#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2012273.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_2012273
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2001
_journal_volume  57
_journal_page_first  1189
_journal_page_last  1191
_publ_section_title
;
Azole. 47. \"Uber 3-Thiomorpholino- und 3-(N-Methylpiperazino)-5-nitroindazole
;
loop_
_publ_author_name
  'Gzella, Andrzej'
  'Wrzeciono, Urszula'
_chemical_formula_moiety  'C11 H12 N4 O2 S'
_chemical_formula_sum  'C11 H12 N4 O2 S'
_chemical_formula_weight  264.31
_symmetry_cell_setting  Monoclinic
_symmetry_space_group_name_H-M  'P 21/c'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x, -y-1/2, z-1/2'
_cell_length_a  4.3897(8)
_cell_length_b  10.4102(10)
_cell_length_c  25.829(3)
_cell_angle_alpha  90
_cell_angle_beta  91.166(12)
_cell_angle_gamma  90
_cell_volume  1180.1(3)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.488
_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  .2350(5)  .39993(19)  .01773(8)  .0452(5) Uani d . 1 . . N
  H1A  .144(7)  .416(3)  -.0115(11)  .060(8) Uiso d . 1 . . H
  N2  .1906(4)  .49003(18)  .05557(7)  .0421(4) Uani d . 1 . . N
  C3  .3505(5)  .4511(2)  .09667(8)  .0362(5) Uani d . 1 . . C
  C4  .6950(5)  .2481(2)  .11285(8)  .0379(5) Uani d . 1 . . C
  H4  .7552  .2635  .1470  .045 Uiso calc . 1 . . H
  C5  .7940(5)  .1419(2)  .08615(8)  .0409(5) Uani d . 1 . . C
  C6  .7094(5)  .1156(2)  .03465(9)  .0452(5) Uani d . 1 . . C
  H6  .7835  .0423  .0186  .054 Uiso calc . 1 . . H
  C7  .5206(6)  .1960(2)  .00787(8)  .0444(5) Uani d . 1 . . C
  H7  .4635  .1797  -.0264  .053 Uiso calc . 1 . . H
  C8  .4159(5)  .3043(2)  .03411(8)  .0384(5) Uani d . 1 . . C
  C9  .4997(5)  .33121(19)  .08587(8)  .0348(4) Uani d . 1 . . C
  N10  .3739(4)  .52494(17)  .14136(7)  .0381(4) Uani d . 1 . . N
  C11  .2603(6)  .4597(2)  .18796(8)  .0438(5) Uani d . 1 . . C
  H11A  .3349  .3720  .1887  .053 Uiso calc . 1 . . H
  H11B  .0395  .4567  .1861  .053 Uiso calc . 1 . . H
  C12  .3607(6)  .5271(2)  .23732(9)  .0508(6) Uani d . 1 . . C
  H12A  .5815  .5293  .2393  .061 Uiso calc . 1 . . H
  H12B  .2897  .4788  .2668  .061 Uiso calc . 1 . . H
  S13  .21585(15)  .68925(6)  .24065(2)  .0528(2) Uani d . 1 . . S
  C14  .3614(6)  .7410(2)  .17972(10)  .0523(6) Uani d . 1 . . C
  H14A  .2948  .8284  .1730  .063 Uiso calc . 1 . . H
  H14B  .5822  .7411  .1817  .063 Uiso calc . 1 . . H
  C15  .2576(6)  .6564(2)  .13526(9)  .0481(6) Uani d . 1 . . C
  H15A  .0367  .6546  .1336  .058 Uiso calc . 1 . . H
  H15B  .3291  .6922  .1030  .058 Uiso calc . 1 . . H
  N16  .9967(5)  .0516(2)  .11267(8)  .0544(5) Uani d . 1 . . N
  O17 1.0914(5)  .0766(2)  .15609(8)  .0709(6) Uani d . 1 . . O
  O18 1.0684(7)  -.0459(2)  .08947(9)  .0947(9) 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  .0451(12)  .0511(11)  .0391(10)  .0083(9)  -.0064(8)  -.0038(8)
  N2  .0374(11)  .0473(10)  .0415(10)  .0078(8)  -.0026(8)  -.0028(8)
  C3  .0280(11)  .0407(11)  .0399(10)  .0028(8)  .0017(8)  -.0005(8)
  C4  .0318(12)  .0422(11)  .0397(10)  .0011(8)  .0014(8)  -.0020(8)
  C5  .0343(12)  .0400(11)  .0485(12)  .0048(9)  .0045(9)  .0008(9)
  C6  .0428(14)  .0416(12)  .0515(13)  .0044(9)  .0092(10)  -.0077(9)
  C7  .0452(14)  .0485(12)  .0395(11)  .0001(10)  .0018(9)  -.0079(9)
  C8  .0306(12)  .0435(11)  .0410(11)  -.0010(8)  .0003(8)  -.0016(8)
  C9  .0264(10)  .0388(10)  .0394(10)  .0007(8)  .0036(8)  -.0032(8)
  N10  .0370(10)  .0384(9)  .0391(9)  .0059(7)  .0014(7)  -.0021(7)
  C11  .0454(14)  .0442(12)  .0419(11)  .0028(10)  .0060(9)  .0000(9)
  C12  .0577(17)  .0538(13)  .0410(12)  .0110(11)  .0007(10)  -.0011(10)
  S13  .0537(4)  .0569(4)  .0479(4)  .0097(3)  .0017(3)  -.0127(3)
  C14  .0563(16)  .0439(12)  .0566(14)  .0075(10)  .0011(11)  -.0063(10)
  C15  .0574(16)  .0432(12)  .0437(12)  .0128(10)  -.0005(10)  -.0009(9)
  N16  .0559(14)  .0524(12)  .0552(12)  .0179(10)  .0063(10)  .0015(9)
  O17  .0765(15)  .0763(13)  .0594(12)  .0331(11)  -.0106(10)  -.0007(10)
  O18  .134(2)  .0702(14)  .0790(14)  .0584(15)  -.0100(14)  -.0143(11)
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 C8 . 1.337(3) ?
  N1 N2 . 1.371(3) ?
  N1 H1A .  .86(3) ?
  N2 C3 . 1.324(3) ?
  C3 N10 . 1.389(3) ?
  C3 C9 . 1.440(3) ?
  C4 C5 . 1.378(3) ?
  C4 C9 . 1.395(3) ?
  C4 H4 .  .9300 ?
  C5 C6 . 1.400(3) ?
  C5 N16 . 1.456(3) ?
  C6 C7 . 1.357(3) ?
  C6 H6 .  .9300 ?
  C7 C8 . 1.398(3) ?
  C7 H7 .  .9300 ?
  C8 C9 . 1.408(3) ?
  N10 C15 . 1.469(3) ?
  N10 C11 . 1.477(3) ?
  C11 C12 . 1.513(3) ?
  C11 H11A .  .9700 ?
  C11 H11B .  .9700 ?
  C12 S13 . 1.806(3) ?
  C12 H12A .  .9700 ?
  C12 H12B .  .9700 ?
  S13 C14 . 1.793(3) ?
  C14 C15 . 1.510(3) ?
  C14 H14A .  .9700 ?
  C14 H14B .  .9700 ?
  C15 H15A .  .9700 ?
  C15 H15B .  .9700 ?
  N16 O17 . 1.216(3) ?
  N16 O18 . 1.223(3) ?