Aqua­azido­{3,3′-[o-phenyl­enebis(nitrilo­methyl­idyne)]di-2-naphtholato}manganese(III)

Wang, C.-J.; Zhou, X.-L.; Zhang, B.-J.

doi:10.1107/S1600536809052659

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page m50

doi:10.1107/S1600536809052659

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Aquaazido{3,3′-[o-phenylenebis(nitrilomethylidyne)]di-2-naphtholato}manganese(III)

Cui-Juan Wang,^a ^* Xian-Li Zhou ^a and Bing-Jun Zhang ^a

^aDepartment of Chemistry and Chemical Engineering, School of Bioengineering, SouthWest JiaoTong University, Chengdu, Sichuan 610031, People's Republic of China
^*Correspondence e-mail: wangcuijuan2000@126.com

(Received 2 December 2009; accepted 8 December 2009; online 12 December 2009)

In the title complex, [Mn(C₂₈H₁₈N₂O₂)(N₃)(H₂O)], the Mn^III ion adopts a distorted fac-MnO₃N₃ octahedral geometry arising from the O,N,N′,O′-tetradentate Schiff base ligand, an azide ion and a water molecule. In the crystal, intermolecular O—H⋯(O,O) and O—H⋯N hydrogen bonds and π–π interactions [centroid–centroid separation = 3.5535 (13) Å] link the molecules into chains.

Related literature

For background to Schiff base–metal complexes, see: Sunatsuki et al. (2002 ).

Experimental

Crystal data

[Mn(C₂₈H₁₈N₂O₂)(N₃)(H₂O)]
M_r = 529.43
Triclinic, $[P \overline 1]$
a = 6.6827 (1) Å
b = 11.8803 (2) Å
c = 15.3778 (3) Å
α = 99.455 (1)°
β = 97.692 (1)°
γ = 98.180 (1)°
V = 1176.49 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.60 mm⁻¹
T = 298 K
0.29 × 0.20 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.844, T_max = 0.931
12984 measured reflections
4205 independent reflections
3519 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.121
S = 0.88
4205 reflections
340 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Selected bond lengths (Å)

Mn1—O2	1.8644 (15)
Mn1—O1	1.8799 (14)
Mn1—N1	1.9663 (17)
Mn1—N2	1.9672 (17)
Mn1—N3	2.2465 (19)
Mn1—O3	2.3905 (16)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3WA⋯N3ⁱ	0.82 (1)	2.10 (3)	2.911 (3)	167 (4)
O3—H3WB⋯O1ⁱⁱ	0.82 (3)	2.14 (3)	2.941 (2)	164 (4)
O3—H3WB⋯O2ⁱⁱ	0.82 (3)	2.57 (3)	3.130 (2)	127 (3)
Symmetry codes: (i) x-1, y, z; (ii) -x, -y, -z+2.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809052659/hb5265sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809052659/hb5265Isup2.hkl

checkCIF report

Comment top

In recent years, there has been considerable interest in the chemistry of transition metal complexes of Schiff bases (Sunatsuki et al., 2002). In this paper, we report here the synthesis and crystal structure of the title complex (I).

The molecular structure of (I) is illustrated in Fig. 1. The Mn^III ion takes a slightly distorted octahedral geometry, where the equatorial plane comprise the two N atoms two imine nitrogen atoms and two O atoms of alkoxide groups. The apical postiions are occupied by the N atom of azide ligand and one O atom from water molecule. The Mn—N(azide) bond length is significantly longer than the Mn-N(imine) (Table 1) and the bond angles deviate from the ideal values (the largest angle is 173.80 (7)°). The chelate bite angles in the five-membered and the six-membered rings formed by the coordination of alkoxide-O and imine-N, and two related imine-N of Schiff base to the Mn^III center lie in same plane and are almost parallel to the naphthalen rings with 2.6°.

The structure is further stabilized by strongly π-π stacking interactions between two adjacent naphthalen rings in an offset arrangement. The distance between the centroids of the six-membered rings is 3.55 (3)Å. In addition, Intermolecular O-H···O, O-H···N hydrogen bonds form a zig-zag like chain parallel to the b axis (Table 2).

Related literature top

For background to Schiff base–metal complexes, see: Sunatsuki et al. (2002).

Experimental top

A mixture of Mn(Ac)₃, NaN₃ and 3-((1E)-((E)-2-((naphthalen-2-yl)methyleneamino) phenylimino)methyl)naphthalen-2,2'-diol in water (30mL) was refluxed for 5 hours and then filtered while hot. Colourless blocks of (I) were obtained by evaporating the filtrate at room temperature for a period of three weeks. The compound is insoluble in commom organic solvents and dissolves water very slowly.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. Molecular view of (I) with ellipsoids drawn at the the 30% probability level. H atoms are shown as spheres of arbitrary radius.

Aquaazido{3,3'-[o-phenylenebis(nitrilomethylidyne)]di-2- naphtholato}manganese(III) top

Crystal data top

[Mn(C₂₈H₁₈N₂O₂)(N₃)(H₂O)]	Z = 2
M_r = 529.43	F(000) = 544
Triclinic, P1	D_x = 1.495 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.6827 (1) Å	Cell parameters from 4205 reflections
b = 11.8803 (2) Å	θ = 2.2–25.2°
c = 15.3778 (3) Å	µ = 0.60 mm⁻¹
α = 99.455 (1)°	T = 298 K
β = 97.692 (1)°	Block, colourless
γ = 98.180 (1)°	0.29 × 0.20 × 0.12 mm
V = 1176.49 (4) Å³

Data collection top

Bruker APEXII CCD diffractometer	4205 independent reflections
Radiation source: fine-focus sealed tube	3519 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scan	θ_max = 25.2°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→8
T_min = 0.844, T_max = 0.931	k = −14→13
12984 measured reflections	l = −18→18

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 0.88	w = 1/[σ²(F_o²) + (0.1P)² + 0.1339P] where P = (F_o² + 2F_c²)/3
4205 reflections	(Δ/σ)_max = 0.001
340 parameters	Δρ_max = 0.26 e Å⁻³
3 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

[Mn(C₂₈H₁₈N₂O₂)(N₃)(H₂O)]	γ = 98.180 (1)°
M_r = 529.43	V = 1176.49 (4) Å³
Triclinic, P1	Z = 2
a = 6.6827 (1) Å	Mo Kα radiation
b = 11.8803 (2) Å	µ = 0.60 mm⁻¹
c = 15.3778 (3) Å	T = 298 K
α = 99.455 (1)°	0.29 × 0.20 × 0.12 mm
β = 97.692 (1)°

Data collection top

Bruker APEXII CCD diffractometer	4205 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3519 reflections with I > 2σ(I)
T_min = 0.844, T_max = 0.931	R_int = 0.025
12984 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	3 restraints
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 0.88	Δρ_max = 0.26 e Å⁻³
4205 reflections	Δρ_min = −0.23 e Å⁻³
340 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.21230 (5)	0.16035 (2)	0.939323 (19)	0.03163 (14)
N2	0.2571 (3)	0.32332 (14)	0.99968 (12)	0.0311 (4)
O1	0.1336 (2)	0.00645 (12)	0.87811 (10)	0.0356 (4)
N1	0.0823 (3)	0.22059 (14)	0.83821 (12)	0.0307 (4)
O2	0.3187 (2)	0.11226 (12)	1.04281 (10)	0.0378 (4)
C11	0.0019 (3)	0.15759 (19)	0.76023 (15)	0.0337 (5)
H11	−0.0463	0.1971	0.7165	0.040*
O3	−0.1107 (2)	0.14771 (13)	0.99088 (12)	0.0411 (4)
C1	0.0450 (3)	−0.03427 (17)	0.79550 (14)	0.0303 (5)
C28	0.3879 (3)	0.17238 (18)	1.12325 (14)	0.0322 (5)
C19	0.3971 (3)	0.29292 (19)	1.14745 (14)	0.0339 (5)
C10	−0.0201 (3)	0.03561 (18)	0.73472 (14)	0.0317 (5)
C16	0.2261 (4)	0.51867 (18)	0.96493 (16)	0.0396 (5)
H16	0.2947	0.5559	1.0212	0.048*
C18	0.3317 (3)	0.36058 (18)	1.08433 (15)	0.0335 (5)
H18	0.3430	0.4396	1.1054	0.040*
N3	0.5156 (3)	0.19321 (18)	0.89218 (13)	0.0432 (5)
C22	0.5792 (5)	0.5194 (3)	1.35685 (19)	0.0701 (9)
H22	0.5873	0.5986	1.3757	0.084*
C25	0.5511 (4)	0.2830 (2)	1.30092 (16)	0.0426 (6)
C12	0.0973 (3)	0.34341 (17)	0.85631 (15)	0.0340 (5)
C9	−0.1130 (3)	−0.0194 (2)	0.64364 (15)	0.0369 (5)
C4	−0.1307 (3)	−0.1403 (2)	0.61810 (15)	0.0401 (5)
C5	−0.2167 (4)	−0.1956 (2)	0.52954 (17)	0.0526 (7)
H5	−0.2277	−0.2754	0.5134	0.063*
C3	−0.0665 (3)	−0.20654 (19)	0.68215 (15)	0.0391 (5)
H3	−0.0817	−0.2865	0.6652	0.047*
C2	0.0163 (3)	−0.15628 (18)	0.76743 (14)	0.0341 (5)
H2	0.0549	−0.2023	0.8081	0.041*
C21	0.4955 (4)	0.4698 (2)	1.27051 (18)	0.0534 (7)
H21	0.4480	0.5161	1.2318	0.064*
C20	0.4797 (3)	0.3504 (2)	1.23912 (15)	0.0388 (5)
C6	−0.2835 (4)	−0.1338 (3)	0.46767 (18)	0.0615 (8)
H6	−0.3387	−0.1706	0.4095	0.074*
C14	0.0525 (4)	0.5279 (2)	0.82062 (18)	0.0484 (6)
H14	0.0026	0.5718	0.7804	0.058*
C15	0.1542 (4)	0.58246 (19)	0.90428 (17)	0.0435 (6)
H15	0.1742	0.6628	0.9197	0.052*
C26	0.5337 (4)	0.1611 (2)	1.27266 (16)	0.0429 (6)
H26	0.5778	0.1170	1.3138	0.051*
C13	0.0239 (4)	0.4089 (2)	0.79603 (17)	0.0453 (6)
H13	−0.0441	0.3728	0.7394	0.054*
C17	0.1963 (3)	0.39877 (17)	0.94229 (14)	0.0323 (5)
C8	−0.1867 (4)	0.0416 (2)	0.57819 (17)	0.0507 (6)
H8	−0.1800	0.1213	0.5932	0.061*
C27	0.4558 (3)	0.1080 (2)	1.18858 (15)	0.0383 (5)
H27	0.4460	0.0282	1.1727	0.046*
C24	0.6383 (4)	0.3370 (3)	1.38941 (17)	0.0570 (7)
H24	0.6868	0.2925	1.4294	0.068*
C7	−0.2677 (4)	−0.0144 (3)	0.49312 (17)	0.0589 (7)
H7	−0.3134	0.0283	0.4512	0.071*
C23	0.6525 (5)	0.4530 (3)	1.41707 (19)	0.0712 (9)
H23	0.7105	0.4877	1.4754	0.085*
N4	0.5327 (3)	0.21532 (17)	0.82123 (15)	0.0454 (5)
N5	0.5512 (4)	0.2366 (3)	0.75124 (19)	0.0928 (10)
H3WA	−0.218 (3)	0.149 (3)	0.958 (2)	0.139*
H3WB	−0.129 (6)	0.095 (3)	1.019 (2)	0.139*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0397 (2)	0.0212 (2)	0.0312 (2)	0.00640 (14)	−0.00187 (14)	0.00203 (13)
N2	0.0304 (9)	0.0229 (8)	0.0391 (10)	0.0044 (7)	0.0049 (8)	0.0039 (7)
O1	0.0485 (9)	0.0231 (7)	0.0323 (8)	0.0081 (6)	−0.0029 (7)	0.0024 (6)
N1	0.0336 (9)	0.0223 (9)	0.0356 (10)	0.0045 (7)	0.0035 (8)	0.0052 (7)
O2	0.0491 (9)	0.0282 (8)	0.0333 (8)	0.0083 (7)	−0.0016 (7)	0.0030 (6)
C11	0.0342 (11)	0.0340 (12)	0.0343 (12)	0.0075 (9)	0.0026 (9)	0.0108 (9)
O3	0.0420 (9)	0.0340 (9)	0.0492 (10)	0.0069 (7)	0.0057 (7)	0.0137 (7)
C1	0.0284 (10)	0.0281 (10)	0.0324 (11)	0.0036 (8)	0.0045 (9)	0.0014 (9)
C28	0.0279 (10)	0.0342 (12)	0.0331 (11)	0.0046 (8)	0.0046 (9)	0.0034 (9)
C19	0.0314 (11)	0.0334 (12)	0.0343 (12)	0.0018 (9)	0.0054 (9)	0.0022 (9)
C10	0.0313 (11)	0.0308 (11)	0.0311 (11)	0.0040 (8)	0.0024 (9)	0.0033 (9)
C16	0.0421 (12)	0.0278 (11)	0.0495 (14)	0.0055 (9)	0.0125 (11)	0.0049 (10)
C18	0.0308 (11)	0.0266 (10)	0.0399 (12)	0.0016 (8)	0.0075 (9)	−0.0015 (9)
N3	0.0398 (11)	0.0522 (12)	0.0410 (12)	0.0148 (9)	0.0072 (9)	0.0120 (9)
C22	0.092 (2)	0.0518 (17)	0.0509 (17)	0.0014 (16)	0.0000 (16)	−0.0164 (14)
C25	0.0356 (12)	0.0539 (15)	0.0356 (12)	0.0069 (10)	0.0064 (10)	0.0006 (11)
C12	0.0337 (11)	0.0262 (11)	0.0441 (13)	0.0062 (9)	0.0080 (10)	0.0096 (9)
C9	0.0358 (12)	0.0392 (12)	0.0330 (12)	0.0037 (9)	0.0025 (9)	0.0040 (9)
C4	0.0384 (12)	0.0417 (13)	0.0355 (12)	0.0007 (10)	0.0052 (10)	−0.0010 (10)
C5	0.0602 (16)	0.0482 (15)	0.0389 (14)	−0.0036 (12)	0.0011 (12)	−0.0052 (12)
C3	0.0425 (13)	0.0270 (11)	0.0426 (13)	0.0019 (9)	0.0033 (10)	−0.0024 (9)
C2	0.0370 (11)	0.0276 (11)	0.0368 (12)	0.0055 (9)	0.0034 (9)	0.0052 (9)
C21	0.0634 (17)	0.0437 (14)	0.0456 (15)	0.0030 (12)	0.0044 (13)	−0.0050 (12)
C20	0.0351 (12)	0.0410 (13)	0.0363 (12)	0.0014 (10)	0.0071 (10)	−0.0014 (10)
C6	0.0670 (18)	0.0696 (19)	0.0353 (14)	−0.0041 (15)	−0.0060 (13)	−0.0019 (13)
C14	0.0572 (15)	0.0338 (13)	0.0608 (16)	0.0148 (11)	0.0081 (13)	0.0226 (12)
C15	0.0487 (14)	0.0228 (11)	0.0625 (16)	0.0077 (10)	0.0170 (12)	0.0100 (11)
C26	0.0409 (13)	0.0531 (14)	0.0370 (13)	0.0148 (11)	0.0017 (10)	0.0127 (11)
C13	0.0532 (14)	0.0327 (12)	0.0490 (14)	0.0093 (10)	0.0009 (11)	0.0092 (11)
C17	0.0300 (10)	0.0259 (10)	0.0420 (12)	0.0033 (8)	0.0101 (9)	0.0069 (9)
C8	0.0578 (15)	0.0496 (15)	0.0413 (14)	0.0081 (12)	−0.0041 (12)	0.0095 (11)
C27	0.0367 (12)	0.0392 (12)	0.0399 (13)	0.0114 (9)	0.0024 (10)	0.0087 (10)
C24	0.0590 (17)	0.0692 (19)	0.0370 (14)	0.0096 (14)	−0.0001 (12)	0.0011 (13)
C7	0.0646 (17)	0.0703 (19)	0.0391 (14)	0.0113 (14)	−0.0051 (13)	0.0133 (13)
C23	0.086 (2)	0.073 (2)	0.0393 (15)	0.0053 (17)	−0.0039 (15)	−0.0150 (14)
N4	0.0364 (11)	0.0474 (12)	0.0519 (13)	0.0075 (9)	0.0045 (9)	0.0099 (10)
N5	0.0725 (18)	0.149 (3)	0.0665 (18)	0.0116 (18)	0.0128 (15)	0.0513 (19)

Geometric parameters (Å, º) top

Mn1—O2	1.8644 (15)	C25—C20	1.417 (3)
Mn1—O1	1.8799 (14)	C25—C26	1.425 (4)
Mn1—N1	1.9663 (17)	C12—C13	1.389 (3)
Mn1—N2	1.9672 (17)	C12—C17	1.405 (3)
Mn1—N3	2.2465 (19)	C9—C4	1.409 (3)
Mn1—O3	2.3905 (16)	C9—C8	1.411 (3)
N2—C18	1.309 (3)	C4—C5	1.416 (3)
N2—C17	1.419 (3)	C4—C3	1.418 (3)
O1—C1	1.309 (2)	C5—C6	1.361 (4)
N1—C11	1.306 (3)	C5—H5	0.9300
N1—C12	1.426 (3)	C3—C2	1.355 (3)
O2—C28	1.310 (3)	C3—H3	0.9300
C11—C10	1.419 (3)	C2—H2	0.9300
C11—H11	0.9300	C21—C20	1.405 (3)
O3—H3WA	0.824 (10)	C21—H21	0.9300
O3—H3WB	0.82 (3)	C6—C7	1.393 (4)
C1—C10	1.414 (3)	C6—H6	0.9300
C1—C2	1.420 (3)	C14—C15	1.380 (4)
C28—C19	1.409 (3)	C14—C13	1.381 (3)
C28—C27	1.425 (3)	C14—H14	0.9300
C19—C18	1.422 (3)	C15—H15	0.9300
C19—C20	1.458 (3)	C26—C27	1.341 (3)
C10—C9	1.458 (3)	C26—H26	0.9300
C16—C15	1.375 (3)	C13—H13	0.9300
C16—C17	1.388 (3)	C8—C7	1.367 (4)
C16—H16	0.9300	C8—H8	0.9300
C18—H18	0.9300	C27—H27	0.9300
N3—N4	1.180 (3)	C24—C23	1.359 (4)
C22—C21	1.369 (4)	C24—H24	0.9300
C22—C23	1.396 (4)	C7—H7	0.9300
C22—H22	0.9300	C23—H23	0.9300
C25—C24	1.413 (3)	N4—N5	1.163 (3)

O2—Mn1—O1	91.53 (6)	C17—C12—N1	115.35 (18)
O2—Mn1—N1	173.78 (7)	C4—C9—C8	117.2 (2)
O1—Mn1—N1	92.11 (7)	C4—C9—C10	119.0 (2)
O2—Mn1—N2	92.48 (7)	C8—C9—C10	123.8 (2)
O1—Mn1—N2	172.58 (6)	C9—C4—C5	120.2 (2)
N1—Mn1—N2	83.37 (7)	C9—C4—C3	119.6 (2)
O2—Mn1—N3	94.70 (7)	C5—C4—C3	120.2 (2)
O1—Mn1—N3	96.71 (7)	C6—C5—C4	121.1 (3)
N1—Mn1—N3	89.87 (7)	C6—C5—H5	119.5
N2—Mn1—N3	89.18 (7)	C4—C5—H5	119.5
O2—Mn1—O3	88.06 (6)	C2—C3—C4	121.7 (2)
O1—Mn1—O3	88.87 (6)	C2—C3—H3	119.2
N1—Mn1—O3	86.98 (6)	C4—C3—H3	119.2
N2—Mn1—O3	85.04 (6)	C3—C2—C1	120.8 (2)
N3—Mn1—O3	173.70 (6)	C3—C2—H2	119.6
C18—N2—C17	122.21 (18)	C1—C2—H2	119.6
C18—N2—Mn1	124.62 (15)	C22—C21—C20	121.4 (3)
C17—N2—Mn1	113.16 (13)	C22—C21—H21	119.3
C1—O1—Mn1	129.97 (13)	C20—C21—H21	119.3
C11—N1—C12	122.49 (18)	C21—C20—C25	117.3 (2)
C11—N1—Mn1	124.55 (15)	C21—C20—C19	124.1 (2)
C12—N1—Mn1	112.82 (14)	C25—C20—C19	118.7 (2)
C28—O2—Mn1	129.92 (14)	C5—C6—C7	118.8 (2)
N1—C11—C10	127.3 (2)	C5—C6—H6	120.6
N1—C11—H11	116.4	C7—C6—H6	120.6
C10—C11—H11	116.4	C15—C14—C13	120.7 (2)
Mn1—O3—H3WA	122 (3)	C15—C14—H14	119.7
Mn1—O3—H3WB	112 (3)	C13—C14—H14	119.7
H3WA—O3—H3WB	109 (2)	C16—C15—C14	120.3 (2)
O1—C1—C10	123.96 (18)	C16—C15—H15	119.8
O1—C1—C2	116.30 (18)	C14—C15—H15	119.8
C10—C1—C2	119.74 (18)	C27—C26—C25	122.1 (2)
O2—C28—C19	124.40 (19)	C27—C26—H26	119.0
O2—C28—C27	115.74 (19)	C25—C26—H26	119.0
C19—C28—C27	119.9 (2)	C14—C13—C12	119.7 (2)
C28—C19—C18	121.72 (19)	C14—C13—H13	120.2
C28—C19—C20	119.3 (2)	C12—C13—H13	120.2
C18—C19—C20	119.0 (2)	C16—C17—C12	119.6 (2)
C1—C10—C11	121.72 (19)	C16—C17—N2	125.5 (2)
C1—C10—C9	119.03 (19)	C12—C17—N2	114.96 (17)
C11—C10—C9	119.25 (19)	C7—C8—C9	121.1 (2)
C15—C16—C17	120.1 (2)	C7—C8—H8	119.4
C15—C16—H16	120.0	C9—C8—H8	119.4
C17—C16—H16	120.0	C26—C27—C28	120.8 (2)
N2—C18—C19	126.8 (2)	C26—C27—H27	119.6
N2—C18—H18	116.6	C28—C27—H27	119.6
C19—C18—H18	116.6	C23—C24—C25	121.1 (3)
N4—N3—Mn1	123.20 (16)	C23—C24—H24	119.5
C21—C22—C23	121.1 (3)	C25—C24—H24	119.5
C21—C22—H22	119.5	C8—C7—C6	121.6 (3)
C23—C22—H22	119.5	C8—C7—H7	119.2
C24—C25—C20	119.9 (2)	C6—C7—H7	119.2
C24—C25—C26	120.8 (2)	C24—C23—C22	119.2 (3)
C20—C25—C26	119.3 (2)	C24—C23—H23	120.4
C13—C12—C17	119.66 (19)	C22—C23—H23	120.4
C13—C12—N1	125.0 (2)	N5—N4—N3	179.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3WA···N3ⁱ	0.82 (1)	2.10 (3)	2.911 (3)	167 (4)
O3—H3WB···O1ⁱⁱ	0.82 (3)	2.14 (3)	2.941 (2)	164 (4)
O3—H3WB···O2ⁱⁱ	0.82 (3)	2.57 (3)	3.130 (2)	127 (3)

Symmetry codes: (i) x−1, y, z; (ii) −x, −y, −z+2.

Experimental details

Crystal data
Chemical formula	[Mn(C₂₈H₁₈N₂O₂)(N₃)(H₂O)]
M_r	529.43
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	6.6827 (1), 11.8803 (2), 15.3778 (3)
α, β, γ (°)	99.455 (1), 97.692 (1), 98.180 (1)
V (Å³)	1176.49 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.60
Crystal size (mm)	0.29 × 0.20 × 0.12

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.844, 0.931
No. of measured, independent and observed [I > 2σ(I)] reflections	12984, 4205, 3519
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.121, 0.88
No. of reflections	4205
No. of parameters	340
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.23

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2009).

Selected bond lengths (Å) top

Mn1—O2	1.8644 (15)	Mn1—N2	1.9672 (17)
Mn1—O1	1.8799 (14)	Mn1—N3	2.2465 (19)
Mn1—N1	1.9663 (17)	Mn1—O3	2.3905 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3WA···N3ⁱ	0.824 (10)	2.10 (3)	2.911 (3)	167 (4)
O3—H3WB···O1ⁱⁱ	0.82 (3)	2.14 (3)	2.941 (2)	164 (4)
O3—H3WB···O2ⁱⁱ	0.82 (3)	2.57 (3)	3.130 (2)	127 (3)

Symmetry codes: (i) x−1, y, z; (ii) −x, −y, −z+2.

Acknowledgements

This work was supported by the Science and Technology Development Fund of SouthWest JiaoTong University

References

Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sunatsuki, Y., Motoda, Y. & Matsumoto, N. (2002). Coord. Chem. Rev. 226, 199–209. Web of Science CrossRef CAS Google Scholar

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Volume 66| Part 1| January 2010| Page m50

doi:10.1107/S1600536809052659

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Aqua­azido­{3,3′-[o-phenyl­enebis(nitrilo­methyl­­idyne)]di-2-naphtholato}manganese(III)

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Aquaazido{3,3′-[o-phenylenebis(nitrilomethylidyne)]di-2-naphtholato}manganese(III)