Literature DB >> 21589183

Diethyl 2-amino-5-[(E)-(furan-2-yl-methyl-idene)amino]-thio-phene-3,4-di-carboxyl-ate.

Stéphane Dufresne1, W G Skene.   

Abstract

In the crystal structure of the title compound, C(15)H(16)N(2)O(5)S, the azomethine adopts the E configuration. The two heterocyclic rings adopt an anti-periplanar orientation. The mean planes of the thio-phene and furan rings are twisted by 2.51 (4)°. The crystal structure exhibits inter-molecular N-H⋯O hydrogen bonding. π-π stacking is also observed, the centroid-to-centroid distance being 3.770 (4) Å.

Entities:  

Year:  2010        PMID： 21589183      PMCID： PMC3009046          DOI： 10.1107/S1600536810043746

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For general background, see: Dufresne & Skene (2008 ▶). For a related crystal structure, see: Skene et al. (2006 ▶)

Experimental

Crystal data

C15H16N2O5S M = 336.36 Monoclinic, a = 9.3452 (19) Å b = 14.635 (3) Å c = 11.343 (2) Å β = 99.73 (3)° V = 1529.0 (5) Å3 Z = 4 Cu Kα radiation μ = 2.14 mm−1 T = 123 K 0.14 × 0.10 × 0.04 mm

Data collection

Bruker SMART 6000 diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.728, T max = 0.920 6320 measured reflections 3005 independent reflections 2475 reflections with I > 2σ(I) R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.037 wR(F 2) = 0.102 S = 1.03 3005 reflections 210 parameters H-atom parameters constrained Δρmax = 0.29 e Å−3 Δρmin = −0.34 e Å−3 Data collection: SMART (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: UdMX (Marris, 2004 ▶). Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810043746/wn2415sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043746/wn2415Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C15H16N2O5SF(000) = 704
Mr = 336.36Dx = 1.461 Mg m−3
Monoclinic, P21/nMelting point: 425(2) K
Hall symbol: -P 2ynCu Kα radiation, λ = 1.54178 Å
a = 9.3452 (19) ÅCell parameters from 3360 reflections
b = 14.635 (3) Åθ = 5.0–38.8°
c = 11.343 (2) ŵ = 2.14 mm−1
β = 99.73 (3)°T = 123 K
V = 1529.0 (5) Å3Block, yellow
Z = 40.14 × 0.10 × 0.04 mm
Bruker SMART 6000 diffractometer3005 independent reflections
Radiation source: rotating anode2475 reflections with I > 2σ(I)
Montel 200 opticsRint = 0.036
Detector resolution: 5.5 pixels mm-1θmax = 72.3°, θmin = 5.0°
ω scansh = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)k = −17→18
Tmin = 0.728, Tmax = 0.920l = −13→13
6320 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0643P)2] where P = (Fo2 + 2Fc2)/3
3005 reflections(Δ/σ)max = 0.001
210 parametersΔρmax = 0.29 e Å−3
0 restraintsΔρmin = −0.34 e Å−3
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.
xyzUiso*/Ueq
S10.15876 (5)0.01058 (3)0.62132 (4)0.02153 (13)
O30.26457 (13)0.20322 (8)0.97617 (10)0.0216 (3)
O50.53448 (13)0.16250 (8)0.86520 (11)0.0229 (3)
O10.53601 (14)0.14839 (10)0.36188 (11)0.0299 (3)
O40.42258 (13)0.28091 (8)0.76310 (11)0.0261 (3)
O20.11370 (14)0.08821 (9)1.00209 (11)0.0280 (3)
N20.37833 (15)0.11513 (10)0.55344 (12)0.0201 (3)
N10.01952 (16)−0.02136 (10)0.80267 (14)0.0247 (3)
H1A−0.0029−0.01080.87370.030*
H1B−0.0274−0.06370.75630.030*
C130.42543 (18)0.20165 (12)0.79259 (14)0.0180 (3)
C20.21155 (17)0.09610 (11)0.82328 (15)0.0177 (3)
C40.29499 (18)0.09523 (12)0.63985 (15)0.0194 (4)
C100.19189 (18)0.12672 (12)0.94126 (15)0.0192 (4)
C30.30893 (17)0.13360 (12)0.75044 (14)0.0175 (3)
C140.65332 (19)0.22184 (13)0.91629 (17)0.0274 (4)
H14A0.62310.26190.97800.033*
H14B0.68300.26080.85330.033*
C10.12570 (18)0.02730 (12)0.76478 (15)0.0191 (4)
C60.42538 (19)0.08612 (12)0.35493 (16)0.0218 (4)
C50.35120 (19)0.07232 (12)0.45285 (15)0.0225 (4)
H50.27570.02810.44350.027*
C110.2356 (2)0.24369 (13)1.08714 (15)0.0259 (4)
H11A0.25260.19841.15280.031*
H11B0.13350.26461.07760.031*
C80.5077 (2)0.08255 (14)0.18213 (16)0.0284 (4)
H80.52040.06750.10310.034*
C70.4049 (2)0.04441 (13)0.24649 (16)0.0272 (4)
H70.3351−0.00140.21910.033*
C90.5836 (2)0.14410 (15)0.25473 (17)0.0316 (5)
H90.66040.18000.23430.038*
C150.7766 (2)0.16205 (14)0.97085 (18)0.0320 (4)
H15A0.74550.12311.03210.048*
H15B0.85830.20021.00750.048*
H15C0.80680.12370.90870.048*
C120.3367 (2)0.32281 (13)1.11445 (17)0.0351 (5)
H12A0.43720.30071.12840.053*
H12B0.31670.35431.18620.053*
H12C0.32270.36531.04670.053*
U11U22U33U12U13U23
S10.0226 (2)0.0245 (2)0.0170 (2)−0.00387 (17)0.00208 (16)−0.00373 (16)
O30.0288 (7)0.0215 (6)0.0158 (6)−0.0027 (5)0.0072 (5)−0.0041 (5)
O50.0206 (6)0.0213 (6)0.0245 (7)−0.0023 (5)−0.0025 (5)−0.0003 (5)
O10.0275 (7)0.0373 (8)0.0254 (7)−0.0063 (6)0.0062 (6)−0.0053 (6)
O40.0286 (7)0.0206 (7)0.0278 (7)−0.0032 (5)0.0013 (5)0.0036 (5)
O20.0310 (7)0.0308 (7)0.0253 (7)−0.0070 (6)0.0134 (6)−0.0019 (6)
N20.0221 (7)0.0234 (8)0.0148 (7)0.0023 (6)0.0036 (6)0.0009 (6)
N10.0242 (8)0.0269 (8)0.0239 (8)−0.0083 (6)0.0069 (6)−0.0038 (6)
C130.0205 (8)0.0216 (9)0.0131 (8)0.0010 (6)0.0060 (6)−0.0011 (6)
C20.0171 (8)0.0183 (8)0.0175 (8)0.0003 (6)0.0028 (6)0.0004 (6)
C40.0191 (8)0.0222 (9)0.0170 (8)0.0003 (7)0.0032 (7)0.0008 (7)
C100.0178 (8)0.0213 (9)0.0184 (8)0.0015 (6)0.0025 (7)0.0006 (7)
C30.0174 (8)0.0184 (8)0.0168 (8)0.0013 (6)0.0032 (6)0.0017 (6)
C140.0222 (9)0.0273 (10)0.0309 (10)−0.0057 (7)−0.0011 (8)−0.0059 (8)
C10.0181 (8)0.0200 (8)0.0185 (8)0.0023 (6)0.0013 (7)0.0006 (7)
C60.0235 (8)0.0226 (9)0.0188 (8)0.0000 (7)0.0022 (7)0.0008 (7)
C50.0267 (9)0.0222 (9)0.0188 (9)−0.0013 (7)0.0041 (7)0.0005 (7)
C110.0380 (10)0.0256 (9)0.0154 (8)0.0023 (8)0.0080 (8)−0.0038 (7)
C80.0314 (10)0.0375 (11)0.0174 (9)0.0075 (8)0.0076 (8)0.0002 (8)
C70.0365 (10)0.0259 (10)0.0198 (9)−0.0008 (8)0.0061 (8)−0.0038 (7)
C90.0266 (10)0.0429 (12)0.0278 (10)−0.0014 (8)0.0115 (8)0.0052 (9)
C150.0236 (9)0.0391 (11)0.0303 (10)0.0003 (8)−0.0043 (8)−0.0037 (9)
C120.0578 (14)0.0241 (10)0.0235 (10)−0.0043 (10)0.0078 (9)−0.0049 (8)
S1—C11.7242 (18)C14—C151.495 (3)
S1—C41.7633 (18)C14—H14A0.99
O3—C101.334 (2)C14—H14B0.99
O3—C111.4573 (19)C6—C71.357 (2)
O5—C131.3272 (19)C6—C51.420 (2)
O5—C141.451 (2)C5—H50.95
O1—C91.364 (2)C11—C121.494 (3)
O1—C61.370 (2)C11—H11A0.99
O4—C131.206 (2)C11—H11B0.99
O2—C101.224 (2)C8—C91.340 (3)
N2—C51.289 (2)C8—C71.416 (3)
N2—C41.382 (2)C8—H80.95
N1—C11.349 (2)C7—H70.95
N1—H1A0.88C9—H90.95
N1—H1B0.88C15—H15A0.98
C13—C31.493 (2)C15—H15B0.98
C2—C11.385 (2)C15—H15C0.98
C2—C31.437 (2)C12—H12A0.98
C2—C101.452 (2)C12—H12B0.98
C4—C31.360 (2)C12—H12C0.98
C1—S1—C491.65 (8)C7—C6—C5129.21 (18)
C10—O3—C11115.96 (13)O1—C6—C5120.86 (16)
C13—O5—C14116.42 (14)N2—C5—C6125.07 (17)
C9—O1—C6105.92 (15)N2—C5—H5117.5
C5—N2—C4118.38 (15)C6—C5—H5117.5
C1—N1—H1A120O3—C11—C12106.90 (15)
C1—N1—H1B120O3—C11—H11A110.3
H1A—N1—H1B120C12—C11—H11A110.3
O4—C13—O5124.46 (16)O3—C11—H11B110.3
O4—C13—C3124.88 (16)C12—C11—H11B110.3
O5—C13—C3110.65 (14)H11A—C11—H11B108.6
C1—C2—C3111.96 (15)C9—C8—C7106.42 (17)
C1—C2—C10120.84 (15)C9—C8—H8126.8
C3—C2—C10127.08 (15)C7—C8—H8126.8
C3—C4—N2126.11 (16)C6—C7—C8106.60 (17)
C3—C4—S1110.77 (13)C6—C7—H7126.7
N2—C4—S1123.06 (13)C8—C7—H7126.7
O2—C10—O3122.79 (16)C8—C9—O1111.14 (17)
O2—C10—C2123.91 (16)C8—C9—H9124.4
O3—C10—C2113.27 (14)O1—C9—H9124.4
C4—C3—C2113.65 (15)C14—C15—H15A109.5
C4—C3—C13121.43 (15)C14—C15—H15B109.5
C2—C3—C13124.67 (15)H15A—C15—H15B109.5
O5—C14—C15107.41 (15)C14—C15—H15C109.5
O5—C14—H14A110.2H15A—C15—H15C109.5
C15—C14—H14A110.2H15B—C15—H15C109.5
O5—C14—H14B110.2C11—C12—H12A109.5
C15—C14—H14B110.2C11—C12—H12B109.5
H14A—C14—H14B108.5H12A—C12—H12B109.5
N1—C1—C2128.96 (16)C11—C12—H12C109.5
N1—C1—S1118.97 (13)H12A—C12—H12C109.5
C2—C1—S1111.94 (13)H12B—C12—H12C109.5
C7—C6—O1109.92 (16)
C14—O5—C13—O43.5 (2)O5—C13—C3—C4−101.12 (18)
C14—O5—C13—C3−177.89 (14)O4—C13—C3—C2−108.6 (2)
C5—N2—C4—C3179.86 (17)O5—C13—C3—C272.8 (2)
C5—N2—C4—S12.9 (2)C13—O5—C14—C15−167.31 (15)
C1—S1—C4—C3−1.07 (14)C3—C2—C1—N1−177.66 (17)
C1—S1—C4—N2176.35 (15)C10—C2—C1—N1−1.3 (3)
C11—O3—C10—O2−5.4 (2)C3—C2—C1—S1−1.82 (18)
C11—O3—C10—C2172.78 (14)C10—C2—C1—S1174.49 (12)
C1—C2—C10—O29.1 (3)C4—S1—C1—N1177.96 (14)
C3—C2—C10—O2−175.17 (17)C4—S1—C1—C21.66 (13)
C1—C2—C10—O3−169.01 (15)C9—O1—C6—C70.0 (2)
C3—C2—C10—O36.7 (2)C9—O1—C6—C5179.52 (17)
N2—C4—C3—C2−177.09 (15)C4—N2—C5—C6178.96 (16)
S1—C4—C3—C20.22 (19)C7—C6—C5—N2179.79 (19)
N2—C4—C3—C13−2.6 (3)O1—C6—C5—N20.3 (3)
S1—C4—C3—C13174.76 (12)C10—O3—C11—C12175.14 (15)
C1—C2—C3—C41.0 (2)O1—C6—C7—C8−0.1 (2)
C10—C2—C3—C4−175.00 (16)C5—C6—C7—C8−179.58 (18)
C1—C2—C3—C13−173.30 (15)C9—C8—C7—C60.2 (2)
C10—C2—C3—C1310.7 (3)C7—C8—C9—O1−0.2 (2)
O4—C13—C3—C477.5 (2)C6—O1—C9—C80.1 (2)
D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i0.882.202.889 (2)135
N1—H1B···O4ii0.882.503.059 (3)122
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N1—H1A⋯O2i0.882.202.889 (2)135
N1—H1B⋯O4ii0.882.503.059 (3)122

Symmetry codes: (i) ; (ii) .

  2 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Unsymmetric pyrrole, thiophene, and furan-conjugated comonomers prepared using azomethine connections: potential new monomers for alternating homocoupled products.

Authors:  Stéphane Dufresne; W G Skene
Journal:  J Org Chem       Date:  2008-04-15       Impact factor: 4.354
  2 in total
  4 in total

1.  Diethyl 2-amino-5-[(E)-(1-methyl-1H-pyrrol-2-yl)methylideneamino]thiophene-3,4-dicarboxylate.

Authors:  Stéphane Dufresne; W G Skene
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-11-20

2.  Diethyl 2-{[3-(2-meth-oxy-benz-yl)thio-phen-2-yl]methyl-idene}malonate.

Authors:  S Ranjith; K Sakthi Murugesan; A Subbiah Pandi; V Dhayalan; A K Mohana Krishnan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-06-18

3.  (4-Methyl-phen-yl)[2-(thio-phen-2-ylcarbon-yl)phen-yl]methanone.

Authors:  V Silambarasan; S Sundaramoorthy; R Sivasakthikumaran; A K Mohanakrishnan; D Velmurugan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-08-17

4.  Diethyl 2,5-bis-[(1E)-(1H-pyrrol-2-yl-methyl-idene)amino]-thio-phene-3,4-dicarboxyl-ate.

Authors:  Stéphane Dufresne; W G Skene
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-08-11
  4 in total

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