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The highly conjugated title compound, C15H16N2O4S2, exhibits an extended planar configuration. This unusual behavior is the result of the azomethine that adopts the E configuration concomitant with the anti­parallel orientation of the thio­phene units. The nitro­gen-containing double bond is also ca 0.04 Å shorter than its carbon analogue.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806017351/xu2038sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806017351/xu2038Isup2.hkl
Contains datablock I

CCDC reference: 611240

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.037
  • wR factor = 0.098
  • Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.64 mm PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1B ... ?
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 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 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: UdMX (Marris, 2004); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: UdMX; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and SHELXTL (Bruker, 1997); software used to prepare material for publication: UdMX.

(E)-Diethyl 2-amino-5-(2-thienylmethyleneamino)thiophene-3,4-dicarboxylate top
Crystal data top
C15H16N2O4S2F(000) = 736
Mr = 352.42Dx = 1.446 Mg m3
Monoclinic, P21/nMelting point = 145–147 K
Hall symbol: -P 2ynCu Kα radiation, λ = 1.54178 Å
a = 9.428 (4) ÅCell parameters from 25 reflections
b = 14.907 (6) Åθ = 15.0–30.0°
c = 11.671 (4) ŵ = 3.18 mm1
β = 99.28 (3)°T = 293 K
V = 1618.8 (11) Å3Block, orange
Z = 40.64 × 0.30 × 0.22 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
3071 independent reflections
Radiation source: Sealed Tube2255 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.062
Detector resolution: 0.0 pixels mm-1θmax = 70.0°, θmin = 4.8°
ω scansh = 1111
Absorption correction: gaussian
(SADABS; Sheldrick, 1996)
k = 1818
Tmin = 0.220, Tmax = 0.580l = 1414
32753 measured reflections
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)] = 0.037H-atom parameters constrained
wR(F2) = 0.098 w = 1/[σ2(Fo2) + (0.0539P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.92(Δ/σ)max < 0.001
3071 reflectionsΔρmax = 0.23 e Å3
211 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: 0.0045 (3)
Special details top

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
S10.14461 (6)0.49009 (3)0.12892 (5)0.05936 (17)
S20.53755 (6)0.33765 (4)0.13414 (6)0.0728 (2)
O10.11736 (18)0.41246 (10)0.50069 (14)0.0713 (4)
O20.27441 (14)0.30405 (9)0.47569 (12)0.0560 (4)
O30.40647 (17)0.22122 (9)0.25292 (14)0.0716 (5)
O40.52193 (14)0.33673 (9)0.34915 (13)0.0603 (4)
N10.02146 (19)0.52321 (12)0.31270 (17)0.0692 (5)
H1A0.00480.51360.38200.083*
H1B0.02480.56450.27080.083*
N20.35443 (18)0.38644 (11)0.05243 (15)0.0552 (4)
C10.1203 (2)0.47345 (13)0.26976 (19)0.0538 (5)
C20.2058 (2)0.40403 (12)0.32357 (18)0.0507 (5)
C30.2954 (2)0.36651 (12)0.24694 (18)0.0500 (5)
C40.2758 (2)0.40471 (13)0.13977 (19)0.0534 (5)
C50.3316 (2)0.43201 (13)0.0420 (2)0.0597 (5)
H50.26090.47610.04950.072*
C60.4087 (2)0.41874 (13)0.13614 (19)0.0558 (5)
C70.3979 (3)0.46933 (15)0.2358 (2)0.0645 (6)
H70.33400.51680.25310.077*
C80.4947 (3)0.44109 (15)0.3088 (2)0.0687 (6)
H80.50170.46780.37970.082*
C90.5758 (2)0.37131 (17)0.2645 (2)0.0701 (6)
H90.64530.34450.30140.084*
C100.1940 (2)0.37624 (13)0.44012 (19)0.0548 (5)
C110.2566 (3)0.26728 (14)0.58779 (19)0.0629 (6)
H11A0.15730.25020.58750.075*
H11B0.28350.31140.64850.075*
C120.3527 (3)0.18666 (15)0.6081 (2)0.0784 (7)
H12A0.32870.14520.54500.118*
H12B0.33980.15820.67950.118*
H12C0.45110.20500.61280.118*
C130.4113 (2)0.29888 (13)0.28262 (18)0.0531 (5)
C140.6400 (2)0.27872 (15)0.3981 (2)0.0697 (6)
H14A0.67380.24460.33700.084*
H14B0.60870.23700.45270.084*
C150.7572 (3)0.33697 (17)0.4583 (2)0.0796 (7)
H15A0.79740.37140.40180.119*
H15B0.83070.30030.50140.119*
H15C0.71900.37680.51030.119*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0601 (3)0.0533 (3)0.0634 (4)0.0062 (2)0.0059 (2)0.0050 (2)
S20.0681 (4)0.0729 (4)0.0775 (4)0.0135 (3)0.0126 (3)0.0113 (3)
O10.0807 (10)0.0659 (9)0.0721 (11)0.0163 (8)0.0269 (9)0.0032 (8)
O20.0638 (8)0.0466 (7)0.0592 (9)0.0030 (6)0.0144 (7)0.0040 (6)
O30.0795 (11)0.0449 (8)0.0885 (12)0.0053 (7)0.0072 (9)0.0101 (8)
O40.0524 (8)0.0457 (7)0.0795 (10)0.0036 (6)0.0010 (7)0.0029 (7)
N10.0687 (12)0.0644 (11)0.0767 (13)0.0200 (9)0.0188 (10)0.0057 (10)
N20.0596 (10)0.0489 (9)0.0577 (11)0.0027 (8)0.0107 (8)0.0017 (8)
C10.0526 (11)0.0465 (10)0.0626 (13)0.0009 (8)0.0103 (9)0.0006 (9)
C20.0503 (10)0.0423 (9)0.0598 (12)0.0005 (8)0.0094 (9)0.0012 (9)
C30.0501 (10)0.0402 (9)0.0595 (12)0.0001 (8)0.0079 (9)0.0001 (9)
C40.0550 (11)0.0451 (10)0.0599 (13)0.0012 (8)0.0083 (9)0.0021 (9)
C50.0672 (13)0.0474 (11)0.0645 (14)0.0015 (9)0.0103 (11)0.0008 (10)
C60.0602 (12)0.0465 (10)0.0603 (13)0.0022 (9)0.0087 (10)0.0008 (9)
C70.0781 (15)0.0523 (11)0.0646 (14)0.0005 (11)0.0163 (12)0.0061 (10)
C80.0781 (15)0.0643 (14)0.0652 (15)0.0132 (12)0.0166 (12)0.0040 (12)
C90.0625 (13)0.0772 (15)0.0735 (16)0.0045 (12)0.0195 (12)0.0023 (13)
C100.0534 (11)0.0465 (10)0.0644 (13)0.0014 (8)0.0097 (10)0.0006 (10)
C110.0784 (14)0.0541 (12)0.0566 (13)0.0054 (11)0.0122 (11)0.0023 (10)
C120.1051 (19)0.0544 (13)0.0731 (17)0.0073 (13)0.0066 (14)0.0089 (12)
C130.0575 (11)0.0442 (10)0.0593 (13)0.0013 (8)0.0144 (9)0.0026 (9)
C140.0570 (13)0.0618 (13)0.0884 (18)0.0129 (10)0.0061 (12)0.0127 (12)
C150.0621 (14)0.0846 (17)0.0877 (19)0.0054 (13)0.0015 (12)0.0091 (14)
Geometric parameters (Å, º) top
S1—C11.714 (2)C5—C61.426 (3)
S1—C41.765 (2)C5—H50.93
S2—C91.696 (2)C6—C71.376 (3)
S2—C61.711 (2)C7—C81.409 (3)
O1—C101.216 (2)C7—H70.93
O2—C101.343 (2)C8—C91.344 (3)
O2—C111.453 (2)C8—H80.93
O3—C131.207 (2)C9—H90.93
O4—C131.322 (2)C11—C121.501 (3)
O4—C141.452 (2)C11—H11a0.97
N1—C11.349 (3)C11—H11b0.97
N1—H1a0.86C12—H12a0.96
N1—H1b0.86C12—H12b0.96
N2—C41.381 (3)C12—H12c0.96
N2—C51.283 (3)C14—C151.489 (3)
C1—C21.397 (3)C14—H14a0.97
C2—C31.439 (3)C14—H14b0.97
C2—C101.443 (3)C15—H15a0.96
C3—C41.359 (3)C15—H15b0.96
C3—C131.496 (3)C15—H15c0.96
C1—S1—C491.58 (10)C8—C9—H9123.7
C9—S2—C691.84 (12)S2—C9—H9123.7
C10—O2—C11116.07 (16)O1—C10—O2122.3 (2)
C13—O4—C14117.33 (16)O1—C10—C2124.31 (19)
C1—N1—H1A120O2—C10—C2113.34 (18)
C1—N1—H1B120O2—C11—C12106.87 (18)
H1A—N1—H1B120O2—C11—H11A110.3
C5—N2—C4119.61 (19)C12—C11—H11A110.3
N1—C1—C2128.6 (2)O2—C11—H11B110.3
N1—C1—S1118.95 (16)C12—C11—H11B110.3
C2—C1—S1112.42 (16)H11A—C11—H11B108.6
C1—C2—C3111.26 (19)C11—C12—H12A109.5
C1—C2—C10120.66 (18)C11—C12—H12B109.5
C3—C2—C10128.04 (18)H12A—C12—H12B109.5
C4—C3—C2113.75 (18)C11—C12—H12C109.5
C4—C3—C13121.55 (18)H12A—C12—H12C109.5
C2—C3—C13124.39 (18)H12B—C12—H12C109.5
C3—C4—N2125.96 (18)O3—C13—O4124.57 (19)
C3—C4—S1110.96 (16)O3—C13—C3125.1 (2)
N2—C4—S1122.87 (15)O4—C13—C3110.34 (16)
N2—C5—C6123.5 (2)O4—C14—C15107.56 (18)
N2—C5—H5118.2O4—C14—H14A110.2
C6—C5—H5118.2C15—C14—H14A110.2
C7—C6—C5126.7 (2)O4—C14—H14B110.2
C7—C6—S2110.74 (17)C15—C14—H14B110.2
C5—C6—S2122.46 (16)H14A—C14—H14B108.5
C6—C7—C8112.3 (2)C14—C15—H15A109.5
C6—C7—H7123.8C14—C15—H15B109.5
C8—C7—H7123.8H15A—C15—H15B109.5
C9—C8—C7112.5 (2)C14—C15—H15C109.5
C9—C8—H8123.7H15A—C15—H15C109.5
C7—C8—H8123.7H15B—C15—H15C109.5
C8—C9—S2112.55 (19)
C4—S1—C1—N1178.58 (17)C9—S2—C6—C70.03 (18)
C4—S1—C1—C21.40 (16)C9—S2—C6—C5176.97 (18)
N1—C1—C2—C3178.6 (2)C5—C6—C7—C8176.9 (2)
S1—C1—C2—C31.8 (2)S2—C6—C7—C80.0 (2)
N1—C1—C2—C100.6 (3)C6—C7—C8—C90.1 (3)
S1—C1—C2—C10176.20 (15)C7—C8—C9—S20.1 (3)
C1—C2—C3—C41.3 (2)C6—S2—C9—C80.10 (19)
C10—C2—C3—C4176.50 (19)C11—O2—C10—O14.4 (3)
C1—C2—C3—C13172.40 (18)C11—O2—C10—C2174.14 (16)
C10—C2—C3—C139.8 (3)C1—C2—C10—O13.8 (3)
C2—C3—C4—N2174.96 (17)C3—C2—C10—O1178.6 (2)
C13—C3—C4—N21.1 (3)C1—C2—C10—O2174.73 (17)
C2—C3—C4—S10.2 (2)C3—C2—C10—O22.9 (3)
C13—C3—C4—S1173.65 (14)C10—O2—C11—C12178.54 (17)
C5—N2—C4—C3175.0 (2)C14—O4—C13—O35.8 (3)
C5—N2—C4—S10.9 (3)C14—O4—C13—C3175.80 (17)
C1—S1—C4—C30.65 (16)C4—C3—C13—O377.1 (3)
C1—S1—C4—N2174.26 (17)C2—C3—C13—O3109.7 (3)
C4—N2—C5—C6179.13 (18)C4—C3—C13—O4101.3 (2)
N2—C5—C6—C7174.6 (2)C2—C3—C13—O471.9 (2)
N2—C5—C6—S21.9 (3)C13—O4—C14—C15174.00 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O10.862.202.778 (3)124
N1—H1A···O1i0.862.222.880 (3)134
Symmetry code: (i) x, y+1, z+1.
 

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