data_2012388
_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  monoclinic
_symmetry_space_group_name_H-M  'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
loop_
_symmetry_equiv_pos_as_xyz
  '  +x,  +y,  +z'
  '  -x,  +y,1/2-z'
  '  -x,  -y,  -z'
  '  +x,  -y,1/2+z'
  '1/2+x,1/2+y,  +z'
  '1/2-x,1/2+y,1/2-z'
  '1/2-x,1/2-y,  -z'
  '1/2+x,1/2-y,1/2+z'
_cell_length_a  18.680(6)
_cell_length_b  10.498(3)
_cell_length_c  13.125(3)
_cell_angle_alpha  90
_cell_angle_beta  93.35(2)
_cell_angle_gamma  90
_cell_volume  2569.5(13)
_cell_formula_units_Z  8
_cell_measurement_temperature  298
_exptl_crystal_density_diffrn  1.492
_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  .58105(4)  .37294(7)  .32979(6)  .0559(3) Uani d . 1 . . Cl
  O1  .61609(11)  .00193(18)  .36764(15)  .0556(5) Uani d . 1 . . O
  O2  .58973(9)  .14191(18)  .48707(14)  .0506(5) Uani d . 1 . . O
  O3  .92286(11)  .2335(3)  .30218(17)  .0784(8) Uani d . 1 . . O
  O4  .89280(11)  .0791(2)  .3986(2)  .0720(7) Uani d . 1 . . O
  O5  .31960(10)  .29981(19)  .43692(15)  .0550(5) Uani d . 1 . . O
  N1  .87919(12)  .1750(3)  .34898(18)  .0527(6) Uani d . 1 . . N
  N2  .44683(12)  .1719(2)  .50853(18)  .0432(6) Uani d . 1 . . N
  C1  .68165(12)  .1917(2)  .37796(17)  .0335(5) Uani d . 1 . . C
  C2  .66822(13)  .3131(2)  .33920(18)  .0377(6) Uani d . 1 . . C
  C3  .72200(16)  .3875(3)  .3022(2)  .0472(7) Uani d . 1 . . C
  C4  .79118(16)  .3433(3)  .3050(2)  .0477(7) Uani d . 1 . . C
  C5  .80519(13)  .2243(2)  .34609(18)  .0392(6) Uani d . 1 . . C
  C6  .75198(13)  .1480(2)  .38116(18)  .0371(6) Uani d . 1 . . C
  C7  .62345(12)  .1057(2)  .41338(18)  .0373(6) Uani d . 1 . . C
  C8  .41171(17)  .1445(3)  .4057(2)  .0527(7) Uani d . 1 . . C
  C9  .33271(16)  .1724(3)  .4082(2)  .0523(7) Uani d . 1 . . C
  C10  .35140(16)  .3231(3)  .5362(2)  .0524(7) Uani d . 1 . . C
  C11  .43096(15)  .3038(3)  .5412(2)  .0475(7) Uani d . 1 . . C
  H1  .7123(15)  .460(3)  .275(2)  .057(9) Uiso d . 1 . . H
  H2  .8270(15)  .390(2)  .283(2)  .048(8) Uiso d . 1 . . H
  H3  .7624(12)  .062(3)  .4072(18)  .040(7) Uiso d . 1 . . H
  H4  .4906(16)  .161(3)  .503(2)  .049(8) Uiso d . 1 . . H
  H5  .4300(17)  .108(3)  .558(3)  .080(10) Uiso d . 1 . . H
  H6  .4323(18)  .197(3)  .361(3)  .073(10) Uiso d . 1 . . H
  H7  .4214(15)  .055(3)  .387(2)  .064(9) Uiso d . 1 . . H
  H8  .3075(16)  .159(3)  .336(2)  .062(9) Uiso d . 1 . . H
  H9  .3098(14)  .117(3)  .454(2)  .051(8) Uiso d . 1 . . H
  H10  .3438(15)  .411(3)  .550(2)  .060(9) Uiso d . 1 . . H
  H11  .3310(16)  .268(3)  .584(2)  .061(9) Uiso d . 1 . . H
  H12  .4530(14)  .359(2)  .495(2)  .045(8) Uiso d . 1 . . H
  H13  .4546(16)  .311(3)  .610(2)  .064(9) 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
  Cl  .0463(4)  .0548(4)  .0658(5)  .0102(3)  -.0024(3)  .0033(4)
  O1  .0674(13)  .0458(11)  .0557(12)  -.0179(10)  .0207(10)  -.0075(9)
  O2  .0397(10)  .0620(12)  .0520(11)  -.0028(9)  .0180(9)  -.0051(9)
  O3  .0406(11)  .132(2)  .0645(13)  -.0101(13)  .0187(10)  .0137(14)
  O4  .0443(12)  .0661(15)  .1056(19)  .0073(11)  .0033(12)  .0037(14)
  O5  .0477(11)  .0564(12)  .0596(12)  .0025(10)  -.0091(9)  .0078(10)
  N1  .0351(12)  .0757(18)  .0477(14)  -.0077(12)  .0049(11)  -.0124(13)
  N2  .0307(12)  .0499(14)  .0497(13)  -.0009(10)  .0084(10)  .0079(11)
  C1  .0343(12)  .0373(13)  .0293(11)  -.0034(10)  .0042(10)  -.0035(10)
  C2  .0350(12)  .0415(14)  .0365(13)  .0023(11)  .0006(10)  -.0030(11)
  C3  .0600(18)  .0366(15)  .0451(15)  -.0056(14)  .0029(13)  .0048(13)
  C4  .0477(16)  .0530(17)  .0433(15)  -.0184(14)  .0092(13)  -.0019(13)
  C5  .0341(13)  .0498(15)  .0338(13)  -.0044(12)  .0026(10)  -.0076(12)
  C6  .0368(13)  .0413(15)  .0335(12)  -.0042(11)  .0043(10)  -.0028(11)
  C7  .0331(12)  .0429(14)  .0360(13)  -.0009(11)  .0032(10)  .0008(11)
  C8  .0596(19)  .054(2)  .0457(16)  -.0022(15)  .0125(14)  .0003(14)
  C9  .0526(17)  .0575(19)  .0457(16)  -.0119(15)  -.0055(14)  .0068(14)
  C10  .0476(17)  .0522(18)  .0571(19)  .0045(14)  .0013(15)  -.0034(16)
  C11  .0407(15)  .0492(17)  .0522(17)  -.0043(13)  -.0017(13)  .0008(14)
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 . 1.743(3) yes
  O1 C7 . 1.247(3) yes
  O2 C7 . 1.244(3) yes
  O3 N1 . 1.216(3) yes
  O4 N1 . 1.218(3) yes
  C1 C2 . 1.389(3) no
  C1 C6 . 1.390(3) no
  C1 C7 . 1.508(3) no
  C2 C3 . 1.383(4) no
  C3 C4 . 1.372(4) no
  C3 H1 .  .86(3) ?
  C4 C5 . 1.379(4) no
  C4 H2 .  .89(3) ?
  C5 C6 . 1.376(3) no
  C6 H3 .  .98(3) ?
  O5 C9 . 1.415(4) no
  O5 C10 . 1.421(3) no
  N1 C5 . 1.474(3) no
  N2 C11 . 1.484(4) no
  N2 C8 . 1.494(4) no
  N2 H4 .  .83(3) ?
  N2 H5 .  .99(4) ?
  C8 C9 . 1.507(4) no
  C8 H6 .  .91(3) ?
  C8 H7 .  .99(3) ?
  C9 H8 . 1.04(3) ?
  C9 H9 .  .96(3) ?
  C10 C11 . 1.497(4) no
  C10 H10 .  .95(3) ?
  C10 H11 .  .95(3) ?
  C11 H12 .  .95(3) ?
  C11 H13 .  .99(3) ?