Dichloro­[(3-methyl-2-p-tolyl­sulfon­amido­butyl)-κ²N,O:η⁵-cyclo­penta­dienyl]­titanium

The title compound, [TiCl₂(C₁₇H₂₁NO₂S)], has a five-coordinate Ti atom bonded to the N and one O atom of the sulfon­amide, which is tethered by a substituted two-carbon chain to a bound cyclo­penta­diene, the cyclo­penta­diene and two Cl atoms. The Ti—N/O(sulfon­amide) bond lengths are 2.0095 (19) and 2.2819 (13) Å, respectively, with the Ti—O bond through one face of the approximate tetrahedron formed by the other four bonds about the titanium.

Key indicators

• Single-crystal X-ray study
• T = 163 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.021
• wR factor = 0.056
• Data-to-parameter ratio = 17.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

General Notes



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           26.50
         From the CIF: _reflns_number_total               3902
         Count of symmetry unique reflns         2271
         Completeness (_total/calc)            171.82%
         TEST3: Check Friedels for noncentro structure
         Estimate of Friedel pairs measured      1631
         Fraction of Friedel pairs measured     0.718
         Are heavy atom types Z>Si present          yes
          Please check that the estimate of the number of Friedel pairs is
          correct. If it is not, please give the correct count in the
          _publ_section_exptl_refinement section of the submitted CIF.

---

S1. Comment

The title compound, (I), is related to previously reported structures (Lensink et al., 2001; Lensink, 1998). The crystal structure consists of independent molecules of the absolute configuration shown (Fig. 1) with only one weak intermolecular contact C13—H13····O1(x - 1/2, -3/2 - y, -2 - z) of 2.48 Å. The Ti atom has fivefold coordination through the N and one O atom of the sulfonamide, a cyclopentadiene (assumed to occupy one coordination site) linked via an ethyl linkage to the nitrogen, and two Cl atoms. The S—O bonds [O1: 1.431 (1); O2: 1.471 (1) Å] confirm the significant bonding of atom O2 to the titanium in comparison with the free ligand (Gainsford & Lensink, 1996). The Ti—C_g distance is 2.04 Å, within the narrow range 2.01–2.08 Å observed previously (Lensink et al., 2001; Allen & Kennard, 1993; Cambridge Structural Database, 2000). The Ti coordination geometry can best be described as based on a tetrahedron formed by the cyclopentadiene, Cl1, Cl2 and N1, with the Ti—O2 bond through the face formed by N1, Cl1 and Cl2; the angles subtended by O2 at the Ti atom to these three atoms are 65.33 (5), 83.39 (4) and 77.39 (4)°, respectively.

S2. Experimental

The title compound was prepared from the stoichiometric reaction of Ti(NMe₂)₄ with N-(3-methyl-2-p-tolylsulfonamidobutyl)cyclopentadiene followed by treatment with excess Me₃SiCl. Crystals were obtained from dichloromethane/pentane. Details and spectroscopic data will be reported in a future publication.

S3. Refinement

All H atoms, except those on methyl C atoms, were constrained to an isotropic displacement parameter 1.2 times that of the equivalent U of their parent atom. The factor was 1.5 times for the methyl H atoms.

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SMART; 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 in WinGX (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures

Fig. 1. The molecular structure of (I) (Farrugia, 1997). Displacement ellipsoids are drawn at the 30% probability level. H atoms (unlabelled) have arbitrary radii.

Dichoro[(3-methyl-2-p-tolylsulfonamidobutyl)-κ²N,O:η⁵-cyclopentadienyl]- titanium

Crystal data

[TiCl2(C17H21NO2S)]	Dx = 1.466 Mg m^−3
Mr = 422.21	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 8192 reflections
a = 8.8053 (18) Å	θ = 2.7–26.4°
b = 13.885 (3) Å	µ = 0.85 mm^−1
c = 15.647 (3) Å	T = 163 K
V = 1913.0 (7) Å^3	Block, yellow
Z = 4	0.60 × 0.54 × 0.53 mm
F(000) = 872

Data collection

CCD area-detector diffractometer	3902 independent reflections
Radiation source: fine-focus sealed tube	3769 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
Detector resolution: 8.192 pixels mm^-1	θmax = 26.5°, θmin = 2.7°
ϕ and ω scans	h = −11→10
Absorption correction: multi scan (Blessing, 1995)	k = −17→17
Tmin = 0.571, Tmax = 0.639	l = −7→19
10578 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.021	H-atom parameters constrained
wR(F^2) = 0.056	w = 1/[σ^2(Fo^2) + (0.0315P)^2 + 0.3134P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.032
3902 reflections	Δρmax = 0.20 e Å^−3
220 parameters	Δρmin = −0.17 e Å^−3
0 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (2)

Special details

Experimental. Crystal decay was monitored by repeating the initial 10 frames at the end of the data collection and analyzing duplicate reflections. The standard 0.8 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 (Ų)

	x	y	z	Uiso*/Ueq
Ti1	−0.06464 (4)	−0.75884 (2)	−0.857962 (18)	0.02795 (8)
S1	0.19418 (5)	−0.68270 (3)	−0.77800 (2)	0.02726 (9)
Cl2	−0.08012 (6)	−0.64725 (3)	−0.96755 (3)	0.04066 (11)
Cl1	−0.24725 (6)	−0.72021 (4)	−0.75960 (3)	0.04341 (12)
O1	0.33386 (16)	−0.65957 (9)	−0.82000 (8)	0.0377 (3)
O2	0.05716 (17)	−0.62834 (8)	−0.80174 (8)	0.0359 (3)
N1	0.13216 (16)	−0.78905 (10)	−0.79873 (9)	0.0273 (3)
C1	0.2225 (2)	−0.66440 (11)	−0.66797 (10)	0.0280 (4)
C2	0.3684 (2)	−0.64777 (12)	−0.63846 (11)	0.0323 (4)
H2	0.4529	−0.6518	−0.6760	0.039*
C3	0.3885 (2)	−0.62506 (14)	−0.55252 (12)	0.0394 (4)
H3	0.4881	−0.6133	−0.5316	0.047*
C4	0.2675 (3)	−0.61925 (14)	−0.49740 (11)	0.0410 (5)
C5	0.1213 (2)	−0.63977 (14)	−0.52810 (12)	0.0394 (4)
H5	0.0375	−0.6386	−0.4899	0.047*
C6	0.0974 (2)	−0.66184 (12)	−0.61389 (11)	0.0331 (4)
H6	−0.0017	−0.6748	−0.6349	0.040*
C7	0.2902 (3)	−0.58909 (19)	−0.40564 (13)	0.0581 (6)
H7A	0.3925	−0.6072	−0.3870	0.087*
H7B	0.2149	−0.6213	−0.3695	0.087*
H7C	0.2779	−0.5192	−0.4008	0.087*
C8	0.2392 (2)	−0.87172 (12)	−0.80426 (12)	0.0343 (4)
H8	0.3125	−0.8587	−0.8517	0.041*
C9	0.1378 (3)	−0.95795 (14)	−0.83067 (18)	0.0537 (6)
H9A	0.1957	−1.0013	−0.8689	0.064*
H9B	0.1083	−0.9949	−0.7792	0.064*
C10	−0.0009 (2)	−0.92340 (13)	−0.87543 (12)	0.0376 (4)
C11	−0.1479 (2)	−0.91827 (14)	−0.83980 (12)	0.0379 (4)
H11	−0.1761	−0.9399	−0.7844	0.045*
C12	−0.2450 (3)	−0.87588 (15)	−0.89988 (13)	0.0449 (5)
H12	−0.3504	−0.8641	−0.8924	0.054*
C13	−0.1610 (3)	−0.85419 (15)	−0.97200 (13)	0.0484 (5)
H13	−0.1994	−0.8259	−1.0229	0.058*
C14	−0.0095 (3)	−0.88093 (14)	−0.95742 (13)	0.0438 (5)
H14	0.0728	−0.8721	−0.9959	0.053*
C15	0.3299 (2)	−0.89083 (13)	−0.72281 (15)	0.0411 (4)
H15	0.3921	−0.8321	−0.7107	0.049*
C16	0.4398 (3)	−0.97457 (16)	−0.7382 (2)	0.0724 (9)
H16A	0.5017	−0.9849	−0.6870	0.109*
H16B	0.5060	−0.9593	−0.7867	0.109*
H16C	0.3819	−1.0332	−0.7508	0.109*
C17	0.2335 (3)	−0.91055 (16)	−0.64506 (16)	0.0549 (6)
H17A	0.1586	−0.8589	−0.6383	0.082*
H17B	0.2983	−0.9133	−0.5942	0.082*
H17C	0.1808	−0.9722	−0.6522	0.082*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ti1	0.03233 (15)	0.02809 (15)	0.02343 (13)	−0.00239 (13)	−0.00169 (12)	0.00180 (11)
S1	0.0376 (2)	0.02122 (18)	0.02294 (17)	−0.00409 (17)	−0.00184 (17)	−0.00013 (15)
Cl2	0.0467 (3)	0.0435 (2)	0.0318 (2)	−0.0046 (2)	−0.0083 (2)	0.01186 (18)
Cl1	0.0435 (2)	0.0426 (3)	0.0441 (3)	0.0050 (2)	0.0103 (2)	0.00163 (19)
O1	0.0472 (8)	0.0388 (7)	0.0272 (6)	−0.0157 (6)	0.0026 (5)	0.0001 (5)
O2	0.0510 (8)	0.0238 (6)	0.0329 (6)	0.0030 (6)	−0.0115 (6)	0.0013 (5)
N1	0.0319 (7)	0.0216 (7)	0.0284 (7)	−0.0009 (6)	−0.0010 (6)	−0.0022 (5)
C1	0.0414 (10)	0.0197 (7)	0.0228 (7)	0.0003 (7)	−0.0010 (7)	−0.0002 (6)
C2	0.0383 (9)	0.0304 (9)	0.0281 (8)	−0.0021 (7)	−0.0015 (8)	0.0002 (7)
C3	0.0467 (11)	0.0403 (10)	0.0313 (9)	−0.0046 (8)	−0.0083 (8)	−0.0023 (8)
C4	0.0605 (13)	0.0358 (10)	0.0266 (9)	0.0044 (9)	−0.0036 (8)	−0.0012 (7)
C5	0.0513 (11)	0.0371 (10)	0.0299 (9)	0.0052 (9)	0.0070 (8)	−0.0006 (8)
C6	0.0385 (10)	0.0287 (8)	0.0321 (8)	0.0025 (7)	0.0000 (7)	0.0002 (7)
C7	0.0762 (17)	0.0695 (15)	0.0285 (10)	0.0000 (13)	−0.0057 (10)	−0.0079 (9)
C8	0.0330 (9)	0.0245 (8)	0.0454 (10)	0.0010 (7)	0.0066 (8)	−0.0079 (7)
C9	0.0576 (13)	0.0261 (10)	0.0774 (16)	0.0029 (9)	−0.0176 (12)	−0.0142 (10)
C10	0.0483 (11)	0.0250 (9)	0.0396 (10)	−0.0049 (8)	−0.0041 (8)	−0.0100 (8)
C11	0.0484 (11)	0.0325 (9)	0.0328 (9)	−0.0146 (9)	0.0000 (8)	−0.0009 (7)
C12	0.0420 (11)	0.0462 (11)	0.0466 (11)	−0.0142 (9)	−0.0069 (9)	−0.0037 (9)
C13	0.0676 (15)	0.0463 (12)	0.0314 (9)	−0.0164 (11)	−0.0126 (10)	−0.0034 (8)
C14	0.0583 (12)	0.0381 (11)	0.0351 (10)	−0.0149 (9)	0.0105 (9)	−0.0121 (8)
C15	0.0273 (9)	0.0254 (9)	0.0707 (13)	0.0001 (7)	−0.0091 (9)	−0.0004 (9)
C16	0.0351 (11)	0.0313 (11)	0.151 (3)	0.0064 (10)	−0.0098 (16)	−0.0045 (14)
C17	0.0683 (15)	0.0418 (11)	0.0547 (13)	0.0031 (11)	−0.0096 (12)	0.0127 (10)

Geometric parameters (Å, º)

Ti1—N1	2.0095 (15)	C7—H7B	0.9800
Ti1—O2	2.2819 (13)	C7—H7C	0.9800
Ti1—Cl1	2.2895 (6)	C8—C15	1.527 (3)
Ti1—Cl2	2.3150 (6)	C8—C9	1.549 (3)
Ti1—C11	2.3491 (19)	C8—H8	1.0000
Ti1—C14	2.3520 (19)	C9—C10	1.488 (3)
Ti1—C12	2.365 (2)	C9—H9A	0.9900
Ti1—C10	2.3686 (19)	C9—H9B	0.9900
Ti1—C13	2.3784 (19)	C10—C11	1.411 (3)
S1—O1	1.4309 (14)	C10—C14	1.414 (3)
S1—O2	1.4709 (14)	C11—C12	1.401 (3)
S1—N1	1.6075 (14)	C11—H11	0.9500
S1—C1	1.7582 (16)	C12—C13	1.383 (3)
N1—C8	1.488 (2)	C12—H12	0.9500
C1—C2	1.385 (3)	C13—C14	1.404 (3)
C1—C6	1.389 (3)	C13—H13	0.9500
C2—C3	1.393 (3)	C14—H14	0.9500
C2—H2	0.9500	C15—C17	1.509 (3)
C3—C4	1.374 (3)	C15—C16	1.532 (3)
C3—H3	0.9500	C15—H15	1.0000
C4—C5	1.403 (3)	C16—H16A	0.9800
C4—C7	1.509 (3)	C16—H16B	0.9800
C5—C6	1.393 (3)	C16—H16C	0.9800
C5—H5	0.9500	C17—H17A	0.9800
C6—H6	0.9500	C17—H17B	0.9800
C7—H7A	0.9800	C17—H17C	0.9800
N1—Ti1—O2	65.33 (5)	C4—C7—H7B	109.5
N1—Ti1—Cl1	110.15 (4)	H7A—C7—H7B	109.5
O2—Ti1—Cl1	83.39 (4)	C4—C7—H7C	109.5
N1—Ti1—Cl2	122.15 (4)	H7A—C7—H7C	109.5
O2—Ti1—Cl2	77.39 (4)	H7B—C7—H7C	109.5
Cl1—Ti1—Cl2	107.44 (2)	N1—C8—C15	114.63 (14)
N1—Ti1—C11	90.95 (6)	N1—C8—C9	104.30 (15)
O2—Ti1—C11	148.02 (6)	C15—C8—C9	112.92 (16)
Cl1—Ti1—C11	85.43 (5)	N1—C8—H8	108.2
Cl2—Ti1—C11	134.58 (5)	C15—C8—H8	108.2
N1—Ti1—C14	88.66 (7)	C9—C8—H8	108.2
O2—Ti1—C14	136.91 (7)	C10—C9—C8	110.44 (16)
Cl1—Ti1—C14	139.35 (6)	C10—C9—H9A	109.6
Cl2—Ti1—C14	90.26 (6)	C8—C9—H9A	109.6
C11—Ti1—C14	57.67 (7)	C10—C9—H9B	109.6
N1—Ti1—C12	124.30 (7)	C8—C9—H9B	109.6
O2—Ti1—C12	165.49 (7)	H9A—C9—H9B	108.1
Cl1—Ti1—C12	82.86 (6)	C11—C10—C14	106.77 (18)
Cl2—Ti1—C12	102.41 (6)	C11—C10—C9	125.69 (19)
C11—Ti1—C12	34.57 (7)	C14—C10—C9	127.3 (2)
C14—Ti1—C12	57.31 (8)	C11—C10—Ti1	71.84 (11)
N1—Ti1—C10	69.36 (6)	C14—C10—Ti1	71.93 (11)
O2—Ti1—C10	134.35 (6)	C9—C10—Ti1	116.83 (12)
Cl1—Ti1—C10	118.03 (5)	C12—C11—C10	108.43 (17)
Cl2—Ti1—C10	125.04 (5)	C12—C11—Ti1	73.34 (11)
C11—Ti1—C10	34.80 (7)	C10—C11—Ti1	73.36 (11)
C14—Ti1—C10	34.86 (7)	C12—C11—H11	125.8
C12—Ti1—C10	57.61 (7)	C10—C11—H11	125.8
N1—Ti1—C13	122.51 (7)	Ti1—C11—H11	119.3
O2—Ti1—C13	154.01 (6)	C13—C12—C11	108.2 (2)
Cl1—Ti1—C13	112.59 (6)	C13—C12—Ti1	73.58 (11)
Cl2—Ti1—C13	78.22 (6)	C11—C12—Ti1	72.09 (11)
C11—Ti1—C13	56.97 (7)	C13—C12—H12	125.9
C14—Ti1—C13	34.52 (8)	C11—C12—H12	125.9
C12—Ti1—C13	33.89 (8)	Ti1—C12—H12	120.2
C10—Ti1—C13	57.39 (7)	C12—C13—C14	108.56 (19)
O1—S1—O2	118.29 (8)	C12—C13—Ti1	72.53 (11)
O1—S1—N1	113.93 (8)	C14—C13—Ti1	71.71 (11)
O2—S1—N1	98.15 (8)	C12—C13—H13	125.7
O1—S1—C1	107.19 (8)	C14—C13—H13	125.7
O2—S1—C1	106.82 (8)	Ti1—C13—H13	121.7
N1—S1—C1	112.24 (8)	C13—C14—C10	107.97 (19)
S1—O2—Ti1	94.33 (6)	C13—C14—Ti1	73.77 (12)
C8—N1—S1	120.35 (12)	C10—C14—Ti1	73.22 (11)
C8—N1—Ti1	132.89 (11)	C13—C14—H14	126.0
S1—N1—Ti1	101.20 (7)	C10—C14—H14	126.0
C2—C1—C6	121.88 (15)	Ti1—C14—H14	118.9
C2—C1—S1	118.81 (13)	C17—C15—C8	114.20 (16)
C6—C1—S1	119.21 (14)	C17—C15—C16	110.2 (2)
C1—C2—C3	118.53 (17)	C8—C15—C16	109.3 (2)
C1—C2—H2	120.7	C17—C15—H15	107.6
C3—C2—H2	120.7	C8—C15—H15	107.6
C4—C3—C2	121.39 (18)	C16—C15—H15	107.6
C4—C3—H3	119.3	C15—C16—H16A	109.5
C2—C3—H3	119.3	C15—C16—H16B	109.5
C3—C4—C5	119.03 (16)	H16A—C16—H16B	109.5
C3—C4—C7	120.7 (2)	C15—C16—H16C	109.5
C5—C4—C7	120.2 (2)	H16A—C16—H16C	109.5
C6—C5—C4	120.85 (18)	H16B—C16—H16C	109.5
C6—C5—H5	119.6	C15—C17—H17A	109.5
C4—C5—H5	119.6	C15—C17—H17B	109.5
C1—C6—C5	118.25 (18)	H17A—C17—H17B	109.5
C1—C6—H6	120.9	C15—C17—H17C	109.5
C5—C6—H6	120.9	H17A—C17—H17C	109.5
C4—C7—H7A	109.5	H17B—C17—H17C	109.5
O1—S1—O2—Ti1	114.88 (7)	C14—C10—C11—C12	1.6 (2)
N1—S1—O2—Ti1	−7.96 (7)	C9—C10—C11—C12	175.92 (18)
C1—S1—O2—Ti1	−124.24 (7)	Ti1—C10—C11—C12	65.48 (13)
N1—Ti1—O2—S1	6.93 (6)	C14—C10—C11—Ti1	−63.91 (12)
Cl1—Ti1—O2—S1	122.71 (6)	C9—C10—C11—Ti1	110.44 (18)
Cl2—Ti1—O2—S1	−127.71 (6)	N1—Ti1—C11—C12	−165.81 (12)
C11—Ti1—O2—S1	52.40 (14)	O2—Ti1—C11—C12	153.81 (13)
C14—Ti1—O2—S1	−51.14 (11)	Cl1—Ti1—C11—C12	84.05 (12)
C12—Ti1—O2—S1	141.4 (2)	Cl2—Ti1—C11—C12	−26.04 (15)
C10—Ti1—O2—S1	−0.55 (11)	C14—Ti1—C11—C12	−78.00 (14)
C13—Ti1—O2—S1	−107.13 (16)	C10—Ti1—C11—C12	−115.71 (16)
O1—S1—N1—C8	40.15 (15)	C13—Ti1—C11—C12	−36.72 (13)
O2—S1—N1—C8	166.12 (13)	N1—Ti1—C11—C10	−50.10 (11)
C1—S1—N1—C8	−81.90 (15)	O2—Ti1—C11—C10	−90.48 (14)
O1—S1—N1—Ti1	−116.77 (8)	Cl1—Ti1—C11—C10	−160.24 (10)
O2—S1—N1—Ti1	9.20 (8)	Cl2—Ti1—C11—C10	89.68 (12)
C1—S1—N1—Ti1	121.18 (8)	C14—Ti1—C11—C10	37.72 (11)
O2—Ti1—N1—C8	−158.94 (17)	C12—Ti1—C11—C10	115.71 (16)
Cl1—Ti1—N1—C8	128.72 (14)	C13—Ti1—C11—C10	78.99 (12)
Cl2—Ti1—N1—C8	−103.85 (15)	C10—C11—C12—C13	−0.3 (2)
C11—Ti1—N1—C8	43.24 (16)	Ti1—C11—C12—C13	65.22 (14)
C14—Ti1—N1—C8	−14.39 (16)	C10—C11—C12—Ti1	−65.49 (13)
C12—Ti1—N1—C8	33.55 (18)	N1—Ti1—C12—C13	−98.70 (14)
C10—Ti1—N1—C8	15.35 (15)	O2—Ti1—C12—C13	133.0 (2)
C13—Ti1—N1—C8	−7.27 (18)	Cl1—Ti1—C12—C13	151.74 (14)
O2—Ti1—N1—S1	−6.45 (6)	Cl2—Ti1—C12—C13	45.37 (14)
Cl1—Ti1—N1—S1	−78.78 (7)	C11—Ti1—C12—C13	−116.0 (2)
Cl2—Ti1—N1—S1	48.65 (8)	C14—Ti1—C12—C13	−36.83 (13)
C11—Ti1—N1—S1	−164.26 (7)	C10—Ti1—C12—C13	−78.45 (15)
C14—Ti1—N1—S1	138.11 (8)	N1—Ti1—C12—C11	17.26 (15)
C12—Ti1—N1—S1	−173.96 (7)	O2—Ti1—C12—C11	−111.0 (2)
C10—Ti1—N1—S1	167.84 (9)	Cl1—Ti1—C12—C11	−92.30 (12)
C13—Ti1—N1—S1	145.23 (8)	Cl2—Ti1—C12—C11	161.33 (11)
O1—S1—C1—C2	−9.99 (16)	C14—Ti1—C12—C11	79.13 (14)
O2—S1—C1—C2	−137.71 (14)	C10—Ti1—C12—C11	37.51 (11)
N1—S1—C1—C2	115.82 (14)	C13—Ti1—C12—C11	116.0 (2)
O1—S1—C1—C6	166.57 (13)	C11—C12—C13—C14	−1.2 (2)
O2—S1—C1—C6	38.85 (15)	Ti1—C12—C13—C14	63.08 (14)
N1—S1—C1—C6	−67.62 (15)	C11—C12—C13—Ti1	−64.25 (14)
C6—C1—C2—C3	−2.0 (3)	N1—Ti1—C13—C12	104.46 (14)
S1—C1—C2—C3	174.50 (14)	O2—Ti1—C13—C12	−155.28 (14)
C1—C2—C3—C4	0.2 (3)	Cl1—Ti1—C13—C12	−30.59 (15)
C2—C3—C4—C5	2.1 (3)	Cl2—Ti1—C13—C12	−134.77 (14)
C2—C3—C4—C7	−176.5 (2)	C11—Ti1—C13—C12	37.48 (13)
C3—C4—C5—C6	−2.7 (3)	C14—Ti1—C13—C12	117.09 (19)
C7—C4—C5—C6	175.97 (19)	C10—Ti1—C13—C12	79.17 (14)
C2—C1—C6—C5	1.4 (3)	N1—Ti1—C13—C14	−12.64 (15)
S1—C1—C6—C5	−175.05 (14)	O2—Ti1—C13—C14	87.62 (19)
C4—C5—C6—C1	0.9 (3)	Cl1—Ti1—C13—C14	−147.69 (11)
S1—N1—C8—C15	59.59 (19)	Cl2—Ti1—C13—C14	108.14 (12)
Ti1—N1—C8—C15	−152.08 (13)	C11—Ti1—C13—C14	−79.62 (13)
S1—N1—C8—C9	−176.42 (14)	C12—Ti1—C13—C14	−117.09 (19)
Ti1—N1—C8—C9	−28.1 (2)	C10—Ti1—C13—C14	−37.93 (12)
N1—C8—C9—C10	24.2 (2)	C12—C13—C14—C10	2.1 (2)
C15—C8—C9—C10	149.33 (18)	Ti1—C13—C14—C10	65.76 (13)
C8—C9—C10—C11	−103.7 (2)	C12—C13—C14—Ti1	−63.61 (14)
C8—C9—C10—C14	69.5 (3)	C11—C10—C14—C13	−2.3 (2)
C8—C9—C10—Ti1	−17.5 (2)	C9—C10—C14—C13	−176.51 (18)
N1—Ti1—C10—C11	124.95 (12)	Ti1—C10—C14—C13	−66.12 (14)
O2—Ti1—C10—C11	132.21 (10)	C11—C10—C14—Ti1	63.85 (12)
Cl1—Ti1—C10—C11	22.45 (12)	C9—C10—C14—Ti1	−110.38 (18)
Cl2—Ti1—C10—C11	−119.56 (10)	N1—Ti1—C14—C13	169.37 (13)
C14—Ti1—C10—C11	−115.24 (17)	O2—Ti1—C14—C13	−140.14 (11)
C12—Ti1—C10—C11	−37.26 (11)	Cl1—Ti1—C14—C13	49.25 (16)
C13—Ti1—C10—C11	−77.69 (12)	Cl2—Ti1—C14—C13	−68.48 (12)
N1—Ti1—C10—C14	−119.81 (13)	C11—Ti1—C14—C13	77.40 (13)
O2—Ti1—C10—C14	−112.54 (13)	C12—Ti1—C14—C13	36.14 (12)
Cl1—Ti1—C10—C14	137.69 (11)	C10—Ti1—C14—C13	115.05 (18)
Cl2—Ti1—C10—C14	−4.32 (14)	N1—Ti1—C14—C10	54.31 (12)
C11—Ti1—C10—C14	115.24 (17)	O2—Ti1—C14—C10	104.81 (13)
C12—Ti1—C10—C14	77.99 (13)	Cl1—Ti1—C14—C10	−65.80 (16)
C13—Ti1—C10—C14	37.55 (13)	Cl2—Ti1—C14—C10	176.47 (12)
N1—Ti1—C10—C9	3.47 (16)	C11—Ti1—C14—C10	−37.65 (12)
O2—Ti1—C10—C9	10.7 (2)	C12—Ti1—C14—C10	−78.91 (13)
Cl1—Ti1—C10—C9	−99.03 (17)	C13—Ti1—C14—C10	−115.05 (18)
Cl2—Ti1—C10—C9	118.96 (16)	N1—C8—C15—C17	58.4 (2)
C11—Ti1—C10—C9	−121.5 (2)	C9—C8—C15—C17	−60.9 (2)
C14—Ti1—C10—C9	123.3 (2)	N1—C8—C15—C16	−177.67 (16)
C12—Ti1—C10—C9	−158.7 (2)	C9—C8—C15—C16	63.1 (2)
C13—Ti1—C10—C9	160.8 (2)