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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 12| December 2010| Page m1680
https://doi.org/10.1107/S1600536810048890

Di­aqua­di­chloridobis[quinazolin-4(1H)-one-κN3]copper(II)

Kambarali Turgunov,a* Shirin Shomurotova,b Nasir Mukhamedova and Bakhodir Tashkhodjaeva

aS.Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of Uzbekistan, Mirzo Ulugbek Str. 77, Tashkent 100170, Uzbekistan, and bTashkent State Pedagogical University Named After Nizami, Yusuf Khos Khojib Str. 103, Tashkent 100100, Uzbekistan
*Correspondence e-mail: kk_turgunov@rambler.ru

(Received 16 November 2010; accepted 23 November 2010; online 27 November 2010)

In the title complex, [CuCl2(C8H6N2O)2(H2O)2], the CuII ion is located on an inversion center and is octahedrally coordinated by two N atoms of the 1H-quinazolin-4-one ligand, two chloride ligands and two aqua ligands. The axial Cu—O distances are significantly longer [2.512 (2) Å], than the Cu—N [2.022 (2) Å] and Cu—Cl [2.3232 (4) Å] distances as a result of Jahn–Teller distortion. Aqua ligands are involved in intra- and inter­molecular hydrogen bonding, and N—H⋯O inter­molecular hydrogen bonds are formed between the organic ligands. In addition, weak π–π inter­actions are observed between the benzene rings of the ligand [centroid–centroid distance = 3.678 (1) Å].

Related literature

The crystal structure of pyrimidin-4(3H)-one was reported by Vaillancourt et al. (1998[Vaillancourt, L., Simard, M. & Wuest, J. D. (1998). J. Org. Chem. 63, 9746-9752.]). For a Cd(II) coordination polymer with quinazolin-4(3H)-one, see: Turgunov & Englert (2010[Turgunov, K. & Englert, U. (2010). Acta Cryst. E66, m1457.]). For computational studies of quinazolin-4-one derivatives, see: Bakalova et al. (2004[Bakalova, S. M., Santos, A. G., Timcheva, I., Kaneti, J., Filipova, I. L., Dobrikov, G. M. & Dimitrov, V. D. (2004). J. Mol. Struct. (THEOCHEM), 710, 229-234.]).

[Scheme 1]

Experimental

Crystal data

  • [CuCl2(C8H6N2O)2(H2O)2]

  • Mr = 462.77

  • Monoclinic, P 21 /c

  • a = 6.7438 (3) Å

  • b = 18.5328 (8) Å

  • c = 6.7831 (3) Å

  • β = 90.735 (3)°

  • V = 847.69 (6) Å3

  • Z = 2

  • Cu Kα radiation

  • μ = 5.03 mm−1

  • T = 293 K

  • 0.55 × 0.35 × 0.20 mm
Data collection

  • Oxford Diffraction Xcalibur Ruby diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.366, Tmax = 1.000

  • 5548 measured reflections

  • 1725 independent reflections

  • 1639 reflections with I > 2σ(I)

  • Rint = 0.040
Refinement

  • R[F2 > 2σ(F2)] = 0.032

  • wR(F2) = 0.089

  • S = 1.10

  • 1725 reflections

  • 137 parameters

  • 3 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.37 e Å−3

  • Δρmin = −0.46 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O1W—H1W⋯O1i 0.84 (2) 1.92 (3) 2.732 (2) 162 (3)
O1W—H2W⋯Cl1ii 0.85 (2) 2.51 (2) 3.355 (2) 171 (4)
N1—H1⋯O1iii 0.84 (2) 2.39 (3) 3.022 (2) 133 (3)
N1—H1⋯Cl1iv 0.84 (2) 2.63 (3) 3.324 (2) 140 (3)
C2—H2A⋯O1W 0.93 2.38 2.972 (3) 121
C7—H7A⋯O1Wv 0.93 2.57 3.421 (3) 152
Symmetry codes: (i) -x, -y+1, -z+1; (ii) x, y, z-1; (iii) x+1, y, z; (iv) -x+1, -y+1, -z+1; (v) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2007[Oxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: XP (Bruker, 1998[Bruker (1998). XP. Bruker AXS Inc., Madison, Wisconsin, USA.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810048890/nk2075sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810048890/nk2075Isup2.hkl

checkCIF report


Comment top

In solutions, 4-quinazolinone could have in principle three isomers—1H, 3H, and 4-OH, as shown in Figure 1, with preference of 3H-tautomer. Recently, the crystal structure of a CdII coordination complex has been reported, in which 3H-quinazolin-4-one (3H-tautomer) acted as a ligand (Turgunov & Englert, 2010). We now report the structure of a CuII complex in which 1H-quinazolin-4-one (1H-tautomer) acts as a ligand.

In the title compound, CuII ion is located on the inversion center and has an octahedral coordination environment: two ligands coordinated via N atoms in position 3, two chloride ligands and two aqua ligands (Figure 2). The distances between Cu and coordination atoms are the following: d(Cu—N3) = 2.022 (2) Å, d(Cu—Cl) = 2.3232 (4) Å and d(Cu—Ow) = 2.512 (2) Å. Long distances of metal-aqua bonds than other four coordination bonds indicate existence of the Jahn-Teller elongation effect.

Aqua ligands are involved in intramolecular and intermolecular hydrogen bonding. Intramoleculer H-bonding is occurring with carbonyl group of the ligand. An intermolecular H-bonding of aqua and chloride ligands gives raise to chains along [001] (Figure 3). In addition, between ligand and water molecules are formed weak C–H···O hydrogen bonds. Intermolecular N—H···O and N—H···Cl hydrogen bonds formed between the organic and chloride ligands link molecular complexes into hydrogen-bonded chains along [100] (Figure 4; Table 1). Weak π···π ring interactions connect the molecular complexes along [010] and [001] directions. [Cg1···Cg1vi=3.678 (1) Å, where Cg1=C4A–C5–C6–C7–C8–C8A; vi = x, 3/2 - y, 1/2 + z].

Related literature top

The crystal structure of pyrimidin-4(3H)-one was reported by Vaillancourt et al. (1998). For a Cd(II) coordination polymer with quinazolin-4(3H)-one, see: Turgunov & Englert (2010). For computational studies of quinazolin-4-one derivatives, see: Bakalova et al. (2004).

Experimental top

A solution of 17.05 mg (0.1 mmol) of copper(II) chloride dihydrate in 2 ml of water was added to a solution of 29.23 mg (0.2 mmol) of 3H-quinazolin-4-one in 5 ml of ethanol. The solution allowed to stand at room temperature for one week, after which light-blue crystals were obtained.

Refinement top

C-bound H atoms were positioned geometrically and treated as riding on their C atoms, with C—H distances of 0.93 Å (aromatic) and were refined with Uiso(H)=1.2Ueq(C). N-bound H atoms and water H atoms involved in the intermolecular hydrogen bonding were found by difference Fourier synthesis and refined isotropically with a distance restrains of 0.87 (2) and 0.85 (2) Å, respectively [N—H =0.84 (2) Å, O1w—H1w=0.84 (2) Å, O1w—H2w=0.85 (2) Å].

Structure description top

In solutions, 4-quinazolinone could have in principle three isomers—1H, 3H, and 4-OH, as shown in Figure 1, with preference of 3H-tautomer. Recently, the crystal structure of a CdII coordination complex has been reported, in which 3H-quinazolin-4-one (3H-tautomer) acted as a ligand (Turgunov & Englert, 2010). We now report the structure of a CuII complex in which 1H-quinazolin-4-one (1H-tautomer) acts as a ligand.

In the title compound, CuII ion is located on the inversion center and has an octahedral coordination environment: two ligands coordinated via N atoms in position 3, two chloride ligands and two aqua ligands (Figure 2). The distances between Cu and coordination atoms are the following: d(Cu—N3) = 2.022 (2) Å, d(Cu—Cl) = 2.3232 (4) Å and d(Cu—Ow) = 2.512 (2) Å. Long distances of metal-aqua bonds than other four coordination bonds indicate existence of the Jahn-Teller elongation effect.

Aqua ligands are involved in intramolecular and intermolecular hydrogen bonding. Intramoleculer H-bonding is occurring with carbonyl group of the ligand. An intermolecular H-bonding of aqua and chloride ligands gives raise to chains along [001] (Figure 3). In addition, between ligand and water molecules are formed weak C–H···O hydrogen bonds. Intermolecular N—H···O and N—H···Cl hydrogen bonds formed between the organic and chloride ligands link molecular complexes into hydrogen-bonded chains along [100] (Figure 4; Table 1). Weak π···π ring interactions connect the molecular complexes along [010] and [001] directions. [Cg1···Cg1vi=3.678 (1) Å, where Cg1=C4A–C5–C6–C7–C8–C8A; vi = x, 3/2 - y, 1/2 + z].

The crystal structure of pyrimidin-4(3H)-one was reported by Vaillancourt et al. (1998). For a Cd(II) coordination polymer with quinazolin-4(3H)-one, see: Turgunov & Englert (2010). For computational studies of quinazolin-4-one derivatives, see: Bakalova et al. (2004).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis PRO (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Bruker, 1998); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The 3H, 1H and 4-OH tautomers of 4-quinazolinone.
[Figure 2] Fig. 2. The molecular structure of the title complex with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 3] Fig. 3. Crystal packing of the title compound viewed along the a axis, showing the formation of a hydrogen-bonded chain along [001]. Molecular complexes are furhter linked by π–π stacking interactions, formed between ligands, along [010] and [001] directions [Cg1···Cg1vi=3.678 (1) Å].
[Figure 4] Fig. 4. Part of the crystal structure of the title compound showing the formation of a hydrogen-bonded chain along [100].
Diaquadichloridobis[quinazolin-4(1H)-one-κN3]copper(II) top
Crystal data top
[CuCl2(C8H6N2O)2(H2O)2]F(000) = 470
Mr = 462.77Dx = 1.813 Mg m−3
Monoclinic, P21/cCu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ybcCell parameters from 4533 reflections
a = 6.7438 (3) Åθ = 4.8–75.3°
b = 18.5328 (8) ŵ = 5.03 mm−1
c = 6.7831 (3) ÅT = 293 K
β = 90.735 (3)°Prism, light-blue
V = 847.69 (6) Å30.55 × 0.35 × 0.20 mm
Z = 2
Data collection top
Oxford Diffraction Xcalibur Ruby
diffractometer		1725 independent reflections
Radiation source: Enhance (Cu) X-ray Source1639 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
Detector resolution: 10.2576 pixels mm-1θmax = 77.1°, θmin = 4.8°
ω scansh = −5→8
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2007)		k = −23→22
Tmin = 0.366, Tmax = 1.000l = −8→8
5548 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.089 w = 1/[σ2(Fo2) + (0.0535P)2 + 0.3464P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max < 0.001
1725 reflectionsΔρmax = 0.37 e Å−3
137 parametersΔρmin = −0.46 e Å−3
3 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0067 (7)
Crystal data top
[CuCl2(C8H6N2O)2(H2O)2]V = 847.69 (6) Å3
Mr = 462.77Z = 2
Monoclinic, P21/cCu Kα radiation
a = 6.7438 (3) ŵ = 5.03 mm−1
b = 18.5328 (8) ÅT = 293 K
c = 6.7831 (3) Å0.55 × 0.35 × 0.20 mm
β = 90.735 (3)°
Data collection top
Oxford Diffraction Xcalibur Ruby
diffractometer		1725 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2007)		1639 reflections with I > 2σ(I)
Tmin = 0.366, Tmax = 1.000Rint = 0.040
5548 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0323 restraints
wR(F2) = 0.089H atoms treated by a mixture of independent and constrained refinement
S = 1.10Δρmax = 0.37 e Å−3
1725 reflectionsΔρmin = −0.46 e Å−3
137 parameters
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
xyzUiso*/Ueq
Cu10.00000.50000.50000.02135 (17)
Cl10.20934 (7)0.45671 (2)0.74764 (6)0.02750 (17)
O1−0.12427 (19)0.66628 (7)0.5870 (2)0.0280 (3)
N10.4508 (2)0.65113 (9)0.4461 (2)0.0227 (3)
C20.3358 (3)0.59405 (10)0.4636 (3)0.0229 (4)
H2A0.39360.54900.44580.028*
N30.1427 (2)0.59595 (8)0.5049 (2)0.0209 (3)
C40.0522 (3)0.66252 (9)0.5382 (3)0.0198 (4)
C4A0.1738 (3)0.72721 (10)0.5123 (2)0.0196 (4)
C50.0922 (3)0.79617 (10)0.5345 (3)0.0239 (4)
H5A−0.03990.80140.56930.029*
C60.2088 (3)0.85635 (11)0.5046 (3)0.0288 (4)
H6A0.15400.90220.51670.035*
C70.4101 (3)0.84875 (11)0.4560 (3)0.0311 (4)
H7A0.48710.88970.43630.037*
C80.4945 (3)0.78128 (11)0.4373 (3)0.0276 (4)
H8A0.62780.77640.40640.033*
C8A0.3762 (3)0.72057 (10)0.4656 (2)0.0205 (4)
O1W0.2398 (3)0.46004 (9)0.2416 (2)0.0356 (4)
H1W0.218 (5)0.4172 (11)0.274 (5)0.057 (10)*
H10.570 (3)0.6432 (17)0.417 (5)0.054 (9)*
H2W0.219 (6)0.462 (2)0.118 (3)0.065 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cu10.0191 (2)0.0140 (2)0.0308 (3)−0.00062 (12)−0.00334 (16)0.00158 (13)
Cl10.0262 (3)0.0276 (3)0.0286 (3)0.00254 (16)−0.00262 (18)0.00244 (16)
O10.0175 (6)0.0225 (7)0.0441 (8)0.0005 (5)0.0050 (5)−0.0008 (6)
N10.0149 (7)0.0243 (8)0.0290 (8)0.0010 (6)0.0006 (6)0.0016 (6)
C20.0209 (8)0.0190 (8)0.0289 (9)0.0025 (7)−0.0013 (7)0.0001 (7)
N30.0189 (7)0.0161 (7)0.0278 (7)0.0015 (5)−0.0009 (6)0.0013 (6)
C40.0198 (8)0.0170 (8)0.0224 (8)−0.0001 (6)−0.0017 (6)−0.0003 (6)
C4A0.0196 (8)0.0200 (8)0.0191 (7)−0.0005 (6)−0.0020 (6)−0.0002 (6)
C50.0256 (9)0.0208 (9)0.0253 (9)0.0006 (7)−0.0017 (7)−0.0013 (7)
C60.0395 (11)0.0180 (9)0.0287 (9)−0.0010 (8)−0.0041 (8)−0.0005 (7)
C70.0387 (11)0.0230 (10)0.0315 (10)−0.0141 (8)−0.0021 (8)0.0013 (7)
C80.0242 (9)0.0306 (10)0.0280 (9)−0.0088 (8)−0.0003 (7)0.0016 (8)
C8A0.0205 (8)0.0218 (9)0.0192 (7)−0.0024 (7)−0.0027 (6)0.0006 (6)
O1W0.0416 (9)0.0273 (8)0.0380 (9)0.0003 (6)0.0032 (7)−0.0016 (6)
Geometric parameters (Å, º) top
Cu1—N32.0221 (15)C4A—C51.400 (3)
Cu1—N3i2.0221 (15)C4A—C8A1.410 (3)
Cu1—Cl12.3232 (4)C5—C61.381 (3)
Cu1—Cl1i2.3232 (4)C5—H5A0.9300
O1—C41.241 (2)C6—C71.409 (3)
N1—C21.318 (2)C6—H6A0.9300
N1—C8A1.389 (2)C7—C81.380 (3)
N1—H10.841 (18)C7—H7A0.9300
C2—N31.336 (2)C8—C8A1.394 (3)
C2—H2A0.9300C8—H8A0.9300
N3—C41.396 (2)O1W—H1W0.837 (18)
C4—C4A1.464 (2)O1W—H2W0.848 (19)
N3—Cu1—N3i180.0C5—C4A—C4120.84 (16)
N3—Cu1—Cl190.40 (4)C8A—C4A—C4120.04 (16)
N3i—Cu1—Cl189.60 (4)C6—C5—C4A119.75 (18)
N3—Cu1—Cl1i89.60 (4)C6—C5—H5A120.1
N3i—Cu1—Cl1i90.40 (4)C4A—C5—H5A120.1
Cl1—Cu1—Cl1i180.0C5—C6—C7120.38 (19)
C2—N1—C8A121.43 (15)C5—C6—H6A119.8
C2—N1—H1116 (2)C7—C6—H6A119.8
C8A—N1—H1122 (2)C8—C7—C6120.79 (17)
N1—C2—N3125.02 (16)C8—C7—H7A119.6
N1—C2—H2A117.5C6—C7—H7A119.6
N3—C2—H2A117.5C7—C8—C8A118.77 (18)
C2—N3—C4119.11 (15)C7—C8—H8A120.6
C2—N3—Cu1116.00 (12)C8A—C8—H8A120.6
C4—N3—Cu1124.80 (12)N1—C8A—C8121.77 (17)
O1—C4—N3121.02 (16)N1—C8A—C4A117.05 (15)
O1—C4—C4A121.77 (16)C8—C8A—C4A121.17 (17)
N3—C4—C4A117.21 (15)H1W—O1W—H2W106 (3)
C5—C4A—C8A119.11 (16)
Symmetry code: (i) −x, −y+1, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W···O1i0.84 (2)1.92 (3)2.732 (2)162 (3)
O1W—H2W···Cl1ii0.85 (2)2.51 (2)3.355 (2)171 (4)
N1—H1···O1iii0.84 (2)2.39 (3)3.022 (2)133 (3)
N1—H1···Cl1iv0.84 (2)2.63 (3)3.324 (2)140 (3)
C2—H2A···O1W0.932.382.972 (3)121
C7—H7A···O1Wv0.932.573.421 (3)152
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, y, z−1; (iii) x+1, y, z; (iv) −x+1, −y+1, −z+1; (v) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula[CuCl2(C8H6N2O)2(H2O)2]
Mr462.77
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)6.7438 (3), 18.5328 (8), 6.7831 (3)
β (°) 90.735 (3)
V (Å3)847.69 (6)
Z2
Radiation typeCu Kα
µ (mm−1)5.03
Crystal size (mm)0.55 × 0.35 × 0.20
Data collection
DiffractometerOxford Diffraction Xcalibur Ruby
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2007)
Tmin, Tmax0.366, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections		5548, 1725, 1639
Rint0.040
(sin θ/λ)max (Å−1)0.632
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.089, 1.10
No. of reflections1725
No. of parameters137
No. of restraints3
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.37, −0.46

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Bruker, 1998), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W···O1i0.84 (2)1.92 (3)2.732 (2)162 (3)
O1W—H2W···Cl1ii0.85 (2)2.51 (2)3.355 (2)171 (4)
N1—H1···O1iii0.84 (2)2.39 (3)3.022 (2)133 (3)
N1—H1···Cl1iv0.84 (2)2.63 (3)3.324 (2)140 (3)
C2—H2A···O1W0.93002.38002.972 (3)121.00
C7—H7A···O1Wv0.93002.57003.421 (3)152.00
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, y, z−1; (iii) x+1, y, z; (iv) −x+1, −y+1, −z+1; (v) −x+1, y+1/2, −z+1/2.
 

Acknowledgements

We thank the Academy of Sciences of the Republic of Uzbekistan for supporting this study (grant FA–F3–T045).

References

First citationBakalova, S. M., Santos, A. G., Timcheva, I., Kaneti, J., Filipova, I. L., Dobrikov, G. M. & Dimitrov, V. D. (2004). J. Mol. Struct. (THEOCHEM), 710, 229–234.  Web of Science CrossRef CAS Google Scholar
 First citationBruker (1998). XP. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationOxford Diffraction (2007). CrysAlis PRO. Oxford Diffraction Ltd, Abingdon, England.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationTurgunov, K. & Englert, U. (2010). Acta Cryst. E66, m1457.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationVaillancourt, L., Simard, M. & Wuest, J. D. (1998). J. Org. Chem. 63, 9746–9752.  Web of Science CSD CrossRef CAS Google Scholar
 First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
Volume 66| Part 12| December 2010| Page m1680
https://doi.org/10.1107/S1600536810048890
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