Literature DB >> 22347113

2-(4-Fluoro-phen-yl)-2-oxoethyl 2-methoxy-benzoate.

Arun M Isloor, B Garudachari, M N Satyanarayan, Thomas Gerber, Eric Hosten, Richard Betz.

Abstract

In the title compound, C(16)H(13)FO(4), the aromatic rings enclose an angle of 73.68 (6)°. In the crystal, C-H⋯O and C-H⋯F contacts connect the mol-ecules into a three-dimensional network. The shortest inter-centroid distance between two aromatic π-systems is 3.6679 (7) Å and is apparent between the fluorinated phenyl groups.

Entities: Chemical Disease Gene

Year: 2012 PMID： 22347113 PMCID： PMC3275257 DOI： 10.1107/S1600536812002577

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

Related literature

For general background to photosensitive protective groups and their synthetic potential, see: Sheehan & Umezaw (1973 ▶); Ruzicka et al. (2002 ▶); Litera et al. (2006 ▶); Rather & Reid (1919 ▶); Huang et al. (1996 ▶); Gandhi et al. (1995 ▶). For the graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶).

Experimental

Crystal data

C16H13FO4 M = 288.26 Monoclinic, a = 7.9370 (3) Å b = 26.4456 (9) Å c = 7.0635 (2) Å β = 113.404 (1)° V = 1360.64 (8) Å3 Z = 4 Mo Kα radiation μ = 0.11 mm−1 T = 200 K 0.43 × 0.32 × 0.27 mm

Data collection

Bruker APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.682, T max = 0.746 12541 measured reflections 3365 independent reflections 2927 reflections with I > 2σ(I) R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.037 wR(F 2) = 0.098 S = 1.04 3365 reflections 191 parameters H-atom parameters constrained Δρmax = 0.27 e Å−3 Δρmin = −0.16 e Å−3 Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶). Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812002577/gk2452sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812002577/gk2452Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812002577/gk2452Isup3.cdx Supplementary material file. DOI: 10.1107/S1600536812002577/gk2452Isup4.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₆H₁₃FO₄	F(000) = 600
M_r = 288.26	D_x = 1.407 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 359–360 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.9370 (3) Å	Cell parameters from 8158 reflections
b = 26.4456 (9) Å	θ = 2.3–28.3°
c = 7.0635 (2) Å	µ = 0.11 mm⁻¹
β = 113.404 (1)°	T = 200 K
V = 1360.64 (8) Å³	Platelet, colourless
Z = 4	0.43 × 0.32 × 0.27 mm

Bruker APEXII CCD diffractometer	3365 independent reflections
Radiation source: fine-focus sealed tube	2927 reflections with I > 2σ(I)
graphite	R_int = 0.027
φ and ω scans	θ_max = 28.3°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −10→10
T_min = 0.682, T_max = 0.746	k = −34→35
12541 measured reflections	l = −9→9

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.098	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0429P)² + 0.365P] where P = (F_o² + 2F_c²)/3
3365 reflections	(Δ/σ)_max < 0.001
191 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

	x	y	z	U_iso*/U_eq
F1	0.06897 (11)	−0.10183 (3)	1.15257 (13)	0.0497 (2)
O1	0.16097 (12)	0.14995 (4)	0.54890 (14)	0.0429 (2)
O2	0.44950 (11)	0.12318 (3)	0.72404 (13)	0.0378 (2)
O3	0.28771 (14)	0.03775 (4)	0.56649 (13)	0.0438 (2)
O4	0.09706 (11)	0.19590 (3)	0.19131 (13)	0.0399 (2)
C1	0.31601 (15)	0.14617 (4)	0.56176 (17)	0.0318 (2)
C2	0.30526 (15)	0.04439 (4)	0.74269 (16)	0.0307 (2)
C3	0.38626 (16)	0.09361 (4)	0.85111 (17)	0.0344 (2)
H3A	0.2919	0.1127	0.8803	0.041*
H3B	0.4897	0.0863	0.9840	0.041*
C4	−0.0169 (2)	0.21960 (6)	0.0007 (2)	0.0571 (4)
H4A	0.0247	0.2544	−0.0012	0.086*
H4B	−0.1445	0.2198	−0.0123	0.086*
H4C	−0.0087	0.2007	−0.1148	0.086*
C11	0.39019 (15)	0.16557 (4)	0.41277 (17)	0.0309 (2)
C12	0.27767 (15)	0.19075 (4)	0.23052 (18)	0.0317 (2)
C13	0.35424 (18)	0.20974 (5)	0.0989 (2)	0.0402 (3)
H13	0.2789	0.2272	−0.0230	0.048*
C14	0.5388 (2)	0.20346 (5)	0.1442 (2)	0.0473 (3)
H14	0.5895	0.2170	0.0537	0.057*
C15	0.65086 (18)	0.17783 (5)	0.3194 (2)	0.0466 (3)
H15	0.7773	0.1731	0.3484	0.056*
C16	0.57610 (17)	0.15923 (5)	0.4521 (2)	0.0391 (3)
H16	0.6530	0.1417	0.5729	0.047*
C21	0.24735 (14)	0.00579 (4)	0.85746 (16)	0.0282 (2)
C22	0.15576 (15)	−0.03738 (4)	0.75205 (17)	0.0325 (2)
H22	0.1341	−0.0415	0.6106	0.039*
C23	0.09629 (15)	−0.07416 (4)	0.85026 (18)	0.0354 (2)
H23	0.0339	−0.1035	0.7789	0.043*
C24	0.13080 (15)	−0.06672 (4)	1.05523 (18)	0.0345 (2)
C25	0.22246 (16)	−0.02547 (5)	1.16654 (17)	0.0348 (2)
H25	0.2459	−0.0222	1.3088	0.042*
C26	0.27973 (15)	0.01127 (4)	1.06578 (16)	0.0313 (2)
H26	0.3416	0.0405	1.1389	0.038*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0500 (5)	0.0474 (4)	0.0545 (5)	−0.0017 (3)	0.0238 (4)	0.0127 (3)
O1	0.0357 (5)	0.0503 (5)	0.0443 (5)	0.0094 (4)	0.0176 (4)	0.0130 (4)
O2	0.0321 (4)	0.0377 (4)	0.0370 (4)	−0.0012 (3)	0.0067 (3)	0.0070 (3)
O3	0.0579 (6)	0.0429 (5)	0.0307 (4)	−0.0036 (4)	0.0179 (4)	−0.0037 (3)
O4	0.0325 (4)	0.0410 (5)	0.0434 (5)	0.0045 (3)	0.0123 (4)	0.0132 (4)
C1	0.0322 (5)	0.0260 (5)	0.0333 (5)	0.0010 (4)	0.0090 (4)	−0.0001 (4)
C2	0.0283 (5)	0.0318 (5)	0.0276 (5)	0.0049 (4)	0.0065 (4)	0.0002 (4)
C3	0.0365 (6)	0.0319 (5)	0.0294 (5)	−0.0006 (4)	0.0074 (4)	0.0018 (4)
C4	0.0409 (7)	0.0620 (9)	0.0594 (8)	0.0071 (6)	0.0105 (6)	0.0307 (7)
C11	0.0312 (5)	0.0239 (5)	0.0368 (5)	−0.0018 (4)	0.0125 (4)	−0.0028 (4)
C12	0.0338 (5)	0.0227 (5)	0.0383 (6)	−0.0021 (4)	0.0140 (4)	−0.0021 (4)
C13	0.0480 (7)	0.0314 (6)	0.0443 (6)	−0.0039 (5)	0.0216 (5)	0.0018 (5)
C14	0.0528 (8)	0.0405 (7)	0.0609 (8)	−0.0084 (6)	0.0355 (7)	−0.0028 (6)
C15	0.0366 (6)	0.0422 (7)	0.0670 (9)	−0.0050 (5)	0.0270 (6)	−0.0084 (6)
C16	0.0329 (6)	0.0336 (6)	0.0484 (7)	0.0003 (4)	0.0134 (5)	−0.0029 (5)
C21	0.0251 (5)	0.0292 (5)	0.0271 (5)	0.0044 (4)	0.0070 (4)	−0.0017 (4)
C22	0.0306 (5)	0.0348 (5)	0.0281 (5)	0.0018 (4)	0.0074 (4)	−0.0046 (4)
C23	0.0302 (5)	0.0323 (5)	0.0389 (6)	0.0000 (4)	0.0085 (4)	−0.0040 (4)
C24	0.0293 (5)	0.0339 (6)	0.0399 (6)	0.0056 (4)	0.0134 (4)	0.0073 (4)
C25	0.0353 (6)	0.0403 (6)	0.0281 (5)	0.0069 (5)	0.0118 (4)	0.0004 (4)
C26	0.0306 (5)	0.0310 (5)	0.0286 (5)	0.0035 (4)	0.0079 (4)	−0.0045 (4)

F1—C24	1.3577 (13)	C13—C14	1.3799 (19)
O1—C1	1.2015 (14)	C13—H13	0.9500
O2—C1	1.3571 (13)	C14—C15	1.381 (2)
O2—C3	1.4236 (14)	C14—H14	0.9500
O3—C2	1.2090 (14)	C15—C16	1.3834 (19)
O4—C12	1.3545 (14)	C15—H15	0.9500
O4—C4	1.4339 (15)	C16—H16	0.9500
C1—C11	1.4865 (16)	C21—C26	1.3971 (14)
C2—C21	1.4853 (15)	C21—C22	1.3988 (15)
C2—C3	1.5177 (15)	C22—C23	1.3820 (17)
C3—H3A	0.9900	C22—H22	0.9500
C3—H3B	0.9900	C23—C24	1.3765 (17)
C4—H4A	0.9800	C23—H23	0.9500
C4—H4B	0.9800	C24—C25	1.3722 (17)
C4—H4C	0.9800	C25—C26	1.3835 (17)
C11—C16	1.3990 (16)	C25—H25	0.9500
C11—C12	1.4089 (15)	C26—H26	0.9500
C12—C13	1.3906 (16)

C1—O2—C3	115.22 (9)	C12—C13—H13	119.8
C12—O4—C4	117.22 (10)	C13—C14—C15	120.87 (12)
O1—C1—O2	122.26 (11)	C13—C14—H14	119.6
O1—C1—C11	126.84 (10)	C15—C14—H14	119.6
O2—C1—C11	110.90 (9)	C14—C15—C16	119.00 (12)
O3—C2—C21	121.88 (10)	C14—C15—H15	120.5
O3—C2—C3	119.77 (10)	C16—C15—H15	120.5
C21—C2—C3	118.35 (9)	C15—C16—C11	121.69 (12)
O2—C3—C2	109.74 (9)	C15—C16—H16	119.2
O2—C3—H3A	109.7	C11—C16—H16	119.2
C2—C3—H3A	109.7	C26—C21—C22	118.98 (10)
O2—C3—H3B	109.7	C26—C21—C2	122.43 (10)
C2—C3—H3B	109.7	C22—C21—C2	118.59 (9)
H3A—C3—H3B	108.2	C23—C22—C21	121.07 (10)
O4—C4—H4A	109.5	C23—C22—H22	119.5
O4—C4—H4B	109.5	C21—C22—H22	119.5
H4A—C4—H4B	109.5	C24—C23—C22	117.55 (11)
O4—C4—H4C	109.5	C24—C23—H23	121.2
H4A—C4—H4C	109.5	C22—C23—H23	121.2
H4B—C4—H4C	109.5	F1—C24—C25	118.00 (11)
C16—C11—C12	118.28 (11)	F1—C24—C23	118.29 (11)
C16—C11—C1	120.09 (10)	C25—C24—C23	123.70 (11)
C12—C11—C1	121.63 (10)	C24—C25—C26	118.12 (10)
O4—C12—C13	122.34 (11)	C24—C25—H25	120.9
O4—C12—C11	118.01 (10)	C26—C25—H25	120.9
C13—C12—C11	119.65 (11)	C25—C26—C21	120.56 (10)
C14—C13—C12	120.49 (12)	C25—C26—H26	119.7
C14—C13—H13	119.8	C21—C26—H26	119.7

C3—O2—C1—O1	14.38 (15)	C13—C14—C15—C16	−1.2 (2)
C3—O2—C1—C11	−166.53 (9)	C14—C15—C16—C11	0.23 (19)
C1—O2—C3—C2	75.18 (12)	C12—C11—C16—C15	1.31 (17)
O3—C2—C3—O2	−6.54 (15)	C1—C11—C16—C15	−178.44 (11)
C21—C2—C3—O2	174.23 (9)	O3—C2—C21—C26	174.92 (11)
O1—C1—C11—C16	178.44 (11)	C3—C2—C21—C26	−5.87 (15)
O2—C1—C11—C16	−0.61 (14)	O3—C2—C21—C22	−5.59 (16)
O1—C1—C11—C12	−1.31 (18)	C3—C2—C21—C22	173.62 (10)
O2—C1—C11—C12	179.65 (9)	C26—C21—C22—C23	0.49 (16)
C4—O4—C12—C13	3.34 (17)	C2—C21—C22—C23	−179.02 (10)
C4—O4—C12—C11	−177.26 (11)	C21—C22—C23—C24	−0.10 (16)
C16—C11—C12—O4	178.72 (10)	C22—C23—C24—F1	178.27 (10)
C1—C11—C12—O4	−1.53 (15)	C22—C23—C24—C25	−0.94 (17)
C16—C11—C12—C13	−1.87 (16)	F1—C24—C25—C26	−177.68 (10)
C1—C11—C12—C13	177.88 (10)	C23—C24—C25—C26	1.53 (17)
O4—C12—C13—C14	−179.70 (11)	C24—C25—C26—C21	−1.08 (16)
C11—C12—C13—C14	0.91 (17)	C22—C21—C26—C25	0.12 (16)
C12—C13—C14—C15	0.7 (2)	C2—C21—C26—C25	179.61 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···F1ⁱ	0.95	2.52	3.4335 (15)	162
C23—H23···O1ⁱⁱ	0.95	2.53	3.4004 (15)	152
C25—H25···O3ⁱⁱⁱ	0.95	2.34	3.1436 (14)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯F1ⁱ	0.95	2.52	3.4335 (15)	162
C23—H23⋯O1ⁱⁱ	0.95	2.53	3.4004 (15)	152
C25—H25⋯O3ⁱⁱⁱ	0.95	2.34	3.1436 (14)	142

Symmetry codes: (i) ; (ii) ; (iii) .

4 in total

1. A short history of SHELX.

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

2. Graph-set analysis of hydrogen-bond patterns in organic crystals.

Authors: M C Etter; J C MacDonald; J Bernstein
Journal: Acta Crystallogr B Date: 1990-04-01

3. 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

4. Structure validation in chemical crystallography.

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

4 in total

3 in total

1. 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

2. Crystal structure and Hirshfeld surface analysis of 2-(4-nitro-phen-yl)-2-oxoethyl picolinate.

Authors: T N Sanjeeva Murthy; C S Chidan Kumar; S Naveen; M K Veeraiah; Kakarla Raghava Reddy; Ismail Warad
Journal: Acta Crystallogr E Crystallogr Commun Date: 2019-10-29

3. Synthesis and Crystallographic Insight into the Structural Aspects of Some Novel Adamantane-Based Ester Derivatives.

Authors: C S Chidan Kumar; Huey Chong Kwong; Siau Hui Mah; Tze Shyang Chia; Wan-Sin Loh; Ching Kheng Quah; Gin Keat Lim; Siddegowda Chandraju; Hoong-Kun Fun
Journal: Molecules Date: 2015-10-16 Impact factor: 4.411

3 in total