Abstract
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,
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[F 2 > 2σ(F 2)] = 0.041
wR(F 2) = 0.109
S = 1.06
4821 reflections
192 parameters
H-atom parameters constrained
Δρmax = 0.58 e Å−3
Δρmin = −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 ▶).
Supplementary Material
Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812000098/bt5773sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812000098/bt5773Isup2.hkl
Supplementary material file. DOI: 10.1107/S1600536812000098/bt5773Isup3.cml
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
Acknowledgments
The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.
supplementary crystallographic information
Comment
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.
Experimental
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
Refinement
The H atoms were positioned geometrically and constrained to ride on their parent atoms with C—H = 0.93Å and Uiso(H) = 1.2 Ueq(C).
The atoms S1 and C8 in the thiophene ring are mutually disordered by a ratio of 0.7706 (19):0.2294 (19).
Figures
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.
Crystal data
| C16H10N2S | F(000) = 544 |
| Mr = 262.32 | Dx = 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
| Bruker APEXII CCD detector diffractometer | 4179 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.034 |
| graphite | θmax = 34.0°, θmin = 2.2° |
| ω and φ scans | h = −10→8 |
| 27721 measured reflections | k = −25→25 |
| 4821 independent reflections | l = −15→18 |
Refinement
| 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(Fo2) + (0.0478P)2 + 0.5714P] where P = (Fo2 + 2Fc2)/3 |
| 4821 reflections | (Δ/σ)max = 0.004 |
| 192 parameters | Δρmax = 0.58 e Å−3 |
| 0 restraints | Δρmin = −0.24 e Å−3 |
Special details
| 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)
| x | y | z | Uiso*/Ueq | 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)
| 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, °)
| 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 |
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5773).
References
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812000098/bt5773sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812000098/bt5773Isup2.hkl
Supplementary material file. DOI: 10.1107/S1600536812000098/bt5773Isup3.cml
Additional supplementary materials: crystallographic information; 3D view; checkCIF report