Literature DB >> 21203095

2-Methyl-3-(3-methyl-phen-yl)acrylic acid.

Niaz Muhammad, Saqib Ali, M Nawaz Tahir.

Abstract

The crystal structure of the title compound, C(11)H(12)O(2), consists of dimers which are formed due to inter-molecular O-H⋯O hydrogen bonding. The dimers are linked to each other by C-H⋯O hydrogen bonds, where C-H belongs to the benzene ring and the O atom is of a carbonyl group of an adjoining mol-ecule. There exist two inter-molecular C-H⋯O hydrogen bonds which form five-membered rings. There exist two π-π inter-actions between the benzene rings. The perpendicular distance in these inter-actions are 3.006 and 3.396 Å. There also exist C-H⋯π and C-O⋯π inter-actions.

Entities: Chemical Disease Gene

Year: 2008 PMID： 21203095 PMCID： PMC2962008 DOI： 10.1107/S1600536808019545

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

Related literature

For related literature, see: Bernstein et al. (1995 ▶); Liu et al. (1999 ▶); Muhammad et al. (2007 ▶); Natella et al. (1999 ▶); Niaz et al. (2008 ▶); Parez-Alvarez et al. (2001 ▶); Wiesner et al. (2001 ▶).

Experimental

Crystal data

C11H12O2 M = 176.21 Monoclinic, a = 7.4430 (9) Å b = 13.4094 (16) Å c = 10.2746 (12) Å β = 110.745 (4)° V = 959.0 (2) Å3 Z = 4 Mo Kα radiation μ = 0.08 mm−1 T = 296 (2) K 0.26 × 0.18 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.980, T max = 0.986 11342 measured reflections 2820 independent reflections 1075 reflections with I > 2σ(I) R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.056 wR(F 2) = 0.185 S = 1.02 2820 reflections 120 parameters H-atom parameters constrained Δρmax = 0.23 e Å−3 Δρmin = −0.20 e Å−3 Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007 ▶); 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, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999 ▶) and PLATON. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808019545/at2580sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019545/at2580Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₁H₁₂O₂	F₀₀₀ = 376
M_r = 176.21	D_x = 1.220 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2820 reflections
a = 7.4430 (9) Å	θ = 2.6–30.2º
b = 13.4094 (16) Å	µ = 0.08 mm⁻¹
c = 10.2746 (12) Å	T = 296 (2) K
β = 110.745 (4)º	Prismatic, colourless
V = 959.0 (2) Å³	0.26 × 0.18 × 0.15 mm
Z = 4

Bruker KAPPA APEXII CCD diffractometer	2820 independent reflections
Radiation source: fine-focus sealed tube	1075 reflections with I > 2σ(I)
Monochromator: graphite	R_int = 0.047
Detector resolution: 7.2 pixels mm^-1	θ_max = 30.2º
T = 296(2) K	θ_min = 2.6º
ω scans	h = −10→8
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −18→13
T_min = 0.980, T_max = 0.986	l = −10→14
11342 measured reflections

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.056	w = 1/[σ²(F_o²) + (0.0657P)² + 0.191P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.185	(Δ/σ)_max < 0.001
S = 1.02	Δρ_max = 0.24 e Å⁻³
2820 reflections	Δρ_min = −0.20 e Å⁻³
120 parameters	Extinction correction: empirical, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.006 (2)
Secondary atom site location: difference Fourier map

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
O1	0.1630 (3)	−0.00578 (12)	0.4174 (2)	0.0795 (8)
O2	0.0675 (2)	0.12222 (11)	0.51106 (18)	0.0699 (7)
C1	0.1639 (3)	0.08682 (17)	0.4441 (2)	0.0515 (8)
C2	0.2797 (3)	0.15393 (16)	0.3911 (2)	0.0484 (7)
C3	0.4010 (3)	0.11136 (17)	0.3377 (2)	0.0533 (8)
C4	0.5340 (3)	0.15354 (16)	0.2764 (2)	0.0497 (8)
C5	0.6214 (3)	0.08770 (17)	0.2126 (2)	0.0534 (8)
C6	0.7448 (3)	0.11877 (18)	0.1461 (2)	0.0553 (8)
C7	0.7829 (4)	0.21882 (19)	0.1470 (3)	0.0637 (9)
C8	0.7031 (4)	0.2856 (2)	0.2118 (3)	0.0699 (10)
C9	0.5794 (4)	0.25412 (17)	0.2757 (3)	0.0646 (9)
C10	0.2492 (3)	0.26372 (17)	0.4024 (3)	0.0658 (10)
C11	0.8342 (4)	0.0464 (2)	0.0760 (3)	0.0788 (11)
H1	0.10360	−0.03595	0.45872	0.0954*
H3	0.40046	0.04203	0.33992	0.0639*
H5	0.59610	0.01991	0.21458	0.0640*
H7	0.86445	0.24181	0.10285	0.0764*
H8	0.73305	0.35299	0.21244	0.0838*
H9	0.52556	0.30031	0.31872	0.0774*
H10A	0.15463	0.27413	0.44482	0.0988*
H10B	0.20537	0.29296	0.31123	0.0988*
H10C	0.36802	0.29433	0.45849	0.0988*
H11A	0.79146	−0.01992	0.08522	0.1182*
H11B	0.97157	0.04960	0.11877	0.1182*
H11C	0.79701	0.06301	−0.02083	0.1182*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.1052 (15)	0.0487 (10)	0.1240 (17)	−0.0062 (9)	0.0893 (13)	−0.0004 (10)
O2	0.0786 (12)	0.0602 (11)	0.0958 (13)	−0.0042 (8)	0.0617 (11)	−0.0100 (9)
C1	0.0537 (13)	0.0479 (13)	0.0629 (15)	0.0003 (10)	0.0330 (12)	−0.0028 (11)
C2	0.0460 (12)	0.0467 (12)	0.0570 (14)	−0.0032 (10)	0.0239 (11)	0.0020 (11)
C3	0.0583 (14)	0.0481 (12)	0.0634 (15)	−0.0046 (11)	0.0339 (12)	0.0003 (12)
C4	0.0510 (13)	0.0508 (12)	0.0549 (14)	−0.0052 (10)	0.0282 (12)	0.0009 (11)
C5	0.0525 (14)	0.0513 (13)	0.0611 (15)	−0.0035 (10)	0.0261 (12)	0.0021 (11)
C6	0.0490 (13)	0.0649 (16)	0.0589 (15)	−0.0034 (11)	0.0278 (12)	0.0047 (12)
C7	0.0631 (15)	0.0742 (17)	0.0646 (16)	−0.0139 (13)	0.0358 (14)	0.0053 (13)
C8	0.0812 (19)	0.0581 (15)	0.0849 (19)	−0.0194 (13)	0.0475 (17)	−0.0021 (13)
C9	0.0767 (17)	0.0525 (14)	0.0804 (18)	−0.0098 (12)	0.0475 (15)	−0.0045 (13)
C10	0.0574 (15)	0.0538 (15)	0.097 (2)	−0.0010 (11)	0.0408 (15)	−0.0017 (14)
C11	0.0757 (18)	0.088 (2)	0.091 (2)	0.0014 (15)	0.0521 (17)	−0.0051 (16)

O1—C1	1.271 (3)	C8—C9	1.373 (4)
O2—C1	1.250 (3)	C3—H3	0.9300
O1—H1	0.8200	C5—H5	0.9300
C1—C2	1.477 (3)	C7—H7	0.9300
C2—C10	1.500 (3)	C8—H8	0.9300
C2—C3	1.339 (3)	C9—H9	0.9300
C3—C4	1.462 (3)	C10—H10A	0.9600
C4—C9	1.391 (3)	C10—H10B	0.9600
C4—C5	1.391 (3)	C10—H10C	0.9600
C5—C6	1.389 (3)	C11—H11A	0.9600
C6—C7	1.371 (4)	C11—H11B	0.9600
C6—C11	1.498 (4)	C11—H11C	0.9600
C7—C8	1.370 (4)

C1—O1—H1	109.00	C4—C5—H5	119.00
O1—C1—O2	122.0 (2)	C6—C5—H5	119.00
O1—C1—C2	118.3 (2)	C6—C7—H7	119.00
O2—C1—C2	119.7 (2)	C8—C7—H7	119.00
C1—C2—C10	116.4 (2)	C7—C8—H8	120.00
C3—C2—C10	126.3 (2)	C9—C8—H8	120.00
C1—C2—C3	117.2 (2)	C4—C9—H9	120.00
C2—C3—C4	132.0 (2)	C8—C9—H9	120.00
C3—C4—C9	125.5 (2)	C2—C10—H10A	109.00
C5—C4—C9	117.3 (2)	C2—C10—H10B	109.00
C3—C4—C5	117.3 (2)	C2—C10—H10C	109.00
C4—C5—C6	122.9 (2)	H10A—C10—H10B	109.00
C5—C6—C11	121.8 (2)	H10A—C10—H10C	109.00
C7—C6—C11	120.8 (2)	H10B—C10—H10C	109.00
C5—C6—C7	117.5 (2)	C6—C11—H11A	109.00
C6—C7—C8	121.2 (3)	C6—C11—H11B	109.00
C7—C8—C9	120.7 (2)	C6—C11—H11C	110.00
C4—C9—C8	120.4 (2)	H11A—C11—H11B	109.00
C2—C3—H3	114.00	H11A—C11—H11C	109.00
C4—C3—H3	114.00	H11B—C11—H11C	109.00

O1—C1—C2—C3	−10.6 (3)	C9—C4—C5—C6	−2.0 (3)
O1—C1—C2—C10	169.3 (2)	C3—C4—C9—C8	−178.4 (2)
O2—C1—C2—C3	170.7 (2)	C5—C4—C9—C8	1.2 (4)
O2—C1—C2—C10	−9.4 (3)	C4—C5—C6—C7	1.3 (3)
C1—C2—C3—C4	179.6 (2)	C4—C5—C6—C11	−178.9 (2)
C10—C2—C3—C4	−0.3 (4)	C5—C6—C7—C8	0.4 (4)
C2—C3—C4—C5	−171.3 (2)	C11—C6—C7—C8	−179.5 (3)
C2—C3—C4—C9	8.3 (4)	C6—C7—C8—C9	−1.2 (4)
C3—C4—C5—C6	177.54 (19)	C7—C8—C9—C4	0.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2ⁱ	0.82	1.83	2.611 (3)	160
C3—H3···O1	0.93	2.27	2.703 (3)	108
C8—H8···O1ⁱⁱ	0.93	2.59	3.394 (3)	145
C10—H10A···O2	0.96	2.31	2.783 (3)	109
C10—H10C···Cgⁱⁱⁱ	0.9600	2.75	3.610 (3)	149.00
C1—O2···Cg^iv	1.250 (3)	3.574 (2)	3.895 (3)	95.38 (13)

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C4–C9 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.82	1.83	2.611 (3)	160
C3—H3⋯O1	0.93	2.27	2.703 (3)	108
C8—H8⋯O1ⁱⁱ	0.93	2.59	3.394 (3)	145
C10—H10A⋯O2	0.96	2.31	2.783 (3)	109
C10—H10C⋯Cgⁱⁱⁱ	0.96	2.75	3.610 (3)	149
C1—O2⋯Cg^iv	1.25 (1)	3.57 (1)	3.895 (3)	95 (1)

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

6 in total

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Authors: I M Liu; T C Chi; F L Hsu; C F Chen; J T Cheng
Journal: Planta Med Date: 1999-12 Impact factor: 3.352

2. A short history of SHELX.

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

3. Structure-hepatoprotective activity relationship of 3,4-dihydroxycinnamic acid (caffeic acid) derivatives.

Authors: V Pérez-Alvarez; R A Bobadilla; P Muriel
Journal: J Appl Toxicol Date: 2001 Nov-Dec Impact factor: 3.446

4. Benzoic and cinnamic acid derivatives as antioxidants: structure-activity relation.

Authors: F Natella; M Nardini; M Di Felice; C Scaccini
Journal: J Agric Food Chem Date: 1999-04 Impact factor: 5.279

5. Structure-activity relationships of novel anti-malarial agents. Part 2: cinnamic acid derivatives.

Authors: J Wiesner; A Mitsch; P Wissner; H Jomaa; M Schlitzer
Journal: Bioorg Med Chem Lett Date: 2001-02-12 Impact factor: 2.823

6. (E)-2-(2-Fluoro-benzyl-idene)butanoic acid.

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