metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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(Di­ethyl ether){1-[2-(1-methyl-1H-imidazol-2-yl-κN3)-1,1-di­phenyl­ethyl]-(1,2,3,3a,7a-η)-inden­yl}lithium(I)

aThe North-West University of Xi'an, College of Chemistry and Material Science, Taibai Bei avenue 229, Xi'an 710069, Shaanxi Province, People's Republic of China
*Correspondence e-mail: maxborzov@mail.ru

(Received 22 March 2009; accepted 28 March 2009; online 2 April 2009)

In the title compound, [Li(C27H23N2)(C4H10O)], the Li atom possesses a nearly planar trigonal coordination environment (assuming the cyclo­penta­dienyl ring of the indenyl group occupies one coordination place). The diethyl ether ligand adopts a nearly planar W-type conformation.

Related literature

For the structural parameters of compounds with the (η5-1H-inden­yl)lithium fragment, see: Schumann et al. (2001[Schumann, H., Stenzel, O., Girgsdies, F. & Halterman, R. L. (2001). Organometallics, 20, 1743-1751.]); Cipot et al. (2003[Cipot, J., Wechsler, D., Stradiotto, M., McDonald, R. & Ferguson, M. J. (2003). Organometallics, 22, 5185-5192.]); Wang et al. (2005[Wang, H., Chan, H.-S., Okuda, J. & Xie, Z. (2005). Organometallics, 24, 3118-3124.]); Dinnebier et al. (1999[Dinnebier, R. E., Neander, S., Behrens, U. & Olbrich, F. (1999). Organometallics, 18, 2915-2918.]); Feng et al. (2005[Feng, Q.-Q., Li, Y.-M., Wang, S.-W., Zhou, S.-L., Sheng, E.-H. & Huang, Z.-X. (2005). Jiegou Huaxue, 24, 1046-1048.]); Faure et al. (2000[Faure, J.-L., Erker, G., Frohlich, R. & Bergander, K. (2000). Eur. J. Inorg. Chem. 2603-2606.]); Cheng et al. (2004[Cheng, J., Cui, D., Chen, W., Hu, N., Tang, T. & Huang, B. (2004). J. Organomet. Chem. 689, 2646-2653.]); Jones & Alan (2005[Jones, J. N. C. & Alan, H. (2005). Chem. Commun. pp. 1300-1302.]). For the (η5-9H-fluoren­yl)lithium counterpart of a similar structure, see: Culp & Cowley (1996[Culp, R. D. & Cowley, A. H. (1996). Organometallics, 15, 5380-5384.]). For the synthesis, see: Krut'ko et al. (2006[Krut'ko, D. P., Borzov, M. V., Liao, L., Nie, W., Churakov, A. V., Howard, J. A. K. & Lemenovskii, D. A. (2006). Russ. Chem. Bull. 55, 1574-1580.]).

[Scheme 1]

Experimental

Crystal data
  • [Li(C27H23N2)(C4H10O)]

  • Mr = 456.53

  • Orthorhombic, P b c a

  • a = 19.620 (2) Å

  • b = 12.8763 (13) Å

  • c = 20.698 (2) Å

  • V = 5229.0 (9) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 293 K

  • 0.32 × 0.21 × 0.11 mm

Data collection
  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.978, Tmax = 0.992

  • 24751 measured reflections

  • 4595 independent reflections

  • 2357 reflections with I > 2σ(I)

  • Rint = 0.056

Refinement
  • R[F2 > 2σ(F2)] = 0.048

  • wR(F2) = 0.152

  • S = 1.02

  • 4595 reflections

  • 320 parameters

  • 7 restraints

  • H-atom parameters constrained

  • Δρmax = 0.32 e Å−3

  • Δρmin = −0.20 e Å−3

Table 1
Selected geometric parameters (Å, °)

Li1—N2 2.004 (5)
Li1—O1 2.015 (4)
Li—Cp 2.041 (4)
N2—Li1—O1 105.98 (19)
C2—C3—N2 110.5 (2)

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Lithium indenides are important synthetic precursors of the related Group 4 transition metal complexes known as pre-catalysts for homogeneous a-olefin polymerization. Surprisingly, only few of them were structurally characterized (Schumann et al., 2001; Cipot et al., 2003; Wang et al., 2005; Dinnebier et al., 1999; Feng et al., 2005; Faure et al., 2000; Cheng et al., 2004; Jones & Alan, 2005).

In the molecule of I, the Li-atom possesses a nearly planar trigonal coordination environment [assuming the Cp-ring of the indenyl group occupying one coordination place; sum of the valent angles N2—Li1—O1 (105.98 (19)°), N2—Li1—Cpcent (122.3°) and O1—Li1—Cpcent (131.7°) equals 360.0°] (Fig. 1). The solvent molecule adopts a nearly planar W-conformation [methyl group atoms C42 and C44 deviate from the (C41, O1, C43) plane by 0.436 (6) and -0.045 (6) Å, respectively] and is involved, as a rigid group, into a rocking motion around O–Li bond (the max. principal thermal ellipsoid axes for the ether molecule atoms are nearly tangent in respect to rotation around O1–Li1 bond). Li1 – r. m. s. plane (C11 through C15) distance is 2.041 (4) Å (the same as Li1–Cpcent one). Coordination environment of O1 atom is essentially non-planar, with the angle between O1–Li1 bond and the normal to (C41, O1, C43) plane being equal to 54.1°.

Related literature top

For the structural parameters of compounds with the (η5-1H-indenyl)lithium fragment, see: Schumann et al. (2001); Cipot et al. (2003); Wang et al. (2005); Dinnebier et al. (1999); Feng et al. (2005); Faure et al. (2000); Cheng et al. (2004); Jones & Alan (2005). For the (η5-9H-fluorenyl)lithium counterpart of a similar structure, see: Culp et al. (1996). For the synthesis, see: Krut'ko et al. (2006).

Experimental top

All operations were performed in all-sealed glassware with application of the high-vacuum line technique (residual partial pressure of non-condensable gases below 1.5 × 10-3 torr), with traces of oxygen and moisture excluded. Solutions of (1-methyl-1H-imidazol-2-yl)methyllithium (adduct with THF 2: 1) [see (Krut'ko et al., 2006)] (2.234 g, 16.2 mmol) and 1-diphenylmethylidene-1H-indene (4.535 g, 16.2 mmol) in THF (total amount 100 ml) were mixed and heated at 60 °C for 1 h. The dark-blue solution was concentrated till dryness and the rest was extracted with diethyl ether that gave 7.42 g (86%) of the lithium salt Ia (adduct with TWO molecules of THF, 1H NMR spectral data) as dark-blue crystalline material. Single crystal of I (adduct with one molecule of THF) suitable for X-ray diffraction analysis was grown up from hot ether solution (slow cooling within 60 - 30 °C range, sealed vessel). Green crystals of I in THF-d8 form pink solution.

1H NMR (THF-d8, 22 °C) δ = 3.03 (s, 3 H, NCH3), 4.03 (s, 2 H, CH2), 5.95, 6.46 (both d, 1 H and 1 H, 3J = 3.4 Hz, CH=CH in indenide), 6.69 (both d, 1 H and 1 H, 3J = 1.2 Hz, CH=CH in imidazole), 6.24, 6.39, 6.79, 7.30 (all m, all 1 H, benz-CH in indene), 6.98–7.18 (m, 10 H, Ph-ring protons). 1H NMR (THF-d8, 22 °C) δ = 32.35 (NCH3), 37.30 (CH2), 55.98 (CPh2), 91.62, 108.97 (CH=CH in indene), 113.83, 114.02, 117.36, 120.31, 120.47, 120.64, 125.64, 126.25, 127.25 (double int.), 129.78, 130.56, 131.78 (unambiguous interpretement is not possible), 149.06 (C in Ph), 150.99 (N—C=N).

Refinement top

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. For Et2O atoms C41 through C44 and O1, the components of the anisotropic displacements along 1–2 and 1–3 directions were restrained to be the same with a standard uncertainty of 0.005 Å2.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of 1. Thermal ellpsoids are drawn at 30% probability level. All hydrogen atoms are omitted for clarity. Bonds from Li1 to N2, O1, and Cpcent are drawn as dashed lines.
(Diethyl ether){1-[2-(1-methyl-1H-imidazol-2-yl-κN3)-1,1- diphenylethyl]-(1,2,3,3a,7a-η)-indenyl}lithium(I) top
Crystal data top
[Li(C27H23N2)(C4H10O)]F(000) = 1952
Mr = 456.53Dx = 1.160 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 4629 reflections
a = 19.620 (2) Åθ = 2.2–21.0°
b = 12.8763 (13) ŵ = 0.07 mm1
c = 20.698 (2) ÅT = 293 K
V = 5229.0 (9) Å3Prism, green
Z = 80.32 × 0.21 × 0.11 mm
Data collection top
Bruker SMART APEX
diffractometer
4595 independent reflections
Radiation source: fine-focus sealed tube2357 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.056
ϕ and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2023
Tmin = 0.978, Tmax = 0.992k = 1515
24751 measured reflectionsl = 2424
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H-atom parameters constrained
wR(F2) = 0.152 w = 1/[σ2(Fo2) + (0.0739P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max < 0.001
4595 reflectionsΔρmax = 0.32 e Å3
320 parametersΔρmin = 0.20 e Å3
7 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0022 (5)
Crystal data top
[Li(C27H23N2)(C4H10O)]V = 5229.0 (9) Å3
Mr = 456.53Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 19.620 (2) ŵ = 0.07 mm1
b = 12.8763 (13) ÅT = 293 K
c = 20.698 (2) Å0.32 × 0.21 × 0.11 mm
Data collection top
Bruker SMART APEX
diffractometer
4595 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2357 reflections with I > 2σ(I)
Tmin = 0.978, Tmax = 0.992Rint = 0.056
24751 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0487 restraints
wR(F2) = 0.152H-atom parameters constrained
S = 1.02Δρmax = 0.32 e Å3
4595 reflectionsΔρmin = 0.20 e Å3
320 parameters
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*/Ueq
Li10.13031 (19)0.1533 (3)0.39839 (18)0.0771 (11)
N10.07860 (10)0.12724 (15)0.31605 (9)0.0698 (6)
N20.09933 (9)0.00828 (15)0.37892 (9)0.0687 (5)
C10.12154 (11)0.04750 (18)0.32932 (10)0.0599 (6)
C20.02674 (13)0.1227 (2)0.35940 (13)0.0855 (8)
H20.01110.16850.36220.103*
C30.03967 (13)0.0401 (2)0.39760 (13)0.0844 (8)
H30.01160.01830.43250.101*
C40.08482 (13)0.2031 (2)0.26429 (13)0.0920 (8)
H4A0.08310.16750.22250.138*
H4B0.04720.25300.26710.138*
H4C0.12830.23990.26840.138*
C50.18531 (10)0.02763 (18)0.29257 (10)0.0609 (6)
H5A0.19390.08750.26370.073*
H5B0.22370.02360.32350.073*
C60.18485 (9)0.07348 (17)0.25096 (9)0.0568 (6)
C110.17977 (10)0.16801 (17)0.29535 (9)0.0578 (6)
C120.13052 (12)0.24721 (19)0.29777 (11)0.0704 (6)
H120.09180.25130.27030.084*
C130.14622 (13)0.31901 (19)0.34603 (12)0.0781 (7)
H130.11990.37820.35730.094*
C140.20755 (13)0.2886 (2)0.37489 (11)0.0714 (7)
C150.22949 (11)0.19385 (19)0.34335 (10)0.0629 (6)
C160.29167 (12)0.1485 (2)0.36330 (10)0.0745 (7)
H160.30730.08640.34340.089*
C170.32949 (13)0.1942 (3)0.41150 (13)0.0918 (9)
H170.37140.16360.42430.110*
C180.30745 (17)0.2848 (3)0.44184 (12)0.0943 (9)
H180.33440.31430.47530.113*
C190.24817 (16)0.3318 (2)0.42462 (12)0.0883 (8)
H190.23400.39350.44590.106*
C210.12573 (10)0.06018 (17)0.20274 (10)0.0585 (6)
C220.05774 (11)0.06908 (17)0.22160 (11)0.0648 (6)
H220.04730.09150.26420.078*
C230.00511 (12)0.0457 (2)0.17914 (14)0.0782 (7)
H230.04080.05220.19320.094*
C240.01830 (14)0.0137 (2)0.11771 (14)0.0860 (8)
H240.01800.00080.08870.103*
C250.08479 (14)0.0028 (2)0.09833 (12)0.0858 (8)
H250.09460.02090.05590.103*
C260.13787 (12)0.02615 (19)0.14016 (10)0.0714 (7)
H260.18350.01870.12560.086*
C310.25269 (11)0.0834 (2)0.21395 (9)0.0674 (7)
C320.26254 (12)0.1724 (2)0.17666 (11)0.0826 (8)
H320.22800.22410.17510.099*
C330.32247 (17)0.1862 (3)0.14166 (13)0.1068 (11)
H330.32840.24600.11540.128*
C340.37300 (17)0.1127 (4)0.14541 (17)0.1193 (14)
H340.41430.12260.12220.143*
C350.36456 (14)0.0259 (3)0.18195 (15)0.1050 (11)
H350.40010.02410.18420.126*
C360.30438 (11)0.0097 (2)0.21600 (11)0.0798 (7)
H360.29860.05180.24070.096*
O10.10490 (8)0.17992 (15)0.49122 (8)0.0859 (5)
C410.06321 (18)0.2679 (2)0.50301 (14)0.1134 (10)
H41A0.08710.33190.48930.136*
H41B0.05300.27350.54970.136*
C420.00153 (17)0.2555 (3)0.46558 (18)0.1471 (15)
H42A0.00860.25700.41920.221*
H42C0.03270.31230.47630.221*
H42B0.02280.18900.47670.221*
C430.15656 (18)0.1729 (3)0.54066 (14)0.1278 (12)
H43B0.13500.16400.58350.153*
H43A0.18410.23730.54150.153*
C440.19980 (19)0.0846 (4)0.52646 (17)0.1513 (16)
H44A0.22890.10090.48930.227*
H44B0.17140.02420.51630.227*
H44C0.22830.06910.56410.227*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Li10.073 (3)0.080 (3)0.079 (2)0.002 (2)0.0148 (19)0.000 (2)
N10.0699 (13)0.0588 (14)0.0808 (13)0.0005 (11)0.0005 (10)0.0118 (11)
N20.0691 (12)0.0674 (13)0.0694 (11)0.0065 (11)0.0155 (10)0.0098 (10)
C10.0592 (14)0.0545 (15)0.0658 (13)0.0027 (12)0.0029 (11)0.0134 (11)
C20.0740 (18)0.080 (2)0.1020 (19)0.0060 (15)0.0127 (16)0.0216 (17)
C30.0792 (18)0.084 (2)0.0903 (18)0.0069 (15)0.0261 (14)0.0216 (16)
C40.105 (2)0.0691 (18)0.101 (2)0.0129 (15)0.0075 (16)0.0036 (16)
C50.0561 (13)0.0621 (15)0.0644 (13)0.0083 (11)0.0015 (10)0.0001 (11)
C60.0505 (12)0.0647 (15)0.0553 (11)0.0039 (10)0.0036 (10)0.0076 (10)
C110.0573 (13)0.0586 (15)0.0576 (12)0.0002 (11)0.0056 (10)0.0064 (11)
C120.0753 (16)0.0618 (16)0.0741 (15)0.0017 (13)0.0015 (12)0.0108 (13)
C130.096 (2)0.0555 (16)0.0830 (16)0.0026 (14)0.0119 (15)0.0007 (13)
C140.0816 (18)0.0638 (17)0.0689 (15)0.0199 (14)0.0126 (13)0.0063 (13)
C150.0610 (14)0.0717 (17)0.0559 (12)0.0118 (12)0.0086 (11)0.0047 (11)
C160.0617 (15)0.098 (2)0.0638 (13)0.0071 (13)0.0041 (12)0.0044 (13)
C170.0727 (17)0.131 (3)0.0716 (16)0.0215 (18)0.0024 (14)0.0006 (17)
C180.098 (2)0.113 (3)0.0716 (17)0.040 (2)0.0002 (16)0.0015 (18)
C190.108 (2)0.081 (2)0.0754 (17)0.0330 (18)0.0137 (16)0.0046 (14)
C210.0571 (14)0.0577 (15)0.0606 (13)0.0016 (10)0.0011 (10)0.0089 (11)
C220.0566 (14)0.0634 (16)0.0743 (14)0.0019 (11)0.0034 (12)0.0054 (12)
C230.0599 (15)0.0754 (19)0.0991 (19)0.0021 (13)0.0080 (14)0.0075 (15)
C240.0766 (19)0.089 (2)0.0928 (19)0.0124 (15)0.0246 (15)0.0046 (16)
C250.097 (2)0.092 (2)0.0691 (16)0.0149 (16)0.0119 (14)0.0037 (14)
C260.0684 (16)0.0810 (18)0.0648 (14)0.0056 (13)0.0023 (12)0.0010 (12)
C310.0559 (14)0.0929 (19)0.0535 (12)0.0075 (13)0.0004 (11)0.0026 (13)
C320.0733 (17)0.107 (2)0.0674 (14)0.0184 (15)0.0080 (12)0.0037 (15)
C330.102 (2)0.145 (3)0.0737 (17)0.044 (2)0.0214 (17)0.0050 (18)
C340.075 (2)0.185 (4)0.099 (2)0.038 (2)0.0293 (19)0.045 (3)
C350.0653 (19)0.158 (3)0.092 (2)0.0040 (19)0.0110 (16)0.038 (2)
C360.0557 (15)0.115 (2)0.0692 (15)0.0071 (15)0.0063 (12)0.0151 (14)
O10.0886 (12)0.0925 (14)0.0765 (11)0.0028 (10)0.0090 (9)0.0092 (9)
C410.157 (3)0.084 (2)0.100 (2)0.008 (2)0.0438 (19)0.0075 (17)
C420.115 (3)0.135 (3)0.191 (4)0.033 (2)0.034 (2)0.039 (3)
C430.129 (3)0.180 (4)0.0742 (18)0.011 (2)0.0022 (17)0.020 (2)
C440.125 (3)0.208 (4)0.121 (3)0.041 (3)0.012 (2)0.070 (3)
Geometric parameters (Å, º) top
Li1—N22.004 (5)C18—C191.359 (4)
Li1—O12.015 (4)C18—H180.9500
Li1—C152.315 (4)C19—H190.9500
Li1—C112.351 (4)C21—C261.388 (3)
Li1—C142.360 (5)C21—C221.395 (3)
Li1—C122.408 (5)C22—C231.389 (3)
Li1—C132.414 (5)C22—H220.9500
Li—Cp2.041 (4)C23—C241.361 (3)
N1—C11.356 (3)C23—H230.9500
N1—C21.358 (3)C24—C251.372 (3)
N1—C41.455 (3)C24—H240.9500
N2—C11.326 (3)C25—C261.387 (3)
N2—C31.381 (3)C25—H250.9500
C1—C51.486 (3)C26—H260.9500
C2—C31.349 (4)C31—C361.390 (3)
C2—H20.9500C31—C321.395 (3)
C3—H30.9500C32—C331.393 (3)
C4—H4A0.9800C32—H320.9500
C4—H4B0.9800C33—C341.373 (5)
C4—H4C0.9800C33—H330.9500
C5—C61.561 (3)C34—C351.359 (5)
C5—H5A0.9900C34—H340.9500
C5—H5B0.9900C35—C361.391 (4)
C6—C111.528 (3)C35—H350.9500
C6—C211.540 (3)C36—H360.9500
C6—C311.541 (3)O1—C411.419 (3)
C11—C121.406 (3)O1—C431.443 (3)
C11—C151.431 (3)C41—C421.496 (4)
C12—C131.396 (3)C41—H41A0.9900
C12—H120.9500C41—H41B0.9900
C13—C141.399 (3)C42—H42A0.9800
C13—H130.9500C42—H42C0.9800
C14—C191.416 (3)C42—H42B0.9800
C14—C151.449 (3)C43—C441.448 (5)
C15—C161.414 (3)C43—H43B0.9900
C16—C171.376 (3)C43—H43A0.9900
C16—H160.9500C44—H44A0.9800
C17—C181.393 (4)C44—H44B0.9800
C17—H170.9500C44—H44C0.9800
N2—Li1—O1105.98 (19)C11—C15—C14107.8 (2)
N2—Li1—C15111.48 (19)C16—C15—Li1119.22 (18)
O1—Li1—C15129.7 (2)C11—C15—Li173.52 (15)
N2—Li1—C1191.03 (16)C14—C15—Li173.66 (16)
O1—Li1—C11162.5 (2)C17—C16—C15120.0 (3)
C15—Li1—C1135.73 (9)C17—C16—H16120.0
N2—Li1—C14147.2 (2)C15—C16—H16120.0
O1—Li1—C14103.28 (19)C16—C17—C18121.2 (3)
C15—Li1—C1436.10 (10)C16—C17—H17119.4
C11—Li1—C1459.22 (12)C18—C17—H17119.4
N2—Li1—C12107.12 (19)C19—C18—C17121.4 (3)
O1—Li1—C12137.7 (2)C19—C18—H18119.3
C15—Li1—C1257.28 (12)C17—C18—H18119.3
C11—Li1—C1234.33 (9)C18—C19—C14119.8 (3)
C14—Li1—C1256.62 (12)C18—C19—H19120.1
N2—Li1—C13140.6 (2)C14—C19—H19120.1
O1—Li1—C13108.04 (19)C26—C21—C22116.83 (19)
C15—Li1—C1358.04 (13)C26—C21—C6120.71 (18)
C11—Li1—C1357.85 (12)C22—C21—C6122.00 (18)
C14—Li1—C1334.06 (10)C23—C22—C21121.1 (2)
C12—Li1—C1333.64 (10)C23—C22—H22119.5
C1—N1—C2107.4 (2)C21—C22—H22119.5
C1—N1—C4127.3 (2)C24—C23—C22121.0 (2)
C2—N1—C4125.3 (2)C24—C23—H23119.5
C1—N2—C3104.5 (2)C22—C23—H23119.5
C1—N2—Li1124.08 (18)C23—C24—C25119.0 (2)
C3—N2—Li1128.4 (2)C23—C24—H24120.5
N2—C1—N1111.26 (19)C25—C24—H24120.5
N2—C1—C5125.4 (2)C24—C25—C26120.6 (2)
N1—C1—C5123.3 (2)C24—C25—H25119.7
C3—C2—N1106.3 (2)C26—C25—H25119.7
C3—C2—H2126.8C25—C26—C21121.5 (2)
N1—C2—H2126.8C25—C26—H26119.3
C2—C3—N2110.5 (2)C21—C26—H26119.3
C2—C3—H3124.7C36—C31—C32118.5 (2)
N2—C3—H3124.7C36—C31—C6123.9 (2)
N1—C4—H4A109.5C32—C31—C6117.6 (2)
N1—C4—H4B109.5C33—C32—C31120.6 (3)
H4A—C4—H4B109.5C33—C32—H32119.7
N1—C4—H4C109.5C31—C32—H32119.7
H4A—C4—H4C109.5C34—C33—C32119.5 (3)
H4B—C4—H4C109.5C34—C33—H33120.3
C1—C5—C6114.90 (16)C32—C33—H33120.3
C1—C5—H5A108.5C35—C34—C33120.7 (3)
C6—C5—H5A108.5C35—C34—H34119.7
C1—C5—H5B108.5C33—C34—H34119.7
C6—C5—H5B108.5C34—C35—C36120.6 (3)
H5A—C5—H5B107.5C34—C35—H35119.7
C11—C6—C21115.41 (16)C36—C35—H35119.7
C11—C6—C31106.80 (17)C31—C36—C35120.1 (3)
C21—C6—C31109.73 (16)C31—C36—H36119.9
C11—C6—C5109.45 (16)C35—C36—H36119.9
C21—C6—C5105.62 (16)C41—O1—C43109.5 (3)
C31—C6—C5109.79 (17)C41—O1—Li1116.3 (2)
C12—C11—C15106.0 (2)C43—O1—Li1119.5 (2)
C12—C11—C6130.09 (19)O1—C41—C42108.4 (3)
C15—C11—C6123.91 (19)O1—C41—H41A110.0
C12—C11—Li175.08 (16)C42—C41—H41A110.0
C15—C11—Li170.76 (14)O1—C41—H41B110.0
C6—C11—Li1120.53 (17)C42—C41—H41B110.0
C13—C12—C11110.8 (2)H41A—C41—H41B108.4
C13—C12—Li173.38 (17)C41—C42—H42A109.5
C11—C12—Li170.59 (15)C41—C42—H42C109.5
C13—C12—H12124.6H42A—C42—H42C109.5
C11—C12—H12124.6C41—C42—H42B109.5
Li1—C12—H12123.0H42A—C42—H42B109.5
C12—C13—C14108.1 (2)H42C—C42—H42B109.5
C12—C13—Li172.97 (17)O1—C43—C44108.5 (3)
C14—C13—Li170.87 (16)O1—C43—H43B110.0
C12—C13—H13126.0C44—C43—H43B110.0
C14—C13—H13126.0O1—C43—H43A110.0
Li1—C13—H13121.9C44—C43—H43A110.0
C13—C14—C19133.2 (3)H43B—C43—H43A108.4
C13—C14—C15107.4 (2)C43—C44—H44A109.5
C19—C14—C15119.4 (3)C43—C44—H44B109.5
C13—C14—Li175.07 (17)H44A—C44—H44B109.5
C19—C14—Li1120.11 (18)C43—C44—H44C109.5
C15—C14—Li170.24 (15)H44A—C44—H44C109.5
C16—C15—C11134.0 (2)H44B—C44—H44C109.5
C16—C15—C14118.2 (2)
O1—Li1—N2—C1162.01 (19)C15—Li1—C14—C19113.3 (3)
C15—Li1—N2—C116.2 (3)C11—Li1—C14—C19151.4 (3)
C11—Li1—N2—C113.9 (3)C12—Li1—C14—C19168.0 (3)
C14—Li1—N2—C19.5 (5)C13—Li1—C14—C19131.6 (3)
C12—Li1—N2—C144.7 (3)N2—Li1—C14—C1510.6 (4)
C13—Li1—N2—C149.1 (4)O1—Li1—C14—C15142.3 (2)
O1—Li1—N2—C340.8 (3)C11—Li1—C14—C1538.10 (13)
C15—Li1—N2—C3173.4 (2)C12—Li1—C14—C1578.75 (15)
C11—Li1—N2—C3143.4 (2)C13—Li1—C14—C15115.1 (2)
C14—Li1—N2—C3166.7 (3)C12—C11—C15—C16177.6 (2)
C12—Li1—N2—C3112.6 (2)C6—C11—C15—C160.5 (4)
C13—Li1—N2—C3108.1 (3)Li1—C11—C15—C16115.0 (3)
C3—N2—C1—N10.5 (2)C12—C11—C15—C141.2 (2)
Li1—N2—C1—N1161.28 (19)C6—C11—C15—C14179.34 (17)
C3—N2—C1—C5179.0 (2)Li1—C11—C15—C1466.22 (17)
Li1—N2—C1—C519.3 (3)C12—C11—C15—Li167.45 (18)
C2—N1—C1—N20.4 (2)C6—C11—C15—Li1114.4 (2)
C4—N1—C1—N2178.2 (2)C13—C14—C15—C16178.70 (19)
C2—N1—C1—C5179.1 (2)C19—C14—C15—C160.7 (3)
C4—N1—C1—C52.3 (3)Li1—C14—C15—C16114.8 (2)
C1—N1—C2—C30.1 (3)C13—C14—C15—C110.3 (2)
C4—N1—C2—C3178.5 (2)C19—C14—C15—C11179.71 (18)
N1—C2—C3—N20.1 (3)Li1—C14—C15—C1166.12 (17)
C1—N2—C3—C20.4 (3)C13—C14—C15—Li166.46 (19)
Li1—N2—C3—C2160.3 (2)C19—C14—C15—Li1114.2 (2)
N2—C1—C5—C668.5 (3)N2—Li1—C15—C1672.6 (3)
N1—C1—C5—C6112.1 (2)O1—Li1—C15—C1662.8 (4)
C1—C5—C6—C1164.7 (2)C11—Li1—C15—C16131.6 (3)
C1—C5—C6—C2160.1 (2)C14—Li1—C15—C16113.6 (3)
C1—C5—C6—C31178.38 (18)C12—Li1—C15—C16169.6 (2)
C21—C6—C11—C122.4 (3)C13—Li1—C15—C16150.3 (2)
C31—C6—C11—C12119.9 (2)N2—Li1—C15—C1159.1 (2)
C5—C6—C11—C12121.3 (2)O1—Li1—C15—C11165.6 (3)
C21—C6—C11—C15179.99 (18)C14—Li1—C15—C11114.8 (2)
C31—C6—C11—C1557.7 (2)C12—Li1—C15—C1138.02 (13)
C5—C6—C11—C1561.1 (2)C13—Li1—C15—C1178.07 (15)
C21—C6—C11—Li193.7 (2)N2—Li1—C15—C14173.8 (2)
C31—C6—C11—Li1144.04 (18)O1—Li1—C15—C1450.8 (3)
C5—C6—C11—Li125.2 (2)C11—Li1—C15—C14114.8 (2)
N2—Li1—C11—C12119.73 (19)C12—Li1—C15—C1476.77 (16)
O1—Li1—C11—C1273.6 (8)C13—Li1—C15—C1436.72 (13)
C15—Li1—C11—C12113.2 (2)C11—C15—C16—C17178.8 (2)
C14—Li1—C11—C1274.73 (16)C14—C15—C16—C170.1 (3)
C13—Li1—C11—C1234.59 (14)Li1—C15—C16—C1786.1 (3)
N2—Li1—C11—C15127.0 (2)C15—C16—C17—C180.6 (4)
O1—Li1—C11—C1539.6 (7)C16—C17—C18—C190.6 (4)
C14—Li1—C11—C1538.51 (14)C17—C18—C19—C140.0 (4)
C12—Li1—C11—C15113.2 (2)C13—C14—C19—C18178.5 (2)
C13—Li1—C11—C1578.65 (15)C15—C14—C19—C180.6 (3)
N2—Li1—C11—C68.3 (2)Li1—C14—C19—C1883.6 (3)
O1—Li1—C11—C6158.3 (7)C11—C6—C21—C26141.1 (2)
C15—Li1—C11—C6118.7 (2)C31—C6—C21—C2620.4 (3)
C14—Li1—C11—C6157.20 (19)C5—C6—C21—C2697.8 (2)
C12—Li1—C11—C6128.1 (2)C11—C6—C21—C2246.9 (3)
C13—Li1—C11—C6162.66 (19)C31—C6—C21—C22167.6 (2)
C15—C11—C12—C131.7 (2)C5—C6—C21—C2274.1 (2)
C6—C11—C12—C13179.66 (19)C26—C21—C22—C230.6 (3)
Li1—C11—C12—C1362.8 (2)C6—C21—C22—C23172.9 (2)
C15—C11—C12—Li164.47 (17)C21—C22—C23—C240.2 (4)
C6—C11—C12—Li1117.6 (2)C22—C23—C24—C251.2 (4)
N2—Li1—C12—C13174.9 (2)C23—C24—C25—C261.4 (4)
O1—Li1—C12—C1334.8 (3)C24—C25—C26—C210.6 (4)
C15—Li1—C12—C1380.20 (17)C22—C21—C26—C250.4 (3)
C11—Li1—C12—C13119.8 (2)C6—C21—C26—C25172.8 (2)
C14—Li1—C12—C1336.81 (14)C11—C6—C31—C36121.2 (2)
N2—Li1—C12—C1165.30 (19)C21—C6—C31—C36113.0 (2)
O1—Li1—C12—C11154.6 (3)C5—C6—C31—C362.7 (3)
C15—Li1—C12—C1139.62 (13)C11—C6—C31—C3258.3 (2)
C14—Li1—C12—C1183.01 (16)C21—C6—C31—C3267.5 (2)
C13—Li1—C12—C11119.8 (2)C5—C6—C31—C32176.84 (19)
C11—C12—C13—C141.5 (3)C36—C31—C32—C330.8 (3)
Li1—C12—C13—C1462.59 (19)C6—C31—C32—C33179.6 (2)
C11—C12—C13—Li161.06 (18)C31—C32—C33—C341.8 (4)
N2—Li1—C13—C127.7 (3)C32—C33—C34—C351.2 (5)
O1—Li1—C13—C12156.2 (2)C33—C34—C35—C360.3 (5)
C15—Li1—C13—C1277.74 (16)C32—C31—C36—C350.7 (3)
C11—Li1—C13—C1235.30 (13)C6—C31—C36—C35178.8 (2)
C14—Li1—C13—C12116.7 (2)C34—C35—C36—C311.3 (4)
N2—Li1—C13—C14124.4 (3)N2—Li1—O1—C41124.0 (2)
O1—Li1—C13—C1487.1 (2)C15—Li1—O1—C4198.9 (3)
C15—Li1—C13—C1438.97 (14)C11—Li1—O1—C4169.9 (8)
C11—Li1—C13—C1481.41 (16)C14—Li1—O1—C4170.9 (3)
C12—Li1—C13—C14116.7 (2)C12—Li1—O1—C4116.4 (4)
C12—C13—C14—C19178.5 (2)C13—Li1—O1—C4135.8 (3)
Li1—C13—C14—C19117.5 (3)N2—Li1—O1—C43101.1 (3)
C12—C13—C14—C150.7 (2)C15—Li1—O1—C4336.0 (4)
Li1—C13—C14—C1563.25 (17)C11—Li1—O1—C4365.0 (8)
C12—C13—C14—Li163.95 (19)C14—Li1—O1—C4364.0 (3)
N2—Li1—C14—C13104.5 (4)C12—Li1—O1—C43118.5 (3)
O1—Li1—C14—C13102.6 (2)C13—Li1—O1—C4399.1 (3)
C15—Li1—C14—C13115.1 (2)C43—O1—C41—C42162.1 (3)
C11—Li1—C14—C1377.00 (16)Li1—O1—C41—C4258.7 (3)
C12—Li1—C14—C1336.35 (14)C41—O1—C43—C44178.1 (3)
N2—Li1—C14—C19123.9 (4)Li1—O1—C43—C4440.5 (4)
O1—Li1—C14—C1929.0 (3)

Experimental details

Crystal data
Chemical formula[Li(C27H23N2)(C4H10O)]
Mr456.53
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)293
a, b, c (Å)19.620 (2), 12.8763 (13), 20.698 (2)
V3)5229.0 (9)
Z8
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.32 × 0.21 × 0.11
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.978, 0.992
No. of measured, independent and
observed [I > 2σ(I)] reflections
24751, 4595, 2357
Rint0.056
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.152, 1.02
No. of reflections4595
No. of parameters320
No. of restraints7
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.32, 0.20

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top
Li1—N22.004 (5)Li—Cp2.041 (4)
Li1—O12.015 (4)
N2—Li1—O1105.98 (19)C2—C3—N2110.5 (2)
 

Footnotes

A part of the 2009 Master Degree thesis, North-West University of Xi'an.

Acknowledgements

Financial support from the National Natural Science Foundation of China (project No. B020205) is gratefully acknowledged. The authors are grateful to Mr Sun Wei for his help in measuring the NMR spectra. MVB is especially thankful to his former permanent co-author and old friend, Dr Andrei V. Churakov, for his invaluable advices in preparation of the material for this contribution.

References

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