Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807055365/dn2262sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807055365/dn2262Isup2.hkl |
CCDC reference: 672984
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.004 Å
- R factor = 0.031
- wR factor = 0.072
- Data-to-parameter ratio = 8.2
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.80 mm PLAT230_ALERT_2_C Hirshfeld Test Diff for N1 - C8 .. 6.65 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C3 - C4 .. 5.55 su
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 1705 Count of symmetry unique reflns 1744 Completeness (_total/calc) 97.76% 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 PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11 = . S PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Vidyasagar Reddy et al. (2000); Lin et al. (2007); Dorow & Gingrich (1999).
The N-Benzoxycarbonyl-L-phenylalanine (2.99 g, 1 mmol), paraformaldehyde (0.6 g, 2 mmol) and 4-methylbenzenesulfonic acid (0.15 g, 0.6 mmol) were dissolved in benzene (150 ml). The solution was refluxed for 1 h with a Dean-Stark trap. After cooling to room temperature, the mixture was washed with 0.3 M aqueous K2CO3 solution, water, and saturated aqueous NaCl solution, then dried over Mg2SO4 (Vidyasagar et al., 2000). We got white soild after evaporation of the solvent. Single crystals were obtained by recrystallization from ethanol.
All H atoms were fixed geometrically and treated as riding with C—H = 0.93 Å (aromatic), 0.97 Å (methylene) or 0.98 Å (methine) with Uiso(H) = 1.2Ueq(C).
In the absence of significant anomalous scattering, the absolute configuration could not be reliably determined and then the Friedel pairs were merged and any references to the Flack parameter were removed. The absolute configuration was deduced from the synthetic procedure.
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
C18H17NO4 | F(000) = 328 |
Mr = 311.33 | Dx = 1.282 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 2497 reflections |
a = 11.4729 (11) Å | θ = 4.2–32.7° |
b = 5.9019 (4) Å | µ = 0.09 mm−1 |
c = 12.5093 (10) Å | T = 173 K |
β = 107.81 (1)° | Block, colorless |
V = 806.44 (11) Å3 | 0.80 × 0.37 × 0.23 mm |
Z = 2 |
Bruker APEX area-detector diffractometer | 1705 independent reflections |
Radiation source: fine-focus sealed tube | 1240 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
ϕ and ω scan | θmax = 26.0°, θmin = 4.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −14→13 |
Tmin = 0.934, Tmax = 0.981 | k = −7→7 |
5708 measured reflections | l = −15→13 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.072 | H-atom parameters constrained |
S = 0.95 | w = 1/[σ2(Fo2) + (0.0454P)2] where P = (Fo2 + 2Fc2)/3 |
1705 reflections | (Δ/σ)max < 0.001 |
208 parameters | Δρmax = 0.11 e Å−3 |
1 restraint | Δρmin = −0.15 e Å−3 |
C18H17NO4 | V = 806.44 (11) Å3 |
Mr = 311.33 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 11.4729 (11) Å | µ = 0.09 mm−1 |
b = 5.9019 (4) Å | T = 173 K |
c = 12.5093 (10) Å | 0.80 × 0.37 × 0.23 mm |
β = 107.81 (1)° |
Bruker APEX area-detector diffractometer | 1705 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 1240 reflections with I > 2σ(I) |
Tmin = 0.934, Tmax = 0.981 | Rint = 0.027 |
5708 measured reflections |
R[F2 > 2σ(F2)] = 0.031 | 1 restraint |
wR(F2) = 0.072 | H-atom parameters constrained |
S = 0.95 | Δρmax = 0.11 e Å−3 |
1705 reflections | Δρmin = −0.15 e Å−3 |
208 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 | ||
N1 | 0.42377 (15) | 0.7609 (3) | 0.84565 (14) | 0.0362 (4) | |
C8 | 0.36781 (19) | 0.8526 (4) | 0.91468 (16) | 0.0400 (5) | |
O1 | 0.28778 (13) | 0.7072 (2) | 0.93711 (12) | 0.0457 (4) | |
O3 | 0.58323 (14) | 0.7171 (3) | 0.77604 (14) | 0.0522 (4) | |
C11 | 0.41290 (18) | 0.5305 (4) | 0.80224 (17) | 0.0380 (5) | |
H11 | 0.4233 | 0.4231 | 0.8642 | 0.046* | |
O2 | 0.38833 (15) | 1.0438 (3) | 0.95256 (13) | 0.0540 (4) | |
C1 | 0.08937 (19) | 0.8764 (4) | 0.91329 (16) | 0.0391 (5) | |
O4 | 0.55782 (18) | 0.3612 (3) | 0.71837 (16) | 0.0665 (5) | |
C7 | 0.2070 (2) | 0.8026 (5) | 0.99621 (18) | 0.0520 (6) | |
H7A | 0.2465 | 0.9312 | 1.0411 | 0.062* | |
H7B | 0.1908 | 0.6897 | 1.0462 | 0.062* | |
C13 | 0.25038 (19) | 0.6702 (4) | 0.62687 (17) | 0.0412 (5) | |
C6 | 0.0774 (2) | 1.0868 (4) | 0.86208 (19) | 0.0470 (6) | |
H6 | 0.1430 | 1.1873 | 0.8806 | 0.056* | |
C18 | 0.1527 (2) | 0.8044 (4) | 0.63085 (17) | 0.0473 (6) | |
H18 | 0.1126 | 0.7714 | 0.6834 | 0.057* | |
C12 | 0.2927 (2) | 0.4786 (4) | 0.70912 (18) | 0.0443 (6) | |
H12A | 0.3042 | 0.3443 | 0.6687 | 0.053* | |
H12B | 0.2294 | 0.4455 | 0.7434 | 0.053* | |
C10 | 0.5233 (2) | 0.5193 (4) | 0.7604 (2) | 0.0464 (6) | |
C2 | −0.0100 (2) | 0.7305 (4) | 0.88517 (19) | 0.0478 (6) | |
H2 | −0.0031 | 0.5892 | 0.9195 | 0.057* | |
C9 | 0.5257 (2) | 0.8793 (4) | 0.8266 (2) | 0.0531 (6) | |
H9A | 0.4975 | 1.0078 | 0.7771 | 0.064* | |
H9B | 0.5818 | 0.9328 | 0.8969 | 0.064* | |
C3 | −0.1181 (2) | 0.7913 (5) | 0.8076 (2) | 0.0592 (7) | |
H3 | −0.1839 | 0.6913 | 0.7892 | 0.071* | |
C15 | 0.2702 (3) | 0.9083 (5) | 0.4770 (2) | 0.0657 (8) | |
H15 | 0.3108 | 0.9443 | 0.4253 | 0.079* | |
C17 | 0.1129 (2) | 0.9859 (4) | 0.5590 (2) | 0.0549 (7) | |
H17 | 0.0462 | 1.0717 | 0.5624 | 0.066* | |
C5 | −0.0318 (3) | 1.1480 (5) | 0.7835 (2) | 0.0578 (7) | |
H5 | −0.0392 | 1.2887 | 0.7485 | 0.069* | |
C14 | 0.3083 (2) | 0.7238 (5) | 0.54794 (18) | 0.0553 (6) | |
H14 | 0.3734 | 0.6355 | 0.5424 | 0.066* | |
C16 | 0.1727 (3) | 1.0383 (5) | 0.48261 (19) | 0.0614 (7) | |
H16 | 0.1475 | 1.1614 | 0.4347 | 0.074* | |
C4 | −0.1294 (3) | 1.0006 (5) | 0.7571 (2) | 0.0638 (8) | |
H4 | −0.2031 | 1.0425 | 0.7049 | 0.077* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0350 (9) | 0.0346 (10) | 0.0357 (9) | −0.0039 (8) | 0.0061 (8) | −0.0009 (8) |
C8 | 0.0378 (12) | 0.0417 (13) | 0.0317 (10) | 0.0002 (11) | −0.0022 (9) | 0.0031 (11) |
O1 | 0.0428 (9) | 0.0458 (9) | 0.0495 (9) | 0.0026 (8) | 0.0155 (7) | 0.0040 (7) |
O3 | 0.0434 (8) | 0.0498 (9) | 0.0658 (10) | −0.0059 (9) | 0.0204 (8) | 0.0041 (8) |
C11 | 0.0405 (12) | 0.0315 (10) | 0.0411 (11) | −0.0006 (10) | 0.0112 (9) | 0.0035 (10) |
O2 | 0.0617 (10) | 0.0457 (10) | 0.0511 (9) | −0.0065 (9) | 0.0121 (8) | −0.0122 (8) |
C1 | 0.0453 (13) | 0.0426 (12) | 0.0345 (11) | 0.0021 (11) | 0.0196 (10) | −0.0027 (10) |
O4 | 0.0763 (12) | 0.0482 (10) | 0.0890 (13) | 0.0123 (10) | 0.0463 (10) | 0.0088 (10) |
C7 | 0.0531 (14) | 0.0663 (16) | 0.0383 (12) | 0.0082 (13) | 0.0166 (11) | 0.0061 (11) |
C13 | 0.0399 (12) | 0.0472 (13) | 0.0312 (11) | −0.0092 (11) | 0.0031 (9) | −0.0082 (9) |
C6 | 0.0587 (16) | 0.0400 (14) | 0.0451 (13) | −0.0027 (12) | 0.0203 (12) | −0.0026 (10) |
C18 | 0.0464 (13) | 0.0572 (14) | 0.0349 (12) | −0.0048 (12) | 0.0074 (10) | −0.0004 (11) |
C12 | 0.0445 (12) | 0.0399 (12) | 0.0446 (13) | −0.0095 (10) | 0.0079 (11) | −0.0039 (10) |
C10 | 0.0467 (13) | 0.0422 (14) | 0.0495 (13) | 0.0045 (12) | 0.0135 (11) | 0.0095 (12) |
C2 | 0.0564 (14) | 0.0467 (13) | 0.0487 (13) | −0.0005 (13) | 0.0285 (12) | −0.0025 (11) |
C9 | 0.0518 (14) | 0.0463 (13) | 0.0630 (15) | −0.0135 (12) | 0.0201 (12) | −0.0061 (12) |
C3 | 0.0484 (15) | 0.0724 (18) | 0.0593 (15) | −0.0075 (13) | 0.0202 (13) | −0.0162 (14) |
C15 | 0.0684 (18) | 0.092 (2) | 0.0355 (13) | −0.0063 (17) | 0.0144 (13) | 0.0131 (14) |
C17 | 0.0622 (16) | 0.0579 (16) | 0.0403 (13) | 0.0052 (13) | 0.0094 (12) | −0.0033 (12) |
C5 | 0.0779 (18) | 0.0519 (14) | 0.0428 (13) | 0.0208 (15) | 0.0174 (14) | 0.0012 (11) |
C14 | 0.0496 (13) | 0.0779 (17) | 0.0374 (13) | 0.0003 (14) | 0.0117 (11) | −0.0026 (13) |
C16 | 0.0737 (18) | 0.0630 (16) | 0.0371 (13) | −0.0034 (16) | 0.0017 (13) | 0.0046 (12) |
C4 | 0.0502 (16) | 0.088 (2) | 0.0465 (14) | 0.0222 (17) | 0.0043 (12) | −0.0156 (16) |
N1—C8 | 1.338 (3) | C6—H6 | 0.9300 |
N1—C9 | 1.444 (3) | C18—C17 | 1.383 (3) |
N1—C11 | 1.455 (3) | C18—H18 | 0.9300 |
C8—O2 | 1.218 (3) | C12—H12A | 0.9700 |
C8—O1 | 1.348 (3) | C12—H12B | 0.9700 |
O1—C7 | 1.464 (3) | C2—C3 | 1.368 (4) |
O3—C10 | 1.339 (3) | C2—H2 | 0.9300 |
O3—C9 | 1.416 (3) | C9—H9A | 0.9700 |
C11—C10 | 1.512 (3) | C9—H9B | 0.9700 |
C11—C12 | 1.539 (3) | C3—C4 | 1.376 (4) |
C11—H11 | 0.9800 | C3—H3 | 0.9300 |
C1—C6 | 1.385 (3) | C15—C16 | 1.375 (4) |
C1—C2 | 1.386 (3) | C15—C14 | 1.388 (4) |
C1—C7 | 1.493 (3) | C15—H15 | 0.9300 |
O4—C10 | 1.197 (3) | C17—C16 | 1.371 (4) |
C7—H7A | 0.9700 | C17—H17 | 0.9300 |
C7—H7B | 0.9700 | C5—C4 | 1.376 (4) |
C13—C14 | 1.385 (3) | C5—H5 | 0.9300 |
C13—C18 | 1.386 (3) | C14—H14 | 0.9300 |
C13—C12 | 1.506 (3) | C16—H16 | 0.9300 |
C6—C5 | 1.383 (4) | C4—H4 | 0.9300 |
C8—N1—C9 | 118.93 (18) | C11—C12—H12B | 108.9 |
C8—N1—C11 | 128.01 (17) | H12A—C12—H12B | 107.7 |
C9—N1—C11 | 111.83 (18) | O4—C10—O3 | 121.3 (2) |
O2—C8—N1 | 123.5 (2) | O4—C10—C11 | 127.7 (2) |
O2—C8—O1 | 124.9 (2) | O3—C10—C11 | 111.0 (2) |
N1—C8—O1 | 111.62 (18) | C3—C2—C1 | 120.9 (2) |
C8—O1—C7 | 115.91 (17) | C3—C2—H2 | 119.5 |
C10—O3—C9 | 111.44 (18) | C1—C2—H2 | 119.5 |
N1—C11—C10 | 100.64 (17) | O3—C9—N1 | 104.96 (18) |
N1—C11—C12 | 115.04 (18) | O3—C9—H9A | 110.8 |
C10—C11—C12 | 112.36 (18) | N1—C9—H9A | 110.8 |
N1—C11—H11 | 109.5 | O3—C9—H9B | 110.8 |
C10—C11—H11 | 109.5 | N1—C9—H9B | 110.8 |
C12—C11—H11 | 109.5 | H9A—C9—H9B | 108.8 |
C6—C1—C2 | 118.8 (2) | C2—C3—C4 | 119.9 (3) |
C6—C1—C7 | 121.6 (2) | C2—C3—H3 | 120.1 |
C2—C1—C7 | 119.6 (2) | C4—C3—H3 | 120.1 |
O1—C7—C1 | 109.80 (16) | C16—C15—C14 | 120.4 (2) |
O1—C7—H7A | 109.7 | C16—C15—H15 | 119.8 |
C1—C7—H7A | 109.7 | C14—C15—H15 | 119.8 |
O1—C7—H7B | 109.7 | C16—C17—C18 | 119.5 (3) |
C1—C7—H7B | 109.7 | C16—C17—H17 | 120.3 |
H7A—C7—H7B | 108.2 | C18—C17—H17 | 120.3 |
C14—C13—C18 | 117.7 (2) | C4—C5—C6 | 119.9 (3) |
C14—C13—C12 | 122.3 (2) | C4—C5—H5 | 120.0 |
C18—C13—C12 | 120.0 (2) | C6—C5—H5 | 120.0 |
C5—C6—C1 | 120.2 (2) | C13—C14—C15 | 120.6 (2) |
C5—C6—H6 | 119.9 | C13—C14—H14 | 119.7 |
C1—C6—H6 | 119.9 | C15—C14—H14 | 119.7 |
C17—C18—C13 | 121.9 (2) | C17—C16—C15 | 119.9 (2) |
C17—C18—H18 | 119.0 | C17—C16—H16 | 120.1 |
C13—C18—H18 | 119.0 | C15—C16—H16 | 120.1 |
C13—C12—C11 | 113.25 (17) | C3—C4—C5 | 120.2 (2) |
C13—C12—H12A | 108.9 | C3—C4—H4 | 119.9 |
C11—C12—H12A | 108.9 | C5—C4—H4 | 119.9 |
C13—C12—H12B | 108.9 |
Experimental details
Crystal data | |
Chemical formula | C18H17NO4 |
Mr | 311.33 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 173 |
a, b, c (Å) | 11.4729 (11), 5.9019 (4), 12.5093 (10) |
β (°) | 107.81 (1) |
V (Å3) | 806.44 (11) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.80 × 0.37 × 0.23 |
Data collection | |
Diffractometer | Bruker APEX area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.934, 0.981 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5708, 1705, 1240 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.031, 0.072, 0.95 |
No. of reflections | 1705 |
No. of parameters | 208 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.11, −0.15 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996); ORTEP-3 for Windows (Farrugia, 1997).
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The title compound (I), has been used to synthesize dipeptides and N-methyl-α-amino acid (Dorow & Gingrich, 1999). The absolute configuration of the stereocentre remains unchanged during the synthetic procedure.
The title compound, C18H17N1O4, is built up from an oxazolidine-3-carboxylate moiety attached to two benzyl rings. The carboxylate and the oxazolidine are roughly coplanar with the largest deviation from the least-square plane being -0.144 (2) Å at the nitrogen atom. The two benzyl rings are located on the same side of this plane and make dihedral angle with it of 75.23 (4)° and 56.97 (7)° respectively (Fig. 1). The bond lengths and angles in (I) are in agreement with the values reported in the literature (Lin et al., 2007).