(E)-Dimethyl 4-(ethyl­amino)-5-styrylfuran-2,3-dicarboxyl­ate

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.

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

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

Crystal data

C18H19NO5	Z = 2
Mr = 329.34	F(000) = 348
Triclinic, P1	Dx = 1.313 Mg m^−3
Hall symbol: -P 1	Melting point = 391–392 K
a = 7.765 (4) Å	Mo Kα radiation, λ = 0.71075 Å
b = 9.043 (4) Å	Cell parameters from 5627 reflections
c = 13.044 (11) Å	θ = 3.1–27.5°
α = 70.17 (3)°	µ = 0.10 mm^−1
β = 82.36 (3)°	T = 298 K
γ = 75.52 (3)°	Needle, orange
V = 833.1 (9) Å^3	0.57 × 0.18 × 0.16 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	Rint = 0.027
Detector resolution: 10.00 pixels mm^-1	θmax = 27.5°, θmin = 3.1°
ω scans	h = −9→10
8262 measured reflections	k = −11→11
3772 independent reflections	l = −16→16
2119 reflections with I > 2σ(I)

Refinement

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0782P)^2] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.048	(Δ/σ)max < 0.001
wR(F^2) = 0.144	Δρmax = 0.26 e Å^−3
S = 0.99	Δρmin = −0.27 e Å^−3
3772 reflections	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
225 parameters	Extinction coefficient: 0.032 (6)
0 restraints

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.4641 (2)	0.0790 (2)	0.62418 (14)	0.0462 (4)
C2	0.4491 (2)	−0.0730 (2)	0.68415 (14)	0.0478 (4)
C3	0.5915 (2)	−0.1377 (2)	0.75712 (15)	0.0498 (5)
C4	0.6854 (2)	−0.0196 (2)	0.73558 (15)	0.0481 (4)
C5	0.8351 (2)	−0.0030 (2)	0.78157 (15)	0.0498 (5)
H5	0.8893	−0.0913	0.8374	0.06*
C6	0.9023 (2)	0.1275 (2)	0.75108 (16)	0.0531 (5)
H6	0.8488	0.2135	0.6936	0.064*
C7	1.0501 (2)	0.1523 (2)	0.79683 (15)	0.0489 (4)
C8	1.1458 (2)	0.0342 (2)	0.88139 (16)	0.0598 (5)
H8	1.116	−0.0658	0.9111	0.072*
C9	1.2843 (3)	0.0638 (3)	0.9215 (2)	0.0748 (7)
H9	1.3478	−0.0168	0.9777	0.09*
C10	1.3300 (3)	0.2103 (3)	0.8799 (2)	0.0794 (7)
H10	1.4236	0.2294	0.9077	0.095*
C11	1.2372 (3)	0.3281 (3)	0.7974 (2)	0.0773 (7)
H11	1.2674	0.428	0.7685	0.093*
C12	1.0988 (3)	0.2990 (2)	0.75696 (18)	0.0634 (6)
H12	1.036	0.3806	0.701	0.076*
C13	0.7820 (3)	−0.3771 (2)	0.8814 (2)	0.0724 (6)
H13A	0.812	−0.3242	0.9279	0.087*
H13B	0.8757	−0.3783	0.8243	0.087*
C14	0.7739 (3)	−0.5465 (3)	0.9474 (2)	0.0916 (9)
H14A	0.6969	−0.5466	1.0114	0.137*
H14B	0.8912	−0.6071	0.9687	0.137*
H14C	0.7283	−0.5946	0.9046	0.137*
C15	0.3199 (2)	−0.1663 (2)	0.68137 (16)	0.0534 (5)
C16	0.1146 (3)	−0.2014 (3)	0.5798 (2)	0.0708 (6)
H16A	0.1741	−0.3125	0.594	0.106*
H16B	0.0733	−0.1584	0.5071	0.106*
H16C	0.015	−0.1931	0.6313	0.106*
C17	0.3561 (2)	0.2128 (2)	0.54130 (16)	0.0515 (5)
C18	0.3410 (3)	0.4695 (2)	0.4141 (2)	0.0817 (7)
H18A	0.3137	0.4367	0.3565	0.122*
H18B	0.4116	0.5492	0.3844	0.122*
H18C	0.2324	0.5143	0.4479	0.122*
N1	0.6195 (2)	−0.2883 (2)	0.83366 (16)	0.0742 (6)
O1	0.60740 (14)	0.11333 (13)	0.65328 (10)	0.0479 (3)
O2	0.20954 (19)	0.21669 (18)	0.52121 (14)	0.0846 (6)
O3	0.43951 (17)	0.33142 (14)	0.49437 (12)	0.0686 (5)
O4	0.2979 (2)	−0.28477 (18)	0.75497 (13)	0.0838 (5)
O5	0.23681 (16)	−0.11152 (15)	0.59040 (11)	0.0609 (4)
H1	0.537 (3)	−0.336 (2)	0.8373 (17)	0.064 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0411 (8)	0.0495 (9)	0.0501 (11)	−0.0133 (7)	−0.0108 (7)	−0.0131 (8)
C2	0.0470 (9)	0.0494 (9)	0.0483 (11)	−0.0152 (8)	−0.0082 (8)	−0.0119 (8)
C3	0.0487 (9)	0.0482 (9)	0.0513 (11)	−0.0152 (8)	−0.0127 (8)	−0.0073 (8)
C4	0.0461 (9)	0.0465 (9)	0.0492 (11)	−0.0092 (8)	−0.0128 (8)	−0.0091 (8)
C5	0.0442 (9)	0.0483 (9)	0.0542 (11)	−0.0092 (8)	−0.0160 (8)	−0.0086 (8)
C6	0.0481 (9)	0.0500 (9)	0.0579 (12)	−0.0077 (8)	−0.0206 (8)	−0.0087 (8)
C7	0.0420 (9)	0.0510 (9)	0.0548 (11)	−0.0084 (8)	−0.0094 (8)	−0.0172 (8)
C8	0.0567 (11)	0.0590 (11)	0.0626 (13)	−0.0142 (9)	−0.0187 (9)	−0.0111 (9)
C9	0.0620 (12)	0.0817 (14)	0.0804 (16)	−0.0096 (11)	−0.0341 (11)	−0.0188 (12)
C10	0.0597 (12)	0.0907 (16)	0.1024 (19)	−0.0229 (12)	−0.0283 (12)	−0.0360 (14)
C11	0.0670 (13)	0.0665 (12)	0.1064 (19)	−0.0251 (11)	−0.0200 (13)	−0.0242 (13)
C12	0.0577 (11)	0.0531 (11)	0.0789 (15)	−0.0161 (9)	−0.0192 (10)	−0.0116 (10)
C13	0.0642 (12)	0.0552 (11)	0.0805 (16)	−0.0079 (10)	−0.0182 (11)	0.0019 (11)
C14	0.0870 (16)	0.0621 (13)	0.098 (2)	−0.0124 (12)	−0.0179 (15)	0.0113 (13)
C15	0.0512 (10)	0.0526 (10)	0.0585 (12)	−0.0183 (8)	−0.0103 (9)	−0.0127 (9)
C16	0.0646 (12)	0.0770 (13)	0.0857 (16)	−0.0344 (11)	−0.0181 (11)	−0.0262 (12)
C17	0.0541 (10)	0.0465 (9)	0.0572 (12)	−0.0145 (8)	−0.0172 (9)	−0.0129 (8)
C18	0.0937 (16)	0.0485 (11)	0.0919 (17)	−0.0120 (11)	−0.0452 (14)	0.0039 (11)
N1	0.0693 (11)	0.0582 (10)	0.0843 (14)	−0.0273 (9)	−0.0337 (10)	0.0118 (9)
O1	0.0445 (6)	0.0438 (6)	0.0551 (8)	−0.0136 (5)	−0.0164 (5)	−0.0076 (5)
O2	0.0726 (9)	0.0722 (9)	0.1049 (13)	−0.0284 (8)	−0.0511 (9)	0.0031 (9)
O3	0.0643 (8)	0.0439 (7)	0.0885 (11)	−0.0160 (6)	−0.0324 (7)	0.0040 (7)
O4	0.1029 (11)	0.0753 (10)	0.0763 (11)	−0.0557 (9)	−0.0302 (9)	0.0072 (8)
O5	0.0608 (8)	0.0616 (8)	0.0675 (9)	−0.0279 (6)	−0.0203 (7)	−0.0131 (7)

Geometric parameters (Å, º)

C1—C2	1.357 (2)	C11—H11	0.93
C1—O1	1.358 (2)	C12—H12	0.93
C1—C17	1.477 (2)	C13—N1	1.410 (3)
C2—C3	1.432 (2)	C13—C14	1.494 (3)
C2—C15	1.474 (2)	C13—H13A	0.97
C3—C4	1.371 (2)	C13—H13B	0.97
C3—N1	1.373 (2)	C14—H14A	0.96
C4—O1	1.378 (2)	C14—H14B	0.96
C4—C5	1.438 (2)	C14—H14C	0.96
C5—C6	1.326 (3)	C15—O4	1.204 (2)
C5—H5	0.93	C15—O5	1.310 (2)
C6—C7	1.457 (2)	C16—O5	1.441 (2)
C6—H6	0.93	C16—H16A	0.96
C7—C12	1.379 (3)	C16—H16B	0.96
C7—C8	1.390 (2)	C16—H16C	0.96
C8—C9	1.375 (3)	C17—O2	1.191 (2)
C8—H8	0.93	C17—O3	1.320 (2)
C9—C10	1.368 (3)	C18—O3	1.446 (2)
C9—H9	0.93	C18—H18A	0.96
C10—C11	1.363 (3)	C18—H18B	0.96
C10—H10	0.93	C18—H18C	0.96
C11—C12	1.375 (3)	N1—H1	0.84 (2)
C2—C1—O1	110.18 (14)	N1—C13—C14	112.23 (19)
C2—C1—C17	134.44 (15)	N1—C13—H13A	109.2
O1—C1—C17	115.28 (15)	C14—C13—H13A	109.2
C1—C2—C3	106.67 (15)	N1—C13—H13B	109.2
C1—C2—C15	130.78 (15)	C14—C13—H13B	109.2
C3—C2—C15	122.55 (15)	H13A—C13—H13B	107.9
C4—C3—N1	129.04 (16)	C13—C14—H14A	109.5
C4—C3—C2	106.41 (15)	C13—C14—H14B	109.5
N1—C3—C2	124.54 (16)	H14A—C14—H14B	109.5
C3—C4—O1	109.05 (14)	C13—C14—H14C	109.5
C3—C4—C5	134.99 (16)	H14A—C14—H14C	109.5
O1—C4—C5	115.89 (15)	H14B—C14—H14C	109.5
C6—C5—C4	125.55 (16)	O4—C15—O5	123.50 (17)
C6—C5—H5	117.2	O4—C15—C2	122.64 (17)
C4—C5—H5	117.2	O5—C15—C2	113.82 (16)
C5—C6—C7	127.77 (16)	O5—C16—H16A	109.5
C5—C6—H6	116.1	O5—C16—H16B	109.5
C7—C6—H6	116.1	H16A—C16—H16B	109.5
C12—C7—C8	117.15 (17)	O5—C16—H16C	109.5
C12—C7—C6	119.89 (16)	H16A—C16—H16C	109.5
C8—C7—C6	122.95 (17)	H16B—C16—H16C	109.5
C9—C8—C7	120.62 (19)	O2—C17—O3	123.65 (16)
C9—C8—H8	119.7	O2—C17—C1	124.69 (17)
C7—C8—H8	119.7	O3—C17—C1	111.61 (15)
C10—C9—C8	120.87 (19)	O3—C18—H18A	109.5
C10—C9—H9	119.6	O3—C18—H18B	109.5
C8—C9—H9	119.6	H18A—C18—H18B	109.5
C11—C10—C9	119.44 (19)	O3—C18—H18C	109.5
C11—C10—H10	120.3	H18A—C18—H18C	109.5
C9—C10—H10	120.3	H18B—C18—H18C	109.5
C10—C11—C12	119.9 (2)	C3—N1—C13	126.15 (18)
C10—C11—H11	120.1	C3—N1—H1	112.2 (13)
C12—C11—H11	120.1	C13—N1—H1	119.6 (13)
C11—C12—C7	122.05 (19)	C1—O1—C4	107.68 (13)
C11—C12—H12	119	C17—O3—C18	115.27 (15)
C7—C12—H12	119	C15—O5—C16	116.89 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4	0.85 (2)	2.14 (2)	2.813 (3)	136.4 (18)