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Acta Cryst. (2007). E63, m1631    [ doi:10.1107/S1600536807021824 ]

Triaqua[2-(carboxylatomethyliminomethyl)-4-formylphenolato-[kappa]3O,N,O']manganese(II) monohydrate

J.-H. Cai

Abstract top

The Mn atom in the title compound, [Mn(C10H7NO4)(H2O)3]·H2O, adopts an octahedral geometry owing to N,O,O'-tridentate chelation by the planar dianionic ligand. Intermolecular hydrogen bonds form a three-dimensional framework.

Comment top

Several crystal structures of metal complexes of salicylaldehyde–amino acids have reported (Wang et al.,1999; Reddy et al., 2004). The present study follows studies on the complexes of the Schiff bases derived from 5-formylsalicylaldehyde derivative (Liu et al., 2006; Cai et al., 2006a 2006b).

The title manganese complex (I) is chelated by the 5-formysalicylideneglycinate anion; it is also coordinated by three water molecules. The mononuclear molecule interacts with the lattice water molecule through hydrongen bonds (Table 1) to give rise to a three-dimensional, hydrogen-bonded network.

Related literature top

For metal complexes of Schiff bases derived from 5-formylsalicylaldehyde, see: Zeng et al. (2003); Liu et al. (2006); Cai et al. (2006a,b).

For related literature, see: Reddy et al. (2004); Wang et al. (1999).

Experimental top

5-Formylsalicylaldehyde (0.2 mmol, 0.268 g), glycine (0.2 mmol, 0.15 g) and potassium hydroxide (0.2 mmol, 0.112 g) were dissolved in aqueous methanol (80% 15 ml) to give a clear yellow solution. To the solution was added an aqueous solution (10 ml) of nanganese sulfate heptahydrate (1 mmol, 0.28 g). The mixture was heated at 323 K for 2 h. Brown crystals separated from the solution after several days.

Refinement top

Water H atoms were located in a difference Fourier map and refined with O–H distance restraints of 0.85 (1) Å, and with Uiso(H) = 1.5Ueq(O). Other H atoms were placed in calculated positions, with C—H = 0.93–0.97 Å, and refined in the riding-model approximation with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The structure of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme.
[Figure 2] Fig. 2. Packing of (I). Hydrogen bonds are shown as dotted lines.
Triaqua[2-(carboxylatomethyliminomethyl)-4-formylphenolato- κ3O,N,O']manganese(II) monohydrate top
Crystal data top
[Mn(C10H7NO4)(H2O)3]·H2OF(000) = 1368
Mr = 332.17Dx = 1.599 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 887 reflections
a = 11.208 (5) Åθ = 3.2–25.8°
b = 7.890 (3) ŵ = 0.99 mm−1
c = 31.212 (13) ÅT = 293 K
V = 2760 (2) Å3Layer, brown
Z = 80.20 × 0.15 × 0.05 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		3016 independent reflections
Radiation source: fine-focus sealed tube2197 reflections with I > 2σ(I)
graphiteRint = 0.050
φ and ω scansθmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 1998)		h = −5→14
Tmin = 0.836, Tmax = 0.952k = −9→10
12431 measured reflectionsl = −39→38
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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0509P)2 + 0.4197P]
where P = (Fo2 + 2Fc2)/3
2999 reflections(Δ/σ)max = 0.001
205 parametersΔρmax = 0.34 e Å−3
12 restraintsΔρmin = −0.52 e Å−3
Crystal data top
[Mn(C10H7NO4)(H2O)3]·H2OV = 2760 (2) Å3
Mr = 332.17Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 11.208 (5) ŵ = 0.99 mm−1
b = 7.890 (3) ÅT = 293 K
c = 31.212 (13) Å0.20 × 0.15 × 0.05 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		3016 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1998)		2197 reflections with I > 2σ(I)
Tmin = 0.836, Tmax = 0.952Rint = 0.050
12431 measured reflectionsθmax = 27.0°
Refinement top
R[F2 > 2σ(F2)] = 0.039H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.100Δρmax = 0.34 e Å−3
S = 1.04Δρmin = −0.52 e Å−3
2999 reflectionsAbsolute structure: ?
205 parametersFlack parameter: ?
12 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Mn10.43496 (3)0.08299 (5)0.321939 (11)0.02955 (13)
N10.58315 (17)0.0511 (3)0.36816 (6)0.0309 (5)
O10.36278 (15)0.2373 (2)0.37017 (5)0.0396 (4)
O20.3893 (2)0.4050 (3)0.56880 (7)0.0679 (7)
O30.56775 (15)−0.0691 (2)0.28804 (5)0.0370 (4)
O40.74624 (15)−0.1884 (3)0.28876 (5)0.0437 (5)
O50.35268 (18)−0.1504 (3)0.34151 (8)0.0572 (6)
O60.2977 (2)0.0909 (3)0.27446 (6)0.0543 (6)
O70.50884 (16)0.3129 (2)0.29047 (5)0.0393 (4)
O80.5092 (2)0.5967 (3)0.34947 (7)0.0630 (6)
C10.5816 (2)0.0875 (3)0.40768 (8)0.0343 (6)
H10.64560.04930.42400.041*
C20.4904 (2)0.1827 (3)0.43006 (7)0.0339 (6)
C30.5064 (2)0.2088 (4)0.47405 (8)0.0412 (6)
H30.57260.16040.48720.049*
C40.4289 (2)0.3029 (4)0.49883 (8)0.0419 (7)
C50.3320 (3)0.3787 (4)0.47888 (8)0.0458 (7)
H50.28020.44560.49490.055*
C60.3115 (2)0.3566 (4)0.43600 (9)0.0447 (7)
H60.24580.40890.42350.054*
C70.3878 (2)0.2563 (3)0.41017 (8)0.0334 (6)
C80.4519 (3)0.3259 (4)0.54424 (9)0.0512 (8)
H80.52030.27580.55540.061*
C90.6851 (2)−0.0454 (3)0.35156 (8)0.0365 (6)
H9A0.6995−0.14230.37000.044*
H9B0.75570.02560.35220.044*
C100.6639 (2)−0.1067 (3)0.30606 (8)0.0322 (5)
H5A0.3944 (18)−0.240 (2)0.3436 (9)0.048*
H5B0.2833 (11)−0.177 (3)0.3495 (9)0.048*
H6A0.287 (2)0.161 (2)0.2543 (6)0.048*
H6B0.268 (2)−0.0012 (18)0.2664 (7)0.048*
H7A0.4847 (19)0.338 (4)0.2659 (5)0.048*
H7B0.5840 (9)0.303 (4)0.2890 (8)0.048*
H8A0.498 (3)0.505 (2)0.3363 (7)0.048*
H8B0.527 (3)0.573 (3)0.3750 (4)0.048*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Mn10.0266 (2)0.0350 (2)0.0270 (2)0.00148 (16)−0.00204 (15)−0.00171 (16)
N10.0250 (10)0.0373 (12)0.0304 (11)0.0034 (9)−0.0014 (8)−0.0044 (9)
O10.0365 (10)0.0508 (11)0.0316 (9)0.0126 (9)−0.0046 (7)−0.0073 (8)
O20.0706 (15)0.0929 (18)0.0402 (12)0.0036 (13)0.0077 (11)−0.0221 (12)
O30.0323 (9)0.0491 (11)0.0297 (9)0.0066 (8)−0.0034 (7)−0.0042 (8)
O40.0293 (9)0.0582 (13)0.0436 (10)0.0083 (9)0.0021 (8)−0.0170 (9)
O50.0363 (11)0.0437 (12)0.0916 (16)−0.0060 (10)0.0136 (12)0.0115 (11)
O60.0614 (14)0.0505 (13)0.0509 (12)−0.0136 (11)−0.0297 (10)0.0098 (10)
O70.0332 (10)0.0478 (12)0.0368 (10)−0.0038 (9)−0.0013 (8)0.0088 (9)
O80.0815 (17)0.0497 (13)0.0577 (14)0.0077 (12)−0.0120 (13)−0.0068 (11)
C10.0308 (13)0.0387 (14)0.0334 (13)0.0039 (11)−0.0066 (10)−0.0031 (11)
C20.0339 (13)0.0374 (14)0.0303 (13)0.0016 (11)0.0000 (11)−0.0047 (11)
C30.0436 (15)0.0496 (17)0.0305 (13)0.0065 (14)−0.0049 (11)−0.0021 (12)
C40.0445 (15)0.0485 (17)0.0327 (14)−0.0023 (13)0.0037 (12)−0.0056 (12)
C50.0405 (15)0.0565 (18)0.0403 (15)0.0018 (14)0.0094 (12)−0.0130 (13)
C60.0351 (14)0.0521 (17)0.0468 (16)0.0111 (13)0.0011 (12)−0.0100 (13)
C70.0323 (13)0.0350 (14)0.0328 (13)−0.0020 (11)0.0014 (10)−0.0026 (11)
C80.0561 (18)0.064 (2)0.0334 (15)−0.0015 (16)0.0039 (13)−0.0096 (14)
C90.0294 (13)0.0443 (15)0.0357 (13)0.0062 (12)−0.0038 (11)−0.0061 (11)
C100.0306 (13)0.0311 (13)0.0347 (13)−0.0055 (11)0.0036 (10)−0.0028 (10)
Geometric parameters (Å, °) top
Mn1—O12.0982 (18)O8—H8A0.843 (10)
Mn1—O62.1367 (19)O8—H8B0.844 (10)
Mn1—O52.148 (2)C1—C21.448 (3)
Mn1—O32.1851 (18)C1—H10.9300
Mn1—N12.215 (2)C2—C31.400 (3)
Mn1—O72.2227 (19)C2—C71.431 (4)
N1—C11.267 (3)C3—C41.380 (4)
N1—C91.467 (3)C3—H30.9300
O1—C71.288 (3)C4—C51.387 (4)
O2—C81.213 (4)C4—C81.452 (4)
O3—C101.252 (3)C5—C61.369 (4)
O4—C101.249 (3)C5—H50.9300
O5—H5A0.847 (10)C6—C71.417 (4)
O5—H5B0.843 (10)C6—H60.9300
O6—H6A0.847 (9)C8—H80.9300
O6—H6B0.840 (9)C9—C101.519 (3)
O7—H7A0.836 (9)C9—H9A0.9700
O7—H7B0.848 (10)C9—H9B0.9700
O1—Mn1—O6101.72 (9)C2—C1—H1116.7
O1—Mn1—O597.34 (9)C3—C2—C7118.0 (2)
O6—Mn1—O585.02 (9)C3—C2—C1117.3 (2)
O1—Mn1—O3158.23 (6)C7—C2—C1124.7 (2)
O6—Mn1—O399.81 (8)C4—C3—C2123.2 (3)
O5—Mn1—O387.67 (8)C4—C3—H3118.4
O1—Mn1—N183.55 (7)C2—C3—H3118.4
O6—Mn1—N1174.32 (8)C3—C4—C5118.3 (2)
O5—Mn1—N192.25 (9)C3—C4—C8120.1 (3)
O3—Mn1—N175.06 (7)C5—C4—C8121.6 (3)
O1—Mn1—O789.27 (8)C6—C5—C4121.0 (3)
O6—Mn1—O786.44 (8)C6—C5—H5119.5
O5—Mn1—O7170.11 (8)C4—C5—H5119.5
O3—Mn1—O788.87 (7)C5—C6—C7121.8 (3)
N1—Mn1—O795.81 (7)C5—C6—H6119.1
C1—N1—C9118.2 (2)C7—C6—H6119.1
C1—N1—Mn1126.74 (17)O1—C7—C6119.0 (2)
C9—N1—Mn1114.38 (14)O1—C7—C2123.2 (2)
C7—O1—Mn1132.77 (16)C6—C7—C2117.7 (2)
C10—O3—Mn1119.94 (16)O2—C8—C4125.3 (3)
Mn1—O5—H5A119.8 (17)O2—C8—H8117.3
Mn1—O5—H5B133.8 (17)C4—C8—H8117.3
H5A—O5—H5B106.4 (15)N1—C9—C10111.97 (19)
Mn1—O6—H6A129.7 (17)N1—C9—H9A109.2
Mn1—O6—H6B118.2 (17)C10—C9—H9A109.2
H6A—O6—H6B106.6 (14)N1—C9—H9B109.2
Mn1—O7—H7A119 (2)C10—C9—H9B109.2
Mn1—O7—H7B108.5 (19)H9A—C9—H9B107.9
H7A—O7—H7B107.1 (15)O4—C10—O3124.4 (2)
H8A—O8—H8B107.6 (15)O4—C10—C9117.0 (2)
N1—C1—C2126.7 (2)O3—C10—C9118.6 (2)
N1—C1—H1116.7
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O7—H7A···O3i0.84 (1)1.93 (1)2.758 (3)172 (3)
O6—H6B···O4ii0.84 (1)2.28 (2)3.014 (3)146 (2)
O6—H6A···O4i0.85 (1)1.83 (1)2.677 (3)177 (3)
O5—H5B···O1iii0.84 (1)1.89 (1)2.723 (3)172 (2)
O8—H8B···O2iv0.84 (1)2.00 (1)2.793 (3)157 (3)
O5—H5A···O8v0.85 (1)1.83 (1)2.669 (3)169 (3)
O7—H7B···O4vi0.85 (1)1.90 (1)2.746 (3)172 (3)
O8—H8A···O70.84 (1)2.09 (1)2.900 (3)162 (3)
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x−1/2, y, −z+1/2; (iii) −x+1/2, y−1/2, z; (iv) −x+1, −y+1, −z+1; (v) x, y−1, z; (vi) −x+3/2, y+1/2, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O7—H7A···O3i0.84 (1)1.93 (1)2.758 (3)172 (3)
O6—H6B···O4ii0.84 (1)2.28 (2)3.014 (3)146 (2)
O6—H6A···O4i0.85 (1)1.83 (1)2.677 (3)177 (3)
O5—H5B···O1iii0.84 (1)1.89 (1)2.723 (3)172 (2)
O8—H8B···O2iv0.84 (1)2.00 (1)2.793 (3)157 (3)
O5—H5A···O8v0.85 (1)1.83 (1)2.669 (3)169 (3)
O7—H7B···O4vi0.85 (1)1.90 (1)2.746 (3)172 (3)
O8—H8A···O70.84 (1)2.09 (1)2.900 (3)162 (3)
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x−1/2, y, −z+1/2; (iii) −x+1/2, y−1/2, z; (iv) −x+1, −y+1, −z+1; (v) x, y−1, z; (vi) −x+3/2, y+1/2, z.
Acknowledgements top

This work was supported by the Ministry of Education Foundation of the Guangxi Chuang Autonomous Region of the People's Republic of China. We also thank Hechi University.

references
References top

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