(Acetyl-acetonato-κO,O')aqua-[2-(2-nitro-phen-oxy)-N'-(2-oxidobenzyl-idene-κO)acetohydrazidato-κO,N']manganese(III).

In the title complex, [Mn(C(15)H(11)N(3)O(5))(C(5)H(7)O(2))(H(2)O)], the Mn(III) ion has a distorted octa-hedral coordination geometry. It is coordinated by a phen-oxy O atom, a hydrazine N atom and a carbonyl O atom of the 2-(2-nitro-phen-oxy)-N'-(2-oxidobenzyl-idene-κO)acetohydrazidate dianion, by two O atoms of the acetyl-acetonate anion and by the O atom of a coordinated water mol-ecule. In the crystal structure, complex mol-ecules are linked into centrosymmetric dimeric units through four inter-molecular O-H⋯O hydrogen bonds involving both H atoms of the coordinated water mol-ecule.

Related literature

For the biological activity and chemical versatility of hydrazone complexes, see: Liu & Gao (1998 ▶); Iskander et al. (2001 ▶); Cariati et al. (2002 ▶); Sreekanth et al. (2004 ▶); Bai et al. (2006 ▶); Mondal et al. (2008 ▶). For phenoxy­acetyl­hydrazone complexes, see: Chen & Liu (2004 ▶); Sun et al. (2005 ▶); Chen & Liu (2006 ▶).

Experimental

Crystal data

[Mn(C15H11N3O5)(C5H7O2)(H2O)]

M = 485.33

Monoclinic,

a = 8.5217 (6) Å

b = 13.9263 (10) Å

c = 17.6311 (10) Å

β = 92.725 (3)°

V = 2090.0 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.69 mm−1

T = 293 K

0.58 × 0.32 × 0.27 mm

Data collection

Rigaku R-AXIS RAPID Imaging Plate diffractometer

Absorption correction: multi-scan (TEXRAY; Molecular Structure Corporation, 1999 ▶) T min = 0.766, T max = 0.832

4921 measured reflections

4735 independent reflections

3155 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.086

S = 0.88

4735 reflections

293 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.41 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: SHELXS98 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL98 (Sheldrick, 2008 ▶); molecular graphics: ORTEX (McArdle, 1995 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809028177/fj2221sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809028177/fj2221Isup2.hkl

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

[Mn(C15H11N3O5)(C5H7O2)(H2O)]	F(000) = 1000
Mr = 485.33	Dx = 1.542 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4921 reflections
a = 8.5217 (6) Å	θ = 2.3–27.5°
b = 13.9263 (10) Å	µ = 0.69 mm−1
c = 17.6311 (10) Å	T = 293 K
β = 92.725 (3)°	Prism, red-black
V = 2090.0 (2) Å3	0.58 × 0.32 × 0.27 mm
Z = 4

Rigaku R-AXIS RAPID Imaging Plate diffractometer	4735 independent reflections
Radiation source: fine-focus sealed tube	3155 reflections with I > 2σ(I)
graphite	Rint = 0.046
ω scans	θmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan (TEXRAY; Molecular Structure Corporation, 1999)	h = 0→11
Tmin = 0.766, Tmax = 0.832	k = 0→18
4735 measured reflections	l = −22→22

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H-atom parameters constrained
S = 0.88	w = 1/[σ2(Fo2) + (0.042P)2] where P = (Fo2 + 2Fc2)/3
4735 reflections	(Δ/σ)max < 0.001
293 parameters	Δρmax = 0.41 e Å−3
2 restraints	Δρmin = −0.26 e Å−3

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	0.42210 (3)	0.18422 (2)	0.481380 (18)	0.03308 (10)
N1	0.57698 (19)	0.27034 (12)	0.53316 (9)	0.0331 (4)
N2	0.73611 (19)	0.24037 (13)	0.53073 (10)	0.0375 (4)
N3	0.8041 (2)	0.02849 (16)	0.26015 (12)	0.0533 (5)
O1	0.25674 (16)	0.25554 (11)	0.52037 (9)	0.0418 (4)
O2	0.61556 (15)	0.11671 (10)	0.46352 (8)	0.0378 (3)
O3	0.90604 (16)	0.07570 (10)	0.41027 (8)	0.0388 (3)
O4	0.8243 (2)	−0.04084 (13)	0.30114 (10)	0.0592 (5)
O5	0.7271 (3)	0.02349 (18)	0.20070 (14)	0.1154 (10)
O6	0.44030 (18)	0.26593 (11)	0.38003 (9)	0.0456 (4)
O7	0.29877 (16)	0.09269 (10)	0.42284 (8)	0.0378 (3)
O1W	0.39896 (18)	0.07903 (11)	0.57926 (8)	0.0445 (4)
H01	0.3227	0.0898	0.6102	0.084 (10)*
H02	0.3985	0.0165	0.5720	0.059 (8)*
C1	0.2598 (2)	0.34515 (15)	0.54655 (12)	0.0363 (5)
C2	0.3993 (2)	0.39648 (15)	0.56558 (11)	0.0356 (5)
C3	0.3901 (3)	0.49157 (16)	0.59191 (12)	0.0447 (6)
H3A	0.4822	0.5254	0.6036	0.054*
C4	0.2482 (3)	0.53520 (17)	0.60058 (14)	0.0545 (6)
H4A	0.2434	0.5984	0.6173	0.065*
C5	0.1116 (3)	0.48358 (19)	0.58401 (14)	0.0547 (7)
H5A	0.0149	0.5125	0.5907	0.066*
C6	0.1161 (3)	0.39072 (17)	0.55798 (13)	0.0474 (6)
H6A	0.0226	0.3576	0.5478	0.057*
C7	0.5521 (2)	0.35502 (15)	0.55894 (11)	0.0364 (5)
H7A	0.6389	0.3919	0.5743	0.044*
C8	0.7392 (2)	0.16010 (15)	0.49417 (12)	0.0342 (5)
C9	0.8935 (2)	0.10965 (16)	0.48634 (12)	0.0398 (5)
H9A	0.9791	0.1536	0.4990	0.048*
H9B	0.9013	0.0559	0.5213	0.048*
C10	0.9278 (2)	0.14196 (15)	0.35479 (12)	0.0361 (5)
C11	0.8798 (2)	0.11932 (16)	0.27964 (13)	0.0406 (5)
C12	0.9049 (3)	0.18249 (19)	0.22091 (14)	0.0531 (6)
H12A	0.8707	0.1669	0.1716	0.064*
C13	0.9798 (3)	0.26774 (18)	0.23514 (16)	0.0570 (7)
H13A	0.9990	0.3095	0.1955	0.068*
C14	1.0266 (3)	0.29151 (18)	0.30817 (16)	0.0552 (7)
H14A	1.0773	0.3497	0.3177	0.066*
C15	0.9996 (3)	0.23052 (17)	0.36756 (13)	0.0457 (6)
H15A	1.0297	0.2488	0.4169	0.055*
C16	0.4860 (4)	0.28832 (19)	0.25042 (16)	0.0682 (8)
H16A	0.4550	0.3539	0.2572	0.102*
H16B	0.4391	0.2643	0.2036	0.102*
H16C	0.5983	0.2848	0.2489	0.102*
C17	0.4325 (3)	0.22903 (17)	0.31512 (13)	0.0446 (5)
C18	0.3747 (3)	0.13544 (18)	0.29967 (13)	0.0479 (6)
H18A	0.3812	0.1129	0.2503	0.057*
C19	0.3099 (2)	0.07523 (16)	0.35096 (12)	0.0378 (5)
C20	0.2423 (3)	−0.01982 (16)	0.32597 (13)	0.0471 (6)
H20A	0.1363	−0.0249	0.3417	0.071*
H20B	0.3044	−0.0707	0.3486	0.071*
H20C	0.2430	−0.0246	0.2717	0.071*

	U11	U22	U33	U12	U13	U23
Mn1	0.03206 (16)	0.03084 (17)	0.03640 (18)	0.00197 (14)	0.00244 (12)	−0.00560 (15)
N1	0.0330 (9)	0.0332 (10)	0.0331 (9)	0.0030 (7)	0.0021 (8)	−0.0026 (8)
N2	0.0315 (9)	0.0399 (11)	0.0413 (10)	0.0049 (8)	0.0021 (8)	−0.0051 (8)
N3	0.0568 (12)	0.0530 (14)	0.0498 (13)	−0.0075 (11)	−0.0001 (11)	−0.0056 (11)
O1	0.0340 (8)	0.0387 (8)	0.0533 (9)	0.0027 (6)	0.0078 (7)	−0.0123 (7)
O2	0.0343 (7)	0.0318 (8)	0.0475 (9)	0.0009 (6)	0.0037 (7)	−0.0063 (7)
O3	0.0420 (8)	0.0379 (8)	0.0371 (8)	0.0071 (7)	0.0087 (7)	−0.0008 (7)
O4	0.0740 (12)	0.0437 (10)	0.0604 (11)	−0.0057 (9)	0.0091 (9)	−0.0050 (9)
O5	0.158 (2)	0.0944 (18)	0.0865 (16)	−0.0486 (17)	−0.0697 (17)	0.0141 (13)
O6	0.0578 (10)	0.0365 (9)	0.0425 (9)	−0.0007 (7)	0.0016 (8)	0.0018 (7)
O7	0.0405 (8)	0.0375 (8)	0.0353 (8)	−0.0033 (6)	0.0028 (7)	−0.0057 (6)
O1W	0.0534 (9)	0.0368 (9)	0.0437 (9)	0.0019 (7)	0.0092 (8)	−0.0013 (7)
C1	0.0419 (11)	0.0358 (12)	0.0314 (11)	0.0069 (9)	0.0029 (9)	−0.0015 (9)
C2	0.0431 (12)	0.0333 (11)	0.0308 (11)	0.0058 (9)	0.0046 (9)	−0.0037 (9)
C3	0.0544 (14)	0.0377 (13)	0.0417 (13)	0.0053 (11)	0.0009 (11)	−0.0045 (10)
C4	0.0717 (17)	0.0369 (13)	0.0547 (15)	0.0181 (13)	0.0010 (13)	−0.0090 (11)
C5	0.0528 (15)	0.0583 (16)	0.0531 (15)	0.0241 (13)	0.0040 (12)	−0.0089 (13)
C6	0.0435 (12)	0.0493 (14)	0.0496 (14)	0.0105 (11)	0.0046 (11)	−0.0072 (12)
C7	0.0390 (11)	0.0357 (12)	0.0345 (12)	−0.0007 (9)	0.0009 (9)	−0.0056 (10)
C8	0.0368 (11)	0.0346 (12)	0.0317 (11)	0.0044 (9)	0.0055 (9)	0.0018 (9)
C9	0.0390 (11)	0.0450 (13)	0.0356 (11)	0.0108 (10)	0.0033 (10)	0.0003 (10)
C10	0.0312 (10)	0.0357 (12)	0.0418 (12)	0.0075 (9)	0.0060 (9)	0.0010 (10)
C11	0.0383 (11)	0.0377 (12)	0.0458 (13)	0.0023 (10)	0.0029 (10)	0.0002 (11)
C12	0.0585 (15)	0.0573 (16)	0.0432 (13)	0.0045 (13)	0.0004 (12)	0.0036 (12)
C13	0.0642 (16)	0.0482 (16)	0.0591 (17)	0.0034 (13)	0.0090 (14)	0.0146 (13)
C14	0.0601 (15)	0.0359 (13)	0.0701 (18)	−0.0029 (11)	0.0095 (14)	−0.0009 (12)
C15	0.0488 (13)	0.0409 (14)	0.0476 (14)	0.0043 (11)	0.0052 (11)	−0.0057 (11)
C16	0.096 (2)	0.0565 (17)	0.0538 (16)	0.0007 (16)	0.0162 (15)	0.0136 (14)
C17	0.0465 (13)	0.0467 (14)	0.0407 (13)	0.0076 (11)	0.0050 (11)	0.0033 (11)
C18	0.0598 (15)	0.0477 (14)	0.0368 (12)	0.0032 (12)	0.0082 (11)	−0.0041 (11)
C19	0.0361 (11)	0.0377 (12)	0.0394 (12)	0.0066 (9)	−0.0007 (10)	−0.0084 (10)
C20	0.0523 (14)	0.0431 (14)	0.0456 (13)	0.0005 (11)	0.0000 (11)	−0.0126 (11)

Mn1—O1	1.8806 (14)	C5—C6	1.373 (3)
Mn1—O7	1.9214 (14)	C5—H5A	0.9300
Mn1—O2	1.9366 (13)	C6—H6A	0.9300
Mn1—N1	1.9746 (16)	C7—H7A	0.9300
Mn1—O6	2.1303 (15)	C8—C9	1.503 (3)
Mn1—O1W	2.2793 (15)	C9—H9A	0.9700
N1—C7	1.285 (3)	C9—H9B	0.9700
N1—N2	1.421 (2)	C10—C15	1.390 (3)
N2—C8	1.291 (3)	C10—C11	1.404 (3)
N3—O5	1.212 (3)	C11—C12	1.383 (3)
N3—O4	1.213 (2)	C12—C13	1.366 (4)
N3—C11	1.454 (3)	C12—H12A	0.9300
O1—C1	1.330 (2)	C13—C14	1.370 (4)
O2—C8	1.309 (2)	C13—H13A	0.9300
O3—C10	1.364 (2)	C14—C15	1.376 (3)
O3—C9	1.431 (2)	C14—H14A	0.9300
O6—C17	1.253 (3)	C15—H15A	0.9300
O7—C19	1.298 (2)	C16—C17	1.497 (3)
O1W—H01	0.8802	C16—H16A	0.9600
O1W—H02	0.8799	C16—H16B	0.9600
C1—C6	1.402 (3)	C16—H16C	0.9600
C1—C2	1.414 (3)	C17—C18	1.415 (3)
C2—C3	1.407 (3)	C18—C19	1.368 (3)
C2—C7	1.435 (3)	C18—H18A	0.9300
C3—C4	1.368 (3)	C19—C20	1.501 (3)
C3—H3A	0.9300	C20—H20A	0.9600
C4—C5	1.387 (4)	C20—H20B	0.9600
C4—H4A	0.9300	C20—H20C	0.9600
O1—Mn1—O7	98.43 (6)	C2—C7—H7A	117.8
O1—Mn1—O2	166.98 (7)	N2—C8—O2	124.81 (18)
O7—Mn1—O2	92.22 (6)	N2—C8—C9	119.28 (19)
O1—Mn1—N1	90.36 (7)	O2—C8—C9	115.90 (18)
O7—Mn1—N1	171.05 (6)	O3—C9—C8	110.20 (16)
O2—Mn1—N1	79.31 (6)	O3—C9—H9A	109.6
O1—Mn1—O6	96.33 (7)	C8—C9—H9A	109.6
O7—Mn1—O6	87.91 (6)	O3—C9—H9B	109.6
O2—Mn1—O6	91.51 (6)	C8—C9—H9B	109.6
N1—Mn1—O6	89.40 (6)	H9A—C9—H9B	108.1
O1—Mn1—O1W	88.25 (6)	O3—C10—C15	123.9 (2)
O7—Mn1—O1W	85.15 (6)	O3—C10—C11	118.78 (19)
O2—Mn1—O1W	85.19 (6)	C15—C10—C11	117.3 (2)
N1—Mn1—O1W	96.91 (6)	C12—C11—C10	121.0 (2)
O6—Mn1—O1W	172.19 (6)	C12—C11—N3	117.3 (2)
C7—N1—N2	116.98 (17)	C10—C11—N3	121.6 (2)
C7—N1—Mn1	127.08 (14)	C13—C12—C11	120.2 (2)
N2—N1—Mn1	115.18 (12)	C13—C12—H12A	119.9
C8—N2—N1	108.13 (16)	C11—C12—H12A	119.9
O5—N3—O4	121.7 (2)	C12—C13—C14	119.7 (2)
O5—N3—C11	118.1 (2)	C12—C13—H13A	120.2
O4—N3—C11	120.2 (2)	C14—C13—H13A	120.2
C1—O1—Mn1	128.29 (13)	C13—C14—C15	120.9 (2)
C8—O2—Mn1	112.55 (12)	C13—C14—H14A	119.5
C10—O3—C9	117.88 (17)	C15—C14—H14A	119.5
C17—O6—Mn1	122.95 (15)	C14—C15—C10	120.8 (2)
C19—O7—Mn1	125.80 (13)	C14—C15—H15A	119.6
Mn1—O1W—H01	116.9	C10—C15—H15A	119.6
Mn1—O1W—H02	121.7	C17—C16—H16A	109.5
H01—O1W—H02	105.0	C17—C16—H16B	109.5
O1—C1—C6	118.1 (2)	H16A—C16—H16B	109.5
O1—C1—C2	123.98 (18)	C17—C16—H16C	109.5
C6—C1—C2	117.85 (19)	H16A—C16—H16C	109.5
C3—C2—C1	119.68 (19)	H16B—C16—H16C	109.5
C3—C2—C7	118.1 (2)	O6—C17—C18	123.8 (2)
C1—C2—C7	122.25 (18)	O6—C17—C16	117.7 (2)
C4—C3—C2	121.2 (2)	C18—C17—C16	118.5 (2)
C4—C3—H3A	119.4	C19—C18—C17	125.8 (2)
C2—C3—H3A	119.4	C19—C18—H18A	117.1
C3—C4—C5	118.9 (2)	C17—C18—H18A	117.1
C3—C4—H4A	120.5	O7—C19—C18	125.5 (2)
C5—C4—H4A	120.5	O7—C19—C20	113.99 (19)
C6—C5—C4	121.5 (2)	C18—C19—C20	120.5 (2)
C6—C5—H5A	119.3	C19—C20—H20A	109.5
C4—C5—H5A	119.3	C19—C20—H20B	109.5
C5—C6—C1	120.8 (2)	H20A—C20—H20B	109.5
C5—C6—H6A	119.6	C19—C20—H20C	109.5
C1—C6—H6A	119.6	H20A—C20—H20C	109.5
N1—C7—C2	124.32 (19)	H20B—C20—H20C	109.5
N1—C7—H7A	117.8
O1—Mn1—N1—C7	−18.44 (18)	O1—C1—C6—C5	−179.2 (2)
O2—Mn1—N1—C7	169.54 (18)	C2—C1—C6—C5	2.5 (3)
O6—Mn1—N1—C7	77.89 (17)	N2—N1—C7—C2	−179.77 (19)
O1W—Mn1—N1—C7	−106.72 (17)	Mn1—N1—C7—C2	10.7 (3)
O1—Mn1—N1—N2	171.88 (14)	C3—C2—C7—N1	−177.42 (19)
O2—Mn1—N1—N2	−0.15 (13)	C1—C2—C7—N1	2.5 (3)
O6—Mn1—N1—N2	−91.80 (14)	N1—N2—C8—O2	1.6 (3)
O1W—Mn1—N1—N2	83.60 (13)	N1—N2—C8—C9	−177.13 (17)
C7—N1—N2—C8	−171.41 (17)	Mn1—O2—C8—N2	−1.8 (3)
Mn1—N1—N2—C8	−0.6 (2)	Mn1—O2—C8—C9	176.98 (14)
O7—Mn1—O1—C1	−157.85 (17)	C10—O3—C9—C8	71.6 (2)
O2—Mn1—O1—C1	57.6 (4)	N2—C8—C9—O3	−136.04 (19)
N1—Mn1—O1—C1	20.41 (17)	O2—C8—C9—O3	45.1 (2)
O6—Mn1—O1—C1	−69.03 (17)	C9—O3—C10—C15	27.0 (3)
O1W—Mn1—O1—C1	117.32 (17)	C9—O3—C10—C11	−155.01 (18)
O1—Mn1—O2—C8	−37.1 (3)	O3—C10—C11—C12	−177.42 (19)
O7—Mn1—O2—C8	177.99 (13)	C15—C10—C11—C12	0.7 (3)
N1—Mn1—O2—C8	0.91 (13)	O3—C10—C11—N3	1.6 (3)
O6—Mn1—O2—C8	90.02 (14)	C15—C10—C11—N3	179.81 (19)
O1W—Mn1—O2—C8	−97.07 (13)	O5—N3—C11—C12	−21.3 (4)
O1—Mn1—O6—C17	−125.31 (18)	O4—N3—C11—C12	155.4 (2)
O7—Mn1—O6—C17	−27.06 (18)	O5—N3—C11—C10	159.6 (2)
O2—Mn1—O6—C17	65.11 (18)	O4—N3—C11—C10	−23.7 (3)
N1—Mn1—O6—C17	144.40 (18)	C10—C11—C12—C13	1.1 (4)
O1—Mn1—O7—C19	125.06 (16)	N3—C11—C12—C13	−178.0 (2)
O2—Mn1—O7—C19	−62.46 (16)	C11—C12—C13—C14	−1.6 (4)
O6—Mn1—O7—C19	28.97 (16)	C12—C13—C14—C15	0.2 (4)
O1W—Mn1—O7—C19	−147.44 (16)	C13—C14—C15—C10	1.7 (4)
Mn1—O1—C1—C6	166.84 (16)	O3—C10—C15—C14	175.9 (2)
Mn1—O1—C1—C2	−15.0 (3)	C11—C10—C15—C14	−2.2 (3)
O1—C1—C2—C3	179.15 (19)	Mn1—O6—C17—C18	15.6 (3)
C6—C1—C2—C3	−2.6 (3)	Mn1—O6—C17—C16	−165.12 (17)
O1—C1—C2—C7	−0.8 (3)	O6—C17—C18—C19	4.8 (4)
C6—C1—C2—C7	177.4 (2)	C16—C17—C18—C19	−174.5 (2)
C1—C2—C3—C4	1.0 (3)	Mn1—O7—C19—C18	−20.4 (3)
C7—C2—C3—C4	−179.1 (2)	Mn1—O7—C19—C20	160.21 (14)
C2—C3—C4—C5	1.0 (4)	C17—C18—C19—O7	−3.8 (4)
C3—C4—C5—C6	−1.1 (4)	C17—C18—C19—C20	175.6 (2)
C4—C5—C6—C1	−0.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H01···O4i	0.88	2.16	2.955 (2)	150
O1W—H02···O2i	0.88	1.96	2.829 (2)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H01⋯O4i	0.88	2.16	2.955 (2)	150
O1W—H02⋯O2i	0.88	1.96	2.829 (2)	169

Symmetry code: (i) .