# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_4d _database_code_depnum_ccdc_archive 'CCDC 904090' #TrackingRef 'Caselli_Dalton.cif' _audit_creation_date 2012-09-27T13:26:22-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C39 H44 N4 O4 S2' _chemical_formula_weight 696.9 _chemical_absolute_configuration rmad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 9.7670(4) _cell_length_b 14.2550(5) _cell_length_c 25.9891(15) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3618.4(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1674 _cell_measurement_theta_min 2.8521 _cell_measurement_theta_max 25.2949 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_size_max 0.1736 _exptl_crystal_size_mid 0.0842 _exptl_crystal_size_min 0.0834 _exptl_crystal_density_diffrn 1.279 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1480 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 -1 3 0.0426 0 1 -3 0.0426 2 1 0 0.0751 -2 -1 0 0.0701 -1 1 -1 0.0636 0 -3 5 0.041 -1 -1 0 0.0712 1 1 -1 0.0582 0 -3 -4 0.0512 1 2 4 0.0417 0 3 4 0.0329 -3 -2 -2 0.0565 0 -2 -1 0.0383 0 0 1 0.0317 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.193 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) Numerical absorption correction based on gaussian integration over a multifaceted crystal model ; _exptl_absorpt_correction_T_min 1.071 _exptl_absorpt_correction_T_max 1.172 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 16.0965 _diffrn_orient_matrix_ub_11 -0.0022231 _diffrn_orient_matrix_ub_12 -0.0496953 _diffrn_orient_matrix_ub_13 0.0011153 _diffrn_orient_matrix_ub_21 0.0358123 _diffrn_orient_matrix_ub_22 -0.0024968 _diffrn_orient_matrix_ub_23 -0.0237048 _diffrn_orient_matrix_ub_31 0.0631448 _diffrn_orient_matrix_ub_32 -0.0003094 _diffrn_orient_matrix_ub_33 0.0134748 _diffrn_measurement_device_type 'SuperNova, Single source at offset), Eos' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0495 _diffrn_reflns_av_unetI/netI 0.1259 _diffrn_reflns_number 11009 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.86 _diffrn_reflns_theta_max 25.35 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 6595 _reflns_number_gt 3421 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # 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^)+(0.0089P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 6595 _refine_ls_number_parameters 442 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1506 _refine_ls_R_factor_gt 0.068 _refine_ls_wR_factor_ref 0.09 _refine_ls_wR_factor_gt 0.0694 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.999 _refine_ls_shift/su_max 0.01 _refine_ls_shift/su_mean 0.001 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.05(9) _refine_diff_density_max 0.192 _refine_diff_density_min -0.171 _refine_diff_density_rms 0.041 #----------------------------------------------------------------------------# # 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' S S 0.1246 0.1234 '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 C11 C 0.4309(5) -0.0132(3) 0.8733(2) 0.0518(15) Uani 1 1 d . . . C401 C 0.3609(5) 0.0295(3) 0.9125(2) 0.0689(18) Uani 1 1 d . . . H401 H 0.376 0.0923 0.9202 0.083 Uiso 1 1 calc R . . C402 C 0.2672(6) -0.0225(4) 0.9403(3) 0.080(2) Uani 1 1 d . . . H402 H 0.2172 0.0046 0.9669 0.096 Uiso 1 1 calc R . . C403 C 0.2500(5) -0.1159(4) 0.9277(2) 0.0660(17) Uani 1 1 d . . . H403 H 0.1886 -0.1529 0.946 0.079 Uiso 1 1 calc R . . C1 C 0.3239(5) -0.1534(3) 0.8879(2) 0.0526(16) Uani 1 1 d . . . C2 C 0.3083(5) -0.2568(3) 0.8727(2) 0.0560(16) Uani 1 1 d . . . H2 H 0.2246 -0.2799 0.8892 0.067 Uiso 1 1 calc R . . C21 C 0.2896(5) -0.2689(3) 0.8152(2) 0.0749(19) Uani 1 1 d . . . H21A H 0.2122 -0.2327 0.804 0.112 Uiso 1 1 calc R . . H21B H 0.2743 -0.3339 0.8075 0.112 Uiso 1 1 calc R . . H21C H 0.3704 -0.2476 0.7977 0.112 Uiso 1 1 calc R . . N3 N 0.4244(3) -0.3100(2) 0.89524(15) 0.0436(11) Uani 1 1 d . . . C4 C 0.5621(4) -0.2985(3) 0.87228(19) 0.0437(13) Uani 1 1 d . . . H4B H 0.555 -0.261 0.8412 0.052 Uiso 1 1 calc R . . H4A H 0.598 -0.3595 0.8628 0.052 Uiso 1 1 calc R . . C5 C 0.6606(4) -0.2511(3) 0.90959(19) 0.0456(14) Uani 1 1 d . . . H5B H 0.6178 -0.1954 0.9238 0.055 Uiso 1 1 calc R . . H5A H 0.6808 -0.2935 0.9378 0.055 Uiso 1 1 calc R . . C10 C 0.5333(5) 0.0418(3) 0.8414(2) 0.0589(16) Uani 1 1 d . . . H10 H 0.5187 0.1084 0.849 0.071 Uiso 1 1 calc R . . C22 C 0.5132(5) 0.0294(3) 0.7833(2) 0.078(2) Uani 1 1 d . . . H22A H 0.4207 0.0451 0.7744 0.116 Uiso 1 1 calc R . . H22B H 0.5313 -0.0346 0.7741 0.116 Uiso 1 1 calc R . . H22C H 0.5751 0.07 0.7652 0.116 Uiso 1 1 calc R . . N9 N 0.6746(4) 0.0182(2) 0.85874(17) 0.0534(12) Uani 1 1 d . . . C8 C 0.7317(5) -0.0740(3) 0.8436(2) 0.0589(15) Uani 1 1 d . . . H8A H 0.7901 -0.0652 0.8138 0.071 Uiso 1 1 calc R . . H8B H 0.6568 -0.1146 0.8333 0.071 Uiso 1 1 calc R . . C7 C 0.8136(5) -0.1228(3) 0.8853(2) 0.0640(17) Uani 1 1 d . . . H7A H 0.9104 -0.1104 0.8804 0.077 Uiso 1 1 calc R . . H7B H 0.7873 -0.0985 0.9187 0.077 Uiso 1 1 calc R . . C101 C 0.3815(5) -0.4977(3) 0.88001(19) 0.0446(13) Uani 1 1 d . . . C102 C 0.4968(5) -0.5488(3) 0.8677(2) 0.0510(14) Uani 1 1 d . . . H102 H 0.5805 -0.5349 0.883 0.061 Uiso 1 1 calc R . . C103 C 0.4866(5) -0.6212(3) 0.8322(2) 0.0593(16) Uani 1 1 d . . . H103 H 0.5649 -0.6544 0.8232 0.071 Uiso 1 1 calc R . . C104 C 0.3635(6) -0.6451(3) 0.8102(2) 0.0575(16) Uani 1 1 d . . . C105 C 0.2499(5) -0.5914(3) 0.8232(2) 0.0633(16) Uani 1 1 d . . . H105 H 0.1658 -0.6058 0.8084 0.076 Uiso 1 1 calc R . . C106 C 0.2574(5) -0.5177(3) 0.8573(2) 0.0557(16) Uani 1 1 d . . . H106 H 0.1802 -0.4821 0.8648 0.067 Uiso 1 1 calc R . . C107 C 0.3522(5) -0.7269(3) 0.7739(2) 0.087(2) Uani 1 1 d . . . H10A H 0.2592 -0.7329 0.7624 0.13 Uiso 1 1 calc R . . H10B H 0.3793 -0.7833 0.7913 0.13 Uiso 1 1 calc R . . H10C H 0.4109 -0.7167 0.7448 0.13 Uiso 1 1 calc R . . C201 C 0.7252(5) 0.1527(3) 0.9284(2) 0.0533(15) Uani 1 1 d . . . C202 C 0.6579(6) 0.2351(4) 0.9313(3) 0.0775(19) Uani 1 1 d . . . H202 H 0.6354 0.2675 0.9014 0.093 Uiso 1 1 calc R . . C203 C 0.6224(6) 0.2711(4) 0.9787(3) 0.085(2) Uani 1 1 d . . . H203 H 0.578 0.3288 0.9801 0.102 Uiso 1 1 calc R . . C204 C 0.6495(5) 0.2262(4) 1.0230(3) 0.0634(17) Uani 1 1 d . . . C205 C 0.7189(7) 0.1427(4) 1.0189(3) 0.111(3) Uani 1 1 d . . . H205 H 0.7411 0.1099 1.0487 0.133 Uiso 1 1 calc R . . C206 C 0.7565(7) 0.1061(4) 0.9720(3) 0.101(2) Uani 1 1 d . . . H206 H 0.8034 0.0494 0.9703 0.122 Uiso 1 1 calc R . . C207 C 0.6113(6) 0.2636(3) 1.0750(2) 0.091(2) Uani 1 1 d . . . H20A H 0.6362 0.2188 1.101 0.137 Uiso 1 1 calc R . . H20B H 0.5144 0.2745 1.0763 0.137 Uiso 1 1 calc R . . H20C H 0.6589 0.3214 1.0811 0.137 Uiso 1 1 calc R . . C301 C 0.8937(5) -0.3834(3) 0.8882(2) 0.0497(14) Uani 1 1 d . . . C302 C 0.8802(5) -0.4497(3) 0.9262(2) 0.0648(16) Uani 1 1 d . . . H302 H 0.8813 -0.431 0.9605 0.078 Uiso 1 1 calc R . . C303 C 0.8649(5) -0.5451(4) 0.9144(3) 0.0723(19) Uani 1 1 d . . . H303 H 0.8542 -0.5884 0.9408 0.087 Uiso 1 1 calc R . . C304 C 0.8656(5) -0.5751(4) 0.8650(3) 0.076(2) Uani 1 1 d . . . H304 H 0.8548 -0.6385 0.8578 0.091 Uiso 1 1 calc R . . C305 C 0.8821(5) -0.5117(4) 0.8253(3) 0.0646(18) Uani 1 1 d . . . C306 C 0.8888(6) -0.5409(5) 0.7729(3) 0.090(2) Uani 1 1 d . . . H306 H 0.877 -0.6042 0.7654 0.108 Uiso 1 1 calc R . . C307 C 0.9117(7) -0.4805(6) 0.7339(3) 0.101(3) Uani 1 1 d . . . H307 H 0.9155 -0.5019 0.7001 0.121 Uiso 1 1 calc R . . C308 C 0.9297(6) -0.3851(5) 0.7450(3) 0.091(2) Uani 1 1 d . . . H308 H 0.9482 -0.3434 0.7184 0.109 Uiso 1 1 calc R . . C309 C 0.9204(5) -0.3520(4) 0.7945(3) 0.0667(18) Uani 1 1 d . . . H309 H 0.9288 -0.288 0.8006 0.08 Uiso 1 1 calc R . . C310 C 0.8984(5) -0.4134(4) 0.8360(2) 0.0537(14) Uani 1 1 d . . . C311 C 0.9096(5) -0.2794(3) 0.9019(2) 0.0484(14) Uani 1 1 d . . . H311 H 0.9883 -0.2565 0.8821 0.058 Uiso 1 1 calc R . . C312 C 0.9434(5) -0.2623(3) 0.9585(2) 0.0625(17) Uani 1 1 d . . . H31A H 0.9519 -0.1962 0.9645 0.094 Uiso 1 1 calc R . . H31B H 1.0282 -0.2928 0.9669 0.094 Uiso 1 1 calc R . . H31C H 0.8715 -0.2873 0.9796 0.094 Uiso 1 1 calc R . . N12 N 0.4112(4) -0.1033(3) 0.85963(16) 0.0501(11) Uani 1 1 d . . . N6 N 0.7888(4) -0.2248(2) 0.88361(16) 0.0470(11) Uani 1 1 d . . . O1 O 0.2631(3) -0.3972(2) 0.95042(13) 0.0633(11) Uani 1 1 d . . . O2 O 0.5134(3) -0.4270(2) 0.95664(13) 0.0594(10) Uani 1 1 d . . . O3 O 0.9126(3) 0.0679(2) 0.87317(15) 0.0743(12) Uani 1 1 d . . . O4 O 0.7533(4) 0.1813(2) 0.83051(14) 0.0822(13) Uani 1 1 d . . . S1 S 0.39431(13) -0.40685(8) 0.92617(6) 0.0513(4) Uani 1 1 d . . . S2 S 0.77725(16) 0.10728(10) 0.86797(7) 0.0639(4) 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 C11 0.044(3) 0.040(3) 0.071(5) 0.002(3) -0.002(3) 0.004(3) C401 0.074(4) 0.048(3) 0.085(5) -0.006(4) 0.012(4) 0.012(3) C402 0.073(4) 0.076(4) 0.090(6) -0.011(4) 0.023(4) 0.022(4) C403 0.048(3) 0.059(4) 0.091(5) 0.015(4) 0.014(4) 0.002(3) C1 0.039(3) 0.044(3) 0.075(5) 0.006(3) -0.003(3) 0.011(3) C2 0.034(3) 0.051(3) 0.083(5) 0.009(3) -0.002(3) -0.004(3) C21 0.079(4) 0.051(3) 0.095(6) 0.003(4) -0.025(4) -0.013(3) N3 0.028(2) 0.034(2) 0.068(3) 0.006(2) 0.000(2) 0.0003(18) C4 0.034(3) 0.039(3) 0.058(4) -0.002(3) 0.009(3) -0.005(2) C5 0.030(3) 0.047(3) 0.060(4) -0.005(3) 0.008(3) -0.002(2) C10 0.076(4) 0.026(3) 0.075(5) -0.007(3) -0.007(4) 0.001(3) C22 0.087(4) 0.065(4) 0.081(6) 0.012(4) 0.001(4) -0.001(3) N9 0.056(3) 0.034(2) 0.071(4) -0.005(2) 0.005(2) -0.008(2) C8 0.065(4) 0.037(3) 0.074(5) 0.000(3) 0.004(3) -0.004(3) C7 0.053(3) 0.044(3) 0.095(5) -0.001(3) -0.003(3) -0.010(3) C101 0.045(3) 0.038(3) 0.051(4) 0.001(3) -0.002(3) -0.001(3) C102 0.041(3) 0.053(3) 0.059(4) 0.000(3) -0.011(3) 0.002(3) C103 0.056(4) 0.055(4) 0.067(5) -0.008(3) -0.008(3) 0.011(3) C104 0.078(4) 0.037(3) 0.057(4) 0.005(3) -0.008(3) -0.004(3) C105 0.057(4) 0.058(3) 0.075(5) 0.004(4) -0.013(3) -0.014(3) C106 0.045(3) 0.049(3) 0.074(5) 0.001(3) 0.001(3) -0.002(3) C107 0.116(5) 0.067(4) 0.077(5) -0.011(4) -0.005(4) 0.003(4) C201 0.063(4) 0.029(3) 0.068(5) -0.002(3) 0.009(4) -0.003(3) C202 0.115(5) 0.054(4) 0.064(5) 0.003(4) 0.002(4) 0.021(3) C203 0.115(5) 0.056(4) 0.085(6) 0.005(4) 0.004(5) 0.037(4) C204 0.069(4) 0.044(3) 0.077(5) -0.006(4) 0.008(4) 0.004(3) C205 0.180(7) 0.081(5) 0.071(6) 0.011(4) 0.020(5) 0.057(5) C206 0.153(7) 0.068(4) 0.083(6) -0.005(5) 0.004(5) 0.060(5) C207 0.109(5) 0.070(4) 0.093(6) -0.013(4) 0.020(5) -0.003(4) C301 0.034(3) 0.051(3) 0.064(4) -0.011(3) -0.003(3) 0.011(3) C302 0.069(4) 0.055(3) 0.071(5) -0.009(4) -0.008(4) 0.006(3) C303 0.078(4) 0.059(4) 0.081(6) 0.004(4) 0.000(4) 0.011(3) C304 0.053(4) 0.052(4) 0.121(7) -0.012(5) -0.009(4) 0.010(3) C305 0.043(3) 0.068(4) 0.082(6) -0.022(4) -0.010(4) 0.011(3) C306 0.064(4) 0.113(6) 0.092(7) -0.046(5) -0.018(5) 0.008(4) C307 0.083(5) 0.145(8) 0.075(6) -0.049(6) -0.004(5) 0.019(6) C308 0.072(4) 0.121(6) 0.079(6) -0.001(5) 0.003(4) 0.006(5) C309 0.050(4) 0.079(4) 0.071(5) -0.010(4) -0.008(4) 0.004(3) C310 0.035(3) 0.054(4) 0.072(5) -0.006(3) -0.002(3) 0.012(3) C311 0.034(3) 0.052(3) 0.060(4) -0.010(3) 0.003(3) 0.005(3) C312 0.049(3) 0.060(3) 0.079(5) -0.021(3) -0.009(3) -0.004(3) N12 0.050(3) 0.035(2) 0.065(3) 0.003(2) 0.001(2) -0.004(2) N6 0.038(2) 0.038(2) 0.065(3) 0.001(2) 0.000(2) -0.004(2) O1 0.056(2) 0.057(2) 0.078(3) -0.004(2) 0.0287(19) -0.0065(19) O2 0.066(2) 0.056(2) 0.056(3) 0.001(2) -0.0125(19) -0.0008(18) O3 0.058(2) 0.062(2) 0.103(3) -0.027(2) 0.018(2) -0.019(2) O4 0.130(4) 0.047(2) 0.069(3) 0.006(2) 0.020(3) -0.029(2) S1 0.0491(8) 0.0424(7) 0.0625(10) 0.0011(8) 0.0051(8) -0.0038(7) S2 0.0763(10) 0.0430(8) 0.0725(12) -0.0078(9) 0.0152(9) -0.0168(8) #----------------------------------------------------------------------------# # 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 C11 N12 1.346(5) . ? C11 C401 1.370(7) . ? C11 C10 1.518(7) . ? C401 C402 1.382(6) . ? C402 C403 1.381(6) . ? C403 C1 1.369(7) . ? C1 N12 1.334(6) . ? C1 C2 1.533(6) . ? C2 N3 1.485(5) . ? C2 C21 1.516(7) . ? N3 C4 1.481(5) . ? N3 S1 1.624(3) . ? C4 C5 1.524(5) . ? C5 N6 1.471(5) . ? C10 N9 1.490(5) . ? C10 C22 1.531(7) . ? N9 C8 1.481(5) . ? N9 S2 1.636(4) . ? C8 C7 1.518(6) . ? C7 N6 1.474(5) . ? C101 C102 1.379(5) . ? C101 C106 1.378(6) . ? C101 S1 1.770(5) . ? C102 C103 1.387(6) . ? C103 C104 1.375(6) . ? C104 C105 1.390(6) . ? C104 C107 1.503(6) . ? C105 C106 1.376(6) . ? C201 C202 1.348(6) . ? C201 C206 1.347(7) . ? C201 S2 1.773(5) . ? C202 C203 1.378(7) . ? C203 C204 1.344(7) . ? C204 C205 1.373(6) . ? C204 C207 1.501(7) . ? C205 C206 1.377(7) . ? C301 C302 1.373(6) . ? C301 C310 1.425(7) . ? C301 C311 1.532(6) . ? C302 C303 1.403(6) . ? C303 C304 1.352(7) . ? C304 C305 1.382(7) . ? C305 C306 1.424(8) . ? C305 C310 1.437(7) . ? C306 C307 1.350(8) . ? C307 C308 1.402(8) . ? C308 C309 1.371(7) . ? C309 C310 1.405(7) . ? C311 N6 1.491(5) . ? C311 C312 1.528(6) . ? O1 S1 1.435(3) . ? O2 S1 1.436(3) . ? O3 S2 1.443(3) . ? O4 S2 1.454(4) . ? 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 N12 C11 C401 123.3(5) . . ? N12 C11 C10 116.3(5) . . ? C401 C11 C10 120.4(5) . . ? C11 C401 C402 118.8(5) . . ? C403 C402 C401 118.2(6) . . ? C1 C403 C402 119.5(5) . . ? N12 C1 C403 122.9(5) . . ? N12 C1 C2 115.9(5) . . ? C403 C1 C2 121.2(5) . . ? N3 C2 C21 115.0(4) . . ? N3 C2 C1 108.3(4) . . ? C21 C2 C1 112.1(5) . . ? C4 N3 C2 118.6(4) . . ? C4 N3 S1 117.3(3) . . ? C2 N3 S1 119.4(3) . . ? N3 C4 C5 111.5(4) . . ? N6 C5 C4 111.0(4) . . ? N9 C10 C11 109.1(4) . . ? N9 C10 C22 113.0(5) . . ? C11 C10 C22 113.2(4) . . ? C8 N9 C10 117.9(4) . . ? C8 N9 S2 119.8(3) . . ? C10 N9 S2 115.9(3) . . ? N9 C8 C7 114.5(4) . . ? N6 C7 C8 110.1(4) . . ? C102 C101 C106 120.6(5) . . ? C102 C101 S1 119.1(4) . . ? C106 C101 S1 120.3(4) . . ? C101 C102 C103 119.2(4) . . ? C104 C103 C102 121.7(5) . . ? C103 C104 C105 117.3(5) . . ? C103 C104 C107 121.2(5) . . ? C105 C104 C107 121.4(5) . . ? C106 C105 C104 122.3(5) . . ? C105 C106 C101 118.7(5) . . ? C202 C201 C206 119.5(6) . . ? C202 C201 S2 120.5(5) . . ? C206 C201 S2 120.0(4) . . ? C201 C202 C203 119.8(6) . . ? C204 C203 C202 122.6(5) . . ? C203 C204 C205 116.3(6) . . ? C203 C204 C207 123.6(5) . . ? C205 C204 C207 120.0(6) . . ? C204 C205 C206 121.9(7) . . ? C201 C206 C205 119.8(6) . . ? C302 C301 C310 118.8(5) . . ? C302 C301 C311 120.6(5) . . ? C310 C301 C311 120.6(5) . . ? C301 C302 C303 121.3(6) . . ? C304 C303 C302 120.9(6) . . ? C303 C304 C305 120.2(6) . . ? C304 C305 C306 121.8(6) . . ? C304 C305 C310 120.4(6) . . ? C306 C305 C310 117.7(6) . . ? C307 C306 C305 122.6(7) . . ? C306 C307 C308 119.0(8) . . ? C309 C308 C307 121.3(7) . . ? C308 C309 C310 121.0(6) . . ? C309 C310 C301 123.3(5) . . ? C309 C310 C305 118.4(6) . . ? C301 C310 C305 118.3(6) . . ? N6 C311 C312 113.2(4) . . ? N6 C311 C301 110.6(4) . . ? C312 C311 C301 113.5(5) . . ? C1 N12 C11 117.2(5) . . ? C5 N6 C7 112.2(4) . . ? C5 N6 C311 113.2(4) . . ? C7 N6 C311 112.1(3) . . ? O1 S1 O2 120.0(2) . . ? O1 S1 N3 107.34(19) . . ? O2 S1 N3 107.22(19) . . ? O1 S1 C101 107.7(2) . . ? O2 S1 C101 106.6(2) . . ? N3 S1 C101 107.4(2) . . ? O3 S2 O4 119.5(2) . . ? O3 S2 N9 105.9(2) . . ? O4 S2 N9 111.5(2) . . ? O3 S2 C201 108.8(2) . . ? O4 S2 C201 106.4(2) . . ? N9 S2 C201 103.7(2) . . ? data_4f _database_code_depnum_ccdc_archive 'CCDC 904091' #TrackingRef 'Caselli_Dalton.cif' _audit_creation_date 2012-09-27T14:06:22-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C43 H52 N4 O4 S2' _chemical_formula_weight 753.01 _chemical_absolute_configuration rmad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 11.7359(2) _cell_length_b 14.7577(2) _cell_length_c 23.1185(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 4004.01(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6208 _cell_measurement_theta_min 1.6337 _cell_measurement_theta_max 26.6474 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.249 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1608 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.18 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.81881 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_detector_area_resol_mean 16.0965 _diffrn_orient_matrix_ub_11 -0.0308301 _diffrn_orient_matrix_ub_12 0.0050835 _diffrn_orient_matrix_ub_13 0.0261875 _diffrn_orient_matrix_ub_21 -0.0436023 _diffrn_orient_matrix_ub_22 0.0234459 _diffrn_orient_matrix_ub_23 -0.0150841 _diffrn_orient_matrix_ub_31 -0.0283386 _diffrn_orient_matrix_ub_32 -0.0416323 _diffrn_orient_matrix_ub_33 -0.0052933 _diffrn_measurement_device_type 'SuperNova, Single source at offset), Eos' _diffrn_measurement_method '\w scans' _diffrn_reflns_av_R_equivalents 0.0513 _diffrn_reflns_av_unetI/netI 0.0553 _diffrn_reflns_number 29479 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 26.71 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 0.944 _reflns_number_total 7762 _reflns_number_gt 5536 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET) (compiled Jul 11 2012,15:38:31) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # 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^)+(0.0395P)^2^+0.1421P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 7762 _refine_ls_number_parameters 478 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0848 _refine_ls_R_factor_gt 0.0498 _refine_ls_wR_factor_ref 0.101 _refine_ls_wR_factor_gt 0.088 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _refine_ls_shift/su_max 0.001 _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 0.01(6) _refine_diff_density_max 0.136 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.036 #----------------------------------------------------------------------------# # 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' S S 0.1246 0.1234 '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 C309 C -0.1017(3) 1.0922(2) 1.01236(14) 0.0660(10) Uani 1 1 d . . . H309 H -0.1039 1.0358 0.9944 0.079 Uiso 1 1 calc R . . C308 C -0.1486(3) 1.1021(3) 1.06625(15) 0.0786(11) Uani 1 1 d . . . H308 H -0.1805 1.0522 1.0848 0.094 Uiso 1 1 calc R . . C307 C -0.1490(3) 1.1861(3) 1.09358(16) 0.0835(13) Uani 1 1 d . . . H307 H -0.1825 1.1923 1.1298 0.1 Uiso 1 1 calc R . . C306 C -0.1009(3) 1.2587(3) 1.06769(16) 0.0723(11) Uani 1 1 d . . . H306 H -0.1011 1.3143 1.0866 0.087 Uiso 1 1 calc R . . C305 C -0.0498(3) 1.2516(2) 1.01197(14) 0.0594(9) Uani 1 1 d . . . C304 C 0.0011(3) 1.3265(2) 0.98495(16) 0.0681(10) Uani 1 1 d . . . H304 H 0.0017 1.3823 1.0036 0.082 Uiso 1 1 calc R . . C303 C 0.0490(3) 1.3182(2) 0.93221(16) 0.0658(9) Uani 1 1 d . . . H303 H 0.0828 1.3683 0.9148 0.079 Uiso 1 1 calc R . . C302 C 0.0484(3) 1.2343(2) 0.90323(14) 0.0548(8) Uani 1 1 d . . . H302 H 0.081 1.2304 0.8667 0.066 Uiso 1 1 calc R . . C301 C 0.0012(3) 1.1584(2) 0.92732(12) 0.0474(7) Uani 1 1 d . . . C310 C -0.0499(2) 1.1662(2) 0.98343(13) 0.0519(8) Uani 1 1 d . . . C13 C -0.1217(2) 1.0620(2) 0.86554(13) 0.0578(8) Uani 1 1 d . . . H13A H -0.1789 1.0632 0.8952 0.087 Uiso 1 1 calc R . . H13B H -0.1269 1.0062 0.8445 0.087 Uiso 1 1 calc R . . H13C H -0.1333 1.112 0.8396 0.087 Uiso 1 1 calc R . . C12 C -0.0031(2) 1.06975(19) 0.89334(12) 0.0459(7) Uani 1 1 d . . . H12 H 0.0062 1.0195 0.9206 0.055 Uiso 1 1 calc R . . N6 N 0.09075(18) 1.06602(14) 0.85130(9) 0.0397(5) Uani 1 1 d . . . C5 C 0.2017(2) 1.05581(17) 0.87953(12) 0.0436(7) Uani 1 1 d . . . H5A H 0.2062 1.1009 0.91 0.052 Uiso 1 1 calc R . . H5B H 0.2598 1.071 0.8513 0.052 Uiso 1 1 calc R . . C4 C 0.2342(2) 0.96292(18) 0.90647(11) 0.0426(7) Uani 1 1 d . . . H4 H 0.1645 0.9266 0.9092 0.051 Uiso 1 1 calc R . . C16 C 0.2825(3) 0.9741(2) 0.96872(13) 0.0612(9) Uani 1 1 d . . . H16 H 0.3376 1.024 0.9683 0.073 Uiso 1 1 calc R . . C17 C 0.3424(4) 0.8899(3) 0.99144(15) 0.0917(13) Uani 1 1 d . . . H17A H 0.405 0.875 0.9664 0.138 Uiso 1 1 calc R . . H17B H 0.2896 0.8403 0.9925 0.138 Uiso 1 1 calc R . . H17C H 0.3705 0.9014 1.0297 0.138 Uiso 1 1 calc R . . N3 N 0.31631(19) 0.91259(13) 0.86895(9) 0.0436(6) Uani 1 1 d . . . C2 C 0.4274(2) 0.9536(2) 0.85593(14) 0.0548(8) Uani 1 1 d . . . H2A H 0.4863 0.9086 0.8624 0.066 Uiso 1 1 calc R . . H2B H 0.4406 1.003 0.8828 0.066 Uiso 1 1 calc R . . C1 C 0.4391(3) 0.9897(2) 0.79474(14) 0.0547(8) Uani 1 1 d . . . N12 N 0.34242(19) 1.00858(15) 0.76781(11) 0.0481(6) Uani 1 1 d . . . C11 C 0.3465(2) 1.0434(2) 0.71445(13) 0.0512(8) Uani 1 1 d . . . C401 C 0.4480(3) 1.0593(3) 0.68615(17) 0.0780(11) Uani 1 1 d . . . H401 H 0.449 1.0827 0.6488 0.094 Uiso 1 1 calc R . . C402 C 0.5472(3) 1.0397(3) 0.71463(19) 0.0952(14) Uani 1 1 d . . . H402 H 0.6168 1.0504 0.6967 0.114 Uiso 1 1 calc R . . C403 C 0.5447(3) 1.0045(3) 0.76929(19) 0.0815(11) Uani 1 1 d . . . H403 H 0.6118 0.9908 0.7889 0.098 Uiso 1 1 calc R . . C10 C 0.2328(2) 1.0594(2) 0.68649(13) 0.0500(8) Uani 1 1 d . . . H10A H 0.245 1.0909 0.6502 0.06 Uiso 1 1 calc R . . H10B H 0.199 1.0011 0.6775 0.06 Uiso 1 1 calc R . . N9 N 0.15056(18) 1.11189(14) 0.72115(9) 0.0415(6) Uani 1 1 d . . . C8 C 0.0457(2) 1.06755(17) 0.74512(11) 0.0380(6) Uani 1 1 d . . . H8 H -0.005 1.1162 0.7581 0.046 Uiso 1 1 calc R . . C29 C -0.0189(2) 1.01412(19) 0.69794(12) 0.0470(7) Uani 1 1 d . . . H29 H 0.0245 0.9591 0.6891 0.056 Uiso 1 1 calc R . . C30 C -0.1369(2) 0.9863(2) 0.71886(14) 0.0656(9) Uani 1 1 d . . . H30A H -0.1298 0.9513 0.7537 0.098 Uiso 1 1 calc R . . H30B H -0.1736 0.9505 0.6896 0.098 Uiso 1 1 calc R . . H30C H -0.1815 1.0395 0.7265 0.098 Uiso 1 1 calc R . . C31 C -0.0323(3) 1.0688(2) 0.64232(13) 0.0669(9) Uani 1 1 d . . . H31A H -0.0689 1.0322 0.6135 0.1 Uiso 1 1 calc R . . H31B H 0.0415 1.0871 0.6287 0.1 Uiso 1 1 calc R . . H31C H -0.0778 1.1216 0.6498 0.1 Uiso 1 1 calc R . . C7 C 0.0759(2) 1.01082(17) 0.79871(11) 0.0385(7) Uani 1 1 d . . . H7A H 0.0159 0.9668 0.8054 0.046 Uiso 1 1 calc R . . H7B H 0.1458 0.9778 0.7912 0.046 Uiso 1 1 calc R . . C33 C 0.1873(4) 0.9988(3) 1.01020(14) 0.1042(15) Uani 1 1 d . . . H33A H 0.151 1.0535 0.9973 0.156 Uiso 1 1 calc R . . H33B H 0.2183 1.0079 1.0482 0.156 Uiso 1 1 calc R . . H33C H 0.1324 0.9506 1.0113 0.156 Uiso 1 1 calc R . . C101 C 0.2980(2) 0.79317(18) 0.78073(12) 0.0477(7) Uani 1 1 d . . . C102 C 0.3984(3) 0.7820(2) 0.74952(14) 0.0672(10) Uani 1 1 d . . . H102 H 0.4678 0.777 0.7687 0.081 Uiso 1 1 calc R . . C103 C 0.3946(3) 0.7785(3) 0.69076(15) 0.0729(10) Uani 1 1 d . . . H103 H 0.4621 0.7714 0.6701 0.088 Uiso 1 1 calc R . . C104 C 0.2922(3) 0.7852(2) 0.66078(13) 0.0610(9) Uani 1 1 d . . . C105 C 0.1931(3) 0.79391(19) 0.69255(13) 0.0546(8) Uani 1 1 d . . . H105 H 0.1235 0.7967 0.6734 0.065 Uiso 1 1 calc R . . C106 C 0.1955(3) 0.79865(18) 0.75210(12) 0.0495(7) Uani 1 1 d . . . H106 H 0.1281 0.8055 0.7728 0.059 Uiso 1 1 calc R . . C107 C 0.2908(3) 0.7821(3) 0.59566(15) 0.0896(12) Uani 1 1 d . . . H10A H 0.3673 0.7754 0.5815 0.134 Uiso 0.5 1 calc PR . . H10B H 0.2587 0.8373 0.5809 0.134 Uiso 0.5 1 calc PR . . H10C H 0.2456 0.7316 0.583 0.134 Uiso 0.5 1 calc PR . . H10D H 0.2138 0.7874 0.5821 0.134 Uiso 0.5 1 calc PR . . H10E H 0.3224 0.7256 0.5827 0.134 Uiso 0.5 1 calc PR . . H10F H 0.3354 0.8313 0.5806 0.134 Uiso 0.5 1 calc PR . . C201 C 0.1960(3) 1.26411(17) 0.66108(12) 0.0466(7) Uani 1 1 d . . . C202 C 0.3047(3) 1.2730(2) 0.63862(14) 0.0631(8) Uani 1 1 d . . . H202 H 0.3673 1.2562 0.6608 0.076 Uiso 1 1 calc R . . C203 C 0.3208(3) 1.3062(2) 0.58375(15) 0.0703(10) Uani 1 1 d . . . H203 H 0.3942 1.3109 0.5689 0.084 Uiso 1 1 calc R . . C204 C 0.2295(4) 1.3327(2) 0.55057(14) 0.0640(9) Uani 1 1 d . . . C205 C 0.1211(3) 1.3226(2) 0.57322(14) 0.0635(9) Uani 1 1 d . . . H205 H 0.0585 1.339 0.5509 0.076 Uiso 1 1 calc R . . C206 C 0.1036(3) 1.28866(18) 0.62828(13) 0.0537(8) Uani 1 1 d . . . H206 H 0.0301 1.2826 0.6429 0.064 Uiso 1 1 calc R . . C207 C 0.2471(4) 1.3695(2) 0.48953(15) 0.0968(14) Uani 1 1 d . . . H20A H 0.1745 1.3846 0.4729 0.145 Uiso 1 1 calc R . . H20B H 0.2838 1.3243 0.4662 0.145 Uiso 1 1 calc R . . H20C H 0.2939 1.4228 0.4911 0.145 Uiso 1 1 calc R . . O11 O 0.40139(19) 0.75733(14) 0.87577(9) 0.0642(6) Uani 1 1 d . . . O12 O 0.19233(17) 0.77836(12) 0.87915(8) 0.0577(5) Uani 1 1 d . . . O21 O 0.28535(18) 1.22853(14) 0.76023(9) 0.0633(6) Uani 1 1 d . . . O22 O 0.07850(18) 1.25952(12) 0.75641(8) 0.0570(6) Uani 1 1 d . . . S1 S 0.30162(7) 0.80440(5) 0.85651(3) 0.0500(2) Uani 1 1 d . . . S2 S 0.17774(7) 1.21860(5) 0.73137(3) 0.04724(19) 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 C309 0.070(2) 0.078(2) 0.051(2) -0.0114(19) 0.0103(18) 0.0050(19) C308 0.076(3) 0.108(3) 0.052(2) -0.010(2) 0.0175(19) 0.003(2) C307 0.064(3) 0.137(4) 0.049(2) -0.024(3) 0.0104(19) 0.020(3) C306 0.059(2) 0.097(3) 0.061(2) -0.032(2) -0.0063(19) 0.020(2) C305 0.051(2) 0.073(2) 0.054(2) -0.0191(18) -0.0048(17) 0.0182(17) C304 0.066(2) 0.058(2) 0.080(3) -0.019(2) -0.010(2) 0.0155(19) C303 0.068(2) 0.0452(19) 0.084(3) 0.0000(18) 0.002(2) 0.0072(17) C302 0.058(2) 0.0537(19) 0.053(2) 0.0002(16) 0.0014(16) 0.0080(16) C301 0.0521(18) 0.0504(18) 0.0397(17) -0.0043(14) 0.0016(15) 0.0081(15) C310 0.0465(19) 0.063(2) 0.0465(18) -0.0090(17) -0.0043(15) 0.0087(15) C13 0.0446(19) 0.073(2) 0.056(2) -0.0116(17) 0.0115(16) -0.0037(15) C12 0.0507(18) 0.0496(17) 0.0375(16) -0.0001(13) 0.0034(14) 0.0044(14) N6 0.0389(13) 0.0479(13) 0.0322(13) -0.0061(11) -0.0016(11) 0.0035(10) C5 0.0451(18) 0.0454(15) 0.0404(16) -0.0040(13) -0.0053(14) -0.0018(14) C4 0.0477(18) 0.0429(16) 0.0371(16) -0.0033(13) -0.0058(13) 0.0022(13) C16 0.084(3) 0.0568(19) 0.0422(19) -0.0026(15) -0.0222(17) 0.0095(17) C17 0.130(4) 0.093(3) 0.052(2) 0.001(2) -0.031(2) 0.037(3) N3 0.0401(13) 0.0422(12) 0.0486(14) -0.0025(11) -0.0036(12) -0.0005(11) C2 0.0373(18) 0.0555(18) 0.072(2) 0.0057(17) -0.0111(16) -0.0016(14) C1 0.045(2) 0.0525(18) 0.066(2) 0.0024(16) 0.0009(17) -0.0024(15) N12 0.0405(15) 0.0507(14) 0.0530(16) 0.0045(13) 0.0021(13) 0.0015(11) C11 0.0438(19) 0.0553(18) 0.054(2) 0.0010(16) 0.0102(15) 0.0042(14) C401 0.052(2) 0.108(3) 0.074(3) 0.022(2) 0.017(2) 0.006(2) C402 0.048(2) 0.136(4) 0.102(3) 0.035(3) 0.024(2) 0.002(2) C403 0.039(2) 0.106(3) 0.100(3) 0.029(3) 0.003(2) 0.0015(19) C10 0.058(2) 0.0507(17) 0.0414(18) -0.0007(14) 0.0096(15) 0.0025(15) N9 0.0468(14) 0.0393(12) 0.0384(13) -0.0021(10) 0.0049(11) 0.0009(10) C8 0.0384(16) 0.0398(15) 0.0358(16) -0.0005(12) -0.0003(13) 0.0049(12) C29 0.0492(19) 0.0472(17) 0.0445(17) -0.0044(14) -0.0091(14) 0.0091(14) C30 0.051(2) 0.079(2) 0.066(2) -0.0100(19) -0.0150(17) -0.0047(17) C31 0.083(2) 0.068(2) 0.049(2) 0.0032(17) -0.0218(19) -0.0007(18) C7 0.0379(17) 0.0394(15) 0.0383(16) -0.0002(13) 0.0008(12) 0.0008(13) C33 0.151(4) 0.125(3) 0.036(2) -0.013(2) -0.015(2) 0.056(3) C101 0.0492(19) 0.0468(16) 0.0472(17) -0.0075(14) -0.0028(15) 0.0019(15) C102 0.047(2) 0.091(3) 0.064(2) -0.016(2) -0.0036(17) 0.0082(19) C103 0.053(2) 0.108(3) 0.059(2) -0.018(2) 0.0052(18) 0.002(2) C104 0.066(2) 0.068(2) 0.0489(19) -0.0127(16) 0.0033(17) -0.0069(18) C105 0.0485(19) 0.0606(19) 0.0546(19) -0.0130(16) -0.0072(16) -0.0033(17) C106 0.0441(17) 0.0486(16) 0.0558(19) -0.0135(14) 0.0052(15) -0.0017(15) C107 0.091(3) 0.119(3) 0.058(2) -0.007(2) 0.005(2) -0.012(3) C201 0.0499(19) 0.0432(15) 0.0466(17) 0.0019(13) -0.0047(15) -0.0094(14) C202 0.054(2) 0.074(2) 0.062(2) 0.0095(18) -0.0058(18) -0.0182(17) C203 0.072(2) 0.074(2) 0.065(2) 0.0045(19) 0.010(2) -0.023(2) C204 0.099(3) 0.0444(18) 0.049(2) -0.0023(16) 0.012(2) -0.0071(18) C205 0.084(3) 0.056(2) 0.051(2) 0.0023(17) -0.0072(19) 0.0091(18) C206 0.060(2) 0.0486(18) 0.052(2) 0.0038(16) 0.0046(16) 0.0049(16) C207 0.172(4) 0.068(2) 0.050(2) 0.0099(19) 0.021(3) 0.000(3) O11 0.0694(15) 0.0594(13) 0.0638(15) -0.0026(11) -0.0153(12) 0.0245(11) O12 0.0630(14) 0.0528(12) 0.0572(13) -0.0040(10) 0.0078(11) -0.0100(11) O21 0.0640(14) 0.0708(13) 0.0550(13) -0.0065(11) -0.0228(11) -0.0119(11) O22 0.0727(15) 0.0464(11) 0.0520(13) -0.0058(10) 0.0122(11) 0.0056(10) S1 0.0553(5) 0.0460(4) 0.0487(5) -0.0020(4) -0.0041(4) 0.0055(4) S2 0.0558(5) 0.0470(4) 0.0390(4) -0.0007(3) -0.0026(4) -0.0035(4) #----------------------------------------------------------------------------# # 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 C309 C308 1.370(4) . ? C309 C310 1.418(4) . ? C308 C307 1.392(5) . ? C307 C306 1.350(5) . ? C306 C305 1.425(5) . ? C305 C304 1.402(5) . ? C305 C310 1.422(4) . ? C304 C303 1.348(4) . ? C303 C302 1.407(4) . ? C302 C301 1.368(4) . ? C301 C310 1.434(4) . ? C301 C12 1.527(4) . ? C13 C12 1.537(4) . ? C12 N6 1.470(3) . ? N6 C5 1.465(3) . ? N6 C7 1.474(3) . ? C5 C4 1.553(4) . ? C4 N3 1.494(3) . ? C4 C16 1.556(4) . ? C16 C33 1.517(5) . ? C16 C17 1.521(4) . ? N3 C2 1.469(3) . ? N3 S1 1.631(2) . ? C2 C1 1.518(4) . ? C1 N12 1.323(4) . ? C1 C403 1.390(4) . ? N12 C11 1.337(4) . ? C11 C401 1.379(4) . ? C11 C10 1.502(4) . ? C401 C402 1.368(5) . ? C402 C403 1.367(5) . ? C10 N9 1.474(3) . ? N9 C8 1.500(3) . ? N9 S2 1.624(2) . ? C8 C7 1.537(3) . ? C8 C29 1.545(4) . ? C29 C30 1.523(4) . ? C29 C31 1.526(4) . ? C101 C106 1.375(4) . ? C101 C102 1.392(4) . ? C101 S1 1.760(3) . ? C102 C103 1.360(4) . ? C103 C104 1.391(4) . ? C104 C105 1.382(4) . ? C104 C107 1.506(4) . ? C105 C106 1.379(4) . ? C201 C206 1.372(4) . ? C201 C202 1.383(4) . ? C201 S2 1.771(3) . ? C202 C203 1.373(4) . ? C203 C204 1.374(5) . ? C204 C205 1.384(5) . ? C204 C207 1.526(4) . ? C205 C206 1.383(4) . ? O11 S1 1.432(2) . ? O12 S1 1.438(2) . ? O21 S2 1.436(2) . ? O22 S2 1.434(2) . ? 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 C308 C309 C310 121.2(3) . . ? C309 C308 C307 120.6(4) . . ? C306 C307 C308 120.3(3) . . ? C307 C306 C305 121.3(4) . . ? C304 C305 C310 119.4(3) . . ? C304 C305 C306 121.6(3) . . ? C310 C305 C306 118.9(4) . . ? C303 C304 C305 120.6(3) . . ? C304 C303 C302 120.5(3) . . ? C301 C302 C303 121.9(3) . . ? C302 C301 C310 118.1(3) . . ? C302 C301 C12 120.4(3) . . ? C310 C301 C12 121.4(3) . . ? C309 C310 C305 117.7(3) . . ? C309 C310 C301 122.9(3) . . ? C305 C310 C301 119.4(3) . . ? N6 C12 C301 110.3(2) . . ? N6 C12 C13 113.5(2) . . ? C301 C12 C13 108.0(2) . . ? C5 N6 C12 112.1(2) . . ? C5 N6 C7 114.6(2) . . ? C12 N6 C7 118.5(2) . . ? N6 C5 C4 119.2(2) . . ? N3 C4 C5 111.3(2) . . ? N3 C4 C16 110.8(2) . . ? C5 C4 C16 111.5(2) . . ? C33 C16 C17 108.6(3) . . ? C33 C16 C4 110.0(3) . . ? C17 C16 C4 113.7(3) . . ? C2 N3 C4 119.1(2) . . ? C2 N3 S1 117.45(19) . . ? C4 N3 S1 121.37(18) . . ? N3 C2 C1 114.6(2) . . ? N12 C1 C403 122.2(3) . . ? N12 C1 C2 115.8(3) . . ? C403 C1 C2 122.0(3) . . ? C1 N12 C11 118.9(3) . . ? N12 C11 C401 122.3(3) . . ? N12 C11 C10 115.2(3) . . ? C401 C11 C10 122.5(3) . . ? C402 C401 C11 118.1(3) . . ? C403 C402 C401 120.5(3) . . ? C402 C403 C1 118.0(3) . . ? N9 C10 C11 115.5(2) . . ? C10 N9 C8 120.6(2) . . ? C10 N9 S2 117.39(18) . . ? C8 N9 S2 122.03(17) . . ? N9 C8 C7 110.3(2) . . ? N9 C8 C29 111.4(2) . . ? C7 C8 C29 113.8(2) . . ? C30 C29 C31 108.5(2) . . ? C30 C29 C8 111.1(2) . . ? C31 C29 C8 112.0(2) . . ? N6 C7 C8 113.0(2) . . ? C106 C101 C102 119.9(3) . . ? C106 C101 S1 119.6(2) . . ? C102 C101 S1 120.4(2) . . ? C103 C102 C101 119.6(3) . . ? C102 C103 C104 121.5(3) . . ? C105 C104 C103 118.0(3) . . ? C105 C104 C107 121.6(3) . . ? C103 C104 C107 120.4(3) . . ? C106 C105 C104 121.2(3) . . ? C101 C106 C105 119.7(3) . . ? C206 C201 C202 119.8(3) . . ? C206 C201 S2 120.7(2) . . ? C202 C201 S2 119.5(2) . . ? C203 C202 C201 120.5(3) . . ? C202 C203 C204 120.7(3) . . ? C203 C204 C205 118.3(3) . . ? C203 C204 C207 120.8(4) . . ? C205 C204 C207 120.8(4) . . ? C206 C205 C204 121.6(3) . . ? C201 C206 C205 119.1(3) . . ? O11 S1 O12 119.12(13) . . ? O11 S1 N3 109.48(13) . . ? O12 S1 N3 106.96(12) . . ? O11 S1 C101 106.47(14) . . ? O12 S1 C101 108.40(13) . . ? N3 S1 C101 105.67(12) . . ? O22 S2 O21 118.93(13) . . ? O22 S2 N9 107.91(12) . . ? O21 S2 N9 109.83(12) . . ? O22 S2 C201 108.01(13) . . ? O21 S2 C201 106.32(14) . . ? N9 S2 C201 104.95(12) . . ? data_5d _database_code_depnum_ccdc_archive 'CCDC 904092' #TrackingRef 'Caselli_Dalton.cif' _audit_creation_date 2012-10-02T23:52:23-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C38 H41 F3 N4 O7 S3' _chemical_formula_weight 818.93 _chemical_absolute_configuration rmad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 11.1014(6) _cell_length_b 12.1313(7) _cell_length_c 29.7535(17) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 4007.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_size_max 0.1500 _exptl_crystal_size_mid 0.1000 _exptl_crystal_size_min 0.0800 _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1712 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.251 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.0332 _diffrn_reflns_av_unetI/netI 0.034 _diffrn_reflns_number 33721 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 1.37 _diffrn_reflns_theta_max 27.02 _diffrn_reflns_theta_full 25 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 0.999 _reflns_number_total 8742 _reflns_number_gt 6124 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # 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^)+(0.1470P)^2^+1.6658P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 8742 _refine_ls_number_parameters 473 _refine_ls_number_restraints 31 _refine_ls_R_factor_all 0.1016 _refine_ls_R_factor_gt 0.0728 _refine_ls_wR_factor_ref 0.2337 _refine_ls_wR_factor_gt 0.2067 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_restrained_S_all 0.997 _refine_ls_shift/su_max 0.024 _refine_ls_shift/su_mean 0.001 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.03(11) _refine_diff_density_max 0.645 _refine_diff_density_min -0.571 _refine_diff_density_rms 0.077 #----------------------------------------------------------------------------# # 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _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 C11 C 0.8216(4) 0.7905(4) 0.18545(15) 0.0534(10) Uani 1 1 d . . . C401 C 0.7907(5) 0.6807(4) 0.1851(2) 0.0737(14) Uani 1 1 d . . . H401 H 0.7957 0.6402 0.1586 0.088 Uiso 1 1 calc R . . C402 C 0.7530(6) 0.6324(4) 0.2233(2) 0.0846(18) Uani 1 1 d . . . H402 H 0.7296 0.5588 0.2232 0.102 Uiso 1 1 calc R . . C403 C 0.7492(5) 0.6924(4) 0.2627(2) 0.0760(15) Uani 1 1 d . . . H403 H 0.7246 0.66 0.2895 0.091 Uiso 1 1 calc R . . C1 C 0.7828(4) 0.8011(4) 0.26112(16) 0.0553(10) Uani 1 1 d . . . C10 C 0.8580(5) 0.8498(4) 0.14297(16) 0.0604(11) Uani 1 1 d . . . H10A H 0.8879 0.796 0.1216 0.072 Uiso 1 1 calc R . . H10B H 0.7871 0.8839 0.13 0.072 Uiso 1 1 calc R . . C8 C 0.9224(4) 1.0513(4) 0.14210(13) 0.0534(10) Uani 1 1 d . . . H8A H 0.8424 1.0573 0.1293 0.064 Uiso 1 1 calc R . . H8B H 0.9791 1.0814 0.1205 0.064 Uiso 1 1 calc R . . C7 C 0.9277(4) 1.1193(3) 0.18495(13) 0.0491(9) Uani 1 1 d . . . H7A H 1.0065 1.1099 0.1985 0.059 Uiso 1 1 calc R . . H7B H 0.9192 1.1965 0.1771 0.059 Uiso 1 1 calc R . . C2 C 0.7882(5) 0.8693(4) 0.30311(15) 0.0595(11) Uani 1 1 d . . . H2A H 0.7504 0.8289 0.3275 0.071 Uiso 1 1 calc R . . H2B H 0.8718 0.8814 0.3111 0.071 Uiso 1 1 calc R . . C4 C 0.8016(4) 1.0754(4) 0.30405(13) 0.0512(9) Uani 1 1 d . . . H4A H 0.8464 1.069 0.3319 0.061 Uiso 1 1 calc R . . H4B H 0.7496 1.1394 0.3064 0.061 Uiso 1 1 calc R . . C5 C 0.8890(4) 1.0923(4) 0.26571(12) 0.0470(9) Uani 1 1 d . . . H5A H 0.9499 1.0351 0.2672 0.056 Uiso 1 1 calc R . . H5B H 0.9293 1.1624 0.2699 0.056 Uiso 1 1 calc R . . C31 C 0.6667(4) 1.1524(4) 0.16829(14) 0.0517(10) Uani 1 1 d . . . C32 C 0.6895(5) 1.2297(5) 0.13606(16) 0.0676(13) Uani 1 1 d . . . H32 H 0.7334 1.2924 0.1435 0.081 Uiso 1 1 calc R . . C33 C 0.6475(6) 1.2160(6) 0.09174(19) 0.0863(19) Uani 1 1 d . . . H33 H 0.6634 1.2696 0.0702 0.104 Uiso 1 1 calc R . . C34 C 0.5843(6) 1.1252(6) 0.08049(18) 0.0875(19) Uani 1 1 d . . . H34 H 0.5592 1.1157 0.0509 0.105 Uiso 1 1 calc R . . C35 C 0.5562(5) 1.0459(5) 0.11222(19) 0.0783(16) Uani 1 1 d . . . C36 C 0.4883(7) 0.9511(9) 0.1012(3) 0.115(3) Uani 1 1 d . . . H36 H 0.4618 0.9421 0.0718 0.138 Uiso 1 1 calc R . . C37 C 0.4609(8) 0.8737(8) 0.1317(4) 0.131(3) Uani 1 1 d . . . H37 H 0.4153 0.813 0.123 0.157 Uiso 1 1 calc R . . C38 C 0.5008(6) 0.8826(7) 0.1777(3) 0.108(2) Uani 1 1 d . . . H38 H 0.4819 0.8292 0.199 0.129 Uiso 1 1 calc R . . C39 C 0.5677(4) 0.9737(5) 0.1885(2) 0.0729(14) Uani 1 1 d . . . H39 H 0.5957 0.9806 0.2178 0.088 Uiso 1 1 calc R . . C111 C 1.1201(4) 0.8780(4) 0.08732(14) 0.0541(10) Uani 1 1 d . . . C112 C 1.1681(5) 0.9626(4) 0.06116(18) 0.0677(12) Uani 1 1 d . . . H112 H 1.1869 1.0305 0.0738 0.081 Uiso 1 1 calc R . . C113 C 1.1870(5) 0.9432(5) 0.01642(18) 0.0808(16) Uani 1 1 d . . . H113 H 1.2217 0.9988 -0.0008 0.097 Uiso 1 1 calc R . . C114 C 1.1582(6) 0.8483(6) -0.00386(18) 0.0793(16) Uani 1 1 d . . . C115 C 1.1074(7) 0.7645(5) 0.02282(19) 0.0855(17) Uani 1 1 d . . . H115 H 1.0845 0.6985 0.0094 0.103 Uiso 1 1 calc R . . C116 C 1.0914(6) 0.7775(4) 0.06724(18) 0.0707(13) Uani 1 1 d . . . H116 H 1.0613 0.7199 0.0845 0.085 Uiso 1 1 calc R . . C117 C 1.1776(8) 0.8287(8) -0.0546(2) 0.120(3) Uani 1 1 d . . . H11A H 1.2105 0.8941 -0.0681 0.181 Uiso 1 1 calc R . . H11B H 1.1018 0.8115 -0.0686 0.181 Uiso 1 1 calc R . . H11C H 1.2324 0.7684 -0.0589 0.181 Uiso 1 1 calc R . . C211 C 0.6036(5) 0.9877(5) 0.37767(15) 0.0676(13) Uani 1 1 d . . . C212 C 0.5876(7) 0.8911(6) 0.4023(2) 0.096(2) Uani 1 1 d . . . H212 H 0.5685 0.8254 0.3878 0.115 Uiso 1 1 calc R . . C213 C 0.6006(8) 0.8941(7) 0.4491(2) 0.108(2) Uani 1 1 d . . . H213 H 0.5885 0.8303 0.4659 0.13 Uiso 1 1 calc R . . C214 C 0.6311(5) 0.9903(7) 0.47044(18) 0.0842(17) Uani 1 1 d . . . C215 C 0.6503(8) 1.0818(7) 0.4455(2) 0.106(2) Uani 1 1 d . . . H215 H 0.6721 1.1469 0.4599 0.128 Uiso 1 1 calc R . . C216 C 0.6386(8) 1.0815(6) 0.3997(2) 0.101(2) Uani 1 1 d . . . H216 H 0.6544 1.1454 0.3834 0.122 Uiso 1 1 calc R . . C217 C 0.6484(7) 0.9900(8) 0.5212(2) 0.119(3) Uani 1 1 d . . . H21A H 0.6735 1.0619 0.5309 0.178 Uiso 1 1 calc R . . H21B H 0.7089 0.9368 0.5291 0.178 Uiso 1 1 calc R . . H21C H 0.5738 0.9711 0.5355 0.178 Uiso 1 1 calc R . . C310 C 0.5960(4) 1.0566(4) 0.15776(15) 0.0605(11) Uani 1 1 d . . . C311 C 0.7195(4) 1.1660(4) 0.21519(13) 0.0490(9) Uani 1 1 d . . . H311 H 0.6597 1.1379 0.2365 0.059 Uiso 1 1 calc R . . C312 C 0.7478(5) 1.2839(4) 0.22880(16) 0.0590(11) Uani 1 1 d . . . H31A H 0.7796 1.2847 0.2588 0.088 Uiso 1 1 calc R . . H31B H 0.6755 1.3272 0.2277 0.088 Uiso 1 1 calc R . . H31C H 0.8062 1.3143 0.2085 0.088 Uiso 1 1 calc R . . N12 N 0.8180(3) 0.8510(3) 0.22306(11) 0.0510(8) Uani 1 1 d . . . N6 N 0.8335(3) 1.0908(3) 0.21922(10) 0.0415(7) Uani 1 1 d . . . H6 H 0.8095 1.0204 0.2136 0.05 Uiso 1 1 calc R . . N9 N 0.9503(3) 0.9346(3) 0.14945(11) 0.0522(8) Uani 1 1 d . . . N3 N 0.7277(3) 0.9771(3) 0.29801(11) 0.0537(8) Uani 1 1 d . . . O10 O 1.1612(3) 0.9887(3) 0.16023(12) 0.0700(9) Uani 1 1 d . . . O11 O 1.1008(4) 0.7933(3) 0.16623(11) 0.0732(10) Uani 1 1 d . . . O20 O 0.5332(4) 0.8863(4) 0.30541(13) 0.0981(14) Uani 1 1 d . . . O21 O 0.5429(4) 1.0888(4) 0.30561(13) 0.0928(13) Uani 1 1 d . . . S1 S 1.09172(11) 0.89810(9) 0.14477(3) 0.0533(3) Uani 1 1 d . . . S2 S 0.59028(12) 0.98493(13) 0.31925(4) 0.0710(4) Uani 1 1 d . . . S9 S 0.9187(3) 0.4529(2) 0.10865(8) 0.0734(5) Uiso 0.5 1 d PD . . O91 O 0.9739(11) 0.5589(6) 0.1100(4) 0.1207(13) Uiso 0.5 1 d PD . . O92 O 0.9495(5) 0.3813(4) 0.14479(16) 0.1207(13) Uiso 1 1 d D . . O93 O 0.7931(5) 0.4623(10) 0.0997(4) 0.1207(13) Uiso 0.5 1 d PD . . C91 C 1.0069(11) 0.3848(13) 0.0669(4) 0.129(4) Uiso 0.5 1 d PD . . F91 F 1.1218(12) 0.3726(14) 0.0765(5) 0.187(2) Uiso 0.5 1 d PD . . F92 F 0.9443(14) 0.3181(14) 0.0411(5) 0.187(2) Uiso 0.5 1 d PD . . F93 F 0.9982(15) 0.4394(14) 0.0289(5) 0.187(2) Uiso 0.5 1 d PD . . S92 S 0.9581(3) 0.4359(3) 0.10249(8) 0.0734(5) Uiso 0.5 1 d PD . . F923 F 1.0790(17) 0.3684(13) 0.0324(5) 0.187(2) Uiso 0.5 1 d PD . . O921 O 1.0407(10) 0.5257(8) 0.1037(4) 0.1207(13) Uiso 0.5 1 d PD . . O923 O 0.8410(6) 0.4408(10) 0.0830(4) 0.1207(13) Uiso 0.5 1 d PD . . F921 F 1.1235(14) 0.2836(14) 0.0920(5) 0.187(2) Uiso 0.5 1 d PD . . C92 C 1.0346(13) 0.3327(12) 0.0707(5) 0.129(4) Uiso 0.5 1 d PD . . F922 F 0.9592(14) 0.2503(13) 0.0649(5) 0.187(2) Uiso 0.5 1 d PD . . 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 C11 0.053(2) 0.052(2) 0.055(2) -0.0080(19) -0.009(2) 0.0013(19) C401 0.087(4) 0.048(3) 0.087(4) -0.017(3) -0.013(3) 0.000(2) C402 0.105(5) 0.043(3) 0.105(5) -0.002(3) -0.002(4) -0.019(3) C403 0.079(4) 0.057(3) 0.092(4) 0.016(3) -0.011(3) -0.017(3) C1 0.055(2) 0.052(2) 0.058(3) 0.009(2) -0.005(2) -0.004(2) C10 0.065(3) 0.067(3) 0.050(2) -0.011(2) -0.003(2) -0.005(2) C8 0.058(2) 0.065(2) 0.0367(18) 0.0024(17) 0.0038(18) 0.013(2) C7 0.052(2) 0.049(2) 0.047(2) 0.0000(17) 0.0087(18) 0.0011(17) C2 0.070(3) 0.066(3) 0.043(2) 0.016(2) -0.003(2) -0.011(2) C4 0.062(2) 0.053(2) 0.0379(18) -0.0052(17) 0.0002(17) -0.0050(19) C5 0.050(2) 0.053(2) 0.0377(17) 0.0027(16) -0.0037(16) -0.0080(18) C31 0.048(2) 0.062(2) 0.045(2) -0.0013(19) 0.0016(17) 0.0095(19) C32 0.069(3) 0.082(3) 0.052(2) 0.008(2) -0.006(2) 0.018(3) C33 0.090(4) 0.114(5) 0.054(3) 0.018(3) -0.004(3) 0.038(4) C34 0.084(4) 0.129(5) 0.050(3) -0.013(3) -0.021(3) 0.032(4) C35 0.063(3) 0.102(4) 0.070(3) -0.025(3) -0.027(2) 0.019(3) C36 0.093(5) 0.139(7) 0.112(6) -0.048(5) -0.039(4) -0.010(5) C37 0.105(6) 0.115(6) 0.174(9) -0.063(7) -0.029(6) -0.026(5) C38 0.083(4) 0.105(5) 0.135(6) -0.033(5) -0.004(4) -0.024(4) C39 0.052(3) 0.086(3) 0.080(3) -0.010(3) -0.009(2) -0.012(2) C111 0.053(2) 0.062(3) 0.047(2) -0.0032(19) 0.0057(18) 0.0058(19) C112 0.066(3) 0.067(3) 0.069(3) 0.000(2) 0.013(2) -0.006(2) C113 0.081(4) 0.100(4) 0.062(3) 0.016(3) 0.021(3) -0.021(3) C114 0.087(4) 0.100(4) 0.051(3) -0.005(3) 0.021(3) -0.008(3) C115 0.114(5) 0.077(3) 0.066(3) -0.022(3) 0.021(3) -0.004(3) C116 0.087(3) 0.059(3) 0.066(3) -0.007(2) 0.023(3) -0.001(3) C117 0.130(6) 0.172(8) 0.060(3) -0.020(4) 0.036(4) -0.027(6) C211 0.063(3) 0.094(4) 0.046(2) 0.014(2) 0.011(2) -0.010(3) C212 0.105(5) 0.114(5) 0.068(3) 0.017(3) 0.007(3) -0.040(4) C213 0.127(6) 0.136(6) 0.063(3) 0.025(4) 0.011(4) -0.031(5) C214 0.072(3) 0.129(5) 0.052(3) -0.008(3) 0.012(2) 0.001(4) C215 0.144(6) 0.118(5) 0.057(3) -0.011(4) 0.023(4) 0.002(5) C216 0.163(7) 0.081(4) 0.060(3) -0.002(3) 0.037(4) -0.007(4) C217 0.093(4) 0.202(9) 0.060(3) 0.014(5) 0.002(3) 0.018(6) C310 0.044(2) 0.078(3) 0.059(2) -0.014(2) -0.009(2) 0.007(2) C311 0.048(2) 0.058(2) 0.041(2) -0.0008(18) -0.0002(16) 0.0070(19) C312 0.069(3) 0.054(2) 0.054(3) -0.012(2) -0.007(2) 0.009(2) N12 0.056(2) 0.0508(19) 0.0465(18) -0.0006(15) -0.0017(16) -0.0053(16) N6 0.0470(16) 0.0393(16) 0.0382(15) -0.0025(13) -0.0010(13) 0.0002(14) N9 0.0545(19) 0.060(2) 0.0422(16) -0.0042(15) -0.0020(15) 0.0056(16) N3 0.058(2) 0.064(2) 0.0391(16) 0.0015(16) 0.0022(15) -0.0119(18) O10 0.0563(17) 0.084(2) 0.070(2) -0.0176(18) -0.0089(15) 0.0016(17) O11 0.097(3) 0.072(2) 0.0506(16) 0.0134(15) -0.0053(18) 0.030(2) O20 0.084(3) 0.144(4) 0.067(2) 0.002(3) -0.001(2) -0.043(3) O21 0.072(2) 0.142(4) 0.065(2) 0.026(2) 0.0046(18) 0.030(3) S1 0.0599(6) 0.0582(6) 0.0419(5) -0.0018(4) -0.0034(5) 0.0118(5) S2 0.0589(6) 0.1045(10) 0.0496(6) 0.0067(6) 0.0046(5) -0.0105(7) #----------------------------------------------------------------------------# # 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 C11 N12 1.339(5) . ? C11 C401 1.375(7) . ? C11 C10 1.510(7) . ? C401 C402 1.346(8) . ? C402 C403 1.380(8) . ? C403 C1 1.371(7) . ? C1 N12 1.342(6) . ? C1 C2 1.500(7) . ? C10 N9 1.465(6) . ? C8 N9 1.465(6) . ? C8 C7 1.520(6) . ? C7 N6 1.501(5) . ? C2 N3 1.478(6) . ? C4 N3 1.459(5) . ? C4 C5 1.511(6) . ? C5 N6 1.514(5) . ? C31 C32 1.366(7) . ? C31 C310 1.437(7) . ? C31 C311 1.523(6) . ? C32 C33 1.409(8) . ? C33 C34 1.348(10) . ? C34 C35 1.384(9) . ? C35 C36 1.413(11) . ? C35 C310 1.431(6) . ? C36 C37 1.340(13) . ? C37 C38 1.443(13) . ? C38 C39 1.369(8) . ? C39 C310 1.395(8) . ? C111 C116 1.395(7) . ? C111 C112 1.393(7) . ? C111 S1 1.755(4) . ? C112 C113 1.368(7) . ? C113 C114 1.339(8) . ? C114 C115 1.407(8) . ? C114 C117 1.544(8) . ? C115 C116 1.343(7) . ? C211 C216 1.370(9) . ? C211 C212 1.393(8) . ? C211 S2 1.745(5) . ? C212 C213 1.401(8) . ? C213 C214 1.371(10) . ? C214 C215 1.353(10) . ? C214 C217 1.521(8) . ? C215 C216 1.369(8) . ? C311 C312 1.519(6) . ? C311 N6 1.565(5) . ? N9 S1 1.637(4) . ? N3 S2 1.654(4) . ? O10 S1 1.419(4) . ? O11 S1 1.426(4) . ? O20 S2 1.415(5) . ? O21 S2 1.424(5) . ? S9 O92 1.424(4) . ? S9 O93 1.424(4) . ? S9 O91 1.424(4) . ? S9 C91 1.783(13) . ? O92 S92 1.425(4) . ? C91 F93 1.315(7) . ? C91 F92 1.315(7) . ? C91 F91 1.315(7) . ? F91 F923 1.40(2) . ? F91 S92 2.118(15) . ? F92 F93 1.63(2) . ? F92 F923 1.64(2) . ? S92 O921 1.424(4) . ? S92 O923 1.425(4) . ? S92 C92 1.783(13) . ? F923 C92 1.315(7) . ? F921 C92 1.315(7) . ? C92 F922 1.315(7) . ? 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 N12 C11 C401 122.0(5) . . ? N12 C11 C10 116.5(4) . . ? C401 C11 C10 121.5(4) . . ? C402 C401 C11 119.5(5) . . ? C401 C402 C403 119.8(5) . . ? C1 C403 C402 118.0(5) . . ? N12 C1 C403 122.8(5) . . ? N12 C1 C2 116.3(4) . . ? C403 C1 C2 120.9(4) . . ? N9 C10 C11 114.3(4) . . ? N9 C8 C7 113.0(3) . . ? N6 C7 C8 114.7(3) . . ? N3 C2 C1 112.6(4) . . ? N3 C4 C5 112.2(3) . . ? C4 C5 N6 115.3(3) . . ? C32 C31 C310 120.3(4) . . ? C32 C31 C311 119.8(4) . . ? C310 C31 C311 119.9(4) . . ? C31 C32 C33 121.0(6) . . ? C34 C33 C32 120.1(6) . . ? C33 C34 C35 121.1(5) . . ? C34 C35 C36 121.9(6) . . ? C34 C35 C310 120.9(5) . . ? C36 C35 C310 117.2(7) . . ? C37 C36 C35 122.3(7) . . ? C36 C37 C38 121.3(7) . . ? C39 C38 C37 116.7(8) . . ? C38 C39 C310 123.4(6) . . ? C116 C111 C112 119.4(4) . . ? C116 C111 S1 119.8(4) . . ? C112 C111 S1 120.7(4) . . ? C113 C112 C111 118.4(5) . . ? C114 C113 C112 123.4(5) . . ? C113 C114 C115 117.6(5) . . ? C113 C114 C117 122.7(6) . . ? C115 C114 C117 119.8(6) . . ? C116 C115 C114 121.5(5) . . ? C115 C116 C111 119.6(5) . . ? C216 C211 C212 118.9(5) . . ? C216 C211 S2 121.1(4) . . ? C212 C211 S2 119.8(5) . . ? C211 C212 C213 119.2(7) . . ? C214 C213 C212 120.5(7) . . ? C215 C214 C213 118.9(5) . . ? C215 C214 C217 121.8(7) . . ? C213 C214 C217 119.2(7) . . ? C214 C215 C216 122.0(7) . . ? C211 C216 C215 120.3(6) . . ? C39 C310 C35 119.1(5) . . ? C39 C310 C31 124.3(4) . . ? C35 C310 C31 116.6(5) . . ? C312 C311 C31 115.2(4) . . ? C312 C311 N6 111.2(3) . . ? C31 C311 N6 108.5(3) . . ? C11 N12 C1 117.8(4) . . ? C7 N6 C5 109.5(3) . . ? C7 N6 C311 112.1(3) . . ? C5 N6 C311 113.1(3) . . ? C10 N9 C8 120.7(4) . . ? C10 N9 S1 118.0(3) . . ? C8 N9 S1 116.8(3) . . ? C4 N3 C2 117.1(3) . . ? C4 N3 S2 115.2(3) . . ? C2 N3 S2 115.5(3) . . ? O10 S1 O11 120.4(2) . . ? O10 S1 N9 106.5(2) . . ? O11 S1 N9 105.7(2) . . ? O10 S1 C111 109.0(2) . . ? O11 S1 C111 107.4(2) . . ? N9 S1 C111 107.0(2) . . ? O20 S2 O21 120.0(3) . . ? O20 S2 N3 104.7(2) . . ? O21 S2 N3 106.4(2) . . ? O20 S2 C211 110.1(3) . . ? O21 S2 C211 107.4(3) . . ? N3 S2 C211 107.7(2) . . ? O92 S9 O93 115.2(6) . . ? O92 S9 O91 115.2(6) . . ? O93 S9 O91 110.8(8) . . ? O92 S9 C91 96.4(5) . . ? O93 S9 C91 116.3(6) . . ? O91 S9 C91 101.7(8) . . ? S9 O92 S92 20.94(18) . . ? F93 C91 F92 76.5(12) . . ? F93 C91 F91 108.3(15) . . ? F92 C91 F91 124.7(17) . . ? F93 C91 S9 109.0(12) . . ? F92 C91 S9 113.7(11) . . ? F91 C91 S9 115.7(12) . . ? C91 F91 F923 58.1(10) . . ? C91 F91 S92 37.5(8) . . ? F923 F91 S92 93.7(9) . . ? C91 F92 F93 51.7(6) . . ? C91 F92 F923 51.7(9) . . ? F93 F92 F923 44.9(8) . . ? C91 F93 F92 51.7(6) . . ? O921 S92 O923 124.4(8) . . ? O921 S92 O92 112.1(6) . . ? O923 S92 O92 108.5(6) . . ? O921 S92 C92 104.1(7) . . ? O923 S92 C92 104.3(7) . . ? O92 S92 C92 100.1(6) . . ? O921 S92 F91 74.6(7) . . ? O923 S92 F91 130.5(6) . . ? O92 S92 F91 102.2(6) . . ? C92 S92 F91 31.1(6) . . ? C92 F923 F91 47.5(10) . . ? C92 F923 F92 53.0(10) . . ? F91 F923 F92 100.1(10) . . ? F922 C92 F923 112.1(15) . . ? F922 C92 F921 101.3(14) . . ? F923 C92 F921 106.5(15) . . ? F922 C92 S92 107.4(11) . . ? F923 C92 S92 114.0(12) . . ? F921 C92 S92 114.9(12) . . ? # The following lines are used to test the character set of files sent by # network email or other means. They are not part of the CIF data set # abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789 # !@#$%^&*()_+{}:"~<>?|\-=[];'`,./ # END of CIF