Benzo[a]fluoren-11-one

Sun, D.; Luo, G.-G.; Xie, S.-Y.; Huang, R.-B.; Zheng, L.-S.

doi:10.1107/S1600536808020989

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1468

doi:10.1107/S1600536808020989

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Benzo[a]fluoren-11-one

Di Sun,^a Geng-Geng Luo,^a Su-Yuan Xie,^a Rong-Bin Huang ^a ^* and Lan-Sun Zheng ^b

^aDepartment of Chemistry, Xiamen University, Xiamen 361005, People's Republic of China, and ^bState Key Laboratory for Physical Chemistry of Solid Surfaces, Xiamen University, Xiamen 361005, People's Republic of China
^*Correspondence e-mail: rbhuang@xmu.edu.cn

(Received 2 July 2008; accepted 7 July 2008; online 12 July 2008)

The molecule of the title compound, C₁₇H₁₀O, is nearly planar, the largest deviation from the mean plane being 0.06 Å. The crystal structure is governed by π–π interactions, with centroid–centroid distances ranging from .559 to 3.730 Å.

Related literature

For related literature, see: Banik et al. (2006 ); Huang et al. (1997 ); Peng et al. (2001 ); Streitweiser & Brown (1988 ); Xie et al. (2001 ).

Experimental

Crystal data

C₁₇H₁₀O
M_r = 230.25
Monoclinic, P 2₁ /c
a = 9.3852 (4) Å
b = 7.1165 (3) Å
c = 16.8809 (7) Å
β = 99.278 (5)°
V = 1112.72 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 173 (2) K
0.55 × 0.20 × 0.20 mm

Data collection

Oxford Gemini S Ultra diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.955, T_max = 0.983
4736 measured reflections
2134 independent reflections
1433 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.094
S = 1.01
2134 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
π–π Interactions (Å)

	Centroid–centroid	Interplanar distance	Slippage
Cg1⋯Cg1ⁱ	3.683	3.46	1.26
Cg1⋯Cg2ⁱ	3.627	3.48	0.98
Cg1⋯Cg4ⁱⁱ	3.559	3.38	1.06
Cg2⋯Cg3ⁱ	3.730	3.49	1.23
Cg3⋯Cg4ⁱⁱ	3.667	3.38	1.31
Symmetry codes: (i) -x, 1-y, -z; (ii) 1-x, 1-y, -z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); data reduction: CrysAlis RED; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808020989/dn2363sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808020989/dn2363Isup2.hkl

checkCIF report

Comment top

Benzo[a]fluoren-11-one, C₁₇H₁₀O, (Scheme), can be readily synthesed by oxidation of the corresponding hydrocarbon with different oxidants, such as NaBiO₃(Banik et al., 2006), or by Friedel-Crafts ring closure reaction(Streitwieser et al., 1988). But its crystal structure determination has not been carried out yet. During the past decade, our group has used various non-organic methods, such as high-voltage electric discharge in liquid (Huang et al., 1997), vaporized (Xie et al., 2001) chloroform and CCl₄ and solvothermal reaction (Peng et al., 2001) to generate and trap a family of perchlorinated fullerene fragments. Recently in our low pressure premixed benzene-oxygen combustion system, we generated the compound, C₁₇H₁₀O, and isolated it. We report here the synthesis and crystal structure of the compound.

The title compound, C₁₇H₁₀O, is built up from four fused rings. The whole molecule is nearly planar with the largest deviations from the mean plane being 0.06Å (Fig. 1). The crystal packing is governed by π-π interactions (Table 1).

Related literature top

For related literature, see: Banik et al. (2006); Huang et al. (1997); Peng et al. (2001); Streitwieser & Brown (1988); Xie et al. (2001).

Experimental top

The compound was prepared in low pressure pre-mixed benzene-oxygen flames. The premixed flames conditions for the soot production as the following range: atom C/O ratio:1–2; combustion chamber pressure: 350torr. The soot collected from the water-cooled coping was extracted with toluene using an ultrasonic bath under room temperature, the resulting dark-brown solution was separated and purified by multi-stage high-preformance liquid chromatography(HPLC), finally we obtained one of fractions contained pure C₁₇H₁₀O. The red single crystals suitable for X-ray diffraction crystallized from toluene at room temperature. The product was analyzed by Atmospheric-Pressure Chemical Ionization(APCI) mass spectrometry(negative mode). The molecular peak appeared at a mass/charge ratio of 230.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); 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).

Figures top

Fig. 1. ORTEP Molecular view of compound I. Thermal ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.

Benzo[a]fluoren-11-one top

Crystal data top

C₁₇H₁₀O	F(000) = 480
M_r = 230.25	D_x = 1.374 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1792 reflections
a = 9.3852 (4) Å	θ = 2.7–32.6°
b = 7.1165 (3) Å	µ = 0.08 mm⁻¹
c = 16.8809 (7) Å	T = 173 K
β = 99.278 (5)°	Prism, red
V = 1112.72 (8) Å³	0.55 × 0.20 × 0.20 mm
Z = 4

Data collection top

Oxford Gemini S Ultra diffractometer	2134 independent reflections
Radiation source: fine-focus sealed tube	1433 reflections with > 2σ
Graphite monochromator	R_int = 0.034
ω scans	θ_max = 26.0°, θ_min = 3.6°
Absorption correction: empirical (using intensity measurements) (CrysAlis RED; Oxford Diffraction, 2007)	h = −11→10
T_min = 0.955, T_max = 0.983	k = −8→8
4736 measured reflections	l = −20→20

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.094	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0409P)²] where P = (F_o² + 2F_c²)/3
2134 reflections	(Δ/σ)_max < 0.001
163 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₇H₁₀O	V = 1112.72 (8) Å³
M_r = 230.25	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.3852 (4) Å	µ = 0.08 mm⁻¹
b = 7.1165 (3) Å	T = 173 K
c = 16.8809 (7) Å	0.55 × 0.20 × 0.20 mm
β = 99.278 (5)°

Data collection top

Oxford Gemini S Ultra diffractometer	2134 independent reflections
Absorption correction: empirical (using intensity measurements) (CrysAlis RED; Oxford Diffraction, 2007)	1433 reflections with > 2σ
T_min = 0.955, T_max = 0.983	R_int = 0.034
4736 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.094	H-atom parameters constrained
S = 1.01	Δρ_max = 0.15 e Å⁻³
2134 reflections	Δρ_min = −0.17 e Å⁻³
163 parameters

Special details top

Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. CrysAlis RED (Oxford Diffraction, 2007)

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
O1	0.20866 (13)	0.18498 (17)	−0.07292 (8)	0.0441 (4)
C1	−0.02937 (18)	0.4405 (3)	−0.16653 (10)	0.0378 (5)
H1A	−0.0396	0.3189	−0.1900	0.045*
C2	−0.11989 (19)	0.5866 (3)	−0.19725 (11)	0.0438 (5)
H2A	−0.1930	0.5651	−0.2422	0.053*
C3	−0.10410 (18)	0.7630 (3)	−0.16279 (11)	0.0411 (5)
H3A	−0.1668	0.8614	−0.1846	0.049*
C4	0.00180 (17)	0.7996 (3)	−0.09676 (11)	0.0356 (4)
H4A	0.0125	0.9214	−0.0735	0.043*
C5	0.26877 (16)	0.7875 (2)	0.05511 (10)	0.0302 (4)
H5A	0.2280	0.9100	0.0512	0.036*
C6	0.38358 (17)	0.7465 (2)	0.11267 (10)	0.0333 (4)
H6A	0.4220	0.8422	0.1492	0.040*
C7	0.56835 (17)	0.5255 (3)	0.17902 (10)	0.0368 (5)
H7A	0.6054	0.6201	0.2164	0.044*
C8	0.63221 (18)	0.3530 (3)	0.18308 (11)	0.0395 (5)
H8A	0.7138	0.3288	0.2229	0.047*
C9	0.57847 (17)	0.2119 (3)	0.12911 (11)	0.0397 (5)
H9A	0.6246	0.0927	0.1321	0.048*
C10	0.46019 (17)	0.2432 (3)	0.07188 (11)	0.0346 (4)
H10A	0.4238	0.1450	0.0361	0.041*
C11	0.18804 (17)	0.3497 (2)	−0.05773 (10)	0.0313 (4)
C12	0.07505 (15)	0.4757 (2)	−0.10158 (9)	0.0291 (4)
C13	0.09063 (15)	0.6536 (2)	−0.06621 (10)	0.0282 (4)
C14	0.21217 (16)	0.6458 (2)	0.00190 (9)	0.0272 (4)
C15	0.27059 (16)	0.4674 (2)	0.00659 (9)	0.0275 (4)
C16	0.39179 (16)	0.4204 (2)	0.06560 (9)	0.0278 (4)
C17	0.44778 (16)	0.5651 (3)	0.11987 (10)	0.0304 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0524 (8)	0.0301 (8)	0.0491 (8)	−0.0072 (6)	0.0059 (6)	−0.0097 (7)
C1	0.0367 (9)	0.0464 (12)	0.0317 (9)	−0.0128 (9)	0.0093 (8)	−0.0059 (10)
C2	0.0361 (10)	0.0628 (15)	0.0302 (9)	−0.0109 (10)	−0.0011 (8)	0.0009 (11)
C3	0.0332 (9)	0.0504 (13)	0.0389 (10)	0.0002 (9)	0.0032 (9)	0.0091 (11)
C4	0.0329 (9)	0.0376 (10)	0.0369 (10)	−0.0036 (8)	0.0076 (8)	0.0004 (9)
C5	0.0322 (8)	0.0281 (9)	0.0315 (9)	−0.0046 (8)	0.0090 (8)	−0.0040 (9)
C6	0.0380 (9)	0.0355 (10)	0.0271 (9)	−0.0106 (8)	0.0072 (8)	−0.0086 (9)
C7	0.0354 (9)	0.0485 (12)	0.0271 (9)	−0.0076 (9)	0.0070 (8)	−0.0004 (10)
C8	0.0317 (9)	0.0562 (14)	0.0297 (10)	−0.0007 (9)	0.0021 (8)	0.0106 (10)
C9	0.0378 (10)	0.0390 (11)	0.0445 (11)	0.0035 (9)	0.0130 (9)	0.0117 (10)
C10	0.0354 (9)	0.0340 (11)	0.0366 (10)	−0.0079 (8)	0.0128 (8)	0.0000 (9)
C11	0.0331 (9)	0.0311 (10)	0.0319 (9)	−0.0098 (8)	0.0113 (8)	−0.0029 (9)
C12	0.0288 (8)	0.0343 (10)	0.0257 (9)	−0.0069 (8)	0.0092 (8)	−0.0011 (9)
C13	0.0244 (8)	0.0370 (11)	0.0245 (8)	−0.0073 (8)	0.0078 (7)	−0.0012 (9)
C14	0.0256 (8)	0.0316 (10)	0.0260 (9)	−0.0074 (7)	0.0087 (7)	−0.0007 (9)
C15	0.0294 (8)	0.0276 (9)	0.0277 (9)	−0.0080 (8)	0.0111 (7)	−0.0011 (9)
C16	0.0261 (8)	0.0320 (10)	0.0272 (9)	−0.0047 (7)	0.0095 (7)	0.0041 (9)
C17	0.0282 (9)	0.0385 (11)	0.0258 (9)	−0.0061 (8)	0.0083 (8)	0.0015 (9)

Geometric parameters (Å, º) top

O1—C11	1.222 (2)	C7—C17	1.412 (2)
C1—C12	1.371 (2)	C7—H7A	0.9500
C1—C2	1.389 (3)	C8—C9	1.395 (3)
C1—H1A	0.9500	C8—H8A	0.9500
C2—C3	1.381 (3)	C9—C10	1.367 (2)
C2—H2A	0.9500	C9—H9A	0.9500
C3—C4	1.393 (2)	C10—C16	1.411 (2)
C3—H3A	0.9500	C10—H10A	0.9500
C4—C13	1.380 (2)	C11—C15	1.486 (2)
C4—H4A	0.9500	C11—C12	1.491 (2)
C5—C6	1.361 (2)	C12—C13	1.397 (2)
C5—C14	1.397 (2)	C13—C14	1.484 (2)
C5—H5A	0.9500	C14—C15	1.380 (2)
C6—C17	1.421 (2)	C15—C16	1.426 (2)
C6—H6A	0.9500	C16—C17	1.422 (2)
C7—C8	1.362 (3)

C12—C1—C2	118.49 (18)	C8—C9—H9A	119.6
C12—C1—H1A	120.8	C9—C10—C16	120.40 (17)
C2—C1—H1A	120.8	C9—C10—H10A	119.8
C3—C2—C1	120.36 (17)	C16—C10—H10A	119.8
C3—C2—H2A	119.8	O1—C11—C15	127.75 (16)
C1—C2—H2A	119.8	O1—C11—C12	126.62 (16)
C2—C3—C4	121.42 (18)	C15—C11—C12	105.62 (14)
C2—C3—H3A	119.3	C1—C12—C13	121.30 (16)
C4—C3—H3A	119.3	C1—C12—C11	130.30 (16)
C13—C4—C3	117.91 (17)	C13—C12—C11	108.39 (13)
C13—C4—H4A	121.0	C4—C13—C12	120.51 (15)
C3—C4—H4A	121.0	C4—C13—C14	131.32 (16)
C6—C5—C14	118.63 (16)	C12—C13—C14	108.15 (15)
C6—C5—H5A	120.7	C15—C14—C5	121.40 (15)
C14—C5—H5A	120.7	C15—C14—C13	109.10 (15)
C5—C6—C17	122.13 (16)	C5—C14—C13	129.49 (16)
C5—C6—H6A	118.9	C14—C15—C16	121.37 (15)
C17—C6—H6A	118.9	C14—C15—C11	108.72 (14)
C8—C7—C17	120.77 (17)	C16—C15—C11	129.91 (15)
C8—C7—H7A	119.6	C10—C16—C17	118.86 (15)
C17—C7—H7A	119.6	C10—C16—C15	124.34 (15)
C7—C8—C9	120.38 (16)	C17—C16—C15	116.79 (15)
C7—C8—H8A	119.8	C7—C17—C6	121.51 (16)
C9—C8—H8A	119.8	C7—C17—C16	118.79 (16)
C10—C9—C8	120.77 (17)	C6—C17—C16	119.69 (14)
C10—C9—H9A	119.6

Experimental details

Crystal data
Chemical formula	C₁₇H₁₀O
M_r	230.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	9.3852 (4), 7.1165 (3), 16.8809 (7)
β (°)	99.278 (5)
V (Å³)	1112.72 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.55 × 0.20 × 0.20

Data collection
Diffractometer	Oxford Gemini S Ultra diffractometer
Absorption correction	Empirical (using intensity measurements) (CrysAlis RED; Oxford Diffraction, 2007)
T_min, T_max	0.955, 0.983
No. of measured, independent and observed ( > 2σ) reflections	4736, 2134, 1433
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.094, 1.01
No. of reflections	2134
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.17

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

π–π Interactions (Å) top

	Centroid–centroid	Interplanar distance	Slippage
Cg1···Cg1ⁱ	3.683	3.46	1.26
Cg1···Cg2ⁱ	3.627	3.48	0.98
Cg1···Cg4ⁱⁱ	3.559	3.38	1.06
Cg2···Cg3ⁱ	3.730	3.49	1.23
Cg3···Cg4ⁱⁱ	3.667	3.38	1.31

Symmetry codes: (i) -x, 1-y, -z; (ii) 1-x, 1-y, -z.

References

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