organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

3-(2-Bromo­acet­yl)phenyl benzoate

aDepartment of Chemistry, Karnatak University's Karnatak Science College, Dharwad, Karnataka 580 001, India, bDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India, and cDepartment of Physics, AVK College for Women, Hassan 573 201, Karnataka, India
*Correspondence e-mail: devarajegowda@yahoo.com

(Received 24 January 2013; accepted 28 January 2013; online 2 February 2013)

In the title compound, C15H11BrO3, the dihedral angle between the benzene rings is 72.59 (6)°. In the crystal, pairs of C—H⋯π contacts form inversion dimers. Additional C—H⋯O hydrogen bonds generate R21(6) ring motifs and stack these dimers along the b axis. Short inter­molecular Br⋯O contacts of 3.254 (3) Å are also observed and link the stacks into a three-dimensional network.

Related literature

For the biological applications and synthesis of the title compound, see: Naoto et al. (2008[Naoto, O., Mariko, O., Takashi, S., Satoshi, K., Atsuko, M., Noriaki, U., Yoshisuke, N., Keishi, K., Masamori, S. & Yushi, K. (2008). PCT Int. Appl. WO 2008029825/A1 20080313.]); Shwu-Jiuan & Mei-Hua (1984[Shwu-Jiuan, L. & Mei-Hua, L. (1984). Bull. Inst. Chem. Acad. Sin. 31, 55-58.]); Jaakko & Erkki (1959[Jaakko, H. & Erkki, H. (1959). Acta Chem. Scand. 13, 329-33.]); Junichi et al. (1956[Junichi, I., Takuro, I., Chikara, K. & Mitsutaka, K. (1956). Ann. Rept. G. Tanabe Co. Ltd, 1, 17-20.]); D'Amico et al. (1956[D'Amico, A., Bertolini, L. & Monreale, C. (1956). Chim. l'Ind. (Milan, Italy), 38, 93-99.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.])

[Scheme 1]

Experimental

Crystal data
  • C15H11BrO3

  • Mr = 319.15

  • Monoclinic, P 21 /n

  • a = 12.5055 (4) Å

  • b = 5.4409 (2) Å

  • c = 19.5178 (6) Å

  • β = 90.859 (2)°

  • V = 1327.86 (8) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 3.10 mm−1

  • T = 296 K

  • 0.24 × 0.20 × 0.12 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2007[Sheldrick, G. M. (2007). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.770, Tmax = 1.000

  • 11209 measured reflections

  • 2344 independent reflections

  • 1929 reflections with I > 2σ(I)

  • Rint = 0.033

Refinement
  • R[F2 > 2σ(F2)] = 0.033

  • wR(F2) = 0.092

  • S = 1.05

  • 2344 reflections

  • 172 parameters

  • H-atom parameters constrained

  • Δρmax = 0.37 e Å−3

  • Δρmin = −0.62 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C10–C15 benzene ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C4—H4⋯O3i 0.93 2.70 3.557 (4) 153
C1—H1B⋯O3i 0.97 2.65 3.550 (4) 155
C6—H6⋯Cg2ii 0.93 2.88 3.627 (3) 138
Symmetry codes: (i) x, y-1, z; (ii) -x+1, -y+1, -z.

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

3-(2-bromoacetyl)phenyl benzoate is key starting material for the synthesis of phenylephrine, (R)-3-[-1-hydroxy-2-(methylamino)ethyl]phenol. Phenylephrine is a selective α1-adrenergic receptor agonist used primarily as a decongestant, as an agent to dilate the pupils, and to increase blood pressure.

Oral phenylephrine is extensively metabolized by monoamine oxidase (Naoto et al., 2008), an enzyme that is present in the gastrointestinal tract and in the liver. Therefore, compared to intravenous pseudoephedrine, it has a reduced and variable bioavailability, only up to 38% (Shwu-Jiuan & Mei-Hua, 1984; Jaakko & Erkki, 1959). Because phenylephrine is a directly selective α-adrenergic receptor agonist, it does not cause the release of endogenous noradrenaline, as pseudoephedrine does. Therefore, phenylephrine is less likely to cause side effects such as central nervous system stimulation, insomnia, anxiety, irritability, and restlessness (Junichi et al., 1956). Phenylephrine's effectiveness as a decongestant stems from its vasoconstriction of nasal blood vessels, thereby decreasing blood flow to the sinusoidal vessels, leading to decreased mucosal edema (D'Amico et al., 1956).

The asymmetric unit of 3-(2-bromoacetylphenyl benzoate is shown in Fig. 1. The dihedral angle between two (C3–C8) and (C10—C15) benzene rings is 72.59 (6)°. In the crystal structure a pair of C6—H6···π [Cg(2)(C10–C15) contacts form inversion dimers. Additional C4—H4···O3 and C1—H1B···O3 (Table.1) hydrogen bonds generate R12(6) ring motifs (Bernstein et al., 1995) and stack these dimers along the b axis (Fig. 2). Short intermolecular Br1···O2 contacts, 3.254 (3) Å are also observed and link the stacks into a three dimensional network.

Related literature top

For the biological applications and synthesis of the title compound, see: Naoto et al. (2008); Shwu-Jiuan & Mei-Hua (1984); Jaakko & Erkki (1959); Junichi et al. (1956); D'Amico et al. (1956). For hydrogen-bond motifs, see: Bernstein et al. (1995)

Experimental top

All the chemicals used were of analytical reagent grade and were used directly without further purification. The title compound was synthesized according to an already reported method (Shwu-Jiuan & Mei-Hua, 1984). The crude product was recrystallized from an ethanol/chloroform mixture, to give colourless crystals in 78% yield.

Refinement top

All H atoms were positioned geometrically, with C—H = 0.93 Å for aromatic H and C—H = 0.97 Å for methylene H and refined using a riding model with Uiso(H) = 1.2Ueq(C) for aromatic and methylene H.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are shown as spheres of arbitrary radius.
[Figure 2] Fig. 2. Crystal packing along b axis for the title compound with hydrogen bonds drawn as dashed lines.
3-(2-Bromoacetyl)phenyl benzoate top
Crystal data top
C15H11BrO3F(000) = 640
Mr = 319.15Dx = 1.596 Mg m3
Monoclinic, P21/nMelting point: 378 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 12.5055 (4) ÅCell parameters from 2344 reflections
b = 5.4409 (2) Åθ = 1.9–25.0°
c = 19.5178 (6) ŵ = 3.10 mm1
β = 90.859 (2)°T = 296 K
V = 1327.86 (8) Å3Plate, colourless
Z = 40.24 × 0.20 × 0.12 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2344 independent reflections
Radiation source: fine-focus sealed tube1929 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
ω and ϕ scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2007)
h = 1414
Tmin = 0.770, Tmax = 1.000k = 66
11209 measured reflectionsl = 2323
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0489P)2 + 0.8292P]
where P = (Fo2 + 2Fc2)/3
2344 reflections(Δ/σ)max = 0.001
172 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.62 e Å3
Crystal data top
C15H11BrO3V = 1327.86 (8) Å3
Mr = 319.15Z = 4
Monoclinic, P21/nMo Kα radiation
a = 12.5055 (4) ŵ = 3.10 mm1
b = 5.4409 (2) ÅT = 296 K
c = 19.5178 (6) Å0.24 × 0.20 × 0.12 mm
β = 90.859 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
2344 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2007)
1929 reflections with I > 2σ(I)
Tmin = 0.770, Tmax = 1.000Rint = 0.033
11209 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0330 restraints
wR(F2) = 0.092H-atom parameters constrained
S = 1.05Δρmax = 0.37 e Å3
2344 reflectionsΔρmin = 0.62 e Å3
172 parameters
Special details top

Experimental. 3-(Bromo acetyl) phenyl benzoate: it was obtained as an off-white solid; M.P: 378k; GCMS data m/e 320 1H NMR (300 MHz, CDCl3, δ, p.p.m.): 4.46 (s 2H, Methylene-CH2),7.50 (s,1H, Ar—H), 7.52 (s,1H, Ar—H), 7.66 (s,1H, Ar—H), 7.68 (s,1H, Ar—H), 7.88 (s,1H, Ar—H), 7.90 (s,1H, Ar—H), 8.19 (d,2H, Ar—H),

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Br10.93093 (3)0.55127 (7)0.763352 (16)0.05813 (16)
O10.57395 (15)0.2166 (4)0.92902 (10)0.0458 (5)
O21.00505 (17)0.2020 (5)0.87494 (14)0.0697 (7)
O30.5845 (2)0.5101 (5)0.84970 (16)0.0724 (8)
C10.8494 (2)0.3090 (7)0.81046 (16)0.0524 (8)
H1A0.82100.19280.77720.063*
H1B0.78930.38910.83190.063*
C20.9115 (2)0.1696 (6)0.86438 (15)0.0410 (7)
C30.8497 (2)0.0154 (5)0.90374 (14)0.0371 (7)
C40.7386 (2)0.0330 (6)0.89847 (14)0.0378 (6)
H40.70020.07660.87100.045*
C50.6866 (2)0.2118 (6)0.93378 (14)0.0396 (7)
C60.7396 (3)0.3758 (6)0.97553 (16)0.0489 (8)
H60.70250.49650.99910.059*
C70.8502 (3)0.3567 (7)0.98166 (16)0.0519 (8)
H70.88780.46471.01000.062*
C80.9040 (2)0.1796 (6)0.94613 (14)0.0438 (7)
H80.97800.16930.95050.053*
C90.5314 (2)0.3695 (6)0.88120 (16)0.0430 (7)
C100.4140 (2)0.3355 (6)0.87324 (15)0.0392 (7)
C110.3575 (3)0.5030 (6)0.83355 (19)0.0564 (9)
H110.39290.63270.81270.068*
C120.2485 (3)0.4773 (7)0.8249 (2)0.0626 (10)
H120.21020.59220.79920.075*
C130.1965 (3)0.2843 (7)0.85389 (17)0.0553 (9)
H130.12310.26640.84730.066*
C140.2517 (3)0.1179 (7)0.89246 (18)0.0546 (9)
H140.21580.01370.91200.066*
C150.3611 (2)0.1427 (6)0.90285 (16)0.0476 (7)
H150.39840.02940.92970.057*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0559 (2)0.0682 (3)0.0502 (2)0.01670 (17)0.00215 (15)0.00925 (17)
O10.0314 (10)0.0549 (13)0.0512 (12)0.0049 (10)0.0054 (9)0.0110 (10)
O20.0332 (13)0.0820 (19)0.0935 (18)0.0101 (12)0.0161 (11)0.0277 (15)
O30.0443 (13)0.0693 (17)0.103 (2)0.0134 (12)0.0088 (13)0.0430 (16)
C10.0366 (16)0.069 (2)0.0517 (17)0.0138 (16)0.0050 (13)0.0151 (17)
C20.0282 (15)0.0483 (18)0.0463 (16)0.0014 (13)0.0045 (12)0.0000 (15)
C30.0308 (14)0.0420 (17)0.0384 (15)0.0019 (12)0.0043 (12)0.0032 (12)
C40.0319 (14)0.0423 (16)0.0391 (15)0.0034 (13)0.0045 (12)0.0002 (13)
C50.0318 (14)0.0472 (18)0.0400 (15)0.0001 (13)0.0014 (12)0.0079 (14)
C60.055 (2)0.0480 (18)0.0440 (17)0.0006 (16)0.0034 (14)0.0049 (15)
C70.054 (2)0.055 (2)0.0466 (17)0.0136 (17)0.0107 (14)0.0067 (16)
C80.0349 (15)0.0523 (19)0.0440 (16)0.0076 (14)0.0085 (13)0.0005 (15)
C90.0398 (16)0.0384 (16)0.0510 (17)0.0032 (14)0.0036 (14)0.0030 (15)
C100.0353 (15)0.0350 (16)0.0474 (16)0.0028 (13)0.0029 (12)0.0009 (14)
C110.0446 (18)0.054 (2)0.071 (2)0.0005 (16)0.0005 (16)0.0201 (18)
C120.049 (2)0.067 (2)0.071 (2)0.0112 (18)0.0079 (17)0.0168 (19)
C130.0350 (16)0.067 (2)0.064 (2)0.0000 (16)0.0008 (15)0.0002 (19)
C140.0405 (18)0.054 (2)0.069 (2)0.0080 (16)0.0076 (15)0.0077 (18)
C150.0416 (17)0.0445 (18)0.0568 (18)0.0030 (15)0.0028 (14)0.0060 (16)
Geometric parameters (Å, º) top
Br1—C11.910 (3)C7—C81.370 (5)
O1—C91.353 (4)C7—H70.9300
O1—C51.411 (3)C8—H80.9300
O2—C21.198 (3)C9—C101.485 (4)
O3—C91.191 (4)C10—C151.372 (4)
C1—C21.503 (4)C10—C111.384 (4)
C1—H1A0.9700C11—C121.378 (5)
C1—H1B0.9700C11—H110.9300
C2—C31.489 (4)C12—C131.362 (5)
C3—C81.388 (4)C12—H120.9300
C3—C41.395 (4)C13—C141.359 (5)
C4—C51.363 (4)C13—H130.9300
C4—H40.9300C14—C151.387 (4)
C5—C61.372 (4)C14—H140.9300
C6—C71.390 (4)C15—H150.9300
C6—H60.9300
C9—O1—C5116.0 (2)C7—C8—C3121.0 (3)
C2—C1—Br1114.3 (2)C7—C8—H8119.5
C2—C1—H1A108.7C3—C8—H8119.5
Br1—C1—H1A108.7O3—C9—O1122.3 (3)
C2—C1—H1B108.7O3—C9—C10125.8 (3)
Br1—C1—H1B108.7O1—C9—C10111.9 (3)
H1A—C1—H1B107.6C15—C10—C11119.6 (3)
O2—C2—C3121.6 (3)C15—C10—C9122.2 (3)
O2—C2—C1122.6 (3)C11—C10—C9118.2 (3)
C3—C2—C1115.8 (2)C12—C11—C10119.8 (3)
C8—C3—C4118.5 (3)C12—C11—H11120.1
C8—C3—C2119.3 (3)C10—C11—H11120.1
C4—C3—C2122.2 (3)C13—C12—C11120.4 (3)
C5—C4—C3119.6 (3)C13—C12—H12119.8
C5—C4—H4120.2C11—C12—H12119.8
C3—C4—H4120.2C14—C13—C12120.1 (3)
C4—C5—C6122.4 (3)C14—C13—H13120.0
C4—C5—O1117.6 (3)C12—C13—H13120.0
C6—C5—O1120.0 (3)C13—C14—C15120.5 (3)
C5—C6—C7118.3 (3)C13—C14—H14119.7
C5—C6—H6120.9C15—C14—H14119.7
C7—C6—H6120.9C10—C15—C14119.6 (3)
C8—C7—C6120.3 (3)C10—C15—H15120.2
C8—C7—H7119.8C14—C15—H15120.2
C6—C7—H7119.8
Br1—C1—C2—O22.7 (5)C4—C3—C8—C70.6 (4)
Br1—C1—C2—C3178.1 (2)C2—C3—C8—C7178.2 (3)
O2—C2—C3—C89.9 (5)C5—O1—C9—O37.3 (5)
C1—C2—C3—C8169.3 (3)C5—O1—C9—C10171.8 (2)
O2—C2—C3—C4171.4 (3)O3—C9—C10—C15168.8 (3)
C1—C2—C3—C49.4 (4)O1—C9—C10—C1510.3 (4)
C8—C3—C4—C51.1 (4)O3—C9—C10—C1110.1 (5)
C2—C3—C4—C5177.6 (3)O1—C9—C10—C11170.8 (3)
C3—C4—C5—C60.8 (4)C15—C10—C11—C121.0 (5)
C3—C4—C5—O1177.6 (2)C9—C10—C11—C12179.9 (3)
C9—O1—C5—C495.2 (3)C10—C11—C12—C131.6 (6)
C9—O1—C5—C687.9 (3)C11—C12—C13—C141.1 (6)
C4—C5—C6—C70.1 (5)C12—C13—C14—C150.1 (6)
O1—C5—C6—C7176.6 (3)C11—C10—C15—C140.2 (5)
C5—C6—C7—C80.7 (5)C9—C10—C15—C14178.7 (3)
C6—C7—C8—C30.3 (5)C13—C14—C15—C100.7 (5)
Hydrogen-bond geometry (Å, º) top
Cg2 is the centroid of the C10–C15 benzene ring.
D—H···AD—HH···AD···AD—H···A
C4—H4···O3i0.932.703.557 (4)153
C1—H1B···O3i0.972.653.550 (4)155
C6—H6···Cg2ii0.932.883.627 (3)138
Symmetry codes: (i) x, y1, z; (ii) x+1, y+1, z.

Experimental details

Crystal data
Chemical formulaC15H11BrO3
Mr319.15
Crystal system, space groupMonoclinic, P21/n
Temperature (K)296
a, b, c (Å)12.5055 (4), 5.4409 (2), 19.5178 (6)
β (°) 90.859 (2)
V3)1327.86 (8)
Z4
Radiation typeMo Kα
µ (mm1)3.10
Crystal size (mm)0.24 × 0.20 × 0.12
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2007)
Tmin, Tmax0.770, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
11209, 2344, 1929
Rint0.033
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.092, 1.05
No. of reflections2344
No. of parameters172
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.37, 0.62

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top
Cg2 is the centroid of the C10–C15 benzene ring.
D—H···AD—HH···AD···AD—H···A
C4—H4···O3i0.932.7023.557 (4)153
C1—H1B···O3i0.972.6463.550 (4)155
C6—H6···Cg2ii0.932.883.627 (3)138
Symmetry codes: (i) x, y1, z; (ii) x+1, y+1, z.
 

Acknowledgements

The authors thank the Universities Sophisticated Instrumental Centre, Karnatak University, Dharwad, for the X-ray data collection and GCMS, IR, CHNS and NMR data. SPA is grateful to Karnatak Science College, Dharwad, for providing laboratory facilities.

References

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First citationNaoto, O., Mariko, O., Takashi, S., Satoshi, K., Atsuko, M., Noriaki, U., Yoshisuke, N., Keishi, K., Masamori, S. & Yushi, K. (2008). PCT Int. Appl. WO 2008029825/A1 20080313.
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First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationShwu-Jiuan, L. & Mei-Hua, L. (1984). Bull. Inst. Chem. Acad. Sin. 31, 55–58.

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