data_2012616
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2002
_journal_volume  58
_journal_page_first  o226
_journal_page_last  o227
_publ_section_title
;
cis-Dioxocyclam
;
loop_
_publ_author_name
  'Mashuta, Mark S.'
  'Pimenov, Konstantin V.'
  'Grapperhaus, Craig A.'
_chemical_name_common  cis-Dioxocyclam
_chemical_formula_moiety  'C10 H20 N4 O2'
_chemical_formula_sum  'C10 H20 N4 O2'
_chemical_formula_weight  228.30
_symmetry_cell_setting  Orthorhombic
_symmetry_space_group_name_H-M  'C m c a'
_symmetry_space_group_name_Hall  '-C 2bc 2'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y+1/2, z+1/2'
  '-x, y+1/2, -z+1/2'
  'x, -y, -z'
  'x+1/2, y+1/2, z'
  '-x+1/2, -y+1, z+1/2'
  '-x+1/2, y+1, -z+1/2'
  'x+1/2, -y+1/2, -z'
  '-x, -y, -z'
  'x, y-1/2, -z-1/2'
  'x, -y-1/2, z-1/2'
  '-x, y, z'
  '-x+1/2, -y+1/2, -z'
  'x+1/2, y, -z-1/2'
  'x+1/2, -y, z-1/2'
  '-x+1/2, y+1/2, z'
_cell_length_a  15.1714(9)
_cell_length_b  9.0190(5)
_cell_length_c  17.2111(10)
_cell_angle_alpha  90
_cell_angle_beta  90
_cell_angle_gamma  90
_cell_volume  2355.0(2)
_cell_formula_units_Z  8
_cell_measurement_temperature  100(2)
_exptl_crystal_density_diffrn  1.28
_exptl_crystal_density_meas  1.23
_diffrn_ambient_temperature  100(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
  O1 0.10535(5) 0.21627(7) 0.30402(4) 0.0237(2) Uani d . 1 . . O
  N1 0.09778(5) 0.63132(8) 0.43791(5) 0.0203(2) Uani d . 1 . . N
  H1NA 0.0942(13) 0.564(2) 0.4674(12) 0.013(5) Uiso d P 0.50 . . H
  H1NB 0.0534(14) 0.605(2) 0.4122(12) 0.013(5) Uiso d P 0.50 . . H
  N2 0.11837(5) 0.46558(8) 0.29273(4) 0.0188(2) Uani d . 1 . . N
  H2NA 0.1043(8) 0.5433(14) 0.2655(7) 0.029(3) Uiso d . 1 . . H
  C1 0.17912(5) 0.62745(10) 0.39300(5) 0.0204(2) Uani d . 1 . . C
  H1A 0.2300 0.6406 0.4284 0.029(3) Uiso calc R 1 . . H
  H1B 0.1793 0.7106 0.3554 0.024(3) Uiso calc R 1 . . H
  C2 0.18899(5) 0.48208(10) 0.34940(5) 0.0209(2) Uani d . 1 . . C
  H2A 0.2467 0.4799 0.3225 0.028(3) Uiso calc R 1 . . H
  H2B 0.1872 0.3985 0.3866 0.026(3) Uiso calc R 1 . . H
  C3 0.08071(6) 0.33573(9) 0.27639(5) 0.0181(2) Uani d . 1 . . C
  C4 0.0000 0.34517(13) 0.22393(7) 0.0198(3) Uani d S 1 . . C
  H4A 0.0000 0.2625 0.1861 0.029(4) Uiso calc SR 1 . . H
  H4B 0.0000 0.4399 0.1949 0.023(4) Uiso calc SR 1 . . H
  C5 0.08458(6) 0.77339(9) 0.47752(5) 0.0207(2) Uani d . 1 . . C
  H5A 0.0825 0.8539 0.4384 0.022(3) Uiso calc R 1 . . H
  H5B 0.1352 0.7926 0.5124 0.027(3) Uiso calc R 1 . . H
  C6 0.0000 0.77510(14) 0.52476(7) 0.0230(3) Uani d S 1 . . C
  H6A 0.0000 0.6878 0.5596 0.027(4) Uiso calc SR 1 . . H
  H6B 0.0000 0.8648 0.5579 0.035(5) Uiso calc SR 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
  O1 0.0351(4) 0.0139(3) 0.0221(3) 0.0037(2) 0.0003(3) 0.0006(2)
  N1 0.0178(4) 0.0166(4) 0.0265(4) -0.0029(3) 0.0017(3) -0.0031(3)
  N2 0.0207(4) 0.0141(4) 0.0217(4) 0.0018(3) 0.0012(3) 0.0024(3)
  C1 0.0150(4) 0.0203(4) 0.0259(4) -0.0032(3) -0.0019(3) 0.0022(3)
  C2 0.0153(4) 0.0208(4) 0.0265(4) 0.0023(3) 0.0020(3) 0.0025(3)
  C3 0.0248(4) 0.0155(4) 0.0142(4) 0.0024(3) 0.0061(3) -0.0012(3)
  C4 0.0318(7) 0.0142(5) 0.0134(5) 0.000 0.000 -0.0019(4)
  C5 0.0242(4) 0.0171(4) 0.0209(4) -0.0027(3) -0.0059(3) -0.0025(3)
  C6 0.0340(7) 0.0193(6) 0.0156(5) 0.000 0.000 -0.0044(4)
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
  O1 C3 . 1.2360(10)
  yes
  N1 C1 . 1.4570(10)
  yes
  N1 C5 . 1.4650(10)
  yes
  N1 H1NA . 0.80(2) yes
  N1 H1NB . 0.84(2) yes
  N2 C3 . 1.3330(10)
  yes
  N2 C2 . 1.4560(10)
  yes
  N2 H2NA . 0.870(10)
  yes
  C1 C2 . 1.518(2) no
  C1 H1A . 0.99 no
  C1 H1B . 0.99 no
  C2 H2A . 0.99 no
  C2 H2B . 0.99 no
  C3 C4 . 1.5240(10)
  no
  C4 H4A . 0.99 no
  C4 H4B . 0.99 no
  C5 C6 . 1.5190(10)
  no
  C5 H5A . 0.99 no
  C5 H5B . 0.99 no
  C6 H6A . 0.99 no
  C6 H6B . 0.99 no