# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_vbb86 #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H21 N O3 S' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C18 H21 N O3 S' _chemical_formula_iupac ? _chemical_formula_weight 331.43 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 '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' N N 0.0061 0.0033 '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' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 21' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,1/2+y,-z _cell_length_a 7.4739(8) _cell_length_b 9.911(1) _cell_length_c 11.8150(12) _cell_angle_alpha 90 _cell_angle_beta 102.072(2) _cell_angle_gamma 90 _cell_volume 855.83(15) _cell_formula_units_Z 2 _cell_measurement_temperature 295(1) _cell_measurement_reflns_used 6034 _cell_measurement_theta_min 1.8 _cell_measurement_theta_max 25.0 _cell_special_details ; ; _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.29 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 352.0 _exptl_absorpt_coefficient_mu 0.203 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9416 _exptl_absorpt_correction_T_max 0.9605 _exptl_absorpt_process_details 'Apex2 (Bruker)' _exptl_crystal_density_meas_temp ? #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 295(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_measurement_device_type 'Bruker Smart apex2 CCD area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_number 6034 _diffrn_reflns_av_R_equivalents 0.0243 _diffrn_reflns_av_sigmaI/netI 0.0407 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 2950 # number of observed reflections (> n sig(I)) _reflns_number_gt 2631 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker kappa Apex2' _computing_cell_refinement Apex2 _computing_data_reduction SAINT32 _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'WinGX (Farrugia, 1999)' #=============================================================================== # 8. REFINEMENT DATA _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^)+(0.0388P)^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_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _chemical_absolute_configuration syn _refine_ls_abs_structure_Flack 0.08(8) _refine_ls_number_reflns 2950 _refine_ls_number_parameters 210 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0460 _refine_ls_R_factor_gt 0.0381 _refine_ls_wR_factor_ref 0.0979 _refine_ls_wR_factor_gt 0.0928 _refine_ls_goodness_of_fit_ref 1.156 _refine_ls_restrained_S_all 1.155 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.147 _refine_diff_density_min -0.168 _refine_diff_density_rms 0.035 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 S1 S 0.40885(9) 0.47346(6) 0.89113(6) 0.05218(19) Uani 1 1 d . . . O1 O 0.3860(3) 0.1282(2) 0.75565(18) 0.0679(6) Uani 1 1 d . . . O2 O 0.6000(2) 0.4835(2) 0.94155(16) 0.0652(5) Uani 1 1 d . . . O3 O 0.3146(3) 0.5870(2) 0.83312(19) 0.0704(6) Uani 1 1 d . . . N1 N 0.3894(3) 0.3538(2) 0.79594(18) 0.0469(5) Uani 1 1 d . . . C1 C 0.4951(4) 0.2262(3) 0.8248(2) 0.0552(7) Uani 1 1 d . . . H1 H 0.5047 0.2046 0.9068 0.066 Uiso 1 1 calc R . . C2 C 0.2000(5) 0.1695(4) 0.7464(3) 0.0758(9) Uani 1 1 d . . . H2A H 0.1584 0.1499 0.8171 0.091 Uiso 1 1 calc R . . H2B H 0.1200 0.1247 0.6822 0.091 Uiso 1 1 calc R . . C3 C 0.2050(4) 0.3206(3) 0.7258(2) 0.0557(7) Uani 1 1 d . . . H3 H 0.1097 0.3661 0.7574 0.067 Uiso 1 1 calc R . . C4 C 0.2954(4) 0.4235(3) 1.0001(2) 0.0503(7) Uani 1 1 d . . . C5 C 0.3893(4) 0.3505(3) 1.0939(2) 0.0574(7) Uani 1 1 d . . . H5 H 0.5120 0.3292 1.0994 0.069 Uiso 1 1 calc R . . C6 C 0.2996(4) 0.3095(3) 1.1794(3) 0.0648(8) Uani 1 1 d . . . H6 H 0.3638 0.2615 1.2427 0.078 Uiso 1 1 calc R . . C7 C 0.1170(4) 0.3383(3) 1.1726(3) 0.0628(8) Uani 1 1 d . . . C8 C 0.0248(4) 0.4099(3) 1.0779(3) 0.0657(9) Uani 1 1 d . . . H8 H -0.0984 0.4298 1.0719 0.079 Uiso 1 1 calc R . . C9 C 0.1118(4) 0.4526(3) 0.9922(2) 0.0596(8) Uani 1 1 d . . . H9 H 0.0473 0.5008 0.9291 0.072 Uiso 1 1 calc R . . C10 C 0.0229(5) 0.2966(4) 1.2681(3) 0.0903(12) Uani 1 1 d . . . H10A H 0.0487 0.2034 1.2868 0.135 Uiso 1 1 calc R . . H10B H -0.1068 0.3088 1.2430 0.135 Uiso 1 1 calc R . . H10C H 0.0668 0.3511 1.3353 0.135 Uiso 1 1 calc R . . C11 C 0.6834(4) 0.2276(3) 0.7974(2) 0.0597(7) Uani 1 1 d . . . H11A H 0.7626 0.2840 0.8538 0.072 Uiso 1 1 calc R . . H11B H 0.7326 0.1367 0.8055 0.072 Uiso 1 1 calc R . . C12 C 0.6879(3) 0.2784(3) 0.6780(2) 0.0509(7) Uani 1 1 d . . . C13 C 0.7036(4) 0.4152(3) 0.6574(3) 0.0604(8) Uani 1 1 d . . . H13 H 0.7200 0.4757 0.7189 0.073 Uiso 1 1 calc R . . C14 C 0.6949(4) 0.4625(4) 0.5462(3) 0.0701(8) Uani 1 1 d . . . H14 H 0.7040 0.5546 0.5332 0.084 Uiso 1 1 calc R . . C15 C 0.6731(4) 0.3739(4) 0.4550(3) 0.0716(9) Uani 1 1 d . . . H15 H 0.6661 0.4059 0.3803 0.086 Uiso 1 1 calc R . . C16 C 0.6617(4) 0.2390(4) 0.4743(3) 0.0696(9) Uani 1 1 d . . . H16 H 0.6488 0.1788 0.4127 0.084 Uiso 1 1 calc R . . C17 C 0.6694(4) 0.1913(3) 0.5850(3) 0.0591(7) Uani 1 1 d . . . H17 H 0.6619 0.0989 0.5972 0.071 Uiso 1 1 calc R . . C18 C 0.1906(4) 0.3590(4) 0.6002(2) 0.0736(9) Uani 1 1 d . . . H18A H 0.2046 0.4549 0.5943 0.110 Uiso 1 1 calc R . . H18B H 0.0730 0.3325 0.5560 0.110 Uiso 1 1 calc R . . H18C H 0.2849 0.3140 0.5705 0.110 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 S1 0.0513(4) 0.0428(3) 0.0589(4) -0.0027(3) 0.0033(3) 0.0014(3) O1 0.0781(15) 0.0478(12) 0.0804(14) -0.0069(11) 0.0227(11) -0.0062(10) O2 0.0501(10) 0.0669(13) 0.0743(12) -0.0091(12) 0.0029(9) -0.0082(11) O3 0.0786(15) 0.0442(12) 0.0836(14) 0.0076(11) 0.0056(12) 0.0098(10) N1 0.0440(12) 0.0474(13) 0.0461(12) 0.0008(10) 0.0023(9) 0.0025(10) C1 0.0686(18) 0.0479(16) 0.0486(14) 0.0053(13) 0.0112(13) 0.0058(14) C2 0.074(2) 0.069(2) 0.091(2) -0.0124(19) 0.0311(18) -0.0231(19) C3 0.0460(16) 0.0592(18) 0.0612(16) -0.0061(14) 0.0094(13) -0.0056(13) C4 0.0482(15) 0.0487(15) 0.0496(14) -0.0128(12) 0.0002(12) 0.0053(12) C5 0.0508(16) 0.0585(18) 0.0603(16) -0.0075(14) 0.0058(13) 0.0051(14) C6 0.070(2) 0.061(2) 0.0592(17) -0.0022(15) 0.0047(15) 0.0059(16) C7 0.066(2) 0.066(2) 0.0561(17) -0.0205(16) 0.0113(14) -0.0123(16) C8 0.0480(16) 0.085(2) 0.0632(17) -0.0280(17) 0.0085(14) 0.0004(16) C9 0.0527(15) 0.068(2) 0.0523(14) -0.0152(15) -0.0019(12) 0.0140(15) C10 0.096(3) 0.103(3) 0.080(2) -0.018(2) 0.036(2) -0.022(2) C11 0.0562(17) 0.0603(19) 0.0601(16) 0.0029(15) 0.0063(13) 0.0150(15) C12 0.0372(14) 0.0532(18) 0.0615(16) 0.0065(14) 0.0089(12) 0.0089(12) C13 0.0485(16) 0.0541(18) 0.0790(19) 0.0015(15) 0.0138(15) 0.0035(14) C14 0.0623(18) 0.0590(19) 0.093(2) 0.022(2) 0.0252(16) 0.0081(18) C15 0.062(2) 0.088(3) 0.070(2) 0.021(2) 0.0240(16) 0.0088(18) C16 0.070(2) 0.077(2) 0.0625(18) -0.0012(17) 0.0170(15) 0.0047(18) C17 0.0586(17) 0.0492(17) 0.0684(19) -0.0012(15) 0.0105(14) 0.0028(14) C18 0.0577(18) 0.100(3) 0.0549(16) -0.0029(17) -0.0060(14) -0.0057(18) _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 S1 O3 1.425(2) . ? S1 O2 1.4315(18) . ? S1 N1 1.620(2) . ? S1 C4 1.755(3) . ? O1 C1 1.413(3) . ? O1 C2 1.431(4) . ? N1 C3 1.488(3) . ? N1 C1 1.493(3) . ? C1 C11 1.508(4) . ? C1 H1 0.9800 . ? C2 C3 1.519(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C18 1.515(4) . ? C3 H3 0.9800 . ? C4 C5 1.385(4) . ? C4 C9 1.386(4) . ? C5 C6 1.385(4) . ? C5 H5 0.9300 . ? C6 C7 1.381(4) . ? C6 H6 0.9300 . ? C7 C8 1.381(4) . ? C7 C10 1.506(4) . ? C8 C9 1.380(4) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.504(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C17 1.382(4) . ? C12 C13 1.387(4) . ? C13 C14 1.384(4) . ? C13 H13 0.9300 . ? C14 C15 1.373(5) . ? C14 H14 0.9300 . ? C15 C16 1.362(5) . ? C15 H15 0.9300 . ? C16 C17 1.381(4) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? 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 O3 S1 O2 119.68(14) . . ? O3 S1 N1 106.29(12) . . ? O2 S1 N1 106.08(12) . . ? O3 S1 C4 108.04(13) . . ? O2 S1 C4 107.90(12) . . ? N1 S1 C4 108.43(12) . . ? C1 O1 C2 106.4(2) . . ? C3 N1 C1 108.9(2) . . ? C3 N1 S1 119.12(18) . . ? C1 N1 S1 119.71(16) . . ? O1 C1 N1 103.7(2) . . ? O1 C1 C11 109.5(2) . . ? N1 C1 C11 114.6(2) . . ? O1 C1 H1 109.6 . . ? N1 C1 H1 109.6 . . ? C11 C1 H1 109.6 . . ? O1 C2 C3 103.8(2) . . ? O1 C2 H2A 111.0 . . ? C3 C2 H2A 111.0 . . ? O1 C2 H2B 111.0 . . ? C3 C2 H2B 111.0 . . ? H2A C2 H2B 109.0 . . ? N1 C3 C18 111.0(2) . . ? N1 C3 C2 100.4(2) . . ? C18 C3 C2 113.9(3) . . ? N1 C3 H3 110.4 . . ? C18 C3 H3 110.4 . . ? C2 C3 H3 110.4 . . ? C5 C4 C9 119.5(3) . . ? C5 C4 S1 119.5(2) . . ? C9 C4 S1 121.0(2) . . ? C4 C5 C6 119.7(3) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C7 C6 C5 121.4(3) . . ? C7 C6 H6 119.3 . . ? C5 C6 H6 119.3 . . ? C6 C7 C8 118.2(3) . . ? C6 C7 C10 120.7(3) . . ? C8 C7 C10 121.0(3) . . ? C9 C8 C7 121.4(3) . . ? C9 C8 H8 119.3 . . ? C7 C8 H8 119.3 . . ? C8 C9 C4 119.9(3) . . ? C8 C9 H9 120.1 . . ? C4 C9 H9 120.1 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C1 114.1(2) . . ? C12 C11 H11A 108.7 . . ? C1 C11 H11A 108.7 . . ? C12 C11 H11B 108.7 . . ? C1 C11 H11B 108.7 . . ? H11A C11 H11B 107.6 . . ? C17 C12 C13 118.0(3) . . ? C17 C12 C11 121.2(3) . . ? C13 C12 C11 120.7(3) . . ? C14 C13 C12 120.6(3) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C15 C14 C13 120.2(3) . . ? C15 C14 H14 119.9 . . ? C13 C14 H14 119.9 . . ? C16 C15 C14 119.9(3) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 C17 120.2(3) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C16 C17 C12 121.1(3) . . ? C16 C17 H17 119.4 . . ? C12 C17 H17 119.4 . . ? C3 C18 H18A 109.5 . . ? C3 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C3 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 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 O3 S1 N1 C3 -50.2(2) . . . . ? O2 S1 N1 C3 -178.62(19) . . . . ? C4 S1 N1 C3 65.7(2) . . . . ? O3 S1 N1 C1 171.65(19) . . . . ? O2 S1 N1 C1 43.3(2) . . . . ? C4 S1 N1 C1 -72.4(2) . . . . ? C2 O1 C1 N1 -32.6(3) . . . . ? C2 O1 C1 C11 -155.3(2) . . . . ? C3 N1 C1 O1 9.9(3) . . . . ? S1 N1 C1 O1 151.89(17) . . . . ? C3 N1 C1 C11 129.3(2) . . . . ? S1 N1 C1 C11 -88.8(3) . . . . ? C1 O1 C2 C3 42.9(3) . . . . ? C1 N1 C3 C18 -106.2(3) . . . . ? S1 N1 C3 C18 111.6(3) . . . . ? C1 N1 C3 C2 14.6(3) . . . . ? S1 N1 C3 C2 -127.6(2) . . . . ? O1 C2 C3 N1 -33.9(3) . . . . ? O1 C2 C3 C18 84.8(3) . . . . ? O3 S1 C4 C5 -157.0(2) . . . . ? O2 S1 C4 C5 -26.3(3) . . . . ? N1 S1 C4 C5 88.2(2) . . . . ? O3 S1 C4 C9 24.9(3) . . . . ? O2 S1 C4 C9 155.6(2) . . . . ? N1 S1 C4 C9 -89.9(2) . . . . ? C9 C4 C5 C6 -1.1(4) . . . . ? S1 C4 C5 C6 -179.2(2) . . . . ? C4 C5 C6 C7 0.9(4) . . . . ? C5 C6 C7 C8 -0.2(5) . . . . ? C5 C6 C7 C10 -178.1(3) . . . . ? C6 C7 C8 C9 -0.3(5) . . . . ? C10 C7 C8 C9 177.6(3) . . . . ? C7 C8 C9 C4 0.1(5) . . . . ? C5 C4 C9 C8 0.6(4) . . . . ? S1 C4 C9 C8 178.7(2) . . . . ? O1 C1 C11 C12 67.8(3) . . . . ? N1 C1 C11 C12 -48.2(3) . . . . ? C1 C11 C12 C17 -90.7(3) . . . . ? C1 C11 C12 C13 86.7(3) . . . . ? C17 C12 C13 C14 2.0(4) . . . . ? C11 C12 C13 C14 -175.5(2) . . . . ? C12 C13 C14 C15 -0.9(4) . . . . ? C13 C14 C15 C16 -0.7(5) . . . . ? C14 C15 C16 C17 1.0(5) . . . . ? C15 C16 C17 C12 0.2(5) . . . . ? C13 C12 C17 C16 -1.7(4) . . . . ? C11 C12 C17 C16 175.8(3) . . . . ? #===END _database_code_depnum_ccdc_archive 'CCDC 942034' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_asb #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H27 N O3 S, C H Cl3' # Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)' _chemical_formula_structural ? _chemical_formula_sum 'C26 H28 Cl3 N O3 S' _chemical_formula_iupac ? _chemical_formula_weight 540.91 _chemical_compound_source 'see text' loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 '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' N N 0.0061 0.0033 '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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 1/2-x,-y,1/2+z 3 1/2+x,1/2-y,-z 4 -x,1/2+y,1/2-z _cell_length_a 8.413(1) _cell_length_b 14.850(2) _cell_length_c 21.756(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2718.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 295(1) _cell_measurement_reflns_used 15460 _cell_measurement_theta_min 2.6 _cell_measurement_theta_max 25.0 _cell_special_details ; ; _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.322 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_F_000 1128 _exptl_absorpt_coefficient_mu 0.441 _exptl_crystal_density_meas_temp ? _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction,2009)' _exptl_absorpt_correction_T_min 0.8790 _exptl_absorpt_correction_T_max 0.9169 #=============================================================================== # 7. EXPERIMENTAL DATA _exptl_special_details ; ; _diffrn_ambient_temperature 295(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_measurement_device_type 'Oxford Xcalibur,Eos(Nova) CCD detector' _diffrn_measurement_method 'f\w scans' _diffrn_reflns_number 15460 _diffrn_reflns_av_R_equivalents 0.1452 _diffrn_reflns_av_sigmaI/netI 0.1540 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.60 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_reduction_process ; ; # number of unique reflections _reflns_number_total 4718 # number of observed reflections (> n sig(I)) _reflns_number_gt 2307 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro CCD (Oxford Diffraction, 2009)' _computing_cell_refinement 'CrysAlisPro CCD (Oxford Diffraction, 2009)' _computing_data_reduction 'CrysAlisPro RED (Oxford Diffraction, 2009)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'WinGX (Farrugia, 1999)' #=============================================================================== # 8. REFINEMENT DATA _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^)+(0.0199P)^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_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.11(12) _chemical_absolute_configuration syn _refine_ls_number_reflns 4718 _refine_ls_number_parameters 309 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1637 _refine_ls_R_factor_gt 0.0768 _refine_ls_wR_factor_ref 0.1387 _refine_ls_wR_factor_gt 0.1077 _refine_ls_goodness_of_fit_ref 0.975 _refine_ls_restrained_S_all 0.975 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.283 _refine_diff_density_min -0.248 _refine_diff_density_rms 0.049 #=============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 S1 S 0.6635(2) 0.76612(12) 0.91274(7) 0.0478(4) Uani 1 1 d . . . O1 O 0.6966(5) 0.5492(3) 0.82702(18) 0.0529(12) Uani 1 1 d . . . O2 O 0.5288(5) 0.8105(3) 0.8852(2) 0.0573(13) Uani 1 1 d . . . O3 O 0.6902(5) 0.7731(3) 0.97704(17) 0.0643(13) Uani 1 1 d . . . N1 N 0.6429(5) 0.6594(3) 0.8981(2) 0.0387(13) Uani 1 1 d . . . C1 C 0.7515(7) 0.5930(4) 0.9278(3) 0.0438(17) Uani 1 1 d . . . H1 H 0.8344 0.6244 0.9510 0.053 Uiso 1 1 calc R . . C2 C 0.8228(8) 0.5491(4) 0.8706(3) 0.0562(19) Uani 1 1 d . . . H2A H 0.9127 0.5836 0.8556 0.067 Uiso 1 1 calc R . . H2B H 0.8575 0.4882 0.8794 0.067 Uiso 1 1 calc R . . C3 C 0.6177(7) 0.6322(4) 0.8332(3) 0.0450(17) Uani 1 1 d . . . H3 H 0.6675 0.6767 0.8060 0.054 Uiso 1 1 calc R . . C4 C 0.8350(8) 0.8036(4) 0.8741(3) 0.0414(15) Uani 1 1 d . . . C5 C 0.9822(7) 0.7922(4) 0.9011(3) 0.0465(17) Uani 1 1 d . . . H5 H 0.9910 0.7697 0.9408 0.056 Uiso 1 1 calc R . . C6 C 1.1177(8) 0.8152(4) 0.8673(3) 0.0549(19) Uani 1 1 d . . . H6 H 1.2175 0.8055 0.8845 0.066 Uiso 1 1 calc R . . C7 C 1.1077(8) 0.8513(5) 0.8098(3) 0.0556(19) Uani 1 1 d . . . C8 C 0.9563(9) 0.8627(5) 0.7840(3) 0.060(2) Uani 1 1 d . . . H8 H 0.9477 0.8865 0.7446 0.073 Uiso 1 1 calc R . . C9 C 0.8203(8) 0.8398(4) 0.8154(3) 0.0538(18) Uani 1 1 d . . . H9 H 0.7207 0.8483 0.7978 0.065 Uiso 1 1 calc R . . C10 C 1.2572(8) 0.8747(5) 0.7740(4) 0.091(3) Uani 1 1 d . . . H10A H 1.3449 0.8807 0.8019 0.137 Uiso 1 1 calc R . . H10B H 1.2415 0.9305 0.7525 0.137 Uiso 1 1 calc R . . H10C H 1.2796 0.8277 0.7449 0.137 Uiso 1 1 calc R . . C11 C 0.6598(7) 0.5300(4) 0.9697(3) 0.0492(17) Uani 1 1 d . . . H11A H 0.5996 0.5658 0.9988 0.059 Uiso 1 1 calc R . . H11B H 0.5844 0.4962 0.9451 0.059 Uiso 1 1 calc R . . C12 C 0.7606(7) 0.4658(5) 1.0042(3) 0.0442(17) Uani 1 1 d . . . C13 C 0.8617(8) 0.4949(5) 1.0503(3) 0.0573(19) Uani 1 1 d . . . H13 H 0.8668 0.5558 1.0599 0.069 Uiso 1 1 calc R . . C14 C 0.9558(9) 0.4337(7) 1.0826(3) 0.081(3) Uani 1 1 d . . . H14 H 1.0207 0.4544 1.1142 0.097 Uiso 1 1 calc R . . C15 C 0.9546(11) 0.3439(7) 1.0688(4) 0.096(3) Uani 1 1 d . . . H15 H 1.0186 0.3036 1.0901 0.115 Uiso 1 1 calc R . . C16 C 0.8569(11) 0.3153(6) 1.0227(4) 0.088(3) Uani 1 1 d . . . H16 H 0.8535 0.2545 1.0126 0.106 Uiso 1 1 calc R . . C17 C 0.7638(8) 0.3749(5) 0.9910(3) 0.061(2) Uani 1 1 d . . . H17 H 0.7001 0.3533 0.9593 0.074 Uiso 1 1 calc R . . C18 C 0.4425(7) 0.6208(5) 0.8151(3) 0.0522(18) Uani 1 1 d . . . H18 H 0.3904 0.6785 0.8239 0.063 Uiso 1 1 calc R . . C19 C 0.3593(8) 0.5519(5) 0.8530(3) 0.0486(17) Uani 1 1 d . . . C20 C 0.3610(8) 0.4624(5) 0.8389(3) 0.069(2) Uani 1 1 d . . . H20 H 0.4139 0.4434 0.8037 0.082 Uiso 1 1 calc R . . C21 C 0.2868(10) 0.3997(6) 0.8754(4) 0.083(3) Uani 1 1 d . . . H21 H 0.2896 0.3391 0.8646 0.099 Uiso 1 1 calc R . . C22 C 0.2079(10) 0.4262(7) 0.9279(5) 0.097(3) Uani 1 1 d . . . H22 H 0.1572 0.3841 0.9528 0.117 Uiso 1 1 calc R . . C23 C 0.2056(8) 0.5161(7) 0.9430(4) 0.080(3) Uani 1 1 d . . . H23 H 0.1529 0.5349 0.9783 0.096 Uiso 1 1 calc R . . C24 C 0.2799(7) 0.5780(5) 0.9066(3) 0.062(2) Uani 1 1 d . . . H24 H 0.2776 0.6385 0.9176 0.074 Uiso 1 1 calc R . . C25 C 0.4312(9) 0.6069(5) 0.7458(3) 0.087(3) Uani 1 1 d . . . H25A H 0.3229 0.5946 0.7347 0.131 Uiso 1 1 calc R . . H25B H 0.4970 0.5570 0.7340 0.131 Uiso 1 1 calc R . . H25C H 0.4666 0.6603 0.7250 0.131 Uiso 1 1 calc R . . C26 C -0.0227(9) 0.6364(6) 0.6347(4) 0.090(3) Uani 1 1 d . . . H26 H -0.1160 0.6436 0.6082 0.108 Uiso 1 1 calc R . . Cl1 Cl -0.0863(4) 0.6113(2) 0.70605(13) 0.1558(14) Uani 1 1 d . . . Cl2 Cl 0.0794(4) 0.73684(19) 0.63571(15) 0.1602(13) Uani 1 1 d . . . Cl3 Cl 0.0967(3) 0.55337(18) 0.60331(11) 0.1133(9) Uani 1 1 d . . . 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 S1 0.0421(10) 0.0538(11) 0.0475(10) -0.0044(9) 0.0046(9) -0.0029(9) O1 0.049(3) 0.067(3) 0.043(3) -0.011(2) -0.001(2) 0.005(2) O2 0.032(3) 0.056(3) 0.083(4) -0.005(3) 0.002(2) 0.003(2) O3 0.074(3) 0.081(4) 0.038(2) -0.015(3) 0.009(2) -0.015(3) N1 0.037(3) 0.047(3) 0.032(3) 0.004(2) 0.000(2) -0.006(3) C1 0.042(4) 0.045(4) 0.044(4) 0.004(3) -0.008(3) 0.004(3) C2 0.049(4) 0.061(5) 0.059(4) 0.014(4) 0.011(4) 0.021(4) C3 0.045(4) 0.049(4) 0.042(4) 0.002(3) 0.004(3) -0.003(3) C4 0.046(4) 0.038(4) 0.040(4) 0.002(3) -0.003(3) -0.003(3) C5 0.045(4) 0.050(4) 0.045(4) 0.003(4) -0.009(3) -0.005(3) C6 0.035(4) 0.055(5) 0.075(5) 0.007(4) -0.011(4) -0.010(3) C7 0.039(4) 0.062(5) 0.066(5) 0.018(4) 0.006(4) 0.004(4) C8 0.069(6) 0.065(5) 0.047(4) 0.021(4) -0.003(4) -0.004(4) C9 0.049(4) 0.062(5) 0.051(4) 0.009(4) -0.015(4) -0.013(4) C10 0.062(5) 0.115(8) 0.096(6) 0.036(6) 0.027(5) 0.003(5) C11 0.038(4) 0.062(5) 0.048(4) 0.008(4) 0.007(3) -0.016(4) C12 0.035(4) 0.054(5) 0.043(4) -0.002(4) 0.008(3) -0.004(3) C13 0.057(5) 0.068(5) 0.047(4) 0.007(4) 0.001(4) -0.007(4) C14 0.049(5) 0.143(9) 0.050(5) 0.027(6) -0.001(4) 0.007(6) C15 0.095(7) 0.112(9) 0.081(7) 0.036(7) 0.019(6) 0.053(7) C16 0.105(8) 0.069(6) 0.090(7) 0.022(6) 0.022(6) 0.033(6) C17 0.071(5) 0.057(5) 0.057(5) -0.001(4) -0.005(4) -0.001(4) C18 0.050(4) 0.065(5) 0.042(4) -0.001(4) -0.007(3) 0.005(4) C19 0.047(4) 0.057(5) 0.041(4) 0.004(4) -0.009(3) -0.010(4) C20 0.067(5) 0.073(6) 0.067(5) 0.002(5) -0.007(4) -0.023(5) C21 0.081(7) 0.062(6) 0.105(7) 0.004(6) -0.015(6) -0.033(5) C22 0.054(6) 0.114(9) 0.124(9) 0.040(8) -0.005(6) -0.025(6) C23 0.044(5) 0.117(8) 0.079(6) 0.020(6) 0.007(4) -0.012(5) C24 0.038(4) 0.081(6) 0.066(5) 0.016(5) 0.003(4) 0.002(4) C25 0.088(7) 0.123(8) 0.051(5) 0.010(5) -0.026(5) -0.028(6) C26 0.063(6) 0.127(8) 0.081(6) -0.016(6) 0.011(5) 0.005(6) Cl1 0.186(3) 0.162(3) 0.119(2) -0.006(2) 0.078(2) -0.016(3) Cl2 0.206(3) 0.097(2) 0.177(3) 0.023(2) 0.066(3) 0.003(2) Cl3 0.0901(18) 0.136(2) 0.1142(19) -0.0350(18) 0.0080(15) 0.0172(16) _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 S1 O3 1.421(4) . ? S1 O2 1.441(4) . ? S1 N1 1.625(5) . ? S1 C4 1.760(6) . ? O1 C3 1.406(7) . ? O1 C2 1.424(7) . ? N1 C3 1.484(7) . ? N1 C1 1.491(7) . ? C1 C11 1.517(7) . ? C1 C2 1.526(8) . ? C1 H1 0.9800 . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C18 1.536(8) . ? C3 H3 0.9800 . ? C4 C5 1.380(8) . ? C4 C9 1.391(8) . ? C5 C6 1.399(8) . ? C5 H5 0.9300 . ? C6 C7 1.364(9) . ? C6 H6 0.9300 . ? C7 C8 1.402(8) . ? C7 C10 1.520(9) . ? C8 C9 1.376(8) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.480(8) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C17 1.380(9) . ? C12 C13 1.385(8) . ? C13 C14 1.395(9) . ? C13 H13 0.9300 . ? C14 C15 1.367(11) . ? C14 H14 0.9300 . ? C15 C16 1.365(11) . ? C15 H15 0.9300 . ? C16 C17 1.368(9) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C19 1.489(8) . ? C18 C25 1.527(8) . ? C18 H18 0.9800 . ? C19 C20 1.364(9) . ? C19 C24 1.398(9) . ? C20 C21 1.374(9) . ? C20 H20 0.9300 . ? C21 C22 1.379(11) . ? C21 H21 0.9300 . ? C22 C23 1.374(11) . ? C22 H22 0.9300 . ? C23 C24 1.365(10) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 Cl1 1.684(8) . ? C26 Cl2 1.722(8) . ? C26 Cl3 1.730(8) . ? C26 H26 0.9800 . ? 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 O3 S1 O2 120.0(3) . . ? O3 S1 N1 106.3(3) . . ? O2 S1 N1 106.3(3) . . ? O3 S1 C4 108.5(3) . . ? O2 S1 C4 107.5(3) . . ? N1 S1 C4 107.6(3) . . ? C3 O1 C2 106.8(5) . . ? C3 N1 C1 108.6(4) . . ? C3 N1 S1 117.8(4) . . ? C1 N1 S1 119.6(4) . . ? N1 C1 C11 110.9(5) . . ? N1 C1 C2 99.9(4) . . ? C11 C1 C2 115.2(5) . . ? N1 C1 H1 110.2 . . ? C11 C1 H1 110.2 . . ? C2 C1 H1 110.2 . . ? O1 C2 C1 104.4(5) . . ? O1 C2 H2A 110.9 . . ? C1 C2 H2A 110.9 . . ? O1 C2 H2B 110.9 . . ? C1 C2 H2B 110.9 . . ? H2A C2 H2B 108.9 . . ? O1 C3 N1 105.2(5) . . ? O1 C3 C18 109.4(5) . . ? N1 C3 C18 114.2(5) . . ? O1 C3 H3 109.3 . . ? N1 C3 H3 109.3 . . ? C18 C3 H3 109.3 . . ? C5 C4 C9 121.2(6) . . ? C5 C4 S1 119.6(5) . . ? C9 C4 S1 119.2(5) . . ? C4 C5 C6 118.6(6) . . ? C4 C5 H5 120.7 . . ? C6 C5 H5 120.7 . . ? C7 C6 C5 121.8(6) . . ? C7 C6 H6 119.1 . . ? C5 C6 H6 119.1 . . ? C6 C7 C8 118.1(6) . . ? C6 C7 C10 120.6(6) . . ? C8 C7 C10 121.3(6) . . ? C9 C8 C7 121.8(6) . . ? C9 C8 H8 119.1 . . ? C7 C8 H8 119.1 . . ? C8 C9 C4 118.5(6) . . ? C8 C9 H9 120.7 . . ? C4 C9 H9 120.7 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C1 114.3(5) . . ? C12 C11 H11A 108.7 . . ? C1 C11 H11A 108.7 . . ? C12 C11 H11B 108.7 . . ? C1 C11 H11B 108.7 . . ? H11A C11 H11B 107.6 . . ? C17 C12 C13 116.3(6) . . ? C17 C12 C11 122.4(6) . . ? C13 C12 C11 121.2(6) . . ? C12 C13 C14 120.7(7) . . ? C12 C13 H13 119.6 . . ? C14 C13 H13 119.6 . . ? C15 C14 C13 121.3(8) . . ? C15 C14 H14 119.3 . . ? C13 C14 H14 119.3 . . ? C16 C15 C14 118.0(9) . . ? C16 C15 H15 121.0 . . ? C14 C15 H15 121.0 . . ? C15 C16 C17 120.9(9) . . ? C15 C16 H16 119.5 . . ? C17 C16 H16 119.5 . . ? C16 C17 C12 122.6(7) . . ? C16 C17 H17 118.7 . . ? C12 C17 H17 118.7 . . ? C19 C18 C25 115.2(6) . . ? C19 C18 C3 112.7(5) . . ? C25 C18 C3 109.1(5) . . ? C19 C18 H18 106.4 . . ? C25 C18 H18 106.4 . . ? C3 C18 H18 106.4 . . ? C20 C19 C24 117.6(7) . . ? C20 C19 C18 122.7(7) . . ? C24 C19 C18 119.7(6) . . ? C19 C20 C21 121.7(7) . . ? C19 C20 H20 119.2 . . ? C21 C20 H20 119.2 . . ? C20 C21 C22 120.2(8) . . ? C20 C21 H21 119.9 . . ? C22 C21 H21 119.9 . . ? C23 C22 C21 118.8(9) . . ? C23 C22 H22 120.6 . . ? C21 C22 H22 120.6 . . ? C24 C23 C22 120.7(9) . . ? C24 C23 H23 119.7 . . ? C22 C23 H23 119.7 . . ? C23 C24 C19 121.0(8) . . ? C23 C24 H24 119.5 . . ? C19 C24 H24 119.5 . . ? C18 C25 H25A 109.5 . . ? C18 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C18 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? Cl1 C26 Cl2 109.8(5) . . ? Cl1 C26 Cl3 113.0(5) . . ? Cl2 C26 Cl3 109.4(4) . . ? Cl1 C26 H26 108.2 . . ? Cl2 C26 H26 108.2 . . ? Cl3 C26 H26 108.2 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 S1 N1 C3 -178.3(4) . . . . ? O2 S1 N1 C3 52.7(5) . . . . ? C4 S1 N1 C3 -62.2(5) . . . . ? O3 S1 N1 C1 -42.7(5) . . . . ? O2 S1 N1 C1 -171.6(4) . . . . ? C4 S1 N1 C1 73.4(4) . . . . ? C3 N1 C1 C11 -104.3(5) . . . . ? S1 N1 C1 C11 116.5(5) . . . . ? C3 N1 C1 C2 17.7(6) . . . . ? S1 N1 C1 C2 -121.6(5) . . . . ? C3 O1 C2 C1 40.1(6) . . . . ? N1 C1 C2 O1 -34.3(6) . . . . ? C11 C1 C2 O1 84.5(6) . . . . ? C2 O1 C3 N1 -28.0(6) . . . . ? C2 O1 C3 C18 -151.1(5) . . . . ? C1 N1 C3 O1 5.0(6) . . . . ? S1 N1 C3 O1 145.2(4) . . . . ? C1 N1 C3 C18 125.0(6) . . . . ? S1 N1 C3 C18 -94.9(6) . . . . ? O3 S1 C4 C5 30.8(6) . . . . ? O2 S1 C4 C5 162.1(5) . . . . ? N1 S1 C4 C5 -83.8(5) . . . . ? O3 S1 C4 C9 -152.6(5) . . . . ? O2 S1 C4 C9 -21.4(6) . . . . ? N1 S1 C4 C9 92.8(5) . . . . ? C9 C4 C5 C6 -2.0(9) . . . . ? S1 C4 C5 C6 174.4(5) . . . . ? C4 C5 C6 C7 2.4(10) . . . . ? C5 C6 C7 C8 -1.8(11) . . . . ? C5 C6 C7 C10 -179.4(7) . . . . ? C6 C7 C8 C9 0.9(11) . . . . ? C10 C7 C8 C9 178.4(7) . . . . ? C7 C8 C9 C4 -0.5(11) . . . . ? C5 C4 C9 C8 1.1(10) . . . . ? S1 C4 C9 C8 -175.4(5) . . . . ? N1 C1 C11 C12 -176.1(5) . . . . ? C2 C1 C11 C12 71.5(7) . . . . ? C1 C11 C12 C17 -108.8(7) . . . . ? C1 C11 C12 C13 68.8(7) . . . . ? C17 C12 C13 C14 -2.4(9) . . . . ? C11 C12 C13 C14 179.9(6) . . . . ? C12 C13 C14 C15 1.8(11) . . . . ? C13 C14 C15 C16 -0.7(13) . . . . ? C14 C15 C16 C17 0.5(13) . . . . ? C15 C16 C17 C12 -1.2(12) . . . . ? C13 C12 C17 C16 2.2(10) . . . . ? C11 C12 C17 C16 179.9(6) . . . . ? O1 C3 C18 C19 58.4(7) . . . . ? N1 C3 C18 C19 -59.2(7) . . . . ? O1 C3 C18 C25 -70.8(7) . . . . ? N1 C3 C18 C25 171.6(6) . . . . ? C25 C18 C19 C20 40.0(9) . . . . ? C3 C18 C19 C20 -86.1(8) . . . . ? C25 C18 C19 C24 -142.2(6) . . . . ? C3 C18 C19 C24 91.7(7) . . . . ? C24 C19 C20 C21 0.5(11) . . . . ? C18 C19 C20 C21 178.4(6) . . . . ? C19 C20 C21 C22 -0.1(12) . . . . ? C20 C21 C22 C23 -0.1(13) . . . . ? C21 C22 C23 C24 0.0(13) . . . . ? C22 C23 C24 C19 0.4(11) . . . . ? C20 C19 C24 C23 -0.6(10) . . . . ? C18 C19 C24 C23 -178.5(6) . . . . ? #===END _database_code_depnum_ccdc_archive 'CCDC 942035'