Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Wei Zhuang.' 'Rita G. Hazell' 'Karl Anker Jorgensen' _publ_contact_author_name 'Karl Anker Jorgensen' _publ_contact_author_address ; Department of Chemistry Aarhus University Aarhus C DK 8000 DENMARK ; _publ_contact_author_email KAJ@CHEM.AU.DK _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Enantioselective Friedel-Crafts type addition of indoles to nitroolefins using a chiral hydrogen-bonding catalyst - synthesis of optically active tetrahydro-beta-carbolines ; #============================================================================== _publ_section_references ; Becker,P.J. & Coppens, P. (1974). Acta Cryst. A30, 129-153. Burnett,M.N. & Johnson,C.K. (1996). ORTEP-III. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Busing,W.R., Martin,K.O. & Levy,H.A. (1962). ORFLS. Report ORNL-TM-305. Oak Ridge National Laboratory, Tennessee, USA. Hazell,A. (1995). KRYSTAL, An integrated system of crystallographic programs. Aarhus University, Denmark. Rogers,D. (1981). Acta Cryst. A37, 734-741. Siemens (1995) SMART, SAINT and XPREP Area-Detector Control and Integration Software. Siemens Analytical X-ray Instruments Inc. Madison, Wisconsin, USA. ; data_04jowz002_0m _database_code_depnum_ccdc_archive 'CCDC 268882' _audit_creation_date 2005-01-24T10:45:59-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C31 H25 Cl1 N2 O1' _chemical_formula_sum 'C31 H25 Cl N2 O' _chemical_formula_weight 476.98 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'P 31' _symmetry_space_group_name_Hall 'P 31' _symmetry_Int_Tables_number 144 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+1/3' '-x+y, -x, z+2/3' _cell_length_a 10.0175(8) _cell_length_b 10.0175(8) _cell_length_c 21.2378(13) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_volume 1845.7(2) _cell_formula_units_Z 3 _cell_measurement_temperature 225(2) _cell_measurement_reflns_used 1904 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 20.57 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.08 _exptl_crystal_density_diffrn 1.287 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 750 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.182 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; R.H. Blessing, Acta Cryst. (1995), A51, 33-38 ; _exptl_absorpt_correction_T_min 0.955 _exptl_absorpt_correction_T_max 0.988 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 225(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device_type 'Bruker APEX2 CCD-based diffractometer' _diffrn_measurement_method \f-scans _diffrn_detector_area_resol_mean 0.0833 _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0486 _diffrn_reflns_av_unetI/netI 0.0764 _diffrn_reflns_number 4167 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 25.94 _diffrn_reflns_theta_full 25.94 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 4167 _reflns_number_gt 2774 _reflns_threshold_expression >2sigma(I) _diffrn_reflns_reduction_process ; Scaled and merged with SORTAV R.H. Blessing, (1987) Cryst. Rev. 1, 3-58 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397 ; #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Apex2 (Bruker-Nonius, 2004)' _computing_cell_refinement 'SAINT+ (Bruker-Nonius, 2004)' _computing_data_reduction 'SAINT+ (Bruker-Nonius, 2004)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0414P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 4167 _refine_ls_number_parameters 316 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0761 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.0905 _refine_ls_wR_factor_gt 0.0805 _refine_ls_goodness_of_fit_ref 0.962 _refine_ls_restrained_S_all 0.961 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.03(6) _refine_diff_density_max 0.139 _refine_diff_density_min -0.17 _refine_diff_density_rms 0.034 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl -0.25431(9) 0.14116(9) 0.31830(4) 0.0589(2) Uani 1 1 d . . . O1 O 0.1377(3) 0.6688(3) 0.54004(11) 0.0887(9) Uani 1 1 d . . . N1 N 0.4943(3) 1.2088(3) 0.49649(9) 0.0396(6) Uani 1 1 d . . . N2 N 0.2920(3) 0.7922(3) 0.45745(10) 0.0406(6) Uani 1 1 d . . . C1 C 0.4209(3) 1.2349(3) 0.39872(11) 0.0360(7) Uani 1 1 d . . . C2 C 0.4026(3) 1.3197(3) 0.35015(12) 0.0402(7) Uani 1 1 d . . . H2 H 0.3553 1.271 0.3121 0.048 Uiso 1 1 calc R . . C3 C 0.4538(4) 1.4731(3) 0.35842(14) 0.0456(8) Uani 1 1 d . . . H3 H 0.4414 1.5294 0.3258 0.055 Uiso 1 1 calc R . . C4 C 0.5247(4) 1.5480(4) 0.41487(14) 0.0479(8) Uani 1 1 d . . . H4 H 0.5599 1.6538 0.4194 0.057 Uiso 1 1 calc R . . C5 C 0.5431(3) 1.4687(4) 0.46354(13) 0.0431(7) Uani 1 1 d . . . H5 H 0.5903 1.5186 0.5014 0.052 Uiso 1 1 calc R . . C6 C 0.4900(3) 1.3123(3) 0.45524(12) 0.0363(7) Uani 1 1 d . . . C7 C 0.4293(3) 1.0674(3) 0.46656(12) 0.0373(7) Uani 1 1 d . . . C8 C 0.3867(3) 1.0792(3) 0.40667(12) 0.0357(7) Uani 1 1 d . . . C9 C 0.3195(3) 0.9468(3) 0.36117(12) 0.0376(7) Uani 1 1 d . . . H9 H 0.3864 0.9809 0.3234 0.045 Uiso 1 1 calc R . . C9A C 0.1588(3) 0.9020(3) 0.33923(12) 0.0391(7) Uani 1 1 d . . . C9B C 0.0551(4) 0.9162(4) 0.37710(15) 0.0522(8) Uani 1 1 d . . . H9B H 0.0842 0.9538 0.4183 0.063 Uiso 1 1 calc R . . C9C C -0.0911(4) 0.8767(4) 0.35612(18) 0.0648(10) Uani 1 1 d . . . H9C H -0.16 0.8868 0.3831 0.078 Uiso 1 1 calc R . . C9D C -0.1349(5) 0.8234(4) 0.2965(2) 0.0781(12) Uani 1 1 d . . . H9D H -0.2334 0.798 0.2819 0.094 Uiso 1 1 calc R . . C9E C -0.0337(5) 0.8070(4) 0.25766(19) 0.0788(13) Uani 1 1 d . . . H9E H -0.0641 0.769 0.2166 0.095 Uiso 1 1 calc R . . C9F C 0.1122(4) 0.8460(4) 0.27873(15) 0.0579(9) Uani 1 1 d . . . H9F H 0.1801 0.8344 0.2518 0.069 Uiso 1 1 calc R . . C10 C 0.3317(3) 0.8130(3) 0.38998(12) 0.0409(7) Uani 1 1 d . . . H10A H 0.2623 0.7178 0.3674 0.049 Uiso 1 1 calc R . . H10B H 0.4371 0.8326 0.3846 0.049 Uiso 1 1 calc R . . C11 C 0.4004(3) 0.9216(3) 0.49791(12) 0.0405(7) Uani 1 1 d . . . H11 H 0.3471 0.9133 0.5382 0.049 Uiso 1 1 calc R . . C11A C 0.5429(4) 0.9093(3) 0.51288(12) 0.0413(7) Uani 1 1 d . . . C11B C 0.6888(4) 1.0179(4) 0.49245(14) 0.0546(9) Uani 1 1 d . . . H11B H 0.7026 1.1013 0.4674 0.065 Uiso 1 1 calc R . . C11C C 0.8144(4) 1.0029(5) 0.50918(16) 0.0671(10) Uani 1 1 d . . . H11C H 0.9134 1.0767 0.4953 0.081 Uiso 1 1 calc R . . C11D C 0.7963(5) 0.8822(5) 0.54552(16) 0.0677(11) Uani 1 1 d . . . H11D H 0.8823 0.8733 0.5567 0.081 Uiso 1 1 calc R . . C11E C 0.6518(5) 0.7743(4) 0.56553(15) 0.0612(10) Uani 1 1 d . . . H11E H 0.6389 0.6911 0.5905 0.073 Uiso 1 1 calc R . . C11F C 0.5249(4) 0.7870(4) 0.54932(13) 0.0510(8) Uani 1 1 d . . . H11F H 0.4262 0.7122 0.5631 0.061 Uiso 1 1 calc R . . C12 C 0.1659(4) 0.6729(4) 0.48344(14) 0.0535(9) Uani 1 1 d . . . C13 C 0.0621(4) 0.5406(4) 0.44138(14) 0.0488(8) Uani 1 1 d . . . C14 C -0.0759(4) 0.5257(4) 0.42095(14) 0.0526(8) Uani 1 1 d . . . H14 H -0.1034 0.5992 0.4326 0.063 Uiso 1 1 calc R . . C15 C -0.1734(4) 0.4022(4) 0.38324(15) 0.0516(8) Uani 1 1 d . . . H15 H -0.2667 0.3922 0.3688 0.062 Uiso 1 1 calc R . . C16 C -0.1328(4) 0.2937(3) 0.36690(13) 0.0457(8) Uani 1 1 d . . . C17 C 0.0031(4) 0.3058(4) 0.38765(14) 0.0506(8) Uani 1 1 d . . . H17 H 0.0296 0.231 0.3767 0.061 Uiso 1 1 calc R . . C18 C 0.0999(4) 0.4306(4) 0.42493(14) 0.0526(8) Uani 1 1 d . . . H18 H 0.1932 0.4404 0.4393 0.063 Uiso 1 1 calc R . . C20 C 0.5663(4) 1.2486(4) 0.55832(13) 0.0542(9) Uani 1 1 d . . . H20A H 0.5338 1.1553 0.5826 0.081 Uiso 1 1 calc R . . H20B H 0.5355 1.3142 0.58 0.081 Uiso 1 1 calc R . . H20C H 0.6775 1.3029 0.5536 0.081 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0481(5) 0.0565(5) 0.0608(5) -0.0019(4) 0.0011(4) 0.0177(5) O1 0.0792(19) 0.087(2) 0.0499(15) -0.0021(14) 0.0239(13) 0.0044(16) N1 0.0444(15) 0.0417(15) 0.0358(12) -0.0071(11) -0.0066(11) 0.0237(12) N2 0.0426(15) 0.0394(15) 0.0376(13) 0.0026(11) 0.0048(11) 0.0188(13) C1 0.0295(15) 0.0402(18) 0.0349(15) 0.0016(13) 0.0017(12) 0.0148(14) C2 0.0377(17) 0.0453(19) 0.0340(15) -0.0010(14) -0.0028(13) 0.0179(15) C3 0.0481(19) 0.045(2) 0.0480(17) 0.0087(16) 0.0042(15) 0.0263(17) C4 0.047(2) 0.0373(18) 0.0553(19) -0.0031(15) 0.0004(16) 0.0184(15) C5 0.0413(18) 0.0438(19) 0.0407(15) -0.0040(14) -0.0041(14) 0.0187(15) C6 0.0317(16) 0.0390(18) 0.0375(15) -0.0055(13) -0.0011(13) 0.0171(14) C7 0.0351(17) 0.0417(18) 0.0363(14) -0.0040(14) -0.0023(13) 0.0202(15) C8 0.0314(16) 0.0374(17) 0.0365(15) -0.0026(13) -0.0003(13) 0.0159(14) C9 0.0360(17) 0.0383(16) 0.0335(14) -0.0033(13) 0.0008(13) 0.0147(14) C9A 0.0425(18) 0.0305(16) 0.0371(15) -0.0002(13) -0.0052(14) 0.0128(15) C9B 0.047(2) 0.053(2) 0.0530(18) -0.0042(16) -0.0067(16) 0.0217(18) C9C 0.046(2) 0.057(2) 0.090(3) -0.006(2) -0.0130(19) 0.0239(18) C9D 0.056(3) 0.062(3) 0.106(3) -0.002(2) -0.035(2) 0.022(2) C9E 0.081(3) 0.065(3) 0.064(2) -0.014(2) -0.040(2) 0.017(2) C9F 0.061(2) 0.050(2) 0.0503(19) -0.0076(16) -0.0133(17) 0.0183(18) C10 0.0423(17) 0.0399(17) 0.0404(16) -0.0030(13) 0.0058(13) 0.0206(15) C11 0.0425(18) 0.0436(18) 0.0322(14) -0.0032(13) 0.0000(13) 0.0190(15) C11A 0.052(2) 0.0467(19) 0.0292(14) -0.0047(13) -0.0065(14) 0.0281(16) C11B 0.055(2) 0.074(2) 0.0454(18) 0.0120(17) 0.0009(16) 0.041(2) C11C 0.058(2) 0.090(3) 0.063(2) 0.008(2) -0.0003(18) 0.045(2) C11D 0.082(3) 0.091(3) 0.058(2) -0.018(2) -0.027(2) 0.065(3) C11E 0.093(3) 0.059(2) 0.0470(19) -0.0120(17) -0.025(2) 0.050(2) C11F 0.070(2) 0.048(2) 0.0401(16) -0.0069(15) -0.0116(16) 0.0334(18) C12 0.043(2) 0.056(2) 0.052(2) 0.0025(17) 0.0100(16) 0.0173(17) C13 0.0414(19) 0.048(2) 0.0476(18) 0.0081(15) 0.0131(15) 0.0150(17) C14 0.047(2) 0.048(2) 0.063(2) 0.0011(17) 0.0074(17) 0.0239(17) C15 0.0401(19) 0.058(2) 0.0567(18) 0.0106(17) 0.0089(16) 0.0248(18) C16 0.0396(18) 0.0443(19) 0.0454(17) 0.0058(14) 0.0053(14) 0.0151(16) C17 0.050(2) 0.050(2) 0.0550(19) 0.0039(16) 0.0046(16) 0.0270(17) C18 0.042(2) 0.057(2) 0.061(2) 0.0033(17) 0.0019(16) 0.0267(18) C20 0.065(2) 0.057(2) 0.0401(16) -0.0105(16) -0.0172(16) 0.0304(19) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C16 1.738(3) . ? O1 C12 1.231(3) . ? N1 C6 1.374(4) . ? N1 C7 1.383(3) . ? N1 C20 1.455(3) . ? N2 C12 1.349(4) . ? N2 C10 1.474(3) . ? N2 C11 1.480(3) . ? C1 C2 1.405(4) . ? C1 C6 1.408(4) . ? C1 C8 1.429(4) . ? C2 C3 1.366(4) . ? C2 H2 0.94 . ? C3 C4 1.404(4) . ? C3 H3 0.94 . ? C4 C5 1.371(4) . ? C4 H4 0.94 . ? C5 C6 1.392(4) . ? C5 H5 0.94 . ? C7 C8 1.366(4) . ? C7 C11 1.496(4) . ? C8 C9 1.501(4) . ? C9 C9A 1.512(4) . ? C9 C10 1.533(4) . ? C9 H9 0.99 . ? C9A C9B 1.377(4) . ? C9A C9F 1.386(4) . ? C9B C9C 1.386(5) . ? C9B H9B 0.94 . ? C9C C9D 1.358(5) . ? C9C H9C 0.94 . ? C9D C9E 1.379(6) . ? C9D H9D 0.94 . ? C9E C9F 1.385(5) . ? C9E H9E 0.94 . ? C9F H9F 0.94 . ? C10 H10A 0.98 . ? C10 H10B 0.98 . ? C11 C11A 1.527(4) . ? C11 H11 0.99 . ? C11A C11F 1.383(4) . ? C11A C11B 1.385(4) . ? C11B C11C 1.386(4) . ? C11B H11B 0.94 . ? C11C C11D 1.368(5) . ? C11C H11C 0.94 . ? C11D C11E 1.371(5) . ? C11D H11D 0.94 . ? C11E C11F 1.382(5) . ? C11E H11E 0.94 . ? C11F H11F 0.94 . ? C12 C13 1.503(5) . ? C13 C18 1.377(5) . ? C13 C14 1.384(4) . ? C14 C15 1.385(4) . ? C14 H14 0.94 . ? C15 C16 1.382(4) . ? C15 H15 0.94 . ? C16 C17 1.377(4) . ? C17 C18 1.384(4) . ? C17 H17 0.94 . ? C18 H18 0.94 . ? C20 H20A 0.97 . ? C20 H20B 0.97 . ? C20 H20C 0.97 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 N1 C7 107.7(2) . . ? C6 N1 C20 124.5(2) . . ? C7 N1 C20 127.6(3) . . ? C12 N2 C10 126.2(2) . . ? C12 N2 C11 119.4(2) . . ? C10 N2 C11 114.4(2) . . ? C2 C1 C6 118.0(3) . . ? C2 C1 C8 135.5(2) . . ? C6 C1 C8 106.5(2) . . ? C3 C2 C1 119.7(3) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C2 C3 C4 121.1(3) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 120.9(3) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C4 C5 C6 118.0(3) . . ? C4 C5 H5 121 . . ? C6 C5 H5 121 . . ? N1 C6 C5 129.1(2) . . ? N1 C6 C1 108.7(2) . . ? C5 C6 C1 122.3(3) . . ? C8 C7 N1 110.3(3) . . ? C8 C7 C11 125.7(2) . . ? N1 C7 C11 123.9(2) . . ? C7 C8 C1 106.8(2) . . ? C7 C8 C9 123.0(3) . . ? C1 C8 C9 130.2(2) . . ? C8 C9 C9A 113.7(2) . . ? C8 C9 C10 108.6(2) . . ? C9A C9 C10 113.7(2) . . ? C8 C9 H9 106.8 . . ? C9A C9 H9 106.8 . . ? C10 C9 H9 106.8 . . ? C9B C9A C9F 117.7(3) . . ? C9B C9A C9 122.4(2) . . ? C9F C9A C9 120.0(3) . . ? C9A C9B C9C 121.8(3) . . ? C9A C9B H9B 119.1 . . ? C9C C9B H9B 119.1 . . ? C9D C9C C9B 120.0(4) . . ? C9D C9C H9C 120 . . ? C9B C9C H9C 120 . . ? C9C C9D C9E 119.5(4) . . ? C9C C9D H9D 120.3 . . ? C9E C9D H9D 120.3 . . ? C9D C9E C9F 120.5(3) . . ? C9D C9E H9E 119.7 . . ? C9F C9E H9E 119.7 . . ? C9E C9F C9A 120.6(4) . . ? C9E C9F H9F 119.7 . . ? C9A C9F H9F 119.7 . . ? N2 C10 C9 112.2(2) . . ? N2 C10 H10A 109.2 . . ? C9 C10 H10A 109.2 . . ? N2 C10 H10B 109.2 . . ? C9 C10 H10B 109.2 . . ? H10A C10 H10B 107.9 . . ? N2 C11 C7 107.2(2) . . ? N2 C11 C11A 110.9(2) . . ? C7 C11 C11A 116.0(2) . . ? N2 C11 H11 107.5 . . ? C7 C11 H11 107.5 . . ? C11A C11 H11 107.5 . . ? C11F C11A C11B 119.3(3) . . ? C11F C11A C11 118.4(3) . . ? C11B C11A C11 122.3(3) . . ? C11A C11B C11C 119.6(3) . . ? C11A C11B H11B 120.2 . . ? C11C C11B H11B 120.2 . . ? C11D C11C C11B 120.9(4) . . ? C11D C11C H11C 119.5 . . ? C11B C11C H11C 119.5 . . ? C11C C11D C11E 119.5(3) . . ? C11C C11D H11D 120.2 . . ? C11E C11D H11D 120.2 . . ? C11D C11E C11F 120.5(3) . . ? C11D C11E H11E 119.8 . . ? C11F C11E H11E 119.8 . . ? C11E C11F C11A 120.2(3) . . ? C11E C11F H11F 119.9 . . ? C11A C11F H11F 119.9 . . ? O1 C12 N2 121.8(3) . . ? O1 C12 C13 120.3(3) . . ? N2 C12 C13 117.8(3) . . ? C18 C13 C14 119.6(3) . . ? C18 C13 C12 120.7(3) . . ? C14 C13 C12 119.7(3) . . ? C13 C14 C15 119.9(3) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C16 C15 C14 119.6(3) . . ? C16 C15 H15 120.2 . . ? C14 C15 H15 120.2 . . ? C17 C16 C15 121.1(3) . . ? C17 C16 Cl1 119.6(3) . . ? C15 C16 Cl1 119.2(3) . . ? C16 C17 C18 118.5(3) . . ? C16 C17 H17 120.7 . . ? C18 C17 H17 120.7 . . ? C13 C18 C17 121.3(3) . . ? C13 C18 H18 119.4 . . ? C17 C18 H18 119.4 . . ? N1 C20 H20A 109.5 . . ? N1 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N1 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 1.1(4) . . . . ? C8 C1 C2 C3 -178.3(3) . . . . ? C1 C2 C3 C4 -0.1(4) . . . . ? C2 C3 C4 C5 -0.6(5) . . . . ? C3 C4 C5 C6 0.2(4) . . . . ? C7 N1 C6 C5 -179.2(3) . . . . ? C20 N1 C6 C5 -3.5(5) . . . . ? C7 N1 C6 C1 0.2(3) . . . . ? C20 N1 C6 C1 175.9(3) . . . . ? C4 C5 C6 N1 -179.7(3) . . . . ? C4 C5 C6 C1 1.0(4) . . . . ? C2 C1 C6 N1 178.9(2) . . . . ? C8 C1 C6 N1 -1.5(3) . . . . ? C2 C1 C6 C5 -1.6(4) . . . . ? C8 C1 C6 C5 177.9(3) . . . . ? C6 N1 C7 C8 1.3(3) . . . . ? C20 N1 C7 C8 -174.3(3) . . . . ? C6 N1 C7 C11 -174.5(3) . . . . ? C20 N1 C7 C11 9.9(4) . . . . ? N1 C7 C8 C1 -2.2(3) . . . . ? C11 C7 C8 C1 173.5(3) . . . . ? N1 C7 C8 C9 177.0(2) . . . . ? C11 C7 C8 C9 -7.3(4) . . . . ? C2 C1 C8 C7 -178.3(3) . . . . ? C6 C1 C8 C7 2.3(3) . . . . ? C2 C1 C8 C9 2.5(5) . . . . ? C6 C1 C8 C9 -176.9(3) . . . . ? C7 C8 C9 C9A 119.3(3) . . . . ? C1 C8 C9 C9A -61.7(4) . . . . ? C7 C8 C9 C10 -8.3(4) . . . . ? C1 C8 C9 C10 170.7(3) . . . . ? C8 C9 C9A C9B -32.2(4) . . . . ? C10 C9 C9A C9B 92.7(3) . . . . ? C8 C9 C9A C9F 147.0(3) . . . . ? C10 C9 C9A C9F -88.1(3) . . . . ? C9F C9A C9B C9C -0.1(4) . . . . ? C9 C9A C9B C9C 179.1(3) . . . . ? C9A C9B C9C C9D -0.5(5) . . . . ? C9B C9C C9D C9E 1.0(6) . . . . ? C9C C9D C9E C9F -0.8(6) . . . . ? C9D C9E C9F C9A 0.1(6) . . . . ? C9B C9A C9F C9E 0.4(5) . . . . ? C9 C9A C9F C9E -178.9(3) . . . . ? C12 N2 C10 C9 110.8(3) . . . . ? C11 N2 C10 C9 -65.8(3) . . . . ? C8 C9 C10 N2 42.1(3) . . . . ? C9A C9 C10 N2 -85.5(3) . . . . ? C12 N2 C11 C7 -130.5(3) . . . . ? C10 N2 C11 C7 46.3(3) . . . . ? C12 N2 C11 C11A 101.9(3) . . . . ? C10 N2 C11 C11A -81.2(3) . . . . ? C8 C7 C11 N2 -11.0(4) . . . . ? N1 C7 C11 N2 164.1(2) . . . . ? C8 C7 C11 C11A 113.5(3) . . . . ? N1 C7 C11 C11A -71.4(3) . . . . ? N2 C11 C11A C11F -66.0(3) . . . . ? C7 C11 C11A C11F 171.4(2) . . . . ? N2 C11 C11A C11B 115.5(3) . . . . ? C7 C11 C11A C11B -7.1(4) . . . . ? C11F C11A C11B C11C -0.5(4) . . . . ? C11 C11A C11B C11C 178.1(3) . . . . ? C11A C11B C11C C11D 0.1(5) . . . . ? C11B C11C C11D C11E 0.2(5) . . . . ? C11C C11D C11E C11F -0.1(5) . . . . ? C11D C11E C11F C11A -0.3(5) . . . . ? C11B C11A C11F C11E 0.6(4) . . . . ? C11 C11A C11F C11E -178.0(3) . . . . ? C10 N2 C12 O1 -176.1(3) . . . . ? C11 N2 C12 O1 0.3(5) . . . . ? C10 N2 C12 C13 6.1(4) . . . . ? C11 N2 C12 C13 -177.5(3) . . . . ? O1 C12 C13 C18 -98.8(4) . . . . ? N2 C12 C13 C18 79.1(4) . . . . ? O1 C12 C13 C14 78.7(4) . . . . ? N2 C12 C13 C14 -103.5(3) . . . . ? C18 C13 C14 C15 -1.2(4) . . . . ? C12 C13 C14 C15 -178.7(3) . . . . ? C13 C14 C15 C16 0.8(4) . . . . ? C14 C15 C16 C17 0.2(4) . . . . ? C14 C15 C16 Cl1 -178.8(2) . . . . ? C15 C16 C17 C18 -0.7(4) . . . . ? Cl1 C16 C17 C18 178.3(2) . . . . ? C14 C13 C18 C17 0.7(5) . . . . ? C12 C13 C18 C17 178.2(3) . . . . ? C16 C17 C18 C13 0.2(4) . . . . ? #============================================================================== data_wei-4b _database_code_depnum_ccdc_archive 'CCDC 270611' #=================================== # 5. CHEMICAL DATA _chemical_name_systematic ; (R,R) N-(1-tert-Butyl-3,3-dimethyl-2-trifluoromethanesulfonylamino-butyl)- C,C,C-trifluoro-methanesulfonamide ; _chemical_name_common ? _chemical_formula_sum 'C12 H22 F6 N2 O4 S2' _chemical_formula_moiety 'C12 H22 F6 N2 O4 S2' _chemical_formula_weight 436.46 _chemical_melting_point ? _chemical_compound_source ? #=================================== # 6. CRYSTAL DATA _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'P 41 2 2' _symmetry_space_group_name_Hall 'P 4w 2c' loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z -x,-y,1/2+z -y,+x,1/4+z +y,-x,3/4+z -x,+y,-z +x,-y,1/2-z +y,+x,3/4-z -y,-x,1/4-z _cell_length_a 12.2564(3) _cell_length_b 12.2564(3) _cell_length_c 13.4713(6) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2023.65(11) _cell_formula_units_Z 4 _cell_measurement_temperature 100 _cell_measurement_reflns_used 7356 _cell_measurement_theta_min 2.79 _cell_measurement_theta_max 34.65 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.433 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 0.335 _exptl_absorpt_correction_type none _exptl_absorpt_process_details none #=================================== # 7. EXPERIMENTAL DATA _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'x-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens SMART CCD diffractometer' _diffrn_measurement_method 'scans with narrow frames ' _diffrn_standards_decay_% 0 _diffrn_reflns_number 61260 _diffrn_reflns_av_R_equivalents 0.064 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 34.65 _diffrn_reflns_reduction_process 61260 _reflns_number_total 4269 _diffrn_measured_fraction_theta_max 0.93 _diffrn_measured_fraction_theta_full 0.984 _diffrn_reflns_theta_full 30.51 _reflns_number_gt 3636 _reflns_threshold_expression I>3\s(I) _computing_data_collection 'SMART (Siemens, 1995)' _computing_cell_refinement 'SAINT (Siemens, 1995)' _computing_data_reduction 'SAINT (Siemens, 1995)' _computing_structure_solution ; SIR97 (Altomare et al., 1997 ), KRYSTAL ; _computing_structure_refinement 'modified ORFLS(1962), KRYSTAL' _computing_molecular_graphics ; ORTEP-III (Burnett & Johnson, 1996), KRYSTAL ; _computing_publication_material KRYSTAL _atom_type_scat_source IntTabIV #=================================== # 8. REFINEMENT DATA _refine_special_details ; The hydrogen atom on Nitrogen was located from a difference map but not refined. The fluorine atoms have large displacement parameters and the large peaks and holes in the final difference map are in this region, hinting at some degree of disorder here. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w = 1/{[s~cs~(F^2^)+0.05F^2^]}^2^ ; _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method ; Type 1 Lorentzian isotropic (Becker and Coppens, 1974) ; _refine_ls_extinction_coef 85(23) _refine_ls_abs_structure_details ; The least squares refinement included a factor according to Rogers (1981). 3636 significant reflections were used, including 1466 Bijvoet pairs. ; _refine_ls_abs_structure_Rogers 0.89(13) _refine_ls_number_reflns 3636 _refine_ls_number_parameters 120 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_gt 0.044 _refine_ls_wR_factor_ref 0.093 _refine_ls_goodness_of_fit_ref 0.904 _refine_ls_shift/su_max 0.0046 _refine_ls_shift/su_mean 0.0005 _refine_diff_density_max 1.24(11) _refine_diff_density_min -0.76(11) #========================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS 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 S1 0.44253(3) 0.20938(3) 0.30154(3) 0.0167(2) Uij F1 0.53820(20) 0.38803(15) 0.35467(18) 0.0923(16) Uij F2 0.64761(11) 0.26942(15) 0.30581(17) 0.0748(12) Uij F3 0.54954(14) 0.35317(17) 0.20196(13) 0.0784(12) Uij O1 0.34747(10) 0.27013(11) 0.27468(9) 0.0259(6) Uij O2 0.47792(12) 0.11871(11) 0.24412(9) 0.0290(7) Uij N1 0.44164(11) 0.17909(10) 0.41710(9) 0.0167(5) Uij C1 0.5520(2) 0.3105(2) 0.2901(1) 0.0307(9) Uij C2 0.4566(1) 0.0672(1) 0.4574(1) 0.0163(6) Uij C3 0.3442(1) 0.0155(1) 0.4861(1) 0.0209(7) Uij C4 0.2913(2) 0.0733(1) 0.5744(1) 0.0272(8) Uij C5 0.3616(2) -0.1054(1) 0.5127(1) 0.0293(9) Uij C6 0.2677(2) 0.0197(2) 0.3963(1) 0.0298(9) Uij H1n 0.4096 0.2209 0.4530 0.0200 Uiso H2 0.4857 0.0241 0.4051 0.0196 Uiso H4a 0.2231 0.0418 0.5918 0.0326 Uiso H4b 0.2802 0.1477 0.5577 0.0326 Uiso H4c 0.3389 0.0685 0.6298 0.0326 Uiso H5a 0.2934 -0.1368 0.5301 0.0352 Uiso H5b 0.4104 -0.1109 0.5672 0.0352 Uiso H5c 0.3912 -0.1429 0.4571 0.0352 Uiso H6a 0.1994 -0.0117 0.4137 0.0358 Uiso H6b 0.2989 -0.0200 0.3428 1.5306 Uiso H6c 0.2571 0.0935 0.3767 1.5306 Uiso 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 0.0198(2) 0.0190(2) 0.0112(1) -0.0001(1) 0.0005(1) 0.0008(1) F1 0.1122(18) 0.0520(10) 0.1127(18) -0.0520(12) 0.0245(16) -0.0300(11) F2 0.0236(6) 0.0702(11) 0.1306(17) -0.0098(6) -0.0091(8) 0.0616(12) F3 0.0542(9) 0.1150(15) 0.0659(10) -0.0412(10) -0.0235(8) 0.0743(11) O1 0.0222(5) 0.0385(7) 0.0172(6) 0.0044(5) -0.0011(4) 0.0069(5) O2 0.0479(8) 0.0255(6) 0.0135(6) 0.0045(6) 0.0065(5) -0.0037(4) N1 0.0245(6) 0.0149(5) 0.0107(5) 0.0021(5) 0.0024(5) 0.0006(4) C1 0.0284(8) 0.0312(9) 0.0326(9) -0.0066(7) -0.0055(7) 0.0165(7) C2 0.0224(6) 0.0128(5) 0.0137(6) -0.0006(5) 0.0011(5) 0.0001(5) C3 0.0251(7) 0.0200(7) 0.0175(7) -0.0062(5) 0.0013(6) 0.0007(5) C4 0.0280(8) 0.0301(8) 0.0234(8) -0.0059(7) 0.0077(6) -0.0003(6) C5 0.0417(10) 0.0193(7) 0.0269(9) -0.0107(7) 0.0002(7) 0.0025(6) C6 0.0268(9) 0.0350(9) 0.0277(9) -0.0091(7) -0.0023(7) 0.0021(7) #================================= # 10. MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 S1 O2 1.422(1) . . S1 O1 1.429(1) . . S1 N1 1.600(1) . . S1 C1 1.833(2) . . F1 C1 1.299(3) . . F2 C1 1.293(2) . . F3 C1 1.298(2) . . N1 C2 1.486(2) . . C2 C2 1.564(3) . 5_656 C2 C3 1.565(2) . . C3 C4 1.529(2) . . C3 C6 1.533(2) . . C3 C5 1.538(2) . . N1 H1n 0.81 . . C2 H2 0.95 . . C4 H4b 0.95 . . C4 H4c 0.95 . . C4 H4a 0.95 . . C5 H5b 0.95 . . C5 H5a 0.95 . . C5 H5c 0.95 . . C6 H6b 0.95 . . C6 H6a 0.95 . . C6 H6c 0.95 . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 O1 S1 O2 121.21(9) . . . N1 S1 O2 110.49(7) . . . C1 S1 O2 105.04(9) . . . N1 S1 O1 111.19(7) . . . C1 S1 O1 102.89(8) . . . C1 S1 N1 104.10(8) . . . S1 N1 C2 124.6(1) . . . F3 C1 F2 109.1(2) . . . F1 C1 F2 107.0(2) . . . S1 C1 F2 112.7(1) . . . F1 C1 F3 108.3(2) . . . S1 C1 F3 109.4(1) . . . S1 C1 F1 110.1(2) . . . C2 C2 N1 110.61(8) 5_656 . . C3 C2 N1 110.8(1) . . . C3 C2 C2 114.6(1) . . 5_656 C6 C3 C4 109.8(2) . . . C5 C3 C4 108.9(1) . . . C2 C3 C4 112.2(1) . . . C5 C3 C6 107.5(1) . . . C2 C3 C6 109.3(1) . . . C2 C3 C5 109.1(1) . . . C2 N1 H1n 115.3 . . . S1 N1 H1n 116.1 . . . N1 C2 H2 106.8 . . . C2 C2 H2 106.8 5_656 . . C3 C2 H2 106.8 . . . H4c C4 H4b 109.5 . . . H4a C4 H4b 108.8 . . . C3 C4 H4b 108.8 . . . H4a C4 H4c 108.8 . . . C3 C4 H4c 108.8 . . . C3 C4 H4a 112.2 . . . H5a C5 H5b 109.6 . . . H5c C5 H5b 109.5 . . . C3 C5 H5b 109.6 . . . H5c C5 H5a 109.6 . . . C3 C5 H5a 109.1 . . . C3 C5 H5c 109.6 . . . H6a C6 H6b 109.5 . . . H6c C6 H6b 109.5 . . . C3 C6 H6b 109.6 . . . H6c C6 H6a 109.5 . . . C3 C6 H6a 109.3 . . . C3 C6 H6c 109.5 . . . loop_ _publ_manuscript_incl_extra_item '_geom_bond_atom_site_label_D' '_geom_bond_atom_site_label_H' '_geom_contact_atom_site_label_A' '_geom_bond_distance_DH' '_geom_contact_distance_HA' '_geom_contact_distance_DA' '_geom_angle_DHA' '_geom_contact_site_symmetry_A' loop_ _geom_bond_atom_site_label_D _geom_bond_atom_site_label_H _geom_contact_atom_site_label_A _geom_bond_distance_DH _geom_contact_distance_HA _geom_contact_distance_DA _geom_angle_DHA _geom_contact_site_symmetry_A N1 H1n O1 0.807 2.328 3.048(2) 149.1(1) 7_555 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 N1 C2 C2 N1 19.4(2) . . 5_656 5_656 S1 N1 C2 C2 131.4(1) . . . 5_656 # Dihedral angle: # S1 N1 C2 - S1 N1 C2 162.8(2) . . . 5_656 # Intramolecular distances: # N1 N1 2.652(3) . 5_656 # H1n H1n 2.552(0) . 5_656 # N1 H1n 2.578(1) . 5_656 # H1n H2 3.333(0) . 5_656 # H2 H2 2.581(0) . 5_656 # S1 S1 5.530(1) . 5_656 data_wei-4c _database_code_depnum_ccdc_archive 'CCDC 270612' #=================================== # 5. CHEMICAL DATA _chemical_name_systematic ; (R,R) N-(1,2-Dicyclohexyl-2-trifluoromethanesulfonylamino-ethyl9- C,C,C-trifluoro-methanesulfonamide ; _chemical_formula_sum 'C16 H26 F6 N2 O4 S2' _chemical_formula_moiety 'C16 H26 F6 N2 O4 S2' _chemical_formula_weight 488.53 #=================================== # 6. CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z -x,+y,1/2-z -x,-y,-z +x,-y,1/2+z 1/2+x,1/2+y,+z 1/2-x,1/2+y,1/2-z 1/2-x,1/2-y,-z 1/2+x,1/2-y,1/2+z _cell_length_a 20.6214(6) _cell_length_b 10.7987(7) _cell_length_c 9.401(3) _cell_angle_alpha 90.000 _cell_angle_beta 95.972(3) _cell_angle_gamma 90.000 _cell_volume 2082.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100 _cell_measurement_reflns_used 8505 _cell_measurement_theta_min 2.97 _cell_measurement_theta_max 33.94 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.559 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 0.335 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, 1996 ' _exptl_absorpt_correction_T_min 0.773 _exptl_absorpt_correction_T_max 1.000 #=================================== # 7. EXPERIMENTAL DATA _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'x-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens SMART CCD diffractometer' _diffrn_measurement_method 'scans with narrow frames' _diffrn_standards_decay_% 0 _diffrn_reflns_number 33027 _diffrn_reflns_av_R_equivalents 0.109 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 33.94 _diffrn_reflns_reduction_process 33027 _reflns_number_total 4126 _diffrn_measured_fraction_theta_max 0.933 _diffrn_measured_fraction_theta_full 0.990 _diffrn_reflns_theta_full 33.94 _reflns_number_gt 2968 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Siemens, 1995)' _computing_cell_refinement 'SAINT (Siemens, 1995)' _computing_data_reduction 'SAINT (Siemens, 1995)' _computing_structure_solution ; SIR97 (Altomare et al., 1997 ), KRYSTAL ; _computing_structure_refinement 'modified ORFLS(1962), KRYSTAL' _computing_molecular_graphics ; ORTEP-III (Burnett & Johnson, 1996), KRYSTAL ; _computing_publication_material KRYSTAL _atom_type_scat_source IntTabIV #=================================== # 8. REFINEMENT DATA _refine_special_details ; The structure consists of layers in the bc-plane with very little interaction between layers resulting in serious disorder in the stacking of planes. Many lines in reciporcal space parallel to the a-axis are continuous lines with few spots and gaps. Datasets from several crystals have been collected showing varying degrees of twinning. Structure solution in various space groups all agree on the same structure for one layer. The present solution neglects some streaks with weak maxima but accounts reasonably for most of the data; the agreement was improved by giving separate scalefactors to reflections on lines with continuous streaks and to h0l, which is common to two twins. The final difference map shows maxima and minima in the region of the cyclo- hexane rings, but it was not possible to fit them to a model for an alternative orientation of the ring, and it is consireded most likely an effect of neglect of twin-contributions to many reflections. Another crystal had its strong reflections indexed on a triclinic cell with a = 9.432(2), b = 10.891(3), c = 11.339(3), \a = 104.54, \b = 109.09(2), \c = 90.05(2). The disorder-streaks had less well defined maxima. It solved in space group P -1 to give the same structure within the layer but a different stacking of layers. The refinement was less satisfactory, possibly because the influence of twinning and other stackings disorders were neglected. ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w= 1/{[\s~cs~(F^2^)+B+(1+A)F^2^]^1/2^- |F|}^2^ where A = 0.10 and B = 5.0 ; _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 2968 _refine_ls_number_parameters 141 _refine_ls_number_restraints 0 _refine_ls_number_constraints 2 _refine_ls_R_factor_gt 0.143 _refine_ls_wR_factor_ref 0.169 _refine_ls_goodness_of_fit_ref 1.166 _refine_ls_shift/su_max 0.0006 _refine_ls_shift/su_mean 0.0001 _refine_diff_density_max 2.9(1) _refine_diff_density_min -1.3(1) #========================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS 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 S 0.06927(7) 0.3352(1) 0.4832(1) 0.0155(6) Uij F1 0.1777(2) 0.2910(5) 0.6464(5) 0.042(3) Uij F2 0.1498(3) 0.4798(5) 0.6387(5) 0.048(3) Uij F3 0.1888(2) 0.3946(5) 0.4581(4) 0.038(2) Uij O1 0.0764(2) 0.2118(4) 0.4303(5) 0.023(2) Uij O2 0.0515(2) 0.4365(4) 0.3890(5) 0.025(2) Uij N 0.0253(2) 0.3357(4) 0.6131(5) 0.016(2) Uij C1 -0.0056(2) 0.2238(5) 0.6677(5) 0.013(2) Uij C2 -0.0776(3) 0.2145(5) 0.6081(6) 0.016(2) Uij C3 -0.1101(3) 0.1006(6) 0.6624(6) 0.020(3) Uij C4 -0.1817(3) 0.0883(7) 0.6018(6) 0.026(3) Uij C5 -0.1900(3) 0.0925(7) 0.4380(7) 0.028(3) Uij C6 -0.1573(3) 0.2066(7) 0.3839(6) 0.027(3) Uij C7 -0.0862(3) 0.2153(6) 0.4433(6) 0.022(3) Uij C8 0.1511(3) 0.3793(6) 0.5627(6) 0.023(3) Uij H1n 0.0032 0.4002 0.6122 0.019 Uiso H1 0.0162 0.1537 0.6346 0.016 Uiso H2 -0.0995 0.2851 0.6400 0.019 Uiso H3a -0.1079 0.1053 0.7637 0.024 Uiso H3b -0.0871 0.0294 0.6359 0.024 Uiso H4a -0.2058 0.1544 0.6374 0.032 Uiso H4b -0.1981 0.0116 0.6323 0.032 Uiso H5a -0.2352 0.0945 0.4054 0.034 Uiso H5b -0.1709 0.0206 0.4018 0.034 Uiso H6a -0.1796 0.2782 0.4121 0.032 Uiso H6b -0.1599 0.2031 0.2825 0.032 Uiso H7a -0.0634 0.1467 0.4095 0.027 Uiso H7b -0.0685 0.2900 0.4105 0.027 Uiso 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 0.0171(6) 0.0161(7) 0.0137(5) -0.0001(5) 0.0040(4) 0.0025(5) F1 0.030(2) 0.053(3) 0.040(2) 0.000(2) -0.005(2) 0.023(2) F2 0.056(3) 0.047(3) 0.041(3) -0.031(2) 0.005(2) -0.014(2) F3 0.017(2) 0.069(3) 0.029(2) -0.009(2) 0.008(1) 0.010(2) O1 0.030(2) 0.024(2) 0.018(2) 0.002(2) 0.011(2) -0.004(2) O2 0.033(2) 0.021(2) 0.022(2) 0.006(2) 0.007(2) 0.009(2) N 0.019(2) 0.012(2) 0.016(2) 0.000(2) 0.004(1) 0.003(2) C1 0.016(2) 0.012(2) 0.012(2) -0.001(2) 0.001(2) -0.002(2) C2 0.025(3) 0.011(2) 0.012(2) -0.003(2) 0.001(2) 0.001(2) C3 0.017(2) 0.024(3) 0.018(2) -0.007(2) -0.002(2) 0.007(2) C4 0.020(3) 0.042(4) 0.016(2) -0.013(3) -0.003(2) 0.003(2) C5 0.015(3) 0.042(4) 0.026(3) -0.006(2) -0.003(2) -0.003(3) C6 0.020(3) 0.043(4) 0.016(2) -0.004(3) -0.005(2) 0.000(3) C7 0.019(2) 0.036(3) 0.012(2) -0.005(2) 0.000(2) 0.002(2) C8 0.014(2) 0.033(3) 0.022(3) -0.005(2) 0.001(2) 0.012(2) #================================= # 10. MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 S O2 1.432(4) . . S O1 1.434(5) . . S N 1.595(4) . . S C8 1.838(6) . . F1 C8 1.319(7) . . F2 C8 1.301(8) . . F3 C8 1.325(7) . . N C1 1.481(7) . . C1 C2 1.536(8) . . C1 C1 1.541(10) . 2_556 C2 C7 1.541(7) . . C2 C3 1.513(8) . . C3 C4 1.534(8) . . C4 C5 1.533(9) . . C5 C6 1.517(10) . . C6 C7 1.518(8) . . N H1n 0.83 . . C1 H1 0.95 . . C2 H2 0.95 . . C3 H3b 0.95 . . C3 H3a 0.95 . . C4 H4a 0.95 . . C4 H4b 0.95 . . C5 H5b 0.95 . . C5 H5a 0.95 . . C6 H6b 0.95 . . C6 H6a 0.95 . . C7 H7a 0.95 . . C7 H7b 0.95 . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 O1 S O2 121.6(3) . . . N S O2 110.0(3) . . . C8 S O2 102.7(3) . . . N S O1 110.8(3) . . . C8 S O1 105.0(3) . . . C8 S N 105.0(3) . . . S N C1 124.1(4) . . . C2 C1 N 111.2(4) . . . C1 C1 N 108.8(3) 2_556 . . C1 C1 C2 114.0(5) 2_556 . . C1 C2 C7 112.0(5) . . . C3 C2 C7 109.5(5) . . . C3 C2 C1 112.0(4) . . . C2 C3 C4 112.8(5) . . . C5 C4 C3 112.0(5) . . . C6 C5 C4 110.6(5) . . . C7 C6 C5 111.9(5) . . . C6 C7 C2 112.1(5) . . . F3 C8 F1 107.1(5) . . . F2 C8 F1 107.8(5) . . . S C8 F1 111.3(4) . . . F2 C8 F3 110.5(5) . . . S C8 F3 108.4(4) . . . S C8 F2 111.7(5) . . . C1 N H1n 115.6 . . . S N H1n 110.4 . . . N C1 H1 107.6 . . . C2 C1 H1 107.5 . . . C1 C1 H1 107.5 2_556 . . C7 C2 H2 107.7 . . . C1 C2 H2 107.7 . . . C3 C2 H2 107.7 . . . H3a C3 H3b 109.4 . . . C4 C3 H3b 108.6 . . . C2 C3 H3b 108.6 . . . C4 C3 H3a 108.7 . . . C2 C3 H3a 108.6 . . . H4b C4 H4a 109.5 . . . C3 C4 H4a 108.9 . . . C5 C4 H4a 108.8 . . . C3 C4 H4b 108.8 . . . C5 C4 H4b 108.8 . . . H5a C5 H5b 109.5 . . . C4 C5 H5b 109.1 . . . C6 C5 H5b 109.2 . . . C4 C5 H5a 109.3 . . . C6 C5 H5a 109.2 . . . H6a C6 H6b 109.4 . . . C5 C6 H6b 108.8 . . . C7 C6 H6b 108.9 . . . C5 C6 H6a 108.9 . . . C7 C6 H6a 108.9 . . . H7b C7 H7a 109.5 . . . C2 C7 H7a 108.8 . . . C6 C7 H7a 108.8 . . . C2 C7 H7b 108.8 . . . C6 C7 H7b 108.8 . . . loop_ _publ_manuscript_incl_extra_item '_geom_bond_atom_site_label_D' '_geom_bond_atom_site_label_H' '_geom_contact_atom_site_label_A' '_geom_bond_distance_DH' '_geom_contact_distance_HA' '_geom_contact_distance_DA' '_geom_angle_DHA' '_geom_contact_site_symmetry_A' loop_ _geom_bond_atom_site_label_D _geom_bond_atom_site_label_H _geom_contact_atom_site_label_A _geom_bond_distance_DH _geom_contact_distance_HA _geom_contact_distance_DA _geom_angle_DHA _geom_contact_site_symmetry_A N H1n O1 0.832(5) 2.092(4) 2.924(7) 118.1(3) 3_567 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 N C1 C1 N 61.2(7) . . 2_556 2_556 S N C1 C1 134.5(4) . . . 2_556 C2 C1 C1 C2 171.8(6) . . 2_556 2_556 S C1 C1 S 112.7(5) . . 2_556 2_556 data_wei-4d _database_code_depnum_ccdc_archive 'CCDC 270613' #=================================== # 5. CHEMICAL DATA _chemical_name_systematic ; (S,S) C,C,C-Trifluoro-N-(2-trifluoromethanesulfonylamino-cyclohexyl) -methanesulfonamide ; _chemical_name_common ? _chemical_formula_sum 'C9.80 H12 F6 N2 O4 S2' _chemical_formula_moiety 'C8 H12 F6 N2 O4 S2, C1.80' _chemical_formula_weight 397.43 _chemical_melting_point ? _chemical_compound_source ? #=================================== # 6. CRYSTAL DATA _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'P 32 2 1' _symmetry_space_group_name_Hall 'P 32 2' loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z -y,+x-y,2/3+z -x+y,-x,1/3+z +y,+x,-z +x-y,-y,1/3-z -x,-x+y,2/3-z _cell_length_a 14.3841(2) _cell_length_b 14.3841(2) _cell_length_c 13.9800(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_volume 2504.97(9) _cell_formula_units_Z 6 _cell_measurement_temperature 100 _cell_measurement_reflns_used 5844 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 32.96 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.581 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1209.2 _exptl_absorpt_coefficient_mu 0.398 _exptl_absorpt_correction_type none _exptl_absorpt_process_details none #=================================== # 7. EXPERIMENTAL DATA _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'x-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens SMART CCD diffractometer' _diffrn_measurement_method '\w rotation scans with narrow frames' _diffrn_standards_decay_% 0 _diffrn_reflns_number 24180 _diffrn_reflns_av_R_equivalents 0.081 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.83 _diffrn_reflns_theta_max 32.96 _diffrn_reflns_reduction_process 24180 _reflns_number_total 6270 _diffrn_measured_fraction_theta_max 1.00 _diffrn_measured_fraction_theta_full 1.00 _diffrn_reflns_theta_full 32.96 _reflns_number_gt 5312 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'SMART (Siemens, 1995)' _computing_cell_refinement 'SAINT (Siemens, 1995)' _computing_data_reduction 'SAINT (Siemens, 1995)' _computing_structure_solution ; SIR97 (Altomare et al., 1997 ), KRYSTAL ; _computing_structure_refinement 'modified ORFLS(1962), KRYSTAL' _computing_molecular_graphics ; ORTEP-III (Burnett & Johnson, 1996), KRYSTAL ; _computing_publication_material KRYSTAL _atom_type_scat_source IntTabIV #=================================== # 8. REFINEMENT DATA _refine_special_details ; The structure contains large channels along the unique axis filled by solvent molecules (n-hexane). The solvent is completely disordered, and the carbon atoms C11-C14 are included at the most important peak positions in order to improve the model of the main residue. The peaks form an infinite chain. The hydrogen atoms on nitrogen were located from a difference fourier map but were not refined. They are found to point towards oxygen atoms in neighbouring molecules. ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w= 1/{[\s~cs~(F^2^)+B+(1+A)F^2^]^1/2^- |F|}^2^ where A = 0.03 and B = 0.0 ; _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_abs_structure_details ; The least squares refinement included a factor according to Rogers (1981). 5312 significant reflections were used, including 2288 Bijvoet pairs. ; _refine_ls_abs_structure_Rogers 0.79(9) _refine_ls_number_reflns 5312 _refine_ls_number_parameters 215 _refine_ls_number_restraints 0 _refine_ls_number_constraints 3 _refine_ls_R_factor_gt 0.034 _refine_ls_wR_factor_ref 0.036 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_shift/su_max 0.0043 _refine_ls_shift/su_mean 0.0003 _refine_diff_density_max 0.88(8) _refine_diff_density_min -0.60(8) #========================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS 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_occupancy S1 0.68404(4) 0.41124(3) 0.92124(2) 0.0220(3) Uij 1.0 S2 0.68015(3) 0.13666(4) 0.93408(3) 0.0225(3) Uij 1.0 F1 0.7398(2) 0.6126(1) 0.91148(13) 0.0800(16) Uij 1.0 F2 0.6446(1) 0.5179(1) 0.79345(8) 0.0456(11) Uij 1.0 F3 0.5698(2) 0.5051(1) 0.92854(10) 0.0641(16) Uij 1.0 F4 0.7397(1) -0.0063(1) 0.92304(10) 0.0514(13) Uij 1.0 F5 0.6917(2) 0.0139(1) 1.06451(9) 0.0579(14) Uij 1.0 F6 0.5721(1) -0.0707(1) 0.95551(9) 0.0503(11) Uij 1.0 O1 0.7703(1) 0.4266(1) 0.86050(8) 0.0292(9) Uij 1.0 O2 0.6960(1) 0.4197(1) 1.02280(7) 0.0324(9) Uij 1.0 O3 0.7868(1) 0.2151(1) 0.95780(11) 0.0397(11) Uij 1.0 O4 0.6423(1) 0.1185(1) 0.83778(7) 0.0293(9) Uij 1.0 N1 0.5779(1) 0.3050(1) 0.89403(8) 0.0247(9) Uij 1.0 N2 0.5974(1) 0.1474(1) 1.00138(9) 0.0245(10) Uij 1.0 C1 0.4927(1) 0.2350(1) 0.96202(10) 0.0215(10) Uij 1.0 C2 0.3837(2) 0.2167(2) 0.93030(12) 0.0275(12) Uij 1.0 C3 0.2968(2) 0.1437(2) 1.00150(14) 0.0311(13) Uij 1.0 C4 0.2958(2) 0.0379(2) 1.01540(13) 0.0298(12) Uij 1.0 C5 0.4055(2) 0.0565(1) 1.04462(12) 0.0253(11) Uij 1.0 C6 0.4914(1) 0.1287(1) 0.97259(10) 0.0201(10) Uij 1.0 C7 0.6580(2) 0.5186(2) 0.88710(15) 0.0404(16) Uij 1.0 C8 0.6697(2) 0.0105(2) 0.97142(13) 0.0356(16) Uij 1.0 H1n 0.5702 0.2946 0.8322 0.030 Uiso 1.0 H2n 0.6200 0.1600 1.0533 0.029 Uiso 1.0 H1 0.5090 0.2695 1.0226 0.026 Uiso 1.0 H2a 0.3671 0.1839 0.8690 0.033 Uiso 1.0 H2b 0.3860 0.2838 0.9271 0.033 Uiso 1.0 H3a 0.2287 0.1289 0.9781 0.037 Uiso 1.0 H3b 0.3102 0.1795 1.0614 0.037 Uiso 1.0 H4a 0.2752 -0.0013 0.9571 0.036 Uiso 1.0 H4b 0.2454 -0.0027 1.0639 0.036 Uiso 1.0 H5a 0.4033 -0.0105 1.0478 0.030 Uiso 1.0 H5b 0.4236 0.0899 1.1057 0.030 Uiso 1.0 H6 0.4739 0.0935 0.9123 0.024 Uiso 1.0 C11 0.940(2) 1.000 0.167 0.204(5) Uiso 0.42(1) C12 0.896(2) 0.922(1) 0.106(1) 0.204 Uiso 0.59(2) C13 0.953(2) 0.969(2) 0.036(2) 0.204 Uiso 0.50(1) C14 1.011(3) 0.977(4) 0.154(3) 0.204 Uiso 0.29(1) 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 0.0290(2) 0.0253(2) 0.0080(1) 0.0107(2) 0.0004(1) 0.0003(1) S2 0.0232(2) 0.0287(2) 0.0154(1) 0.0130(2) 0.0010(1) 0.0003(1) F1 0.1038(16) 0.0268(7) 0.0944(13) 0.0213(10) -0.0399(11) -0.0155(8) F2 0.0659(10) 0.0482(8) 0.0300(6) 0.0340(8) 0.0004(6) 0.0137(5) F3 0.0990(14) 0.0833(12) 0.0472(8) 0.0735(12) 0.0116(8) -0.0031(8) F4 0.0679(10) 0.0683(10) 0.0456(7) 0.0548(9) -0.0089(7) -0.0132(7) F5 0.1064(13) 0.0672(10) 0.0243(6) 0.0617(10) -0.0132(7) 0.0014(6) F6 0.0646(10) 0.0285(6) 0.0467(7) 0.0149(7) 0.0061(7) 0.0007(5) O1 0.0310(7) 0.0393(7) 0.0128(4) 0.0142(6) 0.0043(5) 0.0034(5) O2 0.0353(7) 0.0409(8) 0.0078(4) 0.0091(6) -0.0016(4) -0.0018(5) O3 0.0265(7) 0.0458(9) 0.0406(8) 0.0134(7) -0.0015(6) -0.0071(7) O4 0.0361(7) 0.0458(8) 0.0110(4) 0.0243(6) 0.0039(4) 0.0017(4) N1 0.0305(8) 0.0272(7) 0.0073(4) 0.0077(6) 0.0022(5) 0.0005(5) N2 0.0263(8) 0.0379(9) 0.0118(5) 0.0180(7) -0.0024(5) -0.0052(5) C1 0.0273(8) 0.0244(8) 0.0106(5) 0.0113(7) 0.0028(5) 0.0007(5) C2 0.0324(10) 0.0311(9) 0.0238(7) 0.0193(8) -0.0011(7) 0.0005(7) C3 0.0267(10) 0.0334(11) 0.0352(9) 0.0166(8) 0.0040(7) -0.0036(8) C4 0.0262(9) 0.0292(10) 0.0310(9) 0.0116(8) 0.0080(7) 0.0003(7) C5 0.0319(9) 0.0250(8) 0.0182(6) 0.0137(8) 0.0065(6) 0.0033(6) C6 0.0229(8) 0.0266(8) 0.0113(5) 0.0128(7) 0.0009(5) -0.0007(5) C7 0.0608(15) 0.0328(11) 0.0306(9) 0.0257(11) -0.0045(9) -0.0041(8) C8 0.0545(13) 0.0407(12) 0.0221(8) 0.0318(11) -0.0064(8) -0.0026(8) #================================= # 10. MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 S1 O1 1.427(1) . . S1 O2 1.428(1) . . S1 N1 1.574(2) . . S1 C7 1.825(2) . . S2 O3 1.416(2) . . S2 O4 1.426(1) . . S2 N2 1.585(1) . . S2 C8 1.821(2) . . F1 C7 1.319(3) . . F2 C7 1.323(2) . . F3 C7 1.318(3) . . F4 C8 1.331(2) . . F5 C8 1.334(2) . . F6 C8 1.321(3) . . N1 C1 1.479(2) . . N2 C6 1.465(2) . . C1 C2 1.520(2) . . C1 C6 1.527(2) . . C2 C3 1.531(3) . . C3 C4 1.528(3) . . C4 C5 1.519(3) . . C5 C6 1.528(2) . . N1 H1n 0.88 . . N2 H2n 0.78 . . C1 H1 0.95 . . C2 H2a 0.95 . . C2 H2b 0.95 . . C3 H3b 0.95 . . C3 H3a 0.95 . . C4 H4a 0.95 . . C4 H4b 0.95 . . C5 H5a 0.95 . . C5 H5b 0.95 . . C6 H6 0.95 . . C11 C14 1.229(30) . . C11 C14 1.229(30) . 5_675 C11 C12 1.296(18) . . C11 C12 1.296(18) . 5_675 C12 C13 1.233(19) . . C12 C14 1.581(38) . . C13 C13 1.074(41) . 4_555 C13 C14 1.831(47) . . C14 C14 0.68(8) . 5_675 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 O2 S1 O1 121.32(8) . . . N1 S1 O1 110.63(8) . . . C7 S1 O1 104.1(1) . . . N1 S1 O2 109.90(7) . . . C7 S1 O2 104.78(9) . . . C7 S1 N1 104.4(1) . . . O4 S2 O3 121.95(9) . . . N2 S2 O3 110.54(8) . . . C8 S2 O3 104.1(1) . . . N2 S2 O4 109.97(7) . . . C8 S2 O4 104.74(9) . . . C8 S2 N2 103.64(9) . . . S1 N1 C1 125.3(1) . . . S2 N2 C6 125.6(1) . . . C2 C1 N1 111.3(1) . . . C6 C1 N1 109.6(1) . . . C6 C1 C2 111.1(1) . . . C3 C2 C1 110.3(1) . . . C2 C3 C4 111.4(2) . . . C3 C4 C5 111.5(2) . . . C6 C5 C4 111.0(1) . . . C1 C6 N2 110.6(1) . . . C5 C6 N2 110.9(1) . . . C5 C6 C1 110.2(1) . . . F1 C7 F3 109.6(2) . . . F2 C7 F3 108.0(2) . . . S1 C7 F3 110.5(2) . . . F2 C7 F1 108.4(2) . . . S1 C7 F1 110.2(2) . . . S1 C7 F2 110.1(1) . . . F4 C8 F6 108.7(2) . . . F5 C8 F6 108.9(2) . . . S2 C8 F6 110.7(1) . . . F5 C8 F4 108.4(2) . . . S2 C8 F4 110.0(2) . . . S2 C8 F5 110.0(1) . . . C1 N1 H1n 121.9 . . . S1 N1 H1n 112.5 . . . C6 N2 H2n 125.0 . . . S2 N2 H2n 109.2 . . . N1 C1 H1 108.3 . . . C2 C1 H1 108.3 . . . C6 C1 H1 108.2 . . . H2b C2 H2a 109.5 . . . C1 C2 H2a 109.3 . . . C3 C2 H2a 109.3 . . . C1 C2 H2b 109.2 . . . C3 C2 H2b 109.2 . . . H3a C3 H3b 109.4 . . . C4 C3 H3b 109.0 . . . C2 C3 H3b 109.0 . . . C4 C3 H3a 109.0 . . . C2 C3 H3a 109.0 . . . H4b C4 H4a 109.4 . . . C5 C4 H4a 108.9 . . . C3 C4 H4a 109.0 . . . C5 C4 H4b 108.9 . . . C3 C4 H4b 109.0 . . . H5b C5 H5a 109.5 . . . C4 C5 H5a 109.2 . . . C6 C5 H5a 109.0 . . . C4 C5 H5b 109.2 . . . C6 C5 H5b 109.0 . . . N2 C6 H6 108.4 . . . C1 C6 H6 108.4 . . . C5 C6 H6 108.3 . . . C12 C11 C14 109.0(25) 5_675 . . C12 C11 C14 77.5(21) . . . C12 C11 C12 173.6(27) 5_675 . . C11 C12 C13 98.4(17) . . . C14 C12 C13 80.2(24) . . . C12 C13 C13 140.6(17) . . 4_555 C14 C13 C13 135.4(31) . . 4_555 C14 C13 C12 58.3(18) . . . C11 C14 C14 74.0(19) . . 5_675 C12 C14 C14 126.3(23) . . 5_675 C13 C14 C14 121(8) . . 5_675 C13 C14 C11 74.6(20) . . . loop_ _publ_manuscript_incl_extra_item '_geom_bond_atom_site_label_D' '_geom_bond_atom_site_label_H' '_geom_contact_atom_site_label_A' '_geom_bond_distance_DH' '_geom_contact_distance_HA' '_geom_contact_distance_DA' '_geom_angle_DHA' '_geom_contact_site_symmetry_A' loop_ _geom_bond_atom_site_label_D _geom_bond_atom_site_label_H _geom_contact_atom_site_label_A _geom_bond_distance_DH _geom_contact_distance_HA _geom_contact_distance_DA _geom_angle_DHA _geom_contact_site_symmetry_A N1 H1n O2 0.88 2.03 2.892(2) 170 2_654 N2 H2n O1 0.78 2.15 2.890(2) 160 3_665 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 N1 C1 C6 N2 55.6(2) . . . . S1 N1 C1 C6 -111.1(1) . . . . C1 C6 N2 S2 -105.4(1) . . . . #Dihedral angle: # S1 N1 C1 - C1' N1' S2' 51.8(1) . . . . # Intramolecular distances: # S1 S2 3.926(1) . . # N1 N2 2.844(2) . . # N1 H2n 3.307(1) . . # N2 H1n 3.324(1) . . # H1n H2n 3.899(0) . . # H1n H5b 2.745(0) . . # H2n H1 2.780(0) . . #============================================================================== data_wei-4a _database_code_depnum_ccdc_archive 'CCDC 272816' #=================================== # 5. CHEMICAL DATA _chemical_name_systematic ; (R,R) N-(1,2-Diphenyl-2-trifluoromethanesulfonylamino-ethyl)- C,C,C-trifluoro-methanesulfonamide ; _chemical_formula_sum 'C16 H14 F6 N2 O4 S2' _chemical_formula_moiety 'C16 H14 F6 N2 O4 S2' _chemical_formula_weight 476.42 _chemical_melting_point ? _chemical_compound_source ? #=================================== # 6. CRYSTAL DATA _symmetry_cell_setting hexagonal _symmetry_space_group_name_H-M 'P 65 2 2' _symmetry_space_group_name_Hall 'P 65 2 (0 0 1)' loop_ _symmetry_equiv_pos_as_xyz +x,+y,+z -y,+x-y,2/3+z -x+y,-x,1/3+z -x,-y,1/2+z +y,-x+y,1/6+z +x-y,+x,5/6+z +y,+x,2/3-z +x-y,-y,-z -x,-x+y,1/3-z -y,-x,1/6-z -x+y,+y,1/2-z +x,+x-y,5/6-z _cell_length_a 11.6353(10) _cell_length_b 11.6353(10) _cell_length_c 52.806(9) _cell_angle_alpha 90.000 _cell_angle_beta 90.000 _cell_angle_gamma 120.000 _cell_volume 6191.1(13) _cell_formula_units_Z 12 _cell_measurement_temperature 100 _cell_measurement_reflns_used 7007 _cell_measurement_theta_min 3.07 _cell_measurement_theta_max 28.14 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.533 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2904 _exptl_absorpt_coefficient_mu 0.336 _exptl_absorpt_correction_type none _exptl_absorpt_process_details none #=================================== # 7. EXPERIMENTAL DATA _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'x-ray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens SMART CCD diffractometer' _diffrn_measurement_method 'scans with narrow frames ' _diffrn_standards_decay_% 0 _diffrn_reflns_number 62518 _diffrn_reflns_av_R_equivalents 0.107 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -66 _diffrn_reflns_limit_l_max 55 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 28.14 _diffrn_reflns_reduction_process 62518 _reflns_number_total 5027 _diffrn_measured_fraction_theta_max 0.97 _diffrn_measured_fraction_theta_full 0.989 _diffrn_reflns_theta_full 20.82 _reflns_number_gt 4303 _reflns_threshold_expression I>3\s(I) _computing_data_collection 'SMART (Siemens, 1995)' _computing_cell_refinement 'SAINT (Siemens, 1995)' _computing_data_reduction 'SAINT (Siemens, 1995)' _computing_structure_solution ; SIR97 (Altomare et al., 1997 ), KRYSTAL ; _computing_structure_refinement 'modified ORFLS(1962), KRYSTAL' _computing_molecular_graphics ; ORTEP-III (Burnett & Johnson, 1996), KRYSTAL ; _computing_publication_material KRYSTAL _atom_type_scat_source IntTabIV #=================================== # 8. REFINEMENT DATA _refine_special_details ; The crystals available were small and poorly diffracting. Both one triflate- group and one phenyl show large thermal motion. The largest peaks and holes in the final difference map are found in these regions. The hydrogen atoms on nitrogen were located from a difference fourier map and their coordinates refined. ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w= 1/{[\s~cs~(F^2^)+B+(1+A)F^2^]^1/2^- |F|}^2^ where A = 0.05 and B = 0.25 ; _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method ; Type 1 Lorentzian isotropic (Becker and Coppens, 1974) ; _refine_ls_extinction_coef 1396(144) _refine_ls_abs_structure_details ; The least squares refinement included a factor according to Rogers (1981). 4303 significant reflections were used, including 1598 Bijvoet pairs. ; _refine_ls_abs_structure_Rogers 1.02(24) _refine_ls_number_reflns 4303 _refine_ls_number_parameters 279 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_gt 0.064 _refine_ls_wR_factor_ref 0.081 _refine_ls_goodness_of_fit_ref 1.70 _refine_ls_shift/su_max 0.0006 _refine_ls_shift/su_mean 0.00005 _refine_diff_density_max 0.8(1) _refine_diff_density_min -1.1(1) #========================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS 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 S1 0.77079(15) 0.59057(12) 0.34188(2) 0.0511(9) Uij S2 1.03508(9) 0.72498(8) 0.25645(2) 0.0195(5) Uij F1 0.9135(4) 0.5298(3) 0.37058(6) 0.069(3) Uij F2 0.8301(5) 0.4046(3) 0.33810(8) 0.099(4) Uij F3 0.9970(4) 0.6026(3) 0.33370(7) 0.074(3) Uij F4 1.2513(3) 0.7674(4) 0.27836(7) 0.069(3) Uij F5 1.0915(3) 0.5691(3) 0.28185(6) 0.048(2) Uij F6 1.1948(4) 0.6353(4) 0.24651(6) 0.070(4) Uij O1 0.6628(4) 0.5134(4) 0.35866(7) 0.071(3) Uij O2 0.7526(4) 0.5866(3) 0.31516(6) 0.055(3) Uij O3 0.9866(3) 0.7471(3) 0.27948(5) 0.028(2) Uij O4 1.1066(3) 0.8296(2) 0.23891(5) 0.029(2) Uij N1 0.8479(4) 0.7381(4) 0.35141(7) 0.037(3) Uij N2 0.9209(3) 0.6036(3) 0.24172(6) 0.023(2) Uij C1 0.9312(4) 0.8567(4) 0.33600(7) 0.026(3) Uij C2 1.0625(4) 0.9422(4) 0.34920(8) 0.031(3) Uij C3 1.0694(5) 1.0147(5) 0.37072(9) 0.042(4) Uij C4 1.1896(6) 1.0970(6) 0.38175(11) 0.053(4) Uij C5 1.3062(6) 1.1111(6) 0.37225(12) 0.056(4) Uij C6 1.2983(5) 1.0369(7) 0.35134(12) 0.057(5) Uij C7 1.1788(5) 0.9540(5) 0.33988(9) 0.041(4) Uij C8 0.8844(8) 0.5290(5) 0.34633(11) 0.070(6) Uij C11 0.8075(3) 0.4866(3) 0.25355(7) 0.022(2) Uij C12 0.8035(4) 0.3598(4) 0.24542(8) 0.028(3) Uij C13 0.8056(5) 0.3309(4) 0.22031(9) 0.037(3) Uij C14 0.7923(5) 0.2105(5) 0.21310(11) 0.048(4) Uij C15 0.7741(5) 0.1170(5) 0.23129(13) 0.053(4) Uij C16 0.7724(5) 0.1456(5) 0.25635(12) 0.050(4) Uij C17 0.7855(4) 0.2653(4) 0.26356(10) 0.040(3) Uij C18 1.1516(4) 0.6714(5) 0.26605(9) 0.037(3) Uij H1n 0.852(6) 0.744(6) 0.3645(9) 0.043 Uiso H2n 0.931(5) 0.608(5) 0.2284(9) 0.027 Uiso H1 0.9466 0.8297 0.31996 0.031 Uiso H3 0.9908 1.0078 0.37765 0.051 Uiso H4 1.1927 1.1464 0.39624 0.063 Uiso H5 1.3892 1.1698 0.37984 0.067 Uiso H6 1.3771 1.0422 0.34480 0.069 Uiso H7 1.1759 0.9043 0.32533 0.049 Uiso H11 0.8161 0.4947 0.27142 0.027 Uiso H13 0.8163 0.3935 0.20773 0.043 Uiso H14 0.7949 0.1919 0.19559 0.057 Uiso H15 0.7632 0.0340 0.22625 0.064 Uiso H16 0.7622 0.0821 0.26876 0.060 Uiso H17 0.7819 0.2836 0.28094 0.048 Uiso 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 0.0625(9) 0.0293(6) 0.0286(6) -0.0016(6) 0.0085(5) 0.0025(5) S2 0.0206(4) 0.0166(4) 0.0171(4) 0.0062(3) -0.0001(3) 0.0006(3) F1 0.107(3) 0.050(2) 0.051(2) 0.039(2) 0.006(2) 0.012(2) F2 0.175(5) 0.038(2) 0.078(3) 0.047(3) 0.015(3) 0.001(2) F3 0.109(3) 0.055(2) 0.074(2) 0.052(2) 0.031(2) 0.016(2) F4 0.038(2) 0.063(2) 0.084(3) 0.009(2) -0.032(2) 0.009(2) F5 0.056(2) 0.042(2) 0.053(2) 0.031(1) -0.003(1) 0.016(1) F6 0.074(2) 0.127(3) 0.055(2) 0.086(2) 0.012(2) 0.014(2) O1 0.069(3) 0.051(2) 0.042(2) -0.009(2) 0.009(2) 0.009(2) O2 0.073(3) 0.030(2) 0.029(2) 0.001(2) 0.000(2) -0.004(1) O3 0.031(1) 0.027(1) 0.020(1) 0.010(1) 0.001(1) -0.001(1) O4 0.031(1) 0.020(1) 0.020(1) 0.002(1) 0.002(1) 0.006(1) N1 0.042(2) 0.035(2) 0.018(2) 0.008(2) 0.012(2) -0.001(2) N2 0.025(2) 0.014(1) 0.020(2) 0.004(1) -0.002(1) 0.001(1) C1 0.036(2) 0.028(2) 0.013(2) 0.015(2) 0.009(1) 0.001(1) C2 0.040(2) 0.027(2) 0.027(2) 0.017(2) 0.003(2) 0.002(2) C3 0.045(3) 0.056(3) 0.038(3) 0.035(2) -0.009(2) -0.009(2) C4 0.057(3) 0.050(3) 0.066(4) 0.038(3) -0.029(3) -0.018(3) C5 0.045(3) 0.056(3) 0.075(4) 0.029(3) -0.020(3) 0.002(3) C6 0.033(3) 0.074(4) 0.072(4) 0.033(3) 0.010(3) 0.022(3) C7 0.048(3) 0.042(3) 0.039(2) 0.027(2) 0.012(2) 0.012(2) C8 0.118(6) 0.031(3) 0.047(3) 0.027(3) 0.017(4) 0.009(2) C11 0.020(2) 0.011(1) 0.027(2) 0.001(1) -0.004(1) 0.004(1) C12 0.027(2) 0.016(2) 0.039(2) 0.009(2) -0.008(2) -0.002(2) C13 0.042(3) 0.025(2) 0.045(3) 0.019(2) -0.006(2) -0.001(2) C14 0.053(3) 0.031(2) 0.064(3) 0.024(2) -0.005(3) -0.013(2) C15 0.049(3) 0.022(2) 0.097(5) 0.025(2) -0.004(3) -0.006(2) C16 0.040(3) 0.030(2) 0.086(4) 0.022(2) 0.008(3) 0.021(3) C17 0.036(2) 0.028(2) 0.056(3) 0.016(2) -0.004(2) 0.012(2) C18 0.025(2) 0.042(3) 0.043(3) 0.017(2) -0.002(2) 0.009(2) #================================= # 10. MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 S1 O2 1.424(4) . . S1 O1 1.429(4) . . S1 N1 1.570(4) . . S1 C8 1.807(8) . . S2 O3 1.417(3) . . S2 O4 1.421(3) . . S2 N2 1.577(3) . . S2 C18 1.824(4) . . F1 C8 1.323(7) . . F2 C8 1.330(7) . . F3 C8 1.331(8) . . F4 C18 1.311(5) . . F5 C18 1.331(5) . . F6 C18 1.306(6) . . N1 C1 1.472(5) . . N2 C11 1.480(4) . . C1 C2 1.513(6) . . C1 C1 1.529(9) . 7_555 C2 C7 1.381(7) . . C2 C3 1.393(6) . . C3 C4 1.369(7) . . C4 C5 1.378(8) . . C5 C6 1.376(9) . . C6 C7 1.375(8) . . C11 C12 1.514(5) . . C11 C11 1.542(7) . 11_655 C12 C13 1.372(7) . . C12 C17 1.392(6) . . C13 C14 1.383(6) . . C14 C15 1.386(8) . . C15 C16 1.367(8) . . C16 C17 1.377(7) . . N1 H1n 0.69(5) . . N2 H2n 0.709(45) . . C1 H1 0.95 . . C3 H3 0.95 . . C4 H4 0.95 . . C5 H5 0.95 . . C6 H6 0.95 . . C7 H7 0.95 . . C11 H11 0.95 . . C13 H13 0.95 . . C14 H14 0.95 . . C15 H15 0.95 . . C16 H16 0.95 . . C17 H17 0.95 . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 O1 S1 O2 121.6(3) . . . N1 S1 O2 110.3(2) . . . C8 S1 O2 104.1(3) . . . N1 S1 O1 109.3(2) . . . C8 S1 O1 105.0(3) . . . C8 S1 N1 105.1(3) . . . O4 S2 O3 121.3(2) . . . N2 S2 O3 110.6(2) . . . C18 S2 O3 104.7(2) . . . N2 S2 O4 108.4(2) . . . C18 S2 O4 104.9(2) . . . C18 S2 N2 105.6(2) . . . S1 N1 C1 126.6(3) . . . S2 N2 C11 125.4(3) . . . C2 C1 N1 109.7(3) . . . C1 C1 N1 109.8(3) 7_555 . . C1 C1 C2 112.6(3) 7_555 . . C3 C2 C7 118.3(5) . . . C1 C2 C7 121.2(4) . . . C1 C2 C3 120.5(4) . . . C2 C3 C4 120.0(5) . . . C5 C4 C3 122.0(5) . . . C4 C5 C6 117.7(5) . . . C5 C6 C7 121.4(5) . . . C2 C7 C6 120.7(5) . . . F2 C8 F1 107.7(5) . . . F3 C8 F1 108.3(6) . . . S1 C8 F1 111.0(5) . . . F3 C8 F2 108.4(5) . . . S1 C8 F2 110.2(6) . . . S1 C8 F3 111.1(4) . . . C12 C11 N2 110.9(3) . . . C11 C11 N2 108.4(3) 11_655 . . C11 C11 C12 111.9(2) 11_655 . . C17 C12 C13 119.0(4) . . . C11 C12 C13 121.2(4) . . . C11 C12 C17 119.5(4) . . . C14 C13 C12 120.5(4) . . . C15 C14 C13 120.0(5) . . . C14 C15 C16 119.6(4) . . . C17 C16 C15 120.4(5) . . . C12 C17 C16 120.3(5) . . . F4 C18 F6 110.3(4) . . . F5 C18 F6 108.8(4) . . . S2 C18 F6 111.2(3) . . . F5 C18 F4 107.3(4) . . . S2 C18 F4 109.8(3) . . . S2 C18 F5 109.4(3) . . . C1 N1 H1n 119(5) . . . S1 N1 H1n 114(5) . . . C11 N2 H2n 122(4) . . . S2 N2 H2n 113(4) . . . N1 C1 H1 109.1 . . . C2 C1 H1 109.5 . . . C1 C1 H1 106.1 7_555 . . C4 C3 H3 119.9 . . . C2 C3 H3 120.1 . . . C3 C4 H4 119.0 . . . C5 C4 H4 119.0 . . . C6 C5 H5 121.0 . . . C4 C5 H5 121.3 . . . C7 C6 H6 119.2 . . . C5 C6 H6 119.4 . . . C6 C7 H7 119.9 . . . C2 C7 H7 119.5 . . . N2 C11 H11 109.1 . . . C12 C11 H11 109.3 . . . C11 C11 H11 107.2 11_655 . . C12 C13 H13 120.1 . . . C14 C13 H13 119.4 . . . C13 C14 H14 119.8 . . . C15 C14 H14 120.2 . . . C16 C15 H15 120.7 . . . C14 C15 H15 119.7 . . . C15 C16 H16 119.3 . . . C17 C16 H16 120.2 . . . C16 C17 H17 120.0 . . . C12 C17 H17 119.7 . . . loop_ _publ_manuscript_incl_extra_item '_geom_bond_atom_site_label_D' '_geom_bond_atom_site_label_H' '_geom_contact_atom_site_label_A' '_geom_bond_distance_DH' '_geom_contact_distance_HA' '_geom_contact_distance_DA' '_geom_angle_DHA' '_geom_contact_site_symmetry_A' loop_ _geom_bond_atom_site_label_D _geom_bond_atom_site_label_H _geom_contact_atom_site_label_A _geom_bond_distance_DH _geom_contact_distance_HA _geom_contact_distance_DA _geom_angle_DHA _geom_contact_site_symmetry_A N1 H1n O4 0.69(5) 2.18(5) 2.867(4) 169(6) 5_565 N2 H2n O2 0.71(5) 2.52(5) 3.144(5) 148(5) 11_655 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 N1 C1 C1 N1 -64.1(6) . . 7_555 7_555 N2 C11 C11 N2 -65.7(5) . . 11_655 11_655 S1 N1 C1 C1 104.1(5) . . . 7_555 S2 N2 C11 C11 114.4(4) . . . 11_655