4-(9,10-Dioxo-9,10-dihydro­anthracen-1-yl)-4-oxobutanoic acid

Li, Y.; Lu, Q.-S.; Wei, R.-Q.; Liu, X.-N.; Li, F.-S.

doi:10.1107/S160053681004732X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3237

https://doi.org/10.1107/S160053681004732X

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4-(9,10-Dioxo-9,10-dihydroanthracen-1-yl)-4-oxobutanoic acid

Yi Li,^a Qi-Sheng Lu,^b Rong-Qing Wei,^a Xiao-Ning Liu ^a ^* and Fang-Shi Li ^b

^aCollege of Biotechnology, and Pharmaceutical Engineering, Nanjing University of Technology, Nanjing 210009, People's Republic of China, and ^bDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: xiaoningliu@163.com

(Received 11 November 2010; accepted 15 November 2010; online 20 November 2010)

In the title compound, C₁₈H₁₂O₅, the anthracene moiety is almost planar (r.m.s. deviation = 0.0399 Å). In the crystal, molecules are linked to each other by intermolecular O—H⋯O and weak C—H⋯O hydrogen bonds.

Related literature

For bond-length data, see: Allen et al. (1987 ). For applications of natural and synthetic anthraquinones, see: Brown (1980 ). For their activity, see: Johnson et al. (1997 ). For the synthesis, see: Inbasekaran et al. (1980 ).

Experimental

Crystal data

C₁₈H₁₂O₅
M_r = 308.28
Monoclinic, P 2₁ /n
a = 5.168 (1) Å
b = 19.523 (4) Å
c = 14.367 (3) Å
β = 99.58 (3)°
V = 1429.3 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.20 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.979, T_max = 0.990
2892 measured reflections
2593 independent reflections
1048 reflections with I > 2σ(I)
R_int = 0.077
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.078
wR(F²) = 0.161
S = 1.00
2593 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O4ⁱ	0.82	1.86	2.681 (6)	177
C7—H7A⋯O1ⁱⁱ	0.93	2.43	3.255 (7)	147
C16—H16A⋯O3ⁱⁱⁱ	0.97	2.48	3.375 (6)	154
Symmetry codes: (i) -x-1, -y, -z+1; (ii) -x+2, -y+1, -z+1; (iii) x+1, y, z.

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681004732X/bq2254sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681004732X/bq2254Isup2.hkl

checkCIF report

Comment top

Anthraquinone compounds are widely used in the chemical industry and medicine. Natural and synthetic anthraquinone compounds are used in food, cosmetics, hair color agent and textile dyes (Brown et al., 1980). In medicine, many of anthraquinones have diarrhea, anti-cell and other effects. The activity of anthraquinone derivatives has a great relationship with their planar frame structure (Johnson et al., 1997). We report here the crystal structure of the title compound, (I).

The molecular structure of (I) is shown in Fig. 1. The bond lengths and angles are within normal ranges (Allen et al., 1987). The anthrecene moiety is almost planar with an r.m.s. deviation of 0.0399 Å and a maximum deviation of 0.099 (4) Å for O2. In the crystal, molecules are linked to each other to form chains framework via intermolecular O—H···O and weak C—H···O hydrogen bonds.

Related literature top

For bond-length data, see: Allen et al. (1987). For applications of natural and synthetic anthraquinones, see: Brown (1980). For their activity, see: Johnson et al. (1997). For the synthesis, see: Inbasekaran et al. (1980);

Experimental top

The compound 4-(anthracen-1-yl)butanoic acid was synthesized by the method (Inbasekaran et al., 1980). The crystals of the title compound (I) were obtained by dissolving the compound 4-(anthracen-1-yl)butanoic acid in methanol (25 ml) in the presence of oxygen and evaporating the solvent slowly at room temperature for about 10 d.

Structure description top

For bond-length data, see: Allen et al. (1987). For applications of natural and synthetic anthraquinones, see: Brown (1980). For their activity, see: Johnson et al. (1997). For the synthesis, see: Inbasekaran et al. (1980);

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A drawing of the title molecular structure, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A packing diagram for (I). O—H···O and C—H···O intermolecular hydrogen bonds are shown by dashed lines.

4-(9,10-Dioxo-9,10-dihydroanthracen-1-yl)-4-oxobutanoic acid top

Crystal data top

C₁₈H₁₂O₅	F(000) = 640
M_r = 308.28	D_x = 1.433 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 5.168 (1) Å	θ = 8–12°
b = 19.523 (4) Å	µ = 0.11 mm⁻¹
c = 14.367 (3) Å	T = 293 K
β = 99.58 (3)°	Needle, colourless
V = 1429.3 (5) Å³	0.20 × 0.10 × 0.10 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	1048 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.077
Graphite monochromator	θ_max = 25.3°, θ_min = 1.8°
ω/2θ scans	h = 0→6
Absorption correction: ψ scan (North et al., 1968)	k = 0→23
T_min = 0.979, T_max = 0.990	l = −17→17
2892 measured reflections	3 standard reflections every 200 reflections
2593 independent reflections	intensity decay: 1%

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)] = 0.078	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.161	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.040P)²] where P = (F_o² + 2F_c²)/3
2593 reflections	(Δ/σ)_max < 0.001
208 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₈H₁₂O₅	V = 1429.3 (5) Å³
M_r = 308.28	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.168 (1) Å	µ = 0.11 mm⁻¹
b = 19.523 (4) Å	T = 293 K
c = 14.367 (3) Å	0.20 × 0.10 × 0.10 mm
β = 99.58 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1048 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.077
T_min = 0.979, T_max = 0.990	3 standard reflections every 200 reflections
2892 measured reflections	intensity decay: 1%
2593 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.078	0 restraints
wR(F²) = 0.161	H-atom parameters constrained
S = 1.00	Δρ_max = 0.21 e Å⁻³
2593 reflections	Δρ_min = −0.23 e Å⁻³
208 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
O1	0.6562 (8)	0.45510 (18)	0.4314 (3)	0.0687 (12)
O2	0.2523 (6)	0.26823 (17)	0.6393 (2)	0.0534 (10)
O3	−0.2936 (7)	0.21707 (19)	0.5131 (3)	0.0722 (13)
O4	−0.2825 (7)	0.04974 (17)	0.4635 (3)	0.0580 (11)
O5	−0.3291 (8)	0.0347 (2)	0.6115 (3)	0.0796 (13)
H5A	−0.4460	0.0090	0.5866	0.119*
C1	−0.0859 (11)	0.2918 (3)	0.3566 (4)	0.0590 (16)
H1A	−0.2305	0.2662	0.3293	0.071*
C2	0.0084 (12)	0.3422 (3)	0.3052 (4)	0.0656 (17)
H2A	−0.0687	0.3499	0.2429	0.079*
C3	0.2165 (11)	0.3814 (3)	0.3457 (4)	0.0556 (15)
H3A	0.2776	0.4161	0.3107	0.067*
C4	0.3375 (10)	0.3703 (2)	0.4378 (4)	0.0412 (13)
C5	0.5697 (10)	0.4127 (3)	0.4790 (4)	0.0467 (14)
C6	0.6852 (10)	0.4001 (2)	0.5783 (3)	0.0408 (13)
C7	0.9026 (11)	0.4383 (3)	0.6188 (4)	0.0555 (15)
H7A	0.9726	0.4712	0.5832	0.067*
C8	1.0149 (11)	0.4274 (3)	0.7122 (4)	0.0611 (17)
H8A	1.1575	0.4537	0.7397	0.073*
C9	0.9160 (11)	0.3780 (3)	0.7640 (4)	0.0640 (17)
H9A	0.9928	0.3702	0.8264	0.077*
C10	0.7023 (10)	0.3397 (3)	0.7236 (4)	0.0548 (15)
H10A	0.6372	0.3060	0.7593	0.066*
C11	0.5839 (9)	0.3501 (2)	0.6323 (4)	0.0425 (13)
C12	0.3528 (10)	0.3090 (2)	0.5912 (4)	0.0425 (13)
C13	0.2415 (9)	0.3191 (2)	0.4900 (3)	0.0365 (12)
C14	0.0322 (9)	0.2783 (2)	0.4497 (3)	0.0392 (12)
C15	−0.0699 (10)	0.2173 (3)	0.4968 (4)	0.0484 (14)
C16	0.0972 (9)	0.1546 (2)	0.5123 (4)	0.0502 (14)
H16A	0.2779	0.1679	0.5340	0.060*
H16B	0.0898	0.1305	0.4529	0.060*
C17	0.0093 (10)	0.1069 (2)	0.5841 (4)	0.0526 (15)
H17A	0.1567	0.0784	0.6109	0.063*
H17B	−0.0394	0.1343	0.6348	0.063*
C18	−0.2128 (10)	0.0622 (2)	0.5464 (4)	0.0493 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.081 (3)	0.059 (3)	0.071 (3)	−0.018 (2)	0.029 (2)	0.018 (2)
O2	0.061 (3)	0.053 (2)	0.048 (2)	−0.0200 (19)	0.012 (2)	0.0045 (18)
O3	0.035 (2)	0.068 (3)	0.119 (4)	−0.007 (2)	0.027 (2)	−0.005 (2)
O4	0.060 (3)	0.061 (2)	0.049 (2)	−0.026 (2)	−0.003 (2)	0.0015 (19)
O5	0.088 (3)	0.086 (3)	0.067 (3)	−0.036 (3)	0.021 (2)	−0.005 (2)
C1	0.049 (4)	0.060 (4)	0.065 (4)	0.000 (3)	0.001 (3)	−0.015 (3)
C2	0.077 (5)	0.069 (4)	0.044 (4)	0.003 (4)	−0.006 (3)	−0.002 (3)
C3	0.072 (4)	0.051 (4)	0.046 (4)	0.000 (3)	0.018 (3)	0.007 (3)
C4	0.043 (3)	0.041 (3)	0.041 (3)	−0.004 (3)	0.011 (3)	0.003 (2)
C5	0.054 (4)	0.038 (3)	0.052 (4)	0.000 (3)	0.019 (3)	0.002 (3)
C6	0.045 (3)	0.030 (3)	0.050 (3)	−0.004 (3)	0.014 (3)	−0.005 (3)
C7	0.053 (4)	0.046 (3)	0.073 (4)	−0.006 (3)	0.025 (3)	−0.014 (3)
C8	0.051 (4)	0.062 (4)	0.069 (4)	−0.005 (3)	0.006 (3)	−0.019 (3)
C9	0.070 (4)	0.068 (4)	0.051 (4)	−0.012 (4)	0.002 (3)	−0.011 (3)
C10	0.054 (4)	0.062 (4)	0.046 (4)	−0.010 (3)	0.000 (3)	−0.005 (3)
C11	0.038 (3)	0.039 (3)	0.050 (3)	0.002 (3)	0.006 (3)	−0.009 (3)
C12	0.041 (3)	0.037 (3)	0.052 (4)	−0.002 (3)	0.013 (3)	−0.003 (3)
C13	0.031 (3)	0.041 (3)	0.038 (3)	0.003 (2)	0.008 (2)	−0.009 (3)
C14	0.031 (3)	0.039 (3)	0.047 (3)	0.005 (3)	0.001 (3)	−0.006 (3)
C15	0.039 (3)	0.039 (3)	0.067 (4)	−0.003 (3)	0.008 (3)	−0.009 (3)
C16	0.038 (3)	0.044 (3)	0.071 (4)	−0.009 (3)	0.016 (3)	−0.013 (3)
C17	0.051 (3)	0.038 (3)	0.068 (4)	−0.007 (3)	0.008 (3)	−0.006 (3)
C18	0.048 (4)	0.038 (3)	0.061 (4)	−0.010 (3)	0.007 (3)	0.004 (3)

Geometric parameters (Å, º) top

O1—C5	1.206 (5)	C7—H7A	0.9300
O2—C12	1.225 (5)	C8—C9	1.368 (7)
O3—C15	1.218 (5)	C8—H8A	0.9300
O4—C18	1.210 (6)	C9—C10	1.379 (6)
O5—C18	1.308 (6)	C9—H9A	0.9300
O5—H5A	0.8200	C10—C11	1.367 (6)
C1—C2	1.367 (7)	C10—H10A	0.9300
C1—C14	1.400 (6)	C11—C12	1.478 (6)
C1—H1A	0.9300	C12—C13	1.484 (6)
C2—C3	1.368 (7)	C13—C14	1.389 (6)
C2—H2A	0.9300	C14—C15	1.508 (6)
C3—C4	1.383 (6)	C15—C16	1.494 (6)
C3—H3A	0.9300	C16—C17	1.513 (6)
C4—C13	1.391 (6)	C16—H16A	0.9700
C4—C5	1.496 (6)	C16—H16B	0.9700
C5—C6	1.472 (6)	C17—C18	1.472 (6)
C6—C7	1.393 (6)	C17—H17A	0.9700
C6—C11	1.402 (6)	C17—H17B	0.9700
C7—C8	1.388 (7)

C18—O5—H5A	109.5	C10—C11—C6	119.1 (5)
C2—C1—C14	120.8 (5)	C10—C11—C12	120.4 (5)
C2—C1—H1A	119.6	C6—C11—C12	120.5 (5)
C14—C1—H1A	119.6	O2—C12—C11	121.1 (5)
C1—C2—C3	119.9 (5)	O2—C12—C13	120.5 (5)
C1—C2—H2A	120.0	C11—C12—C13	118.4 (4)
C3—C2—H2A	120.0	C14—C13—C4	120.7 (5)
C2—C3—C4	121.2 (5)	C14—C13—C12	118.7 (5)
C2—C3—H3A	119.4	C4—C13—C12	120.6 (5)
C4—C3—H3A	119.4	C13—C14—C1	118.4 (5)
C3—C4—C13	118.9 (5)	C13—C14—C15	124.9 (5)
C3—C4—C5	119.8 (5)	C1—C14—C15	116.6 (5)
C13—C4—C5	121.3 (5)	O3—C15—C16	120.8 (5)
O1—C5—C6	122.4 (5)	O3—C15—C14	120.3 (5)
O1—C5—C4	120.2 (5)	C16—C15—C14	118.6 (4)
C6—C5—C4	117.4 (5)	C15—C16—C17	112.0 (4)
C7—C6—C11	119.4 (5)	C15—C16—H16A	109.2
C7—C6—C5	118.9 (5)	C17—C16—H16A	109.2
C11—C6—C5	121.6 (5)	C15—C16—H16B	109.2
C8—C7—C6	120.0 (5)	C17—C16—H16B	109.2
C8—C7—H7A	120.0	H16A—C16—H16B	107.9
C6—C7—H7A	120.0	C18—C17—C16	114.8 (5)
C9—C8—C7	120.1 (6)	C18—C17—H17A	108.6
C9—C8—H8A	120.0	C16—C17—H17A	108.6
C7—C8—H8A	120.0	C18—C17—H17B	108.6
C8—C9—C10	119.9 (6)	C16—C17—H17B	108.6
C8—C9—H9A	120.1	H17A—C17—H17B	107.6
C10—C9—H9A	120.1	O4—C18—O5	121.6 (5)
C11—C10—C9	121.5 (6)	O4—C18—C17	124.5 (5)
C11—C10—H10A	119.2	O5—C18—C17	113.8 (5)
C9—C10—H10A	119.2

C14—C1—C2—C3	−1.8 (8)	C10—C11—C12—C13	−176.1 (4)
C1—C2—C3—C4	1.1 (8)	C6—C11—C12—C13	3.6 (6)
C2—C3—C4—C13	−1.2 (8)	C3—C4—C13—C14	1.8 (7)
C2—C3—C4—C5	178.2 (5)	C5—C4—C13—C14	−177.5 (4)
C3—C4—C5—O1	−2.2 (7)	C3—C4—C13—C12	−175.4 (4)
C13—C4—C5—O1	177.1 (5)	C5—C4—C13—C12	5.3 (7)
C3—C4—C5—C6	178.1 (4)	O2—C12—C13—C14	−4.1 (7)
C13—C4—C5—C6	−2.6 (7)	C11—C12—C13—C14	177.0 (4)
O1—C5—C6—C7	−0.1 (7)	O2—C12—C13—C4	173.2 (4)
C4—C5—C6—C7	179.6 (4)	C11—C12—C13—C4	−5.8 (6)
O1—C5—C6—C11	−179.3 (5)	C4—C13—C14—C1	−2.5 (7)
C4—C5—C6—C11	0.4 (7)	C12—C13—C14—C1	174.8 (4)
C11—C6—C7—C8	−0.8 (7)	C4—C13—C14—C15	173.8 (4)
C5—C6—C7—C8	180.0 (5)	C12—C13—C14—C15	−8.9 (7)
C6—C7—C8—C9	1.5 (8)	C2—C1—C14—C13	2.4 (7)
C7—C8—C9—C10	−0.9 (8)	C2—C1—C14—C15	−174.2 (5)
C8—C9—C10—C11	−0.4 (8)	C13—C14—C15—O3	118.0 (6)
C9—C10—C11—C6	1.1 (8)	C1—C14—C15—O3	−65.7 (7)
C9—C10—C11—C12	−179.2 (5)	C13—C14—C15—C16	−69.1 (6)
C7—C6—C11—C10	−0.4 (7)	C1—C14—C15—C16	107.2 (5)
C5—C6—C11—C10	178.7 (5)	O3—C15—C16—C17	−24.0 (7)
C7—C6—C11—C12	179.8 (4)	C14—C15—C16—C17	163.1 (4)
C5—C6—C11—C12	−1.1 (7)	C15—C16—C17—C18	81.7 (5)
C10—C11—C12—O2	4.9 (7)	C16—C17—C18—O4	18.2 (7)
C6—C11—C12—O2	−175.3 (4)	C16—C17—C18—O5	−163.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O4ⁱ	0.82	1.86	2.681 (6)	177
C7—H7A···O1ⁱⁱ	0.93	2.43	3.255 (7)	147
C16—H16A···O3ⁱⁱⁱ	0.97	2.48	3.375 (6)	154

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₂O₅
M_r	308.28
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	5.168 (1), 19.523 (4), 14.367 (3)
β (°)	99.58 (3)
V (Å³)	1429.3 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.979, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	2892, 2593, 1048
R_int	0.077
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.078, 0.161, 1.00
No. of reflections	2593
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.23

Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O4ⁱ	0.82	1.86	2.681 (6)	177
C7—H7A···O1ⁱⁱ	0.93	2.43	3.255 (7)	147
C16—H16A···O3ⁱⁱⁱ	0.97	2.48	3.375 (6)	154

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

Acknowledgements

This work was supported by the National High-tech R&D Program of China (Nos. 2007AA02Z200 and 2007AA06A402).

References

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