(Z)-3-(1-Hy-droxy-3-oxobut-1-en-yl)-6-nitro-2H-chromen-2-one.

In the title compound, C(13)H(9)NO(6), the coumarin system has the benzene ring aligned at 0.61 (18)° with respect to the pyrone ring. An intra-molecular O-H⋯O hydrogen bond stabilizes the mol-ecular conformation and a C-H⋯O contact also occurs. In the crystal, weak C-H⋯O inter-actions link the mol-ecules, forming inversion dimers.

Related literature

For the biological importance of flavinoids and coumarins, see: Murry et al. (1982 ▶); Andersen et al. (2006 ▶); Murakami et al. (2001 ▶); Wu et al. (2003 ▶). For their use as fluorescent probes and triplet sensitisers, see: Wagner (2009 ▶); Takadate et al. (1995 ▶). For a related structure, see: Da & Quan (2010 ▶).

Experimental

Crystal data

C13H9NO6

M = 275.21

Triclinic,

a = 7.4591 (13) Å

b = 8.2178 (19) Å

c = 10.0087 (18) Å

α = 85.202 (17)°

β = 77.346 (15)°

γ = 89.278 (17)°

V = 596.5 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.12 mm−1

T = 293 K

0.4 × 0.32 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.917, T max = 1.000

4789 measured reflections

2093 independent reflections

1395 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.170

S = 0.93

2093 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.20 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812051872/sj5289sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812051872/sj5289Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812051872/sj5289Isup3.cml

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

C13H9NO6	Z = 2
Mr = 275.21	F(000) = 284
Triclinic, P1	Dx = 1.532 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4591 (13) Å	Cell parameters from 2257 reflections
b = 8.2178 (19) Å	θ = 3.1–29.1°
c = 10.0087 (18) Å	µ = 0.12 mm−1
α = 85.202 (17)°	T = 293 K
β = 77.346 (15)°	Plate, colorless
γ = 89.278 (17)°	0.4 × 0.32 × 0.2 mm
V = 596.5 (2) Å3

Oxford Diffraction Xcalibur Eos diffractometer	2093 independent reflections
Radiation source: fine-focus sealed tube	1395 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
Detector resolution: 15.9821 pixels mm-1	θmax = 25.0°, θmin = 3.1°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −9→8
Tmin = 0.917, Tmax = 1.000	l = −11→11
4789 measured reflections

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.170	H-atom parameters constrained
S = 0.93	w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3
2093 reflections	(Δ/σ)max < 0.001
183 parameters	Δρmax = 0.18 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	0.25449 (19)	0.17075 (18)	0.16604 (16)	0.0422 (5)
C4	0.5804 (3)	0.1391 (2)	0.1024 (2)	0.0306 (5)
C2	0.4261 (3)	0.3162 (2)	−0.0432 (2)	0.0318 (5)
C5	0.7376 (3)	0.0665 (2)	0.1335 (2)	0.0350 (6)
H5	0.8525	0.0887	0.0766	0.042*
C3	0.5812 (3)	0.2510 (2)	−0.0161 (2)	0.0329 (5)
H3	0.6927	0.2791	−0.0757	0.040*
C9	0.4119 (3)	0.1020 (3)	0.1911 (2)	0.0337 (5)
O3	0.6017 (2)	0.4703 (2)	−0.23192 (17)	0.0497 (5)
H3A	0.5984	0.5364	−0.2974	0.075*
O4	0.4619 (3)	0.6406 (2)	−0.40237 (18)	0.0584 (6)
C11	0.2837 (3)	0.4849 (3)	−0.2152 (2)	0.0417 (6)
H11	0.1660	0.4551	−0.1668	0.050*
C6	0.7191 (3)	−0.0382 (3)	0.2494 (2)	0.0367 (6)
C8	0.3959 (3)	−0.0051 (3)	0.3076 (2)	0.0402 (6)
H8	0.2815	−0.0284	0.3648	0.048*
O2	0.1007 (2)	0.3272 (2)	0.04475 (19)	0.0620 (6)
C10	0.4319 (3)	0.4287 (2)	−0.1671 (2)	0.0344 (6)
N1	0.8848 (3)	−0.1149 (2)	0.2826 (2)	0.0474 (6)
C7	0.5514 (3)	−0.0762 (3)	0.3373 (2)	0.0393 (6)
H7	0.5444	−0.1485	0.4149	0.047*
C1	0.2494 (3)	0.2775 (3)	0.0523 (2)	0.0394 (6)
O6	0.8773 (3)	−0.1692 (3)	0.3998 (2)	0.0900 (8)
O5	1.0203 (2)	−0.1232 (2)	0.1907 (2)	0.0639 (6)
C13	0.1405 (4)	0.6402 (4)	−0.3939 (3)	0.0728 (9)
H13A	0.1784	0.6891	−0.4863	0.109*
H13B	0.0716	0.7180	−0.3369	0.109*
H13C	0.0651	0.5462	−0.3932	0.109*
C12	0.3071 (4)	0.5893 (3)	−0.3397 (3)	0.0474 (6)

	U11	U22	U33	U12	U13	U23
O1	0.0340 (9)	0.0494 (10)	0.0382 (10)	0.0047 (7)	−0.0036 (7)	0.0134 (7)
C4	0.0345 (12)	0.0279 (12)	0.0291 (12)	−0.0022 (8)	−0.0071 (9)	0.0012 (8)
C2	0.0367 (12)	0.0279 (12)	0.0297 (13)	−0.0012 (9)	−0.0064 (10)	0.0017 (9)
C5	0.0315 (12)	0.0373 (13)	0.0348 (13)	−0.0012 (9)	−0.0054 (10)	0.0014 (10)
C3	0.0332 (12)	0.0324 (12)	0.0302 (12)	−0.0031 (9)	−0.0022 (9)	0.0024 (9)
C9	0.0344 (12)	0.0354 (12)	0.0308 (12)	0.0018 (9)	−0.0076 (9)	0.0013 (9)
O3	0.0494 (11)	0.0562 (12)	0.0381 (11)	−0.0036 (8)	−0.0053 (8)	0.0177 (8)
O4	0.0770 (13)	0.0554 (12)	0.0395 (11)	−0.0030 (9)	−0.0123 (9)	0.0143 (8)
C11	0.0491 (15)	0.0397 (14)	0.0365 (14)	0.0011 (10)	−0.0135 (11)	0.0062 (10)
C6	0.0406 (13)	0.0361 (13)	0.0363 (13)	0.0046 (9)	−0.0156 (10)	−0.0016 (9)
C8	0.0383 (13)	0.0486 (14)	0.0295 (13)	−0.0025 (10)	−0.0022 (10)	0.0068 (10)
O2	0.0348 (10)	0.0816 (14)	0.0625 (13)	0.0106 (8)	−0.0080 (8)	0.0261 (10)
C10	0.0436 (13)	0.0297 (12)	0.0287 (12)	−0.0019 (9)	−0.0059 (10)	0.0003 (9)
N1	0.0478 (13)	0.0527 (13)	0.0445 (13)	0.0056 (9)	−0.0198 (10)	0.0041 (10)
C7	0.0482 (14)	0.0403 (13)	0.0283 (13)	0.0022 (10)	−0.0089 (10)	0.0049 (9)
C1	0.0409 (13)	0.0405 (14)	0.0342 (13)	0.0030 (10)	−0.0066 (10)	0.0065 (10)
O6	0.0764 (15)	0.142 (2)	0.0506 (13)	0.0326 (14)	−0.0257 (11)	0.0264 (13)
O5	0.0431 (11)	0.0806 (14)	0.0632 (14)	0.0153 (9)	−0.0091 (9)	0.0125 (10)
C13	0.090 (2)	0.078 (2)	0.0564 (19)	0.0096 (16)	−0.0389 (17)	0.0148 (15)
C12	0.0694 (18)	0.0401 (14)	0.0362 (14)	0.0019 (12)	−0.0209 (13)	0.0022 (11)

O1—C9	1.360 (3)	C11—C12	1.432 (3)
O1—C1	1.385 (3)	C11—H11	0.9300
C4—C9	1.391 (3)	C6—C7	1.384 (3)
C4—C5	1.392 (3)	C6—N1	1.470 (3)
C4—C3	1.438 (3)	C8—C7	1.370 (3)
C2—C3	1.341 (3)	C8—H8	0.9300
C2—C1	1.470 (3)	O2—O2	0.0000
C2—C10	1.476 (3)	O2—C1	1.192 (3)
C5—C6	1.368 (3)	N1—O6	1.210 (3)
C5—H5	0.9300	N1—O5	1.214 (2)
C3—H3	0.9300	C7—H7	0.9300
C9—C8	1.385 (3)	C1—O2	1.192 (3)
O3—C10	1.325 (3)	C13—C12	1.502 (4)
O3—H3A	0.8200	C13—H13A	0.9600
O4—O4	0.000 (5)	C13—H13B	0.9600
O4—C12	1.247 (3)	C13—H13C	0.9600
C11—C10	1.361 (3)	C12—O4	1.247 (3)
C9—O1—C1	123.35 (17)	O3—C10—C11	121.5 (2)
C9—C4—C5	118.4 (2)	O3—C10—C2	112.69 (18)
C9—C4—C3	117.68 (19)	C11—C10—C2	125.8 (2)
C5—C4—C3	123.93 (19)	O6—N1—O5	123.5 (2)
C3—C2—C1	119.73 (19)	O6—N1—C6	118.0 (2)
C3—C2—C10	120.49 (19)	O5—N1—C6	118.4 (2)
C1—C2—C10	119.77 (18)	C8—C7—C6	118.7 (2)
C6—C5—C4	118.5 (2)	C8—C7—H7	120.7
C6—C5—H5	120.8	C6—C7—H7	120.7
C4—C5—H5	120.8	O2—C1—O2	0.00 (18)
C2—C3—C4	121.97 (19)	O2—C1—O1	115.3 (2)
C2—C3—H3	119.0	O2—C1—O1	115.3 (2)
C4—C3—H3	119.0	O2—C1—C2	128.1 (2)
O1—C9—C8	117.09 (19)	O2—C1—C2	128.1 (2)
O1—C9—C4	120.68 (19)	O1—C1—C2	116.55 (18)
C8—C9—C4	122.2 (2)	C12—C13—H13A	109.5
C10—O3—H3A	109.5	C12—C13—H13B	109.5
O4—O4—C12	0 (10)	H13A—C13—H13B	109.5
C10—C11—C12	120.7 (2)	C12—C13—H13C	109.5
C10—C11—H11	119.7	H13A—C13—H13C	109.5
C12—C11—H11	119.7	H13B—C13—H13C	109.5
C5—C6—C7	123.2 (2)	O4—C12—O4	0.0 (2)
C5—C6—N1	118.6 (2)	O4—C12—C11	121.4 (2)
C7—C6—N1	118.2 (2)	O4—C12—C11	121.4 (2)
C7—C8—C9	119.0 (2)	O4—C12—C13	119.6 (2)
C7—C8—H8	120.5	O4—C12—C13	119.6 (2)
C9—C8—H8	120.5	C11—C12—C13	119.0 (3)
O2—O2—C1	0 (10)
C9—C4—C5—C6	0.2 (3)	C7—C6—N1—O6	−20.2 (4)
C3—C4—C5—C6	180.0 (2)	C5—C6—N1—O5	−21.4 (3)
C1—C2—C3—C4	2.1 (3)	C7—C6—N1—O5	158.3 (2)
C10—C2—C3—C4	−179.02 (19)	C9—C8—C7—C6	0.0 (4)
C9—C4—C3—C2	−1.2 (3)	C5—C6—C7—C8	−0.4 (4)
C5—C4—C3—C2	178.94 (19)	N1—C6—C7—C8	179.8 (2)
C1—O1—C9—C8	−178.8 (2)	O2—O2—C1—O1	0.00 (3)
C1—O1—C9—C4	1.2 (3)	O2—O2—C1—C2	0.00 (10)
C5—C4—C9—O1	179.40 (19)	C9—O1—C1—O2	179.87 (19)
C3—C4—C9—O1	−0.4 (3)	C9—O1—C1—O2	179.87 (19)
C5—C4—C9—C8	−0.6 (3)	C9—O1—C1—C2	−0.4 (3)
C3—C4—C9—C8	179.6 (2)	C3—C2—C1—O2	178.4 (2)
C4—C5—C6—C7	0.3 (4)	C10—C2—C1—O2	−0.5 (4)
C4—C5—C6—N1	−179.93 (18)	C3—C2—C1—O2	178.4 (2)
O1—C9—C8—C7	−179.48 (18)	C10—C2—C1—O2	−0.5 (4)
C4—C9—C8—C7	0.5 (4)	C3—C2—C1—O1	−1.2 (3)
C12—C11—C10—O3	1.0 (4)	C10—C2—C1—O1	179.84 (19)
C12—C11—C10—C2	−177.7 (2)	O4—O4—C12—C11	0.00 (14)
C3—C2—C10—O3	−8.2 (3)	O4—O4—C12—C13	0.00 (10)
C1—C2—C10—O3	170.69 (19)	C10—C11—C12—O4	−4.9 (4)
C3—C2—C10—C11	170.6 (2)	C10—C11—C12—O4	−4.9 (4)
C1—C2—C10—C11	−10.5 (3)	C10—C11—C12—C13	176.3 (2)
C5—C6—N1—O6	160.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O4	0.82	1.78	2.510 (2)	147
C11—H11···O2	0.93	2.24	2.870 (3)	125
C3—H3···O5i	0.93	2.58	3.308 (3)	136
C7—H7···O4ii	0.93	2.39	3.304 (3)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O4	0.82	1.78	2.510 (2)	147
C11—H11⋯O2	0.93	2.24	2.870 (3)	125
C3—H3⋯O5i	0.93	2.58	3.308 (3)	136
C7—H7⋯O4ii	0.93	2.39	3.304 (3)	166

Symmetry codes: (i) ; (ii) .