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Acta Cryst. (2009). E65, m41    [ doi:10.1107/S1600536808041226 ]

Aqua(iminodiacetato-[kappa]3O,N,O')(1,10-phenanthroline-[kappa]2N,N')cobalt(II) monohydrate

H. L. Ng, C. H. Ng and S. W. Ng

Abstract top

The iminodiacetate dianion in the title compound, [Co(C4H5NO4)(C12H8N2)(H2O)]·H2O, chelates to the cobalt(II) atom, its N and two O atoms occupying the fac sites of the distorted octahedron around the metal atom. The metal atom is also chelated by the N-heterocycle. The dianion, and coordinated and uncoordinated water molecules interact through hydrogen bonds, generating a layer motif. The crystal studied was a racemic twin with a 0.62 (2):0.38 (2) domain ratio.

Related literature top

For structural examples of the N-heterocycle adducts of cobalt iminodiacetate, see: Su & Xu (2004); Xu et al. (1989).

Experimental top

An aqueous solution of cobalt(II) chloride (0.24 g, 1 mmol) was mixed with an aqueous solutin of disodium iminodiacetate monohydrate (0.20 g, 1 mmol); this was added to a water-methanol solution of 1,10-phenanthroline (0.20 g, 1 mmol). The solution was set aside for the growth of orange crystals.

Refinement top

Carbon-bound hydrogen atoms were placed at calculated positions (C–H 0.95–0.99 Å) and were treated as riding on their parent atoms, with U(H) set to 1.2 times Ueq(C). The water H-atoms were located in a difference Fourier map, and were refined with a distance restraint of O–H 0.84±0.01 Å; their temperature factors were freely refined. The amino H-atom could not be located, and was treated as riding.

The structure is a racemic twin. The explicit refinement of the Flack parameter gave the twin component as 0.38 (2).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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: pubCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of Co(C12H8N2)(C4H5NO4)(H2O).H2O at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
Aqua(iminodiacetato-κ3O,N,O')(1,10- phenanthroline-κ2N,N')cobalt(II) monohydrate top
Crystal data top
[Co(C4H5NO4)(C12H8N2)(H2O)]·H2OF(000) = 418
Mr = 406.26Dx = 1.650 Mg m−3
Monoclinic, PnMo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yacCell parameters from 1265 reflections
a = 6.7884 (3) Åθ = 2.6–24.5°
b = 12.0903 (5) ŵ = 1.09 mm−1
c = 10.4945 (4) ÅT = 100 K
β = 108.357 (3)°Prism, orange
V = 817.49 (6) Å30.35 × 0.02 × 0.02 mm
Z = 2
Data collection top
Bruker SMART APEX
diffractometer		3639 independent reflections
Radiation source: fine-focus sealed tube2997 reflections with I > 2σ(I)
graphiteRint = 0.048
ω scansθmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −8→8
Tmin = 0.701, Tmax = 0.979k = −15→15
6417 measured reflectionsl = −13→13
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.126 w = 1/[σ2(Fo2) + (0.0697P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
3639 reflectionsΔρmax = 0.86 e Å−3
248 parametersΔρmin = −0.49 e Å−3
8 restraintsAbsolute structure: Flack (1983), 1746 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.38 (2)
Crystal data top
[Co(C4H5NO4)(C12H8N2)(H2O)]·H2OV = 817.49 (6) Å3
Mr = 406.26Z = 2
Monoclinic, PnMo Kα radiation
a = 6.7884 (3) ŵ = 1.09 mm−1
b = 12.0903 (5) ÅT = 100 K
c = 10.4945 (4) Å0.35 × 0.02 × 0.02 mm
β = 108.357 (3)°
Data collection top
Bruker SMART APEX
diffractometer		3639 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2997 reflections with I > 2σ(I)
Tmin = 0.701, Tmax = 0.979Rint = 0.048
6417 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.048H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.126Δρmax = 0.86 e Å−3
S = 1.00Δρmin = −0.49 e Å−3
3639 reflectionsAbsolute structure: Flack (1983), 1746 Friedel pairs
248 parametersFlack parameter: 0.38 (2)
8 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Co10.49999 (10)0.85733 (5)0.50000 (8)0.01527 (16)
O10.4183 (7)0.8730 (3)0.6730 (4)0.0222 (9)
O20.3360 (6)1.0019 (3)0.7965 (4)0.0254 (8)
O30.7258 (6)0.9787 (3)0.5790 (3)0.0196 (9)
O40.7806 (5)1.1607 (3)0.5786 (3)0.0190 (7)
O1W0.5702 (6)0.8446 (3)0.3211 (4)0.0194 (9)
H110.652 (7)0.896 (3)0.317 (5)0.029*
H120.493 (7)0.830 (4)0.243 (2)0.029*
O2W0.9365 (7)1.2706 (3)0.3875 (4)0.0307 (9)
H210.939 (10)1.225 (4)0.327 (4)0.046*
H220.870 (9)1.243 (4)0.435 (5)0.046*
N10.3129 (7)1.0058 (4)0.4480 (4)0.0162 (10)
H10.21040.99680.37270.019*
N20.6902 (8)0.7165 (4)0.5733 (5)0.0171 (10)
N30.2824 (7)0.7278 (4)0.4343 (4)0.0168 (11)
C10.3389 (7)0.9654 (4)0.6867 (5)0.0193 (10)
C20.2335 (7)1.0313 (4)0.5604 (5)0.0202 (10)
H2A0.08261.01600.53200.024*
H2B0.25331.11120.58140.024*
C30.4607 (8)1.0907 (4)0.4324 (5)0.0183 (10)
H3A0.40621.16530.44140.022*
H3B0.47601.08490.34190.022*
C40.6704 (8)1.0754 (4)0.5382 (5)0.0177 (10)
C50.8890 (9)0.7128 (5)0.6410 (5)0.0217 (13)
H50.96250.78060.66380.026*
C60.9974 (10)0.6143 (5)0.6811 (6)0.0256 (13)
H61.14100.61540.73100.031*
C70.8948 (9)0.5164 (5)0.6478 (5)0.0246 (13)
H70.96660.44850.67360.030*
C80.6812 (10)0.5167 (5)0.5748 (5)0.0221 (13)
C90.5835 (10)0.6199 (5)0.5401 (7)0.0210 (14)
C100.5597 (10)0.4182 (5)0.5380 (6)0.0269 (14)
H100.62470.34810.56010.032*
C110.3534 (10)0.4234 (4)0.4720 (6)0.0230 (12)
H11A0.27540.35700.45000.028*
C120.2518 (10)0.5267 (5)0.4351 (5)0.0205 (13)
C130.3668 (10)0.6250 (4)0.4676 (6)0.0128 (12)
C140.0390 (9)0.5374 (4)0.3682 (5)0.0220 (12)
H14−0.04620.47340.34590.026*
C15−0.0462 (10)0.6399 (4)0.3350 (6)0.0238 (14)
H15−0.19020.64750.28840.029*
C160.0795 (8)0.7328 (5)0.3699 (6)0.0182 (11)
H160.01750.80350.34670.022*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Co10.0158 (3)0.0120 (3)0.0173 (3)0.0003 (3)0.0041 (2)−0.0001 (3)
O10.033 (3)0.0132 (18)0.024 (2)0.0052 (16)0.0135 (19)0.0029 (14)
O20.0220 (19)0.032 (2)0.0207 (17)0.0070 (16)0.0052 (14)−0.0024 (16)
O30.017 (2)0.0178 (19)0.021 (2)0.0012 (15)0.0013 (16)0.0033 (15)
O40.0219 (18)0.0127 (17)0.0210 (17)−0.0021 (14)0.0048 (14)0.0012 (13)
O1W0.014 (2)0.023 (2)0.0183 (19)−0.0049 (15)0.0022 (16)0.0039 (15)
O2W0.049 (3)0.0175 (19)0.029 (2)−0.0081 (18)0.0165 (19)−0.0030 (15)
N10.010 (2)0.022 (3)0.012 (2)−0.0009 (18)−0.0025 (17)0.0020 (19)
N20.019 (2)0.011 (2)0.022 (2)0.0010 (19)0.0077 (19)−0.0011 (19)
N30.021 (2)0.015 (2)0.014 (2)0.0008 (19)0.0053 (19)−0.0012 (18)
C10.012 (2)0.027 (3)0.017 (2)0.001 (2)0.0017 (19)−0.001 (2)
C20.015 (2)0.021 (2)0.025 (3)0.0072 (19)0.008 (2)0.003 (2)
C30.017 (3)0.013 (2)0.022 (2)−0.002 (2)0.002 (2)0.0032 (19)
C40.020 (3)0.016 (3)0.017 (2)0.001 (2)0.007 (2)0.001 (2)
C50.019 (3)0.026 (3)0.018 (3)0.002 (2)0.003 (2)−0.004 (2)
C60.017 (3)0.034 (3)0.022 (3)0.008 (3)0.002 (2)0.004 (2)
C70.027 (3)0.021 (3)0.026 (3)0.012 (2)0.008 (2)0.008 (2)
C80.027 (3)0.020 (3)0.023 (3)0.004 (2)0.013 (2)0.007 (2)
C90.023 (3)0.018 (3)0.024 (3)0.001 (2)0.009 (2)0.000 (2)
C100.041 (4)0.011 (2)0.033 (3)0.004 (2)0.017 (3)0.002 (2)
C110.029 (3)0.013 (2)0.030 (3)−0.001 (2)0.014 (2)0.001 (2)
C120.029 (3)0.015 (3)0.022 (3)−0.004 (2)0.013 (3)0.000 (2)
C130.016 (3)0.010 (3)0.013 (2)0.003 (2)0.006 (2)0.0001 (19)
C140.019 (3)0.019 (3)0.027 (3)−0.007 (2)0.006 (2)−0.002 (2)
C150.019 (3)0.025 (3)0.027 (3)−0.005 (2)0.006 (2)−0.003 (2)
C160.012 (2)0.016 (3)0.023 (3)0.003 (2)0.001 (2)−0.003 (2)
Geometric parameters (Å, °) top
Co1—O12.067 (4)C3—C41.516 (7)
Co1—O1W2.083 (4)C3—H3A0.9900
Co1—O32.095 (4)C3—H3B0.9900
Co1—N32.113 (5)C5—C61.394 (8)
Co1—N22.129 (5)C5—H50.9500
Co1—N12.167 (5)C6—C71.362 (8)
O1—C11.269 (6)C6—H60.9500
O2—C11.240 (6)C7—C81.411 (8)
O3—C41.260 (6)C7—H70.9500
O4—C41.267 (6)C8—C91.406 (9)
O1W—H110.84 (5)C8—C101.430 (8)
O1W—H120.84 (6)C9—C131.429 (8)
O2W—H210.84 (5)C10—C111.355 (9)
O2W—H220.84 (6)C10—H100.9500
N1—C21.476 (6)C11—C121.420 (8)
N1—C31.480 (6)C11—H11A0.9500
N1—H10.8800C12—C141.399 (9)
N2—C51.313 (8)C12—C131.403 (8)
N2—C91.360 (8)C14—C151.365 (8)
N3—C161.331 (7)C14—H140.9500
N3—C131.368 (7)C15—C161.389 (8)
C1—C21.518 (6)C15—H150.9500
C2—H2A0.9900C16—H160.9500
C2—H2B0.9900
O1—Co1—O1W177.6 (2)C4—C3—H3A109.6
O1—Co1—O387.34 (16)N1—C3—H3B109.6
O1W—Co1—O393.54 (15)C4—C3—H3B109.6
O1—Co1—N390.07 (17)H3A—C3—H3B108.1
O1W—Co1—N389.20 (16)O3—C4—O4124.0 (5)
O3—Co1—N3175.53 (17)O3—C4—C3118.3 (5)
O1—Co1—N293.20 (16)O4—C4—C3117.7 (4)
O1W—Co1—N288.95 (17)N2—C5—C6123.2 (6)
O3—Co1—N297.62 (17)N2—C5—H5118.4
N3—Co1—N278.88 (15)C6—C5—H5118.4
O1—Co1—N181.23 (15)C7—C6—C5119.1 (6)
O1W—Co1—N196.68 (15)C7—C6—H6120.4
O3—Co1—N179.47 (17)C5—C6—H6120.4
N3—Co1—N1103.74 (19)C6—C7—C8119.5 (5)
N2—Co1—N1173.79 (18)C6—C7—H7120.2
C1—O1—Co1114.9 (3)C8—C7—H7120.2
C4—O3—Co1114.3 (3)C9—C8—C7117.5 (5)
Co1—O1W—H11109 (3)C9—C8—C10119.0 (5)
Co1—O1W—H12130 (3)C7—C8—C10123.5 (5)
H11—O1W—H12109 (5)N2—C9—C8121.7 (6)
H21—O2W—H22109 (5)N2—C9—C13118.4 (6)
C2—N1—C3111.9 (4)C8—C9—C13119.9 (6)
C2—N1—Co1107.7 (3)C11—C10—C8121.0 (5)
C3—N1—Co1103.8 (3)C11—C10—H10119.5
C2—N1—H1111.0C8—C10—H10119.5
C3—N1—H1111.0C10—C11—C12121.0 (6)
Co1—N1—H1111.0C10—C11—H11A119.5
C5—N2—C9118.9 (5)C12—C11—H11A119.5
C5—N2—Co1128.7 (4)C14—C12—C13116.9 (5)
C9—N2—Co1112.4 (4)C14—C12—C11123.6 (5)
C16—N3—C13117.0 (5)C13—C12—C11119.5 (6)
C16—N3—Co1129.6 (4)N3—C13—C12123.5 (6)
C13—N3—Co1113.4 (4)N3—C13—C9116.9 (6)
O2—C1—O1123.4 (5)C12—C13—C9119.6 (6)
O2—C1—C2118.9 (4)C15—C14—C12119.9 (5)
O1—C1—C2117.6 (4)C15—C14—H14120.0
N1—C2—C1113.4 (4)C12—C14—H14120.0
N1—C2—H2A108.9C14—C15—C16119.5 (6)
C1—C2—H2A108.9C14—C15—H15120.3
N1—C2—H2B108.9C16—C15—H15120.3
C1—C2—H2B108.9N3—C16—C15123.3 (5)
H2A—C2—H2B107.7N3—C16—H16118.4
N1—C3—C4110.3 (4)C15—C16—H16118.4
N1—C3—H3A109.6
O3—Co1—O1—C166.7 (4)Co1—O3—C4—C3−4.4 (6)
N3—Co1—O1—C1−116.9 (4)N1—C3—C4—O331.4 (6)
N2—Co1—O1—C1164.2 (4)N1—C3—C4—O4−149.6 (4)
N1—Co1—O1—C1−13.1 (4)C9—N2—C5—C6−0.1 (8)
O1—Co1—O3—C4−96.3 (4)Co1—N2—C5—C6−178.6 (4)
O1W—Co1—O3—C481.5 (4)N2—C5—C6—C70.8 (9)
N2—Co1—O3—C4170.9 (3)C5—C6—C7—C8−0.6 (8)
N1—Co1—O3—C4−14.7 (4)C6—C7—C8—C9−0.3 (8)
O1—Co1—N1—C2−1.0 (3)C6—C7—C8—C10−178.6 (5)
O1W—Co1—N1—C2177.7 (3)C5—N2—C9—C8−0.9 (8)
O3—Co1—N1—C2−89.9 (3)Co1—N2—C9—C8177.9 (4)
N3—Co1—N1—C286.9 (3)C5—N2—C9—C13179.4 (5)
O1—Co1—N1—C3117.8 (3)Co1—N2—C9—C13−1.9 (6)
O1W—Co1—N1—C3−63.4 (3)C7—C8—C9—N21.0 (8)
O3—Co1—N1—C328.9 (3)C10—C8—C9—N2179.4 (5)
N3—Co1—N1—C3−154.3 (3)C7—C8—C9—C13−179.2 (5)
O1—Co1—N2—C5−90.5 (5)C10—C8—C9—C13−0.8 (7)
O1W—Co1—N2—C590.7 (5)C9—C8—C10—C11−0.7 (8)
O3—Co1—N2—C5−2.8 (5)C7—C8—C10—C11177.6 (5)
N3—Co1—N2—C5−180.0 (5)C8—C10—C11—C121.1 (8)
O1—Co1—N2—C990.9 (4)C10—C11—C12—C14−179.3 (5)
O1W—Co1—N2—C9−88.0 (4)C10—C11—C12—C130.0 (8)
O3—Co1—N2—C9178.6 (4)C16—N3—C13—C121.3 (8)
N3—Co1—N2—C91.4 (4)Co1—N3—C13—C12179.6 (4)
O1—Co1—N3—C1684.0 (5)C16—N3—C13—C9−178.2 (5)
O1W—Co1—N3—C16−93.7 (5)Co1—N3—C13—C90.1 (6)
N2—Co1—N3—C16177.2 (5)C14—C12—C13—N3−1.7 (8)
N1—Co1—N3—C163.0 (5)C11—C12—C13—N3179.0 (5)
O1—Co1—N3—C13−94.1 (4)C14—C12—C13—C9177.8 (5)
O1W—Co1—N3—C1388.3 (4)C11—C12—C13—C9−1.5 (7)
N2—Co1—N3—C13−0.8 (4)N2—C9—C13—N31.2 (7)
N1—Co1—N3—C13−175.0 (3)C8—C9—C13—N3−178.5 (5)
Co1—O1—C1—O2−158.4 (4)N2—C9—C13—C12−178.3 (5)
Co1—O1—C1—C224.6 (6)C8—C9—C13—C121.9 (7)
C3—N1—C2—C1−101.0 (5)C13—C12—C14—C151.4 (8)
Co1—N1—C2—C112.5 (5)C11—C12—C14—C15−179.2 (5)
O2—C1—C2—N1157.4 (4)C12—C14—C15—C16−0.9 (9)
O1—C1—C2—N1−25.4 (6)C13—N3—C16—C15−0.7 (8)
C2—N1—C3—C477.1 (5)Co1—N3—C16—C15−178.7 (4)
Co1—N1—C3—C4−38.8 (4)C14—C15—C16—N30.5 (9)
Co1—O3—C4—O4176.7 (4)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1w—H11···O2i0.84 (5)1.82 (4)2.656 (5)174 (6)
O1w—H12···O4ii0.84 (6)1.87 (4)2.682 (5)162 (6)
O2w—H21···O1i0.84 (5)1.98 (4)2.815 (5)174 (7)
O2w—H22···O40.84 (6)2.05 (5)2.871 (5)165 (6)
N1—H1···O2ii0.882.413.126 (6)139
Symmetry codes: (i) x+1/2, −y+2, z−1/2; (ii) x−1/2, −y+2, z−1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1w—H11···O2i0.84 (5)1.82 (4)2.656 (5)174 (6)
O1w—H12···O4ii0.84 (6)1.87 (4)2.682 (5)162 (6)
O2w—H21···O1i0.84 (5)1.98 (4)2.815 (5)174 (7)
O2w—H22···O40.84 (6)2.05 (5)2.871 (5)165 (6)
Symmetry codes: (i) x+1/2, −y+2, z−1/2; (ii) x−1/2, −y+2, z−1/2.
Acknowledgements top

We thank Universiti Tunku Abdul Rahman and the University of Malaya for supporting this study.

references
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