Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805041383/wn6397sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805041383/wn6397Isup2.hkl |
CCDC reference: 287024
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.004 Å
- Disorder in main residue
- R factor = 0.044
- wR factor = 0.082
- Data-to-parameter ratio = 14.8
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low .... 32 Perc. PLAT420_ALERT_2_B D-H Without Acceptor O3S - H3S ... ? PLAT601_ALERT_2_B Structure Contains Solvent Accessible VOIDS of . 117.00 A 3
Alert level C GOODF01_ALERT_2_C The least squares goodness of fit parameter lies outside the range 0.80 <> 2.00 Goodness of fit given = 0.616 PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.57 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C7 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C8 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C16 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C177 PLAT301_ALERT_3_C Main Residue Disorder ......................... 7.00 Perc. PLAT480_ALERT_4_C Long H...A H-Bond Reported H16I .. CG1 .. 2.91 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H16D .. CG2 .. 3.06 Ang. PLAT480_ALERT_4_C Long H...A H-Bond Reported H73A .. CG2 .. 2.95 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 3 PLAT737_ALERT_1_C D...A Calc 2.967(3), Rep 2.967(8) ...... 2.67 su-Rat C162 -O2 1.555 1.555 PLAT737_ALERT_1_C D...A Calc 3.033(4), Rep 3.033(9) ...... 2.25 su-Rat C82 -O1 1.555 1.555 PLAT737_ALERT_1_C D...A Calc 2.979(3), Rep 2.980(9) ...... 3.00 su-Rat C83 -O1 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 41.30 Deg. C171 -C17 -C178 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 39.40 Deg. C174 -C17 -C173 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 38.40 Deg. C179 -C17 -C173 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 44.80 Deg. C172 -C17 -C175 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 28.00 Deg. C178 -C17 -C175 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 38.70 Deg. C179 -C17 -C176 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 34.60 Deg. C172 -C17 -C176 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 34.80 Deg. C174 -C17 -C177 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 38.90 Deg. C171 -C17 -C177 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 24 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 17 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion
The title compound was synthesized by the reaction of 3,5-di-tert-butylsalicylaldehyde and 6-methyl-2-aminopyridine, under a nitrogen atmosphere. A mixture of 3,5-di-tertbutylsalicylaldehyde (4 mmol) and 2-amino-6-methylpyridine (4.4 mmol) in ethanol (20 ml) was heated under reflux for 24 h, after adding formic acid as a catalyst. It was then allowed to stand at room temperature overnight. The solid product was isolated by filtration, and purified by thin-layer chromatography. Pale-yellow single crystals suitable for X-ray diffraction were obtained by evaporation of a methanol solution of the product.
After their location, all H atoms were placed in idealized positions and refined using a riding model; C—H = 0.93–0.98 Å, O—H = 0.82 Å and Uiso(H) = 1.2Ueq(C) or 1.5Ueq(O). One of the tert-butyl groups is disordered over three sites; there are three sets of methyl groups (C171/C172/C173, C174/C175/C176 and C177/C178/C179) with site-occupancy factors of 1/2 0.25 and 0.25 for groups 1, 2 and 3, respectively.
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.
C36H48N2O2·CH4O | Z = 2 |
Mr = 572.81 | F(000) = 624 |
Triclinic, P1 | Dx = 1.091 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.282 (2) Å | Cell parameters from 877 reflections |
b = 12.775 (3) Å | θ = 2.3–18.5° |
c = 15.601 (3) Å | µ = 0.07 mm−1 |
α = 66.313 (4)° | T = 273 K |
β = 82.711 (4)° | Block, pale yellow |
γ = 68.295 (4)° | 0.30 × 0.20 × 0.15 mm |
V = 1743.0 (7) Å3 |
Bruker SMART CCD area-detector diffractometer | 1913 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.049 |
Graphite monochromator | θmax = 25.0°, θmin = 2.1° |
ϕ and ω scans | h = −12→12 |
9105 measured reflections | k = −15→13 |
6047 independent reflections | l = −18→10 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.082 | H-atom parameters constrained |
S = 0.62 | w = 1/[σ2(Fo2) + (0.0568P)2] where P = (Fo2 + 2Fc2)/3 |
6047 reflections | (Δ/σ)max = 0.015 |
408 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.32 e Å−3 |
C36H48N2O2·CH4O | γ = 68.295 (4)° |
Mr = 572.81 | V = 1743.0 (7) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.282 (2) Å | Mo Kα radiation |
b = 12.775 (3) Å | µ = 0.07 mm−1 |
c = 15.601 (3) Å | T = 273 K |
α = 66.313 (4)° | 0.30 × 0.20 × 0.15 mm |
β = 82.711 (4)° |
Bruker SMART CCD area-detector diffractometer | 1913 reflections with I > 2σ(I) |
9105 measured reflections | Rint = 0.049 |
6047 independent reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.082 | H-atom parameters constrained |
S = 0.62 | Δρmax = 0.27 e Å−3 |
6047 reflections | Δρmin = −0.32 e Å−3 |
408 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. |
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 | Occ. (<1) | |
C1 | 0.6021 (3) | −0.1768 (2) | 0.42805 (17) | 0.0470 (8) | |
H1 | 0.6285 | −0.2396 | 0.4866 | 0.056* | |
C2 | 0.7072 (3) | −0.1602 (2) | 0.36449 (18) | 0.0403 (7) | |
C3 | 0.6611 (3) | −0.0647 (2) | 0.27628 (18) | 0.0378 (7) | |
C4 | 0.5223 (3) | 0.0071 (2) | 0.25645 (17) | 0.0349 (7) | |
C5 | 0.4230 (3) | −0.0129 (2) | 0.32417 (18) | 0.0399 (7) | |
H5 | 0.3297 | 0.0378 | 0.3107 | 0.048* | |
C6 | 0.4599 (3) | −0.1068 (3) | 0.41119 (18) | 0.0416 (8) | |
C7 | 0.3553 (3) | −0.1365 (3) | 0.48789 (19) | 0.0511 (8) | |
C71 | 0.2052 (3) | −0.0515 (3) | 0.45589 (17) | 0.0764 (10) | |
H71A | 0.1822 | −0.0569 | 0.4004 | 0.115* | |
H71B | 0.1968 | 0.0309 | 0.4426 | 0.115* | |
H71C | 0.1423 | −0.0752 | 0.5045 | 0.115* | |
C72 | 0.3638 (3) | −0.2678 (3) | 0.51308 (19) | 0.0886 (11) | |
H72A | 0.3481 | −0.2772 | 0.4577 | 0.133* | |
H72B | 0.2938 | −0.2852 | 0.5578 | 0.133* | |
H72C | 0.4549 | −0.3233 | 0.5395 | 0.133* | |
C73 | 0.3894 (3) | −0.1228 (3) | 0.57513 (18) | 0.0717 (10) | |
H73A | 0.3275 | −0.1473 | 0.6243 | 0.107* | |
H73B | 0.3775 | −0.0392 | 0.5601 | 0.107* | |
H73C | 0.4845 | −0.1735 | 0.5955 | 0.107* | |
C8 | 0.8613 (3) | −0.2395 (3) | 0.38920 (19) | 0.0523 (8) | |
C81 | 0.8822 (3) | −0.3311 (2) | 0.49233 (17) | 0.0823 (11) | |
H81A | 0.8499 | −0.2872 | 0.5330 | 0.123* | |
H81B | 0.9798 | −0.3794 | 0.5052 | 0.123* | |
H81C | 0.8298 | −0.3835 | 0.5028 | 0.123* | |
C82 | 0.9172 (3) | −0.3130 (3) | 0.32641 (19) | 0.0804 (10) | |
H82A | 0.8649 | −0.3654 | 0.3365 | 0.121* | |
H82B | 1.0143 | −0.3616 | 0.3416 | 0.121* | |
H82C | 0.9072 | −0.2579 | 0.2619 | 0.121* | |
C83 | 0.9485 (3) | −0.1596 (3) | 0.37694 (18) | 0.0757 (10) | |
H83A | 0.9440 | −0.1053 | 0.3125 | 0.114* | |
H83B | 1.0442 | −0.2107 | 0.3953 | 0.114* | |
H83C | 0.9120 | −0.1128 | 0.4153 | 0.114* | |
C9 | 0.4726 (3) | 0.1021 (2) | 0.15918 (17) | 0.0385 (7) | |
H9 | 0.3888 | 0.0946 | 0.1423 | 0.046* | |
C10 | 0.5529 (3) | 0.2521 (2) | 0.16194 (16) | 0.0344 (7) | |
C11 | 0.6870 (3) | 0.1748 (2) | 0.15559 (16) | 0.0362 (7) | |
C12 | 0.8015 (3) | 0.2019 (2) | 0.16614 (16) | 0.0415 (7) | |
H12 | 0.8912 | 0.1499 | 0.1617 | 0.050* | |
C13 | 0.7854 (3) | 0.3039 (3) | 0.18296 (17) | 0.0409 (7) | |
C14 | 0.6481 (3) | 0.3817 (2) | 0.18559 (15) | 0.0444 (8) | |
H14 | 0.6356 | 0.4523 | 0.1949 | 0.053* | |
C15 | 0.5292 (3) | 0.3597 (2) | 0.17504 (16) | 0.0360 (7) | |
C16 | 0.3817 (3) | 0.4517 (2) | 0.17389 (19) | 0.0453 (8) | |
C161 | 0.2981 (2) | 0.3937 (2) | 0.25637 (17) | 0.0644 (9) | |
H16A | 0.2955 | 0.3208 | 0.2536 | 0.097* | |
H16B | 0.2044 | 0.4504 | 0.2527 | 0.097* | |
H16C | 0.3424 | 0.3737 | 0.3143 | 0.097* | |
C162 | 0.3047 (3) | 0.4945 (2) | 0.08056 (17) | 0.0698 (10) | |
H16D | 0.3534 | 0.5364 | 0.0298 | 0.105* | |
H16E | 0.2109 | 0.5488 | 0.0817 | 0.105* | |
H16F | 0.3018 | 0.4250 | 0.0721 | 0.105* | |
C163 | 0.3846 (3) | 0.5655 (2) | 0.1843 (2) | 0.0855 (11) | |
H16G | 0.4339 | 0.5413 | 0.2413 | 0.128* | |
H16H | 0.2905 | 0.6188 | 0.1859 | 0.128* | |
H16I | 0.4313 | 0.6075 | 0.1320 | 0.128* | |
C17 | 0.9119 (3) | 0.3345 (3) | 0.19624 (19) | 0.0470 (8) | |
C171 | 1.0533 (6) | 0.2400 (6) | 0.1900 (6) | 0.068 (2)* | 0.50 |
H31 | 1.0582 | 0.2320 | 0.1310 | 0.101* | 0.50 |
H32 | 1.0630 | 0.1627 | 0.2400 | 0.101* | 0.50 |
H33 | 1.1274 | 0.2661 | 0.1951 | 0.101* | 0.50 |
C172 | 0.9082 (7) | 0.3419 (9) | 0.2909 (4) | 0.065 (2)* | 0.50 |
H34 | 0.9884 | 0.3589 | 0.2988 | 0.097* | 0.50 |
H35 | 0.9096 | 0.2656 | 0.3392 | 0.097* | 0.50 |
H36 | 0.8243 | 0.4060 | 0.2948 | 0.097* | 0.50 |
C173 | 0.9023 (7) | 0.4610 (6) | 0.1177 (5) | 0.058 (2)* | 0.50 |
H37 | 0.9800 | 0.4818 | 0.1246 | 0.088* | 0.50 |
H38 | 0.8163 | 0.5223 | 0.1228 | 0.088* | 0.50 |
H39 | 0.9048 | 0.4566 | 0.0575 | 0.088* | 0.50 |
C174 | 0.9702 (16) | 0.3859 (17) | 0.1071 (8) | 0.064 (4)* | 0.25 |
H41 | 0.9027 | 0.4628 | 0.0700 | 0.096* | 0.25 |
H42 | 0.9936 | 0.3311 | 0.0752 | 0.096* | 0.25 |
H43 | 1.0530 | 0.3981 | 0.1166 | 0.096* | 0.25 |
C175 | 0.9783 (15) | 0.2427 (15) | 0.2961 (8) | 0.058 (4)* | 0.25 |
H44 | 1.0083 | 0.1606 | 0.2993 | 0.086* | 0.25 |
H45 | 0.9099 | 0.2526 | 0.3429 | 0.086* | 0.25 |
H46 | 1.0574 | 0.2589 | 0.3072 | 0.086* | 0.25 |
C176 | 0.8663 (12) | 0.4237 (13) | 0.2521 (11) | 0.053 (4)* | 0.25 |
H47 | 0.9463 | 0.4393 | 0.2622 | 0.080* | 0.25 |
H48 | 0.8292 | 0.3858 | 0.3114 | 0.080* | 0.25 |
H49 | 0.7959 | 0.4993 | 0.2162 | 0.080* | 0.25 |
C177 | 1.0289 (11) | 0.3055 (13) | 0.1212 (8) | 0.036 (3)* | 0.25 |
H61 | 0.9892 | 0.3532 | 0.0590 | 0.054* | 0.25 |
H62 | 1.0596 | 0.2203 | 0.1324 | 0.054* | 0.25 |
H63 | 1.1072 | 0.3257 | 0.1277 | 0.054* | 0.25 |
C178 | 1.0206 (15) | 0.2143 (11) | 0.2624 (12) | 0.062 (5)* | 0.25 |
H64 | 1.0601 | 0.1593 | 0.2307 | 0.093* | 0.25 |
H65 | 0.9750 | 0.1771 | 0.3177 | 0.093* | 0.25 |
H66 | 1.0937 | 0.2324 | 0.2797 | 0.093* | 0.25 |
C179 | 0.8759 (11) | 0.4668 (10) | 0.1807 (12) | 0.050 (4)* | 0.25 |
H67 | 0.9597 | 0.4810 | 0.1852 | 0.075* | 0.25 |
H68 | 0.8120 | 0.4855 | 0.2274 | 0.075* | 0.25 |
H69 | 0.8331 | 0.5181 | 0.1197 | 0.075* | 0.25 |
C18 | 0.7097 (3) | 0.0671 (2) | 0.12950 (17) | 0.0388 (7) | |
H18 | 0.7789 | 0.0674 | 0.0801 | 0.047* | |
C19 | 0.5500 (3) | 0.1264 (2) | −0.0019 (2) | 0.0404 (7) | |
C20 | 0.4137 (3) | 0.1884 (2) | −0.03731 (19) | 0.0535 (9) | |
H20 | 0.3390 | 0.2046 | 0.0015 | 0.064* | |
C21 | 0.3925 (3) | 0.2253 (2) | −0.1323 (2) | 0.0616 (9) | |
H21 | 0.3021 | 0.2641 | −0.1580 | 0.074* | |
C22 | 0.5046 (4) | 0.2046 (3) | −0.1886 (2) | 0.0597 (9) | |
H22 | 0.4913 | 0.2295 | −0.2526 | 0.072* | |
C23 | 0.6366 (3) | 0.1469 (3) | −0.1490 (2) | 0.0537 (9) | |
C24 | 0.7648 (3) | 0.1250 (3) | −0.20795 (18) | 0.0815 (11) | |
H24A | 0.8330 | 0.1480 | −0.1902 | 0.122* | |
H24B | 0.7389 | 0.1731 | −0.2729 | 0.122* | |
H24C | 0.8039 | 0.0401 | −0.1982 | 0.122* | |
N1 | 0.5799 (2) | 0.07651 (18) | 0.09459 (15) | 0.0387 (6) | |
N2 | 0.6617 (2) | 0.10429 (19) | −0.05550 (17) | 0.0477 (6) | |
O1 | 0.76077 (16) | −0.04700 (15) | 0.20879 (11) | 0.0432 (5) | |
O2 | 0.43683 (16) | 0.22460 (15) | 0.15522 (10) | 0.0395 (5) | |
C3S | 0.9833 (4) | 0.8192 (3) | 0.0525 (2) | 0.1289 (17) | |
H3S1 | 1.0050 | 0.8584 | 0.0871 | 0.193* | |
H3S2 | 1.0685 | 0.7644 | 0.0388 | 0.193* | |
H3S3 | 0.9249 | 0.7742 | 0.0890 | 0.193* | |
O3S | 0.9177 (3) | 0.9016 (3) | −0.0256 (2) | 0.2240 (19) | |
H3S | 0.8631 | 0.8780 | −0.0403 | 0.336* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.052 (2) | 0.044 (2) | 0.0390 (19) | −0.0188 (18) | −0.0012 (16) | −0.0080 (15) |
C2 | 0.0380 (19) | 0.036 (2) | 0.0437 (19) | −0.0104 (16) | −0.0015 (15) | −0.0138 (15) |
C3 | 0.0384 (19) | 0.038 (2) | 0.0431 (19) | −0.0186 (16) | 0.0120 (16) | −0.0197 (16) |
C4 | 0.0336 (18) | 0.0356 (19) | 0.0392 (18) | −0.0142 (16) | 0.0025 (15) | −0.0166 (15) |
C5 | 0.0369 (18) | 0.040 (2) | 0.0473 (19) | −0.0143 (15) | −0.0003 (16) | −0.0195 (16) |
C6 | 0.045 (2) | 0.044 (2) | 0.0408 (19) | −0.0216 (17) | 0.0015 (16) | −0.0163 (15) |
C7 | 0.048 (2) | 0.064 (2) | 0.043 (2) | −0.0282 (19) | 0.0126 (16) | −0.0183 (17) |
C71 | 0.051 (2) | 0.104 (3) | 0.061 (2) | −0.031 (2) | 0.0135 (17) | −0.0198 (19) |
C72 | 0.107 (3) | 0.081 (3) | 0.094 (3) | −0.063 (2) | 0.041 (2) | −0.033 (2) |
C73 | 0.075 (2) | 0.090 (3) | 0.049 (2) | −0.032 (2) | 0.0113 (17) | −0.0261 (19) |
C8 | 0.041 (2) | 0.052 (2) | 0.046 (2) | −0.0028 (18) | −0.0037 (15) | −0.0125 (17) |
C81 | 0.059 (2) | 0.075 (3) | 0.067 (2) | 0.000 (2) | −0.0101 (17) | 0.0000 (19) |
C82 | 0.075 (2) | 0.064 (3) | 0.079 (3) | 0.004 (2) | 0.0004 (19) | −0.031 (2) |
C83 | 0.048 (2) | 0.095 (3) | 0.082 (2) | −0.026 (2) | −0.0049 (17) | −0.030 (2) |
C9 | 0.0380 (19) | 0.042 (2) | 0.0435 (19) | −0.0207 (16) | 0.0044 (15) | −0.0187 (16) |
C10 | 0.0303 (18) | 0.037 (2) | 0.0372 (18) | −0.0182 (16) | −0.0001 (13) | −0.0090 (14) |
C11 | 0.0320 (18) | 0.0342 (19) | 0.0388 (18) | −0.0117 (16) | 0.0040 (14) | −0.0114 (14) |
C12 | 0.0354 (18) | 0.043 (2) | 0.0413 (18) | −0.0150 (16) | −0.0010 (13) | −0.0104 (15) |
C13 | 0.040 (2) | 0.045 (2) | 0.0410 (18) | −0.0232 (18) | 0.0025 (14) | −0.0127 (15) |
C14 | 0.0456 (19) | 0.038 (2) | 0.0529 (19) | −0.0179 (17) | 0.0020 (15) | −0.0174 (15) |
C15 | 0.0353 (19) | 0.035 (2) | 0.0383 (18) | −0.0144 (16) | 0.0019 (14) | −0.0126 (14) |
C16 | 0.0336 (18) | 0.036 (2) | 0.068 (2) | −0.0093 (16) | 0.0015 (16) | −0.0240 (16) |
C161 | 0.0451 (19) | 0.077 (3) | 0.076 (2) | −0.0208 (18) | 0.0150 (17) | −0.0390 (18) |
C162 | 0.058 (2) | 0.057 (2) | 0.073 (2) | −0.0055 (18) | −0.0156 (17) | −0.0121 (18) |
C163 | 0.056 (2) | 0.057 (3) | 0.151 (3) | −0.0105 (19) | 0.000 (2) | −0.055 (2) |
C17 | 0.0386 (19) | 0.049 (2) | 0.052 (2) | −0.0182 (18) | −0.0018 (15) | −0.0144 (17) |
C18 | 0.0390 (19) | 0.042 (2) | 0.0347 (18) | −0.0185 (16) | 0.0064 (14) | −0.0126 (15) |
C19 | 0.050 (2) | 0.0311 (19) | 0.044 (2) | −0.0186 (16) | 0.0024 (18) | −0.0149 (15) |
C20 | 0.056 (2) | 0.059 (2) | 0.044 (2) | −0.0205 (18) | −0.0025 (16) | −0.0164 (16) |
C21 | 0.070 (2) | 0.061 (2) | 0.053 (2) | −0.029 (2) | −0.010 (2) | −0.0132 (19) |
C22 | 0.084 (3) | 0.062 (2) | 0.044 (2) | −0.038 (2) | −0.001 (2) | −0.0202 (18) |
C23 | 0.074 (3) | 0.053 (2) | 0.049 (2) | −0.035 (2) | 0.012 (2) | −0.0260 (18) |
C24 | 0.096 (3) | 0.103 (3) | 0.061 (2) | −0.046 (2) | 0.031 (2) | −0.044 (2) |
N1 | 0.0372 (15) | 0.0437 (16) | 0.0358 (16) | −0.0164 (13) | 0.0015 (12) | −0.0141 (12) |
N2 | 0.0599 (18) | 0.0496 (17) | 0.0429 (17) | −0.0266 (14) | 0.0114 (14) | −0.0231 (13) |
O1 | 0.0388 (12) | 0.0395 (13) | 0.0443 (12) | −0.0107 (10) | 0.0035 (10) | −0.0128 (10) |
O2 | 0.0348 (11) | 0.0359 (13) | 0.0513 (12) | −0.0144 (10) | 0.0022 (9) | −0.0187 (9) |
C3S | 0.143 (4) | 0.097 (4) | 0.075 (3) | 0.014 (3) | 0.000 (3) | −0.014 (2) |
O3S | 0.208 (4) | 0.216 (4) | 0.126 (3) | 0.071 (3) | −0.008 (2) | −0.074 (2) |
C1—C2 | 1.388 (3) | C163—H16H | 0.9600 |
C1—C6 | 1.396 (3) | C163—H16I | 0.9600 |
C1—H1 | 0.9300 | C17—C174 | 1.439 (11) |
C2—C3 | 1.412 (3) | C17—C179 | 1.511 (11) |
C2—C8 | 1.529 (3) | C17—C172 | 1.512 (6) |
C3—C4 | 1.375 (3) | C17—C171 | 1.530 (6) |
C3—O1 | 1.384 (2) | C17—C178 | 1.557 (13) |
C4—C5 | 1.389 (3) | C17—C173 | 1.563 (6) |
C4—C9 | 1.515 (3) | C17—C175 | 1.575 (12) |
C5—C6 | 1.382 (3) | C17—C176 | 1.605 (12) |
C5—H5 | 0.9300 | C17—C177 | 1.617 (10) |
C6—C7 | 1.531 (3) | C171—H31 | 0.9600 |
C7—C71 | 1.527 (3) | C171—H32 | 0.9600 |
C7—C72 | 1.532 (3) | C171—H33 | 0.9600 |
C7—C73 | 1.537 (3) | C172—H34 | 0.9601 |
C71—H71A | 0.9600 | C172—H35 | 0.9601 |
C71—H71B | 0.9600 | C172—H36 | 0.9601 |
C71—H71C | 0.9600 | C173—H37 | 0.9600 |
C72—H72A | 0.9600 | C173—H38 | 0.9600 |
C72—H72B | 0.9600 | C173—H39 | 0.9600 |
C72—H72C | 0.9600 | C174—H41 | 0.9602 |
C73—H73A | 0.9600 | C174—H42 | 0.9602 |
C73—H73B | 0.9600 | C174—H43 | 0.9602 |
C73—H73C | 0.9600 | C175—H44 | 0.9602 |
C8—C83 | 1.536 (3) | C175—H45 | 0.9602 |
C8—C82 | 1.540 (3) | C175—H46 | 0.9602 |
C8—C81 | 1.547 (3) | C176—H47 | 0.9602 |
C81—H81A | 0.9600 | C176—H48 | 0.9602 |
C81—H81B | 0.9600 | C176—H49 | 0.9602 |
C81—H81C | 0.9600 | C177—H61 | 0.9601 |
C82—H82A | 0.9600 | C177—H62 | 0.9601 |
C82—H82B | 0.9600 | C177—H63 | 0.9601 |
C82—H82C | 0.9600 | C178—H64 | 0.9601 |
C83—H83A | 0.9600 | C178—H65 | 0.9601 |
C83—H83B | 0.9600 | C178—H66 | 0.9601 |
C83—H83C | 0.9600 | C179—H67 | 0.9602 |
C9—N1 | 1.434 (3) | C179—H68 | 0.9602 |
C9—O2 | 1.445 (3) | C179—H69 | 0.9602 |
C9—H9 | 0.9800 | C18—O1 | 1.442 (2) |
C10—C11 | 1.387 (3) | C18—N1 | 1.451 (3) |
C10—O2 | 1.390 (2) | C18—H18 | 0.9800 |
C10—C15 | 1.398 (3) | C19—N2 | 1.344 (3) |
C11—C12 | 1.389 (3) | C19—C20 | 1.386 (3) |
C11—C18 | 1.517 (3) | C19—N1 | 1.402 (3) |
C12—C13 | 1.377 (3) | C20—C21 | 1.383 (3) |
C12—H12 | 0.9300 | C20—H20 | 0.9300 |
C13—C14 | 1.401 (3) | C21—C22 | 1.368 (3) |
C13—C17 | 1.549 (3) | C21—H21 | 0.9300 |
C14—C15 | 1.394 (3) | C22—C23 | 1.369 (3) |
C14—H14 | 0.9300 | C22—H22 | 0.9300 |
C15—C16 | 1.535 (3) | C23—N2 | 1.359 (3) |
C16—C163 | 1.538 (3) | C23—C24 | 1.512 (3) |
C16—C161 | 1.538 (3) | C24—H24A | 0.9600 |
C16—C162 | 1.542 (3) | C24—H24B | 0.9600 |
C161—H16A | 0.9600 | C24—H24C | 0.9600 |
C161—H16B | 0.9600 | C3S—O3S | 1.304 (3) |
C161—H16C | 0.9600 | C3S—H3S1 | 0.9600 |
C162—H16D | 0.9600 | C3S—H3S2 | 0.9600 |
C162—H16E | 0.9600 | C3S—H3S3 | 0.9600 |
C162—H16F | 0.9600 | O3S—H3S | 0.8200 |
C163—H16G | 0.9600 | ||
C2—C1—C6 | 125.3 (2) | C179—C17—C171 | 129.5 (5) |
C2—C1—H1 | 117.4 | C172—C17—C171 | 107.4 (4) |
C6—C1—H1 | 117.4 | C174—C17—C13 | 110.3 (5) |
C1—C2—C3 | 115.0 (2) | C179—C17—C13 | 113.7 (4) |
C1—C2—C8 | 122.0 (2) | C172—C17—C13 | 110.4 (3) |
C3—C2—C8 | 123.0 (2) | C171—C17—C13 | 113.2 (3) |
C4—C3—O1 | 120.5 (2) | C174—C17—C178 | 111.8 (7) |
C4—C3—C2 | 121.9 (2) | C179—C17—C178 | 132.3 (7) |
O1—C3—C2 | 117.6 (2) | C172—C17—C178 | 71.9 (6) |
C3—C4—C5 | 120.0 (2) | C171—C17—C178 | 41.3 (5) |
C3—C4—C9 | 121.3 (2) | C13—C17—C178 | 107.4 (5) |
C5—C4—C9 | 118.5 (2) | C174—C17—C173 | 39.4 (6) |
C6—C5—C4 | 121.3 (2) | C179—C17—C173 | 38.4 (5) |
C6—C5—H5 | 119.4 | C172—C17—C173 | 109.3 (4) |
C4—C5—H5 | 119.4 | C171—C17—C173 | 108.4 (4) |
C5—C6—C1 | 116.5 (3) | C13—C17—C173 | 108.1 (3) |
C5—C6—C7 | 124.0 (3) | C178—C17—C173 | 141.1 (6) |
C1—C6—C7 | 119.5 (2) | C174—C17—C175 | 133.5 (7) |
C71—C7—C6 | 111.8 (2) | C179—C17—C175 | 113.5 (7) |
C71—C7—C72 | 108.3 (2) | C172—C17—C175 | 44.8 (5) |
C6—C7—C72 | 108.9 (2) | C171—C17—C175 | 68.3 (6) |
C71—C7—C73 | 107.9 (2) | C13—C17—C175 | 106.9 (5) |
C6—C7—C73 | 110.2 (2) | C178—C17—C175 | 28.0 (6) |
C72—C7—C73 | 109.7 (2) | C173—C17—C175 | 142.7 (6) |
C7—C71—H71A | 109.5 | C174—C17—C176 | 112.0 (7) |
C7—C71—H71B | 109.5 | C179—C17—C176 | 38.7 (5) |
H71A—C71—H71B | 109.5 | C172—C17—C176 | 34.6 (4) |
C7—C71—H71C | 109.5 | C171—C17—C176 | 131.3 (5) |
H71A—C71—H71C | 109.5 | C13—C17—C176 | 110.2 (4) |
H71B—C71—H71C | 109.5 | C178—C17—C176 | 104.8 (7) |
C7—C72—H72A | 109.5 | C173—C17—C176 | 77.0 (5) |
C7—C72—H72B | 109.5 | C175—C17—C176 | 79.1 (7) |
H72A—C72—H72B | 109.5 | C174—C17—C177 | 34.8 (6) |
C7—C72—H72C | 109.5 | C179—C17—C177 | 107.3 (6) |
H72A—C72—H72C | 109.5 | C172—C17—C177 | 137.3 (5) |
H72B—C72—H72C | 109.5 | C171—C17—C177 | 38.9 (4) |
C7—C73—H73A | 109.5 | C13—C17—C177 | 108.5 (4) |
C7—C73—H73B | 109.5 | C178—C17—C177 | 80.2 (6) |
H73A—C73—H73B | 109.5 | C173—C17—C177 | 74.0 (5) |
C7—C73—H73C | 109.5 | C175—C17—C177 | 106.6 (7) |
H73A—C73—H73C | 109.5 | C176—C17—C177 | 137.1 (6) |
H73B—C73—H73C | 109.5 | C17—C171—H31 | 109.5 |
C2—C8—C83 | 110.3 (2) | C17—C171—H32 | 109.4 |
C2—C8—C82 | 109.9 (2) | C17—C171—H33 | 109.5 |
C83—C8—C82 | 109.9 (2) | C17—C172—H34 | 109.5 |
C2—C8—C81 | 111.8 (2) | C17—C172—H35 | 109.5 |
C83—C8—C81 | 106.9 (2) | C17—C172—H36 | 109.4 |
C82—C8—C81 | 107.9 (3) | C17—C173—H37 | 109.5 |
C8—C81—H81A | 109.5 | C17—C173—H38 | 109.5 |
C8—C81—H81B | 109.5 | C17—C173—H39 | 109.4 |
H81A—C81—H81B | 109.5 | C17—C174—H41 | 109.6 |
C8—C81—H81C | 109.5 | C17—C174—H42 | 109.4 |
H81A—C81—H81C | 109.5 | H41—C174—H42 | 109.5 |
H81B—C81—H81C | 109.5 | C17—C174—H43 | 109.5 |
C8—C82—H82A | 109.5 | H41—C174—H43 | 109.5 |
C8—C82—H82B | 109.5 | H42—C174—H43 | 109.4 |
H82A—C82—H82B | 109.5 | C17—C175—H44 | 109.6 |
C8—C82—H82C | 109.5 | C17—C175—H45 | 109.4 |
H82A—C82—H82C | 109.5 | H44—C175—H45 | 109.5 |
H82B—C82—H82C | 109.5 | C17—C175—H46 | 109.4 |
C8—C83—H83A | 109.5 | H44—C175—H46 | 109.5 |
C8—C83—H83B | 109.5 | H45—C175—H46 | 109.5 |
H83A—C83—H83B | 109.5 | C17—C176—H47 | 109.4 |
C8—C83—H83C | 109.5 | C17—C176—H48 | 109.6 |
H83A—C83—H83C | 109.5 | H47—C176—H48 | 109.5 |
H83B—C83—H83C | 109.5 | C17—C176—H49 | 109.4 |
N1—C9—O2 | 111.51 (19) | H47—C176—H49 | 109.5 |
N1—C9—C4 | 108.4 (2) | H48—C176—H49 | 109.5 |
O2—C9—C4 | 111.7 (2) | C17—C177—H61 | 109.5 |
N1—C9—H9 | 108.4 | C17—C177—H62 | 109.4 |
O2—C9—H9 | 108.4 | C17—C177—H63 | 109.5 |
C4—C9—H9 | 108.4 | C17—C178—H64 | 109.5 |
C11—C10—O2 | 120.5 (2) | C17—C178—H65 | 109.4 |
C11—C10—C15 | 121.8 (2) | C17—C178—H66 | 109.6 |
O2—C10—C15 | 117.7 (2) | C17—C179—H67 | 109.5 |
C10—C11—C12 | 119.4 (3) | C17—C179—H68 | 109.6 |
C10—C11—C18 | 120.8 (2) | C17—C179—H69 | 109.4 |
C12—C11—C18 | 119.6 (2) | O1—C18—N1 | 108.79 (19) |
C13—C12—C11 | 121.6 (3) | O1—C18—C11 | 111.3 (2) |
C13—C12—H12 | 119.2 | N1—C18—C11 | 110.4 (2) |
C11—C12—H12 | 119.2 | O1—C18—H18 | 108.8 |
C12—C13—C14 | 117.0 (2) | N1—C18—H18 | 108.8 |
C12—C13—C17 | 122.3 (3) | C11—C18—H18 | 108.8 |
C14—C13—C17 | 120.6 (3) | N2—C19—C20 | 123.3 (3) |
C15—C14—C13 | 123.9 (3) | N2—C19—N1 | 115.1 (3) |
C15—C14—H14 | 118.0 | C20—C19—N1 | 121.6 (3) |
C13—C14—H14 | 118.1 | C21—C20—C19 | 117.8 (3) |
C14—C15—C10 | 116.1 (2) | C21—C20—H20 | 121.1 |
C14—C15—C16 | 121.3 (3) | C19—C20—H20 | 121.1 |
C10—C15—C16 | 122.5 (2) | C22—C21—C20 | 120.0 (3) |
C15—C16—C163 | 112.2 (2) | C22—C21—H21 | 120.0 |
C15—C16—C161 | 110.3 (2) | C20—C21—H21 | 120.0 |
C163—C16—C161 | 106.6 (2) | C21—C22—C23 | 118.9 (3) |
C15—C16—C162 | 110.0 (2) | C21—C22—H22 | 120.6 |
C163—C16—C162 | 107.7 (2) | C23—C22—H22 | 120.6 |
C161—C16—C162 | 110.0 (2) | N2—C23—C22 | 123.0 (3) |
C16—C161—H16A | 109.5 | N2—C23—C24 | 115.7 (3) |
C16—C161—H16B | 109.5 | C22—C23—C24 | 121.3 (3) |
H16A—C161—H16B | 109.5 | C23—C24—H24A | 109.5 |
C16—C161—H16C | 109.5 | C23—C24—H24B | 109.5 |
H16A—C161—H16C | 109.5 | H24A—C24—H24B | 109.5 |
H16B—C161—H16C | 109.5 | C23—C24—H24C | 109.5 |
C16—C162—H16D | 109.5 | H24A—C24—H24C | 109.5 |
C16—C162—H16E | 109.5 | H24B—C24—H24C | 109.5 |
H16D—C162—H16E | 109.5 | C19—N1—C9 | 120.9 (2) |
C16—C162—H16F | 109.5 | C19—N1—C18 | 120.8 (2) |
H16D—C162—H16F | 109.5 | C9—N1—C18 | 107.8 (2) |
H16E—C162—H16F | 109.5 | C19—N2—C23 | 116.9 (3) |
C16—C163—H16G | 109.5 | C3—O1—C18 | 113.10 (19) |
C16—C163—H16H | 109.5 | C10—O2—C9 | 113.16 (19) |
H16G—C163—H16H | 109.5 | O3S—C3S—H3S1 | 109.5 |
C16—C163—H16I | 109.5 | O3S—C3S—H3S2 | 109.5 |
H16G—C163—H16I | 109.5 | H3S1—C3S—H3S2 | 109.5 |
H16H—C163—H16I | 109.5 | O3S—C3S—H3S3 | 109.5 |
C174—C17—C179 | 75.4 (7) | H3S1—C3S—H3S3 | 109.5 |
C174—C17—C172 | 135.4 (6) | H3S2—C3S—H3S3 | 109.5 |
C179—C17—C172 | 72.0 (6) | C3S—O3S—H3S | 109.5 |
C174—C17—C171 | 71.9 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
C18—H18···N2 | 0.98 | 2.36 | 2.808 (3) | 107 |
C161—H16A···O2 | 0.96 | 2.37 | 3.013 (6) | 124 |
C162—H16F···O2 | 0.96 | 2.31 | 2.967 (8) | 125 |
C82—H82C···O1 | 0.96 | 2.40 | 3.033 (9) | 124 |
C83—H83A···O1 | 0.96 | 2.34 | 2.980 (9) | 123 |
C163—H16I···Cg1i | 0.96 | 2.91 | 3.565 (7) | 127 |
C162—H16D···Cg2ii | 0.96 | 3.06 | 3.893 (11) | 146 |
C73—H73A···Cg2iii | 0.96 | 2.95 | 3.725 (9) | 138 |
C24—H24B···Cg1i | 0.96 | 2.65 | 3.147 (7) | 113 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x−1, y+1, z−1; (iii) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C36H48N2O2·CH4O |
Mr | 572.81 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 273 |
a, b, c (Å) | 10.282 (2), 12.775 (3), 15.601 (3) |
α, β, γ (°) | 66.313 (4), 82.711 (4), 68.295 (4) |
V (Å3) | 1743.0 (7) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.30 × 0.20 × 0.15 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9105, 6047, 1913 |
Rint | 0.049 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.082, 0.62 |
No. of reflections | 6047 |
No. of parameters | 408 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.27, −0.32 |
Computer programs: SMART (Bruker, 1997), SMART, SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
C18—H18···N2 | 0.98 | 2.36 | 2.808 (3) | 107 |
C161—H16A···O2 | 0.96 | 2.37 | 3.013 (6) | 124 |
C162—H16F···O2 | 0.96 | 2.31 | 2.967 (8) | 125 |
C82—H82C···O1 | 0.96 | 2.40 | 3.033 (9) | 124 |
C83—H83A···O1 | 0.96 | 2.34 | 2.980 (9) | 123 |
C163—H16I···Cg1i | 0.96 | 2.91 | 3.565 (7) | 127 |
C162—H16D···Cg2ii | 0.96 | 3.06 | 3.893 (11) | 146 |
C73—H73A···Cg2iii | 0.96 | 2.95 | 3.725 (9) | 138 |
C24—H24B···Cg1i | 0.96 | 2.65 | 3.147 (7) | 113 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x−1, y+1, z−1; (iii) x−1, y, z. |
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Multidentate Schiff base ligands and their metal complexes have been extensively studied for many years (Daier et al., 2004; Munro & Camp, 2003; Weber, 1967; Xu et al., 2001). Schiff bases can be prepared by condensation of different types of amines and carbonyl compounds; one of the most popular methods has been the use of salicylideneamines, which can serve as efficient models for biologically important systems (Long, 1995) in addition to their diverse chelating ability (Kim et al., 2001). The title compound, (I), was unexpectedly obtained in the reaction of 3,5-di-tert-butylsalicylaldehyde with 6-amino-2-methylpyridine.
The title compound, (I), possesses three aryl rings, viz. benzene ring 1 (atoms C1–C6; denoted R1), benzene ring 2 (C10–C15; R2) and pyridyl ring 3 (N2/C19–C23; R3). These are connected to the central polyhedron (N1/C9/C18/O1/O2/C3/C4/C10/C11) to give a propeller-like conformation, which is influenced by one intramolecular C—H···N and four intramolecular C—H···O hydrogen bonds (Fig. 3 and Table 1). The dihedral angles for R1/R2, R1/R3 and R2/R3 are 79.4 (1), 27.8 (1) and 73.0 (1)°, respectively. The bond lengths and angles are unexceptional.
C—H···π interactions often play an important role in the formation of crystal structures (Low et al., 2004; Sylvestre et al., 2005). In the case of (I), an extended crystal structure (Fig. 4) is formed through weak intermolecular C—H···π interactions (Table 1; Cg1 is the centroid of R1 and Cg2 is the centroid of R2).