Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801012636/bt6054sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801012636/bt6054Isup2.hkl |
CCDC reference: 170935
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.040
- wR factor = 0.096
- Data-to-parameter ratio = 9.2
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 28.01 From the CIF: _reflns_number_total 1099 Count of symmetry unique reflns 1100 Completeness (_total/calc) 99.91% 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 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.
The title compound was prepared and recrystallized by Zeng (2000) according to the following procedure. L-trans 4-hydroxyproline (with nitrogen protected) and L-alanine methyl ester hydrochloride were reacted in 1:1 chloroform/acetronitrile following the method of Carpino (1986). The reaction was quenched with water and normal work-up of the organic layer afforded the title compound. Crystals were obtained from chloroform solutions.
Friedel-pair reflections were merged before final refinement because molybdenum radiation was employed and no atoms heavier than silicon are present in this structure. The absolute structure parameter (Flack parameter and its associated error) was -1.0 with an s.u. of 18.
Data collection: Please provide; cell refinement: Please provide; data reduction: Please provide; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997).
C8H12N2O3 | F(000) = 196 |
Mr = 184.20 | Dx = 1.420 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71070 Å |
a = 8.626 (2) Å | Cell parameters from 16 reflections |
b = 9.924 (3) Å | θ = 11–13° |
c = 5.179 (1) Å | µ = 0.11 mm−1 |
β = 103.719 (9)° | T = 293 K |
V = 430.70 (18) Å3 | Prism, colorless |
Z = 2 | 0.45 × 0.30 × 0.20 mm |
MAKER? four-circle diffractometer | Rint = 0.035 |
Radiation source: fine-focus sealed tube | θmax = 28.0°, θmin = 2.4° |
None monochromator | h = −9→11 |
θ/2θ scans | k = −10→13 |
2100 measured reflections | l = −6→4 |
1099 independent reflections | 3 standard reflections every 150 reflections |
835 reflections with I > 2σ(I) | intensity decay: <1% |
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)] = 0.040 | H-atom parameters constrained |
wR(F2) = 0.096 | w = 1/[σ2(Fo2) + (0.0264P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.99 | (Δ/σ)max < 0.001 |
1099 reflections | Δρmax = 0.20 e Å−3 |
120 parameters | Δρmin = −0.18 e Å−3 |
1 restraint | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.074 (13) |
C8H12N2O3 | V = 430.70 (18) Å3 |
Mr = 184.20 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 8.626 (2) Å | µ = 0.11 mm−1 |
b = 9.924 (3) Å | T = 293 K |
c = 5.179 (1) Å | 0.45 × 0.30 × 0.20 mm |
β = 103.719 (9)° |
MAKER? four-circle diffractometer | Rint = 0.035 |
2100 measured reflections | 3 standard reflections every 150 reflections |
1099 independent reflections | intensity decay: <1% |
835 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.040 | 1 restraint |
wR(F2) = 0.096 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.20 e Å−3 |
1099 reflections | Δρmin = −0.18 e Å−3 |
120 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 | ||
C1 | 0.2467 (3) | 0.6102 (3) | 0.3226 (5) | 0.0347 (6) | |
C2 | −0.0077 (3) | 0.4887 (3) | 0.2753 (5) | 0.0342 (6) | |
H2 | −0.0731 | 0.5261 | 0.1098 | 0.041* | |
C3 | 0.0726 (3) | 0.3612 (3) | 0.2082 (5) | 0.0325 (6) | |
C4 | 0.2801 (3) | 0.5138 (3) | 0.1155 (5) | 0.0325 (6) | |
H4 | 0.2393 | 0.5525 | −0.0617 | 0.039* | |
C5 | 0.4557 (4) | 0.4786 (3) | 0.1508 (6) | 0.0408 (7) | |
H5A | 0.5094 | 0.4739 | 0.3377 | 0.049* | |
H5B | 0.5092 | 0.5449 | 0.0648 | 0.049* | |
C6 | 0.4536 (3) | 0.3413 (3) | 0.0187 (6) | 0.0390 (7) | |
H6 | 0.5517 | 0.2911 | 0.0942 | 0.047* | |
C7 | 0.3088 (4) | 0.2714 (3) | 0.0811 (7) | 0.0444 (7) | |
H7A | 0.2542 | 0.2162 | −0.0674 | 0.053* | |
H7B | 0.3406 | 0.2149 | 0.2375 | 0.053* | |
C8 | −0.1152 (4) | 0.4593 (3) | 0.4595 (8) | 0.0524 (8) | |
H8A | −0.1638 | 0.5415 | 0.4984 | 0.079* | |
H8B | −0.0534 | 0.4209 | 0.6216 | 0.079* | |
H8C | −0.1966 | 0.3969 | 0.3758 | 0.079* | |
N1 | 0.1110 (3) | 0.5890 (2) | 0.3947 (4) | 0.0350 (5) | |
H1 | 0.0918 | 0.6379 | 0.5206 | 0.042* | |
N2 | 0.2062 (3) | 0.3816 (2) | 0.1281 (4) | 0.0342 (5) | |
O1 | 0.3407 (3) | 0.7007 (2) | 0.4120 (4) | 0.0514 (6) | |
O2 | 0.0168 (2) | 0.24882 (19) | 0.2236 (4) | 0.0466 (6) | |
O3 | 0.4307 (3) | 0.3558 (3) | −0.2594 (4) | 0.0625 (7) | |
H3 | 0.4828 | 0.2984 | −0.3154 | 0.075* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0388 (15) | 0.0284 (13) | 0.0396 (15) | 0.0003 (11) | 0.0148 (11) | 0.0010 (11) |
C2 | 0.0323 (14) | 0.0318 (14) | 0.0383 (14) | 0.0023 (11) | 0.0076 (11) | −0.0003 (11) |
C3 | 0.0348 (14) | 0.0324 (14) | 0.0303 (13) | −0.0034 (11) | 0.0076 (10) | −0.0002 (11) |
C4 | 0.0400 (14) | 0.0284 (12) | 0.0324 (13) | 0.0000 (11) | 0.0149 (11) | 0.0017 (11) |
C5 | 0.0385 (15) | 0.0388 (15) | 0.0511 (16) | −0.0005 (12) | 0.0225 (13) | 0.0014 (13) |
C6 | 0.0381 (15) | 0.0413 (16) | 0.0395 (15) | 0.0094 (12) | 0.0130 (12) | 0.0044 (12) |
C7 | 0.0502 (16) | 0.0330 (15) | 0.0531 (19) | 0.0011 (13) | 0.0188 (14) | −0.0092 (13) |
C8 | 0.0410 (16) | 0.0476 (17) | 0.077 (2) | −0.0074 (14) | 0.0311 (16) | −0.0152 (17) |
N1 | 0.0391 (13) | 0.0283 (12) | 0.0417 (13) | −0.0034 (10) | 0.0179 (10) | −0.0077 (9) |
N2 | 0.0375 (12) | 0.0265 (11) | 0.0412 (13) | −0.0003 (10) | 0.0142 (9) | −0.0061 (10) |
O1 | 0.0528 (13) | 0.0426 (12) | 0.0674 (16) | −0.0181 (10) | 0.0313 (11) | −0.0189 (11) |
O2 | 0.0511 (12) | 0.0339 (11) | 0.0607 (15) | −0.0104 (9) | 0.0249 (11) | −0.0040 (9) |
O3 | 0.0801 (17) | 0.0728 (17) | 0.0421 (12) | 0.0356 (13) | 0.0295 (11) | 0.0071 (11) |
C1—O1 | 1.225 (3) | C5—H5A | 0.9700 |
C1—N1 | 1.327 (3) | C5—H5B | 0.9700 |
C1—C4 | 1.515 (3) | C6—O3 | 1.414 (4) |
C2—N1 | 1.456 (3) | C6—C7 | 1.529 (4) |
C2—C8 | 1.508 (4) | C6—H6 | 0.9800 |
C2—C3 | 1.522 (4) | C7—N2 | 1.463 (4) |
C2—H2 | 0.9800 | C7—H7A | 0.9700 |
C3—O2 | 1.225 (3) | C7—H7B | 0.9700 |
C3—N2 | 1.330 (3) | C8—H8A | 0.9600 |
C4—N2 | 1.467 (3) | C8—H8B | 0.9600 |
C4—C5 | 1.523 (4) | C8—H8C | 0.9600 |
C4—H4 | 0.9800 | N1—H1 | 0.8600 |
C5—C6 | 1.523 (4) | O3—H3 | 0.8200 |
O1—C1—N1 | 124.0 (2) | O3—C6—C7 | 109.7 (2) |
O1—C1—C4 | 120.7 (3) | C5—C6—C7 | 103.5 (2) |
N1—C1—C4 | 115.3 (2) | O3—C6—H6 | 110.9 |
N1—C2—C8 | 109.8 (2) | C5—C6—H6 | 110.9 |
N1—C2—C3 | 110.7 (2) | C7—C6—H6 | 110.9 |
C8—C2—C3 | 111.4 (2) | N2—C7—C6 | 104.7 (2) |
N1—C2—H2 | 108.3 | N2—C7—H7A | 110.8 |
C8—C2—H2 | 108.3 | C6—C7—H7A | 110.8 |
C3—C2—H2 | 108.3 | N2—C7—H7B | 110.8 |
O2—C3—N2 | 122.9 (3) | C6—C7—H7B | 110.8 |
O2—C3—C2 | 122.3 (2) | H7A—C7—H7B | 108.9 |
N2—C3—C2 | 114.8 (2) | C2—C8—H8A | 109.5 |
N2—C4—C1 | 112.1 (2) | C2—C8—H8B | 109.5 |
N2—C4—C5 | 102.7 (2) | H8A—C8—H8B | 109.5 |
C1—C4—C5 | 114.2 (2) | C2—C8—H8C | 109.5 |
N2—C4—H4 | 109.2 | H8A—C8—H8C | 109.5 |
C1—C4—H4 | 109.2 | H8B—C8—H8C | 109.5 |
C5—C4—H4 | 109.2 | C1—N1—C2 | 124.5 (2) |
C4—C5—C6 | 104.2 (2) | C1—N1—H1 | 117.7 |
C4—C5—H5A | 110.9 | C2—N1—H1 | 117.7 |
C6—C5—H5A | 110.9 | C3—N2—C4 | 124.6 (2) |
C4—C5—H5B | 110.9 | C3—N2—C7 | 122.7 (2) |
C6—C5—H5B | 110.9 | C4—N2—C7 | 112.0 (2) |
H5A—C5—H5B | 108.9 | C6—O3—H3 | 109.5 |
O3—C6—C5 | 110.5 (2) | ||
N1—C2—C3—O2 | 145.8 (3) | O1—C1—N1—C2 | 174.9 (3) |
C8—C2—C3—O2 | 23.3 (4) | C4—C1—N1—C2 | −4.7 (4) |
N1—C2—C3—N2 | −35.2 (3) | C8—C2—N1—C1 | 160.8 (2) |
C8—C2—C3—N2 | −157.7 (2) | C3—C2—N1—C1 | 37.4 (3) |
O1—C1—C4—N2 | 151.9 (3) | O2—C3—N2—C4 | −177.8 (3) |
N1—C1—C4—N2 | −28.5 (3) | C2—C3—N2—C4 | 3.2 (4) |
O1—C1—C4—C5 | 35.6 (4) | O2—C3—N2—C7 | −7.4 (4) |
N1—C1—C4—C5 | −144.7 (2) | C2—C3—N2—C7 | 173.6 (2) |
N2—C4—C5—C6 | 33.0 (3) | C1—C4—N2—C3 | 29.7 (4) |
C1—C4—C5—C6 | 154.5 (2) | C5—C4—N2—C3 | 152.7 (2) |
C4—C5—C6—O3 | 82.0 (3) | C1—C4—N2—C7 | −141.6 (3) |
C4—C5—C6—C7 | −35.5 (3) | C5—C4—N2—C7 | −18.5 (3) |
O3—C6—C7—N2 | −94.0 (3) | C6—C7—N2—C3 | −174.9 (2) |
C5—C6—C7—N2 | 23.9 (3) | C6—C7—N2—C4 | −3.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.86 | 2.10 | 2.945 (3) | 165 |
O3—H3···O1ii | 0.82 | 1.97 | 2.761 (3) | 163 |
Symmetry codes: (i) −x, y+1/2, −z+1; (ii) −x+1, y−1/2, −z. |
Experimental details
Crystal data | |
Chemical formula | C8H12N2O3 |
Mr | 184.20 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 293 |
a, b, c (Å) | 8.626 (2), 9.924 (3), 5.179 (1) |
β (°) | 103.719 (9) |
V (Å3) | 430.70 (18) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.45 × 0.30 × 0.20 |
Data collection | |
Diffractometer | MAKER? four-circle diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2100, 1099, 835 |
Rint | 0.035 |
(sin θ/λ)max (Å−1) | 0.661 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.096, 0.99 |
No. of reflections | 1099 |
No. of parameters | 120 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.18 |
Computer programs: Please provide, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.86 | 2.10 | 2.945 (3) | 165.2 |
O3—H3···O1ii | 0.82 | 1.97 | 2.761 (3) | 162.7 |
Symmetry codes: (i) −x, y+1/2, −z+1; (ii) −x+1, y−1/2, −z. |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
No comment