data_2011219
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2000
_journal_volume  56
_journal_page_first  1037
_journal_page_last  1039
_publ_section_title
;
Two key chiral intermediates in a new 4-hydroxyisoleucine synthesis
;
loop_
_publ_author_name
  'Kassem, Tarek'
  "Rolland, Val\'erie"
  'Martinez, Jean'
  'Rolland, Marc'
_chemical_formula_sum  'C16 H23 N O4 '
_chemical_formula_weight  293.363
_symmetry_cell_setting  'Orthorhombic'
_symmetry_space_group_name_H-M  'P 21 21 21'
loop_
_symmetry_equiv_pos_as_xyz
  '+X,+Y,+Z'
  '-X+ 1/2,-Y,+Z+ 1/2'
  '+X+ 1/2,-Y+ 1/2,-Z'
  '-X,+Y+ 1/2,-Z+ 1/2'
_cell_length_a  11.0434(5)
_cell_length_b  11.0028(3)
_cell_length_c  12.7460(6)
_cell_angle_alpha  90.0000(10)
_cell_angle_beta  90.0000(10)
_cell_angle_gamma  90.0000(10)
_cell_volume  1548.70(10)
_cell_formula_units_Z  4
_cell_measurement_temperature  298
_exptl_crystal_density_diffrn  1.258
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
  O1  .80675(4)  .35476(3)  .21678(3)  .0454(2) Uij 1.00
  O2  .79030(4)  .43003(4)  .05802(3)  .0531(2) Uij 1.00
  O3 1.02965(3)  .31680(4)  -.01746(3)  .0458(2) Uij 1.00
  O4  .74352(4)  .25746(4)  -.12923(3)  .0682(3) Uij 1.00
  N1  .94190(4)  .16070(4)  .14153(4)  .0403(3) Uij 1.00
  C1  .81495(5)  .34393(5)  .11209(4)  .0394(3) Uij 1.00
  C2  .85985(5)  .22308(5)  .07032(4)  .0354(3) Uij 1.00
  C3  .92549(4)  .24173(5)  -.03478(4)  .0372(3) Uij 1.00
  C4  .84108(5)  .30457(6)  -.11267(4)  .0435(3) Uij 1.00
  C5  .88272(6)  .41535(6)  -.17025(5)  .0526(4) Uij 1.00
  C6  .96583(6)  .12218(6)  -.08264(5)  .0527(4) Uij 1.00
  C7  .81782(4)  .24540(5)  .28220(4)  .0358(3) Uij 1.00
  C8  .92169(4)  .17113(5)  .23934(4)  .0349(3) Uij 1.00
  C9 1.01064(5)  .11875(6)  .31786(5)  .0488(3) Uij 1.00
  C10 1.01181(5)  .19512(6)  .41786(5)  .0486(3) Uij 1.00
  C11  .98768(6)  .32829(6)  .38611(5)  .0567(4) Uij 1.00
  C12  .85161(5)  .29493(5)  .38928(4)  .0435(3) Uij 1.00
  C13  .88557(5)  .19499(6)  .47131(4)  .0417(3) Uij 1.00
  C14  .88872(7)  .25258(8)  .58073(5)  .0682(5) Uij 1.00
  C15  .81863(6)  .07469(6)  .48100(5)  .0552(4) Uij 1.00
  C16  .69496(6)  .18218(8)  .27725(5)  .0594(4) Uij 1.00
  H2  .789655  .172897  .060137  .055054 Uiso 1.00
  H3 1.086861  .274144  .031634  .064080 Uiso 1.00
  H5A  .818946  .443908  -.214066  .072486 Uiso 1.00
  H5B  .952193  .394827  -.211819  .072486 Uiso 1.00
  H5C  .904571  .477024  -.120220  .072486 Uiso 1.00
  H6A 1.019013  .079571  -.035249  .071377 Uiso 1.00
  H6B 1.007233  .138122  -.146912  .071377 Uiso 1.00
  H6C  .895823  .072345  -.096054  .071377 Uiso 1.00
  H9A 1.090191  .118931  .287221  .069343 Uiso 1.00
  H9B  .987583  .037246  .334680  .069343 Uiso 1.00
  H10 1.080778  .175240  .459295  .068900 Uiso 1.00
  H11A 1.008392  .353761  .316296  .077001 Uiso 1.00
  H11B 1.004831  .392641  .434582  .077001 Uiso 1.00
  H12  .791950  .353332  .410708  .061869 Uiso 1.00
  H14A  .929820  .329083  .577722  .083805 Uiso 1.00
  H14B  .931335  .198899  .627686  .083805 Uiso 1.00
  H14C  .807674  .263939  .605398  .083805 Uiso 1.00
  H15A  .815119  .037199  .412832  .076024 Uiso 1.00
  H15B  .737792  .088085  .506159  .076024 Uiso 1.00
  H15C  .861454  .023045  .528446  .076024 Uiso 1.00
  H16A  .682090  .153401  .207517  .076153 Uiso 1.00
  H16B  .632343  .238472  .296269  .076153 Uiso 1.00
  H16C  .694916  .115135  .325470  .076153 Uiso 1.00
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
  O1  .0540(2)  .0419(2)  .0402(2)  .0178(2)  .0002(2)  .0014(2)
  O2  .0627(3)  .0482(3)  .0484(2)  .0192(2) -.0005(2)  .0083(2)
  O3  .0324(2)  .0466(3)  .0584(3) -.0092(2) -.0039(2)  .0082(2)
  O4  .0445(2)  .0962(4)  .0640(3) -.0136(3) -.0147(2)  .0057(3)
  N1  .0392(3)  .0384(3)  .0433(3)  .0068(2)  .0018(2)  .0011(2)
  C1  .0309(3)  .0437(4)  .0434(3)  .0045(3) -.0003(3) -.0004(3)
  C2  .0305(3)  .0355(4)  .0401(3) -.0005(2) -.0018(2) -.0019(3)
  C3  .0295(3)  .0367(3)  .0453(3) -.0040(3)  .0019(3) -.0002(3)
  C4  .0376(3)  .0528(4)  .0401(3)  .0013(3)  .0021(3) -.0006(3)
  C5  .0500(4)  .0559(4)  .0521(4)  .0068(3)  .0009(3)  .0084(4)
  C6  .0515(4)  .0485(4)  .0581(4) -.0016(3)  .0123(4) -.0062(3)
  C7  .0315(3)  .0375(3)  .0384(3)  .0051(3) -.0022(2)  .0027(3)
  C8  .0282(3)  .0293(3)  .0471(3)  .0013(2) -.0005(2) -.0006(3)
  C9  .0382(3)  .0588(4)  .0493(4)  .0185(3) -.0024(3)  .0058(3)
  C10  .0323(3)  .0615(4)  .0519(4)  .0016(3) -.0133(3)  .0015(3)
  C11  .0604(4)  .0536(4)  .0561(4) -.0218(3) -.0127(3) -.0021(4)
  C12  .0473(3)  .0398(4)  .0432(3)  .0106(3) -.0045(3) -.0053(3)
  C13  .0394(3)  .0467(4)  .0390(3)  .0041(3) -.0062(3) -.0016(3)
  C14  .0725(5)  .0864(6)  .0457(4)  .0108(5) -.0112(4) -.0052(4)
  C15  .0503(4)  .0564(4)  .0590(4) -.0039(3) -.0064(3)  .0115(4)
  C16  .0314(3)  .0943(6)  .0527(4) -.0119(4) -.0045(3)  .0048(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  O1 C1 . . 1.3427(6) yes
  O1 C7 . . 1.4691(6) yes
  O2 C1 . . 1.2028(6) yes
  O3 C3 . . 1.4332(6) yes
  O4 C4 . . 1.2141(6) yes
  N1 C2 . . 1.4546(6) yes
  N1 C8 . . 1.2716(6) yes
  C1 C2 . . 1.5158(7) yes
  C2 C3 . . 1.5370(7) yes
  C3 C4 . . 1.5273(7) yes
  C3 C6 . . 1.5168(8) yes
  C4 C5 . . 1.4952(8) yes
  C7 C8 . . 1.5106(7) yes
  C7 C12 . . 1.5162(7) no
  C7 C16 . . 1.5260(8) no
  C8 C9 . . 1.5161(7) no
  C9 C10 . . 1.5268(8) no
  C10 C11 . . 1.5432(9) no
  C10 C13 . . 1.5517(7) no
  C11 C12 . . 1.5474(8) no
  C12 C13 . . 1.5631(7) no
  C13 C14 . . 1.5322(8) no
  C13 C15 . . 1.5211(8) no