Dimethyl 2-(4-fluoro­phen­yl)-3-(methyl­amino)furan-4,5-dicarboxyl­ate

The title compound, C₁₅H₁₄FNO₅, was synthesized via a thia­zole–carbene-mediated multicomponent reaction. In the crystal structure, the dihedral angle between the benzene and furan rings is 17.58 (11)°. Non-classical C—H...O hydrogen bonds link the mol­ecules in the crystal structure into infinite chains.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C)= 0.003 Å
• R factor = 0.049
• wR factor = 0.147
• Data-to-parameter ratio = 16.4

checkCIF/PLATON results

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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: CRYSTALS (Watkin, 1996); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure and PLATON (Spek, 2003).

Dimethyl 2-(4-fluorophenyl)-3-(methylamino)furan-4,5-dicarboxylate

Crystal data

C15H14FNO5	F(000) = 1280.00
Mr = 307.28	Dx = 1.420 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -C 2yc	Cell parameters from 8846 reflections
a = 17.3249 (8) Å	θ = 2.6–27.4°
b = 9.4165 (4) Å	µ = 0.12 mm^−1
c = 18.2202 (10) Å	T = 295 K
β = 104.7530 (6)°	Prism, yellow
V = 2874.4 (2) Å^3	0.60 × 0.48 × 0.46 mm
Z = 8

Data collection

Rigaku R-AXIS RAPID diffractometer	1935 reflections with F^2 > 2σ(F^2)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.031
ω scans	θmax = 27.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −22→22
Tmin = 0.914, Tmax = 0.948	k = −12→12
12161 measured reflections	l = −23→21
3283 independent reflections

Refinement

Refinement on F^2	w = 1/[0.0017Fo^2 + σ(Fo^2)]/(4Fo^2)
R[F^2 > 2σ(F^2)] = 0.049	(Δ/σ)max < 0.001
wR(F^2) = 0.147	Δρmax = 0.48 e Å^−3
S = 1.01	Δρmin = −0.34 e Å^−3
3283 reflections	Extinction correction: Larson (1970), equation 22
200 parameters	Extinction coefficient: 19 (2)
H-atom parameters constrained

Special details

Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
F1	0.69423 (8)	−0.21002 (14)	0.58703 (9)	0.0790 (4)
O1	0.46131 (6)	0.16041 (13)	0.33862 (6)	0.0441 (3)
O2	0.45884 (11)	0.64370 (18)	0.36224 (10)	0.0760 (5)
O3	0.39961 (9)	0.56899 (16)	0.24586 (8)	0.0594 (4)
O4	0.29565 (9)	0.32880 (18)	0.22048 (9)	0.0669 (5)
O5	0.34847 (9)	0.11257 (17)	0.21684 (9)	0.0599 (4)
N1	0.56956 (10)	0.44245 (19)	0.45356 (10)	0.0502 (4)
C1	0.52017 (11)	0.2073 (2)	0.39952 (11)	0.0405 (5)
C2	0.51895 (11)	0.3534 (2)	0.40074 (11)	0.0413 (5)
C3	0.45537 (11)	0.3971 (2)	0.33759 (11)	0.0420 (5)
C4	0.42177 (11)	0.2755 (2)	0.30266 (11)	0.0439 (5)
C5	0.56589 (11)	0.0987 (2)	0.44833 (11)	0.0403 (5)
C6	0.60956 (11)	0.1309 (2)	0.52186 (11)	0.0465 (5)
C7	0.65243 (12)	0.0283 (2)	0.56900 (12)	0.0518 (6)
C8	0.65135 (12)	−0.1074 (2)	0.54128 (12)	0.0523 (6)
C9	0.60816 (12)	−0.1450 (2)	0.47039 (13)	0.0570 (6)
C10	0.56520 (12)	−0.0413 (2)	0.42394 (12)	0.0507 (5)
C11	0.43772 (12)	0.5475 (2)	0.31786 (12)	0.0454 (5)
C12	0.37734 (14)	0.7143 (2)	0.22470 (16)	0.0697 (7)
C13	0.34893 (12)	0.2453 (2)	0.24209 (12)	0.0469 (5)
C14	0.27777 (13)	0.0682 (2)	0.16062 (14)	0.0692 (7)
C15	0.65342 (12)	0.4449 (2)	0.45291 (13)	0.0619 (6)
H6	0.6079	0.2270	0.5406	0.054*
H7	0.6839	0.0521	0.6196	0.060*
H9	0.6082	−0.2423	0.4529	0.067*
H10	0.5341	−0.0657	0.3733	0.058*
H101	0.5383	0.5298	0.4499	0.059*
H131	0.3245	0.7341	0.2311	0.084*
H132	0.3776	0.7288	0.1721	0.084*
H133	0.4158	0.7776	0.2567	0.084*
H151	0.2404	0.0272	0.1862	0.079*
H152	0.2916	−0.0020	0.1272	0.079*
H153	0.2535	0.1498	0.1311	0.079*
H161	0.6820	0.3732	0.4876	0.072*
H162	0.6766	0.5374	0.4682	0.072*
H163	0.6574	0.4239	0.4019	0.072*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0792 (9)	0.0629 (9)	0.0818 (9)	0.0166 (7)	−0.0036 (7)	0.0252 (7)
O1	0.0430 (7)	0.0401 (7)	0.0440 (7)	−0.0013 (5)	0.0017 (5)	0.0027 (6)
O2	0.1106 (14)	0.0465 (9)	0.0619 (10)	0.0159 (9)	0.0056 (9)	−0.0068 (8)
O3	0.0720 (10)	0.0447 (9)	0.0547 (9)	0.0015 (7)	0.0035 (7)	0.0089 (7)
O4	0.0521 (8)	0.0565 (9)	0.0782 (11)	0.0074 (8)	−0.0088 (8)	0.0027 (8)
O5	0.0528 (8)	0.0566 (9)	0.0601 (9)	0.0016 (7)	−0.0045 (7)	−0.0109 (7)
N1	0.0520 (10)	0.0424 (9)	0.0513 (10)	0.0012 (8)	0.0039 (7)	−0.0065 (8)
C1	0.0390 (9)	0.0426 (11)	0.0380 (10)	−0.0004 (8)	0.0063 (8)	−0.0003 (8)
C2	0.0418 (10)	0.0393 (11)	0.0418 (10)	0.0008 (8)	0.0091 (8)	−0.0007 (8)
C3	0.0423 (10)	0.0425 (11)	0.0415 (11)	0.0023 (8)	0.0114 (8)	0.0024 (9)
C4	0.0400 (9)	0.0425 (11)	0.0472 (11)	0.0038 (8)	0.0077 (8)	0.0072 (9)
C5	0.0369 (9)	0.0372 (10)	0.0454 (10)	0.0002 (8)	0.0077 (8)	0.0002 (8)
C6	0.0493 (11)	0.0423 (11)	0.0446 (11)	−0.0008 (9)	0.0060 (9)	−0.0027 (9)
C7	0.0497 (11)	0.0550 (14)	0.0440 (11)	−0.0031 (10)	−0.0004 (9)	0.0046 (10)
C8	0.0467 (11)	0.0479 (12)	0.0573 (13)	0.0072 (9)	0.0039 (9)	0.0163 (10)
C9	0.0645 (13)	0.0372 (12)	0.0651 (14)	0.0041 (9)	0.0085 (11)	−0.0008 (10)
C10	0.0531 (12)	0.0416 (11)	0.0494 (11)	0.0016 (9)	−0.0013 (9)	−0.0021 (10)
C11	0.0473 (11)	0.0446 (11)	0.0455 (11)	0.0053 (9)	0.0142 (9)	0.0036 (10)
C12	0.0748 (16)	0.0541 (14)	0.0773 (17)	0.0106 (12)	0.0140 (13)	0.0249 (13)
C13	0.0460 (11)	0.0480 (13)	0.0434 (11)	−0.0010 (10)	0.0055 (9)	0.0076 (9)
C14	0.0550 (13)	0.0730 (17)	0.0681 (15)	−0.0044 (12)	−0.0052 (11)	−0.0130 (13)
C15	0.0536 (12)	0.0585 (14)	0.0653 (14)	−0.0101 (11)	0.0003 (10)	−0.0000 (12)

Geometric parameters (Å, º)

F1—C8	1.366 (2)	C6—C7	1.378 (2)
O1—C1	1.375 (2)	C7—C8	1.372 (3)
O1—C4	1.358 (2)	C8—C9	1.364 (3)
O2—C11	1.208 (2)	C9—C10	1.380 (2)
O3—C11	1.325 (2)	N1—H101	0.977
O3—C12	1.447 (2)	C6—H6	0.970
O4—C13	1.200 (2)	C7—H7	0.970
O5—C13	1.332 (2)	C9—H9	0.970
O5—C14	1.444 (2)	C10—H10	0.970
N1—C2	1.403 (2)	C12—H131	0.970
N1—C15	1.456 (2)	C12—H132	0.970
C1—C2	1.376 (2)	C12—H133	0.970
C1—C5	1.451 (2)	C14—H151	0.970
C2—C3	1.435 (2)	C14—H152	0.970
C3—C4	1.366 (2)	C14—H153	0.970
C3—C11	1.474 (2)	C15—H161	0.970
C4—C13	1.477 (2)	C15—H162	0.970
C5—C6	1.394 (2)	C15—H163	0.970
C5—C10	1.390 (2)
C1—O1—C4	108.19 (14)	O4—C13—C4	124.0 (2)
C11—O3—C12	116.11 (17)	O5—C13—C4	111.56 (16)
C13—O5—C14	116.49 (17)	C2—N1—H101	102.5
C2—N1—C15	117.03 (18)	C15—N1—H101	121.5
O1—C1—C2	108.85 (15)	C5—C6—H6	119.0
O1—C1—C5	116.42 (16)	C7—C6—H6	119.6
C2—C1—C5	134.67 (16)	C6—C7—H7	120.9
N1—C2—C1	126.79 (16)	C8—C7—H7	121.1
N1—C2—C3	126.65 (17)	C8—C9—H9	120.7
C1—C2—C3	106.56 (15)	C10—C9—H9	120.9
C2—C3—C4	106.41 (16)	C5—C10—H10	119.1
C2—C3—C11	122.67 (16)	C9—C10—H10	119.8
C4—C3—C11	130.87 (16)	O3—C12—H131	110.2
O1—C4—C3	109.96 (14)	O3—C12—H132	109.2
O1—C4—C13	115.91 (16)	O3—C12—H133	109.0
C3—C4—C13	133.70 (18)	H131—C12—H132	109.5
C1—C5—C6	120.88 (17)	H131—C12—H133	109.5
C1—C5—C10	120.90 (16)	H132—C12—H133	109.5
C6—C5—C10	118.18 (17)	O5—C14—H151	108.9
C5—C6—C7	121.39 (19)	O5—C14—H152	110.0
C6—C7—C8	117.96 (18)	O5—C14—H153	109.5
F1—C8—C7	118.69 (18)	H151—C14—H152	109.5
F1—C8—C9	118.40 (19)	H151—C14—H153	109.5
C7—C8—C9	122.90 (19)	H152—C14—H153	109.5
C8—C9—C10	118.5 (2)	N1—C15—H161	109.2
C5—C10—C9	121.05 (18)	N1—C15—H162	110.6
O2—C11—O3	122.52 (19)	N1—C15—H163	108.6
O2—C11—C3	123.30 (18)	H161—C15—H162	109.5
O3—C11—C3	114.11 (17)	H161—C15—H163	109.5
O4—C13—O5	124.42 (17)	H162—C15—H163	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H101···O2	0.98	2.12	2.901 (3)	136
C7—H7···O4^i	0.97	2.56	3.478 (3)	157

Symmetry code: (i) x+1/2, −y+1/2, z+1/2.