The biologically active title compound, 2',5-dimethoxy-6,7-(methylenedioxy)isoflavone, C18H14O6, was isolated from the aerial parts of Iresine herbstii Hook (Amaranthaceae). The 1,3-dioxolane ring, fused to the benzopyran ring system, adopts an envelope conformation. The dihedral angle between the benzopyran ring system and the 3-phenyl ring is 62.75 (6)°.
Supporting information
CCDC reference: 255901
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.002 Å
- R factor = 0.036
- wR factor = 0.095
- Data-to-parameter ratio = 11.5
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT432_ALERT_2_C Short Inter X...Y Contact C1 .. C16 .. 3.13 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2004); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).
2',5-dimethoxy-6,7-methylenedioxyisoflavone
top
Crystal data top
C18H14O6 | Dx = 1.516 Mg m−3 |
Mr = 326.29 | Melting point: 420.65 K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.262 (3) Å | Cell parameters from 2626 reflections |
b = 7.6872 (19) Å | θ = 2.6–27.5° |
c = 16.540 (4) Å | µ = 0.12 mm−1 |
β = 93.26 (2)° | T = 120 K |
V = 1429.6 (6) Å3 | Prism, light brown |
Z = 4 | 0.50 × 0.30 × 0.30 mm |
F(000) = 680 | |
Data collection top
Kuma KM-4 CCD diffractometer | 2191 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.044 |
Enhance (Oxford Diffraction) monochromator | θmax = 25.0°, θmin = 3.1° |
Detector resolution: 16.3 pixels mm-1 | h = −13→13 |
ω scans | k = −9→6 |
7787 measured reflections | l = −19→19 |
2513 independent reflections | |
Refinement top
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.095 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.05P)2 + 0.6P] where P = (Fo2 + 2Fc2)/3 |
2513 reflections | (Δ/σ)max < 0.001 |
219 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
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. |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.66163 (9) | 1.00762 (13) | 0.36588 (6) | 0.0202 (3) | |
O2 | 0.65600 (9) | 0.78406 (14) | 0.14191 (6) | 0.0221 (3) | |
O3 | 0.89872 (9) | 0.69849 (14) | 0.17282 (6) | 0.0231 (3) | |
O4 | 1.08534 (9) | 0.72136 (14) | 0.29725 (6) | 0.0245 (3) | |
O5 | 1.06676 (9) | 0.84629 (14) | 0.42315 (6) | 0.0249 (3) | |
O6 | 0.55584 (9) | 1.16211 (14) | 0.09673 (6) | 0.0235 (3) | |
C1 | 0.56641 (13) | 1.02097 (19) | 0.31240 (9) | 0.0189 (3) | |
H1 | 0.4975 | 1.0776 | 0.3300 | 0.023* | |
C2 | 0.56271 (13) | 0.95978 (18) | 0.23628 (8) | 0.0175 (3) | |
C3 | 0.66317 (13) | 0.86185 (18) | 0.20743 (8) | 0.0174 (3) | |
C4 | 0.88082 (13) | 0.78402 (18) | 0.24385 (9) | 0.0180 (3) | |
C5 | 0.97300 (13) | 0.79029 (19) | 0.30156 (9) | 0.0193 (3) | |
C6 | 0.96182 (13) | 0.86514 (19) | 0.37721 (9) | 0.0197 (3) | |
C7 | 0.85872 (13) | 0.93934 (19) | 0.39945 (9) | 0.0198 (3) | |
H7 | 0.8514 | 0.9905 | 0.4512 | 0.024* | |
C8 | 0.76422 (13) | 0.93469 (18) | 0.34047 (9) | 0.0178 (3) | |
C9 | 0.77037 (13) | 0.86105 (17) | 0.26327 (8) | 0.0171 (3) | |
C10 | 1.15192 (14) | 0.7918 (2) | 0.36634 (9) | 0.0257 (4) | |
H10A | 1.2003 | 0.8921 | 0.3501 | 0.031* | |
H10B | 1.2059 | 0.7025 | 0.3911 | 0.031* | |
C11 | 0.45166 (13) | 0.98206 (18) | 0.18352 (9) | 0.0184 (3) | |
C12 | 0.45098 (13) | 1.08098 (18) | 0.11195 (9) | 0.0191 (3) | |
C13 | 0.34742 (13) | 1.09308 (19) | 0.06171 (9) | 0.0221 (3) | |
H13 | 0.3473 | 1.1576 | 0.0127 | 0.027* | |
C14 | 0.24483 (14) | 1.0104 (2) | 0.08368 (9) | 0.0240 (3) | |
H14 | 0.1748 | 1.0173 | 0.0490 | 0.029* | |
C15 | 0.24270 (13) | 0.9181 (2) | 0.15539 (10) | 0.0240 (3) | |
H15 | 0.1713 | 0.8645 | 0.1707 | 0.029* | |
C16 | 0.34643 (13) | 0.90465 (19) | 0.20485 (9) | 0.0211 (3) | |
H16 | 0.3453 | 0.8414 | 0.2541 | 0.025* | |
C17 | 0.55261 (14) | 1.2800 (2) | 0.02926 (9) | 0.0251 (4) | |
H17A | 0.5344 | 1.2153 | −0.0210 | 0.038* | |
H17B | 0.6301 | 1.3370 | 0.0266 | 0.038* | |
H17C | 0.4911 | 1.3681 | 0.0361 | 0.038* | |
C18 | 0.91178 (14) | 0.8101 (2) | 0.10428 (9) | 0.0271 (4) | |
H18A | 0.8343 | 0.8596 | 0.0870 | 0.041* | |
H18B | 0.9425 | 0.7426 | 0.0598 | 0.041* | |
H18C | 0.9674 | 0.9042 | 0.1193 | 0.041* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0201 (5) | 0.0234 (5) | 0.0170 (5) | 0.0025 (4) | 0.0004 (4) | −0.0012 (4) |
O2 | 0.0192 (5) | 0.0280 (6) | 0.0190 (5) | −0.0012 (4) | −0.0012 (4) | −0.0039 (4) |
O3 | 0.0260 (6) | 0.0252 (6) | 0.0181 (5) | 0.0057 (5) | 0.0004 (4) | −0.0037 (4) |
O4 | 0.0176 (5) | 0.0316 (6) | 0.0241 (6) | 0.0052 (5) | −0.0018 (4) | −0.0024 (5) |
O5 | 0.0187 (5) | 0.0354 (6) | 0.0201 (6) | 0.0006 (5) | −0.0038 (4) | −0.0002 (5) |
O6 | 0.0208 (5) | 0.0260 (6) | 0.0234 (6) | −0.0020 (4) | −0.0007 (4) | 0.0080 (4) |
C1 | 0.0170 (7) | 0.0199 (7) | 0.0196 (7) | 0.0018 (6) | −0.0002 (6) | 0.0033 (6) |
C2 | 0.0175 (7) | 0.0155 (7) | 0.0194 (7) | −0.0017 (6) | 0.0001 (6) | 0.0036 (6) |
C3 | 0.0195 (7) | 0.0149 (7) | 0.0179 (7) | −0.0028 (6) | 0.0008 (6) | 0.0026 (6) |
C4 | 0.0206 (7) | 0.0158 (7) | 0.0176 (7) | −0.0005 (6) | 0.0004 (6) | 0.0012 (6) |
C5 | 0.0174 (7) | 0.0182 (7) | 0.0224 (8) | 0.0014 (6) | 0.0027 (6) | 0.0025 (6) |
C6 | 0.0180 (7) | 0.0205 (7) | 0.0200 (7) | −0.0034 (6) | −0.0045 (6) | 0.0041 (6) |
C7 | 0.0226 (8) | 0.0209 (7) | 0.0158 (7) | −0.0024 (6) | −0.0001 (6) | −0.0002 (6) |
C8 | 0.0176 (7) | 0.0156 (7) | 0.0204 (7) | −0.0002 (6) | 0.0021 (6) | 0.0025 (6) |
C9 | 0.0192 (7) | 0.0143 (7) | 0.0178 (7) | −0.0010 (6) | 0.0007 (6) | 0.0024 (5) |
C10 | 0.0195 (8) | 0.0316 (9) | 0.0257 (8) | 0.0017 (7) | −0.0022 (6) | −0.0009 (7) |
C11 | 0.0183 (7) | 0.0166 (7) | 0.0202 (7) | 0.0034 (6) | −0.0007 (6) | −0.0022 (6) |
C12 | 0.0196 (7) | 0.0170 (7) | 0.0210 (7) | 0.0020 (6) | 0.0023 (6) | −0.0020 (6) |
C13 | 0.0249 (8) | 0.0211 (8) | 0.0201 (7) | 0.0038 (6) | −0.0015 (6) | 0.0000 (6) |
C14 | 0.0203 (8) | 0.0256 (8) | 0.0255 (8) | 0.0032 (6) | −0.0050 (6) | −0.0027 (6) |
C15 | 0.0179 (7) | 0.0233 (8) | 0.0308 (8) | 0.0002 (6) | 0.0015 (6) | 0.0004 (6) |
C16 | 0.0227 (8) | 0.0190 (7) | 0.0216 (8) | 0.0026 (6) | 0.0026 (6) | 0.0021 (6) |
C17 | 0.0276 (8) | 0.0255 (8) | 0.0223 (8) | 0.0011 (7) | 0.0025 (6) | 0.0077 (6) |
C18 | 0.0244 (8) | 0.0383 (9) | 0.0188 (8) | 0.0016 (7) | 0.0021 (6) | −0.0005 (7) |
Geometric parameters (Å, º) top
O1—C1 | 1.3547 (18) | C7—H7 | 0.9500 |
O1—C8 | 1.3714 (18) | C8—C9 | 1.402 (2) |
O2—C3 | 1.2364 (17) | C10—H10A | 0.9900 |
O3—C4 | 1.3712 (18) | C10—H10B | 0.9900 |
O3—C18 | 1.4358 (19) | C11—C16 | 1.389 (2) |
O4—C5 | 1.3772 (18) | C11—C12 | 1.407 (2) |
O4—C10 | 1.4366 (19) | C12—C13 | 1.396 (2) |
O5—C6 | 1.3759 (17) | C13—C14 | 1.385 (2) |
O5—C10 | 1.4425 (19) | C13—H13 | 0.9500 |
O6—C12 | 1.3715 (18) | C14—C15 | 1.384 (2) |
O6—C17 | 1.4364 (18) | C14—H14 | 0.9500 |
C1—C2 | 1.342 (2) | C15—C16 | 1.391 (2) |
C1—H1 | 0.9500 | C15—H15 | 0.9500 |
C2—C3 | 1.461 (2) | C16—H16 | 0.9500 |
C2—C11 | 1.494 (2) | C17—H17A | 0.9800 |
C3—C9 | 1.478 (2) | C17—H17B | 0.9800 |
C4—C5 | 1.371 (2) | C17—H17C | 0.9800 |
C4—C9 | 1.431 (2) | C18—H18A | 0.9800 |
C5—C6 | 1.389 (2) | C18—H18B | 0.9800 |
C6—C7 | 1.363 (2) | C18—H18C | 0.9800 |
C7—C8 | 1.403 (2) | | |
| | | |
C1—O1—C8 | 118.70 (11) | O5—C10—H10A | 110.3 |
C4—O3—C18 | 114.63 (11) | O4—C10—H10B | 110.3 |
C5—O4—C10 | 104.67 (11) | O5—C10—H10B | 110.3 |
C6—O5—C10 | 104.64 (11) | H10A—C10—H10B | 108.6 |
C12—O6—C17 | 116.46 (11) | C16—C11—C12 | 118.77 (13) |
C2—C1—O1 | 124.54 (13) | C16—C11—C2 | 120.03 (13) |
C2—C1—H1 | 117.7 | C12—C11—C2 | 121.20 (13) |
O1—C1—H1 | 117.7 | O6—C12—C13 | 124.01 (13) |
C1—C2—C3 | 120.23 (13) | O6—C12—C11 | 115.90 (12) |
C1—C2—C11 | 119.22 (13) | C13—C12—C11 | 120.09 (13) |
C3—C2—C11 | 120.42 (12) | C14—C13—C12 | 119.63 (14) |
O2—C3—C2 | 121.48 (13) | C14—C13—H13 | 120.2 |
O2—C3—C9 | 123.79 (13) | C12—C13—H13 | 120.2 |
C2—C3—C9 | 114.72 (12) | C15—C14—C13 | 121.04 (14) |
C5—C4—O3 | 118.10 (13) | C15—C14—H14 | 119.5 |
C5—C4—C9 | 117.58 (13) | C13—C14—H14 | 119.5 |
O3—C4—C9 | 124.26 (13) | C14—C15—C16 | 119.14 (14) |
C4—C5—O4 | 127.75 (13) | C14—C15—H15 | 120.4 |
C4—C5—C6 | 122.54 (14) | C16—C15—H15 | 120.4 |
O4—C5—C6 | 109.66 (12) | C11—C16—C15 | 121.25 (14) |
C7—C6—O5 | 127.82 (13) | C11—C16—H16 | 119.4 |
C7—C6—C5 | 122.59 (13) | C15—C16—H16 | 119.4 |
O5—C6—C5 | 109.56 (13) | O6—C17—H17A | 109.5 |
C6—C7—C8 | 115.21 (13) | O6—C17—H17B | 109.5 |
C6—C7—H7 | 122.4 | H17A—C17—H17B | 109.5 |
C8—C7—H7 | 122.4 | O6—C17—H17C | 109.5 |
O1—C8—C9 | 122.02 (13) | H17A—C17—H17C | 109.5 |
O1—C8—C7 | 113.30 (12) | H17B—C17—H17C | 109.5 |
C9—C8—C7 | 124.67 (13) | O3—C18—H18A | 109.5 |
C8—C9—C4 | 117.40 (13) | O3—C18—H18B | 109.5 |
C8—C9—C3 | 119.12 (13) | H18A—C18—H18B | 109.5 |
C4—C9—C3 | 123.46 (13) | O3—C18—H18C | 109.5 |
O4—C10—O5 | 106.94 (12) | H18A—C18—H18C | 109.5 |
O4—C10—H10A | 110.3 | H18B—C18—H18C | 109.5 |
| | | |
C9—C4—O3—C18 | 76.51 (17) | C11—C12—O6—C17 | −172.77 (12) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C18—H18A···O2 | 0.98 | 2.32 | 2.988 (2) | 124 |
C1—H1···O2i | 0.95 | 2.41 | 3.3393 (19) | 165 |
C7—H7···O5ii | 0.95 | 2.55 | 3.4276 (19) | 153 |
C13—H13···O2iii | 0.95 | 2.59 | 3.496 (2) | 158 |
C15—H15···O4iv | 0.95 | 2.60 | 3.377 (2) | 139 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+2, −y+2, −z+1; (iii) −x+1, −y+2, −z; (iv) x−1, y, z. |