Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807023665/at2295sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807023665/at2295Isup2.hkl |
CCDC reference: 651471
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.003 Å
- R factor = 0.044
- wR factor = 0.132
- Data-to-parameter ratio = 16.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Cimerman et al. (1997); Sutherland & Hoy (1968); Tucker et al. (1975)
A mixture of the 1-(thiophen-2-yl)ethanone (0.1 mol), and acetohydrazide (0.1 mol) was stirred in refluxing ethanol (30 ml) for 5 h to afford the title compound (0.087 mol, yield 87%). Single crystals (I) of suitable for X-ray measurements were obtained by recrystallization from ethanol at room temperature.
NH H atom was found from difference Fourier map and refined freely. H atoms bonded to C atoms were fixed geometrically and allowed to ride on their attached atoms, with C—H = 0.93 - 0.96 Å, and with Uiso(H) = 1.2–1.5Ueq(C).
Schiff bases have received considerable attention in the literature. They are attractive from several points of view, such as the possibility of analytical application (Cimerman, et al., 1997). As part of our search for new schiff base compounds we synthesized the title compound (I), and describe its structure here.
The molecular structure of the title compund (I) is shown in Fig. 1. The values of all the geometric parameters in (I) are normal. The structure is stabilized by the N—H···O hydrogen bonds form a dimer structure, generating an intermolecular R22(8) ring, and intramolecular C—H···O hydrogen bonding interactions.
For related literature, see: Cimerman et al. (1997); Sutherland & Hoy (1968); Tucker et al. (1975)
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
Fig. 1. An ORTEP view of the title compound (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme. |
C8H10N2OS | Z = 4 |
Mr = 182.24 | F(000) = 384 |
Monoclinic, P21/n | Dx = 1.344 Mg m−3 |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 5.2903 (11) Å | θ = 2.3–26.4° |
b = 9.788 (2) Å | µ = 0.31 mm−1 |
c = 17.435 (4) Å | T = 294 K |
β = 94.102 (3)° | Block, colourless |
V = 900.5 (3) Å3 | 0.24 × 0.16 × 0.14 mm |
Bruker SMART CCD area detector diffractometer | 1847 independent reflections |
Radiation source: fine-focus sealed tube | 1435 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
φ and ω scans | θmax = 26.4°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −5→6 |
Tmin = 0.929, Tmax = 0.958 | k = −7→12 |
5012 measured reflections | l = −21→17 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.132 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0625P)2 + 0.4879P] where P = (Fo2 + 2Fc2)/3 |
1847 reflections | (Δ/σ)max < 0.001 |
114 parameters | Δρmax = 0.31 e Å−3 |
1 restraint | Δρmin = −0.33 e Å−3 |
C8H10N2OS | V = 900.5 (3) Å3 |
Mr = 182.24 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 5.2903 (11) Å | µ = 0.31 mm−1 |
b = 9.788 (2) Å | T = 294 K |
c = 17.435 (4) Å | 0.24 × 0.16 × 0.14 mm |
β = 94.102 (3)° |
Bruker SMART CCD area detector diffractometer | 1847 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | 1435 reflections with I > 2σ(I) |
Tmin = 0.929, Tmax = 0.958 | Rint = 0.026 |
5012 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 1 restraint |
wR(F2) = 0.132 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.31 e Å−3 |
1847 reflections | Δρmin = −0.33 e Å−3 |
114 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.22200 (12) | 0.44789 (7) | 0.06956 (4) | 0.0566 (3) | |
O1 | 0.8443 (4) | 0.0201 (2) | −0.09105 (9) | 0.0601 (5) | |
N1 | 0.5822 (3) | 0.23827 (19) | 0.03934 (10) | 0.0405 (4) | |
N2 | 0.7406 (3) | 0.1420 (2) | 0.01056 (10) | 0.0433 (5) | |
C1 | 0.0993 (5) | 0.5464 (3) | 0.13844 (17) | 0.0590 (7) | |
H1 | −0.0331 | 0.6078 | 0.1284 | 0.071* | |
C2 | 0.2152 (5) | 0.5258 (3) | 0.20932 (16) | 0.0542 (6) | |
H2 | 0.1716 | 0.5718 | 0.2531 | 0.065* | |
C3 | 0.4117 (4) | 0.4255 (2) | 0.20935 (14) | 0.0445 (5) | |
H3 | 0.5104 | 0.3982 | 0.2529 | 0.053* | |
C4 | 0.4369 (4) | 0.3738 (2) | 0.13575 (12) | 0.0382 (5) | |
C5 | 0.6116 (4) | 0.2692 (2) | 0.11116 (12) | 0.0363 (5) | |
C6 | 0.8019 (4) | 0.2087 (3) | 0.16943 (13) | 0.0464 (6) | |
H6A | 0.8417 | 0.1173 | 0.1545 | 0.070* | |
H6B | 0.7325 | 0.2071 | 0.2188 | 0.070* | |
H6C | 0.9532 | 0.2632 | 0.1723 | 0.070* | |
C7 | 0.7020 (4) | 0.1030 (2) | −0.06398 (12) | 0.0428 (5) | |
C8 | 0.4802 (5) | 0.1646 (3) | −0.11048 (14) | 0.0525 (6) | |
H8A | 0.4804 | 0.1339 | −0.1628 | 0.079* | |
H8B | 0.4932 | 0.2624 | −0.1089 | 0.079* | |
H8C | 0.3256 | 0.1367 | −0.0894 | 0.079* | |
H2A | 0.871 (3) | 0.104 (3) | 0.0379 (14) | 0.058 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0562 (4) | 0.0665 (5) | 0.0460 (4) | 0.0183 (3) | −0.0035 (3) | 0.0045 (3) |
O1 | 0.0651 (11) | 0.0742 (13) | 0.0402 (9) | 0.0259 (10) | −0.0033 (8) | −0.0083 (9) |
N1 | 0.0392 (9) | 0.0452 (11) | 0.0365 (9) | 0.0038 (8) | −0.0006 (7) | −0.0007 (8) |
N2 | 0.0438 (10) | 0.0493 (11) | 0.0357 (10) | 0.0107 (9) | −0.0042 (8) | −0.0010 (8) |
C1 | 0.0520 (14) | 0.0568 (16) | 0.0684 (17) | 0.0152 (12) | 0.0066 (13) | 0.0005 (13) |
C2 | 0.0512 (14) | 0.0573 (16) | 0.0549 (15) | 0.0008 (11) | 0.0096 (11) | −0.0119 (12) |
C3 | 0.0402 (11) | 0.0487 (14) | 0.0443 (12) | −0.0032 (10) | 0.0008 (9) | −0.0083 (10) |
C4 | 0.0344 (10) | 0.0418 (12) | 0.0377 (11) | −0.0032 (9) | −0.0022 (8) | 0.0013 (9) |
C5 | 0.0331 (10) | 0.0401 (12) | 0.0352 (10) | −0.0040 (9) | −0.0010 (8) | 0.0013 (9) |
C6 | 0.0456 (12) | 0.0532 (14) | 0.0394 (11) | 0.0072 (10) | −0.0048 (9) | −0.0012 (10) |
C7 | 0.0437 (11) | 0.0475 (13) | 0.0365 (11) | 0.0027 (10) | −0.0020 (9) | 0.0022 (10) |
C8 | 0.0533 (14) | 0.0624 (16) | 0.0403 (12) | 0.0073 (12) | −0.0079 (10) | −0.0002 (11) |
S1—C1 | 1.704 (3) | C3—C4 | 1.394 (3) |
S1—C4 | 1.721 (2) | C3—H3 | 0.9300 |
O1—C7 | 1.224 (3) | C4—C5 | 1.464 (3) |
N1—C5 | 1.287 (3) | C5—C6 | 1.500 (3) |
N1—N2 | 1.379 (3) | C6—H6A | 0.9600 |
N2—C7 | 1.356 (3) | C6—H6B | 0.9600 |
N2—H2A | 0.889 (10) | C6—H6C | 0.9600 |
C1—C2 | 1.355 (4) | C7—C8 | 1.504 (3) |
C1—H1 | 0.9300 | C8—H8A | 0.9600 |
C2—C3 | 1.430 (3) | C8—H8B | 0.9600 |
C2—H2 | 0.9300 | C8—H8C | 0.9600 |
C1—S1—C4 | 91.85 (12) | N1—C5—C6 | 126.5 (2) |
C5—N1—N2 | 118.70 (18) | C4—C5—C6 | 119.00 (18) |
C7—N2—N1 | 119.20 (18) | C5—C6—H6A | 109.5 |
C7—N2—H2A | 117.1 (18) | C5—C6—H6B | 109.5 |
N1—N2—H2A | 123.7 (18) | H6A—C6—H6B | 109.5 |
C2—C1—S1 | 112.9 (2) | C5—C6—H6C | 109.5 |
C2—C1—H1 | 123.6 | H6A—C6—H6C | 109.5 |
S1—C1—H1 | 123.6 | H6B—C6—H6C | 109.5 |
C1—C2—C3 | 112.6 (2) | O1—C7—N2 | 120.1 (2) |
C1—C2—H2 | 123.7 | O1—C7—C8 | 122.4 (2) |
C3—C2—H2 | 123.7 | N2—C7—C8 | 117.5 (2) |
C4—C3—C2 | 111.5 (2) | C7—C8—H8A | 109.5 |
C4—C3—H3 | 124.3 | C7—C8—H8B | 109.5 |
C2—C3—H3 | 124.3 | H8A—C8—H8B | 109.5 |
C3—C4—C5 | 128.82 (19) | C7—C8—H8C | 109.5 |
C3—C4—S1 | 111.24 (17) | H8A—C8—H8C | 109.5 |
C5—C4—S1 | 119.93 (15) | H8B—C8—H8C | 109.5 |
N1—C5—C4 | 114.48 (18) | ||
C5—N1—N2—C7 | 176.3 (2) | N2—N1—C5—C4 | 179.08 (18) |
C4—S1—C1—C2 | 0.3 (2) | N2—N1—C5—C6 | −1.2 (3) |
S1—C1—C2—C3 | −0.4 (3) | C3—C4—C5—N1 | 177.0 (2) |
C1—C2—C3—C4 | 0.4 (3) | S1—C4—C5—N1 | −1.9 (3) |
C2—C3—C4—C5 | −179.1 (2) | C3—C4—C5—C6 | −2.7 (3) |
C2—C3—C4—S1 | −0.2 (2) | S1—C4—C5—C6 | 178.39 (17) |
C1—S1—C4—C3 | −0.04 (19) | N1—N2—C7—O1 | 178.3 (2) |
C1—S1—C4—C5 | 179.01 (19) | N1—N2—C7—C8 | −2.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1i | 0.89 (2) | 2.10 (2) | 2.978 (3) | 169 (3) |
C6—H6A···O1i | 0.96 | 2.46 | 3.279 (3) | 143 |
Symmetry code: (i) −x+2, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C8H10N2OS |
Mr | 182.24 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 294 |
a, b, c (Å) | 5.2903 (11), 9.788 (2), 17.435 (4) |
β (°) | 94.102 (3) |
V (Å3) | 900.5 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.31 |
Crystal size (mm) | 0.24 × 0.16 × 0.14 |
Data collection | |
Diffractometer | Bruker SMART CCD area detector |
Absorption correction | Multi-scan (SADABS; Bruker, 1997) |
Tmin, Tmax | 0.929, 0.958 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5012, 1847, 1435 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.626 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.132, 1.06 |
No. of reflections | 1847 |
No. of parameters | 114 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.31, −0.33 |
Computer programs: SMART (Bruker, 1997), SMART, SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1i | 0.89 (2) | 2.10 (2) | 2.978 (3) | 169 (3) |
C6—H6A···O1i | 0.96 | 2.46 | 3.279 (3) | 143 |
Symmetry code: (i) −x+2, −y, −z. |
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Schiff bases have received considerable attention in the literature. They are attractive from several points of view, such as the possibility of analytical application (Cimerman, et al., 1997). As part of our search for new schiff base compounds we synthesized the title compound (I), and describe its structure here.
The molecular structure of the title compund (I) is shown in Fig. 1. The values of all the geometric parameters in (I) are normal. The structure is stabilized by the N—H···O hydrogen bonds form a dimer structure, generating an intermolecular R22(8) ring, and intramolecular C—H···O hydrogen bonding interactions.