Literature DB >> 25878887

Crystal structure of 3-[2-(4-methyl-phen-yl)ethyn-yl]-2H-chromen-2-one.

Ignez Caracelli¹, Stella H Maganhi¹, Hélio A Stefani², Karina Gueogjian², Edward R T Tiekink³.

Abstract

The coumarin ring system in the title asymmetric alkyne, C18H12O2, is approximately planar (r.m.s. deviation of the 11 non-H atoms = 0.048 Å), and is inclined with respect to the methyl-benzene ring, forming a dihedral angle of 33.68 (4)°. In the crystal, supra-molecular zigzag chains along the c-axis direction are formed via weak C-H⋯O hydrogen bonds, and these are connected into double layers via weak C-H⋯π inter-actions; these stack along the a axis.

Entities: Chemical Disease Species

Keywords: C—H⋯π interactions; asymmetric alkyne; coumarins; crystal structure; hydrogen bonding

Year: 2015 PMID： 25878887 PMCID： PMC4384545 DOI： 10.1107/S2056989014027790

Source DB: PubMed Journal: Acta Crystallogr E Crystallogr Commun

Related literature

For the biological activity of coumarins, see: Wu et al. (2009 ▸). For background to previous work on coumarins, see: Stefani et al. (2012 ▸). For a related structure, see: Elangovan et al. (2004 ▸). For synthetic details, see: Gueogjian (2011 ▸).

Experimental

Crystal data

C18H12O2 M = 260.28 Monoclinic, a = 8.4695 (2) Å b = 10.6759 (2) Å c = 14.5208 (2) Å β = 98.093 (2)° V = 1299.89 (4) Å3 Z = 4 Cu Kα radiation μ = 0.69 mm−1 T = 100 K 0.30 × 0.25 × 0.20 mm

Data collection

Agilent CCD diffratcometer diffractometer Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▸) T min = 0.834, T max = 1.000 5023 measured reflections 2664 independent reflections 2416 reflections with I > 2σ(I) R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.038 wR(F 2) = 0.105 S = 1.04 2664 reflections 182 parameters H-atom parameters constrained Δρmax = 0.25 e Å−3 Δρmin = −0.21 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▸); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2014 (Burla et al., 2015 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸) and DIAMOND (Brandenburg, 2006 ▸); software used to prepare material for publication: MarvinSketch (ChemAxon, 2010 ▸) and publCIF (Westrip, 2010 ▸). Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989014027790/hg5424sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989014027790/hg5424Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S2056989014027790/hg5424Isup3.cml Click here for additional data file. . DOI: 10.1107/S2056989014027790/hg5424fig1.tif The molecular structure of the title compound showing the atom-labelling scheme and displacement ellipsoids at the 70% probability level. Click here for additional data file. c . DOI: 10.1107/S2056989014027790/hg5424fig2.tif A view of the zigzag supramolecular sustained by weak C—H⋯O hydrogen bonds (orange dashed lines) and aligned along the c axis in the crystal packing. Click here for additional data file. c . DOI: 10.1107/S2056989014027790/hg5424fig3.tif A view in projection down the c axis of the unit-cell contents. The weak C—H⋯O and C—H⋯π interactions are shown as orange and purple dashed lines, respectively. CCDC reference: 1040558 Additional supporting information: crystallographic information; 3D view; checkCIF report

C₁₈H₁₂O₂	F(000) = 544
M_r = 260.28	D_x = 1.330 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
a = 8.4695 (2) Å	Cell parameters from 3107 reflections
b = 10.6759 (2) Å	θ = 3.1–76.1°
c = 14.5208 (2) Å	µ = 0.69 mm⁻¹
β = 98.093 (2)°	T = 100 K
V = 1299.89 (4) Å³	Prism, dark orange
Z = 4	0.30 × 0.25 × 0.20 mm

Agilent CCD diffratcometer diffractometer	2416 reflections with I > 2σ(I)
Radiation source: SuperNova (Cu) X-ray Source	R_int = 0.015
ω scans	θ_max = 76.3°, θ_min = 5.2°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	h = −9→10
T_min = 0.834, T_max = 1.000	k = −6→13
5023 measured reflections	l = −17→18
2664 independent reflections

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.038	H-atom parameters constrained
wR(F²) = 0.105	w = 1/[σ²(F_o²) + (0.0605P)² + 0.3358P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2664 reflections	Δρ_max = 0.25 e Å⁻³
182 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints

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.

	x	y	z	U_iso*/U_eq
O1	0.13803 (10)	0.67272 (7)	0.66818 (5)	0.0210 (2)
O2	0.15964 (12)	0.72775 (8)	0.52430 (6)	0.0313 (2)
C1	0.16397 (14)	0.64322 (11)	0.57962 (7)	0.0211 (2)
C2	0.19557 (13)	0.51127 (11)	0.56003 (7)	0.0199 (2)
C3	0.18389 (13)	0.42253 (10)	0.62585 (7)	0.0199 (2)
H3	0.1980	0.3368	0.6115	0.024*
C4	0.15055 (13)	0.45668 (10)	0.71666 (7)	0.0184 (2)
C5	0.14038 (13)	0.36959 (11)	0.78810 (8)	0.0206 (2)
H5	0.1504	0.2826	0.7763	0.025*
C6	0.11585 (13)	0.40976 (11)	0.87544 (8)	0.0217 (2)
H6	0.1078	0.3504	0.9233	0.026*
C7	0.10299 (13)	0.53744 (11)	0.89331 (7)	0.0213 (2)
H7	0.0880	0.5645	0.9538	0.026*
C8	0.11176 (13)	0.62546 (11)	0.82380 (7)	0.0204 (2)
H8	0.1033	0.7124	0.8360	0.025*
C9	0.13313 (13)	0.58337 (10)	0.73620 (7)	0.0181 (2)
C10	0.24056 (14)	0.48424 (11)	0.47093 (8)	0.0219 (2)
C11	0.28627 (14)	0.46381 (11)	0.39787 (8)	0.0213 (2)
C12	0.34093 (13)	0.43519 (11)	0.31108 (7)	0.0191 (2)
C13	0.28464 (13)	0.50208 (11)	0.23036 (8)	0.0214 (2)
H13	0.2132	0.5701	0.2333	0.026*
C14	0.33248 (14)	0.46968 (12)	0.14599 (8)	0.0227 (3)
H14	0.2941	0.5166	0.0919	0.027*
C15	0.43582 (13)	0.36949 (11)	0.13914 (8)	0.0215 (2)
C16	0.49343 (14)	0.30434 (11)	0.22028 (8)	0.0229 (2)
H16	0.5653	0.2366	0.2172	0.027*
C17	0.44814 (14)	0.33623 (11)	0.30511 (8)	0.0218 (2)
H17	0.4897	0.2910	0.3595	0.026*
C18	0.48231 (15)	0.32959 (13)	0.04694 (8)	0.0286 (3)
H18A	0.4267	0.3821	−0.0027	0.043*
H18B	0.4526	0.2417	0.0351	0.043*
H18C	0.5978	0.3390	0.0486	0.043*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0288 (4)	0.0177 (4)	0.0170 (4)	0.0023 (3)	0.0054 (3)	0.0017 (3)
O2	0.0459 (6)	0.0265 (5)	0.0239 (4)	0.0070 (4)	0.0132 (4)	0.0074 (3)
C1	0.0237 (6)	0.0236 (6)	0.0164 (5)	0.0020 (4)	0.0046 (4)	0.0019 (4)
C2	0.0189 (5)	0.0235 (6)	0.0170 (5)	0.0023 (4)	0.0016 (4)	−0.0011 (4)
C3	0.0198 (5)	0.0201 (5)	0.0195 (5)	0.0020 (4)	0.0018 (4)	−0.0012 (4)
C4	0.0168 (5)	0.0201 (5)	0.0179 (5)	0.0009 (4)	0.0009 (4)	0.0001 (4)
C5	0.0202 (5)	0.0193 (5)	0.0217 (5)	0.0006 (4)	0.0008 (4)	0.0021 (4)
C6	0.0211 (5)	0.0252 (6)	0.0182 (5)	−0.0015 (4)	0.0003 (4)	0.0051 (4)
C7	0.0205 (5)	0.0282 (6)	0.0148 (5)	−0.0019 (4)	0.0007 (4)	−0.0009 (4)
C8	0.0216 (5)	0.0207 (5)	0.0187 (5)	−0.0006 (4)	0.0018 (4)	−0.0017 (4)
C9	0.0183 (5)	0.0194 (5)	0.0163 (5)	0.0001 (4)	0.0013 (4)	0.0023 (4)
C10	0.0223 (5)	0.0241 (5)	0.0189 (5)	0.0014 (4)	0.0018 (4)	−0.0002 (4)
C11	0.0213 (5)	0.0226 (5)	0.0197 (5)	−0.0006 (4)	0.0013 (4)	−0.0009 (4)
C12	0.0191 (5)	0.0214 (5)	0.0169 (5)	−0.0036 (4)	0.0027 (4)	−0.0027 (4)
C13	0.0196 (5)	0.0231 (6)	0.0209 (5)	0.0012 (4)	0.0013 (4)	−0.0014 (4)
C14	0.0218 (5)	0.0292 (6)	0.0164 (5)	−0.0008 (5)	−0.0006 (4)	0.0012 (4)
C15	0.0191 (5)	0.0278 (6)	0.0178 (5)	−0.0054 (4)	0.0030 (4)	−0.0048 (4)
C16	0.0211 (5)	0.0231 (6)	0.0250 (6)	0.0013 (4)	0.0053 (4)	−0.0022 (4)
C17	0.0229 (5)	0.0238 (6)	0.0184 (5)	−0.0002 (4)	0.0021 (4)	0.0023 (4)
C18	0.0274 (6)	0.0394 (7)	0.0200 (6)	−0.0036 (5)	0.0062 (5)	−0.0074 (5)

O1—C1	1.3713 (13)	C8—H8	0.9500
O1—C9	1.3780 (13)	C10—C11	1.1995 (16)
O2—C1	1.2053 (14)	C11—C12	1.4353 (15)
C1—C2	1.4691 (16)	C12—C13	1.3978 (16)
C2—C3	1.3592 (15)	C12—C17	1.4036 (16)
C2—C10	1.4287 (15)	C13—C14	1.3873 (15)
C3—C4	1.4339 (14)	C13—H13	0.9500
C3—H3	0.9500	C14—C15	1.3945 (17)
C4—C9	1.3941 (15)	C14—H14	0.9500
C4—C5	1.4048 (15)	C15—C16	1.3958 (16)
C5—C6	1.3820 (15)	C15—C18	1.5090 (14)
C5—H5	0.9500	C16—C17	1.3833 (15)
C6—C7	1.3946 (17)	C16—H16	0.9500
C6—H6	0.9500	C17—H17	0.9500
C7—C8	1.3887 (16)	C18—H18A	0.9800
C7—H7	0.9500	C18—H18B	0.9800
C8—C9	1.3847 (15)	C18—H18C	0.9800

C1—O1—C9	122.56 (9)	C8—C9—C4	122.22 (10)
O2—C1—O1	117.33 (10)	C11—C10—C2	176.53 (12)
O2—C1—C2	125.32 (10)	C10—C11—C12	178.19 (12)
O1—C1—C2	117.35 (9)	C13—C12—C17	118.68 (10)
C3—C2—C10	123.44 (11)	C13—C12—C11	120.89 (10)
C3—C2—C1	119.92 (10)	C17—C12—C11	120.39 (10)
C10—C2—C1	116.62 (10)	C14—C13—C12	120.37 (11)
C2—C3—C4	120.84 (10)	C14—C13—H13	119.8
C2—C3—H3	119.6	C12—C13—H13	119.8
C4—C3—H3	119.6	C13—C14—C15	121.24 (10)
C9—C4—C5	118.20 (10)	C13—C14—H14	119.4
C9—C4—C3	118.30 (10)	C15—C14—H14	119.4
C5—C4—C3	123.46 (10)	C14—C15—C16	118.05 (10)
C6—C5—C4	120.34 (11)	C14—C15—C18	121.64 (11)
C6—C5—H5	119.8	C16—C15—C18	120.29 (11)
C4—C5—H5	119.8	C17—C16—C15	121.42 (11)
C5—C6—C7	119.99 (10)	C17—C16—H16	119.3
C5—C6—H6	120.0	C15—C16—H16	119.3
C7—C6—H6	120.0	C16—C17—C12	120.21 (10)
C8—C7—C6	120.84 (10)	C16—C17—H17	119.9
C8—C7—H7	119.6	C12—C17—H17	119.9
C6—C7—H7	119.6	C15—C18—H18A	109.5
C9—C8—C7	118.38 (10)	C15—C18—H18B	109.5
C9—C8—H8	120.8	H18A—C18—H18B	109.5
C7—C8—H8	120.8	C15—C18—H18C	109.5
O1—C9—C8	117.06 (10)	H18A—C18—H18C	109.5
O1—C9—C4	120.72 (9)	H18B—C18—H18C	109.5

C9—O1—C1—O2	177.09 (10)	C7—C8—C9—O1	178.68 (9)
C9—O1—C1—C2	−3.21 (15)	C7—C8—C9—C4	−1.88 (17)
O2—C1—C2—C3	−174.34 (12)	C5—C4—C9—O1	−178.37 (9)
O1—C1—C2—C3	5.98 (16)	C3—C4—C9—O1	3.95 (16)
O2—C1—C2—C10	6.73 (18)	C5—C4—C9—C8	2.21 (16)
O1—C1—C2—C10	−172.95 (10)	C3—C4—C9—C8	−175.47 (10)
C10—C2—C3—C4	175.00 (10)	C17—C12—C13—C14	0.91 (16)
C1—C2—C3—C4	−3.86 (17)	C11—C12—C13—C14	−176.91 (10)
C2—C3—C4—C9	−1.08 (16)	C12—C13—C14—C15	0.70 (17)
C2—C3—C4—C5	−178.62 (10)	C13—C14—C15—C16	−1.63 (17)
C9—C4—C5—C6	−0.84 (16)	C13—C14—C15—C18	177.00 (11)
C3—C4—C5—C6	176.70 (10)	C14—C15—C16—C17	0.99 (17)
C4—C5—C6—C7	−0.77 (17)	C18—C15—C16—C17	−177.67 (10)
C5—C6—C7—C8	1.12 (17)	C15—C16—C17—C12	0.60 (18)
C6—C7—C8—C9	0.18 (17)	C13—C12—C17—C16	−1.54 (17)
C1—O1—C9—C8	177.74 (10)	C11—C12—C17—C16	176.28 (10)
C1—O1—C9—C4	−1.71 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O2ⁱ	0.95	2.48	3.1425 (14)	127
C13—H13···Cg1ⁱⁱ	0.95	2.94	3.4416 (12)	115
C5—H5···Cg2ⁱⁱⁱ	0.95	3.00	3.7780 (13)	140

Table 1

Hydrogen-bond geometry (, )

Cg1 and Cg2 are the centroids of the C4C9 and C12C17 rings, respectively.

DHA	DH	HA	D A	DHA
C7H7O2ⁱ	0.95	2.48	3.1425(14)	127
C13H13Cg1ⁱⁱ	0.95	2.94	3.4416(12)	115
C5H5Cg2ⁱⁱⁱ	0.95	3.00	3.7780(13)	140

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

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Authors: George M Sheldrick
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