Literature DB >> 21200595

(Benzoato-κO,O')(quinoline-2-carboxyl-ato-κN,O)(quinoline-2-carboxylic acid-κN,O)manganese(II).

Nuno D Martins, Joana A Silva, Manuela Ramos Silva, Ana Matos Beja, Abilio J F N Sobral.   

Abstract

The crystal structure of the title compound, [Mn(C(7)H(5)O(2))(C(10)H(6)NO(2))(C(10)H(7)NO(2))], contains manganese(II) ions six-coordinated in a distorted octa-hedral environment. The equatorial plane is occupied by four O atoms, two from the carboxyl-ate group of the benzoate ion, the other two from carboxyl-ate/carboxyl groups of the quinaldate/quinaldic acid mol-ecules. 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 carboxyl-ate/carboxyl groups of adjacent quinaldate/quinaldic acid mol-ecules, forming zigzag chains that run along the c axis.

Entities:  

Year:  2007        PMID： 21200595      PMCID： PMC2915171          DOI： 10.1107/S1600536807066809

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


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 = 521.37 Monoclinic, 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[F 2 > 2σ(F 2)] = 0.048 wR(F 2) = 0.149 S = 1.08 2917 reflections 169 parameters 1 restraint H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.68 e Å−3 Δρmin = −0.50 e Å−3 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. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807066809/bt2660sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536807066809/bt2660Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Mn(C7H5O2)(C10H6NO2)(C10H7NO2)]F000 = 1068
Mr = 521.37Dx = 1.480 Mg m−3
Monoclinic, C2/cMo Kα radiation λ = 0.71073 Å
a = 19.3839 (4) ÅCell parameters from 8901 reflections
b = 11.6775 (2) Åθ = 2.4–27.5º
c = 11.6306 (2) ŵ = 0.61 mm−1
β = 117.2880 (10)ºT = 293 (2) K
V = 2339.67 (8) Å3Prism, pink
Z = 40.24 × 0.22 × 0.15 mm
Bruker APEX CCD area-detector diffractometer2917 independent reflections
Radiation source: fine-focus sealed tube2413 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.027
T = 293(2) Kθmax = 28.4º
φ and ω scansθmin = 2.1º
Absorption correction: multi-scan(SADABS; Sheldrick, 2000)h = −25→25
Tmin = 0.883, Tmax = 0.908k = −15→15
25798 measured reflectionsl = −15→15
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.149  w = 1/[σ2(Fo2) + (0.0806P)2 + 2.8119P] where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
2917 reflectionsΔρmax = 0.68 e Å−3
169 parametersΔρmin = −0.50 e Å−3
1 restraintExtinction correction: none
Primary atom site location: structure-invariant direct methods
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.
xyzUiso*/UeqOcc. (<1)
Mn10.50000.20556 (4)0.25000.03799 (18)
O10.48852 (12)0.37094 (15)0.14858 (17)0.0505 (4)
O20.48495 (10)0.09330 (17)0.09597 (18)0.0508 (5)
H20.525 (3)0.041 (5)0.103 (7)0.07 (2)*0.50
N10.37188 (11)0.15467 (17)0.15100 (18)0.0378 (4)
C10.50000.4239 (3)0.25000.0395 (7)
C20.50000.5526 (3)0.25000.0359 (6)
C30.48852 (16)0.6123 (2)0.1396 (2)0.0457 (6)
H30.48070.57280.06520.055*
C40.4888 (2)0.7302 (3)0.1403 (3)0.0569 (7)
H40.48130.77020.06640.068*
C50.50000.7889 (3)0.25000.0582 (10)
H50.50000.86850.25000.070*
C60.41618 (15)0.0511 (3)0.0173 (3)0.0521 (6)
O30.39792 (16)0.0125 (4)−0.0885 (3)0.1252 (15)
C70.35213 (13)0.0869 (2)0.0500 (2)0.0402 (5)
C150.31580 (14)0.1843 (2)0.1866 (2)0.0418 (5)
C100.23875 (14)0.1435 (2)0.1169 (3)0.0487 (6)
C90.22055 (15)0.0739 (3)0.0085 (3)0.0553 (7)
H90.17010.0476−0.04040.066*
C80.27651 (15)0.0452 (2)−0.0249 (3)0.0501 (6)
H80.2652−0.0014−0.09630.060*
C110.18377 (18)0.1752 (3)0.1597 (4)0.0668 (9)
H110.13270.15000.11480.080*
C120.2053 (2)0.2419 (4)0.2655 (4)0.0790 (11)
H120.16900.26080.29380.095*
C130.2808 (2)0.2828 (3)0.3327 (3)0.0710 (9)
H130.29420.32920.40490.085*
C140.33583 (17)0.2557 (3)0.2942 (3)0.0551 (7)
H140.38600.28440.33890.066*
U11U22U33U12U13U23
Mn10.0367 (3)0.0369 (3)0.0406 (3)0.0000.0179 (2)0.000
O10.0663 (12)0.0394 (9)0.0450 (9)−0.0012 (8)0.0248 (9)−0.0037 (7)
O20.0375 (9)0.0580 (11)0.0577 (10)−0.0023 (8)0.0226 (8)−0.0194 (9)
N10.0344 (9)0.0405 (10)0.0380 (9)0.0031 (8)0.0162 (8)0.0023 (8)
C10.0338 (15)0.0405 (16)0.0427 (16)0.0000.0161 (13)0.000
C20.0321 (14)0.0367 (16)0.0402 (15)0.0000.0178 (12)0.000
C30.0552 (14)0.0469 (13)0.0379 (11)−0.0038 (11)0.0238 (11)−0.0019 (10)
C40.076 (2)0.0496 (15)0.0481 (14)−0.0032 (14)0.0305 (14)0.0087 (12)
C50.075 (3)0.0352 (18)0.065 (2)0.0000.033 (2)0.000
C60.0408 (13)0.0669 (17)0.0482 (13)0.0026 (12)0.0201 (11)−0.0100 (13)
O30.0565 (15)0.199 (4)0.117 (2)−0.0191 (18)0.0365 (15)−0.111 (3)
C70.0346 (11)0.0402 (12)0.0432 (12)0.0024 (9)0.0157 (9)0.0034 (10)
C150.0360 (11)0.0464 (13)0.0440 (12)0.0093 (9)0.0193 (10)0.0103 (10)
C100.0340 (12)0.0548 (15)0.0575 (15)0.0096 (11)0.0211 (11)0.0161 (12)
C90.0345 (12)0.0608 (16)0.0625 (16)−0.0049 (11)0.0152 (11)0.0050 (14)
C80.0415 (13)0.0508 (14)0.0497 (14)−0.0044 (11)0.0137 (11)−0.0047 (12)
C110.0428 (15)0.088 (2)0.078 (2)0.0158 (15)0.0348 (15)0.0171 (18)
C120.064 (2)0.105 (3)0.088 (2)0.033 (2)0.0518 (19)0.018 (2)
C130.069 (2)0.089 (3)0.0659 (19)0.0200 (18)0.0405 (17)−0.0030 (17)
C140.0501 (15)0.0647 (17)0.0522 (15)0.0115 (13)0.0249 (13)−0.0014 (13)
Mn1—O2i2.1293 (18)C5—C4i1.375 (3)
Mn1—O22.1293 (18)C5—H50.9300
Mn1—O1i2.2203 (19)C6—O31.200 (4)
Mn1—O12.2203 (19)C6—C71.515 (3)
Mn1—N12.2858 (19)C7—C81.405 (3)
Mn1—N1i2.2858 (19)C15—C141.401 (4)
Mn1—C12.550 (3)C15—C101.416 (4)
O1—C11.258 (2)C10—C91.403 (4)
O2—C61.319 (3)C10—C111.416 (4)
O2—H20.959 (10)C9—C81.352 (4)
N1—C71.319 (3)C9—H90.9300
N1—C151.373 (3)C8—H80.9300
C1—O1i1.258 (2)C11—C121.350 (6)
C1—C21.503 (5)C11—H110.9300
C2—C31.386 (3)C12—C131.390 (6)
C2—C3i1.386 (3)C12—H120.9300
C3—C41.377 (4)C13—C141.370 (4)
C3—H30.9300C13—H130.9300
C4—C51.375 (3)C14—H140.9300
C4—H40.9300
O2i—Mn1—O2104.00 (12)C4—C3—H3120.0
O2i—Mn1—O1i98.44 (7)C2—C3—H3120.0
O2—Mn1—O1i157.55 (8)C5—C4—C3120.2 (3)
O2i—Mn1—O1157.55 (8)C5—C4—H4119.9
O2—Mn1—O198.44 (7)C3—C4—H4119.9
O1i—Mn1—O159.13 (9)C4—C5—C4i120.2 (4)
O2i—Mn1—N187.81 (7)C4—C5—H5119.9
O2—Mn1—N173.62 (7)C4i—C5—H5119.9
O1i—Mn1—N1108.35 (7)O3—C6—O2125.5 (3)
O1—Mn1—N197.90 (7)O3—C6—C7118.1 (2)
O2i—Mn1—N1i73.62 (7)O2—C6—C7114.0 (2)
O2—Mn1—N1i87.81 (7)N1—C7—C8123.7 (2)
O1i—Mn1—N1i97.90 (7)N1—C7—C6116.9 (2)
O1—Mn1—N1i108.35 (7)C8—C7—C6119.3 (2)
N1—Mn1—N1i149.86 (10)N1—C15—C14119.0 (2)
O2i—Mn1—C1128.00 (6)N1—C15—C10121.0 (2)
O2—Mn1—C1128.00 (6)C14—C15—C10119.9 (2)
O1i—Mn1—C129.57 (4)C9—C10—C15118.3 (2)
O1—Mn1—C129.57 (5)C9—C10—C11123.2 (3)
N1—Mn1—C1105.07 (5)C15—C10—C11118.5 (3)
N1i—Mn1—C1105.07 (5)C8—C9—C10119.9 (2)
C1—O1—Mn189.89 (16)C8—C9—H9120.1
C6—O2—Mn1121.28 (15)C10—C9—H9120.1
C6—O2—H2110 (4)C9—C8—C7118.8 (3)
Mn1—O2—H2122 (4)C9—C8—H8120.6
C7—N1—C15118.2 (2)C7—C8—H8120.6
C7—N1—Mn1114.17 (15)C12—C11—C10120.1 (3)
C15—N1—Mn1127.58 (16)C12—C11—H11119.9
O1—C1—O1i121.1 (3)C10—C11—H11119.9
O1—C1—C2119.46 (16)C11—C12—C13121.2 (3)
O1i—C1—C2119.46 (16)C11—C12—H12119.4
O1—C1—Mn160.54 (16)C13—C12—H12119.4
O1i—C1—Mn160.54 (16)C14—C13—C12120.8 (3)
C2—C1—Mn1180.0C14—C13—H13119.6
C3—C2—C3i119.6 (3)C12—C13—H13119.6
C3—C2—C1120.20 (16)C13—C14—C15119.4 (3)
C3i—C2—C1120.20 (16)C13—C14—H14120.3
C4—C3—C2119.9 (2)C15—C14—H14120.3
O2i—Mn1—O1—C13.1 (2)O1—C1—C2—C3−0.90 (17)
O2—Mn1—O1—C1−178.80 (10)O1i—C1—C2—C3179.10 (17)
O1i—Mn1—O1—C10.0Mn1—C1—C2—C3−108 (100)
N1—Mn1—O1—C1106.70 (10)O1—C1—C2—C3i179.10 (17)
N1i—Mn1—O1—C1−88.30 (11)O1i—C1—C2—C3i−0.90 (17)
O2i—Mn1—O2—C685.4 (2)Mn1—C1—C2—C3i72 (100)
O1i—Mn1—O2—C6−96.5 (3)C3i—C2—C3—C40.2 (2)
O1—Mn1—O2—C6−93.8 (2)C1—C2—C3—C4−179.8 (2)
N1—Mn1—O2—C62.0 (2)C2—C3—C4—C5−0.3 (4)
N1i—Mn1—O2—C6157.9 (2)C3—C4—C5—C4i0.2 (2)
C1—Mn1—O2—C6−94.6 (2)Mn1—O2—C6—O3160.0 (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—C81.4 (4)
O1i—Mn1—N1—C7154.79 (16)Mn1—N1—C7—C8179.9 (2)
O1—Mn1—N1—C794.77 (17)C15—N1—C7—C6−177.1 (2)
N1i—Mn1—N1—C7−55.92 (15)Mn1—N1—C7—C61.5 (3)
C1—Mn1—N1—C7124.07 (15)O3—C6—C7—N1−163.2 (3)
O2i—Mn1—N1—C1571.34 (19)O2—C6—C7—N10.1 (4)
O2—Mn1—N1—C15176.6 (2)O3—C6—C7—C818.3 (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—C14179.6 (2)
N1i—Mn1—N1—C15122.46 (19)Mn1—N1—C15—C141.3 (3)
C1—Mn1—N1—C15−57.55 (19)C7—N1—C15—C10−0.1 (3)
Mn1—O1—C1—O1i0.000 (1)Mn1—N1—C15—C10−178.43 (17)
Mn1—O1—C1—C2180.0N1—C15—C10—C9−1.4 (4)
O2i—Mn1—C1—O1−178.49 (12)C14—C15—C10—C9178.9 (3)
O2—Mn1—C1—O11.51 (12)N1—C15—C10—C11178.8 (2)
O1i—Mn1—C1—O1180.0C14—C15—C10—C11−0.9 (4)
N1—Mn1—C1—O1−79.27 (12)C15—C10—C9—C81.7 (4)
N1i—Mn1—C1—O1100.73 (12)C11—C10—C9—C8−178.6 (3)
O2i—Mn1—C1—O1i1.51 (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—O1i180.000 (1)C6—C7—C8—C9177.3 (3)
N1—Mn1—C1—O1i100.73 (12)C9—C10—C11—C12179.6 (3)
N1i—Mn1—C1—O1i−79.27 (12)C15—C10—C11—C12−0.7 (5)
O2i—Mn1—C1—C2−72 (100)C10—C11—C12—C131.4 (6)
O2—Mn1—C1—C2108 (100)C11—C12—C13—C14−0.6 (6)
O1i—Mn1—C1—C2−73 (100)C12—C13—C14—C15−1.0 (5)
O1—Mn1—C1—C2107 (100)N1—C15—C14—C13−178.0 (3)
N1—Mn1—C1—C228 (100)C10—C15—C14—C131.7 (4)
N1i—Mn1—C1—C2−152 (100)
D—H···AD—HH···AD···AD—H···A
O2—H2···O3ii0.96 (7)1.70 (7)2.621 (4)160 (6)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O2—H2⋯O3i0.96 (7)1.70 (7)2.621 (4)160 (6)

Symmetry code: (i) .

  1 in total

1.  (Benzoato-κO,O')(quinoline-2-carboxyl-ato-κN,O)(quinoline-2-carboxylic acid-κN,O)copper(II).

Authors:  Nuno D Martins; Manuela Ramos Silva; Joana A Silva; Ana Matos Beja; Abilio J F N Sobral
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-05-21
  1 in total

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