Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010403272X/hj1037sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S010827010403272X/hj1037Isup2.hkl |
CCDC reference: 264798
The title compound was prepared from 4,4'-methylenedianiline and 3-pyridinecarboxaldehyde. Single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation from an ethanol solution at room temperature.
All H atoms were initially located in a difference Fourier map and were refined freely along with an isotropic displacement parameter.
Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97; software used to prepare material for publication: Please provide missing information.
C25H20N4 | F(000) = 396 |
Mr = 376.45 | Dx = 1.275 Mg m−3 |
Monoclinic, Pc | Mo Kα radiation, λ = 0.71073 Å |
a = 18.7505 (10) Å | Cell parameters from 25 reflections |
b = 4.6414 (10) Å | θ = 8–17.6° |
c = 11.3866 (10) Å | µ = 0.08 mm−1 |
β = 98.394 (10)° | T = 293 K |
V = 980.3 (2) Å3 | Block, yellow |
Z = 2 | 0.4 × 0.35 × 0.26 mm |
Enraf Nonius CAD-4 diffractometer | Rint = 0.035 |
ω scans | θmax = 26°, θmin = 2.2° |
Absorption correction: ψ scan (North et al., 1968) | h = −23→22 |
Tmin = 0.956, Tmax = 0.980 | k = −5→5 |
3793 measured reflections | l = 0→14 |
1920 independent reflections | 2 standard reflections every 3600 reflections |
1287 reflections with I > 2σ(I) | intensity decay: <97 |
Refinement on F2 | All H-atom parameters refined |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.031P)2] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.035 | (Δ/σ)max = 0.001 |
wR(F2) = 0.071 | Δρmax = 0.11 e Å−3 |
S = 1.02 | Δρmin = −0.10 e Å−3 |
1920 reflections | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
343 parameters | Extinction coefficient: 0.028 (4) |
2 restraints |
C25H20N4 | V = 980.3 (2) Å3 |
Mr = 376.45 | Z = 2 |
Monoclinic, Pc | Mo Kα radiation |
a = 18.7505 (10) Å | µ = 0.08 mm−1 |
b = 4.6414 (10) Å | T = 293 K |
c = 11.3866 (10) Å | 0.4 × 0.35 × 0.26 mm |
β = 98.394 (10)° |
Enraf Nonius CAD-4 diffractometer | 1287 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.035 |
Tmin = 0.956, Tmax = 0.980 | 2 standard reflections every 3600 reflections |
3793 measured reflections | intensity decay: <97 |
1920 independent reflections |
R[F2 > 2σ(F2)] = 0.035 | 2 restraints |
wR(F2) = 0.071 | All H-atom parameters refined |
S = 1.02 | Δρmax = 0.11 e Å−3 |
1920 reflections | Δρmin = −0.10 e Å−3 |
343 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | 1.38687 (18) | 0.3314 (9) | 1.4166 (3) | 0.0875 (12) | |
N2 | 1.21014 (14) | −0.0157 (6) | 1.1031 (2) | 0.0585 (8) | |
N3 | 0.74195 (14) | 0.1956 (5) | 0.6940 (2) | 0.0434 (7) | |
N4 | 0.60546 (19) | 0.7947 (7) | 0.4941 (3) | 0.0774 (10) | |
C1 | 1.3264 (2) | 0.1870 (10) | 1.3719 (3) | 0.0736 (12) | |
C2 | 1.4176 (2) | 0.4898 (11) | 1.3394 (5) | 0.0833 (13) | |
C3 | 1.3924 (2) | 0.5013 (10) | 1.2211 (4) | 0.0753 (12) | |
C4 | 1.3322 (2) | 0.3496 (9) | 1.1778 (4) | 0.0656 (10) | |
C5 | 1.29817 (17) | 0.1853 (8) | 1.2537 (3) | 0.0558 (9) | |
C6 | 1.23284 (18) | 0.0183 (8) | 1.2119 (3) | 0.0589 (9) | |
C7 | 1.14446 (17) | −0.1646 (7) | 1.0697 (3) | 0.0515 (9) | |
C8 | 1.1390 (2) | −0.3547 (9) | 0.9741 (3) | 0.0620 (10) | |
C9 | 1.07583 (19) | −0.4965 (9) | 0.9364 (3) | 0.0590 (9) | |
C10 | 1.01474 (16) | −0.4492 (6) | 0.9883 (3) | 0.0449 (8) | |
C11 | 1.01964 (19) | −0.2567 (7) | 1.0809 (3) | 0.0493 (8) | |
C12 | 1.08326 (19) | −0.1167 (8) | 1.1219 (3) | 0.0506 (8) | |
C13 | 0.94456 (19) | −0.5996 (8) | 0.9437 (3) | 0.0502 (9) | |
C14 | 0.88863 (15) | −0.3967 (6) | 0.8794 (3) | 0.0409 (8) | |
C15 | 0.89570 (18) | −0.2901 (7) | 0.7680 (3) | 0.0473 (8) | |
C16 | 0.84642 (17) | −0.1021 (7) | 0.7103 (3) | 0.0448 (8) | |
C17 | 0.78862 (16) | −0.0037 (6) | 0.7618 (3) | 0.0383 (7) | |
C18 | 0.78076 (18) | −0.1103 (7) | 0.8731 (3) | 0.0445 (8) | |
C19 | 0.82977 (16) | −0.3062 (7) | 0.9295 (3) | 0.0417 (8) | |
C20 | 0.69408 (18) | 0.3254 (7) | 0.7398 (3) | 0.0459 (8) | |
C21 | 0.64497 (16) | 0.5350 (7) | 0.6741 (3) | 0.0440 (8) | |
C22 | 0.59340 (19) | 0.6733 (8) | 0.7285 (4) | 0.0635 (10) | |
C23 | 0.5481 (2) | 0.8671 (9) | 0.6633 (4) | 0.0695 (12) | |
C24 | 0.5556 (2) | 0.9178 (9) | 0.5486 (4) | 0.0665 (12) | |
C25 | 0.6488 (2) | 0.6058 (8) | 0.5587 (3) | 0.0608 (10) | |
H16 | 0.8509 (15) | −0.025 (7) | 0.634 (3) | 0.046 (8)* | |
H15 | 0.9368 (17) | −0.346 (7) | 0.738 (3) | 0.054 (9)* | |
H18 | 0.7402 (13) | −0.058 (6) | 0.910 (2) | 0.030 (7)* | |
H24 | 0.5257 (15) | 1.058 (7) | 0.507 (3) | 0.046 (9)* | |
H13B | 0.9250 (16) | −0.695 (7) | 1.012 (3) | 0.059 (9)* | |
H25 | 0.686 (2) | 0.504 (8) | 0.509 (3) | 0.089 (12)* | |
H13A | 0.9534 (15) | −0.754 (7) | 0.891 (3) | 0.047 (9)* | |
H11 | 0.9790 (15) | −0.233 (6) | 1.116 (2) | 0.033 (8)* | |
H9 | 1.0757 (19) | −0.618 (8) | 0.872 (3) | 0.079 (12)* | |
H2 | 1.464 (2) | 0.605 (10) | 1.368 (4) | 0.109 (15)* | |
H8 | 1.182 (2) | −0.369 (8) | 0.939 (3) | 0.079 (12)* | |
H23 | 0.514 (2) | 0.973 (9) | 0.703 (4) | 0.091 (13)* | |
H20 | 0.6855 (19) | 0.281 (8) | 0.825 (4) | 0.083 (11)* | |
H1 | 1.3054 (18) | 0.053 (8) | 1.429 (3) | 0.070 (11)* | |
H4 | 1.314 (2) | 0.339 (8) | 1.102 (3) | 0.079 (13)* | |
H12 | 1.0836 (15) | 0.016 (6) | 1.184 (3) | 0.042 (8)* | |
H19 | 0.8250 (16) | −0.393 (6) | 1.007 (3) | 0.059 (9)* | |
H6 | 1.207 (2) | −0.095 (8) | 1.273 (3) | 0.085 (12)* | |
H22 | 0.5898 (18) | 0.630 (7) | 0.813 (3) | 0.074 (11)* | |
H3 | 1.414 (2) | 0.625 (8) | 1.174 (4) | 0.082 (14)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.065 (2) | 0.123 (3) | 0.070 (2) | −0.004 (2) | −0.0091 (19) | −0.024 (2) |
N2 | 0.0473 (16) | 0.0663 (18) | 0.0593 (19) | −0.0064 (15) | −0.0009 (14) | −0.0007 (15) |
N3 | 0.0451 (15) | 0.0446 (16) | 0.0409 (15) | 0.0044 (13) | 0.0073 (13) | 0.0003 (13) |
N4 | 0.091 (3) | 0.085 (2) | 0.053 (2) | 0.035 (2) | −0.0018 (19) | 0.0046 (18) |
C1 | 0.061 (3) | 0.100 (3) | 0.060 (2) | 0.005 (2) | 0.007 (2) | −0.004 (2) |
C2 | 0.056 (2) | 0.092 (3) | 0.099 (4) | −0.012 (3) | 0.001 (3) | −0.026 (3) |
C3 | 0.057 (2) | 0.081 (3) | 0.087 (3) | −0.009 (2) | 0.008 (2) | −0.007 (3) |
C4 | 0.057 (2) | 0.077 (3) | 0.059 (2) | −0.005 (2) | −0.0021 (19) | −0.006 (2) |
C5 | 0.044 (2) | 0.067 (2) | 0.055 (2) | 0.0040 (17) | 0.0014 (16) | −0.0020 (19) |
C6 | 0.054 (2) | 0.060 (2) | 0.060 (3) | −0.0026 (19) | 0.0038 (19) | 0.0053 (19) |
C7 | 0.0447 (19) | 0.055 (2) | 0.052 (2) | 0.0002 (18) | −0.0016 (16) | 0.0051 (18) |
C8 | 0.048 (2) | 0.080 (3) | 0.058 (2) | −0.003 (2) | 0.0109 (18) | −0.007 (2) |
C9 | 0.060 (2) | 0.067 (2) | 0.049 (2) | 0.002 (2) | 0.0032 (18) | −0.0112 (19) |
C10 | 0.053 (2) | 0.0359 (17) | 0.0440 (17) | 0.0036 (15) | −0.0003 (15) | 0.0070 (15) |
C11 | 0.048 (2) | 0.049 (2) | 0.052 (2) | 0.0024 (16) | 0.0088 (16) | 0.0018 (17) |
C12 | 0.054 (2) | 0.048 (2) | 0.048 (2) | −0.0002 (17) | 0.0000 (17) | −0.0053 (17) |
C13 | 0.058 (2) | 0.0415 (19) | 0.048 (2) | −0.0005 (17) | −0.0035 (17) | 0.0029 (17) |
C14 | 0.0438 (18) | 0.0362 (17) | 0.0404 (17) | −0.0084 (15) | −0.0016 (14) | 0.0019 (15) |
C15 | 0.047 (2) | 0.048 (2) | 0.048 (2) | 0.0042 (16) | 0.0116 (16) | 0.0014 (16) |
C16 | 0.055 (2) | 0.0472 (19) | 0.0329 (17) | 0.0066 (16) | 0.0084 (15) | 0.0035 (15) |
C17 | 0.0441 (17) | 0.0348 (15) | 0.0353 (16) | −0.0039 (14) | 0.0033 (14) | −0.0006 (14) |
C18 | 0.0471 (19) | 0.0464 (19) | 0.0415 (19) | −0.0003 (16) | 0.0112 (16) | 0.0003 (16) |
C19 | 0.050 (2) | 0.0416 (18) | 0.0322 (17) | −0.0057 (15) | 0.0026 (14) | 0.0033 (15) |
C20 | 0.054 (2) | 0.0423 (18) | 0.0417 (19) | 0.0000 (17) | 0.0075 (17) | 0.0003 (16) |
C21 | 0.0411 (17) | 0.0433 (18) | 0.047 (2) | 0.0014 (15) | 0.0046 (15) | −0.0039 (16) |
C22 | 0.062 (2) | 0.066 (2) | 0.066 (3) | 0.011 (2) | 0.021 (2) | 0.010 (2) |
C23 | 0.054 (2) | 0.062 (2) | 0.094 (3) | 0.017 (2) | 0.019 (2) | 0.009 (2) |
C24 | 0.064 (3) | 0.055 (2) | 0.072 (3) | 0.009 (2) | −0.018 (2) | 0.002 (2) |
C25 | 0.076 (3) | 0.062 (2) | 0.043 (2) | 0.018 (2) | 0.0051 (19) | −0.0015 (19) |
N1—C2 | 1.339 (6) | C11—C12 | 1.379 (5) |
N1—C1 | 1.351 (5) | C11—H11 | 0.92 (3) |
N2—C6 | 1.259 (4) | C12—H12 | 0.93 (3) |
N2—C7 | 1.415 (4) | C13—C14 | 1.516 (4) |
N3—C20 | 1.256 (3) | C13—H13B | 1.01 (4) |
N3—C17 | 1.421 (4) | C13—H13A | 0.97 (3) |
N4—C24 | 1.325 (5) | C14—C19 | 1.380 (4) |
N4—C25 | 1.340 (5) | C14—C15 | 1.386 (4) |
C1—C5 | 1.373 (5) | C15—C16 | 1.367 (5) |
C1—H1 | 1.02 (4) | C15—H15 | 0.93 (3) |
C2—C3 | 1.362 (6) | C16—C17 | 1.383 (4) |
C2—H2 | 1.03 (5) | C16—H16 | 0.96 (3) |
C3—C4 | 1.361 (5) | C17—C18 | 1.388 (4) |
C3—H3 | 0.92 (4) | C18—C19 | 1.382 (4) |
C4—C5 | 1.377 (5) | C18—H18 | 0.95 (3) |
C4—H4 | 0.88 (4) | C19—H19 | 0.98 (3) |
C5—C6 | 1.469 (4) | C20—C21 | 1.467 (4) |
C6—H6 | 1.05 (4) | C20—H20 | 1.03 (4) |
C7—C12 | 1.385 (5) | C21—C25 | 1.367 (5) |
C7—C8 | 1.393 (5) | C21—C22 | 1.381 (5) |
C8—C9 | 1.369 (5) | C22—C23 | 1.377 (5) |
C8—H8 | 0.96 (4) | C22—H22 | 1.00 (4) |
C9—C10 | 1.381 (4) | C23—C24 | 1.355 (6) |
C9—H9 | 0.93 (4) | C23—H23 | 0.98 (4) |
C10—C11 | 1.375 (5) | C24—H24 | 0.94 (3) |
C10—C13 | 1.511 (5) | C25—H25 | 1.07 (4) |
C2—N1—C1 | 116.2 (4) | C10—C13—H13B | 109.7 (18) |
C6—N2—C7 | 118.8 (3) | C14—C13—H13B | 109.9 (18) |
C20—N3—C17 | 120.5 (2) | C10—C13—H13A | 109.4 (17) |
C24—N4—C25 | 116.0 (4) | C14—C13—H13A | 109.1 (18) |
N1—C1—C5 | 123.7 (4) | H13B—C13—H13A | 106 (3) |
N1—C1—H1 | 116.5 (19) | C19—C14—C15 | 117.3 (3) |
C5—C1—H1 | 119 (2) | C19—C14—C13 | 121.9 (3) |
N1—C2—C3 | 123.4 (4) | C15—C14—C13 | 120.8 (3) |
N1—C2—H2 | 120 (2) | C16—C15—C14 | 121.3 (3) |
C3—C2—H2 | 117 (3) | C16—C15—H15 | 122.6 (19) |
C4—C3—C2 | 119.2 (5) | C14—C15—H15 | 116.0 (19) |
C4—C3—H3 | 121 (3) | C15—C16—C17 | 121.6 (3) |
C2—C3—H3 | 119 (3) | C15—C16—H16 | 122.2 (18) |
C3—C4—C5 | 119.7 (4) | C17—C16—H16 | 116.1 (18) |
C3—C4—H4 | 125 (3) | C16—C17—C18 | 117.6 (3) |
C5—C4—H4 | 116 (3) | C16—C17—N3 | 116.3 (3) |
C1—C5—C4 | 117.7 (4) | C18—C17—N3 | 126.1 (3) |
C1—C5—C6 | 120.3 (4) | C19—C18—C17 | 120.5 (3) |
C4—C5—C6 | 122.0 (3) | C19—C18—H18 | 118.6 (16) |
N2—C6—C5 | 122.1 (3) | C17—C18—H18 | 120.8 (16) |
N2—C6—H6 | 118 (2) | C14—C19—C18 | 121.7 (3) |
C5—C6—H6 | 120 (2) | C14—C19—H19 | 115.3 (18) |
C12—C7—C8 | 117.8 (3) | C18—C19—H19 | 123.0 (18) |
C12—C7—N2 | 123.3 (3) | N3—C20—C21 | 122.7 (3) |
C8—C7—N2 | 118.8 (3) | N3—C20—H20 | 121 (2) |
C9—C8—C7 | 120.8 (4) | C21—C20—H20 | 116 (2) |
C9—C8—H8 | 126 (2) | C25—C21—C22 | 117.3 (3) |
C7—C8—H8 | 113 (2) | C25—C21—C20 | 122.2 (3) |
C8—C9—C10 | 121.5 (4) | C22—C21—C20 | 120.5 (3) |
C8—C9—H9 | 116 (2) | C23—C22—C21 | 118.6 (4) |
C10—C9—H9 | 122 (2) | C23—C22—H22 | 122 (2) |
C11—C10—C9 | 117.7 (3) | C21—C22—H22 | 119 (2) |
C11—C10—C13 | 121.0 (3) | C24—C23—C22 | 119.3 (4) |
C9—C10—C13 | 121.2 (3) | C24—C23—H23 | 122 (2) |
C10—C11—C12 | 121.6 (3) | C22—C23—H23 | 118 (2) |
C10—C11—H11 | 116.5 (17) | N4—C24—C23 | 123.8 (4) |
C12—C11—H11 | 121.9 (17) | N4—C24—H24 | 118.1 (19) |
C11—C12—C7 | 120.6 (3) | C23—C24—H24 | 118.0 (18) |
C11—C12—H12 | 118.4 (18) | N4—C25—C21 | 124.9 (4) |
C7—C12—H12 | 121.0 (18) | N4—C25—H25 | 113 (2) |
C10—C13—C14 | 112.5 (3) | C21—C25—H25 | 122 (2) |
C2—N1—C1—C5 | 3.1 (6) | C10—C13—C14—C19 | −106.9 (3) |
C1—N1—C2—C3 | −2.4 (7) | C10—C13—C14—C15 | 71.8 (4) |
N1—C2—C3—C4 | 1.3 (7) | C19—C14—C15—C16 | 0.2 (4) |
C2—C3—C4—C5 | −0.6 (6) | C13—C14—C15—C16 | −178.5 (3) |
N1—C1—C5—C4 | −2.6 (6) | C14—C15—C16—C17 | 1.9 (5) |
N1—C1—C5—C6 | 178.9 (3) | C15—C16—C17—C18 | −2.2 (5) |
C3—C4—C5—C1 | 1.2 (6) | C15—C16—C17—N3 | 178.8 (3) |
C3—C4—C5—C6 | 179.7 (4) | C20—N3—C17—C16 | −170.3 (3) |
C7—N2—C6—C5 | −176.2 (3) | C20—N3—C17—C18 | 10.7 (4) |
C1—C5—C6—N2 | −171.6 (4) | C16—C17—C18—C19 | 0.5 (4) |
C4—C5—C6—N2 | 10.0 (5) | N3—C17—C18—C19 | 179.4 (3) |
C6—N2—C7—C12 | 44.3 (5) | C15—C14—C19—C18 | −1.9 (4) |
C6—N2—C7—C8 | −140.4 (3) | C13—C14—C19—C18 | 176.8 (3) |
C12—C7—C8—C9 | −2.3 (5) | C17—C18—C19—C14 | 1.6 (5) |
N2—C7—C8—C9 | −178.0 (4) | C17—N3—C20—C21 | 179.4 (3) |
C7—C8—C9—C10 | 2.4 (6) | N3—C20—C21—C25 | −0.9 (5) |
C8—C9—C10—C11 | −0.9 (5) | N3—C20—C21—C22 | −179.7 (3) |
C8—C9—C10—C13 | 178.1 (3) | C25—C21—C22—C23 | 1.6 (5) |
C9—C10—C11—C12 | −0.6 (5) | C20—C21—C22—C23 | −179.6 (3) |
C13—C10—C11—C12 | −179.6 (3) | C21—C22—C23—C24 | −0.4 (6) |
C10—C11—C12—C7 | 0.6 (5) | C25—N4—C24—C23 | 1.5 (6) |
C8—C7—C12—C11 | 0.8 (5) | C22—C23—C24—N4 | −1.2 (6) |
N2—C7—C12—C11 | 176.3 (3) | C24—N4—C25—C21 | −0.2 (6) |
C11—C10—C13—C14 | 70.4 (4) | C22—C21—C25—N4 | −1.3 (6) |
C9—C10—C13—C14 | −108.6 (4) | C20—C21—C25—N4 | 179.9 (4) |
Experimental details
Crystal data | |
Chemical formula | C25H20N4 |
Mr | 376.45 |
Crystal system, space group | Monoclinic, Pc |
Temperature (K) | 293 |
a, b, c (Å) | 18.7505 (10), 4.6414 (10), 11.3866 (10) |
β (°) | 98.394 (10) |
V (Å3) | 980.3 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.4 × 0.35 × 0.26 |
Data collection | |
Diffractometer | Enraf Nonius CAD-4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.956, 0.980 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3793, 1920, 1287 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.071, 1.02 |
No. of reflections | 1920 |
No. of parameters | 343 |
No. of restraints | 2 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.11, −0.10 |
Computer programs: CAD-4 EXPRESS (Enraf-Nonius, 1994), CAD-4 EXPRESS, XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXL97, Please provide missing information.
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Rigid bipyridyl-type bidentate Schiff base ligands have been intensively utilized in order to assemble various coordination polymers with intriguing topology (Barnett & Champness, 2003; Su et al., 2004), while angular chelating bipyridyl Schiff base ligands are known to form helical complexes (Guo et al., 2002). However, angular ditopic Schiff base ligands containing non-chelating dipyridyl groups have rarely been used to construct coordination assemblies. As a continuation of our study of the coordination chemistry of semi-rigid ligands (Su et al., 2003; Chen et al., 2002), we have synthesized the title compound, (I), and report its single-crystal structure.
Compound (I) crystallizes in the non-centrosymmetric space group Pc, which was confirmed by the routine PLUTON ADDSYM check (Spek, 1990, 2003). As expected, the two rigid parts incorporating the 3-pyridyl groups adopt an angular arrangement (Fig. 1). The dihedral angle between the two phenyl rings linked by the methylene is 77.95 (16)°, which determines the specific orientation of the pyridyl groups. However, the pyridyl rings are not exactly coplanar with the phenyl rings, although the coplanar conformation is energetically preferred (Su et al., 2000). On one side of the methylene group, the pyridyl (C21–C25/N4) and phenyl (C14–C19) rings are nearly coplanar, with a dihedral angle of 9.95 (17)°, but on the other side, these two rings (C7–C12 for the phenyl ring and C1–C5/N1 for the pyridyl ring) adopt a dihedral angle of 53.86 (18)°, significantly deviating from the mean plane. Such asymmetric disposition of the two rigid branches may account for the absence of centrosymmetry in the crystal.
Analysis of the crystal-packing mode reveals that the ligands stack up in the crystal lattice with each six-membered ring (both phenyl and pyridyl) parallel to its counterpart in adjacent ligands, giving a centroid-to-centroid distance of ca 4.64 Å. As shown in Fig. 2, the overlapping arrangement of the ligands results in a one-dimensional array along the b axis, which is sustained by forming π–π intermolecular interactions. Such arrays are aligned parallel to each other, to form two-dimensional layers along the c axis. When viewed along the c axis (Fig. 3), it is clear that the one-dimensional parallel arrays run in opposite directions. That is, the arrowheaded methylene groups point in the same direction in one array but in the opposite direction in adjacent arrays. The whole crystal is stacked up into two-dimensional layers of ca 19 Å width, which are composed of the alternately opposite-running one-dimensional arrays.