Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807051306/cs2047sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807051306/cs2047Isup2.hkl |
CCDC reference: 667418
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.005 Å
- Disorder in main residue
- R factor = 0.038
- wR factor = 0.105
- Data-to-parameter ratio = 7.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.85 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.94 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.23 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 C10 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C20 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C7' PLAT301_ALERT_3_C Main Residue Disorder ......................... 8.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5 PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond C5 - C6 ... 1.39 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 7
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.01 From the CIF: _reflns_number_total 2505 Count of symmetry unique reflns 2503 Completeness (_total/calc) 100.08% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2 Fraction of Friedel pairs measured 0.001 Are heavy atom types Z>Si present no PLAT792_ALERT_1_G Check the Absolute Configuration of C24 = ... S PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 41
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 12 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 5 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Gibson & Spitzmesser (2003); Ittel & Johnson (2000); Shriner et al. (1946).
2,6-Diisopropylaniline (3.94 g, 22.2 mmol) was added via syringe to a solution of 5-tert-Butyl-2-hydroxy-3-(1-phenyl-ethyl)-benzaldehyde (6.26 g, 22.2 mmol) in EtOH (100 ml). Formic acid (0.01 g, 0.22 mmol) was added and the solution refluxed for 20 h. The solution was dried over magnesium sulfate, filtered and the volatiles removed under reduced pressure. Extraction into pentane (5 ml) followed by cooling to 243 K afforded yellow crystals of (I) (yield 76%). Spectroscopic analysis: IR (KBr, ν, cm-1): 3055.8, 3027.2, 2965.6, 2871.9, 1621.5, 1591.1, 1460.4, 1361.9, 1269.7, 1176.9, 855.7; 1H NMR (CDCl3, δ, p.p.m.): 1.188 (s, 12H), 1.305 (s, 9H), 1.692 (s, 3H), 3.021 (s, 2H), 4.756 (s, 1H), 7.182–7.369 (m, 10H), 8.287 (s, 1H), 13.146 (s, 1H)
Except the hydroxyl H atom, all H atoms were positioned geometrically (C—H=0.93–0.97 Å) and refined as riding. Uiso(H) values are equal to 1.2Ueq(carrier atom). In absence of significant anomalous dispersion effects, Friedel-pair reflections were merged prior to refinement.
Late-metal catalysts bearing salicylaldiminato-type ligands play an important role in the catalytic oligomerization and polymerization of olefins (Ittel et al., 2000). Increasing the size of the imino substituent and the o-phenoxy substituent has a pronounced effect on the activity of the catalyst and the molecular weight of the polymer (Gibson et al., 2003). We have recently prepared a novel ligand, (I), and report its crystal structure here.
The molecular structure of (I) is shown in Fig. 1. In (I) the phenyl ring and the phenoxy ring form a dihedral angle of 75.18 (1)°, the phenylimino ring is nearly perpendicular to the phenoxy ring, with a dihedral angle of 81.51 (2)°. The dihedral angle between the phenyl and the phenylimino ring is 62.88 (1)°. Three C atoms of isopropyl attaching to the phenylimino ring are disordered in two locations with 55% and 45% probabilities. An intramolecular hydrogen bond is formed between the hydroxyl group and the N atom stabilizing the crystal structure.
For related literature, see: Gibson & Spitzmesser (2003); Ittel & Johnson (2000); Shriner et al. (1946).
Data collection: SMART (Bruker, 1997); cell refinement: SMART (Bruker, 1997); 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, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).
Fig. 1. View of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 35% probability level. |
C31H39NO | Dx = 1.093 Mg m−3 |
Mr = 441.63 | Melting point: 400 K |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
a = 25.273 (4) Å | Cell parameters from 3934 reflections |
b = 9.5496 (18) Å | θ = 2.3–24.1° |
c = 11.115 (2) Å | µ = 0.07 mm−1 |
V = 2682.6 (8) Å3 | T = 294 K |
Z = 4 | Block, yellow |
F(000) = 960 | 0.24 × 0.20 × 0.16 mm |
Bruker SMART APEX CCD diffractometer | 2505 independent reflections |
Radiation source: fine-focus sealed tube | 1964 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
φ and ω scans | θmax = 25.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −19→30 |
Tmin = 0.974, Tmax = 0.990 | k = −11→9 |
13332 measured reflections | l = −11→13 |
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.105 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0512P)2 + 0.4436P] where P = (Fo2 + 2Fc2)/3 |
2505 reflections | (Δ/σ)max = 0.003 |
319 parameters | Δρmax = 0.13 e Å−3 |
41 restraints | Δρmin = −0.12 e Å−3 |
C31H39NO | V = 2682.6 (8) Å3 |
Mr = 441.63 | Z = 4 |
Orthorhombic, Pca21 | Mo Kα radiation |
a = 25.273 (4) Å | µ = 0.07 mm−1 |
b = 9.5496 (18) Å | T = 294 K |
c = 11.115 (2) Å | 0.24 × 0.20 × 0.16 mm |
Bruker SMART APEX CCD diffractometer | 2505 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1964 reflections with I > 2σ(I) |
Tmin = 0.974, Tmax = 0.990 | Rint = 0.039 |
13332 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 41 restraints |
wR(F2) = 0.105 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.13 e Å−3 |
2505 reflections | Δρmin = −0.12 e Å−3 |
319 parameters |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.44217 (8) | 0.0843 (2) | 0.9096 (2) | 0.0504 (5) | |
H1 | 0.4093 (15) | 0.115 (4) | 0.937 (4) | 0.076* | |
N1 | 0.34993 (8) | 0.2094 (3) | 0.9030 (2) | 0.0441 (6) | |
C1 | 0.29497 (10) | 0.2202 (3) | 0.9371 (3) | 0.0420 (7) | |
C2 | 0.26067 (11) | 0.1171 (3) | 0.8930 (3) | 0.0456 (7) | |
C3 | 0.20812 (12) | 0.1214 (4) | 0.9313 (3) | 0.0571 (9) | |
H3A | 0.1845 | 0.0538 | 0.9039 | 0.069* | |
C4 | 0.19064 (13) | 0.2234 (4) | 1.0087 (4) | 0.0647 (10) | |
H4A | 0.1555 | 0.2246 | 1.0331 | 0.078* | |
C5 | 0.22512 (13) | 0.3240 (4) | 1.0501 (3) | 0.0597 (9) | |
H5A | 0.2126 | 0.3936 | 1.1012 | 0.072* | |
C6 | 0.27828 (12) | 0.3240 (3) | 1.0173 (3) | 0.0489 (8) | |
C7 | 0.31638 (13) | 0.4301 (4) | 1.0708 (3) | 0.0585 (9) | 0.55 |
H7A | 0.3432 | 0.4506 | 1.0096 | 0.070* | 0.55 |
C8 | 0.3442 (4) | 0.3728 (10) | 1.1771 (9) | 0.093 (3) | 0.55 |
H8A | 0.3612 | 0.2864 | 1.1558 | 0.140* | 0.55 |
H8B | 0.3192 | 0.3560 | 1.2404 | 0.140* | 0.55 |
H8C | 0.3703 | 0.4387 | 1.2042 | 0.140* | 0.55 |
C9 | 0.2903 (4) | 0.5695 (8) | 1.1056 (11) | 0.094 (3) | 0.55 |
H9A | 0.2724 | 0.6078 | 1.0370 | 0.141* | 0.55 |
H9B | 0.3169 | 0.6340 | 1.1324 | 0.141* | 0.55 |
H9C | 0.2653 | 0.5539 | 1.1692 | 0.141* | 0.55 |
C7' | 0.31638 (13) | 0.4301 (4) | 1.0708 (3) | 0.0585 (9) | 0.45 |
H7'A | 0.3517 | 0.4052 | 1.0413 | 0.070* | 0.45 |
C8' | 0.3184 (5) | 0.4162 (15) | 1.2099 (8) | 0.101 (4) | 0.45 |
H8'A | 0.3426 | 0.4838 | 1.2420 | 0.152* | 0.45 |
H8'B | 0.3299 | 0.3237 | 1.2311 | 0.152* | 0.45 |
H8'C | 0.2837 | 0.4325 | 1.2426 | 0.152* | 0.45 |
C9' | 0.3053 (5) | 0.5723 (10) | 1.0256 (14) | 0.101 (4) | 0.45 |
H9'A | 0.3053 | 0.5715 | 0.9392 | 0.152* | 0.45 |
H9'B | 0.3320 | 0.6356 | 1.0540 | 0.152* | 0.45 |
H9'C | 0.2712 | 0.6023 | 1.0540 | 0.152* | 0.45 |
C10 | 0.27988 (12) | 0.0008 (3) | 0.8111 (3) | 0.0538 (8) | |
H10A | 0.3106 | 0.0365 | 0.7670 | 0.065* | |
C11 | 0.23939 (16) | −0.0449 (5) | 0.7194 (4) | 0.0823 (13) | |
H11A | 0.2287 | 0.0343 | 0.6720 | 0.124* | |
H11B | 0.2091 | −0.0831 | 0.7599 | 0.124* | |
H11C | 0.2546 | −0.1149 | 0.6679 | 0.124* | |
C12 | 0.29860 (19) | −0.1216 (4) | 0.8871 (4) | 0.0941 (14) | |
H12A | 0.3245 | −0.0896 | 0.9440 | 0.141* | |
H12B | 0.3141 | −0.1915 | 0.8360 | 0.141* | |
H12C | 0.2690 | −0.1613 | 0.9293 | 0.141* | |
C13 | 0.36706 (10) | 0.2802 (3) | 0.8142 (3) | 0.0403 (6) | |
H13A | 0.3447 | 0.3457 | 0.7788 | 0.048* | |
C14 | 0.42028 (10) | 0.2630 (3) | 0.7657 (2) | 0.0344 (6) | |
C15 | 0.43582 (11) | 0.3420 (3) | 0.6666 (3) | 0.0390 (6) | |
H15A | 0.4126 | 0.4092 | 0.6367 | 0.047* | |
C16 | 0.48415 (11) | 0.3248 (3) | 0.6105 (3) | 0.0394 (7) | |
C17 | 0.51775 (11) | 0.2242 (3) | 0.6607 (3) | 0.0415 (7) | |
H17A | 0.5506 | 0.2102 | 0.6251 | 0.050* | |
C18 | 0.50481 (10) | 0.1442 (3) | 0.7606 (3) | 0.0378 (6) | |
C19 | 0.45548 (10) | 0.1634 (3) | 0.8132 (2) | 0.0351 (6) | |
C20 | 0.50008 (12) | 0.4134 (3) | 0.5021 (3) | 0.0501 (8) | |
C21 | 0.45576 (16) | 0.4140 (5) | 0.4080 (4) | 0.0873 (13) | |
H21A | 0.4237 | 0.4480 | 0.4440 | 0.131* | |
H21B | 0.4502 | 0.3205 | 0.3788 | 0.131* | |
H21C | 0.4655 | 0.4738 | 0.3423 | 0.131* | |
C22 | 0.50891 (19) | 0.5640 (4) | 0.5434 (4) | 0.0891 (14) | |
H22A | 0.4775 | 0.5980 | 0.5823 | 0.134* | |
H22B | 0.5168 | 0.6218 | 0.4751 | 0.134* | |
H22C | 0.5380 | 0.5669 | 0.5990 | 0.134* | |
C23 | 0.55002 (16) | 0.3593 (5) | 0.4403 (4) | 0.0898 (14) | |
H23A | 0.5787 | 0.3581 | 0.4969 | 0.135* | |
H23B | 0.5589 | 0.4197 | 0.3742 | 0.135* | |
H23C | 0.5439 | 0.2662 | 0.4109 | 0.135* | |
C24 | 0.54360 (11) | 0.0404 (3) | 0.8163 (3) | 0.0484 (7) | |
H24A | 0.5223 | −0.0311 | 0.8570 | 0.058* | |
C25 | 0.57752 (15) | −0.0359 (4) | 0.7233 (4) | 0.0720 (11) | |
H25A | 0.6009 | −0.0999 | 0.7635 | 0.108* | |
H25B | 0.5980 | 0.0310 | 0.6787 | 0.108* | |
H25C | 0.5550 | −0.0869 | 0.6692 | 0.108* | |
C26 | 0.57654 (11) | 0.1120 (3) | 0.9126 (3) | 0.0453 (7) | |
C27 | 0.61133 (12) | 0.2191 (4) | 0.8845 (3) | 0.0595 (9) | |
H27A | 0.6149 | 0.2469 | 0.8047 | 0.071* | |
C28 | 0.64090 (15) | 0.2858 (4) | 0.9719 (4) | 0.0753 (12) | |
H28A | 0.6639 | 0.3579 | 0.9511 | 0.090* | |
C29 | 0.63612 (18) | 0.2449 (5) | 1.0891 (4) | 0.0883 (14) | |
H29A | 0.6560 | 0.2889 | 1.1485 | 0.106* | |
C30 | 0.60198 (18) | 0.1388 (5) | 1.1194 (4) | 0.0839 (12) | |
H30A | 0.5987 | 0.1112 | 1.1993 | 0.101* | |
C31 | 0.57252 (13) | 0.0728 (4) | 1.0313 (3) | 0.0631 (9) | |
H31A | 0.5496 | 0.0007 | 1.0526 | 0.076* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0451 (11) | 0.0618 (13) | 0.0441 (12) | 0.0068 (10) | 0.0068 (10) | 0.0183 (11) |
N1 | 0.0306 (11) | 0.0593 (15) | 0.0424 (14) | −0.0006 (11) | 0.0055 (11) | 0.0033 (13) |
C1 | 0.0327 (14) | 0.0546 (17) | 0.0388 (16) | 0.0000 (13) | 0.0058 (12) | 0.0033 (15) |
C2 | 0.0379 (16) | 0.0617 (18) | 0.0373 (16) | −0.0015 (13) | 0.0073 (13) | 0.0017 (15) |
C3 | 0.0375 (16) | 0.079 (2) | 0.055 (2) | −0.0110 (15) | 0.0061 (16) | −0.0081 (19) |
C4 | 0.0375 (17) | 0.083 (2) | 0.073 (2) | −0.0009 (17) | 0.0173 (18) | −0.004 (2) |
C5 | 0.0496 (19) | 0.068 (2) | 0.062 (2) | 0.0047 (16) | 0.0191 (18) | −0.0052 (19) |
C6 | 0.0430 (17) | 0.0568 (19) | 0.0468 (18) | −0.0007 (14) | 0.0076 (15) | −0.0001 (16) |
C7 | 0.054 (2) | 0.058 (2) | 0.063 (2) | −0.0073 (16) | 0.0126 (17) | −0.0091 (18) |
C8 | 0.088 (6) | 0.087 (5) | 0.105 (6) | −0.007 (4) | −0.039 (5) | 0.009 (5) |
C9 | 0.103 (6) | 0.062 (4) | 0.117 (7) | 0.002 (4) | −0.016 (5) | −0.004 (5) |
C7' | 0.054 (2) | 0.058 (2) | 0.063 (2) | −0.0073 (16) | 0.0126 (17) | −0.0091 (18) |
C8' | 0.097 (7) | 0.107 (8) | 0.100 (7) | −0.017 (6) | −0.023 (6) | −0.001 (6) |
C9' | 0.104 (7) | 0.076 (6) | 0.123 (8) | −0.008 (5) | 0.000 (7) | 0.017 (6) |
C10 | 0.0483 (17) | 0.071 (2) | 0.0425 (17) | −0.0054 (15) | 0.0089 (16) | −0.0042 (18) |
C11 | 0.078 (3) | 0.102 (3) | 0.067 (2) | −0.020 (2) | 0.001 (2) | −0.028 (2) |
C12 | 0.129 (4) | 0.083 (3) | 0.070 (3) | 0.034 (3) | 0.023 (3) | −0.001 (3) |
C13 | 0.0318 (14) | 0.0524 (16) | 0.0368 (15) | 0.0004 (12) | −0.0002 (13) | 0.0025 (15) |
C14 | 0.0303 (14) | 0.0432 (14) | 0.0298 (13) | −0.0047 (11) | −0.0031 (11) | 0.0008 (13) |
C15 | 0.0345 (15) | 0.0472 (15) | 0.0351 (15) | 0.0012 (12) | −0.0038 (13) | 0.0037 (14) |
C16 | 0.0347 (15) | 0.0487 (16) | 0.0346 (15) | −0.0063 (12) | −0.0004 (13) | 0.0021 (13) |
C17 | 0.0293 (14) | 0.0566 (17) | 0.0385 (15) | −0.0018 (12) | 0.0038 (12) | 0.0012 (15) |
C18 | 0.0327 (15) | 0.0434 (15) | 0.0371 (16) | 0.0001 (11) | −0.0028 (12) | 0.0002 (14) |
C19 | 0.0337 (14) | 0.0413 (14) | 0.0303 (14) | −0.0061 (11) | −0.0007 (12) | 0.0023 (13) |
C20 | 0.0473 (18) | 0.062 (2) | 0.0412 (18) | −0.0058 (14) | 0.0078 (14) | 0.0118 (16) |
C21 | 0.081 (3) | 0.131 (4) | 0.051 (2) | −0.006 (2) | −0.005 (2) | 0.026 (3) |
C22 | 0.116 (4) | 0.070 (3) | 0.081 (3) | −0.027 (2) | 0.019 (3) | 0.021 (2) |
C23 | 0.073 (3) | 0.116 (3) | 0.081 (3) | 0.012 (2) | 0.038 (2) | 0.038 (3) |
C24 | 0.0387 (16) | 0.0498 (17) | 0.0567 (19) | 0.0062 (13) | 0.0012 (15) | 0.0023 (16) |
C25 | 0.067 (2) | 0.077 (3) | 0.072 (2) | 0.024 (2) | −0.003 (2) | −0.007 (2) |
C26 | 0.0308 (14) | 0.0571 (18) | 0.0479 (18) | 0.0103 (13) | 0.0022 (14) | 0.0090 (16) |
C27 | 0.0482 (19) | 0.073 (2) | 0.057 (2) | 0.0023 (17) | −0.0059 (17) | 0.0125 (19) |
C28 | 0.055 (2) | 0.080 (3) | 0.091 (3) | −0.0040 (18) | −0.025 (2) | 0.013 (2) |
C29 | 0.082 (3) | 0.099 (3) | 0.084 (3) | 0.009 (3) | −0.044 (3) | 0.000 (3) |
C30 | 0.089 (3) | 0.106 (3) | 0.057 (2) | 0.011 (3) | −0.021 (2) | 0.018 (2) |
C31 | 0.057 (2) | 0.079 (2) | 0.054 (2) | 0.0035 (17) | −0.0029 (18) | 0.0169 (19) |
O1—C19 | 1.354 (3) | C13—H13A | 0.9300 |
O1—H1 | 0.93 (4) | C14—C15 | 1.392 (4) |
N1—C13 | 1.272 (4) | C14—C19 | 1.405 (4) |
N1—C1 | 1.443 (3) | C15—C16 | 1.381 (4) |
C1—C6 | 1.398 (4) | C15—H15A | 0.9300 |
C1—C2 | 1.400 (4) | C16—C17 | 1.398 (4) |
C2—C3 | 1.395 (4) | C16—C20 | 1.526 (4) |
C2—C10 | 1.516 (4) | C17—C18 | 1.387 (4) |
C3—C4 | 1.372 (5) | C17—H17A | 0.9300 |
C3—H3A | 0.9300 | C18—C19 | 1.389 (4) |
C4—C5 | 1.376 (5) | C18—C24 | 1.525 (4) |
C4—H4A | 0.9300 | C20—C22 | 1.527 (5) |
C5—C6 | 1.392 (4) | C20—C23 | 1.527 (5) |
C5—H5A | 0.9300 | C20—C21 | 1.532 (5) |
C6—C7 | 1.520 (5) | C21—H21A | 0.9600 |
C7—C8 | 1.480 (7) | C21—H21B | 0.9600 |
C7—C9 | 1.535 (7) | C21—H21C | 0.9600 |
C7—H7A | 0.9800 | C22—H22A | 0.9600 |
C8—H8A | 0.9600 | C22—H22B | 0.9600 |
C8—H8B | 0.9600 | C22—H22C | 0.9600 |
C8—H8C | 0.9600 | C23—H23A | 0.9600 |
C9—H9A | 0.9600 | C23—H23B | 0.9600 |
C9—H9B | 0.9600 | C23—H23C | 0.9600 |
C9—H9C | 0.9600 | C24—C26 | 1.519 (5) |
C8'—H8'A | 0.9600 | C24—C25 | 1.528 (5) |
C8'—H8'B | 0.9600 | C24—H24A | 0.9800 |
C8'—H8'C | 0.9600 | C25—H25A | 0.9600 |
C9'—H9'A | 0.9600 | C25—H25B | 0.9600 |
C9'—H9'B | 0.9600 | C25—H25C | 0.9600 |
C9'—H9'C | 0.9600 | C26—C31 | 1.375 (5) |
C10—C11 | 1.509 (5) | C26—C27 | 1.385 (4) |
C10—C12 | 1.517 (5) | C27—C28 | 1.381 (5) |
C10—H10A | 0.9800 | C27—H27A | 0.9300 |
C11—H11A | 0.9600 | C28—C29 | 1.366 (6) |
C11—H11B | 0.9600 | C28—H28A | 0.9300 |
C11—H11C | 0.9600 | C29—C30 | 1.373 (6) |
C12—H12A | 0.9600 | C29—H29A | 0.9300 |
C12—H12B | 0.9600 | C30—C31 | 1.383 (6) |
C12—H12C | 0.9600 | C30—H30A | 0.9300 |
C13—C14 | 1.458 (4) | C31—H31A | 0.9300 |
C19—O1—H1 | 108 (2) | C16—C15—H15A | 118.6 |
C13—N1—C1 | 119.5 (2) | C14—C15—H15A | 118.6 |
C6—C1—C2 | 122.3 (3) | C15—C16—C17 | 116.0 (3) |
C6—C1—N1 | 120.6 (3) | C15—C16—C20 | 121.6 (3) |
C2—C1—N1 | 117.0 (3) | C17—C16—C20 | 122.4 (2) |
C3—C2—C1 | 117.5 (3) | C18—C17—C16 | 123.7 (3) |
C3—C2—C10 | 120.6 (3) | C18—C17—H17A | 118.1 |
C1—C2—C10 | 121.8 (2) | C16—C17—H17A | 118.1 |
C4—C3—C2 | 121.2 (3) | C17—C18—C19 | 118.4 (2) |
C4—C3—H3A | 119.4 | C17—C18—C24 | 122.1 (3) |
C2—C3—H3A | 119.4 | C19—C18—C24 | 119.5 (3) |
C3—C4—C5 | 120.1 (3) | O1—C19—C18 | 118.8 (2) |
C3—C4—H4A | 120.0 | O1—C19—C14 | 121.2 (2) |
C5—C4—H4A | 120.0 | C18—C19—C14 | 120.0 (2) |
C4—C5—C6 | 121.6 (3) | C16—C20—C22 | 108.8 (3) |
C4—C5—H5A | 119.2 | C16—C20—C23 | 112.7 (3) |
C6—C5—H5A | 119.2 | C22—C20—C23 | 109.5 (3) |
C5—C6—C1 | 117.3 (3) | C16—C20—C21 | 110.4 (3) |
C5—C6—C7 | 120.6 (3) | C22—C20—C21 | 108.0 (3) |
C1—C6—C7 | 122.1 (3) | C23—C20—C21 | 107.4 (3) |
C8—C7—C6 | 111.5 (5) | C20—C21—H21A | 109.5 |
C8—C7—C9 | 108.9 (7) | C20—C21—H21B | 109.5 |
C6—C7—C9 | 113.9 (4) | H21A—C21—H21B | 109.5 |
C8—C7—H7A | 107.4 | C20—C21—H21C | 109.5 |
C6—C7—H7A | 107.4 | H21A—C21—H21C | 109.5 |
C9—C7—H7A | 107.4 | H21B—C21—H21C | 109.5 |
C7—C8—H8A | 109.5 | C20—C22—H22A | 109.5 |
C7—C8—H8B | 109.5 | C20—C22—H22B | 109.5 |
H8A—C8—H8B | 109.5 | H22A—C22—H22B | 109.5 |
C7—C8—H8C | 109.5 | C20—C22—H22C | 109.5 |
H8A—C8—H8C | 109.5 | H22A—C22—H22C | 109.5 |
H8B—C8—H8C | 109.5 | H22B—C22—H22C | 109.5 |
C7—C9—H9A | 109.5 | C20—C23—H23A | 109.5 |
C7—C9—H9B | 109.5 | C20—C23—H23B | 109.5 |
H9A—C9—H9B | 109.5 | H23A—C23—H23B | 109.5 |
C7—C9—H9C | 109.5 | C20—C23—H23C | 109.5 |
H9A—C9—H9C | 109.5 | H23A—C23—H23C | 109.5 |
H9B—C9—H9C | 109.5 | H23B—C23—H23C | 109.5 |
H8'A—C8'—H8'B | 109.5 | C26—C24—C18 | 110.2 (2) |
H8'A—C8'—H8'C | 109.5 | C26—C24—C25 | 112.6 (3) |
H8'B—C8'—H8'C | 109.5 | C18—C24—C25 | 113.4 (3) |
H9'A—C9'—H9'B | 109.5 | C26—C24—H24A | 106.7 |
H9'A—C9'—H9'C | 109.5 | C18—C24—H24A | 106.7 |
H9'B—C9'—H9'C | 109.5 | C25—C24—H24A | 106.7 |
C11—C10—C2 | 113.6 (3) | C24—C25—H25A | 109.5 |
C11—C10—C12 | 111.4 (3) | C24—C25—H25B | 109.5 |
C2—C10—C12 | 109.3 (3) | H25A—C25—H25B | 109.5 |
C11—C10—H10A | 107.4 | C24—C25—H25C | 109.5 |
C2—C10—H10A | 107.4 | H25A—C25—H25C | 109.5 |
C12—C10—H10A | 107.4 | H25B—C25—H25C | 109.5 |
C10—C11—H11A | 109.5 | C31—C26—C27 | 117.7 (3) |
C10—C11—H11B | 109.5 | C31—C26—C24 | 120.9 (3) |
H11A—C11—H11B | 109.5 | C27—C26—C24 | 121.4 (3) |
C10—C11—H11C | 109.5 | C28—C27—C26 | 121.7 (3) |
H11A—C11—H11C | 109.5 | C28—C27—H27A | 119.1 |
H11B—C11—H11C | 109.5 | C26—C27—H27A | 119.1 |
C10—C12—H12A | 109.5 | C29—C28—C27 | 119.4 (4) |
C10—C12—H12B | 109.5 | C29—C28—H28A | 120.3 |
H12A—C12—H12B | 109.5 | C27—C28—H28A | 120.3 |
C10—C12—H12C | 109.5 | C28—C29—C30 | 120.0 (4) |
H12A—C12—H12C | 109.5 | C28—C29—H29A | 120.0 |
H12B—C12—H12C | 109.5 | C30—C29—H29A | 120.0 |
N1—C13—C14 | 122.7 (3) | C29—C30—C31 | 120.1 (4) |
N1—C13—H13A | 118.6 | C29—C30—H30A | 120.0 |
C14—C13—H13A | 118.6 | C31—C30—H30A | 120.0 |
C15—C14—C19 | 119.0 (2) | C26—C31—C30 | 121.1 (4) |
C15—C14—C13 | 119.5 (2) | C26—C31—H31A | 119.5 |
C19—C14—C13 | 121.4 (2) | C30—C31—H31A | 119.5 |
C16—C15—C14 | 122.9 (3) | ||
C13—N1—C1—C6 | −87.7 (3) | C16—C17—C18—C19 | 0.9 (4) |
C13—N1—C1—C2 | 96.7 (3) | C16—C17—C18—C24 | −177.1 (3) |
C6—C1—C2—C3 | 0.5 (4) | C17—C18—C19—O1 | 179.0 (2) |
N1—C1—C2—C3 | 176.1 (3) | C24—C18—C19—O1 | −3.0 (4) |
C6—C1—C2—C10 | −176.7 (3) | C17—C18—C19—C14 | −0.7 (4) |
N1—C1—C2—C10 | −1.2 (4) | C24—C18—C19—C14 | 177.3 (3) |
C1—C2—C3—C4 | 0.4 (5) | C15—C14—C19—O1 | 179.9 (2) |
C10—C2—C3—C4 | 177.8 (3) | C13—C14—C19—O1 | −3.3 (4) |
C2—C3—C4—C5 | −0.1 (6) | C15—C14—C19—C18 | −0.4 (4) |
C3—C4—C5—C6 | −1.3 (6) | C13—C14—C19—C18 | 176.4 (3) |
C4—C5—C6—C1 | 2.2 (5) | C15—C16—C20—C22 | 69.1 (4) |
C4—C5—C6—C7 | −175.8 (3) | C17—C16—C20—C22 | −109.4 (3) |
C2—C1—C6—C5 | −1.8 (4) | C15—C16—C20—C23 | −169.3 (3) |
N1—C1—C6—C5 | −177.2 (3) | C17—C16—C20—C23 | 12.2 (4) |
C2—C1—C6—C7 | 176.2 (3) | C15—C16—C20—C21 | −49.2 (4) |
N1—C1—C6—C7 | 0.8 (4) | C17—C16—C20—C21 | 132.3 (3) |
C5—C6—C7—C8 | 94.5 (6) | C17—C18—C24—C26 | 90.3 (3) |
C1—C6—C7—C8 | −83.4 (6) | C19—C18—C24—C26 | −87.6 (3) |
C5—C6—C7—C9 | −29.2 (7) | C17—C18—C24—C25 | −37.0 (4) |
C1—C6—C7—C9 | 152.9 (6) | C19—C18—C24—C25 | 145.1 (3) |
C3—C2—C10—C11 | 36.4 (4) | C18—C24—C26—C31 | 115.0 (3) |
C1—C2—C10—C11 | −146.4 (3) | C25—C24—C26—C31 | −117.3 (4) |
C3—C2—C10—C12 | −88.6 (4) | C18—C24—C26—C27 | −64.6 (4) |
C1—C2—C10—C12 | 88.6 (4) | C25—C24—C26—C27 | 63.1 (4) |
C1—N1—C13—C14 | −172.8 (3) | C31—C26—C27—C28 | −0.5 (5) |
N1—C13—C14—C15 | 178.5 (3) | C24—C26—C27—C28 | 179.2 (3) |
N1—C13—C14—C19 | 1.7 (4) | C26—C27—C28—C29 | 0.4 (6) |
C19—C14—C15—C16 | 1.4 (4) | C27—C28—C29—C30 | −0.3 (7) |
C13—C14—C15—C16 | −175.5 (3) | C28—C29—C30—C31 | 0.2 (7) |
C14—C15—C16—C17 | −1.2 (4) | C27—C26—C31—C30 | 0.4 (5) |
C14—C15—C16—C20 | −179.8 (3) | C24—C26—C31—C30 | −179.2 (3) |
C15—C16—C17—C18 | 0.1 (4) | C29—C30—C31—C26 | −0.3 (6) |
C20—C16—C17—C18 | 178.7 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.93 (4) | 1.79 (4) | 2.620 (3) | 147 (3) |
Experimental details
Crystal data | |
Chemical formula | C31H39NO |
Mr | 441.63 |
Crystal system, space group | Orthorhombic, Pca21 |
Temperature (K) | 294 |
a, b, c (Å) | 25.273 (4), 9.5496 (18), 11.115 (2) |
V (Å3) | 2682.6 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.24 × 0.20 × 0.16 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.974, 0.990 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13332, 2505, 1964 |
Rint | 0.039 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.105, 1.06 |
No. of reflections | 2505 |
No. of parameters | 319 |
No. of restraints | 41 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.13, −0.12 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1 | 0.93 (4) | 1.79 (4) | 2.620 (3) | 147 (3) |
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Late-metal catalysts bearing salicylaldiminato-type ligands play an important role in the catalytic oligomerization and polymerization of olefins (Ittel et al., 2000). Increasing the size of the imino substituent and the o-phenoxy substituent has a pronounced effect on the activity of the catalyst and the molecular weight of the polymer (Gibson et al., 2003). We have recently prepared a novel ligand, (I), and report its crystal structure here.
The molecular structure of (I) is shown in Fig. 1. In (I) the phenyl ring and the phenoxy ring form a dihedral angle of 75.18 (1)°, the phenylimino ring is nearly perpendicular to the phenoxy ring, with a dihedral angle of 81.51 (2)°. The dihedral angle between the phenyl and the phenylimino ring is 62.88 (1)°. Three C atoms of isopropyl attaching to the phenylimino ring are disordered in two locations with 55% and 45% probabilities. An intramolecular hydrogen bond is formed between the hydroxyl group and the N atom stabilizing the crystal structure.