6-[(2E)-3,7-Dimethyl­octa-2,6-dien-1-yl]-5,7-dihy­droxy-8-(2-methyl­butano­yl)-4-phenyl-2H-chromen-2-one–6-[(2E)-3,7-dimethyl­octa-2,6-dien-1-yl]-5,7-dihy­droxy-8-(3-methyl­butano­yl)-4-phenyl-2H-chromen-2-one (1/1) from Mesua elegans

Chan, G.; Awang, K.; Ismail, N.H.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536812008628

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Pages o939-o940

doi:10.1107/S1600536812008628

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6-[(2E)-3,7-Dimethylocta-2,6-dien-1-yl]-5,7-dihydroxy-8-(2-methylbutanoyl)-4-phenyl-2H-chromen-2-one–6-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-5,7-dihydroxy-8-(3-methylbutanoyl)-4-phenyl-2H-chromen-2-one (1/1) from Mesua elegans¹

Gomathi Chan,^a Khalijah Awang,^a Nor Hadiani Ismail,^b Seik Weng Ng ^a,^c and Edward R. T. Tiekink ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, ^bFaculty of Applied Sciences, Universiti Teknologi MARA, 40450 Shah Alam, Malaysia, and ^cChemistry Department, Faculty of, Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 23 February 2012; accepted 27 February 2012; online 3 March 2012)

The title co-crystal, C₃₀H₃₄O₅·C₃₀H₃₄O₅, 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 = 0.058 Å) and 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_ar—C_ar (ar = aromatic) torsion angle = −87.8 (2)°]. Intramolecular O—H⋯O and O—H⋯π 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 ).

Experimental

Crystal data

C₃₀H₃₄O₅·C₃₀H₃₄O₅
M_r = 949.14
Triclinic, $[P \overline 1]$
a = 5.9426 (2) Å
b = 13.4688 (5) Å
c = 16.3275 (6) Å
α = 91.955 (3)°
β = 99.515 (3)°
γ = 95.834 (3)°
V = 1280.47 (8) Å³
Z = 1
Cu Kα radiation
μ = 0.66 mm⁻¹
T = 100 K
0.30 × 0.15 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.826, T_max = 0.968
25960 measured reflections
5330 independent reflections
4528 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.066
wR(F²) = 0.208
S = 1.01
5330 reflections
363 parameters
54 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.53 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C10–C15 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4o⋯O5	0.85 (1)	1.54 (4)	2.35 (3)	158 (4)
O4—H4o⋯O5′	0.85 (1)	1.76 (4)	2.55 (3)	154 (3)
O3—H3o⋯Cg1	0.84 (2)	2.56 (4)	3.355 (2)	158 (4)
C2—H2⋯O2ⁱ	0.95	2.47	3.408 (2)	169
C15—H15⋯O2ⁱⁱ	0.95	2.59	3.351 (2)	137
Symmetry codes: (i) -x+3, -y+1, -z+1; (ii) -x+2, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812008628/hb6652sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812008628/hb6652Isup2.hkl

checkCIF report

Comment top

The structure of the title co-crystal (I), previously isolated from Mesua ferrea, was elucidated by spectroscopic measurements (Verotta et al., 2004). Both components possess the 4-phenylcoumarin skeleton, which is substituted by two hydroxyl group at C-5 and C-7, and a geranyl group at C-6. The difference between the two compounds is the substituent at position C-8; the first is substituted with 2-methylbutanoyl and the second is substituted with the 3-methyl- butanoyl group. The title co-crystal have been evaluated as multi-drug resistant anti-bacterials (Verotta et al., 2004) and for their acetylcholinesterase (AChE) inhibitory properties (Awang et al., 2010). Herein, a crystallographic analysis is described.

The molecular components of the co-crystal (I) are shown in Figs 1 and 2. The r.m.s. deviation for the fitted atoms of the lactone ring = 0.058 Å with maximum deviations of 0.043 (2) Å for the C3 atoms and -0.058 (2) Å for the C4 atom. The phenyl ring is twisted out of this plane, forming a dihedral angle of 60.08 (9)°. The excocyclic carbonyl atom is co-planar with the benzene ring to which it is connected with the C7—C8—C26—O5 torsion angle being 2.2 (10)°; the equivalent torsion angle for the molecule with the 3-methylbutanoyl is 9.9 (9)°. The co-planarity is readily accounted for in terms of intramolecular O—H···O hydrogen bonds. The geranyl group projects almost normal to the plane through the benzene ring with the C5—C6—C16—C17 torsion angle being -87.8 (2)°. The second hydroxyl group forms an intramolecular O—H···π interaction with the phenyl ring, Table 1.

In the crystal, the lactone-carbonyl atom participates in two C—H···O interactions, Table 1, to link molecules into a supramolecular chain along the a axis, Fig. 3.

Related literature top

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).

Experimental top

Dried ground bark (1.5 kg) of Mesua elegans (Clusiaceae), collected from Sungai Badak Forest Reserve, Sintok, Kedah, Malaysia, was extracted with hexane (3 × 4 L, 48 h) at room temperature. The hexane was evaporated to give a yellow gum (120 g). A portion of the extract (10 g) was subjected to column chromatography over silica gel (230–400 mesh) and eluted with hexane:ethyl acetate (from 9.5 to 0) and ethyl acetate:methanol (5:5) to give six fractions. The first fraction was subjected to further silica gel chromatography and eluted with hexane:ethyl acetate (from 9.7 to 9.4) to produce two other sub-fractions. The co-crystal was obtained from the second sub-fraction and recrystallized from its methanol solution as colourless prisms.

Structure description top

In the crystal, the lactone-carbonyl atom participates in two C—H···O interactions, Table 1, to link molecules into a supramolecular chain along the a axis, Fig. 3.

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).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the first (2-methyl butanoyl) component of (I) showing displacement ellipsoids at the 50% probability level.
	Fig. 2. The molecular structure of the second (3-methyl butanoyl) component of (I) showing displacement ellipsoids at the 50% probability level.
	Fig. 3. A view in projection down the a axis of the unit-cell contents of (I). The C—H···O interactions are shown as orange dashed lines.

6-[(2E)-3,7-Dimethylocta-2,6-dien-1-yl]-5,7-dihydroxy-8-(2- methylbutanoyl)-4-phenyl-2H-chromen-2-one–6-[(2E)-3,7- dimethylocta-2,6-dien-1-yl]-5,7-dihydroxy-8-(3-methylbutanoyl)-4-phenyl- 2H-chromen-2-one (1/1) top

Crystal data top

C₃₀H₃₄O₅·C₃₀H₃₄O₅	Z = 1
M_r = 949.14	F(000) = 508
Triclinic, P1	D_x = 1.231 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 5.9426 (2) Å	Cell parameters from 8956 reflections
b = 13.4688 (5) Å	θ = 2.8–76.3°
c = 16.3275 (6) Å	µ = 0.66 mm⁻¹
α = 91.955 (3)°	T = 100 K
β = 99.515 (3)°	Prism, colourless
γ = 95.834 (3)°	0.30 × 0.15 × 0.05 mm
V = 1280.47 (8) Å³

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	5330 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	4528 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.045
Detector resolution: 10.4041 pixels mm^-1	θ_max = 76.5°, θ_min = 2.8°
ω scan	h = −7→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −16→16
T_min = 0.826, T_max = 0.968	l = −20→20
25960 measured 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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.208	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.1357P)² + 0.5208P] where P = (F_o² + 2F_c²)/3
5330 reflections	(Δ/σ)_max = 0.001
363 parameters	Δρ_max = 0.57 e Å⁻³
54 restraints	Δρ_min = −0.53 e Å⁻³

Crystal data top

C₃₀H₃₄O₅·C₃₀H₃₄O₅	γ = 95.834 (3)°
M_r = 949.14	V = 1280.47 (8) Å³
Triclinic, P1	Z = 1
a = 5.9426 (2) Å	Cu Kα radiation
b = 13.4688 (5) Å	µ = 0.66 mm⁻¹
c = 16.3275 (6) Å	T = 100 K
α = 91.955 (3)°	0.30 × 0.15 × 0.05 mm
β = 99.515 (3)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	5330 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	4528 reflections with I > 2σ(I)
T_min = 0.826, T_max = 0.968	R_int = 0.045
25960 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	54 restraints
wR(F²) = 0.208	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.57 e Å⁻³
5330 reflections	Δρ_min = −0.53 e Å⁻³
363 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.9303 (2)	0.47777 (9)	0.36863 (8)	0.0331 (3)
O2	1.2727 (2)	0.55978 (10)	0.41312 (9)	0.0390 (3)
O3	0.7244 (2)	0.13093 (9)	0.41205 (9)	0.0399 (4)
H3o	0.851 (3)	0.138 (2)	0.4450 (14)	0.052 (7)*
O4	0.1977 (2)	0.30693 (11)	0.25255 (9)	0.0415 (4)
H4o	0.198 (6)	0.3641 (14)	0.232 (2)	0.080 (10)*
O5	0.284 (4)	0.473 (2)	0.218 (3)	0.046 (2)	0.50
O5'	0.308 (4)	0.489 (2)	0.223 (3)	0.046 (2)	0.50
C1	1.1476 (3)	0.48355 (13)	0.41647 (12)	0.0329 (4)
C2	1.1949 (3)	0.40121 (13)	0.46801 (11)	0.0325 (4)
H2	1.3363	0.4046	0.5055	0.039*
C3	1.0417 (3)	0.31880 (13)	0.46420 (11)	0.0311 (4)
C4	0.8304 (3)	0.30996 (13)	0.40438 (11)	0.0308 (4)
C5	0.6749 (3)	0.22155 (13)	0.38407 (11)	0.0326 (4)
C6	0.4647 (3)	0.22110 (13)	0.33394 (11)	0.0340 (4)
C7	0.4069 (3)	0.31019 (14)	0.29808 (11)	0.0344 (4)
C8	0.5641 (3)	0.39885 (14)	0.30749 (11)	0.0344 (4)
C9	0.7747 (3)	0.39437 (13)	0.36031 (11)	0.0314 (4)
C10	1.0886 (3)	0.24091 (13)	0.52593 (11)	0.0330 (4)
C11	1.2800 (4)	0.18927 (16)	0.52804 (13)	0.0422 (5)
H11	1.3861	0.2055	0.4917	0.051*
C12	1.3170 (4)	0.11372 (18)	0.58338 (15)	0.0508 (6)
H12	1.4461	0.0774	0.5836	0.061*
C13	1.1665 (4)	0.09147 (16)	0.63781 (14)	0.0475 (5)
H13	1.1912	0.0395	0.6751	0.057*
C14	0.9803 (4)	0.14473 (15)	0.63803 (13)	0.0439 (5)
H14	0.8794	0.1305	0.6766	0.053*
C15	0.9392 (4)	0.21920 (14)	0.58222 (13)	0.0390 (4)
H15	0.8098	0.2552	0.5824	0.047*
C16	0.3045 (3)	0.12556 (14)	0.31303 (12)	0.0372 (4)
H16A	0.3228	0.0817	0.3606	0.045*
H16B	0.1435	0.1414	0.3026	0.045*
C17	0.3576 (3)	0.07200 (14)	0.23678 (13)	0.0377 (4)
H17	0.5157	0.0679	0.2355	0.045*
C18	0.2122 (3)	0.03001 (13)	0.17137 (12)	0.0336 (4)
C19	−0.0431 (3)	0.02650 (17)	0.16256 (13)	0.0427 (5)
H19A	−0.0823	0.0682	0.2074	0.064*
H19B	−0.1095	−0.0426	0.1658	0.064*
H19C	−0.1049	0.0516	0.1087	0.064*
C20	0.2995 (3)	−0.01785 (14)	0.09938 (12)	0.0378 (4)
H20A	0.4624	0.0082	0.1015	0.045*
H20B	0.2117	0.0022	0.0468	0.045*
C21	0.2809 (5)	−0.13182 (16)	0.09853 (15)	0.0547 (6)
H21A	0.3737	−0.1526	0.1499	0.066*
H21B	0.1191	−0.1584	0.0979	0.066*
C22	0.3627 (5)	−0.17516 (16)	0.02434 (15)	0.0501 (5)
H22	0.5179	−0.1552	0.0197	0.060*
C23	0.2449 (4)	−0.23810 (17)	−0.03575 (14)	0.0501 (5)
C24	0.3472 (5)	−0.27142 (19)	−0.10876 (16)	0.0590 (6)
H24A	0.5074	−0.2421	−0.1023	0.089*
H24B	0.2603	−0.2494	−0.1600	0.089*
H24C	0.3409	−0.3445	−0.1116	0.089*
C25	0.0024 (6)	−0.2785 (4)	−0.0393 (2)	0.0989 (14)
H25A	−0.0533	−0.2536	0.0100	0.148*
H25B	−0.0096	−0.3517	−0.0407	0.148*
H25C	−0.0907	−0.2570	−0.0895	0.148*
C26	0.480 (2)	0.4832 (7)	0.2594 (10)	0.0424 (9)	0.50
C27	0.6207 (16)	0.5821 (7)	0.2569 (5)	0.0590 (13)	0.50
H27	0.7212	0.5942	0.3125	0.071*	0.50
C26'	0.506 (2)	0.4880 (7)	0.2608 (9)	0.0424 (9)	0.50
C27'	0.6741 (18)	0.5785 (8)	0.2554 (6)	0.0590 (13)	0.50
H27A	0.8304	0.5578	0.2586	0.071*	0.50
H27B	0.6755	0.6263	0.3029	0.071*	0.50
C28	0.7818 (6)	0.5736 (2)	0.1937 (2)	0.0311 (7)	0.50
H28A	0.8578	0.5118	0.2025	0.037*	0.50
H28B	0.6900	0.5676	0.1370	0.037*	0.50
C29	0.9641 (7)	0.6620 (3)	0.1995 (3)	0.0458 (9)	0.50
H29A	1.0600	0.6530	0.1570	0.069*	0.50
H29B	1.0598	0.6668	0.2547	0.069*	0.50
H29C	0.8902	0.7235	0.1905	0.069*	0.50
C30	0.4816 (13)	0.6723 (6)	0.2447 (5)	0.117 (3)	0.50
H30A	0.3892	0.6764	0.2889	0.176*	0.50
H30B	0.3803	0.6642	0.1905	0.176*	0.50
H30C	0.5868	0.7336	0.2469	0.176*	0.50
C28'	0.6076 (11)	0.6297 (4)	0.1732 (3)	0.0737 (16)	0.50
H28'	0.4480	0.6489	0.1690	0.088*	0.50
C29'	0.7783 (13)	0.7238 (4)	0.1787 (4)	0.089 (2)	0.50
H29D	0.7365	0.7635	0.1304	0.133*	0.50
H29E	0.9333	0.7046	0.1794	0.133*	0.50
H29F	0.7744	0.7635	0.2298	0.133*	0.50
C30'	0.6254 (7)	0.5651 (3)	0.0980 (2)	0.0362 (8)	0.50
H30D	0.5155	0.5051	0.0944	0.054*	0.50
H30E	0.7814	0.5457	0.1029	0.054*	0.50
H30F	0.5910	0.6025	0.0479	0.054*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0368 (7)	0.0244 (6)	0.0359 (7)	−0.0024 (5)	0.0040 (5)	−0.0023 (5)
O2	0.0393 (7)	0.0253 (6)	0.0494 (8)	−0.0036 (5)	0.0038 (6)	−0.0011 (5)
O3	0.0433 (8)	0.0231 (6)	0.0500 (8)	−0.0009 (5)	0.0025 (6)	−0.0037 (5)
O4	0.0383 (7)	0.0393 (8)	0.0431 (8)	−0.0025 (6)	0.0004 (6)	−0.0012 (6)
O5	0.049 (4)	0.029 (7)	0.051 (4)	−0.010 (4)	−0.012 (3)	0.001 (6)
O5'	0.049 (4)	0.029 (7)	0.051 (4)	−0.010 (4)	−0.012 (3)	0.001 (6)
C1	0.0351 (9)	0.0258 (8)	0.0366 (9)	−0.0003 (7)	0.0062 (7)	−0.0049 (7)
C2	0.0335 (9)	0.0274 (9)	0.0351 (9)	−0.0004 (7)	0.0045 (7)	−0.0024 (7)
C3	0.0353 (9)	0.0255 (8)	0.0329 (9)	0.0016 (7)	0.0089 (7)	−0.0044 (6)
C4	0.0338 (9)	0.0259 (8)	0.0323 (8)	−0.0013 (7)	0.0084 (7)	−0.0039 (6)
C5	0.0381 (9)	0.0248 (8)	0.0351 (9)	0.0001 (7)	0.0098 (7)	−0.0042 (7)
C6	0.0366 (9)	0.0285 (9)	0.0359 (9)	−0.0041 (7)	0.0089 (7)	−0.0066 (7)
C7	0.0364 (9)	0.0337 (9)	0.0317 (9)	−0.0013 (7)	0.0061 (7)	−0.0055 (7)
C8	0.0406 (10)	0.0302 (9)	0.0306 (8)	−0.0019 (7)	0.0056 (7)	−0.0032 (7)
C9	0.0355 (9)	0.0263 (8)	0.0315 (8)	−0.0027 (7)	0.0083 (7)	−0.0054 (6)
C10	0.0386 (9)	0.0248 (8)	0.0338 (9)	−0.0015 (7)	0.0052 (7)	−0.0029 (7)
C11	0.0449 (11)	0.0420 (11)	0.0431 (11)	0.0092 (9)	0.0131 (9)	0.0075 (8)
C12	0.0566 (13)	0.0470 (12)	0.0535 (13)	0.0172 (10)	0.0144 (10)	0.0115 (10)
C13	0.0650 (14)	0.0336 (10)	0.0455 (11)	0.0064 (9)	0.0128 (10)	0.0069 (8)
C14	0.0588 (13)	0.0320 (10)	0.0441 (11)	0.0018 (9)	0.0198 (9)	0.0035 (8)
C15	0.0453 (11)	0.0293 (9)	0.0441 (10)	0.0029 (8)	0.0137 (8)	−0.0001 (7)
C16	0.0371 (9)	0.0306 (9)	0.0415 (10)	−0.0047 (7)	0.0067 (8)	−0.0072 (7)
C17	0.0322 (9)	0.0322 (9)	0.0470 (11)	0.0008 (7)	0.0055 (8)	−0.0077 (8)
C18	0.0356 (9)	0.0264 (8)	0.0379 (9)	−0.0008 (7)	0.0060 (7)	−0.0002 (7)
C19	0.0368 (10)	0.0494 (12)	0.0400 (10)	−0.0012 (8)	0.0056 (8)	−0.0044 (8)
C20	0.0386 (10)	0.0322 (9)	0.0409 (10)	−0.0008 (7)	0.0064 (8)	−0.0050 (7)
C21	0.0848 (18)	0.0338 (11)	0.0472 (12)	0.0082 (11)	0.0157 (12)	−0.0017 (9)
C22	0.0640 (14)	0.0358 (11)	0.0521 (13)	0.0076 (10)	0.0146 (11)	−0.0051 (9)
C23	0.0633 (14)	0.0430 (11)	0.0439 (11)	0.0074 (10)	0.0083 (10)	−0.0009 (9)
C24	0.0779 (17)	0.0476 (13)	0.0526 (13)	0.0122 (12)	0.0136 (12)	−0.0113 (10)
C25	0.084 (2)	0.146 (4)	0.0572 (17)	−0.037 (2)	0.0231 (16)	−0.030 (2)
C26	0.048 (3)	0.0361 (12)	0.0364 (11)	−0.0067 (14)	−0.0059 (15)	0.0013 (10)
C27	0.051 (4)	0.0474 (15)	0.0629 (16)	−0.020 (2)	−0.0257 (19)	0.0194 (12)
C26'	0.048 (3)	0.0361 (12)	0.0364 (11)	−0.0067 (14)	−0.0059 (15)	0.0013 (10)
C27'	0.051 (4)	0.0474 (15)	0.0629 (16)	−0.020 (2)	−0.0257 (19)	0.0194 (12)
C28	0.0366 (17)	0.0258 (16)	0.0301 (16)	0.0024 (13)	0.0019 (13)	0.0110 (12)
C29	0.050 (2)	0.0336 (19)	0.054 (2)	−0.0012 (17)	0.0135 (19)	0.0053 (17)
C30	0.115 (6)	0.101 (5)	0.114 (6)	−0.012 (5)	−0.033 (5)	0.032 (5)
C28'	0.078 (4)	0.064 (3)	0.073 (4)	−0.001 (3)	−0.001 (3)	0.005 (3)
C29'	0.101 (5)	0.068 (4)	0.089 (4)	−0.005 (3)	−0.004 (4)	0.017 (3)
C30'	0.051 (2)	0.0264 (16)	0.0316 (17)	−0.0002 (15)	0.0093 (15)	0.0057 (13)

Geometric parameters (Å, º) top

O1—C9	1.368 (2)	C19—H19C	0.9800
O1—C1	1.388 (2)	C20—C21	1.527 (3)
O2—C1	1.213 (2)	C20—H20A	0.9900
O3—C5	1.361 (2)	C20—H20B	0.9900
O3—H3o	0.844 (10)	C21—C22	1.499 (3)
O4—C7	1.335 (2)	C21—H21A	0.9900
O4—H4o	0.853 (10)	C21—H21B	0.9900
O5—C26	1.240 (6)	C22—C23	1.329 (3)
O5'—C26'	1.238 (6)	C22—H22	0.9500
C1—C2	1.437 (3)	C23—C25	1.479 (4)
C2—C3	1.355 (2)	C23—C24	1.500 (3)
C2—H2	0.9500	C24—H24A	0.9800
C3—C4	1.450 (3)	C24—H24B	0.9800
C3—C10	1.494 (2)	C24—H24C	0.9800
C4—C9	1.405 (3)	C25—H25A	0.9800
C4—C5	1.425 (2)	C25—H25B	0.9800
C5—C6	1.375 (3)	C25—H25C	0.9800
C6—C7	1.402 (3)	C26—C27	1.504 (6)
C6—C16	1.514 (2)	C27—C28	1.528 (4)
C7—C8	1.427 (3)	C27—C30	1.538 (5)
C8—C9	1.405 (3)	C27—H27	1.0000
C8—C26	1.483 (6)	C26'—C27'	1.510 (6)
C8—C26'	1.484 (6)	C27'—C28'	1.541 (11)
C10—C11	1.389 (3)	C27'—H27A	0.9900
C10—C15	1.398 (3)	C27'—H27B	0.9900
C11—C12	1.394 (3)	C28—C29	1.516 (4)
C11—H11	0.9500	C28—H28A	0.9900
C12—C13	1.380 (3)	C28—H28B	0.9900
C12—H12	0.9500	C29—H29A	0.9800
C13—C14	1.379 (3)	C29—H29B	0.9800
C13—H13	0.9500	C29—H29C	0.9800
C14—C15	1.391 (3)	C30—H30A	0.9800
C14—H14	0.9500	C30—H30B	0.9800
C15—H15	0.9500	C30—H30C	0.9800
C16—C17	1.511 (3)	C28'—C30'	1.505 (4)
C16—H16A	0.9900	C28'—C29'	1.531 (4)
C16—H16B	0.9900	C28'—H28'	1.0000
C17—C18	1.327 (3)	C29'—H29D	0.9800
C17—H17	0.9500	C29'—H29E	0.9800
C18—C19	1.496 (3)	C29'—H29F	0.9800
C18—C20	1.511 (3)	C30'—H30D	0.9800
C19—H19A	0.9800	C30'—H30E	0.9800
C19—H19B	0.9800	C30'—H30F	0.9800

C9—O1—C1	123.73 (14)	C20—C21—H21A	109.3
C5—O3—H3o	108.8 (19)	C22—C21—H21B	109.3
C7—O4—H4o	103 (2)	C20—C21—H21B	109.3
O2—C1—O1	116.26 (17)	H21A—C21—H21B	108.0
O2—C1—C2	127.17 (18)	C23—C22—C21	128.0 (2)
O1—C1—C2	116.46 (15)	C23—C22—H22	116.0
C3—C2—C1	121.27 (17)	C21—C22—H22	116.0
C3—C2—H2	119.4	C22—C23—C25	124.1 (2)
C1—C2—H2	119.4	C22—C23—C24	122.0 (2)
C2—C3—C4	120.15 (17)	C25—C23—C24	113.8 (2)
C2—C3—C10	118.72 (17)	C23—C24—H24A	109.5
C4—C3—C10	121.03 (15)	C23—C24—H24B	109.5
C9—C4—C5	116.29 (17)	H24A—C24—H24B	109.5
C9—C4—C3	118.02 (16)	C23—C24—H24C	109.5
C5—C4—C3	125.66 (17)	H24A—C24—H24C	109.5
O3—C5—C6	114.94 (16)	H24B—C24—H24C	109.5
O3—C5—C4	122.49 (17)	C23—C25—H25A	109.5
C6—C5—C4	122.57 (17)	C23—C25—H25B	109.5
C5—C6—C7	118.48 (16)	H25A—C25—H25B	109.5
C5—C6—C16	121.17 (17)	C23—C25—H25C	109.5
C7—C6—C16	120.24 (17)	H25A—C25—H25C	109.5
O4—C7—C6	116.21 (16)	H25B—C25—H25C	109.5
O4—C7—C8	121.54 (17)	O5—C26—C8	119.2 (19)
C6—C7—C8	122.22 (17)	O5—C26—C27	116.9 (16)
C9—C8—C7	116.14 (17)	C8—C26—C27	123.9 (8)
C9—C8—C26	129.2 (6)	C26—C27—C28	109.4 (9)
C7—C8—C26	114.7 (6)	C26—C27—C30	115.0 (7)
C9—C8—C26'	123.4 (6)	C28—C27—C30	113.0 (5)
C7—C8—C26'	120.5 (6)	C26—C27—H27	106.2
O1—C9—C8	117.12 (16)	C28—C27—H27	106.2
O1—C9—C4	119.40 (16)	C30—C27—H27	106.2
C8—C9—C4	123.48 (16)	O5'—C26'—C8	118.4 (19)
C11—C10—C15	119.28 (18)	O5'—C26'—C27'	117.3 (17)
C11—C10—C3	120.61 (17)	C8—C26'—C27'	124.3 (9)
C15—C10—C3	120.11 (17)	C26'—C27'—C28'	110.6 (7)
C10—C11—C12	120.20 (19)	C26'—C27'—H27A	109.5
C10—C11—H11	119.9	C28'—C27'—H27A	109.5
C12—C11—H11	119.9	C26'—C27'—H27B	109.5
C13—C12—C11	120.2 (2)	C28'—C27'—H27B	109.5
C13—C12—H12	119.9	H27A—C27'—H27B	108.1
C11—C12—H12	119.9	C29—C28—C27	113.2 (5)
C14—C13—C12	120.0 (2)	C29—C28—H28A	108.9
C14—C13—H13	120.0	C27—C28—H28A	108.9
C12—C13—H13	120.0	C29—C28—H28B	108.9
C13—C14—C15	120.48 (19)	C27—C28—H28B	108.9
C13—C14—H14	119.8	H28A—C28—H28B	107.8
C15—C14—H14	119.8	C28—C29—H29A	109.5
C14—C15—C10	119.84 (19)	C28—C29—H29B	109.5
C14—C15—H15	120.1	H29A—C29—H29B	109.5
C10—C15—H15	120.1	C28—C29—H29C	109.5
C17—C16—C6	110.01 (16)	H29A—C29—H29C	109.5
C17—C16—H16A	109.7	H29B—C29—H29C	109.5
C6—C16—H16A	109.7	C27—C30—H30A	109.5
C17—C16—H16B	109.7	C27—C30—H30B	109.5
C6—C16—H16B	109.7	H30A—C30—H30B	109.5
H16A—C16—H16B	108.2	C27—C30—H30C	109.5
C18—C17—C16	128.44 (18)	H30A—C30—H30C	109.5
C18—C17—H17	115.8	H30B—C30—H30C	109.5
C16—C17—H17	115.8	C30'—C28'—C29'	109.5 (4)
C17—C18—C19	123.89 (18)	C30'—C28'—C27'	112.7 (6)
C17—C18—C20	120.64 (18)	C29'—C28'—C27'	105.2 (7)
C19—C18—C20	115.46 (16)	C30'—C28'—H28'	109.8
C18—C19—H19A	109.5	C29'—C28'—H28'	109.8
C18—C19—H19B	109.5	C27'—C28'—H28'	109.8
H19A—C19—H19B	109.5	C28'—C29'—H29D	109.5
C18—C19—H19C	109.5	C28'—C29'—H29E	109.5
H19A—C19—H19C	109.5	H29D—C29'—H29E	109.5
H19B—C19—H19C	109.5	C28'—C29'—H29F	109.5
C18—C20—C21	114.04 (17)	H29D—C29'—H29F	109.5
C18—C20—H20A	108.7	H29E—C29'—H29F	109.5
C21—C20—H20A	108.7	C28'—C30'—H30D	109.5
C18—C20—H20B	108.7	C28'—C30'—H30E	109.5
C21—C20—H20B	108.7	H30D—C30'—H30E	109.5
H20A—C20—H20B	107.6	C28'—C30'—H30F	109.5
C22—C21—C20	111.63 (19)	H30D—C30'—H30F	109.5
C22—C21—H21A	109.3	H30E—C30'—H30F	109.5

C9—O1—C1—O2	174.82 (16)	C4—C3—C10—C15	−59.2 (2)
C9—O1—C1—C2	−8.6 (2)	C15—C10—C11—C12	2.7 (3)
O2—C1—C2—C3	−178.28 (18)	C3—C10—C11—C12	−177.2 (2)
O1—C1—C2—C3	5.6 (3)	C10—C11—C12—C13	−1.6 (4)
C1—C2—C3—C4	3.2 (3)	C11—C12—C13—C14	−0.6 (4)
C1—C2—C3—C10	−173.11 (16)	C12—C13—C14—C15	1.7 (3)
C2—C3—C4—C9	−9.5 (3)	C13—C14—C15—C10	−0.6 (3)
C10—C3—C4—C9	166.80 (16)	C11—C10—C15—C14	−1.6 (3)
C2—C3—C4—C5	168.59 (17)	C3—C10—C15—C14	178.26 (18)
C10—C3—C4—C5	−15.1 (3)	C5—C6—C16—C17	−87.8 (2)
C9—C4—C5—O3	169.56 (16)	C7—C6—C16—C17	88.2 (2)
C3—C4—C5—O3	−8.5 (3)	C6—C16—C17—C18	−135.2 (2)
C9—C4—C5—C6	−9.6 (3)	C16—C17—C18—C19	−1.5 (3)
C3—C4—C5—C6	172.29 (17)	C16—C17—C18—C20	178.18 (18)
O3—C5—C6—C7	−175.86 (16)	C17—C18—C20—C21	102.3 (2)
C4—C5—C6—C7	3.4 (3)	C19—C18—C20—C21	−78.0 (2)
O3—C5—C6—C16	0.2 (3)	C18—C20—C21—C22	178.11 (19)
C4—C5—C6—C16	179.46 (16)	C20—C21—C22—C23	−119.9 (3)
C5—C6—C7—O4	−177.50 (16)	C21—C22—C23—C25	−0.6 (5)
C16—C6—C7—O4	6.4 (3)	C21—C22—C23—C24	177.0 (2)
C5—C6—C7—C8	4.2 (3)	C9—C8—C26—O5	−177.9 (19)
C16—C6—C7—C8	−171.91 (17)	C7—C8—C26—O5	2.2 (10)
O4—C7—C8—C9	176.91 (16)	C26'—C8—C26—O5	165 (12)
C6—C7—C8—C9	−4.9 (3)	C9—C8—C26—C27	2.8 (19)
O4—C7—C8—C26	−3.1 (8)	C7—C8—C26—C27	−177.2 (10)
C6—C7—C8—C26	175.1 (8)	C26'—C8—C26—C27	−14 (12)
O4—C7—C8—C26'	−5.2 (8)	O5—C26—C27—C28	−97.7 (14)
C6—C7—C8—C26'	173.0 (8)	C8—C26—C27—C28	81.7 (14)
C1—O1—C9—C8	−177.96 (15)	O5—C26—C27—C30	30.8 (11)
C1—O1—C9—C4	2.4 (2)	C8—C26—C27—C30	−149.8 (11)
C7—C8—C9—O1	178.44 (15)	C9—C8—C26'—O5'	−172.3 (17)
C26—C8—C9—O1	−1.5 (9)	C7—C8—C26'—O5'	9.9 (9)
C26'—C8—C9—O1	0.6 (9)	C26—C8—C26'—O5'	−8 (14)
C7—C8—C9—C4	−2.0 (3)	C9—C8—C26'—C27'	8.4 (18)
C26—C8—C9—C4	178.1 (9)	C7—C8—C26'—C27'	−169.4 (9)
C26'—C8—C9—C4	−179.8 (8)	C26—C8—C26'—C27'	173 (14)
C5—C4—C9—O1	−171.55 (15)	O5'—C26'—C27'—C28'	−27.9 (12)
C3—C4—C9—O1	6.7 (2)	C8—C26'—C27'—C28'	151.4 (12)
C5—C4—C9—C8	8.9 (3)	C26—C27—C28—C29	−167.9 (5)
C3—C4—C9—C8	−172.90 (16)	C30—C27—C28—C29	62.5 (9)
C2—C3—C10—C11	−63.0 (2)	C26'—C27'—C28'—C30'	−65.2 (9)
C4—C3—C10—C11	120.7 (2)	C26'—C27'—C28'—C29'	175.6 (8)
C2—C3—C10—C15	117.1 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C10–C15 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4o···O5	0.85 (1)	1.54 (4)	2.35 (3)	158 (4)
O4—H4o···O5′	0.85 (1)	1.76 (4)	2.55 (3)	154 (3)
O3—H3o···Cg1	0.84 (2)	2.56 (4)	3.355 (2)	158 (4)
C2—H2···O2ⁱ	0.95	2.47	3.408 (2)	169
C15—H15···O2ⁱⁱ	0.95	2.59	3.351 (2)	137

Symmetry codes: (i) −x+3, −y+1, −z+1; (ii) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₃₀H₃₄O₅·C₃₀H₃₄O₅
M_r	949.14
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	5.9426 (2), 13.4688 (5), 16.3275 (6)
α, β, γ (°)	91.955 (3), 99.515 (3), 95.834 (3)
V (Å³)	1280.47 (8)
Z	1
Radiation type	Cu Kα
µ (mm⁻¹)	0.66
Crystal size (mm)	0.30 × 0.15 × 0.05

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.826, 0.968
No. of measured, independent and observed [I > 2σ(I)] reflections	25960, 5330, 4528
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.631

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.208, 1.01
No. of reflections	5330
No. of parameters	363
No. of restraints	54
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.53

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C10–C15 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4o···O5	0.85 (1)	1.54 (4)	2.35 (3)	158 (4)
O4—H4o···O5'	0.85 (1)	1.76 (4)	2.55 (3)	154 (3)
O3—H3o···Cg1	0.84 (2)	2.56 (4)	3.355 (2)	158 (4)
C2—H2···O2ⁱ	0.95	2.47	3.408 (2)	169
C15—H15···O2ⁱⁱ	0.95	2.59	3.351 (2)	137

Symmetry codes: (i) −x+3, −y+1, −z+1; (ii) −x+2, −y+1, −z+1.

Footnotes

¹Additional correspondence author, e-mail: khalijah@um.edu.my.

Acknowledgements

The authors thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12), 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.

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Awang, K., Chan, G., Litaudon, M., Ismail, N. H., Martin, M.-T. & Gueritte, F. (2010). Bioorg. Med. Chem. 18, 7873–7877. Web of Science CrossRef CAS PubMed Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Verotta, L., Lovaglio, E., Vidari, G., Finzi, P. V., Neri, M. G., Raimondi, A., Parapini, S., Taramelli, D., Riva, A. & Bombardelli, E. (2004). Phytochemistry, 65, 2867–2879. Web of Science CrossRef PubMed CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 4| April 2012| Pages o939-o940

doi:10.1107/S1600536812008628

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

6-[(2E)-3,7-Di­methyl­octa-2,6-dien-1-yl]-5,7-dihy­dr­oxy-8-(2-methyl­butano­yl)-4-phenyl-2H-chromen-2-one–6-[(2E)-3,7-di­methyl­octa-2,6-dien-1-yl]-5,7-dihy­dr­oxy-8-(3-methyl­butano­yl)-4-phenyl-2H-chromen-2-one (1/1) from Mesua elegans1

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

6-[(2E)-3,7-Dimethylocta-2,6-dien-1-yl]-5,7-dihydroxy-8-(2-methylbutanoyl)-4-phenyl-2H-chromen-2-one–6-[(2E)-3,7-dimethylocta-2,6-dien-1-yl]-5,7-dihydroxy-8-(3-methylbutanoyl)-4-phenyl-2H-chromen-2-one (1/1) from Mesua elegans¹