(S)-Methyl 2-[(furan-2-carbon­yl)amino]-3-phenyl­propanoate

Zeng, X.C.; Li, L.H.; Cen, Y.Z.

doi:10.1107/S160053680602335X

(S)-Methyl 2-[(furan-2-carbonyl)amino]-3-phenylpropanoate

The title compound, C₁₅H₁₅NO₄, was synthesized by acylation of methyl L-2-amino-3-phenylpropanoate with furan-2-carbonyl chloride at room temperature. In the crystal structure, intermolecular N—H

O hydrogen bonds link the molecules into extended chains parallel to the b axis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680602335X/sg2039sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680602335X/sg2039Isup2.hkl Contains datablock I

CCDC reference: 618323

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.003 Å
R factor = 0.029
wR factor = 0.073
Data-to-parameter ratio = 8.8

checkCIF/PLATON results

No syntax errors found



Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.00
           From the CIF: _reflns_number_total               1612
           Count of symmetry unique reflns         1614
           Completeness (_total/calc)             99.88%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   0 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

(I) top

Crystal data top

C₁₅H₁₅NO₄	D_x = 1.286 Mg m⁻³
M_r = 273.28	Melting point: 72 K
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3976 reflections
a = 8.5817 (12) Å	θ = 2.2–27.0°
b = 8.9505 (14) Å	µ = 0.09 mm⁻¹
c = 18.375 (3) Å	T = 173 K
V = 1411.4 (4) Å³	Block, colorless
Z = 4	0.48 × 0.46 × 0.32 mm
F(000) = 576

Data collection top

Bruker SMART 1K CCD area detector diffractometer	1612 independent reflections
Radiation source: fine-focus sealed tube	1492 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
φ and ω scans	θ_max = 26.0°, θ_min = 2.2°
Absorption correction: multi-scan SADABS (Sheldrick, 1996)	h = −5→10
T_min = 0.870, T_max = 0.971	k = −9→11
5884 measured reflections	l = −13→22

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.029	H-atom parameters constrained
wR(F²) = 0.073	w = 1/[σ²(F_o²) + (0.0353P)² + 0.265P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
1612 reflections	Δρ_max = 0.17 e Å⁻³
184 parameters	Δρ_min = −0.15 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.042 (3)

Special details top

Experimental. ¹H NMR (CDCl₃, 500 Hz): 7.46 (s, 1H, ArH), 7.33–7.26 (m, 3H, ArH), 7.17–7.14 (m, 3H, ArH), 6.80 (d, 1H, NH), 6.51 (q, 1H, ArH), 5.10–5.06 (m, 1H, CH), 3.77 (s, 3H, OCH₃), 3.28–3.21 (m, 2H, CH₂); IR(KBr): 3296(CONH), 3144 (Furan), 2949 (OCH₃), 1732 (CO), 1645 (CONH), 1595 (Ar), 1538 (Ar), 1255 (COOR), 1010 (COOR), 684 (C₆H₅).

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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.09374 (15)	0.12239 (14)	0.13118 (6)	0.0322 (3)
O2	−0.13344 (15)	−0.15011 (13)	0.22340 (7)	0.0310 (3)
O3	−0.1929 (2)	0.0712 (2)	0.44130 (8)	0.0620 (5)
O4	−0.20900 (16)	0.20787 (15)	0.33985 (7)	0.0376 (3)
N1	0.00184 (19)	0.04840 (16)	0.26745 (7)	0.0284 (3)
H1	0.0540	0.1300	0.2564	0.034*
C9	0.2653 (2)	−0.0545 (2)	0.36154 (9)	0.0301 (4)
C4	−0.0138 (2)	0.01052 (18)	0.13903 (9)	0.0267 (4)
C5	−0.05333 (19)	−0.03698 (19)	0.21376 (9)	0.0259 (4)
C3	−0.0666 (2)	−0.0346 (2)	0.07381 (9)	0.0313 (4)
H3	−0.1411	−0.1108	0.0648	0.038*
C1	0.1065 (2)	0.1463 (2)	0.05767 (10)	0.0372 (5)
H1A	0.1734	0.2180	0.0358	0.045*
C7	−0.1515 (2)	0.0981 (2)	0.38044 (10)	0.0362 (5)
C2	0.0112 (2)	0.0543 (2)	0.02102 (9)	0.0365 (4)
H2	−0.0018	0.0494	−0.0303	0.044*
C14	0.2772 (2)	−0.2051 (2)	0.37937 (10)	0.0357 (4)
H14	0.1953	−0.2525	0.4054	0.043*
C8	0.1287 (2)	0.0362 (2)	0.38723 (9)	0.0335 (4)
H8A	0.1565	0.1434	0.3847	0.040*
H8B	0.1082	0.0117	0.4389	0.040*
C6	−0.0216 (2)	0.0107 (2)	0.34340 (9)	0.0296 (4)
H6	−0.0483	−0.0979	0.3463	0.036*
C11	0.5156 (3)	−0.0695 (3)	0.30275 (11)	0.0509 (6)
H11	0.5969	−0.0226	0.2761	0.061*
C10	0.3851 (2)	0.0109 (3)	0.32230 (10)	0.0412 (5)
H10	0.3772	0.1130	0.3086	0.049*
C13	0.4076 (3)	−0.2863 (2)	0.35943 (13)	0.0487 (5)
H13	0.4148	−0.3893	0.3715	0.058*
C15	−0.3242 (2)	0.3003 (3)	0.37531 (13)	0.0495 (5)
H15A	−0.4115	0.2379	0.3914	0.074*
H15B	−0.3622	0.3759	0.3411	0.074*
H15C	−0.2772	0.3497	0.4175	0.074*
C12	0.5282 (3)	−0.2170 (3)	0.32178 (13)	0.0538 (6)
H12	0.6191	−0.2719	0.3093	0.065*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0347 (7)	0.0356 (7)	0.0261 (6)	−0.0063 (6)	0.0034 (6)	−0.0007 (5)
O2	0.0328 (7)	0.0281 (6)	0.0320 (6)	−0.0028 (6)	0.0018 (5)	0.0004 (5)
O3	0.0608 (10)	0.0875 (12)	0.0377 (8)	0.0235 (10)	0.0204 (8)	0.0163 (8)
O4	0.0346 (7)	0.0388 (7)	0.0394 (7)	0.0047 (7)	0.0011 (6)	0.0017 (6)
N1	0.0342 (8)	0.0273 (7)	0.0237 (7)	−0.0040 (7)	0.0002 (7)	0.0021 (6)
C9	0.0320 (9)	0.0370 (9)	0.0213 (8)	−0.0021 (8)	−0.0069 (7)	−0.0038 (7)
C4	0.0265 (8)	0.0242 (8)	0.0293 (8)	0.0021 (7)	0.0030 (8)	−0.0002 (7)
C5	0.0244 (8)	0.0259 (8)	0.0276 (8)	0.0056 (8)	0.0002 (7)	0.0008 (7)
C3	0.0358 (9)	0.0281 (9)	0.0299 (9)	0.0010 (8)	−0.0003 (7)	−0.0021 (7)
C1	0.0440 (11)	0.0412 (10)	0.0262 (9)	−0.0047 (10)	0.0091 (9)	0.0028 (8)
C7	0.0330 (10)	0.0429 (11)	0.0329 (9)	−0.0012 (9)	0.0014 (8)	0.0012 (8)
C2	0.0457 (11)	0.0394 (10)	0.0244 (8)	0.0017 (10)	0.0041 (8)	−0.0008 (8)
C14	0.0336 (10)	0.0353 (9)	0.0381 (10)	−0.0045 (9)	−0.0034 (8)	−0.0051 (8)
C8	0.0401 (10)	0.0342 (10)	0.0261 (8)	0.0035 (9)	−0.0044 (8)	−0.0047 (8)
C6	0.0348 (10)	0.0306 (9)	0.0234 (8)	−0.0009 (8)	0.0008 (7)	0.0016 (7)
C11	0.0358 (11)	0.0821 (18)	0.0348 (10)	−0.0077 (13)	0.0019 (9)	−0.0071 (11)
C10	0.0438 (11)	0.0510 (12)	0.0288 (9)	−0.0079 (11)	−0.0044 (9)	0.0044 (9)
C13	0.0497 (12)	0.0393 (11)	0.0571 (13)	0.0083 (10)	−0.0129 (12)	−0.0157 (10)
C15	0.0374 (11)	0.0488 (12)	0.0622 (14)	0.0082 (11)	0.0041 (11)	−0.0068 (11)
C12	0.0331 (11)	0.0811 (17)	0.0471 (12)	0.0114 (13)	−0.0041 (10)	−0.0286 (12)

Geometric parameters (Å, º) top

O1—C4	1.370 (2)	C7—C6	1.523 (3)
O1—C1	1.372 (2)	C2—H2	0.9500
O2—C5	1.237 (2)	C14—C13	1.384 (3)
O3—C7	1.198 (2)	C14—H14	0.9500
O4—C7	1.328 (2)	C8—C6	1.537 (2)
O4—C15	1.445 (2)	C8—H8A	0.9900
N1—C5	1.335 (2)	C8—H8B	0.9900
N1—C6	1.450 (2)	C6—H6	1.0000
N1—H1	0.8800	C11—C12	1.370 (4)
C9—C10	1.386 (3)	C11—C10	1.379 (3)
C9—C14	1.391 (3)	C11—H11	0.9500
C9—C8	1.502 (3)	C10—H10	0.9500
C4—C3	1.343 (2)	C13—C12	1.391 (3)
C4—C5	1.477 (2)	C13—H13	0.9500
C3—C2	1.421 (3)	C15—H15A	0.9800
C3—H3	0.9500	C15—H15B	0.9800
C1—C2	1.342 (3)	C15—H15C	0.9800
C1—H1A	0.9500	C12—H12	0.9500

C4—O1—C1	105.77 (14)	C9—C8—H8A	108.7
C7—O4—C15	115.13 (16)	C6—C8—H8A	108.7
C5—N1—C6	121.95 (15)	C9—C8—H8B	108.7
C5—N1—H1	119.0	C6—C8—H8B	108.7
C6—N1—H1	119.0	H8A—C8—H8B	107.6
C10—C9—C14	118.51 (18)	N1—C6—C7	114.34 (15)
C10—C9—C8	120.97 (17)	N1—C6—C8	110.71 (14)
C14—C9—C8	120.46 (17)	C7—C6—C8	107.68 (14)
C3—C4—O1	110.66 (15)	N1—C6—H6	108.0
C3—C4—C5	131.75 (16)	C7—C6—H6	108.0
O1—C4—C5	117.58 (14)	C8—C6—H6	108.0
O2—C5—N1	124.07 (15)	C12—C11—C10	120.0 (2)
O2—C5—C4	119.76 (15)	C12—C11—H11	120.0
N1—C5—C4	116.17 (15)	C10—C11—H11	120.0
C4—C3—C2	106.43 (16)	C11—C10—C9	121.2 (2)
C4—C3—H3	126.8	C11—C10—H10	119.4
C2—C3—H3	126.8	C9—C10—H10	119.4
C2—C1—O1	110.44 (17)	C14—C13—C12	120.0 (2)
C2—C1—H1A	124.8	C14—C13—H13	120.0
O1—C1—H1A	124.8	C12—C13—H13	120.0
O3—C7—O4	124.24 (19)	O4—C15—H15A	109.5
O3—C7—C6	122.07 (18)	O4—C15—H15B	109.5
O4—C7—C6	113.65 (15)	H15A—C15—H15B	109.5
C1—C2—C3	106.70 (16)	O4—C15—H15C	109.5
C1—C2—H2	126.6	H15A—C15—H15C	109.5
C3—C2—H2	126.6	H15B—C15—H15C	109.5
C13—C14—C9	120.4 (2)	C11—C12—C13	119.9 (2)
C13—C14—H14	119.8	C11—C12—H12	120.1
C9—C14—H14	119.8	C13—C12—H12	120.1
C9—C8—C6	114.20 (14)

C1—O1—C4—C3	0.1 (2)	C10—C9—C8—C6	104.93 (19)
C1—O1—C4—C5	−178.91 (15)	C14—C9—C8—C6	−77.8 (2)
C6—N1—C5—O2	3.2 (3)	C5—N1—C6—C7	−101.0 (2)
C6—N1—C5—C4	−176.91 (15)	C5—N1—C6—C8	137.22 (17)
C3—C4—C5—O2	10.9 (3)	O3—C7—C6—N1	174.0 (2)
O1—C4—C5—O2	−170.38 (14)	O4—C7—C6—N1	−8.1 (2)
C3—C4—C5—N1	−169.06 (19)	O3—C7—C6—C8	−62.6 (2)
O1—C4—C5—N1	9.7 (2)	O4—C7—C6—C8	115.41 (17)
O1—C4—C3—C2	−0.3 (2)	C9—C8—C6—N1	−59.7 (2)
C5—C4—C3—C2	178.49 (18)	C9—C8—C6—C7	174.61 (15)
C4—O1—C1—C2	0.2 (2)	C12—C11—C10—C9	0.4 (3)
C15—O4—C7—O3	2.4 (3)	C14—C9—C10—C11	−1.7 (3)
C15—O4—C7—C6	−175.53 (16)	C8—C9—C10—C11	175.65 (17)
O1—C1—C2—C3	−0.4 (2)	C9—C14—C13—C12	0.4 (3)
C4—C3—C2—C1	0.4 (2)	C10—C11—C12—C13	1.4 (3)
C10—C9—C14—C13	1.3 (3)	C14—C13—C12—C11	−1.8 (3)
C8—C9—C14—C13	−176.07 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.88	2.12	2.930 (2)	154

Symmetry code: (i) −x, y+1/2, −z+1/2.

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(S)-Methyl 2-[(furan-2-carbon­yl)amino]-3-phenyl­propanoate

Supporting information

Key indicators

checkCIF/PLATON results

(S)-Methyl 2-[(furan-2-carbonyl)amino]-3-phenylpropanoate