11-(3-Chloro-2-hydroxy­prop­oxy)-2,3,9-trimethoxy­chromeno[3,4-b]chromen-12(6H)-one

Sangthong, S.; Teerawatananond, T.; Phurut, C.; Ngamrojanavanich, N.; Muangsin, N.

doi:10.1107/S1600536809018595

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1372

doi:10.1107/S1600536809018595

Open

access

11-(3-Chloro-2-hydroxypropoxy)-2,3,9-trimethoxychromeno[3,4-b]chromen-12(6H)-one

Supranee Sangthong,^a Thapong Teerawatananond,^b Chuttree Phurut,^b Nattaya Ngamrojanavanich ^b and Nongnuj Muangsin ^b ^*

^aBiotechnology Programme, Research Centre for Bioorganic Chemistry, Faculty of Science, Chulalongkorn University, Pathumwan, Bangkok 10330, Thailand, and ^bResearch Centre for Bioorganic Chemistry, Department of Chemistry, Faculty of Science, Chulalongkorn University, Pathumwan, Bangkok 10330, Thailand
^*Correspondence e-mail: nongnuj.j@chula.ac.th

(Received 13 May 2009; accepted 16 May 2009; online 23 May 2009)

In the title compound, C₂₂H₂₁ClO₈, the rotenoid core is nearly planar (r.m.s. deviation 0.114 Å), with the largest deviations from the least-squares plane being 0.286 (3) and 0.274 (2) Å. An intermolecular O—H⋯O hydrogen bond links two molecules into a centrosymmetric dimer having an R₂²(18) ring motif.

Related literature

For a related structure, see: Roengsumran et al. (2003 ).

Experimental

Crystal data

C₂₂H₂₁ClO₈
M_r = 448.84
Triclinic, $[P \overline 1]$
a = 7.1534 (4) Å
b = 11.7904 (6) Å
c = 12.7661 (7) Å
α = 76.901 (3)°
β = 86.991 (3)°
γ = 74.455 (3)°
V = 1010.30 (9) Å³
Z = 2
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 293 K
0.30 × 0.24 × 0.20 mm

Data collection

Bruker SMART APEXII diffractometer
Absorption correction: none
14308 measured reflections
4517 independent reflections
2879 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.080
wR(F²) = 0.268
S = 1.05
4517 reflections
272 parameters
7 restraints
H-atom parameters constrained
Δρ_max = 0.82 e Å⁻³
Δρ_min = −0.91 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8′—H8′⋯O8′ⁱ	0.82	2.2	2.81 (2)	132
O8′—H8′⋯O7ⁱ	0.82	2.54	3.297 (10)	154
O8—H8⋯O3ⁱ	0.82	1.92	2.735 (6)	169
Symmetry code: (i) -x-1, -y+2, -z.

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809018595/ng2583sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809018595/ng2583Isup2.hkl

checkCIF report

Comment top

6-Deoxyclitoriacetal, extracted from the roots of Stemona Collinsae Craib, showed strong cytotoxic activity against various human carcinoma (Roengsumran et al., 2003). In order to enhance its cytotoxic activities, the title compound was synthesized and its crystal structure was reported herein.

The bond lengths and angles in the molecules (Fig. 1) are within normal ranges and are comparable to a closely related structure (Roengsumran et al., 2003). The rotenoid core is nearly flattened with the largest deviations from the least-squares plane of 0.286 (3) at C14 and -0.274 (2) at O2.

In the crystal structure, interatomic OH···O hydrogen bonds link the molecules into centrosymmetric dimers, forming R₂²(18) ring motifs, in which they may help in stabilize the crystal structure (Table 1).

Related literature top

For a related structure, see: Roengsumran et al. (2003).

Experimental top

To the reaction mixture of 3-(4,5-dimethoxy-2-oxiranylmethoxy-phenyl)-3-hydroxy-7-methoxy-2-methyl-5-oxiranylmethoxy-chroman-4-one (20 mg, 0.046 mmol) in 3 ml of aqueous ethyl acetate was added 1M HCl (3 ml). The mixture solution was stirred for 30 min at room temperature. The reaction mixture was evaporated to remove solvent under reduced pressure. The residue was washed with water. Organic layer was extracted with dichloromethane and dried over MgSO₄. Solvent was removed under reduced pressure and the crude product was purified by silica gel column chromatography with dichloromethane:ethyl acetate:dichloromethane (2:1:2, v/v) as elutent to give the title compound as yellow crystal (70% yield).

Computing details top

Data collection: SMART (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with disordered omitted. Displacement ellipsoids are drawn at 50% probability level.
	Fig. 2. Packing diagram of A hydrogen bonded dimer of the title compound. Hydrogen bonds are shown as dashed lines.

11-(3-Chloro-2-hydroxypropoxy)-2,3,9-trimethoxychromeno[3,4-b]chromen- 12(6H)-one top

Crystal data top

C₂₂H₂₁ClO₈	V = 1010.30 (9) Å³
M_r = 448.84	Z = 2
Triclinic, P1	F(000) = 468
Hall symbol: -P 1	D_x = 1.475 Mg m⁻³
a = 7.1534 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.7904 (6) Å	θ = 1.6–27.4°
c = 12.7661 (7) Å	µ = 0.24 mm⁻¹
α = 76.901 (3)°	T = 293 K
β = 86.991 (3)°	Prism, colourless
γ = 74.455 (3)°	0.30 × 0.24 × 0.20 mm

Data collection top

Bruker SMART APEXII diffractometer	R_int = 0.027
Radiation source: Mo	θ_max = 27.4°, θ_min = 1.6°
ω scans	h = −8→9
14308 measured reflections	k = −15→14
4517 independent reflections	l = −16→16
2879 reflections with I > 2σ(I)

Refinement top

Refinement on F²	7 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.080	w = 1/[σ²(F_o²) + (0.1402P)² + 1.0019P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.268	(Δ/σ)_max = 0.058
S = 1.05	Δρ_max = 0.82 e Å⁻³
4517 reflections	Δρ_min = −0.91 e Å⁻³
272 parameters

Crystal data top

C₂₂H₂₁ClO₈	γ = 74.455 (3)°
M_r = 448.84	V = 1010.30 (9) Å³
Triclinic, P1	Z = 2
a = 7.1534 (4) Å	Mo Kα radiation
b = 11.7904 (6) Å	µ = 0.24 mm⁻¹
c = 12.7661 (7) Å	T = 293 K
α = 76.901 (3)°	0.30 × 0.24 × 0.20 mm
β = 86.991 (3)°

Data collection top

Bruker SMART APEXII diffractometer	2879 reflections with I > 2σ(I)
14308 measured reflections	R_int = 0.027
4517 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.080	7 restraints
wR(F²) = 0.268	H-atom parameters constrained
S = 1.05	Δρ_max = 0.82 e Å⁻³
4517 reflections	Δρ_min = −0.91 e Å⁻³
272 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cl1	−0.0091 (2)	0.94031 (14)	0.19387 (18)	0.1035 (7)
O1	−0.8374 (4)	1.5195 (2)	0.1837 (2)	0.0440 (6)
O2	−0.9242 (4)	1.7345 (2)	−0.0626 (2)	0.0530 (7)
O3	−0.6183 (5)	1.2837 (2)	−0.0085 (2)	0.0565 (8)
O4	−0.5594 (5)	1.5045 (3)	−0.3767 (2)	0.0589 (8)
O5	−0.7253 (5)	1.7328 (3)	−0.4252 (2)	0.0598 (8)
O6	−0.7703 (5)	1.2142 (3)	0.5002 (2)	0.0646 (9)
O7	−0.5510 (5)	1.1103 (2)	0.1704 (2)	0.0566 (8)
C21	−0.3641 (7)	0.9229 (3)	0.1446 (4)	0.063
H21	−0.4543	0.9373	0.0849	0.075*	0.710 (5)
H21'	−0.3023	0.839	0.1856	0.075*	0.290 (5)
O8	−0.2980 (6)	0.7966 (4)	0.1808 (4)	0.064*	0.710 (5)
H8	−0.3167	0.7636	0.1337	0.096*	0.710 (5)
O8'	−0.5162 (14)	0.9032 (9)	0.0844 (8)	0.062*	0.290 (5)
H8'	−0.4975	0.9235	0.0198	0.093*	0.290 (5)
C1	−0.8078 (6)	1.3721 (4)	0.3395 (3)	0.0460 (9)
H1	−0.8647	1.4325	0.376	0.055*
C2	−0.7492 (6)	1.2532 (4)	0.3927 (3)	0.0475 (9)
C3	−0.6659 (6)	1.1635 (4)	0.3367 (3)	0.0493 (9)
H3	−0.6288	1.0833	0.3737	0.059*
C4	−0.6377 (6)	1.1925 (3)	0.2272 (3)	0.0440 (9)
C5	−0.6986 (5)	1.3151 (3)	0.1675 (3)	0.0368 (8)
C6	−0.6830 (5)	1.3541 (3)	0.0510 (3)	0.0384 (8)
C7	−0.7431 (5)	1.4857 (3)	0.0087 (3)	0.0334 (7)
C8	−0.7322 (5)	1.5470 (3)	−0.1049 (3)	0.0346 (7)
C9	−0.6415 (5)	1.4904 (3)	−0.1873 (3)	0.0383 (8)
H9	−0.5796	1.4084	−0.1704	0.046*
C10	−0.6422 (6)	1.5539 (3)	−0.2928 (3)	0.0418 (8)
C11	−0.7324 (6)	1.6778 (3)	−0.3193 (3)	0.0427 (8)
C12	−0.8198 (5)	1.7351 (3)	−0.2397 (3)	0.0437 (9)
H12	−0.8786	1.8176	−0.2565	0.052*
C13	−0.8204 (5)	1.6705 (3)	−0.1351 (3)	0.0392 (8)
C14	−0.8613 (7)	1.6920 (3)	0.0448 (3)	0.0506 (10)
H14A	−0.963	1.7257	0.091	0.061*
H14B	−0.7485	1.7195	0.0543	0.061*
C15	−0.8106 (5)	1.5572 (3)	0.0779 (3)	0.0386 (8)
C16	−0.7789 (5)	1.3987 (3)	0.2294 (3)	0.0389 (8)
C17	−0.4440 (7)	1.3837 (4)	−0.3532 (3)	0.0577 (11)
H17A	−0.3951	1.3606	−0.4189	0.087*
H17B	−0.5212	1.3315	−0.3172	0.087*
H17C	−0.3373	1.3769	−0.3075	0.087*
C18	−0.8071 (8)	1.8595 (4)	−0.4555 (4)	0.0658 (13)
H18A	−0.7916	1.8867	−0.5315	0.099*
H18B	−0.7423	1.8994	−0.4172	0.099*
H18C	−0.9427	1.878	−0.4384	0.099*
C19	−0.8712 (9)	1.3025 (5)	0.5581 (4)	0.0774 (15)
H19A	−0.8778	1.2646	0.6326	0.116*
H19B	−1.0002	1.3384	0.5293	0.116*
H19C	−0.8034	1.3639	0.5512	0.116*
C20	−0.4775 (7)	0.9901 (3)	0.2280 (4)	0.0574 (11)
H20A	−0.5823	0.9553	0.2579	0.069*
H20B	−0.3926	0.9867	0.2861	0.069*
C22	−0.1968 (9)	0.9713 (4)	0.0981 (5)	0.0854 (19)
H22A	−0.2427	1.0579	0.0714	0.102*
H22B	−0.1453	0.9357	0.0377	0.102*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0831 (11)	0.0732 (10)	0.1646 (18)	−0.0261 (8)	0.0238 (10)	−0.0457 (11)
O1	0.0532 (15)	0.0392 (14)	0.0383 (14)	−0.0067 (11)	0.0102 (11)	−0.0147 (11)
O2	0.0622 (18)	0.0374 (14)	0.0484 (16)	0.0066 (12)	0.0055 (13)	−0.0121 (12)
O3	0.087 (2)	0.0332 (14)	0.0452 (16)	−0.0064 (13)	0.0152 (14)	−0.0156 (12)
O4	0.093 (2)	0.0470 (16)	0.0332 (14)	−0.0100 (15)	0.0080 (13)	−0.0128 (12)
O5	0.084 (2)	0.0487 (16)	0.0385 (15)	−0.0118 (15)	−0.0030 (14)	−0.0003 (12)
O6	0.078 (2)	0.072 (2)	0.0392 (16)	−0.0197 (16)	0.0067 (14)	−0.0040 (15)
O7	0.078 (2)	0.0320 (14)	0.0488 (16)	−0.0001 (13)	0.0084 (14)	−0.0057 (12)
C21	0.085	0.033	0.063	0	−0.011	−0.011
C1	0.050 (2)	0.053 (2)	0.040 (2)	−0.0170 (17)	0.0080 (16)	−0.0177 (17)
C2	0.048 (2)	0.057 (2)	0.040 (2)	−0.0202 (18)	0.0058 (16)	−0.0085 (18)
C3	0.048 (2)	0.045 (2)	0.051 (2)	−0.0122 (17)	0.0055 (17)	−0.0033 (18)
C4	0.046 (2)	0.0394 (19)	0.044 (2)	−0.0087 (15)	0.0068 (15)	−0.0075 (16)
C5	0.0376 (18)	0.0336 (17)	0.0400 (19)	−0.0086 (13)	0.0051 (14)	−0.0117 (14)
C6	0.0443 (19)	0.0310 (17)	0.0410 (19)	−0.0091 (14)	0.0063 (15)	−0.0124 (15)
C7	0.0331 (17)	0.0309 (16)	0.0372 (17)	−0.0072 (12)	0.0040 (13)	−0.0121 (14)
C8	0.0335 (17)	0.0331 (17)	0.0386 (18)	−0.0091 (13)	0.0018 (13)	−0.0107 (14)
C9	0.047 (2)	0.0303 (16)	0.0366 (18)	−0.0076 (14)	0.0031 (14)	−0.0095 (14)
C10	0.049 (2)	0.0412 (19)	0.0370 (19)	−0.0118 (15)	0.0010 (15)	−0.0116 (15)
C11	0.049 (2)	0.0403 (19)	0.0364 (19)	−0.0126 (16)	−0.0054 (15)	−0.0024 (15)
C12	0.046 (2)	0.0349 (18)	0.046 (2)	−0.0046 (15)	−0.0035 (16)	−0.0057 (16)
C13	0.0401 (19)	0.0341 (18)	0.0427 (19)	−0.0053 (14)	0.0017 (14)	−0.0126 (15)
C14	0.062 (3)	0.0362 (19)	0.049 (2)	−0.0019 (17)	0.0034 (18)	−0.0157 (17)
C15	0.0379 (18)	0.0354 (18)	0.0417 (19)	−0.0064 (14)	0.0038 (14)	−0.0114 (15)
C16	0.0381 (18)	0.0401 (19)	0.0404 (19)	−0.0105 (14)	0.0043 (14)	−0.0135 (15)
C17	0.079 (3)	0.051 (2)	0.044 (2)	−0.013 (2)	0.015 (2)	−0.0207 (19)
C18	0.086 (3)	0.050 (2)	0.052 (3)	−0.013 (2)	−0.007 (2)	0.006 (2)
C19	0.102 (4)	0.093 (4)	0.038 (2)	−0.025 (3)	0.011 (2)	−0.018 (2)
C20	0.065 (3)	0.039 (2)	0.061 (3)	−0.0100 (18)	0.003 (2)	−0.0015 (19)
C22	0.117 (5)	0.037 (2)	0.079 (4)	0.004 (2)	0.039 (3)	−0.007 (2)

Geometric parameters (Å, º) top

Cl1—C22	1.772 (7)	C5—C16	1.389 (5)
O1—C15	1.343 (4)	C5—C6	1.462 (5)
O1—C16	1.369 (4)	C6—C7	1.473 (5)
O2—C13	1.386 (4)	C7—C15	1.342 (5)
O2—C14	1.402 (5)	C7—C8	1.474 (5)
O3—C6	1.233 (4)	C8—C13	1.394 (5)
O4—C10	1.367 (5)	C8—C9	1.410 (5)
O4—C17	1.415 (5)	C9—C10	1.383 (5)
O5—C11	1.366 (4)	C9—H9	0.93
O5—C18	1.420 (5)	C10—C11	1.400 (5)
O6—C2	1.359 (5)	C11—C12	1.379 (6)
O6—C19	1.428 (6)	C12—C13	1.379 (5)
O7—C4	1.342 (5)	C12—H12	0.93
O7—C20	1.412 (5)	C14—C15	1.496 (5)
C21—O8	1.410 (5)	C14—H14A	0.97
C21—O8'	1.460 (7)	C14—H14B	0.97
C21—C22	1.500 (8)	C17—H17A	0.96
C21—C20	1.538 (6)	C17—H17B	0.96
C21—H21	0.98	C17—H17C	0.96
C21—H21'	1.0012	C18—H18A	0.96
O8—H21'	0.5101	C18—H18B	0.96
O8—H8	0.82	C18—H18C	0.96
O8'—H8'	0.82	C19—H19A	0.96
C1—C2	1.373 (6)	C19—H19B	0.96
C1—C16	1.386 (5)	C19—H19C	0.96
C1—H1	0.93	C20—H20A	0.97
C2—C3	1.394 (6)	C20—H20B	0.97
C3—C4	1.379 (6)	C22—H22A	0.97
C3—H3	0.93	C22—H22B	0.97
C4—C5	1.435 (5)

C15—O1—C16	119.0 (3)	O4—C10—C11	115.4 (3)
C13—O2—C14	115.8 (3)	C9—C10—C11	119.8 (3)
C10—O4—C17	118.1 (3)	O5—C11—C12	124.9 (3)
C11—O5—C18	117.9 (3)	O5—C11—C10	115.7 (3)
C2—O6—C19	117.0 (4)	C12—C11—C10	119.4 (3)
C4—O7—C20	117.3 (3)	C13—C12—C11	120.2 (3)
O8—C21—O8'	88.0 (5)	C13—C12—H12	119.9
O8—C21—C22	109.0 (4)	C11—C12—H12	119.9
O8'—C21—C22	126.5 (6)	C12—C13—O2	115.7 (3)
O8—C21—C20	115.0 (4)	C12—C13—C8	122.5 (3)
O8'—C21—C20	103.5 (5)	O2—C13—C8	121.7 (3)
C22—C21—C20	112.9 (4)	O2—C14—C15	112.2 (3)
O8—C21—H21	106.4	O2—C14—H14A	109.2
O8'—C21—H21	22.8	C15—C14—H14A	109.2
C22—C21—H21	106.4	O2—C14—H14B	109.2
C20—C21—H21	106.4	C15—C14—H14B	109.2
O8—C21—H21'	14.8	H14A—C14—H14B	107.9
O8'—C21—H21'	101.7	O1—C15—C7	125.7 (3)
C22—C21—H21'	104.5	O1—C15—C14	111.6 (3)
C20—C21—H21'	105.8	C7—C15—C14	122.7 (3)
H21—C21—H21'	121	O1—C16—C5	121.0 (3)
C21—O8—H21'	30	O1—C16—C1	113.4 (3)
C21—O8—H8	109.5	C5—C16—C1	125.6 (3)
H21'—O8—H8	138.7	O4—C17—H17A	109.5
C21—O8'—H8'	109.5	O4—C17—H17B	109.5
C2—C1—C16	117.5 (4)	H17A—C17—H17B	109.5
C2—C1—H1	121.2	O4—C17—H17C	109.5
C16—C1—H1	121.2	H17A—C17—H17C	109.5
O6—C2—C1	123.8 (4)	H17B—C17—H17C	109.5
O6—C2—C3	115.7 (4)	O5—C18—H18A	109.5
C1—C2—C3	120.6 (4)	O5—C18—H18B	109.5
C4—C3—C2	120.8 (4)	H18A—C18—H18B	109.5
C4—C3—H3	119.6	O5—C18—H18C	109.5
C2—C3—H3	119.6	H18A—C18—H18C	109.5
O7—C4—C3	123.1 (3)	H18B—C18—H18C	109.5
O7—C4—C5	116.0 (3)	O6—C19—H19A	109.5
C3—C4—C5	120.9 (3)	O6—C19—H19B	109.5
C16—C5—C4	114.6 (3)	H19A—C19—H19B	109.5
C16—C5—C6	120.4 (3)	O6—C19—H19C	109.5
C4—C5—C6	125.0 (3)	H19A—C19—H19C	109.5
O3—C6—C5	123.4 (3)	H19B—C19—H19C	109.5
O3—C6—C7	121.5 (3)	O7—C20—C21	104.9 (3)
C5—C6—C7	115.1 (3)	O7—C20—H20A	110.8
C15—C7—C8	116.3 (3)	C21—C20—H20A	110.8
C15—C7—C6	118.4 (3)	O7—C20—H20B	110.8
C8—C7—C6	125.2 (3)	C21—C20—H20B	110.8
C13—C8—C9	116.4 (3)	H20A—C20—H20B	108.8
C13—C8—C7	118.4 (3)	C21—C22—Cl1	112.2 (4)
C9—C8—C7	125.2 (3)	C21—C22—H22A	109.2
C10—C9—C8	121.7 (3)	Cl1—C22—H22A	109.2
C10—C9—H9	119.1	C21—C22—H22B	109.2
C8—C9—H9	119.1	Cl1—C22—H22B	109.2
O4—C10—C9	124.7 (3)	H22A—C22—H22B	107.9

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O8′—H8′···O8′ⁱ	0.82	2.2	2.81 (2)	132
O8′—H8′···O7ⁱ	0.82	2.54	3.297 (10)	154
O8—H8···O3ⁱ	0.82	1.92	2.735 (6)	169

Symmetry code: (i) −x−1, −y+2, −z.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₁ClO₈
M_r	448.84
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.1534 (4), 11.7904 (6), 12.7661 (7)
α, β, γ (°)	76.901 (3), 86.991 (3), 74.455 (3)
V (Å³)	1010.30 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.30 × 0.24 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	14308, 4517, 2879
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.080, 0.268, 1.05
No. of reflections	4517
No. of parameters	272
No. of restraints	7
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.82, −0.91

Computer programs: SMART (Bruker, 2005), APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O8'—H8'···O8'ⁱ	0.82	2.2	2.81 (2)	132.3
O8'—H8'···O7ⁱ	0.82	2.54	3.297 (10)	154.1
O8—H8···O3ⁱ	0.82	1.92	2.735 (6)	169.4

Symmetry code: (i) −x−1, −y+2, −z.

Acknowledgements

The authors gratefully acknowledge funding from the Thailand Research Fund (TRF) (to NM), and from the Department of Chemistry and the Research Centre for Bioorganic Chemistry of Chulalongkorn University.

References

Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Roengsumran, S., Khorphueng, P., Chaichit, N., Jaiboon-Muangsin, N. & Petsom, A. (2003). Z. Kristallogr. New Cryst. Struct. 218, 105–106. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1372

doi:10.1107/S1600536809018595

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

11-(3-Chloro-2-hy­droxy­prop­­oxy)-2,3,9-tri­meth­oxy­chromeno[3,4-b]chromen-12(6H)-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

11-(3-Chloro-2-hydroxypropoxy)-2,3,9-trimethoxychromeno[3,4-b]chromen-12(6H)-one