data_2011853
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2001
_journal_volume  57
_journal_page_first  359
_journal_page_last  362
_publ_section_title
;
trans-Dioxocyclam dihydrate (1,4,8,11-tetraazacyclotetradecane-2,9-dione
dihydrate) and its Ni^II^ complex
;
loop_
_publ_author_name
  'Hubin, Timothy J.'
  'Tyryshkin, Nickolay'
  'Alcock, Nathaniel W.'
  'Busch, Daryle H.'
_chemical_formula_moiety  'C10 H18 N4 Ni O2 , 2H2 O'
_chemical_formula_sum  'C10 H22 N4 Ni O4'
_chemical_formula_iupac  '[Ni (C10 H18 N4 O2)] , 2H2 O'
_chemical_formula_weight  321.03
_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  20.861(3)
_cell_length_b  7.3385(10)
_cell_length_c  9.6130(13)
_cell_angle_alpha  90
_cell_angle_beta  112.205(2)
_cell_angle_gamma  90
_cell_volume  1362.5(3)
_cell_formula_units_Z  4
_cell_measurement_temperature  180(2)
_exptl_crystal_density_diffrn  1.565
_diffrn_ambient_temperature  180(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
  Ni1 1/4 1/4 0  .0239(4) Uani d S 1 . . Ni
  O1 0.1331(2) 0.6724(6)  .0596(5)  .0422(12) Uani d . 1 . . O
  C1 0.2651(3) 0.5716(9)  .1724(7)  .0339(16) Uani d . 1 . . C
  H1A 0.2564 0.7034  .1518  .041 Uiso calc R 1 . . H
  H1B 0.2633 0.5444  .2717  .041 Uiso calc R 1 . . H
  N2 0.2128(2) 0.4618(7)  .0531(5)  .0296(12) Uani d . 1 . . N
  C3 0.1502(3) 0.5278(10)  .0070(7)  .0350(16) Uani d . 1 . . C
  C4 0.0935(3) 0.4286(10)  -.1181(8)  .0477(19) Uani d . 1 . . C
  H4A 0.0490 0.4529  -.1069  .057 Uiso calc R 1 . . H
  H4B 0.0903 0.4824  -.2150  .057 Uiso calc R 1 . . H
  C5 0.1009(3) 0.2303(10)  -.1273(8)  .0399(17) Uani d . 1 . . C
  H5A 0.1000 0.1740  -.0344  .048 Uiso calc R 1 . . H
  H5B 0.0606 0.1830  -.2127  .048 Uiso calc R 1 . . H
  N6 0.1635(3) 0.1744(8)  -.1461(6)  .0318(13) Uani d . 1 . . N
  H6A 0.169(3) 0.230(9)  -.220(7)  .038 Uiso d . 1 . . H
  C7 0.1670(3) -0.0209(9)  -.1706(7)  .0397(17) Uani d . 1 . . C
  H7A 0.1302 -0.0552  -.2674  .048 Uiso calc R 1 . . H
  H7B 0.1589 -0.0886  -.0896  .048 Uiso calc R 1 . . H
  O2 0.0083(2) 0.8499(6)  -.0915(5)  .0465(13) 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
  Ni1  .0207(6)  .0223(6)  .0244(6)  .0015(6)  .0037(4)  -.0033(6)
  O1  .038(3)  .031(3)  .047(3)  .014(2)  .005(2)  -.009(2)
  C1  .024(3)  .026(4)  .044(4)  .005(3)  .004(3)  -.005(3)
  N2  .025(3)  .028(3)  .031(3)  .000(2)  .005(2)  -.002(2)
  C3  .030(4)  .040(4)  .033(3)  .001(3)  .010(3)  .001(3)
  C4  .033(4)  .051(5)  .050(4)  .012(4)  .005(3)  -.011(4)
  C5  .023(3)  .036(5)  .058(4)  -.003(3)  .011(3)  -.011(4)
  N6  .026(3)  .032(3)  .033(3)  .002(2)  .006(2)  -.005(3)
  C7  .032(4)  .029(4)  .050(4)  -.007(3)  .006(3)  -.010(3)
  O2  .044(3)  .034(3)  .053(3)  .012(2)  .009(2)  .000(2)
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
  Ni1 N2 7 1.892(5) ?
  Ni1 N2 . 1.892(5) y
  Ni1 N6 7 1.902(5) ?
  Ni1 N6 . 1.902(5) y
  O1 C3 . 1.282(7) ?
  C1 C7 7 1.470(8) ?
  C1 N2 . 1.487(7) ?
  N2 C3 . 1.303(7) ?
  C3 C4 . 1.517(9) ?
  C4 C5 . 1.470(9) ?
  C5 N6 . 1.444(8) ?
  N6 C7 . 1.458(8) ?
  C7 C1 7 1.470(8) ?
  N6 H6A .  .864(10) ?