3-[1-(2-Hy-droxy-anilino)ethyl-idene]-3H-chromen-2,4-dione.

The title compound is a new amino-coumarin derivative, C17H13NO4, and was synthesized by the condensation of 2-amino-phenol and 3-acetyl-4-hy-droxy-coumarin. An intra-molecular N-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, the molecules are linked into chains extending in the [010] direction by O-H⋯O hydrogen bonds. There is also a π-π stacking inter-action between the bicyclic coumarin fragment and the phenol ring [centroid-centroid distance = 3.7510 (14) Å], and these ring systems form between them a dihedral angle of 53.3 (2)°. Intermolecular hydrogen bond C-H⋯O hydrogen bonding is also observed in the interconnection of the crystal packing.

Related literature

For related structures, see: Traven et al. (2000 ▶); Malecka et al. (2004 ▶); Mechi et al. (2009 ▶); Ghouili et al. (2011 ▶); Ketata et al. (2012 ▶). For the properties of coumarin derivatives, see: Bordin et al. (1995 ▶); Hamdi et al. (2010 ▶); Mahidol et al. (2004 ▶).

Experimental

Crystal data

C17H13NO4

M = 295.29

Monoclinic,

a = 12.5596 (4) Å

b = 7.5870 (3) Å

c = 14.3433 (6) Å

β = 94.660 (2)°

V = 1362.25 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.16 × 0.13 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

11784 measured reflections

3891 independent reflections

1721 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.194

S = 0.91

3891 reflections

251 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SMART; data reduction: SAINT (Bruker, 2001 ▶); 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, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681301934X/ff2111sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681301934X/ff2111Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681301934X/ff2111Isup3.cml

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

C17H13NO4	F(000) = 616
Mr = 295.29	Dx = 1.440 Mg m−3
Monoclinic, P21/n	Melting point: 446 K
Hall symbol: -P2yn	Mo Kα radiation, λ = 0.71073 Å
a = 12.5596 (4) Å	Cell parameters from 1721 reflections
b = 7.5870 (3) Å	µ = 0.10 mm−1
c = 14.3433 (6) Å	T = 293 K
β = 94.660 (2)°	Needle, yellow
V = 1362.25 (9) Å3	0.16 × 0.13 × 0.10 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1721 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.053
Graphite monochromator	θmax = 29.8°, θmin = 2.1°
φ and ω scans	h = −14→17
11784 measured reflections	k = −9→10
3891 independent reflections	l = −19→20

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.194	H atoms treated by a mixture of independent and constrained refinement
S = 0.91	w = 1/[σ2(Fo2) + (0.0922P)2 + 0.2201P] where P = (Fo2 + 2Fc2)/3
3891 reflections	(Δ/σ)max < 0.001
251 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

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.

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	Uiso*/Ueq
O1	0.12600 (13)	0.1466 (2)	0.90032 (12)	0.0480 (5)
N1	0.22554 (16)	0.0473 (3)	1.22516 (14)	0.0375 (5)
C1	0.17836 (17)	0.0955 (3)	1.06478 (16)	0.0350 (5)
O3	0.34691 (12)	−0.0400 (2)	1.09988 (12)	0.0484 (5)
C2	0.27686 (18)	0.0180 (3)	1.04068 (17)	0.0378 (6)
C3	0.29714 (18)	0.0128 (3)	0.94130 (17)	0.0389 (6)
C4	0.21353 (18)	0.0298 (3)	1.32227 (17)	0.0368 (6)
O4	0.38154 (13)	0.1659 (2)	1.35092 (12)	0.0473 (5)
H12	0.4244	0.1965	1.3941	0.071*
C5	0.15554 (17)	0.1107 (3)	1.16048 (17)	0.0363 (6)
O2	0.01364 (14)	0.2201 (3)	1.00033 (13)	0.0556 (5)
C6	0.29532 (19)	0.0900 (3)	1.38614 (18)	0.0376 (6)
C7	0.22130 (19)	0.0795 (3)	0.87552 (18)	0.0417 (6)
C8	0.2850 (2)	0.0704 (3)	1.48055 (18)	0.0439 (6)
H4	0.3384	0.1118	1.5238	0.053*
C9	0.05868 (19)	0.2032 (4)	1.19047 (19)	0.0475 (7)
H5	0.0586	0.1977	1.2573	0.071*
H11	−0.0045	0.1470	1.1623	0.071*
H7	0.0598	0.3242	1.1710	0.071*
C10	0.2392 (2)	0.0838 (4)	0.78132 (19)	0.0546 (7)
H10	0.1871	0.1274	0.7375	0.065*
C11	0.10187 (19)	0.1569 (3)	0.99164 (18)	0.0416 (6)
C12	0.3922 (2)	−0.0510 (3)	0.9114 (2)	0.0481 (7)
H1	0.4431	−0.0990	0.9548	0.058*
C13	0.12623 (19)	−0.0559 (3)	1.35386 (19)	0.0451 (7)
H2	0.0735	−0.1007	1.3111	0.054*
C14	0.1168 (2)	−0.0752 (4)	1.4483 (2)	0.0503 (7)
H3	0.0575	−0.1314	1.4695	0.060*
C15	0.4121 (2)	−0.0446 (4)	0.8187 (2)	0.0545 (7)
H8	0.4768	−0.0848	0.7996	0.065*
C16	0.1960 (2)	−0.0104 (4)	1.51091 (19)	0.0497 (7)
H6	0.1893	−0.0214	1.5747	0.060*
C17	0.3343 (2)	0.0230 (4)	0.7537 (2)	0.0583 (8)
H9	0.3471	0.0268	0.6908	0.070*
H13	0.283 (2)	0.007 (4)	1.201 (2)	0.061 (9)*

	U11	U22	U33	U12	U13	U23
O1	0.0451 (10)	0.0600 (12)	0.0366 (10)	0.0120 (9)	−0.0099 (8)	0.0012 (9)
N1	0.0327 (11)	0.0452 (12)	0.0330 (11)	0.0007 (9)	−0.0072 (9)	−0.0010 (9)
C1	0.0327 (11)	0.0370 (13)	0.0335 (13)	0.0004 (10)	−0.0089 (10)	0.0011 (10)
O3	0.0378 (9)	0.0621 (12)	0.0433 (10)	0.0091 (8)	−0.0085 (8)	0.0041 (9)
C2	0.0347 (12)	0.0368 (13)	0.0398 (13)	−0.0011 (10)	−0.0104 (10)	0.0017 (11)
C3	0.0387 (13)	0.0355 (13)	0.0413 (14)	−0.0040 (11)	−0.0045 (11)	−0.0031 (11)
C4	0.0355 (12)	0.0391 (13)	0.0342 (13)	0.0009 (10)	−0.0057 (10)	−0.0007 (11)
O4	0.0390 (9)	0.0621 (12)	0.0390 (10)	−0.0135 (8)	−0.0080 (8)	0.0009 (9)
C5	0.0339 (12)	0.0330 (13)	0.0403 (14)	−0.0055 (10)	−0.0082 (10)	−0.0012 (10)
O2	0.0406 (10)	0.0748 (14)	0.0484 (11)	0.0151 (9)	−0.0141 (8)	0.0016 (10)
C6	0.0403 (13)	0.0340 (13)	0.0375 (13)	−0.0002 (10)	−0.0032 (10)	−0.0001 (11)
C7	0.0436 (14)	0.0406 (14)	0.0393 (14)	−0.0002 (11)	−0.0069 (11)	−0.0026 (11)
C8	0.0474 (14)	0.0477 (16)	0.0351 (14)	−0.0028 (12)	−0.0063 (11)	−0.0026 (12)
C9	0.0409 (13)	0.0541 (17)	0.0462 (16)	0.0054 (12)	−0.0047 (12)	−0.0015 (13)
C10	0.0630 (18)	0.0593 (18)	0.0395 (16)	0.0063 (15)	−0.0078 (13)	0.0033 (13)
C11	0.0399 (13)	0.0428 (15)	0.0400 (15)	−0.0012 (12)	−0.0094 (11)	0.0003 (12)
C12	0.0413 (13)	0.0493 (16)	0.0519 (17)	0.0012 (12)	−0.0073 (12)	−0.0047 (13)
C13	0.0377 (13)	0.0486 (16)	0.0475 (16)	−0.0029 (11)	−0.0056 (12)	−0.0019 (12)
C14	0.0471 (15)	0.0493 (16)	0.0554 (18)	−0.0022 (12)	0.0104 (13)	0.0016 (14)
C15	0.0489 (15)	0.0655 (19)	0.0492 (17)	−0.0035 (14)	0.0040 (13)	−0.0079 (15)
C16	0.0601 (17)	0.0510 (16)	0.0384 (14)	0.0040 (14)	0.0057 (13)	0.0006 (13)
C17	0.0656 (18)	0.067 (2)	0.0427 (16)	−0.0056 (16)	0.0035 (14)	−0.0031 (15)

O1—C7	1.374 (3)	C7—C10	1.388 (4)
O1—C11	1.370 (3)	C8—C16	1.376 (4)
N1—C5	1.316 (3)	C8—H4	0.9300
N1—C4	1.419 (3)	C9—H5	0.9600
N1—H13	0.88 (3)	C9—H11	0.9600
C1—C5	1.429 (3)	C9—H7	0.9600
C1—C2	1.437 (3)	C10—C17	1.369 (4)
C1—C11	1.441 (3)	C10—H10	0.9300
O3—C2	1.252 (3)	C12—C15	1.373 (4)
C2—C3	1.469 (3)	C12—H1	0.9300
C3—C7	1.381 (3)	C13—C14	1.376 (4)
C3—C12	1.388 (3)	C13—H2	0.9300
C4—C13	1.382 (3)	C14—C16	1.376 (4)
C4—C6	1.396 (3)	C14—H3	0.9300
O4—C6	1.359 (3)	C15—C17	1.393 (4)
O4—H12	0.8200	C15—H8	0.9300
C5—C9	1.498 (3)	C16—H6	0.9300
O2—C11	1.223 (3)	C17—H9	0.9300
C6—C8	1.379 (3)
C7—O1—C11	122.26 (19)	C5—C9—H11	109.5
C5—N1—C4	127.4 (2)	H5—C9—H11	109.5
C5—N1—H13	112 (2)	C5—C9—H7	109.5
C4—N1—H13	121 (2)	H5—C9—H7	109.5
C5—C1—C2	120.5 (2)	H11—C9—H7	109.5
C5—C1—C11	119.9 (2)	C17—C10—C7	119.2 (3)
C2—C1—C11	119.6 (2)	C17—C10—H10	120.4
O3—C2—C1	123.5 (2)	C7—C10—H10	120.4
O3—C2—C3	118.8 (2)	O2—C11—O1	113.1 (2)
C1—C2—C3	117.7 (2)	O2—C11—C1	127.5 (2)
C7—C3—C12	118.6 (2)	O1—C11—C1	119.4 (2)
C7—C3—C2	119.3 (2)	C15—C12—C3	121.0 (3)
C12—C3—C2	122.0 (2)	C15—C12—H1	119.5
C13—C4—C6	120.0 (2)	C3—C12—H1	119.5
C13—C4—N1	121.1 (2)	C4—C13—C14	120.4 (2)
C6—C4—N1	118.8 (2)	C4—C13—H2	119.8
C6—O4—H12	109.5	C14—C13—H2	119.8
N1—C5—C1	118.2 (2)	C13—C14—C16	119.3 (2)
N1—C5—C9	118.7 (2)	C13—C14—H3	120.4
C1—C5—C9	123.0 (2)	C16—C14—H3	120.4
O4—C6—C8	123.5 (2)	C12—C15—C17	119.3 (3)
O4—C6—C4	117.4 (2)	C12—C15—H8	120.4
C8—C6—C4	119.1 (2)	C17—C15—H8	120.4
O1—C7—C3	121.7 (2)	C8—C16—C14	121.0 (3)
O1—C7—C10	117.2 (2)	C8—C16—H6	119.5
C3—C7—C10	121.1 (2)	C14—C16—H6	119.5
C6—C8—C16	120.1 (2)	C10—C17—C15	120.7 (3)
C6—C8—H4	119.9	C10—C17—H9	119.6
C16—C8—H4	119.9	C15—C17—H9	119.6
C5—C9—H5	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O4—H12···O2i	0.82	1.92	2.742 (2)	175
N1—H13···O3	0.88 (3)	1.75 (3)	2.537 (3)	148 (3)
C8—H4···O2i	0.93	2.59	3.274 (3)	131

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H12⋯O2i	0.82	1.92	2.742 (2)	175
N1—H13⋯O3	0.88 (3)	1.75 (3)	2.537 (3)	148 (3)
C8—H4⋯O2i	0.93	2.59	3.274 (3)	131

Symmetry code: (i) .