#------------------------------------------------------------------------------ #$Date: 2013-08-29 16:37:19 +0100 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/89/2008961.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_2008961 loop_ _publ_author_name 'Homrighausen, Craig L.' 'Krause Bauer, Jeanette A.' _publ_section_title ; 2,2,6,6-Tetramethyl-4-(methylsulfonyloxy)piperidinyl 1-oxide ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first IUC9900102 _journal_volume 55 _journal_year 1999 _chemical_formula_sum 'C10 H20 N O4 S' _chemical_formula_weight 250.33 _chemical_melting_point 364.6(5) _chemical_name_systematic ; 2,2,6,6-tetramethyl-4-(methylsulfonyl-oxyl)-1-piperidinooxy ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _audit_creation_method SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 113.52(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 12.951(3) _cell_length_b 9.977(2) _cell_length_c 11.131(2) _cell_measurement_reflns_used 30 _cell_measurement_temperature 297(2) _cell_measurement_theta_max 15.0 _cell_measurement_theta_min 5.0 _cell_volume 1318.8(6) _computing_cell_refinement P3/P4-PC _computing_data_collection 'P3/P4-PC (Siemens, 1989)' _computing_data_reduction 'XDISK (Siemens, 1989)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1994)' _diffrn_ambient_temperature 297(2) _diffrn_measurement_device_type 'Siemens P3' _diffrn_measurement_method \q-2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.012 _diffrn_reflns_av_sigmaI/netI 0.043 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 3200 _diffrn_reflns_theta_max 27.55 _diffrn_reflns_theta_min 2.67 _diffrn_standards_decay_% minimal _diffrn_standards_interval_count 300 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.245 _exptl_absorpt_correction_type none _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.261 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'irregular block' _exptl_crystal_F_000 540 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.30 _refine_diff_density_max 0.19 _refine_diff_density_min -0.37 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 145 _refine_ls_number_reflns 3042 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.073 _refine_ls_R_factor_all 0.091 _refine_ls_R_factor_gt 0.053 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0504P)^2^+0.4212P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.129 _reflns_number_gt 2024 _reflns_number_total 3042 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file qa0158.cif _[local]_cod_data_source_block 1 _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_chemical_melting_point' value '91-92\% C' was changed to '364.6(5)' - it was converted from degrees Celsius(C) to Kelvins(K), the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '91-92\% C' was changed to '364.6(5)' - it was converted from degrees Celsius(C) to Kelvins(K), the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 1318.8(5) _cod_database_code 2008961 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -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 S1 0.0479(3) 0.0520(4) 0.0413(3) 0.0002(3) 0.0245(3) -0.0062(3) O1 0.0539(11) 0.0527(11) 0.094(2) -0.0018(9) 0.0424(11) -0.0185(11) O2 0.0436(10) 0.0761(14) 0.0796(14) -0.0062(10) 0.0242(10) -0.0210(11) O3 0.0458(10) 0.0549(11) 0.0362(9) 0.0032(8) 0.0136(7) -0.0078(8) O4 0.0879(14) 0.0726(13) 0.0498(11) 0.0026(11) 0.0447(10) -0.0086(10) N1 0.0370(10) 0.0386(12) 0.0559(12) 0.0006(9) 0.0222(9) -0.0004(9) C1 0.096(2) 0.055(2) 0.055(2) 0.013(2) 0.040(2) 0.0066(14) C2 0.0363(12) 0.0370(13) 0.064(2) -0.0005(10) 0.0241(11) 0.0003(12) C3 0.0384(13) 0.0429(14) 0.057(2) -0.0044(11) 0.0160(11) -0.0034(12) C4 0.0378(12) 0.0429(14) 0.0331(11) 0.0021(10) 0.0148(10) -0.0018(10) C5 0.0388(12) 0.0467(15) 0.0457(14) -0.0026(11) 0.0202(11) 0.0023(11) C6 0.0334(12) 0.0421(14) 0.0522(14) -0.0048(10) 0.0171(10) -0.0029(11) C7 0.081(2) 0.055(2) 0.088(2) 0.006(2) 0.060(2) 0.014(2) C8 0.0345(13) 0.057(2) 0.117(3) -0.0053(13) 0.028(2) -0.014(2) C9 0.0460(15) 0.076(2) 0.052(2) 0.0043(14) 0.0096(12) -0.0160(15) C10 0.060(2) 0.043(2) 0.110(3) -0.0099(13) 0.049(2) -0.005(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 S1 0.86464(5) 0.29787(7) 0.14934(6) 0.0450(2) Uani d . 1 . S O1 0.62040(15) 0.7505(2) 0.3926(2) 0.0627(6) Uani d . 1 . O O2 0.95838(15) 0.3769(2) 0.2272(2) 0.0665(6) Uani d . 1 . O O3 0.75320(13) 0.3775(2) 0.11908(15) 0.0466(4) Uani d . 1 . O O4 0.8566(2) 0.2515(2) 0.0248(2) 0.0647(6) Uani d . 1 . O N1 0.6504(2) 0.6670(2) 0.3249(2) 0.0427(5) Uani d . 1 . N C1 0.8547(3) 0.1598(3) 0.2404(3) 0.0657(8) Uani d . 1 . C H1A 0.7914 0.1059 0.1881 0.098 Uiso calc R 1 . H H1B 0.8451 0.1902 0.3171 0.098 Uiso calc R 1 . H H1C 0.9224 0.1075 0.2662 0.098 Uiso calc R 1 . H C2 0.5827(2) 0.5410(2) 0.2863(3) 0.0443(6) Uani d . 1 . C C3 0.6138(2) 0.4635(3) 0.1869(2) 0.0470(6) Uani d . 1 . C H3A 0.5843 0.3731 0.1793 0.056 Uiso calc R 1 . H H3B 0.5782 0.5061 0.1018 0.056 Uiso calc R 1 . H C4 0.7388(2) 0.4569(2) 0.2237(2) 0.0377(5) Uani d . 1 . C H4 0.7767(2) 0.4131(2) 0.3090(2) 0.045 Uiso calc R 1 . H C5 0.7828(2) 0.5969(2) 0.2269(2) 0.0427(6) Uani d . 1 . C H5A 0.7433 0.6388 0.1421 0.051 Uiso calc R 1 . H H5B 0.8621 0.5929 0.2431 0.051 Uiso calc R 1 . H C6 0.7678(2) 0.6820(2) 0.3326(2) 0.0426(6) Uani d . 1 . C C7 0.6034(3) 0.4576(3) 0.4087(3) 0.0665(8) Uani d . 1 . C H7A 0.6813 0.4322 0.4485 0.100 Uiso calc R 1 . H H7B 0.5574 0.3785 0.3849 0.100 Uiso calc R 1 . H H7C 0.5845 0.5096 0.4697 0.100 Uiso calc R 1 . H C8 0.4590(2) 0.5814(3) 0.2230(3) 0.0704(9) Uani d . 1 . C H8A 0.4461 0.6340 0.1461 0.106 Uiso calc R 1 . H H8B 0.4402 0.6333 0.2840 0.106 Uiso calc R 1 . H H8C 0.4130 0.5024 0.1991 0.106 Uiso calc R 1 . H C9 0.8518(2) 0.6423(3) 0.4696(3) 0.0612(8) Uani d . 1 . C H9A 0.8404 0.6975 0.5338 0.092 Uiso calc R 1 . H H9B 0.9272 0.6544 0.4754 0.092 Uiso calc R 1 . H H9C 0.8407 0.5499 0.4856 0.092 Uiso calc R 1 . H C10 0.7833(2) 0.8300(3) 0.3081(3) 0.0662(9) Uani d . 1 . C H10A 0.7738 0.8835 0.3746 0.099 Uiso calc R 1 . H H10B 0.7283 0.8556 0.2237 0.099 Uiso calc R 1 . H H10C 0.8575 0.8437 0.3106 0.099 Uiso calc R 1 . H 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 S1 O2 . 1.417(2) y S1 O4 . 1.425(2) y S1 O3 . 1.562(2) y S1 C1 . 1.745(3) y O1 N1 . 1.283(3) y O3 C4 . 1.480(3) y N1 C2 . 1.495(3) y N1 C6 . 1.496(3) y C2 C7 . 1.526(4) y C2 C8 . 1.524(4) y C2 C3 . 1.529(3) y C3 C4 . 1.505(3) y C4 C5 . 1.504(3) y C5 C6 . 1.526(3) y C6 C10 . 1.529(3) y C6 C9 . 1.530(3) y loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 O2 S1 O4 119.20(10) y O2 S1 O3 109.90(10) y O4 S1 O3 104.60(10) y O2 S1 C1 109.1(2) y O4 S1 C1 108.40(10) y O3 S1 C1 104.50(10) y C4 O3 S1 119.90(10) y O1 N1 C2 115.7(2) y O1 N1 C6 116.1(2) y C2 N1 C6 124.5(2) y N1 C2 C7 109.2(2) y N1 C2 C8 107.3(2) y C7 C2 C8 109.5(2) y N1 C2 C3 109.9(2) y C7 C2 C3 111.5(2) y C8 C2 C3 109.3(2) y C4 C3 C2 113.0(2) y O3 C4 C5 110.4(2) y O3 C4 C3 105.6(2) y C5 C4 C3 108.8(2) y C4 C5 C6 111.8(2) y N1 C6 C5 109.8(2) y N1 C6 C10 106.8(2) y C5 C6 C10 109.5(2) y N1 C6 C9 109.5(2) y C5 C6 C9 111.5(2) y C10 C6 C9 109.7(2) y loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag C1 H1B O4 4_566 0.96 2.33 3.278(3) 170 y C7 H7A O4 4_566 0.96 2.77 3.659(4) 154 y C8 H8C O1 3_645 0.96 2.68 3.544(4) 150 y C10 H10C O2 3_755 0.96 2.60 3.552(3) 170 y 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 O2 S1 O3 C4 -42.3(2) n O4 S1 O3 C4 -171.5(2) n C1 S1 O3 C4 74.7(2) n O1 N1 C2 C7 -67.4(3) n C6 N1 C2 C7 90.4(3) n O1 N1 C2 C8 51.2(3) n C6 N1 C2 C8 -151.0(2) n O1 N1 C2 C3 170.0(2) n C6 N1 C2 C3 -32.3(3) n N1 C2 C3 C4 44.5(3) n C7 C2 C3 C4 -76.7(3) n C8 C2 C3 C4 162.0(2) n S1 O3 C4 C5 88.9(2) n S1 O3 C4 C3 -153.6(2) n C2 C3 C4 O3 179.2(2) n C2 C3 C4 C5 -62.3(3) n O3 C4 C5 C6 179.2(2) n C3 C4 C5 C6 63.8(2) n O1 N1 C6 C5 -168.3(2) n C2 N1 C6 C5 34.1(3) n O1 N1 C6 C10 -49.6(3) n C2 N1 C6 C10 152.7(2) n O1 N1 C6 C9 69.0(3) n C2 N1 C6 C9 -88.6(3) n C4 C5 C6 N1 -47.7(3) n C4 C5 C6 C10 -164.7(2) n C4 C5 C6 C9 73.8(2) n _cod_database_fobs_code 2008961