(1E,4E)-1,5-Bis(4-methyl­phen­yl)penta-1,4-dien-3-one

Arshad, M.N.; Tahir, M.N.; Asghar, M.N.; Khan, I.U.; Ashfaq, M.

doi:10.1107/S1600536808020084

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1413

doi:10.1107/S1600536808020084

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(1E,4E)-1,5-Bis(4-methylphenyl)penta-1,4-dien-3-one

Muhammad Nadeem Arshad,^a Muhammad Nawaz Tahir,^b ^* Muhammad Nadeem Asghar,^a Islam Ullah Khan ^a and Muhammad Ashfaq ^a

^aGovernment College University, Department of Chemistry, Lahore, Pakistan, and ^bUniversity of Sargodha, Department of Physics, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 18 June 2008; accepted 1 July 2008; online 5 July 2008)

The title compound, C₁₉H₁₈O, crystallizes in a non-centrosymmetric space group although the molecule has no chiral centre. The dihedral angle between the aromatic rings is 20.43 (13)°. The structure is stabilized by two intramolecular hydrogen bonds, and by four π–π and three C—H⋯π interactions between the aromatic rings. The perpendicular distances between the centroids of the rings involved in the π–π interactions have values of 1.996, 2.061, 2.181 and 2.189 Å.

Related literature

For related literature, see: Butcher et al. (2006 ); Conard & Dolliver (1943 ); Harrison et al. (2006 ).

Experimental

Crystal data

C₁₉H₁₈O
M_r = 262.33
Monoclinic, C 2
a = 19.937 (2) Å
b = 5.8637 (5) Å
c = 14.9207 (14) Å
β = 121.001 (3)°
V = 1495.1 (2) Å³
Z = 4
Mo Kα radiation radiation
μ = 0.07 mm⁻¹
T = 296 (2) K
0.25 × 0.20 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.980, T_max = 0.988
9611 measured reflections
2288 independent reflections
1800 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.137
S = 1.04
2288 reflections
183 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

CgA and CgB are the centroids of the C4–C9 and C13–C18 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1	0.93	2.49	2.817 (4)	101
C12—H12⋯O1	0.93	2.48	2.819 (3)	102
C5—H5⋯CgAⁱ	0.93	2.82	3.523 (3)	133
C9—H9⋯CgBⁱⁱ	0.93	2.89	3.604 (3)	134
C18—H18⋯CgBⁱⁱⁱ	0.93	2.95	3.621 (3)	131
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z]$ ; (ii) -x+1, y, -z+1; (iii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+1]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: APEX2; 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: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2003 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808020084/bq2087sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808020084/bq2087Isup2.hkl

checkCIF report

Comment top

The chalcones are being synthesized since long for various applications. The title compound (I) differs from 1,5-Bis(4-methoxyphenyl)penta-1,4- dien-3-one (II) (Harrison et al., 2006) and 1,5-Bis(4-chlorophenyl)penta-1,4- dien-3-one (III) (Butcher et al., 2006) due the attachement of methyl group at para position instead of methoxy or chloro moieties. The authors have reported their nonlinear optical (NLO) activity as the compounds crystallize in non-centrosymmetric space groups. The title compound have a monoclinic crystal system and a non-centrosymmetric space group C2. Therefore, it is assumed that this compound will also have nonlinear optical activity.

We compare the bond distances and bond angles realised in (I) with the corresponding values observed in (II) and (III). The central portion of (I) shows double and single bonds originating from O1-atom and five-C-atom behave like a backbone. In (I), the bond distance O1==C1 is 1.211 (4) Å, greater than 1.170 (12) Å (III) but shorter than 1.230 (6) Å as in (II). The bond distances C1—C2 = 1.480 (3) Å, C2==C3 = 1.329 (3) Å, C3—C4 = 1.465 (3) Å are observed in (I), in (II) and (III) the corresponding values are [1.476 (4), 1.318 (5), 1.475 (4) Å] and [1.579 (10), 1.239 (7), 1.502 (7) Å], respectively. The range of bond angles for backbone C-atoms in (I) is 116.0 (2)°-127.8 (2)°, whereas in (II) and (III), the range is 123.8 (5)°- 126.4 (4)° and 103.1 (9)°-128.5 (4)°, respectively. The dihedral angle between the aromatic rings A (C4—C9) and B (C13—C18) is 20.27 (13)°, which is less than 56.92 (9)° and 53.4 (5) as reported in (II) and (III), respectively. The title compound is stabilized due to two intramolecular H-bonding (Fig 1) and three C—H···π interactions as given in Table 1. There exist also π–π-interactions between the aromatic rings. The perpendicular distance between the centroids CgA and CgB [(CgA···CgA^iv), symmetry code: iv = -x + 1/2, y - 1/2, -z], [(CgA···CgB^v), symmetry code: v = -x + 1, y + 1, -z + 1], [(CgB···CgAⁱⁱ), symmetry code: ii = -x + 1, y, -z + 1] and [(CgB···CgB^vi), symmetry code: vi = -x + 3/2, y - 1/2, -z + 1] have values of 1.996, 2.181, 2.061 and 2.189 Å, respectively.

Related literature top

For related literature, see: Butcher et al. (2006); Conard & Dolliver (1943); Harrison et al. (2006). [CgA and CgB are the centroids of the C4–C9 and C13–C18 rings, respectively.]

Experimental top

The title compound (I) was synthesized using the method of Conard & Dolliver, 1943. Sodium hydroxide (0.8 g, 0.0208 mmol) was dissolved in distilled water (10 ml) and ethanol (8 ml) in a round bottom flask. The solution was cooled to room temperature. Half of the mixture of p-tolualdehide (1 g, 0.00833 mmol) and acetone (0.24 g, 0.00417 mmol) added to the above solution and stirred at room temperature for 15 minute then the remaining mixture was added and stirred for 2 h under the same conditions. Yellow precipitate obtained was filtered and washed with cold water. The washed precipitate was crystallized in aceton under slow evaporation.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 (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: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Figures top

	Fig. 1. ORTEP drawing of the title compound, with the atom numbering scheme. The thermal ellipsoids are drawn at the 50% probability level. H-atoms are shown by small circles of arbitrary radii. The intramolecular H-bonding is shown by dotted lines.
	Fig. 2. The packing figure (PLATON: Spek, 2003) which shows the stacking of molecules in a unit cell.

(1E,4E)-1,5-Bis(4-methylphenyl)penta-1,4-dien-3-one top

Crystal data top

C₁₉H₁₈O	F(000) = 560
M_r = 262.33	D_x = 1.165 Mg m⁻³
Monoclinic, C2	Mo Kα radiation radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 3173 reflections
a = 19.937 (2) Å	θ = 2.1–29.6°
b = 5.8637 (5) Å	µ = 0.07 mm⁻¹
c = 14.9207 (14) Å	T = 296 K
β = 121.001 (3)°	Prism, yellow
V = 1495.1 (2) Å³	0.25 × 0.20 × 0.15 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	2288 independent reflections
Radiation source: fine-focus sealed tube	1800 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
Detector resolution: 7.40 pixels mm^-1	θ_max = 29.6°, θ_min = 2.1°
ω scans	h = −26→27
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −8→4
T_min = 0.980, T_max = 0.988	l = −20→18
9611 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)] = 0.048	H-atom parameters constrained
wR(F²) = 0.137	w = 1/[σ²(F_o²) + (0.0717P)² + 0.4143P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2288 reflections	Δρ_max = 0.22 e Å⁻³
183 parameters	Δρ_min = −0.21 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 726 Friedel pairs
Primary atom site location: structure-invariant direct methods

Crystal data top

C₁₉H₁₈O	V = 1495.1 (2) Å³
M_r = 262.33	Z = 4
Monoclinic, C2	Mo Kα radiation
a = 19.937 (2) Å	µ = 0.07 mm⁻¹
b = 5.8637 (5) Å	T = 296 K
c = 14.9207 (14) Å	0.25 × 0.20 × 0.15 mm
β = 121.001 (3)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	2288 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1800 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.988	R_int = 0.024
9611 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	1 restraint
wR(F²) = 0.137	H-atom parameters constrained
S = 1.04	Δρ_max = 0.22 e Å⁻³
2288 reflections	Δρ_min = −0.21 e Å⁻³
183 parameters	Absolute structure: Flack (1983), 726 Friedel pairs

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	0.49937 (12)	1.0189 (4)	0.63720 (18)	0.0745 (7)
C1	0.51762 (14)	0.8202 (5)	0.6423 (2)	0.0495 (6)
C2	0.59839 (13)	0.7416 (5)	0.71598 (18)	0.0470 (6)
H2	0.6115	0.5906	0.7132	0.056*
C3	0.65267 (13)	0.8809 (4)	0.78604 (17)	0.0429 (5)
H3	0.6374	1.0308	0.7861	0.051*
C4	0.73402 (12)	0.8232 (4)	0.86323 (17)	0.0383 (5)
C5	0.77901 (14)	0.9756 (4)	0.94391 (19)	0.0469 (5)
H5	0.7576	1.1150	0.9460	0.056*
C6	0.85484 (15)	0.9234 (5)	1.0209 (2)	0.0520 (6)
H6	0.8835	1.0278	1.0741	0.062*
C7	0.88884 (13)	0.7179 (5)	1.02006 (18)	0.0482 (6)
C8	0.84507 (14)	0.5688 (5)	0.9386 (2)	0.0523 (6)
H8	0.8672	0.4316	0.9355	0.063*
C9	0.76890 (13)	0.6194 (4)	0.86135 (18)	0.0459 (6)
H9	0.7407	0.5157	0.8076	0.055*
C10	0.97104 (15)	0.6567 (8)	1.1064 (2)	0.0751 (10)
H10A	0.9802	0.7163	1.1717	0.113*
H10B	1.0082	0.7211	1.0910	0.113*
H10C	0.9767	0.4938	1.1112	0.113*
C11	0.46029 (14)	0.6396 (4)	0.57787 (19)	0.0474 (6)
H11	0.4775	0.4907	0.5810	0.057*
C12	0.38539 (13)	0.6886 (5)	0.51634 (17)	0.0439 (5)
H12	0.3713	0.8398	0.5164	0.053*
C13	0.32183 (13)	0.5337 (4)	0.44805 (17)	0.0405 (5)
C14	0.33464 (13)	0.3184 (4)	0.41838 (19)	0.0447 (5)
H14	0.3856	0.2673	0.4444	0.054*
C15	0.27265 (14)	0.1824 (4)	0.35119 (18)	0.0444 (5)
H15	0.2822	0.0410	0.3318	0.053*
C16	0.19537 (14)	0.2537 (4)	0.31160 (18)	0.0432 (5)
C17	0.18269 (14)	0.4658 (4)	0.34177 (19)	0.0455 (5)
H17	0.1318	0.5159	0.3167	0.055*
C18	0.24460 (13)	0.6022 (4)	0.40822 (18)	0.0438 (5)
H18	0.2348	0.7438	0.4271	0.053*
C19	0.12788 (15)	0.1027 (5)	0.2395 (2)	0.0596 (7)
H19A	0.1447	−0.0047	0.2065	0.089*
H19B	0.0862	0.1944	0.1871	0.089*
H19C	0.1097	0.0220	0.2790	0.089*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0515 (11)	0.0599 (12)	0.0763 (14)	0.0052 (10)	0.0073 (10)	−0.0046 (11)
C1	0.0385 (12)	0.0582 (15)	0.0410 (13)	0.0011 (11)	0.0128 (10)	−0.0008 (12)
C2	0.0365 (11)	0.0545 (14)	0.0420 (12)	0.0027 (11)	0.0146 (10)	0.0004 (11)
C3	0.0392 (11)	0.0471 (12)	0.0406 (12)	0.0013 (11)	0.0194 (10)	0.0008 (10)
C4	0.0339 (10)	0.0444 (11)	0.0356 (11)	−0.0026 (9)	0.0171 (9)	0.0000 (10)
C5	0.0474 (13)	0.0427 (11)	0.0500 (13)	−0.0041 (10)	0.0247 (11)	−0.0086 (11)
C6	0.0436 (13)	0.0587 (15)	0.0446 (13)	−0.0127 (12)	0.0162 (11)	−0.0164 (12)
C7	0.0342 (11)	0.0621 (15)	0.0434 (13)	−0.0031 (11)	0.0164 (10)	0.0021 (13)
C8	0.0422 (12)	0.0522 (14)	0.0591 (15)	0.0055 (11)	0.0236 (11)	−0.0037 (13)
C9	0.0398 (12)	0.0466 (12)	0.0456 (13)	−0.0060 (10)	0.0179 (10)	−0.0144 (11)
C10	0.0380 (13)	0.098 (3)	0.0664 (18)	0.0033 (17)	0.0103 (13)	0.0052 (19)
C11	0.0432 (12)	0.0502 (13)	0.0443 (13)	0.0016 (11)	0.0193 (10)	0.0002 (11)
C12	0.0431 (12)	0.0469 (11)	0.0406 (12)	0.0004 (11)	0.0208 (10)	0.0016 (10)
C13	0.0415 (11)	0.0430 (11)	0.0341 (11)	−0.0038 (10)	0.0173 (9)	0.0034 (10)
C14	0.0403 (11)	0.0485 (12)	0.0451 (12)	0.0046 (10)	0.0219 (10)	0.0066 (11)
C15	0.0518 (13)	0.0388 (10)	0.0449 (12)	−0.0001 (10)	0.0265 (11)	0.0004 (10)
C16	0.0461 (12)	0.0426 (11)	0.0384 (11)	−0.0039 (10)	0.0201 (10)	0.0035 (9)
C17	0.0368 (11)	0.0469 (12)	0.0483 (13)	0.0041 (10)	0.0187 (10)	0.0076 (11)
C18	0.0445 (12)	0.0418 (11)	0.0459 (13)	0.0042 (10)	0.0238 (10)	0.0041 (10)
C19	0.0507 (14)	0.0595 (16)	0.0560 (15)	−0.0103 (13)	0.0185 (12)	−0.0065 (14)

Geometric parameters (Å, º) top

O1—C1	1.211 (4)	C10—H10C	0.9600
C1—C2	1.480 (3)	C11—C12	1.320 (3)
C1—C11	1.490 (4)	C11—H11	0.9300
C2—C3	1.329 (3)	C12—C13	1.463 (3)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.465 (3)	C13—C18	1.394 (3)
C3—H3	0.9300	C13—C14	1.404 (3)
C4—C9	1.390 (3)	C14—C15	1.375 (3)
C4—C5	1.393 (3)	C14—H14	0.9300
C5—C6	1.382 (4)	C15—C16	1.400 (3)
C5—H5	0.9300	C15—H15	0.9300
C6—C7	1.386 (4)	C16—C17	1.390 (3)
C6—H6	0.9300	C16—C19	1.503 (3)
C7—C8	1.383 (4)	C17—C18	1.373 (3)
C7—C10	1.516 (3)	C17—H17	0.9300
C8—C9	1.385 (3)	C18—H18	0.9300
C8—H8	0.9300	C19—H19A	0.9600
C9—H9	0.9300	C19—H19B	0.9600
C10—H10A	0.9600	C19—H19C	0.9600
C10—H10B	0.9600

O1—C1—C2	121.5 (3)	H10B—C10—H10C	109.5
O1—C1—C11	122.5 (2)	C12—C11—C1	120.7 (2)
C2—C1—C11	116.0 (2)	C12—C11—H11	119.6
C3—C2—C1	121.8 (2)	C1—C11—H11	119.6
C3—C2—H2	119.1	C11—C12—C13	127.8 (2)
C1—C2—H2	119.1	C11—C12—H12	116.1
C2—C3—C4	126.8 (2)	C13—C12—H12	116.1
C2—C3—H3	116.6	C18—C13—C14	117.7 (2)
C4—C3—H3	116.6	C18—C13—C12	119.2 (2)
C9—C4—C5	117.6 (2)	C14—C13—C12	123.0 (2)
C9—C4—C3	123.1 (2)	C15—C14—C13	120.7 (2)
C5—C4—C3	119.4 (2)	C15—C14—H14	119.7
C6—C5—C4	121.2 (2)	C13—C14—H14	119.7
C6—C5—H5	119.4	C14—C15—C16	121.0 (2)
C4—C5—H5	119.4	C14—C15—H15	119.5
C5—C6—C7	121.1 (2)	C16—C15—H15	119.5
C5—C6—H6	119.5	C17—C16—C15	118.3 (2)
C7—C6—H6	119.5	C17—C16—C19	120.9 (2)
C8—C7—C6	117.9 (2)	C15—C16—C19	120.7 (2)
C8—C7—C10	120.9 (3)	C18—C17—C16	120.6 (2)
C6—C7—C10	121.2 (3)	C18—C17—H17	119.7
C7—C8—C9	121.4 (3)	C16—C17—H17	119.7
C7—C8—H8	119.3	C17—C18—C13	121.7 (2)
C9—C8—H8	119.3	C17—C18—H18	119.2
C8—C9—C4	120.9 (2)	C13—C18—H18	119.2
C8—C9—H9	119.6	C16—C19—H19A	109.5
C4—C9—H9	119.6	C16—C19—H19B	109.5
C7—C10—H10A	109.5	H19A—C19—H19B	109.5
C7—C10—H10B	109.5	C16—C19—H19C	109.5
H10A—C10—H10B	109.5	H19A—C19—H19C	109.5
C7—C10—H10C	109.5	H19B—C19—H19C	109.5
H10A—C10—H10C	109.5

O1—C1—C2—C3	6.0 (4)	O1—C1—C11—C12	−4.0 (4)
C11—C1—C2—C3	−172.2 (2)	C2—C1—C11—C12	174.1 (2)
C1—C2—C3—C4	179.6 (2)	C1—C11—C12—C13	179.6 (2)
C2—C3—C4—C9	11.2 (4)	C11—C12—C13—C18	164.8 (2)
C2—C3—C4—C5	−167.6 (2)	C11—C12—C13—C14	−16.6 (4)
C9—C4—C5—C6	−1.7 (4)	C18—C13—C14—C15	0.8 (3)
C3—C4—C5—C6	177.1 (2)	C12—C13—C14—C15	−177.9 (2)
C4—C5—C6—C7	0.4 (4)	C13—C14—C15—C16	−0.7 (3)
C5—C6—C7—C8	1.3 (4)	C14—C15—C16—C17	0.1 (3)
C5—C6—C7—C10	−177.9 (3)	C14—C15—C16—C19	−179.0 (2)
C6—C7—C8—C9	−1.6 (4)	C15—C16—C17—C18	0.4 (3)
C10—C7—C8—C9	177.6 (3)	C19—C16—C17—C18	179.5 (2)
C7—C8—C9—C4	0.2 (4)	C16—C17—C18—C13	−0.3 (3)
C5—C4—C9—C8	1.5 (4)	C14—C13—C18—C17	−0.3 (3)
C3—C4—C9—C8	−177.4 (2)	C12—C13—C18—C17	178.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1	0.93	2.49	2.817 (4)	101
C12—H12···O1	0.93	2.48	2.819 (3)	102
C5—H5···CgAⁱ	0.93	2.82	3.523 (3)	133
C9—H9···CgBⁱⁱ	0.93	2.89	3.604 (3)	134
C18—H18···CgBⁱⁱⁱ	0.93	2.95	3.621 (3)	131

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₈O
M_r	262.33
Crystal system, space group	Monoclinic, C2
Temperature (K)	296
a, b, c (Å)	19.937 (2), 5.8637 (5), 14.9207 (14)
β (°)	121.001 (3)
V (Å³)	1495.1 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.25 × 0.20 × 0.15

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.980, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	9611, 2288, 1800
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.695

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.137, 1.04
No. of reflections	2288
No. of parameters	183
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.21
Absolute structure	Flack (1983), 726 Friedel pairs

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2003), WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1	0.93	2.49	2.817 (4)	101
C12—H12···O1	0.93	2.48	2.819 (3)	102
C5—H5···CgAⁱ	0.93	2.82	3.523 (3)	133
C9—H9···CgBⁱⁱ	0.93	2.89	3.604 (3)	134
C18—H18···CgBⁱⁱⁱ	0.93	2.95	3.621 (3)	131

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

Acknowledgements

MNA gratefully acknowledges the Higher Education Commision, Islamabad, Pakistan, for providing a scholarship under the Indigenous PhD Programme (PIN 042-120607-PS2-183).

References

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