The title compound, C21H25NO5, was synthesized via a thiazole carbene-mediated multicomponent reaction. Without π–π stacking or other weak intermolecular interactions, the crystal packing is controlled by van der Waals forces.
Supporting information
CCDC reference: 618224
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.003 Å
- R factor = 0.056
- wR factor = 0.187
- Data-to-parameter ratio = 17.9
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.52 Ratio
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.03 Ratio
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C5
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C18
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
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 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
0 ALERT type 5 Informative message, check
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-butylamino-5-(4-methylstyryl)furan-2,3-dicarboxylate
top
Crystal data top
C21H25NO5 | Z = 2 |
Mr = 371.42 | F(000) = 396 |
Triclinic, P1 | Dx = 1.229 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71075 Å |
a = 5.446 (3) Å | Cell parameters from 6175 reflections |
b = 10.454 (7) Å | θ = 3.3–27.5° |
c = 18.386 (12) Å | µ = 0.09 mm−1 |
α = 77.94 (3)° | T = 298 K |
β = 88.97 (2)° | Prism, orange |
γ = 78.68 (2)° | 0.4 × 0.35 × 0.12 mm |
V = 1003.5 (11) Å3 | |
Data collection top
Rigaku R-AXIS RAPID diffractometer | Rint = 0.033 |
Detector resolution: 10.00 pixels mm-1 | θmax = 27.5°, θmin = 3.4° |
ω scans | h = −6→6 |
9965 measured reflections | k = −13→13 |
4536 independent reflections | l = −23→23 |
2368 reflections with I > 2σ(I) | |
Refinement top
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0923P)2] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.056 | (Δ/σ)max < 0.001 |
wR(F2) = 0.187 | Δρmax = 0.22 e Å−3 |
S = 1.07 | Δρmin = −0.25 e Å−3 |
4536 reflections | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
253 parameters | Extinction coefficient: 0.014 (4) |
0 restraints | |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
N1 | 0.0208 (4) | 0.1852 (2) | 0.23010 (11) | 0.0643 (6) | |
O1 | 0.5302 (2) | 0.07593 (14) | 0.36235 (8) | 0.0521 (4) | |
O2 | 0.7095 (3) | 0.12529 (18) | 0.47732 (9) | 0.0683 (5) | |
O3 | 0.3671 (4) | 0.2607 (2) | 0.49970 (12) | 0.1023 (8) | |
O4 | −0.0159 (3) | 0.40111 (18) | 0.40422 (10) | 0.0791 (6) | |
O5 | −0.2237 (3) | 0.35838 (19) | 0.31329 (11) | 0.0836 (6) | |
C1 | 0.3838 (4) | 0.1723 (2) | 0.39088 (11) | 0.0507 (5) | |
C2 | 0.1744 (4) | 0.2268 (2) | 0.34706 (11) | 0.0507 (5) | |
C3 | 0.1926 (4) | 0.1574 (2) | 0.28668 (11) | 0.0509 (5) | |
C4 | 0.4148 (4) | 0.0652 (2) | 0.29842 (11) | 0.0506 (5) | |
C5 | 0.4793 (4) | 0.1939 (2) | 0.46097 (13) | 0.0563 (6) | |
C6 | 0.8236 (5) | 0.1403 (3) | 0.54386 (13) | 0.0706 (7) | |
H6A | 0.8771 | 0.2243 | 0.5349 | 0.106* | |
H6B | 0.9658 | 0.0692 | 0.5582 | 0.106* | |
H6C | 0.7044 | 0.1376 | 0.583 | 0.106* | |
C7 | −0.0411 (4) | 0.3351 (2) | 0.35261 (13) | 0.0559 (6) | |
C8 | −0.2234 (6) | 0.5063 (3) | 0.41290 (17) | 0.0906 (9) | |
H8A | −0.2561 | 0.5706 | 0.3668 | 0.136* | |
H8B | −0.1823 | 0.549 | 0.4512 | 0.136* | |
H8C | −0.3696 | 0.469 | 0.4264 | 0.136* | |
C9 | 0.0428 (4) | 0.1261 (2) | 0.16655 (12) | 0.0583 (6) | |
H9A | 0.0466 | 0.0312 | 0.1822 | 0.07* | |
H9B | 0.1989 | 0.1377 | 0.1422 | 0.07* | |
C10 | −0.1740 (4) | 0.1887 (3) | 0.11223 (13) | 0.0687 (7) | |
H10A | −0.3294 | 0.1805 | 0.1377 | 0.082* | |
H10B | −0.1734 | 0.2831 | 0.0958 | 0.082* | |
C11 | −0.1664 (6) | 0.1282 (4) | 0.04657 (17) | 0.1000 (10) | |
H11A | −0.1554 | 0.0329 | 0.0635 | 0.12* | |
H11B | −0.0147 | 0.1411 | 0.02 | 0.12* | |
C12 | −0.3835 (7) | 0.1810 (5) | −0.00650 (19) | 0.1274 (15) | |
H12A | −0.5316 | 0.1562 | 0.0166 | 0.191* | |
H12B | −0.3517 | 0.1444 | −0.0503 | 0.191* | |
H12C | −0.4072 | 0.2765 | −0.02 | 0.191* | |
C13 | 0.5398 (4) | −0.0370 (2) | 0.26238 (11) | 0.0528 (5) | |
H13 | 0.4617 | −0.0475 | 0.2201 | 0.063* | |
C14 | 0.7595 (4) | −0.1191 (2) | 0.28394 (12) | 0.0565 (6) | |
H14 | 0.8354 | −0.1089 | 0.3267 | 0.068* | |
C15 | 0.8913 (4) | −0.2224 (2) | 0.24745 (12) | 0.0548 (6) | |
C16 | 0.8000 (4) | −0.2538 (3) | 0.18531 (14) | 0.0719 (7) | |
H16 | 0.6446 | −0.2076 | 0.165 | 0.086* | |
C17 | 0.9335 (5) | −0.3520 (3) | 0.15284 (16) | 0.0801 (8) | |
H17 | 0.8673 | −0.3693 | 0.1105 | 0.096* | |
C18 | 1.1616 (5) | −0.4252 (2) | 0.18099 (16) | 0.0700 (7) | |
C19 | 1.2527 (5) | −0.3964 (3) | 0.24272 (18) | 0.0824 (8) | |
H19 | 1.4058 | −0.4451 | 0.2635 | 0.099* | |
C20 | 1.1226 (4) | −0.2963 (3) | 0.27523 (16) | 0.0764 (8) | |
H20 | 1.1921 | −0.278 | 0.3168 | 0.092* | |
C21 | 1.3072 (6) | −0.5352 (3) | 0.1462 (2) | 0.1036 (11) | |
H21A | 1.4771 | −0.5234 | 0.1393 | 0.155* | |
H21B | 1.2316 | −0.5318 | 0.0988 | 0.155* | |
H21C | 1.3052 | −0.6202 | 0.1782 | 0.155* | |
H1 | −0.111 (5) | 0.243 (3) | 0.2379 (14) | 0.085 (8)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0552 (11) | 0.0757 (14) | 0.0579 (11) | 0.0121 (10) | −0.0141 (9) | −0.0269 (10) |
O1 | 0.0476 (7) | 0.0555 (9) | 0.0527 (8) | 0.0011 (6) | −0.0023 (6) | −0.0204 (7) |
O2 | 0.0566 (9) | 0.0863 (12) | 0.0589 (9) | 0.0073 (8) | −0.0134 (7) | −0.0270 (8) |
O3 | 0.0809 (12) | 0.1262 (18) | 0.1041 (15) | 0.0303 (11) | −0.0237 (10) | −0.0792 (14) |
O4 | 0.0841 (11) | 0.0669 (11) | 0.0794 (12) | 0.0234 (9) | −0.0128 (9) | −0.0343 (9) |
O5 | 0.0583 (9) | 0.0871 (13) | 0.1023 (14) | 0.0191 (9) | −0.0205 (9) | −0.0421 (11) |
C1 | 0.0491 (11) | 0.0509 (12) | 0.0520 (12) | −0.0028 (9) | 0.0007 (9) | −0.0167 (10) |
C2 | 0.0465 (11) | 0.0524 (13) | 0.0523 (12) | −0.0029 (9) | 0.0005 (9) | −0.0152 (10) |
C3 | 0.0481 (11) | 0.0521 (12) | 0.0510 (12) | −0.0017 (9) | −0.0003 (9) | −0.0149 (10) |
C4 | 0.0479 (10) | 0.0584 (13) | 0.0439 (11) | −0.0024 (9) | −0.0045 (9) | −0.0143 (9) |
C5 | 0.0510 (11) | 0.0607 (14) | 0.0603 (13) | −0.0061 (10) | −0.0025 (10) | −0.0241 (11) |
C6 | 0.0686 (14) | 0.0851 (18) | 0.0582 (14) | −0.0101 (12) | −0.0135 (11) | −0.0188 (13) |
C7 | 0.0522 (12) | 0.0534 (13) | 0.0585 (13) | 0.0002 (9) | −0.0001 (10) | −0.0135 (11) |
C8 | 0.096 (2) | 0.0718 (18) | 0.092 (2) | 0.0285 (15) | −0.0021 (16) | −0.0325 (15) |
C9 | 0.0530 (11) | 0.0654 (14) | 0.0547 (13) | −0.0017 (10) | −0.0062 (10) | −0.0169 (11) |
C10 | 0.0587 (13) | 0.0840 (18) | 0.0608 (14) | −0.0008 (12) | −0.0079 (11) | −0.0210 (13) |
C11 | 0.094 (2) | 0.134 (3) | 0.0739 (19) | −0.0046 (18) | −0.0197 (15) | −0.0394 (19) |
C12 | 0.110 (3) | 0.197 (4) | 0.075 (2) | −0.034 (3) | −0.0369 (19) | −0.022 (2) |
C13 | 0.0524 (11) | 0.0574 (13) | 0.0472 (11) | −0.0007 (9) | −0.0043 (9) | −0.0166 (10) |
C14 | 0.0550 (11) | 0.0575 (13) | 0.0562 (13) | 0.0003 (10) | −0.0073 (10) | −0.0199 (10) |
C15 | 0.0485 (11) | 0.0553 (13) | 0.0579 (13) | 0.0008 (9) | −0.0050 (10) | −0.0156 (10) |
C16 | 0.0628 (13) | 0.0747 (17) | 0.0757 (17) | 0.0115 (12) | −0.0140 (12) | −0.0323 (14) |
C17 | 0.0778 (16) | 0.0861 (19) | 0.0797 (18) | 0.0029 (14) | −0.0043 (14) | −0.0423 (15) |
C18 | 0.0637 (14) | 0.0540 (14) | 0.0904 (19) | −0.0006 (11) | 0.0140 (13) | −0.0220 (13) |
C19 | 0.0566 (13) | 0.0745 (18) | 0.108 (2) | 0.0155 (12) | −0.0076 (14) | −0.0275 (16) |
C20 | 0.0578 (13) | 0.0798 (18) | 0.0873 (18) | 0.0142 (12) | −0.0179 (12) | −0.0324 (15) |
C21 | 0.100 (2) | 0.076 (2) | 0.139 (3) | −0.0017 (16) | 0.032 (2) | −0.0466 (19) |
Geometric parameters (Å, º) top
N1—C3 | 1.358 (3) | C10—H10A | 0.97 |
N1—C9 | 1.424 (3) | C10—H10B | 0.97 |
N1—H1 | 0.87 (3) | C11—C12 | 1.488 (4) |
O1—C1 | 1.348 (2) | C11—H11A | 0.97 |
O1—C4 | 1.378 (3) | C11—H11B | 0.97 |
O2—C5 | 1.322 (3) | C12—H12A | 0.96 |
O2—C6 | 1.433 (3) | C12—H12B | 0.96 |
O3—C5 | 1.180 (3) | C12—H12C | 0.96 |
O4—C7 | 1.308 (3) | C13—C14 | 1.340 (3) |
O4—C8 | 1.446 (3) | C13—H13 | 0.93 |
O5—C7 | 1.195 (3) | C14—C15 | 1.454 (3) |
C1—C2 | 1.364 (3) | C14—H14 | 0.93 |
C1—C5 | 1.474 (3) | C15—C16 | 1.379 (3) |
C2—C3 | 1.439 (3) | C15—C20 | 1.386 (3) |
C2—C7 | 1.481 (3) | C16—C17 | 1.373 (3) |
C3—C4 | 1.380 (3) | C16—H16 | 0.93 |
C4—C13 | 1.427 (3) | C17—C18 | 1.372 (4) |
C6—H6A | 0.96 | C17—H17 | 0.93 |
C6—H6B | 0.96 | C18—C19 | 1.359 (4) |
C6—H6C | 0.96 | C18—C21 | 1.514 (4) |
C8—H8A | 0.96 | C19—C20 | 1.382 (4) |
C8—H8B | 0.96 | C19—H19 | 0.93 |
C8—H8C | 0.96 | C20—H20 | 0.93 |
C9—C10 | 1.512 (3) | C21—H21A | 0.96 |
C9—H9A | 0.97 | C21—H21B | 0.96 |
C9—H9B | 0.97 | C21—H21C | 0.96 |
C10—C11 | 1.472 (4) | | |
| | | |
C3—N1—C9 | 125.54 (19) | C11—C10—H10B | 108.9 |
C3—N1—H1 | 111.4 (18) | C9—C10—H10B | 108.9 |
C9—N1—H1 | 123.0 (19) | H10A—C10—H10B | 107.7 |
C1—O1—C4 | 108.35 (16) | C10—C11—C12 | 115.6 (3) |
C5—O2—C6 | 116.41 (19) | C10—C11—H11A | 108.4 |
C7—O4—C8 | 116.8 (2) | C12—C11—H11A | 108.4 |
O1—C1—C2 | 110.34 (19) | C10—C11—H11B | 108.4 |
O1—C1—C5 | 114.98 (18) | C12—C11—H11B | 108.4 |
C2—C1—C5 | 134.67 (19) | H11A—C11—H11B | 107.4 |
C1—C2—C3 | 106.37 (18) | C11—C12—H12A | 109.5 |
C1—C2—C7 | 132.0 (2) | C11—C12—H12B | 109.5 |
C3—C2—C7 | 121.59 (19) | H12A—C12—H12B | 109.5 |
N1—C3—C4 | 129.6 (2) | C11—C12—H12C | 109.5 |
N1—C3—C2 | 124.13 (18) | H12A—C12—H12C | 109.5 |
C4—C3—C2 | 106.24 (19) | H12B—C12—H12C | 109.5 |
O1—C4—C3 | 108.70 (18) | C14—C13—C4 | 126.0 (2) |
O1—C4—C13 | 115.90 (17) | C14—C13—H13 | 117 |
C3—C4—C13 | 135.3 (2) | C4—C13—H13 | 117 |
O3—C5—O2 | 122.8 (2) | C13—C14—C15 | 126.8 (2) |
O3—C5—C1 | 125.7 (2) | C13—C14—H14 | 116.6 |
O2—C5—C1 | 111.43 (19) | C15—C14—H14 | 116.6 |
O2—C6—H6A | 109.5 | C16—C15—C20 | 116.2 (2) |
O2—C6—H6B | 109.5 | C16—C15—C14 | 123.9 (2) |
H6A—C6—H6B | 109.5 | C20—C15—C14 | 119.9 (2) |
O2—C6—H6C | 109.5 | C17—C16—C15 | 121.4 (2) |
H6A—C6—H6C | 109.5 | C17—C16—H16 | 119.3 |
H6B—C6—H6C | 109.5 | C15—C16—H16 | 119.3 |
O5—C7—O4 | 123.3 (2) | C18—C17—C16 | 122.0 (3) |
O5—C7—C2 | 122.1 (2) | C18—C17—H17 | 119 |
O4—C7—C2 | 114.7 (2) | C16—C17—H17 | 119 |
O4—C8—H8A | 109.5 | C19—C18—C17 | 117.2 (2) |
O4—C8—H8B | 109.5 | C19—C18—C21 | 120.6 (3) |
H8A—C8—H8B | 109.5 | C17—C18—C21 | 122.2 (3) |
O4—C8—H8C | 109.5 | C18—C19—C20 | 121.4 (2) |
H8A—C8—H8C | 109.5 | C18—C19—H19 | 119.3 |
H8B—C8—H8C | 109.5 | C20—C19—H19 | 119.3 |
N1—C9—C10 | 110.97 (19) | C19—C20—C15 | 121.7 (3) |
N1—C9—H9A | 109.4 | C19—C20—H20 | 119.1 |
C10—C9—H9A | 109.4 | C15—C20—H20 | 119.1 |
N1—C9—H9B | 109.4 | C18—C21—H21A | 109.5 |
C10—C9—H9B | 109.4 | C18—C21—H21B | 109.5 |
H9A—C9—H9B | 108 | H21A—C21—H21B | 109.5 |
C11—C10—C9 | 113.5 (2) | C18—C21—H21C | 109.5 |
C11—C10—H10A | 108.9 | H21A—C21—H21C | 109.5 |
C9—C10—H10A | 108.9 | H21B—C21—H21C | 109.5 |