data_2012190
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2001
_journal_volume  57
_journal_page_first  1084
_journal_page_last  1088
_publ_section_title
;
\p-Facial selectivities of diastereotopic ketones:
p-bromobenzoates of 4-hetero-1-decalinols.
;
loop_
_publ_author_name
  'Parvez, Masood'
  'Yadav, Veejendra K.'
  'Balamurugan, Rengarajan'
_chemical_name_common  'N-benzyl-cis-4-aza-1-decalinol p-bromobenzoate'
_chemical_formula_moiety  'C23 H26 Br N O2'
_chemical_formula_sum  'C23 H26 Br N O2'
_chemical_formula_weight  428.36
_symmetry_cell_setting  'triclinic'
_symmetry_space_group_name_H-M  'P -1'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, -z'
_cell_length_a  11.914(3)
_cell_length_b  13.144(3)
_cell_length_c  6.922(2)
_cell_angle_alpha  96.06(2)
_cell_angle_beta  106.22(2)
_cell_angle_gamma  100.42(3)
_cell_volume  1009.6(5)
_cell_formula_units_Z  2
_cell_measurement_temperature  170(2)
_exptl_crystal_density_diffrn  1.409
_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
  Br1  .42113(7)  .14473(6)  .24555(11)  .0465(2) Uani d . 1 . . Br
  O1  .6728(3)  .4668(3)  -.2993(6)  .0341(11) Uani d . 1 . . O
  O2  .7113(4)  .3176(3)  -.4277(6)  .0430(12) Uani d . 1 . . O
  N1  .8553(4)  .7240(3)  -.4752(6)  .0246(12) Uani d . 1 . . N
  C1  .7295(5)  .6837(4)  -.5911(9)  .0348(16) Uani d . 1 . . C
  H1A  .7232  .6443  -.7251  .042 Uiso calc R 1 . . H
  H1B  .6894  .7429  -.6155  .042 Uiso calc R 1 . . H
  C2  .6676(5)  .6120(4)  -.4755(9)  .0338(16) Uani d . 1 . . C
  H2A  .6676  .6529  -.3469  .041 Uiso calc R 1 . . H
  H2B  .5832  .5826  -.5587  .041 Uiso calc R 1 . . H
  C3  .7303(5)  .5240(4)  -.4280(9)  .0304(16) Uani d . 1 . . C
  H3  .7191  .4763  -.5576  .036 Uiso calc R 1 . . H
  C4  .8648(5)  .5656(4)  -.3186(8)  .0279(15) Uani d . 1 . . C
  H4  .9037  .5042  -.3122  .034 Uiso calc R 1 . . H
  C5  .8946(5)  .6231(4)  -.1002(8)  .0323(16) Uani d . 1 . . C
  H5A  .8563  .6840  -.1017  .039 Uiso calc R 1 . . H
  H5B  .8620  .5754  -.0178  .039 Uiso calc R 1 . . H
  C6 1.0306(5)  .6610(5)  -.0026(9)  .0441(18) Uani d . 1 . . C
  H6A 1.0478  .7014  .1353  .053 Uiso calc R 1 . . H
  H6B 1.0680  .5997  .0117  .053 Uiso calc R 1 . . H
  C7 1.0843(5)  .7299(5)  -.1330(9)  .0397(18) Uani d . 1 . . C
  H7A 1.0534  .7949  -.1350  .048 Uiso calc R 1 . . H
  H7B 1.1726  .7499  -.0725  .048 Uiso calc R 1 . . H
  C8 1.0528(5)  .6724(4)  -.3489(9)  .0364(16) Uani d . 1 . . C
  H8A 1.0888  .6101  -.3468  .044 Uiso calc R 1 . . H
  H8B 1.0877  .7190  -.4307  .044 Uiso calc R 1 . . H
  C9  .9177(5)  .6375(4)  -.4502(8)  .0271(15) Uani d . 1 . . C
  H9  .9026  .5957  -.5879  .032 Uiso calc R 1 . . H
  C10  .9084(5)  .8056(4)  -.5720(8)  .0291(15) Uani d . 1 . . C
  H10A  .8963  .7765  -.7160  .035 Uiso calc R 1 . . H
  H10B  .9958  .8267  -.5023  .035 Uiso calc R 1 . . H
  C11  .8556(5)  .9003(4)  -.5654(9)  .0293(15) Uani d . 1 . . C
  C12  .8504(5)  .9502(5)  -.3834(10)  .0433(18) Uani d . 1 . . C
  H12  .8808  .9241  -.2609  .052 Uiso calc R 1 . . H
  C13  .8017(6) 1.0370(5)  -.3769(12)  .057(2) Uani d . 1 . . C
  H13  .7965 1.0690  -.2510  .068 Uiso calc R 1 . . H
  C14  .7601(6) 1.0783(5)  -.5517(14)  .061(2) Uani d . 1 . . C
  H14  .7287 1.1396  -.5459  .074 Uiso calc R 1 . . H
  C15  .7647(6) 1.0300(6)  -.7330(13)  .055(2) Uani d . 1 . . C
  H15  .7348 1.0569  -.8548  .066 Uiso calc R 1 . . H
  C16  .8130(5)  .9419(5)  -.7394(10)  .0371(17) Uani d . 1 . . C
  H16  .8167  .9094  -.8661  .044 Uiso calc R 1 . . H
  C17  .6702(5)  .3632(5)  -.3126(9)  .0263(14) Uani d . 1 . . C
  C18  .6095(5)  .3139(5)  -.1750(8)  .0252(15) Uani d . 1 . . C
  C19  .5804(5)  .3723(5)  -.0246(9)  .0341(16) Uani d . 1 . . C
  H19  .5987  .4467  -.0075  .041 Uiso calc R 1 . . H
  C20  .5238(5)  .3212(5)  .1023(9)  .0407(18) Uani d . 1 . . C
  H20  .5033  .3604  .2056  .049 Uiso calc R 1 . . H
  C21  .4985(5)  .2126(5)  .0742(9)  .0337(16) Uani d . 1 . . C
  C22  .5246(5)  .1556(5)  -.0765(9)  .0367(17) Uani d . 1 . . C
  H22  .5041  .0812  -.0959  .044 Uiso calc R 1 . . H
  C23  .5807(5)  .2051(4)  -.2011(8)  .0290(15) Uani d . 1 . . C
  H23  .5996  .1648  -.3051  .035 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  .0549(5)  .0436(5)  .0430(4)  -.0009(3)  .0237(3)  .0128(3)
  O1  .037(3)  .026(3)  .050(3)  .004(2)  .028(2)  .014(2)
  O2  .053(3)  .032(3)  .055(3)  .012(2)  .032(3)  .009(2)
  N1  .016(3)  .028(3)  .032(3)  .005(2)  .009(2)  .010(2)
  C1  .023(4)  .036(4)  .047(4)  .008(3)  .009(3)  .020(3)
  C2  .017(3)  .030(4)  .052(4)  .000(3)  .009(3)  .011(3)
  C3  .030(4)  .026(4)  .040(4)  .003(3)  .017(3)  .012(3)
  C4  .028(4)  .022(3)  .041(4)  .012(3)  .015(3)  .011(3)
  C5  .039(4)  .034(4)  .031(4)  .010(3)  .017(3)  .010(3)
  C6  .045(5)  .037(4)  .047(4)  .007(4)  .010(4)  .004(3)
  C7  .022(4)  .038(4)  .055(5)  .002(3)  .008(3)  .013(4)
  C8  .025(4)  .036(4)  .055(4)  .010(3)  .016(3)  .018(4)
  C9  .026(4)  .025(4)  .031(4)  .006(3)  .011(3)  .002(3)
  C10  .030(4)  .025(4)  .038(4)  .008(3)  .014(3)  .014(3)
  C11  .027(4)  .021(4)  .043(4)  .004(3)  .015(3)  .010(3)
  C12  .045(4)  .037(4)  .059(5)  .015(4)  .030(4)  .007(4)
  C13  .059(5)  .041(5)  .091(6)  .014(4)  .056(5)  .007(5)
  C14  .045(5)  .019(5)  .137(8)  .007(4)  .053(6)  .022(5)
  C15  .036(5)  .041(5)  .095(7)  .017(4)  .022(4)  .029(5)
  C16  .028(4)  .030(4)  .053(5)  .005(3)  .010(3)  .012(4)
  C17  .019(4)  .021(4)  .038(4)  .003(3)  .009(3)  .008(3)
  C18  .019(4)  .031(4)  .026(4)  .007(3)  .006(3)  .010(3)
  C19  .033(4)  .019(4)  .042(4)  -.001(3)  .007(3)  -.005(3)
  C20  .040(4)  .040(5)  .047(4)  .000(3)  .026(4)  .009(4)
  C21  .029(4)  .041(4)  .028(4)  -.003(3)  .007(3)  .015(3)
  C22  .045(4)  .024(4)  .042(4)  .000(3)  .018(4)  .010(3)
  C23  .028(4)  .029(4)  .030(4)  .008(3)  .009(3)  .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
  Br1 C21 . 1.894(5) y
  O1 C17 . 1.348(6) y
  O1 C3 . 1.457(6) y
  O2 C17 . 1.207(6) y
  N1 C1 . 1.457(6) y
  N1 C10 . 1.464(6) y
  N1 C9 . 1.467(6) y
  C1 C2 . 1.520(6) n
  C1 H1A .  .9900 n
  C1 H1B .  .9900 n
  C2 C3 . 1.503(7) n
  C2 H2A .  .9900 n
  C2 H2B .  .9900 n
  C3 C4 . 1.536(7) n
  C3 H3 . 1.0000 n
  C4 C5 . 1.531(7) n
  C4 C9 . 1.551(7) n
  C4 H4 . 1.0000 n
  C5 C6 . 1.535(7) n
  C5 H5A .  .9900 n
  C5 H5B .  .9900 n
  C6 C7 . 1.527(7) n
  C6 H6A .  .9900 n
  C6 H6B .  .9900 n
  C7 C8 . 1.513(7) n
  C7 H7A .  .9900 n
  C7 H7B .  .9900 n
  C8 C9 . 1.526(7) n
  C8 H8A .  .9900 n
  C8 H8B .  .9900 n
  C9 H9 . 1.0000 n
  C10 C11 . 1.495(7) n
  C10 H10A .  .9900 n
  C10 H10B .  .9900 n
  C11 C12 . 1.380(7) n
  C11 C16 . 1.381(7) n
  C12 C13 . 1.373(8) n
  C12 H12 .  .9500 n
  C13 C14 . 1.379(9) n
  C13 H13 .  .9500 n
  C14 C15 . 1.365(9) n
  C14 H14 .  .9500 n
  C15 C16 . 1.385(8) n
  C15 H15 .  .9500 n
  C16 H16 .  .9500 n
  C17 C18 . 1.482(7) n
  C18 C19 . 1.387(7) n
  C18 C23 . 1.389(7) n
  C19 C20 . 1.403(7) n
  C19 H19 .  .9500 n
  C20 C21 . 1.386(7) n
  C20 H20 .  .9500 n
  C21 C22 . 1.359(7) n
  C22 C23 . 1.377(7) n
  C22 H22 .  .9500 n
  C23 H23 .  .9500 n