1′-Methyl-5′-phenyl-2′',3′',5′',6′′-tetra­hydro­indoline-3-spiro-3′-pyrrolidine-4′-spiro-2′'-imidazo­[2,1-b]­thia­zole-2,3′'-dione

The title compound, C₂₂H₂₀N₄O₂S, was synthesized by the intermolecular [3 + 2]-cyclo­addition of azomethine yl­ide, derived from isatin and sarcosine by a de­carboxyl­ative route, and 2-benzyl­idene-5,6-di­hydro-imidazo­[2,1-b]­thia­zol-3-one. In the mol­ecule, the two spiro junctions link a planar 2-oxoindoline ring, a pyrrolidine ring in an envelope conformation, and a 5,6-di­hydro­imidazo­[2,1-b]­thia­zol-3(2H)-one ring. Two mol­ecules are connected into a dimer by two N—H...N hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.041
• wR factor = 0.101
• Data-to-parameter ratio = 15.3

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .....       0.99

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) .       2.90 Ratio

   1 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

S1. Comment

Spiro compounds represent an important class of naturally occurring substances characterized by highly pronounced biological properties. (Kobayashi et al., 1991; James et al., 1991). 1,3-Dipolar cycloaddition reactions are important processes for the construction of spiro compounds (Caramella & Grunanger, 1984). In this paper, the structure of the title compound, (I) (Fig. 1), is reported.

There exists a dispiro ring in the molecule that consists of a 2-oxoindoline ring, a pyrrolidine ring and a 5,6-dihydro-imidazo[2,1-b]thiazol-3(2H)-one ring. The pyrrolidine ring (N3/C6/C5/C15/C14) is not planar, with an envelope conformation. Atoms C6/C5/C15/C14 are almost planar and the mean deviation from this plane is 0.038 (3) Å. Atom N3 lies 0.609 (3) Å above the C6/C5/C15/C14 plane in the pyrrolidine ring, forming the flap of the envelope. The dihedral angle between the C6/N3/C14 plane and the C6/C5/C15/C14 mean plane is 44.4 (2)°. The dihedral angle between phenyl plane (C16–C21) and C6/C5/C15/C14 plane is 97.8 (2)°. The 2-oxoindoline ring (C6–C13/N4) is nearly planar and the mean deviation from this plane is 0.032 (3) Å. The dihedral angle between 2-oxoindoline ring mean plane and C6/C5/C15/C14 plane is 101.0 (2)°.

The dihedral angle between 5,6-dihydro-imidazo[2,1-b]thiazol-3(2H)-one plane and the C6/C5/C15/C14 plane is 91.7 (3)°. Two molecules are connected into a dimer by two self-complementary N—H···N hydrogen bonds with an N···N distance of 2.904 (2) Å and an N—H···N angle of 168.6 (3)°.

S2. Experimental

A mixture of 2-benzylidene-5,6-dihydroimidazo[2,1-b]thiazol-3-one (1 mmol), isatin (1 mmol) and sarcosine (1 m mol) were refluxed in methanol (60 ml) until the starting material has disappeared, as evidenced by thin-layer chromatography. After the reaction was over the solvent was removed in vacuo and the residue was separated by column chromatography (silica gel, petroleum ether/ethylacetate = 2:1) to give the title compound, (I). M.p.519–521 K; IR (KBr): 3352.3 (–NH), 1721.3, 1686.1 (C═O) cm⁻¹; ¹H NMR (δ, p.p.m.): 1.67 (s, 4H, CH₂), 2.27 (s, 3H, N—CH₃), 3.29 (m, 1H,-CH₂), 3.92 (m, 1H, –CH₂), 4.61 (m, 1H, –CH), 6.81–7.52 (m, 9H, ArH), 7.85 (bs, 1H, –NH); 20 mg of (I) was dissolved in 15 ml dioxane; the solution was kept at room temperature for 15 d and natural evaporation gave colorless single crystals of (I) suitable for X-ray analysis.

S3. Refinement

H atoms were positioned geometrically (C—H = 0.93–0.98 Å) and refined with a riding model, with U_iso(H) = 1.2U_eq(carrier).

Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures

	Fig. 1. The molecular structure of (I), showing the atom-numbering scheme, drawn with 30% probability ellipsoids.
	Fig. 2. The crystal packing diagram of (I), viewed along a axis

(I)

Crystal data

C22H20N4O2S	Z = 2
Mr = 404.48	F(000) = 424
Triclinic, P1	Dx = 1.356 Mg m^−3
Hall symbol: -P 1	Melting point = 519–521 K
a = 8.538 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.488 (3) Å	Cell parameters from 875 reflections
c = 14.227 (5) Å	θ = 2.4–26.3°
α = 86.206 (6)°	µ = 0.19 mm^−1
β = 73.315 (6)°	T = 293 K
γ = 64.091 (5)°	Block, colorless
V = 990.7 (6) Å^3	0.26 × 0.24 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer	4015 independent reflections
Radiation source: fine-focus sealed tube	3129 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.015
ϕ and ω scans	θmax = 26.4°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −9→10
Tmin = 0.938, Tmax = 0.960	k = −11→11
5754 measured reflections	l = −17→16

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.041	w = 1/[σ^2(Fo^2) + (0.084P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.101	(Δ/σ)max = 0.001
S = 1.03	Δρmax = 0.28 e Å^−3
4015 reflections	Δρmin = −0.27 e Å^−3
263 parameters

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	1.19775 (6)	−0.06478 (5)	0.28434 (3)	0.03664 (14)
N1	1.0268 (2)	0.22874 (17)	0.25654 (11)	0.0358 (3)
N2	1.1535 (2)	0.1976 (2)	0.38000 (12)	0.0472 (4)
N3	0.8216 (2)	−0.08458 (18)	0.18404 (10)	0.0368 (4)
N4	0.7995 (2)	−0.0742 (2)	0.43256 (11)	0.0486 (4)
H4	0.8030	−0.1161	0.4879	0.058*
O1	0.92705 (18)	0.22923 (15)	0.12472 (9)	0.0421 (3)
O2	1.0097 (2)	−0.29029 (16)	0.32959 (10)	0.0534 (4)
C1	0.9923 (2)	0.16162 (19)	0.18886 (12)	0.0302 (4)
C2	0.9819 (3)	0.3911 (2)	0.28259 (16)	0.0507 (5)
H2A	0.8516	0.4562	0.3019	0.061*
H2B	1.0401	0.4364	0.2289	0.061*
C3	1.0605 (4)	0.3688 (3)	0.36989 (19)	0.0640 (6)
H3A	1.1460	0.4141	0.3581	0.077*
H3B	0.9638	0.4201	0.4296	0.077*
C4	1.1262 (2)	0.1317 (2)	0.31607 (12)	0.0332 (4)
C5	1.0417 (2)	−0.01304 (19)	0.20735 (11)	0.0282 (3)
C6	0.8627 (2)	−0.0320 (2)	0.26362 (12)	0.0313 (4)
C7	0.7085 (2)	0.1125 (2)	0.32522 (13)	0.0367 (4)
C8	0.5997 (3)	0.2570 (2)	0.29937 (17)	0.0510 (5)
H8	0.6093	0.2772	0.2336	0.061*
C9	0.4748 (3)	0.3722 (3)	0.3737 (2)	0.0710 (7)
H9	0.4023	0.4713	0.3575	0.085*
C10	0.4579 (3)	0.3410 (4)	0.4705 (2)	0.0816 (9)
H10	0.3754	0.4202	0.5191	0.098*
C11	0.5604 (3)	0.1948 (4)	0.49759 (18)	0.0703 (7)
H11	0.5458	0.1733	0.5635	0.084*
C12	0.6853 (3)	0.0816 (3)	0.42381 (14)	0.0450 (5)
C13	0.9042 (3)	−0.1522 (2)	0.34433 (13)	0.0383 (4)
C14	0.9952 (3)	−0.1979 (2)	0.12039 (13)	0.0401 (4)
H14A	0.9834	−0.2191	0.0576	0.048*
H14B	1.0425	−0.2959	0.1514	0.048*
C15	1.1159 (2)	−0.1138 (2)	0.10801 (12)	0.0326 (4)
H15	1.0856	−0.0389	0.0578	0.039*
C16	1.3183 (2)	−0.2127 (2)	0.07271 (13)	0.0358 (4)
C17	1.4080 (3)	−0.3473 (2)	0.11585 (16)	0.0496 (5)
H17	1.3421	−0.3816	0.1682	0.059*
C18	1.5948 (3)	−0.4315 (3)	0.0820 (2)	0.0641 (7)
H18	1.6535	−0.5219	0.1119	0.077*
C19	1.6936 (3)	−0.3830 (3)	0.0052 (2)	0.0710 (8)
H19	1.8194	−0.4392	−0.0170	0.085*
C20	1.6065 (3)	−0.2515 (3)	−0.0387 (2)	0.0727 (7)
H20	1.6735	−0.2185	−0.0913	0.087*
C21	1.4202 (3)	−0.1666 (3)	−0.00618 (16)	0.0538 (5)
H21	1.3626	−0.0778	−0.0375	0.065*
C22	0.6782 (3)	−0.1365 (3)	0.21529 (16)	0.0533 (5)
H22A	0.7173	−0.2287	0.2513	0.080*
H22B	0.6525	−0.1605	0.1585	0.080*
H22C	0.5705	−0.0546	0.2566	0.080*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0406 (3)	0.0316 (2)	0.0429 (3)	−0.0140 (2)	−0.0234 (2)	0.00699 (18)
N1	0.0413 (8)	0.0285 (8)	0.0397 (8)	−0.0152 (7)	−0.0153 (7)	0.0052 (6)
N2	0.0620 (11)	0.0452 (10)	0.0435 (9)	−0.0264 (9)	−0.0230 (8)	0.0022 (8)
N3	0.0386 (8)	0.0484 (9)	0.0302 (7)	−0.0240 (7)	−0.0108 (6)	0.0000 (7)
N4	0.0630 (11)	0.0628 (12)	0.0266 (8)	−0.0349 (10)	−0.0115 (8)	0.0098 (8)
O1	0.0476 (8)	0.0373 (7)	0.0358 (7)	−0.0113 (6)	−0.0176 (6)	0.0108 (6)
O2	0.0762 (10)	0.0365 (8)	0.0519 (8)	−0.0257 (8)	−0.0254 (8)	0.0134 (6)
C1	0.0274 (8)	0.0315 (9)	0.0280 (8)	−0.0112 (7)	−0.0057 (7)	0.0047 (7)
C2	0.0651 (14)	0.0314 (10)	0.0544 (12)	−0.0192 (10)	−0.0178 (11)	−0.0002 (9)
C3	0.0821 (17)	0.0428 (12)	0.0736 (16)	−0.0227 (12)	−0.0371 (13)	−0.0050 (11)
C4	0.0337 (9)	0.0377 (10)	0.0303 (9)	−0.0179 (8)	−0.0090 (7)	0.0041 (7)
C5	0.0289 (8)	0.0293 (8)	0.0262 (8)	−0.0109 (7)	−0.0109 (7)	0.0040 (7)
C6	0.0351 (9)	0.0349 (9)	0.0271 (8)	−0.0181 (8)	−0.0094 (7)	0.0039 (7)
C7	0.0328 (9)	0.0423 (10)	0.0362 (9)	−0.0203 (8)	−0.0046 (7)	−0.0022 (8)
C8	0.0342 (10)	0.0490 (12)	0.0620 (13)	−0.0153 (9)	−0.0068 (9)	0.0018 (10)
C9	0.0389 (12)	0.0544 (15)	0.099 (2)	−0.0088 (11)	−0.0046 (13)	−0.0136 (14)
C10	0.0498 (15)	0.085 (2)	0.085 (2)	−0.0192 (15)	0.0119 (14)	−0.0439 (17)
C11	0.0618 (15)	0.096 (2)	0.0442 (13)	−0.0356 (15)	0.0048 (11)	−0.0225 (13)
C12	0.0447 (11)	0.0594 (13)	0.0354 (10)	−0.0294 (10)	−0.0053 (8)	−0.0048 (9)
C13	0.0510 (11)	0.0430 (11)	0.0340 (9)	−0.0305 (10)	−0.0166 (8)	0.0099 (8)
C14	0.0472 (11)	0.0446 (11)	0.0321 (9)	−0.0223 (9)	−0.0114 (8)	−0.0032 (8)
C15	0.0364 (9)	0.0330 (9)	0.0261 (8)	−0.0127 (8)	−0.0098 (7)	0.0031 (7)
C16	0.0370 (10)	0.0320 (9)	0.0340 (9)	−0.0114 (8)	−0.0083 (8)	−0.0043 (7)
C17	0.0515 (12)	0.0378 (11)	0.0526 (12)	−0.0124 (10)	−0.0166 (10)	0.0030 (9)
C18	0.0547 (14)	0.0392 (12)	0.0841 (18)	0.0013 (11)	−0.0317 (13)	−0.0107 (12)
C19	0.0369 (12)	0.0692 (17)	0.0865 (19)	−0.0057 (12)	−0.0085 (13)	−0.0317 (15)
C20	0.0505 (14)	0.0797 (19)	0.0681 (16)	−0.0267 (14)	0.0117 (12)	−0.0099 (14)
C21	0.0469 (12)	0.0514 (13)	0.0479 (12)	−0.0165 (10)	0.0000 (10)	0.0029 (10)
C22	0.0527 (13)	0.0730 (15)	0.0493 (12)	−0.0406 (12)	−0.0137 (10)	−0.0029 (11)

Geometric parameters (Å, º)

S1—C4	1.7349 (19)	C8—C9	1.392 (3)
S1—C5	1.8471 (16)	C8—H8	0.9300
N1—C1	1.351 (2)	C9—C10	1.369 (4)
N1—C4	1.383 (2)	C9—H9	0.9300
N1—C2	1.461 (2)	C10—C11	1.379 (4)
N2—C4	1.264 (2)	C10—H10	0.9300
N2—C3	1.482 (3)	C11—C12	1.378 (3)
N3—C6	1.453 (2)	C11—H11	0.9300
N3—C22	1.458 (2)	C14—C15	1.525 (3)
N3—C14	1.462 (2)	C14—H14A	0.9700
N4—C13	1.350 (2)	C14—H14B	0.9700
N4—C12	1.392 (3)	C15—C16	1.506 (2)
N4—H4	0.8600	C15—H15	0.9800
O1—C1	1.207 (2)	C16—C17	1.380 (3)
O2—C13	1.212 (2)	C16—C21	1.384 (3)
C1—C5	1.546 (2)	C17—C18	1.382 (3)
C2—C3	1.535 (3)	C17—H17	0.9300
C2—H2A	0.9700	C18—C19	1.365 (4)
C2—H2B	0.9700	C18—H18	0.9300
C3—H3A	0.9700	C19—C20	1.361 (4)
C3—H3B	0.9700	C19—H19	0.9300
C5—C15	1.565 (2)	C20—C21	1.378 (3)
C5—C6	1.589 (2)	C20—H20	0.9300
C6—C7	1.517 (2)	C21—H21	0.9300
C6—C13	1.566 (2)	C22—H22A	0.9600
C7—C8	1.376 (3)	C22—H22B	0.9600
C7—C12	1.389 (3)	C22—H22C	0.9600
C4—S1—C5	91.48 (8)	C8—C9—H9	119.7
C1—N1—C4	118.09 (15)	C9—C10—C11	121.5 (2)
C1—N1—C2	133.35 (15)	C9—C10—H10	119.3
C4—N1—C2	108.56 (15)	C11—C10—H10	119.3
C4—N2—C3	106.19 (16)	C12—C11—C10	117.8 (2)
C6—N3—C22	114.87 (14)	C12—C11—H11	121.1
C6—N3—C14	106.50 (14)	C10—C11—H11	121.1
C22—N3—C14	115.72 (16)	C11—C12—C7	121.6 (2)
C13—N4—C12	112.32 (16)	C11—C12—N4	128.3 (2)
C13—N4—H4	123.8	C7—C12—N4	110.08 (17)
C12—N4—H4	123.8	O2—C13—N4	126.60 (17)
O1—C1—N1	124.99 (16)	O2—C13—C6	125.91 (17)
O1—C1—C5	124.53 (16)	N4—C13—C6	107.48 (16)
N1—C1—C5	110.45 (13)	N3—C14—C15	102.50 (14)
N1—C2—C3	100.80 (16)	N3—C14—H14A	111.3
N1—C2—H2A	111.6	C15—C14—H14A	111.3
C3—C2—H2A	111.6	N3—C14—H14B	111.3
N1—C2—H2B	111.6	C15—C14—H14B	111.3
C3—C2—H2B	111.6	H14A—C14—H14B	109.2
H2A—C2—H2B	109.4	C16—C15—C14	117.20 (15)
N2—C3—C2	107.43 (16)	C16—C15—C5	116.37 (14)
N2—C3—H3A	110.2	C14—C15—C5	104.19 (13)
C2—C3—H3A	110.2	C16—C15—H15	106.1
N2—C3—H3B	110.2	C14—C15—H15	106.1
C2—C3—H3B	110.2	C5—C15—H15	106.1
H3A—C3—H3B	108.5	C17—C16—C21	118.15 (18)
N2—C4—N1	116.84 (17)	C17—C16—C15	123.06 (17)
N2—C4—S1	131.68 (14)	C21—C16—C15	118.80 (17)
N1—C4—S1	111.44 (12)	C16—C17—C18	120.7 (2)
C1—C5—C15	110.84 (13)	C16—C17—H17	119.7
C1—C5—C6	109.70 (13)	C18—C17—H17	119.7
C15—C5—C6	104.13 (13)	C19—C18—C17	120.4 (2)
C1—C5—S1	104.45 (11)	C19—C18—H18	119.8
C15—C5—S1	116.56 (11)	C17—C18—H18	119.8
C6—C5—S1	111.19 (11)	C20—C19—C18	119.4 (2)
N3—C6—C7	114.95 (15)	C20—C19—H19	120.3
N3—C6—C13	114.41 (14)	C18—C19—H19	120.3
C7—C6—C13	101.22 (14)	C19—C20—C21	120.8 (2)
N3—C6—C5	102.09 (12)	C19—C20—H20	119.6
C7—C6—C5	115.30 (14)	C21—C20—H20	119.6
C13—C6—C5	109.26 (13)	C20—C21—C16	120.5 (2)
C8—C7—C12	119.87 (18)	C20—C21—H21	119.8
C8—C7—C6	131.62 (17)	C16—C21—H21	119.8
C12—C7—C6	108.50 (16)	N3—C22—H22A	109.5
C7—C8—C9	118.6 (2)	N3—C22—H22B	109.5
C7—C8—H8	120.7	H22A—C22—H22B	109.5
C9—C8—H8	120.7	N3—C22—H22C	109.5
C10—C9—C8	120.6 (2)	H22A—C22—H22C	109.5
C10—C9—H9	119.7	H22B—C22—H22C	109.5
C4—N1—C1—O1	−170.58 (16)	C5—C6—C7—C12	−111.60 (16)
C2—N1—C1—O1	8.6 (3)	C12—C7—C8—C9	3.5 (3)
C4—N1—C1—C5	11.5 (2)	C6—C7—C8—C9	−175.8 (2)
C2—N1—C1—C5	−169.29 (18)	C7—C8—C9—C10	−1.5 (4)
C1—N1—C2—C3	177.04 (19)	C8—C9—C10—C11	−1.3 (4)
C4—N1—C2—C3	−3.7 (2)	C9—C10—C11—C12	2.0 (4)
C4—N2—C3—C2	−3.4 (3)	C10—C11—C12—C7	0.1 (4)
N1—C2—C3—N2	4.3 (2)	C10—C11—C12—N4	−178.0 (2)
C3—N2—C4—N1	1.0 (2)	C8—C7—C12—C11	−2.9 (3)
C3—N2—C4—S1	178.56 (17)	C6—C7—C12—C11	176.59 (19)
C1—N1—C4—N2	−178.68 (16)	C8—C7—C12—N4	175.49 (17)
C2—N1—C4—N2	1.9 (2)	C6—C7—C12—N4	−5.0 (2)
C1—N1—C4—S1	3.28 (19)	C13—N4—C12—C11	179.6 (2)
C2—N1—C4—S1	−176.10 (13)	C13—N4—C12—C7	1.4 (2)
C5—S1—C4—N2	169.12 (19)	C12—N4—C13—O2	−176.52 (19)
C5—S1—C4—N1	−13.23 (13)	C12—N4—C13—C6	2.8 (2)
O1—C1—C5—C15	36.3 (2)	N3—C6—C13—O2	49.7 (2)
N1—C1—C5—C15	−145.82 (14)	C7—C6—C13—O2	173.93 (18)
O1—C1—C5—C6	−78.2 (2)	C5—C6—C13—O2	−64.0 (2)
N1—C1—C5—C6	99.74 (15)	N3—C6—C13—N4	−129.56 (16)
O1—C1—C5—S1	162.57 (14)	C7—C6—C13—N4	−5.35 (18)
N1—C1—C5—S1	−19.51 (16)	C5—C6—C13—N4	116.72 (16)
C4—S1—C5—C1	18.03 (11)	C6—N3—C14—C15	−46.97 (17)
C4—S1—C5—C15	140.67 (13)	C22—N3—C14—C15	−175.98 (15)
C4—S1—C5—C6	−100.22 (12)	N3—C14—C15—C16	161.85 (14)
C22—N3—C6—C7	−63.8 (2)	N3—C14—C15—C5	31.68 (16)
C14—N3—C6—C7	166.72 (14)	C1—C5—C15—C16	103.89 (17)
C22—N3—C6—C13	52.8 (2)	C6—C5—C15—C16	−138.22 (15)
C14—N3—C6—C13	−76.74 (18)	S1—C5—C15—C16	−15.4 (2)
C22—N3—C6—C5	170.66 (15)	C1—C5—C15—C14	−125.46 (14)
C14—N3—C6—C5	41.14 (16)	C6—C5—C15—C14	−7.57 (16)
C1—C5—C6—N3	99.39 (15)	S1—C5—C15—C14	115.28 (14)
C15—C5—C6—N3	−19.28 (15)	C14—C15—C16—C17	−51.3 (2)
S1—C5—C6—N3	−145.58 (11)	C5—C15—C16—C17	72.9 (2)
C1—C5—C6—C7	−25.96 (18)	C14—C15—C16—C21	129.15 (19)
C15—C5—C6—C7	−144.62 (14)	C5—C15—C16—C21	−106.6 (2)
S1—C5—C6—C7	89.07 (15)	C21—C16—C17—C18	1.2 (3)
C1—C5—C6—C13	−139.11 (14)	C15—C16—C17—C18	−178.35 (19)
C15—C5—C6—C13	102.22 (15)	C16—C17—C18—C19	−0.1 (3)
S1—C5—C6—C13	−24.08 (16)	C17—C18—C19—C20	−0.7 (4)
N3—C6—C7—C8	−50.6 (3)	C18—C19—C20—C21	0.3 (4)
C13—C6—C7—C8	−174.46 (19)	C19—C20—C21—C16	0.8 (4)
C5—C6—C7—C8	67.8 (2)	C17—C16—C21—C20	−1.5 (3)
N3—C6—C7—C12	130.01 (16)	C15—C16—C21—C20	178.0 (2)
C13—C6—C7—C12	6.16 (18)