Whole-mol­ecule disordered (E)-2-(1-hy­droxy-3-phenylprop-2-en-1-yl­idene)-4,5-dimeth­oxycyclo­pent-4-ene-1,3-dione isolated from Lindera oxyphylla (Lauraceae)

Hosseinzadeh, M.; Mukhtar, M.R.; Mohamad, J.; Awang, K.; Ng, S.W.

doi:10.1107/S1600536811019386

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1544

doi:10.1107/S1600536811019386

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Whole-molecule disordered (E)-2-(1-hydroxy-3-phenylprop-2-en-1-ylidene)-4,5-dimethoxycyclopent-4-ene-1,3-dione isolated from Lindera oxyphylla (Lauraceae)

Masoumeh Hosseinzadeh,^a Mat Ropi Mukhtar,^a Jamaludin Mohamad,^b Khalijah Awang ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^bInstitute of Biological Sciences, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 21 May 2011; accepted 23 May 2011; online 28 May 2011)

In the molecule of the title compound, C₁₆H₁₄O₅, all non-H atoms are approximately co-planar [maximum atomic deviation = 0.064 (5) Å]. The hydroxy group is a hydrogen-bond donor to a carbonyl O atom. Weak intermolecular C—H⋯O hydrogen bonding is present in the crystal structure. The crystal structure is 'whole-molecule disordered' about an axis that runs approximately along the length of the molecule; the occupancy of the two disorder components was set as exactly 0.5. An intramolecular O—-H⋯O hydrogen bond exists in each component.

Related literature

For the spectroscopic characterization of linderone and methyl linderone isolated from Lindera pipericarpa, see: Kiang et al. (1962 ). For the crystal structure of methyl linderone isolated from Lindera poliantha, see: Syah et al. (2005 ).

Experimental

Crystal data

C₁₆H₁₄O₅
M_r = 286.27
Monoclinic, P 2₁ /n
a = 7.3195 (5) Å
b = 9.8635 (7) Å
c = 18.6724 (11) Å
β = 96.586 (6)°
V = 1339.17 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 100 K
0.20 × 0.20 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.979, T_max = 0.990
8436 measured reflections
2369 independent reflections
1965 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.068
wR(F²) = 0.190
S = 1.05
2369 reflections
308 parameters
30 restraints
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.84	1.93	2.600 (5)	136
O1′—H1′⋯O2′	0.84	1.97	2.623 (4)	134
C2—H2⋯O2ⁱ	0.95	2.26	3.091 (8)	145
C16′—H16D⋯O1′ⁱⁱ	0.98	2.05	2.885 (11)	142
Symmetry codes: (i) x, y+1, z; (ii) x, y-1, z.

Data collection: CrysAlis PRO (Agilent, 2010); 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: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811019386/xu5217sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811019386/xu5217Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811019386/xu5217Isup3.cml

checkCIF report

Comment top

Linderone (Scheme I) was isolated from Lindera pipericarpa and its formulation was established by solution 1H-NMR spectrocopy (Kiang et al., 1962) nearly 50 years ago. This plant genus also yields methyl linderone, which differs from linderone in having a methyl group in place of the hydroxy H atom. Methyl linderone, isolated from Lindera poliantha, exists as a planar molecule (Syah et al., 2005). Linderone is similarly a planar molecule; however, the molecule is 'whole-molecule' disordered (Fig. 1) about an axis that runs approximately along the length of the flat molecule. The three-atom chain connecting the five-membered and six-membered rings exists in an E-configuration; the hydroxy group is hydrogen-bond donor to the carbonyl O atom.

Related literature top

For the spectroscopic characterization of linderone and methyl linderone isolated from Lindera pipericarpa, see: Kiang et al. (1962). For the crystal structure of methyl linderone isolated from Lindera poliantha, see: Syah et al. (2005).

Experimental top

Lindera oxyphylla (Lauraceae) was collected from Ulu Muda, Baling, Kedah, Malaysia. Some 4 kg of dried and ground bark of Lindera oxyphylla were extracted with hexane (10 L) for 3 days. The hexane extract was concentrated under reduced pressure to give a crude material (13 g). This was subjected to column chromatography on silica gel-60 (2 x 75 cm, 70–230 mesh ASTM) by using a step gradient of hexane and dichloromethane. The separation afforded 30 fractions; fractions 22–30 were purified by using dichloromethane–methanol (98:2) to yield (E)- 2-(1-hydroxy-3-phenyl-2-propen-1-ylidene)-4,5-dimethoxy-4-cyclopentene-1,3-dione. Its formulation was established by solution NMR spectroscopic analysis. Deep yellow prisms were obtained upon recrystallization from dichloromethane.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of one of the whole-molcule disordered components of C₁₆H₁₄O₅ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

(E)-2-(1-hydroxy-3-phenylprop-2-en-1-ylidene)-4,5-dimethoxycyclopent- 4-ene-1,3-dione top

Crystal data top

C₁₆H₁₄O₅	F(000) = 600
M_r = 286.27	D_x = 1.420 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4706 reflections
a = 7.3195 (5) Å	θ = 2.2–25.0°
b = 9.8635 (7) Å	µ = 0.11 mm⁻¹
c = 18.6724 (11) Å	T = 100 K
β = 96.586 (6)°	Prism, yellow
V = 1339.17 (15) Å³	0.20 × 0.20 × 0.10 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2369 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1965 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.032
Detector resolution: 10.4041 pixels mm^-1	θ_max = 25.1°, θ_min = 2.2°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −11→10
T_min = 0.979, T_max = 0.990	l = −22→22
8436 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.068	H-atom parameters constrained
wR(F²) = 0.190	w = 1/[σ²(F_o²) + (0.0883P)² + 1.2962P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
2369 reflections	Δρ_max = 0.56 e Å⁻³
308 parameters	Δρ_min = −0.34 e Å⁻³
30 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0014 (11)

Crystal data top

C₁₆H₁₄O₅	V = 1339.17 (15) Å³
M_r = 286.27	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.3195 (5) Å	µ = 0.11 mm⁻¹
b = 9.8635 (7) Å	T = 100 K
c = 18.6724 (11) Å	0.20 × 0.20 × 0.10 mm
β = 96.586 (6)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	2369 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	1965 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.990	R_int = 0.032
8436 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	30 restraints
wR(F²) = 0.190	H-atom parameters constrained
S = 1.05	Δρ_max = 0.56 e Å⁻³
2369 reflections	Δρ_min = −0.34 e Å⁻³
308 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.1902 (5)	0.2729 (4)	0.58692 (19)	0.0387 (8)	0.50
H1	0.1994	0.1894	0.5793	0.058*	0.50
O2	0.2649 (5)	0.0774 (4)	0.50156 (19)	0.0417 (9)	0.50
O3	0.3802 (5)	0.0354 (4)	0.3530 (2)	0.0405 (9)	0.50
O4	0.4003 (4)	0.3167 (3)	0.29148 (16)	0.0326 (8)	0.50
O5	0.3180 (4)	0.5067 (4)	0.39499 (17)	0.0341 (8)	0.50
C1	0.1608 (5)	0.7931 (7)	0.6029 (2)	0.0322 (14)	0.50
H1a	0.1943	0.7828	0.5555	0.039*	0.50
C2	0.1349 (12)	0.9219 (5)	0.6302 (4)	0.038 (2)	0.50
H2	0.1507	0.9996	0.6015	0.046*	0.50
C3	0.0859 (18)	0.9370 (5)	0.6995 (5)	0.031 (3)	0.50
H3	0.0682	1.0250	0.7182	0.037*	0.50
C4	0.0629 (17)	0.8233 (7)	0.7415 (3)	0.033 (3)	0.50
H4	0.0294	0.8336	0.7889	0.040*	0.50
C5	0.0888 (9)	0.6945 (6)	0.7142 (3)	0.0282 (16)	0.50
H5	0.0730	0.6168	0.7429	0.034*	0.50
C6	0.1377 (5)	0.6794 (5)	0.6449 (3)	0.0245 (16)	0.50
C7	0.1602 (6)	0.5419 (5)	0.6182 (2)	0.0302 (10)	0.50
H7	0.1380	0.4705	0.6503	0.036*	0.50
C8	0.2094 (11)	0.5036 (8)	0.5527 (4)	0.0241 (15)	0.50
H8	0.2331	0.5701	0.5182	0.029*	0.50
C9	0.2249 (6)	0.3619 (5)	0.5364 (2)	0.0284 (10)	0.50
C10	0.2768 (5)	0.3111 (4)	0.47099 (16)	0.0217 (10)	0.50
C11	0.2933 (6)	0.1698 (3)	0.45873 (17)	0.0324 (11)	0.50
C12	0.3440 (6)	0.1517 (3)	0.38819 (19)	0.0183 (11)	0.50
C13	0.3588 (5)	0.2819 (4)	0.35685 (14)	0.0219 (9)	0.50
C14	0.3172 (5)	0.3804 (2)	0.4080 (2)	0.0254 (8)	0.50
C15	0.3509 (17)	−0.0907 (11)	0.3878 (5)	0.051 (2)	0.50
H15A	0.3823	−0.1658	0.3571	0.077*	0.50
H15B	0.2215	−0.0980	0.3962	0.077*	0.50
H15C	0.4289	−0.0947	0.4341	0.077*	0.50
C16	0.4447 (17)	0.2108 (10)	0.2420 (6)	0.032 (2)	0.50
H16A	0.4725	0.2520	0.1968	0.049*	0.50
H16B	0.3396	0.1494	0.2323	0.049*	0.50
H16C	0.5519	0.1597	0.2637	0.049*	0.50
O1'	0.3120 (4)	0.6031 (3)	0.42276 (16)	0.0284 (7)	0.50
H1'	0.3434	0.5848	0.3820	0.043*	0.50
O2'	0.3866 (4)	0.4149 (3)	0.33121 (15)	0.0286 (7)	0.50
O3'	0.3939 (4)	0.1087 (4)	0.31727 (17)	0.0303 (7)	0.50
O4'	0.2841 (5)	0.0061 (3)	0.46004 (18)	0.0356 (8)	0.50
O5'	0.2174 (5)	0.2272 (3)	0.54512 (19)	0.0349 (8)	0.50
C1'	0.1246 (5)	0.6426 (4)	0.6802 (3)	0.0236 (11)	0.50
H1'a	0.1350	0.5471	0.6754	0.028*	0.50
C2'	0.0771 (10)	0.6978 (7)	0.7440 (3)	0.0290 (16)	0.50
H2'	0.0550	0.6401	0.7828	0.035*	0.50
C3'	0.0618 (17)	0.8376 (7)	0.7510 (4)	0.031 (2)	0.50
H3'	0.0293	0.8753	0.7946	0.037*	0.50
C4'	0.0942 (18)	0.9221 (4)	0.6942 (5)	0.036 (3)	0.50
H4'	0.0838	1.0175	0.6990	0.043*	0.50
C5'	0.1418 (11)	0.8668 (5)	0.6304 (3)	0.0274 (16)	0.50
H5'	0.1639	0.9246	0.5916	0.033*	0.50
C6'	0.1570 (5)	0.7271 (5)	0.6234 (2)	0.0202 (15)	0.50
C7'	0.2082 (5)	0.6752 (4)	0.5545 (2)	0.0220 (9)	0.50
H7'	0.2306	0.7410	0.5193	0.026*	0.50
C8'	0.2262 (12)	0.5464 (7)	0.5363 (5)	0.0237 (15)	0.50
H8'	0.2028	0.4789	0.5704	0.028*	0.50
C9'	0.2790 (5)	0.5022 (4)	0.4682 (2)	0.0219 (9)	0.50
C10'	0.2968 (5)	0.3663 (3)	0.4479 (2)	0.0217 (10)	0.50
C11'	0.3503 (5)	0.3338 (3)	0.37918 (18)	0.0324 (11)	0.50
C12'	0.3537 (6)	0.1904 (3)	0.37286 (15)	0.0183 (11)	0.50
C13'	0.3024 (6)	0.1342 (2)	0.43766 (18)	0.0219 (9)	0.50
C14'	0.2673 (5)	0.2429 (4)	0.48403 (13)	0.0254 (8)	0.50
C15'	0.4107 (15)	0.1709 (10)	0.2489 (7)	0.034 (2)	0.50
H15D	0.4407	0.1017	0.2145	0.051*	0.50
H15E	0.5088	0.2391	0.2546	0.051*	0.50
H15F	0.2942	0.2146	0.2309	0.051*	0.50
C16'	0.3136 (18)	−0.1051 (11)	0.4120 (5)	0.054 (3)	0.50
H16D	0.2954	−0.1914	0.4362	0.081*	0.50
H16E	0.4394	−0.1009	0.3989	0.081*	0.50
H16F	0.2260	−0.0983	0.3683	0.081*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.053 (2)	0.035 (2)	0.0288 (19)	0.0007 (16)	0.0099 (16)	0.0090 (16)
O2	0.061 (2)	0.034 (2)	0.0326 (18)	0.0009 (17)	0.0146 (16)	0.0108 (17)
O3	0.056 (2)	0.0259 (19)	0.042 (2)	0.0032 (16)	0.0153 (17)	−0.0052 (17)
O4	0.0370 (18)	0.0352 (19)	0.0273 (16)	0.0001 (14)	0.0109 (13)	0.0018 (15)
O5	0.0366 (18)	0.037 (2)	0.0295 (17)	0.0010 (15)	0.0076 (14)	0.0037 (16)
C1	0.025 (3)	0.051 (5)	0.021 (3)	−0.001 (3)	0.005 (2)	−0.001 (3)
C2	0.031 (3)	0.041 (5)	0.043 (4)	−0.003 (4)	0.006 (3)	−0.006 (4)
C3	0.030 (5)	0.037 (4)	0.026 (5)	0.002 (4)	0.006 (4)	−0.009 (4)
C4	0.021 (5)	0.049 (7)	0.029 (3)	−0.005 (4)	0.004 (3)	−0.010 (4)
C5	0.028 (3)	0.032 (3)	0.025 (4)	0.000 (2)	0.006 (3)	−0.008 (4)
C6	0.020 (2)	0.028 (4)	0.027 (4)	−0.004 (2)	0.007 (2)	0.002 (3)
C7	0.026 (2)	0.038 (3)	0.026 (2)	−0.0021 (19)	0.0014 (17)	0.000 (2)
C8	0.023 (3)	0.032 (4)	0.018 (3)	0.001 (3)	0.004 (2)	0.001 (3)
C9	0.025 (2)	0.039 (3)	0.022 (2)	0.0005 (19)	0.0043 (17)	0.0036 (19)
C10	0.0244 (15)	0.022 (2)	0.019 (2)	0.0003 (17)	0.0042 (14)	0.0059 (18)
C11	0.034 (2)	0.033 (2)	0.030 (2)	0.0013 (18)	0.0023 (17)	−0.0119 (19)
C12	0.0202 (12)	0.015 (2)	0.0199 (18)	−0.0023 (15)	0.0056 (12)	0.0068 (19)
C13	0.0227 (16)	0.0248 (19)	0.0181 (17)	−0.0019 (14)	0.0022 (14)	0.0051 (16)
C14	0.0220 (16)	0.0245 (19)	0.029 (2)	−0.0042 (14)	−0.0012 (14)	0.0090 (17)
C15	0.077 (5)	0.023 (4)	0.057 (7)	0.008 (3)	0.024 (5)	0.006 (4)
C16	0.049 (5)	0.034 (5)	0.017 (3)	−0.011 (3)	0.011 (3)	−0.012 (3)
O1'	0.0424 (18)	0.0215 (17)	0.0233 (15)	−0.0008 (13)	0.0116 (13)	−0.0016 (13)
O2'	0.0358 (17)	0.0301 (18)	0.0210 (15)	−0.0019 (13)	0.0086 (12)	−0.0009 (13)
O3'	0.0394 (18)	0.0311 (18)	0.0220 (16)	0.0042 (14)	0.0098 (13)	−0.0035 (15)
O4'	0.055 (2)	0.0233 (17)	0.0293 (17)	0.0025 (15)	0.0097 (15)	−0.0069 (15)
O5'	0.058 (2)	0.0294 (19)	0.0205 (17)	−0.0003 (15)	0.0178 (16)	−0.0020 (15)
C1'	0.029 (2)	0.021 (3)	0.023 (3)	−0.003 (2)	0.011 (2)	0.003 (3)
C2'	0.030 (3)	0.035 (4)	0.024 (4)	−0.001 (2)	0.009 (3)	−0.009 (3)
C3'	0.028 (5)	0.028 (5)	0.036 (4)	−0.002 (3)	0.002 (3)	−0.012 (4)
C4'	0.026 (5)	0.026 (4)	0.055 (8)	−0.001 (3)	0.002 (5)	−0.013 (4)
C5'	0.028 (3)	0.029 (5)	0.025 (3)	0.000 (3)	0.005 (2)	−0.004 (3)
C6'	0.020 (2)	0.023 (4)	0.018 (3)	−0.002 (2)	0.003 (2)	0.006 (3)
C7'	0.020 (2)	0.025 (2)	0.021 (2)	−0.0014 (16)	0.0053 (16)	0.0032 (17)
C8'	0.027 (3)	0.018 (4)	0.026 (4)	0.001 (3)	0.003 (2)	0.007 (2)
C9'	0.0173 (19)	0.025 (2)	0.023 (2)	−0.0011 (16)	0.0002 (16)	0.0006 (17)
C10'	0.0244 (15)	0.022 (2)	0.019 (2)	0.0003 (17)	0.0042 (14)	0.0059 (18)
C11'	0.034 (2)	0.033 (2)	0.030 (2)	0.0013 (18)	0.0023 (17)	−0.0119 (19)
C12'	0.0202 (12)	0.015 (2)	0.0199 (18)	−0.0023 (15)	0.0056 (12)	0.0068 (19)
C13'	0.0227 (16)	0.0248 (19)	0.0181 (17)	−0.0019 (14)	0.0022 (14)	0.0051 (16)
C14'	0.0220 (16)	0.0245 (19)	0.029 (2)	−0.0042 (14)	−0.0012 (14)	0.0090 (17)
C15'	0.025 (4)	0.042 (6)	0.035 (4)	0.000 (4)	0.011 (3)	−0.010 (4)
C16'	0.101 (8)	0.021 (4)	0.041 (6)	0.001 (4)	0.017 (4)	−0.011 (4)

Geometric parameters (Å, º) top

O1—C9	1.334 (6)	O1'—C9'	1.347 (5)
O1—H1	0.8400	O1'—H1'	0.8400
O2—C11	1.246 (4)	O2'—C11'	1.252 (4)
O3—C12	1.364 (4)	O3'—C12'	1.373 (4)
O3—C15	1.431 (10)	O3'—C15'	1.434 (11)
O4—C13	1.336 (4)	O4'—C13'	1.342 (4)
O4—C16	1.455 (11)	O4'—C16'	1.449 (10)
O5—C14	1.269 (4)	O5'—C14'	1.247 (4)
C1—C2	1.3900	C1'—C2'	1.3900
C1—C6	1.3900	C1'—C6'	1.3900
C1—H1A	0.9500	C1'—H1'A	0.9500
C2—C3	1.3900	C2'—C3'	1.3900
C2—H2	0.9500	C2'—H2'	0.9500
C3—C4	1.3900	C3'—C4'	1.3900
C3—H3	0.9500	C3'—H3'	0.9500
C4—C5	1.3900	C4'—C5'	1.3900
C4—H4	0.9500	C4'—H4'	0.9500
C5—C6	1.3900	C5'—C6'	1.3900
C5—H5	0.9500	C5'—H5'	0.9500
C6—C7	1.460 (6)	C6'—C7'	1.473 (5)
C7—C8	1.367 (10)	C7'—C8'	1.326 (10)
C7—H7	0.9500	C7'—H7'	0.9500
C8—C9	1.437 (10)	C8'—C9'	1.438 (10)
C8—H8	0.9500	C8'—H8'	0.9500
C9—C10	1.412 (5)	C9'—C10'	1.404 (5)
C10—C11	1.4200	C10'—C11'	1.4200
C10—C14	1.4200	C10'—C14'	1.4200
C11—C12	1.4200	C11'—C12'	1.4200
C12—C13	1.4200	C12'—C13'	1.4200
C13—C14	1.4200	C13'—C14'	1.4200
C15—H15A	0.9800	C15'—H15D	0.9800
C15—H15B	0.9800	C15'—H15E	0.9800
C15—H15C	0.9800	C15'—H15F	0.9800
C16—H16A	0.9800	C16'—H16D	0.9800
C16—H16B	0.9800	C16'—H16E	0.9800
C16—H16C	0.9800	C16'—H16F	0.9800

C9—O1—H1	120.0	C9'—O1'—H1'	120.0
C12—O3—C15	117.7 (5)	C12'—O3'—C15'	118.0 (5)
C13—O4—C16	119.1 (5)	C13'—O4'—C16'	119.5 (5)
C2—C1—C6	120.0	C2'—C1'—C6'	120.0
C2—C1—H1A	120.0	C2'—C1'—H1'A	120.0
C6—C1—H1A	120.0	C6'—C1'—H1'A	120.0
C1—C2—C3	120.0	C3'—C2'—C1'	120.0
C1—C2—H2	120.0	C3'—C2'—H2'	120.0
C3—C2—H2	120.0	C1'—C2'—H2'	120.0
C4—C3—C2	120.0	C2'—C3'—C4'	120.0
C4—C3—H3	120.0	C2'—C3'—H3'	120.0
C2—C3—H3	120.0	C4'—C3'—H3'	120.0
C5—C4—C3	120.0	C5'—C4'—C3'	120.0
C5—C4—H4	120.0	C5'—C4'—H4'	120.0
C3—C4—H4	120.0	C3'—C4'—H4'	120.0
C4—C5—C6	120.0	C4'—C5'—C6'	120.0
C4—C5—H5	120.0	C4'—C5'—H5'	120.0
C6—C5—H5	120.0	C6'—C5'—H5'	120.0
C5—C6—C1	120.0	C5'—C6'—C1'	120.0
C5—C6—C7	117.9 (5)	C5'—C6'—C7'	117.3 (4)
C1—C6—C7	122.1 (5)	C1'—C6'—C7'	122.7 (4)
C8—C7—C6	127.8 (5)	C8'—C7'—C6'	126.8 (5)
C8—C7—H7	116.1	C8'—C7'—H7'	116.6
C6—C7—H7	116.1	C6'—C7'—H7'	116.6
C7—C8—C9	119.6 (6)	C7'—C8'—C9'	124.1 (5)
C7—C8—H8	120.2	C7'—C8'—H8'	117.9
C9—C8—H8	120.2	C9'—C8'—H8'	117.9
O1—C9—C10	118.1 (4)	O1'—C9'—C10'	120.4 (4)
O1—C9—C8	117.6 (5)	O1'—C9'—C8'	114.8 (4)
C10—C9—C8	124.3 (5)	C10'—C9'—C8'	124.8 (4)
C9—C10—C11	121.6 (4)	C9'—C10'—C11'	120.2 (3)
C9—C10—C14	130.4 (4)	C9'—C10'—C14'	131.8 (3)
C11—C10—C14	108.0	C11'—C10'—C14'	108.0
O2—C11—C12	125.7 (4)	O2'—C11'—C12'	124.7 (3)
O2—C11—C10	126.2 (4)	O2'—C11'—C10'	127.3 (3)
C12—C11—C10	108.0	C12'—C11'—C10'	108.0
O3—C12—C13	122.3 (3)	O3'—C12'—C11'	131.0 (3)
O3—C12—C11	129.7 (3)	O3'—C12'—C13'	121.0 (3)
C13—C12—C11	108.0	C11'—C12'—C13'	108.0
O4—C13—C12	130.1 (3)	O4'—C13'—C14'	119.3 (3)
O4—C13—C14	121.9 (3)	O4'—C13'—C12'	132.7 (3)
C12—C13—C14	108.0	C14'—C13'—C12'	108.0
O5—C14—C13	122.4 (4)	O5'—C14'—C13'	123.8 (3)
O5—C14—C10	129.6 (4)	O5'—C14'—C10'	128.2 (3)
C13—C14—C10	108.0	C13'—C14'—C10'	108.0
O3—C15—H15A	109.5	O3'—C15'—H15D	109.5
O3—C15—H15B	109.5	O3'—C15'—H15E	109.5
H15A—C15—H15B	109.5	H15D—C15'—H15E	109.5
O3—C15—H15C	109.5	O3'—C15'—H15F	109.5
H15A—C15—H15C	109.5	H15D—C15'—H15F	109.5
H15B—C15—H15C	109.5	H15E—C15'—H15F	109.5
O4—C16—H16A	109.5	O4'—C16'—H16D	109.5
O4—C16—H16B	109.5	O4'—C16'—H16E	109.5
H16A—C16—H16B	109.5	H16D—C16'—H16E	109.5
O4—C16—H16C	109.5	O4'—C16'—H16F	109.5
H16A—C16—H16C	109.5	H16D—C16'—H16F	109.5
H16B—C16—H16C	109.5	H16E—C16'—H16F	109.5

C6—C1—C2—C3	0.0	C6'—C1'—C2'—C3'	0.0
C1—C2—C3—C4	0.0	C1'—C2'—C3'—C4'	0.0
C2—C3—C4—C5	0.0	C2'—C3'—C4'—C5'	0.0
C3—C4—C5—C6	0.0	C3'—C4'—C5'—C6'	0.0
C4—C5—C6—C1	0.0	C4'—C5'—C6'—C1'	0.0
C4—C5—C6—C7	−179.0 (5)	C4'—C5'—C6'—C7'	−179.9 (5)
C2—C1—C6—C5	0.0	C2'—C1'—C6'—C5'	0.0
C2—C1—C6—C7	178.9 (5)	C2'—C1'—C6'—C7'	179.9 (5)
C5—C6—C7—C8	−179.2 (6)	C5'—C6'—C7'—C8'	−178.5 (6)
C1—C6—C7—C8	1.9 (7)	C1'—C6'—C7'—C8'	1.6 (7)
C6—C7—C8—C9	179.8 (5)	C6'—C7'—C8'—C9'	−179.2 (5)
C7—C8—C9—O1	−0.1 (9)	C7'—C8'—C9'—O1'	0.7 (9)
C7—C8—C9—C10	−179.2 (5)	C7'—C8'—C9'—C10'	−179.3 (6)
O1—C9—C10—C11	−0.4 (5)	O1'—C9'—C10'—C11'	0.1 (5)
C8—C9—C10—C11	178.7 (5)	C8'—C9'—C10'—C11'	−179.9 (5)
O1—C9—C10—C14	178.4 (3)	O1'—C9'—C10'—C14'	−178.5 (3)
C8—C9—C10—C14	−2.5 (7)	C8'—C9'—C10'—C14'	1.5 (7)
C9—C10—C11—O2	0.4 (5)	C9'—C10'—C11'—O2'	0.2 (5)
C14—C10—C11—O2	−178.6 (5)	C14'—C10'—C11'—O2'	179.2 (4)
C9—C10—C11—C12	179.0 (4)	C9'—C10'—C11'—C12'	−178.9 (4)
C14—C10—C11—C12	0.0	C14'—C10'—C11'—C12'	0.0
C15—O3—C12—C13	−176.5 (6)	C15'—O3'—C12'—C11'	−10.5 (7)
C15—O3—C12—C11	5.5 (8)	C15'—O3'—C12'—C13'	168.5 (5)
O2—C11—C12—O3	−3.2 (5)	O2'—C11'—C12'—O3'	−0.1 (5)
C10—C11—C12—O3	178.2 (5)	C10'—C11'—C12'—O3'	179.1 (5)
O2—C11—C12—C13	178.7 (5)	O2'—C11'—C12'—C13'	−179.2 (4)
C10—C11—C12—C13	0.0	C10'—C11'—C12'—C13'	0.0
C16—O4—C13—C12	−2.2 (7)	C16'—O4'—C13'—C14'	177.9 (7)
C16—O4—C13—C14	178.9 (6)	C16'—O4'—C13'—C12'	−2.3 (8)
O3—C12—C13—O4	2.6 (5)	O3'—C12'—C13'—O4'	1.0 (5)
C11—C12—C13—O4	−179.0 (4)	C11'—C12'—C13'—O4'	−179.8 (5)
O3—C12—C13—C14	−178.4 (4)	O3'—C12'—C13'—C14'	−179.2 (4)
C11—C12—C13—C14	0.0	C11'—C12'—C13'—C14'	0.0
O4—C13—C14—O5	−0.4 (4)	O4'—C13'—C14'—O5'	−0.9 (5)
C12—C13—C14—O5	−179.5 (4)	C12'—C13'—C14'—O5'	179.3 (4)
O4—C13—C14—C10	179.1 (4)	O4'—C13'—C14'—C10'	179.8 (4)
C12—C13—C14—C10	0.0	C12'—C13'—C14'—C10'	0.0
C9—C10—C14—O5	0.5 (5)	C9'—C10'—C14'—O5'	−0.5 (6)
C11—C10—C14—O5	179.5 (4)	C11'—C10'—C14'—O5'	−179.3 (4)
C9—C10—C14—C13	−178.9 (4)	C9'—C10'—C14'—C13'	178.8 (4)
C11—C10—C14—C13	0.0	C11'—C10'—C14'—C13'	0.0

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.84	1.93	2.600 (5)	136
O1′—H1′···O2′	0.84	1.97	2.623 (4)	134
C2—H2···O2ⁱ	0.95	2.26	3.091 (8)	145
C16′—H16D···O1′ⁱⁱ	0.98	2.05	2.885 (11)	142

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄O₅
M_r	286.27
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	7.3195 (5), 9.8635 (7), 18.6724 (11)
β (°)	96.586 (6)
V (Å³)	1339.17 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.20 × 0.20 × 0.10

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.979, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	8436, 2369, 1965
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.190, 1.05
No. of reflections	2369
No. of parameters	308
No. of restraints	30
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.34

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.84	1.93	2.600 (5)	136
O1'—H1'···O2'	0.84	1.97	2.623 (4)	134
C2—H2···O2ⁱ	0.95	2.26	3.091 (8)	145
C16'—H16D···O1'ⁱⁱ	0.98	2.05	2.885 (11)	142

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

Acknowledgements

This work was carried under the aegis of a University of Malaya–CNRS (France) collaborative framework. We thank the University of Malaya (grant No. RG045/11BIO) for financial support.

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Kiang, A. K., Lee, H. H. & Sim, K. Y. (1962). J. Chem. Soc. pp. 4338–4345. CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Syah, Y. M., Suastri, N. S., Latip, J. & Yamin, B. M. (2005). Acta Cryst. E61, o1530–o1531. Web of Science CSD CrossRef IUCr Journals 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 67| Part 6| June 2011| Page o1544

doi:10.1107/S1600536811019386

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

Whole-mol­ecule disordered (E)-2-(1-hy­dr­oxy-3-phenylprop-2-en-1-yl­­idene)-4,5-dimeth­oxycyclo­pent-4-ene-1,3-dione isolated from Lindera oxyphylla (Lauraceae)

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Whole-molecule disordered (E)-2-(1-hydroxy-3-phenylprop-2-en-1-ylidene)-4,5-dimethoxycyclopent-4-ene-1,3-dione isolated from Lindera oxyphylla (Lauraceae)