The title compound [systematic name: 5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,6,7-trimethoxychromen-4-one (casticin)], C
19H
18O
8, was isolated from the seeds of
Vitex agnus-castus L. The fused chromene ring system and the benzene ring bonded to it are close to coplanar, with a dihedral angle between their respective mean planes of 8.30 (12)°. The two hydroxy H atoms are involved in intramolecular O—H
O hydrogen bonding. Intermolecular O—H
O and C—H
O hydrogen bonds and π–π interactions help to stabilize the crystal structure.
Supporting information
CCDC reference: 621335
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.004 Å
- R factor = 0.094
- wR factor = 0.215
- Data-to-parameter ratio = 13.5
checkCIF/PLATON results
No syntax errors found
Alert level B
DIFMX01_ALERT_2_B The maximum difference density is > 0.1*ZMAX*1.00
_refine_diff_density_max given = 0.983
Test value = 0.800
PLAT097_ALERT_2_B Maximum (Positive) Residual Density ............ 0.98 e/A
Alert level C
DIFMN02_ALERT_2_C The minimum difference density is < -0.1*ZMAX*0.75
_refine_diff_density_min given = -0.709
Test value = -0.600
DIFMN03_ALERT_1_C The minimum difference density is < -0.1*ZMAX*0.75
The relevant atom site should be identified.
DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75
The relevant atom site should be identified.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.96
PLAT098_ALERT_2_C Minimum (Negative) Residual Density ............ -0.71 e/A
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.06
0 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
5 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999).
5-hydroxy-2-(3-hydroxy-4-methoxyphenyl)-3,6,7-trimethoxychromen-4-one
top
Crystal data top
C19H18O8 | F(000) = 1568 |
Mr = 374.33 | Dx = 1.457 Mg m−3 |
Monoclinic, C2/c | Cu Kα radiation, λ = 1.54184 Å |
Hall symbol: -C 2yc | Cell parameters from 25 reflections |
a = 15.5353 (5) Å | θ = 2.2–19.3° |
b = 12.4493 (3) Å | µ = 0.97 mm−1 |
c = 17.6655 (3) Å | T = 294 K |
β = 92.424 (2)° | Plate, yellow |
V = 3413.51 (15) Å3 | 0.35 × 0.25 × 0.15 mm |
Z = 8 | |
Data collection top
Enraf–Nonius CAD-4 diffractometer | 2259 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.029 |
Graphite monochromator | θmax = 74.3°, θmin = 5.0° |
ω scans | h = 0→19 |
Absorption correction: ψ scan (North et al., 1968) | k = −15→0 |
Tmin = 0.727, Tmax = 0.868 | l = −22→22 |
3463 measured reflections | 3 standard reflections every 120 min |
3350 independent reflections | intensity decay: 1% |
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)] = 0.094 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.216 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.1338P)2 + 0.0496P] where P = (Fo2 + 2Fc2)/3 |
3350 reflections | (Δ/σ)max < 0.001 |
248 parameters | Δρmax = 0.98 e Å−3 |
0 restraints | Δρmin = −0.71 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 | 0.10368 (12) | 0.55315 (14) | 0.22741 (11) | 0.0539 (5) | |
O3 | 0.19321 (14) | 0.61592 (16) | 0.41496 (10) | 0.0579 (5) | |
O3' | 0.10645 (19) | 0.16953 (18) | 0.22228 (12) | 0.0892 (9) | |
H3' | 0.1179 | 0.1082 | 0.2363 | 0.134* | |
O4 | 0.17190 (15) | 0.81631 (16) | 0.35145 (12) | 0.0665 (6) | |
O4' | 0.18957 (13) | 0.09746 (14) | 0.34872 (11) | 0.0618 (6) | |
O5 | 0.13000 (15) | 0.93629 (15) | 0.23552 (12) | 0.0653 (6) | |
H5 | 0.1480 | 0.9219 | 0.2786 | 0.098* | |
O6 | 0.06947 (13) | 0.94623 (15) | 0.08816 (11) | 0.0594 (5) | |
O7 | 0.01526 (15) | 0.76975 (18) | 0.01627 (11) | 0.0675 (6) | |
C1' | 0.15122 (16) | 0.4250 (2) | 0.31602 (14) | 0.0469 (6) | |
C2 | 0.14133 (17) | 0.5402 (2) | 0.29794 (15) | 0.0481 (6) | |
C2' | 0.1221 (2) | 0.3481 (2) | 0.26378 (16) | 0.0562 (7) | |
H2' | 0.0931 | 0.3703 | 0.2194 | 0.067* | |
C3 | 0.16416 (18) | 0.6276 (2) | 0.34138 (15) | 0.0498 (6) | |
C3' | 0.1350 (2) | 0.2404 (2) | 0.27612 (15) | 0.0552 (7) | |
C4 | 0.15238 (18) | 0.7355 (2) | 0.31235 (14) | 0.0512 (7) | |
C4A | 0.11771 (18) | 0.7439 (2) | 0.23618 (15) | 0.0491 (6) | |
C4' | 0.17743 (18) | 0.2058 (2) | 0.34243 (15) | 0.0507 (6) | |
C5 | 0.10608 (18) | 0.8445 (2) | 0.19899 (17) | 0.0531 (7) | |
C5' | 0.2051 (2) | 0.2807 (3) | 0.39475 (18) | 0.0712 (9) | |
H5' | 0.2328 | 0.2581 | 0.4397 | 0.085* | |
C6 | 0.07368 (18) | 0.8500 (2) | 0.12555 (17) | 0.0524 (7) | |
C6' | 0.1926 (2) | 0.3893 (2) | 0.38205 (18) | 0.0689 (9) | |
H6' | 0.2123 | 0.4387 | 0.4183 | 0.083* | |
C7 | 0.04725 (19) | 0.7549 (2) | 0.08729 (15) | 0.0532 (7) | |
C8 | 0.05691 (18) | 0.6554 (2) | 0.12288 (16) | 0.0533 (7) | |
H8 | 0.0396 | 0.5924 | 0.0983 | 0.064* | |
C8A | 0.09290 (17) | 0.65286 (19) | 0.19558 (16) | 0.0485 (6) | |
C9 | 0.2811 (2) | 0.6472 (3) | 0.4300 (2) | 0.0712 (9) | |
H9A | 0.3186 | 0.5960 | 0.4077 | 0.107* | |
H9B | 0.2929 | 0.6496 | 0.4838 | 0.107* | |
H9C | 0.2905 | 0.7169 | 0.4087 | 0.107* | |
C10 | −0.0086 (2) | 1.0028 (2) | 0.0993 (2) | 0.0684 (9) | |
H10A | −0.0566 | 0.9595 | 0.0820 | 0.103* | |
H10B | −0.0086 | 1.0688 | 0.0712 | 0.103* | |
H10C | −0.0132 | 1.0183 | 0.1522 | 0.103* | |
C11 | −0.0158 (2) | 0.6789 (3) | −0.02594 (19) | 0.0759 (10) | |
H11A | 0.0297 | 0.6271 | −0.0295 | 0.114* | |
H11B | −0.0348 | 0.7013 | −0.0759 | 0.114* | |
H11C | −0.0631 | 0.6471 | −0.0008 | 0.114* | |
C12 | 0.2265 (2) | 0.0586 (3) | 0.41885 (19) | 0.0689 (9) | |
H12A | 0.2820 | 0.0908 | 0.4282 | 0.103* | |
H12B | 0.2326 | −0.0181 | 0.4163 | 0.103* | |
H12C | 0.1896 | 0.0768 | 0.4592 | 0.103* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0731 (12) | 0.0356 (9) | 0.0519 (11) | 0.0036 (8) | −0.0093 (9) | 0.0065 (7) |
O3 | 0.0803 (14) | 0.0478 (10) | 0.0451 (10) | 0.0007 (10) | −0.0013 (9) | 0.0013 (8) |
O3' | 0.166 (3) | 0.0435 (11) | 0.0545 (13) | 0.0044 (13) | −0.0329 (14) | −0.0013 (9) |
O4 | 0.1020 (16) | 0.0401 (10) | 0.0564 (12) | 0.0116 (10) | −0.0085 (11) | −0.0040 (8) |
O4' | 0.0871 (15) | 0.0381 (10) | 0.0589 (12) | −0.0021 (9) | −0.0132 (10) | 0.0118 (8) |
O5 | 0.0985 (16) | 0.0363 (10) | 0.0604 (12) | 0.0056 (10) | −0.0062 (11) | 0.0021 (8) |
O6 | 0.0700 (13) | 0.0443 (10) | 0.0638 (13) | 0.0049 (9) | 0.0042 (10) | 0.0191 (9) |
O7 | 0.0933 (16) | 0.0552 (12) | 0.0528 (12) | 0.0040 (11) | −0.0109 (11) | 0.0104 (9) |
C1' | 0.0542 (15) | 0.0410 (13) | 0.0454 (13) | 0.0011 (10) | 0.0012 (11) | 0.0060 (10) |
C2 | 0.0572 (16) | 0.0431 (14) | 0.0439 (13) | 0.0053 (11) | 0.0026 (11) | 0.0053 (11) |
C2' | 0.080 (2) | 0.0450 (15) | 0.0432 (14) | 0.0052 (13) | −0.0055 (13) | 0.0061 (11) |
C3 | 0.0630 (16) | 0.0417 (13) | 0.0447 (14) | 0.0052 (12) | 0.0012 (12) | 0.0027 (11) |
C3' | 0.0791 (19) | 0.0421 (14) | 0.0440 (14) | −0.0004 (13) | −0.0021 (13) | 0.0017 (11) |
C4 | 0.0638 (17) | 0.0398 (14) | 0.0500 (15) | 0.0088 (11) | 0.0040 (12) | −0.0001 (11) |
C4A | 0.0582 (16) | 0.0381 (13) | 0.0512 (14) | 0.0075 (11) | 0.0050 (12) | 0.0046 (10) |
C4' | 0.0638 (17) | 0.0379 (13) | 0.0501 (14) | −0.0040 (12) | −0.0008 (12) | 0.0099 (11) |
C5 | 0.0644 (18) | 0.0386 (14) | 0.0566 (17) | 0.0068 (11) | 0.0055 (13) | 0.0020 (11) |
C5' | 0.102 (3) | 0.0464 (16) | 0.0628 (18) | −0.0072 (16) | −0.0308 (17) | 0.0140 (13) |
C6 | 0.0611 (16) | 0.0410 (14) | 0.0554 (16) | 0.0065 (11) | 0.0063 (13) | 0.0121 (11) |
C6' | 0.100 (2) | 0.0437 (15) | 0.0605 (18) | −0.0122 (16) | −0.0229 (16) | 0.0058 (13) |
C7 | 0.0607 (16) | 0.0476 (15) | 0.0509 (15) | 0.0047 (12) | −0.0006 (12) | 0.0085 (12) |
C8 | 0.0629 (17) | 0.0419 (14) | 0.0545 (16) | 0.0038 (12) | −0.0032 (13) | 0.0041 (11) |
C8A | 0.0561 (15) | 0.0367 (13) | 0.0529 (15) | 0.0075 (11) | 0.0043 (12) | 0.0082 (10) |
C9 | 0.085 (2) | 0.0581 (19) | 0.069 (2) | 0.0060 (16) | −0.0131 (17) | 0.0013 (14) |
C10 | 0.079 (2) | 0.0496 (17) | 0.077 (2) | 0.0191 (15) | 0.0009 (17) | 0.0155 (15) |
C11 | 0.092 (3) | 0.075 (2) | 0.0584 (19) | −0.0044 (19) | −0.0166 (17) | 0.0034 (16) |
C12 | 0.085 (2) | 0.0437 (15) | 0.076 (2) | −0.0067 (14) | −0.0237 (17) | 0.0199 (14) |
Geometric parameters (Å, º) top
O1—C2 | 1.363 (3) | C4A—C5 | 1.423 (3) |
O1—C8A | 1.370 (3) | C4A—C4 | 1.432 (4) |
O3—C3 | 1.365 (3) | C5—C6 | 1.373 (4) |
O3—C9 | 1.433 (4) | C5'—C6' | 1.383 (4) |
O3'—C3' | 1.358 (3) | C5'—H5' | 0.9300 |
O3'—H3' | 0.8200 | C6'—H6' | 0.9300 |
O4'—C4' | 1.366 (3) | C7—C6 | 1.415 (4) |
O4'—C12 | 1.428 (3) | C8—C8A | 1.379 (4) |
O4—C4 | 1.250 (3) | C8—C7 | 1.395 (4) |
O5—C5 | 1.356 (3) | C8—H8 | 0.9300 |
O5—H5 | 0.8200 | C9—H9A | 0.9600 |
O6—C6 | 1.368 (3) | C9—H9B | 0.9600 |
O6—C10 | 1.424 (3) | C9—H9C | 0.9600 |
O7—C7 | 1.343 (3) | C10—H10A | 0.9600 |
C1'—C6' | 1.382 (4) | C10—H10B | 0.9600 |
C1'—C2' | 1.392 (4) | C10—H10C | 0.9600 |
C1'—C2 | 1.475 (4) | C11—O7 | 1.427 (4) |
C2—C3 | 1.370 (4) | C11—H11A | 0.9600 |
C2'—C3' | 1.372 (4) | C11—H11B | 0.9600 |
C2'—H2' | 0.9300 | C11—H11C | 0.9600 |
C4—C3 | 1.447 (4) | C12—H12A | 0.9600 |
C4'—C5' | 1.369 (4) | C12—H12B | 0.9600 |
C4'—C3' | 1.388 (4) | C12—H12C | 0.9600 |
C4A—C8A | 1.387 (4) | | |
| | | |
C2—O1—C8A | 121.5 (2) | O6—C6—C7 | 119.6 (3) |
C3—O3—C9 | 114.9 (2) | C5—C6—C7 | 119.8 (2) |
C3'—O3'—H3' | 109.5 | C1'—C6'—C5' | 120.6 (3) |
C4'—O4'—C12 | 117.0 (2) | C1'—C6'—H6' | 119.7 |
C5—O5—H5 | 109.5 | C5'—C6'—H6' | 119.7 |
C6—O6—C10 | 113.0 (2) | O7—C7—C8 | 124.9 (3) |
C7—O7—C11 | 118.9 (2) | O7—C7—C6 | 114.8 (2) |
C6'—C1'—C2' | 117.7 (3) | C8—C7—C6 | 120.3 (2) |
C6'—C1'—C2 | 122.4 (3) | C8A—C8—C7 | 118.1 (3) |
C2'—C1'—C2 | 119.8 (2) | C8A—C8—H8 | 120.9 |
O1—C2—C3 | 120.6 (2) | C7—C8—H8 | 120.9 |
O1—C2—C1' | 110.5 (2) | O1—C8A—C8 | 116.1 (2) |
C3—C2—C1' | 129.0 (2) | O1—C8A—C4A | 120.1 (2) |
C3'—C2'—C1' | 121.7 (3) | C8—C8A—C4A | 123.8 (2) |
C3'—C2'—H2' | 119.2 | O3—C9—H9A | 109.5 |
C1'—C2'—H2' | 119.2 | O3—C9—H9B | 109.5 |
O3—C3—C2 | 121.0 (2) | H9A—C9—H9B | 109.5 |
O3—C3—C4 | 117.9 (2) | O3—C9—H9C | 109.5 |
C2—C3—C4 | 120.9 (2) | H9A—C9—H9C | 109.5 |
O3'—C3'—C2' | 118.8 (3) | H9B—C9—H9C | 109.5 |
O3'—C3'—C4' | 121.2 (3) | O6—C10—H10A | 109.5 |
C2'—C3'—C4' | 119.9 (3) | O6—C10—H10B | 109.5 |
O4—C4—C4A | 122.3 (2) | H10A—C10—H10B | 109.5 |
O4—C4—C3 | 121.8 (2) | O6—C10—H10C | 109.5 |
C4A—C4—C3 | 115.9 (2) | H10A—C10—H10C | 109.5 |
C8A—C4A—C5 | 117.0 (2) | H10B—C10—H10C | 109.5 |
C8A—C4A—C4 | 120.8 (2) | O7—C11—H11A | 109.5 |
C5—C4A—C4 | 122.2 (2) | O7—C11—H11B | 109.5 |
O4'—C4'—C5' | 125.4 (2) | H11A—C11—H11B | 109.5 |
O4'—C4'—C3' | 115.7 (2) | O7—C11—H11C | 109.5 |
C5'—C4'—C3' | 118.9 (2) | H11A—C11—H11C | 109.5 |
O5—C5—C6 | 119.3 (2) | H11B—C11—H11C | 109.5 |
O5—C5—C4A | 119.7 (3) | O4'—C12—H12A | 109.5 |
C6—C5—C4A | 121.0 (2) | O4'—C12—H12B | 109.5 |
C4'—C5'—C6' | 121.2 (3) | H12A—C12—H12B | 109.5 |
C4'—C5'—H5' | 119.4 | O4'—C12—H12C | 109.5 |
C6'—C5'—H5' | 119.4 | H12A—C12—H12C | 109.5 |
O6—C6—C5 | 120.5 (3) | H12B—C12—H12C | 109.5 |
| | | |
C2—O1—C8A—C8 | 177.7 (2) | C3'—C4'—C5'—C6' | −1.0 (5) |
C2—O1—C8A—C4A | −2.3 (4) | O4'—C4'—C3'—O3' | 1.2 (4) |
C8A—O1—C2—C3 | 4.6 (4) | C5'—C4'—C3'—O3' | 179.8 (3) |
C8A—O1—C2—C1' | −175.5 (2) | O4'—C4'—C3'—C2' | −178.1 (3) |
C9—O3—C3—C2 | 114.7 (3) | C5'—C4'—C3'—C2' | 0.5 (5) |
C9—O3—C3—C4 | −69.7 (3) | C8A—C4A—C5—O5 | −179.3 (3) |
C12—O4'—C4'—C5' | 6.6 (4) | C4—C4A—C5—O5 | 1.4 (4) |
C12—O4'—C4'—C3' | −174.9 (3) | C8A—C4A—C5—C6 | −1.6 (4) |
C10—O6—C6—C5 | −88.3 (3) | C4—C4A—C5—C6 | 179.2 (3) |
C10—O6—C6—C7 | 94.0 (3) | C8A—C4A—C4—O4 | −176.9 (3) |
C11—O7—C7—C8 | 3.4 (5) | C5—C4A—C4—O4 | 2.3 (4) |
C11—O7—C7—C6 | −177.9 (3) | C8A—C4A—C4—C3 | 3.5 (4) |
C2'—C1'—C6'—C5' | 0.7 (5) | C5—C4A—C4—C3 | −177.2 (3) |
C2—C1'—C6'—C5' | −176.1 (3) | C5—C4A—C8A—O1 | 178.9 (2) |
C6'—C1'—C2—O1 | 175.7 (3) | C4—C4A—C8A—O1 | −1.9 (4) |
C2'—C1'—C2—O1 | −1.0 (4) | C5—C4A—C8A—C8 | −1.1 (4) |
C6'—C1'—C2—C3 | −4.4 (5) | C4—C4A—C8A—C8 | 178.2 (3) |
C2'—C1'—C2—C3 | 178.9 (3) | O5—C5—C6—O6 | 3.2 (4) |
C6'—C1'—C2'—C3' | −1.2 (5) | C4A—C5—C6—O6 | −174.5 (2) |
C2—C1'—C2'—C3' | 175.7 (3) | O5—C5—C6—C7 | −179.0 (2) |
O1—C2—C3—O3 | 172.8 (2) | C4A—C5—C6—C7 | 3.3 (4) |
C1'—C2—C3—O3 | −7.1 (5) | C4'—C5'—C6'—C1' | 0.4 (6) |
O1—C2—C3—C4 | −2.7 (4) | O7—C7—C6—O6 | −3.3 (4) |
C1'—C2—C3—C4 | 177.4 (3) | C8—C7—C6—O6 | 175.4 (3) |
C1'—C2'—C3'—O3' | −178.7 (3) | O7—C7—C6—C5 | 178.9 (2) |
C1'—C2'—C3'—C4' | 0.6 (5) | C8—C7—C6—C5 | −2.4 (5) |
O4—C4—C3—O3 | 3.5 (4) | C7—C8—C8A—O1 | −178.0 (2) |
C4A—C4—C3—O3 | −176.9 (2) | C7—C8—C8A—C4A | 2.0 (4) |
O4—C4—C3—C2 | 179.2 (3) | C8A—C8—C7—O7 | 178.4 (3) |
C4A—C4—C3—C2 | −1.3 (4) | C8A—C8—C7—C6 | −0.2 (4) |
O4'—C4'—C5'—C6' | 177.5 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5···O4 | 0.82 | 1.87 | 2.596 (3) | 148 |
O3′—H3′···O4′ | 0.82 | 2.24 | 2.687 (3) | 115 |
O3′—H3′···O5i | 0.82 | 2.15 | 2.935 (3) | 161 |
O5—H5···O4′ii | 0.82 | 2.58 | 2.954 (3) | 109 |
C10—H10b···O7iii | 0.96 | 2.54 | 3.491 (4) | 173 |
C12—H12b···O4i | 0.96 | 2.52 | 3.339 (4) | 143 |
Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z; (iii) −x, −y+2, −z. |