(E)-Dimethyl 4-butyl­amino-5-(4-methylstyr­yl)furan-2,3-dicarboxyl­ate

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.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](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

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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-butylamino-5-(4-methylstyryl)furan-2,3-dicarboxylate

Crystal data

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) Å^3

Data collection

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

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) + (0.0923P)^2] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.056	(Δ/σ)max < 0.001
wR(F^2) = 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+0.001xFc^2λ^3/sin(2θ)]^-1/4
253 parameters	Extinction coefficient: 0.014 (4)
0 restraints

Special details

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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