organic compounds
Aca Crystallographica Strtion E
Structure Reports Online
lssN 'r 600-5368
6-l(2P,-3,7-D imethylocta-2,6-dien- 1 -yll- 5,7-dihydroxy-B-(2-methyl butanoyl)-4- phenyl-2H-ch romen-2-one-6 -l(2O -3,7 - dimethylocta-2,6-dien-1 -yll-5,7-
d i hydroxy-8-(3-methylbutano yl)-4- phenyl-2H-chromen-2-one (1/1 ) from
Mesua elegansl
Gomathi Chan,'Khalijah Awang,' Nor Hadiani tsmail,b Seik Weng Ng''' and Edward R. T. Tiekink'*
'Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, bFaculty of Applied Sciences, Universiti Teknologi MARA, 40450 Shah Alam, Malaysia, and themistry Department, Faculty of, Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
Correpondence e-mail: edward.tiekink@gmail com Rtreived 23 February 2012; accepted 27 February 20l2
Key indicators: singlecrystal X-ray study; f = I OO K; mean d(C-C) = O.OO: A;
disorder in main residue; R factor = 0 066; wR factor = 0.208; data-to-parameter ntio = 14 7.
The title co-crystal, C30H3rOs.C3oH:+Os, comprises a 1:1 mixture of two mostly superimposed molecules with the same chemical formula that differ in the nature of the substituent (2-methylbutanoyl or 3-methylbutanoyl) bound at the exocyclic ketone. The lactone ring is close to planar (r.m.s.
deviation = 0.b58 A) anO the phenyl ring is twisted out of this plane [dihedral angle = 60.08 (9)"]. The geranyl substituent is almost normal to benzene ring to which it is connected [C- C-C.,-C* (ar = aromatic) torsion angle = -87.8 (2)'].
Intramolecular O-H. . .O and O-H..'n interactions are formed. In the crystal, supramolecular chains are formed along the a axis owing to C-H' . .O contacts, with the lactone carbonyl atom accepting two such bonds.
Related literature
For the spectroscopic characterization of the title material, see: Verotta et al. (2004) and for its acetylcholinesterase (AChE) inhibitory properties, see: Awang et al. (2010).
I Additional correspondence author, e-mail: khalijah@um.edu.my.
Experimental
Crystal dan cilI{yo5.qoHaos M, = 949.74 Tiiclinic, P1 a = 5.9426 Q) A b = 13.4688 (s) A c = 16.32:75 (6) A a = 91.955 (3)"
d = ee.51s (3)' Data collection Agilent SuperNova Dual
diffractometer with an Atlas detector
Absorption conection: multi-scan (CrysAlis PRO; Agilent, 2011) T^t = 0.826, T-.' = 0.968 Refinement
R [ F 2 > 2 d ( F 2 ) ] = 0 . 0 6 6 rR(F2) = 9.293 s = 1.01 5330 reflections 363 parameters 54 restraints
Table 1
Hydrogen-bond geometry (A, ").
Cgl is the centroid of the C10-C15 ring.
/ = es.834 (3)" . ^ v = 1280.47 (8) N z = l
Cu I(a radiation p = 0.66 mm-r T = 1 0 0 K
0.30 x 0.15 x 0.05 mm
25960 measured reflections 5330 independent reflections 4528 reflections with 1 > 2o(1) Rinr = 0.M5
H atoms treated by a mixture of independent and constrained refinement
A4"., = 0.57 e A-3 - A P m ' = - 0 . 5 3 e A - '
D _ H . . . 4 D - H H . . A D . . . A D _ H . . . 4 O 4 - H 4 o . . . O 5
O 4 - H 4 o . . . O 5 ' O3-II3o-.-Cg|
c2-tr2. .o2' c15-Hl5...02'
t ? < / ? \
z.ss (3) 3.3ss (2)
3.408 (2) 3s57 (z',) 0 8s (1)
0.8s (1) 0.&{ (2)
U.9J
0.95
1s8 (4) 1s4 (3) 158 (4) 169 137 7.s4 (4)
r.76 (4) 2.s6 (4) 2.47 2.59
Symmetry codes: (i) -r + 3, -y + 1, -z + 1; (ii) -x + 2, -y + t, -z + t.
Data collection; CrysAlis PRO (Agilent, 2011); cell refinement:
CrysAlis PRO; data reduction: CrysAlis PRO; ptogram(s) used to solve structure: SHELXS9T (Sheldrick, 2008); program(s) used to refine structure:. SHELXL9T (Sheldrick, 2008); molecular graphics:
ORTEP-3 (Famrgia, 1997) and DIAMOND (Brandenburg, 2006);
software used to prepare material for publication: publCIF (Westip, 2010).
The authors thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High- Impact Research scheme (UM.C/HIR/MOHE/SCy12), Ministry of Science and Technology grant (02-01-01-SF0329) and University of Malaya student's grant (PPP 369/2010B) for the isolation and elucidation of the co-crystal.
Acta Cryst. (2012'). E68, o939-o940 d o i : 1 0 . 1 1 0 7 l S 1 6 0 0 5 3 6 8 1 2 0 0 8 6 2 8 Chan et al. 0939
