Poly[di-μ-glycinato-copper(II)]: a two-dimensional coordination polymer.

The title coordination polymer, [Cu(C(2)H(4)NO(2))(2)](n), is two-dimensional and consists of a distorted octa-hedral copper coordination polyhedron with two bidentate glycine ligands chelating the metal through the O and N atoms in a trans-square-planar configuration. The two axial coordination sites are occupied by carbonyl O atoms of neighbouring glycine mol-ecules. The Cu-O distances for the axial O atoms [2.648 (2) and 2.837 (2) Å] are considerably longer than both the Cu-O [1.9475 (17) and 1.9483 (18) Å] and Cu-N [1.988 (2) and 1.948 (2) Å] distances in the equatorial plane, which indicates a strong Jahn-Teller effect. In the crystal, the two-dimensional networks are arranged parallel to (001) and are linked via N-H⋯O hydrogen bonds, forming a three-dimensional arrangement.

Related literature

For the first work on cadmium glycinato complexes, see: Low et al. (1959 ▶). For similar mixed-metal glycinato complexes with copper(II), see: Papavinasam (1991 ▶); Davies et al. (2003 ▶); Low et al. (1959 ▶); Bi et al. (2006 ▶); Zhang et al. (2005 ▶). For further studies on cadmium–glycinato complexes, see: Barrie et al. (1993 ▶). For the properties and structure of a three-dimensional copper–glycinate polymer, see: Chen et al. (2009 ▶). For the synthesis of [NaCu6(gly)3(ClO4)3(H2O)](ClO4)2, see: Aromi et al. (2008 ▶).

Experimental

Crystal data

[Cu(C2H4NO2)2]

M = 211.66

Monoclinic,

a = 9.4265 (19) Å

b = 5.1159 (10) Å

c = 13.912 (3) Å

β = 107.36 (3)°

V = 640.4 (2) Å3

Z = 4

Mo Kα radiation

μ = 3.37 mm−1

T = 298 K

0.21 × 0.15 × 0.09 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-SHAPE and X-RED; Stoe & Cie, 2009 ▶) T min = 0.549, T max = 0.692

9012 measured reflections

1876 independent reflections

1561 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.075

S = 1.03

1876 reflections

116 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.58 e Å−3

Data collection: X-AREA (Stoe & Cie, 2009 ▶); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811031503/su2280sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811031503/su2280Isup2.hkl

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

[Cu(C2H4NO2)2]	F(000) = 428
Mr = 211.66	Dx = 2.195 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5867 reflections
a = 9.4265 (19) Å	θ = 2.3–30.5°
b = 5.1159 (10) Å	µ = 3.37 mm−1
c = 13.912 (3) Å	T = 298 K
β = 107.36 (3)°	Block, blue
V = 640.4 (2) Å3	0.21 × 0.15 × 0.09 mm
Z = 4

Stoe IPDS 2 diffractometer	1876 independent reflections
Radiation source: fine-focus sealed tube	1561 reflections with I > 2σ(I)
graphite	Rint = 0.048
Detector resolution: 6.67 pixels mm-1	θmax = 30.0°, θmin = 2.3°
rotation method scans	h = −13→13
Absorption correction: integration (X-SHAPE and X-RED; Stoe & Cie, 2009)	k = −7→6
Tmin = 0.549, Tmax = 0.692	l = −19→17
9012 measured reflections

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.075	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0447P)2] where P = (Fo2 + 2Fc2)/3
1876 reflections	(Δ/σ)max = 0.001
116 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.58 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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.

	x	y	z	Uiso*/Ueq
Cu1	−0.00228 (3)	0.02678 (5)	0.26465 (2)	0.0301 (1)
O1	−0.17587 (17)	−0.1989 (3)	0.21922 (12)	0.0270 (4)
O2	−0.3924 (2)	−0.2410 (4)	0.10081 (14)	0.0408 (6)
O3	0.17471 (18)	0.2461 (3)	0.30307 (13)	0.0317 (4)
O4	0.41730 (18)	0.2283 (4)	0.38098 (15)	0.0392 (5)
N1	−0.1151 (2)	0.2642 (4)	0.15535 (16)	0.0283 (5)
N2	0.1137 (2)	−0.2140 (4)	0.37098 (17)	0.0302 (6)
C1	−0.2742 (2)	−0.1247 (4)	0.13882 (17)	0.0260 (6)
C2	−0.2384 (3)	0.1181 (4)	0.08778 (17)	0.0304 (6)
C3	0.2916 (2)	0.1351 (4)	0.36051 (16)	0.0253 (5)
C4	0.2694 (2)	−0.1268 (4)	0.40529 (17)	0.0282 (6)
H1A	0.112 (5)	−0.378 (10)	0.340 (3)	0.076 (13)*
H1B	0.082 (4)	−0.233 (7)	0.418 (3)	0.045 (9)*
H2A	−0.21240	0.06770	0.02790	0.0360*
H2B	−0.32560	0.22930	0.06700	0.0360*
H3A	−0.153 (4)	0.393 (7)	0.184 (2)	0.045 (9)*
H3B	−0.061 (4)	0.342 (8)	0.124 (3)	0.061 (11)*
H4A	0.33140	−0.25670	0.38670	0.0340*
H4B	0.30110	−0.11300	0.47810	0.0340*

	U11	U22	U33	U12	U13	U23
Cu1	0.0249 (1)	0.0214 (1)	0.0380 (2)	−0.0026 (1)	−0.0001 (1)	0.0078 (1)
O1	0.0262 (7)	0.0191 (7)	0.0334 (8)	−0.0016 (5)	0.0052 (6)	0.0030 (6)
O2	0.0375 (9)	0.0391 (10)	0.0389 (10)	−0.0142 (7)	0.0010 (7)	0.0043 (7)
O3	0.0277 (7)	0.0216 (7)	0.0408 (9)	−0.0028 (6)	0.0028 (6)	0.0046 (6)
O4	0.0275 (8)	0.0350 (9)	0.0510 (11)	−0.0060 (7)	0.0057 (7)	0.0016 (8)
N1	0.0274 (9)	0.0214 (8)	0.0340 (10)	−0.0019 (7)	0.0062 (7)	0.0055 (7)
N2	0.0291 (9)	0.0253 (9)	0.0331 (11)	−0.0023 (7)	0.0046 (8)	0.0068 (8)
C1	0.0282 (10)	0.0234 (9)	0.0262 (10)	−0.0011 (7)	0.0080 (8)	−0.0020 (8)
C2	0.0351 (11)	0.0263 (10)	0.0264 (11)	−0.0053 (8)	0.0041 (8)	0.0017 (8)
C3	0.0267 (9)	0.0238 (9)	0.0246 (10)	−0.0018 (7)	0.0066 (8)	−0.0025 (7)
C4	0.0279 (10)	0.0272 (10)	0.0272 (11)	0.0017 (8)	0.0049 (8)	0.0043 (8)

Cu1—O1	1.9475 (17)	N2—C4	1.471 (3)
Cu1—O3	1.9483 (18)	N1—H3B	0.86 (4)
Cu1—N1	1.988 (2)	N1—H3A	0.90 (4)
Cu1—N2	1.984 (2)	N2—H1A	0.94 (5)
Cu1—O2i	2.648 (2)	N2—H1B	0.80 (4)
Cu1—O4ii	2.837 (2)	C1—C2	1.518 (3)
O1—C1	1.279 (3)	C3—C4	1.518 (3)
O2—C1	1.234 (3)	C2—H2A	0.9700
O3—C3	1.284 (3)	C2—H2B	0.9700
O4—C3	1.229 (3)	C4—H4A	0.9700
N1—C2	1.463 (3)	C4—H4B	0.9700
O1—Cu1—O3	176.59 (8)	H3A—N1—H3B	105 (4)
O1—Cu1—N1	84.73 (8)	C4—N2—H1A	107 (3)
O1—Cu1—N2	95.55 (8)	Cu1—N2—H1A	106 (3)
O1—Cu1—O2i	92.26 (7)	Cu1—N2—H1B	115 (3)
O1—Cu1—O4ii	80.68 (7)	C4—N2—H1B	111 (3)
O3—Cu1—N1	94.41 (8)	H1A—N2—H1B	108 (4)
O3—Cu1—N2	85.22 (8)	O2—C1—C2	119.5 (2)
O2i—Cu1—O3	91.07 (7)	O1—C1—O2	123.9 (2)
O3—Cu1—O4ii	96.01 (7)	O1—C1—C2	116.60 (19)
N1—Cu1—N2	178.27 (9)	N1—C2—C1	111.24 (19)
O2i—Cu1—N1	92.22 (8)	O3—C3—O4	124.2 (2)
O4ii—Cu1—N1	89.04 (8)	O3—C3—C4	116.60 (18)
O2i—Cu1—N2	89.48 (8)	O4—C3—C4	119.3 (2)
O4ii—Cu1—N2	89.32 (8)	N2—C4—C3	112.39 (18)
O2i—Cu1—O4ii	172.69 (7)	N1—C2—H2A	109.00
Cu1—O1—C1	115.30 (14)	N1—C2—H2B	109.00
Cu1iii—O2—C1	113.23 (15)	C1—C2—H2A	109.00
Cu1—O3—C3	114.93 (14)	C1—C2—H2B	109.00
Cu1iv—O4—C3	120.10 (16)	H2A—C2—H2B	108.00
Cu1—N1—C2	108.68 (14)	N2—C4—H4A	109.00
Cu1—N2—C4	109.16 (15)	N2—C4—H4B	109.00
C2—N1—H3A	108 (2)	C3—C4—H4A	109.00
Cu1—N1—H3A	107.6 (18)	C3—C4—H4B	109.00
Cu1—N1—H3B	114 (3)	H4A—C4—H4B	108.00
C2—N1—H3B	113 (3)
N1—Cu1—O1—C1	6.99 (16)	N2—Cu1—O2i—C1i	−157.43 (17)
N2—Cu1—O1—C1	−171.29 (16)	O1—Cu1—O4ii—C3ii	−133.24 (18)
O2i—Cu1—O1—C1	99.01 (15)	O3—Cu1—O4ii—C3ii	47.61 (18)
O4ii—Cu1—O1—C1	−82.90 (15)	N1—Cu1—O4ii—C3ii	141.95 (18)
N1—Cu1—O3—C3	−166.00 (16)	N2—Cu1—O4ii—C3ii	−37.51 (18)
N2—Cu1—O3—C3	12.30 (16)	Cu1—O1—C1—O2	−178.31 (18)
O2i—Cu1—O3—C3	101.69 (16)	Cu1—O1—C1—C2	3.1 (2)
O4ii—Cu1—O3—C3	−76.51 (16)	Cu1iii—O2—C1—O1	32.3 (3)
O1—Cu1—N1—C2	−14.98 (16)	Cu1iii—O2—C1—C2	−149.11 (17)
O3—Cu1—N1—C2	161.71 (16)	Cu1—O3—C3—O4	169.39 (19)
O2i—Cu1—N1—C2	−107.04 (16)	Cu1—O3—C3—C4	−11.0 (2)
O4ii—Cu1—N1—C2	65.75 (16)	Cu1iv—O4—C3—O3	−34.4 (3)
O1—Cu1—N2—C4	166.43 (15)	Cu1iv—O4—C3—C4	146.03 (16)
O3—Cu1—N2—C4	−10.23 (15)	Cu1—N1—C2—C1	19.8 (2)
O2i—Cu1—N2—C4	−101.35 (15)	Cu1—N2—C4—C3	7.4 (2)
O4ii—Cu1—N2—C4	85.86 (15)	O1—C1—C2—N1	−15.8 (3)
O1—Cu1—O2i—C1i	−61.90 (17)	O2—C1—C2—N1	165.5 (2)
O3—Cu1—O2i—C1i	117.36 (17)	O3—C3—C4—N2	2.1 (3)
N1—Cu1—O2i—C1i	22.91 (17)	O4—C3—C4—N2	−178.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1A···O3v	0.94 (5)	2.12 (5)	3.029 (3)	162 (4)
N2—H1B···O2vi	0.80 (4)	2.49 (4)	3.223 (3)	154 (4)
N1—H3A···O1vii	0.90 (4)	2.17 (4)	2.994 (3)	152 (3)
N1—H3A···O1i	0.90 (4)	2.44 (4)	3.003 (3)	121 (3)
N1—H3B···O4iv	0.86 (4)	2.41 (4)	3.152 (3)	145 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1A⋯O3i	0.94 (5)	2.12 (5)	3.029 (3)	162 (4)
N2—H1B⋯O2ii	0.80 (4)	2.49 (4)	3.223 (3)	154 (4)
N1—H3A⋯O1iii	0.90 (4)	2.17 (4)	2.994 (3)	152 (3)
N1—H3A⋯O1iv	0.90 (4)	2.44 (4)	3.003 (3)	121 (3)
N1—H3B⋯O4v	0.86 (4)	2.41 (4)	3.152 (3)	145 (3)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .