Literature DB >> 22199730

3-(4-Hy-droxy-phen-yl)-7-meth-oxy-chroman-4-one monohydrate.

Zhu-Ping Xiao¹, Zhu-Yun Peng, Qun Luo, Ying Wu, Ye-Ling Yang.

Abstract

In the title compound, C(16)H(14)O(4)·H(2)O, the dihedral angle betwen the benzene rings is 71.4 (6)°. The pyran ring is in a sofa conformation. In the crystal, O-H⋯O hydrogen bonds connect the components into a two-dimensional network parallel to (010), incorporating C(2) (2)(4) and C(2) (2)(11) chains. In addition, weak C-H⋯O, C-H⋯π and π-π stacking inter-actions [centroid-centroid distance = 3.768 (2) Å] are present.

Entities: Chemical Disease Gene

Year: 2011 PMID： 22199730 PMCID： PMC3238877 DOI： 10.1107/S1600536811046034

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For background to and the biological activity of flavonoids, see: Xiao et al. (2007 ▶, 2010 ▶, 2011 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C16H14O4·H2O M = 288.29 Monoclinic, a = 9.730 (3) Å b = 17.977 (5) Å c = 8.570 (2) Å β = 106.194 (2)° V = 1439.6 (6) Å3 Z = 4 Mo Kα radiation μ = 0.10 mm−1 T = 296 K 0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.971, T max = 0.981 11487 measured reflections 3113 independent reflections 2019 reflections with I > 2σ(I) R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.051 wR(F 2) = 0.138 S = 1.04 3113 reflections 200 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.33 e Å−3 Δρmin = −0.16 e Å−3 Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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: SHELXL97. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811046034/lh5364sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811046034/lh5364Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811046034/lh5364Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₆H₁₄O₄·H₂O	F(000) = 608
M_r = 288.29	D_x = 1.330 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2114 reflections
a = 9.730 (3) Å	θ = 2.7–26.4°
b = 17.977 (5) Å	µ = 0.10 mm⁻¹
c = 8.570 (2) Å	T = 296 K
β = 106.194 (2)°	Block, colorless
V = 1439.6 (6) Å³	0.30 × 0.20 × 0.20 mm
Z = 4

Bruker SMART APEX CCD diffractometer	3113 independent reflections
Radiation source: fine-focus sealed tube	2019 reflections with I > 2σ(I)
graphite	R_int = 0.031
φ and ω scans	θ_max = 27.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.971, T_max = 0.981	k = −22→22
11487 measured reflections	l = −10→10

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0538P)² + 0.3767P] where P = (F_o² + 2F_c²)/3
3113 reflections	(Δ/σ)_max < 0.001
200 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.16 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	U_iso*/U_eq
C1	0.2951 (2)	1.04367 (12)	0.2561 (3)	0.0630 (6)
H1A	0.3289	1.0311	0.3705	0.076*
H1B	0.3722	1.0691	0.2267	0.076*
C2	0.2612 (2)	0.97338 (12)	0.1596 (3)	0.0559 (5)
H2	0.2348	0.9874	0.0445	0.067*
C3	0.1304 (2)	0.93648 (12)	0.1916 (3)	0.0541 (5)
C4	0.03218 (19)	0.98545 (10)	0.2438 (2)	0.0454 (5)
C5	−0.0930 (2)	0.95830 (11)	0.2750 (2)	0.0515 (5)
H5	−0.1103	0.9074	0.2698	0.062*
C6	−0.1897 (2)	1.00472 (11)	0.3125 (3)	0.0529 (5)
H6	−0.2720	0.9855	0.3325	0.064*
C7	−0.1647 (2)	1.08125 (12)	0.3209 (2)	0.0506 (5)
C8	−0.0416 (2)	1.11027 (11)	0.2938 (3)	0.0540 (5)
H8	−0.0246	1.1612	0.3000	0.065*
C9	0.0559 (2)	1.06186 (11)	0.2570 (2)	0.0482 (5)
C10	0.3882 (2)	0.92093 (11)	0.1881 (3)	0.0499 (5)
C11	0.4480 (2)	0.90321 (12)	0.0668 (3)	0.0569 (5)
H11	0.4123	0.9252	−0.0347	0.068*
C12	0.5599 (2)	0.85359 (12)	0.0907 (3)	0.0568 (5)
H12	0.5982	0.8421	0.0056	0.068*
C13	0.6149 (2)	0.82111 (11)	0.2404 (3)	0.0523 (5)
C14	0.5584 (2)	0.83907 (12)	0.3660 (3)	0.0587 (6)
H14	0.5963	0.8181	0.4681	0.070*
C15	0.4451 (2)	0.88844 (12)	0.3398 (3)	0.0577 (6)
H15	0.4066	0.9000	0.4246	0.069*
C16	−0.2487 (3)	1.20180 (15)	0.3705 (4)	0.0983 (10)
H16A	−0.1630	1.2133	0.4545	0.147*
H16B	−0.3294	1.2240	0.3962	0.147*
H16C	−0.2411	1.2211	0.2688	0.147*
H5A	0.949 (3)	0.8105 (17)	0.083 (3)	0.093 (9)*
H5B	0.832 (4)	0.764 (2)	−0.042 (6)	0.162 (16)*
O1	0.17584 (15)	1.09344 (8)	0.2323 (2)	0.0641 (4)
O2	0.10853 (16)	0.87006 (9)	0.1665 (2)	0.0805 (6)
O3	−0.26743 (16)	1.12282 (8)	0.3586 (2)	0.0687 (5)
O4	0.72298 (18)	0.76992 (10)	0.2689 (2)	0.0773 (5)
H4	0.7609	0.7711	0.1946	0.116*
O5	0.8803 (2)	0.77481 (10)	0.0708 (3)	0.0741 (5)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0498 (12)	0.0499 (12)	0.0940 (18)	−0.0034 (10)	0.0277 (12)	−0.0004 (11)
C2	0.0477 (11)	0.0605 (13)	0.0574 (13)	0.0027 (10)	0.0113 (10)	0.0015 (10)
C3	0.0419 (11)	0.0472 (12)	0.0660 (14)	−0.0005 (9)	0.0032 (10)	−0.0042 (10)
C4	0.0413 (10)	0.0439 (11)	0.0468 (11)	−0.0009 (8)	0.0053 (9)	0.0008 (8)
C5	0.0479 (11)	0.0453 (11)	0.0573 (13)	−0.0062 (9)	0.0080 (10)	−0.0004 (9)
C6	0.0494 (11)	0.0544 (12)	0.0562 (13)	−0.0063 (9)	0.0166 (10)	0.0014 (10)
C7	0.0499 (11)	0.0540 (12)	0.0492 (12)	0.0061 (9)	0.0160 (9)	0.0016 (9)
C8	0.0583 (12)	0.0409 (11)	0.0648 (14)	0.0025 (9)	0.0206 (11)	0.0047 (9)
C9	0.0451 (11)	0.0453 (11)	0.0539 (12)	−0.0021 (9)	0.0133 (9)	0.0054 (9)
C10	0.0406 (10)	0.0476 (11)	0.0582 (13)	−0.0005 (9)	0.0083 (9)	0.0035 (10)
C11	0.0540 (12)	0.0622 (14)	0.0508 (13)	0.0036 (10)	0.0086 (10)	0.0074 (10)
C12	0.0581 (13)	0.0614 (13)	0.0520 (13)	0.0040 (10)	0.0170 (10)	0.0025 (10)
C13	0.0458 (11)	0.0469 (11)	0.0625 (14)	0.0035 (9)	0.0123 (10)	0.0042 (10)
C14	0.0630 (13)	0.0591 (13)	0.0521 (13)	0.0042 (11)	0.0128 (11)	0.0113 (10)
C15	0.0571 (12)	0.0606 (13)	0.0607 (14)	0.0006 (10)	0.0252 (11)	−0.0004 (11)
C16	0.102 (2)	0.0595 (16)	0.152 (3)	0.0176 (15)	0.067 (2)	−0.0024 (17)
O1	0.0566 (9)	0.0436 (8)	0.0990 (12)	−0.0018 (7)	0.0331 (8)	0.0061 (8)
O2	0.0518 (9)	0.0526 (10)	0.1353 (16)	−0.0072 (7)	0.0228 (10)	−0.0261 (10)
O3	0.0678 (10)	0.0585 (10)	0.0898 (12)	0.0046 (8)	0.0385 (9)	−0.0030 (8)
O4	0.0805 (11)	0.0754 (11)	0.0794 (12)	0.0351 (9)	0.0278 (9)	0.0175 (9)
O5	0.0637 (11)	0.0722 (12)	0.0863 (14)	−0.0155 (9)	0.0206 (10)	−0.0140 (10)

C1—O1	1.434 (2)	C9—O1	1.367 (2)
C1—C2	1.496 (3)	C10—C11	1.363 (3)
C1—H1A	0.9700	C10—C15	1.392 (3)
C1—H1B	0.9700	C11—C12	1.378 (3)
C2—C10	1.519 (3)	C11—H11	0.9300
C2—C3	1.527 (3)	C12—C13	1.375 (3)
C2—H2	0.9800	C12—H12	0.9300
C3—O2	1.221 (2)	C13—O4	1.367 (2)
C3—C4	1.458 (3)	C13—C14	1.376 (3)
C4—C9	1.392 (3)	C14—C15	1.384 (3)
C4—C5	1.405 (3)	C14—H14	0.9300
C5—C6	1.362 (3)	C15—H15	0.9300
C5—H5	0.9300	C16—O3	1.432 (3)
C6—C7	1.395 (3)	C16—H16A	0.9600
C6—H6	0.9300	C16—H16B	0.9600
C7—O3	1.357 (2)	C16—H16C	0.9600
C7—C8	1.384 (3)	O4—H4	0.8200
C8—C9	1.386 (3)	O5—H5A	0.91 (3)
C8—H8	0.9300	O5—H5B	0.97 (5)

O1—C1—C2	113.81 (18)	O1—C9—C4	121.74 (17)
O1—C1—H1A	108.8	C8—C9—C4	121.99 (18)
C2—C1—H1A	108.8	C11—C10—C15	118.12 (19)
O1—C1—H1B	108.8	C11—C10—C2	121.57 (19)
C2—C1—H1B	108.8	C15—C10—C2	120.30 (19)
H1A—C1—H1B	107.7	C10—C11—C12	121.7 (2)
C1—C2—C10	113.06 (17)	C10—C11—H11	119.1
C1—C2—C3	109.50 (17)	C12—C11—H11	119.1
C10—C2—C3	112.51 (17)	C13—C12—C11	120.0 (2)
C1—C2—H2	107.1	C13—C12—H12	120.0
C10—C2—H2	107.1	C11—C12—H12	120.0
C3—C2—H2	107.1	O4—C13—C12	122.2 (2)
O2—C3—C4	123.18 (19)	O4—C13—C14	118.25 (19)
O2—C3—C2	120.41 (19)	C12—C13—C14	119.57 (19)
C4—C3—C2	116.32 (18)	C13—C14—C15	119.8 (2)
C9—C4—C5	117.36 (18)	C13—C14—H14	120.1
C9—C4—C3	120.86 (17)	C15—C14—H14	120.1
C5—C4—C3	121.71 (18)	C14—C15—C10	120.8 (2)
C6—C5—C4	121.66 (19)	C14—C15—H15	119.6
C6—C5—H5	119.2	C10—C15—H15	119.6
C4—C5—H5	119.2	O3—C16—H16A	109.5
C5—C6—C7	119.60 (19)	O3—C16—H16B	109.5
C5—C6—H6	120.2	H16A—C16—H16B	109.5
C7—C6—H6	120.2	O3—C16—H16C	109.5
O3—C7—C8	124.17 (19)	H16A—C16—H16C	109.5
O3—C7—C6	115.17 (18)	H16B—C16—H16C	109.5
C8—C7—C6	120.66 (18)	C9—O1—C1	114.27 (15)
C7—C8—C9	118.69 (18)	C7—O3—C16	118.38 (18)
C7—C8—H8	120.7	C13—O4—H4	109.5
C9—C8—H8	120.7	H5A—O5—H5B	113 (3)
O1—C9—C8	116.26 (17)

O1—C1—C2—C10	−179.23 (17)	C5—C4—C9—C8	−2.2 (3)
O1—C1—C2—C3	−52.9 (2)	C3—C4—C9—C8	174.76 (19)
C1—C2—C3—O2	−158.3 (2)	C1—C2—C10—C11	−115.6 (2)
C10—C2—C3—O2	−31.6 (3)	C3—C2—C10—C11	119.7 (2)
C1—C2—C3—C4	25.1 (3)	C1—C2—C10—C15	65.6 (3)
C10—C2—C3—C4	151.69 (18)	C3—C2—C10—C15	−59.1 (3)
O2—C3—C4—C9	−174.3 (2)	C15—C10—C11—C12	1.2 (3)
C2—C3—C4—C9	2.3 (3)	C2—C10—C11—C12	−177.6 (2)
O2—C3—C4—C5	2.6 (3)	C10—C11—C12—C13	−0.6 (3)
C2—C3—C4—C5	179.13 (18)	C11—C12—C13—O4	178.0 (2)
C9—C4—C5—C6	1.7 (3)	C11—C12—C13—C14	−0.6 (3)
C3—C4—C5—C6	−175.30 (19)	O4—C13—C14—C15	−177.44 (19)
C4—C5—C6—C7	−0.1 (3)	C12—C13—C14—C15	1.3 (3)
C5—C6—C7—O3	179.76 (18)	C13—C14—C15—C10	−0.7 (3)
C5—C6—C7—C8	−0.9 (3)	C11—C10—C15—C14	−0.5 (3)
O3—C7—C8—C9	179.62 (19)	C2—C10—C15—C14	178.31 (19)
C6—C7—C8—C9	0.4 (3)	C8—C9—O1—C1	157.45 (19)
C7—C8—C9—O1	−179.64 (19)	C4—C9—O1—C1	−23.4 (3)
C7—C8—C9—C4	1.2 (3)	C2—C1—O1—C9	53.4 (3)
C5—C4—C9—O1	178.69 (18)	C8—C7—O3—C16	0.3 (3)
C3—C4—C9—O1	−4.3 (3)	C6—C7—O3—C16	179.6 (2)

Cg1 and Cg2 are the centroids of the C4–C9 and C10–C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O5	0.82	1.78	2.585 (2)	167.
O5—H5A···O2ⁱ	0.91 (3)	1.86 (3)	2.742 (3)	163 (3)
O5—H5B···O4ⁱⁱ	0.97 (5)	1.78 (5)	2.734 (3)	168 (4)
C8—H8···O5ⁱⁱⁱ	0.93	2.55	3.397 (3)	152.
C2—H2···Cg1^iv	0.98	2.86	3.745 (3)	151
C6—H6···Cg2^v	0.93	2.97	3.748 (3)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C4–C9 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O5	0.82	1.78	2.585 (2)	167
O5—H5A⋯O2ⁱ	0.91 (3)	1.86 (3)	2.742 (3)	163 (3)
O5—H5B⋯O4ⁱⁱ	0.97 (5)	1.78 (5)	2.734 (3)	168 (4)
C8—H8⋯O5ⁱⁱⁱ	0.93	2.55	3.397 (3)	152
C2—H2⋯Cg1^iv	0.98	2.86	3.745 (3)	151
C6—H6⋯Cg2^v	0.93	2.97	3.748 (3)	142

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

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