4′-(4-Methoxy­phenyl)-1′-methyl-4′′,5′′,6′′,7′′-tetra­hydro-1H-indole-3-spiro-2′-pyrrolidine-3′-spiro-2′′-(thia­zolo­[3,2-a]­pyrimidine)-2(3H),3′′(2′′H)-dione

Li, X.-F.; Feng, Y.-Q.; Shi, D.-X.; Chen, H.-L.

doi:10.1107/S1600536803018798

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4′-(4-Methoxyphenyl)-1′-methyl-4′′,5′′,6′′,7′′-tetrahydro-1H-indole-3-spiro-2′-pyrrolidine-3′-spiro-2′′-(thiazolo[3,2-a]pyrimidine)-2(3H),3′′(2′′H)-dione

X.-F. Li, Y.-Q. Feng, D.-X. Shi and H.-L. Chen

In the title compound, C₂₄H₂₄N₄O₃S, two spiro junctions link a planar 2-oxindole ring, a pyrrolidine ring in an envelope conformation and a 6,7-dihydro-5H-thiazolo[3,2-a]pyrimidin-3-one ring. Two molecules are connected into a centrosymmetric dimer by N—H

N hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803018798/om6166sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803018798/om6166Isup2.hkl Contains datablock I

CCDC reference: 222915

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R factor = 0.048
wR factor = 0.113
Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.99

Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT301_ALERT_3_C Main Residue  Disorder .........................       9.00 Perc.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   2 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
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Spiro-compounds represent an important class of naturally occurring substances, which in many cases exhibit important biological properties (Kobayashi et al., 1991; James et al., 1991). 1,3-Dipolar cycloaddition reactions are widely used for the construction of spiro-compounds (Caramella & Grunanger, 1984). In this paper, the structure of the title compound, (I), is reported. The compound was synthesized by the intermolecular [3 + 2]-cycloaddition of azomethine ylide, derived from isatin and sarcosine by a decarboxylative route, and 2-(4-methoxy-benzylidene)-6,7- dihydro-5H-thiazolo[3,2-a]pyrimidin-3-one (Mohan & Verma, 1993).

The molecular structure of (I) is shown in Fig. 1. There exists a dispiro ring in the molecule that consists of a planar 2-oxindole ring, a pyrrolidine ring in an envelope conformation and a thiazolo[3,2-a]pyrimidine ring. Two molecules are connected into a centrosymmetric dimer by two N4—H···N2 hydrogen bonds,with an N···N distance of 2.887 (2) Å and an N—H···N angle 168.8 (3)°.

Experimental top

A mixture of 2-(4-methoxy-benzylidene)-6,7-dihydro-5H-thiazolo[3,2-a]pyrimidin-3-one (1 mmol), isatin(1 mmol) and sarcosine (1 mmol) was refluxed in methanol (60 ml) until the disappearence of the starting material, as evidenced by thin-layer chromatography. When the reaction was complete, the solvent was removed in vacuo and the residue was separated by column chromatography (silica gel, petroleum ether/ethyl acetate = 2:1), giving the title compound (I) (m.p. 506 K); IR (KBr): 3351.4 (–NH), 1723.6, 1689.2 (C═O) cm⁻¹; ¹H NMR (δ, p.p.m.): 1.15 (m, 1H, –CH₂), 1.65 (m, 1H, –CH₂), 2.27(s, 3H, N—CH₃), 3.25 (m, 2H, CH₂), 3.37 (m, 2H, CH₂), 3.63 (m, 1H, –CH₂), 3.73 (s, 3H, –CH₃) 3.99 (m, 1H, –CH₂), 4.58 (m, 1H, –CH), 6.75–7.47 (m, 8H, ArH), 8.55 (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 (Bruker, 1997); 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), drawn with 30% probability ellipsoids.
	Fig. 2. The crystal packing structure of (I), viewed along the a axis.

4'-(4-Methoxyphenyl)-1'-methyl-4'',5'',6'',7''-tetrahydro- 1H-indole-3-spiro-2'-pyrrolidine-3'-spiro-2''-(thiazolo[3,2-a]pyrimidine)- 2(3H),3''(2''H)-dione top

Crystal data top

C₂₄H₂₄N₄O₃S	Z = 2
M_r = 448.53	F(000) = 472
Triclinic, P1	D_x = 1.317 Mg m⁻³
a = 8.660 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.843 (4) Å	Cell parameters from 692 reflections
c = 14.095 (6) Å	θ = 2.5–24.7°
α = 88.374 (7)°	µ = 0.18 mm⁻¹
β = 73.054 (6)°	T = 293 K
γ = 79.895 (6)°	Plate, colorless
V = 1131.1 (8) Å³	0.30 × 0.20 × 0.10 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4585 independent reflections
Radiation source: fine-focus sealed tube	3567 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ϕ and ω scans	θ_max = 26.4°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −10→10
T_min = 0.861, T_max = 0.980	k = −12→10
6236 measured reflections	l = −10→17

Refinement top

Refinement on F²	108 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.048	w = 1/[σ²(F_o²) + (0.084P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.113	(Δ/σ)_max = 0.001
S = 1.01	Δρ_max = 0.20 e Å⁻³
4585 reflections	Δρ_min = −0.29 e Å⁻³
301 parameters

Crystal data top

C₂₄H₂₄N₄O₃S	γ = 79.895 (6)°
M_r = 448.53	V = 1131.1 (8) Å³
Triclinic, P1	Z = 2
a = 8.660 (3) Å	Mo Kα radiation
b = 9.843 (4) Å	µ = 0.18 mm⁻¹
c = 14.095 (6) Å	T = 293 K
α = 88.374 (7)°	0.30 × 0.20 × 0.10 mm
β = 73.054 (6)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4585 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	3567 reflections with I > 2σ(I)
T_min = 0.861, T_max = 0.980	R_int = 0.022
6236 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	108 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 1.01	Δρ_max = 0.20 e Å⁻³
4585 reflections	Δρ_min = −0.29 e Å⁻³
301 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	Occ. (<1)
S1	0.17279 (7)	0.48132 (5)	0.78150 (4)	0.04061 (17)
N1	0.0633 (2)	0.73428 (16)	0.74710 (12)	0.0368 (4)
N2	0.1719 (2)	0.70369 (18)	0.88471 (14)	0.0478 (5)
N3	−0.2052 (2)	0.42959 (18)	0.69077 (13)	0.0412 (4)
N4	−0.2093 (2)	0.44108 (19)	0.94013 (13)	0.0480 (5)
H4	−0.2108	0.4047	0.9965	0.058*
O1	−0.03686 (18)	0.71265 (15)	0.61675 (11)	0.0462 (4)
O2	−0.0636 (2)	0.25542 (15)	0.83935 (12)	0.0542 (4)
O3	0.71968 (19)	0.09909 (17)	0.49748 (14)	0.0637 (5)
C1	0.0288 (2)	0.50748 (19)	0.70758 (14)	0.0320 (5)
C2	0.0158 (2)	0.6612 (2)	0.68238 (15)	0.0345 (5)
C3	0.1344 (2)	0.6583 (2)	0.81302 (15)	0.0348 (5)
C4	0.1305 (4)	0.8541 (2)	0.9028 (2)	0.0634 (7)	0.593 (6)
H4A	0.2019	0.8821	0.9375	0.076*	0.593 (6)
H4B	0.0185	0.8778	0.9449	0.076*	0.593 (6)
C5	0.1479 (6)	0.9307 (4)	0.8090 (3)	0.0564 (15)	0.593 (6)
H5A	0.2610	0.9115	0.7680	0.068*	0.593 (6)
H5B	0.1182	1.0291	0.8237	0.068*	0.593 (6)
C6	0.0346 (3)	0.8859 (2)	0.75239 (18)	0.0538 (6)	0.593 (6)
H6A	−0.0793	0.9211	0.7870	0.065*	0.593 (6)
H6B	0.0594	0.9226	0.6861	0.065*	0.593 (6)
C4'	0.1305 (4)	0.8541 (2)	0.9028 (2)	0.0634 (7)	0.407 (6)
H4C	0.2274	0.8943	0.8726	0.076*	0.407 (6)
H4D	0.0990	0.8728	0.9737	0.076*	0.407 (6)
C5'	−0.0075 (10)	0.9239 (6)	0.8623 (4)	0.072 (3)	0.407 (6)
H5C	−0.0221	1.0232	0.8708	0.086*	0.407 (6)
H5D	−0.1092	0.8941	0.8984	0.086*	0.407 (6)
C6'	0.0346 (3)	0.8859 (2)	0.75239 (18)	0.0538 (6)	0.407 (6)
H6C	−0.0553	0.9242	0.7262	0.065*	0.407 (6)
H6D	0.1321	0.9207	0.7147	0.065*	0.407 (6)
C7	−0.1483 (3)	0.4803 (2)	0.76820 (14)	0.0351 (5)
C8	−0.0660 (3)	0.3349 (2)	0.62748 (16)	0.0438 (5)
H8A	−0.0847	0.3159	0.5650	0.053*
H8B	−0.0454	0.2484	0.6602	0.053*
C9	0.0759 (3)	0.4135 (2)	0.61167 (15)	0.0373 (5)
H9	0.0715	0.4754	0.5565	0.045*
C10	0.2452 (3)	0.3260 (2)	0.58337 (15)	0.0373 (5)
C11	0.2882 (3)	0.2146 (2)	0.63801 (16)	0.0441 (6)
H11	0.2099	0.1920	0.6941	0.053*
C12	0.4439 (3)	0.1355 (2)	0.61212 (17)	0.0460 (6)
H12	0.4690	0.0610	0.6503	0.055*
C13	0.5614 (3)	0.1682 (2)	0.52925 (17)	0.0444 (6)
C14	0.5215 (3)	0.2779 (2)	0.47268 (18)	0.0519 (6)
H14	0.6000	0.2995	0.4163	0.062*
C15	0.3651 (3)	0.3561 (2)	0.49928 (17)	0.0460 (6)
H15	0.3398	0.4297	0.4604	0.055*
C16	0.7672 (3)	−0.0129 (3)	0.5549 (2)	0.0682 (8)
H16A	0.7533	0.0199	0.6209	0.102*
H16B	0.8801	−0.0524	0.5249	0.102*
H16C	0.7002	−0.0818	0.5578	0.102*
C17	−0.1319 (3)	0.3753 (2)	0.85173 (15)	0.0398 (5)
C18	−0.2866 (3)	0.5747 (2)	0.92906 (16)	0.0441 (5)
C19	−0.3804 (3)	0.6706 (3)	1.00240 (19)	0.0669 (8)
H19	−0.3945	0.6522	1.0692	0.080*
C20	−0.4520 (4)	0.7940 (3)	0.9728 (2)	0.0784 (9)
H20	−0.5145	0.8606	1.0207	0.094*
C21	−0.4335 (3)	0.8214 (3)	0.8745 (2)	0.0695 (8)
H21	−0.4846	0.9054	0.8569	0.083*
C22	−0.3393 (3)	0.7250 (2)	0.80120 (18)	0.0513 (6)
H22	−0.3284	0.7430	0.7347	0.062*
C23	−0.2625 (2)	0.6026 (2)	0.82859 (15)	0.0385 (5)
C24	−0.3579 (3)	0.3745 (3)	0.72545 (19)	0.0617 (7)
H24A	−0.3410	0.2934	0.7632	0.093*
H24B	−0.3907	0.3512	0.6694	0.093*
H24C	−0.4420	0.4428	0.7665	0.093*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0471 (3)	0.0326 (3)	0.0459 (3)	0.0021 (2)	−0.0245 (3)	0.0000 (2)
N1	0.0485 (11)	0.0292 (9)	0.0336 (9)	−0.0043 (8)	−0.0153 (8)	0.0049 (8)
N2	0.0655 (13)	0.0400 (10)	0.0439 (11)	−0.0113 (9)	−0.0238 (10)	0.0007 (9)
N3	0.0395 (10)	0.0520 (11)	0.0335 (9)	−0.0106 (9)	−0.0111 (8)	−0.0020 (9)
N4	0.0632 (13)	0.0481 (11)	0.0280 (9)	−0.0052 (10)	−0.0092 (9)	0.0061 (9)
O1	0.0580 (10)	0.0443 (9)	0.0356 (8)	0.0002 (7)	−0.0186 (8)	0.0081 (7)
O2	0.0742 (12)	0.0343 (9)	0.0488 (10)	−0.0022 (8)	−0.0143 (8)	0.0064 (7)
O3	0.0439 (10)	0.0536 (10)	0.0851 (13)	0.0012 (8)	−0.0109 (9)	−0.0003 (10)
C1	0.0363 (11)	0.0316 (10)	0.0284 (10)	−0.0005 (9)	−0.0132 (9)	0.0025 (9)
C2	0.0341 (11)	0.0371 (11)	0.0278 (10)	−0.0009 (9)	−0.0053 (9)	0.0019 (9)
C3	0.0381 (12)	0.0336 (11)	0.0326 (11)	−0.0064 (9)	−0.0102 (9)	0.0035 (9)
C4	0.096 (2)	0.0414 (14)	0.0621 (17)	−0.0125 (14)	−0.0372 (16)	−0.0047 (13)
C5	0.084 (4)	0.032 (2)	0.056 (3)	−0.019 (2)	−0.021 (3)	0.006 (2)
C6	0.0830 (18)	0.0294 (12)	0.0518 (14)	−0.0033 (12)	−0.0281 (13)	0.0064 (11)
C4'	0.096 (2)	0.0414 (14)	0.0621 (17)	−0.0125 (14)	−0.0372 (16)	−0.0047 (13)
C5'	0.120 (7)	0.032 (3)	0.063 (5)	−0.005 (4)	−0.032 (5)	−0.003 (3)
C6'	0.0830 (18)	0.0294 (12)	0.0518 (14)	−0.0033 (12)	−0.0281 (13)	0.0064 (11)
C7	0.0403 (12)	0.0353 (11)	0.0296 (10)	−0.0049 (9)	−0.0110 (9)	0.0015 (9)
C8	0.0514 (14)	0.0467 (13)	0.0339 (11)	−0.0081 (11)	−0.0130 (10)	−0.0040 (10)
C9	0.0459 (13)	0.0362 (11)	0.0286 (10)	−0.0030 (10)	−0.0116 (9)	0.0002 (9)
C10	0.0462 (13)	0.0309 (11)	0.0318 (11)	−0.0035 (9)	−0.0083 (10)	−0.0043 (9)
C11	0.0509 (14)	0.0364 (12)	0.0385 (12)	−0.0038 (10)	−0.0055 (10)	0.0017 (10)
C12	0.0560 (15)	0.0346 (12)	0.0468 (13)	−0.0024 (11)	−0.0174 (12)	0.0026 (11)
C13	0.0417 (13)	0.0364 (12)	0.0522 (14)	−0.0026 (10)	−0.0108 (11)	−0.0084 (11)
C14	0.0463 (14)	0.0506 (14)	0.0488 (14)	−0.0078 (11)	0.0010 (11)	0.0028 (12)
C15	0.0522 (14)	0.0370 (12)	0.0423 (13)	−0.0044 (11)	−0.0060 (11)	0.0049 (10)
C16	0.0555 (16)	0.0524 (16)	0.097 (2)	0.0062 (13)	−0.0310 (16)	−0.0047 (15)
C17	0.0445 (13)	0.0400 (12)	0.0339 (12)	−0.0084 (10)	−0.0098 (10)	0.0048 (10)
C18	0.0458 (13)	0.0462 (13)	0.0357 (12)	−0.0054 (11)	−0.0061 (10)	−0.0007 (10)
C19	0.0779 (19)	0.0689 (18)	0.0375 (14)	0.0027 (15)	0.0003 (13)	−0.0070 (13)
C20	0.079 (2)	0.0662 (19)	0.0664 (19)	0.0158 (16)	0.0012 (16)	−0.0184 (16)
C21	0.0606 (17)	0.0540 (16)	0.075 (2)	0.0179 (13)	−0.0070 (15)	0.0002 (15)
C22	0.0418 (14)	0.0556 (15)	0.0489 (14)	0.0043 (11)	−0.0096 (11)	0.0057 (12)
C23	0.0341 (12)	0.0420 (12)	0.0353 (11)	−0.0017 (9)	−0.0066 (9)	−0.0016 (10)
C24	0.0533 (15)	0.0798 (19)	0.0565 (16)	−0.0260 (14)	−0.0140 (13)	−0.0045 (14)

Geometric parameters (Å, º) top

S1—C3	1.760 (2)	C8—C9	1.524 (3)
S1—C1	1.826 (2)	C8—H8A	0.9700
N1—C2	1.371 (3)	C8—H8B	0.9700
N1—C3	1.391 (3)	C9—C10	1.512 (3)
N1—C6	1.470 (3)	C9—H9	0.9800
N2—C3	1.263 (3)	C10—C11	1.382 (3)
N2—C4	1.472 (3)	C10—C15	1.393 (3)
N3—C7	1.454 (3)	C11—C12	1.385 (3)
N3—C24	1.463 (3)	C11—H11	0.9300
N3—C8	1.464 (3)	C12—C13	1.380 (3)
N4—C17	1.352 (3)	C12—H12	0.9300
N4—C18	1.393 (3)	C13—C14	1.379 (3)
N4—H4	0.8600	C14—C15	1.387 (3)
O1—C2	1.208 (2)	C14—H14	0.9300
O2—C17	1.216 (2)	C15—H15	0.9300
O3—C13	1.369 (3)	C16—H16A	0.9600
O3—C16	1.423 (3)	C16—H16B	0.9600
C1—C2	1.537 (3)	C16—H16C	0.9600
C1—C9	1.571 (3)	C18—C19	1.384 (3)
C1—C7	1.588 (3)	C18—C23	1.396 (3)
C4—C5	1.484 (4)	C19—C20	1.375 (4)
C4—H4A	0.9700	C19—H19	0.9300
C4—H4B	0.9700	C20—C21	1.372 (4)
C5—C6	1.556 (4)	C20—H20	0.9300
C5—H5A	0.9700	C21—C22	1.388 (3)
C5—H5B	0.9700	C21—H21	0.9300
C6—H6A	0.9700	C22—C23	1.373 (3)
C6—H6B	0.9700	C22—H22	0.9300
C5'—H5C	0.9700	C24—H24A	0.9600
C5'—H5D	0.9700	C24—H24B	0.9600
C7—C23	1.517 (3)	C24—H24C	0.9600
C7—C17	1.565 (3)

C3—S1—C1	91.86 (9)	C10—C9—C1	116.32 (17)
C2—N1—C3	116.85 (17)	C8—C9—C1	104.32 (16)
C2—N1—C6	123.06 (17)	C10—C9—H9	106.6
C3—N1—C6	120.01 (17)	C8—C9—H9	106.6
C3—N2—C4	116.28 (19)	C1—C9—H9	106.6
C7—N3—C24	115.37 (17)	C11—C10—C15	117.3 (2)
C7—N3—C8	106.53 (16)	C11—C10—C9	122.54 (19)
C24—N3—C8	115.04 (18)	C15—C10—C9	120.12 (19)
C17—N4—C18	112.00 (18)	C10—C11—C12	122.3 (2)
C17—N4—H4	124.0	C10—C11—H11	118.9
C18—N4—H4	124.0	C12—C11—H11	118.9
C13—O3—C16	117.7 (2)	C13—C12—C11	119.5 (2)
C2—C1—C9	111.53 (16)	C13—C12—H12	120.3
C2—C1—C7	108.33 (15)	C11—C12—H12	120.3
C9—C1—C7	104.14 (16)	O3—C13—C14	115.8 (2)
C2—C1—S1	104.03 (13)	O3—C13—C12	124.7 (2)
C9—C1—S1	116.22 (13)	C14—C13—C12	119.6 (2)
C7—C1—S1	112.54 (13)	C13—C14—C15	120.4 (2)
O1—C2—N1	124.02 (19)	C13—C14—H14	119.8
O1—C2—C1	124.39 (19)	C15—C14—H14	119.8
N1—C2—C1	111.51 (17)	C14—C15—C10	121.0 (2)
N2—C3—N1	127.53 (19)	C14—C15—H15	119.5
N2—C3—S1	122.45 (16)	C10—C15—H15	119.5
N1—C3—S1	110.00 (14)	O3—C16—H16A	109.5
N2—C4—C5	111.9 (2)	O3—C16—H16B	109.5
N2—C4—H4A	109.2	H16A—C16—H16B	109.5
C5—C4—H4A	109.2	O3—C16—H16C	109.5
N2—C4—H4B	109.2	H16A—C16—H16C	109.5
C5—C4—H4B	109.2	H16B—C16—H16C	109.5
H4A—C4—H4B	107.9	O2—C17—N4	126.1 (2)
C4—C5—C6	109.6 (3)	O2—C17—C7	126.11 (19)
C4—C5—H5A	109.7	N4—C17—C7	107.82 (17)
C6—C5—H5A	109.7	C19—C18—N4	128.3 (2)
C4—C5—H5B	109.7	C19—C18—C23	121.5 (2)
C6—C5—H5B	109.7	N4—C18—C23	110.17 (19)
H5A—C5—H5B	108.2	C20—C19—C18	117.5 (2)
N1—C6—C5	108.1 (2)	C20—C19—H19	121.2
N1—C6—H6A	110.1	C18—C19—H19	121.2
C5—C6—H6A	110.1	C21—C20—C19	121.7 (3)
N1—C6—H6B	110.1	C21—C20—H20	119.2
C5—C6—H6B	110.1	C19—C20—H20	119.2
H6A—C6—H6B	108.4	C20—C21—C22	120.6 (3)
H5C—C5'—H5D	108.3	C20—C21—H21	119.7
N3—C7—C23	114.57 (17)	C22—C21—H21	119.7
N3—C7—C17	115.01 (17)	C23—C22—C21	118.9 (2)
C23—C7—C17	101.20 (16)	C23—C22—H22	120.6
N3—C7—C1	101.89 (15)	C21—C22—H22	120.6
C23—C7—C1	115.58 (17)	C22—C23—C18	119.7 (2)
C17—C7—C1	109.03 (16)	C22—C23—C7	131.9 (2)
N3—C8—C9	103.22 (17)	C18—C23—C7	108.35 (18)
N3—C8—H8A	111.1	N3—C24—H24A	109.5
C9—C8—H8A	111.1	N3—C24—H24B	109.5
N3—C8—H8B	111.1	H24A—C24—H24B	109.5
C9—C8—H8B	111.1	N3—C24—H24C	109.5
H8A—C8—H8B	109.1	H24A—C24—H24C	109.5
C10—C9—C8	115.61 (17)	H24B—C24—H24C	109.5

C3—S1—C1—C2	21.77 (13)	S1—C1—C9—C10	−8.1 (2)
C3—S1—C1—C9	144.77 (16)	C2—C1—C9—C8	−120.53 (18)
C3—S1—C1—C7	−95.28 (14)	C7—C1—C9—C8	−3.9 (2)
C3—N1—C2—O1	−174.64 (19)	S1—C1—C9—C8	120.47 (16)
C6—N1—C2—O1	8.6 (3)	C8—C9—C10—C11	−53.1 (3)
C3—N1—C2—C1	8.6 (2)	C1—C9—C10—C11	69.8 (3)
C6—N1—C2—C1	−168.22 (19)	C8—C9—C10—C15	126.9 (2)
C9—C1—C2—O1	36.3 (3)	C1—C9—C10—C15	−110.2 (2)
C7—C1—C2—O1	−77.8 (2)	C15—C10—C11—C12	0.6 (3)
S1—C1—C2—O1	162.30 (17)	C9—C10—C11—C12	−179.5 (2)
C9—C1—C2—N1	−146.95 (17)	C10—C11—C12—C13	0.2 (3)
C7—C1—C2—N1	99.01 (19)	C16—O3—C13—C14	178.6 (2)
S1—C1—C2—N1	−20.93 (19)	C16—O3—C13—C12	−1.1 (3)
C4—N2—C3—N1	2.3 (3)	C11—C12—C13—O3	178.8 (2)
C4—N2—C3—S1	−179.34 (18)	C11—C12—C13—C14	−0.9 (3)
C2—N1—C3—N2	−172.4 (2)	O3—C13—C14—C15	−179.0 (2)
C6—N1—C3—N2	4.5 (3)	C12—C13—C14—C15	0.8 (3)
C2—N1—C3—S1	9.1 (2)	C13—C14—C15—C10	0.0 (4)
C6—N1—C3—S1	−174.03 (16)	C11—C10—C15—C14	−0.7 (3)
C1—S1—C3—N2	162.75 (19)	C9—C10—C15—C14	179.4 (2)
C1—S1—C3—N1	−18.63 (15)	C18—N4—C17—O2	−175.0 (2)
C3—N2—C4—C5	−34.8 (4)	C18—N4—C17—C7	4.0 (2)
N2—C4—C5—C6	58.6 (4)	N3—C7—C17—O2	48.6 (3)
C2—N1—C6—C5	−163.3 (2)	C23—C7—C17—O2	172.7 (2)
C3—N1—C6—C5	20.0 (3)	C1—C7—C17—O2	−65.0 (3)
C4—C5—C6—N1	−49.6 (4)	N3—C7—C17—N4	−130.37 (19)
C24—N3—C7—C23	−63.4 (2)	C23—C7—C17—N4	−6.3 (2)
C8—N3—C7—C23	167.56 (17)	C1—C7—C17—N4	115.97 (19)
C24—N3—C7—C17	53.2 (2)	C17—N4—C18—C19	178.2 (3)
C8—N3—C7—C17	−75.8 (2)	C17—N4—C18—C23	0.4 (3)
C24—N3—C7—C1	171.01 (18)	N4—C18—C19—C20	−176.5 (3)
C8—N3—C7—C1	42.01 (19)	C23—C18—C19—C20	1.2 (4)
C2—C1—C7—N3	96.72 (17)	C18—C19—C20—C21	0.8 (5)
C9—C1—C7—N3	−22.10 (19)	C19—C20—C21—C22	−0.8 (5)
S1—C1—C7—N3	−148.83 (13)	C20—C21—C22—C23	−1.2 (4)
C2—C1—C7—C23	−28.2 (2)	C21—C22—C23—C18	3.1 (4)
C9—C1—C7—C23	−146.99 (17)	C21—C22—C23—C7	−177.5 (2)
S1—C1—C7—C23	86.29 (18)	C19—C18—C23—C22	−3.2 (4)
C2—C1—C7—C17	−141.30 (16)	N4—C18—C23—C22	174.9 (2)
C9—C1—C7—C17	99.87 (18)	C19—C18—C23—C7	177.3 (2)
S1—C1—C7—C17	−26.85 (19)	N4—C18—C23—C7	−4.7 (3)
C7—N3—C8—C9	−45.6 (2)	N3—C7—C23—C22	−48.6 (3)
C24—N3—C8—C9	−174.79 (18)	C17—C7—C23—C22	−173.0 (2)
N3—C8—C9—C10	157.58 (17)	C1—C7—C23—C22	69.4 (3)
N3—C8—C9—C1	28.5 (2)	N3—C7—C23—C18	130.8 (2)
C2—C1—C9—C10	110.9 (2)	C17—C7—C23—C18	6.5 (2)
C7—C1—C9—C10	−132.52 (18)	C1—C7—C23—C18	−111.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···N2ⁱ	0.86	2.04	2.887 (4)	169

Symmetry code: (i) −x, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₄N₄O₃S
M_r	448.53
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.660 (3), 9.843 (4), 14.095 (6)
α, β, γ (°)	88.374 (7), 73.054 (6), 79.895 (6)
V (Å³)	1131.1 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.18
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.861, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	6236, 4585, 3567
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.113, 1.01
No. of reflections	4585
No. of parameters	301
No. of restraints	108
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.29

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···N2ⁱ	0.86	2.04	2.887 (4)	169

Symmetry code: (i) −x, −y+1, −z+2.

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