A triclinic polymorph of (E)-2-(1-hy­droxy-3-phenyl­prop-2-en-1-yl­idene)-4,5-dimeth­oxy­cyclo­pent-4-ene-1,3-dione

Hosseinzadeh, M.; Mukhtar, M.R.; Khalilzadeh, M.A.; Khaledi, H.

doi:10.1107/S1600536812001043

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o453

doi:10.1107/S1600536812001043

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A triclinic polymorph of (E)-2-(1-hydroxy-3-phenylprop-2-en-1-ylidene)-4,5-dimethoxycyclopent-4-ene-1,3-dione

Masoumeh Hosseinzadeh,^a Mat Ropi Mukhtar,^a Mohammad Ali Khalilzadeh ^b and Hamid Khaledi ^c ^*

^aCentre for Natural Products and Drug Discovery, Department of Chemistry, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia, ^bDepartment of Chemistry, Science and Research Branch, Islamic Azad University, Mazandaran, Iran, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: khaledi@siswa.um.edu.my

(Received 4 January 2012; accepted 10 January 2012; online 18 January 2012)

The title compound, C₁₆H₁₄O₅, is a triclinic polymorph of a previously reported monoclinic structure [Hosseinzadeh et al. (2011 ). Acta Cryst. E67, o1544]. The molecule is roughly planar, the r.m.s. deviation from the least-squares plane of all non-H atoms being 0.092 Å. In the crystal, adjacent molecules are linked through C—H⋯O hydrogen bonds into an infinite two-dimensional network parallel to (011). The layers are further connected via C—H⋯π interactions, forming a three-dimensional structure. Intramolecular O—H⋯O and C—H⋯O hydrogen bonds are also observed.

Related literature

For the crystal structure of the monoclinic polymorph, see: Hosseinzadeh et al. (2011).

Experimental

Crystal data

C₁₆H₁₄O₅
M_r = 286.27
Triclinic, $[P \overline 1]$
a = 5.4055 (2) Å
b = 11.2731 (3) Å
c = 11.6441 (3) Å
α = 72.070 (1)°
β = 83.088 (1)°
γ = 77.760 (1)°
V = 658.59 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 100 K
0.26 × 0.19 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.973, T_max = 0.988
3340 measured reflections
2300 independent reflections
2041 reflections with I > 2σ(I)
R_int = 0.010

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.098
S = 1.07
2300 reflections
195 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.89 (2)	1.87 (2)	2.6802 (14)	150 (2)
C8—H8⋯O5	0.95	2.49	3.1015 (17)	122
C15—H15B⋯O3ⁱ	0.98	2.49	3.3751 (18)	151
C15—H15C⋯O2ⁱⁱ	0.98	2.49	3.3789 (18)	150
C16—H16A⋯O5ⁱⁱⁱ	0.98	2.56	3.4143 (19)	145
C15—H15A⋯Cg^iv	0.98	2.71	3.5728 (17)	147
Symmetry codes: (i) -x+2, -y-1, -z+1; (ii) x+1, y, z; (iii) -x+2, -y, -z; (iv) x+1, y-1, z.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ) and XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812001043/pv2504sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812001043/pv2504Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812001043/pv2504Isup3.cml

checkCIF report

Comment top

The crystal structure of the title compound isolated from Lindera pipericarpa recrystallized from dichloromethane has been reported recently in monoclinic system with gross disorder (Hosseinzadeh et al., 2011). In order to obtain a crystal of better quality, we recrystallized the compound from a different solvent, i. e., dimethyl sulfoxide (DMSO). The preliminary crystallographic data showed that the new crystals were formed in a triclinic system. The crystal structure of the new polymorph in the triclinic system is reported in this paper.

The title molecule (Fig. 1) is essentially planar [maximum atomic deviation = 0.2836 (13) Å for C16] and shows a higher deviation from planarity than is shown by the monoclinic structure [maximum atomic deviation = 0.064 (5) Å]. The crystal shows a three-dimensional supramolecular strucure formed by intermolecular C—H···O (Fig. 2) and C—H···π interactions (Table 1). In addition, intramolecular O—H···O and C—H···O hydrogen bonds are present.

Related literature top

For the crystal structure of the monoclinic polymorph, see: Hosseinzadeh et al. (2011).

Experimental top

The isolation of the title compound from Lindera pipericarpa (Lauraceae) has been reported recently (Hosseinzadeh et al., 2011). Recrystallization of the title compound from DMSO at room temperature resulted in the formation of the triclinic polymorph.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001) and XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. Molecular structure of the title compound with displacement ellipsoids drawn at 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. Intra- and intermolecular O—H···O and C—H···O hydrogen bonding in the structure. Symmetry codes: i = -x + 2, -y - 1; iii = -x + 2, -y, -z; v = x-1, y, z.

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

Crystal data top

C₁₆H₁₄O₅	Z = 2
M_r = 286.27	F(000) = 300
Triclinic, P1	D_x = 1.444 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.4055 (2) Å	Cell parameters from 2073 reflections
b = 11.2731 (3) Å	θ = 2.3–29.6°
c = 11.6441 (3) Å	µ = 0.11 mm⁻¹
α = 72.070 (1)°	T = 100 K
β = 83.088 (1)°	Block, orange
γ = 77.760 (1)°	0.26 × 0.19 × 0.11 mm
V = 658.59 (3) Å³

Data collection top

Bruker APEXII CCD diffractometer	2300 independent reflections
Radiation source: fine-focus sealed tube	2041 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.010
ϕ and ω scans	θ_max = 25.3°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→4
T_min = 0.973, T_max = 0.988	k = −13→13
3340 measured reflections	l = −13→13

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0544P)² + 0.2122P] where P = (F_o² + 2F_c²)/3
2300 reflections	(Δ/σ)_max < 0.001
195 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₁₆H₁₄O₅	γ = 77.760 (1)°
M_r = 286.27	V = 658.59 (3) Å³
Triclinic, P1	Z = 2
a = 5.4055 (2) Å	Mo Kα radiation
b = 11.2731 (3) Å	µ = 0.11 mm⁻¹
c = 11.6441 (3) Å	T = 100 K
α = 72.070 (1)°	0.26 × 0.19 × 0.11 mm
β = 83.088 (1)°

Data collection top

Bruker APEXII CCD diffractometer	2300 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2041 reflections with I > 2σ(I)
T_min = 0.973, T_max = 0.988	R_int = 0.010
3340 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.18 e Å⁻³
2300 reflections	Δρ_min = −0.25 e Å⁻³
195 parameters

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	U_iso*/U_eq
O1	0.17619 (19)	0.04462 (10)	0.41452 (9)	0.0200 (3)
H1	0.223 (3)	−0.0369 (18)	0.4540 (17)	0.030*
O2	0.46326 (19)	−0.18778 (9)	0.47978 (9)	0.0197 (2)
O3	0.9457 (2)	−0.32456 (9)	0.43272 (9)	0.0213 (3)
O4	1.21886 (19)	−0.14869 (9)	0.22747 (9)	0.0204 (3)
O5	0.84852 (19)	0.09819 (9)	0.16019 (9)	0.0203 (3)
C1	0.0432 (3)	0.42536 (13)	0.20660 (13)	0.0175 (3)
C2	0.2093 (3)	0.48875 (14)	0.11858 (13)	0.0204 (3)
H2	0.3715	0.4439	0.1005	0.024*
C3	0.1391 (3)	0.61581 (14)	0.05797 (13)	0.0217 (3)
H3	0.2530	0.6575	−0.0018	0.026*
C4	−0.0961 (3)	0.68287 (14)	0.08356 (14)	0.0231 (3)
H4	−0.1438	0.7702	0.0412	0.028*
C5	−0.2616 (3)	0.62210 (14)	0.17131 (15)	0.0251 (4)
H5	−0.4224	0.6680	0.1897	0.030*
C6	−0.1921 (3)	0.49427 (14)	0.23222 (14)	0.0215 (3)
H6	−0.3065	0.4532	0.2922	0.026*
C7	0.1065 (3)	0.29054 (13)	0.27304 (13)	0.0182 (3)
H7	−0.0179	0.2566	0.3317	0.022*
C8	0.3218 (3)	0.20994 (13)	0.25971 (12)	0.0173 (3)
H8	0.4496	0.2399	0.2009	0.021*
C9	0.3647 (3)	0.07895 (13)	0.33234 (12)	0.0165 (3)
C10	0.5791 (3)	−0.00870 (13)	0.32366 (12)	0.0165 (3)
C11	0.6157 (3)	−0.13911 (13)	0.40132 (12)	0.0163 (3)
C12	0.8704 (3)	−0.20369 (13)	0.36824 (13)	0.0173 (3)
C13	0.9804 (3)	−0.12165 (13)	0.27535 (12)	0.0165 (3)
C14	0.8051 (3)	0.00484 (13)	0.24166 (12)	0.0159 (3)
C15	1.1901 (3)	−0.39160 (13)	0.39974 (14)	0.0216 (3)
H15A	1.1943	−0.3912	0.3152	0.032*
H15B	1.2173	−0.4794	0.4520	0.032*
H15C	1.3240	−0.3496	0.4097	0.032*
C16	1.2894 (3)	−0.07311 (14)	0.10899 (13)	0.0235 (3)
H16A	1.1761	−0.0760	0.0506	0.035*
H16B	1.4646	−0.1066	0.0861	0.035*
H16C	1.2757	0.0148	0.1094	0.035*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0194 (6)	0.0182 (5)	0.0188 (5)	−0.0031 (4)	0.0024 (4)	−0.0018 (4)
O2	0.0221 (6)	0.0194 (5)	0.0170 (5)	−0.0070 (4)	0.0012 (4)	−0.0029 (4)
O3	0.0243 (6)	0.0130 (5)	0.0212 (5)	−0.0004 (4)	0.0015 (4)	−0.0005 (4)
O4	0.0181 (6)	0.0179 (5)	0.0188 (5)	−0.0011 (4)	0.0028 (4)	0.0010 (4)
O5	0.0219 (6)	0.0161 (5)	0.0187 (5)	−0.0027 (4)	0.0019 (4)	−0.0007 (4)
C1	0.0187 (8)	0.0187 (7)	0.0162 (7)	−0.0039 (6)	−0.0020 (6)	−0.0059 (6)
C2	0.0188 (8)	0.0199 (7)	0.0209 (7)	−0.0007 (6)	0.0015 (6)	−0.0065 (6)
C3	0.0226 (8)	0.0202 (7)	0.0207 (8)	−0.0056 (6)	0.0028 (6)	−0.0041 (6)
C4	0.0235 (8)	0.0163 (7)	0.0258 (8)	−0.0011 (6)	−0.0030 (6)	−0.0020 (6)
C5	0.0177 (8)	0.0214 (8)	0.0323 (9)	0.0011 (6)	−0.0001 (6)	−0.0059 (7)
C6	0.0181 (8)	0.0205 (7)	0.0236 (8)	−0.0042 (6)	0.0023 (6)	−0.0040 (6)
C7	0.0195 (8)	0.0194 (7)	0.0162 (7)	−0.0051 (6)	−0.0010 (6)	−0.0048 (6)
C8	0.0183 (7)	0.0174 (7)	0.0155 (7)	−0.0039 (6)	−0.0009 (6)	−0.0035 (6)
C9	0.0188 (8)	0.0185 (7)	0.0135 (7)	−0.0059 (6)	−0.0001 (6)	−0.0049 (6)
C10	0.0202 (8)	0.0154 (7)	0.0139 (7)	−0.0045 (6)	−0.0010 (6)	−0.0034 (6)
C11	0.0201 (7)	0.0178 (7)	0.0133 (7)	−0.0063 (6)	−0.0010 (6)	−0.0058 (6)
C12	0.0220 (8)	0.0131 (7)	0.0163 (7)	−0.0030 (6)	−0.0028 (6)	−0.0032 (6)
C13	0.0175 (7)	0.0162 (7)	0.0157 (7)	−0.0023 (6)	−0.0012 (6)	−0.0052 (6)
C14	0.0184 (7)	0.0151 (7)	0.0146 (7)	−0.0037 (5)	−0.0026 (5)	−0.0042 (6)
C15	0.0201 (8)	0.0153 (7)	0.0256 (8)	−0.0011 (6)	0.0012 (6)	−0.0029 (6)
C16	0.0217 (8)	0.0226 (8)	0.0182 (8)	0.0001 (6)	0.0054 (6)	0.0005 (6)

Geometric parameters (Å, º) top

O1—C9	1.3447 (17)	C5—H5	0.9500
O1—H1	0.89 (2)	C6—H6	0.9500
O2—C11	1.2316 (17)	C7—C8	1.342 (2)
O3—C12	1.3396 (17)	C7—H7	0.9500
O3—C15	1.4480 (17)	C8—C9	1.443 (2)
O4—C13	1.3528 (17)	C8—H8	0.9500
O4—C16	1.4360 (17)	C9—C10	1.370 (2)
O5—C14	1.2244 (17)	C10—C11	1.4558 (19)
C1—C6	1.394 (2)	C10—C14	1.461 (2)
C1—C2	1.402 (2)	C11—C12	1.481 (2)
C1—C7	1.465 (2)	C12—C13	1.357 (2)
C2—C3	1.380 (2)	C13—C14	1.5026 (19)
C2—H2	0.9500	C15—H15A	0.9800
C3—C4	1.384 (2)	C15—H15B	0.9800
C3—H3	0.9500	C15—H15C	0.9800
C4—C5	1.387 (2)	C16—H16A	0.9800
C4—H4	0.9500	C16—H16B	0.9800
C5—C6	1.388 (2)	C16—H16C	0.9800

C9—O1—H1	107.7 (12)	C10—C9—C8	125.01 (13)
C12—O3—C15	118.30 (11)	C9—C10—C11	122.86 (13)
C13—O4—C16	119.37 (11)	C9—C10—C14	129.76 (13)
C6—C1—C2	118.33 (13)	C11—C10—C14	107.39 (12)
C6—C1—C7	118.69 (13)	O2—C11—C10	126.61 (13)
C2—C1—C7	122.98 (13)	O2—C11—C12	125.92 (13)
C3—C2—C1	120.58 (14)	C10—C11—C12	107.47 (12)
C3—C2—H2	119.7	O3—C12—C13	133.61 (13)
C1—C2—H2	119.7	O3—C12—C11	117.03 (12)
C2—C3—C4	120.50 (14)	C13—C12—C11	109.35 (12)
C2—C3—H3	119.8	O4—C13—C12	124.39 (13)
C4—C3—H3	119.8	O4—C13—C14	125.90 (12)
C3—C4—C5	119.72 (14)	C12—C13—C14	109.54 (12)
C3—C4—H4	120.1	O5—C14—C10	128.48 (13)
C5—C4—H4	120.1	O5—C14—C13	125.30 (13)
C4—C5—C6	119.99 (14)	C10—C14—C13	106.22 (11)
C4—C5—H5	120.0	O3—C15—H15A	109.5
C6—C5—H5	120.0	O3—C15—H15B	109.5
C5—C6—C1	120.88 (13)	H15A—C15—H15B	109.5
C5—C6—H6	119.6	O3—C15—H15C	109.5
C1—C6—H6	119.6	H15A—C15—H15C	109.5
C8—C7—C1	126.79 (13)	H15B—C15—H15C	109.5
C8—C7—H7	116.6	O4—C16—H16A	109.5
C1—C7—H7	116.6	O4—C16—H16B	109.5
C7—C8—C9	121.76 (13)	H16A—C16—H16B	109.5
C7—C8—H8	119.1	O4—C16—H16C	109.5
C9—C8—H8	119.1	H16A—C16—H16C	109.5
O1—C9—C10	119.60 (13)	H16B—C16—H16C	109.5
O1—C9—C8	115.38 (12)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.89 (2)	1.87 (2)	2.6802 (14)	150 (2)
C8—H8···O5	0.95	2.49	3.1015 (17)	122
C16—H16C···O5	0.98	2.38	2.8600 (18)	110
C15—H15B···O3ⁱ	0.98	2.49	3.3751 (18)	151
C15—H15C···O2ⁱⁱ	0.98	2.49	3.3789 (18)	150
C16—H16A···O5ⁱⁱⁱ	0.98	2.56	3.4143 (19)	145
C15—H15A···Cg^iv	0.98	2.71	3.5728 (17)	147

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄O₅
M_r	286.27
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	5.4055 (2), 11.2731 (3), 11.6441 (3)
α, β, γ (°)	72.070 (1), 83.088 (1), 77.760 (1)
V (Å³)	658.59 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.26 × 0.19 × 0.11

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.973, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	3340, 2300, 2041
R_int	0.010
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.098, 1.07
No. of reflections	2300
No. of parameters	195
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.25

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), X-SEED (Barbour, 2001) and XP in SHELXTL (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of C1–C6 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.89 (2)	1.87 (2)	2.6802 (14)	150 (2)
C8—H8···O5	0.95	2.49	3.1015 (17)	122.4
C16—H16C···O5	0.98	2.38	2.8600 (18)	109.6
C15—H15B···O3ⁱ	0.98	2.49	3.3751 (18)	150.8
C15—H15C···O2ⁱⁱ	0.98	2.49	3.3789 (18)	150.4
C16—H16A···O5ⁱⁱⁱ	0.98	2.56	3.4143 (19)	145.1
C15—H15A···Cg^iv	0.98	2.71	3.5728 (17)	147.0

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

Acknowledgements

Financial support from the University of Malaya is highly appreciated (PPP grant No. PS265/2010B).

References

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Volume 68| Part 2| February 2012| Page o453

doi:10.1107/S1600536812001043

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

A triclinic polymorph of (E)-2-(1-hy­dr­oxy-3-phenyl­prop-2-en-1-yl­­idene)-4,5-dimeth­­oxy­cyclo­pent-4-ene-1,3-dione

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

A triclinic polymorph of (E)-2-(1-hydroxy-3-phenylprop-2-en-1-ylidene)-4,5-dimethoxycyclopent-4-ene-1,3-dione