6-Bromo-3-hydr­oxy-4-oxo-2-phenyl-4H-chromene-8-carboxylic acid dimethyl­formamide disolvate

Hui-Liang Wen; Dan-Dan Chen; Chong-Bo Liu

doi:10.1107/S1600536808019454

. 2008 Jul 5;64(Pt 8):o1415. doi: 10.1107/S1600536808019454

6-Bromo-3-hydroxy-4-oxo-2-phenyl-4H-chromene-8-carboxylic acid dimethylformamide disolvate

Hui-Liang Wen ^a,^b,^*, Dan-Dan Chen ^a, Chong-Bo Liu ^c

PMCID: PMC2962049 PMID: 21203134

Abstract

In the title compound, C₁₆H₉BrO₅·2C₃H₇NO, the chromene ring system is essentially planar. The two dimethylformamide solvent molecules are linked by intermolecular O—H⋯O hydrogen bonds to the 6-bromo-3-hydroxy-4-oxo-2-phenyl-4H-chromene-8-carboxylic acid molecules.

Related literature

For related literature, see: Gills et al. (1980 ▶); Liu et al. (2007 ▶); Jin & Xiao (2005 ▶); Kagechika et al. (1989 ▶); Valenti et al. (1998 ▶); Walenta et al. (1991 ▶); Zwaagstra et al. (1996 ▶, 1998a ▶,b ▶).

Experimental

Crystal data

C₁₆H₉BrO₅·2C₃H₇NO
M _r = 507.33
Monoclinic,
a = 10.489 (2) Å
b = 11.470 (2) Å
c = 18.803 (4) Å
β = 92.127 (3)°
V = 2260.6 (8) Å³
Z = 4
Mo Kα radiation
μ = 1.86 mm⁻¹
T = 294 (2) K
0.49 × 0.38 × 0.17 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.462, T _max = 0.742
14295 measured reflections
4203 independent reflections
2889 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.036
wR(F ²) = 0.098
S = 0.99
4203 reflections
294 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson,1996 ▶); ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808019454/dn2358sup1.cif

e-64-o1415-sup1.cif^{(20.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019454/dn2358Isup2.hkl

e-64-o1415-Isup2.hkl^{(206KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O6	0.82	1.78	2.598 (2)	173
O5—H5⋯O7	0.82	1.89	2.627 (2)	149
O5—H5⋯O4	0.82	2.32	2.741 (3)	113

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Acknowledgments

This work is supported by the National Natural Science Foundation of China (20662007) and the Key Laboratory Open Foundation of Food Science of the Ministry of Education, Nanchang University (NCU200407).

supplementary crystallographic information

Comment

Flavonoids are widely present in nature, which have potential biological activity such as antiviral (Zwaagstra et al., 1996; Zwaagstra et al., 1998a), anticancer (Valenti et al., 1998), treating leukemia (Kagechika et al., 1989), antihypertensive, antimicrobial (Gills et al., 1980; Walenta et al., 1991) et al. Due to the varieties of its biological activity, the structure-activity relationships study of flavonoids carboxylic acids has been the hot spot all along. In a continuation of our recent studies of flavonoids carboxylic acids (Liu et al., 2007), we report here the title compound, C₁₆H₉BrO₅—C₆H₁₄N₂O₂, (I).

In compound (I), the chromene molecule is roughly planar, with a mean deviation of 0.0521 Å. The dihedral angle between the chromene ring and the phenyl ring is 7.5 (2)°. Two O—H···O hydrogen bonds (Table 1, Fig. 1) involving the H atoms of hydroxyl group and carboxylic acid group connect the dimethylformamide molecules and 6-bromo-3-hydroxy-4-oxo-2-phenyl-4H-chromene-8-carboxylic acid.

Experimental

The title compound was synthesized by the ring closure of 5'-bromo-3'-carboxy-2'-hydroxychalcone under the existence of a certain oxidant, according to the route published by Zwaagstra et al. (Zwaagstra et al., 1998b). Single crystals of (I) suitable for X-ray diffraction analysis were obtained from a solution in N,N-dimethylformamide.

Figures

Fig. 1. — : The molecular structure of (I), with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are represented as small spheres of arbitrary radii. The hydrogen bonds are shown as dashed lines.

Crystal data

C₁₆H₉BrO₅·2C₃H₇NO	F₀₀₀ = 1040
M_r = 507.33	D_x = 1.491 Mg m⁻³
Monoclinic, P2(1)/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3645 reflections
a = 10.489 (2) Å	θ = 2.6–23.5º
b = 11.470 (2) Å	µ = 1.86 mm⁻¹
c = 18.803 (4) Å	T = 294 (2) K
β = 92.127 (3)º	Block, yellow
V = 2260.6 (8) Å³	0.49 × 0.38 × 0.17 mm
Z = 4

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Data collection

Bruker SMART CCD diffractometer	4203 independent reflections
Radiation source: fine-focus sealed tube	2889 reflections with I > 2σ(I)
Monochromator: graphite	R_int = 0.028
T = 294(2) K	θ_max = 25.5º
φ and ω scans	θ_min = 2.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)	h = −12→11
T_min = 0.462, T_max = 0.742	k = −13→13
14295 measured reflections	l = −22→22

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Refinement

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)] = 0.036	H-atom parameters constrained
wR(F²) = 0.098	w = 1/[σ²(F_o²) + (0.0482P)² + 0.6824P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max = 0.017
4203 reflections	Δρ_max = 0.32 e Å⁻³
294 parameters	Δρ_min = −0.34 e Å⁻³
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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Special details

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 > 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.

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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

	x	y	z	U_iso*/U_eq
Br1	0.06013 (3)	0.88028 (2)	0.582768 (19)	0.07113 (15)
O1	−0.0368 (2)	0.44074 (18)	0.65009 (12)	0.0911 (8)
O2	0.06856 (17)	0.31912 (16)	0.58290 (9)	0.0577 (5)
H2A	0.0279	0.2704	0.6046	0.087*
O3	0.24560 (16)	0.40314 (13)	0.50359 (9)	0.0460 (4)
O4	0.41242 (18)	0.68075 (16)	0.41187 (10)	0.0652 (6)
O5	0.49923 (18)	0.46087 (15)	0.38343 (11)	0.0610 (5)
H5	0.5303	0.5237	0.3727	0.091*
C1	0.1082 (2)	0.5216 (2)	0.57023 (13)	0.0439 (6)
C2	0.0684 (2)	0.6327 (2)	0.58763 (14)	0.0517 (7)
H2	0.0041	0.6416	0.6199	0.062*
C3	0.1222 (2)	0.7312 (2)	0.55796 (14)	0.0495 (7)
C4	0.2183 (2)	0.7207 (2)	0.51073 (14)	0.0485 (6)
H4	0.2544	0.7869	0.4912	0.058*
C5	0.2615 (2)	0.6101 (2)	0.49221 (13)	0.0422 (6)
C6	0.2067 (2)	0.5112 (2)	0.52147 (12)	0.0411 (6)
C7	0.3634 (2)	0.5972 (2)	0.44191 (14)	0.0456 (6)
C8	0.4030 (2)	0.4787 (2)	0.42805 (13)	0.0443 (6)
C9	0.3421 (2)	0.3864 (2)	0.45729 (13)	0.0429 (6)
C10	0.0406 (3)	0.4222 (2)	0.60528 (14)	0.0518 (7)
C11	0.3633 (2)	0.2608 (2)	0.44578 (13)	0.0442 (6)
C12	0.4628 (3)	0.2186 (3)	0.40674 (19)	0.0821 (11)
H12	0.5188	0.2708	0.3865	0.099*
C13	0.4800 (4)	0.1012 (3)	0.3976 (2)	0.0944 (13)
H13	0.5482	0.0752	0.3716	0.113*
C14	0.3998 (3)	0.0217 (2)	0.42550 (17)	0.0686 (9)
H14	0.4114	−0.0578	0.4184	0.082*
C15	0.3021 (3)	0.0619 (2)	0.46419 (18)	0.0736 (9)
H15	0.2464	0.0089	0.4839	0.088*
C16	0.2840 (3)	0.1793 (2)	0.47476 (16)	0.0629 (8)
H16	0.2169	0.2041	0.5020	0.075*
N1	−0.2166 (3)	0.1136 (2)	0.71663 (13)	0.0631 (7)
O6	−0.0563 (2)	0.15290 (18)	0.64329 (11)	0.0722 (6)
C17	−0.1516 (3)	0.1828 (3)	0.67549 (16)	0.0626 (8)
H17	−0.1792	0.2595	0.6703	0.075*
C18	−0.3276 (4)	0.1567 (3)	0.7524 (2)	0.0983 (13)
H18A	−0.3072	0.1649	0.8024	0.147*
H18B	−0.3968	0.1026	0.7456	0.147*
H18C	−0.3521	0.2311	0.7329	0.147*
C19	−0.1781 (3)	−0.0070 (3)	0.72818 (18)	0.0840 (10)
H19A	−0.2251	−0.0565	0.6955	0.126*
H19B	−0.1953	−0.0294	0.7761	0.126*
H19C	−0.0885	−0.0147	0.7206	0.126*
N2	0.7254 (2)	0.78411 (18)	0.28823 (12)	0.0554 (6)
O7	0.6435 (2)	0.60874 (17)	0.31631 (12)	0.0773 (7)
C20	0.6539 (3)	0.7141 (3)	0.32545 (16)	0.0642 (8)
H20	0.6076	0.7473	0.3615	0.077*
C21	0.7365 (4)	0.9061 (3)	0.3036 (3)	0.1108 (15)
H21A	0.6909	0.9239	0.3456	0.166*
H21B	0.7012	0.9503	0.2642	0.166*
H21C	0.8248	0.9260	0.3113	0.166*
C22	0.8037 (3)	0.7385 (3)	0.23293 (16)	0.0746 (9)
H22A	0.8853	0.7160	0.2532	0.112*
H22B	0.8151	0.7974	0.1975	0.112*
H22C	0.7626	0.6718	0.2114	0.112*

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Atomic displacement parameters (Å²)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0723 (2)	0.04462 (18)	0.0983 (3)	0.00670 (14)	0.02689 (18)	−0.00929 (15)
O1	0.1120 (19)	0.0564 (13)	0.1106 (18)	−0.0065 (12)	0.0794 (16)	−0.0021 (12)
O2	0.0641 (13)	0.0440 (11)	0.0672 (12)	−0.0095 (9)	0.0321 (10)	0.0013 (9)
O3	0.0491 (10)	0.0358 (9)	0.0546 (10)	−0.0028 (7)	0.0219 (8)	0.0004 (7)
O4	0.0696 (14)	0.0428 (11)	0.0860 (14)	−0.0029 (9)	0.0389 (11)	0.0106 (10)
O5	0.0621 (13)	0.0421 (10)	0.0814 (13)	−0.0017 (9)	0.0392 (10)	0.0058 (9)
C1	0.0440 (15)	0.0429 (14)	0.0454 (14)	−0.0045 (11)	0.0098 (12)	0.0000 (11)
C2	0.0483 (16)	0.0522 (16)	0.0557 (16)	−0.0010 (12)	0.0179 (13)	−0.0043 (12)
C3	0.0501 (16)	0.0402 (14)	0.0587 (17)	0.0007 (12)	0.0073 (13)	−0.0050 (12)
C4	0.0486 (16)	0.0375 (13)	0.0600 (17)	−0.0043 (11)	0.0085 (13)	0.0032 (12)
C5	0.0411 (14)	0.0389 (13)	0.0472 (14)	−0.0012 (11)	0.0078 (11)	0.0025 (11)
C6	0.0411 (14)	0.0372 (13)	0.0455 (14)	−0.0011 (11)	0.0080 (11)	−0.0015 (11)
C7	0.0425 (15)	0.0412 (14)	0.0540 (15)	−0.0033 (11)	0.0125 (12)	0.0060 (11)
C8	0.0413 (15)	0.0429 (14)	0.0494 (14)	−0.0025 (11)	0.0131 (12)	0.0040 (11)
C9	0.0401 (14)	0.0432 (13)	0.0460 (14)	−0.0022 (11)	0.0116 (11)	0.0022 (11)
C10	0.0528 (17)	0.0501 (15)	0.0537 (16)	−0.0041 (13)	0.0197 (14)	−0.0009 (12)
C11	0.0448 (15)	0.0383 (13)	0.0500 (15)	−0.0009 (11)	0.0102 (12)	−0.0001 (11)
C12	0.083 (2)	0.0446 (16)	0.123 (3)	−0.0012 (15)	0.061 (2)	0.0002 (17)
C13	0.099 (3)	0.0519 (19)	0.137 (3)	0.0085 (18)	0.070 (3)	−0.0067 (19)
C14	0.079 (2)	0.0396 (16)	0.089 (2)	0.0024 (15)	0.0210 (18)	−0.0071 (15)
C15	0.085 (2)	0.0397 (15)	0.099 (2)	−0.0087 (16)	0.0338 (19)	0.0043 (16)
C16	0.069 (2)	0.0440 (15)	0.078 (2)	−0.0023 (14)	0.0344 (16)	−0.0023 (14)
N1	0.0694 (17)	0.0582 (15)	0.0630 (15)	−0.0122 (12)	0.0213 (13)	0.0075 (11)
O6	0.0710 (15)	0.0588 (12)	0.0889 (15)	−0.0066 (10)	0.0320 (12)	0.0131 (11)
C17	0.064 (2)	0.0532 (17)	0.072 (2)	−0.0080 (15)	0.0209 (16)	0.0106 (15)
C18	0.096 (3)	0.088 (3)	0.114 (3)	−0.014 (2)	0.057 (2)	0.004 (2)
C19	0.104 (3)	0.064 (2)	0.084 (2)	−0.0043 (19)	0.016 (2)	0.0247 (18)
N2	0.0544 (14)	0.0404 (12)	0.0727 (15)	−0.0045 (10)	0.0200 (12)	0.0015 (11)
O7	0.0906 (17)	0.0485 (13)	0.0959 (16)	−0.0178 (10)	0.0453 (13)	−0.0037 (10)
C20	0.065 (2)	0.0550 (18)	0.075 (2)	−0.0054 (15)	0.0276 (16)	−0.0033 (15)
C21	0.114 (3)	0.0420 (18)	0.180 (4)	−0.0070 (19)	0.056 (3)	−0.007 (2)
C22	0.087 (2)	0.072 (2)	0.067 (2)	−0.0156 (17)	0.0320 (18)	−0.0041 (16)

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Geometric parameters (Å, °)

Br1—C3	1.894 (2)	C14—C15	1.359 (4)
O1—C10	1.210 (3)	C14—H14	0.9300
O2—C10	1.293 (3)	C15—C16	1.376 (4)
O2—H2A	0.8200	C15—H15	0.9300
O3—C6	1.351 (3)	C16—H16	0.9300
O3—C9	1.372 (3)	N1—C17	1.316 (3)
O4—C7	1.235 (3)	N1—C18	1.453 (4)
O5—C8	1.352 (3)	N1—C19	1.455 (4)
O5—H5	0.8200	O6—C17	1.236 (3)
C1—C2	1.384 (3)	C17—H17	0.9300
C1—C6	1.412 (3)	C18—H18A	0.9600
C1—C10	1.507 (3)	C18—H18B	0.9600
C2—C3	1.389 (4)	C18—H18C	0.9600
C2—H2	0.9300	C19—H19A	0.9600
C3—C4	1.373 (3)	C19—H19B	0.9600
C4—C5	1.396 (3)	C19—H19C	0.9600
C4—H4	0.9300	N2—C20	1.318 (3)
C5—C6	1.394 (3)	N2—C21	1.433 (4)
C5—C7	1.460 (3)	N2—C22	1.447 (3)
C7—C8	1.447 (3)	O7—C20	1.225 (3)
C8—C9	1.363 (3)	C20—H20	0.9300
C9—C11	1.475 (3)	C21—H21A	0.9600
C11—C16	1.377 (3)	C21—H21B	0.9600
C11—C12	1.386 (4)	C21—H21C	0.9600
C12—C13	1.371 (4)	C22—H22A	0.9600
C12—H12	0.9300	C22—H22B	0.9600
C13—C14	1.359 (4)	C22—H22C	0.9600
C13—H13	0.9300

C10—O2—H2A	109.5	C13—C14—H14	121.0
C6—O3—C9	121.48 (18)	C14—C15—C16	121.4 (3)
C8—O5—H5	109.5	C14—C15—H15	119.3
C2—C1—C6	117.8 (2)	C16—C15—H15	119.3
C2—C1—C10	116.2 (2)	C15—C16—C11	121.2 (3)
C6—C1—C10	126.0 (2)	C15—C16—H16	119.4
C1—C2—C3	121.6 (2)	C11—C16—H16	119.4
C1—C2—H2	119.2	C17—N1—C18	120.6 (3)
C3—C2—H2	119.2	C17—N1—C19	120.9 (3)
C4—C3—C2	120.5 (2)	C18—N1—C19	118.5 (3)
C4—C3—Br1	120.38 (19)	O6—C17—N1	124.5 (3)
C2—C3—Br1	119.14 (19)	O6—C17—H17	117.7
C3—C4—C5	119.6 (2)	N1—C17—H17	117.7
C3—C4—H4	120.2	N1—C18—H18A	109.5
C5—C4—H4	120.2	N1—C18—H18B	109.5
C6—C5—C4	119.9 (2)	H18A—C18—H18B	109.5
C6—C5—C7	119.7 (2)	N1—C18—H18C	109.5
C4—C5—C7	120.4 (2)	H18A—C18—H18C	109.5
O3—C6—C5	121.0 (2)	H18B—C18—H18C	109.5
O3—C6—C1	118.3 (2)	N1—C19—H19A	109.5
C5—C6—C1	120.6 (2)	N1—C19—H19B	109.5
O4—C7—C8	121.3 (2)	H19A—C19—H19B	109.5
O4—C7—C5	123.0 (2)	N1—C19—H19C	109.5
C8—C7—C5	115.7 (2)	H19A—C19—H19C	109.5
O5—C8—C9	120.3 (2)	H19B—C19—H19C	109.5
O5—C8—C7	118.7 (2)	C20—N2—C21	122.1 (3)
C9—C8—C7	120.9 (2)	C20—N2—C22	120.7 (2)
C8—C9—O3	121.0 (2)	C21—N2—C22	117.0 (2)
C8—C9—C11	128.6 (2)	O7—C20—N2	125.2 (3)
O3—C9—C11	110.38 (19)	O7—C20—H20	117.4
O1—C10—O2	123.6 (2)	N2—C20—H20	117.4
O1—C10—C1	120.7 (2)	N2—C21—H21A	109.5
O2—C10—C1	115.7 (2)	N2—C21—H21B	109.5
C16—C11—C12	116.8 (2)	H21A—C21—H21B	109.5
C16—C11—C9	120.6 (2)	N2—C21—H21C	109.5
C12—C11—C9	122.7 (2)	H21A—C21—H21C	109.5
C13—C12—C11	121.0 (3)	H21B—C21—H21C	109.5
C13—C12—H12	119.5	N2—C22—H22A	109.5
C11—C12—H12	119.5	N2—C22—H22B	109.5
C14—C13—C12	121.6 (3)	H22A—C22—H22B	109.5
C14—C13—H13	119.2	N2—C22—H22C	109.5
C12—C13—H13	119.2	H22A—C22—H22C	109.5
C15—C14—C13	118.0 (3)	H22B—C22—H22C	109.5
C15—C14—H14	121.0

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Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O6	0.82	1.78	2.598 (2)	173
O5—H5···O7	0.82	1.89	2.627 (2)	149
O5—H5···O4	0.82	2.32	2.741 (3)	113

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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DN2358).

References

Bruker (1998). SAINT and SMART Bruker AXS Inc., Madison, Wisconsin, USA.
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
Gills, P. M., Haemers, A. & Bollaert, W. (1980). Eur. J. Med. Chem. Chim. Ther.15, 185–190.
Jin, L.-F. & Xiao, F.-P. (2005). Acta Cryst. E61, o1198–o1199.
Kagechika, H., Kawachi, E., Hashimoto, Y. & Shudo, K. (1989). J. Med. Chem 32, 834–840. [DOI] [PubMed]
Liu, C.-B., Chen, Y.-H., Zhou, X.-Y., Ding, L. & Wen, H.-L. (2007). Acta Cryst. E63, o90–o91.
Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
Valenti, P., Bisi, A., Rampa, A., Gobbi, S., Belluti, F., Da Re, P., Cima, L. & Carrara, M. (1998). Anti Cancer Drug Des 13, 881–892. [PubMed]
Walenta, R., Muller-Peddinghaus, R., Ban, I., Wurl, M. & Preuschoff, U. (1991). US Patent 5 013 852.
Zwaagstra, M. E., Korthouwer, R. E. M., Timmerman, H. & Zhang, M.-Q. (1998a). Eur J. Med. Chem 33, 95–102.
Zwaagstra, M. E., Timmerman, H., Abdoelgafoe, R. S. & Zhang, M.-Q. (1996). Eur J. Med. Chem.31, 861–874.
Zwaagstra, M. E., Zhang, M., Timmermann, H., Tamura, M. & Wada, Y. (1998b). European Patent 8 345 10.

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808019454/dn2358sup1.cif

e-64-o1415-sup1.cif^{(20.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019454/dn2358Isup2.hkl

e-64-o1415-Isup2.hkl^{(206KB, hkl)}

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

[bb1] Bruker (1998). SAINT and SMART Bruker AXS Inc., Madison, Wisconsin, USA.

[bb2] Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.

[bb3] Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.

[bb4] Gills, P. M., Haemers, A. & Bollaert, W. (1980). Eur. J. Med. Chem. Chim. Ther.15, 185–190.

[bb5] Jin, L.-F. & Xiao, F.-P. (2005). Acta Cryst. E61, o1198–o1199.

[bb6] Kagechika, H., Kawachi, E., Hashimoto, Y. & Shudo, K. (1989). J. Med. Chem 32, 834–840. [DOI] [PubMed]

[bb7] Liu, C.-B., Chen, Y.-H., Zhou, X.-Y., Ding, L. & Wen, H.-L. (2007). Acta Cryst. E63, o90–o91.

[bb8] Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.

[bb9] Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]

[bb10] Valenti, P., Bisi, A., Rampa, A., Gobbi, S., Belluti, F., Da Re, P., Cima, L. & Carrara, M. (1998). Anti Cancer Drug Des 13, 881–892. [PubMed]

[bb11] Walenta, R., Muller-Peddinghaus, R., Ban, I., Wurl, M. & Preuschoff, U. (1991). US Patent 5 013 852.

[bb12] Zwaagstra, M. E., Korthouwer, R. E. M., Timmerman, H. & Zhang, M.-Q. (1998a). Eur J. Med. Chem 33, 95–102.

[bb13] Zwaagstra, M. E., Timmerman, H., Abdoelgafoe, R. S. & Zhang, M.-Q. (1996). Eur J. Med. Chem.31, 861–874.

[bb14] Zwaagstra, M. E., Zhang, M., Timmermann, H., Tamura, M. & Wada, Y. (1998b). European Patent 8 345 10.

PERMALINK

6-Bromo-3-hydroxy-4-oxo-2-phenyl-4H-chromene-8-carboxylic acid dimethylformamide disolvate

Hui-Liang Wen

Dan-Dan Chen

Chong-Bo Liu

Abstract

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Experimental

Crystal data

Data collection

Refinement

Supplementary Material

Table 1. Hydrogen-bond geometry (Å, °).

Acknowledgments

supplementary crystallographic information

Comment

Experimental

Refinement

Figures

Fig. 1.

Crystal data

Data collection

Refinement

Special details

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

Atomic displacement parameters (Å²)

Geometric parameters (Å, °)

Hydrogen-bond geometry (Å, °)

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PERMALINK

6-Bromo-3-hydr­oxy-4-oxo-2-phenyl-4H-chromene-8-carboxylic acid dimethyl­formamide disolvate

Hui-Liang Wen

Dan-Dan Chen

Chong-Bo Liu

Abstract

Related literature

Experimental

Crystal data

Data collection

Refinement

Supplementary Material

Table 1. Hydrogen-bond geometry (Å, °).

Acknowledgments

supplementary crystallographic information

Comment

Experimental

Refinement

Figures

Fig. 1.

Crystal data

Data collection

Refinement

Special details

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

Atomic displacement parameters (Å2)

Geometric parameters (Å, °)

Hydrogen-bond geometry (Å, °)

Footnotes

References

Associated Data

Supplementary Materials

ACTIONS

PERMALINK

RESOURCES

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6-Bromo-3-hydroxy-4-oxo-2-phenyl-4H-chromene-8-carboxylic acid dimethylformamide disolvate

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

Atomic displacement parameters (Å²)