data_2011337
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2000
_journal_volume  56
_journal_page_first  1161
_journal_page_last  1163
_publ_section_title
;
Azole. 44. \"Uber Morpholinonitroimidazolderivate
;
loop_
_publ_author_name
  'Gzella, Andrzej'
  'Wrzeciono, Urszula'
  'P\"oppel, Wolfram'
_chemical_formula_moiety  'C10 H15 Cl N4 O4'
_chemical_formula_sum  'C10 H15 Cl N4 O4'
_chemical_formula_weight  290.71
_symmetry_cell_setting  Monoclinic
_symmetry_space_group_name_H-M  'P 21'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z'
_cell_length_a  9.6840(8)
_cell_length_b  5.2868(8)
_cell_length_c  12.8212(7)
_cell_angle_alpha  90.00
_cell_angle_beta  106.470(6)
_cell_angle_gamma  90.00
_cell_volume  629.48(11)
_cell_formula_units_Z  2
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.534
_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
  N1  .25344(13)  .2996(3)  .44535(10)  .0324(3) Uani d . 1 . . N
  C2  .35945(16)  .1446(4)  .49604(12)  .0364(3) Uani d . 1 . . C
  H2A  .4013  .0288  .4596  .044 Uiso calc . 1 . . H
  N3  .39995(14)  .1702(3)  .60289(11)  .0360(3) Uani d . 1 . . N
  C4  .31146(15)  .3495(3)  .62562(12)  .0316(3) Uani d . 1 . . C
  C5  .22027(15)  .4378(3)  .52711(12)  .0315(3) Uani d . 1 . . C
  C6  .17975(16)  .2867(3)  .32829(12)  .0346(3) Uani d . 1 . . C
  H6A  .0845  .3606  .3142  .042 Uiso calc . 1 . . H
  H6B  .1685  .1111  .3055  .042 Uiso calc . 1 . . H
  C7  .26426(16)  .4268(3)  .26313(12)  .0341(3) Uani d . 1 . . C
  H7A  .2771  .6024  .2885  .041 Uiso calc . 1 . . H
  C8  .1863(2)  .4274(4)  .14286(13)  .0437(4) Uani d . 1 . . C
  H8A  .2432  .5202  .1045  .052 Uiso calc . 1 . . H
  H8B  .0950  .5146  .1313  .052 Uiso calc . 1 . . H
  Cl9  .15358(5)  .11495(11)  .08745(3)  .05587(16) Uani d . 1 . . Cl
  O10  .40081(13)  .3153(3)  .28177(10)  .0419(3) Uani d . 1 . . O
  H10A  .462(3)  .395(5)  .3097(19)  .049(7) Uiso d . 1 . . H
  N11  .32214(13)  .4247(3)  .72854(10)  .0363(3) Uani d . 1 . . N
  C12  .45195(17)  .3614(3)  .81480(12)  .0362(3) Uani d . 1 . . C
  H12A  .5354  .3695  .7873  .043 Uiso calc . 1 . . H
  H12B  .4446  .1910  .8408  .043 Uiso calc . 1 . . H
  C13  .46770(18)  .5472(4)  .90583(13)  .0403(4) Uani d . 1 . . C
  H13A  .5519  .5035  .9648  .048 Uiso calc . 1 . . H
  H13B  .4828  .7148  .8803  .048 Uiso calc . 1 . . H
  O14  .34471(13)  .5516(3)  .94579(10)  .0488(3) Uani d . 1 . . O
  C15  .21984(19)  .6160(5)  .86044(15)  .0494(4) Uani d . 1 . . C
  H15A  .2313  .7843  .8340  .059 Uiso calc . 1 . . H
  H15B  .1367  .6180  .8884  .059 Uiso calc . 1 . . H
  C16  .19449(17)  .4310(4)  .76809(13)  .0417(4) Uani d . 1 . . C
  H16A  .1763  .2640  .7927  .050 Uiso calc . 1 . . H
  H16B  .1110  .4818  .7099  .050 Uiso calc . 1 . . H
  N17  .14224(13)  .6623(3)  .50655(11)  .0351(3) Uani d . 1 . . N
  O18  .11854(15)  .7774(3)  .58335(11)  .0509(3) Uani d . 1 . . O
  O19  .10343(15)  .7434(3)  .41192(11)  .0492(3) Uani d . 1 . . O
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
  N1  .0317(6)  .0353(7)  .0286(6)  .0005(5)  .0060(5)  -.0009(5)
  C2  .0366(7)  .0351(8)  .0369(8)  .0061(7)  .0092(6)  -.0013(7)
  N3  .0350(6)  .0350(8)  .0356(6)  .0068(6)  .0063(5)  .0009(6)
  C4  .0295(6)  .0318(8)  .0319(7)  .0004(6)  .0062(5)  .0002(6)
  C5  .0300(6)  .0327(8)  .0309(7)  .0022(6)  .0073(5)  .0011(6)
  C6  .0325(7)  .0407(9)  .0283(7)  -.0067(7)  .0049(5)  -.0012(6)
  C7  .0362(7)  .0340(8)  .0324(7)  -.0055(6)  .0103(6)  -.0020(6)
  C8  .0492(9)  .0483(10)  .0333(8)  -.0023(8)  .0109(6)  .0045(7)
  Cl9  .0524(3)  .0688(3)  .0433(2)  -.0123(2)  .00850(17)  -.0192(2)
  O10  .0322(6)  .0464(8)  .0471(7)  -.0075(5)  .0110(5)  -.0112(6)
  N11  .0309(6)  .0478(8)  .0290(6)  .0055(6)  .0064(5)  -.0010(6)
  C12  .0354(7)  .0393(9)  .0309(7)  .0051(6)  .0046(6)  .0025(6)
  C13  .0405(8)  .0488(10)  .0316(7)  -.0037(7)  .0102(6)  -.0026(7)
  O14  .0475(7)  .0691(9)  .0329(6)  -.0036(6)  .0164(5)  -.0027(6)
  C15  .0435(9)  .0637(12)  .0450(9)  .0055(9)  .0190(7)  -.0047(9)
  C16  .0338(7)  .0534(10)  .0389(8)  -.0010(7)  .0121(6)  .0008(8)
  N17  .0314(6)  .0319(7)  .0411(7)  .0037(6)  .0088(5)  .0047(6)
  O18  .0546(7)  .0446(8)  .0558(8)  .0154(6)  .0193(6)  -.0037(6)
  O19  .0543(7)  .0433(7)  .0473(7)  .0109(6)  .0098(5)  .0170(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
  N1 C2 . 1.330(2) yes
  N1 C5 . 1.388(2) yes
  N1 C6 . 1.4693(18) ?
  C2 N3 . 1.321(2) yes
  N3 C4 . 1.364(2) yes
  C4 N11 . 1.354(2) yes
  C4 C5 . 1.400(2) yes
  C5 N17 . 1.391(2) yes
  C6 C7 . 1.518(2) ?
  C7 O10 . 1.405(2) ?
  C7 C8 . 1.512(2) ?
  C8 Cl9 . 1.791(2) yes
  O10 H10A .  .73(3) ?
  N11 C12 . 1.4585(19) ?
  N11 C16 . 1.4634(19) ?
  C12 C13 . 1.500(2) ?
  C13 O14 . 1.424(2) ?
  O14 C15 . 1.423(2) ?
  C15 C16 . 1.501(3) ?
  N17 O18 . 1.2331(18) ?
  N17 O19 . 1.2403(18) ?