Bis{2-[bis­(2-hy­droxy­eth­yl)amino]­acetato-κ3O,N,O′}zinc(II)

Lo, K.M.; Ng, S.W.

doi:10.1107/S1600536810043217

metal-organic compounds

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Volume 66| Part 11| November 2010| Page m1485

https://doi.org/10.1107/S1600536810043217

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Bis{2-[bis(2-hydroxyethyl)amino]acetato-κ³O,N,O′}zinc(II)

Kong Mun Lo ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 22 October 2010; accepted 23 October 2010; online 30 October 2010)

In the crystal structure of the zinc(II) complex of bicine, [Zn(C₆H₁₂NO₄)₂], the deprotonated amino acid O,N,O′-chelates to the metal atom through a carboxylate O atom, a hydroxy O atom and the N atom, the three atoms occupying fac positions of the distorted octahedron surrounding the metal atom. The metal atom lies on a center of inversion. The uncoordinated carboxylate O atom is hydrogen bonded to the hydroxy groups of adjacent molecules, these two hydrogen bonds leading to the formation of a three-dimensional network.

Related literature

For the isostructural cobalt(II) analog, see: Zhao & Liu (2010 ).

Experimental

Crystal data

[Zn(C₆H₁₂NO₄)₂]
M_r = 389.70
Monoclinic, P 2₁ /c
a = 9.7863 (7) Å
b = 11.3715 (8) Å
c = 7.3462 (5) Å
β = 109.1495 (8)°
V = 772.28 (9) Å³
Z = 2
Mo Kα radiation
μ = 1.64 mm⁻¹
T = 100 K
0.25 × 0.20 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.685, T_max = 0.792
7174 measured reflections
1773 independent reflections
1634 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.021
wR(F²) = 0.062
S = 1.12
1773 reflections
114 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2ⁱ	0.84 (1)	1.85 (1)	2.651 (2)	161 (2)
O4—H4⋯O2ⁱⁱ	0.83 (1)	1.89 (1)	2.715 (2)	178 (3)
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810043217/xu5062sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810043217/xu5062Isup2.hkl

checkCIF report

Comment top

In the crystal structure of the cobalt(II) derivative of bicine, the deprotonated aminoacid N,O,O'-chelates to the metal atom through the nitrogen, carboxyl oxygen and hydroxyl oxygen atoms, the three atoms occupying fac positions of the octahedron (Zhao & Liu, 2010). The present zinc analog (Scheme I, Fig. 1) is isostructural. The double-bond carboxyl oxygen atom is hydrogen-bond acceptor to the coordinated as well as the free hydroxyl unit of adjacent molecules, these two hydrogen bonds leading to the formation of a three-dimensional network (Table 1).

Related literature top

For the isostructural cobalt(II) analog, see: Zhao & Liu (2010).

Experimental top

N,N-Bis(2-hydroxyethyl)glycine (0.94 g, 5.7 mmol) and zinc carbonate (0.36 g, 2.8 mmol) were heated in a 1:1 water:DMSO mixture (100 ml) for 1 h. The solution was filtered; colorless crystals were obtained upon slow evaporation of the filtrate.

Structure description top

For the isostructural cobalt(II) analog, see: Zhao & Liu (2010).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of Zn(C₆H₁₂NO₄)₂ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Bis{2-[bis(2-hydroxyethyl)amino]acetato- κ³O,N,O'}zinc(II) top

Crystal data top

[Zn(C₆H₁₂NO₄)₂]	F(000) = 408
M_r = 389.70	D_x = 1.676 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4608 reflections
a = 9.7863 (7) Å	θ = 2.2–28.3°
b = 11.3715 (8) Å	µ = 1.64 mm⁻¹
c = 7.3462 (5) Å	T = 100 K
β = 109.1495 (8)°	Block, colorless
V = 772.28 (9) Å³	0.25 × 0.20 × 0.15 mm
Z = 2

Data collection top

Bruker SMART APEX diffractometer	1773 independent reflections
Radiation source: fine-focus sealed tube	1634 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω scans	θ_max = 27.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.685, T_max = 0.792	k = −14→14
7174 measured reflections	l = −9→9

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)] = 0.021	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.062	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ²(F_o²) + (0.0283P)² + 0.4612P] where P = (F_o² + 2F_c²)/3
1773 reflections	(Δ/σ)_max = 0.001
114 parameters	Δρ_max = 0.43 e Å⁻³
2 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

[Zn(C₆H₁₂NO₄)₂]	V = 772.28 (9) Å³
M_r = 389.70	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.7863 (7) Å	µ = 1.64 mm⁻¹
b = 11.3715 (8) Å	T = 100 K
c = 7.3462 (5) Å	0.25 × 0.20 × 0.15 mm
β = 109.1495 (8)°

Data collection top

Bruker SMART APEX diffractometer	1773 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1634 reflections with I > 2σ(I)
T_min = 0.685, T_max = 0.792	R_int = 0.026
7174 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.021	2 restraints
wR(F²) = 0.062	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	Δρ_max = 0.43 e Å⁻³
1773 reflections	Δρ_min = −0.35 e Å⁻³
114 parameters

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

	x	y	z	U_iso*/U_eq
Zn1	0.5000	0.5000	0.5000	0.00889 (9)
O1	0.45689 (11)	0.33271 (9)	0.56937 (15)	0.0132 (2)
O2	0.28013 (11)	0.21247 (9)	0.57458 (17)	0.0167 (2)
O3	0.51490 (11)	0.55292 (9)	0.78390 (15)	0.0129 (2)
H3	0.564 (2)	0.6126 (14)	0.831 (3)	0.030 (6)*
O4	0.00548 (11)	0.66106 (11)	0.01696 (15)	0.0160 (2)
H4	−0.0808 (12)	0.678 (2)	−0.009 (3)	0.040 (7)*
N1	0.27253 (13)	0.52389 (11)	0.44766 (18)	0.0095 (2)
C1	0.32624 (16)	0.31061 (13)	0.5430 (2)	0.0116 (3)
C2	0.21180 (15)	0.40649 (12)	0.4649 (2)	0.0114 (3)
H2A	0.1466	0.3821	0.3363	0.014*
H2B	0.1528	0.4130	0.5511	0.014*
C3	0.26823 (16)	0.60594 (13)	0.6035 (2)	0.0128 (3)
H3A	0.1690	0.6082	0.6106	0.015*
H3B	0.2935	0.6862	0.5732	0.015*
C4	0.37309 (16)	0.56760 (14)	0.7966 (2)	0.0141 (3)
H4A	0.3757	0.6275	0.8955	0.017*
H4B	0.3400	0.4925	0.8360	0.017*
C5	0.20539 (15)	0.57679 (13)	0.2541 (2)	0.0114 (3)
H5A	0.2129	0.5197	0.1561	0.014*
H5B	0.2620	0.6472	0.2442	0.014*
C6	0.04786 (16)	0.61242 (13)	0.2055 (2)	0.0131 (3)
H6A	−0.0125	0.5431	0.2091	0.016*
H6B	0.0370	0.6713	0.2990	0.016*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.00708 (13)	0.00885 (13)	0.01018 (13)	−0.00067 (8)	0.00204 (9)	0.00051 (8)
O1	0.0092 (5)	0.0119 (5)	0.0173 (5)	−0.0003 (4)	0.0026 (4)	0.0023 (4)
O2	0.0106 (5)	0.0123 (5)	0.0236 (6)	−0.0021 (4)	0.0008 (4)	0.0057 (4)
O3	0.0102 (5)	0.0136 (5)	0.0133 (5)	−0.0013 (4)	0.0019 (4)	−0.0020 (4)
O4	0.0111 (5)	0.0223 (6)	0.0127 (5)	0.0045 (4)	0.0014 (4)	0.0056 (4)
N1	0.0094 (6)	0.0089 (5)	0.0098 (6)	−0.0002 (4)	0.0026 (5)	0.0004 (4)
C1	0.0120 (7)	0.0118 (6)	0.0100 (6)	0.0003 (5)	0.0021 (5)	0.0005 (5)
C2	0.0091 (7)	0.0114 (6)	0.0131 (7)	−0.0011 (5)	0.0029 (5)	0.0013 (5)
C3	0.0125 (7)	0.0127 (6)	0.0129 (7)	0.0015 (5)	0.0037 (6)	−0.0013 (5)
C4	0.0124 (7)	0.0184 (7)	0.0117 (7)	0.0001 (5)	0.0042 (6)	−0.0013 (6)
C5	0.0092 (7)	0.0133 (7)	0.0109 (7)	0.0007 (5)	0.0021 (5)	0.0016 (5)
C6	0.0106 (7)	0.0151 (7)	0.0118 (7)	0.0022 (5)	0.0012 (5)	0.0016 (5)

Geometric parameters (Å, º) top

Zn1—O1	2.0488 (10)	N1—C3	1.4882 (18)
Zn1—O1ⁱ	2.0488 (10)	C1—C2	1.533 (2)
Zn1—O3ⁱ	2.1292 (11)	C2—H2A	0.9900
Zn1—O3	2.1292 (11)	C2—H2B	0.9900
Zn1—N1ⁱ	2.1484 (13)	C3—C4	1.516 (2)
Zn1—N1	2.1484 (13)	C3—H3A	0.9900
O1—C1	1.2542 (18)	C3—H3B	0.9900
O2—C1	1.2537 (18)	C4—H4A	0.9900
O3—C4	1.4308 (18)	C4—H4B	0.9900
O3—H3	0.84 (1)	C5—C6	1.519 (2)
O4—C6	1.4212 (17)	C5—H5A	0.9900
O4—H4	0.83 (1)	C5—H5B	0.9900
N1—C2	1.4836 (18)	C6—H6A	0.9900
N1—C5	1.4839 (18)	C6—H6B	0.9900

O1—Zn1—O1ⁱ	180.0	N1—C2—H2A	108.7
O1—Zn1—O3ⁱ	91.59 (4)	C1—C2—H2A	108.7
O1ⁱ—Zn1—O3ⁱ	88.41 (4)	N1—C2—H2B	108.7
O1—Zn1—O3	88.41 (4)	C1—C2—H2B	108.7
O1ⁱ—Zn1—O3	91.59 (4)	H2A—C2—H2B	107.6
O3ⁱ—Zn1—O3	180.0	N1—C3—C4	110.98 (12)
O1—Zn1—N1ⁱ	97.12 (4)	N1—C3—H3A	109.4
O1ⁱ—Zn1—N1ⁱ	82.88 (4)	C4—C3—H3A	109.4
O3ⁱ—Zn1—N1ⁱ	82.74 (4)	N1—C3—H3B	109.4
O3—Zn1—N1ⁱ	97.26 (4)	C4—C3—H3B	109.4
O1—Zn1—N1	82.88 (4)	H3A—C3—H3B	108.0
O1ⁱ—Zn1—N1	97.12 (4)	O3—C4—C3	110.24 (12)
O3ⁱ—Zn1—N1	97.26 (4)	O3—C4—H4A	109.6
O3—Zn1—N1	82.74 (4)	C3—C4—H4A	109.6
N1ⁱ—Zn1—N1	180.0	O3—C4—H4B	109.6
C1—O1—Zn1	115.48 (9)	C3—C4—H4B	109.6
C4—O3—Zn1	109.91 (8)	H4A—C4—H4B	108.1
C4—O3—H3	108.3 (16)	N1—C5—C6	115.44 (12)
Zn1—O3—H3	118.6 (16)	N1—C5—H5A	108.4
C6—O4—H4	105.4 (17)	C6—C5—H5A	108.4
C2—N1—C5	112.49 (11)	N1—C5—H5B	108.4
C2—N1—C3	112.67 (11)	C6—C5—H5B	108.4
C5—N1—C3	111.57 (11)	H5A—C5—H5B	107.5
C2—N1—Zn1	106.95 (8)	O4—C6—C5	106.39 (12)
C5—N1—Zn1	109.26 (9)	O4—C6—H6A	110.5
C3—N1—Zn1	103.34 (9)	C5—C6—H6A	110.5
O2—C1—O1	124.08 (13)	O4—C6—H6B	110.5
O2—C1—C2	116.06 (13)	C5—C6—H6B	110.5
O1—C1—C2	119.86 (13)	H6A—C6—H6B	108.6
N1—C2—C1	114.08 (12)

O3ⁱ—Zn1—O1—C1	−92.62 (10)	O3ⁱ—Zn1—N1—C3	−157.45 (8)
O3—Zn1—O1—C1	87.38 (10)	O3—Zn1—N1—C3	22.55 (8)
N1ⁱ—Zn1—O1—C1	−175.50 (10)	Zn1—O1—C1—O2	178.78 (12)
N1—Zn1—O1—C1	4.50 (10)	Zn1—O1—C1—C2	−0.37 (17)
O1—Zn1—O3—C4	−78.86 (9)	C5—N1—C2—C1	128.95 (13)
O1ⁱ—Zn1—O3—C4	101.14 (9)	C3—N1—C2—C1	−103.88 (14)
N1ⁱ—Zn1—O3—C4	−175.83 (9)	Zn1—N1—C2—C1	8.99 (14)
N1—Zn1—O3—C4	4.17 (9)	O2—C1—C2—N1	174.38 (12)
O1—Zn1—N1—C2	−7.26 (9)	O1—C1—C2—N1	−6.4 (2)
O1ⁱ—Zn1—N1—C2	172.74 (9)	C2—N1—C3—C4	68.96 (15)
O3ⁱ—Zn1—N1—C2	83.44 (9)	C5—N1—C3—C4	−163.38 (12)
O3—Zn1—N1—C2	−96.56 (9)	Zn1—N1—C3—C4	−46.10 (13)
O1—Zn1—N1—C5	−129.27 (9)	Zn1—O3—C4—C3	−30.45 (14)
O1ⁱ—Zn1—N1—C5	50.73 (9)	N1—C3—C4—O3	53.60 (16)
O3ⁱ—Zn1—N1—C5	−38.57 (9)	C2—N1—C5—C6	68.31 (16)
O3—Zn1—N1—C5	141.43 (9)	C3—N1—C5—C6	−59.44 (16)
O1—Zn1—N1—C3	111.84 (9)	Zn1—N1—C5—C6	−173.08 (10)
O1ⁱ—Zn1—N1—C3	−68.16 (9)	N1—C5—C6—O4	179.67 (11)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2ⁱⁱ	0.84 (1)	1.85 (1)	2.651 (2)	161 (2)
O4—H4···O2ⁱⁱⁱ	0.83 (1)	1.89 (1)	2.715 (2)	178 (3)

Symmetry codes: (ii) −x+1, y+1/2, −z+3/2; (iii) −x, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Zn(C₆H₁₂NO₄)₂]
M_r	389.70
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	9.7863 (7), 11.3715 (8), 7.3462 (5)
β (°)	109.1495 (8)
V (Å³)	772.28 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.64
Crystal size (mm)	0.25 × 0.20 × 0.15

Data collection
Diffractometer	Bruker SMART APEX
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.685, 0.792
No. of measured, independent and observed [I > 2σ(I)] reflections	7174, 1773, 1634
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.062, 1.12
No. of reflections	1773
No. of parameters	114
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.35

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2ⁱ	0.84 (1)	1.85 (1)	2.651 (2)	161 (2)
O4—H4···O2ⁱⁱ	0.83 (1)	1.89 (1)	2.715 (2)	178 (3)

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) −x, y+1/2, −z+1/2.

Acknowledgements

We thank the University of Malaya (grant No. RG020/09AFR) for supporting this study.

References

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