2-Phenyl­thieno[2,3-b]quinoxaline

Ramli, Y.; Zouihri, H.; Azougagh, M.; Moussaif, A.; Essassi, E.M.

doi:10.1107/S1600536812000098

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o396

doi:10.1107/S1600536812000098

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2-Phenylthieno[2,3-b]quinoxaline

Youssef Ramli,^a,^b ^* Hafid Zouihri,^c Mohamed Azougagh,^a Ahmed Moussaif ^d and El Mokhtar Essassi ^b

^aLaboratoire Nationale de Controle des Medicaments, Direction du Medicament et de la Pharmacie, BP 6206, 10000 Rabat, Morocco, ^bLaboratoire de Chimie Heterocyclique, Pole de Competence PHARCHIM, Université Mohammed V-Agdal, BP 1014, Rabat, Morocco, ^cLaboratoire de Diffraction des Rayons X, Division UATRS, Centre National pour la Recherche Scientifique et Technique, Rabat, Morocco, and ^dUnité de la Radioimmunoanalyse, Centre National d'Etudes Scientifiques et Techniques d'Energie Nucléaire, Maamoura, Morocco
^*Correspondence e-mail: yramli76@yahoo.fr

(Received 28 December 2011; accepted 2 January 2012; online 14 January 2012)

The title compound, C₁₆H₁₀N₂S, is almost planar (r.m.s. deviation for all non-H atoms = 0.080 Å). The dihedral angle between the three fused-ring system and the phenyl ring is 9.26 (3)°. The S atom and the opposite C atom of the thiophene ring are mutually disordered with an occupancy ratio of 0.7706 (19):0.2294 (19).

Related literature

For a related structure, see: Ramli et al. (2011 ). For the biological activity of quinoxaline derivatives, see: Kleim et al. (1995 ). For their antitumour and antituberculous properties, see: Abasolo et al. (1987 ); Rodrigo et al. (2002 ) and for their antifungal, herbicidal, antidyslipidemic and antioxidative activity, see: Jampilek et al. (2005 ); Sashidhara et al. (2009 ); Watkins et al. (2009 ).

Experimental

Crystal data

C₁₆H₁₀N₂S
M_r = 262.32
Monoclinic, P 2₁ /n
a = 6.3875 (3) Å
b = 16.2896 (8) Å
c = 11.6054 (6) Å
β = 96.039 (3)°
V = 1200.84 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 296 K
0.41 × 0.24 × 0.21 mm

Data collection

Bruker APEXII CCD detector diffractometer
27721 measured reflections
4821 independent reflections
4179 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.109
S = 1.06
4821 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812000098/bt5773sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812000098/bt5773Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812000098/bt5773Isup3.cml

checkCIF report

Comment top

Quinoxaline derivatives were found to exhibit antimicrobial [Kleim et al. 1995], antitumor [Abasolo et al. 1987], and antituberculous activity [Rodrigo et al.2002]. They, also, exhibit interesting antifungal, herbicidal, Antidyslipidemic and antioxidative activities of quinoxaline derivatives, see: [Jampilek et al. 2005, Sashidhara et al. 2009, Watkins et al. 2009].

In a former paper, we reported the crystal structure of 2-Methyl-3-(n-octylsulfanyl)quinoxaline [Ramli et al. 2011]. In this communication, the crystal structure of 2-phenyl-4a,8a-dihydrothieno[2,3-b]quinoxaline.

The title compound, C₁₆H₁₀N₂S, shows an almost planar geometry, defined by the attached benzene [r.m.s. deviation: 0.0089 (10) A] and 4a,8a-dihydrothieno[2,3-b]quinoxaline groups [r.m.s. deviation: 0.2722 (9) A]. The dihedral angle between the planes of this groups is 9.26 (3)°. The S1 and C9 atoms of the thiophene ring displays 0.7706 (19): 0.2294 (19) positional disorder.

Related literature top

For a related structure, see: Ramli et al. (2011). For the biological activity of quinoxaline derivatives, see: Kleim et al. (1995). For their antitumour and antituberculous properties, see: Abasolo et al. (1987); Rodrigo et al. (2002) and for their antifungal, herbicidal, antidyslipidemic and antioxidative activity, see: Jampilek et al. (2005); Sashidhara et al. (2009); Watkins et al. (2009).

Experimental top

6.25 mmol of 3-methylquinoxaline-2-thione is merged with 12.5 mmol of the appropriate aldehyde for 2 h at the boiling point of the latter. At the end of the reaction, the solid is allowed to cool and then heated to 100° C for 10 minutes in 50 ml of ethanol. The product is filtered hot and washed with ethanol

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Molecular view of the title compound showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.

2-Phenylthieno[2,3-b]quinoxaline top

Crystal data top

C₁₆H₁₀N₂S	F(000) = 544
M_r = 262.32	D_x = 1.451 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 215 reflections
a = 6.3875 (3) Å	θ = 1.8–26.7°
b = 16.2896 (8) Å	µ = 0.25 mm⁻¹
c = 11.6054 (6) Å	T = 296 K
β = 96.039 (3)°	Prism, yellow
V = 1200.84 (10) Å³	0.41 × 0.24 × 0.21 mm
Z = 4

Data collection top

Bruker APEXII CCD detector diffractometer	4179 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.034
Graphite monochromator	θ_max = 34.0°, θ_min = 2.2°
ω and ϕ scans	h = −10→8
27721 measured reflections	k = −25→25
4821 independent reflections	l = −15→18

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0478P)² + 0.5714P] where P = (F_o² + 2F_c²)/3
4821 reflections	(Δ/σ)_max = 0.004
192 parameters	Δρ_max = 0.58 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₆H₁₀N₂S	V = 1200.84 (10) Å³
M_r = 262.32	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.3875 (3) Å	µ = 0.25 mm⁻¹
b = 16.2896 (8) Å	T = 296 K
c = 11.6054 (6) Å	0.41 × 0.24 × 0.21 mm
β = 96.039 (3)°

Data collection top

Bruker APEXII CCD detector diffractometer	4179 reflections with I > 2σ(I)
27721 measured reflections	R_int = 0.034
4821 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 1.06	Δρ_max = 0.58 e Å⁻³
4821 reflections	Δρ_min = −0.24 e Å⁻³
192 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	Occ. (<1)
S1A	0.54001 (5)	0.93619 (2)	0.62771 (5)	0.01314 (11)	0.7706 (19)
C1	0.90893 (16)	1.05183 (6)	0.61903 (9)	0.01554 (17)
H1	0.8109	1.0383	0.5569	0.019*
C6	0.87615 (15)	1.02638 (6)	0.73110 (8)	0.01308 (16)
C5	1.02452 (16)	1.04876 (6)	0.82349 (9)	0.01653 (18)
H5	1.0041	1.0331	0.8986	0.020*
C7	0.69078 (15)	0.97700 (6)	0.75084 (8)	0.01331 (17)
C4	1.20213 (17)	1.09414 (6)	0.80401 (10)	0.01888 (19)
H4	1.2993	1.1088	0.8660	0.023*
C2	1.08669 (17)	1.09714 (6)	0.59971 (10)	0.01815 (19)
H2	1.1066	1.1138	0.5250	0.022*
C3	1.23453 (17)	1.11763 (6)	0.69180 (10)	0.01883 (19)
H3	1.3547	1.1469	0.6786	0.023*
C10	0.14188 (16)	0.83199 (6)	0.87817 (8)	0.01446 (17)
C15	0.08412 (15)	0.82081 (6)	0.75707 (8)	0.01349 (16)
C9	0.42799 (16)	0.90599 (6)	0.83950 (10)	0.01732 (18)
C14	−0.10173 (16)	0.77645 (6)	0.71932 (9)	0.01765 (19)
H14	−0.1401	0.7688	0.6405	0.021*
C16	0.36948 (16)	0.89267 (6)	0.71805 (9)	0.01666 (18)
C11	0.01306 (17)	0.79725 (7)	0.95760 (9)	0.01880 (19)
H11	0.0504	0.8032	1.0368	0.023*
C12	−0.16630 (18)	0.75488 (7)	0.91879 (11)	0.0211 (2)
H12	−0.2500	0.7326	0.9718	0.025*
C13	−0.22485 (17)	0.74484 (6)	0.79834 (11)	0.0205 (2)
H13	−0.3476	0.7166	0.7728	0.025*
N2	0.20272 (14)	0.85147 (5)	0.67565 (8)	0.01643 (16)
N1	0.31701 (15)	0.87565 (6)	0.91971 (8)	0.01824 (17)
C8A	0.6155 (2)	0.95601 (9)	0.8506 (2)	0.0156 (3)	0.7706 (19)
H8A	0.6801	0.9727	0.9223	0.019*	0.7706 (19)
S1B	0.6418 (2)	0.96348 (8)	0.89788 (17)	0.0172 (4)	0.2294 (19)
C8B	0.5408 (8)	0.9415 (3)	0.6794 (7)	0.0181 (9)	0.2294 (19)
H8B	0.5454	0.9481	0.6002	0.022*	0.2294 (19)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1A	0.01306 (14)	0.01609 (14)	0.0103 (2)	−0.00218 (10)	0.00130 (12)	0.00077 (12)
C1	0.0167 (4)	0.0156 (4)	0.0146 (4)	0.0001 (3)	0.0033 (3)	−0.0008 (3)
C6	0.0123 (4)	0.0128 (3)	0.0144 (4)	0.0005 (3)	0.0020 (3)	−0.0005 (3)
C5	0.0156 (4)	0.0175 (4)	0.0162 (4)	−0.0015 (3)	0.0000 (3)	0.0002 (3)
C7	0.0127 (4)	0.0139 (3)	0.0132 (4)	0.0002 (3)	0.0005 (3)	0.0000 (3)
C4	0.0154 (4)	0.0179 (4)	0.0229 (5)	−0.0021 (3)	0.0001 (4)	−0.0012 (3)
C2	0.0199 (4)	0.0162 (4)	0.0197 (5)	−0.0003 (3)	0.0081 (4)	0.0001 (3)
C3	0.0159 (4)	0.0146 (4)	0.0268 (5)	−0.0009 (3)	0.0062 (4)	−0.0016 (3)
C10	0.0148 (4)	0.0150 (4)	0.0137 (4)	0.0015 (3)	0.0019 (3)	0.0004 (3)
C15	0.0137 (4)	0.0134 (3)	0.0134 (4)	0.0003 (3)	0.0016 (3)	0.0015 (3)
C9	0.0133 (4)	0.0158 (4)	0.0221 (5)	0.0005 (3)	−0.0012 (3)	−0.0012 (3)
C14	0.0165 (4)	0.0164 (4)	0.0193 (5)	−0.0014 (3)	−0.0018 (3)	0.0013 (3)
C16	0.0149 (4)	0.0162 (4)	0.0197 (5)	0.0023 (3)	0.0057 (3)	0.0051 (3)
C11	0.0207 (5)	0.0209 (4)	0.0157 (4)	0.0037 (4)	0.0059 (4)	0.0033 (3)
C12	0.0190 (5)	0.0192 (4)	0.0268 (5)	0.0024 (4)	0.0103 (4)	0.0071 (4)
C13	0.0151 (4)	0.0161 (4)	0.0300 (6)	−0.0019 (3)	0.0012 (4)	0.0035 (4)
N2	0.0175 (4)	0.0173 (4)	0.0149 (4)	0.0016 (3)	0.0037 (3)	0.0027 (3)
N1	0.0170 (4)	0.0197 (4)	0.0175 (4)	0.0008 (3)	−0.0009 (3)	−0.0023 (3)
C8A	0.0148 (6)	0.0193 (6)	0.0120 (7)	−0.0013 (4)	−0.0015 (5)	−0.0012 (5)
S1B	0.0150 (5)	0.0205 (5)	0.0160 (8)	−0.0038 (4)	0.0006 (5)	0.0002 (5)
C8B	0.022 (2)	0.023 (2)	0.008 (2)	0.0030 (16)	0.0028 (19)	−0.0009 (18)

Geometric parameters (Å, º) top

S1A—C16	1.7403 (11)	C10—C15	1.4267 (14)
S1A—C7	1.7669 (10)	C15—N2	1.3663 (13)
C1—C2	1.3921 (15)	C15—C14	1.4192 (14)
C1—C6	1.4017 (14)	C9—N1	1.3236 (15)
C1—H1	0.9300	C9—C16	1.4362 (15)
C6—C5	1.4024 (14)	C9—C8A	1.4430 (19)
C6—C7	1.4692 (14)	C9—S1B	1.7338 (18)
C5—C4	1.3923 (15)	C14—C13	1.3698 (16)
C5—H5	0.9300	C14—H14	0.9300
C7—C8B	1.331 (7)	C16—N2	1.3103 (14)
C7—C8A	1.344 (2)	C16—C8B	1.460 (6)
C7—S1B	1.781 (2)	C11—C12	1.3722 (16)
C4—C3	1.3935 (16)	C11—H11	0.9300
C4—H4	0.9300	C12—C13	1.4179 (17)
C2—C3	1.3903 (16)	C12—H12	0.9300
C2—H2	0.9300	C13—H13	0.9300
C3—H3	0.9300	C8A—H8A	0.9300
C10—N1	1.3697 (13)	C8B—H8B	0.9300
C10—C11	1.4165 (14)

C16—S1A—C7	89.34 (5)	C14—C15—C10	119.36 (9)
C2—C1—C6	120.68 (9)	N1—C9—C16	122.04 (9)
C2—C1—H1	119.7	N1—C9—C8A	130.45 (13)
C6—C1—H1	119.7	C16—C9—C8A	107.50 (12)
C1—C6—C5	118.53 (9)	N1—C9—S1B	112.64 (10)
C1—C6—C7	120.54 (9)	C16—C9—S1B	125.31 (10)
C5—C6—C7	120.93 (9)	C8A—C9—S1B	17.82 (8)
C4—C5—C6	120.70 (10)	C13—C14—C15	120.34 (10)
C4—C5—H5	119.7	C13—C14—H14	119.8
C6—C5—H5	119.7	C15—C14—H14	119.8
C8B—C7—C8A	97.3 (3)	N2—C16—C9	124.28 (9)
C8B—C7—C6	132.8 (3)	N2—C16—C8B	140.3 (3)
C8A—C7—C6	129.87 (12)	C9—C16—C8B	95.3 (3)
C8B—C7—S1A	15.8 (3)	N2—C16—S1A	121.20 (8)
C8A—C7—S1A	112.77 (10)	C9—C16—S1A	114.52 (8)
C6—C7—S1A	117.35 (7)	C8B—C16—S1A	19.4 (3)
C8B—C7—S1B	110.8 (3)	C12—C11—C10	120.63 (10)
C8A—C7—S1B	13.58 (8)	C12—C11—H11	119.7
C6—C7—S1B	116.29 (8)	C10—C11—H11	119.7
S1A—C7—S1B	126.35 (7)	C11—C12—C13	120.40 (10)
C5—C4—C3	120.08 (10)	C11—C12—H12	119.8
C5—C4—H4	120.0	C13—C12—H12	119.8
C3—C4—H4	120.0	C14—C13—C12	120.42 (10)
C3—C2—C1	120.20 (10)	C14—C13—H13	119.8
C3—C2—H2	119.9	C12—C13—H13	119.8
C1—C2—H2	119.9	C16—N2—C15	114.55 (9)
C2—C3—C4	119.79 (10)	C9—N1—C10	115.11 (9)
C2—C3—H3	120.1	C7—C8A—C9	115.82 (17)
C4—C3—H3	120.1	C7—C8A—H8A	122.1
N1—C10—C11	119.16 (9)	C9—C8A—H8A	122.1
N1—C10—C15	122.00 (9)	C9—S1B—C7	84.43 (10)
C11—C10—C15	118.84 (9)	C7—C8B—C16	124.0 (6)
N2—C15—C14	118.63 (9)	C7—C8B—H8B	118.0
N2—C15—C10	122.00 (9)	C16—C8B—H8B	118.0

Experimental details

Crystal data
Chemical formula	C₁₆H₁₀N₂S
M_r	262.32
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	6.3875 (3), 16.2896 (8), 11.6054 (6)
β (°)	96.039 (3)
V (Å³)	1200.84 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.41 × 0.24 × 0.21

Data collection
Diffractometer	Bruker APEXII CCD detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	27721, 4821, 4179
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.787

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.109, 1.06
No. of reflections	4821
No. of parameters	192
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.24

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), publCIF (Westrip, 2010).

Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.

References

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