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In the mol­ecule of the highly conjugated title compound, C20H18N2O4S3, the thio­phene rings are in an anti­parallel arrangement and both azomethine bonds adopt the thermodynamically stable E isomeric form. The mean planes of the terminal thio­phene rings are twisted by 9.04 (4) and 25.07 (6)° from the mean plane of the azomethine groups and the central thio­phene ring.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806046915/lh2231sup1.cif
Contains datablocks III, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806046915/lh2231IIIsup2.hkl
Contains datablock III

CCDC reference: 620837

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.043
  • wR factor = 0.114
  • Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found




Alert level C GOODF01_ALERT_2_C The least squares goodness of fit parameter lies outside the range 0.80 <> 2.00 Goodness of fit given = 0.728 PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 42 Perc. PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.88 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.30 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C13 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C15 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C16 - C17 ... 1.43 Ang. PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C19 - C20 ... 1.41 Ang.
Alert level G ABSTM02_ALERT_3_G The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.160 0.650 Tmin(prime) and Tmax expected: 0.192 0.624 RR(prime) = 0.802 Please check that your absorption correction is appropriate. PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 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

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: local program; 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: UdMX (Marris, 2004).

Diethyl 2,5-Bis[(E)-thiophen-2-ylmethyleneamino]thiophene-3,4-dicarboxylate top
Crystal data top
C20H18N2O4S3F(000) = 1856
Mr = 446.54Dx = 1.364 Mg m3
Orthorhombic, PbcnCu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2n 2abCell parameters from 25 reflections
a = 17.039 (5) Åθ = 15.0–20.0°
b = 18.642 (8) ŵ = 3.36 mm1
c = 13.690 (4) ÅT = 293 K
V = 4349 (3) Å3Block, red
Z = 80.44 × 0.35 × 0.14 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
1716 reflections with I > 2σ(I)
Radiation source: X-ray sealed tubeRint = 0.091
Graphite monochromatorθmax = 70.0°, θmin = 3.5°
ω scansh = 2020
Absorption correction: gaussian
Gaussian from crystal shape
k = 2222
Tmin = 0.160, Tmax = 0.650l = 1616
32236 measured reflections4 standard reflections every 60 min
4130 independent reflections intensity decay: 0.1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.114 w = 1/[σ2(Fo2) + (0.0464P)2]
S = 0.73(Δ/σ)max = 0.001
4130 reflectionsΔρmax = 0.22 e Å3
265 parametersΔρmin = 0.24 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00082 (4)
Special details top

Experimental. X-ray crystallographic data for I were collected from a single-crystal sample, which was mounted on a glass fiber. Data were collected using an Enraf–Nonius CAD4 diffractometer equipped with FR590 generator, a Kappa goniometer, a standard scintillation counter and a locally modified low temperature device. The initial unit-cell parameters were determined by a least-squares fit of the angular setting of 25 strong reflections. The intensity of some selected strong reflections was monitored during the course of the data collection. Data were corrected for absorption, Lorentz and polarization effects

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.03111 (5)0.11395 (4)0.61847 (7)0.0674 (3)
S20.00949 (6)0.41302 (5)0.60391 (9)0.0949 (4)
S30.01209 (6)0.19013 (5)0.61949 (8)0.0931 (4)
O10.19644 (14)0.23862 (15)0.7010 (2)0.1199 (12)
O20.24756 (13)0.15498 (12)0.60495 (19)0.0898 (8)
O30.21389 (14)0.01777 (14)0.7283 (2)0.0987 (9)
O40.19320 (14)0.02071 (14)0.5763 (2)0.0961 (9)
N10.03035 (15)0.25076 (14)0.6266 (2)0.0664 (7)
N20.01697 (16)0.02824 (13)0.62567 (19)0.0662 (7)
C10.04322 (17)0.17684 (16)0.6311 (2)0.0618 (8)
C20.11562 (18)0.14548 (17)0.6390 (2)0.0618 (9)
C30.11123 (18)0.06926 (17)0.6355 (2)0.0623 (9)
C40.03605 (18)0.04369 (16)0.6258 (2)0.0626 (8)
C50.0385 (2)0.27501 (17)0.6431 (2)0.0672 (9)
H50.07830.24260.65800.081*
C60.05722 (18)0.35027 (16)0.6395 (3)0.0669 (9)
C70.1273 (2)0.38096 (18)0.6650 (3)0.0813 (11)
H70.17080.35530.68650.098*
C80.1256 (2)0.4560 (2)0.6547 (3)0.0979 (13)
H80.16810.48560.66860.117*
C90.0559 (2)0.48015 (19)0.6225 (3)0.1013 (14)
H90.04480.52830.61160.122*
C100.0543 (2)0.04751 (17)0.6269 (2)0.0725 (10)
H100.09280.01220.62840.087*
C110.0785 (2)0.12178 (17)0.6261 (3)0.0725 (10)
C120.1547 (2)0.1460 (2)0.6302 (3)0.0968 (13)
H120.19860.11660.63470.116*
C130.1572 (3)0.2209 (2)0.6266 (4)0.1198 (17)
H130.20360.24710.62840.144*
C140.0854 (3)0.2513 (2)0.6202 (3)0.1052 (14)
H140.07720.30060.61670.126*
C150.1890 (2)0.18586 (19)0.6522 (3)0.0752 (11)
C160.3258 (2)0.1833 (2)0.6175 (3)0.1137 (16)
H16A0.34250.20680.55780.136*
H16B0.32580.21870.66940.136*
C170.3795 (2)0.1267 (2)0.6412 (4)0.162 (2)
H17A0.36730.10810.70480.243*
H17B0.43210.14500.64100.243*
H17C0.37490.08910.59370.243*
C180.1788 (2)0.01971 (19)0.6534 (3)0.0719 (10)
C190.2535 (3)0.0759 (2)0.5909 (4)0.141 (2)
H19A0.30400.05350.60270.169*
H19B0.24040.10520.64710.169*
C200.2572 (3)0.1189 (2)0.5062 (4)0.178 (3)
H20A0.20930.14560.49960.267*
H20B0.30060.15150.51140.267*
H20C0.26420.08880.45000.267*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0555 (4)0.0622 (5)0.0845 (6)0.0017 (4)0.0021 (5)0.0020 (5)
S20.0786 (6)0.0730 (6)0.1331 (10)0.0024 (5)0.0198 (7)0.0105 (7)
S30.1059 (8)0.0717 (6)0.1018 (9)0.0006 (6)0.0003 (7)0.0034 (6)
O10.0670 (16)0.103 (2)0.190 (3)0.0108 (15)0.0076 (18)0.072 (2)
O20.0554 (13)0.0844 (17)0.130 (2)0.0027 (13)0.0139 (16)0.0280 (16)
O30.0881 (19)0.0992 (19)0.109 (2)0.0251 (16)0.0260 (17)0.0080 (18)
O40.0826 (17)0.0826 (17)0.123 (2)0.0265 (15)0.0030 (16)0.0278 (17)
N10.0625 (16)0.0599 (15)0.077 (2)0.0068 (14)0.0027 (16)0.0033 (15)
N20.0666 (17)0.0587 (16)0.0732 (19)0.0052 (13)0.0021 (16)0.0037 (15)
C10.0581 (19)0.0589 (19)0.068 (2)0.0037 (16)0.0037 (18)0.0045 (18)
C20.0583 (19)0.0573 (19)0.070 (2)0.0009 (16)0.0007 (18)0.0065 (18)
C30.0592 (19)0.060 (2)0.067 (2)0.0035 (16)0.0022 (18)0.0089 (18)
C40.0603 (19)0.060 (2)0.068 (2)0.0002 (17)0.0007 (18)0.0050 (18)
C50.065 (2)0.063 (2)0.074 (3)0.0012 (17)0.001 (2)0.0023 (18)
C60.0555 (19)0.060 (2)0.085 (3)0.0063 (16)0.0003 (18)0.0042 (19)
C70.068 (2)0.063 (2)0.113 (3)0.0093 (19)0.008 (2)0.009 (2)
C80.096 (3)0.070 (3)0.128 (4)0.027 (2)0.019 (3)0.012 (3)
C90.103 (3)0.059 (2)0.142 (4)0.009 (2)0.024 (3)0.011 (3)
C100.069 (2)0.064 (2)0.084 (3)0.0013 (18)0.002 (2)0.005 (2)
C110.076 (2)0.063 (2)0.080 (3)0.0081 (18)0.005 (2)0.003 (2)
C120.083 (3)0.074 (3)0.134 (4)0.024 (2)0.010 (3)0.020 (3)
C130.109 (4)0.101 (4)0.149 (5)0.037 (3)0.025 (4)0.018 (3)
C140.147 (4)0.069 (3)0.099 (4)0.032 (3)0.011 (3)0.004 (2)
C150.059 (2)0.064 (2)0.102 (3)0.0023 (19)0.006 (2)0.013 (2)
C160.059 (2)0.105 (3)0.177 (5)0.014 (2)0.017 (3)0.026 (3)
C170.076 (3)0.111 (4)0.298 (8)0.007 (3)0.030 (4)0.002 (4)
C180.062 (2)0.061 (2)0.092 (3)0.0026 (18)0.001 (2)0.003 (2)
C190.114 (3)0.126 (4)0.182 (5)0.073 (3)0.021 (4)0.049 (4)
C200.183 (5)0.119 (4)0.232 (8)0.069 (4)0.010 (5)0.059 (4)
Geometric parameters (Å, º) top
S1—C11.734 (3)C7—H70.93
S1—C41.742 (3)C8—C91.344 (5)
S2—C91.695 (4)C8—H80.93
S2—C61.702 (3)C9—H90.93
S3—C141.692 (4)C10—C111.445 (4)
S3—C111.707 (3)C10—H100.93
O1—C151.196 (4)C11—C121.376 (4)
O2—C151.321 (4)C12—C131.397 (5)
O2—C161.445 (4)C12—H120.93
O3—C181.188 (4)C13—C141.351 (5)
O4—C181.320 (4)C13—H130.93
O4—C191.468 (4)C14—H140.93
N1—C51.278 (3)C16—C171.433 (5)
N1—C11.397 (3)C16—H16a0.97
N2—C101.266 (4)C16—H16b0.97
N2—C41.380 (3)C17—H17a0.96
C1—C21.369 (4)C17—H17b0.96
C2—C31.424 (4)C17—H17c0.96
C2—C151.471 (4)C19—C201.411 (5)
C3—C41.373 (4)C19—H19a0.97
C3—C181.496 (4)C19—H19b0.97
C5—C61.439 (4)C20—H20a0.96
C5—H50.93C20—H20b0.96
C6—C71.370 (4)C20—H20c0.96
C7—C81.406 (4)
C1—S1—C491.31 (15)C11—C12—C13110.8 (4)
C9—S2—C691.45 (17)C11—C12—H12124.6
C14—S3—C1190.8 (2)C13—C12—H12124.6
C15—O2—C16118.7 (3)C14—C13—C12113.2 (4)
C18—O4—C19114.9 (3)C14—C13—H13123.4
C5—N1—C1119.1 (3)C12—C13—H13123.4
C10—N2—C4120.1 (3)C13—C14—S3112.7 (3)
C2—C1—N1124.5 (3)C13—C14—H14123.7
C2—C1—S1112.2 (2)S3—C14—H14123.7
N1—C1—S1123.2 (2)O1—C15—O2123.5 (3)
C1—C2—C3112.1 (3)O1—C15—C2125.4 (3)
C1—C2—C15123.9 (3)O2—C15—C2111.1 (3)
C3—C2—C15124.0 (3)C17—C16—O2110.3 (3)
C4—C3—C2113.5 (3)C17—C16—H16A109.6
C4—C3—C18121.3 (3)O2—C16—H16A109.6
C2—C3—C18124.8 (3)C17—C16—H16B109.6
C3—C4—N2123.9 (3)O2—C16—H16B109.6
C3—C4—S1110.9 (2)H16A—C16—H16B108.1
N2—C4—S1125.2 (2)C16—C17—H17A109.5
N1—C5—C6122.8 (3)C16—C17—H17B109.5
N1—C5—H5118.6H17A—C17—H17B109.5
C6—C5—H5118.6C16—C17—H17C109.5
C7—C6—C5126.3 (3)H17A—C17—H17C109.5
C7—C6—S2111.6 (3)H17B—C17—H17C109.5
C5—C6—S2122.1 (3)O3—C18—O4125.4 (4)
C6—C7—C8111.8 (3)O3—C18—C3123.2 (4)
C6—C7—H7124.1O4—C18—C3111.4 (3)
C8—C7—H7124.1C20—C19—O4108.5 (4)
C9—C8—C7112.6 (3)C20—C19—H19A110
C9—C8—H8123.7O4—C19—H19A110
C7—C8—H8123.7C20—C19—H19B110
C8—C9—S2112.5 (3)O4—C19—H19B110
C8—C9—H9123.8H19A—C19—H19B108.4
S2—C9—H9123.8C19—C20—H20A109.5
N2—C10—C11123.1 (3)C19—C20—H20B109.5
N2—C10—H10118.5H20A—C20—H20B109.5
C11—C10—H10118.5C19—C20—H20C109.5
C12—C11—C10125.7 (3)H20A—C20—H20C109.5
C12—C11—S3112.5 (3)H20B—C20—H20C109.5
C10—C11—S3121.8 (3)
C5—N1—C1—C2163.1 (3)C6—C7—C8—C90.1 (6)
C5—N1—C1—S121.5 (5)C7—C8—C9—S20.1 (5)
C4—S1—C1—C20.8 (3)C6—S2—C9—C80.2 (4)
C4—S1—C1—N1176.7 (3)C4—N2—C10—C11179.5 (3)
N1—C1—C2—C3176.2 (3)N2—C10—C11—C12178.0 (4)
S1—C1—C2—C30.4 (4)N2—C10—C11—S32.1 (5)
N1—C1—C2—C155.3 (6)C14—S3—C11—C120.9 (3)
S1—C1—C2—C15178.9 (3)C14—S3—C11—C10179.0 (3)
C1—C2—C3—C40.5 (5)C10—C11—C12—C13179.1 (4)
C15—C2—C3—C4178.0 (3)S3—C11—C12—C130.7 (5)
C1—C2—C3—C18172.8 (3)C11—C12—C13—C140.1 (6)
C15—C2—C3—C185.7 (6)C12—C13—C14—S30.5 (6)
C2—C3—C4—N2176.7 (3)C11—S3—C14—C130.8 (4)
C18—C3—C4—N24.0 (5)C16—O2—C15—O14.1 (6)
C2—C3—C4—S11.1 (4)C16—O2—C15—C2174.0 (3)
C18—C3—C4—S1173.8 (3)C1—C2—C15—O137.9 (6)
C10—N2—C4—C3172.4 (4)C3—C2—C15—O1140.5 (4)
C10—N2—C4—S15.1 (5)C1—C2—C15—O2144.1 (3)
C1—S1—C4—C31.1 (3)C3—C2—C15—O237.6 (5)
C1—S1—C4—N2176.7 (3)C15—O2—C16—C17129.7 (4)
C1—N1—C5—C6179.6 (3)C19—O4—C18—O35.5 (6)
N1—C5—C6—C7173.4 (4)C19—O4—C18—C3174.2 (3)
N1—C5—C6—S25.1 (5)C4—C3—C18—O3111.2 (4)
C9—S2—C6—C70.2 (3)C2—C3—C18—O360.6 (5)
C9—S2—C6—C5178.9 (3)C4—C3—C18—O468.5 (4)
C5—C6—C7—C8178.9 (4)C2—C3—C18—O4119.7 (4)
S2—C6—C7—C80.2 (4)C18—O4—C19—C20174.5 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···S10.932.593.024 (3)109
C10—H10···S10.932.583.038 (4)111
C16—H16B···O10.972.282.689 (5)104
 

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