catena-Poly[[[aqua-(glycine-κO)lithium]-μ-glycine-κ(2) O:O'] bromide].

In the title coordination polymer, {[Li(C2H5NO2)2(H2O)]Br} n , the Li(+) cation is coordinated by three carboxyl-ate O atoms of zwitterionic glycine mol-ecules and by a water mol-ecule, forming a distorted tetra-hedral geometry. One of the two glycine mol-ecules bridges neighbouring complexes, forming an infinite chain parallel to the c axis. Polymeric chains are further linked by extensive hydrogen bonds involving the Br(-) anions and glycine and water mol-ecules, producing a three-dimensional network.

Related literature

For hydrogen-bonding motifs, see Bernstein et al. (1995 ▶). For glycine polymorphs, see: Marsh (1958 ▶); Iitaka (1960 ▶, 1961 ▶). For glycine with halogen and metal halogenides, see: Fleck (2008 ▶). For related structures, see: Müller et al. (1994 ▶); Baran et al. (2003 ▶, 2009 ▶); Fleck & Bohatý (2004 ▶); Fleck et al. (2006 ▶). For head-to-tail hydrogen bonds, see: Sharma et al. (2006 ▶); Selvaraj et al. (2007 ▶).

Experimental

Crystal data

[Li(C2H5NO2)2(H2O)]Br

M = 255.01

Monoclinic,

a = 7.5396 (6) Å

b = 17.4173 (14) Å

c = 8.2726 (12) Å

β = 118.138 (7)°

V = 957.96 (18) Å3

Z = 4

Mo Kα radiation

μ = 4.28 mm−1

T = 173 K

0.61 × 0.30 × 0.30 mm

Data collection

STOE IPDS diffractometer

Absorption correction: multi-scan (MULscanABS in PLATON; Spek, 2009 ▶) T min = 0.217, T max = 0.277

7515 measured reflections

1847 independent reflections

1520 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.021

wR(F 2) = 0.051

S = 0.96

1847 reflections

151 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.55 e Å−3

Δρmin = −0.26 e Å−3

Data collection: EXPOSE in IPDS (Stoe & Cie, 2000 ▶); cell refinement: CELL in IPDS; data reduction: INTEGRATE in IPDS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812050660/aa2077sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812050660/aa2077Isup2.hkl

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

[Li(C2H5NO2)2(H2O)]Br	F(000) = 512
Mr = 255.01	Dx = 1.768 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7161 reflections
a = 7.5396 (6) Å	θ = 2.3–26.0°
b = 17.4173 (14) Å	µ = 4.28 mm−1
c = 8.2726 (12) Å	T = 173 K
β = 118.138 (7)°	Rod, colourless
V = 957.96 (18) Å3	0.61 × 0.30 × 0.30 mm
Z = 4

STOE IPDS diffractometer	1847 independent reflections
Radiation source: fine-focus sealed tube	1520 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
phi rotation scans	θmax = 26.0°, θmin = 2.3°
Absorption correction: multi-scan (MULscanABS in PLATON; Spek, 2009)	h = −9→9
Tmin = 0.217, Tmax = 0.277	k = −21→21
7515 measured reflections	l = −10→10

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.021	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.051	w = 1/[σ2(Fo2) + (0.0317P)2] where P = (Fo2 + 2Fc2)/3
S = 0.96	(Δ/σ)max = 0.001
1847 reflections	Δρmax = 0.55 e Å−3
151 parameters	Δρmin = −0.26 e Å−3
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0097 (8)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2sigma(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
O1	0.4191 (2)	0.89555 (8)	0.8413 (2)	0.0210 (3)
O2	0.1743 (3)	0.80884 (9)	0.7211 (2)	0.0250 (4)
O1W	0.0182 (3)	0.65924 (9)	0.4468 (2)	0.0218 (4)
H1	0.075 (4)	0.6666 (14)	0.385 (4)	0.027 (7)*
H2	0.084 (4)	0.6254 (14)	0.522 (4)	0.043 (9)*
O3	−0.1525 (3)	0.81668 (8)	0.1971 (2)	0.0270 (4)
O4	−0.2535 (2)	0.80493 (8)	0.4080 (2)	0.0217 (3)
N1	0.5965 (3)	0.84975 (12)	0.6419 (3)	0.0205 (4)
H1A	0.643 (4)	0.8360 (15)	0.559 (4)	0.031 (7)*
H1B	0.702 (5)	0.8395 (17)	0.755 (5)	0.038 (8)*
H1C	0.580 (5)	0.899 (2)	0.631 (4)	0.047 (9)*
N2	−0.2448 (3)	0.96593 (11)	0.1353 (3)	0.0174 (4)
H2A	−0.129 (5)	0.9644 (14)	0.156 (4)	0.025 (7)*
H2B	−0.323 (4)	0.9429 (15)	0.027 (4)	0.029 (7)*
H2C	−0.284 (4)	1.0168 (17)	0.126 (4)	0.035 (8)*
C1	0.3295 (3)	0.84132 (11)	0.7358 (3)	0.0153 (4)
C2	0.4092 (3)	0.81116 (11)	0.6103 (3)	0.0174 (4)
H2E	0.4342	0.7553	0.6307	0.021*
H2F	0.3062	0.8189	0.4812	0.021*
C3	−0.2198 (3)	0.84265 (12)	0.2952 (3)	0.0166 (4)
C4	−0.2679 (4)	0.92762 (12)	0.2840 (3)	0.0204 (5)
H4A	−0.4078	0.9343	0.2624	0.025*
H4B	−0.1772	0.9523	0.4025	0.025*
Li1	−0.0369 (6)	0.7388 (2)	0.5754 (5)	0.0196 (8)
Br1	0.24155 (3)	0.968012 (12)	0.27597 (3)	0.02208 (9)

	U11	U22	U33	U12	U13	U23
O1	0.0197 (8)	0.0202 (8)	0.0247 (9)	−0.0040 (6)	0.0118 (7)	−0.0074 (6)
O2	0.0244 (9)	0.0289 (8)	0.0290 (10)	−0.0120 (7)	0.0186 (8)	−0.0097 (7)
O1W	0.0316 (9)	0.0191 (8)	0.0248 (10)	0.0070 (7)	0.0217 (9)	0.0058 (7)
O3	0.0410 (10)	0.0198 (7)	0.0349 (10)	0.0062 (7)	0.0300 (9)	0.0011 (7)
O4	0.0254 (8)	0.0231 (7)	0.0223 (9)	0.0046 (6)	0.0159 (8)	0.0045 (6)
N1	0.0191 (11)	0.0237 (10)	0.0236 (12)	−0.0025 (8)	0.0142 (11)	−0.0050 (8)
N2	0.0149 (9)	0.0166 (9)	0.0213 (11)	0.0007 (8)	0.0089 (9)	−0.0015 (8)
C1	0.0165 (10)	0.0150 (9)	0.0145 (11)	0.0024 (8)	0.0073 (10)	0.0018 (8)
C2	0.0191 (11)	0.0168 (9)	0.0201 (12)	−0.0012 (8)	0.0123 (10)	−0.0027 (8)
C3	0.0128 (10)	0.0204 (10)	0.0157 (12)	0.0008 (8)	0.0061 (10)	−0.0019 (8)
C4	0.0253 (12)	0.0207 (11)	0.0211 (12)	0.0008 (9)	0.0158 (11)	−0.0023 (9)
Li1	0.023 (2)	0.0190 (16)	0.020 (2)	−0.0040 (14)	0.0125 (18)	−0.0022 (14)
Br1	0.01662 (13)	0.02188 (12)	0.02587 (15)	−0.00224 (9)	0.00846 (10)	−0.00292 (9)

O1—C1	1.247 (3)	N1—H1C	0.86 (3)
O2—C1	1.253 (3)	N2—C4	1.480 (3)
O2—Li1	1.915 (4)	N2—H2A	0.81 (3)
O1W—Li1	1.908 (4)	N2—H2B	0.90 (3)
O1W—H1	0.816 (17)	N2—H2C	0.93 (3)
O1W—H2	0.829 (18)	C1—C2	1.518 (3)
O3—C3	1.228 (3)	C2—H2E	0.9900
O3—Li1i	1.880 (4)	C2—H2F	0.9900
O4—C3	1.261 (3)	C3—C4	1.516 (3)
O4—Li1	1.944 (4)	C4—H4A	0.9900
N1—C2	1.472 (3)	C4—H4B	0.9900
N1—H1A	0.94 (3)	Li1—O3ii	1.880 (4)
N1—H1B	0.92 (4)
C1—O2—Li1	144.09 (18)	O3—C3—O4	126.0 (2)
Li1—O1W—H1	123.4 (18)	O3—C3—C4	118.73 (18)
Li1—O1W—H2	108 (2)	O4—C3—C4	115.30 (17)
H1—O1W—H2	106 (3)	O3—C3—Li1	96.65 (15)
C3—O3—Li1i	169.50 (19)	C4—C3—Li1	134.84 (17)
C3—O4—Li1	116.16 (16)	N2—C4—C3	111.84 (17)
C2—N1—H1A	114.4 (17)	N2—C4—H4A	109.2
C2—N1—H1B	113.0 (18)	C3—C4—H4A	109.2
H1A—N1—H1B	105 (3)	N2—C4—H4B	109.2
C2—N1—H1C	111 (2)	C3—C4—H4B	109.2
H1A—N1—H1C	105 (3)	H4A—C4—H4B	107.9
H1B—N1—H1C	108 (3)	O3ii—Li1—O1W	101.73 (17)
C4—N2—H2A	110 (2)	O3ii—Li1—O2	116.6 (2)
C4—N2—H2B	110.4 (17)	O1W—Li1—O2	118.6 (2)
H2A—N2—H2B	109 (3)	O3ii—Li1—O4	103.87 (18)
C4—N2—H2C	109.9 (18)	O1W—Li1—O4	111.3 (2)
H2A—N2—H2C	109 (2)	O2—Li1—O4	103.93 (17)
H2B—N2—H2C	108 (3)	O3ii—Li1—C3	128.00 (19)
O1—C1—O2	125.69 (19)	O1W—Li1—C3	99.35 (16)
O1—C1—C2	118.81 (18)	O2—Li1—C3	92.83 (15)
O2—C1—C2	115.49 (18)	O4—Li1—C3	24.36 (7)
N1—C2—C1	112.13 (17)	O3ii—Li1—H2	89.3 (7)
N1—C2—H2E	109.2	O1W—Li1—H2	20.0 (6)
C1—C2—H2E	109.2	O2—Li1—H2	112.4 (8)
N1—C2—H2F	109.2	O4—Li1—H2	130.3 (7)
C1—C2—H2F	109.2	C3—Li1—H2	119.3 (6)
H2E—C2—H2F	107.9
Li1—O2—C1—O1	168.2 (3)	C1—O2—Li1—C3	−72.0 (3)
Li1—O2—C1—C2	−10.9 (4)	C3—O4—Li1—O3ii	−172.65 (17)
O1—C1—C2—N1	3.5 (3)	C3—O4—Li1—O1W	−63.9 (2)
O2—C1—C2—N1	−177.3 (2)	C3—O4—Li1—O2	64.9 (2)
Li1i—O3—C3—O4	−14.7 (13)	O3—C3—Li1—O3ii	−133.0 (2)
Li1i—O3—C3—C4	165.1 (10)	O4—C3—Li1—O3ii	9.1 (2)
Li1i—O3—C3—Li1	14.2 (11)	C4—C3—Li1—O3ii	84.0 (3)
Li1—O4—C3—O3	49.0 (3)	O3—C3—Li1—O1W	−20.0 (2)
Li1—O4—C3—C4	−130.8 (2)	O4—C3—Li1—O1W	122.0 (2)
O3—C3—C4—N2	6.3 (3)	C4—C3—Li1—O1W	−163.0 (2)
O4—C3—C4—N2	−173.94 (19)	O3—C3—Li1—O2	99.58 (17)
Li1—C3—C4—N2	143.3 (2)	O4—C3—Li1—O2	−118.4 (2)
C1—O2—Li1—O3ii	152.4 (3)	C4—C3—Li1—O2	−43.4 (3)
C1—O2—Li1—O1W	30.3 (4)	O3—C3—Li1—O4	−142.0 (3)
C1—O2—Li1—O4	−93.9 (3)	C4—C3—Li1—O4	75.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O4iii	0.94 (3)	1.83 (3)	2.774 (2)	176 (3)
N1—H1B···O1Wiv	0.92 (4)	2.15 (4)	2.989 (3)	151 (2)
N1—H1C···Br1v	0.86 (3)	2.61 (3)	3.353 (2)	146 (3)
N2—H2A···Br1	0.81 (3)	2.48 (3)	3.283 (2)	170 (3)
N2—H2B···O1vi	0.90 (3)	2.00 (3)	2.833 (3)	153 (2)
N2—H2C···O1vii	0.93 (3)	1.92 (3)	2.797 (2)	157 (3)
O1W—H1···O2i	0.82 (2)	1.88 (2)	2.692 (2)	172 (3)
O1W—H2···Br1ii	0.83 (2)	2.48 (2)	3.2923 (17)	169 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O4i	0.94 (3)	1.83 (3)	2.774 (2)	176 (3)
N1—H1B⋯O1W ii	0.92 (4)	2.15 (4)	2.989 (3)	151 (2)
N1—H1C⋯Br1iii	0.86 (3)	2.61 (3)	3.353 (2)	146 (3)
N2—H2A⋯Br1	0.81 (3)	2.48 (3)	3.283 (2)	170 (3)
N2—H2B⋯O1iv	0.90 (3)	2.00 (3)	2.833 (3)	153 (2)
N2—H2C⋯O1v	0.93 (3)	1.92 (3)	2.797 (2)	157 (3)
O1W—H1⋯O2vi	0.82 (2)	1.88 (2)	2.692 (2)	172 (3)
O1W—H2⋯Br1vii	0.83 (2)	2.48 (2)	3.2923 (17)	169 (3)

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