#------------------------------------------------------------------------------
#$Date: 2008-01-14 00:15:36 +0200 (Mon, 14 Jan 2008) $
#$Revision: 14 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2012387.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_2012387
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2001
_journal_volume  57
_journal_page_first  1450
_journal_page_last  1453
_publ_section_title
;
Morpholinium 2-chloro-4-nitrobenzoate, 2-chloro-5-nitrobenzoate
and 4-chloro-3-nitrobenzoate
;
loop_
_publ_author_name
  'Ishida, Hiroyuki'
  'Rahman, Bilkish'
  'Kashino,Setsuo'
_chemical_formula_moiety  'C4 H10 N O 1+, C7 H3 Cl N O4 1-'
_chemical_formula_sum  'C11 H13 Cl N2 O5'
_chemical_formula_iupac  'C4 H10 N O 1+, C7 H3 Cl N O4 1-'
_chemical_formula_weight  288.69
_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'
  '1/2-x,  -y,1/2+z'
  '1/2+x,1/2-y,  -z'
  '  -x,1/2+y,1/2-z'
_cell_length_a  10.304(2)
_cell_length_b  19.557(6)
_cell_length_c  6.4387(13)
_cell_angle_alpha  90
_cell_angle_beta  90
_cell_angle_gamma  90
_cell_volume  1297.5(5)
_cell_formula_units_Z  4
_cell_measurement_temperature  298
_exptl_crystal_density_diffrn  1.478
_diffrn_ambient_temperature  298
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
  Cl  .92033(9)  .26987(5) 1.07561(13)  .0527(3) Uani d . 1 . . Cl
  O1  .7367(2)  .42775(11)  .8920(4)  .0563(7) Uani d . 1 . . O
  O2  .6418(2)  .35904(11) 1.1175(4)  .0533(7) Uani d . 1 . . O
  O3  .8873(2)  .10450(12)  .4440(4)  .0564(7) Uani d . 1 . . O
  O4  .7277(3)  .13867(12)  .2498(4)  .0608(8) Uani d . 1 . . O
  O5 1.1351(2)  .45873(13)  .3723(3)  .0529(7) Uani d . 1 . . O
  N1  .7982(3)  .14421(14)  .4035(5)  .0438(7) Uani d . 1 . . N
  N2  .8939(2)  .46701(12)  .5821(4)  .0379(6) Uani d . 1 . . N
  C1  .7295(3)  .30998(15)  .8115(4)  .0312(8) Uani d . 1 . . C
  C2  .8235(3)  .26118(16)  .8542(4)  .0334(8) Uani d . 1 . . C
  C3  .8469(3)  .20654(15)  .7258(5)  .0354(8) Uani d . 1 . . C
  C4  .7744(3)  .20165(15)  .5466(5)  .0347(8) Uani d . 1 . . C
  C5  .6818(3)  .24974(19)  .4936(5)  .0402(8) Uani d . 1 . . C
  C6  .6616(3)  .30375(16)  .6263(5)  .0389(8) Uani d . 1 . . C
  C7  .7010(3)  .36942(16)  .9559(5)  .0343(8) Uani d . 1 . . C
  C8  .9174(3)  .41577(16)  .4179(5)  .0456(8) Uani d . 1 . . C
  C9 1.0180(4)  .4435(2)  .2674(5)  .0544(11) Uani d . 1 . . C
  C10 1.1129(3)  .51107(19)  .5230(5)  .0527(10) Uani d . 1 . . C
  C11 1.0167(3)  .48916(19)  .6842(4)  .0452(10) Uani d . 1 . . C
  H1  .9094  .1740  .7585  .042 Uiso calc R 1 . . H
  H2  .6345  .2457  .3712  .048 Uiso calc R 1 . . H
  H3  .6008  .3370  .5912  .047 Uiso calc R 1 . . H
  H4  .8410  .4493  .6773  .057 Uiso calc R 1 . . H
  H5  .8548  .5033  .5269  .057 Uiso calc R 1 . . H
  H6  .8372  .4062  .3446  .055 Uiso calc R 1 . . H
  H7  .9483  .3735  .4794  .055 Uiso calc R 1 . . H
  H8 1.0346  .4099  .1598  .065 Uiso calc R 1 . . H
  H9  .9849  .4845  .2016  .065 Uiso calc R 1 . . H
  H10 1.0811  .5518  .4536  .063 Uiso calc R 1 . . H
  H11 1.1944  .5225  .5901  .063 Uiso calc R 1 . . H
  H12 1.0522  .4517  .7649  .054 Uiso calc R 1 . . H
  H13  .9991  .5269  .7779  .054 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
  Cl  .0537(5)  .0565(6)  .0478(5)  .0121(5)  -.0151(5)  -.0085(5)
  O1  .0744(17)  .0293(13)  .0652(16)  -.0018(13)  .0380(15)  -.0009(13)
  O2  .0655(17)  .0484(15)  .0460(15)  -.0015(13)  .0206(14)  .0016(12)
  O3  .0496(16)  .0448(15)  .0748(17)  .0084(13)  .0070(15)  -.0168(14)
  O4  .0779(19)  .0534(17)  .0512(15)  -.0068(15)  -.0110(17)  -.0165(13)
  O5  .0399(14)  .0707(19)  .0482(15)  -.0027(13)  .0086(12)  .0011(14)
  N1  .0463(18)  .0379(18)  .0473(18)  -.0112(15)  .0133(18)  -.0075(16)
  N2  .0385(15)  .0374(15)  .0377(14)  .0023(12)  .0026(14)  .0060(14)
  C1  .0290(17)  .0276(18)  .0368(18)  .0002(15)  .0049(15)  .0029(14)
  C2  .0335(17)  .0354(19)  .0312(16)  -.0033(16)  .0021(14)  .0026(15)
  C3  .0347(18)  .0318(19)  .0396(18)  .0034(15)  .0024(17)  .0005(15)
  C4  .0368(17)  .0309(18)  .0364(18)  -.0022(15)  .0074(17)  -.0028(15)
  C5  .0394(19)  .045(2)  .0358(17)  -.0006(16)  -.0063(14)  .0000(14)
  C6  .0365(18)  .037(2)  .043(2)  .0073(16)  -.0022(18)  .0048(16)
  C7  .0333(17)  .0306(18)  .039(2)  .0036(15)  .0011(17)  .0012(16)
  C8  .048(2)  .0439(19)  .0448(19)  -.0063(18)  .006(2)  -.0027(19)
  C9  .066(3)  .062(3)  .036(2)  -.002(2)  .013(2)  -.005(2)
  C10  .041(2)  .059(3)  .058(2)  -.0123(19)  -.0015(18)  -.0005(19)
  C11  .054(2)  .049(2)  .0324(19)  .0052(18)  -.0076(18)  -.0005(17)
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
  Cl C2 . 1.748(3) yes
  O1 C7 . 1.267(3) yes
  O2 C7 . 1.223(4) yes
  O3 N1 . 1.230(3) yes
  O4 N1 . 1.232(3) yes
  N1 C4 . 1.474(4) no
  C1 C2 . 1.387(4) no
  C1 C6 . 1.388(4) no
  C1 C7 . 1.517(4) no
  C2 C3 . 1.372(4) no
  C3 C4 . 1.378(4) no
  C3 H1 .  .93 ?
  C4 C5 . 1.382(4) no
  C5 C6 . 1.375(4) no
  C5 H2 .  .93 ?
  C6 H3 .  .93 ?
  O5 C9 . 1.414(4) no
  O5 C10 . 1.429(4) no
  N2 C8 . 1.477(4) no
  N2 C11 . 1.490(4) no
  N2 H4 .  .89 ?
  N2 H5 .  .89 ?
  C8 C9 . 1.519(4) no
  C8 H6 .  .97 ?
  C8 H7 .  .97 ?
  C9 H8 .  .97 ?
  C9 H9 .  .97 ?
  C10 C11 . 1.499(4) no
  C10 H10 .  .97 ?
  C10 H11 .  .97 ?
  C11 H12 .  .97 ?
  C11 H13 .  .97 ?