(Acetyl-acetonato-κO,O')-aqua-[salicyl-aldehyde nicotinoylhydrazonato(2-)-κO,N,O']manganese(III).

The Mn(III) atom in the title complex, [Mn(C(13)H(9)N(3)O(2))(C(5)H(7)O(2))(H(2)O)], is coordinated by three donors from a dianionic ligand, salicylaldehyde nicotylhydrazone, two O atoms from an acetyl-acetonate anion and a water mol-ecule in a distorted octa-hedral geometry. There is an extended two-dimensional supra-molecular motif resulting from O-H⋯N hydrogen bonds between the coordinated water mol-ecule and a hydrazine N or pyridine N atom, and from C-H⋯O hydrogen bonds between a CH group and the phenolate O atom.

Related literature

For general background, see: Janiak (2003 ▶); Kitagawa et al. (2004 ▶); Graham & Pike (2000 ▶); Niu et al. (2005 ▶); Adams et al. (2000 ▶); Ranford et al. (1998 ▶); Batten & Robson (1998 ▶); Hagrman et al. (1999 ▶). For related structures, see: Kessissoglou et al. (2002 ▶); Sailaja et al. (2003 ▶); Zhang et al. (2001 ▶); Clérac et al. (2002 ▶); Mitra et al. (2006 ▶); Hoshino et al. (2003 ▶); Nakamura et al. (2001 ▶); Liu et al. (2001 ▶).

Experimental

Crystal data

[Mn(C13H9N3O2)(C5H7O2)(H2O)]

M = 411.29

Monoclinic,

a = 17.462 (2) Å

b = 9.5286 (18) Å

c = 11.529 (3) Å

β = 106.798 (5)°

V = 1836.4 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.75 mm−1

T = 293 (2) K

0.58 × 0.49 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: multi-scan (TEXRAY; Molecular Structure Corporation, 1999 ▶) T min = 0.598, T max = 0.932

17468 measured reflections

4203 independent reflections

3380 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.105

S = 1.06

4203 reflections

246 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.26 e Å−3

Data collection: TEXRAY (Molecular Structure Corporation, 1999 ▶); cell refinement: TEXRAY; data reduction: TEXSAN (Mol­ecular Structure Corporation, 1999 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEX (McArdle, 1995 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807060734/xu2362sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807060734/xu2362Isup2.hkl

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

[Mn(C13H9N3O2)(C5H7O2)(H2O)]	F000 = 848
Mr = 411.29	Dx = 1.488 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 17468 reflections
a = 17.462 (2) Å	θ = 3.2–27.5º
b = 9.5286 (18) Å	µ = 0.75 mm−1
c = 11.529 (3) Å	T = 293 (2) K
β = 106.798 (5)º	Block, black
V = 1836.4 (6) Å3	0.58 × 0.49 × 0.10 mm
Z = 4

Rigaku R-AXIS RAPID IP diffractometer	4203 independent reflections
Radiation source: fine-focus sealed tube	3380 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.047
T = 293(2) K	θmax = 27.5º
ω scans	θmin = 3.2º
Absorption correction: multi-scan(TEXRAY; Molecular Structure Corporation, 1999)	h = −22→22
Tmin = 0.598, Tmax = 0.932	k = −12→12
17468 measured reflections	l = −12→14

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039	H-atom parameters constrained
wR(F2) = 0.105	w = 1/[σ2(Fo2) + (0.056P)2 + 0.2426P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
4203 reflections	Δρmax = 0.40 e Å−3
246 parameters	Δρmin = −0.26 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
Mn1	0.249798 (18)	0.57337 (3)	0.43657 (2)	0.03214 (11)
O1	0.34284 (9)	0.48904 (15)	0.40574 (12)	0.0409 (3)
O2	0.15564 (9)	0.67021 (14)	0.43678 (12)	0.0384 (3)
O3	0.19055 (11)	0.37673 (16)	0.40212 (15)	0.0509 (4)
O4	0.27874 (10)	0.52725 (15)	0.60578 (12)	0.0419 (3)
O5	0.32467 (9)	0.77095 (14)	0.50465 (13)	0.0405 (3)
H5B	0.3069	0.8261	0.5550	0.061*
H5C	0.3709	0.7356	0.5472	0.061*
N1	0.53617 (13)	0.3198 (2)	0.3250 (2)	0.0579 (5)
N2	0.29071 (10)	0.57484 (16)	0.21251 (15)	0.0343 (4)
N3	0.23512 (10)	0.63091 (16)	0.26725 (13)	0.0302 (3)
C1	0.47353 (14)	0.3815 (2)	0.3467 (2)	0.0463 (5)
H1B	0.4732	0.3895	0.4269	0.056*
C2	0.40938 (13)	0.43433 (19)	0.25884 (19)	0.0373 (4)
C3	0.41031 (18)	0.4214 (3)	0.1385 (2)	0.0572 (7)
H3A	0.3677	0.4534	0.0753	0.069*
C4	0.4756 (2)	0.3604 (3)	0.1159 (3)	0.0716 (9)
H4A	0.4781	0.3518	0.0367	0.086*
C5	0.53676 (18)	0.3125 (3)	0.2098 (3)	0.0658 (7)
H5A	0.5810	0.2730	0.1928	0.079*
C6	0.34313 (12)	0.50249 (19)	0.29342 (17)	0.0343 (4)
C7	0.18497 (12)	0.7207 (2)	0.20497 (17)	0.0337 (4)
H7A	0.1885	0.7435	0.1283	0.040*
C8	0.12392 (12)	0.78839 (19)	0.24536 (17)	0.0332 (4)
C9	0.11051 (12)	0.75715 (18)	0.35741 (17)	0.0331 (4)
C10	0.04471 (14)	0.8204 (2)	0.3828 (2)	0.0440 (5)
H10A	0.0341	0.8006	0.4556	0.053*
C11	−0.00431 (15)	0.9108 (2)	0.3023 (2)	0.0490 (6)
H11A	−0.0482	0.9499	0.3207	0.059*
C12	0.01056 (15)	0.9450 (2)	0.1939 (2)	0.0511 (6)
H12A	−0.0224	1.0081	0.1407	0.061*
C13	0.07387 (14)	0.8852 (2)	0.1662 (2)	0.0436 (5)
H13A	0.0843	0.9086	0.0939	0.052*
C14	0.1360 (2)	0.1594 (3)	0.4358 (3)	0.0801 (9)
H14A	0.1246	0.1535	0.3493	0.120*
H14B	0.0867	0.1641	0.4569	0.120*
H14C	0.1655	0.0779	0.4724	0.120*
C15	0.18474 (15)	0.2891 (2)	0.4808 (2)	0.0499 (6)
C16	0.22056 (18)	0.3043 (2)	0.6060 (2)	0.0586 (7)
H16A	0.2100	0.2300	0.6570	0.070*
C17	0.26526 (15)	0.4158 (2)	0.6601 (2)	0.0449 (5)
C18	0.3042 (2)	0.4170 (3)	0.7940 (2)	0.0728 (9)
H18A	0.3610	0.4275	0.8098	0.109*
H18B	0.2930	0.3304	0.8284	0.109*
H18C	0.2836	0.4940	0.8297	0.109*

	U11	U22	U33	U12	U13	U23
Mn1	0.03229 (18)	0.03714 (17)	0.02695 (16)	0.00286 (12)	0.00849 (12)	0.00486 (11)
O1	0.0407 (9)	0.0492 (8)	0.0326 (7)	0.0147 (7)	0.0103 (6)	0.0088 (6)
O2	0.0359 (8)	0.0488 (8)	0.0325 (7)	0.0063 (6)	0.0132 (6)	0.0050 (6)
O3	0.0556 (11)	0.0453 (8)	0.0487 (9)	−0.0095 (7)	0.0102 (8)	−0.0057 (7)
O4	0.0515 (10)	0.0417 (7)	0.0303 (7)	−0.0014 (7)	0.0081 (6)	0.0076 (6)
O5	0.0358 (8)	0.0441 (7)	0.0390 (7)	−0.0016 (6)	0.0068 (6)	0.0023 (6)
N1	0.0410 (12)	0.0618 (12)	0.0654 (13)	0.0187 (10)	0.0068 (10)	−0.0026 (11)
N2	0.0316 (9)	0.0408 (8)	0.0320 (8)	0.0060 (7)	0.0114 (7)	0.0021 (7)
N3	0.0281 (9)	0.0343 (7)	0.0285 (7)	0.0030 (6)	0.0085 (7)	0.0023 (6)
C1	0.0413 (13)	0.0515 (11)	0.0425 (12)	0.0088 (10)	0.0065 (10)	−0.0033 (10)
C2	0.0362 (11)	0.0349 (9)	0.0403 (11)	0.0063 (8)	0.0105 (9)	−0.0002 (8)
C3	0.0633 (17)	0.0670 (15)	0.0411 (12)	0.0315 (13)	0.0148 (12)	0.0041 (11)
C4	0.082 (2)	0.0829 (19)	0.0559 (15)	0.0405 (17)	0.0301 (15)	0.0051 (14)
C5	0.0575 (18)	0.0671 (15)	0.0785 (19)	0.0266 (13)	0.0286 (15)	−0.0014 (14)
C6	0.0331 (11)	0.0338 (9)	0.0349 (10)	0.0011 (8)	0.0083 (8)	−0.0006 (8)
C7	0.0321 (10)	0.0404 (9)	0.0286 (9)	0.0020 (8)	0.0085 (8)	0.0036 (8)
C8	0.0309 (10)	0.0344 (9)	0.0334 (9)	0.0025 (8)	0.0079 (8)	0.0000 (8)
C9	0.0298 (10)	0.0333 (9)	0.0350 (9)	−0.0024 (7)	0.0077 (8)	−0.0033 (8)
C10	0.0406 (13)	0.0499 (11)	0.0453 (11)	0.0033 (10)	0.0187 (10)	−0.0017 (9)
C11	0.0386 (13)	0.0503 (12)	0.0609 (14)	0.0122 (10)	0.0188 (11)	−0.0025 (11)
C12	0.0458 (14)	0.0495 (12)	0.0545 (14)	0.0175 (10)	0.0088 (11)	0.0057 (10)
C13	0.0438 (13)	0.0443 (10)	0.0417 (11)	0.0098 (9)	0.0108 (10)	0.0044 (9)
C14	0.083 (2)	0.0524 (14)	0.104 (2)	−0.0233 (15)	0.026 (2)	−0.0089 (15)
C15	0.0479 (14)	0.0353 (10)	0.0687 (15)	−0.0019 (9)	0.0199 (12)	−0.0020 (10)
C16	0.0756 (19)	0.0434 (11)	0.0589 (15)	−0.0054 (12)	0.0228 (14)	0.0148 (11)
C17	0.0494 (14)	0.0463 (11)	0.0412 (11)	0.0074 (10)	0.0166 (10)	0.0130 (9)
C18	0.101 (3)	0.0729 (17)	0.0410 (14)	−0.0015 (16)	0.0143 (15)	0.0194 (12)

Mn1—O2	1.8860 (14)	C5—H5A	0.9300
Mn1—O4	1.9195 (14)	C7—C8	1.434 (3)
Mn1—O1	1.9354 (14)	C7—H7A	0.9300
Mn1—N3	1.9718 (16)	C8—C9	1.410 (3)
Mn1—O3	2.1216 (16)	C8—C13	1.410 (3)
Mn1—O5	2.2971 (14)	C9—C10	1.401 (3)
O1—C6	1.303 (2)	C10—C11	1.370 (3)
O2—C9	1.315 (2)	C10—H10A	0.9300
O3—C15	1.259 (3)	C11—C12	1.388 (3)
O4—C17	1.289 (2)	C11—H11A	0.9300
O5—H5B	0.9021	C12—C13	1.361 (3)
O5—H5C	0.8812	C12—H12A	0.9300
N1—C1	1.327 (3)	C13—H13A	0.9300
N1—C5	1.333 (4)	C14—C15	1.505 (3)
N2—C6	1.300 (3)	C14—H14A	0.9600
N2—N3	1.407 (2)	C14—H14B	0.9600
N3—C7	1.285 (2)	C14—H14C	0.9600
C1—C2	1.370 (3)	C15—C16	1.405 (4)
C1—H1B	0.9300	C16—C17	1.358 (3)
C2—C3	1.398 (3)	C16—H16A	0.9713
C2—C6	1.478 (3)	C17—C18	1.497 (4)
C3—C4	1.370 (4)	C18—H18A	0.9600
C3—H3A	0.9300	C18—H18B	0.9600
C4—C5	1.361 (4)	C18—H18C	0.9600
C4—H4A	0.9300
O2—Mn1—O4	94.83 (6)	O1—C6—C2	116.94 (17)
O2—Mn1—O1	169.05 (6)	N3—C7—C8	124.64 (17)
O4—Mn1—O1	95.92 (6)	N3—C7—H7A	117.7
O2—Mn1—N3	90.07 (6)	C8—C7—H7A	117.7
O4—Mn1—N3	172.13 (7)	C9—C8—C13	119.71 (18)
O1—Mn1—N3	79.02 (6)	C9—C8—C7	122.60 (17)
O2—Mn1—O3	93.11 (7)	C13—C8—C7	117.64 (17)
O4—Mn1—O3	87.65 (6)	O2—C9—C10	119.25 (17)
O1—Mn1—O3	89.36 (7)	O2—C9—C8	123.10 (17)
N3—Mn1—O3	98.24 (6)	C10—C9—C8	117.64 (18)
O2—Mn1—O5	90.51 (6)	C11—C10—C9	121.3 (2)
O4—Mn1—O5	83.32 (6)	C11—C10—H10A	119.4
O1—Mn1—O5	88.73 (6)	C9—C10—H10A	119.4
N3—Mn1—O5	90.50 (6)	C10—C11—C12	121.0 (2)
O3—Mn1—O5	170.53 (6)	C10—C11—H11A	119.5
C6—O1—Mn1	112.73 (12)	C12—C11—H11A	119.5
C9—O2—Mn1	130.91 (12)	C13—C12—C11	119.3 (2)
C15—O3—Mn1	125.99 (15)	C13—C12—H12A	120.3
C17—O4—Mn1	130.61 (15)	C11—C12—H12A	120.3
Mn1—O5—H5B	115.4	C12—C13—C8	121.0 (2)
Mn1—O5—H5C	102.5	C12—C13—H13A	119.5
H5B—O5—H5C	107.1	C8—C13—H13A	119.5
C1—N1—C5	117.0 (2)	C15—C14—H14A	109.5
C6—N2—N3	108.27 (16)	C15—C14—H14B	109.5
C7—N3—N2	116.70 (15)	H14A—C14—H14B	109.5
C7—N3—Mn1	127.66 (13)	C15—C14—H14C	109.5
N2—N3—Mn1	115.42 (11)	H14A—C14—H14C	109.5
N1—C1—C2	124.5 (2)	H14B—C14—H14C	109.5
N1—C1—H1B	117.8	O3—C15—C16	124.6 (2)
C2—C1—H1B	117.8	O3—C15—C14	116.8 (2)
C1—C2—C3	117.4 (2)	C16—C15—C14	118.6 (2)
C1—C2—C6	119.89 (19)	C17—C16—C15	125.3 (2)
C3—C2—C6	122.7 (2)	C17—C16—H16A	118.4
C4—C3—C2	118.3 (2)	C15—C16—H16A	116.2
C4—C3—H3A	120.8	O4—C17—C16	125.7 (2)
C2—C3—H3A	120.8	O4—C17—C18	113.7 (2)
C5—C4—C3	119.7 (2)	C16—C17—C18	120.6 (2)
C5—C4—H4A	120.1	C17—C18—H18A	109.5
C3—C4—H4A	120.1	C17—C18—H18B	109.5
N1—C5—C4	123.0 (2)	H18A—C18—H18B	109.5
N1—C5—H5A	118.5	C17—C18—H18C	109.5
C4—C5—H5A	118.5	H18A—C18—H18C	109.5
N2—C6—O1	124.14 (18)	H18B—C18—H18C	109.5
N2—C6—C2	118.88 (17)
O2—Mn1—O1—C6	−10.2 (4)	C3—C4—C5—N1	1.1 (5)
O4—Mn1—O1—C6	−179.52 (14)	N3—N2—C6—O1	−1.1 (3)
N3—Mn1—O1—C6	−5.61 (13)	N3—N2—C6—C2	−178.91 (16)
O3—Mn1—O1—C6	92.91 (14)	Mn1—O1—C6—N2	5.6 (3)
O5—Mn1—O1—C6	−96.37 (14)	Mn1—O1—C6—C2	−176.53 (13)
O4—Mn1—O2—C9	164.44 (17)	C1—C2—C6—N2	167.1 (2)
O1—Mn1—O2—C9	−4.9 (4)	C3—C2—C6—N2	−12.4 (3)
N3—Mn1—O2—C9	−9.40 (17)	C1—C2—C6—O1	−10.8 (3)
O3—Mn1—O2—C9	−107.66 (17)	C3—C2—C6—O1	169.6 (2)
O5—Mn1—O2—C9	81.10 (17)	N2—N3—C7—C8	179.71 (17)
O2—Mn1—O3—C15	−92.8 (2)	Mn1—N3—C7—C8	−6.0 (3)
O4—Mn1—O3—C15	1.9 (2)	N3—C7—C8—C9	−3.1 (3)
O1—Mn1—O3—C15	97.8 (2)	N3—C7—C8—C13	179.7 (2)
N3—Mn1—O3—C15	176.63 (19)	Mn1—O2—C9—C10	−177.10 (14)
O2—Mn1—O4—C17	95.0 (2)	Mn1—O2—C9—C8	4.3 (3)
O1—Mn1—O4—C17	−87.0 (2)	C13—C8—C9—O2	−178.60 (19)
O3—Mn1—O4—C17	2.1 (2)	C7—C8—C9—O2	4.2 (3)
O5—Mn1—O4—C17	−175.0 (2)	C13—C8—C9—C10	2.8 (3)
C6—N2—N3—C7	171.09 (17)	C7—C8—C9—C10	−174.42 (19)
C6—N2—N3—Mn1	−3.94 (19)	O2—C9—C10—C11	−179.5 (2)
O2—Mn1—N3—C7	10.08 (18)	C8—C9—C10—C11	−0.8 (3)
O1—Mn1—N3—C7	−169.04 (18)	C9—C10—C11—C12	−1.3 (4)
O3—Mn1—N3—C7	103.23 (18)	C10—C11—C12—C13	1.4 (4)
O5—Mn1—N3—C7	−80.43 (18)	C11—C12—C13—C8	0.6 (4)
O2—Mn1—N3—N2	−175.53 (13)	C9—C8—C13—C12	−2.7 (3)
O1—Mn1—N3—N2	5.34 (12)	C7—C8—C13—C12	174.6 (2)
O3—Mn1—N3—N2	−82.38 (13)	Mn1—O3—C15—C16	−3.4 (4)
O5—Mn1—N3—N2	93.96 (13)	Mn1—O3—C15—C14	176.78 (19)
C5—N1—C1—C2	1.7 (4)	O3—C15—C16—C17	1.0 (4)
N1—C1—C2—C3	0.2 (4)	C14—C15—C16—C17	−179.2 (3)
N1—C1—C2—C6	−179.3 (2)	Mn1—O4—C17—C16	−4.8 (4)
C1—C2—C3—C4	−1.6 (4)	Mn1—O4—C17—C18	175.20 (19)
C6—C2—C3—C4	178.0 (2)	C15—C16—C17—O4	3.3 (4)
C2—C3—C4—C5	1.0 (5)	C15—C16—C17—C18	−176.7 (3)
C1—N1—C5—C4	−2.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5B···N2i	0.90	2.14	3.013 (2)	164
O5—H5C···N1ii	0.88	1.92	2.784 (3)	165
C7—H7A···O2iii	0.93	2.27	3.160 (2)	160
C13—H13A···O2iii	0.93	2.59	3.390 (3)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5B⋯N2i	0.90	2.14	3.013 (2)	164
O5—H5C⋯N1ii	0.88	1.92	2.784 (3)	165
C7—H7A⋯O2iii	0.93	2.27	3.160 (2)	160
C13—H13A⋯O2iii	0.93	2.59	3.390 (3)	145

Symmetry codes: (i) ; (ii) ; (iii) .