#------------------------------------------------------------------------------
#$Date: 2008-01-26 13:05:32 +0000 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008311.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_2008311
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_journal_page_first  654
_journal_page_last  656
_publ_section_title
;
1-Chloro-2,4-dimorpholino-5-nitrobenzene
;
loop_
_publ_author_name
  "Zucco, C\'esar"
  'Neves, Ademir'
  'Vencato, Ivo'
  'Szpoganicz, Bruno'
  'Bertoldi, Fabiano C.'
_chemical_formula_moiety  'C14 H18 Cl N3 O4'
_chemical_formula_sum  'C14 H18 Cl N3 O4'
_chemical_formula_weight  327.76
_chemical_melting_point  '446-448'
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'C 2/c'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y, -z+1/2'
  'x+1/2, y+1/2, z'
  '-x+1/2, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x, -y, z-1/2'
  '-x+1/2, -y+1/2, -z'
  'x+1/2, -y+1/2, z-1/2'
_cell_length_a  22.997(5)
_cell_length_b  8.069(2)
_cell_length_c  20.001(4)
_cell_angle_alpha  90.00
_cell_angle_beta  125.00(3)
_cell_angle_gamma  90.00
_cell_volume  3040.2(12)
_cell_formula_units_Z  8
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.432
_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
  Cl 0.15081(4) 0.05925(10) 0.38101(5) 0.0554(2) Uani d . 1 . . Cl
  O1 -0.25118(9) -0.0655(2) 0.32608(11) 0.0459(5) Uani d . 1 . . O
  O2 0.16220(11) -0.5551(2) 0.47285(13) 0.0579(5) Uani d . 1 . . O
  O3 -0.06423(12) 0.4367(3) 0.28079(14) 0.0652(6) Uani d . 1 . . O
  O4 -0.09679(13) 0.3835(3) 0.35911(14) 0.0634(6) Uani d . 1 . . O
  N1 -0.11667(10) 0.0347(2) 0.36372(11) 0.0317(4) Uani d . 1 . . N
  N2 0.09947(10) -0.2358(2) 0.42920(12) 0.0364(5) Uani d . 1 . . N
  N3 -0.06845(10) 0.3455(2) 0.32643(12) 0.0358(5) Uani d . 1 . . N
  C1 -0.18293(12) 0.0612(3) 0.28189(14) 0.0402(6) Uani d . 1 . . C
  H1A -0.1907 -0.0312 0.2466 0.060 Uiso calc R 1 . . H
  H1B -0.1789 0.1614 0.2580 0.060 Uiso calc R 1 . . H
  C2 -0.24482(13) 0.0761(3) 0.28852(17) 0.0469(6) Uani d . 1 . . C
  H2A -0.2386 0.1739 0.3202 0.070 Uiso calc R 1 . . H
  H2B -0.2882 0.0899 0.2344 0.070 Uiso calc R 1 . . H
  C3 -0.18823(13) -0.0833(3) 0.40638(15) 0.0411(6) Uani d . 1 . . C
  H3A -0.1930 -0.1778 0.4328 0.062 Uiso calc R 1 . . H
  H3B -0.1815 0.0148 0.4382 0.062 Uiso calc R 1 . . H
  C4 -0.12422(12) -0.1075(3) 0.40373(15) 0.0355(5) Uani d . 1 . . C
  H4A -0.0818 -0.1188 0.4588 0.053 Uiso calc R 1 . . H
  H4B -0.1299 -0.2081 0.3740 0.053 Uiso calc R 1 . . H
  C5 -0.05375(11) 0.0420(3) 0.36762(13) 0.0306(5) Uani d . 1 . . C
  C6 -0.03242(12) 0.1830(3) 0.34536(13) 0.0335(5) Uani d . 1 . . C
  C7 0.02870(12) 0.1820(3) 0.34670(13) 0.0357(5) Uani d . 1 . . C
  H7 0.0408 0.2757 0.3301 0.043 Uiso calc R 1 . . H
  C8 0.07133(12) 0.0446(3) 0.37214(14) 0.0364(5) Uani d . 1 . . C
  C9 0.05403(12) -0.0982(3) 0.39710(13) 0.0325(5) Uani d . 1 . . C
  C10 -0.00883(12) -0.0946(3) 0.39247(14) 0.0335(5) Uani d . 1 . . C
  H10 -0.0217 -0.1901 0.4070 0.040 Uiso calc R 1 . . H
  C11 0.09202(15) -0.3459(3) 0.48193(17) 0.0448(6) Uani d . 1 . . C
  H11A 0.0491 -0.4115 0.4493 0.067 Uiso calc R 1 . . H
  H11B 0.0886 -0.2811 0.5204 0.067 Uiso calc R 1 . . H
  C12 0.15584(17) -0.4580(4) 0.52726(19) 0.0538(7) Uani d . 1 . . C
  H12A 0.1983 -0.3915 0.5608 0.081 Uiso calc R 1 . . H
  H12B 0.1517 -0.5304 0.5630 0.081 Uiso calc R 1 . . H
  C13 0.16922(15) -0.4511(4) 0.42062(19) 0.0541(7) Uani d . 1 . . C
  H13A 0.1727 -0.5193 0.3831 0.081 Uiso calc R 1 . . H
  H13B 0.2127 -0.3875 0.4531 0.081 Uiso calc R 1 . . H
  C14 0.10705(14) -0.3332(4) 0.37220(16) 0.0457(6) Uani d . 1 . . C
  H14A 0.1151 -0.2595 0.3399 0.069 Uiso calc R 1 . . H
  H14B 0.0639 -0.3954 0.3353 0.069 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 0.0465(4) 0.0647(5) 0.0716(5) 0.0012(3) 0.0436(4) 0.0085(4)
  O1 0.0317(9) 0.0514(11) 0.0523(11) -0.0052(8) 0.0228(8) 0.0005(9)
  O2 0.0641(13) 0.0406(11) 0.0774(14) 0.0121(9) 0.0456(12) -0.0006(10)
  O3 0.0708(14) 0.0560(13) 0.0834(15) 0.0163(11) 0.0528(13) 0.0344(12)
  O4 0.0902(16) 0.0469(12) 0.0777(15) 0.0204(11) 0.0625(14) 0.0144(10)
  N1 0.0287(9) 0.0331(11) 0.0340(10) 0.0010(8) 0.0184(8) 0.0044(8)
  N2 0.0410(11) 0.0369(11) 0.0395(11) 0.0056(9) 0.0279(9) -0.0007(9)
  N3 0.0374(11) 0.0320(11) 0.0387(11) -0.0013(8) 0.0223(9) 0.0058(9)
  C1 0.0347(13) 0.0447(14) 0.0353(12) -0.0009(11) 0.0167(11) 0.0034(11)
  C2 0.0307(13) 0.0506(16) 0.0490(15) 0.0031(11) 0.0167(12) 0.0077(13)
  C3 0.0379(13) 0.0452(14) 0.0462(14) -0.0002(11) 0.0276(12) 0.0044(12)
  C4 0.0361(12) 0.0341(13) 0.0409(13) 0.0002(10) 0.0248(11) 0.0045(10)
  C5 0.0289(11) 0.0342(12) 0.0299(11) -0.0012(9) 0.0175(10) -0.0009(9)
  C6 0.0344(12) 0.0336(13) 0.0298(11) -0.0009(10) 0.0168(10) 0.0017(10)
  C7 0.0381(13) 0.0388(13) 0.0324(12) -0.0023(11) 0.0215(11) 0.0046(10)
  C8 0.0332(12) 0.0460(15) 0.0349(12) -0.0020(11) 0.0223(11) 0.0001(11)
  C9 0.0347(12) 0.0350(13) 0.0304(11) 0.0009(10) 0.0201(10) -0.0017(10)
  C10 0.0355(12) 0.0314(12) 0.0371(12) -0.0010(10) 0.0227(10) 0.0015(10)
  C11 0.0569(16) 0.0373(14) 0.0546(16) 0.0061(12) 0.0404(14) 0.0033(12)
  C12 0.0662(18) 0.0423(15) 0.0613(17) 0.0189(14) 0.0413(16) 0.0099(13)
  C13 0.0464(16) 0.0571(18) 0.0653(18) 0.0079(13) 0.0359(15) -0.0122(15)
  C14 0.0471(14) 0.0531(16) 0.0460(14) 0.0013(12) 0.0320(13) -0.0109(13)
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 C8 . 1.736(2) yes
  O1 C2 . 1.420(3) no
  O1 C3 . 1.424(3) no
  O2 C12 . 1.415(3) no
  O2 C13 . 1.419(4) no
  O3 N3 . 1.219(3) yes
  O4 N3 . 1.198(3) yes
  N1 C5 . 1.405(3) yes
  N1 C4 . 1.465(3) yes
  N1 C1 . 1.478(3) yes
  N2 C9 . 1.403(3) yes
  N2 C11 . 1.462(3) yes
  N2 C14 . 1.475(3) yes
  N3 C6 . 1.480(3) yes
  C1 C2 . 1.508(3) no
  C3 C4 . 1.516(3) no
  C5 C10 . 1.393(3) no
  C5 C6 . 1.408(3) no
  C6 C7 . 1.390(3) no
  C7 C8 . 1.370(3) no
  C8 C9 . 1.401(3) no
  C9 C10 . 1.395(3) no
  C11 C12 . 1.506(4) no
  C13 C14 . 1.516(4) no