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Acta Cryst. (2008). E64, o743    [ doi:10.1107/S1600536808007204 ]

(E)-4-tert-Butyl-2-(2,6-diisopropylphenyliminomethyl)-6-(morpholinomethyl)phenol

Z. Zhu, J. Cui and M. Zhang

Abstract top

In the molecule of the title compound, C28H40N2O2, the tert-butyl group is disordered over two positions; site-occupation factors were kept fixed at 0.5. The morpholine ring has a chair conformation. Intramolecular O-H...N hydrogen bonding results in the formation of a planar six-membered ring, which is oriented at a dihedral angle of 0.70 (3)° with respect to the adjacent aromatic ring. The dihedral angle between the benzene rings is 67.66 (3)°.

Comment top

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)°.

Related literature top

For general background, see: Younkin et al. (2000); Gibson & Spitzmesser (2003). For ring puckering parameters, see: Cremer & Pople (1975).

Experimental top

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)

Refinement top

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.

Computing details top

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).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 35% probability level.
(E)-4-tert-Butyl-2-(2,6-diisopropylphenyliminomethyl)-6-(morpholinomethyl)phenol top
Crystal data top
C28H40N2O2Dx = 1.106 Mg m−3
Mr = 436.62Melting point: 364 K
Orthorhombic, Pna21Mo Kα radiation
λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 5337 reflections
a = 10.086 (2) Åθ = 1.9–29.7º
b = 20.394 (4) ŵ = 0.07 mm−1
c = 12.750 (3) ÅT = 113 (2) K
V = 2622.8 (10) Å3Block, yellow
Z = 40.12 × 0.10 × 0.06 mm
F000 = 952
Data collection top
Rigaku Saturn
diffractometer		4314 reflections with I > 2σ(I)
Monochromator: confocalRint = 0.040
T = 294(2) Kθmax = 25.0º
ω scansθmin = 2.3º
Absorption correction: multi-scan
(Blessing, 1995)		h = −12→11
Tmin = 0.992, Tmax = 0.996k = −24→24
25483 measured reflectionsl = −15→15
4618 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-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 = 1.04Δρmax = 0.18 e Å−3
4618 reflectionsΔρmin = −0.13 e Å−3
318 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0157 (15)
Secondary atom site location: difference Fourier map
Crystal data top
C28H40N2O2V = 2622.8 (10) Å3
Mr = 436.62Z = 4
Orthorhombic, Pna21Mo Kα
a = 10.086 (2) ŵ = 0.07 mm−1
b = 20.394 (4) ÅT = 113 (2) K
c = 12.750 (3) Å0.12 × 0.10 × 0.06 mm
Data collection top
Rigaku Saturn
diffractometer		4618 independent reflections
Absorption correction: multi-scan
(Blessing, 1995)		4314 reflections with I > 2σ(I)
Tmin = 0.992, Tmax = 0.996Rint = 0.040
25483 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.095Δρmax = 0.18 e Å−3
S = 1.04Δρmin = −0.13 e Å−3
4618 reflectionsAbsolute structure: ?
318 parametersFlack parameter: ?
? restraintsRogers parameter: ?
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.66312 (13)0.02738 (7)0.58337 (11)0.0474 (4)
O20.44036 (11)0.16255 (6)1.01270 (9)0.0279 (3)
H20.43030.19191.05590.042*
N10.47500 (13)0.04647 (6)0.74844 (11)0.0265 (3)
N20.32848 (13)0.25917 (7)1.10594 (11)0.0280 (3)
C10.53145 (19)0.10072 (9)0.68955 (16)0.0403 (5)
H1A0.61010.11680.72510.048*
H1B0.46780.13630.68570.048*
C20.5673 (2)0.07857 (11)0.58034 (18)0.0527 (6)
H2A0.48830.06320.54470.063*
H2B0.60250.11540.54100.063*
C30.6091 (2)−0.02659 (9)0.63968 (16)0.0406 (5)
H3A0.6740−0.06160.64270.049*
H3B0.5317−0.04300.60280.049*
C40.57015 (19)−0.00743 (9)0.74948 (15)0.0355 (4)
H4A0.5314−0.04490.78480.043*
H4B0.64850.00570.78820.043*
C50.44409 (19)0.06580 (9)0.85631 (14)0.0352 (4)
H5A0.52350.08340.88870.042*
H5B0.41810.02710.89560.042*
C60.33465 (16)0.11632 (8)0.86387 (13)0.0262 (4)
C70.33721 (15)0.16278 (8)0.94452 (12)0.0234 (3)
C80.23469 (15)0.20886 (8)0.95331 (13)0.0234 (3)
C90.12971 (16)0.20779 (7)0.88116 (13)0.0247 (3)
H9A0.06170.23830.88790.030*
C100.12458 (15)0.16266 (7)0.80036 (13)0.0254 (4)
C110.22915 (16)0.11738 (8)0.79479 (13)0.0260 (4)
H11A0.22730.08630.74150.031*
C120.01307 (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−0.01290.07790.62850.106*0.50
H13B−0.13480.09190.70150.106*0.50
H13C−0.00490.06170.74850.106*0.50
C140.0691 (10)0.1924 (4)0.6171 (6)0.061 (2)0.50
H14A0.10410.23500.63340.092*0.50
H14B−0.00060.19660.56630.092*0.50
H14C0.13840.16540.58890.092*0.50
C15−0.1030 (10)0.2032 (6)0.7539 (9)0.0307 (19)0.50
H15A−0.07860.24860.74790.046*0.50
H15B−0.12470.19350.82560.046*0.50
H15C−0.17850.19460.71020.046*0.50
C13'−0.0535 (11)0.0920 (4)0.7330 (8)0.049 (2)0.50
H13D−0.07960.08650.80490.074*0.50
H13E0.00820.05820.71420.074*0.50
H13F−0.13030.08920.68880.074*0.50
C14'0.0708 (11)0.1619 (4)0.6092 (6)0.063 (2)0.50
H14D0.11360.20330.59770.095*0.50
H14E0.00100.15620.55880.095*0.50
H14F0.13440.12710.60150.095*0.50
C15'−0.0942 (12)0.2112 (6)0.7301 (10)0.046 (3)0.50
H15D−0.05630.25410.72200.069*0.50
H15E−0.13400.20770.79820.069*0.50
H15F−0.16050.20440.67720.069*0.50
C160.23491 (16)0.25686 (8)1.03797 (13)0.0264 (4)
H16A0.16530.28661.04280.032*
C170.32130 (16)0.30595 (9)1.18948 (13)0.0288 (4)
C180.30559 (17)0.28018 (9)1.29173 (15)0.0327 (4)
C190.29501 (18)0.32502 (10)1.37352 (15)0.0379 (4)
H19A0.28150.30961.44130.045*
C200.3040 (2)0.39149 (10)1.35681 (15)0.0409 (5)
H20A0.29460.42051.41260.049*
C210.3271 (2)0.41500 (9)1.25706 (16)0.0400 (5)
H21A0.33560.46001.24700.048*
C220.33791 (17)0.37310 (9)1.17069 (15)0.0331 (4)
C230.3753 (2)0.40061 (9)1.06383 (15)0.0389 (5)
H23A0.36780.36501.01260.047*
C240.5192 (2)0.42388 (10)1.06373 (17)0.0443 (5)
H24A0.57600.38851.08510.066*
H24B0.52880.45991.11160.066*
H24C0.54330.43780.99440.066*
C250.2825 (2)0.45530 (12)1.0295 (2)0.0597 (6)
H25A0.19270.43971.03040.090*
H25B0.30520.46900.95970.090*
H25C0.29100.49181.07660.090*
C260.29776 (18)0.20684 (9)1.30904 (15)0.0373 (4)
H26A0.34230.18581.24960.045*
C270.1547 (2)0.18351 (11)1.3088 (2)0.0601 (6)
H27A0.11200.19781.24550.090*
H27B0.10920.20151.36830.090*
H27C0.15270.13651.31230.090*
C280.3684 (2)0.18417 (11)1.40882 (18)0.0525 (6)
H28A0.45880.19881.40750.079*
H28B0.36620.13721.41260.079*
H28C0.32450.20231.46900.079*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0416 (8)0.0574 (9)0.0433 (8)0.0162 (7)0.0116 (7)−0.0014 (7)
O20.0244 (6)0.0340 (7)0.0254 (6)0.0025 (5)−0.0045 (5)−0.0040 (5)
N10.0278 (7)0.0262 (7)0.0254 (7)0.0053 (6)0.0026 (6)−0.0005 (6)
N20.0264 (7)0.0319 (7)0.0259 (7)−0.0017 (6)−0.0010 (6)−0.0038 (6)
C10.0386 (10)0.0301 (9)0.0523 (13)0.0022 (8)0.0144 (10)0.0011 (8)
C20.0518 (12)0.0587 (13)0.0476 (13)0.0186 (10)0.0214 (11)0.0139 (11)
C30.0388 (10)0.0409 (10)0.0421 (11)0.0123 (8)−0.0039 (9)−0.0128 (9)
C40.0370 (9)0.0323 (9)0.0373 (10)0.0112 (8)−0.0018 (8)−0.0023 (8)
C50.0361 (10)0.0428 (10)0.0267 (9)0.0127 (8)−0.0016 (8)−0.0039 (8)
C60.0252 (8)0.0300 (8)0.0233 (8)0.0032 (6)0.0026 (7)−0.0004 (7)
C70.0224 (8)0.0275 (8)0.0204 (8)−0.0040 (6)−0.0003 (7)0.0030 (6)
C80.0227 (8)0.0241 (8)0.0235 (8)−0.0035 (6)0.0021 (7)0.0003 (6)
C90.0218 (8)0.0250 (8)0.0271 (9)0.0006 (6)0.0011 (7)−0.0020 (7)
C100.0236 (8)0.0291 (8)0.0234 (8)−0.0026 (6)0.0020 (7)−0.0013 (7)
C110.0296 (9)0.0257 (8)0.0227 (8)−0.0010 (6)0.0002 (7)−0.0034 (7)
C120.0269 (8)0.0373 (9)0.0281 (9)0.0023 (7)−0.0035 (7)−0.0084 (7)
C130.069 (5)0.051 (4)0.092 (7)0.011 (3)−0.032 (5)−0.040 (4)
C140.042 (3)0.118 (6)0.024 (3)0.011 (4)−0.008 (2)0.005 (3)
C150.031 (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)
C160.0256 (8)0.0252 (8)0.0285 (9)−0.0029 (6)0.0005 (7)−0.0022 (7)
C170.0242 (8)0.0360 (9)0.0261 (9)−0.0023 (7)−0.0027 (7)−0.0071 (7)
C180.0262 (9)0.0412 (10)0.0306 (10)−0.0007 (7)−0.0020 (8)−0.0046 (8)
C190.0355 (9)0.0514 (11)0.0267 (9)−0.0003 (8)0.0009 (8)−0.0082 (9)
C200.0445 (11)0.0454 (11)0.0330 (11)−0.0009 (9)0.0032 (9)−0.0143 (9)
C210.0484 (11)0.0324 (9)0.0392 (11)−0.0010 (8)−0.0012 (9)−0.0095 (8)
C220.0349 (9)0.0350 (9)0.0295 (9)−0.0026 (7)−0.0029 (8)−0.0047 (7)
C230.0489 (11)0.0355 (10)0.0323 (10)−0.0052 (8)−0.0032 (9)−0.0072 (8)
C240.0429 (11)0.0461 (11)0.0440 (11)0.0007 (9)0.0053 (10)−0.0051 (9)
C250.0538 (13)0.0767 (16)0.0485 (13)0.0090 (12)−0.0107 (11)0.0142 (12)
C260.0377 (10)0.0422 (10)0.0319 (10)0.0010 (8)0.0023 (9)−0.0007 (9)
C270.0497 (13)0.0569 (13)0.0738 (17)−0.0160 (11)−0.0136 (13)0.0043 (13)
C280.0514 (12)0.0545 (13)0.0516 (13)−0.0024 (10)−0.0053 (11)0.0130 (11)
Geometric parameters (Å, °) top
O1—C31.423 (3)C14—H14C0.9600
O1—C21.423 (2)C15—H15A0.9600
O2—C71.3558 (19)C15—H15B0.9600
O2—H20.8200C15—H15C0.9600
N1—C11.453 (2)C13'—H13D0.9600
N1—C41.459 (2)C13'—H13E0.9600
N1—C51.464 (2)C13'—H13F0.9600
N2—C161.282 (2)C14'—H14D0.9600
N2—C171.432 (2)C14'—H14E0.9600
C1—C21.508 (3)C14'—H14F0.9600
C1—H1A0.9700C15'—H15D0.9600
C1—H1B0.9700C15'—H15E0.9600
C2—H2A0.9700C15'—H15F0.9600
C2—H2B0.9700C16—H16A0.9300
C3—C41.506 (3)C17—C221.400 (3)
C3—H3A0.9700C17—C181.415 (3)
C3—H3B0.9700C18—C191.391 (3)
C4—H4A0.9700C18—C261.514 (3)
C4—H4B0.9700C19—C201.375 (3)
C5—C61.513 (2)C19—H19A0.9300
C5—H5A0.9700C20—C211.379 (3)
C5—H5B0.9700C20—H20A0.9300
C6—C111.382 (2)C21—C221.398 (3)
C6—C71.398 (2)C21—H21A0.9300
C7—C81.402 (2)C22—C231.521 (3)
C8—C91.403 (2)C23—C251.521 (3)
C8—C161.457 (2)C23—C241.527 (3)
C9—C101.382 (2)C23—H23A0.9800
C9—H9A0.9300C24—H24A0.9600
C10—C111.404 (2)C24—H24B0.9600
C10—C121.531 (2)C24—H24C0.9600
C11—H11A0.9300C25—H25A0.9600
C12—C15'1.508 (8)C25—H25B0.9600
C12—C14'1.517 (7)C25—H25C0.9600
C12—C131.522 (8)C26—C271.519 (3)
C12—C151.530 (7)C26—C281.530 (3)
C12—C13'1.554 (7)C26—H26A0.9800
C12—C141.561 (7)C27—H27A0.9600
C13—H13A0.9600C27—H27B0.9600
C13—H13B0.9600C27—H27C0.9600
C13—H13C0.9600C28—H28A0.9600
C14—H14A0.9600C28—H28B0.9600
C14—H14B0.9600C28—H28C0.9600
C3—O1—C2108.71 (14)H14B—C14—H14C109.5
C7—O2—H2109.5C12—C15—H15A109.5
C1—N1—C4108.69 (14)C12—C15—H15B109.5
C1—N1—C5111.33 (14)H15A—C15—H15B109.5
C4—N1—C5109.53 (13)C12—C15—H15C109.5
C16—N2—C17119.34 (13)H15A—C15—H15C109.5
N1—C1—C2110.06 (16)H15B—C15—H15C109.5
N1—C1—H1A109.6C12—C13'—H13D109.5
C2—C1—H1A109.6C12—C13'—H13E109.5
N1—C1—H1B109.6H13D—C13'—H13E109.5
C2—C1—H1B109.6C12—C13'—H13F109.5
H1A—C1—H1B108.2H13D—C13'—H13F109.5
O1—C2—C1110.94 (17)H13E—C13'—H13F109.5
O1—C2—H2A109.5C12—C14'—H14D109.5
C1—C2—H2A109.5C12—C14'—H14E109.5
O1—C2—H2B109.5H14D—C14'—H14E109.5
C1—C2—H2B109.5C12—C14'—H14F109.5
H2A—C2—H2B108.0H14D—C14'—H14F109.5
O1—C3—C4111.61 (15)H14E—C14'—H14F109.5
O1—C3—H3A109.3C12—C15'—H15D109.5
C4—C3—H3A109.3C12—C15'—H15E109.5
O1—C3—H3B109.3H15D—C15'—H15E109.5
C4—C3—H3B109.3C12—C15'—H15F109.5
H3A—C3—H3B108.0H15D—C15'—H15F109.5
N1—C4—C3111.01 (15)H15E—C15'—H15F109.5
N1—C4—H4A109.4N2—C16—C8121.77 (14)
C3—C4—H4A109.4N2—C16—H16A119.1
N1—C4—H4B109.4C8—C16—H16A119.1
C3—C4—H4B109.4C22—C17—C18122.30 (15)
H4A—C4—H4B108.0C22—C17—N2121.22 (15)
N1—C5—C6113.49 (14)C18—C17—N2116.34 (15)
N1—C5—H5A108.9C19—C18—C17117.09 (16)
C6—C5—H5A108.9C19—C18—C26122.42 (17)
N1—C5—H5B108.9C17—C18—C26120.48 (15)
C6—C5—H5B108.9C20—C19—C18121.78 (18)
H5A—C5—H5B107.7C20—C19—H19A119.1
C11—C6—C7118.20 (14)C18—C19—H19A119.1
C11—C6—C5122.14 (15)C19—C20—C21119.79 (17)
C7—C6—C5119.65 (14)C19—C20—H20A120.1
O2—C7—C6118.90 (14)C21—C20—H20A120.1
O2—C7—C8121.14 (14)C20—C21—C22121.81 (18)
C6—C7—C8119.95 (14)C20—C21—H21A119.1
C7—C8—C9119.60 (14)C22—C21—H21A119.1
C7—C8—C16120.56 (14)C21—C22—C17116.98 (18)
C9—C8—C16119.83 (14)C21—C22—C23119.96 (16)
C10—C9—C8121.83 (14)C17—C22—C23122.93 (16)
C10—C9—H9A119.1C25—C23—C22112.08 (18)
C8—C9—H9A119.1C25—C23—C24110.91 (17)
C9—C10—C11116.59 (14)C22—C23—C24110.57 (16)
C9—C10—C12123.67 (14)C25—C23—H23A107.7
C11—C10—C12119.74 (14)C22—C23—H23A107.7
C6—C11—C10123.83 (15)C24—C23—H23A107.7
C6—C11—H11A118.1C23—C24—H24A109.5
C10—C11—H11A118.1C23—C24—H24B109.5
C15'—C12—C14'110.3 (6)H24A—C24—H24B109.5
C15'—C12—C13113.6 (9)C23—C24—H24C109.5
C14'—C12—C1389.3 (6)H24A—C24—H24C109.5
C14'—C12—C15123.4 (6)H24B—C24—H24C109.5
C13—C12—C15108.2 (8)C23—C25—H25A109.5
C15'—C12—C10116.1 (6)C23—C25—H25B109.5
C14'—C12—C10110.0 (5)H25A—C25—H25B109.5
C13—C12—C10114.2 (6)C23—C25—H25C109.5
C15—C12—C10110.2 (5)H25A—C25—H25C109.5
C15'—C12—C13'107.2 (7)H25B—C25—H25C109.5
C14'—C12—C13'107.0 (6)C18—C26—C27111.01 (17)
C15—C12—C13'98.6 (7)C18—C26—C28113.29 (16)
C10—C12—C13'105.6 (4)C27—C26—C28110.46 (18)
C15'—C12—C1492.7 (6)C18—C26—H26A107.3
C13—C12—C14111.3 (6)C27—C26—H26A107.3
C15—C12—C14106.2 (6)C28—C26—H26A107.3
C10—C12—C14106.5 (4)C26—C27—H27A109.5
C13'—C12—C14129.0 (5)C26—C27—H27B109.5
C12—C13—H13A109.5H27A—C27—H27B109.5
C12—C13—H13B109.5C26—C27—H27C109.5
H13A—C13—H13B109.5H27A—C27—H27C109.5
C12—C13—H13C109.5H27B—C27—H27C109.5
H13A—C13—H13C109.5C26—C28—H28A109.5
H13B—C13—H13C109.5C26—C28—H28B109.5
C12—C14—H14A109.5H28A—C28—H28B109.5
C12—C14—H14B109.5C26—C28—H28C109.5
H14A—C14—H14B109.5H28A—C28—H28C109.5
C12—C14—H14C109.5H28B—C28—H28C109.5
H14A—C14—H14C109.5
C4—N1—C1—C257.0 (2)C9—C10—C12—C15−12.5 (6)
C5—N1—C1—C2177.71 (15)C11—C10—C12—C15167.6 (5)
C3—O1—C2—C160.1 (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—C14102.2 (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—N157.4 (2)C7—C8—C16—N20.8 (2)
C1—N1—C5—C666.21 (19)C9—C8—C16—N2179.50 (15)
C4—N1—C5—C6−173.56 (15)C16—N2—C17—C22−70.8 (2)
N1—C5—C6—C1134.2 (2)C16—N2—C17—C18113.33 (18)
N1—C5—C6—C7−147.46 (15)C22—C17—C18—C195.7 (3)
C11—C6—C7—O2−179.73 (14)N2—C17—C18—C19−178.39 (15)
C5—C6—C7—O21.8 (2)C22—C17—C18—C26−175.61 (16)
C11—C6—C7—C8−0.2 (2)N2—C17—C18—C260.3 (2)
C5—C6—C7—C8−178.66 (15)C17—C18—C19—C20−2.2 (3)
O2—C7—C8—C9179.79 (14)C26—C18—C19—C20179.14 (18)
C6—C7—C8—C90.3 (2)C18—C19—C20—C21−1.5 (3)
O2—C7—C8—C16−1.5 (2)C19—C20—C21—C221.9 (3)
C6—C7—C8—C16178.97 (14)C20—C21—C22—C171.4 (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—C110.7 (2)N2—C17—C22—C21179.01 (15)
C8—C9—C10—C12−179.16 (15)C18—C17—C22—C23170.59 (17)
C7—C6—C11—C100.4 (2)N2—C17—C22—C23−5.1 (3)
C5—C6—C11—C10178.80 (16)C21—C22—C23—C25−55.3 (2)
C9—C10—C11—C6−0.6 (2)C17—C22—C23—C25128.9 (2)
C12—C10—C11—C6179.22 (15)C21—C22—C23—C2469.0 (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—C2785.8 (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—C28142.27 (18)
C11—C10—C12—C1345.6 (6)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H2···N20.821.832.5630 (18)148
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H2···N20.821.832.5630 (18)148
references
References top

Blessing, R. H. (1995). Acta Cryst. A51, 33–38.

Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.

Gibson, V. C. & Spitzmesser, S. K. (2003). Chem. Rev. 103, 283–315.

Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Younkin, T. R., Conner, E. F., Henderson, J. I., Friedrich, S. K., Grubbs, R. H. & Bansleben, D. A. (2000). Science, 287, 460–462.