Triaqua­[2-(carboxyl­atomethyl­imino­meth­yl)-4-formyl­phenolato-κ3O,N,O′]manganese(II) monohydrate

Cai, J.-H.

doi:10.1107/S1600536807021824

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Triaqua[2-(carboxylatomethyliminomethyl)-4-formylphenolato-κ³O,N,O′]manganese(II) monohydrate

J.-H. Cai

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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807021824/ng2264sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807021824/ng2264Isup2.hkl Contains datablock I

CCDC reference: 650611

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.039
wR factor = 0.100
Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O3     -   C10     ..       5.50 su
PLAT245_ALERT_2_C U(iso) H8A     Smaller than U(eq) O8      by ...       0.01 AngSq
PLAT245_ALERT_2_C U(iso) H8B     Smaller than U(eq) O8      by ...       0.01 AngSq

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT794_ALERT_5_G Check Predicted Bond Valency for Mn1         (2)       2.23
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         12

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   4 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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.

Structure description 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).

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

	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.

Triaqua[2-(carboxylatomethyliminomethyl)-4-formylphenolato- κ³O,N,O']manganese(II) monohydrate top

Crystal data top

[Mn(C₁₀H₇NO₄)(H₂O)₃]·H₂O	F(000) = 1368
M_r = 332.17	D_x = 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

Data collection top

Bruker SMART CCD area-detector diffractometer	3016 independent reflections
Radiation source: fine-focus sealed tube	2197 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
φ and ω scans	θ_max = 27.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −5→14
T_min = 0.836, T_max = 0.952	k = −9→10
12431 measured reflections	l = −39→38

Refinement top

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(F_o²) + (0.0509P)² + 0.4197P] where P = (F_o² + 2F_c²)/3
2999 reflections	(Δ/σ)_max = 0.001
205 parameters	Δρ_max = 0.34 e Å⁻³
12 restraints	Δρ_min = −0.52 e Å⁻³

Crystal data top

[Mn(C₁₀H₇NO₄)(H₂O)₃]·H₂O	V = 2760 (2) Å³
M_r = 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

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)
T_min = 0.836, T_max = 0.952	R_int = 0.050
12431 measured reflections

Refinement top

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	Δρ_max = 0.34 e Å⁻³
2999 reflections	Δρ_min = −0.52 e Å⁻³
205 parameters

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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···O2^iv	0.84 (1)	2.00 (1)	2.793 (3)	157 (3)
O5—H5A···O8^v	0.85 (1)	1.83 (1)	2.669 (3)	169 (3)
O7—H7B···O4^vi	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
M_r	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)
T_min, T_max	0.836, 0.952
No. of measured, independent and observed [I > 2σ(I)] reflections	12431, 3016, 2197
R_int	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
Δρ_max, Δρ_min (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.

Hydrogen-bond geometry (Å, º) top

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···O2^iv	0.844 (10)	1.997 (13)	2.793 (3)	157 (3)
O5—H5A···O8^v	0.847 (10)	1.833 (10)	2.669 (3)	169 (3)
O7—H7B···O4^vi	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.

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