Literature DB >> 21203182

Benzo[a]fluoren-11-one.

Di Sun, Geng-Geng Luo, Su-Yuan Xie, Rong-Bin Huang, Lan-Sun Zheng.

Abstract

The mol-ecule of the title compound, C(17)H(10)O, is nearly planar, the largest deviation from the mean plane being 0.06 Å. The crystal structure is governed by π-π inter-actions, with centroid-centroid distances ranging from .559 to 3.730 Å.

Entities: Chemical Disease Gene

Year: 2008 PMID： 21203182 PMCID： PMC2962100 DOI： 10.1107/S1600536808020989

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

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 = 230.25 Monoclinic, 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 ▶) 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[F 2 > 2σ(F 2)] = 0.047 wR(F 2) = 0.094 S = 1.01 2134 reflections 163 parameters H-atom parameters constrained Δρmax = 0.15 e Å−3 Δρmin = −0.17 e Å−3 Data collection: CrysAlis CCD (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); 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. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808020989/dn2363sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020989/dn2363Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₇H₁₀O	F₀₀₀ = 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 = 2.7–32.6º
b = 7.1165 (3) Å	µ = 0.08 mm⁻¹
c = 16.8809 (7) Å	T = 173 (2) K
β = 99.278 (5)º	Prism, red
V = 1112.72 (8) Å³	0.55 × 0.20 × 0.20 mm
Z = 4

Oxford Gemini S Ultra diffractometer	2134 independent reflections
Radiation source: fine-focus sealed tube	1433 reflections with > 2σ
Monochromator: graphite	R_int = 0.034
T = 173(2) K	θ_max = 26.0º
ω scans	θ_min = 3.6º
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 on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.047	H-atom parameters constrained
wR(F²) = 0.094	w = 1/[σ²(F_o²) + (0.0409P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
2134 reflections	Δρ_max = 0.15 e Å⁻³
163 parameters	Δρ_min = −0.17 e Å⁻³
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	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)

	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)

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

	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

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) ; (ii)

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Authors: George M Sheldrick
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