Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807021824/ng2264sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807021824/ng2264Isup2.hkl |
CCDC reference: 650611
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.
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).
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.
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).
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.
Fig. 1. The structure of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme. | |
Fig. 2. Packing of (I). Hydrogen bonds are shown as dotted lines. |
[Mn(C10H7NO4)(H2O)3]·H2O | F(000) = 1368 |
Mr = 332.17 | Dx = 1.599 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 887 reflections |
a = 11.208 (5) Å | θ = 3.2–25.8° |
b = 7.890 (3) Å | µ = 0.99 mm−1 |
c = 31.212 (13) Å | T = 293 K |
V = 2760 (2) Å3 | Layer, brown |
Z = 8 | 0.20 × 0.15 × 0.05 mm |
Bruker SMART CCD area-detector diffractometer | 3016 independent reflections |
Radiation source: fine-focus sealed tube | 2197 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.050 |
φ and ω scans | θmax = 27.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | h = −5→14 |
Tmin = 0.836, Tmax = 0.952 | k = −9→10 |
12431 measured reflections | l = −39→38 |
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)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.100 | H 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 parameters | Δρmax = 0.34 e Å−3 |
12 restraints | Δρmin = −0.52 e Å−3 |
[Mn(C10H7NO4)(H2O)3]·H2O | V = 2760 (2) Å3 |
Mr = 332.17 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 11.208 (5) Å | µ = 0.99 mm−1 |
b = 7.890 (3) Å | T = 293 K |
c = 31.212 (13) Å | 0.20 × 0.15 × 0.05 mm |
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 = 0.952 | Rint = 0.050 |
12431 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 12 restraints |
wR(F2) = 0.100 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.34 e Å−3 |
2999 reflections | Δρmin = −0.52 e Å−3 |
205 parameters |
x | y | z | Uiso*/Ueq | ||
Mn1 | 0.43496 (3) | 0.08299 (5) | 0.321939 (11) | 0.02955 (13) | |
N1 | 0.58315 (17) | 0.0511 (3) | 0.36816 (6) | 0.0309 (5) | |
O1 | 0.36278 (15) | 0.2373 (2) | 0.37017 (5) | 0.0396 (4) | |
O2 | 0.3893 (2) | 0.4050 (3) | 0.56880 (7) | 0.0679 (7) | |
O3 | 0.56775 (15) | −0.0691 (2) | 0.28804 (5) | 0.0370 (4) | |
O4 | 0.74624 (15) | −0.1884 (3) | 0.28876 (5) | 0.0437 (5) | |
O5 | 0.35268 (18) | −0.1504 (3) | 0.34151 (8) | 0.0572 (6) | |
O6 | 0.2977 (2) | 0.0909 (3) | 0.27446 (6) | 0.0543 (6) | |
O7 | 0.50884 (16) | 0.3129 (2) | 0.29047 (5) | 0.0393 (4) | |
O8 | 0.5092 (2) | 0.5967 (3) | 0.34947 (7) | 0.0630 (6) | |
C1 | 0.5816 (2) | 0.0875 (3) | 0.40768 (8) | 0.0343 (6) | |
H1 | 0.6456 | 0.0493 | 0.4240 | 0.041* | |
C2 | 0.4904 (2) | 0.1827 (3) | 0.43006 (7) | 0.0339 (6) | |
C3 | 0.5064 (2) | 0.2088 (4) | 0.47405 (8) | 0.0412 (6) | |
H3 | 0.5726 | 0.1604 | 0.4872 | 0.049* | |
C4 | 0.4289 (2) | 0.3029 (4) | 0.49883 (8) | 0.0419 (7) | |
C5 | 0.3320 (3) | 0.3787 (4) | 0.47888 (8) | 0.0458 (7) | |
H5 | 0.2802 | 0.4456 | 0.4949 | 0.055* | |
C6 | 0.3115 (2) | 0.3566 (4) | 0.43600 (9) | 0.0447 (7) | |
H6 | 0.2458 | 0.4089 | 0.4235 | 0.054* | |
C7 | 0.3878 (2) | 0.2563 (3) | 0.41017 (8) | 0.0334 (6) | |
C8 | 0.4519 (3) | 0.3259 (4) | 0.54424 (9) | 0.0512 (8) | |
H8 | 0.5203 | 0.2758 | 0.5554 | 0.061* | |
C9 | 0.6851 (2) | −0.0454 (3) | 0.35156 (8) | 0.0365 (6) | |
H9A | 0.6995 | −0.1423 | 0.3700 | 0.044* | |
H9B | 0.7557 | 0.0256 | 0.3522 | 0.044* | |
C10 | 0.6639 (2) | −0.1067 (3) | 0.30606 (8) | 0.0322 (5) | |
H5A | 0.3944 (18) | −0.240 (2) | 0.3436 (9) | 0.048* | |
H5B | 0.2833 (11) | −0.177 (3) | 0.3495 (9) | 0.048* | |
H6A | 0.287 (2) | 0.161 (2) | 0.2543 (6) | 0.048* | |
H6B | 0.268 (2) | −0.0012 (18) | 0.2664 (7) | 0.048* | |
H7A | 0.4847 (19) | 0.338 (4) | 0.2659 (5) | 0.048* | |
H7B | 0.5840 (9) | 0.303 (4) | 0.2890 (8) | 0.048* | |
H8A | 0.498 (3) | 0.505 (2) | 0.3363 (7) | 0.048* | |
H8B | 0.527 (3) | 0.573 (3) | 0.3750 (4) | 0.048* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Mn1 | 0.0266 (2) | 0.0350 (2) | 0.0270 (2) | 0.00148 (16) | −0.00204 (15) | −0.00171 (16) |
N1 | 0.0250 (10) | 0.0373 (12) | 0.0304 (11) | 0.0034 (9) | −0.0014 (8) | −0.0044 (9) |
O1 | 0.0365 (10) | 0.0508 (11) | 0.0316 (9) | 0.0126 (9) | −0.0046 (7) | −0.0073 (8) |
O2 | 0.0706 (15) | 0.0929 (18) | 0.0402 (12) | 0.0036 (13) | 0.0077 (11) | −0.0221 (12) |
O3 | 0.0323 (9) | 0.0491 (11) | 0.0297 (9) | 0.0066 (8) | −0.0034 (7) | −0.0042 (8) |
O4 | 0.0293 (9) | 0.0582 (13) | 0.0436 (10) | 0.0083 (9) | 0.0021 (8) | −0.0170 (9) |
O5 | 0.0363 (11) | 0.0437 (12) | 0.0916 (16) | −0.0060 (10) | 0.0136 (12) | 0.0115 (11) |
O6 | 0.0614 (14) | 0.0505 (13) | 0.0509 (12) | −0.0136 (11) | −0.0297 (10) | 0.0098 (10) |
O7 | 0.0332 (10) | 0.0478 (12) | 0.0368 (10) | −0.0038 (9) | −0.0013 (8) | 0.0088 (9) |
O8 | 0.0815 (17) | 0.0497 (13) | 0.0577 (14) | 0.0077 (12) | −0.0120 (13) | −0.0068 (11) |
C1 | 0.0308 (13) | 0.0387 (14) | 0.0334 (13) | 0.0039 (11) | −0.0066 (10) | −0.0031 (11) |
C2 | 0.0339 (13) | 0.0374 (14) | 0.0303 (13) | 0.0016 (11) | 0.0000 (11) | −0.0047 (11) |
C3 | 0.0436 (15) | 0.0496 (17) | 0.0305 (13) | 0.0065 (14) | −0.0049 (11) | −0.0021 (12) |
C4 | 0.0445 (15) | 0.0485 (17) | 0.0327 (14) | −0.0023 (13) | 0.0037 (12) | −0.0056 (12) |
C5 | 0.0405 (15) | 0.0565 (18) | 0.0403 (15) | 0.0018 (14) | 0.0094 (12) | −0.0130 (13) |
C6 | 0.0351 (14) | 0.0521 (17) | 0.0468 (16) | 0.0111 (13) | 0.0011 (12) | −0.0100 (13) |
C7 | 0.0323 (13) | 0.0350 (14) | 0.0328 (13) | −0.0020 (11) | 0.0014 (10) | −0.0026 (11) |
C8 | 0.0561 (18) | 0.064 (2) | 0.0334 (15) | −0.0015 (16) | 0.0039 (13) | −0.0096 (14) |
C9 | 0.0294 (13) | 0.0443 (15) | 0.0357 (13) | 0.0062 (12) | −0.0038 (11) | −0.0061 (11) |
C10 | 0.0306 (13) | 0.0311 (13) | 0.0347 (13) | −0.0055 (11) | 0.0036 (10) | −0.0028 (10) |
Mn1—O1 | 2.0982 (18) | O8—H8A | 0.843 (10) |
Mn1—O6 | 2.1367 (19) | O8—H8B | 0.844 (10) |
Mn1—O5 | 2.148 (2) | C1—C2 | 1.448 (3) |
Mn1—O3 | 2.1851 (18) | C1—H1 | 0.9300 |
Mn1—N1 | 2.215 (2) | C2—C3 | 1.400 (3) |
Mn1—O7 | 2.2227 (19) | C2—C7 | 1.431 (4) |
N1—C1 | 1.267 (3) | C3—C4 | 1.380 (4) |
N1—C9 | 1.467 (3) | C3—H3 | 0.9300 |
O1—C7 | 1.288 (3) | C4—C5 | 1.387 (4) |
O2—C8 | 1.213 (4) | C4—C8 | 1.452 (4) |
O3—C10 | 1.252 (3) | C5—C6 | 1.369 (4) |
O4—C10 | 1.249 (3) | C5—H5 | 0.9300 |
O5—H5A | 0.847 (10) | C6—C7 | 1.417 (4) |
O5—H5B | 0.843 (10) | C6—H6 | 0.9300 |
O6—H6A | 0.847 (9) | C8—H8 | 0.9300 |
O6—H6B | 0.840 (9) | C9—C10 | 1.519 (3) |
O7—H7A | 0.836 (9) | C9—H9A | 0.9700 |
O7—H7B | 0.848 (10) | C9—H9B | 0.9700 |
O1—Mn1—O6 | 101.72 (9) | C2—C1—H1 | 116.7 |
O1—Mn1—O5 | 97.34 (9) | C3—C2—C7 | 118.0 (2) |
O6—Mn1—O5 | 85.02 (9) | C3—C2—C1 | 117.3 (2) |
O1—Mn1—O3 | 158.23 (6) | C7—C2—C1 | 124.7 (2) |
O6—Mn1—O3 | 99.81 (8) | C4—C3—C2 | 123.2 (3) |
O5—Mn1—O3 | 87.67 (8) | C4—C3—H3 | 118.4 |
O1—Mn1—N1 | 83.55 (7) | C2—C3—H3 | 118.4 |
O6—Mn1—N1 | 174.32 (8) | C3—C4—C5 | 118.3 (2) |
O5—Mn1—N1 | 92.25 (9) | C3—C4—C8 | 120.1 (3) |
O3—Mn1—N1 | 75.06 (7) | C5—C4—C8 | 121.6 (3) |
O1—Mn1—O7 | 89.27 (8) | C6—C5—C4 | 121.0 (3) |
O6—Mn1—O7 | 86.44 (8) | C6—C5—H5 | 119.5 |
O5—Mn1—O7 | 170.11 (8) | C4—C5—H5 | 119.5 |
O3—Mn1—O7 | 88.87 (7) | C5—C6—C7 | 121.8 (3) |
N1—Mn1—O7 | 95.81 (7) | C5—C6—H6 | 119.1 |
C1—N1—C9 | 118.2 (2) | C7—C6—H6 | 119.1 |
C1—N1—Mn1 | 126.74 (17) | O1—C7—C6 | 119.0 (2) |
C9—N1—Mn1 | 114.38 (14) | O1—C7—C2 | 123.2 (2) |
C7—O1—Mn1 | 132.77 (16) | C6—C7—C2 | 117.7 (2) |
C10—O3—Mn1 | 119.94 (16) | O2—C8—C4 | 125.3 (3) |
Mn1—O5—H5A | 119.8 (17) | O2—C8—H8 | 117.3 |
Mn1—O5—H5B | 133.8 (17) | C4—C8—H8 | 117.3 |
H5A—O5—H5B | 106.4 (15) | N1—C9—C10 | 111.97 (19) |
Mn1—O6—H6A | 129.7 (17) | N1—C9—H9A | 109.2 |
Mn1—O6—H6B | 118.2 (17) | C10—C9—H9A | 109.2 |
H6A—O6—H6B | 106.6 (14) | N1—C9—H9B | 109.2 |
Mn1—O7—H7A | 119 (2) | C10—C9—H9B | 109.2 |
Mn1—O7—H7B | 108.5 (19) | H9A—C9—H9B | 107.9 |
H7A—O7—H7B | 107.1 (15) | O4—C10—O3 | 124.4 (2) |
H8A—O8—H8B | 107.6 (15) | O4—C10—C9 | 117.0 (2) |
N1—C1—C2 | 126.7 (2) | O3—C10—C9 | 118.6 (2) |
N1—C1—H1 | 116.7 |
D—H···A | D—H | H···A | D···A | D—H···A |
O7—H7A···O3i | 0.84 (1) | 1.93 (1) | 2.758 (3) | 172 (3) |
O6—H6B···O4ii | 0.84 (1) | 2.28 (2) | 3.014 (3) | 146 (2) |
O6—H6A···O4i | 0.85 (1) | 1.83 (1) | 2.677 (3) | 177 (3) |
O5—H5B···O1iii | 0.84 (1) | 1.89 (1) | 2.723 (3) | 172 (2) |
O8—H8B···O2iv | 0.84 (1) | 2.00 (1) | 2.793 (3) | 157 (3) |
O5—H5A···O8v | 0.85 (1) | 1.83 (1) | 2.669 (3) | 169 (3) |
O7—H7B···O4vi | 0.85 (1) | 1.90 (1) | 2.746 (3) | 172 (3) |
O8—H8A···O7 | 0.84 (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. |
Experimental details
Crystal data | |
Chemical formula | [Mn(C10H7NO4)(H2O)3]·H2O |
Mr | 332.17 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 293 |
a, b, c (Å) | 11.208 (5), 7.890 (3), 31.212 (13) |
V (Å3) | 2760 (2) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.99 |
Crystal size (mm) | 0.20 × 0.15 × 0.05 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 1998) |
Tmin, Tmax | 0.836, 0.952 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12431, 3016, 2197 |
Rint | 0.050 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.100, 1.04 |
No. of reflections | 2999 |
No. of parameters | 205 |
No. of restraints | 12 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.34, −0.52 |
Computer programs: SMART (Bruker, 1998), SMART, SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
O7—H7A···O3i | 0.836 (9) | 1.928 (11) | 2.758 (3) | 172 (3) |
O6—H6B···O4ii | 0.840 (9) | 2.281 (17) | 3.014 (3) | 146 (2) |
O6—H6A···O4i | 0.847 (9) | 1.831 (10) | 2.677 (3) | 177 (3) |
O5—H5B···O1iii | 0.843 (10) | 1.886 (11) | 2.723 (3) | 172 (2) |
O8—H8B···O2iv | 0.844 (10) | 1.997 (13) | 2.793 (3) | 157 (3) |
O5—H5A···O8v | 0.847 (10) | 1.833 (10) | 2.669 (3) | 169 (3) |
O7—H7B···O4vi | 0.848 (10) | 1.904 (11) | 2.746 (3) | 172 (3) |
O8—H8A···O7 | 0.843 (10) | 2.087 (13) | 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. |
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.