data_2007079
_journal_name_full  'Acta Crystallographica'
_journal_year  1998
_journal_volume  C54
_journal_page_first  425
_journal_page_last  427
_publ_section_title
;
[3aR-(3a\a,4\a,7\a,7a\a)]-2-Acetyl-4,8,8-trimethylperhydro-4,7-methano-
1,2-benzisoselenazol-3a-ol
;
loop_
_publ_author_name
  'Back*, Thomas G.'
  'Dyck, Brian P.'
  'Nan, Siqiao'
  'Parvez*, Masood'
_chemical_name_common  'Cyclic Selenenamide'
_chemical_formula_moiety  'C13 H21 N O2 Se'
_chemical_formula_sum  'C13 H21 N O2 Se'
_chemical_formula_structural  'C13 H21 N O2 Se'
_chemical_formula_analytical  'C13 H21 N O2 Se'
_chemical_formula_weight  302.27
_symmetry_cell_setting  orthorhombic
_symmetry_space_group_name_H-M  'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, -y, z+1/2'
  'x+1/2, -y+1/2, -z'
  '-x, y+1/2, -z+1/2'
_cell_length_a  6.8684(10)
_cell_length_b  11.537(2)
_cell_length_c  17.079(3)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  1353.4(4)
_cell_formula_units_Z  4
_cell_measurement_temperature  293.0(10)
_exptl_crystal_density_diffrn  1.483
_diffrn_ambient_temperature  293.0(10)
_refine_ls_R_factor_obs  .033
_refine_ls_wR_factor_obs  .085
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
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
  Se1  .52873(6)  .22740(4)  .81771(2)  .04185(13) Uani d . 1 . Se
  O1  .3243(4)  -.0642(3)  .7847(2)  .0499(8) Uani d . 1 . O
  O2  -.0274(5)  .3323(3)  .7998(2)  .0630(9) Uani d . 1 . O
  N1  .2616(5)  .2398(3)  .7999(2)  .0433(8) Uani d . 1 . N
  C1  .1818(7)  .1254(4)  .7815(2)  .0444(10) Uani d . 1 . C
  C2  .2777(5)  .0325(3)  .8331(2)  .0336(8) Uani d . 1 . C
  C3  .4741(6)  .0794(3)  .8675(2)  .0357(7) Uani d . 1 . C
  C4  .4428(6)  .0750(3)  .9565(2)  .0414(9) Uani d . 1 . C
  C5  .2895(7)  .1644(4)  .9798(2)  .0492(10) Uani d . 1 . C
  C6  .0994(6)  .1096(3)  .9490(3)  .0459(10) Uani d . 1 . C
  C7  .1660(5)  -.0036(3)  .9089(2)  .0338(8) Uani d . 1 . C
  C8  .3324(6)  -.0413(4)  .9657(3)  .0433(10) Uani d . 1 . C
  C9  .0032(6)  -.0891(4)  .8952(3)  .0510(10) Uani d . 1 . C
  C10  .2664(9)  -.0637(5) 1.0502(3)  .069(2) Uani d . 1 . C
  C11  .4487(7)  -.1487(4)  .9406(3)  .0672(14) Uani d . 1 . C
  C12  .1519(6)  .3358(4)  .8091(3)  .0459(10) Uani d . 1 . C
  C13  .2536(7)  .4458(4)  .8311(3)  .0577(12) Uani d . 1 . C
  H1  .2115  -.0878  .7567  .082(4) Uiso calc R 1 . H
  H1A  .2045  .1081  .7279  .082(4) Uiso calc R 1 . H
  H1B  .0451  .1255  .7901  .082(4) Uiso calc R 1 . H
  H3  .5750  .0267  .8542  .082(4) Uiso calc R 1 . H
  H4  .5596  .0796  .9862  .082(4) Uiso calc R 1 . H
  H5A  .3138  .2371  .9556  .082(4) Uiso calc R 1 . H
  H5B  .2853  .1746 1.0349  .082(4) Uiso calc R 1 . H
  H6A  .0123  .0937  .9908  .082(4) Uiso calc R 1 . H
  H6B  .0369  .1595  .9126  .082(4) Uiso calc R 1 . H
  H9A  .0537  -.1565  .8705  .082(4) Uiso calc R 1 . H
  H9B  -.0928  -.0548  .8625  .082(4) Uiso calc R 1 . H
  H9C  -.0538  -.1099  .9439  .082(4) Uiso calc R 1 . H
  H10A  .1934  .0008 1.0685  .082(4) Uiso calc R 1 . H
  H10B  .3773  -.0744 1.0827  .082(4) Uiso calc R 1 . H
  H10C  .1876  -.1313 1.0518  .082(4) Uiso calc R 1 . H
  H11A  .4927  -.1390  .8883  .082(4) Uiso calc R 1 . H
  H11B  .3677  -.2153  .9437  .082(4) Uiso calc R 1 . H
  H11C  .5575  -.1582  .9743  .082(4) Uiso calc R 1 . H
  H13A  .3895  .4317  .8354  .082(4) Uiso calc R 1 . H
  H13B  .2049  .4728  .8798  .082(4) Uiso calc R 1 . H
  H13C  .2311  .5026  .7919  .082(4) Uiso calc R 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
  Se1  .0338(2)  .0424(2)  .0494(2)  -.0053(2)  .0021(2)  .0074(2)
  O1  .041(2)  .053(2)  .056(2)  -.0049(13)  .0096(13)  -.0275(15)
  O2  .042(2)  .071(2)  .076(2)  .012(2)  -.006(2)  .024(2)
  N1  .040(2)  .046(2)  .044(2)  -.0003(14)  -.0044(12)  .0087(14)
  C1  .043(2)  .054(3)  .036(2)  -.004(2)  -.003(2)  -.002(2)
  C2  .027(2)  .035(2)  .039(2)  -.0023(14)  .000(2)  -.008(2)
  C3  .028(2)  .034(2)  .045(2)  -.002(2)  -.004(2)  -.0016(14)
  C4  .045(2)  .041(2)  .039(2)  -.010(2)  -.010(2)  .006(2)
  C5  .072(3)  .041(2)  .035(2)  -.008(2)  .007(2)  -.008(2)
  C6  .049(2)  .042(2)  .046(2)  .002(2)  .016(2)  -.006(2)
  C7  .032(2)  .032(2)  .038(2)  -.0033(15)  .003(2)  -.004(2)
  C8  .043(2)  .036(2)  .050(2)  -.008(2)  -.008(2)  .008(2)
  C9  .040(3)  .052(2)  .062(2)  -.014(2)  .003(2)  -.004(2)
  C10  .087(4)  .066(3)  .054(3)  -.023(3)  -.006(3)  .021(3)
  C11  .052(3)  .039(2)  .111(4)  .001(2)  -.011(3)  .022(2)
  C12  .046(2)  .055(3)  .036(2)  .007(2)  .001(2)  .020(2)
  C13  .063(3)  .040(2)  .069(3)  .009(2)  .013(3)  .010(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
  Se1 N1 . 1.865(3) y
  Se1 C3 . 1.943(3) y
  O1 C2 . 1.425(4) y
  O2 C12 . 1.243(5) y
  N1 C12 . 1.348(5) y
  N1 C1 . 1.463(5) y
  C1 C2 . 1.537(6) n
  C2 C7 . 1.561(5) n
  C2 C3 . 1.567(5) n
  C3 C4 . 1.537(5) n
  C4 C5 . 1.526(6) n
  C4 C8 . 1.549(5) n
  C5 C6 . 1.543(6) n
  C6 C7 . 1.543(5) n
  C7 C9 . 1.510(5) n
  C7 C8 . 1.561(6) n
  C8 C10 . 1.535(6) n
  C8 C11 . 1.535(6) n
  C12 C13 . 1.496(7) n