#------------------------------------------------------------------------------
#$Date: 2011-09-17 23:27:16 +0300 (Sat, 17 Sep 2011) $
#$Revision: 26029 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2011736.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_2011736
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2001
_journal_volume  57
_journal_page_first  66
_journal_page_last  67
_publ_section_title
;
(--)-Argemonine hemihydrate
;
_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
  'Ne\<cas, Marek'
  "Dost\'al, Ji\<r\'i"
  "Slav\'ik, Ji\<r\'i"
_chemical_name_common  '(-)-Argemonine hemihydrate'
_chemical_formula_moiety  'C21 H25 N O4, 0.5H2 O'
_chemical_formula_sum            'C21 H26 N O4.5'
_[local]_cod_chemical_formula_sum_orig 'C21 H26 N1 O4.5'
_chemical_formula_iupac  'C21 H25 N O4, 0.5H2 O'
_chemical_formula_weight  364.43
_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  18.169(4)
_cell_length_b  9.801(2)
_cell_length_c  12.726(3)
_cell_angle_alpha  90.00
_cell_angle_beta  126.96(3)
_cell_angle_gamma  90.00
_cell_volume  1810.8(7)
_cell_formula_units_Z  4
_cell_measurement_temperature  130(2)
_exptl_crystal_density_diffrn  1.337
_diffrn_ambient_temperature  130(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
  O18  .20462(7)  -.02808(11)  .71574(10)  .0185(2) Uani d . 1 . . O
  O19  .11674(7)  .16177(13)  .54123(11)  .0231(2) Uani d . 1 . . O
  O20  .59998(8)  .67489(12)  .89583(11)  .0222(2) Uani d . 1 . . O
  O21  .64642(8)  .55233(12) 1.11413(11)  .0241(2) Uani d . 1 . . O
  N1  .50822(8)  .09674(14)  .66303(12)  .0167(2) Uani d . 1 . . N
  C1  .34395(9)  .00897(14)  .73301(13)  .0147(3) Uani d . 1 . . C
  H1  .3760  -.0616  .7963  .018 Uiso calc R 1 . . H
  C2  .25372(9)  .03771(15)  .68216(13)  .0153(3) Uani d . 1 . . C
  C3  .20607(9)  .14204(15)  .58740(13)  .0170(3) Uani d . 1 . . C
  C4  .25100(9)  .21543(16)  .54884(13)  .0172(3) Uani d . 1 . . C
  H4  .2192  .2864  .4859  .021 Uiso calc R 1 . . H
  C4A  .34288(10)  .18693(14)  .60110(13)  .0159(3) Uani d . 1 . . C
  C5  .38981(10)  .26917(16)  .55722(13)  .0179(3) Uani d . 1 . . C
  H5A  .3774  .3674  .5580  .021 Uiso calc R 1 . . H
  H5B  .3645  .2437  .4660  .021 Uiso calc R 1 . . H
  C6  .49433(10)  .24432(14)  .64784(13)  .0157(3) Uani d . 1 . . C
  H6  .5207  .2798  .6032  .019 Uiso calc R 1 . . H
  C6A  .53892(9)  .32075(15)  .77685(13)  .0151(3) Uani d . 1 . . C
  C7  .55162(10)  .46154(15)  .77932(14)  .0168(3) Uani d . 1 . . C
  H7  .5348  .5069  .7018  .020 Uiso calc R 1 . . H
  C8  .58810(10)  .53527(15)  .89255(15)  .0177(3) Uani d . 1 . . C
  C9  .61269(9)  .46963(16) 1.00783(14)  .0176(3) Uani d . 1 . . C
  C10  .60070(9)  .33018(15) 1.00613(14)  .0165(3) Uani d . 1 . . C
  H10  .6173  .2850 1.0836  .020 Uiso calc R 1 . . H
  C10A  .56435(9)  .25494(14)  .89111(13)  .0142(3) Uani d . 1 . . C
  C11  .55449(9)  .10271(15)  .89139(13)  .0152(3) Uani d . 1 . . C
  H11A  .5317  .0791  .9428  .018 Uiso calc R 1 . . H
  H11B  .6156  .0594  .9345  .018 Uiso calc R 1 . . H
  C12  .48756(9)  .04657(15)  .75113(13)  .0148(3) Uani d . 1 . . C
  H12  .4931  -.0551  .7553  .018 Uiso calc R 1 . . H
  C12A  .38865(9)  .08291(14)  .69218(12)  .0144(3) Uani d . 1 . . C
  C13  .25171(10)  -.13501(17)  .80910(15)  .0209(3) Uani d . 1 . . C
  H13A  .2687  -.2061  .7731  .031 Uiso calc R 1 . . H
  H13B  .2114  -.1741  .8285  .031 Uiso calc R 1 . . H
  H13C  .3075  -.0987  .8901  .031 Uiso calc R 1 . . H
  C14  .06546(10)  .25843(18)  .43721(15)  .0254(3) Uani d . 1 . . C
  H14A  .0920  .3495  .4696  .038 Uiso calc R 1 . . H
  H14B  .0012  .2586  .4058  .038 Uiso calc R 1 . . H
  H14C  .0680  .2335  .3648  .038 Uiso calc R 1 . . H
  C15  .67676(11)  .71114(17)  .89810(16)  .0238(3) Uani d . 1 . . C
  H15A  .7327  .6694  .9748  .036 Uiso calc R 1 . . H
  H15B  .6837  .8106  .9034  .036 Uiso calc R 1 . . H
  H15C  .6668  .6784  .8176  .036 Uiso calc R 1 . . H
  C16  .66980(13)  .4889(2) 1.23151(16)  .0303(4) Uani d . 1 . . C
  H16A  .6149  .4459 1.2145  .045 Uiso calc R 1 . . H
  H16B  .6934  .5579 1.3006  .045 Uiso calc R 1 . . H
  H16C  .7172  .4195 1.2601  .045 Uiso calc R 1 . . H
  C17  .59854(10)  .05447(16)  .70245(16)  .0212(3) Uani d . 1 . . C
  H17A  .6058  .0826  .6352  .032 Uiso calc R 1 . . H
  H17B  .6040  -.0450  .7121  .032 Uiso calc R 1 . . H
  H17C  .6466  .0974  .7865  .032 Uiso calc R 1 . . H
  O30  .5000  .8061(2) 1.0000  .0331(4) Uani d S 1 . . O
  H30A  .533(2)  .757(4)  .983(3)  .084(11) Uiso d . 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
  O18  .0174(4)  .0170(5)  .0222(5)  .0010(4)  .0125(4)  .0032(4)
  O19  .0159(5)  .0238(6)  .0248(5)  .0053(4)  .0097(4)  .0063(5)
  O20  .0298(5)  .0109(5)  .0297(5)  -.0011(4)  .0199(5)  -.0013(4)
  O21  .0338(6)  .0171(5)  .0199(5)  -.0059(5)  .0154(5)  -.0045(4)
  N1  .0209(5)  .0130(5)  .0202(5)  .0004(5)  .0144(5)  .0003(4)
  C1  .0157(6)  .0127(6)  .0135(5)  .0007(5)  .0075(5)  .0005(5)
  C2  .0171(6)  .0134(6)  .0153(6)  -.0020(5)  .0096(5)  -.0021(5)
  C3  .0154(6)  .0156(6)  .0158(6)  .0016(5)  .0073(5)  -.0009(5)
  C4  .0183(6)  .0143(6)  .0144(6)  .0022(5)  .0074(5)  .0014(5)
  C4A  .0186(6)  .0140(6)  .0136(5)  -.0004(5)  .0089(5)  -.0001(5)
  C5  .0225(6)  .0155(6)  .0159(6)  .0012(5)  .0117(5)  .0026(5)
  C6  .0219(6)  .0124(6)  .0169(6)  -.0010(5)  .0138(5)  .0004(5)
  C6A  .0167(6)  .0131(6)  .0179(6)  .0000(5)  .0116(5)  .0001(5)
  C7  .0207(6)  .0137(6)  .0192(6)  .0005(5)  .0136(6)  .0019(5)
  C8  .0204(6)  .0121(6)  .0227(7)  -.0007(5)  .0141(6)  -.0002(5)
  C9  .0177(6)  .0163(7)  .0182(6)  -.0021(5)  .0105(5)  -.0023(5)
  C10  .0167(6)  .0164(7)  .0158(6)  -.0007(5)  .0094(5)  .0011(5)
  C10A  .0143(5)  .0111(6)  .0174(6)  -.0006(5)  .0096(5)  .0000(5)
  C11  .0159(6)  .0127(6)  .0159(6)  .0003(5)  .0090(5)  .0028(5)
  C12  .0174(6)  .0111(6)  .0175(6)  .0005(5)  .0114(5)  .0013(5)
  C12A  .0167(6)  .0123(6)  .0132(6)  -.0012(5)  .0084(5)  -.0010(5)
  C13  .0184(6)  .0191(7)  .0228(7)  -.0020(6)  .0111(6)  .0052(6)
  C14  .0199(6)  .0223(7)  .0243(7)  .0065(6)  .0080(6)  .0046(6)
  C15  .0276(7)  .0150(6)  .0293(7)  -.0045(6)  .0173(6)  -.0005(6)
  C16  .0430(9)  .0274(8)  .0202(7)  -.0090(8)  .0188(7)  -.0056(7)
  C17  .0237(7)  .0185(7)  .0289(7)  .0007(6)  .0198(6)  .0012(6)
  O30  .0294(9)  .0193(8)  .0492(11)  .000  .0228(9)  .000
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
  O18 C2 . 1.3611(16) ?
  O18 C13 . 1.4211(18) ?
  O19 C3 . 1.3675(17) ?
  O19 C14 . 1.4264(19) ?
  O20 C8 . 1.3820(18) ?
  O20 C15 . 1.4230(19) ?
  O21 C9 . 1.3659(18) ?
  O21 C16 . 1.426(2) ?
  N1 C6 . 1.4610(18) ?
  N1 C12 . 1.4648(17) ?
  N1 C17 . 1.4582(18) ?
  C1 C2 . 1.3821(19) ?
  C1 C12A . 1.4008(19) ?
  C1 H1 .  .9500 ?
  C2 C3 . 1.4120(19) ?
  C3 C4 . 1.381(2) ?
  C4 C4A . 1.404(2) ?
  C4 H4 .  .9500 ?
  C4A C12A . 1.3839(19) ?
  C4A C5 . 1.5037(19) ?
  C5 C6 . 1.537(2) ?
  C5 H5A .  .9900 ?
  C5 H5B .  .9900 ?
  C6 C6A . 1.5209(19) ?
  C6 H6 . 1.0000 ?
  C6A C10A . 1.3914(19) ?
  C6A C7 . 1.3963(19) ?
  C7 C8 . 1.375(2) ?
  C7 H7 .  .9500 ?
  C8 C9 . 1.406(2) ?
  C9 C10 . 1.382(2) ?
  C10 C10A . 1.4000(19) ?
  C10 H10 .  .9500 ?
  C10A C11 . 1.5029(19) ?
  C11 C12 . 1.535(2) ?
  C11 H11A .  .9900 ?
  C11 H11B .  .9900 ?
  C12 C12A . 1.5159(18) ?
  C12 H12 . 1.0000 ?
  C13 H13A .  .9800 ?
  C13 H13B .  .9800 ?
  C13 H13C .  .9800 ?
  C14 H14A .  .9800 ?
  C14 H14B .  .9800 ?
  C14 H14C .  .9800 ?
  C15 H15A .  .9800 ?
  C15 H15B .  .9800 ?
  C15 H15C .  .9800 ?
  C16 H16A .  .9800 ?
  C16 H16B .  .9800 ?
  C16 H16C .  .9800 ?
  C17 H17A .  .9800 ?
  C17 H17B .  .9800 ?
  C17 H17C .  .9800 ?
  O30 H30A .  .90(4) ?
_cod_database_code 2011736