


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808007204/hk2432sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536808007204/hk2432Isup2.hkl |
CCDC reference: 684541
Key indicators
- Single-crystal X-ray study
- T = 113 K
- Mean
(C-C) = 0.003 Å
- Disorder in main residue
- R factor = 0.038
- wR factor = 0.096
- Data-to-parameter ratio = 14.5
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT024_ALERT_4_B Merging of Friedel Pairs is STRONGLY Indicated . ! PLAT215_ALERT_3_B Disordered C13' has ADP max/min Ratio ....... 4.30 PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C13
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.03 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.53 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C14' PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C12 PLAT301_ALERT_3_C Main Residue Disorder ......................... 9.00 Perc.
Alert level G REFLT03_ALERT_4_G ALERT: MoKa measured Friedel data cannot be used to determine absolute structure in a light-atom study EXCEPT under VERY special conditions. It is preferred that Friedel data is merged in such cases. From the CIF: _diffrn_reflns_theta_max 25.02 From the CIF: _reflns_number_total 4618 Count of symmetry unique reflns 2426 Completeness (_total/calc) 190.35% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2192 Fraction of Friedel pairs measured 0.904 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 6 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 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
2,6-Diisopropylaniline (3.94 g, 22.2 mmol) was added via syringe to a solution of 5-tert-butyl-2-hydroxy-3-(morpholinomethyl)benzaldehyde (6.15 g, 22.2 mmol) in EtOH (100 ml). The solution was refluxed for 12 h, and then dried over magnesium sulfate, filtered and the volatiles were removed under reduced pressure. Extraction into pentane (10 ml) was followed by cooling to 243 K afforded yellow crystals of (I) (yield; 70%). Spectroscopic analysis: IR (KBr, ν, cm-1): 3055.8, 3027.2, 2961.6, 2864.9, 1618.8, 1584.9, 1468.4, 1358.9, 1276.7, 1119.2, 865.7; 1H NMR (CDCl3, δ, p.p.m.): 1.291 (d, J=6.5 Hz, 12H), 1.355 (s, 9H), 2.619 (s, 4H), 2.933–2.995 (m, 2H), 3.672 (s, 2H), 3.792–3.810 (t, 4H), 7.204(s, 3H), 7.320–7.325 (d, J=2.5 Hz, 1H), 7.539–7.534 (d, J=2.5 Hz, 1H), 8.278 (s, 1H), 9.83(s, 1H)
When the crystal structure was solved, the three methyl groups of tert-butyl bonded to the phenoxy ring were found to be disordered. They were each modelled with disorder over two positions with a common carbon atom and occupancies of 50:50. H atoms were positioned geometrically, with O—H = 0.82 Å (for OH) and C—H = 0.93, 0.98, 0.97 and 0.96 Å for aromatic, methine, methylene and methyl H, respectively, and constrained to ride on their parent atoms with Uiso(H) = xUeq(C,O), where x = 1.5 for OH and methyl H and x = 1.2 for all other H atoms.
Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![]() | Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 35% probability level. |
C28H40N2O2 | Dx = 1.106 Mg m−3 |
Mr = 436.62 | Melting point: 364 K |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 5337 reflections |
a = 10.086 (2) Å | θ = 1.9–29.7° |
b = 20.394 (4) Å | µ = 0.07 mm−1 |
c = 12.750 (3) Å | T = 113 K |
V = 2622.8 (10) Å3 | Block, yellow |
Z = 4 | 0.12 × 0.10 × 0.06 mm |
F(000) = 952 |
Rigaku Saturn diffractometer | 4314 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.040 |
ω scans | θmax = 25.0°, θmin = 2.3° |
Absorption correction: multi-scan (Blessing, 1995) | h = −12→11 |
Tmin = 0.992, Tmax = 0.996 | k = −24→24 |
25483 measured reflections | l = −15→15 |
4618 independent reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.037 | w = 1/[σ2(Fo2) + (0.0588P)2 + 0.2207P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.095 | (Δ/σ)max = 0.002 |
S = 1.04 | Δρmax = 0.18 e Å−3 |
4618 reflections | Δρmin = −0.13 e Å−3 |
318 parameters | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0157 (15) |
Secondary atom site location: difference Fourier map |
C28H40N2O2 | V = 2622.8 (10) Å3 |
Mr = 436.62 | Z = 4 |
Orthorhombic, Pna21 | Mo Kα radiation |
a = 10.086 (2) Å | µ = 0.07 mm−1 |
b = 20.394 (4) Å | T = 113 K |
c = 12.750 (3) Å | 0.12 × 0.10 × 0.06 mm |
Rigaku Saturn diffractometer | 4618 independent reflections |
Absorption correction: multi-scan (Blessing, 1995) | 4314 reflections with I > 2σ(I) |
Tmin = 0.992, Tmax = 0.996 | Rint = 0.040 |
25483 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 318 parameters |
wR(F2) = 0.095 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.18 e Å−3 |
4618 reflections | Δρmin = −0.13 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 | Occ. (<1) | |
O1 | 0.66312 (13) | 0.02738 (7) | 0.58337 (11) | 0.0474 (4) | |
O2 | 0.44036 (11) | 0.16255 (6) | 1.01270 (9) | 0.0279 (3) | |
H2 | 0.4303 | 0.1919 | 1.0559 | 0.042* | |
N1 | 0.47500 (13) | 0.04647 (6) | 0.74844 (11) | 0.0265 (3) | |
N2 | 0.32848 (13) | 0.25917 (7) | 1.10594 (11) | 0.0280 (3) | |
C1 | 0.53145 (19) | 0.10072 (9) | 0.68955 (16) | 0.0403 (5) | |
H1A | 0.6101 | 0.1168 | 0.7251 | 0.048* | |
H1B | 0.4678 | 0.1363 | 0.6857 | 0.048* | |
C2 | 0.5673 (2) | 0.07857 (11) | 0.58034 (18) | 0.0527 (6) | |
H2A | 0.4883 | 0.0632 | 0.5447 | 0.063* | |
H2B | 0.6025 | 0.1154 | 0.5410 | 0.063* | |
C3 | 0.6091 (2) | −0.02659 (9) | 0.63968 (16) | 0.0406 (5) | |
H3A | 0.6740 | −0.0616 | 0.6427 | 0.049* | |
H3B | 0.5317 | −0.0430 | 0.6028 | 0.049* | |
C4 | 0.57015 (19) | −0.00743 (9) | 0.74948 (15) | 0.0355 (4) | |
H4A | 0.5314 | −0.0449 | 0.7848 | 0.043* | |
H4B | 0.6485 | 0.0057 | 0.7882 | 0.043* | |
C5 | 0.44409 (19) | 0.06580 (9) | 0.85631 (14) | 0.0352 (4) | |
H5A | 0.5235 | 0.0834 | 0.8887 | 0.042* | |
H5B | 0.4181 | 0.0271 | 0.8956 | 0.042* | |
C6 | 0.33465 (16) | 0.11632 (8) | 0.86387 (13) | 0.0262 (4) | |
C7 | 0.33721 (15) | 0.16278 (8) | 0.94452 (12) | 0.0234 (3) | |
C8 | 0.23469 (15) | 0.20886 (8) | 0.95331 (13) | 0.0234 (3) | |
C9 | 0.12971 (16) | 0.20779 (7) | 0.88116 (13) | 0.0247 (3) | |
H9A | 0.0617 | 0.2383 | 0.8879 | 0.030* | |
C10 | 0.12458 (15) | 0.16266 (7) | 0.80036 (13) | 0.0254 (4) | |
C11 | 0.22915 (16) | 0.11738 (8) | 0.79479 (13) | 0.0260 (4) | |
H11A | 0.2273 | 0.0863 | 0.7415 | 0.031* | |
C12 | 0.01307 (17) | 0.16019 (8) | 0.71896 (14) | 0.0307 (4) | |
C13 | −0.0397 (15) | 0.0916 (5) | 0.6974 (9) | 0.071 (3) | 0.50 |
H13A | −0.0129 | 0.0779 | 0.6285 | 0.106* | 0.50 |
H13B | −0.1348 | 0.0919 | 0.7015 | 0.106* | 0.50 |
H13C | −0.0049 | 0.0617 | 0.7485 | 0.106* | 0.50 |
C14 | 0.0691 (10) | 0.1924 (4) | 0.6171 (6) | 0.061 (2) | 0.50 |
H14A | 0.1041 | 0.2350 | 0.6334 | 0.092* | 0.50 |
H14B | −0.0006 | 0.1966 | 0.5663 | 0.092* | 0.50 |
H14C | 0.1384 | 0.1654 | 0.5889 | 0.092* | 0.50 |
C15 | −0.1030 (10) | 0.2032 (6) | 0.7539 (9) | 0.0307 (19) | 0.50 |
H15A | −0.0786 | 0.2486 | 0.7479 | 0.046* | 0.50 |
H15B | −0.1247 | 0.1935 | 0.8256 | 0.046* | 0.50 |
H15C | −0.1785 | 0.1946 | 0.7102 | 0.046* | 0.50 |
C13' | −0.0535 (11) | 0.0920 (4) | 0.7330 (8) | 0.049 (2) | 0.50 |
H13D | −0.0796 | 0.0865 | 0.8049 | 0.074* | 0.50 |
H13E | 0.0082 | 0.0582 | 0.7142 | 0.074* | 0.50 |
H13F | −0.1303 | 0.0892 | 0.6888 | 0.074* | 0.50 |
C14' | 0.0708 (11) | 0.1619 (4) | 0.6092 (6) | 0.063 (2) | 0.50 |
H14D | 0.1136 | 0.2033 | 0.5977 | 0.095* | 0.50 |
H14E | 0.0010 | 0.1562 | 0.5588 | 0.095* | 0.50 |
H14F | 0.1344 | 0.1271 | 0.6015 | 0.095* | 0.50 |
C15' | −0.0942 (12) | 0.2112 (6) | 0.7301 (10) | 0.046 (3) | 0.50 |
H15D | −0.0563 | 0.2541 | 0.7220 | 0.069* | 0.50 |
H15E | −0.1340 | 0.2077 | 0.7982 | 0.069* | 0.50 |
H15F | −0.1605 | 0.2044 | 0.6772 | 0.069* | 0.50 |
C16 | 0.23491 (16) | 0.25686 (8) | 1.03797 (13) | 0.0264 (4) | |
H16A | 0.1653 | 0.2866 | 1.0428 | 0.032* | |
C17 | 0.32130 (16) | 0.30595 (9) | 1.18948 (13) | 0.0288 (4) | |
C18 | 0.30559 (17) | 0.28018 (9) | 1.29173 (15) | 0.0327 (4) | |
C19 | 0.29501 (18) | 0.32502 (10) | 1.37352 (15) | 0.0379 (4) | |
H19A | 0.2815 | 0.3096 | 1.4413 | 0.045* | |
C20 | 0.3040 (2) | 0.39149 (10) | 1.35681 (15) | 0.0409 (5) | |
H20A | 0.2946 | 0.4205 | 1.4126 | 0.049* | |
C21 | 0.3271 (2) | 0.41500 (9) | 1.25706 (16) | 0.0400 (5) | |
H21A | 0.3356 | 0.4600 | 1.2470 | 0.048* | |
C22 | 0.33791 (17) | 0.37310 (9) | 1.17069 (15) | 0.0331 (4) | |
C23 | 0.3753 (2) | 0.40061 (9) | 1.06383 (15) | 0.0389 (5) | |
H23A | 0.3678 | 0.3650 | 1.0126 | 0.047* | |
C24 | 0.5192 (2) | 0.42388 (10) | 1.06373 (17) | 0.0443 (5) | |
H24A | 0.5760 | 0.3885 | 1.0851 | 0.066* | |
H24B | 0.5288 | 0.4599 | 1.1116 | 0.066* | |
H24C | 0.5433 | 0.4378 | 0.9944 | 0.066* | |
C25 | 0.2825 (2) | 0.45530 (12) | 1.0295 (2) | 0.0597 (6) | |
H25A | 0.1927 | 0.4397 | 1.0304 | 0.090* | |
H25B | 0.3052 | 0.4690 | 0.9597 | 0.090* | |
H25C | 0.2910 | 0.4918 | 1.0766 | 0.090* | |
C26 | 0.29776 (18) | 0.20684 (9) | 1.30904 (15) | 0.0373 (4) | |
H26A | 0.3423 | 0.1858 | 1.2496 | 0.045* | |
C27 | 0.1547 (2) | 0.18351 (11) | 1.3088 (2) | 0.0601 (6) | |
H27A | 0.1120 | 0.1978 | 1.2455 | 0.090* | |
H27B | 0.1092 | 0.2015 | 1.3683 | 0.090* | |
H27C | 0.1527 | 0.1365 | 1.3123 | 0.090* | |
C28 | 0.3684 (2) | 0.18417 (11) | 1.40882 (18) | 0.0525 (6) | |
H28A | 0.4588 | 0.1988 | 1.4075 | 0.079* | |
H28B | 0.3662 | 0.1372 | 1.4126 | 0.079* | |
H28C | 0.3245 | 0.2023 | 1.4690 | 0.079* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0416 (8) | 0.0574 (9) | 0.0433 (8) | 0.0162 (7) | 0.0116 (7) | −0.0014 (7) |
O2 | 0.0244 (6) | 0.0340 (7) | 0.0254 (6) | 0.0025 (5) | −0.0045 (5) | −0.0040 (5) |
N1 | 0.0278 (7) | 0.0262 (7) | 0.0254 (7) | 0.0053 (6) | 0.0026 (6) | −0.0005 (6) |
N2 | 0.0264 (7) | 0.0319 (7) | 0.0259 (7) | −0.0017 (6) | −0.0010 (6) | −0.0038 (6) |
C1 | 0.0386 (10) | 0.0301 (9) | 0.0523 (13) | 0.0022 (8) | 0.0144 (10) | 0.0011 (8) |
C2 | 0.0518 (12) | 0.0587 (13) | 0.0476 (13) | 0.0186 (10) | 0.0214 (11) | 0.0139 (11) |
C3 | 0.0388 (10) | 0.0409 (10) | 0.0421 (11) | 0.0123 (8) | −0.0039 (9) | −0.0128 (9) |
C4 | 0.0370 (9) | 0.0323 (9) | 0.0373 (10) | 0.0112 (8) | −0.0018 (8) | −0.0023 (8) |
C5 | 0.0361 (10) | 0.0428 (10) | 0.0267 (9) | 0.0127 (8) | −0.0016 (8) | −0.0039 (8) |
C6 | 0.0252 (8) | 0.0300 (8) | 0.0233 (8) | 0.0032 (6) | 0.0026 (7) | −0.0004 (7) |
C7 | 0.0224 (8) | 0.0275 (8) | 0.0204 (8) | −0.0040 (6) | −0.0003 (7) | 0.0030 (6) |
C8 | 0.0227 (8) | 0.0241 (8) | 0.0235 (8) | −0.0035 (6) | 0.0021 (7) | 0.0003 (6) |
C9 | 0.0218 (8) | 0.0250 (8) | 0.0271 (9) | 0.0006 (6) | 0.0011 (7) | −0.0020 (7) |
C10 | 0.0236 (8) | 0.0291 (8) | 0.0234 (8) | −0.0026 (6) | 0.0020 (7) | −0.0013 (7) |
C11 | 0.0296 (9) | 0.0257 (8) | 0.0227 (8) | −0.0010 (6) | 0.0002 (7) | −0.0034 (7) |
C12 | 0.0269 (8) | 0.0373 (9) | 0.0281 (9) | 0.0023 (7) | −0.0035 (7) | −0.0084 (7) |
C13 | 0.069 (5) | 0.051 (4) | 0.092 (7) | 0.011 (3) | −0.032 (5) | −0.040 (4) |
C14 | 0.042 (3) | 0.118 (6) | 0.024 (3) | 0.011 (4) | −0.008 (2) | 0.005 (3) |
C15 | 0.031 (3) | 0.035 (4) | 0.026 (4) | 0.005 (2) | −0.017 (2) | −0.001 (2) |
C13' | 0.041 (4) | 0.034 (3) | 0.072 (5) | 0.001 (2) | −0.045 (4) | −0.017 (3) |
C14' | 0.044 (3) | 0.109 (6) | 0.036 (3) | 0.009 (4) | −0.005 (2) | 0.002 (4) |
C15' | 0.057 (4) | 0.035 (4) | 0.045 (6) | 0.014 (3) | −0.017 (3) | −0.006 (4) |
C16 | 0.0256 (8) | 0.0252 (8) | 0.0285 (9) | −0.0029 (6) | 0.0005 (7) | −0.0022 (7) |
C17 | 0.0242 (8) | 0.0360 (9) | 0.0261 (9) | −0.0023 (7) | −0.0027 (7) | −0.0071 (7) |
C18 | 0.0262 (9) | 0.0412 (10) | 0.0306 (10) | −0.0007 (7) | −0.0020 (8) | −0.0046 (8) |
C19 | 0.0355 (9) | 0.0514 (11) | 0.0267 (9) | −0.0003 (8) | 0.0009 (8) | −0.0082 (9) |
C20 | 0.0445 (11) | 0.0454 (11) | 0.0330 (11) | −0.0009 (9) | 0.0032 (9) | −0.0143 (9) |
C21 | 0.0484 (11) | 0.0324 (9) | 0.0392 (11) | −0.0010 (8) | −0.0012 (9) | −0.0095 (8) |
C22 | 0.0349 (9) | 0.0350 (9) | 0.0295 (9) | −0.0026 (7) | −0.0029 (8) | −0.0047 (7) |
C23 | 0.0489 (11) | 0.0355 (10) | 0.0323 (10) | −0.0052 (8) | −0.0032 (9) | −0.0072 (8) |
C24 | 0.0429 (11) | 0.0461 (11) | 0.0440 (11) | 0.0007 (9) | 0.0053 (10) | −0.0051 (9) |
C25 | 0.0538 (13) | 0.0767 (16) | 0.0485 (13) | 0.0090 (12) | −0.0107 (11) | 0.0142 (12) |
C26 | 0.0377 (10) | 0.0422 (10) | 0.0319 (10) | 0.0010 (8) | 0.0023 (9) | −0.0007 (9) |
C27 | 0.0497 (13) | 0.0569 (13) | 0.0738 (17) | −0.0160 (11) | −0.0136 (13) | 0.0043 (13) |
C28 | 0.0514 (12) | 0.0545 (13) | 0.0516 (13) | −0.0024 (10) | −0.0053 (11) | 0.0130 (11) |
O1—C3 | 1.423 (3) | C14—H14C | 0.9600 |
O1—C2 | 1.423 (2) | C15—H15A | 0.9600 |
O2—C7 | 1.3558 (19) | C15—H15B | 0.9600 |
O2—H2 | 0.8200 | C15—H15C | 0.9600 |
N1—C1 | 1.453 (2) | C13'—H13D | 0.9600 |
N1—C4 | 1.459 (2) | C13'—H13E | 0.9600 |
N1—C5 | 1.464 (2) | C13'—H13F | 0.9600 |
N2—C16 | 1.282 (2) | C14'—H14D | 0.9600 |
N2—C17 | 1.432 (2) | C14'—H14E | 0.9600 |
C1—C2 | 1.508 (3) | C14'—H14F | 0.9600 |
C1—H1A | 0.9700 | C15'—H15D | 0.9600 |
C1—H1B | 0.9700 | C15'—H15E | 0.9600 |
C2—H2A | 0.9700 | C15'—H15F | 0.9600 |
C2—H2B | 0.9700 | C16—H16A | 0.9300 |
C3—C4 | 1.506 (3) | C17—C22 | 1.400 (3) |
C3—H3A | 0.9700 | C17—C18 | 1.415 (3) |
C3—H3B | 0.9700 | C18—C19 | 1.391 (3) |
C4—H4A | 0.9700 | C18—C26 | 1.514 (3) |
C4—H4B | 0.9700 | C19—C20 | 1.375 (3) |
C5—C6 | 1.513 (2) | C19—H19A | 0.9300 |
C5—H5A | 0.9700 | C20—C21 | 1.379 (3) |
C5—H5B | 0.9700 | C20—H20A | 0.9300 |
C6—C11 | 1.382 (2) | C21—C22 | 1.398 (3) |
C6—C7 | 1.398 (2) | C21—H21A | 0.9300 |
C7—C8 | 1.402 (2) | C22—C23 | 1.521 (3) |
C8—C9 | 1.403 (2) | C23—C25 | 1.521 (3) |
C8—C16 | 1.457 (2) | C23—C24 | 1.527 (3) |
C9—C10 | 1.382 (2) | C23—H23A | 0.9800 |
C9—H9A | 0.9300 | C24—H24A | 0.9600 |
C10—C11 | 1.404 (2) | C24—H24B | 0.9600 |
C10—C12 | 1.531 (2) | C24—H24C | 0.9600 |
C11—H11A | 0.9300 | C25—H25A | 0.9600 |
C12—C15' | 1.508 (8) | C25—H25B | 0.9600 |
C12—C14' | 1.517 (7) | C25—H25C | 0.9600 |
C12—C13 | 1.522 (8) | C26—C27 | 1.519 (3) |
C12—C15 | 1.530 (7) | C26—C28 | 1.530 (3) |
C12—C13' | 1.554 (7) | C26—H26A | 0.9800 |
C12—C14 | 1.561 (7) | C27—H27A | 0.9600 |
C13—H13A | 0.9600 | C27—H27B | 0.9600 |
C13—H13B | 0.9600 | C27—H27C | 0.9600 |
C13—H13C | 0.9600 | C28—H28A | 0.9600 |
C14—H14A | 0.9600 | C28—H28B | 0.9600 |
C14—H14B | 0.9600 | C28—H28C | 0.9600 |
C3—O1—C2 | 108.71 (14) | H14B—C14—H14C | 109.5 |
C7—O2—H2 | 109.5 | C12—C15—H15A | 109.5 |
C1—N1—C4 | 108.69 (14) | C12—C15—H15B | 109.5 |
C1—N1—C5 | 111.33 (14) | H15A—C15—H15B | 109.5 |
C4—N1—C5 | 109.53 (13) | C12—C15—H15C | 109.5 |
C16—N2—C17 | 119.34 (13) | H15A—C15—H15C | 109.5 |
N1—C1—C2 | 110.06 (16) | H15B—C15—H15C | 109.5 |
N1—C1—H1A | 109.6 | C12—C13'—H13D | 109.5 |
C2—C1—H1A | 109.6 | C12—C13'—H13E | 109.5 |
N1—C1—H1B | 109.6 | H13D—C13'—H13E | 109.5 |
C2—C1—H1B | 109.6 | C12—C13'—H13F | 109.5 |
H1A—C1—H1B | 108.2 | H13D—C13'—H13F | 109.5 |
O1—C2—C1 | 110.94 (17) | H13E—C13'—H13F | 109.5 |
O1—C2—H2A | 109.5 | C12—C14'—H14D | 109.5 |
C1—C2—H2A | 109.5 | C12—C14'—H14E | 109.5 |
O1—C2—H2B | 109.5 | H14D—C14'—H14E | 109.5 |
C1—C2—H2B | 109.5 | C12—C14'—H14F | 109.5 |
H2A—C2—H2B | 108.0 | H14D—C14'—H14F | 109.5 |
O1—C3—C4 | 111.61 (15) | H14E—C14'—H14F | 109.5 |
O1—C3—H3A | 109.3 | C12—C15'—H15D | 109.5 |
C4—C3—H3A | 109.3 | C12—C15'—H15E | 109.5 |
O1—C3—H3B | 109.3 | H15D—C15'—H15E | 109.5 |
C4—C3—H3B | 109.3 | C12—C15'—H15F | 109.5 |
H3A—C3—H3B | 108.0 | H15D—C15'—H15F | 109.5 |
N1—C4—C3 | 111.01 (15) | H15E—C15'—H15F | 109.5 |
N1—C4—H4A | 109.4 | N2—C16—C8 | 121.77 (14) |
C3—C4—H4A | 109.4 | N2—C16—H16A | 119.1 |
N1—C4—H4B | 109.4 | C8—C16—H16A | 119.1 |
C3—C4—H4B | 109.4 | C22—C17—C18 | 122.30 (15) |
H4A—C4—H4B | 108.0 | C22—C17—N2 | 121.22 (15) |
N1—C5—C6 | 113.49 (14) | C18—C17—N2 | 116.34 (15) |
N1—C5—H5A | 108.9 | C19—C18—C17 | 117.09 (16) |
C6—C5—H5A | 108.9 | C19—C18—C26 | 122.42 (17) |
N1—C5—H5B | 108.9 | C17—C18—C26 | 120.48 (15) |
C6—C5—H5B | 108.9 | C20—C19—C18 | 121.78 (18) |
H5A—C5—H5B | 107.7 | C20—C19—H19A | 119.1 |
C11—C6—C7 | 118.20 (14) | C18—C19—H19A | 119.1 |
C11—C6—C5 | 122.14 (15) | C19—C20—C21 | 119.79 (17) |
C7—C6—C5 | 119.65 (14) | C19—C20—H20A | 120.1 |
O2—C7—C6 | 118.90 (14) | C21—C20—H20A | 120.1 |
O2—C7—C8 | 121.14 (14) | C20—C21—C22 | 121.81 (18) |
C6—C7—C8 | 119.95 (14) | C20—C21—H21A | 119.1 |
C7—C8—C9 | 119.60 (14) | C22—C21—H21A | 119.1 |
C7—C8—C16 | 120.56 (14) | C21—C22—C17 | 116.98 (18) |
C9—C8—C16 | 119.83 (14) | C21—C22—C23 | 119.96 (16) |
C10—C9—C8 | 121.83 (14) | C17—C22—C23 | 122.93 (16) |
C10—C9—H9A | 119.1 | C25—C23—C22 | 112.08 (18) |
C8—C9—H9A | 119.1 | C25—C23—C24 | 110.91 (17) |
C9—C10—C11 | 116.59 (14) | C22—C23—C24 | 110.57 (16) |
C9—C10—C12 | 123.67 (14) | C25—C23—H23A | 107.7 |
C11—C10—C12 | 119.74 (14) | C22—C23—H23A | 107.7 |
C6—C11—C10 | 123.83 (15) | C24—C23—H23A | 107.7 |
C6—C11—H11A | 118.1 | C23—C24—H24A | 109.5 |
C10—C11—H11A | 118.1 | C23—C24—H24B | 109.5 |
C15'—C12—C14' | 110.3 (6) | H24A—C24—H24B | 109.5 |
C15'—C12—C13 | 113.6 (9) | C23—C24—H24C | 109.5 |
C14'—C12—C13 | 89.3 (6) | H24A—C24—H24C | 109.5 |
C14'—C12—C15 | 123.4 (6) | H24B—C24—H24C | 109.5 |
C13—C12—C15 | 108.2 (8) | C23—C25—H25A | 109.5 |
C15'—C12—C10 | 116.1 (6) | C23—C25—H25B | 109.5 |
C14'—C12—C10 | 110.0 (5) | H25A—C25—H25B | 109.5 |
C13—C12—C10 | 114.2 (6) | C23—C25—H25C | 109.5 |
C15—C12—C10 | 110.2 (5) | H25A—C25—H25C | 109.5 |
C15'—C12—C13' | 107.2 (7) | H25B—C25—H25C | 109.5 |
C14'—C12—C13' | 107.0 (6) | C18—C26—C27 | 111.01 (17) |
C15—C12—C13' | 98.6 (7) | C18—C26—C28 | 113.29 (16) |
C10—C12—C13' | 105.6 (4) | C27—C26—C28 | 110.46 (18) |
C15'—C12—C14 | 92.7 (6) | C18—C26—H26A | 107.3 |
C13—C12—C14 | 111.3 (6) | C27—C26—H26A | 107.3 |
C15—C12—C14 | 106.2 (6) | C28—C26—H26A | 107.3 |
C10—C12—C14 | 106.5 (4) | C26—C27—H27A | 109.5 |
C13'—C12—C14 | 129.0 (5) | C26—C27—H27B | 109.5 |
C12—C13—H13A | 109.5 | H27A—C27—H27B | 109.5 |
C12—C13—H13B | 109.5 | C26—C27—H27C | 109.5 |
H13A—C13—H13B | 109.5 | H27A—C27—H27C | 109.5 |
C12—C13—H13C | 109.5 | H27B—C27—H27C | 109.5 |
H13A—C13—H13C | 109.5 | C26—C28—H28A | 109.5 |
H13B—C13—H13C | 109.5 | C26—C28—H28B | 109.5 |
C12—C14—H14A | 109.5 | H28A—C28—H28B | 109.5 |
C12—C14—H14B | 109.5 | C26—C28—H28C | 109.5 |
H14A—C14—H14B | 109.5 | H28A—C28—H28C | 109.5 |
C12—C14—H14C | 109.5 | H28B—C28—H28C | 109.5 |
H14A—C14—H14C | 109.5 | ||
C4—N1—C1—C2 | 57.0 (2) | C9—C10—C12—C15 | −12.5 (6) |
C5—N1—C1—C2 | 177.71 (15) | C11—C10—C12—C15 | 167.6 (5) |
C3—O1—C2—C1 | 60.1 (2) | C9—C10—C12—C13' | −118.0 (5) |
N1—C1—C2—O1 | −60.7 (2) | C11—C10—C12—C13' | 62.1 (5) |
C2—O1—C3—C4 | −58.5 (2) | C9—C10—C12—C14 | 102.2 (4) |
C1—N1—C4—C3 | −55.6 (2) | C11—C10—C12—C14 | −77.6 (4) |
C5—N1—C4—C3 | −177.41 (16) | C17—N2—C16—C8 | −177.94 (15) |
O1—C3—C4—N1 | 57.4 (2) | C7—C8—C16—N2 | 0.8 (2) |
C1—N1—C5—C6 | 66.21 (19) | C9—C8—C16—N2 | 179.50 (15) |
C4—N1—C5—C6 | −173.56 (15) | C16—N2—C17—C22 | −70.8 (2) |
N1—C5—C6—C11 | 34.2 (2) | C16—N2—C17—C18 | 113.33 (18) |
N1—C5—C6—C7 | −147.46 (15) | C22—C17—C18—C19 | 5.7 (3) |
C11—C6—C7—O2 | −179.73 (14) | N2—C17—C18—C19 | −178.39 (15) |
C5—C6—C7—O2 | 1.8 (2) | C22—C17—C18—C26 | −175.61 (16) |
C11—C6—C7—C8 | −0.2 (2) | N2—C17—C18—C26 | 0.3 (2) |
C5—C6—C7—C8 | −178.66 (15) | C17—C18—C19—C20 | −2.2 (3) |
O2—C7—C8—C9 | 179.79 (14) | C26—C18—C19—C20 | 179.14 (18) |
C6—C7—C8—C9 | 0.3 (2) | C18—C19—C20—C21 | −1.5 (3) |
O2—C7—C8—C16 | −1.5 (2) | C19—C20—C21—C22 | 1.9 (3) |
C6—C7—C8—C16 | 178.97 (14) | C20—C21—C22—C17 | 1.4 (3) |
C7—C8—C9—C10 | −0.6 (2) | C20—C21—C22—C23 | −174.63 (19) |
C16—C8—C9—C10 | −179.24 (15) | C18—C17—C22—C21 | −5.3 (3) |
C8—C9—C10—C11 | 0.7 (2) | N2—C17—C22—C21 | 179.01 (15) |
C8—C9—C10—C12 | −179.16 (15) | C18—C17—C22—C23 | 170.59 (17) |
C7—C6—C11—C10 | 0.4 (2) | N2—C17—C22—C23 | −5.1 (3) |
C5—C6—C11—C10 | 178.80 (16) | C21—C22—C23—C25 | −55.3 (2) |
C9—C10—C11—C6 | −0.6 (2) | C17—C22—C23—C25 | 128.9 (2) |
C12—C10—C11—C6 | 179.22 (15) | C21—C22—C23—C24 | 69.0 (2) |
C9—C10—C12—C15' | 0.6 (6) | C17—C22—C23—C24 | −106.78 (19) |
C11—C10—C12—C15' | −179.2 (6) | C19—C18—C26—C27 | 85.8 (2) |
C9—C10—C12—C14' | 126.8 (4) | C17—C18—C26—C27 | −92.8 (2) |
C11—C10—C12—C14' | −53.0 (4) | C19—C18—C26—C28 | −39.2 (3) |
C9—C10—C12—C13 | −134.6 (6) | C17—C18—C26—C28 | 142.27 (18) |
C11—C10—C12—C13 | 45.6 (6) |
Experimental details
Crystal data | |
Chemical formula | C28H40N2O2 |
Mr | 436.62 |
Crystal system, space group | Orthorhombic, Pna21 |
Temperature (K) | 113 |
a, b, c (Å) | 10.086 (2), 20.394 (4), 12.750 (3) |
V (Å3) | 2622.8 (10) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.12 × 0.10 × 0.06 |
Data collection | |
Diffractometer | Rigaku Saturn diffractometer |
Absorption correction | Multi-scan (Blessing, 1995) |
Tmin, Tmax | 0.992, 0.996 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 25483, 4618, 4314 |
Rint | 0.040 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.095, 1.04 |
No. of reflections | 4618 |
No. of parameters | 318 |
No. of restraints | ? |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.18, −0.13 |
Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
The simple and readily accessible salicylaldiminato ligand family has played an important role in the development of transition metal coordination chemistry, and recently they have been shown to support highly active polymerization centers for both the early and late transition metals (Younkin et al., 2000). Increasing the sizes of the imino and the o-phenoxy substituents has a pronounced effect on the activity of the catalyst and the molecular weight of the polymer (Gibson & Spitzmesser, 2003). We have recently prepared the novel title ligand, (I), and report herein its crystal structure
In the molecule of the title compound, (I), (Fig. 1) the bond lengths and angles are within normal ranges. When the crystal structure was solved, the three methyl groups of tert-butyl bonded to the phenoxy ring were found to be disordered.
Ring A (O1/N1/C1—C4) is not planar, having total puckering amplitude, QT, of 1.022 (3) Å. It adopts chair [ϕ = 29.58 (2)° and θ = 56.99 (3)°] conformation (Cremer & Pople, 1975). The intramolecular O—H···N hydrogen bond (Table 1) results in the formation of a planar six-membered ring C (O2/H2/N2/C7/C8/C16), which is oriented with respect to rings B (C6—C11) and D (C17—C22) at dihedral angles of B/C = 0.70 (3)° and C/D = 67.93 (4)°. So, rings B and C are also nearly coplanar. The dihedral angle between rings B and D is B/D = 67.66 (3)°.