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Acta Crystallogr Sect E Struct Rep Online. 2008 July 1; 64(Pt 7): m962.
Published online 2008 June 25. doi:  10.1107/S1600536808018631
PMCID: PMC2961758

Dichlorido(methanol-κO)[2-(2-pyridyl­meth­oxy)-1,10-phenanthroline-κ3 N,N′,N′′]manganese(II)

Abstract

In the title mononuclear complex, [MnCl2(C18H13N3O)(CH4O)], the MnII ion assumes a distorted octa­hedral geometry. There is a π–π stacking inter­action between the phenanthroline ligand and the pyridine ring of a neighboring complex [centroid-to-centroid distance 3.5518 (13) Å]. The crystal structure also contains weak inter­molecular O—H(...)Cl hydrogen bonds that link neighboring complex mol­ecules into a one-dimensional chain along the b axis.

Related literature

For related structures, see: Liu et al. (2008 [triangle]); Li et al. (2008 [triangle]).

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Object name is e-64-0m962-scheme1.jpg

Experimental

Crystal data

  • [MnCl2(C18H13N3O)(CH4O)]
  • M r = 445.20
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m962-efi1.jpg
  • a = 10.0390 (16) Å
  • b = 13.667 (2) Å
  • c = 13.583 (2) Å
  • β = 92.874 (2)°
  • V = 1861.2 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.02 mm−1
  • T = 298 (2) K
  • 0.38 × 0.18 × 0.13 mm

Data collection

  • Bruker SMART APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2008 [triangle]) T min = 0.699, T max = 0.879
  • 10717 measured reflections
  • 4048 independent reflections
  • 3278 reflections with I > 2σ(I)
  • R int = 0.033

Refinement

  • R[F 2 > 2σ(F 2)] = 0.036
  • wR(F 2) = 0.090
  • S = 1.01
  • 4048 reflections
  • 245 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.28 e Å−3
  • Δρmin = −0.26 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808018631/bx2150sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808018631/bx2150Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

Derivatives of 1,10-phenanthroline play an important role in modern coordination chemistry and many complexes have been reported with different subsitituent groups (Li et al. 2008; Liu et al. 2008), but no complex with (pyridyl-2-yl)methoxy as substituent has been published. We report here the crystal structure of the title complex, Fig1.

Compound (I) is a monomer, in which the Mn atom adopts a distorted octahedral geometry completed by two N-atom donors from 1,10-phenanthroline, one N atom from pyridine ring, two Cl atom and one O atom from methanol molecule. In neighboring monomers, there is a strong π-π interaction between 1,10-phenanthroline ligand and pyridine ring with a centroid-to-centroid distance of 3.5518 (13) Å . In addition, the crystal structure contains O—H···Cl hydrogen bonds that made the neighboring complexes connect into a one-dimensional chain along b axis as shown in Fig. 2.

Experimental

10 ml methanol solution of (2-((pyridin-2-yl)methoxy)-1,10-phenanthroline (0.1200 g, 0.418 mmol) was added into 15 ml methanol solution of MnCl2.4H2O (0.0827 g, 0.418 mmol) and the mixture was stirred for a few minutes. The colorless single crystals were obtained after the filtrate had been allowed to stand at room temperature for a week.

Refinement

H atoms from the hydroxyl group of methanol was located in a difference Fourier map with O—H = 0.80 Å and refined as riding with Uiso(H) = 1.5Ueq(O); Other H atoms were placed in calculated positions with C—H = 0.96 Å for methyl group, C—H = 0.97 Å for methylene group and C—H = 0.93 Å for other H atoms, and refined as riding with Uiso(H) = 1.5Ueq(C) for methyl group and Uiso(H) = 1.2Ueq(C) for other H atoms.

Figures

Fig. 1.
Structure of the title complex with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
A view of the packing in the crystal structure. Intermolecular Hydrogen bonds as dashed lines.

Crystal data

[MnCl2(C18H13N3O)(CH4O)]F000 = 908
Mr = 445.20Dx = 1.589 Mg m3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3203 reflections
a = 10.0390 (16) Åθ = 2.5–25.7º
b = 13.667 (2) ŵ = 1.02 mm1
c = 13.583 (2) ÅT = 298 (2) K
β = 92.874 (2)ºBlock, colorless
V = 1861.2 (5) Å30.38 × 0.18 × 0.13 mm
Z = 4

Data collection

Bruker SMART APEX CCD diffractometer4048 independent reflections
Radiation source: fine-focus sealed tube3278 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.033
T = 298(2) Kθmax = 27.0º
[var phi] and ω scansθmin = 2.1º
Absorption correction: multi-scan(SADABS; Sheldrick, 2008)h = −12→12
Tmin = 0.699, Tmax = 0.879k = −13→17
10717 measured reflectionsl = −15→17

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036H-atom parameters constrained
wR(F2) = 0.090  w = 1/[σ2(Fo2) + (0.0466P)2] where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
4048 reflectionsΔρmax = 0.29 e Å3
245 parametersΔρmin = −0.25 e Å3
1 restraintExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

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)

xyzUiso*/Ueq
C10.1526 (2)0.79472 (15)0.58696 (17)0.0372 (5)
H10.09450.77460.63420.045*
C20.2736 (2)0.83666 (16)0.61481 (17)0.0409 (6)
H20.29880.84490.68110.049*
C30.3567 (2)0.86618 (16)0.54275 (17)0.0399 (5)
H30.43900.89440.55960.048*
C40.3163 (2)0.85338 (16)0.44621 (17)0.0373 (5)
H40.37260.87430.39810.045*
C50.1191 (2)0.78311 (14)0.48767 (16)0.0308 (5)
C6−0.01179 (19)0.73705 (16)0.45422 (16)0.0355 (5)
H6A−0.00340.70670.39030.043*
H6B−0.03490.68650.50050.043*
C7−0.1580 (2)0.84967 (15)0.36073 (17)0.0331 (5)
C8−0.2826 (2)0.89726 (17)0.36516 (18)0.0409 (6)
H8−0.32570.90100.42410.049*
C9−0.3375 (2)0.93711 (16)0.28180 (19)0.0420 (6)
H9−0.41950.96870.28290.050*
C10−0.2712 (2)0.93111 (14)0.19319 (18)0.0361 (5)
C11−0.14608 (19)0.88455 (14)0.19628 (16)0.0293 (5)
C12−0.3287 (2)0.96695 (16)0.1018 (2)0.0461 (6)
H12−0.41000.99960.10100.055*
C13−0.2673 (2)0.95437 (17)0.0167 (2)0.0476 (6)
H13−0.30790.9764−0.04220.057*
C14−0.1406 (2)0.90753 (15)0.01644 (17)0.0375 (5)
C15−0.0780 (2)0.87583 (14)0.10597 (16)0.0309 (5)
C16−0.0753 (3)0.88884 (18)−0.07041 (18)0.0499 (7)
H16−0.11470.9070−0.13110.060*
C170.0457 (3)0.84415 (18)−0.06574 (18)0.0474 (6)
H170.08910.8303−0.12300.057*
C180.1037 (2)0.81939 (16)0.02599 (17)0.0395 (5)
H180.18780.79070.02860.047*
C190.0884 (3)1.03698 (18)0.3451 (2)0.0593 (7)
H19A−0.00561.03890.32830.089*
H19B0.12451.10190.34190.089*
H19C0.10311.01170.41060.089*
Cl10.10996 (5)0.62442 (4)0.24263 (4)0.03925 (15)
Cl20.36834 (5)0.82286 (5)0.19848 (5)0.04570 (17)
Mn10.14453 (3)0.80494 (2)0.25537 (2)0.02795 (11)
N1−0.08860 (16)0.84415 (12)0.28120 (13)0.0288 (4)
N20.19883 (16)0.81198 (12)0.41697 (13)0.0314 (4)
N30.04509 (16)0.83459 (12)0.10973 (13)0.0304 (4)
O1−0.11631 (14)0.81011 (12)0.44771 (12)0.0424 (4)
O20.15254 (14)0.97535 (10)0.27729 (11)0.0372 (4)
H100.22271.00120.26760.056*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0430 (13)0.0372 (13)0.0317 (12)0.0068 (10)0.0055 (10)0.0042 (9)
C20.0529 (15)0.0374 (13)0.0315 (13)0.0060 (11)−0.0074 (11)−0.0010 (10)
C30.0361 (12)0.0417 (14)0.0408 (14)−0.0015 (10)−0.0076 (10)−0.0019 (10)
C40.0295 (11)0.0426 (13)0.0397 (14)−0.0022 (9)−0.0004 (10)0.0040 (10)
C50.0294 (11)0.0290 (11)0.0340 (12)0.0056 (8)0.0021 (9)0.0025 (9)
C60.0322 (11)0.0375 (12)0.0372 (13)0.0016 (9)0.0063 (9)0.0059 (10)
C70.0260 (10)0.0348 (12)0.0386 (13)−0.0033 (9)0.0006 (9)−0.0047 (9)
C80.0259 (11)0.0466 (14)0.0508 (15)0.0023 (10)0.0083 (10)−0.0090 (11)
C90.0253 (11)0.0357 (13)0.0647 (17)0.0054 (9)−0.0015 (11)−0.0082 (11)
C100.0283 (11)0.0253 (11)0.0539 (15)0.0003 (9)−0.0058 (10)−0.0022 (10)
C110.0261 (10)0.0225 (10)0.0389 (13)−0.0022 (8)−0.0037 (9)−0.0016 (8)
C120.0345 (12)0.0364 (13)0.0657 (18)0.0071 (10)−0.0153 (12)0.0040 (12)
C130.0455 (14)0.0414 (14)0.0538 (17)0.0008 (11)−0.0184 (12)0.0109 (11)
C140.0389 (12)0.0306 (11)0.0420 (14)−0.0058 (10)−0.0092 (10)0.0066 (10)
C150.0290 (11)0.0253 (11)0.0376 (13)−0.0056 (8)−0.0043 (9)0.0005 (9)
C160.0564 (16)0.0565 (16)0.0355 (15)−0.0093 (13)−0.0107 (12)0.0141 (11)
C170.0545 (16)0.0569 (16)0.0309 (13)−0.0074 (13)0.0024 (11)0.0023 (11)
C180.0364 (12)0.0465 (14)0.0356 (13)−0.0016 (10)0.0030 (10)−0.0020 (10)
C190.0622 (17)0.0401 (15)0.078 (2)−0.0018 (12)0.0270 (15)−0.0142 (13)
Cl10.0355 (3)0.0310 (3)0.0508 (4)0.0014 (2)−0.0029 (2)−0.0018 (2)
Cl20.0283 (3)0.0637 (4)0.0460 (4)−0.0058 (3)0.0106 (2)−0.0148 (3)
Mn10.02338 (17)0.03248 (19)0.02796 (19)0.00096 (12)0.00103 (13)−0.00058 (13)
N10.0243 (9)0.0298 (9)0.0322 (10)0.0001 (7)−0.0003 (7)−0.0021 (7)
N20.0266 (9)0.0361 (10)0.0313 (10)−0.0010 (7)0.0000 (8)0.0022 (7)
N30.0273 (9)0.0324 (10)0.0312 (10)−0.0013 (7)−0.0004 (7)0.0011 (7)
O10.0303 (8)0.0628 (11)0.0345 (9)0.0104 (7)0.0074 (7)0.0018 (7)
O20.0357 (8)0.0323 (8)0.0443 (9)−0.0042 (6)0.0076 (7)−0.0018 (7)

Geometric parameters (Å, °)

C1—C21.379 (3)C12—C131.347 (3)
C1—C51.382 (3)C12—H120.9300
C1—H10.9300C13—C141.424 (3)
C2—C31.377 (3)C13—H130.9300
C2—H20.9300C14—C161.402 (3)
C3—C41.364 (3)C14—C151.409 (3)
C3—H30.9300C15—N31.357 (3)
C4—N21.350 (3)C16—C171.358 (3)
C4—H40.9300C16—H160.9300
C5—N21.340 (3)C17—C181.390 (3)
C5—C61.507 (3)C17—H170.9300
C6—O11.448 (2)C18—N31.323 (3)
C6—H6A0.9700C18—H180.9300
C6—H6B0.9700C19—O21.425 (3)
C7—N11.316 (3)C19—H19A0.9600
C7—O11.347 (3)C19—H19B0.9600
C7—C81.414 (3)C19—H19C0.9600
C8—C91.349 (3)Cl1—Mn12.4961 (7)
C8—H80.9300Cl2—Mn12.4248 (7)
C9—C101.407 (3)Mn1—N32.2082 (18)
C9—H90.9300Mn1—N22.2370 (18)
C10—C111.407 (3)Mn1—O22.3487 (14)
C10—C121.430 (3)Mn1—N12.4434 (17)
C11—N11.379 (3)O2—H100.8048
C11—C151.439 (3)
C2—C1—C5118.9 (2)N3—C15—C11118.23 (18)
C2—C1—H1120.6C14—C15—C11119.99 (19)
C5—C1—H1120.6C17—C16—C14119.8 (2)
C3—C2—C1118.9 (2)C17—C16—H16120.1
C3—C2—H2120.6C14—C16—H16120.1
C1—C2—H2120.6C16—C17—C18119.0 (2)
C4—C3—C2119.0 (2)C16—C17—H17120.5
C4—C3—H3120.5C18—C17—H17120.5
C2—C3—H3120.5N3—C18—C17123.2 (2)
N2—C4—C3123.3 (2)N3—C18—H18118.4
N2—C4—H4118.3C17—C18—H18118.4
C3—C4—H4118.3O2—C19—H19A109.5
N2—C5—C1122.74 (19)O2—C19—H19B109.5
N2—C5—C6116.75 (19)H19A—C19—H19B109.5
C1—C5—C6120.5 (2)O2—C19—H19C109.5
O1—C6—C5110.41 (17)H19A—C19—H19C109.5
O1—C6—H6A109.6H19B—C19—H19C109.5
C5—C6—H6A109.6N3—Mn1—N2161.46 (6)
O1—C6—H6B109.6N3—Mn1—O286.71 (6)
C5—C6—H6B109.6N2—Mn1—O280.09 (6)
H6A—C6—H6B108.1N3—Mn1—Cl294.62 (5)
N1—C7—O1122.89 (18)N2—Mn1—Cl297.14 (5)
N1—C7—C8124.5 (2)O2—Mn1—Cl285.06 (4)
O1—C7—C8112.6 (2)N3—Mn1—N172.25 (6)
C9—C8—C7118.4 (2)N2—Mn1—N192.16 (6)
C9—C8—H8120.8O2—Mn1—N177.95 (5)
C7—C8—H8120.8Cl2—Mn1—N1158.93 (5)
C8—C9—C10120.2 (2)N3—Mn1—Cl193.68 (5)
C8—C9—H9119.9N2—Mn1—Cl197.86 (5)
C10—C9—H9119.9O2—Mn1—Cl1173.00 (4)
C11—C10—C9117.5 (2)Cl2—Mn1—Cl1101.86 (2)
C11—C10—C12120.1 (2)N1—Mn1—Cl195.50 (4)
C9—C10—C12122.4 (2)C7—N1—C11116.55 (17)
N1—C11—C10122.8 (2)C7—N1—Mn1132.87 (14)
N1—C11—C15118.89 (17)C11—N1—Mn1109.35 (13)
C10—C11—C15118.28 (19)C5—N2—C4117.19 (19)
C13—C12—C10121.3 (2)C5—N2—Mn1124.45 (13)
C13—C12—H12119.4C4—N2—Mn1118.23 (14)
C10—C12—H12119.4C18—N3—C15118.45 (19)
C12—C13—C14120.5 (2)C18—N3—Mn1122.74 (14)
C12—C13—H13119.8C15—N3—Mn1118.68 (14)
C14—C13—H13119.8C7—O1—C6121.52 (17)
C16—C14—C15117.6 (2)C19—O2—Mn1130.86 (14)
C16—C14—C13122.7 (2)C19—O2—H10105.9
C15—C14—C13119.7 (2)Mn1—O2—H10116.0
N3—C15—C14121.8 (2)
C5—C1—C2—C30.5 (3)Cl1—Mn1—N1—C787.71 (18)
C1—C2—C3—C40.3 (3)N3—Mn1—N1—C11−13.64 (12)
C2—C3—C4—N2−0.8 (3)N2—Mn1—N1—C11156.13 (12)
C2—C1—C5—N2−0.8 (3)O2—Mn1—N1—C1176.75 (12)
C2—C1—C5—C6179.61 (19)Cl2—Mn1—N1—C1139.8 (2)
N2—C5—C6—O1−93.6 (2)Cl1—Mn1—N1—C11−105.76 (12)
C1—C5—C6—O186.0 (2)C1—C5—N2—C40.4 (3)
N1—C7—C8—C92.4 (3)C6—C5—N2—C4179.96 (18)
O1—C7—C8—C9−177.8 (2)C1—C5—N2—Mn1−175.49 (14)
C7—C8—C9—C10−0.1 (3)C6—C5—N2—Mn14.1 (2)
C8—C9—C10—C11−1.4 (3)C3—C4—N2—C50.4 (3)
C8—C9—C10—C12176.2 (2)C3—C4—N2—Mn1176.55 (17)
C9—C10—C11—N11.0 (3)N3—Mn1—N2—C567.7 (3)
C12—C10—C11—N1−176.65 (18)O2—Mn1—N2—C5112.92 (16)
C9—C10—C11—C15178.68 (18)Cl2—Mn1—N2—C5−163.39 (15)
C12—C10—C11—C151.0 (3)N1—Mn1—N2—C535.55 (16)
C11—C10—C12—C132.2 (3)Cl1—Mn1—N2—C5−60.30 (16)
C9—C10—C12—C13−175.4 (2)N3—Mn1—N2—C4−108.1 (2)
C10—C12—C13—C14−2.1 (3)O2—Mn1—N2—C4−62.89 (15)
C12—C13—C14—C16177.1 (2)Cl2—Mn1—N2—C420.79 (15)
C12—C13—C14—C15−1.2 (3)N1—Mn1—N2—C4−140.26 (15)
C16—C14—C15—N34.4 (3)Cl1—Mn1—N2—C4123.88 (15)
C13—C14—C15—N3−177.20 (19)C17—C18—N3—C150.4 (3)
C16—C14—C15—C11−174.03 (19)C17—C18—N3—Mn1−175.35 (17)
C13—C14—C15—C114.4 (3)C14—C15—N3—C18−3.7 (3)
N1—C11—C15—N3−4.9 (3)C11—C15—N3—C18174.77 (18)
C10—C11—C15—N3177.29 (17)C14—C15—N3—Mn1172.26 (14)
N1—C11—C15—C14173.53 (17)C11—C15—N3—Mn1−9.3 (2)
C10—C11—C15—C14−4.2 (3)N2—Mn1—N3—C18154.10 (19)
C15—C14—C16—C17−1.8 (3)O2—Mn1—N3—C18109.61 (17)
C13—C14—C16—C17179.8 (2)Cl2—Mn1—N3—C1824.84 (16)
C14—C16—C17—C18−1.2 (4)N1—Mn1—N3—C18−172.00 (18)
C16—C17—C18—N32.0 (4)Cl1—Mn1—N3—C18−77.39 (16)
O1—C7—N1—C11177.43 (18)N2—Mn1—N3—C15−21.6 (3)
C8—C7—N1—C11−2.8 (3)O2—Mn1—N3—C15−66.13 (14)
O1—C7—N1—Mn1−16.8 (3)Cl2—Mn1—N3—C15−150.90 (14)
C8—C7—N1—Mn1162.96 (16)N1—Mn1—N3—C1512.26 (13)
C10—C11—N1—C71.1 (3)Cl1—Mn1—N3—C15106.87 (14)
C15—C11—N1—C7−176.61 (17)N1—C7—O1—C6−16.9 (3)
C10—C11—N1—Mn1−167.94 (15)C8—C7—O1—C6163.28 (18)
C15—C11—N1—Mn114.4 (2)C5—C6—O1—C7100.3 (2)
N3—Mn1—N1—C7179.82 (19)N3—Mn1—O2—C19114.2 (2)
N2—Mn1—N1—C7−10.41 (18)N2—Mn1—O2—C19−52.8 (2)
O2—Mn1—N1—C7−89.79 (18)Cl2—Mn1—O2—C19−150.9 (2)
Cl2—Mn1—N1—C7−126.75 (17)N1—Mn1—O2—C1941.6 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H10···Cl1i0.802.393.1581 (16)161

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BX2150).

References

  • Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Li, H. L. & Liu, Q. S. (2008). Acta Cryst. E64, m847. [PMC free article] [PubMed]
  • Liu, Q. S., Liu, L. D. & Shi, J. M. (2008). Acta Cryst. C64, m58–m60. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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