4-Hydr-oxy-3-[(2E)-3-(3,4,5-trimethoxy-phen-yl)prop-2-eno-yl]-2H-chromen-2-one.

A new chalcone of the coumarin, C(21)H(18)O(7), containing an annulated α-pyrone ring, was obtained by condensation of the borate complex of ac-yl(hydr-oxy)coumarin with trimethoxy-benzaldehyde. The structure exhibits intra-molecular hydrogen bonding between the hydroxyl oxygen and the ketonic oxygen in the coumarin group. The bicyclic coumarin fragment and the benzene ring form a dihedral angle of 17.1 (4)°. The crystal packing involves dimers inter-connected by C-H⋯O hydrogen bonding.

Related literature

For organic non-linear optical materials (NLO) of aromatic compounds with delocalized electron systems, see: Marcy et al. (1995 ▶); Zhengdong et al. (1997 ▶). For their non-linear susceptibilities, which are larger than those of inorganic optical materials, see: Chemla & Zyss (1987 ▶) and Lakshmana Perumal et al. (2002 ▶), and for their optical properties, see: Sarojini et al. (2006 ▶). For bond-length data, see: Traven et al.(2000 ▶). For the exclusive annulation of the α-pyrone ring, see Traven et al.(2007 ▶). For charge transfer from the phenyl ring to the coumarin system, see Indira et al. (2002 ▶); Sun & Cui (2008 ▶).

Experimental

Crystal data

C21H18O7

M = 382.35

Triclinic,

a = 4.1370 (2) Å

b = 8.1247 (2) Å

c = 14.4101 (2) Å

α = 74.549 (10)°

β = 85.166 (10)°

γ = 81.205 (10)°

V = 460.87 (4) Å3

Z = 1

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.16 × 0.13 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.981, T max = 0.99

3575 measured reflections

1974 independent reflections

1200 reflections with I > 2σ(I)

R int = 0.038

2 standard reflections frequency: 120 min intensity decay: 1.1%

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.136

S = 1.09

1974 reflections

257 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.12 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CAD-4 EXPRESS (Duisenberg, 1992 ▶; Macíček & Yordanov, 1992 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809022569/hg2517sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022569/hg2517Isup2.hkl

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

C21H18O7	Z = 1
Mr = 382.35	F(000) = 200
Triclinic, P1	Dx = 1.378 Mg m−3
Hall symbol: P 1	Melting point: 466 K
a = 4.1370 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.1247 (2) Å	Cell parameters from 25 reflections
c = 14.4101 (2) Å	θ = 10–15°
α = 74.549 (10)°	µ = 0.10 mm−1
β = 85.166 (10)°	T = 293 K
γ = 81.205 (10)°	Prism, pale yellow
V = 460.87 (4) Å3	0.16 × 0.13 × 0.10 mm

Enraf–Nonius CAD-4 diffractometer	1200 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.038
graphite	θmax = 27.0°, θmin = 2.6°
ω/2θ scans	h = −5→5
Absorption correction: ψ scan (North et al., 1968)	k = −10→10
Tmin = 0.981, Tmax = 0.99	l = −18→18
3575 measured reflections	2 standard reflections every 120 min
1974 independent reflections	intensity decay: 1.1%

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0571P)2 + 0.0544P] where P = (Fo2 + 2Fc2)/3
1974 reflections	(Δ/σ)max < 0.001
257 parameters	Δρmax = 0.12 e Å−3
3 restraints	Δρmin = −0.19 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	0.2654 (9)	−0.1096 (4)	0.5125 (2)	0.0645 (9)
C8	0.4138 (11)	0.1778 (6)	0.4904 (3)	0.0540 (12)
O4	0.5686 (10)	0.4521 (5)	0.4679 (2)	0.0763 (11)
C7	0.3170 (11)	0.2208 (6)	0.3944 (3)	0.0540 (12)
C4	0.1785 (11)	0.0992 (6)	0.3577 (3)	0.0529 (12)
O3	0.3412 (9)	0.3741 (5)	0.3374 (2)	0.0727 (10)
O7	0.9754 (9)	0.6931 (4)	0.8955 (2)	0.0676 (10)
C14	0.8343 (12)	0.5498 (6)	0.7785 (3)	0.0574 (12)
H14	0.8904	0.6386	0.7268	0.069*
C15	0.8677 (11)	0.5584 (6)	0.8721 (3)	0.0550 (12)
C5	0.1553 (11)	−0.0634 (6)	0.4199 (3)	0.0563 (12)
C11	0.5772 (13)	0.2864 (7)	0.6294 (3)	0.0620 (13)
H11	0.5408	0.1837	0.6737	0.074*
C18	0.6315 (12)	0.2749 (6)	0.8389 (3)	0.0550 (12)
H18	0.5527	0.1810	0.8277	0.066*
C17	0.6645 (11)	0.2824 (6)	0.9330 (3)	0.0574 (13)
C10	0.5255 (12)	0.3065 (6)	0.5273 (3)	0.0557 (12)
O6	0.8319 (9)	0.4264 (5)	1.0432 (2)	0.0717 (10)
O2	0.5147 (10)	−0.0605 (5)	0.6284 (2)	0.0818 (12)
O5	0.5901 (9)	0.1598 (4)	1.0150 (2)	0.0676 (10)
C16	0.7836 (12)	0.4233 (7)	0.9499 (3)	0.0574 (12)
C13	0.7168 (11)	0.4083 (6)	0.7613 (3)	0.0533 (12)
C12	0.6741 (12)	0.4098 (6)	0.6607 (3)	0.0567 (12)
H12	0.7201	0.5080	0.6139	0.068*
C9	0.4048 (11)	0.0011 (6)	0.5495 (3)	0.0561 (12)
C6	0.0243 (14)	−0.1878 (8)	0.3905 (4)	0.0703 (14)
H6	0.0077	−0.2955	0.4324	0.084*
C3	0.0705 (12)	0.1366 (7)	0.2638 (3)	0.0658 (14)
H3	0.0857	0.2442	0.2216	0.079*
C2	−0.0584 (14)	0.0129 (8)	0.2341 (4)	0.0771 (17)
H2	−0.1300	0.0374	0.1718	0.093*
C19	1.0800 (14)	0.8268 (7)	0.8172 (4)	0.0708 (14)
H19A	1.1521	0.9128	0.8421	0.106*
H19B	0.9008	0.8784	0.7762	0.106*
H19C	1.2573	0.7788	0.7808	0.106*
C21	0.4581 (15)	0.0164 (7)	1.0030 (4)	0.0723 (15)
H21A	0.4186	−0.0602	1.0649	0.108*
H21B	0.6104	−0.0433	0.9650	0.108*
H21C	0.2559	0.0555	0.9708	0.108*
C1	−0.0816 (14)	−0.1476 (9)	0.2969 (4)	0.0784 (16)
H1	−0.1693	−0.2298	0.2762	0.094*
C20	0.5788 (16)	0.5207 (8)	1.0864 (4)	0.0821 (16)
H20A	0.6344	0.5155	1.1506	0.123*
H20B	0.3794	0.4724	1.0890	0.123*
H20C	0.5495	0.6385	1.0492	0.123*
H4	0.478 (14)	0.441 (7)	0.387 (4)	0.086 (17)*

	U11	U22	U33	U12	U13	U23
O1	0.080 (2)	0.064 (2)	0.0421 (17)	−0.0060 (18)	−0.0092 (15)	−0.0010 (15)
C8	0.057 (3)	0.063 (3)	0.036 (2)	0.003 (2)	−0.0032 (19)	−0.009 (2)
O4	0.113 (3)	0.070 (2)	0.0431 (19)	−0.015 (2)	−0.0111 (19)	−0.0063 (17)
C7	0.058 (3)	0.063 (3)	0.033 (2)	0.001 (2)	0.005 (2)	−0.005 (2)
C4	0.054 (3)	0.062 (3)	0.037 (2)	0.004 (2)	−0.006 (2)	−0.010 (2)
O3	0.107 (3)	0.069 (2)	0.0371 (17)	−0.009 (2)	−0.0028 (17)	−0.0052 (16)
O7	0.081 (3)	0.067 (2)	0.055 (2)	−0.0096 (18)	−0.0085 (17)	−0.0155 (17)
C14	0.062 (3)	0.055 (3)	0.047 (2)	0.005 (2)	−0.004 (2)	−0.006 (2)
C15	0.052 (3)	0.065 (3)	0.047 (3)	0.007 (2)	−0.013 (2)	−0.020 (2)
C5	0.053 (3)	0.069 (3)	0.042 (2)	0.002 (2)	0.001 (2)	−0.013 (2)
C11	0.073 (3)	0.068 (3)	0.039 (2)	0.003 (3)	−0.006 (2)	−0.008 (2)
C18	0.066 (3)	0.051 (3)	0.044 (2)	0.001 (2)	−0.011 (2)	−0.009 (2)
C17	0.064 (3)	0.062 (3)	0.046 (2)	0.006 (2)	−0.007 (2)	−0.019 (2)
C10	0.065 (3)	0.065 (3)	0.031 (2)	0.002 (2)	−0.0040 (19)	−0.007 (2)
O6	0.084 (2)	0.086 (2)	0.0477 (18)	0.0038 (19)	−0.0186 (17)	−0.0248 (18)
O2	0.119 (3)	0.074 (2)	0.0463 (19)	−0.012 (2)	−0.031 (2)	0.0023 (16)
O5	0.093 (3)	0.069 (2)	0.0383 (16)	−0.0153 (19)	−0.0088 (16)	−0.0046 (15)
C16	0.063 (3)	0.065 (3)	0.040 (2)	0.005 (2)	−0.013 (2)	−0.012 (2)
C13	0.059 (3)	0.054 (3)	0.042 (2)	0.010 (2)	−0.009 (2)	−0.012 (2)
C12	0.069 (3)	0.062 (3)	0.035 (2)	0.000 (2)	−0.009 (2)	−0.008 (2)
C9	0.060 (3)	0.062 (3)	0.043 (3)	−0.007 (2)	−0.006 (2)	−0.008 (2)
C6	0.072 (3)	0.077 (3)	0.062 (3)	−0.014 (3)	0.008 (3)	−0.018 (3)
C3	0.066 (3)	0.090 (4)	0.040 (2)	−0.003 (3)	−0.008 (2)	−0.016 (2)
C2	0.071 (4)	0.107 (5)	0.048 (3)	0.001 (3)	−0.011 (3)	−0.016 (3)
C19	0.073 (4)	0.073 (3)	0.062 (3)	−0.006 (3)	−0.014 (3)	−0.010 (3)
C21	0.094 (4)	0.073 (3)	0.051 (3)	−0.022 (3)	0.002 (3)	−0.013 (3)
C1	0.071 (4)	0.102 (5)	0.072 (4)	−0.013 (3)	−0.006 (3)	−0.039 (3)
C20	0.097 (4)	0.095 (4)	0.054 (3)	−0.003 (3)	0.000 (3)	−0.026 (3)

O1—C9	1.375 (6)	C17—O5	1.375 (6)
O1—C5	1.384 (5)	C17—C16	1.397 (6)
C8—C7	1.410 (6)	O6—C16	1.383 (5)
C8—C10	1.440 (7)	O6—C20	1.403 (6)
C8—C9	1.466 (6)	O2—C9	1.210 (5)
O4—C10	1.290 (6)	O5—C21	1.415 (6)
O4—H4	1.28 (7)	C13—C12	1.471 (6)
C7—O3	1.310 (5)	C12—H12	0.9300
C7—C4	1.445 (6)	C6—C1	1.392 (8)
C4—C5	1.396 (6)	C6—H6	0.9300
C4—C3	1.402 (6)	C3—C2	1.381 (8)
O3—H4	1.22 (7)	C3—H3	0.9300
O7—C15	1.372 (6)	C2—C1	1.387 (9)
O7—C19	1.431 (6)	C2—H2	0.9300
C14—C15	1.389 (6)	C19—H19A	0.9600
C14—C13	1.401 (7)	C19—H19B	0.9600
C14—H14	0.9300	C19—H19C	0.9600
C15—C16	1.406 (6)	C21—H21A	0.9600
C5—C6	1.388 (7)	C21—H21B	0.9600
C11—C12	1.329 (7)	C21—H21C	0.9600
C11—C10	1.467 (6)	C1—H1	0.9300
C11—H11	0.9300	C20—H20A	0.9600
C18—C17	1.392 (6)	C20—H20B	0.9600
C18—C13	1.398 (6)	C20—H20C	0.9600
C18—H18	0.9300
C9—O1—C5	122.3 (4)	C18—C13—C14	119.8 (4)
C7—C8—C10	119.6 (4)	C18—C13—C12	122.2 (4)
C7—C8—C9	118.8 (4)	C14—C13—C12	118.0 (4)
C10—C8—C9	121.7 (4)	C11—C12—C13	127.2 (4)
C10—O4—H4	104 (3)	C11—C12—H12	116.4
O3—C7—C8	120.7 (4)	C13—C12—H12	116.4
O3—C7—C4	118.4 (4)	O2—C9—O1	115.4 (4)
C8—C7—C4	120.9 (4)	O2—C9—C8	126.4 (5)
C5—C4—C3	119.3 (4)	O1—C9—C8	118.2 (4)
C5—C4—C7	117.4 (4)	C5—C6—C1	118.5 (5)
C3—C4—C7	123.3 (4)	C5—C6—H6	120.8
C7—O3—H4	102 (3)	C1—C6—H6	120.8
C15—O7—C19	116.8 (4)	C2—C3—C4	119.7 (5)
C15—C14—C13	120.5 (4)	C2—C3—H3	120.1
C15—C14—H14	119.8	C4—C3—H3	120.1
C13—C14—H14	119.8	C3—C2—C1	120.3 (5)
O7—C15—C14	124.4 (4)	C3—C2—H2	119.9
O7—C15—C16	116.2 (4)	C1—C2—H2	119.9
C14—C15—C16	119.4 (4)	O7—C19—H19A	109.5
O1—C5—C6	116.8 (4)	O7—C19—H19B	109.5
O1—C5—C4	122.1 (4)	H19A—C19—H19B	109.5
C6—C5—C4	121.1 (4)	O7—C19—H19C	109.5
C12—C11—C10	122.3 (5)	H19A—C19—H19C	109.5
C12—C11—H11	118.9	H19B—C19—H19C	109.5
C10—C11—H11	118.9	O5—C21—H21A	109.5
C17—C18—C13	120.1 (4)	O5—C21—H21B	109.5
C17—C18—H18	120.0	H21A—C21—H21B	109.5
C13—C18—H18	120.0	O5—C21—H21C	109.5
O5—C17—C18	125.6 (4)	H21A—C21—H21C	109.5
O5—C17—C16	114.5 (4)	H21B—C21—H21C	109.5
C18—C17—C16	120.0 (4)	C2—C1—C6	121.0 (5)
O4—C10—C8	118.3 (4)	C2—C1—H1	119.5
O4—C10—C11	117.4 (5)	C6—C1—H1	119.5
C8—C10—C11	124.2 (4)	O6—C20—H20A	109.5
C16—O6—C20	115.6 (4)	O6—C20—H20B	109.5
C17—O5—C21	117.3 (4)	H20A—C20—H20B	109.5
O6—C16—C17	119.9 (4)	O6—C20—H20C	109.5
O6—C16—C15	119.9 (4)	H20A—C20—H20C	109.5
C17—C16—C15	120.2 (4)	H20B—C20—H20C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O3—H4···O4	1.22 (6)	1.28 (6)	2.437 (5)	153 (5)
C2—H2···O5i	0.93	2.52	3.427 (6)	167
C20—H20B···O6ii	0.96	2.52	3.439 (8)	160
C19—H19C···O2iii	0.96	2.48	3.135 (7)	125
C11—H11···O2	0.93	2.27	2.873 (7)	122
C12—H12···O4	0.93	2.42	2.772 (5)	102

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H4⋯O4	1.22 (6)	1.28 (6)	2.437 (5)	153 (5)
C2—H2⋯O5i	0.93	2.52	3.427 (6)	167
C20—H20B⋯O6ii	0.96	2.52	3.439 (8)	160
C19—H19C⋯O2iii	0.96	2.48	3.135 (7)	125
C11—H11⋯O2	0.93	2.27	2.873 (7)	122
C12—H12⋯O4	0.93	2.42	2.772 (5)	102

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