Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807060783/cs2062sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807060783/cs2062Isup2.hkl |
CCDC reference: 673059
Key indicators
- Single-crystal X-ray study
- T = 200 K
- Mean (C-C) = 0.002 Å
- R factor = 0.043
- wR factor = 0.125
- Data-to-parameter ratio = 21.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.97 PLAT230_ALERT_2_C Hirshfeld Test Diff for F1 - C51 .. 5.82 su PLAT230_ALERT_2_C Hirshfeld Test Diff for N5 - C12 .. 6.28 su PLAT431_ALERT_2_C Short Inter HL..A Contact F2 .. N5 .. 2.98 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact O1 .. C5 .. 3.01 Ang.
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.972 Tmax scaled 0.972 Tmin scaled 0.874
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For the uses of [1,2,4]triazoloquinoxalines, see Ali et al. (2004); Bicking (1959); Chimirri et al. (2002); Dawood et al. (2006); Ilkay et al. (2004); Potts (1961); Trivedi (1988); Xie et al. (2005).
To a mixture of compounds 4-methyl-1-(trifluoromethyl)[1,2,4]triazolo[4,3-a]quinoxaline (5.0 g, 0.0198 mol), and 2-nitrobenzaldehyde (3.14 g, 0.0208 mol) in methanol (20 ml) added catalytic amount (0.2 ml) of conc. sulfuric acid. The reaction mass was refluxed (338 K) for 8 h. The reaction mass was cooled to room temperature, and kept overnight. The separated solid was filtered, washed with methanol (5 ml) to obtain the title compound. The compound was further recrystalized from ethanol to give pale yellow crystals 4.0 g, 52.6%.
H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.95 Å and Uiso = 1.2 times Ueq(C).
Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis CCD (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003).
C18H10F3N5O2 | F(000) = 784 |
Mr = 385.31 | Dx = 1.575 Mg m−3 |
Monoclinic, P21/n | Melting point: 472(1) K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 8.0065 (2) Å | Cell parameters from 6025 reflections |
b = 16.9010 (4) Å | θ = 4.8–32.5° |
c = 12.0204 (3) Å | µ = 0.13 mm−1 |
β = 92.633 (2)° | T = 200 K |
V = 1624.86 (7) Å3 | Prism, pale yellow |
Z = 4 | 0.37 × 0.35 × 0.22 mm |
Oxford Diffraction Gemini diffractometer | 5345 independent reflections |
Radiation source: fine-focus sealed tube | 3157 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
Detector resolution: 10.5081 pixels mm-1 | θmax = 32.6°, θmin = 4.8° |
ϕ and ω scans | h = −11→11 |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | k = −25→25 |
Tmin = 0.899, Tmax = 1.000 | l = −17→17 |
15678 measured reflections |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.125 | H-atom parameters constrained |
S = 0.98 | w = 1/[σ2(Fo2) + (0.0729P)2] where P = (Fo2 + 2Fc2)/3 |
5345 reflections | (Δ/σ)max = 0.001 |
253 parameters | Δρmax = 0.35 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
C18H10F3N5O2 | V = 1624.86 (7) Å3 |
Mr = 385.31 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.0065 (2) Å | µ = 0.13 mm−1 |
b = 16.9010 (4) Å | T = 200 K |
c = 12.0204 (3) Å | 0.37 × 0.35 × 0.22 mm |
β = 92.633 (2)° |
Oxford Diffraction Gemini diffractometer | 5345 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | 3157 reflections with I > 2σ(I) |
Tmin = 0.899, Tmax = 1.000 | Rint = 0.023 |
15678 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.125 | H-atom parameters constrained |
S = 0.98 | Δρmax = 0.35 e Å−3 |
5345 reflections | Δρmin = −0.28 e Å−3 |
253 parameters |
x | y | z | Uiso*/Ueq | ||
F1 | 0.33806 (11) | 0.79608 (5) | 0.83090 (7) | 0.0536 (3) | |
F2 | 0.56207 (10) | 0.81556 (5) | 0.74471 (7) | 0.0473 (3) | |
F3 | 0.33485 (13) | 0.87452 (5) | 0.69060 (8) | 0.0638 (4) | |
O1 | 0.30844 (12) | 0.28804 (5) | 0.43450 (8) | 0.0420 (3) | |
O2 | 0.12053 (14) | 0.20138 (6) | 0.38762 (11) | 0.0588 (4) | |
N1 | 0.26886 (14) | 0.75604 (6) | 0.55632 (9) | 0.0381 (3) | |
N2 | 0.23975 (14) | 0.68574 (6) | 0.50247 (9) | 0.0359 (3) | |
N4 | 0.37684 (11) | 0.66121 (6) | 0.66443 (7) | 0.0253 (3) | |
N4A | 0.37242 (12) | 0.49810 (6) | 0.62414 (8) | 0.0293 (3) | |
N5 | 0.17977 (14) | 0.26776 (6) | 0.38229 (9) | 0.0367 (3) | |
C1 | 0.22162 (15) | 0.51486 (7) | 0.44843 (10) | 0.0302 (3) | |
C2 | 0.17674 (14) | 0.43913 (7) | 0.43653 (9) | 0.0290 (3) | |
C3 | 0.30453 (14) | 0.63014 (7) | 0.56780 (9) | 0.0268 (3) | |
C3A | 0.30274 (14) | 0.54560 (7) | 0.55073 (9) | 0.0274 (3) | |
C4A | 0.45134 (14) | 0.52974 (7) | 0.71888 (9) | 0.0266 (3) | |
C5 | 0.34938 (15) | 0.74113 (7) | 0.65139 (10) | 0.0305 (3) | |
C5A | 0.53147 (15) | 0.47701 (7) | 0.79337 (10) | 0.0329 (3) | |
C6 | 0.61637 (17) | 0.50386 (8) | 0.88796 (11) | 0.0384 (4) | |
C7 | 0.62241 (16) | 0.58451 (8) | 0.91106 (10) | 0.0373 (4) | |
C8 | 0.54455 (15) | 0.63835 (7) | 0.84044 (10) | 0.0314 (3) | |
C8A | 0.45896 (14) | 0.61160 (7) | 0.74388 (9) | 0.0254 (3) | |
C11 | 0.09609 (14) | 0.40639 (7) | 0.33468 (9) | 0.0283 (3) | |
C12 | 0.09491 (15) | 0.32572 (7) | 0.30827 (10) | 0.0298 (3) | |
C13 | 0.01979 (17) | 0.29588 (8) | 0.21091 (12) | 0.0400 (4) | |
C14 | −0.05853 (17) | 0.34677 (9) | 0.13569 (11) | 0.0447 (5) | |
C15 | −0.06427 (16) | 0.42677 (9) | 0.16040 (11) | 0.0416 (4) | |
C16 | 0.01072 (16) | 0.45550 (8) | 0.25819 (10) | 0.0342 (4) | |
C51 | 0.39666 (17) | 0.80652 (7) | 0.72976 (12) | 0.0389 (4) | |
H1 | 0.19990 | 0.55012 | 0.38794 | 0.0362* | |
H2 | 0.19835 | 0.40442 | 0.49767 | 0.0348* | |
H5 | 0.52718 | 0.42184 | 0.77840 | 0.0395* | |
H6 | 0.67091 | 0.46736 | 0.93754 | 0.0460* | |
H7 | 0.68122 | 0.60262 | 0.97662 | 0.0448* | |
H8 | 0.54894 | 0.69326 | 0.85719 | 0.0377* | |
H13 | 0.02229 | 0.24068 | 0.19614 | 0.0479* | |
H14 | −0.10796 | 0.32725 | 0.06776 | 0.0536* | |
H15 | −0.12013 | 0.46215 | 0.10981 | 0.0499* | |
H16 | 0.00385 | 0.51049 | 0.27373 | 0.0410* |
U11 | U22 | U33 | U12 | U13 | U23 | |
F1 | 0.0648 (5) | 0.0496 (5) | 0.0472 (5) | −0.0069 (4) | 0.0121 (4) | −0.0219 (4) |
F2 | 0.0486 (5) | 0.0391 (4) | 0.0534 (5) | −0.0125 (4) | −0.0049 (4) | −0.0113 (4) |
F3 | 0.0897 (7) | 0.0208 (4) | 0.0781 (7) | 0.0094 (4) | −0.0264 (5) | −0.0086 (4) |
O1 | 0.0420 (5) | 0.0355 (5) | 0.0478 (5) | 0.0043 (4) | −0.0047 (4) | 0.0018 (4) |
O2 | 0.0655 (7) | 0.0227 (5) | 0.0879 (9) | −0.0070 (5) | 0.0008 (6) | 0.0064 (5) |
N1 | 0.0484 (6) | 0.0241 (5) | 0.0409 (6) | −0.0006 (5) | −0.0084 (5) | 0.0002 (5) |
N2 | 0.0488 (6) | 0.0237 (5) | 0.0341 (6) | −0.0012 (5) | −0.0103 (5) | 0.0006 (4) |
N4 | 0.0307 (5) | 0.0203 (4) | 0.0247 (5) | −0.0019 (4) | −0.0022 (4) | −0.0026 (4) |
N4A | 0.0371 (5) | 0.0229 (5) | 0.0274 (5) | −0.0029 (4) | −0.0027 (4) | −0.0029 (4) |
N5 | 0.0404 (6) | 0.0237 (5) | 0.0463 (6) | 0.0003 (5) | 0.0047 (5) | −0.0019 (5) |
C1 | 0.0384 (6) | 0.0245 (6) | 0.0271 (6) | −0.0013 (5) | −0.0054 (5) | −0.0024 (5) |
C2 | 0.0333 (6) | 0.0246 (6) | 0.0286 (6) | 0.0011 (5) | −0.0041 (5) | −0.0025 (5) |
C3 | 0.0325 (6) | 0.0231 (5) | 0.0245 (5) | −0.0032 (4) | −0.0025 (4) | −0.0025 (4) |
C3A | 0.0336 (6) | 0.0229 (5) | 0.0254 (5) | −0.0038 (5) | −0.0008 (4) | −0.0032 (5) |
C4A | 0.0302 (6) | 0.0232 (5) | 0.0262 (5) | −0.0029 (4) | −0.0012 (4) | −0.0018 (5) |
C5 | 0.0371 (6) | 0.0191 (5) | 0.0350 (6) | −0.0008 (5) | −0.0021 (5) | −0.0028 (5) |
C5A | 0.0407 (7) | 0.0224 (5) | 0.0352 (6) | −0.0005 (5) | −0.0039 (5) | 0.0015 (5) |
C6 | 0.0456 (7) | 0.0337 (7) | 0.0348 (7) | −0.0012 (6) | −0.0089 (5) | 0.0066 (6) |
C7 | 0.0450 (7) | 0.0357 (7) | 0.0303 (6) | −0.0068 (6) | −0.0088 (5) | −0.0007 (6) |
C8 | 0.0406 (6) | 0.0258 (6) | 0.0274 (6) | −0.0054 (5) | −0.0026 (5) | −0.0033 (5) |
C8A | 0.0282 (5) | 0.0225 (5) | 0.0254 (5) | −0.0011 (4) | −0.0008 (4) | 0.0007 (4) |
C11 | 0.0308 (5) | 0.0238 (5) | 0.0298 (6) | −0.0033 (5) | −0.0031 (4) | −0.0040 (5) |
C12 | 0.0294 (5) | 0.0249 (5) | 0.0348 (6) | −0.0022 (5) | 0.0000 (5) | −0.0037 (5) |
C13 | 0.0411 (7) | 0.0326 (7) | 0.0461 (8) | −0.0078 (6) | 0.0007 (6) | −0.0147 (6) |
C14 | 0.0470 (8) | 0.0505 (9) | 0.0356 (7) | −0.0107 (7) | −0.0093 (6) | −0.0149 (7) |
C15 | 0.0406 (7) | 0.0480 (8) | 0.0350 (7) | −0.0018 (6) | −0.0114 (5) | −0.0014 (6) |
C16 | 0.0386 (7) | 0.0266 (6) | 0.0364 (6) | −0.0002 (5) | −0.0094 (5) | −0.0015 (5) |
C51 | 0.0478 (8) | 0.0216 (6) | 0.0465 (8) | −0.0012 (5) | −0.0051 (6) | −0.0048 (6) |
F1—C51 | 1.3348 (17) | C5A—C6 | 1.3747 (18) |
F2—C51 | 1.3370 (16) | C6—C7 | 1.3915 (19) |
F3—C51 | 1.3289 (15) | C7—C8 | 1.3743 (18) |
O1—N5 | 1.2301 (15) | C8—C8A | 1.3958 (16) |
O2—N5 | 1.2209 (15) | C11—C12 | 1.3998 (17) |
N1—N2 | 1.3679 (15) | C11—C16 | 1.3942 (17) |
N1—C5 | 1.3105 (16) | C12—C13 | 1.3860 (19) |
N2—C3 | 1.3158 (16) | C13—C14 | 1.378 (2) |
N4—C3 | 1.3778 (14) | C14—C15 | 1.386 (2) |
N4—C5 | 1.3763 (16) | C15—C16 | 1.3832 (18) |
N4—C8A | 1.4106 (14) | C1—H1 | 0.9500 |
N4A—C3A | 1.2997 (15) | C2—H2 | 0.9500 |
N4A—C4A | 1.3842 (15) | C5A—H5 | 0.9500 |
N5—C12 | 1.4688 (16) | C6—H6 | 0.9500 |
C1—C2 | 1.3353 (17) | C7—H7 | 0.9500 |
C1—C3A | 1.4596 (16) | C8—H8 | 0.9500 |
C2—C11 | 1.4661 (16) | C13—H13 | 0.9500 |
C3—C3A | 1.4435 (17) | C14—H14 | 0.9500 |
C4A—C5A | 1.3981 (16) | C15—H15 | 0.9500 |
C4A—C8A | 1.4165 (17) | C16—H16 | 0.9500 |
C5—C51 | 1.4898 (18) | ||
F1···N4 | 3.0583 (13) | C3A···C16i | 3.4791 (17) |
F1···C8 | 3.1362 (15) | C4A···C1iii | 3.4573 (16) |
F1···C13i | 3.2779 (16) | C4A···C15i | 3.5586 (17) |
F1···O1ii | 3.1065 (13) | C5···O1iii | 3.0124 (15) |
F1···C14i | 3.3289 (17) | C5···C13i | 3.5096 (18) |
F2···O2iii | 3.0727 (14) | C5A···O2viii | 3.2875 (16) |
F2···C8 | 3.2139 (15) | C5A···C1iii | 3.5921 (17) |
F2···N4 | 3.1312 (13) | C6···C16iii | 3.5992 (19) |
F2···N5iii | 2.9792 (14) | C6···C6ix | 3.3475 (19) |
F2···O1iii | 2.9977 (12) | C6···C7ix | 3.4852 (18) |
F3···C16iv | 3.2850 (16) | C7···C6ix | 3.4852 (18) |
F3···N1 | 2.6107 (14) | C7···N1iv | 3.3909 (17) |
F1···H8 | 2.4300 | C8···F1 | 3.1362 (15) |
F1···H2ii | 2.7800 | C8···C51 | 3.3325 (17) |
F2···H8 | 2.4700 | C8···C12iii | 3.5173 (17) |
F3···H7v | 2.8300 | C8···F2 | 3.2139 (15) |
F3···H16iv | 2.5500 | C8A···C15i | 3.4734 (17) |
O1···C2 | 2.7633 (15) | C8A···O1iii | 3.3630 (15) |
O1···N4iii | 2.9622 (13) | C11···C3i | 3.5198 (16) |
O1···F1vi | 3.1065 (13) | C12···C8iii | 3.5173 (17) |
O1···F2iii | 2.9977 (12) | C13···C5i | 3.5096 (18) |
O1···C8Aiii | 3.3630 (15) | C13···F1i | 3.2779 (16) |
O1···C3iii | 3.3946 (15) | C14···F1i | 3.3289 (17) |
O1···C5iii | 3.0124 (15) | C15···C8Ai | 3.4734 (17) |
O2···F2iii | 3.0727 (14) | C15···C4Ai | 3.5586 (17) |
O2···C5Avii | 3.2875 (16) | C16···C3Ai | 3.4791 (17) |
O1···H2 | 2.3000 | C16···C6iii | 3.5992 (19) |
O1···H14viii | 2.5900 | C16···F3v | 3.2850 (16) |
O2···H13 | 2.4900 | C51···C8 | 3.3325 (17) |
O2···H5vii | 2.5600 | C1···H16 | 2.6700 |
N1···F3 | 2.6107 (14) | C5···H8 | 2.9900 |
N1···N4 | 2.2140 (14) | C16···H1 | 2.6600 |
N1···C7v | 3.3909 (17) | C51···H8 | 2.7100 |
N2···N4 | 2.2295 (14) | H1···N2 | 2.6900 |
N4···O1iii | 2.9622 (13) | H1···C16 | 2.6600 |
N4···N1 | 2.2140 (14) | H1···H16 | 2.1400 |
N4···F1 | 3.0583 (13) | H2···O1 | 2.3000 |
N4···F2 | 3.1312 (13) | H2···N4A | 2.5600 |
N4···N4A | 2.7989 (14) | H2···N5 | 2.6900 |
N4A···N4 | 2.7989 (14) | H2···F1vi | 2.7800 |
N4A···C1iii | 3.4109 (15) | H5···O2viii | 2.5600 |
N5···F2iii | 2.9792 (14) | H7···F3iv | 2.8300 |
N1···H7v | 2.6600 | H7···N1iv | 2.6600 |
N2···H1 | 2.6900 | H8···F1 | 2.4300 |
N4A···H2 | 2.5600 | H8···F2 | 2.4700 |
N5···H2 | 2.6900 | H8···C5 | 2.9900 |
C1···C5Aiii | 3.5921 (17) | H8···C51 | 2.7100 |
C1···N4Aiii | 3.4109 (15) | H13···O2 | 2.4900 |
C1···C4Aiii | 3.4573 (16) | H14···O1vii | 2.5900 |
C2···O1 | 2.7633 (15) | H16···C1 | 2.6700 |
C3···C11i | 3.5198 (16) | H16···H1 | 2.1400 |
C3···O1iii | 3.3946 (15) | H16···F3v | 2.5500 |
N2—N1—C5 | 108.18 (10) | N5—C12—C11 | 120.94 (10) |
N1—N2—C3 | 106.50 (10) | N5—C12—C13 | 116.07 (11) |
C3—N4—C5 | 102.67 (9) | C11—C12—C13 | 122.96 (11) |
C3—N4—C8A | 120.60 (10) | C12—C13—C14 | 119.59 (12) |
C5—N4—C8A | 136.68 (10) | C13—C14—C15 | 119.15 (13) |
C3A—N4A—C4A | 119.04 (10) | C14—C15—C16 | 120.49 (13) |
O1—N5—O2 | 123.20 (11) | C11—C16—C15 | 122.14 (12) |
O1—N5—C12 | 118.46 (10) | F1—C51—F2 | 106.27 (11) |
O2—N5—C12 | 118.34 (11) | F1—C51—F3 | 107.23 (11) |
C2—C1—C3A | 122.59 (11) | F1—C51—C5 | 112.84 (10) |
C1—C2—C11 | 123.87 (11) | F2—C51—F3 | 107.41 (10) |
N2—C3—N4 | 111.70 (10) | F2—C51—C5 | 113.02 (11) |
N2—C3—C3A | 128.39 (10) | F3—C51—C5 | 109.75 (11) |
N4—C3—C3A | 119.88 (10) | C2—C1—H1 | 119.00 |
N4A—C3A—C1 | 120.84 (11) | C3A—C1—H1 | 119.00 |
N4A—C3A—C3 | 120.92 (10) | C1—C2—H2 | 118.00 |
C1—C3A—C3 | 118.24 (10) | C11—C2—H2 | 118.00 |
N4A—C4A—C5A | 117.35 (10) | C4A—C5A—H5 | 120.00 |
N4A—C4A—C8A | 124.43 (10) | C6—C5A—H5 | 120.00 |
C5A—C4A—C8A | 118.21 (10) | C5A—C6—H6 | 120.00 |
N1—C5—N4 | 110.96 (10) | C7—C6—H6 | 120.00 |
N1—C5—C51 | 120.62 (11) | C6—C7—H7 | 120.00 |
N4—C5—C51 | 128.42 (11) | C8—C7—H7 | 120.00 |
C4A—C5A—C6 | 120.94 (11) | C7—C8—H8 | 120.00 |
C5A—C6—C7 | 119.98 (12) | C8A—C8—H8 | 120.00 |
C6—C7—C8 | 120.98 (12) | C12—C13—H13 | 120.00 |
C7—C8—C8A | 119.38 (11) | C14—C13—H13 | 120.00 |
N4—C8A—C4A | 115.01 (10) | C13—C14—H14 | 120.00 |
N4—C8A—C8 | 124.49 (11) | C15—C14—H14 | 120.00 |
C4A—C8A—C8 | 120.50 (10) | C14—C15—H15 | 120.00 |
C2—C11—C12 | 123.72 (10) | C16—C15—H15 | 120.00 |
C2—C11—C16 | 120.65 (11) | C11—C16—H16 | 119.00 |
C12—C11—C16 | 115.61 (11) | C15—C16—H16 | 119.00 |
C5—N1—N2—C3 | 0.00 (15) | N2—C3—C3A—C1 | 0.73 (18) |
N2—N1—C5—N4 | 0.03 (14) | N4—C3—C3A—N4A | −1.80 (17) |
N2—N1—C5—C51 | −179.10 (11) | N4—C3—C3A—C1 | 178.63 (10) |
N1—N2—C3—N4 | −0.06 (14) | N4A—C4A—C5A—C6 | 178.31 (11) |
N1—N2—C3—C3A | 177.98 (11) | C8A—C4A—C5A—C6 | −0.44 (18) |
C5—N4—C3—N2 | 0.08 (13) | N4A—C4A—C8A—N4 | 0.71 (16) |
C5—N4—C3—C3A | −178.15 (10) | N4A—C4A—C8A—C8 | −178.61 (11) |
C8A—N4—C3—N2 | −177.62 (10) | C5A—C4A—C8A—N4 | 179.36 (10) |
C8A—N4—C3—C3A | 4.16 (15) | C5A—C4A—C8A—C8 | 0.04 (17) |
C3—N4—C5—N1 | −0.07 (13) | N1—C5—C51—F1 | 123.92 (13) |
C3—N4—C5—C51 | 178.98 (12) | N1—C5—C51—F2 | −115.47 (13) |
C8A—N4—C5—N1 | 177.04 (12) | N1—C5—C51—F3 | 4.40 (17) |
C8A—N4—C5—C51 | −3.9 (2) | N4—C5—C51—F1 | −55.05 (17) |
C3—N4—C8A—C4A | −3.52 (15) | N4—C5—C51—F2 | 65.57 (17) |
C3—N4—C8A—C8 | 175.77 (11) | N4—C5—C51—F3 | −174.56 (11) |
C5—N4—C8A—C4A | 179.76 (12) | C4A—C5A—C6—C7 | 0.45 (19) |
C5—N4—C8A—C8 | −1.0 (2) | C5A—C6—C7—C8 | −0.1 (2) |
C4A—N4A—C3A—C1 | 178.55 (10) | C6—C7—C8—C8A | −0.33 (19) |
C4A—N4A—C3A—C3 | −1.01 (16) | C7—C8—C8A—N4 | −178.92 (11) |
C3A—N4A—C4A—C5A | −177.11 (11) | C7—C8—C8A—C4A | 0.34 (17) |
C3A—N4A—C4A—C8A | 1.56 (17) | C2—C11—C12—N5 | −1.24 (18) |
O1—N5—C12—C11 | −33.51 (17) | C2—C11—C12—C13 | −179.18 (12) |
O1—N5—C12—C13 | 144.57 (12) | C16—C11—C12—N5 | −179.76 (11) |
O2—N5—C12—C11 | 147.64 (12) | C16—C11—C12—C13 | 2.30 (18) |
O2—N5—C12—C13 | −34.28 (17) | C2—C11—C16—C15 | 178.86 (11) |
C3A—C1—C2—C11 | −179.60 (11) | C12—C11—C16—C15 | −2.57 (18) |
C2—C1—C3A—N4A | 17.38 (18) | N5—C12—C13—C14 | −178.28 (12) |
C2—C1—C3A—C3 | −163.05 (11) | C11—C12—C13—C14 | −0.2 (2) |
C1—C2—C11—C12 | 159.64 (12) | C12—C13—C14—C15 | −1.7 (2) |
C1—C2—C11—C16 | −21.91 (18) | C13—C14—C15—C16 | 1.4 (2) |
N2—C3—C3A—N4A | −179.70 (12) | C14—C15—C16—C11 | 0.8 (2) |
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1/2, y+1/2, −z+3/2; (iii) −x+1, −y+1, −z+1; (iv) x+1/2, −y+3/2, z+1/2; (v) x−1/2, −y+3/2, z−1/2; (vi) −x+1/2, y−1/2, −z+3/2; (vii) x−1/2, −y+1/2, z−1/2; (viii) x+1/2, −y+1/2, z+1/2; (ix) −x+1, −y+1, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O1 | 0.95 | 2.30 | 2.7633 (15) | 109 |
C5A—H5···O2viii | 0.95 | 2.56 | 3.2875 (16) | 134 |
C8—H8···F1 | 0.95 | 2.43 | 3.1362 (15) | 131 |
C8—H8···F2 | 0.95 | 2.47 | 3.2139 (15) | 135 |
C14—H14···O1vii | 0.95 | 2.59 | 3.4551 (17) | 151 |
C16—H16···F3v | 0.95 | 2.55 | 3.2850 (16) | 135 |
Symmetry codes: (v) x−1/2, −y+3/2, z−1/2; (vii) x−1/2, −y+1/2, z−1/2; (viii) x+1/2, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C18H10F3N5O2 |
Mr | 385.31 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 200 |
a, b, c (Å) | 8.0065 (2), 16.9010 (4), 12.0204 (3) |
β (°) | 92.633 (2) |
V (Å3) | 1624.86 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.13 |
Crystal size (mm) | 0.37 × 0.35 × 0.22 |
Data collection | |
Diffractometer | Oxford Diffraction Gemini diffractometer |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2007) |
Tmin, Tmax | 0.899, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15678, 5345, 3157 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.757 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.125, 0.98 |
No. of reflections | 5345 |
No. of parameters | 253 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.35, −0.28 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O1 | 0.95 | 2.30 | 2.7633 (15) | 109 |
C5A—H5···O2i | 0.95 | 2.56 | 3.2875 (16) | 134 |
C8—H8···F1 | 0.95 | 2.43 | 3.1362 (15) | 131 |
C8—H8···F2 | 0.95 | 2.47 | 3.2139 (15) | 135 |
C14—H14···O1ii | 0.95 | 2.59 | 3.4551 (17) | 151 |
C16—H16···F3iii | 0.95 | 2.55 | 3.2850 (16) | 135 |
Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) x−1/2, −y+3/2, z−1/2. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
In addition to purines and pteridines, many other fused heterocyclic ring systems are known. Of these the most important is that containing ring junction nitrogen, in which the nitrogen is common to two rings. The vast majority of these systems do not occur naturally, they have been the subject of many studies from the theoretical viewpoint and for the preparation of biologically active analogues. Earlier studies revealed that most of the compounds derived from 1,2,4-triazoles have been shown to display a wide spectrum of biological activities. Moreover, a few fused triazoles of different heterocycles have been found to be significant anticonvulsant and tranquillizing agents. Also, 1,2,4-triazolo quinoxalines have been reported as antidepressant, cardiotonics and antifatigue agents (Ali et al., 2004; Bicking, 1959; Chimirri et al., 2002; Dawood et al., 2006; Ilkay et al., 2004; Potts, 1961; Trivedi, 1988; Xie et al., 2005).
In the title molecule, C18H10F3N5O2, Fig.1, the [1,2,4]triazolo[4,3-a]quinoxaline unit is nearly planar. The central pyrazine ring makes a dihedral angle of 1.67 (6)° and 2.44 (5)° with that of the 1,2,4-triazole and the fused benzene ring respectively. The nitro phenyl ring makes a dihedral angle of 2.82 (6)°, 3.15 (6)°, and 3.63 (6)° with that of triazole, pyrazine and benzene rings respectively. The nitro group is slightly twisted away from the plane of the attached phenyl ring. C—H···O and C—H···F hydrogen bonds are found in the crystal structure; see Fig. 2., and the hydrogen bond table.