Bis(μ-N-(3-[3-indenyl]­propyl-p-toluene­sulf­amido-N,O,O′)-di­methyl­amido­dichorotitanium)

Lensink, C.; Gainsford, G.J.; Brandsma, M.J.R.

doi:10.1107/S1600536802015787

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Bis(μ-N-(3-[3-indenyl]propyl-p-toluenesulfamido-N,O,O′)-dimethylamidodichorotitanium)

C. Lensink, G. J. Gainsford and M. J. R. Brandsma

The title compound, [Ti(C₂₁H₂₆N₂O₂S)Cl₂], crystallizes as a centrosymmetric dimer, with an eight-membered ring derived from the monomer sub-units by the formation of two Ti—(N,O)—S—O head-to-tail sequences around a crystallographic inversion centre. The titanium atoms each have a distorted octahedral geometry through the nitrogen and one oxygen of the sulfonamido group [Ti1—O1, Ti—N1 2.280 (3), 2.091 (3) Å], one oxygen from the adjacent sulfonamide [Ti—O2 2.170 (3) Å], a dimethylamido nitrogen and two chlorides.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802015787/tk6076sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536802015787/tk6076Isup2.hkl Contains datablock I

CCDC reference: 140435

checkCIF report

Key indicators

Single-crystal X-ray study
T = 170 K
Mean (C-C) = 0.007 Å
R factor = 0.052
wR factor = 0.140
Data-to-parameter ratio = 17.6

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level B:



ABSTM_02  Alert B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
          Tmin and Tmax reported:      0.393     0.892
          Tmin' and Tmax expected:      0.771     0.892
          RR' =      0.510
          Please check that your absorption correction is appropriate.

Author response: The ratio given is that given in summary after the SADABS run; It seems possible that the smallest dimension is inaccurate, but the crystal is no longer available to be re-measured.


 0 Alert Level A = Potentially serious problem

 1 Alert Level B = Potential problem

 0 Alert Level C = Please check

Comment top

The title compound, which is related to previously reported structures (Lensink, 1998, Lensink et al., 2001), crystallizes as a centrosymmetric dimer with an eight-membered ring derived from the monomer sub-units by the formation of two Ti—(N,O)—S—O head-to-tail sequences around a crystallographic inversion centre (Fig. 1; Table 1). There are no significant intermolecular contacts in the crystal structure. The titanium atoms have a distorted octahedral geometry through the nitrogen and one oxygen of the sulfonamido group [Ti1—O1, Ti—N1 2.280 (3), 2.091 (3) Å], one oxygen from the adjacent sulfonamide [Ti—O2 2.170 (3) Å], a dimethylamido nitrogen and two chlorides. A similar ring structure has been reported for the yttrium compound, Bis((µ₂-trans-1,2-bis(2,4,6-tri-isopropylbenzene-sulfonamidato)cyclo hexane-N,N',O,O',O'')-bis(methylsilyl)-amido-yttrium(III)) (Goerlitzer et al., 1998).

The Ti—N2 bond distance of 1.860 (4) Å is consistent with N(pπ\)–M(dπ\) interaction expected for a dimethylamide, and the Ti—Cl bond distances and relative geometries are similar to those found in dichloro-(4-methyl-2-(trimethylsilylamino)pyridine-N,N')-dimethyl amino-dimethylamido-titanium (Fuhrmann et al., 1996). The S—O bond distances [1.471 (3), 1.477 (3) Å] reflect the equivalent dative binding of the O atoms to the titanium centres (Lensink et al., 2001). By comparison with the free 3-[3-indenyl]propyl group in N-(3-(3-indenyl)propyl)benzylammonium bromide (Groux et al., 1995), it appears that the total geometry of the group is unaffected by its link to the complex, with the only significant difference being close to the nitrogen N1, with an N1—C8—C9—C10 torsion angle here of 74.8 (5)° compared with −54.4 (3)°.

Experimental top

A solution of C₉H₇(CH₂)₃N(H)SO₂C₆H₄CH₃ (0.13 g, 0.40 mmol) in benzene-d6 (2 ml) was added dropwise to a solution of Ti(NMe₂)₄ (89 mg, 0.40 mmol) dissolved in benzene-d6 (3 ml), turning the mixture from yellow to orange. The mixture was refluxed over a period of 4 days. Subsequently Me₃SiCl (108 mg, 0.99 mmol) was slowly added. The mixture was stirred for 20 h, resulting in a dark-brown solution. Recrystallization from a CH₂Cl₂/pentane mixture resulted in crystals suitable for X-ray analysis. Yield: 20 mg (10%).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART (Siemens, 1996); data reduction: SAINT (Siemens, 1996) and SADABS (Sheldrick, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top

Fig. 1. Molecular structure of [Ti(C₂₁H₂₆N₂O₂S)Cl₂] (Farrugia, 1997). Displacement ellipsoids are drawn at the 30% probability level. H atoms have arbitrary radii.

(I) top

Crystal data top

[Ti(C₂₁H₂₆NO₂S)Cl₂]	Z = 2
M_r = 489.30	F(000) = 508
Triclinic, P1	D_x = 1.407 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.688 (3) Å	Cell parameters from 6100 reflections
b = 10.122 (5) Å	θ = 2.6–25.8°
c = 16.212 (7) Å	µ = 0.71 mm⁻¹
α = 94.808 (6)°	T = 170 K
β = 100.973 (5)°	Block, orange-brown
γ = 109.200 (5)°	0.36 × 0.20 × 0.16 mm
V = 1154.9 (9) Å³

Data collection top

Make? CCD area-detector diffractometer	4641 independent reflections
Radiation source: fine-focus sealed tube	2627 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.078
Detector resolution: 8.192 pixels mm^-1	θ_max = 26.4°, θ_min = 2.3°
ϕ and ω scans	h = −9→4
Absorption correction: multi-scan (Blessing, 1995)	k = −12→12
T_min = 0.393, T_max = 0.892	l = −20→20
14834 measured reflections

Refinement top

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H-atom parameters constrained
S = 0.94	w = 1/[σ²(F_o²) + (0.0747P)²] where P = (F_o² + 2F_c²)/3
4641 reflections	(Δ/σ)_max = 0.001
264 parameters	Δρ_max = 0.73 e Å⁻³
0 restraints	Δρ_min = −0.54 e Å⁻³

Crystal data top

[Ti(C₂₁H₂₆NO₂S)Cl₂]	γ = 109.200 (5)°
M_r = 489.30	V = 1154.9 (9) Å³
Triclinic, P1	Z = 2
a = 7.688 (3) Å	Mo Kα radiation
b = 10.122 (5) Å	µ = 0.71 mm⁻¹
c = 16.212 (7) Å	T = 170 K
α = 94.808 (6)°	0.36 × 0.20 × 0.16 mm
β = 100.973 (5)°

Data collection top

Make? CCD area-detector diffractometer	4641 independent reflections
Absorption correction: multi-scan (Blessing, 1995)	2627 reflections with I > 2σ(I)
T_min = 0.393, T_max = 0.892	R_int = 0.078
14834 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.140	H-atom parameters constrained
S = 0.94	Δρ_max = 0.73 e Å⁻³
4641 reflections	Δρ_min = −0.54 e Å⁻³
264 parameters

Special details top

Experimental. Crystal decay was monitored by repeating the initial 10 frames at the end of the data collection and analyzing duplicate reflections. The standard 1.0 mm diameter collimator was used.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Ti1	0.94332 (10)	0.28639 (7)	0.38452 (4)	0.0292 (2)
Cl1	0.95819 (16)	0.25997 (11)	0.24397 (6)	0.0419 (3)
Cl2	1.17818 (16)	0.19587 (12)	0.43266 (7)	0.0456 (3)
S1	1.02898 (14)	0.58169 (10)	0.40401 (6)	0.0286 (3)
O1	1.1662 (4)	0.5083 (3)	0.40947 (16)	0.0305 (6)
O2	0.9501 (4)	0.3195 (3)	0.51925 (16)	0.0347 (7)
N1	0.8382 (4)	0.4523 (3)	0.37891 (19)	0.0299 (8)
N2	0.7201 (5)	0.1317 (4)	0.3684 (2)	0.0420 (9)
C1	1.0635 (5)	0.6921 (4)	0.3245 (2)	0.0273 (9)
C2	1.1104 (6)	0.6447 (4)	0.2518 (2)	0.0336 (10)
H2	1.1305	0.5569	0.2462	0.040*
C3	1.1275 (6)	0.7269 (4)	0.1875 (3)	0.0359 (10)
H3	1.1596	0.6945	0.1378	0.043*
C4	1.0986 (5)	0.8563 (4)	0.1941 (3)	0.0347 (10)
C5	1.0513 (6)	0.9014 (4)	0.2677 (3)	0.0388 (11)
H5	1.0303	0.9888	0.2733	0.047*
C6	1.0344 (6)	0.8202 (4)	0.3331 (2)	0.0344 (10)
H6	1.0031	0.8524	0.3831	0.041*
C7	1.1197 (7)	0.9453 (5)	0.1235 (3)	0.0502 (13)
H7A	1.1529	0.8967	0.0773	0.060*
H7B	1.2199	1.0376	0.1457	0.060*
H7C	1.0000	0.9591	0.1017	0.060*
C8	0.6535 (6)	0.4668 (5)	0.3838 (3)	0.0403 (11)
H8A	0.6771	0.5638	0.4120	0.048*
H8B	0.5920	0.3994	0.4194	0.048*
C9	0.5186 (6)	0.4390 (5)	0.2963 (3)	0.0453 (12)
H9A	0.5168	0.3511	0.2638	0.054*
H9B	0.3891	0.4224	0.3045	0.054*
C10	0.5674 (7)	0.5560 (5)	0.2441 (3)	0.0502 (13)
H10A	0.6985	0.5750	0.2376	0.060*
H10B	0.5648	0.6431	0.2757	0.060*
C11	0.4381 (6)	0.5267 (5)	0.1564 (3)	0.0411 (11)
C12	0.2972 (6)	0.4079 (5)	0.1174 (3)	0.0423 (11)
H12	0.2561	0.3252	0.1427	0.051*
C13	0.2098 (6)	0.4207 (5)	0.0272 (3)	0.0454 (12)
H13A	0.2244	0.3515	−0.0154	0.054*
H13B	0.0739	0.4069	0.0199	0.054*
C14	0.3240 (6)	0.5704 (5)	0.0205 (3)	0.0416 (11)
C15	0.4566 (6)	0.6325 (5)	0.0976 (3)	0.0397 (11)
C16	0.5788 (7)	0.7745 (5)	0.1090 (3)	0.0539 (13)
H16	0.6688	0.8182	0.1612	0.065*
C17	0.5625 (8)	0.8490 (6)	0.0404 (4)	0.0618 (15)
H17	0.6428	0.9450	0.0461	0.074*
C18	0.4307 (8)	0.7844 (7)	−0.0357 (4)	0.0680 (16)
H18	0.4244	0.8363	−0.0816	0.082*
C19	0.3092 (7)	0.6469 (6)	−0.0457 (3)	0.0555 (14)
H19	0.2164	0.6050	−0.0972	0.067*
C20A	0.6843 (11)	0.0315 (9)	0.4275 (5)	0.069 (2)*	0.785 (11)
H20A	0.5903	0.0454	0.4571	0.083*	0.785 (11)
H20B	0.8023	0.0465	0.4691	0.083*	0.785 (11)
H20C	0.6361	−0.0653	0.3962	0.083*	0.785 (11)
C20B	0.612 (4)	0.092 (3)	0.4359 (17)	0.069 (2)*	0.215 (11)
H20D	0.5607	0.1657	0.4502	0.083*	0.215 (11)
H20E	0.6962	0.0830	0.4868	0.083*	0.215 (11)
H20F	0.5072	0.0015	0.4147	0.083*	0.215 (11)
C21	0.5616 (8)	0.0853 (6)	0.2922 (3)	0.0774 (18)
H21A	0.5378	−0.0132	0.2688	0.093*
H21B	0.5943	0.1460	0.2493	0.093*
H21C	0.4475	0.0922	0.3078	0.093*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ti1	0.0380 (4)	0.0287 (4)	0.0230 (4)	0.0135 (3)	0.0078 (3)	0.0065 (3)
Cl1	0.0590 (7)	0.0422 (7)	0.0272 (6)	0.0186 (6)	0.0149 (5)	0.0062 (5)
Cl2	0.0586 (7)	0.0432 (7)	0.0424 (7)	0.0318 (6)	0.0050 (5)	0.0057 (5)
S1	0.0387 (6)	0.0300 (5)	0.0220 (5)	0.0166 (5)	0.0088 (4)	0.0085 (4)
O1	0.0380 (16)	0.0301 (15)	0.0287 (15)	0.0188 (13)	0.0071 (12)	0.0075 (12)
O2	0.0565 (18)	0.0312 (16)	0.0216 (14)	0.0199 (14)	0.0125 (13)	0.0060 (12)
N1	0.0385 (19)	0.0332 (19)	0.0256 (18)	0.0181 (16)	0.0134 (15)	0.0097 (15)
N2	0.043 (2)	0.043 (2)	0.038 (2)	0.0087 (18)	0.0145 (17)	0.0120 (17)
C1	0.034 (2)	0.032 (2)	0.022 (2)	0.0150 (19)	0.0093 (17)	0.0110 (17)
C2	0.043 (2)	0.032 (2)	0.033 (2)	0.019 (2)	0.0133 (19)	0.0092 (19)
C3	0.038 (2)	0.047 (3)	0.026 (2)	0.016 (2)	0.0125 (18)	0.009 (2)
C4	0.034 (2)	0.037 (2)	0.034 (2)	0.011 (2)	0.0099 (19)	0.0121 (19)
C5	0.054 (3)	0.028 (2)	0.035 (3)	0.016 (2)	0.008 (2)	0.0090 (19)
C6	0.049 (3)	0.032 (2)	0.026 (2)	0.019 (2)	0.0091 (19)	0.0040 (18)
C7	0.070 (3)	0.041 (3)	0.038 (3)	0.013 (3)	0.017 (2)	0.015 (2)
C8	0.039 (2)	0.051 (3)	0.041 (3)	0.024 (2)	0.012 (2)	0.015 (2)
C9	0.045 (3)	0.050 (3)	0.045 (3)	0.021 (2)	0.007 (2)	0.015 (2)
C10	0.052 (3)	0.058 (3)	0.044 (3)	0.025 (3)	0.006 (2)	0.016 (2)
C11	0.044 (3)	0.050 (3)	0.037 (3)	0.025 (2)	0.012 (2)	0.010 (2)
C12	0.044 (3)	0.051 (3)	0.044 (3)	0.025 (2)	0.020 (2)	0.017 (2)
C13	0.042 (3)	0.059 (3)	0.037 (3)	0.023 (2)	0.009 (2)	−0.001 (2)
C14	0.046 (3)	0.064 (3)	0.033 (2)	0.038 (3)	0.020 (2)	0.013 (2)
C15	0.038 (2)	0.048 (3)	0.044 (3)	0.025 (2)	0.015 (2)	0.016 (2)
C16	0.052 (3)	0.063 (3)	0.053 (3)	0.029 (3)	0.009 (2)	0.011 (3)
C17	0.072 (4)	0.052 (3)	0.079 (4)	0.032 (3)	0.030 (3)	0.032 (3)
C18	0.087 (4)	0.092 (5)	0.058 (4)	0.062 (4)	0.029 (3)	0.034 (3)
C19	0.065 (3)	0.075 (4)	0.043 (3)	0.040 (3)	0.019 (3)	0.021 (3)
C21	0.064 (4)	0.070 (4)	0.069 (4)	−0.003 (3)	0.001 (3)	−0.001 (3)

Geometric parameters (Å, º) top

Ti1—N2	1.860 (4)	C9—C10	1.502 (6)
Ti1—N1	2.091 (3)	C9—H9A	0.9900
Ti1—O2	2.170 (3)	C9—H9B	0.9900
Ti1—O1	2.280 (3)	C10—C11	1.515 (6)
Ti1—Cl1	2.3010 (16)	C10—H10A	0.9900
Ti1—Cl2	2.3196 (14)	C10—H10B	0.9900
S1—O1	1.471 (3)	C11—C12	1.331 (6)
S1—O2ⁱ	1.477 (3)	C11—C15	1.482 (6)
S1—N1	1.566 (3)	C12—C13	1.523 (6)
S1—C1	1.776 (4)	C12—H12	0.9500
O2—S1ⁱ	1.477 (3)	C13—C14	1.506 (6)
N1—C8	1.491 (5)	C13—H13A	0.9900
N2—C20A	1.450 (7)	C13—H13B	0.9900
N2—C21	1.479 (6)	C14—C19	1.383 (6)
N2—C20B	1.50 (3)	C14—C15	1.400 (6)
C1—C6	1.387 (5)	C15—C16	1.408 (6)
C1—C2	1.389 (5)	C16—C17	1.404 (6)
C2—C3	1.387 (5)	C16—H16	0.9500
C2—H2	0.9500	C17—C18	1.389 (7)
C3—C4	1.397 (6)	C17—H17	0.9500
C3—H3	0.9500	C18—C19	1.373 (7)
C4—C5	1.395 (6)	C18—H18	0.9500
C4—C7	1.516 (5)	C19—H19	0.9500
C5—C6	1.395 (5)	C20A—H20A	0.9800
C5—H5	0.9500	C20A—H20B	0.9800
C6—H6	0.9500	C20A—H20C	0.9800
C7—H7A	0.9800	C20B—H20D	0.9800
C7—H7B	0.9800	C20B—H20E	0.9800
C7—H7C	0.9800	C20B—H20F	0.9800
C8—C9	1.533 (6)	C21—H21A	0.9800
C8—H8A	0.9900	C21—H21B	0.9800
C8—H8B	0.9900	C21—H21C	0.9800

N2—Ti1—N1	100.84 (15)	C9—C8—H8B	109.0
N2—Ti1—O2	89.40 (13)	H8A—C8—H8B	107.8
N1—Ti1—O2	84.76 (11)	C10—C9—C8	115.0 (4)
N2—Ti1—O1	164.90 (14)	C10—C9—H9A	108.5
N1—Ti1—O1	64.48 (12)	C8—C9—H9A	108.5
O2—Ti1—O1	85.83 (10)	C10—C9—H9B	108.5
N2—Ti1—Cl1	94.28 (12)	C8—C9—H9B	108.5
N1—Ti1—Cl1	95.94 (9)	H9A—C9—H9B	107.5
O2—Ti1—Cl1	176.05 (8)	C9—C10—C11	115.1 (4)
O1—Ti1—Cl1	90.96 (7)	C9—C10—H10A	108.5
N2—Ti1—Cl2	103.80 (12)	C11—C10—H10A	108.5
N1—Ti1—Cl2	151.82 (10)	C9—C10—H10B	108.5
O2—Ti1—Cl2	82.06 (8)	C11—C10—H10B	108.5
O1—Ti1—Cl2	89.73 (8)	H10A—C10—H10B	107.5
Cl1—Ti1—Cl2	95.64 (5)	C12—C11—C15	108.3 (4)
O1—S1—O2ⁱ	116.01 (16)	C12—C11—C10	128.7 (4)
O1—S1—N1	100.58 (17)	C15—C11—C10	122.9 (4)
O2ⁱ—S1—N1	114.78 (17)	C11—C12—C13	111.9 (4)
O1—S1—C1	108.32 (17)	C11—C12—H12	124.1
O2ⁱ—S1—C1	103.70 (18)	C13—C12—H12	124.1
N1—S1—C1	113.70 (17)	C14—C13—C12	102.1 (3)
S1—O1—Ti1	94.92 (13)	C14—C13—H13A	111.4
S1ⁱ—O2—Ti1	148.35 (16)	C12—C13—H13A	111.4
C8—N1—S1	122.1 (3)	C14—C13—H13B	111.4
C8—N1—Ti1	134.6 (3)	C12—C13—H13B	111.4
S1—N1—Ti1	99.79 (16)	H13A—C13—H13B	109.2
C20A—N2—C21	109.9 (4)	C19—C14—C15	120.9 (5)
C21—N2—C20B	99.8 (11)	C19—C14—C13	130.2 (4)
C20A—N2—Ti1	123.8 (4)	C15—C14—C13	108.8 (4)
C21—N2—Ti1	126.1 (3)	C14—C15—C16	120.4 (4)
C20B—N2—Ti1	124.2 (11)	C14—C15—C11	108.9 (4)
C6—C1—C2	120.6 (4)	C16—C15—C11	130.7 (4)
C6—C1—S1	120.4 (3)	C17—C16—C15	117.5 (5)
C2—C1—S1	118.9 (3)	C17—C16—H16	121.3
C3—C2—C1	119.2 (4)	C15—C16—H16	121.3
C3—C2—H2	120.4	C18—C17—C16	120.9 (5)
C1—C2—H2	120.4	C18—C17—H17	119.5
C2—C3—C4	121.5 (4)	C16—C17—H17	119.5
C2—C3—H3	119.2	C19—C18—C17	121.3 (5)
C4—C3—H3	119.2	C19—C18—H18	119.4
C5—C4—C3	118.1 (4)	C17—C18—H18	119.4
C5—C4—C7	121.1 (4)	C18—C19—C14	119.0 (5)
C3—C4—C7	120.7 (4)	C18—C19—H19	120.5
C6—C5—C4	121.0 (4)	C14—C19—H19	120.5
C6—C5—H5	119.5	N2—C20A—H20A	109.5
C4—C5—H5	119.5	N2—C20A—H20B	109.5
C1—C6—C5	119.5 (4)	N2—C20A—H20C	109.5
C1—C6—H6	120.3	N2—C20B—H20D	109.5
C5—C6—H6	120.3	N2—C20B—H20E	109.5
C4—C7—H7A	109.5	H20D—C20B—H20E	109.5
C4—C7—H7B	109.5	N2—C20B—H20F	109.5
H7A—C7—H7B	109.5	H20D—C20B—H20F	109.5
C4—C7—H7C	109.5	H20E—C20B—H20F	109.5
H7A—C7—H7C	109.5	N2—C21—H21A	109.5
H7B—C7—H7C	109.5	N2—C21—H21B	109.5
N1—C8—C9	112.9 (4)	H21A—C21—H21B	109.5
N1—C8—H8A	109.0	N2—C21—H21C	109.5
C9—C8—H8A	109.0	H21A—C21—H21C	109.5
N1—C8—H8B	109.0	H21B—C21—H21C	109.5

O2ⁱ—S1—O1—Ti1	120.47 (14)	O1—S1—C1—C6	−146.5 (3)
N1—S1—O1—Ti1	−3.98 (15)	O2ⁱ—S1—C1—C6	−22.7 (4)
C1—S1—O1—Ti1	−123.49 (15)	N1—S1—C1—C6	102.6 (3)
N2—Ti1—O1—S1	−11.0 (5)	Ti1—S1—C1—C6	155.6 (3)
N1—Ti1—O1—S1	3.24 (12)	O1—S1—C1—C2	36.9 (3)
O2—Ti1—O1—S1	−82.93 (13)	O2ⁱ—S1—C1—C2	160.7 (3)
Cl1—Ti1—O1—S1	99.37 (11)	N1—S1—C1—C2	−74.0 (3)
Cl2—Ti1—O1—S1	−164.99 (11)	Ti1—S1—C1—C2	−21.0 (4)
N2—Ti1—O2—S1ⁱ	−130.9 (3)	C6—C1—C2—C3	−0.1 (6)
N1—Ti1—O2—S1ⁱ	−29.9 (3)	S1—C1—C2—C3	176.5 (3)
O1—Ti1—O2—S1ⁱ	34.8 (3)	C1—C2—C3—C4	0.0 (6)
Cl2—Ti1—O2—S1ⁱ	125.1 (3)	C2—C3—C4—C5	−0.1 (6)
O1—S1—N1—C8	166.1 (3)	C2—C3—C4—C7	179.5 (4)
O2ⁱ—S1—N1—C8	40.9 (3)	C3—C4—C5—C6	0.4 (6)
C1—S1—N1—C8	−78.3 (3)	C7—C4—C5—C6	−179.2 (4)
Ti1—S1—N1—C8	161.8 (4)	C2—C1—C6—C5	0.4 (6)
O1—S1—N1—Ti1	4.39 (17)	S1—C1—C6—C5	−176.2 (3)
O2ⁱ—S1—N1—Ti1	−120.90 (15)	C4—C5—C6—C1	−0.5 (6)
C1—S1—N1—Ti1	119.93 (17)	S1—N1—C8—C9	113.5 (4)
N2—Ti1—N1—C8	15.0 (4)	Ti1—N1—C8—C9	−92.2 (4)
O2—Ti1—N1—C8	−73.4 (3)	N1—C8—C9—C10	−74.8 (5)
O1—Ti1—N1—C8	−161.2 (4)	C8—C9—C10—C11	178.0 (4)
Cl1—Ti1—N1—C8	110.5 (3)	C9—C10—C11—C12	−5.7 (7)
Cl2—Ti1—N1—C8	−135.7 (3)	C9—C10—C11—C15	176.2 (4)
N2—Ti1—N1—S1	173.17 (16)	C15—C11—C12—C13	1.5 (5)
O2—Ti1—N1—S1	84.79 (15)	C10—C11—C12—C13	−176.8 (4)
O1—Ti1—N1—S1	−3.08 (12)	C11—C12—C13—C14	−0.8 (5)
Cl1—Ti1—N1—S1	−91.30 (13)	C12—C13—C14—C19	−178.1 (5)
Cl2—Ti1—N1—S1	22.5 (3)	C12—C13—C14—C15	−0.4 (5)
N1—Ti1—N2—C20A	−123.6 (5)	C19—C14—C15—C16	−0.4 (7)
O2—Ti1—N2—C20A	−39.1 (5)	C13—C14—C15—C16	−178.4 (4)
O1—Ti1—N2—C20A	−110.5 (7)	C19—C14—C15—C11	179.2 (4)
Cl1—Ti1—N2—C20A	139.5 (5)	C13—C14—C15—C11	1.3 (5)
Cl2—Ti1—N2—C20A	42.6 (5)	C12—C11—C15—C14	−1.8 (5)
N1—Ti1—N2—C21	61.9 (4)	C10—C11—C15—C14	176.6 (4)
O2—Ti1—N2—C21	146.4 (4)	C12—C11—C15—C16	177.8 (5)
O1—Ti1—N2—C21	75.0 (7)	C10—C11—C15—C16	−3.8 (8)
Cl1—Ti1—N2—C21	−35.0 (4)	C14—C15—C16—C17	−0.5 (7)
Cl2—Ti1—N2—C21	−131.9 (4)	C11—C15—C16—C17	180.0 (5)
N1—Ti1—N2—C20B	−76.8 (16)	C15—C16—C17—C18	−0.1 (8)
O2—Ti1—N2—C20B	7.7 (16)	C16—C17—C18—C19	1.5 (8)
O1—Ti1—N2—C20B	−63.7 (16)	C17—C18—C19—C14	−2.4 (8)
Cl1—Ti1—N2—C20B	−173.7 (16)	C15—C14—C19—C18	1.9 (7)
Cl2—Ti1—N2—C20B	89.4 (16)	C13—C14—C19—C18	179.3 (4)

Symmetry code: (i) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Ti(C₂₁H₂₆NO₂S)Cl₂]
M_r	489.30
Crystal system, space group	Triclinic, P1
Temperature (K)	170
a, b, c (Å)	7.688 (3), 10.122 (5), 16.212 (7)
α, β, γ (°)	94.808 (6), 100.973 (5), 109.200 (5)
V (Å³)	1154.9 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.71
Crystal size (mm)	0.36 × 0.20 × 0.16

Data collection
Diffractometer	Make? CCD area-detector diffractometer
Absorption correction	Multi-scan (Blessing, 1995)
T_min, T_max	0.393, 0.892
No. of measured, independent and observed [I > 2σ(I)] reflections	14834, 4641, 2627
R_int	0.078
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.140, 0.94
No. of reflections	4641
No. of parameters	264
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.73, −0.54

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996) and SADABS (Sheldrick, 1996), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXL97.

Selected geometric parameters (Å, º) top

Ti1—N2	1.860 (4)	Ti1—Cl2	2.3196 (14)
Ti1—N1	2.091 (3)	S1—O1	1.471 (3)
Ti1—O2	2.170 (3)	S1—O2ⁱ	1.477 (3)
Ti1—O1	2.280 (3)	S1—N1	1.566 (3)
Ti1—Cl1	2.3010 (16)	S1—C1	1.776 (4)

N2—Ti1—N1	100.84 (15)	C8—N1—Ti1	134.6 (3)
Cl1—Ti1—Cl2	95.64 (5)	S1—N1—Ti1	99.79 (16)
C8—N1—S1	122.1 (3)

Symmetry code: (i) −x+2, −y+1, −z+1.

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