data_2006546
_journal_name_full  'Acta Crystallographica'
_journal_year  1997
_journal_volume  C53
_journal_page_first  1459
_journal_page_last  1462
_publ_section_title
;
2,4,6,8-Tetraazabicyclo[3.3.1]nonane-3,7-dione and
2,4,6,8-Tetraacetyl-2,4,6,8-tetraazabicyclo[3.3.1]nonane-3,7-dione
;
loop_
_publ_author_name
  'Piacenza, Guy'
  'Beguet, Christelle'
  'Wimmer, Eric'
  'Gallo, Roger'
  'Giorgi, Michel'
_chemical_formula_sum  'C13 H16 N4 O6'
_chemical_formula_weight  324.30
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_h-m  'P 21/c'
_cell_length_a  8.979(2)
_cell_length_b  16.265(6)
_cell_length_c  10.3420(10)
_cell_angle_alpha  90.00(2)
_cell_angle_beta  99.63(2)
_cell_angle_gamma  90.00(2)
_cell_volume  1489.0(10)
_cell_formula_units_z  4
_cell_measurement_temperature  294
_exptl_crystal_density_diffrn  1.45
_diffrn_ambient_temperature  294
_refine_ls_R_factor_obs  .047
_refine_ls_wR_factor_obs  .062
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
  N1  .4298(2)  .13760(10)
  .94520(10)
  .0351(4) Uani ?
  O1  .5021(2)  .02210(10)
  .84610(10)
  .0496(4) Uani ?
  N2  .2565(2)  .03230(10)
  .8739(2)  .0363(4) Uani ?
  O2  -.0372(2)  .05060(10)
  .7141(2)  .0711(5) Uani ?
  N3  .0881(2)  .14790(10)
  .84070(10)
  .0342(4) Uani ?
  C1  .1441(2)  .07970(10)
  .9298(2)  .0365(5) Uani ?
  C2  .4027(2)  .06090(10)
  .8835(2)  .0353(5) Uani ?
  O3  .3272(2)  .32570(10)
  1.1400(2)  .0599(5) Uani ?
  C3  .2185(2)  -.05150(10)
  .8410(2)  .0462(6) Uani ?
  N4  .2483(2)  .24320(10)
  .96660(10)
  .0366(4) Uani ?
  O4  .1306(2)  -.08590(10)
  .8980(2)  .0638(5) Uani ?
  C4  .5527(2)  .18810(10)
  .9288(2)  .0442(6) Uani ?
  C5  .3305(2)  .17290(10)
  1.0321(2)  .0363(5) Uani ?
  O5  .0538(2)  .28630(10)
  .8128(2)  .0648(5) Uani ?
  O6  .5688(2)  .25130(10)
  .9907(2)  .0688(5) Uani ?
  C6  -.0088(2)  .12310(10)
  .7257(2)  .0456(6) Uani ?
  C7  .2176(2)  .11110(10)
  1.0611(2)  .0385(5) Uani ?
  C8  .1257(2)  .23030(10)
  .8680(2)  .0389(5) Uani ?
  C9  .2832(3)  -.0911(2)  .7340(3)  .0706(8) Uani ?
  C10  -.0702(3)  .1832(2)  .6203(2)  .0593(7) Uani ?
  C11  .2817(3)  .32230(10)
  1.0244(2)  .0477(6) Uani ?
  C12  .6553(3)  .1658(2)  .8350(2)  .0569(7) Uani ?
  C13  .2667(4)  .3964(2)  .9386(3)  .0910(10)
  Uani ?
  H71  .2687  .0643 1.1185  .0489 Uiso calc
  H72  .1390  .1382 1.1095  .0489 Uiso calc
  H51  .3974  .1896 1.1176  .0449 Uiso calc
  H11  .0539  .0438  .9404  .0459 Uiso calc
  H91  .2459  -.1501  .7218  .0915 Uiso calc
  H92  .2499  -.0592  .6482  .0915 Uiso calc
  H93  .3982  -.0905  .7557  .0915 Uiso calc
  H101  -.1372  .1523  .5459  .0754 Uiso calc
  H102  -.1324  .2262  .6580  .0754 Uiso calc
  H103  .0168  .2102  .5849  .0754 Uiso calc
  H131  .2936  .4475  .9946  .1084 Uiso calc
  H132  .3368  .3909  .8719  .1084 Uiso calc
  H133  .1573  .4010  .8914  .1084 Uiso calc
  H121  .7375  .2089  .8361  .0707 Uiso calc
  H122  .7048  .1098  .8608  .0707 Uiso calc
  H123  .5947  .1611  .7421  .0707 Uiso calc
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  .0297(7)  .0403(9)  .0359(8)  .0013(7)  .0069(6)  .0021(8)
  O1  .0405(7)  .0495(8)  .0620(8)  .0082(7)  .0181(6)  -.0002(7)
  N2  .0346(8)  .0353(8)  .0395(8)  .0014(7)  .0077(7)  -.0002(7)
  O2  .0680(10)
  .0600(10)
  .0740(10)
  -.0083(9)  -.0201(9)  -.0136(9)
  N3  .0279(7)  .0418(9)  .0324(8)  .0017(7)  .0034(6)  -.0017(7)
  C1  .0319(9)  .0410(10)
  .0383(9)  -.0002(9)  .0100(8)  .0012(9)
  C2  .0339(9)  .0380(10)
  .0342(9)  .0054(8)  .0066(8)  .0044(8)
  O3  .0637(9)  .0650(10)
  .0492(8)  -.0030(8)  .0032(7)  -.0211(8)
  C3  .0450(10)
  .0430(10)
  .0490(10)
  .0010(10)
  .0020(10)
  .0000(10)
  N4  .0376(8)  .0378(9)  .0332(8)  .0013(7)  .0027(7)  -.0036(7)
  O4  .0660(10)
  .0478(9)  .0790(10)
  -.0148(8)  .0178(8)  .0003(8)
  C4  .0330(10)
  .0490(10)
  .0500(10)
  -.0025(9)  .0031(9)  .0010(10)
  C5  .0331(9)  .0440(10)
  .0309(9)  .0046(9)  .0035(8)  .0000(9)
  O5  .0750(10)
  .0469(9)  .0620(10)
  .0170(8)  -.0187(9)  .0038(8)
  O6  .0481(8)  .0680(10)
  .0920(10)
  -.0200(8)  .0177(8)  -.0219(9)
  C6  .0320(10)
  .0580(10)
  .0440(10)
  .0010(10)
  .0004(9)  -.0080(10)
  C7  .0380(10)
  .0480(10)
  .0314(9)  .0030(9)  .0096(8)  .0055(9)
  C8  .0370(10)
  .0440(10)
  .0350(10)
  .0064(9)  .0055(8)  .0001(9)
  C9  .078(2)  .062(2)  .074(2)  -.0020(10)
  .0170(10)
  -.0270(10)
  C10  .0520(10)
  .084(2)  .0370(10)
  .0020(10)
  -.0060(10)
  .0010(10)
  C11  .0480(10)
  .0470(10)
  .0480(10)
  .0020(10)
  .0074(9)  -.0100(10)
  C12  .0430(10)
  .068(2)  .0650(10)
  -.0050(10)
  .0240(10)
  .0070(10)
  C13  .132(3)  .0420(10)
  .089(2)  -.013(2)  -.010(2)  .0010(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
  N1 C2 1.404(3) no
  N1 C4 1.408(3) no
  N1 C5 1.483(3) no
  O1 C2 1.208(3) yes
  N2 C1 1.464(3) yes
  N2 C2 1.381(2) yes
  N2 C3 1.432(3) yes
  O2 C6 1.208(3) no
  N3 C1 1.475(2) no
  N3 C6 1.410(2) no
  N3 C8 1.400(3) no
  C1 C7 1.497(3) yes
  O3 C11 1.199(3) no
  C3 O4 1.200(3) yes
  C3 C9 1.480(4) yes
  N4 C5 1.465(2) no
  N4 C8 1.385(2) no
  N4 C11 1.429(3) no
  C4 O6 1.206(3) no
  C4 C12 1.491(3) no
  C5 C7 1.492(3) no
  O5 C8 1.204(3) no
  C6 C10 1.499(3) no
  C11 C13 1.490(4) no