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

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

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

(Received 28 April 2012; accepted 30 April 2012; online 5 May 2012)

In the title complex, [NiCl2(C8H6N2O)2(H2O)2], the NiII ion is located on an inversion center and is six-coordinated by two N atoms of 1H-quinazolin-4-one ligands, two chloride ions and two water mol­ecules. The water mol­ecules are involved in intra- and inter­molecular O—H⋯O and O—H⋯Cl hydrogen bonding. Inter­molecular N—H⋯O and N—H⋯Cl hydrogen bonds are formed between ligands. In addition, weak ππ inter­actions are observed between the benzene rings of the ligands [centroid–centroid distance = 3.580 (3) Å]. The inter­molecular hydrogen bonds and ππ inter­actions lead to the formation of a three-dimensional supra­molecular network.

Related literature

For a Cd(II) coordination polymer with quinazolin-4(3H)-one, see: Turgunov & Englert (2010[Turgunov, K. & Englert, U. (2010). Acta Cryst. E66, m1457.]) and for a Cu(II) coordination compound with quinazolin-4(1H)-one, see: Turgunov et al. (2010[Turgunov, K., Shomurotova, S., Mukhamedov, N. & Tashkhodjaev, B. (2010). Acta Cryst. E66, m1680.]).

[Scheme 1]

Experimental

Crystal data
  • [NiCl2(C8H6N2O)2(H2O)2]

  • Mr = 457.94

  • Monoclinic, P 21 /c

  • a = 6.7800 (5) Å

  • b = 18.741 (2) Å

  • c = 6.6106 (5) Å

  • β = 93.782 (8)°

  • V = 838.14 (13) Å3

  • Z = 2

  • Cu Kα radiation

  • μ = 4.92 mm−1

  • T = 295 K

  • 0.16 × 0.16 × 0.04 mm

Data collection
  • Oxford Diffraction Xcalibur Ruby diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.621, Tmax = 1.000

  • 3040 measured reflections

  • 1686 independent reflections

  • 1046 reflections with I > 2σ(I)

  • Rint = 0.047

Refinement
  • R[F2 > 2σ(F2)] = 0.052

  • wR(F2) = 0.139

  • S = 0.94

  • 1686 reflections

  • 132 parameters

  • 2 restraints

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

  • Δρmax = 0.75 e Å−3

  • Δρmin = −0.51 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1W—H1W⋯Cl1i 0.85 (4) 2.56 (3) 3.371 (4) 160 (6)
O1W—H2W⋯O1ii 0.85 (5) 1.87 (6) 2.641 (5) 150 (11)
N1—H1A⋯O1iii 0.86 2.44 3.116 (5) 136
N1—H1A⋯Cl1iv 0.86 2.59 3.256 (4) 135
C2—H2A⋯O1W 0.93 2.42 2.958 (6) 117
Symmetry codes: (i) x, y, z-1; (ii) -x+1, -y+1, -z; (iii) x-1, y, z; (iv) -x, -y+1, -z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, 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 in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

In the title compound NiII ion is located on the inversion center and has an octahedral coordination enviroment: two ligands coordinated via N atoms, two chloride ligands and two aqua ligands (Figure 1). The distances between Ni and coordination atoms are the following: d(Ni–N3)= 2.112 (4) Å, d(Ni–Cl)=2.445 (1) Å, d(Ni–Ow)=2.084 (3) Å. In the isostructural CuII complex Cu–Ow distance was longer (2.512 Å) because of the Jahn-Teller elongation effect (Turgunov et al., 2010).

The flat quinazolinone ligand is a little tilted in respect to metal–nitrogen vector and the dihedral angle between the least squares plane through the ligand and the metal–halide–water plane amounts to 84.33 (9)°.

Aqua ligands are involved in intramolecular and intermolecular hydrogen bonding. Intramolecular 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 2). 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 3; Table 1). Weak π-π ring interactions connect the molecular complexes along [010] and [001] directions. [Cg1···Cg1v]=3.580 Å, where Cg1=C4AC5C6C7C8C8A; v=x, 3/2 - y,1/2 + z].

Related literature top

For a Cd(II) coordination polymer with quinazolin-4(3H)-one, see: Turgunov & Englert (2010) and for a Cu(II) coordination compound with quinazolin-4(1H)-one, see: Turgunov et al. (2010)

Experimental top

A solution of 23.77 mg (0.1 mmol) of nickel(II) chloride hexahydrate in 1 ml of water was added to a solution of 29.23 mg (0.2 mmol) of 3H-quinazolin-4-one in 3 ml of ethanol. The solution allowed to stand at 50° C temperature for one week, after which colourless crystals were obtained.

Refinement top

Ligand H atoms were positioned geometrically and treated as riding on their C and N atoms, with C—H distances of 0.93 Å (aromatic), N—H distance of 0.86 Å and were refined with Uiso(H)=1.2Ueq(C),Uiso(H)=1.2Ueq(N). Coordinated water H atoms were found by difference Fourier synthesis and refined isotropically with distance restrains of 0.85 Å [O1w—H1w =0.85 (4) Å, O1w—H2w = 0.85 (5) Å].

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title complex with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Crystal packing of the title compound viewed along the a direction showing the formation a hydrogen-bonded chain along [001].
[Figure 3] Fig. 3. Part of the crystal structure of the title compound showing the formation a hydrogen-bonded chain along [100].
Diaquadichloridobis[quinazolin-4(1H)-one-κN3]nickel(II) top
Crystal data top
[NiCl2(C8H6N2O)2(H2O)2]F(000) = 468
Mr = 457.94Dx = 1.815 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybcCell parameters from 792 reflections
a = 6.7800 (5) Åθ = 4.7–75.6°
b = 18.741 (2) ŵ = 4.92 mm1
c = 6.6106 (5) ÅT = 295 K
β = 93.782 (8)°Rhombic plates, colourless
V = 838.14 (13) Å30.16 × 0.16 × 0.04 mm
Z = 2
Data collection top
Oxford Diffraction Xcalibur Ruby
diffractometer
1686 independent reflections
Radiation source: Enhance (Cu) X-ray Source1046 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
Detector resolution: 10.2576 pixels mm-1θmax = 75.9°, θmin = 4.7°
ω scansh = 87
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
k = 2313
Tmin = 0.621, Tmax = 1.000l = 88
3040 measured reflections
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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139H atoms treated by a mixture of independent and constrained refinement
S = 0.94 w = 1/[σ2(Fo2) + (0.0729P)2]
where P = (Fo2 + 2Fc2)/3
1686 reflections(Δ/σ)max < 0.001
132 parametersΔρmax = 0.75 e Å3
2 restraintsΔρmin = 0.51 e Å3
Crystal data top
[NiCl2(C8H6N2O)2(H2O)2]V = 838.14 (13) Å3
Mr = 457.94Z = 2
Monoclinic, P21/cCu Kα radiation
a = 6.7800 (5) ŵ = 4.92 mm1
b = 18.741 (2) ÅT = 295 K
c = 6.6106 (5) Å0.16 × 0.16 × 0.04 mm
β = 93.782 (8)°
Data collection top
Oxford Diffraction Xcalibur Ruby
diffractometer
1686 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
1046 reflections with I > 2σ(I)
Tmin = 0.621, Tmax = 1.000Rint = 0.047
3040 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0522 restraints
wR(F2) = 0.139H atoms treated by a mixture of independent and constrained refinement
S = 0.94Δρmax = 0.75 e Å3
1686 reflectionsΔρmin = 0.51 e Å3
132 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
Ni10.50000.50000.00000.0271 (3)
Cl10.30215 (17)0.45677 (7)0.27085 (17)0.0340 (3)
O10.6109 (5)0.66887 (19)0.0800 (5)0.0340 (8)
N10.0343 (5)0.6502 (2)0.0692 (6)0.0301 (9)
H1A0.09030.64340.09450.036*
C20.1533 (6)0.5947 (3)0.0494 (6)0.0285 (10)
H2A0.09710.54980.06840.034*
N30.3448 (5)0.5977 (2)0.0048 (5)0.0272 (9)
C40.4314 (7)0.6634 (3)0.0282 (7)0.0272 (10)
C4A0.3084 (7)0.7271 (3)0.0011 (7)0.0268 (10)
C50.3861 (7)0.7962 (3)0.0203 (7)0.0299 (10)
H5A0.52000.80250.05610.036*
C60.2672 (8)0.8542 (3)0.0110 (7)0.0348 (12)
H6A0.32050.89990.00040.042*
C70.0666 (8)0.8454 (3)0.0599 (7)0.0368 (12)
H7A0.01310.88550.07930.044*
C80.0178 (8)0.7785 (3)0.0805 (8)0.0357 (12)
H8A0.15250.77320.11340.043*
C8A0.1054 (7)0.7188 (3)0.0504 (7)0.0283 (10)
O1W0.2955 (5)0.4596 (2)0.2198 (5)0.0303 (7)
H1W0.328 (10)0.463 (4)0.342 (4)0.08 (2)*
H2W0.282 (18)0.4160 (17)0.189 (17)0.20 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0258 (5)0.0247 (6)0.0301 (6)0.0004 (5)0.0038 (4)0.0003 (5)
Cl10.0330 (6)0.0362 (7)0.0327 (6)0.0058 (5)0.0008 (4)0.0007 (5)
O10.0234 (15)0.029 (2)0.049 (2)0.0023 (15)0.0044 (14)0.0022 (17)
N10.0206 (17)0.035 (2)0.034 (2)0.0025 (17)0.0034 (15)0.0038 (19)
C20.029 (2)0.031 (3)0.026 (2)0.001 (2)0.0016 (18)0.002 (2)
N30.0273 (19)0.023 (2)0.031 (2)0.0022 (17)0.0002 (15)0.0001 (17)
C40.031 (2)0.025 (3)0.025 (2)0.001 (2)0.0043 (18)0.000 (2)
C4A0.028 (2)0.026 (3)0.026 (2)0.002 (2)0.0020 (18)0.002 (2)
C50.036 (2)0.026 (3)0.027 (2)0.001 (2)0.0003 (19)0.002 (2)
C60.048 (3)0.028 (3)0.029 (2)0.001 (2)0.000 (2)0.000 (2)
C70.050 (3)0.032 (3)0.029 (2)0.017 (3)0.002 (2)0.003 (2)
C80.032 (2)0.040 (3)0.034 (3)0.011 (2)0.002 (2)0.001 (2)
C8A0.029 (2)0.029 (3)0.027 (2)0.005 (2)0.0014 (18)0.002 (2)
O1W0.0299 (16)0.031 (2)0.0292 (17)0.0041 (16)0.0033 (13)0.0022 (17)
Geometric parameters (Å, º) top
Ni1—O1W2.084 (3)C4—C4A1.462 (7)
Ni1—O1Wi2.084 (3)C4A—C8A1.402 (6)
Ni1—N3i2.112 (4)C4A—C51.403 (7)
Ni1—N32.112 (4)C5—C61.362 (7)
Ni1—Cl12.4451 (12)C5—H5A0.9300
Ni1—Cl1i2.4451 (12)C6—C71.387 (7)
O1—C41.246 (5)C6—H6A0.9300
N1—C21.317 (6)C7—C81.381 (8)
N1—C8A1.375 (6)C7—H7A0.9300
N1—H1A0.8600C8—C8A1.402 (7)
C2—N31.314 (5)C8—H8A0.9300
C2—H2A0.9300O1W—H1W0.85 (4)
N3—C41.374 (6)O1W—H2W0.85 (5)
O1W—Ni1—O1Wi180.0 (2)O1—C4—N3121.1 (5)
O1W—Ni1—N3i90.21 (15)O1—C4—C4A120.5 (5)
O1Wi—Ni1—N3i89.79 (15)N3—C4—C4A118.4 (4)
O1W—Ni1—N389.79 (15)C8A—C4A—C5118.8 (5)
O1Wi—Ni1—N390.21 (15)C8A—C4A—C4119.0 (5)
N3i—Ni1—N3180.0 (2)C5—C4A—C4122.2 (4)
O1W—Ni1—Cl191.05 (11)C6—C5—C4A120.5 (5)
O1Wi—Ni1—Cl188.95 (11)C6—C5—H5A119.8
N3i—Ni1—Cl189.91 (11)C4A—C5—H5A119.8
N3—Ni1—Cl190.09 (11)C5—C6—C7120.1 (5)
O1W—Ni1—Cl1i88.95 (11)C5—C6—H6A119.9
O1Wi—Ni1—Cl1i91.05 (11)C7—C6—H6A119.9
N3i—Ni1—Cl1i90.09 (11)C8—C7—C6121.6 (5)
N3—Ni1—Cl1i89.91 (11)C8—C7—H7A119.2
Cl1—Ni1—Cl1i180.00 (6)C6—C7—H7A119.2
C2—N1—C8A121.4 (4)C7—C8—C8A118.1 (5)
C2—N1—H1A119.3C7—C8—H8A120.9
C8A—N1—H1A119.3C8A—C8—H8A120.9
N3—C2—N1125.3 (5)N1—C8A—C8122.1 (5)
N3—C2—H2A117.3N1—C8A—C4A117.2 (4)
N1—C2—H2A117.3C8—C8A—C4A120.8 (5)
C2—N3—C4118.7 (4)Ni1—O1W—H1W115 (5)
C2—N3—Ni1116.8 (3)Ni1—O1W—H2W105 (8)
C4—N3—Ni1124.5 (3)H1W—O1W—H2W110 (8)
Symmetry code: (i) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W···Cl1ii0.85 (4)2.56 (3)3.371 (4)160 (6)
O1W—H2W···O1i0.85 (5)1.87 (6)2.641 (5)150 (11)
N1—H1A···O1iii0.862.443.116 (5)136
N1—H1A···Cl1iv0.862.593.256 (4)135
C2—H2A···O1W0.932.422.958 (6)117
Symmetry codes: (i) x+1, y+1, z; (ii) x, y, z1; (iii) x1, y, z; (iv) x, y+1, z.

Experimental details

Crystal data
Chemical formula[NiCl2(C8H6N2O)2(H2O)2]
Mr457.94
Crystal system, space groupMonoclinic, P21/c
Temperature (K)295
a, b, c (Å)6.7800 (5), 18.741 (2), 6.6106 (5)
β (°) 93.782 (8)
V3)838.14 (13)
Z2
Radiation typeCu Kα
µ (mm1)4.92
Crystal size (mm)0.16 × 0.16 × 0.04
Data collection
DiffractometerOxford Diffraction Xcalibur Ruby
diffractometer
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
Tmin, Tmax0.621, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
3040, 1686, 1046
Rint0.047
(sin θ/λ)max1)0.629
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.052, 0.139, 0.94
No. of reflections1686
No. of parameters132
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.75, 0.51

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1W—H1W···Cl1i0.85 (4)2.56 (3)3.371 (4)160 (6)
O1W—H2W···O1ii0.85 (5)1.87 (6)2.641 (5)150 (11)
N1—H1A···O1iii0.862.443.116 (5)136
N1—H1A···Cl1iv0.862.593.256 (4)135
C2—H2A···O1W0.932.422.958 (6)117
Symmetry codes: (i) x, y, z1; (ii) x+1, y+1, z; (iii) x1, y, z; (iv) x, y+1, z.
 

Acknowledgements

We thank the Academy of Sciences of the Republic of Uzbekistan for supporting this study (grant FA–F7–T185).

References

First citationOxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, 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 citationTurgunov, K., Shomurotova, S., Mukhamedov, N. & Tashkhodjaev, B. (2010). Acta Cryst. E66, m1680.  Web of Science CSD CrossRef IUCr Journals 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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