Bis[N′-(2-oxo-1H-indol-3-ylidene)furan-2-carbohydrazidato-κ3O,N′,O′]manganese(II) N,N-dimethyl­formide monosolvate monohydrate

Abdul Halim, S.N.; Ali, H.M.; Ng, S.W.

doi:10.1107/S1600536810039516

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page m1439

https://doi.org/10.1107/S1600536810039516

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Bis[N′-(2-oxo-1H-indol-3-ylidene)furan-2-carbohydrazidato-κ³O,N′,O′]manganese(II) N,N-dimethylformide monosolvate monohydrate

Siti Nadiah Abdul Halim,^a ^* Hapipah Mohd Ali ^a and Seik Weng Ng ^a

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: nadiahhalim@um.edu.my

(Received 19 August 2010; accepted 4 October 2010; online 23 October 2010)

In the title compound, [Mn(C₁₃H₈N₃O₃)₂]·C₃H₇NO·H₂O, the metal atom is O,N,O′-chelated by two deprotonated Schiff bases and exists in a distorted octahedral geometry. The N–H groups, the carbonyl group of the DMF molecule and the uncoordinated water molecule engage in N—H⋯O and O—H⋯O hydrogen-bonding interactions, generating a hydrogen-bonded ribbon that propagates along [110].

Related literature

For the crystal structure of the uncoordinated Schiff base ligand, see: Rodríguez-Argüelles et al. (2009 ).

Experimental

Crystal data

[Mn(C₁₃H₈N₃O₃)₂]·C₃H₇NO·H₂O
M_r = 654.50
Triclinic, $[P \overline 1]$
a = 11.4833 (7) Å
b = 11.5599 (7) Å
c = 13.1619 (8) Å
α = 107.580 (1)°
β = 97.800 (1)°
γ = 115.159 (1)°
V = 1435.21 (15) Å³
Z = 2
Mo Kα radiation
μ = 0.53 mm⁻¹
T = 295 K
0.45 × 0.32 × 0.20 mm

Data collection

Bruker SMART area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.798, T_max = 0.902
12170 measured reflections
6180 independent reflections
4297 reflections with I > 2I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.126
S = 0.95
6180 reflections
420 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.61 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Selected bond lengths (Å)

Mn1—N2	2.016 (2)
Mn1—N5	2.023 (2)
Mn1—O5	2.0667 (18)
Mn1—O2	2.076 (2)
Mn1—O3	2.2676 (19)
Mn1—O6	2.2998 (19)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯O3	0.86 (1)	2.06 (2)	2.896 (3)	165 (4)
O1W—H1W2⋯O7	0.86 (1)	1.93 (2)	2.762 (5)	161 (4)
N3—H3⋯O1Wⁱ	0.86 (1)	1.96 (1)	2.811 (4)	176 (3)
N6—H6⋯O6ⁱⁱ	0.87 (1)	2.05 (1)	2.899 (3)	167 (3)
Symmetry codes: (i) -x, -y, -z+1; (ii) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810039516/ci5164sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810039516/ci5164Isup2.hkl

checkCIF report

Comment top

Divalent cobalt, nickel, copper and zinc derivatives of Schiff base condensation product of isatin and 2-furoic acid hydrazide have been synthesized, and these are reported along with the crystal structure of the Schiff base (Rodríguez-Argüelles et al., 2009). If the deprotonated Schiff base is to chelate in a terdentate manner, the anion has to rotate about the nitrogen-nitrogen bond. Such a rotation is observed in the manganese derivative, which crystallizes from DMF as a monohydrated monosolvate (Scheme I). The divalent metal atom is O,N,O'-chelated by two deprotonated Schiff base in an octahedral geometry (Fig. 1). The amino group, the carbonyl group of the DMF and the lattice water molecule engage in N—H···O and O—H···O hydrogen bonding interactions to generate a hydrogen-bonded ribbon that propagates along [110].

Related literature top

For the crystal structure of the uncoordinated Schiff base ligand, see: Rodríguez-Argüelles et al. (2009).

Experimental top

The Schiff base was synthesized by condensing isatin and furoylhydrazine according to a literature procedure (Rodríguez-Argüelles et al., 2009). Manganese acetate (1 mmol) and the Schiff base (2 mmol) were heated in ethanol (100 ml) for 5 h; several drops of triethylamine were added. The solvent was removed and the product purified by recrystallization from DMF.

Structure description top

For the crystal structure of the uncoordinated Schiff base ligand, see: Rodríguez-Argüelles et al. (2009).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as spheres of arbitrary radius.

Bis[N'-(2-oxo-1H-indol-3-ylidene)furan-2-carbohydrazidato- κ³O,N',O']manganese(II) N,N-dimethylformide monosolvate monohydrate top

Crystal data top

[Mn(C₁₃H₈N₃O₃)₂]·C₃H₇NO·H₂O	Z = 2
M_r = 654.50	F(000) = 674
Triclinic, P1	D_x = 1.515 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.4833 (7) Å	Cell parameters from 4583 reflections
b = 11.5599 (7) Å	θ = 2.2–26.7°
c = 13.1619 (8) Å	µ = 0.53 mm⁻¹
α = 107.580 (1)°	T = 295 K
β = 97.800 (1)°	Block, black
γ = 115.159 (1)°	0.45 × 0.32 × 0.20 mm
V = 1435.21 (15) Å³

Data collection top

Bruker SMART area-detector diffractometer	6180 independent reflections
Radiation source: fine-focus sealed tube	4297 reflections with I > 2˘I)
Graphite monochromator	R_int = 0.019
ω scans	θ_max = 27.1°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
T_min = 0.798, T_max = 0.902	k = −14→14
12170 measured reflections	l = −16→16

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	w = 1/[σ²(F_o²) + (0.0671P)² + 0.6988P] where P = (F_o² + 2F_c²)/3
6180 reflections	(Δ/σ)_max = 0.001
420 parameters	Δρ_max = 0.61 e Å⁻³
4 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

[Mn(C₁₃H₈N₃O₃)₂]·C₃H₇NO·H₂O	γ = 115.159 (1)°
M_r = 654.50	V = 1435.21 (15) Å³
Triclinic, P1	Z = 2
a = 11.4833 (7) Å	Mo Kα radiation
b = 11.5599 (7) Å	µ = 0.53 mm⁻¹
c = 13.1619 (8) Å	T = 295 K
α = 107.580 (1)°	0.45 × 0.32 × 0.20 mm
β = 97.800 (1)°

Data collection top

Bruker SMART area-detector diffractometer	6180 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4297 reflections with I > 2˘I)
T_min = 0.798, T_max = 0.902	R_int = 0.019
12170 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	4 restraints
wR(F²) = 0.126	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	Δρ_max = 0.61 e Å⁻³
6180 reflections	Δρ_min = −0.26 e Å⁻³
420 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.

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

	x	y	z	U_iso*/U_eq
Mn1	0.48864 (4)	0.33824 (4)	0.74033 (3)	0.03787 (13)
O1	0.8779 (2)	0.7680 (2)	0.9910 (2)	0.0715 (6)
O2	0.66584 (18)	0.5205 (2)	0.84440 (17)	0.0580 (5)
O3	0.26092 (19)	0.2002 (2)	0.67083 (16)	0.0536 (5)
O4	0.5776 (2)	0.0564 (2)	0.90415 (16)	0.0584 (5)
O5	0.51399 (19)	0.21270 (19)	0.81422 (15)	0.0510 (5)
O6	0.4817 (2)	0.4103 (2)	0.59584 (16)	0.0565 (5)
O7	0.2100 (4)	0.2105 (4)	0.3397 (3)	0.1265 (12)
O1W	0.1448 (3)	0.0178 (3)	0.4351 (2)	0.0872 (8)
H1W1	0.168 (4)	0.059 (4)	0.5069 (9)	0.105*
H1W2	0.153 (4)	0.084 (3)	0.413 (3)	0.105*
N1	0.5167 (2)	0.5882 (2)	0.90994 (18)	0.0448 (5)
N2	0.4257 (2)	0.4610 (2)	0.83192 (18)	0.0429 (5)
N3	0.0846 (2)	0.2401 (3)	0.7046 (2)	0.0530 (6)
H3	0.017 (2)	0.1608 (18)	0.660 (2)	0.064*
N4	0.6060 (2)	0.1576 (2)	0.67171 (17)	0.0406 (5)
N5	0.5641 (2)	0.2372 (2)	0.64017 (17)	0.0406 (5)
N6	0.5591 (2)	0.3727 (3)	0.4406 (2)	0.0527 (6)
H6	0.544 (3)	0.430 (3)	0.418 (2)	0.063*
N7	0.1231 (3)	0.3539 (4)	0.3902 (3)	0.0870 (10)
C1	0.9606 (4)	0.8932 (4)	1.0792 (3)	0.0838 (11)
H1	1.0543	0.9406	1.0972	0.101*
C2	0.8913 (4)	0.9391 (4)	1.1360 (3)	0.0743 (10)
H2	0.9261	1.0217	1.1989	0.089*
C3	0.7542 (3)	0.8375 (3)	1.0817 (2)	0.0543 (7)
H3A	0.6805	0.8401	1.1019	0.065*
C4	0.7501 (3)	0.7363 (3)	0.9952 (2)	0.0473 (6)
C5	0.6409 (3)	0.6055 (3)	0.9102 (2)	0.0425 (6)
C6	0.2148 (3)	0.2725 (3)	0.7204 (2)	0.0456 (6)
C7	0.2962 (2)	0.4144 (3)	0.8083 (2)	0.0421 (6)
C8	0.2058 (3)	0.4627 (3)	0.8430 (2)	0.0447 (6)
C9	0.2232 (3)	0.5855 (3)	0.9194 (2)	0.0553 (7)
H9	0.3090	0.6589	0.9636	0.066*
C10	0.1083 (4)	0.5958 (4)	0.9281 (3)	0.0682 (9)
H10	0.1169	0.6778	0.9779	0.082*
C11	−0.0186 (3)	0.4850 (4)	0.8634 (3)	0.0709 (9)
H11	−0.0939	0.4938	0.8718	0.085*
C12	−0.0379 (3)	0.3611 (4)	0.7864 (3)	0.0623 (8)
H12	−0.1239	0.2875	0.7430	0.075*
C13	0.0758 (3)	0.3521 (3)	0.7773 (2)	0.0487 (6)
C14	0.6181 (3)	−0.0311 (4)	0.9250 (3)	0.0682 (9)
H14	0.6078	−0.0587	0.9841	0.082*
C15	0.6745 (3)	−0.0724 (3)	0.8495 (3)	0.0627 (8)
H15	0.7100	−0.1317	0.8469	0.075*
C16	0.6695 (3)	−0.0079 (3)	0.7746 (3)	0.0524 (7)
H16	0.7009	−0.0168	0.7127	0.063*
C17	0.6104 (3)	0.0691 (3)	0.8102 (2)	0.0441 (6)
C18	0.5727 (2)	0.1531 (3)	0.7664 (2)	0.0397 (5)
C19	0.5330 (3)	0.3554 (3)	0.5333 (2)	0.0459 (6)
C20	0.5793 (2)	0.2607 (3)	0.5509 (2)	0.0422 (6)
C21	0.6341 (2)	0.2229 (3)	0.4619 (2)	0.0436 (6)
C22	0.6909 (3)	0.1385 (3)	0.4341 (2)	0.0526 (7)
H22	0.7013	0.0916	0.4779	0.063*
C23	0.7322 (3)	0.1256 (3)	0.3391 (3)	0.0636 (8)
H23	0.7696	0.0683	0.3182	0.076*
C24	0.7183 (3)	0.1973 (3)	0.2746 (3)	0.0660 (9)
H24	0.7475	0.1876	0.2116	0.079*
C25	0.6621 (3)	0.2828 (3)	0.3020 (2)	0.0600 (8)
H25	0.6531	0.3307	0.2588	0.072*
C26	0.6202 (3)	0.2940 (3)	0.3953 (2)	0.0479 (6)
C27	0.1768 (6)	0.2935 (6)	0.3242 (4)	0.121 (2)
H27	0.1900	0.3152	0.2627	0.145*
C28	0.1071 (5)	0.3253 (5)	0.4865 (4)	0.1004 (13)
H28A	0.1883	0.3317	0.5249	0.151*
H28B	0.0329	0.2329	0.4643	0.151*
H28C	0.0892	0.3919	0.5356	0.151*
C29	0.0825 (5)	0.4465 (6)	0.3654 (6)	0.167 (3)
H29A	0.1070	0.4600	0.3013	0.251*
H29B	0.1269	0.5348	0.4286	0.251*
H29C	−0.0137	0.4067	0.3498	0.251*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0398 (2)	0.0382 (2)	0.0430 (2)	0.02413 (17)	0.01540 (16)	0.01709 (17)
O1	0.0411 (11)	0.0745 (15)	0.0855 (16)	0.0201 (11)	0.0176 (11)	0.0284 (13)
O2	0.0464 (11)	0.0552 (12)	0.0704 (13)	0.0277 (10)	0.0209 (10)	0.0174 (10)
O3	0.0535 (11)	0.0492 (11)	0.0541 (11)	0.0263 (10)	0.0129 (9)	0.0159 (9)
O4	0.0677 (13)	0.0746 (14)	0.0528 (11)	0.0411 (11)	0.0250 (10)	0.0384 (11)
O5	0.0597 (12)	0.0580 (12)	0.0510 (11)	0.0368 (10)	0.0260 (9)	0.0261 (9)
O6	0.0698 (13)	0.0656 (13)	0.0609 (12)	0.0460 (11)	0.0292 (10)	0.0358 (10)
O7	0.142 (3)	0.114 (3)	0.128 (3)	0.064 (3)	0.058 (2)	0.046 (2)
O1W	0.0866 (18)	0.0680 (17)	0.0727 (16)	0.0291 (15)	0.0095 (15)	0.0053 (14)
N1	0.0402 (12)	0.0448 (12)	0.0470 (12)	0.0196 (10)	0.0124 (10)	0.0178 (10)
N2	0.0416 (12)	0.0447 (12)	0.0466 (12)	0.0214 (10)	0.0145 (10)	0.0229 (10)
N3	0.0407 (13)	0.0551 (15)	0.0554 (14)	0.0178 (11)	0.0092 (11)	0.0235 (12)
N4	0.0418 (11)	0.0421 (11)	0.0465 (12)	0.0237 (10)	0.0160 (10)	0.0231 (10)
N5	0.0397 (11)	0.0404 (11)	0.0451 (12)	0.0202 (9)	0.0126 (9)	0.0210 (10)
N6	0.0615 (15)	0.0576 (15)	0.0560 (14)	0.0335 (13)	0.0234 (12)	0.0355 (12)
N7	0.079 (2)	0.084 (2)	0.085 (2)	0.0233 (18)	0.0087 (18)	0.049 (2)
C1	0.0438 (18)	0.078 (3)	0.087 (3)	0.0036 (18)	−0.0034 (18)	0.030 (2)
C2	0.069 (2)	0.066 (2)	0.0570 (19)	0.0151 (19)	0.0051 (17)	0.0179 (17)
C3	0.0555 (17)	0.0529 (17)	0.0463 (15)	0.0199 (14)	0.0113 (13)	0.0217 (14)
C4	0.0381 (14)	0.0519 (16)	0.0537 (16)	0.0186 (13)	0.0130 (12)	0.0293 (14)
C5	0.0421 (14)	0.0472 (15)	0.0461 (14)	0.0236 (12)	0.0169 (12)	0.0247 (12)
C6	0.0444 (15)	0.0486 (15)	0.0451 (14)	0.0218 (13)	0.0115 (12)	0.0232 (12)
C7	0.0395 (14)	0.0490 (15)	0.0429 (14)	0.0227 (12)	0.0142 (11)	0.0230 (12)
C8	0.0444 (14)	0.0575 (16)	0.0436 (14)	0.0278 (13)	0.0202 (12)	0.0277 (13)
C9	0.0586 (18)	0.0660 (19)	0.0513 (16)	0.0362 (16)	0.0243 (14)	0.0247 (15)
C10	0.078 (2)	0.091 (3)	0.065 (2)	0.057 (2)	0.0374 (18)	0.0368 (19)
C11	0.066 (2)	0.111 (3)	0.074 (2)	0.060 (2)	0.0384 (19)	0.053 (2)
C12	0.0468 (17)	0.091 (2)	0.068 (2)	0.0381 (17)	0.0243 (15)	0.0469 (19)
C13	0.0437 (15)	0.0616 (17)	0.0506 (15)	0.0265 (14)	0.0180 (12)	0.0323 (14)
C14	0.072 (2)	0.089 (2)	0.072 (2)	0.046 (2)	0.0239 (18)	0.057 (2)
C15	0.0578 (18)	0.071 (2)	0.083 (2)	0.0394 (17)	0.0218 (17)	0.0483 (18)
C16	0.0476 (15)	0.0591 (17)	0.0627 (17)	0.0307 (14)	0.0193 (13)	0.0321 (15)
C17	0.0415 (14)	0.0490 (15)	0.0423 (14)	0.0198 (12)	0.0122 (11)	0.0231 (12)
C18	0.0350 (13)	0.0412 (13)	0.0425 (13)	0.0183 (11)	0.0104 (11)	0.0173 (11)
C19	0.0464 (15)	0.0496 (15)	0.0485 (15)	0.0245 (13)	0.0168 (12)	0.0261 (13)
C20	0.0407 (14)	0.0415 (14)	0.0453 (14)	0.0186 (12)	0.0126 (11)	0.0215 (12)
C21	0.0404 (14)	0.0412 (14)	0.0419 (14)	0.0147 (12)	0.0107 (11)	0.0164 (11)
C22	0.0488 (16)	0.0487 (16)	0.0565 (17)	0.0224 (13)	0.0163 (13)	0.0184 (13)
C23	0.0587 (19)	0.0578 (19)	0.0639 (19)	0.0257 (16)	0.0237 (16)	0.0138 (16)
C24	0.063 (2)	0.067 (2)	0.0546 (18)	0.0222 (17)	0.0278 (16)	0.0187 (16)
C25	0.0611 (19)	0.0615 (19)	0.0511 (17)	0.0201 (16)	0.0219 (15)	0.0280 (15)
C26	0.0439 (15)	0.0442 (15)	0.0494 (15)	0.0154 (12)	0.0137 (12)	0.0205 (12)
C27	0.110 (4)	0.114 (4)	0.074 (3)	0.001 (3)	0.023 (3)	0.038 (3)
C28	0.109 (3)	0.104 (3)	0.104 (3)	0.054 (3)	0.036 (3)	0.057 (3)
C29	0.112 (4)	0.115 (4)	0.229 (7)	0.015 (3)	−0.044 (4)	0.113 (5)

Geometric parameters (Å, º) top

Mn1—N2	2.016 (2)	C6—C7	1.470 (4)
Mn1—N5	2.023 (2)	C7—C8	1.437 (3)
Mn1—O5	2.0667 (18)	C8—C9	1.381 (4)
Mn1—O2	2.076 (2)	C8—C13	1.404 (4)
Mn1—O3	2.2676 (19)	C9—C10	1.391 (4)
Mn1—O6	2.2998 (19)	C9—H9	0.93
O1—C1	1.364 (4)	C10—C11	1.381 (5)
O1—C4	1.367 (3)	C10—H10	0.93
O2—C5	1.261 (3)	C11—C12	1.385 (5)
O3—C6	1.243 (3)	C11—H11	0.93
O4—C14	1.359 (4)	C12—C13	1.371 (4)
O4—C17	1.372 (3)	C12—H12	0.93
O5—C18	1.255 (3)	C14—C15	1.336 (5)
O6—C19	1.249 (3)	C14—H14	0.93
O7—C27	1.231 (7)	C15—C16	1.413 (4)
O1W—H1W1	0.86 (1)	C15—H15	0.93
O1W—H1W2	0.86 (1)	C16—C17	1.350 (4)
N1—N2	1.341 (3)	C16—H16	0.93
N1—C5	1.353 (3)	C17—C18	1.446 (3)
N2—C7	1.301 (3)	C19—C20	1.466 (4)
N3—C6	1.346 (3)	C20—C21	1.443 (4)
N3—C13	1.411 (4)	C21—C22	1.379 (4)
N3—H3	0.86 (1)	C21—C26	1.407 (4)
N4—N5	1.343 (3)	C22—C23	1.385 (4)
N4—C18	1.361 (3)	C22—H22	0.93
N5—C20	1.301 (3)	C23—C24	1.391 (5)
N6—C19	1.348 (3)	C23—H23	0.93
N6—C26	1.415 (4)	C24—C25	1.383 (4)
N6—H6	0.87 (1)	C24—H24	0.93
N7—C27	1.330 (7)	C25—C26	1.369 (4)
N7—C28	1.419 (5)	C25—H25	0.93
N7—C29	1.438 (5)	C27—H27	0.93
C1—C2	1.325 (5)	C28—H28A	0.96
C1—H1	0.93	C28—H28B	0.96
C2—C3	1.408 (4)	C28—H28C	0.96
C2—H2	0.93	C29—H29A	0.96
C3—C4	1.342 (4)	C29—H29B	0.96
C3—H3A	0.93	C29—H29C	0.96
C4—C5	1.448 (4)

N2—Mn1—N5	171.59 (8)	C11—C10—C9	120.4 (3)
N2—Mn1—O5	111.99 (8)	C11—C10—H10	119.8
N5—Mn1—O5	75.50 (7)	C9—C10—H10	119.8
N2—Mn1—O2	75.65 (8)	C10—C11—C12	122.4 (3)
N5—Mn1—O2	100.19 (8)	C10—C11—H11	118.8
O5—Mn1—O2	96.41 (8)	C12—C11—H11	118.8
N2—Mn1—O3	78.39 (8)	C13—C12—C11	116.9 (3)
N5—Mn1—O3	105.49 (8)	C13—C12—H12	121.6
O5—Mn1—O3	93.69 (7)	C11—C12—H12	121.6
O2—Mn1—O3	154.03 (7)	C12—C13—C8	121.7 (3)
N2—Mn1—O6	95.06 (8)	C12—C13—N3	128.3 (3)
N5—Mn1—O6	77.73 (7)	C8—C13—N3	110.0 (2)
O5—Mn1—O6	152.77 (7)	C15—C14—O4	111.3 (3)
O2—Mn1—O6	93.09 (8)	C15—C14—H14	124.3
O3—Mn1—O6	88.68 (7)	O4—C14—H14	124.3
C1—O1—C4	104.9 (3)	C14—C15—C16	106.3 (3)
C5—O2—Mn1	110.94 (16)	C14—C15—H15	126.9
C6—O3—Mn1	105.12 (16)	C16—C15—H15	126.9
C14—O4—C17	105.7 (2)	C17—C16—C15	106.8 (3)
C18—O5—Mn1	111.41 (15)	C17—C16—H16	126.6
C19—O6—Mn1	105.01 (15)	C15—C16—H16	126.6
H1W1—O1W—H1W2	103 (4)	C16—C17—O4	109.9 (2)
N2—N1—C5	107.4 (2)	C16—C17—C18	132.7 (2)
C7—N2—N1	122.6 (2)	O4—C17—C18	117.3 (2)
C7—N2—Mn1	117.46 (18)	O5—C18—N4	125.9 (2)
N1—N2—Mn1	119.86 (16)	O5—C18—C17	120.5 (2)
C6—N3—C13	110.2 (2)	N4—C18—C17	113.6 (2)
C6—N3—H3	124 (2)	O6—C19—N6	127.8 (2)
C13—N3—H3	125 (2)	O6—C19—C20	125.0 (2)
N5—N4—C18	107.04 (19)	N6—C19—C20	107.2 (2)
C20—N5—N4	122.4 (2)	N5—C20—C21	138.0 (2)
C20—N5—Mn1	117.93 (17)	N5—C20—C19	114.3 (2)
N4—N5—Mn1	119.52 (15)	C21—C20—C19	107.7 (2)
C19—N6—C26	110.0 (2)	C22—C21—C26	120.3 (2)
C19—N6—H6	122 (2)	C22—C21—C20	134.3 (2)
C26—N6—H6	128 (2)	C26—C21—C20	105.4 (2)
C27—N7—C28	118.5 (4)	C21—C22—C23	118.1 (3)
C27—N7—C29	121.1 (5)	C21—C22—H22	121.0
C28—N7—C29	120.5 (5)	C23—C22—H22	121.0
C2—C1—O1	111.8 (3)	C22—C23—C24	120.9 (3)
C2—C1—H1	124.1	C22—C23—H23	119.6
O1—C1—H1	124.1	C24—C23—H23	119.6
C1—C2—C3	106.0 (3)	C25—C24—C23	121.5 (3)
C1—C2—H2	127.0	C25—C24—H24	119.2
C3—C2—H2	127.0	C23—C24—H24	119.2
C4—C3—C2	106.9 (3)	C26—C25—C24	117.4 (3)
C4—C3—H3A	126.5	C26—C25—H25	121.3
C2—C3—H3A	126.5	C24—C25—H25	121.3
C3—C4—O1	110.3 (2)	C25—C26—C21	121.9 (3)
C3—C4—C5	133.2 (3)	C25—C26—N6	128.5 (3)
O1—C4—C5	116.5 (2)	C21—C26—N6	109.6 (2)
O2—C5—N1	126.0 (2)	O7—C27—N7	123.8 (5)
O2—C5—C4	120.4 (2)	O7—C27—H27	118.1
N1—C5—C4	113.6 (2)	N7—C27—H27	118.1
O3—C6—N3	128.2 (3)	N7—C28—H28A	109.5
O3—C6—C7	125.2 (2)	N7—C28—H28B	109.5
N3—C6—C7	106.6 (2)	H28A—C28—H28B	109.5
N2—C7—C8	138.1 (3)	N7—C28—H28C	109.5
N2—C7—C6	113.7 (2)	H28A—C28—H28C	109.5
C8—C7—C6	108.2 (2)	H28B—C28—H28C	109.5
C9—C8—C13	120.6 (3)	N7—C29—H29A	109.5
C9—C8—C7	134.3 (3)	N7—C29—H29B	109.5
C13—C8—C7	105.0 (2)	H29A—C29—H29B	109.5
C8—C9—C10	117.8 (3)	N7—C29—H29C	109.5
C8—C9—H9	121.1	H29A—C29—H29C	109.5
C10—C9—H9	121.1	H29B—C29—H29C	109.5

N2—Mn1—O2—C5	2.65 (17)	O3—C6—C7—C8	179.1 (2)
N5—Mn1—O2—C5	175.17 (17)	N3—C6—C7—C8	0.2 (3)
O5—Mn1—O2—C5	−108.46 (18)	N2—C7—C8—C9	0.4 (5)
O3—Mn1—O2—C5	3.8 (3)	C6—C7—C8—C9	−178.8 (3)
O6—Mn1—O2—C5	97.10 (18)	N2—C7—C8—C13	179.3 (3)
N2—Mn1—O3—C6	3.01 (16)	C6—C7—C8—C13	0.0 (3)
N5—Mn1—O3—C6	−169.32 (16)	C13—C8—C9—C10	−0.5 (4)
O5—Mn1—O3—C6	114.71 (16)	C7—C8—C9—C10	178.2 (3)
O2—Mn1—O3—C6	1.9 (3)	C8—C9—C10—C11	1.2 (5)
O6—Mn1—O3—C6	−92.44 (17)	C9—C10—C11—C12	−1.2 (5)
N2—Mn1—O5—C18	−169.67 (16)	C10—C11—C12—C13	0.4 (5)
N5—Mn1—O5—C18	6.30 (17)	C11—C12—C13—C8	0.2 (4)
O2—Mn1—O5—C18	−92.60 (17)	C11—C12—C13—N3	−178.6 (3)
O3—Mn1—O5—C18	111.36 (17)	C9—C8—C13—C12	−0.2 (4)
O6—Mn1—O5—C18	17.1 (3)	C7—C8—C13—C12	−179.2 (2)
N2—Mn1—O6—C19	172.82 (18)	C9—C8—C13—N3	178.8 (2)
N5—Mn1—O6—C19	−2.79 (17)	C7—C8—C13—N3	−0.2 (3)
O5—Mn1—O6—C19	−13.5 (3)	C6—N3—C13—C12	179.3 (3)
O2—Mn1—O6—C19	96.97 (18)	C6—N3—C13—C8	0.3 (3)
O3—Mn1—O6—C19	−108.96 (18)	C17—O4—C14—C15	0.3 (4)
C5—N1—N2—C7	−177.6 (2)	O4—C14—C15—C16	−0.3 (4)
C5—N1—N2—Mn1	−0.9 (3)	C14—C15—C16—C17	0.2 (4)
O5—Mn1—N2—C7	−92.86 (19)	C15—C16—C17—O4	0.0 (3)
O2—Mn1—N2—C7	175.9 (2)	C15—C16—C17—C18	−177.2 (3)
O3—Mn1—N2—C7	−3.56 (18)	C14—O4—C17—C16	−0.1 (3)
O6—Mn1—N2—C7	84.04 (19)	C14—O4—C17—C18	177.5 (2)
O5—Mn1—N2—N1	90.30 (18)	Mn1—O5—C18—N4	−5.7 (3)
O2—Mn1—N2—N1	−0.89 (17)	Mn1—O5—C18—C17	174.99 (18)
O3—Mn1—N2—N1	179.61 (18)	N5—N4—C18—O5	0.0 (3)
O6—Mn1—N2—N1	−92.79 (18)	N5—N4—C18—C17	179.4 (2)
C18—N4—N5—C20	−179.0 (2)	C16—C17—C18—O5	177.8 (3)
C18—N4—N5—Mn1	6.2 (2)	O4—C17—C18—O5	0.9 (4)
O5—Mn1—N5—C20	177.8 (2)	C16—C17—C18—N4	−1.6 (4)
O2—Mn1—N5—C20	−88.14 (19)	O4—C17—C18—N4	−178.5 (2)
O3—Mn1—N5—C20	87.97 (19)	Mn1—O6—C19—N6	−175.7 (2)
O6—Mn1—N5—C20	2.83 (18)	Mn1—O6—C19—C20	2.7 (3)
O5—Mn1—N5—N4	−7.14 (16)	C26—N6—C19—O6	178.8 (3)
O2—Mn1—N5—N4	86.91 (18)	C26—N6—C19—C20	0.2 (3)
O3—Mn1—N5—N4	−96.98 (17)	N4—N5—C20—C21	0.2 (5)
O6—Mn1—N5—N4	177.88 (18)	Mn1—N5—C20—C21	175.1 (3)
C4—O1—C1—C2	−0.1 (4)	N4—N5—C20—C19	−177.3 (2)
O1—C1—C2—C3	0.0 (4)	Mn1—N5—C20—C19	−2.4 (3)
C1—C2—C3—C4	0.0 (4)	O6—C19—C20—N5	−0.6 (4)
C2—C3—C4—O1	−0.1 (3)	N6—C19—C20—N5	178.1 (2)
C2—C3—C4—C5	179.2 (3)	O6—C19—C20—C21	−178.9 (3)
C1—O1—C4—C3	0.1 (3)	N6—C19—C20—C21	−0.2 (3)
C1—O1—C4—C5	−179.3 (3)	N5—C20—C21—C22	2.7 (6)
Mn1—O2—C5—N1	−4.7 (3)	C19—C20—C21—C22	−179.7 (3)
Mn1—O2—C5—C4	176.15 (18)	N5—C20—C21—C26	−177.5 (3)
N2—N1—C5—O2	3.9 (3)	C19—C20—C21—C26	0.1 (3)
N2—N1—C5—C4	−176.9 (2)	C26—C21—C22—C23	−0.5 (4)
C3—C4—C5—O2	−172.0 (3)	C20—C21—C22—C23	179.3 (3)
O1—C4—C5—O2	7.2 (4)	C21—C22—C23—C24	0.9 (4)
C3—C4—C5—N1	8.7 (4)	C22—C23—C24—C25	−0.6 (5)
O1—C4—C5—N1	−172.1 (2)	C23—C24—C25—C26	−0.1 (5)
Mn1—O3—C6—N3	176.3 (2)	C24—C25—C26—C21	0.5 (4)
Mn1—O3—C6—C7	−2.4 (3)	C24—C25—C26—N6	−179.5 (3)
C13—N3—C6—O3	−179.2 (3)	C22—C21—C26—C25	−0.2 (4)
C13—N3—C6—C7	−0.3 (3)	C20—C21—C26—C25	180.0 (2)
N1—N2—C7—C8	1.0 (5)	C22—C21—C26—N6	179.8 (2)
Mn1—N2—C7—C8	−175.8 (3)	C20—C21—C26—N6	0.0 (3)
N1—N2—C7—C6	−179.9 (2)	C19—N6—C26—C25	179.9 (3)
Mn1—N2—C7—C6	3.4 (3)	C19—N6—C26—C21	−0.1 (3)
O3—C6—C7—N2	−0.3 (4)	C28—N7—C27—O7	2.2 (7)
N3—C6—C7—N2	−179.3 (2)	C29—N7—C27—O7	−178.0 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O3	0.86 (1)	2.06 (2)	2.896 (3)	165 (4)
O1W—H1W2···O7	0.86 (1)	1.93 (2)	2.762 (5)	161 (4)
N3—H3···O1Wⁱ	0.86 (1)	1.96 (1)	2.811 (4)	176 (3)
N6—H6···O6ⁱⁱ	0.87 (1)	2.05 (1)	2.899 (3)	167 (3)

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

Experimental details

Crystal data
Chemical formula	[Mn(C₁₃H₈N₃O₃)₂]·C₃H₇NO·H₂O
M_r	654.50
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	11.4833 (7), 11.5599 (7), 13.1619 (8)
α, β, γ (°)	107.580 (1), 97.800 (1), 115.159 (1)
V (Å³)	1435.21 (15)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.53
Crystal size (mm)	0.45 × 0.32 × 0.20

Data collection
Diffractometer	Bruker SMART area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.798, 0.902
No. of measured, independent and observed [I > 2˘I)] reflections	12170, 6180, 4297
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.641

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.126, 0.95
No. of reflections	6180
No. of parameters	420
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.61, −0.26

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Mn1—N2	2.016 (2)	Mn1—O2	2.076 (2)
Mn1—N5	2.023 (2)	Mn1—O3	2.2676 (19)
Mn1—O5	2.0667 (18)	Mn1—O6	2.2998 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O3	0.86 (1)	2.06 (2)	2.896 (3)	165 (4)
O1W—H1W2···O7	0.86 (1)	1.93 (2)	2.762 (5)	161 (4)
N3—H3···O1Wⁱ	0.86 (1)	1.96 (1)	2.811 (4)	176 (3)
N6—H6···O6ⁱⁱ	0.87 (1)	2.05 (1)	2.899 (3)	167 (3)

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

Acknowledgements

The authors thank the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
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Rodríguez-Argüelles, M. C., Cao, R., García-Deibe, A. M., Pelizzi, C., Sanmartín-Matalobos, J. & Zani, F. (2009). Polyhedron, 28, 2187–2195. Google Scholar
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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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