1-Allyl-4-(1,3-benzothia­zol-2-yl)-5-methyl-2-phenyl-1H-pyrazol-3(2H)-one

Chakib, I.; Zerzouf, A.; Zouihri, H.; Essassi, E.M.; Ng, S.W.

doi:10.1107/S1600536810040316

organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o2842

https://doi.org/10.1107/S1600536810040316

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1-Allyl-4-(1,3-benzothiazol-2-yl)-5-methyl-2-phenyl-1H-pyrazol-3(2H)-one

Imane Chakib,^a Abdelfettah Zerzouf,^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 6 October 2010; accepted 8 October 2010; online 20 October 2010)

The title compound, C₂₀H₁₇N₃OS, is a 1H-pyrazol-3(2H)-one having aromatic 4-(1,3-benzothiazol-2-yl)- and 2-phenyl substituents. The five-membered ring and fused ring system are planar, the r.m.s. deviations being 0.021 and 0.005 Å, respectively. The five-membered ring is aligned at 7.9 (2)° with respect to the fused-ring system. The allyl and phenyl parts of the molecule are both disordered over two positions in a 1:1 ratio. Weak intermolecular C—H⋯O hydrogen bonding is present in the crystal structure.

Related literature

For the structure of a related compound (E)-4-(2,3-dihydro-1,3-benzothiazol-2-ylidene)-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one, see: Chakibe et al. (2010 ).

Experimental

Crystal data

C₂₀H₁₇N₃OS
M_r = 347.43
Orthorhombic, P b c a
a = 17.8734 (5) Å
b = 10.4297 (2) Å
c = 18.9578 (4) Å
V = 3534.00 (14) Å³
Z = 8
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 293 K
0.30 × 0.30 × 0.25 mm

Data collection

Bruker X8 APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.944, T_max = 0.953
18349 measured reflections
3678 independent reflections
2341 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.172
S = 1.00
3678 reflections
227 parameters
17 restraints
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1ⁱ	0.93	2.59	3.318 (3)	135
C12—H12A⋯O1ⁱⁱ	0.97	2.51	3.404 (4)	152
C12—H12C⋯O1ⁱⁱ	0.97	2.48	3.404 (4)	159
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); 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/S1600536810040316/xu5047sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810040316/xu5047Isup2.hkl

checkCIF report

Comment top

(E)-4-(2,3-Dihydro-1,3-benzothiazol-2-ylidene)-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one is an amine that can under a nucleophilic substitution with organo bromides to form 2-substituted derivatives if tetra-n-butyl ammonium bromide is used as catalyst. In this study, the compound is reacted with allyl bromide to yield the title compound (Scheme I, Fig. 1).

Related literature top

For the structure of a related compound (E)-4-(2,3-dihydro-1,3-benzothiazol-2-ylidene)-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one, see: Chakibe et al. (2010).

Experimental top

To a solution of (E)-4-(2,3-dihydro-1,3-benzothiazol-2-ylidene)-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one (1 g, 3.25 mmol) in DMF (50 ml), was added sodium carbonate (2.5 g, 23 mmol), tetra-n-butyl ammonium bromide (0.15 g, 1 mmol) and allyl bromide (5.6 g, 46 mmol). The mixture was stirred for 24 h at room temperature. The solid material was removed by filtration and the solution was evaporated under reduced. The residue was washed with dichloromethane and hexane, and the recrystallized from ethanol to afford the title compound as colorless crystals.

Structure description top

For the structure of a related compound (E)-4-(2,3-dihydro-1,3-benzothiazol-2-ylidene)-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one, see: Chakibe et al. (2010).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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. Thermal ellipsoid plot (Barbour, 2001) of C₂₀H₁₇N₃OS at the 50% probability level; hydrogen atoms are drawn as arbitrary radius. The disorder is not shown

1-Allyl-4-(1,3-benzothiazol-2-yl)-5-methyl-2-phenyl- 1H-pyrazol-3(2H)-one top

Crystal data top

C₂₀H₁₇N₃OS	F(000) = 1456
M_r = 347.43	D_x = 1.306 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3745 reflections
a = 17.8734 (5) Å	θ = 2.3–22.5°
b = 10.4297 (2) Å	µ = 0.20 mm⁻¹
c = 18.9578 (4) Å	T = 293 K
V = 3534.00 (14) Å³	Prism, colorless
Z = 8	0.30 × 0.30 × 0.25 mm

Data collection top

Bruker X8 APEXII diffractometer	3678 independent reflections
Radiation source: fine-focus sealed tube	2341 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
φ and ω scans	θ_max = 26.6°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −22→21
T_min = 0.944, T_max = 0.953	k = −13→12
18349 measured reflections	l = −23→23

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) = 0.172	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.096P)² + 0.8646P] where P = (F_o² + 2F_c²)/3
3678 reflections	(Δ/σ)_max = 0.001
227 parameters	Δρ_max = 0.32 e Å⁻³
17 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₂₀H₁₇N₃OS	V = 3534.00 (14) Å³
M_r = 347.43	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 17.8734 (5) Å	µ = 0.20 mm⁻¹
b = 10.4297 (2) Å	T = 293 K
c = 18.9578 (4) Å	0.30 × 0.30 × 0.25 mm

Data collection top

Bruker X8 APEXII diffractometer	3678 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2341 reflections with I > 2σ(I)
T_min = 0.944, T_max = 0.953	R_int = 0.032
18349 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	17 restraints
wR(F²) = 0.172	H-atom parameters constrained
S = 1.00	Δρ_max = 0.32 e Å⁻³
3678 reflections	Δρ_min = −0.25 e Å⁻³
227 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.54022 (4)	0.59623 (7)	0.57529 (3)	0.0590 (2)
O1	0.63189 (12)	0.5096 (2)	0.45761 (10)	0.0808 (6)
N1	0.61613 (12)	0.7853 (2)	0.62953 (11)	0.0590 (6)
N2	0.79529 (13)	0.6762 (2)	0.48741 (11)	0.0593 (6)
N3	0.75432 (13)	0.5809 (2)	0.45335 (11)	0.0627 (6)
C1	0.50073 (15)	0.6812 (2)	0.64448 (12)	0.0531 (6)
C2	0.43115 (17)	0.6640 (3)	0.67650 (14)	0.0669 (7)
H2	0.3989	0.5995	0.6617	0.080*
C3	0.41164 (19)	0.7448 (3)	0.73035 (15)	0.0762 (9)
H3	0.3654	0.7349	0.7522	0.091*
C4	0.4595 (2)	0.8412 (3)	0.75287 (16)	0.0798 (9)
H4	0.4454	0.8943	0.7900	0.096*
C5	0.52717 (19)	0.8589 (3)	0.72110 (15)	0.0743 (8)
H5	0.5587	0.9242	0.7362	0.089*
C6	0.54904 (16)	0.7785 (2)	0.66569 (12)	0.0566 (6)
C7	0.61898 (14)	0.6956 (2)	0.58142 (11)	0.0495 (6)
C8	0.68208 (17)	0.5800 (3)	0.48056 (13)	0.0603 (7)
C9	0.68293 (15)	0.6721 (2)	0.53608 (12)	0.0518 (6)
C10	0.75276 (15)	0.7255 (2)	0.53898 (12)	0.0548 (6)
C11	0.78327 (19)	0.8222 (3)	0.58934 (16)	0.0760 (8)
H11A	0.8269	0.8617	0.5693	0.114*
H11B	0.7965	0.7806	0.6327	0.114*
H11C	0.7461	0.8865	0.5984	0.114*
C12	0.87637 (17)	0.6862 (3)	0.48056 (16)	0.0746 (8)
H12A	0.8914	0.7755	0.4806	0.090*	0.50
H12B	0.8926	0.6475	0.4366	0.090*	0.50
H12C	0.8825	0.7782	0.4852	0.090*	0.50
H12D	0.8812	0.6708	0.4303	0.090*	0.50
C13	0.9121 (11)	0.6151 (15)	0.5440 (7)	0.101 (3)	0.50
H13	0.8915	0.5398	0.5616	0.121*	0.50
C14	0.9722 (11)	0.6652 (18)	0.5718 (9)	0.139 (4)	0.50
H14A	0.9920	0.7407	0.5535	0.166*	0.50
H14B	0.9953	0.6254	0.6099	0.166*	0.50
C13'	0.9175 (11)	0.5938 (15)	0.5294 (7)	0.101 (3)	0.50
H13'	0.9148	0.5076	0.5171	0.121*	0.50
C14'	0.9555 (11)	0.6196 (18)	0.5854 (8)	0.139 (4)	0.50
H14C	0.9603	0.7041	0.6004	0.166*	0.50
H14D	0.9781	0.5538	0.6107	0.166*	0.50
C15	0.7691 (10)	0.5140 (10)	0.3885 (4)	0.0510 (18)	0.50
C16	0.8277 (10)	0.4304 (14)	0.3741 (5)	0.0863 (18)	0.50
H16	0.8561	0.3969	0.4108	0.104*	0.50
C17	0.8437 (10)	0.3967 (13)	0.3048 (5)	0.105 (3)	0.50
H17	0.8829	0.3407	0.2951	0.126*	0.50
C18	0.8012 (11)	0.4466 (10)	0.2499 (4)	0.110 (4)	0.50
H18	0.8119	0.4241	0.2035	0.132*	0.50
C19	0.7426 (10)	0.5303 (12)	0.2643 (6)	0.102 (3)	0.50
H19	0.7142	0.5637	0.2275	0.123*	0.50
C20	0.7265 (9)	0.5640 (12)	0.3336 (7)	0.0714 (19)	0.50
H20	0.6874	0.6199	0.3432	0.086*	0.50
C15'	0.7791 (10)	0.5424 (10)	0.3848 (5)	0.0510 (18)	0.50
C16'	0.8326 (10)	0.4458 (14)	0.3884 (4)	0.0863 (18)	0.50
H16'	0.8571	0.4294	0.4308	0.104*	0.50
C17'	0.8494 (11)	0.3738 (12)	0.3288 (5)	0.105 (3)	0.50
H17'	0.8852	0.3092	0.3312	0.126*	0.50
C18'	0.8127 (11)	0.3984 (9)	0.2656 (4)	0.110 (4)	0.50
H18'	0.8240	0.3502	0.2257	0.132*	0.50
C19'	0.7593 (10)	0.4949 (13)	0.2620 (5)	0.102 (3)	0.50
H19'	0.7347	0.5113	0.2197	0.123*	0.50
C20'	0.7425 (9)	0.5669 (11)	0.3216 (7)	0.0714 (19)	0.50
H20'	0.7067	0.6315	0.3192	0.086*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0542 (4)	0.0698 (4)	0.0528 (4)	−0.0033 (3)	0.0062 (3)	−0.0106 (3)
O1	0.0647 (13)	0.1020 (15)	0.0756 (13)	−0.0228 (12)	0.0166 (10)	−0.0337 (12)
N1	0.0559 (14)	0.0630 (12)	0.0580 (12)	0.0042 (10)	0.0020 (10)	−0.0066 (10)
N2	0.0529 (14)	0.0655 (12)	0.0594 (12)	−0.0072 (11)	0.0080 (10)	−0.0040 (10)
N3	0.0568 (14)	0.0740 (13)	0.0573 (12)	−0.0097 (11)	0.0118 (11)	−0.0143 (10)
C1	0.0521 (16)	0.0634 (14)	0.0438 (12)	0.0102 (12)	−0.0007 (11)	0.0048 (10)
C2	0.0615 (18)	0.0812 (18)	0.0581 (15)	0.0026 (15)	0.0106 (13)	0.0007 (13)
C3	0.067 (2)	0.100 (2)	0.0611 (16)	0.0151 (18)	0.0163 (15)	0.0006 (15)
C4	0.084 (2)	0.090 (2)	0.0657 (17)	0.0216 (19)	0.0131 (17)	−0.0169 (16)
C5	0.075 (2)	0.0803 (18)	0.0677 (17)	0.0077 (16)	0.0047 (16)	−0.0213 (15)
C6	0.0589 (17)	0.0610 (14)	0.0500 (13)	0.0111 (13)	−0.0020 (12)	−0.0043 (11)
C7	0.0514 (15)	0.0534 (12)	0.0438 (11)	0.0041 (11)	−0.0018 (10)	0.0018 (10)
C8	0.0599 (17)	0.0689 (15)	0.0521 (13)	−0.0055 (14)	0.0088 (13)	−0.0060 (12)
C9	0.0538 (16)	0.0566 (13)	0.0450 (12)	0.0004 (12)	0.0022 (11)	−0.0006 (10)
C10	0.0558 (16)	0.0580 (13)	0.0507 (13)	−0.0014 (12)	0.0024 (12)	−0.0003 (11)
C11	0.070 (2)	0.0852 (19)	0.0725 (17)	−0.0151 (16)	0.0033 (15)	−0.0177 (15)
C12	0.0580 (19)	0.090 (2)	0.0763 (19)	−0.0105 (16)	0.0148 (15)	−0.0134 (16)
C13	0.072 (3)	0.124 (5)	0.108 (6)	0.039 (3)	−0.021 (4)	−0.065 (4)
C14	0.136 (8)	0.165 (9)	0.115 (6)	0.033 (7)	0.001 (5)	0.023 (6)
C13'	0.072 (3)	0.124 (5)	0.108 (6)	0.039 (3)	−0.021 (4)	−0.065 (4)
C14'	0.136 (8)	0.165 (9)	0.115 (6)	0.033 (7)	0.001 (5)	0.023 (6)
C15	0.059 (4)	0.031 (4)	0.0631 (17)	−0.024 (4)	0.0240 (16)	−0.001 (2)
C16	0.087 (3)	0.067 (3)	0.105 (4)	0.001 (3)	0.026 (4)	−0.022 (3)
C17	0.122 (5)	0.085 (5)	0.108 (8)	0.000 (4)	0.058 (7)	−0.028 (5)
C18	0.133 (8)	0.098 (8)	0.098 (5)	−0.045 (8)	0.057 (6)	−0.038 (5)
C19	0.100 (7)	0.149 (8)	0.0579 (19)	−0.034 (6)	0.029 (3)	−0.017 (3)
C20	0.069 (6)	0.102 (2)	0.043 (4)	−0.020 (3)	0.028 (3)	0.007 (2)
C15'	0.059 (4)	0.031 (4)	0.0631 (17)	−0.024 (4)	0.0240 (16)	−0.001 (2)
C16'	0.087 (3)	0.067 (3)	0.105 (4)	0.001 (3)	0.026 (4)	−0.022 (3)
C17'	0.122 (5)	0.085 (5)	0.108 (8)	0.000 (4)	0.058 (7)	−0.028 (5)
C18'	0.133 (8)	0.098 (8)	0.098 (5)	−0.045 (8)	0.057 (6)	−0.038 (5)
C19'	0.100 (7)	0.149 (8)	0.0579 (19)	−0.034 (6)	0.029 (3)	−0.017 (3)
C20'	0.069 (6)	0.102 (2)	0.043 (4)	−0.020 (3)	0.028 (3)	0.007 (2)

Geometric parameters (Å, º) top

S1—C1	1.733 (2)	C12—H12C	0.9701
S1—C7	1.752 (3)	C12—H12D	0.9701
O1—C8	1.238 (3)	C13—C14	1.305 (10)
N1—C7	1.307 (3)	C13—H13	0.9300
N1—C6	1.383 (3)	C14—H14A	0.9300
N2—C10	1.341 (3)	C14—H14B	0.9300
N2—N3	1.393 (3)	C13'—C14'	1.289 (9)
N2—C12	1.459 (3)	C13'—H13'	0.9300
N3—C8	1.391 (4)	C14'—H14C	0.9300
N3—C15'	1.430 (6)	C14'—H14D	0.9300
N3—C15	1.438 (6)	C15—C16	1.3900
C1—C6	1.392 (4)	C15—C20	1.3900
C1—C2	1.395 (4)	C16—C17	1.3900
C2—C3	1.369 (4)	C16—H16	0.9300
C2—H2	0.9300	C17—C18	1.3900
C3—C4	1.388 (5)	C17—H17	0.9300
C3—H3	0.9300	C18—C19	1.3900
C4—C5	1.363 (4)	C18—H18	0.9300
C4—H4	0.9300	C19—C20	1.3900
C5—C6	1.399 (4)	C19—H19	0.9300
C5—H5	0.9300	C20—H20	0.9300
C7—C9	1.451 (3)	C15'—C16'	1.3900
C8—C9	1.425 (3)	C15'—C20'	1.3900
C9—C10	1.368 (4)	C16'—C17'	1.3900
C10—C11	1.492 (4)	C16'—H16'	0.9300
C11—H11A	0.9600	C17'—C18'	1.3900
C11—H11B	0.9600	C17'—H17'	0.9300
C11—H11C	0.9600	C18'—C19'	1.3900
C12—C13'	1.525 (9)	C18'—H18'	0.9300
C12—C13	1.551 (8)	C19'—C20'	1.3900
C12—H12A	0.9700	C19'—H19'	0.9300
C12—H12B	0.9700	C20'—H20'	0.9300

C1—S1—C7	88.53 (12)	H12A—C12—H12B	108.5
C7—N1—C6	110.1 (2)	C13'—C12—H12C	121.0
C10—N2—N3	108.3 (2)	C13—C12—H12C	110.8
C10—N2—C12	126.9 (2)	C13'—C12—H12D	116.7
N3—N2—C12	122.1 (2)	H12C—C12—H12D	104.1
C8—N3—N2	108.7 (2)	C14—C13—C12	117.5 (15)
C8—N3—C15'	128.5 (7)	C14—C13—H13	121.3
N2—N3—C15'	117.3 (6)	C12—C13—H13	121.3
C8—N3—C15	118.9 (7)	C13—C14—H14A	120.0
N2—N3—C15	130.3 (6)	C13—C14—H14B	120.0
C6—C1—C2	121.4 (2)	H14A—C14—H14B	120.0
C6—C1—S1	109.81 (19)	C14'—C13'—C12	128.4 (15)
C2—C1—S1	128.8 (2)	C14'—C13'—H13'	115.8
C3—C2—C1	118.2 (3)	C12—C13'—H13'	115.8
C3—C2—H2	120.9	C13'—C14'—H14C	120.0
C1—C2—H2	120.9	C13'—C14'—H14D	120.0
C2—C3—C4	121.2 (3)	H14C—C14'—H14D	120.0
C2—C3—H3	119.4	C16—C15—C20	120.0
C4—C3—H3	119.4	C16—C15—N3	127.6 (11)
C5—C4—C3	120.6 (3)	C20—C15—N3	111.0 (10)
C5—C4—H4	119.7	C15—C16—C17	120.0
C3—C4—H4	119.7	C15—C16—H16	120.0
C4—C5—C6	119.9 (3)	C17—C16—H16	120.0
C4—C5—H5	120.0	C18—C17—C16	120.0
C6—C5—H5	120.0	C18—C17—H17	120.0
N1—C6—C1	115.6 (2)	C16—C17—H17	120.0
N1—C6—C5	125.7 (3)	C17—C18—C19	120.0
C1—C6—C5	118.7 (3)	C17—C18—H18	120.0
N1—C7—C9	124.4 (2)	C19—C18—H18	120.0
N1—C7—S1	115.99 (19)	C20—C19—C18	120.0
C9—C7—S1	119.57 (17)	C20—C19—H19	120.0
O1—C8—N3	123.1 (2)	C18—C19—H19	120.0
O1—C8—C9	131.8 (3)	C19—C20—C15	120.0
N3—C8—C9	105.0 (2)	C19—C20—H20	120.0
C10—C9—C8	108.3 (2)	C15—C20—H20	120.0
C10—C9—C7	128.8 (2)	C16'—C15'—C20'	120.0
C8—C9—C7	122.9 (2)	C16'—C15'—N3	111.8 (10)
N2—C10—C9	109.4 (2)	C20'—C15'—N3	125.8 (11)
N2—C10—C11	121.2 (3)	C15'—C16'—C17'	120.0
C9—C10—C11	129.4 (2)	C15'—C16'—H16'	120.0
C10—C11—H11A	109.5	C17'—C16'—H16'	120.0
C10—C11—H11B	109.5	C18'—C17'—C16'	120.0
H11A—C11—H11B	109.5	C18'—C17'—H17'	120.0
C10—C11—H11C	109.5	C16'—C17'—H17'	120.0
H11A—C11—H11C	109.5	C19'—C18'—C17'	120.0
H11B—C11—H11C	109.5	C19'—C18'—H18'	120.0
N2—C12—C13'	112.3 (9)	C17'—C18'—H18'	120.0
N2—C12—C13	107.8 (9)	C18'—C19'—C20'	120.0
N2—C12—H12A	110.1	C18'—C19'—H19'	120.0
C13'—C12—H12A	118.2	C20'—C19'—H19'	120.0
C13—C12—H12A	110.1	C19'—C20'—C15'	120.0
N2—C12—H12B	110.1	C19'—C20'—H20'	120.0
C13—C12—H12B	110.1	C15'—C20'—H20'	120.0

C10—N2—N3—C8	5.6 (3)	C12—N2—C10—C11	13.0 (4)
C12—N2—N3—C8	168.3 (2)	C8—C9—C10—N2	2.0 (3)
C10—N2—N3—C15'	161.9 (8)	C7—C9—C10—N2	179.5 (2)
C12—N2—N3—C15'	−35.5 (8)	C8—C9—C10—C11	−177.2 (3)
C10—N2—N3—C15	168.7 (9)	C7—C9—C10—C11	0.3 (5)
C12—N2—N3—C15	−28.7 (9)	C10—N2—C12—C13'	77.9 (7)
C7—S1—C1—C6	1.10 (18)	N3—N2—C12—C13'	−81.3 (7)
C7—S1—C1—C2	179.7 (2)	C10—N2—C12—C13	64.1 (7)
C6—C1—C2—C3	−0.8 (4)	N3—N2—C12—C13	−95.2 (7)
S1—C1—C2—C3	−179.3 (2)	N2—C12—C13—C14	−142.4 (14)
C1—C2—C3—C4	−0.1 (4)	C13'—C12—C13—C14	106 (7)
C2—C3—C4—C5	0.8 (5)	N2—C12—C13'—C14'	−108 (2)
C3—C4—C5—C6	−0.6 (5)	C13—C12—C13'—C14'	−35 (6)
C7—N1—C6—C1	0.3 (3)	C8—N3—C15—C16	−133.0 (8)
C7—N1—C6—C5	179.4 (3)	N2—N3—C15—C16	65.4 (10)
C2—C1—C6—N1	−179.8 (2)	C15'—N3—C15—C16	91 (6)
S1—C1—C6—N1	−1.1 (3)	C8—N3—C15—C20	60.6 (8)
C2—C1—C6—C5	1.0 (4)	N2—N3—C15—C20	−101.0 (10)
S1—C1—C6—C5	179.8 (2)	C15'—N3—C15—C20	−75 (6)
C4—C5—C6—N1	−179.4 (3)	C20—C15—C16—C17	0.0
C4—C5—C6—C1	−0.3 (4)	N3—C15—C16—C17	−165.3 (9)
C6—N1—C7—C9	−177.2 (2)	C15—C16—C17—C18	0.0
C6—N1—C7—S1	0.6 (3)	C16—C17—C18—C19	0.0
C1—S1—C7—N1	−1.01 (19)	C17—C18—C19—C20	0.0
C1—S1—C7—C9	176.89 (19)	C18—C19—C20—C15	0.0
N2—N3—C8—O1	176.1 (3)	C16—C15—C20—C19	0.0
C15'—N3—C8—O1	23.3 (8)	N3—C15—C20—C19	167.6 (9)
C15—N3—C8—O1	10.8 (7)	C8—N3—C15'—C16'	−121.9 (9)
N2—N3—C8—C9	−4.3 (3)	N2—N3—C15'—C16'	87.4 (7)
C15'—N3—C8—C9	−157.0 (7)	C15—N3—C15'—C16'	−71 (6)
C15—N3—C8—C9	−169.5 (7)	C8—N3—C15'—C20'	40.7 (11)
O1—C8—C9—C10	−178.9 (3)	N2—N3—C15'—C20'	−110.1 (9)
N3—C8—C9—C10	1.4 (3)	C15—N3—C15'—C20'	92 (6)
O1—C8—C9—C7	3.4 (5)	C20'—C15'—C16'—C17'	0.0
N3—C8—C9—C7	−176.2 (2)	N3—C15'—C16'—C17'	163.7 (10)
N1—C7—C9—C10	7.8 (4)	C15'—C16'—C17'—C18'	0.0
S1—C7—C9—C10	−169.9 (2)	C16'—C17'—C18'—C19'	0.0
N1—C7—C9—C8	−175.0 (2)	C17'—C18'—C19'—C20'	0.0
S1—C7—C9—C8	7.2 (3)	C18'—C19'—C20'—C15'	0.0
N3—N2—C10—C9	−4.7 (3)	C16'—C15'—C20'—C19'	0.0
C12—N2—C10—C9	−166.3 (3)	N3—C15'—C20'—C19'	−161.3 (9)
N3—N2—C10—C11	174.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1ⁱ	0.93	2.59	3.318 (3)	135
C12—H12A···O1ⁱⁱ	0.97	2.51	3.404 (4)	152
C12—H12C···O1ⁱⁱ	0.97	2.48	3.404 (4)	159

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₇N₃OS
M_r	347.43
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	17.8734 (5), 10.4297 (2), 18.9578 (4)
V (Å³)	3534.00 (14)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.30 × 0.30 × 0.25

Data collection
Diffractometer	Bruker X8 APEXII
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.944, 0.953
No. of measured, independent and observed [I > 2σ(I)] reflections	18349, 3678, 2341
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.629

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.172, 1.00
No. of reflections	3678
No. of parameters	227
No. of restraints	17
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.25

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O1ⁱ	0.93	2.59	3.318 (3)	135
C12—H12A···O1ⁱⁱ	0.97	2.51	3.404 (4)	152
C12—H12C···O1ⁱⁱ	0.97	2.48	3.404 (4)	159

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

Acknowledgements

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

References

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Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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