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ISSN: 2056-9890

(S)-(+)-1-(2-Bromo­phen­yl)ethanol

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[Angiolini, D., Geppi, M., Marchetti, F., Ruggeri, G. & Veracini, C. A. (1995). Gazz. Chim. Ital. 125, 17-22.]); Venkatachalam et al. (2005[Venkatachalam, T. K., Zheng, Y., Ghosh, S. & Uckun, F. M. (2005). J. Mol. Struct. 743, 103-115.]). For related literature, see: Staples (2001[Staples, R. J. (2001). Z. Kristallogr. New Cryst. Struct. 216 , 311-312.]); Staples & George (2005[Staples, R. J. & George, S. (2005). Z. Kristallogr. New Cryst. Struct. 220, 383-384.]); Staples & Huang (2002[Staples, R. J. & Huang, V. (2002). Z. Kristallogr. New Cryst. Struct. 217, 554-555.]).

[Scheme 1]

Experimental

Crystal data
  • C8H9BrO

  • Mr = 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[Sheldrick, G. M. (1998). SADABS. University of Göttingen, Germany.]) Tmin = 0.434, Tmax = 0.680

  • 12365 measured reflections

  • 4195 independent reflections

  • 3420 reflections with I > 2σ(I)

  • Rint = 0.027

Refinement
  • R[F2 > 2σ(F2)] = 0.033

  • wR(F2) = 0.080

  • S = 1.03

  • 4195 reflections

  • 185 parameters

  • H-atom parameters constrained

  • Δρmax = 0.67 e Å−3

  • Δρmin = −0.33 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), with 1788 Friedel pairs

  • Flack parameter: −0.004 (10)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (1997). SMART. Version 5.054. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2003[Bruker (2003). SAINT. Version 6.25. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: SHELXTL (Bruker, 2000[Bruker (2000). SHELXTL. Version 6.14. Bruker AXS Inc., Madison, Wisconsin, USA.]); software used to prepare material for publication: SHELXTL.

Supporting information


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.

Refinement top

All H atoms were found by difference Fourier methods and refined isotropically.

Structure description 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].

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
[Figure 1] Fig. 1. Thermal ellipsoid plot (50% probability) of the title compound.
[Figure 2] Fig. 2. Packing diagram of the title compund showing the linear hydrogen bonding interaction.
(S)-(+)-1-(2-Bromophenyl)ethanol top
Crystal data top
C8H9BrOF(000) = 800
Mr = 201.06Dx = 1.577 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 3839 reflections
a = 7.3235 (6) Åθ = 3.0–23.9°
b = 11.9440 (11) ŵ = 4.79 mm1
c = 19.3583 (18) ÅT = 193 K
V = 1693.3 (3) Å3Needle, white
Z = 80.20 × 0.08 × 0.08 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
4195 independent reflections
Radiation source: normal-focus sealed tube3420 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
phi and ω scansθmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1998)
h = 79
Tmin = 0.434, Tmax = 0.680k = 1512
12365 measured reflectionsl = 2521
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033H-atom parameters constrained
wR(F2) = 0.080 w = 1/[σ2(Fo2) + (0.0359P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
4195 reflectionsΔρmax = 0.67 e Å3
185 parametersΔρmin = 0.33 e Å3
0 restraintsAbsolute structure: Flack, 1983, 1788 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.004 (10)
Crystal data top
C8H9BrOV = 1693.3 (3) Å3
Mr = 201.06Z = 8
Orthorhombic, P212121Mo Kα radiation
a = 7.3235 (6) ŵ = 4.79 mm1
b = 11.9440 (11) ÅT = 193 K
c = 19.3583 (18) Å0.20 × 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)
Tmin = 0.434, Tmax = 0.680Rint = 0.027
12365 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.033H-atom parameters constrained
wR(F2) = 0.080Δρmax = 0.67 e Å3
S = 1.03Δρmin = 0.33 e Å3
4195 reflectionsAbsolute structure: Flack, 1983, 1788 Friedel pairs
185 parametersAbsolute 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
xyzUiso*/Ueq
Br1A0.13612 (6)0.57908 (3)0.20047 (2)0.07072 (14)
O1A0.0096 (3)0.29862 (17)0.05433 (10)0.0494 (5)
H1A0.10350.31820.03260.074*
C1A0.2226 (4)0.4285 (2)0.20561 (15)0.0458 (7)
C2A0.1479 (4)0.3466 (2)0.16427 (14)0.0403 (6)
C3A0.2190 (5)0.2392 (3)0.17111 (16)0.0553 (8)
H3A0.17180.18070.14310.066*
C4A0.3564 (5)0.2154 (4)0.2175 (2)0.0701 (10)
H4A0.40200.14130.22170.084*
C5A0.4272 (5)0.3004 (4)0.25806 (19)0.0675 (10)
H5A0.52220.28430.29000.081*
C6A0.3622 (4)0.4066 (3)0.25272 (17)0.0606 (9)
H6A0.41100.46490.28060.073*
C7A0.0089 (4)0.3657 (2)0.11472 (14)0.0414 (6)
H7A0.01100.44640.10100.050*
C8A0.1898 (4)0.3363 (3)0.14870 (16)0.0518 (7)
H8A10.28880.34470.11510.078*
H8A20.21120.38640.18790.078*
H8A30.18590.25860.16500.078*
Br1B1.09635 (5)0.88973 (3)0.153281 (17)0.06112 (12)
O1B0.8026 (3)1.13185 (16)0.01304 (11)0.0500 (5)
H1B0.88221.18060.02140.075*
C1B1.1100 (4)0.8977 (2)0.05449 (14)0.0407 (6)
C2B0.9897 (4)0.9647 (2)0.01929 (14)0.0380 (6)
C3B1.0055 (5)0.9659 (3)0.05293 (15)0.0493 (7)
H3B0.92531.01110.07960.059*
C4B1.1372 (5)0.9016 (3)0.08555 (18)0.0623 (9)
H4B1.14660.90310.13450.075*
C5B1.2543 (5)0.8358 (3)0.0479 (2)0.0618 (9)
H5B1.34450.79240.07090.074*
C6B1.2412 (4)0.8325 (3)0.02258 (19)0.0525 (8)
H6B1.32060.78650.04900.063*
C7B0.8394 (4)1.0340 (2)0.05289 (14)0.0405 (6)
H7B0.87871.05650.10040.049*
C8B0.6624 (4)0.9675 (3)0.05759 (18)0.0536 (8)
H8B10.57011.01190.08200.080*
H8B20.68440.89760.08280.080*
H8B30.61860.95010.01100.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br1A0.0939 (3)0.04272 (17)0.0756 (2)0.00522 (18)0.0009 (2)0.01741 (16)
O1A0.0535 (13)0.0491 (11)0.0457 (11)0.0190 (10)0.0097 (9)0.0088 (9)
C1A0.0491 (17)0.0454 (15)0.0431 (15)0.0093 (13)0.0102 (13)0.0011 (13)
C2A0.0390 (14)0.0387 (13)0.0433 (15)0.0040 (12)0.0092 (11)0.0043 (11)
C3A0.0552 (19)0.0476 (18)0.063 (2)0.0002 (15)0.0012 (15)0.0025 (14)
C4A0.055 (2)0.071 (2)0.084 (2)0.0115 (18)0.0002 (19)0.021 (2)
C5A0.0398 (19)0.095 (3)0.068 (2)0.0068 (19)0.0046 (16)0.023 (2)
C6A0.050 (2)0.079 (3)0.0525 (18)0.0225 (19)0.0002 (14)0.0029 (16)
C7A0.0470 (16)0.0328 (13)0.0443 (15)0.0035 (12)0.0025 (12)0.0024 (11)
C8A0.0457 (16)0.0612 (19)0.0484 (16)0.0059 (14)0.0041 (14)0.0050 (15)
Br1B0.0701 (2)0.0615 (2)0.05172 (18)0.01563 (17)0.01687 (16)0.00621 (14)
O1B0.0485 (11)0.0327 (10)0.0688 (13)0.0017 (9)0.0228 (10)0.0000 (9)
C1B0.0397 (14)0.0333 (13)0.0492 (14)0.0042 (12)0.0054 (11)0.0005 (11)
C2B0.0382 (14)0.0275 (12)0.0483 (16)0.0059 (11)0.0018 (12)0.0021 (11)
C3B0.0575 (19)0.0418 (15)0.0484 (17)0.0085 (15)0.0027 (14)0.0026 (12)
C4B0.074 (2)0.056 (2)0.0568 (18)0.0197 (19)0.0196 (16)0.0120 (15)
C5B0.057 (2)0.0431 (17)0.085 (3)0.0043 (17)0.0241 (19)0.0118 (17)
C6B0.0377 (16)0.0399 (16)0.080 (2)0.0003 (13)0.0012 (15)0.0017 (15)
C7B0.0416 (15)0.0359 (13)0.0440 (15)0.0019 (13)0.0105 (12)0.0015 (11)
C8B0.0430 (17)0.0472 (16)0.071 (2)0.0004 (15)0.0005 (15)0.0032 (15)
Geometric parameters (Å, º) top
Br1A—C1A1.909 (3)Br1B—C1B1.917 (3)
O1A—C7A1.424 (3)O1B—C7B1.426 (3)
O1A—H1A0.8400O1B—H1B0.8400
C1A—C2A1.378 (4)C1B—C2B1.370 (4)
C1A—C6A1.395 (4)C1B—C6B1.383 (4)
C2A—C3A1.391 (4)C2B—C3B1.403 (4)
C2A—C7A1.514 (4)C2B—C7B1.523 (4)
C3A—C4A1.378 (5)C3B—C4B1.385 (5)
C3A—H3A0.9500C3B—H3B0.9500
C4A—C5A1.384 (6)C4B—C5B1.373 (5)
C4A—H4A0.9500C4B—H4B0.9500
C5A—C6A1.359 (6)C5B—C6B1.369 (5)
C5A—H5A0.9500C5B—H5B0.9500
C6A—H6A0.9500C6B—H6B0.9500
C7A—C8A1.520 (4)C7B—C8B1.523 (4)
C7A—H7A1.0000C7B—H7B1.0000
C8A—H8A10.9800C8B—H8B10.9800
C8A—H8A20.9800C8B—H8B20.9800
C8A—H8A30.9800C8B—H8B30.9800
C7A—O1A—H1A109.5C7B—O1B—H1B109.5
C2A—C1A—C6A122.5 (3)C2B—C1B—C6B123.6 (3)
C2A—C1A—Br1A120.5 (2)C2B—C1B—Br1B119.4 (2)
C6A—C1A—Br1A117.0 (2)C6B—C1B—Br1B117.0 (2)
C1A—C2A—C3A116.8 (3)C1B—C2B—C3B116.7 (3)
C1A—C2A—C7A124.2 (3)C1B—C2B—C7B124.7 (3)
C3A—C2A—C7A118.9 (3)C3B—C2B—C7B118.6 (3)
C4A—C3A—C2A121.7 (3)C4B—C3B—C2B120.4 (3)
C4A—C3A—H3A119.2C4B—C3B—H3B119.8
C2A—C3A—H3A119.2C2B—C3B—H3B119.8
C3A—C4A—C5A119.5 (4)C5B—C4B—C3B120.7 (3)
C3A—C4A—H4A120.3C5B—C4B—H4B119.6
C5A—C4A—H4A120.3C3B—C4B—H4B119.6
C6A—C5A—C4A120.7 (3)C6B—C5B—C4B120.1 (3)
C6A—C5A—H5A119.6C6B—C5B—H5B120.0
C4A—C5A—H5A119.6C4B—C5B—H5B120.0
C5A—C6A—C1A118.8 (3)C5B—C6B—C1B118.5 (3)
C5A—C6A—H6A120.6C5B—C6B—H6B120.7
C1A—C6A—H6A120.6C1B—C6B—H6B120.7
O1A—C7A—C2A111.3 (2)O1B—C7B—C8B107.4 (2)
O1A—C7A—C8A107.9 (2)O1B—C7B—C2B110.6 (2)
C2A—C7A—C8A110.6 (2)C8B—C7B—C2B110.9 (2)
O1A—C7A—H7A109.0O1B—C7B—H7B109.3
C2A—C7A—H7A109.0C8B—C7B—H7B109.3
C8A—C7A—H7A109.0C2B—C7B—H7B109.3
C7A—C8A—H8A1109.5C7B—C8B—H8B1109.5
C7A—C8A—H8A2109.5C7B—C8B—H8B2109.5
H8A1—C8A—H8A2109.5H8B1—C8B—H8B2109.5
C7A—C8A—H8A3109.5C7B—C8B—H8B3109.5
H8A1—C8A—H8A3109.5H8B1—C8B—H8B3109.5
H8A2—C8A—H8A3109.5H8B2—C8B—H8B3109.5
C6A—C1A—C2A—C3A0.4 (4)C6B—C1B—C2B—C3B0.6 (4)
Br1A—C1A—C2A—C3A179.8 (2)Br1B—C1B—C2B—C3B179.3 (2)
C6A—C1A—C2A—C7A177.3 (3)C6B—C1B—C2B—C7B177.6 (3)
Br1A—C1A—C2A—C7A2.5 (4)Br1B—C1B—C2B—C7B1.1 (4)
C1A—C2A—C3A—C4A0.7 (4)C1B—C2B—C3B—C4B0.1 (4)
C7A—C2A—C3A—C4A177.1 (3)C7B—C2B—C3B—C4B178.2 (3)
C2A—C3A—C4A—C5A0.7 (5)C2B—C3B—C4B—C5B0.0 (5)
C3A—C4A—C5A—C6A0.3 (6)C3B—C4B—C5B—C6B0.4 (5)
C4A—C5A—C6A—C1A0.0 (5)C4B—C5B—C6B—C1B0.8 (5)
C2A—C1A—C6A—C5A0.0 (5)C2B—C1B—C6B—C5B1.0 (4)
Br1A—C1A—C6A—C5A179.8 (3)Br1B—C1B—C6B—C5B179.7 (2)
C1A—C2A—C7A—O1A145.5 (3)C1B—C2B—C7B—O1B150.2 (2)
C3A—C2A—C7A—O1A36.9 (3)C3B—C2B—C7B—O1B31.6 (3)
C1A—C2A—C7A—C8A94.5 (3)C1B—C2B—C7B—C8B90.7 (3)
C3A—C2A—C7A—C8A83.1 (3)C3B—C2B—C7B—C8B87.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1A···O1Bi0.841.812.645 (3)177
O1B—H1B···O1Aii0.841.812.627 (3)165
Symmetry codes: (i) x1/2, y+3/2, z; (ii) x+1, y+1, z.

Experimental details

Crystal data
Chemical formulaC8H9BrO
Mr201.06
Crystal system, space groupOrthorhombic, P212121
Temperature (K)193
a, b, c (Å)7.3235 (6), 11.9440 (11), 19.3583 (18)
V3)1693.3 (3)
Z8
Radiation typeMo Kα
µ (mm1)4.79
Crystal size (mm)0.20 × 0.08 × 0.08
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1998)
Tmin, Tmax0.434, 0.680
No. of measured, independent and
observed [I > 2σ(I)] reflections
12365, 4195, 3420
Rint0.027
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.080, 1.03
No. of reflections4195
No. of parameters185
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.67, 0.33
Absolute structureFlack, 1983, 1788 Friedel pairs
Absolute structure parameter0.004 (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···AD—HH···AD···AD—H···A
O1A—H1A···O1Bi0.841.812.645 (3)176.8
O1B—H1B···O1Aii0.841.812.627 (3)165.4
Symmetry codes: (i) x1/2, 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).

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