Bis{N-[2-hy­droxy-1,1-bis­(hy­droxy­methyl)eth­yl]glycinato-κ3O,N,O′}iron(II)

Jiang, N.; Hou, J.-J.

doi:10.1107/S160053681401397X

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 7| July 2014| Page m274

https://doi.org/10.1107/S160053681401397X

Open

access

Bis{N-[2-hydroxy-1,1-bis(hydroxymethyl)ethyl]glycinato-κ³O,N,O′}iron(II)

Ning Jiang ^a and Juan-Juan Hou ^a ^*

^aSchool of Chemistry and Material Science, Shanxi Normal University, Linfen 041004, People's Republic of China
^*Correspondence e-mail: hjjtbq@163.com

(Received 3 June 2014; accepted 14 June 2014; online 21 June 2014)

In the title compound, [Fe(C₆H₁₂NO₅)₂], the Fe^II ion lies on an inversion center and is coordinated by two N atoms and four O atoms from two tridentate N-[2-hydroxy-1,1-bis(hydroxymethyl)ethyl]glycine ligands, forming a slightly distorted octahedral coordination environment. In the crystal, O—H⋯O, O—H⋯N and weak C—H⋯O hydrogen bonds link molecules, forming a three-dimensional network.

Keywords: crystal structure.

Related literature

For background to the applications of tripodal alcohols as single-molecule magnets, see: Pilawa et al. (1998 ); Brechin (2005 ); Murugesu et al. (2005 ).

Experimental

Crystal data

[Fe(C₆H₁₂NO₅)₂]
M_r = 412.18
Monoclinic, P 2₁ /c
a = 8.8198 (7) Å
b = 9.0245 (7) Å
c = 12.3533 (7) Å
β = 127.224 (4)°
V = 782.94 (10) Å³
Z = 2
Mo Kα radiation
μ = 1.02 mm⁻¹
T = 298 K
0.19 × 0.16 × 0.08 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.829, T_max = 0.923
4000 measured reflections
1708 independent reflections
1230 reflections with I > 2σ(I)
R_int = 0.056

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.099
S = 1.04
1708 reflections
131 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2ⁱ	0.87 (2)	2.10 (2)	2.952 (4)	166 (3)
O3—H3A⋯O4ⁱⁱ	0.86 (2)	1.72 (2)	2.562 (4)	167 (5)
O1—H1B⋯O5ⁱⁱⁱ	0.85 (2)	1.96 (2)	2.804 (4)	174 (6)
O1—H1B⋯O4ⁱⁱⁱ	0.85 (2)	2.59 (5)	3.172 (4)	127 (4)
O2—H2C⋯O1ⁱⁱ	0.85 (2)	1.93 (2)	2.779 (4)	170 (5)
C5—H5B⋯O5^iv	0.97	2.56	3.452 (4)	153
C2—H2A⋯O1	0.97	2.56	3.184 (4)	122
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x-1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iv) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2006 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S160053681401397X/lh5715sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681401397X/lh5715Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S160053681401397X/lh5715Isup3.cdx

checkCIF report

Comment top

Tripodal alcohols have been used as poly-dentate ligands in combination with paramagnetic 3d transition metal ions leading to the formation of high nuclear clusters since the discovery of the phenomenon of single-molecule magnetism (Brechin, 2005; Murugesu et al., 2005; Pilawa et al., 1998). During our synthesis to form a poly-nuclear cluster using the N-[tris(hydroxymethyl)ethyl]glycine ligand the title compound was fortuitously obtained.

In the title molecule the Fe^II ion is located on an inversion center (Fig. 1). The Fe^II ion is in a slightly distorted octahedral coordination environment formed by two N atoms and four O atoms from two N-[tris(hydroxymethyl)ethyl]glycine ligands. In the crystal, classical O—H···O, O—H···N and weak C—H···O hydrogen bonds (Table 1) connect the molecules into a three-dimensional superamolecular architecture.

Related literature top

For background to the applications of tripodal alcohols as single-molecule magnets, see: Pilawa et al. (1998); Brechin (2005); Murugesu et al. (2005).

Experimental top

The title compound was synthesized hydrothermally under autogenous pressure. A mixture of FeSO₄ (0.028 g, 0.1 mmol), N-[tris(hydroxymethyl)ethyl]glycine (0.056 g, 0.3 mmol), methanol (3 ml), N,N'-dimethyl formamide (1 ml) and H₂O (2 ml), was stirred for 30 min and then sealed in a 15 ml Teflon-lined stainless container and heated to 358K for 60 h. After cooling to room temperature and subjected to filltration, colorless plates were recovered.

Structure description top

For background to the applications of tripodal alcohols as single-molecule magnets, see: Pilawa et al. (1998); Brechin (2005); Murugesu et al. (2005).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2006); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound showing 50% displacement ellipsoids. Unlabeled atoms are related by the symmetry operator (-x+1, -y+1, -z+1).

Bis{N-[2-hydroxy-1,1-bis(hydroxymethyl)ethyl]glycinato-κ³O,N,O'}iron(II) top

Crystal data top

[Fe(C₆H₁₂NO₅)₂]	F(000) = 432
M_r = 412.18	D_x = 1.748 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 621 reflections
a = 8.8198 (7) Å	θ = 2.9–21.9°
b = 9.0245 (7) Å	µ = 1.02 mm⁻¹
c = 12.3533 (7) Å	T = 298 K
β = 127.224 (4)°	Sheet, colorless
V = 782.94 (10) Å³	0.19 × 0.16 × 0.08 mm
Z = 2

Data collection top

Bruker SMART CCD diffractometer	1708 independent reflections
Radiation source: fine-focus sealed tube	1230 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.056
multi–scan	θ_max = 27.0°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −11→11
T_min = 0.829, T_max = 0.923	k = −11→11
4000 measured reflections	l = −15→15

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.034P)²] where P = (F_o² + 2F_c²)/3
1708 reflections	(Δ/σ)_max < 0.001
131 parameters	Δρ_max = 0.46 e Å⁻³
4 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

[Fe(C₆H₁₂NO₅)₂]	V = 782.94 (10) Å³
M_r = 412.18	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.8198 (7) Å	µ = 1.02 mm⁻¹
b = 9.0245 (7) Å	T = 298 K
c = 12.3533 (7) Å	0.19 × 0.16 × 0.08 mm
β = 127.224 (4)°

Data collection top

Bruker SMART CCD diffractometer	1708 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	1230 reflections with I > 2σ(I)
T_min = 0.829, T_max = 0.923	R_int = 0.056
4000 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	4 restraints
wR(F²) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.46 e Å⁻³
1708 reflections	Δρ_min = −0.39 e Å⁻³
131 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > 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.

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

	x	y	z	U_iso*/U_eq
Fe1	0.5000	0.5000	0.5000	0.01527 (19)
O1	−0.0265 (4)	0.7341 (3)	0.0516 (3)	0.0347 (7)
O2	0.0173 (4)	0.8369 (3)	0.3530 (3)	0.0355 (7)
O3	0.4719 (4)	0.7180 (3)	0.5354 (3)	0.0323 (7)
O4	0.6437 (4)	0.6393 (3)	0.2600 (3)	0.0356 (7)
O5	0.6619 (3)	0.5743 (3)	0.4408 (2)	0.0283 (6)
N1	0.2766 (4)	0.5686 (3)	0.2962 (3)	0.0209 (6)
C1	0.2121 (5)	0.7215 (4)	0.2983 (3)	0.0190 (8)
C2	0.3608 (5)	0.5508 (4)	0.2233 (3)	0.0237 (8)
H2A	0.2927	0.6132	0.1430	0.028*
H2B	0.3466	0.4488	0.1940	0.028*
C3	0.5700 (5)	0.5920 (4)	0.3128 (4)	0.0243 (8)
C4	0.1289 (5)	0.8101 (4)	0.1682 (4)	0.0276 (9)
H4A	0.0855	0.9056	0.1758	0.033*
H4B	0.2274	0.8276	0.1572	0.033*
C5	0.0626 (5)	0.6982 (4)	0.3222 (4)	0.0269 (8)
H5A	−0.0516	0.6556	0.2416	0.032*
H5B	0.1112	0.6298	0.3971	0.032*
C6	0.3822 (5)	0.8077 (4)	0.4165 (4)	0.0269 (8)
H6A	0.4712	0.8302	0.3973	0.032*
H6B	0.3396	0.9003	0.4299	0.032*
H1A	0.182 (4)	0.506 (3)	0.259 (3)	0.027 (10)*
H3A	0.514 (6)	0.773 (5)	0.605 (3)	0.078 (18)*
H1B	−0.126 (5)	0.787 (5)	0.014 (5)	0.10 (2)*
H2C	0.019 (7)	0.815 (5)	0.421 (4)	0.080 (19)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0159 (4)	0.0181 (3)	0.0101 (4)	0.0003 (3)	0.0069 (3)	0.0009 (3)
O1	0.0265 (16)	0.0462 (18)	0.0188 (15)	0.0048 (14)	0.0070 (14)	0.0003 (13)
O2	0.0443 (18)	0.0349 (16)	0.0402 (19)	0.0148 (13)	0.0323 (16)	0.0086 (14)
O3	0.0379 (17)	0.0292 (15)	0.0160 (15)	0.0004 (13)	0.0091 (14)	−0.0017 (12)
O4	0.0293 (15)	0.0513 (18)	0.0283 (16)	0.0014 (13)	0.0185 (14)	0.0135 (13)
O5	0.0234 (14)	0.0396 (15)	0.0174 (14)	0.0003 (12)	0.0100 (12)	0.0048 (12)
N1	0.0203 (16)	0.0195 (16)	0.0220 (17)	−0.0026 (13)	0.0123 (15)	−0.0040 (13)
C1	0.0192 (18)	0.0201 (18)	0.0148 (19)	0.0020 (14)	0.0087 (16)	0.0019 (14)
C2	0.0213 (19)	0.0286 (19)	0.018 (2)	0.0028 (15)	0.0103 (17)	−0.0004 (15)
C3	0.026 (2)	0.0218 (19)	0.024 (2)	0.0015 (16)	0.0141 (18)	0.0035 (16)
C4	0.027 (2)	0.029 (2)	0.022 (2)	0.0025 (17)	0.0123 (19)	0.0029 (17)
C5	0.027 (2)	0.031 (2)	0.025 (2)	0.0050 (17)	0.0166 (19)	0.0038 (17)
C6	0.025 (2)	0.027 (2)	0.023 (2)	−0.0003 (16)	0.0121 (18)	−0.0005 (17)

Geometric parameters (Å, º) top

Fe1—O3ⁱ	2.062 (3)	N1—C1	1.498 (4)
Fe1—O3	2.062 (3)	N1—H1A	0.871 (18)
Fe1—O5ⁱ	2.071 (2)	C1—C4	1.527 (4)
Fe1—O5	2.071 (2)	C1—C6	1.529 (5)
Fe1—N1	2.145 (3)	C1—C5	1.531 (4)
Fe1—N1ⁱ	2.145 (3)	C2—C3	1.515 (5)
O1—C4	1.427 (4)	C2—H2A	0.9700
O1—H1B	0.850 (19)	C2—H2B	0.9700
O2—C5	1.433 (4)	C4—H4A	0.9700
O2—H2C	0.854 (19)	C4—H4B	0.9700
O3—C6	1.426 (4)	C5—H5A	0.9700
O3—H3A	0.855 (19)	C5—H5B	0.9700
O4—C3	1.242 (4)	C6—H6A	0.9700
O5—C3	1.277 (4)	C6—H6B	0.9700
N1—C2	1.482 (4)

O3ⁱ—Fe1—O3	180.000 (1)	N1—C1—C5	104.9 (3)
O3ⁱ—Fe1—O5ⁱ	87.88 (10)	C4—C1—C5	110.7 (3)
O3—Fe1—O5ⁱ	92.12 (10)	C6—C1—C5	110.3 (3)
O3ⁱ—Fe1—O5	92.12 (10)	N1—C2—C3	111.5 (3)
O3—Fe1—O5	87.88 (10)	N1—C2—H2A	109.3
O5ⁱ—Fe1—O5	180.0	C3—C2—H2A	109.3
O3ⁱ—Fe1—N1	99.75 (10)	N1—C2—H2B	109.3
O3—Fe1—N1	80.25 (10)	C3—C2—H2B	109.3
O5ⁱ—Fe1—N1	99.68 (10)	H2A—C2—H2B	108.0
O5—Fe1—N1	80.32 (10)	O4—C3—O5	123.4 (3)
O3ⁱ—Fe1—N1ⁱ	80.25 (10)	O4—C3—C2	119.6 (3)
O3—Fe1—N1ⁱ	99.75 (10)	O5—C3—C2	117.0 (3)
O5ⁱ—Fe1—N1ⁱ	80.32 (10)	O1—C4—C1	111.5 (3)
O5—Fe1—N1ⁱ	99.68 (10)	O1—C4—H4A	109.3
N1—Fe1—N1ⁱ	180.000 (1)	C1—C4—H4A	109.3
C4—O1—H1B	109 (4)	O1—C4—H4B	109.3
C5—O2—H2C	102 (3)	C1—C4—H4B	109.3
C6—O3—Fe1	112.7 (2)	H4A—C4—H4B	108.0
C6—O3—H3A	109 (3)	O2—C5—C1	110.0 (3)
Fe1—O3—H3A	137 (3)	O2—C5—H5A	109.7
C3—O5—Fe1	114.9 (2)	C1—C5—H5A	109.7
C2—N1—C1	116.4 (3)	O2—C5—H5B	109.7
C2—N1—Fe1	103.9 (2)	C1—C5—H5B	109.7
C1—N1—Fe1	109.5 (2)	H5A—C5—H5B	108.2
C2—N1—H1A	106 (2)	O3—C6—C1	107.9 (3)
C1—N1—H1A	111 (2)	O3—C6—H6A	110.1
Fe1—N1—H1A	110 (2)	C1—C6—H6A	110.1
N1—C1—C4	114.2 (3)	O3—C6—H6B	110.1
N1—C1—C6	108.8 (3)	C1—C6—H6B	110.1
C4—C1—C6	107.9 (3)	H6A—C6—H6B	108.4

O5ⁱ—Fe1—O3—C6	−120.1 (2)	Fe1—N1—C1—C6	32.2 (3)
O5—Fe1—O3—C6	59.9 (2)	C2—N1—C1—C5	156.7 (3)
N1—Fe1—O3—C6	−20.6 (2)	Fe1—N1—C1—C5	−85.9 (3)
N1ⁱ—Fe1—O3—C6	159.4 (2)	C1—N1—C2—C3	83.5 (4)
O3ⁱ—Fe1—O5—C3	84.2 (2)	Fe1—N1—C2—C3	−37.0 (3)
O3—Fe1—O5—C3	−95.8 (2)	Fe1—O5—C3—O4	178.2 (3)
N1—Fe1—O5—C3	−15.3 (2)	Fe1—O5—C3—C2	−2.4 (4)
N1ⁱ—Fe1—O5—C3	164.7 (2)	N1—C2—C3—O4	−152.0 (3)
O3ⁱ—Fe1—N1—C2	−62.5 (2)	N1—C2—C3—O5	28.6 (4)
O3—Fe1—N1—C2	117.5 (2)	N1—C1—C4—O1	56.5 (4)
O5ⁱ—Fe1—N1—C2	−152.0 (2)	C6—C1—C4—O1	177.6 (3)
O5—Fe1—N1—C2	28.0 (2)	C5—C1—C4—O1	−61.6 (4)
O3ⁱ—Fe1—N1—C1	172.4 (2)	N1—C1—C5—O2	168.6 (3)
O3—Fe1—N1—C1	−7.6 (2)	C4—C1—C5—O2	−67.7 (4)
O5ⁱ—Fe1—N1—C1	82.9 (2)	C6—C1—C5—O2	51.6 (4)
O5—Fe1—N1—C1	−97.1 (2)	Fe1—O3—C6—C1	43.9 (3)
C2—N1—C1—C4	35.4 (4)	N1—C1—C6—O3	−49.6 (3)
Fe1—N1—C1—C4	152.8 (2)	C4—C1—C6—O3	−174.0 (3)
C2—N1—C1—C6	−85.3 (3)	C5—C1—C6—O3	65.0 (3)

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
N1—H1A···O2ⁱⁱ	0.87 (2)	2.10 (2)	2.952 (4)	166 (3)
O3—H3A···O4ⁱⁱⁱ	0.86 (2)	1.72 (2)	2.562 (4)	167 (5)
O1—H1B···O5^iv	0.85 (2)	1.96 (2)	2.804 (4)	174 (6)
O1—H1B···O4^iv	0.85 (2)	2.59 (5)	3.172 (4)	127 (4)
O2—H2C···O1ⁱⁱⁱ	0.85 (2)	1.93 (2)	2.779 (4)	170 (5)
C5—H5B···O5ⁱ	0.97	2.56	3.452 (4)	153
C2—H2A···O1	0.97	2.56	3.184 (4)	122

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2ⁱ	0.871 (18)	2.10 (2)	2.952 (4)	166 (3)
O3—H3A···O4ⁱⁱ	0.855 (19)	1.72 (2)	2.562 (4)	167 (5)
O1—H1B···O5ⁱⁱⁱ	0.850 (19)	1.96 (2)	2.804 (4)	174 (6)
O1—H1B···O4ⁱⁱⁱ	0.850 (19)	2.59 (5)	3.172 (4)	127 (4)
O2—H2C···O1ⁱⁱ	0.854 (19)	1.93 (2)	2.779 (4)	170 (5)
C5—H5B···O5^iv	0.97	2.56	3.452 (4)	152.8
C2—H2A···O1	0.97	2.56	3.184 (4)	122.3

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

Acknowledgements

The authors thank the National Science Foundation (21201114).

References

Brandenburg, K. & Putz, H. (2006). DIAMOND. Crystal Impact, Bonn, Germany. Google Scholar
Brechin, E. K. (2005). Chem. Commun. pp. 5141–5153. Web of Science CrossRef Google Scholar
Bruker (2007). SAINT-Plus, SMART and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Murugesu, M., Wernsdorfer, W., Abboud, K. A. & Christou, G. (2005). Angew. Chem. Int. Ed. 44, 892–896. Web of Science CSD CrossRef CAS Google Scholar
Pilawa, B., Kelemen, M. T., Wanka, S., Geisselmann, A. & Barra, A. L. (1998). Europhys. Lett. 43, 7–12. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.