Crystal structure of 3-[4-(pyrimidin-2-yl)piperazin-1-ium-1-yl]butano­ate

Yamuna, T.S.; Jasinski, J.P.; Kaur, M.; Anderson, B.J.; Yathirajan, H.S.

doi:10.1107/S1600536814018972

organic compounds

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Volume 70| Part 9| September 2014| Pages o1063-o1064

doi:10.1107/S1600536814018972

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Crystal structure of 3-[4-(pyrimidin-2-yl)piperazin-1-ium-1-yl]butanoate

Thammarse S. Yamuna,^a Jerry P. Jasinski,^b ^* Manpreet Kaur,^a Brian J. Anderson ^b and H.S. Yathirajan ^a

^aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and ^bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
^*Correspondence e-mail: jjasinski@keene.edu

Edited by M. Bolte, Goethe-Universität Frankfurt Germany (Received 15 August 2014; accepted 21 August 2014; online 30 August 2014)

The title compound, C₁₂H₁₈N₄O₂, crystallizes in the zwitterionic form with protonation at the N atom of the piperazine ring bearing the carboxylate group. The piperazine ring adopts a slightly distorted chair conformation. In the crystal, N—H⋯O hydrogen bonds are observed, forming chains along [010]. The packing is consolidated by C—H⋯O interactions, which generate a three-dimensional network.

Keywords: crystal structure; 3-(piperazin-1-ium-1-yl)butanoate; zwitterionic form; fused heterocyclic derivatives; aza-Michael reactions.

CCDC reference: 1020635

1. Related literature

For general background and pharmacological properties of fused heterocyclic derivatives, see: Amin et al. (2009 ); Ibrahim & El-Metwally (2010 ); Kuyper et al. (1996 ); Onal & Yıldırım (2007 ); Padmaja et al. (2009 ); Tollefson et al. (1991 ). For pharmacological properties of pyrimidines, see: Burdge (2000 ). For background to aza-Michael reactions, see: Arend et al.(1998 ); Vicario et al. (2005 ); Xu & Xia (2005 ). For related structures, see: Jin et al. (2012 ); Parvez et al. (2004 ); Yamuna et al. (2014a ,b ).

2. Experimental

2.1. Crystal data

C₁₂H₁₈N₄O₂
M_r = 250.30
Monoclinic, P 2₁ /c
a = 13.5157 (6) Å
b = 7.8454 (3) Å
c = 12.2147 (5) Å
β = 106.884 (5)°
V = 1239.36 (9) Å³
Z = 4
Cu Kα radiation
μ = 0.77 mm⁻¹
T = 173 K
0.32 × 0.22 × 0.06 mm

2.1.2. Data collection

Agilent Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012 ) T_min = 0.854, T_max = 1.000
3995 measured reflections
3995 independent reflections
3668 reflections with I > 2σ(I)

2.1.3. Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.149
S = 1.06
3995 reflections
169 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	1.00	1.67	2.653 (2)	168
C2—H2B⋯O2ⁱ	0.99	2.51	3.277 (3)	134
C4—H4B⋯O1ⁱⁱ	0.99	2.58	3.428 (3)	144
C7—H7B⋯O1ⁱ	0.99	2.53	3.147 (3)	120
C11—H11⋯O1ⁱⁱⁱ	0.95	2.47	3.352 (3)	155
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x, -y+1, -z+1; (iii) $[x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED; program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007 ); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008 ); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: OLEX2.

Supporting information

CCDC reference: 1020635

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814018972/bt6993sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814018972/bt6993Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814018972/bt6993Isup3.cml

checkCIF report

Comment top

Pyrimidines in general have been of much interest for biological and medical reasons and thus their chemistry has been investigated extensively (Onal & Yıldırım, 2007) and in many drugs used for the treatment of hypothyroidism and hypertension, in cancer chemotherapy or HIV infections (Burdge, 2000) and with related fused heterocyclic compounds that exhibit biological activities such as anticancer (Amin et al., 2009), antiviral (Ibrahim & El-Metwally, 2010), antibacterial (Kuyper et al., 1996) and antioxidant (Padmaja et al., 2009). Some pyrimidinylpiperazinyl compounds like buspirone and BuSpar (Tollefson et al., 1991) are used to treat anxiety. The incorporation of two moieties increases biological activity of both the molecules. Aza-Michael addition reaction has been extensively studied using a variety of catalysts as well as solvents and various researchers have also reported the utility of aza-Michael addition towards the synthesis of various pharmacological active compounds and proved useful in the synthesis of core intermediates of many natural products (Arend et al., 1998). The role of aza-Michael reaction in the synthesis of pharmacologically important families of β-amino carbonyl compounds and its derivatives is well documented in the literature (Vicario et al., 2005; Xu & Xia, 2005). Our research group has published many papers on incorporated heterocyclic ring structures, viz; 4-(pyrimidin-2-yl)piperazin-1-ium (E)-3-carboxyprop-2-enoate (Yamuna et al., 2014a); flupentixol tartarate (Yamuna et al., 2014b). Some related zwitterion structures are: 3,3'-(piperazine-1,4-diium-1,4-diyl)dipropionate dihydrate (Jin et al., 2012), enoxacin trihydrate[1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(piperazin-4-ium-1-yl)-1,8- naphthyridine-3-carboxylate trihydrate] (Parvez et al., 2004). In view of the importance of derivatives of the incorporated heterocyclic pyrimidylpiperazines, this paper reports the crystal structure of the title zwitterionic compound, (I), 3-(4-Pyrimidin-2-yl-piperazin-1-ium-1-yl)-butanoate, C₁₂H₁₈N₄O₂ prepared from 2-(piperazin-1-yl)pyrimidine and but-2-enoic acid by aza-Michael addition reaction.

The title compound, (I), C₁₂H₁₈N₄O₂ crystallizes in the zwitterionic form with protonation on the N1 nitrogen atom of the piperazine ring (Fig. 1). In the compound, the piperazine ring adopts a slightly disordered chair conformation (puckering parameters Q, θ, and ϕ = 0.576 (2)Å, 3.0 (2)° and 282 (4)°, respectively. Bond lengths are in normal ranges. In the crystal, N—H···O intermolecular hydrogen bonds are observed forming 1D chains along [0 1 0] (Fig. 2). The packing is consolidated by weak C—H···O interactions which generate a three-dimensional network.

Related literature top

For general background and pharmacological properties of fused heterocyclic derivatives, see: Amin et al. (2009); Ibrahim & El-Metwally (2010); Kuyper et al. (1996); Onal & Yıldırım (2007); Padmaja et al. (2009); Tollefson et al. (1991). For pharmacological properties of pyrimidines, see: Burdge (2000). For the importance of aza-Michael reactions, see: Arend et al.(1998); Vicario et al. (2005); Xu & Xia (2005). For related structures, see: Jin et al. (2012); Parvez et al. (2004); Yamuna et al. (2014a,b).

Experimental top

A mixture of 1-(2-pyrimidyl)piperazine, from sigma-aldrich (0.2 g, 1.22 mmol) and crotonic acid (but-2-enoic acid) (0.1048 g, 1.22 mmol ) were dissolved in DMSO, stirred well and warmed at 343 K for 20 minutes. After few days, X-ray quality crystals were obtained on slow evaporation (m.p.: 411-418 K).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

	Fig. 1. ORTEP drawing of (C₁₂H₁₈N₄O₂) showing the labeling scheme of the asymmetric unit of the title compound with 30% probability displacement ellipsoids.
	Fig. 2. Molecular packing for (I), viewed along the b axis. Dashed lines indicate weak C—H···O intermolecular interactions in addition to N—H···O intermolecular hydrogen bonds which together form an extended three-dimensional supramolecular network structure. H atoms not involved in hydrogen bonding have been removed for clarity.

3-[4-(Pyrimidin-2-yl)piperazin-1-ium-1-yl]butanoate top

Crystal data top

C₁₂H₁₈N₄O₂	F(000) = 536
M_r = 250.30	D_x = 1.341 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
a = 13.5157 (6) Å	Cell parameters from 5404 reflections
b = 7.8454 (3) Å	θ = 3.8–71.4°
c = 12.2147 (5) Å	µ = 0.77 mm⁻¹
β = 106.884 (5)°	T = 173 K
V = 1239.36 (9) Å³	Irregular, colourless
Z = 4	0.32 × 0.22 × 0.06 mm

Data collection top

Agilent Eos Gemini diffractometer	3995 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3668 reflections with I > 2σ(I)
Detector resolution: 16.0416 pixels mm^-1	θ_max = 71.2°, θ_min = 3.4°
ω scans	h = −16→16
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	k = −9→9
T_min = 0.854, T_max = 1.000	l = −13→14
3995 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.053	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.149	w = 1/[σ²(F_o²) + (0.0768P)² + 0.6386P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
3995 reflections	Δρ_max = 0.36 e Å⁻³
169 parameters	Δρ_min = −0.27 e Å⁻³
0 restraints

Crystal data top

C₁₂H₁₈N₄O₂	V = 1239.36 (9) Å³
M_r = 250.30	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 13.5157 (6) Å	µ = 0.77 mm⁻¹
b = 7.8454 (3) Å	T = 173 K
c = 12.2147 (5) Å	0.32 × 0.22 × 0.06 mm
β = 106.884 (5)°

Data collection top

Agilent Eos Gemini diffractometer	3995 measured reflections
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012)	3995 independent reflections
T_min = 0.854, T_max = 1.000	3668 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.149	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.36 e Å⁻³
3995 reflections	Δρ_min = −0.27 e Å⁻³
169 parameters

Special details top

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. Refined as a 2-component twin.

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

	x	y	z	U_iso*/U_eq
O1	−0.15848 (13)	0.4680 (3)	0.29107 (16)	0.0449 (5)
O2	−0.05978 (12)	0.4109 (2)	0.17822 (15)	0.0339 (4)
N1	0.16438 (12)	0.1694 (2)	0.44116 (14)	0.0217 (4)
H1	0.1313	0.0618	0.4040	0.026*
N2	0.32869 (12)	0.0043 (3)	0.60849 (16)	0.0287 (4)
N3	0.40034 (14)	0.0836 (3)	0.79721 (17)	0.0324 (5)
N4	0.50457 (13)	0.0549 (3)	0.66957 (17)	0.0336 (5)
C1	−0.08258 (15)	0.4025 (3)	0.2726 (2)	0.0277 (5)
C2	−0.00940 (16)	0.2979 (3)	0.3691 (2)	0.0308 (5)
H2A	−0.0174	0.3357	0.4434	0.037*
H2B	−0.0296	0.1763	0.3588	0.037*
C3	0.10322 (15)	0.3150 (3)	0.3722 (2)	0.0260 (5)
H3	0.098 (2)	0.289 (4)	0.289 (3)	0.041 (8)*
C4	0.16425 (15)	0.1604 (3)	0.56333 (18)	0.0261 (5)
H4A	0.0922	0.1532	0.5671	0.031*
H4B	0.1959	0.2650	0.6040	0.031*
C5	0.22479 (15)	0.0048 (3)	0.6211 (2)	0.0290 (5)
H5A	0.2291	0.0053	0.7034	0.035*
H5B	0.1880	−0.1001	0.5866	0.035*
C6	0.32772 (15)	0.0092 (3)	0.48941 (19)	0.0276 (5)
H6A	0.2918	−0.0928	0.4491	0.033*
H6B	0.3995	0.0084	0.4845	0.033*
C7	0.27285 (14)	0.1685 (3)	0.43312 (18)	0.0243 (4)
H7A	0.3102	0.2707	0.4716	0.029*
H7B	0.2719	0.1716	0.3518	0.029*
C8	0.41389 (15)	0.0508 (3)	0.69526 (18)	0.0248 (4)
C9	0.48642 (19)	0.1182 (3)	0.8810 (2)	0.0359 (5)
H9	0.4802	0.1456	0.9545	0.043*
C10	0.58388 (18)	0.1162 (3)	0.8665 (2)	0.0372 (6)
H10	0.6444	0.1349	0.9284	0.045*
C11	0.58837 (17)	0.0857 (3)	0.7574 (2)	0.0376 (6)
H11	0.6540	0.0864	0.7436	0.045*
C12	0.14735 (18)	0.4895 (3)	0.4145 (2)	0.0329 (5)
H12A	0.1545	0.4997	0.4964	0.049*
H12B	0.1007	0.5784	0.3725	0.049*
H12C	0.2153	0.5026	0.4019	0.049*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0322 (9)	0.0605 (12)	0.0415 (11)	0.0190 (8)	0.0099 (8)	0.0110 (9)
O2	0.0282 (8)	0.0318 (8)	0.0409 (10)	0.0066 (6)	0.0087 (7)	0.0019 (7)
N1	0.0143 (7)	0.0280 (9)	0.0214 (9)	0.0003 (6)	0.0028 (6)	0.0038 (7)
N2	0.0138 (8)	0.0488 (11)	0.0234 (9)	0.0065 (7)	0.0053 (7)	0.0076 (8)
N3	0.0284 (9)	0.0427 (11)	0.0266 (10)	0.0100 (8)	0.0088 (8)	0.0026 (8)
N4	0.0184 (8)	0.0522 (12)	0.0303 (10)	0.0007 (8)	0.0070 (8)	−0.0065 (9)
C1	0.0200 (9)	0.0303 (11)	0.0295 (11)	−0.0011 (8)	0.0018 (8)	0.0025 (9)
C2	0.0222 (10)	0.0364 (12)	0.0335 (12)	0.0054 (9)	0.0078 (9)	0.0073 (10)
C3	0.0200 (9)	0.0287 (10)	0.0259 (10)	0.0018 (8)	0.0014 (8)	0.0052 (9)
C4	0.0166 (9)	0.0379 (12)	0.0245 (10)	0.0041 (8)	0.0072 (8)	0.0033 (9)
C5	0.0158 (9)	0.0441 (13)	0.0282 (11)	0.0042 (8)	0.0084 (8)	0.0112 (10)
C6	0.0169 (9)	0.0424 (13)	0.0233 (10)	0.0046 (8)	0.0059 (8)	0.0012 (9)
C7	0.0154 (9)	0.0373 (11)	0.0204 (10)	−0.0038 (8)	0.0055 (7)	0.0012 (9)
C8	0.0184 (9)	0.0304 (10)	0.0254 (11)	0.0077 (8)	0.0062 (8)	0.0044 (9)
C9	0.0359 (12)	0.0428 (13)	0.0264 (12)	0.0102 (10)	0.0051 (10)	−0.0020 (10)
C10	0.0297 (11)	0.0408 (13)	0.0336 (13)	0.0035 (10)	−0.0027 (10)	−0.0052 (10)
C11	0.0199 (10)	0.0495 (14)	0.0407 (14)	0.0000 (10)	0.0046 (9)	−0.0103 (11)
C12	0.0322 (11)	0.0287 (11)	0.0337 (13)	−0.0001 (9)	0.0032 (10)	0.0024 (10)

Geometric parameters (Å, º) top

O1—C1	1.226 (3)	C4—H4A	0.9900
O2—C1	1.278 (3)	C4—H4B	0.9900
N1—H1	1.0000	C4—C5	1.524 (3)
N1—C3	1.514 (2)	C5—H5A	0.9900
N1—C4	1.494 (3)	C5—H5B	0.9900
N1—C7	1.498 (2)	C6—H6A	0.9900
N2—C5	1.457 (2)	C6—H6B	0.9900
N2—C6	1.451 (3)	C6—C7	1.513 (3)
N2—C8	1.369 (3)	C7—H7A	0.9900
N3—C8	1.335 (3)	C7—H7B	0.9900
N3—C9	1.335 (3)	C9—H9	0.9500
N4—C8	1.351 (3)	C9—C10	1.379 (3)
N4—C11	1.336 (3)	C10—H10	0.9500
C1—C2	1.538 (3)	C10—C11	1.373 (4)
C2—H2A	0.9900	C11—H11	0.9500
C2—H2B	0.9900	C12—H12A	0.9800
C2—C3	1.518 (3)	C12—H12B	0.9800
C3—H3	1.01 (3)	C12—H12C	0.9800
C3—C12	1.523 (3)

C3—N1—H1	106.5	N2—C5—H5B	109.4
C4—N1—H1	106.5	C4—C5—H5A	109.4
C4—N1—C3	115.63 (17)	C4—C5—H5B	109.4
C4—N1—C7	110.51 (15)	H5A—C5—H5B	108.0
C7—N1—H1	106.5	N2—C6—H6A	109.7
C7—N1—C3	110.70 (15)	N2—C6—H6B	109.7
C6—N2—C5	112.18 (17)	N2—C6—C7	109.75 (18)
C8—N2—C5	122.52 (19)	H6A—C6—H6B	108.2
C8—N2—C6	121.99 (18)	C7—C6—H6A	109.7
C8—N3—C9	115.4 (2)	C7—C6—H6B	109.7
C11—N4—C8	115.6 (2)	N1—C7—C6	109.51 (16)
O1—C1—O2	125.4 (2)	N1—C7—H7A	109.8
O1—C1—C2	118.0 (2)	N1—C7—H7B	109.8
O2—C1—C2	116.65 (19)	C6—C7—H7A	109.8
C1—C2—H2A	109.0	C6—C7—H7B	109.8
C1—C2—H2B	109.0	H7A—C7—H7B	108.2
H2A—C2—H2B	107.8	N3—C8—N2	117.45 (18)
C3—C2—C1	112.91 (18)	N3—C8—N4	126.3 (2)
C3—C2—H2A	109.0	N4—C8—N2	116.26 (19)
C3—C2—H2B	109.0	N3—C9—H9	118.3
N1—C3—C2	109.19 (17)	N3—C9—C10	123.5 (2)
N1—C3—H3	105.9 (16)	C10—C9—H9	118.3
N1—C3—C12	113.11 (17)	C9—C10—H10	122.0
C2—C3—H3	100.5 (16)	C11—C10—C9	116.1 (2)
C2—C3—C12	112.28 (19)	C11—C10—H10	122.0
C12—C3—H3	115.0 (17)	N4—C11—C10	123.0 (2)
N1—C4—H4A	109.6	N4—C11—H11	118.5
N1—C4—H4B	109.6	C10—C11—H11	118.5
N1—C4—C5	110.12 (17)	C3—C12—H12A	109.5
H4A—C4—H4B	108.1	C3—C12—H12B	109.5
C5—C4—H4A	109.6	C3—C12—H12C	109.5
C5—C4—H4B	109.6	H12A—C12—H12B	109.5
N2—C5—C4	110.96 (17)	H12A—C12—H12C	109.5
N2—C5—H5A	109.4	H12B—C12—H12C	109.5

O1—C1—C2—C3	−144.6 (2)	C6—N2—C5—C4	−57.3 (3)
O2—C1—C2—C3	36.8 (3)	C6—N2—C8—N3	163.5 (2)
N1—C4—C5—N2	54.5 (2)	C6—N2—C8—N4	−18.1 (3)
N2—C6—C7—N1	−59.2 (2)	C7—N1—C3—C2	172.41 (18)
N3—C9—C10—C11	3.7 (4)	C7—N1—C3—C12	−61.8 (2)
C1—C2—C3—N1	−161.91 (18)	C7—N1—C4—C5	−55.5 (2)
C1—C2—C3—C12	71.8 (3)	C8—N2—C5—C4	102.5 (2)
C3—N1—C4—C5	177.77 (16)	C8—N2—C6—C7	−100.4 (2)
C3—N1—C7—C6	−172.54 (17)	C8—N3—C9—C10	−1.8 (4)
C4—N1—C3—C2	−61.0 (2)	C8—N4—C11—C10	−1.8 (4)
C4—N1—C3—C12	64.8 (2)	C9—N3—C8—N2	176.1 (2)
C4—N1—C7—C6	58.0 (2)	C9—N3—C8—N4	−2.2 (3)
C5—N2—C6—C7	59.5 (2)	C9—C10—C11—N4	−1.7 (4)
C5—N2—C8—N3	5.7 (3)	C11—N4—C8—N2	−174.3 (2)
C5—N2—C8—N4	−175.9 (2)	C11—N4—C8—N3	4.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	1.00	1.67	2.653 (2)	168
C2—H2B···O2ⁱ	0.99	2.51	3.277 (3)	134
C4—H4B···O1ⁱⁱ	0.99	2.58	3.428 (3)	144
C7—H7B···O1ⁱ	0.99	2.53	3.147 (3)	120
C11—H11···O1ⁱⁱⁱ	0.95	2.47	3.352 (3)	155

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	1.00	1.67	2.653 (2)	167.7
C2—H2B···O2ⁱ	0.99	2.51	3.277 (3)	133.8
C4—H4B···O1ⁱⁱ	0.99	2.58	3.428 (3)	143.5
C7—H7B···O1ⁱ	0.99	2.53	3.147 (3)	120.3
C11—H11···O1ⁱⁱⁱ	0.95	2.47	3.352 (3)	155.0

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

Acknowledgements

TSY thanks University of Mysore for research facilities and also grateful to the Principal, Maharani's Science College for Women, Mysore, for giving permission to do research. JPJ acknowledges the NSF–MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

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