# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Cesar, Vincent' 'Tourneux, Jean-Christophe' 'Vujkovic, Nadia' 'Brousses, Remy' 'Lugan, Noel' 'Lavigne, Guy' _publ_contact_author_name 'Lavigne, Guy' _publ_contact_author_email lavigne@lcc-toulouse.fr _publ_section_title ; Interplay between an elusive 4-(isopropylamino)imidazol-2-ylidene and its isolable mesoionic tautomer, and associated reactivities ; data_compound_3 _database_code_depnum_ccdc_archive 'CCDC 859204' #TrackingRef '- all_compounds.cif' _audit_creation_date 2010-08-03T14:01:05-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C25 H32 F3 N3 O3 S' _chemical_formula_moiety 'C24 H32 N3, C F3 O3 S' _chemical_formula_weight 511.6 _chemical_absolute_configuration ad _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _space_group_crystal_system orthorhobic _space_group_name_H-M_alt 'P n a 21' _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_Int_Tables_number 33 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 15.974(5) _cell_length_b 13.378(5) _cell_length_c 12.495(5) _cell_angle_alpha 90.0 _cell_angle_beta 90.0 _cell_angle_gamma 90.0 _cell_volume 2670.2(17) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_theta_min 2.57 _cell_measurement_reflns_used 9999 _cell_measurement_theta_max 36.29 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1080 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.172 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; 'SADABS, Sheldrick, Bruker, 2000' ; _exptl_absorpt_correction_T_min 0.862 _exptl_absorpt_correction_T_max 1.000 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device_type 'Bruker APEX II' _diffrn_measurement_method 'phi and omega scans' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% 0 _diffrn_reflns_av_R_equivalents 0.025 _diffrn_reflns_av_unetI/netI 0.0126 _diffrn_reflns_number 58595 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 5443 _reflns_number_gt 5206 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' #----------------------------------------------------------------------------# # 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^ > 2\s(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^)+(0.0804P)^2^+0.2173P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment riding _refine_ls_extinction_method none _refine_ls_number_reflns 5443 _refine_ls_number_parameters 327 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0348 _refine_ls_R_factor_gt 0.0323 _refine_ls_wR_factor_ref 0.0999 _refine_ls_wR_factor_gt 0.0951 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.03(5) _refine_diff_density_max 0.283 _refine_diff_density_min -0.321 _refine_diff_density_rms 0.056 #----------------------------------------------------------------------------# # 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 C1 C 0.91435(9) 0.83242(11) 0.26080(13) 0.0272(3) Uani 1 1 d . . . H1 H 0.8888 0.8918 0.2398 0.033 Uiso 1 1 calc R . . C2 C 0.98919(9) 0.69212(11) 0.25915(13) 0.0277(3) Uani 1 1 d . . . H2 H 1.0234 0.6405 0.2351 0.033 Uiso 1 1 calc R . . C3 C 0.95549(9) 0.70147(11) 0.35876(12) 0.0258(3) Uani 1 1 d . . . C4 C 1.00566(9) 0.54950(12) 0.44194(13) 0.0313(3) Uani 1 1 d . . . H4 H 1.0568 0.5578 0.3995 0.038 Uiso 1 1 calc R . . C5 C 0.95027(12) 0.47218(13) 0.38663(18) 0.0437(4) Uani 1 1 d . . . H5A H 0.9399 0.4927 0.3142 0.066 Uiso 1 1 calc R . . H5B H 0.8981 0.4667 0.4243 0.066 Uiso 1 1 calc R . . H5C H 0.978 0.4085 0.3867 0.066 Uiso 1 1 calc R . . C6 C 1.03026(11) 0.51629(15) 0.55385(17) 0.0446(4) Uani 1 1 d . . . H6A H 0.9807 0.5057 0.5958 0.067 Uiso 1 1 calc R . . H6B H 1.064 0.5671 0.5868 0.067 Uiso 1 1 calc R . . H6C H 1.0616 0.4552 0.5496 0.067 Uiso 1 1 calc R . . C11 C 0.98327(9) 0.79166(10) 0.08911(11) 0.0245(3) Uani 1 1 d . . . C12 C 1.06650(9) 0.81178(10) 0.06338(12) 0.0264(3) Uani 1 1 d . . . C13 C 1.08651(9) 0.82223(13) -0.04436(14) 0.0329(3) Uani 1 1 d . . . H13 H 1.1416 0.8359 -0.0636 0.039 Uiso 1 1 calc R . . C14 C 1.02624(10) 0.81275(13) -0.12394(13) 0.0336(3) Uani 1 1 d . . . C15 C 0.94334(10) 0.79597(12) -0.09427(13) 0.0307(3) Uani 1 1 d . . . H15 H 0.9025 0.7926 -0.1471 0.037 Uiso 1 1 calc R . . C16 C 0.92005(9) 0.78410(11) 0.01234(13) 0.0276(3) Uani 1 1 d . . . C17 C 1.13373(9) 0.81930(11) 0.14714(15) 0.0329(3) Uani 1 1 d . . . H17A H 1.1557 0.7539 0.1618 0.049 Uiso 1 1 calc R . . H17B H 1.1105 0.847 0.2115 0.049 Uiso 1 1 calc R . . H17C H 1.1779 0.8617 0.1216 0.049 Uiso 1 1 calc R . . C18 C 1.05067(13) 0.8169(2) -0.24006(17) 0.0535(5) Uani 1 1 d . . . H18A H 1.0913 0.7658 -0.2547 0.08 Uiso 1 1 calc R . . H18B H 1.0743 0.8812 -0.2559 0.08 Uiso 1 1 calc R . . H18C H 1.002 0.8063 -0.2837 0.08 Uiso 1 1 calc R . . C19 C 0.83137(10) 0.75905(14) 0.04142(14) 0.0361(3) Uani 1 1 d . . . H19A H 0.8026 0.7344 -0.0206 0.054 Uiso 1 1 calc R . . H19B H 0.8037 0.818 0.0673 0.054 Uiso 1 1 calc R . . H19C H 0.8311 0.7088 0.0962 0.054 Uiso 1 1 calc R . . C21 C 0.86857(9) 0.83209(11) 0.45099(12) 0.0269(3) Uani 1 1 d . . . C22 C 0.91629(10) 0.89175(11) 0.51767(13) 0.0302(3) Uani 1 1 d . . . C23 C 0.87824(12) 0.92685(13) 0.61033(14) 0.0377(4) Uani 1 1 d . . . H23 H 0.9087 0.9673 0.6567 0.045 Uiso 1 1 calc R . . C24 C 0.79593(13) 0.90319(13) 0.63568(15) 0.0415(4) Uani 1 1 d . . . C25 C 0.75084(11) 0.84461(14) 0.56559(17) 0.0409(4) Uani 1 1 d . . . H25 H 0.6955 0.8294 0.5819 0.049 Uiso 1 1 calc R . . C26 C 0.78511(10) 0.80759(13) 0.47157(14) 0.0335(3) Uani 1 1 d . . . C27 C 1.00622(11) 0.91726(14) 0.49207(15) 0.0399(4) Uani 1 1 d . . . H27A H 1.0083 0.9559 0.4274 0.06 Uiso 1 1 calc R . . H27B H 1.0377 0.8568 0.4828 0.06 Uiso 1 1 calc R . . H27C H 1.0298 0.9553 0.5498 0.06 Uiso 1 1 calc R . . C28 C 0.75666(17) 0.94068(18) 0.73847(19) 0.0596(6) Uani 1 1 d . . . H28A H 0.7271 0.887 0.7726 0.089 Uiso 1 1 calc R . . H28B H 0.7183 0.9939 0.7225 0.089 Uiso 1 1 calc R . . H28C H 0.7997 0.9649 0.7854 0.089 Uiso 1 1 calc R . . C29 C 0.73458(12) 0.74462(19) 0.39572(19) 0.0507(5) Uani 1 1 d . . . H29A H 0.7592 0.6794 0.3904 0.076 Uiso 1 1 calc R . . H29B H 0.7339 0.7755 0.3264 0.076 Uiso 1 1 calc R . . H29C H 0.6783 0.7388 0.422 0.076 Uiso 1 1 calc R . . C100 C 0.69765(16) 1.08894(18) 0.2690(2) 0.0588(6) Uani 1 1 d . . . N1 N 0.96258(8) 0.77478(10) 0.20019(10) 0.0259(3) Uani 1 1 d . . . N2 N 0.90903(8) 0.78985(9) 0.35751(10) 0.0261(3) Uani 1 1 d . . . N3 N 0.96400(9) 0.64744(10) 0.45032(11) 0.0294(3) Uani 1 1 d . . . O1 O 0.67257(10) 0.92623(10) 0.16937(15) 0.0563(4) Uani 1 1 d . . . O2 O 0.81032(8) 1.00233(10) 0.15775(15) 0.0492(3) Uani 1 1 d . . . O3 O 0.69354(10) 1.07701(12) 0.06528(13) 0.0546(4) Uani 1 1 d . . . F1 F 0.61670(11) 1.10571(16) 0.2753(2) 0.1192(10) Uani 1 1 d . . . F2 F 0.73625(8) 1.17698(9) 0.26823(12) 0.0568(3) Uani 1 1 d . . . F3 F 0.72060(19) 1.04288(17) 0.35792(14) 0.1210(10) Uani 1 1 d . . . S1 S 0.72115(2) 1.01491(3) 0.15164(4) 0.03179(11) Uani 1 1 d . . . H3 H 0.9180(16) 0.6507(19) 0.489(2) 0.05 Uiso 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 C1 0.0298(6) 0.0256(7) 0.0261(7) 0.0001(6) 0.0012(6) 0.0048(5) C2 0.0325(7) 0.0234(7) 0.0273(7) 0.0019(6) 0.0010(6) 0.0063(5) C3 0.0280(6) 0.0208(6) 0.0285(7) -0.0015(5) 0.0000(6) 0.0033(5) C4 0.0285(7) 0.0253(7) 0.0402(9) 0.0074(6) 0.0057(6) 0.0048(6) C5 0.0475(10) 0.0290(8) 0.0546(11) -0.0038(8) 0.0093(8) 0.0005(7) C6 0.0379(8) 0.0456(10) 0.0502(11) 0.0216(9) -0.0001(8) 0.0078(7) C11 0.0276(7) 0.0225(6) 0.0234(7) 0.0019(5) 0.0009(5) 0.0011(5) C12 0.0259(7) 0.0236(6) 0.0297(7) 0.0035(6) -0.0025(6) 0.0038(5) C13 0.0251(7) 0.0386(8) 0.0349(8) 0.0093(7) 0.0030(6) -0.0008(6) C14 0.0342(8) 0.0397(9) 0.0269(8) 0.0066(7) 0.0010(6) -0.0002(6) C15 0.0301(7) 0.0332(8) 0.0288(8) 0.0021(6) -0.0032(6) 0.0002(6) C16 0.0271(7) 0.0283(7) 0.0275(7) -0.0004(6) -0.0003(6) 0.0006(5) C17 0.0284(7) 0.0333(7) 0.0370(8) 0.0032(7) -0.0053(7) 0.0035(5) C18 0.0420(9) 0.0856(16) 0.0329(9) 0.0148(10) 0.0046(8) -0.0066(10) C19 0.0254(7) 0.0465(9) 0.0363(8) -0.0071(7) 0.0033(6) -0.0040(6) C21 0.0293(7) 0.0254(6) 0.0262(7) 0.0010(5) 0.0047(6) 0.0095(5) C22 0.0349(8) 0.0239(6) 0.0319(7) 0.0000(6) 0.0043(6) 0.0043(6) C23 0.0496(10) 0.0288(7) 0.0347(8) -0.0069(6) 0.0057(7) 0.0056(7) C24 0.0524(10) 0.0347(8) 0.0375(9) 0.0002(7) 0.0180(8) 0.0162(7) C25 0.0325(8) 0.0447(9) 0.0456(9) 0.0071(8) 0.0126(8) 0.0083(7) C26 0.0297(7) 0.0360(8) 0.0349(9) 0.0052(7) 0.0004(6) 0.0041(6) C27 0.0376(8) 0.0416(9) 0.0406(9) -0.0073(7) 0.0054(7) -0.0037(7) C28 0.0727(14) 0.0534(12) 0.0527(13) -0.0099(10) 0.0300(11) 0.0123(11) C29 0.0370(9) 0.0662(13) 0.0489(11) -0.0012(10) -0.0027(8) -0.0096(9) C100 0.0628(13) 0.0554(13) 0.0584(13) -0.0213(11) 0.0234(11) -0.0248(10) N1 0.0277(6) 0.0256(6) 0.0244(6) 0.0017(5) 0.0013(5) 0.0049(5) N2 0.0293(6) 0.0240(6) 0.0248(6) 0.0011(5) 0.0015(5) 0.0055(5) N3 0.0365(6) 0.0252(6) 0.0265(6) 0.0030(5) 0.0053(5) 0.0055(5) O1 0.0622(8) 0.0308(6) 0.0760(11) -0.0056(7) -0.0033(8) -0.0134(6) O2 0.0366(7) 0.0416(6) 0.0693(9) -0.0015(7) -0.0077(7) 0.0095(5) O3 0.0556(8) 0.0533(8) 0.0549(9) 0.0117(7) -0.0235(7) -0.0013(7) F1 0.0621(9) 0.1041(14) 0.191(2) -0.0814(16) 0.0667(13) -0.0293(9) F2 0.0576(7) 0.0410(6) 0.0719(8) -0.0220(6) 0.0093(6) -0.0126(5) F3 0.226(3) 0.0985(14) 0.0380(8) 0.0018(9) 0.0109(11) -0.0652(15) S1 0.03223(19) 0.02426(17) 0.0389(2) -0.00040(17) -0.00671(16) 0.00129(13) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 N1 1.327(2) . ? C1 N2 1.339(2) . ? C1 H1 0.93 . ? C2 C3 1.362(2) . ? C2 N1 1.3951(19) . ? C2 H2 0.93 . ? C3 N3 1.360(2) . ? C3 N2 1.3960(18) . ? C4 N3 1.473(2) . ? C4 C6 1.519(3) . ? C4 C5 1.527(3) . ? C4 H4 0.98 . ? C5 H5A 0.96 . ? C5 H5B 0.96 . ? C5 H5C 0.96 . ? C6 H6A 0.96 . ? C6 H6B 0.96 . ? C6 H6C 0.96 . ? C11 C12 1.394(2) . ? C11 C16 1.396(2) . ? C11 N1 1.4446(19) . ? C12 C13 1.391(2) . ? C12 C17 1.503(2) . ? C13 C14 1.390(2) . ? C13 H13 0.93 . ? C14 C15 1.393(2) . ? C14 C18 1.503(3) . ? C15 C16 1.392(2) . ? C15 H15 0.93 . ? C16 C19 1.500(2) . ? C17 H17A 0.96 . ? C17 H17B 0.96 . ? C17 H17C 0.96 . ? C18 H18A 0.96 . ? C18 H18B 0.96 . ? C18 H18C 0.96 . ? C19 H19A 0.96 . ? C19 H19B 0.96 . ? C19 H19C 0.96 . ? C21 C22 1.383(2) . ? C21 C26 1.397(2) . ? C21 N2 1.4496(19) . ? C22 C23 1.389(2) . ? C22 C27 1.511(2) . ? C23 C24 1.389(3) . ? C23 H23 0.93 . ? C24 C25 1.379(3) . ? C24 C28 1.515(2) . ? C25 C26 1.388(3) . ? C25 H25 0.93 . ? C26 C29 1.503(3) . ? C27 H27A 0.96 . ? C27 H27B 0.96 . ? C27 H27C 0.96 . ? C28 H28A 0.96 . ? C28 H28B 0.96 . ? C28 H28C 0.96 . ? C29 H29A 0.96 . ? C29 H29B 0.96 . ? C29 H29C 0.96 . ? C100 F1 1.315(3) . ? C100 F3 1.323(4) . ? C100 F2 1.330(2) . ? C100 S1 1.809(2) . ? N3 H3 0.88(3) . ? O1 S1 1.4349(14) . ? O2 S1 1.4364(14) . ? O3 S1 1.4316(16) . ? 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 N1 C1 N2 107.74(13) . . ? N1 C1 H1 126.1 . . ? N2 C1 H1 126.1 . . ? C3 C2 N1 106.81(13) . . ? C3 C2 H2 126.6 . . ? N1 C2 H2 126.6 . . ? N3 C3 C2 132.88(13) . . ? N3 C3 N2 120.84(13) . . ? C2 C3 N2 106.13(13) . . ? N3 C4 C6 108.15(14) . . ? N3 C4 C5 111.90(14) . . ? C6 C4 C5 111.62(15) . . ? N3 C4 H4 108.4 . . ? C6 C4 H4 108.4 . . ? C5 C4 H4 108.4 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C12 C11 C16 123.04(14) . . ? C12 C11 N1 118.03(13) . . ? C16 C11 N1 118.90(13) . . ? C13 C12 C11 117.50(13) . . ? C13 C12 C17 120.21(14) . . ? C11 C12 C17 122.27(15) . . ? C14 C13 C12 121.62(14) . . ? C14 C13 H13 119.2 . . ? C12 C13 H13 119.2 . . ? C13 C14 C15 118.86(15) . . ? C13 C14 C18 120.49(15) . . ? C15 C14 C18 120.62(15) . . ? C16 C15 C14 121.80(15) . . ? C16 C15 H15 119.1 . . ? C14 C15 H15 119.1 . . ? C15 C16 C11 117.12(14) . . ? C15 C16 C19 120.63(14) . . ? C11 C16 C19 122.17(14) . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C14 C18 H18A 109.5 . . ? C14 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C14 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C22 C21 C26 123.42(14) . . ? C22 C21 N2 117.69(13) . . ? C26 C21 N2 118.84(14) . . ? C21 C22 C23 117.13(15) . . ? C21 C22 C27 121.80(14) . . ? C23 C22 C27 121.06(16) . . ? C24 C23 C22 121.81(17) . . ? C24 C23 H23 119.1 . . ? C22 C23 H23 119.1 . . ? C25 C24 C23 118.64(16) . . ? C25 C24 C28 120.69(19) . . ? C23 C24 C28 120.7(2) . . ? C24 C25 C26 122.32(16) . . ? C24 C25 H25 118.8 . . ? C26 C25 H25 118.8 . . ? C25 C26 C21 116.66(16) . . ? C25 C26 C29 121.46(17) . . ? C21 C26 C29 121.88(16) . . ? C22 C27 H27A 109.5 . . ? C22 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C22 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C24 C28 H28A 109.5 . . ? C24 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C24 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C26 C29 H29A 109.5 . . ? C26 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C26 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? F1 C100 F3 107.5(2) . . ? F1 C100 F2 107.8(2) . . ? F3 C100 F2 106.9(2) . . ? F1 C100 S1 110.28(18) . . ? F3 C100 S1 111.62(19) . . ? F2 C100 S1 112.53(15) . . ? C1 N1 C2 109.64(13) . . ? C1 N1 C11 126.17(13) . . ? C2 N1 C11 124.16(13) . . ? C1 N2 C3 109.67(12) . . ? C1 N2 C21 126.14(12) . . ? C3 N2 C21 123.93(12) . . ? C3 N3 C4 117.26(13) . . ? C3 N3 H3 110.5(16) . . ? C4 N3 H3 117.4(17) . . ? O3 S1 O1 115.44(10) . . ? O3 S1 O2 114.43(10) . . ? O1 S1 O2 115.55(9) . . ? O3 S1 C100 103.26(12) . . ? O1 S1 C100 102.44(11) . . ? O2 S1 C100 103.12(11) . . ? data_compound_4' _database_code_depnum_ccdc_archive 'CCDC 859205' #TrackingRef '- all_compounds.cif' _audit_creation_date 2010-09-14T09:21:33-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C30 H37 N3' _chemical_formula_moiety 'C24 H31 N3, C6 H6' _chemical_formula_weight 439.63 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _space_group_crystal_system orthorhombic _space_group_name_H-M_alt 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_Int_Tables_number 19 loop_ _space_group_symop_operation_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 8.5850(9) _cell_length_b 16.0692(18) _cell_length_c 19.252(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2655.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_theta_min 2.12 _cell_measurement_reflns_used 9999 _cell_measurement_theta_max 30.61 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.099 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.064 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; 'SADABS, Sheldrick, Bruker, 2000' ; _exptl_absorpt_correction_T_min 0.6775 _exptl_absorpt_correction_T_max 0.7461 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device_type 'Bruker APEX II' _diffrn_measurement_method 'phi and omega scans' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 31420 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_sigmaI/netI 0.0188 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 26.37 _reflns_number_total 5422 _reflns_number_gt 4986 _reflns_threshold_expression >2\s(I) _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.998 #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' #----------------------------------------------------------------------------# # 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^ > 2\s(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^)+(0.0564P)^2^+0.5068P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.1(19) _refine_ls_number_reflns 5422 _refine_ls_number_parameters 314 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0408 _refine_ls_R_factor_gt 0.0355 _refine_ls_wR_factor_ref 0.0962 _refine_ls_wR_factor_gt 0.0919 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.249 _refine_diff_density_min -0.201 _refine_diff_density_rms 0.033 #----------------------------------------------------------------------------# # 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' 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 C1 C 0.94173(16) 0.50689(9) 0.07012(7) 0.0205(3) Uani 1 1 d . . . C2 C 0.77740(16) 0.40147(8) 0.05519(7) 0.0217(3) Uani 1 1 d . . . C3 C 0.76291(16) 0.42547(8) 0.12515(7) 0.0200(3) Uani 1 1 d . . . C4 C 0.58364(18) 0.32976(9) 0.16623(8) 0.0264(3) Uani 1 1 d . . . H4 H 0.6461 0.2874 0.1404 0.032 Uiso 1 1 calc R . . C5 C 0.43822(19) 0.35010(11) 0.12358(9) 0.0378(4) Uani 1 1 d . . . H5A H 0.3721 0.3888 0.1496 0.057 Uiso 1 1 calc R . . H5B H 0.3802 0.2988 0.1142 0.057 Uiso 1 1 calc R . . H5C H 0.4692 0.3758 0.0795 0.057 Uiso 1 1 calc R . . C6 C 0.5365(2) 0.29284(11) 0.23588(9) 0.0401(4) Uani 1 1 d . . . H6A H 0.6301 0.2784 0.2624 0.060 Uiso 1 1 calc R . . H6B H 0.4739 0.2427 0.2282 0.060 Uiso 1 1 calc R . . H6C H 0.4751 0.3337 0.2620 0.060 Uiso 1 1 calc R . . C11 C 0.89800(15) 0.53999(9) 0.19323(7) 0.0196(3) Uani 1 1 d . . . C12 C 0.84085(16) 0.62130(9) 0.19676(7) 0.0218(3) Uani 1 1 d . . . C13 C 0.86792(17) 0.66615(9) 0.25716(8) 0.0264(3) Uani 1 1 d . . . H13 H 0.8315 0.7219 0.2602 0.032 Uiso 1 1 calc R . . C14 C 0.94673(18) 0.63187(10) 0.31333(8) 0.0274(3) Uani 1 1 d . . . C15 C 1.00198(16) 0.55130(10) 0.30771(7) 0.0256(3) Uani 1 1 d . . . H15 H 1.0572 0.5278 0.3457 0.031 Uiso 1 1 calc R . . C16 C 0.97931(15) 0.50354(9) 0.24828(7) 0.0224(3) Uani 1 1 d . . . C17 C 0.75219(19) 0.65956(10) 0.13733(8) 0.0305(3) Uani 1 1 d . . . H17A H 0.6941 0.7081 0.1540 0.046 Uiso 1 1 calc R . . H17B H 0.6793 0.6186 0.1182 0.046 Uiso 1 1 calc R . . H17C H 0.8254 0.6769 0.1011 0.046 Uiso 1 1 calc R . . C18 C 0.9671(2) 0.68183(12) 0.37930(9) 0.0414(4) Uani 1 1 d . . . H18A H 1.0150 0.6468 0.4151 0.062 Uiso 1 1 calc R . . H18B H 0.8651 0.7012 0.3955 0.062 Uiso 1 1 calc R . . H18C H 1.0343 0.7299 0.3700 0.062 Uiso 1 1 calc R . . C19 C 1.03763(18) 0.41549(9) 0.24384(8) 0.0300(3) Uani 1 1 d . . . H19A H 1.1054 0.4038 0.2836 0.045 Uiso 1 1 calc R . . H19B H 1.0966 0.4082 0.2007 0.045 Uiso 1 1 calc R . . H19C H 0.9489 0.3771 0.2443 0.045 Uiso 1 1 calc R . . C21 C 0.93396(15) 0.45057(8) -0.04786(6) 0.0193(3) Uani 1 1 d . . . C22 C 0.85802(15) 0.50215(9) -0.09537(7) 0.0215(3) Uani 1 1 d . . . C23 C 0.90591(16) 0.49889(9) -0.16446(7) 0.0217(3) Uani 1 1 d . . . H23 H 0.8552 0.5328 -0.1979 0.026 Uiso 1 1 calc R . . C24 C 1.02677(16) 0.44678(9) -0.18528(7) 0.0204(3) Uani 1 1 d . . . C25 C 1.10011(17) 0.39679(8) -0.13604(7) 0.0219(3) Uani 1 1 d . . . H25 H 1.1835 0.3618 -0.1501 0.026 Uiso 1 1 calc R . . C26 C 1.05392(17) 0.39699(8) -0.06666(7) 0.0212(3) Uani 1 1 d . . . C27 C 0.73168(18) 0.56096(10) -0.07245(8) 0.0312(3) Uani 1 1 d . . . H27A H 0.7772 0.6053 -0.0440 0.047 Uiso 1 1 calc R . . H27B H 0.6542 0.5305 -0.0450 0.047 Uiso 1 1 calc R . . H27C H 0.6814 0.5854 -0.1134 0.047 Uiso 1 1 calc R . . C28 C 1.07693(18) 0.44370(10) -0.26037(7) 0.0274(3) Uani 1 1 d . . . H28A H 1.0189 0.4854 -0.2870 0.041 Uiso 1 1 calc R . . H28B H 1.0557 0.3882 -0.2793 0.041 Uiso 1 1 calc R . . H28C H 1.1887 0.4554 -0.2636 0.041 Uiso 1 1 calc R . . C29 C 1.1325(2) 0.34229(10) -0.01346(8) 0.0308(3) Uani 1 1 d . . . H29A H 1.2194 0.3126 -0.0352 0.046 Uiso 1 1 calc R . . H29B H 1.0572 0.3019 0.0047 0.046 Uiso 1 1 calc R . . H29C H 1.1718 0.3768 0.0247 0.046 Uiso 1 1 calc R . . C31 C 0.3218(3) 0.6088(2) 0.05582(12) 0.0685(8) Uani 1 1 d . . . H31 H 0.3951 0.5841 0.0865 0.082 Uiso 1 1 calc R . . C32 C 0.2381(4) 0.6748(2) 0.07706(13) 0.0917(12) Uani 1 1 d . . . H32 H 0.2520 0.6968 0.1224 0.110 Uiso 1 1 calc R . . C33 C 0.1296(4) 0.71096(14) 0.0312(2) 0.0942(12) Uani 1 1 d . . . H33 H 0.0693 0.7577 0.0450 0.113 Uiso 1 1 calc R . . C34 C 0.1125(3) 0.67647(15) -0.03510(14) 0.0640(7) Uani 1 1 d . . . H34 H 0.0401 0.6996 -0.0670 0.077 Uiso 1 1 calc R . . C35 C 0.1994(2) 0.61047(14) -0.05319(10) 0.0501(5) Uani 1 1 d . . . H35 H 0.1879 0.5868 -0.0981 0.060 Uiso 1 1 calc R . . C36 C 0.3026(2) 0.57756(14) -0.00833(11) 0.0529(5) Uani 1 1 d . . . H36 H 0.3634 0.5311 -0.0224 0.063 Uiso 1 1 calc R . . N1 N 0.87116(13) 0.49234(7) 0.13145(6) 0.0203(2) Uani 1 1 d . . . N2 N 0.88702(13) 0.45350(7) 0.02415(6) 0.0204(2) Uani 1 1 d . . . N3 N 0.68187(14) 0.40182(7) 0.17910(6) 0.0228(3) Uani 1 1 d . . . H2 H 0.723(2) 0.3591(10) 0.0285(8) 0.026(4) Uiso 1 1 d . . . H1 H 1.0168(19) 0.5473(10) 0.0619(8) 0.024(4) Uiso 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 C1 0.0216(6) 0.0222(6) 0.0177(6) -0.0016(5) 0.0019(5) -0.0037(6) C2 0.0227(7) 0.0216(6) 0.0207(6) -0.0012(5) 0.0033(5) -0.0061(6) C3 0.0207(6) 0.0181(6) 0.0213(6) -0.0014(5) 0.0004(5) -0.0013(5) C4 0.0284(8) 0.0254(7) 0.0253(7) -0.0033(6) 0.0073(6) -0.0071(6) C5 0.0280(8) 0.0439(10) 0.0416(9) -0.0047(7) 0.0031(7) -0.0111(7) C6 0.0507(10) 0.0361(9) 0.0334(9) 0.0019(7) 0.0125(8) -0.0181(8) C11 0.0181(6) 0.0235(6) 0.0171(6) -0.0034(5) 0.0030(5) -0.0052(5) C12 0.0213(7) 0.0233(7) 0.0207(6) 0.0009(5) 0.0010(5) -0.0015(5) C13 0.0255(7) 0.0245(7) 0.0292(7) -0.0071(6) 0.0032(6) 0.0007(6) C14 0.0218(7) 0.0362(8) 0.0243(7) -0.0097(6) 0.0010(6) -0.0034(6) C15 0.0206(6) 0.0358(8) 0.0204(7) -0.0023(6) -0.0025(5) 0.0006(6) C16 0.0191(6) 0.0251(7) 0.0229(6) -0.0008(5) 0.0012(5) -0.0002(6) C17 0.0337(8) 0.0312(8) 0.0265(7) 0.0023(6) -0.0019(7) 0.0042(7) C18 0.0367(9) 0.0532(11) 0.0341(9) -0.0223(8) -0.0053(7) 0.0047(8) C19 0.0293(7) 0.0303(8) 0.0304(8) -0.0008(6) -0.0010(6) 0.0051(6) C21 0.0222(6) 0.0209(6) 0.0146(6) -0.0017(5) 0.0025(5) -0.0047(5) C22 0.0201(6) 0.0213(7) 0.0233(6) -0.0016(5) -0.0003(5) -0.0025(6) C23 0.0231(6) 0.0226(7) 0.0193(6) 0.0034(5) -0.0036(5) -0.0013(6) C24 0.0233(7) 0.0221(7) 0.0158(6) -0.0003(5) -0.0004(5) -0.0042(5) C25 0.0242(7) 0.0213(6) 0.0201(6) 0.0001(5) 0.0019(5) 0.0020(5) C26 0.0250(6) 0.0197(6) 0.0189(6) 0.0012(5) -0.0006(5) -0.0010(5) C27 0.0277(7) 0.0367(8) 0.0293(7) -0.0010(6) 0.0002(6) 0.0097(7) C28 0.0320(7) 0.0330(8) 0.0174(6) 0.0030(6) 0.0018(6) 0.0025(6) C29 0.0388(8) 0.0338(8) 0.0199(7) 0.0044(6) 0.0010(6) 0.0120(7) C31 0.0468(12) 0.109(2) 0.0497(12) 0.0143(14) -0.0126(10) -0.0379(14) C32 0.118(3) 0.106(2) 0.0517(14) -0.0309(15) 0.0255(16) -0.084(2) C33 0.092(2) 0.0296(11) 0.161(3) -0.0118(15) 0.075(2) -0.0255(13) C34 0.0529(13) 0.0576(13) 0.0815(17) 0.0410(13) 0.0027(12) -0.0167(11) C35 0.0459(11) 0.0711(14) 0.0334(9) 0.0066(9) 0.0050(8) -0.0283(10) C36 0.0330(9) 0.0672(13) 0.0585(12) 0.0031(10) 0.0144(9) -0.0112(9) N1 0.0221(6) 0.0218(6) 0.0171(5) -0.0018(4) 0.0023(4) -0.0044(5) N2 0.0215(5) 0.0223(6) 0.0172(5) -0.0015(4) 0.0019(4) -0.0034(5) N3 0.0240(6) 0.0249(6) 0.0196(5) -0.0024(5) 0.0051(5) -0.0051(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1 N2 1.3190(17) . ? C1 N1 1.3477(17) . ? C1 H1 0.929(17) . ? C2 N2 1.3935(17) . ? C2 C3 1.4065(18) . ? C2 H2 0.972(17) . ? C3 N3 1.3066(17) . ? C3 N1 1.4259(17) . ? C4 N3 1.4537(18) . ? C4 C6 1.521(2) . ? C4 C5 1.530(2) . ? C4 H4 1.0000 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C11 C12 1.397(2) . ? C11 C16 1.3977(19) . ? C11 N1 1.4331(17) . ? C12 C13 1.388(2) . ? C12 C17 1.506(2) . ? C13 C14 1.389(2) . ? C13 H13 0.9500 . ? C14 C15 1.383(2) . ? C14 C18 1.513(2) . ? C15 C16 1.391(2) . ? C15 H15 0.9500 . ? C16 C19 1.503(2) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C21 C26 1.3903(19) . ? C21 C22 1.3959(19) . ? C21 N2 1.4445(16) . ? C22 C23 1.3932(19) . ? C22 C27 1.5047(19) . ? C23 C24 1.392(2) . ? C23 H23 0.9500 . ? C24 C25 1.3930(19) . ? C24 C28 1.5094(18) . ? C25 C26 1.3933(18) . ? C25 H25 0.9500 . ? C26 C29 1.5087(19) . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C31 C36 1.343(3) . ? C31 C32 1.345(5) . ? C31 H31 0.9500 . ? C32 C33 1.408(5) . ? C32 H32 0.9500 . ? C33 C34 1.400(4) . ? C33 H33 0.9500 . ? C34 C35 1.343(3) . ? C34 H34 0.9500 . ? C35 C36 1.345(3) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? 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 N2 C1 N1 108.36(12) . . ? N2 C1 H1 125.9(10) . . ? N1 C1 H1 125.7(10) . . ? N2 C2 C3 107.81(12) . . ? N2 C2 H2 121.2(10) . . ? C3 C2 H2 130.9(10) . . ? N3 C3 C2 136.76(13) . . ? N3 C3 N1 119.91(11) . . ? C2 C3 N1 103.33(11) . . ? N3 C4 C6 108.35(12) . . ? N3 C4 C5 113.25(13) . . ? C6 C4 C5 109.84(14) . . ? N3 C4 H4 108.4 . . ? C6 C4 H4 108.4 . . ? C5 C4 H4 108.4 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C12 C11 C16 122.02(13) . . ? C12 C11 N1 118.92(12) . . ? C16 C11 N1 119.06(12) . . ? C13 C12 C11 117.88(13) . . ? C13 C12 C17 120.63(13) . . ? C11 C12 C17 121.49(13) . . ? C12 C13 C14 121.86(14) . . ? C12 C13 H13 119.1 . . ? C14 C13 H13 119.1 . . ? C15 C14 C13 118.51(13) . . ? C15 C14 C18 121.53(15) . . ? C13 C14 C18 119.95(15) . . ? C14 C15 C16 122.18(14) . . ? C14 C15 H15 118.9 . . ? C16 C15 H15 118.9 . . ? C15 C16 C11 117.54(13) . . ? C15 C16 C19 121.28(13) . . ? C11 C16 C19 121.17(13) . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C14 C18 H18A 109.5 . . ? C14 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C14 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C26 C21 C22 122.89(12) . . ? C26 C21 N2 118.47(11) . . ? C22 C21 N2 118.64(12) . . ? C23 C22 C21 117.74(12) . . ? C23 C22 C27 121.08(13) . . ? C21 C22 C27 121.16(12) . . ? C24 C23 C22 121.16(12) . . ? C24 C23 H23 119.4 . . ? C22 C23 H23 119.4 . . ? C23 C24 C25 119.19(12) . . ? C23 C24 C28 120.54(12) . . ? C25 C24 C28 120.26(12) . . ? C26 C25 C24 121.50(13) . . ? C26 C25 H25 119.3 . . ? C24 C25 H25 119.3 . . ? C21 C26 C25 117.50(12) . . ? C21 C26 C29 121.00(12) . . ? C25 C26 C29 121.49(13) . . ? C22 C27 H27A 109.5 . . ? C22 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C22 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C24 C28 H28A 109.5 . . ? C24 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C24 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C26 C29 H29A 109.5 . . ? C26 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C26 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C36 C31 C32 120.6(3) . . ? C36 C31 H31 119.7 . . ? C32 C31 H31 119.7 . . ? C31 C32 C33 119.2(2) . . ? C31 C32 H32 120.4 . . ? C33 C32 H32 120.4 . . ? C34 C33 C32 118.5(2) . . ? C34 C33 H33 120.7 . . ? C32 C33 H33 120.7 . . ? C35 C34 C33 119.4(2) . . ? C35 C34 H34 120.3 . . ? C33 C34 H34 120.3 . . ? C34 C35 C36 120.6(2) . . ? C34 C35 H35 119.7 . . ? C36 C35 H35 119.7 . . ? C31 C36 C35 121.6(2) . . ? C31 C36 H36 119.2 . . ? C35 C36 H36 119.2 . . ? C1 N1 C3 110.43(11) . . ? C1 N1 C11 124.21(11) . . ? C3 N1 C11 125.32(11) . . ? C1 N2 C2 110.06(11) . . ? C1 N2 C21 124.45(11) . . ? C2 N2 C21 125.48(11) . . ? C3 N3 C4 113.90(11) . . ? data_complex_7 _database_code_depnum_ccdc_archive 'CCDC 859206' #TrackingRef '- all_compounds.cif' _audit_creation_date 2011-12-14T14:16:07-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C128 H172 Cl4 N12 O Rh4' _chemical_formula_moiety '4(C32 H43 Cl N3 Rh), O' _chemical_formula_weight 2448.22 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 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 34.4570(10) _cell_length_b 10.9240(3) _cell_length_c 32.2640(8) _cell_angle_alpha 90 _cell_angle_beta 96.3490(10) _cell_angle_gamma 90 _cell_volume 12070.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9954 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 30.40 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_diffrn 1.338 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 5088 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.679 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; 'SADABS, Sheldrick, Bruker, 2000' ; _exptl_absorpt_correction_T_min 0.693 _exptl_absorpt_correction_T_max 0.746 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device_type 'Bruker APEX II' _diffrn_measurement_method 'phi and omega scans' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% 0 _diffrn_reflns_av_R_equivalents 0.0333 _diffrn_reflns_av_unetI/netI 0.0253 _diffrn_reflns_number 78113 _diffrn_reflns_limit_h_min -42 _diffrn_reflns_limit_h_max 42 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 1 _diffrn_measured_fraction_theta_max 1 _reflns_number_total 12346 _reflns_number_gt 10668 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_solution 'SIR2004 (Giacovazzo et al, 2004)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # 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^ > 2\s(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^)+(0.0269P)^2^+31.6304P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment riding _refine_ls_extinction_method none _refine_ls_number_reflns 12346 _refine_ls_number_parameters 722 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.0471 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.0835 _refine_ls_wR_factor_gt 0.0799 _refine_ls_goodness_of_fit_ref 1.136 _refine_ls_restrained_S_all 1.136 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.693 _refine_diff_density_min -0.555 _refine_diff_density_rms 0.066 #----------------------------------------------------------------------------# # 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Rh Rh -1.1178 0.9187 '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' 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 C1A C 0.60007(8) 0.2724(2) 0.30401(8) 0.0258(6) Uani 1 1 d . . . C1B C 0.67739(8) 0.0266(2) 0.08251(8) 0.0237(6) Uani 1 1 d . . . C2A C 0.58363(9) 0.1002(3) 0.26578(8) 0.0291(6) Uani 1 1 d . . . C2B C 0.70657(8) -0.1555(3) 0.06969(9) 0.0293(6) Uani 1 1 d . . . C3A C 0.60527(9) 0.1703(3) 0.24305(9) 0.0304(6) Uani 1 1 d . . . H3A H 0.6125 0.1526 0.2168 0.036 Uiso 1 1 calc R . . C3B C 0.73350(8) -0.0863(3) 0.09192(9) 0.0299(6) Uani 1 1 d . . . H3B H 0.7593 -0.1076 0.1006 0.036 Uiso 1 1 calc R . . C4A C 0.57159(10) -0.0777(3) 0.22038(9) 0.0364(7) Uani 1 1 d . . . H4A H 0.5702 -0.0202 0.197 0.044 Uiso 1 1 calc R . . C4B C 0.74419(9) -0.3395(3) 0.05747(11) 0.0405(8) Uani 1 1 d . . . H4B H 0.7649 -0.2847 0.0502 0.049 Uiso 1 1 calc R . . C5A C 0.61186(11) -0.1350(3) 0.22495(11) 0.0496(9) Uani 1 1 d . . . H5A1 H 0.631 -0.0736 0.2334 0.074 Uiso 1 1 calc R . . H5A2 H 0.6171 -0.1693 0.1987 0.074 Uiso 1 1 calc R . . H5A3 H 0.613 -0.1986 0.2456 0.074 Uiso 1 1 calc R . . C5B C 0.75457(11) -0.3850(3) 0.10126(13) 0.0539(10) Uani 1 1 d . . . H5B1 H 0.7534 -0.3183 0.1205 0.081 Uiso 1 1 calc R . . H5B2 H 0.7805 -0.4183 0.104 0.081 Uiso 1 1 calc R . . H5B3 H 0.7364 -0.4474 0.1073 0.081 Uiso 1 1 calc R . . C6A C 0.53965(13) -0.1714(4) 0.21105(13) 0.0663(12) Uani 1 1 d . . . H6A1 H 0.5405 -0.229 0.2336 0.099 Uiso 1 1 calc R . . H6A2 H 0.5434 -0.2138 0.1857 0.099 Uiso 1 1 calc R . . H6A3 H 0.5148 -0.131 0.2079 0.099 Uiso 1 1 calc R . . C6B C 0.73974(12) -0.4444(3) 0.02621(13) 0.0601(11) Uani 1 1 d . . . H6B1 H 0.7184 -0.4957 0.032 0.09 Uiso 1 1 calc R . . H6B2 H 0.7634 -0.4917 0.0284 0.09 Uiso 1 1 calc R . . H6B3 H 0.7347 -0.4119 -0.0015 0.09 Uiso 1 1 calc R . . C11A C 0.56251(8) 0.1082(2) 0.33649(8) 0.0238(6) Uani 1 1 d . . . C11B C 0.63605(8) -0.1336(2) 0.04388(8) 0.0256(6) Uani 1 1 d . . . C12A C 0.58370(8) 0.0224(2) 0.36166(9) 0.0264(6) Uani 1 1 d . . . C12B C 0.61413(9) -0.2108(3) 0.06629(9) 0.0303(6) Uani 1 1 d . . . C13A C 0.56509(9) -0.0339(3) 0.39251(9) 0.0325(7) Uani 1 1 d . . . H13A H 0.5788 -0.0912 0.4097 0.039 Uiso 1 1 calc R . . C13B C 0.57943(9) -0.2561(3) 0.04648(10) 0.0355(7) Uani 1 1 d . . . H13B H 0.5641 -0.3063 0.0613 0.043 Uiso 1 1 calc R . . C14A C 0.52692(9) -0.0082(3) 0.39869(9) 0.0354(7) Uani 1 1 d . . . C14B C 0.56672(9) -0.2289(3) 0.00508(10) 0.0369(7) Uani 1 1 d . . . C15A C 0.50690(9) 0.0753(3) 0.37249(9) 0.0368(7) Uani 1 1 d . . . H15A H 0.4811 0.0933 0.3763 0.044 Uiso 1 1 calc R . . C15B C 0.59006(9) -0.1556(3) -0.01632(9) 0.0387(7) Uani 1 1 d . . . H15B H 0.5822 -0.138 -0.0442 0.046 Uiso 1 1 calc R . . C16A C 0.52367(8) 0.1335(3) 0.34065(9) 0.0296(6) Uani 1 1 d . . . C16B C 0.62503(9) -0.1067(3) 0.00209(8) 0.0310(6) Uani 1 1 d . . . C17A C 0.62493(8) -0.0099(3) 0.35483(10) 0.0345(7) Uani 1 1 d . . . H17A H 0.6363 -0.0598 0.3775 0.052 Uiso 1 1 calc R . . H17B H 0.64 0.0637 0.3535 0.052 Uiso 1 1 calc R . . H17C H 0.6249 -0.0542 0.3291 0.052 Uiso 1 1 calc R . . C17B C 0.62782(10) -0.2465(3) 0.11046(9) 0.0415(8) Uani 1 1 d . . . H17D H 0.6486 -0.305 0.1106 0.062 Uiso 1 1 calc R . . H17E H 0.6065 -0.2822 0.1231 0.062 Uiso 1 1 calc R . . H17F H 0.637 -0.1752 0.1259 0.062 Uiso 1 1 calc R . . C18A C 0.50778(11) -0.0691(4) 0.43297(12) 0.0561(10) Uani 1 1 d . . . H18A H 0.518 -0.035 0.4594 0.084 Uiso 1 1 calc R . . H18B H 0.5131 -0.1554 0.4329 0.084 Uiso 1 1 calc R . . H18C H 0.4801 -0.0558 0.4286 0.084 Uiso 1 1 calc R . . C18B C 0.52879(10) -0.2795(4) -0.01550(12) 0.0555(10) Uani 1 1 d . . . H18D H 0.5074 -0.2376 -0.005 0.083 Uiso 1 1 calc R . . H18E H 0.5273 -0.3653 -0.0095 0.083 Uiso 1 1 calc R . . H18F H 0.5275 -0.2678 -0.0451 0.083 Uiso 1 1 calc R . . C19A C 0.49948(10) 0.2179(4) 0.31172(11) 0.0510(9) Uani 1 1 d . . . H19A H 0.5132 0.2361 0.2881 0.077 Uiso 1 1 calc R . . H19B H 0.4947 0.2924 0.3261 0.077 Uiso 1 1 calc R . . H19C H 0.475 0.1793 0.3024 0.077 Uiso 1 1 calc R . . C19B C 0.65005(10) -0.0321(3) -0.02333(9) 0.0421(8) Uani 1 1 d . . . H19D H 0.6753 -0.0209 -0.008 0.063 Uiso 1 1 calc R . . H19E H 0.6381 0.0462 -0.0292 0.063 Uiso 1 1 calc R . . H19F H 0.6528 -0.0739 -0.049 0.063 Uiso 1 1 calc R . . C21A C 0.63789(8) 0.3726(2) 0.25191(8) 0.0269(6) Uani 1 1 d . . . C21B C 0.73411(8) 0.1211(3) 0.12421(9) 0.0270(6) Uani 1 1 d . . . C22A C 0.67604(8) 0.3902(3) 0.26984(8) 0.0288(6) Uani 1 1 d . . . C22B C 0.72347(8) 0.1407(3) 0.16417(8) 0.0278(6) Uani 1 1 d . . . C23A C 0.69668(9) 0.4870(3) 0.25513(9) 0.0343(7) Uani 1 1 d . . . H23A H 0.7221 0.5014 0.2671 0.041 Uiso 1 1 calc R . . C23B C 0.74068(8) 0.2384(3) 0.18654(9) 0.0320(7) Uani 1 1 d . . . H23B H 0.7332 0.2553 0.2128 0.038 Uiso 1 1 calc R . . C24A C 0.68105(9) 0.5630(3) 0.22336(9) 0.0330(7) Uani 1 1 d . . . C24B C 0.76858(8) 0.3120(3) 0.17127(9) 0.0337(7) Uani 1 1 d . . . C25A C 0.64337(9) 0.5396(3) 0.20551(9) 0.0362(7) Uani 1 1 d . . . H25A H 0.6328 0.5883 0.1835 0.043 Uiso 1 1 calc R . . C25B C 0.77913(9) 0.2858(3) 0.13199(10) 0.0359(7) Uani 1 1 d . . . H25B H 0.7982 0.3335 0.1216 0.043 Uiso 1 1 calc R . . C26A C 0.62096(9) 0.4460(3) 0.21937(9) 0.0346(7) Uani 1 1 d . . . C26B C 0.76239(8) 0.1918(3) 0.10785(9) 0.0325(7) Uani 1 1 d . . . C27A C 0.69481(9) 0.3075(3) 0.30305(11) 0.0436(8) Uani 1 1 d . . . H27A H 0.7224 0.3227 0.307 0.065 Uiso 1 1 calc R . . H27B H 0.6902 0.2238 0.2949 0.065 Uiso 1 1 calc R . . H27C H 0.6839 0.3227 0.3287 0.065 Uiso 1 1 calc R . . C27B C 0.69493(9) 0.0592(3) 0.18279(9) 0.0385(7) Uani 1 1 d . . . H27D H 0.6953 0.077 0.212 0.058 Uiso 1 1 calc R . . H27E H 0.702 -0.0248 0.1793 0.058 Uiso 1 1 calc R . . H27F H 0.6692 0.0733 0.169 0.058 Uiso 1 1 calc R . . C28A C 0.70384(10) 0.6675(3) 0.20791(11) 0.0489(9) Uani 1 1 d . . . H28A H 0.7309 0.6588 0.2183 0.073 Uiso 1 1 calc R . . H28B H 0.6941 0.7434 0.2176 0.073 Uiso 1 1 calc R . . H28C H 0.7011 0.6671 0.178 0.073 Uiso 1 1 calc R . . C28B C 0.78692(10) 0.4168(3) 0.19669(11) 0.0488(9) Uani 1 1 d . . . H28D H 0.812 0.3921 0.21 0.073 Uiso 1 1 calc R . . H28E H 0.7704 0.4397 0.2175 0.073 Uiso 1 1 calc R . . H28F H 0.7901 0.4853 0.1787 0.073 Uiso 1 1 calc R . . C29A C 0.57956(10) 0.4279(4) 0.20034(11) 0.0544(10) Uani 1 1 d . . . H29A H 0.5709 0.4993 0.1847 0.082 Uiso 1 1 calc R . . H29B H 0.5631 0.4145 0.222 0.082 Uiso 1 1 calc R . . H29C H 0.5782 0.358 0.1822 0.082 Uiso 1 1 calc R . . C29B C 0.77326(10) 0.1705(4) 0.06435(10) 0.0483(9) Uani 1 1 d . . . H29D H 0.7887 0.2379 0.0564 0.072 Uiso 1 1 calc R . . H29E H 0.75 0.1641 0.0452 0.072 Uiso 1 1 calc R . . H29F H 0.788 0.0961 0.0638 0.072 Uiso 1 1 calc R . . C31A C 0.61336(9) 0.5421(3) 0.39837(11) 0.0516(10) Uani 1 1 d D . . C31B C 0.58992(9) 0.3032(3) 0.08154(12) 0.0409(8) Uani 1 1 d D . . C32A C 0.61213(18) 0.6648(4) 0.37767(14) 0.0865(17) Uani 1 1 d . . . H32A H 0.5912 0.7122 0.3876 0.104 Uiso 1 1 calc R . . H32B H 0.6364 0.707 0.3864 0.104 Uiso 1 1 calc R . . C32B C 0.58034(8) 0.2308(3) 0.04745(11) 0.0441(8) Uani 1 1 d D . . C33A C 0.60644(17) 0.6624(3) 0.33284(12) 0.0734(14) Uani 1 1 d . . . H33A H 0.6316 0.6745 0.3226 0.088 Uiso 1 1 calc R . . H33B H 0.59 0.7313 0.3234 0.088 Uiso 1 1 calc R . . C33B C 0.58720(11) 0.2617(4) 0.00347(12) 0.0619(11) Uani 1 1 d . . . H33C H 0.5688 0.3246 -0.0069 0.074 Uiso 1 1 calc R . . H33D H 0.5819 0.1896 -0.0138 0.074 Uiso 1 1 calc R . . C34A C 0.58838(12) 0.5480(3) 0.31319(11) 0.0499(9) Uani 1 1 d D . . C34B C 0.62798(11) 0.3057(4) -0.00127(11) 0.0537(10) Uani 1 1 d . . . H34A H 0.6286 0.3942 0.0008 0.064 Uiso 1 1 calc R . . H34B H 0.6345 0.2835 -0.0288 0.064 Uiso 1 1 calc R . . C35A C 0.55377(11) 0.4961(4) 0.32164(12) 0.0564(11) Uani 1 1 d D . . C35B C 0.65850(8) 0.2526(3) 0.03125(10) 0.0360(7) Uani 1 1 d D . . C36B C 0.66956(7) 0.3073(3) 0.07036(10) 0.0344(7) Uani 1 1 d D . . C37B C 0.65249(10) 0.4214(3) 0.08689(13) 0.0484(9) Uani 1 1 d . . . H37C H 0.663 0.4918 0.0736 0.058 Uiso 1 1 calc R . . H37D H 0.6606 0.4271 0.1166 0.058 Uiso 1 1 calc R . . C38A C 0.58095(13) 0.4803(4) 0.40663(11) 0.0540(10) Uani 1 1 d D . . C38B C 0.60798(11) 0.4268(3) 0.07981(15) 0.0612(11) Uani 1 1 d . . . H38A H 0.5985 0.4787 0.1009 0.073 Uiso 1 1 calc R . . H38B H 0.6001 0.4632 0.0528 0.073 Uiso 1 1 calc R . . N1A N 0.58087(7) 0.1627(2) 0.30305(7) 0.0248(5) Uani 1 1 d . . . N1B N 0.67226(7) -0.0859(2) 0.06416(7) 0.0261(5) Uani 1 1 d . . . N2A N 0.61485(7) 0.2758(2) 0.26693(7) 0.0277(5) Uani 1 1 d . . . N2B N 0.71493(6) 0.0248(2) 0.09941(7) 0.0261(5) Uani 1 1 d . . . N3A N 0.56441(8) -0.0091(2) 0.25780(8) 0.0388(6) Uani 1 1 d D . . N3B N 0.70737(7) -0.2721(2) 0.05387(8) 0.0388(6) Uani 1 1 d D . . Cl1A Cl 0.64613(3) 0.27372(8) 0.39569(2) 0.0445(2) Uani 1 1 d . . . Cl1B Cl 0.59829(2) 0.04253(7) 0.12463(2) 0.03785(18) Uani 1 1 d . . . Rh1A Rh 0.601531(7) 0.39643(2) 0.351978(7) 0.02768(6) Uani 1 1 d . . . Rh1B Rh 0.633920(6) 0.156323(19) 0.079135(6) 0.02289(6) Uani 1 1 d . . . C36A C 0.52759(14) 0.5499(5) 0.35263(16) 0.0867(16) Uani 1 1 d . . . H36A H 0.527 0.6382 0.3494 0.104 Uiso 1 1 calc R . . H36B H 0.5012 0.5201 0.3454 0.104 Uiso 1 1 calc R . . C37A C 0.53957(16) 0.5212(6) 0.39597(15) 0.102(2) Uani 1 1 d . . . H37A H 0.5225 0.4573 0.4044 0.123 Uiso 1 1 calc R . . H37B H 0.5354 0.5932 0.4125 0.123 Uiso 1 1 calc R . . O1 O 0.34656(14) 0.3800(4) 0.01251(13) 0.0445(11) Uani 0.5 1 d P . . H35G H 0.6777(7) 0.201(2) 0.0199(9) 0.043 Uiso 1 1 d D . . H36G H 0.6962(3) 0.291(3) 0.0821(9) 0.041 Uiso 1 1 d D . . H34H H 0.5944(10) 0.531(3) 0.2851(4) 0.06 Uiso 1 1 d D . . H32G H 0.5618(8) 0.167(2) 0.0519(11) 0.053 Uiso 1 1 d D . . H38H H 0.5864(11) 0.416(2) 0.4271(9) 0.065 Uiso 1 1 d D . . H3D H 0.6894(7) -0.289(3) 0.0322(7) 0.046 Uiso 1 1 d D . . H31G H 0.5793(9) 0.281(3) 0.1071(6) 0.049 Uiso 1 1 d D . . H35H H 0.5395(10) 0.448(3) 0.2996(9) 0.068 Uiso 1 1 d D . . H31H H 0.6389(5) 0.514(3) 0.4102(11) 0.062 Uiso 1 1 d D . . H3H H 0.5569(9) -0.052(3) 0.2793(7) 0.046 Uiso 1 1 d 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 C1A 0.0309(15) 0.0219(14) 0.0245(13) 0.0011(11) 0.0026(11) 0.0002(12) C1B 0.0256(14) 0.0248(14) 0.0210(13) -0.0008(11) 0.0034(10) 0.0003(11) C2A 0.0371(16) 0.0258(15) 0.0251(14) -0.0057(12) 0.0073(12) -0.0032(13) C2B 0.0317(15) 0.0259(15) 0.0299(14) -0.0017(12) 0.0014(12) 0.0071(12) C3A 0.0398(17) 0.0279(15) 0.0247(14) -0.0045(12) 0.0094(12) -0.0058(13) C3B 0.0272(15) 0.0280(15) 0.0336(15) -0.0037(12) -0.0004(12) 0.0079(12) C4A 0.052(2) 0.0317(17) 0.0276(15) -0.0099(12) 0.0126(14) -0.0082(14) C4B 0.0365(17) 0.0274(16) 0.061(2) 0.0004(15) 0.0204(15) 0.0040(14) C5A 0.068(2) 0.041(2) 0.0426(19) -0.0037(16) 0.0166(17) 0.0086(18) C5B 0.042(2) 0.039(2) 0.078(3) 0.0124(19) -0.0051(18) 0.0020(16) C6A 0.078(3) 0.056(3) 0.068(3) -0.032(2) 0.023(2) -0.031(2) C6B 0.073(3) 0.038(2) 0.076(3) -0.0101(19) 0.041(2) 0.0068(19) C11A 0.0294(14) 0.0218(14) 0.0208(13) -0.0036(11) 0.0056(11) -0.0027(11) C11B 0.0286(14) 0.0208(14) 0.0269(14) -0.0044(11) 0.0010(11) 0.0045(11) C12A 0.0261(14) 0.0226(14) 0.0308(14) -0.0022(11) 0.0052(11) 0.0008(11) C12B 0.0359(16) 0.0256(15) 0.0289(15) -0.0067(12) 0.0016(12) 0.0018(13) C13A 0.0345(16) 0.0305(16) 0.0325(15) 0.0075(13) 0.0039(12) 0.0010(13) C13B 0.0366(17) 0.0299(16) 0.0412(17) -0.0040(13) 0.0100(14) -0.0025(13) C14A 0.0333(17) 0.0431(19) 0.0310(15) 0.0015(14) 0.0090(13) -0.0076(14) C14B 0.0282(16) 0.0395(18) 0.0421(18) -0.0125(14) 0.0006(13) 0.0028(13) C15A 0.0220(14) 0.052(2) 0.0369(16) -0.0007(15) 0.0064(12) 0.0010(14) C15B 0.0358(17) 0.049(2) 0.0293(15) -0.0056(14) -0.0041(13) 0.0055(15) C16A 0.0264(14) 0.0352(17) 0.0266(14) -0.0021(12) -0.0002(11) 0.0016(12) C16B 0.0331(16) 0.0360(17) 0.0240(14) -0.0026(12) 0.0032(12) 0.0046(13) C17A 0.0307(16) 0.0267(16) 0.0475(18) 0.0029(13) 0.0101(13) 0.0045(12) C17B 0.059(2) 0.0336(18) 0.0311(16) 0.0044(13) 0.0008(15) -0.0047(15) C18A 0.049(2) 0.070(3) 0.052(2) 0.021(2) 0.0210(18) -0.0046(19) C18B 0.0359(19) 0.069(3) 0.060(2) -0.019(2) 0.0014(17) -0.0064(18) C19A 0.0346(18) 0.071(3) 0.046(2) 0.0137(18) -0.0004(15) 0.0121(18) C19B 0.0439(19) 0.057(2) 0.0258(15) -0.0015(15) 0.0040(13) -0.0041(16) C21A 0.0330(15) 0.0222(14) 0.0260(14) 0.0003(11) 0.0054(11) -0.0061(11) C21B 0.0241(14) 0.0281(15) 0.0279(14) -0.0029(12) -0.0013(11) 0.0020(11) C22A 0.0310(15) 0.0305(15) 0.0253(14) -0.0006(12) 0.0052(11) 0.0025(12) C22B 0.0233(14) 0.0330(16) 0.0261(14) 0.0028(12) -0.0015(11) 0.0018(12) C23A 0.0254(15) 0.0421(18) 0.0354(16) -0.0016(14) 0.0032(12) -0.0060(13) C23B 0.0302(15) 0.0392(17) 0.0260(14) -0.0045(13) -0.0002(12) 0.0003(13) C24A 0.0348(16) 0.0301(16) 0.0342(16) 0.0001(13) 0.0045(13) -0.0082(13) C24B 0.0277(15) 0.0356(17) 0.0365(16) -0.0033(13) -0.0023(12) -0.0003(13) C25A 0.0446(18) 0.0352(17) 0.0269(15) 0.0071(13) -0.0039(13) -0.0072(14) C25B 0.0264(15) 0.0394(18) 0.0419(17) 0.0013(14) 0.0034(13) -0.0075(13) C26A 0.0352(17) 0.0356(17) 0.0316(15) 0.0047(13) -0.0028(13) -0.0083(13) C26B 0.0244(15) 0.0413(18) 0.0319(15) -0.0027(13) 0.0040(12) -0.0001(13) C27A 0.0326(17) 0.051(2) 0.0475(19) 0.0153(16) 0.0052(14) 0.0086(15) C27B 0.0391(18) 0.049(2) 0.0268(15) 0.0014(14) 0.0024(13) -0.0083(15) C28A 0.049(2) 0.045(2) 0.053(2) 0.0104(17) 0.0081(17) -0.0163(17) C28B 0.043(2) 0.052(2) 0.050(2) -0.0094(17) 0.0018(16) -0.0123(17) C29A 0.046(2) 0.062(2) 0.050(2) 0.0192(18) -0.0154(17) -0.0196(18) C29B 0.0400(19) 0.068(3) 0.0387(18) -0.0097(17) 0.0143(15) -0.0133(17) C31A 0.088(3) 0.0296(18) 0.0338(18) -0.0105(14) -0.0072(18) 0.0014(19) C31B 0.0296(17) 0.0332(18) 0.061(2) 0.0045(16) 0.0118(15) 0.0092(14) C32A 0.148(5) 0.039(2) 0.064(3) 0.000(2) -0.027(3) -0.021(3) C32B 0.0271(17) 0.046(2) 0.057(2) 0.0133(17) -0.0058(15) 0.0037(14) C33A 0.146(5) 0.0265(19) 0.047(2) 0.0009(17) 0.010(3) -0.011(2) C33B 0.052(2) 0.079(3) 0.050(2) 0.020(2) -0.0169(18) 0.006(2) C34A 0.084(3) 0.0286(18) 0.0343(18) -0.0011(14) -0.0065(18) 0.0096(18) C34B 0.064(2) 0.059(2) 0.0378(19) 0.0201(17) 0.0019(17) 0.0016(19) C35A 0.061(3) 0.052(2) 0.051(2) -0.0184(18) -0.0171(19) 0.022(2) C35B 0.0400(18) 0.0355(18) 0.0345(16) 0.0120(14) 0.0136(14) 0.0024(14) C36B 0.0302(16) 0.0284(16) 0.0445(18) 0.0060(13) 0.0032(13) -0.0024(13) C37B 0.049(2) 0.0253(17) 0.071(2) -0.0032(16) 0.0071(18) -0.0054(15) C38A 0.079(3) 0.056(2) 0.0303(18) -0.0036(16) 0.0185(18) 0.016(2) C38B 0.058(2) 0.036(2) 0.093(3) -0.001(2) 0.021(2) 0.0079(18) N1A 0.0319(13) 0.0206(12) 0.0229(11) -0.0022(9) 0.0072(9) -0.0010(10) N1B 0.0297(12) 0.0237(12) 0.0240(11) -0.0015(9) -0.0014(9) 0.0040(10) N2A 0.0341(13) 0.0234(12) 0.0260(12) -0.0011(10) 0.0048(10) -0.0053(10) N2B 0.0252(12) 0.0263(12) 0.0262(12) -0.0017(10) 0.0001(9) 0.0019(10) N3A 0.0560(17) 0.0296(14) 0.0345(14) -0.0105(11) 0.0216(13) -0.0146(12) N3B 0.0388(15) 0.0319(14) 0.0432(15) -0.0119(12) -0.0063(12) 0.0103(12) Cl1A 0.0648(6) 0.0389(4) 0.0287(4) 0.0022(3) 0.0000(4) 0.0124(4) Cl1B 0.0294(4) 0.0450(5) 0.0409(4) 0.0139(3) 0.0116(3) 0.0016(3) Rh1A 0.03669(13) 0.02142(12) 0.02497(11) -0.00333(9) 0.00348(9) -0.00184(9) Rh1B 0.02259(11) 0.02286(11) 0.02333(11) 0.00199(8) 0.00297(8) 0.00235(9) C36A 0.062(3) 0.094(4) 0.100(4) -0.040(3) -0.006(3) 0.032(3) C37A 0.101(4) 0.146(5) 0.068(3) 0.028(3) 0.048(3) 0.069(4) O1 0.065(3) 0.035(2) 0.030(2) -0.0080(19) -0.014(2) 0.006(2) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C1A N2A 1.352(3) . ? C1A N1A 1.368(3) . ? C1A Rh1A 2.054(3) . ? C1B N2B 1.347(3) . ? C1B N1B 1.367(3) . ? C1B Rh1B 2.056(3) . ? C2A C3A 1.342(4) . ? C2A N3A 1.375(4) . ? C2A N1A 1.395(3) . ? C2B C3B 1.342(4) . ? C2B N3B 1.373(4) . ? C2B N1B 1.400(3) . ? C3A N2A 1.405(4) . ? C3A H3A 0.93 . ? C3B N2B 1.406(4) . ? C3B H3B 0.93 . ? C4A N3A 1.466(4) . ? C4A C6A 1.509(5) . ? C4A C5A 1.515(5) . ? C4A H4A 0.98 . ? C4B N3B 1.460(4) . ? C4B C5B 1.503(5) . ? C4B C6B 1.523(5) . ? C4B H4B 0.98 . ? C5A H5A1 0.96 . ? C5A H5A2 0.96 . ? C5A H5A3 0.96 . ? C5B H5B1 0.96 . ? C5B H5B2 0.96 . ? C5B H5B3 0.96 . ? C6A H6A1 0.96 . ? C6A H6A2 0.96 . ? C6A H6A3 0.96 . ? C6B H6B1 0.96 . ? C6B H6B2 0.96 . ? C6B H6B3 0.96 . ? C11A C16A 1.388(4) . ? C11A C12A 1.393(4) . ? C11A N1A 1.438(3) . ? C11B C12B 1.387(4) . ? C11B C16B 1.391(4) . ? C11B N1B 1.441(3) . ? C12A C13A 1.386(4) . ? C12A C17A 1.504(4) . ? C12B C13B 1.383(4) . ? C12B C17B 1.502(4) . ? C13A C14A 1.381(4) . ? C13A H13A 0.93 . ? C13B C14B 1.391(4) . ? C13B H13B 0.93 . ? C14A C15A 1.376(4) . ? C14A C18A 1.504(4) . ? C14B C15B 1.374(5) . ? C14B C18B 1.504(4) . ? C15A C16A 1.388(4) . ? C15A H15A 0.93 . ? C15B C16B 1.390(4) . ? C15B H15B 0.93 . ? C16A C19A 1.498(4) . ? C16B C19B 1.495(4) . ? C17A H17A 0.96 . ? C17A H17B 0.96 . ? C17A H17C 0.96 . ? C17B H17D 0.96 . ? C17B H17E 0.96 . ? C17B H17F 0.96 . ? C18A H18A 0.96 . ? C18A H18B 0.96 . ? C18A H18C 0.96 . ? C18B H18D 0.96 . ? C18B H18E 0.96 . ? C18B H18F 0.96 . ? C19A H19A 0.96 . ? C19A H19B 0.96 . ? C19A H19C 0.96 . ? C19B H19D 0.96 . ? C19B H19E 0.96 . ? C19B H19F 0.96 . ? C21A C22A 1.390(4) . ? C21A C26A 1.397(4) . ? C21A N2A 1.438(3) . ? C21B C26B 1.392(4) . ? C21B C22B 1.395(4) . ? C21B N2B 1.438(3) . ? C22A C23A 1.388(4) . ? C22A C27A 1.493(4) . ? C22B C23B 1.384(4) . ? C22B C27B 1.501(4) . ? C23A C24A 1.381(4) . ? C23A H23A 0.93 . ? C23B C24B 1.385(4) . ? C23B H23B 0.93 . ? C24A C25A 1.385(4) . ? C24A C28A 1.501(4) . ? C24B C25B 1.386(4) . ? C24B C28B 1.506(4) . ? C25A C26A 1.385(4) . ? C25A H25A 0.93 . ? C25B C26B 1.376(4) . ? C25B H25B 0.93 . ? C26A C29A 1.503(4) . ? C26B C29B 1.510(4) . ? C27A H27A 0.96 . ? C27A H27B 0.96 . ? C27A H27C 0.96 . ? C27B H27D 0.96 . ? C27B H27E 0.96 . ? C27B H27F 0.96 . ? C28A H28A 0.96 . ? C28A H28B 0.96 . ? C28A H28C 0.96 . ? C28B H28D 0.96 . ? C28B H28E 0.96 . ? C28B H28F 0.96 . ? C29A H29A 0.96 . ? C29A H29B 0.96 . ? C29A H29C 0.96 . ? C29B H29D 0.96 . ? C29B H29E 0.96 . ? C29B H29F 0.96 . ? C31A C38A 1.357(5) . ? C31A C32A 1.495(5) . ? C31A Rh1A 2.192(3) . ? C31A H31H 0.9700(2) . ? C31B C32B 1.365(5) . ? C31B C38B 1.490(5) . ? C31B Rh1B 2.215(3) . ? C31B H31G 0.97000(14) . ? C32A C33A 1.438(6) . ? C32A H32A 0.97 . ? C32A H32B 0.97 . ? C32B C33B 1.502(5) . ? C32B Rh1B 2.168(3) . ? C32B H32G 0.97000(15) . ? C33A C34A 1.505(5) . ? C33A H33A 0.97 . ? C33A H33B 0.97 . ? C33B C34B 1.509(5) . ? C33B H33C 0.97 . ? C33B H33D 0.97 . ? C34A C35A 1.375(6) . ? C34A Rh1A 2.095(3) . ? C34A H34H 0.97000(19) . ? C34B C35B 1.516(4) . ? C34B H34A 0.97 . ? C34B H34B 0.97 . ? C35A C36A 1.536(6) . ? C35A Rh1A 2.120(3) . ? C35A H35H 0.97000(13) . ? C35B C36B 1.410(4) . ? C35B Rh1B 2.121(3) . ? C35B H35G 0.97000(13) . ? C36B C37B 1.501(4) . ? C36B Rh1B 2.094(3) . ? C36B H36G 0.97000(17) . ? C37B C38B 1.526(5) . ? C37B H37C 0.97 . ? C37B H37D 0.97 . ? C38A C37A 1.497(6) . ? C38A Rh1A 2.174(3) . ? C38A H38H 0.97000(16) . ? C38B H38A 0.97 . ? C38B H38B 0.97 . ? N3A H3H 0.90000(14) . ? N3B H3D 0.90000(11) . ? Cl1A Rh1A 2.3807(8) . ? Cl1B Rh1B 2.3677(7) . ? C36A C37A 1.448(6) . ? C36A H36A 0.97 . ? C36A H36B 0.97 . ? C37A H37A 0.97 . ? C37A H37B 0.97 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2A C1A N1A 103.5(2) . . ? N2A C1A Rh1A 132.0(2) . . ? N1A C1A Rh1A 124.54(19) . . ? N2B C1B N1B 103.6(2) . . ? N2B C1B Rh1B 133.8(2) . . ? N1B C1B Rh1B 122.56(19) . . ? C3A C2A N3A 132.7(3) . . ? C3A C2A N1A 106.7(2) . . ? N3A C2A N1A 120.6(2) . . ? C3B C2B N3B 132.8(3) . . ? C3B C2B N1B 106.6(2) . . ? N3B C2B N1B 120.5(2) . . ? C2A C3A N2A 106.2(2) . . ? C2A C3A H3A 126.9 . . ? N2A C3A H3A 126.9 . . ? C2B C3B N2B 106.1(2) . . ? C2B C3B H3B 126.9 . . ? N2B C3B H3B 126.9 . . ? N3A C4A C6A 109.0(3) . . ? N3A C4A C5A 111.6(3) . . ? C6A C4A C5A 112.3(3) . . ? N3A C4A H4A 107.9 . . ? C6A C4A H4A 107.9 . . ? C5A C4A H4A 107.9 . . ? N3B C4B C5B 110.8(3) . . ? N3B C4B C6B 107.7(3) . . ? C5B C4B C6B 111.7(3) . . ? N3B C4B H4B 108.9 . . ? C5B C4B H4B 108.9 . . ? C6B C4B H4B 108.9 . . ? C4A C5A H5A1 109.5 . . ? C4A C5A H5A2 109.5 . . ? H5A1 C5A H5A2 109.5 . . ? C4A C5A H5A3 109.5 . . ? H5A1 C5A H5A3 109.5 . . ? H5A2 C5A H5A3 109.5 . . ? C4B C5B H5B1 109.5 . . ? C4B C5B H5B2 109.5 . . ? H5B1 C5B H5B2 109.5 . . ? C4B C5B H5B3 109.5 . . ? H5B1 C5B H5B3 109.5 . . ? H5B2 C5B H5B3 109.5 . . ? C4A C6A H6A1 109.5 . . ? C4A C6A H6A2 109.5 . . ? H6A1 C6A H6A2 109.5 . . ? C4A C6A H6A3 109.5 . . ? H6A1 C6A H6A3 109.5 . . ? H6A2 C6A H6A3 109.5 . . ? C4B C6B H6B1 109.5 . . ? C4B C6B H6B2 109.5 . . ? H6B1 C6B H6B2 109.5 . . ? C4B C6B H6B3 109.5 . . ? H6B1 C6B H6B3 109.5 . . ? H6B2 C6B H6B3 109.5 . . ? C16A C11A C12A 121.8(3) . . ? C16A C11A N1A 119.9(2) . . ? C12A C11A N1A 118.0(2) . . ? C12B C11B C16B 121.8(3) . . ? C12B C11B N1B 118.5(2) . . ? C16B C11B N1B 119.6(3) . . ? C13A C12A C11A 117.6(3) . . ? C13A C12A C17A 121.4(3) . . ? C11A C12A C17A 121.0(2) . . ? C13B C12B C11B 118.0(3) . . ? C13B C12B C17B 120.7(3) . . ? C11B C12B C17B 121.3(3) . . ? C14A C13A C12A 122.5(3) . . ? C14A C13A H13A 118.8 . . ? C12A C13A H13A 118.8 . . ? C12B C13B C14B 122.1(3) . . ? C12B C13B H13B 118.9 . . ? C14B C13B H13B 118.9 . . ? C15A C14A C13A 117.8(3) . . ? C15A C14A C18A 121.0(3) . . ? C13A C14A C18A 121.2(3) . . ? C15B C14B C13B 117.9(3) . . ? C15B C14B C18B 121.4(3) . . ? C13B C14B C18B 120.8(3) . . ? C14A C15A C16A 122.5(3) . . ? C14A C15A H15A 118.8 . . ? C16A C15A H15A 118.8 . . ? C14B C15B C16B 122.5(3) . . ? C14B C15B H15B 118.8 . . ? C16B C15B H15B 118.8 . . ? C11A C16A C15A 117.7(3) . . ? C11A C16A C19A 122.6(3) . . ? C15A C16A C19A 119.7(3) . . ? C15B C16B C11B 117.6(3) . . ? C15B C16B C19B 120.0(3) . . ? C11B C16B C19B 122.3(3) . . ? C12A C17A H17A 109.5 . . ? C12A C17A H17B 109.5 . . ? H17A C17A H17B 109.5 . . ? C12A C17A H17C 109.5 . . ? H17A C17A H17C 109.5 . . ? H17B C17A H17C 109.5 . . ? C12B C17B H17D 109.5 . . ? C12B C17B H17E 109.5 . . ? H17D C17B H17E 109.5 . . ? C12B C17B H17F 109.5 . . ? H17D C17B H17F 109.5 . . ? H17E C17B H17F 109.5 . . ? C14A C18A H18A 109.5 . . ? C14A C18A H18B 109.5 . . ? H18A C18A H18B 109.5 . . ? C14A C18A H18C 109.5 . . ? H18A C18A H18C 109.5 . . ? H18B C18A H18C 109.5 . . ? C14B C18B H18D 109.5 . . ? C14B C18B H18E 109.5 . . ? H18D C18B H18E 109.5 . . ? C14B C18B H18F 109.5 . . ? H18D C18B H18F 109.5 . . ? H18E C18B H18F 109.5 . . ? C16A C19A H19A 109.5 . . ? C16A C19A H19B 109.5 . . ? H19A C19A H19B 109.5 . . ? C16A C19A H19C 109.5 . . ? H19A C19A H19C 109.5 . . ? H19B C19A H19C 109.5 . . ? C16B C19B H19D 109.5 . . ? C16B C19B H19E 109.5 . . ? H19D C19B H19E 109.5 . . ? C16B C19B H19F 109.5 . . ? H19D C19B H19F 109.5 . . ? H19E C19B H19F 109.5 . . ? C22A C21A C26A 122.0(3) . . ? C22A C21A N2A 119.6(2) . . ? C26A C21A N2A 118.4(2) . . ? C26B C21B C22B 122.1(3) . . ? C26B C21B N2B 119.5(2) . . ? C22B C21B N2B 118.4(2) . . ? C23A C22A C21A 117.4(3) . . ? C23A C22A C27A 120.6(3) . . ? C21A C22A C27A 122.0(3) . . ? C23B C22B C21B 117.3(3) . . ? C23B C22B C27B 120.7(3) . . ? C21B C22B C27B 122.0(3) . . ? C24A C23A C22A 122.6(3) . . ? C24A C23A H23A 118.7 . . ? C22A C23A H23A 118.7 . . ? C22B C23B C24B 122.4(3) . . ? C22B C23B H23B 118.8 . . ? C24B C23B H23B 118.8 . . ? C23A C24A C25A 117.9(3) . . ? C23A C24A C28A 121.9(3) . . ? C25A C24A C28A 120.2(3) . . ? C23B C24B C25B 117.9(3) . . ? C23B C24B C28B 120.9(3) . . ? C25B C24B C28B 121.2(3) . . ? C24A C25A C26A 122.2(3) . . ? C24A C25A H25A 118.9 . . ? C26A C25A H25A 118.9 . . ? C26B C25B C24B 122.4(3) . . ? C26B C25B H25B 118.8 . . ? C24B C25B H25B 118.8 . . ? C25A C26A C21A 117.7(3) . . ? C25A C26A C29A 120.2(3) . . ? C21A C26A C29A 122.0(3) . . ? C25B C26B C21B 117.8(3) . . ? C25B C26B C29B 120.6(3) . . ? C21B C26B C29B 121.5(3) . . ? C22A C27A H27A 109.5 . . ? C22A C27A H27B 109.5 . . ? H27A C27A H27B 109.5 . . ? C22A C27A H27C 109.5 . . ? H27A C27A H27C 109.5 . . ? H27B C27A H27C 109.5 . . ? C22B C27B H27D 109.5 . . ? C22B C27B H27E 109.5 . . ? H27D C27B H27E 109.5 . . ? C22B C27B H27F 109.5 . . ? H27D C27B H27F 109.5 . . ? H27E C27B H27F 109.5 . . ? C24A C28A H28A 109.5 . . ? C24A C28A H28B 109.5 . . ? H28A C28A H28B 109.5 . . ? C24A C28A H28C 109.5 . . ? H28A C28A H28C 109.5 . . ? H28B C28A H28C 109.5 . . ? C24B C28B H28D 109.5 . . ? C24B C28B H28E 109.5 . . ? H28D C28B H28E 109.5 . . ? C24B C28B H28F 109.5 . . ? H28D C28B H28F 109.5 . . ? H28E C28B H28F 109.5 . . ? C26A C29A H29A 109.5 . . ? C26A C29A H29B 109.5 . . ? H29A C29A H29B 109.5 . . ? C26A C29A H29C 109.5 . . ? H29A C29A H29C 109.5 . . ? H29B C29A H29C 109.5 . . ? C26B C29B H29D 109.5 . . ? C26B C29B H29E 109.5 . . ? H29D C29B H29E 109.5 . . ? C26B C29B H29F 109.5 . . ? H29D C29B H29F 109.5 . . ? H29E C29B H29F 109.5 . . ? C38A C31A C32A 123.4(4) . . ? C38A C31A Rh1A 71.2(2) . . ? C32A C31A Rh1A 110.6(2) . . ? C38A C31A H31H 119(2) . . ? C32A C31A H31H 116(2) . . ? Rh1A C31A H31H 97(2) . . ? C32B C31B C38B 124.0(3) . . ? C32B C31B Rh1B 69.98(18) . . ? C38B C31B Rh1B 111.4(2) . . ? C32B C31B H31G 117(2) . . ? C38B C31B H31G 117(2) . . ? Rh1B C31B H31G 100(2) . . ? C33A C32A C31A 115.3(3) . . ? C33A C32A H32A 108.4 . . ? C31A C32A H32A 108.4 . . ? C33A C32A H32B 108.5 . . ? C31A C32A H32B 108.5 . . ? H32A C32A H32B 107.5 . . ? C31B C32B C33B 125.6(3) . . ? C31B C32B Rh1B 73.75(18) . . ? C33B C32B Rh1B 108.4(2) . . ? C31B C32B H32G 114(2) . . ? C33B C32B H32G 118(2) . . ? Rh1B C32B H32G 102(2) . . ? C32A C33A C34A 116.3(3) . . ? C32A C33A H33A 108.2 . . ? C34A C33A H33A 108.2 . . ? C32A C33A H33B 108.2 . . ? C34A C33A H33B 108.2 . . ? H33A C33A H33B 107.4 . . ? C32B C33B C34B 114.4(3) . . ? C32B C33B H33C 108.7 . . ? C34B C33B H33C 108.7 . . ? C32B C33B H33D 108.7 . . ? C34B C33B H33D 108.7 . . ? H33C C33B H33D 107.6 . . ? C35A C34A C33A 125.9(4) . . ? C35A C34A Rh1A 72.0(2) . . ? C33A C34A Rh1A 110.7(2) . . ? C35A C34A H34H 113(2) . . ? C33A C34A H34H 116(2) . . ? Rh1A C34A H34H 111(2) . . ? C33B C34B C35B 113.0(3) . . ? C33B C34B H34A 109 . . ? C35B C34B H34A 109 . . ? C33B C34B H34B 109 . . ? C35B C34B H34B 109 . . ? H34A C34B H34B 107.8 . . ? C34A C35A C36A 123.8(4) . . ? C34A C35A Rh1A 70.0(2) . . ? C36A C35A Rh1A 112.2(3) . . ? C34A C35A H35H 117(2) . . ? C36A C35A H35H 113(2) . . ? Rh1A C35A H35H 111(2) . . ? C36B C35B C34B 123.7(3) . . ? C36B C35B Rh1B 69.41(16) . . ? C34B C35B Rh1B 113.0(2) . . ? C36B C35B H35G 117.1(19) . . ? C34B C35B H35G 114.2(19) . . ? Rh1B C35B H35G 109(2) . . ? C35B C36B C37B 126.3(3) . . ? C35B C36B Rh1B 71.52(17) . . ? C37B C36B Rh1B 110.3(2) . . ? C35B C36B H36G 114.8(19) . . ? C37B C36B H36G 114(2) . . ? Rh1B C36B H36G 110(2) . . ? C36B C37B C38B 113.9(3) . . ? C36B C37B H37C 108.8 . . ? C38B C37B H37C 108.8 . . ? C36B C37B H37D 108.8 . . ? C38B C37B H37D 108.8 . . ? H37C C37B H37D 107.7 . . ? C31A C38A C37A 126.1(4) . . ? C31A C38A Rh1A 72.6(2) . . ? C37A C38A Rh1A 109.1(3) . . ? C31A C38A H38H 113(2) . . ? C37A C38A H38H 119(2) . . ? Rh1A C38A H38H 101(2) . . ? C31B C38B C37B 112.1(3) . . ? C31B C38B H38A 109.2 . . ? C37B C38B H38A 109.2 . . ? C31B C38B H38B 109.2 . . ? C37B C38B H38B 109.2 . . ? H38A C38B H38B 107.9 . . ? C1A N1A C2A 111.7(2) . . ? C1A N1A C11A 126.7(2) . . ? C2A N1A C11A 121.5(2) . . ? C1B N1B C2B 111.5(2) . . ? C1B N1B C11B 125.9(2) . . ? C2B N1B C11B 122.5(2) . . ? C1A N2A C3A 112.0(2) . . ? C1A N2A C21A 126.5(2) . . ? C3A N2A C21A 121.6(2) . . ? C1B N2B C3B 112.2(2) . . ? C1B N2B C21B 125.2(2) . . ? C3B N2B C21B 122.5(2) . . ? C2A N3A C4A 118.5(2) . . ? C2A N3A H3H 119(2) . . ? C4A N3A H3H 117(2) . . ? C2B N3B C4B 119.4(3) . . ? C2B N3B H3D 116(2) . . ? C4B N3B H3D 118(2) . . ? C1A Rh1A C34A 94.92(12) . . ? C1A Rh1A C35A 92.17(12) . . ? C34A Rh1A C35A 38.08(16) . . ? C1A Rh1A C38A 154.97(14) . . ? C34A Rh1A C38A 94.77(14) . . ? C35A Rh1A C38A 81.49(15) . . ? C1A Rh1A C31A 168.82(12) . . ? C34A Rh1A C31A 81.11(13) . . ? C35A Rh1A C31A 91.07(13) . . ? C38A Rh1A C31A 36.20(14) . . ? C1A Rh1A Cl1A 92.02(8) . . ? C34A Rh1A Cl1A 151.86(12) . . ? C35A Rh1A Cl1A 168.46(13) . . ? C38A Rh1A Cl1A 90.22(11) . . ? C31A Rh1A Cl1A 86.86(9) . . ? C1B Rh1B C36B 96.62(11) . . ? C1B Rh1B C35B 91.90(11) . . ? C36B Rh1B C35B 39.07(12) . . ? C1B Rh1B C32B 149.45(13) . . ? C36B Rh1B C32B 97.02(12) . . ? C35B Rh1B C32B 81.85(12) . . ? C1B Rh1B C31B 174.26(12) . . ? C36B Rh1B C31B 81.26(11) . . ? C35B Rh1B C31B 89.78(12) . . ? C32B Rh1B C31B 36.28(13) . . ? C1B Rh1B Cl1B 91.71(8) . . ? C36B Rh1B Cl1B 148.15(9) . . ? C35B Rh1B Cl1B 171.12(8) . . ? C32B Rh1B Cl1B 90.95(9) . . ? C31B Rh1B Cl1B 87.41(9) . . ? C37A C36A C35A 114.8(4) . . ? C37A C36A H36A 108.6 . . ? C35A C36A H36A 108.6 . . ? C37A C36A H36B 108.6 . . ? C35A C36A H36B 108.6 . . ? H36A C36A H36B 107.5 . . ? C36A C37A C38A 116.7(4) . . ? C36A C37A H37A 108.1 . . ? C38A C37A H37A 108.1 . . ? C36A C37A H37B 108.1 . . ? C38A C37A H37B 108.1 . . ? H37A C37A H37B 107.3 . . ? _vrf_PLAT311_complex_7 ; PROBLEM: Isolated Disordered Oxygen Atom (No H's ?) ..... *O1 RESPONSE: In the final stages of the refinment, Fourier maps showed an isolated peak in the vicinity of N3b and Cl1a, which finally refined as 1/2 of an oxygen atom. It is attributed to a water molecule statistically located between these to atoms; the corresponding hydrogen atoms, however, could not be located in an unambiguous manner and were not included in the refinment. ; data_complex_8 _database_code_depnum_ccdc_archive 'CCDC 859207' #TrackingRef '- all_compounds.cif' _audit_creation_date 2010-04-21T08:50:29-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C32 H41 Cl N3 O Rh' _chemical_formula_moiety 'C32 H41 Cl N3 O Rh' _chemical_formula_weight 622.04 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.355(5) _cell_length_b 12.164(5) _cell_length_c 15.375(5) _cell_angle_alpha 87.110(5) _cell_angle_beta 86.360(5) _cell_angle_gamma 88.950(5) _cell_volume 1557.3(12) _cell_formula_units_Z 2 _cell_measurement_temperature 160(2) _cell_measurement_reflns_used 9999 _cell_measurement_theta_min 2.09 _cell_measurement_theta_max 40.62 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description parallelepiped _exptl_crystal_colour brown _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_meas_temp ? _exptl_crystal_density_diffrn 1.327 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.662 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; 'TWINABS (Bruker, V1.05) ; _exptl_absorpt_correction_T_min 0.854 _exptl_absorpt_correction_T_max 1.000 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 160(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device_type 'Bruker D8 Apex II' _diffrn_measurement_method \f _diffrn_radiation_source 'sealed tube' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% 0 _diffrn_reflns_av_R_equivalents 0.0 _diffrn_reflns_av_unetI/netI 0.0124 _diffrn_reflns_number 13874 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_full 26.37 _reflns_number_total 13874 _reflns_number_gt 12973 _reflns_threshold_expression >2sigma(I) _diffrn_measured_fraction_theta_max 0.984 _diffrn_measured_fraction_theta_full 0.984 #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' #----------------------------------------------------------------------------# # 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^)+(0.0813P)^2^+3.4843P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 13784 _refine_ls_number_parameters 364 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0407 _refine_ls_R_factor_gt 0.0361 _refine_ls_wR_factor_ref 0.1297 _refine_ls_wR_factor_gt 0.1214 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.661 _refine_diff_density_min -0.777 _refine_diff_density_rms 0.088 #----------------------------------------------------------------------------# # 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Rh Rh -1.1178 0.9187 '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' 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 C1 C 0.2628(3) 0.2325(2) 0.70533(16) 0.0168(5) Uani 1 1 d . . . C2 C 0.1673(3) 0.0783(2) 0.78853(17) 0.0182(5) Uani 1 1 d . . . C3 C 0.1812(3) 0.0504(2) 0.69275(17) 0.0182(5) Uani 1 1 d . . . C4 C 0.0610(4) -0.0885(3) 0.8571(2) 0.0312(7) Uani 1 1 d . . . H4 H 0.0645 -0.1124 0.7970 0.037 Uiso 1 1 calc R . . C5 C -0.1122(5) -0.0881(3) 0.8968(3) 0.0465(9) Uani 1 1 d . . . H5A H -0.1132 -0.0681 0.9564 0.070 Uiso 1 1 calc R . . H5B H -0.1562 -0.1601 0.8944 0.070 Uiso 1 1 calc R . . H5C H -0.1754 -0.0357 0.8644 0.070 Uiso 1 1 calc R . . C6 C 0.1704(5) -0.1632(3) 0.9127(3) 0.0453(9) Uani 1 1 d . . . H6A H 0.2784 -0.1605 0.8874 0.068 Uiso 1 1 calc R . . H6B H 0.1333 -0.2376 0.9142 0.068 Uiso 1 1 calc R . . H6C H 0.1674 -0.1381 0.9710 0.068 Uiso 1 1 calc R . . C11 C 0.1690(3) 0.4173(2) 0.57669(18) 0.0209(5) Uani 1 1 d D . . C12 C 0.0718(3) 0.4323(2) 0.65404(19) 0.0228(6) Uani 1 1 d D . . C13 C 0.0122(4) 0.5455(3) 0.6857(2) 0.0379(8) Uani 1 1 d . . . H13A H -0.0924 0.5370 0.7163 0.046 Uiso 1 1 calc R . . H13B H -0.0001 0.5956 0.6354 0.046 Uiso 1 1 calc R . . C14 C 0.1277(5) 0.5958(3) 0.7467(3) 0.0454(9) Uani 1 1 d . . . H14A H 0.1145 0.6753 0.7432 0.054 Uiso 1 1 calc R . . H14B H 0.0986 0.5704 0.8064 0.054 Uiso 1 1 calc R . . C15 C 0.3050(4) 0.5665(3) 0.7251(2) 0.0361(7) Uani 1 1 d D . . C16 C 0.3819(3) 0.5703(3) 0.6429(2) 0.0362(8) Uani 1 1 d D . . C17 C 0.3048(5) 0.6062(3) 0.5582(2) 0.0424(9) Uani 1 1 d . . . H17A H 0.3844 0.6425 0.5185 0.051 Uiso 1 1 calc R . . H17B H 0.2191 0.6590 0.5709 0.051 Uiso 1 1 calc R . . C18 C 0.2362(4) 0.5078(3) 0.5134(2) 0.0328(7) Uani 1 1 d . . . H18A H 0.1518 0.5348 0.4771 0.039 Uiso 1 1 calc R . . H18B H 0.3205 0.4764 0.4755 0.039 Uiso 1 1 calc R . . C21 C 0.2494(3) 0.2449(2) 0.86764(17) 0.0195(5) Uani 1 1 d . . . C22 C 0.3974(3) 0.2249(2) 0.90608(19) 0.0235(6) Uani 1 1 d . . . C23 C 0.4259(4) 0.2844(3) 0.97934(19) 0.0281(6) Uani 1 1 d . . . H23 H 0.5239 0.2748 1.0045 0.034 Uiso 1 1 calc R . . C24 C 0.3112(4) 0.3585(3) 1.01642(19) 0.0287(6) Uani 1 1 d . . . C25 C 0.1617(4) 0.3689(3) 0.9796(2) 0.0279(6) Uani 1 1 d . . . H25 H 0.0835 0.4148 1.0048 0.034 Uiso 1 1 calc R . . C26 C 0.1265(3) 0.3123(2) 0.90614(18) 0.0224(5) Uani 1 1 d . . . C27 C 0.5223(4) 0.1420(3) 0.8700(2) 0.0327(7) Uani 1 1 d . . . H27A H 0.6186 0.1463 0.9005 0.049 Uiso 1 1 calc R . . H27B H 0.5458 0.1589 0.8090 0.049 Uiso 1 1 calc R . . H27C H 0.4805 0.0689 0.8781 0.049 Uiso 1 1 calc R . . C28 C 0.3486(5) 0.4224(3) 1.0957(2) 0.0468(9) Uani 1 1 d . . . H28A H 0.3740 0.4970 1.0772 0.070 Uiso 1 1 calc R . . H28B H 0.4384 0.3884 1.1230 0.070 Uiso 1 1 calc R . . H28C H 0.2568 0.4220 1.1366 0.070 Uiso 1 1 calc R . . C29 C -0.0394(4) 0.3211(3) 0.8707(2) 0.0342(7) Uani 1 1 d . . . H29A H -0.1175 0.3361 0.9173 0.051 Uiso 1 1 calc R . . H29B H -0.0640 0.2531 0.8459 0.051 Uiso 1 1 calc R . . H29C H -0.0414 0.3798 0.8266 0.051 Uiso 1 1 calc R . . C31 C 0.2814(3) 0.1503(2) 0.55494(17) 0.0172(5) Uani 1 1 d . . . C32 C 0.4462(3) 0.1454(2) 0.52789(19) 0.0207(5) Uani 1 1 d . . . C33 C 0.4880(3) 0.1514(2) 0.4375(2) 0.0257(6) Uani 1 1 d . . . H33 H 0.5957 0.1497 0.4181 0.031 Uiso 1 1 calc R . . C34 C 0.3707(4) 0.1600(2) 0.37607(19) 0.0278(6) Uani 1 1 d . . . C35 C 0.2080(4) 0.1595(2) 0.40549(19) 0.0268(6) Uani 1 1 d . . . H35 H 0.1301 0.1629 0.3648 0.032 Uiso 1 1 calc R . . C36 C 0.1597(3) 0.1540(2) 0.49493(17) 0.0201(5) Uani 1 1 d . . . C37 C 0.5749(3) 0.1315(3) 0.5930(2) 0.0267(6) Uani 1 1 d . . . H37A H 0.6668 0.0947 0.5666 0.040 Uiso 1 1 calc R . . H37B H 0.5340 0.0885 0.6434 0.040 Uiso 1 1 calc R . . H37C H 0.6053 0.2025 0.6104 0.040 Uiso 1 1 calc R . . C38 C 0.4210(5) 0.1665(4) 0.2787(2) 0.0482(9) Uani 1 1 d . . . H38A H 0.5278 0.1945 0.2701 0.072 Uiso 1 1 calc R . . H38B H 0.3484 0.2147 0.2485 0.072 Uiso 1 1 calc R . . H38C H 0.4184 0.0944 0.2562 0.072 Uiso 1 1 calc R . . C39 C -0.0166(3) 0.1524(3) 0.5259(2) 0.0284(6) Uani 1 1 d . . . H39A H -0.0811 0.1553 0.4763 0.043 Uiso 1 1 calc R . . H39B H -0.0416 0.2148 0.5603 0.043 Uiso 1 1 calc R . . H39C H -0.0385 0.0859 0.5606 0.043 Uiso 1 1 calc R . . N1 N 0.2234(3) 0.18885(18) 0.78768(14) 0.0186(4) Uani 1 1 d . . . N2 N 0.2356(2) 0.14773(18) 0.64836(14) 0.0172(4) Uani 1 1 d . . . N3 N 0.1210(3) 0.0256(2) 0.85864(15) 0.0260(5) Uani 1 1 d . . . Cl1 Cl 0.58740(8) 0.37119(7) 0.73087(5) 0.03382(18) Uani 1 1 d . . . Rh1 Rh 0.31885(2) 0.390881(18) 0.683434(14) 0.01927(7) Uani 1 1 d . . . O1 O 0.1553(2) -0.03675(16) 0.65969(12) 0.0245(4) Uani 1 1 d . . . H11 H 0.162(4) 0.3483(13) 0.5483(18) 0.020 Uiso 1 1 d D . . H12 H -0.010(3) 0.3798(19) 0.675(2) 0.020 Uiso 1 1 d D . . H15 H 0.363(4) 0.558(3) 0.7779(13) 0.036 Uiso 1 1 d D . . H16 H 0.4979(5) 0.563(3) 0.640(2) 0.036 Uiso 1 1 d 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 C1 0.0137(11) 0.0229(14) 0.0144(12) -0.0033(10) -0.0045(8) -0.0002(9) C2 0.0221(12) 0.0168(13) 0.0164(13) -0.0023(10) -0.0050(9) -0.0012(9) C3 0.0174(12) 0.0200(14) 0.0172(13) 0.0000(11) -0.0021(9) -0.0025(9) C4 0.0548(19) 0.0196(15) 0.0195(15) 0.0008(12) -0.0033(12) -0.0114(13) C5 0.053(2) 0.034(2) 0.054(2) 0.0017(18) -0.0101(17) -0.0153(16) C6 0.051(2) 0.030(2) 0.053(2) 0.0094(17) -0.0021(16) -0.0062(14) C11 0.0241(13) 0.0156(13) 0.0242(14) -0.0007(11) -0.0108(10) -0.0027(10) C12 0.0249(14) 0.0183(14) 0.0250(15) 0.0064(11) -0.0047(10) -0.0029(10) C13 0.0382(18) 0.041(2) 0.0361(19) -0.0095(16) -0.0072(13) 0.0097(14) C14 0.065(2) 0.0333(19) 0.041(2) -0.0196(16) -0.0173(17) 0.0159(17) C15 0.0506(19) 0.0200(15) 0.0409(19) -0.0096(13) -0.0207(15) -0.0050(13) C16 0.0420(18) 0.0207(16) 0.047(2) 0.0066(14) -0.0190(14) -0.0132(12) C17 0.057(2) 0.0268(17) 0.044(2) 0.0154(15) -0.0217(16) -0.0136(15) C18 0.0411(17) 0.0329(18) 0.0247(16) 0.0082(13) -0.0102(12) -0.0080(13) C21 0.0287(13) 0.0164(13) 0.0138(12) -0.0015(10) -0.0026(9) -0.0071(10) C22 0.0271(14) 0.0210(15) 0.0228(14) -0.0010(11) -0.0047(10) -0.0025(10) C23 0.0364(16) 0.0278(16) 0.0218(15) -0.0014(12) -0.0133(11) -0.0035(12) C24 0.0480(18) 0.0219(15) 0.0172(14) -0.0027(12) -0.0078(11) -0.0047(12) C25 0.0406(17) 0.0217(15) 0.0213(15) -0.0034(12) -0.0002(11) 0.0048(11) C26 0.0297(14) 0.0187(14) 0.0183(13) 0.0019(11) -0.0009(10) -0.0005(10) C27 0.0321(16) 0.0319(18) 0.0356(18) -0.0065(14) -0.0109(12) 0.0068(12) C28 0.074(3) 0.038(2) 0.0313(19) -0.0157(16) -0.0177(16) -0.0020(17) C29 0.0316(16) 0.044(2) 0.0267(17) -0.0015(15) -0.0014(11) 0.0062(13) C31 0.0215(12) 0.0155(13) 0.0143(12) -0.0014(10) 0.0028(9) -0.0044(9) C32 0.0274(14) 0.0122(13) 0.0223(15) -0.0002(11) 0.0014(10) -0.0047(9) C33 0.0300(15) 0.0216(15) 0.0244(15) -0.0038(12) 0.0113(11) -0.0079(11) C34 0.0464(17) 0.0199(14) 0.0169(14) -0.0018(11) 0.0027(11) -0.0088(12) C35 0.0396(16) 0.0219(15) 0.0198(14) -0.0028(11) -0.0073(11) -0.0035(11) C36 0.0256(13) 0.0147(13) 0.0206(13) -0.0028(10) -0.0051(10) -0.0018(10) C37 0.0199(13) 0.0302(16) 0.0302(16) -0.0030(13) -0.0005(10) -0.0009(10) C38 0.074(3) 0.050(2) 0.0206(18) -0.0047(16) 0.0069(15) -0.0157(18) C39 0.0236(14) 0.0332(17) 0.0297(16) -0.0081(13) -0.0071(11) -0.0014(11) N1 0.0249(11) 0.0173(11) 0.0139(11) 0.0001(9) -0.0030(8) -0.0022(8) N2 0.0182(10) 0.0174(11) 0.0161(11) -0.0008(9) -0.0005(7) -0.0038(8) N3 0.0390(14) 0.0229(13) 0.0166(12) 0.0004(10) -0.0033(9) -0.0071(10) Cl1 0.0265(4) 0.0353(4) 0.0415(4) -0.0026(3) -0.0144(3) -0.0068(3) Rh1 0.02200(11) 0.01726(11) 0.01934(11) -0.00085(7) -0.00617(8) -0.00501(8) O1 0.0351(11) 0.0198(10) 0.0190(10) -0.0045(8) 0.0011(7) -0.0079(8) _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 C1 N1 1.371(3) . ? C1 N2 1.417(3) . ? C1 Rh1 1.998(3) . ? C2 N3 1.268(4) . ? C2 N1 1.431(3) . ? C2 C3 1.524(4) . ? C3 O1 1.228(3) . ? C3 N2 1.404(3) . ? C4 N3 1.486(4) . ? C4 C5 1.535(5) . ? C4 C6 1.544(5) . ? C4 H4 0.9800 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C11 C12 1.415(4) . ? C11 C18 1.523(4) . ? C11 Rh1 2.135(3) . ? C11 H11 0.9700(3) . ? C12 C13 1.546(4) . ? C12 Rh1 2.186(3) . ? C12 H12 0.9700(4) . ? C13 C14 1.544(5) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.537(5) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.380(5) . ? C15 Rh1 2.259(3) . ? C15 H15 0.9700(3) . ? C16 C17 1.529(5) . ? C16 Rh1 2.300(3) . ? C16 H16 0.9700(6) . ? C17 C18 1.547(5) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C21 C22 1.416(4) . ? C21 C26 1.421(4) . ? C21 N1 1.465(3) . ? C22 C23 1.404(4) . ? C22 C27 1.535(4) . ? C23 C24 1.417(4) . ? C23 H23 0.9300 . ? C24 C25 1.405(4) . ? C24 C28 1.530(4) . ? C25 C26 1.401(4) . ? C25 H25 0.9300 . ? C26 C29 1.521(4) . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C31 C32 1.414(4) . ? C31 C36 1.414(4) . ? C31 N2 1.462(3) . ? C32 C33 1.410(4) . ? C32 C37 1.517(4) . ? C33 C34 1.402(4) . ? C33 H33 0.9300 . ? C34 C35 1.405(4) . ? C34 C38 1.528(4) . ? C35 C36 1.407(4) . ? C35 H35 0.9300 . ? C36 C39 1.519(4) . ? C37 H37A 0.9600 . ? C37 H37B 0.9600 . ? C37 H37C 0.9600 . ? C38 H38A 0.9600 . ? C38 H38B 0.9600 . ? C38 H38C 0.9600 . ? C39 H39A 0.9600 . ? C39 H39B 0.9600 . ? C39 H39C 0.9600 . ? Cl1 Rh1 2.4071(15) . ? 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 N1 C1 N2 105.5(2) . . ? N1 C1 Rh1 121.80(18) . . ? N2 C1 Rh1 132.28(18) . . ? N3 C2 N1 122.2(2) . . ? N3 C2 C3 133.9(3) . . ? N1 C2 C3 104.0(2) . . ? O1 C3 N2 126.2(2) . . ? O1 C3 C2 129.3(2) . . ? N2 C3 C2 104.4(2) . . ? N3 C4 C5 107.3(3) . . ? N3 C4 C6 107.3(3) . . ? C5 C4 C6 111.1(3) . . ? N3 C4 H4 110.4 . . ? C5 C4 H4 110.4 . . ? C6 C4 H4 110.4 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C12 C11 C18 126.4(3) . . ? C12 C11 Rh1 72.84(15) . . ? C18 C11 Rh1 110.47(18) . . ? C12 C11 H11 118.2(18) . . ? C18 C11 H11 111.3(18) . . ? Rh1 C11 H11 108.1(18) . . ? C11 C12 C13 124.4(3) . . ? C11 C12 Rh1 68.95(14) . . ? C13 C12 Rh1 114.03(19) . . ? C11 C12 H12 121.6(19) . . ? C13 C12 H12 106.3(19) . . ? Rh1 C12 H12 117.0(18) . . ? C12 C13 C14 112.6(3) . . ? C12 C13 H13A 109.1 . . ? C14 C13 H13A 109.1 . . ? C12 C13 H13B 109.1 . . ? C14 C13 H13B 109.1 . . ? H13A C13 H13B 107.8 . . ? C15 C14 C13 113.6(3) . . ? C15 C14 H14A 108.8 . . ? C13 C14 H14A 108.8 . . ? C15 C14 H14B 108.8 . . ? C13 C14 H14B 108.8 . . ? H14A C14 H14B 107.7 . . ? C16 C15 C14 125.8(3) . . ? C16 C15 Rh1 74.02(19) . . ? C14 C15 Rh1 108.0(2) . . ? C16 C15 H15 123(2) . . ? C14 C15 H15 111(2) . . ? Rh1 C15 H15 99(2) . . ? C15 C16 C17 125.5(3) . . ? C15 C16 Rh1 70.77(18) . . ? C17 C16 Rh1 110.5(2) . . ? C15 C16 H16 116(2) . . ? C17 C16 H16 117(2) . . ? Rh1 C16 H16 99(2) . . ? C16 C17 C18 112.1(3) . . ? C16 C17 H17A 109.2 . . ? C18 C17 H17A 109.2 . . ? C16 C17 H17B 109.2 . . ? C18 C17 H17B 109.2 . . ? H17A C17 H17B 107.9 . . ? C11 C18 C17 114.1(3) . . ? C11 C18 H18A 108.7 . . ? C17 C18 H18A 108.7 . . ? C11 C18 H18B 108.7 . . ? C17 C18 H18B 108.7 . . ? H18A C18 H18B 107.6 . . ? C22 C21 C26 122.2(2) . . ? C22 C21 N1 117.4(2) . . ? C26 C21 N1 120.4(2) . . ? C23 C22 C21 117.1(3) . . ? C23 C22 C27 120.9(3) . . ? C21 C22 C27 122.0(3) . . ? C22 C23 C24 122.5(3) . . ? C22 C23 H23 118.7 . . ? C24 C23 H23 118.7 . . ? C25 C24 C23 117.9(3) . . ? C25 C24 C28 121.5(3) . . ? C23 C24 C28 120.6(3) . . ? C26 C25 C24 122.2(3) . . ? C26 C25 H25 118.9 . . ? C24 C25 H25 118.9 . . ? C25 C26 C21 117.7(3) . . ? C25 C26 C29 120.7(3) . . ? C21 C26 C29 121.5(3) . . ? C22 C27 H27A 109.5 . . ? C22 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C22 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C24 C28 H28A 109.5 . . ? C24 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C24 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C26 C29 H29A 109.5 . . ? C26 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C26 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C32 C31 C36 122.3(2) . . ? C32 C31 N2 118.7(2) . . ? C36 C31 N2 119.0(2) . . ? C33 C32 C31 117.7(3) . . ? C33 C32 C37 120.5(2) . . ? C31 C32 C37 121.7(3) . . ? C34 C33 C32 121.5(3) . . ? C34 C33 H33 119.3 . . ? C32 C33 H33 119.3 . . ? C33 C34 C35 119.1(3) . . ? C33 C34 C38 119.8(3) . . ? C35 C34 C38 121.1(3) . . ? C34 C35 C36 121.7(3) . . ? C34 C35 H35 119.1 . . ? C36 C35 H35 119.1 . . ? C35 C36 C31 117.5(2) . . ? C35 C36 C39 121.2(2) . . ? C31 C36 C39 121.3(2) . . ? C32 C37 H37A 109.5 . . ? C32 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C32 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C34 C38 H38A 109.5 . . ? C34 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C34 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C36 C39 H39A 109.5 . . ? C36 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C36 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C1 N1 C2 113.2(2) . . ? C1 N1 C21 123.8(2) . . ? C2 N1 C21 122.7(2) . . ? C3 N2 C1 112.8(2) . . ? C3 N2 C31 120.9(2) . . ? C1 N2 C31 125.6(2) . . ? C2 N3 C4 120.8(2) . . ? C1 Rh1 C11 94.80(10) . . ? C1 Rh1 C12 90.86(10) . . ? C11 Rh1 C12 38.20(11) . . ? C1 Rh1 C15 149.94(12) . . ? C11 Rh1 C15 95.66(11) . . ? C12 Rh1 C15 80.34(11) . . ? C1 Rh1 C16 173.99(11) . . ? C11 Rh1 C16 80.37(10) . . ? C12 Rh1 C16 87.53(10) . . ? C15 Rh1 C16 35.21(13) . . ? C1 Rh1 Cl1 95.60(7) . . ? C11 Rh1 Cl1 147.31(8) . . ? C12 Rh1 Cl1 170.47(8) . . ? C15 Rh1 Cl1 90.61(8) . . ? C16 Rh1 Cl1 86.74(7) . . ? _vrf_PLAT021_complex_8 ; PROBLEM: Ratio Unique / Expected Reflections too High RESPONSE: The crystal used for data collection was found to display non-merohedral twinning. Both components of the twin were indexed with the program CELL_NOW (Bruker AXS Inc., Madison, WI, 2004). The second twin component can be related to the first component by 180 deg rotation around the a axis. Integrated intensities for the reflections from the two components were written into a SHELXL-93 HKLF 5 reflection file with the data integration program TWINABS (V1.05; Bruker AXS Inc., Madison, WI) , using all reflection data (exactly overlapped, partially overlapped and non-overlapped). ; # 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