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

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ISSN: 2056-9890

Bis[N,N′-bis­­[(1H-pyrrol-2-yl)methyl­ene]cyclo­hexane-1,2-di­amine]titanium(IV) tetra­hydro­furan solvate

aDepartment of Chemistry and Chemical Engineering, Suzhou University, Suzhou 215123, People's Republic of China, and bInstitute of Salt Lakes, Chinese Academy of Sciences, Xining City, Qinghai Province 810008, People's Republic of China
*Correspondence e-mail: liyahong@suda.edu.cn

(Received 21 December 2007; accepted 25 January 2008; online 30 January 2008)

In the title compound, [Ti(C16H18N4)2]·C4H8O, the TiIV ion is chelated by two Schiff base dianions with a TiN8 distorted square-anti­prismatic coordination geometry. The two cyclo­hexane rings assume the typical chair conformation. No hydrogen bonding is observed in the crystal structure.

Related literature

For general background, see: Li et al. (2002[Li, Y. H., Turnas, A., Ciszewski, J. T. & Odom, A. L. (2002). Inorg. Chem. 41, 6298-6306.]); Gardner et al. (2001[Gardner, J. D., Robson, D. A., Rees, L. H. & Mountford, P. (2001). Inorg. Chem. 40, 820-824.]); Han et al. (2007[Han, X. Y., Li, Y. H., Wei, H. & Zhang, Y. (2007). Chin. J. Chem. 25, 1334-1339.]).

[Scheme 1]

Experimental

Crystal data
  • [Ti(C16H18N4)2]·C4H8O

  • Mr = 652.69

  • Monoclinic, P 21 /c

  • a = 15.7746 (11) Å

  • b = 8.7372 (6) Å

  • c = 23.5824 (16) Å

  • β = 90.214 (1)°

  • V = 3250.2 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.31 mm−1

  • T = 293 (2) K

  • 0.44 × 0.34 × 0.24 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.877, Tmax = 0.931

  • 23461 measured reflections

  • 6052 independent reflections

  • 4955 reflections with I > 2σ(I)

  • Rint = 0.026

Refinement
  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 0.101

  • S = 1.03

  • 6052 reflections

  • 415 parameters

  • H-atom parameters constrained

  • Δρmax = 0.30 e Å−3

  • Δρmin = −0.29 e Å−3

Table 1
Selected bond lengths (Å)

Ti1—N1 2.1289 (16)
Ti1—N2 2.2283 (15)
Ti1—N3 2.2344 (16)
Ti1—N4 2.2706 (16)
Ti1—N5 2.2929 (16)
Ti1—N6 2.2234 (15)
Ti1—N7 2.2593 (16)
Ti1—N8 2.1647 (16)

Data collection: SMART (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

It is well known that titanium metal reacts with N-donor ligands to form lots of complexes (Li et al., 2002; Gardner et al., 2001). Complexes synthesized from titanium and pyrrol-2-yl Schiff base ligands are important in coordination chemistry and catalysis (Han et al., 2007). The bisligand coordinated titanium complexes are rare (Li et al., 2002). Herein we report the synthesis and crystal structure of the title titanium complex.

The compound is an mononuclear titanium(IV) complex (Fig. 1). The TiIV ion is coordinated by eight N atoms from two ligands, forming a distorted square-antiprism geometry (Table 1). The lattice THF molecule assumes an envelope conformation.

Related literature top

For general background, see: Li et al. (2002); Gardner et al. (2001); Han et al. (2007).

Experimental top

1. Synthesis of the ligand

To an ethanol solution (15 ml) of pyrrole-2-carbaldehyde (3.804 g, 4 mmol) was added a solution of cyclohexane-1,2-diamine (2.284 g, 2 mmol) in ethanol (10 ml). The resulting mixture was stirred at room temperature for 1 h, and then a few drops of acetic acid were added to yield a white muddle mixture. The solid was collected by filtration, washed with cold ethanol and dried under vacuum to get the crude products, finally was purified by recrystallization from ethanol.

2. Synthesis of the complex

To a solution of Ti(NMe2)4 (0.448 g, 2 mmol) in THF (5 ml) at -78 °C was added a solution of the above ligand (1.0734 g, 4 mmol) in THF dropwise. The resulting mixture was stirred overnight at room temperature to yield a black solution. The solvent was removed from reduced pressure and a black solid was obtained. The black solid was washed with hexane (3 × 15 ml) and black single crystals were obtained via recrystallization from THF/hexane mixture at room temperature after 3 weeks.

Refinement top

H atoms were placed in calculated positions with C—H = 0.93 (aromatic) or 0.97 Å (methylene) and refined in riding mode, Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. H atoms have been omitted for clarity.
Bis[N,N'-bis[(1H-pyrrol-2-yl)methylene]cyclohexane-1,2- diamine]titanium(IV) tetrahydrofuran solvate top
Crystal data top
[Ti(C16H18N4)2]·C4H8OF(000) = 1384
Mr = 652.69Dx = 1.334 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7300 reflections
a = 15.7746 (11) Åθ = 2.5–27.3°
b = 8.7372 (6) ŵ = 0.31 mm1
c = 23.5824 (16) ÅT = 293 K
β = 90.214 (1)°Block, black
V = 3250.2 (4) Å30.44 × 0.34 × 0.24 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
6052 independent reflections
Radiation source: fine-focus sealed tube4955 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.026
ϕ and ω scansθmax = 25.5°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1819
Tmin = 0.877, Tmax = 0.931k = 1010
23461 measured reflectionsl = 2828
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0465P)2 + 1.5415P]
where P = (Fo2 + 2Fc2)/3
6052 reflections(Δ/σ)max = 0.001
415 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.29 e Å3
Crystal data top
[Ti(C16H18N4)2]·C4H8OV = 3250.2 (4) Å3
Mr = 652.69Z = 4
Monoclinic, P21/cMo Kα radiation
a = 15.7746 (11) ŵ = 0.31 mm1
b = 8.7372 (6) ÅT = 293 K
c = 23.5824 (16) Å0.44 × 0.34 × 0.24 mm
β = 90.214 (1)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
6052 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
4955 reflections with I > 2σ(I)
Tmin = 0.877, Tmax = 0.931Rint = 0.026
23461 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.101H-atom parameters constrained
S = 1.03Δρmax = 0.31 e Å3
6052 reflectionsΔρmin = 0.29 e Å3
415 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
Ti10.22892 (2)0.45676 (4)0.457549 (14)0.02822 (10)
O10.30387 (15)0.7799 (3)0.23814 (11)0.0957 (7)
N10.29834 (10)0.66509 (18)0.45179 (7)0.0338 (4)
N20.33519 (10)0.43876 (18)0.51971 (7)0.0332 (4)
N30.20532 (10)0.26836 (18)0.51959 (7)0.0361 (4)
N40.16564 (10)0.25700 (18)0.41265 (7)0.0349 (4)
N50.18761 (10)0.58944 (18)0.53665 (7)0.0344 (4)
N60.09990 (9)0.55213 (17)0.44335 (7)0.0322 (3)
N70.20985 (10)0.52880 (18)0.36638 (7)0.0331 (4)
N80.33591 (10)0.37197 (18)0.40968 (7)0.0349 (4)
C10.28983 (14)0.8006 (2)0.42528 (10)0.0464 (5)
H10.24710.82400.39940.056*
C20.35369 (17)0.9008 (3)0.44180 (12)0.0625 (7)
H20.36081.00110.42940.075*
C30.40447 (15)0.8236 (3)0.47998 (11)0.0547 (6)
H30.45260.86110.49820.066*
C40.36938 (12)0.6782 (2)0.48590 (9)0.0380 (5)
C50.38696 (12)0.5526 (2)0.52143 (9)0.0388 (5)
H50.43410.55190.54520.047*
C60.34152 (13)0.3068 (2)0.55825 (8)0.0392 (5)
H60.36370.22080.53620.047*
C70.39832 (15)0.3249 (3)0.61032 (10)0.0537 (6)
H7A0.37970.41180.63260.064*
H7B0.45630.34320.59860.064*
C80.39389 (18)0.1792 (3)0.64598 (11)0.0706 (8)
H8A0.41990.09580.62520.085*
H8B0.42610.19410.68060.085*
C90.30358 (19)0.1351 (3)0.66102 (11)0.0694 (8)
H9A0.27970.21240.68580.083*
H9B0.30410.03870.68150.083*
C100.24785 (17)0.1193 (3)0.60826 (10)0.0559 (6)
H10A0.26800.03500.58510.067*
H10B0.18990.09740.61940.067*
C110.25059 (13)0.2674 (2)0.57418 (8)0.0392 (5)
H110.22810.35030.59780.047*
C120.16251 (13)0.1497 (2)0.50368 (9)0.0403 (5)
H120.14900.07250.52920.048*
C130.13727 (12)0.1411 (2)0.44710 (9)0.0365 (4)
C140.10000 (14)0.0242 (2)0.41541 (10)0.0460 (5)
H140.07600.06560.42920.055*
C150.10594 (14)0.0686 (2)0.35952 (10)0.0455 (5)
H150.08670.01450.32800.055*
C160.14637 (13)0.2102 (2)0.35930 (9)0.0413 (5)
H160.15860.26570.32670.050*
C170.21998 (13)0.6389 (2)0.58649 (9)0.0415 (5)
H170.27370.61360.59990.050*
C180.16340 (14)0.7320 (2)0.61535 (9)0.0449 (5)
H180.17210.77810.65040.054*
C190.09170 (14)0.7427 (2)0.58181 (9)0.0434 (5)
H190.04260.79760.58960.052*
C200.10798 (12)0.6543 (2)0.53367 (8)0.0343 (4)
C210.06392 (12)0.6318 (2)0.48316 (8)0.0354 (4)
H210.01000.67280.47800.043*
C220.06192 (12)0.5472 (2)0.38635 (8)0.0343 (4)
H220.05160.43960.37680.041*
C230.02049 (13)0.6350 (2)0.37604 (9)0.0437 (5)
H23A0.01260.74220.38540.052*
H23B0.06500.59430.40000.052*
C240.04587 (14)0.6190 (3)0.31342 (10)0.0534 (6)
H24A0.05830.51250.30530.064*
H24B0.09700.67790.30640.064*
C250.02408 (15)0.6744 (3)0.27410 (10)0.0558 (6)
H25A0.03290.78320.27980.067*
H25B0.00670.65890.23500.067*
C260.10726 (14)0.5891 (3)0.28511 (9)0.0480 (5)
H26A0.10050.48170.27580.058*
H26B0.15170.63100.26140.058*
C270.13184 (12)0.6060 (2)0.34756 (8)0.0359 (4)
H270.13880.71550.35520.043*
C280.27018 (13)0.4974 (2)0.33193 (9)0.0406 (5)
H280.26780.52810.29420.049*
C290.34005 (13)0.4148 (2)0.35323 (9)0.0406 (5)
C300.41538 (14)0.3658 (3)0.32947 (10)0.0524 (6)
H300.43290.38080.29230.063*
C310.45961 (14)0.2901 (3)0.37197 (10)0.0508 (6)
H310.51250.24390.36880.061*
C320.40960 (12)0.2968 (2)0.42010 (9)0.0409 (5)
H320.42460.25510.45500.049*
C330.3873 (2)0.7946 (4)0.2598 (2)0.1107 (14)
H33A0.42790.76140.23150.133*
H33B0.39410.73090.29320.133*
C340.4027 (2)0.9553 (4)0.27450 (18)0.0978 (11)
H34A0.43491.00620.24500.117*
H34B0.43360.96330.31000.117*
C350.31730 (19)1.0227 (4)0.27958 (14)0.0783 (8)
H35A0.30131.03240.31910.094*
H35B0.31531.12310.26200.094*
C360.2606 (2)0.9156 (4)0.24985 (16)0.0888 (10)
H36A0.21170.89390.27330.107*
H36B0.24090.96140.21470.107*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ti10.02674 (18)0.02732 (18)0.03059 (18)0.00220 (13)0.00331 (13)0.00056 (13)
O10.0962 (17)0.0741 (15)0.1167 (19)0.0006 (13)0.0101 (14)0.0173 (13)
N10.0332 (8)0.0305 (8)0.0376 (9)0.0039 (7)0.0047 (7)0.0007 (7)
N20.0300 (8)0.0331 (8)0.0365 (9)0.0014 (7)0.0041 (7)0.0004 (7)
N30.0382 (9)0.0333 (9)0.0367 (9)0.0034 (7)0.0034 (7)0.0021 (7)
N40.0351 (9)0.0300 (8)0.0396 (9)0.0008 (7)0.0052 (7)0.0021 (7)
N50.0345 (9)0.0325 (8)0.0362 (9)0.0014 (7)0.0009 (7)0.0013 (7)
N60.0292 (8)0.0307 (8)0.0366 (9)0.0022 (7)0.0031 (7)0.0023 (7)
N70.0318 (8)0.0339 (9)0.0337 (8)0.0059 (7)0.0034 (7)0.0014 (7)
N80.0305 (8)0.0341 (9)0.0401 (9)0.0026 (7)0.0017 (7)0.0028 (7)
C10.0491 (13)0.0360 (11)0.0541 (13)0.0057 (10)0.0117 (10)0.0059 (10)
C20.0733 (17)0.0354 (12)0.0786 (18)0.0194 (12)0.0214 (14)0.0123 (12)
C30.0509 (14)0.0441 (13)0.0689 (16)0.0183 (11)0.0164 (12)0.0018 (11)
C40.0340 (10)0.0366 (11)0.0434 (11)0.0068 (8)0.0059 (9)0.0011 (9)
C50.0298 (10)0.0434 (12)0.0432 (11)0.0019 (9)0.0102 (8)0.0033 (9)
C60.0417 (11)0.0375 (11)0.0383 (11)0.0063 (9)0.0074 (9)0.0036 (9)
C70.0509 (14)0.0614 (15)0.0487 (13)0.0039 (11)0.0171 (11)0.0074 (11)
C80.082 (2)0.0743 (18)0.0558 (16)0.0111 (15)0.0279 (14)0.0159 (14)
C90.095 (2)0.0637 (17)0.0495 (15)0.0052 (15)0.0161 (14)0.0214 (13)
C100.0734 (16)0.0468 (13)0.0472 (13)0.0067 (12)0.0074 (12)0.0125 (11)
C110.0488 (12)0.0352 (11)0.0335 (10)0.0010 (9)0.0061 (9)0.0030 (8)
C120.0412 (11)0.0330 (10)0.0467 (12)0.0059 (9)0.0004 (9)0.0063 (9)
C130.0331 (10)0.0291 (10)0.0472 (12)0.0025 (8)0.0052 (8)0.0024 (9)
C140.0437 (12)0.0303 (11)0.0638 (15)0.0054 (9)0.0097 (10)0.0020 (10)
C150.0465 (12)0.0346 (11)0.0553 (14)0.0034 (9)0.0153 (10)0.0132 (10)
C160.0466 (12)0.0368 (11)0.0404 (11)0.0019 (9)0.0059 (9)0.0039 (9)
C170.0437 (12)0.0406 (11)0.0400 (11)0.0011 (9)0.0071 (9)0.0027 (9)
C180.0600 (14)0.0370 (11)0.0375 (11)0.0005 (10)0.0002 (10)0.0064 (9)
C190.0477 (12)0.0379 (11)0.0445 (12)0.0075 (9)0.0075 (10)0.0004 (9)
C200.0348 (10)0.0312 (10)0.0370 (11)0.0014 (8)0.0034 (8)0.0029 (8)
C210.0295 (10)0.0315 (10)0.0453 (11)0.0010 (8)0.0014 (8)0.0060 (9)
C220.0323 (10)0.0319 (10)0.0386 (10)0.0034 (8)0.0087 (8)0.0021 (8)
C230.0357 (11)0.0390 (11)0.0562 (13)0.0004 (9)0.0115 (9)0.0027 (10)
C240.0452 (13)0.0529 (14)0.0620 (15)0.0017 (11)0.0251 (11)0.0014 (12)
C250.0612 (15)0.0568 (14)0.0494 (14)0.0063 (12)0.0279 (12)0.0075 (11)
C260.0507 (13)0.0542 (13)0.0391 (12)0.0089 (11)0.0119 (10)0.0047 (10)
C270.0352 (10)0.0351 (10)0.0375 (11)0.0047 (8)0.0104 (8)0.0035 (8)
C280.0415 (11)0.0491 (12)0.0312 (10)0.0082 (9)0.0009 (9)0.0017 (9)
C290.0365 (11)0.0474 (12)0.0378 (11)0.0039 (9)0.0029 (8)0.0028 (9)
C300.0428 (12)0.0679 (16)0.0465 (13)0.0025 (11)0.0108 (10)0.0069 (12)
C310.0330 (11)0.0575 (14)0.0621 (15)0.0040 (10)0.0040 (10)0.0146 (12)
C320.0337 (11)0.0385 (11)0.0507 (12)0.0005 (9)0.0040 (9)0.0052 (9)
C330.062 (2)0.074 (2)0.197 (4)0.0054 (17)0.030 (2)0.012 (3)
C340.066 (2)0.096 (3)0.132 (3)0.0034 (18)0.001 (2)0.024 (2)
C350.076 (2)0.073 (2)0.086 (2)0.0042 (16)0.0047 (16)0.0032 (16)
C360.070 (2)0.087 (2)0.110 (3)0.0045 (17)0.0120 (18)0.020 (2)
Geometric parameters (Å, º) top
Ti1—N12.1289 (16)C12—H120.9300
Ti1—N22.2283 (15)C13—C141.394 (3)
Ti1—N32.2344 (16)C14—C151.378 (3)
Ti1—N42.2706 (16)C14—H140.9300
Ti1—N52.2929 (16)C15—C161.392 (3)
Ti1—N62.2234 (15)C15—H150.9300
Ti1—N72.2593 (16)C16—H160.9300
Ti1—N82.1647 (16)C17—C181.388 (3)
O1—C361.396 (4)C17—H170.9300
O1—C331.415 (4)C18—C191.381 (3)
N1—C11.345 (3)C18—H180.9300
N1—C41.382 (2)C19—C201.398 (3)
N2—C51.288 (2)C19—H190.9300
N2—C61.471 (2)C20—C211.391 (3)
N3—C121.292 (2)C21—H210.9300
N3—C111.470 (2)C22—C271.525 (3)
N4—C161.356 (3)C22—C231.528 (3)
N4—C131.374 (2)C22—H220.9800
N5—C171.351 (3)C23—C241.535 (3)
N5—C201.380 (2)C23—H23A0.9700
N6—C211.301 (2)C23—H23B0.9700
N6—C221.470 (2)C24—C251.523 (3)
N7—C281.283 (3)C24—H24A0.9700
N7—C271.470 (2)C24—H24B0.9700
N8—C321.357 (2)C25—C261.530 (3)
N8—C291.385 (3)C25—H25A0.9700
C1—C21.390 (3)C25—H25B0.9700
C1—H10.9300C26—C271.529 (3)
C2—C31.379 (3)C26—H26A0.9700
C2—H20.9300C26—H26B0.9700
C3—C41.393 (3)C27—H270.9800
C3—H30.9300C28—C291.408 (3)
C4—C51.407 (3)C28—H280.9300
C5—H50.9300C29—C301.384 (3)
C6—C111.523 (3)C30—C311.387 (3)
C6—C71.525 (3)C30—H300.9300
C6—H60.9800C31—C321.386 (3)
C7—C81.528 (4)C31—H310.9300
C7—H7A0.9700C32—H320.9300
C7—H7B0.9700C33—C341.466 (5)
C8—C91.519 (4)C33—H33A0.9700
C8—H8A0.9700C33—H33B0.9700
C8—H8B0.9700C34—C351.476 (4)
C9—C101.527 (3)C34—H34A0.9700
C9—H9A0.9700C34—H34B0.9700
C9—H9B0.9700C35—C361.470 (4)
C10—C111.525 (3)C35—H35A0.9700
C10—H10A0.9700C35—H35B0.9700
C10—H10B0.9700C36—H36A0.9700
C11—H110.9800C36—H36B0.9700
C12—C131.393 (3)
N1—Ti1—N881.79 (6)N3—C12—H12121.0
N1—Ti1—N698.09 (6)C13—C12—H12121.0
N8—Ti1—N6139.89 (6)N4—C13—C12115.70 (17)
N1—Ti1—N273.52 (6)N4—C13—C14111.15 (18)
N8—Ti1—N274.50 (6)C12—C13—C14132.18 (19)
N6—Ti1—N2144.24 (6)C15—C14—C13106.04 (19)
N1—Ti1—N3139.35 (6)C15—C14—H14127.0
N8—Ti1—N3102.79 (6)C13—C14—H14127.0
N6—Ti1—N3102.71 (6)C14—C15—C16106.66 (19)
N2—Ti1—N369.15 (6)C14—C15—H15126.7
N1—Ti1—N776.57 (6)C16—C15—H15126.7
N8—Ti1—N772.56 (6)N4—C16—C15111.45 (19)
N6—Ti1—N768.51 (6)N4—C16—H16124.3
N2—Ti1—N7137.97 (6)C15—C16—H16124.3
N3—Ti1—N7143.75 (6)N5—C17—C18111.87 (18)
N1—Ti1—N4148.52 (6)N5—C17—H17124.1
N8—Ti1—N480.56 (6)C18—C17—H17124.1
N6—Ti1—N479.47 (6)C19—C18—C17106.61 (19)
N2—Ti1—N4125.51 (6)C19—C18—H18126.7
N3—Ti1—N470.43 (6)C17—C18—H18126.7
N7—Ti1—N473.36 (6)C18—C19—C20105.96 (18)
N1—Ti1—N576.55 (6)C18—C19—H19127.0
N8—Ti1—N5145.27 (6)C20—C19—H19127.0
N6—Ti1—N570.75 (6)N5—C20—C21115.96 (17)
N2—Ti1—N573.49 (6)N5—C20—C19110.83 (17)
N3—Ti1—N577.95 (6)C21—C20—C19132.91 (19)
N7—Ti1—N5126.59 (6)N6—C21—C20118.40 (17)
N4—Ti1—N5129.96 (6)N6—C21—H21120.8
C36—O1—C33107.8 (3)C20—C21—H21120.8
C1—N1—C4106.07 (16)N6—C22—C27104.20 (14)
C1—N1—Ti1137.02 (14)N6—C22—C23118.31 (17)
C4—N1—Ti1116.75 (12)C27—C22—C23110.62 (16)
C5—N2—C6122.99 (16)N6—C22—H22107.8
C5—N2—Ti1116.20 (13)C27—C22—H22107.8
C6—N2—Ti1120.72 (12)C23—C22—H22107.8
C12—N3—C11120.11 (17)C22—C23—C24109.02 (18)
C12—N3—Ti1119.28 (13)C22—C23—H23A109.9
C11—N3—Ti1119.73 (12)C24—C23—H23A109.9
C16—N4—C13104.70 (16)C22—C23—H23B109.9
C16—N4—Ti1139.54 (14)C24—C23—H23B109.9
C13—N4—Ti1115.75 (12)H23A—C23—H23B108.3
C17—N5—C20104.73 (16)C25—C24—C23111.70 (18)
C17—N5—Ti1139.64 (13)C25—C24—H24A109.3
C20—N5—Ti1115.32 (12)C23—C24—H24A109.3
C21—N6—C22119.87 (16)C25—C24—H24B109.3
C21—N6—Ti1119.57 (13)C23—C24—H24B109.3
C22—N6—Ti1119.76 (12)H24A—C24—H24B107.9
C28—N7—C27121.93 (17)C24—C25—C26111.37 (19)
C28—N7—Ti1116.52 (13)C24—C25—H25A109.4
C27—N7—Ti1121.55 (12)C26—C25—H25A109.4
C32—N8—C29105.17 (16)C24—C25—H25B109.4
C32—N8—Ti1137.76 (14)C26—C25—H25B109.4
C29—N8—Ti1116.64 (13)H25A—C25—H25B108.0
N1—C1—C2110.69 (19)C27—C26—C25109.32 (19)
N1—C1—H1124.7C27—C26—H26A109.8
C2—C1—H1124.7C25—C26—H26A109.8
C3—C2—C1107.1 (2)C27—C26—H26B109.8
C3—C2—H2126.5C25—C26—H26B109.8
C1—C2—H2126.5H26A—C26—H26B108.3
C2—C3—C4106.35 (19)N7—C27—C22105.71 (15)
C2—C3—H3126.8N7—C27—C26117.10 (17)
C4—C3—H3126.8C22—C27—C26111.35 (16)
N1—C4—C3109.82 (18)N7—C27—H27107.4
N1—C4—C5116.07 (17)C22—C27—H27107.4
C3—C4—C5133.88 (19)C26—C27—H27107.4
N2—C5—C4117.40 (17)N7—C28—C29117.71 (19)
N2—C5—H5121.3N7—C28—H28121.1
C4—C5—H5121.3C29—C28—H28121.1
N2—C6—C11105.52 (15)C30—C29—N8110.45 (19)
N2—C6—C7117.03 (17)C30—C29—C28133.3 (2)
C11—C6—C7112.07 (18)N8—C29—C28116.22 (18)
N2—C6—H6107.3C29—C30—C31106.6 (2)
C11—C6—H6107.3C29—C30—H30126.7
C7—C6—H6107.3C31—C30—H30126.7
C6—C7—C8109.2 (2)C32—C31—C30106.59 (19)
C6—C7—H7A109.8C32—C31—H31126.7
C8—C7—H7A109.8C30—C31—H31126.7
C6—C7—H7B109.8N8—C32—C31111.2 (2)
C8—C7—H7B109.8N8—C32—H32124.4
H7A—C7—H7B108.3C31—C32—H32124.4
C9—C8—C7112.6 (2)O1—C33—C34109.0 (3)
C9—C8—H8A109.1O1—C33—H33A109.9
C7—C8—H8A109.1C34—C33—H33A109.9
C9—C8—H8B109.1O1—C33—H33B109.9
C7—C8—H8B109.1C34—C33—H33B109.9
H8A—C8—H8B107.8H33A—C33—H33B108.3
C8—C9—C10111.7 (2)C33—C34—C35104.5 (3)
C8—C9—H9A109.3C33—C34—H34A110.9
C10—C9—H9A109.3C35—C34—H34A110.9
C8—C9—H9B109.3C33—C34—H34B110.9
C10—C9—H9B109.3C35—C34—H34B110.9
H9A—C9—H9B107.9H34A—C34—H34B108.9
C11—C10—C9109.6 (2)C36—C35—C34105.1 (3)
C11—C10—H10A109.8C36—C35—H35A110.7
C9—C10—H10A109.8C34—C35—H35A110.7
C11—C10—H10B109.8C36—C35—H35B110.7
C9—C10—H10B109.8C34—C35—H35B110.7
H10A—C10—H10B108.2H35A—C35—H35B108.8
N3—C11—C6103.74 (15)O1—C36—C35109.8 (3)
N3—C11—C10116.86 (17)O1—C36—H36A109.7
C6—C11—C10110.52 (18)C35—C36—H36A109.7
N3—C11—H11108.5O1—C36—H36B109.7
C6—C11—H11108.5C35—C36—H36B109.7
C10—C11—H11108.5H36A—C36—H36B108.2
N3—C12—C13117.96 (18)
N8—Ti1—N1—C1110.8 (2)N6—Ti1—N8—C2919.56 (18)
N6—Ti1—N1—C128.6 (2)N2—Ti1—N8—C29148.36 (15)
N2—Ti1—N1—C1173.0 (2)N3—Ti1—N8—C29147.86 (14)
N3—Ti1—N1—C1149.07 (19)N7—Ti1—N8—C295.16 (13)
N7—Ti1—N1—C136.9 (2)N4—Ti1—N8—C2980.56 (14)
N4—Ti1—N1—C154.4 (3)N5—Ti1—N8—C29124.91 (14)
N5—Ti1—N1—C196.5 (2)C4—N1—C1—C20.3 (3)
N8—Ti1—N1—C474.52 (14)Ti1—N1—C1—C2174.77 (18)
N6—Ti1—N1—C4146.02 (14)N1—C1—C2—C30.4 (3)
N2—Ti1—N1—C41.66 (14)C1—C2—C3—C40.4 (3)
N3—Ti1—N1—C425.58 (19)C1—N1—C4—C30.0 (2)
N7—Ti1—N1—C4148.45 (15)Ti1—N1—C4—C3176.24 (15)
N4—Ti1—N1—C4130.94 (14)C1—N1—C4—C5175.17 (19)
N5—Ti1—N1—C478.13 (14)Ti1—N1—C4—C51.0 (2)
N1—Ti1—N2—C52.26 (14)C2—C3—C4—N10.3 (3)
N8—Ti1—N2—C583.58 (15)C2—C3—C4—C5173.7 (3)
N6—Ti1—N2—C583.07 (17)C6—N2—C5—C4174.16 (18)
N3—Ti1—N2—C5165.84 (16)Ti1—N2—C5—C42.5 (2)
N7—Ti1—N2—C544.13 (18)N1—C4—C5—N21.0 (3)
N4—Ti1—N2—C5149.57 (14)C3—C4—C5—N2172.7 (2)
N5—Ti1—N2—C582.74 (15)C5—N2—C6—C11139.94 (19)
N1—Ti1—N2—C6174.48 (15)Ti1—N2—C6—C1136.56 (19)
N8—Ti1—N2—C699.69 (14)C5—N2—C6—C714.5 (3)
N6—Ti1—N2—C693.66 (16)Ti1—N2—C6—C7161.97 (15)
N3—Ti1—N2—C610.89 (13)N2—C6—C7—C8177.8 (2)
N7—Ti1—N2—C6139.14 (13)C11—C6—C7—C855.7 (3)
N4—Ti1—N2—C633.70 (16)C6—C7—C8—C953.9 (3)
N5—Ti1—N2—C693.99 (14)C7—C8—C9—C1055.3 (3)
N1—Ti1—N3—C12173.70 (14)C8—C9—C10—C1155.9 (3)
N8—Ti1—N3—C1281.44 (16)C12—N3—C11—C6125.00 (19)
N6—Ti1—N3—C1267.34 (16)Ti1—N3—C11—C644.17 (19)
N2—Ti1—N3—C12149.12 (17)C12—N3—C11—C103.1 (3)
N7—Ti1—N3—C123.6 (2)Ti1—N3—C11—C10166.06 (16)
N4—Ti1—N3—C126.46 (15)N2—C6—C11—N346.80 (19)
N5—Ti1—N3—C12134.15 (16)C7—C6—C11—N3175.23 (17)
N1—Ti1—N3—C114.44 (19)N2—C6—C11—C10172.82 (17)
N8—Ti1—N3—C1187.83 (15)C7—C6—C11—C1058.7 (2)
N6—Ti1—N3—C11123.40 (14)C9—C10—C11—N3175.6 (2)
N2—Ti1—N3—C1120.14 (14)C9—C10—C11—C657.3 (3)
N7—Ti1—N3—C11165.71 (13)C11—N3—C12—C13165.45 (18)
N4—Ti1—N3—C11162.80 (15)Ti1—N3—C12—C133.8 (2)
N5—Ti1—N3—C1156.59 (14)C16—N4—C13—C12169.51 (18)
N1—Ti1—N4—C166.4 (3)Ti1—N4—C13—C129.6 (2)
N8—Ti1—N4—C1663.1 (2)C16—N4—C13—C140.6 (2)
N6—Ti1—N4—C1681.9 (2)Ti1—N4—C13—C14179.69 (13)
N2—Ti1—N4—C16126.3 (2)N3—C12—C13—N44.0 (3)
N3—Ti1—N4—C16170.4 (2)N3—C12—C13—C14171.5 (2)
N7—Ti1—N4—C1611.4 (2)N4—C13—C14—C150.4 (2)
N5—Ti1—N4—C16135.55 (19)C12—C13—C14—C15167.5 (2)
N1—Ti1—N4—C13172.28 (13)C13—C14—C15—C160.0 (2)
N8—Ti1—N4—C13115.57 (14)C13—N4—C16—C150.6 (2)
N6—Ti1—N4—C1399.41 (14)Ti1—N4—C16—C15179.32 (15)
N2—Ti1—N4—C1352.40 (15)C14—C15—C16—N40.3 (2)
N3—Ti1—N4—C138.27 (13)C20—N5—C17—C180.4 (2)
N7—Ti1—N4—C13169.94 (14)Ti1—N5—C17—C18173.18 (15)
N5—Ti1—N4—C1345.79 (16)N5—C17—C18—C190.4 (3)
N1—Ti1—N5—C1768.2 (2)C17—C18—C19—C200.2 (2)
N8—Ti1—N5—C1715.3 (3)C17—N5—C20—C21174.29 (17)
N6—Ti1—N5—C17171.9 (2)Ti1—N5—C20—C210.6 (2)
N2—Ti1—N5—C178.3 (2)C17—N5—C20—C190.2 (2)
N3—Ti1—N5—C1779.8 (2)Ti1—N5—C20—C19175.08 (13)
N7—Ti1—N5—C17129.9 (2)C18—C19—C20—N50.0 (2)
N4—Ti1—N5—C17131.1 (2)C18—C19—C20—C21173.3 (2)
N1—Ti1—N5—C20104.06 (14)C22—N6—C21—C20169.89 (16)
N8—Ti1—N5—C20157.00 (12)Ti1—N6—C21—C200.1 (2)
N6—Ti1—N5—C200.37 (12)N5—C20—C21—N60.5 (3)
N2—Ti1—N5—C20179.43 (14)C19—C20—C21—N6173.5 (2)
N3—Ti1—N5—C20107.87 (14)C21—N6—C22—C27122.29 (18)
N7—Ti1—N5—C2042.42 (15)Ti1—N6—C22—C2747.47 (17)
N4—Ti1—N5—C2056.60 (15)C21—N6—C22—C231.0 (3)
N1—Ti1—N6—C2172.77 (14)Ti1—N6—C22—C23170.76 (13)
N8—Ti1—N6—C21159.60 (13)N6—C22—C23—C24177.60 (17)
N2—Ti1—N6—C210.20 (19)C27—C22—C23—C2457.6 (2)
N3—Ti1—N6—C2172.08 (14)C22—C23—C24—C2556.7 (2)
N7—Ti1—N6—C21144.83 (15)C23—C24—C25—C2656.8 (3)
N4—Ti1—N6—C21139.05 (15)C24—C25—C26—C2755.7 (2)
N5—Ti1—N6—C210.14 (13)C28—N7—C27—C22149.55 (18)
N1—Ti1—N6—C2297.01 (13)Ti1—N7—C27—C2229.71 (19)
N8—Ti1—N6—C2210.18 (17)C28—N7—C27—C2624.9 (3)
N2—Ti1—N6—C22169.99 (12)Ti1—N7—C27—C26154.37 (14)
N3—Ti1—N6—C22118.14 (13)N6—C22—C27—N744.41 (18)
N7—Ti1—N6—C2224.95 (12)C23—C22—C27—N7172.57 (16)
N4—Ti1—N6—C2251.17 (13)N6—C22—C27—C26172.58 (16)
N5—Ti1—N6—C22169.65 (14)C23—C22—C27—C2659.3 (2)
N1—Ti1—N7—C2880.97 (15)C25—C26—C27—N7178.97 (17)
N8—Ti1—N7—C284.50 (14)C25—C26—C27—C2257.2 (2)
N6—Ti1—N7—C28174.59 (16)C27—N7—C28—C29176.14 (18)
N2—Ti1—N7—C2835.43 (18)Ti1—N7—C28—C293.2 (2)
N3—Ti1—N7—C2892.45 (16)C32—N8—C29—C300.2 (2)
N4—Ti1—N7—C2889.60 (15)Ti1—N8—C29—C30174.01 (15)
N5—Ti1—N7—C28142.60 (14)C32—N8—C29—C28179.39 (18)
N1—Ti1—N7—C2799.73 (14)Ti1—N8—C29—C285.6 (2)
N8—Ti1—N7—C27174.80 (14)N7—C28—C29—C30178.0 (2)
N6—Ti1—N7—C274.71 (13)N7—C28—C29—N81.5 (3)
N2—Ti1—N7—C27145.27 (13)N8—C29—C30—C310.1 (3)
N3—Ti1—N7—C2786.85 (16)C28—C29—C30—C31179.6 (2)
N4—Ti1—N7—C2789.70 (14)C29—C30—C31—C320.3 (3)
N5—Ti1—N7—C2738.10 (16)C29—N8—C32—C310.4 (2)
N1—Ti1—N8—C3297.85 (19)Ti1—N8—C32—C31172.18 (15)
N6—Ti1—N8—C32169.32 (17)C30—C31—C32—N80.5 (3)
N2—Ti1—N8—C3222.76 (19)C36—O1—C33—C3412.5 (5)
N3—Ti1—N8—C3241.0 (2)O1—C33—C34—C3519.3 (5)
N7—Ti1—N8—C32176.3 (2)C33—C34—C35—C3618.2 (4)
N4—Ti1—N8—C32108.3 (2)C33—O1—C36—C350.4 (4)
N5—Ti1—N8—C3246.2 (2)C34—C35—C36—O111.5 (4)
N1—Ti1—N8—C2973.27 (14)

Experimental details

Crystal data
Chemical formula[Ti(C16H18N4)2]·C4H8O
Mr652.69
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)15.7746 (11), 8.7372 (6), 23.5824 (16)
β (°) 90.214 (1)
V3)3250.2 (4)
Z4
Radiation typeMo Kα
µ (mm1)0.31
Crystal size (mm)0.44 × 0.34 × 0.24
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.877, 0.931
No. of measured, independent and
observed [I > 2σ(I)] reflections
23461, 6052, 4955
Rint0.026
(sin θ/λ)max1)0.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.101, 1.03
No. of reflections6052
No. of parameters415
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.31, 0.29

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top
Ti1—N12.1289 (16)Ti1—N52.2929 (16)
Ti1—N22.2283 (15)Ti1—N62.2234 (15)
Ti1—N32.2344 (16)Ti1—N72.2593 (16)
Ti1—N42.2706 (16)Ti1—N82.1647 (16)
 

Acknowledgements

The authors gratefully acknowledge financial support from the Hundreds of Talents Program (grant No. 2005012) of the Chinese Academy of Sciences and the Science Foundation of Qinghai Province, China (grant No. 2006-G-105).

References

First citationGardner, J. D., Robson, D. A., Rees, L. H. & Mountford, P. (2001). Inorg. Chem. 40, 820–824.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationHan, X. Y., Li, Y. H., Wei, H. & Zhang, Y. (2007). Chin. J. Chem. 25, 1334–1339.  Web of Science CSD CrossRef CAS Google Scholar
First citationLi, Y. H., Turnas, A., Ciszewski, J. T. & Odom, A. L. (2002). Inorg. Chem. 41, 6298–6306.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSiemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.  Google Scholar

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