metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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{6,6′-Di­meth­oxy-2,2′-[cyclo­hexane-1,2-diylbis(nitrilo­methyl­­idyne)]diphenolato-κ4O1,N,N′,O1′}iron(II) monohydrate

aSchool of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China
*Correspondence e-mail: gmli@hlju.edu.cn

(Received 23 May 2009; accepted 11 June 2009; online 27 June 2009)

In the title complex, [Fe(C22H24N2O4)]·H2O, the FeII center is four-coordinated by two O and two N atoms from 2,2′-[6,6′-dimethoxy­cyclo­hexane-1,2-diylbis(nitrilo­methyl­idyne)]diphen­olate (L) ligands in a distorted square-planar geometry. Uncoordinated water and FeL mol­ecules are paired via inter­molecular water–meth­oxy O—H⋯O hydrogen bonds.

Related literature

For a manganese complex of a similar Schiff base ligand, see: Watkinson et al. (1999[Watkinson, M., Fondo, M., Bermejo, M. R., Sousa, A., McAuliffe, C. A., Pritchard, R. G., Jaiboon, N., Aurangzeb, N. & Naeem, M. (1999). J. Chem. Soc. Dalton Trans. pp. 31-41.]). For the isotypic CoII compound, see: Bao et al. (2009[Bao, Y., Li, H.-F., Yan, P.-F. Li, G.-M. & Hou, G.-F. (2009). Acta Cryst. E65, m770.]).

[Scheme 1]

Experimental

Crystal data
  • [Fe(C22H24N2O4)]·H2O

  • Mr = 454.30

  • Monoclinic, P 21 /n

  • a = 11.243 (5) Å

  • b = 10.617 (3) Å

  • c = 17.863 (7) Å

  • β = 107.042 (14)°

  • V = 2038.5 (13) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.78 mm−1

  • T = 291 K

  • 0.22 × 0.21 × 0.18 mm

Data collection
  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.846, Tmax = 0.873

  • 18680 measured reflections

  • 4584 independent reflections

  • 3446 reflections with I > 2σ(I)

  • Rint = 0.054

Refinement
  • R[F2 > 2σ(F2)] = 0.042

  • wR(F2) = 0.107

  • S = 1.03

  • 4584 reflections

  • 273 parameters

  • H-atom parameters constrained

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.35 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O5—H2⋯O2 0.85 2.15 2.915 (4) 149
O5—H1⋯O4 0.85 2.06 2.898 (4) 169

Data collection: RAPID-AUTO (Rigaku, 1998[Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002[Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

In the title compound (Fig. 1), the FeII ion is four-coordinated by the tetradentate Schiff base ligand in a square planar environment in a manner observed earlier for a manganese complex (Watkinson et al., 1999). Uncoordinated water molecule is paired with the main molecule by the O—H···O hydrogen bonds (Table 1, Fig. 1).

Related literature top

For a manganese complex of a similar Schiff base ligand, see: Watkinson et al. (1999). For the isotypic CoII compound, see: Bao et al. (2009).

Experimental top

The title complex was obtained by the treatment of anhydrous ferrous chloride with the Schiff base in methanol/acetone (2:3). The yellow clear mixture turned to black precipitation immediately, stirred for 4 h; diethyl ether was allowed to diffuse slowly into the solution of the filtrate. Black single crystals were obtained after several days. Analysis calculated for C22H26FeN2O5: C, 58.16; H, 5.77; N, 6.17; Fe, 12.29; found: C, 57.56; H, 5.23; N, 6.77; F, 12.79%.

Refinement top

H atoms bound to C atoms were placed in calculated positions and treated as riding on their parent atoms, with C—H = 0.93 Å (aromatic C), C—H = 0.97 Å (methylene C), C—H = 0.98 Å (methine C), and with Uiso(H) = 1.2Ueq(C) or C—H = 0.96 Å (methly C) and with Uiso(H) = 1.5Ueq(C). Water H atoms were initially located in a difference Fourier map, but they were treated as riding on their parent atoms with O—H = 0.85 Å and with with Uiso(H) = 1.5Ueq(O).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. View of the title compound showing the atomic numbering and 30% probability displacement ellipsoids. Dashed lines indicate the hydrogen-bonding interactions.
{6,6'-Dimethoxy-2,2'-[cyclohexane-1,2-diylbis(nitrilomethylidyne)]diphenolato- κ4O1,N,N',O1'}iron(II) monohydrate top
Crystal data top
[Fe(C22H24N2O4)]·H2OF(000) = 952
Mr = 454.30Dx = 1.480 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 13436 reflections
a = 11.243 (5) Åθ = 3.1–27.5°
b = 10.617 (3) ŵ = 0.78 mm1
c = 17.863 (7) ÅT = 291 K
β = 107.042 (14)°Block, black
V = 2038.5 (13) Å30.22 × 0.21 × 0.18 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer
4584 independent reflections
Radiation source: fine-focus sealed tube3446 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.054
ω scansθmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
h = 1414
Tmin = 0.846, Tmax = 0.873k = 1313
18680 measured reflectionsl = 2323
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0436P)2 + 1.092P]
where P = (Fo2 + 2Fc2)/3
4584 reflections(Δ/σ)max = 0.001
273 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.35 e Å3
Crystal data top
[Fe(C22H24N2O4)]·H2OV = 2038.5 (13) Å3
Mr = 454.30Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.243 (5) ŵ = 0.78 mm1
b = 10.617 (3) ÅT = 291 K
c = 17.863 (7) Å0.22 × 0.21 × 0.18 mm
β = 107.042 (14)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer
4584 independent reflections
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
3446 reflections with I > 2σ(I)
Tmin = 0.846, Tmax = 0.873Rint = 0.054
18680 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0420 restraints
wR(F2) = 0.107H-atom parameters constrained
S = 1.03Δρmax = 0.30 e Å3
4584 reflectionsΔρmin = 0.35 e Å3
273 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
xyzUiso*/Ueq
Fe10.65626 (3)0.46981 (3)0.162776 (18)0.02766 (11)
N10.7304 (2)0.52432 (19)0.08782 (12)0.0356 (5)
O10.55829 (18)0.34802 (16)0.09933 (10)0.0414 (4)
O30.57113 (19)0.43064 (17)0.23484 (11)0.0447 (5)
N20.7650 (2)0.5782 (2)0.23003 (12)0.0397 (5)
C70.6991 (3)0.4904 (2)0.01541 (15)0.0385 (6)
H70.73390.53500.01780.046*
C10.5517 (2)0.3230 (2)0.02601 (15)0.0370 (6)
C20.4762 (3)0.2205 (3)0.01171 (17)0.0439 (6)
C200.5684 (3)0.5024 (2)0.29420 (15)0.0401 (6)
O40.3917 (2)0.3866 (2)0.29798 (13)0.0597 (6)
C190.4729 (3)0.4826 (3)0.33048 (17)0.0481 (7)
O20.4206 (2)0.1564 (2)0.03582 (13)0.0636 (6)
C80.8176 (3)0.6325 (2)0.11520 (15)0.0394 (6)
H80.76760.70970.10750.047*
C140.7552 (3)0.6262 (2)0.29455 (15)0.0414 (6)
H140.81690.68140.32200.050*
C60.6156 (2)0.3903 (2)0.01837 (15)0.0372 (6)
C40.5227 (3)0.2627 (3)0.13222 (17)0.0517 (7)
H40.51170.24390.18470.062*
C150.6547 (3)0.5989 (3)0.32603 (15)0.0421 (6)
C50.5980 (3)0.3603 (3)0.09773 (16)0.0464 (7)
H50.63810.40750.12690.056*
C130.8726 (3)0.6129 (2)0.20281 (16)0.0411 (6)
H130.90910.69180.22770.049*
C120.9700 (3)0.5089 (3)0.22201 (18)0.0502 (7)
H12A0.93060.42870.20400.060*
H12B1.00670.50380.27830.060*
C30.4622 (3)0.1911 (3)0.08882 (17)0.0495 (7)
H30.41250.12340.11210.059*
C90.9182 (3)0.6509 (3)0.07480 (17)0.0486 (7)
H9A0.87980.65200.01860.058*
H9B0.95780.73190.08990.058*
C101.0165 (3)0.5485 (3)0.09490 (19)0.0594 (8)
H10A1.08220.56900.07190.071*
H10B0.97970.46920.07270.071*
C111.0719 (3)0.5339 (4)0.1833 (2)0.0648 (9)
H11A1.13070.46460.19430.078*
H11B1.11650.61010.20490.078*
C180.4656 (3)0.5554 (3)0.3928 (2)0.0633 (9)
H180.40180.54120.41520.076*
C210.2942 (3)0.3601 (4)0.3316 (2)0.0694 (10)
H21A0.32910.33030.38430.104*
H21B0.24050.29670.30120.104*
H21C0.24720.43540.33220.104*
C170.5525 (4)0.6499 (3)0.4229 (2)0.0674 (10)
H170.54680.69820.46510.081*
C160.6452 (3)0.6712 (3)0.39035 (18)0.0551 (8)
H160.70320.73420.41060.066*
O50.3096 (3)0.3010 (3)0.13694 (18)0.1061 (11)
H10.34240.32990.18270.159*
H20.36490.25940.12380.159*
C220.3307 (3)0.0621 (3)0.0015 (2)0.0666 (10)
H22A0.26090.10040.03600.100*
H22B0.30320.02190.04160.100*
H22C0.36740.00050.02430.100*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.02801 (19)0.03099 (18)0.02628 (18)0.00228 (14)0.01153 (13)0.00086 (13)
N10.0334 (12)0.0387 (11)0.0353 (11)0.0007 (9)0.0108 (9)0.0018 (9)
O10.0425 (11)0.0466 (10)0.0377 (10)0.0046 (8)0.0157 (8)0.0025 (7)
O30.0515 (12)0.0491 (10)0.0391 (10)0.0053 (9)0.0221 (9)0.0030 (8)
N20.0406 (13)0.0432 (12)0.0382 (12)0.0011 (10)0.0163 (10)0.0013 (9)
C70.0384 (15)0.0438 (14)0.0351 (14)0.0024 (11)0.0136 (12)0.0046 (10)
C10.0351 (15)0.0369 (13)0.0386 (14)0.0047 (10)0.0101 (12)0.0025 (10)
C20.0398 (16)0.0464 (15)0.0470 (16)0.0015 (12)0.0148 (13)0.0043 (12)
C200.0409 (16)0.0498 (15)0.0318 (13)0.0055 (11)0.0141 (12)0.0041 (10)
O40.0513 (14)0.0833 (15)0.0531 (13)0.0119 (11)0.0289 (11)0.0000 (11)
C190.0444 (18)0.0620 (18)0.0408 (16)0.0010 (14)0.0169 (13)0.0047 (13)
O20.0712 (16)0.0618 (13)0.0629 (14)0.0281 (11)0.0277 (12)0.0130 (10)
C80.0363 (15)0.0393 (14)0.0432 (15)0.0015 (11)0.0129 (12)0.0038 (11)
C140.0414 (16)0.0463 (15)0.0359 (14)0.0002 (12)0.0101 (12)0.0035 (11)
C60.0342 (14)0.0418 (14)0.0349 (13)0.0054 (11)0.0086 (11)0.0004 (10)
C40.0539 (19)0.0608 (18)0.0390 (16)0.0104 (14)0.0112 (14)0.0096 (13)
C150.0470 (17)0.0469 (15)0.0340 (14)0.0011 (12)0.0143 (12)0.0002 (11)
C50.0456 (18)0.0559 (17)0.0383 (15)0.0046 (13)0.0134 (13)0.0003 (12)
C130.0387 (16)0.0445 (14)0.0417 (15)0.0055 (11)0.0143 (12)0.0025 (11)
C120.0397 (17)0.0653 (19)0.0439 (16)0.0075 (13)0.0098 (13)0.0074 (13)
C30.0473 (18)0.0480 (16)0.0498 (17)0.0019 (13)0.0086 (14)0.0111 (13)
C90.0451 (18)0.0587 (18)0.0440 (16)0.0118 (13)0.0162 (14)0.0028 (12)
C100.0436 (19)0.085 (2)0.056 (2)0.0016 (16)0.0244 (16)0.0000 (16)
C110.0369 (18)0.098 (3)0.061 (2)0.0095 (17)0.0161 (15)0.0101 (18)
C180.057 (2)0.093 (3)0.0510 (19)0.0029 (18)0.0322 (17)0.0024 (16)
C210.046 (2)0.106 (3)0.065 (2)0.0016 (19)0.0290 (17)0.0186 (19)
C170.077 (3)0.084 (2)0.051 (2)0.001 (2)0.0337 (19)0.0176 (17)
C160.062 (2)0.0628 (19)0.0436 (17)0.0018 (15)0.0206 (15)0.0097 (13)
O50.080 (2)0.167 (3)0.080 (2)0.021 (2)0.0366 (17)0.0236 (19)
C220.055 (2)0.0543 (19)0.085 (3)0.0180 (15)0.0124 (19)0.0009 (16)
Geometric parameters (Å, º) top
Fe1—N21.844 (2)C4—H40.9300
Fe1—O11.8541 (18)C15—C161.412 (4)
Fe1—O31.8623 (19)C5—H50.9300
Fe1—N11.864 (2)C13—C121.523 (4)
N1—C71.288 (3)C13—H130.9800
N1—C81.496 (3)C12—C111.525 (4)
O1—C11.317 (3)C12—H12A0.9700
O3—C201.313 (3)C12—H12B0.9700
N2—C141.294 (3)C3—H30.9300
N2—C131.476 (3)C9—C101.517 (4)
C7—C61.429 (4)C9—H9A0.9700
C7—H70.9300C9—H9B0.9700
C1—C61.410 (4)C10—C111.525 (5)
C1—C21.423 (4)C10—H10A0.9700
C2—O21.373 (3)C10—H10B0.9700
C2—C31.376 (4)C11—H11A0.9700
C20—C151.411 (4)C11—H11B0.9700
C20—C191.424 (4)C18—C171.394 (5)
O4—C191.378 (4)C18—H180.9300
O4—C211.425 (4)C21—H21A0.9600
C19—C181.377 (4)C21—H21B0.9600
O2—C221.428 (4)C21—H21C0.9600
C8—C131.519 (4)C17—C161.352 (5)
C8—C91.522 (4)C17—H170.9300
C8—H80.9800C16—H160.9300
C14—C151.431 (4)O5—H10.8500
C14—H140.9300O5—H20.8500
C6—C51.409 (4)C22—H22A0.9600
C4—C51.365 (4)C22—H22B0.9600
C4—C31.397 (4)C22—H22C0.9600
N2—Fe1—O1174.23 (9)C8—C13—C12112.4 (2)
N2—Fe1—O393.78 (9)N2—C13—H13109.8
O1—Fe1—O386.17 (8)C8—C13—H13109.8
N2—Fe1—N185.62 (10)C12—C13—H13109.8
O1—Fe1—N195.05 (9)C13—C12—C11111.0 (2)
O3—Fe1—N1173.78 (9)C13—C12—H12A109.4
C7—N1—C8120.2 (2)C11—C12—H12A109.4
C7—N1—Fe1125.91 (19)C13—C12—H12B109.4
C8—N1—Fe1113.05 (16)C11—C12—H12B109.4
C1—O1—Fe1126.75 (17)H12A—C12—H12B108.0
C20—O3—Fe1124.53 (17)C2—C3—C4120.0 (3)
C14—N2—C13119.1 (2)C2—C3—H3120.0
C14—N2—Fe1127.8 (2)C4—C3—H3120.0
C13—N2—Fe1113.07 (16)C10—C9—C8112.8 (2)
N1—C7—C6125.7 (2)C10—C9—H9A109.0
N1—C7—H7117.1C8—C9—H9A109.0
C6—C7—H7117.1C10—C9—H9B109.0
O1—C1—C6124.6 (2)C8—C9—H9B109.0
O1—C1—C2118.5 (2)H9A—C9—H9B107.8
C6—C1—C2116.9 (2)C9—C10—C11111.5 (3)
O2—C2—C3124.5 (3)C9—C10—H10A109.3
O2—C2—C1113.8 (2)C11—C10—H10A109.3
C3—C2—C1121.7 (3)C9—C10—H10B109.3
O3—C20—C15124.8 (3)C11—C10—H10B109.3
O3—C20—C19118.8 (3)H10A—C10—H10B108.0
C15—C20—C19116.4 (2)C12—C11—C10110.7 (3)
C19—O4—C21117.7 (3)C12—C11—H11A109.5
C18—C19—O4124.5 (3)C10—C11—H11A109.5
C18—C19—C20121.2 (3)C12—C11—H11B109.5
O4—C19—C20114.3 (2)C10—C11—H11B109.5
C2—O2—C22118.4 (3)H11A—C11—H11B108.1
N1—C8—C13105.1 (2)C19—C18—C17120.9 (3)
N1—C8—C9116.7 (2)C19—C18—H18119.6
C13—C8—C9111.8 (2)C17—C18—H18119.6
N1—C8—H8107.6O4—C21—H21A109.5
C13—C8—H8107.6O4—C21—H21B109.5
C9—C8—H8107.6H21A—C21—H21B109.5
N2—C14—C15123.6 (3)O4—C21—H21C109.5
N2—C14—H14118.2H21A—C21—H21C109.5
C15—C14—H14118.2H21B—C21—H21C109.5
C5—C6—C1120.4 (2)C16—C17—C18119.8 (3)
C5—C6—C7118.3 (2)C16—C17—H17120.1
C1—C6—C7121.3 (2)C18—C17—H17120.1
C5—C4—C3120.1 (3)C17—C16—C15120.7 (3)
C5—C4—H4120.0C17—C16—H16119.6
C3—C4—H4120.0C15—C16—H16119.6
C20—C15—C16121.0 (3)H1—O5—H2107.8
C20—C15—C14121.1 (2)O2—C22—H22A109.5
C16—C15—C14117.8 (3)O2—C22—H22B109.5
C4—C5—C6120.8 (3)H22A—C22—H22B109.5
C4—C5—H5119.6O2—C22—H22C109.5
C6—C5—H5119.6H22A—C22—H22C109.5
N2—C13—C8104.4 (2)H22B—C22—H22C109.5
N2—C13—C12110.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H2···O10.852.523.102 (4)126
O5—H2···O20.852.152.915 (4)149
O5—H1···O30.852.693.254 (4)125
O5—H1···O40.852.062.898 (4)169

Experimental details

Crystal data
Chemical formula[Fe(C22H24N2O4)]·H2O
Mr454.30
Crystal system, space groupMonoclinic, P21/n
Temperature (K)291
a, b, c (Å)11.243 (5), 10.617 (3), 17.863 (7)
β (°) 107.042 (14)
V3)2038.5 (13)
Z4
Radiation typeMo Kα
µ (mm1)0.78
Crystal size (mm)0.22 × 0.21 × 0.18
Data collection
DiffractometerRigaku R-AXIS RAPID
diffractometer
Absorption correctionMulti-scan
(ABSCOR; Higashi, 1995)
Tmin, Tmax0.846, 0.873
No. of measured, independent and
observed [I > 2σ(I)] reflections
18680, 4584, 3446
Rint0.054
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.107, 1.03
No. of reflections4584
No. of parameters273
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.30, 0.35

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H2···O20.852.152.915 (4)149.1
O5—H1···O40.852.062.898 (4)169.0
 

Acknowledgements

The authors gratefully acknowledge financial support from the National Natural Science Foundation of China (grant Nos. 20572018 and 20672032), Heilongjiang Province (grant Nos. 1055HZ001, ZJG0504 and JC200605) and Heilongjiang University.

References

First citationBao, Y., Li, H.-F., Yan, P.-F. Li, G.-M. & Hou, G.-F. (2009). Acta Cryst. E65, m770.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationHigashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationRigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationRigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWatkinson, M., Fondo, M., Bermejo, M. R., Sousa, A., McAuliffe, C. A., Pritchard, R. G., Jaiboon, N., Aurangzeb, N. & Naeem, M. (1999). J. Chem. Soc. Dalton Trans. pp. 31–41.  Web of Science CSD CrossRef Google Scholar

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