Literature DB >> 23476255

2-Oxo-2H-chromen-4-yl 4-meth-oxy-benzoate.

Akoun Abou1, Abdoulaye Djandé, Grégoire Danger, Adama Saba, Rita Kakou-Yao.   

Abstract

In the title mol-ecule, C17H12O5, the chromen-2-one ring and the 4-meth-oxy-benzoate side chain are inclined to one another at a dihedral angle of 69.82 (9)°. The crystal structure features parallel sheets of centrosymmetric R2(2)(6) dimers joined by a C(7) chain, resulting in centrosymetric tetra-mers of hydrogen-bonded mol-ecules with graph-set motif R4(4)(40). These centrosymetric tetra-mers are connected by a pair of hydrogen bonds described by an R2(2)(8) ring motif and a C(7) chain via C-H⋯O inter-actions. In the structure, there are also π-π stacking inter-actions between chromene benzene and the six-membered heterocyclic rings [centroid-centroid distance = 3.691 (2) Å] and weak C=O⋯π inter-actions [O⋯(ring centroid) distance = 3.357 (3) Å].

Entities:  

Year:  2012        PMID： 23476255      PMCID： PMC3589019          DOI： 10.1107/S1600536812047666

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


Related literature

For the biological activity of coumarin derivatives, see: Basanagouda et al. (2009 ▶); Vukovic et al. (2010 ▶); Emmanuel-Giota et al. (2001 ▶); Marchenko et al. (2006 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For π–π stacking inter­actions, see: Janiak (2000 ▶).

Experimental

Crystal data

C17H12O5 M = 296.27 Triclinic, a = 4.371 (1) Å b = 10.535 (4) Å c = 15.193 (2) Å α = 85.218 (3)° β = 83.688 (2)° γ = 81.893 (1)° V = 686.8 (3) Å3 Z = 2 Mo Kα radiation μ = 0.11 mm−1 T = 298 K 0.25 × 0.15 × 0.04 mm

Data collection

Nonius KappaCCD diffractometer 5683 measured reflections 2731 independent reflections 1540 reflections with I > 2σ(I) R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.066 wR(F 2) = 0.163 S = 1.11 2731 reflections 200 parameters H-atom parameters constrained Δρmax = 0.17 e Å−3 Δρmin = −0.23 e Å−3 Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97, publCIF (Westrip, 2010 ▶) and WinGX (Farrugia, 2012 ▶). Click here for additional data file. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812047666/zs2245sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812047666/zs2245Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536812047666/zs2245Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C17H12O5Z = 2
Mr = 296.27F(000) = 308
Triclinic, P1Dx = 1.433 Mg m−3
Hall symbol: -P 1Melting point = 421–422 K
a = 4.371 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.535 (4) ÅCell parameters from 5683 reflections
c = 15.193 (2) Åθ = 2.3–27.0°
α = 85.218 (3)°µ = 0.11 mm−1
β = 83.688 (2)°T = 298 K
γ = 81.893 (1)°Prism, colourless
V = 686.8 (3) Å30.25 × 0.15 × 0.04 mm
Nonius KappaCCD diffractometer1540 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.055
Graphite monochromatorθmax = 27.0°, θmin = 2.3°
φ and ω scansh = 0→5
5683 measured reflectionsk = −12→13
2731 independent reflectionsl = −18→19
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163H-atom parameters constrained
S = 1.11w = 1/[σ2(Fo2) + (0.0324P)2 + 0.5861P] where P = (Fo2 + 2Fc2)/3
2731 reflections(Δ/σ)max < 0.001
200 parametersΔρmax = 0.17 e Å−3
0 restraintsΔρmin = −0.23 e Å−3
48 constraints
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.
xyzUiso*/Ueq
O30.1598 (5)0.05340 (19)0.31179 (13)0.0542 (6)
O1−0.3230 (5)0.3325 (2)0.47003 (14)0.0528 (6)
O2−0.5808 (6)0.1879 (2)0.54685 (17)0.0722 (7)
C110.2683 (7)−0.0573 (3)0.1811 (2)0.0447 (7)
O4−0.1068 (6)0.1288 (2)0.19569 (15)0.0656 (7)
O50.7433 (6)−0.3598 (2)0.04518 (16)0.0702 (7)
C5−0.0670 (8)0.4966 (3)0.3926 (2)0.0525 (8)
H5−0.18390.55520.42970.063*
C9−0.0098 (7)0.1490 (3)0.3629 (2)0.0459 (8)
C10.0601 (7)0.2784 (3)0.3473 (2)0.0443 (7)
C6−0.1068 (7)0.3679 (3)0.4027 (2)0.0455 (8)
C140.5790 (7)−0.2567 (3)0.0861 (2)0.0512 (8)
C100.0876 (8)0.0505 (3)0.2267 (2)0.0500 (8)
C40.1473 (8)0.5360 (3)0.3273 (2)0.0586 (9)
H40.17580.62220.31990.070*
C7−0.3849 (8)0.2081 (3)0.4861 (2)0.0532 (8)
C120.4725 (7)−0.1501 (3)0.2215 (2)0.0510 (8)
H120.5054−0.14550.28050.061*
C150.3792 (8)−0.1649 (3)0.0454 (2)0.0612 (10)
H150.3468−0.1691−0.01380.073*
C8−0.2172 (8)0.1147 (3)0.4278 (2)0.0520 (8)
H8−0.25500.02960.43590.062*
C130.6278 (8)−0.2498 (3)0.1738 (2)0.0565 (9)
H130.7656−0.31250.20080.068*
C160.2264 (8)−0.0658 (3)0.0939 (2)0.0618 (10)
H160.0905−0.00270.06650.074*
C30.3223 (8)0.4490 (3)0.2719 (2)0.0585 (9)
H30.46920.47680.22830.070*
C20.2795 (7)0.3217 (3)0.2813 (2)0.0525 (8)
H20.39650.26390.24370.063*
C170.7156 (10)−0.3667 (4)−0.0473 (2)0.0784 (12)
H17A0.5023−0.3692−0.05600.118*
H17B0.8401−0.4429−0.06800.118*
H17C0.7859−0.2924−0.08000.118*
U11U22U33U12U13U23
O30.0695 (15)0.0459 (12)0.0453 (13)0.0091 (10)−0.0096 (11)−0.0155 (10)
O10.0634 (14)0.0459 (13)0.0478 (13)−0.0031 (10)0.0020 (11)−0.0138 (10)
O20.0892 (19)0.0661 (16)0.0575 (16)−0.0115 (13)0.0144 (14)−0.0096 (12)
C110.0515 (19)0.0393 (17)0.0429 (18)−0.0017 (13)−0.0024 (14)−0.0103 (14)
O40.0724 (16)0.0624 (15)0.0601 (15)0.0189 (12)−0.0207 (13)−0.0215 (12)
O50.0938 (19)0.0529 (14)0.0594 (16)0.0174 (13)−0.0090 (13)−0.0219 (12)
C50.060 (2)0.0451 (19)0.054 (2)0.0007 (15)−0.0131 (17)−0.0166 (15)
C90.057 (2)0.0391 (17)0.0418 (18)0.0060 (14)−0.0117 (16)−0.0130 (14)
C10.0482 (18)0.0443 (18)0.0404 (17)0.0026 (14)−0.0096 (14)−0.0106 (14)
C60.0508 (19)0.0458 (18)0.0407 (18)−0.0030 (14)−0.0080 (15)−0.0095 (14)
C140.060 (2)0.0394 (17)0.053 (2)0.0007 (15)−0.0023 (16)−0.0139 (15)
C100.055 (2)0.0488 (19)0.047 (2)−0.0023 (16)−0.0085 (16)−0.0116 (15)
C40.070 (2)0.047 (2)0.061 (2)−0.0107 (17)−0.0139 (19)−0.0028 (17)
C70.065 (2)0.049 (2)0.045 (2)−0.0026 (16)−0.0074 (17)−0.0086 (15)
C120.063 (2)0.0443 (18)0.0452 (19)−0.0020 (15)−0.0084 (16)−0.0076 (15)
C150.077 (2)0.059 (2)0.047 (2)0.0108 (18)−0.0159 (18)−0.0186 (17)
C80.066 (2)0.0430 (18)0.0464 (19)−0.0012 (15)−0.0070 (17)−0.0073 (15)
C130.071 (2)0.0420 (18)0.053 (2)0.0105 (16)−0.0108 (17)−0.0073 (16)
C160.078 (2)0.054 (2)0.051 (2)0.0165 (17)−0.0171 (18)−0.0157 (17)
C30.065 (2)0.062 (2)0.051 (2)−0.0137 (17)−0.0056 (17)−0.0051 (17)
C20.056 (2)0.057 (2)0.0447 (19)0.0012 (16)−0.0072 (16)−0.0129 (15)
C170.103 (3)0.071 (3)0.057 (2)0.015 (2)−0.006 (2)−0.029 (2)
O3—C101.368 (4)C14—C151.365 (4)
O3—C91.400 (3)C14—C131.381 (4)
O1—C71.373 (4)C4—C31.387 (5)
O1—C61.379 (4)C4—H40.9300
O2—C71.214 (4)C7—C81.445 (4)
C11—C161.369 (4)C12—C131.381 (4)
C11—C121.380 (4)C12—H120.9300
C11—C101.467 (4)C15—C161.379 (4)
O4—C101.204 (4)C15—H150.9300
O5—C141.370 (3)C8—H80.9300
O5—C171.433 (4)C13—H130.9300
C5—C41.368 (4)C16—H160.9300
C5—C61.385 (4)C3—C21.373 (4)
C5—H50.9300C3—H30.9300
C9—C81.327 (4)C2—H20.9300
C9—C11.434 (4)C17—H17A0.9600
C1—C61.391 (4)C17—H17B0.9600
C1—C21.403 (4)C17—H17C0.9600
C10—O3—C9117.2 (2)O1—C7—C8116.9 (3)
C7—O1—C6122.2 (2)C11—C12—C13119.6 (3)
C16—C11—C12119.0 (3)C11—C12—H12120.2
C16—C11—C10117.4 (3)C13—C12—H12120.2
C12—C11—C10123.6 (3)C14—C15—C16118.4 (3)
C14—O5—C17117.5 (3)C14—C15—H15120.8
C4—C5—C6118.9 (3)C16—C15—H15120.8
C4—C5—H5120.6C9—C8—C7120.8 (3)
C6—C5—H5120.6C9—C8—H8119.6
C8—C9—O3118.5 (3)C7—C8—H8119.6
C8—C9—C1122.3 (3)C12—C13—C14120.2 (3)
O3—C9—C1119.1 (3)C12—C13—H13119.9
C6—C1—C2117.9 (3)C14—C13—H13119.9
C6—C1—C9116.4 (3)C11—C16—C15122.1 (3)
C2—C1—C9125.7 (3)C11—C16—H16118.9
O1—C6—C5116.8 (3)C15—C16—H16118.9
O1—C6—C1121.3 (3)C2—C3—C4120.2 (3)
C5—C6—C1121.9 (3)C2—C3—H3119.9
C15—C14—O5123.9 (3)C4—C3—H3119.9
C15—C14—C13120.6 (3)C3—C2—C1120.4 (3)
O5—C14—C13115.5 (3)C3—C2—H2119.8
O4—C10—O3121.8 (3)C1—C2—H2119.8
O4—C10—C11125.8 (3)O5—C17—H17A109.5
O3—C10—C11112.4 (3)O5—C17—H17B109.5
C5—C4—C3120.8 (3)H17A—C17—H17B109.5
C5—C4—H4119.6O5—C17—H17C109.5
C3—C4—H4119.6H17A—C17—H17C109.5
O2—C7—O1116.6 (3)H17B—C17—H17C109.5
O2—C7—C8126.4 (3)
C10—O3—C9—C8107.7 (3)C6—C5—C4—C30.0 (5)
C10—O3—C9—C1−76.3 (4)C6—O1—C7—O2−179.7 (3)
C8—C9—C1—C6−1.4 (4)C6—O1—C7—C8−1.3 (4)
O3—C9—C1—C6−177.3 (3)C16—C11—C12—C13−0.6 (5)
C8—C9—C1—C2178.8 (3)C10—C11—C12—C13178.6 (3)
O3—C9—C1—C22.9 (5)O5—C14—C15—C16179.8 (3)
C7—O1—C6—C5179.5 (3)C13—C14—C15—C16−0.3 (5)
C7—O1—C6—C10.1 (4)O3—C9—C8—C7176.2 (3)
C4—C5—C6—O1179.4 (3)C1—C9—C8—C70.3 (5)
C4—C5—C6—C1−1.3 (5)O2—C7—C8—C9179.3 (3)
C2—C1—C6—O1−179.0 (3)O1—C7—C8—C91.1 (5)
C9—C1—C6—O11.2 (4)C11—C12—C13—C140.0 (5)
C2—C1—C6—C51.7 (4)C15—C14—C13—C120.5 (5)
C9—C1—C6—C5−178.1 (3)O5—C14—C13—C12−179.7 (3)
C17—O5—C14—C153.8 (5)C12—C11—C16—C150.7 (5)
C17—O5—C14—C13−176.1 (3)C10—C11—C16—C15−178.5 (3)
C9—O3—C10—O42.2 (5)C14—C15—C16—C11−0.3 (6)
C9—O3—C10—C11−177.0 (3)C5—C4—C3—C20.9 (5)
C16—C11—C10—O44.1 (5)C4—C3—C2—C1−0.5 (5)
C12—C11—C10—O4−175.1 (3)C6—C1—C2—C3−0.8 (5)
C16—C11—C10—O3−176.7 (3)C9—C1—C2—C3179.0 (3)
C12—C11—C10—O34.1 (4)
D—H···AD—HH···AD···AD—H···A
C8—H8···O2i0.932.483.407 (4)173
C2—H2···O4ii0.932.493.340 (4)151
C17—H17B···O5iii0.962.593.461 (4)151
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C8—H8⋯O2i 0.932.483.407 (4)173
C2—H2⋯O4ii 0.932.493.340 (4)151
C17—H17B⋯O5iii 0.962.593.461 (4)151

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

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