1-Allyl-3-methyl-3′,5′-diphenyl­spiro­[quinoxaline-2(1H),2′(3′H)-[1,3,4]thia­diazole]

Anothane, C.A.; Bouhfid, R.; Zouihri, H.; Essassi, E.M.; Ng, S.W.

doi:10.1107/S1600536810046994

organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3227

https://doi.org/10.1107/S1600536810046994

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1-Allyl-3-methyl-3′,5′-diphenylspiro[quinoxaline-2(1H),2′(3′H)-[1,3,4]thiadiazole]

Caleb Ahoya Anothane,^a Rachid Bouhfid,^a Hafid Zouihri,^a El Mokhtar Essassi ^a and Seik Weng Ng ^b ^*

^aLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 9 November 2010; accepted 12 November 2010; online 20 November 2010)

In the title spiro compound, C₂₅H₂₂N₄S, the planar quinoxaline (r.m.s. deviation = 0.070 Å) and planar thiadiazole (r.m.s. deviation = 0.060 Å) ring systems share a common C atom; their mean planes are aligned at 89.7 (1)°. The thiazole ring possesses two aromatic ring substituents and is nearly coplanar with these rings [the dihedral angles between the thiadiazole and phenyl rings are 5.7 (1) and 10.7 (1)°]. The allyl unit is disordered over two positions in a 0.65 (1):0.35 (1) ratio.

Related literature

For pharmacologically active compounds derived from the 1,3-dipolar addition of diphenylnitrilimine to double bonds, see: Ahabchane & Essassi (2000 ); Canara et al. (2004 ); Ghomsi et al. (2004 ); Mustaphil et al. (2005 ).

Experimental

Crystal data

C₂₅H₂₂N₄S
M_r = 410.53
Triclinic, $[P \overline 1]$
a = 7.9201 (1) Å
b = 10.0713 (1) Å
c = 13.6642 (2) Å
α = 78.296 (1)°
β = 81.277 (1)°
γ = 89.826 (1)°
V = 1054.50 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 293 K
0.40 × 0.10 × 0.10 mm

Data collection

Bruker X8 APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.818, T_max = 0.862
38334 measured reflections
8514 independent reflections
5771 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.164
S = 1.03
8514 reflections
291 parameters
28 restraints
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810046994/nk2073sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810046994/nk2073Isup2.hkl

checkCIF report

Comment top

In our studies on pharmacologically active compounds, we have used diphenylnitrilimine to undergo 1,3-dipolar additions to double bonds (Ahabchane & Essassi, 2000; Canara et al., 2004; Ghomsi et al., 2004; Mustaphil et al., 2005). In the present study, this compound reacts with an aromatic thione to yield the title spiro compound (Scheme I, Fig. 1). The quinoxaline and the thiadiazole ring systems share a common C atom; their mean planes are aligned at 89.7 (1)°.

Related literature top

For pharmacologically active compounds derived from the 1,3-dipolar addition of diphenylnitrilimine to double bonds, see: Ahabchane & Essassi (2000); Canara et al. (2004); Ghomsi et al. (2004); Mustaphil et al. (2005).

Experimental top

To a solution of 1-allyl-3-methylquinoxaline-2-thione (1.00 g, 4.62 mmol) and diphenylnitrilimine (1.28 g, 5.55 mmol) in THF (20 ml) was added triethylamine (0.78 ml. 5.55 mmol). The mixture was heated for 24 h. The precipitate was recovered by filtration and was separated by chromatography on silica gel (hexane/ethyl acetate: 9/1). The title compound was obtained as yellow crystals upon evaporation of the solvent.

Structure description top

For pharmacologically active compounds derived from the 1,3-dipolar addition of diphenylnitrilimine to double bonds, see: Ahabchane & Essassi (2000); Canara et al. (2004); Ghomsi et al. (2004); Mustaphil et al. (2005).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Displacement ellipsoid plot of C₂₅H₂₂N₄S at the 50% probability level; hydrogen atoms are drawn as arbitrary radius. The minor disorder component is not shown.

1-Allyl-3-methyl-3',5'-diphenylspiro[quinoxaline- 2(1H),2'(3'H)-[1,3,4]thiadiazole] top

Crystal data top

C₂₅H₂₂N₄S	Z = 2
M_r = 410.53	F(000) = 432
Triclinic, P1	D_x = 1.293 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9201 (1) Å	Cell parameters from 9958 reflections
b = 10.0713 (1) Å	θ = 2.3–33.0°
c = 13.6642 (2) Å	µ = 0.17 mm⁻¹
α = 78.296 (1)°	T = 293 K
β = 81.277 (1)°	Prism, yellow
γ = 89.826 (1)°	0.40 × 0.10 × 0.10 mm
V = 1054.50 (2) Å³

Data collection top

Bruker X8 APEXII diffractometer	8514 independent reflections
Radiation source: fine-focus sealed tube	5771 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
φ and ω scans	θ_max = 33.9°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.818, T_max = 0.862	k = −15→15
38334 measured reflections	l = −21→21

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.164	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0836P)² + 0.1531P] where P = (F_o² + 2F_c²)/3
8514 reflections	(Δ/σ)_max = 0.001
291 parameters	Δρ_max = 0.32 e Å⁻³
28 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₅H₂₂N₄S	γ = 89.826 (1)°
M_r = 410.53	V = 1054.50 (2) Å³
Triclinic, P1	Z = 2
a = 7.9201 (1) Å	Mo Kα radiation
b = 10.0713 (1) Å	µ = 0.17 mm⁻¹
c = 13.6642 (2) Å	T = 293 K
α = 78.296 (1)°	0.40 × 0.10 × 0.10 mm
β = 81.277 (1)°

Data collection top

Bruker X8 APEXII diffractometer	8514 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5771 reflections with I > 2σ(I)
T_min = 0.818, T_max = 0.862	R_int = 0.022
38334 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	28 restraints
wR(F²) = 0.164	H-atom parameters constrained
S = 1.03	Δρ_max = 0.32 e Å⁻³
8514 reflections	Δρ_min = −0.20 e Å⁻³
291 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.55728 (4)	0.85155 (3)	0.59838 (2)	0.04746 (11)
N1	0.50074 (13)	0.71267 (12)	0.79755 (8)	0.0449 (2)
N2	0.15933 (13)	0.76834 (10)	0.77459 (8)	0.0433 (2)
N3	0.50993 (16)	0.59101 (10)	0.66315 (9)	0.0507 (3)
N4	0.64611 (15)	0.60663 (10)	0.58661 (9)	0.0470 (2)
C1	0.8280 (5)	0.5283 (5)	0.9283 (4)	0.0709 (12)	0.654 (11)
H1A	0.9040	0.5982	0.9290	0.085*	0.654 (11)
H1B	0.8382	0.4425	0.9674	0.085*	0.654 (11)
C2	0.7059 (6)	0.5510 (3)	0.8718 (4)	0.0527 (9)	0.654 (11)
H2	0.6314	0.4796	0.8723	0.063*	0.654 (11)
C1'	0.8401 (10)	0.5022 (8)	0.8777 (11)	0.085 (3)	0.346 (11)
H1'1	0.9090	0.5189	0.8148	0.102*	0.346 (11)
H1'2	0.8650	0.4320	0.9287	0.102*	0.346 (11)
C2'	0.7060 (13)	0.5787 (8)	0.8948 (4)	0.0579 (19)	0.346 (11)
H2'	0.6338	0.5656	0.9565	0.070*	0.346 (11)
C3	0.68125 (17)	0.68768 (17)	0.80623 (11)	0.0584 (4)
H3A	0.7262	0.7583	0.8348	0.070*
H3B	0.7456	0.6924	0.7393	0.070*
C4	0.39793 (16)	0.76799 (11)	0.86969 (9)	0.0406 (2)
C5	0.4548 (2)	0.79361 (17)	0.95621 (12)	0.0577 (3)
H5	0.5670	0.7761	0.9662	0.069*
C6	0.3444 (3)	0.84499 (19)	1.02685 (13)	0.0684 (4)
H6	0.3840	0.8623	1.0839	0.082*
C7	0.1772 (3)	0.87124 (17)	1.01491 (12)	0.0649 (4)
H7	0.1043	0.9053	1.0634	0.078*
C8	0.11982 (19)	0.84633 (14)	0.93028 (11)	0.0527 (3)
H8	0.0071	0.8637	0.9216	0.063*
C9	0.22789 (15)	0.79542 (11)	0.85726 (9)	0.0400 (2)
C10	0.25755 (16)	0.72698 (12)	0.70458 (10)	0.0432 (2)
C11	0.1835 (2)	0.69551 (19)	0.61697 (13)	0.0644 (4)
H11A	0.0655	0.7193	0.6226	0.097*
H11B	0.1924	0.6004	0.6172	0.097*
H11C	0.2452	0.7467	0.5549	0.097*
C12	0.44934 (15)	0.71136 (11)	0.70212 (9)	0.0396 (2)
C13	0.44801 (17)	0.45774 (11)	0.70791 (10)	0.0446 (3)
C14	0.3295 (2)	0.43079 (15)	0.79643 (12)	0.0581 (4)
H14	0.2914	0.5007	0.8287	0.070*
C15	0.2686 (2)	0.29836 (16)	0.83610 (14)	0.0659 (4)
H15	0.1879	0.2807	0.8945	0.079*
C16	0.3252 (2)	0.19377 (15)	0.79093 (16)	0.0700 (5)
H16	0.2842	0.1056	0.8185	0.084*
C17	0.4432 (2)	0.22055 (14)	0.70430 (15)	0.0648 (4)
H17	0.4825	0.1496	0.6736	0.078*
C18	0.50517 (19)	0.35175 (13)	0.66164 (12)	0.0513 (3)
H18	0.5843	0.3684	0.6025	0.062*
C19	0.68575 (16)	0.73197 (11)	0.54723 (9)	0.0412 (2)
C20	0.82935 (16)	0.77223 (12)	0.46545 (9)	0.0411 (2)
C21	0.92074 (19)	0.67363 (16)	0.42316 (11)	0.0535 (3)
H21	0.8911	0.5823	0.4474	0.064*
C22	1.0549 (2)	0.7115 (2)	0.34546 (13)	0.0680 (4)
H22	1.1148	0.6456	0.3169	0.082*
C23	1.1010 (2)	0.8468 (2)	0.30971 (13)	0.0704 (5)
H23	1.1924	0.8716	0.2576	0.085*
C24	1.0122 (2)	0.94469 (19)	0.35095 (13)	0.0668 (4)
H24	1.0432	1.0358	0.3267	0.080*
C25	0.87667 (19)	0.90801 (14)	0.42849 (11)	0.0538 (3)
H25	0.8167	0.9747	0.4561	0.065*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0582 (2)	0.03341 (13)	0.04398 (17)	0.00401 (11)	0.00390 (13)	−0.00090 (10)
N1	0.0345 (5)	0.0579 (6)	0.0390 (5)	0.0047 (4)	−0.0036 (4)	−0.0039 (4)
N2	0.0388 (5)	0.0427 (5)	0.0474 (5)	0.0021 (4)	−0.0070 (4)	−0.0069 (4)
N3	0.0578 (6)	0.0322 (4)	0.0531 (6)	0.0008 (4)	0.0132 (5)	−0.0036 (4)
N4	0.0507 (6)	0.0375 (4)	0.0478 (6)	0.0013 (4)	0.0057 (5)	−0.0070 (4)
C1	0.0616 (17)	0.0673 (18)	0.077 (2)	−0.0016 (14)	−0.0272 (18)	0.0131 (17)
C2	0.0502 (14)	0.0530 (13)	0.0565 (19)	0.0043 (11)	−0.0175 (15)	−0.0084 (13)
C1'	0.071 (4)	0.072 (4)	0.103 (6)	0.016 (3)	−0.015 (4)	0.002 (4)
C2'	0.056 (3)	0.074 (4)	0.047 (3)	0.008 (3)	−0.008 (2)	−0.018 (2)
C3	0.0351 (6)	0.0824 (10)	0.0485 (7)	0.0064 (6)	−0.0035 (5)	0.0055 (7)
C4	0.0419 (6)	0.0393 (5)	0.0373 (5)	−0.0035 (4)	−0.0028 (4)	−0.0028 (4)
C5	0.0560 (8)	0.0696 (9)	0.0488 (7)	−0.0062 (7)	−0.0127 (6)	−0.0113 (6)
C6	0.0862 (12)	0.0760 (10)	0.0476 (8)	−0.0061 (9)	−0.0109 (8)	−0.0226 (7)
C7	0.0810 (11)	0.0617 (8)	0.0523 (8)	0.0085 (8)	0.0023 (7)	−0.0215 (7)
C8	0.0535 (7)	0.0476 (6)	0.0539 (7)	0.0087 (5)	0.0015 (6)	−0.0106 (5)
C9	0.0413 (6)	0.0346 (5)	0.0412 (6)	−0.0003 (4)	−0.0016 (4)	−0.0043 (4)
C10	0.0432 (6)	0.0420 (5)	0.0447 (6)	0.0019 (4)	−0.0094 (5)	−0.0079 (4)
C11	0.0673 (10)	0.0751 (10)	0.0600 (9)	0.0064 (8)	−0.0238 (8)	−0.0249 (8)
C12	0.0429 (6)	0.0347 (4)	0.0386 (5)	0.0029 (4)	−0.0020 (4)	−0.0046 (4)
C13	0.0450 (6)	0.0344 (5)	0.0506 (7)	−0.0022 (4)	−0.0066 (5)	−0.0004 (4)
C14	0.0583 (8)	0.0463 (6)	0.0601 (8)	−0.0068 (6)	0.0047 (7)	0.0009 (6)
C15	0.0617 (9)	0.0574 (8)	0.0671 (9)	−0.0179 (7)	−0.0073 (8)	0.0125 (7)
C16	0.0749 (11)	0.0423 (6)	0.0889 (12)	−0.0179 (7)	−0.0306 (10)	0.0090 (7)
C17	0.0720 (10)	0.0383 (6)	0.0876 (12)	−0.0024 (6)	−0.0275 (9)	−0.0097 (7)
C18	0.0541 (7)	0.0392 (5)	0.0615 (8)	−0.0002 (5)	−0.0122 (6)	−0.0099 (5)
C19	0.0466 (6)	0.0377 (5)	0.0369 (5)	0.0017 (4)	−0.0022 (4)	−0.0051 (4)
C20	0.0414 (6)	0.0463 (6)	0.0342 (5)	−0.0002 (4)	−0.0053 (4)	−0.0053 (4)
C21	0.0511 (7)	0.0577 (7)	0.0533 (7)	0.0037 (6)	−0.0035 (6)	−0.0185 (6)
C22	0.0553 (9)	0.0885 (12)	0.0608 (9)	0.0084 (8)	0.0044 (7)	−0.0265 (9)
C23	0.0495 (8)	0.1031 (14)	0.0499 (8)	−0.0017 (8)	0.0073 (6)	−0.0061 (8)
C24	0.0571 (9)	0.0690 (9)	0.0609 (9)	−0.0085 (7)	0.0044 (7)	0.0082 (7)
C25	0.0539 (8)	0.0477 (6)	0.0519 (7)	−0.0015 (5)	0.0028 (6)	0.0000 (5)

Geometric parameters (Å, º) top

S1—C19	1.7585 (12)	C8—C9	1.3917 (17)
S1—C12	1.8872 (12)	C8—H8	0.9300
N1—C4	1.3863 (15)	C10—C11	1.4986 (19)
N1—C12	1.4263 (16)	C10—C12	1.5227 (17)
N1—C3	1.4692 (16)	C11—H11A	0.9600
N2—C10	1.2757 (16)	C11—H11B	0.9600
N2—C9	1.3991 (17)	C11—H11C	0.9600
N3—N4	1.3689 (15)	C13—C18	1.3887 (18)
N3—C13	1.4128 (15)	C13—C14	1.394 (2)
N3—C12	1.4709 (14)	C14—C15	1.391 (2)
N4—C19	1.2874 (15)	C14—H14	0.9300
C1—C2	1.318 (3)	C15—C16	1.367 (3)
C1—H1A	0.9300	C15—H15	0.9300
C1—H1B	0.9300	C16—C17	1.373 (3)
C2—C3	1.512 (3)	C16—H16	0.9300
C2—H2	0.9300	C17—C18	1.390 (2)
C1'—C2'	1.330 (5)	C17—H17	0.9300
C1'—H1'1	0.9300	C18—H18	0.9300
C1'—H1'2	0.9300	C19—C20	1.4629 (17)
C2'—C3	1.496 (4)	C20—C25	1.3896 (18)
C2'—H2'	0.9300	C20—C21	1.3948 (18)
C3—H3A	0.9700	C21—C22	1.378 (2)
C3—H3B	0.9700	C21—H21	0.9300
C4—C5	1.3975 (19)	C22—C23	1.381 (3)
C4—C9	1.4025 (17)	C22—H22	0.9300
C5—C6	1.381 (2)	C23—C24	1.374 (3)
C5—H5	0.9300	C23—H23	0.9300
C6—C7	1.377 (3)	C24—C25	1.382 (2)
C6—H6	0.9300	C24—H24	0.9300
C7—C8	1.373 (2)	C25—H25	0.9300
C7—H7	0.9300

C19—S1—C12	89.97 (5)	C10—C11—H11A	109.5
C4—N1—C12	120.78 (10)	C10—C11—H11B	109.5
C4—N1—C3	120.12 (11)	H11A—C11—H11B	109.5
C12—N1—C3	117.17 (10)	C10—C11—H11C	109.5
C10—N2—C9	119.02 (11)	H11A—C11—H11C	109.5
N4—N3—C13	117.81 (10)	H11B—C11—H11C	109.5
N4—N3—C12	118.38 (9)	N1—C12—N3	111.72 (10)
C13—N3—C12	123.41 (10)	N1—C12—C10	112.44 (10)
C19—N4—N3	112.75 (10)	N3—C12—C10	111.80 (10)
C2—C1—H1A	120.0	N1—C12—S1	112.47 (8)
C2—C1—H1B	120.0	N3—C12—S1	100.87 (7)
H1A—C1—H1B	120.0	C10—C12—S1	106.89 (8)
C1—C2—C3	123.1 (3)	C18—C13—C14	119.45 (12)
C1—C2—H2	118.5	C18—C13—N3	119.04 (12)
C3—C2—H2	118.5	C14—C13—N3	121.50 (12)
C2'—C1'—H1'1	120.0	C15—C14—C13	119.39 (15)
C2'—C1'—H1'2	120.0	C15—C14—H14	120.3
H1'1—C1'—H1'2	120.0	C13—C14—H14	120.3
C1'—C2'—C3	114.3 (7)	C16—C15—C14	121.27 (17)
C1'—C2'—H2'	122.9	C16—C15—H15	119.4
C3—C2'—H2'	122.9	C14—C15—H15	119.4
N1—C3—C2'	113.4 (4)	C15—C16—C17	119.15 (14)
N1—C3—C2	112.4 (2)	C15—C16—H16	120.4
N1—C3—H3A	109.1	C17—C16—H16	120.4
C2'—C3—H3A	92.9	C16—C17—C18	121.24 (16)
C2—C3—H3A	109.1	C16—C17—H17	119.4
N1—C3—H3B	109.1	C18—C17—H17	119.4
C2'—C3—H3B	122.5	C13—C18—C17	119.49 (15)
C2—C3—H3B	109.1	C13—C18—H18	120.3
H3A—C3—H3B	107.9	C17—C18—H18	120.3
N1—C4—C5	122.78 (12)	N4—C19—C20	122.02 (11)
N1—C4—C9	118.77 (11)	N4—C19—S1	115.81 (9)
C5—C4—C9	118.41 (12)	C20—C19—S1	122.17 (9)
C6—C5—C4	119.98 (15)	C25—C20—C21	119.00 (12)
C6—C5—H5	120.0	C25—C20—C19	121.04 (11)
C4—C5—H5	120.0	C21—C20—C19	119.96 (11)
C7—C6—C5	121.61 (15)	C22—C21—C20	120.01 (15)
C7—C6—H6	119.2	C22—C21—H21	120.0
C5—C6—H6	119.2	C20—C21—H21	120.0
C8—C7—C6	118.93 (14)	C21—C22—C23	120.40 (16)
C8—C7—H7	120.5	C21—C22—H22	119.8
C6—C7—H7	120.5	C23—C22—H22	119.8
C7—C8—C9	120.97 (14)	C24—C23—C22	120.08 (15)
C7—C8—H8	119.5	C24—C23—H23	120.0
C9—C8—H8	119.5	C22—C23—H23	120.0
C8—C9—N2	117.88 (12)	C23—C24—C25	120.06 (16)
C8—C9—C4	120.09 (12)	C23—C24—H24	120.0
N2—C9—C4	121.98 (11)	C25—C24—H24	120.0
N2—C10—C11	119.02 (12)	C24—C25—C20	120.45 (14)
N2—C10—C12	123.99 (11)	C24—C25—H25	119.8
C11—C10—C12	116.96 (12)	C20—C25—H25	119.8

C13—N3—N4—C19	176.13 (12)	C13—N3—C12—S1	−171.95 (12)
C12—N3—N4—C19	−10.90 (18)	N2—C10—C12—N1	15.62 (17)
C4—N1—C3—C2'	67.3 (4)	C11—C10—C12—N1	−166.40 (12)
C12—N1—C3—C2'	−128.4 (4)	N2—C10—C12—N3	142.24 (12)
C4—N1—C3—C2	86.4 (3)	C11—C10—C12—N3	−39.79 (15)
C12—N1—C3—C2	−109.3 (3)	N2—C10—C12—S1	−108.26 (12)
C1'—C2'—C3—N1	144.0 (11)	C11—C10—C12—S1	69.71 (13)
C1'—C2'—C3—C2	53.6 (12)	C19—S1—C12—N1	106.99 (9)
C1—C2—C3—N1	−147.7 (7)	C19—S1—C12—N3	−12.17 (9)
C12—N1—C4—C5	−168.30 (12)	C19—S1—C12—C10	−129.14 (9)
C3—N1—C4—C5	−4.53 (19)	N4—N3—C13—C18	−11.6 (2)
C12—N1—C4—C9	13.84 (17)	C12—N3—C13—C18	175.83 (12)
C3—N1—C4—C9	177.61 (11)	N4—N3—C13—C14	169.30 (14)
N1—C4—C5—C6	−177.99 (14)	C12—N3—C13—C14	−3.3 (2)
C9—C4—C5—C6	−0.1 (2)	C18—C13—C14—C15	−0.9 (2)
C4—C5—C6—C7	0.5 (3)	N3—C13—C14—C15	178.20 (15)
C5—C6—C7—C8	−0.4 (3)	C13—C14—C15—C16	1.2 (3)
C6—C7—C8—C9	0.0 (2)	C14—C15—C16—C17	−0.5 (3)
C7—C8—C9—N2	177.98 (13)	C15—C16—C17—C18	−0.4 (3)
C7—C8—C9—C4	0.4 (2)	C14—C13—C18—C17	0.0 (2)
C10—N2—C9—C8	177.11 (12)	N3—C13—C18—C17	−179.11 (14)
C10—N2—C9—C4	−5.33 (17)	C16—C17—C18—C13	0.6 (2)
N1—C4—C9—C8	177.66 (11)	N3—N4—C19—C20	178.86 (11)
C5—C4—C9—C8	−0.29 (18)	N3—N4—C19—S1	−0.79 (16)
N1—C4—C9—N2	0.16 (17)	C12—S1—C19—N4	8.47 (11)
C5—C4—C9—N2	−177.80 (12)	C12—S1—C19—C20	−171.19 (11)
C9—N2—C10—C11	178.88 (12)	N4—C19—C20—C25	−175.82 (13)
C9—N2—C10—C12	−3.19 (18)	S1—C19—C20—C25	3.81 (18)
C4—N1—C12—N3	−147.06 (11)	N4—C19—C20—C21	4.4 (2)
C3—N1—C12—N3	48.70 (15)	S1—C19—C20—C21	−175.98 (10)
C4—N1—C12—C10	−20.40 (15)	C25—C20—C21—C22	−0.5 (2)
C3—N1—C12—C10	175.36 (11)	C19—C20—C21—C22	179.35 (14)
C4—N1—C12—S1	100.32 (11)	C20—C21—C22—C23	0.7 (3)
C3—N1—C12—S1	−63.91 (13)	C21—C22—C23—C24	−0.6 (3)
N4—N3—C12—N1	−104.20 (13)	C22—C23—C24—C25	0.2 (3)
C13—N3—C12—N1	68.34 (16)	C23—C24—C25—C20	0.1 (3)
N4—N3—C12—C10	128.80 (13)	C21—C20—C25—C24	0.0 (2)
C13—N3—C12—C10	−58.66 (16)	C19—C20—C25—C24	−179.75 (14)
N4—N3—C12—S1	15.50 (14)

Experimental details

Crystal data
Chemical formula	C₂₅H₂₂N₄S
M_r	410.53
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.9201 (1), 10.0713 (1), 13.6642 (2)
α, β, γ (°)	78.296 (1), 81.277 (1), 89.826 (1)
V (Å³)	1054.50 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.17
Crystal size (mm)	0.40 × 0.10 × 0.10

Data collection
Diffractometer	Bruker X8 APEXII
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.818, 0.862
No. of measured, independent and observed [I > 2σ(I)] reflections	38334, 8514, 5771
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.785

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.164, 1.03
No. of reflections	8514
No. of parameters	291
No. of restraints	28
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.20

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Acknowledgements

We thank Université Mohammed V-Agdal and the University of Malaya for supporting this study.

References

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