Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807031832/fl2134sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807031832/fl2134Isup2.hkl |
CCDC reference: 657760
Key indicators
- Single-crystal X-ray study
- T = 292 K
- Mean (C-C) = 0.005 Å
- R factor = 0.059
- wR factor = 0.188
- Data-to-parameter ratio = 13.8
checkCIF/PLATON results
No syntax errors found
Alert level C WEIGH01_ALERT_1_C Extra text has been found in the _refine_ls_weighting_scheme field. This should be in the _refine_ls_weighting_details field. Weighting scheme given as calc w=1/[\s^2^(Fo^2^)+(0.1107P)^2^] where Weighting scheme identified as calc PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 47 Perc. PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A PUBL022_ALERT_1_A There is a mismatched ~ on line 167 C~28~H~21~NO~2~.C~2~H~5~O~H, indicates If you require a ~ then it should be escaped with a \, i.e. \~ Otherwise there must be a matching closing ~, e.g. C~2~H~4~
1 ALERT level A = Data missing that is essential or data in wrong format 0 ALERT level G = General alerts. Data that may be required is missing
The salen ligand, 3-((p-tolylimino)methyl)-di-1,1'-binaphthol was prepared by condensation of 3-carboxaldehyde-1,1'-binaphthol with p-toluidine, which was prepared in reported methods (Chin, J. et al., 2004).Crystals suitable for X-ray analysis were obtained by slow evaporation of a ethanol /methylene chloride (1:5) solution of the compound.
H2 was located in a difference Fourier map and refined with restraints on the O—H distance. The remaining H atoms were placed in calculated positions and refined in the riding-model approximation.
Copper and manganese complexes containing Schiff bases as ligands have potential interest in homogeneous catalysis(Raffaelli et al., 1998).In this paper, we present and X-ray crystallographic analysis of the title compound (I), as a continuation of our previous studies. The binol backbone indicates that it has potential as a ligand in asymmetric synthesis.
As shown in Fig. 1, an intramolecular O—H···N hydrogen bond forms a five–membered ring. Both hydroxyl group and the imino moiety provide potential sites for coordination with metal ions as a O/N heterotridenate ligand.
The compounds (I) are connected by O—H···O hydrogen bonds to the ethanol, Fig 2.
In the crystal structure there are close approaches between the ring systems in neighboring molecules, for example, C11–15, 20 and C11–15, 20 rings, C11–15, 20 and C15–20 rings, and C11–15, 20 and C22–27 rings, the corresponding distances between ring centroids are 3.875 Å, 3.956Å and 4.110 Å.
For background on the application of salen complexes to asymmetric catalysis see: Raffaelli et al. (1998); for synthesis see Chin et al. (2004).
Data collection: DIFRAC (Gabe & White, 1993); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Version 1.2; Bruno et al., 2002); software used to prepare material for publication: SHELXL97.
Fig. 1. A perspective view, with displacement ellipsoids drawn at the 30% propability level. | |
Fig. 2. Intermolecular hydrogen bonding in the crystal structure of (I). |
C28H21NO2·C2H6O | Z = 2 |
Mr = 449.53 | F(000) = 476 |
Triclinic, P1 | Dx = 1.250 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.540 (5) Å | Cell parameters from 24 reflections |
b = 10.740 (3) Å | θ = 4.8–9.1° |
c = 10.779 (3) Å | µ = 0.08 mm−1 |
α = 82.17 (2)° | T = 292 K |
β = 83.82 (3)° | Block, orange |
γ = 82.89 (3)° | 0.26 × 0.25 × 0.13 mm |
V = 1194.4 (8) Å3 |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.010 |
Radiation source: fine-focus sealed tube | θmax = 25.5°, θmin = 1.9° |
Graphite monochromator | h = −12→12 |
ω/2θ scans | k = −4→12 |
4426 measured reflections | l = −12→13 |
4391 independent reflections | 3 standard reflections every 300 reflections |
2054 reflections with I > 2σ(I) | intensity decay: 3.2% |
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)] = 0.059 | Hydrogen site location: mixed |
wR(F2) = 0.188 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.94 | w = 1/[\s^2^(Fo^2^) + (0.1107P)^2^] where P = (Fo^2^ + 2Fc^2^)/3 |
4391 reflections | (Δ/σ)max < 0.001 |
319 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
C28H21NO2·C2H6O | γ = 82.89 (3)° |
Mr = 449.53 | V = 1194.4 (8) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.540 (5) Å | Mo Kα radiation |
b = 10.740 (3) Å | µ = 0.08 mm−1 |
c = 10.779 (3) Å | T = 292 K |
α = 82.17 (2)° | 0.26 × 0.25 × 0.13 mm |
β = 83.82 (3)° |
Enraf–Nonius CAD-4 diffractometer | Rint = 0.010 |
4426 measured reflections | 3 standard reflections every 300 reflections |
4391 independent reflections | intensity decay: 3.2% |
2054 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.059 | 0 restraints |
wR(F2) = 0.188 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.94 | Δρmax = 0.21 e Å−3 |
4391 reflections | Δρmin = −0.24 e Å−3 |
319 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 | ||
O1 | 0.0738 (2) | 0.3272 (2) | 0.5630 (2) | 0.0734 (7) | |
H1 | 0.0534 | 0.3780 | 0.6139 | 0.110 (11)* | |
O2 | 0.0508 (2) | 0.27804 (19) | 0.2159 (2) | 0.0599 (6) | |
H2 | 0.007 (4) | 0.264 (4) | 0.164 (4) | 0.100 (15)* | |
N | −0.0886 (2) | 0.1489 (2) | 0.1058 (2) | 0.0507 (6) | |
C1 | 0.3334 (3) | 0.3271 (2) | 0.3103 (3) | 0.0466 (7) | |
C2 | 0.3843 (3) | 0.2626 (3) | 0.2077 (3) | 0.0569 (8) | |
H2A | 0.3479 | 0.1920 | 0.1929 | 0.073 (2)* | |
C3 | 0.4861 (3) | 0.3018 (3) | 0.1295 (3) | 0.0709 (10) | |
H3 | 0.5179 | 0.2577 | 0.0622 | 0.073 (2)* | |
C4 | 0.5433 (3) | 0.4069 (3) | 0.1490 (3) | 0.0729 (10) | |
H4 | 0.6120 | 0.4330 | 0.0942 | 0.073 (2)* | |
C5 | 0.4991 (3) | 0.4711 (3) | 0.2475 (3) | 0.0623 (8) | |
H5 | 0.5387 | 0.5404 | 0.2605 | 0.073 (2)* | |
C6 | 0.3942 (3) | 0.4345 (2) | 0.3307 (3) | 0.0489 (7) | |
C7 | 0.3423 (3) | 0.5013 (3) | 0.4312 (3) | 0.0567 (8) | |
H7 | 0.3812 | 0.5701 | 0.4465 | 0.073 (2)* | |
C8 | 0.2379 (3) | 0.4687 (3) | 0.5060 (3) | 0.0611 (8) | |
H8 | 0.2045 | 0.5163 | 0.5703 | 0.073 (2)* | |
C9 | 0.1779 (3) | 0.3613 (2) | 0.4873 (3) | 0.0510 (7) | |
C10 | 0.2273 (3) | 0.2907 (2) | 0.3919 (3) | 0.0454 (7) | |
C11 | 0.1714 (3) | 0.1708 (2) | 0.3783 (2) | 0.0451 (7) | |
C12 | 0.0883 (3) | 0.1695 (2) | 0.2894 (3) | 0.0455 (7) | |
C13 | 0.0378 (3) | 0.0548 (2) | 0.2726 (2) | 0.0445 (7) | |
C14 | 0.0729 (3) | −0.0547 (2) | 0.3489 (2) | 0.0450 (7) | |
H14 | 0.0388 | −0.1284 | 0.3400 | 0.073 (2)* | |
C15 | 0.1591 (3) | −0.0574 (2) | 0.4397 (2) | 0.0440 (7) | |
C16 | 0.1966 (3) | −0.1712 (3) | 0.5162 (3) | 0.0526 (8) | |
H16 | 0.1611 | −0.2444 | 0.5081 | 0.073 (2)* | |
C17 | 0.2839 (3) | −0.1750 (3) | 0.6016 (3) | 0.0620 (8) | |
H17 | 0.3086 | −0.2501 | 0.6513 | 0.073 (2)* | |
C18 | 0.3356 (3) | −0.0639 (3) | 0.6129 (3) | 0.0657 (9) | |
H18 | 0.3965 | −0.0669 | 0.6700 | 0.073 (2)* | |
C19 | 0.3007 (3) | 0.0483 (3) | 0.5442 (3) | 0.0567 (8) | |
H19 | 0.3362 | 0.1204 | 0.5562 | 0.073 (2)* | |
C20 | 0.2104 (3) | 0.0561 (2) | 0.4543 (2) | 0.0444 (7) | |
C21 | −0.0490 (3) | 0.0512 (3) | 0.1792 (3) | 0.0484 (7) | |
H21 | −0.0776 | −0.0258 | 0.1718 | 0.073 (2)* | |
C22 | −0.1786 (3) | 0.1411 (3) | 0.0189 (3) | 0.0482 (7) | |
C23 | −0.2544 (3) | 0.0420 (3) | 0.0260 (3) | 0.0579 (8) | |
H23 | −0.2474 | −0.0246 | 0.0906 | 0.073 (2)* | |
C24 | −0.3389 (3) | 0.0430 (3) | −0.0618 (3) | 0.0568 (8) | |
H24 | −0.3867 | −0.0250 | −0.0572 | 0.073 (2)* | |
C25 | −0.3554 (3) | 0.1417 (3) | −0.1573 (3) | 0.0567 (8) | |
C26 | −0.2799 (3) | 0.2399 (3) | −0.1640 (3) | 0.0606 (8) | |
H26 | −0.2877 | 0.3069 | −0.2282 | 0.073 (2)* | |
C27 | −0.1936 (3) | 0.2392 (3) | −0.0768 (3) | 0.0561 (8) | |
H27 | −0.1443 | 0.3062 | −0.0827 | 0.073 (2)* | |
C28 | −0.4529 (3) | 0.1425 (3) | −0.2510 (3) | 0.0725 (10) | |
H28A | −0.5307 | 0.1145 | −0.2076 | 0.172 (9)* | |
H28B | −0.4191 | 0.0868 | −0.3120 | 0.172 (9)* | |
H28C | −0.4708 | 0.2268 | −0.2927 | 0.172 (9)* | |
O3 | 0.0233 (2) | 0.4606 (2) | 0.7668 (2) | 0.0754 (7) | |
H3A | −0.0169 | 0.5313 | 0.7612 | 0.110 (11)* | |
C29 | 0.1223 (4) | 0.4550 (4) | 0.8508 (4) | 0.0950 (13) | |
H29A | 0.0844 | 0.4794 | 0.9312 | 0.170 (16)* | |
H29B | 0.1837 | 0.5136 | 0.8158 | 0.170 (16)* | |
C30 | 0.1883 (5) | 0.3249 (5) | 0.8689 (5) | 0.1227 (17) | |
H30A | 0.2597 | 0.3233 | 0.9177 | 0.172 (9)* | |
H30B | 0.2188 | 0.2983 | 0.7885 | 0.172 (9)* | |
H30C | 0.1294 | 0.2688 | 0.9124 | 0.172 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0815 (17) | 0.0628 (14) | 0.0813 (16) | −0.0284 (12) | 0.0206 (13) | −0.0314 (12) |
O2 | 0.0766 (16) | 0.0398 (11) | 0.0687 (14) | −0.0135 (10) | −0.0299 (12) | −0.0018 (10) |
N | 0.0520 (15) | 0.0505 (14) | 0.0535 (14) | −0.0095 (11) | −0.0157 (12) | −0.0093 (12) |
C1 | 0.0484 (17) | 0.0425 (15) | 0.0506 (16) | −0.0025 (13) | −0.0132 (14) | −0.0073 (13) |
C2 | 0.059 (2) | 0.0532 (17) | 0.0617 (19) | −0.0109 (15) | −0.0057 (16) | −0.0137 (15) |
C3 | 0.067 (2) | 0.076 (2) | 0.070 (2) | −0.0011 (18) | 0.0040 (19) | −0.0255 (18) |
C4 | 0.062 (2) | 0.073 (2) | 0.082 (2) | −0.0127 (18) | 0.0097 (18) | −0.009 (2) |
C5 | 0.064 (2) | 0.0551 (19) | 0.071 (2) | −0.0166 (16) | −0.0079 (18) | −0.0086 (16) |
C6 | 0.0522 (18) | 0.0390 (15) | 0.0577 (17) | −0.0076 (13) | −0.0130 (14) | −0.0054 (13) |
C7 | 0.066 (2) | 0.0492 (17) | 0.0615 (19) | −0.0230 (15) | −0.0092 (17) | −0.0112 (14) |
C8 | 0.078 (2) | 0.0469 (17) | 0.0623 (19) | −0.0144 (16) | −0.0024 (17) | −0.0166 (15) |
C9 | 0.0591 (19) | 0.0429 (15) | 0.0546 (17) | −0.0144 (14) | −0.0032 (15) | −0.0123 (14) |
C10 | 0.0442 (17) | 0.0424 (15) | 0.0528 (17) | −0.0098 (12) | −0.0124 (14) | −0.0063 (13) |
C11 | 0.0482 (17) | 0.0383 (15) | 0.0526 (16) | −0.0085 (12) | −0.0079 (14) | −0.0135 (13) |
C12 | 0.0491 (17) | 0.0358 (15) | 0.0532 (17) | −0.0065 (12) | −0.0074 (14) | −0.0073 (13) |
C13 | 0.0442 (16) | 0.0420 (15) | 0.0508 (16) | −0.0078 (12) | −0.0064 (13) | −0.0141 (13) |
C14 | 0.0471 (17) | 0.0368 (15) | 0.0542 (17) | −0.0097 (12) | −0.0012 (14) | −0.0150 (13) |
C15 | 0.0437 (17) | 0.0387 (15) | 0.0497 (16) | −0.0033 (12) | −0.0015 (13) | −0.0090 (12) |
C16 | 0.060 (2) | 0.0384 (15) | 0.0595 (18) | −0.0057 (13) | −0.0017 (16) | −0.0076 (13) |
C17 | 0.070 (2) | 0.0507 (18) | 0.062 (2) | 0.0003 (15) | −0.0131 (17) | 0.0014 (15) |
C18 | 0.070 (2) | 0.064 (2) | 0.067 (2) | −0.0052 (17) | −0.0264 (17) | −0.0092 (17) |
C19 | 0.061 (2) | 0.0501 (17) | 0.0634 (19) | −0.0105 (14) | −0.0183 (16) | −0.0095 (15) |
C20 | 0.0441 (17) | 0.0435 (15) | 0.0482 (16) | −0.0068 (12) | −0.0064 (13) | −0.0117 (12) |
C21 | 0.0450 (17) | 0.0456 (16) | 0.0598 (18) | −0.0108 (13) | −0.0067 (14) | −0.0182 (14) |
C22 | 0.0436 (17) | 0.0497 (16) | 0.0535 (17) | −0.0061 (13) | −0.0048 (14) | −0.0132 (14) |
C23 | 0.058 (2) | 0.0542 (18) | 0.0637 (19) | −0.0142 (15) | −0.0085 (16) | −0.0064 (15) |
C24 | 0.0517 (19) | 0.0571 (18) | 0.069 (2) | −0.0146 (14) | −0.0073 (16) | −0.0231 (16) |
C25 | 0.0490 (19) | 0.068 (2) | 0.0565 (18) | −0.0022 (15) | −0.0049 (15) | −0.0234 (16) |
C26 | 0.060 (2) | 0.064 (2) | 0.0589 (19) | −0.0088 (16) | −0.0124 (16) | −0.0061 (16) |
C27 | 0.056 (2) | 0.0501 (17) | 0.0644 (19) | −0.0127 (14) | −0.0061 (16) | −0.0082 (15) |
C28 | 0.055 (2) | 0.097 (3) | 0.075 (2) | −0.0125 (18) | −0.0226 (18) | −0.025 (2) |
O3 | 0.0790 (18) | 0.0612 (15) | 0.0881 (17) | −0.0015 (12) | −0.0025 (14) | −0.0261 (13) |
C29 | 0.095 (3) | 0.099 (3) | 0.097 (3) | −0.006 (3) | −0.022 (3) | −0.025 (2) |
C30 | 0.108 (4) | 0.110 (4) | 0.139 (4) | 0.014 (3) | −0.016 (3) | 0.005 (3) |
O1—C9 | 1.352 (3) | C15—C20 | 1.427 (3) |
O1—H1 | 0.8200 | C16—C17 | 1.364 (4) |
O2—C12 | 1.358 (3) | C16—H16 | 0.9300 |
O2—H2 | 0.80 (4) | C17—C18 | 1.397 (4) |
N—C21 | 1.280 (3) | C17—H17 | 0.9300 |
N—C22 | 1.420 (4) | C18—C19 | 1.357 (4) |
C1—C2 | 1.407 (4) | C18—H18 | 0.9300 |
C1—C10 | 1.408 (4) | C19—C20 | 1.417 (4) |
C1—C6 | 1.439 (4) | C19—H19 | 0.9300 |
C2—C3 | 1.363 (4) | C21—H21 | 0.9300 |
C2—H2A | 0.9300 | C22—C27 | 1.377 (4) |
C3—C4 | 1.394 (5) | C22—C23 | 1.397 (4) |
C3—H3 | 0.9300 | C23—C24 | 1.366 (4) |
C4—C5 | 1.354 (4) | C23—H23 | 0.9300 |
C4—H4 | 0.9300 | C24—C25 | 1.382 (4) |
C5—C6 | 1.407 (4) | C24—H24 | 0.9300 |
C5—H5 | 0.9300 | C25—C26 | 1.387 (4) |
C6—C7 | 1.405 (4) | C25—C28 | 1.515 (4) |
C7—C8 | 1.346 (4) | C26—C27 | 1.375 (4) |
C7—H7 | 0.9300 | C26—H26 | 0.9300 |
C8—C9 | 1.429 (4) | C27—H27 | 0.9300 |
C8—H8 | 0.9300 | C28—H28A | 0.9600 |
C9—C10 | 1.379 (4) | C28—H28B | 0.9600 |
C10—C11 | 1.512 (3) | C28—H28C | 0.9600 |
C11—C12 | 1.368 (4) | O3—C29 | 1.444 (4) |
C11—C20 | 1.425 (4) | O3—H3A | 0.8200 |
C12—C13 | 1.441 (3) | C29—C30 | 1.480 (6) |
C13—C14 | 1.375 (4) | C29—H29A | 0.9700 |
C13—C21 | 1.439 (4) | C29—H29B | 0.9700 |
C14—C15 | 1.400 (4) | C30—H30A | 0.9600 |
C14—H14 | 0.9300 | C30—H30B | 0.9600 |
C15—C16 | 1.417 (4) | C30—H30C | 0.9600 |
C9—O1—H1 | 109.5 | C16—C17—H17 | 120.7 |
C12—O2—H2 | 111 (3) | C18—C17—H17 | 120.7 |
C21—N—C22 | 120.8 (2) | C19—C18—C17 | 122.7 (3) |
C2—C1—C10 | 122.8 (3) | C19—C18—H18 | 118.6 |
C2—C1—C6 | 117.5 (3) | C17—C18—H18 | 118.6 |
C10—C1—C6 | 119.7 (2) | C18—C19—C20 | 120.3 (3) |
C3—C2—C1 | 121.1 (3) | C18—C19—H19 | 119.9 |
C3—C2—H2A | 119.4 | C20—C19—H19 | 119.9 |
C1—C2—H2A | 119.4 | C19—C20—C11 | 122.8 (2) |
C2—C3—C4 | 121.0 (3) | C19—C20—C15 | 117.6 (3) |
C2—C3—H3 | 119.5 | C11—C20—C15 | 119.6 (2) |
C4—C3—H3 | 119.5 | N—C21—C13 | 123.0 (3) |
C5—C4—C3 | 120.2 (3) | N—C21—H21 | 118.5 |
C5—C4—H4 | 119.9 | C13—C21—H21 | 118.5 |
C3—C4—H4 | 119.9 | C27—C22—C23 | 118.2 (3) |
C4—C5—C6 | 120.9 (3) | C27—C22—N | 117.6 (3) |
C4—C5—H5 | 119.5 | C23—C22—N | 124.2 (3) |
C6—C5—H5 | 119.5 | C24—C23—C22 | 120.1 (3) |
C7—C6—C5 | 122.8 (3) | C24—C23—H23 | 120.0 |
C7—C6—C1 | 117.9 (3) | C22—C23—H23 | 120.0 |
C5—C6—C1 | 119.3 (3) | C23—C24—C25 | 122.0 (3) |
C8—C7—C6 | 122.0 (3) | C23—C24—H24 | 119.0 |
C8—C7—H7 | 119.0 | C25—C24—H24 | 119.0 |
C6—C7—H7 | 119.0 | C24—C25—C26 | 117.7 (3) |
C7—C8—C9 | 120.4 (3) | C24—C25—C28 | 121.0 (3) |
C7—C8—H8 | 119.8 | C26—C25—C28 | 121.3 (3) |
C9—C8—H8 | 119.8 | C27—C26—C25 | 120.7 (3) |
O1—C9—C10 | 119.6 (2) | C27—C26—H26 | 119.7 |
O1—C9—C8 | 120.7 (3) | C25—C26—H26 | 119.7 |
C10—C9—C8 | 119.8 (3) | C26—C27—C22 | 121.3 (3) |
C9—C10—C1 | 120.1 (2) | C26—C27—H27 | 119.3 |
C9—C10—C11 | 120.1 (3) | C22—C27—H27 | 119.3 |
C1—C10—C11 | 119.7 (2) | C25—C28—H28A | 109.5 |
C12—C11—C20 | 119.4 (2) | C25—C28—H28B | 109.5 |
C12—C11—C10 | 120.8 (2) | H28A—C28—H28B | 109.5 |
C20—C11—C10 | 119.8 (2) | C25—C28—H28C | 109.5 |
O2—C12—C11 | 119.9 (2) | H28A—C28—H28C | 109.5 |
O2—C12—C13 | 118.7 (2) | H28B—C28—H28C | 109.5 |
C11—C12—C13 | 121.3 (2) | C29—O3—H3A | 109.5 |
C14—C13—C21 | 118.8 (2) | O3—C29—C30 | 109.6 (4) |
C14—C13—C12 | 119.0 (2) | O3—C29—H29A | 109.7 |
C21—C13—C12 | 122.2 (3) | C30—C29—H29A | 109.7 |
C13—C14—C15 | 121.3 (2) | O3—C29—H29B | 109.7 |
C13—C14—H14 | 119.3 | C30—C29—H29B | 109.7 |
C15—C14—H14 | 119.3 | H29A—C29—H29B | 108.2 |
C14—C15—C16 | 120.9 (2) | C29—C30—H30A | 109.5 |
C14—C15—C20 | 119.4 (2) | C29—C30—H30B | 109.5 |
C16—C15—C20 | 119.7 (3) | H30A—C30—H30B | 109.5 |
C17—C16—C15 | 121.0 (3) | C29—C30—H30C | 109.5 |
C17—C16—H16 | 119.5 | H30A—C30—H30C | 109.5 |
C15—C16—H16 | 119.5 | H30B—C30—H30C | 109.5 |
C16—C17—C18 | 118.7 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O3 | 0.82 | 1.95 | 2.753 (3) | 164 |
O2—H2···N | 0.80 (4) | 1.90 (4) | 2.612 (3) | 148 (4) |
O3—H3A···O2i | 0.82 | 2.08 | 2.844 (3) | 155 |
Symmetry code: (i) −x, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C28H21NO2·C2H6O |
Mr | 449.53 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 292 |
a, b, c (Å) | 10.540 (5), 10.740 (3), 10.779 (3) |
α, β, γ (°) | 82.17 (2), 83.82 (3), 82.89 (3) |
V (Å3) | 1194.4 (8) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.26 × 0.25 × 0.13 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4426, 4391, 2054 |
Rint | 0.010 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.059, 0.188, 0.94 |
No. of reflections | 4391 |
No. of parameters | 319 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.21, −0.24 |
Computer programs: DIFRAC (Gabe & White, 1993), DIFRAC, NRCVAX (Gabe et al., 1989), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Version 1.2; Bruno et al., 2002), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O3 | 0.82 | 1.95 | 2.753 (3) | 164.4 |
O2—H2···N | 0.80 (4) | 1.90 (4) | 2.612 (3) | 148 (4) |
O3—H3A···O2i | 0.82 | 2.08 | 2.844 (3) | 155.4 |
Symmetry code: (i) −x, −y+1, −z+1. |
Copper and manganese complexes containing Schiff bases as ligands have potential interest in homogeneous catalysis(Raffaelli et al., 1998).In this paper, we present and X-ray crystallographic analysis of the title compound (I), as a continuation of our previous studies. The binol backbone indicates that it has potential as a ligand in asymmetric synthesis.
As shown in Fig. 1, an intramolecular O—H···N hydrogen bond forms a five–membered ring. Both hydroxyl group and the imino moiety provide potential sites for coordination with metal ions as a O/N heterotridenate ligand.
The compounds (I) are connected by O—H···O hydrogen bonds to the ethanol, Fig 2.
In the crystal structure there are close approaches between the ring systems in neighboring molecules, for example, C11–15, 20 and C11–15, 20 rings, C11–15, 20 and C15–20 rings, and C11–15, 20 and C22–27 rings, the corresponding distances between ring centroids are 3.875 Å, 3.956Å and 4.110 Å.