(S)-(+)-1-(2-Bromo­phen­yl)ethanol

Staples, R.J.; Medley, J.W.

doi:10.1107/S1600536807059260

organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o301

https://doi.org/10.1107/S1600536807059260

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(S)-(+)-1-(2-Bromophenyl)ethanol

Richard J. Staples ^a ^*‡ and Jonathan W. Medley ^a

^aHarvard University, Department of Chemistry and Chemical Biology, Cambridge, MA 02138, USA
^*Correspondence e-mail: staples@chemistry.msu.edu

(Received 26 October 2007; accepted 14 November 2007; online 18 December 2007)

The title compound, C₈H₉BrO, crystallizes with two molecules in the asymmetric unit. The structure displays O—H⋯O hydrogen bonding, generating zigzag chains evolving around a screw axis along [100].

Related literature

For literature on related complexes, see: Angiolini et al. (1995 ); Venkatachalam et al. (2005 ). For related literature, see: Staples (2001 ); Staples & George (2005 ); Staples & Huang (2002 ).

Experimental

Crystal data

C₈H₉BrO
M_r = 201.06
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.3235 (6) Å
b = 11.9440 (11) Å
c = 19.3583 (18) Å
V = 1693.3 (3) Å³
Z = 8
Mo Kα radiation
μ = 4.79 mm⁻¹
T = 193 (2) K
0.20 × 0.08 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ) T_min = 0.434, T_max = 0.680
12365 measured reflections
4195 independent reflections
3420 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.080
S = 1.03
4195 reflections
185 parameters
H-atom parameters constrained
Δρ_max = 0.67 e Å⁻³
Δρ_min = −0.33 e Å⁻³
Absolute structure: Flack (1983 ), with 1788 Friedel pairs
Flack parameter: −0.004 (10)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1A—H1A⋯O1Bⁱ	0.84	1.81	2.645 (3)	177
O1B—H1B⋯O1Aⁱⁱ	0.84	1.81	2.627 (3)	165
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ ; (ii) x+1, y+1, z.

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 2003 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536807059260/bg2123sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807059260/bg2123Isup2.hkl

checkCIF report

Comment top

We have been studying the crystallization properties of enantiomeric compounds and their racemic mixtures, as well as the effect of hydrogen bonding on their crystallization behaviour (Staples and Huang, 2002; Staples and George, 2005). In particular we are interested in those compounds that can act as ligands to transition metal complexes (Staples, 2001). In the course of this study we have structurally characterized the tittle compound, C₈H₉BrO (I). We have also crystallized the enantiomeric compound, R-(-)-2-bromo-alpha-methyl benzylalcohol, which will be reported later.

S-(+)-2-bromo-alpha-methyl benzylalcohol crystallizes with two molecules in the assymmetric unit and presents intermolecular hydrogen bonding, a fact which can dictate the crystallization as well as solvation properties. It is our hope that we can use this compound for further studies of crystallization and coordination chemistry.

The stucture of S-(+)-2-bromo-alpha-methyl benzylalcohol is shown in Fgure 1. The compound exhibits standard bond lengths and angles, similar to those in closely related compounds (Angiolini et al., 1995; Venkatachalam et al.,2005). It displays hydrogen bonding interactions with neighboring molecules (Table 1), to form a linear type of hydrogen bonding structure (Figure 2). The outcome is a zigzag chain structure containing both unique molecules and evolving around a screw axis along [100].

Related literature top

For literature on related complexes, see: Angiolini et al. (1995); Venkatachalam et al. (2005). For related literature, see: Staples (2001); Staples & George (2005); Staples & Huang (2002).

Experimental top

The title compound was purchased from Aldrich and the crystals were grown by a slow evaporation of a dichloromethane solution.

Structure description top

For literature on related complexes, see: Angiolini et al. (1995); Venkatachalam et al. (2005). For related literature, see: Staples (2001); Staples & George (2005); Staples & Huang (2002).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL (Bruker, 2000).

Figures top

	Fig. 1. Thermal ellipsoid plot (50% probability) of the title compound.
	Fig. 2. Packing diagram of the title compund showing the linear hydrogen bonding interaction.

(S)-(+)-1-(2-Bromophenyl)ethanol top

Crystal data top

C₈H₉BrO	F(000) = 800
M_r = 201.06	D_x = 1.577 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3839 reflections
a = 7.3235 (6) Å	θ = 3.0–23.9°
b = 11.9440 (11) Å	µ = 4.79 mm⁻¹
c = 19.3583 (18) Å	T = 193 K
V = 1693.3 (3) Å³	Needle, white
Z = 8	0.20 × 0.08 × 0.08 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4195 independent reflections
Radiation source: normal-focus sealed tube	3420 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
phi and ω scans	θ_max = 28.3°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −7→9
T_min = 0.434, T_max = 0.680	k = −15→12
12365 measured reflections	l = −25→21

Refinement top

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)] = 0.033	H-atom parameters constrained
wR(F²) = 0.080	w = 1/[σ²(F_o²) + (0.0359P)²] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
4195 reflections	Δρ_max = 0.67 e Å⁻³
185 parameters	Δρ_min = −0.33 e Å⁻³
0 restraints	Absolute structure: Flack, 1983, 1788 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.004 (10)

Crystal data top

C₈H₉BrO	V = 1693.3 (3) Å³
M_r = 201.06	Z = 8
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.3235 (6) Å	µ = 4.79 mm⁻¹
b = 11.9440 (11) Å	T = 193 K
c = 19.3583 (18) Å	0.20 × 0.08 × 0.08 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4195 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	3420 reflections with I > 2σ(I)
T_min = 0.434, T_max = 0.680	R_int = 0.027
12365 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.080	Δρ_max = 0.67 e Å⁻³
S = 1.03	Δρ_min = −0.33 e Å⁻³
4195 reflections	Absolute structure: Flack, 1983, 1788 Friedel pairs
185 parameters	Absolute structure parameter: −0.004 (10)
0 restraints

Special details top

Experimental. Data was collected using a BRUKER SMART CCD (charge coupled device) based diffractometer equipped with an Oxford low-temperature apparatus operating at 193 K. A suitable crystal was chosen and mounted on a glass fiber using grease. Data were measured using omega scans of 0.3° per frame for 30 s, such that a hemisphere was collected. A total of 1271 frames were collected with a final resolution of 0.76 Å. The first 50 frames were recollected at the end of data collection to monitor for decay. Cell parameters were retrieved using SMART software and refined using SAINT on all observed reflections. Data reduction was performed using the SAINT software which corrects for Lp and decay. The structures are solved by the direct method using the SHELX90 program and refined by least squares method on F2 SHELXL93, incorporated in SHELXTL V6.1.

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
Br1A	0.13612 (6)	0.57908 (3)	0.20047 (2)	0.07072 (14)
O1A	0.0096 (3)	0.29862 (17)	0.05433 (10)	0.0494 (5)
H1A	0.1035	0.3182	0.0326	0.074*
C1A	0.2226 (4)	0.4285 (2)	0.20561 (15)	0.0458 (7)
C2A	0.1479 (4)	0.3466 (2)	0.16427 (14)	0.0403 (6)
C3A	0.2190 (5)	0.2392 (3)	0.17111 (16)	0.0553 (8)
H3A	0.1718	0.1807	0.1431	0.066*
C4A	0.3564 (5)	0.2154 (4)	0.2175 (2)	0.0701 (10)
H4A	0.4020	0.1413	0.2217	0.084*
C5A	0.4272 (5)	0.3004 (4)	0.25806 (19)	0.0675 (10)
H5A	0.5222	0.2843	0.2900	0.081*
C6A	0.3622 (4)	0.4066 (3)	0.25272 (17)	0.0606 (9)
H6A	0.4110	0.4649	0.2806	0.073*
C7A	−0.0089 (4)	0.3657 (2)	0.11472 (14)	0.0414 (6)
H7A	−0.0110	0.4464	0.1010	0.050*
C8A	−0.1898 (4)	0.3363 (3)	0.14870 (16)	0.0518 (7)
H8A1	−0.2888	0.3447	0.1151	0.078*
H8A2	−0.2112	0.3864	0.1879	0.078*
H8A3	−0.1859	0.2586	0.1650	0.078*
Br1B	1.09635 (5)	0.88973 (3)	0.153281 (17)	0.06112 (12)
O1B	0.8026 (3)	1.13185 (16)	0.01304 (11)	0.0500 (5)
H1B	0.8822	1.1806	0.0214	0.075*
C1B	1.1100 (4)	0.8977 (2)	0.05449 (14)	0.0407 (6)
C2B	0.9897 (4)	0.9647 (2)	0.01929 (14)	0.0380 (6)
C3B	1.0055 (5)	0.9659 (3)	−0.05293 (15)	0.0493 (7)
H3B	0.9253	1.0111	−0.0796	0.059*
C4B	1.1372 (5)	0.9016 (3)	−0.08555 (18)	0.0623 (9)
H4B	1.1466	0.9031	−0.1345	0.075*
C5B	1.2543 (5)	0.8358 (3)	−0.0479 (2)	0.0618 (9)
H5B	1.3445	0.7924	−0.0709	0.074*
C6B	1.2412 (4)	0.8325 (3)	0.02258 (19)	0.0525 (8)
H6B	1.3206	0.7865	0.0490	0.063*
C7B	0.8394 (4)	1.0340 (2)	0.05289 (14)	0.0405 (6)
H7B	0.8787	1.0565	0.1004	0.049*
C8B	0.6624 (4)	0.9675 (3)	0.05759 (18)	0.0536 (8)
H8B1	0.5701	1.0119	0.0820	0.080*
H8B2	0.6844	0.8976	0.0828	0.080*
H8B3	0.6186	0.9501	0.0110	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1A	0.0939 (3)	0.04272 (17)	0.0756 (2)	−0.00522 (18)	0.0009 (2)	−0.01741 (16)
O1A	0.0535 (13)	0.0491 (11)	0.0457 (11)	−0.0190 (10)	0.0097 (9)	−0.0088 (9)
C1A	0.0491 (17)	0.0454 (15)	0.0431 (15)	−0.0093 (13)	0.0102 (13)	0.0011 (13)
C2A	0.0390 (14)	0.0387 (13)	0.0433 (15)	−0.0040 (12)	0.0092 (11)	0.0043 (11)
C3A	0.0552 (19)	0.0476 (18)	0.063 (2)	0.0002 (15)	−0.0012 (15)	0.0025 (14)
C4A	0.055 (2)	0.071 (2)	0.084 (2)	0.0115 (18)	0.0002 (19)	0.021 (2)
C5A	0.0398 (19)	0.095 (3)	0.068 (2)	−0.0068 (19)	−0.0046 (16)	0.023 (2)
C6A	0.050 (2)	0.079 (3)	0.0525 (18)	−0.0225 (19)	−0.0002 (14)	0.0029 (16)
C7A	0.0470 (16)	0.0328 (13)	0.0443 (15)	−0.0035 (12)	0.0025 (12)	0.0024 (11)
C8A	0.0457 (16)	0.0612 (19)	0.0484 (16)	0.0059 (14)	0.0041 (14)	0.0050 (15)
Br1B	0.0701 (2)	0.0615 (2)	0.05172 (18)	0.01563 (17)	−0.01687 (16)	0.00621 (14)
O1B	0.0485 (11)	0.0327 (10)	0.0688 (13)	−0.0017 (9)	−0.0228 (10)	0.0000 (9)
C1B	0.0397 (14)	0.0333 (13)	0.0492 (14)	−0.0042 (12)	−0.0054 (11)	0.0005 (11)
C2B	0.0382 (14)	0.0275 (12)	0.0483 (16)	−0.0059 (11)	−0.0018 (12)	−0.0021 (11)
C3B	0.0575 (19)	0.0418 (15)	0.0484 (17)	−0.0085 (15)	−0.0027 (14)	0.0026 (12)
C4B	0.074 (2)	0.056 (2)	0.0568 (18)	−0.0197 (19)	0.0196 (16)	−0.0120 (15)
C5B	0.057 (2)	0.0431 (17)	0.085 (3)	−0.0043 (17)	0.0241 (19)	−0.0118 (17)
C6B	0.0377 (16)	0.0399 (16)	0.080 (2)	0.0003 (13)	0.0012 (15)	−0.0017 (15)
C7B	0.0416 (15)	0.0359 (13)	0.0440 (15)	0.0019 (13)	−0.0105 (12)	0.0015 (11)
C8B	0.0430 (17)	0.0472 (16)	0.071 (2)	0.0004 (15)	0.0005 (15)	0.0032 (15)

Geometric parameters (Å, º) top

Br1A—C1A	1.909 (3)	Br1B—C1B	1.917 (3)
O1A—C7A	1.424 (3)	O1B—C7B	1.426 (3)
O1A—H1A	0.8400	O1B—H1B	0.8400
C1A—C2A	1.378 (4)	C1B—C2B	1.370 (4)
C1A—C6A	1.395 (4)	C1B—C6B	1.383 (4)
C2A—C3A	1.391 (4)	C2B—C3B	1.403 (4)
C2A—C7A	1.514 (4)	C2B—C7B	1.523 (4)
C3A—C4A	1.378 (5)	C3B—C4B	1.385 (5)
C3A—H3A	0.9500	C3B—H3B	0.9500
C4A—C5A	1.384 (6)	C4B—C5B	1.373 (5)
C4A—H4A	0.9500	C4B—H4B	0.9500
C5A—C6A	1.359 (6)	C5B—C6B	1.369 (5)
C5A—H5A	0.9500	C5B—H5B	0.9500
C6A—H6A	0.9500	C6B—H6B	0.9500
C7A—C8A	1.520 (4)	C7B—C8B	1.523 (4)
C7A—H7A	1.0000	C7B—H7B	1.0000
C8A—H8A1	0.9800	C8B—H8B1	0.9800
C8A—H8A2	0.9800	C8B—H8B2	0.9800
C8A—H8A3	0.9800	C8B—H8B3	0.9800

C7A—O1A—H1A	109.5	C7B—O1B—H1B	109.5
C2A—C1A—C6A	122.5 (3)	C2B—C1B—C6B	123.6 (3)
C2A—C1A—Br1A	120.5 (2)	C2B—C1B—Br1B	119.4 (2)
C6A—C1A—Br1A	117.0 (2)	C6B—C1B—Br1B	117.0 (2)
C1A—C2A—C3A	116.8 (3)	C1B—C2B—C3B	116.7 (3)
C1A—C2A—C7A	124.2 (3)	C1B—C2B—C7B	124.7 (3)
C3A—C2A—C7A	118.9 (3)	C3B—C2B—C7B	118.6 (3)
C4A—C3A—C2A	121.7 (3)	C4B—C3B—C2B	120.4 (3)
C4A—C3A—H3A	119.2	C4B—C3B—H3B	119.8
C2A—C3A—H3A	119.2	C2B—C3B—H3B	119.8
C3A—C4A—C5A	119.5 (4)	C5B—C4B—C3B	120.7 (3)
C3A—C4A—H4A	120.3	C5B—C4B—H4B	119.6
C5A—C4A—H4A	120.3	C3B—C4B—H4B	119.6
C6A—C5A—C4A	120.7 (3)	C6B—C5B—C4B	120.1 (3)
C6A—C5A—H5A	119.6	C6B—C5B—H5B	120.0
C4A—C5A—H5A	119.6	C4B—C5B—H5B	120.0
C5A—C6A—C1A	118.8 (3)	C5B—C6B—C1B	118.5 (3)
C5A—C6A—H6A	120.6	C5B—C6B—H6B	120.7
C1A—C6A—H6A	120.6	C1B—C6B—H6B	120.7
O1A—C7A—C2A	111.3 (2)	O1B—C7B—C8B	107.4 (2)
O1A—C7A—C8A	107.9 (2)	O1B—C7B—C2B	110.6 (2)
C2A—C7A—C8A	110.6 (2)	C8B—C7B—C2B	110.9 (2)
O1A—C7A—H7A	109.0	O1B—C7B—H7B	109.3
C2A—C7A—H7A	109.0	C8B—C7B—H7B	109.3
C8A—C7A—H7A	109.0	C2B—C7B—H7B	109.3
C7A—C8A—H8A1	109.5	C7B—C8B—H8B1	109.5
C7A—C8A—H8A2	109.5	C7B—C8B—H8B2	109.5
H8A1—C8A—H8A2	109.5	H8B1—C8B—H8B2	109.5
C7A—C8A—H8A3	109.5	C7B—C8B—H8B3	109.5
H8A1—C8A—H8A3	109.5	H8B1—C8B—H8B3	109.5
H8A2—C8A—H8A3	109.5	H8B2—C8B—H8B3	109.5

C6A—C1A—C2A—C3A	−0.4 (4)	C6B—C1B—C2B—C3B	−0.6 (4)
Br1A—C1A—C2A—C3A	179.8 (2)	Br1B—C1B—C2B—C3B	−179.3 (2)
C6A—C1A—C2A—C7A	177.3 (3)	C6B—C1B—C2B—C7B	177.6 (3)
Br1A—C1A—C2A—C7A	−2.5 (4)	Br1B—C1B—C2B—C7B	−1.1 (4)
C1A—C2A—C3A—C4A	0.7 (4)	C1B—C2B—C3B—C4B	0.1 (4)
C7A—C2A—C3A—C4A	−177.1 (3)	C7B—C2B—C3B—C4B	−178.2 (3)
C2A—C3A—C4A—C5A	−0.7 (5)	C2B—C3B—C4B—C5B	0.0 (5)
C3A—C4A—C5A—C6A	0.3 (6)	C3B—C4B—C5B—C6B	0.4 (5)
C4A—C5A—C6A—C1A	0.0 (5)	C4B—C5B—C6B—C1B	−0.8 (5)
C2A—C1A—C6A—C5A	0.0 (5)	C2B—C1B—C6B—C5B	1.0 (4)
Br1A—C1A—C6A—C5A	179.8 (3)	Br1B—C1B—C6B—C5B	179.7 (2)
C1A—C2A—C7A—O1A	145.5 (3)	C1B—C2B—C7B—O1B	150.2 (2)
C3A—C2A—C7A—O1A	−36.9 (3)	C3B—C2B—C7B—O1B	−31.6 (3)
C1A—C2A—C7A—C8A	−94.5 (3)	C1B—C2B—C7B—C8B	−90.7 (3)
C3A—C2A—C7A—C8A	83.1 (3)	C3B—C2B—C7B—C8B	87.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O1Bⁱ	0.84	1.81	2.645 (3)	177
O1B—H1B···O1Aⁱⁱ	0.84	1.81	2.627 (3)	165

Symmetry codes: (i) x−1/2, −y+3/2, −z; (ii) x+1, y+1, z.

Experimental details

Crystal data
Chemical formula	C₈H₉BrO
M_r	201.06
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	193
a, b, c (Å)	7.3235 (6), 11.9440 (11), 19.3583 (18)
V (Å³)	1693.3 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	4.79
Crystal size (mm)	0.20 × 0.08 × 0.08

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1998)
T_min, T_max	0.434, 0.680
No. of measured, independent and observed [I > 2σ(I)] reflections	12365, 4195, 3420
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.080, 1.03
No. of reflections	4195
No. of parameters	185
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.67, −0.33
Absolute structure	Flack, 1983, 1788 Friedel pairs
Absolute structure parameter	−0.004 (10)

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2000).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O1Bⁱ	0.84	1.81	2.645 (3)	176.8
O1B—H1B···O1Aⁱⁱ	0.84	1.81	2.627 (3)	165.4

Symmetry codes: (i) x−1/2, −y+3/2, −z; (ii) x+1, y+1, z.

Footnotes

‡Current address: Michigan State University, Department of Chemistry, East Lansing, MI 48824, USA.

Acknowledgements

The CCD-based X-ray diffractometer at Harvard University was purchased through an NIH grant (1S10RR11937–01).

References

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