Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 10| October 2012| Page o2909
https://doi.org/10.1107/S1600536812038007

(E)-1-[4-(Hex­yl­oxy)phen­yl]-3-(2-hy­dr­oxy­phen­yl)prop-2-en-1-one

Siti Muhaini Haris Fadzillah,a Zainab Ngaini,a Hasnain Hussain,b Ibrahim Abdul Razakc*‡ and Safra Izuani Jama Asikc

aDepartment of Chemistry, Faculty of Resource Science and Technology, Universiti Malaysia Sarawak, 94300 Kota Samarahan, Sarawak, Malaysia, bDepartment of Molecular Biology, Faculty of Resource Science and Technology, Universiti Malaysia Sarawak, 94300 Kota Samarahan, Sarawak, Malaysia, and cSchool of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: arazaki@usm.my

(Received 29 August 2012; accepted 4 September 2012; online 8 September 2012)

In the title compound, C21H24O3, the enone moiety adopts an s-cis conformation and the dihedral angle between the benzene rings is 12.89 (6)°. The hex­yloxy tail adopts an extended conformation. In the crystal, inversion dimers are linked by pairs of O—H⋯O hydrogen bonds and pairs of C—H⋯O inter­actions, forming two R22(7) and one R22(10) loops. The dimers are then arranged into sheets lying parallel to (201) and weak C—H⋯π inter­actions consolidate the packing.

Related literature

For a related structure and background to the biological properties of chalcones, see: Ngaini et al. (2011[Ngaini, Z., Fadzillah, S. M. H., Hussain, H., Razak, I. A. & Fun, H.-K. (2011). Acta Cryst. E67, o169-o170.]). For related structures, see: Razak et al. (2009[Razak, I. A., Fun, H.-K., Ngaini, Z., Rahman, N. I. A. & Hussain, H. (2009). Acta Cryst. E65, o1439-o1440.]); Ngaini et al. (2010[Ngaini, Z., Fadzillah, S. M. H., Hussain, H., Razak, I. A. & Fun, H.-K. (2010). Acta Cryst. E66, o3275-o3276.]). For graph-set theory, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986)[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.].

[Scheme 1]

Experimental

Crystal data

  • C21H24O3

  • Mr = 324.40

  • Triclinic, [P \overline 1]

  • a = 7.485 (2) Å

  • b = 10.834 (3) Å

  • c = 11.673 (3) Å

  • α = 73.858 (5)°

  • β = 77.961 (6)°

  • γ = 76.941 (6)°

  • V = 874.9 (4) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 100 K

  • 0.47 × 0.14 × 0.12 mm
Data collection

  • Bruker APEX DUO CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.963, Tmax = 0.991

  • 17565 measured reflections

  • 4576 independent reflections

  • 3781 reflections with I > 2σ(I)

  • Rint = 0.026
Refinement

  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.133

  • S = 1.02

  • 4576 reflections

  • 222 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.39 e Å−3

  • Δρmin = −0.23 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
O2—H1O2⋯O1i 0.94 (2) 1.78 (2) 2.6862 (15) 163.3 (19)
C7—H7A⋯O2i 0.93 2.37 3.2526 (18) 158
C16—H16A⋯Cg1ii 0.97 2.91 3.6117 (16) 130
Symmetry codes: (i) -x, -y+2, -z+2; (ii) -x+1, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812038007/hb6948sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812038007/hb6948Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812038007/hb6948Isup3.cml

checkCIF report


Comment top

As part of our ongoing studies of the biological activities of chalcone derivatives (Ngaini et al., 2011), the title compound has been synthesised and tested against E. coli ATCC 8739 and showed anti-microbial activity. We now describe its crystal structure.

In the title of chalcone derivative, Fig. 1, the conformation of the enone (O1/C7–C8) moiety is s-cis with the C7–C8–C9–o1 torsion angle being 0.89 (18)°. The least-square plane through enone moeity make dihedral angles of 7.57 (7)° and 8.18 (7)° with (C10–C15 and C1–C6) benzene rings, respectively. The dihedral angle between the two benzene rings is 12.89 (6)°.

The widening of C9–C10–C15, C6–C7–C8 and C1–C6–C7 angles to 123.98 (10)°, 126.08 (10)° and 123.26 (10) respectively, are the consequences of the short contact between H15A and H8A (2.075 Å) as well as H8A and H1A (2.214 Å). Likewise, the slight opening of O3–C13–C14 to 125.30 (10)° is the result of the strain induced by close H14A···H16A (2.253 Å) interatomic contact. Similar features were also observed in closely related structures (Razak et al., 2009; Ngaini et al., 2010; Ngaini et al., 2011).

The zigzag alkoxyl tail is assumed as a trans conformation. The torsion angle C16–O3–C13–C14 of 2.51 (16)° implies that the alkoxyl tail is roughly co-planar with the attached benzene ring. However, it is actually twisted away from planarity as shown by the torsion angle of 166.42 (9)° for C13–O3–C16–C17. The twist about C17–C18 bond is indicated by C16–C17–C18–C19 torsion angle of 173.51 (9)°.

In the crystal packing of (Fig. 2), the molecules are connected by intermolecular interactions O2—H1O2···O1 and C7—H7A···O2 hydrogen bonds to form two R22(7) and one R22(10) rings motif which linked the molecules into pairs which are then arranged into sheets parallel to (201) plane. Furthermore, the crystal packing features weak C—H···π interactions (Table 1) with the distance of 3.6117 (16) Å.

Related literature top

For a related structure and background to the biological properties of chalcones, see: Ngaini et al. (2011). For related structures, see: Razak et al. (2009); Ngaini et al. (2010). For graph-set theory, see: Bernstein et al. (1995). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

A mixture of 2-hydroxybenzaldehyde (1.46 ml, 12 mmol), and 4-hexyloxyacetophenone (2.64 g, 12 mmol) and KOH (2.42 g, 43 mmol) in methanol (50 ml) was heated at reflux for 24 h. The reaction was cooled to room temperature and acidified with cold diluted HCl (2N). The resulting precipitate was filtered, washed and dried. After redissolving in hexane-ethanol (7:1) followed by few days of slow evaporation, yellow blocks were collected.

Refinement top

The O-bound H atom was located in a difference Fourier map and refined freely with O–H = 0.94 (2) Å. The remaining H atoms were placed in calculated positions with C–H = 0.93–0.97 Å. The Uiso values were constrained to be 1.5Ueq (methyl-H atom) and 1.2Ueq (other H atoms). The rotating model group was applied for the methyl group.

Structure description top

As part of our ongoing studies of the biological activities of chalcone derivatives (Ngaini et al., 2011), the title compound has been synthesised and tested against E. coli ATCC 8739 and showed anti-microbial activity. We now describe its crystal structure.

In the title of chalcone derivative, Fig. 1, the conformation of the enone (O1/C7–C8) moiety is s-cis with the C7–C8–C9–o1 torsion angle being 0.89 (18)°. The least-square plane through enone moeity make dihedral angles of 7.57 (7)° and 8.18 (7)° with (C10–C15 and C1–C6) benzene rings, respectively. The dihedral angle between the two benzene rings is 12.89 (6)°.

The widening of C9–C10–C15, C6–C7–C8 and C1–C6–C7 angles to 123.98 (10)°, 126.08 (10)° and 123.26 (10) respectively, are the consequences of the short contact between H15A and H8A (2.075 Å) as well as H8A and H1A (2.214 Å). Likewise, the slight opening of O3–C13–C14 to 125.30 (10)° is the result of the strain induced by close H14A···H16A (2.253 Å) interatomic contact. Similar features were also observed in closely related structures (Razak et al., 2009; Ngaini et al., 2010; Ngaini et al., 2011).

The zigzag alkoxyl tail is assumed as a trans conformation. The torsion angle C16–O3–C13–C14 of 2.51 (16)° implies that the alkoxyl tail is roughly co-planar with the attached benzene ring. However, it is actually twisted away from planarity as shown by the torsion angle of 166.42 (9)° for C13–O3–C16–C17. The twist about C17–C18 bond is indicated by C16–C17–C18–C19 torsion angle of 173.51 (9)°.

In the crystal packing of (Fig. 2), the molecules are connected by intermolecular interactions O2—H1O2···O1 and C7—H7A···O2 hydrogen bonds to form two R22(7) and one R22(10) rings motif which linked the molecules into pairs which are then arranged into sheets parallel to (201) plane. Furthermore, the crystal packing features weak C—H···π interactions (Table 1) with the distance of 3.6117 (16) Å.

For a related structure and background to the biological properties of chalcones, see: Ngaini et al. (2011). For related structures, see: Razak et al. (2009); Ngaini et al. (2010). For graph-set theory, see: Bernstein et al. (1995). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The structure of the title compound, showing 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. The crystal packing, viewed along the a-axis, showing the molecules in pairs, arranged into sheets parallel to (201) plane. Hydrogen bonds are shown as dashed lines.
(E)-1-[4-(Hexyloxy)phenyl]-3-(2-hydroxyphenyl)prop-2-en-1-one top
Crystal data top
C21H24O3Z = 2
Mr = 324.40F(000) = 348
Triclinic, P1Dx = 1.231 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.485 (2) ÅCell parameters from 6758 reflections
b = 10.834 (3) Åθ = 2.4–31.7°
c = 11.673 (3) ŵ = 0.08 mm−1
α = 73.858 (5)°T = 100 K
β = 77.961 (6)°Block, yellow
γ = 76.941 (6)°0.47 × 0.14 × 0.12 mm
V = 874.9 (4) Å3
Data collection top
Bruker APEX DUO CCD
diffractometer		4576 independent reflections
Radiation source: fine-focus sealed tube3781 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
φ and ω scansθmax = 29.0°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		h = −10→10
Tmin = 0.963, Tmax = 0.991k = −14→14
17565 measured reflectionsl = −15→15
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.077P)2 + 0.2082P]
where P = (Fo2 + 2Fc2)/3
4576 reflections(Δ/σ)max < 0.001
222 parametersΔρmax = 0.39 e Å−3
0 restraintsΔρmin = −0.23 e Å−3
Crystal data top
C21H24O3γ = 76.941 (6)°
Mr = 324.40V = 874.9 (4) Å3
Triclinic, P1Z = 2
a = 7.485 (2) ÅMo Kα radiation
b = 10.834 (3) ŵ = 0.08 mm−1
c = 11.673 (3) ÅT = 100 K
α = 73.858 (5)°0.47 × 0.14 × 0.12 mm
β = 77.961 (6)°
Data collection top
Bruker APEX DUO CCD
diffractometer		4576 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		3781 reflections with I > 2σ(I)
Tmin = 0.963, Tmax = 0.991Rint = 0.026
17565 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.133H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.39 e Å−3
4576 reflectionsΔρmin = −0.23 e Å−3
222 parameters
Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
xyzUiso*/Ueq
O10.10199 (12)0.82681 (7)0.77465 (7)0.02537 (19)
O20.05000 (12)1.13926 (7)1.00412 (7)0.02580 (19)
O30.26974 (11)0.74559 (8)0.24879 (7)0.02478 (19)
C10.23994 (15)1.29725 (10)0.70042 (10)0.0229 (2)
H1A0.28481.27730.62600.027*
C20.24424 (16)1.41983 (11)0.71304 (11)0.0261 (2)
H2A0.29221.48120.64770.031*
C30.17661 (16)1.45074 (10)0.82374 (11)0.0256 (2)
H3A0.17631.53380.83180.031*
C40.10963 (15)1.35851 (10)0.92229 (10)0.0232 (2)
H4A0.06551.37940.99640.028*
C50.10858 (14)1.23422 (10)0.91002 (10)0.0198 (2)
C60.16962 (14)1.20282 (10)0.79729 (10)0.0194 (2)
C70.15502 (14)1.07449 (10)0.78689 (10)0.0205 (2)
H7A0.12111.01450.85810.025*
C80.18600 (15)1.03496 (10)0.68408 (10)0.0226 (2)
H8A0.22661.09120.61190.027*
C90.15789 (14)0.90539 (10)0.68181 (10)0.0201 (2)
C100.19366 (14)0.86986 (10)0.56431 (10)0.0199 (2)
C110.14263 (15)0.75378 (10)0.56113 (10)0.0223 (2)
H11A0.08960.70180.63200.027*
C120.17005 (15)0.71606 (11)0.45458 (10)0.0239 (2)
H12A0.13490.63920.45410.029*
C130.25034 (14)0.79245 (10)0.34708 (10)0.0213 (2)
C140.30205 (15)0.90824 (11)0.34783 (10)0.0235 (2)
H14A0.35500.96000.27670.028*
C150.27332 (15)0.94525 (10)0.45625 (10)0.0232 (2)
H15A0.30821.02220.45670.028*
C160.35636 (15)0.81399 (11)0.13354 (10)0.0226 (2)
H16A0.46990.83760.14150.027*
H16B0.27340.89290.10060.027*
C170.39770 (15)0.72005 (10)0.05308 (10)0.0225 (2)
H17A0.28200.69850.04640.027*
H17B0.47420.64000.09070.027*
C180.49635 (15)0.77343 (11)−0.07282 (10)0.0227 (2)
H18A0.60550.8039−0.06670.027*
H18B0.41440.8473−0.11470.027*
C190.55427 (16)0.66941 (11)−0.14528 (10)0.0243 (2)
H19A0.63620.5961−0.10270.029*
H19B0.44460.6381−0.14910.029*
C200.65178 (16)0.71628 (12)−0.27296 (10)0.0275 (2)
H20A0.75970.7501−0.26990.033*
H20B0.56850.7871−0.31710.033*
C210.7131 (2)0.60782 (14)−0.34014 (12)0.0375 (3)
H21A0.78170.6400−0.41800.056*
H21B0.60580.5795−0.35000.056*
H21C0.79040.5356−0.29470.056*
H1O20.001 (3)1.1676 (18)1.0758 (18)0.058 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0357 (4)0.0204 (4)0.0196 (4)−0.0082 (3)−0.0005 (3)−0.0046 (3)
O20.0370 (4)0.0201 (4)0.0197 (4)−0.0094 (3)0.0018 (3)−0.0052 (3)
O30.0294 (4)0.0283 (4)0.0181 (4)−0.0101 (3)0.0017 (3)−0.0081 (3)
C10.0254 (5)0.0209 (5)0.0214 (5)−0.0045 (4)−0.0036 (4)−0.0033 (4)
C20.0300 (5)0.0200 (5)0.0266 (6)−0.0080 (4)−0.0036 (4)−0.0009 (4)
C30.0291 (5)0.0180 (5)0.0315 (6)−0.0062 (4)−0.0065 (4)−0.0058 (4)
C40.0258 (5)0.0209 (5)0.0252 (6)−0.0040 (4)−0.0051 (4)−0.0084 (4)
C50.0207 (5)0.0183 (5)0.0203 (5)−0.0048 (4)−0.0036 (4)−0.0032 (4)
C60.0200 (4)0.0173 (4)0.0211 (5)−0.0030 (4)−0.0041 (4)−0.0043 (4)
C70.0226 (5)0.0164 (4)0.0220 (5)−0.0038 (4)−0.0032 (4)−0.0038 (4)
C80.0285 (5)0.0184 (5)0.0205 (5)−0.0052 (4)−0.0037 (4)−0.0035 (4)
C90.0214 (5)0.0184 (5)0.0198 (5)−0.0023 (4)−0.0028 (4)−0.0048 (4)
C100.0214 (5)0.0179 (5)0.0197 (5)−0.0018 (4)−0.0027 (4)−0.0051 (4)
C110.0267 (5)0.0193 (5)0.0193 (5)−0.0054 (4)−0.0006 (4)−0.0035 (4)
C120.0274 (5)0.0218 (5)0.0239 (6)−0.0078 (4)−0.0007 (4)−0.0074 (4)
C130.0209 (5)0.0234 (5)0.0197 (5)−0.0022 (4)−0.0028 (4)−0.0073 (4)
C140.0279 (5)0.0222 (5)0.0194 (5)−0.0076 (4)0.0000 (4)−0.0036 (4)
C150.0276 (5)0.0201 (5)0.0220 (5)−0.0073 (4)−0.0013 (4)−0.0051 (4)
C160.0236 (5)0.0263 (5)0.0168 (5)−0.0056 (4)−0.0002 (4)−0.0047 (4)
C170.0227 (5)0.0238 (5)0.0205 (5)−0.0028 (4)−0.0022 (4)−0.0064 (4)
C180.0241 (5)0.0233 (5)0.0198 (5)−0.0029 (4)−0.0039 (4)−0.0044 (4)
C190.0287 (5)0.0251 (5)0.0192 (5)−0.0080 (4)−0.0010 (4)−0.0052 (4)
C200.0303 (6)0.0317 (6)0.0202 (5)−0.0099 (5)−0.0004 (4)−0.0049 (4)
C210.0431 (7)0.0501 (8)0.0255 (6)−0.0195 (6)0.0053 (5)−0.0180 (6)
Geometric parameters (Å, º) top
O1—C91.2382 (13)C12—C131.3976 (15)
O2—C51.3534 (13)C12—H12A0.9300
O2—H1O20.94 (2)C13—C141.3967 (15)
O3—C131.3477 (13)C14—C151.3922 (15)
O3—C161.4416 (13)C14—H14A0.9300
C1—C21.3844 (15)C15—H15A0.9300
C1—C61.3978 (15)C16—C171.5106 (15)
C1—H1A0.9300C16—H16A0.9700
C2—C31.3891 (17)C16—H16B0.9700
C2—H2A0.9300C17—C181.5189 (16)
C3—C41.3856 (16)C17—H17A0.9700
C3—H3A0.9300C17—H17B0.9700
C4—C51.3951 (14)C18—C191.5263 (15)
C4—H4A0.9300C18—H18A0.9700
C5—C61.4086 (15)C18—H18B0.9700
C6—C71.4587 (14)C19—C201.5181 (16)
C7—C81.3424 (15)C19—H19A0.9700
C7—H7A0.9300C19—H19B0.9700
C8—C91.4738 (14)C20—C211.5247 (17)
C8—H8A0.9300C20—H20A0.9700
C9—C101.4815 (15)C20—H20B0.9700
C10—C151.3953 (15)C21—H21A0.9600
C10—C111.4064 (14)C21—H21B0.9600
C11—C121.3763 (15)C21—H21C0.9600
C11—H11A0.9300
C5—O2—H1O2113.6 (11)C15—C14—H14A120.4
C13—O3—C16119.91 (8)C13—C14—H14A120.4
C2—C1—C6121.38 (11)C14—C15—C10121.74 (10)
C2—C1—H1A119.3C14—C15—H15A119.1
C6—C1—H1A119.3C10—C15—H15A119.1
C1—C2—C3119.72 (10)O3—C16—C17105.61 (9)
C1—C2—H2A120.1O3—C16—H16A110.6
C3—C2—H2A120.1C17—C16—H16A110.6
C4—C3—C2120.39 (10)O3—C16—H16B110.6
C4—C3—H3A119.8C17—C16—H16B110.6
C2—C3—H3A119.8H16A—C16—H16B108.7
C3—C4—C5119.82 (10)C16—C17—C18113.53 (9)
C3—C4—H4A120.1C16—C17—H17A108.9
C5—C4—H4A120.1C18—C17—H17A108.9
O2—C5—C4122.26 (10)C16—C17—H17B108.9
O2—C5—C6117.18 (9)C18—C17—H17B108.9
C4—C5—C6120.56 (10)H17A—C17—H17B107.7
C1—C6—C5118.05 (9)C17—C18—C19111.28 (9)
C1—C6—C7123.26 (10)C17—C18—H18A109.4
C5—C6—C7118.68 (9)C19—C18—H18A109.4
C8—C7—C6126.09 (10)C17—C18—H18B109.4
C8—C7—H7A117.0C19—C18—H18B109.4
C6—C7—H7A117.0H18A—C18—H18B108.0
C7—C8—C9122.19 (10)C20—C19—C18114.28 (9)
C7—C8—H8A118.9C20—C19—H19A108.7
C9—C8—H8A118.9C18—C19—H19A108.7
O1—C9—C8121.95 (10)C20—C19—H19B108.7
O1—C9—C10119.27 (9)C18—C19—H19B108.7
C8—C9—C10118.76 (9)H19A—C19—H19B107.6
C15—C10—C11117.94 (10)C19—C20—C21112.35 (10)
C15—C10—C9123.98 (9)C19—C20—H20A109.1
C11—C10—C9118.07 (9)C21—C20—H20A109.1
C12—C11—C10120.94 (10)C19—C20—H20B109.1
C12—C11—H11A119.5C21—C20—H20B109.1
C10—C11—H11A119.5H20A—C20—H20B107.9
C11—C12—C13120.47 (10)C20—C21—H21A109.5
C11—C12—H12A119.8C20—C21—H21B109.5
C13—C12—H12A119.8H21A—C21—H21B109.5
O3—C13—C14125.30 (10)C20—C21—H21C109.5
O3—C13—C12115.01 (9)H21A—C21—H21C109.5
C14—C13—C12119.69 (10)H21B—C21—H21C109.5
C15—C14—C13119.22 (10)
C6—C1—C2—C3−0.37 (17)C8—C9—C10—C11−171.57 (9)
C1—C2—C3—C41.75 (17)C15—C10—C11—C12−0.18 (16)
C2—C3—C4—C5−0.56 (16)C9—C10—C11—C12179.21 (9)
C3—C4—C5—O2177.95 (9)C10—C11—C12—C130.31 (17)
C3—C4—C5—C6−2.02 (16)C16—O3—C13—C142.51 (16)
C2—C1—C6—C5−2.13 (16)C16—O3—C13—C12−178.00 (9)
C2—C1—C6—C7177.29 (10)C11—C12—C13—O3−179.89 (9)
O2—C5—C6—C1−176.65 (9)C11—C12—C13—C14−0.37 (16)
C4—C5—C6—C13.32 (15)O3—C13—C14—C15179.78 (10)
O2—C5—C6—C73.90 (14)C12—C13—C14—C150.31 (16)
C4—C5—C6—C7−176.13 (9)C13—C14—C15—C10−0.19 (17)
C1—C6—C7—C8−7.76 (17)C11—C10—C15—C140.12 (16)
C5—C6—C7—C8171.66 (10)C9—C10—C15—C14−179.23 (10)
C6—C7—C8—C9−176.61 (9)C13—O3—C16—C17166.42 (9)
C7—C8—C9—O10.88 (17)O3—C16—C17—C18−178.07 (8)
C7—C8—C9—C10179.45 (10)C16—C17—C18—C19173.51 (9)
O1—C9—C10—C15−173.62 (10)C17—C18—C19—C20179.26 (9)
C8—C9—C10—C157.77 (15)C18—C19—C20—C21177.93 (10)
O1—C9—C10—C117.04 (15)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C1–C6 ring.
D—H···AD—HH···AD···AD—H···A
O2—H1O2···O1i0.94 (2)1.78 (2)2.6862 (15)163.3 (19)
C7—H7A···O2i0.932.373.2526 (18)158
C16—H16A···Cg1ii0.972.913.6117 (16)130
Symmetry codes: (i) −x, −y+2, −z+2; (ii) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formulaC21H24O3
Mr324.40
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)7.485 (2), 10.834 (3), 11.673 (3)
α, β, γ (°)73.858 (5), 77.961 (6), 76.941 (6)
V (Å3)874.9 (4)
Z2
Radiation typeMo Kα
µ (mm−1)0.08
Crystal size (mm)0.47 × 0.14 × 0.12
Data collection
DiffractometerBruker APEX DUO CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.963, 0.991
No. of measured, independent and
observed [I > 2σ(I)] reflections		17565, 4576, 3781
Rint0.026
(sin θ/λ)max (Å−1)0.682
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.133, 1.02
No. of reflections4576
No. of parameters222
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.39, −0.23

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the C1–C6 ring.
D—H···AD—HH···AD···AD—H···A
O2—H1O2···O1i0.94 (2)1.78 (2)2.6862 (15)163.3 (19)
C7—H7A···O2i0.932.373.2526 (18)158
C16—H16A···Cg1ii0.972.913.6117 (16)130
Symmetry codes: (i) −x, −y+2, −z+2; (ii) −x+1, −y+2, −z+1.
 

Footnotes

‡Thomson Reuters ResearcherID: A-5599-2009.

Acknowledgements

IAR and SIJA thank the Malaysian Government and Universiti Sains Malaysia for the Fundamental Research Grant Scheme (FRGS) No. 203/PFIZIK/6711171. ZN and HH thank Universiti Malaysia Sarawak and the Ministry of Science, Technology and Innovation (MOSTI), for financing this project through FRGS/01(14)/743/2010 (29). SMHF thank the Malaysian Government and Universiti Malaysia Sarawak for providing a schol­arship for postgraduate studies.

References

First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science Google Scholar
 First citationBruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationCosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107.  CrossRef CAS Web of Science IUCr Journals Google Scholar
 First citationNgaini, Z., Fadzillah, S. M. H., Hussain, H., Razak, I. A. & Fun, H.-K. (2010). Acta Cryst. E66, o3275–o3276.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationNgaini, Z., Fadzillah, S. M. H., Hussain, H., Razak, I. A. & Fun, H.-K. (2011). Acta Cryst. E67, o169–o170.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationRazak, I. A., Fun, H.-K., Ngaini, Z., Rahman, N. I. A. & Hussain, H. (2009). Acta Cryst. E65, o1439–o1440.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 10| October 2012| Page o2909
https://doi.org/10.1107/S1600536812038007
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS