5-Benzyl­amino-6-phenyl-2-propyl­sulfanylthia­zolo[5,4-d]pyrimidin-7(6H)-one

Huang, N.-Y.; Yuan, J.-Z.; Xu, R.-J.; Ding, M.-W.; He, H.-W.

doi:10.1107/S1600536805039929

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5-Benzylamino-6-phenyl-2-propylsulfanylthiazolo[5,4-d]pyrimidin-7(6H)-one

N.-Y. Huang, J.-Z. Yuan, R.-J. Xu, M.-W. Ding and H.-W. He

In the title compound, C₂₁H₂₀N₄OS₂, the two rings of the fused thiazolo[5,4-d]pyrimidine system are almost coplanar. In the crystal structure, hydrogen-bonded tetramers are formed via N—H

N hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805039929/su6249sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805039929/su6249Isup2.hkl Contains datablock I

CCDC reference: 296676

checkCIF report

Key indicators

Single-crystal X-ray study
T = 292 K
Mean (C-C) = 0.007 Å
Disorder in main residue
R factor = 0.066
wR factor = 0.183
Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       4.20 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.72 Ratio
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for        C19
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for       C19'

Alert level C
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         S1
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         S2
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C2
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C4
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        S2'
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C6
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C18
PLAT301_ALERT_3_C Main Residue  Disorder .........................      12.00 Perc.
PLAT322_ALERT_2_C Check Hybridisation of  S1     in Main Residue .          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7

   0 ALERT level A = In general: serious problem
   4 ALERT level B = Potentially serious problem
  10 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
  11 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

The thiazolo[5,4-d]pyrimidines are purine analogue derivatives and they have potentially useful biological properties (Khairy or El-Bayouki et al., 1988). In recent years we have been engaged in the synthesis of derivatives of various heterocycles via the aza-Wittig reaction (Ding, Yang & Zhu, 2004; Ding, Chen & Huang, 2004). The title compound, (I), may be used as a new precursor for obtaining bioactive molecules and we report here on the X-ray crystallographic analysis of this compound.

The molecular structure of the title compound is shown in Fig. 1, and selected bond distances and anges are given in Table 1. A l l the ring atoms in the thiazolo[5,4-d]pyrimidine system are essentially coplanar. The n-propylthio group is disordered [occupancies 0.583 (6)/0.417 (6); normal/primed atoms].

In the crystal structure of (I), symmetry-related molecules are linked via N—H···N hydrogen bonds to form tetramers. Details are given in Table 2 and Fig. 2.

Experimental top

Compound (I) was prepared by adding benzyl amine (0.22 g) to a solution of ethyl 5-[(phenylimino)methyleneamino]-2-(propylthio)thiazole-4-carboxylate (2 mmol) in dry dichloromethane (10 ml). The solution was stirred for 2 h at 298 K. The solvent was then removed and anhydrous ethanol (10 ml), containing several drops of EtONa in EtOH, was added. The mixture was stirred for 6 h at room temperature. The solution was then concentrated under reduced pressure and the residue was recrystallized from ethanol to give compound (I), in a yield of 85% (m.p. 460 K). Suitable crystals were obtained by vapor diffusion of ethanol and dichloromethane at room temperature. ¹HNMR (CDCl₃, 400 MHz): 7.17–7.58 (m, 10H, Ph—H), 4.57–4.59 (m, 3H, N1—H, C7—H), 3.26–3.3(t, 2H, C19—H), 1.78–1.82 (m, 2H, C20—H), 1.03–1.06 (t, 3H, C21—H).

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, 2001); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. View of the molecular structure of (I), showing the atom labeling scheme and displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. A partial view of the crystal packing of (I), showing the formation of an N—H···N hydrogen-bonded tetramer. Hydrogen bonds are shown as dashed lines and atoms labelled a, b and c correspond to symmetry operations (y, 3/2 − x, 3/2 − z), (3/2 − x, 3/2 − y, z) and (3/2 − y, x, 3/2 − z), respectively.

5-Benzylamino-6-phenyl-2-propylsulfanylthiazolo[5,4-d]pyrimidin-7(6H)-one top

Crystal data top

C₂₁H₂₀N₄OS₂	D_x = 1.281 Mg m⁻³
M_r = 408.53	Melting point: 460 K
Tetragonal, P4₂/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 4bc	Cell parameters from 2882 reflections
a = 23.3140 (6) Å	θ = 2.5–16.9°
c = 7.7925 (4) Å	µ = 0.27 mm⁻¹
V = 4235.6 (3) Å³	T = 292 K
Z = 8	Plate, colorless
F(000) = 1712	0.30 × 0.20 × 0.06 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	2138 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.080
Graphite monochromator	θ_max = 25.0°, θ_min = 1.8°
ϕ and ω scans	h = −27→27
29639 measured reflections	k = −27→27
3737 independent reflections	l = −9→9

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.183	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0722P)² + 1.9388P] where P = (F_o² + 2F_c²)/3
3737 reflections	(Δ/σ)_max < 0.001
268 parameters	Δρ_max = 0.29 e Å⁻³
6 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₂₁H₂₀N₄OS₂	Z = 8
M_r = 408.53	Mo Kα radiation
Tetragonal, P4₂/n	µ = 0.27 mm⁻¹
a = 23.3140 (6) Å	T = 292 K
c = 7.7925 (4) Å	0.30 × 0.20 × 0.06 mm
V = 4235.6 (3) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	2138 reflections with I > 2σ(I)
29639 measured reflections	R_int = 0.080
3737 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	6 restraints
wR(F²) = 0.183	H-atom parameters constrained
S = 1.04	Δρ_max = 0.29 e Å⁻³
3737 reflections	Δρ_min = −0.30 e Å⁻³
268 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.55334 (5)	0.56594 (5)	1.10174 (16)	0.0979 (5)
S2	0.6239 (4)	0.4500 (3)	1.0534 (9)	0.130 (2)	0.583 (6)
O1	0.65866 (12)	0.62054 (12)	0.5825 (3)	0.0893 (11)
N1	0.52552 (12)	0.75071 (12)	0.7841 (4)	0.0721 (11)
N2	0.53566 (12)	0.66679 (13)	0.9338 (4)	0.0667 (11)
N3	0.59301 (11)	0.68446 (12)	0.6859 (4)	0.0601 (10)
N4	0.62944 (14)	0.54410 (14)	0.8690 (5)	0.0827 (14)
C1	0.3984 (2)	0.7227 (2)	1.0339 (8)	0.123 (3)
C2	0.3456 (3)	0.6969 (3)	1.0269 (12)	0.150 (3)
C3	0.3192 (3)	0.6915 (3)	0.8739 (13)	0.140 (4)
C4	0.3446 (3)	0.7092 (3)	0.7279 (12)	0.151 (4)
C5	0.3998 (2)	0.7352 (2)	0.7347 (9)	0.126 (3)
C6	0.42588 (17)	0.74259 (16)	0.8878 (7)	0.0827 (18)
C7	0.48311 (15)	0.77110 (16)	0.9041 (6)	0.0800 (14)
C8	0.61077 (15)	0.72495 (15)	0.5556 (4)	0.0593 (12)
C9	0.58091 (18)	0.73072 (19)	0.4047 (5)	0.0827 (17)
C10	0.6004 (2)	0.7695 (2)	0.2832 (5)	0.0887 (17)
C11	0.6487 (2)	0.80113 (18)	0.3115 (6)	0.0830 (17)
C12	0.67853 (18)	0.79437 (17)	0.4603 (5)	0.0770 (16)
C13	0.65939 (16)	0.75657 (15)	0.5830 (4)	0.0663 (14)
C14	0.55141 (14)	0.69969 (15)	0.8061 (5)	0.0603 (12)
C15	0.62214 (16)	0.63135 (16)	0.6904 (5)	0.0660 (12)
C16	0.60515 (15)	0.59689 (15)	0.8311 (5)	0.0647 (12)
C17	0.56412 (15)	0.61624 (16)	0.9402 (5)	0.0660 (14)
C18	0.60648 (19)	0.52334 (18)	1.0048 (7)	0.0940 (19)
C19	0.5727 (4)	0.4319 (4)	1.2132 (11)	0.111 (4)	0.583 (6)
C20	0.5871 (6)	0.4350 (9)	1.3978 (13)	0.189 (7)	0.583 (6)
C21	0.545 (4)	0.418 (11)	1.535 (4)	0.249 (7)	0.583 (6)
C20'	0.5505 (7)	0.4243 (10)	1.326 (3)	0.189 (7)	0.417 (6)
C21'	0.548 (5)	0.418 (15)	1.519 (5)	0.249 (7)	0.417 (6)
S2'	0.6322 (6)	0.4655 (4)	1.1230 (11)	0.130 (2)	0.417 (6)
C19'	0.6035 (5)	0.4587 (6)	1.3245 (18)	0.111 (4)	0.417 (6)
H2	0.32820	0.68330	1.12640	0.1800*
H3	0.28280	0.67520	0.86890	0.1680*
H4	0.32610	0.70450	0.62310	0.1810*
H1	0.41630	0.72690	1.13980	0.1470*
H1A	0.53440	0.77150	0.69700	0.0860*
H9	0.54820	0.70900	0.38440	0.0990*
H10	0.58020	0.77410	0.18110	0.1060*
H11	0.66120	0.82720	0.22930	0.1000*
H12	0.71190	0.81530	0.47890	0.0920*
H13	0.67960	0.75250	0.68520	0.0790*
H19A	0.53960	0.45640	1.19500	0.1280*	0.583 (6)
H19B	0.56040	0.39290	1.19020	0.1280*	0.583 (6)
H20A	0.59790	0.47440	1.42160	0.2260*	0.583 (6)
H20B	0.62120	0.41190	1.41480	0.2260*	0.583 (6)
H21A	0.50630	0.42580	1.49600	0.3730*	0.583 (6)
H21B	0.55220	0.43850	1.63820	0.3730*	0.583 (6)
H21C	0.54810	0.37720	1.55670	0.3730*	0.583 (6)
H5	0.41780	0.74710	0.63430	0.1510*
H7A	0.47820	0.81200	0.88780	0.0960*
H7B	0.49740	0.76520	1.01970	0.0960*
H19C	0.63160	0.44080	1.39920	0.1280*	0.417 (6)
H19D	0.59530	0.49650	1.37000	0.1280*	0.417 (6)
H20C	0.55480	0.38790	1.26670	0.2260*	0.417 (6)
H20D	0.51780	0.44510	1.28020	0.2260*	0.417 (6)
H21D	0.56390	0.38120	1.55050	0.3730*	0.417 (6)
H21E	0.50920	0.42030	1.55680	0.3730*	0.417 (6)
H21F	0.57040	0.44780	1.57130	0.3730*	0.417 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0909 (8)	0.0975 (9)	0.1053 (9)	0.0174 (6)	0.0431 (7)	0.0436 (7)
S2	0.157 (3)	0.087 (3)	0.146 (5)	0.043 (3)	0.060 (4)	0.054 (3)
O1	0.100 (2)	0.0892 (19)	0.0787 (18)	0.0291 (16)	0.0396 (17)	0.0122 (15)
N1	0.0606 (18)	0.0596 (19)	0.096 (2)	0.0032 (15)	0.0241 (17)	0.0089 (17)
N2	0.0581 (18)	0.0651 (19)	0.077 (2)	0.0025 (15)	0.0203 (15)	0.0084 (17)
N3	0.0549 (17)	0.0623 (18)	0.0632 (18)	0.0061 (14)	0.0118 (15)	0.0108 (15)
N4	0.081 (2)	0.071 (2)	0.096 (3)	0.0162 (18)	0.029 (2)	0.0224 (19)
C1	0.096 (4)	0.115 (4)	0.157 (5)	−0.028 (3)	0.048 (4)	−0.017 (4)
C2	0.109 (5)	0.154 (6)	0.187 (7)	−0.045 (4)	0.055 (5)	−0.017 (5)
C3	0.074 (4)	0.109 (5)	0.237 (9)	−0.018 (3)	0.003 (5)	0.021 (6)
C4	0.110 (5)	0.115 (5)	0.228 (8)	−0.023 (4)	−0.050 (5)	0.061 (5)
C5	0.103 (4)	0.104 (4)	0.172 (6)	−0.019 (3)	−0.033 (4)	0.054 (4)
C6	0.059 (3)	0.055 (2)	0.134 (4)	0.0064 (19)	0.020 (3)	0.013 (3)
C7	0.061 (2)	0.060 (2)	0.119 (3)	0.0038 (19)	0.021 (2)	−0.002 (2)
C8	0.057 (2)	0.066 (2)	0.055 (2)	0.0073 (18)	0.0031 (18)	0.0075 (18)
C9	0.072 (3)	0.095 (3)	0.081 (3)	−0.004 (2)	−0.009 (2)	0.010 (2)
C10	0.098 (3)	0.110 (3)	0.058 (3)	0.008 (3)	−0.011 (2)	0.021 (2)
C11	0.098 (3)	0.083 (3)	0.068 (3)	0.005 (3)	0.014 (3)	0.021 (2)
C12	0.086 (3)	0.084 (3)	0.061 (2)	−0.008 (2)	0.007 (2)	0.013 (2)
C13	0.075 (3)	0.072 (2)	0.052 (2)	−0.003 (2)	0.0037 (19)	0.0115 (19)
C14	0.050 (2)	0.055 (2)	0.076 (2)	−0.0035 (17)	0.0093 (19)	0.0007 (19)
C15	0.067 (2)	0.068 (2)	0.063 (2)	0.009 (2)	0.011 (2)	0.0073 (19)
C16	0.062 (2)	0.060 (2)	0.072 (2)	0.0069 (18)	0.0174 (19)	0.0127 (19)
C17	0.056 (2)	0.068 (2)	0.074 (3)	−0.0022 (19)	0.0142 (19)	0.012 (2)
C18	0.085 (3)	0.084 (3)	0.113 (4)	0.017 (2)	0.029 (3)	0.038 (3)
C19	0.109 (6)	0.090 (5)	0.135 (8)	−0.011 (4)	−0.011 (5)	0.046 (5)
C20	0.111 (9)	0.325 (17)	0.130 (10)	−0.059 (11)	0.005 (7)	−0.047 (10)
C21	0.286 (16)	0.311 (13)	0.150 (7)	0.010 (17)	0.105 (12)	0.050 (19)
C20'	0.111 (9)	0.325 (17)	0.130 (10)	−0.059 (11)	0.005 (7)	−0.047 (10)
C21'	0.286 (16)	0.311 (13)	0.150 (7)	0.010 (17)	0.105 (12)	0.050 (19)
S2'	0.157 (3)	0.087 (3)	0.146 (5)	0.043 (3)	0.060 (4)	0.054 (3)
C19'	0.109 (6)	0.090 (5)	0.135 (8)	−0.011 (4)	−0.011 (5)	0.046 (5)

Geometric parameters (Å, º) top

S1—C17	1.739 (4)	C16—C17	1.357 (5)
S1—C18	1.758 (5)	C19—C20	1.479 (14)
S2—C18	1.798 (8)	C19'—C20'	1.47 (2)
S2—C19	1.776 (12)	C20—C21	1.51 (8)
S2'—C19'	1.714 (17)	C20'—C21'	1.51 (5)
S2'—C18	1.740 (11)	C1—H1	0.9300
O1—C15	1.223 (5)	C2—H2	0.9300
N1—C7	1.442 (5)	C3—H3	0.9300
N1—C14	1.345 (4)	C4—H4	0.9300
N2—C17	1.353 (5)	C5—H5	0.9300
N2—C14	1.309 (5)	C7—H7A	0.9700
N3—C15	1.413 (5)	C7—H7B	0.9700
N3—C8	1.447 (4)	C9—H9	0.9300
N3—C14	1.394 (5)	C10—H10	0.9300
N4—C16	1.387 (5)	C11—H11	0.9300
N4—C18	1.281 (6)	C12—H12	0.9300
N1—H1A	0.8600	C13—H13	0.9300
C1—C6	1.386 (8)	C19—H19A	0.9700
C1—C2	1.371 (8)	C19—H19B	0.9700
C2—C3	1.348 (13)	C19'—H19D	0.9700
C3—C4	1.347 (13)	C19'—H19C	0.9700
C4—C5	1.424 (8)	C20—H20B	0.9700
C5—C6	1.350 (8)	C20—H20A	0.9700
C6—C7	1.496 (5)	C20'—H20C	0.9700
C8—C13	1.369 (5)	C20'—H20D	0.9700
C8—C9	1.373 (5)	C21—H21B	0.9500
C9—C10	1.386 (6)	C21—H21C	0.9700
C10—C11	1.364 (6)	C21—H21A	0.9700
C11—C12	1.361 (6)	C21'—H21D	0.9700
C12—C13	1.375 (5)	C21'—H21E	0.9500
C15—C16	1.416 (5)	C21'—H21F	0.9600

S1···N4	2.588 (4)	C8···H11^iv	3.0400
S1···C21ⁱ	3.66 (7)	C9···H11^iv	2.8800
S2···C3ⁱⁱ	3.601 (10)	C9···H1A	2.7000
S2···C2ⁱⁱ	3.553 (10)	C10···H11^iv	3.0400
S1···H19D	2.8200	C13···H1A	3.0700
S1···H19A	2.6700	C17···H19Bⁱⁱ	3.0800
S1···H21Eⁱ	3.0500	C17···H20Dⁱⁱ	2.9400
S1···H21Bⁱ	3.1900	C19'···H7A^ix	3.0200
O1···N4	2.937 (4)	C20···H7A^ix	3.0600
O1···C13	3.172 (4)	H1···H7B	2.2900
O1···N1ⁱⁱⁱ	3.233 (4)	H1A···C13	3.0700
O1···C10^iv	3.339 (5)	H1A···N4^v	2.3800
O1···C11^iv	3.277 (5)	H1A···C9	2.7000
O1···C13ⁱⁱⁱ	3.394 (4)	H1A···C8	2.3600
O1···H10^iv	2.7500	H2···C4^x	2.9600
O1···H11^iv	2.6300	H2···C5^x	3.0300
N1···C9	3.260 (5)	H5···N1	2.7700
N1···O1^v	3.233 (4)	H7A···N4^v	2.8700
N1···N4^v	3.069 (4)	H7A···C19'^viii	3.0200
N2···C6	3.131 (5)	H7A···H19C^viii	2.2900
N4···S1	2.588 (4)	H7A···C20^viii	3.0600
N4···O1	2.937 (4)	H7A···H20A^viii	2.5700
N4···N1ⁱⁱⁱ	3.069 (4)	H7B···H10^xi	2.3100
N1···H5	2.7700	H7B···N2	2.5500
N2···H7B	2.5500	H7B···H1	2.2900
N2···H19Bⁱⁱ	2.8100	H10···O1^vi	2.7500
N2···H20Cⁱⁱ	2.9200	H10···H7B^xii	2.3100
N4···H1Aⁱⁱⁱ	2.3800	H11···C8^vi	3.0400
N4···H7Aⁱⁱⁱ	2.8700	H11···C9^vi	2.8800
C2···S2ⁱⁱ	3.553 (10)	H11···O1^vi	2.6300
C3···S2ⁱⁱ	3.601 (10)	H11···C10^vi	3.0400
C6···N2	3.131 (5)	H13···H13ⁱⁱⁱ	2.5300
C9···N1	3.260 (5)	H13···H13^v	2.5300
C10···O1^vi	3.339 (5)	H19A···H21A	2.5700
C11···O1^vi	3.277 (5)	H19A···S1	2.6700
C12···C16^v	3.428 (5)	H19B···C17ⁱⁱ	3.0800
C12···C15^v	3.522 (6)	H19B···N2ⁱⁱ	2.8100
C13···O1^v	3.394 (4)	H19C···H21D	2.4100
C13···C15^v	3.397 (5)	H19C···C7^ix	2.9100
C13···O1	3.172 (4)	H19C···H7A^ix	2.2900
C15···C13ⁱⁱⁱ	3.397 (5)	H19C···H21F	1.9600
C15···C12ⁱⁱⁱ	3.522 (6)	H19D···S1	2.8200
C16···C12ⁱⁱⁱ	3.428 (5)	H19D···H21F	2.0200
C17···C20'ⁱⁱ	3.51 (2)	H20A···H7A^ix	2.5700
C17···C19ⁱⁱ	3.587 (10)	H20C···N2ⁱⁱ	2.9200
C19···C17ⁱⁱ	3.587 (10)	H20C···C5ⁱⁱ	3.0600
C20'···C17ⁱⁱ	3.51 (2)	H20D···C17ⁱⁱ	2.9400
C21···S1ⁱ	3.66 (7)	H21A···H19A	2.5700
C4···H2^vii	2.9600	H21B···S1ⁱ	3.1900
C5···H20Cⁱⁱ	3.0600	H21D···H19C	2.4100
C5···H2^vii	3.0300	H21E···S1ⁱ	3.0500
C7···H19C^viii	2.9100	H21F···H19C	1.9600
C8···H1A	2.3600	H21F···H19D	2.0200

C17—S1—C18	88.2 (2)	C2—C3—H3	119.00
C18—S2—C19	102.8 (5)	C4—C3—H3	119.00
C18—S2'—C19'	115.0 (8)	C3—C4—H4	120.00
C7—N1—C14	121.1 (3)	C5—C4—H4	120.00
C14—N2—C17	113.6 (3)	C4—C5—H5	120.00
C8—N3—C14	120.3 (3)	C6—C5—H5	120.00
C8—N3—C15	116.9 (3)	N1—C7—H7A	109.00
C14—N3—C15	122.8 (3)	N1—C7—H7B	109.00
C16—N4—C18	109.9 (3)	C6—C7—H7A	109.00
C7—N1—H1A	119.00	C6—C7—H7B	109.00
C14—N1—H1A	119.00	H7A—C7—H7B	108.00
C2—C1—C6	121.9 (6)	C8—C9—H9	121.00
C1—C2—C3	119.1 (8)	C10—C9—H9	121.00
C2—C3—C4	121.2 (7)	C9—C10—H10	120.00
C3—C4—C5	119.8 (8)	C11—C10—H10	120.00
C4—C5—C6	119.6 (6)	C10—C11—H11	120.00
C5—C6—C7	122.2 (5)	C12—C11—H11	120.00
C1—C6—C7	119.4 (5)	C11—C12—H12	120.00
C1—C6—C5	118.4 (4)	C13—C12—H12	120.00
N1—C7—C6	114.2 (3)	C8—C13—H13	120.00
N3—C8—C9	121.3 (3)	C12—C13—H13	120.00
C9—C8—C13	120.0 (3)	S2—C19—H19A	107.00
N3—C8—C13	118.6 (3)	S2—C19—H19B	107.00
C8—C9—C10	118.9 (4)	C20—C19—H19A	107.00
C9—C10—C11	120.9 (4)	C20—C19—H19B	107.00
C10—C11—C12	119.8 (4)	H19A—C19—H19B	107.00
C11—C12—C13	120.1 (4)	H19C—C19'—H19D	108.00
C8—C13—C12	120.4 (3)	S2'—C19'—H19C	109.00
N2—C14—N3	123.8 (3)	S2'—C19'—H19D	109.00
N1—C14—N3	116.9 (3)	C20'—C19'—H19C	109.00
N1—C14—N2	119.3 (3)	C20'—C19'—H19D	109.00
O1—C15—N3	119.9 (3)	C21—C20—H20A	106.00
O1—C15—C16	127.6 (3)	C21—C20—H20B	107.00
N3—C15—C16	112.5 (3)	C19—C20—H20B	107.00
N4—C16—C15	123.7 (3)	C19—C20—H20A	107.00
C15—C16—C17	119.6 (3)	H20A—C20—H20B	107.00
N4—C16—C17	116.7 (3)	C19'—C20'—H20C	113.00
S1—C17—C16	109.4 (3)	C19'—C20'—H20D	113.00
N2—C17—C16	127.7 (4)	H20C—C20'—H20D	110.00
S1—C17—N2	122.9 (3)	C21'—C20'—H20D	113.00
S1—C18—S2'	117.0 (5)	C21'—C20'—H20C	113.00
S1—C18—N4	115.9 (3)	C20—C21—H21C	110.00
S2'—C18—N4	125.9 (5)	C20—C21—H21B	111.00
S1—C18—S2	127.3 (4)	H21B—C21—H21C	109.00
S2—C18—N4	116.0 (4)	H21A—C21—H21B	110.00
S2—C19—C20	121.2 (8)	H21A—C21—H21C	108.00
S2'—C19'—C20'	112.7 (13)	C20—C21—H21A	110.00
C19—C20—C21	122 (3)	C20'—C21'—H21D	109.00
C19'—C20'—C21'	95 (8)	C20'—C21'—H21E	110.00
C2—C1—H1	119.00	C20'—C21'—H21F	109.00
C6—C1—H1	119.00	H21D—C21'—H21E	110.00
C1—C2—H2	121.00	H21D—C21'—H21F	109.00
C3—C2—H2	120.00	H21E—C21'—H21F	110.00

C18—S1—C17—C16	0.3 (3)	C16—N4—C18—S2	170.0 (4)
C17—S1—C18—N4	0.1 (4)	C2—C1—C6—C5	−1.1 (7)
C17—S1—C18—S2	−169.1 (5)	C6—C1—C2—C3	−1.1 (9)
C18—S1—C17—N2	−178.2 (3)	C2—C1—C6—C7	179.2 (5)
C18—S2—C19—C20	−96.5 (12)	C1—C2—C3—C4	2.3 (11)
C19—S2—C18—S1	2.4 (7)	C2—C3—C4—C5	−1.3 (11)
C19—S2—C18—N4	−166.7 (5)	C3—C4—C5—C6	−0.9 (9)
C7—N1—C14—N2	3.5 (5)	C4—C5—C6—C1	2.0 (7)
C14—N1—C7—C6	−75.6 (5)	C4—C5—C6—C7	−178.2 (5)
C7—N1—C14—N3	−178.2 (3)	C5—C6—C7—N1	−47.1 (5)
C14—N2—C17—C16	−0.7 (5)	C1—C6—C7—N1	132.6 (4)
C14—N2—C17—S1	177.5 (3)	N3—C8—C13—C12	178.3 (3)
C17—N2—C14—N1	178.8 (3)	C9—C8—C13—C12	0.2 (6)
C17—N2—C14—N3	0.7 (5)	C13—C8—C9—C10	−1.0 (6)
C14—N3—C8—C13	97.0 (4)	N3—C8—C9—C10	−178.9 (4)
C14—N3—C15—O1	−179.3 (3)	C8—C9—C10—C11	0.6 (7)
C8—N3—C15—C16	174.8 (3)	C9—C10—C11—C12	0.5 (7)
C15—N3—C8—C9	98.8 (4)	C10—C11—C12—C13	−1.2 (6)
C8—N3—C14—N1	6.1 (5)	C11—C12—C13—C8	0.9 (6)
C8—N3—C15—O1	−3.1 (5)	O1—C15—C16—N4	1.1 (6)
C8—N3—C14—N2	−175.7 (3)	O1—C15—C16—C17	179.1 (4)
C15—N3—C14—N2	0.3 (5)	N3—C15—C16—C17	1.3 (5)
C15—N3—C8—C13	−79.2 (4)	N3—C15—C16—N4	−176.6 (3)
C14—N3—C15—C16	−1.3 (5)	C15—C16—C17—S1	−178.7 (3)
C14—N3—C8—C9	−85.0 (4)	C15—C16—C17—N2	−0.3 (6)
C15—N3—C14—N1	−177.8 (3)	N4—C16—C17—N2	177.7 (4)
C18—N4—C16—C15	178.7 (4)	N4—C16—C17—S1	−0.7 (4)
C16—N4—C18—S1	−0.4 (5)	S2—C19—C20—C21	−178 (12)
C18—N4—C16—C17	0.7 (5)

Symmetry codes: (i) −x+1, −y+1, −z+3; (ii) −x+1, −y+1, −z+2; (iii) −y+3/2, x, −z+3/2; (iv) −y+3/2, x, −z+1/2; (v) y, −x+3/2, −z+3/2; (vi) y, −x+3/2, −z+1/2; (vii) −y+1, x+1/2, z−1/2; (viii) y, −x+3/2, −z+5/2; (ix) −y+3/2, x, −z+5/2; (x) y−1/2, −x+1, z+1/2; (xi) x, y, z+1; (xii) x, y, z−1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N4^v	0.86	2.38	3.069 (4)	138
C19—H19A···S1	0.97	2.67	3.275 (9)	120

Symmetry code: (v) y, −x+3/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₀N₄OS₂
M_r	408.53
Crystal system, space group	Tetragonal, P4₂/n
Temperature (K)	292
a, c (Å)	23.3140 (6), 7.7925 (4)
V (Å³)	4235.6 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.30 × 0.20 × 0.06

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	29639, 3737, 2138
R_int	0.080
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.183, 1.04
No. of reflections	3737
No. of parameters	268
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.30

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001), SHELXTL.

Selected geometric parameters (Å, º) top

S1—C17	1.739 (4)	N1—C14	1.345 (4)
S1—C18	1.758 (5)	N2—C17	1.353 (5)
S2—C18	1.798 (8)	N2—C14	1.309 (5)
S2—C19	1.776 (12)	N3—C15	1.413 (5)
S2'—C19'	1.714 (17)	N3—C8	1.447 (4)
S2'—C18	1.740 (11)	N3—C14	1.394 (5)
O1—C15	1.223 (5)	N4—C16	1.387 (5)
N1—C7	1.442 (5)	N4—C18	1.281 (6)

C17—S1—C18	88.2 (2)	O1—C15—N3	119.9 (3)
C18—S2—C19	102.8 (5)	O1—C15—C16	127.6 (3)
C18—S2'—C19'	115.0 (8)	N3—C15—C16	112.5 (3)
C7—N1—C14	121.1 (3)	N4—C16—C15	123.7 (3)
C14—N2—C17	113.6 (3)	N4—C16—C17	116.7 (3)
C8—N3—C14	120.3 (3)	S1—C17—C16	109.4 (3)
C8—N3—C15	116.9 (3)	N2—C17—C16	127.7 (4)
C14—N3—C15	122.8 (3)	S1—C17—N2	122.9 (3)
C16—N4—C18	109.9 (3)	S1—C18—S2'	117.0 (5)
N1—C7—C6	114.2 (3)	S1—C18—N4	115.9 (3)
N3—C8—C9	121.3 (3)	S2'—C18—N4	125.9 (5)
N3—C8—C13	118.6 (3)	S1—C18—S2	127.3 (4)
N2—C14—N3	123.8 (3)	S2—C18—N4	116.0 (4)
N1—C14—N3	116.9 (3)	S2—C19—C20	121.2 (8)
N1—C14—N2	119.3 (3)	S2'—C19'—C20'	112.7 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N4ⁱ	0.86	2.38	3.069 (4)	138

Symmetry code: (i) y, −x+3/2, −z+3/2.

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