#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2011263.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2011263
_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 H12 Br Cl N2 O3'
_chemical_formula_sum  'C15 H12 Br Cl N2 O3'
_chemical_formula_weight  383.63
_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, y+1/2, -z+1/2'
  'x+1/2, -y+1/2, -z'
_cell_length_a  13.900(4)
_cell_length_b  14.648(5)
_cell_length_c  15.553(5)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  3166.8(17)
_cell_formula_units_Z  8
_cell_measurement_temperature  170(2)
_exptl_crystal_density_diffrn  1.609
_diffrn_ambient_temperature  170(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
  C19  .0566(2)  .3773(2)  .1383(2)  .0335(8) Uani d . 1 . . C
  H19  .0607  .3835  .0776  .040 Uiso calc R 1 . . H
  C18  .0403(2)  .4536(3)  .1884(2)  .0391(9) Uani d . 1 . . C
  H18  .0345  .5120  .1623  .047 Uiso calc R 1 . . H
  C17  .0326(3)  .4444(3)  .2773(2)  .0398(9) Uani d . 1 . . C
  H17  .0216  .4967  .3120  .048 Uiso calc R 1 . . H
  C16  .0407(2)  .3597(3)  .3148(2)  .0427(10) Uani d . 1 . . C
  H16  .0346  .3535  .3753  .051 Uiso calc R 1 . . H
  C15  .0579(2)  .2834(3)  .2643(2)  .0338(8) Uani d . 1 . . C
  H15  .0636  .2251  .2905  .041 Uiso calc R 1 . . H
  C14  .0669(2)  .2916(2)  .17542(19)  .0279(8) Uani d . 1 . . C
  C13  .0896(2)  .2086(2)  .1228(2)  .0298(8) Uani d . 1 . . C
  H13  .0888  .1540  .1614  .036 Uiso calc R 1 . . H
  Br11  .22035(2)  .22079(3)  .07224(3)  .04693(11) Uani d . 1 . . Br
  C12  .0237(2)  .1907(2)  .04730(19)  .0288(7) Uani d . 1 . . C
  H12  .0252  .2437  .0068  .035 Uiso calc R 1 . . H
  Cl11  -.09659(6)  .17288(6)  .08585(6)  .0444(2) Uani d . 1 . . Cl
  C11  .0487(2)  .1030(2)  -.0004(2)  .0290(7) Uani d . 1 . . C
  O11  .07335(18)  .03402(16)  .03619(15)  .0415(6) Uani d . 1 . . O
  N11  .03642(18)  .11036(16)  -.08716(16)  .0285(6) Uani d . 1 . . N
  H11A  .0233  .1656  -.1062  .034 Uiso calc R 1 . . H
  C110  .0418(2)  .0419(2)  -.1502(2)  .0247(7) Uani d . 1 . . C
  C111  .0417(2)  .0707(2)  -.2358(2)  .0277(8) Uani d . 1 . . C
  H111  .0421  .1341  -.2488  .033 Uiso calc R 1 . . H
  C112  .0409(2)  .0078(2)  -.3012(2)  .0291(8) Uani d . 1 . . C
  H112  .0399  .0269  -.3596  .035 Uiso calc R 1 . . H
  C113  .0417(2)  -.0832(2)  -.2806(2)  .0269(7) Uani d . 1 . . C
  N12  .0385(2)  -.1500(2)  -.3492(2)  .0381(7) Uani d . 1 . . N
  O121  .0379(2)  -.23186(19)  -.32907(17)  .0658(9) Uani d . 1 . . O
  O122  .03745(19)  -.12469(17)  -.42397(16)  .0501(7) Uani d . 1 . . O
  C114  .0428(2)  -.1136(2)  -.1959(2)  .0303(8) Uani d . 1 . . C
  H114  .0431  -.1771  -.1834  .036 Uiso calc R 1 . . H
  C115  .0435(2)  -.0508(2)  -.1306(2)  .0269(7) Uani d . 1 . . C
  H115  .0450  -.0704  -.0724  .032 Uiso calc R 1 . . H
  C29  .6858(2)  .8692(3)  .1582(2)  .0340(8) Uani d . 1 . . C
  H29  .6796  .8046  .1560  .041 Uiso calc R 1 . . H
  C28  .7066(3)  .9117(3)  .2352(2)  .0452(10) Uani d . 1 . . C
  H28  .7154  .8758  .2855  .054 Uiso calc R 1 . . H
  C27  .7146(3) 1.0045(3)  .2401(3)  .0510(11) Uani d . 1 . . C
  H27  .7275 1.0329  .2938  .061 Uiso calc R 1 . . H
  C26  .7040(3) 1.0563(3)  .1677(3)  .0494(11) Uani d . 1 . . C
  H26  .7110 1.1207  .1713  .059 Uiso calc R 1 . . H
  C25  .6829(2) 1.0156(2)  .0880(3)  .0391(9) Uani d . 1 . . C
  H25  .6748 1.0519  .0379  .047 Uiso calc R 1 . . H
  C24  .6741(2)  .9207(2)  .0841(2)  .0303(8) Uani d . 1 . . C
  C23  .6516(2)  .8769(2)  -.0006(2)  .0274(7) Uani d . 1 . . C
  H23  .6499  .9254  -.0458  .033 Uiso calc R 1 . . H
  Br21  .52362(2)  .81695(3)  .00453(2)  .04684(11) Uani d . 1 . . Br
  C22  .7214(2)  .8029(2)  -.02867(18)  .0263(7) Uani d . 1 . . C
  H22  .7233  .7530  .0152  .032 Uiso calc R 1 . . H
  Cl21  .83885(6)  .85410(7)  -.03951(6)  .0427(2) Uani d . 1 . . Cl
  C21  .6982(2)  .7631(2)  -.1174(2)  .0276(8) Uani d . 1 . . C
  O21  .67049(17)  .81173(15)  -.17529(14)  .0378(6) Uani d . 1 . . O
  N21  .71489(18)  .67149(16)  -.12412(15)  .0260(6) Uani d . 1 . . N
  H21A  .7302  .6432  -.0761  .031 Uiso calc R 1 . . H
  C210  .7106(2)  .6170(2)  -.19812(19)  .0239(7) Uani d . 1 . . C
  C211  .7207(2)  .5229(2)  -.1865(2)  .0257(7) Uani d . 1 . . C
  H211  .7281  .4985  -.1303  .031 Uiso calc R 1 . . H
  C212  .7199(2)  .4657(2)  -.2568(2)  .0296(8) Uani d . 1 . . C
  H212  .7268  .4017  -.2494  .036 Uiso calc R 1 . . H
  C213  .7090(2)  .5024(2)  -.3385(2)  .0281(7) Uani d . 1 . . C
  N22  .7106(2)  .4408(2)  -.4122(2)  .0425(8) Uani d . 1 . . N
  O222  .7211(2)  .3589(2)  -.39816(18)  .0645(8) Uani d . 1 . . O
  O221  .7015(2)  .47252(19)  -.48425(17)  .0646(8) Uani d . 1 . . O
  C214  .6984(2)  .5950(2)  -.3511(2)  .0318(8) Uani d . 1 . . C
  H214  .6908  .6187  -.4075  .038 Uiso calc R 1 . . H
  C215  .6989(2)  .6532(2)  -.2809(2)  .0303(8) Uani d . 1 . . C
  H215  .6913  .7172  -.2887  .036 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
  C19  .039(2)  .037(2)  .0251(19)  .0005(15)  .0059(15)  -.0011(17)
  C18  .036(2)  .035(2)  .047(2)  -.0007(16)  .0001(18)  -.0063(17)
  C17  .033(2)  .046(2)  .040(2)  -.0019(18)  .0013(17)  -.0223(19)
  C16  .038(2)  .067(3)  .0230(19)  -.001(2)  -.0008(16)  -.0140(19)
  C15  .0373(19)  .043(2)  .0216(18)  .0022(17)  .0003(14)  .0029(17)
  C14  .0286(16)  .034(2)  .0207(17)  -.0014(14)  .0011(13)  -.0068(15)
  C13  .0276(16)  .037(2)  .0246(18)  -.0002(15)  .0029(13)  .0010(15)
  Br11  .03405(18)  .0556(2)  .0512(2)  -.00105(18)  .00936(18)  -.0180(2)
  C12  .0332(16)  .0316(19)  .0215(17)  .0063(15)  .0003(14)  -.0001(14)
  Cl11  .0307(4)  .0540(6)  .0485(6)  -.0010(4)  .0026(4)  -.0198(5)
  C11  .0311(16)  .0309(19)  .0250(18)  .0035(13)  -.0017(16)  -.0001(17)
  O11  .0655(17)  .0336(15)  .0253(13)  .0126(12)  -.0102(12)  .0007(11)
  N11  .0452(16)  .0181(14)  .0221(16)  .0024(12)  -.0003(13)  .0023(12)
  C110  .0239(17)  .0281(19)  .0220(18)  .0004(14)  -.0020(14)  -.0046(14)
  C111  .0315(19)  .0264(18)  .0251(19)  .0029(15)  -.0018(14)  .0021(14)
  C112  .0313(18)  .033(2)  .0228(18)  .0039(15)  -.0027(15)  -.0008(15)
  C113  .0251(17)  .029(2)  .0263(19)  -.0017(15)  -.0003(14)  -.0038(15)
  N12  .0411(18)  .0360(19)  .037(2)  -.0061(14)  .0024(15)  -.0106(15)
  O121  .117(3)  .0322(17)  .0476(18)  -.0214(18)  -.0021(17)  -.0127(13)
  O122  .0764(18)  .0485(16)  .0255(15)  .0024(14)  -.0029(14)  -.0118(13)
  C114  .0348(19)  .0226(18)  .033(2)  -.0039(15)  -.0012(15)  .0038(15)
  C115  .0305(18)  .0263(19)  .0239(18)  -.0008(14)  -.0033(14)  .0020(14)
  C29  .0327(18)  .039(2)  .030(2)  .0016(15)  -.0033(15)  -.0031(17)
  C28  .039(2)  .065(3)  .032(2)  .007(2)  .0002(17)  -.0109(19)
  C27  .033(2)  .070(3)  .050(3)  .002(2)  -.001(2)  -.028(2)
  C26  .040(2)  .041(2)  .067(3)  -.0070(18)  .007(2)  -.027(2)
  C25  .0356(18)  .031(2)  .051(3)  -.0023(15)  .0084(17)  -.0113(18)
  C24  .0248(16)  .034(2)  .032(2)  .0007(14)  .0026(15)  -.0091(17)
  C23  .0271(15)  .0267(17)  .0284(18)  -.0026(12)  -.0021(15)  -.0016(16)
  Br21  .03060(17)  .0615(2)  .0485(2)  -.01033(17)  .00140(18)  -.0226(2)
  C22  .0349(16)  .0221(17)  .0220(17)  .0025(15)  -.0039(14)  .0006(13)
  Cl21  .0279(4)  .0629(6)  .0372(5)  -.0019(4)  .0014(4)  -.0105(4)
  C21  .0340(18)  .024(2)  .0248(19)  .0018(14)  .0057(14)  .0019(14)
  O21  .0619(15)  .0274(13)  .0239(13)  .0072(12)  -.0080(11)  .0017(11)
  N21  .0407(15)  .0225(15)  .0147(14)  .0037(13)  -.0003(12)  .0035(11)
  C210  .0259(16)  .0248(18)  .0211(18)  .0011(14)  .0041(14)  .0011(13)
  C211  .0276(16)  .0267(19)  .0228(18)  -.0017(15)  .0012(15)  .0025(13)
  C212  .0248(16)  .0260(18)  .038(2)  -.0003(15)  .0045(16)  -.0024(15)
  C213  .0278(17)  .0317(19)  .0249(19)  -.0016(15)  .0046(15)  -.0115(15)
  N22  .0380(17)  .053(2)  .037(2)  -.0090(15)  .0104(15)  -.0136(16)
  O222  .087(2)  .0435(18)  .063(2)  .0130(17)  -.0067(17)  -.0252(14)
  O221  .098(2)  .0695(19)  .0259(17)  -.0237(17)  .0190(16)  -.0141(14)
  C214  .0358(19)  .038(2)  .0214(19)  -.0014(15)  .0032(14)  .0017(15)
  C215  .047(2)  .0236(18)  .0204(18)  .0030(15)  .0036(15)  .0001(14)
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
  C19 C18 . 1.381(5) ?
  C19 C14 . 1.389(5) ?
  C18 C17 . 1.393(5) ?
  C17 C16 . 1.376(5) ?
  C16 C15 . 1.387(5) ?
  C15 C14 . 1.393(4) ?
  C14 C13 . 1.498(4) y
  C13 C12 . 1.513(4) y
  C13 Br11 . 1.988(3) y
  C12 C11 . 1.524(4) y
  C12 Cl11 . 1.796(3) y
  C11 O11 . 1.210(4) y
  C11 N11 . 1.364(4) y
  N11 C110 . 1.405(4) y
  C110 C115 . 1.392(4) ?
  C110 C111 . 1.396(4) ?
  C111 C112 . 1.373(4) ?
  C112 C113 . 1.371(5) ?
  C113 C114 . 1.391(4) ?
  C113 N12 . 1.448(4) ?
  N12 O122 . 1.220(4) ?
  N12 O121 . 1.240(4) ?
  C114 C115 . 1.370(4) ?
  C29 C28 . 1.379(5) ?
  C29 C24 . 1.388(5) ?
  C28 C27 . 1.367(6) ?
  C27 C26 . 1.366(6) ?
  C26 C25 . 1.407(5) ?
  C25 C24 . 1.396(4) ?
  C24 C23 . 1.498(4) y
  C23 C22 . 1.519(4) y
  C23 Br21 . 1.986(3) y
  C22 C21 . 1.532(4) y
  C22 Cl21 . 1.805(3) y
  C21 O21 . 1.211(4) y
  C21 N21 . 1.366(4) y
  N21 C210 . 1.402(4) y
  C210 C211 . 1.397(4) ?
  C210 C215 . 1.402(4) ?
  C211 C212 . 1.378(4) ?
  C212 C213 . 1.389(4) ?
  C213 C214 . 1.378(5) ?
  C213 N22 . 1.458(4) ?
  N22 O221 . 1.220(4) ?
  N22 O222 . 1.228(4) ?
  C214 C215 . 1.386(4) ?