Di­chloro{η⁵:η¹-[2-(p-tolyl­sulfon­amido)­prop-1-yl]­cyclo­penta­dienyl}titanium

The title compound, [TiCl₂(C₁₅H₁₇NO₂S)], has a five-coordinate titanium bonded to the N and one O atom of the sulfon­amide tethered by a substituted two-carbon chain to a bound cyclo­penta­diene (assumed to occupy one position), and two Cl atoms. The Ti—N,O(sulfon­amide) bond lengths are 1.994 (3) and 2.334 (3) Å, respectively. The Ti—O bond passes through one face of the approximate tetrahedron formed by the other four bonds.

Key indicators

• Single-crystal X-ray study
• T = 168 K
• Mean [sigma](C-C) = 0.007 Å
• Disorder in main residue
• R factor = 0.056
• wR factor = 0.132
• Data-to-parameter ratio = 17.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



ABSTM_02  Alert C The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
          Tmin and Tmax reported:      0.710     0.895
          Tmin and Tmax expected:      0.637     0.895
          RR =      1.114
          Please check that your absorption correction is appropriate.

PLAT_301  Alert C Main Residue Disorder ........................       4.00 Perc.


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 2 Alert Level C = Please check

---

S1. Comment

The title compound, (I), is related to previously reported structures (Lensink, 1998; Lensink, Gainsford & Baxter, 2001; Lensink, Gainsford & Brandsma, 2001). The crystal structure consists of independent molecules (Fig. 1) of both enantantiomorphs to make a racemic crystal with one significant intermolecular contact: C11—H11····Cl2ⁱ is 2.80 Å for symmetry operation 3/2 - x, 1/2 + y, 3/2 - z. The titanium 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: 1.439 (3) Å; O2: 1.471 (3) Å] confirm the significant bonding of O2 to titanium; the Ti—C_g distance is 2.04 Å and lies within the narrow range 2.01–2.08 Å observed previously (Lensink, Gainsford & Baxter, 2001; Lensink, Gainsford & Brandsma, 2001; Allen & Kennard, 1993). The titanium coordination can best be described as being based on a tetrahedron formed by the cyclopentadiene, and the Cl1, Cl2 and N1 atoms with the Ti—O2 bond passing through the face formed by N1, Cl1 and Cl2; the angles subtended by O2 at the titanium to these three atoms are 64.50 (13), 79.65 (10) and 80.10 (9)°, respectively.

S2. Experimental

The title compound was prepared from the stoichiometric reaction of Ti(NMe₂)₄ with N-(2-p-tolylsulfonamido-propyl)-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

Atom C15 was disordered into two sites (A and B) with final occupancies 0.589:411 (17). All H atoms except those on methyl carbons and C8 were constrained to an isotropic displacement parameter 1.2 times that of the equivalent U of their parent atom. This factor was 1.5 times for the other 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 (Farrugia, 1997) based on ORTEPIIa (Johnson, 1976); software used to prepare material for publication: CIFTAB (Sheldrick, 1997).

Figures

Fig. 1. The molecular structure of (I) (Johnson, 1976; Farrugia, 1997). Displacement ellipsoids are drawn at the 20% probability level with the disordered methyl C atoms shown with three line bonds. H atoms (unlabelled) have arbitrary radii.

(I)

Crystal data

[TiCl2(C15H17NO2S)]	F(000) = 808
Mr = 394.16	Dx = 1.509 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1024 reflections
a = 10.874 (4) Å	θ = 3.1–25.9°
b = 13.517 (5) Å	µ = 0.93 mm^−1
c = 12.057 (4) Å	T = 168 K
β = 101.717 (5)°	Block, yellow
V = 1735.4 (10) Å^3	0.50 × 0.44 × 0.12 mm
Z = 4

Data collection

CCD area-detector diffractometer	3504 independent reflections
Radiation source: fine-focus sealed tube	2182 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.078
Detector resolution: 8.192 pixels mm^-1	θmax = 26.3°, θmin = 2.3°
ϕ and ω scans	h = −13→13
Absorption correction: multi-scan (Blessing, 1995)	k = −16→16
Tmin = 0.710, Tmax = 0.895	l = −14→15
21781 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.132	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0443P)^2 + 3.0084P] where P = (Fo^2 + 2Fc^2)/3
3504 reflections	(Δ/σ)max = 0.009
201 parameters	Δρmax = 0.52 e Å^−3
0 restraints	Δρmin = −0.41 e Å^−3

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	Occ. (<1)
Ti1	0.76496 (7)	0.26292 (6)	0.79217 (6)	0.0381 (2)
S1	0.84144 (11)	0.23930 (8)	0.58208 (9)	0.0427 (3)
Cl1	0.55497 (11)	0.28838 (13)	0.72130 (10)	0.0712 (5)
Cl2	0.79521 (17)	0.10179 (9)	0.85442 (12)	0.0768 (5)
O1	0.9433 (3)	0.1856 (3)	0.5505 (3)	0.0670 (11)
O2	0.7421 (3)	0.1814 (2)	0.6185 (3)	0.0549 (9)
N1	0.8785 (3)	0.3088 (3)	0.6919 (3)	0.0395 (8)
C1	0.7750 (4)	0.3142 (3)	0.4660 (3)	0.0360 (9)
C2	0.8168 (5)	0.3037 (4)	0.3651 (4)	0.0604 (15)
H2	0.8795	0.2563	0.3588	0.072*
C3	0.7657 (6)	0.3637 (4)	0.2736 (4)	0.0707 (17)
H3	0.7945	0.3567	0.2047	0.085*
C4	0.6740 (5)	0.4331 (3)	0.2801 (4)	0.0488 (12)
C5	0.6334 (4)	0.4419 (3)	0.3815 (4)	0.0496 (12)
H5	0.5696	0.4885	0.3875	0.060*
C6	0.6844 (4)	0.3837 (3)	0.4747 (4)	0.0454 (11)
H6	0.6571	0.3919	0.5442	0.054*
C7	0.6197 (6)	0.4986 (4)	0.1800 (4)	0.0737 (17)
H7A	0.6294	0.5681	0.2030	0.111*
H7B	0.5304	0.4834	0.1540	0.111*
H7C	0.6644	0.4865	0.1184	0.111*
C8	0.9750 (6)	0.3863 (5)	0.7047 (5)	0.087 (2)
H8	0.9224	0.4388	0.6597	0.130*
C9	0.9881 (6)	0.4325 (5)	0.8156 (5)	0.0799 (19)
H9A	0.9743	0.5046	0.8057	0.096*
H9B	1.0749	0.4223	0.8587	0.096*
C10	0.8976 (4)	0.3917 (3)	0.8823 (4)	0.0469 (11)
C11	0.7707 (5)	0.4213 (3)	0.8755 (4)	0.0521 (12)
H11	0.7303	0.4754	0.8325	0.063*
C12	0.7154 (5)	0.3577 (4)	0.9423 (4)	0.0550 (13)
H12	0.6314	0.3617	0.9532	0.066*
C13	0.8037 (5)	0.2874 (4)	0.9905 (4)	0.0576 (14)
H13	0.7912	0.2354	1.0401	0.069*
C14	0.9149 (5)	0.3074 (4)	0.9523 (4)	0.0526 (12)
H14	0.9901	0.2698	0.9709	0.063*
C15A	1.0712 (12)	0.3790 (12)	0.6351 (10)	0.081 (3)*	0.589 (17)
H151	1.1233	0.3204	0.6577	0.121*	0.589 (17)
H152	1.1241	0.4383	0.6461	0.121*	0.589 (17)
H153	1.0302	0.3734	0.5550	0.121*	0.589 (17)
C15B	1.0306 (18)	0.4286 (16)	0.6171 (14)	0.081 (3)*	0.411 (17)
H154	1.0503	0.3758	0.5677	0.121*	0.411 (17)
H155	1.1079	0.4636	0.6514	0.121*	0.411 (17)
H156	0.9714	0.4752	0.5723	0.121*	0.411 (17)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ti1	0.0434 (5)	0.0437 (5)	0.0277 (4)	−0.0051 (4)	0.0081 (3)	−0.0022 (3)
S1	0.0514 (7)	0.0435 (6)	0.0352 (6)	0.0126 (5)	0.0137 (5)	−0.0021 (5)
Cl1	0.0378 (7)	0.1377 (14)	0.0384 (7)	−0.0109 (8)	0.0085 (5)	−0.0158 (7)
Cl2	0.1282 (14)	0.0449 (7)	0.0548 (8)	−0.0139 (8)	0.0128 (8)	0.0079 (6)
O1	0.081 (3)	0.075 (2)	0.049 (2)	0.047 (2)	0.0232 (18)	0.0031 (18)
O2	0.077 (2)	0.0465 (18)	0.0444 (18)	−0.0137 (17)	0.0195 (17)	−0.0065 (15)
N1	0.038 (2)	0.046 (2)	0.0343 (19)	0.0025 (17)	0.0082 (16)	−0.0039 (16)
C1	0.040 (2)	0.034 (2)	0.033 (2)	0.0019 (19)	0.0064 (18)	−0.0062 (18)
C2	0.097 (4)	0.053 (3)	0.035 (3)	0.030 (3)	0.021 (3)	−0.005 (2)
C3	0.125 (5)	0.060 (3)	0.029 (3)	0.027 (3)	0.019 (3)	−0.005 (2)
C4	0.061 (3)	0.035 (2)	0.042 (3)	−0.004 (2)	−0.009 (2)	−0.007 (2)
C5	0.035 (3)	0.044 (3)	0.070 (3)	0.007 (2)	0.010 (2)	0.008 (2)
C6	0.042 (3)	0.048 (3)	0.051 (3)	0.005 (2)	0.022 (2)	0.000 (2)
C7	0.105 (5)	0.044 (3)	0.055 (3)	0.005 (3)	−0.022 (3)	−0.001 (3)
C8	0.085 (4)	0.120 (5)	0.068 (4)	−0.056 (4)	0.046 (3)	−0.037 (4)
C9	0.073 (4)	0.107 (5)	0.061 (4)	−0.045 (4)	0.018 (3)	−0.012 (3)
C10	0.047 (3)	0.059 (3)	0.033 (2)	−0.011 (2)	0.002 (2)	−0.011 (2)
C11	0.068 (4)	0.047 (3)	0.036 (3)	0.007 (3)	−0.002 (2)	−0.011 (2)
C12	0.047 (3)	0.082 (4)	0.037 (3)	−0.002 (3)	0.010 (2)	−0.021 (3)
C13	0.079 (4)	0.068 (3)	0.026 (2)	−0.010 (3)	0.011 (2)	−0.003 (2)
C14	0.050 (3)	0.065 (3)	0.036 (3)	0.009 (3)	−0.007 (2)	−0.003 (2)

Geometric parameters (Å, º)

Ti1—N1	1.994 (3)	C7—H7A	0.9800
Ti1—Cl1	2.2958 (16)	C7—H7B	0.9800
Ti1—Cl2	2.3055 (17)	C7—H7C	0.9800
Ti1—O2	2.334 (3)	C8—C15B	1.439 (16)
Ti1—C14	2.339 (5)	C8—C9	1.456 (7)
Ti1—C11	2.361 (5)	C8—C15A	1.472 (12)
Ti1—C13	2.366 (4)	C8—H8	1.0000
Ti1—C12	2.368 (4)	C9—C10	1.497 (7)
Ti1—C10	2.378 (4)	C9—H9A	0.9900
S1—O1	1.439 (3)	C9—H9B	0.9900
S1—O2	1.471 (3)	C10—C14	1.408 (6)
S1—N1	1.608 (3)	C10—C11	1.424 (7)
S1—C1	1.759 (4)	C11—C12	1.396 (7)
N1—C8	1.468 (6)	C11—H11	0.9500
C1—C6	1.381 (6)	C12—C13	1.392 (7)
C1—C2	1.390 (6)	C12—H12	0.9500
C2—C3	1.391 (7)	C13—C14	1.404 (7)
C2—H2	0.9500	C13—H13	0.9500
C3—C4	1.383 (7)	C14—H14	0.9500
C3—H3	0.9500	C15A—H151	0.9800
C4—C5	1.387 (6)	C15A—H152	0.9800
C4—C7	1.516 (6)	C15A—H153	0.9800
C5—C6	1.391 (6)	C15B—H154	0.9800
C5—H5	0.9500	C15B—H155	0.9800
C6—H6	0.9500	C15B—H156	0.9800
N1—Ti1—Cl1	114.78 (11)	C5—C6—H6	120.1
N1—Ti1—Cl2	115.24 (11)	C4—C7—H7A	109.5
Cl1—Ti1—Cl2	109.16 (7)	C4—C7—H7B	109.5
N1—Ti1—O2	64.50 (13)	H7A—C7—H7B	109.5
Cl1—Ti1—O2	79.65 (10)	C4—C7—H7C	109.5
Cl2—Ti1—O2	80.10 (9)	H7A—C7—H7C	109.5
N1—Ti1—C14	90.40 (17)	H7B—C7—H7C	109.5
Cl1—Ti1—C14	137.96 (13)	C15B—C8—C9	121.8 (8)
Cl2—Ti1—C14	86.82 (13)	C15B—C8—N1	127.2 (8)
O2—Ti1—C14	142.31 (16)	C9—C8—N1	109.7 (4)
N1—Ti1—C11	90.53 (16)	C15B—C8—C15A	32.2 (7)
Cl1—Ti1—C11	87.75 (13)	C9—C8—C15A	127.1 (6)
Cl2—Ti1—C11	136.79 (13)	N1—C8—C15A	117.9 (7)
O2—Ti1—C11	143.00 (14)	C15B—C8—H8	66.3
C14—Ti1—C11	57.45 (17)	C9—C8—H8	97.6
N1—Ti1—C13	124.33 (17)	N1—C8—H8	97.6
Cl1—Ti1—C13	108.36 (14)	C15A—C8—H8	97.6
Cl2—Ti1—C13	79.55 (14)	C8—C9—C10	112.4 (4)
O2—Ti1—C13	159.62 (16)	C8—C9—H9A	109.1
C14—Ti1—C13	34.73 (17)	C10—C9—H9A	109.1
C11—Ti1—C13	57.26 (17)	C8—C9—H9B	109.1
N1—Ti1—C12	124.08 (17)	C10—C9—H9B	109.1
Cl1—Ti1—C12	80.78 (13)	H9A—C9—H9B	107.8
Cl2—Ti1—C12	107.56 (15)	C14—C10—C11	105.8 (4)
O2—Ti1—C12	160.39 (16)	C14—C10—C9	126.8 (5)
C14—Ti1—C12	57.21 (17)	C11—C10—C9	126.9 (5)
C11—Ti1—C12	34.35 (16)	C14—C10—Ti1	71.1 (3)
C13—Ti1—C12	34.20 (17)	C11—C10—Ti1	71.9 (3)
N1—Ti1—C10	69.90 (15)	C9—C10—Ti1	115.4 (3)
Cl1—Ti1—C10	121.71 (13)	C12—C11—C10	108.6 (4)
Cl2—Ti1—C10	120.63 (13)	C12—C11—Ti1	73.1 (3)
O2—Ti1—C10	134.40 (14)	C10—C11—Ti1	73.2 (3)
C14—Ti1—C10	34.72 (16)	C12—C11—H11	125.7
C11—Ti1—C10	34.97 (16)	C10—C11—H11	125.7
C13—Ti1—C10	57.90 (17)	Ti1—C11—H11	119.8
C12—Ti1—C10	57.72 (17)	C13—C12—C11	108.6 (4)
O1—S1—O2	117.5 (2)	C13—C12—Ti1	72.8 (3)
O1—S1—N1	115.8 (2)	C11—C12—Ti1	72.5 (3)
O2—S1—N1	98.12 (18)	C13—C12—H12	125.7
O1—S1—C1	107.10 (19)	C11—C12—H12	125.7
O2—S1—C1	109.6 (2)	Ti1—C12—H12	120.7
N1—S1—C1	108.23 (19)	C12—C13—C14	107.4 (5)
S1—O2—Ti1	93.78 (15)	C12—C13—Ti1	73.0 (3)
C8—N1—S1	123.9 (3)	C14—C13—Ti1	71.6 (3)
C8—N1—Ti1	132.5 (3)	C12—C13—H13	126.3
S1—N1—Ti1	103.60 (18)	C14—C13—H13	126.3
C6—C1—C2	120.1 (4)	Ti1—C13—H13	120.9
C6—C1—S1	121.0 (3)	C13—C14—C10	109.5 (4)
C2—C1—S1	118.9 (3)	C13—C14—Ti1	73.7 (3)
C1—C2—C3	119.1 (4)	C10—C14—Ti1	74.2 (3)
C1—C2—H2	120.5	C13—C14—H14	125.3
C3—C2—H2	120.5	C10—C14—H14	125.3
C4—C3—C2	121.8 (4)	Ti1—C14—H14	118.7
C4—C3—H3	119.1	C8—C15A—H151	109.5
C2—C3—H3	119.1	C8—C15A—H152	109.5
C3—C4—C5	118.1 (4)	C8—C15A—H153	109.5
C3—C4—C7	121.3 (5)	C8—C15B—H154	109.5
C5—C4—C7	120.6 (5)	C8—C15B—H155	109.5
C4—C5—C6	121.2 (4)	H154—C15B—H155	109.5
C4—C5—H5	119.4	C8—C15B—H156	109.5
C6—C5—H5	119.4	H154—C15B—H156	109.5
C1—C6—C5	119.8 (4)	H155—C15B—H156	109.5
C1—C6—H6	120.1
O1—S1—O2—Ti1	124.22 (19)	C14—Ti1—C10—C9	122.5 (5)
N1—S1—O2—Ti1	−0.56 (17)	C11—Ti1—C10—C9	−123.0 (5)
C1—S1—O2—Ti1	−113.28 (17)	C13—Ti1—C10—C9	159.6 (5)
N1—Ti1—O2—S1	0.49 (15)	C12—Ti1—C10—C9	−159.8 (5)
Cl1—Ti1—O2—S1	124.49 (16)	C14—C10—C11—C12	1.6 (5)
Cl2—Ti1—O2—S1	−123.76 (16)	C9—C10—C11—C12	173.6 (4)
C14—Ti1—O2—S1	−52.3 (3)	Ti1—C10—C11—C12	65.0 (3)
C11—Ti1—O2—S1	52.5 (3)	C14—C10—C11—Ti1	−63.5 (3)
C13—Ti1—O2—S1	−120.2 (4)	C9—C10—C11—Ti1	108.5 (5)
C12—Ti1—O2—S1	121.2 (5)	N1—Ti1—C11—C12	−168.3 (3)
C10—Ti1—O2—S1	−0.2 (3)	Cl1—Ti1—C11—C12	76.9 (3)
O1—S1—N1—C8	55.1 (5)	Cl2—Ti1—C11—C12	−39.1 (4)
O2—S1—N1—C8	−179.0 (5)	O2—Ti1—C11—C12	146.3 (3)
C1—S1—N1—C8	−65.1 (5)	C14—Ti1—C11—C12	−78.2 (3)
O1—S1—N1—Ti1	−125.3 (2)	C13—Ti1—C11—C12	−36.7 (3)
O2—S1—N1—Ti1	0.7 (2)	C10—Ti1—C11—C12	−116.1 (4)
C1—S1—N1—Ti1	114.5 (2)	N1—Ti1—C11—C10	−52.2 (3)
Cl1—Ti1—N1—C8	115.2 (5)	Cl1—Ti1—C11—C10	−167.0 (3)
Cl2—Ti1—N1—C8	−116.7 (5)	Cl2—Ti1—C11—C10	77.1 (3)
O2—Ti1—N1—C8	179.1 (5)	O2—Ti1—C11—C10	−97.5 (3)
C14—Ti1—N1—C8	−30.0 (5)	C14—Ti1—C11—C10	37.9 (3)
C11—Ti1—N1—C8	27.4 (5)	C13—Ti1—C11—C10	79.5 (3)
C13—Ti1—N1—C8	−22.1 (6)	C12—Ti1—C11—C10	116.1 (4)
C12—Ti1—N1—C8	19.5 (6)	C10—C11—C12—C13	−0.7 (5)
C10—Ti1—N1—C8	−1.4 (5)	Ti1—C11—C12—C13	64.3 (3)
Cl1—Ti1—N1—S1	−64.40 (19)	C10—C11—C12—Ti1	−65.1 (3)
Cl2—Ti1—N1—S1	63.72 (19)	N1—Ti1—C12—C13	−102.5 (3)
O2—Ti1—N1—S1	−0.47 (14)	Cl1—Ti1—C12—C13	143.8 (3)
C14—Ti1—N1—S1	150.4 (2)	Cl2—Ti1—C12—C13	36.5 (3)
C11—Ti1—N1—S1	−152.2 (2)	O2—Ti1—C12—C13	147.0 (4)
C13—Ti1—N1—S1	158.27 (19)	C14—Ti1—C12—C13	−37.7 (3)
C12—Ti1—N1—S1	−160.09 (19)	C11—Ti1—C12—C13	−116.6 (4)
C10—Ti1—N1—S1	179.0 (2)	C10—Ti1—C12—C13	−79.1 (3)
O1—S1—C1—C6	−172.2 (4)	N1—Ti1—C12—C11	14.1 (4)
O2—S1—C1—C6	59.4 (4)	Cl1—Ti1—C12—C11	−99.6 (3)
N1—S1—C1—C6	−46.6 (4)	Cl2—Ti1—C12—C11	153.1 (3)
O1—S1—C1—C2	6.6 (5)	O2—Ti1—C12—C11	−96.4 (5)
O2—S1—C1—C2	−121.9 (4)	C14—Ti1—C12—C11	78.9 (3)
N1—S1—C1—C2	132.1 (4)	C13—Ti1—C12—C11	116.6 (4)
C6—C1—C2—C3	−0.4 (8)	C10—Ti1—C12—C11	37.5 (3)
S1—C1—C2—C3	−179.2 (4)	C11—C12—C13—C14	−0.4 (5)
C1—C2—C3—C4	−0.2 (9)	Ti1—C12—C13—C14	63.8 (3)
C2—C3—C4—C5	0.0 (8)	C11—C12—C13—Ti1	−64.2 (3)
C2—C3—C4—C7	179.5 (5)	N1—Ti1—C13—C12	101.7 (3)
C3—C4—C5—C6	0.9 (7)	Cl1—Ti1—C13—C12	−37.9 (3)
C7—C4—C5—C6	−178.6 (4)	Cl2—Ti1—C13—C12	−144.8 (3)
C2—C1—C6—C5	1.3 (7)	O2—Ti1—C13—C12	−148.4 (4)
S1—C1—C6—C5	−180.0 (3)	C14—Ti1—C13—C12	115.6 (5)
C4—C5—C6—C1	−1.6 (7)	C11—Ti1—C13—C12	36.9 (3)
S1—N1—C8—C15B	15.3 (16)	C10—Ti1—C13—C12	78.5 (3)
Ti1—N1—C8—C15B	−164.2 (13)	N1—Ti1—C13—C14	−13.9 (4)
S1—N1—C8—C9	−177.8 (4)	Cl1—Ti1—C13—C14	−153.5 (3)
Ti1—N1—C8—C9	2.7 (9)	Cl2—Ti1—C13—C14	99.6 (3)
S1—N1—C8—C15A	−21.5 (11)	O2—Ti1—C13—C14	96.0 (5)
Ti1—N1—C8—C15A	159.0 (8)	C11—Ti1—C13—C14	−78.7 (3)
C15B—C8—C9—C10	165.4 (12)	C12—Ti1—C13—C14	−115.6 (5)
N1—C8—C9—C10	−2.3 (8)	C10—Ti1—C13—C14	−37.0 (3)
C15A—C8—C9—C10	−155.8 (10)	C12—C13—C14—C10	1.4 (5)
C8—C9—C10—C14	86.2 (7)	Ti1—C13—C14—C10	66.1 (3)
C8—C9—C10—C11	−84.2 (7)	C12—C13—C14—Ti1	−64.7 (3)
C8—C9—C10—Ti1	1.5 (7)	C11—C10—C14—C13	−1.8 (5)
N1—Ti1—C10—C14	−122.8 (3)	C9—C10—C14—C13	−173.8 (4)
Cl1—Ti1—C10—C14	129.9 (3)	Ti1—C10—C14—C13	−65.8 (3)
Cl2—Ti1—C10—C14	−14.6 (3)	C11—C10—C14—Ti1	64.0 (3)
O2—Ti1—C10—C14	−122.1 (3)	C9—C10—C14—Ti1	−108.1 (5)
C11—Ti1—C10—C14	114.5 (4)	N1—Ti1—C14—C13	168.5 (3)
C13—Ti1—C10—C14	37.0 (3)	Cl1—Ti1—C14—C13	39.2 (4)
C12—Ti1—C10—C14	77.7 (3)	Cl2—Ti1—C14—C13	−76.2 (3)
N1—Ti1—C10—C11	122.7 (3)	O2—Ti1—C14—C13	−145.5 (3)
Cl1—Ti1—C10—C11	15.4 (3)	C11—Ti1—C14—C13	78.2 (3)
Cl2—Ti1—C10—C11	−129.1 (3)	C12—Ti1—C14—C13	37.1 (3)
O2—Ti1—C10—C11	123.4 (3)	C10—Ti1—C14—C13	116.4 (4)
C14—Ti1—C10—C11	−114.5 (4)	N1—Ti1—C14—C10	52.2 (3)
C13—Ti1—C10—C11	−77.5 (3)	Cl1—Ti1—C14—C10	−77.2 (3)
C12—Ti1—C10—C11	−36.8 (3)	Cl2—Ti1—C14—C10	167.4 (3)
N1—Ti1—C10—C9	−0.2 (4)	O2—Ti1—C14—C10	98.1 (3)
Cl1—Ti1—C10—C9	−107.6 (4)	C11—Ti1—C14—C10	−38.2 (3)
Cl2—Ti1—C10—C9	107.9 (4)	C13—Ti1—C14—C10	−116.4 (4)
O2—Ti1—C10—C9	0.4 (5)	C12—Ti1—C14—C10	−79.3 (3)