#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/88/2008898.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_2008898 loop_ _publ_author_name 'Rochon, Fernande D.' 'Breau, Livain' _publ_section_title (+)-(2S,7R,9R,10S)-2-Ethenyl-4,4,7-trimethyl-3-(toluene-4-sulfonyl)-3,4,4a,5,6,7,8,8a-octahydro-2H-1,3-benzoxazine _journal_issue 9 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1587 _journal_page_last 1589 _journal_paper_doi 10.1107/S0108270199006873 _journal_volume 55 _journal_year 1999 _chemical_formula_sum 'C20 H29 N O3 S' _chemical_formula_weight 363.50 _chemical_name_systematic ; (+)-(2S,7R,9R,10S)-2-Ethenyl-4,4,7- trimethyl-3-(toluene-4-sulfonyl)perhydro-1,3-benzoxazine ; _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' _audit_creation_method SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.843(3) _cell_length_b 14.085(5) _cell_length_c 15.638(5) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 9.25 _cell_measurement_theta_min 3.86 _cell_volume 1947.8(11) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Siemens, 1996)' _computing_data_reduction XSCANS _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1995)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '2\q/\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.000 _diffrn_reflns_av_sigmaI/netI 0.076 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 3204 _diffrn_reflns_theta_max 30 _diffrn_reflns_theta_min 2.60 _diffrn_standards_decay_% 9.9 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.184 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.240 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 784 _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.17 _refine_diff_density_max 0.16 _refine_diff_density_min -0.16 _refine_ls_abs_structure_details 'Flack (1983)' _refine_ls_abs_structure_Flack 0.04(13) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.046 _refine_ls_goodness_of_fit_obs 1.286 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 274 _refine_ls_number_reflns 3204 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.046 _refine_ls_restrained_S_obs 1.286 _refine_ls_R_factor_all 0.138 _refine_ls_R_factor_obs 0.053 _refine_ls_shift/esd_max <0.001 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0120P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.099 _refine_ls_wR_factor_obs 0.081 _reflns_number_observed 1558 _reflns_number_total 3204 _reflns_observed_criterion I>2\s(I) _cod_data_source_file fr1189.cif _cod_data_source_block global _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' 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: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' 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_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.0120P)^2^] 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^)+(0.0120P)^2^] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 1947.9(12) _cod_original_sg_symbol_H-M 'P21 21 21' _cod_database_code 2008898 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' 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 S 0.0613(3) 0.0572(2) 0.0591(3) 0.0010(3) 0.0128(3) 0.0097(3) O1 0.0594(8) 0.0991(9) 0.0381(6) -0.0149(8) -0.0089(6) -0.0018(7) O2 0.0857(9) 0.0859(9) 0.0583(7) 0.0232(8) 0.0221(8) 0.0301(7) O3 0.0653(8) 0.0598(8) 0.0983(10) -0.0121(8) 0.0135(9) -0.0020(8) N3 0.0504(8) 0.0619(8) 0.0420(8) 0.0057(9) 0.0000(7) 0.0053(8) C2 0.0522(10) 0.0761(11) 0.0369(8) 0.0108(11) 0.0023(9) 0.0064(10) C4 0.0555(10) 0.0623(11) 0.0432(9) 0.0065(11) -0.0104(9) -0.0042(9) C5 0.0742(13) 0.0736(12) 0.0386(9) 0.0074(12) -0.0082(11) 0.0069(10) C6 0.0888(15) 0.0714(13) 0.0462(11) 0.0129(13) 0.0013(11) 0.0169(10) C7 0.0816(14) 0.0494(10) 0.0696(12) 0.0076(13) 0.0225(13) 0.0072(10) C8 0.0671(12) 0.0534(10) 0.0625(11) -0.0002(12) 0.0046(12) -0.0105(9) C9 0.0552(11) 0.0606(11) 0.0385(9) 0.0045(11) 0.0013(9) -0.0036(9) C10 0.0580(10) 0.0486(9) 0.0360(8) 0.0083(10) -0.0050(8) -0.0032(9) C1' 0.0675(14) 0.111(2) 0.0580(12) 0.0173(15) -0.0076(13) 0.0041(13) C2' 0.100(2) 0.103(2) 0.0701(14) 0.020(2) -0.012(2) -0.0074(13) C11 0.0550(11) 0.0531(11) 0.0455(10) 0.0000(10) 0.0073(9) 0.0078(9) C12 0.0506(11) 0.0661(12) 0.0534(11) -0.0078(11) 0.0008(10) -0.0024(10) C13 0.0489(11) 0.0717(13) 0.0631(12) 0.0017(11) 0.0063(10) 0.0004(11) C14 0.0595(12) 0.0572(11) 0.0466(10) -0.0023(12) 0.0083(10) 0.0062(10) C15 0.0648(12) 0.0602(11) 0.0639(12) -0.0101(12) -0.0017(13) 0.0030(10) C16 0.0472(11) 0.0673(12) 0.0610(12) -0.0022(11) 0.0040(10) 0.0069(10) C17 0.101(2) 0.0661(13) 0.096(2) 0.0118(15) 0.018(2) 0.0007(13) C41 0.0602(11) 0.0742(13) 0.0574(11) 0.0057(13) -0.0158(11) -0.0013(10) C42 0.0635(13) 0.0739(13) 0.0729(13) -0.0091(13) -0.0028(13) -0.0155(12) C71 0.113(2) 0.0773(14) 0.097(2) -0.009(2) 0.038(2) 0.0078(14) 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 S 0.23693(6) 0.02576(4) 0.13658(3) 0.05920(14) Uani d . 1 . S O1 -0.13811(14) -0.06105(9) 0.19123(7) 0.0656(4) Uani d . 1 . O O2 0.1778(2) 0.05657(9) 0.05573(8) 0.0767(5) Uani d . 1 . O O3 0.3578(2) 0.07726(9) 0.17582(9) 0.0745(5) Uani d . 1 . O N3 0.0952(2) 0.02133(11) 0.20293(8) 0.0514(4) Uani d . 1 . N C2 -0.0596(2) 0.02110(14) 0.16858(11) 0.0551(5) Uani d . 1 . C H2 -0.0485 0.01837 0.10628 0.066 Uiso calc R 1 . H C4 0.1146(2) 0.01360(13) 0.29912(10) 0.0537(5) Uani d . 1 . C C5 -0.0223(2) -0.06770(14) 0.42447(10) 0.0621(6) Uani d . 1 . C H5A 0.0479 -0.12061 0.42312 0.075 Uiso calc R 1 . H H5B 0.0187 -0.01978 0.46254 0.075 Uiso calc R 1 . H C6 -0.1747(2) -0.10158(14) 0.45863(11) 0.0688(7) Uani d . 1 . C H6A -0.1604 -0.12886 0.51501 0.083 Uiso calc R 1 . H H6B -0.2418 -0.04747 0.46439 0.083 Uiso calc R 1 . H C7 -0.2487(3) -0.17521(13) 0.40063(11) 0.0669(6) Uani d . 1 . C H7 -0.1841(3) -0.23172(13) 0.39889(11) 0.080 Uiso calc R 1 . H C8 -0.2608(2) -0.13429(13) 0.30957(11) 0.0610(6) Uani d . 1 . C H8A -0.2995 -0.18296 0.27153 0.073 Uiso calc R 1 . H H8B -0.3324 -0.08213 0.30969 0.073 Uiso calc R 1 . H C9 -0.1092(2) -0.09891(13) 0.27559(10) 0.0514(5) Uani d . 1 . C H9 -0.0403 -0.15312 0.27033 0.062 Uiso calc R 1 . H C10 -0.0381(2) -0.02613(13) 0.33445(9) 0.0475(5) Uani d . 1 . C H10 -0.1085 0.02743 0.33835 0.057 Uiso calc R 1 . H C1' -0.1400(3) 0.1156(2) 0.18731(12) 0.0790(8) Uani d . 1 . C H1' -0.0818 0.1703 0.18291 0.095 Uiso calc R 1 . H C2' -0.2743(3) 0.1263(2) 0.20768(13) 0.0911(9) Uani d . 1 . C H2'A -0.3374 0.0738 0.21295 0.109 Uiso calc R 1 . H H2'B -0.3121 0.1869 0.21769 0.109 Uiso calc R 1 . H C11 0.3014(2) -0.09181(13) 0.12121(11) 0.0512(6) Uani d . 1 . C C12 0.4540(2) -0.11156(14) 0.11748(11) 0.0567(6) Uani d . 1 . C H12 0.5242 -0.06328 0.12576 0.068 Uiso calc R 1 . H C13 0.5019(2) -0.20198(14) 0.10164(11) 0.0612(6) Uani d . 1 . C H13 0.6052 -0.21433 0.10040 0.073 Uiso calc R 1 . H C14 0.4029(2) -0.27517(13) 0.08752(11) 0.0544(6) Uani d . 1 . C C15 0.2489(3) -0.25471(14) 0.09044(12) 0.0630(6) Uani d . 1 . C H15 0.1792 -0.30298 0.08078 0.076 Uiso calc R 1 . H C16 0.1975(2) -0.16334(14) 0.10757(11) 0.0585(6) Uani d . 1 . C H16 0.0944 -0.15058 0.10980 0.070 Uiso calc R 1 . H C17 0.4524(3) -0.3769(2) 0.0706(2) 0.0877(9) Uani d . 1 . C C41 0.2465(2) -0.05325(14) 0.32035(12) 0.0639(6) Uani d . 1 . C C42 0.1444(2) 0.1128(2) 0.33489(14) 0.0701(7) Uani d . 1 . C C71 -0.4035(3) -0.2038(2) 0.4342(2) 0.0960(9) Uani d . 1 . C H41A 0.343(2) -0.0339(13) 0.2955(11) 0.086(6) Uiso d . 1 . H H41B 0.255(2) -0.0617(11) 0.3832(10) 0.061(5) Uiso d . 1 . H H41C 0.220(2) -0.1119(11) 0.3076(9) 0.045(5) Uiso d . 1 . H H42A 0.141(2) 0.1026(12) 0.3988(10) 0.072(6) Uiso d . 1 . H H42B 0.240(2) 0.1420(12) 0.3166(12) 0.080(6) Uiso d . 1 . H H42C 0.065(2) 0.1537(12) 0.3204(12) 0.083(6) Uiso d . 1 . H H17A 0.384(3) -0.3881(15) 0.0100(13) 0.118(8) Uiso d . 1 . H H17B 0.446(4) -0.4023(15) 0.1209(12) 0.102(8) Uiso d . 1 . H H17C 0.561(3) -0.3882(15) 0.0475(14) 0.113(8) Uiso d . 1 . H H71A -0.474(3) -0.1351(18) 0.4524(16) 0.147(10) Uiso d . 1 . H H71B -0.401(3) -0.2374(18) 0.4827(16) 0.142(10) Uiso d . 1 . H H71C -0.445(2) -0.2290(14) 0.4009(12) 0.087(7) Uiso d . 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 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 O3 S O2 119.80(9) yes O3 S N3 108.73(8) yes O2 S N3 107.02(8) yes O3 S C11 107.00(9) yes O2 S C11 106.32(8) yes N3 S C11 107.40(8) yes C2 O1 C9 116.71(13) yes C2 N3 C4 117.83(13) yes C2 N3 S 118.94(11) yes C4 N3 S 123.18(12) yes O1 C2 N3 111.86(15) yes O1 C2 C1' 116.1(2) yes N3 C2 C1' 111.0(2) yes N3 C4 C42 108.47(15) ? N3 C4 C41 110.14(14) ? C42 C4 C41 110.5(2) ? N3 C4 C10 106.16(13) yes C42 C4 C10 110.3(2) ? C41 C4 C10 111.12(15) ? C6 C5 C10 111.1(2) yes C7 C6 C5 112.6(2) yes C71 C7 C6 111.2(2) ? C71 C7 C8 110.9(2) ? C6 C7 C8 109.0(2) yes C9 C8 C7 112.5(2) yes O1 C9 C10 112.23(14) yes O1 C9 C8 106.43(15) yes C10 C9 C8 111.97(14) yes C9 C10 C5 109.75(15) yes C9 C10 C4 112.73(14) yes C5 C10 C4 112.51(15) yes C2' C1' C2 126.7(2) yes C12 C11 C16 119.8(2) ? C12 C11 S 120.70(15) ? C16 C11 S 119.34(15) ? C13 C12 C11 120.0(2) ? C12 C13 C14 122.2(2) ? C13 C14 C15 117.6(2) ? C13 C14 C17 123.5(2) ? C15 C14 C17 118.8(2) ? C16 C15 C14 121.1(2) ? C11 C16 C15 119.2(2) ? C14 C17 H17A 97.0(10) ? C14 C17 H17B 102.0(10) ? C14 C17 H17C 118.0(10) ? H17A C17 H17B 132(2) ? H17A C17 H17C 100(2) ? H17B C17 H17C 108(2) ? C4 C41 H41A 114.0(10) ? C4 C41 H41B 110.0(10) ? C4 C41 H41C 109.0(10) ? H41A C41 H41B 111(2) ? H41A C41 H41C 114(2) ? H41B C41 H41C 98.0(10) ? C4 C42 H42A 103.0(10) ? C4 C42 H42B 115.0(10) ? C4 C42 H42C 110.0(10) ? H42A C42 H42B 112(2) ? H42A C42 H42C 108(2) ? H42B C42 H42C 109(2) ? C7 C71 H71A 110.0(10) ? C7 C71 H71B 114(2) ? C7 C71 H71C 110(2) ? H71A C71 H71B 104(2) ? H71A C71 H71C 108(2) ? H71B C71 H71C 111(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 S O3 . 1.4299(14) yes S O2 . 1.4353(14) yes S N3 . 1.6281(15) yes S C11 . 1.768(2) yes O1 C2 . 1.395(2) yes O1 C9 . 1.446(2) yes N3 C2 . 1.471(2) yes N3 C4 . 1.518(2) yes C2 C1' . 1.537(3) yes C4 C42 . 1.528(3) ? C4 C41 . 1.535(3) ? C4 C10 . 1.563(3) yes C5 C6 . 1.526(3) yes C5 C10 . 1.531(2) yes C6 C7 . 1.525(3) yes C7 C71 . 1.521(4) ? C7 C8 . 1.540(3) yes C8 C9 . 1.526(3) yes C9 C10 . 1.514(2) yes C1' C2' . 1.239(3) yes C11 C12 . 1.379(3) ? C11 C16 . 1.380(3) ? C12 C13 . 1.365(3) ? C13 C14 . 1.371(3) ? C14 C15 . 1.393(3) ? C14 C17 . 1.521(3) ? C15 C16 . 1.391(3) ? C17 H17A . 1.14(2) ? C17 H17B . 0.87(2) ? C17 H17C . 1.04(2) ? C41 H41A . 0.97(2) ? C41 H41B . 0.99(2) ? C41 H41C . 0.88(2) ? C42 H42A . 1.01(2) ? C42 H42B . 0.98(2) ? C42 H42C . 0.94(2) ? C71 H71A . 1.18(2) ? C71 H71B . 0.89(2) ? C71 H71C . 0.73(2) ? 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 O3 S N3 C2 147.39(14) ? O2 S N3 C2 16.7(2) ? C11 S N3 C2 -97.15(15) ? O3 S N3 C4 -35.0(2) ? O2 S N3 C4 -165.75(14) ? C11 S N3 C4 80.4(2) ? C9 O1 C2 N3 36.7(2) yes C9 O1 C2 C1' -92.1(2) yes C4 N3 C2 O1 -58.5(2) yes S N3 C2 O1 119.20(13) yes C4 N3 C2 C1' 72.9(2) yes S N3 C2 C1' -109.34(15) yes C2 N3 C4 C42 -100.2(2) ? S N3 C4 C42 82.2(2) ? C2 N3 C4 C41 138.7(2) ? S N3 C4 C41 -38.9(2) ? C2 N3 C4 C10 18.3(2) yes S N3 C4 C10 -159.27(12) yes C10 C5 C6 C7 57.4(2) yes C5 C6 C7 C71 -177.2(2) ? C5 C6 C7 C8 -54.8(2) yes C71 C7 C8 C9 176.4(2) ? C6 C7 C8 C9 53.7(2) yes C2 O1 C9 C10 18.6(2) yes C2 O1 C9 C8 141.37(15) yes C7 C8 C9 O1 -178.82(14) yes C7 C8 C9 C10 -55.8(2) yes O1 C9 C10 C5 175.38(15) yes C8 C9 C10 C5 55.7(2) yes O1 C9 C10 C4 -58.4(2) yes C8 C9 C10 C4 -177.99(14) yes C6 C5 C10 C9 -56.3(2) yes C6 C5 C10 C4 177.3(2) yes N3 C4 C10 C9 36.9(2) yes C42 C4 C10 C9 154.2(2) ? C41 C4 C10 C9 -82.8(2) ? N3 C4 C10 C5 161.70(14) yes C42 C4 C10 C5 -81.0(2) ? C41 C4 C10 C5 42.0(2) ? O1 C2 C1' C2' -12.1(3) yes N3 C2 C1' C2' -141.3(2) yes O3 S C11 C12 -22.4(2) ? O2 S C11 C12 106.7(2) ? N3 S C11 C12 -139.04(15) ? O3 S C11 C16 161.57(14) ? O2 S C11 C16 -69.3(2) ? N3 S C11 C16 45.0(2) ? C16 C11 C12 C13 -1.0(3) ? S C11 C12 C13 -176.97(13) ? C11 C12 C13 C14 1.2(3) ? C12 C13 C14 C15 -0.5(3) ? C12 C13 C14 C17 -179.4(2) ? C13 C14 C15 C16 -0.3(3) ? C17 C14 C15 C16 178.6(2) ? C12 C11 C16 C15 0.2(3) ? S C11 C16 C15 176.21(14) ? C14 C15 C16 C11 0.5(3) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21182884 2 PubChem 15401415