Acta Cryst. (2012). E68, o40 [ doi:10.1107/S1600536811051257 ]
In the title molecule, C30H36N2O2, the dihedral angles between the central benzene ring and the two benzene rings of the butylsalicylaldimine groups are 14.3 (2) and 40.6 (2)°. There are two strong intramolecular O-H
N hydrogen bonds which form S(6) rings. The crystal studied was a non-merohedral twin with refined components of 0.270 (4) and 0.730 (4).
5-methyl-3-t-butyl-2-hydroxybenzaldehyde (0.192 g, 1 mmol) dissolved in 20 ml ethanol, then 1,2-phenylenediamine (0.043 g, 0.5 mmol) in 20 ml ethanol was added. The mixture was stirred at 323K for 5 h. The solution was cooled to room temperature and the resulting orange solid was collected, washed by cold ethanol and dried in vacuo. Yield: 0.175 g, 80.6%. Cooling the ethanol solution to room temperature gave orange crystals suitable for X-ray diffraction measurement.
All H atoms were positioned geometrically and refined using a riding model with C—H = 0.93–0.97 Å; O—H = 0.82Å and with Uiso(H) = 1.2 times Ueq(C) or Uiso(H) = 1.5 times Ueq(Cmethyl,O). Analysis of the structure in PLATON (Spek, 2009) revealed the crystal was a non-merohedral twin with twin law (110)[432]. The ratio of the twin components refined to 0.270 (4):0.730 (4).
Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
![[Figure 1]](./lh5371fig1thm.gif)
| Fig. 1. The molecular structure of title compound. Displacement ellipsoids are drawn at the 50% probability level. |
| C30H36N2O2 | Z = 2 |
| Mr = 456.61 | F(000) = 492 |
| Triclinic, P1 | Dx = 1.158 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 10.578 (7) Å | Cell parameters from 3022 reflections |
| b = 11.394 (7) Å | θ = 2.4–24.5° |
| c = 12.217 (7) Å | µ = 0.07 mm−1 |
| α = 72.195 (6)° | T = 296 K |
| β = 73.525 (6)° | Block, orange |
| γ = 72.975 (6)° | 0.28 × 0.22 × 0.15 mm |
| V = 1309.8 (14) Å3 |
| Bruker SMART CCD diffractometer | 4593 independent reflections |
| Radiation source: fine-focus sealed tube | 2894 reflections with I > 2σ(I) |
| graphite | Rint = 0.000 |
| φ and ω scans | θmax = 25.0°, θmin = 2.4° |
| Absorption correction: multi-scan (SADABS; Bruker, 2007) | h = −12→12 |
| Tmin = 0.980, Tmax = 0.989 | k = −13→13 |
| 4593 measured reflections | l = −13→14 |
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.075 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.271 | H-atom parameters constrained |
| S = 1.13 | w = 1/[σ2(Fo2) + (0.1477P)2 + 0.0358P] where P = (Fo2 + 2Fc2)/3 |
| 4593 reflections | (Δ/σ)max = 0.001 |
| 318 parameters | Δρmax = 0.29 e Å−3 |
| 0 restraints | Δρmin = −0.30 e Å−3 |
| C30H36N2O2 | γ = 72.975 (6)° |
| Mr = 456.61 | V = 1309.8 (14) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 10.578 (7) Å | Mo Kα radiation |
| b = 11.394 (7) Å | µ = 0.07 mm−1 |
| c = 12.217 (7) Å | T = 296 K |
| α = 72.195 (6)° | 0.28 × 0.22 × 0.15 mm |
| β = 73.525 (6)° |
| Bruker SMART CCD diffractometer | 4593 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2007) | 2894 reflections with I > 2σ(I) |
| Tmin = 0.980, Tmax = 0.989 | Rint = 0.000 |
| 4593 measured reflections | θmax = 25.0° |
| R[F2 > 2σ(F2)] = 0.075 | H-atom parameters constrained |
| wR(F2) = 0.271 | Δρmax = 0.29 e Å−3 |
| S = 1.13 | Δρmin = −0.30 e Å−3 |
| 4593 reflections | Absolute structure: ? |
| 318 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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 | 0.2830 (3) | 0.5924 (3) | 0.9145 (3) | 0.0503 (7) | |
| N2 | 0.4261 (3) | 0.7498 (3) | 0.7380 (2) | 0.0519 (8) | |
| O1 | 0.0609 (2) | 0.7680 (2) | 0.9079 (2) | 0.0631 (8) | |
| H1 | 0.1431 | 0.7403 | 0.8950 | 0.095* | |
| O2 | 0.2253 (2) | 0.9257 (2) | 0.6653 (3) | 0.0643 (8) | |
| H2 | 0.2684 | 0.8546 | 0.6911 | 0.096* | |
| C1 | 0.4186 (3) | 0.5407 (3) | 0.8651 (3) | 0.0481 (9) | |
| C2 | 0.4834 (4) | 0.4144 (4) | 0.8975 (4) | 0.0618 (10) | |
| H2A | 0.4367 | 0.3594 | 0.9571 | 0.074* | |
| C3 | 0.6136 (4) | 0.3682 (4) | 0.8448 (4) | 0.0673 (11) | |
| H3 | 0.6542 | 0.2829 | 0.8682 | 0.081* | |
| C4 | 0.6842 (4) | 0.4480 (4) | 0.7573 (4) | 0.0667 (11) | |
| H4 | 0.7729 | 0.4171 | 0.7213 | 0.080* | |
| C5 | 0.6236 (4) | 0.5733 (4) | 0.7231 (3) | 0.0616 (10) | |
| H5 | 0.6717 | 0.6269 | 0.6632 | 0.074* | |
| C6 | 0.4910 (3) | 0.6220 (3) | 0.7765 (3) | 0.0494 (9) | |
| C7 | 0.2184 (3) | 0.5328 (3) | 1.0093 (3) | 0.0513 (9) | |
| H7 | 0.2646 | 0.4556 | 1.0486 | 0.062* | |
| C8 | 0.0780 (3) | 0.5772 (3) | 1.0597 (3) | 0.0474 (8) | |
| C9 | 0.0143 (4) | 0.5004 (3) | 1.1613 (3) | 0.0507 (9) | |
| H9 | 0.0650 | 0.4232 | 1.1960 | 0.061* | |
| C10 | −0.1199 (3) | 0.5353 (3) | 1.2109 (3) | 0.0479 (8) | |
| C11 | −0.1908 (3) | 0.6540 (3) | 1.1575 (3) | 0.0462 (8) | |
| H11 | −0.2815 | 0.6801 | 1.1916 | 0.055* | |
| C12 | −0.1352 (3) | 0.7354 (3) | 1.0573 (3) | 0.0443 (8) | |
| C13 | 0.0023 (3) | 0.6937 (3) | 1.0077 (3) | 0.0473 (8) | |
| C14 | −0.1909 (4) | 0.4504 (4) | 1.3160 (3) | 0.0625 (10) | |
| H14A | −0.1396 | 0.3646 | 1.3231 | 0.094* | |
| H14B | −0.2794 | 0.4561 | 1.3060 | 0.094* | |
| H14C | −0.1988 | 0.4763 | 1.3858 | 0.094* | |
| C15 | −0.2195 (3) | 0.8652 (3) | 1.0034 (3) | 0.0493 (9) | |
| C16 | −0.3626 (4) | 0.8925 (4) | 1.0780 (4) | 0.0667 (11) | |
| H16A | −0.3579 | 0.8885 | 1.1564 | 0.100* | |
| H16B | −0.4093 | 0.8308 | 1.0805 | 0.100* | |
| H16C | −0.4105 | 0.9754 | 1.0440 | 0.100* | |
| C17 | −0.1554 (4) | 0.9714 (4) | 0.9985 (4) | 0.0663 (11) | |
| H17A | −0.2100 | 1.0516 | 0.9665 | 0.099* | |
| H17B | −0.0662 | 0.9608 | 0.9494 | 0.099* | |
| H17C | −0.1499 | 0.9684 | 1.0764 | 0.099* | |
| C18 | −0.2286 (4) | 0.8684 (4) | 0.8795 (3) | 0.0718 (12) | |
| H18A | −0.2766 | 0.9509 | 0.8444 | 0.108* | |
| H18B | −0.2759 | 0.8062 | 0.8843 | 0.108* | |
| H18C | −0.1391 | 0.8502 | 0.8322 | 0.108* | |
| C19 | 0.4916 (3) | 0.8371 (4) | 0.7072 (3) | 0.0520 (9) | |
| H19 | 0.5806 | 0.8146 | 0.7161 | 0.062* | |
| C20 | 0.4349 (3) | 0.9685 (3) | 0.6595 (3) | 0.0473 (8) | |
| C21 | 0.5145 (3) | 1.0562 (4) | 0.6317 (3) | 0.0538 (9) | |
| H21 | 0.6034 | 1.0280 | 0.6413 | 0.065* | |
| C22 | 0.4643 (3) | 1.1837 (4) | 0.5903 (3) | 0.0515 (9) | |
| C23 | 0.3297 (3) | 1.2211 (3) | 0.5787 (3) | 0.0509 (9) | |
| H23 | 0.2936 | 1.3072 | 0.5537 | 0.061* | |
| C24 | 0.2463 (3) | 1.1391 (3) | 0.6016 (3) | 0.0459 (8) | |
| C25 | 0.3013 (3) | 1.0107 (3) | 0.6425 (3) | 0.0471 (8) | |
| C26 | 0.5487 (4) | 1.2799 (4) | 0.5618 (4) | 0.0772 (12) | |
| H26A | 0.5223 | 1.3229 | 0.6240 | 0.116* | |
| H26B | 0.5349 | 1.3402 | 0.4892 | 0.116* | |
| H26C | 0.6426 | 1.2377 | 0.5541 | 0.116* | |
| C27 | 0.1000 (3) | 1.1870 (3) | 0.5839 (3) | 0.0521 (9) | |
| C28 | −0.0004 (4) | 1.1451 (4) | 0.6987 (4) | 0.0799 (14) | |
| H28A | −0.0906 | 1.1728 | 0.6849 | 0.120* | |
| H28B | 0.0051 | 1.1817 | 0.7578 | 0.120* | |
| H28C | 0.0216 | 1.0545 | 0.7251 | 0.120* | |
| C29 | 0.0872 (4) | 1.1343 (4) | 0.4862 (4) | 0.0758 (13) | |
| H29A | 0.1115 | 1.0435 | 0.5082 | 0.114* | |
| H29B | 0.1466 | 1.1647 | 0.4139 | 0.114* | |
| H29C | −0.0044 | 1.1618 | 0.4759 | 0.114* | |
| C30 | 0.0582 (4) | 1.3314 (4) | 0.5466 (4) | 0.0647 (11) | |
| H30A | −0.0328 | 1.3563 | 0.5348 | 0.097* | |
| H30B | 0.1181 | 1.3618 | 0.4746 | 0.097* | |
| H30C | 0.0631 | 1.3666 | 0.6069 | 0.097* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| N1 | 0.0436 (15) | 0.0505 (18) | 0.0563 (18) | −0.0057 (13) | −0.0101 (14) | −0.0173 (15) |
| N2 | 0.0491 (16) | 0.0522 (19) | 0.0444 (16) | −0.0018 (15) | −0.0067 (13) | −0.0099 (14) |
| O1 | 0.0528 (14) | 0.0578 (17) | 0.0587 (16) | −0.0115 (12) | 0.0020 (12) | 0.0004 (13) |
| O2 | 0.0534 (15) | 0.0452 (15) | 0.087 (2) | −0.0099 (12) | −0.0198 (14) | −0.0028 (14) |
| C1 | 0.0416 (18) | 0.051 (2) | 0.054 (2) | −0.0017 (16) | −0.0157 (16) | −0.0193 (17) |
| C2 | 0.059 (2) | 0.048 (2) | 0.074 (3) | −0.0061 (18) | −0.0136 (19) | −0.0160 (19) |
| C3 | 0.062 (2) | 0.051 (2) | 0.085 (3) | 0.006 (2) | −0.024 (2) | −0.022 (2) |
| C4 | 0.048 (2) | 0.070 (3) | 0.073 (3) | 0.011 (2) | −0.0123 (19) | −0.029 (2) |
| C5 | 0.050 (2) | 0.066 (3) | 0.055 (2) | 0.0009 (19) | −0.0050 (17) | −0.0155 (19) |
| C6 | 0.0471 (19) | 0.054 (2) | 0.0427 (19) | 0.0037 (16) | −0.0139 (15) | −0.0156 (16) |
| C7 | 0.051 (2) | 0.050 (2) | 0.054 (2) | −0.0072 (17) | −0.0147 (17) | −0.0160 (17) |
| C8 | 0.0481 (19) | 0.050 (2) | 0.0460 (19) | −0.0087 (16) | −0.0132 (15) | −0.0144 (16) |
| C9 | 0.057 (2) | 0.047 (2) | 0.048 (2) | −0.0074 (16) | −0.0198 (16) | −0.0065 (16) |
| C10 | 0.055 (2) | 0.051 (2) | 0.0390 (17) | −0.0168 (17) | −0.0150 (15) | −0.0042 (15) |
| C11 | 0.0444 (18) | 0.055 (2) | 0.0429 (19) | −0.0156 (16) | −0.0097 (14) | −0.0127 (16) |
| C12 | 0.0442 (18) | 0.048 (2) | 0.0417 (18) | −0.0101 (15) | −0.0112 (14) | −0.0108 (15) |
| C13 | 0.0501 (19) | 0.050 (2) | 0.0397 (17) | −0.0143 (16) | −0.0068 (15) | −0.0072 (15) |
| C14 | 0.068 (2) | 0.064 (3) | 0.052 (2) | −0.025 (2) | −0.0168 (18) | 0.0032 (18) |
| C15 | 0.0489 (19) | 0.049 (2) | 0.0466 (19) | −0.0091 (16) | −0.0141 (15) | −0.0057 (16) |
| C16 | 0.053 (2) | 0.062 (3) | 0.075 (3) | −0.0029 (19) | −0.0141 (19) | −0.012 (2) |
| C17 | 0.068 (2) | 0.047 (2) | 0.084 (3) | −0.0155 (19) | −0.020 (2) | −0.010 (2) |
| C18 | 0.083 (3) | 0.073 (3) | 0.058 (2) | −0.005 (2) | −0.031 (2) | −0.011 (2) |
| C19 | 0.0457 (19) | 0.057 (2) | 0.0437 (19) | −0.0007 (18) | −0.0059 (15) | −0.0124 (17) |
| C20 | 0.0424 (18) | 0.055 (2) | 0.0398 (17) | −0.0069 (16) | −0.0041 (14) | −0.0138 (15) |
| C21 | 0.0453 (19) | 0.068 (3) | 0.049 (2) | −0.0123 (18) | −0.0056 (16) | −0.0206 (18) |
| C22 | 0.053 (2) | 0.058 (2) | 0.0451 (19) | −0.0205 (18) | −0.0026 (16) | −0.0152 (17) |
| C23 | 0.059 (2) | 0.047 (2) | 0.0417 (18) | −0.0128 (17) | −0.0026 (16) | −0.0112 (15) |
| C24 | 0.0469 (18) | 0.047 (2) | 0.0397 (18) | −0.0097 (16) | −0.0056 (14) | −0.0086 (15) |
| C25 | 0.0437 (18) | 0.051 (2) | 0.0442 (18) | −0.0128 (16) | −0.0042 (14) | −0.0111 (15) |
| C26 | 0.078 (3) | 0.083 (3) | 0.081 (3) | −0.040 (2) | −0.009 (2) | −0.021 (2) |
| C27 | 0.0487 (19) | 0.045 (2) | 0.055 (2) | −0.0066 (16) | −0.0099 (16) | −0.0072 (16) |
| C28 | 0.049 (2) | 0.074 (3) | 0.086 (3) | −0.008 (2) | −0.001 (2) | 0.007 (2) |
| C29 | 0.072 (3) | 0.068 (3) | 0.100 (3) | −0.007 (2) | −0.038 (2) | −0.027 (2) |
| C30 | 0.062 (2) | 0.049 (2) | 0.073 (3) | −0.0042 (18) | −0.016 (2) | −0.0084 (19) |
| N1—C7 | 1.270 (4) | C16—H16A | 0.9600 |
| N1—C1 | 1.414 (4) | C16—H16B | 0.9600 |
| N2—C19 | 1.280 (5) | C16—H16C | 0.9600 |
| N2—C6 | 1.411 (4) | C17—H17A | 0.9600 |
| O1—C13 | 1.354 (4) | C17—H17B | 0.9600 |
| O1—H1 | 0.8200 | C17—H17C | 0.9600 |
| O2—C25 | 1.351 (4) | C18—H18A | 0.9600 |
| O2—H2 | 0.8200 | C18—H18B | 0.9600 |
| C1—C2 | 1.387 (5) | C18—H18C | 0.9600 |
| C1—C6 | 1.396 (5) | C19—C20 | 1.441 (5) |
| C2—C3 | 1.368 (5) | C19—H19 | 0.9300 |
| C2—H2A | 0.9300 | C20—C21 | 1.395 (5) |
| C3—C4 | 1.370 (6) | C20—C25 | 1.407 (5) |
| C3—H3 | 0.9300 | C21—C22 | 1.378 (5) |
| C4—C5 | 1.370 (6) | C21—H21 | 0.9300 |
| C4—H4 | 0.9300 | C22—C23 | 1.397 (5) |
| C5—C6 | 1.395 (5) | C22—C26 | 1.511 (5) |
| C5—H5 | 0.9300 | C23—C24 | 1.382 (5) |
| C7—C8 | 1.440 (5) | C23—H23 | 0.9300 |
| C7—H7 | 0.9300 | C24—C25 | 1.396 (5) |
| C8—C13 | 1.399 (5) | C24—C27 | 1.536 (5) |
| C8—C9 | 1.403 (5) | C26—H26A | 0.9600 |
| C9—C10 | 1.367 (5) | C26—H26B | 0.9600 |
| C9—H9 | 0.9300 | C26—H26C | 0.9600 |
| C10—C11 | 1.401 (5) | C27—C30 | 1.529 (5) |
| C10—C14 | 1.505 (5) | C27—C28 | 1.538 (5) |
| C11—C12 | 1.385 (5) | C27—C29 | 1.544 (6) |
| C11—H11 | 0.9300 | C28—H28A | 0.9600 |
| C12—C13 | 1.407 (5) | C28—H28B | 0.9600 |
| C12—C15 | 1.543 (5) | C28—H28C | 0.9600 |
| C14—H14A | 0.9600 | C29—H29A | 0.9600 |
| C14—H14B | 0.9600 | C29—H29B | 0.9600 |
| C14—H14C | 0.9600 | C29—H29C | 0.9600 |
| C15—C16 | 1.528 (5) | C30—H30A | 0.9600 |
| C15—C17 | 1.530 (5) | C30—H30B | 0.9600 |
| C15—C18 | 1.533 (5) | C30—H30C | 0.9600 |
| C7—N1—C1 | 121.6 (3) | C15—C17—H17B | 109.5 |
| C19—N2—C6 | 120.5 (3) | H17A—C17—H17B | 109.5 |
| C13—O1—H1 | 109.5 | C15—C17—H17C | 109.5 |
| C25—O2—H2 | 109.5 | H17A—C17—H17C | 109.5 |
| C2—C1—C6 | 118.0 (3) | H17B—C17—H17C | 109.5 |
| C2—C1—N1 | 124.4 (3) | C15—C18—H18A | 109.5 |
| C6—C1—N1 | 117.6 (3) | C15—C18—H18B | 109.5 |
| C3—C2—C1 | 122.1 (4) | H18A—C18—H18B | 109.5 |
| C3—C2—H2A | 118.9 | C15—C18—H18C | 109.5 |
| C1—C2—H2A | 118.9 | H18A—C18—H18C | 109.5 |
| C2—C3—C4 | 119.7 (4) | H18B—C18—H18C | 109.5 |
| C2—C3—H3 | 120.1 | N2—C19—C20 | 123.7 (3) |
| C4—C3—H3 | 120.1 | N2—C19—H19 | 118.2 |
| C3—C4—C5 | 119.7 (4) | C20—C19—H19 | 118.2 |
| C3—C4—H4 | 120.1 | C21—C20—C25 | 119.3 (3) |
| C5—C4—H4 | 120.1 | C21—C20—C19 | 118.8 (3) |
| C4—C5—C6 | 121.2 (4) | C25—C20—C19 | 121.9 (3) |
| C4—C5—H5 | 119.4 | C22—C21—C20 | 121.6 (3) |
| C6—C5—H5 | 119.4 | C22—C21—H21 | 119.2 |
| C5—C6—C1 | 119.2 (3) | C20—C21—H21 | 119.2 |
| C5—C6—N2 | 121.4 (3) | C21—C22—C23 | 116.9 (3) |
| C1—C6—N2 | 119.4 (3) | C21—C22—C26 | 122.0 (4) |
| N1—C7—C8 | 124.0 (3) | C23—C22—C26 | 121.1 (3) |
| N1—C7—H7 | 118.0 | C24—C23—C22 | 124.6 (3) |
| C8—C7—H7 | 118.0 | C24—C23—H23 | 117.7 |
| C13—C8—C9 | 119.1 (3) | C22—C23—H23 | 117.7 |
| C13—C8—C7 | 121.5 (3) | C23—C24—C25 | 116.6 (3) |
| C9—C8—C7 | 119.3 (3) | C23—C24—C27 | 121.7 (3) |
| C10—C9—C8 | 122.1 (3) | C25—C24—C27 | 121.7 (3) |
| C10—C9—H9 | 119.0 | O2—C25—C24 | 119.5 (3) |
| C8—C9—H9 | 119.0 | O2—C25—C20 | 119.6 (3) |
| C9—C10—C11 | 116.8 (3) | C24—C25—C20 | 121.0 (3) |
| C9—C10—C14 | 122.4 (3) | C22—C26—H26A | 109.5 |
| C11—C10—C14 | 120.8 (3) | C22—C26—H26B | 109.5 |
| C12—C11—C10 | 124.6 (3) | H26A—C26—H26B | 109.5 |
| C12—C11—H11 | 117.7 | C22—C26—H26C | 109.5 |
| C10—C11—H11 | 117.7 | H26A—C26—H26C | 109.5 |
| C11—C12—C13 | 116.5 (3) | H26B—C26—H26C | 109.5 |
| C11—C12—C15 | 121.7 (3) | C30—C27—C24 | 112.7 (3) |
| C13—C12—C15 | 121.7 (3) | C30—C27—C28 | 106.6 (3) |
| O1—C13—C8 | 120.1 (3) | C24—C27—C28 | 110.9 (3) |
| O1—C13—C12 | 119.0 (3) | C30—C27—C29 | 107.8 (3) |
| C8—C13—C12 | 120.9 (3) | C24—C27—C29 | 108.7 (3) |
| C10—C14—H14A | 109.5 | C28—C27—C29 | 110.1 (4) |
| C10—C14—H14B | 109.5 | C27—C28—H28A | 109.5 |
| H14A—C14—H14B | 109.5 | C27—C28—H28B | 109.5 |
| C10—C14—H14C | 109.5 | H28A—C28—H28B | 109.5 |
| H14A—C14—H14C | 109.5 | C27—C28—H28C | 109.5 |
| H14B—C14—H14C | 109.5 | H28A—C28—H28C | 109.5 |
| C16—C15—C17 | 106.0 (3) | H28B—C28—H28C | 109.5 |
| C16—C15—C18 | 108.8 (3) | C27—C29—H29A | 109.5 |
| C17—C15—C18 | 110.1 (3) | C27—C29—H29B | 109.5 |
| C16—C15—C12 | 111.8 (3) | H29A—C29—H29B | 109.5 |
| C17—C15—C12 | 110.3 (3) | C27—C29—H29C | 109.5 |
| C18—C15—C12 | 109.7 (3) | H29A—C29—H29C | 109.5 |
| C15—C16—H16A | 109.5 | H29B—C29—H29C | 109.5 |
| C15—C16—H16B | 109.5 | C27—C30—H30A | 109.5 |
| H16A—C16—H16B | 109.5 | C27—C30—H30B | 109.5 |
| C15—C16—H16C | 109.5 | H30A—C30—H30B | 109.5 |
| H16A—C16—H16C | 109.5 | C27—C30—H30C | 109.5 |
| H16B—C16—H16C | 109.5 | H30A—C30—H30C | 109.5 |
| C15—C17—H17A | 109.5 | H30B—C30—H30C | 109.5 |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1···N1 | 0.82 | 1.89 | 2.605 (4) | 145. |
| O2—H2···N2 | 0.82 | 1.87 | 2.609 (4) | 149. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O1—H1···N1 | 0.82 | 1.89 | 2.605 (4) | 145. |
| O2—H2···N2 | 0.82 | 1.87 | 2.609 (4) | 149. |
This work was supported by the Foundation of Shandong Educational Committee (No. J10LB63) and the Key Project of Science and Technology of JNMC.
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Schiff base ligands attract much attention in pharmaceutical fields as well as in catalytic research. Here we report the molecular structure of a tetradentate Schiff base ligand, which is shown in Fig. 1.
The dihedral angles between the central benzene ring and the two benzene rings butylsalicylaldimine groups are 14.3 (2)° (C8-C13) and 40.6 (2)° (C20-C25). There are two strong intramolecular O—H···N hydrogen bonds which form S(6) rings (Bernstein et al., 1995). The hydrogen bonding in the title compound is different to that reported in the related structure (You et al., 2010) possibly owing to the steric effects of the bulky t-butyl substituents.