Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807023768/lw2014sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807023768/lw2014Isup2.hkl |
CCDC reference: 657709
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.003 Å
- R factor = 0.031
- wR factor = 0.084
- Data-to-parameter ratio = 12.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ? PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.14 Ratio
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 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
1,4-dicarboxyaldehyde (0.1 mol, 0,134 g) was heated in ethanol to 313 K and the mixture stirred for 15 min. 2-aminothiophenol (0.2 mol, 0,250 g) was added dropwise over 10 min. The temperature was maintained at this temperature for 2 h with efficient stirring before cooling to room temperature. The resulting yellow powder was filtered and dried overnight. The solid was recrystallized with methanol to yield 1,4-bis(benzothiazol-2-yl)benzene as yellow crystals. (yield: 0.28 g, 82%; m.p. 436 K).
H10 and H8 atoms where located in a difference map and refined with distances of C10—H10 = 0.91 (2) Å and C8—H8 = 0.95 (2) and withUiso(H) = 1.2Ueq(C). The others H atoms bonded to phenyl carbon atoms were obtained geometrically, the C—H distances fixed (0.93 Å for Csp2 H atoms),and the atoms refined as riding on their respective C atoms, with anisotropic displacement parameter 1.2 times the Ueq value for the attached Csp2 atom.
In this work we communicate the synthesis and the structural characterization of the C20H12N2S2, molecule (I). Organic molecules with pairs of free electrons can be useful as ligand precursors in the synthesis of coordination complexes. The other very interesting aspect for this study are the intermolecular interactions driven by C—H··· π, directional forces, a feature with known influence to the development of supramolecular architectures. Even as weak interactions, is now clear that they play an important role in the tuning and prediction of important supramolecular precursors.
Compound (I) was synthesized considering the above statements, and his structural analysis showed a central phenyl ring environment hardwired with two phenylthiazole terminations, scheme 1. Figure 1 shows an ORTEP plot corresponding to 70% probability ellipsoids. Distance parameters of C—C, C—S and C—N bonds shown in table 1 are in good agreement with literature values (Allen et al., 1987).
The crystal structure is stabilized by a single intramolecular C—H···S hydrogen bond (Jeffrey et al., 1985) producing a five-membered ring. The corresponding geometric parameters are listed in table 2.
The C1/C2/S1/C7/N1 ring derives from the plane of C8/C9/C10/C10ii/C9ii/C8ii [Symmetry code: (ii) = -x, 1 - y, -z)] ring from 18,3(1)°.
For related literature, see: Allen et al. (1987); Jeffrey et al. (1985).
Data collection: COLLECT (Nonius, 1998); cell refinement: PhiChi (Duisenberg et al., 2000); data reduction: DIRAX (Duisenberg, 1992); 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, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C20H12N2S2 | F(000) = 712 |
Mr = 344.44 | Dx = 1.432 Mg m−3 |
Monoclinic, C2/c | Melting point: 436 K |
Hall symbol: -C 2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 22.702 (5) Å | θ = 1–27.5° |
b = 6.4839 (13) Å | µ = 0.34 mm−1 |
c = 11.626 (2) Å | T = 295 K |
β = 110.96 (3)° | Block, yellow |
V = 1598.1 (6) Å3 | 0.4 × 0.04 × 0.04 mm |
Z = 4 |
Nonius KappaCCD diffractometer | 1230 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.046 |
Graphite monochromator | θmax = 25.5°, θmin = 3.3° |
φ scans, and ω scans with κ | h = −26→27 |
8151 measured reflections | k = −7→7 |
1475 independent reflections | l = −12→14 |
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)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.084 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0408P)2 + 1.278P] where P = (Fo2 + 2Fc2)/3 |
1475 reflections | (Δ/σ)max < 0.001 |
117 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
C20H12N2S2 | V = 1598.1 (6) Å3 |
Mr = 344.44 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 22.702 (5) Å | µ = 0.34 mm−1 |
b = 6.4839 (13) Å | T = 295 K |
c = 11.626 (2) Å | 0.4 × 0.04 × 0.04 mm |
β = 110.96 (3)° |
Nonius KappaCCD diffractometer | 1230 reflections with I > 2σ(I) |
8151 measured reflections | Rint = 0.046 |
1475 independent reflections |
R[F2 > 2σ(F2)] = 0.031 | 0 restraints |
wR(F2) = 0.084 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.19 e Å−3 |
1475 reflections | Δρmin = −0.24 e Å−3 |
117 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. Distance BIND 3.1392 (0.0019) C10 - S1 2.7569 (0.0222) S1 - H10 3.4624 (0.0036) C10 - C10_$2 2.8586 (0.0226) H10 - C10_$2 Angle ANG 106.71 (1.61) C10 - H10 - S1 125.40 (1.70) C10 - H10 - C10_$2 Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 17.7363 (0.0131) x + 3.6740 (0.0046) y - 0.4059 (0.0069) z = 1.9060 (0.0018) * -0.0041 (0.0011) C1 * 0.0057 (0.0009) C2 * -0.0050 (0.0007) S1 * 0.0042 (0.0009) C7 * -0.0009 (0.0010) N1 Rms deviation of fitted atoms = 0.0043 19.8212 (0.0150) x + 3.1548 (0.0058) y - 3.9670 (0.0119) z = 1.5774 (0.0029) Angle to previous plane (with approximate e.s.d.) = 18.25 (0.10) * -0.0001 (0.0010) C8 * 0.0001 (0.0010) C9 * -0.0001 (0.0010) C10 * 0.0001 (0.0010) C10_$1 * -0.0001 (0.0010) C9_$1 * 0.0001 (0.0010) C8_$1 Rms deviation of fitted atoms = 0.0001 17.8471 (0.0109) x + 3.6414 (0.0027) y - 0.4678 (0.0063) z = 1.9056 (0.0016) Angle to previous plane (with approximate e.s.d.) = 17.89 (0.09) * 0.0065 (0.0015) C1 * -0.0071 (0.0015) C6 * -0.0082 (0.0015) C5 * 0.0023 (0.0016) C4 * 0.0064 (0.0014) C3 * 0.0082 (0.0015) C2 * -0.0150 (0.0009) S1 * 0.0008 (0.0012) C7 * 0.0061 (0.0012) N1 Rms deviation of fitted atoms = 0.0077 |
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 | ||
C7 | 0.07816 (8) | 0.1561 (3) | 0.12153 (15) | 0.0281 (4) | |
C8 | 0.01168 (9) | 0.3397 (3) | −0.06910 (16) | 0.0325 (4) | |
C9 | 0.03848 (8) | 0.3333 (2) | 0.05965 (14) | 0.0267 (4) | |
C10 | 0.02618 (9) | 0.4955 (3) | 0.12723 (16) | 0.0332 (4) | |
N1 | 0.10344 (7) | 0.0265 (2) | 0.06667 (13) | 0.0312 (3) | |
C1 | 0.13679 (8) | −0.1263 (3) | 0.14851 (15) | 0.0299 (4) | |
C2 | 0.13663 (8) | −0.1094 (3) | 0.26963 (15) | 0.0304 (4) | |
C3 | 0.16811 (9) | −0.2525 (3) | 0.36115 (17) | 0.0390 (4) | |
H3 | 0.1678 | −0.2405 | 0.4407 | 0.047* | |
C4 | 0.19969 (9) | −0.4124 (3) | 0.32934 (19) | 0.0434 (5) | |
H4 | 0.2212 | −0.5090 | 0.3887 | 0.052* | |
C5 | 0.19989 (9) | −0.4317 (3) | 0.20961 (19) | 0.0430 (5) | |
H5 | 0.2213 | −0.5413 | 0.1908 | 0.052* | |
C6 | 0.16897 (9) | −0.2915 (3) | 0.11902 (18) | 0.0383 (4) | |
H6 | 0.1694 | −0.3059 | 0.0397 | 0.046* | |
S1 | 0.09188 (2) | 0.10461 (7) | 0.27816 (4) | 0.03404 (17) | |
H8 | 0.0184 (9) | 0.231 (3) | −0.1181 (18) | 0.042 (5)* | |
H10 | 0.0433 (11) | 0.494 (3) | 0.211 (2) | 0.055 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C7 | 0.0315 (9) | 0.0276 (8) | 0.0257 (8) | −0.0022 (7) | 0.0109 (7) | 0.0015 (7) |
C8 | 0.0410 (10) | 0.0297 (9) | 0.0278 (9) | 0.0033 (7) | 0.0135 (8) | −0.0033 (7) |
C9 | 0.0289 (9) | 0.0258 (8) | 0.0269 (8) | −0.0011 (7) | 0.0119 (7) | 0.0014 (7) |
C10 | 0.0412 (10) | 0.0352 (10) | 0.0216 (9) | 0.0034 (8) | 0.0094 (8) | 0.0008 (7) |
N1 | 0.0364 (8) | 0.0303 (8) | 0.0285 (7) | 0.0025 (6) | 0.0134 (6) | 0.0019 (6) |
C1 | 0.0305 (9) | 0.0291 (9) | 0.0304 (8) | −0.0007 (7) | 0.0113 (7) | 0.0018 (7) |
C2 | 0.0306 (9) | 0.0294 (9) | 0.0319 (9) | −0.0004 (7) | 0.0119 (7) | 0.0013 (7) |
C3 | 0.0415 (11) | 0.0413 (10) | 0.0334 (9) | 0.0049 (8) | 0.0125 (8) | 0.0087 (8) |
C4 | 0.0409 (11) | 0.0386 (10) | 0.0478 (11) | 0.0096 (9) | 0.0123 (9) | 0.0132 (9) |
C5 | 0.0388 (11) | 0.0360 (10) | 0.0542 (12) | 0.0087 (8) | 0.0165 (9) | −0.0002 (9) |
C6 | 0.0417 (11) | 0.0374 (10) | 0.0383 (10) | 0.0044 (8) | 0.0174 (8) | −0.0021 (8) |
S1 | 0.0443 (3) | 0.0340 (3) | 0.0256 (2) | 0.00824 (19) | 0.01467 (19) | 0.00382 (17) |
C7—N1 | 1.305 (2) | C1—C2 | 1.414 (2) |
C7—C9 | 1.478 (2) | C2—C3 | 1.400 (2) |
C7—S1 | 1.7659 (17) | C2—S1 | 1.7435 (17) |
C8—C10i | 1.386 (3) | C3—C4 | 1.384 (3) |
C8—C9 | 1.400 (2) | C3—H3 | 0.9300 |
C8—H8 | 0.95 (2) | C4—C5 | 1.399 (3) |
C9—C10 | 1.399 (2) | C4—H4 | 0.9300 |
C10—C8i | 1.386 (3) | C5—C6 | 1.378 (3) |
C10—S1 | 3.1392 (19) | C5—H5 | 0.9300 |
C10—H10 | 0.91 (2) | C6—H6 | 0.9300 |
N1—C1 | 1.394 (2) | S1—H10 | 2.76 (2) |
C1—C6 | 1.406 (2) | ||
N1—C7—C9 | 124.08 (15) | C6—C1—C2 | 119.22 (16) |
N1—C7—S1 | 115.85 (13) | C3—C2—C1 | 121.56 (16) |
C9—C7—S1 | 120.04 (12) | C3—C2—S1 | 129.33 (14) |
C10i—C8—C9 | 120.04 (16) | C1—C2—S1 | 109.09 (12) |
C10i—C8—H8 | 118.8 (12) | C4—C3—C2 | 117.77 (17) |
C9—C8—H8 | 121.1 (12) | C4—C3—H3 | 121.1 |
C10—C9—C8 | 118.70 (15) | C2—C3—H3 | 121.1 |
C10—C9—C7 | 121.34 (15) | C3—C4—C5 | 121.28 (17) |
C8—C9—C7 | 119.95 (15) | C3—C4—H4 | 119.4 |
C8i—C10—C9 | 121.26 (16) | C5—C4—H4 | 119.4 |
C8i—C10—S1 | 169.30 (13) | C6—C5—C4 | 121.27 (17) |
C9—C10—S1 | 63.69 (9) | C6—C5—H5 | 119.4 |
C8i—C10—C10ii | 93.80 (11) | C4—C5—H5 | 119.4 |
C9—C10—C10ii | 131.24 (10) | C5—C6—C1 | 118.90 (17) |
S1—C10—C10ii | 76.92 (5) | C5—C6—H6 | 120.5 |
C8i—C10—H10 | 118.8 (14) | C1—C6—H6 | 120.5 |
C9—C10—H10 | 119.9 (14) | C2—S1—C7 | 89.04 (8) |
S1—C10—H10 | 57.3 (14) | C2—S1—H10 | 153.5 (5) |
C7—N1—C1 | 110.49 (14) | C7—S1—H10 | 68.1 (5) |
N1—C1—C6 | 125.26 (16) | C2—S1—C10 | 141.34 (7) |
N1—C1—C2 | 115.51 (15) | C7—S1—C10 | 52.97 (6) |
C10i—C8—C9—C10 | 0.0 (3) | C4—C5—C6—C1 | 0.1 (3) |
C10i—C8—C9—C7 | 179.20 (16) | N1—C1—C6—C5 | −179.84 (17) |
N1—C7—C9—C10 | −163.27 (17) | C2—C1—C6—C5 | −0.5 (3) |
S1—C7—C9—C10 | 18.7 (2) | C3—C2—S1—C7 | −179.78 (18) |
N1—C7—C9—C8 | 17.6 (3) | C1—C2—S1—C7 | −0.84 (13) |
S1—C7—C9—C8 | −160.46 (13) | C3—C2—S1—H10 | 150.6 (11) |
C8—C9—C10—C8i | 0.0 (3) | C1—C2—S1—H10 | −30.4 (11) |
C7—C9—C10—C8i | −179.19 (16) | C3—C2—S1—C10 | 170.32 (14) |
C8—C9—C10—S1 | 169.13 (17) | C1—C2—S1—C10 | −10.74 (19) |
C7—C9—C10—S1 | −10.02 (12) | N1—C7—S1—C2 | 0.74 (14) |
C8—C9—C10—C10ii | 129.40 (17) | C9—C7—S1—C2 | 178.94 (14) |
C7—C9—C10—C10ii | −49.8 (3) | N1—C7—S1—H10 | 167.0 (5) |
C9—C7—N1—C1 | −178.50 (15) | C9—C7—S1—H10 | −14.8 (5) |
S1—C7—N1—C1 | −0.38 (18) | N1—C7—S1—C10 | 173.01 (17) |
C7—N1—C1—C6 | 179.07 (17) | C9—C7—S1—C10 | −8.79 (11) |
C7—N1—C1—C2 | −0.3 (2) | C8i—C10—S1—C2 | 141.5 (7) |
N1—C1—C2—C3 | 179.88 (16) | C9—C10—S1—C2 | 21.41 (16) |
C6—C1—C2—C3 | 0.5 (3) | C10ii—C10—S1—C2 | 171.84 (10) |
N1—C1—C2—S1 | 0.85 (19) | C8i—C10—S1—C7 | 129.1 (7) |
C6—C1—C2—S1 | −178.58 (14) | C9—C10—S1—C7 | 8.97 (11) |
C1—C2—C3—C4 | 0.0 (3) | C10ii—C10—S1—C7 | 159.40 (10) |
S1—C2—C3—C4 | 178.80 (15) | C8i—C10—S1—H10 | −71.5 (18) |
C2—C3—C4—C5 | −0.4 (3) | C9—C10—S1—H10 | 168.5 (17) |
C3—C4—C5—C6 | 0.4 (3) | C10ii—C10—S1—H10 | −41.1 (17) |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x, y, −z+1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···S1 | 0.91 (2) | 2.75 (2) | 3.139 (2) | 106.7 (14) |
Experimental details
Crystal data | |
Chemical formula | C20H12N2S2 |
Mr | 344.44 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 295 |
a, b, c (Å) | 22.702 (5), 6.4839 (13), 11.626 (2) |
β (°) | 110.96 (3) |
V (Å3) | 1598.1 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.34 |
Crystal size (mm) | 0.4 × 0.04 × 0.04 |
Data collection | |
Diffractometer | Nonius KappaCCD |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8151, 1475, 1230 |
Rint | 0.046 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.031, 0.084, 1.03 |
No. of reflections | 1475 |
No. of parameters | 117 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.19, −0.24 |
Computer programs: COLLECT (Nonius, 1998), PhiChi (Duisenberg et al., 2000), DIRAX (Duisenberg, 1992), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10···S1 | 0.91 (2) | 2.75 (2) | 3.139 (2) | 106.7 (14) |
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In this work we communicate the synthesis and the structural characterization of the C20H12N2S2, molecule (I). Organic molecules with pairs of free electrons can be useful as ligand precursors in the synthesis of coordination complexes. The other very interesting aspect for this study are the intermolecular interactions driven by C—H··· π, directional forces, a feature with known influence to the development of supramolecular architectures. Even as weak interactions, is now clear that they play an important role in the tuning and prediction of important supramolecular precursors.
Compound (I) was synthesized considering the above statements, and his structural analysis showed a central phenyl ring environment hardwired with two phenylthiazole terminations, scheme 1. Figure 1 shows an ORTEP plot corresponding to 70% probability ellipsoids. Distance parameters of C—C, C—S and C—N bonds shown in table 1 are in good agreement with literature values (Allen et al., 1987).
The crystal structure is stabilized by a single intramolecular C—H···S hydrogen bond (Jeffrey et al., 1985) producing a five-membered ring. The corresponding geometric parameters are listed in table 2.
The C1/C2/S1/C7/N1 ring derives from the plane of C8/C9/C10/C10ii/C9ii/C8ii [Symmetry code: (ii) = -x, 1 - y, -z)] ring from 18,3(1)°.