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Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): o410.
Published online 2008 January 9. doi:  10.1107/S1600536807068365
PMCID: PMC2960411

2,6-Di-tert-butyl-4-[(N-methyl­anilino)meth­yl]phenol

Abstract

The title compound, C22H31NO, has been synthesized from 4-bromo­methyl-2,6-di-tert-butyl­phenol and N-methyl­aniline. There are two independent mol­ecules in the asymmetric unit. The aniline ring in each of the independent mol­ecules was found to be disordered, with site occupation factors 0.621 (10)/0.379 (10) and 0.605 (10)/0.395 (10).

Related literature

For related literature, see: Yamazaki & Seguchi (1997 [triangle]); Rieker et al. (1968 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o410-scheme1.jpg

Experimental

Crystal data

  • C22H31NO
  • M r = 325.48
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o410-efi1.jpg
  • a = 9.535 (7) Å
  • b = 12.106 (9) Å
  • c = 17.959 (14) Å
  • α = 109.561 (13)°
  • β = 92.691 (13)°
  • γ = 90.394 (14)°
  • V = 1951 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 294 (2) K
  • 0.24 × 0.24 × 0.20 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.984, T max = 0.987
  • 10188 measured reflections
  • 6861 independent reflections
  • 3684 reflections with I > 2σ(I)
  • R int = 0.026

Refinement

  • R[F 2 > 2σ(F 2)] = 0.054
  • wR(F 2) = 0.165
  • S = 1.02
  • 6861 reflections
  • 510 parameters
  • 472 restraints
  • H-atom parameters constrained
  • Δρmax = 0.25 e Å−3
  • Δρmin = −0.31 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Bruker, 1997 [triangle]); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807068365/lw2054sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807068365/lw2054Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors gratefully acknowledge financial support from the Start Foundation for Doctors of Yantai University.

supplementary crystallographic information

Comment

Hindered phenol antioxidants are widely used in polymers and lubricants. They protect polymers by increasing both their process stability and long-term stability against oxidative degradation (Yamazaki and Seguchi, 1997).

There are two independent molecules in the crystal structure. Both of the two aniline rings in the two independent molecules were found disordered.

The bond lengths and angles of the crystal are within normal ranges and selected values are given in Table 1.

Experimental

The 4-bromomethyl-2,6-di-tert-butyl-phenol was synthesized according to the method described by Rieker et al. (1968). N-methylaniline (3.21 g, 0.03 mol) and 4-bromomethyl-2,6-di-tert-butyl-phenol (9.0 g, 0.03 mol) were added, with stirring to THF(40 ml) at 278 K. The reaction mixture was stirred at 278–283 K for a further 2 h. then a solution of Na2CO3(1.60 g, 0.015 mol) in water (10 ml) was added. The solvent THF was evaporated under reduced pressure and the product was extracted by diethyl ether. The product (7.95 g) was obtained in a yield of 81.4%. Suitable crystals were obtained by slow evaporation of a mixture of ethyl acetate and methanol.

Refinement

The phenyl goups of amines were disordered in tow positions with occupy fators 0.605 (10)/0.395 (10) and 0.621 (10)/0.379 (10) respectively. The disordered phenyl groups were constrained to a hexagon with the C—C distances 1.39 A. The H atoms of O—H were restrained on their parent atoms with O—H restrained 0.83 and 0.84Å at positions based on difference map peaks close to the parent O atoms.. In absence of significant anomalous dispersion effects, Friedel-pair reflections were merged prior to refinement. All H other atoms were positioned geometrically and refined using a riding model, in the range of 0.93–0.97 Å, with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The two crystallygraphically independent molecules in the structure of (I). Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii. To be clarity, the disordered part of phenyl rings (C17' ...
Fig. 2.
The packing diagram of (I).

Crystal data

C22H31NOZ = 4
Mr = 325.48F000 = 712
Triclinic, P1Dx = 1.108 Mg m3
a = 9.535 (7) ÅMo Kα radiation λ = 0.71073 Å
b = 12.106 (9) ÅCell parameters from 2492 reflections
c = 17.959 (14) Åθ = 2.4–23.5º
α = 109.561 (13)ºµ = 0.07 mm1
β = 92.691 (13)ºT = 294 (2) K
γ = 90.394 (14)ºBolck, colourless
V = 1951 (3) Å30.24 × 0.24 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer6861 independent reflections
Radiation source: fine-focus sealed tube3684 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.026
T = 294(2) Kθmax = 25.0º
[var phi] and ω scansθmin = 1.2º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −11→11
Tmin = 0.984, Tmax = 0.987k = −14→9
10188 measured reflectionsl = −21→21

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.054H-atom parameters constrained
wR(F2) = 0.165  w = 1/[σ2(Fo2) + (0.0658P)2 + 0.5357P] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.004
6861 reflectionsΔρmax = 0.25 e Å3
510 parametersΔρmin = −0.31 e Å3
472 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0156 (16)

Special details

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)

xyzUiso*/UeqOcc. (<1)
O11.02388 (18)0.41746 (16)0.41523 (10)0.0651 (5)
H10.97880.38120.43930.078*
O20.55834 (18)0.91928 (16)0.41754 (10)0.0643 (5)
H20.60270.88310.44280.077*
N10.8263 (3)0.0870 (2)0.06541 (13)0.0699 (7)
N20.6869 (3)0.5888 (2)0.06764 (13)0.0707 (7)
C11.0031 (2)0.3369 (2)0.34025 (14)0.0432 (6)
C21.1039 (2)0.2513 (2)0.31399 (14)0.0414 (6)
C31.0841 (2)0.1748 (2)0.23807 (15)0.0469 (6)
H31.14940.11660.21910.056*
C40.9719 (3)0.1805 (2)0.18891 (14)0.0485 (6)
C50.8740 (2)0.2641 (2)0.21751 (14)0.0464 (6)
H50.79740.26770.18440.056*
C60.8845 (2)0.3435 (2)0.29364 (14)0.0417 (6)
C70.7697 (3)0.4322 (2)0.32466 (15)0.0514 (7)
C80.8241 (3)0.5576 (3)0.3400 (2)0.0804 (10)
H8A0.85740.56410.29200.121*
H8B0.89960.57600.37980.121*
H8C0.74940.61130.35790.121*
C90.6445 (3)0.4117 (3)0.26502 (17)0.0695 (8)
H9A0.57330.46720.28690.104*
H9B0.60720.33360.25340.104*
H9C0.67440.42150.21730.104*
C100.7112 (3)0.4194 (3)0.39917 (17)0.0714 (9)
H10A0.63620.47310.41630.107*
H10B0.78440.43640.44030.107*
H10C0.67630.34060.38780.107*
C111.2294 (2)0.2416 (2)0.36724 (15)0.0525 (7)
C121.3197 (3)0.3536 (3)0.39181 (18)0.0712 (9)
H12A1.39910.34600.42450.107*
H12B1.26510.41880.42090.107*
H12C1.35190.36660.34550.107*
C131.3231 (3)0.1410 (3)0.32503 (19)0.0792 (9)
H13A1.36050.15490.28020.119*
H13B1.26900.06890.30750.119*
H13C1.39880.13580.36080.119*
C141.1797 (3)0.2174 (3)0.43998 (17)0.0742 (9)
H14A1.12900.14380.42370.111*
H14B1.11940.27890.46820.111*
H14C1.25950.21450.47380.111*
C150.9607 (3)0.0940 (3)0.10617 (16)0.0725 (9)
H15A1.03110.11480.07560.087*
H15B0.98240.01700.10830.087*
C160.7267 (4)0.0108 (4)0.0818 (2)0.1105 (13)
H16A0.63400.04060.07980.166*
H16B0.74820.00670.13360.166*
H16C0.7308−0.06610.04320.166*
C170.8148 (8)0.1256 (7)0.0005 (3)0.0610 (17)0.605 (10)
C180.9201 (7)0.1988 (6)−0.0091 (3)0.0751 (17)0.605 (10)
H18A0.99570.22210.02780.090*0.605 (10)
C190.9126 (7)0.2373 (5)−0.0739 (3)0.0833 (18)0.605 (10)
H19A0.98310.2863−0.08040.100*0.605 (10)
C200.7997 (8)0.2025 (6)−0.1291 (3)0.084 (2)0.605 (10)
H20A0.79470.2282−0.17250.101*0.605 (10)
C210.6944 (6)0.1292 (7)−0.1195 (3)0.083 (2)0.605 (10)
H21A0.61890.1059−0.15640.100*0.605 (10)
C220.7019 (7)0.0908 (6)−0.0547 (4)0.0725 (16)0.605 (10)
H22A0.63140.0418−0.04820.087*0.605 (10)
C17'0.8006 (13)0.1132 (11)−0.0028 (5)0.061 (2)0.395 (10)
C18'0.8780 (11)0.1974 (10)−0.0213 (5)0.071 (2)0.395 (10)
H18B0.95140.23840.01290.086*0.395 (10)
C19'0.8455 (12)0.2203 (8)−0.0909 (5)0.085 (2)0.395 (10)
H19B0.89720.2766−0.10330.102*0.395 (10)
C20'0.7357 (12)0.1589 (9)−0.1420 (4)0.079 (3)0.395 (10)
H20B0.71400.1742−0.18860.095*0.395 (10)
C21'0.6584 (9)0.0748 (10)−0.1235 (5)0.084 (2)0.395 (10)
H21B0.58490.0337−0.15770.100*0.395 (10)
C22'0.6909 (11)0.0519 (10)−0.0539 (5)0.073 (2)0.395 (10)
H22B0.6391−0.0044−0.04150.087*0.395 (10)
C230.5635 (2)0.8380 (2)0.34270 (14)0.0435 (6)
C240.4570 (2)0.7526 (2)0.31693 (14)0.0417 (6)
C250.4620 (2)0.6758 (2)0.24087 (14)0.0459 (6)
H250.39230.61770.22190.055*
C260.5657 (3)0.6814 (2)0.19177 (14)0.0483 (6)
C270.6696 (3)0.7653 (2)0.22026 (15)0.0489 (6)
H270.74060.76880.18730.059*
C280.6733 (2)0.8452 (2)0.29632 (14)0.0430 (6)
C290.7944 (3)0.9346 (2)0.32725 (15)0.0512 (7)
C300.7421 (3)1.0594 (3)0.3435 (2)0.0813 (10)
H30A0.82021.11400.36020.122*
H30B0.67611.07690.38440.122*
H30C0.69721.06550.29610.122*
C310.8662 (3)0.9218 (3)0.40190 (16)0.0665 (8)
H31A0.89650.84270.39070.100*
H31B0.80110.94010.44330.100*
H31C0.94600.97470.41850.100*
C320.9081 (3)0.9143 (3)0.26745 (18)0.0716 (9)
H32A0.86910.92260.21940.107*
H32B0.94350.83680.25650.107*
H32C0.98330.97090.28880.107*
C330.3407 (2)0.7418 (2)0.36998 (15)0.0516 (7)
C340.4034 (3)0.7176 (3)0.44301 (17)0.0764 (9)
H34A0.32910.70930.47520.115*
H34B0.46490.78180.47310.115*
H34C0.45540.64670.42650.115*
C350.2552 (3)0.8536 (3)0.39465 (19)0.0754 (9)
H35A0.21430.86610.34830.113*
H35B0.31570.91920.42350.113*
H35C0.18210.84570.42760.113*
C360.2386 (3)0.6414 (3)0.32762 (19)0.0809 (10)
H36A0.19430.65510.28250.121*
H36B0.16840.63630.36300.121*
H36C0.28840.56930.31050.121*
C370.5604 (3)0.5946 (3)0.10895 (16)0.0724 (9)
H37A0.53910.51740.11130.087*
H37B0.48390.61470.07860.087*
C380.7901 (4)0.5130 (4)0.0833 (2)0.1084 (13)
H38A0.77660.43560.04530.163*
H38B0.78070.51010.13560.163*
H38C0.88230.54250.07950.163*
C390.6836 (7)0.6260 (6)0.0019 (3)0.0625 (17)0.621 (10)
C400.5768 (7)0.6981 (6)−0.0081 (3)0.0727 (16)0.621 (10)
H40A0.50860.72170.02900.087*0.621 (10)
C410.5720 (7)0.7351 (5)−0.0736 (3)0.0802 (17)0.621 (10)
H41A0.50050.7834−0.08030.096*0.621 (10)
C420.6739 (7)0.6999 (6)−0.1291 (3)0.0838 (19)0.621 (10)
H42A0.67070.7246−0.17290.101*0.621 (10)
C430.7807 (6)0.6278 (7)−0.1191 (3)0.0820 (19)0.621 (10)
H43A0.84900.6042−0.15620.098*0.621 (10)
C440.7856 (6)0.5908 (6)−0.0536 (3)0.0715 (15)0.621 (10)
H44A0.85700.5425−0.04700.086*0.621 (10)
C39'0.7001 (13)0.6128 (11)−0.0017 (5)0.063 (2)0.379 (10)
C40'0.6191 (12)0.6958 (10)−0.0204 (5)0.073 (2)0.379 (10)
H40B0.55300.73710.01420.088*0.379 (10)
C41'0.6366 (12)0.7171 (8)−0.0909 (5)0.083 (3)0.379 (10)
H41B0.58240.7726−0.10340.100*0.379 (10)
C42'0.7353 (12)0.6554 (9)−0.1426 (4)0.077 (3)0.379 (10)
H42B0.74700.6696−0.18970.093*0.379 (10)
C43'0.8164 (9)0.5724 (10)−0.1239 (5)0.085 (2)0.379 (10)
H43B0.88240.5311−0.15840.101*0.379 (10)
C44'0.7988 (11)0.5512 (10)−0.0534 (6)0.076 (2)0.379 (10)
H44B0.85300.4956−0.04090.091*0.379 (10)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0643 (12)0.0726 (13)0.0444 (11)−0.0033 (10)−0.0048 (9)0.0022 (10)
O20.0628 (12)0.0703 (13)0.0475 (11)0.0003 (9)0.0070 (9)0.0029 (10)
N10.0725 (17)0.0811 (18)0.0475 (15)−0.0112 (13)−0.0130 (12)0.0124 (13)
N20.0778 (17)0.0805 (18)0.0485 (15)0.0116 (14)0.0158 (12)0.0127 (13)
C10.0411 (14)0.0476 (15)0.0379 (14)−0.0039 (11)−0.0004 (11)0.0109 (12)
C20.0350 (13)0.0479 (15)0.0429 (15)−0.0026 (11)−0.0004 (11)0.0177 (12)
C30.0432 (14)0.0455 (15)0.0516 (16)0.0038 (11)0.0043 (12)0.0155 (13)
C40.0471 (15)0.0515 (16)0.0428 (15)0.0014 (12)0.0004 (12)0.0106 (12)
C50.0421 (14)0.0568 (16)0.0414 (15)0.0018 (12)−0.0043 (11)0.0187 (13)
C60.0383 (13)0.0447 (14)0.0428 (15)0.0004 (10)0.0010 (11)0.0160 (12)
C70.0469 (15)0.0499 (16)0.0571 (17)0.0059 (12)0.0027 (12)0.0175 (13)
C80.082 (2)0.055 (2)0.102 (3)0.0074 (16)0.0060 (19)0.0233 (18)
C90.0525 (17)0.082 (2)0.075 (2)0.0202 (15)−0.0028 (15)0.0274 (17)
C100.0568 (17)0.090 (2)0.067 (2)0.0140 (16)0.0169 (15)0.0239 (17)
C110.0417 (14)0.0630 (18)0.0549 (17)−0.0010 (13)−0.0057 (12)0.0238 (14)
C120.0488 (16)0.086 (2)0.080 (2)−0.0135 (15)−0.0104 (15)0.0326 (18)
C130.0593 (18)0.092 (2)0.085 (2)0.0227 (17)−0.0095 (16)0.0297 (19)
C140.0699 (19)0.097 (2)0.068 (2)−0.0063 (17)−0.0130 (16)0.0463 (19)
C150.074 (2)0.079 (2)0.0503 (18)0.0122 (16)−0.0069 (15)0.0034 (16)
C160.118 (3)0.121 (3)0.095 (3)−0.034 (3)−0.012 (2)0.042 (2)
C170.065 (3)0.058 (3)0.044 (3)0.014 (3)−0.002 (2)−0.004 (3)
C180.082 (4)0.065 (3)0.069 (3)0.013 (3)0.001 (3)0.010 (3)
C190.087 (4)0.080 (3)0.082 (3)0.015 (3)0.004 (3)0.026 (3)
C200.095 (4)0.087 (4)0.068 (3)0.014 (3)−0.005 (3)0.024 (3)
C210.089 (4)0.088 (4)0.069 (3)0.018 (3)−0.004 (3)0.023 (3)
C220.073 (3)0.079 (4)0.057 (3)0.012 (3)−0.003 (2)0.012 (3)
C17'0.071 (4)0.055 (4)0.050 (4)0.013 (3)0.005 (3)0.007 (3)
C18'0.080 (4)0.063 (4)0.066 (4)0.013 (4)0.002 (3)0.015 (3)
C19'0.091 (5)0.077 (4)0.082 (4)0.011 (4)0.001 (4)0.022 (4)
C20'0.091 (5)0.076 (4)0.075 (4)0.016 (4)0.001 (4)0.033 (4)
C21'0.094 (4)0.086 (5)0.066 (4)0.023 (4)−0.001 (3)0.018 (4)
C22'0.078 (4)0.077 (5)0.052 (3)0.023 (4)−0.007 (3)0.008 (3)
C230.0429 (14)0.0455 (15)0.0373 (14)0.0023 (11)0.0005 (11)0.0078 (12)
C240.0373 (13)0.0456 (14)0.0444 (15)0.0035 (11)0.0013 (11)0.0181 (12)
C250.0416 (14)0.0464 (15)0.0471 (16)−0.0054 (11)−0.0049 (11)0.0135 (13)
C260.0478 (15)0.0522 (16)0.0403 (15)−0.0016 (12)0.0005 (12)0.0100 (12)
C270.0469 (15)0.0572 (17)0.0449 (16)−0.0014 (12)0.0102 (12)0.0190 (13)
C280.0409 (14)0.0441 (14)0.0459 (15)0.0013 (11)0.0005 (11)0.0179 (12)
C290.0488 (15)0.0475 (16)0.0569 (17)−0.0064 (12)0.0000 (12)0.0177 (13)
C300.078 (2)0.0521 (19)0.111 (3)−0.0090 (16)−0.0032 (19)0.0261 (18)
C310.0524 (16)0.080 (2)0.0643 (19)−0.0107 (14)−0.0093 (14)0.0219 (16)
C320.0572 (17)0.083 (2)0.077 (2)−0.0221 (15)0.0062 (15)0.0302 (18)
C330.0410 (14)0.0634 (18)0.0519 (16)0.0011 (13)0.0057 (12)0.0208 (14)
C340.075 (2)0.107 (3)0.063 (2)0.0053 (18)0.0124 (16)0.0478 (19)
C350.0522 (17)0.089 (2)0.084 (2)0.0163 (16)0.0162 (15)0.0257 (19)
C360.0620 (19)0.095 (2)0.085 (2)−0.0220 (17)0.0149 (16)0.0278 (19)
C370.075 (2)0.080 (2)0.0504 (18)−0.0099 (16)0.0108 (15)0.0059 (16)
C380.119 (3)0.119 (3)0.096 (3)0.041 (3)0.019 (2)0.046 (2)
C390.068 (3)0.060 (3)0.044 (3)−0.012 (3)0.004 (2)−0.002 (2)
C400.081 (4)0.064 (3)0.065 (3)−0.010 (3)0.006 (3)0.010 (2)
C410.088 (4)0.072 (3)0.080 (3)−0.011 (3)−0.002 (3)0.025 (3)
C420.097 (4)0.086 (4)0.066 (3)−0.016 (3)0.013 (3)0.022 (3)
C430.088 (4)0.086 (4)0.069 (3)−0.018 (3)0.008 (3)0.023 (3)
C440.075 (3)0.079 (4)0.054 (3)−0.010 (3)0.010 (2)0.013 (3)
C39'0.074 (4)0.057 (4)0.052 (4)−0.011 (3)−0.001 (3)0.010 (3)
C40'0.083 (4)0.063 (4)0.067 (4)−0.013 (4)0.002 (3)0.015 (3)
C41'0.091 (5)0.077 (4)0.080 (4)−0.008 (4)0.004 (4)0.025 (4)
C42'0.088 (5)0.079 (4)0.072 (4)−0.013 (4)0.004 (4)0.034 (4)
C43'0.095 (4)0.087 (5)0.067 (4)−0.022 (4)0.008 (4)0.019 (4)
C44'0.083 (4)0.081 (5)0.055 (4)−0.021 (4)0.008 (3)0.009 (4)

Geometric parameters (Å, °)

O1—C11.377 (3)C19'—H19B0.9300
O1—H10.8404C20'—C21'1.3900
O2—C231.378 (3)C20'—H20B0.9300
O2—H20.8327C21'—C22'1.3900
N1—C17'1.376 (6)C21'—H21B0.9300
N1—C171.393 (4)C22'—H22B0.9300
N1—C161.427 (4)C23—C281.388 (3)
N1—C151.433 (4)C23—C241.391 (3)
N2—C39'1.381 (6)C24—C251.374 (3)
N2—C391.397 (4)C24—C331.528 (3)
N2—C381.431 (4)C25—C261.372 (3)
N2—C371.436 (4)C25—H250.9300
C1—C61.394 (3)C26—C271.366 (3)
C1—C21.397 (3)C26—C371.505 (4)
C2—C31.371 (3)C27—C281.383 (3)
C2—C111.526 (3)C27—H270.9300
C3—C41.372 (3)C28—C291.528 (3)
C3—H30.9300C29—C321.525 (4)
C4—C51.367 (3)C29—C311.531 (4)
C4—C151.503 (4)C29—C301.531 (4)
C5—C61.381 (3)C30—H30A0.9600
C5—H50.9300C30—H30B0.9600
C6—C71.528 (3)C30—H30C0.9600
C7—C91.527 (4)C31—H31A0.9600
C7—C101.528 (4)C31—H31B0.9600
C7—C81.531 (4)C31—H31C0.9600
C8—H8A0.9600C32—H32A0.9600
C8—H8B0.9600C32—H32B0.9600
C8—H8C0.9600C32—H32C0.9600
C9—H9A0.9600C33—C361.516 (4)
C9—H9B0.9600C33—C351.530 (4)
C9—H9C0.9600C33—C341.532 (4)
C10—H10A0.9600C34—H34A0.9600
C10—H10B0.9600C34—H34B0.9600
C10—H10C0.9600C34—H34C0.9600
C11—C131.522 (4)C35—H35A0.9600
C11—C121.524 (4)C35—H35B0.9600
C11—C141.526 (4)C35—H35C0.9600
C12—H12A0.9600C36—H36A0.9600
C12—H12B0.9600C36—H36B0.9600
C12—H12C0.9600C36—H36C0.9600
C13—H13A0.9600C37—H37A0.9700
C13—H13B0.9600C37—H37B0.9700
C13—H13C0.9600C38—H38A0.9600
C14—H14A0.9600C38—H38B0.9600
C14—H14B0.9600C38—H38C0.9600
C14—H14C0.9600C39—C401.3900
C15—H15A0.9700C39—C441.3900
C15—H15B0.9700C40—C411.3900
C16—H16A0.9600C40—H40A0.9300
C16—H16B0.9600C41—C421.3900
C16—H16C0.9600C41—H41A0.9300
C17—C181.3900C42—C431.3900
C17—C221.3900C42—H42A0.9300
C18—C191.3900C43—C441.3900
C18—H18A0.9300C43—H43A0.9300
C19—C201.3900C44—H44A0.9300
C19—H19A0.9300C39'—C40'1.3900
C20—C211.3900C39'—C44'1.3900
C20—H20A0.9300C40'—C41'1.3900
C21—C221.3900C40'—H40B0.9300
C21—H21A0.9300C41'—C42'1.3900
C22—H22A0.9300C41'—H41B0.9300
C17'—C18'1.3900C42'—C43'1.3900
C17'—C22'1.3900C42'—H42B0.9300
C18'—C19'1.3900C43'—C44'1.3900
C18'—H18B0.9300C43'—H43B0.9300
C19'—C20'1.3900C44'—H44B0.9300
C1—O1—H197.6C19'—C20'—H20B120.0
C23—O2—H298.8C22'—C21'—C20'120.0
C17'—N1—C177.9 (7)C22'—C21'—H21B120.0
C17'—N1—C16116.7 (5)C20'—C21'—H21B120.0
C17—N1—C16124.4 (4)C21'—C22'—C17'120.0
C17'—N1—C15125.5 (5)C21'—C22'—H22B120.0
C17—N1—C15118.9 (4)C17'—C22'—H22B120.0
C16—N1—C15114.2 (3)O2—C23—C28118.9 (2)
C39'—N2—C399.1 (7)O2—C23—C24118.1 (2)
C39'—N2—C38115.4 (5)C28—C23—C24123.0 (2)
C39—N2—C38124.4 (3)C25—C24—C23116.6 (2)
C39'—N2—C37126.2 (6)C25—C24—C33120.8 (2)
C39—N2—C37118.3 (4)C23—C24—C33122.5 (2)
C38—N2—C37114.4 (3)C26—C25—C24122.7 (2)
O1—C1—C6119.7 (2)C26—C25—H25118.7
O1—C1—C2117.7 (2)C24—C25—H25118.7
C6—C1—C2122.6 (2)C27—C26—C25118.6 (2)
C3—C2—C1116.8 (2)C27—C26—C37122.8 (2)
C3—C2—C11121.3 (2)C25—C26—C37118.6 (2)
C1—C2—C11121.9 (2)C26—C27—C28122.5 (2)
C2—C3—C4122.7 (2)C26—C27—H27118.8
C2—C3—H3118.6C28—C27—H27118.8
C4—C3—H3118.6C27—C28—C23116.6 (2)
C5—C4—C3118.6 (2)C27—C28—C29121.0 (2)
C5—C4—C15122.6 (2)C23—C28—C29122.4 (2)
C3—C4—C15118.8 (2)C32—C29—C28111.4 (2)
C4—C5—C6122.5 (2)C32—C29—C31105.8 (2)
C4—C5—H5118.7C28—C29—C31110.4 (2)
C6—C5—H5118.7C32—C29—C30107.7 (2)
C5—C6—C1116.7 (2)C28—C29—C30110.6 (2)
C5—C6—C7121.0 (2)C31—C29—C30110.8 (2)
C1—C6—C7122.3 (2)C29—C30—H30A109.5
C9—C7—C10105.6 (2)C29—C30—H30B109.5
C9—C7—C6111.6 (2)H30A—C30—H30B109.5
C10—C7—C6110.6 (2)C29—C30—H30C109.5
C9—C7—C8106.6 (2)H30A—C30—H30C109.5
C10—C7—C8111.1 (2)H30B—C30—H30C109.5
C6—C7—C8111.1 (2)C29—C31—H31A109.5
C7—C8—H8A109.5C29—C31—H31B109.5
C7—C8—H8B109.5H31A—C31—H31B109.5
H8A—C8—H8B109.5C29—C31—H31C109.5
C7—C8—H8C109.5H31A—C31—H31C109.5
H8A—C8—H8C109.5H31B—C31—H31C109.5
H8B—C8—H8C109.5C29—C32—H32A109.5
C7—C9—H9A109.5C29—C32—H32B109.5
C7—C9—H9B109.5H32A—C32—H32B109.5
H9A—C9—H9B109.5C29—C32—H32C109.5
C7—C9—H9C109.5H32A—C32—H32C109.5
H9A—C9—H9C109.5H32B—C32—H32C109.5
H9B—C9—H9C109.5C36—C33—C24111.9 (2)
C7—C10—H10A109.5C36—C33—C35106.8 (2)
C7—C10—H10B109.5C24—C33—C35110.1 (2)
H10A—C10—H10B109.5C36—C33—C34107.0 (2)
C7—C10—H10C109.5C24—C33—C34110.4 (2)
H10A—C10—H10C109.5C35—C33—C34110.5 (2)
H10B—C10—H10C109.5C33—C34—H34A109.5
C13—C11—C12107.1 (2)C33—C34—H34B109.5
C13—C11—C2111.7 (2)H34A—C34—H34B109.5
C12—C11—C2110.2 (2)C33—C34—H34C109.5
C13—C11—C14106.8 (2)H34A—C34—H34C109.5
C12—C11—C14110.5 (2)H34B—C34—H34C109.5
C2—C11—C14110.4 (2)C33—C35—H35A109.5
C11—C12—H12A109.5C33—C35—H35B109.5
C11—C12—H12B109.5H35A—C35—H35B109.5
H12A—C12—H12B109.5C33—C35—H35C109.5
C11—C12—H12C109.5H35A—C35—H35C109.5
H12A—C12—H12C109.5H35B—C35—H35C109.5
H12B—C12—H12C109.5C33—C36—H36A109.5
C11—C13—H13A109.5C33—C36—H36B109.5
C11—C13—H13B109.5H36A—C36—H36B109.5
H13A—C13—H13B109.5C33—C36—H36C109.5
C11—C13—H13C109.5H36A—C36—H36C109.5
H13A—C13—H13C109.5H36B—C36—H36C109.5
H13B—C13—H13C109.5N2—C37—C26114.9 (2)
C11—C14—H14A109.5N2—C37—H37A108.5
C11—C14—H14B109.5C26—C37—H37A108.5
H14A—C14—H14B109.5N2—C37—H37B108.5
C11—C14—H14C109.5C26—C37—H37B108.5
H14A—C14—H14C109.5H37A—C37—H37B107.5
H14B—C14—H14C109.5N2—C38—H38A109.5
N1—C15—C4115.1 (2)N2—C38—H38B109.5
N1—C15—H15A108.5H38A—C38—H38B109.5
C4—C15—H15A108.5N2—C38—H38C109.5
N1—C15—H15B108.5H38A—C38—H38C109.5
C4—C15—H15B108.5H38B—C38—H38C109.5
H15A—C15—H15B107.5C40—C39—C44120.0
N1—C16—H16A109.5C40—C39—N2119.5 (4)
N1—C16—H16B109.5C44—C39—N2120.5 (4)
H16A—C16—H16B109.5C41—C40—C39120.0
N1—C16—H16C109.5C41—C40—H40A120.0
H16A—C16—H16C109.5C39—C40—H40A120.0
H16B—C16—H16C109.5C42—C41—C40120.0
C18—C17—C22120.0C42—C41—H41A120.0
C18—C17—N1118.7 (4)C40—C41—H41A120.0
C22—C17—N1121.3 (4)C41—C42—C43120.0
C17—C18—C19120.0C41—C42—H42A120.0
C17—C18—H18A120.0C43—C42—H42A120.0
C19—C18—H18A120.0C44—C43—C42120.0
C20—C19—C18120.0C44—C43—H43A120.0
C20—C19—H19A120.0C42—C43—H43A120.0
C18—C19—H19A120.0C43—C44—C39120.0
C21—C20—C19120.0C43—C44—H44A120.0
C21—C20—H20A120.0C39—C44—H44A120.0
C19—C20—H20A120.0N2—C39'—C40'122.2 (7)
C20—C21—C22120.0N2—C39'—C44'117.8 (7)
C20—C21—H21A120.0C40'—C39'—C44'120.0
C22—C21—H21A120.0C41'—C40'—C39'120.0
C21—C22—C17120.0C41'—C40'—H40B120.0
C21—C22—H22A120.0C39'—C40'—H40B120.0
C17—C22—H22A120.0C42'—C41'—C40'120.0
N1—C17'—C18'123.0 (7)C42'—C41'—H41B120.0
N1—C17'—C22'117.0 (7)C40'—C41'—H41B120.0
C18'—C17'—C22'120.0C41'—C42'—C43'120.0
C19'—C18'—C17'120.0C41'—C42'—H42B120.0
C19'—C18'—H18B120.0C43'—C42'—H42B120.0
C17'—C18'—H18B120.0C44'—C43'—C42'120.0
C18'—C19'—C20'120.0C44'—C43'—H43B120.0
C18'—C19'—H19B120.0C42'—C43'—H43B120.0
C20'—C19'—H19B120.0C43'—C44'—C39'120.0
C21'—C20'—C19'120.0C43'—C44'—H44B120.0
C21'—C20'—H20B120.0C39'—C44'—H44B120.0
O1—C1—C2—C3−177.5 (2)O2—C23—C24—C25177.4 (2)
C6—C1—C2—C32.3 (3)C28—C23—C24—C25−2.1 (3)
O1—C1—C2—C113.3 (3)O2—C23—C24—C33−3.6 (3)
C6—C1—C2—C11−176.9 (2)C28—C23—C24—C33176.8 (2)
C1—C2—C3—C40.3 (3)C23—C24—C25—C260.0 (4)
C11—C2—C3—C4179.5 (2)C33—C24—C25—C26−179.0 (2)
C2—C3—C4—C5−1.7 (4)C24—C25—C26—C271.3 (4)
C2—C3—C4—C15178.9 (2)C24—C25—C26—C37−178.9 (2)
C3—C4—C5—C60.6 (4)C25—C26—C27—C28−0.6 (4)
C15—C4—C5—C6179.9 (2)C37—C26—C27—C28179.6 (3)
C4—C5—C6—C11.8 (4)C26—C27—C28—C23−1.3 (4)
C4—C5—C6—C7−177.3 (2)C26—C27—C28—C29177.5 (2)
O1—C1—C6—C5176.5 (2)O2—C23—C28—C27−176.8 (2)
C2—C1—C6—C5−3.3 (3)C24—C23—C28—C272.8 (4)
O1—C1—C6—C7−4.4 (3)O2—C23—C28—C294.4 (3)
C2—C1—C6—C7175.8 (2)C24—C23—C28—C29−176.0 (2)
C5—C6—C7—C95.4 (3)C27—C28—C29—C32−5.1 (3)
C1—C6—C7—C9−173.6 (2)C23—C28—C29—C32173.6 (2)
C5—C6—C7—C10122.7 (3)C27—C28—C29—C31−122.4 (3)
C1—C6—C7—C10−56.3 (3)C23—C28—C29—C3156.4 (3)
C5—C6—C7—C8−113.4 (3)C27—C28—C29—C30114.6 (3)
C1—C6—C7—C867.5 (3)C23—C28—C29—C30−66.6 (3)
C3—C2—C11—C130.5 (3)C25—C24—C33—C36−0.9 (3)
C1—C2—C11—C13179.6 (2)C23—C24—C33—C36−179.8 (2)
C3—C2—C11—C12119.4 (3)C25—C24—C33—C35−119.5 (3)
C1—C2—C11—C12−61.4 (3)C23—C24—C33—C3561.6 (3)
C3—C2—C11—C14−118.2 (3)C25—C24—C33—C34118.2 (3)
C1—C2—C11—C1460.9 (3)C23—C24—C33—C34−60.7 (3)
C17'—N1—C15—C4117.7 (7)C39'—N2—C37—C26−119.0 (7)
C17—N1—C15—C4112.5 (5)C39—N2—C37—C26−113.5 (5)
C16—N1—C15—C4−84.5 (4)C38—N2—C37—C2684.8 (4)
C5—C4—C15—N1−13.7 (4)C27—C26—C37—N213.1 (4)
C3—C4—C15—N1165.6 (2)C25—C26—C37—N2−166.7 (2)
C17'—N1—C17—C18−166 (7)C39'—N2—C39—C40170 (6)
C16—N1—C17—C18−179.3 (3)C38—N2—C39—C40178.9 (3)
C15—N1—C17—C18−18.1 (6)C37—N2—C39—C4019.1 (6)
C17'—N1—C17—C2213 (6)C39'—N2—C39—C44−10 (5)
C16—N1—C17—C22−0.3 (7)C38—N2—C39—C44−0.8 (7)
C15—N1—C17—C22160.9 (3)C37—N2—C39—C44−160.5 (3)
C22—C17—C18—C190.0C44—C39—C40—C410.0
N1—C17—C18—C19179.0 (7)N2—C39—C40—C41−179.6 (6)
C17—C18—C19—C200.0C39—C40—C41—C420.0
C18—C19—C20—C210.0C40—C41—C42—C430.0
C19—C20—C21—C220.0C41—C42—C43—C440.0
C20—C21—C22—C170.0C42—C43—C44—C390.0
C18—C17—C22—C210.0C40—C39—C44—C430.0
N1—C17—C22—C21−179.0 (7)N2—C39—C44—C43179.6 (6)
C17—N1—C17'—C18'4(6)C39—N2—C39'—C40'0(5)
C16—N1—C17'—C18'171.5 (5)C38—N2—C39'—C40'−172.0 (5)
C15—N1—C17'—C18'−31.1 (10)C37—N2—C39'—C40'32.0 (10)
C17—N1—C17'—C22'−176 (7)C39—N2—C39'—C44'180 (6)
C16—N1—C17'—C22'−7.9 (9)C38—N2—C39'—C44'7.8 (9)
C15—N1—C17'—C22'149.5 (4)C37—N2—C39'—C44'−148.2 (5)
N1—C17'—C18'—C19'−179.4 (11)N2—C39'—C40'—C41'179.8 (11)
C22'—C17'—C18'—C19'0.0C44'—C39'—C40'—C41'0.0
C17'—C18'—C19'—C20'0.0C39'—C40'—C41'—C42'0.0
C18'—C19'—C20'—C21'0.0C40'—C41'—C42'—C43'0.0
C19'—C20'—C21'—C22'0.0C41'—C42'—C43'—C44'0.0
C20'—C21'—C22'—C17'0.0C42'—C43'—C44'—C39'0.0
N1—C17'—C22'—C21'179.4 (10)N2—C39'—C44'—C43'−179.8 (10)
C18'—C17'—C22'—C21'0.0C40'—C39'—C44'—C43'0.0

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LW2054).

References

  • Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Rieker, A., Kaufmann, H., Bruck, D., Workmann, R. & Muller, E. (1968). Tetrahedron, 24, 103–115.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Yamazaki, T. & Seguchi, T. (1997). J. Polym. Sci. A: Polym. Chem.35, 2431–2439.

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