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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 10| October 2012| Page o3008
https://doi.org/10.1107/S1600536812039700

3-Chloro­methyl-6,7-di­methyl-1,2-benz­oxazole

M. Kayalvizhi,a G. Vasuki,a* A. Veerareddyb and G. Laxminarasimhab

aDepartment of Physics, Kunthavai Naachiar Government Arts College (W) (Autonomous), Thanjavur 613 007, India, and bResearch and Development Laboratories, Suven Life Sciences Limited, Hyderabad 55, Andhra Pradesh, India
*Correspondence e-mail: vasuki.arasi@yahoo.com

(Received 29 August 2012; accepted 18 September 2012; online 26 September 2012)

In the title compound, C10H10ClNO, the benzoisoxazole ring is almost planar (r.m.s. deviation = 0.0121 Å) and the chloro substituent in the side chain is anti­clinal relative to the N—C bond of the isoxazole ring. In the crystal, adjacent mol­ecules are linked via a pair of weak C—H⋯N hydrogen bonds, forming dimers through a cyclic R22(8) association.

Related literature

For the biological and chemical applications of benzoxazoles, see: Ha et al. (2010[Ha, K., Lim, H. S. & Kim, H. J. (2010). Acta Cryst. E66, o2483.]); Kayalvizhi et al. (2011[Kayalvizhi, M., Vasuki, G., Ramamurthi, K., Veerareddy, A. & Laxmi­nara­simha, G. (2011). Acta Cryst. E67, o2999.]); Krishnaiah et al. (2009[Krishnaiah, M., Ravi Kumar, R., Oo, T. & Kaung, P. (2009). Acta Cryst. E65, o2324.]); Qu et al. (2008[Qu, Y., Zhang, S., Teng, L., Xia, X. & Zhang, Y. (2008). Acta Cryst. E64, o1210.]); Raju et al. (2002[Raju, K. V. N., Krishnaiah, M., Kumar, N. J. & Rao, S. N. (2002). Acta Cryst. A58, C128.]); Veerareddy et al. (2011[Veerareddy, A., Laxminarasimha, G., Uday, B. R. S. & Pramod, K. D. (2011). Indian J. Chem. Sect. B, 50, 119-125.]). For graph-set analysis, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. pp. 1555-1573.]).

[Scheme 1]

Experimental

Crystal data

  • C10H10ClNO

  • Mr = 195.64

  • Monoclinic, C 2/c

  • a = 20.4938 (15) Å

  • b = 4.1237 (3) Å

  • c = 24.6361 (18) Å

  • β = 114.151 (3)°

  • V = 1899.8 (2) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.36 mm−1

  • T = 295 K

  • 0.20 × 0.15 × 0.15 mm
Data collection

  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1999[Bruker (1999). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.932, Tmax = 0.948

  • 8155 measured reflections

  • 1748 independent reflections

  • 1396 reflections with I > 2σ(I)

  • Rint = 0.035
Refinement

  • R[F2 > 2σ(F2)] = 0.041

  • wR(F2) = 0.120

  • S = 1.06

  • 1748 reflections

  • 120 parameters

  • H-atom parameters constrained

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.19 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C10—H10B⋯N2i 0.97 2.55 3.479 (3) 160
Symmetry code: (i) [-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812039700/zs2231sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812039700/zs2231Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812039700/zs2231Isup3.cml

checkCIF report


Comment top

The benzoxazole ring system is one of the most common heterocycles in medicinal chemistry (Qu et al., 2008). Isoxazole derivatives bearing various substituents are known to have diverse biological activities in pharmaceutical and agricultural areas (Ha et al., 2010). In agriculture applications herbicidal activity has been identified (Raju et al., 2002) as well as fungicidal activities against some plant pathogens (Ha et al., 2010). Some derivatives are also used as semiconductors and as corrosion inhibitors in fuels and lubricants (Raju et al., 2002). They are also important intermediates in the synthesis of many complex natural products (Krishnaiah et al., 2009). Among these compounds, 3-substituted-1,2-benzisoxazole and its derivatives are emerging as potential antipsychotic compounds (Kayalvizhi et al., 2011). Substituted benzoxazoles have been reported to possess diverse chemotherapeutic properties including antibiotic, antimicrobial, antiviral, antitumor and other pharmacological activities (Qu et al., 2008; Krishnaiah et al., 2009). With its extensive uses as a drug for epilepsy, its cost-effective synthesis remained a great challenge for synthetic organic chemists (Veerareddy et al., 2011). In a search for new benzisoxazole compounds with better biological activity, the title compound, C10H10ClNO, was synthesized and its crystal structure determined, in order to examine the structure–activity effects of the chloromethyl and 6,7-dimethyl substituents on the benzoisoxazole ring.

In the structure of the title compound (Fig. 1) the benzoisoxazole ring is planar with a root mean square deviation of 0.0121 Å. The torsion angle [N2—C3—C10—Cl = 121.31 (19)°] indicates that the side chain is anticlinal looking down the C3—C10 bond. The exocyclic angles C10—C3—C3a [129.35 (19)°] and C3—C3a—C4 [137.13 (19)°] deviate significantly from the normal values and this may be due to the intramolecular non-bonded interaction between the chlorine atom and an aromatic H atom [Cl···H4 = 3.2582 (8) Å]. In the crystal, adjacent molecules are linked via a pair of weak intermolecular C—H···N hydrogen bonds (Table 1) forming dimers through a cyclic R22(8) association (Bernstein et al., 1995) (Fig. 2).

Related literature top

For the biological and chemical applications of benzoxazoles [Amended text OK?], see: Ha et al. (2010); Kayalvizhi et al. (2011); Krishnaiah et al. (2009); Qu et al. (2008); Raju et al. (2002); Veerareddy et al. (2011). For graph-set analysis, see: Bernstein et al. (1995).

Experimental top

To a solution of 3,6,7-trimethylbenzo[d]isoxazole-2-oxide (1.0 mol) in methylene dichloride (10 ml) was added POCl3 (2.0 mol) dropwise at 20°C over a period of 5 min and stirred for 5 min also at 20°C. Triethylamine (2.0 mol) was then added dropwise at 20°C over a period of 10 min at such a rate that the reaction temperature did not exceed 30°C. The mixture was then stirred at reflux temperature for 48 h and cooled to 10°C. The reaction mixture was washed with chilled water, followed by addition of a 10% Na2CO3 solution to obtain a neutral pH. The aqueous layer was re-extracted with methylene chloride (2 × 100 ml). The combined organic layer was dried over anhydrous Na2SO4 and the solvent was removed under vacuum to give the crude product, which was purified by column chromatography and by crystallization (Veerareddy et al., 2011).

Refinement top

All the H atoms were positioned geometrically and treated as riding on their parent atoms, with C—H = 0.93 Å (aromatic), 0.96 Å (methyl) and 0.97 Å (methylene), and refined using a riding model with Uiso(H) = 1.2Ueq or 1.5Ueq(parent atom).

Structure description top

The benzoxazole ring system is one of the most common heterocycles in medicinal chemistry (Qu et al., 2008). Isoxazole derivatives bearing various substituents are known to have diverse biological activities in pharmaceutical and agricultural areas (Ha et al., 2010). In agriculture applications herbicidal activity has been identified (Raju et al., 2002) as well as fungicidal activities against some plant pathogens (Ha et al., 2010). Some derivatives are also used as semiconductors and as corrosion inhibitors in fuels and lubricants (Raju et al., 2002). They are also important intermediates in the synthesis of many complex natural products (Krishnaiah et al., 2009). Among these compounds, 3-substituted-1,2-benzisoxazole and its derivatives are emerging as potential antipsychotic compounds (Kayalvizhi et al., 2011). Substituted benzoxazoles have been reported to possess diverse chemotherapeutic properties including antibiotic, antimicrobial, antiviral, antitumor and other pharmacological activities (Qu et al., 2008; Krishnaiah et al., 2009). With its extensive uses as a drug for epilepsy, its cost-effective synthesis remained a great challenge for synthetic organic chemists (Veerareddy et al., 2011). In a search for new benzisoxazole compounds with better biological activity, the title compound, C10H10ClNO, was synthesized and its crystal structure determined, in order to examine the structure–activity effects of the chloromethyl and 6,7-dimethyl substituents on the benzoisoxazole ring.

In the structure of the title compound (Fig. 1) the benzoisoxazole ring is planar with a root mean square deviation of 0.0121 Å. The torsion angle [N2—C3—C10—Cl = 121.31 (19)°] indicates that the side chain is anticlinal looking down the C3—C10 bond. The exocyclic angles C10—C3—C3a [129.35 (19)°] and C3—C3a—C4 [137.13 (19)°] deviate significantly from the normal values and this may be due to the intramolecular non-bonded interaction between the chlorine atom and an aromatic H atom [Cl···H4 = 3.2582 (8) Å]. In the crystal, adjacent molecules are linked via a pair of weak intermolecular C—H···N hydrogen bonds (Table 1) forming dimers through a cyclic R22(8) association (Bernstein et al., 1995) (Fig. 2).

For the biological and chemical applications of benzoxazoles [Amended text OK?], see: Ha et al. (2010); Kayalvizhi et al. (2011); Krishnaiah et al. (2009); Qu et al. (2008); Raju et al. (2002); Veerareddy et al. (2011). For graph-set analysis, see: Bernstein et al. (1995).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound showing atom numbering, with displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. The crystal packing of the title compound in the unit cell, viewed down the b axis, showing the molecular dimers.
3-Chloromethyl-6,7-dimethyl-1,2-benzoxazole top
Crystal data top
C10H10ClNOF(000) = 816
Mr = 195.64Dx = 1.368 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3599 reflections
a = 20.4938 (15) Åθ = 2.2–25.7°
b = 4.1237 (3) ŵ = 0.36 mm−1
c = 24.6361 (18) ÅT = 295 K
β = 114.151 (3)°Block, colourless
V = 1899.8 (2) Å30.20 × 0.15 × 0.15 mm
Z = 8
Data collection top
Bruker Kappa APEXII CCD
diffractometer		1748 independent reflections
Radiation source: fine-focus sealed tube1396 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
ω and φ scansθmax = 25.5°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 1999)		h = −24→24
Tmin = 0.932, Tmax = 0.948k = −4→4
8155 measured reflectionsl = −29→29
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0575P)2 + 1.2791P]
where P = (Fo2 + 2Fc2)/3
1748 reflections(Δ/σ)max < 0.001
120 parametersΔρmax = 0.25 e Å−3
0 restraintsΔρmin = −0.19 e Å−3
Crystal data top
C10H10ClNOV = 1899.8 (2) Å3
Mr = 195.64Z = 8
Monoclinic, C2/cMo Kα radiation
a = 20.4938 (15) ŵ = 0.36 mm−1
b = 4.1237 (3) ÅT = 295 K
c = 24.6361 (18) Å0.20 × 0.15 × 0.15 mm
β = 114.151 (3)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer		1748 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1999)		1396 reflections with I > 2σ(I)
Tmin = 0.932, Tmax = 0.948Rint = 0.035
8155 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.120H-atom parameters constrained
S = 1.06Δρmax = 0.25 e Å−3
1748 reflectionsΔρmin = −0.19 e Å−3
120 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. 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 > 2sigma(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
xyzUiso*/Ueq
Cl0.36216 (3)0.4407 (2)0.14499 (3)0.0810 (3)
O10.11696 (8)0.2766 (4)0.03641 (6)0.0579 (4)
C3A0.19031 (10)0.5502 (5)0.11668 (8)0.0449 (4)
C40.20916 (11)0.6941 (5)0.17240 (9)0.0535 (5)
H40.25300.79720.19190.064*
C70.07354 (10)0.3861 (5)0.11299 (8)0.0490 (5)
C7A0.12460 (10)0.4049 (5)0.08966 (8)0.0464 (5)
C60.09376 (11)0.5243 (5)0.16895 (9)0.0529 (5)
C30.22228 (11)0.5014 (5)0.07591 (9)0.0492 (5)
C50.16064 (12)0.6770 (5)0.19698 (9)0.0560 (5)
H50.17230.77080.23410.067*
N20.18083 (10)0.3418 (5)0.02923 (8)0.0610 (5)
C80.00258 (12)0.2276 (6)0.07915 (10)0.0667 (6)
H8A−0.00580.06680.10380.100*
H8B0.00260.12610.04410.100*
H8C−0.03450.38820.06790.100*
C100.29367 (12)0.6064 (6)0.08013 (10)0.0620 (6)
H10A0.29660.84130.08160.074*
H10B0.30010.53440.04520.074*
C90.04460 (14)0.5113 (7)0.20055 (11)0.0761 (7)
H9A−0.00060.60700.17590.114*
H9B0.06560.62890.23730.114*
H9C0.03740.28950.20860.114*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl0.0488 (4)0.1014 (6)0.0848 (5)0.0015 (3)0.0190 (3)0.0112 (4)
O10.0509 (8)0.0716 (10)0.0462 (7)−0.0017 (7)0.0147 (6)−0.0086 (7)
C3A0.0457 (10)0.0404 (10)0.0441 (10)0.0069 (8)0.0137 (8)0.0031 (8)
C40.0503 (11)0.0513 (12)0.0505 (11)0.0030 (9)0.0123 (9)−0.0051 (9)
C70.0434 (10)0.0489 (12)0.0491 (11)0.0097 (9)0.0134 (9)0.0077 (9)
C7A0.0471 (10)0.0449 (11)0.0403 (9)0.0087 (8)0.0107 (8)0.0016 (8)
C60.0528 (12)0.0534 (12)0.0510 (11)0.0142 (9)0.0196 (9)0.0066 (9)
C30.0498 (11)0.0469 (11)0.0497 (11)0.0075 (9)0.0191 (9)0.0045 (9)
C50.0624 (13)0.0571 (13)0.0445 (10)0.0093 (10)0.0178 (10)−0.0053 (9)
N20.0569 (11)0.0739 (13)0.0522 (10)0.0036 (9)0.0225 (9)−0.0040 (9)
C80.0487 (12)0.0770 (16)0.0676 (14)−0.0030 (11)0.0170 (10)0.0022 (12)
C100.0605 (13)0.0608 (14)0.0678 (14)0.0006 (11)0.0295 (11)0.0058 (11)
C90.0754 (16)0.0931 (19)0.0708 (15)0.0116 (14)0.0411 (13)0.0039 (13)
Geometric parameters (Å, º) top
Cl—C101.776 (2)C6—C91.505 (3)
O1—C7A1.363 (2)C3—N21.295 (3)
O1—N21.417 (2)C3—C101.488 (3)
C3A—C7A1.372 (3)C5—H50.9300
C3A—C41.397 (3)C8—H8A0.9600
C3A—C31.420 (3)C8—H8B0.9600
C4—C51.361 (3)C8—H8C0.9600
C4—H40.9300C10—H10A0.9700
C7—C7A1.387 (3)C10—H10B0.9700
C7—C61.389 (3)C9—H9A0.9600
C7—C81.498 (3)C9—H9B0.9600
C6—C51.406 (3)C9—H9C0.9600
C7A—O1—N2107.37 (15)C6—C5—H5118.4
C7A—C3A—C4118.97 (18)C3—N2—O1106.82 (16)
C7A—C3A—C3103.89 (17)C7—C8—H8A109.5
C4—C3A—C3137.13 (19)C7—C8—H8B109.5
C5—C4—C3A117.15 (19)H8A—C8—H8B109.5
C5—C4—H4121.4C7—C8—H8C109.5
C3A—C4—H4121.4H8A—C8—H8C109.5
C7A—C7—C6114.78 (18)H8B—C8—H8C109.5
C7A—C7—C8121.25 (18)C3—C10—Cl110.08 (15)
C6—C7—C8123.97 (19)C3—C10—H10A109.6
O1—C7A—C3A109.88 (17)Cl—C10—H10A109.6
O1—C7A—C7124.63 (18)C3—C10—H10B109.6
C3A—C7A—C7125.48 (18)Cl—C10—H10B109.6
C7—C6—C5120.40 (19)H10A—C10—H10B108.2
C7—C6—C9120.5 (2)C6—C9—H9A109.5
C5—C6—C9119.09 (19)C6—C9—H9B109.5
N2—C3—C3A112.04 (18)H9A—C9—H9B109.5
N2—C3—C10118.61 (19)C6—C9—H9C109.5
C3A—C3—C10129.35 (19)H9A—C9—H9C109.5
C4—C5—C6123.19 (19)H9B—C9—H9C109.5
C4—C5—H5118.4
C7A—C3A—C4—C50.8 (3)C7A—C7—C6—C9−177.88 (19)
C3—C3A—C4—C5−178.2 (2)C8—C7—C6—C92.2 (3)
N2—O1—C7A—C3A0.2 (2)C7A—C3A—C3—N2−0.4 (2)
N2—O1—C7A—C7−178.95 (17)C4—C3A—C3—N2178.7 (2)
C4—C3A—C7A—O1−179.26 (17)C7A—C3A—C3—C10179.5 (2)
C3—C3A—C7A—O10.1 (2)C4—C3A—C3—C10−1.4 (4)
C4—C3A—C7A—C7−0.1 (3)C3A—C4—C5—C6−0.2 (3)
C3—C3A—C7A—C7179.25 (18)C7—C6—C5—C4−1.2 (3)
C6—C7—C7A—O1177.83 (18)C9—C6—C5—C4178.5 (2)
C8—C7—C7A—O1−2.3 (3)C3A—C3—N2—O10.5 (2)
C6—C7—C7A—C3A−1.2 (3)C10—C3—N2—O1−179.36 (17)
C8—C7—C7A—C3A178.7 (2)C7A—O1—N2—C3−0.5 (2)
C7A—C7—C6—C51.8 (3)N2—C3—C10—Cl−121.31 (19)
C8—C7—C6—C5−178.1 (2)C3A—C3—C10—Cl58.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10B···N2i0.972.553.479 (3)160
Symmetry code: (i) −x+1/2, −y+1/2, −z.

Experimental details

Crystal data
Chemical formulaC10H10ClNO
Mr195.64
Crystal system, space groupMonoclinic, C2/c
Temperature (K)295
a, b, c (Å)20.4938 (15), 4.1237 (3), 24.6361 (18)
β (°) 114.151 (3)
V (Å3)1899.8 (2)
Z8
Radiation typeMo Kα
µ (mm−1)0.36
Crystal size (mm)0.20 × 0.15 × 0.15
Data collection
DiffractometerBruker Kappa APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 1999)
Tmin, Tmax0.932, 0.948
No. of measured, independent and
observed [I > 2σ(I)] reflections		8155, 1748, 1396
Rint0.035
(sin θ/λ)max (Å−1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.120, 1.06
No. of reflections1748
No. of parameters120
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.25, −0.19

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10B···N2i0.972.553.479 (3)160
Symmetry code: (i) −x+1/2, −y+1/2, −z.
 

Acknowledgements

The authors thank the Sophisticated Analytical Instrument Facility, IIT-Madras, Chennai, for the single-crystal X-ray data collection.

References

First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. pp. 1555–1573.  CrossRef Web of Science Google Scholar
 First citationBruker (1999). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationBruker (2004). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationHa, K., Lim, H. S. & Kim, H. J. (2010). Acta Cryst. E66, o2483.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationKayalvizhi, M., Vasuki, G., Ramamurthi, K., Veerareddy, A. & Laxmi­nara­simha, G. (2011). Acta Cryst. E67, o2999.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationKrishnaiah, M., Ravi Kumar, R., Oo, T. & Kaung, P. (2009). Acta Cryst. E65, o2324.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationQu, Y., Zhang, S., Teng, L., Xia, X. & Zhang, Y. (2008). Acta Cryst. E64, o1210.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationRaju, K. V. N., Krishnaiah, M., Kumar, N. J. & Rao, S. N. (2002). Acta Cryst. A58, C128.  CrossRef IUCr Journals Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationVeerareddy, A., Laxminarasimha, G., Uday, B. R. S. & Pramod, K. D. (2011). Indian J. Chem. Sect. B, 50, 119–125.  Google Scholar

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ISSN: 2056-9890
Volume 68| Part 10| October 2012| Page o3008
https://doi.org/10.1107/S1600536812039700
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