections	(Δ/σ)_max = 0.001
217 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₂H₁₄O₂	V = 1496.7 (11) Å³
M_r = 310.33	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.961 (4) Å	µ = 0.09 mm⁻¹
b = 10.677 (5) Å	T = 293 K
c = 14.073 (5) Å	0.34 × 0.20 × 0.18 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.000
2462 measured reflections	3 standard reflections every 60 min
2462 independent reflections	intensity decay: none
1469 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 1.06	Δρ_max = 0.23 e Å⁻³
2462 reflections	Δρ_min = −0.20 e Å⁻³
217 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
C13	0.8926 (2)	0.7573 (2)	0.15880 (17)	0.0447 (6)
C1	1.1060 (3)	0.8666 (2)	0.13409 (16)	0.0456 (6)
O1	1.19636 (19)	0.72995 (17)	0.30922 (13)	0.0588 (5)
C15	1.0898 (2)	0.6807 (2)	0.24936 (17)	0.0475 (6)
H15	1.0173	0.6523	0.2913	0.057*
C14	1.0303 (2)	0.7727 (2)	0.18028 (16)	0.0441 (5)
C8	0.8276 (2)	0.8420 (3)	0.09581 (17)	0.0485 (6)
C6	1.0379 (3)	0.9527 (2)	0.07386 (17)	0.0481 (6)
C16	1.1515 (2)	0.5666 (2)	0.20494 (18)	0.0466 (6)
C17	1.0996 (3)	0.4829 (2)	0.14111 (19)	0.0544 (7)
H17	1.0137	0.4929	0.1164	0.065*
C7	0.9008 (3)	0.9393 (3)	0.05757 (17)	0.0515 (6)
H7	0.8571	0.9979	0.0197	0.062*
C21	1.2796 (2)	0.5516 (2)	0.24047 (18)	0.0502 (6)
C2	1.2494 (3)	0.8797 (3)	0.1402 (2)	0.0549 (7)
H2	1.2977	0.8245	0.1781	0.066*
C5	1.1128 (3)	1.0479 (2)	0.02647 (19)	0.0577 (7)
H5	1.0680	1.1060	−0.0112	0.069*
C12	0.8121 (3)	0.6581 (3)	0.1957 (2)	0.0560 (7)
H12	0.8503	0.6006	0.2373	0.067*
C11	0.6812 (3)	0.6458 (3)	0.1713 (2)	0.0646 (8)
H11	0.6320	0.5794	0.1961	0.078*
C9	0.6891 (3)	0.8252 (3)	0.07367 (19)	0.0614 (7)
H9	0.6470	0.8816	0.0331	0.074*
C10	0.6184 (3)	0.7297 (3)	0.1103 (2)	0.0658 (8)
H10	0.5282	0.7198	0.0951	0.079*
C18	1.1794 (3)	0.3830 (3)	0.1148 (2)	0.0627 (8)
H18	1.1460	0.3244	0.0720	0.075*
C20	1.3596 (3)	0.4520 (3)	0.2135 (2)	0.0608 (7)
H20	1.4460	0.4427	0.2376	0.073*
C3	1.3152 (3)	0.9697 (3)	0.0924 (2)	0.0618 (7)
H3	1.4081	0.9750	0.0976	0.074*
C4	1.2470 (3)	1.0554 (3)	0.0352 (2)	0.0637 (8)
H4	1.2943	1.1175	0.0031	0.076*
C19	1.3079 (3)	0.3679 (3)	0.1505 (2)	0.0655 (8)
H19	1.3595	0.2999	0.1313	0.079*
C22	1.3058 (3)	0.6525 (3)	0.3078 (2)	0.0592 (7)
O2	1.4020 (2)	0.6738 (2)	0.35692 (17)	0.0832 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C13	0.0429 (13)	0.0465 (13)	0.0447 (11)	0.0043 (11)	0.0028 (11)	−0.0068 (11)
C1	0.0511 (14)	0.0450 (12)	0.0406 (12)	0.0031 (11)	0.0012 (11)	−0.0051 (11)
O1	0.0626 (11)	0.0613 (10)	0.0526 (9)	−0.0014 (10)	−0.0122 (9)	−0.0018 (9)
C15	0.0465 (12)	0.0500 (13)	0.0460 (13)	−0.0005 (12)	−0.0042 (11)	0.0033 (11)
C14	0.0452 (12)	0.0439 (12)	0.0431 (12)	0.0048 (11)	0.0034 (10)	−0.0030 (11)
C8	0.0468 (13)	0.0568 (15)	0.0420 (12)	0.0092 (13)	−0.0004 (11)	−0.0078 (12)
C6	0.0565 (15)	0.0463 (14)	0.0414 (12)	0.0035 (12)	0.0031 (12)	−0.0044 (12)
C16	0.0465 (13)	0.0462 (13)	0.0470 (13)	−0.0010 (11)	0.0017 (10)	0.0118 (11)
C17	0.0563 (16)	0.0499 (14)	0.0569 (15)	−0.0041 (13)	−0.0022 (13)	0.0041 (13)
C7	0.0595 (15)	0.0524 (14)	0.0424 (12)	0.0142 (13)	−0.0039 (11)	0.0014 (12)
C21	0.0456 (13)	0.0527 (14)	0.0525 (13)	−0.0038 (12)	−0.0001 (11)	0.0159 (12)
C2	0.0479 (14)	0.0569 (16)	0.0598 (15)	0.0014 (13)	0.0023 (12)	0.0035 (14)
C5	0.0757 (19)	0.0461 (14)	0.0513 (14)	0.0025 (15)	0.0036 (14)	0.0034 (12)
C12	0.0513 (14)	0.0555 (15)	0.0611 (16)	−0.0058 (13)	0.0037 (14)	−0.0011 (14)
C11	0.0523 (16)	0.0668 (17)	0.0748 (19)	−0.0114 (15)	0.0028 (15)	−0.0122 (16)
C9	0.0533 (15)	0.079 (2)	0.0516 (14)	0.0113 (16)	−0.0090 (14)	−0.0144 (15)
C10	0.0464 (15)	0.083 (2)	0.0682 (17)	−0.0042 (16)	−0.0047 (14)	−0.0254 (18)
C18	0.076 (2)	0.0468 (15)	0.0657 (17)	−0.0034 (15)	0.0112 (16)	0.0013 (13)
C20	0.0479 (13)	0.0646 (17)	0.0699 (17)	0.0079 (14)	0.0099 (13)	0.0260 (16)
C3	0.0522 (15)	0.0640 (19)	0.0693 (17)	−0.0082 (15)	0.0056 (15)	−0.0014 (16)
C4	0.0738 (19)	0.0526 (15)	0.0647 (16)	−0.0138 (15)	0.0133 (15)	0.0027 (15)
C19	0.0689 (19)	0.0543 (16)	0.0734 (18)	0.0098 (15)	0.0247 (17)	0.0126 (15)
C22	0.0530 (15)	0.0670 (17)	0.0576 (15)	−0.0013 (15)	−0.0076 (13)	0.0160 (14)
O2	0.0685 (13)	0.0930 (16)	0.0881 (15)	−0.0104 (13)	−0.0305 (13)	0.0055 (13)

Geometric parameters (Å, º) top

C13—C14	1.414 (3)	C21—C22	1.459 (4)
C13—C8	1.422 (3)	C2—C3	1.344 (4)
C13—C12	1.427 (4)	C2—H2	0.93
C1—C14	1.412 (3)	C5—C4	1.344 (4)
C1—C6	1.422 (3)	C5—H5	0.93
C1—C2	1.438 (3)	C12—C11	1.354 (4)
O1—C22	1.368 (3)	C12—H12	0.93
O1—C15	1.454 (3)	C11—C10	1.390 (4)
C15—C16	1.501 (4)	C11—H11	0.93
C15—C14	1.504 (3)	C9—C10	1.342 (4)
C15—H15	0.98	C9—H9	0.93
C8—C7	1.379 (4)	C10—H10	0.93
C8—C9	1.426 (4)	C18—C19	1.385 (5)
C6—C7	1.393 (4)	C18—H18	0.93
C6—C5	1.427 (4)	C20—C19	1.363 (4)
C16—C17	1.369 (4)	C20—H20	0.93
C16—C21	1.380 (3)	C3—C4	1.396 (4)
C17—C18	1.380 (4)	C3—H3	0.93
C17—H17	0.93	C4—H4	0.93
C7—H7	0.93	C19—H19	0.93
C21—C20	1.382 (4)	C22—O2	1.203 (3)

C14—C13—C8	120.1 (2)	C3—C2—H2	119.2
C14—C13—C12	123.6 (2)	C1—C2—H2	119.2
C8—C13—C12	116.3 (2)	C4—C5—C6	121.3 (3)
C14—C1—C6	118.6 (2)	C4—C5—H5	119.3
C14—C1—C2	124.9 (2)	C6—C5—H5	119.3
C6—C1—C2	116.5 (2)	C11—C12—C13	121.4 (3)
C22—O1—C15	110.8 (2)	C11—C12—H12	119.3
O1—C15—C16	103.65 (19)	C13—C12—H12	119.3
O1—C15—C14	115.2 (2)	C12—C11—C10	121.8 (3)
C16—C15—C14	115.0 (2)	C12—C11—H11	119.1
O1—C15—H15	107.5	C10—C11—H11	119.1
C16—C15—H15	107.5	C10—C9—C8	121.3 (3)
C14—C15—H15	107.5	C10—C9—H9	119.4
C1—C14—C13	120.1 (2)	C8—C9—H9	119.4
C1—C14—C15	123.4 (2)	C9—C10—C11	119.4 (3)
C13—C14—C15	116.4 (2)	C9—C10—H10	120.3
C7—C8—C13	118.8 (2)	C11—C10—H10	120.3
C7—C8—C9	121.4 (3)	C17—C18—C19	121.7 (3)
C13—C8—C9	119.8 (3)	C17—C18—H18	119.2
C7—C6—C1	119.9 (2)	C19—C18—H18	119.2
C7—C6—C5	120.6 (3)	C19—C20—C21	117.9 (3)
C1—C6—C5	119.3 (2)	C19—C20—H20	121.1
C17—C16—C21	120.7 (3)	C21—C20—H20	121.1
C17—C16—C15	130.5 (2)	C2—C3—C4	121.3 (3)
C21—C16—C15	108.8 (2)	C2—C3—H3	119.3
C16—C17—C18	117.6 (3)	C4—C3—H3	119.3
C16—C17—H17	121.2	C5—C4—C3	119.8 (3)
C18—C17—H17	121.2	C5—C4—H4	120.1
C8—C7—C6	122.1 (2)	C3—C4—H4	120.1
C8—C7—H7	118.9	C20—C19—C18	120.6 (3)
C6—C7—H7	118.9	C20—C19—H19	119.7
C16—C21—C20	121.6 (3)	C18—C19—H19	119.7
C16—C21—C22	108.4 (2)	O2—C22—O1	120.8 (3)
C20—C21—C22	130.0 (3)	O2—C22—C21	131.0 (3)
C3—C2—C1	121.6 (3)	O1—C22—C21	108.2 (2)

C22—O1—C15—C16	−3.9 (2)	C5—C6—C7—C8	174.4 (2)
C22—O1—C15—C14	−130.4 (2)	C17—C16—C21—C20	−0.3 (4)
C6—C1—C14—C13	6.6 (3)	C15—C16—C21—C20	178.6 (2)
C2—C1—C14—C13	−170.9 (2)	C17—C16—C21—C22	−178.8 (2)
C6—C1—C14—C15	−176.8 (2)	C15—C16—C21—C22	0.1 (3)
C2—C1—C14—C15	5.7 (4)	C14—C1—C2—C3	178.4 (2)
C8—C13—C14—C1	−4.5 (3)	C6—C1—C2—C3	0.9 (4)
C12—C13—C14—C1	174.2 (2)	C7—C6—C5—C4	−174.3 (3)
C8—C13—C14—C15	178.6 (2)	C1—C6—C5—C4	2.2 (4)
C12—C13—C14—C15	−2.7 (3)	C14—C13—C12—C11	−178.5 (3)
O1—C15—C14—C1	35.6 (3)	C8—C13—C12—C11	0.2 (4)
C16—C15—C14—C1	−84.9 (3)	C13—C12—C11—C10	−0.8 (4)
O1—C15—C14—C13	−147.7 (2)	C7—C8—C9—C10	179.4 (3)
C16—C15—C14—C13	91.8 (3)	C13—C8—C9—C10	−0.8 (4)
C14—C13—C8—C7	−0.8 (3)	C8—C9—C10—C11	0.2 (4)
C12—C13—C8—C7	−179.6 (2)	C12—C11—C10—C9	0.6 (4)
C14—C13—C8—C9	179.4 (2)	C16—C17—C18—C19	−0.6 (4)
C12—C13—C8—C9	0.6 (3)	C16—C21—C20—C19	−0.2 (4)
C14—C1—C6—C7	−3.4 (3)	C22—C21—C20—C19	178.0 (3)
C2—C1—C6—C7	174.3 (2)	C1—C2—C3—C4	0.5 (4)
C14—C1—C6—C5	−179.9 (2)	C6—C5—C4—C3	−0.8 (4)
C2—C1—C6—C5	−2.2 (3)	C2—C3—C4—C5	−0.6 (4)
O1—C15—C16—C17	−179.1 (2)	C21—C20—C19—C18	0.2 (4)
C14—C15—C16—C17	−52.4 (3)	C17—C18—C19—C20	0.2 (4)
O1—C15—C16—C21	2.2 (2)	C15—O1—C22—O2	−176.0 (2)
C14—C15—C16—C21	128.9 (2)	C15—O1—C22—C21	4.1 (3)
C21—C16—C17—C18	0.7 (4)	C16—C21—C22—O2	177.6 (3)
C15—C16—C17—C18	−177.9 (2)	C20—C21—C22—O2	−0.8 (5)
C13—C8—C7—C6	4.2 (4)	C16—C21—C22—O1	−2.5 (3)
C9—C8—C7—C6	−176.1 (2)	C20—C21—C22—O1	179.1 (2)
C1—C6—C7—C8	−2.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1	0.93	2.33	2.914 (4)	120
C12—H12···Cg2ⁱ	0.93	2.94	3.746 (4)	147

Symmetry code: (i) −x+2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₄O₂
M_r	310.33
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	9.961 (4), 10.677 (5), 14.073 (5)
V (Å³)	1496.7 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.34 × 0.20 × 0.18

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	2462, 2462, 1469
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.705

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.125, 1.06
No. of reflections	2462
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.20

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), CAD-4 EXPRESS, XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), PLATON (Spek, 2003).

Selected bond lengths (Å) top

C1—C14	1.412 (3)	C15—C14	1.504 (3)
C1—C2	1.438 (3)	C16—C21	1.380 (3)
O1—C22	1.368 (3)	C21—C22	1.459 (4)
O1—C15	1.454 (3)	C22—O2	1.203 (3)
C15—C16	1.501 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1	0.93	2.33	2.914 (4)	120
C12—H12···Cg2ⁱ	0.93	2.94	3.746 (4)	147

Symmetry code: (i) −x+2, y−1/2, −z+1/2.

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