4-{[Bis(2-hy-droxy-eth-yl)amino]-meth-yl}-6-meth-oxy-2H-chromen-2-one.

In the title compound, C(15)H(19)NO(5), an intra-molecular O-H⋯O hydrogen bond links the hy-droxy-ethyl side chains, forming a seven-membered ring. In the crystal, mol-ecules are linked into chains via O-H⋯O hydrogen bonds along the b axis. Further, mol-ecules are linked by weak inter-molecular C-H⋯O and π-π stacking inter-actions [centroid-centroid distance = 3.707 (4) Å].

Related literature

For the properties of coumarins, see: Meng et al. (1989 ▶); Baures et al. (2002 ▶); Jadhav et al. (2010 ▶); Basanagouda et al. (2011 ▶); Kokila et al. (1995 ▶); Khan et al. (2008 ▶). For 4-bromo­meth­yl-6-meth­oxy-2H-chromen-2-one, see: Basanagouda et al. (2011 ▶). For aromatic compounds containing a β-hy­droxy­ethyl side chain, see: Khan et al. (2008 ▶). For n class="Chemical">hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For C—H ⋯O inter­actions, see: Desiraju (2005 ▶). For stacking inter­actions, see: Janiak (2000 ▶). For related literature on 4-bromomethyl-2H-chromen-2-one, see: Basanagouda & Kulkarni (2011 ▶).

Experimental

Crystal data

C15H19NO5

M = 293.31

Monoclinic,

a = 9.3038 (5) Å

b = 7.9290 (5) Å

c = 19.6216 (12) Å

β = 92.944 (5)°

V = 1445.56 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 123 K

0.2 × 0.18 × 0.18 mm

Data collection

Bruker SMART APEX CCD detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.98, T max = 0.982

14012 measured reflections

2694 independent reflections

1994 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.149

S = 1.02

2694 reflections

194 parameters

H-atom parameters constrained

Δρmax = 0.51 e Å−3

Δρmin = −0.26 e Å−3

Data collection: SMART (Bruker, 2008 ▶); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 2008 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and CAMERON (Watkin et al., 1996 ▶); software used to prepare material for publication: PARST (Nardelli, 1995 ▶) and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812030759/zj2082sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812030759/zj2082Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812030759/zj2082Isup3.cml

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

C15H19NO5	F(000) = 624
Mr = 293.31	Dx = 1.348 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2837 reflections
a = 9.3038 (5) Å	θ = 2.8–29.6°
b = 7.9290 (5) Å	µ = 0.10 mm−1
c = 19.6216 (12) Å	T = 123 K
β = 92.944 (5)°	Block, white
V = 1445.56 (15) Å3	0.2 × 0.18 × 0.18 mm
Z = 4

Bruker SMART APEX CCD detector diffractometer	1994 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
ω scans	θmax = 25.5°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −11→11
Tmin = 0.98, Tmax = 0.982	k = −9→9
14012 measured reflections	l = −23→23
2694 independent 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)] = 0.053	H-atom parameters constrained
wR(F2) = 0.149	w = 1/[σ2(Fo2) + (0.0607P)2 + 0.6914P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2694 reflections	Δρmax = 0.51 e Å−3
194 parameters	Δρmin = −0.26 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0048 (14)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	0.6985 (3)	0.3637 (5)	0.38763 (14)	0.0794 (9)
H1A	0.6439	0.2862	0.3572	0.119*
H1B	0.7954	0.3787	0.3713	0.119*
H1C	0.6494	0.473	0.3881	0.119*
C2	0.5821 (2)	0.2628 (3)	0.48505 (12)	0.0478 (6)
C3	0.5966 (3)	0.1769 (3)	0.54703 (13)	0.0576 (7)
H3	0.6895	0.1449	0.5648	0.069*
C4	0.4789 (3)	0.1386 (3)	0.58220 (12)	0.0582 (7)
H4	0.4892	0.0812	0.6247	0.07*
C5	0.3436 (3)	0.1843 (3)	0.55550 (11)	0.0477 (6)
C6	0.0911 (3)	0.1865 (3)	0.57398 (13)	0.0587 (6)
C7	0.0712 (2)	0.2717 (3)	0.50921 (11)	0.0489 (6)
H7	−0.0241	0.2978	0.4929	0.059*
C8	0.1804 (2)	0.3160 (3)	0.47075 (10)	0.0384 (5)
C9	0.3255 (2)	0.2694 (3)	0.49382 (10)	0.0388 (5)
C10	0.4483 (2)	0.3085 (3)	0.45839 (11)	0.0403 (5)
H10	0.4391	0.3666	0.416	0.048*
C11	0.1511 (2)	0.4227 (3)	0.40816 (10)	0.0396 (5)
H11A	0.0465	0.446	0.4035	0.048*
H11B	0.2009	0.5322	0.4151	0.048*
C12	0.1882 (2)	0.4748 (3)	0.28977 (11)	0.0533 (6)
H12A	0.1148	0.5608	0.2994	0.064*
H12B	0.1587	0.419	0.2461	0.064*
C13	0.3309 (3)	0.5588 (3)	0.28329 (13)	0.0631 (7)
H13A	0.3242	0.6448	0.2467	0.076*
H13B	0.3614	0.6154	0.3266	0.076*
C14	0.1223 (2)	0.1916 (3)	0.32783 (12)	0.0512 (6)
H14A	0.0226	0.2163	0.3107	0.061*
H14B	0.1171	0.1226	0.3697	0.061*
C15	0.1966 (3)	0.0928 (4)	0.27525 (14)	0.0663 (7)
H15A	0.159	−0.024	0.2744	0.08*
H15B	0.1741	0.1433	0.2298	0.08*
N1	0.19564 (16)	0.3493 (2)	0.34476 (8)	0.0376 (4)
O1	0.2286 (2)	0.1440 (2)	0.59428 (8)	0.0618 (5)
O2	−0.0017 (2)	0.1540 (3)	0.61251 (10)	0.0857 (7)
O3	0.43185 (19)	0.4325 (3)	0.26743 (10)	0.0751 (6)
H3A	0.506	0.4782	0.2532	0.113*
O4	0.34542 (19)	0.0885 (3)	0.28742 (12)	0.0841 (7)
H4A	0.3776	0.1875	0.2893	0.126*
O5	0.70828 (16)	0.2960 (2)	0.45453 (9)	0.0662 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0469 (14)	0.131 (3)	0.0604 (17)	−0.0038 (16)	0.0068 (12)	−0.0128 (18)
C2	0.0422 (12)	0.0498 (13)	0.0503 (13)	0.0045 (10)	−0.0086 (10)	−0.0120 (11)
C3	0.0588 (15)	0.0521 (14)	0.0592 (15)	0.0117 (12)	−0.0228 (12)	−0.0096 (12)
C4	0.0791 (18)	0.0484 (14)	0.0449 (13)	0.0037 (12)	−0.0171 (12)	0.0041 (11)
C5	0.0628 (14)	0.0406 (12)	0.0396 (12)	−0.0014 (10)	0.0002 (10)	0.0000 (10)
C6	0.0666 (16)	0.0563 (15)	0.0544 (15)	−0.0097 (13)	0.0150 (13)	0.0012 (12)
C7	0.0491 (12)	0.0529 (13)	0.0453 (13)	−0.0036 (10)	0.0101 (10)	−0.0010 (11)
C8	0.0420 (11)	0.0376 (11)	0.0357 (11)	0.0003 (9)	0.0038 (8)	−0.0056 (9)
C9	0.0465 (12)	0.0340 (11)	0.0354 (11)	0.0012 (9)	−0.0014 (9)	−0.0043 (9)
C10	0.0416 (11)	0.0404 (11)	0.0383 (11)	0.0023 (9)	−0.0026 (9)	−0.0053 (9)
C11	0.0349 (10)	0.0443 (12)	0.0400 (11)	0.0048 (9)	0.0040 (8)	−0.0015 (9)
C12	0.0523 (13)	0.0653 (16)	0.0421 (12)	0.0122 (11)	0.0014 (10)	0.0114 (11)
C13	0.0777 (17)	0.0579 (16)	0.0551 (15)	−0.0041 (14)	0.0164 (13)	0.0162 (12)
C14	0.0431 (12)	0.0556 (14)	0.0556 (14)	−0.0050 (10)	0.0102 (10)	−0.0145 (11)
C15	0.0559 (15)	0.0741 (18)	0.0695 (17)	0.0041 (13)	0.0103 (12)	−0.0231 (15)
N1	0.0332 (8)	0.0461 (10)	0.0336 (9)	0.0010 (7)	0.0036 (7)	0.0016 (7)
O1	0.0804 (12)	0.0614 (11)	0.0441 (9)	−0.0060 (9)	0.0082 (8)	0.0127 (8)
O2	0.0929 (14)	0.0930 (16)	0.0747 (13)	−0.0181 (12)	0.0384 (11)	0.0192 (12)
O3	0.0592 (11)	0.0812 (14)	0.0872 (14)	−0.0104 (10)	0.0272 (10)	0.0099 (11)
O4	0.0599 (11)	0.0792 (14)	0.1143 (17)	0.0198 (10)	0.0140 (11)	−0.0294 (13)
O5	0.0376 (9)	0.0929 (14)	0.0672 (12)	0.0067 (9)	−0.0067 (8)	−0.0087 (10)

C1—O5	1.417 (3)	C10—H10	0.95
C1—H1A	0.98	C11—N1	1.453 (2)
C1—H1B	0.98	C11—H11A	0.99
C1—H1C	0.98	C11—H11B	0.99
C2—O5	1.370 (3)	C12—N1	1.467 (3)
C2—C10	1.374 (3)	C12—C13	1.497 (3)
C2—C3	1.394 (3)	C12—H12A	0.99
C3—C4	1.358 (4)	C12—H12B	0.99
C3—H3	0.95	C13—O3	1.419 (3)
C4—C5	1.386 (3)	C13—H13A	0.99
C4—H4	0.95	C13—H13B	0.99
C5—O1	1.382 (3)	C14—N1	1.455 (3)
C5—C9	1.388 (3)	C14—C15	1.493 (3)
C6—O2	1.204 (3)	C14—H14A	0.99
C6—O1	1.363 (3)	C14—H14B	0.99
C6—C7	1.443 (3)	C15—O4	1.393 (3)
C7—C8	1.343 (3)	C15—H15A	0.99
C7—H7	0.95	C15—H15B	0.99
C8—C9	1.450 (3)	O3—H3A	0.84
C8—C11	1.505 (3)	O4—H4A	0.84
C9—C10	1.402 (3)
O5—C1—H1A	109.5	C8—C11—H11A	108.5
O5—C1—H1B	109.5	N1—C11—H11B	108.5
H1A—C1—H1B	109.5	C8—C11—H11B	108.5
O5—C1—H1C	109.5	H11A—C11—H11B	107.5
H1A—C1—H1C	109.5	N1—C12—C13	110.84 (18)
H1B—C1—H1C	109.5	N1—C12—H12A	109.5
O5—C2—C10	124.2 (2)	C13—C12—H12A	109.5
O5—C2—C3	115.36 (19)	N1—C12—H12B	109.5
C10—C2—C3	120.4 (2)	C13—C12—H12B	109.5
C4—C3—C2	120.5 (2)	H12A—C12—H12B	108.1
C4—C3—H3	119.7	O3—C13—C12	107.7 (2)
C2—C3—H3	119.7	O3—C13—H13A	110.2
C3—C4—C5	119.3 (2)	C12—C13—H13A	110.2
C3—C4—H4	120.3	O3—C13—H13B	110.2
C5—C4—H4	120.3	C12—C13—H13B	110.2
O1—C5—C4	116.4 (2)	H13A—C13—H13B	108.5
O1—C5—C9	122.0 (2)	N1—C14—C15	112.37 (19)
C4—C5—C9	121.6 (2)	N1—C14—H14A	109.1
O2—C6—O1	117.1 (2)	C15—C14—H14A	109.1
O2—C6—C7	126.1 (3)	N1—C14—H14B	109.1
O1—C6—C7	116.7 (2)	C15—C14—H14B	109.1
C8—C7—C6	123.4 (2)	H14A—C14—H14B	107.9
C8—C7—H7	118.3	O4—C15—C14	112.7 (2)
C6—C7—H7	118.3	O4—C15—H15A	109.1
C7—C8—C9	118.5 (2)	C14—C15—H15A	109.1
C7—C8—C11	119.67 (19)	O4—C15—H15B	109.1
C9—C8—C11	121.66 (17)	C14—C15—H15B	109.1
C5—C9—C10	118.31 (19)	H15A—C15—H15B	107.8
C5—C9—C8	117.74 (19)	C11—N1—C14	112.88 (16)
C10—C9—C8	123.94 (19)	C11—N1—C12	110.68 (17)
C2—C10—C9	119.9 (2)	C14—N1—C12	114.28 (18)
C2—C10—H10	120.1	C6—O1—C5	121.58 (18)
C9—C10—H10	120.1	C13—O3—H3A	109.5
N1—C11—C8	115.19 (17)	C15—O4—H4A	109.5
N1—C11—H11A	108.5	C2—O5—C1	117.51 (17)
O5—C2—C3—C4	179.4 (2)	C5—C9—C10—C2	0.0 (3)
C10—C2—C3—C4	−0.6 (4)	C8—C9—C10—C2	178.38 (19)
C2—C3—C4—C5	0.7 (4)	C7—C8—C11—N1	−122.5 (2)
C3—C4—C5—O1	−179.1 (2)	C9—C8—C11—N1	62.1 (3)
C3—C4—C5—C9	−0.5 (4)	N1—C12—C13—O3	60.9 (3)
O2—C6—C7—C8	174.7 (3)	N1—C14—C15—O4	43.9 (3)
O1—C6—C7—C8	−3.0 (4)	C8—C11—N1—C14	61.4 (2)
C6—C7—C8—C9	2.9 (3)	C8—C11—N1—C12	−169.10 (17)
C6—C7—C8—C11	−172.6 (2)	C15—C14—N1—C11	−163.4 (2)
O1—C5—C9—C10	178.66 (19)	C15—C14—N1—C12	68.9 (3)
C4—C5—C9—C10	0.1 (3)	C13—C12—N1—C11	94.1 (2)
O1—C5—C9—C8	0.1 (3)	C13—C12—N1—C14	−137.1 (2)
C4—C5—C9—C8	−178.4 (2)	O2—C6—O1—C5	−176.4 (2)
C7—C8—C9—C5	−1.4 (3)	C7—C6—O1—C5	1.6 (3)
C11—C8—C9—C5	174.02 (19)	C4—C5—O1—C6	178.3 (2)
C7—C8—C9—C10	−179.8 (2)	C9—C5—O1—C6	−0.3 (3)
C11—C8—C9—C10	−4.4 (3)	C10—C2—O5—C1	−7.8 (3)
O5—C2—C10—C9	−179.68 (19)	C3—C2—O5—C1	172.2 (2)
C3—C2—C10—C9	0.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O4i	0.84	1.85	2.685 (3)	174
O4—H4A···O3	0.84	2.06	2.875 (3)	164
C7—H7···O5ii	0.95	2.56	3.494 (2)	167
C14—H14B···O2iii	0.99	2.48	3.206 (3)	130

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O4i	0.84	1.85	2.685 (3)	174
O4—H4A⋯O3	0.84	2.06	2.875 (3)	164
C7—H7⋯O5ii	0.95	2.56	3.494 (2)	167
C14—H14B⋯O2iii	0.99	2.48	3.206 (3)	130

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