# Electronic Supplementary Material (ESI) for Dalton Transactions # 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_5 #TrackingRef 'nikita_pub.cif' _audit_creation_method SHELXL-2012 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H36 I2 N2 S, C7 H8' _chemical_formula_sum 'C34 H44 I2 N2 S' _chemical_formula_weight 766.57 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0015 0.0009 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.0826 0.0763 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.8919 1.1868 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_H-M_alt 'C 2/c' _space_group_name_Hall '-C 2yc' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 37.684(3) _cell_length_b 11.414(2) _cell_length_c 16.103(2) _cell_angle_alpha 90 _cell_angle_beta 100.24(2) _cell_angle_gamma 90 _cell_volume 6816.0(16) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9909 _cell_measurement_theta_min 2.274 _cell_measurement_theta_max 23.204 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_density_diffrn 1.494 _exptl_crystal_F_000 3072 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.178 _exptl_crystal_size_mid 0.133 _exptl_crystal_size_min 0.063 _exptl_absorpt_coefficient_mu 1.027 _shelx_estimated_absorpt_T_min 0.838 _shelx_estimated_absorpt_T_max 0.938 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6452 _exptl_absorpt_correction_T_max 0.7449 _exptl_absorpt_process_details SADABS-2012/1 _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.56086 _diffrn_radiation_type AgK\a _diffrn_source 'INCOATEC Ag Microsource' _diffrn_measurement_device_type 'Smart APEX II Ultra' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 103802 _diffrn_reflns_av_unetI/netI 0.0302 _diffrn_reflns_av_R_equivalents 0.0635 _diffrn_reflns_limit_h_min -53 _diffrn_reflns_limit_h_max 53 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 0.867 _diffrn_reflns_theta_max 23.633 _diffrn_reflns_theta_full 19.665 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_point_group_measured_fraction_full 1.000 _reflns_number_total 10410 _reflns_number_gt 8687 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'APEX2 v2012.2' _computing_cell_refinement 'SAINT V7.68A' _computing_data_reduction 'SAINT V7.68A' _computing_structure_solution 'SHELXS-2012 (Sheldrick, 2012)' _computing_structure_refinement 'SHELXL-2012 (Sheldrick, 2012)' _computing_molecular_graphics 'Mercury Version 2.4' _computing_publication_material 'Mercury Version 2.4' _refine_special_details ; ? ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0282P)^2^+13.5461P] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 10410 _refine_ls_number_parameters 361 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0397 _refine_ls_R_factor_gt 0.0304 _refine_ls_wR_factor_ref 0.0687 _refine_ls_wR_factor_gt 0.0654 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.37994(2) 0.26699(2) 0.63182(2) 0.01668(4) Uani 1 1 d . . . . . S1 S 0.33808(2) 0.19297(5) 0.48781(3) 0.01718(10) Uani 1 1 d . . . . . N1 N 0.32869(4) 0.38688(15) 0.38595(10) 0.0138(3) Uani 1 1 d . . . . . C1 C 0.34858(5) 0.29220(17) 0.41670(12) 0.0132(3) Uani 1 1 d . . . . . I2 I 0.42604(2) 0.33270(2) 0.78604(2) 0.02897(5) Uani 1 1 d . . . . . N2 N 0.37729(4) 0.28929(14) 0.37623(10) 0.0124(3) Uani 1 1 d . . . . . C2 C 0.34518(5) 0.44320(18) 0.32625(13) 0.0159(4) Uani 1 1 d . . . . . H2 H 0.3369 0.5121 0.2957 0.019 Uiso 1 1 calc R U . . . C3 C 0.37507(5) 0.38166(17) 0.31985(12) 0.0150(4) Uani 1 1 d . . . . . H3 H 0.3916 0.3986 0.2833 0.018 Uiso 1 1 calc R U . . . C4 C 0.40219(5) 0.19188(17) 0.37831(12) 0.0138(4) Uani 1 1 d . . . . . C5 C 0.43677(5) 0.20072(18) 0.42687(12) 0.0142(4) Uani 1 1 d . . . . . C7 C 0.44892(6) 0.00855(19) 0.37444(14) 0.0217(4) Uani 1 1 d . . . . . H7 H 0.4652 -0.0547 0.3728 0.026 Uiso 1 1 calc R U . . . C6 C 0.46018(6) 0.10630(19) 0.42309(13) 0.0180(4) Uani 1 1 d . . . . . H6 H 0.4841 0.1093 0.4543 0.022 Uiso 1 1 calc R U . . . C8 C 0.41434(6) 0.00193(19) 0.32817(14) 0.0212(4) Uani 1 1 d . . . . . H8 H 0.4070 -0.0663 0.2958 0.025 Uiso 1 1 calc R U . . . C9 C 0.39012(6) 0.09427(18) 0.32845(13) 0.0174(4) Uani 1 1 d . . . . . C10 C 0.35267(6) 0.0882(2) 0.27370(14) 0.0219(4) Uani 1 1 d . . . . . H10 H 0.3392 0.1607 0.2842 0.026 Uiso 1 1 calc R U . . . C11 C 0.35544(6) 0.0854(2) 0.18001(15) 0.0254(5) Uani 1 1 d . . . . . H11A H 0.3313 0.0921 0.1458 0.038 Uiso 1 1 calc R U . . . H11B H 0.3664 0.0114 0.1670 0.038 Uiso 1 1 calc R U . . . H11C H 0.3704 0.1510 0.1673 0.038 Uiso 1 1 calc R U . . . C12 C 0.33134(7) -0.0176(3) 0.29698(17) 0.0340(6) Uani 1 1 d . . . . . H12A H 0.3070 -0.0164 0.2633 0.051 Uiso 1 1 calc R U . . . H12B H 0.3298 -0.0140 0.3571 0.051 Uiso 1 1 calc R U . . . H12C H 0.3436 -0.0900 0.2855 0.051 Uiso 1 1 calc R U . . . C13 C 0.44925(5) 0.30926(18) 0.47870(12) 0.0149(4) Uani 1 1 d . . . . . H13 H 0.4275 0.3482 0.4936 0.018 Uiso 1 1 calc R U . . . C14 C 0.46701(6) 0.3958(2) 0.42543(14) 0.0208(4) Uani 1 1 d . . . . . H14A H 0.4885 0.3596 0.4098 0.031 Uiso 1 1 calc R U . . . H14B H 0.4740 0.4670 0.4583 0.031 Uiso 1 1 calc R U . . . H14C H 0.4499 0.4160 0.3742 0.031 Uiso 1 1 calc R U . . . C15 C 0.47516(6) 0.2817(2) 0.56106(13) 0.0214(4) Uani 1 1 d . . . . . H15A H 0.4976 0.2495 0.5480 0.032 Uiso 1 1 calc R U . . . H15B H 0.4640 0.2243 0.5937 0.032 Uiso 1 1 calc R U . . . H15C H 0.4804 0.3537 0.5941 0.032 Uiso 1 1 calc R U . . . C16 C 0.29532(5) 0.42463(18) 0.41122(12) 0.0151(4) Uani 1 1 d . . . . . C17 C 0.26358(5) 0.36108(19) 0.38123(13) 0.0167(4) Uani 1 1 d . . . . . C18 C 0.23223(6) 0.3998(2) 0.40696(14) 0.0202(4) Uani 1 1 d . . . . . H18 H 0.2102 0.3592 0.3885 0.024 Uiso 1 1 calc R U . . . C19 C 0.23252(6) 0.4967(2) 0.45914(14) 0.0224(4) Uani 1 1 d . . . . . H19 H 0.2108 0.5211 0.4762 0.027 Uiso 1 1 calc R U . . . C20 C 0.26404(6) 0.5581(2) 0.48664(14) 0.0210(4) Uani 1 1 d . . . . . H20 H 0.2637 0.6251 0.5215 0.025 Uiso 1 1 calc R U . . . C21 C 0.29668(5) 0.52242(18) 0.46354(13) 0.0164(4) Uani 1 1 d . . . . . C22 C 0.33093(6) 0.59056(19) 0.49589(13) 0.0194(4) Uani 1 1 d . . . . . H22 H 0.3517 0.5459 0.4805 0.023 Uiso 1 1 calc R U . . . C23 C 0.32979(7) 0.7112(2) 0.45314(17) 0.0297(5) Uani 1 1 d . . . . . H23A H 0.3276 0.7009 0.3920 0.045 Uiso 1 1 calc R U . . . H23B H 0.3520 0.7541 0.4750 0.045 Uiso 1 1 calc R U . . . H23C H 0.3090 0.7554 0.4651 0.045 Uiso 1 1 calc R U . . . C24 C 0.33751(6) 0.6038(2) 0.59198(14) 0.0250(5) Uani 1 1 d . . . . . H24A H 0.3611 0.6405 0.6110 0.038 Uiso 1 1 calc R U . . . H24B H 0.3371 0.5264 0.6181 0.038 Uiso 1 1 calc R U . . . H24C H 0.3186 0.6529 0.6083 0.038 Uiso 1 1 calc R U . . . C25 C 0.26308(6) 0.25703(19) 0.32189(14) 0.0206(4) Uani 1 1 d . . . . . H25 H 0.2862 0.2133 0.3397 0.025 Uiso 1 1 calc R U . . . C26 C 0.26188(7) 0.2964(2) 0.23033(15) 0.0281(5) Uani 1 1 d . . . . . H26A H 0.2636 0.2277 0.1947 0.042 Uiso 1 1 calc R U . . . H26B H 0.2822 0.3492 0.2276 0.042 Uiso 1 1 calc R U . . . H26C H 0.2392 0.3376 0.2102 0.042 Uiso 1 1 calc R U . . . C27 C 0.23211(7) 0.1707(2) 0.32606(17) 0.0309(5) Uani 1 1 d . . . . . H27A H 0.2091 0.2078 0.3024 0.046 Uiso 1 1 calc R U . . . H27B H 0.2321 0.1490 0.3850 0.046 Uiso 1 1 calc R U . . . H27C H 0.2354 0.1003 0.2934 0.046 Uiso 1 1 calc R U . . . C28 C 0.44397(7) 0.8332(2) 0.61726(17) 0.0279(5) Uani 1 1 d . . . . . C29 C 0.43148(6) 0.7782(2) 0.54046(16) 0.0285(5) Uani 1 1 d . . . . . H29 H 0.4253 0.8244 0.4909 0.034 Uiso 1 1 calc R U . . . C30 C 0.42782(6) 0.6571(2) 0.53482(15) 0.0265(5) Uani 1 1 d . . . . . H30 H 0.4192 0.6212 0.4818 0.032 Uiso 1 1 calc R U . . . C31 C 0.43672(6) 0.5889(2) 0.60673(15) 0.0235(4) Uani 1 1 d . . . . . H31 H 0.4339 0.5062 0.6034 0.028 Uiso 1 1 calc R U . . . C32 C 0.44972(6) 0.6418(2) 0.68324(14) 0.0233(4) Uani 1 1 d . . . . . H32 H 0.4563 0.5950 0.7323 0.028 Uiso 1 1 calc R U . . . C33 C 0.45325(7) 0.7630(2) 0.68903(15) 0.0250(5) Uani 1 1 d . . . . . H33 H 0.4620 0.7983 0.7421 0.030 Uiso 1 1 calc R U . . . C34 C 0.44764(9) 0.9645(2) 0.6233(2) 0.0460(8) Uani 1 1 d . . . . . H34A H 0.4705 0.9883 0.6071 0.069 Uiso 1 1 calc R U . . . H34B H 0.4473 0.9894 0.6814 0.069 Uiso 1 1 calc R U . . . H34C H 0.4275 1.0012 0.5852 0.069 Uiso 1 1 calc R U . . . 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 I1 0.02287(7) 0.01302(6) 0.01545(6) 0.00269(5) 0.00699(5) 0.00084(5) S1 0.0185(2) 0.0170(2) 0.0166(2) 0.00314(18) 0.00475(18) -0.00361(18) N1 0.0124(7) 0.0144(8) 0.0147(7) 0.0009(6) 0.0033(6) 0.0005(6) C1 0.0123(8) 0.0132(9) 0.0138(8) -0.0015(7) 0.0016(7) -0.0013(7) I2 0.05064(11) 0.01503(7) 0.01816(7) -0.00065(5) -0.00229(6) -0.00296(6) N2 0.0121(7) 0.0119(8) 0.0133(7) -0.0003(6) 0.0025(6) -0.0007(6) C2 0.0174(9) 0.0149(9) 0.0160(9) 0.0030(7) 0.0047(7) 0.0009(7) C3 0.0162(9) 0.0151(9) 0.0140(9) 0.0005(7) 0.0038(7) -0.0009(7) C4 0.0144(9) 0.0110(9) 0.0172(9) 0.0005(7) 0.0056(7) 0.0013(7) C5 0.0147(9) 0.0150(9) 0.0140(8) 0.0018(7) 0.0055(7) 0.0005(7) C7 0.0277(11) 0.0142(10) 0.0246(11) 0.0006(8) 0.0086(9) 0.0059(8) C6 0.0168(9) 0.0194(10) 0.0183(9) 0.0016(8) 0.0039(7) 0.0046(8) C8 0.0270(11) 0.0122(9) 0.0253(11) -0.0035(8) 0.0068(9) -0.0005(8) C9 0.0181(10) 0.0151(9) 0.0199(10) -0.0010(8) 0.0053(8) -0.0025(7) C10 0.0175(10) 0.0207(11) 0.0270(11) -0.0090(9) 0.0029(8) -0.0032(8) C11 0.0250(11) 0.0223(11) 0.0271(11) -0.0025(9) -0.0003(9) -0.0028(9) C12 0.0311(13) 0.0405(15) 0.0319(13) -0.0111(11) 0.0094(10) -0.0181(11) C13 0.0131(9) 0.0165(9) 0.0148(9) -0.0003(7) 0.0018(7) 0.0000(7) C14 0.0214(10) 0.0210(11) 0.0201(10) 0.0016(8) 0.0038(8) -0.0051(8) C15 0.0224(10) 0.0243(11) 0.0162(9) -0.0003(8) -0.0006(8) 0.0012(8) C16 0.0131(9) 0.0179(10) 0.0152(9) 0.0021(7) 0.0052(7) 0.0028(7) C17 0.0160(9) 0.0177(10) 0.0162(9) 0.0026(7) 0.0024(7) 0.0010(7) C18 0.0133(9) 0.0268(11) 0.0208(10) 0.0038(8) 0.0039(7) 0.0007(8) C19 0.0170(10) 0.0291(12) 0.0227(10) 0.0017(9) 0.0077(8) 0.0049(8) C20 0.0208(10) 0.0219(11) 0.0213(10) -0.0004(8) 0.0064(8) 0.0061(8) C21 0.0169(9) 0.0162(9) 0.0164(9) 0.0014(7) 0.0039(7) 0.0024(7) C22 0.0186(10) 0.0200(10) 0.0199(10) -0.0044(8) 0.0042(8) 0.0003(8) C23 0.0289(12) 0.0233(12) 0.0360(13) 0.0031(10) 0.0034(10) -0.0025(10) C24 0.0252(11) 0.0280(12) 0.0214(10) -0.0063(9) 0.0030(9) 0.0022(9) C25 0.0138(9) 0.0202(10) 0.0267(11) -0.0071(8) 0.0008(8) -0.0008(8) C26 0.0303(12) 0.0334(13) 0.0216(11) -0.0050(10) 0.0076(9) -0.0019(10) C27 0.0270(12) 0.0281(13) 0.0369(14) -0.0005(10) 0.0038(10) -0.0084(10) C28 0.0302(12) 0.0225(11) 0.0370(13) 0.0048(10) 0.0223(11) 0.0025(9) C29 0.0264(12) 0.0347(14) 0.0273(12) 0.0122(10) 0.0125(9) 0.0049(10) C30 0.0232(11) 0.0368(14) 0.0203(10) -0.0022(9) 0.0057(9) -0.0041(10) C31 0.0229(11) 0.0222(11) 0.0275(11) -0.0022(9) 0.0102(9) -0.0026(9) C32 0.0253(11) 0.0266(12) 0.0202(10) 0.0047(9) 0.0100(8) 0.0016(9) C33 0.0292(12) 0.0268(12) 0.0220(11) -0.0040(9) 0.0126(9) -0.0020(9) C34 0.062(2) 0.0224(13) 0.064(2) 0.0013(13) 0.0414(17) 0.0000(13) _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 I1 S1 2.6981(7) . ? I1 I2 2.8662(6) . ? S1 C1 1.706(2) . ? N1 C1 1.358(3) . ? N1 C2 1.391(2) . ? N1 C16 1.454(2) . ? C1 N2 1.359(2) . ? N2 C3 1.384(2) . ? N2 C4 1.452(2) . ? C2 C3 1.347(3) . ? C4 C5 1.399(3) . ? C4 C9 1.401(3) . ? C5 C6 1.401(3) . ? C5 C13 1.521(3) . ? C7 C8 1.383(3) . ? C7 C6 1.386(3) . ? C8 C9 1.395(3) . ? C9 C10 1.527(3) . ? C10 C11 1.531(3) . ? C10 C12 1.533(3) . ? C13 C15 1.533(3) . ? C13 C14 1.537(3) . ? C16 C21 1.394(3) . ? C16 C17 1.409(3) . ? C17 C18 1.392(3) . ? C17 C25 1.522(3) . ? C18 C19 1.388(3) . ? C19 C20 1.383(3) . ? C20 C21 1.407(3) . ? C21 C22 1.518(3) . ? C22 C24 1.530(3) . ? C22 C23 1.536(3) . ? C25 C26 1.535(3) . ? C25 C27 1.538(3) . ? C28 C29 1.392(4) . ? C28 C33 1.399(3) . ? C28 C34 1.507(4) . ? C29 C30 1.391(4) . ? C30 C31 1.386(3) . ? C31 C32 1.381(3) . ? C32 C33 1.391(3) . ? 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 S1 I1 I2 176.805(13) . . ? C1 S1 I1 101.47(7) . . ? C1 N1 C2 109.53(16) . . ? C1 N1 C16 125.65(17) . . ? C2 N1 C16 124.83(17) . . ? N1 C1 N2 106.24(17) . . ? N1 C1 S1 126.45(15) . . ? N2 C1 S1 127.23(15) . . ? C1 N2 C3 109.61(16) . . ? C1 N2 C4 125.05(17) . . ? C3 N2 C4 124.19(16) . . ? C3 C2 N1 107.11(17) . . ? C2 C3 N2 107.51(17) . . ? C5 C4 C9 123.57(18) . . ? C5 C4 N2 119.46(17) . . ? C9 C4 N2 116.94(17) . . ? C4 C5 C6 116.83(19) . . ? C4 C5 C13 122.14(18) . . ? C6 C5 C13 120.98(18) . . ? C8 C7 C6 120.9(2) . . ? C7 C6 C5 120.8(2) . . ? C7 C8 C9 120.8(2) . . ? C8 C9 C4 117.17(19) . . ? C8 C9 C10 120.12(19) . . ? C4 C9 C10 122.68(19) . . ? C9 C10 C11 110.61(18) . . ? C9 C10 C12 111.4(2) . . ? C11 C10 C12 110.82(19) . . ? C5 C13 C15 113.26(17) . . ? C5 C13 C14 109.88(16) . . ? C15 C13 C14 109.94(17) . . ? C21 C16 C17 123.87(18) . . ? C21 C16 N1 117.75(18) . . ? C17 C16 N1 118.38(18) . . ? C18 C17 C16 116.64(19) . . ? C18 C17 C25 121.21(19) . . ? C16 C17 C25 122.13(18) . . ? C19 C18 C17 121.2(2) . . ? C20 C19 C18 120.8(2) . . ? C19 C20 C21 120.7(2) . . ? C16 C21 C20 116.85(19) . . ? C16 C21 C22 123.75(18) . . ? C20 C21 C22 119.41(19) . . ? C21 C22 C24 111.87(18) . . ? C21 C22 C23 110.55(18) . . ? C24 C22 C23 110.57(19) . . ? C17 C25 C26 111.68(19) . . ? C17 C25 C27 113.42(19) . . ? C26 C25 C27 109.68(19) . . ? C29 C28 C33 118.1(2) . . ? C29 C28 C34 121.2(3) . . ? C33 C28 C34 120.7(3) . . ? C30 C29 C28 121.3(2) . . ? C31 C30 C29 119.8(2) . . ? C32 C31 C30 119.6(2) . . ? C31 C32 C33 120.6(2) . . ? C32 C33 C28 120.5(2) . . ? _refine_diff_density_max 1.439 _refine_diff_density_min -0.997 _refine_diff_density_rms 0.097 _database_code_depnum_ccdc_archive 'CCDC 933418' ####################################################################### # # 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_6 #TrackingRef 'nikita_pub.cif' _audit_creation_method SHELXL-2012 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H35 I2 N S' _chemical_formula_sum 'C23 H35 I2 N S' _chemical_formula_weight 611.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0015 0.0009 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.0826 0.0763 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.8919 1.1868 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.520(2) _cell_length_b 11.141(2) _cell_length_c 12.138(2) _cell_angle_alpha 91.69(2) _cell_angle_beta 100.62(2) _cell_angle_gamma 103.70(2) _cell_volume 1225.7(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9946 _cell_measurement_theta_min 2.291 _cell_measurement_theta_max 26.238 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_density_diffrn 1.657 _exptl_crystal_F_000 604 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.118 _exptl_crystal_size_mid 0.102 _exptl_crystal_size_min 0.088 _exptl_absorpt_coefficient_mu 1.412 _shelx_estimated_absorpt_T_min 0.851 _shelx_estimated_absorpt_T_max 0.886 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.8996 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details SADABS-2012/1 _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.56086 _diffrn_radiation_type AgK\a _diffrn_source 'INCOATEC Ag Microsource' _diffrn_measurement_device_type 'Bruker Smart APEX II Quazar' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 50088 _diffrn_reflns_av_unetI/netI 0.0356 _diffrn_reflns_av_R_equivalents 0.0454 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.351 _diffrn_reflns_theta_max 25.679 _diffrn_reflns_theta_full 19.665 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_point_group_measured_fraction_full 1.000 _reflns_number_total 9450 _reflns_number_gt 7716 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'APEX2 v2012.2' _computing_cell_refinement 'SAINT V7.68A' _computing_data_reduction 'SAINT V7.68A' _computing_structure_solution 'SHELXS-2012 (Sheldrick, 2012)' _computing_structure_refinement 'SHELXL-2012 (Sheldrick, 2012)' _computing_molecular_graphics 'Mercury Version 2.4' _computing_publication_material 'Mercury Version 2.4' _refine_special_details ; ? ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0204P)^2^+0.1201P] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 9450 _refine_ls_number_parameters 250 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0357 _refine_ls_R_factor_gt 0.0255 _refine_ls_wR_factor_ref 0.0552 _refine_ls_wR_factor_gt 0.0527 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.29494(2) 1.17989(2) 0.19133(2) 0.01281(3) Uani 1 1 d . . . . . S1 S 0.17207(5) 0.97637(4) 0.30431(3) 0.01530(8) Uani 1 1 d . . . . . N1 N 0.07409(15) 0.73281(12) 0.28562(11) 0.0105(2) Uani 1 1 d . . . . . C1 C 0.13089(17) 0.83299(14) 0.23726(13) 0.0105(3) Uani 1 1 d . . . . . I2 I 0.39776(2) 1.39808(2) 0.08655(2) 0.02120(3) Uani 1 1 d . . . . . C2 C 0.15702(17) 0.79970(14) 0.12177(13) 0.0107(3) Uani 1 1 d . . . . . C3 C 0.0786(2) 0.65902(15) 0.10146(14) 0.0156(3) Uani 1 1 d . . . . . H3A H -0.0145 0.6464 0.0455 0.019 Uiso 1 1 calc R U . . . H3B H 0.1428 0.6129 0.0723 0.019 Uiso 1 1 calc R U . . . C4 C 0.04625(19) 0.61189(14) 0.21428(13) 0.0127(3) Uani 1 1 d . . . . . C5 C -0.1125(2) 0.53723(16) 0.20480(15) 0.0186(3) Uani 1 1 d . . . . . H5A H -0.1314 0.5195 0.2800 0.028 Uiso 1 1 calc R U . . . H5B H -0.1281 0.4592 0.1596 0.028 Uiso 1 1 calc R U . . . H5C H -0.1800 0.5850 0.1687 0.028 Uiso 1 1 calc R U . . . C6 C 0.1501(2) 0.53380(15) 0.26501(15) 0.0188(3) Uani 1 1 d . . . . . H6A H 0.1341 0.5145 0.3407 0.028 Uiso 1 1 calc R U . . . H6B H 0.2525 0.5801 0.2693 0.028 Uiso 1 1 calc R U . . . H6C H 0.1304 0.4566 0.2176 0.028 Uiso 1 1 calc R U . . . C7 C 0.08808(18) 0.87316(15) 0.03074(13) 0.0131(3) Uani 1 1 d . . . . . H7A H -0.0205 0.8501 0.0231 0.016 Uiso 1 1 calc R U . . . H7B H 0.1235 0.9628 0.0540 0.016 Uiso 1 1 calc R U . . . C9 C 0.2943(2) 0.87694(18) -0.07368(15) 0.0233(4) Uani 1 1 d . . . . . H9A H 0.3170 0.8569 -0.1475 0.028 Uiso 1 1 calc R U . . . H9B H 0.3370 0.9665 -0.0531 0.028 Uiso 1 1 calc R U . . . C11 C 0.32527(18) 0.82639(16) 0.12877(14) 0.0159(3) Uani 1 1 d . . . . . H11A H 0.3710 0.9138 0.1569 0.019 Uiso 1 1 calc R U . . . H11B H 0.3667 0.7731 0.1831 0.019 Uiso 1 1 calc R U . . . C10 C 0.3641(2) 0.80263(18) 0.01459(16) 0.0223(4) Uani 1 1 d . . . . . H10A H 0.4725 0.8261 0.0217 0.027 Uiso 1 1 calc R U . . . H10B H 0.3286 0.7132 -0.0097 0.027 Uiso 1 1 calc R U . . . C8 C 0.1275(2) 0.84796(17) -0.08307(14) 0.0188(3) Uani 1 1 d . . . . . H8A H 0.0838 0.7599 -0.1100 0.023 Uiso 1 1 calc R U . . . H8B H 0.0854 0.8996 -0.1387 0.023 Uiso 1 1 calc R U . . . C16 C -0.1309(2) 0.75996(15) 0.51503(14) 0.0162(3) Uani 1 1 d . . . . . H16 H -0.2242 0.7707 0.5242 0.019 Uiso 1 1 calc R U . . . C17 C -0.09858(18) 0.75763(14) 0.40726(13) 0.0126(3) Uani 1 1 d . . . . . C18 C -0.21118(19) 0.78197(16) 0.30935(15) 0.0166(3) Uani 1 1 d . . . . . H18 H -0.1729 0.7743 0.2388 0.020 Uiso 1 1 calc R U . . . C19 C -0.2305(2) 0.91428(17) 0.32379(18) 0.0253(4) Uani 1 1 d . . . . . H19A H -0.1347 0.9738 0.3308 0.038 Uiso 1 1 calc R U . . . H19B H -0.2702 0.9233 0.3917 0.038 Uiso 1 1 calc R U . . . H19C H -0.2988 0.9301 0.2581 0.038 Uiso 1 1 calc R U . . . C20 C -0.3609(2) 0.68713(18) 0.29675(17) 0.0233(4) Uani 1 1 d . . . . . H20A H -0.4073 0.7012 0.3600 0.035 Uiso 1 1 calc R U . . . H20B H -0.3458 0.6031 0.2960 0.035 Uiso 1 1 calc R U . . . H20C H -0.4250 0.6967 0.2262 0.035 Uiso 1 1 calc R U . . . C21 C 0.30447(18) 0.72727(15) 0.48638(15) 0.0155(3) Uani 1 1 d . . . . . H21 H 0.3111 0.7179 0.4054 0.019 Uiso 1 1 calc R U . . . C22 C 0.4104(2) 0.85037(17) 0.53819(16) 0.0221(4) Uani 1 1 d . . . . . H22A H 0.4069 0.8608 0.6180 0.033 Uiso 1 1 calc R U . . . H22B H 0.3810 0.9189 0.4991 0.033 Uiso 1 1 calc R U . . . H22C H 0.5110 0.8500 0.5305 0.033 Uiso 1 1 calc R U . . . C23 C 0.3513(2) 0.61811(17) 0.54514(16) 0.0225(4) Uani 1 1 d . . . . . H23A H 0.3569 0.6305 0.6263 0.034 Uiso 1 1 calc R U . . . H23B H 0.4481 0.6139 0.5309 0.034 Uiso 1 1 calc R U . . . H23C H 0.2786 0.5406 0.5156 0.034 Uiso 1 1 calc R U . . . C15 C -0.0289(2) 0.74691(15) 0.60872(14) 0.0174(3) Uani 1 1 d . . . . . H15 H -0.0534 0.7476 0.6811 0.021 Uiso 1 1 calc R U . . . C14 C 0.1075(2) 0.73305(15) 0.59698(14) 0.0164(3) Uani 1 1 d . . . . . H14 H 0.1767 0.7257 0.6621 0.020 Uiso 1 1 calc R U . . . C13 C 0.14696(18) 0.72956(14) 0.49183(14) 0.0128(3) Uani 1 1 d . . . . . C12 C 0.03964(18) 0.73880(14) 0.39700(13) 0.0102(3) 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 I1 0.01215(5) 0.01360(5) 0.01201(5) 0.00092(4) 0.00196(4) 0.00216(4) S1 0.0243(2) 0.00920(17) 0.01158(18) 0.00083(14) 0.00583(16) 0.00081(16) N1 0.0128(6) 0.0098(6) 0.0094(6) 0.0015(5) 0.0025(5) 0.0034(5) C1 0.0111(7) 0.0111(7) 0.0098(7) 0.0021(5) 0.0016(5) 0.0042(6) I2 0.02521(7) 0.01474(6) 0.02775(7) 0.00696(5) 0.01485(5) 0.00488(5) C2 0.0122(7) 0.0106(7) 0.0097(7) 0.0012(5) 0.0025(5) 0.0030(6) C3 0.0233(9) 0.0113(7) 0.0116(7) -0.0005(6) 0.0042(6) 0.0029(6) C4 0.0176(8) 0.0084(7) 0.0122(7) -0.0002(5) 0.0037(6) 0.0026(6) C5 0.0204(9) 0.0129(7) 0.0204(9) -0.0029(6) 0.0053(7) -0.0005(7) C6 0.0264(10) 0.0128(7) 0.0193(8) 0.0014(6) 0.0044(7) 0.0092(7) C7 0.0141(7) 0.0148(7) 0.0100(7) 0.0016(6) 0.0003(6) 0.0041(6) C9 0.0257(10) 0.0271(10) 0.0161(8) 0.0003(7) 0.0109(7) -0.0007(8) C11 0.0126(8) 0.0196(8) 0.0165(8) 0.0009(6) 0.0025(6) 0.0063(6) C10 0.0175(9) 0.0263(9) 0.0245(9) -0.0032(8) 0.0101(7) 0.0046(7) C8 0.0253(9) 0.0202(8) 0.0091(7) 0.0011(6) 0.0027(6) 0.0025(7) C16 0.0183(8) 0.0136(7) 0.0180(8) 0.0003(6) 0.0079(6) 0.0029(6) C17 0.0149(8) 0.0091(7) 0.0134(7) 0.0007(6) 0.0030(6) 0.0025(6) C18 0.0160(8) 0.0184(8) 0.0184(8) 0.0037(6) 0.0048(6) 0.0084(7) C19 0.0278(10) 0.0208(9) 0.0333(11) 0.0086(8) 0.0100(8) 0.0138(8) C20 0.0159(9) 0.0256(9) 0.0290(10) 0.0043(8) 0.0026(7) 0.0075(7) C21 0.0133(8) 0.0156(7) 0.0169(8) 0.0041(6) 0.0010(6) 0.0036(6) C22 0.0169(8) 0.0189(8) 0.0257(9) 0.0053(7) -0.0024(7) -0.0001(7) C23 0.0224(9) 0.0194(9) 0.0262(10) 0.0076(7) 0.0008(7) 0.0084(7) C15 0.0262(9) 0.0134(7) 0.0126(7) 0.0009(6) 0.0080(7) 0.0013(7) C14 0.0218(9) 0.0139(7) 0.0115(7) 0.0013(6) 0.0000(6) 0.0028(7) C13 0.0155(8) 0.0086(7) 0.0131(7) 0.0017(5) 0.0027(6) 0.0010(6) C12 0.0134(7) 0.0084(6) 0.0086(6) 0.0013(5) 0.0036(5) 0.0011(6) _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 I1 S1 2.8121(7) . ? I1 I2 2.8282(6) . ? S1 C1 1.6961(16) . ? N1 C1 1.324(2) . ? N1 C12 1.452(2) . ? N1 C4 1.521(2) . ? C1 C2 1.519(2) . ? C2 C7 1.537(2) . ? C2 C11 1.544(2) . ? C2 C3 1.559(2) . ? C3 C4 1.538(2) . ? C4 C5 1.524(2) . ? C4 C6 1.526(2) . ? C7 C8 1.532(2) . ? C9 C10 1.525(3) . ? C9 C8 1.526(3) . ? C11 C10 1.530(2) . ? C16 C15 1.388(2) . ? C16 C17 1.399(2) . ? C17 C12 1.407(2) . ? C17 C18 1.524(2) . ? C18 C19 1.537(2) . ? C18 C20 1.539(3) . ? C21 C13 1.519(2) . ? C21 C22 1.534(2) . ? C21 C23 1.542(2) . ? C15 C14 1.376(3) . ? C14 C13 1.397(2) . ? C13 C12 1.415(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 S1 I1 I2 173.783(10) . . ? C1 S1 I1 118.08(6) . . ? C1 N1 C12 122.47(13) . . ? C1 N1 C4 114.45(13) . . ? C12 N1 C4 123.08(13) . . ? N1 C1 C2 111.34(13) . . ? N1 C1 S1 121.44(12) . . ? C2 C1 S1 127.18(12) . . ? C1 C2 C7 112.12(13) . . ? C1 C2 C11 107.76(13) . . ? C7 C2 C11 110.27(13) . . ? C1 C2 C3 102.66(13) . . ? C7 C2 C3 110.68(13) . . ? C11 C2 C3 113.13(14) . . ? C4 C3 C2 108.02(13) . . ? N1 C4 C5 110.55(13) . . ? N1 C4 C6 110.90(13) . . ? C5 C4 C6 108.89(14) . . ? N1 C4 C3 101.57(12) . . ? C5 C4 C3 112.63(14) . . ? C6 C4 C3 112.17(14) . . ? C8 C7 C2 111.62(14) . . ? C10 C9 C8 111.04(15) . . ? C10 C11 C2 112.02(14) . . ? C9 C10 C11 110.98(15) . . ? C9 C8 C7 110.95(14) . . ? C15 C16 C17 121.16(16) . . ? C16 C17 C12 117.61(15) . . ? C16 C17 C18 118.29(15) . . ? C12 C17 C18 124.02(14) . . ? C17 C18 C19 110.47(15) . . ? C17 C18 C20 111.74(14) . . ? C19 C18 C20 110.23(15) . . ? C13 C21 C22 109.97(14) . . ? C13 C21 C23 112.42(15) . . ? C22 C21 C23 110.15(14) . . ? C14 C15 C16 120.14(16) . . ? C15 C14 C13 121.72(16) . . ? C14 C13 C12 117.22(15) . . ? C14 C13 C21 118.75(15) . . ? C12 C13 C21 123.81(15) . . ? C17 C12 C13 122.04(15) . . ? C17 C12 N1 118.59(14) . . ? C13 C12 N1 119.34(14) . . ? _refine_diff_density_max 1.162 _refine_diff_density_min -0.947 _refine_diff_density_rms 0.109 _database_code_depnum_ccdc_archive 'CCDC 933419' ####################################################################### # # 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_7 #TrackingRef 'nikita_pub.cif' _audit_creation_method SHELXL-2013 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H31 I2 N Se' _chemical_formula_sum 'C20 H31 I2 N Se' _chemical_formula_weight 618.22 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0015 0.0009 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se 0.2367 1.4831 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.8919 1.1868 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.8690(10) _cell_length_b 9.876(2) _cell_length_c 11.9680(10) _cell_angle_alpha 92.040(10) _cell_angle_beta 100.33(2) _cell_angle_gamma 93.280(10) _cell_volume 1144.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9998 _cell_measurement_theta_min 2.177 _cell_measurement_theta_max 21.376 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.794 _exptl_crystal_F_000 596 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.128 _exptl_crystal_size_mid 0.061 _exptl_crystal_size_min 0.047 _exptl_absorpt_coefficient_mu 2.303 _shelx_estimated_absorpt_T_min 0.757 _shelx_estimated_absorpt_T_max 0.899 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8043 _exptl_absorpt_correction_T_max 0.8618 _exptl_absorpt_process_details 'SADABS-2012/1, Sheldrick, Goettingen' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.56086 _diffrn_radiation_type AgK\a _diffrn_source 'INCOATEC Ag Microsource' _diffrn_measurement_device_type 'Bruker Smart Apex II Quazar' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 33744 _diffrn_reflns_av_unetI/netI 0.0235 _diffrn_reflns_av_R_equivalents 0.0361 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.366 _diffrn_reflns_theta_max 21.395 _diffrn_reflns_theta_full 19.665 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_point_group_measured_fraction_full 1.000 _reflns_number_total 5274 _reflns_number_gt 4648 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'APEX2 v2012.2' _computing_cell_refinement 'SAINT V7.68A' _computing_data_reduction 'SAINT V7.68A' _computing_structure_solution 'SHELXS-2012 (Sheldrick, 2012)' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_molecular_graphics 'Mercury Version 2.4' _computing_publication_material 'Mercury Version 2.4' _refine_special_details ; ? ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0140P)^2^+0.6769P] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 5274 _refine_ls_number_parameters 225 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0247 _refine_ls_R_factor_gt 0.0194 _refine_ls_wR_factor_ref 0.0407 _refine_ls_wR_factor_gt 0.0390 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.12787(2) 0.25216(2) 0.81536(2) 0.01601(4) Uani 1 1 d . . . . . N1 N 0.30098(17) 0.17598(17) 1.24058(14) 0.0117(3) Uani 1 1 d . . . . . C1 C 0.2255(2) 0.1920(2) 1.14023(17) 0.0125(4) Uani 1 1 d . . . . . I2 I -0.00212(2) 0.35793(2) 0.60286(2) 0.02425(5) Uani 1 1 d . . . . . C2 C 0.0878(2) 0.2485(2) 1.15119(18) 0.0144(4) Uani 1 1 d . . . . . Se3 Se 0.29038(2) 0.14933(2) 1.00804(2) 0.01609(5) Uani 1 1 d . . . . . C4 C 0.2307(2) 0.2136(2) 1.34038(18) 0.0161(4) Uani 1 1 d . . . . . C5 C 0.4427(2) 0.1342(2) 1.25794(17) 0.0125(4) Uani 1 1 d . . . . . C6 C 0.4662(2) -0.0040(2) 1.26912(17) 0.0144(4) Uani 1 1 d . . . . . C7 C 0.6024(2) -0.0385(2) 1.29287(19) 0.0182(5) Uani 1 1 d . . . . . H7 H 0.6213 -0.1313 1.3003 0.022 Uiso 1 1 calc R U . . . C8 C 0.7115(2) 0.0588(2) 1.3060(2) 0.0210(5) Uani 1 1 d . . . . . H8 H 0.8037 0.0330 1.3259 0.025 Uiso 1 1 calc R U . . . C9 C 0.6859(2) 0.1933(2) 1.29012(18) 0.0178(5) Uani 1 1 d . . . . . H9 H 0.7614 0.2592 1.2979 0.021 Uiso 1 1 calc R U . . . C10 C 0.5515(2) 0.2347(2) 1.26286(17) 0.0142(4) Uani 1 1 d . . . . . C11 C 0.0930(2) 0.3995(2) 1.12093(19) 0.0214(5) Uani 1 1 d . . . . . H11A H 0.1032 0.4061 1.0413 0.032 Uiso 1 1 calc R U . . . H11B H 0.1718 0.4488 1.1702 0.032 Uiso 1 1 calc R U . . . H11C H 0.0074 0.4392 1.1321 0.032 Uiso 1 1 calc R U . . . C12 C -0.0349(2) 0.1693(3) 1.07635(19) 0.0225(5) Uani 1 1 d . . . . . H12A H -0.0313 0.1826 0.9962 0.034 Uiso 1 1 calc R U . . . H12B H -0.1210 0.2021 1.0938 0.034 Uiso 1 1 calc R U . . . H12C H -0.0312 0.0725 1.0911 0.034 Uiso 1 1 calc R U . . . C13 C 0.2354(3) 0.1003(3) 1.4232(2) 0.0261(6) Uani 1 1 d . . . . . H13A H 0.1916 0.0164 1.3830 0.039 Uiso 1 1 calc R U . . . H13B H 0.1859 0.1251 1.4842 0.039 Uiso 1 1 calc R U . . . H13C H 0.3317 0.0863 1.4558 0.039 Uiso 1 1 calc R U . . . C14 C 0.3006(2) 0.3432(3) 1.40268(19) 0.0233(5) Uani 1 1 d . . . . . H14A H 0.2984 0.4163 1.3492 0.035 Uiso 1 1 calc R U . . . H14B H 0.3966 0.3279 1.4350 0.035 Uiso 1 1 calc R U . . . H14C H 0.2518 0.3689 1.4639 0.035 Uiso 1 1 calc R U . . . C16 C 0.3646(3) -0.2084(3) 1.3540(2) 0.0303(6) Uani 1 1 d . . . . . H16A H 0.2883 -0.2785 1.3411 0.045 Uiso 1 1 calc R U . . . H16B H 0.3600 -0.1524 1.4223 0.045 Uiso 1 1 calc R U . . . H16C H 0.4526 -0.2517 1.3643 0.045 Uiso 1 1 calc R U . . . C15 C 0.3533(2) -0.1185(2) 1.2509(2) 0.0206(5) Uani 1 1 d . . . . . H15 H 0.2618 -0.0775 1.2402 0.025 Uiso 1 1 calc R U . . . C17 C 0.3610(3) -0.2052(2) 1.1428(2) 0.0294(6) Uani 1 1 d . . . . . H17A H 0.3510 -0.1475 1.0772 0.044 Uiso 1 1 calc R U . . . H17B H 0.2865 -0.2771 1.1306 0.044 Uiso 1 1 calc R U . . . H17C H 0.4503 -0.2460 1.1519 0.044 Uiso 1 1 calc R U . . . C19 C 0.6050(2) 0.4813(2) 1.3310(2) 0.0244(5) Uani 1 1 d . . . . . H19A H 0.7045 0.4698 1.3455 0.037 Uiso 1 1 calc R U . . . H19B H 0.5676 0.4630 1.3999 0.037 Uiso 1 1 calc R U . . . H19C H 0.5884 0.5747 1.3098 0.037 Uiso 1 1 calc R U . . . C20 C 0.5927(3) 0.4113(2) 1.1260(2) 0.0246(5) Uani 1 1 d . . . . . H20A H 0.5474 0.3480 1.0638 0.037 Uiso 1 1 calc R U . . . H20B H 0.6922 0.3998 1.1406 0.037 Uiso 1 1 calc R U . . . H20C H 0.5761 0.5047 1.1049 0.037 Uiso 1 1 calc R U . . . C18 C 0.5339(2) 0.3821(2) 1.23379(18) 0.0172(5) Uani 1 1 d . . . . . H18 H 0.4330 0.3972 1.2183 0.021 Uiso 1 1 calc R U . . . C3 C 0.0837(2) 0.2315(2) 1.27786(18) 0.0168(5) Uani 1 1 d . . . . . H3A H 0.0471 0.3125 1.3100 0.020 Uiso 1 1 calc R U . . . H3B H 0.0227 0.1510 1.2868 0.020 Uiso 1 1 calc R U . . . 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 I1 0.01752(8) 0.01612(8) 0.01504(7) -0.00041(5) 0.00471(5) 0.00190(5) N1 0.0093(8) 0.0125(9) 0.0133(9) -0.0007(7) 0.0022(7) 0.0024(7) C1 0.0125(10) 0.0087(10) 0.0157(10) -0.0006(8) 0.0014(8) -0.0017(8) I2 0.01867(8) 0.03854(10) 0.01721(8) 0.00791(7) 0.00513(6) 0.00617(7) C2 0.0115(10) 0.0169(11) 0.0144(10) 0.0001(8) 0.0000(8) 0.0056(8) Se3 0.01521(11) 0.02015(12) 0.01305(10) -0.00097(8) 0.00216(8) 0.00478(9) C4 0.0146(11) 0.0200(12) 0.0149(10) 0.0001(9) 0.0050(9) 0.0049(9) C5 0.0100(10) 0.0171(11) 0.0103(10) -0.0002(8) 0.0011(8) 0.0037(8) C6 0.0128(10) 0.0174(11) 0.0139(10) 0.0013(8) 0.0038(8) 0.0027(8) C7 0.0176(11) 0.0174(11) 0.0207(11) 0.0043(9) 0.0040(9) 0.0050(9) C8 0.0115(11) 0.0253(13) 0.0266(12) 0.0022(10) 0.0029(9) 0.0057(9) C9 0.0119(10) 0.0191(12) 0.0217(11) -0.0002(9) 0.0028(9) -0.0021(9) C10 0.0163(11) 0.0163(11) 0.0100(10) 0.0002(8) 0.0021(8) 0.0028(8) C11 0.0262(13) 0.0185(12) 0.0209(12) 0.0020(9) 0.0048(10) 0.0118(10) C12 0.0132(11) 0.0339(14) 0.0189(12) -0.0053(10) 0.0005(9) 0.0019(10) C13 0.0262(13) 0.0353(15) 0.0209(12) 0.0085(11) 0.0101(10) 0.0132(11) C14 0.0170(12) 0.0349(14) 0.0173(11) -0.0094(10) 0.0034(9) 0.0010(10) C16 0.0249(13) 0.0211(13) 0.0491(17) 0.0158(12) 0.0147(12) 0.0031(10) C15 0.0134(11) 0.0147(11) 0.0337(13) 0.0040(10) 0.0034(10) 0.0020(9) C17 0.0264(13) 0.0168(13) 0.0412(15) -0.0036(11) -0.0032(11) 0.0019(10) C19 0.0237(13) 0.0200(13) 0.0283(13) -0.0080(10) 0.0048(10) -0.0032(10) C20 0.0300(13) 0.0191(12) 0.0239(12) 0.0045(10) 0.0044(10) -0.0047(10) C18 0.0158(11) 0.0149(11) 0.0205(11) 0.0005(9) 0.0022(9) 0.0004(9) C3 0.0134(11) 0.0215(12) 0.0157(11) 0.0000(9) 0.0030(9) 0.0036(9) _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 I1 Se3 2.8192(6) . ? I1 I2 2.8943(5) . ? N1 C1 1.315(3) . ? N1 C5 1.463(2) . ? N1 C4 1.530(3) . ? C1 C2 1.523(3) . ? C1 Se3 1.854(2) . ? C2 C12 1.528(3) . ? C2 C3 1.539(3) . ? C2 C11 1.547(3) . ? C4 C13 1.518(3) . ? C4 C14 1.522(3) . ? C4 C3 1.531(3) . ? C5 C6 1.404(3) . ? C5 C10 1.411(3) . ? C6 C7 1.388(3) . ? C6 C15 1.523(3) . ? C7 C8 1.385(3) . ? C7 H7 0.9500 . ? C8 C9 1.380(3) . ? C8 H8 0.9500 . ? C9 C10 1.396(3) . ? C9 H9 0.9500 . ? C10 C18 1.521(3) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C16 C15 1.537(3) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C15 C17 1.541(3) . ? C15 H15 1.0000 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C19 C18 1.535(3) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 C18 1.537(3) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C18 H18 1.0000 . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? 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 Se3 I1 I2 171.456(8) . . ? C1 N1 C5 124.08(17) . . ? C1 N1 C4 113.96(16) . . ? C5 N1 C4 121.86(16) . . ? N1 C1 C2 111.30(17) . . ? N1 C1 Se3 120.83(15) . . ? C2 C1 Se3 127.87(15) . . ? C1 C2 C12 112.81(18) . . ? C1 C2 C3 102.05(16) . . ? C12 C2 C3 110.70(18) . . ? C1 C2 C11 108.29(17) . . ? C12 C2 C11 110.59(18) . . ? C3 C2 C11 112.14(18) . . ? C1 Se3 I1 111.89(6) . . ? C13 C4 C14 109.32(19) . . ? C13 C4 N1 111.16(17) . . ? C14 C4 N1 110.18(17) . . ? C13 C4 C3 112.04(19) . . ? C14 C4 C3 113.19(18) . . ? N1 C4 C3 100.72(16) . . ? C6 C5 C10 122.25(19) . . ? C6 C5 N1 119.15(18) . . ? C10 C5 N1 118.60(18) . . ? C7 C6 C5 117.4(2) . . ? C7 C6 C15 117.95(19) . . ? C5 C6 C15 124.61(19) . . ? C8 C7 C6 121.7(2) . . ? C8 C7 H7 119.1 . . ? C6 C7 H7 119.1 . . ? C9 C8 C7 119.8(2) . . ? C9 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C8 C9 C10 121.4(2) . . ? C8 C9 H9 119.3 . . ? C10 C9 H9 119.3 . . ? C9 C10 C5 117.17(19) . . ? C9 C10 C18 117.54(19) . . ? C5 C10 C18 125.17(19) . . ? C2 C11 H11A 109.5 . . ? C2 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C2 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C2 C12 H12A 109.5 . . ? C2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C4 C13 H13A 109.5 . . ? C4 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C4 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C4 C14 H14A 109.5 . . ? C4 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C4 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C6 C15 C16 111.5(2) . . ? C6 C15 C17 109.98(19) . . ? C16 C15 C17 110.0(2) . . ? C6 C15 H15 108.4 . . ? C16 C15 H15 108.4 . . ? C17 C15 H15 108.4 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C10 C18 C19 112.23(18) . . ? C10 C18 C20 109.71(18) . . ? C19 C18 C20 109.33(19) . . ? C10 C18 H18 108.5 . . ? C19 C18 H18 108.5 . . ? C20 C18 H18 108.5 . . ? C4 C3 C2 108.41(17) . . ? C4 C3 H3A 110.0 . . ? C2 C3 H3A 110.0 . . ? C4 C3 H3B 110.0 . . ? C2 C3 H3B 110.0 . . ? H3A C3 H3B 108.4 . . ? 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 C5 N1 C1 C2 -174.76(18) . . . . ? C4 N1 C1 C2 1.6(2) . . . . ? C5 N1 C1 Se3 4.7(3) . . . . ? C4 N1 C1 Se3 -178.93(14) . . . . ? N1 C1 C2 C12 -131.38(19) . . . . ? Se3 C1 C2 C12 49.2(3) . . . . ? N1 C1 C2 C3 -12.6(2) . . . . ? Se3 C1 C2 C3 168.06(15) . . . . ? N1 C1 C2 C11 105.9(2) . . . . ? Se3 C1 C2 C11 -73.5(2) . . . . ? N1 C1 Se3 I1 -167.01(14) . . . . ? C2 C1 Se3 I1 12.3(2) . . . . ? C1 N1 C4 C13 128.9(2) . . . . ? C5 N1 C4 C13 -54.6(3) . . . . ? C1 N1 C4 C14 -109.7(2) . . . . ? C5 N1 C4 C14 66.8(2) . . . . ? C1 N1 C4 C3 10.1(2) . . . . ? C5 N1 C4 C3 -173.45(18) . . . . ? C1 N1 C5 C6 -94.2(2) . . . . ? C4 N1 C5 C6 89.7(2) . . . . ? C1 N1 C5 C10 85.8(3) . . . . ? C4 N1 C5 C10 -90.3(2) . . . . ? C10 C5 C6 C7 4.1(3) . . . . ? N1 C5 C6 C7 -175.89(18) . . . . ? C10 C5 C6 C15 -172.5(2) . . . . ? N1 C5 C6 C15 7.5(3) . . . . ? C5 C6 C7 C8 0.5(3) . . . . ? C15 C6 C7 C8 177.3(2) . . . . ? C6 C7 C8 C9 -3.1(3) . . . . ? C7 C8 C9 C10 1.2(3) . . . . ? C8 C9 C10 C5 3.1(3) . . . . ? C8 C9 C10 C18 -173.2(2) . . . . ? C6 C5 C10 C9 -5.9(3) . . . . ? N1 C5 C10 C9 174.14(18) . . . . ? C6 C5 C10 C18 170.15(19) . . . . ? N1 C5 C10 C18 -9.8(3) . . . . ? C7 C6 C15 C16 56.8(3) . . . . ? C5 C6 C15 C16 -126.6(2) . . . . ? C7 C6 C15 C17 -65.5(3) . . . . ? C5 C6 C15 C17 111.1(2) . . . . ? C9 C10 C18 C19 -58.6(3) . . . . ? C5 C10 C18 C19 125.4(2) . . . . ? C9 C10 C18 C20 63.1(2) . . . . ? C5 C10 C18 C20 -112.9(2) . . . . ? C13 C4 C3 C2 -135.72(19) . . . . ? C14 C4 C3 C2 100.1(2) . . . . ? N1 C4 C3 C2 -17.5(2) . . . . ? C1 C2 C3 C4 18.6(2) . . . . ? C12 C2 C3 C4 138.92(19) . . . . ? C11 C2 C3 C4 -97.1(2) . . . . ? _refine_diff_density_max 0.769 _refine_diff_density_min -0.746 _refine_diff_density_rms 0.084 _database_code_depnum_ccdc_archive 'CCDC 933420' ####################################################################### # # 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_8 #TrackingRef 'nikita_pub.cif' _audit_creation_method SHELXL-2012 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H31 I2 N Te' _chemical_formula_sum 'C20 H31 I2 N Te' _chemical_formula_weight 666.86 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0015 0.0009 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Te Te -0.9710 1.0960 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.8919 1.1868 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 21/n' _space_group_name_Hall '-P 2yn' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.108(2) _cell_length_b 16.440(2) _cell_length_c 12.754(2) _cell_angle_alpha 90 _cell_angle_beta 99.76(2) _cell_angle_gamma 90 _cell_volume 2295.4(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8511 _cell_measurement_theta_min 2.5575 _cell_measurement_theta_max 21.637 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_density_diffrn 1.930 _exptl_crystal_F_000 1264 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.090 _exptl_crystal_size_mid 0.085 _exptl_crystal_size_min 0.058 _exptl_absorpt_coefficient_mu 2.116 _shelx_estimated_absorpt_T_min 0.832 _shelx_estimated_absorpt_T_max 0.887 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.7503 _exptl_absorpt_correction_T_max 0.8140 _exptl_absorpt_process_details SADABS-2012/1 _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.56086 _diffrn_radiation_type AgK\a _diffrn_source 'INCOATEC Ag Microsource' _diffrn_measurement_device_type 'Bruker Smart APEX II Quazar' _diffrn_measurement_method 'omega and phi scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 108910 _diffrn_reflns_av_unetI/netI 0.0402 _diffrn_reflns_av_R_equivalents 0.0922 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.609 _diffrn_reflns_theta_max 24.813 _diffrn_reflns_theta_full 19.665 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.995 _diffrn_reflns_point_group_measured_fraction_full 1.000 _reflns_number_total 8016 _reflns_number_gt 6566 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'APEX2 v2012.2' _computing_cell_refinement 'SAINT V7.68A' _computing_data_reduction 'SAINT V7.68A' _computing_structure_solution 'SHELXL-2012 (Sheldrick, 2012)' _computing_structure_refinement 'SHELXL-2012 (Sheldrick, 2012)' _computing_molecular_graphics 'Mercury Version 2.4' _computing_publication_material 'Mercury Version 2.4' _refine_special_details ; ? ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0150P)^2^+0.1435P] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary ? _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00047(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 8016 _refine_ls_number_parameters 230 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0484 _refine_ls_R_factor_gt 0.0313 _refine_ls_wR_factor_ref 0.0492 _refine_ls_wR_factor_gt 0.0458 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.18209(2) 0.48220(2) 0.52239(2) 0.01164(4) Uani 1 1 d . . . . . I2 I 0.15389(2) 0.66619(2) 0.56417(2) 0.01691(4) Uani 1 1 d . . . . . Te1 Te 0.19930(2) 0.31498(2) 0.47634(2) 0.01111(4) Uani 1 1 d . . . . . N1 N 0.41746(19) 0.20787(12) 0.52613(15) 0.0092(4) Uani 1 1 d . . . . . C1 C 0.3774(2) 0.28028(14) 0.54432(18) 0.0091(4) Uani 1 1 d D . . . . C2 C 0.4701(2) 0.32815(15) 0.62118(19) 0.0127(5) Uani 1 1 d D . . . . C3 C 0.5811(4) 0.2697(2) 0.6406(5) 0.0162(10) Uani 0.878(18) 1 d D . P A 1 H3A H 0.6466 0.2900 0.6036 0.019 Uiso 0.878(18) 1 calc R U P A 1 H3B H 0.6139 0.2662 0.7177 0.019 Uiso 0.878(18) 1 calc R U P A 1 C4 C 0.5379(2) 0.18527(15) 0.59748(19) 0.0125(5) Uani 1 1 d D . . . . C5 C 0.6281(3) 0.14842(17) 0.5345(2) 0.0194(6) Uani 1 1 d . . . . . H5A H 0.7009 0.1303 0.5834 0.029 Uiso 1 1 calc R U . . . H5B H 0.6514 0.1893 0.4857 0.029 Uiso 1 1 calc R U . . . H5C H 0.5904 0.1018 0.4937 0.029 Uiso 1 1 calc R U . . . C6 C 0.5119(3) 0.12517(19) 0.6813(2) 0.0247(6) Uani 1 1 d . . . . . H6A H 0.5871 0.1147 0.7317 0.037 Uiso 1 1 calc R U . . . H6B H 0.4817 0.0741 0.6468 0.037 Uiso 1 1 calc R U . . . H6C H 0.4500 0.1479 0.7193 0.037 Uiso 1 1 calc R U . . . C7 C 0.5087(2) 0.40337(17) 0.5642(2) 0.0185(6) Uani 1 1 d . . . . . H7A H 0.4400 0.4414 0.5497 0.028 Uiso 1 1 calc R U . . . H7B H 0.5332 0.3869 0.4970 0.028 Uiso 1 1 calc R U . . . H7C H 0.5777 0.4299 0.6095 0.028 Uiso 1 1 calc R U . . . C8 C 0.4202(3) 0.35183(16) 0.7213(2) 0.0170(5) Uani 1 1 d . . . . . H8A H 0.3961 0.3027 0.7560 0.025 Uiso 1 1 calc R U . . . H8B H 0.3489 0.3873 0.7019 0.025 Uiso 1 1 calc R U . . . H8C H 0.4834 0.3807 0.7702 0.025 Uiso 1 1 calc R U . . . C9 C 0.3571(2) 0.15310(13) 0.44391(18) 0.0088(4) Uani 1 1 d . . . . . C10 C 0.3923(2) 0.15908(15) 0.34312(19) 0.0115(5) Uani 1 1 d . . . . . C11 C 0.3436(2) 0.10224(15) 0.2662(2) 0.0146(5) Uani 1 1 d . . . . . H11 H 0.3665 0.1041 0.1977 0.018 Uiso 1 1 calc R U . . . C12 C 0.2627(2) 0.04333(15) 0.2881(2) 0.0151(5) Uani 1 1 d . . . . . H12 H 0.2334 0.0036 0.2359 0.018 Uiso 1 1 calc R U . . . C13 C 0.2244(2) 0.04209(15) 0.3856(2) 0.0140(5) Uani 1 1 d . . . . . H13 H 0.1655 0.0030 0.3981 0.017 Uiso 1 1 calc R U . . . C14 C 0.2700(2) 0.09682(14) 0.46634(19) 0.0119(5) Uani 1 1 d . . . . . C15 C 0.2171(3) 0.09418(16) 0.5687(2) 0.0184(6) Uani 1 1 d . . . . . H15 H 0.2571 0.1380 0.6169 0.022 Uiso 1 1 calc R U . . . C16 C 0.0792(3) 0.11090(18) 0.5460(3) 0.0298(7) Uani 1 1 d . . . . . H16A H 0.0461 0.1069 0.6123 0.045 Uiso 1 1 calc R U . . . H16B H 0.0390 0.0708 0.4949 0.045 Uiso 1 1 calc R U . . . H16C H 0.0645 0.1657 0.5162 0.045 Uiso 1 1 calc R U . . . C17 C 0.2404(3) 0.01241(17) 0.6270(2) 0.0283(7) Uani 1 1 d . . . . . H17A H 0.3276 -0.0008 0.6362 0.042 Uiso 1 1 calc R U . . . H17B H 0.1931 -0.0304 0.5852 0.042 Uiso 1 1 calc R U . . . H17C H 0.2153 0.0162 0.6969 0.042 Uiso 1 1 calc R U . . . C18 C 0.4756(2) 0.22610(15) 0.3136(2) 0.0137(5) Uani 1 1 d . . . . . H18 H 0.5156 0.2531 0.3808 0.016 Uiso 1 1 calc R U . . . C19 C 0.5764(3) 0.19392(18) 0.2562(2) 0.0201(6) Uani 1 1 d . . . . . H19A H 0.6314 0.2385 0.2453 0.030 Uiso 1 1 calc R U . . . H19B H 0.5396 0.1712 0.1872 0.030 Uiso 1 1 calc R U . . . H19C H 0.6227 0.1514 0.2995 0.030 Uiso 1 1 calc R U . . . C20 C 0.3997(3) 0.29045(17) 0.2443(2) 0.0197(6) Uani 1 1 d . . . . . H20A H 0.3322 0.3083 0.2793 0.030 Uiso 1 1 calc R U . . . H20B H 0.3668 0.2670 0.1747 0.030 Uiso 1 1 calc R U . . . H20C H 0.4516 0.3371 0.2348 0.030 Uiso 1 1 calc R U . . . C3A C 0.558(3) 0.2591(13) 0.673(2) 0.0162(10) Uani 0.122(18) 1 d D . P A 2 H3A1 H 0.6438 0.2775 0.6815 0.019 Uiso 0.122(18) 1 calc R U P A 2 H3A2 H 0.5391 0.2444 0.7434 0.019 Uiso 0.122(18) 1 calc R U P A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.01050(8) 0.01143(8) 0.01303(7) 0.00105(6) 0.00215(6) 0.00248(6) I2 0.02006(9) 0.01129(8) 0.02008(9) -0.00155(6) 0.00539(7) 0.00056(7) Te1 0.00998(8) 0.01025(8) 0.01245(8) -0.00125(6) 0.00004(6) 0.00165(6) N1 0.0101(10) 0.0096(9) 0.0082(9) -0.0001(7) 0.0023(8) 0.0025(8) C1 0.0097(11) 0.0095(11) 0.0083(10) 0.0018(8) 0.0023(9) 0.0021(9) C2 0.0123(12) 0.0130(11) 0.0119(11) -0.0005(9) -0.0009(9) 0.0020(10) C3 0.0150(16) 0.0156(14) 0.017(2) -0.0058(13) -0.0012(13) 0.0027(12) C4 0.0133(12) 0.0128(11) 0.0099(11) -0.0027(9) -0.0018(9) 0.0028(9) C5 0.0154(13) 0.0263(15) 0.0168(13) -0.0009(10) 0.0032(10) 0.0077(11) C6 0.0253(16) 0.0295(16) 0.0186(14) 0.0137(12) 0.0020(12) 0.0071(13) C7 0.0110(13) 0.0231(14) 0.0210(13) 0.0010(10) 0.0016(10) -0.0072(11) C8 0.0210(14) 0.0207(13) 0.0093(11) -0.0053(9) 0.0025(10) -0.0002(11) C9 0.0103(11) 0.0084(10) 0.0076(10) -0.0018(8) 0.0017(8) 0.0031(9) C10 0.0099(11) 0.0132(11) 0.0117(11) 0.0008(9) 0.0030(9) 0.0029(9) C11 0.0178(13) 0.0168(12) 0.0086(11) -0.0008(9) 0.0006(10) 0.0053(10) C12 0.0173(13) 0.0122(11) 0.0135(12) -0.0035(9) -0.0037(10) 0.0045(10) C13 0.0119(12) 0.0104(11) 0.0197(13) -0.0015(9) 0.0027(10) 0.0010(9) C14 0.0159(13) 0.0083(11) 0.0125(11) 0.0007(8) 0.0056(10) 0.0034(9) C15 0.0260(15) 0.0123(12) 0.0211(13) -0.0022(10) 0.0162(12) -0.0048(11) C16 0.0264(17) 0.0221(15) 0.048(2) -0.0104(13) 0.0268(15) -0.0044(13) C17 0.048(2) 0.0186(14) 0.0216(15) 0.0013(11) 0.0167(14) -0.0072(14) C18 0.0145(13) 0.0164(12) 0.0107(11) 0.0010(9) 0.0038(9) -0.0016(10) C19 0.0170(14) 0.0284(15) 0.0164(13) -0.0018(11) 0.0074(11) -0.0008(11) C20 0.0211(14) 0.0227(14) 0.0168(13) 0.0063(10) 0.0075(11) -0.0014(11) C3A 0.0150(16) 0.0156(14) 0.017(2) -0.0058(13) -0.0012(13) 0.0027(12) _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 I1 Te1 2.8244(4) . ? I1 I2 3.0964(4) . ? Te1 C1 2.100(2) . ? N1 C1 1.305(3) . ? N1 C9 1.457(3) . ? N1 C4 1.531(3) . ? C1 C2 1.516(3) . ? C2 C8 1.526(4) . ? C2 C7 1.532(4) . ? C2 C3 1.549(4) . ? C2 C3A 1.566(15) . ? C3 C4 1.539(4) . ? C4 C5 1.513(4) . ? C4 C6 1.519(4) . ? C4 C3A 1.538(16) . ? C9 C14 1.402(3) . ? C9 C10 1.409(3) . ? C10 C11 1.396(3) . ? C10 C18 1.527(3) . ? C11 C12 1.381(4) . ? C12 C13 1.382(4) . ? C13 C14 1.396(3) . ? C14 C15 1.521(4) . ? C15 C16 1.535(4) . ? C15 C17 1.537(4) . ? C18 C19 1.531(4) . ? C18 C20 1.536(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 Te1 I1 I2 177.431(8) . . ? C1 Te1 I1 105.71(6) . . ? C1 N1 C9 124.2(2) . . ? C1 N1 C4 113.93(19) . . ? C9 N1 C4 121.83(18) . . ? N1 C1 C2 111.9(2) . . ? N1 C1 Te1 120.00(17) . . ? C2 C1 Te1 127.96(16) . . ? C1 C2 C8 111.7(2) . . ? C1 C2 C7 109.1(2) . . ? C8 C2 C7 111.2(2) . . ? C1 C2 C3 102.5(2) . . ? C8 C2 C3 114.6(3) . . ? C7 C2 C3 107.3(3) . . ? C1 C2 C3A 101.6(8) . . ? C8 C2 C3A 97.1(14) . . ? C7 C2 C3A 125.4(16) . . ? C4 C3 C2 108.1(2) . . ? C5 C4 C6 109.6(2) . . ? C5 C4 N1 111.9(2) . . ? C6 C4 N1 108.9(2) . . ? C5 C4 C3A 127.5(16) . . ? C6 C4 C3A 95.7(15) . . ? N1 C4 C3A 101.4(7) . . ? C5 C4 C3 110.9(3) . . ? C6 C4 C3 114.8(3) . . ? N1 C4 C3 100.5(2) . . ? C14 C9 C10 122.7(2) . . ? C14 C9 N1 120.7(2) . . ? C10 C9 N1 116.6(2) . . ? C11 C10 C9 117.4(2) . . ? C11 C10 C18 119.2(2) . . ? C9 C10 C18 123.3(2) . . ? C12 C11 C10 121.0(2) . . ? C11 C12 C13 120.2(2) . . ? C12 C13 C14 121.7(2) . . ? C13 C14 C9 116.8(2) . . ? C13 C14 C15 118.0(2) . . ? C9 C14 C15 125.0(2) . . ? C14 C15 C16 110.6(2) . . ? C14 C15 C17 112.5(2) . . ? C16 C15 C17 109.2(2) . . ? C10 C18 C19 113.0(2) . . ? C10 C18 C20 110.0(2) . . ? C19 C18 C20 109.8(2) . . ? C4 C3A C2 107.3(10) . . ? _refine_diff_density_max 0.829 _refine_diff_density_min -0.748 _refine_diff_density_rms 0.145 _database_code_depnum_ccdc_archive 'CCDC 933421'