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

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ISSN: 2056-9890

Bis[(2-amino­phen­yl)methanol-κ2N,O]bis­­(nitrato-κO)zinc(II)

aDepartment of Chemistry, University of Urmiyeh, Urmyieh, Iran
*Correspondence e-mail: m.esmhosseini@urmia.ac.ir

(Received 13 July 2010; accepted 30 July 2010; online 4 August 2010)

In the title compound, [Zn(NO3)2(C7H9NO)2], the ZnII atom, lying on a twofold rotation axis, is six-coordinated in a distorted octa­hedral geometry by two N atoms and two O atoms from two (2-amino­phen­yl)methanol ligands and two O atoms from two monodentate nitrate anions. Inter­molecular N—H⋯O, O—H⋯O and C—H⋯O hydrogen bonds stabilize the crystal structure.

Related literature

For related structures, see: Bandoli et al. (2002[Bandoli, G., Dolmella, A., Gerber, T. I. A., Mpinda, D., Perils, J. & Preez, J. G. H. (2002). J. Coord. Chem. 55, 823-833.]); Lewiński et al. (1998[Lewiński, J., Zachara, J. & Kopeć, T. (1998). Inorg. Chem. Commun. 1, 182-l84.]).

[Scheme 1]

Experimental

Crystal data
  • [Zn(NO3)2(C7H9NO)2]

  • Mr = 435.71

  • Orthorhombic, P b c n

  • a = 23.386 (5) Å

  • b = 10.193 (2) Å

  • c = 7.3442 (15) Å

  • V = 1750.7 (6) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.46 mm−1

  • T = 298 K

  • 0.35 × 0.03 × 0.02 mm

Data collection
  • Bruker APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.857, Tmax = 0.980

  • 14935 measured reflections

  • 3005 independent reflections

  • 2063 reflections with I > 2σ(I)

  • Rint = 0.140

Refinement
  • R[F2 > 2σ(F2)] = 0.088

  • wR(F2) = 0.154

  • S = 1.26

  • 3005 reflections

  • 135 parameters

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

  • Δρmax = 0.67 e Å−3

  • Δρmin = −0.76 e Å−3

Table 1
Selected bond lengths (Å)

Zn1—O1 2.142 (3)
Zn1—O2 2.190 (3)
Zn1—N1 2.108 (4)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1C⋯O3i 0.79 (6) 2.24 (6) 2.987 (5) 157 (6)
N1—H1D⋯O4ii 0.86 (7) 2.24 (7) 3.096 (5) 169 (7)
O1—H1E⋯O2iii 0.72 (7) 2.03 (7) 2.710 (4) 159 (7)
C1—H1B⋯O4ii 0.97 2.56 3.441 (6) 150
Symmetry codes: (i) [x, -y, z+{\script{1\over 2}}]; (ii) x, y, z+1; (iii) [x, -y+1, z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information


Comment top

(2-Aminophenyl)methanol is a bidentate ligand. There is only two complexes with this ligand reported, such as those of Re (Bandoli et al., 2002) and Al (Lewiński et al. 1998). We report herein the synthesis and structure of the title compound.

The asymmetric unit of the title compound (Fig. 1) contains half molecule. The ZnII atom, lying on a twofold rotation axis, is six-coordinated in a distorted octahedral geometry by two N atoms and two O atoms from two (2-aminophenyl)methanol ligands and two O atoms from two nitrate anions (Table 1). Intermolecular N—H···O, O—H···O and C—H···O hydrogen bonds stabilize the crystal structure (Fig. 2, Table 2).

Related literature top

For related structures, see: Bandoli et al. (2002); Lewiński et al. (1998).

Experimental top

A solution of (2-aminophenyl)methanol (0.25 g, 2.00 mmol) in methanol (10 ml) was added to a solution of Zn(NO3)2.4H2O (0.26 g, 1.00 mmol) in methanol (10 ml) and the resulting colorless solution was stirred for 20 min at 313 K. This solution was left to evaporate slowly at room temperature. After one week, colorless needle crystals of the title compound were isolated (yield: 0.32 g, 73.4%).

Refinement top

C-bound H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 (aromatic) and 0.97 (CH2) Å and Uiso(H) = 1.2Ueq(C). H atoms of the amino and hydroxy groups were located in a difference Fourier map and refined isotropically.

Structure description top

(2-Aminophenyl)methanol is a bidentate ligand. There is only two complexes with this ligand reported, such as those of Re (Bandoli et al., 2002) and Al (Lewiński et al. 1998). We report herein the synthesis and structure of the title compound.

The asymmetric unit of the title compound (Fig. 1) contains half molecule. The ZnII atom, lying on a twofold rotation axis, is six-coordinated in a distorted octahedral geometry by two N atoms and two O atoms from two (2-aminophenyl)methanol ligands and two O atoms from two nitrate anions (Table 1). Intermolecular N—H···O, O—H···O and C—H···O hydrogen bonds stabilize the crystal structure (Fig. 2, Table 2).

For related structures, see: Bandoli et al. (2002); Lewiński et al. (1998).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry code: (a) 1 - x, y, 1/2 - z.]
[Figure 2] Fig. 2. Crystal packing diagram for the title compound. Dashed lines denote hydrogen bonds.
Bis[(2-aminophenyl)methanol-κ2N,O]bis(nitrato- κO)zinc(II) top
Crystal data top
[Zn(NO3)2(C7H9NO)2]F(000) = 896
Mr = 435.71Dx = 1.653 Mg m3
Orthorhombic, PbcnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2abCell parameters from 1421 reflections
a = 23.386 (5) Åθ = 2.2–32.0°
b = 10.193 (2) ŵ = 1.46 mm1
c = 7.3442 (15) ÅT = 298 K
V = 1750.7 (6) Å3Needle, colorless
Z = 40.35 × 0.03 × 0.02 mm
Data collection top
Bruker APEX CCD
diffractometer
3005 independent reflections
Radiation source: fine-focus sealed tube2063 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.140
φ and ω scansθmax = 32.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 3434
Tmin = 0.857, Tmax = 0.980k = 1513
14935 measured reflectionsl = 910
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)] = 0.088Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154H atoms treated by a mixture of independent and constrained refinement
S = 1.26 w = 1/[σ2(Fo2) + (0.0303P)2 + 3.223P]
where P = (Fo2 + 2Fc2)/3
3005 reflections(Δ/σ)max = 0.004
135 parametersΔρmax = 0.67 e Å3
0 restraintsΔρmin = 0.76 e Å3
Crystal data top
[Zn(NO3)2(C7H9NO)2]V = 1750.7 (6) Å3
Mr = 435.71Z = 4
Orthorhombic, PbcnMo Kα radiation
a = 23.386 (5) ŵ = 1.46 mm1
b = 10.193 (2) ÅT = 298 K
c = 7.3442 (15) Å0.35 × 0.03 × 0.02 mm
Data collection top
Bruker APEX CCD
diffractometer
3005 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2063 reflections with I > 2σ(I)
Tmin = 0.857, Tmax = 0.980Rint = 0.140
14935 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0880 restraints
wR(F2) = 0.154H atoms treated by a mixture of independent and constrained refinement
S = 1.26Δρmax = 0.67 e Å3
3005 reflectionsΔρmin = 0.76 e Å3
135 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.3876 (2)0.4320 (4)0.3878 (6)0.0324 (9)
H1A0.36630.51360.38340.039*
H1B0.39100.40560.51420.039*
C20.35648 (17)0.3286 (4)0.2831 (5)0.0270 (8)
C30.3046 (2)0.3574 (5)0.1974 (7)0.0408 (11)
H30.28920.44130.20740.049*
C40.2756 (2)0.2623 (7)0.0976 (8)0.0519 (15)
H40.24110.28260.04170.062*
C50.2980 (2)0.1394 (7)0.0818 (8)0.0499 (14)
H50.27900.07680.01240.060*
C60.3488 (2)0.1067 (5)0.1679 (6)0.0381 (10)
H60.36330.02200.15890.046*
C70.37800 (17)0.2015 (4)0.2681 (5)0.0279 (7)
N10.43276 (16)0.1728 (4)0.3456 (5)0.0262 (7)
H1C0.439 (2)0.097 (6)0.339 (8)0.040 (15)*
H1D0.433 (3)0.192 (7)0.460 (9)0.06 (2)*
N20.44748 (15)0.2148 (4)0.1135 (4)0.0286 (7)
O10.44352 (14)0.4515 (3)0.3116 (5)0.0305 (7)
H1E0.457 (3)0.510 (7)0.344 (9)0.054 (19)*
O20.46612 (15)0.3154 (3)0.0261 (4)0.0316 (7)
O30.46254 (17)0.1044 (3)0.0629 (5)0.0427 (8)
O40.41587 (17)0.2329 (4)0.2447 (5)0.0484 (9)
Zn10.50000.29214 (6)0.25000.02484 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.038 (2)0.030 (2)0.029 (2)0.0063 (18)0.0021 (18)0.0027 (16)
C20.0273 (17)0.0312 (19)0.022 (2)0.0029 (15)0.0007 (13)0.0042 (13)
C30.031 (2)0.047 (3)0.045 (3)0.003 (2)0.0000 (18)0.009 (2)
C40.030 (2)0.074 (4)0.052 (3)0.005 (2)0.012 (2)0.006 (3)
C50.039 (3)0.065 (4)0.046 (3)0.021 (3)0.007 (2)0.005 (3)
C60.044 (3)0.037 (2)0.033 (2)0.010 (2)0.004 (2)0.001 (2)
C70.0324 (16)0.0315 (17)0.0199 (17)0.0051 (16)0.0010 (15)0.0002 (17)
N10.0344 (18)0.0186 (15)0.0257 (17)0.0002 (14)0.0053 (14)0.0003 (12)
N20.0364 (17)0.0277 (16)0.0218 (14)0.0003 (16)0.0019 (13)0.0022 (14)
O10.0335 (15)0.0188 (13)0.0391 (16)0.0032 (12)0.0028 (13)0.0081 (12)
O20.0494 (18)0.0201 (14)0.0253 (14)0.0007 (13)0.0107 (13)0.0000 (11)
O30.061 (2)0.0234 (15)0.0440 (19)0.0019 (15)0.0116 (17)0.0025 (14)
O40.062 (2)0.053 (2)0.0302 (15)0.0018 (17)0.0188 (18)0.0012 (19)
Zn10.0289 (3)0.0202 (2)0.0254 (3)0.0000.0063 (3)0.000
Geometric parameters (Å, º) top
C1—O11.436 (6)C6—C71.394 (6)
C1—C21.494 (6)C6—H60.9300
C1—H1A0.9700C7—N11.432 (5)
C1—H1B0.9700N1—H1C0.79 (6)
C2—C71.394 (6)N1—H1D0.86 (7)
C2—C31.399 (6)N2—O41.228 (5)
C3—C41.391 (8)N2—O31.236 (5)
C3—H30.9300N2—O21.286 (5)
C4—C51.363 (9)Zn1—O12.142 (3)
C4—H40.9300O1—H1E0.72 (7)
C5—C61.386 (7)Zn1—O22.190 (3)
C5—H50.9300Zn1—N12.108 (4)
O1—C1—C2109.9 (3)Zn1—N1—H1C114 (4)
O1—C1—H1A109.7C7—N1—H1D111 (4)
C2—C1—H1A109.7Zn1—N1—H1D100 (4)
O1—C1—H1B109.7H1C—N1—H1D106 (6)
C2—C1—H1B109.7O4—N2—O3123.0 (4)
H1A—C1—H1B108.2O4—N2—O2118.4 (4)
C7—C2—C3118.2 (4)O3—N2—O2118.6 (3)
C7—C2—C1121.3 (4)C1—O1—Zn1122.6 (3)
C3—C2—C1120.4 (4)C1—O1—H1E113 (5)
C4—C3—C2120.8 (5)Zn1—O1—H1E115 (5)
C4—C3—H3119.6N2—O2—Zn1119.9 (2)
C2—C3—H3119.6N1—Zn1—N1i109.5 (2)
C5—C4—C3120.0 (5)N1—Zn1—O184.67 (14)
C5—C4—H4120.0N1i—Zn1—O1165.41 (13)
C3—C4—H4120.0N1—Zn1—O1i165.41 (13)
C4—C5—C6120.7 (5)N1i—Zn1—O1i84.67 (14)
C4—C5—H5119.6O1—Zn1—O1i81.37 (18)
C6—C5—H5119.6N1—Zn1—O2i91.37 (13)
C5—C6—C7119.6 (5)N1i—Zn1—O2i95.81 (13)
C5—C6—H6120.2O1—Zn1—O2i86.87 (12)
C7—C6—H6120.2O1i—Zn1—O2i83.69 (12)
C6—C7—C2120.6 (4)N1—Zn1—O295.81 (13)
C6—C7—N1120.4 (4)N1i—Zn1—O291.37 (13)
C2—C7—N1118.8 (4)O1—Zn1—O283.69 (12)
C7—N1—Zn1114.6 (3)O1i—Zn1—O286.88 (12)
C7—N1—H1C110 (4)O2i—Zn1—O2167.55 (15)
O1—C1—C2—C759.5 (5)O3—N2—O2—Zn119.1 (5)
O1—C1—C2—C3120.7 (4)C7—N1—Zn1—N1i126.8 (3)
C7—C2—C3—C41.0 (7)C7—N1—Zn1—O149.8 (3)
C1—C2—C3—C4179.1 (5)C7—N1—Zn1—O1i66.7 (6)
C2—C3—C4—C50.3 (8)C7—N1—Zn1—O2i136.5 (3)
C3—C4—C5—C61.6 (9)C7—N1—Zn1—O233.3 (3)
C4—C5—C6—C71.6 (8)C1—O1—Zn1—N10.8 (3)
C5—C6—C7—C20.3 (7)C1—O1—Zn1—N1i168.0 (5)
C5—C6—C7—N1174.9 (4)C1—O1—Zn1—O1i175.0 (4)
C3—C2—C7—C61.0 (6)C1—O1—Zn1—O2i90.9 (3)
C1—C2—C7—C6179.2 (4)C1—O1—Zn1—O297.3 (3)
C3—C2—C7—N1176.2 (4)N2—O2—Zn1—N146.2 (3)
C1—C2—C7—N13.9 (6)N2—O2—Zn1—N1i63.6 (3)
C6—C7—N1—Zn1118.9 (4)N2—O2—Zn1—O1130.2 (3)
C2—C7—N1—Zn156.4 (4)N2—O2—Zn1—O1i148.2 (3)
C2—C1—O1—Zn148.3 (4)N2—O2—Zn1—O2i171.1 (3)
O4—N2—O2—Zn1161.5 (3)
Symmetry code: (i) x+1, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1C···O3ii0.79 (6)2.24 (6)2.987 (5)157 (6)
N1—H1D···O4iii0.86 (7)2.24 (7)3.096 (5)169 (7)
O1—H1E···O2iv0.72 (7)2.03 (7)2.710 (4)159 (7)
C1—H1B···O4iii0.972.563.441 (6)150
Symmetry codes: (ii) x, y, z+1/2; (iii) x, y, z+1; (iv) x, y+1, z+1/2.

Experimental details

Crystal data
Chemical formula[Zn(NO3)2(C7H9NO)2]
Mr435.71
Crystal system, space groupOrthorhombic, Pbcn
Temperature (K)298
a, b, c (Å)23.386 (5), 10.193 (2), 7.3442 (15)
V3)1750.7 (6)
Z4
Radiation typeMo Kα
µ (mm1)1.46
Crystal size (mm)0.35 × 0.03 × 0.02
Data collection
DiffractometerBruker APEX CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.857, 0.980
No. of measured, independent and
observed [I > 2σ(I)] reflections
14935, 3005, 2063
Rint0.140
(sin θ/λ)max1)0.745
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.088, 0.154, 1.26
No. of reflections3005
No. of parameters135
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.67, 0.76

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top
Zn1—O12.142 (3)Zn1—N12.108 (4)
Zn1—O22.190 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1C···O3i0.79 (6)2.24 (6)2.987 (5)157 (6)
N1—H1D···O4ii0.86 (7)2.24 (7)3.096 (5)169 (7)
O1—H1E···O2iii0.72 (7)2.03 (7)2.710 (4)159 (7)
C1—H1B···O4ii0.972.563.441 (6)150
Symmetry codes: (i) x, y, z+1/2; (ii) x, y, z+1; (iii) x, y+1, z+1/2.
 

Acknowledgements

The author is grateful to the University of Urmiyeh for financial support.

References

First citationBandoli, G., Dolmella, A., Gerber, T. I. A., Mpinda, D., Perils, J. & Preez, J. G. H. (2002). J. Coord. Chem. 55, 823–833.  Web of Science CSD CrossRef CAS Google Scholar
First citationBruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
First citationLewiński, J., Zachara, J. & Kopeć, T. (1998). Inorg. Chem. Commun. 1, 182–l84.  Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
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