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Acta Crystallogr Sect E Struct Rep Online. 2009 October 1; 65(Pt 10): o2549.
Published online 2009 September 26. doi:  10.1107/S1600536809038318
PMCID: PMC2970499

2,9-Bis(4-pyridylmeth­oxy)-1,10-phenanthroline

Abstract

In the title mol­ecule, C24H18N4O2, the dihedral angles between the mean plane of the phenanthroline ring system and the pyridine rings are 82.52 (5) and 71.58 (4)°. The dihedral angle between the two pyridine ring planes is 53.54 (6)°. In the crystal structure, there are π–π stacking inter­actions between 1,10-phenanthroline rings, with centroid–centroid distances of 3.6101 (11) and 3.5864 (11) Å.

Related literature

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

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Object name is e-65-o2549-scheme1.jpg

Experimental

Crystal data

  • C24H18N4O2
  • M r = 394.42
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2549-efi1.jpg
  • a = 12.701 (2) Å
  • b = 16.418 (3) Å
  • c = 9.7443 (16) Å
  • β = 107.535 (2)°
  • V = 1937.5 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 298 K
  • 0.51 × 0.40 × 0.38 mm

Data collection

  • Bruker SMART APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.956, T max = 0.967
  • 9860 measured reflections
  • 3530 independent reflections
  • 2603 reflections with I > 2σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.043
  • wR(F 2) = 0.113
  • S = 1.03
  • 3530 reflections
  • 271 parameters
  • H-atom parameters constrained
  • Δρmax = 0.13 e Å−3
  • Δρmin = −0.16 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.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809038318/lh2907sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809038318/lh2907Isup2.hkl

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

Acknowledgments

The authors thank the Project of Scientific Studies Development of Shandong Provincial Education Department (grant No. J08LC51) and the Natural Science Foundation of Shandong Province of China (grant No. Y2007B26).

supplementary crystallographic information

Comment

Derivatives of 1,10-phenanthroline play an important role in modern coordination chemistry and a number of the derivatives (e.g. Liu et al., 2008; Zhang et al. 2008) have been synthesized and used as ligands to prepare new complexes. Herein we report the crystal structure of the title compound.

The molecular structure is shown in Fig. 1. There are two π–π stacking interactions involving 1,10-phenathroline ring systems, one involving symmetry related pyridine rings with the relevant distances being Cg1···Cg2i = 3.6101 (11) Å and Cg1···Cg2iperp = 3.373 Å and α = 1.63°; another from the adjacent pyridine rings and the benzene rings with the relevant distances being Cg2···Cg3i = 3.5864 (11) Å and Cg2···Cg3iperp = 3.383 Å and α = 1.29° [symmetry code: (i) 1 - x, -y, 1 - z; Cg1, Cg2 and Cg3 are the centroids of C1—C5/N3 ring, C8—C12/N4 ring and C4—C9 ring, respectively; Cgi···Cgjperp is the perpendicular distance from ring Cgi to ring Cgji; α is the dihedral angle between ring plane Cgi and ring plane Cgji].

Experimental

Powdered 2,9-Bis((pyridin-4-yl)methoxy)-1,10-phenanthroline (0.1025 g, 0.260 mmol) was dissolved in 15 ml methanol and yellow single crystals were obtained after the filtrate had been allowed to stand at room temperature for four weeks.

Refinement

All H atoms were placed in calculated positions and refined as riding with C—H = 0.97 Å for methylene groups and C—H = 0.93 Å for other H atoms and with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
Molecular structure of title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

Crystal data

C24H18N4O2F(000) = 824
Mr = 394.42Dx = 1.352 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2776 reflections
a = 12.701 (2) Åθ = 2.5–25.2°
b = 16.418 (3) ŵ = 0.09 mm1
c = 9.7443 (16) ÅT = 298 K
β = 107.535 (2)°Block, yellow
V = 1937.5 (6) Å30.51 × 0.40 × 0.38 mm
Z = 4

Data collection

Bruker SMART APEX CCD diffractometer3530 independent reflections
Radiation source: fine-focus sealed tube2603 reflections with I > 2σ(I)
graphiteRint = 0.028
[var phi] and ω scansθmax = 25.3°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −15→11
Tmin = 0.956, Tmax = 0.967k = −14→19
9860 measured reflectionsl = −10→11

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0569P)2 + 0.0745P] where P = (Fo2 + 2Fc2)/3
3530 reflections(Δ/σ)max = 0.002
271 parametersΔρmax = 0.13 e Å3
0 restraintsΔρmin = −0.16 e Å3

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
C10.50194 (13)0.23897 (10)0.53260 (16)0.0523 (4)
C20.61170 (14)0.25413 (11)0.53679 (18)0.0622 (5)
H20.64880.30030.58190.075*
C30.66137 (14)0.19987 (12)0.47360 (18)0.0626 (5)
H30.73390.20850.47430.075*
C40.60421 (12)0.12976 (10)0.40609 (16)0.0524 (4)
C50.49508 (11)0.12005 (9)0.40882 (14)0.0449 (4)
C60.65165 (13)0.07031 (12)0.33719 (18)0.0643 (5)
H60.72390.07690.33530.077*
C70.59392 (14)0.00485 (12)0.27477 (19)0.0646 (5)
H70.6268−0.03330.23010.078*
C80.43337 (11)0.04990 (9)0.34246 (15)0.0441 (4)
C90.48333 (12)−0.00739 (10)0.27554 (16)0.0516 (4)
C100.42012 (14)−0.07576 (11)0.21217 (17)0.0600 (4)
H100.4501−0.11460.16530.072*
C110.31631 (14)−0.08512 (10)0.21916 (17)0.0579 (4)
H110.2737−0.13000.17800.069*
C120.27507 (12)−0.02471 (10)0.29082 (16)0.0486 (4)
C130.12405 (13)0.01882 (12)0.37343 (18)0.0623 (5)
H13A0.18290.04880.44130.075*
H13B0.0830−0.01000.42760.075*
C140.04897 (11)0.07741 (10)0.27374 (18)0.0542 (4)
C150.03967 (13)0.08218 (11)0.12927 (18)0.0610 (5)
H150.08320.04920.09060.073*
C16−0.03412 (15)0.13578 (12)0.0426 (2)0.0752 (5)
H16−0.03890.1373−0.05450.090*
C17−0.01738 (13)0.12956 (12)0.3232 (2)0.0675 (5)
H17−0.01410.12960.41990.081*
C18−0.08782 (15)0.18100 (14)0.2280 (3)0.0829 (6)
H18−0.13130.21550.26390.100*
C190.26496 (12)0.31914 (10)0.46362 (16)0.0526 (4)
C200.13577 (17)0.31235 (18)0.2316 (2)0.0918 (7)
H200.09680.28030.15420.110*
C210.20466 (15)0.27345 (13)0.34918 (19)0.0721 (5)
H210.21030.21700.35120.087*
C220.17931 (16)0.43588 (14)0.3319 (2)0.0781 (6)
H220.17100.49220.32810.094*
C230.25156 (14)0.40236 (12)0.4528 (2)0.0636 (5)
H230.29140.43580.52750.076*
C240.34284 (14)0.28164 (11)0.59467 (17)0.0622 (5)
H24A0.33050.30510.67990.075*
H24B0.32880.22360.59500.075*
N1−0.09879 (13)0.18537 (11)0.0876 (2)0.0860 (5)
N20.12073 (13)0.39253 (15)0.2202 (2)0.0891 (6)
N30.44458 (9)0.17568 (8)0.47191 (12)0.0472 (3)
N40.32756 (9)0.04086 (7)0.34768 (12)0.0455 (3)
O10.17152 (8)−0.03913 (7)0.29945 (12)0.0615 (3)
O20.45550 (9)0.29496 (7)0.59879 (12)0.0660 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0513 (9)0.0475 (10)0.0472 (9)−0.0005 (8)−0.0017 (7)0.0046 (8)
C20.0538 (10)0.0537 (11)0.0650 (11)−0.0114 (8)−0.0031 (8)0.0087 (9)
C30.0434 (9)0.0704 (12)0.0662 (11)−0.0102 (9)0.0049 (8)0.0173 (10)
C40.0418 (8)0.0599 (11)0.0521 (9)−0.0008 (8)0.0091 (7)0.0135 (8)
C50.0419 (8)0.0474 (9)0.0402 (8)0.0014 (7)0.0043 (6)0.0088 (7)
C60.0431 (9)0.0840 (14)0.0664 (11)0.0034 (9)0.0176 (8)0.0102 (10)
C70.0553 (10)0.0762 (13)0.0658 (11)0.0124 (10)0.0234 (8)−0.0016 (9)
C80.0400 (8)0.0485 (9)0.0401 (8)0.0042 (7)0.0064 (6)0.0061 (7)
C90.0500 (9)0.0556 (10)0.0473 (9)0.0088 (8)0.0118 (7)0.0023 (8)
C100.0637 (11)0.0539 (11)0.0575 (10)0.0119 (8)0.0109 (8)−0.0084 (8)
C110.0591 (10)0.0460 (10)0.0590 (10)0.0009 (8)0.0032 (8)−0.0056 (8)
C120.0421 (8)0.0457 (9)0.0513 (9)−0.0006 (7)0.0038 (7)0.0036 (7)
C130.0459 (9)0.0767 (12)0.0654 (10)−0.0077 (9)0.0185 (8)−0.0004 (9)
C140.0365 (8)0.0619 (11)0.0620 (10)−0.0109 (7)0.0114 (7)−0.0110 (8)
C150.0481 (9)0.0693 (12)0.0631 (11)0.0026 (8)0.0130 (8)−0.0089 (9)
C160.0634 (11)0.0867 (15)0.0662 (11)0.0084 (11)0.0054 (9)−0.0062 (11)
C170.0475 (10)0.0841 (14)0.0718 (11)−0.0079 (9)0.0192 (9)−0.0200 (10)
C180.0513 (11)0.0878 (16)0.1067 (18)0.0102 (10)0.0193 (11)−0.0274 (13)
C190.0510 (9)0.0587 (11)0.0521 (9)−0.0031 (8)0.0216 (7)−0.0066 (8)
C200.0708 (14)0.122 (2)0.0703 (13)−0.0159 (13)0.0028 (10)−0.0075 (14)
C210.0717 (12)0.0748 (13)0.0633 (11)−0.0110 (10)0.0107 (9)−0.0086 (10)
C220.0615 (12)0.0805 (14)0.1001 (16)0.0159 (11)0.0363 (12)0.0180 (13)
C230.0602 (10)0.0630 (12)0.0709 (11)0.0037 (9)0.0246 (9)−0.0052 (9)
C240.0737 (12)0.0593 (11)0.0532 (10)−0.0022 (9)0.0184 (8)−0.0102 (8)
N10.0628 (10)0.0889 (13)0.0937 (13)0.0183 (9)0.0047 (9)−0.0108 (10)
N20.0573 (10)0.1221 (17)0.0853 (12)0.0093 (11)0.0178 (9)0.0238 (13)
N30.0450 (7)0.0455 (8)0.0446 (7)−0.0008 (6)0.0038 (5)0.0012 (6)
N40.0408 (7)0.0447 (8)0.0469 (7)0.0008 (6)0.0070 (5)0.0016 (6)
O10.0450 (6)0.0579 (7)0.0769 (8)−0.0079 (5)0.0111 (5)−0.0047 (6)
O20.0624 (8)0.0551 (7)0.0686 (7)−0.0029 (6)0.0017 (6)−0.0150 (6)

Geometric parameters (Å, °)

C1—N31.3041 (19)C13—H13A0.9700
C1—O21.3558 (19)C13—H13B0.9700
C1—C21.405 (2)C14—C151.379 (2)
C2—C31.343 (2)C14—C171.386 (2)
C2—H20.9300C15—C161.374 (2)
C3—C41.413 (2)C15—H150.9300
C3—H30.9300C16—N11.322 (2)
C4—C51.403 (2)C16—H160.9300
C4—C61.418 (2)C17—C181.369 (3)
C5—N31.3641 (19)C17—H170.9300
C5—C81.433 (2)C18—N11.335 (3)
C6—C71.339 (2)C18—H180.9300
C6—H60.9300C19—C211.370 (2)
C7—C91.421 (2)C19—C231.377 (2)
C7—H70.9300C19—C241.492 (2)
C8—N41.3681 (18)C20—N21.330 (3)
C8—C91.401 (2)C20—C211.372 (3)
C9—C101.410 (2)C20—H200.9300
C10—C111.349 (2)C21—H210.9300
C10—H100.9300C22—N21.325 (3)
C11—C121.402 (2)C22—C231.372 (3)
C11—H110.9300C22—H220.9300
C12—N41.2992 (18)C23—H230.9300
C12—O11.3636 (17)C24—O21.436 (2)
C13—O11.432 (2)C24—H24A0.9700
C13—C141.490 (2)C24—H24B0.9700
N3—C1—O2119.50 (14)C15—C14—C17116.50 (16)
N3—C1—C2124.64 (16)C15—C14—C13122.91 (15)
O2—C1—C2115.86 (15)C17—C14—C13120.58 (16)
C3—C2—C1117.91 (16)C16—C15—C14119.77 (17)
C3—C2—H2121.0C16—C15—H15120.1
C1—C2—H2121.0C14—C15—H15120.1
C2—C3—C4120.48 (15)N1—C16—C15124.57 (19)
C2—C3—H3119.8N1—C16—H16117.7
C4—C3—H3119.8C15—C16—H16117.7
C5—C4—C3117.10 (15)C18—C17—C14119.14 (17)
C5—C4—C6119.59 (15)C18—C17—H17120.4
C3—C4—C6123.31 (15)C14—C17—H17120.4
N3—C5—C4122.25 (14)N1—C18—C17124.95 (18)
N3—C5—C8118.29 (12)N1—C18—H18117.5
C4—C5—C8119.46 (14)C17—C18—H18117.5
C7—C6—C4120.99 (15)C21—C19—C23117.07 (17)
C7—C6—H6119.5C21—C19—C24122.29 (16)
C4—C6—H6119.5C23—C19—C24120.63 (15)
C6—C7—C9121.18 (16)N2—C20—C21124.7 (2)
C6—C7—H7119.4N2—C20—H20117.6
C9—C7—H7119.4C21—C20—H20117.6
N4—C8—C9122.16 (14)C19—C21—C20119.0 (2)
N4—C8—C5118.70 (13)C19—C21—H21120.5
C9—C8—C5119.14 (13)C20—C21—H21120.5
C8—C9—C10117.42 (14)N2—C22—C23123.7 (2)
C8—C9—C7119.64 (15)N2—C22—H22118.2
C10—C9—C7122.93 (15)C23—C22—H22118.2
C11—C10—C9120.31 (15)C22—C23—C19119.93 (18)
C11—C10—H10119.8C22—C23—H23120.0
C9—C10—H10119.8C19—C23—H23120.0
C10—C11—C12117.52 (15)O2—C24—C19111.04 (13)
C10—C11—H11121.2O2—C24—H24A109.4
C12—C11—H11121.2C19—C24—H24A109.4
N4—C12—O1119.88 (14)O2—C24—H24B109.4
N4—C12—C11125.30 (14)C19—C24—H24B109.4
O1—C12—C11114.82 (14)H24A—C24—H24B108.0
O1—C13—C14112.62 (14)C16—N1—C18115.06 (17)
O1—C13—H13A109.1C22—N2—C20115.61 (18)
C14—C13—H13A109.1C1—N3—C5117.62 (13)
O1—C13—H13B109.1C12—N4—C8117.24 (13)
C14—C13—H13B109.1C12—O1—C13118.41 (12)
H13A—C13—H13B107.8C1—O2—C24117.13 (12)
N3—C1—C2—C30.2 (2)C14—C15—C16—N10.5 (3)
O2—C1—C2—C3179.44 (14)C15—C14—C17—C180.8 (2)
C1—C2—C3—C4−0.3 (2)C13—C14—C17—C18−178.10 (16)
C2—C3—C4—C5−0.1 (2)C14—C17—C18—N10.2 (3)
C2—C3—C4—C6179.82 (15)C23—C19—C21—C200.4 (2)
C3—C4—C5—N30.7 (2)C24—C19—C21—C20−179.17 (16)
C6—C4—C5—N3−179.19 (13)N2—C20—C21—C19−1.4 (3)
C3—C4—C5—C8−179.77 (13)N2—C22—C23—C19−1.0 (3)
C6—C4—C5—C80.3 (2)C21—C19—C23—C220.7 (2)
C5—C4—C6—C7−0.1 (2)C24—C19—C23—C22−179.74 (15)
C3—C4—C6—C7179.96 (15)C21—C19—C24—O2106.35 (17)
C4—C6—C7—C9−0.1 (3)C23—C19—C24—O2−73.16 (19)
N3—C5—C8—N4−1.30 (19)C15—C16—N1—C180.5 (3)
C4—C5—C8—N4179.19 (12)C17—C18—N1—C16−0.8 (3)
N3—C5—C8—C9179.21 (12)C23—C22—N2—C200.1 (3)
C4—C5—C8—C9−0.3 (2)C21—C20—N2—C221.1 (3)
N4—C8—C9—C100.2 (2)O2—C1—N3—C5−178.81 (12)
C5—C8—C9—C10179.67 (13)C2—C1—N3—C50.4 (2)
N4—C8—C9—C7−179.36 (13)C4—C5—N3—C1−0.9 (2)
C5—C8—C9—C70.1 (2)C8—C5—N3—C1179.62 (12)
C6—C7—C9—C80.1 (2)O1—C12—N4—C8176.56 (12)
C6—C7—C9—C10−179.45 (16)C11—C12—N4—C8−2.9 (2)
C8—C9—C10—C11−1.1 (2)C9—C8—N4—C121.7 (2)
C7—C9—C10—C11178.44 (15)C5—C8—N4—C12−177.73 (12)
C9—C10—C11—C120.1 (2)N4—C12—O1—C13−0.8 (2)
C10—C11—C12—N42.1 (2)C11—C12—O1—C13178.80 (13)
C10—C11—C12—O1−177.47 (13)C14—C13—O1—C1297.39 (15)
O1—C13—C14—C15−8.9 (2)N3—C1—O2—C24−1.5 (2)
O1—C13—C14—C17169.93 (14)C2—C1—O2—C24179.22 (13)
C17—C14—C15—C16−1.1 (2)C19—C24—O2—C1−88.63 (16)
C13—C14—C15—C16177.76 (15)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2907).

References

  • Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Liu, Q. S., Liu, L. D. & Shi, J. M. (2008). Acta Cryst. C64, m58–m60. [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Zhang, S. G. & Hou, C. (2008). Acta Cryst. E64, o1450. [PMC free article] [PubMed]

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