Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100001712/qb0164sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100001712/qb0164Isup2.hkl |
CCDC reference: 143333
N-acetyl-L-phenylalanine was obtained from Sigma Chemical Corporation (St Louis, Missouri). Crystals were grown from water and analyzed.
H atoms were allowed to refine isotropically. The range of C—H distances is 0.92 (2)–1.01 (2) Å; N—H = 0.86 (2) Å; O—H = 0.87 (2) Å.
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SHELXTL (Bruker, 1998); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; software used to prepare material for publication: SHELXTL.
C11H13NO3 | Dx = 1.285 Mg m−3 |
Mr = 207.22 | Melting point = 444–446 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
a = 5.6528 (1) Å | Cell parameters from 6900 reflections |
b = 11.1532 (2) Å | θ = 2.4–30.5° |
c = 16.9897 (1) Å | µ = 0.09 mm−1 |
V = 1071.15 (3) Å3 | T = 158 K |
Z = 4 | Needle, colourless |
F(000) = 440 | 0.54 × 0.14 × 0.12 mm |
CCD area-detector diffractometer | 1778 reflections with I > 2σ(I) |
Radiation source: sealed tube | Rint = 0.019 |
Graphite monochromator | θmax = 30.5°, θmin = 2.4° |
ω scans | h = −8→7 |
15627 measured reflections | k = −15→15 |
1866 independent reflections | l = −24→22 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.028 | All H-atom parameters refined |
wR(F2) = 0.077 | w = 1/[σ2(Fo2) + (0.0443P)2 + 0.1409P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
1866 reflections | Δρmax = 0.26 e Å−3 |
190 parameters | Δρmin = −0.18 e Å−3 |
0 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: 0.010 (3) |
C11H13NO3 | V = 1071.15 (3) Å3 |
Mr = 207.22 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 5.6528 (1) Å | µ = 0.09 mm−1 |
b = 11.1532 (2) Å | T = 158 K |
c = 16.9897 (1) Å | 0.54 × 0.14 × 0.12 mm |
CCD area-detector diffractometer | 1778 reflections with I > 2σ(I) |
15627 measured reflections | Rint = 0.019 |
1866 independent reflections |
R[F2 > 2σ(F2)] = 0.028 | 0 restraints |
wR(F2) = 0.077 | All H-atom parameters refined |
S = 1.08 | Δρmax = 0.26 e Å−3 |
1866 reflections | Δρmin = −0.18 e Å−3 |
190 parameters |
Experimental. A single-crystal was mounted on a teflon cryo-loop using a thin, inert oil. Diffraction data were collected at 158 (2) K on a Brüker Platform SMART-CCD diffractometer fitted with Mo radiation and a graphite monochromator. A full sphere of data was collected to a theta max. of 30.49 degrees. The space group was uniquely determined by analysis of the systematic absences. The configuration was assigned based on the known ciral center. Friedel opposites were merged for the light-atom, non-centrosymmetric structure. Data were processed via SADABS [Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany] with u*r equal zero. |
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 | 0.28171 (17) | 1.04065 (9) | 0.35019 (6) | 0.01924 (19) | |
H1 | 0.411 (4) | 1.0784 (17) | 0.3584 (10) | 0.033 (4)* | |
O1 | 0.07877 (16) | 0.92041 (9) | 0.26840 (5) | 0.0266 (2) | |
O2 | 0.07404 (17) | 1.25578 (9) | 0.32252 (6) | 0.0306 (2) | |
H2 | −0.013 (4) | 1.308 (2) | 0.2977 (13) | 0.053 (6)* | |
O3 | −0.27864 (17) | 1.18749 (9) | 0.36241 (7) | 0.0318 (2) | |
C1 | 0.4922 (2) | 0.94921 (13) | 0.24048 (8) | 0.0256 (3) | |
H1B | 0.508 (5) | 0.865 (2) | 0.2270 (13) | 0.057 (6)* | |
H1C | 0.628 (4) | 0.9705 (18) | 0.2670 (12) | 0.041 (5)* | |
H1D | 0.476 (4) | 0.9957 (18) | 0.1918 (12) | 0.049 (6)* | |
C2 | 0.2696 (2) | 0.96823 (10) | 0.28693 (6) | 0.0186 (2) | |
C3 | 0.0688 (2) | 1.07219 (10) | 0.39365 (6) | 0.0189 (2) | |
H3 | −0.043 (3) | 1.0033 (13) | 0.3907 (8) | 0.018 (4)* | |
C4 | −0.0645 (2) | 1.17777 (10) | 0.35682 (6) | 0.0201 (2) | |
C5 | 0.1275 (3) | 1.10111 (11) | 0.48030 (7) | 0.0237 (2) | |
H5A | 0.260 (4) | 1.1611 (16) | 0.4829 (11) | 0.035 (5)* | |
H5B | −0.012 (4) | 1.1380 (16) | 0.5021 (11) | 0.033 (5)* | |
C6 | 0.1905 (2) | 0.99041 (10) | 0.52759 (6) | 0.0212 (2) | |
C7 | 0.4023 (2) | 0.98254 (12) | 0.56921 (7) | 0.0277 (3) | |
H7 | 0.519 (4) | 1.0446 (18) | 0.5668 (11) | 0.041 (5)* | |
C8 | 0.4514 (3) | 0.88260 (15) | 0.61604 (8) | 0.0341 (3) | |
H8 | 0.593 (4) | 0.8773 (18) | 0.6437 (11) | 0.039 (5)* | |
C9 | 0.2903 (3) | 0.78902 (13) | 0.62067 (8) | 0.0344 (3) | |
H9 | 0.326 (4) | 0.7235 (19) | 0.6534 (12) | 0.049 (5)* | |
C10 | 0.0805 (3) | 0.79499 (12) | 0.57849 (8) | 0.0317 (3) | |
H10 | −0.034 (4) | 0.7316 (19) | 0.5787 (12) | 0.044 (5)* | |
C11 | 0.0306 (2) | 0.89513 (11) | 0.53248 (7) | 0.0249 (2) | |
H11 | −0.117 (3) | 0.9005 (16) | 0.5042 (11) | 0.032 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0171 (4) | 0.0193 (4) | 0.0214 (4) | −0.0020 (4) | −0.0004 (3) | −0.0014 (3) |
O1 | 0.0213 (4) | 0.0306 (4) | 0.0279 (4) | −0.0051 (4) | 0.0024 (3) | −0.0103 (4) |
O2 | 0.0212 (4) | 0.0308 (5) | 0.0399 (5) | 0.0027 (4) | 0.0030 (4) | 0.0180 (4) |
O3 | 0.0189 (4) | 0.0279 (5) | 0.0485 (6) | −0.0006 (4) | 0.0019 (4) | 0.0032 (4) |
C1 | 0.0187 (5) | 0.0319 (6) | 0.0264 (6) | 0.0019 (5) | 0.0022 (4) | −0.0034 (5) |
C2 | 0.0192 (5) | 0.0170 (4) | 0.0194 (4) | 0.0006 (4) | −0.0001 (4) | 0.0014 (4) |
C3 | 0.0204 (4) | 0.0171 (4) | 0.0191 (4) | −0.0011 (4) | 0.0015 (4) | −0.0004 (4) |
C4 | 0.0205 (5) | 0.0199 (5) | 0.0200 (4) | −0.0009 (4) | −0.0007 (4) | −0.0014 (4) |
C5 | 0.0335 (6) | 0.0188 (5) | 0.0187 (5) | −0.0007 (5) | −0.0012 (4) | −0.0023 (4) |
C6 | 0.0251 (5) | 0.0210 (5) | 0.0173 (4) | 0.0012 (4) | 0.0012 (4) | −0.0018 (4) |
C7 | 0.0248 (6) | 0.0338 (6) | 0.0246 (5) | 0.0006 (5) | 0.0004 (5) | −0.0030 (5) |
C8 | 0.0296 (7) | 0.0455 (8) | 0.0270 (6) | 0.0121 (6) | −0.0023 (5) | 0.0004 (6) |
C9 | 0.0443 (8) | 0.0312 (6) | 0.0279 (6) | 0.0138 (6) | 0.0034 (6) | 0.0058 (5) |
C10 | 0.0395 (7) | 0.0245 (6) | 0.0312 (6) | −0.0004 (6) | 0.0043 (6) | 0.0046 (5) |
C11 | 0.0260 (6) | 0.0244 (6) | 0.0241 (5) | −0.0005 (5) | −0.0003 (5) | 0.0012 (4) |
N1—C2 | 1.3463 (14) | C5—C6 | 1.5154 (16) |
N1—C3 | 1.4553 (15) | C5—H5A | 1.01 (2) |
N1—H1 | 0.86 (2) | C5—H5B | 0.96 (2) |
O1—C2 | 1.2439 (14) | C6—C7 | 1.3934 (18) |
O2—C4 | 1.3078 (15) | C6—C11 | 1.3976 (17) |
O2—H2 | 0.87 (2) | C7—C8 | 1.397 (2) |
O3—C4 | 1.2190 (16) | C7—H7 | 0.96 (2) |
C1—C2 | 1.5001 (17) | C8—C9 | 1.387 (2) |
C1—H1B | 0.97 (2) | C8—H8 | 0.93 (2) |
C1—H1C | 0.92 (2) | C9—C10 | 1.387 (2) |
C1—H1D | 0.98 (2) | C9—H9 | 0.94 (2) |
C3—C4 | 1.5316 (16) | C10—C11 | 1.3923 (18) |
C3—C5 | 1.5432 (15) | C10—H10 | 0.96 (2) |
C3—H3 | 0.996 (16) | C11—H11 | 0.962 (19) |
C2—N1—C3 | 120.54 (9) | C6—C5—H5A | 110.1 (11) |
C2—N1—H1 | 117.9 (12) | C3—C5—H5A | 109.9 (11) |
C3—N1—H1 | 120.4 (12) | C6—C5—H5B | 109.6 (11) |
C4—O2—H2 | 108.9 (16) | C3—C5—H5B | 106.3 (11) |
C2—C1—H1B | 109.7 (15) | H5A—C5—H5B | 108.0 (14) |
C2—C1—H1C | 113.9 (13) | C7—C6—C11 | 118.54 (11) |
H1B—C1—H1C | 107 (2) | C7—C6—C5 | 121.48 (11) |
C2—C1—H1D | 106.9 (14) | C11—C6—C5 | 119.95 (11) |
H1B—C1—H1D | 108.7 (18) | C6—C7—C8 | 120.65 (13) |
H1C—C1—H1D | 110.8 (18) | C6—C7—H7 | 121.5 (12) |
O1—C2—N1 | 120.22 (10) | C8—C7—H7 | 117.8 (12) |
O1—C2—C1 | 122.24 (10) | C9—C8—C7 | 120.14 (13) |
N1—C2—C1 | 117.53 (10) | C9—C8—H8 | 119.3 (12) |
N1—C3—C4 | 112.67 (9) | C7—C8—H8 | 120.6 (12) |
N1—C3—C5 | 110.88 (10) | C10—C9—C8 | 119.72 (13) |
C4—C3—C5 | 109.57 (9) | C10—C9—H9 | 121.8 (13) |
N1—C3—H3 | 108.2 (9) | C8—C9—H9 | 118.5 (13) |
C4—C3—H3 | 105.1 (9) | C9—C10—C11 | 120.13 (14) |
C5—C3—H3 | 110.3 (8) | C9—C10—H10 | 122.7 (12) |
O3—C4—O2 | 124.77 (12) | C11—C10—H10 | 117.2 (12) |
O3—C4—C3 | 121.67 (11) | C10—C11—C6 | 120.81 (12) |
O2—C4—C3 | 113.51 (10) | C10—C11—H11 | 120.4 (11) |
C6—C5—C3 | 112.71 (9) | C6—C11—H11 | 118.8 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3i | 0.86 (2) | 2.14 (2) | 2.9835 (11) | 171.3 (14) |
O2—H2···O1ii | 0.87 (2) | 1.74 (2) | 2.5502 (10) | 158.4 (18) |
Symmetry codes: (i) x+1, y, z; (ii) −x, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C11H13NO3 |
Mr | 207.22 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 158 |
a, b, c (Å) | 5.6528 (1), 11.1532 (2), 16.9897 (1) |
V (Å3) | 1071.15 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.54 × 0.14 × 0.12 |
Data collection | |
Diffractometer | CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15627, 1866, 1778 |
Rint | 0.019 |
(sin θ/λ)max (Å−1) | 0.714 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.028, 0.077, 1.08 |
No. of reflections | 1866 |
No. of parameters | 190 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.26, −0.18 |
Computer programs: SMART (Bruker, 1997), SMART, SHELXTL (Bruker, 1998), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3i | 0.86 (2) | 2.14 (2) | 2.9835 (11) | 171.3 (14) |
O2—H2···O1ii | 0.87 (2) | 1.74 (2) | 2.5502 (10) | 158.4 (18) |
Symmetry codes: (i) x+1, y, z; (ii) −x, y+1/2, −z+1/2. |
It is important to determine the crystal structures of amino acids and their derivatives because of their importance in defining the preferred conformations of large peptides and proteins. We have determined the structure of the title compound, (I), for a solid-state NMR tensor study. Few N15 chemical-shielding tensors have been determined (Harbison et al., 1984) and chemical-shielding tensors are important for accurate solution and solid-state NMR experiments (Oas et al., 1987; Hartzell et al., 1987; Lee & Ramamoorthy, 1998; Lee et al., 1998).