PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 July 1; 64(Pt 7): o1198.
Published online 2008 June 7. doi:  10.1107/S1600536808016061
PMCID: PMC2961794

2,2′-Bis(4-nitro­phen­oxy)-1,1′-binaphth­yl

Abstract

The title compound, C32H20N2O6, was synthesized by the reaction of 1,1′-binaphthyl-2,2′-diol and 4-nitro­phenol in the presence of K2CO3. The two naphthalene systems make a dihedral angle of 73.70 (5)°. The crystal packing involves mol­ecules connected by C—H(...)O hydrogen bonds into a chain along the c axis.

Related literature

For the chemistry of 1,1′-binaphthyl-2,2′-diol, see: Hiroshi et al. (2005 [triangle]); Minatti & Dötz (2005 [triangle]); Pu (1998 [triangle]); Periasamy et al. (1998 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1198-scheme1.jpg

Experimental

Crystal data

  • C32H20N2O6
  • M r = 528.50
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1198-efi1.jpg
  • a = 7.6159 (9) Å
  • b = 24.810 (3) Å
  • c = 13.5022 (15) Å
  • β = 95.790 (3)°
  • V = 2538.3 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 296 (2) K
  • 0.03 × 0.03 × 0.02 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2000 [triangle]) T min = 0.988, T max = 0.990
  • 13574 measured reflections
  • 4971 independent reflections
  • 2521 reflections with I > 2σ(I)
  • R int = 0.060

Refinement

  • R[F 2 > 2σ(F 2)] = 0.054
  • wR(F 2) = 0.114
  • S = 0.85
  • 4971 reflections
  • 361 parameters
  • H-atom parameters constrained
  • Δρmax = 0.13 e Å−3
  • Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [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 (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808016061/kp2173sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808016061/kp2173Isup2.hkl

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

Acknowledgments

This work was supported by a Start-up Grant from Southeast University to ZRQ.

supplementary crystallographic information

Comment

Axially chiral 2,2'-substituted-1,1'-binaphthyls have been extensively applied in many asymmetric processes, due to their highly stable chiral configuration with C2 symmetry (Pu, 1998). Chemists have synthesized a great number of 2,2'-substituted-1,1'-binaphthyls which have been used in asymmetric catalysis and chiral recognition (Periasamy et al., 1998). Herein we report the structure of title compound, 2,2'-substituted-1,1'-binaphthyls (Fig. 1).

In the structure of the title compoud geometric parameters are in the usual ranges. The two naphthalene rings make a dihedral angle of 73.70 (5)°. The dihedral angles between the two 4-nitrobenzene rings and the two naphthalene rings directly attached to them (ring C11–C16 between ring C1–C10 76.42 (7)° and ring C27–C32 between ring C17–C26 81.99 (7)°, respectivley) are in synclinal range. The dihedral angles between the two 4-nitrobenzene rings and the two naphthalene rings, not directly attached to them, are remarkably different: between C27–C32 and C1–C10 is 22.62 (5)° and between C11–C16 and C17–C26 is 81.87 (6)°. The two aromatic rings with the smallest dihedral angle of 22.62 (5)°) exhibit weak intramolecular π–π interaction with the separation distance 3.694 (16) an 3.8227 (17) Å between the ring centroids of the 4-nitrobenzene rings and the two six-membered rings of the naphthalene ring. In the crystal structure no classical hydrogen bond is found. The crystal packing involves C—H···O hydrogen bonds generating chain along the c axis (Table 1, Fig. 2) and a weak C—H···π interaction [C20—H20···Cg (the ring C11, C12, C13, C14, C15, C16 with symmetry opeartion x, -y + 1,-z + 1) of 3.814 (3) Å].

Experimental

1,1'-binaphthyl-2,2'-diol (1 mmol, 0.29 g) and 4-nitrophenol (2 mmol, 0.28 g) were dissolved in acetone (25 ml) in the presence of K2CO3 (1 mmol, 0.14 g) and refluxed for 2–3 days. After the mixture was cooled to room temperature, the solution was filtered and rotated in vacuum affording yellow precipitate of compound I. The crude product was recrystallized by slowly evaporating ethanol to yield colourless crystals.

Refinement

All the H atoms were positioned geometrically and were allowed to ride on the C atoms to which they are bonded, with C—H = 0.93 Å, and with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
A view of the title compound with the atomic numbering scheme. Displacement ellipsoids were drawn at the 30% probability level. H atoms have been omitted for clarity.

Crystal data

C32H20N2O6F(000) = 1096
Mr = 528.50Dx = 1.383 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1979 reflections
a = 7.6159 (9) Åθ = 3.1–27.3°
b = 24.810 (3) ŵ = 0.10 mm1
c = 13.5022 (15) ÅT = 296 K
β = 95.790 (3)°Block, colourless
V = 2538.3 (5) Å30.03 × 0.03 × 0.02 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer4971 independent reflections
Radiation source: fine-focus sealed tube2521 reflections with I > 2σ(I)
graphiteRint = 0.060
[var phi] and ω scansθmax = 26.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2000)h = −9→9
Tmin = 0.988, Tmax = 0.990k = −23→30
13574 measured reflectionsl = −16→14

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114H-atom parameters constrained
S = 0.86w = 1/[σ2(Fo2) + (0.036P)2] where P = (Fo2 + 2Fc2)/3
4971 reflections(Δ/σ)max < 0.001
361 parametersΔρmax = 0.13 e Å3
0 restraintsΔρmin = −0.21 e Å3

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*/Ueq
O41.3508 (2)0.39839 (7)0.26199 (13)0.0562 (5)
O10.9879 (2)0.43838 (7)0.17323 (12)0.0553 (5)
N10.4540 (3)0.59046 (10)0.10343 (16)0.0583 (7)
C251.0230 (4)0.40498 (9)0.44518 (18)0.0446 (7)
C81.0031 (3)0.36017 (9)0.27505 (17)0.0397 (6)
C241.1008 (3)0.39169 (9)0.35680 (17)0.0399 (6)
C110.8489 (4)0.47360 (10)0.15533 (17)0.0448 (7)
C171.2690 (4)0.40833 (9)0.34837 (19)0.0448 (7)
C230.8491 (4)0.39068 (10)0.46109 (19)0.0529 (7)
H23A0.77970.37200.41180.063*
C120.6795 (4)0.46179 (10)0.17407 (18)0.0535 (7)
H12A0.65270.42790.19800.064*
C71.0293 (4)0.27455 (11)0.37128 (19)0.0553 (8)
H7A1.07820.29310.42730.066*
O30.4934 (3)0.63407 (8)0.07056 (14)0.0734 (6)
C90.9767 (3)0.30318 (10)0.28363 (18)0.0445 (7)
C140.5925 (4)0.54981 (11)0.12233 (18)0.0479 (7)
C30.8464 (4)0.30174 (12)0.1116 (2)0.0641 (8)
H3A0.79370.28280.05700.077*
C10.9496 (3)0.38393 (10)0.18595 (19)0.0467 (7)
C271.3749 (3)0.34527 (11)0.23632 (19)0.0462 (7)
N21.4260 (4)0.18672 (11)0.1414 (2)0.0768 (8)
C150.7607 (4)0.56203 (11)0.10407 (18)0.0558 (8)
H15A0.78720.59610.08080.067*
C20.8700 (4)0.35544 (12)0.10426 (19)0.0608 (8)
H2A0.83360.37330.04520.073*
C220.7803 (4)0.40373 (11)0.5478 (2)0.0671 (9)
H22A0.66550.39370.55710.081*
C321.4198 (3)0.30571 (11)0.30582 (19)0.0531 (7)
H32A1.43690.31430.37320.064*
O20.3041 (3)0.57870 (8)0.12092 (16)0.0825 (7)
C100.9002 (4)0.27407 (11)0.2002 (2)0.0526 (7)
C160.8915 (4)0.52370 (11)0.12019 (17)0.0540 (7)
H16A1.00660.53150.10760.065*
C261.1244 (4)0.43468 (10)0.52074 (19)0.0528 (7)
C181.3671 (4)0.43793 (10)0.4217 (2)0.0601 (8)
H18A1.48070.44910.41220.072*
C130.5496 (4)0.50002 (11)0.15740 (19)0.0578 (8)
H13A0.43430.49230.16960.069*
C311.4392 (4)0.25318 (11)0.27459 (19)0.0539 (7)
H31A1.46980.22590.32030.065*
C191.2974 (4)0.45038 (11)0.5068 (2)0.0663 (9)
H19A1.36420.46950.55640.080*
C301.4125 (4)0.24221 (11)0.1749 (2)0.0527 (7)
C40.8843 (4)0.21737 (12)0.2078 (2)0.0721 (9)
H4A0.83630.19780.15290.086*
O51.4527 (3)0.15122 (9)0.20191 (16)0.0954 (8)
C201.0481 (5)0.44692 (12)0.6088 (2)0.0767 (10)
H20A1.11410.46580.65910.092*
C291.3761 (4)0.28167 (12)0.10560 (19)0.0634 (8)
H29A1.36430.27330.03810.076*
C281.3571 (3)0.33380 (11)0.13642 (19)0.0564 (8)
H28A1.33230.36110.09000.068*
C50.9374 (5)0.19142 (12)0.2932 (3)0.0820 (10)
H5A0.92560.15420.29690.098*
O61.4102 (4)0.17823 (9)0.05245 (17)0.1275 (11)
C61.0096 (4)0.22003 (12)0.3755 (2)0.0680 (9)
H6A1.04510.20180.43440.082*
C210.8817 (5)0.43195 (13)0.6221 (2)0.0774 (11)
H21A0.83470.44050.68110.093*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O40.0586 (14)0.0454 (12)0.0676 (12)−0.0072 (9)0.0207 (10)0.0062 (10)
O10.0477 (13)0.0515 (12)0.0657 (12)−0.0035 (10)0.0005 (10)0.0137 (10)
N10.0579 (19)0.0617 (18)0.0550 (15)0.0040 (15)0.0045 (14)0.0064 (14)
C250.0507 (19)0.0348 (15)0.0473 (16)0.0051 (13)0.0006 (14)0.0039 (13)
C80.0376 (17)0.0417 (16)0.0406 (15)−0.0034 (12)0.0087 (12)−0.0034 (13)
C240.0422 (18)0.0337 (15)0.0429 (15)−0.0030 (12)−0.0007 (13)0.0037 (12)
C110.0453 (19)0.0494 (17)0.0387 (15)−0.0052 (14)−0.0014 (13)0.0036 (13)
C170.0462 (19)0.0353 (15)0.0519 (17)−0.0057 (13)−0.0001 (15)0.0033 (13)
C230.055 (2)0.0523 (18)0.0518 (17)0.0060 (14)0.0094 (15)0.0038 (14)
C120.050 (2)0.0451 (18)0.0666 (19)−0.0043 (15)0.0126 (16)0.0111 (15)
C70.060 (2)0.0493 (18)0.0572 (18)−0.0070 (15)0.0095 (15)0.0004 (15)
O30.0901 (18)0.0586 (14)0.0727 (13)0.0070 (12)0.0136 (12)0.0199 (12)
C90.0418 (18)0.0441 (17)0.0490 (16)−0.0071 (13)0.0113 (13)−0.0053 (14)
C140.049 (2)0.0480 (18)0.0461 (16)−0.0017 (15)0.0038 (14)0.0031 (14)
C30.058 (2)0.077 (2)0.0542 (19)−0.0067 (18)−0.0057 (16)−0.0206 (18)
C10.0399 (18)0.0475 (18)0.0529 (17)−0.0023 (14)0.0056 (14)−0.0026 (15)
C270.0383 (17)0.0463 (18)0.0551 (17)−0.0013 (13)0.0094 (14)0.0056 (15)
N20.093 (2)0.067 (2)0.0689 (19)0.0145 (17)0.0008 (17)−0.0064 (17)
C150.057 (2)0.0519 (18)0.0573 (18)−0.0111 (16)0.0026 (16)0.0150 (15)
C20.055 (2)0.075 (2)0.0502 (17)0.0011 (17)−0.0048 (15)−0.0006 (17)
C220.071 (2)0.069 (2)0.065 (2)0.0214 (18)0.0218 (19)0.0203 (18)
C320.056 (2)0.0562 (19)0.0463 (16)−0.0008 (15)0.0037 (14)0.0003 (15)
O20.0545 (16)0.0778 (16)0.1164 (18)0.0085 (12)0.0148 (14)0.0156 (13)
C100.0457 (19)0.0504 (18)0.0618 (18)−0.0079 (14)0.0058 (15)−0.0147 (16)
C160.0465 (19)0.0599 (19)0.0551 (17)−0.0085 (15)0.0030 (14)0.0144 (15)
C260.072 (2)0.0379 (16)0.0467 (17)0.0052 (15)−0.0054 (16)−0.0045 (14)
C180.051 (2)0.0488 (19)0.079 (2)−0.0140 (15)−0.0049 (17)0.0064 (17)
C130.049 (2)0.0567 (19)0.0702 (19)−0.0057 (16)0.0164 (16)0.0074 (16)
C310.059 (2)0.0557 (19)0.0471 (17)0.0056 (15)0.0070 (14)0.0049 (15)
C190.082 (3)0.0444 (19)0.068 (2)−0.0130 (17)−0.0175 (19)−0.0091 (16)
C300.053 (2)0.0541 (19)0.0516 (17)0.0122 (15)0.0069 (15)−0.0025 (16)
C40.073 (3)0.053 (2)0.089 (2)−0.0150 (17)0.007 (2)−0.0250 (19)
O50.144 (2)0.0593 (15)0.0822 (16)0.0152 (15)0.0077 (15)−0.0012 (13)
C200.117 (3)0.061 (2)0.050 (2)0.012 (2)0.002 (2)−0.0108 (16)
C290.072 (2)0.075 (2)0.0436 (16)0.0157 (18)0.0068 (15)0.0045 (17)
C280.059 (2)0.061 (2)0.0503 (18)0.0101 (16)0.0105 (15)0.0154 (16)
C50.094 (3)0.042 (2)0.111 (3)−0.0168 (19)0.017 (2)−0.007 (2)
O60.220 (3)0.098 (2)0.0606 (14)0.0392 (19)−0.0073 (17)−0.0251 (14)
C60.086 (3)0.048 (2)0.072 (2)−0.0035 (17)0.0167 (19)0.0086 (18)
C210.114 (3)0.072 (2)0.050 (2)0.031 (2)0.022 (2)0.0027 (18)

Geometric parameters (Å, °)

O4—C271.380 (3)N2—O51.205 (3)
O4—C171.398 (3)N2—O61.213 (3)
O1—C111.375 (3)N2—C301.456 (3)
O1—C11.396 (3)C15—C161.378 (3)
N1—O31.218 (2)C15—H15A0.9300
N1—O21.224 (3)C2—H2A0.9300
N1—C141.463 (3)C22—C211.391 (4)
C25—C231.408 (3)C22—H22A0.9300
C25—C261.422 (3)C32—C311.382 (3)
C25—C241.423 (3)C32—H32A0.9300
C8—C11.365 (3)C10—C41.416 (3)
C8—C91.434 (3)C16—H16A0.9300
C8—C241.489 (3)C26—C191.405 (4)
C24—C171.361 (3)C26—C201.408 (3)
C11—C121.371 (3)C18—C191.349 (3)
C11—C161.381 (3)C18—H18A0.9300
C17—C181.389 (3)C13—H13A0.9300
C23—C221.369 (3)C31—C301.368 (3)
C23—H23A0.9300C31—H31A0.9300
C12—C131.373 (3)C19—H19A0.9300
C12—H12A0.9300C30—C291.364 (3)
C7—C61.363 (3)C4—C51.347 (4)
C7—C91.403 (3)C4—H4A0.9300
C7—H7A0.9300C20—C211.350 (4)
C9—C101.413 (3)C20—H20A0.9300
C14—C151.363 (3)C29—C281.371 (3)
C14—C131.374 (3)C29—H29A0.9300
C3—C21.349 (3)C28—H28A0.9300
C3—C101.405 (3)C5—C61.385 (4)
C3—H3A0.9300C5—H5A0.9300
C1—C21.396 (3)C6—H6A0.9300
C27—C281.372 (3)C21—H21A0.9300
C27—C321.377 (3)
C27—O4—C17117.38 (19)C1—C2—H2A120.2
C11—O1—C1118.0 (2)C23—C22—C21120.2 (3)
O3—N1—O2123.4 (3)C23—C22—H22A119.9
O3—N1—C14118.4 (3)C21—C22—H22A119.9
O2—N1—C14118.2 (2)C27—C32—C31119.4 (2)
C23—C25—C26118.2 (3)C27—C32—H32A120.3
C23—C25—C24123.2 (2)C31—C32—H32A120.3
C26—C25—C24118.7 (3)C3—C10—C9119.4 (2)
C1—C8—C9117.7 (2)C3—C10—C4121.8 (3)
C1—C8—C24120.6 (2)C9—C10—C4118.8 (3)
C9—C8—C24121.4 (2)C15—C16—C11119.0 (3)
C17—C24—C25118.3 (2)C15—C16—H16A120.5
C17—C24—C8120.1 (2)C11—C16—H16A120.5
C25—C24—C8121.6 (2)C19—C26—C20121.7 (3)
C12—C11—O1123.6 (2)C19—C26—C25119.7 (3)
C12—C11—C16120.9 (3)C20—C26—C25118.5 (3)
O1—C11—C16115.4 (2)C19—C18—C17119.9 (3)
C24—C17—C18123.0 (3)C19—C18—H18A120.1
C24—C17—O4121.2 (2)C17—C18—H18A120.1
C18—C17—O4115.8 (3)C12—C13—C14119.0 (3)
C22—C23—C25121.2 (3)C12—C13—H13A120.5
C22—C23—H23A119.4C14—C13—H13A120.5
C25—C23—H23A119.4C30—C31—C32118.5 (3)
C11—C12—C13119.9 (2)C30—C31—H31A120.7
C11—C12—H12A120.1C32—C31—H31A120.7
C13—C12—H12A120.1C18—C19—C26120.4 (3)
C6—C7—C9121.0 (3)C18—C19—H19A119.8
C6—C7—H7A119.5C26—C19—H19A119.8
C9—C7—H7A119.5C29—C30—C31122.2 (3)
C7—C9—C10118.2 (2)C29—C30—N2118.8 (3)
C7—C9—C8122.4 (2)C31—C30—N2119.1 (3)
C10—C9—C8119.3 (2)C5—C4—C10121.1 (3)
C15—C14—C13121.5 (3)C5—C4—H4A119.5
C15—C14—N1119.3 (3)C10—C4—H4A119.5
C13—C14—N1119.2 (3)C21—C20—C26121.7 (3)
C2—C3—C10121.0 (3)C21—C20—H20A119.1
C2—C3—H3A119.5C26—C20—H20A119.1
C10—C3—H3A119.5C30—C29—C28119.3 (3)
C8—C1—C2123.0 (2)C30—C29—H29A120.3
C8—C1—O1118.6 (2)C28—C29—H29A120.3
C2—C1—O1118.2 (2)C29—C28—C27119.4 (3)
C28—C27—C32121.0 (3)C29—C28—H28A120.3
C28—C27—O4116.3 (2)C27—C28—H28A120.3
C32—C27—O4122.7 (2)C4—C5—C6120.2 (3)
O5—N2—O6122.5 (3)C4—C5—H5A119.9
O5—N2—C30119.5 (3)C6—C5—H5A119.9
O6—N2—C30118.0 (3)C7—C6—C5120.8 (3)
C14—C15—C16119.7 (3)C7—C6—H6A119.6
C14—C15—H15A120.2C5—C6—H6A119.6
C16—C15—H15A120.2C20—C21—C22120.2 (3)
C3—C2—C1119.5 (3)C20—C21—H21A119.9
C3—C2—H2A120.2C22—C21—H21A119.9
C23—C25—C24—C17178.9 (2)C28—C27—C32—C31−3.0 (4)
C26—C25—C24—C17−0.3 (3)O4—C27—C32—C31179.0 (2)
C23—C25—C24—C8−1.5 (4)C2—C3—C10—C91.4 (4)
C26—C25—C24—C8179.3 (2)C2—C3—C10—C4−176.9 (3)
C1—C8—C24—C17−69.6 (3)C7—C9—C10—C3180.0 (2)
C9—C8—C24—C17104.5 (3)C8—C9—C10—C3−2.0 (4)
C1—C8—C24—C25110.8 (3)C7—C9—C10—C4−1.7 (4)
C9—C8—C24—C25−75.1 (3)C8—C9—C10—C4176.3 (2)
C1—O1—C11—C1217.3 (3)C14—C15—C16—C11−0.4 (4)
C1—O1—C11—C16−165.2 (2)C12—C11—C16—C150.0 (4)
C25—C24—C17—C18−0.5 (4)O1—C11—C16—C15−177.5 (2)
C8—C24—C17—C18179.9 (2)C23—C25—C26—C19−179.0 (2)
C25—C24—C17—O4−177.6 (2)C24—C25—C26—C190.2 (4)
C8—C24—C17—O42.8 (4)C23—C25—C26—C201.9 (4)
C27—O4—C17—C24−62.0 (3)C24—C25—C26—C20−178.9 (2)
C27—O4—C17—C18120.7 (2)C24—C17—C18—C191.4 (4)
C26—C25—C23—C22−1.6 (4)O4—C17—C18—C19178.7 (2)
C24—C25—C23—C22179.2 (2)C11—C12—C13—C14−0.2 (4)
O1—C11—C12—C13177.6 (2)C15—C14—C13—C12−0.2 (4)
C16—C11—C12—C130.3 (4)N1—C14—C13—C12179.3 (2)
C6—C7—C9—C101.0 (4)C27—C32—C31—C30−0.2 (4)
C6—C7—C9—C8−176.9 (2)C17—C18—C19—C26−1.5 (4)
C1—C8—C9—C7179.0 (2)C20—C26—C19—C18179.8 (3)
C24—C8—C9—C74.7 (4)C25—C26—C19—C180.7 (4)
C1—C8—C9—C101.1 (4)C32—C31—C30—C293.3 (4)
C24—C8—C9—C10−173.2 (2)C32—C31—C30—N2−177.7 (2)
O3—N1—C14—C150.9 (4)O5—N2—C30—C29−177.7 (3)
O2—N1—C14—C15−179.6 (2)O6—N2—C30—C292.5 (4)
O3—N1—C14—C13−178.6 (2)O5—N2—C30—C313.3 (4)
O2—N1—C14—C130.9 (4)O6—N2—C30—C31−176.5 (3)
C9—C8—C1—C20.5 (4)C3—C10—C4—C5179.6 (3)
C24—C8—C1—C2174.8 (2)C9—C10—C4—C51.3 (4)
C9—C8—C1—O1−174.5 (2)C19—C26—C20—C21179.8 (3)
C24—C8—C1—O1−0.2 (4)C25—C26—C20—C21−1.1 (4)
C11—O1—C1—C8−117.7 (3)C31—C30—C29—C28−3.2 (4)
C11—O1—C1—C267.0 (3)N2—C30—C29—C28177.8 (3)
C17—O4—C27—C28144.1 (2)C30—C29—C28—C270.0 (4)
C17—O4—C27—C32−37.9 (3)C32—C27—C28—C293.1 (4)
C13—C14—C15—C160.5 (4)O4—C27—C28—C29−178.8 (2)
N1—C14—C15—C16−179.0 (2)C10—C4—C5—C6−0.2 (5)
C10—C3—C2—C10.2 (4)C9—C7—C6—C50.1 (4)
C8—C1—C2—C3−1.2 (4)C4—C5—C6—C7−0.5 (5)
O1—C1—C2—C3173.9 (2)C26—C20—C21—C22−0.1 (5)
C25—C23—C22—C210.5 (4)C23—C22—C21—C200.4 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C16—H16A···O2i0.932.543.425 (3)159.
C32—H32A···O6ii0.932.453.360 (3)165.

Symmetry codes: (i) x+1, y, z; (ii) x, −y+1/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KP2173).

References

  • Bruker (2000). SMART, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Hiroshi, A., Makoto, T., Junya, K., Tetsuo, I., Yasushi, O. & Yasushi, T. (2005). J. Am. Chem. Soc.127, 10474–10475. [PubMed]
  • Minatti, A. & Dötz, K. H. (2005). Tetrahedron Asymmetry, 16, 3256–3267.
  • Periasamy, M., Venkatraman, L. & Thomas, K. R. J. (1997). J. Org. Chem 62, 4302–4306. [PubMed]
  • Pu, L. (1998). Chem. Rev.98, 2405–2494. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography