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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2010 Dec 24;67(Pt 1):m125. doi: 10.1107/S1600536810053262

Dichlorido(N,N′-diisopropyl­piperidine-1-carboximidamidato-κ2 N,N′)titanium(IV)

Mei Wang a, Ying-Ming Yao b, Yong Zhang b, Zhen-Qin Zhang c,*, Li-Ying Shi c
PMCID: PMC3050264  PMID: 21522536

Abstract

In the mononuclear title complex, [Ti(C12H24N3)2Cl2], the TiIV ion, located on a crystallographic inversion center, is six-coordinated by four N atoms from two N′,N′′-diisopropyl-N-carboxamidine anions and two chloride atoms in a distorted octahedral geometry. The dihedral angles between the piperidine groups and the NCN chelate rings are 51.5 (1) and 52.3 (1)°.

Related literature

For background to the coordination chemistry of guanidinates, see: Braunschweig et al. (2010 ▶). For the synthesis of similar compounds, see: Bailey et al. (2000 ▶); Mullins et al. (2001 ▶). graphic file with name e-67-0m125-scheme1.jpg

Experimental

Crystal data

  • [Ti(C12H24N3)2Cl2]

  • M r = 539.48

  • Triclinic, Inline graphic

  • a = 8.2810 (3) Å

  • b = 13.3678 (9) Å

  • c = 13.6178 (7) Å

  • α = 86.266 (10)°

  • β = 75.841 (8)°

  • γ = 82.304 (8)°

  • V = 1447.69 (13) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.50 mm−1

  • T = 193 K

  • 0.70 × 0.25 × 0.15 mm

Data collection

  • Rigaku Mercury diffractometer

  • Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T min = 0.720, T max = 0.928

  • 14490 measured reflections

  • 6513 independent reflections

  • 5896 reflections with I > 2σ(I)

  • R int = 0.024

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041

  • wR(F 2) = 0.097

  • S = 1.08

  • 6513 reflections

  • 306 parameters

  • H-atom parameters constrained

  • Δρmax = 0.64 e Å−3

  • Δρmin = −0.32 e Å−3

Data collection: CrystalClear (Rigaku, 1999 ▶); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: CrystalStructure.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810053262/hg2762sup1.cif

e-67-0m125-sup1.cif (29.2KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810053262/hg2762Isup2.hkl

e-67-0m125-Isup2.hkl (318.7KB, hkl)

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

Acknowledgments

Financial support from the Science Foundation of Jiangpu Senior Middle School is gratefully acknowledged.

supplementary crystallographic information

Comment

Guanidinate anions, [(RN)2C(NR'2)]-, are isoelectronic alternatives to cyclopentadienyl ligands and modifications to their electronic properties and steric bulk can be investigated through variation of the substiuents on the nitrogen atoms. As a result, guanidinate ligands have been attacted increasing attention as ancillary ligands in the coordination and organometallic chemistry of main group and transition metals (Braunschweig et al., 2010). As part of our ongoing investigations in this field we report here the crystal structure of the title compound. In the crystal structure of the title compound the Ti atom is coordinated by four nitrogen atoms of two guanidinate ligands and two chloride atoms within a triclinic coordination symmetry (Figure 1).

The Ti—N bond lengths vary from 2.0125 (14) to 2.1299 (14)Å, which are close to the values reported for [Et2NC(NPh)2]2TiCl2 (Bailey et al., 2000) and [Et2NC(NiPr)2]2TiCl2 and [Et2NC(NiPr)2]2TiS2 (Mullins et al., 2001). The bond lengths of Ti—Cl of 2.3254 (5) and 2.3308 (6)Å are comparable with those in [Et2NC(NPh)2]2TiCl2 and [Et2NC(NiPr)2]2TiCl2. The bond distance around N(1), C(1), N(2) and N(4), C(13), N(5) average 1.342Å indicating partial double-bonding character and a π-conjugated NCN chelate. The bond angles around N(3) and N(6) ranging from 113.9 (1) to 124.5 (1)° consistent with sp2-hybridized nitrogen atoms. The dihedral angles between the piperidine groups and the NCN chelate rings are 51.5 and 52.3°.

Experimental

A solution of n-butyllithium (8.40 ml, 10 mmol) in hexane was added via syringe to a THF solution of piperidine (10 mmol) at -78°C. The solution was warmed to room temperature slowly and stirred for 30 min. Then N-((isopropylimino)methylene)propan-2-amine (1.26 g, 10 mmol) was added via syringe at 0°C. The mixture was stirred at room temperature (r.t.) for 30 min, then was added to a suspension of TiCl4(THF)2 (1.65 g, 5 mmol) in toluene (20 ml) at r.t. The reaction mixture was stirred overnight at r.t. After removal of volatiles under vacuum, the dark red residue was extracted with toluene, and LiCl was removed by centrifugation. The dark red crystals were obtained from concentrated toluene solution at -10°C. Anal. Calcd. for C24H48Cl2N6Ti: C, 53.50; H, 8.91; N, 15.59. Found: C, 53.81; H, 9.58; N, 15.86%.

Refinement

H atoms of the methyl groups were placed geometrically with C—H = 0.97 Å and allowed to ride during subsequent refinement with Uiso(H) = 1.5Ueq(C). Fifteen missing reflections appeared to be obscured by the beamstop.

Figures

Fig. 1.

Fig. 1.

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Crystal structure and atom numbering of the title compound, shown with 30% probability displacement ellipsoids.

Crystal data

[Ti(C12H24N3)2Cl2] Z = 2
Mr = 539.48 F(000) = 580
Triclinic, P1 Dx = 1.238 Mg m−3
Hall symbol: -P 1 Mo Kα radiation, λ = 0.71070 Å
a = 8.2810 (3) Å Cell parameters from 3913 reflections
b = 13.3678 (9) Å θ = 3.1–27.5°
c = 13.6178 (7) Å µ = 0.50 mm−1
α = 86.266 (10)° T = 193 K
β = 75.841 (8)° Block, dark-red
γ = 82.304 (8)° 0.70 × 0.25 × 0.15 mm
V = 1447.69 (13) Å3
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Data collection

Rigaku Mercury diffractometer 6513 independent reflections
Radiation source: fine-focus sealed tube 5896 reflections with I > 2σ(I)
graphite Rint = 0.024
Detector resolution: 14.62 pixels mm-1 θmax = 27.5°, θmin = 3.1°
ω scans h = −10→10
Absorption correction: multi-scan (REQAB; Jacobson, 1998) k = −17→17
Tmin = 0.720, Tmax = 0.928 l = −16→17
14490 measured reflections
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Refinement

Refinement on F2 Primary atom site location: structure-invariant direct methods
Least-squares matrix: full Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097 H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0406P)2 + 0.8209P] where P = (Fo2 + 2Fc2)/3
6513 reflections (Δ/σ)max < 0.001
306 parameters Δρmax = 0.64 e Å−3
0 restraints Δρmin = −0.32 e Å−3
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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.
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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq
Ti1 0.02434 (4) 0.22060 (2) 0.23396 (2) 0.02022 (8)
Cl1 −0.06242 (6) 0.23150 (3) 0.08319 (4) 0.03338 (12)
Cl2 −0.22892 (6) 0.17162 (4) 0.32905 (4) 0.03487 (12)
N1 −0.04278 (17) 0.36915 (10) 0.27568 (11) 0.0234 (3)
N2 0.20565 (17) 0.31810 (10) 0.17994 (11) 0.0227 (3)
N3 0.12949 (17) 0.49848 (10) 0.20127 (12) 0.0255 (3)
N4 0.16572 (17) 0.08674 (10) 0.20244 (10) 0.0194 (3)
N5 0.15650 (17) 0.15914 (10) 0.34437 (10) 0.0216 (3)
N6 0.34501 (17) 0.00317 (11) 0.30397 (10) 0.0223 (3)
C1 0.0996 (2) 0.39864 (12) 0.21722 (13) 0.0218 (3)
C2 −0.1776 (2) 0.43961 (13) 0.33551 (14) 0.0278 (4)
H2 −0.1393 0.5081 0.3280 0.033*
C3 −0.3349 (2) 0.44610 (17) 0.29507 (18) 0.0405 (5)
H3A −0.3080 0.4662 0.2230 0.061*
H3B −0.4214 0.4962 0.3326 0.061*
H3C −0.3764 0.3800 0.3036 0.061*
C4 −0.2153 (3) 0.40813 (17) 0.44766 (15) 0.0408 (5)
H4A −0.2479 0.3397 0.4563 0.061*
H4B −0.3073 0.4551 0.4853 0.061*
H4C −0.1150 0.4094 0.4735 0.061*
C5 0.3538 (2) 0.32465 (15) 0.09379 (15) 0.0329 (4)
H5 0.4166 0.3781 0.1095 0.039*
C6 0.3042 (3) 0.3572 (2) −0.00399 (17) 0.0558 (7)
H6A 0.2423 0.3064 −0.0220 0.084*
H6B 0.4052 0.3641 −0.0580 0.084*
H6C 0.2328 0.4222 0.0045 0.084*
C7 0.4687 (3) 0.2273 (2) 0.0867 (2) 0.0675 (9)
H7A 0.4964 0.2101 0.1522 0.101*
H7B 0.5718 0.2347 0.0346 0.101*
H7C 0.4129 0.1734 0.0687 0.101*
C8 0.0227 (2) 0.57243 (13) 0.15365 (14) 0.0288 (4)
H8A −0.0868 0.5475 0.1600 0.035*
H8B 0.0762 0.5804 0.0806 0.035*
C9 −0.0054 (2) 0.67433 (14) 0.20283 (17) 0.0350 (4)
H9A −0.0738 0.6687 0.2731 0.042*
H9B −0.0678 0.7247 0.1648 0.042*
C10 0.1618 (3) 0.70969 (14) 0.20385 (16) 0.0351 (4)
H10A 0.2226 0.7255 0.1336 0.042*
H10B 0.1411 0.7721 0.2427 0.042*
C11 0.2692 (3) 0.62867 (14) 0.25152 (16) 0.0349 (4)
H11A 0.2144 0.6185 0.3241 0.042*
H11B 0.3799 0.6512 0.2471 0.042*
C12 0.2936 (2) 0.52900 (14) 0.19807 (16) 0.0319 (4)
H12A 0.3567 0.5372 0.1268 0.038*
H12B 0.3589 0.4764 0.2321 0.038*
C13 0.22731 (19) 0.08123 (12) 0.28716 (12) 0.0192 (3)
C14 0.1624 (2) −0.00526 (12) 0.14861 (13) 0.0234 (3)
H14 0.2350 −0.0617 0.1743 0.028*
C15 −0.0156 (2) −0.03373 (14) 0.17258 (15) 0.0310 (4)
H15A −0.0539 −0.0470 0.2457 0.046*
H15B −0.0170 −0.0945 0.1364 0.046*
H15C −0.0904 0.0220 0.1511 0.046*
C16 0.2324 (3) 0.00808 (16) 0.03502 (14) 0.0353 (4)
H16A 0.1663 0.0651 0.0086 0.053*
H16B 0.2267 −0.0536 0.0015 0.053*
H16C 0.3495 0.0213 0.0218 0.053*
C17 0.2158 (2) 0.18903 (14) 0.43013 (13) 0.0281 (4)
H17 0.3158 0.1406 0.4370 0.034*
C18 0.0777 (3) 0.18062 (18) 0.52705 (14) 0.0398 (5)
H18A −0.0252 0.2224 0.5191 0.060*
H18B 0.1135 0.2040 0.5842 0.060*
H18C 0.0563 0.1100 0.5400 0.060*
C19 0.2684 (3) 0.29504 (16) 0.41280 (17) 0.0398 (5)
H19A 0.3570 0.2976 0.3503 0.060*
H19B 0.3105 0.3119 0.4702 0.060*
H19C 0.1714 0.3437 0.4067 0.060*
C20 0.4988 (2) −0.01999 (13) 0.22347 (13) 0.0265 (4)
H20A 0.5903 0.0133 0.2375 0.032*
H20B 0.4786 0.0075 0.1577 0.032*
C21 0.5530 (2) −0.13335 (14) 0.21646 (14) 0.0315 (4)
H21A 0.4696 −0.1656 0.1924 0.038*
H21B 0.6625 −0.1459 0.1669 0.038*
C22 0.5683 (2) −0.17964 (16) 0.31945 (16) 0.0366 (4)
H22A 0.6621 −0.1541 0.3394 0.044*
H22B 0.5932 −0.2540 0.3152 0.044*
C23 0.4055 (3) −0.15274 (15) 0.39905 (15) 0.0369 (4)
H23A 0.4191 −0.1805 0.4662 0.044*
H23B 0.3141 −0.1839 0.3823 0.044*
C24 0.3581 (3) −0.03855 (15) 0.40407 (13) 0.0330 (4)
H24A 0.2495 −0.0230 0.4537 0.040*
H24B 0.4445 −0.0076 0.4266 0.040*
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Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
Ti1 0.01973 (15) 0.01908 (15) 0.02277 (16) −0.00208 (11) −0.00691 (11) −0.00083 (11)
Cl1 0.0400 (3) 0.0334 (2) 0.0332 (2) −0.00592 (19) −0.0216 (2) 0.00408 (18)
Cl2 0.0250 (2) 0.0379 (2) 0.0392 (3) −0.00926 (18) 0.00079 (18) −0.0037 (2)
N1 0.0179 (6) 0.0208 (7) 0.0295 (8) −0.0010 (5) −0.0023 (6) −0.0025 (6)
N2 0.0198 (7) 0.0215 (7) 0.0248 (7) −0.0015 (5) −0.0023 (5) −0.0006 (5)
N3 0.0210 (7) 0.0194 (7) 0.0380 (8) −0.0030 (5) −0.0114 (6) 0.0032 (6)
N4 0.0210 (6) 0.0203 (6) 0.0184 (6) −0.0015 (5) −0.0082 (5) −0.0010 (5)
N5 0.0222 (7) 0.0257 (7) 0.0186 (7) −0.0027 (5) −0.0075 (5) −0.0033 (5)
N6 0.0213 (7) 0.0280 (7) 0.0172 (7) 0.0015 (5) −0.0065 (5) 0.0011 (5)
C1 0.0211 (8) 0.0212 (8) 0.0248 (8) −0.0020 (6) −0.0090 (6) −0.0007 (6)
C2 0.0222 (8) 0.0250 (8) 0.0327 (9) 0.0023 (7) −0.0017 (7) −0.0043 (7)
C3 0.0208 (9) 0.0439 (12) 0.0536 (13) 0.0020 (8) −0.0062 (9) −0.0008 (10)
C4 0.0407 (11) 0.0410 (11) 0.0324 (11) 0.0045 (9) 0.0030 (9) −0.0046 (9)
C5 0.0255 (9) 0.0319 (9) 0.0355 (10) −0.0036 (7) 0.0033 (8) −0.0003 (8)
C6 0.0425 (13) 0.088 (2) 0.0304 (11) −0.0109 (13) 0.0037 (10) 0.0027 (12)
C7 0.0363 (13) 0.0521 (15) 0.087 (2) 0.0078 (11) 0.0249 (13) 0.0141 (14)
C8 0.0292 (9) 0.0262 (9) 0.0326 (9) −0.0020 (7) −0.0129 (8) 0.0056 (7)
C9 0.0336 (10) 0.0228 (9) 0.0473 (12) 0.0004 (7) −0.0105 (9) 0.0038 (8)
C10 0.0402 (11) 0.0210 (8) 0.0439 (11) −0.0056 (8) −0.0091 (9) 0.0010 (8)
C11 0.0359 (10) 0.0274 (9) 0.0461 (12) −0.0084 (8) −0.0164 (9) −0.0005 (8)
C12 0.0243 (9) 0.0257 (9) 0.0475 (11) −0.0062 (7) −0.0112 (8) 0.0015 (8)
C13 0.0177 (7) 0.0228 (8) 0.0180 (7) −0.0052 (6) −0.0051 (6) 0.0018 (6)
C14 0.0262 (8) 0.0208 (8) 0.0260 (8) 0.0000 (6) −0.0123 (7) −0.0036 (6)
C15 0.0331 (9) 0.0257 (9) 0.0399 (11) −0.0074 (7) −0.0176 (8) −0.0008 (7)
C16 0.0387 (10) 0.0429 (11) 0.0251 (9) 0.0011 (9) −0.0094 (8) −0.0110 (8)
C17 0.0279 (9) 0.0350 (9) 0.0250 (9) 0.0000 (7) −0.0132 (7) −0.0086 (7)
C18 0.0432 (11) 0.0547 (13) 0.0212 (9) 0.0020 (10) −0.0097 (8) −0.0078 (9)
C19 0.0419 (11) 0.0403 (11) 0.0456 (12) −0.0074 (9) −0.0219 (10) −0.0131 (9)
C20 0.0200 (8) 0.0308 (9) 0.0278 (9) −0.0030 (7) −0.0054 (7) 0.0034 (7)
C21 0.0239 (9) 0.0341 (10) 0.0328 (10) 0.0037 (7) −0.0036 (7) −0.0002 (8)
C22 0.0316 (10) 0.0347 (10) 0.0418 (11) 0.0062 (8) −0.0127 (9) 0.0052 (8)
C23 0.0423 (11) 0.0366 (10) 0.0279 (10) 0.0036 (9) −0.0079 (8) 0.0089 (8)
C24 0.0405 (10) 0.0382 (10) 0.0203 (9) 0.0033 (8) −0.0127 (8) 0.0028 (7)
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Geometric parameters (Å, °)

Ti1—N4 2.0125 (14) C9—C10 1.525 (3)
Ti1—N1 2.0669 (14) C9—H9A 0.9900
Ti1—N2 2.0864 (14) C9—H9B 0.9900
Ti1—N5 2.1299 (14) C10—C11 1.522 (3)
Ti1—Cl1 2.3254 (5) C10—H10A 0.9900
Ti1—Cl2 2.3308 (6) C10—H10B 0.9900
Ti1—C1 2.5224 (17) C11—C12 1.526 (3)
Ti1—C13 2.5303 (16) C11—H11A 0.9900
N1—C1 1.343 (2) C11—H11B 0.9900
N1—C2 1.473 (2) C12—H12A 0.9900
N2—C1 1.337 (2) C12—H12B 0.9900
N2—C5 1.483 (2) C14—C16 1.521 (2)
N3—C1 1.383 (2) C14—C15 1.524 (2)
N3—C12 1.461 (2) C14—H14 1.0000
N3—C8 1.464 (2) C15—H15A 0.9800
N4—C13 1.365 (2) C15—H15B 0.9800
N4—C14 1.479 (2) C15—H15C 0.9800
N5—C13 1.324 (2) C16—H16A 0.9800
N5—C17 1.469 (2) C16—H16B 0.9800
N6—C13 1.377 (2) C16—H16C 0.9800
N6—C24 1.462 (2) C17—C19 1.525 (3)
N6—C20 1.475 (2) C17—C18 1.529 (3)
C2—C3 1.523 (3) C17—H17 1.0000
C2—C4 1.525 (3) C18—H18A 0.9800
C2—H2 1.0000 C18—H18B 0.9800
C3—H3A 0.9800 C18—H18C 0.9800
C3—H3B 0.9800 C19—H19A 0.9800
C3—H3C 0.9800 C19—H19B 0.9800
C4—H4A 0.9800 C19—H19C 0.9800
C4—H4B 0.9800 C20—C21 1.524 (3)
C4—H4C 0.9800 C20—H20A 0.9900
C5—C7 1.500 (3) C20—H20B 0.9900
C5—C6 1.508 (3) C21—C22 1.523 (3)
C5—H5 1.0000 C21—H21A 0.9900
C6—H6A 0.9800 C21—H21B 0.9900
C6—H6B 0.9800 C22—C23 1.526 (3)
C6—H6C 0.9800 C22—H22A 0.9900
C7—H7A 0.9800 C22—H22B 0.9900
C7—H7B 0.9800 C23—C24 1.526 (3)
C7—H7C 0.9800 C23—H23A 0.9900
C8—C9 1.522 (3) C23—H23B 0.9900
C8—H8A 0.9900 C24—H24A 0.9900
C8—H8B 0.9900 C24—H24B 0.9900
N4—Ti1—N1 159.82 (6) C8—C9—H9A 109.5
N4—Ti1—N2 100.06 (6) C10—C9—H9A 109.5
N1—Ti1—N2 63.86 (5) C8—C9—H9B 109.5
N4—Ti1—N5 64.01 (5) C10—C9—H9B 109.5
N1—Ti1—N5 102.08 (6) H9A—C9—H9B 108.1
N2—Ti1—N5 89.81 (5) C11—C10—C9 110.83 (15)
N4—Ti1—Cl1 93.71 (4) C11—C10—H10A 109.5
N1—Ti1—Cl1 99.11 (4) C9—C10—H10A 109.5
N2—Ti1—Cl1 93.32 (4) C11—C10—H10B 109.5
N5—Ti1—Cl1 157.69 (4) C9—C10—H10B 109.5
N4—Ti1—Cl2 102.08 (4) H10A—C10—H10B 108.1
N1—Ti1—Cl2 92.76 (4) C10—C11—C12 110.97 (16)
N2—Ti1—Cl2 156.46 (4) C10—C11—H11A 109.4
N5—Ti1—Cl2 92.70 (4) C12—C11—H11A 109.4
Cl1—Ti1—Cl2 93.17 (2) C10—C11—H11B 109.4
N4—Ti1—C1 131.72 (5) C12—C11—H11B 109.4
N1—Ti1—C1 32.13 (5) H11A—C11—H11B 108.0
N2—Ti1—C1 31.98 (5) N3—C12—C11 109.07 (15)
N5—Ti1—C1 99.88 (5) N3—C12—H12A 109.9
Cl1—Ti1—C1 94.34 (4) C11—C12—H12A 109.9
Cl2—Ti1—C1 124.85 (4) N3—C12—H12B 109.9
N4—Ti1—C13 32.50 (5) C11—C12—H12B 109.9
N1—Ti1—C13 131.67 (6) H12A—C12—H12B 108.3
N2—Ti1—C13 94.39 (5) N5—C13—N4 109.59 (14)
N5—Ti1—C13 31.56 (5) N5—C13—N6 128.95 (14)
Cl1—Ti1—C13 126.14 (4) N4—C13—N6 121.46 (14)
Cl2—Ti1—C13 99.95 (4) N5—C13—Ti1 57.31 (8)
C1—Ti1—C13 118.19 (5) N4—C13—Ti1 52.39 (8)
C1—N1—C2 123.07 (14) N6—C13—Ti1 173.14 (12)
C1—N1—Ti1 92.95 (10) N4—C14—C16 111.48 (14)
C2—N1—Ti1 143.91 (11) N4—C14—C15 109.93 (14)
C1—N2—C5 123.23 (14) C16—C14—C15 111.42 (15)
C1—N2—Ti1 92.28 (10) N4—C14—H14 108.0
C5—N2—Ti1 137.87 (12) C16—C14—H14 108.0
C1—N3—C12 121.71 (14) C15—C14—H14 108.0
C1—N3—C8 121.35 (14) C14—C15—H15A 109.5
C12—N3—C8 113.86 (14) C14—C15—H15B 109.5
C13—N4—C14 121.05 (13) H15A—C15—H15B 109.5
C13—N4—Ti1 95.10 (10) C14—C15—H15C 109.5
C14—N4—Ti1 137.93 (10) H15A—C15—H15C 109.5
C13—N5—C17 124.45 (14) H15B—C15—H15C 109.5
C13—N5—Ti1 91.13 (10) C14—C16—H16A 109.5
C17—N5—Ti1 141.22 (11) C14—C16—H16B 109.5
C13—N6—C24 124.54 (14) H16A—C16—H16B 109.5
C13—N6—C20 118.69 (13) C14—C16—H16C 109.5
C24—N6—C20 113.94 (14) H16A—C16—H16C 109.5
N2—C1—N1 110.09 (14) H16B—C16—H16C 109.5
N2—C1—N3 126.28 (15) N5—C17—C19 111.43 (15)
N1—C1—N3 123.62 (15) N5—C17—C18 108.81 (15)
N2—C1—Ti1 55.74 (8) C19—C17—C18 111.69 (17)
N1—C1—Ti1 54.92 (8) N5—C17—H17 108.3
N3—C1—Ti1 173.93 (12) C19—C17—H17 108.3
N1—C2—C3 110.11 (15) C18—C17—H17 108.3
N1—C2—C4 111.19 (15) C17—C18—H18A 109.5
C3—C2—C4 110.72 (17) C17—C18—H18B 109.5
N1—C2—H2 108.2 H18A—C18—H18B 109.5
C3—C2—H2 108.2 C17—C18—H18C 109.5
C4—C2—H2 108.2 H18A—C18—H18C 109.5
C2—C3—H3A 109.5 H18B—C18—H18C 109.5
C2—C3—H3B 109.5 C17—C19—H19A 109.5
H3A—C3—H3B 109.5 C17—C19—H19B 109.5
C2—C3—H3C 109.5 H19A—C19—H19B 109.5
H3A—C3—H3C 109.5 C17—C19—H19C 109.5
H3B—C3—H3C 109.5 H19A—C19—H19C 109.5
C2—C4—H4A 109.5 H19B—C19—H19C 109.5
C2—C4—H4B 109.5 N6—C20—C21 111.62 (14)
H4A—C4—H4B 109.5 N6—C20—H20A 109.3
C2—C4—H4C 109.5 C21—C20—H20A 109.3
H4A—C4—H4C 109.5 N6—C20—H20B 109.3
H4B—C4—H4C 109.5 C21—C20—H20B 109.3
N2—C5—C7 110.00 (16) H20A—C20—H20B 108.0
N2—C5—C6 112.07 (16) C22—C21—C20 110.55 (16)
C7—C5—C6 113.2 (2) C22—C21—H21A 109.5
N2—C5—H5 107.1 C20—C21—H21A 109.5
C7—C5—H5 107.1 C22—C21—H21B 109.5
C6—C5—H5 107.1 C20—C21—H21B 109.5
C5—C6—H6A 109.5 H21A—C21—H21B 108.1
C5—C6—H6B 109.5 C21—C22—C23 110.28 (15)
H6A—C6—H6B 109.5 C21—C22—H22A 109.6
C5—C6—H6C 109.5 C23—C22—H22A 109.6
H6A—C6—H6C 109.5 C21—C22—H22B 109.6
H6B—C6—H6C 109.5 C23—C22—H22B 109.6
C5—C7—H7A 109.5 H22A—C22—H22B 108.1
C5—C7—H7B 109.5 C22—C23—C24 111.17 (17)
H7A—C7—H7B 109.5 C22—C23—H23A 109.4
C5—C7—H7C 109.5 C24—C23—H23A 109.4
H7A—C7—H7C 109.5 C22—C23—H23B 109.4
H7B—C7—H7C 109.5 C24—C23—H23B 109.4
N3—C8—C9 111.14 (15) H23A—C23—H23B 108.0
N3—C8—H8A 109.4 N6—C24—C23 109.52 (15)
C9—C8—H8A 109.4 N6—C24—H24A 109.8
N3—C8—H8B 109.4 C23—C24—H24A 109.8
C9—C8—H8B 109.4 N6—C24—H24B 109.8
H8A—C8—H8B 108.0 C23—C24—H24B 109.8
C8—C9—C10 110.60 (16) H24A—C24—H24B 108.2
N4—Ti1—N1—C1 45.1 (2) Ti1—N1—C1—N2 −8.40 (14)
N2—Ti1—N1—C1 5.62 (9) C2—N1—C1—N3 −4.8 (3)
N5—Ti1—N1—C1 89.37 (10) Ti1—N1—C1—N3 172.86 (14)
Cl1—Ti1—N1—C1 −83.61 (10) C8—N3—C1—N2 120.40 (19)
Cl2—Ti1—N1—C1 −177.27 (9) C12—N3—C1—N1 139.97 (18)
N4—Ti1—N1—C2 −138.13 (19) C8—N3—C1—N1 −61.1 (2)
N2—Ti1—N1—C2 −177.7 (2) C1—N1—C2—C3 114.12 (18)
N5—Ti1—N1—C2 −93.9 (2) Ti1—N1—C2—C3 −62.0 (3)
Cl1—Ti1—N1—C2 93.1 (2) C1—N1—C2—C4 −122.78 (19)
Cl2—Ti1—N1—C2 −0.5 (2) Ti1—N1—C2—C4 61.1 (3)
C1—Ti1—N1—C2 176.7 (3) C1—N2—C5—C7 166.3 (2)
N4—Ti1—N2—C1 −172.76 (10) Ti1—N2—C5—C7 −51.1 (3)
N1—Ti1—N2—C1 −5.64 (9) C1—N2—C5—C6 −66.9 (2)
N5—Ti1—N2—C1 −109.22 (10) Ti1—N2—C5—C6 75.8 (2)
Cl1—Ti1—N2—C1 92.88 (9) C1—N3—C8—C9 141.66 (17)
Cl2—Ti1—N2—C1 −12.88 (17) C12—N3—C8—C9 −57.8 (2)
N4—Ti1—N2—C5 37.75 (18) N3—C8—C9—C10 53.3 (2)
N1—Ti1—N2—C5 −155.13 (19) C8—C9—C10—C11 −52.9 (2)
N5—Ti1—N2—C5 101.29 (17) C9—C10—C11—C12 55.2 (2)
Cl1—Ti1—N2—C5 −56.61 (17) C1—N3—C12—C11 −140.78 (17)
Cl2—Ti1—N2—C5 −162.37 (13) C8—N3—C12—C11 58.8 (2)
C1—Ti1—N2—C5 −149.5 (2) C10—C11—C12—N3 −56.7 (2)
N1—Ti1—N4—C13 46.9 (2) C17—N5—C13—N4 −167.17 (15)
N2—Ti1—N4—C13 82.33 (10) Ti1—N5—C13—N4 −3.61 (12)
N5—Ti1—N4—C13 −2.50 (9) C17—N5—C13—N6 13.0 (3)
Cl1—Ti1—N4—C13 176.36 (9) Ti1—N5—C13—N6 176.54 (15)
Cl2—Ti1—N4—C13 −89.59 (9) C14—N4—C13—N5 −153.63 (14)
C1—Ti1—N4—C13 77.19 (11) Ti1—N4—C13—N5 3.84 (13)
N1—Ti1—N4—C14 −162.48 (16) C14—N4—C13—N6 26.2 (2)
N2—Ti1—N4—C14 −127.01 (16) Ti1—N4—C13—N6 −176.30 (13)
N5—Ti1—N4—C14 148.17 (18) C14—N4—C13—Ti1 −157.47 (16)
Cl1—Ti1—N4—C14 −32.97 (16) C24—N6—C13—N5 31.7 (3)
Cl2—Ti1—N4—C14 61.07 (16) C20—N6—C13—N5 −128.08 (18)
C1—Ti1—N4—C14 −132.14 (15) C24—N6—C13—N4 −148.16 (16)
N4—Ti1—N5—C13 2.57 (9) C20—N6—C13—N4 52.1 (2)
N1—Ti1—N5—C13 −161.90 (9) C13—N4—C14—C16 −132.18 (16)
N2—Ti1—N5—C13 −98.73 (10) Ti1—N4—C14—C16 82.54 (19)
Cl1—Ti1—N5—C13 −0.42 (17) C13—N4—C14—C15 103.75 (17)
Cl2—Ti1—N5—C13 104.69 (9) Ti1—N4—C14—C15 −41.5 (2)
C1—Ti1—N5—C13 −129.24 (10) C13—N5—C17—C19 118.58 (18)
N4—Ti1—N5—C17 160.7 (2) Ti1—N5—C17—C19 −34.6 (3)
N1—Ti1—N5—C17 −3.78 (19) C13—N5—C17—C18 −117.83 (18)
N2—Ti1—N5—C17 59.40 (18) Ti1—N5—C17—C18 89.0 (2)
Cl1—Ti1—N5—C17 157.70 (14) C13—N6—C20—C21 −142.13 (15)
Cl2—Ti1—N5—C17 −97.19 (18) C24—N6—C20—C21 56.0 (2)
C13—Ti1—N5—C17 158.1 (2) N6—C20—C21—C22 −53.4 (2)
C5—N2—C1—N1 164.29 (15) C20—C21—C22—C23 54.0 (2)
Ti1—N2—C1—N1 8.32 (14) C21—C22—C23—C24 −56.3 (2)
C5—N2—C1—N3 −17.0 (3) C13—N6—C24—C23 142.54 (17)
Ti1—N2—C1—N3 −172.98 (15) C20—N6—C24—C23 −56.9 (2)
C2—N1—C1—N2 173.91 (15) C22—C23—C24—N6 56.7 (2)
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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2762).

References

  1. Bailey, P. J., Grant, K. J., Mitchell, L. A., Pace, S., Parkin, A. & Parsons, S. (2000). J. Chem. Soc. Dalton Trans. pp. 1887–1891.
  2. Braunschweig, H., Dewhurst, R. D., Schwab, K. & Wagner, K. (2010). Acta Cryst. E66, o610. [DOI] [PMC free article] [PubMed]
  3. Burnett, M. & Johnson, C. K. (1996). ORTEPIII Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
  4. Jacobson, R. (1998). REQAB Private communication to the Rigaku Corporation, Tokyo, Japan.
  5. Mullins, S. M., Duncan, A. P., Bergman, R. G. & Arnold, J. (2001). Inorg. Chem. 40, 6952–6963. [DOI] [PubMed]
  6. Rigaku (1999). CrystalClear Rigaku Corporation, Tokyo, Japan.
  7. Rigaku/MSC (2002). CrystalStructure Rigaku/MSC, The Woodlands, Texas, USA.
  8. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810053262/hg2762sup1.cif

e-67-0m125-sup1.cif (29.2KB, cif)

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810053262/hg2762Isup2.hkl

e-67-0m125-Isup2.hkl (318.7KB, hkl)

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

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

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