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Acta Crystallogr Sect E Struct Rep Online. 2009 January 1; 65(Pt 1): m41.
Published online 2008 December 10. doi:  10.1107/S1600536808041226
PMCID: PMC2967887

Aqua­(imino­diacetato-κ3 O,N,O′)(1,10-phenanthroline-κ2 N,N′)cobalt(II) monohydrate

Abstract

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

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

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Object name is e-65-00m41-scheme1.jpg

Experimental

Crystal data

  • [Co(C4H5NO4)(C12H8N2)(H2O)]·H2O
  • M r = 406.26
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-00m41-efi1.jpg
  • a = 6.7884 (3) Å
  • b = 12.0903 (5) Å
  • c = 10.4945 (4) Å
  • β = 108.357 (3)°
  • V = 817.49 (6) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.09 mm−1
  • T = 100 (2) K
  • 0.35 × 0.02 × 0.02 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.701, T max = 0.979
  • 6417 measured reflections
  • 3639 independent reflections
  • 2997 reflections with I > 2σ(I)
  • R int = 0.048

Refinement

  • R[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.126
  • S = 1.00
  • 3639 reflections
  • 248 parameters
  • 8 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.86 e Å−3
  • Δρmin = −0.49 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1746 Friedel pairs
  • Flack parameter: 0.38 (2)

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808041226/sj2563sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808041226/sj2563Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Experimental

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

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).

Figures

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.

Crystal data

[Co(C4H5NO4)(C12H8N2)(H2O)]·H2OF(000) = 418
Mr = 406.26Dx = 1.650 Mg m3
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 mm1
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

Bruker SMART APEX diffractometer3639 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

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) = 0.126w = 1/[σ2(Fo2) + (0.0697P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
3639 reflectionsΔρmax = 0.86 e Å3
248 parametersΔρmin = −0.49 e Å3
8 restraintsAbsolute structure: Flack (1983), 1746 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.38 (2)

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

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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2563).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Su, J.-R. & Xu, D.-J. (2004). J. Coord. Chem.57, 223–229.
  • Westrip, S. P. (2009). publCIF In preparation.
  • Xu, D.-J., Cheng, C. R., Xu, Y.-Z. & Hu, S.-Z. (1989). Jiegou Huaxue, 8, 81–85.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography