2-(4-Bromo­phen­yl)-2-oxoethyl naphthalene-1-carboxyl­ate

Garudachari, B.; Isloor, A.M.; Gerber, T.; Hosten, E.; Betz, R.

doi:10.1107/S160053681300843X

organic compounds

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ISSN: 2056-9890

Volume 69| Part 5| May 2013| Page o649

https://doi.org/10.1107/S160053681300843X

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2-(4-Bromophenyl)-2-oxoethyl naphthalene-1-carboxylate

Bhadrachari Garudachari,^a Arun M. Isloor,^a Thomas Gerber,^b Eric Hosten ^b and Richard Betz ^b ^*

^aNational Institute of Technology-Karnataka, Department of Chemistry, Surathkal, Mangalore 575 025, India, and ^bNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa
^*Correspondence e-mail: richard.betz@webmail.co.za

(Received 26 February 2013; accepted 27 March 2013; online 5 April 2013)

In the title compound, C₁₉H₁₃BrO₃, an ester of 1-naphthoic acid with an aromatic alcohol, the least-squares planes defined by the C atoms of the respective aromatic systems enclose an angle of 77.20 (5)°. In the crystal, C—H⋯O contacts connect the molecules into undulating sheets parallel (100).

Related literature

For general information about phenacyl bromide derivatives, see: Rather & Reid (1919 ). For the photolytic properties of phenyl benzoates, see: Sheehan & Umezaw (1973 ); Ruzicka et al. (2002 ); Litera et al. (2006 ). For synthetic applications of phenyl benzoates, see: Huang et al. (1996 ); Gandhi et al. (1995 ). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ); Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₉H₁₃BrO₃
M_r = 369.20
Monoclinic, P 2₁ /c
a = 5.2888 (2) Å
b = 14.9139 (6) Å
c = 20.0275 (8) Å
β = 100.867 (2)°
V = 1551.37 (11) Å³
Z = 4
Mo Kα radiation
μ = 2.66 mm⁻¹
T = 200 K
0.35 × 0.16 × 0.07 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2010 ) T_min = 0.656, T_max = 0.746
14937 measured reflections
3848 independent reflections
2712 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.080
S = 1.02
3848 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.56 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O1ⁱ	0.95	2.41	3.240 (3)	146
C23—H23⋯O3ⁱⁱ	0.95	2.51	3.292 (3)	140
Symmetry codes: (i) -x+1, -y, -z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; 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, 2012 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681300843X/qk2054sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681300843X/qk2054Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S160053681300843X/qk2054Isup3.cdx

Supporting information file. DOI: https://doi.org/10.1107/S160053681300843X/qk2054Isup4.cml

checkCIF report

Comment top

For decades, phenacyl bromide derivatives have found ample application in the identification of organic acids (Rather & Reid, 1919). These compounds can be photolysed under neutral and mild conditions (Sheehan & Umezaw, 1973; Ruzicka et al., 2002; Litera et al., 2006). They also find application in the field of synthetic chemistry such as in the synthesis of oxazoles and imidazoles (Huang et al., 1996) as well as benzoxazepine (Gandhi et al., 1995). In continuation of our research focused on the crystal structures of medical compounds, the title compound was synthesized.

The planes defined by the atoms of the carboxy group on the one hand and the non-hydrogen atoms of the CH₂–C═O moiety intersect at an angle of 78.8 (3) °. The least-squares planes defined by the carbon atoms of the respective aromatic systems enclose an angle of 77.20 (5) ° (Fig. 1).

In the crystal, intermolecular C–H···O contacts are observed whose range falls by more than 0.2 Å below the sum of van-der-Waals radii of the atoms participating. One of the hydrogen atoms of the brominated phenyl moiety and the oxygen atom of the keto group give rise to centrosymmetric dimers. Additionally, the hydrogen atom in para position to the carboxy moiety forms a C–H···O contact to the double bonded oxygen atom of exactly this group in a neighbouring molecule. In total, the molecules are connected to undulated sheets parallel (100). In terms of graph-set analysis (Etter et al., 1990; Bernstein et al., 1995), the descriptor for these contacts is C¹₁(7)R²₂(10) on the unary level. Information about metrical parameters as well as the symmetry of those contacts has been summarized in Table 1. The shortest intercentroid distance between two aromatic systems was measured at 4.7943 (14) Å and is apparent between the two different rings in the naphthoic acid moiety and its symmetry-generated equivalents (Fig. 2).

Related literature top

For general information about phenacyl bromide derivatives, see: Rather & Reid (1919). For the photolytic properties of phenyl benzoates, see: Sheehan & Umezaw (1973); Ruzicka et al. (2002); Litera et al. (2006). For synthetic applications of phenyl benzoates, see: Huang et al. (1996); Gandhi et al. (1995). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995).

Experimental top

A mixture of naphthalene-1-carboxylic acid (0.1 g, 0.5 mmol), potassium carbonate (0.087 g, 0.63 mmol) and 2-bromo-1-(4-bromophenyl)ethanone (0.174 g, 0.63 mmol) in dimethylformamide (5 ml) was stirred at room temperature for 2 h. After completion of the reaction, the reaction mixture was poured into ice-cold water. The solid product obtained was filtered, washed with water and recrystallized from ethanol (yield: 0.19 g, 90.4%).

Structure description top

For general information about phenacyl bromide derivatives, see: Rather & Reid (1919). For the photolytic properties of phenyl benzoates, see: Sheehan & Umezaw (1973); Ruzicka et al. (2002); Litera et al. (2006). For synthetic applications of phenyl benzoates, see: Huang et al. (1996); Gandhi et al. (1995). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995).

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); 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, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and anisotropic displacement ellipsoids (drawn at 50% probability level).
	Fig. 2. Intermolecular contacts, viewed along [-1 0 0]. Symmetry operators: ⁱ -x + 1, y - 1/2, -z + 1/2; ⁱⁱ -x + 1, y + 1/2, -z + 1/2; ⁱⁱⁱ -x + 1, -y, -z.

2-(4-Bromophenyl)-2-oxoethyl naphthalene-1-carboxylate top

Crystal data top

C₁₉H₁₃BrO₃	F(000) = 744
M_r = 369.20	D_x = 1.581 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 406–404 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 5.2888 (2) Å	Cell parameters from 4237 reflections
b = 14.9139 (6) Å	θ = 2.5–24.2°
c = 20.0275 (8) Å	µ = 2.66 mm⁻¹
β = 100.867 (2)°	T = 200 K
V = 1551.37 (11) Å³	Platelet, colourless
Z = 4	0.35 × 0.16 × 0.07 mm

Data collection top

Bruker APEXII CCD diffractometer	3848 independent reflections
Radiation source: fine-focus sealed tube	2712 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
φ and ω scans	θ_max = 28.4°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2010)	h = −6→7
T_min = 0.656, T_max = 0.746	k = −19→19
14937 measured reflections	l = −26→26

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.080	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0326P)² + 0.6176P] where P = (F_o² + 2F_c²)/3
3848 reflections	(Δ/σ)_max = 0.001
208 parameters	Δρ_max = 0.55 e Å⁻³
0 restraints	Δρ_min = −0.56 e Å⁻³

Crystal data top

C₁₉H₁₃BrO₃	V = 1551.37 (11) Å³
M_r = 369.20	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.2888 (2) Å	µ = 2.66 mm⁻¹
b = 14.9139 (6) Å	T = 200 K
c = 20.0275 (8) Å	0.35 × 0.16 × 0.07 mm
β = 100.867 (2)°

Data collection top

Bruker APEXII CCD diffractometer	3848 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2010)	2712 reflections with I > 2σ(I)
T_min = 0.656, T_max = 0.746	R_int = 0.026
14937 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.080	H-atom parameters constrained
S = 1.02	Δρ_max = 0.55 e Å⁻³
3848 reflections	Δρ_min = −0.56 e Å⁻³
208 parameters

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

	x	y	z	U_iso*/U_eq
Br1	1.05155 (5)	−0.337459 (17)	−0.082915 (14)	0.05483 (11)
O1	0.7161 (3)	0.01926 (12)	0.09358 (8)	0.0504 (4)
O2	1.0379 (3)	0.07451 (10)	0.20022 (7)	0.0383 (3)
O3	0.8211 (3)	−0.03018 (11)	0.24600 (9)	0.0561 (5)
C1	0.9200 (4)	−0.02042 (15)	0.10258 (10)	0.0324 (5)
C2	1.1300 (4)	0.00494 (16)	0.16236 (11)	0.0392 (5)
H2A	1.1784	−0.0480	0.1918	0.047*
H2B	1.2847	0.0257	0.1457	0.047*
C3	0.8587 (4)	0.04763 (15)	0.23606 (11)	0.0356 (5)
C11	0.9659 (4)	−0.09457 (14)	0.05693 (10)	0.0301 (4)
C12	0.7748 (4)	−0.11433 (15)	0.00128 (11)	0.0364 (5)
H12	0.6242	−0.0782	−0.0078	0.044*
C13	0.7996 (4)	−0.18520 (15)	−0.04088 (12)	0.0396 (5)
H13	0.6679	−0.1981	−0.0789	0.047*
C14	1.0190 (4)	−0.23729 (14)	−0.02702 (11)	0.0359 (5)
C15	1.2131 (4)	−0.21891 (16)	0.02701 (12)	0.0411 (5)
H15	1.3637	−0.2550	0.0356	0.049*
C16	1.1865 (4)	−0.14699 (15)	0.06894 (11)	0.0376 (5)
H16	1.3206	−0.1335	0.1063	0.045*
C20	0.7119 (4)	0.12388 (14)	0.25724 (10)	0.0317 (4)
C21	0.6958 (4)	0.20194 (15)	0.22036 (11)	0.0401 (5)
H21	0.7954	0.2086	0.1858	0.048*
C22	0.5341 (5)	0.27215 (16)	0.23293 (13)	0.0505 (6)
H22	0.5277	0.3263	0.2077	0.061*
C23	0.3868 (5)	0.26250 (17)	0.28116 (13)	0.0486 (6)
H23	0.2727	0.3093	0.2880	0.058*
C24	0.3998 (4)	0.18466 (16)	0.32119 (12)	0.0397 (5)
C25	0.2488 (4)	0.17481 (19)	0.37226 (14)	0.0517 (7)
H25	0.1312	0.2208	0.3785	0.062*
C26	0.2694 (5)	0.1008 (2)	0.41240 (14)	0.0572 (7)
H26	0.1656	0.0950	0.4460	0.069*
C27	0.4432 (5)	0.03358 (19)	0.40408 (13)	0.0525 (7)
H27	0.4620	−0.0169	0.4335	0.063*
C28	0.5868 (4)	0.03887 (16)	0.35440 (11)	0.0406 (5)
H28	0.7011	−0.0086	0.3491	0.049*
C29	0.5685 (4)	0.11383 (14)	0.31069 (10)	0.0316 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0741 (2)	0.04066 (15)	0.05347 (17)	0.00681 (13)	0.02159 (13)	−0.00796 (12)
O1	0.0365 (9)	0.0641 (12)	0.0454 (10)	0.0178 (8)	−0.0056 (7)	−0.0172 (8)
O2	0.0327 (8)	0.0439 (9)	0.0381 (8)	−0.0067 (7)	0.0063 (6)	−0.0090 (7)
O3	0.0770 (12)	0.0334 (10)	0.0665 (12)	0.0033 (9)	0.0357 (10)	−0.0005 (8)
C1	0.0258 (10)	0.0375 (12)	0.0325 (11)	0.0027 (9)	0.0020 (8)	−0.0001 (9)
C2	0.0280 (11)	0.0523 (14)	0.0365 (12)	0.0004 (10)	0.0040 (9)	−0.0084 (10)
C3	0.0354 (11)	0.0387 (13)	0.0314 (11)	−0.0017 (9)	0.0029 (9)	−0.0038 (9)
C11	0.0241 (10)	0.0378 (12)	0.0280 (10)	0.0017 (8)	0.0045 (8)	0.0034 (9)
C12	0.0293 (11)	0.0410 (13)	0.0367 (12)	0.0059 (9)	0.0007 (9)	−0.0017 (9)
C13	0.0378 (12)	0.0413 (13)	0.0365 (12)	0.0011 (10)	−0.0009 (9)	−0.0036 (10)
C14	0.0439 (12)	0.0322 (12)	0.0349 (12)	0.0037 (10)	0.0156 (10)	0.0017 (9)
C15	0.0343 (11)	0.0449 (14)	0.0443 (13)	0.0134 (10)	0.0083 (10)	0.0025 (10)
C16	0.0258 (10)	0.0519 (15)	0.0333 (11)	0.0064 (9)	0.0009 (9)	0.0000 (10)
C20	0.0306 (10)	0.0303 (11)	0.0311 (11)	−0.0012 (9)	−0.0020 (8)	−0.0042 (9)
C21	0.0464 (13)	0.0365 (12)	0.0344 (12)	−0.0041 (10)	0.0002 (10)	0.0003 (10)
C22	0.0635 (16)	0.0312 (13)	0.0491 (15)	0.0058 (12)	−0.0093 (13)	0.0008 (11)
C23	0.0470 (14)	0.0399 (14)	0.0519 (15)	0.0100 (11)	−0.0082 (12)	−0.0152 (11)
C24	0.0323 (11)	0.0432 (13)	0.0390 (12)	−0.0018 (10)	−0.0046 (9)	−0.0175 (10)
C25	0.0337 (12)	0.0657 (19)	0.0556 (16)	−0.0054 (12)	0.0080 (11)	−0.0334 (14)
C26	0.0491 (15)	0.076 (2)	0.0510 (16)	−0.0235 (14)	0.0201 (12)	−0.0227 (14)
C27	0.0607 (16)	0.0560 (17)	0.0428 (14)	−0.0237 (13)	0.0147 (12)	−0.0050 (12)
C28	0.0440 (12)	0.0374 (13)	0.0404 (13)	−0.0073 (10)	0.0078 (10)	−0.0025 (10)
C29	0.0279 (10)	0.0334 (12)	0.0302 (11)	−0.0044 (9)	−0.0025 (8)	−0.0079 (8)

Geometric parameters (Å, º) top

Br1—C14	1.894 (2)	C16—H16	0.9500
O1—C1	1.213 (2)	C20—C21	1.373 (3)
O2—C3	1.353 (3)	C20—C29	1.432 (3)
O2—C2	1.424 (2)	C21—C22	1.404 (3)
O3—C3	1.200 (3)	C21—H21	0.9500
C1—C11	1.484 (3)	C22—C23	1.358 (4)
C1—C2	1.520 (3)	C22—H22	0.9500
C2—H2A	0.9900	C23—C24	1.405 (3)
C2—H2B	0.9900	C23—H23	0.9500
C3—C20	1.483 (3)	C24—C25	1.419 (3)
C11—C16	1.387 (3)	C24—C29	1.424 (3)
C11—C12	1.388 (3)	C25—C26	1.357 (4)
C12—C13	1.374 (3)	C25—H25	0.9500
C12—H12	0.9500	C26—C27	1.392 (4)
C13—C14	1.380 (3)	C26—H26	0.9500
C13—H13	0.9500	C27—C28	1.363 (3)
C14—C15	1.371 (3)	C27—H27	0.9500
C15—C16	1.386 (3)	C28—C29	1.412 (3)
C15—H15	0.9500	C28—H28	0.9500

C3—O2—C2	114.25 (17)	C21—C20—C29	120.2 (2)
O1—C1—C11	121.08 (18)	C21—C20—C3	118.6 (2)
O1—C1—C2	119.53 (19)	C29—C20—C3	120.87 (19)
C11—C1—C2	119.38 (17)	C20—C21—C22	120.9 (2)
O2—C2—C1	109.17 (16)	C20—C21—H21	119.5
O2—C2—H2A	109.8	C22—C21—H21	119.5
C1—C2—H2A	109.8	C23—C22—C21	119.9 (2)
O2—C2—H2B	109.8	C23—C22—H22	120.0
C1—C2—H2B	109.8	C21—C22—H22	120.0
H2A—C2—H2B	108.3	C22—C23—C24	121.4 (2)
O3—C3—O2	121.9 (2)	C22—C23—H23	119.3
O3—C3—C20	125.6 (2)	C24—C23—H23	119.3
O2—C3—C20	112.42 (19)	C23—C24—C25	121.6 (2)
C16—C11—C12	118.8 (2)	C23—C24—C29	119.6 (2)
C16—C11—C1	122.91 (18)	C25—C24—C29	118.9 (2)
C12—C11—C1	118.29 (17)	C26—C25—C24	121.2 (2)
C13—C12—C11	121.14 (19)	C26—C25—H25	119.4
C13—C12—H12	119.4	C24—C25—H25	119.4
C11—C12—H12	119.4	C25—C26—C27	119.7 (2)
C12—C13—C14	118.9 (2)	C25—C26—H26	120.1
C12—C13—H13	120.6	C27—C26—H26	120.1
C14—C13—H13	120.6	C28—C27—C26	121.1 (3)
C15—C14—C13	121.5 (2)	C28—C27—H27	119.4
C15—C14—Br1	119.07 (16)	C26—C27—H27	119.4
C13—C14—Br1	119.46 (17)	C27—C28—C29	121.0 (2)
C14—C15—C16	119.11 (19)	C27—C28—H28	119.5
C14—C15—H15	120.4	C29—C28—H28	119.5
C16—C15—H15	120.4	C28—C29—C24	117.9 (2)
C15—C16—C11	120.6 (2)	C28—C29—C20	124.22 (19)
C15—C16—H16	119.7	C24—C29—C20	117.9 (2)
C11—C16—H16	119.7

C3—O2—C2—C1	71.6 (2)	O2—C3—C20—C29	−162.04 (17)
O1—C1—C2—O2	1.4 (3)	C29—C20—C21—C22	−1.7 (3)
C11—C1—C2—O2	−177.41 (18)	C3—C20—C21—C22	172.2 (2)
C2—O2—C3—O3	14.5 (3)	C20—C21—C22—C23	−1.4 (3)
C2—O2—C3—C20	−162.58 (16)	C21—C22—C23—C24	2.6 (4)
O1—C1—C11—C16	−173.9 (2)	C22—C23—C24—C25	179.1 (2)
C2—C1—C11—C16	4.9 (3)	C22—C23—C24—C29	−0.7 (3)
O1—C1—C11—C12	3.5 (3)	C23—C24—C25—C26	−177.5 (2)
C2—C1—C11—C12	−177.7 (2)	C29—C24—C25—C26	2.3 (3)
C16—C11—C12—C13	1.0 (3)	C24—C25—C26—C27	0.7 (4)
C1—C11—C12—C13	−176.5 (2)	C25—C26—C27—C28	−2.6 (4)
C11—C12—C13—C14	0.2 (3)	C26—C27—C28—C29	1.5 (4)
C12—C13—C14—C15	−1.1 (3)	C27—C28—C29—C24	1.5 (3)
C12—C13—C14—Br1	178.04 (17)	C27—C28—C29—C20	−179.7 (2)
C13—C14—C15—C16	0.7 (3)	C23—C24—C29—C28	176.54 (19)
Br1—C14—C15—C16	−178.38 (17)	C25—C24—C29—C28	−3.3 (3)
C14—C15—C16—C11	0.5 (3)	C23—C24—C29—C20	−2.4 (3)
C12—C11—C16—C15	−1.4 (3)	C25—C24—C29—C20	177.78 (19)
C1—C11—C16—C15	176.0 (2)	C21—C20—C29—C28	−175.28 (19)
O3—C3—C20—C21	−152.8 (2)	C3—C20—C29—C28	11.0 (3)
O2—C3—C20—C21	24.1 (3)	C21—C20—C29—C24	3.6 (3)
O3—C3—C20—C29	21.0 (3)	C3—C20—C29—C24	−170.16 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1ⁱ	0.95	2.41	3.240 (3)	146
C23—H23···O3ⁱⁱ	0.95	2.51	3.292 (3)	140

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₃BrO₃
M_r	369.20
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	200
a, b, c (Å)	5.2888 (2), 14.9139 (6), 20.0275 (8)
β (°)	100.867 (2)
V (Å³)	1551.37 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.66
Crystal size (mm)	0.35 × 0.16 × 0.07

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2010)
T_min, T_max	0.656, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	14937, 3848, 2712
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.670

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.080, 1.02
No. of reflections	3848
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.56

Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1ⁱ	0.95	2.41	3.240 (3)	146.2
C23—H23···O3ⁱⁱ	0.95	2.51	3.292 (3)	139.5

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

Acknowledgements

AMI thanks Professor Swapan Bhattacharya, Director of the National Institute of Technology Karnataka, Surathkal, India, for his encouragement and providing the research facilities. AMI also thanks the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India for the 'Young Scientist' award.

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