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Acta Crystallogr Sect E Struct Rep Online. 2010 September 1; 66(Pt 9): m1126.
Published online 2010 August 18. doi:  10.1107/S1600536810032381
PMCID: PMC3007975

Bis[(2-amino­phen­yl)methanol-κ2 N,O]bis­(nitrato-κO)cobalt(II)

Abstract

The asymmetric unit of the title compound, [Co(NO3)2(C7H9NO)2], contains one-half of the mol­ecule. The CoII atom (site symmetry 2) is six-coordinate in a distorted octahedral configuration bonded by two N and two O atoms from two (2-amino­phen­yl)methanol ligands and two O atoms from the two nitrate anions. Crystal packing is stabilized by inter­molecular N—H(...)O, O—H(...)O and C—H(...)O hydrogen-bonding inter­actions.

Related literature

For related structures with different metal atoms, see: Bandoli et al. (2002 [triangle]); Lewiriski et al. (1998 [triangle]); Esmhosseini (2010 [triangle]); Esmhosseini & Maleki (2010 [triangle]). For bond distances and angles, see: Allen (2002 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1126-scheme1.jpg

Experimental

Crystal data

  • [Co(NO3)2(C7H9NO)2]
  • M r = 429.25
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1126-efi1.jpg
  • a = 7.2554 (6) Å
  • b = 10.1685 (7) Å
  • c = 23.250 (2) Å
  • V = 1715.3 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.05 mm−1
  • T = 120 K
  • 0.50 × 0.20 × 0.15 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2003 [triangle]) T min = 0.768, T max = 0.861
  • 6514 measured reflections
  • 2271 independent reflections
  • 2065 reflections with I > 2σ(I)
  • R int = 0.046

Refinement

  • R[F 2 > 2σ(F 2)] = 0.032
  • wR(F 2) = 0.088
  • S = 1.08
  • 2271 reflections
  • 135 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.46 e Å−3
  • Δρmin = −0.46 e Å−3

Data collection: SMART (Bruker, 1998 [triangle]); cell refinement: SAINT (Bruker, 1998 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Selected geometric parameters (Å, °)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810032381/jj2052sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810032381/jj2052Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors are grateful to the University of Urmiyeh for financial support.

supplementary crystallographic information

Comment

Only four metal complexes with the (2-aminophenyl)methanol, bidentate ligand have been prepared and include the Re (Bandoli et al., 2002), Al (Lewiriski et al., 1998), Zn (Esmhosseini, 2010) and Mn (Esmhosseini & Maleki, 2010) compounds. We report herein the synthesis and crystal structure of the Co analogue compound, [Co(C7H9NO)2(NO3)2].

The asymmetric unit of the title compound, [Co(C7H9NO)2(NO3)2], contains one-half of the molecule (Fig. 1). The CoII atom in the cation is six-coordinate in a distorted hexagonal configuration bonded by two N and two O atoms from two (2-aminophenyl)methanol ligands and two O atoms from the two nitrate anions. Bond distances and angles are in normal ranges (Allen, 2002). Intermolecular N—H···O, O—H···O and C—H···O hydrogen bonding stabilize the crystal structure, (Table 2, Fig. 2).

Experimental

For the preparation of the title compound, a solution of (2-aminophenyl)methanol (0.25 g, 2.00 mmol) in methanol (10 ml) was added to a solution of Co(NO3)2.6H2O (0.29 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, light violet block crystals of the title compound were isolated (yield 0.32 g, 74.5%).

Refinement

The H atoms on the C and N atoms were positioned geometrically, and refined as riding atoms, with C–H = 0.93 Å (CH), C–H = 0.97 Å (CH2), N–H = 0.88, 0.84 Å (NH2) and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C), Uiso(H) = 1.9Ueq(N). The H on O1 was located by a Fourier map and refined isotropically.

Figures

Fig. 1.
The molecular structure of the title molecule, [Co(C7H9NO)2(NO3)2], with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
Unit-cell packing diagram for title molecule, [Co(C7H9NO)2(NO3)2]. Hydrogen bonds are shown as dashed lines.

Crystal data

[Co(NO3)2(C7H9NO)2]F(000) = 884
Mr = 429.25Dx = 1.662 Mg m3
Orthorhombic, PnabMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2bc 2nCell parameters from 1009 reflections
a = 7.2554 (6) Åθ = 2.2–29.2°
b = 10.1685 (7) ŵ = 1.05 mm1
c = 23.250 (2) ÅT = 120 K
V = 1715.3 (3) Å3Block, light violet
Z = 40.50 × 0.20 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer2271 independent reflections
Radiation source: fine-focus sealed tube2065 reflections with I > 2σ(I)
graphiteRint = 0.046
[var phi] and ω scansθmax = 29.2°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2003)h = −6→9
Tmin = 0.768, Tmax = 0.861k = −11→13
6514 measured reflectionsl = −26→31

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088H atoms treated by a mixture of independent and constrained refinement
S = 1.08w = 1/[σ2(Fo2) + (0.0456P)2 + 0.8425P] where P = (Fo2 + 2Fc2)/3
2271 reflections(Δ/σ)max = 0.007
135 parametersΔρmax = 0.46 e Å3
0 restraintsΔρmin = −0.46 e Å3

Special details

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)

xyzUiso*/Ueq
O3−0.06393 (16)0.10499 (10)0.53584 (5)0.0194 (2)
O4−0.24657 (15)0.23434 (12)0.58377 (5)0.0213 (2)
O10.18951 (16)0.45350 (10)0.44211 (4)0.0155 (2)
H1E0.142 (3)0.524 (2)0.4531 (9)0.029 (6)*
C20.2247 (2)0.32739 (15)0.35482 (6)0.0145 (3)
C40.4195 (2)0.26108 (18)0.27496 (6)0.0230 (3)
H40.47940.28160.24070.028*
N2−0.11401 (17)0.21530 (11)0.55146 (5)0.0135 (2)
C70.23941 (19)0.19961 (13)0.37774 (7)0.0143 (3)
O2−0.02236 (15)0.31708 (9)0.53328 (5)0.0151 (2)
Co10.25000.30062 (2)0.50000.01128 (10)
C60.3427 (2)0.10409 (15)0.34922 (6)0.0179 (3)
H60.35080.01950.36420.022*
C30.3146 (2)0.35577 (15)0.30337 (6)0.0188 (3)
H30.30440.43960.28770.023*
C50.4337 (2)0.13548 (16)0.29835 (7)0.0223 (3)
H50.50440.07210.27980.027*
N10.15712 (18)0.17223 (12)0.43271 (5)0.0140 (2)
H1C0.162 (3)0.088 (2)0.4413 (9)0.028 (5)*
H1D0.044 (4)0.189 (2)0.4333 (10)0.027 (6)*
C10.1144 (2)0.43142 (13)0.38520 (6)0.0158 (3)
H1A0.11810.51260.36330.019*
H1B−0.01310.40360.38820.019*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O30.0226 (5)0.0110 (4)0.0246 (5)−0.0008 (4)0.0041 (4)−0.0014 (4)
O40.0135 (5)0.0244 (6)0.0259 (6)0.0003 (4)0.0074 (4)0.0004 (5)
O10.0207 (5)0.0104 (4)0.0152 (5)0.0035 (4)0.0008 (4)−0.0007 (4)
C20.0126 (6)0.0153 (6)0.0155 (6)−0.0010 (5)−0.0010 (5)−0.0010 (5)
C40.0208 (7)0.0333 (8)0.0149 (6)−0.0045 (6)0.0041 (6)−0.0032 (6)
N20.0116 (5)0.0129 (5)0.0160 (5)−0.0006 (4)−0.0010 (4)0.0005 (4)
C70.0129 (7)0.0145 (6)0.0155 (6)−0.0022 (5)−0.0001 (5)−0.0014 (5)
O20.0134 (5)0.0101 (4)0.0219 (5)−0.0008 (3)0.0040 (4)0.0008 (4)
Co10.01166 (16)0.00913 (15)0.01306 (15)0.0000.00220 (9)0.000
C60.0174 (7)0.0175 (6)0.0190 (6)0.0009 (5)−0.0002 (5)−0.0043 (5)
C30.0195 (7)0.0214 (7)0.0156 (6)−0.0048 (6)−0.0004 (6)0.0016 (5)
C50.0195 (7)0.0267 (8)0.0206 (7)0.0012 (6)0.0027 (6)−0.0092 (6)
N10.0141 (6)0.0112 (5)0.0168 (5)−0.0004 (4)0.0021 (4)0.0007 (4)
C10.0151 (6)0.0148 (6)0.0175 (6)0.0015 (5)−0.0011 (5)0.0016 (5)

Geometric parameters (Å, °)

O3—N21.2338 (15)O2—Co12.1288 (11)
O4—N21.2356 (16)Co1—O1i2.1025 (10)
O1—C11.4485 (17)Co1—O2i2.1288 (11)
O1—Co12.1025 (10)Co1—N1i2.1463 (12)
O1—H1E0.83 (2)Co1—N12.1463 (12)
C2—C31.393 (2)C6—C51.392 (2)
C2—C71.408 (2)C6—H60.9300
C2—C11.503 (2)C3—H30.9300
C4—C51.392 (2)C5—H50.9300
C4—C31.394 (2)N1—H1C0.88 (2)
C4—H40.9300N1—H1D0.84 (3)
N2—O21.3008 (15)C1—H1A0.9700
C7—C61.394 (2)C1—H1B0.9700
C7—N11.4378 (19)
C1—O1—Co1123.28 (8)O1—Co1—N185.27 (4)
C1—O1—H1E104.9 (15)O1i—Co1—N1169.09 (5)
Co1—O1—H1E121.7 (14)O2—Co1—N191.22 (5)
C3—C2—C7118.74 (14)O2i—Co1—N194.26 (4)
C3—C2—C1120.48 (13)N1i—Co1—N1105.07 (7)
C7—C2—C1120.78 (13)C5—C6—C7119.95 (14)
C5—C4—C3119.28 (14)C5—C6—H6120.0
C5—C4—H4120.4C7—C6—H6120.0
C3—C4—H4120.4C2—C3—C4121.30 (15)
O3—N2—O4123.42 (12)C2—C3—H3119.3
O3—N2—O2118.50 (12)C4—C3—H3119.3
O4—N2—O2118.08 (12)C6—C5—C4120.50 (14)
C6—C7—C2120.22 (14)C6—C5—H5119.8
C6—C7—N1120.72 (13)C4—C5—H5119.8
C2—C7—N1118.92 (13)C7—N1—Co1113.56 (9)
N2—O2—Co1122.01 (8)C7—N1—H1C112.0 (14)
O1—Co1—O1i84.64 (6)Co1—N1—H1C114.4 (14)
O1—Co1—O288.90 (4)C7—N1—H1D112.5 (16)
O1i—Co1—O284.43 (4)Co1—N1—H1D100.0 (16)
O1—Co1—O2i84.43 (4)H1C—N1—H1D103 (2)
O1i—Co1—O2i88.90 (4)O1—C1—C2109.76 (11)
O2—Co1—O2i170.98 (5)O1—C1—H1A109.7
O1—Co1—N1i169.09 (5)C2—C1—H1A109.7
O1i—Co1—N1i85.27 (4)O1—C1—H1B109.7
O2—Co1—N1i94.26 (4)C2—C1—H1B109.7
O2i—Co1—N1i91.22 (5)H1A—C1—H1B108.2
C3—C2—C7—C60.2 (2)N1—C7—C6—C5−174.82 (14)
C1—C2—C7—C6−179.79 (13)C7—C2—C3—C4−0.8 (2)
C3—C2—C7—N1175.93 (13)C1—C2—C3—C4179.16 (14)
C1—C2—C7—N1−4.0 (2)C5—C4—C3—C20.4 (2)
O3—N2—O2—Co1−18.93 (17)C7—C6—C5—C4−1.3 (2)
O4—N2—O2—Co1160.75 (10)C3—C4—C5—C60.7 (2)
C1—O1—Co1—O1i−174.89 (13)C6—C7—N1—Co1120.28 (12)
C1—O1—Co1—O2−90.38 (11)C2—C7—N1—Co1−55.46 (15)
C1—O1—Co1—O2i95.70 (11)O1—Co1—N1—C749.56 (10)
C1—O1—Co1—N1i162.6 (2)O1i—Co1—N1—C772.1 (3)
C1—O1—Co1—N10.94 (11)O2—Co1—N1—C7138.36 (10)
N2—O2—Co1—O1145.62 (10)O2i—Co1—N1—C7−34.48 (10)
N2—O2—Co1—O1i−129.65 (10)N1i—Co1—N1—C7−126.90 (11)
N2—O2—Co1—N1i−44.83 (10)Co1—O1—C1—C2−49.00 (15)
N2—O2—Co1—N160.38 (10)C3—C2—C1—O1−119.95 (14)
C2—C7—C6—C50.9 (2)C7—C2—C1—O160.01 (17)

Symmetry codes: (i) −x+1/2, y, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1C···O3ii0.88 (2)2.15 (2)2.9897 (16)158 (2)
N1—H1D···O4iii0.84 (3)2.24 (3)3.0689 (17)169 (2)
O1—H1E···O2iv0.84 (2)1.86 (2)2.6908 (14)172 (2)
C1—H1B···O4iii0.972.543.4145 (18)151.

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JJ2052).

References

  • Allen, F. H. (2002). Acta Cryst. B58, 380–388. [PubMed]
  • Bandoli, G., Dolmella, A., Gerber, T. I. A., Mpinda, D., Perils, J. & Preez, J. G. H. (2002). J. Coord. Chem.55, 823–833.
  • Bruker (1998). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2003). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Esmhosseini, M. (2010). Acta Cryst. E66, m1057. [PMC free article] [PubMed]
  • Esmhosseini, M. & Maleki, S. (2010). Acta Cryst. E66, m1052. [PMC free article] [PubMed]
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  • Lewiriski, J., Zachara, J. & Kopec, T. (1998). Inorg. Chem. Commun.1, 182–184.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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