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Acta Crystallogr Sect E Struct Rep Online. 2008 May 1; 64(Pt 5): o848.
Published online 2008 April 16. doi:  10.1107/S160053680800977X
PMCID: PMC2961254

(2Z,2′Z,4E,4′E)-4,4′-(Cyclo­hexane-1,2-diyldinitrilo)dipent-2-en-2-ol

Abstract

A new tetra­dentate chiral Schiff base ligand, C16H26N2O2, has been synthesized by the reaction of acetyl­acetone with (1R,2R)-(−)-1,2-diamino­cyclo­hexane. Both of the mol­ecules in the asymmetric unit are of the same chirality (R configuration), since the absolute configuration was determined by the starting reagent (1R,2R)-(−)-1,2-diamino­cyclo­hexane. The six-membered cyclo­hexane ring is in a chair conformation, and the substituents are equatorial in the most stable conformation (trans-cyclo­hexyl). At the ring substituents, large conjugated —C=N—CH=C—OH systems exist, resulting from the original ketone converted into the enol form. With H atoms excluded, the atoms of each substituent lie in the same plane. The two mol­ecules in the asymmetric unit have almost the same structure, with slight differences in the torsion angles between the substituents and the cyclo­hexane ring; the corresponding N1—(C—C—C)cyclo­hexa­ne torsion angles are −177.2 (3) and 179.3 (4)° in one mol­ecule and −176.5 (3) and 178.4 (4)° in the other. Two intra­molecular O—H(...)N hydrogen bonds exist in each mol­ecule.

Related literature

For the chemistry of Schiff bases, see: Alemi & Shaabani (2000 [triangle]); Bandini et al. (1999 [triangle], 2000 [triangle]); Belokon et al. (1997 [triangle]); Cozzi (2003 [triangle]); Jiang et al. (1995 [triangle]); Kureshy et al. (2001 [triangle]); Sasaki et al. (1991 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o848-scheme1.jpg

Experimental

Crystal data

  • C16H26N2O2
  • M r = 278.39
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o848-efi1.jpg
  • a = 9.7306 (15) Å
  • b = 14.7003 (17) Å
  • c = 12.760 (2) Å
  • β = 109.927 (8)°
  • V = 1716.0 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 293 (2) K
  • 0.20 × 0.15 × 0.10 mm

Data collection

  • Rigaku SCXmini diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 [triangle]) T min = 0.986, T max = 0.993
  • 15462 measured reflections
  • 3485 independent reflections
  • 2740 reflections with I > 2σ(I)
  • R int = 0.046

Refinement

  • R[F 2 > 2σ(F 2)] = 0.061
  • wR(F 2) = 0.167
  • S = 1.10
  • 3485 reflections
  • 371 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.26 e Å−3
  • Δρmin = −0.20 e Å−3

Data collection: CrystalClear (Rigaku, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; 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/S160053680800977X/kp2164sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680800977X/kp2164Isup2.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

In recent years, research on Schiff bases has intensified because some of them form materials with non-linear optical (NLO) activity (Alemi & Shaabani, 2000) and because some can be used for the asymmetric oxidation of methyl phenyl sulfides (Sasaki et al., 1991). The search for new chiral ligands for asymmetric synthesis is an important task in organic chemistry. Various chiral Schiff bases are widely used in asymmetric reactions (Jiang et al., 1995; Belokon et al., 1997; Bandini et al., 1999, 2000; Kureshy et al., 2001; Cozzi, 2003). Herein, we report the synthesis and crystal structure of a new chiral Schiff base ligand (2Z,2'Z,4E,4'E)-4,4'-(cyclohexane-1,2-diylbis(azan-1-yl-1-ylidene))dipent-2-en-2-ol (Fig. 1).

The two molecules in the asymmetric unit have almost the same structure, with slight differences in the torsion angles between the substituents and the cyclohexane ring; the N—C3—C9—C19 and N3—C3—C10—C17 torsion angles are -177.2 (3) and 179.3 (4)°, respectively, and the N2—C1—C5—C23 and N2—C1—C7—C18 torsion angels are -176.5 (3) and 178.4 (4)Å, respectively.

Experimental

Acetylacetone (2.4 g, 0.024 mol) in 6 ml of chloroform was added dropwise to a solution of chloroform (20 ml) containing (1R, 2R)-(–)-1,2-Diaminocyclohexane (1.14 g, 0.01 mol), which was kept at 0–5°C with vigorous stirring during the reaction. After complete addition which took approximately 30 min, the mixture was stirred for another 1 h at room temperature. After the evaporation of the solvent under reduced pressure, the crude product was recrystallized by slowly evaporating with petroleum ether to yield pale-yellow crystals.

Refinement

Hydroxy and methyl H atoms were placed in calculated positions with O—H = 0.82 and C—H = 0.96 Å, and torsion angles were refined. Other H atoms were placed in calculated positions with C—H = 0.93 to 0.98 Å. In the absence of significant anomalous scattering effects, Friedel pairs were averaged.

Figures

Fig. 1.
A view of the compound with the atomic numbering scheme. Displacement ellipsoids were drawn at the 30% probability level.

Crystal data

C16H26N2O2F000 = 608
Mr = 278.39Dx = 1.078 Mg m3
Monoclinic, P21Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 3495 reflections
a = 9.7306 (15) Åθ = 3.2–27.5º
b = 14.7003 (17) ŵ = 0.07 mm1
c = 12.760 (2) ÅT = 293 (2) K
β = 109.927 (8)ºBlock, yellow
V = 1716.0 (4) Å30.20 × 0.15 × 0.10 mm
Z = 4

Data collection

Rigaku SCXmini diffractometer3485 independent reflections
Radiation source: fine-focus sealed tube2740 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.046
Detector resolution: 13.6612 pixels mm-1θmax = 26.0º
T = 293(2) Kθmin = 3.2º
ω scansh = −11→11
Absorption correction: multi-scan(CrystalClear; Rigaku, 2005)k = −17→18
Tmin = 0.986, Tmax = 0.993l = −15→15
15462 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.062H-atom parameters constrained
wR(F2) = 0.167  w = 1/[σ2(Fo2) + (0.0929P)2 + 0.0509P] where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max < 0.001
3485 reflectionsΔρmax = 0.26 e Å3
371 parametersΔρmin = −0.20 e Å3
1 restraintExtinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.044 (14)

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
N20.2331 (3)0.0705 (2)0.1213 (2)0.0495 (7)
C10.1320 (3)0.1372 (3)0.1382 (3)0.0506 (8)
H10.16800.19810.13000.061*
O40.2711 (3)−0.1020 (2)0.0795 (3)0.0823 (9)
H4A0.2247−0.05430.08510.123*
N10.2625 (3)0.1490 (2)0.3420 (2)0.0581 (8)
N40.8253 (4)0.4606 (3)0.3268 (3)0.0678 (9)
C30.6294 (4)0.5743 (3)0.2561 (3)0.0567 (9)
H30.63340.58360.33310.068*
N30.7255 (3)0.6406 (2)0.2316 (2)0.0569 (7)
C40.3731 (4)0.0815 (2)0.1303 (3)0.0495 (8)
C50.1211 (4)0.1297 (3)0.2550 (3)0.0561 (9)
H50.09120.06770.26540.067*
O10.8023 (4)0.7283 (2)0.0754 (2)0.0768 (9)
H1A0.74300.70050.09600.115*
C7−0.0180 (4)0.1249 (3)0.0491 (3)0.0618 (9)
H7A−0.00980.1339−0.02380.074*
H7B−0.05120.06310.05240.074*
C80.4543 (4)0.0087 (3)0.1148 (3)0.0579 (9)
H80.54990.01980.11830.069*
C90.6805 (4)0.4776 (3)0.2460 (3)0.0614 (10)
H90.68350.46870.17070.074*
C100.4723 (5)0.5893 (3)0.1793 (4)0.0742 (12)
H10A0.44180.65030.19050.089*
H10B0.46770.58430.10240.089*
O30.4543 (4)0.2765 (2)0.4469 (3)0.0909 (10)
H3A0.37500.25460.40250.136*
C120.8823 (4)0.7750 (3)0.1538 (4)0.0634 (10)
O20.9822 (4)0.4545 (4)0.5429 (3)0.1050 (13)
H20.90910.46490.48870.157*
C140.4014 (4)−0.0812 (3)0.0939 (3)0.0618 (9)
C150.8997 (4)0.7595 (3)0.2663 (4)0.0633 (10)
H150.96860.79430.31980.076*
C160.3627 (4)0.0888 (3)0.4013 (3)0.0582 (9)
C170.3679 (5)0.5206 (3)0.2010 (4)0.0783 (12)
H17A0.36460.52980.27540.094*
H17B0.27030.53030.14810.094*
C18−0.1303 (5)0.1907 (4)0.0636 (4)0.0777 (12)
H18A−0.10290.25240.05240.093*
H18B−0.22490.17810.00800.093*
C190.5730 (5)0.4084 (3)0.2667 (4)0.0786 (12)
H19A0.60230.34740.25440.094*
H19B0.57800.41260.34380.094*
C201.0821 (5)0.4578 (4)0.4000 (4)0.0835 (14)
H201.16930.45580.38520.100*
C210.9538 (5)0.4634 (3)0.3102 (4)0.0705 (11)
C220.4950 (5)0.1197 (3)0.4755 (4)0.0684 (11)
H220.56180.07640.51600.082*
C230.0078 (5)0.1962 (4)0.2683 (4)0.0831 (14)
H23A−0.00120.18780.34100.100*
H23B0.04070.25790.26430.100*
C240.8217 (4)0.6967 (3)0.3024 (3)0.0603 (9)
C250.4427 (4)0.1743 (3)0.1572 (4)0.0683 (11)
H25A0.38430.21800.10490.103*
H25B0.53900.17250.15250.103*
H25C0.44890.19140.23130.103*
C260.4153 (5)0.4247 (4)0.1903 (5)0.0848 (14)
H26A0.40740.41320.11360.102*
H26B0.35100.38250.20960.102*
C271.0909 (5)0.4549 (4)0.5141 (4)0.0850 (15)
C280.5353 (5)0.2123 (4)0.4938 (4)0.0819 (13)
C29−0.1412 (5)0.1825 (5)0.1784 (4)0.0909 (15)
H29A−0.17880.12290.18680.109*
H29B−0.20910.22780.18720.109*
C300.3316 (5)−0.0111 (3)0.3878 (4)0.0731 (12)
H30A0.2400−0.02360.39780.110*
H30B0.4082−0.04400.44260.110*
H30C0.3266−0.02990.31450.110*
C310.9560 (6)0.4700 (5)0.1934 (5)0.0945 (16)
H31A0.88640.42810.14630.142*
H31B1.05200.45530.19300.142*
H31C0.93120.53080.16610.142*
C321.2405 (6)0.4531 (6)0.6027 (5)0.130 (3)
H32A1.26340.51230.63570.195*
H32B1.31180.43620.56960.195*
H32C1.24140.40960.65900.195*
C330.5043 (6)−0.1553 (4)0.0876 (5)0.0952 (16)
H33A0.4571−0.19360.02460.143*
H33B0.5312−0.19090.15460.143*
H33C0.5903−0.12890.07950.143*
C340.8432 (7)0.6907 (4)0.4256 (4)0.0946 (17)
H34A0.75240.70360.43670.142*
H34B0.91560.73420.46580.142*
H34C0.87520.63060.45220.142*
C350.6841 (7)0.2341 (6)0.5773 (8)0.155 (4)
H35A0.70440.29760.57310.232*
H35B0.75710.19870.56080.232*
H35C0.68530.21980.65100.232*
C360.9633 (7)0.8527 (5)0.1258 (5)0.113 (2)
H37A1.06640.84470.16330.169*
H37B0.93250.90870.14930.169*
H37C0.94300.85430.04670.169*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N20.0395 (14)0.0525 (16)0.0569 (16)−0.0021 (12)0.0168 (11)−0.0008 (14)
C10.0424 (17)0.0480 (18)0.0581 (19)0.0000 (14)0.0127 (14)−0.0004 (16)
O40.0699 (19)0.0546 (16)0.125 (3)−0.0055 (13)0.0370 (17)−0.0164 (17)
N10.0479 (16)0.072 (2)0.0501 (15)0.0054 (14)0.0112 (12)−0.0002 (15)
N40.0515 (19)0.079 (2)0.071 (2)0.0026 (16)0.0175 (15)0.0169 (19)
C30.058 (2)0.059 (2)0.0495 (19)−0.0100 (17)0.0134 (15)0.0080 (18)
N30.0557 (17)0.0589 (18)0.0532 (16)−0.0140 (14)0.0148 (13)0.0023 (15)
C40.0471 (18)0.0487 (19)0.0525 (18)−0.0034 (15)0.0168 (14)0.0049 (16)
C50.0429 (18)0.067 (2)0.054 (2)0.0012 (16)0.0109 (15)0.0006 (18)
O10.089 (2)0.084 (2)0.0676 (17)−0.0244 (17)0.0395 (16)−0.0090 (16)
C70.052 (2)0.065 (2)0.061 (2)0.0033 (17)0.0101 (16)−0.0034 (19)
C80.0461 (19)0.060 (2)0.068 (2)0.0015 (16)0.0205 (16)0.0025 (18)
C90.054 (2)0.065 (2)0.063 (2)−0.0031 (17)0.0166 (17)0.0076 (19)
C100.057 (2)0.072 (3)0.088 (3)−0.001 (2)0.017 (2)0.016 (2)
O30.079 (2)0.076 (2)0.097 (2)−0.0045 (17)0.0019 (17)−0.0026 (19)
C120.060 (2)0.063 (2)0.076 (3)−0.0123 (18)0.035 (2)−0.008 (2)
O20.067 (2)0.162 (4)0.081 (2)0.006 (2)0.0181 (17)0.045 (2)
C140.059 (2)0.057 (2)0.073 (2)0.0026 (18)0.0268 (18)0.000 (2)
C150.057 (2)0.064 (2)0.065 (2)−0.0159 (18)0.0167 (18)−0.0082 (19)
C160.053 (2)0.071 (2)0.0521 (19)0.0056 (18)0.0207 (16)0.0084 (19)
C170.056 (2)0.087 (3)0.088 (3)−0.012 (2)0.019 (2)0.008 (3)
C180.053 (2)0.084 (3)0.080 (3)0.014 (2)0.0019 (19)−0.008 (2)
C190.067 (3)0.062 (3)0.103 (3)−0.009 (2)0.024 (2)0.007 (3)
C200.055 (3)0.094 (3)0.100 (3)−0.004 (2)0.024 (2)0.019 (3)
C210.058 (2)0.071 (3)0.084 (3)−0.003 (2)0.027 (2)0.012 (2)
C220.056 (2)0.077 (3)0.064 (2)0.0063 (19)0.0089 (18)0.004 (2)
C230.056 (2)0.118 (4)0.074 (3)0.024 (2)0.019 (2)−0.012 (3)
C240.057 (2)0.063 (2)0.055 (2)−0.0027 (17)0.0121 (16)0.0036 (19)
C250.054 (2)0.058 (2)0.092 (3)−0.0115 (18)0.025 (2)0.000 (2)
C260.066 (3)0.079 (3)0.100 (4)−0.020 (2)0.016 (2)0.000 (3)
C270.064 (3)0.095 (4)0.087 (3)−0.009 (2)0.013 (2)0.035 (3)
C280.061 (3)0.085 (3)0.084 (3)−0.004 (2)0.004 (2)0.005 (3)
C290.049 (2)0.123 (4)0.099 (3)0.020 (3)0.023 (2)−0.006 (3)
C300.074 (3)0.069 (3)0.072 (3)0.001 (2)0.018 (2)0.013 (2)
C310.078 (3)0.123 (5)0.090 (3)−0.003 (3)0.040 (3)−0.001 (3)
C320.072 (4)0.190 (8)0.105 (4)−0.031 (4)0.000 (3)0.054 (5)
C330.088 (3)0.071 (3)0.128 (5)0.018 (3)0.038 (3)−0.003 (3)
C340.116 (4)0.101 (4)0.053 (2)−0.037 (3)0.011 (2)−0.001 (3)
C350.096 (5)0.110 (5)0.193 (8)−0.020 (4)−0.037 (5)−0.009 (5)
C360.125 (5)0.114 (5)0.117 (4)−0.048 (4)0.066 (4)−0.001 (4)

Geometric parameters (Å, °)

N2—C41.337 (4)C18—C291.509 (7)
N2—C11.456 (4)C18—H18A0.9700
C1—C71.524 (5)C18—H18B0.9700
C1—C51.533 (5)C19—C261.531 (6)
C1—H10.9800C19—H19A0.9700
O4—C141.256 (5)C19—H19B0.9700
O4—H4A0.8499C20—C211.379 (6)
N1—C161.343 (5)C20—C271.431 (8)
N1—C51.471 (5)C20—H200.9300
N4—C211.338 (5)C21—C311.502 (7)
N4—C91.456 (5)C22—C281.413 (7)
C3—N31.457 (5)C22—H220.9300
C3—C101.524 (5)C23—C291.525 (6)
C3—C91.525 (6)C23—H23A0.9700
C3—H30.9800C23—H23B0.9700
N3—C241.340 (5)C24—C341.516 (6)
C4—C81.385 (5)C25—H25A0.9600
C4—C251.509 (5)C25—H25B0.9600
C5—C231.525 (6)C25—H25C0.9600
C5—H50.9800C26—H26A0.9700
O1—C121.244 (5)C26—H26B0.9700
O1—H1A0.8200C27—C321.508 (7)
C7—C181.517 (6)C28—C351.511 (7)
C7—H7A0.9700C29—H29A0.9700
C7—H7B0.9700C29—H29B0.9700
C8—C141.410 (6)C30—H30A0.9600
C8—H80.9300C30—H30B0.9600
C9—C191.544 (6)C30—H30C0.9600
C9—H90.9800C31—H31A0.9600
C10—C171.523 (6)C31—H31B0.9600
C10—H10A0.9700C31—H31C0.9600
C10—H10B0.9700C32—H32A0.9600
O3—C281.245 (6)C32—H32B0.9600
O3—H3A0.8500C32—H32C0.9600
C12—C151.406 (6)C33—H33A0.9600
C12—C361.498 (7)C33—H33B0.9600
O2—C271.232 (6)C33—H33C0.9600
O2—H20.8200C34—H34A0.9600
C14—C331.501 (6)C34—H34B0.9600
C15—C241.371 (6)C34—H34C0.9600
C15—H150.9300C35—H35A0.9600
C16—C221.389 (6)C35—H35B0.9600
C16—C301.498 (6)C35—H35C0.9600
C17—C261.504 (8)C36—H37A0.9600
C17—H17A0.9700C36—H37B0.9600
C17—H17B0.9700C36—H37C0.9600
C4—N2—C1128.7 (3)C27—C20—H20117.6
N2—C1—C7109.5 (3)N4—C21—C20119.8 (4)
N2—C1—C5111.7 (3)N4—C21—C31119.3 (4)
C7—C1—C5110.5 (3)C20—C21—C31120.8 (4)
N2—C1—H1108.4C16—C22—C28124.6 (4)
C7—C1—H1108.4C16—C22—H22117.7
C5—C1—H1108.4C28—C22—H22117.7
C14—O4—H4A109.0C29—C23—C5111.7 (4)
C16—N1—C5127.7 (4)C29—C23—H23A109.3
C21—N4—C9127.8 (4)C5—C23—H23A109.3
N3—C3—C10110.0 (3)C29—C23—H23B109.3
N3—C3—C9110.7 (3)C5—C23—H23B109.3
C10—C3—C9111.4 (3)H23A—C23—H23B107.9
N3—C3—H3108.2N3—C24—C15121.9 (3)
C10—C3—H3108.2N3—C24—C34118.8 (4)
C9—C3—H3108.2C15—C24—C34119.3 (4)
C24—N3—C3128.2 (3)C4—C25—H25A109.5
N2—C4—C8120.6 (3)C4—C25—H25B109.5
N2—C4—C25119.6 (3)H25A—C25—H25B109.5
C8—C4—C25119.8 (3)C4—C25—H25C109.5
N1—C5—C23108.5 (3)H25A—C25—H25C109.5
N1—C5—C1111.3 (3)H25B—C25—H25C109.5
C23—C5—C1110.7 (3)C17—C26—C19111.1 (4)
N1—C5—H5108.7C17—C26—H26A109.4
C23—C5—H5108.7C19—C26—H26A109.4
C1—C5—H5108.7C17—C26—H26B109.4
C12—O1—H1A109.5C19—C26—H26B109.4
C18—C7—C1112.3 (3)H26A—C26—H26B108.0
C18—C7—H7A109.1O2—C27—C20123.0 (4)
C1—C7—H7A109.1O2—C27—C32119.0 (5)
C18—C7—H7B109.1C20—C27—C32118.1 (5)
C1—C7—H7B109.1O3—C28—C22123.8 (4)
H7A—C7—H7B107.9O3—C28—C35118.4 (5)
C4—C8—C14124.2 (3)C22—C28—C35117.8 (5)
C4—C8—H8117.9C18—C29—C23110.8 (4)
C14—C8—H8117.9C18—C29—H29A109.5
N4—C9—C3111.4 (3)C23—C29—H29A109.5
N4—C9—C19108.3 (3)C18—C29—H29B109.5
C3—C9—C19109.9 (3)C23—C29—H29B109.5
N4—C9—H9109.1H29A—C29—H29B108.1
C3—C9—H9109.1C16—C30—H30A109.5
C19—C9—H9109.1C16—C30—H30B109.5
C17—C10—C3111.9 (4)H30A—C30—H30B109.5
C17—C10—H10A109.2C16—C30—H30C109.5
C3—C10—H10A109.2H30A—C30—H30C109.5
C17—C10—H10B109.2H30B—C30—H30C109.5
C3—C10—H10B109.2C21—C31—H31A109.5
H10A—C10—H10B107.9C21—C31—H31B109.5
C28—O3—H3A108.4H31A—C31—H31B109.5
O1—C12—C15123.8 (4)C21—C31—H31C109.5
O1—C12—C36117.7 (4)H31A—C31—H31C109.5
C15—C12—C36118.5 (4)H31B—C31—H31C109.5
C27—O2—H2109.5C27—C32—H32A109.5
O4—C14—C8122.8 (4)C27—C32—H32B109.5
O4—C14—C33118.3 (4)H32A—C32—H32B109.5
C8—C14—C33118.9 (4)C27—C32—H32C109.5
C24—C15—C12124.3 (4)H32A—C32—H32C109.5
C24—C15—H15117.8H32B—C32—H32C109.5
C12—C15—H15117.8C14—C33—H33A109.5
N1—C16—C22119.6 (4)C14—C33—H33B109.5
N1—C16—C30120.1 (4)H33A—C33—H33B109.5
C22—C16—C30120.2 (4)C14—C33—H33C109.5
C26—C17—C10111.2 (4)H33A—C33—H33C109.5
C26—C17—H17A109.4H33B—C33—H33C109.5
C10—C17—H17A109.4C24—C34—H34A109.5
C26—C17—H17B109.4C24—C34—H34B109.5
C10—C17—H17B109.4H34A—C34—H34B109.5
H17A—C17—H17B108.0C24—C34—H34C109.5
C29—C18—C7111.1 (4)H34A—C34—H34C109.5
C29—C18—H18A109.4H34B—C34—H34C109.5
C7—C18—H18A109.4C28—C35—H35A109.5
C29—C18—H18B109.4C28—C35—H35B109.5
C7—C18—H18B109.4H35A—C35—H35B109.5
H18A—C18—H18B108.0C28—C35—H35C109.5
C26—C19—C9112.3 (4)H35A—C35—H35C109.5
C26—C19—H19A109.1H35B—C35—H35C109.5
C9—C19—H19A109.1C12—C36—H37A109.5
C26—C19—H19B109.1C12—C36—H37B109.5
C9—C19—H19B109.1H37A—C36—H37B109.5
H19A—C19—H19B107.9C12—C36—H37C109.5
C21—C20—C27124.7 (4)H37A—C36—H37C109.5
C21—C20—H20117.6H37B—C36—H37C109.5
C4—N2—C1—C7139.4 (4)C36—C12—C15—C24173.5 (5)
C4—N2—C1—C5−97.9 (4)C5—N1—C16—C22175.8 (4)
C10—C3—N3—C24127.5 (4)C5—N1—C16—C30−4.5 (6)
C9—C3—N3—C24−108.9 (4)C3—C10—C17—C26−56.1 (6)
C1—N2—C4—C8177.7 (3)C1—C7—C18—C29−55.9 (5)
C1—N2—C4—C25−2.6 (6)N4—C9—C19—C26176.4 (4)
C16—N1—C5—C23140.5 (4)C3—C9—C19—C2654.5 (5)
C16—N1—C5—C1−97.5 (4)C9—N4—C21—C20171.0 (4)
N2—C1—C5—N162.6 (4)C9—N4—C21—C31−10.7 (7)
C7—C1—C5—N1−175.3 (3)C27—C20—C21—N4−4.3 (8)
N2—C1—C5—C23−176.5 (3)C27—C20—C21—C31177.5 (5)
C7—C1—C5—C23−54.5 (4)N1—C16—C22—C28−0.7 (7)
N2—C1—C7—C18178.4 (4)C30—C16—C22—C28179.7 (5)
C5—C1—C7—C1855.1 (5)N1—C5—C23—C29178.1 (4)
N2—C4—C8—C14−3.0 (6)C1—C5—C23—C2955.7 (5)
C25—C4—C8—C14177.3 (4)C3—N3—C24—C15−176.3 (4)
C21—N4—C9—C3−98.6 (5)C3—N3—C24—C343.1 (7)
C21—N4—C9—C19140.5 (5)C12—C15—C24—N33.4 (7)
N3—C3—C9—N462.7 (4)C12—C15—C24—C34−175.9 (5)
C10—C3—C9—N4−174.6 (3)C10—C17—C26—C1955.1 (6)
N3—C3—C9—C19−177.2 (3)C9—C19—C26—C17−55.2 (6)
C10—C3—C9—C19−54.5 (4)C21—C20—C27—O22.2 (9)
N3—C3—C10—C17179.3 (4)C21—C20—C27—C32−177.3 (6)
C9—C3—C10—C1756.1 (5)C16—C22—C28—O31.8 (9)
C4—C8—C14—O45.3 (7)C16—C22—C28—C35−179.7 (6)
C4—C8—C14—C33−175.1 (4)C7—C18—C29—C2355.6 (6)
O1—C12—C15—C24−5.8 (7)C5—C23—C29—C18−56.3 (6)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O4—H4A···N20.851.892.644 (4)147
O1—H1A···N30.822.002.684 (4)141
O3—H3A···N10.851.902.662 (5)148
O2—H2···N40.821.952.659 (5)145

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KP2164).

References

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