Literature DB >> 21754889

2-(4-Bromo-phen-yl)-2-oxoethyl 4-meth-oxy-benzoate.

Hoong-Kun Fun, Wan-Sin Loh, B Garudachari, Arun M Isloor, M N Satyanarayan.

Abstract

In the title compound, C(16)H(13)BrO(4), the benzene rings are almost perpendicular to each other, making a dihedral angle of 84.07 (8)°. In the crystal, the mol-ecules are linked into chains along the a axis via inter-molecular C-H⋯O hydrogen bonds. A C-H⋯π inter-action is also observed.

Entities: Chemical Disease Gene

Year: 2011 PMID： 21754889 PMCID： PMC3120282 DOI： 10.1107/S1600536811018988

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

Related literature

For background to and applications of phenacyl benzoates, see: Gandhi et al. (1995 ▶); Huang et al. (1996 ▶); Litera et al. (2006 ▶); Rather & Reid (1919 ▶); Ruzicka et al. (2002 ▶); Sheehan & Umezaw (1973 ▶). For the synthesis, see: Judefind & Reid (1920 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H13BrO4 M = 349.17 Triclinic, a = 7.9700 (5) Å b = 7.9852 (5) Å c = 11.3185 (7) Å α = 86.536 (1)° β = 83.205 (1)° γ = 89.633 (1)° V = 713.97 (8) Å3 Z = 2 Mo Kα radiation μ = 2.89 mm−1 T = 296 K 0.58 × 0.34 × 0.32 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.286, T max = 0.461 10671 measured reflections 3270 independent reflections 2767 reflections with I > 2σ(I) R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.027 wR(F 2) = 0.069 S = 1.05 3270 reflections 191 parameters H-atom parameters constrained Δρmax = 0.36 e Å−3 Δρmin = −0.52 e Å−3 Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811018988/is2716sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536811018988/is2716Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811018988/is2716Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₆H₁₃BrO₄	Z = 2
M_r = 349.17	F(000) = 352
Triclinic, P1	D_x = 1.624 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9700 (5) Å	Cell parameters from 4684 reflections
b = 7.9852 (5) Å	θ = 3.0–30.0°
c = 11.3185 (7) Å	µ = 2.89 mm⁻¹
α = 86.536 (1)°	T = 296 K
β = 83.205 (1)°	Block, colourless
γ = 89.633 (1)°	0.58 × 0.34 × 0.32 mm
V = 713.97 (8) Å³

Bruker SMART APEXII DUO CCD area-detector diffractometer	3270 independent reflections
Radiation source: fine-focus sealed tube	2767 reflections with I > 2σ(I)
graphite	R_int = 0.017
φ and ω scans	θ_max = 27.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
T_min = 0.286, T_max = 0.461	k = −10→10
10671 measured reflections	l = −14→14

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.069	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0314P)² + 0.2047P] where P = (F_o² + 2F_c²)/3
3270 reflections	(Δ/σ)_max = 0.001
191 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.52 e Å⁻³

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
Br1	0.26530 (3)	0.93852 (3)	0.738521 (19)	0.06416 (9)
O1	1.05611 (17)	0.7434 (2)	0.48016 (14)	0.0727 (4)
O2	1.07533 (16)	0.58534 (16)	0.28028 (12)	0.0543 (3)
O3	1.07066 (18)	0.84361 (18)	0.19107 (14)	0.0628 (4)
O4	1.82176 (17)	0.60709 (18)	0.03308 (13)	0.0589 (3)
C1	0.6023 (2)	0.7176 (2)	0.48878 (16)	0.0451 (4)
H1A	0.5962	0.6522	0.4242	0.054*
C2	0.4543 (2)	0.7690 (2)	0.55394 (16)	0.0471 (4)
H2A	0.3495	0.7382	0.5337	0.057*
C3	0.4655 (2)	0.8663 (2)	0.64896 (16)	0.0458 (4)
C4	0.6205 (3)	0.9145 (2)	0.67953 (17)	0.0521 (4)
H4A	0.6261	0.9816	0.7433	0.062*
C5	0.7661 (2)	0.8622 (2)	0.61464 (17)	0.0502 (4)
H5A	0.8705	0.8939	0.6351	0.060*
C6	0.7594 (2)	0.7624 (2)	0.51864 (15)	0.0426 (4)
C7	0.9203 (2)	0.7110 (2)	0.44998 (17)	0.0483 (4)
C8	0.9105 (2)	0.6156 (3)	0.33964 (18)	0.0517 (4)
H8A	0.8535	0.5094	0.3618	0.062*
H8B	0.8449	0.6796	0.2858	0.062*
C9	1.1450 (2)	0.7150 (2)	0.21027 (16)	0.0462 (4)
C10	1.3205 (2)	0.6803 (2)	0.16089 (15)	0.0413 (4)
C11	1.4168 (2)	0.5522 (2)	0.20810 (16)	0.0443 (4)
H11A	1.3686	0.4808	0.2708	0.053*
C12	1.5823 (2)	0.5308 (2)	0.16269 (17)	0.0464 (4)
H12A	1.6453	0.4447	0.1946	0.056*
C13	1.6566 (2)	0.6365 (2)	0.06941 (16)	0.0439 (4)
C14	1.5604 (2)	0.7614 (2)	0.01947 (16)	0.0492 (4)
H14A	1.6077	0.8305	−0.0448	0.059*
C15	1.3943 (2)	0.7820 (2)	0.06586 (16)	0.0487 (4)
H15A	1.3304	0.8663	0.0325	0.058*
C16	1.9073 (3)	0.7168 (3)	−0.0585 (2)	0.0675 (6)
H16A	2.0238	0.6843	−0.0727	0.101*
H16B	1.9003	0.8299	−0.0341	0.101*
H16C	1.8554	0.7100	−0.1304	0.101*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.06137 (14)	0.06633 (15)	0.05890 (14)	0.01421 (10)	0.01096 (9)	0.00724 (9)
O1	0.0370 (7)	0.1133 (13)	0.0702 (10)	−0.0055 (8)	−0.0113 (7)	−0.0132 (9)
O2	0.0440 (7)	0.0500 (7)	0.0654 (8)	0.0035 (5)	0.0050 (6)	0.0008 (6)
O3	0.0581 (8)	0.0542 (8)	0.0725 (9)	0.0160 (6)	0.0025 (7)	0.0021 (7)
O4	0.0462 (7)	0.0601 (8)	0.0664 (9)	0.0025 (6)	0.0045 (6)	0.0077 (7)
C1	0.0393 (8)	0.0515 (10)	0.0449 (9)	−0.0038 (7)	−0.0073 (7)	−0.0007 (7)
C2	0.0381 (8)	0.0516 (10)	0.0510 (10)	−0.0043 (7)	−0.0067 (7)	0.0056 (8)
C3	0.0470 (9)	0.0429 (9)	0.0442 (9)	0.0036 (7)	0.0014 (7)	0.0103 (7)
C4	0.0621 (11)	0.0497 (10)	0.0441 (10)	−0.0045 (8)	−0.0064 (8)	0.0000 (8)
C5	0.0470 (9)	0.0553 (11)	0.0489 (10)	−0.0104 (8)	−0.0114 (8)	0.0032 (8)
C6	0.0388 (8)	0.0468 (9)	0.0416 (9)	−0.0048 (7)	−0.0064 (7)	0.0069 (7)
C7	0.0370 (8)	0.0565 (11)	0.0505 (10)	−0.0035 (7)	−0.0067 (7)	0.0072 (8)
C8	0.0383 (9)	0.0569 (11)	0.0586 (11)	0.0000 (8)	−0.0005 (8)	−0.0037 (9)
C9	0.0481 (9)	0.0445 (9)	0.0462 (9)	0.0032 (7)	−0.0050 (7)	−0.0057 (7)
C10	0.0448 (9)	0.0388 (8)	0.0408 (9)	0.0015 (7)	−0.0050 (7)	−0.0058 (7)
C11	0.0463 (9)	0.0410 (9)	0.0448 (9)	−0.0028 (7)	−0.0049 (7)	0.0036 (7)
C12	0.0464 (9)	0.0416 (9)	0.0510 (10)	0.0008 (7)	−0.0091 (8)	0.0047 (7)
C13	0.0445 (9)	0.0430 (9)	0.0439 (9)	−0.0021 (7)	−0.0025 (7)	−0.0056 (7)
C14	0.0572 (11)	0.0451 (10)	0.0429 (9)	0.0013 (8)	0.0012 (8)	0.0030 (7)
C15	0.0563 (10)	0.0422 (9)	0.0465 (9)	0.0076 (8)	−0.0039 (8)	0.0018 (7)
C16	0.0556 (12)	0.0722 (14)	0.0686 (14)	−0.0042 (10)	0.0125 (10)	0.0063 (11)

Br1—C3	1.8925 (18)	C7—C8	1.511 (3)
O1—C7	1.207 (2)	C8—H8A	0.9700
O2—C9	1.346 (2)	C8—H8B	0.9700
O2—C8	1.429 (2)	C9—C10	1.475 (2)
O3—C9	1.203 (2)	C10—C15	1.384 (3)
O4—C13	1.356 (2)	C10—C11	1.394 (2)
O4—C16	1.428 (2)	C11—C12	1.371 (2)
C1—C2	1.389 (2)	C11—H11A	0.9300
C1—C6	1.389 (2)	C12—C13	1.389 (2)
C1—H1A	0.9300	C12—H12A	0.9300
C2—C3	1.376 (3)	C13—C14	1.387 (3)
C2—H2A	0.9300	C14—C15	1.378 (3)
C3—C4	1.385 (3)	C14—H14A	0.9300
C4—C5	1.374 (3)	C15—H15A	0.9300
C4—H4A	0.9300	C16—H16A	0.9600
C5—C6	1.392 (3)	C16—H16B	0.9600
C5—H5A	0.9300	C16—H16C	0.9600
C6—C7	1.488 (2)

C9—O2—C8	115.26 (14)	H8A—C8—H8B	108.0
C13—O4—C16	118.49 (15)	O3—C9—O2	123.12 (17)
C2—C1—C6	121.02 (17)	O3—C9—C10	124.67 (17)
C2—C1—H1A	119.5	O2—C9—C10	112.21 (14)
C6—C1—H1A	119.5	C15—C10—C11	118.55 (16)
C3—C2—C1	118.78 (16)	C15—C10—C9	118.67 (15)
C3—C2—H2A	120.6	C11—C10—C9	122.75 (16)
C1—C2—H2A	120.6	C12—C11—C10	120.37 (16)
C2—C3—C4	121.30 (17)	C12—C11—H11A	119.8
C2—C3—Br1	119.48 (14)	C10—C11—H11A	119.8
C4—C3—Br1	119.22 (14)	C11—C12—C13	120.61 (16)
C5—C4—C3	119.33 (18)	C11—C12—H12A	119.7
C5—C4—H4A	120.3	C13—C12—H12A	119.7
C3—C4—H4A	120.3	O4—C13—C14	124.61 (16)
C4—C5—C6	120.87 (17)	O4—C13—C12	115.91 (16)
C4—C5—H5A	119.6	C14—C13—C12	119.48 (16)
C6—C5—H5A	119.6	C15—C14—C13	119.44 (17)
C1—C6—C5	118.69 (17)	C15—C14—H14A	120.3
C1—C6—C7	122.38 (16)	C13—C14—H14A	120.3
C5—C6—C7	118.91 (16)	C14—C15—C10	121.49 (17)
O1—C7—C6	121.84 (18)	C14—C15—H15A	119.3
O1—C7—C8	119.99 (17)	C10—C15—H15A	119.3
C6—C7—C8	118.17 (15)	O4—C16—H16A	109.5
O2—C8—C7	111.04 (15)	O4—C16—H16B	109.5
O2—C8—H8A	109.4	H16A—C16—H16B	109.5
C7—C8—H8A	109.4	O4—C16—H16C	109.5
O2—C8—H8B	109.4	H16A—C16—H16C	109.5
C7—C8—H8B	109.4	H16B—C16—H16C	109.5

C6—C1—C2—C3	0.3 (3)	C8—O2—C9—C10	174.72 (15)
C1—C2—C3—C4	0.6 (3)	O3—C9—C10—C15	−15.5 (3)
C1—C2—C3—Br1	179.71 (13)	O2—C9—C10—C15	164.40 (16)
C2—C3—C4—C5	−0.9 (3)	O3—C9—C10—C11	162.56 (18)
Br1—C3—C4—C5	179.99 (14)	O2—C9—C10—C11	−17.5 (2)
C3—C4—C5—C6	0.3 (3)	C15—C10—C11—C12	1.5 (3)
C2—C1—C6—C5	−0.8 (3)	C9—C10—C11—C12	−176.60 (17)
C2—C1—C6—C7	−179.34 (17)	C10—C11—C12—C13	0.2 (3)
C4—C5—C6—C1	0.5 (3)	C16—O4—C13—C14	3.6 (3)
C4—C5—C6—C7	179.10 (17)	C16—O4—C13—C12	−176.97 (18)
C1—C6—C7—O1	−176.21 (19)	C11—C12—C13—O4	178.46 (17)
C5—C6—C7—O1	5.3 (3)	C11—C12—C13—C14	−2.1 (3)
C1—C6—C7—C8	3.8 (3)	O4—C13—C14—C15	−178.44 (17)
C5—C6—C7—C8	−174.72 (17)	C12—C13—C14—C15	2.2 (3)
C9—O2—C8—C7	−80.8 (2)	C13—C14—C15—C10	−0.4 (3)
O1—C7—C8—O2	−3.7 (3)	C11—C10—C15—C14	−1.4 (3)
C6—C7—C8—O2	176.31 (15)	C9—C10—C15—C14	176.76 (17)
C8—O2—C9—O3	−5.3 (3)

Cg1 is the centroid of the C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O1ⁱ	0.93	2.48	3.386 (2)	164
C11—H11A···Cg1ⁱⁱ	0.93	2.81	3.6395 (18)	149

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O1ⁱ	0.93	2.48	3.386 (2)	164
C11—H11A⋯Cg1ⁱⁱ	0.93	2.81	3.6395 (18)	149

Symmetry codes: (i) ; (ii) .

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1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. Chain mechanism in the photocleavage of phenacyl and pyridacyl esters in the presence of hydrogen donors.

Authors: Jaromír Literák; Anna Dostálová; Petr Klán
Journal: J Org Chem Date: 2006-01-20 Impact factor: 4.354

3. Structure validation in chemical crystallography.

Authors: Anthony L Spek
Journal: Acta Crystallogr D Biol Crystallogr Date: 2009-01-20

3 in total

7 in total

1. 2-(4-Bromo-phen-yl)-2-oxoethyl 4-chloro-benzoate.

Authors: Hoong-Kun Fun; Chin Sing Yeap; B Garudachari; Arun M Isloor; M N Satyanarayan
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2011-06-18

2. 2-(2,4-Dichloro-phen-yl)-2-oxoethyl 4-meth-oxy-benzoate.

Authors: Hoong-Kun Fun; Tze Shyang Chia; Seema Shenvi; Arun M Isloor; B Garudachari
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2011-11-19

3. 2-(4-Bromo-phen-yl)-2-oxoethyl 2-methyl-benzoate.

Authors: Hoong-Kun Fun; Chin Wei Ooi; B Garudachari; Arun M Isloor; M N Satyanarayan
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2011-10-29

4. Novel biphenyl ester derivatives as tyrosinase inhibitors: Synthesis, crystallographic, spectral analysis and molecular docking studies.

Authors: Huey Chong Kwong; C S Chidan Kumar; Siau Hui Mah; Tze Shyang Chia; Ching Kheng Quah; Zi Han Loh; Siddegowda Chandraju; Gin Keat Lim
Journal: PLoS One Date: 2017-02-27 Impact factor: 3.240