#------------------------------------------------------------------------------ #$Date: 2015-04-02 12:22:18 +0100 (Thu, 02 Apr 2015) $ #$Revision: 134621 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/70/2007079.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, Thomas G.' 'Dyck, Brian P.' 'Nan, Siqiao' 'Parvez, Masood' _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' _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 425 _journal_page_last 427 _journal_paper_doi 10.1107/S0108270197015916 _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 .033 _refine_ls_shift/esd_max 0.003 _refine_ls_shift/esd_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.05P)^2^+0.5P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.088 _refine_ls_wR_factor_obs .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_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.05P)^2^+0.5P] where P = (Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.05P)^2^+0.5P] where P = (Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _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 .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_ _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_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_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 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