Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807060308/ci2514sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807060308/ci2514Isup2.hkl |
CCDC reference: 673057
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.007 Å
- R factor = 0.044
- wR factor = 0.081
- Data-to-parameter ratio = 11.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 7
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 25.01 From the CIF: _reflns_number_total 1663 Count of symmetry unique reflns 1186 Completeness (_total/calc) 140.22% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 477 Fraction of Friedel pairs measured 0.402 Are heavy atom types Z>Si present yes 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 2 ALERT level G = General alerts; check 0 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 2 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
A absolute ethanol mixture of thiophene-2-carboxaldehyde (4 mmol) and ethyldiamine (2 mmol) was heated under reflux with stirring for 1.5 h and then filtered to obtain a clear pale yellow solution. Single crystals of the title compound suitable for X-ray diffraction analysis were obtained by vapour diffusion of diethyl ether into the yellow solution.
H atoms were positioned geometrically [C—H = 0.93 (aromatic) or 0.97 Å (methylene)] and refined using a riding model, with Uiso(H) = 1.2Ueq(C).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
C12H12N2S2 | F(000) = 260 |
Mr = 248.36 | Dx = 1.331 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 1008 reflections |
a = 6.4822 (8) Å | θ = 3.2–27.4° |
b = 7.4181 (10) Å | µ = 0.40 mm−1 |
c = 13.1433 (15) Å | T = 298 K |
β = 101.425 (2)° | Block, yellow |
V = 619.48 (13) Å3 | 0.36 × 0.13 × 0.08 mm |
Z = 2 |
Siemens SMART CCD area-detector diffractometer | 1663 independent reflections |
Radiation source: fine-focus sealed tube | 1136 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.046 |
ϕ and ω scans | θmax = 25.0°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −7→7 |
Tmin = 0.869, Tmax = 0.969 | k = −8→5 |
3150 measured reflections | l = −13→15 |
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)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.081 | w = 1/[σ2(Fo2) + (0.0294P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
1663 reflections | Δρmax = 0.19 e Å−3 |
145 parameters | Δρmin = −0.26 e Å−3 |
1 restraint | Absolute structure: Flack (1983); 481 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.03 (12) |
C12H12N2S2 | V = 619.48 (13) Å3 |
Mr = 248.36 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 6.4822 (8) Å | µ = 0.40 mm−1 |
b = 7.4181 (10) Å | T = 298 K |
c = 13.1433 (15) Å | 0.36 × 0.13 × 0.08 mm |
β = 101.425 (2)° |
Siemens SMART CCD area-detector diffractometer | 1663 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 1136 reflections with I > 2σ(I) |
Tmin = 0.869, Tmax = 0.969 | Rint = 0.046 |
3150 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.081 | Δρmax = 0.19 e Å−3 |
S = 1.03 | Δρmin = −0.26 e Å−3 |
1663 reflections | Absolute structure: Flack (1983); 481 Friedel pairs |
145 parameters | Absolute structure parameter: −0.03 (12) |
1 restraint |
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 | 0.08972 (17) | 0.55346 (16) | 0.29575 (9) | 0.0620 (4) | |
S2 | 0.98557 (19) | 0.38242 (15) | 0.95907 (9) | 0.0589 (4) | |
N1 | 0.3457 (6) | 0.4695 (4) | 0.5119 (3) | 0.0544 (10) | |
N2 | 0.7400 (6) | 0.5301 (5) | 0.7551 (3) | 0.0562 (10) | |
C1 | 0.1512 (8) | 0.4405 (6) | 0.4996 (3) | 0.0543 (14) | |
H1 | 0.0983 | 0.3942 | 0.5550 | 0.065* | |
C2 | 0.0056 (7) | 0.4765 (5) | 0.4024 (3) | 0.0473 (12) | |
C3 | −0.2071 (7) | 0.4550 (6) | 0.3820 (4) | 0.0607 (14) | |
H3 | −0.2828 | 0.4144 | 0.4307 | 0.073* | |
C4 | −0.3001 (8) | 0.5010 (7) | 0.2791 (4) | 0.0668 (15) | |
H4 | −0.4439 | 0.4944 | 0.2524 | 0.080* | |
C5 | −0.1594 (7) | 0.5547 (8) | 0.2245 (4) | 0.0625 (13) | |
H5 | −0.1935 | 0.5891 | 0.1552 | 0.075* | |
C6 | 0.9347 (7) | 0.5520 (7) | 0.7699 (3) | 0.0514 (12) | |
H6 | 0.9913 | 0.6062 | 0.7177 | 0.062* | |
C7 | 1.0773 (7) | 0.4971 (5) | 0.8644 (3) | 0.0460 (11) | |
C8 | 1.2899 (7) | 0.5175 (7) | 0.8889 (3) | 0.0634 (14) | |
H8 | 1.3693 | 0.5765 | 0.8474 | 0.076* | |
C9 | 1.3748 (8) | 0.4369 (7) | 0.9864 (4) | 0.0738 (17) | |
H9 | 1.5177 | 0.4373 | 1.0156 | 0.089* | |
C10 | 1.2317 (8) | 0.3615 (7) | 1.0316 (4) | 0.0616 (14) | |
H10 | 1.2623 | 0.3037 | 1.0956 | 0.074* | |
C11 | 0.4766 (7) | 0.4224 (6) | 0.6113 (3) | 0.0619 (14) | |
H11A | 0.5646 | 0.3200 | 0.6027 | 0.074* | |
H11B | 0.3880 | 0.3884 | 0.6596 | 0.074* | |
C12 | 0.6137 (7) | 0.5800 (6) | 0.6546 (3) | 0.0627 (14) | |
H12A | 0.7049 | 0.6127 | 0.6073 | 0.075* | |
H12B | 0.5264 | 0.6833 | 0.6625 | 0.075* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0541 (8) | 0.0700 (9) | 0.0616 (8) | −0.0122 (7) | 0.0105 (6) | 0.0102 (7) |
S2 | 0.0584 (9) | 0.0623 (8) | 0.0572 (8) | −0.0005 (7) | 0.0144 (7) | 0.0098 (6) |
N1 | 0.055 (2) | 0.061 (3) | 0.045 (2) | 0.000 (2) | 0.004 (2) | 0.0015 (17) |
N2 | 0.062 (3) | 0.055 (3) | 0.047 (2) | 0.007 (2) | 0.002 (2) | 0.001 (2) |
C1 | 0.073 (4) | 0.048 (3) | 0.043 (3) | −0.005 (3) | 0.015 (3) | −0.005 (2) |
C2 | 0.050 (3) | 0.043 (3) | 0.050 (3) | −0.006 (2) | 0.011 (2) | −0.007 (2) |
C3 | 0.052 (3) | 0.070 (4) | 0.066 (4) | −0.018 (3) | 0.026 (3) | −0.015 (3) |
C4 | 0.048 (3) | 0.070 (4) | 0.080 (4) | −0.006 (3) | 0.006 (3) | −0.009 (3) |
C5 | 0.061 (3) | 0.059 (3) | 0.060 (3) | −0.006 (3) | −0.006 (3) | 0.005 (3) |
C6 | 0.072 (3) | 0.040 (3) | 0.043 (3) | −0.001 (3) | 0.012 (3) | 0.000 (2) |
C7 | 0.055 (3) | 0.041 (3) | 0.043 (3) | 0.000 (2) | 0.014 (2) | −0.001 (2) |
C8 | 0.056 (3) | 0.076 (4) | 0.060 (3) | −0.017 (3) | 0.017 (3) | −0.001 (3) |
C9 | 0.053 (3) | 0.094 (4) | 0.066 (4) | −0.008 (3) | −0.009 (3) | −0.005 (3) |
C10 | 0.060 (3) | 0.065 (4) | 0.054 (3) | −0.001 (3) | −0.001 (3) | 0.009 (3) |
C11 | 0.072 (3) | 0.063 (4) | 0.047 (3) | 0.002 (3) | 0.002 (3) | 0.007 (2) |
C12 | 0.076 (3) | 0.059 (3) | 0.047 (3) | 0.005 (3) | −0.001 (3) | 0.006 (2) |
S1—C5 | 1.699 (4) | C5—H5 | 0.93 |
S1—C2 | 1.700 (4) | C6—C7 | 1.452 (5) |
S2—C10 | 1.696 (5) | C6—H6 | 0.93 |
S2—C7 | 1.708 (4) | C7—C8 | 1.360 (5) |
N1—C1 | 1.257 (5) | C8—C9 | 1.422 (6) |
N1—C11 | 1.453 (5) | C8—H8 | 0.93 |
N2—C6 | 1.249 (5) | C9—C10 | 1.320 (6) |
N2—C12 | 1.457 (5) | C9—H9 | 0.93 |
C1—C2 | 1.455 (6) | C10—H10 | 0.93 |
C1—H1 | 0.93 | C11—C12 | 1.510 (5) |
C2—C3 | 1.361 (6) | C11—H11A | 0.97 |
C3—C4 | 1.409 (6) | C11—H11B | 0.97 |
C3—H3 | 0.93 | C12—H12A | 0.97 |
C4—C5 | 1.328 (6) | C12—H12B | 0.97 |
C4—H4 | 0.93 | ||
C5—S1—C2 | 91.8 (2) | C8—C7—S2 | 111.4 (3) |
C10—S2—C7 | 91.7 (2) | C6—C7—S2 | 120.6 (3) |
C1—N1—C11 | 117.8 (4) | C7—C8—C9 | 111.1 (4) |
C6—N2—C12 | 118.5 (4) | C7—C8—H8 | 124.5 |
N1—C1—C2 | 122.8 (4) | C9—C8—H8 | 124.5 |
N1—C1—H1 | 118.6 | C10—C9—C8 | 113.7 (4) |
C2—C1—H1 | 118.6 | C10—C9—H9 | 123.1 |
C3—C2—C1 | 127.4 (4) | C8—C9—H9 | 123.1 |
C3—C2—S1 | 110.8 (3) | C9—C10—S2 | 112.0 (4) |
C1—C2—S1 | 121.8 (3) | C9—C10—H10 | 124.0 |
C2—C3—C4 | 112.6 (4) | S2—C10—H10 | 124.0 |
C2—C3—H3 | 123.7 | N1—C11—C12 | 110.4 (3) |
C4—C3—H3 | 123.7 | N1—C11—H11A | 109.6 |
C5—C4—C3 | 112.5 (4) | C12—C11—H11A | 109.6 |
C5—C4—H4 | 123.8 | N1—C11—H11B | 109.6 |
C3—C4—H4 | 123.8 | C12—C11—H11B | 109.6 |
C4—C5—S1 | 112.3 (4) | H11A—C11—H11B | 108.1 |
C4—C5—H5 | 123.8 | N2—C12—C11 | 109.2 (4) |
S1—C5—H5 | 123.8 | N2—C12—H12A | 109.8 |
N2—C6—C7 | 123.3 (4) | C11—C12—H12A | 109.8 |
N2—C6—H6 | 118.4 | N2—C12—H12B | 109.8 |
C7—C6—H6 | 118.4 | C11—C12—H12B | 109.8 |
C8—C7—C6 | 127.9 (4) | H12A—C12—H12B | 108.3 |
C11—N1—C1—C2 | −177.9 (4) | N2—C6—C7—S2 | 4.7 (7) |
N1—C1—C2—C3 | −177.9 (4) | C10—S2—C7—C8 | −0.1 (4) |
N1—C1—C2—S1 | 2.4 (6) | C10—S2—C7—C6 | 177.0 (4) |
C5—S1—C2—C3 | −0.4 (4) | C6—C7—C8—C9 | −176.7 (4) |
C5—S1—C2—C1 | 179.2 (4) | S2—C7—C8—C9 | 0.2 (5) |
C1—C2—C3—C4 | −179.4 (4) | C7—C8—C9—C10 | −0.2 (6) |
S1—C2—C3—C4 | 0.2 (5) | C8—C9—C10—S2 | 0.2 (6) |
C2—C3—C4—C5 | 0.2 (6) | C7—S2—C10—C9 | −0.1 (4) |
C3—C4—C5—S1 | −0.5 (6) | C1—N1—C11—C12 | −128.7 (4) |
C2—S1—C5—C4 | 0.6 (5) | C6—N2—C12—C11 | 127.3 (5) |
C12—N2—C6—C7 | −176.2 (4) | N1—C11—C12—N2 | 178.9 (4) |
N2—C6—C7—C8 | −178.7 (5) |
Experimental details
Crystal data | |
Chemical formula | C12H12N2S2 |
Mr | 248.36 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 298 |
a, b, c (Å) | 6.4822 (8), 7.4181 (10), 13.1433 (15) |
β (°) | 101.425 (2) |
V (Å3) | 619.48 (13) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.40 |
Crystal size (mm) | 0.36 × 0.13 × 0.08 |
Data collection | |
Diffractometer | Siemens SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.869, 0.969 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3150, 1663, 1136 |
Rint | 0.046 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.081, 1.03 |
No. of reflections | 1663 |
No. of parameters | 145 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.19, −0.26 |
Absolute structure | Flack (1983); 481 Friedel pairs |
Absolute structure parameter | −0.03 (12) |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.
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Multi-dentate complexes of iron and nickel show high activities of ethylene oligomerization and polymerization (Ittle et al., 2000). We report here the crystal structure of the title compound, a new multidentate Schiff base compound.
The molecular structure of the title compound is shown in Fig.1. The molecule adopts a Z-shaped conformation, with the two thiophene rings lying on either side of the C11—C12 bond. The torsion angles C11—N1—C1—C2 [-177.9 (4)°], N1—C11—C12—N2 [178.9 (4)°] and C12—N2—C6—C7 [-176.2 (4)°] describe the overall conformation of the molecule. The two thiophene rings form a dihedral angle of 11.2 (2)°. The crystal packing is mainly stabilized by van der Waals forces.