organic compounds
The two independent molecules of the title compound, C12H10N2O3S, are approximately planar and one is stacked over the other. One of the two molecules interacts with its symmetry-related neighbors to form a hydrogen-bonded helical chain that runs along the shortest axis of the orthorhombic unit cell. The second independent molecule does not form such a chain; instead, it is merely linked to the other independent molecule by a hydrogen bond.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680500841X/bt6632sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680500841X/bt6632Isup2.hkl |
CCDC reference: 270249
Computing details top
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
3-Hydroxysalicylaldehyde 2-thienoylhydrazone top
Crystal data top
C12H10N2O3S | F(000) = 1088 |
Mr = 262.28 | Dx = 1.467 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 814 reflections |
a = 7.994 (1) Å | θ = 3.1–22.4° |
b = 11.990 (2) Å | µ = 0.27 mm−1 |
c = 24.787 (4) Å | T = 295 K |
V = 2375.8 (6) Å3 | Block, faint yellow–orange |
Z = 8 | 0.38 × 0.34 × 0.26 mm |
Data collection top
Bruker SMART area-detector diffractometer | 3383 reflections with I > 2σ(I) |
Radiation source: medium-focus sealed tube | Rint = 0.024 |
Graphite monochromator | θmax = 27.2°, θmin = 1.9° |
φ and ω scans | h = −10→7 |
10174 measured reflections | k = −15→7 |
5149 independent reflections | l = −31→31 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.121 | w = 1/[σ2(Fo2) + (0.0638P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
5149 reflections | Δρmax = 0.28 e Å−3 |
329 parameters | Δρmin = −0.40 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 2201 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.05 (9) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
S1 | 0.3597 (1) | 0.60172 (8) | 0.77784 (4) | 0.0690 (3) | |
O1 | 0.8484 (3) | 0.1702 (2) | 1.0558 (1) | 0.0555 (6) | |
O2 | 0.7107 (3) | 0.3025 (2) | 0.9850 (1) | 0.0631 (7) | |
O3 | 0.4717 (3) | 0.4562 (2) | 0.8650 (1) | 0.0619 (6) | |
N1 | 0.6344 (3) | 0.5093 (2) | 0.9555 (1) | 0.0443 (6) | |
N2 | 0.5815 (3) | 0.5882 (2) | 0.9194 (1) | 0.0457 (6) | |
C1 | 0.7805 (4) | 0.3519 (2) | 1.0289 (1) | 0.042 (1) | |
C2 | 0.8544 (4) | 0.2821 (2) | 1.0663 (1) | 0.042 (1) | |
C3 | 0.9260 (4) | 0.3269 (2) | 1.1122 (1) | 0.049 (1) | |
C4 | 0.9252 (4) | 0.4396 (2) | 1.1206 (1) | 0.052 (1) | |
C5 | 0.8542 (4) | 0.5090 (2) | 1.0835 (1) | 0.047 (1) | |
C6 | 0.7811 (3) | 0.4676 (2) | 1.0367 (1) | 0.038 (1) | |
C7 | 0.7140 (4) | 0.5435 (2) | 0.9969 (1) | 0.044 (1) | |
C8 | 0.5075 (4) | 0.5536 (2) | 0.8733 (1) | 0.045 (1) | |
C9 | 0.4724 (4) | 0.6412 (2) | 0.8331 (1) | 0.045 (1) | |
C10 | 0.5161 (4) | 0.7521 (2) | 0.8314 (1) | 0.050 (1) | |
C11 | 0.4522 (5) | 0.8028 (3) | 0.7844 (1) | 0.071 (1) | |
C12 | 0.3670 (5) | 0.7319 (3) | 0.7527 (1) | 0.073 (1) | |
S1' | 0.0760 (2) | 0.72486 (8) | 0.9285 (1) | 0.0790 (3) | |
O1' | 0.6317 (4) | 0.5334 (2) | 1.2548 (1) | 0.0871 (9) | |
O2' | 0.4460 (3) | 0.5700 (2) | 1.1666 (1) | 0.0676 (6) | |
O3' | 0.1817 (3) | 0.6811 (2) | 1.0429 (1) | 0.0597 (6) | |
N1' | 0.3243 (3) | 0.4899 (2) | 1.0776 (1) | 0.0464 (6) | |
N2' | 0.2515 (3) | 0.5009 (2) | 1.0278 (1) | 0.0488 (6) | |
C1' | 0.4981 (4) | 0.4643 (3) | 1.1761 (1) | 0.048 (1) | |
C2' | 0.5925 (4) | 0.4460 (3) | 1.2220 (1) | 0.058 (1) | |
C3' | 0.6503 (5) | 0.3408 (3) | 1.2341 (1) | 0.068 (1) | |
C4' | 0.6127 (5) | 0.2535 (3) | 1.2007 (1) | 0.070 (1) | |
C5' | 0.5212 (4) | 0.2691 (3) | 1.1550 (1) | 0.061 (1) | |
C6' | 0.4625 (4) | 0.3754 (2) | 1.1411 (1) | 0.047 (1) | |
C7' | 0.3763 (4) | 0.3938 (3) | 1.0907 (1) | 0.050 (1) | |
C8' | 0.1843 (3) | 0.5991 (3) | 1.0130 (1) | 0.046 (1) | |
C9' | 0.1127 (3) | 0.6002 (3) | 0.9587 (1) | 0.044 (1) | |
C10' | 0.0664 (4) | 0.5137 (3) | 0.9255 (1) | 0.054 (1) | |
C11' | −0.0026 (4) | 0.5523 (3) | 0.8769 (1) | 0.066 (1) | |
C12' | −0.0015 (5) | 0.6624 (3) | 0.8728 (2) | 0.074 (1) | |
H1o | 0.8930 | 0.1346 | 1.0818 | 0.067* | |
H2o | 0.6785 | 0.3523 | 0.9629 | 0.076* | |
H2n | 0.5949 | 0.6573 | 0.9259 | 0.055* | |
H3 | 0.9750 | 0.2800 | 1.1375 | 0.059* | |
H4 | 0.9733 | 0.4689 | 1.1517 | 0.063* | |
H5 | 0.8546 | 0.5856 | 1.0897 | 0.057* | |
H7 | 0.7294 | 0.6198 | 1.0016 | 0.052* | |
H10 | 0.5790 | 0.7884 | 0.8576 | 0.060* | |
H11 | 0.4675 | 0.8779 | 0.7763 | 0.085* | |
H12 | 0.3174 | 0.7526 | 0.7202 | 0.087* | |
H1o' | 0.6106 | 0.5944 | 1.2387 | 0.105* | |
H2o' | 0.4059 | 0.5743 | 1.1349 | 0.081* | |
H2n' | 0.2488 | 0.4457 | 1.0063 | 0.059* | |
H3' | 0.7145 | 0.3292 | 1.2649 | 0.082* | |
H4' | 0.6503 | 0.1823 | 1.2093 | 0.084* | |
H5' | 0.4974 | 0.2086 | 1.1328 | 0.073* | |
H7' | 0.3585 | 0.3341 | 1.0675 | 0.060* | |
H10' | 0.0792 | 0.4387 | 0.9342 | 0.064* | |
H11' | −0.0447 | 0.5054 | 0.8502 | 0.079* | |
H12' | −0.0392 | 0.7011 | 0.8426 | 0.088* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0816 (6) | 0.0727 (6) | 0.0528 (5) | −0.0001 (5) | −0.0084 (5) | −0.0002 (5) |
O1 | 0.075 (2) | 0.033 (1) | 0.059 (1) | 0.001 (1) | −0.017 (1) | 0.007 (1) |
O2 | 0.090 (2) | 0.041 (1) | 0.058 (1) | 0.011 (1) | −0.028 (1) | −0.006 (1) |
O3 | 0.090 (2) | 0.042 (1) | 0.054 (1) | −0.015 (1) | −0.002 (1) | 0.004 (1) |
N1 | 0.049 (2) | 0.040 (1) | 0.045 (1) | 0.005 (1) | 0.000 (1) | 0.010 (1) |
N2 | 0.058 (2) | 0.033 (1) | 0.046 (1) | 0.002 (1) | −0.001 (1) | 0.006 (1) |
C1 | 0.047 (2) | 0.041 (2) | 0.038 (2) | 0.001 (1) | −0.003 (1) | −0.005 (1) |
C2 | 0.048 (2) | 0.033 (1) | 0.046 (2) | 0.001 (1) | 0.000 (1) | 0.003 (1) |
C3 | 0.051 (2) | 0.049 (2) | 0.046 (2) | 0.002 (2) | −0.005 (2) | 0.011 (1) |
C4 | 0.058 (2) | 0.052 (2) | 0.046 (2) | −0.002 (2) | −0.012 (2) | −0.009 (1) |
C5 | 0.052 (2) | 0.037 (2) | 0.053 (2) | −0.001 (1) | −0.004 (2) | −0.006 (1) |
C6 | 0.042 (2) | 0.036 (2) | 0.037 (2) | −0.002 (1) | 0.000 (1) | −0.003 (1) |
C7 | 0.049 (2) | 0.031 (1) | 0.051 (2) | 0.005 (1) | 0.006 (2) | −0.001 (1) |
C8 | 0.052 (2) | 0.038 (2) | 0.045 (2) | 0.000 (1) | 0.006 (1) | 0.002 (1) |
C9 | 0.048 (2) | 0.045 (2) | 0.041 (2) | 0.006 (1) | 0.000 (1) | 0.003 (1) |
C10 | 0.075 (2) | 0.039 (2) | 0.037 (2) | 0.012 (2) | 0.001 (2) | 0.002 (1) |
C11 | 0.100 (3) | 0.050 (2) | 0.061 (2) | 0.019 (2) | 0.006 (2) | 0.010 (2) |
C12 | 0.097 (3) | 0.078 (3) | 0.043 (2) | 0.033 (2) | −0.004 (2) | 0.006 (2) |
S1' | 0.1027 (7) | 0.0518 (5) | 0.0825 (7) | −0.0038 (5) | −0.0375 (6) | 0.0048 (5) |
O1' | 0.122 (2) | 0.086 (2) | 0.053 (1) | −0.026 (2) | −0.019 (2) | 0.003 (1) |
O2' | 0.105 (2) | 0.044 (1) | 0.054 (1) | 0.006 (1) | −0.016 (1) | −0.003 (1) |
O3' | 0.079 (2) | 0.044 (1) | 0.056 (1) | 0.004 (1) | −0.006 (1) | −0.011 (1) |
N1' | 0.051 (2) | 0.049 (2) | 0.039 (1) | 0.004 (1) | −0.002 (1) | 0.001 (1) |
N2' | 0.056 (2) | 0.047 (1) | 0.044 (1) | 0.008 (1) | −0.008 (1) | −0.009 (1) |
C1' | 0.055 (2) | 0.048 (2) | 0.041 (2) | −0.002 (2) | 0.006 (2) | 0.007 (1) |
C2' | 0.062 (2) | 0.069 (2) | 0.043 (2) | −0.013 (2) | 0.003 (2) | 0.006 (2) |
C3' | 0.064 (2) | 0.089 (3) | 0.052 (2) | 0.007 (2) | 0.001 (2) | 0.028 (2) |
C4' | 0.078 (3) | 0.065 (2) | 0.067 (2) | 0.018 (2) | 0.008 (2) | 0.027 (2) |
C5' | 0.073 (2) | 0.047 (2) | 0.062 (2) | 0.008 (2) | 0.011 (2) | 0.006 (2) |
C6' | 0.052 (2) | 0.046 (2) | 0.043 (2) | −0.002 (1) | 0.008 (1) | 0.006 (1) |
C7' | 0.054 (2) | 0.047 (2) | 0.050 (2) | −0.003 (2) | 0.001 (2) | −0.007 (1) |
C8' | 0.044 (2) | 0.044 (2) | 0.048 (2) | −0.001 (1) | 0.004 (1) | −0.002 (1) |
C9' | 0.041 (2) | 0.046 (2) | 0.045 (2) | 0.001 (1) | −0.001 (1) | −0.001 (1) |
C10' | 0.061 (2) | 0.050 (2) | 0.051 (2) | 0.006 (2) | −0.008 (2) | −0.007 (2) |
C11' | 0.072 (2) | 0.068 (2) | 0.056 (2) | 0.006 (2) | −0.011 (2) | −0.011 (2) |
C12' | 0.084 (3) | 0.080 (3) | 0.058 (2) | 0.000 (2) | −0.026 (2) | 0.008 (2) |
Geometric parameters (Å, º) top
S1—C12 | 1.682 (4) | C2'—C3' | 1.377 (5) |
S1—C9 | 1.706 (3) | C3'—C4' | 1.369 (5) |
O1—C2 | 1.368 (3) | C4'—C5' | 1.361 (4) |
O2—C1 | 1.360 (3) | C5'—C6' | 1.402 (4) |
O3—C8 | 1.220 (3) | C6'—C7' | 1.442 (4) |
N1—C7 | 1.276 (4) | C9'—C10' | 1.374 (4) |
N1—N2 | 1.369 (3) | C9'—C8' | 1.463 (4) |
N2—C8 | 1.352 (4) | C10'—C11' | 1.405 (4) |
C1—C2 | 1.381 (4) | C11'—C12' | 1.324 (5) |
C1—C6 | 1.400 (4) | O1—H1o | 0.85 |
C2—C3 | 1.382 (4) | O2—H2o | 0.85 |
C3—C4 | 1.367 (4) | N2—H2n | 0.85 |
C4—C5 | 1.365 (4) | C3—H3 | 0.93 |
C5—C6 | 1.391 (4) | C4—H4 | 0.93 |
C6—C7 | 1.445 (4) | C5—H5 | 0.93 |
C8—C9 | 1.476 (4) | C7—H7 | 0.93 |
C9—C10 | 1.375 (4) | C10—H10 | 0.93 |
C10—C11 | 1.410 (4) | C11—H11 | 0.93 |
C11—C12 | 1.345 (5) | C12—H12 | 0.93 |
S1'—C12' | 1.687 (4) | O1'—H1o' | 0.85 |
S1'—C9' | 1.697 (3) | O2'—H2o' | 0.85 |
O1'—C2' | 1.364 (4) | N2'—H2n' | 0.85 |
O2'—C1' | 1.353 (4) | C3'—H3' | 0.93 |
O3'—C8' | 1.231 (3) | C4'—H4' | 0.93 |
N1'—C7' | 1.267 (4) | C5'—H5' | 0.93 |
N1'—N2' | 1.371 (3) | C7'—H7' | 0.93 |
N2'—C8' | 1.345 (4) | C10'—H10' | 0.93 |
C1'—C2' | 1.383 (4) | C11'—H11' | 0.93 |
C1'—C6' | 1.404 (4) | C12'—H12' | 0.93 |
C12—S1—C9 | 91.3 (2) | C8'—C9'—S1' | 118.8 (2) |
C7—N1—N2 | 117.2 (2) | O3'—C8'—N2' | 122.8 (3) |
C8—N2—N1 | 118.4 (2) | O3'—C8'—C9' | 122.7 (3) |
O2—C1—C2 | 116.6 (2) | N2'—C8'—C9' | 114.6 (3) |
O2—C1—C6 | 122.9 (2) | C9'—C10'—C11' | 111.7 (3) |
C2—C1—C6 | 120.4 (3) | C12'—C11'—C10' | 113.0 (3) |
O1—C2—C1 | 116.9 (2) | C11'—C12'—S1' | 112.5 (3) |
O1—C2—C3 | 123.5 (2) | C2—O1—H1o | 109.5 |
C1—C2—C3 | 119.6 (3) | C1—O2—H2o | 109.5 |
C4—C3—C2 | 120.6 (3) | C8—N2—H2n | 120.8 |
C5—C4—C3 | 120.1 (3) | N1—N2—H2n | 120.8 |
C4—C5—C6 | 121.3 (3) | C4—C3—H3 | 119.7 |
C5—C6—C1 | 118.1 (3) | C2—C3—H3 | 119.7 |
C5—C6—C7 | 120.0 (2) | C5—C4—H4 | 119.9 |
C1—C6—C7 | 121.9 (3) | C3—C4—H4 | 119.9 |
N1—C7—C6 | 122.1 (2) | C4—C5—H5 | 119.4 |
O3—C8—N2 | 122.6 (3) | C6—C5—H5 | 119.4 |
O3—C8—C9 | 121.5 (3) | N1—C7—H7 | 119.0 |
N2—C8—C9 | 115.9 (2) | C6—C7—H7 | 119.0 |
C10—C9—C8 | 131.3 (3) | C9—C10—H10 | 124.8 |
C10—C9—S1 | 112.2 (2) | C11—C10—H10 | 124.8 |
C8—C9—S1 | 116.5 (2) | C12—C11—H11 | 123.4 |
C9—C10—C11 | 110.5 (3) | C10—C11—H11 | 123.4 |
C12—C11—C10 | 113.2 (3) | C11—C12—H12 | 123.6 |
C11—C12—S1 | 112.8 (3) | S1—C12—H12 | 123.6 |
C12'—S1'—C9' | 91.9 (2) | C2'—O1'—H1o' | 109.5 |
C7'—N1'—N2' | 117.3 (2) | C1'—O2'—H2o' | 109.5 |
C8'—N2'—N1' | 120.0 (2) | C8'—N2'—H2n' | 120.0 |
O2'—C1'—C2' | 117.3 (3) | N1'—N2'—H2n' | 120.0 |
O2'—C1'—C6' | 122.7 (3) | C4'—C3'—H3' | 120.2 |
C2'—C1'—C6' | 119.9 (3) | C2'—C3'—H3' | 120.2 |
O1'—C2'—C3' | 119.8 (3) | C5'—C4'—H4' | 119.5 |
O1'—C2'—C1' | 119.6 (3) | C3'—C4'—H4' | 119.5 |
C3'—C2'—C1' | 120.6 (3) | C4'—C5'—H5' | 119.6 |
C4'—C3'—C2' | 119.6 (3) | C6'—C5'—H5' | 119.6 |
C5'—C4'—C3' | 121.1 (3) | N1'—C7'—H7' | 119.4 |
C4'—C5'—C6' | 120.7 (3) | C6'—C7'—H7' | 119.4 |
C5'—C6'—C1' | 118.0 (3) | C9'—C10'—H10' | 124.1 |
C5'—C6'—C7' | 120.8 (3) | C11'—C10'—H10' | 124.1 |
C1'—C6'—C7' | 121.0 (3) | C12'—C11'—H11' | 123.5 |
N1'—C7'—C6' | 121.2 (3) | C10'—C11'—H11' | 123.5 |
C10'—C9'—C8' | 130.4 (3) | C11'—C12'—H12' | 123.7 |
C10'—C9'—S1' | 110.8 (2) | S1'—C12'—H12' | 123.7 |
C7—N1—N2—C8 | 175.3 (3) | C7'—N1'—N2'—C8' | 175.7 (3) |
O2—C1—C2—O1 | −0.8 (4) | O2'—C1'—C2'—O1' | −1.2 (5) |
C6—C1—C2—O1 | 179.9 (3) | C6'—C1'—C2'—O1' | 177.7 (3) |
O2—C1—C2—C3 | −179.3 (3) | O2'—C1'—C2'—C3' | −179.8 (3) |
C6—C1—C2—C3 | 1.4 (4) | C6'—C1'—C2'—C3' | −0.9 (5) |
O1—C2—C3—C4 | −178.9 (3) | O1'—C2'—C3'—C4' | −179.1 (3) |
C1—C2—C3—C4 | −0.5 (5) | C1'—C2'—C3'—C4' | −0.5 (5) |
C2—C3—C4—C5 | −0.3 (5) | C2'—C3'—C4'—C5' | 1.1 (6) |
C3—C4—C5—C6 | 0.1 (5) | C3'—C4'—C5'—C6' | −0.2 (5) |
C4—C5—C6—C1 | 0.8 (5) | C4'—C5'—C6'—C1' | −1.2 (5) |
C4—C5—C6—C7 | −177.0 (3) | C4'—C5'—C6'—C7' | 175.3 (3) |
O2—C1—C6—C5 | 179.2 (3) | O2'—C1'—C6'—C5' | −179.4 (3) |
C2—C1—C6—C5 | −1.5 (5) | C2'—C1'—C6'—C5' | 1.7 (4) |
O2—C1—C6—C7 | −3.1 (5) | O2'—C1'—C6'—C7' | 4.0 (4) |
C2—C1—C6—C7 | 176.2 (2) | C2'—C1'—C6'—C7' | −174.8 (3) |
N2—N1—C7—C6 | −177.8 (2) | N2'—N1'—C7'—C6' | 176.7 (2) |
C5—C6—C7—N1 | −174.4 (3) | C5'—C6'—C7'—N1' | −179.3 (3) |
C1—C6—C7—N1 | 7.9 (4) | C1'—C6'—C7'—N1' | −2.8 (4) |
N1—N2—C8—O3 | 7.3 (4) | C12'—S1'—C9'—C10' | 0.5 (3) |
N1—N2—C8—C9 | −172.6 (2) | C12'—S1'—C9'—C8' | −179.3 (2) |
O3—C8—C9—C10 | −172.6 (3) | N1'—N2'—C8'—O3' | −1.5 (5) |
N2—C8—C9—C10 | 7.3 (4) | N1'—N2'—C8'—C9' | 179.2 (2) |
O3—C8—C9—S1 | 6.7 (4) | C10'—C9'—C8'—O3' | −161.6 (3) |
N2—C8—C9—S1 | −173.4 (2) | S1'—C9'—C8'—O3' | 18.2 (4) |
C12—S1—C9—C10 | −0.8 (2) | C10'—C9'—C8'—N2' | 17.7 (5) |
C12—S1—C9—C8 | 179.7 (2) | S1'—C9'—C8'—N2' | −162.5 (2) |
C8—C9—C10—C11 | −179.6 (3) | C8'—C9'—C10'—C11' | 178.0 (3) |
S1—C9—C10—C11 | 1.0 (3) | S1'—C9'—C10'—C11' | −1.8 (3) |
C9—C10—C11—C12 | −0.7 (4) | C9'—C10'—C11'—C12' | 2.6 (5) |
C10—C11—C12—S1 | 0.1 (4) | C10'—C11'—C12'—S1' | −2.2 (5) |
C9—S1—C12—C11 | 0.4 (3) | C9'—S1'—C12'—C11' | 1.0 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1o···O3i | 0.85 | 1.82 | 2.668 (3) | 173 |
O2—H2o···N1 | 0.85 | 1.92 | 2.656 (3) | 144 |
N2—H2n···O3′ii | 0.85 | 2.20 | 3.028 (3) | 165 |
O1′—H1o′···O2′ | 0.85 | 2.24 | 2.679 (3) | 112 |
O2′—H2o′···N1′ | 0.85 | 1.86 | 2.595 (3) | 144 |
N2′—H2n′···O1iii | 0.85 | 2.22 | 3.017 (3) | 156 |
Symmetry codes: (i) x+1/2, −y+1/2, −z+2; (ii) x+1/2, −y+3/2, −z+2; (iii) x−1/2, −y+1/2, −z+2. |