Dimeric (2-cyano­phenolato-κO){2,2′-[ethyl­enebis(nitrilo­methyl­idyne)]diphenolato-κ4O,N,N′,O′}manganese(III) monohydrate

Zidane, Y.; Ourari, A.; Mousser, H.; Mousser, A.

doi:10.1107/S1600536811026584

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 8| August 2011| Pages m1069-m1070

doi:10.1107/S1600536811026584

Open

access

Dimeric (2-cyanophenolato-κO){2,2′-[ethylenebis(nitrilomethylidyne)]diphenolato-κ⁴O,N,N′,O′}manganese(III) monohydrate

Youcef Zidane,^a Ali Ourari,^a Hénia Mousser ^b ^* and Abdelhamid Mousser ^c

^aLaboratoire d'Électrochimie, d'Ingénierie Moléculaire et de Catalyse Redox (LEIMCR), Faculté des Sciences de l'Ingénieur, Université Farhat Abbas de Sétif 19000, Algeria, ^bDépartement de Chimie Industrielle, Faculté des Sciences de l'Ingénieur, Université Mentouri Constantine, Campus Chaab Erssas, Constantine, Algeria, and ^cDépartement de Chimie, Faculté des Sciences Exactes, Université Mentouri Constantine, Route de Ain El Bey, Constantine, Algeria
^*Correspondence e-mail: abmousser@yahoo.fr

(Received 6 May 2011; accepted 4 July 2011; online 9 July 2011)

The molecules of the title compound, [Mn(C₇H₄NO)(C₁₆H₁₄N₂O₂)]·H₂O, form dimers in the solid state across a crystallographic inversion center. The bridging Mn₂O₂ group is built of phenoxy groups, and is asymmetric, with an Mn—O distances of 1.9002 (13) and 2.6236 (14) Å. A substantial cavity between the two Mn atoms [Mn⋯Mn = 3.5082 (4) Å] is produced by the formation of the dimer. In the crystal, an extended network of O—H⋯O hydrogen-bonding interactions stabilizes the structure.

Related literature

For related structures, see: Mirkhani et al. (2006 ); Oyaizu et al. (2000 ); Zhang et al. (2009 ). For applications of Mn^II complexes in catalysis, see: Ourari et al. (2006 , 2008 ); Srinivasan et al. (1986 ); Salomao et al. (2007 ); Moutet & Ourari (1997 ). For the synthesis, see: Trivedi et al. (1992 ).

Experimental

Crystal data

[Mn(C₇H₄NO)(C₁₆H₁₂N₂O₂)]·H₂O
M_r = 457.36
Monoclinic, P 2₁ /c
a = 12.8693 (3) Å
b = 14.2487 (3) Å
c = 11.6357 (3) Å
β = 104.297 (1)°
V = 2067.57 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.67 mm⁻¹
T = 293 K
0.08 × 0.06 × 0.04 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
8907 measured reflections
4732 independent reflections
3574 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.103
S = 1.05
4601 reflections
288 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O2	0.86 (4)	2.24 (5)	2.959 (3)	141 (4)
O1W—H2W⋯O3ⁱ	0.96 (4)	1.91 (4)	2.840 (3)	163 (4)
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811026584/om2428sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811026584/om2428Isup2.hkl

checkCIF report

Comment top

Tetradentate Schiff base complexes of transition metals were involved in a large research activity during the last ten years. The complexes of manganese(III) are currently used in catalysis (Ourari et al., 2006; Ourari et al., 2008; Srinivasan et al., 1986; Salomao et al., 2007) and in electrocatalysis reactions (Moutet, et al., 1997). In the present paper, we describe the synthesis and structural study of the dimeric 2-cyanophenoxy{2,2-[ethylenebis-(nitrilomethylidyne)]diphenolato}-manganese(III) monohydrate. The metal fragment in this complex is similar to those described by Mirkhani et al., 2006; Oyaizu et al., 2000; Zhang et al., 2009), where the manganese(III) is chelated by an imidazole moiety, arylcarboxylate group and azide ion, respectively. In the title compound, the manganese(III) atom is chelated by the Schiff base ligand via two N and two O atoms, and is additionally coordinated by a cyanophenoxy group (Fig. 1), forming a distorted MnN₂O₃ square pyramidal arrangement (Table 1). The Schiff base lies in the equatorial plane, and the cyanophenoxy group is in the axial coordination site. The manganese(III) atom is diplaced out of the salen N₂O₂ plane by 0.18Å towards the cyanophenoxy group and confirms that the coordination geometry around the manganese is susceptible to the nature of the axial ligand as described by Oyaizu et al., 2000. In the crystal packing, 2-cyanophenoxy{2,2-[ethylenebis-(nitrilomethylidyne)]diphenolato} -manganese(III) monohydrate forms a solid-state dimer in which the Mn(salen) moiety is linked to its neighbor by two shared cyanophenoxy oxygen atoms. So each manganese(III) achieves a distorted octahedral geometry (Table 1). The Mn—Mn distance is 3.5082 (4)Å. An extended network of O—H···O (Table 2) hydrogen-bonding interactions stabilizes the solid state (Fig. 2). Each dimer is linked to four neighbor dimers via hydrogen water molecule bonds to give layers parallel to (001) plane.

Related literature top

For related structures, see: Mirkhani et al. (2006); Oyaizu et al. (2000); Zhang et al. (2009). For applications of Mn^II complexes in catalysis, see: Ourari et al. (2006, 2008); Srinivasan et al. (1986); Salomao et al. (2007); Moutet & Ourari (1997). For the synthesis, see: Trivedi et al. (1992).

Experimental top

Reagent grade 2-hydroxybenzaldehyde (Aldrich), 1,2-diaminoethane (Fluka) and manganese(II) acetate tetrahydrate (Fluka) were obtained commercially. All the solvents used were of reagent grade. The symmetrical Schiff base was prepared in one step synthesis according to the method described by Trivedi et al., 1992. The ligand was obtained by refluxing a mixture of 2 mmol of 2-hydroxybenzaldehyde and 1 mmol of 1,2-diaminoethane in 25 ml of ethanol for 30 min. A methanolic solution (15 ml) of Mn(Ac)₂, 4H₂O (1 mmol) was added dropwise to the resulting yellow solution containing the ligand. The reaction mixture was stirred continuously for 24 hours under air atmosphere and the mixture was filtered. The filtrate was concentrated to ca. 20 ml under reduced pressure, kept for several weeks at ambient temperature. The brown crystals were collected by filtration and were washed thoroughly with a minimum amount of methanol and dried in air. Yield: (78%).

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with atom labels and 35% probability displacement ellipsoids for non-H atoms. Symmetry codes: i = 1-x, 1-y, 2-z; ii = 0.5+x, 0.5-y, 1+z.
	Fig. 2. The packing of the title compound, viewed down the c axis, showing one layer of molecules connected by O—H···O hydrogen bonds (dashed lines). The phenyl rings and H atoms out of the clusters have been omitted for clarity.

(2-Cyanophenolato-κO){2,2'- [ethylenebis(nitrilomethylidyne)]diphenolato- κ⁴O,N,N',O'}manganese(III) monohydrate top

Crystal data top

[Mn(C₇H₄NO)(C₁₆H₁₄N₂O₂)]·H₂O	F(000) = 944
M_r = 457.36	D_x = 1.469 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3574 reflections
a = 12.8693 (3) Å	θ = 1.0–27.5°
b = 14.2487 (3) Å	µ = 0.67 mm⁻¹
c = 11.6357 (3) Å	T = 293 K
β = 104.297 (1)°	Prism, brown
V = 2067.57 (8) Å³	0.08 × 0.06 × 0.04 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	3574 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.024
Graphite monochromator	θ_max = 27.5°, θ_min = 3.1°
Detector resolution: 8.192 pixels mm^-1	h = −16→16
ω scans	k = −18→18
8907 measured reflections	l = −15→15
4732 independent reflections

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0533P)² + 0.4975P] where P = (F_o² + 2F_c²)/3
4601 reflections	(Δ/σ)_max = 0.003
288 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

[Mn(C₇H₄NO)(C₁₆H₁₄N₂O₂)]·H₂O	V = 2067.57 (8) Å³
M_r = 457.36	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.8693 (3) Å	µ = 0.67 mm⁻¹
b = 14.2487 (3) Å	T = 293 K
c = 11.6357 (3) Å	0.08 × 0.06 × 0.04 mm
β = 104.297 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3574 reflections with I > 2σ(I)
8907 measured reflections	R_int = 0.024
4732 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.36 e Å⁻³
4601 reflections	Δρ_min = −0.42 e Å⁻³
288 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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.

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

	x	y	z	U_iso*/U_eq
Mn1	0.99092 (2)	0.43893 (2)	0.62805 (2)	0.02983 (10)
O1	0.90494 (10)	0.43871 (10)	0.46974 (11)	0.0357 (3)
O2	1.08666 (10)	0.34558 (9)	0.60129 (11)	0.0350 (3)
O3	0.89791 (11)	0.35388 (11)	0.70612 (13)	0.0448 (4)
N1	0.91679 (14)	0.55496 (11)	0.66080 (14)	0.0354 (4)
N2	1.08619 (13)	0.46912 (11)	0.78489 (13)	0.0339 (3)
N3	0.7505 (2)	0.48210 (18)	0.8743 (2)	0.0767 (7)
C1	0.79945 (15)	0.45831 (14)	0.44352 (17)	0.0337 (4)
C2	0.73190 (17)	0.41319 (16)	0.34833 (19)	0.0435 (5)
H2	0.7596	0.3694	0.3046	0.052*
C3	0.62331 (18)	0.43313 (17)	0.3182 (2)	0.0525 (6)
H3	0.5786	0.4019	0.2547	0.063*
C4	0.58015 (18)	0.49842 (19)	0.3805 (2)	0.0568 (6)
H4	0.5068	0.5102	0.3599	0.068*
C5	0.64539 (18)	0.54566 (17)	0.4724 (2)	0.0483 (5)
H5	0.6166	0.5916	0.5122	0.058*
C6	0.75579 (16)	0.52575 (14)	0.50774 (18)	0.0373 (4)
C7	0.82058 (17)	0.57678 (15)	0.60655 (18)	0.0397 (5)
H7	0.7904	0.6294	0.6329	0.048*
C8	0.97976 (19)	0.60968 (15)	0.76127 (19)	0.0445 (5)
H8A	0.9330	0.6482	0.7954	0.053*
H8B	1.0302	0.6502	0.7356	0.053*
C9	1.03842 (19)	0.53916 (16)	0.85072 (18)	0.0426 (5)
H9A	1.0941	0.5700	0.9103	0.051*
H9B	0.9891	0.5089	0.8900	0.051*
C10	1.17722 (17)	0.43171 (15)	0.83253 (17)	0.0387 (4)
H10	1.2138	0.4538	0.9067	0.046*
C11	1.22743 (15)	0.35839 (14)	0.78078 (17)	0.0362 (4)
C12	1.32795 (17)	0.32527 (17)	0.84575 (19)	0.0465 (5)
H12	1.3599	0.3530	0.9182	0.056*
C13	1.38001 (18)	0.25341 (17)	0.8053 (2)	0.0488 (5)
H13	1.4465	0.2327	0.8492	0.059*
C14	1.33099 (18)	0.21203 (16)	0.6970 (2)	0.0460 (5)
H14	1.3648	0.1623	0.6692	0.055*
C15	1.23384 (17)	0.24326 (14)	0.63047 (19)	0.0405 (5)
H15	1.2033	0.2148	0.5581	0.049*
C16	1.17987 (15)	0.31754 (13)	0.66996 (16)	0.0328 (4)
C17	0.80118 (16)	0.31955 (14)	0.66939 (17)	0.0365 (4)
C18	0.7748 (2)	0.25034 (16)	0.5805 (2)	0.0474 (5)
H18	0.8274	0.2283	0.5451	0.057*
C19	0.6724 (2)	0.21485 (19)	0.5453 (2)	0.0584 (6)
H19	0.6570	0.1695	0.4860	0.070*
C20	0.5921 (2)	0.2451 (2)	0.5959 (2)	0.0607 (7)
H20	0.5235	0.2200	0.5715	0.073*
C21	0.61415 (18)	0.31221 (18)	0.6821 (2)	0.0517 (6)
H21	0.5603	0.3329	0.7166	0.062*
C22	0.71671 (17)	0.34976 (15)	0.71865 (18)	0.0404 (5)
C23	0.7380 (2)	0.42338 (17)	0.8061 (2)	0.0514 (6)
O1W	0.9967 (2)	0.18475 (15)	0.44789 (18)	0.0744 (6)
H2W	0.962 (3)	0.185 (3)	0.366 (3)	0.110 (13)*
H1W	1.004 (4)	0.244 (3)	0.461 (4)	0.125 (16)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.03033 (16)	0.03349 (17)	0.02616 (15)	0.00335 (11)	0.00787 (11)	−0.00182 (11)
O1	0.0314 (7)	0.0465 (8)	0.0293 (6)	0.0064 (6)	0.0079 (5)	−0.0036 (6)
O2	0.0332 (7)	0.0383 (7)	0.0326 (7)	0.0049 (6)	0.0061 (5)	−0.0033 (5)
O3	0.0369 (7)	0.0539 (9)	0.0434 (8)	−0.0077 (7)	0.0098 (6)	0.0072 (7)
N1	0.0408 (9)	0.0361 (9)	0.0321 (8)	0.0045 (7)	0.0142 (7)	−0.0014 (7)
N2	0.0382 (9)	0.0366 (8)	0.0276 (8)	−0.0009 (7)	0.0095 (6)	−0.0017 (6)
N3	0.110 (2)	0.0640 (15)	0.0607 (14)	0.0043 (14)	0.0301 (14)	−0.0113 (12)
C1	0.0298 (9)	0.0394 (10)	0.0326 (9)	0.0020 (8)	0.0091 (7)	0.0074 (8)
C2	0.0399 (11)	0.0444 (11)	0.0442 (12)	0.0010 (9)	0.0069 (9)	−0.0002 (9)
C3	0.0380 (12)	0.0519 (14)	0.0613 (14)	−0.0043 (10)	0.0004 (10)	0.0004 (11)
C4	0.0311 (11)	0.0618 (15)	0.0754 (17)	0.0032 (11)	0.0092 (11)	0.0041 (13)
C5	0.0368 (11)	0.0511 (13)	0.0599 (14)	0.0107 (9)	0.0176 (10)	0.0056 (11)
C6	0.0353 (10)	0.0387 (10)	0.0403 (10)	0.0041 (8)	0.0136 (8)	0.0076 (8)
C7	0.0429 (11)	0.0402 (11)	0.0406 (11)	0.0090 (9)	0.0194 (9)	0.0016 (9)
C8	0.0521 (13)	0.0398 (11)	0.0413 (11)	0.0067 (10)	0.0107 (9)	−0.0108 (9)
C9	0.0515 (12)	0.0445 (11)	0.0325 (10)	0.0013 (9)	0.0120 (9)	−0.0093 (8)
C10	0.0403 (11)	0.0452 (11)	0.0273 (9)	−0.0031 (9)	0.0022 (8)	−0.0021 (8)
C11	0.0341 (10)	0.0403 (10)	0.0336 (10)	0.0007 (8)	0.0074 (8)	0.0046 (8)
C12	0.0400 (11)	0.0555 (13)	0.0399 (11)	0.0009 (10)	0.0022 (9)	0.0040 (10)
C13	0.0331 (11)	0.0582 (14)	0.0526 (13)	0.0081 (10)	0.0058 (9)	0.0122 (11)
C14	0.0373 (11)	0.0460 (12)	0.0578 (13)	0.0090 (9)	0.0180 (10)	0.0080 (10)
C15	0.0379 (11)	0.0413 (11)	0.0435 (11)	0.0037 (9)	0.0122 (9)	0.0005 (9)
C16	0.0299 (9)	0.0347 (10)	0.0351 (9)	0.0001 (7)	0.0106 (7)	0.0053 (8)
C17	0.0385 (10)	0.0373 (10)	0.0343 (10)	−0.0023 (8)	0.0099 (8)	0.0085 (8)
C18	0.0549 (14)	0.0459 (12)	0.0447 (12)	−0.0022 (10)	0.0188 (10)	−0.0012 (10)
C19	0.0704 (17)	0.0579 (15)	0.0442 (13)	−0.0176 (13)	0.0089 (12)	−0.0077 (11)
C20	0.0450 (14)	0.0773 (18)	0.0549 (14)	−0.0177 (12)	0.0029 (11)	0.0073 (13)
C21	0.0392 (12)	0.0618 (15)	0.0560 (14)	0.0011 (11)	0.0150 (10)	0.0109 (11)
C22	0.0429 (11)	0.0412 (11)	0.0393 (10)	0.0008 (9)	0.0144 (9)	0.0056 (9)
C23	0.0620 (15)	0.0505 (13)	0.0463 (13)	0.0017 (11)	0.0223 (11)	0.0034 (11)
O1W	0.1058 (17)	0.0567 (12)	0.0507 (11)	0.0004 (11)	0.0002 (11)	−0.0084 (9)

Geometric parameters (Å, º) top

Mn1—O2	1.8903 (13)	C8—H8B	0.9700
Mn1—O1	1.9002 (13)	C9—H9A	0.9700
Mn1—N2	1.9782 (16)	C9—H9B	0.9700
Mn1—N1	1.9921 (16)	C10—C11	1.436 (3)
Mn1—O3	2.0649 (14)	C10—H10	0.9300
Mn1—O1ⁱ	2.6236 (14)	C11—C12	1.409 (3)
O1—C1	1.345 (2)	C11—C16	1.409 (3)
O2—C16	1.328 (2)	C12—C13	1.369 (3)
O3—C17	1.307 (2)	C12—H12	0.9300
N1—C7	1.282 (3)	C13—C14	1.394 (3)
N1—C8	1.471 (3)	C13—H13	0.9300
N2—C10	1.282 (3)	C14—C15	1.372 (3)
N2—C9	1.481 (3)	C14—H14	0.9300
N3—C23	1.137 (3)	C15—C16	1.404 (3)
C1—C2	1.386 (3)	C15—H15	0.9300
C1—C6	1.416 (3)	C17—C18	1.408 (3)
C2—C3	1.384 (3)	C17—C22	1.415 (3)
C2—H2	0.9300	C18—C19	1.377 (4)
C3—C4	1.378 (4)	C18—H18	0.9300
C3—H3	0.9300	C19—C20	1.379 (4)
C4—C5	1.363 (4)	C19—H19	0.9300
C4—H4	0.9300	C20—C21	1.364 (4)
C5—C6	1.407 (3)	C20—H20	0.9300
C5—H5	0.9300	C21—C22	1.390 (3)
C6—C7	1.440 (3)	C21—H21	0.9300
C7—H7	0.9300	C22—C23	1.440 (3)
C8—C9	1.508 (3)	O1W—H2W	0.95 (4)
C8—H8A	0.9700	O1W—H1W	0.85 (4)

O2—Mn1—O1	94.96 (6)	N2—C9—H9A	110.3
O2—Mn1—N2	91.39 (6)	C8—C9—H9A	110.3
O1—Mn1—N2	167.03 (7)	N2—C9—H9B	110.3
O2—Mn1—N1	167.92 (7)	C8—C9—H9B	110.3
O1—Mn1—N1	89.72 (6)	H9A—C9—H9B	108.6
N2—Mn1—N1	81.95 (7)	N2—C10—C11	125.37 (18)
O2—Mn1—O3	97.57 (6)	N2—C10—H10	117.3
O1—Mn1—O3	99.41 (6)	C11—C10—H10	117.3
N2—Mn1—O3	90.94 (6)	C12—C11—C16	119.10 (19)
N1—Mn1—O3	92.63 (6)	C12—C11—C10	117.85 (18)
C1—O1—Mn1	122.21 (11)	C16—C11—C10	123.04 (18)
C16—O2—Mn1	129.88 (12)	C13—C12—C11	121.9 (2)
C17—O3—Mn1	133.20 (13)	C13—C12—H12	119.0
C7—N1—C8	122.58 (17)	C11—C12—H12	119.0
C7—N1—Mn1	123.87 (14)	C12—C13—C14	118.5 (2)
C8—N1—Mn1	113.34 (13)	C12—C13—H13	120.8
C10—N2—C9	120.55 (16)	C14—C13—H13	120.8
C10—N2—Mn1	126.90 (14)	C15—C14—C13	121.3 (2)
C9—N2—Mn1	112.45 (13)	C15—C14—H14	119.4
O1—C1—C2	118.93 (18)	C13—C14—H14	119.4
O1—C1—C6	122.07 (17)	C14—C15—C16	121.0 (2)
C2—C1—C6	118.97 (18)	C14—C15—H15	119.5
C3—C2—C1	120.1 (2)	C16—C15—H15	119.5
C3—C2—H2	119.9	O2—C16—C15	118.44 (18)
C1—C2—H2	119.9	O2—C16—C11	123.35 (17)
C4—C3—C2	121.2 (2)	C15—C16—C11	118.21 (18)
C4—C3—H3	119.4	O3—C17—C18	122.64 (19)
C2—C3—H3	119.4	O3—C17—C22	121.23 (19)
C5—C4—C3	119.7 (2)	C18—C17—C22	116.13 (19)
C5—C4—H4	120.1	C19—C18—C17	121.0 (2)
C3—C4—H4	120.1	C19—C18—H18	119.5
C4—C5—C6	120.8 (2)	C17—C18—H18	119.5
C4—C5—H5	119.6	C18—C19—C20	121.4 (2)
C6—C5—H5	119.6	C18—C19—H19	119.3
C5—C6—C1	119.1 (2)	C20—C19—H19	119.3
C5—C6—C7	118.39 (19)	C21—C20—C19	119.5 (2)
C1—C6—C7	122.49 (18)	C21—C20—H20	120.3
N1—C7—C6	124.71 (19)	C19—C20—H20	120.3
N1—C7—H7	117.6	C20—C21—C22	120.3 (2)
C6—C7—H7	117.6	C20—C21—H21	119.9
N1—C8—C9	106.19 (17)	C22—C21—H21	119.9
N1—C8—H8A	110.5	C21—C22—C17	121.7 (2)
C9—C8—H8A	110.5	C21—C22—C23	119.8 (2)
N1—C8—H8B	110.5	C17—C22—C23	118.5 (2)
C9—C8—H8B	110.5	N3—C23—C22	177.3 (3)
H8A—C8—H8B	108.7	H2W—O1W—H1W	100 (4)
N2—C9—C8	107.04 (16)

O2—Mn1—O1—C1	149.32 (14)	C8—N1—C7—C6	179.83 (19)
N2—Mn1—O1—C1	−91.7 (3)	Mn1—N1—C7—C6	−5.8 (3)
N1—Mn1—O1—C1	−41.83 (15)	C5—C6—C7—N1	167.2 (2)
O3—Mn1—O1—C1	50.79 (15)	C1—C6—C7—N1	−14.3 (3)
O1—Mn1—O2—C16	169.06 (15)	C7—N1—C8—C9	138.9 (2)
N2—Mn1—O2—C16	0.38 (16)	Mn1—N1—C8—C9	−36.0 (2)
N1—Mn1—O2—C16	56.6 (4)	C10—N2—C9—C8	145.0 (2)
O3—Mn1—O2—C16	−90.75 (16)	Mn1—N2—C9—C8	−38.2 (2)
O2—Mn1—O3—C17	−106.03 (19)	N1—C8—C9—N2	46.5 (2)
O1—Mn1—O3—C17	−9.7 (2)	C9—N2—C10—C11	175.19 (19)
N2—Mn1—O3—C17	162.44 (19)	Mn1—N2—C10—C11	−1.0 (3)
N1—Mn1—O3—C17	80.46 (19)	N2—C10—C11—C12	−179.9 (2)
O2—Mn1—N1—C7	140.7 (3)	N2—C10—C11—C16	−1.1 (3)
O1—Mn1—N1—C7	27.74 (16)	C16—C11—C12—C13	−1.2 (3)
N2—Mn1—N1—C7	−162.23 (17)	C10—C11—C12—C13	177.7 (2)
O3—Mn1—N1—C7	−71.66 (17)	C11—C12—C13—C14	−0.4 (3)
O2—Mn1—N1—C8	−44.5 (4)	C12—C13—C14—C15	1.3 (3)
O1—Mn1—N1—C8	−157.44 (14)	C13—C14—C15—C16	−0.6 (3)
N2—Mn1—N1—C8	12.58 (14)	Mn1—O2—C16—C15	177.54 (13)
O3—Mn1—N1—C8	103.15 (14)	Mn1—O2—C16—C11	−2.3 (3)
O2—Mn1—N2—C10	1.26 (17)	C14—C15—C16—O2	179.23 (18)
O1—Mn1—N2—C10	−118.1 (3)	C14—C15—C16—C11	−0.9 (3)
N1—Mn1—N2—C10	−168.63 (18)	C12—C11—C16—O2	−178.37 (18)
O3—Mn1—N2—C10	98.85 (18)	C10—C11—C16—O2	2.8 (3)
O2—Mn1—N2—C9	−175.21 (14)	C12—C11—C16—C15	1.8 (3)
O1—Mn1—N2—C9	65.4 (3)	C10—C11—C16—C15	−177.01 (18)
N1—Mn1—N2—C9	14.90 (13)	Mn1—O3—C17—C18	69.0 (3)
O3—Mn1—N2—C9	−77.62 (14)	Mn1—O3—C17—C22	−111.8 (2)
Mn1—O1—C1—C2	−146.56 (15)	O3—C17—C18—C19	179.1 (2)
Mn1—O1—C1—C6	35.5 (2)	C22—C17—C18—C19	−0.2 (3)
O1—C1—C2—C3	−179.0 (2)	C17—C18—C19—C20	−0.4 (4)
C6—C1—C2—C3	−1.0 (3)	C18—C19—C20—C21	0.5 (4)
C1—C2—C3—C4	0.8 (4)	C19—C20—C21—C22	0.0 (4)
C2—C3—C4—C5	1.1 (4)	C20—C21—C22—C17	−0.7 (4)
C3—C4—C5—C6	−2.7 (4)	C20—C21—C22—C23	177.4 (2)
C4—C5—C6—C1	2.4 (3)	O3—C17—C22—C21	−178.5 (2)
C4—C5—C6—C7	−179.1 (2)	C18—C17—C22—C21	0.8 (3)
O1—C1—C6—C5	177.34 (18)	O3—C17—C22—C23	3.4 (3)
C2—C1—C6—C5	−0.6 (3)	C18—C17—C22—C23	−177.28 (19)
O1—C1—C6—C7	−1.1 (3)	C21—C22—C23—N3	−16 (6)
C2—C1—C6—C7	−179.04 (19)	C17—C22—C23—N3	162 (6)

Symmetry code: (i) −x+1, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O2	0.86 (4)	2.24 (5)	2.959 (3)	141 (4)
O1W—H2W···O3ⁱⁱ	0.96 (4)	1.91 (4)	2.840 (3)	163 (4)

Symmetry code: (ii) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	[Mn(C₇H₄NO)(C₁₆H₁₄N₂O₂)]·H₂O
M_r	457.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	12.8693 (3), 14.2487 (3), 11.6357 (3)
β (°)	104.297 (1)
V (Å³)	2067.57 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.67
Crystal size (mm)	0.08 × 0.06 × 0.04

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8907, 4732, 3574
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.103, 1.05
No. of reflections	4601
No. of parameters	288
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.42

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996).

Selected bond lengths (Å) top

Mn1—O2	1.8903 (13)	Mn1—N1	1.9921 (16)
Mn1—O1	1.9002 (13)	Mn1—O3	2.0649 (14)
Mn1—N2	1.9782 (16)	Mn1—O1ⁱ	2.6236 (14)

Symmetry code: (i) −x+1, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O2	0.86 (4)	2.24 (5)	2.959 (3)	141 (4)
O1W—H2W···O3ⁱⁱ	0.96 (4)	1.91 (4)	2.840 (3)	163 (4)

Symmetry code: (ii) x, −y+1/2, z−1/2.

Acknowledgements

The authors thank the Algerian Ministère de l'Enseignement Supérieur et de la Recherche Scientifique for financial support and Professor L. Ouahab (University of Rennes-1, France) for helpful discussions.

References

Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Mirkhani, V., Moghadam, M., Tanjestaminejad, S. & Bahramian, B. (2006). Appl. Catal. A, 311, 43–50. CrossRef CAS Google Scholar
Moutet, J. C. & Ourari, A. (1997). Electrochim. Acta, 42, 2525–2531. CrossRef CAS Web of Science Google Scholar
Ourari, A., Ouari, K., Khan, M. A. & Bouet, G. (2008). J. Coord. Chem. 61, 3846–3859. Web of Science CrossRef CAS Google Scholar
Ourari, A., Ouari, K., Moumeni, W., Sibous, L., Bouet, G. & Khan, M. A. (2006). Transition Met. Chem. 31, 169–175. Web of Science CrossRef CAS Google Scholar
Oyaizu, K., Nakagawa, T. & Tsuchida, E. (2000). Inorg. Chim. Acta, 305, 184–188. Web of Science CSD CrossRef CAS Google Scholar
Salomao, G. C., Olsen, M. H. N., Drago, V., Fernandes, C., Filho, L. C. & Atunes, O. A. C. (2007). Catal. Commun. 8, 69–72. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Srinivasan, K., Michaud, P. J. & Kochi, K. (1986). J. Am. Chem. Soc. 108, 2309–2320. CSD CrossRef CAS PubMed Web of Science Google Scholar
Trivedi, B. M., Bhattacharya, P. K., Ganeshpure, P. A. & Satish, S. (1992). J. Mol. Catal. A, 75, 109–115. CrossRef CAS Web of Science Google Scholar
Zhang, X., Wei, P., Li, B., Wu, C. & Hu, B. (2009). Acta Cryst. E65, m707. Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.