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

Esmhosseini, M.

doi:10.1107/S1600536810030485

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 9| September 2010| Page m1057

https://doi.org/10.1107/S1600536810030485

Open

access

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

Majid Esmhosseini ^a ^*

^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 Zn^II 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 ); Lewiński et al. (1998 ).

Experimental

Crystal data

[Zn(NO₃)₂(C₇H₉NO)₂]
M_r = 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 ) T_min = 0.857, T_max = 0.980
14935 measured reflections
3005 independent reflections
2063 reflections with I > 2σ(I)
R_int = 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
Δρ_max = 0.67 e Å⁻³
Δρ_min = −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	D⋯A	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 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810030485/hy2332sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810030485/hy2332Isup2.hkl

checkCIF report

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 Zn^II 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%).

Structure description top

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

	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.]
	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
M_r = 435.71	D_x = 1.653 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 1421 reflections
a = 23.386 (5) Å	θ = 2.2–32.0°
b = 10.193 (2) Å	µ = 1.46 mm⁻¹
c = 7.3442 (15) Å	T = 298 K
V = 1750.7 (6) Å³	Needle, colorless
Z = 4	0.35 × 0.03 × 0.02 mm

Data collection top

Bruker APEX CCD diffractometer	3005 independent reflections
Radiation source: fine-focus sealed tube	2063 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.140
φ and ω scans	θ_max = 32.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −34→34
T_min = 0.857, T_max = 0.980	k = −15→13
14935 measured reflections	l = −9→10

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.088	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.154	H atoms treated by a mixture of independent and constrained refinement
S = 1.26	w = 1/[σ²(F_o²) + (0.0303P)² + 3.223P] where P = (F_o² + 2F_c²)/3
3005 reflections	(Δ/σ)_max = 0.004
135 parameters	Δρ_max = 0.67 e Å⁻³
0 restraints	Δρ_min = −0.76 e Å⁻³

Crystal data top

[Zn(NO₃)₂(C₇H₉NO)₂]	V = 1750.7 (6) Å³
M_r = 435.71	Z = 4
Orthorhombic, Pbcn	Mo Kα radiation
a = 23.386 (5) Å	µ = 1.46 mm⁻¹
b = 10.193 (2) Å	T = 298 K
c = 7.3442 (15) Å	0.35 × 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)
T_min = 0.857, T_max = 0.980	R_int = 0.140
14935 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.088	0 restraints
wR(F²) = 0.154	H atoms treated by a mixture of independent and constrained refinement
S = 1.26	Δρ_max = 0.67 e Å⁻³
3005 reflections	Δρ_min = −0.76 e Å⁻³
135 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.3876 (2)	0.4320 (4)	0.3878 (6)	0.0324 (9)
H1A	0.3663	0.5136	0.3834	0.039*
H1B	0.3910	0.4056	0.5142	0.039*
C2	0.35648 (17)	0.3286 (4)	0.2831 (5)	0.0270 (8)
C3	0.3046 (2)	0.3574 (5)	0.1974 (7)	0.0408 (11)
H3	0.2892	0.4413	0.2074	0.049*
C4	0.2756 (2)	0.2623 (7)	0.0976 (8)	0.0519 (15)
H4	0.2411	0.2826	0.0417	0.062*
C5	0.2980 (2)	0.1394 (7)	0.0818 (8)	0.0499 (14)
H5	0.2790	0.0768	0.0124	0.060*
C6	0.3488 (2)	0.1067 (5)	0.1679 (6)	0.0381 (10)
H6	0.3633	0.0220	0.1589	0.046*
C7	0.37800 (17)	0.2015 (4)	0.2681 (5)	0.0279 (7)
N1	0.43276 (16)	0.1728 (4)	0.3456 (5)	0.0262 (7)
H1C	0.439 (2)	0.097 (6)	0.339 (8)	0.040 (15)*
H1D	0.433 (3)	0.192 (7)	0.460 (9)	0.06 (2)*
N2	0.44748 (15)	0.2148 (4)	−0.1135 (4)	0.0286 (7)
O1	0.44352 (14)	0.4515 (3)	0.3116 (5)	0.0305 (7)
H1E	0.457 (3)	0.510 (7)	0.344 (9)	0.054 (19)*
O2	0.46612 (15)	0.3154 (3)	−0.0261 (4)	0.0316 (7)
O3	0.46254 (17)	0.1044 (3)	−0.0629 (5)	0.0427 (8)
O4	0.41587 (17)	0.2329 (4)	−0.2447 (5)	0.0484 (9)
Zn1	0.5000	0.29214 (6)	0.2500	0.02484 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.038 (2)	0.030 (2)	0.029 (2)	0.0063 (18)	0.0021 (18)	−0.0027 (16)
C2	0.0273 (17)	0.0312 (19)	0.022 (2)	−0.0029 (15)	0.0007 (13)	0.0042 (13)
C3	0.031 (2)	0.047 (3)	0.045 (3)	0.003 (2)	0.0000 (18)	0.009 (2)
C4	0.030 (2)	0.074 (4)	0.052 (3)	−0.005 (2)	−0.012 (2)	0.006 (3)
C5	0.039 (3)	0.065 (4)	0.046 (3)	−0.021 (3)	−0.007 (2)	−0.005 (3)
C6	0.044 (3)	0.037 (2)	0.033 (2)	−0.010 (2)	−0.004 (2)	−0.001 (2)
C7	0.0324 (16)	0.0315 (17)	0.0199 (17)	−0.0051 (16)	−0.0010 (15)	0.0002 (17)
N1	0.0344 (18)	0.0186 (15)	0.0257 (17)	−0.0002 (14)	−0.0053 (14)	0.0003 (12)
N2	0.0364 (17)	0.0277 (16)	0.0218 (14)	−0.0003 (16)	−0.0019 (13)	−0.0022 (14)
O1	0.0335 (15)	0.0188 (13)	0.0391 (16)	−0.0032 (12)	−0.0028 (13)	−0.0081 (12)
O2	0.0494 (18)	0.0201 (14)	0.0253 (14)	−0.0007 (13)	−0.0107 (13)	0.0000 (11)
O3	0.061 (2)	0.0234 (15)	0.0440 (19)	0.0019 (15)	−0.0116 (17)	−0.0025 (14)
O4	0.062 (2)	0.053 (2)	0.0302 (15)	−0.0018 (17)	−0.0188 (18)	−0.0012 (19)
Zn1	0.0289 (3)	0.0202 (2)	0.0254 (3)	0.000	−0.0063 (3)	0.000

Geometric parameters (Å, º) top

C1—O1	1.436 (6)	C6—C7	1.394 (6)
C1—C2	1.494 (6)	C6—H6	0.9300
C1—H1A	0.9700	C7—N1	1.432 (5)
C1—H1B	0.9700	N1—H1C	0.79 (6)
C2—C7	1.394 (6)	N1—H1D	0.86 (7)
C2—C3	1.399 (6)	N2—O4	1.228 (5)
C3—C4	1.391 (8)	N2—O3	1.236 (5)
C3—H3	0.9300	N2—O2	1.286 (5)
C4—C5	1.363 (9)	Zn1—O1	2.142 (3)
C4—H4	0.9300	O1—H1E	0.72 (7)
C5—C6	1.386 (7)	Zn1—O2	2.190 (3)
C5—H5	0.9300	Zn1—N1	2.108 (4)

O1—C1—C2	109.9 (3)	Zn1—N1—H1C	114 (4)
O1—C1—H1A	109.7	C7—N1—H1D	111 (4)
C2—C1—H1A	109.7	Zn1—N1—H1D	100 (4)
O1—C1—H1B	109.7	H1C—N1—H1D	106 (6)
C2—C1—H1B	109.7	O4—N2—O3	123.0 (4)
H1A—C1—H1B	108.2	O4—N2—O2	118.4 (4)
C7—C2—C3	118.2 (4)	O3—N2—O2	118.6 (3)
C7—C2—C1	121.3 (4)	C1—O1—Zn1	122.6 (3)
C3—C2—C1	120.4 (4)	C1—O1—H1E	113 (5)
C4—C3—C2	120.8 (5)	Zn1—O1—H1E	115 (5)
C4—C3—H3	119.6	N2—O2—Zn1	119.9 (2)
C2—C3—H3	119.6	N1—Zn1—N1ⁱ	109.5 (2)
C5—C4—C3	120.0 (5)	N1—Zn1—O1	84.67 (14)
C5—C4—H4	120.0	N1ⁱ—Zn1—O1	165.41 (13)
C3—C4—H4	120.0	N1—Zn1—O1ⁱ	165.41 (13)
C4—C5—C6	120.7 (5)	N1ⁱ—Zn1—O1ⁱ	84.67 (14)
C4—C5—H5	119.6	O1—Zn1—O1ⁱ	81.37 (18)
C6—C5—H5	119.6	N1—Zn1—O2ⁱ	91.37 (13)
C5—C6—C7	119.6 (5)	N1ⁱ—Zn1—O2ⁱ	95.81 (13)
C5—C6—H6	120.2	O1—Zn1—O2ⁱ	86.87 (12)
C7—C6—H6	120.2	O1ⁱ—Zn1—O2ⁱ	83.69 (12)
C6—C7—C2	120.6 (4)	N1—Zn1—O2	95.81 (13)
C6—C7—N1	120.4 (4)	N1ⁱ—Zn1—O2	91.37 (13)
C2—C7—N1	118.8 (4)	O1—Zn1—O2	83.69 (12)
C7—N1—Zn1	114.6 (3)	O1ⁱ—Zn1—O2	86.88 (12)
C7—N1—H1C	110 (4)	O2ⁱ—Zn1—O2	167.55 (15)

O1—C1—C2—C7	59.5 (5)	O3—N2—O2—Zn1	−19.1 (5)
O1—C1—C2—C3	−120.7 (4)	C7—N1—Zn1—N1ⁱ	−126.8 (3)
C7—C2—C3—C4	−1.0 (7)	C7—N1—Zn1—O1	49.8 (3)
C1—C2—C3—C4	179.1 (5)	C7—N1—Zn1—O1ⁱ	66.7 (6)
C2—C3—C4—C5	−0.3 (8)	C7—N1—Zn1—O2ⁱ	136.5 (3)
C3—C4—C5—C6	1.6 (9)	C7—N1—Zn1—O2	−33.3 (3)
C4—C5—C6—C7	−1.6 (8)	C1—O1—Zn1—N1	0.8 (3)
C5—C6—C7—C2	0.3 (7)	C1—O1—Zn1—N1ⁱ	168.0 (5)
C5—C6—C7—N1	−174.9 (4)	C1—O1—Zn1—O1ⁱ	−175.0 (4)
C3—C2—C7—C6	1.0 (6)	C1—O1—Zn1—O2ⁱ	−90.9 (3)
C1—C2—C7—C6	−179.2 (4)	C1—O1—Zn1—O2	97.3 (3)
C3—C2—C7—N1	176.2 (4)	N2—O2—Zn1—N1	−46.2 (3)
C1—C2—C7—N1	−3.9 (6)	N2—O2—Zn1—N1ⁱ	63.6 (3)
C6—C7—N1—Zn1	118.9 (4)	N2—O2—Zn1—O1	−130.2 (3)
C2—C7—N1—Zn1	−56.4 (4)	N2—O2—Zn1—O1ⁱ	148.2 (3)
C2—C1—O1—Zn1	−48.3 (4)	N2—O2—Zn1—O2ⁱ	−171.1 (3)
O4—N2—O2—Zn1	161.5 (3)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1C···O3ⁱⁱ	0.79 (6)	2.24 (6)	2.987 (5)	157 (6)
N1—H1D···O4ⁱⁱⁱ	0.86 (7)	2.24 (7)	3.096 (5)	169 (7)
O1—H1E···O2^iv	0.72 (7)	2.03 (7)	2.710 (4)	159 (7)
C1—H1B···O4ⁱⁱⁱ	0.97	2.56	3.441 (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]
M_r	435.71
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	298
a, b, c (Å)	23.386 (5), 10.193 (2), 7.3442 (15)
V (Å³)	1750.7 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.46
Crystal size (mm)	0.35 × 0.03 × 0.02

Data collection
Diffractometer	Bruker APEX CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.857, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	14935, 3005, 2063
R_int	0.140
(sin θ/λ)_max (Å⁻¹)	0.745

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.088, 0.154, 1.26
No. of reflections	3005
No. of parameters	135
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	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—O1	2.142 (3)	Zn1—N1	2.108 (4)
Zn1—O2	2.190 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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+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

Bandoli, 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
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Lewiński, J., Zachara, J. & Kopeć, T. (1998). Inorg. Chem. Commun. 1, 182–l84. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar