4′-(2,4-Di­chloro­phenyl)-1′-methyl-2,3,2′′,3′′-tetra­hydro-1H-indole-3-spiro-2′-pyrrolidine-3′-spiro-2′′-(1,3-benzimidazo­[2,1-b]­thia­zole)-2,3′′-dione

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

doi:10.1107/S1600536803018610

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4′-(2,4-Dichlorophenyl)-1′-methyl-2,3,2′′,3′′-tetrahydro-1H-indole-3-spiro-2′-pyrrolidine-3′-spiro-2′′-(1,3-benzimidazo[2,1-b]thiazole)-2,3′′-dione

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

In the title compound, C₂₆H₁₈Cl₂N₄O₂S, the two spiro junctions link a planar 2-oxindole ring, a pyrrolidine ring in an envelope conformation and a planar benzo[4,5]imidazo[2,1-b]thiazol-3-one ring. Molecules form dimers connected by N—H

N hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803018610/ob6283sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536803018610/ob6283Isup2.hkl Contains datablock I

CCDC reference: 222910

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.050
wR factor = 0.107
Data-to-parameter ratio = 15.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.99
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl2    ..  N1       =       3.26 Ang.

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

   1 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
   1 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 (James et al., 1991; Kobayashi et al., 1991). 1,3-Dipolar cycloaddition reactions are important process for the construction of spiro compounds (Caramella & Grunanger, 1984). We reported previously the structure of 1-methyl-spiro[2.3']oxindole- spiro[3.2"]benzo[4",5"]imidazo[2",1"-b]thiazol-3"-one-4-(2-chloro-phenyl)- pyrrolidine dioxane hemisolvate (Li et al., 2003). In the present paper, the structure of a related compound, viz. the title compound, (I), is reported. Compound (I) was synthesized by the intermolecular [3 + 2] cycloaddition of azomethine ylide, derived from isatin and sarcosine by a decarboxylative route, and 2-(2,4-dichloro-benzylidene) -benzo[4,5]imidazo[2,1-b]thiazol-3-one.

The molecular structure of (I) is illustrated in Fig. 1. The molecule contains dispiro rings that consist of a 2-oxindole ring, a pyrrolidine ring and a benzo[4,5] imidazo[2,1-b]thiazol-3-one ring. The pyrrolidine ring (N3/C11/C12/C1/C10) exhibits an envelope conformation, with atom C10 in the flap position. Two molecules related by a center of symmetry are connected by N—H···N hydrogen bonds (Table 1). There exists a short intermolecular Cl2···N1 contact with the distance of 3.258 (4) Å (Fig. 2).

Experimental top

A mixture of 2-(2,4-dichloro-benzylidene)-benzo[4,5] imidazo[2,1-b]thiazol-3-one (1 mmol), isatin (1 mmol) and sarcosine (1 mmol) was refluxed in methanol (60 ml) until the disappearence of the starting material was evidenced by thin-layer chromatography. After evaporation of the solvent, the residue was separated by column chromatography (silica gel; petroleum ether/ethyl acetate 5:1) to give (I) (m.p. 502–503 K). IR (KBr, cm⁻¹): 1755.5, 1684.2 (C═O), 1612.8 (C═N); ¹H-NMR (CDCl₃, p.p.m.): 2.31 (3H, s), 3.68 (1H, m), 4.26 (1H, m), 4.73 (1H, m), 6.78–7.71 (11H, m), 7.83 (1H, br). Compound (I) (20 mg) was dissolved in dioxane (15 ml) and the solution was left to evaporate at room temperature for 10 d, giving 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), with displacement ellipsoids drawn at the 30% probability.
	Fig. 2. The crystal packing structure of (I), viewed along the b axis. The dashed lines represent N—H···N hydrogen bonds and Cl···N intermolecular short contacts.

4'-(2,4-Dichlorophenyl)-1'-methyl-2,3,2'',3''-tetrahydro-1H-indole- 3-spiro-2'-pyrrolidine-3'-spiro-2''-(1,3-benzimidazo[2,1-b]thiazole)- 2,3''-dione top

Crystal data top

C₂₆H₁₈Cl₂N₄O₂S	D_x = 1.453 Mg m⁻³
M_r = 521.40	Melting point = 502–503 K
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 13.209 (6) Å	Cell parameters from 856 reflections
b = 11.107 (5) Å	θ = 2.4–26.4°
c = 17.248 (8) Å	µ = 0.39 mm⁻¹
β = 109.673 (7)°	T = 293 K
V = 2382.8 (19) Å³	Plate, colorless
Z = 4	0.24 × 0.20 × 0.18 mm
F(000) = 1072

Data collection top

Bruker CCD area-detector diffractometer	4889 independent reflections
Radiation source: fine-focus sealed tube	3385 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ϕ and ω scans	θ_max = 26.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −16→16
T_min = 0.908, T_max = 0.932	k = −9→13
13265 measured reflections	l = −20→21

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.050	w = 1/[σ²(F_o²) + (0.084P)²] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.107	(Δ/σ)_max < 0.001
S = 1.09	Δρ_max = 0.44 e Å⁻³
4889 reflections	Δρ_min = −0.46 e Å⁻³
317 parameters

Crystal data top

C₂₆H₁₈Cl₂N₄O₂S	V = 2382.8 (19) Å³
M_r = 521.40	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.209 (6) Å	µ = 0.39 mm⁻¹
b = 11.107 (5) Å	T = 293 K
c = 17.248 (8) Å	0.24 × 0.20 × 0.18 mm
β = 109.673 (7)°

Data collection top

Bruker CCD area-detector diffractometer	4889 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	3385 reflections with I > 2σ(I)
T_min = 0.908, T_max = 0.932	R_int = 0.037
13265 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.107	H-atom parameters constrained
S = 1.09	Δρ_max = 0.44 e Å⁻³
4889 reflections	Δρ_min = −0.46 e Å⁻³
317 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	0.32500 (5)	0.97881 (6)	0.04923 (4)	0.03333 (17)
Cl1	0.04228 (7)	0.89776 (8)	0.17462 (6)	0.0665 (3)
Cl2	−0.09646 (7)	1.29378 (9)	−0.00586 (6)	0.0690 (3)
N1	0.35457 (16)	0.75096 (18)	0.08640 (12)	0.0292 (5)
N2	0.33964 (17)	0.78207 (19)	−0.04591 (13)	0.0348 (5)
N3	0.45318 (16)	0.99324 (19)	0.29338 (12)	0.0328 (5)
N4	0.58799 (17)	1.07027 (19)	0.15708 (13)	0.0349 (5)
H4	0.6173	1.1204	0.1331	0.042*
O1	0.34045 (16)	0.73626 (16)	0.21417 (11)	0.0418 (5)
O2	0.45435 (15)	1.19164 (16)	0.16978 (12)	0.0439 (5)
C1	0.35248 (19)	0.9358 (2)	0.15802 (14)	0.0276 (5)
C2	0.34733 (19)	0.7967 (2)	0.15861 (15)	0.0296 (6)
C3	0.34227 (19)	0.8314 (2)	0.02277 (15)	0.0295 (6)
C4	0.3580 (2)	0.6359 (2)	0.05391 (16)	0.0325 (6)
C5	0.3689 (2)	0.5224 (2)	0.08855 (18)	0.0408 (7)
H5	0.3748	0.5103	0.1433	0.049*
C6	0.3705 (2)	0.4278 (3)	0.0367 (2)	0.0507 (8)
H6	0.3772	0.3495	0.0569	0.061*
C7	0.3623 (3)	0.4470 (3)	−0.0448 (2)	0.0528 (8)
H7	0.3639	0.3810	−0.0776	0.063*
C8	0.3517 (2)	0.5612 (3)	−0.07864 (18)	0.0461 (7)
H8	0.3464	0.5732	−0.1332	0.055*
C9	0.3493 (2)	0.6570 (2)	−0.02790 (16)	0.0337 (6)
C10	0.46830 (19)	0.9776 (2)	0.21427 (14)	0.0282 (5)
C11	0.3497 (2)	1.0535 (3)	0.27742 (16)	0.0392 (6)
H11A	0.3549	1.1385	0.2664	0.047*
H11B	0.3245	1.0448	0.3239	0.047*
C12	0.27448 (19)	0.9883 (2)	0.20112 (15)	0.0320 (6)
H12	0.2440	0.9195	0.2212	0.038*
C13	0.1808 (2)	1.0631 (2)	0.14864 (15)	0.0324 (6)
C14	0.0746 (2)	1.0288 (2)	0.13231 (16)	0.0367 (6)
C15	−0.0106 (2)	1.0988 (3)	0.08443 (18)	0.0451 (7)
H15	−0.0812	1.0736	0.0739	0.054*
C16	0.0105 (2)	1.2051 (3)	0.05301 (17)	0.0438 (7)
C17	0.1144 (2)	1.2440 (3)	0.06867 (19)	0.0473 (7)
H17	0.1281	1.3170	0.0477	0.057*
C18	0.1975 (2)	1.1729 (3)	0.11595 (17)	0.0427 (7)
H18	0.2677	1.1992	0.1265	0.051*
C19	0.5000 (2)	1.0952 (2)	0.17748 (15)	0.0313 (6)
C20	0.6258 (2)	0.9535 (2)	0.17955 (15)	0.0310 (6)
C21	0.7161 (2)	0.8993 (3)	0.17216 (17)	0.0433 (7)
H21	0.7585	0.9384	0.1464	0.052*
C22	0.7415 (2)	0.7847 (3)	0.20439 (19)	0.0494 (8)
H22	0.8020	0.7461	0.2004	0.059*
C23	0.6784 (2)	0.7267 (3)	0.24232 (18)	0.0470 (7)
H23	0.6969	0.6495	0.2633	0.056*
C24	0.5880 (2)	0.7817 (2)	0.24961 (16)	0.0384 (6)
H24	0.5468	0.7433	0.2765	0.046*
C25	0.56035 (19)	0.8947 (2)	0.21612 (14)	0.0288 (5)
C26	0.5427 (2)	1.0497 (3)	0.35727 (17)	0.0479 (8)
H26A	0.6077	1.0061	0.3633	0.072*
H26B	0.5290	1.0486	0.4085	0.072*
H26C	0.5504	1.1314	0.3421	0.072*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0439 (4)	0.0291 (3)	0.0259 (3)	0.0002 (3)	0.0104 (3)	0.0057 (3)
Cl1	0.0467 (5)	0.0536 (5)	0.0981 (7)	−0.0104 (4)	0.0228 (5)	0.0158 (5)
Cl2	0.0400 (5)	0.0802 (7)	0.0803 (6)	0.0177 (4)	0.0116 (4)	0.0265 (5)
N1	0.0345 (12)	0.0278 (11)	0.0260 (11)	−0.0002 (9)	0.0112 (9)	0.0048 (9)
N2	0.0408 (13)	0.0360 (13)	0.0284 (12)	−0.0039 (10)	0.0127 (10)	0.0019 (10)
N3	0.0315 (12)	0.0408 (13)	0.0266 (11)	0.0026 (10)	0.0105 (9)	−0.0003 (9)
N4	0.0358 (12)	0.0344 (13)	0.0391 (12)	−0.0038 (10)	0.0186 (10)	0.0053 (10)
O1	0.0591 (13)	0.0372 (11)	0.0343 (10)	−0.0047 (9)	0.0226 (10)	0.0097 (8)
O2	0.0415 (11)	0.0288 (11)	0.0619 (13)	0.0042 (9)	0.0180 (10)	0.0083 (9)
C1	0.0312 (13)	0.0303 (13)	0.0220 (12)	0.0004 (11)	0.0096 (11)	0.0065 (10)
C2	0.0275 (13)	0.0357 (15)	0.0256 (13)	−0.0023 (11)	0.0091 (11)	0.0026 (11)
C3	0.0293 (13)	0.0318 (14)	0.0271 (13)	−0.0035 (11)	0.0090 (11)	0.0036 (11)
C4	0.0307 (14)	0.0327 (15)	0.0343 (14)	−0.0005 (11)	0.0111 (12)	0.0007 (11)
C5	0.0470 (17)	0.0335 (15)	0.0423 (16)	0.0004 (13)	0.0156 (13)	0.0069 (13)
C6	0.055 (2)	0.0310 (16)	0.063 (2)	0.0021 (14)	0.0164 (17)	0.0023 (14)
C7	0.061 (2)	0.0388 (18)	0.054 (2)	0.0000 (15)	0.0146 (17)	−0.0135 (15)
C8	0.0565 (19)	0.0465 (18)	0.0344 (16)	−0.0003 (15)	0.0140 (14)	−0.0053 (13)
C9	0.0342 (15)	0.0327 (15)	0.0338 (14)	−0.0014 (12)	0.0110 (12)	−0.0005 (12)
C10	0.0277 (13)	0.0279 (13)	0.0285 (13)	0.0014 (11)	0.0089 (11)	0.0025 (10)
C11	0.0380 (15)	0.0476 (17)	0.0344 (15)	0.0052 (13)	0.0156 (13)	−0.0016 (12)
C12	0.0319 (14)	0.0340 (14)	0.0331 (14)	0.0002 (11)	0.0148 (12)	0.0015 (11)
C13	0.0296 (14)	0.0397 (15)	0.0308 (14)	0.0029 (12)	0.0139 (11)	−0.0013 (11)
C14	0.0350 (15)	0.0397 (16)	0.0369 (15)	−0.0027 (12)	0.0139 (12)	−0.0049 (12)
C15	0.0290 (15)	0.057 (2)	0.0495 (18)	−0.0019 (14)	0.0129 (14)	−0.0022 (15)
C16	0.0303 (15)	0.057 (2)	0.0434 (17)	0.0099 (14)	0.0108 (13)	0.0037 (14)
C17	0.0423 (18)	0.0470 (18)	0.0541 (19)	0.0057 (14)	0.0184 (15)	0.0137 (14)
C18	0.0298 (15)	0.0499 (18)	0.0497 (18)	0.0013 (13)	0.0152 (14)	0.0076 (14)
C19	0.0314 (14)	0.0331 (15)	0.0274 (13)	−0.0030 (12)	0.0073 (11)	0.0006 (11)
C20	0.0301 (14)	0.0349 (15)	0.0264 (13)	−0.0006 (11)	0.0076 (11)	−0.0028 (11)
C21	0.0374 (16)	0.0526 (19)	0.0445 (17)	0.0016 (14)	0.0198 (14)	−0.0047 (14)
C22	0.0386 (17)	0.054 (2)	0.0536 (19)	0.0159 (15)	0.0133 (15)	−0.0103 (15)
C23	0.0460 (18)	0.0378 (17)	0.0496 (18)	0.0144 (14)	0.0061 (15)	0.0016 (14)
C24	0.0413 (16)	0.0353 (16)	0.0365 (15)	0.0036 (13)	0.0104 (13)	0.0066 (12)
C25	0.0294 (13)	0.0312 (14)	0.0245 (13)	0.0008 (11)	0.0073 (11)	−0.0011 (10)
C26	0.0423 (17)	0.060 (2)	0.0359 (16)	0.0030 (15)	0.0054 (14)	−0.0099 (14)

Geometric parameters (Å, º) top

S1—C3	1.735 (3)	C10—C25	1.517 (3)
S1—C1	1.850 (2)	C10—C19	1.570 (3)
Cl1—C14	1.744 (3)	C11—C12	1.537 (4)
Cl2—C16	1.741 (3)	C11—H11A	0.9700
N1—C2	1.378 (3)	C11—H11B	0.9700
N1—C3	1.382 (3)	C12—C13	1.512 (3)
N1—C4	1.403 (3)	C12—H12	0.9800
N2—C3	1.295 (3)	C13—C14	1.388 (4)
N2—C9	1.420 (3)	C13—C18	1.391 (4)
N3—C10	1.455 (3)	C14—C15	1.388 (4)
N3—C26	1.459 (3)	C15—C16	1.367 (4)
N3—C11	1.463 (3)	C15—H15	0.9300
N4—C19	1.352 (3)	C16—C17	1.377 (4)
N4—C20	1.397 (3)	C17—C18	1.376 (4)
N4—H4	0.8600	C17—H17	0.9300
O1—C2	1.198 (3)	C18—H18	0.9300
O2—C19	1.214 (3)	C20—C21	1.380 (4)
C1—C2	1.547 (4)	C20—C25	1.393 (3)
C1—C12	1.572 (3)	C21—C22	1.384 (4)
C1—C10	1.581 (3)	C21—H21	0.9300
C4—C5	1.382 (4)	C22—C23	1.380 (4)
C4—C9	1.396 (4)	C22—H22	0.9300
C5—C6	1.385 (4)	C23—C24	1.385 (4)
C5—H5	0.9300	C23—H23	0.9300
C6—C7	1.389 (4)	C24—C25	1.378 (3)
C6—H6	0.9300	C24—H24	0.9300
C7—C8	1.384 (4)	C26—H26A	0.9600
C7—H7	0.9300	C26—H26B	0.9600
C8—C9	1.384 (4)	C26—H26C	0.9600
C8—H8	0.9300

C3—S1—C1	91.41 (11)	H11A—C11—H11B	109.0
C2—N1—C3	117.0 (2)	C13—C12—C11	114.6 (2)
C2—N1—C4	135.9 (2)	C13—C12—C1	117.1 (2)
C3—N1—C4	106.4 (2)	C11—C12—C1	104.03 (19)
C3—N2—C9	103.9 (2)	C13—C12—H12	106.8
C10—N3—C26	115.3 (2)	C11—C12—H12	106.8
C10—N3—C11	107.04 (19)	C1—C12—H12	106.8
C26—N3—C11	114.5 (2)	C14—C13—C18	116.5 (2)
C19—N4—C20	112.1 (2)	C14—C13—C12	122.6 (2)
C19—N4—H4	123.9	C18—C13—C12	121.0 (2)
C20—N4—H4	123.9	C15—C14—C13	121.9 (3)
C2—C1—C12	109.31 (19)	C15—C14—Cl1	116.9 (2)
C2—C1—C10	108.98 (19)	C13—C14—Cl1	121.1 (2)
C12—C1—C10	104.69 (19)	C16—C15—C14	119.1 (3)
C2—C1—S1	105.71 (16)	C16—C15—H15	120.4
C12—C1—S1	116.59 (17)	C14—C15—H15	120.4
C10—C1—S1	111.44 (15)	C15—C16—C17	121.1 (3)
O1—C2—N1	124.3 (2)	C15—C16—Cl2	119.1 (2)
O1—C2—C1	125.4 (2)	C17—C16—Cl2	119.8 (2)
N1—C2—C1	110.2 (2)	C18—C17—C16	118.7 (3)
N2—C3—N1	114.4 (2)	C18—C17—H17	120.6
N2—C3—S1	132.4 (2)	C16—C17—H17	120.6
N1—C3—S1	113.07 (18)	C17—C18—C13	122.6 (3)
C5—C4—C9	123.5 (2)	C17—C18—H18	118.7
C5—C4—N1	132.2 (2)	C13—C18—H18	118.7
C9—C4—N1	104.4 (2)	O2—C19—N4	126.2 (2)
C4—C5—C6	115.8 (3)	O2—C19—C10	126.1 (2)
C4—C5—H5	122.1	N4—C19—C10	107.7 (2)
C6—C5—H5	122.1	C21—C20—C25	121.7 (3)
C5—C6—C7	121.6 (3)	C21—C20—N4	128.2 (2)
C5—C6—H6	119.2	C25—C20—N4	110.0 (2)
C7—C6—H6	119.2	C20—C21—C22	117.6 (3)
C8—C7—C6	122.0 (3)	C20—C21—H21	121.2
C8—C7—H7	119.0	C22—C21—H21	121.2
C6—C7—H7	119.0	C23—C22—C21	121.1 (3)
C9—C8—C7	117.3 (3)	C23—C22—H22	119.4
C9—C8—H8	121.4	C21—C22—H22	119.4
C7—C8—H8	121.4	C22—C23—C24	120.9 (3)
C8—C9—C4	119.9 (2)	C22—C23—H23	119.6
C8—C9—N2	129.3 (2)	C24—C23—H23	119.6
C4—C9—N2	110.9 (2)	C25—C24—C23	118.6 (3)
N3—C10—C25	114.5 (2)	C25—C24—H24	120.7
N3—C10—C19	114.8 (2)	C23—C24—H24	120.7
C25—C10—C19	101.13 (19)	C24—C25—C20	120.0 (2)
N3—C10—C1	101.58 (18)	C24—C25—C10	131.2 (2)
C25—C10—C1	116.0 (2)	C20—C25—C10	108.7 (2)
C19—C10—C1	109.34 (18)	N3—C26—H26A	109.5
N3—C11—C12	103.9 (2)	N3—C26—H26B	109.5
N3—C11—H11A	111.0	H26A—C26—H26B	109.5
C12—C11—H11A	111.0	N3—C26—H26C	109.5
N3—C11—H11B	111.0	H26A—C26—H26C	109.5
C12—C11—H11B	111.0	H26B—C26—H26C	109.5

C3—S1—C1—C2	−13.06 (17)	C26—N3—C11—C12	172.3 (2)
C3—S1—C1—C12	−134.72 (19)	N3—C11—C12—C13	−153.4 (2)
C3—S1—C1—C10	105.20 (18)	N3—C11—C12—C1	−24.2 (2)
C3—N1—C2—O1	168.5 (2)	C2—C1—C12—C13	−116.4 (2)
C4—N1—C2—O1	−1.1 (5)	C10—C1—C12—C13	127.0 (2)
C3—N1—C2—C1	−13.0 (3)	S1—C1—C12—C13	3.4 (3)
C4—N1—C2—C1	177.4 (2)	C2—C1—C12—C11	116.0 (2)
C12—C1—C2—O1	−38.7 (3)	C10—C1—C12—C11	−0.6 (2)
C10—C1—C2—O1	75.2 (3)	S1—C1—C12—C11	−124.22 (19)
S1—C1—C2—O1	−164.9 (2)	C11—C12—C13—C14	−121.2 (3)
C12—C1—C2—N1	142.9 (2)	C1—C12—C13—C14	116.6 (3)
C10—C1—C2—N1	−103.2 (2)	C11—C12—C13—C18	57.0 (3)
S1—C1—C2—N1	16.6 (2)	C1—C12—C13—C18	−65.3 (3)
C9—N2—C3—N1	1.0 (3)	C18—C13—C14—C15	1.4 (4)
C9—N2—C3—S1	−174.4 (2)	C12—C13—C14—C15	179.6 (2)
C2—N1—C3—N2	−173.8 (2)	C18—C13—C14—Cl1	−176.2 (2)
C4—N1—C3—N2	−1.3 (3)	C12—C13—C14—Cl1	2.1 (3)
C2—N1—C3—S1	2.5 (3)	C13—C14—C15—C16	−0.6 (4)
C4—N1—C3—S1	174.92 (16)	Cl1—C14—C15—C16	177.0 (2)
C1—S1—C3—N2	−177.6 (3)	C14—C15—C16—C17	−0.6 (4)
C1—S1—C3—N1	7.00 (19)	C14—C15—C16—Cl2	−179.1 (2)
C2—N1—C4—C5	−9.6 (5)	C15—C16—C17—C18	0.9 (5)
C3—N1—C4—C5	−179.9 (3)	Cl2—C16—C17—C18	179.4 (2)
C2—N1—C4—C9	171.4 (3)	C16—C17—C18—C13	0.0 (5)
C3—N1—C4—C9	1.1 (3)	C14—C13—C18—C17	−1.1 (4)
C9—C4—C5—C6	−0.2 (4)	C12—C13—C18—C17	−179.3 (3)
N1—C4—C5—C6	−179.1 (3)	C20—N4—C19—O2	175.3 (2)
C4—C5—C6—C7	0.4 (4)	C20—N4—C19—C10	−3.8 (3)
C5—C6—C7—C8	−0.2 (5)	N3—C10—C19—O2	−50.2 (3)
C6—C7—C8—C9	−0.2 (5)	C25—C10—C19—O2	−174.1 (2)
C7—C8—C9—C4	0.4 (4)	C1—C10—C19—O2	63.1 (3)
C7—C8—C9—N2	179.7 (3)	N3—C10—C19—N4	128.9 (2)
C5—C4—C9—C8	−0.2 (4)	C25—C10—C19—N4	5.1 (2)
N1—C4—C9—C8	179.0 (2)	C1—C10—C19—N4	−117.8 (2)
C5—C4—C9—N2	−179.7 (2)	C19—N4—C20—C21	−176.6 (3)
N1—C4—C9—N2	−0.5 (3)	C19—N4—C20—C25	0.8 (3)
C3—N2—C9—C8	−179.7 (3)	C25—C20—C21—C22	−1.6 (4)
C3—N2—C9—C4	−0.2 (3)	N4—C20—C21—C22	175.4 (3)
C26—N3—C10—C25	63.0 (3)	C20—C21—C22—C23	0.2 (4)
C11—N3—C10—C25	−168.3 (2)	C21—C22—C23—C24	−0.3 (5)
C26—N3—C10—C19	−53.3 (3)	C22—C23—C24—C25	1.8 (4)
C11—N3—C10—C19	75.3 (3)	C23—C24—C25—C20	−3.2 (4)
C26—N3—C10—C1	−171.2 (2)	C23—C24—C25—C10	−179.6 (3)
C11—N3—C10—C1	−42.5 (2)	C21—C20—C25—C24	3.2 (4)
C2—C1—C10—N3	−91.7 (2)	N4—C20—C25—C24	−174.4 (2)
C12—C1—C10—N3	25.1 (2)	C21—C20—C25—C10	−179.7 (2)
S1—C1—C10—N3	152.01 (16)	N4—C20—C25—C10	2.8 (3)
C2—C1—C10—C25	33.1 (3)	N3—C10—C25—C24	48.1 (4)
C12—C1—C10—C25	150.0 (2)	C19—C10—C25—C24	172.1 (3)
S1—C1—C10—C25	−83.2 (2)	C1—C10—C25—C24	−69.8 (3)
C2—C1—C10—C19	146.60 (19)	N3—C10—C25—C20	−128.6 (2)
C12—C1—C10—C19	−96.6 (2)	C19—C10—C25—C20	−4.6 (2)
S1—C1—C10—C19	30.3 (2)	C1—C10—C25—C20	113.5 (2)
C10—N3—C11—C12	43.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···N2ⁱ	0.86	2.08	2.918 (3)	164

Symmetry code: (i) −x+1, −y+2, −z.

Experimental details

Crystal data
Chemical formula	C₂₆H₁₈Cl₂N₄O₂S
M_r	521.40
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	13.209 (6), 11.107 (5), 17.248 (8)
β (°)	109.673 (7)
V (Å³)	2382.8 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.39
Crystal size (mm)	0.24 × 0.20 × 0.18

Data collection
Diffractometer	Bruker CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.908, 0.932
No. of measured, independent and observed [I > 2σ(I)] reflections	13265, 4889, 3385
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.627

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.107, 1.09
No. of reflections	4889
No. of parameters	317
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.46

Computer programs: SMART (Bruker, 1997), SMART, 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	2.08	2.918 (3)	164

Symmetry code: (i) −x+1, −y+2, −z.

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