#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012771.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_2012771
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o362
_journal_page_last  o364
_publ_section_title
;
(1R)-2-[(3R,4S)-3-Methyl-4-(N-phenyl-N-propionylamino)pyridyl]-1-
phenylethyl p-bromobenzoate and
N-{(3R,4S)1-[(2S)-2-(4-bromophenyl)-2-hydroxyethyl]-3-methyl-4-pyridyl}-
N-phenylpropenamide
;
loop_
_publ_author_name
  'Deschamps, Jeffrey R.'
  'George, Clifford'
  'Flippen-Anderson, Judith L.'
_chemical_formula_moiety  'C23 H27 Br N2 O2'
_chemical_formula_sum  'C23 H27 Br N2 O2'
_chemical_formula_iupac  'C23 H27 Br N2 O2'
_chemical_formula_weight  443.38
_symmetry_cell_setting  Orthorhombic
_symmetry_space_group_name_H-M  'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
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  6.19320(10)
_cell_length_b  10.74610(10)
_cell_length_c  33.0458(3)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  2199.29(5)
_cell_formula_units_Z  4
_cell_measurement_temperature  295(2)
_exptl_crystal_density_diffrn  1.339
_diffrn_ambient_temperature  295(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
  Br1 0.37695(7) 0.64565(3) 0.904840(11) 0.09159(19) Uani d . 1 . . Br
  N1 0.3654(4) 1.16624(19) 1.08489(6) 0.0602(5) Uani d . 1 . . N
  C2 0.3255(5) 1.1133(2) 1.12504(8) 0.0638(6) Uani d . 1 . . C
  H2A 0.4160 1.0406 1.1288 0.077 Uiso calc R 1 . . H
  H2B 0.1760 1.0871 1.1269 0.077 Uiso calc R 1 . . H
  C3 0.3731(5) 1.2076(3) 1.15828(7) 0.0629(6) Uani d . 1 . . C
  H3A 0.3327 1.1692 1.1841 0.075 Uiso calc R 1 . . H
  C3' 0.6091(6) 1.2382(4) 1.16058(14) 0.1041(13) Uani d . 1 . . C
  H3'A 0.6329 1.2983 1.1816 0.156 Uiso calc R 1 . . H
  H3'B 0.6561 1.2719 1.1352 0.156 Uiso calc R 1 . . H
  H3'C 0.6895 1.1640 1.1664 0.156 Uiso calc R 1 . . H
  C4 0.2237(4) 1.3200(2) 1.15186(7) 0.0541(5) Uani d . 1 . . C
  H4A 0.0764 1.2867 1.1513 0.065 Uiso calc R 1 . . H
  C5 0.2631(6) 1.3751(3) 1.11030(9) 0.0749(8) Uani d . 1 . . C
  H5A 0.4094 1.4070 1.1087 0.090 Uiso calc R 1 . . H
  H5B 0.1642 1.4436 1.1056 0.090 Uiso calc R 1 . . H
  C6 0.2293(6) 1.2747(3) 1.07822(8) 0.0774(8) Uani d . 1 . . C
  H6A 0.0791 1.2490 1.0784 0.093 Uiso calc R 1 . . H
  H6B 0.2606 1.3093 1.0518 0.093 Uiso calc R 1 . . H
  N7 0.2294(3) 1.41064(19) 1.18537(6) 0.0557(5) Uani d . 1 . . N
  C8 0.1118(4) 1.3829(2) 1.21924(7) 0.0563(5) Uani d . 1 . . C
  O8 0.0186(3) 1.28299(19) 1.22270(6) 0.0698(5) Uani d . 1 . . O
  C9 0.0951(5) 1.4798(3) 1.25136(9) 0.0704(7) Uani d . 1 . . C
  H9 0.1583 1.5574 1.2475 0.084 Uiso calc R 1 . . H
  C10 -0.0074(6) 1.4561(4) 1.28480(10) 0.0883(10) Uani d . 1 . . C
  H10A -0.0706 1.3786 1.2887 0.106 Uiso calc R 1 . . H
  H10B -0.0176 1.5167 1.3048 0.106 Uiso calc R 1 . . H
  C1A 0.3446(4) 1.5269(2) 1.18228(8) 0.0579(5) Uani d . 1 . . C
  C2A 0.5383(5) 1.5417(3) 1.20331(10) 0.0758(8) Uani d . 1 . . C
  H2AA 0.5987 1.4755 1.2174 0.091 Uiso calc R 1 . . H
  C3A 0.6386(6) 1.6562(4) 1.20279(13) 0.0941(10) Uani d . 1 . . C
  H3AA 0.7652 1.6677 1.2174 0.113 Uiso calc R 1 . . H
  C4A 0.5542(6) 1.7533(3) 1.18097(12) 0.0896(10) Uani d . 1 . . C
  H4AA 0.6249 1.8296 1.1805 0.108 Uiso calc R 1 . . H
  C5A 0.3658(7) 1.7376(3) 1.15988(10) 0.0835(9) Uani d . 1 . . C
  H5AA 0.3096 1.8032 1.1449 0.100 Uiso calc R 1 . . H
  C6A 0.2588(5) 1.6247(3) 1.16082(9) 0.0673(7) Uani d . 1 . . C
  H6AA 0.1292 1.6150 1.1470 0.081 Uiso calc R 1 . . H
  C1' 0.3335(5) 1.0728(3) 1.05314(8) 0.0664(7) Uani d . 1 . . C
  H1'A 0.1810 1.0670 1.0467 0.080 Uiso calc R 1 . . H
  H1'B 0.3807 0.9922 1.0629 0.080 Uiso calc R 1 . . H
  C2' 0.4597(5) 1.1063(3) 1.01494(8) 0.0683(7) Uani d . 1 . . C
  H2'A 0.3947 1.1798 1.0023 0.082 Uiso calc R 1 . . H
  O2' 0.6772(4) 1.1330(2) 1.02556(7) 0.0846(6) Uani d . 1 . . O
  H2' 0.683(7) 1.161(4) 1.0484(14) 0.101 Uiso d . 1 . . H
  C1B 0.4506(5) 0.9983(3) 0.98571(8) 0.0637(6) Uani d . 1 . . C
  C6B 0.6066(6) 0.9079(3) 0.98542(9) 0.0741(7) Uani d . 1 . . C
  H6BA 0.7273 0.9164 1.0019 0.089 Uiso calc R 1 . . H
  C5B 0.5869(6) 0.8037(3) 0.96088(9) 0.0786(8) Uani d . 1 . . C
  H5BA 0.6937 0.7428 0.9608 0.094 Uiso calc R 1 . . H
  C4B 0.4094(5) 0.7918(3) 0.93692(8) 0.0680(7) Uani d . 1 . . C
  C3B 0.2531(6) 0.8811(3) 0.93587(11) 0.0831(9) Uani d . 1 . . C
  H3BA 0.1336 0.8724 0.9191 0.100 Uiso calc R 1 . . H
  C2B 0.2756(6) 0.9852(3) 0.96038(10) 0.0799(8) Uani d . 1 . . C
  H2BA 0.1707 1.0471 0.9597 0.096 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
  Br1 0.1223(3) 0.0756(2) 0.0769(2) 0.01214(19) -0.00236(19) -0.01571(16)
  N1 0.0760(13) 0.0550(11) 0.0498(10) -0.0080(10) 0.0017(9) 0.0027(8)
  C2 0.0817(17) 0.0552(13) 0.0545(13) -0.0047(11) 0.0037(11) 0.0039(11)
  C3 0.0745(15) 0.0626(14) 0.0515(12) 0.0012(13) -0.0071(12) 0.0051(11)
  C3' 0.068(2) 0.120(3) 0.124(3) 0.021(2) -0.034(2) -0.043(2)
  C4 0.0502(12) 0.0585(14) 0.0536(12) -0.0074(9) -0.0042(9) -0.0026(10)
  C5 0.111(2) 0.0612(16) 0.0526(12) 0.0103(15) -0.0049(14) 0.0001(12)
  C6 0.111(2) 0.0703(17) 0.0512(13) 0.0125(16) -0.0116(14) -0.0016(13)
  N7 0.0622(11) 0.0546(11) 0.0504(10) -0.0065(8) -0.0036(9) 0.0005(9)
  C8 0.0565(12) 0.0600(13) 0.0524(12) 0.0016(11) -0.0050(10) 0.0032(10)
  O8 0.0745(12) 0.0695(12) 0.0655(11) -0.0136(9) 0.0042(9) 0.0035(9)
  C9 0.0850(18) 0.0662(14) 0.0601(14) 0.0046(14) 0.0054(14) -0.0034(12)
  C10 0.106(2) 0.083(2) 0.075(2) 0.0128(18) 0.0225(18) -0.0048(17)
  C1A 0.0620(14) 0.0556(12) 0.0561(12) -0.0056(10) -0.0015(10) -0.0045(11)
  C2A 0.0722(17) 0.0711(17) 0.0841(19) -0.0080(13) -0.0191(14) -0.0088(15)
  C3A 0.081(2) 0.095(2) 0.106(2) -0.0223(19) -0.0166(18) -0.024(2)
  C4A 0.100(2) 0.0711(19) 0.098(2) -0.0279(17) 0.0132(19) -0.0112(18)
  C5A 0.109(2) 0.0616(16) 0.0797(18) -0.0117(18) 0.0044(19) 0.0041(14)
  C6A 0.0739(16) 0.0617(16) 0.0664(15) -0.0038(13) -0.0034(12) -0.0007(13)
  C1' 0.0823(17) 0.0607(14) 0.0562(13) -0.0111(12) 0.0082(12) -0.0051(12)
  C2' 0.0871(19) 0.0646(15) 0.0532(13) -0.0026(13) 0.0036(12) 0.0049(12)
  O2' 0.0914(15) 0.0886(15) 0.0736(12) -0.0244(12) 0.0116(11) -0.0032(12)
  C1B 0.0771(16) 0.0642(15) 0.0498(12) 0.0046(12) 0.0050(11) 0.0052(12)
  C6B 0.0760(17) 0.0798(18) 0.0665(16) 0.0104(15) -0.0043(14) -0.0036(14)
  C5B 0.087(2) 0.0775(18) 0.0717(16) 0.0245(15) 0.0007(15) -0.0052(16)
  C4B 0.0863(18) 0.0658(15) 0.0520(12) 0.0072(13) 0.0056(13) -0.0014(12)
  C3B 0.087(2) 0.084(2) 0.0780(18) 0.0120(16) -0.0171(16) -0.0096(17)
  C2B 0.0855(19) 0.0783(19) 0.0759(18) 0.0250(16) -0.0125(15) -0.0083(16)
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
  Br1 C4B . 1.906(3) yes
  N1 C6 . 1.455(4) yes
  N1 C2 . 1.465(3) yes
  N1 C1' . 1.466(3) yes
  C2 C3 . 1.523(4) ?
  C2 H2A . 0.9700 ?
  C2 H2B . 0.9700 ?
  C3 C3' . 1.500(5) ?
  C3 C4 . 1.536(4) ?
  C3 H3A . 0.9800 ?
  C3' H3'A . 0.9600 ?
  C3' H3'B . 0.9600 ?
  C3' H3'C . 0.9600 ?
  C4 N7 . 1.475(3) yes
  C4 C5 . 1.515(4) ?
  C4 H4A . 0.9800 ?
  C5 C6 . 1.527(4) ?
  C5 H5A . 0.9700 ?
  C5 H5B . 0.9700 ?
  C6 H6A . 0.9700 ?
  C6 H6B . 0.9700 ?
  N7 C8 . 1.368(3) yes
  N7 C1A . 1.442(3) yes
  C8 O8 . 1.224(3) ?
  C8 C9 . 1.491(4) ?
  C9 C10 . 1.300(4) yes
  C9 H9 . 0.9300 ?
  C10 H10A . 0.9300 ?
  C10 H10B . 0.9300 ?
  C1A C6A . 1.375(4) ?
  C1A C2A . 1.396(4) ?
  C2A C3A . 1.378(5) ?
  C2A H2AA . 0.9300 ?
  C3A C4A . 1.372(6) ?
  C3A H3AA . 0.9300 ?
  C4A C5A . 1.370(6) ?
  C4A H4AA . 0.9300 ?
  C5A C6A . 1.383(4) ?
  C5A H5AA . 0.9300 ?
  C6A H6AA . 0.9300 ?
  C1' C2' . 1.528(4) ?
  C1' H1'A . 0.9700 ?
  C1' H1'B . 0.9700 ?
  C2' O2' . 1.421(4) yes
  C2' C1B . 1.511(4) ?
  C2' H2'A . 0.9800 ?
  O2' H2' . 0.81(4) ?
  C1B C6B . 1.370(4) ?
  C1B C2B . 1.377(4) ?
  C6B C5B . 1.388(5) ?
  C6B H6BA . 0.9300 ?
  C5B C4B . 1.361(5) ?
  C5B H5BA . 0.9300 ?
  C4B C3B . 1.364(4) ?
  C3B C2B . 1.388(5) ?
  C3B H3BA . 0.9300 ?
  C2B H2BA . 0.9300 ?