organic compounds
In the title compound, C15H13N3OS, the amide H atom interacts with the amide O atom of an adjacent molecule [NO = 3.027 (4) Å] to form a zigzag chain that runs along the c axis of the monoclinic unit cell.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806037007/xu2124sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806037007/xu2124Isup2.hkl |
CCDC reference: 625044
Computing details top
Data collection: APEXII (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97.
2-Methyl-1H-indole-3-carbaldehyde 2-thienoylhydrazone top
Crystal data top
C15H13N3OS | F(000) = 592 |
Mr = 283.34 | Dx = 1.381 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1415 reflections |
a = 11.688 (2) Å | θ = 2.5–20.8° |
b = 11.546 (2) Å | µ = 0.24 mm−1 |
c = 10.133 (2) Å | T = 295 K |
β = 94.694 (2)° | Block, yellow |
V = 1362.8 (4) Å3 | 0.24 × 0.23 × 0.20 mm |
Z = 4 |
Data collection top
Bruker APEX-II area-detector diffractometer | 1420 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.078 |
Graphite monochromator | θmax = 26.4°, θmin = 1.8° |
φ and ω scans | h = −14→14 |
11514 measured reflections | k = −14→14 |
2793 independent reflections | l = −12→12 |
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)] = 0.075 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.209 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0979P)2 + 0.3022P] where P = (Fo2 + 2Fc2)/3 |
2793 reflections | (Δ/σ)max = 0.001 |
170 parameters | Δρmax = 0.37 e Å−3 |
0 restraints | Δρmin = −0.31 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
S1 | 0.45706 (10) | 0.92616 (10) | 0.73323 (11) | 0.0697 (4) | |
O1 | 0.6319 (2) | 0.7454 (2) | 0.7868 (3) | 0.0626 (8) | |
N1 | 0.6354 (3) | 0.6811 (3) | 0.5739 (3) | 0.0620 (9) | |
H1N | 0.6078 | 0.6867 | 0.4929 | 0.074* | |
N2 | 0.7227 (3) | 0.6032 (3) | 0.6084 (3) | 0.0598 (9) | |
N3 | 0.9457 (3) | 0.2966 (3) | 0.4867 (4) | 0.0646 (10) | |
H3N | 0.9738 | 0.2388 | 0.4466 | 0.078* | |
C1 | 0.3534 (4) | 0.9786 (4) | 0.6195 (4) | 0.0727 (13) | |
H1 | 0.3041 | 1.0391 | 0.6362 | 0.087* | |
C2 | 0.3516 (4) | 0.9229 (4) | 0.5044 (5) | 0.0769 (14) | |
H2 | 0.3005 | 0.9403 | 0.4319 | 0.092* | |
C3 | 0.4352 (4) | 0.8345 (4) | 0.5035 (4) | 0.0705 (13) | |
H3 | 0.4451 | 0.7875 | 0.4308 | 0.085* | |
C4 | 0.4998 (3) | 0.8261 (3) | 0.6221 (4) | 0.0575 (11) | |
C5 | 0.5937 (3) | 0.7485 (4) | 0.6681 (4) | 0.0546 (10) | |
C6 | 0.7387 (3) | 0.5277 (4) | 0.5156 (4) | 0.0598 (11) | |
H6 | 0.6909 | 0.5286 | 0.4375 | 0.072* | |
C7 | 0.8302 (3) | 0.4424 (3) | 0.5327 (4) | 0.0540 (10) | |
C8 | 0.8477 (3) | 0.3562 (4) | 0.4427 (4) | 0.0591 (11) | |
C9 | 0.7834 (4) | 0.3214 (4) | 0.3167 (4) | 0.0749 (13) | |
H9A | 0.7693 | 0.2395 | 0.3176 | 0.112* | |
H9B | 0.8276 | 0.3403 | 0.2439 | 0.112* | |
H9C | 0.7115 | 0.3620 | 0.3071 | 0.112* | |
C10 | 0.9917 (2) | 0.3428 (2) | 0.6028 (2) | 0.0592 (11) | |
C11 | 1.0898 (2) | 0.3142 (2) | 0.6830 (3) | 0.0719 (13) | |
H11 | 1.1366 | 0.2539 | 0.6591 | 0.086* | |
C12 | 1.1179 (2) | 0.3758 (3) | 0.7991 (3) | 0.0757 (14) | |
H12 | 1.1835 | 0.3566 | 0.8528 | 0.091* | |
C13 | 1.0479 (3) | 0.4659 (3) | 0.8348 (2) | 0.0701 (12) | |
H13 | 1.0668 | 0.5071 | 0.9124 | 0.084* | |
C14 | 0.9499 (2) | 0.4946 (2) | 0.7545 (3) | 0.0629 (12) | |
H14 | 0.9031 | 0.5549 | 0.7785 | 0.076* | |
C15 | 0.92173 (18) | 0.4330 (2) | 0.6385 (3) | 0.0533 (10) |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0737 (8) | 0.0623 (8) | 0.0727 (8) | 0.0066 (6) | 0.0034 (6) | −0.0106 (6) |
O1 | 0.0598 (17) | 0.0609 (18) | 0.0678 (19) | 0.0039 (14) | 0.0091 (14) | −0.0019 (15) |
N1 | 0.059 (2) | 0.066 (2) | 0.061 (2) | 0.0119 (19) | 0.0065 (17) | 0.0032 (18) |
N2 | 0.053 (2) | 0.051 (2) | 0.075 (2) | 0.0096 (17) | 0.0049 (17) | 0.0099 (18) |
N3 | 0.070 (2) | 0.043 (2) | 0.083 (3) | 0.0069 (18) | 0.021 (2) | −0.0063 (18) |
C1 | 0.069 (3) | 0.067 (3) | 0.081 (3) | 0.013 (2) | 0.002 (2) | −0.004 (3) |
C2 | 0.071 (3) | 0.086 (4) | 0.072 (3) | 0.020 (3) | −0.006 (2) | 0.001 (3) |
C3 | 0.071 (3) | 0.078 (3) | 0.063 (3) | 0.009 (3) | 0.007 (2) | −0.010 (2) |
C4 | 0.049 (2) | 0.054 (3) | 0.070 (3) | 0.002 (2) | 0.008 (2) | 0.004 (2) |
C5 | 0.057 (3) | 0.054 (3) | 0.055 (3) | −0.012 (2) | 0.015 (2) | −0.009 (2) |
C6 | 0.060 (3) | 0.049 (3) | 0.073 (3) | 0.001 (2) | 0.016 (2) | 0.004 (2) |
C7 | 0.056 (2) | 0.037 (2) | 0.072 (3) | 0.0025 (19) | 0.020 (2) | 0.005 (2) |
C8 | 0.060 (3) | 0.047 (2) | 0.072 (3) | −0.002 (2) | 0.019 (2) | 0.006 (2) |
C9 | 0.082 (3) | 0.066 (3) | 0.078 (3) | −0.007 (3) | 0.014 (3) | −0.005 (2) |
C10 | 0.052 (2) | 0.042 (2) | 0.086 (3) | 0.003 (2) | 0.019 (2) | 0.011 (2) |
C11 | 0.060 (3) | 0.045 (3) | 0.112 (4) | 0.004 (2) | 0.019 (3) | 0.018 (3) |
C12 | 0.056 (3) | 0.078 (3) | 0.093 (4) | −0.003 (3) | 0.004 (2) | 0.026 (3) |
C13 | 0.056 (3) | 0.070 (3) | 0.085 (3) | −0.006 (2) | 0.007 (2) | 0.005 (3) |
C14 | 0.054 (3) | 0.050 (3) | 0.087 (3) | 0.004 (2) | 0.019 (2) | 0.002 (2) |
C15 | 0.055 (2) | 0.036 (2) | 0.072 (3) | −0.0046 (19) | 0.018 (2) | 0.005 (2) |
Geometric parameters (Å, º) top
S1—C1 | 1.713 (5) | C6—H6 | 0.9300 |
S1—C4 | 1.716 (4) | C7—C8 | 1.376 (5) |
O1—C5 | 1.249 (4) | C7—C15 | 1.455 (5) |
N1—C5 | 1.353 (5) | C8—C9 | 1.483 (6) |
N1—N2 | 1.383 (4) | C9—H9A | 0.9600 |
N1—H1N | 0.8600 | C9—H9B | 0.9600 |
N2—C6 | 1.307 (5) | C9—H9C | 0.9600 |
N3—C10 | 1.362 (4) | C10—C11 | 1.3900 |
N3—C8 | 1.379 (5) | C10—C15 | 1.3900 |
N3—H3N | 0.8600 | C11—C12 | 1.3900 |
C1—C2 | 1.330 (6) | C11—H11 | 0.9300 |
C1—H1 | 0.9300 | C12—C13 | 1.3900 |
C2—C3 | 1.413 (6) | C12—H12 | 0.9300 |
C2—H2 | 0.9300 | C13—C14 | 1.3900 |
C3—C4 | 1.370 (5) | C13—H13 | 0.9300 |
C3—H3 | 0.9300 | C14—C15 | 1.3900 |
C4—C5 | 1.463 (6) | C14—H14 | 0.9300 |
C6—C7 | 1.454 (5) | ||
C1—S1—C4 | 91.4 (2) | C6—C7—C15 | 128.9 (4) |
C5—N1—N2 | 119.8 (3) | C7—C8—N3 | 108.1 (4) |
C5—N1—H1N | 120.1 | C7—C8—C9 | 132.4 (4) |
N2—N1—H1N | 120.1 | N3—C8—C9 | 119.5 (4) |
C6—N2—N1 | 113.4 (3) | C8—C9—H9A | 109.5 |
C10—N3—C8 | 110.0 (3) | C8—C9—H9B | 109.5 |
C10—N3—H3N | 125.0 | H9A—C9—H9B | 109.5 |
C8—N3—H3N | 125.0 | C8—C9—H9C | 109.5 |
C2—C1—S1 | 112.2 (4) | H9A—C9—H9C | 109.5 |
C2—C1—H1 | 123.9 | H9B—C9—H9C | 109.5 |
S1—C1—H1 | 123.9 | N3—C10—C11 | 131.3 (2) |
C1—C2—C3 | 113.2 (4) | N3—C10—C15 | 108.7 (2) |
C1—C2—H2 | 123.4 | C11—C10—C15 | 120.0 |
C3—C2—H2 | 123.4 | C12—C11—C10 | 120.0 |
C4—C3—C2 | 112.2 (4) | C12—C11—H11 | 120.0 |
C4—C3—H3 | 123.9 | C10—C11—H11 | 120.0 |
C2—C3—H3 | 123.9 | C13—C12—C11 | 120.0 |
C3—C4—C5 | 131.9 (4) | C13—C12—H12 | 120.0 |
C3—C4—S1 | 111.0 (3) | C11—C12—H12 | 120.0 |
C5—C4—S1 | 117.0 (3) | C12—C13—C14 | 120.0 |
O1—C5—N1 | 122.8 (4) | C12—C13—H13 | 120.0 |
O1—C5—C4 | 121.6 (4) | C14—C13—H13 | 120.0 |
N1—C5—C4 | 115.6 (4) | C13—C14—C15 | 120.0 |
N2—C6—C7 | 120.9 (4) | C13—C14—H14 | 120.0 |
N2—C6—H6 | 119.6 | C15—C14—H14 | 120.0 |
C7—C6—H6 | 119.6 | C14—C15—C10 | 120.0 |
C8—C7—C6 | 124.0 (4) | C14—C15—C7 | 133.9 (2) |
C8—C7—C15 | 107.1 (3) | C10—C15—C7 | 106.0 (2) |
C5—N1—N2—C6 | 166.6 (3) | C15—C7—C8—C9 | 179.3 (4) |
C4—S1—C1—C2 | 0.2 (4) | C10—N3—C8—C7 | −0.1 (4) |
S1—C1—C2—C3 | −0.1 (5) | C10—N3—C8—C9 | 179.5 (3) |
C1—C2—C3—C4 | −0.1 (6) | C8—N3—C10—C11 | −178.9 (2) |
C2—C3—C4—C5 | 179.2 (4) | C8—N3—C10—C15 | 1.4 (3) |
C2—C3—C4—S1 | 0.2 (5) | N3—C10—C11—C12 | −179.7 (3) |
C1—S1—C4—C3 | −0.2 (3) | C15—C10—C11—C12 | 0.0 |
C1—S1—C4—C5 | −179.4 (3) | C10—C11—C12—C13 | 0.0 |
N2—N1—C5—O1 | 1.3 (5) | C11—C12—C13—C14 | 0.0 |
N2—N1—C5—C4 | −178.7 (3) | C12—C13—C14—C15 | 0.0 |
C3—C4—C5—O1 | −170.6 (4) | C13—C14—C15—C10 | 0.0 |
S1—C4—C5—O1 | 8.3 (5) | C13—C14—C15—C7 | −177.6 (3) |
C3—C4—C5—N1 | 9.4 (6) | N3—C10—C15—C14 | 179.8 (3) |
S1—C4—C5—N1 | −171.7 (3) | C11—C10—C15—C14 | 0.0 |
N1—N2—C6—C7 | 177.4 (3) | N3—C10—C15—C7 | −2.0 (2) |
N2—C6—C7—C8 | 175.9 (4) | C11—C10—C15—C7 | 178.2 (2) |
N2—C6—C7—C15 | −7.3 (6) | C8—C7—C15—C14 | 179.8 (2) |
C6—C7—C8—N3 | 176.1 (3) | C6—C7—C15—C14 | 2.7 (5) |
C15—C7—C8—N3 | −1.2 (4) | C8—C7—C15—C10 | 2.0 (3) |
C6—C7—C8—C9 | −3.4 (7) | C6—C7—C15—C10 | −175.2 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1i | 0.86 | 2.27 | 3.027 (4) | 147 |
Symmetry code: (i) x, −y+3/2, z−1/2. |