[3-Benzoyl-2,4-bis­(3-nitro­phen­yl)cyclo­but­yl](phen­yl)methanone

Nayak, P.S.; Narayana, B.; Yathirajan, H.S.; Gerber, T.; Hosten, E.; Betz, R.

doi:10.1107/S1600536812044650

organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Pages o3272-o3273

doi:10.1107/S1600536812044650

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[3-Benzoyl-2,4-bis(3-nitrophenyl)cyclobutyl](phenyl)methanone

Prakash S. Nayak,^a Badiadka Narayana,^a Hemmige S. Yathirajan,^b Thomas Gerber,^c Eric Hosten ^c and Richard Betz ^c ^*

^aMangalore University, Department of Studies in Chemistry, Mangalagangotri 574 199, India, ^bUniversity of Mysore, Department of Studies in Chemistry, Manasagangotri, Mysore 570 006, India, and ^cNelson 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 15 October 2012; accepted 29 October 2012; online 3 November 2012)

The asymmetric unit of the title compound, C₃₀H₂₂N₂O₆, comprises a half-molecule of the cyclobutane derivative. The least-squares planes defined by the respective C atoms of the aromatic substituents intersect at angles of 76.81 (7) and 89.22 (8)° with the least-squares plane defined by the C atoms of the cyclobutane ring. In the crystal, C—H⋯O contacts connect the molecules into a three-dimensional network. The shortest centroid–centroid distance between the two different aromatic rings is 3.9601 (8) Å.

Related literature

For the biological activity of chalcones and cyclobutane-derived compounds, see: Dimmock et al. (1999 ); Marais et al. (2005 ); Katerere et al. (2004 ); Seidel et al. (2000 ). For the crystal structures of similar compounds, see: Zheng et al. (2001 ); Zhuang & Zheng (2002 ). For general information about the dimerization of chalcones, see: Stobbe & Bremer (1929 ); Mustafa (1952 ). For puckering analysis of cyclic motifs, see: Cremer & Pople (1975 ). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990 ); Bernstein et al. (1995 ).

Experimental

Crystal data

C₃₀H₂₂N₂O₆
M_r = 506.50
Monoclinic, P 2₁ /c
a = 5.7850 (1) Å
b = 14.7824 (3) Å
c = 14.3589 (3) Å
β = 104.858 (1)°
V = 1186.86 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 200 K
0.33 × 0.14 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.968, T_max = 0.989
11005 measured reflections
2945 independent reflections
2387 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.111
S = 1.03
2945 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1ⁱ	1.00	2.56	3.3957 (15)	141
C14—H14⋯O2ⁱⁱ	0.95	2.56	3.3666 (19)	142
C2—H2⋯O3ⁱⁱⁱ	1.00	2.61	3.5009 (17)	148
Symmetry codes: (i) -x, -y, -z+1; (ii) x, y, z-1; (iii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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 (Farrugia, 2012 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812044650/fj2603sup1.cif

Supporting information file. DOI: 10.1107/S1600536812044650/fj2603Isup2.cdx

Structure factors: contains datablock I. DOI: 10.1107/S1600536812044650/fj2603Isup3.hkl

Supporting information file. DOI: 10.1107/S1600536812044650/fj2603Isup4.cml

checkCIF report

Comment top

Chalcones comprise one of the most commonly occurring classes of medicinally important natural compounds, since they show various biological activities (Dimmock et al., 1999; Marais et al.,. 2005). Cyclobutane-containing natural products have, e.g., been reported for Combretum albopunctatum (Katerere et al., 2004) and Goniothalamus thwaitesii (Seidel et al. 2000). Because of the various biological activities of these natural compounds, the synthesis of cyclobutane-derived compounds is one of the most intensively studied photochemical reactions of chalcone derivatives. These reactions can be carried out in solution, solid state and molten state by sunlight or UV-vis irradiation, with variable results in terms of yield and product composition (Stobbe & Bremer, 1929; Mustafa, 1952). The crystal structures of some dimerized chalcones such as r-1,c-2,t-3,t-4- 1,3-bis(4-methoxyphenyl)-2,4-bis(5-phenyl-1,3,4-oxadiazol-2-yl) cyclobutane 1,4-dioxane solvate (Zheng et al., 2001) and r-1,c-2,t- 3,t-4–1,2-bis(4-methoxyphenyl)-3,4-bis(5-phenyl-1,3,4-oxadiazol-2-yl) cyclobutane (Zhuang & Zheng, 2002) have been reported. In view of the pharmacological importance of chalcone derivatives, the synthesis of such a compound was attempted. Upon the determination of the reaction product's crystal structure, the unintentional formation of the corresponding dimer in the wake of the reaction sequence was revealed.

The title compound, [3-benzoyl-2,4-bis(3-nitrophenyl)cyclobutyl](phenyl)methanone, features a central cyclobutane moiety that bears one aromatic substituent on each carbon atom. Due to the centrosymmetry of the molecule, the relative orientation of these substituents corresponds to cis-trans-cis-trans. The small puckering amplitude precludes a puckering analysis of this ring (Cremer & Pople, 1975). The least-squares planes defined by the respective carbon atoms of the aromatic substituents intersect with the least-squares plane defined the carbon atoms of the cyclobutane ring at angles of 76.81 (7) ° and 89.22 (8) °. The aforementioned planes of the two different aromatic moieties in the asymmetric unit enclose an angle of 24.09 (6) ° (Fig. 1).

In the crystal, intermolecular C–H···O contacts whose range falls by more than 0.1 Å below the sum of van-der-Waals radii of the respective atoms can be observed. These are supported by the hydrogen atom in para position of the non-substituted phenyl group as well as all methine-type hydrogen atoms while the hydrogen atoms of the nitrophenyl moiety do not take part in such contacts. All oxygen atoms present in the molecule act as acceptors. Furthermore, one intramolecular C–H···O contact between a carbonyl group and a methine-type hydrogen atom is apparent. In total, the molecules are connected to a three-dimensional network. In terms of graph-set analysis (Etter et al., 1990; Bernstein et al., 1995), the descriptor for these contacts is S(5)C¹₁(8)C¹₁(13)R²₂(10) on the unary level. Metrical parameters as well as information about the symmetry of these contacts are summarized in Table 1. The shortest intercentroid distance between two aromatic systems was measured at 3.9601 (8) Å and is apparent between the two different aromatic substituents (Fig. 2).

The packing of the title compound in the crystal structure is shown in Figure 3.

Related literature top

For the biological activity of chalcones and cyclobutane-derived compounds, see: Dimmock et al. (1999); Marais et al. (2005); Katerere et al. (2004); Seidel et al. (2000). For the crystal structures of similar compounds, see: Zheng et al. (2001); Zhuang & Zheng (2002). For general information about the dimerization of chalcones, see: Stobbe & Bremer (1929); Mustafa (1952). For puckering analysis of cyclic motifs, see: Cremer & Pople (1975). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995).

Experimental top

To a mixture of 3-nitrobenzaldehyde (1.51 g, 0.01 mol) and acetophenone (1.16 ml, 0.01 mol) in ethanol (50 ml), a sodium hydroxide solution (10%, 10 ml) was added. The mixture was stirred at 278–283 K for 3 h. The precipitate formed was collected by filtration and purified by recrystallization from ethanol. Single crystals suitable for the X-ray diffraction study were grown from methanol by slow evaporation at room temperature. The synthesized chalcone was dimerized during crystallization.

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 (Farrugia, 2012) and Mercury (Macrae et al., 2008); 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). Symmetry operator: ⁱ -x + 1, -y, -z + 1.
	Fig. 2. Intermolecular contacts, viewed along [-1 0 0]. For clarity, only a selection of contacts is depicted. Symmetry operators: ⁱ x, y, z - 1; ⁱⁱ x, y, z + 1.
	Fig. 3. Molecular packing of the title compound, viewed along [-1 0 0] (anisotropic displacement ellipsoids drawn at 50% probability level).

[3-Benzoyl-2,4-bis(3-nitrophenyl)cyclobutyl](phenyl)methanone top

Crystal data top

C₃₀H₂₂N₂O₆	F(000) = 528
M_r = 506.50	D_x = 1.417 Mg m⁻³
Monoclinic, P2₁/c	Melting point > 523 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 5.7850 (1) Å	Cell parameters from 4849 reflections
b = 14.7824 (3) Å	θ = 2.8–28.3°
c = 14.3589 (3) Å	µ = 0.10 mm⁻¹
β = 104.858 (1)°	T = 200 K
V = 1186.86 (4) Å³	Block, colourless
Z = 2	0.33 × 0.14 × 0.11 mm

Data collection top

Bruker APEXII CCD diffractometer	2945 independent reflections
Radiation source: fine-focus sealed tube	2387 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ϕ and ω scans	θ_max = 28.5°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −7→7
T_min = 0.968, T_max = 0.989	k = −17→19
11005 measured reflections	l = −17→19

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.055P)² + 0.3935P] where P = (F_o² + 2F_c²)/3
2945 reflections	(Δ/σ)_max < 0.001
172 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₃₀H₂₂N₂O₆	V = 1186.86 (4) Å³
M_r = 506.50	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.7850 (1) Å	µ = 0.10 mm⁻¹
b = 14.7824 (3) Å	T = 200 K
c = 14.3589 (3) Å	0.33 × 0.14 × 0.11 mm
β = 104.858 (1)°

Data collection top

Bruker APEXII CCD diffractometer	2945 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2387 reflections with I > 2σ(I)
T_min = 0.968, T_max = 0.989	R_int = 0.020
11005 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.111	H-atom parameters constrained
S = 1.03	Δρ_max = 0.32 e Å⁻³
2945 reflections	Δρ_min = −0.22 e Å⁻³
172 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.02716 (16)	0.08341 (7)	0.41101 (7)	0.0343 (2)
O2	0.4112 (3)	0.11125 (12)	0.89447 (9)	0.0693 (4)
O3	0.6594 (3)	0.21980 (8)	0.94461 (8)	0.0584 (4)
N1	0.5674 (2)	0.16321 (9)	0.88471 (8)	0.0386 (3)
C1	0.2098 (2)	0.07918 (8)	0.38436 (8)	0.0223 (2)
C2	0.4494 (2)	0.05901 (8)	0.45303 (8)	0.0206 (2)
H2	0.5684	0.1074	0.4506	0.025*
C3	0.44539 (19)	0.03813 (8)	0.55776 (8)	0.0203 (2)
H3	0.2767	0.0331	0.5629	0.024*
C11	0.2032 (2)	0.09061 (8)	0.28021 (8)	0.0224 (2)
C12	0.3971 (2)	0.12395 (9)	0.24994 (9)	0.0266 (3)
H12	0.5414	0.1391	0.2960	0.032*
C13	0.3792 (2)	0.13495 (10)	0.15237 (9)	0.0333 (3)
H13	0.5096	0.1596	0.1318	0.040*
C14	0.1718 (3)	0.11009 (11)	0.08487 (10)	0.0371 (3)
H14	0.1607	0.1173	0.0181	0.045*
C15	−0.0192 (2)	0.07487 (10)	0.11440 (9)	0.0358 (3)
H15	−0.1599	0.0565	0.0680	0.043*
C16	−0.0049 (2)	0.06645 (9)	0.21178 (9)	0.0287 (3)
H16	−0.1381	0.0440	0.2320	0.034*
C21	0.5883 (2)	0.09762 (8)	0.63665 (8)	0.0209 (2)
C22	0.5151 (2)	0.10549 (8)	0.72138 (8)	0.0245 (2)
H22	0.3736	0.0762	0.7275	0.029*
C23	0.6502 (2)	0.15632 (8)	0.79654 (9)	0.0276 (3)
C24	0.8559 (2)	0.20118 (9)	0.79156 (9)	0.0319 (3)
H24	0.9447	0.2362	0.8441	0.038*
C25	0.9279 (2)	0.19330 (9)	0.70728 (10)	0.0307 (3)
H25	1.0684	0.2235	0.7015	0.037*
C26	0.7973 (2)	0.14165 (8)	0.63095 (9)	0.0254 (2)
H26	0.8512	0.1363	0.5740	0.030*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0268 (4)	0.0478 (6)	0.0298 (5)	0.0065 (4)	0.0101 (4)	0.0091 (4)
O2	0.0738 (9)	0.1032 (12)	0.0425 (7)	−0.0292 (8)	0.0360 (6)	−0.0212 (7)
O3	0.1001 (10)	0.0466 (7)	0.0285 (5)	−0.0007 (7)	0.0169 (6)	−0.0144 (5)
N1	0.0505 (7)	0.0419 (7)	0.0239 (5)	0.0073 (6)	0.0106 (5)	−0.0050 (5)
C1	0.0250 (5)	0.0196 (5)	0.0222 (5)	0.0009 (4)	0.0059 (4)	0.0023 (4)
C2	0.0227 (5)	0.0199 (5)	0.0194 (5)	−0.0018 (4)	0.0059 (4)	0.0002 (4)
C3	0.0206 (5)	0.0219 (5)	0.0185 (5)	−0.0005 (4)	0.0056 (4)	0.0006 (4)
C11	0.0246 (5)	0.0210 (5)	0.0214 (5)	0.0035 (4)	0.0055 (4)	0.0027 (4)
C12	0.0244 (6)	0.0290 (6)	0.0265 (6)	0.0013 (5)	0.0064 (4)	0.0031 (5)
C13	0.0318 (6)	0.0419 (7)	0.0296 (6)	0.0041 (6)	0.0144 (5)	0.0068 (6)
C14	0.0405 (7)	0.0497 (8)	0.0218 (6)	0.0089 (6)	0.0091 (5)	0.0023 (6)
C15	0.0335 (7)	0.0455 (8)	0.0248 (6)	0.0003 (6)	0.0007 (5)	−0.0029 (6)
C16	0.0258 (6)	0.0320 (6)	0.0276 (6)	−0.0006 (5)	0.0052 (5)	0.0021 (5)
C21	0.0237 (5)	0.0190 (5)	0.0197 (5)	0.0025 (4)	0.0050 (4)	0.0000 (4)
C22	0.0267 (6)	0.0241 (6)	0.0237 (5)	0.0019 (4)	0.0085 (4)	0.0000 (4)
C23	0.0355 (6)	0.0259 (6)	0.0213 (6)	0.0055 (5)	0.0073 (5)	−0.0017 (5)
C24	0.0373 (7)	0.0256 (6)	0.0280 (6)	−0.0008 (5)	−0.0004 (5)	−0.0050 (5)
C25	0.0284 (6)	0.0266 (6)	0.0354 (7)	−0.0052 (5)	0.0050 (5)	−0.0005 (5)
C26	0.0263 (6)	0.0244 (6)	0.0260 (6)	−0.0003 (4)	0.0076 (4)	0.0009 (5)

Geometric parameters (Å, º) top

O1—C1	1.2141 (15)	C13—H13	0.9500
O2—N1	1.2210 (19)	C14—C15	1.383 (2)
O3—N1	1.2199 (16)	C14—H14	0.9500
N1—C23	1.4676 (17)	C15—C16	1.3850 (18)
C1—C11	1.4957 (16)	C15—H15	0.9500
C1—C2	1.5104 (15)	C16—H16	0.9500
C2—C3	1.5412 (15)	C21—C22	1.3917 (16)
C2—C3ⁱ	1.5827 (16)	C21—C26	1.3938 (17)
C2—H2	1.0000	C22—C23	1.3810 (17)
C3—C21	1.5032 (15)	C22—H22	0.9500
C3—C2ⁱ	1.5827 (16)	C23—C24	1.380 (2)
C3—H3	1.0000	C24—C25	1.382 (2)
C11—C16	1.3910 (16)	C24—H24	0.9500
C11—C12	1.3931 (17)	C25—C26	1.3895 (17)
C12—C13	1.3877 (17)	C25—H25	0.9500
C12—H12	0.9500	C26—H26	0.9500
C13—C14	1.385 (2)

O3—N1—O2	123.53 (13)	C15—C14—C13	120.16 (12)
O3—N1—C23	118.42 (13)	C15—C14—H14	119.9
O2—N1—C23	118.05 (12)	C13—C14—H14	119.9
O1—C1—C11	120.53 (10)	C14—C15—C16	119.85 (12)
O1—C1—C2	122.11 (10)	C14—C15—H15	120.1
C11—C1—C2	117.32 (10)	C16—C15—H15	120.1
C1—C2—C3	115.82 (9)	C15—C16—C11	120.46 (12)
C1—C2—C3ⁱ	115.26 (9)	C15—C16—H16	119.8
C3—C2—C3ⁱ	90.93 (8)	C11—C16—H16	119.8
C1—C2—H2	111.1	C22—C21—C26	118.37 (10)
C3—C2—H2	111.1	C22—C21—C3	118.42 (10)
C3ⁱ—C2—H2	111.1	C26—C21—C3	123.13 (10)
C21—C3—C2	118.37 (9)	C23—C22—C21	119.39 (12)
C21—C3—C2ⁱ	116.97 (9)	C23—C22—H22	120.3
C2—C3—C2ⁱ	89.07 (8)	C21—C22—H22	120.3
C21—C3—H3	110.3	C24—C23—C22	122.92 (12)
C2—C3—H3	110.3	C24—C23—N1	119.20 (11)
C2ⁱ—C3—H3	110.3	C22—C23—N1	117.87 (12)
C16—C11—C12	119.38 (11)	C23—C24—C25	117.54 (11)
C16—C11—C1	118.23 (11)	C23—C24—H24	121.2
C12—C11—C1	122.39 (10)	C25—C24—H24	121.2
C13—C12—C11	119.94 (11)	C24—C25—C26	120.79 (12)
C13—C12—H12	120.0	C24—C25—H25	119.6
C11—C12—H12	120.0	C26—C25—H25	119.6
C14—C13—C12	120.16 (12)	C25—C26—C21	120.99 (11)
C14—C13—H13	119.9	C25—C26—H26	119.5
C12—C13—H13	119.9	C21—C26—H26	119.5

O1—C1—C2—C3	3.75 (16)	C1—C11—C16—C15	−179.34 (12)
C11—C1—C2—C3	−174.02 (9)	C2—C3—C21—C22	153.77 (10)
O1—C1—C2—C3ⁱ	108.12 (13)	C2ⁱ—C3—C21—C22	−101.51 (12)
C11—C1—C2—C3ⁱ	−69.65 (13)	C2—C3—C21—C26	−29.57 (16)
C1—C2—C3—C21	−120.73 (11)	C2ⁱ—C3—C21—C26	75.16 (14)
C3ⁱ—C2—C3—C21	120.45 (11)	C26—C21—C22—C23	0.10 (17)
C1—C2—C3—C2ⁱ	118.82 (11)	C3—C21—C22—C23	176.93 (11)
C3ⁱ—C2—C3—C2ⁱ	0.0	C21—C22—C23—C24	0.70 (19)
O1—C1—C11—C16	−28.05 (17)	C21—C22—C23—N1	179.91 (11)
C2—C1—C11—C16	149.76 (11)	O3—N1—C23—C24	11.86 (19)
O1—C1—C11—C12	152.23 (12)	O2—N1—C23—C24	−167.48 (14)
C2—C1—C11—C12	−29.96 (16)	O3—N1—C23—C22	−167.39 (13)
C16—C11—C12—C13	1.65 (18)	O2—N1—C23—C22	13.3 (2)
C1—C11—C12—C13	−178.63 (12)	C22—C23—C24—C25	−0.62 (19)
C11—C12—C13—C14	−2.1 (2)	N1—C23—C24—C25	−179.82 (12)
C12—C13—C14—C15	0.5 (2)	C23—C24—C25—C26	−0.24 (19)
C13—C14—C15—C16	1.5 (2)	C24—C25—C26—C21	1.03 (19)
C14—C15—C16—C11	−2.0 (2)	C22—C21—C26—C25	−0.94 (18)
C12—C11—C16—C15	0.39 (19)	C3—C21—C26—C25	−177.61 (11)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1	1.00	2.40	2.8509 (14)	106
C3—H3···O1ⁱⁱ	1.00	2.56	3.3957 (15)	141
C14—H14···O2ⁱⁱⁱ	0.95	2.56	3.3666 (19)	142
C2—H2···O3^iv	1.00	2.61	3.5009 (17)	148

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

Experimental details

Crystal data
Chemical formula	C₃₀H₂₂N₂O₆
M_r	506.50
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	200
a, b, c (Å)	5.7850 (1), 14.7824 (3), 14.3589 (3)
β (°)	104.858 (1)
V (Å³)	1186.86 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.33 × 0.14 × 0.11

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.968, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	11005, 2945, 2387
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.670

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.111, 1.03
No. of reflections	2945
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.22

Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012) and Mercury (Macrae et al., 2008), 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
C3—H3···O1ⁱ	1.00	2.56	3.3957 (15)	141
C14—H14···O2ⁱⁱ	0.95	2.56	3.3666 (19)	142
C2—H2···O3ⁱⁱⁱ	1.00	2.61	3.5009 (17)	148

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

Acknowledgements

BN thanks the UGC for financial assistance through a BSR one-time grant for the purchase of chemicals. PSN thanks Mangalore University for research facilities and the DST–PURSE for financial assistance.

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