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

Li, X.-F.; Feng, Y.-Q.; Shi, D.-X.; Li, G.

doi:10.1107/S160053680301746X

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

X.-F. Li, Y.-Q. Feng, D.-X. Shi and G. Li

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.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680301746X/ww6106sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680301746X/ww6106Isup2.hkl Contains datablock I

CCDC reference: 222858

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (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

Comment top

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)°.

Experimental top

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.

Computing details top

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 top

	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) top

Crystal data top

C₂₂H₂₀N₄O₂S	Z = 2
M_r = 404.48	F(000) = 424
Triclinic, P1	D_x = 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) Å³	0.26 × 0.24 × 0.20 mm

Data collection top

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

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.041	w = 1/[σ²(F_o²) + (0.084P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.101	(Δ/σ)_max = 0.001
S = 1.03	Δρ_max = 0.28 e Å⁻³
4015 reflections	Δρ_min = −0.27 e Å⁻³
263 parameters

Crystal data top

C₂₂H₂₀N₄O₂S	γ = 64.091 (5)°
M_r = 404.48	V = 990.7 (6) Å³
Triclinic, P1	Z = 2
a = 8.538 (3) Å	Mo Kα radiation
b = 9.488 (3) Å	µ = 0.19 mm⁻¹
c = 14.227 (5) Å	T = 293 K
α = 86.206 (6)°	0.26 × 0.24 × 0.20 mm
β = 73.315 (6)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4015 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	3129 reflections with I > 2σ(I)
T_min = 0.938, T_max = 0.960	R_int = 0.015
5754 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.101	H-atom parameters constrained
S = 1.03	Δρ_max = 0.28 e Å⁻³
4015 reflections	Δρ_min = −0.27 e Å⁻³
263 parameters

Special details top

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
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 (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
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) top

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)

Experimental details

Crystal data
Chemical formula	C₂₂H₂₀N₄O₂S
M_r	404.48
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.538 (3), 9.488 (3), 14.227 (5)
α, β, γ (°)	86.206 (6), 73.315 (6), 64.091 (5)
V (Å³)	990.7 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.26 × 0.24 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.938, 0.960
No. of measured, independent and observed [I > 2σ(I)] reflections	5754, 4015, 3129
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.101, 1.03
No. of reflections	4015
No. of parameters	263
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.27

Computer programs: SMART (Bruker, 1997), SMART, SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.

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