#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2007079.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2007079
loop_
_publ_author_name
'Back, T. G.'
'Dyck, B. P.'
'Nan, S.'
'Parvez, M.'
_publ_section_title
;
 [3a<i>R</i>-(3a\a,4\a,7\a,7a\a)]-2-Acetyl-4,8,8-trimethylperhydro-4,7-methano-1,2-benzisoselenazol-3a-ol
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              425
_journal_page_last               427
_journal_volume                  54
_journal_year                    1998
_chemical_formula_analytical     'C13 H21 N O2 Se'
_chemical_formula_moiety         'C13 H21 N O2 Se'
_chemical_formula_structural     'C13 H21 N O2 Se'
_chemical_formula_sum            'C13 H21 N O2 Se'
_chemical_formula_weight         302.27
_chemical_name_common            'Cyclic Selenenamide'
_chemical_name_systematic
;
[3aR-(3a\a,4\a,7\a,7a\a)]-2-Acetylhexahydro-4,8,8-trimethyl-4,7-methano-
1,2-benzisoselenazol-3a(4H)-ol
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.8684(10)
_cell_length_b                   11.537(2)
_cell_length_c                   17.079(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293.0(10)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      20
_cell_volume                     1353.4(4)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Schagen et al., 1989)'
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1994)'
_computing_molecular_graphics    TEXSAN
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SAPI91 (Fan, 1991)'
_diffrn_ambient_temperature      293.0(10)
_diffrn_measurement_device       'Enraf-Nonius CAD4'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.049
_diffrn_reflns_av_sigmaI/netI    0.0328
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            2802
_diffrn_reflns_theta_max         68.0
_diffrn_reflns_theta_min         5.0
_diffrn_standards_decay_%        4.62
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    3.684
_exptl_absorpt_correction_T_max  0.692
_exptl_absorpt_correction_T_min  0.605
_exptl_absorpt_correction_type   'empirical via \y scan of three reflections'
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.529
_refine_ls_abs_structure_details 'Flack (1983)'
_refine_ls_abs_structure_Flack   0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.113
_refine_ls_goodness_of_fit_obs   1.107
_refine_ls_hydrogen_treatment    'H atoms riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2466
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.113
_refine_ls_restrained_S_obs      1.107
_refine_ls_R_factor_all          0.037
_refine_ls_R_factor_obs          0.033
_refine_ls_shift/esd_max         0.003
_refine_ls_shift/esd_mean        0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.05P)^2^+0.5P] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.088
_refine_ls_wR_factor_obs         0.085
_reflns_number_observed          2303
_reflns_number_total             2466
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    fg1405.cif
_[local]_cod_data_source_block   I
_cod_database_code               2007079
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'
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 0.0338(2) 0.0424(2) 0.0494(2) -0.0053(2) 0.0021(2) 0.0074(2)
O1 0.041(2) 0.053(2) 0.056(2) -0.0049(13) 0.0096(13) -0.0275(15)
O2 0.042(2) 0.071(2) 0.076(2) 0.012(2) -0.006(2) 0.024(2)
N1 0.040(2) 0.046(2) 0.044(2) -0.0003(14) -0.0044(12) 0.0087(14)
C1 0.043(2) 0.054(3) 0.036(2) -0.004(2) -0.003(2) -0.002(2)
C2 0.027(2) 0.035(2) 0.039(2) -0.0023(14) 0.000(2) -0.008(2)
C3 0.028(2) 0.034(2) 0.045(2) -0.002(2) -0.004(2) -0.0016(14)
C4 0.045(2) 0.041(2) 0.039(2) -0.010(2) -0.010(2) 0.006(2)
C5 0.072(3) 0.041(2) 0.035(2) -0.008(2) 0.007(2) -0.008(2)
C6 0.049(2) 0.042(2) 0.046(2) 0.002(2) 0.016(2) -0.006(2)
C7 0.032(2) 0.032(2) 0.038(2) -0.0033(15) 0.003(2) -0.004(2)
C8 0.043(2) 0.036(2) 0.050(2) -0.008(2) -0.008(2) 0.008(2)
C9 0.040(3) 0.052(2) 0.062(2) -0.014(2) 0.003(2) -0.004(2)
C10 0.087(4) 0.066(3) 0.054(3) -0.023(3) -0.006(3) 0.021(3)
C11 0.052(3) 0.039(2) 0.111(4) 0.001(2) -0.011(3) 0.022(2)
C12 0.046(2) 0.055(3) 0.036(2) 0.007(2) 0.001(2) 0.020(2)
C13 0.063(3) 0.040(2) 0.069(3) 0.009(2) 0.013(3) 0.010(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_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
Se1 0.52873(6) 0.22740(4) 0.81771(2) 0.04185(13) Uani d . 1 Se
O1 0.3243(4) -0.0642(3) 0.7847(2) 0.0499(8) Uani d . 1 O
O2 -0.0274(5) 0.3323(3) 0.7998(2) 0.0630(9) Uani d . 1 O
N1 0.2616(5) 0.2398(3) 0.7999(2) 0.0433(8) Uani d . 1 N
C1 0.1818(7) 0.1254(4) 0.7815(2) 0.0444(10) Uani d . 1 C
C2 0.2777(5) 0.0325(3) 0.8331(2) 0.0336(8) Uani d . 1 C
C3 0.4741(6) 0.0794(3) 0.8675(2) 0.0357(7) Uani d . 1 C
C4 0.4428(6) 0.0750(3) 0.9565(2) 0.0414(9) Uani d . 1 C
C5 0.2895(7) 0.1644(4) 0.9798(2) 0.0492(10) Uani d . 1 C
C6 0.0994(6) 0.1096(3) 0.9490(3) 0.0459(10) Uani d . 1 C
C7 0.1660(5) -0.0036(3) 0.9089(2) 0.0338(8) Uani d . 1 C
C8 0.3324(6) -0.0413(4) 0.9657(3) 0.0433(10) Uani d . 1 C
C9 0.0032(6) -0.0891(4) 0.8952(3) 0.0510(10) Uani d . 1 C
C10 0.2664(9) -0.0637(5) 1.0502(3) 0.069(2) Uani d . 1 C
C11 0.4487(7) -0.1487(4) 0.9406(3) 0.0672(14) Uani d . 1 C
C12 0.1519(6) 0.3358(4) 0.8091(3) 0.0459(10) Uani d . 1 C
C13 0.2536(7) 0.4458(4) 0.8311(3) 0.0577(12) Uani d . 1 C
H1 0.2115 -0.0878 0.7567 0.082(4) Uiso calc R 1 H
H1A 0.2045 0.1081 0.7279 0.082(4) Uiso calc R 1 H
H1B 0.0451 0.1255 0.7901 0.082(4) Uiso calc R 1 H
H3 0.5750 0.0267 0.8542 0.082(4) Uiso calc R 1 H
H4 0.5596 0.0796 0.9862 0.082(4) Uiso calc R 1 H
H5A 0.3138 0.2371 0.9556 0.082(4) Uiso calc R 1 H
H5B 0.2853 0.1746 1.0349 0.082(4) Uiso calc R 1 H
H6A 0.0123 0.0937 0.9908 0.082(4) Uiso calc R 1 H
H6B 0.0369 0.1595 0.9126 0.082(4) Uiso calc R 1 H
H9A 0.0537 -0.1565 0.8705 0.082(4) Uiso calc R 1 H
H9B -0.0928 -0.0548 0.8625 0.082(4) Uiso calc R 1 H
H9C -0.0538 -0.1099 0.9439 0.082(4) Uiso calc R 1 H
H10A 0.1934 0.0008 1.0685 0.082(4) Uiso calc R 1 H
H10B 0.3773 -0.0744 1.0827 0.082(4) Uiso calc R 1 H
H10C 0.1876 -0.1313 1.0518 0.082(4) Uiso calc R 1 H
H11A 0.4927 -0.1390 0.8883 0.082(4) Uiso calc R 1 H
H11B 0.3677 -0.2153 0.9437 0.082(4) Uiso calc R 1 H
H11C 0.5575 -0.1582 0.9743 0.082(4) Uiso calc R 1 H
H13A 0.3895 0.4317 0.8354 0.082(4) Uiso calc R 1 H
H13B 0.2049 0.4728 0.8798 0.082(4) Uiso calc R 1 H
H13C 0.2311 0.5026 0.7919 0.082(4) Uiso calc R 1 H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0492 .0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
N1 Se1 C3 87.1(2) y
C12 N1 C1 123.8(3) y
C12 N1 Se1 126.4(3) y
C1 N1 Se1 109.5(3) y
N1 C1 C2 110.2(3) n
O1 C2 C1 108.0(3) n
O1 C2 C7 112.5(3) n
C1 C2 C7 116.8(3) n
O1 C2 C3 107.1(3) n
C1 C2 C3 110.0(3) n
C7 C2 C3 101.8(3) n
C4 C3 C2 103.8(3) n
C4 C3 Se1 119.3(2) n
C2 C3 Se1 107.8(2) n
C5 C4 C3 109.4(3) n
C5 C4 C8 102.8(3) n
C3 C4 C8 101.4(3) n
C4 C5 C6 102.6(3) n
C7 C6 C5 104.3(3) n
C9 C7 C6 113.7(3) n
C9 C7 C8 117.2(3) n
C6 C7 C8 100.2(3) n
C9 C7 C2 114.1(3) n
C6 C7 C2 106.7(3) n
C8 C7 C2 103.3(3) n
C10 C8 C11 106.3(4) n
C10 C8 C4 112.7(4) n
C11 C8 C4 114.6(4) n
C10 C8 C7 114.5(4) n
C11 C8 C7 115.6(4) n
C4 C8 C7 93.1(3) n
O2 C12 N1 120.8(4) n
O2 C12 C13 121.5(4) n
N1 C12 C13 117.7(4) n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_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
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
C3 Se1 N1 C12 137.5(3) n
C3 Se1 N1 C1 -36.8(3) n
C12 N1 C1 C2 -135.2(4) n
Se1 N1 C1 C2 39.3(4) n
N1 C1 C2 O1 -135.8(3) n
N1 C1 C2 C7 96.2(4) n
N1 C1 C2 C3 -19.2(5) n
O1 C2 C3 C4 -123.3(3) n
C1 C2 C3 C4 119.5(3) n
C7 C2 C3 C4 -5.0(4) n
O1 C2 C3 Se1 109.2(3) n
C1 C2 C3 Se1 -7.9(4) n
C7 C2 C3 Se1 -132.4(2) n
N1 Se1 C3 C4 -93.4(3) n
N1 Se1 C3 C2 24.5(2) n
C2 C3 C4 C5 -68.1(4) n
Se1 C3 C4 C5 51.8(4) n
C2 C3 C4 C8 40.0(4) n
Se1 C3 C4 C8 159.9(3) n
C3 C4 C5 C6 72.5(4) n
C8 C4 C5 C6 -34.6(4) n
C4 C5 C6 C7 -1.9(4) n
C5 C6 C7 C9 163.0(3) n
C5 C6 C7 C8 37.1(4) n
C5 C6 C7 C2 -70.2(4) n
O1 C2 C7 C9 -45.3(4) n
C1 C2 C7 C9 80.4(4) n
C3 C2 C7 C9 -159.7(3) n
O1 C2 C7 C6 -171.9(3) n
C1 C2 C7 C6 -46.1(4) n
C3 C2 C7 C6 73.8(4) n
O1 C2 C7 C8 83.0(4) n
C1 C2 C7 C8 -151.2(3) n
C3 C2 C7 C8 -31.4(4) n
C5 C4 C8 C10 -62.2(4) n
C3 C4 C8 C10 -175.3(4) n
C5 C4 C8 C11 176.1(4) n
C3 C4 C8 C11 63.0(5) n
C5 C4 C8 C7 56.0(3) n
C3 C4 C8 C7 -57.1(3) n
C9 C7 C8 C10 -62.7(5) n
C6 C7 C8 C10 60.9(4) n
C2 C7 C8 C10 170.9(3) n
C9 C7 C8 C11 61.4(5) n
C6 C7 C8 C11 -175.0(4) n
C2 C7 C8 C11 -65.0(4) n
C9 C7 C8 C4 -179.3(3) n
C6 C7 C8 C4 -55.8(3) n
C2 C7 C8 C4 54.3(3) n
C1 N1 C12 O2 -2.3(7) n
Se1 N1 C12 O2 -175.8(3) n
C1 N1 C12 C13 177.6(4) n
Se1 N1 C12 C13 4.0(5) n