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The title compound, C18H19NO5, synthesized via a thia­zole carbene-mediated multicomponent reaction, has a crystal structure stabilized by π–π stacking inter­actions involving the phenyl and furan rings.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806022586/bh2028sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806022586/bh2028Isup2.hkl
Contains datablock I

CCDC reference: 614855

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.048
  • wR factor = 0.144
  • Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.05
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); 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).

(E)-Dimethyl 4-(ethylamino)-5-styrylfuran-2,3-dicarboxylate top
Crystal data top
C18H19NO5Z = 2
Mr = 329.34F(000) = 348
Triclinic, P1Dx = 1.313 Mg m3
Hall symbol: -P 1Melting point = 391–392 K
a = 7.765 (4) ÅMo Kα radiation, λ = 0.71075 Å
b = 9.043 (4) ÅCell parameters from 5627 reflections
c = 13.044 (11) Åθ = 3.1–27.5°
α = 70.17 (3)°µ = 0.10 mm1
β = 82.36 (3)°T = 298 K
γ = 75.52 (3)°Needle, orange
V = 833.1 (9) Å30.57 × 0.18 × 0.16 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
Rint = 0.027
Detector resolution: 10.00 pixels mm-1θmax = 27.5°, θmin = 3.1°
ω scansh = 910
8262 measured reflectionsk = 1111
3772 independent reflectionsl = 1616
2119 reflections with I > 2σ(I)
Refinement top
Refinement on F2H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.0782P)2]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.048(Δ/σ)max < 0.001
wR(F2) = 0.144Δρmax = 0.26 e Å3
S = 0.99Δρmin = 0.27 e Å3
3772 reflectionsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
225 parametersExtinction coefficient: 0.032 (6)
0 restraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.4641 (2)0.0790 (2)0.62418 (14)0.0462 (4)
C20.4491 (2)0.0730 (2)0.68415 (14)0.0478 (4)
C30.5915 (2)0.1377 (2)0.75712 (15)0.0498 (5)
C40.6854 (2)0.0196 (2)0.73558 (15)0.0481 (4)
C50.8351 (2)0.0030 (2)0.78157 (15)0.0498 (5)
H50.88930.09130.83740.06*
C60.9023 (2)0.1275 (2)0.75108 (16)0.0531 (5)
H60.84880.21350.69360.064*
C71.0501 (2)0.1523 (2)0.79683 (15)0.0489 (4)
C81.1458 (2)0.0342 (2)0.88139 (16)0.0598 (5)
H81.1160.06580.91110.072*
C91.2843 (3)0.0638 (3)0.9215 (2)0.0748 (7)
H91.34780.01680.97770.09*
C101.3300 (3)0.2103 (3)0.8799 (2)0.0794 (7)
H101.42360.22940.90770.095*
C111.2372 (3)0.3281 (3)0.7974 (2)0.0773 (7)
H111.26740.4280.76850.093*
C121.0988 (3)0.2990 (2)0.75696 (18)0.0634 (6)
H121.0360.38060.7010.076*
C130.7820 (3)0.3771 (2)0.8814 (2)0.0724 (6)
H13A0.8120.32420.92790.087*
H13B0.87570.37830.82430.087*
C140.7739 (3)0.5465 (3)0.9474 (2)0.0916 (9)
H14A0.69690.54661.01140.137*
H14B0.89120.60710.96870.137*
H14C0.72830.59460.90460.137*
C150.3199 (2)0.1663 (2)0.68137 (16)0.0534 (5)
C160.1146 (3)0.2014 (3)0.5798 (2)0.0708 (6)
H16A0.17410.31250.5940.106*
H16B0.07330.15840.50710.106*
H16C0.0150.19310.63130.106*
C170.3561 (2)0.2128 (2)0.54130 (16)0.0515 (5)
C180.3410 (3)0.4695 (2)0.4141 (2)0.0817 (7)
H18A0.31370.43670.35650.122*
H18B0.41160.54920.38440.122*
H18C0.23240.51430.44790.122*
N10.6195 (2)0.2883 (2)0.83366 (16)0.0742 (6)
O10.60740 (14)0.11333 (13)0.65328 (10)0.0479 (3)
O20.20954 (19)0.21669 (18)0.52121 (14)0.0846 (6)
O30.43951 (17)0.33142 (14)0.49437 (12)0.0686 (5)
O40.2979 (2)0.28477 (18)0.75497 (13)0.0838 (5)
O50.23681 (16)0.11152 (15)0.59040 (11)0.0609 (4)
H10.537 (3)0.336 (2)0.8373 (17)0.064 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0411 (8)0.0495 (9)0.0501 (11)0.0133 (7)0.0108 (7)0.0131 (8)
C20.0470 (9)0.0494 (9)0.0483 (11)0.0152 (8)0.0082 (8)0.0119 (8)
C30.0487 (9)0.0482 (9)0.0513 (11)0.0152 (8)0.0127 (8)0.0073 (8)
C40.0461 (9)0.0465 (9)0.0492 (11)0.0092 (8)0.0128 (8)0.0091 (8)
C50.0442 (9)0.0483 (9)0.0542 (11)0.0092 (8)0.0160 (8)0.0086 (8)
C60.0481 (9)0.0500 (9)0.0579 (12)0.0077 (8)0.0206 (8)0.0087 (8)
C70.0420 (9)0.0510 (9)0.0548 (11)0.0084 (8)0.0094 (8)0.0172 (8)
C80.0567 (11)0.0590 (11)0.0626 (13)0.0142 (9)0.0187 (9)0.0111 (9)
C90.0620 (12)0.0817 (14)0.0804 (16)0.0096 (11)0.0341 (11)0.0188 (12)
C100.0597 (12)0.0907 (16)0.1024 (19)0.0229 (12)0.0283 (12)0.0360 (14)
C110.0670 (13)0.0665 (12)0.1064 (19)0.0251 (11)0.0200 (13)0.0242 (13)
C120.0577 (11)0.0531 (11)0.0789 (15)0.0161 (9)0.0192 (10)0.0116 (10)
C130.0642 (12)0.0552 (11)0.0805 (16)0.0079 (10)0.0182 (11)0.0019 (11)
C140.0870 (16)0.0621 (13)0.098 (2)0.0124 (12)0.0179 (15)0.0113 (13)
C150.0512 (10)0.0526 (10)0.0585 (12)0.0183 (8)0.0103 (9)0.0127 (9)
C160.0646 (12)0.0770 (13)0.0857 (16)0.0344 (11)0.0181 (11)0.0262 (12)
C170.0541 (10)0.0465 (9)0.0572 (12)0.0145 (8)0.0172 (9)0.0129 (8)
C180.0937 (16)0.0485 (11)0.0919 (17)0.0120 (11)0.0452 (14)0.0039 (11)
N10.0693 (11)0.0582 (10)0.0843 (14)0.0273 (9)0.0337 (10)0.0118 (9)
O10.0445 (6)0.0438 (6)0.0551 (8)0.0136 (5)0.0164 (5)0.0076 (5)
O20.0726 (9)0.0722 (9)0.1049 (13)0.0284 (8)0.0511 (9)0.0031 (9)
O30.0643 (8)0.0439 (7)0.0885 (11)0.0160 (6)0.0324 (7)0.0040 (7)
O40.1029 (11)0.0753 (10)0.0763 (11)0.0557 (9)0.0302 (9)0.0072 (8)
O50.0608 (8)0.0616 (8)0.0675 (9)0.0279 (6)0.0203 (7)0.0131 (7)
Geometric parameters (Å, º) top
C1—C21.357 (2)C11—H110.93
C1—O11.358 (2)C12—H120.93
C1—C171.477 (2)C13—N11.410 (3)
C2—C31.432 (2)C13—C141.494 (3)
C2—C151.474 (2)C13—H13A0.97
C3—C41.371 (2)C13—H13B0.97
C3—N11.373 (2)C14—H14A0.96
C4—O11.378 (2)C14—H14B0.96
C4—C51.438 (2)C14—H14C0.96
C5—C61.326 (3)C15—O41.204 (2)
C5—H50.93C15—O51.310 (2)
C6—C71.457 (2)C16—O51.441 (2)
C6—H60.93C16—H16A0.96
C7—C121.379 (3)C16—H16B0.96
C7—C81.390 (2)C16—H16C0.96
C8—C91.375 (3)C17—O21.191 (2)
C8—H80.93C17—O31.320 (2)
C9—C101.368 (3)C18—O31.446 (2)
C9—H90.93C18—H18A0.96
C10—C111.363 (3)C18—H18B0.96
C10—H100.93C18—H18C0.96
C11—C121.375 (3)N1—H10.84 (2)
C2—C1—O1110.18 (14)N1—C13—C14112.23 (19)
C2—C1—C17134.44 (15)N1—C13—H13A109.2
O1—C1—C17115.28 (15)C14—C13—H13A109.2
C1—C2—C3106.67 (15)N1—C13—H13B109.2
C1—C2—C15130.78 (15)C14—C13—H13B109.2
C3—C2—C15122.55 (15)H13A—C13—H13B107.9
C4—C3—N1129.04 (16)C13—C14—H14A109.5
C4—C3—C2106.41 (15)C13—C14—H14B109.5
N1—C3—C2124.54 (16)H14A—C14—H14B109.5
C3—C4—O1109.05 (14)C13—C14—H14C109.5
C3—C4—C5134.99 (16)H14A—C14—H14C109.5
O1—C4—C5115.89 (15)H14B—C14—H14C109.5
C6—C5—C4125.55 (16)O4—C15—O5123.50 (17)
C6—C5—H5117.2O4—C15—C2122.64 (17)
C4—C5—H5117.2O5—C15—C2113.82 (16)
C5—C6—C7127.77 (16)O5—C16—H16A109.5
C5—C6—H6116.1O5—C16—H16B109.5
C7—C6—H6116.1H16A—C16—H16B109.5
C12—C7—C8117.15 (17)O5—C16—H16C109.5
C12—C7—C6119.89 (16)H16A—C16—H16C109.5
C8—C7—C6122.95 (17)H16B—C16—H16C109.5
C9—C8—C7120.62 (19)O2—C17—O3123.65 (16)
C9—C8—H8119.7O2—C17—C1124.69 (17)
C7—C8—H8119.7O3—C17—C1111.61 (15)
C10—C9—C8120.87 (19)O3—C18—H18A109.5
C10—C9—H9119.6O3—C18—H18B109.5
C8—C9—H9119.6H18A—C18—H18B109.5
C11—C10—C9119.44 (19)O3—C18—H18C109.5
C11—C10—H10120.3H18A—C18—H18C109.5
C9—C10—H10120.3H18B—C18—H18C109.5
C10—C11—C12119.9 (2)C3—N1—C13126.15 (18)
C10—C11—H11120.1C3—N1—H1112.2 (13)
C12—C11—H11120.1C13—N1—H1119.6 (13)
C11—C12—C7122.05 (19)C1—O1—C4107.68 (13)
C11—C12—H12119C17—O3—C18115.27 (15)
C7—C12—H12119C15—O5—C16116.89 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O40.85 (2)2.14 (2)2.813 (3)136.4 (18)
 

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