In the title molecule, C8H7N3O3S, the triazole and thiazine rings are nearly coplanar, with a dihedral angle of 2.27 (9)°. The methyl carboxylate moiety is also planar and makes a dihedral angle of 7.31 (13)° with the thiazine-triazole mean plane.
Supporting information
CCDC reference: 200748
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.004 Å
- R factor = 0.043
- wR factor = 0.125
- Data-to-parameter ratio = 13.5
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
ABSTY_02 Alert C An _exptl_absorpt_correction_type has been given without
a literature citation. This should be contained in the
_exptl_absorpt_process_details field.
Absorption correction given as \y scan
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1999); software used to prepare material for publication: PARST (Nardelli, 1995).
Crystal data top
C8H7N3O3S | Z = 2 |
Mr = 225.23 | F(000) = 232 |
Triclinic, P1 | Dx = 1.587 Mg m−3 |
a = 4.0299 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.2866 (7) Å | Cell parameters from 25 reflections |
c = 11.9615 (9) Å | θ = 9.4–18.4° |
α = 104.870 (6)° | µ = 0.33 mm−1 |
β = 96.745 (6)° | T = 295 K |
γ = 95.831 (6)° | Prism, colorless |
V = 471.42 (6) Å3 | 0.4 × 0.32 × 0.12 mm |
Data collection top
Enraf-Nonius TurboCAD-4 diffractometer | Rint = 0.011 |
non–profiled θ/2θ scans | θmax = 26.3°, θmin = 3.1° |
Absorption correction: ψ scan | h = −5→0 |
Tmin = 0.880, Tmax = 0.961 | k = −12→12 |
2173 measured reflections | l = −14→14 |
1893 independent reflections | 3 standard reflections every 120 min |
1504 reflections with I > 2σ(I) | intensity decay: 2% |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.043 | w = 1/[σ2(Fo2) + (0.0713P)2 + 0.1626P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.125 | (Δ/σ)max < 0.001 |
S = 1.09 | Δρmax = 0.34 e Å−3 |
1891 reflections | Δρmin = −0.31 e Å−3 |
140 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C8 | 0.2340 (10) | 0.9164 (3) | 0.5996 (3) | 0.0781 (10) | |
H8A | 0.112 | 0.9243 | 0.5283 | 0.117* | |
H8B | 0.4689 | 0.9167 | 0.5924 | 0.117* | |
H8C | 0.2075 | 0.9915 | 0.6632 | 0.117* | |
H3 | −0.206 (7) | 0.562 (3) | 0.584 (2) | 0.045 (7)* | |
C1 | 0.1252 (6) | 0.4384 (2) | 0.83787 (19) | 0.0366 (5) | |
C2 | 0.1100 (6) | 0.6283 (2) | 0.72732 (19) | 0.0390 (5) | |
C3 | −0.1236 (6) | 0.5413 (3) | 0.6464 (2) | 0.0427 (6) | |
C4 | −0.2641 (6) | 0.4073 (2) | 0.6507 (2) | 0.0436 (6) | |
C5 | 0.0011 (6) | 0.2438 (2) | 0.8576 (2) | 0.0432 (6) | |
C6 | 0.0099 (8) | 0.1272 (3) | 0.9099 (3) | 0.0591 (7) | |
H6A | 0.1668 | 0.1536 | 0.9812 | 0.089* | |
H6B | 0.0794 | 0.0522 | 0.8559 | 0.089* | |
H6C | −0.2108 | 0.1008 | 0.9261 | 0.089* | |
C7 | 0.2438 (7) | 0.7655 (3) | 0.7171 (2) | 0.0448 (6) | |
N1 | −0.1906 (6) | 0.2374 (2) | 0.75994 (19) | 0.0468 (5) | |
N2 | −0.1111 (5) | 0.36492 (19) | 0.74501 (17) | 0.0395 (5) | |
N3 | 0.2004 (5) | 0.36592 (19) | 0.90980 (17) | 0.0427 (5) | |
O1 | −0.4942 (5) | 0.3354 (2) | 0.58140 (17) | 0.0627 (6) | |
O2 | 0.4580 (6) | 0.8389 (2) | 0.7893 (2) | 0.0752 (7) | |
O3 | 0.1037 (5) | 0.7906 (2) | 0.62205 (18) | 0.0625 (6) | |
S1 | 0.30459 (16) | 0.60316 (6) | 0.85551 (5) | 0.0407 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C8 | 0.104 (3) | 0.066 (2) | 0.082 (2) | 0.0145 (19) | 0.013 (2) | 0.0509 (19) |
C1 | 0.0394 (12) | 0.0322 (11) | 0.0351 (11) | 0.0000 (9) | 0.0012 (9) | 0.0075 (9) |
C2 | 0.0414 (13) | 0.0413 (12) | 0.0347 (11) | 0.0057 (10) | 0.0024 (9) | 0.0124 (9) |
C3 | 0.0438 (13) | 0.0502 (14) | 0.0337 (11) | 0.0063 (11) | −0.0011 (10) | 0.0137 (10) |
C4 | 0.0439 (14) | 0.0459 (13) | 0.0359 (12) | 0.0024 (11) | −0.0001 (10) | 0.0061 (10) |
C5 | 0.0469 (14) | 0.0321 (11) | 0.0491 (14) | 0.0020 (10) | 0.0057 (11) | 0.0106 (10) |
C6 | 0.0713 (19) | 0.0362 (13) | 0.0714 (19) | 0.0035 (12) | 0.0032 (15) | 0.0224 (13) |
C7 | 0.0504 (15) | 0.0423 (13) | 0.0449 (13) | 0.0082 (11) | 0.0031 (11) | 0.0185 (11) |
N1 | 0.0504 (12) | 0.0327 (10) | 0.0523 (12) | −0.0026 (9) | 0.0037 (10) | 0.0079 (9) |
N2 | 0.0414 (11) | 0.0333 (10) | 0.0386 (10) | −0.0023 (8) | −0.0008 (8) | 0.0063 (8) |
N3 | 0.0515 (12) | 0.0343 (10) | 0.0408 (11) | 0.0016 (9) | −0.0008 (9) | 0.0125 (8) |
O1 | 0.0598 (12) | 0.0580 (12) | 0.0553 (11) | −0.0104 (10) | −0.0196 (9) | 0.0081 (9) |
O2 | 0.0961 (17) | 0.0452 (11) | 0.0741 (14) | −0.0178 (11) | −0.0261 (12) | 0.0263 (10) |
O3 | 0.0712 (13) | 0.0638 (13) | 0.0574 (12) | −0.0020 (10) | −0.0058 (10) | 0.0366 (10) |
S1 | 0.0492 (4) | 0.0338 (3) | 0.0351 (3) | −0.0032 (2) | −0.0060 (2) | 0.0112 (2) |
Geometric parameters (Å, º) top
C8—O3 | 1.447 (3) | C4—O1 | 1.208 (3) |
C8—H8A | 0.96 | C4—N2 | 1.409 (3) |
C8—H8B | 0.96 | C5—N1 | 1.305 (3) |
C8—H8C | 0.96 | C5—N3 | 1.374 (3) |
C1—N3 | 1.305 (3) | C5—C6 | 1.489 (3) |
C1—N2 | 1.373 (3) | C6—H6A | 0.96 |
C1—S1 | 1.723 (2) | C6—H6B | 0.96 |
C2—C3 | 1.339 (4) | C6—H6C | 0.96 |
C2—C7 | 1.498 (3) | C7—O2 | 1.191 (3) |
C2—S1 | 1.731 (2) | C7—O3 | 1.307 (3) |
C3—C4 | 1.452 (3) | N1—N2 | 1.380 (3) |
C3—H3 | 0.87 (3) | | |
| | | |
O3—C8—H8A | 109.5 | N1—C5—C6 | 123.0 (2) |
O3—C8—H8B | 109.5 | N3—C5—C6 | 121.4 (2) |
H8A—C8—H8B | 109.5 | C5—C6—H6A | 109.5 |
O3—C8—H8C | 109.5 | C5—C6—H6B | 109.5 |
H8A—C8—H8C | 109.5 | H6A—C6—H6B | 109.5 |
H8B—C8—H8C | 109.5 | C5—C6—H6C | 109.5 |
N3—C1—N2 | 110.9 (2) | H6A—C6—H6C | 109.5 |
N3—C1—S1 | 124.53 (18) | H6B—C6—H6C | 109.5 |
N2—C1—S1 | 124.57 (17) | O2—C7—O3 | 126.1 (2) |
C3—C2—C7 | 123.2 (2) | O2—C7—C2 | 121.4 (2) |
C3—C2—S1 | 127.09 (19) | O3—C7—C2 | 112.5 (2) |
C7—C2—S1 | 109.74 (17) | C5—N1—N2 | 102.76 (19) |
C2—C3—C4 | 126.0 (2) | C1—N2—N1 | 108.02 (19) |
C2—C3—H3 | 120.6 (18) | C1—N2—C4 | 128.5 (2) |
C4—C3—H3 | 113.4 (18) | N1—N2—C4 | 123.5 (2) |
O1—C4—N2 | 120.9 (2) | C1—N3—C5 | 102.8 (2) |
O1—C4—C3 | 124.6 (2) | C7—O3—C8 | 116.8 (2) |
N2—C4—C3 | 114.5 (2) | C1—S1—C2 | 98.98 (11) |
N1—C5—N3 | 115.6 (2) | | |
| | | |
C7—C2—C3—C4 | −180.0 (2) | C5—N1—N2—C4 | −178.5 (2) |
S1—C2—C3—C4 | 0.6 (4) | O1—C4—N2—C1 | −172.3 (2) |
C2—C3—C4—O1 | 173.6 (3) | C3—C4—N2—C1 | 7.2 (4) |
C2—C3—C4—N2 | −5.9 (4) | O1—C4—N2—N1 | 5.4 (4) |
C3—C2—C7—O2 | −178.0 (3) | C3—C4—N2—N1 | −175.1 (2) |
S1—C2—C7—O2 | 1.5 (3) | N2—C1—N3—C5 | 0.1 (3) |
C3—C2—C7—O3 | 1.0 (4) | S1—C1—N3—C5 | −178.67 (18) |
S1—C2—C7—O3 | −179.53 (18) | N1—C5—N3—C1 | −0.4 (3) |
N3—C5—N1—N2 | 0.5 (3) | C6—C5—N3—C1 | 178.9 (2) |
C6—C5—N1—N2 | −178.8 (2) | O2—C7—O3—C8 | 3.5 (5) |
N3—C1—N2—N1 | 0.2 (3) | C2—C7—O3—C8 | −175.5 (2) |
S1—C1—N2—N1 | 178.98 (16) | N3—C1—S1—C2 | 176.5 (2) |
N3—C1—N2—C4 | 178.2 (2) | N2—C1—S1—C2 | −2.1 (2) |
S1—C1—N2—C4 | −3.1 (4) | C3—C2—S1—C1 | 3.2 (3) |
C5—N1—N2—C1 | −0.4 (3) | C7—C2—S1—C1 | −176.26 (17) |