2,2'-(Propane-2,2-di-yl)dibenzothia-zole.

The two symmetry-independent mol-ecules in the asymmetric unit of the title compound, C(17)H(14)N(2)S(2), have similar geometry; the dihedral angles between the least-squares planes of the benzothia-zole groups in the two mol-ecules are 83.93 (3) and 81.26 (3)°.

Related literature

For the synthesis of similar compounds, see: Avendaño et al. (1988 ▶); Kelarev et al. (2003 ▶); Babudri et al. (1986 ▶). For literature regarding nitrile hydration, see: Ahmed et al. (2009 ▶). For results on nitrile hydratase, see: Nagasawa & Yamada (1989 ▶); Kobayashi et al. (1992 ▶). For nitrile hydratase mimics, see: Noveron et al. (2001 ▶); Tyler et al. (2003 ▶); Yano et al. (2008 ▶).

Experimental

Crystal data

C17H14N2S2

M = 310.42

Triclinic,

a = 10.3791 (13) Å

b = 11.8832 (15) Å

c = 12.3391 (15) Å

α = 86.730 (2)°

β = 78.048 (2)°

γ = 80.779 (2)°

V = 1469.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.36 mm−1

T = 173 K

0.42 × 0.24 × 0.05 mm

Data collection

Bruker APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1995 ▶) T min = 0.865, T max = 0.982

17048 measured reflections

6379 independent reflections

5007 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.119

S = 1.04

6379 reflections

491 parameters

All H-atom parameters refined

Δρmax = 0.43 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810035488/ya2128sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035488/ya2128Isup2.hkl

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

C17H14N2S2	Z = 4
Mr = 310.42	F(000) = 648
Triclinic, P1	Dx = 1.403 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.3791 (13) Å	Cell parameters from 3754 reflections
b = 11.8832 (15) Å	θ = 2.4–26.4°
c = 12.3391 (15) Å	µ = 0.36 mm−1
α = 86.730 (2)°	T = 173 K
β = 78.048 (2)°	Plate, colorless
γ = 80.779 (2)°	0.42 × 0.24 × 0.05 mm
V = 1469.2 (3) Å3

Bruker APEX CCD area-detector diffractometer	6379 independent reflections
Radiation source: fine-focus sealed tube	5007 reflections with I > 2σ(I)
graphite	Rint = 0.032
phi and ω scans	θmax = 27.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1995)	h = −13→13
Tmin = 0.865, Tmax = 0.982	k = −15→15
17048 measured reflections	l = −15→15

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)] = 0.045	Hydrogen site location: difference Fourier map
wR(F2) = 0.119	All H-atom parameters refined
S = 1.04	w = 1/[σ2(Fo2) + (0.0637P)2 + 0.1616P] where P = (Fo2 + 2Fc2)/3
6379 reflections	(Δ/σ)max = 0.001
491 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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.

	x	y	z	Uiso*/Ueq
S1	0.11702 (5)	0.06830 (4)	0.74433 (5)	0.03295 (15)
S2	0.15867 (6)	0.39956 (5)	0.46027 (5)	0.03744 (16)
N1	0.07371 (17)	0.28776 (14)	0.75471 (14)	0.0285 (4)
N2	0.14744 (17)	0.18478 (14)	0.45096 (14)	0.0274 (4)
C1	−0.0143 (2)	0.12842 (18)	0.84422 (17)	0.0275 (4)
C2	−0.1057 (2)	0.0764 (2)	0.9223 (2)	0.0364 (5)
C3	−0.2036 (2)	0.1445 (2)	0.99230 (19)	0.0379 (6)
C4	−0.2109 (2)	0.2623 (2)	0.98686 (19)	0.0378 (6)
C5	−0.1214 (2)	0.3150 (2)	0.91101 (19)	0.0367 (5)
C6	−0.0223 (2)	0.24736 (17)	0.83812 (17)	0.0264 (4)
C7	0.15016 (19)	0.20478 (16)	0.70011 (16)	0.0236 (4)
C8	0.2599 (2)	0.22277 (17)	0.60006 (16)	0.0258 (4)
C9	0.19052 (19)	0.25650 (16)	0.50325 (16)	0.0248 (4)
C10	0.0816 (2)	0.24018 (17)	0.37034 (16)	0.0267 (4)
C11	0.0191 (2)	0.1870 (2)	0.30272 (19)	0.0359 (5)
C12	−0.0461 (2)	0.2534 (2)	0.2295 (2)	0.0428 (6)
C13	−0.0488 (2)	0.3704 (2)	0.2221 (2)	0.0445 (6)
C14	0.0126 (3)	0.4251 (2)	0.2877 (2)	0.0413 (6)
C15	0.0782 (2)	0.35846 (18)	0.36298 (17)	0.0305 (5)
C16	0.3328 (2)	0.3175 (2)	0.6252 (2)	0.0349 (5)
C17	0.3583 (2)	0.1129 (2)	0.5719 (2)	0.0339 (5)
S1'	0.50721 (6)	0.09629 (5)	0.85604 (5)	0.03416 (15)
S2'	0.40874 (6)	0.43208 (4)	1.12466 (5)	0.03095 (15)
N1'	0.53067 (17)	0.31085 (14)	0.83732 (14)	0.0276 (4)
N2'	0.45605 (18)	0.21160 (15)	1.14371 (15)	0.0313 (4)
C1'	0.6330 (2)	0.13756 (19)	0.75345 (17)	0.0324 (5)
C2'	0.7266 (3)	0.0710 (2)	0.6744 (2)	0.0429 (6)
C3'	0.8170 (3)	0.1245 (3)	0.6013 (2)	0.0497 (7)
C4'	0.8160 (2)	0.2417 (3)	0.6045 (2)	0.0467 (7)
C5'	0.7239 (2)	0.3082 (2)	0.68130 (19)	0.0389 (6)
C6'	0.6309 (2)	0.25492 (18)	0.75653 (17)	0.0288 (5)
C7'	0.4600 (2)	0.23898 (16)	0.89364 (16)	0.0245 (4)
C8'	0.3426 (2)	0.27369 (17)	0.98818 (17)	0.0268 (4)
C9'	0.4025 (2)	0.29371 (16)	1.08699 (17)	0.0256 (4)
C10'	0.5093 (2)	0.25520 (18)	1.22437 (17)	0.0292 (5)
C11'	0.5780 (3)	0.1898 (2)	1.2976 (2)	0.0395 (6)
C12'	0.6284 (2)	0.2443 (2)	1.3717 (2)	0.0426 (6)
C13'	0.6111 (2)	0.3625 (2)	1.37387 (19)	0.0390 (6)
C14'	0.5442 (2)	0.4291 (2)	1.30219 (19)	0.0361 (5)
C15'	0.4932 (2)	0.37455 (17)	1.22706 (17)	0.0278 (5)
C16'	0.2577 (2)	0.3819 (2)	0.9530 (2)	0.0331 (5)
C17'	0.2573 (3)	0.1780 (2)	1.0184 (2)	0.0368 (5)
H2	−0.099 (2)	−0.002 (2)	0.925 (2)	0.049 (7)*
H2'	0.727 (2)	−0.010 (2)	0.6737 (18)	0.036 (6)*
H3	−0.269 (2)	0.1105 (19)	1.045 (2)	0.042 (7)*
H3'	0.882 (3)	0.081 (2)	0.553 (2)	0.050 (7)*
H4	−0.275 (2)	0.307 (2)	1.0317 (19)	0.039 (7)*
H4'	0.874 (3)	0.278 (2)	0.551 (2)	0.066 (9)*
H5	−0.127 (2)	0.398 (2)	0.904 (2)	0.051 (7)*
H5'	0.721 (2)	0.3962 (19)	0.6852 (18)	0.038 (6)*
H11	0.023 (2)	0.109 (2)	0.307 (2)	0.045 (7)*
H11'	0.590 (3)	0.115 (2)	1.295 (2)	0.058 (8)*
H12	−0.086 (3)	0.219 (2)	0.181 (2)	0.056 (8)*
H12'	0.679 (2)	0.198 (2)	1.418 (2)	0.045 (7)*
H13	−0.091 (2)	0.410 (2)	0.163 (2)	0.043 (7)*
H13'	0.648 (2)	0.3967 (18)	1.4283 (18)	0.033 (6)*
H14	0.009 (2)	0.5014 (19)	0.2881 (18)	0.034 (6)*
H14'	0.531 (2)	0.5098 (19)	1.3029 (18)	0.033 (6)*
H16A	0.373 (2)	0.2928 (19)	0.687 (2)	0.041 (7)*
H16B	0.398 (2)	0.3325 (19)	0.5604 (19)	0.039 (6)*
H16C	0.265 (2)	0.3889 (19)	0.6484 (18)	0.036 (6)*
H16D	0.184 (2)	0.4074 (18)	1.0135 (19)	0.036 (6)*
H16E	0.223 (2)	0.3664 (18)	0.8903 (19)	0.033 (6)*
H16F	0.309 (2)	0.442 (2)	0.9308 (18)	0.033 (6)*
H17A	0.425 (2)	0.1270 (19)	0.508 (2)	0.042 (7)*
H17B	0.397 (2)	0.093 (2)	0.633 (2)	0.039 (7)*
H17C	0.316 (2)	0.052 (2)	0.5537 (19)	0.037 (6)*
H17D	0.224 (3)	0.163 (2)	0.954 (2)	0.060 (8)*
H17E	0.187 (3)	0.203 (2)	1.079 (2)	0.056 (8)*
H17F	0.308 (2)	0.110 (2)	1.0472 (19)	0.040 (7)*

	U11	U22	U33	U12	U13	U23
S1	0.0344 (3)	0.0212 (3)	0.0415 (3)	−0.0073 (2)	−0.0008 (2)	−0.0024 (2)
S2	0.0574 (4)	0.0217 (3)	0.0366 (3)	−0.0094 (3)	−0.0153 (3)	0.0029 (2)
N1	0.0336 (10)	0.0234 (9)	0.0275 (9)	−0.0048 (8)	−0.0037 (8)	0.0008 (7)
N2	0.0304 (9)	0.0253 (9)	0.0269 (9)	−0.0047 (7)	−0.0063 (8)	−0.0014 (7)
C1	0.0280 (11)	0.0306 (11)	0.0267 (11)	−0.0098 (9)	−0.0076 (9)	−0.0009 (9)
C2	0.0367 (13)	0.0360 (13)	0.0384 (13)	−0.0158 (11)	−0.0059 (10)	0.0055 (10)
C3	0.0339 (13)	0.0538 (15)	0.0284 (12)	−0.0171 (11)	−0.0057 (10)	0.0058 (11)
C4	0.0321 (12)	0.0517 (15)	0.0264 (12)	−0.0020 (11)	−0.0008 (10)	−0.0041 (11)
C5	0.0416 (13)	0.0331 (13)	0.0320 (13)	0.0000 (11)	−0.0038 (10)	−0.0021 (10)
C6	0.0275 (10)	0.0282 (11)	0.0248 (11)	−0.0043 (9)	−0.0084 (9)	0.0018 (8)
C7	0.0253 (10)	0.0234 (10)	0.0247 (10)	−0.0061 (8)	−0.0096 (8)	0.0007 (8)
C8	0.0279 (10)	0.0262 (10)	0.0244 (10)	−0.0070 (8)	−0.0062 (8)	0.0011 (8)
C9	0.0254 (10)	0.0217 (10)	0.0257 (11)	−0.0045 (8)	−0.0005 (8)	−0.0006 (8)
C10	0.0254 (10)	0.0289 (11)	0.0236 (11)	−0.0016 (9)	−0.0016 (8)	−0.0004 (8)
C11	0.0379 (13)	0.0385 (14)	0.0334 (13)	−0.0075 (11)	−0.0103 (10)	−0.0019 (10)
C12	0.0371 (13)	0.0606 (17)	0.0308 (13)	−0.0027 (12)	−0.0104 (11)	−0.0032 (12)
C13	0.0416 (14)	0.0590 (17)	0.0273 (13)	0.0082 (12)	−0.0081 (11)	0.0056 (12)
C14	0.0524 (15)	0.0316 (13)	0.0340 (13)	0.0044 (12)	−0.0054 (11)	0.0066 (10)
C15	0.0357 (12)	0.0299 (11)	0.0230 (11)	−0.0012 (9)	−0.0025 (9)	0.0009 (9)
C16	0.0353 (13)	0.0420 (14)	0.0313 (13)	−0.0176 (11)	−0.0064 (11)	−0.0010 (11)
C17	0.0293 (12)	0.0379 (13)	0.0324 (13)	0.0011 (10)	−0.0064 (10)	−0.0001 (10)
S1'	0.0426 (3)	0.0233 (3)	0.0359 (3)	−0.0007 (2)	−0.0079 (3)	−0.0062 (2)
S2'	0.0405 (3)	0.0226 (3)	0.0323 (3)	−0.0048 (2)	−0.0129 (2)	−0.0014 (2)
N1'	0.0282 (9)	0.0284 (9)	0.0259 (9)	−0.0047 (7)	−0.0033 (7)	−0.0048 (7)
N2'	0.0377 (10)	0.0258 (9)	0.0294 (10)	−0.0036 (8)	−0.0050 (8)	−0.0016 (7)
C1'	0.0316 (11)	0.0379 (12)	0.0272 (11)	0.0067 (10)	−0.0119 (9)	−0.0083 (9)
C2'	0.0430 (14)	0.0448 (15)	0.0385 (14)	0.0138 (12)	−0.0151 (12)	−0.0137 (12)
C3'	0.0353 (14)	0.078 (2)	0.0301 (14)	0.0172 (14)	−0.0085 (11)	−0.0159 (13)
C4'	0.0315 (13)	0.075 (2)	0.0299 (14)	−0.0016 (13)	−0.0028 (11)	−0.0033 (13)
C5'	0.0322 (12)	0.0533 (16)	0.0306 (12)	−0.0082 (11)	−0.0039 (10)	−0.0007 (11)
C6'	0.0263 (11)	0.0368 (12)	0.0241 (11)	−0.0021 (9)	−0.0074 (9)	−0.0047 (9)
C7'	0.0276 (10)	0.0211 (10)	0.0263 (11)	−0.0025 (8)	−0.0095 (8)	−0.0026 (8)
C8'	0.0280 (11)	0.0259 (11)	0.0260 (11)	−0.0054 (9)	−0.0026 (9)	−0.0032 (8)
C9'	0.0277 (10)	0.0218 (10)	0.0264 (11)	−0.0065 (8)	−0.0012 (8)	−0.0005 (8)
C10'	0.0300 (11)	0.0296 (11)	0.0265 (11)	−0.0052 (9)	−0.0021 (9)	0.0010 (9)
C11'	0.0457 (14)	0.0354 (14)	0.0360 (13)	−0.0018 (11)	−0.0107 (11)	0.0077 (11)
C12'	0.0401 (14)	0.0534 (16)	0.0347 (13)	−0.0059 (12)	−0.0127 (11)	0.0108 (12)
C13'	0.0375 (13)	0.0541 (16)	0.0294 (13)	−0.0155 (12)	−0.0093 (10)	−0.0007 (11)
C14'	0.0376 (13)	0.0373 (13)	0.0361 (13)	−0.0103 (11)	−0.0095 (10)	−0.0021 (10)
C15'	0.0280 (11)	0.0289 (11)	0.0255 (11)	−0.0050 (9)	−0.0029 (9)	0.0014 (9)
C16'	0.0328 (12)	0.0328 (12)	0.0327 (13)	0.0005 (10)	−0.0074 (10)	−0.0054 (10)
C17'	0.0354 (13)	0.0388 (14)	0.0380 (14)	−0.0152 (11)	−0.0029 (11)	−0.0037 (11)

S1—C1	1.726 (2)	S1'—C1'	1.731 (2)
S1—C7	1.7455 (19)	S1'—C7'	1.749 (2)
S2—C15	1.729 (2)	S2'—C15'	1.732 (2)
S2—C9	1.752 (2)	S2'—C9'	1.749 (2)
N1—C7	1.288 (2)	N1'—C7'	1.293 (3)
N1—C6	1.398 (3)	N1'—C6'	1.393 (3)
N2—C9	1.283 (2)	N2'—C9'	1.289 (3)
N2—C10	1.398 (3)	N2'—C10'	1.394 (3)
C1—C2	1.397 (3)	C1'—C6'	1.394 (3)
C1—C6	1.401 (3)	C1'—C2'	1.403 (3)
C2—C3	1.373 (3)	C2'—C3'	1.369 (4)
C2—H2	0.92 (2)	C2'—H2'	0.96 (2)
C3—C4	1.388 (3)	C3'—C4'	1.394 (4)
C3—H3	0.96 (2)	C3'—H3'	0.91 (3)
C4—C5	1.375 (3)	C4'—C5'	1.381 (3)
C4—H4	0.89 (2)	C4'—H4'	0.93 (3)
C5—C6	1.396 (3)	C5'—C6'	1.397 (3)
C5—H5	0.98 (2)	C5'—H5'	1.04 (2)
C7—C8	1.527 (3)	C7'—C8'	1.524 (3)
C8—C9	1.522 (3)	C8'—C9'	1.524 (3)
C8—C16	1.531 (3)	C8'—C16'	1.534 (3)
C8—C17	1.532 (3)	C8'—C17'	1.534 (3)
C10—C11	1.390 (3)	C10'—C11'	1.393 (3)
C10—C15	1.399 (3)	C10'—C15'	1.403 (3)
C11—C12	1.378 (3)	C11'—C12'	1.379 (3)
C11—H11	0.92 (2)	C11'—H11'	0.88 (3)
C12—C13	1.384 (4)	C12'—C13'	1.388 (4)
C12—H12	0.94 (3)	C12'—H12'	0.95 (2)
C13—C14	1.374 (4)	C13'—C14'	1.375 (3)
C13—H13	0.99 (2)	C13'—H13'	0.97 (2)
C14—C15	1.400 (3)	C14'—C15'	1.394 (3)
C14—H14	0.90 (2)	C14'—H14'	0.95 (2)
C16—H16A	0.95 (2)	C16'—H16D	0.97 (2)
C16—H16B	0.96 (2)	C16'—H16E	0.95 (2)
C16—H16C	1.02 (2)	C16'—H16F	0.95 (2)
C17—H17A	0.96 (3)	C17'—H17D	0.97 (3)
C17—H17B	0.92 (2)	C17'—H17E	0.95 (3)
C17—H17C	0.96 (2)	C17'—H17F	0.98 (2)
C1—S1—C7	89.31 (10)	C1'—S1'—C7'	88.76 (10)
C15—S2—C9	89.11 (10)	C15'—S2'—C9'	88.97 (10)
C7—N1—C6	111.00 (17)	C7'—N1'—C6'	110.43 (17)
C9—N2—C10	110.91 (17)	C9'—N2'—C10'	110.13 (18)
C2—C1—C6	120.6 (2)	C6'—C1'—C2'	121.1 (2)
C2—C1—S1	129.91 (18)	C6'—C1'—S1'	109.69 (16)
C6—C1—S1	109.51 (15)	C2'—C1'—S1'	129.2 (2)
C3—C2—C1	118.5 (2)	C3'—C2'—C1'	118.0 (3)
C3—C2—H2	122.4 (16)	C3'—C2'—H2'	122.1 (14)
C1—C2—H2	119.2 (16)	C1'—C2'—H2'	119.8 (14)
C2—C3—C4	121.0 (2)	C2'—C3'—C4'	121.2 (2)
C2—C3—H3	119.6 (14)	C2'—C3'—H3'	118.8 (17)
C4—C3—H3	119.4 (14)	C4'—C3'—H3'	119.9 (17)
C5—C4—C3	121.4 (2)	C5'—C4'—C3'	121.3 (3)
C5—C4—H4	117.6 (15)	C5'—C4'—H4'	118.2 (18)
C3—C4—H4	121.0 (15)	C3'—C4'—H4'	120.3 (18)
C4—C5—C6	118.5 (2)	C4'—C5'—C6'	118.2 (2)
C4—C5—H5	122.3 (15)	C4'—C5'—H5'	122.8 (13)
C6—C5—H5	119.1 (15)	C6'—C5'—H5'	119.0 (13)
C5—C6—N1	125.49 (19)	N1'—C6'—C1'	115.01 (19)
C5—C6—C1	120.1 (2)	N1'—C6'—C5'	124.8 (2)
N1—C6—C1	114.43 (18)	C1'—C6'—C5'	120.2 (2)
N1—C7—C8	122.99 (17)	N1'—C7'—C8'	123.16 (18)
N1—C7—S1	115.73 (15)	N1'—C7'—S1'	116.10 (15)
C8—C7—S1	121.24 (14)	C8'—C7'—S1'	120.74 (14)
C9—C8—C7	106.21 (15)	C7'—C8'—C9'	106.10 (16)
C9—C8—C16	111.35 (18)	C7'—C8'—C16'	108.99 (17)
C7—C8—C16	108.85 (17)	C9'—C8'—C16'	111.91 (17)
C9—C8—C17	108.69 (17)	C7'—C8'—C17'	110.90 (18)
C7—C8—C17	111.44 (17)	C9'—C8'—C17'	109.02 (18)
C16—C8—C17	110.24 (19)	C16'—C8'—C17'	109.87 (19)
N2—C9—C8	123.26 (18)	N2'—C9'—C8'	122.76 (18)
N2—C9—S2	115.81 (15)	N2'—C9'—S2'	116.46 (16)
C8—C9—S2	120.88 (14)	C8'—C9'—S2'	120.71 (14)
C11—C10—N2	125.01 (19)	C11'—C10'—N2'	125.0 (2)
C11—C10—C15	120.2 (2)	C11'—C10'—C15'	119.6 (2)
N2—C10—C15	114.78 (18)	N2'—C10'—C15'	115.36 (18)
C12—C11—C10	118.5 (2)	C12'—C11'—C10'	119.0 (2)
C12—C11—H11	121.8 (16)	C12'—C11'—H11'	120.9 (18)
C10—C11—H11	119.7 (16)	C10'—C11'—H11'	120.1 (18)
C11—C12—C13	121.2 (2)	C11'—C12'—C13'	120.9 (2)
C11—C12—H12	119.6 (17)	C11'—C12'—H12'	117.4 (15)
C13—C12—H12	119.2 (16)	C13'—C12'—H12'	121.6 (15)
C14—C13—C12	121.5 (2)	C14'—C13'—C12'	121.4 (2)
C14—C13—H13	122.9 (14)	C14'—C13'—H13'	121.0 (13)
C12—C13—H13	115.3 (14)	C12'—C13'—H13'	117.7 (13)
C13—C14—C15	117.8 (2)	C13'—C14'—C15'	118.0 (2)
C13—C14—H14	124.2 (14)	C13'—C14'—H14'	122.6 (13)
C15—C14—H14	117.9 (15)	C15'—C14'—H14'	119.4 (13)
C10—C15—C14	120.9 (2)	C14'—C15'—C10'	121.2 (2)
C10—C15—S2	109.38 (15)	C14'—C15'—S2'	129.73 (17)
C14—C15—S2	129.72 (19)	C10'—C15'—S2'	109.08 (15)
C8—C16—H16A	107.9 (14)	C8'—C16'—H16D	110.2 (13)
C8—C16—H16B	109.1 (13)	C8'—C16'—H16E	109.4 (13)
H16A—C16—H16B	112.0 (19)	H16D—C16'—H16E	109.8 (18)
C8—C16—H16C	109.6 (12)	C8'—C16'—H16F	111.6 (13)
H16A—C16—H16C	106.8 (18)	H16D—C16'—H16F	109.2 (18)
H16B—C16—H16C	111.4 (18)	H16E—C16'—H16F	106.7 (18)
C8—C17—H17A	109.2 (14)	C8'—C17'—H17D	108.2 (16)
C8—C17—H17B	106.9 (15)	C8'—C17'—H17E	107.9 (16)
H17A—C17—H17B	111 (2)	H17D—C17'—H17E	112 (2)
C8—C17—H17C	112.3 (14)	C8'—C17'—H17F	111.2 (13)
H17A—C17—H17C	106.9 (19)	H17D—C17'—H17F	113 (2)
H17B—C17—H17C	111 (2)	H17E—C17'—H17F	105 (2)
C7—S1—C1—C2	178.3 (2)	C7'—S1'—C1'—C6'	0.84 (15)
C7—S1—C1—C6	−0.96 (15)	C7'—S1'—C1'—C2'	−178.3 (2)
C6—C1—C2—C3	0.3 (3)	C6'—C1'—C2'—C3'	0.9 (3)
S1—C1—C2—C3	−178.91 (17)	S1'—C1'—C2'—C3'	179.97 (18)
C1—C2—C3—C4	−0.8 (4)	C1'—C2'—C3'—C4'	−0.4 (4)
C2—C3—C4—C5	0.4 (4)	C2'—C3'—C4'—C5'	0.0 (4)
C3—C4—C5—C6	0.5 (4)	C3'—C4'—C5'—C6'	0.0 (4)
C4—C5—C6—N1	178.3 (2)	C7'—N1'—C6'—C1'	0.3 (2)
C4—C5—C6—C1	−0.9 (3)	C7'—N1'—C6'—C5'	179.6 (2)
C7—N1—C6—C5	−179.0 (2)	C2'—C1'—C6'—N1'	178.42 (19)
C7—N1—C6—C1	0.2 (2)	S1'—C1'—C6'—N1'	−0.8 (2)
C2—C1—C6—C5	0.6 (3)	C2'—C1'—C6'—C5'	−0.9 (3)
S1—C1—C6—C5	179.95 (17)	S1'—C1'—C6'—C5'	179.83 (16)
C2—C1—C6—N1	−178.73 (19)	C4'—C5'—C6'—N1'	−178.8 (2)
S1—C1—C6—N1	0.7 (2)	C4'—C5'—C6'—C1'	0.4 (3)
C6—N1—C7—C8	176.71 (17)	C6'—N1'—C7'—C8'	179.98 (17)
C6—N1—C7—S1	−1.0 (2)	C6'—N1'—C7'—S1'	0.4 (2)
C1—S1—C7—N1	1.18 (16)	C1'—S1'—C7'—N1'	−0.74 (17)
C1—S1—C7—C8	−176.57 (16)	C1'—S1'—C7'—C8'	179.65 (16)
N1—C7—C8—C9	−77.6 (2)	N1'—C7'—C8'—C9'	−76.5 (2)
S1—C7—C8—C9	99.98 (17)	S1'—C7'—C8'—C9'	103.05 (17)
N1—C7—C8—C16	42.4 (3)	N1'—C7'—C8'—C16'	44.1 (3)
S1—C7—C8—C16	−140.02 (16)	S1'—C7'—C8'—C16'	−136.29 (16)
N1—C7—C8—C17	164.18 (19)	N1'—C7'—C8'—C17'	165.2 (2)
S1—C7—C8—C17	−18.2 (2)	S1'—C7'—C8'—C17'	−15.2 (2)
C10—N2—C9—C8	176.62 (17)	C10'—N2'—C9'—C8'	176.41 (17)
C10—N2—C9—S2	−0.8 (2)	C10'—N2'—C9'—S2'	−0.5 (2)
C7—C8—C9—N2	−77.1 (2)	C7'—C8'—C9'—N2'	−74.6 (2)
C16—C8—C9—N2	164.55 (19)	C16'—C8'—C9'—N2'	166.66 (19)
C17—C8—C9—N2	42.9 (3)	C17'—C8'—C9'—N2'	44.9 (3)
C7—C8—C9—S2	100.20 (17)	C7'—C8'—C9'—S2'	102.22 (17)
C16—C8—C9—S2	−18.2 (2)	C16'—C8'—C9'—S2'	−16.5 (2)
C17—C8—C9—S2	−139.79 (16)	C17'—C8'—C9'—S2'	−138.29 (17)
C15—S2—C9—N2	0.49 (17)	C15'—S2'—C9'—N2'	0.39 (17)
C15—S2—C9—C8	−176.98 (16)	C15'—S2'—C9'—C8'	−176.60 (16)
C9—N2—C10—C11	−177.3 (2)	C9'—N2'—C10'—C11'	−177.9 (2)
C9—N2—C10—C15	0.8 (2)	C9'—N2'—C10'—C15'	0.4 (3)
N2—C10—C11—C12	177.7 (2)	N2'—C10'—C11'—C12'	178.4 (2)
C15—C10—C11—C12	−0.3 (3)	C15'—C10'—C11'—C12'	0.2 (3)
C10—C11—C12—C13	0.6 (4)	C10'—C11'—C12'—C13'	0.1 (4)
C11—C12—C13—C14	−0.4 (4)	C11'—C12'—C13'—C14'	−0.4 (4)
C12—C13—C14—C15	−0.1 (4)	C12'—C13'—C14'—C15'	0.3 (4)
C11—C10—C15—C14	−0.2 (3)	C13'—C14'—C15'—C10'	0.0 (3)
N2—C10—C15—C14	−178.41 (19)	C13'—C14'—C15'—S2'	−178.20 (17)
C11—C10—C15—S2	177.81 (17)	C11'—C10'—C15'—C14'	−0.3 (3)
N2—C10—C15—S2	−0.4 (2)	N2'—C10'—C15'—C14'	−178.64 (19)
C13—C14—C15—C10	0.4 (3)	C11'—C10'—C15'—S2'	178.25 (17)
C13—C14—C15—S2	−177.15 (18)	N2'—C10'—C15'—S2'	−0.1 (2)
C9—S2—C15—C10	−0.03 (16)	C9'—S2'—C15'—C14'	178.2 (2)
C9—S2—C15—C14	177.8 (2)	C9'—S2'—C15'—C10'	−0.14 (16)