(2E)-1-(2,4-Dichloro­phen­yl)-3-(3,4,5-trimeth­oxy­phen­yl)prop-2-en-1-one

Fun, H.-K.; Chia, T.S.; Sapnakumari, M.; Narayana, B.; Sarojini, B.K.

doi:10.1107/S1600536812016339

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1465

doi:10.1107/S1600536812016339

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(2E)-1-(2,4-Dichlorophenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one

Hoong-Kun Fun,^a ^*‡ Tze Shyang Chia,^a M. Sapnakumari,^b B. Narayana ^b and B. K. Sarojini ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and ^cDepartment of Chemistry, P. A. College of Engineering, Nadupadavu, Mangalore 574 153, India
^*Correspondence e-mail: hkfun@usm.my

(Received 15 April 2012; accepted 15 April 2012; online 21 April 2012)

In the title compound, C₁₈H₁₆Cl₂O₄, the dihedral angle between the benzene rings is 82.40 (4)°. The methoxy groups at both meta positions of the 3,4,5-trimethoxyphenyl ring are slightly twisted from the aromatic ring [C—O—C—C = −166.60 (8) and −6.18 (13)°], whereas the methoxy group at the para position is almost perpendicular [C—O—C—C = 112.08 (9)°]. The ketone O atom is connected to the 2,4-dichlorophenyl group through a C_ar—C_ar—C—O (ar = aromatic) torsion angle of −116.43 (9)°. In the crystal, molecules are linked by C—H⋯O hydrogen bonds into infinite chains along the b axis. The crystal structure also features C—H⋯π interactions.

Related literature

For a related structure, see: Fun et al. (2012 ). For background to various chalcone derivatives, see: Samshuddin et al. (2011 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ).

Experimental

Crystal data

C₁₈H₁₆Cl₂O₄
M_r = 367.21
Orthorhombic, P b c a
a = 9.4305 (5) Å
b = 13.9334 (8) Å
c = 25.6417 (14) Å
V = 3369.3 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.40 mm⁻¹
T = 100 K
0.48 × 0.39 × 0.22 mm

Data collection

Bruker APEX DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.829, T_max = 0.917
24763 measured reflections
6139 independent reflections
5445 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.086
S = 1.03
6139 reflections
220 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.22 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
C9—H9A⋯O3ⁱ	0.93	2.53	3.3442 (11)	147
C17—H17A⋯Cg1ⁱⁱ	0.96	2.60	3.2965 (11)	130
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) $[-x, y+{\script{3\over 2}}, -z+{\script{3\over 2}}]$ .

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

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812016339/hb6742sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812016339/hb6742Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812016339/hb6742Isup3.cml

checkCIF report

Comment top

In continuation of our work on the synthesis of chalcones (Fun et al., 2012, Samshuddin et al., 2011) as potential precursors for biodynamic functionalized derivatives, the title compound was prepared and its crystal structure is now reported.

In the title compound (Fig. 1), the dihedral angle between the two benzene rings (C1–C6 & C10–C15) is 82.40 (4)°. The two methoxy groups at both meta positions (at atoms C12 & C14) are slightly twisted from the attached benzene ring with torsion angles C16—O1—C12—C13 = -166.60 (8)° and C18—O3—C14—C15 = -6.18 (13)°, whereas the methoxy group at para position (at atom C13) is almost perpendicular with C17—O2—C13—C14 = 112.08 (9)°. The atom O4 is connected to 2,4-dichlorophenyl group (Cl1/Cl2/C1–C6) through torsion angle [C5—C6—C7—O4] of -116.43 (9)°. Bond lengths and angles are comparable to a related structure (Fun et al., 2012).

In the crystal (Fig. 2), molecules are linked by C9—H9A—O3 hydrogen bonds into infinite chains along the b axis. The crystal is further stabilized by C—H···π interactions (Table 1), involving Cg1 which is the centroid of C10—C15 ring.

Related literature top

For a related structure, see: Fun et al. (2012). For background to various chalcone derivatives, see: Samshuddin et al. (2011). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental top

To a mixture of 2,4-dichloroacetophenone (1.89 g, 0.01 mol) and 3,4,5-trimethoxybenzaldehyde (1.96 g, 0.01 mol) in ethanol (50 ml), 15 ml of 10% sodium hydroxide solution was added and stirred at 0–5 °C for 1 h. The precipitate formed was collected by filtration and purified by recrystallization from ethanol. Colourless blocks were grown from toluene as solvent by slow evaporation method (M.P.: 335–337 K).

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

	Fig. 1. The molecular structure of the title compound with 50% probability displacement ellipsoids.
	Fig. 2. The crystal packing of the title compound. The dashed lines represent the hydrogen bonds.

(2E)-1-(2,4-Dichlorophenyl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one top

Crystal data top

C₁₈H₁₆Cl₂O₄	F(000) = 1520
M_r = 367.21	D_x = 1.448 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 9912 reflections
a = 9.4305 (5) Å	θ = 2.7–32.7°
b = 13.9334 (8) Å	µ = 0.40 mm⁻¹
c = 25.6417 (14) Å	T = 100 K
V = 3369.3 (3) Å³	Block, colourless
Z = 8	0.48 × 0.39 × 0.22 mm

Data collection top

Bruker APEX DUO CCD diffractometer	6139 independent reflections
Radiation source: fine-focus sealed tube	5445 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ϕ and ω scans	θ_max = 32.7°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→14
T_min = 0.829, T_max = 0.917	k = −20→21
24763 measured reflections	l = −38→35

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.086	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0458P)² + 1.108P] where P = (F_o² + 2F_c²)/3
6139 reflections	(Δ/σ)_max = 0.002
220 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₈H₁₆Cl₂O₄	V = 3369.3 (3) Å³
M_r = 367.21	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 9.4305 (5) Å	µ = 0.40 mm⁻¹
b = 13.9334 (8) Å	T = 100 K
c = 25.6417 (14) Å	0.48 × 0.39 × 0.22 mm

Data collection top

Bruker APEX DUO CCD diffractometer	6139 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	5445 reflections with I > 2σ(I)
T_min = 0.829, T_max = 0.917	R_int = 0.020
24763 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.086	H-atom parameters constrained
S = 1.03	Δρ_max = 0.52 e Å⁻³
6139 reflections	Δρ_min = −0.22 e Å⁻³
220 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 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
Cl1	0.28135 (3)	0.217251 (16)	0.611803 (9)	0.02108 (6)
Cl2	0.68551 (3)	0.053651 (17)	0.730224 (9)	0.02548 (6)
O1	0.85362 (8)	0.59918 (5)	0.48151 (3)	0.02017 (13)
O2	0.81150 (7)	0.78269 (5)	0.51372 (3)	0.01807 (13)
O3	0.67985 (7)	0.82227 (5)	0.60144 (3)	0.01813 (13)
O4	0.22886 (7)	0.40914 (5)	0.67797 (3)	0.01916 (13)
C1	0.41001 (9)	0.22749 (6)	0.65990 (3)	0.01458 (14)
C2	0.48428 (10)	0.14561 (6)	0.67434 (3)	0.01770 (15)
H2A	0.4638	0.0865	0.6593	0.021*
C3	0.58992 (10)	0.15424 (6)	0.71183 (3)	0.01775 (16)
C4	0.62109 (11)	0.24156 (7)	0.73518 (4)	0.02006 (17)
H4A	0.6907	0.2458	0.7608	0.024*
C5	0.54655 (10)	0.32244 (6)	0.71967 (3)	0.01803 (16)
H5A	0.5680	0.3815	0.7346	0.022*
C6	0.43967 (9)	0.31692 (6)	0.68200 (3)	0.01377 (14)
C7	0.35648 (9)	0.40595 (6)	0.66920 (3)	0.01436 (14)
C8	0.43334 (9)	0.48838 (6)	0.64771 (3)	0.01531 (14)
H8A	0.3917	0.5488	0.6498	0.018*
C9	0.56145 (9)	0.48055 (6)	0.62511 (3)	0.01455 (14)
H9A	0.6055	0.4208	0.6259	0.017*
C10	0.63649 (9)	0.55929 (6)	0.59932 (3)	0.01371 (14)
C11	0.72028 (9)	0.53747 (6)	0.55583 (3)	0.01506 (14)
H11A	0.7355	0.4739	0.5462	0.018*
C12	0.78076 (9)	0.61202 (6)	0.52700 (3)	0.01442 (14)
C13	0.76521 (9)	0.70727 (6)	0.54348 (3)	0.01393 (14)
C14	0.68727 (9)	0.72740 (6)	0.58881 (3)	0.01376 (14)
C15	0.62042 (9)	0.65414 (6)	0.61624 (3)	0.01450 (14)
H15A	0.5657	0.6680	0.6455	0.017*
C16	0.84445 (12)	0.50620 (8)	0.45782 (4)	0.02523 (19)
H16A	0.8912	0.5074	0.4246	0.038*
H16B	0.7466	0.4893	0.4531	0.038*
H16C	0.8894	0.4597	0.4799	0.038*
C17	0.96130 (10)	0.79619 (7)	0.51322 (4)	0.02343 (18)
H17A	0.9849	0.8475	0.4898	0.035*
H17B	1.0066	0.7382	0.5018	0.035*
H17C	0.9933	0.8119	0.5477	0.035*
C18	0.58610 (11)	0.84829 (7)	0.64272 (4)	0.0248 (2)
H18A	0.5853	0.9168	0.6465	0.037*
H18B	0.6178	0.8194	0.6746	0.037*
H18C	0.4921	0.8262	0.6348	0.037*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.02216 (11)	0.01837 (10)	0.02271 (10)	−0.00144 (8)	−0.00764 (8)	−0.00429 (7)
Cl2	0.03293 (13)	0.02033 (11)	0.02319 (11)	0.00754 (9)	−0.00281 (9)	0.00501 (8)
O1	0.0237 (3)	0.0184 (3)	0.0184 (3)	−0.0001 (3)	0.0076 (2)	−0.0007 (2)
O2	0.0143 (3)	0.0170 (3)	0.0229 (3)	−0.0021 (2)	0.0016 (2)	0.0081 (2)
O3	0.0185 (3)	0.0108 (3)	0.0251 (3)	−0.0023 (2)	0.0047 (2)	−0.0020 (2)
O4	0.0144 (3)	0.0186 (3)	0.0245 (3)	−0.0026 (2)	0.0027 (2)	−0.0016 (2)
C1	0.0158 (3)	0.0142 (3)	0.0137 (3)	−0.0028 (3)	−0.0004 (3)	−0.0005 (3)
C2	0.0225 (4)	0.0133 (3)	0.0173 (3)	−0.0006 (3)	0.0001 (3)	−0.0006 (3)
C3	0.0217 (4)	0.0151 (3)	0.0164 (3)	0.0015 (3)	0.0003 (3)	0.0035 (3)
C4	0.0227 (4)	0.0185 (4)	0.0190 (4)	−0.0014 (3)	−0.0058 (3)	0.0018 (3)
C5	0.0210 (4)	0.0147 (3)	0.0184 (4)	−0.0036 (3)	−0.0036 (3)	0.0000 (3)
C6	0.0148 (3)	0.0122 (3)	0.0143 (3)	−0.0027 (3)	0.0010 (3)	0.0011 (2)
C7	0.0153 (3)	0.0132 (3)	0.0146 (3)	−0.0027 (3)	0.0003 (3)	−0.0011 (3)
C8	0.0148 (3)	0.0118 (3)	0.0193 (4)	−0.0006 (3)	0.0017 (3)	0.0018 (3)
C9	0.0148 (3)	0.0122 (3)	0.0167 (3)	−0.0004 (3)	0.0006 (3)	0.0019 (3)
C10	0.0127 (3)	0.0117 (3)	0.0168 (3)	0.0002 (3)	0.0008 (3)	0.0024 (3)
C11	0.0144 (3)	0.0128 (3)	0.0180 (3)	0.0016 (3)	0.0017 (3)	0.0017 (3)
C12	0.0130 (3)	0.0151 (3)	0.0152 (3)	0.0013 (3)	0.0017 (3)	0.0017 (3)
C13	0.0117 (3)	0.0133 (3)	0.0168 (3)	−0.0003 (3)	0.0006 (3)	0.0035 (3)
C14	0.0120 (3)	0.0111 (3)	0.0182 (3)	−0.0006 (3)	−0.0002 (3)	0.0003 (3)
C15	0.0138 (3)	0.0127 (3)	0.0170 (3)	−0.0009 (3)	0.0023 (3)	0.0006 (3)
C16	0.0312 (5)	0.0230 (4)	0.0216 (4)	−0.0004 (4)	0.0065 (4)	−0.0058 (3)
C17	0.0156 (4)	0.0213 (4)	0.0334 (5)	−0.0034 (3)	0.0058 (3)	0.0033 (4)
C18	0.0246 (5)	0.0164 (4)	0.0334 (5)	−0.0007 (3)	0.0092 (4)	−0.0067 (3)

Geometric parameters (Å, º) top

Cl1—C1	1.7360 (9)	C8—H8A	0.9300
Cl2—C3	1.7319 (9)	C9—C10	1.4635 (11)
O1—C12	1.3655 (10)	C9—H9A	0.9300
O1—C16	1.4334 (12)	C10—C15	1.3992 (11)
O2—C13	1.3702 (10)	C10—C11	1.4000 (12)
O2—C17	1.4252 (11)	C11—C12	1.3967 (12)
O3—C14	1.3628 (10)	C11—H11A	0.9300
O3—C18	1.4260 (12)	C12—C13	1.4005 (12)
O4—C7	1.2252 (11)	C13—C14	1.4034 (12)
C1—C2	1.3890 (12)	C14—C15	1.3909 (11)
C1—C6	1.3971 (11)	C15—H15A	0.9300
C2—C3	1.3896 (13)	C16—H16A	0.9600
C2—H2A	0.9300	C16—H16B	0.9600
C3—C4	1.3874 (13)	C16—H16C	0.9600
C4—C5	1.3864 (13)	C17—H17A	0.9600
C4—H4A	0.9300	C17—H17B	0.9600
C5—C6	1.3983 (12)	C17—H17C	0.9600
C5—H5A	0.9300	C18—H18A	0.9600
C6—C7	1.5040 (12)	C18—H18B	0.9600
C7—C8	1.4658 (12)	C18—H18C	0.9600
C8—C9	1.3444 (12)

C12—O1—C16	116.75 (7)	C12—C11—C10	119.38 (8)
C13—O2—C17	114.96 (7)	C12—C11—H11A	120.3
C14—O3—C18	117.06 (7)	C10—C11—H11A	120.3
C2—C1—C6	121.57 (8)	O1—C12—C11	124.07 (8)
C2—C1—Cl1	118.31 (6)	O1—C12—C13	115.76 (7)
C6—C1—Cl1	120.09 (6)	C11—C12—C13	120.15 (8)
C1—C2—C3	118.35 (8)	O2—C13—C12	121.69 (8)
C1—C2—H2A	120.8	O2—C13—C14	118.34 (7)
C3—C2—H2A	120.8	C12—C13—C14	119.62 (7)
C4—C3—C2	121.75 (8)	O3—C14—C15	124.64 (8)
C4—C3—Cl2	118.81 (7)	O3—C14—C13	114.69 (7)
C2—C3—Cl2	119.44 (7)	C15—C14—C13	120.63 (8)
C5—C4—C3	118.79 (8)	C14—C15—C10	119.16 (8)
C5—C4—H4A	120.6	C14—C15—H15A	120.4
C3—C4—H4A	120.6	C10—C15—H15A	120.4
C4—C5—C6	121.26 (8)	O1—C16—H16A	109.5
C4—C5—H5A	119.4	O1—C16—H16B	109.5
C6—C5—H5A	119.4	H16A—C16—H16B	109.5
C1—C6—C5	118.26 (8)	O1—C16—H16C	109.5
C1—C6—C7	122.87 (7)	H16A—C16—H16C	109.5
C5—C6—C7	118.78 (7)	H16B—C16—H16C	109.5
O4—C7—C8	121.76 (8)	O2—C17—H17A	109.5
O4—C7—C6	120.16 (8)	O2—C17—H17B	109.5
C8—C7—C6	118.06 (7)	H17A—C17—H17B	109.5
C9—C8—C7	122.88 (8)	O2—C17—H17C	109.5
C9—C8—H8A	118.6	H17A—C17—H17C	109.5
C7—C8—H8A	118.6	H17B—C17—H17C	109.5
C8—C9—C10	124.64 (8)	O3—C18—H18A	109.5
C8—C9—H9A	117.7	O3—C18—H18B	109.5
C10—C9—H9A	117.7	H18A—C18—H18B	109.5
C15—C10—C11	120.88 (7)	O3—C18—H18C	109.5
C15—C10—C9	121.04 (7)	H18A—C18—H18C	109.5
C11—C10—C9	118.03 (7)	H18B—C18—H18C	109.5

C6—C1—C2—C3	0.19 (13)	C15—C10—C11—C12	−4.30 (13)
Cl1—C1—C2—C3	178.29 (7)	C9—C10—C11—C12	173.10 (8)
C1—C2—C3—C4	0.71 (14)	C16—O1—C12—C11	11.64 (13)
C1—C2—C3—Cl2	−179.40 (7)	C16—O1—C12—C13	−166.60 (8)
C2—C3—C4—C5	−1.43 (14)	C10—C11—C12—O1	−174.04 (8)
Cl2—C3—C4—C5	178.69 (7)	C10—C11—C12—C13	4.13 (13)
C3—C4—C5—C6	1.26 (14)	C17—O2—C13—C12	−74.72 (11)
C2—C1—C6—C5	−0.34 (13)	C17—O2—C13—C14	112.08 (9)
Cl1—C1—C6—C5	−178.41 (7)	O1—C12—C13—O2	4.53 (12)
C2—C1—C6—C7	−176.86 (8)	C11—C12—C13—O2	−173.79 (8)
Cl1—C1—C6—C7	5.07 (11)	O1—C12—C13—C14	177.64 (8)
C4—C5—C6—C1	−0.39 (13)	C11—C12—C13—C14	−0.67 (13)
C4—C5—C6—C7	176.27 (8)	C18—O3—C14—C15	−6.18 (13)
C1—C6—C7—O4	60.07 (12)	C18—O3—C14—C13	171.48 (8)
C5—C6—C7—O4	−116.43 (9)	O2—C13—C14—O3	−7.14 (11)
C1—C6—C7—C8	−121.77 (9)	C12—C13—C14—O3	179.52 (8)
C5—C6—C7—C8	61.73 (11)	O2—C13—C14—C15	170.62 (8)
O4—C7—C8—C9	−162.01 (9)	C12—C13—C14—C15	−2.72 (13)
C6—C7—C8—C9	19.86 (12)	O3—C14—C15—C10	−179.90 (8)
C7—C8—C9—C10	174.62 (8)	C13—C14—C15—C10	2.57 (13)
C8—C9—C10—C15	31.54 (13)	C11—C10—C15—C14	0.95 (13)
C8—C9—C10—C11	−145.86 (9)	C9—C10—C15—C14	−176.36 (8)

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
C9—H9A···O3ⁱ	0.93	2.53	3.3442 (11)	147
C17—H17A···Cg1ⁱⁱ	0.96	2.60	3.2965 (11)	130

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₆Cl₂O₄
M_r	367.21
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	100
a, b, c (Å)	9.4305 (5), 13.9334 (8), 25.6417 (14)
V (Å³)	3369.3 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.40
Crystal size (mm)	0.48 × 0.39 × 0.22

Data collection
Diffractometer	Bruker APEX DUO CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.829, 0.917
No. of measured, independent and observed [I > 2σ(I)] reflections	24763, 6139, 5445
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.759

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.086, 1.03
No. of reflections	6139
No. of parameters	220
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.22

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 C10—C15 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O3ⁱ	0.93	2.53	3.3442 (11)	147
C17—H17A···Cg1ⁱⁱ	0.96	2.60	3.2965 (11)	130

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

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

HKF and TSC thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSC also thanks the Malaysian Government and USM for the award of a research fellowship. BN thanks the UGC, New Delhi, Government of India, for the purchase of chemicals through the SAP–DRS–Phase 1 programme.

References

Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Fun, H.-K., Chia, T. S., Sapnakumari, M., Narayana, B. & Sarojini, B. K. (2012). Acta Cryst. E68, o629. CSD CrossRef IUCr Journals Google Scholar
Samshuddin, S., Narayana, B., Shetty, D. N. & Raghavendra, R. (2011). Der Pharma Chem. 3, 232–240. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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