# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name 'Athanasia Dervisi' 'Dirk J Beetstra' 'Abeer Binobaid' 'Kingsley Cavell' 'A Fallis' 'Manuel Iglesias' 'Benson M Kariuki' _publ_contact_author_name 'Athanasia Dervisi' _publ_contact_author_email DERVISIA@CARDIFF.AC.UK _publ_section_title ; Expanded Ring and Functionalised Expanded Ring N-Heterocyclic Carbenes as Ligands in Catalysis ; # Attachment 'askjc40.CIF' data_asKJC40 _database_code_depnum_ccdc_archive 'CCDC 733086' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H24 N3, I' _chemical_formula_sum 'C19 H24 I N3' _chemical_formula_weight 421.31 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 0.0000 0.0000 '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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.432(3) _cell_length_b 17.575(4) _cell_length_c 7.9907(16) _cell_angle_alpha 90.00 _cell_angle_beta 104.21(3) _cell_angle_gamma 90.00 _cell_volume 1828.6(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3436 _cell_measurement_theta_min 2.95 _cell_measurement_theta_max 27.00 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.530 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 848 _exptl_absorpt_coefficient_mu 1.755 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.404 _exptl_absorpt_correction_T_max 0.753 _exptl_absorpt_process_details Denzo/scalepack _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method 'CCD scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6579 _diffrn_reflns_av_R_equivalents 0.0278 _diffrn_reflns_av_sigmaI/netI 0.0437 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 27.00 _reflns_number_total 3964 _reflns_number_gt 3436 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'cOLLECT,Nonius BV, 1997-2001' _computing_cell_refinement DENZO/SCALEPACK _computing_data_reduction DENZO/SCALEPACK _computing_structure_solution SHELXs-97 _computing_structure_refinement SHELXL-97 _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^)+(0.0065P)^2^+1.6367P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3964 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0341 _refine_ls_R_factor_gt 0.0269 _refine_ls_wR_factor_ref 0.0591 _refine_ls_wR_factor_gt 0.0566 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.311617(12) 0.075408(8) 0.78471(2) 0.02311(6) Uani 1 1 d . . . N1 N 0.84815(15) 0.39292(10) 0.4537(2) 0.0172(4) Uani 1 1 d . . . C1 C 0.78130(18) 0.33710(13) 0.4272(3) 0.0178(5) Uani 1 1 d . . . H1 H 0.8071 0.2878 0.4621 0.021 Uiso 1 1 calc R . . N2 N 0.68140(15) 0.34249(10) 0.3567(2) 0.0176(4) Uani 1 1 d . . . C2 C 0.83036(19) 0.46995(13) 0.3707(3) 0.0210(5) Uani 1 1 d . . . H2A H 0.8969 0.4913 0.3610 0.025 Uiso 1 1 calc R . . H2B H 0.8017 0.5043 0.4452 0.025 Uiso 1 1 calc R . . N3 N 0.67772(16) 0.20959(11) 0.3419(3) 0.0224(5) Uani 1 1 d . . . C3 C 0.7571(2) 0.46675(14) 0.1923(3) 0.0232(5) Uani 1 1 d . . . H3A H 0.7727 0.4208 0.1316 0.028 Uiso 1 1 calc R . . H3B H 0.7692 0.5117 0.1253 0.028 Uiso 1 1 calc R . . C4 C 0.6440(2) 0.46489(14) 0.1963(3) 0.0236(5) Uani 1 1 d . . . H4A H 0.6198 0.5174 0.2077 0.028 Uiso 1 1 calc R . . H4B H 0.6028 0.4435 0.0864 0.028 Uiso 1 1 calc R . . C5 C 0.62847(19) 0.41701(12) 0.3458(3) 0.0207(5) Uani 1 1 d . . . H5A H 0.6548 0.4452 0.4550 0.025 Uiso 1 1 calc R . . H5B H 0.5541 0.4084 0.3320 0.025 Uiso 1 1 calc R . . C6 C 0.95289(18) 0.37411(12) 0.5471(3) 0.0170(5) Uani 1 1 d . . . C7 C 0.98115(18) 0.38540(12) 0.7262(3) 0.0182(5) Uani 1 1 d . . . C8 C 1.08193(19) 0.36588(13) 0.8116(3) 0.0193(5) Uani 1 1 d . . . H8 H 1.1036 0.3728 0.9330 0.023 Uiso 1 1 calc R . . C9 C 1.15115(19) 0.33680(13) 0.7250(3) 0.0201(5) Uani 1 1 d . . . C10 C 1.1194(2) 0.32734(13) 0.5471(3) 0.0229(5) Uani 1 1 d . . . H10 H 1.1666 0.3078 0.4867 0.027 Uiso 1 1 calc R . . C11 C 1.0201(2) 0.34575(13) 0.4549(3) 0.0216(5) Uani 1 1 d . . . C12 C 0.9070(2) 0.41572(16) 0.8233(3) 0.0292(6) Uani 1 1 d . . . H12A H 0.8670 0.4573 0.7575 0.044 Uiso 1 1 calc R . . H12B H 0.9452 0.4347 0.9361 0.044 Uiso 1 1 calc R . . H12C H 0.8606 0.3749 0.8395 0.044 Uiso 1 1 calc R . . C13 C 1.2599(2) 0.31650(14) 0.8184(4) 0.0272(6) Uani 1 1 d . . . H13A H 1.2684 0.3227 0.9430 0.041 Uiso 1 1 calc R . . H13B H 1.3079 0.3501 0.7796 0.041 Uiso 1 1 calc R . . H13C H 1.2738 0.2635 0.7932 0.041 Uiso 1 1 calc R . . C14 C 0.9893(2) 0.33467(17) 0.2617(3) 0.0363(7) Uani 1 1 d . . . H14A H 0.9392 0.2932 0.2333 0.054 Uiso 1 1 calc R . . H14B H 1.0501 0.3219 0.2203 0.054 Uiso 1 1 calc R . . H14C H 0.9586 0.3817 0.2062 0.054 Uiso 1 1 calc R . . C15 C 0.62532(18) 0.27351(13) 0.2961(3) 0.0176(5) Uani 1 1 d . . . C16 C 0.52661(19) 0.27748(14) 0.1924(3) 0.0226(5) Uani 1 1 d . . . H16 H 0.4926 0.3248 0.1631 0.027 Uiso 1 1 calc R . . C17 C 0.4794(2) 0.20877(14) 0.1331(3) 0.0250(6) Uani 1 1 d . . . H17 H 0.4119 0.2084 0.0603 0.030 Uiso 1 1 calc R . . C18 C 0.53091(19) 0.14120(14) 0.1802(3) 0.0234(5) Uani 1 1 d . . . H18 H 0.4993 0.0938 0.1421 0.028 Uiso 1 1 calc R . . C19 C 0.6294(2) 0.14411(14) 0.2840(3) 0.0237(5) Uani 1 1 d . . . H19 H 0.6650 0.0976 0.3163 0.028 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 I1 0.02447(10) 0.01947(9) 0.02331(10) 0.00098(6) 0.00189(7) -0.00444(6) N1 0.0163(10) 0.0155(9) 0.0178(10) 0.0007(8) 0.0004(8) 0.0007(8) C1 0.0186(12) 0.0187(11) 0.0154(12) 0.0002(9) 0.0025(9) -0.0006(9) N2 0.0147(10) 0.0159(9) 0.0210(11) -0.0005(8) 0.0023(8) 0.0000(8) C2 0.0228(13) 0.0174(11) 0.0210(13) 0.0039(9) 0.0018(10) -0.0028(9) N3 0.0203(11) 0.0190(10) 0.0251(12) -0.0010(8) 0.0001(9) -0.0020(8) C3 0.0261(14) 0.0220(12) 0.0195(13) 0.0056(10) 0.0018(11) 0.0021(10) C4 0.0223(14) 0.0222(12) 0.0231(13) 0.0017(10) -0.0007(11) 0.0048(10) C5 0.0197(13) 0.0171(11) 0.0238(13) -0.0045(9) 0.0024(10) 0.0035(9) C6 0.0125(11) 0.0157(11) 0.0204(12) 0.0014(9) -0.0006(9) -0.0016(8) C7 0.0180(12) 0.0182(11) 0.0191(12) 0.0014(9) 0.0059(10) -0.0011(9) C8 0.0179(13) 0.0218(12) 0.0172(12) 0.0003(9) 0.0025(10) -0.0013(9) C9 0.0156(12) 0.0171(11) 0.0269(13) 0.0010(10) 0.0038(10) -0.0013(9) C10 0.0240(14) 0.0211(12) 0.0252(13) -0.0016(10) 0.0092(11) 0.0032(10) C11 0.0268(14) 0.0181(11) 0.0204(13) 0.0003(9) 0.0066(11) 0.0014(10) C12 0.0231(14) 0.0436(16) 0.0216(14) 0.0012(11) 0.0066(11) 0.0091(12) C13 0.0196(14) 0.0265(13) 0.0342(15) -0.0017(11) 0.0040(11) 0.0037(10) C14 0.0424(19) 0.0460(17) 0.0191(14) -0.0042(12) 0.0048(13) 0.0139(14) C15 0.0173(12) 0.0176(11) 0.0180(12) -0.0029(9) 0.0046(9) -0.0036(9) C16 0.0184(13) 0.0223(12) 0.0244(13) -0.0022(10) 0.0003(10) 0.0009(10) C17 0.0164(13) 0.0316(14) 0.0253(14) -0.0031(10) 0.0017(11) -0.0031(10) C18 0.0198(13) 0.0238(12) 0.0271(14) -0.0048(10) 0.0068(11) -0.0073(10) C19 0.0247(14) 0.0188(12) 0.0277(14) -0.0001(10) 0.0064(11) -0.0015(10) _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 N1 C1 1.312(3) . ? N1 C6 1.459(3) . ? N1 C2 1.501(3) . ? C1 N2 1.325(3) . ? N2 C15 1.447(3) . ? N2 C5 1.483(3) . ? C2 C3 1.521(3) . ? N3 C15 1.329(3) . ? N3 C19 1.346(3) . ? C3 C4 1.528(4) . ? C4 C5 1.517(3) . ? C6 C11 1.390(3) . ? C6 C7 1.402(3) . ? C7 C8 1.401(3) . ? C7 C12 1.502(3) . ? C8 C9 1.386(3) . ? C9 C10 1.390(3) . ? C9 C13 1.511(3) . ? C10 C11 1.394(3) . ? C11 C14 1.509(3) . ? C15 C16 1.382(3) . ? C16 C17 1.392(3) . ? C17 C18 1.379(3) . ? C18 C19 1.379(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C6 116.68(18) . . ? C1 N1 C2 125.11(19) . . ? C6 N1 C2 117.34(18) . . ? N1 C1 N2 126.6(2) . . ? C1 N2 C15 118.17(19) . . ? C1 N2 C5 120.61(19) . . ? C15 N2 C5 121.19(19) . . ? N1 C2 C3 112.14(18) . . ? C15 N3 C19 116.8(2) . . ? C2 C3 C4 113.5(2) . . ? C5 C4 C3 111.0(2) . . ? N2 C5 C4 112.3(2) . . ? C11 C6 C7 122.9(2) . . ? C11 C6 N1 118.7(2) . . ? C7 C6 N1 118.4(2) . . ? C8 C7 C6 116.7(2) . . ? C8 C7 C12 121.3(2) . . ? C6 C7 C12 122.0(2) . . ? C9 C8 C7 122.3(2) . . ? C8 C9 C10 118.7(2) . . ? C8 C9 C13 121.7(2) . . ? C10 C9 C13 119.6(2) . . ? C9 C10 C11 121.7(2) . . ? C6 C11 C10 117.7(2) . . ? C6 C11 C14 122.5(2) . . ? C10 C11 C14 119.8(2) . . ? N3 C15 C16 125.0(2) . . ? N3 C15 N2 114.80(19) . . ? C16 C15 N2 120.2(2) . . ? C15 C16 C17 116.8(2) . . ? C18 C17 C16 119.9(2) . . ? C19 C18 C17 118.4(2) . . ? N3 C19 C18 123.3(2) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.341 _refine_diff_density_min -0.564 _refine_diff_density_rms 0.082 # Attachment 'kjc0707.cif' data_kjc0707 _database_code_depnum_ccdc_archive 'CCDC 733087' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H30 N3, I' _chemical_formula_sum 'C22 H30 I N3' _chemical_formula_weight 463.39 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 0.0000 0.0000 '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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.47200(10) _cell_length_b 33.8750(6) _cell_length_c 8.3760(2) _cell_angle_alpha 90.00 _cell_angle_beta 116.8380(10) _cell_angle_gamma 90.00 _cell_volume 2144.90(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3366 _cell_measurement_theta_min 2.95 _cell_measurement_theta_max 27.49 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.435 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 1.503 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7531 _exptl_absorpt_correction_T_max 0.8642 _exptl_absorpt_process_details Denzo/Scalepack _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'CCD scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11030 _diffrn_reflns_av_R_equivalents 0.1177 _diffrn_reflns_av_sigmaI/netI 0.0915 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 43 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.95 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4407 _reflns_number_gt 3366 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'cOLLECT,Nonius BV, 1997-2001' _computing_cell_refinement DENZO/SCALEPACK _computing_data_reduction DENZO/SCALEPACK _computing_structure_solution SHELXs-97 _computing_structure_refinement SHELXL-97 _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^)+(0.1388P)^2^+10.1668P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4407 _refine_ls_number_parameters 239 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1021 _refine_ls_R_factor_gt 0.0811 _refine_ls_wR_factor_ref 0.2361 _refine_ls_wR_factor_gt 0.2183 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C5 C 0.7639(9) -0.0014(2) 0.5028(10) 0.0232(15) Uani 1 1 d . . . H5 H 0.8187 -0.0253 0.4954 0.028 Uiso 1 1 calc R . . C8 C 0.2222(8) 0.17725(19) 0.2985(8) 0.0155(13) Uani 1 1 d . . . C9 C 0.6236(7) 0.07038(19) 0.5368(8) 0.0121(12) Uani 1 1 d . . . C11 C 0.6439(9) 0.1296(2) 0.7307(8) 0.0205(14) Uani 1 1 d . . . H11A H 0.5573 0.1336 0.7783 0.025 Uiso 1 1 calc R . . H11B H 0.6756 0.1559 0.7023 0.025 Uiso 1 1 calc R . . C12 C 0.8083(8) 0.1104(2) 0.8738(9) 0.0205(14) Uani 1 1 d . . . H12A H 0.8742 0.1302 0.9671 0.025 Uiso 1 1 calc R . . H12B H 0.8854 0.1019 0.8198 0.025 Uiso 1 1 calc R . . C14 C -0.0779(9) 0.2152(2) 0.0556(9) 0.0261(16) Uani 1 1 d . . . H14 H -0.1824 0.2276 -0.0305 0.031 Uiso 1 1 calc R . . C15 C 0.0673(8) 0.1759(2) 0.3230(9) 0.0182(13) Uani 1 1 d . . . C16 C 0.6312(9) 0.0480(2) 0.8199(9) 0.0184(13) Uani 1 1 d . . . H16A H 0.6313 0.0221 0.8745 0.022 Uiso 1 1 calc R . . H16B H 0.5122 0.0598 0.7785 0.022 Uiso 1 1 calc R . . C17 C 0.4030(9) 0.2013(2) 0.1436(9) 0.0230(15) Uani 1 1 d . . . H17 H 0.5006 0.1906 0.2562 0.028 Uiso 1 1 calc R . . C18 C -0.0801(9) 0.1962(2) 0.1968(9) 0.0214(14) Uani 1 1 d . . . H18 H -0.1854 0.1966 0.2106 0.026 Uiso 1 1 calc R . . C19 C 0.7039(9) 0.0259(2) 0.3622(9) 0.0209(14) Uani 1 1 d . . . H19 H 0.7092 0.0197 0.2541 0.025 Uiso 1 1 calc R . . C20 C 0.4194(8) 0.1250(2) 0.4189(8) 0.0164(13) Uani 1 1 d . . . H20 H 0.3577 0.1116 0.3081 0.020 Uiso 1 1 calc R . . C21 C 0.6364(8) 0.0620(2) 0.3807(9) 0.0178(13) Uani 1 1 d . . . H21 H 0.5992 0.0809 0.2870 0.021 Uiso 1 1 calc R . . C22 C 0.7415(8) 0.0073(2) 0.6540(9) 0.0201(14) Uani 1 1 d . . . H22 H 0.7777 -0.0112 0.7492 0.024 Uiso 1 1 calc R . . C23 C 0.7693(9) 0.0750(2) 0.9612(9) 0.0242(16) Uani 1 1 d . . . H23A H 0.7247 0.0841 1.0456 0.029 Uiso 1 1 calc R . . H23B H 0.8797 0.0599 1.0300 0.029 Uiso 1 1 calc R . . C24 C 0.4478(10) 0.2440(2) 0.1230(12) 0.0327(18) Uani 1 1 d . . . H24A H 0.3606 0.2542 0.0073 0.049 Uiso 1 1 calc R . . H24B H 0.5660 0.2451 0.1291 0.049 Uiso 1 1 calc R . . H24C H 0.4458 0.2600 0.2195 0.049 Uiso 1 1 calc R . . C25 C 0.2325(9) 0.1984(2) 0.1601(8) 0.0185(13) Uani 1 1 d . . . C26 C 0.0764(9) 0.2169(2) 0.0359(9) 0.0238(15) Uani 1 1 d . . . H26 H 0.0764 0.2306 -0.0628 0.029 Uiso 1 1 calc R . . C28 C -0.0581(11) 0.1701(3) 0.5469(11) 0.0358(19) Uani 1 1 d . . . H28A H -0.0374 0.1985 0.5672 0.054 Uiso 1 1 calc R . . H28B H -0.0357 0.1571 0.6597 0.054 Uiso 1 1 calc R . . H28C H -0.1811 0.1655 0.4586 0.054 Uiso 1 1 calc R . . C29 C 0.0653(9) 0.1534(2) 0.4776(9) 0.0222(14) Uani 1 1 d . . . H29 H 0.1878 0.1548 0.5783 0.027 Uiso 1 1 calc R . . C30 C 0.0262(12) 0.1097(3) 0.4285(11) 0.037(2) Uani 1 1 d . . . H30A H -0.0953 0.1068 0.3339 0.056 Uiso 1 1 calc R . . H30B H 0.0399 0.0948 0.5342 0.056 Uiso 1 1 calc R . . H30C H 0.1088 0.0995 0.3860 0.056 Uiso 1 1 calc R . . C31 C 0.3961(14) 0.1771(3) -0.0107(15) 0.054(3) Uani 1 1 d . . . H31A H 0.3892 0.1490 0.0134 0.081 Uiso 1 1 calc R . . H31B H 0.5031 0.1820 -0.0250 0.081 Uiso 1 1 calc R . . H31C H 0.2917 0.1847 -0.1206 0.081 Uiso 1 1 calc R . . N3 N 0.6680(7) 0.04226(17) 0.6657(7) 0.0141(11) Uani 1 1 d . . . N6 N 0.3761(7) 0.15941(16) 0.4360(7) 0.0151(11) Uani 1 1 d . . . N7 N 0.5589(6) 0.10600(16) 0.5627(7) 0.0133(11) Uani 1 1 d . . . I1 I 0.23163(6) 0.055182(15) 0.93476(6) 0.0291(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C5 0.025(3) 0.017(4) 0.028(3) 0.000(3) 0.012(3) 0.005(3) C8 0.021(3) 0.005(3) 0.017(3) 0.003(2) 0.005(2) 0.003(2) C9 0.014(3) 0.002(3) 0.017(3) -0.001(2) 0.005(2) 0.003(2) C11 0.033(3) 0.007(3) 0.018(3) 0.001(3) 0.008(3) 0.007(3) C12 0.021(3) 0.016(4) 0.017(3) 0.002(3) 0.001(2) 0.007(3) C14 0.030(4) 0.009(4) 0.025(3) 0.004(3) 0.000(3) 0.012(3) C15 0.021(3) 0.007(3) 0.023(3) -0.001(3) 0.007(2) 0.001(2) C16 0.030(3) 0.008(3) 0.018(3) 0.004(3) 0.012(3) 0.006(3) C17 0.029(3) 0.018(4) 0.020(3) 0.007(3) 0.009(3) 0.003(3) C18 0.019(3) 0.012(4) 0.029(3) -0.002(3) 0.008(3) 0.000(2) C19 0.029(3) 0.014(4) 0.023(3) 0.001(3) 0.016(3) 0.003(3) C20 0.022(3) 0.011(3) 0.015(3) 0.004(3) 0.008(2) 0.001(2) C21 0.023(3) 0.007(3) 0.021(3) 0.001(3) 0.007(3) 0.003(2) C22 0.025(3) 0.006(3) 0.023(3) 0.005(3) 0.006(3) 0.004(2) C23 0.031(4) 0.021(4) 0.015(3) 0.004(3) 0.005(3) 0.002(3) C24 0.036(4) 0.016(4) 0.049(5) -0.005(4) 0.023(4) -0.003(3) C25 0.028(3) 0.008(3) 0.018(3) 0.001(2) 0.008(3) 0.002(3) C26 0.031(4) 0.015(4) 0.022(3) 0.010(3) 0.009(3) 0.009(3) C28 0.040(4) 0.034(5) 0.040(4) 0.007(4) 0.024(4) 0.008(4) C29 0.021(3) 0.018(4) 0.024(3) 0.003(3) 0.007(3) -0.001(3) C30 0.047(5) 0.026(5) 0.037(4) 0.002(4) 0.018(4) -0.013(4) C31 0.063(6) 0.045(7) 0.074(7) -0.041(6) 0.049(6) -0.019(5) N3 0.024(3) 0.003(3) 0.016(2) 0.004(2) 0.009(2) 0.005(2) N6 0.021(2) 0.008(3) 0.013(2) 0.002(2) 0.0056(19) 0.003(2) N7 0.018(2) 0.004(3) 0.014(2) 0.002(2) 0.0042(19) 0.0033(19) I1 0.0360(3) 0.0220(3) 0.0299(3) 0.0033(2) 0.0153(2) 0.00694(19) _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 C5 C22 1.394(10) . ? C5 C19 1.399(11) . ? C8 C25 1.399(9) . ? C8 C15 1.417(9) . ? C8 N6 1.427(8) . ? C9 N3 1.359(8) . ? C9 N7 1.382(8) . ? C9 C21 1.389(9) . ? C11 N7 1.490(8) . ? C11 C12 1.514(8) . ? C12 C23 1.518(10) . ? C14 C18 1.355(11) . ? C14 C26 1.390(10) . ? C15 C18 1.399(9) . ? C15 C29 1.510(10) . ? C16 N3 1.472(8) . ? C16 C23 1.534(10) . ? C17 C31 1.508(11) . ? C17 C25 1.515(9) . ? C17 C24 1.525(11) . ? C19 C21 1.390(10) . ? C20 N6 1.250(9) . ? C20 N7 1.405(8) . ? C22 N3 1.361(9) . ? C25 C26 1.407(9) . ? C28 C29 1.517(10) . ? C29 C30 1.531(11) . ? 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 C22 C5 C19 118.5(7) . . ? C25 C8 C15 123.0(6) . . ? C25 C8 N6 120.6(6) . . ? C15 C8 N6 116.0(6) . . ? N3 C9 N7 118.3(6) . . ? N3 C9 C21 119.6(6) . . ? N7 C9 C21 122.1(6) . . ? N7 C11 C12 113.4(5) . . ? C11 C12 C23 113.5(6) . . ? C18 C14 C26 120.5(6) . . ? C18 C15 C8 116.4(6) . . ? C18 C15 C29 123.0(6) . . ? C8 C15 C29 120.7(6) . . ? N3 C16 C23 111.4(6) . . ? C31 C17 C25 111.9(6) . . ? C31 C17 C24 109.4(7) . . ? C25 C17 C24 111.6(6) . . ? C14 C18 C15 122.2(6) . . ? C21 C19 C5 120.0(7) . . ? N6 C20 N7 120.3(6) . . ? C9 C21 C19 119.7(6) . . ? N3 C22 C5 120.3(6) . . ? C12 C23 C16 110.8(5) . . ? C8 C25 C26 116.8(6) . . ? C8 C25 C17 121.9(6) . . ? C26 C25 C17 121.4(6) . . ? C14 C26 C25 121.0(6) . . ? C15 C29 C28 114.6(6) . . ? C15 C29 C30 110.1(6) . . ? C28 C29 C30 111.1(7) . . ? C9 N3 C22 121.6(6) . . ? C9 N3 C16 120.8(5) . . ? C22 N3 C16 117.6(5) . . ? C20 N6 C8 120.8(6) . . ? C9 N7 C20 120.3(5) . . ? C9 N7 C11 124.0(5) . . ? C20 N7 C11 115.1(5) . . ? _diffrn_measured_fraction_theta_max 0.897 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.897 _refine_diff_density_max 1.861 _refine_diff_density_min -2.577 _refine_diff_density_rms 0.224 # Attachment 'kjc0715.cif' data_kjc0715 _database_code_depnum_ccdc_archive 'CCDC 733088' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H22 N3, B F4' _chemical_formula_sum 'C18 H22 B F4 N3' _chemical_formula_weight 367.20 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.1180(2) _cell_length_b 17.8690(6) _cell_length_c 8.0030(4) _cell_angle_alpha 90.00 _cell_angle_beta 104.657(2) _cell_angle_gamma 90.00 _cell_volume 1814.90(11) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2577 _cell_measurement_theta_min 2.94 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.344 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9682 _exptl_absorpt_correction_T_max 0.9786 _exptl_absorpt_process_details Denzo/Scalepack _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'CCD scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14070 _diffrn_reflns_av_R_equivalents 0.1454 _diffrn_reflns_av_sigmaI/netI 0.1022 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4124 _reflns_number_gt 2577 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'cOLLECT,Nonius BV, 1997-2001' _computing_cell_refinement DENZO/SCALEPACK _computing_data_reduction DENZO/SCALEPACK _computing_structure_solution SHELXs-97 _computing_structure_refinement SHELXL-97 _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^)+(0.0853P)^2^+0.9222P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.018(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4124 _refine_ls_number_parameters 239 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1176 _refine_ls_R_factor_gt 0.0732 _refine_ls_wR_factor_ref 0.2152 _refine_ls_wR_factor_gt 0.1866 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.27774(18) 0.17086(14) 0.3260(3) 0.0323(6) Uani 1 1 d . . . H1 H 0.3041 0.2191 0.3637 0.039 Uiso 1 1 calc R . . C2 C 0.1336(2) 0.09322(15) 0.1664(4) 0.0405(7) Uani 1 1 d . . . H2A H 0.1414 0.0834 0.0485 0.049 Uiso 1 1 calc R . . H2B H 0.0574 0.0936 0.1617 0.049 Uiso 1 1 calc R . . C3 C 0.1879(2) 0.03219(15) 0.2873(4) 0.0453(7) Uani 1 1 d . . . H3A H 0.1637 -0.0172 0.2366 0.054 Uiso 1 1 calc R . . H3B H 0.1681 0.0365 0.3984 0.054 Uiso 1 1 calc R . . C4 C 0.3067(2) 0.03694(14) 0.3203(4) 0.0411(7) Uani 1 1 d . . . H4A H 0.3405 0.0008 0.4114 0.049 Uiso 1 1 calc R . . H4B H 0.3281 0.0244 0.2137 0.049 Uiso 1 1 calc R . . C5 C 0.12454(18) 0.23497(14) 0.1683(3) 0.0316(6) Uani 1 1 d . . . C6 C 0.02770(19) 0.23393(17) 0.0491(3) 0.0405(7) Uani 1 1 d . . . H6 H -0.0052 0.1882 0.0050 0.049 Uiso 1 1 calc R . . C7 C -0.01951(19) 0.30225(17) -0.0033(4) 0.0435(7) Uani 1 1 d . . . H7 H -0.0856 0.3040 -0.0864 0.052 Uiso 1 1 calc R . . C8 C 0.0292(2) 0.36739(17) 0.0649(4) 0.0430(7) Uani 1 1 d . . . H8 H -0.0027 0.4147 0.0319 0.052 Uiso 1 1 calc R . . C9 C 0.1259(2) 0.36209(15) 0.1828(4) 0.0423(7) Uani 1 1 d . . . H9 H 0.1602 0.4071 0.2289 0.051 Uiso 1 1 calc R . . C10 C 0.44995(18) 0.12869(14) 0.4639(3) 0.0322(6) Uani 1 1 d . . . C11 C 0.48445(18) 0.11475(14) 0.6406(3) 0.0330(6) Uani 1 1 d . . . C12 C 0.58870(18) 0.13253(14) 0.7212(3) 0.0339(6) Uani 1 1 d . . . H12 H 0.6139 0.1248 0.8420 0.041 Uiso 1 1 calc R . . C13 C 0.65649(19) 0.16117(14) 0.6300(3) 0.0352(6) Uani 1 1 d . . . C14 C 0.6190(2) 0.17283(15) 0.4541(4) 0.0411(7) Uani 1 1 d . . . H14 H 0.6655 0.1921 0.3910 0.049 Uiso 1 1 calc R . . C15 C 0.5158(2) 0.15722(15) 0.3674(3) 0.0385(6) Uani 1 1 d . . . C16 C 0.4126(2) 0.08311(19) 0.7426(4) 0.0480(8) Uani 1 1 d . . . H16A H 0.3625 0.1217 0.7574 0.072 Uiso 1 1 calc R . . H16B H 0.4546 0.0668 0.8561 0.072 Uiso 1 1 calc R . . H16C H 0.3740 0.0403 0.6806 0.072 Uiso 1 1 calc R . . C17 C 0.7694(2) 0.17968(17) 0.7191(4) 0.0468(7) Uani 1 1 d . . . H17A H 0.7807 0.1733 0.8441 0.070 Uiso 1 1 calc R . . H17B H 0.7843 0.2316 0.6938 0.070 Uiso 1 1 calc R . . H17C H 0.8166 0.1461 0.6772 0.070 Uiso 1 1 calc R . . C18 C 0.4777(3) 0.1712(2) 0.1750(4) 0.0615(9) Uani 1 1 d . . . H18A H 0.4301 0.1308 0.1214 0.092 Uiso 1 1 calc R . . H18B H 0.5383 0.1727 0.1242 0.092 Uiso 1 1 calc R . . H18C H 0.4402 0.2191 0.1549 0.092 Uiso 1 1 calc R . . N1 N 0.18007(15) 0.16661(12) 0.2269(3) 0.0327(5) Uani 1 1 d . . . N2 N 0.34040(16) 0.11383(12) 0.3757(3) 0.0338(5) Uani 1 1 d . . . N3 N 0.17409(16) 0.29709(12) 0.2360(3) 0.0372(5) Uani 1 1 d . . . F1 F 0.10984(17) -0.05505(19) 0.8780(4) 0.1209(11) Uani 1 1 d . . . F2 F 0.18493(16) -0.04619(11) 0.6554(2) 0.0689(6) Uani 1 1 d . . . F3 F 0.27251(14) -0.01552(11) 0.9262(2) 0.0608(6) Uani 1 1 d . . . F4 F 0.2336(2) -0.13549(12) 0.8519(3) 0.1015(9) Uani 1 1 d . . . B1 B 0.1999(2) -0.06318(17) 0.8270(4) 0.0356(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0347(13) 0.0274(13) 0.0322(13) 0.0002(11) 0.0039(10) -0.0023(10) C2 0.0440(14) 0.0324(15) 0.0414(16) -0.0054(12) 0.0039(12) -0.0135(12) C3 0.0583(17) 0.0291(15) 0.0453(17) -0.0033(12) 0.0070(13) -0.0138(12) C4 0.0552(16) 0.0236(13) 0.0401(15) -0.0041(11) 0.0039(12) -0.0023(12) C5 0.0292(12) 0.0343(14) 0.0306(13) -0.0002(11) 0.0063(10) -0.0023(10) C6 0.0316(13) 0.0450(17) 0.0418(16) -0.0054(13) 0.0039(11) -0.0047(11) C7 0.0278(12) 0.0555(19) 0.0440(16) 0.0014(14) 0.0031(11) 0.0055(12) C8 0.0349(14) 0.0436(17) 0.0507(17) 0.0064(13) 0.0109(12) 0.0077(12) C9 0.0365(14) 0.0311(15) 0.0574(18) 0.0025(13) 0.0084(13) -0.0001(11) C10 0.0357(13) 0.0246(13) 0.0339(14) -0.0023(11) 0.0045(10) 0.0022(10) C11 0.0337(13) 0.0307(14) 0.0353(14) 0.0023(11) 0.0100(10) 0.0069(10) C12 0.0331(13) 0.0335(14) 0.0338(14) 0.0036(11) 0.0060(10) 0.0070(11) C13 0.0337(13) 0.0269(13) 0.0460(16) 0.0022(11) 0.0118(11) 0.0070(10) C14 0.0443(15) 0.0367(15) 0.0459(17) 0.0053(13) 0.0179(13) -0.0013(12) C15 0.0494(15) 0.0327(14) 0.0333(14) 0.0011(11) 0.0104(12) -0.0018(12) C16 0.0416(15) 0.066(2) 0.0361(15) 0.0043(14) 0.0098(12) -0.0067(14) C17 0.0340(13) 0.0433(17) 0.0623(19) 0.0123(14) 0.0107(13) 0.0032(12) C18 0.079(2) 0.067(2) 0.0367(17) 0.0059(16) 0.0107(16) -0.0197(18) N1 0.0343(11) 0.0289(12) 0.0317(12) -0.0031(9) 0.0027(9) -0.0053(9) N2 0.0375(11) 0.0266(11) 0.0329(12) -0.0029(9) 0.0012(9) -0.0018(9) N3 0.0338(11) 0.0306(12) 0.0438(13) 0.0013(10) 0.0033(9) -0.0008(9) F1 0.0551(13) 0.170(3) 0.150(2) -0.056(2) 0.0472(14) -0.0314(15) F2 0.0969(15) 0.0563(12) 0.0394(10) 0.0060(9) -0.0089(10) -0.0191(10) F3 0.0671(12) 0.0682(13) 0.0421(10) -0.0068(9) 0.0044(8) -0.0285(10) F4 0.193(3) 0.0394(12) 0.0621(14) 0.0042(10) 0.0141(15) 0.0227(14) B1 0.0427(16) 0.0270(15) 0.0351(16) 0.0003(12) 0.0059(13) -0.0065(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N2 1.307(3) . ? C1 N1 1.327(3) . ? C2 N1 1.475(3) . ? C2 C3 1.512(4) . ? C3 C4 1.515(4) . ? C4 N2 1.477(3) . ? C5 N3 1.330(3) . ? C5 C6 1.382(3) . ? C5 N1 1.439(3) . ? C6 C7 1.385(4) . ? C7 C8 1.373(4) . ? C8 C9 1.379(4) . ? C9 N3 1.339(3) . ? C10 C15 1.392(4) . ? C10 C11 1.394(4) . ? C10 N2 1.456(3) . ? C11 C12 1.393(3) . ? C11 C16 1.504(4) . ? C12 C13 1.383(4) . ? C13 C14 1.384(4) . ? C13 C17 1.509(4) . ? C14 C15 1.385(4) . ? C15 C18 1.514(4) . ? F1 B1 1.352(4) . ? F2 B1 1.371(3) . ? F3 B1 1.371(3) . ? F4 B1 1.364(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C1 N1 125.1(2) . . ? N1 C2 C3 110.0(2) . . ? C2 C3 C4 111.6(2) . . ? N2 C4 C3 108.7(2) . . ? N3 C5 C6 124.1(2) . . ? N3 C5 N1 114.9(2) . . ? C6 C5 N1 121.0(2) . . ? C5 C6 C7 117.4(3) . . ? C8 C7 C6 120.0(2) . . ? C7 C8 C9 117.9(3) . . ? N3 C9 C8 123.7(3) . . ? C15 C10 C11 122.7(2) . . ? C15 C10 N2 118.2(2) . . ? C11 C10 N2 119.1(2) . . ? C12 C11 C10 117.2(2) . . ? C12 C11 C16 120.7(2) . . ? C10 C11 C16 122.0(2) . . ? C13 C12 C11 121.8(2) . . ? C12 C13 C14 118.8(2) . . ? C12 C13 C17 121.1(2) . . ? C14 C13 C17 120.1(2) . . ? C13 C14 C15 122.0(2) . . ? C14 C15 C10 117.4(2) . . ? C14 C15 C18 120.3(2) . . ? C10 C15 C18 122.2(2) . . ? C1 N1 C5 118.6(2) . . ? C1 N1 C2 120.2(2) . . ? C5 N1 C2 120.96(19) . . ? C1 N2 C10 118.2(2) . . ? C1 N2 C4 121.1(2) . . ? C10 N2 C4 119.94(19) . . ? C5 N3 C9 116.8(2) . . ? F1 B1 F4 109.5(3) . . ? F1 B1 F3 106.9(3) . . ? F4 B1 F3 110.6(3) . . ? F1 B1 F2 111.3(3) . . ? F4 B1 F2 108.4(2) . . ? F3 B1 F2 110.2(2) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.465 _refine_diff_density_min -0.348 _refine_diff_density_rms 0.066 # Attachment 'kjc0727.cif' data_kjc0727 _database_code_depnum_ccdc_archive 'CCDC 733089' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H21 Br N2 O2, Br1, H2O' _chemical_formula_sum 'C18 H23 Br N2 O3' _chemical_formula_weight 395.29 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 0.0000 0.0000 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.50160(10) _cell_length_b 10.2088(2) _cell_length_c 13.3104(3) _cell_angle_alpha 71.6920(10) _cell_angle_beta 82.8260(10) _cell_angle_gamma 74.2070(10) _cell_volume 930.35(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4724 _cell_measurement_theta_min 3.06 _cell_measurement_theta_max 30.24 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.411 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 2.227 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5095 _exptl_absorpt_correction_T_max 0.7760 _exptl_absorpt_process_details Denzo _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'CCD scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16175 _diffrn_reflns_av_R_equivalents 0.1078 _diffrn_reflns_av_sigmaI/netI 0.0734 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.06 _diffrn_reflns_theta_max 30.24 _reflns_number_total 5426 _reflns_number_gt 4724 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'cOLLECT,Nonius BV, 1997-2001' _computing_cell_refinement DENZO/SCALEPACK _computing_data_reduction DENZO/SCALEPACK _computing_structure_solution SHELXs-97 _computing_structure_refinement SHELXL-97 _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^)+(0.0268P)^2^+0.4315P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5426 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0472 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.1052 _refine_ls_wR_factor_gt 0.1004 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0879(2) 0.16339(19) 0.75658(14) 0.0203(3) Uani 1 1 d . . . H1 H 0.0125 0.1741 0.8177 0.024 Uiso 1 1 calc R . . C2 C 0.3439(3) 0.0241(2) 0.67473(15) 0.0268(4) Uani 1 1 d . . . H2A H 0.2909 -0.0327 0.6438 0.032 Uiso 1 1 calc R . . H2B H 0.4713 -0.0301 0.6958 0.032 Uiso 1 1 calc R . . C3 C 0.3487(3) 0.1658(3) 0.59367(17) 0.0357(5) Uani 1 1 d . . . H3A H 0.4171 0.1491 0.5284 0.043 Uiso 1 1 calc R . . H3B H 0.4154 0.2171 0.6220 0.043 Uiso 1 1 calc R . . C4 C 0.1534(3) 0.2569(2) 0.56693(15) 0.0306(4) Uani 1 1 d . . . H4A H 0.1583 0.3544 0.5234 0.037 Uiso 1 1 calc R . . H4B H 0.0944 0.2156 0.5259 0.037 Uiso 1 1 calc R . . C5 C 0.2608(2) -0.0511(2) 0.87043(14) 0.0213(3) Uani 1 1 d . . . C6 C 0.2628(2) -0.0061(2) 0.95934(14) 0.0230(4) Uani 1 1 d . . . C7 C 0.2984(3) -0.1077(2) 1.05799(16) 0.0293(4) Uani 1 1 d . . . H7 H 0.2999 -0.0785 1.1190 0.035 Uiso 1 1 calc R . . C8 C 0.3316(3) -0.2515(2) 1.06665(17) 0.0339(5) Uani 1 1 d . . . H8 H 0.3560 -0.3203 1.1338 0.041 Uiso 1 1 calc R . . C9 C 0.3295(3) -0.2959(2) 0.97861(18) 0.0333(5) Uani 1 1 d . . . H9 H 0.3521 -0.3944 0.9855 0.040 Uiso 1 1 calc R . . C10 C 0.2941(3) -0.1953(2) 0.88005(17) 0.0274(4) Uani 1 1 d . . . H10 H 0.2926 -0.2251 0.8194 0.033 Uiso 1 1 calc R . . C11 C 0.2203(3) 0.1877(2) 1.03154(17) 0.0313(4) Uani 1 1 d . . . H11A H 0.1198 0.1588 1.0807 0.047 Uiso 1 1 calc R . . H11B H 0.1956 0.2918 1.0080 0.047 Uiso 1 1 calc R . . H11C H 0.3380 0.1474 1.0674 0.047 Uiso 1 1 calc R . . C12 C -0.1105(2) 0.38132(19) 0.66698(13) 0.0195(3) Uani 1 1 d . . . C13 C -0.0901(3) 0.4833(2) 0.71093(14) 0.0230(4) Uani 1 1 d . . . C14 C -0.2395(3) 0.5998(2) 0.71254(16) 0.0281(4) Uani 1 1 d . . . H14 H -0.2278 0.6708 0.7417 0.034 Uiso 1 1 calc R . . C15 C -0.4053(3) 0.6103(2) 0.67099(15) 0.0285(4) Uani 1 1 d . . . H15 H -0.5072 0.6890 0.6723 0.034 Uiso 1 1 calc R . . C16 C -0.4254(3) 0.5089(2) 0.62774(16) 0.0288(4) Uani 1 1 d . . . H16 H -0.5403 0.5179 0.6000 0.035 Uiso 1 1 calc R . . C17 C -0.2767(3) 0.3933(2) 0.62489(15) 0.0255(4) Uani 1 1 d . . . H17 H -0.2887 0.3236 0.5946 0.031 Uiso 1 1 calc R . . C18 C 0.1050(4) 0.5561(3) 0.8000(2) 0.0403(5) Uani 1 1 d . . . H18A H 0.0877 0.6511 0.7489 0.061 Uiso 1 1 calc R . . H18B H 0.2306 0.5249 0.8263 0.061 Uiso 1 1 calc R . . H18C H 0.0142 0.5592 0.8594 0.061 Uiso 1 1 calc R . . N1 N 0.2288(2) 0.05066(16) 0.76833(12) 0.0203(3) Uani 1 1 d . . . N2 N 0.0444(2) 0.26191(16) 0.66644(12) 0.0198(3) Uani 1 1 d . . . O1 O 0.2314(2) 0.13657(15) 0.94172(11) 0.0280(3) Uani 1 1 d . . . O2 O 0.0798(2) 0.45867(17) 0.74972(13) 0.0328(3) Uani 1 1 d . . . O3 O -0.2029(3) 0.1897(2) 0.44292(16) 0.0465(5) Uani 1 1 d . . . Br1 Br -0.15590(3) -0.03311(2) 0.686300(16) 0.03190(8) Uani 1 1 d . . . H2O H -0.197(4) 0.135(3) 0.498(2) 0.041(8) Uiso 1 1 d . . . H1O H -0.104(5) 0.153(4) 0.412(3) 0.053(9) 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 0.0181(7) 0.0201(8) 0.0221(8) -0.0070(7) 0.0002(6) -0.0035(6) C2 0.0235(9) 0.0282(10) 0.0244(9) -0.0092(8) 0.0024(7) 0.0004(7) C3 0.0249(9) 0.0373(12) 0.0311(10) -0.0006(9) 0.0081(8) -0.0002(8) C4 0.0277(9) 0.0346(11) 0.0204(8) -0.0048(8) 0.0039(7) 0.0011(8) C5 0.0164(7) 0.0211(8) 0.0235(8) -0.0039(7) -0.0006(6) -0.0031(6) C6 0.0199(8) 0.0230(8) 0.0228(8) -0.0044(7) 0.0004(6) -0.0033(7) C7 0.0252(9) 0.0327(10) 0.0231(9) -0.0018(8) 0.0018(7) -0.0045(8) C8 0.0273(10) 0.0297(10) 0.0316(10) 0.0052(9) 0.0011(8) -0.0032(8) C9 0.0294(10) 0.0203(9) 0.0420(12) -0.0008(9) -0.0005(9) -0.0031(8) C10 0.0248(9) 0.0232(9) 0.0324(10) -0.0080(8) -0.0003(8) -0.0039(7) C11 0.0330(10) 0.0340(11) 0.0283(9) -0.0137(9) 0.0004(8) -0.0058(8) C12 0.0210(8) 0.0168(7) 0.0183(7) -0.0044(6) -0.0004(6) -0.0019(6) C13 0.0260(9) 0.0200(8) 0.0224(8) -0.0057(7) -0.0028(7) -0.0047(7) C14 0.0364(10) 0.0203(9) 0.0258(9) -0.0082(7) -0.0009(8) -0.0029(8) C15 0.0296(10) 0.0241(9) 0.0236(8) -0.0054(7) 0.0016(7) 0.0036(7) C16 0.0224(9) 0.0320(10) 0.0293(9) -0.0094(8) -0.0043(7) -0.0005(8) C17 0.0244(9) 0.0257(9) 0.0270(9) -0.0102(8) -0.0040(7) -0.0030(7) C18 0.0503(13) 0.0310(11) 0.0482(13) -0.0159(10) -0.0154(11) -0.0128(10) N1 0.0189(7) 0.0186(7) 0.0212(7) -0.0051(6) -0.0005(5) -0.0018(5) N2 0.0201(7) 0.0183(7) 0.0196(7) -0.0056(6) 0.0003(5) -0.0028(5) O1 0.0377(8) 0.0229(7) 0.0232(6) -0.0064(5) -0.0044(6) -0.0063(6) O2 0.0313(7) 0.0282(7) 0.0453(8) -0.0164(7) -0.0117(7) -0.0066(6) O3 0.0472(11) 0.0454(11) 0.0368(9) -0.0130(9) -0.0061(8) 0.0080(8) Br1 0.03142(12) 0.03147(12) 0.03309(12) -0.00874(9) 0.00106(8) -0.01016(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 N2 1.311(2) . ? C1 N1 1.316(2) . ? C2 N1 1.479(2) . ? C2 C3 1.515(3) . ? C3 C4 1.523(3) . ? C4 N2 1.475(2) . ? C5 C10 1.392(3) . ? C5 C6 1.400(3) . ? C5 N1 1.429(2) . ? C6 O1 1.358(2) . ? C6 C7 1.397(3) . ? C7 C8 1.391(3) . ? C8 C9 1.386(4) . ? C9 C10 1.392(3) . ? C11 O1 1.432(3) . ? C12 C17 1.390(3) . ? C12 C13 1.393(3) . ? C12 N2 1.438(2) . ? C13 O2 1.365(2) . ? C13 C14 1.398(3) . ? C14 C15 1.388(3) . ? C15 C16 1.381(3) . ? C16 C17 1.392(3) . ? C18 O2 1.423(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C1 N1 124.64(16) . . ? N1 C2 C3 108.87(17) . . ? C2 C3 C4 111.01(17) . . ? N2 C4 C3 108.76(16) . . ? C10 C5 C6 120.46(17) . . ? C10 C5 N1 119.26(18) . . ? C6 C5 N1 120.27(17) . . ? O1 C6 C7 124.63(19) . . ? O1 C6 C5 116.10(16) . . ? C7 C6 C5 119.27(19) . . ? C8 C7 C6 119.8(2) . . ? C9 C8 C7 120.89(19) . . ? C8 C9 C10 119.7(2) . . ? C5 C10 C9 119.9(2) . . ? C17 C12 C13 121.14(17) . . ? C17 C12 N2 120.27(17) . . ? C13 C12 N2 118.59(16) . . ? O2 C13 C12 115.25(16) . . ? O2 C13 C14 125.39(19) . . ? C12 C13 C14 119.37(17) . . ? C15 C14 C13 119.0(2) . . ? C16 C15 C14 121.53(18) . . ? C15 C16 C17 119.77(19) . . ? C12 C17 C16 119.16(19) . . ? C1 N1 C5 119.62(15) . . ? C1 N1 C2 119.91(15) . . ? C5 N1 C2 120.30(15) . . ? C1 N2 C12 118.08(15) . . ? C1 N2 C4 122.23(16) . . ? C12 N2 C4 119.63(15) . . ? C6 O1 C11 117.84(16) . . ? C13 O2 C18 117.47(18) . . ? _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 30.24 _diffrn_measured_fraction_theta_full 0.977 _refine_diff_density_max 0.565 _refine_diff_density_min -0.760 _refine_diff_density_rms 0.079 # Attachment 'kjc0729.cif' data_kjc0729 _database_code_depnum_ccdc_archive 'CCDC 733090' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H23 N2 O2, I' _chemical_formula_sum 'C19 H23 I N2 O2' _chemical_formula_weight 438.29 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 0.0000 0.0000 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.89000(10) _cell_length_b 10.2100(2) _cell_length_c 12.9030(3) _cell_angle_alpha 106.1680(10) _cell_angle_beta 94.4780(10) _cell_angle_gamma 104.8850(10) _cell_volume 952.20(3) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 3551 _cell_measurement_theta_min 1.66 _cell_measurement_theta_max 27.49 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.529 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 1.694 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7281 _exptl_absorpt_correction_T_max 0.9353 _exptl_absorpt_process_details Denzo _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8036 _diffrn_reflns_av_R_equivalents 0.0349 _diffrn_reflns_av_sigmaI/netI 0.0485 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4344 _reflns_number_gt 3551 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'cOLLECT,Nonius BV, 1997-2001' _computing_cell_refinement DENZO/SCALEPACK _computing_data_reduction DENZO/SCALEPACK _computing_structure_solution SHELXs-97 _computing_structure_refinement SHELXL-97 _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^)+(0.0907P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4344 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0538 _refine_ls_R_factor_gt 0.0370 _refine_ls_wR_factor_ref 0.1405 _refine_ls_wR_factor_gt 0.1104 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C9 C 0.6023(9) 0.1026(6) -0.1950(5) 0.0684(16) Uani 1 1 d . . . H9 H 0.6392 0.0593 -0.2591 0.082 Uiso 1 1 calc R . . C1 C 0.4881(5) 0.2810(4) 0.1828(3) 0.0336(8) Uani 1 1 d . . . H1 H 0.5545 0.2167 0.1762 0.040 Uiso 1 1 calc R . . C2 C 0.3400(6) 0.4085(5) 0.0827(3) 0.0427(9) Uani 1 1 d . . . H2A H 0.3150 0.4025 0.0064 0.051 Uiso 1 1 calc R . . H2B H 0.4169 0.5036 0.1217 0.051 Uiso 1 1 calc R . . C3 C 0.1682(6) 0.3867(6) 0.1280(4) 0.0517(11) Uani 1 1 d . . . H3A H 0.0929 0.2912 0.0889 0.062 Uiso 1 1 calc R . . H3B H 0.1086 0.4528 0.1124 0.062 Uiso 1 1 calc R . . C4 C 0.1823(6) 0.4058(6) 0.2503(4) 0.0501(11) Uani 1 1 d . . . H4A H 0.1253 0.4775 0.2827 0.060 Uiso 1 1 calc R . . H4B H 0.1155 0.3169 0.2595 0.060 Uiso 1 1 calc R . . C5 C 0.3677(5) 0.4487(4) 0.3136(3) 0.0381(9) Uani 1 1 d . . . H5A H 0.4374 0.5351 0.3021 0.046 Uiso 1 1 calc R . . H5B H 0.3608 0.4697 0.3910 0.046 Uiso 1 1 calc R . . C6 C 0.4947(5) 0.2311(4) -0.0069(3) 0.0374(8) Uani 1 1 d . . . C7 C 0.3683(6) 0.1244(4) -0.0891(3) 0.0419(9) Uani 1 1 d . . . C8 C 0.4242(8) 0.0601(5) -0.1853(4) 0.0565(12) Uani 1 1 d . . . H8 H 0.3429 -0.0106 -0.2422 0.068 Uiso 1 1 calc R . . C10 C 0.7244(8) 0.2058(6) -0.1135(5) 0.0665(15) Uani 1 1 d . . . H10 H 0.8432 0.2317 -0.1219 0.080 Uiso 1 1 calc R . . C11 C 0.6709(7) 0.2729(5) -0.0173(4) 0.0513(11) Uani 1 1 d . . . H11 H 0.7529 0.3444 0.0388 0.062 Uiso 1 1 calc R . . C12 C 0.0643(8) -0.0076(6) -0.1514(6) 0.0798(18) Uani 1 1 d . . . H12A H 0.0525 0.0303 -0.2109 0.120 Uiso 1 1 calc R . . H12B H -0.0462 -0.0256 -0.1239 0.120 Uiso 1 1 calc R . . H12C H 0.0947 -0.0951 -0.1766 0.120 Uiso 1 1 calc R . . C13 C 0.5472(5) 0.3027(4) 0.3685(3) 0.0375(8) Uani 1 1 d . . . C14 C 0.4414(6) 0.2263(4) 0.4271(3) 0.0401(9) Uani 1 1 d . . . C15 C 0.5259(8) 0.1951(5) 0.5122(4) 0.0534(12) Uani 1 1 d . . . H15 H 0.4590 0.1449 0.5525 0.064 Uiso 1 1 calc R . . C16 C 0.7088(8) 0.2386(5) 0.5364(4) 0.0605(13) Uani 1 1 d . . . H16 H 0.7637 0.2168 0.5933 0.073 Uiso 1 1 calc R . . C17 C 0.8117(7) 0.3128(5) 0.4794(4) 0.0555(12) Uani 1 1 d . . . H17 H 0.9349 0.3408 0.4969 0.067 Uiso 1 1 calc R . . C18 C 0.7295(6) 0.3461(5) 0.3940(4) 0.0454(10) Uani 1 1 d . . . H18 H 0.7977 0.3973 0.3548 0.055 Uiso 1 1 calc R . . C19 C 0.1491(7) 0.1067(6) 0.4491(4) 0.0597(13) Uani 1 1 d . . . H19A H 0.1784 0.0195 0.4432 0.090 Uiso 1 1 calc R . . H19B H 0.0278 0.0852 0.4162 0.090 Uiso 1 1 calc R . . H19C H 0.1646 0.1610 0.5248 0.090 Uiso 1 1 calc R . . N1 N 0.4359(4) 0.3023(3) 0.0913(2) 0.0341(7) Uani 1 1 d . . . N2 N 0.4601(4) 0.3373(3) 0.2819(3) 0.0340(7) Uani 1 1 d . . . O1 O 0.2000(5) 0.0921(4) -0.0667(3) 0.0550(8) Uani 1 1 d . . . O2 O 0.2637(4) 0.1879(4) 0.3938(3) 0.0513(7) Uani 1 1 d . . . I1 I 0.83691(3) 0.64885(3) 0.24322(2) 0.04798(14) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C9 0.104(5) 0.065(3) 0.049(3) 0.017(3) 0.039(3) 0.041(4) C1 0.0369(19) 0.0330(19) 0.0325(19) 0.0096(15) 0.0073(15) 0.0132(15) C2 0.052(2) 0.047(2) 0.038(2) 0.0174(18) 0.0064(18) 0.025(2) C3 0.042(2) 0.065(3) 0.048(3) 0.011(2) 0.0040(19) 0.026(2) C4 0.038(2) 0.062(3) 0.051(3) 0.015(2) 0.0093(19) 0.018(2) C5 0.043(2) 0.037(2) 0.034(2) 0.0060(16) 0.0061(16) 0.0164(17) C6 0.046(2) 0.037(2) 0.0312(19) 0.0098(16) 0.0093(16) 0.0170(18) C7 0.053(2) 0.033(2) 0.039(2) 0.0119(17) 0.0064(18) 0.0099(18) C8 0.087(4) 0.041(2) 0.039(2) 0.0043(19) 0.009(2) 0.023(2) C10 0.073(3) 0.072(4) 0.067(3) 0.023(3) 0.041(3) 0.031(3) C11 0.052(2) 0.048(3) 0.053(3) 0.010(2) 0.017(2) 0.016(2) C12 0.070(4) 0.051(3) 0.084(4) -0.003(3) -0.011(3) -0.008(3) C13 0.045(2) 0.037(2) 0.0291(19) 0.0065(16) 0.0028(16) 0.0147(17) C14 0.056(2) 0.033(2) 0.033(2) 0.0092(16) 0.0103(17) 0.0152(18) C15 0.085(4) 0.038(2) 0.038(2) 0.0144(19) 0.006(2) 0.017(2) C16 0.085(4) 0.052(3) 0.047(3) 0.014(2) -0.012(2) 0.030(3) C17 0.056(3) 0.050(3) 0.059(3) 0.014(2) -0.006(2) 0.021(2) C18 0.044(2) 0.045(2) 0.045(2) 0.013(2) 0.0000(19) 0.0123(19) C19 0.067(3) 0.054(3) 0.057(3) 0.022(2) 0.026(3) 0.005(2) N1 0.0387(17) 0.0361(17) 0.0274(15) 0.0057(13) 0.0053(13) 0.0155(14) N2 0.0392(17) 0.0351(16) 0.0310(16) 0.0116(13) 0.0076(13) 0.0141(14) O1 0.0498(18) 0.0495(19) 0.0512(19) 0.0077(15) 0.0001(15) 0.0004(15) O2 0.0529(18) 0.0540(19) 0.0468(17) 0.0219(15) 0.0125(14) 0.0068(15) I1 0.04325(19) 0.0526(2) 0.0460(2) 0.01732(15) 0.00377(13) 0.00925(14) _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 C9 C10 1.359(9) . ? C9 C8 1.387(9) . ? C1 N2 1.310(5) . ? C1 N1 1.312(5) . ? C2 N1 1.496(5) . ? C2 C3 1.506(6) . ? C3 C4 1.526(6) . ? C4 C5 1.511(6) . ? C5 N2 1.485(5) . ? C6 C11 1.375(6) . ? C6 C7 1.392(6) . ? C6 N1 1.450(5) . ? C7 O1 1.358(5) . ? C7 C8 1.395(6) . ? C10 C11 1.395(7) . ? C12 O1 1.419(6) . ? C13 C18 1.375(6) . ? C13 C14 1.404(6) . ? C13 N2 1.438(5) . ? C14 O2 1.354(5) . ? C14 C15 1.393(6) . ? C15 C16 1.379(8) . ? C16 C17 1.365(8) . ? C17 C18 1.400(6) . ? C19 O2 1.435(5) . ? 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 C10 C9 C8 121.9(5) . . ? N2 C1 N1 129.3(3) . . ? N1 C2 C3 113.4(3) . . ? C2 C3 C4 116.6(4) . . ? C5 C4 C3 116.5(4) . . ? N2 C5 C4 113.3(4) . . ? C11 C6 C7 122.2(4) . . ? C11 C6 N1 119.4(4) . . ? C7 C6 N1 118.3(4) . . ? O1 C7 C6 115.9(4) . . ? O1 C7 C8 126.0(4) . . ? C6 C7 C8 118.2(4) . . ? C9 C8 C7 119.3(5) . . ? C9 C10 C11 119.8(5) . . ? C6 C11 C10 118.7(5) . . ? C18 C13 C14 121.2(4) . . ? C18 C13 N2 120.5(4) . . ? C14 C13 N2 118.3(4) . . ? O2 C14 C15 125.9(4) . . ? O2 C14 C13 115.9(3) . . ? C15 C14 C13 118.3(4) . . ? C16 C15 C14 119.9(5) . . ? C17 C16 C15 121.8(4) . . ? C16 C17 C18 119.2(5) . . ? C13 C18 C17 119.6(4) . . ? C1 N1 C6 117.6(3) . . ? C1 N1 C2 125.0(3) . . ? C6 N1 C2 116.9(3) . . ? C1 N2 C13 116.8(3) . . ? C1 N2 C5 125.1(3) . . ? C13 N2 C5 117.4(3) . . ? C7 O1 C12 117.7(4) . . ? C14 O2 C19 118.3(4) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.460 _refine_diff_density_min -0.666 _refine_diff_density_rms 0.152 # Attachment 'kjc0737.cif' data_kjc0737 _database_code_depnum_ccdc_archive 'CCDC 733091' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H25 N2 O, Br1' _chemical_formula_sum 'C20 H25 Br N2 O' _chemical_formula_weight 389.33 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 0.0000 0.0000 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 8.11730(10) _cell_length_b 16.0772(3) _cell_length_c 14.2610(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.7060(10) _cell_angle_gamma 90.00 _cell_volume 1834.47(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3435 _cell_measurement_theta_min 2.92 _cell_measurement_theta_max 27.45 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.410 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 2.250 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7290 _exptl_absorpt_correction_T_max 0.8063 _exptl_absorpt_process_details Denzo _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29436 _diffrn_reflns_av_R_equivalents 0.1035 _diffrn_reflns_av_sigmaI/netI 0.0519 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 27.45 _reflns_number_total 4195 _reflns_number_gt 3435 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'cOLLECT,Nonius BV, 1997-2001' _computing_cell_refinement DENZO/SCALEPACK _computing_data_reduction DENZO/SCALEPACK _computing_structure_solution SHELXs-97 _computing_structure_refinement SHELXL-97 _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^)+(0.0312P)^2^+2.2513P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4195 _refine_ls_number_parameters 221 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0566 _refine_ls_R_factor_gt 0.0420 _refine_ls_wR_factor_ref 0.0995 _refine_ls_wR_factor_gt 0.0927 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7220(3) 0.02832(14) 0.28210(17) 0.0161(5) Uani 1 1 d . . . H1 H 0.8011 -0.0109 0.3125 0.019 Uiso 1 1 calc R . . C2 C 0.5938(3) 0.16497(16) 0.27938(19) 0.0237(6) Uani 1 1 d . . . H2A H 0.6402 0.2207 0.2978 0.028 Uiso 1 1 calc R . . H2B H 0.4839 0.1601 0.3003 0.028 Uiso 1 1 calc R . . C3 C 0.5726(4) 0.15490(16) 0.1729(2) 0.0291(6) Uani 1 1 d . . . H3A H 0.6801 0.1659 0.1511 0.035 Uiso 1 1 calc R . . H3B H 0.4891 0.1953 0.1414 0.035 Uiso 1 1 calc R . . C4 C 0.5148(3) 0.06706(16) 0.1462(2) 0.0254(6) Uani 1 1 d . . . H4A H 0.4019 0.0580 0.1618 0.030 Uiso 1 1 calc R . . H4B H 0.5092 0.0585 0.0770 0.030 Uiso 1 1 calc R . . C5 C 0.8030(3) 0.11383(15) 0.41851(19) 0.0194(5) Uani 1 1 d . . . C6 C 0.7938(3) 0.05735(15) 0.49282(18) 0.0193(5) Uani 1 1 d . . . C7 C 0.8838(3) 0.07263(17) 0.58279(19) 0.0238(6) Uani 1 1 d . . . H7 H 0.8778 0.0350 0.6334 0.029 Uiso 1 1 calc R . . C8 C 0.9829(4) 0.14369(18) 0.5983(2) 0.0292(6) Uani 1 1 d . . . H8 H 1.0448 0.1542 0.6599 0.035 Uiso 1 1 calc R . . C9 C 0.9924(4) 0.19899(18) 0.5254(2) 0.0319(7) Uani 1 1 d . . . H9 H 1.0604 0.2472 0.5370 0.038 Uiso 1 1 calc R . . C10 C 0.9028(4) 0.18434(16) 0.4352(2) 0.0263(6) Uani 1 1 d . . . H10 H 0.9096 0.2224 0.3850 0.032 Uiso 1 1 calc R . . C11 C 0.6797(4) -0.06817(17) 0.5442(2) 0.0283(6) Uani 1 1 d . . . H11A H 0.7904 -0.0906 0.5698 0.042 Uiso 1 1 calc R . . H11B H 0.6050 -0.1138 0.5190 0.042 Uiso 1 1 calc R . . H11C H 0.6340 -0.0397 0.5950 0.042 Uiso 1 1 calc R . . C12 C 0.6446(3) -0.07605(14) 0.16367(17) 0.0157(5) Uani 1 1 d . . . C13 C 0.7267(3) -0.08935(15) 0.08648(18) 0.0176(5) Uani 1 1 d . . . C14 C 0.7306(3) -0.16968(15) 0.05123(19) 0.0202(5) Uani 1 1 d . . . H14 H 0.7827 -0.1794 -0.0026 0.024 Uiso 1 1 calc R . . C15 C 0.6601(3) -0.23675(15) 0.09280(19) 0.0210(5) Uani 1 1 d . . . C16 C 0.5805(3) -0.22057(16) 0.16926(19) 0.0231(6) Uani 1 1 d . . . H16 H 0.5329 -0.2657 0.1983 0.028 Uiso 1 1 calc R . . C17 C 0.5674(3) -0.14081(16) 0.20543(18) 0.0194(5) Uani 1 1 d . . . C18 C 0.8106(3) -0.01967(16) 0.0421(2) 0.0256(6) Uani 1 1 d . . . H18A H 0.8642 -0.0418 -0.0093 0.038 Uiso 1 1 calc R . . H18B H 0.8952 0.0062 0.0904 0.038 Uiso 1 1 calc R . . H18C H 0.7270 0.0220 0.0162 0.038 Uiso 1 1 calc R . . C19 C 0.6701(4) -0.32308(16) 0.0528(2) 0.0299(6) Uani 1 1 d . . . H19A H 0.6322 -0.3637 0.0959 0.045 Uiso 1 1 calc R . . H19B H 0.7860 -0.3353 0.0464 0.045 Uiso 1 1 calc R . . H19C H 0.5987 -0.3264 -0.0097 0.045 Uiso 1 1 calc R . . C20 C 0.4672(4) -0.12509(19) 0.2834(2) 0.0341(7) Uani 1 1 d . . . H20A H 0.5432 -0.1145 0.3432 0.051 Uiso 1 1 calc R . . H20B H 0.3983 -0.1739 0.2907 0.051 Uiso 1 1 calc R . . H20C H 0.3949 -0.0766 0.2670 0.051 Uiso 1 1 calc R . . N1 N 0.7085(3) 0.09984(12) 0.32599(15) 0.0176(4) Uani 1 1 d . . . N2 N 0.6344(2) 0.00763(12) 0.19977(15) 0.0167(4) Uani 1 1 d . . . O1 O 0.6936(2) -0.01009(11) 0.46920(13) 0.0229(4) Uani 1 1 d . . . Br1 Br 1.10330(3) 0.110452(17) 0.22029(2) 0.02853(10) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0181(11) 0.0158(11) 0.0149(12) 0.0004(9) 0.0038(10) 0.0010(9) C2 0.0340(14) 0.0156(12) 0.0214(14) -0.0003(10) 0.0043(12) 0.0074(11) C3 0.0474(17) 0.0193(14) 0.0198(15) 0.0035(11) 0.0028(13) 0.0117(12) C4 0.0298(14) 0.0251(14) 0.0186(14) 0.0014(11) -0.0035(11) 0.0123(11) C5 0.0216(12) 0.0185(12) 0.0186(13) -0.0039(10) 0.0050(10) 0.0022(10) C6 0.0181(12) 0.0218(12) 0.0182(13) -0.0043(10) 0.0040(10) 0.0016(10) C7 0.0247(13) 0.0299(14) 0.0167(13) -0.0014(11) 0.0036(11) 0.0057(11) C8 0.0302(14) 0.0327(15) 0.0226(15) -0.0124(12) -0.0013(12) 0.0031(12) C9 0.0366(16) 0.0265(14) 0.0321(17) -0.0123(12) 0.0043(13) -0.0072(12) C10 0.0362(15) 0.0194(13) 0.0247(15) -0.0043(11) 0.0092(12) -0.0044(11) C11 0.0352(15) 0.0290(14) 0.0203(14) 0.0086(12) 0.0036(12) -0.0027(12) C12 0.0157(11) 0.0151(11) 0.0148(12) -0.0014(9) -0.0020(10) 0.0010(9) C13 0.0161(11) 0.0189(12) 0.0170(13) -0.0006(10) 0.0004(10) -0.0001(9) C14 0.0172(11) 0.0214(12) 0.0218(13) -0.0066(11) 0.0025(10) 0.0007(10) C15 0.0189(12) 0.0175(12) 0.0239(14) -0.0036(10) -0.0046(10) 0.0022(10) C16 0.0276(13) 0.0197(13) 0.0199(14) 0.0022(10) -0.0020(11) -0.0062(10) C17 0.0215(12) 0.0230(12) 0.0127(12) -0.0007(10) -0.0003(10) -0.0048(10) C18 0.0298(14) 0.0261(14) 0.0229(14) -0.0055(11) 0.0103(12) -0.0098(11) C19 0.0293(14) 0.0186(13) 0.0394(18) -0.0080(12) -0.0016(13) 0.0009(11) C20 0.0442(17) 0.0379(17) 0.0235(16) -0.0063(13) 0.0149(14) -0.0164(14) N1 0.0239(11) 0.0155(10) 0.0138(11) 0.0009(8) 0.0041(9) 0.0022(8) N2 0.0202(10) 0.0155(10) 0.0145(10) 0.0003(8) 0.0028(8) 0.0035(8) O1 0.0281(9) 0.0230(9) 0.0166(9) 0.0047(7) 0.0006(8) -0.0049(7) Br1 0.03006(16) 0.03348(17) 0.02140(16) -0.00280(12) 0.00247(11) -0.00013(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N2 1.309(3) . ? C1 N1 1.323(3) . ? C2 N1 1.482(3) . ? C2 C3 1.508(4) . ? C3 C4 1.516(4) . ? C4 N2 1.479(3) . ? C5 C10 1.390(4) . ? C5 C6 1.407(4) . ? C5 N1 1.428(3) . ? C6 O1 1.363(3) . ? C6 C7 1.387(4) . ? C7 C8 1.393(4) . ? C8 C9 1.380(4) . ? C9 C10 1.387(4) . ? C11 O1 1.439(3) . ? C12 C13 1.396(3) . ? C12 C17 1.399(3) . ? C12 N2 1.448(3) . ? C13 C14 1.388(3) . ? C13 C18 1.505(3) . ? C14 C15 1.399(4) . ? C15 C16 1.382(4) . ? C15 C19 1.508(3) . ? C16 C17 1.393(4) . ? C17 C20 1.505(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C1 N1 124.7(2) . . ? N1 C2 C3 109.4(2) . . ? C2 C3 C4 109.3(2) . . ? N2 C4 C3 108.9(2) . . ? C10 C5 C6 120.0(3) . . ? C10 C5 N1 119.6(2) . . ? C6 C5 N1 120.4(2) . . ? O1 C6 C7 124.7(2) . . ? O1 C6 C5 115.6(2) . . ? C7 C6 C5 119.7(2) . . ? C6 C7 C8 119.5(3) . . ? C9 C8 C7 120.8(3) . . ? C8 C9 C10 120.2(3) . . ? C9 C10 C5 119.8(3) . . ? C13 C12 C17 122.0(2) . . ? C13 C12 N2 119.1(2) . . ? C17 C12 N2 118.9(2) . . ? C14 C13 C12 118.1(2) . . ? C14 C13 C18 120.0(2) . . ? C12 C13 C18 121.9(2) . . ? C13 C14 C15 121.8(2) . . ? C16 C15 C14 117.9(2) . . ? C16 C15 C19 122.3(2) . . ? C14 C15 C19 119.8(2) . . ? C15 C16 C17 122.7(2) . . ? C16 C17 C12 117.4(2) . . ? C16 C17 C20 120.9(2) . . ? C12 C17 C20 121.7(2) . . ? C1 N1 C5 120.0(2) . . ? C1 N1 C2 119.9(2) . . ? C5 N1 C2 120.14(19) . . ? C1 N2 C12 120.0(2) . . ? C1 N2 C4 120.6(2) . . ? C12 N2 C4 119.3(2) . . ? C6 O1 C11 116.8(2) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.316 _refine_diff_density_min -0.608 _refine_diff_density_rms 0.084 # Attachment 'kjc0746.cif' data_kjc0746 _database_code_depnum_ccdc_archive 'CCDC 733092' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H38 Cl N2 O Rh' _chemical_formula_sum 'C29 H38 Cl N2 O Rh' _chemical_formula_weight 568.97 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 0.0000 0.0000 '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 0.0060 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.34140(10) _cell_length_b 18.7565(2) _cell_length_c 15.3054(2) _cell_angle_alpha 90.00 _cell_angle_beta 104.9340(10) _cell_angle_gamma 90.00 _cell_volume 2591.11(5) _cell_formula_units_Z 4 _cell_measurement_temperature 274(2) _cell_measurement_reflns_used 4998 _cell_measurement_theta_min 1.75 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.50 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.459 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1184 _exptl_absorpt_coefficient_mu 0.787 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6944 _exptl_absorpt_correction_T_max 0.6944 _exptl_absorpt_process_details DENZO _exptl_special_details ; ? ; _diffrn_ambient_temperature 274(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'CCD scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 42261 _diffrn_reflns_av_R_equivalents 0.1206 _diffrn_reflns_av_sigmaI/netI 0.0553 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 27.48 _reflns_number_total 5934 _reflns_number_gt 4998 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'cOLLECT,Nonius BV, 1997-2001' _computing_cell_refinement DENZO/SCALEPACK _computing_data_reduction DENZO/SCALEPACK _computing_structure_solution SHELXs-97 _computing_structure_refinement SHELXL-97 _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^)+(0.0367P)^2^+1.5030P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5934 _refine_ls_number_parameters 311 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0482 _refine_ls_R_factor_gt 0.0353 _refine_ls_wR_factor_ref 0.0971 _refine_ls_wR_factor_gt 0.0903 _refine_ls_goodness_of_fit_ref 1.122 _refine_ls_restrained_S_all 1.122 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5793(3) 0.10172(14) 0.30427(18) 0.0252(5) Uani 1 1 d . . . C2 C 0.8382(3) 0.14756(16) 0.3597(2) 0.0367(7) Uani 1 1 d . . . H2A H 0.8841 0.1930 0.3533 0.044 Uiso 1 1 calc R . . H2B H 0.8677 0.1137 0.3197 0.044 Uiso 1 1 calc R . . C3 C 0.8944(3) 0.12204(16) 0.4562(2) 0.0425(8) Uani 1 1 d . . . H3A H 0.8904 0.1609 0.4973 0.051 Uiso 1 1 calc R . . H3B H 0.9968 0.1071 0.4667 0.051 Uiso 1 1 calc R . . C4 C 0.8017(3) 0.06008(17) 0.4750(2) 0.0425(8) Uani 1 1 d . . . H4A H 0.7126 0.0786 0.4882 0.051 Uiso 1 1 calc R . . H4B H 0.8574 0.0346 0.5280 0.051 Uiso 1 1 calc R . . C5 C 0.7582(3) 0.00842(16) 0.3960(2) 0.0362(7) Uani 1 1 d . . . H5A H 0.8435 0.0002 0.3722 0.043 Uiso 1 1 calc R . . H5B H 0.7309 -0.0368 0.4178 0.043 Uiso 1 1 calc R . . C6 C 0.6200(3) 0.22849(14) 0.3194(2) 0.0319(6) Uani 1 1 d . . . C7 C 0.6556(3) 0.27038(16) 0.2527(2) 0.0367(7) Uani 1 1 d . . . C8 C 0.6028(4) 0.34052(16) 0.2398(2) 0.0461(8) Uani 1 1 d . . . H8 H 0.6266 0.3692 0.1960 0.055 Uiso 1 1 calc R . . C9 C 0.5151(4) 0.36673(16) 0.2928(3) 0.0474(9) Uani 1 1 d . . . H9 H 0.4784 0.4130 0.2833 0.057 Uiso 1 1 calc R . . C10 C 0.4813(3) 0.32596(17) 0.3588(2) 0.0436(8) Uani 1 1 d . . . H10 H 0.4232 0.3447 0.3943 0.052 Uiso 1 1 calc R . . C11 C 0.5343(3) 0.25605(16) 0.3729(2) 0.0366(7) Uani 1 1 d . . . H11 H 0.5120 0.2282 0.4179 0.044 Uiso 1 1 calc R . . C12 C 0.7722(4) 0.28061(19) 0.1317(2) 0.0495(9) Uani 1 1 d . . . H12A H 0.6823 0.2967 0.0906 0.074 Uiso 1 1 calc R . . H12B H 0.8273 0.2521 0.0997 0.074 Uiso 1 1 calc R . . H12C H 0.8306 0.3210 0.1581 0.074 Uiso 1 1 calc R . . C13 C 0.5669(3) -0.02154(13) 0.25799(18) 0.0250(5) Uani 1 1 d . . . C14 C 0.6165(3) -0.02798(14) 0.17949(19) 0.0288(6) Uani 1 1 d . . . C15 C 0.5583(3) -0.08196(15) 0.1186(2) 0.0328(6) Uani 1 1 d . . . H15 H 0.5902 -0.0864 0.0661 0.039 Uiso 1 1 calc R . . C16 C 0.4537(3) -0.12944(14) 0.1342(2) 0.0308(6) Uani 1 1 d . . . C17 C 0.4086(3) -0.12238(14) 0.2132(2) 0.0299(6) Uani 1 1 d . . . H17 H 0.3387 -0.1541 0.2242 0.036 Uiso 1 1 calc R . . C18 C 0.4644(3) -0.06940(14) 0.27695(19) 0.0269(6) Uani 1 1 d . . . C19 C 0.7282(3) 0.02307(17) 0.1592(2) 0.0431(8) Uani 1 1 d . . . H19A H 0.7436 0.0122 0.1010 0.065 Uiso 1 1 calc R . . H19B H 0.8202 0.0186 0.2047 0.065 Uiso 1 1 calc R . . H19C H 0.6920 0.0710 0.1591 0.065 Uiso 1 1 calc R . . C20 C 0.3882(4) -0.18555(16) 0.0643(2) 0.0423(7) Uani 1 1 d . . . H20A H 0.3092 -0.1650 0.0183 0.063 Uiso 1 1 calc R . . H20B H 0.3502 -0.2242 0.0928 0.063 Uiso 1 1 calc R . . H20C H 0.4635 -0.2030 0.0374 0.063 Uiso 1 1 calc R . . C21 C 0.4133(3) -0.06579(16) 0.3623(2) 0.0356(7) Uani 1 1 d . . . H21A H 0.4838 -0.0897 0.4101 0.053 Uiso 1 1 calc R . . H21B H 0.3185 -0.0886 0.3527 0.053 Uiso 1 1 calc R . . H21C H 0.4051 -0.0168 0.3786 0.053 Uiso 1 1 calc R . . C22 C 0.3874(3) 0.16476(15) 0.13252(19) 0.0316(6) Uani 1 1 d . . . H22 H 0.4849 0.1745 0.1633 0.038 Uiso 1 1 calc R . . C23 C 0.3481(3) 0.09357(15) 0.11625(18) 0.0277(6) Uani 1 1 d . . . H23 H 0.4196 0.0593 0.1401 0.033 Uiso 1 1 calc R . . C24 C 0.1968(3) 0.06759(15) 0.06230(19) 0.0320(6) Uani 1 1 d . . . H24A H 0.1541 0.1029 0.0167 0.038 Uiso 1 1 calc R . . H24B H 0.2092 0.0238 0.0314 0.038 Uiso 1 1 calc R . . C25 C 0.0908(3) 0.05424(19) 0.1201(2) 0.0463(8) Uani 1 1 d . . . H25A H 0.0992 0.0048 0.1393 0.056 Uiso 1 1 calc R . . H25B H -0.0096 0.0618 0.0836 0.056 Uiso 1 1 calc R . . C26 C 0.1175(3) 0.10143(17) 0.2029(2) 0.0354(7) Uani 1 1 d . . . H26 H 0.1186 0.0793 0.2574 0.042 Uiso 1 1 calc R . . C27 C 0.1399(3) 0.17283(17) 0.2052(2) 0.0360(7) Uani 1 1 d . . . H27 H 0.1607 0.1959 0.2609 0.043 Uiso 1 1 calc R . . C28 C 0.1325(4) 0.21677(17) 0.1213(2) 0.0451(8) Uani 1 1 d . . . H28A H 0.0892 0.2628 0.1277 0.054 Uiso 1 1 calc R . . H28B H 0.0685 0.1930 0.0694 0.054 Uiso 1 1 calc R . . C29 C 0.2844(3) 0.22783(16) 0.1043(2) 0.0461(9) Uani 1 1 d . . . H29A H 0.2723 0.2368 0.0404 0.055 Uiso 1 1 calc R . . H29B H 0.3299 0.2697 0.1372 0.055 Uiso 1 1 calc R . . N1 N 0.6745(2) 0.15597(12) 0.33178(17) 0.0304(5) Uani 1 1 d . . . N2 N 0.6327(2) 0.03427(11) 0.32130(16) 0.0267(5) Uani 1 1 d . . . O1 O 0.7373(2) 0.23894(11) 0.20148(16) 0.0412(5) Uani 1 1 d . . . Cl1 Cl 0.32472(9) 0.11526(4) 0.40426(5) 0.03624(17) Uani 1 1 d . . . Rh1 Rh 0.356987(19) 0.119565(10) 0.252199(13) 0.02077(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0204(12) 0.0347(14) 0.0198(14) -0.0062(11) 0.0041(10) 0.0035(10) C2 0.0179(12) 0.0398(16) 0.048(2) -0.0133(14) 0.0003(12) 0.0006(11) C3 0.0269(14) 0.0469(18) 0.045(2) -0.0210(14) -0.0057(13) 0.0104(12) C4 0.0354(16) 0.0525(19) 0.0334(18) -0.0068(14) -0.0023(13) 0.0134(14) C5 0.0287(13) 0.0399(16) 0.0340(17) -0.0044(13) -0.0025(12) 0.0080(12) C6 0.0217(12) 0.0322(14) 0.0363(17) -0.0121(12) -0.0025(11) 0.0010(10) C7 0.0289(14) 0.0342(15) 0.044(2) -0.0147(13) 0.0029(13) -0.0049(11) C8 0.0448(17) 0.0315(16) 0.055(2) -0.0069(14) 0.0009(16) -0.0071(13) C9 0.0408(17) 0.0309(16) 0.063(3) -0.0196(16) -0.0013(17) 0.0022(13) C10 0.0290(14) 0.0452(18) 0.049(2) -0.0246(16) -0.0031(14) 0.0063(13) C11 0.0249(13) 0.0417(16) 0.0374(18) -0.0160(13) -0.0030(12) 0.0004(12) C12 0.0447(18) 0.055(2) 0.050(2) -0.0125(17) 0.0135(16) -0.0195(16) C13 0.0206(11) 0.0289(13) 0.0233(14) -0.0021(10) 0.0016(10) 0.0050(10) C14 0.0225(12) 0.0354(14) 0.0295(16) -0.0068(11) 0.0083(11) 0.0014(11) C15 0.0285(13) 0.0426(16) 0.0290(16) -0.0074(12) 0.0105(12) 0.0013(12) C16 0.0280(13) 0.0306(14) 0.0302(17) -0.0040(11) 0.0009(12) 0.0031(10) C17 0.0263(13) 0.0304(14) 0.0307(17) 0.0034(11) 0.0030(12) -0.0002(10) C18 0.0239(12) 0.0295(13) 0.0259(15) 0.0043(11) 0.0037(11) 0.0057(10) C19 0.0349(15) 0.0539(19) 0.048(2) -0.0194(15) 0.0235(15) -0.0113(14) C20 0.0491(18) 0.0401(16) 0.0346(19) -0.0085(13) 0.0053(15) -0.0052(14) C21 0.0409(16) 0.0356(15) 0.0319(17) 0.0015(12) 0.0124(13) 0.0003(12) C22 0.0238(12) 0.0452(16) 0.0243(15) 0.0055(12) 0.0038(11) -0.0109(11) C23 0.0240(12) 0.0422(15) 0.0174(14) 0.0019(11) 0.0066(11) 0.0032(11) C24 0.0314(14) 0.0351(15) 0.0276(16) -0.0040(12) 0.0042(12) -0.0045(11) C25 0.0400(17) 0.059(2) 0.042(2) -0.0093(16) 0.0129(15) -0.0230(15) C26 0.0176(12) 0.0580(19) 0.0309(17) -0.0024(14) 0.0069(11) -0.0079(12) C27 0.0232(13) 0.0526(19) 0.0293(17) -0.0016(13) 0.0016(11) 0.0128(12) C28 0.0479(18) 0.0378(17) 0.044(2) -0.0007(14) 0.0015(15) 0.0139(14) C29 0.0482(18) 0.0343(16) 0.045(2) 0.0166(14) -0.0086(15) -0.0132(13) N1 0.0176(10) 0.0316(12) 0.0377(14) -0.0084(10) -0.0004(9) 0.0015(9) N2 0.0208(10) 0.0311(12) 0.0258(13) -0.0045(9) 0.0020(9) 0.0051(9) O1 0.0384(11) 0.0380(11) 0.0494(14) -0.0101(10) 0.0154(10) -0.0065(9) Cl1 0.0411(4) 0.0448(4) 0.0253(4) 0.0023(3) 0.0130(3) 0.0085(3) Rh1 0.01718(11) 0.02517(12) 0.02015(13) -0.00046(7) 0.00517(8) 0.00127(7) _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 1.346(3) . ? C1 N2 1.360(3) . ? C1 Rh1 2.051(2) . ? C2 N1 1.487(3) . ? C2 C3 1.511(5) . ? C3 C4 1.521(5) . ? C4 C5 1.521(4) . ? C5 N2 1.492(3) . ? C6 C11 1.383(4) . ? C6 C7 1.395(4) . ? C6 N1 1.448(3) . ? C7 O1 1.362(3) . ? C7 C8 1.401(4) . ? C8 C9 1.383(5) . ? C9 C10 1.368(5) . ? C10 C11 1.398(4) . ? C12 O1 1.427(4) . ? C13 C18 1.396(4) . ? C13 C14 1.400(4) . ? C13 N2 1.451(3) . ? C14 C15 1.388(4) . ? C14 C19 1.506(4) . ? C15 C16 1.388(4) . ? C16 C17 1.385(4) . ? C16 C20 1.514(4) . ? C17 C18 1.396(4) . ? C18 C21 1.503(4) . ? C22 C23 1.390(4) . ? C22 C29 1.515(4) . ? C22 Rh1 2.103(3) . ? C23 C24 1.522(4) . ? C23 Rh1 2.118(3) . ? C24 C25 1.509(4) . ? C25 C26 1.513(4) . ? C26 C27 1.355(4) . ? C26 Rh1 2.196(3) . ? C27 C28 1.512(5) . ? C27 Rh1 2.208(3) . ? C28 C29 1.522(5) . ? Cl1 Rh1 2.4239(8) . ? 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 117.6(2) . . ? N1 C1 Rh1 121.30(18) . . ? N2 C1 Rh1 120.72(18) . . ? N1 C2 C3 112.8(3) . . ? C2 C3 C4 110.8(2) . . ? C3 C4 C5 112.6(3) . . ? N2 C5 C4 113.5(2) . . ? C11 C6 C7 120.4(3) . . ? C11 C6 N1 120.8(3) . . ? C7 C6 N1 118.8(3) . . ? O1 C7 C6 116.9(3) . . ? O1 C7 C8 123.7(3) . . ? C6 C7 C8 119.4(3) . . ? C9 C8 C7 119.4(3) . . ? C10 C9 C8 121.3(3) . . ? C9 C10 C11 119.9(3) . . ? C6 C11 C10 119.7(3) . . ? C18 C13 C14 121.3(2) . . ? C18 C13 N2 121.3(2) . . ? C14 C13 N2 117.3(2) . . ? C15 C14 C13 118.7(2) . . ? C15 C14 C19 119.9(3) . . ? C13 C14 C19 121.5(2) . . ? C16 C15 C14 121.6(3) . . ? C17 C16 C15 118.3(3) . . ? C17 C16 C20 121.7(3) . . ? C15 C16 C20 119.9(3) . . ? C16 C17 C18 122.4(3) . . ? C17 C18 C13 117.7(3) . . ? C17 C18 C21 119.7(2) . . ? C13 C18 C21 122.7(2) . . ? C23 C22 C29 125.5(2) . . ? C23 C22 Rh1 71.36(15) . . ? C29 C22 Rh1 110.2(2) . . ? C22 C23 C24 124.7(2) . . ? C22 C23 Rh1 70.19(16) . . ? C24 C23 Rh1 113.72(18) . . ? C25 C24 C23 113.2(2) . . ? C24 C25 C26 113.7(2) . . ? C27 C26 C25 126.3(3) . . ? C27 C26 Rh1 72.60(15) . . ? C25 C26 Rh1 108.18(19) . . ? C26 C27 C28 122.9(3) . . ? C26 C27 Rh1 71.58(16) . . ? C28 C27 Rh1 111.10(19) . . ? C27 C28 C29 112.3(2) . . ? C22 C29 C28 113.3(2) . . ? C1 N1 C6 119.2(2) . . ? C1 N1 C2 123.9(2) . . ? C6 N1 C2 116.0(2) . . ? C1 N2 C13 118.1(2) . . ? C1 N2 C5 128.8(2) . . ? C13 N2 C5 113.0(2) . . ? C7 O1 C12 117.6(3) . . ? C1 Rh1 C22 93.09(11) . . ? C1 Rh1 C23 97.09(10) . . ? C22 Rh1 C23 38.45(11) . . ? C1 Rh1 C26 161.49(12) . . ? C22 Rh1 C26 96.73(11) . . ? C23 Rh1 C26 81.27(11) . . ? C1 Rh1 C27 162.42(11) . . ? C22 Rh1 C27 81.52(11) . . ? C23 Rh1 C27 89.09(11) . . ? C26 Rh1 C27 35.82(11) . . ? C1 Rh1 Cl1 89.16(8) . . ? C22 Rh1 Cl1 158.10(8) . . ? C23 Rh1 Cl1 162.29(8) . . ? C26 Rh1 Cl1 87.54(9) . . ? C27 Rh1 Cl1 89.82(9) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.516 _refine_diff_density_min -1.248 _refine_diff_density_rms 0.248 # Attachment 'kjc0748.cif' data_kjc0748 _database_code_depnum_ccdc_archive 'CCDC 733093' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H33 N2 O, 0.75(B F4), I0.25' _chemical_formula_sum 'C24 H33 B0.75 F3 I0.25 N2 O' _chemical_formula_weight 462.36 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 0.0000 0.0000 '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' B B 0.0013 0.0007 '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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 15.1060(2) _cell_length_b 10.6720(2) _cell_length_c 15.6490(3) _cell_angle_alpha 90.00 _cell_angle_beta 108.8420(10) _cell_angle_gamma 90.00 _cell_volume 2387.60(7) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4332 _cell_measurement_theta_min 2.97 _cell_measurement_theta_max 27.51 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.286 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 972 _exptl_absorpt_coefficient_mu 0.412 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9221 _exptl_absorpt_correction_T_max 0.9221 _exptl_absorpt_process_details Denzo/Scalepack _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'CCD scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 36825 _diffrn_reflns_av_R_equivalents 0.1623 _diffrn_reflns_av_sigmaI/netI 0.0710 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 27.51 _reflns_number_total 5461 _reflns_number_gt 4332 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'cOLLECT,Nonius BV, 1997-2001' _computing_cell_refinement DENZO/SCALEPACK _computing_data_reduction DENZO/SCALEPACK _computing_structure_solution SHELXs-97 _computing_structure_refinement SHELXL-97 _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^)+(0.0261P)^2^+2.0320P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0164(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5461 _refine_ls_number_parameters 304 _refine_ls_number_restraints 214 _refine_ls_R_factor_all 0.0767 _refine_ls_R_factor_gt 0.0585 _refine_ls_wR_factor_ref 0.1467 _refine_ls_wR_factor_gt 0.1381 _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_restrained_S_all 1.089 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.33024(14) 0.06246(19) 0.56833(14) 0.0233(4) Uani 1 1 d U . . H1 H 0.3465 0.0649 0.5146 0.028 Uiso 1 1 calc R . . C2 C 0.37109(17) -0.0124(2) 0.72350(15) 0.0301(5) Uani 1 1 d U . . H2A H 0.4218 -0.0651 0.7630 0.036 Uiso 1 1 calc R . . H2B H 0.3130 -0.0629 0.7052 0.036 Uiso 1 1 calc R . . C3 C 0.35735(17) 0.1006(2) 0.77623(15) 0.0323(5) Uani 1 1 d U . . H3A H 0.4189 0.1394 0.8074 0.039 Uiso 1 1 calc R . . H3B H 0.3301 0.0732 0.8228 0.039 Uiso 1 1 calc R . . C4 C 0.29308(17) 0.1979(2) 0.71515(15) 0.0309(5) Uani 1 1 d U . . H4A H 0.2661 0.2515 0.7521 0.037 Uiso 1 1 calc R . . H4B H 0.3306 0.2522 0.6887 0.037 Uiso 1 1 calc R . . C5 C 0.21422(16) 0.1397(2) 0.63945(14) 0.0282(5) Uani 1 1 d U . . H5A H 0.1895 0.0663 0.6631 0.034 Uiso 1 1 calc R . . H5B H 0.1629 0.2014 0.6176 0.034 Uiso 1 1 calc R . . C6 C 0.49074(15) 0.0153(2) 0.64338(14) 0.0269(5) Uani 1 1 d U . . C7 C 0.53227(16) 0.1207(2) 0.61801(15) 0.0297(5) Uani 1 1 d U . . C8 C 0.62613(18) 0.1146(3) 0.62480(17) 0.0394(6) Uani 1 1 d U . . H8 H 0.6552 0.1841 0.6068 0.047 Uiso 1 1 calc R . . C9 C 0.67762(18) 0.0069(3) 0.65783(17) 0.0433(7) Uani 1 1 d U . . H9 H 0.7424 0.0048 0.6645 0.052 Uiso 1 1 calc R . . C10 C 0.63597(18) -0.0970(3) 0.68112(17) 0.0412(6) Uani 1 1 d U . . H10 H 0.6715 -0.1707 0.7024 0.049 Uiso 1 1 calc R . . C11 C 0.54152(17) -0.0930(2) 0.67321(15) 0.0336(5) Uani 1 1 d U . . H11 H 0.5121 -0.1645 0.6883 0.040 Uiso 1 1 calc R . . C12 C 0.5175(2) 0.3325(3) 0.5630(2) 0.0510(7) Uani 1 1 d U . . H12A H 0.5721 0.3595 0.6131 0.076 Uiso 1 1 calc R . . H12B H 0.4712 0.4002 0.5471 0.076 Uiso 1 1 calc R . . H12C H 0.5369 0.3119 0.5106 0.076 Uiso 1 1 calc R . . C13 C 0.17728(14) 0.1100(2) 0.47150(14) 0.0241(4) Uani 1 1 d U . . C14 C 0.13050(15) 0.0022(2) 0.42907(14) 0.0250(4) Uani 1 1 d U . . C15 C 0.06468(15) 0.0161(2) 0.34386(14) 0.0294(5) Uani 1 1 d U . . H15 H 0.0312 -0.0553 0.3138 0.035 Uiso 1 1 calc R . . C16 C 0.04704(17) 0.1323(2) 0.30188(15) 0.0332(5) Uani 1 1 d U . . H16 H 0.0013 0.1403 0.2439 0.040 Uiso 1 1 calc R . . C17 C 0.09621(17) 0.2363(2) 0.34461(16) 0.0339(5) Uani 1 1 d U . . H17 H 0.0853 0.3149 0.3144 0.041 Uiso 1 1 calc R . . C18 C 0.16118(16) 0.2286(2) 0.43071(15) 0.0288(5) Uani 1 1 d U . . C19 C 0.14972(16) -0.1274(2) 0.47230(15) 0.0294(5) Uani 1 1 d U . . H19 H 0.2150 -0.1277 0.5155 0.035 Uiso 1 1 calc R . . C20 C 0.0834(2) -0.1553(3) 0.5257(2) 0.0520(8) Uani 1 1 d U . . H20A H 0.0896 -0.0899 0.5712 0.078 Uiso 1 1 calc R . . H20B H 0.0991 -0.2368 0.5556 0.078 Uiso 1 1 calc R . . H20C H 0.0188 -0.1570 0.4845 0.078 Uiso 1 1 calc R . . C21 C 0.1425(2) -0.2309(2) 0.40299(18) 0.0412(6) Uani 1 1 d U . . H21A H 0.0765 -0.2458 0.3687 0.062 Uiso 1 1 calc R . . H21B H 0.1703 -0.3080 0.4341 0.062 Uiso 1 1 calc R . . H21C H 0.1758 -0.2052 0.3616 0.062 Uiso 1 1 calc R . . C22 C 0.20960(18) 0.3473(2) 0.47710(16) 0.0335(5) Uani 1 1 d U . . H22 H 0.2561 0.3229 0.5364 0.040 Uiso 1 1 calc R . . C23 C 0.1380(2) 0.4353(2) 0.49576(19) 0.0455(6) Uani 1 1 d U . . H23A H 0.1702 0.5087 0.5293 0.068 Uiso 1 1 calc R . . H23B H 0.1052 0.3912 0.5315 0.068 Uiso 1 1 calc R . . H23C H 0.0927 0.4625 0.4384 0.068 Uiso 1 1 calc R . . C24 C 0.2624(2) 0.4135(3) 0.42115(19) 0.0459(7) Uani 1 1 d U . . H24A H 0.3098 0.3568 0.4123 0.069 Uiso 1 1 calc R . . H24B H 0.2930 0.4889 0.4531 0.069 Uiso 1 1 calc R . . H24C H 0.2183 0.4373 0.3623 0.069 Uiso 1 1 calc R . . N1 N 0.39497(12) 0.02302(16) 0.64168(11) 0.0246(4) Uani 1 1 d U . . N2 N 0.24526(12) 0.09886(16) 0.56182(11) 0.0237(4) Uani 1 1 d U . . O1 O 0.47658(12) 0.22268(15) 0.59001(12) 0.0369(4) Uani 1 1 d U . . F1 F 0.3074(2) -0.3080(2) 0.59415(18) 0.0838(9) Uani 0.75 1 d PDU . . F2 F 0.33712(16) -0.48836(18) 0.67651(16) 0.0563(6) Uani 0.75 1 d PDU . . F3 F 0.45146(18) -0.3999(2) 0.63137(16) 0.0613(7) Uani 0.75 1 d PDU . . F4 F 0.40464(13) -0.30568(17) 0.73840(12) 0.0384(4) Uani 0.75 1 d PDU . . I1 I 0.36387(8) -0.36333(12) 0.63997(6) 0.0370(3) Uani 0.25 1 d PU . . B1 B 0.3731(6) -0.3741(7) 0.6594(5) 0.0385(7) Uani 0.75 1 d PDU . . 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 0.0286(11) 0.0222(10) 0.0193(10) -0.0020(8) 0.0081(8) -0.0031(8) C2 0.0352(12) 0.0327(12) 0.0239(11) 0.0084(9) 0.0116(9) 0.0006(10) C3 0.0319(12) 0.0429(14) 0.0220(11) -0.0008(10) 0.0085(9) -0.0026(10) C4 0.0362(12) 0.0312(12) 0.0258(11) -0.0055(9) 0.0107(10) -0.0004(10) C5 0.0304(11) 0.0355(12) 0.0203(11) -0.0002(9) 0.0102(9) 0.0040(9) C6 0.0258(11) 0.0341(12) 0.0205(10) -0.0051(9) 0.0072(8) 0.0000(9) C7 0.0329(12) 0.0355(12) 0.0223(11) -0.0055(9) 0.0112(9) -0.0026(9) C8 0.0371(13) 0.0544(16) 0.0309(13) -0.0060(11) 0.0167(11) -0.0082(12) C9 0.0316(13) 0.0712(19) 0.0298(13) -0.0085(12) 0.0136(11) 0.0005(13) C10 0.0360(13) 0.0542(16) 0.0327(13) -0.0023(12) 0.0101(11) 0.0147(12) C11 0.0335(12) 0.0374(13) 0.0280(12) 0.0004(10) 0.0074(10) 0.0049(10) C12 0.0647(19) 0.0412(15) 0.0554(18) 0.0073(13) 0.0309(16) -0.0110(14) C13 0.0243(10) 0.0282(11) 0.0191(10) 0.0007(8) 0.0060(8) 0.0009(8) C14 0.0259(10) 0.0261(11) 0.0229(10) -0.0001(8) 0.0080(8) 0.0009(8) C15 0.0285(11) 0.0322(12) 0.0247(11) -0.0039(9) 0.0047(9) 0.0000(9) C16 0.0354(12) 0.0385(13) 0.0220(11) 0.0018(9) 0.0043(10) 0.0033(10) C17 0.0422(13) 0.0304(12) 0.0275(12) 0.0068(9) 0.0089(10) 0.0050(10) C18 0.0343(12) 0.0269(11) 0.0251(11) 0.0007(9) 0.0095(9) 0.0004(9) C19 0.0312(12) 0.0243(11) 0.0289(12) 0.0007(9) 0.0044(9) -0.0003(9) C20 0.074(2) 0.0375(15) 0.0558(18) 0.0118(13) 0.0373(17) 0.0000(14) C21 0.0508(15) 0.0260(12) 0.0438(15) -0.0046(10) 0.0108(12) -0.0007(11) C22 0.0445(14) 0.0251(11) 0.0287(12) 0.0028(9) 0.0087(10) -0.0028(10) C23 0.0596(17) 0.0307(13) 0.0453(16) -0.0050(11) 0.0154(13) -0.0007(12) C24 0.0597(17) 0.0362(14) 0.0440(16) 0.0029(12) 0.0196(14) -0.0127(13) N1 0.0266(9) 0.0262(9) 0.0209(9) 0.0000(7) 0.0076(7) -0.0003(7) N2 0.0281(9) 0.0239(9) 0.0188(9) -0.0002(7) 0.0071(7) -0.0017(7) O1 0.0441(10) 0.0289(9) 0.0422(10) 0.0018(7) 0.0202(8) -0.0048(7) F1 0.089(2) 0.0546(15) 0.0649(17) 0.0141(13) -0.0346(15) 0.0250(14) F2 0.0544(14) 0.0335(11) 0.0757(16) -0.0016(10) 0.0136(12) -0.0078(10) F3 0.0834(17) 0.0606(14) 0.0581(15) 0.0000(11) 0.0481(14) 0.0100(13) F4 0.0421(11) 0.0334(10) 0.0407(11) -0.0030(8) 0.0147(9) 0.0004(8) I1 0.0356(4) 0.0415(4) 0.0334(6) -0.0029(4) 0.0105(4) 0.0002(3) B1 0.0363(10) 0.0414(10) 0.0355(12) -0.0022(10) 0.0083(10) 0.0011(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N2 1.313(3) . ? C1 N1 1.314(3) . ? C1 H1 0.9500 . ? C2 N1 1.487(3) . ? C2 C3 1.513(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.528(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.515(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 N2 1.501(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C11 1.383(3) . ? C6 C7 1.406(3) . ? C6 N1 1.441(3) . ? C7 O1 1.359(3) . ? C7 C8 1.389(3) . ? C8 C9 1.390(4) . ? C8 H8 0.9500 . ? C9 C10 1.381(4) . ? C9 H9 0.9500 . ? C10 C11 1.392(3) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 O1 1.450(3) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.400(3) . ? C13 C18 1.403(3) . ? C13 N2 1.459(3) . ? C14 C15 1.390(3) . ? C14 C19 1.526(3) . ? C15 C16 1.388(3) . ? C15 H15 0.9500 . ? C16 C17 1.383(3) . ? C16 H16 0.9500 . ? C17 C18 1.390(3) . ? C17 H17 0.9500 . ? C18 C22 1.525(3) . ? C19 C21 1.526(3) . ? C19 C20 1.527(3) . ? C19 H19 1.0000 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 C23 1.530(4) . ? C22 C24 1.534(3) . ? C22 H22 1.0000 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? F1 I1 1.094(3) . ? F1 B1 1.368(7) . ? F2 B1 1.396(8) . ? F2 I1 1.556(2) . ? F3 B1 1.416(8) . ? F3 I1 1.427(3) . ? F4 B1 1.382(8) . ? F4 I1 1.587(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C1 N1 126.56(19) . . ? N2 C1 H1 116.7 . . ? N1 C1 H1 116.7 . . ? N1 C2 C3 112.41(18) . . ? N1 C2 H2A 109.1 . . ? C3 C2 H2A 109.1 . . ? N1 C2 H2B 109.1 . . ? C3 C2 H2B 109.1 . . ? H2A C2 H2B 107.9 . . ? C2 C3 C4 111.83(18) . . ? C2 C3 H3A 109.3 . . ? C4 C3 H3A 109.3 . . ? C2 C3 H3B 109.3 . . ? C4 C3 H3B 109.3 . . ? H3A C3 H3B 107.9 . . ? C5 C4 C3 113.00(19) . . ? C5 C4 H4A 109.0 . . ? C3 C4 H4A 109.0 . . ? C5 C4 H4B 109.0 . . ? C3 C4 H4B 109.0 . . ? H4A C4 H4B 107.8 . . ? N2 C5 C4 112.30(18) . . ? N2 C5 H5A 109.1 . . ? C4 C5 H5A 109.1 . . ? N2 C5 H5B 109.1 . . ? C4 C5 H5B 109.1 . . ? H5A C5 H5B 107.9 . . ? C11 C6 C7 121.0(2) . . ? C11 C6 N1 119.9(2) . . ? C7 C6 N1 119.09(19) . . ? O1 C7 C8 124.9(2) . . ? O1 C7 C6 116.46(19) . . ? C8 C7 C6 118.6(2) . . ? C7 C8 C9 120.1(2) . . ? C7 C8 H8 119.9 . . ? C9 C8 H8 119.9 . . ? C10 C9 C8 120.9(2) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C9 C10 C11 119.6(2) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C6 C11 C10 119.8(2) . . ? C6 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? O1 C12 H12A 109.5 . . ? O1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C18 122.6(2) . . ? C14 C13 N2 118.84(18) . . ? C18 C13 N2 118.57(18) . . ? C15 C14 C13 117.57(19) . . ? C15 C14 C19 119.76(19) . . ? C13 C14 C19 122.67(19) . . ? C16 C15 C14 121.2(2) . . ? C16 C15 H15 119.4 . . ? C14 C15 H15 119.4 . . ? C17 C16 C15 119.8(2) . . ? C17 C16 H16 120.1 . . ? C15 C16 H16 120.1 . . ? C16 C17 C18 121.5(2) . . ? C16 C17 H17 119.3 . . ? C18 C17 H17 119.3 . . ? C17 C18 C13 117.3(2) . . ? C17 C18 C22 119.5(2) . . ? C13 C18 C22 123.2(2) . . ? C14 C19 C21 112.39(19) . . ? C14 C19 C20 110.77(19) . . ? C21 C19 C20 109.8(2) . . ? C14 C19 H19 107.9 . . ? C21 C19 H19 107.9 . . ? C20 C19 H19 107.9 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C18 C22 C23 109.9(2) . . ? C18 C22 C24 111.7(2) . . ? C23 C22 C24 110.9(2) . . ? C18 C22 H22 108.1 . . ? C23 C22 H22 108.1 . . ? C24 C22 H22 108.1 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C1 N1 C6 119.60(17) . . ? C1 N1 C2 120.98(18) . . ? C6 N1 C2 119.41(17) . . ? C1 N2 C13 117.63(16) . . ? C1 N2 C5 125.18(18) . . ? C13 N2 C5 117.01(16) . . ? C7 O1 C12 117.6(2) . . ? I1 F1 B1 7.0(4) . . ? B1 F2 I1 10.4(3) . . ? B1 F3 I1 12.6(3) . . ? B1 F4 I1 9.1(3) . . ? F1 I1 F3 129.6(2) . . ? F1 I1 F2 117.6(2) . . ? F3 I1 F2 99.14(14) . . ? F1 I1 F4 113.78(19) . . ? F3 I1 F4 96.70(14) . . ? F2 I1 F4 92.37(12) . . ? F1 B1 F4 110.6(6) . . ? F1 B1 F2 111.1(6) . . ? F4 B1 F2 109.4(5) . . ? F1 B1 F3 110.3(5) . . ? F4 B1 F3 107.4(5) . . ? F2 B1 F3 107.8(6) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.374 _refine_diff_density_min -0.451 _refine_diff_density_rms 0.054 # Attachment 'kjc0757.cif' data_kjc0757_2 _database_code_depnum_ccdc_archive 'CCDC 733094' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H36 Cl N2 O Rh, C1 H2 Cl2' _chemical_formula_sum 'C29 H38 Cl3 N2 O Rh' _chemical_formula_weight 639.87 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 0.0000 0.0000 '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 0.0060 '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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.7164(2) _cell_length_b 11.4614(4) _cell_length_c 13.2888(4) _cell_angle_alpha 86.629(2) _cell_angle_beta 78.935(2) _cell_angle_gamma 82.3150(10) _cell_volume 1438.50(7) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5502 _cell_measurement_theta_min 2.97 _cell_measurement_theta_max 27.49 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.477 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 660 _exptl_absorpt_coefficient_mu 0.897 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8410 _exptl_absorpt_correction_T_max 0.9156 _exptl_absorpt_process_details Denzo/Scalepack _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'CCD scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22407 _diffrn_reflns_av_R_equivalents 0.1097 _diffrn_reflns_av_sigmaI/netI 0.0768 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 27.49 _reflns_number_total 6485 _reflns_number_gt 5502 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'cOLLECT,Nonius BV, 1997-2001' _computing_cell_refinement DENZO/SCALEPACK _computing_data_reduction DENZO/SCALEPACK _computing_structure_solution SHELXs-97 _computing_structure_refinement SHELXL-97 _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^)+(0.0387P)^2^+1.1083P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6485 _refine_ls_number_parameters 329 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0539 _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_ref 0.1048 _refine_ls_wR_factor_gt 0.0982 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Rh1 Rh 0.85814(2) 0.304045(19) 0.257020(16) 0.01907(8) Uani 1 1 d . . . Cl2 Cl 0.94483(8) 0.17670(6) 0.11507(6) 0.02730(17) Uani 1 1 d . . . C3 C 0.6624(3) 0.2965(2) 0.2215(2) 0.0188(6) Uani 1 1 d . . . N4 N 0.6077(3) 0.3659(2) 0.14988(19) 0.0218(5) Uani 1 1 d . . . C5 C 0.4959(4) 0.3367(3) 0.0976(3) 0.0314(8) Uani 1 1 d . . . H5A H 0.5186 0.3591 0.0238 0.038 Uiso 1 1 calc R . . H5B H 0.4043 0.3818 0.1272 0.038 Uiso 1 1 calc R . . C6 C 0.4842(4) 0.2059(3) 0.1101(3) 0.0336(8) Uani 1 1 d . . . H6A H 0.3989 0.1889 0.0861 0.040 Uiso 1 1 calc R . . H6B H 0.5679 0.1612 0.0684 0.040 Uiso 1 1 calc R . . C7 C 0.4750(3) 0.1689(3) 0.2215(3) 0.0305(7) Uani 1 1 d . . . H7A H 0.3876 0.2092 0.2627 0.037 Uiso 1 1 calc R . . H7B H 0.4722 0.0828 0.2303 0.037 Uiso 1 1 calc R . . N8 N 0.5998(3) 0.2007(2) 0.25612(18) 0.0224(5) Uani 1 1 d . . . C9 C 0.6409(3) 0.1354(2) 0.3441(2) 0.0221(6) Uani 1 1 d . . . C10 C 0.5622(3) 0.1636(3) 0.4405(2) 0.0269(7) Uani 1 1 d . . . O11 O 0.4522(2) 0.2515(2) 0.44064(18) 0.0338(5) Uani 1 1 d . . . C12 C 0.3762(4) 0.2940(4) 0.5372(3) 0.0447(9) Uani 1 1 d . . . H12A H 0.3308 0.2302 0.5769 0.067 Uiso 1 1 calc R . . H12B H 0.3039 0.3590 0.5257 0.067 Uiso 1 1 calc R . . H12C H 0.4417 0.3220 0.5752 0.067 Uiso 1 1 calc R . . C13 C 0.5998(4) 0.1052(3) 0.5285(3) 0.0338(8) Uani 1 1 d . . . H13 H 0.5473 0.1246 0.5946 0.041 Uiso 1 1 calc R . . C14 C 0.7151(4) 0.0184(3) 0.5174(3) 0.0389(9) Uani 1 1 d . . . H14 H 0.7425 -0.0210 0.5768 0.047 Uiso 1 1 calc R . . C15 C 0.7908(4) -0.0117(3) 0.4219(3) 0.0370(8) Uani 1 1 d . . . H15 H 0.8683 -0.0725 0.4155 0.044 Uiso 1 1 calc R . . C16 C 0.7532(3) 0.0475(3) 0.3345(3) 0.0287(7) Uani 1 1 d . . . H16 H 0.8052 0.0272 0.2685 0.034 Uiso 1 1 calc R . . C17 C 0.6367(3) 0.4874(3) 0.1349(2) 0.0223(6) Uani 1 1 d . . . C18 C 0.7417(3) 0.5208(3) 0.0553(2) 0.0238(6) Uani 1 1 d . . . C19 C 0.7674(3) 0.6387(3) 0.0478(2) 0.0257(7) Uani 1 1 d . . . H19 H 0.8416 0.6622 -0.0037 0.031 Uiso 1 1 calc R . . C20 C 0.6870(3) 0.7220(3) 0.1141(2) 0.0274(7) Uani 1 1 d . . . C21 C 0.5784(3) 0.6869(3) 0.1880(2) 0.0272(7) Uani 1 1 d . . . H21 H 0.5203 0.7442 0.2314 0.033 Uiso 1 1 calc R . . C22 C 0.5513(3) 0.5693(3) 0.2008(2) 0.0248(6) Uani 1 1 d . . . C23 C 0.4393(3) 0.5344(3) 0.2875(3) 0.0335(8) Uani 1 1 d . . . H23A H 0.3876 0.4767 0.2639 0.050 Uiso 1 1 calc R . . H23B H 0.3736 0.6042 0.3107 0.050 Uiso 1 1 calc R . . H23C H 0.4836 0.4994 0.3444 0.050 Uiso 1 1 calc R . . C24 C 0.7175(4) 0.8492(3) 0.1052(3) 0.0390(9) Uani 1 1 d . . . H24A H 0.6346 0.9006 0.0898 0.059 Uiso 1 1 calc R . . H24B H 0.7986 0.8576 0.0499 0.059 Uiso 1 1 calc R . . H24C H 0.7389 0.8713 0.1701 0.059 Uiso 1 1 calc R . . C25 C 0.8236(4) 0.4351(3) -0.0213(3) 0.0334(7) Uani 1 1 d . . . H25A H 0.7613 0.4131 -0.0650 0.050 Uiso 1 1 calc R . . H25B H 0.8615 0.3646 0.0147 0.050 Uiso 1 1 calc R . . H25C H 0.9017 0.4714 -0.0637 0.050 Uiso 1 1 calc R . . C26 C 0.8075(3) 0.4650(3) 0.3324(2) 0.0226(6) Uani 1 1 d . . . H26 H 0.7353 0.4851 0.2931 0.027 Uiso 1 1 calc R . . C27 C 0.7889(3) 0.3737(3) 0.4056(2) 0.0243(6) Uani 1 1 d . . . H27 H 0.7075 0.3346 0.4107 0.029 Uiso 1 1 calc R . . C28 C 0.8913(4) 0.3327(3) 0.4782(3) 0.0359(8) Uani 1 1 d . . . H28A H 0.9358 0.4009 0.4933 0.043 Uiso 1 1 calc R . . H28B H 0.8374 0.3037 0.5437 0.043 Uiso 1 1 calc R . . C29 C 1.0067(4) 0.2359(3) 0.4356(3) 0.0378(8) Uani 1 1 d . . . H29A H 1.0916 0.2418 0.4650 0.045 Uiso 1 1 calc R . . H29B H 0.9744 0.1586 0.4581 0.045 Uiso 1 1 calc R . . C30 C 1.0475(3) 0.2403(3) 0.3196(3) 0.0330(8) Uani 1 1 d . . . H30 H 1.0545 0.1687 0.2854 0.040 Uiso 1 1 calc R . . C31 C 1.0754(3) 0.3399(3) 0.2600(3) 0.0289(7) Uani 1 1 d . . . H31 H 1.0966 0.3330 0.1876 0.035 Uiso 1 1 calc R . . C32 C 1.0743(3) 0.4596(3) 0.3029(3) 0.0319(7) Uani 1 1 d . . . H32A H 1.1477 0.5014 0.2586 0.038 Uiso 1 1 calc R . . H32B H 1.0984 0.4489 0.3722 0.038 Uiso 1 1 calc R . . C33 C 0.9313(3) 0.5351(3) 0.3096(3) 0.0285(7) Uani 1 1 d . . . H33A H 0.9210 0.5928 0.3640 0.034 Uiso 1 1 calc R . . H33B H 0.9292 0.5798 0.2438 0.034 Uiso 1 1 calc R . . Cl34 Cl 1.07571(15) 0.79781(11) 0.23117(10) 0.0739(4) Uani 1 1 d . . . C35 C 1.1394(4) 0.8947(3) 0.1318(3) 0.0396(9) Uani 1 1 d . . . H35A H 1.0684 0.9650 0.1302 0.047 Uiso 1 1 calc R . . H35B H 1.1528 0.8557 0.0655 0.047 Uiso 1 1 calc R . . Cl36 Cl 1.29977(12) 0.93924(11) 0.14632(10) 0.0659(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Rh1 0.01784(13) 0.01857(13) 0.02191(13) -0.00231(9) -0.00814(9) 0.00083(9) Cl2 0.0304(4) 0.0238(4) 0.0263(4) -0.0048(3) -0.0058(3) 0.0041(3) C3 0.0175(14) 0.0185(14) 0.0216(14) -0.0056(11) -0.0071(11) 0.0006(11) N4 0.0216(13) 0.0193(12) 0.0277(13) 0.0016(10) -0.0137(11) -0.0017(10) C5 0.0352(18) 0.0287(17) 0.0380(18) 0.0057(14) -0.0253(15) -0.0082(14) C6 0.0395(19) 0.0315(18) 0.0383(19) 0.0028(15) -0.0237(16) -0.0127(15) C7 0.0316(18) 0.0269(17) 0.0396(18) 0.0025(14) -0.0174(15) -0.0129(14) N8 0.0249(13) 0.0211(13) 0.0243(13) 0.0004(10) -0.0109(10) -0.0050(10) C9 0.0243(15) 0.0168(14) 0.0277(15) 0.0024(12) -0.0089(12) -0.0065(12) C10 0.0290(17) 0.0231(16) 0.0315(17) -0.0001(13) -0.0093(14) -0.0089(13) O11 0.0343(13) 0.0313(13) 0.0336(13) -0.0064(10) -0.0036(10) 0.0021(10) C12 0.047(2) 0.043(2) 0.040(2) -0.0175(17) 0.0014(17) -0.0001(18) C13 0.044(2) 0.0336(19) 0.0263(17) 0.0003(14) -0.0071(15) -0.0118(16) C14 0.048(2) 0.035(2) 0.037(2) 0.0126(16) -0.0190(17) -0.0076(17) C15 0.038(2) 0.0296(18) 0.045(2) 0.0091(16) -0.0175(17) -0.0009(15) C16 0.0322(18) 0.0226(16) 0.0316(17) 0.0021(13) -0.0070(14) -0.0039(13) C17 0.0216(15) 0.0220(15) 0.0264(15) 0.0023(12) -0.0131(12) -0.0024(12) C18 0.0249(15) 0.0228(15) 0.0253(15) 0.0003(12) -0.0120(12) 0.0016(12) C19 0.0287(16) 0.0228(16) 0.0263(16) 0.0046(12) -0.0089(13) -0.0025(13) C20 0.0336(18) 0.0208(15) 0.0311(17) 0.0028(13) -0.0162(14) -0.0023(13) C21 0.0279(16) 0.0219(16) 0.0326(17) -0.0032(13) -0.0120(13) 0.0040(13) C22 0.0214(15) 0.0266(16) 0.0285(16) 0.0008(13) -0.0127(13) 0.0007(12) C23 0.0253(17) 0.0366(19) 0.0379(19) -0.0028(15) -0.0035(14) -0.0035(14) C24 0.051(2) 0.0254(18) 0.044(2) -0.0020(15) -0.0136(18) -0.0097(16) C25 0.039(2) 0.0272(17) 0.0316(18) 0.0003(14) -0.0056(15) 0.0027(15) C26 0.0207(14) 0.0220(15) 0.0284(16) -0.0087(12) -0.0108(12) -0.0020(12) C27 0.0253(16) 0.0272(16) 0.0231(15) -0.0086(12) -0.0068(12) -0.0063(13) C28 0.046(2) 0.036(2) 0.0300(18) -0.0016(15) -0.0185(16) -0.0047(16) C29 0.044(2) 0.0358(19) 0.041(2) 0.0034(16) -0.0285(17) -0.0016(16) C30 0.0249(16) 0.0353(19) 0.044(2) -0.0071(15) -0.0232(15) 0.0059(14) C31 0.0138(14) 0.0374(18) 0.0376(18) -0.0095(15) -0.0102(13) 0.0005(13) C32 0.0231(16) 0.0394(19) 0.0356(18) -0.0051(15) -0.0081(14) -0.0069(14) C33 0.0309(17) 0.0251(16) 0.0337(17) -0.0022(13) -0.0123(14) -0.0087(14) Cl34 0.0850(9) 0.0458(7) 0.0811(9) 0.0091(6) 0.0128(7) -0.0186(6) C35 0.043(2) 0.0286(18) 0.051(2) -0.0017(16) -0.0147(18) -0.0061(16) Cl36 0.0514(7) 0.0624(7) 0.0929(9) 0.0064(6) -0.0294(6) -0.0203(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Rh1 C3 2.059(3) . ? Rh1 C26 2.106(3) . ? Rh1 C27 2.126(3) . ? Rh1 C30 2.184(3) . ? Rh1 C31 2.212(3) . ? Rh1 Cl2 2.4049(8) . ? C3 N8 1.341(3) . ? C3 N4 1.347(4) . ? N4 C17 1.452(4) . ? N4 C5 1.479(3) . ? C5 C6 1.515(4) . ? C6 C7 1.504(4) . ? C7 N8 1.472(3) . ? N8 C9 1.443(4) . ? C9 C16 1.375(5) . ? C9 C10 1.392(4) . ? C10 O11 1.367(4) . ? C10 C13 1.399(4) . ? O11 C12 1.429(4) . ? C13 C14 1.387(5) . ? C14 C15 1.377(5) . ? C15 C16 1.395(4) . ? C17 C22 1.395(4) . ? C17 C18 1.396(4) . ? C18 C19 1.401(4) . ? C18 C25 1.494(5) . ? C19 C20 1.391(5) . ? C20 C21 1.381(4) . ? C20 C24 1.520(4) . ? C21 C22 1.403(4) . ? C22 C23 1.500(4) . ? C26 C27 1.391(4) . ? C26 C33 1.508(4) . ? C27 C28 1.528(4) . ? C28 C29 1.518(5) . ? C29 C30 1.515(5) . ? C30 C31 1.378(5) . ? C31 C32 1.515(5) . ? C32 C33 1.525(5) . ? Cl34 C35 1.748(4) . ? C35 Cl36 1.751(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 Rh1 C26 97.11(11) . . ? C3 Rh1 C27 97.97(11) . . ? C26 Rh1 C27 38.37(11) . . ? C3 Rh1 C30 156.33(12) . . ? C26 Rh1 C30 97.44(12) . . ? C27 Rh1 C30 82.24(13) . . ? C3 Rh1 C31 165.78(12) . . ? C26 Rh1 C31 81.58(12) . . ? C27 Rh1 C31 89.78(12) . . ? C30 Rh1 C31 36.53(12) . . ? C3 Rh1 Cl2 84.94(8) . . ? C26 Rh1 Cl2 156.50(9) . . ? C27 Rh1 Cl2 164.66(9) . . ? C30 Rh1 Cl2 89.09(10) . . ? C31 Rh1 Cl2 90.73(9) . . ? N8 C3 N4 117.2(2) . . ? N8 C3 Rh1 116.60(19) . . ? N4 C3 Rh1 124.58(19) . . ? C3 N4 C17 119.4(2) . . ? C3 N4 C5 124.8(2) . . ? C17 N4 C5 114.7(2) . . ? N4 C5 C6 110.1(2) . . ? C7 C6 C5 109.1(3) . . ? N8 C7 C6 108.5(2) . . ? C3 N8 C9 118.4(2) . . ? C3 N8 C7 123.9(2) . . ? C9 N8 C7 116.9(2) . . ? C16 C9 C10 120.2(3) . . ? C16 C9 N8 121.9(3) . . ? C10 C9 N8 117.8(3) . . ? O11 C10 C9 115.1(3) . . ? O11 C10 C13 124.7(3) . . ? C9 C10 C13 120.1(3) . . ? C10 O11 C12 118.3(3) . . ? C14 C13 C10 118.8(3) . . ? C15 C14 C13 121.1(3) . . ? C14 C15 C16 119.8(3) . . ? C9 C16 C15 119.9(3) . . ? C22 C17 C18 121.8(3) . . ? C22 C17 N4 117.0(3) . . ? C18 C17 N4 121.1(3) . . ? C17 C18 C19 118.0(3) . . ? C17 C18 C25 121.7(3) . . ? C19 C18 C25 120.3(3) . . ? C20 C19 C18 121.5(3) . . ? C21 C20 C19 118.7(3) . . ? C21 C20 C24 120.7(3) . . ? C19 C20 C24 120.7(3) . . ? C20 C21 C22 122.0(3) . . ? C17 C22 C21 117.8(3) . . ? C17 C22 C23 122.4(3) . . ? C21 C22 C23 119.7(3) . . ? C27 C26 C33 126.2(3) . . ? C27 C26 Rh1 71.61(17) . . ? C33 C26 Rh1 110.3(2) . . ? C26 C27 C28 124.0(3) . . ? C26 C27 Rh1 70.02(17) . . ? C28 C27 Rh1 112.7(2) . . ? C29 C28 C27 113.5(3) . . ? C30 C29 C28 114.0(3) . . ? C31 C30 C29 125.1(3) . . ? C31 C30 Rh1 72.83(17) . . ? C29 C30 Rh1 108.1(2) . . ? C30 C31 C32 123.9(3) . . ? C30 C31 Rh1 70.64(17) . . ? C32 C31 Rh1 111.0(2) . . ? C31 C32 C33 112.4(2) . . ? C26 C33 C32 113.7(3) . . ? Cl34 C35 Cl36 112.1(2) . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.605 _refine_diff_density_min -0.920 _refine_diff_density_rms 0.108 # Attachment 'kjc0801.cif' data_kjc0801 _database_code_depnum_ccdc_archive 'CCDC 733095' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H32 Cl N2 O2 Rh, 0.5(C6 H14)' _chemical_formula_sum 'C29 H39 Cl N2 O2 Rh' _chemical_formula_weight 585.98 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 0.0000 0.0000 '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 0.0060 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.7607(2) _cell_length_b 18.7624(3) _cell_length_c 14.8596(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.0190(10) _cell_angle_gamma 90.00 _cell_volume 2694.69(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4619 _cell_measurement_theta_min 2.97 _cell_measurement_theta_max 27.42 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.444 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1220 _exptl_absorpt_coefficient_mu 0.762 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7504 _exptl_absorpt_correction_T_max 0.9277 _exptl_absorpt_process_details Denzo _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'CCD scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 44792 _diffrn_reflns_av_R_equivalents 0.1671 _diffrn_reflns_av_sigmaI/netI 0.0793 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 27.42 _reflns_number_total 6122 _reflns_number_gt 4619 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'cOLLECT,Nonius BV, 1997-2001' _computing_cell_refinement DENZO/SCALEPACK _computing_data_reduction DENZO/SCALEPACK _computing_structure_solution SHELXs-97 _computing_structure_refinement SHELXL-97 _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^)+(0.0512P)^2^+10.0137P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6122 _refine_ls_number_parameters 318 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0892 _refine_ls_R_factor_gt 0.0610 _refine_ls_wR_factor_ref 0.1535 _refine_ls_wR_factor_gt 0.1392 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.055 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3175(5) 0.2061(3) 0.3023(4) 0.0288(11) Uani 1 1 d . . . C2 C 0.0705(6) 0.2261(3) 0.2359(6) 0.061(2) Uani 1 1 d . . . H2A H 0.0576 0.2142 0.1717 0.073 Uiso 1 1 calc R . . H2B H -0.0142 0.2147 0.2600 0.073 Uiso 1 1 calc R . . C3 C 0.1002(6) 0.3018(3) 0.2474(5) 0.0535(17) Uani 1 1 d . . . H3A H 0.0891 0.3152 0.3090 0.064 Uiso 1 1 calc R . . H3B H 0.0324 0.3282 0.2065 0.064 Uiso 1 1 calc R . . C4 C 0.2381(6) 0.3228(3) 0.2305(5) 0.058(2) Uani 1 1 d . . . H4A H 0.2580 0.3706 0.2536 0.070 Uiso 1 1 calc R . . H4B H 0.2414 0.3233 0.1656 0.070 Uiso 1 1 calc R . . C5 C 0.1493(5) 0.1143(3) 0.3128(4) 0.0287(11) Uani 1 1 d . . . C6 C 0.0863(6) 0.0665(3) 0.2475(4) 0.0412(13) Uani 1 1 d . . . C7 C 0.0445(6) -0.0011(3) 0.2753(5) 0.0506(17) Uani 1 1 d . . . H7 H 0.0023 -0.0332 0.2325 0.061 Uiso 1 1 calc R . . C8 C 0.0662(6) -0.0190(3) 0.3646(5) 0.0437(14) Uani 1 1 d . . . H8 H 0.0374 -0.0633 0.3829 0.052 Uiso 1 1 calc R . . C9 C 0.1295(5) 0.0271(3) 0.4279(4) 0.0383(13) Uani 1 1 d . . . H9 H 0.1449 0.0138 0.4888 0.046 Uiso 1 1 calc R . . C10 C 0.1710(5) 0.0937(3) 0.4020(3) 0.0282(10) Uani 1 1 d . . . H10 H 0.2143 0.1248 0.4458 0.034 Uiso 1 1 calc R . . C11 C 0.0278(14) 0.0373(8) 0.0918(7) 0.151(6) Uani 1 1 d . . . H11A H 0.0845 -0.0046 0.1010 0.226 Uiso 1 1 calc R . . H11B H 0.0344 0.0570 0.0329 0.226 Uiso 1 1 calc R . . H11C H -0.0667 0.0249 0.0956 0.226 Uiso 1 1 calc R . . C12 C 0.4836(6) 0.2978(3) 0.2842(6) 0.0517(18) Uani 1 1 d . . . C13 C 0.5493(7) 0.3023(3) 0.2049(7) 0.068(2) Uani 1 1 d . . . C14 C 0.6814(8) 0.3286(4) 0.2114(9) 0.087(3) Uani 1 1 d . . . H14 H 0.7266 0.3312 0.1604 0.105 Uiso 1 1 calc R . . C15 C 0.7462(8) 0.3512(4) 0.2952(10) 0.093(4) Uani 1 1 d . . . H15 H 0.8353 0.3695 0.2994 0.112 Uiso 1 1 calc R . . C16 C 0.6833(7) 0.3475(4) 0.3731(8) 0.088(3) Uani 1 1 d . . . H16 H 0.7295 0.3631 0.4286 0.106 Uiso 1 1 calc R . . C17 C 0.5478(6) 0.3196(3) 0.3667(7) 0.067(2) Uani 1 1 d . . . H17 H 0.5034 0.3163 0.4180 0.080 Uiso 1 1 calc R . . C18 C 0.5398(11) 0.2814(6) 0.0470(8) 0.119(5) Uani 1 1 d . . . H18A H 0.5643 0.3298 0.0354 0.179 Uiso 1 1 calc R . . H18B H 0.4773 0.2637 -0.0037 0.179 Uiso 1 1 calc R . . H18C H 0.6218 0.2525 0.0553 0.179 Uiso 1 1 calc R . . C19 C 0.5520(5) 0.1239(3) 0.2437(3) 0.0291(10) Uani 1 1 d . . . H19 H 0.5181 0.1683 0.2235 0.035 Uiso 1 1 calc R . . C20 C 0.4555(5) 0.0723(3) 0.2602(3) 0.0278(10) Uani 1 1 d . . . H20 H 0.3626 0.0847 0.2471 0.033 Uiso 1 1 calc R . . C21 C 0.4875(5) -0.0016(3) 0.2973(4) 0.0375(12) Uani 1 1 d . . . H21A H 0.5081 -0.0323 0.2484 0.045 Uiso 1 1 calc R . . H21B H 0.4063 -0.0206 0.3198 0.045 Uiso 1 1 calc R . . C22 C 0.6095(6) -0.0030(3) 0.3738(4) 0.0386(13) Uani 1 1 d . . . H22A H 0.6034 -0.0454 0.4104 0.046 Uiso 1 1 calc R . . H22B H 0.6951 -0.0055 0.3477 0.046 Uiso 1 1 calc R . . C23 C 0.6125(5) 0.0616(3) 0.4337(3) 0.0319(11) Uani 1 1 d . . . H23 H 0.5587 0.0606 0.4806 0.038 Uiso 1 1 calc R . . C24 C 0.6891(5) 0.1225(3) 0.4244(4) 0.0342(11) Uani 1 1 d . . . H24 H 0.6855 0.1586 0.4668 0.041 Uiso 1 1 calc R . . C25 C 0.7778(5) 0.1346(3) 0.3507(4) 0.0366(12) Uani 1 1 d . . . H25A H 0.8627 0.1076 0.3650 0.044 Uiso 1 1 calc R . . H25B H 0.8024 0.1847 0.3501 0.044 Uiso 1 1 calc R . . C26 C 0.7084(5) 0.1135(3) 0.2563(4) 0.0358(12) Uani 1 1 d . . . H26A H 0.7286 0.0639 0.2457 0.043 Uiso 1 1 calc R . . H26B H 0.7472 0.1418 0.2114 0.043 Uiso 1 1 calc R . . N1 N 0.1866(4) 0.1837(2) 0.2840(3) 0.0333(10) Uani 1 1 d . . . N2 N 0.3440(4) 0.2729(2) 0.2751(4) 0.0444(13) Uani 1 1 d . . . O1 O 0.0736(6) 0.0882(3) 0.1595(3) 0.0713(14) Uani 1 1 d . . . O2 O 0.4741(6) 0.2787(3) 0.1275(4) 0.0784(18) Uani 1 1 d . . . Cl1 Cl 0.43698(14) 0.19563(8) 0.51237(10) 0.0418(3) Uani 1 1 d . . . Rh1 Rh 0.47587(3) 0.146959(18) 0.36732(3) 0.02305(13) Uani 1 1 d . . . C27 C 0.0755(3) 0.4875(3) 0.5010(8) 0.123(4) Uani 1 1 d D . . H27A H 0.1185 0.5139 0.4563 0.147 Uiso 1 1 calc R . . H27B H 0.1270 0.4969 0.5604 0.147 Uiso 1 1 calc R . . C28 C 0.0805(7) 0.4092(3) 0.4807(6) 0.092(3) Uani 1 1 d D . . H28A H 0.0346 0.4007 0.4195 0.110 Uiso 1 1 calc R . . H28B H 0.0298 0.3835 0.5222 0.110 Uiso 1 1 calc R . . C29 C 0.2280(8) 0.3799(5) 0.4894(9) 0.170(7) Uani 1 1 d D . . H29A H 0.2251 0.3301 0.4743 0.255 Uiso 1 1 calc R . . H29B H 0.2726 0.3860 0.5507 0.255 Uiso 1 1 calc R . . H29C H 0.2789 0.4051 0.4487 0.255 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.025(2) 0.025(2) 0.039(3) 0.012(2) 0.014(2) 0.0036(18) C2 0.032(3) 0.049(4) 0.098(6) 0.040(4) -0.003(3) 0.006(3) C3 0.040(3) 0.033(3) 0.084(5) 0.012(3) -0.008(3) 0.008(2) C4 0.041(3) 0.042(3) 0.096(6) 0.039(4) 0.025(3) 0.019(3) C5 0.020(2) 0.025(2) 0.044(3) 0.006(2) 0.013(2) 0.0031(18) C6 0.033(3) 0.055(4) 0.038(3) 0.000(3) 0.014(2) 0.002(3) C7 0.045(3) 0.028(3) 0.081(5) -0.023(3) 0.018(3) -0.006(2) C8 0.039(3) 0.025(3) 0.070(4) 0.008(3) 0.019(3) 0.003(2) C9 0.032(3) 0.033(3) 0.051(4) 0.018(3) 0.010(2) 0.003(2) C10 0.025(2) 0.028(2) 0.033(3) 0.005(2) 0.006(2) 0.0029(19) C11 0.177(12) 0.227(16) 0.045(6) -0.044(8) 0.007(6) -0.078(11) C12 0.029(3) 0.022(3) 0.108(6) 0.021(3) 0.023(3) 0.002(2) C13 0.040(4) 0.033(3) 0.139(8) 0.038(4) 0.047(4) 0.010(3) C14 0.050(5) 0.045(4) 0.176(11) 0.044(6) 0.051(6) 0.008(4) C15 0.034(4) 0.042(4) 0.210(13) 0.033(6) 0.039(6) -0.004(3) C16 0.041(4) 0.034(4) 0.189(11) 0.003(5) 0.013(5) -0.004(3) C17 0.033(3) 0.025(3) 0.144(8) 0.013(4) 0.019(4) 0.005(2) C18 0.121(8) 0.115(8) 0.145(10) 0.065(8) 0.097(8) 0.047(7) C19 0.033(3) 0.030(2) 0.027(3) 0.005(2) 0.014(2) 0.006(2) C20 0.029(2) 0.031(3) 0.025(3) -0.008(2) 0.0105(19) 0.0066(19) C21 0.039(3) 0.021(2) 0.056(4) -0.007(2) 0.019(3) 0.001(2) C22 0.044(3) 0.021(2) 0.055(4) 0.011(2) 0.021(3) 0.010(2) C23 0.027(2) 0.038(3) 0.031(3) 0.014(2) 0.006(2) 0.012(2) C24 0.026(2) 0.036(3) 0.040(3) -0.002(2) 0.004(2) 0.005(2) C25 0.020(2) 0.039(3) 0.052(4) 0.001(2) 0.009(2) 0.001(2) C26 0.027(2) 0.037(3) 0.048(3) 0.006(2) 0.020(2) 0.003(2) N1 0.026(2) 0.025(2) 0.051(3) 0.0180(19) 0.0121(19) 0.0021(17) N2 0.031(2) 0.025(2) 0.081(4) 0.025(2) 0.020(2) 0.0072(18) O1 0.082(3) 0.092(4) 0.040(3) -0.003(3) 0.009(2) -0.014(3) O2 0.064(3) 0.075(4) 0.107(5) 0.058(3) 0.050(3) 0.020(3) Cl1 0.0385(7) 0.0439(7) 0.0448(8) -0.0179(6) 0.0121(6) -0.0046(6) Rh1 0.02156(19) 0.01825(18) 0.0307(2) 0.00164(15) 0.00836(14) 0.00239(14) C27 0.093(7) 0.130(10) 0.128(10) -0.003(8) -0.045(7) -0.003(7) C28 0.075(6) 0.141(9) 0.061(5) -0.021(6) 0.013(4) 0.025(6) C29 0.219(16) 0.194(15) 0.112(10) -0.064(10) 0.072(11) -0.129(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.336(6) . ? C1 N2 1.353(6) . ? C1 Rh1 2.034(5) . ? C2 C3 1.454(9) . ? C2 N1 1.484(7) . ? C3 C4 1.458(8) . ? C4 N2 1.481(7) . ? C5 C10 1.368(7) . ? C5 C6 1.398(8) . ? C5 N1 1.434(6) . ? C6 O1 1.359(7) . ? C6 C7 1.412(8) . ? C7 C8 1.357(9) . ? C8 C9 1.360(8) . ? C9 C10 1.385(7) . ? C11 O1 1.414(11) . ? C12 C17 1.359(11) . ? C12 C13 1.421(11) . ? C12 N2 1.429(7) . ? C13 O2 1.349(10) . ? C13 C14 1.372(10) . ? C14 C15 1.382(15) . ? C15 C16 1.386(15) . ? C16 C17 1.413(9) . ? C18 O2 1.436(9) . ? C19 C20 1.396(7) . ? C19 C26 1.525(7) . ? C19 Rh1 2.119(5) . ? C20 C21 1.509(7) . ? C20 Rh1 2.108(5) . ? C21 C22 1.528(8) . ? C22 C23 1.502(8) . ? C23 C24 1.383(7) . ? C23 Rh1 2.224(5) . ? C24 C25 1.505(7) . ? C24 Rh1 2.183(5) . ? C25 C26 1.522(8) . ? Cl1 Rh1 2.4191(14) . ? C27 C28 1.501(5) . ? C27 C27 1.543(5) 3_566 ? C28 C29 1.530(5) . ? 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 116.6(4) . . ? N1 C1 Rh1 124.5(3) . . ? N2 C1 Rh1 118.8(3) . . ? C3 C2 N1 109.9(5) . . ? C2 C3 C4 114.7(6) . . ? C3 C4 N2 110.8(5) . . ? C10 C5 C6 119.0(5) . . ? C10 C5 N1 122.3(5) . . ? C6 C5 N1 118.7(5) . . ? O1 C6 C5 116.7(5) . . ? O1 C6 C7 124.0(6) . . ? C5 C6 C7 119.3(5) . . ? C8 C7 C6 119.8(6) . . ? C7 C8 C9 120.8(5) . . ? C8 C9 C10 120.3(5) . . ? C5 C10 C9 120.8(5) . . ? C17 C12 C13 121.7(6) . . ? C17 C12 N2 119.9(6) . . ? C13 C12 N2 118.4(7) . . ? O2 C13 C14 124.9(9) . . ? O2 C13 C12 115.7(6) . . ? C14 C13 C12 119.4(10) . . ? C13 C14 C15 118.8(9) . . ? C14 C15 C16 122.5(7) . . ? C15 C16 C17 118.8(10) . . ? C12 C17 C16 118.8(8) . . ? C20 C19 C26 125.3(4) . . ? C20 C19 Rh1 70.3(3) . . ? C26 C19 Rh1 112.7(3) . . ? C19 C20 C21 126.3(4) . . ? C19 C20 Rh1 71.1(3) . . ? C21 C20 Rh1 110.0(3) . . ? C20 C21 C22 112.8(4) . . ? C23 C22 C21 112.1(4) . . ? C24 C23 C22 125.0(5) . . ? C24 C23 Rh1 70.1(3) . . ? C22 C23 Rh1 111.0(3) . . ? C23 C24 C25 124.9(5) . . ? C23 C24 Rh1 73.3(3) . . ? C25 C24 Rh1 107.4(4) . . ? C24 C25 C26 113.8(4) . . ? C25 C26 C19 112.9(4) . . ? C1 N1 C5 120.1(4) . . ? C1 N1 C2 125.0(4) . . ? C5 N1 C2 114.9(4) . . ? C1 N2 C12 119.7(4) . . ? C1 N2 C4 124.6(5) . . ? C12 N2 C4 115.6(4) . . ? C6 O1 C11 117.4(8) . . ? C13 O2 C18 116.5(7) . . ? C1 Rh1 C20 91.1(2) . . ? C1 Rh1 C19 92.01(19) . . ? C20 Rh1 C19 38.55(19) . . ? C1 Rh1 C24 156.81(19) . . ? C20 Rh1 C24 97.9(2) . . ? C19 Rh1 C24 82.1(2) . . ? C1 Rh1 C23 166.42(19) . . ? C20 Rh1 C23 81.0(2) . . ? C19 Rh1 C23 88.65(19) . . ? C24 Rh1 C23 36.55(19) . . ? C1 Rh1 Cl1 90.78(15) . . ? C20 Rh1 Cl1 155.97(14) . . ? C19 Rh1 Cl1 165.14(14) . . ? C24 Rh1 Cl1 89.60(15) . . ? C23 Rh1 Cl1 92.04(14) . . ? C28 C27 C27 110.6(5) . 3_566 ? C27 C28 C29 113.0(5) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.42 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.172 _refine_diff_density_min -1.464 _refine_diff_density_rms 0.131 # Attachment 'kjc0802.cif' data_kjc0802 _database_code_depnum_ccdc_archive 'CCDC 733096' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H38 Cl Ir N2 O, C4 H8 O' _chemical_formula_sum 'C33 H46 Cl Ir N2 O2' _chemical_formula_weight 730.37 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 0.0000 0.0000 '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 0.0060 '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' Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.5131(2) _cell_length_b 11.5515(2) _cell_length_c 14.2948(2) _cell_angle_alpha 80.8690(10) _cell_angle_beta 82.8800(10) _cell_angle_gamma 82.0440(10) _cell_volume 1527.65(5) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6108 _cell_measurement_theta_min 2.99 _cell_measurement_theta_max 27.51 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.588 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 736 _exptl_absorpt_coefficient_mu 4.489 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.3461 _exptl_absorpt_correction_T_max 0.6624 _exptl_absorpt_process_details DENZO _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'CCD scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25944 _diffrn_reflns_av_R_equivalents 0.0955 _diffrn_reflns_av_sigmaI/netI 0.0675 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 27.51 _reflns_number_total 6922 _reflns_number_gt 6108 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'cOLLECT,Nonius BV, 1997-2001' _computing_cell_refinement DENZO/SCALEPACK _computing_data_reduction DENZO/SCALEPACK _computing_structure_solution SHELXs-97 _computing_structure_refinement SHELXL-97 _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^)+(0.0512P)^2^+0.7944P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6922 _refine_ls_number_parameters 356 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0501 _refine_ls_R_factor_gt 0.0401 _refine_ls_wR_factor_ref 0.0999 _refine_ls_wR_factor_gt 0.0940 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1610(5) 0.3014(4) 0.7441(3) 0.0171(9) Uani 1 1 d . . . C2 C -0.0573(5) 0.1984(5) 0.7852(4) 0.0271(11) Uani 1 1 d . . . H2A H -0.1146 0.2769 0.7760 0.033 Uiso 1 1 calc R . . H2B H -0.0987 0.1531 0.8445 0.033 Uiso 1 1 calc R . . C3 C -0.0668(6) 0.1347(5) 0.7020(4) 0.0343(13) Uani 1 1 d . . . H3A H -0.1679 0.1392 0.6901 0.041 Uiso 1 1 calc R . . H3B H -0.0291 0.0504 0.7173 0.041 Uiso 1 1 calc R . . C4 C 0.0195(6) 0.1912(5) 0.6125(4) 0.0310(12) Uani 1 1 d . . . H4A H 0.1212 0.1583 0.6133 0.037 Uiso 1 1 calc R . . H4B H -0.0150 0.1712 0.5552 0.037 Uiso 1 1 calc R . . C5 C 0.0066(6) 0.3246(5) 0.6067(4) 0.0287(12) Uani 1 1 d . . . H5A H 0.0306 0.3594 0.5397 0.034 Uiso 1 1 calc R . . H5B H -0.0938 0.3545 0.6259 0.034 Uiso 1 1 calc R . . C6 C 0.1555(5) 0.1371(4) 0.8714(3) 0.0195(10) Uani 1 1 d . . . C7 C 0.0989(5) 0.1466(4) 0.9657(4) 0.0219(10) Uani 1 1 d . . . C8 C 0.1614(6) 0.0731(5) 1.0405(4) 0.0299(12) Uani 1 1 d . . . H8 H 0.1240 0.0791 1.1046 0.036 Uiso 1 1 calc R . . C9 C 0.2777(7) -0.0082(5) 1.0212(4) 0.0370(14) Uani 1 1 d . . . H9 H 0.3211 -0.0572 1.0722 0.044 Uiso 1 1 calc R . . C10 C 0.3313(6) -0.0191(5) 0.9289(4) 0.0367(14) Uani 1 1 d . . . H10 H 0.4101 -0.0766 0.9164 0.044 Uiso 1 1 calc R . . C11 C 0.2707(6) 0.0535(5) 0.8539(4) 0.0293(12) Uani 1 1 d . . . H11 H 0.3084 0.0459 0.7901 0.035 Uiso 1 1 calc R . . C12 C -0.0720(8) 0.2493(7) 1.0712(5) 0.0477(17) Uani 1 1 d . . . H12A H -0.1157 0.1791 1.1023 0.072 Uiso 1 1 calc R . . H12B H -0.1447 0.3183 1.0681 0.072 Uiso 1 1 calc R . . H12C H 0.0037 0.2621 1.1077 0.072 Uiso 1 1 calc R . . C13 C 0.1308(5) 0.4850(4) 0.6396(3) 0.0216(10) Uani 1 1 d . . . C14 C 0.2304(5) 0.5155(5) 0.5631(4) 0.0255(11) Uani 1 1 d . . . C15 C 0.2618(6) 0.6333(5) 0.5448(4) 0.0300(12) Uani 1 1 d . . . H15 H 0.3335 0.6549 0.4952 0.036 Uiso 1 1 calc R . . C16 C 0.1903(6) 0.7183(5) 0.5977(4) 0.0318(12) Uani 1 1 d . . . C17 C 0.0832(6) 0.6860(5) 0.6683(4) 0.0331(13) Uani 1 1 d . . . H17 H 0.0308 0.7446 0.7029 0.040 Uiso 1 1 calc R . . C18 C 0.0506(5) 0.5712(5) 0.6899(4) 0.0271(11) Uani 1 1 d . . . C19 C 0.3046(6) 0.4298(5) 0.4997(4) 0.0324(13) Uani 1 1 d . . . H19A H 0.3016 0.3491 0.5330 0.049 Uiso 1 1 calc R . . H19B H 0.4041 0.4448 0.4828 0.049 Uiso 1 1 calc R . . H19C H 0.2566 0.4394 0.4416 0.049 Uiso 1 1 calc R . . C20 C 0.2261(8) 0.8437(5) 0.5773(5) 0.0494(18) Uani 1 1 d . . . H20A H 0.2956 0.8522 0.5208 0.074 Uiso 1 1 calc R . . H20B H 0.2667 0.8624 0.6320 0.074 Uiso 1 1 calc R . . H20C H 0.1391 0.8979 0.5658 0.074 Uiso 1 1 calc R . . C21 C -0.0673(5) 0.5384(5) 0.7672(4) 0.0326(13) Uani 1 1 d . . . H21A H -0.1217 0.6104 0.7871 0.049 Uiso 1 1 calc R . . H21B H -0.0254 0.4901 0.8220 0.049 Uiso 1 1 calc R . . H21C H -0.1311 0.4934 0.7426 0.049 Uiso 1 1 calc R . . C22 C 0.5578(5) 0.4079(5) 0.7475(4) 0.0227(11) Uani 1 1 d . . . H22 H 0.5718 0.3855 0.6856 0.027 Uiso 1 1 calc R . . C23 C 0.5279(5) 0.5380(5) 0.7539(4) 0.0272(11) Uani 1 1 d . . . H23A H 0.5057 0.5813 0.6909 0.033 Uiso 1 1 calc R . . H23B H 0.6144 0.5658 0.7702 0.033 Uiso 1 1 calc R . . C24 C 0.4032(5) 0.5663(4) 0.8286(4) 0.0225(10) Uani 1 1 d . . . H24A H 0.4405 0.5631 0.8907 0.027 Uiso 1 1 calc R . . H24B H 0.3575 0.6477 0.8101 0.027 Uiso 1 1 calc R . . C25 C 0.2916(5) 0.4815(4) 0.8398(3) 0.0195(10) Uani 1 1 d . . . H25 H 0.2179 0.4999 0.7987 0.023 Uiso 1 1 calc R . . C26 C 0.2888(6) 0.3765(5) 0.9071(3) 0.0244(11) Uani 1 1 d . . . H26 H 0.2104 0.3329 0.9099 0.029 Uiso 1 1 calc R . . C27 C 0.4006(6) 0.3290(5) 0.9743(4) 0.0290(12) Uani 1 1 d . . . H27A H 0.3905 0.2452 0.9988 0.035 Uiso 1 1 calc R . . H27B H 0.3836 0.3733 1.0294 0.035 Uiso 1 1 calc R . . C28 C 0.5524(6) 0.3381(5) 0.9278(4) 0.0329(13) Uani 1 1 d . . . H28A H 0.5781 0.4175 0.9306 0.040 Uiso 1 1 calc R . . H28B H 0.6193 0.2791 0.9636 0.040 Uiso 1 1 calc R . . C29 C 0.5670(5) 0.3168(5) 0.8250(4) 0.0284(12) Uani 1 1 d . . . H29 H 0.5832 0.2375 0.8123 0.034 Uiso 1 1 calc R . . C30 C 0.6442(7) -0.1143(7) 0.7611(5) 0.0505(17) Uani 1 1 d . . . H30A H 0.6244 -0.0328 0.7768 0.061 Uiso 1 1 calc R . . H30B H 0.6291 -0.1701 0.8206 0.061 Uiso 1 1 calc R . . C31 C 0.5466(7) -0.1312(6) 0.6911(5) 0.0425(15) Uani 1 1 d . . . H31A H 0.5226 -0.2133 0.7014 0.051 Uiso 1 1 calc R . . H31B H 0.4574 -0.0761 0.6956 0.051 Uiso 1 1 calc R . . C32 C 0.6323(9) -0.1046(9) 0.5983(6) 0.065(2) Uani 1 1 d . . . H32A H 0.6147 -0.1564 0.5532 0.077 Uiso 1 1 calc R . . H32B H 0.6084 -0.0212 0.5701 0.077 Uiso 1 1 calc R . . C33 C 0.7807(8) -0.1269(8) 0.6196(5) 0.063(2) Uani 1 1 d . . . H33A H 0.8266 -0.2014 0.5974 0.075 Uiso 1 1 calc R . . H33B H 0.8336 -0.0618 0.5858 0.075 Uiso 1 1 calc R . . N1 N 0.0913(4) 0.2139(3) 0.7961(3) 0.0194(8) Uani 1 1 d . . . N2 N 0.0998(4) 0.3650(3) 0.6674(3) 0.0205(9) Uani 1 1 d . . . O1 O -0.0129(4) 0.2322(3) 0.9774(3) 0.0299(8) Uani 1 1 d . . . O2 O 0.7850(5) -0.1351(4) 0.7195(3) 0.0494(12) Uani 1 1 d . . . Cl1 Cl 0.45905(14) 0.20135(11) 0.65908(9) 0.0263(3) Uani 1 1 d . . . Ir1 Ir 0.358646(17) 0.331154(14) 0.770444(12) 0.01670(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.020(2) 0.020(2) 0.012(2) -0.0051(18) -0.0032(18) 0.0008(19) C2 0.014(2) 0.039(3) 0.028(3) 0.001(2) -0.002(2) -0.010(2) C3 0.033(3) 0.037(3) 0.036(3) -0.005(2) -0.006(3) -0.016(3) C4 0.036(3) 0.034(3) 0.028(3) -0.006(2) -0.011(2) -0.012(2) C5 0.028(3) 0.037(3) 0.023(3) -0.003(2) -0.014(2) -0.004(2) C6 0.019(2) 0.022(2) 0.017(2) 0.0026(18) -0.0006(19) -0.0065(19) C7 0.021(2) 0.021(2) 0.024(3) -0.003(2) 0.003(2) -0.008(2) C8 0.032(3) 0.037(3) 0.021(3) 0.003(2) -0.002(2) -0.013(2) C9 0.041(3) 0.036(3) 0.032(3) 0.016(2) -0.013(3) -0.012(3) C10 0.028(3) 0.034(3) 0.042(4) 0.008(3) 0.002(3) -0.001(2) C11 0.027(3) 0.030(3) 0.028(3) -0.002(2) 0.004(2) -0.003(2) C12 0.044(4) 0.058(4) 0.041(4) -0.019(3) 0.013(3) -0.008(3) C13 0.016(2) 0.027(3) 0.022(3) 0.001(2) -0.0045(19) -0.004(2) C14 0.021(3) 0.036(3) 0.019(3) 0.003(2) -0.007(2) -0.005(2) C15 0.030(3) 0.035(3) 0.024(3) 0.013(2) -0.009(2) -0.014(2) C16 0.033(3) 0.029(3) 0.033(3) 0.005(2) -0.015(2) -0.005(2) C17 0.032(3) 0.029(3) 0.039(3) -0.002(2) -0.012(3) -0.001(2) C18 0.018(3) 0.034(3) 0.027(3) 0.005(2) -0.011(2) 0.002(2) C19 0.026(3) 0.043(3) 0.023(3) 0.006(2) 0.003(2) -0.002(2) C20 0.057(4) 0.038(3) 0.058(4) 0.007(3) -0.029(4) -0.020(3) C21 0.015(3) 0.042(3) 0.040(3) -0.011(3) 0.004(2) -0.001(2) C22 0.011(2) 0.033(3) 0.027(3) -0.007(2) 0.0043(19) -0.013(2) C23 0.019(3) 0.030(3) 0.031(3) -0.002(2) 0.004(2) -0.010(2) C24 0.018(2) 0.024(2) 0.026(3) -0.001(2) -0.002(2) -0.007(2) C25 0.019(2) 0.022(2) 0.020(2) -0.0099(19) -0.0033(19) -0.0010(19) C26 0.026(3) 0.030(3) 0.020(3) -0.005(2) 0.001(2) -0.012(2) C27 0.040(3) 0.030(3) 0.020(3) -0.002(2) -0.008(2) -0.012(2) C28 0.033(3) 0.035(3) 0.033(3) 0.003(2) -0.019(2) -0.006(2) C29 0.017(3) 0.027(3) 0.043(3) -0.004(2) -0.012(2) -0.003(2) C30 0.046(4) 0.071(5) 0.030(3) -0.006(3) -0.001(3) 0.005(4) C31 0.042(4) 0.037(3) 0.048(4) -0.006(3) -0.002(3) -0.008(3) C32 0.056(5) 0.094(6) 0.044(4) -0.024(4) -0.003(4) 0.002(5) C33 0.051(5) 0.097(6) 0.029(4) 0.004(4) 0.000(3) 0.005(4) N1 0.015(2) 0.025(2) 0.019(2) -0.0005(16) -0.0015(16) -0.0082(17) N2 0.017(2) 0.024(2) 0.021(2) 0.0033(16) -0.0075(16) -0.0040(17) O1 0.027(2) 0.032(2) 0.030(2) -0.0079(16) 0.0083(16) -0.0057(16) O2 0.033(2) 0.072(3) 0.040(3) -0.009(2) -0.0027(19) 0.006(2) Cl1 0.0262(6) 0.0260(6) 0.0251(7) -0.0060(5) 0.0039(5) -0.0004(5) Ir1 0.01258(11) 0.02108(11) 0.01591(12) -0.00125(7) -0.00054(7) -0.00270(7) _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 1.356(6) . ? C1 N2 1.365(6) . ? C1 Ir1 2.048(5) . ? C2 N1 1.479(6) . ? C2 C3 1.512(7) . ? C3 C4 1.537(8) . ? C4 C5 1.519(8) . ? C5 N2 1.479(6) . ? C6 C11 1.383(7) . ? C6 C7 1.403(7) . ? C6 N1 1.425(6) . ? C7 O1 1.361(6) . ? C7 C8 1.395(7) . ? C8 C9 1.379(8) . ? C9 C10 1.373(8) . ? C10 C11 1.385(8) . ? C12 O1 1.421(7) . ? C13 C14 1.390(7) . ? C13 C18 1.404(7) . ? C13 N2 1.440(6) . ? C14 C15 1.410(8) . ? C14 C19 1.495(7) . ? C15 C16 1.386(8) . ? C16 C17 1.387(8) . ? C16 C20 1.509(8) . ? C17 C18 1.383(8) . ? C18 C21 1.517(7) . ? C22 C29 1.404(8) . ? C22 C23 1.505(7) . ? C22 Ir1 2.169(5) . ? C23 C24 1.531(7) . ? C24 C25 1.519(7) . ? C25 C26 1.425(7) . ? C25 Ir1 2.118(4) . ? C26 C27 1.510(7) . ? C26 Ir1 2.107(5) . ? C27 C28 1.523(8) . ? C28 C29 1.515(8) . ? C29 Ir1 2.195(5) . ? C30 O2 1.402(7) . ? C30 C31 1.497(9) . ? C31 C32 1.480(10) . ? C32 C33 1.460(11) . ? C33 O2 1.422(8) . ? Cl1 Ir1 2.3831(12) . ? 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 117.6(4) . . ? N1 C1 Ir1 122.4(3) . . ? N2 C1 Ir1 119.8(3) . . ? N1 C2 C3 112.4(4) . . ? C2 C3 C4 110.0(4) . . ? C5 C4 C3 111.7(5) . . ? N2 C5 C4 113.7(4) . . ? C11 C6 C7 119.5(5) . . ? C11 C6 N1 121.7(4) . . ? C7 C6 N1 118.7(4) . . ? O1 C7 C8 124.3(5) . . ? O1 C7 C6 116.1(4) . . ? C8 C7 C6 119.5(5) . . ? C9 C8 C7 119.8(5) . . ? C10 C9 C8 120.6(5) . . ? C9 C10 C11 120.2(5) . . ? C6 C11 C10 120.3(5) . . ? C14 C13 C18 121.1(5) . . ? C14 C13 N2 121.6(4) . . ? C18 C13 N2 117.2(4) . . ? C13 C14 C15 118.0(5) . . ? C13 C14 C19 123.1(5) . . ? C15 C14 C19 118.9(5) . . ? C16 C15 C14 121.5(5) . . ? C15 C16 C17 118.5(5) . . ? C15 C16 C20 120.6(6) . . ? C17 C16 C20 120.9(6) . . ? C18 C17 C16 122.0(5) . . ? C17 C18 C13 118.4(5) . . ? C17 C18 C21 120.9(5) . . ? C13 C18 C21 120.6(5) . . ? C29 C22 C23 125.8(5) . . ? C29 C22 Ir1 72.2(3) . . ? C23 C22 Ir1 109.5(3) . . ? C22 C23 C24 112.3(4) . . ? C25 C24 C23 112.8(4) . . ? C26 C25 C24 125.1(5) . . ? C26 C25 Ir1 69.8(3) . . ? C24 C25 Ir1 113.6(3) . . ? C25 C26 C27 125.2(5) . . ? C25 C26 Ir1 70.7(3) . . ? C27 C26 Ir1 110.2(3) . . ? C26 C27 C28 113.2(4) . . ? C29 C28 C27 111.1(4) . . ? C22 C29 C28 123.6(5) . . ? C22 C29 Ir1 70.2(3) . . ? C28 C29 Ir1 111.9(4) . . ? O2 C30 C31 108.0(5) . . ? C32 C31 C30 102.9(6) . . ? C33 C32 C31 105.2(6) . . ? O2 C33 C32 109.3(6) . . ? C1 N1 C6 120.4(4) . . ? C1 N1 C2 123.4(4) . . ? C6 N1 C2 116.0(4) . . ? C1 N2 C13 117.3(4) . . ? C1 N2 C5 127.6(4) . . ? C13 N2 C5 115.1(4) . . ? C7 O1 C12 119.0(5) . . ? C30 O2 C33 107.6(5) . . ? C1 Ir1 C26 94.44(19) . . ? C1 Ir1 C25 97.30(18) . . ? C26 Ir1 C25 39.43(19) . . ? C1 Ir1 C22 157.8(2) . . ? C26 Ir1 C22 98.13(19) . . ? C25 Ir1 C22 81.35(19) . . ? C1 Ir1 C29 164.2(2) . . ? C26 Ir1 C29 81.2(2) . . ? C25 Ir1 C29 89.0(2) . . ? C22 Ir1 C29 37.5(2) . . ? C1 Ir1 Cl1 88.04(13) . . ? C26 Ir1 Cl1 155.19(15) . . ? C25 Ir1 Cl1 164.30(14) . . ? C22 Ir1 Cl1 88.14(14) . . ? C29 Ir1 Cl1 89.73(15) . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 1.395 _refine_diff_density_min -2.100 _refine_diff_density_rms 0.184 # Attachment 'kjc0807.cif' data_1 _database_code_depnum_ccdc_archive 'CCDC 733097' _publ_section_exptl_refinement ; ? ; _publ_section_exptl_prep ; ? ; _cell_length_a 17.4487(3) _cell_length_b 10.4263(2) _cell_length_c 17.7256(4) _cell_angle_alpha 90 _cell_angle_beta 116.8549(9) _cell_angle_gamma 90 _cell_volume 2876.96(10) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Rh -1.1178 0.9187 19.2957 0.7515 14.3501 8.2176 4.7343 25.8749 1.2892 98.6062 5.3280 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 _chemical_formula_sum 'C31 H42 Cl1 N2 O1 Rh1' _chemical_formula_moiety 'C31 H42 Cl1 N2 O1 Rh1' _chemical_compound_source ? _chemical_formula_weight 597.05 _cell_measurement_reflns_used 52475 _cell_measurement_theta_min 3 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_min 0.08 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_max 0.20 _exptl_crystal_density_diffrn 1.378 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 0.712 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.87 _exptl_absorpt_correction_T_max 0.94 _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 47505 _reflns_number_total 12657 _diffrn_reflns_av_R_equivalents 0.075 _diffrn_reflns_theta_min 2.951 _diffrn_reflns_theta_max 27.472 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.472 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _reflns_limit_h_min -22 _reflns_limit_h_max 20 _reflns_limit_k_min -13 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 22 _atom_sites_solution_primary direct #heavy,direct,difmap,geom _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.77 _refine_diff_density_max 0.88 _refine_ls_number_reflns 12657 _refine_ls_number_restraints 0 _refine_ls_number_parameters 326 _refine_ls_wR_factor_ref 0.0974 _refine_ls_goodness_of_fit_ref 0.9621 _refine_ls_shift/su_max 0.002122 _refine_ls_R_factor_all 0.0721 _refine_ls_wR_factor_all 0.0974 _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 9779 _refine_ls_R_factor_gt 0.0470 _refine_ls_wR_factor_gt 0.0874 _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.02P)^2^ + 6.67P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens Rh1 Rh 0.549537(11) 0.629468(17) 0.234611(11) 0.0171 1.0000 Uani . . . . . . Cl2 Cl 0.60314(4) 0.66001(6) 0.38418(4) 0.0247 1.0000 Uani . . . . . . C3 C 0.51504(15) 0.6525(2) 0.10432(14) 0.0208 1.0000 Uani . . . . . . C4 C 0.50225(15) 0.5250(2) 0.12107(14) 0.0208 1.0000 Uani . . . . . . C5 C 0.55951(17) 0.4125(3) 0.12866(18) 0.0345 1.0000 Uani . . . . . . C6 C 0.65262(18) 0.4321(3) 0.18712(19) 0.0416 1.0000 Uani . . . . . . C7 C 0.66880(15) 0.5296(3) 0.25581(16) 0.0268 1.0000 Uani . . . . . . C8 C 0.67795(15) 0.6581(3) 0.24634(16) 0.0267 1.0000 Uani . . . . . . C9 C 0.66990(18) 0.7253(3) 0.16709(18) 0.0411 1.0000 Uani . . . . . . C10 C 0.59037(17) 0.6941(3) 0.08886(17) 0.0356 1.0000 Uani . . . . . . C11 C 0.43426(14) 0.6860(2) 0.22822(14) 0.0176 1.0000 Uani . . . . . . N12 N 0.42442(12) 0.81325(18) 0.23435(13) 0.0205 1.0000 Uani . . . . . . C13 C 0.47714(15) 0.9003(2) 0.21541(15) 0.0194 1.0000 Uani . . . . . . C14 C 0.55487(16) 0.9445(2) 0.27740(16) 0.0259 1.0000 Uani . . . . . . C15 C 0.60374(17) 1.0296(2) 0.25658(17) 0.0291 1.0000 Uani . . . . . . C16 C 0.57472(17) 1.0693(2) 0.17446(17) 0.0282 1.0000 Uani . . . . . . C17 C 0.49606(17) 1.0290(2) 0.11181(17) 0.0275 1.0000 Uani . . . . . . C18 C 0.44624(15) 0.9448(2) 0.13220(16) 0.0228 1.0000 Uani . . . . . . O19 O 0.36682(11) 0.90099(17) 0.07654(11) 0.0298 1.0000 Uani . . . . . . C20 C 0.3338(2) 0.9399(3) -0.00955(17) 0.0456 1.0000 Uani . . . . . . C21 C 0.35693(18) 0.8711(3) 0.2508(2) 0.0359 1.0000 Uani . . . . . . C22 C 0.33602(19) 0.7804(3) 0.30539(19) 0.0354 1.0000 Uani . . . . . . C23 C 0.31094(17) 0.6523(2) 0.26186(18) 0.0284 1.0000 Uani . . . . . . N24 N 0.37608(12) 0.60859(18) 0.23570(12) 0.0196 1.0000 Uani . . . . . . C25 C 0.36527(15) 0.4774(2) 0.20544(15) 0.0206 1.0000 Uani . . . . . . C26 C 0.40961(15) 0.3771(2) 0.26103(16) 0.0255 1.0000 Uani . . . . . . C27 C 0.39693(17) 0.2535(2) 0.22777(18) 0.0312 1.0000 Uani . . . . . . C28 C 0.34176(17) 0.2298(2) 0.14426(18) 0.0300 1.0000 Uani . . . . . . C29 C 0.29675(16) 0.3293(2) 0.09105(17) 0.0261 1.0000 Uani . . . . . . C30 C 0.30715(15) 0.4553(2) 0.12049(15) 0.0206 1.0000 Uani . . . . . . C31 C 0.25379(15) 0.5610(2) 0.06056(15) 0.0235 1.0000 Uani . . . . . . C32 C 0.26828(17) 0.5699(3) -0.01843(16) 0.0311 1.0000 Uani . . . . . . C33 C 0.15769(16) 0.5404(3) 0.03392(18) 0.0312 1.0000 Uani . . . . . . C34 C 0.46717(17) 0.3981(3) 0.35460(17) 0.0341 1.0000 Uani . . . . . . C35 C 0.5547(2) 0.3325(3) 0.3846(2) 0.0550 1.0000 Uani . . . . . . C36 C 0.4220(3) 0.3525(4) 0.4069(2) 0.0607 1.0000 Uani . . . . . . H31 H 0.4626 0.7059 0.0752 0.0254 1.0000 Uiso R . . . . . H41 H 0.4413 0.5001 0.1009 0.0252 1.0000 Uiso R . . . . . H51 H 0.5525 0.3885 0.0735 0.0373 1.0000 Uiso R . . . . . H52 H 0.5421 0.3401 0.1538 0.0381 1.0000 Uiso R . . . . . H61 H 0.6802 0.4634 0.1521 0.0440 1.0000 Uiso R . . . . . H62 H 0.6781 0.3510 0.2121 0.0434 1.0000 Uiso R . . . . . H71 H 0.6958 0.4947 0.3128 0.0310 1.0000 Uiso R . . . . . H81 H 0.7134 0.7055 0.2994 0.0323 1.0000 Uiso R . . . . . H92 H 0.7201 0.7059 0.1597 0.0500 1.0000 Uiso R . . . . . H91 H 0.6675 0.8195 0.1762 0.0507 1.0000 Uiso R . . . . . H101 H 0.5728 0.7667 0.0500 0.0440 1.0000 Uiso R . . . . . H102 H 0.6051 0.6219 0.0613 0.0446 1.0000 Uiso R . . . . . H141 H 0.5746 0.9175 0.3334 0.0309 1.0000 Uiso R . . . . . H151 H 0.6572 1.0595 0.2988 0.0361 1.0000 Uiso R . . . . . H161 H 0.6093 1.1257 0.1611 0.0364 1.0000 Uiso R . . . . . H171 H 0.4765 1.0579 0.0562 0.0355 1.0000 Uiso R . . . . . H203 H 0.2773 0.9039 -0.0394 0.0639 1.0000 Uiso R . . . . . H201 H 0.3314 1.0325 -0.0124 0.0642 1.0000 Uiso R . . . . . H202 H 0.3705 0.9057 -0.0324 0.0639 1.0000 Uiso R . . . . . H211 H 0.3775 0.9530 0.2798 0.0482 1.0000 Uiso R . . . . . H212 H 0.3048 0.8849 0.1975 0.0480 1.0000 Uiso R . . . . . H221 H 0.3860 0.7701 0.3600 0.0499 1.0000 Uiso R . . . . . H222 H 0.2880 0.8145 0.3132 0.0499 1.0000 Uiso R . . . . . H231 H 0.3048 0.5880 0.2992 0.0431 1.0000 Uiso R . . . . . H232 H 0.2559 0.6626 0.2106 0.0430 1.0000 Uiso R . . . . . H271 H 0.4270 0.1845 0.2638 0.0388 1.0000 Uiso R . . . . . H281 H 0.3349 0.1460 0.1231 0.0360 1.0000 Uiso R . . . . . H291 H 0.2585 0.3120 0.0341 0.0331 1.0000 Uiso R . . . . . H311 H 0.2704 0.6433 0.0900 0.0285 1.0000 Uiso R . . . . . H322 H 0.2315 0.6367 -0.0552 0.0460 1.0000 Uiso R . . . . . H321 H 0.3280 0.5895 -0.0021 0.0459 1.0000 Uiso R . . . . . H323 H 0.2538 0.4875 -0.0472 0.0459 1.0000 Uiso R . . . . . H333 H 0.1244 0.6103 -0.0014 0.0469 1.0000 Uiso R . . . . . H331 H 0.1482 0.5365 0.0836 0.0470 1.0000 Uiso R . . . . . H332 H 0.1388 0.4607 0.0032 0.0468 1.0000 Uiso R . . . . . H341 H 0.4775 0.4902 0.3635 0.0398 1.0000 Uiso R . . . . . H351 H 0.5907 0.3568 0.4417 0.0651 1.0000 Uiso R . . . . . H353 H 0.5813 0.3603 0.3493 0.0655 1.0000 Uiso R . . . . . H352 H 0.5467 0.2403 0.3809 0.0650 1.0000 Uiso R . . . . . H362 H 0.4573 0.3712 0.4658 0.0929 1.0000 Uiso R . . . . . H361 H 0.3669 0.3956 0.3871 0.0932 1.0000 Uiso R . . . . . H363 H 0.4124 0.2609 0.3989 0.0930 1.0000 Uiso R . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Rh1 0.01585(10) 0.01855(10) 0.01678(11) -0.00073(8) 0.00728(7) 0.00049(8) Cl2 0.0259(3) 0.0278(3) 0.0188(3) -0.0013(2) 0.0086(2) -0.0014(2) C3 0.0198(12) 0.0287(14) 0.0130(12) 0.0005(10) 0.0066(10) 0.0000(10) C4 0.0192(12) 0.0267(13) 0.0132(12) -0.0065(10) 0.0044(10) -0.0013(10) C5 0.0332(15) 0.0297(14) 0.0325(16) -0.0084(12) 0.0078(12) 0.0079(12) C6 0.0311(15) 0.0444(18) 0.0378(17) -0.0095(14) 0.0055(13) 0.0141(13) C7 0.0160(12) 0.0362(15) 0.0246(14) -0.0014(11) 0.0061(10) 0.0075(10) C8 0.0127(11) 0.0425(17) 0.0230(13) -0.0025(11) 0.0065(10) -0.0054(10) C9 0.0248(14) 0.063(2) 0.0370(17) 0.0080(15) 0.0154(13) -0.0087(14) C10 0.0302(15) 0.0476(18) 0.0288(15) 0.0086(13) 0.0132(12) -0.0060(13) C11 0.0164(11) 0.0222(12) 0.0118(11) 0.0004(9) 0.0043(9) 0.0004(9) N12 0.0206(10) 0.0183(10) 0.0269(11) -0.0007(8) 0.0145(9) 0.0014(8) C13 0.0211(12) 0.0149(11) 0.0246(13) 0.0005(9) 0.0124(10) 0.0020(9) C14 0.0266(13) 0.0216(13) 0.0257(14) 0.0003(10) 0.0085(11) 0.0009(10) C15 0.0241(13) 0.0243(13) 0.0356(16) -0.0038(11) 0.0104(12) -0.0033(11) C16 0.0304(14) 0.0205(13) 0.0401(16) 0.0000(11) 0.0215(13) -0.0039(11) C17 0.0312(14) 0.0252(13) 0.0285(15) 0.0038(11) 0.0157(12) -0.0001(11) C18 0.0203(12) 0.0210(12) 0.0269(14) -0.0008(10) 0.0104(11) 0.0007(10) O19 0.0220(9) 0.0380(11) 0.0235(10) 0.0024(8) 0.0050(8) -0.0065(8) C20 0.0376(17) 0.066(2) 0.0234(16) 0.0040(15) 0.0049(13) -0.0084(15) C21 0.0380(15) 0.0257(14) 0.0598(19) -0.0030(14) 0.0360(15) 0.0014(12) C22 0.0414(16) 0.0336(15) 0.0488(18) -0.0083(13) 0.0358(15) -0.0059(13) C23 0.0319(14) 0.0272(14) 0.0392(16) -0.0032(11) 0.0276(13) -0.0027(11) N24 0.0216(10) 0.0196(10) 0.0226(11) -0.0016(8) 0.0144(9) -0.0005(8) C25 0.0227(12) 0.0178(12) 0.0261(13) 0.0018(10) 0.0152(11) 0.0005(9) C26 0.0221(12) 0.0262(13) 0.0303(14) 0.0036(11) 0.0137(11) -0.0039(11) C27 0.0292(14) 0.0219(13) 0.0443(17) 0.0079(12) 0.0183(13) 0.0038(11) C28 0.0289(14) 0.0193(13) 0.0455(18) -0.0057(12) 0.0201(13) -0.0016(11) C29 0.0286(13) 0.0253(13) 0.0282(14) -0.0061(11) 0.0161(12) -0.0031(10) C30 0.0217(12) 0.0211(12) 0.0252(13) 0.0000(10) 0.0161(11) -0.0012(10) C31 0.0227(12) 0.0252(13) 0.0213(13) 0.0004(10) 0.0088(10) 0.0003(10) C32 0.0261(13) 0.0438(17) 0.0245(14) 0.0082(12) 0.0123(11) 0.0055(12) C33 0.0266(14) 0.0336(15) 0.0369(16) 0.0049(12) 0.0174(12) 0.0061(11) C34 0.0339(15) 0.0315(15) 0.0296(15) 0.0093(12) 0.0079(12) -0.0060(12) C35 0.0410(18) 0.0388(18) 0.055(2) 0.0126(16) -0.0047(16) 0.0020(14) C36 0.074(3) 0.072(3) 0.0341(18) 0.0089(17) 0.0223(18) -0.028(2) _refine_ls_extinction_coef 181(12) _refine_ls_extinction_method 'Larson (1970), Equation 22' loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Rh1 . Cl2 . 2.4010(6) yes Rh1 . C3 . 2.121(2) yes Rh1 . C4 . 2.102(2) yes Rh1 . C7 . 2.202(2) yes Rh1 . C8 . 2.175(2) yes Rh1 . C11 . 2.049(2) yes C3 . C4 . 1.402(3) yes C3 . C10 . 1.522(3) yes C3 . H31 . 0.993 no C4 . C5 . 1.507(3) yes C4 . H41 . 0.991 no C5 . C6 . 1.495(4) yes C5 . H51 . 0.962 no C5 . H52 . 0.990 no C6 . C7 . 1.511(4) yes C6 . H61 . 0.996 no C6 . H62 . 0.965 no C7 . C8 . 1.369(4) yes C7 . H71 . 0.972 no C8 . C9 . 1.518(4) yes C8 . H81 . 0.993 no C9 . C10 . 1.488(4) yes C9 . H92 . 0.964 no C9 . H91 . 1.000 no C10 . H101 . 0.975 no C10 . H102 . 0.993 no C11 . N12 . 1.349(3) yes C11 . N24 . 1.349(3) yes N12 . C13 . 1.436(3) yes N12 . C21 . 1.465(3) yes C13 . C14 . 1.383(3) yes C13 . C18 . 1.401(3) yes C14 . C15 . 1.391(4) yes C14 . H141 . 0.935 no C15 . C16 . 1.372(4) yes C15 . H151 . 0.947 no C16 . C17 . 1.384(4) yes C16 . H161 . 0.946 no C17 . C18 . 1.393(3) yes C17 . H171 . 0.935 no C18 . O19 . 1.367(3) yes O19 . C20 . 1.425(3) yes C20 . H203 . 0.961 no C20 . H201 . 0.968 no C20 . H202 . 0.966 no C21 . C22 . 1.511(4) yes C21 . H211 . 0.978 no C21 . H212 . 0.982 no C22 . C23 . 1.505(4) yes C22 . H221 . 0.973 no C22 . H222 . 0.976 no C23 . N24 . 1.480(3) yes C23 . H231 . 0.981 no C23 . H232 . 0.986 no N24 . C25 . 1.450(3) yes C25 . C26 . 1.405(3) yes C25 . C30 . 1.403(3) yes C26 . C27 . 1.393(4) yes C26 . C34 . 1.518(4) yes C27 . C28 . 1.375(4) yes C27 . H271 . 0.947 no C28 . C29 . 1.384(4) yes C28 . H281 . 0.936 no C29 . C30 . 1.395(3) yes C29 . H291 . 0.943 no C30 . C31 . 1.522(3) yes C31 . C32 . 1.534(3) yes C31 . C33 . 1.538(3) yes C31 . H311 . 0.978 no C32 . H322 . 0.972 no C32 . H321 . 0.970 no C32 . H323 . 0.973 no C33 . H333 . 0.965 no C33 . H331 . 0.967 no C33 . H332 . 0.966 no C34 . C35 . 1.534(4) yes C34 . C36 . 1.538(4) yes C34 . H341 . 0.976 no C35 . H351 . 0.953 no C35 . H353 . 0.975 no C35 . H352 . 0.969 no C36 . H362 . 0.963 no C36 . H361 . 0.971 no C36 . H363 . 0.969 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag Cl2 . Rh1 . C3 . 164.75(7) yes Cl2 . Rh1 . C4 . 156.16(7) yes C3 . Rh1 . C4 . 38.78(9) yes Cl2 . Rh1 . C7 . 90.44(7) yes C3 . Rh1 . C7 . 91.19(9) yes C4 . Rh1 . C7 . 81.38(9) yes Cl2 . Rh1 . C8 . 90.32(7) yes C3 . Rh1 . C8 . 82.07(9) yes C4 . Rh1 . C8 . 95.99(10) yes C7 . Rh1 . C8 . 36.43(10) yes Cl2 . Rh1 . C11 . 84.60(6) yes C3 . Rh1 . C11 . 96.81(9) yes C4 . Rh1 . C11 . 98.35(9) yes C7 . Rh1 . C11 . 166.80(10) yes C8 . Rh1 . C11 . 155.33(10) yes Rh1 . C3 . C4 . 69.88(13) yes Rh1 . C3 . C10 . 112.65(16) yes C4 . C3 . C10 . 122.8(2) yes Rh1 . C3 . H31 . 111.8 no C4 . C3 . H31 . 116.3 no C10 . C3 . H31 . 114.5 no C3 . C4 . Rh1 . 71.34(13) yes C3 . C4 . C5 . 126.5(2) yes Rh1 . C4 . C5 . 111.12(16) yes C3 . C4 . H41 . 114.8 no Rh1 . C4 . H41 . 112.0 no C5 . C4 . H41 . 112.9 no C4 . C5 . C6 . 115.1(2) yes C4 . C5 . H51 . 109.6 no C6 . C5 . H51 . 109.8 no C4 . C5 . H52 . 107.9 no C6 . C5 . H52 . 104.5 no H51 . C5 . H52 . 109.6 no C5 . C6 . C7 . 113.6(2) yes C5 . C6 . H61 . 107.1 no C7 . C6 . H61 . 108.4 no C5 . C6 . H62 . 109.2 no C7 . C6 . H62 . 109.8 no H61 . C6 . H62 . 108.7 no C6 . C7 . Rh1 . 111.24(16) yes C6 . C7 . C8 . 123.3(3) yes Rh1 . C7 . C8 . 70.71(14) yes C6 . C7 . H71 . 114.3 no Rh1 . C7 . H71 . 109.3 no C8 . C7 . H71 . 117.7 no Rh1 . C8 . C7 . 72.86(14) yes Rh1 . C8 . C9 . 108.30(16) yes C7 . C8 . C9 . 126.7(3) yes Rh1 . C8 . H81 . 109.5 no C7 . C8 . H81 . 115.4 no C9 . C8 . H81 . 113.8 no C8 . C9 . C10 . 114.8(2) yes C8 . C9 . H92 . 108.6 no C10 . C9 . H92 . 110.5 no C8 . C9 . H91 . 107.3 no C10 . C9 . H91 . 106.0 no H92 . C9 . H91 . 109.6 no C3 . C10 . C9 . 114.3(2) yes C3 . C10 . H101 . 109.1 no C9 . C10 . H101 . 110.6 no C3 . C10 . H102 . 108.0 no C9 . C10 . H102 . 106.5 no H101 . C10 . H102 . 108.1 no Rh1 . C11 . N12 . 115.85(16) yes Rh1 . C11 . N24 . 125.86(17) yes N12 . C11 . N24 . 116.8(2) yes C11 . N12 . C13 . 118.99(19) yes C11 . N12 . C21 . 124.4(2) yes C13 . N12 . C21 . 116.35(19) yes N12 . C13 . C14 . 121.8(2) yes N12 . C13 . C18 . 118.2(2) yes C14 . C13 . C18 . 119.9(2) yes C13 . C14 . C15 . 120.0(2) yes C13 . C14 . H141 . 120.1 no C15 . C14 . H141 . 119.9 no C14 . C15 . C16 . 119.8(2) yes C14 . C15 . H151 . 120.2 no C16 . C15 . H151 . 119.9 no C15 . C16 . C17 . 121.1(2) yes C15 . C16 . H161 . 118.8 no C17 . C16 . H161 . 120.1 no C16 . C17 . C18 . 119.5(2) yes C16 . C17 . H171 . 120.3 no C18 . C17 . H171 . 120.2 no C13 . C18 . C17 . 119.6(2) yes C13 . C18 . O19 . 115.6(2) yes C17 . C18 . O19 . 124.9(2) yes C18 . O19 . C20 . 117.7(2) yes O19 . C20 . H203 . 107.2 no O19 . C20 . H201 . 109.1 no H203 . C20 . H201 . 110.6 no O19 . C20 . H202 . 108.7 no H203 . C20 . H202 . 109.6 no H201 . C20 . H202 . 111.6 no N12 . C21 . C22 . 108.5(2) yes N12 . C21 . H211 . 109.1 no C22 . C21 . H211 . 110.3 no N12 . C21 . H212 . 110.3 no C22 . C21 . H212 . 108.7 no H211 . C21 . H212 . 109.8 no C21 . C22 . C23 . 109.0(2) yes C21 . C22 . H221 . 109.8 no C23 . C22 . H221 . 109.6 no C21 . C22 . H222 . 109.5 no C23 . C22 . H222 . 109.1 no H221 . C22 . H222 . 109.9 no C22 . C23 . N24 . 110.3(2) yes C22 . C23 . H231 . 110.8 no N24 . C23 . H231 . 109.5 no C22 . C23 . H232 . 108.2 no N24 . C23 . H232 . 108.1 no H231 . C23 . H232 . 109.9 no C23 . N24 . C11 . 124.39(19) yes C23 . N24 . C25 . 114.60(18) yes C11 . N24 . C25 . 120.37(19) yes N24 . C25 . C26 . 120.3(2) yes N24 . C25 . C30 . 117.5(2) yes C26 . C25 . C30 . 122.2(2) yes C25 . C26 . C27 . 117.4(2) yes C25 . C26 . C34 . 122.8(2) yes C27 . C26 . C34 . 119.8(2) yes C26 . C27 . C28 . 121.5(2) yes C26 . C27 . H271 . 118.9 no C28 . C27 . H271 . 119.6 no C27 . C28 . C29 . 120.3(2) yes C27 . C28 . H281 . 119.9 no C29 . C28 . H281 . 119.7 no C28 . C29 . C30 . 120.9(2) yes C28 . C29 . H291 . 119.7 no C30 . C29 . H291 . 119.4 no C25 . C30 . C29 . 117.7(2) yes C25 . C30 . C31 . 123.2(2) yes C29 . C30 . C31 . 119.1(2) yes C30 . C31 . C32 . 112.3(2) yes C30 . C31 . C33 . 110.6(2) yes C32 . C31 . C33 . 109.5(2) yes C30 . C31 . H311 . 108.8 no C32 . C31 . H311 . 107.6 no C33 . C31 . H311 . 107.8 no C31 . C32 . H322 . 108.9 no C31 . C32 . H321 . 109.8 no H322 . C32 . H321 . 110.1 no C31 . C32 . H323 . 108.3 no H322 . C32 . H323 . 110.2 no H321 . C32 . H323 . 109.5 no C31 . C33 . H333 . 110.3 no C31 . C33 . H331 . 109.8 no H333 . C33 . H331 . 108.7 no C31 . C33 . H332 . 109.9 no H333 . C33 . H332 . 109.3 no H331 . C33 . H332 . 108.8 no C26 . C34 . C35 . 112.2(3) yes C26 . C34 . C36 . 110.3(2) yes C35 . C34 . C36 . 110.8(3) yes C26 . C34 . H341 . 107.6 no C35 . C34 . H341 . 107.5 no C36 . C34 . H341 . 108.3 no C34 . C35 . H351 . 108.9 no C34 . C35 . H353 . 109.4 no H351 . C35 . H353 . 109.0 no C34 . C35 . H352 . 109.2 no H351 . C35 . H352 . 109.9 no H353 . C35 . H352 . 110.4 no C34 . C36 . H362 . 109.8 no C34 . C36 . H361 . 109.3 no H362 . C36 . H361 . 110.0 no C34 . C36 . H363 . 108.6 no H362 . C36 . H363 . 110.0 no H361 . C36 . H363 . 109.1 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C4 . H41 . C30 . 154 0.99 2.56 3.476(4) yes # Attachment 'kjc0810.cif' data_kjc0810 _database_code_depnum_ccdc_archive 'CCDC 733098' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H31 N2 S, Br' _chemical_formula_sum 'C23 H31 Br N2 S' _chemical_formula_weight 447.47 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 0.0000 0.0000 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.00230(10) _cell_length_b 14.4043(2) _cell_length_c 17.6548(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.7000(10) _cell_angle_gamma 90.00 _cell_volume 2268.69(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3819 _cell_measurement_theta_min 3.05 _cell_measurement_theta_max 27.54 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.310 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 1.914 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7008 _exptl_absorpt_correction_T_max 0.8317 _exptl_absorpt_process_details Denzo/Scalepack _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'CCD scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 37229 _diffrn_reflns_av_R_equivalents 0.2138 _diffrn_reflns_av_sigmaI/netI 0.0995 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 27.54 _reflns_number_total 5195 _reflns_number_gt 3819 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'cOLLECT,Nonius BV, 1997-2001' _computing_cell_refinement DENZO/SCALEPACK _computing_data_reduction DENZO/SCALEPACK _computing_structure_solution SHELXs-97 _computing_structure_refinement SHELXL-97 _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^)+(0.0461P)^2^+2.3410P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5195 _refine_ls_number_parameters 249 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0859 _refine_ls_R_factor_gt 0.0585 _refine_ls_wR_factor_ref 0.1498 _refine_ls_wR_factor_gt 0.1346 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.18589(5) 0.61480(3) 0.64878(2) 0.04313(16) Uani 1 1 d . . . S2 S 0.31060(9) 0.60867(7) 0.37840(6) 0.0335(2) Uani 1 1 d . . . C3 C 0.4857(4) 0.6247(2) 0.4343(2) 0.0249(7) Uani 1 1 d . . . C4 C 0.6092(3) 0.6364(2) 0.39415(19) 0.0229(7) Uani 1 1 d . . . N5 N 0.5822(3) 0.64543(18) 0.31258(15) 0.0219(6) Uani 1 1 d . . . C6 C 0.6204(3) 0.5779(2) 0.26808(18) 0.0208(6) Uani 1 1 d . . . H6 H 0.6680 0.5244 0.2917 0.025 Uiso 1 1 calc R . . N7 N 0.5960(3) 0.58082(17) 0.19325(15) 0.0204(5) Uani 1 1 d . . . C8 C 0.6570(3) 0.5100(2) 0.14825(17) 0.0216(6) Uani 1 1 d . . . C9 C 0.8041(3) 0.5216(2) 0.13136(18) 0.0247(7) Uani 1 1 d . . . C10 C 0.8570(4) 0.4539(2) 0.08497(19) 0.0283(7) Uani 1 1 d . . . H10 H 0.9555 0.4593 0.0718 0.034 Uiso 1 1 calc R . . C11 C 0.7702(4) 0.3800(2) 0.0581(2) 0.0321(8) Uani 1 1 d . . . H11 H 0.8091 0.3352 0.0265 0.038 Uiso 1 1 calc R . . C12 C 0.6265(4) 0.3696(2) 0.0764(2) 0.0307(8) Uani 1 1 d . . . H12 H 0.5682 0.3175 0.0575 0.037 Uiso 1 1 calc R . . C13 C 0.5662(4) 0.4347(2) 0.12213(19) 0.0260(7) Uani 1 1 d . . . C14 C 0.4122(4) 0.4205(3) 0.1464(2) 0.0334(8) Uani 1 1 d . . . H14 H 0.3787 0.4813 0.1656 0.040 Uiso 1 1 calc R . . C15 C 0.2959(4) 0.3898(3) 0.0801(3) 0.0477(11) Uani 1 1 d . . . H15A H 0.2909 0.4356 0.0388 0.072 Uiso 1 1 calc R . . H15B H 0.1975 0.3847 0.0978 0.072 Uiso 1 1 calc R . . H15C H 0.3246 0.3293 0.0612 0.072 Uiso 1 1 calc R . . C17 C 0.4201(5) 0.3507(4) 0.2119(3) 0.0617(13) Uani 1 1 d . . . H17A H 0.4504 0.2900 0.1943 0.093 Uiso 1 1 calc R . . H17B H 0.3214 0.3456 0.2292 0.093 Uiso 1 1 calc R . . H17C H 0.4936 0.3719 0.2544 0.093 Uiso 1 1 calc R . . C18 C 0.9029(4) 0.6007(2) 0.1631(2) 0.0322(8) Uani 1 1 d . . . H18 H 0.8378 0.6469 0.1853 0.039 Uiso 1 1 calc R . . C19 C 1.0194(5) 0.5665(3) 0.2281(3) 0.0554(12) Uani 1 1 d . . . H19A H 0.9686 0.5359 0.2670 0.083 Uiso 1 1 calc R . . H19B H 1.0774 0.6194 0.2511 0.083 Uiso 1 1 calc R . . H19C H 1.0870 0.5223 0.2079 0.083 Uiso 1 1 calc R . . C20 C 0.9791(5) 0.6505(3) 0.1039(3) 0.0546(12) Uani 1 1 d . . . H20A H 1.0465 0.6074 0.0822 0.082 Uiso 1 1 calc R . . H20B H 1.0370 0.7029 0.1277 0.082 Uiso 1 1 calc R . . H20C H 0.9034 0.6734 0.0631 0.082 Uiso 1 1 calc R . . C21 C 0.5165(3) 0.6591(2) 0.15131(18) 0.0249(7) Uani 1 1 d . . . H21A H 0.4505 0.6351 0.1062 0.030 Uiso 1 1 calc R . . H21B H 0.5902 0.7018 0.1331 0.030 Uiso 1 1 calc R . . C22 C 0.4235(3) 0.7112(2) 0.2026(2) 0.0277(7) Uani 1 1 d . . . H22A H 0.3358 0.6732 0.2113 0.033 Uiso 1 1 calc R . . H22B H 0.3863 0.7697 0.1774 0.033 Uiso 1 1 calc R . . C23 C 0.5169(4) 0.7328(2) 0.27822(19) 0.0255(7) Uani 1 1 d . . . H23A H 0.5980 0.7766 0.2703 0.031 Uiso 1 1 calc R . . H23B H 0.4534 0.7622 0.3131 0.031 Uiso 1 1 calc R . . C24 C 0.7535(4) 0.6408(2) 0.4319(2) 0.0284(7) Uani 1 1 d . . . H24 H 0.8354 0.6472 0.4036 0.034 Uiso 1 1 calc R . . C25 C 0.7797(4) 0.6359(2) 0.5112(2) 0.0326(8) Uani 1 1 d . . . H25 H 0.8790 0.6381 0.5373 0.039 Uiso 1 1 calc R . . C26 C 0.6580(4) 0.6277(2) 0.5514(2) 0.0314(8) Uani 1 1 d . . . H26 H 0.6744 0.6263 0.6057 0.038 Uiso 1 1 calc R . . C27 C 0.5129(4) 0.6214(2) 0.5137(2) 0.0298(8) Uani 1 1 d . . . H27 H 0.4314 0.6147 0.5424 0.036 Uiso 1 1 calc R . . C28 C 0.1814(4) 0.6006(3) 0.4478(2) 0.0408(9) Uani 1 1 d . . . H28A H 0.2197 0.5561 0.4876 0.061 Uiso 1 1 calc R . . H28B H 0.0836 0.5797 0.4225 0.061 Uiso 1 1 calc R . . H28C H 0.1708 0.6617 0.4709 0.061 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.0590(3) 0.0412(3) 0.0305(2) 0.00556(17) 0.01108(18) 0.02528(17) S2 0.0282(4) 0.0466(6) 0.0263(5) 0.0048(4) 0.0057(3) 0.0013(4) C3 0.0303(16) 0.0218(16) 0.0227(18) 0.0006(13) 0.0039(13) 0.0033(13) C4 0.0330(16) 0.0170(15) 0.0189(17) -0.0001(13) 0.0043(13) 0.0057(13) N5 0.0264(13) 0.0195(13) 0.0202(14) 0.0013(11) 0.0045(10) 0.0033(10) C6 0.0203(14) 0.0201(16) 0.0223(17) 0.0001(14) 0.0041(12) -0.0013(12) N7 0.0242(12) 0.0189(13) 0.0180(14) -0.0012(11) 0.0028(10) 0.0000(10) C8 0.0302(16) 0.0197(16) 0.0152(15) -0.0012(13) 0.0042(12) 0.0013(12) C9 0.0256(15) 0.0275(17) 0.0209(17) 0.0024(14) 0.0029(12) 0.0004(13) C10 0.0320(17) 0.0297(18) 0.0247(18) 0.0015(15) 0.0090(14) 0.0047(14) C11 0.047(2) 0.0239(18) 0.028(2) -0.0021(15) 0.0149(16) 0.0061(15) C12 0.0404(18) 0.0228(17) 0.030(2) -0.0074(15) 0.0083(15) -0.0037(14) C13 0.0317(16) 0.0216(16) 0.0253(18) -0.0001(14) 0.0055(13) -0.0007(13) C14 0.0333(18) 0.0297(19) 0.039(2) -0.0079(17) 0.0102(15) -0.0083(15) C15 0.034(2) 0.047(2) 0.060(3) -0.002(2) -0.0035(19) -0.0040(17) C17 0.043(2) 0.091(4) 0.051(3) 0.018(3) 0.005(2) -0.030(2) C18 0.0257(16) 0.037(2) 0.035(2) -0.0057(16) 0.0061(14) -0.0055(14) C19 0.046(2) 0.071(3) 0.044(3) 0.005(2) -0.0116(19) -0.024(2) C20 0.068(3) 0.053(3) 0.042(3) 0.006(2) 0.005(2) -0.031(2) C21 0.0312(16) 0.0231(16) 0.0195(17) 0.0029(14) 0.0007(13) -0.0007(13) C22 0.0283(16) 0.0289(18) 0.0261(19) 0.0051(15) 0.0041(13) 0.0080(13) C23 0.0345(17) 0.0203(16) 0.0229(18) 0.0024(14) 0.0084(13) 0.0057(13) C24 0.0277(16) 0.0263(17) 0.031(2) -0.0022(15) 0.0037(14) 0.0050(14) C25 0.0401(19) 0.0259(18) 0.029(2) -0.0022(15) -0.0055(15) 0.0009(15) C26 0.050(2) 0.0257(18) 0.0179(18) -0.0009(14) 0.0013(15) 0.0027(15) C27 0.0432(19) 0.0267(18) 0.0206(18) -0.0003(14) 0.0083(15) 0.0023(14) C28 0.0368(19) 0.051(2) 0.038(2) 0.0090(19) 0.0180(17) 0.0056(17) _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 S2 C3 1.759(3) . ? S2 C28 1.802(4) . ? C3 C27 1.393(5) . ? C3 C4 1.406(5) . ? C4 C24 1.380(5) . ? C4 N5 1.434(4) . ? N5 C6 1.325(4) . ? N5 C23 1.484(4) . ? C6 N7 1.310(4) . ? N7 C8 1.446(4) . ? N7 C21 1.480(4) . ? C8 C13 1.399(4) . ? C8 C9 1.405(4) . ? C9 C10 1.398(5) . ? C9 C18 1.507(5) . ? C10 C11 1.367(5) . ? C11 C12 1.383(5) . ? C12 C13 1.394(5) . ? C13 C14 1.519(4) . ? C14 C17 1.527(6) . ? C14 C15 1.528(5) . ? C18 C20 1.507(5) . ? C18 C19 1.528(5) . ? C21 C22 1.512(4) . ? C22 C23 1.512(5) . ? C24 C25 1.389(5) . ? C25 C26 1.389(5) . ? C26 C27 1.387(5) . ? 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 C3 S2 C28 103.81(18) . . ? C27 C3 C4 117.9(3) . . ? C27 C3 S2 125.7(3) . . ? C4 C3 S2 116.3(3) . . ? C24 C4 C3 121.2(3) . . ? C24 C4 N5 120.2(3) . . ? C3 C4 N5 118.6(3) . . ? C6 N5 C4 120.4(3) . . ? C6 N5 C23 120.0(3) . . ? C4 N5 C23 119.5(2) . . ? N7 C6 N5 123.5(3) . . ? C6 N7 C8 120.4(3) . . ? C6 N7 C21 122.2(3) . . ? C8 N7 C21 117.2(2) . . ? C13 C8 C9 123.2(3) . . ? C13 C8 N7 118.7(3) . . ? C9 C8 N7 118.1(3) . . ? C10 C9 C8 116.5(3) . . ? C10 C9 C18 121.0(3) . . ? C8 C9 C18 122.5(3) . . ? C11 C10 C9 121.5(3) . . ? C10 C11 C12 120.8(3) . . ? C11 C12 C13 120.8(3) . . ? C12 C13 C8 117.1(3) . . ? C12 C13 C14 121.0(3) . . ? C8 C13 C14 121.8(3) . . ? C13 C14 C17 110.5(3) . . ? C13 C14 C15 112.3(3) . . ? C17 C14 C15 110.3(3) . . ? C9 C18 C20 113.7(3) . . ? C9 C18 C19 110.3(3) . . ? C20 C18 C19 110.1(3) . . ? N7 C21 C22 110.4(3) . . ? C21 C22 C23 110.1(3) . . ? N5 C23 C22 109.3(3) . . ? C4 C24 C25 120.4(3) . . ? C26 C25 C24 118.7(3) . . ? C27 C26 C25 121.2(3) . . ? C26 C27 C3 120.5(3) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.54 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.800 _refine_diff_density_min -1.247 _refine_diff_density_rms 0.093 # Attachment 'kjc0814.cif' data_kjc0814 _database_code_depnum_ccdc_archive 'CCDC 733099' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H44 Cl Ir N2 O' _chemical_formula_sum 'C32 H44 Cl Ir N2 O' _chemical_formula_weight 700.34 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 0.0000 0.0000 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.1870(2) _cell_length_b 16.5340(3) _cell_length_c 19.4270(3) _cell_angle_alpha 90.00 _cell_angle_beta 118.7510(10) _cell_angle_gamma 90.00 _cell_volume 2868.73(9) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5197 _cell_measurement_theta_min 3.18 _cell_measurement_theta_max 27.47 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max .38 _exptl_crystal_size_mid .08 _exptl_crystal_size_min .05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.622 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408 _exptl_absorpt_coefficient_mu 4.775 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min .7001 _exptl_absorpt_correction_T_max .8993 _exptl_absorpt_process_details Denzo/Scalepack _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'CCD scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 46665 _diffrn_reflns_av_R_equivalents 0.1803 _diffrn_reflns_av_sigmaI/netI 0.0845 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.18 _diffrn_reflns_theta_max 27.47 _reflns_number_total 6540 _reflns_number_gt 5197 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'cOLLECT,Nonius BV, 1997-2001' _computing_cell_refinement DENZO/SCALEPACK _computing_data_reduction DENZO/SCALEPACK _computing_structure_solution SHELXs-97 _computing_structure_refinement SHELXL-97 _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^)+(0.0542P)^2^+8.4286P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6540 _refine_ls_number_parameters 339 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0712 _refine_ls_R_factor_gt 0.0493 _refine_ls_wR_factor_ref 0.1267 _refine_ls_wR_factor_gt 0.1140 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6903(7) 0.2287(3) 0.3805(3) 0.0180(12) Uani 1 1 d . . . C2 C 0.5169(8) 0.2504(4) 0.4363(4) 0.0262(14) Uani 1 1 d . . . H2A H 0.5965 0.2311 0.4878 0.031 Uiso 1 1 calc R . . H2B H 0.4215 0.2249 0.4265 0.031 Uiso 1 1 calc R . . C3 C 0.5028(7) 0.3421(4) 0.4390(4) 0.0283(15) Uani 1 1 d . . . H3A H 0.4931 0.3571 0.4857 0.034 Uiso 1 1 calc R . . H3B H 0.4116 0.3604 0.3917 0.034 Uiso 1 1 calc R . . C4 C 0.6403(8) 0.3838(4) 0.4428(4) 0.0287(15) Uani 1 1 d . . . H4A H 0.6242 0.3916 0.3888 0.034 Uiso 1 1 calc R . . H4B H 0.6519 0.4378 0.4670 0.034 Uiso 1 1 calc R . . C5 C 0.7827(7) 0.3357(4) 0.4896(3) 0.0226(13) Uani 1 1 d . . . H5A H 0.8696 0.3727 0.5079 0.027 Uiso 1 1 calc R . . H5B H 0.7822 0.3129 0.5366 0.027 Uiso 1 1 calc R . . C6 C 0.4377(8) 0.1807(3) 0.3092(4) 0.0271(15) Uani 1 1 d . . . C7 C 0.4150(7) 0.0995(3) 0.3216(3) 0.0247(14) Uani 1 1 d . . . C8 C 0.3075(7) 0.0539(4) 0.2610(4) 0.0273(14) Uani 1 1 d . . . H8 H 0.2933 -0.0015 0.2685 0.033 Uiso 1 1 calc R . . C9 C 0.2205(8) 0.0912(4) 0.1885(4) 0.0321(16) Uani 1 1 d . . . H9 H 0.1470 0.0603 0.1463 0.038 Uiso 1 1 calc R . . C10 C 0.2387(8) 0.1718(4) 0.1766(4) 0.0313(16) Uani 1 1 d . . . H10 H 0.1787 0.1960 0.1268 0.038 Uiso 1 1 calc R . . C11 C 0.3451(8) 0.2169(4) 0.2380(4) 0.0267(14) Uani 1 1 d . . . H11 H 0.3545 0.2731 0.2312 0.032 Uiso 1 1 calc R . . C12 C 0.4915(9) -0.0148(4) 0.4063(4) 0.0361(18) Uani 1 1 d . . . H12A H 0.3873 -0.0269 0.3919 0.054 Uiso 1 1 calc R . . H12B H 0.5566 -0.0294 0.4614 0.054 Uiso 1 1 calc R . . H12C H 0.5205 -0.0459 0.3728 0.054 Uiso 1 1 calc R . . C13 C 0.9549(7) 0.2418(3) 0.4736(3) 0.0186(12) Uani 1 1 d . . . C14 C 1.0527(7) 0.2834(4) 0.4548(3) 0.0211(13) Uani 1 1 d . . . C15 C 1.2002(8) 0.2550(4) 0.4872(4) 0.0281(14) Uani 1 1 d . . . H15 H 1.2685 0.2821 0.4748 0.034 Uiso 1 1 calc R . . C16 C 1.2484(8) 0.1892(4) 0.5363(4) 0.0301(16) Uani 1 1 d . . . H16 H 1.3479 0.1700 0.5559 0.036 Uiso 1 1 calc R . . C17 C 1.1523(8) 0.1509(4) 0.5571(4) 0.0284(15) Uani 1 1 d . . . H17 H 1.1879 0.1066 0.5926 0.034 Uiso 1 1 calc R . . C18 C 1.0030(7) 0.1760(3) 0.5270(3) 0.0230(13) Uani 1 1 d . . . C19 C 1.0085(7) 0.3595(4) 0.4049(3) 0.0247(13) Uani 1 1 d . . . H19 H 0.9005 0.3711 0.3869 0.030 Uiso 1 1 calc R . . C20 C 1.0303(9) 0.3494(5) 0.3325(4) 0.0374(17) Uani 1 1 d . . . H20A H 1.1367 0.3409 0.3494 0.056 Uiso 1 1 calc R . . H20B H 0.9955 0.3983 0.3000 0.056 Uiso 1 1 calc R . . H20C H 0.9726 0.3027 0.3019 0.056 Uiso 1 1 calc R . . C21 C 1.1035(8) 0.4323(4) 0.4540(4) 0.0319(16) Uani 1 1 d . . . H21A H 1.0904 0.4391 0.5005 0.048 Uiso 1 1 calc R . . H21B H 1.0708 0.4816 0.4221 0.048 Uiso 1 1 calc R . . H21C H 1.2094 0.4224 0.4706 0.048 Uiso 1 1 calc R . . C22 C 0.9032(7) 0.1365(4) 0.5546(3) 0.0254(14) Uani 1 1 d . . . H22 H 0.8040 0.1645 0.5284 0.030 Uiso 1 1 calc R . . C23 C 0.9682(10) 0.1461(4) 0.6437(4) 0.0392(18) Uani 1 1 d . . . H23A H 1.0618 0.1154 0.6709 0.059 Uiso 1 1 calc R . . H23B H 0.8962 0.1256 0.6594 0.059 Uiso 1 1 calc R . . H23C H 0.9881 0.2034 0.6578 0.059 Uiso 1 1 calc R . . C24 C 0.8770(8) 0.0471(4) 0.5333(4) 0.0308(15) Uani 1 1 d . . . H24A H 0.8275 0.0411 0.4760 0.046 Uiso 1 1 calc R . . H24B H 0.8134 0.0240 0.5533 0.046 Uiso 1 1 calc R . . H24C H 0.9733 0.0187 0.5567 0.046 Uiso 1 1 calc R . . C25 C 0.7266(7) 0.0687(3) 0.3016(4) 0.0242(14) Uani 1 1 d . . . H25 H 0.6729 0.0766 0.3298 0.029 Uiso 1 1 calc R . . C26 C 0.8699(7) 0.1040(3) 0.3315(3) 0.0234(13) Uani 1 1 d . . . H26 H 0.9072 0.1330 0.3794 0.028 Uiso 1 1 calc R . . C27 C 0.9691(7) 0.0993(4) 0.2934(3) 0.0256(14) Uani 1 1 d . . . H27A H 1.0099 0.0438 0.2995 0.031 Uiso 1 1 calc R . . H27B H 1.0546 0.1368 0.3207 0.031 Uiso 1 1 calc R . . C28 C 0.8835(8) 0.1210(4) 0.2052(4) 0.0309(15) Uani 1 1 d . . . H28A H 0.9548 0.1445 0.1896 0.037 Uiso 1 1 calc R . . H28B H 0.8420 0.0709 0.1744 0.037 Uiso 1 1 calc R . . C29 C 0.7586(9) 0.1798(4) 0.1855(4) 0.0285(15) Uani 1 1 d . . . H29 H 0.7809 0.2360 0.1895 0.034 Uiso 1 1 calc R . . C30 C 0.6114(8) 0.1566(4) 0.1616(3) 0.0289(15) Uani 1 1 d . . . H30 H 0.5395 0.1983 0.1496 0.035 Uiso 1 1 calc R . . C31 C 0.5572(8) 0.0703(4) 0.1533(4) 0.0281(15) Uani 1 1 d . . . H31A H 0.5575 0.0457 0.1068 0.034 Uiso 1 1 calc R . . H31B H 0.4526 0.0703 0.1437 0.034 Uiso 1 1 calc R . . C32 C 0.6526(8) 0.0179(4) 0.2255(4) 0.0305(15) Uani 1 1 d . . . H32A H 0.7314 -0.0096 0.2182 0.037 Uiso 1 1 calc R . . H32B H 0.5886 -0.0243 0.2304 0.037 Uiso 1 1 calc R . . N1 N 0.5531(6) 0.2252(3) 0.3740(3) 0.0219(11) Uani 1 1 d . . . N2 N 0.8016(6) 0.2679(3) 0.4432(3) 0.0187(10) Uani 1 1 d . . . O1 O 0.5064(5) 0.0698(2) 0.3959(2) 0.0275(10) Uani 1 1 d . . . Ir1 Ir 0.70614(3) 0.195137(12) 0.282541(12) 0.01891(10) Uani 1 1 d . . . Cl1 Cl 0.62997(19) 0.33119(9) 0.24063(9) 0.0283(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.020(3) 0.014(3) 0.014(3) 0.002(2) 0.004(2) 0.002(2) C2 0.030(4) 0.021(3) 0.026(3) 0.000(2) 0.013(3) -0.003(3) C3 0.023(3) 0.024(3) 0.033(3) -0.004(3) 0.009(3) 0.000(3) C4 0.030(4) 0.018(3) 0.030(3) -0.005(3) 0.008(3) -0.002(3) C5 0.025(3) 0.019(3) 0.020(3) -0.006(2) 0.008(3) -0.005(3) C6 0.026(4) 0.017(3) 0.025(3) -0.006(2) 0.001(3) -0.002(2) C7 0.025(3) 0.017(3) 0.024(3) -0.002(2) 0.005(3) 0.001(2) C8 0.027(4) 0.025(3) 0.026(3) -0.002(3) 0.010(3) -0.004(3) C9 0.024(4) 0.039(4) 0.024(3) -0.004(3) 0.003(3) -0.012(3) C10 0.026(4) 0.032(3) 0.020(3) 0.002(3) -0.002(3) 0.000(3) C11 0.019(3) 0.021(3) 0.030(3) 0.008(3) 0.004(3) 0.004(3) C12 0.047(5) 0.021(3) 0.028(3) 0.004(3) 0.008(3) -0.002(3) C13 0.018(3) 0.020(3) 0.012(2) 0.000(2) 0.003(2) 0.003(2) C14 0.022(3) 0.023(3) 0.014(3) -0.004(2) 0.006(2) -0.003(2) C15 0.028(4) 0.022(3) 0.029(3) -0.001(3) 0.010(3) 0.002(3) C16 0.024(4) 0.027(3) 0.028(3) -0.001(3) 0.003(3) 0.007(3) C17 0.030(4) 0.019(3) 0.025(3) 0.002(2) 0.004(3) 0.001(3) C18 0.024(3) 0.018(3) 0.022(3) -0.002(2) 0.007(3) 0.000(2) C19 0.020(3) 0.029(3) 0.020(3) 0.000(2) 0.006(3) -0.004(3) C20 0.036(4) 0.047(4) 0.029(4) 0.000(3) 0.015(3) -0.005(3) C21 0.030(4) 0.023(3) 0.034(4) 0.001(3) 0.009(3) 0.000(3) C22 0.028(4) 0.024(3) 0.022(3) 0.005(2) 0.009(3) 0.005(3) C23 0.055(5) 0.036(4) 0.034(4) 0.002(3) 0.027(4) 0.002(4) C24 0.037(4) 0.028(3) 0.031(3) 0.000(3) 0.019(3) -0.004(3) C25 0.035(4) 0.010(3) 0.024(3) 0.001(2) 0.011(3) 0.009(2) C26 0.025(3) 0.017(3) 0.019(3) 0.001(2) 0.004(3) 0.007(2) C27 0.025(3) 0.027(3) 0.027(3) 0.001(3) 0.015(3) 0.007(3) C28 0.028(4) 0.037(4) 0.029(3) -0.002(3) 0.014(3) 0.002(3) C29 0.038(4) 0.030(3) 0.012(3) 0.002(2) 0.008(3) 0.002(3) C30 0.040(4) 0.025(3) 0.012(3) -0.004(2) 0.005(3) 0.002(3) C31 0.030(4) 0.029(3) 0.021(3) -0.005(3) 0.008(3) -0.003(3) C32 0.042(4) 0.018(3) 0.029(3) -0.009(3) 0.015(3) -0.002(3) N1 0.020(3) 0.017(2) 0.019(2) 0.000(2) 0.002(2) -0.003(2) N2 0.021(3) 0.016(2) 0.015(2) -0.0027(19) 0.005(2) -0.002(2) O1 0.028(3) 0.022(2) 0.020(2) -0.0006(17) 0.0012(19) -0.0015(18) Ir1 0.02182(15) 0.01545(13) 0.01344(13) 0.00067(8) 0.00367(10) 0.00099(9) Cl1 0.0311(9) 0.0193(7) 0.0230(7) 0.0053(6) 0.0039(7) 0.0015(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.343(8) . ? C1 N2 1.364(7) . ? C1 Ir1 2.062(6) . ? C2 N1 1.484(8) . ? C2 C3 1.526(9) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.531(10) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.515(9) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 N2 1.507(8) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C11 1.381(9) . ? C6 C7 1.402(8) . ? C6 N1 1.444(8) . ? C7 O1 1.378(7) . ? C7 C8 1.384(8) . ? C8 C9 1.396(9) . ? C8 H8 0.9500 . ? C9 C10 1.380(10) . ? C9 H9 0.9500 . ? C10 C11 1.382(10) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 O1 1.432(7) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.396(9) . ? C13 C18 1.418(8) . ? C13 N2 1.445(8) . ? C14 C15 1.401(9) . ? C14 C19 1.519(8) . ? C15 C16 1.373(9) . ? C15 H15 0.9500 . ? C16 C17 1.380(10) . ? C16 H16 0.9500 . ? C17 C18 1.403(9) . ? C17 H17 0.9500 . ? C18 C22 1.507(9) . ? C19 C20 1.534(9) . ? C19 C21 1.553(9) . ? C19 H19 1.0000 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 C24 1.524(9) . ? C22 C23 1.536(9) . ? C22 H22 1.0000 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C26 1.412(9) . ? C25 C32 1.546(8) . ? C25 Ir1 2.116(5) . ? C25 H25 0.9500 . ? C26 C27 1.514(9) . ? C26 Ir1 2.106(6) . ? C26 H26 0.9500 . ? C27 C28 1.545(9) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 C29 1.498(10) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 C30 1.394(11) . ? C29 Ir1 2.207(7) . ? C29 H29 0.9500 . ? C30 C31 1.511(9) . ? C30 Ir1 2.162(6) . ? C30 H30 0.9500 . ? C31 C32 1.533(9) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? Ir1 Cl1 2.3911(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 119.0(5) . . ? N1 C1 Ir1 116.2(4) . . ? N2 C1 Ir1 123.5(5) . . ? N1 C2 C3 111.8(5) . . ? N1 C2 H2A 109.3 . . ? C3 C2 H2A 109.3 . . ? N1 C2 H2B 109.3 . . ? C3 C2 H2B 109.3 . . ? H2A C2 H2B 107.9 . . ? C2 C3 C4 110.5(5) . . ? C2 C3 H3A 109.5 . . ? C4 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? C5 C4 C3 112.5(5) . . ? C5 C4 H4A 109.1 . . ? C3 C4 H4A 109.1 . . ? C5 C4 H4B 109.1 . . ? C3 C4 H4B 109.1 . . ? H4A C4 H4B 107.8 . . ? N2 C5 C4 113.1(5) . . ? N2 C5 H5A 109.0 . . ? C4 C5 H5A 109.0 . . ? N2 C5 H5B 109.0 . . ? C4 C5 H5B 109.0 . . ? H5A C5 H5B 107.8 . . ? C11 C6 C7 119.9(6) . . ? C11 C6 N1 122.0(5) . . ? C7 C6 N1 118.1(5) . . ? O1 C7 C8 123.9(5) . . ? O1 C7 C6 115.9(5) . . ? C8 C7 C6 120.2(6) . . ? C7 C8 C9 118.5(6) . . ? C7 C8 H8 120.8 . . ? C9 C8 H8 120.8 . . ? C10 C9 C8 121.6(6) . . ? C10 C9 H9 119.2 . . ? C8 C9 H9 119.2 . . ? C9 C10 C11 119.4(6) . . ? C9 C10 H10 120.3 . . ? C11 C10 H10 120.3 . . ? C6 C11 C10 120.3(6) . . ? C6 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? O1 C12 H12A 109.5 . . ? O1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C18 122.0(6) . . ? C14 C13 N2 120.9(5) . . ? C18 C13 N2 117.0(5) . . ? C13 C14 C15 117.7(6) . . ? C13 C14 C19 123.1(6) . . ? C15 C14 C19 119.2(6) . . ? C16 C15 C14 121.6(7) . . ? C16 C15 H15 119.2 . . ? C14 C15 H15 119.2 . . ? C15 C16 C17 120.0(7) . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C16 C17 C18 121.4(6) . . ? C16 C17 H17 119.3 . . ? C18 C17 H17 119.3 . . ? C17 C18 C13 117.1(6) . . ? C17 C18 C22 120.3(5) . . ? C13 C18 C22 122.5(6) . . ? C14 C19 C20 111.5(6) . . ? C14 C19 C21 110.1(5) . . ? C20 C19 C21 109.0(6) . . ? C14 C19 H19 108.7 . . ? C20 C19 H19 108.7 . . ? C21 C19 H19 108.7 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C18 C22 C24 112.5(5) . . ? C18 C22 C23 110.9(6) . . ? C24 C22 C23 109.3(5) . . ? C18 C22 H22 108.0 . . ? C24 C22 H22 108.0 . . ? C23 C22 H22 108.0 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C26 C25 C32 123.3(6) . . ? C26 C25 Ir1 70.1(3) . . ? C32 C25 Ir1 114.1(4) . . ? C26 C25 H25 118.4 . . ? C32 C25 H25 118.4 . . ? Ir1 C25 H25 86.0 . . ? C25 C26 C27 125.5(5) . . ? C25 C26 Ir1 70.8(3) . . ? C27 C26 Ir1 112.7(4) . . ? C25 C26 H26 117.3 . . ? C27 C26 H26 117.3 . . ? Ir1 C26 H26 86.4 . . ? C26 C27 C28 112.1(5) . . ? C26 C27 H27A 109.2 . . ? C28 C27 H27A 109.2 . . ? C26 C27 H27B 109.2 . . ? C28 C27 H27B 109.2 . . ? H27A C27 H27B 107.9 . . ? C29 C28 C27 113.1(5) . . ? C29 C28 H28A 109.0 . . ? C27 C28 H28A 109.0 . . ? C29 C28 H28B 109.0 . . ? C27 C28 H28B 109.0 . . ? H28A C28 H28B 107.8 . . ? C30 C29 C28 123.5(6) . . ? C30 C29 Ir1 69.6(4) . . ? C28 C29 Ir1 112.4(4) . . ? C30 C29 H29 118.2 . . ? C28 C29 H29 118.2 . . ? Ir1 C29 H29 88.0 . . ? C29 C30 C31 125.1(6) . . ? C29 C30 Ir1 73.2(4) . . ? C31 C30 Ir1 110.1(4) . . ? C29 C30 H30 117.4 . . ? C31 C30 H30 117.4 . . ? Ir1 C30 H30 86.6 . . ? C30 C31 C32 113.4(5) . . ? C30 C31 H31A 108.9 . . ? C32 C31 H31A 108.9 . . ? C30 C31 H31B 108.9 . . ? C32 C31 H31B 108.9 . . ? H31A C31 H31B 107.7 . . ? C31 C32 C25 111.8(5) . . ? C31 C32 H32A 109.3 . . ? C25 C32 H32A 109.3 . . ? C31 C32 H32B 109.3 . . ? C25 C32 H32B 109.3 . . ? H32A C32 H32B 107.9 . . ? C1 N1 C6 118.6(5) . . ? C1 N1 C2 124.5(5) . . ? C6 N1 C2 115.9(6) . . ? C1 N2 C13 119.6(5) . . ? C1 N2 C5 126.7(5) . . ? C13 N2 C5 113.7(4) . . ? C7 O1 C12 115.6(5) . . ? C1 Ir1 C26 100.0(2) . . ? C1 Ir1 C25 98.6(2) . . ? C26 Ir1 C25 39.1(2) . . ? C1 Ir1 C30 152.9(3) . . ? C26 Ir1 C30 97.0(2) . . ? C25 Ir1 C30 81.6(2) . . ? C1 Ir1 C29 167.9(2) . . ? C26 Ir1 C29 80.7(2) . . ? C25 Ir1 C29 89.6(2) . . ? C30 Ir1 C29 37.2(3) . . ? C1 Ir1 Cl1 84.49(15) . . ? C26 Ir1 Cl1 152.15(18) . . ? C25 Ir1 Cl1 167.85(18) . . ? C30 Ir1 Cl1 90.29(17) . . ? C29 Ir1 Cl1 89.38(17) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 3.392 _refine_diff_density_min -4.113 _refine_diff_density_rms 0.230 # Attachment 'kjc0818.cif' data_kjc0818c _database_code_depnum_ccdc_archive 'CCDC 733100' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H27 N2 O, B F4' _chemical_formula_sum 'C21 H27 B F4 N2 O' _chemical_formula_weight 410.26 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 '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 0.0060 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 8.978(1) _cell_length_b 16.022(1) _cell_length_c 14.812(1) _cell_angle_alpha 90.00 _cell_angle_beta 104.31(2) _cell_angle_gamma 90.00 _cell_volume 2064.5 _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3073 _cell_measurement_theta_min 3.51 _cell_measurement_theta_max 27.28 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.320 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9742 _exptl_absorpt_correction_T_max 0.9948 _exptl_absorpt_process_details Denzo/Sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'CCD scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 33214 _diffrn_reflns_av_R_equivalents 0.1960 _diffrn_reflns_av_sigmaI/netI 0.1033 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.51 _diffrn_reflns_theta_max 27.28 _reflns_number_total 4552 _reflns_number_gt 3073 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'cOLLECT,Nonius BV, 1997-2001' _computing_cell_refinement DENZO/SCALEPACK _computing_data_reduction DENZO/SCALEPACK _computing_structure_solution SHELXs-97 _computing_structure_refinement SHELXL-97 _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^)+(0.1707P)^2^+5.6557P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4552 _refine_ls_number_parameters 261 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1727 _refine_ls_R_factor_gt 0.1270 _refine_ls_wR_factor_ref 0.3471 _refine_ls_wR_factor_gt 0.3184 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.079 _refine_ls_shift/su_max 0.0003 _refine_ls_shift/su_mean 0.052 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 0.2474(6) 1.0303(3) 0.7147(3) 0.0261(10) Uani 1 1 d . . . H1 H 0.1657 0.9957 0.6823 0.031 Uiso 1 1 calc R . . C2 C 0.4907(6) 1.0375(3) 0.8335(4) 0.0339(11) Uani 1 1 d . . . H2A H 0.5440 1.0520 0.7845 0.041 Uiso 1 1 calc R . . H2B H 0.5550 0.9962 0.8755 0.041 Uiso 1 1 calc R . . C3 C 0.4765(6) 1.1152(3) 0.8888(4) 0.0371(12) Uani 1 1 d . . . H3A H 0.4515 1.0989 0.9478 0.045 Uiso 1 1 calc R . . H3B H 0.5766 1.1447 0.9047 0.045 Uiso 1 1 calc R . . C4 C 0.3536(7) 1.1741(3) 0.8357(4) 0.0396(13) Uani 1 1 d . . . H4A H 0.3745 1.2309 0.8621 0.048 Uiso 1 1 calc R . . H4B H 0.2526 1.1562 0.8443 0.048 Uiso 1 1 calc R . . C5 C 0.3457(7) 1.1773(3) 0.7316(4) 0.0347(12) Uani 1 1 d . . . H5A H 0.2971 1.2304 0.7056 0.042 Uiso 1 1 calc R . . H5B H 0.4513 1.1762 0.7226 0.042 Uiso 1 1 calc R . . C6 C 0.3131(5) 0.9141(3) 0.8174(3) 0.0256(10) Uani 1 1 d . . . C7 C 0.3770(6) 0.8485(3) 0.7780(3) 0.0279(10) Uani 1 1 d . . . C8 C 0.3579(6) 0.7681(3) 0.8105(3) 0.0324(11) Uani 1 1 d . . . H8 H 0.3971 0.7220 0.7832 0.039 Uiso 1 1 calc R . . C9 C 0.2844(6) 0.7530(3) 0.8803(3) 0.0308(11) Uani 1 1 d . . . C10 C 0.2214(6) 0.8205(3) 0.9165(3) 0.0298(11) Uani 1 1 d . . . H10 H 0.1677 0.8107 0.9633 0.036 Uiso 1 1 calc R . . C11 C 0.2340(5) 0.9023(3) 0.8866(3) 0.0264(10) Uani 1 1 d . . . C12 C 0.4613(7) 0.8625(3) 0.7039(4) 0.0397(13) Uani 1 1 d . . . H12A H 0.3932 0.8904 0.6505 0.060 Uiso 1 1 calc R . . H12B H 0.4944 0.8088 0.6840 0.060 Uiso 1 1 calc R . . H12C H 0.5516 0.8977 0.7286 0.060 Uiso 1 1 calc R . . C13 C 0.2753(7) 0.6662(3) 0.9187(4) 0.0415(13) Uani 1 1 d . . . H13A H 0.2917 0.6248 0.8734 0.062 Uiso 1 1 calc R . . H13B H 0.1737 0.6577 0.9305 0.062 Uiso 1 1 calc R . . H13C H 0.3546 0.6597 0.9770 0.062 Uiso 1 1 calc R . . C14 C 0.1676(7) 0.9738(3) 0.9300(4) 0.0359(12) Uani 1 1 d . . . H14A H 0.1098 0.9518 0.9730 0.054 Uiso 1 1 calc R . . H14B H 0.0987 1.0064 0.8811 0.054 Uiso 1 1 calc R . . H14C H 0.2511 1.0096 0.9643 0.054 Uiso 1 1 calc R . . C15 C 0.1633(6) 1.1219(3) 0.5871(3) 0.0281(11) Uani 1 1 d . . . C16 C 0.1872(6) 1.0735(3) 0.5131(3) 0.0303(11) Uani 1 1 d . . . C17 C 0.1007(6) 1.0908(3) 0.4227(3) 0.0366(12) Uani 1 1 d . . . H17 H 0.1159 1.0590 0.3716 0.044 Uiso 1 1 calc R . . C18 C -0.0073(7) 1.1544(3) 0.4082(4) 0.0404(13) Uani 1 1 d . . . H18 H -0.0661 1.1659 0.3468 0.048 Uiso 1 1 calc R . . C19 C -0.0310(7) 1.2016(4) 0.4818(4) 0.0428(14) Uani 1 1 d . . . H19 H -0.1056 1.2449 0.4713 0.051 Uiso 1 1 calc R . . C20 C 0.0562(6) 1.1846(3) 0.5713(4) 0.0354(12) Uani 1 1 d . . . H20 H 0.0415 1.2169 0.6222 0.042 Uiso 1 1 calc R . . C21 C 0.3135(7) 0.9592(4) 0.4606(4) 0.0431(14) Uani 1 1 d . . . H21A H 0.2141 0.9346 0.4296 0.065 Uiso 1 1 calc R . . H21B H 0.3866 0.9146 0.4860 0.065 Uiso 1 1 calc R . . H21C H 0.3526 0.9918 0.4154 0.065 Uiso 1 1 calc R . . N1 N 0.2565(5) 1.1063(2) 0.6801(3) 0.0268(9) Uani 1 1 d . . . N2 N 0.3402(4) 0.9988(2) 0.7890(3) 0.0246(9) Uani 1 1 d . . . O1 O 0.2951(4) 1.0127(2) 0.5350(2) 0.0364(9) Uani 1 1 d . . . F1 F 0.0283(4) 0.8848(3) 0.2505(3) 0.0723(13) Uani 1 1 d . . . F2 F 0.1403(5) 0.8873(2) 0.1300(2) 0.0587(11) Uani 1 1 d . . . F3 F 0.1807(5) 0.9944(2) 0.2329(3) 0.0620(11) Uani 1 1 d . . . F4 F 0.2838(4) 0.8670(2) 0.2781(2) 0.0437(8) Uani 1 1 d D . . B1 B 0.1472(4) 0.9096(2) 0.2222(2) 0.0400(7) 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 0.032(2) 0.028(2) 0.020(2) -0.0010(18) 0.0105(19) 0.0012(19) C2 0.029(3) 0.035(3) 0.036(3) 0.003(2) 0.005(2) -0.003(2) C3 0.045(3) 0.038(3) 0.026(3) -0.002(2) 0.003(2) -0.009(2) C4 0.055(3) 0.031(3) 0.032(3) -0.009(2) 0.010(2) -0.008(2) C5 0.050(3) 0.023(2) 0.032(3) -0.002(2) 0.011(2) -0.004(2) C6 0.027(2) 0.027(2) 0.020(2) 0.0038(18) 0.0022(18) 0.0017(19) C7 0.034(3) 0.029(2) 0.019(2) 0.0012(18) 0.0039(19) 0.003(2) C8 0.044(3) 0.026(2) 0.025(2) 0.0020(19) 0.004(2) 0.004(2) C9 0.034(3) 0.025(2) 0.028(2) 0.0037(19) -0.003(2) -0.007(2) C10 0.030(2) 0.033(3) 0.026(2) 0.008(2) 0.0044(19) 0.000(2) C11 0.028(2) 0.027(2) 0.024(2) 0.0005(18) 0.0045(18) -0.0041(19) C12 0.055(3) 0.037(3) 0.032(3) 0.003(2) 0.022(2) 0.010(3) C13 0.051(3) 0.031(3) 0.040(3) 0.007(2) 0.006(3) -0.005(2) C14 0.048(3) 0.033(3) 0.034(3) 0.001(2) 0.022(2) 0.004(2) C15 0.035(3) 0.028(2) 0.023(2) 0.0045(18) 0.0095(19) -0.003(2) C16 0.037(3) 0.032(3) 0.023(2) 0.0055(19) 0.009(2) -0.001(2) C17 0.044(3) 0.040(3) 0.023(2) 0.002(2) 0.004(2) -0.010(2) C18 0.048(3) 0.038(3) 0.029(3) 0.011(2) -0.003(2) -0.005(2) C19 0.048(3) 0.038(3) 0.042(3) 0.015(2) 0.011(3) 0.008(2) C20 0.045(3) 0.027(3) 0.037(3) 0.007(2) 0.015(2) 0.007(2) C21 0.059(4) 0.046(3) 0.025(3) -0.006(2) 0.013(2) 0.005(3) N1 0.036(2) 0.028(2) 0.0172(18) 0.0025(15) 0.0074(16) 0.0003(17) N2 0.030(2) 0.025(2) 0.0192(18) 0.0007(15) 0.0075(15) -0.0035(16) O1 0.044(2) 0.042(2) 0.0228(17) -0.0050(15) 0.0075(15) 0.0083(16) F1 0.048(2) 0.108(3) 0.067(3) 0.037(2) 0.0239(19) 0.011(2) F2 0.092(3) 0.058(2) 0.0286(18) -0.0022(15) 0.0189(18) 0.012(2) F3 0.090(3) 0.039(2) 0.050(2) -0.0014(16) 0.002(2) 0.0064(18) F4 0.0427(18) 0.0449(19) 0.0435(19) 0.0075(14) 0.0103(14) 0.0030(14) _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 N2 1.307(6) . ? C1 N1 1.330(6) . ? C2 N2 1.485(6) . ? C2 C3 1.514(8) . ? C3 C4 1.515(8) . ? C4 C5 1.526(7) . ? C5 N1 1.489(6) . ? C6 C7 1.393(7) . ? C6 C11 1.397(6) . ? C6 N2 1.459(6) . ? C7 C8 1.400(7) . ? C7 C12 1.497(7) . ? C8 C9 1.378(7) . ? C9 C10 1.388(7) . ? C9 C13 1.513(7) . ? C10 C11 1.397(7) . ? C11 C14 1.506(7) . ? C15 C20 1.370(7) . ? C15 C16 1.402(7) . ? C15 N1 1.446(6) . ? C16 O1 1.355(6) . ? C16 C17 1.399(7) . ? C17 C18 1.387(8) . ? C18 C19 1.385(8) . ? C19 C20 1.389(8) . ? C21 O1 1.438(6) . ? F1 B1 1.302(5) . ? F2 B1 1.399(5) . ? F3 B1 1.392(5) . ? F4 B1 1.467(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C1 N1 126.2(5) . . ? N2 C2 C3 113.3(4) . . ? C4 C3 C2 112.3(4) . . ? C3 C4 C5 113.1(5) . . ? N1 C5 C4 112.1(4) . . ? C7 C6 C11 122.8(4) . . ? C7 C6 N2 117.8(4) . . ? C11 C6 N2 119.2(4) . . ? C6 C7 C8 116.9(4) . . ? C6 C7 C12 121.9(4) . . ? C8 C7 C12 121.2(4) . . ? C9 C8 C7 122.7(5) . . ? C8 C9 C10 118.0(4) . . ? C8 C9 C13 121.5(5) . . ? C10 C9 C13 120.4(5) . . ? C9 C10 C11 122.4(4) . . ? C6 C11 C10 117.0(4) . . ? C6 C11 C14 122.5(4) . . ? C10 C11 C14 120.4(4) . . ? C20 C15 C16 120.6(5) . . ? C20 C15 N1 120.4(4) . . ? C16 C15 N1 119.0(4) . . ? O1 C16 C17 124.5(5) . . ? O1 C16 C15 116.7(4) . . ? C17 C16 C15 118.8(5) . . ? C18 C17 C16 119.7(5) . . ? C17 C18 C19 121.1(5) . . ? C20 C19 C18 118.9(5) . . ? C15 C20 C19 120.9(5) . . ? C1 N1 C15 116.7(4) . . ? C1 N1 C5 125.3(4) . . ? C15 N1 C5 117.9(4) . . ? C1 N2 C6 119.0(4) . . ? C1 N2 C2 122.2(4) . . ? C6 N2 C2 117.3(4) . . ? C16 O1 C21 117.2(4) . . ? F1 B1 F3 115.7(4) . . ? F1 B1 F2 113.2(4) . . ? F3 B1 F2 108.4(3) . . ? F1 B1 F4 108.3(3) . . ? F3 B1 F4 105.2(3) . . ? F2 B1 F4 105.2(3) . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 27.28 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 1.537 _refine_diff_density_min -0.460 _refine_diff_density_rms 0.104 # Attachment 'kjc0819.cif' data_kjc0819 _database_code_depnum_ccdc_archive 'CCDC 733101' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H25 N2 S, B F4' _chemical_formula_sum 'C20 H25 B F4 N2 S' _chemical_formula_weight 412.29 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 0.0000 0.0000 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.0040(2) _cell_length_b 16.1800(4) _cell_length_c 16.1990(5) _cell_angle_alpha 90.00 _cell_angle_beta 102.2990(10) _cell_angle_gamma 90.00 _cell_volume 2049.70(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3473 _cell_measurement_theta_min 3.48 _cell_measurement_theta_max 27.49 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max .50 _exptl_crystal_size_mid .38 _exptl_crystal_size_min .08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.201 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min .8123 _exptl_absorpt_correction_T_max .9025 _exptl_absorpt_process_details Denzo/Scalepack _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'CCD scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20675 _diffrn_reflns_av_R_equivalents 0.1194 _diffrn_reflns_av_sigmaI/netI 0.0752 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 3.48 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4659 _reflns_number_gt 3473 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'cOLLECT,Nonius BV, 1997-2001' _computing_cell_refinement DENZO/SCALEPACK _computing_data_reduction DENZO/SCALEPACK _computing_structure_solution SHELXs-97 _computing_structure_refinement SHELXL-97 _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^)+(0.0480P)^2^+1.0772P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4659 _refine_ls_number_parameters 257 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0846 _refine_ls_R_factor_gt 0.0563 _refine_ls_wR_factor_ref 0.1412 _refine_ls_wR_factor_gt 0.1273 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.0639(2) 0.03015(12) 0.25067(13) 0.0246(4) Uani 1 1 d . . . H1 H 0.0790 -0.0191 0.2236 0.030 Uiso 1 1 calc R . . C2 C -0.0228(4) 0.10174(13) 0.36700(15) 0.0417(6) Uani 1 1 d . . . H2A H -0.0058 0.0885 0.4266 0.050 Uiso 1 1 calc R . . H2B H -0.1378 0.1232 0.3483 0.050 Uiso 1 1 calc R . . C3 C 0.1057(3) 0.16606(13) 0.35381(15) 0.0387(5) Uani 1 1 d . . . H3A H 0.2200 0.1480 0.3805 0.046 Uiso 1 1 calc R . . H3B H 0.0831 0.2177 0.3799 0.046 Uiso 1 1 calc R . . C4 C 0.0950(3) 0.17952(12) 0.26045(14) 0.0340(5) Uani 1 1 d . . . H4A H -0.0130 0.2056 0.2353 0.041 Uiso 1 1 calc R . . H4B H 0.1868 0.2157 0.2524 0.041 Uiso 1 1 calc R . . C5 C -0.0529(3) -0.05118(12) 0.34909(13) 0.0270(4) Uani 1 1 d . . . C6 C 0.0672(3) -0.09805(12) 0.40550(13) 0.0263(4) Uani 1 1 d . . . C7 C 0.0122(3) -0.17085(12) 0.43681(13) 0.0282(4) Uani 1 1 d . . . H7 H 0.0897 -0.2039 0.4734 0.034 Uiso 1 1 calc R . . C8 C -0.1585(3) -0.19429(13) 0.41344(13) 0.0303(5) Uani 1 1 d . . . H8 H -0.1945 -0.2422 0.4361 0.036 Uiso 1 1 calc R . . C9 C -0.2756(3) -0.14798(13) 0.35730(14) 0.0334(5) Uani 1 1 d . . . H9 H -0.3891 -0.1646 0.3414 0.040 Uiso 1 1 calc R . . C10 C -0.2200(3) -0.07630(13) 0.32530(14) 0.0312(5) Uani 1 1 d . . . H10 H -0.2971 -0.0446 0.2871 0.037 Uiso 1 1 calc R . . C11 C 0.3967(3) -0.14441(18) 0.48729(19) 0.0524(7) Uani 1 1 d . . . H11A H 0.3571 -0.1566 0.5379 0.079 Uiso 1 1 calc R . . H11B H 0.5160 -0.1305 0.5017 0.079 Uiso 1 1 calc R . . H11C H 0.3805 -0.1919 0.4510 0.079 Uiso 1 1 calc R . . C12 C 0.1682(2) 0.09866(11) 0.14058(13) 0.0226(4) Uani 1 1 d . . . C13 C 0.0480(2) 0.10182(11) 0.06474(13) 0.0233(4) Uani 1 1 d . . . C14 C 0.1080(2) 0.10686(12) -0.00972(13) 0.0266(4) Uani 1 1 d . . . H14 H 0.0297 0.1084 -0.0611 0.032 Uiso 1 1 calc R . . C15 C 0.2821(3) 0.10965(12) -0.00928(14) 0.0291(5) Uani 1 1 d . . . C16 C 0.3968(2) 0.10592(13) 0.06826(15) 0.0321(5) Uani 1 1 d . . . H16 H 0.5134 0.1073 0.0692 0.039 Uiso 1 1 calc R . . C17 C 0.3441(2) 0.10031(12) 0.14395(14) 0.0281(5) Uani 1 1 d . . . C18 C -0.1415(2) 0.10362(14) 0.06248(14) 0.0311(5) Uani 1 1 d . . . H18A H -0.2035 0.1071 0.0049 0.047 Uiso 1 1 calc R . . H18B H -0.1678 0.1508 0.0933 0.047 Uiso 1 1 calc R . . H18C H -0.1737 0.0541 0.0877 0.047 Uiso 1 1 calc R . . C19 C 0.3448(3) 0.11670(16) -0.09048(17) 0.0445(6) Uani 1 1 d . . . H19A H 0.4198 0.1634 -0.0873 0.067 Uiso 1 1 calc R . . H19B H 0.2490 0.1238 -0.1369 0.067 Uiso 1 1 calc R . . H19C H 0.4055 0.0673 -0.0989 0.067 Uiso 1 1 calc R . . C20 C 0.4710(3) 0.09678(16) 0.22773(16) 0.0429(6) Uani 1 1 d . . . H20A H 0.5849 0.0930 0.2179 0.064 Uiso 1 1 calc R . . H20B H 0.4477 0.0492 0.2588 0.064 Uiso 1 1 calc R . . H20C H 0.4608 0.1459 0.2596 0.064 Uiso 1 1 calc R . . N1 N -0.0018(2) 0.02653(10) 0.31872(11) 0.0296(4) Uani 1 1 d . . . N2 N 0.1088(2) 0.09896(10) 0.21918(11) 0.0254(4) Uani 1 1 d . . . S1 S 0.27792(7) -0.05886(4) 0.43378(4) 0.04098(18) Uani 1 1 d . . . B1 B 0.2621(3) -0.18202(15) 0.20788(17) 0.0330(6) Uani 1 1 d . . . F2 F 0.2663(2) -0.22849(10) 0.13658(11) 0.0597(4) Uani 1 1 d . . . F3 F 0.36342(19) -0.11270(9) 0.21119(10) 0.0538(4) Uani 1 1 d . . . F4 F 0.09313(15) -0.15665(7) 0.20449(8) 0.0375(3) Uani 1 1 d . . . F5 F 0.31434(18) -0.23015(9) 0.27949(10) 0.0534(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0294(10) 0.0206(9) 0.0236(10) -0.0003(8) 0.0051(8) 0.0023(8) C2 0.0757(17) 0.0245(11) 0.0303(12) -0.0036(10) 0.0236(12) 0.0000(11) C3 0.0663(15) 0.0225(10) 0.0273(12) -0.0039(9) 0.0097(11) -0.0019(10) C4 0.0557(13) 0.0177(10) 0.0310(12) -0.0013(9) 0.0147(10) 0.0010(9) C5 0.0389(11) 0.0210(9) 0.0229(10) -0.0013(8) 0.0108(9) 0.0007(8) C6 0.0320(10) 0.0254(10) 0.0226(10) -0.0029(8) 0.0085(8) -0.0023(8) C7 0.0385(11) 0.0221(10) 0.0235(10) 0.0004(8) 0.0057(9) 0.0022(8) C8 0.0411(11) 0.0235(10) 0.0291(11) -0.0023(9) 0.0136(9) -0.0046(9) C9 0.0315(11) 0.0338(11) 0.0362(13) -0.0053(10) 0.0100(9) -0.0021(9) C10 0.0358(11) 0.0308(11) 0.0277(11) -0.0002(9) 0.0082(9) 0.0056(9) C11 0.0343(12) 0.0704(18) 0.0502(16) 0.0152(14) 0.0037(11) 0.0034(12) C12 0.0256(9) 0.0167(9) 0.0268(10) 0.0006(8) 0.0086(8) 0.0022(7) C13 0.0218(9) 0.0209(9) 0.0282(11) -0.0001(8) 0.0078(8) -0.0004(7) C14 0.0297(10) 0.0259(10) 0.0251(11) -0.0030(9) 0.0078(8) -0.0008(8) C15 0.0336(10) 0.0220(10) 0.0366(12) -0.0018(9) 0.0185(9) 0.0006(8) C16 0.0205(9) 0.0274(10) 0.0512(14) 0.0051(10) 0.0140(9) 0.0026(8) C17 0.0248(9) 0.0192(9) 0.0386(12) 0.0039(9) 0.0034(9) 0.0016(8) C18 0.0220(9) 0.0360(11) 0.0354(12) -0.0007(10) 0.0066(8) -0.0015(8) C19 0.0486(13) 0.0447(14) 0.0495(15) -0.0017(12) 0.0314(12) -0.0008(11) C20 0.0305(11) 0.0431(13) 0.0488(15) 0.0123(12) -0.0057(10) 0.0008(10) N1 0.0467(10) 0.0188(8) 0.0255(9) 0.0001(7) 0.0129(8) -0.0006(7) N2 0.0327(9) 0.0197(8) 0.0247(9) 0.0002(7) 0.0080(7) 0.0015(7) S1 0.0363(3) 0.0408(3) 0.0427(4) 0.0041(3) 0.0012(3) -0.0097(2) B1 0.0371(13) 0.0266(12) 0.0362(14) -0.0036(11) 0.0098(11) 0.0006(10) F2 0.0707(10) 0.0542(9) 0.0605(10) -0.0227(8) 0.0278(8) 0.0018(8) F3 0.0539(9) 0.0453(8) 0.0667(11) -0.0049(8) 0.0230(8) -0.0161(7) F4 0.0352(7) 0.0321(7) 0.0444(8) -0.0009(6) 0.0068(6) 0.0047(5) F5 0.0504(8) 0.0475(8) 0.0571(10) 0.0152(7) -0.0001(7) 0.0097(7) _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 N2 1.307(3) . ? C1 N1 1.320(3) . ? C1 H1 0.9300 . ? C2 N1 1.475(3) . ? C2 C3 1.510(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.512(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 N2 1.480(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C10 1.372(3) . ? C5 C6 1.400(3) . ? C5 N1 1.441(3) . ? C6 C7 1.391(3) . ? C6 S1 1.768(2) . ? C7 C8 1.391(3) . ? C7 H7 0.9300 . ? C8 C9 1.380(3) . ? C8 H8 0.9300 . ? C9 C10 1.382(3) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 S1 1.794(3) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.391(3) . ? C12 C17 1.398(3) . ? C12 N2 1.451(3) . ? C13 C14 1.393(3) . ? C13 C18 1.509(3) . ? C14 C15 1.392(3) . ? C14 H14 0.9300 . ? C15 C16 1.391(3) . ? C15 C19 1.509(3) . ? C16 C17 1.382(3) . ? C16 H16 0.9300 . ? C17 C20 1.513(3) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? B1 F3 1.379(3) . ? B1 F2 1.385(3) . ? B1 F5 1.386(3) . ? B1 F4 1.403(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C1 N1 123.76(18) . . ? N2 C1 H1 118.1 . . ? N1 C1 H1 118.1 . . ? N1 C2 C3 109.61(19) . . ? N1 C2 H2A 109.7 . . ? C3 C2 H2A 109.7 . . ? N1 C2 H2B 109.7 . . ? C3 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? C2 C3 C4 110.22(19) . . ? C2 C3 H3A 109.6 . . ? C4 C3 H3A 109.6 . . ? C2 C3 H3B 109.6 . . ? C4 C3 H3B 109.6 . . ? H3A C3 H3B 108.1 . . ? N2 C4 C3 109.34(16) . . ? N2 C4 H4A 109.8 . . ? C3 C4 H4A 109.8 . . ? N2 C4 H4B 109.8 . . ? C3 C4 H4B 109.8 . . ? H4A C4 H4B 108.3 . . ? C10 C5 C6 121.05(19) . . ? C10 C5 N1 119.54(18) . . ? C6 C5 N1 119.34(18) . . ? C7 C6 C5 118.03(18) . . ? C7 C6 S1 124.60(16) . . ? C5 C6 S1 117.35(15) . . ? C8 C7 C6 120.06(19) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C9 C8 C7 121.4(2) . . ? C9 C8 H8 119.3 . . ? C7 C8 H8 119.3 . . ? C8 C9 C10 118.4(2) . . ? C8 C9 H9 120.8 . . ? C10 C9 H9 120.8 . . ? C5 C10 C9 121.0(2) . . ? C5 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? S1 C11 H11A 109.5 . . ? S1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? S1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 C17 122.38(19) . . ? C13 C12 N2 118.73(16) . . ? C17 C12 N2 118.77(18) . . ? C12 C13 C14 117.75(17) . . ? C12 C13 C18 121.65(18) . . ? C14 C13 C18 120.55(18) . . ? C15 C14 C13 121.81(19) . . ? C15 C14 H14 119.1 . . ? C13 C14 H14 119.1 . . ? C16 C15 C14 118.10(19) . . ? C16 C15 C19 120.82(19) . . ? C14 C15 C19 121.1(2) . . ? C17 C16 C15 122.44(18) . . ? C17 C16 H16 118.8 . . ? C15 C16 H16 118.8 . . ? C16 C17 C12 117.51(19) . . ? C16 C17 C20 121.67(19) . . ? C12 C17 C20 120.8(2) . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C15 C19 H19A 109.5 . . ? C15 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C15 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C1 N1 C5 121.09(17) . . ? C1 N1 C2 121.11(17) . . ? C5 N1 C2 117.79(17) . . ? C1 N2 C12 120.58(16) . . ? C1 N2 C4 121.39(17) . . ? C12 N2 C4 118.00(15) . . ? C6 S1 C11 103.08(11) . . ? F3 B1 F2 110.8(2) . . ? F3 B1 F5 110.76(19) . . ? F2 B1 F5 109.66(19) . . ? F3 B1 F4 108.53(18) . . ? F2 B1 F4 108.71(19) . . ? F5 B1 F4 108.3(2) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.257 _refine_diff_density_min -0.432 _refine_diff_density_rms 0.056 # Attachment 'kjc0827.cif' data_kjc0827 _database_code_depnum_ccdc_archive 'CCDC 733102' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C32 H44 Cl N2 O Rh' _chemical_formula_sum 'C32 H44 Cl N2 O Rh' _chemical_formula_weight 611.05 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 0.0000 0.0000 '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 0.0060 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.1760(2) _cell_length_b 16.5830(3) _cell_length_c 17.0760(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.8630(10) _cell_angle_gamma 90.00 _cell_volume 2877.95(10) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5110 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 27.47 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.410 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1280 _exptl_absorpt_coefficient_mu 0.714 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.8530 _exptl_absorpt_correction_T_max 0.9321 _exptl_absorpt_process_details Denzo/Scalepack _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'CCD scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11968 _diffrn_reflns_av_R_equivalents 0.0408 _diffrn_reflns_av_sigmaI/netI 0.0622 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.59 _diffrn_reflns_theta_max 27.47 _reflns_number_total 6546 _reflns_number_gt 5110 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'cOLLECT,Nonius BV, 1997-2001' _computing_cell_refinement DENZO/SCALEPACK _computing_data_reduction DENZO/SCALEPACK _computing_structure_solution SHELXs-97 _computing_structure_refinement SHELXL-97 _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^)+(0.0583P)^2^+5.8909P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6546 _refine_ls_number_parameters 339 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0680 _refine_ls_R_factor_gt 0.0484 _refine_ls_wR_factor_ref 0.1301 _refine_ls_wR_factor_gt 0.1198 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6891(4) 0.2278(2) 0.3816(2) 0.0172(7) Uani 1 1 d . . . C2 C 0.9205(4) 0.2512(2) 0.4361(2) 0.0255(8) Uani 1 1 d . . . H2A H 1.0063 0.2263 0.4254 0.031 Uiso 1 1 calc R . . H2B H 0.8945 0.2318 0.4879 0.031 Uiso 1 1 calc R . . C3 C 0.9357(4) 0.3418(2) 0.4385(3) 0.0303(9) Uani 1 1 d . . . H3A H 0.9781 0.3603 0.3908 0.036 Uiso 1 1 calc R . . H3B H 0.9932 0.3571 0.4846 0.036 Uiso 1 1 calc R . . C4 C 0.8016(4) 0.3829(2) 0.4435(2) 0.0256(9) Uani 1 1 d . . . H4A H 0.8143 0.4366 0.4681 0.031 Uiso 1 1 calc R . . H4B H 0.7627 0.3912 0.3898 0.031 Uiso 1 1 calc R . . C5 C 0.7070(4) 0.3348(2) 0.4901(2) 0.0221(8) Uani 1 1 d . . . H5A H 0.7550 0.3121 0.5369 0.026 Uiso 1 1 calc R . . H5B H 0.6381 0.3713 0.5085 0.026 Uiso 1 1 calc R . . C6 C 0.8718(4) 0.1811(2) 0.3099(2) 0.0224(8) Uani 1 1 d . . . C7 C 0.9072(4) 0.0996(2) 0.3223(2) 0.0245(8) Uani 1 1 d . . . C8 C 0.9539(4) 0.0549(2) 0.2611(2) 0.0280(9) Uani 1 1 d . . . H8 H 0.9750 -0.0005 0.2681 0.034 Uiso 1 1 calc R . . C9 C 0.9696(4) 0.0922(3) 0.1891(2) 0.0311(9) Uani 1 1 d . . . H9 H 1.0012 0.0615 0.1469 0.037 Uiso 1 1 calc R . . C10 C 0.9405(4) 0.1723(3) 0.1776(2) 0.0305(9) Uani 1 1 d . . . H10 H 0.9539 0.1970 0.1285 0.037 Uiso 1 1 calc R . . C11 C 0.8906(4) 0.2176(2) 0.2392(2) 0.0259(9) Uani 1 1 d . . . H11 H 0.8700 0.2730 0.2318 0.031 Uiso 1 1 calc R . . C12 C 0.9146(5) -0.0141(3) 0.4065(3) 0.0365(11) Uani 1 1 d . . . H12A H 0.8550 -0.0448 0.3708 0.055 Uiso 1 1 calc R . . H12B H 0.8994 -0.0291 0.4608 0.055 Uiso 1 1 calc R . . H12C H 1.0059 -0.0262 0.3950 0.055 Uiso 1 1 calc R . . C13 C 0.5195(4) 0.2409(2) 0.4744(2) 0.0190(7) Uani 1 1 d . . . C14 C 0.5240(4) 0.1758(2) 0.5275(2) 0.0204(8) Uani 1 1 d . . . C15 C 0.4064(4) 0.1502(2) 0.5576(2) 0.0262(9) Uani 1 1 d . . . H15 H 0.4071 0.1056 0.5926 0.031 Uiso 1 1 calc R . . C16 C 0.2886(4) 0.1882(2) 0.5376(3) 0.0282(9) Uani 1 1 d . . . H16 H 0.2090 0.1691 0.5577 0.034 Uiso 1 1 calc R . . C17 C 0.2873(4) 0.2543(2) 0.4881(2) 0.0279(9) Uani 1 1 d . . . H17 H 0.2062 0.2807 0.4753 0.033 Uiso 1 1 calc R . . C18 C 0.4024(4) 0.2831(2) 0.4563(2) 0.0233(8) Uani 1 1 d . . . C19 C 0.6521(4) 0.1354(2) 0.5555(2) 0.0243(8) Uani 1 1 d . . . H19 H 0.7251 0.1629 0.5289 0.029 Uiso 1 1 calc R . . C20 C 0.6567(4) 0.0466(2) 0.5339(3) 0.0307(9) Uani 1 1 d . . . H20A H 0.5833 0.0183 0.5568 0.046 Uiso 1 1 calc R . . H20B H 0.7401 0.0232 0.5542 0.046 Uiso 1 1 calc R . . H20C H 0.6496 0.0409 0.4767 0.046 Uiso 1 1 calc R . . C21 C 0.6784(5) 0.1456(3) 0.6433(3) 0.0386(11) Uani 1 1 d . . . H21A H 0.6781 0.2031 0.6565 0.058 Uiso 1 1 calc R . . H21B H 0.7643 0.1224 0.6589 0.058 Uiso 1 1 calc R . . H21C H 0.6096 0.1179 0.6713 0.058 Uiso 1 1 calc R . . C22 C 0.3953(4) 0.3584(2) 0.4061(2) 0.0251(8) Uani 1 1 d . . . H22 H 0.4854 0.3702 0.3882 0.030 Uiso 1 1 calc R . . C23 C 0.3501(5) 0.4306(2) 0.4546(3) 0.0321(10) Uani 1 1 d . . . H23A H 0.2621 0.4198 0.4730 0.048 Uiso 1 1 calc R . . H23B H 0.3476 0.4792 0.4220 0.048 Uiso 1 1 calc R . . H23C H 0.4118 0.4387 0.4999 0.048 Uiso 1 1 calc R . . C24 C 0.3024(5) 0.3480(3) 0.3339(3) 0.0375(11) Uani 1 1 d . . . H24A H 0.3279 0.3000 0.3048 0.056 Uiso 1 1 calc R . . H24B H 0.3075 0.3956 0.3003 0.056 Uiso 1 1 calc R . . H24C H 0.2120 0.3416 0.3503 0.056 Uiso 1 1 calc R . . C25 C 0.4644(4) 0.1035(2) 0.3319(2) 0.0239(8) Uani 1 1 d . . . H25 H 0.4757 0.1313 0.3804 0.029 Uiso 1 1 calc R . . C26 C 0.5759(4) 0.0678(2) 0.3019(2) 0.0234(8) Uani 1 1 d . . . H26 H 0.6578 0.0749 0.3303 0.028 Uiso 1 1 calc R . . C27 C 0.5744(5) 0.0184(2) 0.2266(2) 0.0314(9) Uani 1 1 d . . . H27A H 0.4880 -0.0086 0.2187 0.038 Uiso 1 1 calc R . . H27B H 0.6428 -0.0240 0.2318 0.038 Uiso 1 1 calc R . . C28 C 0.5995(5) 0.0709(3) 0.1545(2) 0.0334(10) Uani 1 1 d . . . H28A H 0.6951 0.0712 0.1462 0.040 Uiso 1 1 calc R . . H28B H 0.5548 0.0459 0.1077 0.040 Uiso 1 1 calc R . . C29 C 0.5528(4) 0.1570(2) 0.1610(2) 0.0276(9) Uani 1 1 d . . . H29 H 0.6121 0.1986 0.1479 0.033 Uiso 1 1 calc R . . C30 C 0.4299(4) 0.1799(3) 0.1846(2) 0.0278(9) Uani 1 1 d . . . H30 H 0.4113 0.2359 0.1884 0.033 Uiso 1 1 calc R . . C31 C 0.3239(4) 0.1206(3) 0.2047(2) 0.0320(10) Uani 1 1 d . . . H31A H 0.3357 0.0700 0.1751 0.038 Uiso 1 1 calc R . . H31B H 0.2368 0.1432 0.1884 0.038 Uiso 1 1 calc R . . C32 C 0.3272(4) 0.1015(3) 0.2932(2) 0.0300(9) Uani 1 1 d . . . H32A H 0.2714 0.1410 0.3196 0.036 Uiso 1 1 calc R . . H32B H 0.2889 0.0473 0.3007 0.036 Uiso 1 1 calc R . . N1 N 0.6429(3) 0.26765(17) 0.44403(17) 0.0181(6) Uani 1 1 d . . . N2 N 0.8205(3) 0.22495(19) 0.37495(18) 0.0216(7) Uani 1 1 d . . . O1 O 0.8905(3) 0.07014(16) 0.39602(16) 0.0291(7) Uani 1 1 d . . . Rh1 Rh 0.57844(3) 0.194751(17) 0.282996(16) 0.01874(10) Uani 1 1 d . . . Cl1 Cl 0.60924(9) 0.33519(5) 0.24075(5) 0.01671(18) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.019(2) 0.0170(16) 0.0155(16) 0.0041(13) 0.0029(14) -0.0020(14) C2 0.016(2) 0.033(2) 0.028(2) -0.0034(16) -0.0017(16) 0.0001(16) C3 0.021(2) 0.033(2) 0.038(2) -0.0037(18) 0.0068(19) -0.0066(17) C4 0.023(2) 0.0224(18) 0.032(2) -0.0014(16) 0.0039(17) -0.0040(16) C5 0.021(2) 0.0242(18) 0.0212(18) -0.0073(15) 0.0035(15) -0.0041(16) C6 0.0142(19) 0.029(2) 0.0249(19) -0.0031(15) 0.0057(15) 0.0003(15) C7 0.022(2) 0.0256(19) 0.0264(19) -0.0011(15) 0.0040(16) -0.0009(16) C8 0.030(2) 0.0255(19) 0.029(2) -0.0015(16) 0.0052(18) 0.0029(17) C9 0.028(2) 0.039(2) 0.027(2) -0.0016(17) 0.0105(18) 0.0026(19) C10 0.029(2) 0.041(2) 0.022(2) 0.0061(17) 0.0117(18) 0.0022(19) C11 0.024(2) 0.0283(19) 0.027(2) 0.0029(16) 0.0087(17) 0.0007(16) C12 0.050(3) 0.028(2) 0.032(2) 0.0059(18) 0.009(2) 0.008(2) C13 0.018(2) 0.0237(18) 0.0154(16) -0.0048(14) 0.0033(14) -0.0037(15) C14 0.023(2) 0.0215(18) 0.0165(17) -0.0025(14) 0.0023(15) -0.0035(15) C15 0.034(2) 0.0253(19) 0.0198(18) -0.0014(15) 0.0097(17) -0.0087(17) C16 0.021(2) 0.029(2) 0.035(2) -0.0039(16) 0.0112(18) -0.0071(17) C17 0.020(2) 0.032(2) 0.032(2) -0.0030(17) 0.0048(17) -0.0002(17) C18 0.021(2) 0.0268(19) 0.0221(19) -0.0063(15) 0.0032(16) 0.0004(16) C19 0.021(2) 0.0286(19) 0.0229(19) 0.0060(15) 0.0007(16) -0.0038(16) C20 0.032(3) 0.029(2) 0.032(2) 0.0024(17) -0.0012(19) 0.0036(18) C21 0.046(3) 0.040(2) 0.027(2) -0.0043(18) -0.013(2) 0.000(2) C22 0.020(2) 0.030(2) 0.025(2) 0.0011(15) 0.0052(16) 0.0040(16) C23 0.034(3) 0.028(2) 0.034(2) 0.0033(17) 0.0064(19) 0.0023(18) C24 0.033(3) 0.050(3) 0.029(2) 0.001(2) -0.002(2) 0.008(2) C25 0.025(2) 0.0257(19) 0.0210(18) 0.0010(15) 0.0019(16) -0.0063(16) C26 0.027(2) 0.0200(18) 0.0231(19) 0.0000(14) -0.0017(16) -0.0037(15) C27 0.034(3) 0.028(2) 0.033(2) -0.0079(17) -0.0017(19) 0.0013(18) C28 0.040(3) 0.039(2) 0.022(2) -0.0086(17) 0.0047(19) 0.000(2) C29 0.036(3) 0.032(2) 0.0152(18) -0.0040(15) -0.0015(17) -0.0031(18) C30 0.029(2) 0.035(2) 0.0191(19) 0.0010(16) -0.0048(17) -0.0017(18) C31 0.024(2) 0.043(2) 0.029(2) 0.0015(18) -0.0048(18) -0.0045(18) C32 0.026(2) 0.034(2) 0.030(2) -0.0025(17) 0.0018(18) -0.0073(18) N1 0.0177(17) 0.0194(15) 0.0176(14) 0.0006(12) 0.0038(12) -0.0026(12) N2 0.0207(18) 0.0250(16) 0.0193(15) -0.0047(12) 0.0024(13) -0.0010(13) O1 0.0380(18) 0.0274(14) 0.0222(14) 0.0030(11) 0.0045(13) 0.0027(12) Rh1 0.02079(18) 0.02148(16) 0.01398(15) 0.00089(10) 0.00135(11) -0.00067(12) Cl1 0.0205(5) 0.0145(4) 0.0158(4) 0.0013(3) 0.0079(3) -0.0003(3) _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 N2 1.348(5) . ? C1 N1 1.359(4) . ? C1 Rh1 2.052(4) . ? C2 N2 1.486(5) . ? C2 C3 1.510(6) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.532(6) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.507(5) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 N1 1.495(5) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C11 1.373(5) . ? C6 C7 1.412(5) . ? C6 N2 1.446(5) . ? C7 O1 1.369(5) . ? C7 C8 1.385(5) . ? C8 C9 1.393(6) . ? C8 H8 0.9500 . ? C9 C10 1.373(6) . ? C9 H9 0.9500 . ? C10 C11 1.407(6) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 O1 1.427(5) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C18 1.403(5) . ? C13 C14 1.409(5) . ? C13 N1 1.452(4) . ? C14 C15 1.393(5) . ? C14 C19 1.522(6) . ? C15 C16 1.382(6) . ? C15 H15 0.9500 . ? C16 C17 1.383(6) . ? C16 H16 0.9500 . ? C17 C18 1.400(6) . ? C17 H17 0.9500 . ? C18 C22 1.513(5) . ? C19 C21 1.519(6) . ? C19 C20 1.520(6) . ? C19 H19 1.0000 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 C24 1.526(6) . ? C22 C23 1.539(5) . ? C22 H22 1.0000 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 C26 1.399(6) . ? C25 C32 1.515(6) . ? C25 Rh1 2.104(4) . ? C25 H25 0.9500 . ? C26 C27 1.525(5) . ? C26 Rh1 2.130(4) . ? C26 H26 0.9500 . ? C27 C28 1.539(6) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 C29 1.511(6) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 C30 1.386(6) . ? C29 Rh1 2.179(4) . ? C29 H29 0.9500 . ? C30 C31 1.512(6) . ? C30 Rh1 2.216(4) . ? C30 H30 0.9500 . ? C31 C32 1.542(6) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? Rh1 Cl1 2.4628(8) . ? 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 117.8(3) . . ? N2 C1 Rh1 115.3(2) . . ? N1 C1 Rh1 125.2(3) . . ? N2 C2 C3 112.1(3) . . ? N2 C2 H2A 109.2 . . ? C3 C2 H2A 109.2 . . ? N2 C2 H2B 109.2 . . ? C3 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? C2 C3 C4 110.8(3) . . ? C2 C3 H3A 109.5 . . ? C4 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? C5 C4 C3 112.8(3) . . ? C5 C4 H4A 109.0 . . ? C3 C4 H4A 109.0 . . ? C5 C4 H4B 109.0 . . ? C3 C4 H4B 109.0 . . ? H4A C4 H4B 107.8 . . ? N1 C5 C4 113.0(3) . . ? N1 C5 H5A 109.0 . . ? C4 C5 H5A 109.0 . . ? N1 C5 H5B 109.0 . . ? C4 C5 H5B 109.0 . . ? H5A C5 H5B 107.8 . . ? C11 C6 C7 120.5(3) . . ? C11 C6 N2 121.7(3) . . ? C7 C6 N2 117.7(3) . . ? O1 C7 C8 124.4(4) . . ? O1 C7 C6 115.9(3) . . ? C8 C7 C6 119.6(4) . . ? C7 C8 C9 119.2(4) . . ? C7 C8 H8 120.4 . . ? C9 C8 H8 120.4 . . ? C10 C9 C8 121.5(4) . . ? C10 C9 H9 119.3 . . ? C8 C9 H9 119.3 . . ? C9 C10 C11 119.5(4) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C6 C11 C10 119.6(4) . . ? C6 C11 H11 120.2 . . ? C10 C11 H11 120.2 . . ? O1 C12 H12A 109.5 . . ? O1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C18 C13 C14 121.6(3) . . ? C18 C13 N1 120.6(3) . . ? C14 C13 N1 117.6(3) . . ? C15 C14 C13 118.1(4) . . ? C15 C14 C19 119.2(3) . . ? C13 C14 C19 122.7(3) . . ? C16 C15 C14 121.3(4) . . ? C16 C15 H15 119.3 . . ? C14 C15 H15 119.3 . . ? C15 C16 C17 119.6(4) . . ? C15 C16 H16 120.2 . . ? C17 C16 H16 120.2 . . ? C16 C17 C18 121.6(4) . . ? C16 C17 H17 119.2 . . ? C18 C17 H17 119.2 . . ? C17 C18 C13 117.5(4) . . ? C17 C18 C22 118.9(4) . . ? C13 C18 C22 123.5(3) . . ? C21 C19 C20 110.0(3) . . ? C21 C19 C14 111.5(3) . . ? C20 C19 C14 112.7(3) . . ? C21 C19 H19 107.4 . . ? C20 C19 H19 107.4 . . ? C14 C19 H19 107.4 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C18 C22 C24 111.9(4) . . ? C18 C22 C23 110.1(3) . . ? C24 C22 C23 109.5(3) . . ? C18 C22 H22 108.4 . . ? C24 C22 H22 108.4 . . ? C23 C22 H22 108.4 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C26 C25 C32 125.3(4) . . ? C26 C25 Rh1 71.7(2) . . ? C32 C25 Rh1 111.0(3) . . ? C26 C25 H25 117.4 . . ? C32 C25 H25 117.4 . . ? Rh1 C25 H25 87.3 . . ? C25 C26 C27 124.2(4) . . ? C25 C26 Rh1 69.7(2) . . ? C27 C26 Rh1 113.8(3) . . ? C25 C26 H26 117.9 . . ? C27 C26 H26 117.9 . . ? Rh1 C26 H26 86.5 . . ? C26 C27 C28 112.1(3) . . ? C26 C27 H27A 109.2 . . ? C28 C27 H27A 109.2 . . ? C26 C27 H27B 109.2 . . ? C28 C27 H27B 109.2 . . ? H27A C27 H27B 107.9 . . ? C29 C28 C27 114.2(3) . . ? C29 C28 H28A 108.7 . . ? C27 C28 H28A 108.7 . . ? C29 C28 H28B 108.7 . . ? C27 C28 H28B 108.7 . . ? H28A C28 H28B 107.6 . . ? C30 C29 C28 124.9(4) . . ? C30 C29 Rh1 73.1(2) . . ? C28 C29 Rh1 108.6(3) . . ? C30 C29 H29 117.5 . . ? C28 C29 H29 117.5 . . ? Rh1 C29 H29 88.3 . . ? C29 C30 C31 123.5(4) . . ? C29 C30 Rh1 70.1(2) . . ? C31 C30 Rh1 111.6(3) . . ? C29 C30 H30 118.3 . . ? C31 C30 H30 118.3 . . ? Rh1 C30 H30 88.3 . . ? C30 C31 C32 112.1(3) . . ? C30 C31 H31A 109.2 . . ? C32 C31 H31A 109.2 . . ? C30 C31 H31B 109.2 . . ? C32 C31 H31B 109.2 . . ? H31A C31 H31B 107.9 . . ? C25 C32 C31 113.4(3) . . ? C25 C32 H32A 108.9 . . ? C31 C32 H32A 108.9 . . ? C25 C32 H32B 108.9 . . ? C31 C32 H32B 108.9 . . ? H32A C32 H32B 107.7 . . ? C1 N1 C13 118.2(3) . . ? C1 N1 C5 128.0(3) . . ? C13 N1 C5 113.7(3) . . ? C1 N2 C6 118.7(3) . . ? C1 N2 C2 125.3(3) . . ? C6 N2 C2 115.2(3) . . ? C7 O1 C12 115.9(3) . . ? C1 Rh1 C25 99.07(14) . . ? C1 Rh1 C26 98.62(14) . . ? C25 Rh1 C26 38.58(15) . . ? C1 Rh1 C29 153.58(16) . . ? C25 Rh1 C29 97.52(16) . . ? C26 Rh1 C29 81.93(15) . . ? C1 Rh1 C30 167.57(15) . . ? C25 Rh1 C30 81.51(15) . . ? C26 Rh1 C30 89.57(15) . . ? C29 Rh1 C30 36.76(16) . . ? C1 Rh1 Cl1 85.12(9) . . ? C25 Rh1 Cl1 151.25(11) . . ? C26 Rh1 Cl1 169.02(10) . . ? C29 Rh1 Cl1 90.14(11) . . ? C30 Rh1 Cl1 88.56(11) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.528 _refine_diff_density_min -0.868 _refine_diff_density_rms 0.118 # Attachment 'kjc0839b.cif' data_kjc0839b _database_code_depnum_ccdc_archive 'CCDC 733103' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H33 N2 O, I' _chemical_formula_sum 'C24 H33 I N2 O' _chemical_formula_weight 492.42 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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.4370(3) _cell_length_b 19.2770(7) _cell_length_c 23.4090(8) _cell_angle_alpha 90.00 _cell_angle_beta 91.811(2) _cell_angle_gamma 90.00 _cell_volume 4707.4(3) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3841 _cell_measurement_theta_min 1.37 _cell_measurement_theta_max 27.47 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.390 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2016 _exptl_absorpt_coefficient_mu 1.376 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6750 _exptl_absorpt_correction_T_max 0.9220 _exptl_absorpt_process_details Denzo/Scalepack _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'CCD scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17345 _diffrn_reflns_av_R_equivalents 0.1598 _diffrn_reflns_av_sigmaI/netI 0.3089 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.37 _diffrn_reflns_theta_max 27.47 _reflns_number_total 10448 _reflns_number_gt 3841 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'cOLLECT,Nonius BV, 1997-2001' _computing_cell_refinement DENZO/SCALEPACK _computing_data_reduction DENZO/SCALEPACK _computing_structure_solution SHELXs-97 _computing_structure_refinement SHELXL-97 _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^)+(0.0163P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10448 _refine_ls_number_parameters 515 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2460 _refine_ls_R_factor_gt 0.0739 _refine_ls_wR_factor_ref 0.1386 _refine_ls_wR_factor_gt 0.1007 _refine_ls_goodness_of_fit_ref 0.909 _refine_ls_restrained_S_all 0.909 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C36 C 1.3457(9) 1.0283(4) 0.5106(3) 0.050(3) Uani 1 1 d . . . H36A H 1.4307 1.0438 0.4993 0.074 Uiso 1 1 calc R . . H36B H 1.3251 0.9840 0.4920 0.074 Uiso 1 1 calc R . . H36C H 1.3454 1.0224 0.5521 0.074 Uiso 1 1 calc R . . I1 I 0.46613(6) 0.88207(3) 0.12161(2) 0.03793(19) Uani 1 1 d . . . I2 I 0.96311(6) 0.63031(3) 0.11034(2) 0.0411(2) Uani 1 1 d . . . C1 C 0.8329(8) 0.8713(4) 0.1141(3) 0.030(2) Uani 1 1 d . . . H1 H 0.7420 0.8722 0.1145 0.036 Uiso 1 1 calc R . . C2 C 1.0231(8) 0.8273(4) 0.0675(3) 0.031(2) Uani 1 1 d . . . H2A H 1.0373 0.7943 0.0360 0.037 Uiso 1 1 calc R . . H2B H 1.0517 0.8048 0.1037 0.037 Uiso 1 1 calc R . . C3 C 1.1026(8) 0.8914(4) 0.0585(3) 0.031(2) Uani 1 1 d . . . H3A H 1.0861 0.9089 0.0192 0.038 Uiso 1 1 calc R . . H3B H 1.1946 0.8792 0.0625 0.038 Uiso 1 1 calc R . . C4 C 1.0718(8) 0.9493(4) 0.1018(3) 0.032(2) Uani 1 1 d . . . H4A H 1.1488 0.9788 0.1076 0.038 Uiso 1 1 calc R . . H4B H 1.0027 0.9789 0.0851 0.038 Uiso 1 1 calc R . . C5 C 1.0305(8) 0.9231(4) 0.1598(3) 0.032(2) Uani 1 1 d . . . H5A H 1.0869 0.8842 0.1720 0.039 Uiso 1 1 calc R . . H5B H 1.0416 0.9607 0.1882 0.039 Uiso 1 1 calc R . . C6 C 0.8033(8) 0.8327(4) 0.0195(3) 0.031(2) Uani 1 1 d . . . C7 C 0.7368(8) 0.8908(4) -0.0030(3) 0.033(2) Uani 1 1 d . . . C8 C 0.6512(8) 0.8809(5) -0.0491(3) 0.045(3) Uani 1 1 d . . . H8 H 0.6005 0.9183 -0.0635 0.054 Uiso 1 1 calc R . . C9 C 0.6408(10) 0.8163(5) -0.0736(3) 0.053(3) Uani 1 1 d . . . H9 H 0.5824 0.8096 -0.1051 0.064 Uiso 1 1 calc R . . C10 C 0.7123(9) 0.7616(5) -0.0539(3) 0.041(3) Uani 1 1 d . . . H10 H 0.7054 0.7178 -0.0724 0.050 Uiso 1 1 calc R . . C11 C 0.7952(8) 0.7698(4) -0.0069(3) 0.036(2) Uani 1 1 d . . . H11 H 0.8457 0.7320 0.0068 0.043 Uiso 1 1 calc R . . C12 C 0.6728(9) 1.0076(4) 0.0138(3) 0.049(3) Uani 1 1 d . . . H12A H 0.6656 1.0177 -0.0272 0.073 Uiso 1 1 calc R . . H12B H 0.7026 1.0492 0.0343 0.073 Uiso 1 1 calc R . . H12C H 0.5888 0.9939 0.0275 0.073 Uiso 1 1 calc R . . C13 C 0.8230(7) 0.9134(4) 0.2105(3) 0.024(2) Uani 1 1 d . . . C14 C 0.8144(8) 0.8603(4) 0.2496(3) 0.026(2) Uani 1 1 d . . . C15 C 0.7530(8) 0.8756(4) 0.2998(3) 0.039(2) Uani 1 1 d . . . H15 H 0.7447 0.8406 0.3280 0.047 Uiso 1 1 calc R . . C16 C 0.7036(9) 0.9415(4) 0.3094(3) 0.042(3) Uani 1 1 d . . . H16 H 0.6626 0.9511 0.3441 0.050 Uiso 1 1 calc R . . C17 C 0.7136(8) 0.9924(4) 0.2691(3) 0.036(2) Uani 1 1 d . . . H17 H 0.6784 1.0369 0.2762 0.043 Uiso 1 1 calc R . . C18 C 0.7745(8) 0.9805(4) 0.2176(3) 0.027(2) Uani 1 1 d . . . C19 C 0.8598(8) 0.7874(4) 0.2382(3) 0.031(2) Uani 1 1 d . . . H19 H 0.9268 0.7901 0.2087 0.037 Uiso 1 1 calc R . . C20 C 0.7477(8) 0.7446(4) 0.2129(3) 0.042(3) Uani 1 1 d . . . H20A H 0.6800 0.7415 0.2409 0.064 Uiso 1 1 calc R . . H20B H 0.7778 0.6979 0.2037 0.064 Uiso 1 1 calc R . . H20C H 0.7138 0.7671 0.1781 0.064 Uiso 1 1 calc R . . C21 C 0.9194(8) 0.7511(4) 0.2908(3) 0.047(3) Uani 1 1 d . . . H21A H 0.9822 0.7820 0.3097 0.070 Uiso 1 1 calc R . . H21B H 0.9621 0.7084 0.2790 0.070 Uiso 1 1 calc R . . H21C H 0.8520 0.7397 0.3175 0.070 Uiso 1 1 calc R . . C22 C 0.7767(8) 1.0365(4) 0.1727(3) 0.033(2) Uani 1 1 d . . . H22 H 0.8059 1.0149 0.1365 0.040 Uiso 1 1 calc R . . C23 C 0.6446(8) 1.0672(4) 0.1606(3) 0.041(2) Uani 1 1 d . . . H23A H 0.5849 1.0302 0.1489 0.061 Uiso 1 1 calc R . . H23B H 0.6494 1.1016 0.1299 0.061 Uiso 1 1 calc R . . H23C H 0.6142 1.0897 0.1952 0.061 Uiso 1 1 calc R . . C24 C 0.8732(9) 1.0927(4) 0.1899(3) 0.049(3) Uani 1 1 d . . . H24A H 0.8457 1.1157 0.2248 0.074 Uiso 1 1 calc R . . H24B H 0.8782 1.1269 0.1591 0.074 Uiso 1 1 calc R . . H24C H 0.9577 1.0717 0.1970 0.074 Uiso 1 1 calc R . . C25 C 1.1658(8) 1.1445(4) 0.3959(3) 0.031(2) Uani 1 1 d . . . H25 H 1.2568 1.1448 0.3951 0.037 Uiso 1 1 calc R . . C26 C 0.9742(8) 1.1919(4) 0.4410(3) 0.029(2) Uani 1 1 d . . . H26A H 0.9435 1.2109 0.4037 0.035 Uiso 1 1 calc R . . H26B H 0.9596 1.2274 0.4706 0.035 Uiso 1 1 calc R . . C27 C 0.8972(9) 1.1271(4) 0.4545(3) 0.042(2) Uani 1 1 d . . . H27A H 0.8045 1.1377 0.4504 0.050 Uiso 1 1 calc R . . H27B H 0.9158 1.1131 0.4946 0.050 Uiso 1 1 calc R . . C28 C 0.9299(9) 1.0667(4) 0.4143(3) 0.042(2) Uani 1 1 d . . . H28A H 1.0007 1.0395 0.4323 0.050 Uiso 1 1 calc R . . H28B H 0.8544 1.0359 0.4104 0.050 Uiso 1 1 calc R . . C29 C 0.9685(8) 1.0883(4) 0.3557(3) 0.034(2) Uani 1 1 d . . . H29A H 0.9557 1.0487 0.3292 0.041 Uiso 1 1 calc R . . H29B H 0.9120 1.1265 0.3421 0.041 Uiso 1 1 calc R . . C30 C 1.1963(8) 1.1964(4) 0.4867(3) 0.028(2) Uani 1 1 d . . . C31 C 1.2716(8) 1.1450(4) 0.5123(3) 0.029(2) Uani 1 1 d . . . C32 C 1.3597(8) 1.1652(4) 0.5561(3) 0.034(2) Uani 1 1 d . . . H32 H 1.4160 1.1318 0.5730 0.040 Uiso 1 1 calc R . . C33 C 1.3649(9) 1.2325(5) 0.5744(3) 0.042(3) Uani 1 1 d . . . H33 H 1.4235 1.2452 0.6045 0.050 Uiso 1 1 calc R . . C34 C 1.2868(9) 1.2816(4) 0.5500(3) 0.041(3) Uani 1 1 d . . . H34 H 1.2916 1.3282 0.5633 0.049 Uiso 1 1 calc R . . C35 C 1.2005(9) 1.2643(4) 0.5060(3) 0.032(2) Uani 1 1 d . . . H35 H 1.1451 1.2984 0.4895 0.039 Uiso 1 1 calc R . . C37 C 1.1752(8) 1.0919(4) 0.3038(3) 0.024(2) Uani 1 1 d . . . C38 C 1.1900(8) 1.1419(4) 0.2615(3) 0.028(2) Uani 1 1 d . . . C39 C 1.2493(8) 1.1217(4) 0.2124(3) 0.034(2) Uani 1 1 d . . . H39 H 1.2584 1.1540 0.1821 0.040 Uiso 1 1 calc R . . C40 C 1.2959(8) 1.0542(5) 0.2069(3) 0.043(2) Uani 1 1 d . . . H40 H 1.3368 1.0411 0.1729 0.051 Uiso 1 1 calc R . . C41 C 1.2835(9) 1.0064(4) 0.2502(3) 0.041(3) Uani 1 1 d . . . H41 H 1.3162 0.9607 0.2458 0.050 Uiso 1 1 calc R . . C42 C 1.2232(8) 1.0244(4) 0.3006(3) 0.030(2) Uani 1 1 d . . . C43 C 1.1503(8) 1.2174(4) 0.2687(3) 0.032(2) Uani 1 1 d . . . H43 H 1.0839 1.2186 0.2985 0.038 Uiso 1 1 calc R . . C44 C 1.0902(8) 1.2505(4) 0.2144(3) 0.043(3) Uani 1 1 d . . . H44A H 1.1553 1.2545 0.1853 0.065 Uiso 1 1 calc R . . H44B H 1.0575 1.2967 0.2235 0.065 Uiso 1 1 calc R . . H44C H 1.0195 1.2214 0.1998 0.065 Uiso 1 1 calc R . . C45 C 1.2641(8) 1.2605(4) 0.2912(3) 0.044(3) Uani 1 1 d . . . H45A H 1.3050 1.2370 0.3241 0.066 Uiso 1 1 calc R . . H45B H 1.2339 1.3063 0.3029 0.066 Uiso 1 1 calc R . . H45C H 1.3263 1.2658 0.2610 0.066 Uiso 1 1 calc R . . C46 C 1.2119(9) 0.9713(4) 0.3479(3) 0.045(3) Uani 1 1 d . . . H46 H 1.1784 0.9957 0.3821 0.054 Uiso 1 1 calc R . . C47 C 1.1153(9) 0.9129(4) 0.3310(4) 0.061(3) Uani 1 1 d . . . H47A H 1.0348 0.9337 0.3167 0.091 Uiso 1 1 calc R . . H47B H 1.0988 0.8842 0.3645 0.091 Uiso 1 1 calc R . . H47C H 1.1514 0.8841 0.3010 0.091 Uiso 1 1 calc R . . C48 C 1.3453(8) 0.9419(4) 0.3648(3) 0.048(3) Uani 1 1 d . . . H48A H 1.3815 0.9187 0.3317 0.071 Uiso 1 1 calc R . . H48B H 1.3370 0.9084 0.3960 0.071 Uiso 1 1 calc R . . H48C H 1.4020 0.9798 0.3774 0.071 Uiso 1 1 calc R . . O1 O 0.7626(5) 0.9524(3) 0.0236(2) 0.0382(15) Uani 1 1 d . . . O2 O 1.2516(6) 1.0792(3) 0.4934(2) 0.0389(16) Uani 1 1 d . . . N1 N 0.8839(7) 0.8431(3) 0.0697(2) 0.0264(17) Uani 1 1 d . . . N2 N 0.8949(6) 0.8992(3) 0.1590(2) 0.0237(16) Uani 1 1 d . . . N3 N 1.1126(6) 1.1774(3) 0.4387(2) 0.0254(16) Uani 1 1 d . . . N4 N 1.1029(6) 1.1113(3) 0.3541(2) 0.0246(16) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C36 0.048(8) 0.031(6) 0.069(6) 0.023(4) -0.001(5) 0.003(5) I1 0.0312(4) 0.0360(3) 0.0465(4) 0.0011(3) -0.0009(3) -0.0025(3) I2 0.0329(5) 0.0367(4) 0.0538(4) -0.0023(3) 0.0023(3) -0.0004(3) C1 0.037(6) 0.029(5) 0.023(5) -0.001(4) 0.002(4) 0.002(4) C2 0.028(7) 0.031(5) 0.033(5) -0.007(4) 0.006(4) 0.006(4) C3 0.014(5) 0.045(5) 0.035(5) 0.001(4) 0.010(4) -0.002(4) C4 0.020(6) 0.029(5) 0.047(5) -0.008(4) 0.006(4) -0.010(4) C5 0.042(7) 0.029(5) 0.025(5) -0.012(4) 0.001(4) -0.003(4) C6 0.032(6) 0.043(6) 0.020(5) -0.007(4) 0.015(4) -0.013(5) C7 0.032(6) 0.038(6) 0.029(5) 0.000(4) 0.010(4) -0.013(5) C8 0.040(7) 0.069(7) 0.025(5) 0.004(5) 0.000(4) -0.008(6) C9 0.057(8) 0.081(8) 0.022(5) -0.002(5) 0.003(5) -0.033(7) C10 0.053(8) 0.042(6) 0.030(5) -0.004(4) 0.004(5) -0.021(5) C11 0.032(7) 0.052(6) 0.024(5) -0.001(4) 0.005(4) -0.007(5) C12 0.044(7) 0.039(6) 0.064(6) 0.016(5) 0.007(5) -0.006(5) C13 0.011(5) 0.035(5) 0.027(5) 0.002(4) 0.005(4) -0.007(4) C14 0.026(6) 0.034(5) 0.020(4) -0.008(4) 0.006(4) -0.009(4) C15 0.047(7) 0.034(6) 0.036(5) 0.005(4) -0.006(4) -0.013(5) C16 0.052(8) 0.047(6) 0.027(5) -0.009(4) 0.010(4) -0.014(5) C17 0.039(7) 0.042(6) 0.028(5) -0.014(4) 0.012(4) -0.001(5) C18 0.026(6) 0.017(5) 0.038(5) -0.002(4) -0.004(4) -0.003(4) C19 0.036(7) 0.024(5) 0.033(5) 0.006(4) -0.004(4) -0.004(4) C20 0.039(7) 0.037(6) 0.051(6) -0.011(4) 0.007(5) 0.005(5) C21 0.048(8) 0.038(5) 0.055(6) 0.007(4) 0.018(5) 0.008(5) C22 0.032(6) 0.025(5) 0.042(5) -0.003(4) 0.004(4) -0.008(4) C23 0.033(7) 0.036(5) 0.053(6) -0.003(4) 0.003(5) 0.004(5) C24 0.059(8) 0.032(5) 0.055(6) 0.014(4) -0.012(5) -0.023(5) C25 0.038(7) 0.027(5) 0.029(5) 0.014(4) 0.005(4) 0.005(4) C26 0.023(6) 0.030(5) 0.034(5) -0.005(4) 0.005(4) 0.008(4) C27 0.028(6) 0.061(6) 0.037(5) -0.007(5) 0.004(4) -0.005(5) C28 0.045(7) 0.039(6) 0.042(6) 0.000(4) 0.009(5) -0.014(5) C29 0.032(7) 0.028(5) 0.041(6) -0.001(4) -0.004(5) -0.002(4) C30 0.038(6) 0.027(5) 0.018(5) -0.001(4) 0.005(4) -0.010(4) C31 0.028(6) 0.036(6) 0.024(5) 0.005(4) 0.005(4) 0.001(5) C32 0.031(6) 0.043(6) 0.026(5) 0.010(4) 0.000(4) 0.006(5) C33 0.046(7) 0.054(6) 0.025(5) -0.007(4) -0.010(5) -0.006(5) C34 0.059(8) 0.049(6) 0.015(5) -0.006(4) 0.010(5) -0.010(5) C35 0.052(7) 0.025(5) 0.021(5) 0.008(4) 0.007(4) 0.003(5) C37 0.021(6) 0.027(5) 0.025(5) -0.002(4) -0.002(4) -0.002(4) C38 0.029(6) 0.029(5) 0.025(5) -0.006(4) -0.001(4) -0.012(4) C39 0.027(6) 0.050(6) 0.025(5) 0.005(4) 0.001(4) -0.012(5) C40 0.026(7) 0.064(7) 0.038(6) -0.013(5) 0.010(4) -0.009(5) C41 0.050(8) 0.020(5) 0.054(6) -0.009(4) 0.002(5) 0.002(5) C42 0.034(6) 0.026(5) 0.029(5) -0.008(4) -0.001(4) -0.012(4) C43 0.025(6) 0.038(5) 0.032(5) 0.007(4) 0.004(4) -0.008(4) C44 0.035(7) 0.042(5) 0.052(6) 0.013(4) -0.013(5) -0.006(5) C45 0.047(8) 0.022(5) 0.065(6) -0.010(4) 0.008(5) -0.008(5) C46 0.058(8) 0.034(5) 0.043(6) -0.002(4) 0.006(5) 0.001(5) C47 0.068(9) 0.031(6) 0.083(7) 0.002(5) -0.005(6) -0.024(5) C48 0.043(7) 0.035(5) 0.064(6) -0.008(4) -0.008(5) 0.007(5) O1 0.030(4) 0.031(4) 0.053(4) 0.007(3) -0.004(3) 0.004(3) O2 0.051(5) 0.023(3) 0.042(3) 0.004(3) -0.002(3) 0.015(3) N1 0.032(5) 0.023(4) 0.024(4) -0.003(3) 0.002(3) 0.001(3) N2 0.027(5) 0.021(4) 0.023(4) 0.004(3) -0.001(3) -0.001(3) N3 0.015(5) 0.028(4) 0.033(4) -0.002(3) 0.006(3) -0.001(3) N4 0.023(5) 0.025(4) 0.026(4) -0.003(3) -0.003(3) 0.000(3) _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 C36 O2 1.437(8) . ? C1 N1 1.302(9) . ? C1 N2 1.329(8) . ? C2 N1 1.486(9) . ? C2 C3 1.506(10) . ? C3 C4 1.549(9) . ? C4 C5 1.523(9) . ? C5 N2 1.489(9) . ? C6 C11 1.362(10) . ? C6 C7 1.410(10) . ? C6 N1 1.439(9) . ? C7 O1 1.363(8) . ? C7 C8 1.393(10) . ? C8 C9 1.373(11) . ? C9 C10 1.364(11) . ? C10 C11 1.387(10) . ? C12 O1 1.432(9) . ? C13 C14 1.378(9) . ? C13 C18 1.400(9) . ? C13 N2 1.467(9) . ? C14 C15 1.388(10) . ? C14 C19 1.508(9) . ? C15 C16 1.391(10) . ? C16 C17 1.368(10) . ? C17 C18 1.398(10) . ? C18 C22 1.508(9) . ? C19 C21 1.532(9) . ? C19 C20 1.534(10) . ? C22 C23 1.519(10) . ? C22 C24 1.526(9) . ? C25 N3 1.323(9) . ? C25 N4 1.326(8) . ? C26 N3 1.474(9) . ? C26 C27 1.523(10) . ? C27 C28 1.542(10) . ? C28 C29 1.500(10) . ? C29 N4 1.473(9) . ? C30 C35 1.384(9) . ? C30 C31 1.388(10) . ? C30 N3 1.448(9) . ? C31 O2 1.356(8) . ? C31 C32 1.411(10) . ? C32 C33 1.367(10) . ? C33 C34 1.363(10) . ? C34 C35 1.388(10) . ? C37 C38 1.393(9) . ? C37 C42 1.397(9) . ? C37 N4 1.467(9) . ? C38 C39 1.378(10) . ? C38 C43 1.525(9) . ? C39 C40 1.397(10) . ? C40 C41 1.381(10) . ? C41 C42 1.398(11) . ? C42 C46 1.515(10) . ? C43 C45 1.530(10) . ? C43 C44 1.538(9) . ? C46 C48 1.543(11) . ? C46 C47 1.555(10) . ? 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 126.8(8) . . ? N1 C2 C3 112.4(6) . . ? C2 C3 C4 111.9(6) . . ? C5 C4 C3 114.5(6) . . ? N2 C5 C4 112.8(6) . . ? C11 C6 C7 121.0(7) . . ? C11 C6 N1 121.3(8) . . ? C7 C6 N1 117.6(7) . . ? O1 C7 C8 125.9(8) . . ? O1 C7 C6 115.7(7) . . ? C8 C7 C6 118.4(7) . . ? C9 C8 C7 119.2(8) . . ? C10 C9 C8 121.6(8) . . ? C9 C10 C11 120.0(8) . . ? C6 C11 C10 119.3(8) . . ? C14 C13 C18 125.2(7) . . ? C14 C13 N2 116.9(7) . . ? C18 C13 N2 117.8(6) . . ? C13 C14 C15 116.4(7) . . ? C13 C14 C19 123.2(7) . . ? C15 C14 C19 120.3(7) . . ? C14 C15 C16 121.0(7) . . ? C17 C16 C15 120.5(8) . . ? C16 C17 C18 121.5(8) . . ? C17 C18 C13 115.5(7) . . ? C17 C18 C22 120.0(7) . . ? C13 C18 C22 124.4(7) . . ? C14 C19 C21 113.9(6) . . ? C14 C19 C20 109.2(7) . . ? C21 C19 C20 110.5(6) . . ? C18 C22 C23 112.1(7) . . ? C18 C22 C24 110.4(6) . . ? C23 C22 C24 111.1(7) . . ? N3 C25 N4 125.5(8) . . ? N3 C26 C27 112.2(6) . . ? C26 C27 C28 111.3(7) . . ? C29 C28 C27 114.8(6) . . ? N4 C29 C28 112.9(6) . . ? C35 C30 C31 121.5(7) . . ? C35 C30 N3 120.2(7) . . ? C31 C30 N3 118.2(7) . . ? O2 C31 C30 116.6(7) . . ? O2 C31 C32 125.8(7) . . ? C30 C31 C32 117.6(7) . . ? C33 C32 C31 120.6(8) . . ? C34 C33 C32 120.7(8) . . ? C33 C34 C35 120.6(8) . . ? C30 C35 C34 118.9(8) . . ? C38 C37 C42 123.9(7) . . ? C38 C37 N4 117.8(7) . . ? C42 C37 N4 118.3(6) . . ? C39 C38 C37 117.4(7) . . ? C39 C38 C43 119.4(7) . . ? C37 C38 C43 123.1(7) . . ? C38 C39 C40 120.4(7) . . ? C41 C40 C39 120.9(8) . . ? C40 C41 C42 120.6(8) . . ? C37 C42 C41 116.7(7) . . ? C37 C42 C46 123.6(7) . . ? C41 C42 C46 119.7(7) . . ? C38 C43 C45 110.2(7) . . ? C38 C43 C44 114.3(6) . . ? C45 C43 C44 110.6(6) . . ? C42 C46 C48 110.2(8) . . ? C42 C46 C47 111.5(6) . . ? C48 C46 C47 111.8(7) . . ? C7 O1 C12 117.1(6) . . ? C31 O2 C36 116.8(6) . . ? C1 N1 C6 117.9(7) . . ? C1 N1 C2 122.6(6) . . ? C6 N1 C2 119.3(6) . . ? C1 N2 C13 118.5(7) . . ? C1 N2 C5 125.0(6) . . ? C13 N2 C5 116.3(5) . . ? C25 N3 C30 116.8(7) . . ? C25 N3 C26 123.6(6) . . ? C30 N3 C26 119.5(6) . . ? C25 N4 C37 117.4(7) . . ? C25 N4 C29 125.3(7) . . ? C37 N4 C29 117.3(6) . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 0.659 _refine_diff_density_min -0.740 _refine_diff_density_rms 0.135 # Attachment 'kjc0843.cif' data_kjc0843 _database_code_depnum_ccdc_archive 'CCDC 733104' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C36 H42 Cl2 N8 Rh, C H2 Cl2, c8 h12 Rh Cl2' _chemical_formula_sum 'C45 H56 Cl6 N8 Rh2' _chemical_formula_weight 1127.50 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 0.0000 0.0000 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 18.65700(10) _cell_length_b 14.5440(2) _cell_length_c 34.2020(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 9280.62(17) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 7768 _cell_measurement_theta_min 1.87 _cell_measurement_theta_max 27.51 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.614 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4592 _exptl_absorpt_coefficient_mu 1.100 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6674 _exptl_absorpt_correction_T_max 0.9172 _exptl_absorpt_process_details Denzo/Scalepack _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'CCD scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 44612 _diffrn_reflns_av_R_equivalents 0.0685 _diffrn_reflns_av_sigmaI/netI 0.0611 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -44 _diffrn_reflns_limit_l_max 43 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 27.51 _reflns_number_total 10603 _reflns_number_gt 7768 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'cOLLECT,Nonius BV, 1997-2001' _computing_cell_refinement DENZO/SCALEPACK _computing_data_reduction DENZO/SCALEPACK _computing_structure_solution SHELXs-97 _computing_structure_refinement SHELXL-97 _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^)+(0.0282P)^2^+211.1986P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10603 _refine_ls_number_parameters 631 _refine_ls_number_restraints 189 _refine_ls_R_factor_all 0.1485 _refine_ls_R_factor_gt 0.1158 _refine_ls_wR_factor_ref 0.2564 _refine_ls_wR_factor_gt 0.2429 _refine_ls_goodness_of_fit_ref 1.161 _refine_ls_restrained_S_all 1.157 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4274(6) 0.6862(8) 0.1387(3) 0.043(3) Uani 1 1 d . A 1 H1 H 0.4748 0.6932 0.1483 0.052 Uiso 1 1 calc R A 1 C2 C 0.4050(7) 0.7427(8) 0.1097(4) 0.048(3) Uani 1 1 d . A 1 H2 H 0.4362 0.7883 0.0995 0.058 Uiso 1 1 calc R A 1 C3 C 0.3369(8) 0.7335(10) 0.0954(3) 0.055(3) Uani 1 1 d . A 1 H3 H 0.3205 0.7723 0.0749 0.066 Uiso 1 1 calc R A 1 C4 C 0.2918(6) 0.6669(9) 0.1111(3) 0.047(3) Uani 1 1 d . A 1 H4 H 0.2447 0.6582 0.1012 0.056 Uiso 1 1 calc R A 1 C5 C 0.3171(6) 0.6141(8) 0.1414(3) 0.038(2) Uani 1 1 d . A 1 C6 C 0.2014(7) 0.5361(10) 0.1476(4) 0.071(5) Uani 0.73(2) 1 d PD A 1 H6A H 0.2002 0.5391 0.1187 0.085 Uiso 0.73(2) 1 calc PR A 1 H6B H 0.1699 0.5851 0.1580 0.085 Uiso 0.73(2) 1 calc PR A 1 C7 C 0.1747(9) 0.4414(11) 0.1615(5) 0.060(5) Uani 0.73(2) 1 d PDU A 1 H7A H 0.1237 0.4328 0.1543 0.072 Uiso 0.73(2) 1 calc PR A 1 H7B H 0.2031 0.3917 0.1492 0.072 Uiso 0.73(2) 1 calc PR A 1 C8 C 0.1836(8) 0.4389(16) 0.2062(5) 0.046(6) Uani 0.73(2) 1 d PDU A 1 H8A H 0.1543 0.4877 0.2186 0.055 Uiso 0.73(2) 1 calc PR A 1 H8B H 0.1683 0.3786 0.2167 0.055 Uiso 0.73(2) 1 calc PR A 1 C9 C 0.3038(5) 0.5079(7) 0.1944(3) 0.033(2) Uani 1 1 d . A 1 C10 C 0.2805(5) 0.4094(7) 0.2504(3) 0.035(2) Uani 1 1 d . A 1 C11 C 0.3106(5) 0.3211(7) 0.2502(4) 0.039(3) Uani 1 1 d . A 1 C12 C 0.3264(6) 0.2793(8) 0.2854(4) 0.043(3) Uani 1 1 d . A 1 H12 H 0.3495 0.2211 0.2855 0.052 Uiso 1 1 calc R A 1 C13 C 0.3089(7) 0.3208(9) 0.3211(4) 0.054(3) Uani 1 1 d . A 1 C14 C 0.2744(7) 0.4058(9) 0.3201(4) 0.055(3) Uani 1 1 d . A 1 H14 H 0.2604 0.4332 0.3441 0.065 Uiso 1 1 calc R A 1 C15 C 0.2598(5) 0.4518(8) 0.2857(4) 0.042(3) Uani 1 1 d . A 1 C16 C 0.3254(7) 0.2703(8) 0.2128(4) 0.058(4) Uani 1 1 d . A 1 H16A H 0.3480 0.2111 0.2188 0.087 Uiso 1 1 calc R A 1 H16B H 0.3576 0.3069 0.1964 0.087 Uiso 1 1 calc R A 1 H16C H 0.2802 0.2597 0.1989 0.087 Uiso 1 1 calc R A 1 C17 C 0.3287(8) 0.2755(11) 0.3584(4) 0.071(4) Uani 1 1 d . A 1 H17A H 0.3197 0.3177 0.3801 0.107 Uiso 1 1 calc R A 1 H17B H 0.3796 0.2590 0.3578 0.107 Uiso 1 1 calc R A 1 H17C H 0.2998 0.2198 0.3618 0.107 Uiso 1 1 calc R A 1 C18 C 0.2224(7) 0.5437(9) 0.2866(5) 0.060(4) Uani 1 1 d . A 1 H18A H 0.1721 0.5358 0.2791 0.090 Uiso 1 1 calc R A 1 H18B H 0.2459 0.5857 0.2681 0.090 Uiso 1 1 calc R A 1 H18C H 0.2250 0.5695 0.3130 0.090 Uiso 1 1 calc R A 1 C19 C 0.4174(6) 0.5305(10) 0.2919(4) 0.050(3) Uani 1 1 d . A 1 H19 H 0.3901 0.5856 0.2931 0.060 Uiso 1 1 calc R A 1 C20 C 0.4440(6) 0.4951(12) 0.3262(4) 0.062(4) Uani 1 1 d . A 1 H20 H 0.4345 0.5236 0.3507 0.074 Uiso 1 1 calc R A 1 C21 C 0.4863(7) 0.4139(13) 0.3235(5) 0.078(5) Uani 1 1 d . A 1 H21 H 0.5067 0.3878 0.3464 0.093 Uiso 1 1 calc R A 1 C22 C 0.4973(8) 0.3743(11) 0.2888(5) 0.067(5) Uani 1 1 d . A 1 H22 H 0.5243 0.3194 0.2858 0.081 Uiso 1 1 calc R A 1 C23 C 0.4668(6) 0.4186(8) 0.2580(3) 0.045(3) Uani 1 1 d D A 1 C24 C 0.5261(17) 0.300(2) 0.2128(6) 0.105(5) Uani 0.58(2) 1 d PDU A 1 H24A H 0.5023 0.2410 0.2192 0.126 Uiso 0.58(2) 1 calc PR A 1 H24B H 0.5658 0.3094 0.2316 0.126 Uiso 0.58(2) 1 calc PR A 1 C25 C 0.5563(13) 0.2959(18) 0.1709(7) 0.072(7) Uani 0.58(2) 1 d PDU A 1 H25A H 0.5955 0.3414 0.1686 0.087 Uiso 0.58(2) 1 calc PR A 1 H25B H 0.5772 0.2342 0.1665 0.087 Uiso 0.58(2) 1 calc PR A 1 C26 C 0.5009(13) 0.3150(13) 0.1385(5) 0.093(5) Uani 0.58(2) 1 d PDU A 1 H26A H 0.5253 0.3254 0.1132 0.111 Uiso 0.58(2) 1 calc PR A 1 H26B H 0.4679 0.2620 0.1357 0.111 Uiso 0.58(2) 1 calc PR A 1 C27 C 0.4532(5) 0.4403(7) 0.1872(3) 0.038(2) Uani 1 1 d D A 1 C28 C 0.4525(7) 0.4593(7) 0.1132(3) 0.046(3) Uani 1 1 d D A 1 C29 C 0.5076(8) 0.5137(9) 0.0997(5) 0.071(5) Uani 1 1 d . A 1 C30 C 0.4890(13) 0.5558(10) 0.0630(6) 0.095(8) Uani 1 1 d . A 1 H30 H 0.5235 0.5949 0.0511 0.114 Uiso 1 1 calc R A 1 C31 C 0.4265(12) 0.5438(10) 0.0445(5) 0.079(6) Uani 1 1 d . A 1 C32 C 0.3744(9) 0.4857(10) 0.0611(4) 0.068(4) Uani 1 1 d . A 1 H32 H 0.3292 0.4781 0.0488 0.081 Uiso 1 1 calc R A 1 C33 C 0.3900(7) 0.4398(8) 0.0955(4) 0.048(3) Uani 1 1 d . A 1 C34 C 0.5771(8) 0.5225(11) 0.1189(6) 0.085(6) Uani 1 1 d . A 1 H34A H 0.5920 0.5872 0.1188 0.128 Uiso 1 1 calc R A 1 H34B H 0.6127 0.4855 0.1049 0.128 Uiso 1 1 calc R A 1 H34C H 0.5734 0.5008 0.1460 0.128 Uiso 1 1 calc R A 1 C35 C 0.4128(14) 0.5967(12) 0.0071(5) 0.124(10) Uani 1 1 d . A 1 H35A H 0.4131 0.6628 0.0126 0.187 Uiso 1 1 calc R A 1 H35B H 0.3659 0.5792 -0.0036 0.187 Uiso 1 1 calc R A 1 H35C H 0.4503 0.5824 -0.0120 0.187 Uiso 1 1 calc R A 1 C36 C 0.3361(7) 0.3698(10) 0.1105(4) 0.055(3) Uani 1 1 d . A 1 H36A H 0.2888 0.3832 0.0995 0.082 Uiso 1 1 calc R A 1 H36B H 0.3338 0.3731 0.1391 0.082 Uiso 1 1 calc R A 1 H36C H 0.3511 0.3079 0.1026 0.082 Uiso 1 1 calc R A 1 C37 C 0.3194(10) 0.1139(12) -0.0087(6) 0.100(7) Uani 1 1 d D B 1 H37 H 0.2881 0.0814 0.0083 0.120 Uiso 1 1 calc R B 1 C38 C 0.3718(13) 0.0683(17) -0.0246(5) 0.179(16) Uani 1 1 d D B 1 H38 H 0.3725 0.0036 -0.0207 0.214 Uiso 1 1 calc R B 1 C39 C 0.4328(15) 0.110(2) -0.0491(8) 0.191(16) Uani 1 1 d DU B 1 H39A H 0.4564 0.0593 -0.0633 0.229 Uiso 1 1 calc R B 1 H39B H 0.4105 0.1505 -0.0690 0.229 Uiso 1 1 calc R B 1 C40 C 0.4922(17) 0.166(2) -0.0289(6) 0.197(16) Uani 1 1 d DU B 1 H40A H 0.5381 0.1325 -0.0302 0.236 Uiso 1 1 calc R B 1 H40B H 0.4985 0.2260 -0.0425 0.236 Uiso 1 1 calc R B 1 C41 C 0.4716(9) 0.1833(13) 0.0141(5) 0.132(10) Uani 1 1 d D B 1 H41 H 0.5023 0.1564 0.0331 0.158 Uiso 1 1 calc R B 1 C42 C 0.4176(7) 0.2298(10) 0.0276(4) 0.072(4) Uani 1 1 d D B 1 H42 H 0.4121 0.2331 0.0551 0.087 Uiso 1 1 calc R B 1 C43 C 0.3620(10) 0.2798(10) 0.0022(5) 0.101(7) Uani 1 1 d D B 1 H43A H 0.3873 0.3117 -0.0193 0.121 Uiso 1 1 calc R B 1 H43B H 0.3381 0.3273 0.0183 0.121 Uiso 1 1 calc R B 1 C44 C 0.3046(10) 0.2167(12) -0.0154(7) 0.122(8) Uani 1 1 d D B 1 H44A H 0.3015 0.2283 -0.0439 0.147 Uiso 1 1 calc R B 1 H44B H 0.2575 0.2324 -0.0038 0.147 Uiso 1 1 calc R B 1 N1 N 0.3856(4) 0.6204(6) 0.1545(2) 0.0328(19) Uani 1 1 d . A 1 N2 N 0.2759(5) 0.5502(7) 0.1616(3) 0.042(2) Uani 0.73(2) 1 d P A 1 N3 N 0.2619(4) 0.4547(6) 0.2140(3) 0.037(2) Uani 0.73(2) 1 d PD A 1 N4 N 0.4277(4) 0.4922(6) 0.2576(3) 0.036(2) Uani 1 1 d . A 1 N5 N 0.4721(13) 0.3788(11) 0.2162(3) 0.115(5) Uani 1 1 d DU A 1 N6 N 0.4593(12) 0.4009(9) 0.1508(3) 0.101(5) Uani 1 1 d DU A 1 Cl1 Cl 0.35071(14) 0.68620(18) 0.23378(8) 0.0377(6) Uani 1 1 d . A 1 Cl2 Cl 0.52431(13) 0.61414(19) 0.21372(9) 0.0421(7) Uani 1 1 d . A 1 Cl3 Cl 0.45103(19) 0.0954(4) 0.09826(12) 0.0878(15) Uani 1 1 d . B 1 Cl4 Cl 0.3329(4) -0.0475(3) 0.05100(17) 0.125(2) Uani 1 1 d . B 1 Rh1 Rh 0.40521(4) 0.55180(5) 0.20510(2) 0.0299(2) Uani 1 1 d . A 1 Rh2 Rh 0.39323(6) 0.09035(8) 0.03566(3) 0.0529(3) Uani 1 1 d . B 1 C46 C 0.6451(15) 0.1519(18) 0.0662(9) 0.089(8) Uani 0.723(18) 1 d PU C 1 H46A H 0.6562 0.1435 0.0382 0.107 Uiso 0.723(18) 1 calc PR C 1 H46B H 0.5966 0.1265 0.0710 0.107 Uiso 0.723(18) 1 calc PR C 1 Cl5 Cl 0.7075(7) 0.0906(6) 0.0942(4) 0.157(7) Uani 0.723(18) 1 d P C 1 Cl6 Cl 0.6450(9) 0.2692(19) 0.0772(7) 0.103(4) Uani 0.723(18) 1 d PU C 1 C46A C 0.641(4) 0.172(5) 0.095(2) 0.090(9) Uani 0.277(18) 1 d PU C 2 H46C H 0.5880 0.1714 0.0982 0.108 Uiso 0.277(18) 1 calc PR C 2 H46D H 0.6526 0.1205 0.0769 0.108 Uiso 0.277(18) 1 calc PR C 2 Cl5A Cl 0.6765(13) 0.148(3) 0.1375(11) 0.19(2) Uani 0.277(18) 1 d P C 2 Cl6A Cl 0.663(2) 0.272(5) 0.0714(17) 0.098(8) Uani 0.277(18) 1 d PU C 2 C6A C 0.2014(7) 0.5361(10) 0.1476(4) 0.071(5) Uani 0.27(2) 1 d P A 3 H6A1 H 0.2010 0.4871 0.1275 0.085 Uiso 0.27(2) 1 calc PR A 3 H6A2 H 0.1838 0.5934 0.1353 0.085 Uiso 0.27(2) 1 calc PR A 3 C7A C 0.1512(19) 0.509(4) 0.1814(10) 0.063(7) Uani 0.27(2) 1 d PDU A 3 H7A1 H 0.1020 0.4950 0.1724 0.076 Uiso 0.27(2) 1 calc PR A 3 H7A2 H 0.1499 0.5559 0.2024 0.076 Uiso 0.27(2) 1 calc PR A 3 C8A C 0.193(2) 0.422(3) 0.193(2) 0.044(8) Uani 0.27(2) 1 d PDU A 3 H8A1 H 0.2052 0.3852 0.1700 0.053 Uiso 0.27(2) 1 calc PR A 3 H8A2 H 0.1639 0.3840 0.2113 0.053 Uiso 0.27(2) 1 calc PR A 3 C24A C 0.525(3) 0.298(2) 0.2133(13) 0.107(5) Uani 0.42(2) 1 d PDU A 3 H24C H 0.5100 0.2601 0.2357 0.128 Uiso 0.42(2) 1 calc PR A 3 H24D H 0.5780 0.3049 0.2142 0.128 Uiso 0.42(2) 1 calc PR A 3 C25A C 0.5026(18) 0.2521(15) 0.1747(5) 0.069(7) Uani 0.42(2) 1 d PDU A 3 H25C H 0.5302 0.1948 0.1703 0.082 Uiso 0.42(2) 1 calc PR A 3 H25D H 0.4509 0.2373 0.1749 0.082 Uiso 0.42(2) 1 calc PR A 3 C26A C 0.520(2) 0.3242(15) 0.1432(11) 0.095(5) Uani 0.42(2) 1 d PDU A 3 H26C H 0.5722 0.3364 0.1430 0.114 Uiso 0.42(2) 1 calc PR A 3 H26D H 0.5063 0.3001 0.1172 0.114 Uiso 0.42(2) 1 calc PR A 3 N2A N 0.2759(5) 0.5502(7) 0.1616(3) 0.042(2) Uani 0.27(2) 1 d P A 3 N3A N 0.2619(4) 0.4547(6) 0.2140(3) 0.037(2) Uani 0.27(2) 1 d P A 3 N5A N 0.4900(14) 0.3934(15) 0.2159(3) 0.136(6) Uani 1 1 d DU A 3 N6A N 0.4795(13) 0.4137(13) 0.1513(3) 0.124(6) Uani 1 1 d DU A 3 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 0.042(6) 0.038(6) 0.049(7) 0.002(5) 0.011(5) 0.011(5) C2 0.057(7) 0.034(6) 0.052(7) 0.011(5) 0.021(6) 0.005(6) C3 0.071(9) 0.059(8) 0.034(6) 0.008(6) -0.004(6) 0.018(7) C4 0.040(6) 0.055(8) 0.045(7) 0.006(6) -0.010(5) 0.009(6) C5 0.038(6) 0.035(6) 0.041(6) -0.002(5) -0.006(5) 0.003(5) C6 0.049(8) 0.101(13) 0.063(9) 0.020(8) -0.032(7) -0.016(8) C7 0.027(8) 0.082(14) 0.072(13) 0.000(10) -0.003(8) -0.019(9) C8 0.016(6) 0.041(10) 0.081(17) 0.003(9) -0.014(9) -0.009(6) C9 0.018(4) 0.031(5) 0.049(6) -0.002(5) -0.011(4) -0.004(4) C10 0.020(4) 0.034(5) 0.052(6) 0.011(5) -0.010(4) -0.009(4) C11 0.025(5) 0.031(6) 0.061(7) 0.004(5) -0.001(5) -0.004(4) C12 0.038(6) 0.034(6) 0.058(8) 0.005(5) 0.004(5) 0.002(5) C13 0.045(7) 0.041(7) 0.077(9) 0.018(7) -0.001(6) -0.009(6) C14 0.043(7) 0.057(8) 0.063(8) 0.009(7) 0.009(6) -0.017(6) C15 0.022(5) 0.036(6) 0.067(8) 0.004(6) 0.008(5) -0.006(4) C16 0.064(8) 0.026(6) 0.083(10) 0.001(6) 0.025(7) -0.009(6) C17 0.076(10) 0.084(11) 0.055(8) 0.027(8) -0.006(7) -0.020(9) C18 0.043(7) 0.043(7) 0.095(11) 0.001(7) 0.030(7) 0.009(6) C19 0.024(5) 0.071(9) 0.055(7) 0.013(7) -0.006(5) -0.007(5) C20 0.023(5) 0.110(13) 0.051(8) 0.010(8) -0.009(5) -0.010(7) C21 0.039(7) 0.103(13) 0.091(12) 0.046(11) -0.025(8) -0.027(8) C22 0.056(8) 0.061(9) 0.084(11) 0.033(8) -0.039(8) -0.014(7) C23 0.037(6) 0.046(7) 0.051(7) 0.015(6) -0.017(5) -0.016(5) C24 0.104(7) 0.092(7) 0.120(7) -0.001(6) -0.016(6) 0.015(6) C25 0.066(14) 0.052(14) 0.100(16) -0.025(13) -0.021(14) 0.027(11) C26 0.091(8) 0.079(7) 0.109(7) -0.006(6) 0.002(6) 0.010(6) C27 0.029(5) 0.034(6) 0.051(7) 0.003(5) -0.008(5) -0.001(5) C28 0.055(7) 0.030(6) 0.051(7) -0.004(5) 0.015(6) 0.008(5) C29 0.072(10) 0.034(7) 0.107(13) -0.010(8) 0.053(9) 0.001(7) C30 0.150(19) 0.038(8) 0.098(14) -0.014(9) 0.092(14) -0.021(11) C31 0.133(16) 0.032(7) 0.072(11) -0.001(7) 0.056(11) -0.002(9) C32 0.099(12) 0.060(9) 0.044(7) -0.002(7) 0.020(8) 0.034(9) C33 0.052(7) 0.039(6) 0.054(7) -0.006(5) 0.022(6) 0.002(6) C34 0.049(9) 0.074(11) 0.133(16) -0.017(11) 0.043(9) -0.017(8) C35 0.25(3) 0.070(12) 0.053(10) 0.022(9) 0.047(14) 0.036(16) C36 0.050(7) 0.062(9) 0.052(7) 0.003(6) 0.013(6) 0.000(6) C37 0.097(14) 0.130(19) 0.073(12) 0.037(12) -0.042(11) -0.055(13) C38 0.37(5) 0.13(2) 0.032(9) -0.017(11) 0.026(18) 0.02(3) C39 0.27(4) 0.22(3) 0.089(18) 0.030(17) 0.10(2) 0.09(3) C40 0.27(4) 0.21(3) 0.109(19) 0.034(18) 0.10(2) 0.09(3) C41 0.057(11) 0.17(2) 0.17(2) 0.120(19) 0.024(12) -0.004(13) C42 0.055(9) 0.084(12) 0.077(10) 0.019(9) 0.001(8) -0.022(8) C43 0.18(2) 0.050(10) 0.077(12) 0.001(9) -0.019(13) 0.014(12) C44 0.088(15) 0.14(2) 0.14(2) 0.031(17) -0.013(14) 0.009(15) N1 0.032(4) 0.034(5) 0.033(4) 0.000(4) 0.001(4) -0.002(4) N2 0.029(4) 0.049(6) 0.047(5) 0.004(5) -0.020(4) -0.002(4) N3 0.022(4) 0.031(5) 0.057(6) 0.007(4) -0.010(4) -0.008(4) N4 0.021(4) 0.042(5) 0.046(5) 0.012(4) -0.012(4) -0.014(4) N5 0.108(7) 0.105(7) 0.131(7) 0.002(6) -0.019(6) 0.007(6) N6 0.093(7) 0.090(7) 0.120(7) -0.006(6) 0.001(6) 0.008(6) Cl1 0.0336(13) 0.0337(13) 0.0456(14) -0.0075(11) -0.0021(11) -0.0042(11) Cl2 0.0238(11) 0.0360(14) 0.0666(19) 0.0007(13) -0.0053(11) -0.0097(10) Cl3 0.0463(19) 0.156(5) 0.061(2) 0.044(3) -0.0058(17) -0.003(2) Cl4 0.220(7) 0.050(2) 0.106(4) 0.018(3) 0.017(4) -0.035(3) Rh1 0.0207(3) 0.0255(4) 0.0437(4) 0.0022(3) -0.0069(3) -0.0041(3) Rh2 0.0596(7) 0.0567(6) 0.0425(5) 0.0118(5) 0.0190(5) 0.0135(5) C46 0.088(15) 0.077(16) 0.10(2) -0.006(16) -0.018(17) 0.001(13) Cl5 0.176(10) 0.091(6) 0.204(14) 0.034(7) -0.124(10) -0.047(6) Cl6 0.066(7) 0.123(7) 0.119(8) -0.001(6) 0.040(5) 0.014(6) C46A 0.089(17) 0.079(18) 0.10(2) -0.004(19) -0.02(2) 0.001(15) Cl5A 0.098(16) 0.26(4) 0.21(4) 0.17(3) -0.073(19) -0.10(2) Cl6A 0.072(19) 0.117(13) 0.106(17) 0.027(13) 0.013(15) 0.014(16) C6A 0.049(8) 0.101(13) 0.063(9) 0.020(8) -0.032(7) -0.016(8) C7A 0.032(12) 0.083(17) 0.075(15) 0.002(13) -0.007(11) -0.017(12) C8A 0.013(10) 0.041(14) 0.08(2) 0.008(13) -0.015(13) -0.007(10) C24A 0.105(8) 0.095(7) 0.121(7) 0.000(6) -0.015(6) 0.013(6) C25A 0.063(15) 0.047(14) 0.095(17) -0.027(13) -0.030(15) 0.029(12) C26A 0.093(8) 0.083(7) 0.110(7) -0.007(6) 0.002(6) 0.009(6) N2A 0.029(4) 0.049(6) 0.047(5) 0.004(5) -0.020(4) -0.002(4) N3A 0.022(4) 0.031(5) 0.057(6) 0.007(4) -0.010(4) -0.008(4) N5A 0.129(9) 0.128(9) 0.151(8) 0.000(7) -0.021(7) 0.007(7) N6A 0.117(9) 0.112(8) 0.143(8) -0.005(7) 0.002(7) 0.001(7) _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 1.348(14) . ? C1 C2 1.353(16) . ? C2 C3 1.369(18) . ? C3 C4 1.391(18) . ? C4 C5 1.373(15) . ? C5 N1 1.357(13) . ? C5 N2 1.390(14) . ? C6 N2 1.485(14) . ? C6 C7 1.541(5) . ? C7 C8 1.539(5) . ? C8 N3 1.504(17) . ? C9 N3 1.288(13) . ? C9 N2 1.381(13) . ? C9 Rh1 2.029(9) . ? C10 C11 1.402(15) . ? C10 C15 1.412(16) . ? C10 N3 1.449(13) . ? C11 C12 1.381(16) . ? C11 C16 1.503(17) . ? C12 C13 1.398(18) . ? C13 C14 1.394(18) . ? C13 C17 1.482(18) . ? C14 C15 1.379(17) . ? C15 C18 1.509(16) . ? C19 N4 1.313(16) . ? C19 C20 1.373(17) . ? C20 C21 1.42(2) . ? C21 C22 1.34(2) . ? C22 C23 1.359(16) . ? C23 N4 1.295(14) . ? C23 N5 1.544(6) . ? C24 N5 1.532(6) . ? C24 C25 1.540(4) . ? C25 C26 1.539(4) . ? C26 N6 1.529(6) . ? C27 N6 1.377(6) . ? C27 N5 1.381(6) . ? C27 Rh1 1.951(10) . ? C28 C33 1.344(17) . ? C28 C29 1.377(17) . ? C28 N6 1.546(6) . ? C29 C30 1.44(3) . ? C29 C34 1.46(2) . ? C30 C31 1.34(3) . ? C31 C32 1.41(2) . ? C31 C35 1.52(2) . ? C32 C33 1.383(18) . ? C33 C36 1.520(17) . ? C37 C38 1.300(5) . ? C37 C44 1.538(5) . ? C37 Rh2 2.077(15) . ? C38 C39 1.541(5) . ? C38 Rh2 2.123(19) . ? C39 C40 1.539(5) . ? C40 C41 1.537(5) . ? C41 C42 1.299(5) . ? C41 Rh2 2.125(17) . ? C42 C43 1.535(5) . ? C42 Rh2 2.097(15) . ? C43 C44 1.536(5) . ? N1 Rh1 2.031(8) . ? N4 Rh1 2.038(9) . ? Cl1 Rh1 2.412(3) . ? Cl2 Rh1 2.418(2) . ? Cl3 Rh2 2.398(4) . ? Cl4 Rh2 2.359(5) . ? C46 Cl6 1.75(4) . ? C46 Cl5 1.75(3) . ? C46A Cl5A 1.64(7) . ? C46A Cl6A 1.71(10) . ? C7A C8A 1.540(5) . ? C24A N5A 1.531(6) . ? C24A C25A 1.539(6) . ? C25A C26A 1.538(6) . ? C26A N6A 1.530(6) . ? 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 C2 123.1(12) . . ? C1 C2 C3 119.3(12) . . ? C2 C3 C4 119.4(11) . . ? C5 C4 C3 118.2(11) . . ? N1 C5 C4 122.3(11) . . ? N1 C5 N2 113.7(9) . . ? C4 C5 N2 124.0(10) . . ? N2 C6 C7 109.1(10) . . ? C8 C7 C6 107.0(14) . . ? N3 C8 C7 106.2(12) . . ? N3 C9 N2 117.5(8) . . ? N3 C9 Rh1 131.4(8) . . ? N2 C9 Rh1 111.0(7) . . ? C11 C10 C15 120.9(10) . . ? C11 C10 N3 120.6(11) . . ? C15 C10 N3 118.1(10) . . ? C12 C11 C10 119.0(11) . . ? C12 C11 C16 119.2(10) . . ? C10 C11 C16 121.8(11) . . ? C11 C12 C13 121.4(11) . . ? C14 C13 C12 117.9(12) . . ? C14 C13 C17 122.0(14) . . ? C12 C13 C17 120.0(13) . . ? C15 C14 C13 122.9(13) . . ? C14 C15 C10 117.6(11) . . ? C14 C15 C18 120.4(12) . . ? C10 C15 C18 122.0(11) . . ? N4 C19 C20 123.5(13) . . ? C19 C20 C21 117.1(14) . . ? C22 C21 C20 120.0(14) . . ? C21 C22 C23 114.9(15) . . ? N4 C23 C22 129.4(12) . . ? N4 C23 N5 109.7(9) . . ? C22 C23 N5 120.8(12) . . ? N5 C24 C25 109.9(18) . . ? C26 C25 C24 114.6(15) . . ? N6 C26 C25 106.9(16) . . ? N6 C27 N5 111.1(9) . . ? N6 C27 Rh1 131.9(7) . . ? N5 C27 Rh1 115.4(7) . . ? C33 C28 C29 128.2(12) . . ? C33 C28 N6 109.3(13) . . ? C29 C28 N6 122.2(16) . . ? C28 C29 C30 110.8(16) . . ? C28 C29 C34 124.3(16) . . ? C30 C29 C34 124.7(15) . . ? C31 C30 C29 124.6(15) . . ? C30 C31 C32 119.3(17) . . ? C30 C31 C35 118.7(18) . . ? C32 C31 C35 122(2) . . ? C33 C32 C31 119.1(17) . . ? C28 C33 C32 117.7(12) . . ? C28 C33 C36 124.2(12) . . ? C32 C33 C36 118.1(13) . . ? C38 C37 C44 125(2) . . ? C38 C37 Rh2 73.9(11) . . ? C44 C37 Rh2 112.9(12) . . ? C37 C38 C39 125(2) . . ? C37 C38 Rh2 70.1(10) . . ? C39 C38 Rh2 109.2(16) . . ? C40 C39 C38 120(2) . . ? C41 C40 C39 110(2) . . ? C42 C41 C40 128(2) . . ? C42 C41 Rh2 70.9(9) . . ? C40 C41 Rh2 113.7(17) . . ? C41 C42 C43 124.8(17) . . ? C41 C42 Rh2 73.2(10) . . ? C43 C42 Rh2 112.8(10) . . ? C42 C43 C44 114.2(13) . . ? C43 C44 C37 113.4(14) . . ? C1 N1 C5 117.4(9) . . ? C1 N1 Rh1 125.9(8) . . ? C5 N1 Rh1 114.7(7) . . ? C9 N2 C5 119.6(8) . . ? C9 N2 C6 123.7(9) . . ? C5 N2 C6 116.6(9) . . ? C9 N3 C10 125.0(8) . . ? C9 N3 C8 126.1(11) . . ? C10 N3 C8 108.4(10) . . ? C23 N4 C19 115.1(9) . . ? C23 N4 Rh1 118.5(7) . . ? C19 N4 Rh1 125.2(8) . . ? C27 N5 C24 126.7(16) . . ? C27 N5 C23 113.9(9) . . ? C24 N5 C23 113.2(11) . . ? C27 N6 C26 129.0(12) . . ? C27 N6 C28 121.1(10) . . ? C26 N6 C28 105.3(10) . . ? C27 Rh1 C9 96.3(4) . . ? C27 Rh1 N1 102.9(3) . . ? C9 Rh1 N1 80.4(4) . . ? C27 Rh1 N4 80.1(4) . . ? C9 Rh1 N4 102.5(4) . . ? N1 Rh1 N4 175.6(4) . . ? C27 Rh1 Cl1 174.1(3) . . ? C9 Rh1 Cl1 86.3(3) . . ? N1 Rh1 Cl1 82.7(2) . . ? N4 Rh1 Cl1 94.2(3) . . ? C27 Rh1 Cl2 85.9(3) . . ? C9 Rh1 Cl2 175.1(3) . . ? N1 Rh1 Cl2 94.9(2) . . ? N4 Rh1 Cl2 82.1(2) . . ? Cl1 Rh1 Cl2 91.95(9) . . ? C37 Rh2 C42 83.6(6) . . ? C37 Rh2 C38 36.0(3) . . ? C42 Rh2 C38 93.4(8) . . ? C37 Rh2 C41 95.6(7) . . ? C42 Rh2 C41 35.8(2) . . ? C38 Rh2 C41 83.6(8) . . ? C37 Rh2 Cl4 89.2(5) . . ? C42 Rh2 Cl4 162.8(4) . . ? C38 Rh2 Cl4 89.8(7) . . ? C41 Rh2 Cl4 161.3(5) . . ? C37 Rh2 Cl3 160.9(6) . . ? C42 Rh2 Cl3 89.5(4) . . ? C38 Rh2 Cl3 162.9(7) . . ? C41 Rh2 Cl3 88.9(6) . . ? Cl4 Rh2 Cl3 92.4(2) . . ? Cl6 C46 Cl5 112.4(17) . . ? Cl5A C46A Cl6A 120(5) . . ? N5A C24A C25A 109.2(18) . . ? C26A C25A C24A 104(4) . . ? N6A C26A C25A 110.5(17) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.220 _refine_diff_density_min -1.448 _refine_diff_density_rms 0.174 # Attachment 'kjc0846.cif' data_kjc0846 _database_code_depnum_ccdc_archive 'CCDC 733105' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C31 H42 Cl Ir N2 O' _chemical_formula_sum 'C31 H42 Cl Ir N2 O' _chemical_formula_weight 686.32 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 0.0000 0.0000 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Ir Ir -1.4442 7.9887 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 17.4350(3) _cell_length_b 10.4170(2) _cell_length_c 17.6770(4) _cell_angle_alpha 90.00 _cell_angle_beta 116.7360(10) _cell_angle_gamma 90.00 _cell_volume 2867.26(10) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5700 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 27.46 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.590 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1376 _exptl_absorpt_coefficient_mu 4.776 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.4485 _exptl_absorpt_correction_T_max 0.4802 _exptl_absorpt_process_details Denzo/Scalepack _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'CCD scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10761 _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_sigmaI/netI 0.0483 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 27.46 _reflns_number_total 6537 _reflns_number_gt 5700 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'cOLLECT,Nonius BV, 1997-2001' _computing_cell_refinement DENZO/SCALEPACK _computing_data_reduction DENZO/SCALEPACK _computing_structure_solution SHELXs-97 _computing_structure_refinement SHELXL-97 _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^)+(0.0000P)^2^+4.9239P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6537 _refine_ls_number_parameters 330 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0349 _refine_ls_R_factor_gt 0.0279 _refine_ls_wR_factor_ref 0.0611 _refine_ls_wR_factor_gt 0.0583 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5659(2) 0.1869(3) 0.77060(19) 0.0108(7) Uani 1 1 d . . . C2 C 0.6458(2) 0.3707(3) 0.7513(3) 0.0234(9) Uani 1 1 d . . . H2A H 0.6971 0.3832 0.8063 0.028 Uiso 1 1 calc R . . H2B H 0.6280 0.4554 0.7234 0.028 Uiso 1 1 calc R . . C3 C 0.6667(3) 0.2813(4) 0.6962(2) 0.0229(8) Uani 1 1 d . . . H3A H 0.7150 0.3162 0.6876 0.027 Uiso 1 1 calc R . . H3B H 0.6163 0.2724 0.6401 0.027 Uiso 1 1 calc R . . C4 C 0.6908(2) 0.1516(3) 0.7395(2) 0.0201(8) Uani 1 1 d . . . H4A H 0.6965 0.0880 0.7006 0.024 Uiso 1 1 calc R . . H4B H 0.7468 0.1579 0.7906 0.024 Uiso 1 1 calc R . . C5 C 0.5231(2) 0.4023(3) 0.7835(2) 0.0124(7) Uani 1 1 d . . . C6 C 0.5526(2) 0.4459(3) 0.8665(2) 0.0167(7) Uani 1 1 d . . . C7 C 0.5024(2) 0.5288(3) 0.8873(2) 0.0186(8) Uani 1 1 d . . . H7 H 0.5212 0.5562 0.9442 0.022 Uiso 1 1 calc R . . C8 C 0.4238(2) 0.5712(3) 0.8232(2) 0.0200(8) Uani 1 1 d . . . H8 H 0.3892 0.6280 0.8367 0.024 Uiso 1 1 calc R . . C9 C 0.3962(2) 0.5313(4) 0.7406(2) 0.0211(8) Uani 1 1 d . . . H9 H 0.3429 0.5613 0.6975 0.025 Uiso 1 1 calc R . . C10 C 0.4459(2) 0.4475(3) 0.7202(2) 0.0175(7) Uani 1 1 d . . . H10 H 0.4273 0.4212 0.6631 0.021 Uiso 1 1 calc R . . C11 C 0.6630(3) 0.4384(5) 1.0095(2) 0.0328(10) Uani 1 1 d . . . H11A H 0.6655 0.5323 1.0137 0.049 Uiso 1 1 calc R . . H11B H 0.7206 0.4028 1.0427 0.049 Uiso 1 1 calc R . . H11C H 0.6243 0.4056 1.0315 0.049 Uiso 1 1 calc R . . C12 C 0.6343(2) -0.0222(3) 0.7940(2) 0.0141(7) Uani 1 1 d . . . C13 C 0.5900(2) -0.1228(3) 0.7388(2) 0.0173(7) Uani 1 1 d . . . C14 C 0.6022(2) -0.2467(3) 0.7723(2) 0.0209(8) Uani 1 1 d . . . H14 H 0.5721 -0.3162 0.7363 0.025 Uiso 1 1 calc R . . C15 C 0.6569(2) -0.2709(3) 0.8565(2) 0.0205(8) Uani 1 1 d . . . H15 H 0.6636 -0.3559 0.8780 0.025 Uiso 1 1 calc R . . C16 C 0.7021(2) -0.1701(3) 0.9095(2) 0.0184(8) Uani 1 1 d . . . H16 H 0.7408 -0.1873 0.9669 0.022 Uiso 1 1 calc R . . C17 C 0.6917(2) -0.0447(3) 0.8798(2) 0.0139(7) Uani 1 1 d . . . C18 C 0.5327(2) -0.1019(4) 0.6447(2) 0.0246(9) Uani 1 1 d . . . H18 H 0.5227 -0.0075 0.6349 0.029 Uiso 1 1 calc R . . C19 C 0.5780(3) -0.1489(5) 0.5930(3) 0.0438(13) Uani 1 1 d . . . H19A H 0.6328 -0.1038 0.6115 0.066 Uiso 1 1 calc R . . H19B H 0.5416 -0.1317 0.5328 0.066 Uiso 1 1 calc R . . H19C H 0.5885 -0.2415 0.6015 0.066 Uiso 1 1 calc R . . C20 C 0.4453(3) -0.1672(4) 0.6150(3) 0.0400(12) Uani 1 1 d . . . H20A H 0.4532 -0.2605 0.6205 0.060 Uiso 1 1 calc R . . H20B H 0.4086 -0.1451 0.5556 0.060 Uiso 1 1 calc R . . H20C H 0.4182 -0.1378 0.6499 0.060 Uiso 1 1 calc R . . C21 C 0.7455(2) 0.0613(3) 0.9393(2) 0.0169(7) Uani 1 1 d . . . H21 H 0.7283 0.1447 0.9081 0.020 Uiso 1 1 calc R . . C22 C 0.7310(2) 0.0718(4) 1.0189(2) 0.0218(8) Uani 1 1 d . . . H22A H 0.6709 0.0939 1.0021 0.033 Uiso 1 1 calc R . . H22B H 0.7685 0.1387 1.0563 0.033 Uiso 1 1 calc R . . H22C H 0.7445 -0.0107 1.0488 0.033 Uiso 1 1 calc R . . C23 C 0.8418(2) 0.0403(4) 0.9663(2) 0.0214(8) Uani 1 1 d . . . H23A H 0.8609 -0.0383 1.0001 0.032 Uiso 1 1 calc R . . H23B H 0.8745 0.1136 1.0001 0.032 Uiso 1 1 calc R . . H23C H 0.8510 0.0322 0.9158 0.032 Uiso 1 1 calc R . . C24 C 0.4973(2) 0.0248(3) 0.8786(2) 0.0131(7) Uani 1 1 d . . . H24 H 0.5467 0.0078 0.8706 0.016 Uiso 1 1 calc R . . C25 C 0.4832(2) 0.1538(3) 0.8946(2) 0.0147(7) Uani 1 1 d . . . H25 H 0.5224 0.2177 0.8953 0.018 Uiso 1 1 calc R . . C26 C 0.4078(2) 0.1945(4) 0.9108(2) 0.0250(9) Uani 1 1 d . . . H26A H 0.3944 0.1242 0.9407 0.030 Uiso 1 1 calc R . . H26B H 0.4250 0.2705 0.9485 0.030 Uiso 1 1 calc R . . C27 C 0.3285(2) 0.2267(5) 0.8316(2) 0.0310(10) Uani 1 1 d . . . H27A H 0.3268 0.3205 0.8223 0.037 Uiso 1 1 calc R . . H27B H 0.2776 0.2036 0.8397 0.037 Uiso 1 1 calc R . . C28 C 0.3225(2) 0.1587(4) 0.7528(2) 0.0184(8) Uani 1 1 d . . . H28 H 0.3110 0.2110 0.7049 0.022 Uiso 1 1 calc R . . C29 C 0.3322(2) 0.0283(4) 0.7440(2) 0.0174(8) Uani 1 1 d . . . H29 H 0.3292 -0.0020 0.6921 0.021 Uiso 1 1 calc R . . C30 C 0.3472(2) -0.0677(4) 0.8133(3) 0.0311(10) Uani 1 1 d . . . H30A H 0.3170 -0.0381 0.8461 0.037 Uiso 1 1 calc R . . H30B H 0.3219 -0.1511 0.7872 0.037 Uiso 1 1 calc R . . C31 C 0.4407(2) -0.0872(4) 0.8732(2) 0.0246(9) Uani 1 1 d . . . H31A H 0.4462 -0.1049 0.9305 0.030 Uiso 1 1 calc R . . H31B H 0.4616 -0.1639 0.8549 0.030 Uiso 1 1 calc R . . N1 N 0.57595(17) 0.3140(3) 0.76475(18) 0.0130(6) Uani 1 1 d . . . N2 N 0.62410(17) 0.1089(3) 0.76372(17) 0.0122(6) Uani 1 1 d . . . O1 O 0.63190(15) 0.4014(3) 0.92321(15) 0.0205(6) Uani 1 1 d . . . Cl1 Cl 0.39577(5) 0.15898(8) 0.61540(5) 0.01629(17) Uani 1 1 d . . . Ir1 Ir 0.450242(7) 0.129114(12) 0.764543(7) 0.01001(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0102(15) 0.0134(16) 0.0066(15) -0.0004(13) 0.0017(13) 0.0013(13) C2 0.026(2) 0.0136(18) 0.043(2) 0.0025(17) 0.0264(19) -0.0019(15) C3 0.031(2) 0.0213(19) 0.032(2) 0.0071(17) 0.0273(18) 0.0023(17) C4 0.0213(18) 0.0179(18) 0.030(2) 0.0033(16) 0.0194(17) -0.0005(15) C5 0.0135(16) 0.0092(15) 0.0173(16) 0.0023(14) 0.0093(14) 0.0003(13) C6 0.0142(17) 0.0157(18) 0.0210(18) -0.0020(15) 0.0087(15) -0.0021(14) C7 0.0222(19) 0.0145(18) 0.0193(18) -0.0073(15) 0.0093(16) -0.0037(15) C8 0.0182(18) 0.0112(17) 0.032(2) -0.0019(16) 0.0131(17) 0.0029(15) C9 0.0125(17) 0.0167(18) 0.028(2) 0.0012(16) 0.0037(16) 0.0021(15) C10 0.0195(18) 0.0139(17) 0.0171(17) -0.0034(15) 0.0065(15) -0.0015(15) C11 0.025(2) 0.050(3) 0.0148(19) -0.0036(19) 0.0012(17) 0.008(2) C12 0.0145(16) 0.0129(16) 0.0197(18) -0.0004(14) 0.0121(15) -0.0001(14) C13 0.0144(17) 0.0179(18) 0.0225(18) -0.0054(15) 0.0109(15) 0.0013(14) C14 0.0200(18) 0.0124(18) 0.033(2) -0.0048(16) 0.0140(17) -0.0032(15) C15 0.0200(18) 0.0122(17) 0.034(2) 0.0050(16) 0.0164(17) -0.0008(15) C16 0.0207(18) 0.0182(18) 0.0193(18) 0.0037(15) 0.0118(16) 0.0036(15) C17 0.0146(16) 0.0162(17) 0.0154(17) 0.0028(14) 0.0108(14) 0.0020(14) C18 0.026(2) 0.022(2) 0.0203(19) -0.0050(16) 0.0053(17) 0.0055(17) C19 0.049(3) 0.055(3) 0.024(2) -0.008(2) 0.014(2) 0.022(2) C20 0.029(2) 0.027(2) 0.041(3) -0.010(2) -0.006(2) -0.003(2) C21 0.0183(17) 0.0172(18) 0.0149(17) 0.0009(14) 0.0072(15) -0.0013(15) C22 0.0151(17) 0.031(2) 0.0161(18) -0.0049(16) 0.0043(15) -0.0040(16) C23 0.0202(18) 0.024(2) 0.0229(19) -0.0035(16) 0.0119(16) -0.0053(16) C24 0.0124(16) 0.0176(17) 0.0095(15) 0.0022(14) 0.0051(14) -0.0005(14) C25 0.0160(17) 0.0188(18) 0.0124(16) 0.0001(14) 0.0091(14) -0.0007(14) C26 0.0182(18) 0.038(2) 0.0185(19) -0.0067(17) 0.0080(16) 0.0067(17) C27 0.0183(19) 0.047(3) 0.030(2) -0.004(2) 0.0121(18) 0.0082(19) C28 0.0071(16) 0.029(2) 0.0181(18) 0.0021(16) 0.0052(14) -0.0004(15) C29 0.0092(16) 0.025(2) 0.0157(17) 0.0015(15) 0.0036(14) -0.0061(15) C30 0.021(2) 0.034(2) 0.029(2) 0.0121(19) 0.0034(18) -0.0107(18) C31 0.0215(19) 0.024(2) 0.024(2) 0.0091(17) 0.0069(17) -0.0058(17) N1 0.0119(13) 0.0123(14) 0.0170(14) -0.0018(12) 0.0085(12) -0.0010(12) N2 0.0109(13) 0.0150(14) 0.0139(14) 0.0010(12) 0.0084(12) 0.0004(11) O1 0.0121(12) 0.0302(15) 0.0138(12) -0.0030(11) 0.0010(10) 0.0038(11) Cl1 0.0168(4) 0.0192(4) 0.0109(4) 0.0014(3) 0.0046(3) 0.0014(3) Ir1 0.00881(7) 0.01070(8) 0.01011(7) 0.00048(5) 0.00388(6) -0.00034(5) _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 1.346(4) . ? C1 N2 1.348(4) . ? C1 Ir1 2.060(3) . ? C2 N1 1.467(4) . ? C2 C3 1.506(5) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.516(5) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 N2 1.478(4) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C10 1.391(5) . ? C5 C6 1.393(5) . ? C5 N1 1.442(4) . ? C6 O1 1.373(4) . ? C6 C7 1.393(5) . ? C7 C8 1.400(5) . ? C7 H7 0.9500 . ? C8 C9 1.380(5) . ? C8 H8 0.9500 . ? C9 C10 1.387(5) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 O1 1.423(4) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.403(5) . ? C12 C17 1.410(5) . ? C12 N2 1.449(4) . ? C13 C14 1.396(5) . ? C13 C18 1.522(5) . ? C14 C15 1.382(5) . ? C14 H14 0.9500 . ? C15 C16 1.392(5) . ? C15 H15 0.9500 . ? C16 C17 1.389(5) . ? C16 H16 0.9500 . ? C17 C21 1.523(5) . ? C18 C20 1.530(6) . ? C18 C19 1.533(6) . ? C18 H18 1.0000 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C23 1.539(5) . ? C21 C22 1.542(5) . ? C21 H21 1.0000 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C24 C25 1.417(5) . ? C24 C31 1.503(5) . ? C24 Ir1 2.104(3) . ? C24 H24 0.9500 . ? C25 C26 1.525(5) . ? C25 Ir1 2.120(3) . ? C25 H25 0.9500 . ? C26 C27 1.498(5) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.524(5) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 C29 1.386(5) . ? C28 Ir1 2.164(3) . ? C28 H28 0.9500 . ? C29 C30 1.511(5) . ? C29 Ir1 2.191(3) . ? C29 H29 0.9500 . ? C30 C31 1.505(5) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? Cl1 Ir1 2.3867(8) . ? 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 117.2(3) . . ? N1 C1 Ir1 116.2(2) . . ? N2 C1 Ir1 125.4(2) . . ? N1 C2 C3 108.4(3) . . ? N1 C2 H2A 110.0 . . ? C3 C2 H2A 110.0 . . ? N1 C2 H2B 110.0 . . ? C3 C2 H2B 110.0 . . ? H2A C2 H2B 108.4 . . ? C2 C3 C4 108.5(3) . . ? C2 C3 H3A 110.0 . . ? C4 C3 H3A 110.0 . . ? C2 C3 H3B 110.0 . . ? C4 C3 H3B 110.0 . . ? H3A C3 H3B 108.4 . . ? N2 C4 C3 109.8(3) . . ? N2 C4 H4A 109.7 . . ? C3 C4 H4A 109.7 . . ? N2 C4 H4B 109.7 . . ? C3 C4 H4B 109.7 . . ? H4A C4 H4B 108.2 . . ? C10 C5 C6 120.1(3) . . ? C10 C5 N1 121.2(3) . . ? C6 C5 N1 118.6(3) . . ? O1 C6 C7 124.2(3) . . ? O1 C6 C5 115.6(3) . . ? C7 C6 C5 120.2(3) . . ? C6 C7 C8 118.9(3) . . ? C6 C7 H7 120.6 . . ? C8 C7 H7 120.6 . . ? C9 C8 C7 120.8(3) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C8 C9 C10 120.2(3) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C9 C10 C5 119.7(3) . . ? C9 C10 H10 120.1 . . ? C5 C10 H10 120.1 . . ? O1 C11 H11A 109.5 . . ? O1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 C17 121.8(3) . . ? C13 C12 N2 120.6(3) . . ? C17 C12 N2 117.6(3) . . ? C14 C13 C12 117.7(3) . . ? C14 C13 C18 119.7(3) . . ? C12 C13 C18 122.6(3) . . ? C15 C14 C13 121.6(3) . . ? C15 C14 H14 119.2 . . ? C13 C14 H14 119.2 . . ? C14 C15 C16 119.7(3) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? C17 C16 C15 121.1(3) . . ? C17 C16 H16 119.4 . . ? C15 C16 H16 119.4 . . ? C16 C17 C12 118.1(3) . . ? C16 C17 C21 119.1(3) . . ? C12 C17 C21 122.8(3) . . ? C13 C18 C20 112.0(3) . . ? C13 C18 C19 110.2(3) . . ? C20 C18 C19 110.7(4) . . ? C13 C18 H18 108.0 . . ? C20 C18 H18 108.0 . . ? C19 C18 H18 108.0 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C17 C21 C23 111.0(3) . . ? C17 C21 C22 112.2(3) . . ? C23 C21 C22 109.3(3) . . ? C17 C21 H21 108.1 . . ? C23 C21 H21 108.1 . . ? C22 C21 H21 108.1 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C25 C24 C31 125.5(3) . . ? C25 C24 Ir1 70.99(19) . . ? C31 C24 Ir1 112.2(2) . . ? C25 C24 H24 117.3 . . ? C31 C24 H24 117.3 . . ? Ir1 C24 H24 86.7 . . ? C24 C25 C26 122.9(3) . . ? C24 C25 Ir1 69.82(18) . . ? C26 C25 Ir1 113.7(2) . . ? C24 C25 H25 118.6 . . ? C26 C25 H25 118.6 . . ? Ir1 C25 H25 86.6 . . ? C27 C26 C25 113.5(3) . . ? C27 C26 H26A 108.9 . . ? C25 C26 H26A 108.9 . . ? C27 C26 H26B 108.9 . . ? C25 C26 H26B 108.9 . . ? H26A C26 H26B 107.7 . . ? C26 C27 C28 113.9(3) . . ? C26 C27 H27A 108.8 . . ? C28 C27 H27A 108.8 . . ? C26 C27 H27B 108.8 . . ? C28 C27 H27B 108.8 . . ? H27A C27 H27B 107.7 . . ? C29 C28 C27 126.6(4) . . ? C29 C28 Ir1 72.5(2) . . ? C27 C28 Ir1 109.6(2) . . ? C29 C28 H28 116.7 . . ? C27 C28 H28 116.7 . . ? Ir1 C28 H28 87.8 . . ? C28 C29 C30 122.9(4) . . ? C28 C29 Ir1 70.40(19) . . ? C30 C29 Ir1 112.1(2) . . ? C28 C29 H29 118.5 . . ? C30 C29 H29 118.5 . . ? Ir1 C29 H29 87.6 . . ? C31 C30 C29 113.4(3) . . ? C31 C30 H30A 108.9 . . ? C29 C30 H30A 108.9 . . ? C31 C30 H30B 108.9 . . ? C29 C30 H30B 108.9 . . ? H30A C30 H30B 107.7 . . ? C24 C31 C30 114.3(3) . . ? C24 C31 H31A 108.7 . . ? C30 C31 H31A 108.7 . . ? C24 C31 H31B 108.7 . . ? C30 C31 H31B 108.7 . . ? H31A C31 H31B 107.6 . . ? C1 N1 C5 119.4(3) . . ? C1 N1 C2 123.8(3) . . ? C5 N1 C2 116.3(3) . . ? C1 N2 C12 120.5(3) . . ? C1 N2 C4 124.6(3) . . ? C12 N2 C4 114.1(3) . . ? C6 O1 C11 117.7(3) . . ? C1 Ir1 C24 98.65(13) . . ? C1 Ir1 C25 97.30(13) . . ? C24 Ir1 C25 39.19(13) . . ? C1 Ir1 C28 154.75(14) . . ? C24 Ir1 C28 96.08(14) . . ? C25 Ir1 C28 81.46(13) . . ? C1 Ir1 C29 166.73(14) . . ? C24 Ir1 C29 80.99(13) . . ? C25 Ir1 C29 90.76(13) . . ? C28 Ir1 C29 37.10(14) . . ? C1 Ir1 Cl1 85.02(9) . . ? C24 Ir1 Cl1 156.26(10) . . ? C25 Ir1 Cl1 163.99(10) . . ? C28 Ir1 Cl1 89.70(10) . . ? C29 Ir1 Cl1 90.14(9) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.854 _refine_diff_density_min -1.185 _refine_diff_density_rms 0.134 # Attachment 'kjc0903.cif' data_kjc0903 _database_code_depnum_ccdc_archive 'CCDC 733106' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H36 Cl Ir N2 O, C4 H8 O' _chemical_formula_sum 'C32 H44 Cl Ir N2 O2' _chemical_formula_weight 716.34 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 0.0000 0.0000 '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' Ir Ir -1.4442 7.9887 '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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.6970(5) _cell_length_b 11.1510(6) _cell_length_c 13.9060(11) _cell_angle_alpha 85.593(2) _cell_angle_beta 79.370(2) _cell_angle_gamma 81.103(4) _cell_volume 1458.28(16) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5422 _cell_measurement_theta_min 1.49 _cell_measurement_theta_max 27.50 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.631 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 720 _exptl_absorpt_coefficient_mu 4.701 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5390 _exptl_absorpt_correction_T_max 0.9118 _exptl_absorpt_process_details Denzo/Scalepack _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'CCD scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9737 _diffrn_reflns_av_R_equivalents 0.0517 _diffrn_reflns_av_sigmaI/netI 0.0964 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.49 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6473 _reflns_number_gt 5422 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'cOLLECT,Nonius BV, 1997-2001' _computing_cell_refinement DENZO/SCALEPACK _computing_data_reduction DENZO/SCALEPACK _computing_structure_solution SHELXs-97 _computing_structure_refinement SHELXL-97 _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^)+(0.0242P)^2^+1.1792P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6473 _refine_ls_number_parameters 347 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0645 _refine_ls_R_factor_gt 0.0481 _refine_ls_wR_factor_ref 0.1008 _refine_ls_wR_factor_gt 0.0946 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6650(6) 0.3041(5) 0.7199(4) 0.0174(12) Uani 1 1 d . . . C2 C 0.4721(6) 0.1793(6) 0.7246(5) 0.0309(16) Uani 1 1 d . . . H2A H 0.3855 0.2250 0.7618 0.037 Uiso 1 1 calc R . . H2B H 0.4665 0.0913 0.7362 0.037 Uiso 1 1 calc R . . C3 C 0.4839(8) 0.2144(6) 0.6164(6) 0.0352(17) Uani 1 1 d . . . H3A H 0.5671 0.1647 0.5790 0.042 Uiso 1 1 calc R . . H3B H 0.3979 0.1996 0.5930 0.042 Uiso 1 1 calc R . . C4 C 0.4999(7) 0.3468(5) 0.6007(5) 0.0286(15) Uani 1 1 d . . . H4A H 0.5240 0.3674 0.5296 0.034 Uiso 1 1 calc R . . H4B H 0.4089 0.3968 0.6265 0.034 Uiso 1 1 calc R . . C5 C 0.6420(6) 0.1391(5) 0.8420(5) 0.0217(13) Uani 1 1 d . . . C6 C 0.5642(6) 0.1737(5) 0.9347(5) 0.0273(15) Uani 1 1 d . . . C7 C 0.6007(7) 0.1098(6) 1.0178(5) 0.0300(15) Uani 1 1 d . . . H7 H 0.5512 0.1326 1.0808 0.036 Uiso 1 1 calc R . . C8 C 0.7094(7) 0.0125(6) 1.0093(6) 0.0344(17) Uani 1 1 d . . . H8 H 0.7349 -0.0304 1.0666 0.041 Uiso 1 1 calc R . . C9 C 0.7805(7) -0.0223(6) 0.9188(6) 0.0339(16) Uani 1 1 d . . . H9 H 0.8531 -0.0905 0.9139 0.041 Uiso 1 1 calc R . . C10 C 0.7469(6) 0.0419(6) 0.8334(5) 0.0278(15) Uani 1 1 d . . . H10 H 0.7964 0.0181 0.7707 0.033 Uiso 1 1 calc R . . C11 C 0.3872(8) 0.3152(7) 1.0253(6) 0.047(2) Uani 1 1 d . . . H11A H 0.3469 0.2494 1.0664 0.070 Uiso 1 1 calc R . . H11B H 0.3110 0.3810 1.0148 0.070 Uiso 1 1 calc R . . H11C H 0.4549 0.3462 1.0579 0.070 Uiso 1 1 calc R . . C12 C 0.6432(6) 0.4993(5) 0.6324(5) 0.0229(14) Uani 1 1 d . . . C13 C 0.5606(6) 0.5869(5) 0.6922(5) 0.0215(13) Uani 1 1 d . . . C14 C 0.5899(6) 0.7064(5) 0.6776(5) 0.0252(14) Uani 1 1 d . . . H14 H 0.5345 0.7667 0.7188 0.030 Uiso 1 1 calc R . . C15 C 0.6982(7) 0.7397(5) 0.6042(5) 0.0278(15) Uani 1 1 d . . . C16 C 0.7731(6) 0.6501(5) 0.5432(5) 0.0246(14) Uani 1 1 d . . . H16 H 0.8461 0.6716 0.4922 0.030 Uiso 1 1 calc R . . C17 C 0.7465(6) 0.5298(5) 0.5532(5) 0.0239(14) Uani 1 1 d . . . C18 C 0.4460(7) 0.5547(6) 0.7758(6) 0.0339(16) Uani 1 1 d . . . H18A H 0.3766 0.5167 0.7501 0.051 Uiso 1 1 calc R . . H18B H 0.3985 0.6287 0.8083 0.051 Uiso 1 1 calc R . . H18C H 0.4889 0.4979 0.8230 0.051 Uiso 1 1 calc R . . C19 C 0.7310(8) 0.8690(6) 0.5922(6) 0.0403(18) Uani 1 1 d . . . H19A H 0.8324 0.8686 0.5673 0.061 Uiso 1 1 calc R . . H19B H 0.7058 0.9064 0.6558 0.061 Uiso 1 1 calc R . . H19C H 0.6759 0.9156 0.5459 0.061 Uiso 1 1 calc R . . C20 C 0.8271(7) 0.4378(5) 0.4828(5) 0.0307(15) Uani 1 1 d . . . H20A H 0.7663 0.4217 0.4376 0.046 Uiso 1 1 calc R . . H20B H 0.8565 0.3623 0.5192 0.046 Uiso 1 1 calc R . . H20C H 0.9111 0.4693 0.4455 0.046 Uiso 1 1 calc R . . C21 C 0.8111(6) 0.4794(5) 0.8217(5) 0.0255(14) Uani 1 1 d . . . H21 H 0.7412 0.4979 0.7810 0.031 Uiso 1 1 calc R . . C22 C 0.7928(7) 0.3844(6) 0.8952(5) 0.0288(15) Uani 1 1 d . . . H22 H 0.7136 0.3423 0.9001 0.035 Uiso 1 1 calc R . . C23 C 0.8959(8) 0.3480(6) 0.9663(5) 0.0342(16) Uani 1 1 d . . . H23A H 0.8433 0.3211 1.0303 0.041 Uiso 1 1 calc R . . H23B H 0.9395 0.4195 0.9766 0.041 Uiso 1 1 calc R . . C24 C 1.0133(8) 0.2449(6) 0.9279(6) 0.0365(17) Uani 1 1 d . . . H24A H 1.0995 0.2513 0.9546 0.044 Uiso 1 1 calc R . . H24B H 0.9822 0.1658 0.9520 0.044 Uiso 1 1 calc R . . C25 C 1.0493(7) 0.2478(6) 0.8181(5) 0.0335(16) Uani 1 1 d . . . H25 H 1.0546 0.1736 0.7874 0.040 Uiso 1 1 calc R . . C26 C 1.0758(6) 0.3507(6) 0.7570(5) 0.0315(16) Uani 1 1 d . . . H26 H 1.0951 0.3423 0.6881 0.038 Uiso 1 1 calc R . . C27 C 1.0753(7) 0.4747(6) 0.7951(6) 0.0337(17) Uani 1 1 d . . . H27A H 1.1032 0.4639 0.8605 0.040 Uiso 1 1 calc R . . H27B H 1.1467 0.5169 0.7507 0.040 Uiso 1 1 calc R . . C28 C 0.9322(6) 0.5536(5) 0.8029(5) 0.0287(15) Uani 1 1 d . . . H28A H 0.9210 0.6092 0.8568 0.034 Uiso 1 1 calc R . . H28B H 0.9283 0.6038 0.7413 0.034 Uiso 1 1 calc R . . C29 C 1.1652(9) -0.1206(8) 0.7889(6) 0.051(2) Uani 1 1 d . . . H29A H 1.0944 -0.0580 0.8241 0.061 Uiso 1 1 calc R . . H29B H 1.1859 -0.1896 0.8358 0.061 Uiso 1 1 calc R . . C30 C 1.1083(9) -0.1633(8) 0.7055(7) 0.058(2) Uani 1 1 d . . . H30A H 1.0152 -0.1156 0.6990 0.070 Uiso 1 1 calc R . . H30B H 1.0971 -0.2504 0.7162 0.070 Uiso 1 1 calc R . . C31 C 1.2180(9) -0.1433(7) 0.6148(7) 0.049(2) Uani 1 1 d . . . H31A H 1.2838 -0.2189 0.5982 0.059 Uiso 1 1 calc R . . H31B H 1.1726 -0.1128 0.5578 0.059 Uiso 1 1 calc R . . C32 C 1.2930(7) -0.0492(6) 0.6464(6) 0.0358(17) Uani 1 1 d . . . H32A H 1.3919 -0.0559 0.6108 0.043 Uiso 1 1 calc R . . H32B H 1.2440 0.0334 0.6329 0.043 Uiso 1 1 calc R . . N1 N 0.5996(5) 0.2087(4) 0.7568(4) 0.0207(11) Uani 1 1 d . . . N2 N 0.6112(5) 0.3748(4) 0.6500(4) 0.0210(11) Uani 1 1 d . . . Ir1 Ir 0.86176(2) 0.31239(2) 0.755526(18) 0.01980(9) Uani 1 1 d . . . Cl1 Cl 0.94993(16) 0.17482(13) 0.62795(12) 0.0279(3) Uani 1 1 d . . . O1 O 0.4586(5) 0.2700(4) 0.9326(4) 0.0325(11) Uani 1 1 d . . . O2 O 1.2907(5) -0.0716(5) 0.7489(4) 0.0414(12) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.017(3) 0.016(3) 0.022(3) -0.004(2) -0.008(2) -0.003(2) C2 0.021(3) 0.035(4) 0.042(5) 0.006(3) -0.016(3) -0.010(3) C3 0.043(4) 0.030(3) 0.040(5) 0.001(3) -0.022(3) -0.011(3) C4 0.029(3) 0.024(3) 0.037(4) 0.002(3) -0.017(3) -0.006(3) C5 0.023(3) 0.024(3) 0.020(3) -0.001(2) -0.007(3) -0.005(3) C6 0.020(3) 0.027(3) 0.036(4) 0.004(3) -0.007(3) -0.007(3) C7 0.030(3) 0.039(4) 0.024(4) 0.000(3) -0.006(3) -0.012(3) C8 0.035(4) 0.040(4) 0.032(4) 0.010(3) -0.014(3) -0.012(3) C9 0.033(4) 0.030(3) 0.038(5) 0.003(3) -0.011(3) 0.000(3) C10 0.024(3) 0.031(3) 0.029(4) 0.004(3) -0.009(3) -0.006(3) C11 0.042(4) 0.052(5) 0.045(5) -0.021(4) 0.002(4) -0.005(4) C12 0.018(3) 0.022(3) 0.030(4) 0.006(3) -0.011(3) -0.002(2) C13 0.017(3) 0.023(3) 0.027(4) 0.004(3) -0.009(3) -0.005(2) C14 0.026(3) 0.027(3) 0.022(4) -0.003(3) -0.008(3) 0.003(3) C15 0.029(3) 0.025(3) 0.032(4) 0.001(3) -0.014(3) -0.003(3) C16 0.025(3) 0.029(3) 0.021(4) 0.008(3) -0.011(3) -0.006(3) C17 0.025(3) 0.024(3) 0.024(4) 0.001(3) -0.013(3) 0.000(3) C18 0.022(3) 0.033(4) 0.045(5) -0.003(3) -0.002(3) -0.002(3) C19 0.043(4) 0.029(4) 0.050(5) 0.002(3) -0.011(4) -0.009(3) C20 0.039(4) 0.019(3) 0.034(4) -0.004(3) -0.006(3) -0.003(3) C21 0.021(3) 0.032(3) 0.026(4) -0.003(3) -0.012(3) -0.005(3) C22 0.025(3) 0.041(4) 0.026(4) -0.011(3) -0.010(3) -0.009(3) C23 0.047(4) 0.044(4) 0.015(4) 0.000(3) -0.014(3) -0.011(3) C24 0.040(4) 0.032(4) 0.040(5) 0.001(3) -0.020(3) 0.002(3) C25 0.037(4) 0.035(4) 0.034(4) 0.001(3) -0.021(3) -0.004(3) C26 0.014(3) 0.052(4) 0.033(4) -0.004(3) -0.012(3) -0.007(3) C27 0.026(3) 0.046(4) 0.035(4) 0.003(3) -0.010(3) -0.023(3) C28 0.026(3) 0.026(3) 0.034(4) -0.001(3) -0.005(3) -0.005(3) C29 0.055(5) 0.054(5) 0.041(5) 0.004(4) 0.003(4) -0.015(4) C30 0.048(5) 0.059(5) 0.074(7) 0.004(5) -0.010(5) -0.030(4) C31 0.053(5) 0.049(5) 0.052(6) -0.009(4) -0.011(4) -0.021(4) C32 0.036(4) 0.033(4) 0.040(5) 0.001(3) -0.009(3) -0.007(3) N1 0.020(2) 0.022(2) 0.022(3) 0.003(2) -0.009(2) -0.004(2) N2 0.018(2) 0.022(2) 0.026(3) 0.002(2) -0.011(2) -0.007(2) Ir1 0.01635(13) 0.02201(13) 0.02180(15) -0.00083(9) -0.00626(9) -0.00175(9) Cl1 0.0270(8) 0.0260(7) 0.0281(9) -0.0021(6) -0.0029(7) 0.0023(6) O1 0.030(2) 0.033(2) 0.032(3) -0.006(2) 0.002(2) -0.003(2) O2 0.032(3) 0.059(3) 0.034(3) -0.005(2) -0.007(2) -0.009(2) _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 N2 1.335(7) . ? C1 N1 1.342(7) . ? C1 Ir1 2.074(5) . ? C2 N1 1.480(7) . ? C2 C3 1.513(10) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.503(8) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 N2 1.464(7) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C10 1.363(9) . ? C5 C6 1.418(9) . ? C5 N1 1.454(7) . ? C6 O1 1.367(7) . ? C6 C7 1.384(9) . ? C7 C8 1.386(10) . ? C7 H7 0.9500 . ? C8 C9 1.372(11) . ? C8 H8 0.9500 . ? C9 C10 1.403(9) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 O1 1.435(9) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.387(9) . ? C12 C17 1.405(9) . ? C12 N2 1.463(7) . ? C13 C14 1.397(8) . ? C13 C18 1.516(9) . ? C14 C15 1.396(9) . ? C14 H14 0.9500 . ? C15 C16 1.387(10) . ? C15 C19 1.513(8) . ? C16 C17 1.397(8) . ? C16 H16 0.9500 . ? C17 C20 1.499(9) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 C22 1.422(9) . ? C21 C28 1.512(8) . ? C21 Ir1 2.091(6) . ? C21 H21 0.9500 . ? C22 C23 1.523(9) . ? C22 Ir1 2.112(7) . ? C22 H22 0.9500 . ? C23 C24 1.539(10) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.501(11) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 C26 1.402(9) . ? C25 Ir1 2.160(6) . ? C25 H25 0.9500 . ? C26 C27 1.518(10) . ? C26 Ir1 2.187(6) . ? C26 H26 0.9500 . ? C27 C28 1.514(9) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? C29 O2 1.414(9) . ? C29 C30 1.509(12) . ? C29 H29A 0.9900 . ? C29 H29B 0.9900 . ? C30 C31 1.520(12) . ? C30 H30A 0.9900 . ? C30 H30B 0.9900 . ? C31 C32 1.499(10) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 O2 1.424(9) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? Ir1 Cl1 2.3842(17) . ? 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 117.3(5) . . ? N2 C1 Ir1 124.0(4) . . ? N1 C1 Ir1 117.7(4) . . ? N1 C2 C3 107.7(5) . . ? N1 C2 H2A 110.2 . . ? C3 C2 H2A 110.2 . . ? N1 C2 H2B 110.2 . . ? C3 C2 H2B 110.2 . . ? H2A C2 H2B 108.5 . . ? C4 C3 C2 108.9(6) . . ? C4 C3 H3A 109.9 . . ? C2 C3 H3A 109.9 . . ? C4 C3 H3B 109.9 . . ? C2 C3 H3B 109.9 . . ? H3A C3 H3B 108.3 . . ? N2 C4 C3 110.7(5) . . ? N2 C4 H4A 109.5 . . ? C3 C4 H4A 109.5 . . ? N2 C4 H4B 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 108.1 . . ? C10 C5 C6 121.3(6) . . ? C10 C5 N1 122.0(6) . . ? C6 C5 N1 116.6(5) . . ? O1 C6 C7 126.1(6) . . ? O1 C6 C5 115.3(6) . . ? C7 C6 C5 118.6(6) . . ? C6 C7 C8 120.0(7) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C9 C8 C7 120.6(6) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C8 C9 C10 120.5(7) . . ? C8 C9 H9 119.7 . . ? C10 C9 H9 119.7 . . ? C5 C10 C9 118.8(7) . . ? C5 C10 H10 120.6 . . ? C9 C10 H10 120.6 . . ? O1 C11 H11A 109.5 . . ? O1 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O1 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 C17 121.6(5) . . ? C13 C12 N2 117.4(5) . . ? C17 C12 N2 120.8(6) . . ? C12 C13 C14 118.6(6) . . ? C12 C13 C18 121.7(5) . . ? C14 C13 C18 119.6(6) . . ? C15 C14 C13 121.9(6) . . ? C15 C14 H14 119.1 . . ? C13 C14 H14 119.1 . . ? C16 C15 C14 117.4(5) . . ? C16 C15 C19 121.8(6) . . ? C14 C15 C19 120.8(6) . . ? C15 C16 C17 123.2(6) . . ? C15 C16 H16 118.4 . . ? C17 C16 H16 118.4 . . ? C16 C17 C12 117.1(6) . . ? C16 C17 C20 120.9(6) . . ? C12 C17 C20 122.0(5) . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C15 C19 H19A 109.5 . . ? C15 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C15 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C22 C21 C28 125.6(6) . . ? C22 C21 Ir1 71.0(4) . . ? C28 C21 Ir1 113.1(4) . . ? C22 C21 H21 117.2 . . ? C28 C21 H21 117.2 . . ? Ir1 C21 H21 85.8 . . ? C21 C22 C23 122.2(5) . . ? C21 C22 Ir1 69.4(4) . . ? C23 C22 Ir1 114.4(5) . . ? C21 C22 H22 118.9 . . ? C23 C22 H22 118.9 . . ? Ir1 C22 H22 86.4 . . ? C22 C23 C24 111.7(6) . . ? C22 C23 H23A 109.3 . . ? C24 C23 H23A 109.3 . . ? C22 C23 H23B 109.3 . . ? C24 C23 H23B 109.3 . . ? H23A C23 H23B 107.9 . . ? C25 C24 C23 112.9(5) . . ? C25 C24 H24A 109.0 . . ? C23 C24 H24A 109.0 . . ? C25 C24 H24B 109.0 . . ? C23 C24 H24B 109.0 . . ? H24A C24 H24B 107.8 . . ? C26 C25 C24 125.6(7) . . ? C26 C25 Ir1 72.2(3) . . ? C24 C25 Ir1 110.1(5) . . ? C26 C25 H25 117.2 . . ? C24 C25 H25 117.2 . . ? Ir1 C25 H25 87.6 . . ? C25 C26 C27 123.4(7) . . ? C25 C26 Ir1 70.2(3) . . ? C27 C26 Ir1 112.2(4) . . ? C25 C26 H26 118.3 . . ? C27 C26 H26 118.3 . . ? Ir1 C26 H26 87.6 . . ? C28 C27 C26 112.9(5) . . ? C28 C27 H27A 109.0 . . ? C26 C27 H27A 109.0 . . ? C28 C27 H27B 109.0 . . ? C26 C27 H27B 109.0 . . ? H27A C27 H27B 107.8 . . ? C21 C28 C27 112.3(5) . . ? C21 C28 H28A 109.1 . . ? C27 C28 H28A 109.1 . . ? C21 C28 H28B 109.1 . . ? C27 C28 H28B 109.1 . . ? H28A C28 H28B 107.9 . . ? O2 C29 C30 107.9(7) . . ? O2 C29 H29A 110.1 . . ? C30 C29 H29A 110.1 . . ? O2 C29 H29B 110.1 . . ? C30 C29 H29B 110.1 . . ? H29A C29 H29B 108.4 . . ? C29 C30 C31 105.1(6) . . ? C29 C30 H30A 110.7 . . ? C31 C30 H30A 110.7 . . ? C29 C30 H30B 110.7 . . ? C31 C30 H30B 110.7 . . ? H30A C30 H30B 108.8 . . ? C32 C31 C30 102.0(7) . . ? C32 C31 H31A 111.4 . . ? C30 C31 H31A 111.4 . . ? C32 C31 H31B 111.4 . . ? C30 C31 H31B 111.4 . . ? H31A C31 H31B 109.2 . . ? O2 C32 C31 106.7(6) . . ? O2 C32 H32A 110.4 . . ? C31 C32 H32A 110.4 . . ? O2 C32 H32B 110.4 . . ? C31 C32 H32B 110.4 . . ? H32A C32 H32B 108.6 . . ? C1 N1 C5 119.3(5) . . ? C1 N1 C2 123.6(5) . . ? C5 N1 C2 116.6(4) . . ? C1 N2 C12 119.0(5) . . ? C1 N2 C4 125.0(5) . . ? C12 N2 C4 115.0(4) . . ? C1 Ir1 C21 97.8(2) . . ? C1 Ir1 C22 98.6(2) . . ? C21 Ir1 C22 39.6(2) . . ? C1 Ir1 C25 156.1(2) . . ? C21 Ir1 C25 97.0(3) . . ? C22 Ir1 C25 81.4(3) . . ? C1 Ir1 C26 164.8(2) . . ? C21 Ir1 C26 80.7(3) . . ? C22 Ir1 C26 89.8(3) . . ? C25 Ir1 C26 37.6(2) . . ? C1 Ir1 Cl1 84.82(17) . . ? C21 Ir1 Cl1 157.46(18) . . ? C22 Ir1 Cl1 162.36(18) . . ? C25 Ir1 Cl1 88.6(2) . . ? C26 Ir1 Cl1 91.0(2) . . ? C6 O1 C11 116.7(6) . . ? C29 O2 C32 107.7(6) . . ? _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 1.187 _refine_diff_density_min -1.830 _refine_diff_density_rms 0.193