The title compound, 1-[2-hydroxy-4-methoxy-5-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one (also known as bavachalcone), C
21H
22O
4, is a polymorphic form of a previously reported structure [Bhalla
et al. (1968).
Tetrahedron Lett.
20, 2401–2406]. The molecules in both polymorphs exhibit nearly identical conformations. In each polymorph, strong intra- and intermolecular hydrogen-bonded chains, involving the hydroxyl groups, are formed. A weak C—H
O interaction is seen in the present structure, but was not observed in the previously reported polymorph.
Supporting information
CCDC reference: 270243
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.002 Å
- R factor = 0.053
- wR factor = 0.158
- Data-to-parameter ratio = 18.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C18
PLAT480_ALERT_4_C Long H...A H-Bond Reported H17 .. O2 .. 2.70 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: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).
1-[2-hydroxy-4-methoxy-5-(3-methylbut-2-enyl)phenyl]-3-(4-hydroxyphenyl)prop-
2-en-1-one
top
Crystal data top
C21H22O4 | F(000) = 720 |
Mr = 338.39 | Dx = 1.214 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5568 reflections |
a = 7.5025 (5) Å | θ = 2.6–27.0° |
b = 22.5080 (15) Å | µ = 0.08 mm−1 |
c = 11.1960 (7) Å | T = 273 K |
β = 101.639 (1)° | Needle, orange |
V = 1851.8 (2) Å3 | 0.30 × 0.18 × 0.11 mm |
Z = 4 | |
Data collection top
CCD Area Detector diffractometer | 3210 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.020 |
Graphite monochromator | θmax = 28.0°, θmin = 1.8° |
ω scans | h = −9→9 |
15814 measured reflections | k = −28→29 |
4328 independent reflections | l = −14→14 |
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.158 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0863P)2 + 0.191P] where P = (Fo2 + 2Fc2)/3 |
4328 reflections | (Δ/σ)max = 0.001 |
231 parameters | Δρmax = 0.26 e Å−3 |
0 restraints | Δρmin = −0.15 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.93913 (17) | 0.56235 (4) | 0.21775 (10) | 0.0721 (3) | |
O2 | 0.80513 (18) | 0.63025 (4) | 0.04795 (10) | 0.0719 (3) | |
H2A | 0.8622 | 0.6201 | 0.1152 | 0.108* | |
O3 | 1.2333 (2) | 0.23790 (5) | 0.56933 (11) | 0.0921 (5) | |
H3 | 1.2124 | 0.2090 | 0.5242 | 0.138* | |
O4 | 0.48216 (16) | 0.54349 (5) | −0.32069 (10) | 0.0719 (3) | |
C1 | 1.0777 (2) | 0.34042 (6) | 0.31741 (12) | 0.0557 (3) | |
H1 | 1.0414 | 0.3399 | 0.2329 | 0.067* | |
C2 | 1.1304 (2) | 0.28837 (6) | 0.37819 (13) | 0.0609 (4) | |
H2 | 1.1310 | 0.2532 | 0.3347 | 0.073* | |
C3 | 1.1826 (2) | 0.28814 (6) | 0.50438 (13) | 0.0608 (4) | |
C4 | 1.1857 (2) | 0.34084 (7) | 0.56738 (13) | 0.0668 (4) | |
H4 | 1.2220 | 0.3412 | 0.6519 | 0.080* | |
C5 | 1.1356 (2) | 0.39271 (6) | 0.50595 (13) | 0.0607 (4) | |
H5 | 1.1405 | 0.4280 | 0.5497 | 0.073* | |
C6 | 1.07762 (18) | 0.39404 (6) | 0.37976 (12) | 0.0502 (3) | |
C7 | 1.0223 (2) | 0.45003 (6) | 0.31922 (13) | 0.0550 (3) | |
H7 | 1.0503 | 0.4841 | 0.3661 | 0.066* | |
C8 | 0.9365 (2) | 0.45818 (6) | 0.20486 (13) | 0.0554 (3) | |
H8 | 0.9048 | 0.4251 | 0.1552 | 0.066* | |
C9 | 0.8897 (2) | 0.51742 (6) | 0.15390 (13) | 0.0536 (3) | |
C10 | 0.78545 (19) | 0.52406 (5) | 0.02972 (12) | 0.0494 (3) | |
C11 | 0.7430 (2) | 0.58132 (5) | −0.01834 (13) | 0.0534 (3) | |
C12 | 0.6389 (2) | 0.58928 (6) | −0.13391 (13) | 0.0556 (3) | |
H12 | 0.6082 | 0.6274 | −0.1632 | 0.067* | |
C13 | 0.58063 (19) | 0.54042 (6) | −0.20554 (13) | 0.0536 (3) | |
C14 | 0.62374 (19) | 0.48215 (6) | −0.16250 (13) | 0.0537 (3) | |
C15 | 0.72286 (19) | 0.47579 (6) | −0.04657 (13) | 0.0514 (3) | |
H15 | 0.7502 | 0.4376 | −0.0168 | 0.062* | |
C16 | 0.5641 (3) | 0.43009 (6) | −0.24531 (16) | 0.0748 (5) | |
H16A | 0.4398 | 0.4368 | −0.2880 | 0.090* | |
H16B | 0.6397 | 0.4284 | −0.3060 | 0.090* | |
C17 | 0.5731 (2) | 0.37133 (6) | −0.18241 (16) | 0.0668 (4) | |
H17 | 0.5227 | 0.3699 | −0.1131 | 0.080* | |
C18 | 0.6432 (2) | 0.32150 (7) | −0.21259 (15) | 0.0681 (4) | |
C19 | 0.6263 (4) | 0.26485 (8) | −0.1447 (2) | 0.1055 (7) | |
H19A | 0.5603 | 0.2724 | −0.0812 | 0.158* | |
H19B | 0.7455 | 0.2502 | −0.1095 | 0.158* | |
H19C | 0.5624 | 0.2358 | −0.2001 | 0.158* | |
C20 | 0.7356 (4) | 0.31540 (10) | −0.3181 (2) | 0.1080 (8) | |
H20A | 0.7712 | 0.3539 | −0.3416 | 0.162* | |
H20B | 0.6537 | 0.2975 | −0.3854 | 0.162* | |
H20C | 0.8416 | 0.2908 | −0.2951 | 0.162* | |
C21 | 0.4255 (3) | 0.60019 (8) | −0.37100 (17) | 0.0791 (5) | |
H21A | 0.5305 | 0.6233 | −0.3777 | 0.119* | |
H21B | 0.3581 | 0.6203 | −0.3188 | 0.119* | |
H21C | 0.3498 | 0.5951 | −0.4504 | 0.119* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.1065 (9) | 0.0460 (6) | 0.0590 (6) | 0.0034 (5) | 0.0052 (6) | −0.0082 (5) |
O2 | 0.1073 (9) | 0.0365 (5) | 0.0673 (7) | 0.0017 (5) | 0.0070 (6) | −0.0040 (4) |
O3 | 0.1522 (13) | 0.0476 (6) | 0.0630 (7) | 0.0041 (7) | −0.0105 (7) | 0.0071 (5) |
O4 | 0.0863 (8) | 0.0547 (6) | 0.0654 (7) | 0.0067 (5) | −0.0069 (5) | 0.0092 (5) |
C1 | 0.0711 (9) | 0.0487 (7) | 0.0440 (7) | −0.0016 (6) | 0.0037 (6) | −0.0030 (6) |
C2 | 0.0825 (10) | 0.0427 (7) | 0.0533 (8) | −0.0042 (6) | 0.0035 (7) | −0.0085 (6) |
C3 | 0.0775 (10) | 0.0434 (7) | 0.0558 (8) | −0.0022 (6) | 0.0005 (7) | 0.0027 (6) |
C4 | 0.0941 (11) | 0.0562 (8) | 0.0434 (7) | 0.0029 (8) | −0.0022 (7) | −0.0035 (6) |
C5 | 0.0809 (10) | 0.0466 (7) | 0.0498 (7) | 0.0052 (7) | 0.0019 (7) | −0.0084 (6) |
C6 | 0.0553 (7) | 0.0456 (7) | 0.0480 (7) | 0.0003 (5) | 0.0064 (5) | −0.0024 (5) |
C7 | 0.0664 (8) | 0.0447 (7) | 0.0530 (8) | 0.0045 (6) | 0.0101 (6) | −0.0038 (6) |
C8 | 0.0708 (9) | 0.0428 (7) | 0.0519 (7) | 0.0005 (6) | 0.0110 (6) | −0.0001 (6) |
C9 | 0.0671 (8) | 0.0437 (7) | 0.0516 (7) | 0.0030 (6) | 0.0155 (6) | −0.0015 (6) |
C10 | 0.0600 (8) | 0.0380 (6) | 0.0520 (7) | 0.0036 (5) | 0.0155 (6) | 0.0009 (5) |
C11 | 0.0678 (8) | 0.0361 (6) | 0.0591 (8) | 0.0032 (6) | 0.0194 (6) | −0.0006 (5) |
C12 | 0.0668 (8) | 0.0382 (6) | 0.0634 (8) | 0.0079 (6) | 0.0168 (7) | 0.0077 (6) |
C13 | 0.0560 (8) | 0.0473 (7) | 0.0570 (8) | 0.0047 (6) | 0.0100 (6) | 0.0061 (6) |
C14 | 0.0603 (8) | 0.0404 (6) | 0.0584 (8) | 0.0021 (6) | 0.0075 (6) | −0.0005 (6) |
C15 | 0.0632 (8) | 0.0351 (6) | 0.0555 (7) | 0.0042 (5) | 0.0114 (6) | 0.0033 (5) |
C16 | 0.0964 (12) | 0.0467 (8) | 0.0690 (10) | 0.0002 (7) | −0.0128 (9) | −0.0038 (7) |
C17 | 0.0755 (10) | 0.0483 (8) | 0.0720 (10) | −0.0073 (7) | 0.0043 (8) | −0.0038 (7) |
C18 | 0.0753 (10) | 0.0483 (8) | 0.0745 (10) | 0.0008 (7) | 0.0005 (8) | 0.0000 (7) |
C19 | 0.1276 (18) | 0.0540 (10) | 0.1344 (19) | 0.0016 (11) | 0.0254 (15) | 0.0178 (11) |
C20 | 0.148 (2) | 0.0847 (14) | 0.0940 (15) | 0.0314 (13) | 0.0309 (14) | 0.0016 (12) |
C21 | 0.0805 (11) | 0.0665 (10) | 0.0821 (11) | 0.0058 (8) | −0.0036 (9) | 0.0267 (9) |
Geometric parameters (Å, º) top
O1—C9 | 1.2506 (16) | C10—C11 | 1.4081 (17) |
O2—C11 | 1.3570 (16) | C11—C12 | 1.382 (2) |
O2—H2A | 0.8200 | C12—C13 | 1.379 (2) |
O3—C3 | 1.3568 (17) | C12—H12 | 0.9300 |
O3—H3 | 0.8200 | C13—C14 | 1.4121 (18) |
O4—C13 | 1.3521 (17) | C14—C15 | 1.3670 (19) |
O4—C21 | 1.4248 (18) | C14—C16 | 1.5053 (19) |
C1—C2 | 1.3723 (19) | C15—H15 | 0.9300 |
C1—C6 | 1.3943 (18) | C16—C17 | 1.493 (2) |
C1—H1 | 0.9300 | C16—H16A | 0.9700 |
C2—C3 | 1.388 (2) | C16—H16B | 0.9700 |
C2—H2 | 0.9300 | C17—C18 | 1.312 (2) |
C3—C4 | 1.378 (2) | C17—H17 | 0.9300 |
C4—C5 | 1.369 (2) | C18—C20 | 1.492 (3) |
C4—H4 | 0.9300 | C18—C19 | 1.503 (2) |
C5—C6 | 1.3922 (18) | C19—H19A | 0.9600 |
C5—H5 | 0.9300 | C19—H19B | 0.9600 |
C6—C7 | 1.4514 (18) | C19—H19C | 0.9600 |
C7—C8 | 1.3246 (19) | C20—H20A | 0.9600 |
C7—H7 | 0.9300 | C20—H20B | 0.9600 |
C8—C9 | 1.4649 (18) | C20—H20C | 0.9600 |
C8—H8 | 0.9300 | C21—H21A | 0.9600 |
C9—C10 | 1.4588 (19) | C21—H21B | 0.9600 |
C10—C15 | 1.4033 (18) | C21—H21C | 0.9600 |
| | | |
C11—O2—H2A | 109.5 | O4—C13—C12 | 124.18 (12) |
C3—O3—H3 | 109.5 | O4—C13—C14 | 114.60 (12) |
C13—O4—C21 | 118.99 (13) | C12—C13—C14 | 121.21 (13) |
C2—C1—C6 | 121.32 (12) | C15—C14—C13 | 117.69 (12) |
C2—C1—H1 | 119.3 | C15—C14—C16 | 122.71 (12) |
C6—C1—H1 | 119.3 | C13—C14—C16 | 119.58 (13) |
C1—C2—C3 | 120.13 (12) | C14—C15—C10 | 123.23 (12) |
C1—C2—H2 | 119.9 | C14—C15—H15 | 118.4 |
C3—C2—H2 | 119.9 | C10—C15—H15 | 118.4 |
O3—C3—C4 | 117.98 (13) | C17—C16—C14 | 114.80 (14) |
O3—C3—C2 | 122.67 (13) | C17—C16—H16A | 108.6 |
C4—C3—C2 | 119.34 (13) | C14—C16—H16A | 108.6 |
C5—C4—C3 | 120.17 (13) | C17—C16—H16B | 108.6 |
C5—C4—H4 | 119.9 | C14—C16—H16B | 108.6 |
C3—C4—H4 | 119.9 | H16A—C16—H16B | 107.5 |
C4—C5—C6 | 121.75 (13) | C18—C17—C16 | 128.19 (18) |
C4—C5—H5 | 119.1 | C18—C17—H17 | 115.9 |
C6—C5—H5 | 119.1 | C16—C17—H17 | 115.9 |
C5—C6—C1 | 117.25 (12) | C17—C18—C20 | 123.87 (17) |
C5—C6—C7 | 119.61 (12) | C17—C18—C19 | 121.10 (18) |
C1—C6—C7 | 123.14 (12) | C20—C18—C19 | 114.97 (17) |
C8—C7—C6 | 127.53 (13) | C18—C19—H19A | 109.5 |
C8—C7—H7 | 116.2 | C18—C19—H19B | 109.5 |
C6—C7—H7 | 116.2 | H19A—C19—H19B | 109.5 |
C7—C8—C9 | 122.28 (13) | C18—C19—H19C | 109.5 |
C7—C8—H8 | 118.9 | H19A—C19—H19C | 109.5 |
C9—C8—H8 | 118.9 | H19B—C19—H19C | 109.5 |
O1—C9—C10 | 120.14 (12) | C18—C20—H20A | 109.5 |
O1—C9—C8 | 119.55 (13) | C18—C20—H20B | 109.5 |
C10—C9—C8 | 120.31 (12) | H20A—C20—H20B | 109.5 |
C15—C10—C11 | 117.00 (13) | C18—C20—H20C | 109.5 |
C15—C10—C9 | 123.37 (11) | H20A—C20—H20C | 109.5 |
C11—C10—C9 | 119.63 (12) | H20B—C20—H20C | 109.5 |
O2—C11—C12 | 118.29 (12) | O4—C21—H21A | 109.5 |
O2—C11—C10 | 120.51 (13) | O4—C21—H21B | 109.5 |
C12—C11—C10 | 121.20 (12) | H21A—C21—H21B | 109.5 |
C13—C12—C11 | 119.62 (12) | O4—C21—H21C | 109.5 |
C13—C12—H12 | 120.2 | H21A—C21—H21C | 109.5 |
C11—C12—H12 | 120.2 | H21B—C21—H21C | 109.5 |
| | | |
C6—C1—C2—C3 | 0.9 (3) | C15—C10—C11—C12 | 2.2 (2) |
C1—C2—C3—O3 | 179.02 (15) | C9—C10—C11—C12 | −177.59 (12) |
C1—C2—C3—C4 | −1.7 (3) | O2—C11—C12—C13 | 177.13 (13) |
O3—C3—C4—C5 | −179.95 (16) | C10—C11—C12—C13 | −2.4 (2) |
C2—C3—C4—C5 | 0.8 (3) | C21—O4—C13—C12 | −3.3 (2) |
C3—C4—C5—C6 | 1.1 (3) | C21—O4—C13—C14 | 177.59 (13) |
C4—C5—C6—C1 | −1.9 (2) | C11—C12—C13—O4 | −178.31 (13) |
C4—C5—C6—C7 | 178.70 (14) | C11—C12—C13—C14 | 0.7 (2) |
C2—C1—C6—C5 | 0.9 (2) | O4—C13—C14—C15 | −179.87 (12) |
C2—C1—C6—C7 | −179.71 (14) | C12—C13—C14—C15 | 1.0 (2) |
C5—C6—C7—C8 | −167.96 (15) | O4—C13—C14—C16 | 1.6 (2) |
C1—C6—C7—C8 | 12.7 (2) | C12—C13—C14—C16 | −177.53 (15) |
C6—C7—C8—C9 | −179.30 (13) | C13—C14—C15—C10 | −1.1 (2) |
C7—C8—C9—O1 | 3.4 (2) | C16—C14—C15—C10 | 177.37 (15) |
C7—C8—C9—C10 | −176.27 (13) | C11—C10—C15—C14 | −0.5 (2) |
O1—C9—C10—C15 | −178.95 (14) | C9—C10—C15—C14 | 179.37 (13) |
C8—C9—C10—C15 | 0.8 (2) | C15—C14—C16—C17 | 16.7 (2) |
O1—C9—C10—C11 | 0.9 (2) | C13—C14—C16—C17 | −164.79 (15) |
C8—C9—C10—C11 | −179.41 (13) | C14—C16—C17—C18 | −132.30 (19) |
C15—C10—C11—O2 | −177.26 (13) | C16—C17—C18—C20 | 2.1 (3) |
C9—C10—C11—O2 | 2.9 (2) | C16—C17—C18—C19 | −174.69 (17) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2A···O1 | 0.82 | 1.75 | 2.488 (2) | 148 |
O3—H3···O2i | 0.82 | 1.94 | 2.743 (2) | 166 |
C17—H17···O2ii | 0.93 | 2.70 | 3.470 (2) | 140 |
Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) −x+1, −y+1, −z. |