1-{1-[(2-Chloro­thia­zol-5-yl)meth­yl]-2-[(2-chloro­thia­zol-5-yl)methyl­sulfan­yl]-4-methyl-6-phenyl-1,6-dihydro­pyrimidin-5-yl}ethanone

Zhu, X.-F.; Shi, D.-Q.; Luo, F.; Wang, Z.-F.

doi:10.1107/S1600536807033764

1-{1-[(2-Chlorothiazol-5-yl)methyl]-2-[(2-chlorothiazol-5-yl)methylsulfanyl]-4-methyl-6-phenyl-1,6-dihydropyrimidin-5-yl}ethanone

X.-F. Zhu, D.-Q. Shi, F. Luo and Z.-F. Wang

The crystal structure of the title compound, C₂₁H₁₈Cl₂N₄OS₃, is stabilized by intermolecular C—H

O and C—H

N hydrogen bonds. The dihydropyrimidine ring is almost planer, with a mean deviation from the plane of 0.132 (1) Å. The dihedral angles between the dihydropyrimidine ring and the phenyl, 1-thiazole and 2-thiazole rings are 88.5 (1), 13.6 (1) and 8.0 (1)°, respectively.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807033764/pr2011sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807033764/pr2011Isup2.hkl Contains datablock I

CCDC reference: 657781

checkCIF report

Key indicators

Single-crystal X-ray study
T = 300 K
Mean (C-C) = 0.003 Å
R factor = 0.047
wR factor = 0.134
Data-to-parameter ratio = 17.5

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT093_ALERT_1_A No su's on H-atoms, but refinement reported as .      mixed

Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.99
PLAT322_ALERT_2_C Check Hybridisation of  S1     in Main Residue .          ?
PLAT322_ALERT_2_C Check Hybridisation of  S3     in Main Residue .          ?

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C7     = ...          R

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Biginelli reaction is one of the most powerful synthetic methodologies for the heterocyclic six-membered rings. 3,4-Dihydropyrimidin-2(1H)-ones (DHPMs) and their derivatives have attracted considerable interest due to their wide range of therapeutic and pharmacological properties, such as antiviral, antitumor, antibacterial and antiinflammatory properties.(Kappe,1993).

We report here the crystal structure of (I) (Fig. 1), which was synthesized by introducing thiazole rings into a Biginelli Dihydropyrimidine molecular framework. The crystal packing shows that the intermolecular C12—H12A···N3ⁱ [symmetry code (i) -x + 1,y + 1/2,-z + 3/2] hydrogen bonds link molecules into rows along the c axis,while weak, inversion related C18—H18B···O1ⁱⁱ [symmetry code (ii) x - 1,y,z] hydrogen bonds join parallel rows forming a network, Fig, 2, Table 1.

Related literature top

For general background, see: Kappe (1993).

Experimental top

A solution of 1-(4-(4-chlorophenyl)-6-methyl-2-thioxo-1,2,3,4- tetrahydropyrimidin-5-yl)ethanone(2 mmol),2-chloro-5-chloromethyl-thiazole (4 mmol) and potassium carbonate powder (2 mmol) in anhydrous Dimethyl Formamide (10 ml)was stirred vigorously at room temperature until the reaction was complete (monitored by thin-layer chromatography), the solid filtered off and the filtrate concentrated under vacuum.The residue was purified by column chromatography on silica gel using (2:1 v/v) petroleum ether/ethyl acetate as the eluent, giving a green solid (yield 88%, m.p.412 - 414 K). A yellow crystal grown from dichloromethane and hexane (2:1 v/v) was selected for X-ray structure analysis.

Structure description top

For general background, see: Kappe (1993).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; 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 structure of (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. Crystal packing of (I).Intermolecular C—H···N and C—H···O interactions (dashed lines). Other H atoms have been omitted for clarity. [Symmetry codes:(i) -x + 1,y + 1/2,-z + 3/2;(ii) x - 1,y,z.]

1-{1-[(2-Chlorothiazol-5-yl)methyl]-2-[(2-chlorothiazol-5-yl)methylsulfanyl]- 4-methyl-6-phenyl-1,6-dihydropyrimidin-5-yl}ethanone top

Crystal data top

C₂₁H₁₈Cl₂N₄OS₃	F(000) = 1048
M_r = 509.47	D_x = 1.492 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5976 reflections
a = 10.6123 (5) Å	θ = 2.4–27.5°
b = 18.7414 (6) Å	µ = 0.59 mm⁻¹
c = 12.4631 (9) Å	T = 300 K
β = 113.820 (1)°	Block, yellow
V = 2267.6 (2) Å³	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	4937 independent reflections
Radiation source: fine-focus sealed tube	3980 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
φ and ω scans	θ_max = 27.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000 or Sheldrick, 2001)	h = −13→13
T_min = 0.844, T_max = 0.892	k = −23→23
15492 measured reflections	l = −10→15

Refinement top

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.134	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0801P)² + 0.0525P] where P = (F_o² + 2F_c²)/3
4937 reflections	(Δ/σ)_max = 0.001
282 parameters	Δρ_max = 0.76 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₂₁H₁₈Cl₂N₄OS₃	V = 2267.6 (2) Å³
M_r = 509.47	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.6123 (5) Å	µ = 0.59 mm⁻¹
b = 18.7414 (6) Å	T = 300 K
c = 12.4631 (9) Å	0.30 × 0.20 × 0.20 mm
β = 113.820 (1)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	4937 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000 or Sheldrick, 2001)	3980 reflections with I > 2σ(I)
T_min = 0.844, T_max = 0.892	R_int = 0.043
15492 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.134	H-atom parameters constrained
S = 1.07	Δρ_max = 0.76 e Å⁻³
4937 reflections	Δρ_min = −0.26 e Å⁻³
282 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
C1	0.30256 (19)	0.89461 (10)	0.60611 (17)	0.0352 (4)
C2	0.3048 (2)	0.82610 (11)	0.5661 (2)	0.0465 (5)
H2	0.3766	0.7956	0.6091	0.056*
C3	0.2016 (3)	0.80212 (13)	0.4627 (2)	0.0585 (6)
H3	0.2047	0.7559	0.4368	0.070*
C4	0.0950 (3)	0.84651 (14)	0.3985 (2)	0.0559 (6)
H4	0.0253	0.8303	0.3295	0.067*
C5	0.0913 (2)	0.91513 (13)	0.4365 (2)	0.0513 (5)
H5	0.0194	0.9454	0.3928	0.062*
C6	0.1943 (2)	0.93915 (11)	0.53947 (19)	0.0436 (5)
H6	0.1912	0.9856	0.5645	0.052*
C7	0.41613 (19)	0.92033 (10)	0.71977 (17)	0.0341 (4)
H7	0.4727	0.8789	0.7580	0.041*
C8	0.36497 (19)	0.95276 (10)	0.80526 (16)	0.0330 (4)
C9	0.34482 (19)	1.02505 (10)	0.80124 (17)	0.0346 (4)
C10	0.48273 (19)	1.04236 (10)	0.70042 (16)	0.0351 (4)
C11	0.3459 (2)	0.90123 (11)	0.88574 (18)	0.0396 (5)
C12	0.3194 (3)	0.92329 (14)	0.9906 (2)	0.0549 (6)
H12A	0.2251	0.9378	0.9656	0.082*
H12B	0.3788	0.9624	1.0293	0.082*
H12C	0.3375	0.8838	1.0438	0.082*
C13	0.2709 (3)	1.06632 (12)	0.8610 (2)	0.0512 (6)
H13A	0.2031	1.0363	0.8711	0.077*
H13B	0.2263	1.1069	0.8140	0.077*
H13C	0.3358	1.0822	0.9363	0.077*
C14	0.6133 (2)	0.94307 (12)	0.66158 (19)	0.0425 (5)
H14A	0.6286	0.9759	0.6078	0.051*
H14B	0.5808	0.8984	0.6205	0.051*
C15	0.7465 (2)	0.93043 (11)	0.76409 (19)	0.0429 (5)
C16	0.8646 (2)	0.96685 (15)	0.7921 (2)	0.0635 (7)
H16	0.8723	1.0041	0.7458	0.076*
C17	0.9358 (2)	0.89425 (14)	0.9401 (2)	0.0561 (6)
C18	0.4988 (2)	1.18515 (11)	0.6571 (2)	0.0504 (6)
H18A	0.4788	1.1865	0.7265	0.061*
H18B	0.5626	1.2236	0.6635	0.061*
C19	0.3691 (2)	1.19778 (10)	0.5523 (2)	0.0444 (5)
C20	0.3491 (3)	1.24214 (12)	0.4621 (2)	0.0522 (6)
H20	0.4199	1.2709	0.4608	0.063*
C21	0.1427 (3)	1.19993 (12)	0.3961 (2)	0.0510 (6)
Cl1	1.04156 (7)	0.85525 (5)	1.06951 (7)	0.0834 (3)
Cl2	−0.02682 (7)	1.18481 (4)	0.30615 (7)	0.0712 (2)
N1	0.39481 (17)	1.06949 (8)	0.73819 (15)	0.0377 (4)
N2	0.50686 (16)	0.97250 (8)	0.69595 (14)	0.0356 (4)
N3	0.9741 (2)	0.94605 (14)	0.8934 (2)	0.0749 (7)
N4	0.2201 (2)	1.24354 (10)	0.37161 (18)	0.0582 (5)
O1	0.35742 (19)	0.83736 (9)	0.86936 (16)	0.0620 (5)
S1	0.76960 (6)	0.86607 (3)	0.86811 (6)	0.05590 (19)
S2	0.58141 (5)	1.10075 (3)	0.65412 (5)	0.04610 (17)
S3	0.21580 (6)	1.15434 (3)	0.52678 (6)	0.05366 (19)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0362 (10)	0.0342 (10)	0.0367 (11)	−0.0047 (7)	0.0164 (8)	−0.0023 (8)
C2	0.0535 (13)	0.0363 (11)	0.0498 (13)	0.0007 (9)	0.0211 (11)	−0.0046 (9)
C3	0.0711 (16)	0.0476 (13)	0.0580 (16)	−0.0150 (12)	0.0272 (13)	−0.0215 (12)
C4	0.0561 (14)	0.0641 (15)	0.0430 (14)	−0.0151 (12)	0.0153 (11)	−0.0146 (11)
C5	0.0451 (12)	0.0593 (14)	0.0423 (13)	−0.0012 (10)	0.0100 (10)	0.0003 (11)
C6	0.0421 (11)	0.0376 (11)	0.0459 (13)	0.0001 (8)	0.0122 (10)	−0.0056 (9)
C7	0.0332 (9)	0.0299 (9)	0.0367 (10)	0.0015 (7)	0.0115 (8)	0.0007 (8)
C8	0.0303 (9)	0.0353 (10)	0.0306 (10)	−0.0006 (7)	0.0094 (8)	−0.0009 (8)
C9	0.0315 (9)	0.0368 (10)	0.0317 (10)	−0.0006 (7)	0.0090 (8)	−0.0025 (8)
C10	0.0330 (9)	0.0386 (10)	0.0284 (10)	−0.0053 (7)	0.0069 (8)	0.0019 (8)
C11	0.0310 (10)	0.0444 (12)	0.0389 (11)	0.0000 (8)	0.0093 (8)	0.0055 (9)
C12	0.0532 (13)	0.0699 (16)	0.0433 (13)	0.0006 (11)	0.0213 (11)	0.0117 (11)
C13	0.0591 (14)	0.0440 (12)	0.0570 (15)	0.0039 (10)	0.0302 (12)	−0.0050 (10)
C14	0.0415 (11)	0.0483 (12)	0.0407 (12)	−0.0017 (9)	0.0198 (9)	−0.0052 (9)
C15	0.0399 (11)	0.0490 (12)	0.0439 (12)	0.0029 (9)	0.0211 (10)	−0.0003 (9)
C16	0.0407 (12)	0.0721 (17)	0.0715 (17)	−0.0041 (11)	0.0160 (12)	0.0236 (14)
C17	0.0439 (12)	0.0660 (16)	0.0560 (15)	0.0077 (11)	0.0177 (11)	0.0118 (12)
C18	0.0590 (14)	0.0349 (11)	0.0551 (14)	−0.0140 (9)	0.0206 (11)	−0.0030 (10)
C19	0.0520 (12)	0.0313 (10)	0.0520 (13)	−0.0038 (8)	0.0231 (10)	0.0000 (9)
C20	0.0624 (15)	0.0351 (11)	0.0632 (16)	−0.0009 (10)	0.0296 (13)	0.0074 (10)
C21	0.0603 (14)	0.0382 (11)	0.0506 (14)	0.0060 (10)	0.0184 (11)	0.0074 (10)
Cl1	0.0588 (4)	0.1075 (6)	0.0750 (5)	0.0151 (4)	0.0177 (4)	0.0418 (4)
Cl2	0.0631 (4)	0.0636 (4)	0.0670 (4)	0.0024 (3)	0.0057 (3)	0.0088 (3)
N1	0.0402 (9)	0.0326 (8)	0.0374 (9)	0.0000 (7)	0.0126 (7)	0.0006 (7)
N2	0.0346 (9)	0.0352 (8)	0.0381 (9)	−0.0030 (6)	0.0158 (7)	−0.0025 (7)
N3	0.0450 (12)	0.0864 (17)	0.0816 (17)	−0.0085 (11)	0.0135 (12)	0.0285 (14)
N4	0.0705 (14)	0.0437 (11)	0.0603 (14)	0.0076 (10)	0.0264 (11)	0.0142 (9)
O1	0.0827 (12)	0.0392 (9)	0.0756 (13)	0.0039 (8)	0.0438 (10)	0.0130 (8)
S1	0.0509 (3)	0.0574 (4)	0.0604 (4)	−0.0046 (3)	0.0236 (3)	0.0117 (3)
S2	0.0416 (3)	0.0460 (3)	0.0490 (3)	−0.0067 (2)	0.0164 (2)	0.0080 (2)
S3	0.0523 (3)	0.0485 (3)	0.0548 (4)	−0.0068 (2)	0.0160 (3)	0.0128 (3)

Geometric parameters (Å, º) top

C1—C2	1.381 (3)	C12—H12C	0.9600
C1—C6	1.391 (3)	C13—H13A	0.9600
C1—C7	1.521 (3)	C13—H13B	0.9600
C2—C3	1.387 (3)	C13—H13C	0.9600
C2—H2	0.9300	C14—N2	1.468 (3)
C3—C4	1.372 (4)	C14—C15	1.492 (3)
C3—H3	0.9300	C14—H14A	0.9700
C4—C5	1.376 (3)	C14—H14B	0.9700
C4—H4	0.9300	C15—C16	1.344 (3)
C5—C6	1.382 (3)	C15—S1	1.714 (2)
C5—H5	0.9300	C16—N3	1.382 (3)
C6—H6	0.9300	C16—H16	0.9300
C7—N2	1.484 (2)	C17—N3	1.280 (3)
C7—C8	1.506 (3)	C17—S1	1.708 (3)
C7—H7	0.9800	C17—Cl1	1.712 (3)
C8—C9	1.369 (3)	C18—C19	1.485 (3)
C8—C11	1.464 (3)	C18—S2	1.816 (2)
C9—N1	1.389 (2)	C18—H18A	0.9700
C9—C13	1.497 (3)	C18—H18B	0.9700
C10—N1	1.306 (3)	C19—C20	1.344 (3)
C10—N2	1.340 (3)	C19—S3	1.730 (2)
C10—S2	1.7649 (19)	C20—N4	1.378 (3)
C11—O1	1.229 (3)	C20—H20	0.9300
C11—C12	1.501 (3)	C21—N4	1.280 (3)
C12—H12A	0.9600	C21—Cl2	1.716 (3)
C12—H12B	0.9600	C21—S3	1.722 (2)

C2—C1—C6	118.21 (19)	H13A—C13—H13B	109.5
C2—C1—C7	120.55 (18)	C9—C13—H13C	109.5
C6—C1—C7	121.24 (17)	H13A—C13—H13C	109.5
C1—C2—C3	121.0 (2)	H13B—C13—H13C	109.5
C1—C2—H2	119.5	N2—C14—C15	112.58 (17)
C3—C2—H2	119.5	N2—C14—H14A	109.1
C4—C3—C2	120.1 (2)	C15—C14—H14A	109.1
C4—C3—H3	120.0	N2—C14—H14B	109.1
C2—C3—H3	120.0	C15—C14—H14B	109.1
C3—C4—C5	119.8 (2)	H14A—C14—H14B	107.8
C3—C4—H4	120.1	C16—C15—C14	127.1 (2)
C5—C4—H4	120.1	C16—C15—S1	109.09 (18)
C4—C5—C6	120.1 (2)	C14—C15—S1	123.79 (16)
C4—C5—H5	119.9	C15—C16—N3	116.5 (2)
C6—C5—H5	119.9	C15—C16—H16	121.8
C5—C6—C1	120.8 (2)	N3—C16—H16	121.8
C5—C6—H6	119.6	N3—C17—S1	116.4 (2)
C1—C6—H6	119.6	N3—C17—Cl1	123.0 (2)
N2—C7—C8	108.91 (15)	S1—C17—Cl1	120.53 (15)
N2—C7—C1	110.90 (15)	C19—C18—S2	113.85 (16)
C8—C7—C1	114.23 (15)	C19—C18—H18A	108.8
N2—C7—H7	107.5	S2—C18—H18A	108.8
C8—C7—H7	107.5	C19—C18—H18B	108.8
C1—C7—H7	107.5	S2—C18—H18B	108.8
C9—C8—C11	127.94 (18)	H18A—C18—H18B	107.7
C9—C8—C7	117.97 (17)	C20—C19—C18	127.7 (2)
C11—C8—C7	114.07 (16)	C20—C19—S3	108.54 (18)
C8—C9—N1	121.62 (17)	C18—C19—S3	123.73 (16)
C8—C9—C13	126.75 (19)	C19—C20—N4	117.7 (2)
N1—C9—C13	111.63 (17)	C19—C20—H20	121.1
N1—C10—N2	124.88 (17)	N4—C20—H20	121.1
N1—C10—S2	118.76 (15)	N4—C21—Cl2	123.68 (19)
N2—C10—S2	116.34 (15)	N4—C21—S3	117.07 (19)
O1—C11—C8	118.55 (19)	Cl2—C21—S3	119.25 (14)
O1—C11—C12	118.6 (2)	C10—N1—C9	117.53 (16)
C8—C11—C12	122.74 (19)	C10—N2—C14	124.19 (17)
C11—C12—H12A	109.5	C10—N2—C7	119.04 (15)
C11—C12—H12B	109.5	C14—N2—C7	116.66 (16)
H12A—C12—H12B	109.5	C17—N3—C16	109.0 (2)
C11—C12—H12C	109.5	C21—N4—C20	108.3 (2)
H12A—C12—H12C	109.5	C17—S1—C15	88.97 (11)
H12B—C12—H12C	109.5	C10—S2—C18	100.26 (10)
C9—C13—H13A	109.5	C21—S3—C19	88.34 (12)
C9—C13—H13B	109.5

C6—C1—C2—C3	−0.4 (3)	N2—C10—N1—C9	14.7 (3)
C7—C1—C2—C3	179.9 (2)	S2—C10—N1—C9	−163.91 (14)
C1—C2—C3—C4	−0.1 (4)	C8—C9—N1—C10	−12.2 (3)
C2—C3—C4—C5	0.6 (4)	C13—C9—N1—C10	167.42 (18)
C3—C4—C5—C6	−0.4 (4)	N1—C10—N2—C14	−175.22 (18)
C4—C5—C6—C1	−0.1 (4)	S2—C10—N2—C14	3.4 (2)
C2—C1—C6—C5	0.5 (3)	N1—C10—N2—C7	8.7 (3)
C7—C1—C6—C5	−179.7 (2)	S2—C10—N2—C7	−172.67 (13)
C2—C1—C7—N2	108.2 (2)	C15—C14—N2—C10	92.6 (2)
C6—C1—C7—N2	−71.5 (2)	C15—C14—N2—C7	−91.3 (2)
C2—C1—C7—C8	−128.2 (2)	C8—C7—N2—C10	−30.7 (2)
C6—C1—C7—C8	52.1 (2)	C1—C7—N2—C10	95.8 (2)
N2—C7—C8—C9	32.2 (2)	C8—C7—N2—C14	152.93 (16)
C1—C7—C8—C9	−92.4 (2)	C1—C7—N2—C14	−80.5 (2)
N2—C7—C8—C11	−146.46 (16)	S1—C17—N3—C16	0.4 (3)
C1—C7—C8—C11	88.9 (2)	Cl1—C17—N3—C16	−178.2 (2)
C11—C8—C9—N1	165.72 (18)	C15—C16—N3—C17	−0.2 (4)
C7—C8—C9—N1	−12.7 (3)	Cl2—C21—N4—C20	−179.69 (18)
C11—C8—C9—C13	−13.8 (3)	S3—C21—N4—C20	0.0 (3)
C7—C8—C9—C13	167.71 (19)	C19—C20—N4—C21	0.8 (3)
C9—C8—C11—O1	173.7 (2)	N3—C17—S1—C15	−0.4 (2)
C7—C8—C11—O1	−7.8 (3)	Cl1—C17—S1—C15	178.23 (18)
C9—C8—C11—C12	−9.3 (3)	C16—C15—S1—C17	0.2 (2)
C7—C8—C11—C12	169.16 (18)	C14—C15—S1—C17	−178.51 (19)
N2—C14—C15—C16	−109.7 (3)	N1—C10—S2—C18	−8.43 (18)
N2—C14—C15—S1	68.8 (2)	N2—C10—S2—C18	172.88 (16)
C14—C15—C16—N3	178.6 (2)	C19—C18—S2—C10	−80.61 (18)
S1—C15—C16—N3	−0.1 (3)	N4—C21—S3—C19	−0.6 (2)
S2—C18—C19—C20	−105.1 (2)	Cl2—C21—S3—C19	179.16 (15)
S2—C18—C19—S3	73.8 (2)	C20—C19—S3—C21	0.92 (18)
C18—C19—C20—N4	177.9 (2)	C18—C19—S3—C21	−178.2 (2)
S3—C19—C20—N4	−1.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18A···N1	0.97	2.39	2.799 (3)	105
C14—H14A···S2	0.97	2.51	2.972 (2)	109
C7—H7···O1	0.98	2.32	2.687 (3)	101
C18—H18B···O1ⁱ	0.97	2.39	3.314 (3)	159
C12—H12A···N3ⁱⁱ	0.96	2.45	3.390 (3)	167

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₈Cl₂N₄OS₃
M_r	509.47
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	300
a, b, c (Å)	10.6123 (5), 18.7414 (6), 12.4631 (9)
β (°)	113.820 (1)
V (Å³)	2267.6 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.59
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2000 or Sheldrick, 2001)
T_min, T_max	0.844, 0.892
No. of measured, independent and observed [I > 2σ(I)] reflections	15492, 4937, 3980
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.134, 1.07
No. of reflections	4937
No. of parameters	282
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.76, −0.26

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.