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Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): o285–o286.
Published online 2010 January 9. doi:  10.1107/S1600536809055561
PMCID: PMC2979705

2-[(Cyclo­penta-1,3-dien-2-yl)diphenyl­meth­yl]-1-methyl-1H-imidazole

Abstract

The title compound, C22H20N2, (Ib), forms along with 2-[(cyclo­penta-1,3-dien-1-yl)diphenyl­meth­yl]-1-methyl-1H-imid­azole, (Ia), which differs with respect to the position of the double-bonds in the C5H5 ring, in an approximately 3:7 ratio (Ia:Ib; NMR spectroscopy data). However, in a single crystal, only compound (Ib) is present. H atoms of the CH2 group (C5H5 ring) were found from the difference Fourier synthesis and refined isotropically using the riding model. Hypothesis on possible presence of the (Ia) isomer in crystal lattice (model with a C5H5 ring disordered between two positions) was especially checked and rejected due to its inconsistency. In the crystal structure, no significant hydrogen-bonding inter­actions between the CH2 groups of the C5H5 rings and nonsubstituted N-atoms of the imidazole rings were observed. Despite the fact that the chemically achiral compound (I) crystallizes in a chiral space group P212121, neither the absolute structure determination nor assignment of the inversion twinning was possible in the absence of a heavy atom.

Related literature

For the structural parameters of mono-alkyl substituted cyclo­penta­dienes (organic structures only), see: Tacke et al. (2001 [triangle]); Liebling & Marsh (1965 [triangle]); Haumann et al.(1996 [triangle]); Deck et al. (2004 [triangle]); Malpass et al. (2004 [triangle]); Cheung et al. (2005 [triangle]); Bauer et al. (2001 [triangle]); Huerlander et al. (2002 [triangle]); Millelr & Bercaw (2004 [triangle]); Li et al. (2005 [triangle]); Brunner et al. (2004 [triangle]); Otero et al. (2007 [triangle]); Hutton et al. (2008 [triangle]). For the structural parameters of 1,2-dialkyl-1H-imidazoles (organic structures only, not bi- or oligocyclic, non-ionic), see: Bruijnincx et al. (2005 [triangle]); Aakeroy et al. (2006 [triangle]); Zhang et al. (2007 [triangle]); Upadhyaya et al. (1997 [triangle]); Braussaud et al. (2001 [triangle]); Peters et al. (2005 [triangle]); Laus et al. (2008 [triangle]). For the structural parameters of Li, Ti, and Zr complexes derived from 1H-imidazol(in)-2-yl side-chain-functionalized cyclo­penta­dienes, see: Krut’ko et al. (2006 [triangle]); Nie et al. (2008 [triangle]); Wang et al. (2009 [triangle]). For a description of the Cambridge Structural database, see: Allen (2002 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o285-scheme1.jpg

Experimental

Crystal data

  • C22H20N2
  • M r = 312.40
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o285-efi1.jpg
  • a = 10.563 (5) Å
  • b = 10.603 (5) Å
  • c = 15.185 (7) Å
  • V = 1700.6 (14) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 295 K
  • 0.20 × 0.05 × 0.05 mm

Data collection

  • Bruker SMART APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.986, T max = 0.996
  • 8785 measured reflections
  • 1922 independent reflections
  • 1543 reflections with I > 2σ(I)
  • R int = 0.033

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.120
  • S = 1.04
  • 1922 reflections
  • 218 parameters
  • 5 restraints
  • H-atom parameters constrained
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.11 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [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]) and OLEX2 (Dolomanov et al., 2009 [triangle]); software used to prepare material for publication: SHELXTL and OLEX2.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809055561/dn2523sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809055561/dn2523Isup2.hkl

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

Acknowledgments

Financial support from the National Natural Science Foundation of China (project No. 20702041), Shaanxi Provincial Department of Education (grants Nos. 09 J K733 and 07 J K393), Shaanxi Administration of Foreign Expert Affairs (grant No. 20096100097), and Shaanxi Provincial Department of Science and Technology (grant No. 2007B05) is gratefully acknowledged. The authors are thankful to Mr Sun Wei for his help in measuring the NMR spectra. MVB is especially grateful to his former co-author and old friend, Dr Andrei V. Churakov, for his invaluable advice during the preparation of this contribution.

supplementary crystallographic information

Comment

1H-Imidazol(in)-2-yl side-chain functionalized cyclopentadienes were introduced as ligands into the organometallic chemistry, and, particularly into that of the Group 4 transition metals, not long ago (Krut'ko et al., 2006; Nie et al., 2008; Wang et al., 2009). This contribution reports the first structural characterization of a ligand of question in its CH-acid form.

The title compound, C22H20N2, (I), presents a mixture of two isomers on the substituent position in respect to the double bond system in the C5H5-ring, 2-[(cyclopenta-1,3-dien-1-yl]diphenylmethyl]-1-methyl-1H-imidazole, (Ia), and 2-[(cyclopenta-1,3-dien-2-yl]diphenylmethyl]-1-methyl-1H-imidazole, (Ib), what are formed in an approximately 3: 7 ratio. However, in a single-crystal, only compound (Ib) is present. H-atoms of the CH2-group (C5H5-ring) were found from the difference Fourier synthesis and refined isotropically using the riding model. Hypothesis on possible presence of the (Ia) isomer in crystal lattice (model with a C5H5-ring disordered between two positions) was especially checked and rejected due to its inconsistency. The Cp-ring is planar within 0.004 Å, with the bridging carbon C5 deviating from the r.m.s. C11 through C15 plane by 0.084 (4) Å. As for the rest of the molecule, all the bond lengths and angles are within normal ranges (see Related literature section). Both phenyl rings C21 through C26 and C31 through C36 are planar within 0.02 Å. The imidazole moiety C1/N1/C2/C3/N2/ is planar within 0.005 Å, with atoms C4 (1-methyl group) and C5 (bridging carbon atom) deviating from the imidazole ring plane by 0.091 (5) and 0.021 (4) Å, respectively. No special intermolecular contacts in the crystal lattice were observed. Despite the fact that a chemically achiral compound (I) crystallizes in a chiral space group P212121, neither the absolute structure determination nor approval of the inversion twinning was possible due to evident reasons (Mo-Kα radiation with no atoms heavier than nitrogen).

Experimental

All operations were performed on an Ar-vacuum line using the conventional Schlenk technique. — NMR spectra were recorded on Varian INOVA-400 instrument in CDCl3 at 298 K. For 1H and 13C{1H} spectra, the TMS resonances (δH = 0.0 and δC = 0.0) were used as internal reference standards. — Chromato-mass spectrum was measured on Agilent 6890 Series GC system equipped with HP 5973 mass-selective detector. — The elemental analysis was performed on the Vario ELIII CHNOS automated analyzer.

To a solution of 1-methyl-1H-imidazole (1.23 g, 15.0 mmol) in tetrahydrofuran (THF; 60 ml), a solution of n-BuLi in hexane (8.3 ml, 1.82 M, 15.1 mmol) was added under stirring at 195 K (acetone bath) during 30 min. The reaction mixture was stirred at the same temperature for additional 45 min, that gave a bright-yellow solution. To this slurry, a solution of 6,6-diphenylfulvene (3.45 g, 15.0 mmol) in THF (45 ml) was added dropwise during 30 min. The color of the reaction mixture turned brown. The reaction mixture was allowed to warm up gradually up to ambient temperature and the stirring was continued for the next 12 h. The mixture was quenched with water (50 ml; ice-bath cooling), the organic phase was separated, the water phase was extracted with CH2Cl2 (3 × 30 ml), and the combined extracts were dried with Na2SO4. Concentrating of the organic extracts on a rotary evaporator gave crude (I) as a brown solid. Crude (I) was refluxed with Et2O (10 ml) cooled down to room temperature and the filtered-off solid was recrystallized from CH2Cl2 – Et2O mixture (1.8: 10) that gave pure (I) as yellowish crystals. Yield 1.6 g, (34%). — 1H NMR: δ = 2.92 (s, 3 H, NCH3, a), 2.96 (s, 3 H, NCH3, b), 3.05 (m, 2 H, CH2 in Cp, b), 3.10 (m, 2 H, CH2 in Cp, a), 5.91, 6.05, 6.27, 6.28, 6.37, 6.38 (all m, all 1 H in respective ratios, CH in Cp, a,b), 6.84, 7.07 (both d, 1 H + 1 H, 3JHH = 1.22 Hz, CH=CH in imidazole, b), 6.85, 7.06 (both d, 1 H + 1 H, 3JHH = 1.22 Hz, CH=CH in imidazole, a), 7.21–7.32 (m, 10 H in respect to the sum of the relative integral intensities for a and b, CH in Ph, a,b). Molar ratio a: b equals to 3: 7. — 13C{1H} NMR: δ = 34.75 (NCH3, b), 34.90 (NCH3, a), 40.32 (CH2 in Cp, b), 43.85 (CH2 in Cp, a), 57.14 (CPh2, b), 58.02 (CPh2, a), 122.31, 126.63 (CH=CH in imidazole, a,b), 126.43 (p-CH in Ph, a), 126.51 (p-CH in Ph, b), 127.73, 129.38 (o- and m-CH in Ph, b), 127.79, 129.16 (o- and m-CH in Ph, a), 128.76, 131.98, 135.94 (CH in Cp, b), 130.58, 130.91, 134.00 (CH in Cp, a), 142.67 (ipso-C in Ph, b), 143.32 (ipso-C in Ph, a), 150.14 (N—C=N, b), 150.67 (N—C=N, a), 150.60 (C in Cp, b), 153.13 (C in Cp, a). — EI MS (70 eV) m/z (%): 312 (100) [M], 311 (66) [M – H], 297 (3) [M – CH3], 285 (34) [M – HCN], 247 (9) [M – C5H5], 235 (72) [M – Ph].— Anal. Found: C, 83.81; H, 6.35; N, 8.76%. C22H20N2 Calc.: C, 84.58; H, 6.45; N, 8.97%. Single crystal of (I) suitable for X-ray diffraction analysis was obtained by crystallization of (I) from CH2Cl2 – Et2O mixture (1: 6 vol.)

Refinement

Non-H atoms were refined anisotropically. H atoms were treated as riding atoms with distances C—H = 0.96 (CH3), 0.97 (CH2), 0.93 Å (CArH), and Uiso(H) = 1.5 Ueq(C), 1.2 Ueq(C), and 1.2 Ueq(C), respectively. The components of the anisotropic displacement parameters (ADP-s) for C12 through C15-atoms of the C5H4-group along 1,2- and 1,3-directions were restrained to be the same with su of 0.002 Å2 (DELU instruction). Despite the fact that an achiral compound (I) crystallizes in a chiral space group P212121, neither the absolute structure determination nor approval of the inversion twinning was possible due to evident reasons (Mo-Kα radiation with no atoms heavier than nitrogen). Thus, the Friedel opposites were merged and treated as equivalents.

Figures

Fig. 1.
A view of the molecule of compound (I). Displacement ellipsoids are shown at the 50% probability level. All H-atoms except of those in the C5H5-ring are omitted for clarity.
Fig. 2.
Isomers (Ia) and (Ib).

Crystal data

C22H20N2F(000) = 664
Mr = 312.40Dx = 1.220 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 5639 reflections
a = 10.563 (5) Åθ = 2.3–28.0°
b = 10.603 (5) ŵ = 0.07 mm1
c = 15.185 (7) ÅT = 295 K
V = 1700.6 (14) Å3Prism, colorless
Z = 40.20 × 0.05 × 0.05 mm

Data collection

Bruker SMART APEXII diffractometer1922 independent reflections
Radiation source: fine-focus sealed tube1543 reflections with I > 2σ(I)
graphiteRint = 0.033
Detector resolution: 8.333 pixels mm-1θmax = 26.0°, θmin = 2.3°
phi and ω scansh = −12→13
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)k = −13→13
Tmin = 0.986, Tmax = 0.996l = −10→18
8785 measured reflections

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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0736P)2 + 0.110P] where P = (Fo2 + 2Fc2)/3
1922 reflections(Δ/σ)max < 0.001
218 parametersΔρmax = 0.27 e Å3
5 restraintsΔρmin = −0.11 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
N10.1464 (2)0.6352 (2)0.49551 (13)0.0578 (6)
N20.2989 (2)0.73895 (18)0.56444 (14)0.0588 (6)
C10.2381 (2)0.6304 (2)0.55926 (15)0.0460 (5)
C20.1512 (3)0.7552 (3)0.4606 (2)0.0725 (8)
H20.09960.78760.41640.087*
C30.2442 (3)0.8160 (3)0.5025 (2)0.0756 (9)
H30.26850.89870.49140.091*
C40.0623 (3)0.5371 (3)0.4627 (2)0.0785 (9)
H4C0.02740.49120.51150.118*
H4A0.10910.48050.42560.118*
H4B−0.00500.57490.42940.118*
C50.2651 (2)0.5151 (2)0.61653 (14)0.0412 (5)
C110.3890 (2)0.5365 (2)0.66661 (15)0.0457 (5)
C120.4947 (2)0.4661 (3)0.66347 (17)0.0561 (6)
H120.50630.39690.62670.067*
C130.5894 (3)0.5134 (3)0.7259 (2)0.0778 (8)
H13A0.66560.53950.69540.093*
H13B0.61130.44890.76860.093*
C140.5283 (3)0.6217 (3)0.76939 (19)0.0790 (8)
H140.56410.67190.81300.095*
C150.4055 (3)0.6363 (2)0.73309 (18)0.0616 (6)
H150.34640.69740.74840.074*
C210.1592 (2)0.4951 (2)0.68599 (14)0.0443 (5)
C220.0450 (2)0.5593 (3)0.68353 (18)0.0580 (7)
H220.03120.62080.64090.070*
C23−0.0488 (3)0.5321 (3)0.7443 (2)0.0754 (9)
H23−0.12530.57540.74200.090*
C24−0.0307 (3)0.4438 (3)0.8067 (2)0.0807 (10)
H24−0.09590.42370.84530.097*
C250.0844 (3)0.3828 (3)0.81354 (18)0.0688 (8)
H250.09800.32460.85840.083*
C260.1786 (3)0.4083 (2)0.75399 (16)0.0562 (6)
H260.25620.36750.75890.067*
C310.2772 (2)0.3977 (2)0.55630 (14)0.0430 (5)
C320.3568 (2)0.4048 (2)0.48296 (16)0.0537 (6)
H320.40360.47770.47280.064*
C330.3665 (3)0.3046 (3)0.42553 (18)0.0650 (7)
H330.41880.31120.37650.078*
C340.3004 (3)0.1959 (3)0.4395 (2)0.0713 (8)
H340.30820.12880.40040.086*
C350.2234 (3)0.1862 (3)0.5106 (2)0.0707 (8)
H350.17850.11200.52040.085*
C360.2110 (2)0.2860 (2)0.56874 (17)0.0536 (6)
H360.15750.27800.61700.064*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0615 (14)0.0586 (12)0.0533 (11)0.0116 (11)−0.0076 (11)0.0052 (11)
N20.0645 (14)0.0426 (10)0.0692 (13)−0.0012 (10)0.0033 (12)0.0092 (10)
C10.0457 (13)0.0445 (12)0.0479 (11)0.0063 (11)0.0039 (10)0.0027 (10)
C20.085 (2)0.0667 (17)0.0661 (16)0.0255 (17)−0.0024 (17)0.0166 (16)
C30.090 (2)0.0497 (14)0.087 (2)0.0101 (16)0.0023 (19)0.0205 (15)
C40.073 (2)0.082 (2)0.0800 (19)0.0081 (17)−0.0301 (17)−0.0082 (18)
C50.0389 (11)0.0402 (11)0.0445 (11)0.0008 (10)0.0002 (9)0.0015 (9)
C110.0440 (12)0.0439 (12)0.0491 (12)−0.0060 (10)0.0033 (10)0.0054 (11)
C120.0452 (13)0.0594 (14)0.0638 (14)0.0000 (12)−0.0020 (11)−0.0009 (12)
C130.0457 (13)0.103 (2)0.0843 (19)−0.0100 (13)−0.0138 (13)0.0156 (17)
C140.0928 (19)0.0814 (18)0.0630 (16)−0.0413 (15)−0.0177 (15)0.0016 (14)
C150.0736 (15)0.0530 (13)0.0584 (14)−0.0067 (13)0.0016 (13)−0.0091 (14)
C210.0438 (12)0.0425 (11)0.0467 (11)−0.0046 (10)0.0029 (10)−0.0078 (11)
C220.0454 (13)0.0666 (16)0.0621 (15)0.0010 (12)0.0014 (12)−0.0066 (15)
C230.0467 (14)0.095 (2)0.085 (2)−0.0048 (15)0.0135 (15)−0.017 (2)
C240.073 (2)0.092 (2)0.077 (2)−0.0333 (19)0.0245 (18)−0.0198 (19)
C250.083 (2)0.0648 (17)0.0583 (15)−0.0207 (16)0.0146 (15)0.0004 (14)
C260.0612 (15)0.0536 (13)0.0539 (13)−0.0056 (12)0.0048 (12)−0.0029 (12)
C310.0394 (11)0.0423 (11)0.0474 (11)0.0039 (10)−0.0033 (10)−0.0012 (9)
C320.0508 (14)0.0553 (13)0.0552 (13)0.0013 (12)0.0043 (12)−0.0002 (12)
C330.0619 (16)0.0782 (18)0.0550 (14)0.0102 (15)0.0035 (13)−0.0121 (15)
C340.0768 (19)0.0639 (17)0.0734 (18)0.0084 (16)−0.0021 (16)−0.0177 (16)
C350.081 (2)0.0531 (14)0.0779 (18)−0.0053 (15)−0.0032 (18)−0.0113 (14)
C360.0538 (14)0.0488 (13)0.0583 (14)−0.0027 (11)0.0019 (13)−0.0059 (11)

Geometric parameters (Å, °)

N1—C11.370 (3)C15—H150.9300
N1—C21.380 (3)C21—C221.386 (3)
N1—C41.456 (4)C21—C261.398 (3)
N2—C11.321 (3)C22—C231.384 (4)
N2—C31.373 (3)C22—H220.9300
C1—C51.527 (3)C23—C241.346 (5)
C2—C31.336 (4)C23—H230.9300
C2—H20.9300C24—C251.381 (5)
C3—H30.9300C24—H240.9300
C4—H4C0.9600C25—C261.372 (4)
C4—H4A0.9600C25—H250.9300
C4—H4B0.9600C26—H260.9300
C5—C111.530 (3)C31—C361.388 (3)
C5—C311.550 (3)C31—C321.398 (3)
C5—C211.552 (3)C32—C331.378 (3)
C11—C121.344 (3)C32—H320.9300
C11—C151.473 (3)C33—C341.364 (4)
C12—C131.466 (4)C33—H330.9300
C12—H120.9300C34—C351.357 (4)
C13—C141.474 (5)C34—H340.9300
C13—H13A0.9700C35—C361.384 (4)
C13—H13B0.9700C35—H350.9300
C14—C151.417 (4)C36—H360.9300
C14—H140.9300
C1—N1—C2106.3 (2)C14—C15—C11107.3 (3)
C1—N1—C4130.2 (2)C14—C15—H15126.4
C2—N1—C4123.4 (2)C11—C15—H15126.4
C1—N2—C3105.8 (2)C22—C21—C26118.1 (2)
N2—C1—N1110.7 (2)C22—C21—C5122.9 (2)
N2—C1—C5124.9 (2)C26—C21—C5119.1 (2)
N1—C1—C5124.4 (2)C23—C22—C21120.2 (3)
C3—C2—N1106.8 (3)C23—C22—H22119.9
C3—C2—H2126.6C21—C22—H22119.9
N1—C2—H2126.6C24—C23—C22120.8 (3)
C2—C3—N2110.5 (3)C24—C23—H23119.6
C2—C3—H3124.8C22—C23—H23119.6
N2—C3—H3124.8C23—C24—C25120.3 (3)
N1—C4—H4C109.5C23—C24—H24119.8
N1—C4—H4A109.5C25—C24—H24119.8
H4C—C4—H4A109.5C26—C25—C24119.8 (3)
N1—C4—H4B109.5C26—C25—H25120.1
H4C—C4—H4B109.5C24—C25—H25120.1
H4A—C4—H4B109.5C25—C26—C21120.7 (3)
C1—C5—C11108.92 (18)C25—C26—H26119.7
C1—C5—C31108.80 (16)C21—C26—H26119.7
C11—C5—C31110.03 (17)C36—C31—C32117.2 (2)
C1—C5—C21111.18 (18)C36—C31—C5124.3 (2)
C11—C5—C21107.37 (17)C32—C31—C5118.42 (19)
C31—C5—C21110.53 (17)C33—C32—C31120.4 (2)
C12—C11—C15108.9 (2)C33—C32—H32119.8
C12—C11—C5127.6 (2)C31—C32—H32119.8
C15—C11—C5123.3 (2)C34—C33—C32121.0 (3)
C11—C12—C13110.7 (3)C34—C33—H33119.5
C11—C12—H12124.6C32—C33—H33119.5
C13—C12—H12124.6C35—C34—C33119.7 (3)
C12—C13—C14104.9 (2)C35—C34—H34120.2
C12—C13—H13A110.8C33—C34—H34120.2
C14—C13—H13A110.8C34—C35—C36120.4 (3)
C12—C13—H13B110.8C34—C35—H35119.8
C14—C13—H13B110.8C36—C35—H35119.8
H13A—C13—H13B108.8C35—C36—C31121.2 (2)
C15—C14—C13108.1 (2)C35—C36—H36119.4
C15—C14—H14125.9C31—C36—H36119.4
C13—C14—H14125.9
C3—N2—C1—N10.3 (3)C1—C5—C21—C2211.7 (3)
C3—N2—C1—C5−179.4 (2)C11—C5—C21—C22130.7 (2)
C2—N1—C1—N2−0.8 (3)C31—C5—C21—C22−109.2 (2)
C4—N1—C1—N2175.5 (3)C1—C5—C21—C26−168.7 (2)
C2—N1—C1—C5178.9 (2)C11—C5—C21—C26−49.7 (2)
C4—N1—C1—C5−4.8 (4)C31—C5—C21—C2670.3 (2)
C1—N1—C2—C30.9 (3)C26—C21—C22—C23−3.4 (4)
C4—N1—C2—C3−175.7 (3)C5—C21—C22—C23176.2 (2)
N1—C2—C3—N2−0.7 (3)C21—C22—C23—C240.2 (4)
C1—N2—C3—C20.2 (3)C22—C23—C24—C253.0 (5)
N2—C1—C5—C11−11.2 (3)C23—C24—C25—C26−3.0 (4)
N1—C1—C5—C11169.1 (2)C24—C25—C26—C21−0.3 (4)
N2—C1—C5—C31−131.2 (2)C22—C21—C26—C253.5 (3)
N1—C1—C5—C3149.2 (3)C5—C21—C26—C25−176.1 (2)
N2—C1—C5—C21106.9 (3)C1—C5—C31—C36−128.3 (2)
N1—C1—C5—C21−72.8 (2)C11—C5—C31—C36112.4 (2)
C1—C5—C11—C12−120.6 (3)C21—C5—C31—C36−6.0 (3)
C31—C5—C11—C12−1.5 (3)C1—C5—C31—C3249.8 (3)
C21—C5—C11—C12118.9 (3)C11—C5—C31—C32−69.5 (2)
C1—C5—C11—C1564.5 (3)C21—C5—C31—C32172.10 (19)
C31—C5—C11—C15−176.32 (19)C36—C31—C32—C330.9 (3)
C21—C5—C11—C15−56.0 (3)C5—C31—C32—C33−177.3 (2)
C15—C11—C12—C13−0.6 (3)C31—C32—C33—C34−1.0 (4)
C5—C11—C12—C13−176.1 (2)C32—C33—C34—C350.4 (5)
C11—C12—C13—C140.7 (3)C33—C34—C35—C360.3 (5)
C12—C13—C14—C15−0.5 (3)C34—C35—C36—C31−0.4 (4)
C13—C14—C15—C110.1 (3)C32—C31—C36—C35−0.2 (4)
C12—C11—C15—C140.3 (3)C5—C31—C36—C35177.9 (2)
C5—C11—C15—C14176.0 (2)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DN2523).

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