#------------------------------------------------------------------------------
#$Date: 2009-11-18 16:56:34 +0200 (Wed, 18 Nov 2009) $
#$Revision: 858 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2012884.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_2012884
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o503
_journal_page_last  o506
_publ_section_title
;
Two optically active isoquinoline derivatives
;
_space_group_IT_number           5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_[local]_cod_cif_authors_sg_H-M  'C 2'
loop_
_publ_author_name
  'Gzella, Andrzej'
  'Br\'ozda, Danuta'
  'Koroniak, Lukasz'
  'Rozwadowska, Maria D.'
_chemical_formula_moiety  'C16 H18 N O 1+, Br 1-, 0.5C H4 O1'
_chemical_formula_sum            'C16.5 H20 Br N O1.5'
_[local]_cod_chemical_formula_sum_orig 'C16.50 H20 Br N O1.50'
_chemical_formula_iupac  'C16 H18 N O 1+, Br 1-, 0.5C H4 O1'
_chemical_formula_weight  336.25
_symmetry_cell_setting  Monoclinic
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y, -z'
  'x+1/2, y+1/2, z'
  '-x+1/2, y+1/2, -z'
_cell_length_a  20.5882(14)
_cell_length_b  6.4413(6)
_cell_length_c  11.7354(6)
_cell_angle_alpha  90.00
_cell_angle_beta  91.004(5)
_cell_angle_gamma  90.00
_cell_volume  1556.0(2)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.435
_diffrn_ambient_temperature  293(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
  Br 0.323588(14) 0.25337(7) -0.15463(2) 0.06295(12) Uani d . 1 . . Br
  C1 0.28368(17) 0.2903(5) 0.1680(3) 0.0604(8) Uani d . 1 . . C
  H1A 0.3026 0.1649 0.1370 0.072 Uiso calc . 1 . . H
  H1B 0.2368 0.2753 0.1644 0.072 Uiso calc . 1 . . H
  N2 0.30286(13) 0.4706(4) 0.0966(2) 0.0525(6) Uani d . 1 . . N
  H2A 0.2754(17) 0.580(7) 0.107(3) 0.061(10) Uiso d . 1 . . H
  H2B 0.2984(19) 0.429(7) 0.016(4) 0.067(11) Uiso d . 1 . . H
  C3 0.37024(15) 0.5458(5) 0.1205(2) 0.0534(6) Uani d . 1 . . C
  H3 0.4001 0.4277 0.1161 0.064 Uiso calc . 1 . . H
  C4 0.37215(14) 0.6309(5) 0.2436(2) 0.0493(6) Uani d . 1 . . C
  H4 0.3419 0.7483 0.2468 0.059 Uiso calc . 1 . . H
  C5 0.36770(16) 0.4695(6) 0.4407(3) 0.0597(7) Uani d . 1 . . C
  H5 0.3965 0.5710 0.4666 0.072 Uiso calc . 1 . . H
  C6 0.34464(19) 0.3246(6) 0.5162(3) 0.0682(10) Uani d . 1 . . C
  H6 0.3588 0.3272 0.5919 0.082 Uiso calc . 1 . . H
  C7 0.30071(18) 0.1759(6) 0.4806(3) 0.0676(9) Uani d . 1 . . C
  H7 0.2845 0.0800 0.5321 0.081 Uiso calc . 1 . . H
  C8 0.28108(16) 0.1708(5) 0.3681(3) 0.0600(7) Uani d . 1 . . C
  H8 0.2513 0.0709 0.3437 0.072 Uiso calc . 1 . . H
  C9 0.30511(14) 0.3130(4) 0.2904(2) 0.0499(7) Uani d . 1 . . C
  C10 0.34859(14) 0.4670(5) 0.3258(2) 0.0491(6) Uani d . 1 . . C
  C11 0.38801(18) 0.7016(6) 0.0308(3) 0.0647(9) Uani d . 1 . . C
  H11A 0.4312 0.7559 0.0465 0.078 Uiso calc . 1 . . H
  H11B 0.3880 0.6357 -0.0435 0.078 Uiso calc . 1 . . H
  O12 0.34219(15) 0.8648(4) 0.0314(2) 0.0747(7) Uani d . 1 . . O
  H12 0.359(2) 0.920(8) -0.022(4) 0.084(14) Uiso d . 1 . . H
  C13 0.44004(14) 0.7130(5) 0.2732(2) 0.0510(7) Uani d . 1 . . C
  C14 0.49443(18) 0.5933(6) 0.2602(3) 0.0664(8) Uani d . 1 . . C
  H14 0.4903 0.4572 0.2346 0.080 Uiso calc . 1 . . H
  C15 0.55589(19) 0.6736(9) 0.2851(4) 0.0808(13) Uani d . 1 . . C
  H15 0.5924 0.5918 0.2739 0.097 Uiso calc . 1 . . H
  C16 0.5630(2) 0.8698(9) 0.3255(4) 0.0803(12) Uani d . 1 . . C
  H16 0.6042 0.9224 0.3422 0.096 Uiso calc . 1 . . H
  C17 0.5083(2) 0.9908(8) 0.3415(4) 0.0885(12) Uani d . 1 . . C
  H17 0.5125 1.1244 0.3708 0.106 Uiso calc . 1 . . H
  C18 0.44771(18) 0.9135(6) 0.3141(3) 0.0680(8) Uani d . 1 . . C
  H18 0.4113 0.9971 0.3233 0.082 Uiso calc . 1 . . H
  O19 0.5000 0.147(2) 1.0000 0.211(5) Uani d S 1 . . O
  C20 0.4793(8) 0.315(2) 0.9614(13) 0.117(4) Uani d P 0.50 . . C
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
  Br 0.07771(19) 0.06541(19) 0.04600(15) -0.00797(19) 0.00925(11) 0.00064(17)
  C1 0.0795(18) 0.056(2) 0.0457(13) -0.0045(15) -0.0041(12) 0.0025(13)
  N2 0.0694(15) 0.0497(14) 0.0383(12) 0.0023(12) -0.0028(10) -0.0003(10)
  C3 0.0625(16) 0.0552(16) 0.0427(14) 0.0047(13) 0.0033(12) 0.0001(12)
  C4 0.0551(14) 0.0528(16) 0.0402(13) 0.0048(12) 0.0015(11) -0.0014(11)
  C5 0.0672(18) 0.071(2) 0.0408(14) -0.0028(15) -0.0016(12) -0.0006(13)
  C6 0.0727(19) 0.090(3) 0.0421(15) 0.0030(17) 0.0018(13) 0.0080(14)
  C7 0.074(2) 0.077(2) 0.0527(16) 0.0012(16) 0.0091(14) 0.0180(15)
  C8 0.0648(17) 0.0600(17) 0.0553(17) -0.0001(14) 0.0017(13) 0.0055(13)
  C9 0.0572(14) 0.0486(18) 0.0439(14) 0.0058(11) 0.0022(11) 0.0009(10)
  C10 0.0541(14) 0.0538(16) 0.0396(13) 0.0094(12) 0.0022(11) 0.0008(11)
  C11 0.0749(18) 0.077(3) 0.0427(13) -0.0031(16) 0.0054(12) 0.0031(14)
  O12 0.0894(17) 0.0693(15) 0.0655(15) 0.0041(13) 0.0053(13) 0.0205(13)
  C13 0.0585(14) 0.051(2) 0.0439(12) -0.0008(12) 0.0010(10) 0.0072(12)
  C14 0.0695(19) 0.066(2) 0.0639(19) 0.0081(16) -0.0017(16) -0.0035(16)
  C15 0.0599(19) 0.112(3) 0.070(2) 0.016(2) -0.0014(17) 0.007(2)
  C16 0.068(2) 0.092(3) 0.080(3) -0.011(2) -0.0111(19) 0.006(2)
  C17 0.096(3) 0.072(2) 0.097(3) -0.017(2) -0.014(2) -0.002(2)
  C18 0.071(2) 0.057(2) 0.076(2) 0.0044(15) -0.0050(17) -0.0091(17)
  O19 0.170(8) 0.141(8) 0.324(17) 0.000 0.022(9) 0.000
  C20 0.141(11) 0.093(9) 0.118(9) 0.016(7) 0.013(7) -0.008(6)
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
  C1 N2 . 1.490(4) ?
  C1 C9 . 1.503(4) ?
  C1 H1A . 0.97 ?
  C1 H1B . 0.97 ?
  N2 C3 . 1.491(4) ?
  N2 H2A . 0.92(4) ?
  N2 H2B . 0.99(4) ?
  C3 C11 . 1.505(4) ?
  C3 C4 . 1.545(4) ?
  C3 H3 . 0.98 ?
  C4 C10 . 1.515(4) ?
  C4 C13 . 1.529(4) ?
  C4 H4 . 0.98 ?
  C5 C6 . 1.377(5) ?
  C5 C10 . 1.398(4) ?
  C5 H5 . 0.93 ?
  C6 C7 . 1.378(5) ?
  C6 H6 . 0.93 ?
  C7 C8 . 1.374(5) ?
  C7 H7 . 0.93 ?
  C8 C9 . 1.390(4) ?
  C8 H8 . 0.93 ?
  C9 C10 . 1.395(4) ?
  C11 O12 . 1.412(5) ?
  C11 H11A . 0.97 ?
  C11 H11B . 0.97 ?
  O12 H12 . 0.81(5) ?
  C13 C14 . 1.370(5) ?
  C13 C18 . 1.386(5) ?
  C14 C15 . 1.393(6) ?
  C14 H14 . 0.93 ?
  C15 C16 . 1.357(7) ?
  C15 H15 . 0.93 ?
  C16 C17 . 1.386(7) ?
  C16 H16 . 0.93 ?
  C17 C18 . 1.376(6) ?
  C17 H17 . 0.93 ?
  C18 H18 . 0.93 ?
  O19 C20 2_657 1.247(14) ?
  O19 C20 . 1.247(14) ?
  C20 C20 2_657 1.23(3) ?