Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807044224/fl2160sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807044224/fl2160Isup2.hkl |
CCDC reference: 663763
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (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
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).
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%).
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.
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).
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).
Fig. 1. A view of (I) with the unique atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. |
C24H20N4O2 | Z = 2 |
Mr = 396.44 | F(000) = 416 |
Triclinic, P1 | Dx = 1.291 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.8601 (17) Å | Cell parameters from 3737 reflections |
b = 10.706 (2) Å | θ = 1.9–25.5° |
c = 11.147 (2) Å | µ = 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 |
Bruker APEXII CCD area-detector diffractometer | 3737 independent reflections |
Radiation source: fine-focus sealed tube | 3299 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
φ and ω scans | θmax = 25.5°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −10→9 |
Tmin = 0.982, Tmax = 0.994 | k = −12→9 |
8063 measured reflections | l = −13→13 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | H-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 reflections | Δρmax = 0.20 e Å−3 |
271 parameters | Δρmin = −0.21 e Å−3 |
Primary atom site location: structure-invariant direct methods |
C24H20N4O2 | γ = 87.504 (9)° |
Mr = 396.44 | V = 1019.9 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.8601 (17) Å | Mo Kα radiation |
b = 10.706 (2) Å | µ = 0.09 mm−1 |
c = 11.147 (2) Å | T = 273 K |
α = 80.240 (8)° | 0.20 × 0.16 × 0.10 mm |
β = 78.177 (8)° |
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 = 0.994 | Rint = 0.018 |
8063 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 271 parameters |
wR(F2) = 0.113 | H-atom parameters not refined |
S = 1.01 | Δρmax = 0.20 e Å−3 |
3737 reflections | Δρmin = −0.21 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.33266 (12) | 0.74242 (10) | 1.02986 (9) | 0.0385 (2) | |
C6 | 0.32798 (15) | 0.75382 (12) | 1.24160 (11) | 0.0411 (3) | |
C7 | 0.40038 (15) | 0.77263 (13) | 1.11077 (12) | 0.0420 (3) | |
H7A | 0.4984 | 0.8075 | 1.0856 | 0.050* | |
C16 | 0.66470 (16) | 0.68999 (16) | 0.91031 (14) | 0.0561 (4) | |
H16A | 0.6218 | 0.6133 | 0.9528 | 0.067* | |
C13 | 0.2638 (2) | 0.46101 (15) | 0.74375 (17) | 0.0654 (4) | |
H13A | 0.2294 | 0.3947 | 0.7124 | 0.078* | |
C17 | 0.82107 (19) | 0.7082 (2) | 0.88838 (17) | 0.0725 (5) | |
H17A | 0.8847 | 0.6436 | 0.9172 | 0.087* | |
O1 | 0.09906 (11) | 0.66779 (10) | 1.20396 (8) | 0.0502 (3) | |
O2 | −0.03696 (12) | 0.64400 (11) | 1.43905 (9) | 0.0589 (3) | |
C1 | 0.17907 (15) | 0.70342 (12) | 1.28201 (11) | 0.0395 (3) | |
C9 | 0.39813 (13) | 0.76771 (11) | 0.89521 (10) | 0.0351 (3) | |
C15 | 0.57358 (14) | 0.78706 (12) | 0.86825 (11) | 0.0386 (3) | |
C20 | 0.31630 (13) | 0.88584 (11) | 0.83720 (11) | 0.0362 (3) | |
C10 | 0.35609 (14) | 0.65406 (12) | 0.84055 (11) | 0.0381 (3) | |
N4 | 0.32578 (15) | 0.89811 (11) | 0.71510 (10) | 0.0499 (3) | |
C2 | 0.10966 (16) | 0.69167 (13) | 1.40953 (12) | 0.0464 (3) | |
N3 | 0.63130 (14) | 0.89841 (12) | 0.80865 (13) | 0.0563 (3) | |
C3 | 0.1897 (2) | 0.72685 (15) | 1.49179 (13) | 0.0580 (4) | |
H3B | 0.1440 | 0.7183 | 1.5756 | 0.070* | |
N2 | 0.21454 (13) | 0.60759 (12) | 0.88633 (12) | 0.0518 (3) | |
C5 | 0.40627 (18) | 0.78922 (15) | 1.32790 (13) | 0.0546 (4) | |
H5A | 0.5050 | 0.8224 | 1.3012 | 0.066* | |
C21 | 0.23894 (17) | 0.97280 (14) | 0.90640 (14) | 0.0511 (3) | |
H21A | 0.2338 | 0.9618 | 0.9917 | 0.061* | |
C4 | 0.3381 (2) | 0.77516 (16) | 1.45114 (14) | 0.0620 (4) | |
H4B | 0.3912 | 0.7979 | 1.5079 | 0.074* | |
C23 | 0.17926 (19) | 1.09068 (15) | 0.72196 (17) | 0.0609 (4) | |
H23A | 0.1336 | 1.1598 | 0.6799 | 0.073* | |
C24 | 0.2584 (2) | 1.00038 (15) | 0.65985 (15) | 0.0610 (4) | |
H24A | 0.2658 | 1.0105 | 0.5743 | 0.073* | |
C18 | 0.88412 (17) | 0.8203 (2) | 0.82472 (17) | 0.0666 (5) | |
H18A | 0.9901 | 0.8327 | 0.8080 | 0.080* | |
C14 | 0.1720 (2) | 0.51215 (16) | 0.83700 (17) | 0.0611 (4) | |
H14A | 0.0739 | 0.4789 | 0.8684 | 0.073* | |
C19 | 0.78688 (18) | 0.91319 (17) | 0.78668 (18) | 0.0666 (5) | |
H19A | 0.8283 | 0.9902 | 0.7437 | 0.080* | |
C22 | 0.16936 (18) | 1.07631 (15) | 0.84721 (17) | 0.0615 (4) | |
H22A | 0.1162 | 1.1357 | 0.8923 | 0.074* | |
C11 | 0.4556 (2) | 0.60833 (15) | 0.74578 (14) | 0.0599 (4) | |
H11A | 0.5530 | 0.6430 | 0.7148 | 0.072* | |
C12 | 0.4077 (2) | 0.50963 (17) | 0.69741 (17) | 0.0738 (5) | |
H12A | 0.4732 | 0.4766 | 0.6337 | 0.089* | |
C8 | −0.1187 (2) | 0.6382 (2) | 1.56427 (16) | 0.0797 (6) | |
H8A | −0.2192 | 0.6035 | 1.5727 | 0.120* | |
H8B | −0.1290 | 0.7219 | 1.5852 | 0.120* | |
H8C | −0.0630 | 0.5851 | 1.6191 | 0.120* | |
H1 | 0.1579 | 0.6804 | 1.1318 | 0.120* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0365 (5) | 0.0469 (6) | 0.0328 (5) | −0.0028 (4) | −0.0057 (4) | −0.0091 (4) |
C6 | 0.0468 (7) | 0.0432 (7) | 0.0350 (6) | −0.0018 (5) | −0.0100 (5) | −0.0084 (5) |
C7 | 0.0380 (6) | 0.0491 (7) | 0.0397 (7) | −0.0070 (5) | −0.0067 (5) | −0.0094 (5) |
C16 | 0.0411 (7) | 0.0637 (9) | 0.0540 (8) | 0.0056 (6) | −0.0037 (6) | 0.0082 (7) |
C13 | 0.0937 (13) | 0.0435 (8) | 0.0690 (10) | −0.0053 (8) | −0.0311 (9) | −0.0178 (7) |
C17 | 0.0472 (9) | 0.0974 (14) | 0.0686 (11) | 0.0196 (9) | −0.0127 (8) | −0.0050 (10) |
O1 | 0.0444 (5) | 0.0670 (6) | 0.0399 (5) | −0.0136 (4) | −0.0046 (4) | −0.0122 (4) |
O2 | 0.0577 (6) | 0.0671 (7) | 0.0428 (5) | −0.0029 (5) | 0.0074 (5) | −0.0042 (5) |
C1 | 0.0463 (7) | 0.0374 (6) | 0.0347 (6) | 0.0014 (5) | −0.0072 (5) | −0.0069 (5) |
C9 | 0.0334 (6) | 0.0403 (6) | 0.0319 (6) | −0.0014 (5) | −0.0049 (5) | −0.0081 (5) |
C15 | 0.0350 (6) | 0.0478 (7) | 0.0341 (6) | −0.0002 (5) | −0.0051 (5) | −0.0118 (5) |
C20 | 0.0317 (6) | 0.0393 (6) | 0.0402 (6) | −0.0033 (5) | −0.0092 (5) | −0.0103 (5) |
C10 | 0.0424 (7) | 0.0363 (6) | 0.0364 (6) | 0.0011 (5) | −0.0099 (5) | −0.0063 (5) |
N4 | 0.0634 (7) | 0.0481 (7) | 0.0426 (6) | 0.0057 (5) | −0.0198 (5) | −0.0101 (5) |
C2 | 0.0548 (8) | 0.0417 (7) | 0.0376 (7) | 0.0041 (6) | −0.0016 (6) | −0.0029 (5) |
N3 | 0.0457 (7) | 0.0509 (7) | 0.0732 (8) | −0.0057 (5) | −0.0081 (6) | −0.0157 (6) |
C3 | 0.0813 (11) | 0.0601 (9) | 0.0307 (6) | 0.0065 (8) | −0.0076 (7) | −0.0090 (6) |
N2 | 0.0439 (6) | 0.0542 (7) | 0.0615 (7) | −0.0059 (5) | −0.0114 (5) | −0.0190 (6) |
C5 | 0.0587 (9) | 0.0645 (9) | 0.0462 (8) | −0.0082 (7) | −0.0171 (7) | −0.0147 (7) |
C21 | 0.0518 (8) | 0.0523 (8) | 0.0509 (8) | 0.0074 (6) | −0.0089 (6) | −0.0167 (6) |
C4 | 0.0817 (11) | 0.0700 (10) | 0.0422 (8) | −0.0031 (8) | −0.0231 (8) | −0.0178 (7) |
C23 | 0.0581 (9) | 0.0444 (8) | 0.0852 (12) | 0.0050 (7) | −0.0321 (8) | −0.0044 (7) |
C24 | 0.0783 (11) | 0.0555 (9) | 0.0547 (9) | 0.0027 (8) | −0.0313 (8) | −0.0033 (7) |
C18 | 0.0343 (7) | 0.0971 (14) | 0.0726 (11) | −0.0035 (8) | −0.0057 (7) | −0.0309 (10) |
C14 | 0.0593 (9) | 0.0547 (9) | 0.0768 (11) | −0.0104 (7) | −0.0225 (8) | −0.0182 (8) |
C19 | 0.0480 (9) | 0.0624 (10) | 0.0895 (12) | −0.0136 (7) | −0.0047 (8) | −0.0210 (9) |
C22 | 0.0567 (9) | 0.0490 (9) | 0.0816 (11) | 0.0130 (7) | −0.0150 (8) | −0.0201 (8) |
C11 | 0.0651 (10) | 0.0586 (9) | 0.0536 (8) | −0.0081 (7) | 0.0071 (7) | −0.0237 (7) |
C12 | 0.1006 (14) | 0.0615 (10) | 0.0604 (10) | 0.0029 (10) | −0.0011 (9) | −0.0324 (8) |
C8 | 0.0846 (13) | 0.0830 (13) | 0.0548 (10) | −0.0039 (10) | 0.0249 (9) | −0.0112 (9) |
N1—C7 | 1.2711 (16) | N4—C24 | 1.3416 (19) |
N1—C9 | 1.4771 (15) | C2—C3 | 1.376 (2) |
C6—C5 | 1.4037 (18) | N3—C19 | 1.361 (2) |
C6—C1 | 1.4038 (19) | C3—C4 | 1.392 (2) |
C6—C7 | 1.4516 (18) | C3—H3B | 0.9300 |
C7—H7A | 0.9300 | N2—C14 | 1.3408 (19) |
C16—C15 | 1.3669 (19) | C5—C4 | 1.368 (2) |
C16—C17 | 1.373 (2) | C5—H5A | 0.9300 |
C16—H16A | 0.9300 | C21—C22 | 1.379 (2) |
C13—C14 | 1.360 (2) | C21—H21A | 0.9300 |
C13—C12 | 1.364 (3) | C4—H4B | 0.9300 |
C13—H13A | 0.9300 | C23—C22 | 1.363 (2) |
C17—C18 | 1.365 (3) | C23—C24 | 1.369 (2) |
C17—H17A | 0.9300 | C23—H23A | 0.9300 |
O1—C1 | 1.3393 (15) | C24—H24A | 0.9300 |
O1—H1 | 0.8570 | C18—C19 | 1.357 (3) |
O2—C2 | 1.3718 (18) | C18—H18A | 0.9300 |
O2—C8 | 1.4272 (18) | C14—H14A | 0.9300 |
C1—C2 | 1.4152 (18) | C19—H19A | 0.9300 |
C9—C15 | 1.5379 (16) | C22—H22A | 0.9300 |
C9—C20 | 1.5421 (17) | C11—C12 | 1.383 (2) |
C9—C10 | 1.5408 (17) | C11—H11A | 0.9300 |
C15—N3 | 1.3302 (19) | C12—H12A | 0.9300 |
C20—N4 | 1.3306 (16) | C8—H8A | 0.9600 |
C20—C21 | 1.3795 (18) | C8—H8B | 0.9600 |
C10—N2 | 1.3367 (17) | C8—H8C | 0.9600 |
C10—C11 | 1.3744 (19) | ||
C7—N1—C9 | 122.94 (11) | C2—C3—H3B | 119.6 |
C5—C6—C1 | 119.81 (12) | C4—C3—H3B | 119.6 |
C5—C6—C7 | 119.61 (13) | C10—N2—C14 | 117.38 (13) |
C1—C6—C7 | 120.57 (11) | C4—C5—C6 | 120.38 (15) |
N1—C7—C6 | 121.38 (12) | C4—C5—H5A | 119.8 |
N1—C7—H7A | 119.3 | C6—C5—H5A | 119.8 |
C6—C7—H7A | 119.3 | C20—C21—C22 | 119.03 (14) |
C15—C16—C17 | 118.52 (15) | C20—C21—H21A | 120.5 |
C15—C16—H16A | 120.7 | C22—C21—H21A | 120.5 |
C17—C16—H16A | 120.7 | C5—C4—C3 | 120.20 (14) |
C14—C13—C12 | 118.17 (14) | C5—C4—H4B | 119.9 |
C14—C13—H13A | 120.9 | C3—C4—H4B | 119.9 |
C12—C13—H13A | 120.9 | C22—C23—C24 | 118.06 (14) |
C18—C17—C16 | 120.67 (16) | C22—C23—H23A | 121.0 |
C18—C17—H17A | 119.7 | C24—C23—H23A | 121.0 |
C16—C17—H17A | 119.7 | N4—C24—C23 | 123.86 (15) |
C1—O1—H1 | 106.3 | N4—C24—H24A | 118.1 |
C2—O2—C8 | 117.61 (13) | C23—C24—H24A | 118.1 |
O1—C1—C6 | 122.42 (11) | C19—C18—C17 | 117.75 (15) |
O1—C1—C2 | 118.66 (12) | C19—C18—H18A | 121.1 |
C6—C1—C2 | 118.92 (12) | C17—C18—H18A | 121.1 |
N1—C9—C15 | 112.03 (9) | N2—C14—C13 | 123.90 (16) |
N1—C9—C20 | 108.17 (9) | N2—C14—H14A | 118.0 |
C15—C9—C20 | 110.75 (10) | C13—C14—H14A | 118.0 |
N1—C9—C10 | 106.79 (10) | C18—C19—N3 | 122.84 (16) |
C15—C9—C10 | 111.39 (10) | C18—C19—H19A | 118.6 |
C20—C9—C10 | 107.49 (9) | N3—C19—H19A | 118.6 |
N3—C15—C16 | 122.15 (13) | C23—C22—C21 | 119.38 (14) |
N3—C15—C9 | 119.26 (11) | C23—C22—H22A | 120.3 |
C16—C15—C9 | 118.55 (12) | C21—C22—H22A | 120.3 |
N4—C20—C21 | 122.23 (12) | C10—C11—C12 | 118.59 (15) |
N4—C20—C9 | 115.11 (10) | C10—C11—H11A | 120.7 |
C21—C20—C9 | 122.66 (11) | C12—C11—H11A | 120.7 |
N2—C10—C11 | 122.35 (12) | C13—C12—C11 | 119.60 (15) |
N2—C10—C9 | 115.91 (10) | C13—C12—H12A | 120.2 |
C11—C10—C9 | 121.65 (12) | C11—C12—H12A | 120.2 |
C20—N4—C24 | 117.43 (12) | O2—C8—H8A | 109.5 |
O2—C2—C3 | 125.78 (12) | O2—C8—H8B | 109.5 |
O2—C2—C1 | 114.39 (12) | H8A—C8—H8B | 109.5 |
C3—C2—C1 | 119.82 (14) | O2—C8—H8C | 109.5 |
C15—N3—C19 | 118.03 (14) | H8A—C8—H8C | 109.5 |
C2—C3—C4 | 120.86 (13) | H8B—C8—H8C | 109.5 |
Experimental details
Crystal data | |
Chemical formula | C24H20N4O2 |
Mr | 396.44 |
Crystal system, space group | Triclinic, 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) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.20 × 0.16 × 0.10 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2003) |
Tmin, Tmax | 0.982, 0.994 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8063, 3737, 3299 |
Rint | 0.018 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.113, 1.01 |
No. of reflections | 3737 |
No. of parameters | 271 |
No. of restraints | ? |
H-atom treatment | H-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).
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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.