Literature DB >> 26090173

Crystal structure of 4-meth-oxy-phenyl 2-oxo-2H-chromene-3-carboxyl-ate.

H C Devarajegowda¹, P A Suchetan², S Sreenivasa², H T Srinivasa³, B S Palakshamurthy¹.

Abstract

In the title compound, C17H12O5, the dihedral angle between the planes of the coumarin ring system (r.m.s. deviation = 0.015 Å) and the benzene ring is 48.04 (10)°. The central CO2 group subtends a dihedral angle of 27.15 (11)° with the coumarin ring system and 74.86 (13)° with the benzene ring. In the crystal, mol-ecules are linked by C-H⋯O inter-actions, which generate a three-dimensional network. Very weak C-H⋯π inter-actions are also observed.

Entities: CellLine Chemical Disease Gene Species

Keywords: 2-oxo-2H-chromene; C—H⋯O interactions; C—H⋯π interactions; crystal structure

Year: 2015 PMID： 26090173 PMCID： PMC4459373 DOI： 10.1107/S2056989015006970

Source DB: PubMed Journal: Acta Crystallogr E Crystallogr Commun

Related literature

For details of the biological activies of 2-oxo-2H-chromene derivatives, see: Kawase et al. (2001 ▸); Traven (2004 ▸); Lacy & O’Kennedy (2004 ▸); Chimenti et al. (2009 ▸). For related structures, see: Sreenivasa et al. (2013 ▸); Devarajegowda et al., (2013 ▸).

Experimental

Crystal data

C17H12O5 M = 296.27 Orthorhombic, a = 6.2648 (18) Å b = 10.435 (3) Å c = 20.621 (7) Å V = 1348.0 (7) Å3 Z = 4 Mo Kα radiation μ = 0.11 mm−1 T = 296 K 0.22 × 0.20 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2013 ▸) T min = 0.977, T max = 0.981 10472 measured reflections 2385 independent reflections 2150 reflections with I > 2σ(I) R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.035 wR(F 2) = 0.085 S = 1.09 1411 reflections 201 parameters H-atom parameters constrained Δρmax = 0.16 e Å−3 Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2013 ▸); cell refinement: SAINT (Bruker, 2013 ▸); data reduction: SAINT (Bruker, 2013 ▸); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: Mercury (Macrae et al., 2008 ▸); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015 ▸). Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989015006970/hb7399sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015006970/hb7399Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S2056989015006970/hb7399Isup3.cml Click here for additional data file. . DOI: 10.1107/S2056989015006970/hb7399fig1.tif The molecular structure of the title compound, showing displacement ellipsoids drawn at the 50% probability level. Click here for additional data file. a . DOI: 10.1107/S2056989015006970/hb7399fig2.tif The packing of (I) showing grid like structure when viewed along a axis. Click here for additional data file. a . DOI: 10.1107/S2056989015006970/hb7399fig3.tif The packing of (I) showing C—H⋯π interactions when viewed along a axis. Click here for additional data file. . DOI: 10.1107/S2056989015006970/hb7399fig4.tif The formation of the title compound. CCDC reference: 1058259 Additional supporting information: crystallographic information; 3D view; checkCIF report

C₁₇H₁₂O₅	D_x = 1.460 Mg m⁻³
M_r = 296.27	Melting point: 435 K
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
a = 6.2648 (18) Å	Cell parameters from 2385 reflections
b = 10.435 (3) Å	θ = 2.0–25.0°
c = 20.621 (7) Å	µ = 0.11 mm⁻¹
V = 1348.0 (7) Å³	T = 296 K
Z = 4	Prism, colourless
F(000) = 616	0.22 × 0.20 × 0.18 mm
prism

Bruker APEXII CCD diffractometer	2385 independent reflections
Radiation source: fine-focus sealed tube	2150 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
Detector resolution: 2.01 pixels mm^-1	θ_max = 25.0°, θ_min = 2.0°
phi and ω scans	h = −7→5
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −12→12
T_min = 0.977, T_max = 0.981	l = −24→23
10472 measured reflections

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.035	H-atom parameters constrained
wR(F²) = 0.085	w = 1/[σ²(F_o²) + (0.0342P)² + 0.2933P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
1411 reflections	Δρ_max = 0.16 e Å⁻³
201 parameters	Δρ_min = −0.16 e Å⁻³
0 restraints	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 constraints	Extinction coefficient: 0.010 (3)
Primary atom site location: structure-invariant direct methods

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
O5	0.2218 (3)	0.80557 (17)	0.42819 (9)	0.0181 (5)
O4	0.5756 (3)	0.70623 (17)	0.18810 (9)	0.0213 (5)
O1	1.0215 (3)	0.54316 (17)	0.02385 (9)	0.0172 (5)
O2	1.1382 (3)	0.53880 (19)	0.12431 (9)	0.0221 (5)
O3	0.8203 (3)	0.56290 (18)	0.22324 (9)	0.0216 (5)
C17	0.0344 (5)	0.7406 (3)	0.44957 (15)	0.0235 (7)
H17A	−0.0827	0.7619	0.4215	0.035*
H17B	0.0014	0.7664	0.4931	0.035*
H17C	0.0584	0.6497	0.4484	0.035*
C14	0.3033 (5)	0.7725 (2)	0.36853 (13)	0.0146 (6)
C13	0.1987 (5)	0.6954 (2)	0.32378 (13)	0.0185 (6)
H13	0.0656	0.6606	0.3333	0.022*
C12	0.2960 (5)	0.6709 (2)	0.26457 (14)	0.0195 (7)
H12	0.2284	0.6191	0.2341	0.023*
C11	0.4914 (5)	0.7230 (2)	0.25097 (13)	0.0189 (6)
C10	0.7332 (4)	0.6180 (2)	0.17961 (14)	0.0164 (6)
C8	0.7751 (4)	0.6021 (2)	0.10923 (13)	0.0143 (6)
C9	0.9873 (5)	0.5583 (2)	0.08977 (13)	0.0153 (6)
C1	0.8638 (5)	0.5612 (2)	−0.02156 (13)	0.0155 (6)
C2	0.9148 (5)	0.5377 (2)	−0.08562 (14)	0.0204 (7)
H2	1.0497	0.5080	−0.0969	0.024*
C3	0.7610 (5)	0.5592 (3)	−0.13272 (14)	0.0223 (7)
H3	0.7935	0.5448	−0.1761	0.027*
C7	0.6224 (5)	0.6229 (2)	0.06469 (13)	0.0148 (6)
H7	0.4887	0.6511	0.0781	0.018*
C6	0.6609 (4)	0.6025 (2)	−0.00282 (13)	0.0153 (6)
C5	0.5082 (5)	0.6226 (2)	−0.05175 (13)	0.0181 (6)
H5	0.3717	0.6500	−0.0407	0.022*
C4	0.5591 (5)	0.6021 (3)	−0.11558 (14)	0.0204 (7)
H4	0.4575	0.6169	−0.1476	0.024*
C15	0.5015 (5)	0.8245 (2)	0.35439 (13)	0.0173 (6)
H15	0.5705	0.8756	0.3849	0.021*
C16	0.5972 (5)	0.8008 (3)	0.29511 (14)	0.0187 (7)
H16	0.7294	0.8361	0.2851	0.022*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O5	0.0178 (11)	0.0206 (9)	0.0160 (11)	−0.0012 (9)	0.0043 (8)	−0.0010 (8)
O4	0.0249 (12)	0.0249 (10)	0.0140 (11)	0.0105 (9)	0.0029 (8)	0.0000 (8)
O1	0.0158 (11)	0.0205 (9)	0.0154 (11)	0.0007 (9)	0.0018 (8)	−0.0017 (8)
O2	0.0175 (12)	0.0299 (11)	0.0189 (11)	0.0057 (9)	−0.0032 (9)	−0.0045 (8)
O3	0.0218 (12)	0.0276 (10)	0.0153 (11)	0.0042 (10)	−0.0001 (9)	0.0035 (8)
C17	0.0247 (19)	0.0205 (14)	0.0252 (17)	−0.0036 (13)	0.0078 (14)	0.0008 (12)
C14	0.0177 (16)	0.0133 (12)	0.0128 (15)	0.0039 (12)	0.0004 (12)	0.0022 (10)
C13	0.0173 (16)	0.0183 (13)	0.0198 (16)	0.0002 (13)	−0.0019 (13)	0.0006 (12)
C12	0.0230 (18)	0.0187 (14)	0.0169 (16)	0.0033 (13)	−0.0034 (13)	−0.0039 (11)
C11	0.0223 (17)	0.0198 (14)	0.0146 (15)	0.0070 (13)	0.0012 (12)	0.0007 (12)
C10	0.0139 (16)	0.0148 (13)	0.0204 (17)	−0.0021 (12)	0.0000 (13)	0.0012 (12)
C8	0.0154 (16)	0.0114 (12)	0.0163 (15)	−0.0017 (11)	0.0004 (12)	−0.0005 (11)
C9	0.0195 (17)	0.0125 (12)	0.0138 (15)	−0.0008 (12)	0.0019 (13)	−0.0013 (10)
C1	0.0186 (17)	0.0118 (12)	0.0162 (15)	−0.0028 (12)	−0.0013 (12)	0.0016 (11)
C2	0.0233 (17)	0.0151 (13)	0.0228 (17)	−0.0018 (12)	0.0056 (13)	−0.0018 (12)
C3	0.034 (2)	0.0186 (13)	0.0145 (16)	−0.0064 (13)	0.0031 (14)	−0.0009 (12)
C7	0.0135 (16)	0.0108 (12)	0.0202 (17)	−0.0005 (11)	0.0021 (12)	−0.0003 (11)
C6	0.0183 (17)	0.0097 (11)	0.0178 (16)	−0.0030 (12)	0.0017 (13)	0.0010 (11)
C5	0.0211 (17)	0.0127 (13)	0.0206 (16)	0.0006 (12)	−0.0020 (14)	0.0011 (11)
C4	0.0298 (19)	0.0143 (13)	0.0171 (16)	−0.0027 (13)	−0.0056 (13)	0.0017 (11)
C15	0.0188 (16)	0.0143 (12)	0.0189 (15)	−0.0001 (12)	−0.0030 (13)	−0.0019 (11)
C16	0.0125 (15)	0.0220 (14)	0.0216 (16)	0.0013 (12)	0.0020 (12)	0.0013 (12)

O5—C14	1.376 (3)	C10—C8	1.484 (4)
O5—C17	1.426 (3)	C8—C7	1.344 (4)
O4—C10	1.361 (3)	C8—C9	1.462 (4)
O4—C11	1.411 (3)	C1—C2	1.381 (4)
O1—C1	1.374 (3)	C1—C6	1.397 (4)
O1—C9	1.385 (3)	C2—C3	1.386 (4)
O2—C9	1.201 (3)	C2—H2	0.9300
O3—C10	1.199 (3)	C3—C4	1.388 (4)
C17—H17A	0.9600	C3—H3	0.9300
C17—H17B	0.9600	C7—C6	1.429 (4)
C17—H17C	0.9600	C7—H7	0.9300
C14—C15	1.386 (4)	C6—C5	1.406 (4)
C14—C13	1.389 (4)	C5—C4	1.371 (4)
C13—C12	1.388 (4)	C5—H5	0.9300
C13—H13	0.9300	C4—H4	0.9300
C12—C11	1.368 (4)	C15—C16	1.384 (4)
C12—H12	0.9300	C15—H15	0.9300
C11—C16	1.388 (4)	C16—H16	0.9300

C14—O5—C17	117.6 (2)	O1—C9—C8	116.5 (2)
C10—O4—C11	118.2 (2)	O1—C1—C2	117.5 (3)
C1—O1—C9	122.8 (2)	O1—C1—C6	120.5 (2)
O5—C17—H17A	109.5	C2—C1—C6	122.0 (3)
O5—C17—H17B	109.5	C1—C2—C3	118.7 (3)
H17A—C17—H17B	109.5	C1—C2—H2	120.6
O5—C17—H17C	109.5	C3—C2—H2	120.6
H17A—C17—H17C	109.5	C2—C3—C4	120.5 (3)
H17B—C17—H17C	109.5	C2—C3—H3	119.8
O5—C14—C15	115.0 (2)	C4—C3—H3	119.8
O5—C14—C13	124.4 (3)	C8—C7—C6	121.4 (3)
C15—C14—C13	120.7 (3)	C8—C7—H7	119.3
C12—C13—C14	118.9 (3)	C6—C7—H7	119.3
C12—C13—H13	120.5	C1—C6—C5	117.8 (3)
C14—C13—H13	120.5	C1—C6—C7	118.0 (3)
C11—C12—C13	120.0 (3)	C5—C6—C7	124.2 (3)
C11—C12—H12	120.0	C4—C5—C6	120.5 (3)
C13—C12—H12	120.0	C4—C5—H5	119.8
C12—C11—C16	121.7 (3)	C6—C5—H5	119.8
C12—C11—O4	118.3 (3)	C5—C4—C3	120.5 (3)
C16—C11—O4	119.8 (3)	C5—C4—H4	119.8
O3—C10—O4	123.9 (3)	C3—C4—H4	119.8
O3—C10—C8	126.8 (3)	C16—C15—C14	120.2 (3)
O4—C10—C8	109.2 (2)	C16—C15—H15	119.9
C7—C8—C9	120.7 (3)	C14—C15—H15	119.9
C7—C8—C10	121.6 (3)	C15—C16—C11	118.5 (3)
C9—C8—C10	117.7 (2)	C15—C16—H16	120.7
O2—C9—O1	116.2 (3)	C11—C16—H16	120.7
O2—C9—C8	127.3 (3)

C17—O5—C14—C15	−170.9 (2)	C9—O1—C1—C6	3.2 (3)
C17—O5—C14—C13	10.3 (4)	O1—C1—C2—C3	−177.9 (2)
O5—C14—C13—C12	178.8 (2)	C6—C1—C2—C3	1.8 (4)
C15—C14—C13—C12	0.1 (4)	C1—C2—C3—C4	−0.8 (4)
C14—C13—C12—C11	−0.3 (4)	C9—C8—C7—C6	0.3 (4)
C13—C12—C11—C16	0.0 (4)	C10—C8—C7—C6	−177.4 (2)
C13—C12—C11—O4	−174.0 (2)	O1—C1—C6—C5	178.3 (2)
C10—O4—C11—C12	−103.6 (3)	C2—C1—C6—C5	−1.4 (4)
C10—O4—C11—C16	82.4 (3)	O1—C1—C6—C7	−1.1 (3)
C11—O4—C10—O3	−8.0 (4)	C2—C1—C6—C7	179.3 (2)
C11—O4—C10—C8	171.6 (2)	C8—C7—C6—C1	−0.6 (4)
O3—C10—C8—C7	151.7 (3)	C8—C7—C6—C5	−179.9 (2)
O4—C10—C8—C7	−27.9 (3)	C1—C6—C5—C4	0.0 (4)
O3—C10—C8—C9	−26.2 (4)	C7—C6—C5—C4	179.3 (2)
O4—C10—C8—C9	154.2 (2)	C6—C5—C4—C3	1.0 (4)
C1—O1—C9—O2	179.5 (2)	C2—C3—C4—C5	−0.6 (4)
C1—O1—C9—C8	−3.3 (3)	O5—C14—C15—C16	−178.4 (2)
C7—C8—C9—O2	178.4 (3)	C13—C14—C15—C16	0.5 (4)
C10—C8—C9—O2	−3.8 (4)	C14—C15—C16—C11	−0.8 (4)
C7—C8—C9—O1	1.6 (3)	C12—C11—C16—C15	0.6 (4)
C10—C8—C9—O1	179.4 (2)	O4—C11—C16—C15	174.4 (2)
C9—O1—C1—C2	−177.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17B···O5ⁱ	0.96	2.50	3.228 (3)	132
C12—H12···O2ⁱⁱ	0.93	2.48	3.353 (3)	156
C15—H15···O2ⁱⁱⁱ	0.93	2.50	3.207 (3)	133
C3—H3···O3^iv	0.93	2.47	3.272 (4)	145
C5—H5···Cg1^v	0.93	2.82	3.303 (3)	114
C17—H17C···Cg2^vi	0.93	2.96	3.709 (4)	136

Table 1

Hydrogen-bond geometry (, )

Cg1 and Cg2 are the centroids of the C1/C6/C7/C8/C9/O1 and C1/C2/C3/C4/C5/C6 rings, respectively.

DHA	DH	HA	D A	DHA
C17H17BO5ⁱ	0.96	2.50	3.228(3)	132
C12H12O2ⁱⁱ	0.93	2.48	3.353(3)	156
C15H15O2ⁱⁱⁱ	0.93	2.50	3.207(3)	133
C3H3O3^iv	0.93	2.47	3.272(4)	145
C5H5Cg1^v	0.93	2.82	3.303 (3)	114
C17H17C Cg2^vi	0.93	2.96	3.709 (4)	136

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

8 in total

1. Antimicrobial activity of new coumarin derivatives.

Authors: M Kawase; B Varu; A Shah; N Motohashi; S Tani; S Saito; S Debnath; S Mahapatra; S G Dastidar; A N Chakrabarty
Journal: Arzneimittelforschung Date: 2001-01

2. A short history of SHELX.

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

Review 3. Studies on coumarins and coumarin-related compounds to determine their therapeutic role in the treatment of cancer.

Authors: Aoife Lacy; Richard O'Kennedy
Journal: Curr Pharm Des Date: 2004 Impact factor: 3.116

Review 4. New synthetic routes to furocoumarins and their analogs: a review.

Authors: Valery F Traven
Journal: Molecules Date: 2004-02-28 Impact factor: 4.411

5. Synthesis, molecular modeling, and selective inhibitory activity against human monoamine oxidases of 3-carboxamido-7-substituted coumarins.

Authors: Franco Chimenti; Daniela Secci; Adriana Bolasco; Paola Chimenti; Bruna Bizzarri; Arianna Granese; Simone Carradori; Matilde Yáñez; Francisco Orallo; Francesco Ortuso; Stefano Alcaro
Journal: J Med Chem Date: 2009-04-09 Impact factor: 7.446