Ethyl 4-(2-fur-yl)-2-oxochroman-3-carboxyl-ate.

The title compound, C(16)H(14)O(5), was prepared from the reaction of 3-carbethoxy-coumarin with furan in the presence of AlCl(3) as catalyst. In the crystal, inter-molecular C-H⋯O hydrogen-bonding inter-actions between four mol-ecules lead to a tetra-mer in the unit cell. The furan ring is anti-periplanar [C-C-C-O = 167.9 (13)°] and the ethoxy-carbonyl group is (-)anti-clinal [C-C-C-O = -128.6 (14)°] to the lactone ring.

Related literature

For the medicinal and biological activity of coumarins and their derivatives, see: Borges et al. (2005 ▶); Kontogiorgis & Hadjipavlou-Litina (2005 ▶); Gursoy & Karali (2003 ▶); Prabhakar et al. (2010 ▶). For the assignment of conformations and the orientation of the substituents, see: Nardelli (1983 ▶, 1995 ▶); Klyne & Prelog (1960 ▶).

Experimental

Crystal data

C16H14O5

M = 286.27

Monoclinic,

a = 10.393 (3) Å

b = 8.459 (3) Å

c = 15.819 (5) Å

β = 95.464 (5)°

V = 1384.5 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.34 × 0.24 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2003 ▶) T min = 0.966, T max = 0.980

13767 measured reflections

2711 independent reflections

2099 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.111

S = 1.04

2711 reflections

227 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810016193/ds2028sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016193/ds2028Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H14O5	F(000) = 600
Mr = 286.27	Dx = 1.373 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5174 reflections
a = 10.393 (3) Å	θ = 2.5–25.8°
b = 8.459 (3) Å	µ = 0.10 mm−1
c = 15.819 (5) Å	T = 298 K
β = 95.464 (5)°	Block, colourless
V = 1384.5 (8) Å3	0.34 × 0.24 × 0.20 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2711 independent reflections
Radiation source: fine-focus sealed tube	2099 reflections with I > 2σ(I)
graphite	Rint = 0.035
phi and ω scans	θmax = 25.9°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −12→12
Tmin = 0.966, Tmax = 0.980	k = −10→10
13767 measured reflections	l = −19→19

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.058P)2 + 0.1619P] where P = (Fo2 + 2Fc2)/3
2711 reflections	(Δ/σ)max < 0.001
227 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.15 e Å−3

	x	y	z	Uiso*/Ueq
H2	0.5893 (16)	0.9788 (19)	0.7769 (10)	0.045 (4)*
H13	0.648 (2)	1.325 (3)	1.0884 (14)	0.084 (7)*
H11	0.598 (2)	1.251 (2)	0.8313 (14)	0.076 (6)*
H12	0.598 (2)	1.472 (3)	0.9435 (13)	0.081 (6)*
H7	1.082 (2)	0.672 (3)	1.0318 (14)	0.085 (7)*
H6	0.8933 (19)	0.630 (2)	1.0962 (13)	0.073 (6)*
H8	1.077 (2)	0.828 (2)	0.9093 (13)	0.078 (6)*
H5	0.6973 (18)	0.7462 (19)	1.0400 (11)	0.048 (5)*
H3	0.5753 (15)	0.8783 (17)	0.9186 (9)	0.033 (4)*
C6	0.8921 (2)	0.6956 (2)	1.04771 (12)	0.0626 (5)
O3	0.65502 (12)	1.13244 (14)	1.01627 (7)	0.0545 (3)
O1	0.88812 (11)	0.98037 (14)	0.83531 (7)	0.0523 (3)
O5	0.74734 (13)	0.71312 (14)	0.73664 (7)	0.0598 (4)
O2	0.78518 (13)	1.08381 (15)	0.72090 (7)	0.0635 (4)
C3	0.65067 (15)	0.93666 (18)	0.90397 (9)	0.0404 (4)
O4	0.57089 (13)	0.66307 (15)	0.80304 (8)	0.0651 (4)
C4	0.77275 (15)	0.86004 (17)	0.94453 (9)	0.0388 (4)
C1	0.77894 (17)	1.00313 (19)	0.78254 (10)	0.0460 (4)
C9	0.88546 (15)	0.88312 (18)	0.90688 (10)	0.0429 (4)
C2	0.65772 (16)	0.92533 (19)	0.80739 (10)	0.0425 (4)
C14	0.65204 (17)	0.7516 (2)	0.78227 (10)	0.0465 (4)
C13	0.63873 (19)	1.2923 (2)	1.02691 (14)	0.0597 (5)
C8	1.00056 (18)	0.8154 (2)	0.93811 (12)	0.0576 (5)
C5	0.77720 (19)	0.7640 (2)	1.01532 (10)	0.0502 (4)
C10	0.63742 (14)	1.10518 (19)	0.93083 (9)	0.0419 (4)
C11	0.61161 (18)	1.2410 (2)	0.89003 (12)	0.0550 (5)
C12	0.61250 (19)	1.3618 (2)	0.95281 (13)	0.0593 (5)
C15	0.7673 (2)	0.5456 (2)	0.71929 (12)	0.0718 (6)
H15A	0.8029	0.5339	0.6652	0.086*
H15B	0.6853	0.4902	0.7162	0.086*
C7	1.0035 (2)	0.7225 (2)	1.00924 (13)	0.0656 (5)
C16	0.8571 (2)	0.4771 (2)	0.78765 (14)	0.0738 (6)
H16A	0.9356	0.5376	0.7935	0.111*
H16B	0.8763	0.3698	0.7737	0.111*
H16C	0.8177	0.4795	0.8401	0.111*

	U11	U22	U33	U12	U13	U23
C6	0.0812 (15)	0.0569 (11)	0.0475 (10)	0.0109 (10)	−0.0047 (10)	0.0124 (9)
O3	0.0658 (8)	0.0534 (7)	0.0449 (7)	0.0049 (6)	0.0093 (5)	−0.0084 (5)
O1	0.0463 (7)	0.0581 (7)	0.0526 (7)	−0.0034 (5)	0.0059 (5)	0.0137 (6)
O5	0.0819 (9)	0.0466 (7)	0.0524 (7)	0.0094 (6)	0.0151 (7)	−0.0060 (5)
O2	0.0824 (9)	0.0614 (8)	0.0474 (7)	0.0061 (7)	0.0110 (6)	0.0171 (6)
C3	0.0377 (8)	0.0423 (9)	0.0416 (8)	−0.0022 (7)	0.0052 (7)	−0.0030 (7)
O4	0.0666 (8)	0.0592 (8)	0.0684 (9)	−0.0165 (7)	0.0007 (7)	−0.0116 (6)
C4	0.0459 (9)	0.0342 (8)	0.0357 (8)	−0.0005 (6)	0.0000 (6)	−0.0043 (6)
C1	0.0571 (10)	0.0409 (9)	0.0403 (9)	0.0072 (7)	0.0058 (8)	0.0004 (7)
C9	0.0453 (9)	0.0417 (8)	0.0410 (8)	−0.0012 (7)	0.0005 (7)	0.0016 (7)
C2	0.0446 (9)	0.0423 (9)	0.0392 (8)	0.0078 (7)	−0.0041 (7)	−0.0021 (7)
C14	0.0539 (10)	0.0482 (9)	0.0352 (8)	0.0012 (8)	−0.0077 (7)	−0.0034 (7)
C13	0.0629 (12)	0.0556 (11)	0.0622 (12)	−0.0001 (9)	0.0144 (10)	−0.0197 (10)
C8	0.0456 (10)	0.0652 (12)	0.0609 (11)	0.0047 (8)	−0.0008 (9)	0.0030 (9)
C5	0.0623 (11)	0.0471 (10)	0.0420 (9)	−0.0002 (8)	0.0081 (8)	0.0010 (8)
C10	0.0384 (8)	0.0479 (9)	0.0394 (8)	0.0024 (7)	0.0044 (6)	−0.0057 (7)
C11	0.0628 (12)	0.0512 (10)	0.0508 (11)	0.0106 (8)	0.0039 (9)	−0.0008 (9)
C12	0.0629 (12)	0.0441 (10)	0.0723 (13)	0.0059 (9)	0.0138 (10)	−0.0066 (9)
C15	0.1093 (17)	0.0474 (11)	0.0597 (12)	0.0141 (11)	0.0133 (12)	−0.0108 (9)
C7	0.0622 (13)	0.0673 (13)	0.0641 (12)	0.0171 (10)	−0.0104 (10)	0.0071 (10)
C16	0.0813 (15)	0.0552 (11)	0.0863 (15)	0.0111 (10)	0.0158 (12)	0.0064 (11)

C6—C7	1.377 (3)	C2—C14	1.522 (2)
C6—C5	1.381 (3)	C2—H2	0.937 (17)
C6—H6	0.94 (2)	C13—C12	1.317 (3)
O3—C10	1.3663 (19)	C13—H13	1.01 (2)
O3—C13	1.375 (2)	C8—C7	1.371 (3)
O1—C1	1.357 (2)	C8—H8	0.96 (2)
O1—C9	1.4020 (19)	C5—H5	0.962 (18)
O5—C14	1.321 (2)	C10—C11	1.333 (2)
O5—C15	1.462 (2)	C11—C12	1.425 (3)
O2—C1	1.1969 (19)	C11—H11	0.93 (2)
C3—C10	1.498 (2)	C12—H12	0.95 (2)
C3—C4	1.512 (2)	C15—C16	1.478 (3)
C3—C2	1.539 (2)	C15—H15A	0.9700
C3—H3	0.972 (15)	C15—H15B	0.9700
O4—C14	1.197 (2)	C7—H7	0.95 (2)
C4—C9	1.378 (2)	C16—H16A	0.9600
C4—C5	1.381 (2)	C16—H16B	0.9600
C1—C2	1.506 (2)	C16—H16C	0.9600
C9—C8	1.375 (2)
C7—C6—C5	120.05 (18)	O3—C13—H13	113.0 (13)
C7—C6—H6	120.5 (13)	C7—C8—C9	118.97 (19)
C5—C6—H6	119.4 (13)	C7—C8—H8	119.9 (13)
C10—O3—C13	106.29 (14)	C9—C8—H8	121.0 (13)
C1—O1—C9	120.03 (12)	C6—C5—C4	120.55 (18)
C14—O5—C15	117.97 (15)	C6—C5—H5	122.2 (10)
C10—C3—C4	112.56 (13)	C4—C5—H5	117.2 (10)
C10—C3—C2	110.80 (13)	C11—C10—O3	109.59 (14)
C4—C3—C2	106.09 (12)	C11—C10—C3	134.68 (15)
C10—C3—H3	108.5 (8)	O3—C10—C3	115.73 (13)
C4—C3—H3	110.1 (8)	C10—C11—C12	107.06 (17)
C2—C3—H3	108.7 (8)	C10—C11—H11	124.6 (13)
C9—C4—C5	118.03 (15)	C12—C11—H11	128.3 (13)
C9—C4—C3	117.99 (13)	C13—C12—C11	106.68 (17)
C5—C4—C3	123.94 (15)	C13—C12—H12	126.2 (13)
O2—C1—O1	118.36 (16)	C11—C12—H12	127.1 (13)
O2—C1—C2	124.98 (16)	O5—C15—C16	109.51 (16)
O1—C1—C2	116.65 (13)	O5—C15—H15A	109.8
C8—C9—C4	122.14 (15)	C16—C15—H15A	109.8
C8—C9—O1	116.82 (15)	O5—C15—H15B	109.8
C4—C9—O1	121.02 (13)	C16—C15—H15B	109.8
C1—C2—C14	111.48 (13)	H15A—C15—H15B	108.2
C1—C2—C3	110.60 (13)	C8—C7—C6	120.24 (18)
C14—C2—C3	108.36 (13)	C8—C7—H7	120.9 (14)
C1—C2—H2	105.5 (10)	C6—C7—H7	118.8 (14)
C14—C2—H2	108.9 (10)	C15—C16—H16A	109.5
C3—C2—H2	112.1 (10)	C15—C16—H16B	109.5
O4—C14—O5	125.46 (16)	H16A—C16—H16B	109.5
O4—C14—C2	122.91 (16)	C15—C16—H16C	109.5
O5—C14—C2	111.62 (15)	H16A—C16—H16C	109.5
C12—C13—O3	110.37 (17)	H16B—C16—H16C	109.5
C12—C13—H13	136.6 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3i	0.972 (15)	2.696 (15)	3.576 (2)	150.8 (11)
C16—H16B···O2ii	0.96	2.70	3.549 (3)	148
C16—H16A···O2iii	0.96	2.96	3.841 (3)	153
C8—H8···O3iv	0.96 (2)	2.94 (2)	3.611 (3)	128.2 (15)
C11—H11···O4v	0.93 (2)	2.73 (2)	3.501 (3)	140.9 (17)
C13—H13···O2vi	1.01 (2)	2.54 (2)	3.456 (3)	151.0 (17)
C12—H12···O4vii	0.95 (2)	2.74 (2)	3.478 (3)	134.9 (16)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O3i	0.972 (15)	2.696 (15)	3.576 (2)	150.8 (11)
C16—H16B⋯O2ii	0.96	2.70	3.549 (3)	148
C16—H16A⋯O2iii	0.96	2.96	3.841 (3)	153
C8—H8⋯O3iv	0.96 (2)	2.94 (2)	3.611 (3)	128.2 (15)
C11—H11⋯O4v	0.93 (2)	2.73 (2)	3.501 (3)	140.9 (17)
C13—H13⋯O2vi	1.01 (2)	2.54 (2)	3.456 (3)	151.0 (17)
C12—H12⋯O4vii	0.95 (2)	2.74 (2)	3.478 (3)	134.9 (16)

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