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Acta Cryst. (2007). E63, o4052
https://doi.org/10.1107/S1600536807044224
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6-Meth­oxy-2-[tri(2-pyrid­yl)methyl­imino­meth­yl]phenol

Z.-H. Ni, L.-F. Zhang and H.-L. Wang
The title compound, C24H20N4O2 , is an unsymmetrical Schiff base which has potential as a hexa­dentate ligand. There is a relatively strong O—H...N intra­molecular hydrogen bond. The X-ray crystallographic results show that, despite the presence of the N4O2 group, the title compound does not exhibit a conformation conducive to hexa­dentate binding. The three pyridine rings show a propeller-like arrangement.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807044224/fl2160sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807044224/fl2160Isup2.hkl
Contains datablock I

CCDC reference: 663763

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.040
  • wR factor = 0.113
  • Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found




Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    C16    -   C17     ..       7.28 su


Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N3     -   C15     ..       5.71 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C12    -   C13     ..       5.07 su


Alert level G
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K


   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check
Comment top

Recently, Schiff base ligands have been widely used to assemble alkoxo- or phenoxo-bridged clusters and polymers with novel topological structures and interesting magnetic, catalytic and photochemical properties. (Koizumi et al., 2005; Chen et al., 2006; Karacan & Somer, 2004).

To date, many symmetrical and unsymmetrical Schiff bases with various coordination dentates have been synthesized (Arnold et al., 2003). Herein, we report a new unsymmetrical Schiff basel (I), which possesses an O2N4 donor set affording a potentially hexadentate ligand.

The geometry and labeling scheme for (I) are shown in Figure 1. The imide bond length of 1.2706 (17) Å for N1—C9 is slightly shorter than that of found in 6-Methoxy-2-[2-pyridylmethyliminomethyl]phenol (1.278 (3) Å) (Ni & Wang, 2007) and very similar to that of 4-Bromo-2-(2-pyridylmethyliminomethyl)phenol (1.269 (4) Å) (Zhang et al.,2003). There is a relatively strong intramolecular N···H—O bond in (I) with N···O1 at 2.581 (2) Å and N1···H1—O1 at 150.41 (12)° which is similar to what was found in related structures (Ni & Wang, 2007; Zhang et al., 2003).

It is noteworthy that the conformation of the three pyridine rings in (I) are significantly different from those in metal-organic complexes [Cu(NO2)2(tpmbz)] and [{Cu(NO2)(tpmsal)}2]·Et2O in which three pyridine rings chelate the Cu(II) ions as tripodal ligands (Arnold et al., 2003) indicating that (I) is not a good hexadentate candidate in its present conformation.

Related literature top

For related literature, see: Arnold et al. (1998, 2003); Chen et al. (2006); Karacan & Somer (2004); Koizumi et al. (2005); Ni & Wang (2007); Zhang et al. (2003).

Experimental top

The material 1,1,1-tris(2-pyridyl)methylamine (tpm) was prepared according to the literature (Arnold et al., 1998). The title compound was prepared as follows: tpm (0.02 mol) was added to a stirred ethanol solution of O-vanillin (0.02 mol, 30 ml). The reaction mixture was stirred about 1 h and then the mixture was allowed to stand at room temperature for about two days after which yellow block single cystals were collected. Yield: 60%. Elemental analysis [found (calculated)] for C24H20N4O2: C 72.82 (72.71), H 4.82 (5.06), N 14.10% (14.13%).

Refinement top

H atoms bound to C and O atoms were visible in difference maps and were placed using the HFIX commands in SHELXL-97 and refined with a riding model (C—H 0.97 Å or C—H 0.93 Å, and O—H 0.85 Å) with the constraint Uiso(H) = 1.5Ueq(methyl carrier), 1.5Ueq(O) and Uiso(H) = 1.2Ueq(C) for all other H atoms.

Structure description top

Recently, Schiff base ligands have been widely used to assemble alkoxo- or phenoxo-bridged clusters and polymers with novel topological structures and interesting magnetic, catalytic and photochemical properties. (Koizumi et al., 2005; Chen et al., 2006; Karacan & Somer, 2004).

To date, many symmetrical and unsymmetrical Schiff bases with various coordination dentates have been synthesized (Arnold et al., 2003). Herein, we report a new unsymmetrical Schiff basel (I), which possesses an O2N4 donor set affording a potentially hexadentate ligand.

The geometry and labeling scheme for (I) are shown in Figure 1. The imide bond length of 1.2706 (17) Å for N1—C9 is slightly shorter than that of found in 6-Methoxy-2-[2-pyridylmethyliminomethyl]phenol (1.278 (3) Å) (Ni & Wang, 2007) and very similar to that of 4-Bromo-2-(2-pyridylmethyliminomethyl)phenol (1.269 (4) Å) (Zhang et al.,2003). There is a relatively strong intramolecular N···H—O bond in (I) with N···O1 at 2.581 (2) Å and N1···H1—O1 at 150.41 (12)° which is similar to what was found in related structures (Ni & Wang, 2007; Zhang et al., 2003).

It is noteworthy that the conformation of the three pyridine rings in (I) are significantly different from those in metal-organic complexes [Cu(NO2)2(tpmbz)] and [{Cu(NO2)(tpmsal)}2]·Et2O in which three pyridine rings chelate the Cu(II) ions as tripodal ligands (Arnold et al., 2003) indicating that (I) is not a good hexadentate candidate in its present conformation.

For related literature, see: Arnold et al. (1998, 2003); Chen et al. (2006); Karacan & Somer (2004); Koizumi et al. (2005); Ni & Wang (2007); Zhang et al. (2003).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Sheldrick, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and XP (Sheldrick, 1998).

Figures top
[Figure 1] Fig. 1. A view of (I) with the unique atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
6-Methoxy-2-[tri(2-pyridyl)methyliminomethyl]phenol top
Crystal data top
C24H20N4O2Z = 2
Mr = 396.44F(000) = 416
Triclinic, P1Dx = 1.291 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.8601 (17) ÅCell parameters from 3737 reflections
b = 10.706 (2) Åθ = 1.9–25.5°
c = 11.147 (2) ŵ = 0.09 mm−1
α = 80.240 (8)°T = 273 K
β = 78.177 (8)°Block, yellow
γ = 87.504 (9)°0.20 × 0.16 × 0.10 mm
V = 1019.9 (3) Å3
Data collection top
Bruker APEXII CCD area-detector
diffractometer		3737 independent reflections
Radiation source: fine-focus sealed tube3299 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
φ and ω scansθmax = 25.5°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		h = −10→9
Tmin = 0.982, Tmax = 0.994k = −12→9
8063 measured reflectionsl = −13→13
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-atom parameters not refined
wR(F2) = 0.113 w = 1/[σ2(Fo2) + (0.0738P)2 + 0.2154P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
3737 reflectionsΔρmax = 0.20 e Å−3
271 parametersΔρmin = −0.21 e Å−3
Primary atom site location: structure-invariant direct methods
Crystal data top
C24H20N4O2γ = 87.504 (9)°
Mr = 396.44V = 1019.9 (3) Å3
Triclinic, P1Z = 2
a = 8.8601 (17) ÅMo Kα radiation
b = 10.706 (2) ŵ = 0.09 mm−1
c = 11.147 (2) ÅT = 273 K
α = 80.240 (8)°0.20 × 0.16 × 0.10 mm
β = 78.177 (8)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer		3737 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)		3299 reflections with I > 2σ(I)
Tmin = 0.982, Tmax = 0.994Rint = 0.018
8063 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.040271 parameters
wR(F2) = 0.113H-atom parameters not refined
S = 1.01Δρmax = 0.20 e Å−3
3737 reflectionsΔρmin = −0.21 e Å−3
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
xyzUiso*/Ueq
N10.33266 (12)0.74242 (10)1.02986 (9)0.0385 (2)
C60.32798 (15)0.75382 (12)1.24160 (11)0.0411 (3)
C70.40038 (15)0.77263 (13)1.11077 (12)0.0420 (3)
H7A0.49840.80751.08560.050*
C160.66470 (16)0.68999 (16)0.91031 (14)0.0561 (4)
H16A0.62180.61330.95280.067*
C130.2638 (2)0.46101 (15)0.74375 (17)0.0654 (4)
H13A0.22940.39470.71240.078*
C170.82107 (19)0.7082 (2)0.88838 (17)0.0725 (5)
H17A0.88470.64360.91720.087*
O10.09906 (11)0.66779 (10)1.20396 (8)0.0502 (3)
O2−0.03696 (12)0.64400 (11)1.43905 (9)0.0589 (3)
C10.17907 (15)0.70342 (12)1.28201 (11)0.0395 (3)
C90.39813 (13)0.76771 (11)0.89521 (10)0.0351 (3)
C150.57358 (14)0.78706 (12)0.86825 (11)0.0386 (3)
C200.31630 (13)0.88584 (11)0.83720 (11)0.0362 (3)
C100.35609 (14)0.65406 (12)0.84055 (11)0.0381 (3)
N40.32578 (15)0.89811 (11)0.71510 (10)0.0499 (3)
C20.10966 (16)0.69167 (13)1.40953 (12)0.0464 (3)
N30.63130 (14)0.89841 (12)0.80865 (13)0.0563 (3)
C30.1897 (2)0.72685 (15)1.49179 (13)0.0580 (4)
H3B0.14400.71831.57560.070*
N20.21454 (13)0.60759 (12)0.88633 (12)0.0518 (3)
C50.40627 (18)0.78922 (15)1.32790 (13)0.0546 (4)
H5A0.50500.82241.30120.066*
C210.23894 (17)0.97280 (14)0.90640 (14)0.0511 (3)
H21A0.23380.96180.99170.061*
C40.3381 (2)0.77516 (16)1.45114 (14)0.0620 (4)
H4B0.39120.79791.50790.074*
C230.17926 (19)1.09068 (15)0.72196 (17)0.0609 (4)
H23A0.13361.15980.67990.073*
C240.2584 (2)1.00038 (15)0.65985 (15)0.0610 (4)
H24A0.26581.01050.57430.073*
C180.88412 (17)0.8203 (2)0.82472 (17)0.0666 (5)
H18A0.99010.83270.80800.080*
C140.1720 (2)0.51215 (16)0.83700 (17)0.0611 (4)
H14A0.07390.47890.86840.073*
C190.78688 (18)0.91319 (17)0.78668 (18)0.0666 (5)
H19A0.82830.99020.74370.080*
C220.16936 (18)1.07631 (15)0.84721 (17)0.0615 (4)
H22A0.11621.13570.89230.074*
C110.4556 (2)0.60833 (15)0.74578 (14)0.0599 (4)
H11A0.55300.64300.71480.072*
C120.4077 (2)0.50963 (17)0.69741 (17)0.0738 (5)
H12A0.47320.47660.63370.089*
C8−0.1187 (2)0.6382 (2)1.56427 (16)0.0797 (6)
H8A−0.21920.60351.57270.120*
H8B−0.12900.72191.58520.120*
H8C−0.06300.58511.61910.120*
H10.15790.68041.13180.120*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0365 (5)0.0469 (6)0.0328 (5)−0.0028 (4)−0.0057 (4)−0.0091 (4)
C60.0468 (7)0.0432 (7)0.0350 (6)−0.0018 (5)−0.0100 (5)−0.0084 (5)
C70.0380 (6)0.0491 (7)0.0397 (7)−0.0070 (5)−0.0067 (5)−0.0094 (5)
C160.0411 (7)0.0637 (9)0.0540 (8)0.0056 (6)−0.0037 (6)0.0082 (7)
C130.0937 (13)0.0435 (8)0.0690 (10)−0.0053 (8)−0.0311 (9)−0.0178 (7)
C170.0472 (9)0.0974 (14)0.0686 (11)0.0196 (9)−0.0127 (8)−0.0050 (10)
O10.0444 (5)0.0670 (6)0.0399 (5)−0.0136 (4)−0.0046 (4)−0.0122 (4)
O20.0577 (6)0.0671 (7)0.0428 (5)−0.0029 (5)0.0074 (5)−0.0042 (5)
C10.0463 (7)0.0374 (6)0.0347 (6)0.0014 (5)−0.0072 (5)−0.0069 (5)
C90.0334 (6)0.0403 (6)0.0319 (6)−0.0014 (5)−0.0049 (5)−0.0081 (5)
C150.0350 (6)0.0478 (7)0.0341 (6)−0.0002 (5)−0.0051 (5)−0.0118 (5)
C200.0317 (6)0.0393 (6)0.0402 (6)−0.0033 (5)−0.0092 (5)−0.0103 (5)
C100.0424 (7)0.0363 (6)0.0364 (6)0.0011 (5)−0.0099 (5)−0.0063 (5)
N40.0634 (7)0.0481 (7)0.0426 (6)0.0057 (5)−0.0198 (5)−0.0101 (5)
C20.0548 (8)0.0417 (7)0.0376 (7)0.0041 (6)−0.0016 (6)−0.0029 (5)
N30.0457 (7)0.0509 (7)0.0732 (8)−0.0057 (5)−0.0081 (6)−0.0157 (6)
C30.0813 (11)0.0601 (9)0.0307 (6)0.0065 (8)−0.0076 (7)−0.0090 (6)
N20.0439 (6)0.0542 (7)0.0615 (7)−0.0059 (5)−0.0114 (5)−0.0190 (6)
C50.0587 (9)0.0645 (9)0.0462 (8)−0.0082 (7)−0.0171 (7)−0.0147 (7)
C210.0518 (8)0.0523 (8)0.0509 (8)0.0074 (6)−0.0089 (6)−0.0167 (6)
C40.0817 (11)0.0700 (10)0.0422 (8)−0.0031 (8)−0.0231 (8)−0.0178 (7)
C230.0581 (9)0.0444 (8)0.0852 (12)0.0050 (7)−0.0321 (8)−0.0044 (7)
C240.0783 (11)0.0555 (9)0.0547 (9)0.0027 (8)−0.0313 (8)−0.0033 (7)
C180.0343 (7)0.0971 (14)0.0726 (11)−0.0035 (8)−0.0057 (7)−0.0309 (10)
C140.0593 (9)0.0547 (9)0.0768 (11)−0.0104 (7)−0.0225 (8)−0.0182 (8)
C190.0480 (9)0.0624 (10)0.0895 (12)−0.0136 (7)−0.0047 (8)−0.0210 (9)
C220.0567 (9)0.0490 (9)0.0816 (11)0.0130 (7)−0.0150 (8)−0.0201 (8)
C110.0651 (10)0.0586 (9)0.0536 (8)−0.0081 (7)0.0071 (7)−0.0237 (7)
C120.1006 (14)0.0615 (10)0.0604 (10)0.0029 (10)−0.0011 (9)−0.0324 (8)
C80.0846 (13)0.0830 (13)0.0548 (10)−0.0039 (10)0.0249 (9)−0.0112 (9)
Geometric parameters (Å, º) top
N1—C71.2711 (16)N4—C241.3416 (19)
N1—C91.4771 (15)C2—C31.376 (2)
C6—C51.4037 (18)N3—C191.361 (2)
C6—C11.4038 (19)C3—C41.392 (2)
C6—C71.4516 (18)C3—H3B0.9300
C7—H7A0.9300N2—C141.3408 (19)
C16—C151.3669 (19)C5—C41.368 (2)
C16—C171.373 (2)C5—H5A0.9300
C16—H16A0.9300C21—C221.379 (2)
C13—C141.360 (2)C21—H21A0.9300
C13—C121.364 (3)C4—H4B0.9300
C13—H13A0.9300C23—C221.363 (2)
C17—C181.365 (3)C23—C241.369 (2)
C17—H17A0.9300C23—H23A0.9300
O1—C11.3393 (15)C24—H24A0.9300
O1—H10.8570C18—C191.357 (3)
O2—C21.3718 (18)C18—H18A0.9300
O2—C81.4272 (18)C14—H14A0.9300
C1—C21.4152 (18)C19—H19A0.9300
C9—C151.5379 (16)C22—H22A0.9300
C9—C201.5421 (17)C11—C121.383 (2)
C9—C101.5408 (17)C11—H11A0.9300
C15—N31.3302 (19)C12—H12A0.9300
C20—N41.3306 (16)C8—H8A0.9600
C20—C211.3795 (18)C8—H8B0.9600
C10—N21.3367 (17)C8—H8C0.9600
C10—C111.3744 (19)
C7—N1—C9122.94 (11)C2—C3—H3B119.6
C5—C6—C1119.81 (12)C4—C3—H3B119.6
C5—C6—C7119.61 (13)C10—N2—C14117.38 (13)
C1—C6—C7120.57 (11)C4—C5—C6120.38 (15)
N1—C7—C6121.38 (12)C4—C5—H5A119.8
N1—C7—H7A119.3C6—C5—H5A119.8
C6—C7—H7A119.3C20—C21—C22119.03 (14)
C15—C16—C17118.52 (15)C20—C21—H21A120.5
C15—C16—H16A120.7C22—C21—H21A120.5
C17—C16—H16A120.7C5—C4—C3120.20 (14)
C14—C13—C12118.17 (14)C5—C4—H4B119.9
C14—C13—H13A120.9C3—C4—H4B119.9
C12—C13—H13A120.9C22—C23—C24118.06 (14)
C18—C17—C16120.67 (16)C22—C23—H23A121.0
C18—C17—H17A119.7C24—C23—H23A121.0
C16—C17—H17A119.7N4—C24—C23123.86 (15)
C1—O1—H1106.3N4—C24—H24A118.1
C2—O2—C8117.61 (13)C23—C24—H24A118.1
O1—C1—C6122.42 (11)C19—C18—C17117.75 (15)
O1—C1—C2118.66 (12)C19—C18—H18A121.1
C6—C1—C2118.92 (12)C17—C18—H18A121.1
N1—C9—C15112.03 (9)N2—C14—C13123.90 (16)
N1—C9—C20108.17 (9)N2—C14—H14A118.0
C15—C9—C20110.75 (10)C13—C14—H14A118.0
N1—C9—C10106.79 (10)C18—C19—N3122.84 (16)
C15—C9—C10111.39 (10)C18—C19—H19A118.6
C20—C9—C10107.49 (9)N3—C19—H19A118.6
N3—C15—C16122.15 (13)C23—C22—C21119.38 (14)
N3—C15—C9119.26 (11)C23—C22—H22A120.3
C16—C15—C9118.55 (12)C21—C22—H22A120.3
N4—C20—C21122.23 (12)C10—C11—C12118.59 (15)
N4—C20—C9115.11 (10)C10—C11—H11A120.7
C21—C20—C9122.66 (11)C12—C11—H11A120.7
N2—C10—C11122.35 (12)C13—C12—C11119.60 (15)
N2—C10—C9115.91 (10)C13—C12—H12A120.2
C11—C10—C9121.65 (12)C11—C12—H12A120.2
C20—N4—C24117.43 (12)O2—C8—H8A109.5
O2—C2—C3125.78 (12)O2—C8—H8B109.5
O2—C2—C1114.39 (12)H8A—C8—H8B109.5
C3—C2—C1119.82 (14)O2—C8—H8C109.5
C15—N3—C19118.03 (14)H8A—C8—H8C109.5
C2—C3—C4120.86 (13)H8B—C8—H8C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.86??2.581 (2)150 (1)

Experimental details

Crystal data
Chemical formulaC24H20N4O2
Mr396.44
Crystal system, space groupTriclinic, P1
Temperature (K)273
a, b, c (Å)8.8601 (17), 10.706 (2), 11.147 (2)
α, β, γ (°)80.240 (8), 78.177 (8), 87.504 (9)
V (Å3)1019.9 (3)
Z2
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.20 × 0.16 × 0.10
Data collection
DiffractometerBruker APEXII CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.982, 0.994
No. of measured, independent and
observed [I > 2σ(I)] reflections		8063, 3737, 3299
Rint0.018
(sin θ/λ)max (Å−1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.113, 1.01
No. of reflections3737
No. of parameters271
No. of restraints?
H-atom treatmentH-atom parameters not refined
Δρmax, Δρmin (e Å−3)0.20, −0.21

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997) and XP (Sheldrick, 1998).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.86??2.581 (2)150.41 (12)
 

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