Bis{2-[bis-(2-hy-droxy-eth-yl)amino]-acetato-κO,N,O'}zinc(II).

In the crystal structure of the zinc(II) complex of bicine, [Zn(C(6)H(12)NO(4))(2)], the deprotonated amino acid O,N,O'-chelates to the metal atom through a carboxyl-ate O atom, a hy-droxy O atom and the N atom, the three atoms occupying fac positions of the distorted octa-hedron surrounding the metal atom. The metal atom lies on a center of inversion. The uncoordinated carboxyl-ate O atom is hydrogen bonded to the hy-droxy groups of adjacent mol-ecules, 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 = 389.70

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.021

wR(F 2) = 0.062

S = 1.12

1773 reflections

114 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.35 e Å−3

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 ▶).

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043217/xu5062Isup2.hkl

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

[Zn(C6H12NO4)2]	F(000) = 408
Mr = 389.70	Dx = 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

Bruker SMART APEX diffractometer	1773 independent reflections
Radiation source: fine-focus sealed tube	1634 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω scans	θmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.685, Tmax = 0.792	k = −14→14
7174 measured reflections	l = −9→9

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(Fo2) + (0.0283P)2 + 0.4612P] where P = (Fo2 + 2Fc2)/3
1773 reflections	(Δ/σ)max = 0.001
114 parameters	Δρmax = 0.43 e Å−3
2 restraints	Δρmin = −0.35 e Å−3

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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)

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) ; (ii) .