data_2011262
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2000
_journal_volume  56
_journal_page_first  e354
_journal_page_last  e355
_publ_section_title
;
(+)-(2R,3S)-3-Bromo-2-chloro-N,N-diisopropyl-3-phenylpropanamide and
(+)-(2R,3S)-3-bromo-2-chloro-N-(4-nitrophenyl)-3-phenylpropanamide
;
loop_
_publ_author_name
  'Chan, Bun'
  'Wong Leh See, Elicia'
  'Simpson, Jim'
  'Tan, Eng Wui'
_chemical_formula_moiety  'C15 H21 Br Cl N O'
_chemical_formula_sum  'C15 H21 Br Cl N O'
_chemical_formula_weight  346.69
_symmetry_cell_setting  Tetragonal
_symmetry_space_group_name_H-M  'P 41'
_symmetry_space_group_name_Hall  'P 41'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, z+1/2'
  '-y, x, z+1/4'
  'y, -x, z+3/4'
_cell_length_a  8.8863(19)
_cell_length_b  8.8863(19)
_cell_length_c  21.299(6)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  1681.9(7)
_cell_formula_units_Z  4
_cell_measurement_temperature  168(2)
_exptl_crystal_density_diffrn  1.369
_diffrn_ambient_temperature  168(2)
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_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
  C9  .2529(7)  .3014(8)  .2412(3)  .0378(15) Uani d . 1 . . C
  H9  .3204  .3563  .2672  .045 Uiso calc R 1 . . H
  C8  .1234(7)  .2365(6)  .2677(4)  .0370(15) Uani d . 1 . . C
  H8  .1034  .2460  .3113  .044 Uiso calc R 1 . . H
  C7  .0249(7)  .1580(7)  .2287(4)  .0428(17) Uani d . 1 . . C
  H7  -.0631  .1138  .2460  .051 Uiso calc R 1 . . H
  C6  .0527(7)  .1433(7)  .1658(4)  .0452(17) Uani d . 1 . . C
  H6  -.0150  .0889  .1397  .054 Uiso calc R 1 . . H
  C5  .1819(8)  .2094(8)  .1403(3)  .0453(18) Uani d . 1 . . C
  H5  .2007  .2016  .0965  .054 Uiso calc R 1 . . H
  C4  .2831(6)  .2863(6)  .1783(3)  .0340(14) Uani d . 1 . . C
  C3  .4227(7)  .3485(7)  .1487(4)  .0394(15) Uani d . 1 . . C
  H3  .4101  .3467  .1020  .047 Uiso calc R 1 . . H
  Br1  .60110(8)  .22026(8)  .17171(4)  .0526(3) Uani d . 1 . . Br
  C2  .4730(6)  .5055(6)  .1684(3)  .0311(13) Uani d . 1 . . C
  H2  .5049  .5061  .2134  .037 Uiso calc R 1 . . H
  Cl1  .30793(16)  .63876(15)  .15554(7)  .0349(3) Uani d . 1 . . Cl
  C1  .6018(6)  .5636(6)  .1256(3)  .0248(12) Uani d . 1 . . C
  O1  .5841(4)  .5456(4)  .0697(2)  .0322(9) Uani d . 1 . . O
  N1  .7241(5)  .6319(5)  .1517(2)  .0279(11) Uani d . 1 . . N
  C10  .7523(7)  .6510(6)  .2187(3)  .0325(14) Uani d . 1 . . C
  H10  .6579  .6223  .2412  .039 Uiso calc R 1 . . H
  C12  .7864(7)  .8144(7)  .2356(4)  .0414(16) Uani d . 1 . . C
  H12A  .8869  .8412  .2204  .062 Uiso calc R 1 . . H
  H12B  .7825  .8267  .2813  .062 Uiso calc R 1 . . H
  H12C  .7114  .8803  .2160  .062 Uiso calc R 1 . . H
  C13  .8445(7)  .6878(7)  .1073(3)  .0335(14) Uani d . 1 . . C
  H13  .9268  .7274  .1347  .040 Uiso calc R 1 . . H
  C14  .9157(8)  .5626(9)  .0689(4)  .0503(19) Uani d . 1 . . C
  H14A  .9240  .4718  .0948  .075 Uiso calc R 1 . . H
  H14B 1.0162  .5939  .0552  .075 Uiso calc R 1 . . H
  H14C  .8530  .5414  .0322  .075 Uiso calc R 1 . . H
  C15  .7901(8)  .8216(8)  .0695(4)  .0460(17) Uani d . 1 . . C
  H15A  .7153  .7881  .0387  .069 Uiso calc R 1 . . H
  H15B  .8754  .8677  .0476  .069 Uiso calc R 1 . . H
  H15C  .7443  .8955  .0978  .069 Uiso calc R 1 . . H
  C11  .8758(9)  .5444(7)  .2410(4)  .0481(18) Uani d . 1 . . C
  H52A  .8433  .4401  .2348  .072 Uiso calc R 1 . . H
  H52B  .8954  .5618  .2857  .072 Uiso calc R 1 . . H
  H52C  .9679  .5630  .2170  .072 Uiso calc R 1 . . H
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
  C9  .032(3)  .043(4)  .038(4)  -.014(3)  -.006(3)  .005(3)
  C8  .038(3)  .027(3)  .045(4)  -.007(3)  .001(3)  .009(3)
  C7  .032(3)  .027(3)  .070(5)  -.012(3)  .005(3)  .006(3)
  C6  .037(3)  .041(3)  .057(5)  -.016(3)  -.007(4)  -.005(3)
  C5  .046(4)  .050(4)  .040(4)  -.020(3)  .002(3)  -.007(3)
  C4  .031(3)  .035(3)  .036(4)  -.009(2)  -.006(3)  .001(3)
  C3  .048(4)  .029(3)  .042(4)  .000(3)  -.001(3)  .000(3)
  Br1  .0406(4)  .0424(4)  .0750(6)  .0072(3)  .0061(4)  .0081(4)
  C2  .026(3)  .034(3)  .034(4)  -.008(2)  -.002(3)  -.002(3)
  Cl1  .0395(8)  .0310(7)  .0343(8)  -.0067(6)  .0059(7)  .0054(6)
  C1  .027(3)  .027(3)  .020(3)  -.001(2)  .000(2)  .005(2)
  O1  .027(2)  .036(2)  .033(3)  -.0089(17)  -.0031(18)  .0037(19)
  N1  .026(2)  .025(2)  .033(3)  -.0025(19)  .004(2)  .006(2)
  C10  .036(3)  .030(3)  .031(4)  -.013(3)  -.005(3)  .001(3)
  C12  .034(3)  .035(3)  .055(5)  -.008(3)  -.002(3)  -.011(3)
  C13  .024(3)  .037(3)  .040(4)  -.009(3)  .001(3)  -.001(3)
  C14  .031(3)  .062(5)  .057(5)  -.009(3)  .018(3)  -.002(4)
  C15  .050(4)  .037(4)  .052(5)  -.015(3)  .005(3)  .012(3)
  C11  .056(4)  .035(4)  .054(5)  -.002(3)  -.018(4)  .002(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  C9 C4 . 1.373(10) ?
  C9 C8 . 1.405(9) ?
  C8 C7 . 1.395(10) ?
  C7 C6 . 1.367(11) ?
  C6 C5 . 1.399(9) ?
  C5 C4 . 1.389(9) ?
  C4 C3 . 1.498(9) y
  C3 C2 . 1.525(8) y
  C3 Br1 . 2.013(7) y
  C2 C1 . 1.551(8) y
  C2 Cl1 . 1.905(6) y
  C1 O1 . 1.213(7) y
  C1 N1 . 1.363(7) y
  N1 C10 . 1.458(8) ?
  N1 C13 . 1.513(7) ?
  C10 C11 . 1.525(10) ?
  C10 C12 . 1.526(8) ?
  C13 C15 . 1.514(9) ?
  C13 C14 . 1.518(9) ?