Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807036410/bx2093sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807036410/bx2093Isup2.hkl |
CCDC reference: 657872
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.005 Å
- R factor = 0.049
- wR factor = 0.134
- Data-to-parameter ratio = 10.1
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT725_ALERT_1_A D-H Calc 0.88000, Rep 0.83000 Dev... 0.05 Ang. N2 -H2 1.555 1.555 PLAT726_ALERT_1_A H...A Calc 2.36000, Rep 2.42000 Dev... 0.06 Ang. H2 -O5 1.555 1.555
Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C14 - C15 .. 14.11 su
Alert level C DIFMX01_ALERT_2_C The maximum difference density is > 0.1*ZMAX*0.75 _refine_diff_density_max given = 0.672 Test value = 0.600 DIFMX02_ALERT_1_C The maximum difference density is > 0.1*ZMAX*0.75 The relevant atom site should be identified. PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 3.20 PLAT097_ALERT_2_C Maximum (Positive) Residual Density ............ 0.67 e/A PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.59 Ratio PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.74 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.11 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.43 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for O5 - C13 .. 5.71 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C14 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C22 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5 PLAT728_ALERT_1_C D-H..A Calc 107.00, Rep 105.00 Dev... 2.00 Deg. N2 -H2 -O5 1.555 1.555 1.555
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 27.05 From the CIF: _reflns_number_total 3189 Count of symmetry unique reflns 3208 Completeness (_total/calc) 99.41% 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 PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C18 = . S PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 3
2 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 16 ALERT level C = Check and explain 5 ALERT level G = General alerts; check 8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 10 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: El-Naggar et al. (1976); Gomis-Ruth et al. (1998); Wipf & Halter (2005); Zeng & Liu (2005).
The synthesis of (I) was reported by El-Naggar et al.,1976. A solution of Furan-2-carbonyl chloride (0.66 g, 5 mmol) in dichloromethane (2.5 ml) was added dropwise, under stirring, to L-leucine methyl ester (0.91 g, 5 mmol) in dichloromethane (5 ml). The mixture was stirred at room temperature for 2 h and then poured into water. After filtration, the solution was wash with water(5 ml), The organic phase was dried over Na2SO4 and evaporated under reduced pressure. The residue was dissolved in ethanol at room temperature. Colorless orthorhombic crystals suitable for X-ray analysis (m.p. 362 K, 81.6 percent yield) grew over a period of one week when the solution was exposed to air.
Hydrogen atoms attached to C or N atoms were located at geometrically calculated positions [0.95 (CH), 0.99 (CH2), 0.98 (CH3), 0.88 (NH)] and refined with isotropic thermal parameters Uiso(H) equal to 1.2 for CH2, CH, and NH, 1.5 for CH3 Ueq(C atoms). The highest positive and negative electron-density residuals are located 0.93 and 0.84Å from C14 and C23 respectively.
Furan derivatives are well known in many organisms (Wipf et al., 2005), and some of them are bioactive substances (Gomis-Ruth et al., 1998). In our search for bioactive compounds, a series of furan(2-carbonyl)amino acid esters, including the title compound, (I), have been synthesized by the reaction of amino acid esters with Furan-2-carbonyl chloride. We report here its crystal structure. Bond lengths and angles are unexceptional and are in good agreement with the corresponding values in (S)-Methyl 4-methyl-2-(1H-pyrrole-2-carboxamido)-pentanoate (Zeng & Liu, 2005) and 1-(4-methoxyphenyl)-3-(3-methyl-2-furan-carbonyl)-thiourea (Hritzova et al., 2005). There are two molecules in the asymmetric unit (Fig. 1) and only one kind of intermolecular hydrogen bonds in the crystal structure. Every molecule is connected with two other molecules by hydrogen-bond interactions, generating extended chains along the c axis, Figure 2.
For related literature, see: El-Naggar et al. (1976); Gomis-Ruth et al. (1998); Wipf & Halter (2005); Zeng & Liu (2005).
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); 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.
C12H17NO4 | Dx = 1.230 Mg m−3 |
Mr = 239.27 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 13310 reflections |
a = 8.7674 (10) Å | θ = 12–18° |
b = 16.1703 (18) Å | µ = 0.09 mm−1 |
c = 18.224 (2) Å | T = 173 K |
V = 2583.6 (5) Å3 | Block, colourless |
Z = 8 | 0.50 × 0.40 × 0.20 mm |
F(000) = 1024 |
Bruker SMART 1000 CCD aea-detector diffractometer | 3189 independent reflections |
Radiation source: fine-focus sealed tube | 2685 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
ω scans | θmax = 27.1°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→11 |
Tmin = 0.957, Tmax = 0.982 | k = −13→20 |
13310 measured reflections | l = −23→22 |
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)] = 0.049 | H-atom parameters constrained |
wR(F2) = 0.134 | w = 1/[σ2(Fo2) + (0.0652P)2 + 1.1602P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
3189 reflections | Δρmax = 0.67 e Å−3 |
315 parameters | Δρmin = −0.21 e Å−3 |
3 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0046 (9) |
C12H17NO4 | V = 2583.6 (5) Å3 |
Mr = 239.27 | Z = 8 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 8.7674 (10) Å | µ = 0.09 mm−1 |
b = 16.1703 (18) Å | T = 173 K |
c = 18.224 (2) Å | 0.50 × 0.40 × 0.20 mm |
Bruker SMART 1000 CCD aea-detector diffractometer | 3189 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2685 reflections with I > 2σ(I) |
Tmin = 0.957, Tmax = 0.982 | Rint = 0.024 |
13310 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 3 restraints |
wR(F2) = 0.134 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.67 e Å−3 |
3189 reflections | Δρmin = −0.21 e Å−3 |
315 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.1237 (3) | 0.61581 (14) | 0.45097 (12) | 0.0445 (5) | |
O2 | 0.4018 (3) | 0.58090 (14) | 0.58910 (11) | 0.0404 (5) | |
O3 | 0.6183 (3) | 0.55287 (14) | 0.44903 (13) | 0.0461 (6) | |
O4 | 0.7289 (3) | 0.45796 (17) | 0.52091 (19) | 0.0665 (9) | |
O5 | 0.2261 (3) | 0.46393 (17) | 0.69428 (15) | 0.0632 (8) | |
O6 | 0.3297 (3) | 0.56474 (14) | 0.86200 (11) | 0.0434 (5) | |
O7 | 0.2604 (3) | 0.74834 (16) | 0.72373 (15) | 0.0574 (7) | |
O8 | 0.4538 (3) | 0.81196 (13) | 0.78045 (15) | 0.0531 (7) | |
N1 | 0.3328 (3) | 0.49843 (15) | 0.49519 (14) | 0.0319 (5) | |
H1 | 0.2638 | 0.4855 | 0.4621 | 0.038* | |
N2 | 0.3946 (3) | 0.59578 (14) | 0.74474 (13) | 0.0328 (5) | |
H2 | 0.3900 | 0.5799 | 0.6986 | 0.039* | |
C1 | 0.2009 (3) | 0.62688 (18) | 0.51507 (16) | 0.0336 (6) | |
C2 | 0.1566 (4) | 0.6981 (2) | 0.5477 (2) | 0.0490 (8) | |
H2A | 0.1927 | 0.7201 | 0.5928 | 0.059* | |
C3 | 0.0452 (5) | 0.7331 (2) | 0.5007 (3) | 0.0592 (10) | |
H3 | −0.0078 | 0.7837 | 0.5080 | 0.071* | |
C4 | 0.0290 (5) | 0.6822 (2) | 0.4449 (2) | 0.0573 (10) | |
H4 | −0.0400 | 0.6907 | 0.4054 | 0.069* | |
C5 | 0.3179 (3) | 0.56685 (18) | 0.53628 (14) | 0.0305 (6) | |
C6 | 0.4648 (3) | 0.44653 (18) | 0.50666 (16) | 0.0332 (6) | |
H6 | 0.4681 | 0.4293 | 0.5593 | 0.040* | |
C7 | 0.6099 (4) | 0.49425 (19) | 0.48859 (18) | 0.0382 (7) | |
C8 | 0.8780 (5) | 0.4917 (3) | 0.5032 (3) | 0.0790 (15) | |
H8A | 0.8984 | 0.4840 | 0.4508 | 0.118* | |
H8B | 0.9563 | 0.4630 | 0.5319 | 0.118* | |
H8C | 0.8799 | 0.5508 | 0.5149 | 0.118* | |
C9 | 0.4580 (3) | 0.36901 (17) | 0.45842 (17) | 0.0345 (6) | |
H9A | 0.4396 | 0.3865 | 0.4071 | 0.041* | |
H9B | 0.5590 | 0.3417 | 0.4599 | 0.041* | |
C10 | 0.3368 (4) | 0.30551 (18) | 0.47946 (16) | 0.0359 (7) | |
H10 | 0.2353 | 0.3337 | 0.4812 | 0.043* | |
C11 | 0.3688 (5) | 0.2675 (2) | 0.5542 (2) | 0.0537 (9) | |
H11A | 0.2890 | 0.2271 | 0.5660 | 0.081* | |
H11B | 0.3699 | 0.3110 | 0.5916 | 0.081* | |
H11C | 0.4681 | 0.2397 | 0.5532 | 0.081* | |
C12 | 0.3321 (5) | 0.2390 (2) | 0.4208 (2) | 0.0516 (9) | |
H12A | 0.3141 | 0.2645 | 0.3728 | 0.077* | |
H12B | 0.2495 | 0.2000 | 0.4317 | 0.077* | |
H12C | 0.4296 | 0.2093 | 0.4200 | 0.077* | |
C13 | 0.2279 (3) | 0.48155 (17) | 0.76822 (17) | 0.0346 (6) | |
C14 | 0.1322 (5) | 0.4294 (3) | 0.8043 (2) | 0.0664 (12) | |
H14 | 0.1096 | 0.4271 | 0.8552 | 0.080* | |
C15 | 0.0722 (4) | 0.3773 (2) | 0.7445 (3) | 0.0614 (11) | |
H15 | 0.0015 | 0.3333 | 0.7503 | 0.074* | |
C16 | 0.1313 (5) | 0.4012 (3) | 0.6822 (3) | 0.0745 (13) | |
H16 | 0.1100 | 0.3776 | 0.6356 | 0.089* | |
C17 | 0.3217 (3) | 0.55087 (17) | 0.79574 (15) | 0.0314 (6) | |
C18 | 0.4802 (3) | 0.66905 (16) | 0.76288 (15) | 0.0308 (6) | |
H18 | 0.5107 | 0.6656 | 0.8157 | 0.037* | |
C19 | 0.3825 (4) | 0.74590 (18) | 0.75269 (16) | 0.0362 (6) | |
C20 | 0.3752 (5) | 0.8901 (2) | 0.7729 (3) | 0.0628 (11) | |
H20A | 0.3565 | 0.9013 | 0.7208 | 0.094* | |
H20B | 0.4381 | 0.9344 | 0.7936 | 0.094* | |
H20C | 0.2777 | 0.8876 | 0.7991 | 0.094* | |
C21 | 0.6249 (4) | 0.67787 (17) | 0.71650 (17) | 0.0355 (6) | |
H21A | 0.5948 | 0.6845 | 0.6645 | 0.043* | |
H21B | 0.6784 | 0.7291 | 0.7315 | 0.043* | |
C22 | 0.7360 (4) | 0.60601 (19) | 0.72204 (19) | 0.0413 (7) | |
H22 | 0.6845 | 0.5562 | 0.7010 | 0.050* | |
C23 | 0.7791 (6) | 0.5861 (3) | 0.7997 (2) | 0.0776 (15) | |
H23A | 0.8320 | 0.6335 | 0.8215 | 0.116* | |
H23B | 0.8467 | 0.5378 | 0.8002 | 0.116* | |
H23C | 0.6869 | 0.5739 | 0.8281 | 0.116* | |
C24 | 0.8755 (5) | 0.6246 (3) | 0.6743 (3) | 0.0844 (16) | |
H24A | 0.8422 | 0.6378 | 0.6243 | 0.127* | |
H24B | 0.9424 | 0.5761 | 0.6732 | 0.127* | |
H24C | 0.9310 | 0.6718 | 0.6948 | 0.127* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0484 (13) | 0.0439 (12) | 0.0411 (12) | 0.0026 (11) | −0.0065 (11) | 0.0066 (10) |
O2 | 0.0405 (12) | 0.0506 (13) | 0.0300 (10) | 0.0006 (11) | −0.0022 (9) | −0.0072 (9) |
O3 | 0.0451 (13) | 0.0420 (12) | 0.0511 (13) | −0.0068 (11) | 0.0038 (11) | 0.0067 (11) |
O4 | 0.0329 (12) | 0.0489 (14) | 0.118 (2) | −0.0080 (12) | −0.0183 (15) | 0.0253 (16) |
O5 | 0.0635 (17) | 0.0629 (16) | 0.0634 (16) | −0.0149 (15) | −0.0060 (14) | −0.0204 (14) |
O6 | 0.0537 (13) | 0.0434 (12) | 0.0330 (11) | −0.0086 (11) | 0.0053 (10) | 0.0030 (10) |
O7 | 0.0539 (15) | 0.0556 (14) | 0.0627 (15) | 0.0180 (13) | −0.0205 (13) | −0.0142 (13) |
O8 | 0.0473 (14) | 0.0269 (11) | 0.0851 (18) | 0.0032 (10) | −0.0039 (13) | −0.0033 (11) |
N1 | 0.0307 (12) | 0.0323 (12) | 0.0326 (12) | 0.0003 (10) | −0.0055 (11) | −0.0018 (10) |
N2 | 0.0396 (13) | 0.0315 (12) | 0.0275 (11) | −0.0055 (11) | 0.0016 (11) | −0.0014 (9) |
C1 | 0.0308 (15) | 0.0336 (14) | 0.0364 (15) | −0.0043 (12) | 0.0052 (12) | 0.0009 (12) |
C2 | 0.0434 (18) | 0.0398 (17) | 0.064 (2) | −0.0004 (15) | 0.0038 (17) | −0.0098 (16) |
C3 | 0.050 (2) | 0.0391 (19) | 0.088 (3) | 0.0081 (16) | 0.001 (2) | 0.005 (2) |
C4 | 0.056 (2) | 0.052 (2) | 0.064 (2) | 0.0095 (19) | −0.009 (2) | 0.0203 (19) |
C5 | 0.0282 (13) | 0.0360 (14) | 0.0272 (13) | −0.0068 (12) | 0.0046 (11) | −0.0013 (11) |
C6 | 0.0302 (14) | 0.0325 (14) | 0.0370 (14) | −0.0032 (12) | −0.0031 (12) | 0.0015 (13) |
C7 | 0.0349 (15) | 0.0322 (15) | 0.0474 (18) | −0.0032 (13) | −0.0032 (15) | −0.0024 (13) |
C8 | 0.036 (2) | 0.067 (3) | 0.134 (4) | −0.012 (2) | −0.009 (3) | 0.008 (3) |
C9 | 0.0315 (14) | 0.0312 (14) | 0.0409 (16) | −0.0003 (12) | 0.0053 (13) | 0.0010 (13) |
C10 | 0.0330 (15) | 0.0303 (14) | 0.0443 (16) | −0.0028 (13) | 0.0009 (13) | 0.0020 (12) |
C11 | 0.056 (2) | 0.055 (2) | 0.0502 (19) | −0.0210 (19) | −0.0034 (18) | 0.0124 (17) |
C12 | 0.061 (2) | 0.0374 (17) | 0.056 (2) | −0.0111 (17) | 0.0045 (18) | −0.0041 (16) |
C13 | 0.0312 (14) | 0.0315 (14) | 0.0410 (16) | 0.0014 (12) | 0.0004 (13) | 0.0043 (12) |
C14 | 0.046 (2) | 0.070 (3) | 0.084 (3) | 0.0039 (19) | 0.006 (2) | 0.039 (2) |
C15 | 0.0416 (19) | 0.0365 (18) | 0.106 (3) | −0.0111 (16) | −0.013 (2) | −0.001 (2) |
C16 | 0.066 (3) | 0.062 (3) | 0.095 (3) | −0.019 (2) | −0.010 (3) | −0.020 (3) |
C17 | 0.0326 (14) | 0.0294 (13) | 0.0322 (14) | 0.0040 (12) | 0.0036 (12) | 0.0036 (12) |
C18 | 0.0375 (15) | 0.0261 (13) | 0.0288 (13) | −0.0025 (12) | −0.0011 (12) | 0.0007 (11) |
C19 | 0.0389 (15) | 0.0344 (15) | 0.0352 (14) | 0.0021 (13) | 0.0013 (14) | 0.0018 (12) |
C20 | 0.066 (3) | 0.0301 (16) | 0.092 (3) | 0.0137 (17) | 0.007 (2) | 0.0027 (18) |
C21 | 0.0403 (16) | 0.0269 (13) | 0.0394 (15) | −0.0041 (12) | 0.0001 (13) | −0.0010 (12) |
C22 | 0.0374 (16) | 0.0318 (14) | 0.0548 (19) | 0.0011 (13) | 0.0017 (15) | −0.0077 (14) |
C23 | 0.077 (3) | 0.083 (3) | 0.073 (3) | 0.045 (3) | −0.029 (2) | −0.012 (2) |
C24 | 0.059 (3) | 0.067 (3) | 0.127 (4) | 0.006 (2) | 0.041 (3) | −0.010 (3) |
O1—C1 | 1.362 (4) | C10—C12 | 1.517 (4) |
O1—C4 | 1.362 (4) | C10—C11 | 1.521 (4) |
O2—C5 | 1.233 (3) | C10—H10 | 1.0000 |
O3—C7 | 1.193 (4) | C11—H11A | 0.9800 |
O4—C7 | 1.335 (4) | C11—H11B | 0.9800 |
O4—C8 | 1.453 (5) | C11—H11C | 0.9800 |
O5—C16 | 1.329 (5) | C12—H12A | 0.9800 |
O5—C13 | 1.377 (4) | C12—H12B | 0.9800 |
O6—C17 | 1.230 (3) | C12—H12C | 0.9800 |
O7—C19 | 1.194 (4) | C13—C14 | 1.359 (5) |
O8—C19 | 1.337 (4) | C13—C17 | 1.478 (4) |
O8—C20 | 1.446 (4) | C14—C15 | 1.474 (5) |
N1—C5 | 1.342 (4) | C14—H14 | 0.9500 |
N1—C6 | 1.444 (4) | C15—C16 | 1.307 (6) |
N1—H1 | 0.8800 | C15—H15 | 0.9500 |
N2—C17 | 1.342 (4) | C16—H16 | 0.9500 |
N2—C18 | 1.441 (4) | C18—C19 | 1.520 (4) |
N2—H2 | 0.8800 | C18—C21 | 1.531 (4) |
C1—C2 | 1.353 (4) | C18—H18 | 1.0000 |
C1—C5 | 1.465 (4) | C20—H20A | 0.9800 |
C2—C3 | 1.417 (6) | C20—H20B | 0.9800 |
C2—H2A | 0.9500 | C20—H20C | 0.9800 |
C3—C4 | 1.315 (6) | C21—C22 | 1.520 (4) |
C3—H3 | 0.9500 | C21—H21A | 0.9900 |
C4—H4 | 0.9500 | C21—H21B | 0.9900 |
C6—C7 | 1.524 (4) | C22—C23 | 1.499 (5) |
C6—C9 | 1.532 (4) | C22—C24 | 1.530 (5) |
C6—H6 | 1.0000 | C22—H22 | 1.0000 |
C8—H8A | 0.9800 | C23—H23A | 0.9800 |
C8—H8B | 0.9800 | C23—H23B | 0.9800 |
C8—H8C | 0.9800 | C23—H23C | 0.9800 |
C9—C10 | 1.527 (4) | C24—H24A | 0.9800 |
C9—H9A | 0.9900 | C24—H24B | 0.9800 |
C9—H9B | 0.9900 | C24—H24C | 0.9800 |
C1—O1—C4 | 105.6 (3) | C10—C12—H12B | 109.5 |
C7—O4—C8 | 116.2 (3) | H12A—C12—H12B | 109.5 |
C16—O5—C13 | 109.1 (3) | C10—C12—H12C | 109.5 |
C19—O8—C20 | 116.1 (3) | H12A—C12—H12C | 109.5 |
C5—N1—C6 | 118.4 (2) | H12B—C12—H12C | 109.5 |
C5—N1—H1 | 120.8 | C14—C13—O5 | 109.7 (3) |
C6—N1—H1 | 120.8 | C14—C13—C17 | 130.5 (3) |
C17—N2—C18 | 122.3 (2) | O5—C13—C17 | 119.7 (3) |
C17—N2—H2 | 118.9 | C13—C14—C15 | 102.5 (3) |
C18—N2—H2 | 118.9 | C13—C14—H14 | 128.7 |
C2—C1—O1 | 110.3 (3) | C15—C14—H14 | 128.7 |
C2—C1—C5 | 130.5 (3) | C16—C15—C14 | 109.4 (3) |
O1—C1—C5 | 119.2 (3) | C16—C15—H15 | 125.3 |
C1—C2—C3 | 105.8 (3) | C14—C15—H15 | 125.3 |
C1—C2—H2A | 127.1 | C15—C16—O5 | 109.2 (4) |
C3—C2—H2A | 127.1 | C15—C16—H16 | 125.4 |
C4—C3—C2 | 107.0 (3) | O5—C16—H16 | 125.4 |
C4—C3—H3 | 126.5 | O6—C17—N2 | 123.6 (3) |
C2—C3—H3 | 126.5 | O6—C17—C13 | 120.2 (3) |
C3—C4—O1 | 111.4 (3) | N2—C17—C13 | 116.1 (2) |
C3—C4—H4 | 124.3 | N2—C18—C19 | 110.5 (2) |
O1—C4—H4 | 124.3 | N2—C18—C21 | 112.4 (2) |
O2—C5—N1 | 122.0 (3) | C19—C18—C21 | 108.8 (2) |
O2—C5—C1 | 120.1 (3) | N2—C18—H18 | 108.3 |
N1—C5—C1 | 117.9 (2) | C19—C18—H18 | 108.3 |
N1—C6—C7 | 110.1 (2) | C21—C18—H18 | 108.3 |
N1—C6—C9 | 111.2 (2) | O7—C19—O8 | 124.0 (3) |
C7—C6—C9 | 108.8 (2) | O7—C19—C18 | 125.9 (3) |
N1—C6—H6 | 108.9 | O8—C19—C18 | 110.1 (2) |
C7—C6—H6 | 108.9 | O8—C20—H20A | 109.5 |
C9—C6—H6 | 108.9 | O8—C20—H20B | 109.5 |
O3—C7—O4 | 124.6 (3) | H20A—C20—H20B | 109.5 |
O3—C7—C6 | 125.8 (3) | O8—C20—H20C | 109.5 |
O4—C7—C6 | 109.6 (2) | H20A—C20—H20C | 109.5 |
O4—C8—H8A | 109.5 | H20B—C20—H20C | 109.5 |
O4—C8—H8B | 109.5 | C22—C21—C18 | 115.0 (2) |
H8A—C8—H8B | 109.5 | C22—C21—H21A | 108.5 |
O4—C8—H8C | 109.5 | C18—C21—H21A | 108.5 |
H8A—C8—H8C | 109.5 | C22—C21—H21B | 108.5 |
H8B—C8—H8C | 109.5 | C18—C21—H21B | 108.5 |
C10—C9—C6 | 115.7 (2) | H21A—C21—H21B | 107.5 |
C10—C9—H9A | 108.4 | C23—C22—C21 | 112.9 (3) |
C6—C9—H9A | 108.4 | C23—C22—C24 | 112.2 (4) |
C10—C9—H9B | 108.4 | C21—C22—C24 | 108.9 (3) |
C6—C9—H9B | 108.4 | C23—C22—H22 | 107.6 |
H9A—C9—H9B | 107.4 | C21—C22—H22 | 107.6 |
C12—C10—C11 | 110.4 (3) | C24—C22—H22 | 107.6 |
C12—C10—C9 | 108.6 (3) | C22—C23—H23A | 109.5 |
C11—C10—C9 | 111.6 (3) | C22—C23—H23B | 109.5 |
C12—C10—H10 | 108.7 | H23A—C23—H23B | 109.5 |
C11—C10—H10 | 108.7 | C22—C23—H23C | 109.5 |
C9—C10—H10 | 108.7 | H23A—C23—H23C | 109.5 |
C10—C11—H11A | 109.5 | H23B—C23—H23C | 109.5 |
C10—C11—H11B | 109.5 | C22—C24—H24A | 109.5 |
H11A—C11—H11B | 109.5 | C22—C24—H24B | 109.5 |
C10—C11—H11C | 109.5 | H24A—C24—H24B | 109.5 |
H11A—C11—H11C | 109.5 | C22—C24—H24C | 109.5 |
H11B—C11—H11C | 109.5 | H24A—C24—H24C | 109.5 |
C10—C12—H12A | 109.5 | H24B—C24—H24C | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O6i | 0.88 | 2.16 | 2.994 (3) | 159 |
N2—H2···O2 | 0.88 | 2.00 | 2.847 (3) | 162 |
N2—H2···O5 | 0.83 | 2.42 | 2.751 (4) | 105 |
Symmetry code: (i) −x+1/2, −y+1, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C12H17NO4 |
Mr | 239.27 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 173 |
a, b, c (Å) | 8.7674 (10), 16.1703 (18), 18.224 (2) |
V (Å3) | 2583.6 (5) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.50 × 0.40 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART 1000 CCD aea-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.957, 0.982 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13310, 3189, 2685 |
Rint | 0.024 |
(sin θ/λ)max (Å−1) | 0.640 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.134, 1.05 |
No. of reflections | 3189 |
No. of parameters | 315 |
No. of restraints | 3 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.67, −0.21 |
Computer programs: SMART (Bruker, 1997), SMART, SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O6i | 0.88 | 2.16 | 2.994 (3) | 158.5 |
N2—H2···O2 | 0.88 | 2.00 | 2.847 (3) | 161.7 |
N2—H2···O5 | 0.83 | 2.42 | 2.751 (4) | 105 |
Symmetry code: (i) −x+1/2, −y+1, z−1/2. |
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Furan derivatives are well known in many organisms (Wipf et al., 2005), and some of them are bioactive substances (Gomis-Ruth et al., 1998). In our search for bioactive compounds, a series of furan(2-carbonyl)amino acid esters, including the title compound, (I), have been synthesized by the reaction of amino acid esters with Furan-2-carbonyl chloride. We report here its crystal structure. Bond lengths and angles are unexceptional and are in good agreement with the corresponding values in (S)-Methyl 4-methyl-2-(1H-pyrrole-2-carboxamido)-pentanoate (Zeng & Liu, 2005) and 1-(4-methoxyphenyl)-3-(3-methyl-2-furan-carbonyl)-thiourea (Hritzova et al., 2005). There are two molecules in the asymmetric unit (Fig. 1) and only one kind of intermolecular hydrogen bonds in the crystal structure. Every molecule is connected with two other molecules by hydrogen-bond interactions, generating extended chains along the c axis, Figure 2.