(Benzoato-κ2O,O′)(quinoline-2-carboxyl­ato-κ2N,O)(quinoline-2-carboxylic acid-κ2N,O)manganese(II)

Martins, N.D.; Silva, J.A.; Ramos Silva, M.; Matos Beja, A.; Sobral, A.J.F.N.

doi:10.1107/S1600536807066809

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page m258

https://doi.org/10.1107/S1600536807066809

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(Benzoato-κ²O,O′)(quinoline-2-carboxylato-κ²N,O)(quinoline-2-carboxylic acid-κ²N,O)manganese(II)

Nuno D. Martins,^a Joana A. Silva,^b Manuela Ramos Silva,^a ^* Ana Matos Beja ^a and Abilio J. F.N. Sobral ^b

^aCEMDRX, Physics Department, University of Coimbra, P-3004-516 Coimbra, Portugal, and ^bChemistry Department, University of Coimbra, P-3004-516 Coimbra, Portugal
^*Correspondence e-mail: manuela@pollux.fis.uc.pt

(Received 29 November 2007; accepted 13 December 2007; online 21 December 2007)

The crystal structure of the title compound, [Mn(C₇H₅O₂)(C₁₀H₆NO₂)(C₁₀H₇NO₂)], contains manganese(II) ions six-coordinated in a distorted octahedral environment. The equatorial plane is occupied by four O atoms, two from the carboxylate group of the benzoate ion, the other two from carboxylate/carboxyl groups of the quinaldate/quinaldic acid molecules. The axial positions are occupied by the N atoms of the quinoline ring systems. The metal ion lies on a twofold rotation axis that bisects the benzoate ligand; the quinaldate and quinaldic acid ligands are therefore equivalent by symmetry, and the carboxylate/carboxyl groups are disordered. The complexes are joined together by hydrogen bonds between the carboxylate/carboxyl groups of adjacent quinaldate/quinaldic acid molecules, forming zigzag chains that run along the c axis.

Related literature

For related literature, see Zurowska et al. (2007 ); Dobrzynska et al. (2005 ); Kumar & Gandotra (1980 ); Catterick et al. (1974 ).

Experimental

Crystal data

[Mn(C₇H₅O₂)(C₁₀H₆NO₂)(C₁₀H₇NO₂)]
M_r = 521.37
Monoclinic, C 2/c
a = 19.3839 (4) Å
b = 11.6775 (2) Å
c = 11.6306 (2) Å
β = 117.288 (1)°
V = 2339.67 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.61 mm⁻¹
T = 293 (2) K
0.24 × 0.22 × 0.15 mm

Data collection

Bruker APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ) T_min = 0.883, T_max = 0.908
25798 measured reflections
2917 independent reflections
2413 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.149
S = 1.08
2917 reflections
169 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.68 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3ⁱ	0.96 (7)	1.70 (7)	2.621 (4)	160 (6)
Symmetry code: (i) -x+1, -y, -z.

Data collection: SMART (Bruker, 2003 ); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807066809/bt2660sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807066809/bt2660Isup2.hkl

checkCIF report

Comment top

Some compounds with quinoline derivatives, transition metal ions and halide ions exhibit interesting magnetic properties related with the formation of low dimensional elements (Zurowska et al., 2007; Dobrzynska et al., 2005; Kumar & Gandotra, 1980; Catterick et al., 1974). The crystal structure of the title compound, Mn(C₇H₅O₂) (C₁₀H₇NO₂)(C₁₀H₆NO₂), consists of manganese(II) ions six-coordinated in a distorted octahedral environment (Fig. 1). The basal plane is occupied by four oxygen atoms with Mn—O distances ranging from 2.1293 (18) to 2.2858 (19) Å. Two basal oxygen atoms belong to the carboxylate group of the benzoate ion, that chelates the metal ion in the usual bidentate mode. Each of the two quinoline molecules supply another O atom to the Mn coordination environment. The apical positions are occupied by the nitrogen atoms of the quinoline ring system, with a distance of 2.2858 (19) Å. Both the benzoic acid and quinoline-2-carboxylic acid molecules are planar. The maximum deviation from the quinolinic plane is 0.1040 (9)Å for O2. The maximum deviation from the benzoic plane is 0.013 (2)Å for O1. The two planes make an angle of 82.98 (9)°. The complexes are joined together by hydrogen bonds, between the carboxylate/carboxylic groups of the quinaldic acid molecules (Fig. 2). The shared hydrogen atom is disordered and the quinoline molecules are statistically neutral or negatively charged. Such H-bonds delineate zigzag chains that run along the c axis (Fig. 3).

Related literature top

For related literature, see Zurowska et al. (2007); Dobrzynska et al. (2005); Kumar & Gandotra (1980); Catterick et al. (1974).

Experimental top

Approximately 0.13 mmol of 2-quinolinecarboxaldehyde (Sigma, 97%) were dissolved in 2 ml of dimethylformamide and then 0.14 mmol of benzoic acid were added to the solution. 0.12 mmol of manganese chloride tetrahydrated dissolved in 1 ml of water were also added to the former solution. After one month, single crystals of suitable quality were grown from the solution. The refined structure shows that the crystals incorporated a different quinoline derivative than that expected showing that the material purchased from Sigma was contaminated.

Structure description top

For related literature, see Zurowska et al. (2007); Dobrzynska et al. (2005); Kumar & Gandotra (1980); Catterick et al. (1974).

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

	Fig. 1. ORTEPII (Johnson, 1976) plot of the title compound. Displacement ellipsoids are drawn at the 50% level.
	Fig. 2. Two of the complexes joined by a hydrogen bond (depicted as a dashed line) between the carboxylic/carboxylate groups of the quinoline molecule.

(Benzoato-κ²O,O')(quinoline-2-carboxylato-κ²N,O)(quinoline-2-carboxylic acid-κ²N,O)manganese(II) top

Crystal data top

[Mn(C₇H₅O₂)(C₁₀H₆NO₂)(C₁₀H₇NO₂)]	F(000) = 1068
M_r = 521.37	D_x = 1.480 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 19.3839 (4) Å	Cell parameters from 8901 reflections
b = 11.6775 (2) Å	θ = 2.4–27.5°
c = 11.6306 (2) Å	µ = 0.61 mm⁻¹
β = 117.288 (1)°	T = 293 K
V = 2339.67 (8) Å³	Prism, pink
Z = 4	0.24 × 0.22 × 0.15 mm

Data collection top

Bruker APEX CCD area-detector diffractometer	2917 independent reflections
Radiation source: fine-focus sealed tube	2413 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
φ and ω scans	θ_max = 28.4°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −25→25
T_min = 0.883, T_max = 0.908	k = −15→15
25798 measured reflections	l = −15→15

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.149	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.0806P)² + 2.8119P] where P = (F_o² + 2F_c²)/3
2917 reflections	(Δ/σ)_max < 0.001
169 parameters	Δρ_max = 0.68 e Å⁻³
1 restraint	Δρ_min = −0.50 e Å⁻³

Crystal data top

[Mn(C₇H₅O₂)(C₁₀H₆NO₂)(C₁₀H₇NO₂)]	V = 2339.67 (8) Å³
M_r = 521.37	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 19.3839 (4) Å	µ = 0.61 mm⁻¹
b = 11.6775 (2) Å	T = 293 K
c = 11.6306 (2) Å	0.24 × 0.22 × 0.15 mm
β = 117.288 (1)°

Data collection top

Bruker APEX CCD area-detector diffractometer	2917 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	2413 reflections with I > 2σ(I)
T_min = 0.883, T_max = 0.908	R_int = 0.027
25798 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	1 restraint
wR(F²) = 0.149	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.68 e Å⁻³
2917 reflections	Δρ_min = −0.50 e Å⁻³
169 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Mn1	0.5000	0.20556 (4)	0.2500	0.03799 (18)
O1	0.48852 (12)	0.37094 (15)	0.14858 (17)	0.0505 (4)
O2	0.48495 (10)	0.09330 (17)	0.09597 (18)	0.0508 (5)
H2	0.525 (3)	0.041 (5)	0.103 (7)	0.07 (2)*	0.50
N1	0.37188 (11)	0.15467 (17)	0.15100 (18)	0.0378 (4)
C1	0.5000	0.4239 (3)	0.2500	0.0395 (7)
C2	0.5000	0.5526 (3)	0.2500	0.0359 (6)
C3	0.48852 (16)	0.6123 (2)	0.1396 (2)	0.0457 (6)
H3	0.4807	0.5728	0.0652	0.055*
C4	0.4888 (2)	0.7302 (3)	0.1403 (3)	0.0569 (7)
H4	0.4813	0.7702	0.0664	0.068*
C5	0.5000	0.7889 (3)	0.2500	0.0582 (10)
H5	0.5000	0.8685	0.2500	0.070*
C6	0.41618 (15)	0.0511 (3)	0.0173 (3)	0.0521 (6)
O3	0.39792 (16)	0.0125 (4)	−0.0885 (3)	0.1252 (15)
C7	0.35213 (13)	0.0869 (2)	0.0500 (2)	0.0402 (5)
C15	0.31580 (14)	0.1843 (2)	0.1866 (2)	0.0418 (5)
C10	0.23875 (14)	0.1435 (2)	0.1169 (3)	0.0487 (6)
C9	0.22055 (15)	0.0739 (3)	0.0085 (3)	0.0553 (7)
H9	0.1701	0.0476	−0.0404	0.066*
C8	0.27651 (15)	0.0452 (2)	−0.0249 (3)	0.0501 (6)
H8	0.2652	−0.0014	−0.0963	0.060*
C11	0.18377 (18)	0.1752 (3)	0.1597 (4)	0.0668 (9)
H11	0.1327	0.1500	0.1148	0.080*
C12	0.2053 (2)	0.2419 (4)	0.2655 (4)	0.0790 (11)
H12	0.1690	0.2608	0.2938	0.095*
C13	0.2808 (2)	0.2828 (3)	0.3327 (3)	0.0710 (9)
H13	0.2942	0.3292	0.4049	0.085*
C14	0.33583 (17)	0.2557 (3)	0.2942 (3)	0.0551 (7)
H14	0.3860	0.2844	0.3389	0.066*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0367 (3)	0.0369 (3)	0.0406 (3)	0.000	0.0179 (2)	0.000
O1	0.0663 (12)	0.0394 (9)	0.0450 (9)	−0.0012 (8)	0.0248 (9)	−0.0037 (7)
O2	0.0375 (9)	0.0580 (11)	0.0577 (10)	−0.0023 (8)	0.0226 (8)	−0.0194 (9)
N1	0.0344 (9)	0.0405 (10)	0.0380 (9)	0.0031 (8)	0.0162 (8)	0.0023 (8)
C1	0.0338 (15)	0.0405 (16)	0.0427 (16)	0.000	0.0161 (13)	0.000
C2	0.0321 (14)	0.0367 (16)	0.0402 (15)	0.000	0.0178 (12)	0.000
C3	0.0552 (14)	0.0469 (13)	0.0379 (11)	−0.0038 (11)	0.0238 (11)	−0.0019 (10)
C4	0.076 (2)	0.0496 (15)	0.0481 (14)	−0.0032 (14)	0.0305 (14)	0.0087 (12)
C5	0.075 (3)	0.0352 (18)	0.065 (2)	0.000	0.033 (2)	0.000
C6	0.0408 (13)	0.0669 (17)	0.0482 (13)	0.0026 (12)	0.0201 (11)	−0.0100 (13)
O3	0.0565 (15)	0.199 (4)	0.117 (2)	−0.0191 (18)	0.0365 (15)	−0.111 (3)
C7	0.0346 (11)	0.0402 (12)	0.0432 (12)	0.0024 (9)	0.0157 (9)	0.0034 (10)
C15	0.0360 (11)	0.0464 (13)	0.0440 (12)	0.0093 (9)	0.0193 (10)	0.0103 (10)
C10	0.0340 (12)	0.0548 (15)	0.0575 (15)	0.0096 (11)	0.0211 (11)	0.0161 (12)
C9	0.0345 (12)	0.0608 (16)	0.0625 (16)	−0.0049 (11)	0.0152 (11)	0.0050 (14)
C8	0.0415 (13)	0.0508 (14)	0.0497 (14)	−0.0044 (11)	0.0137 (11)	−0.0047 (12)
C11	0.0428 (15)	0.088 (2)	0.078 (2)	0.0158 (15)	0.0348 (15)	0.0171 (18)
C12	0.064 (2)	0.105 (3)	0.088 (2)	0.033 (2)	0.0518 (19)	0.018 (2)
C13	0.069 (2)	0.089 (3)	0.0659 (19)	0.0200 (18)	0.0405 (17)	−0.0030 (17)
C14	0.0501 (15)	0.0647 (17)	0.0522 (15)	0.0115 (13)	0.0249 (13)	−0.0014 (13)

Geometric parameters (Å, º) top

Mn1—O2ⁱ	2.1293 (18)	C5—C4ⁱ	1.375 (3)
Mn1—O2	2.1293 (18)	C5—H5	0.9300
Mn1—O1ⁱ	2.2203 (19)	C6—O3	1.200 (4)
Mn1—O1	2.2203 (19)	C6—C7	1.515 (3)
Mn1—N1	2.2858 (19)	C7—C8	1.405 (3)
Mn1—N1ⁱ	2.2858 (19)	C15—C14	1.401 (4)
Mn1—C1	2.550 (3)	C15—C10	1.416 (4)
O1—C1	1.258 (2)	C10—C9	1.403 (4)
O2—C6	1.319 (3)	C10—C11	1.416 (4)
O2—H2	0.959 (10)	C9—C8	1.352 (4)
N1—C7	1.319 (3)	C9—H9	0.9300
N1—C15	1.373 (3)	C8—H8	0.9300
C1—O1ⁱ	1.258 (2)	C11—C12	1.350 (6)
C1—C2	1.503 (5)	C11—H11	0.9300
C2—C3	1.386 (3)	C12—C13	1.390 (6)
C2—C3ⁱ	1.386 (3)	C12—H12	0.9300
C3—C4	1.377 (4)	C13—C14	1.370 (4)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.375 (3)	C14—H14	0.9300
C4—H4	0.9300

O2ⁱ—Mn1—O2	104.00 (12)	C4—C3—H3	120.0
O2ⁱ—Mn1—O1ⁱ	98.44 (7)	C2—C3—H3	120.0
O2—Mn1—O1ⁱ	157.55 (8)	C5—C4—C3	120.2 (3)
O2ⁱ—Mn1—O1	157.55 (8)	C5—C4—H4	119.9
O2—Mn1—O1	98.44 (7)	C3—C4—H4	119.9
O1ⁱ—Mn1—O1	59.13 (9)	C4—C5—C4ⁱ	120.2 (4)
O2ⁱ—Mn1—N1	87.81 (7)	C4—C5—H5	119.9
O2—Mn1—N1	73.62 (7)	C4ⁱ—C5—H5	119.9
O1ⁱ—Mn1—N1	108.35 (7)	O3—C6—O2	125.5 (3)
O1—Mn1—N1	97.90 (7)	O3—C6—C7	118.1 (2)
O2ⁱ—Mn1—N1ⁱ	73.62 (7)	O2—C6—C7	114.0 (2)
O2—Mn1—N1ⁱ	87.81 (7)	N1—C7—C8	123.7 (2)
O1ⁱ—Mn1—N1ⁱ	97.90 (7)	N1—C7—C6	116.9 (2)
O1—Mn1—N1ⁱ	108.35 (7)	C8—C7—C6	119.3 (2)
N1—Mn1—N1ⁱ	149.86 (10)	N1—C15—C14	119.0 (2)
O2ⁱ—Mn1—C1	128.00 (6)	N1—C15—C10	121.0 (2)
O2—Mn1—C1	128.00 (6)	C14—C15—C10	119.9 (2)
O1ⁱ—Mn1—C1	29.57 (4)	C9—C10—C15	118.3 (2)
O1—Mn1—C1	29.57 (5)	C9—C10—C11	123.2 (3)
N1—Mn1—C1	105.07 (5)	C15—C10—C11	118.5 (3)
N1ⁱ—Mn1—C1	105.07 (5)	C8—C9—C10	119.9 (2)
C1—O1—Mn1	89.89 (16)	C8—C9—H9	120.1
C6—O2—Mn1	121.28 (15)	C10—C9—H9	120.1
C6—O2—H2	110 (4)	C9—C8—C7	118.8 (3)
Mn1—O2—H2	122 (4)	C9—C8—H8	120.6
C7—N1—C15	118.2 (2)	C7—C8—H8	120.6
C7—N1—Mn1	114.17 (15)	C12—C11—C10	120.1 (3)
C15—N1—Mn1	127.58 (16)	C12—C11—H11	119.9
O1—C1—O1ⁱ	121.1 (3)	C10—C11—H11	119.9
O1—C1—C2	119.46 (16)	C11—C12—C13	121.2 (3)
O1ⁱ—C1—C2	119.46 (16)	C11—C12—H12	119.4
O1—C1—Mn1	60.54 (16)	C13—C12—H12	119.4
O1ⁱ—C1—Mn1	60.54 (16)	C14—C13—C12	120.8 (3)
C2—C1—Mn1	180.0	C14—C13—H13	119.6
C3—C2—C3ⁱ	119.6 (3)	C12—C13—H13	119.6
C3—C2—C1	120.20 (16)	C13—C14—C15	119.4 (3)
C3ⁱ—C2—C1	120.20 (16)	C13—C14—H14	120.3
C4—C3—C2	119.9 (2)	C15—C14—H14	120.3

O2ⁱ—Mn1—O1—C1	3.1 (2)	O1—C1—C2—C3	−0.90 (17)
O2—Mn1—O1—C1	−178.80 (10)	O1ⁱ—C1—C2—C3	179.10 (17)
O1ⁱ—Mn1—O1—C1	0.0	Mn1—C1—C2—C3	−108 (100)
N1—Mn1—O1—C1	106.70 (10)	O1—C1—C2—C3ⁱ	179.10 (17)
N1ⁱ—Mn1—O1—C1	−88.30 (11)	O1ⁱ—C1—C2—C3ⁱ	−0.90 (17)
O2ⁱ—Mn1—O2—C6	85.4 (2)	Mn1—C1—C2—C3ⁱ	72 (100)
O1ⁱ—Mn1—O2—C6	−96.5 (3)	C3ⁱ—C2—C3—C4	0.2 (2)
O1—Mn1—O2—C6	−93.8 (2)	C1—C2—C3—C4	−179.8 (2)
N1—Mn1—O2—C6	2.0 (2)	C2—C3—C4—C5	−0.3 (4)
N1ⁱ—Mn1—O2—C6	157.9 (2)	C3—C4—C5—C4ⁱ	0.2 (2)
C1—Mn1—O2—C6	−94.6 (2)	Mn1—O2—C6—O3	160.0 (3)
O2ⁱ—Mn1—N1—C7	−107.04 (17)	Mn1—O2—C6—C7	−1.8 (3)
O2—Mn1—N1—C7	−1.76 (16)	C15—N1—C7—C8	1.4 (4)
O1ⁱ—Mn1—N1—C7	154.79 (16)	Mn1—N1—C7—C8	179.9 (2)
O1—Mn1—N1—C7	94.77 (17)	C15—N1—C7—C6	−177.1 (2)
N1ⁱ—Mn1—N1—C7	−55.92 (15)	Mn1—N1—C7—C6	1.5 (3)
C1—Mn1—N1—C7	124.07 (15)	O3—C6—C7—N1	−163.2 (3)
O2ⁱ—Mn1—N1—C15	71.34 (19)	O2—C6—C7—N1	0.1 (4)
O2—Mn1—N1—C15	176.6 (2)	O3—C6—C7—C8	18.3 (5)
O1ⁱ—Mn1—N1—C15	−26.8 (2)	O2—C6—C7—C8	−178.5 (2)
O1—Mn1—N1—C15	−86.85 (19)	C7—N1—C15—C14	179.6 (2)
N1ⁱ—Mn1—N1—C15	122.46 (19)	Mn1—N1—C15—C14	1.3 (3)
C1—Mn1—N1—C15	−57.55 (19)	C7—N1—C15—C10	−0.1 (3)
Mn1—O1—C1—O1ⁱ	0.000 (1)	Mn1—N1—C15—C10	−178.43 (17)
Mn1—O1—C1—C2	180.0	N1—C15—C10—C9	−1.4 (4)
O2ⁱ—Mn1—C1—O1	−178.49 (12)	C14—C15—C10—C9	178.9 (3)
O2—Mn1—C1—O1	1.51 (12)	N1—C15—C10—C11	178.8 (2)
O1ⁱ—Mn1—C1—O1	180.0	C14—C15—C10—C11	−0.9 (4)
N1—Mn1—C1—O1	−79.27 (12)	C15—C10—C9—C8	1.7 (4)
N1ⁱ—Mn1—C1—O1	100.73 (12)	C11—C10—C9—C8	−178.6 (3)
O2ⁱ—Mn1—C1—O1ⁱ	1.51 (12)	C10—C9—C8—C7	−0.5 (4)
O2—Mn1—C1—O1ⁱ	−178.49 (12)	N1—C7—C8—C9	−1.1 (4)
O1—Mn1—C1—O1ⁱ	180.000 (1)	C6—C7—C8—C9	177.3 (3)
N1—Mn1—C1—O1ⁱ	100.73 (12)	C9—C10—C11—C12	179.6 (3)
N1ⁱ—Mn1—C1—O1ⁱ	−79.27 (12)	C15—C10—C11—C12	−0.7 (5)
O2ⁱ—Mn1—C1—C2	−72 (100)	C10—C11—C12—C13	1.4 (6)
O2—Mn1—C1—C2	108 (100)	C11—C12—C13—C14	−0.6 (6)
O1ⁱ—Mn1—C1—C2	−73 (100)	C12—C13—C14—C15	−1.0 (5)
O1—Mn1—C1—C2	107 (100)	N1—C15—C14—C13	−178.0 (3)
N1—Mn1—C1—C2	28 (100)	C10—C15—C14—C13	1.7 (4)
N1ⁱ—Mn1—C1—C2	−152 (100)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3ⁱⁱ	0.96 (7)	1.70 (7)	2.621 (4)	160 (6)

Symmetry code: (ii) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formula	[Mn(C₇H₅O₂)(C₁₀H₆NO₂)(C₁₀H₇NO₂)]
M_r	521.37
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	19.3839 (4), 11.6775 (2), 11.6306 (2)
β (°)	117.288 (1)
V (Å³)	2339.67 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.61
Crystal size (mm)	0.24 × 0.22 × 0.15

Data collection
Diffractometer	Bruker APEX CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2000)
T_min, T_max	0.883, 0.908
No. of measured, independent and observed [I > 2σ(I)] reflections	25798, 2917, 2413
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.149, 1.08
No. of reflections	2917
No. of parameters	169
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.68, −0.50

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3ⁱ	0.96 (7)	1.70 (7)	2.621 (4)	160 (6)

Symmetry code: (i) −x+1, −y, −z.

Acknowledgements

This work was supported by Fundação para a Ciência e a Tecnologia (FCT) under project POCI/FIS/57876/2004.

References

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