# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_kjc1109 _database_code_depnum_ccdc_archive 'CCDC 905711' #TrackingRef 'kjc1109-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H30 N2, I' _chemical_formula_sum 'C15 H30 I N2' _chemical_formula_weight 365.31 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 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 13.2298(2) _cell_length_b 8.9506(2) _cell_length_c 15.5722(3) _cell_angle_alpha 90.00 _cell_angle_beta 103.0750(10) _cell_angle_gamma 90.00 _cell_volume 1796.17(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2951 _cell_measurement_theta_min 2.64 _cell_measurement_theta_max 28.27 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.351 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 748 _exptl_absorpt_coefficient_mu 1.773 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.5758 _exptl_absorpt_correction_T_max 0.8426 _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 8565 _diffrn_reflns_av_R_equivalents 0.0562 _diffrn_reflns_av_sigmaI/netI 0.0625 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.64 _diffrn_reflns_theta_max 28.27 _reflns_number_total 4426 _reflns_number_gt 2951 _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^)+(0.0622P)^2^+5.3378P] 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 0.0082(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4426 _refine_ls_number_parameters 170 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1126 _refine_ls_R_factor_gt 0.0689 _refine_ls_wR_factor_ref 0.1554 _refine_ls_wR_factor_gt 0.1380 _refine_ls_goodness_of_fit_ref 1.078 _refine_ls_restrained_S_all 1.078 _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 0.4594(4) 0.3481(5) 0.6823(3) 0.0300(11) Uani 1 1 d . . . C2 C 0.3054(4) 0.1805(6) 0.6589(4) 0.0416(13) Uani 1 1 d . . . H2A H 0.2423 0.1789 0.6831 0.050 Uiso 1 1 calc R . . H2B H 0.3356 0.0788 0.6648 0.050 Uiso 1 1 calc R . . C3 C 0.2760(5) 0.2232(7) 0.5626(4) 0.0559(18) Uani 1 1 d . . . H3A H 0.2669 0.3330 0.5583 0.067 Uiso 1 1 calc R . . H3B H 0.2083 0.1769 0.5357 0.067 Uiso 1 1 calc R . . C4 C 0.3542(5) 0.1773(8) 0.5095(4) 0.0584(17) Uani 1 1 d . . . H4A H 0.3341 0.0784 0.4825 0.070 Uiso 1 1 calc R . . H4B H 0.3513 0.2500 0.4611 0.070 Uiso 1 1 calc R . . C5 C 0.4641(5) 0.1687(6) 0.5631(4) 0.0465(14) Uani 1 1 d . . . H5A H 0.4703 0.0828 0.6040 0.056 Uiso 1 1 calc R . . H5B H 0.5112 0.1505 0.5230 0.056 Uiso 1 1 calc R . . C6 C 0.3615(4) 0.3466(6) 0.7927(4) 0.0375(12) Uani 1 1 d . . . H6A H 0.2855 0.3542 0.7866 0.045 Uiso 1 1 calc R . . H6B H 0.3904 0.4489 0.8016 0.045 Uiso 1 1 calc R . . C7 C 0.4073(4) 0.2535(6) 0.8754(4) 0.0405(13) Uani 1 1 d . . . C8 C 0.3814(6) 0.3393(9) 0.9527(5) 0.0647(19) Uani 1 1 d . . . H8A H 0.4115 0.2872 1.0079 0.097 Uiso 1 1 calc R . . H8B H 0.3059 0.3452 0.9449 0.097 Uiso 1 1 calc R . . H8C H 0.4103 0.4404 0.9547 0.097 Uiso 1 1 calc R . . C9 C 0.3592(5) 0.0968(7) 0.8700(4) 0.0499(15) Uani 1 1 d . . . H9A H 0.3858 0.0435 0.9255 0.075 Uiso 1 1 calc R . . H9B H 0.3774 0.0414 0.8213 0.075 Uiso 1 1 calc R . . H9C H 0.2835 0.1053 0.8596 0.075 Uiso 1 1 calc R . . C10 C 0.5252(5) 0.2399(8) 0.8875(4) 0.0547(17) Uani 1 1 d . . . H10A H 0.5554 0.3396 0.8859 0.082 Uiso 1 1 calc R . . H10B H 0.5408 0.1788 0.8398 0.082 Uiso 1 1 calc R . . H10C H 0.5549 0.1926 0.9443 0.082 Uiso 1 1 calc R . . C11 C 0.5820(4) 0.3953(6) 0.5934(4) 0.0394(13) Uani 1 1 d . . . H11A H 0.5725 0.5006 0.6094 0.047 Uiso 1 1 calc R . . H11B H 0.5760 0.3917 0.5289 0.047 Uiso 1 1 calc R . . C12 C 0.6929(4) 0.3457(6) 0.6400(4) 0.0425(13) Uani 1 1 d . . . C13 C 0.7163(5) 0.1870(7) 0.6141(5) 0.0559(17) Uani 1 1 d . . . H13A H 0.7907 0.1671 0.6343 0.084 Uiso 1 1 calc R . . H13B H 0.6961 0.1766 0.5498 0.084 Uiso 1 1 calc R . . H13C H 0.6770 0.1155 0.6414 0.084 Uiso 1 1 calc R . . C14 C 0.7680(5) 0.4521(7) 0.6091(5) 0.0613(18) Uani 1 1 d . . . H14A H 0.7545 0.5547 0.6253 0.092 Uiso 1 1 calc R . . H14B H 0.7580 0.4450 0.5449 0.092 Uiso 1 1 calc R . . H14C H 0.8395 0.4247 0.6372 0.092 Uiso 1 1 calc R . . C15 C 0.7090(5) 0.3537(10) 0.7392(4) 0.0621(19) Uani 1 1 d . . . H15A H 0.6890 0.4529 0.7561 0.093 Uiso 1 1 calc R . . H15B H 0.7823 0.3355 0.7666 0.093 Uiso 1 1 calc R . . H15C H 0.6661 0.2777 0.7592 0.093 Uiso 1 1 calc R . . N1 N 0.3812(3) 0.2870(5) 0.7101(3) 0.0324(9) Uani 1 1 d . . . N2 N 0.4972(3) 0.3057(5) 0.6144(3) 0.0353(10) Uani 1 1 d . . . I1 I 0.45360(3) 0.76410(4) 0.68736(3) 0.0456(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 C1 0.032(2) 0.023(2) 0.035(3) 0.003(2) 0.008(2) 0.005(2) C2 0.038(3) 0.032(3) 0.053(3) -0.002(3) 0.006(3) -0.009(2) C3 0.055(4) 0.046(4) 0.056(4) 0.007(3) -0.010(3) -0.006(3) C4 0.076(5) 0.050(4) 0.044(4) -0.012(3) 0.001(3) -0.011(3) C5 0.061(4) 0.027(3) 0.057(4) -0.012(3) 0.024(3) -0.008(3) C6 0.038(3) 0.031(3) 0.048(3) -0.004(2) 0.017(2) -0.002(2) C7 0.040(3) 0.049(3) 0.037(3) -0.002(3) 0.017(2) 0.000(2) C8 0.079(5) 0.065(5) 0.061(4) -0.011(4) 0.037(4) -0.007(4) C9 0.058(4) 0.045(3) 0.050(4) 0.016(3) 0.019(3) 0.003(3) C10 0.036(3) 0.087(5) 0.042(3) 0.007(3) 0.011(3) -0.003(3) C11 0.057(3) 0.025(3) 0.041(3) 0.004(2) 0.022(3) 0.003(2) C12 0.050(3) 0.026(3) 0.059(4) 0.005(3) 0.026(3) 0.002(2) C13 0.066(4) 0.037(3) 0.073(4) 0.015(3) 0.031(4) 0.012(3) C14 0.063(4) 0.039(3) 0.092(5) 0.011(3) 0.036(4) 0.003(3) C15 0.044(3) 0.098(6) 0.047(4) -0.007(4) 0.017(3) 0.002(4) N1 0.028(2) 0.026(2) 0.044(3) 0.0009(18) 0.0109(19) 0.0000(16) N2 0.045(3) 0.024(2) 0.040(3) -0.0015(19) 0.016(2) -0.0013(19) I1 0.0456(3) 0.0331(3) 0.0623(3) 0.00294(17) 0.02082(19) 0.00494(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N2 1.324(6) . ? C1 N1 1.326(6) . ? C2 N1 1.480(7) . ? C2 C3 1.511(9) . ? C3 C4 1.520(10) . ? C4 C5 1.505(9) . ? C5 N2 1.475(7) . ? C6 N1 1.469(7) . ? C6 C7 1.538(8) . ? C7 C8 1.530(8) . ? C7 C10 1.533(8) . ? C7 C9 1.535(8) . ? C11 N2 1.474(7) . ? C11 C12 1.547(8) . ? C12 C15 1.513(9) . ? C12 C13 1.527(8) . ? C12 C14 1.530(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 127.4(5) . . ? N1 C2 C3 111.3(5) . . ? C2 C3 C4 114.7(5) . . ? C5 C4 C3 113.8(5) . . ? N2 C5 C4 112.9(5) . . ? N1 C6 C7 114.9(4) . . ? C8 C7 C10 110.3(5) . . ? C8 C7 C9 109.8(5) . . ? C10 C7 C9 109.4(5) . . ? C8 C7 C6 105.7(5) . . ? C10 C7 C6 110.0(5) . . ? C9 C7 C6 111.6(5) . . ? N2 C11 C12 115.3(4) . . ? C15 C12 C13 108.9(5) . . ? C15 C12 C14 109.9(6) . . ? C13 C12 C14 108.1(5) . . ? C15 C12 C11 111.4(5) . . ? C13 C12 C11 111.7(5) . . ? C14 C12 C11 106.7(5) . . ? C1 N1 C6 116.3(4) . . ? C1 N1 C2 125.0(4) . . ? C6 N1 C2 118.2(4) . . ? C1 N2 C11 117.7(4) . . ? C1 N2 C5 123.4(4) . . ? C11 N2 C5 118.7(4) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.170 _refine_diff_density_min -1.032 _refine_diff_density_rms 0.127 data_kjc1110t _database_code_depnum_ccdc_archive 'CCDC 905712' #TrackingRef 'kjc1110t-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H40 Cl Ir N2' _chemical_formula_sum 'C22 H40 Cl Ir N2' _chemical_formula_weight 560.21 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' Ir Ir -1.4442 7.9887 '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 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 18.6021(3) _cell_length_b 12.6261(2) _cell_length_c 19.3427(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4543.06(12) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4511 _cell_measurement_theta_min 2.72 _cell_measurement_theta_max 28.31 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.638 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2240 _exptl_absorpt_coefficient_mu 6.004 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.2660 _exptl_absorpt_correction_T_max 0.3797 _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 18940 _diffrn_reflns_av_R_equivalents 0.0630 _diffrn_reflns_av_sigmaI/netI 0.0524 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.72 _diffrn_reflns_theta_max 28.31 _reflns_number_total 5622 _reflns_number_gt 4511 _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^)+(0.0462P)^2^+27.4758P] 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 5622 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0891 _refine_ls_R_factor_gt 0.0646 _refine_ls_wR_factor_ref 0.1249 _refine_ls_wR_factor_gt 0.1163 _refine_ls_goodness_of_fit_ref 1.208 _refine_ls_restrained_S_all 1.208 _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 -0.1225(3) 0.6608(5) 0.2975(4) 0.0138(14) Uani 1 1 d . . . C2 C -0.2360(4) 0.7609(6) 0.3094(4) 0.0219(16) Uani 1 1 d . . . H2A H -0.2534 0.8077 0.3469 0.026 Uiso 1 1 calc R . . H2B H -0.2768 0.7168 0.2935 0.026 Uiso 1 1 calc R . . C3 C -0.2083(4) 0.8274(6) 0.2500(4) 0.0289(18) Uani 1 1 d . . . H3A H -0.1711 0.8773 0.2666 0.035 Uiso 1 1 calc R . . H3B H -0.2481 0.8688 0.2294 0.035 Uiso 1 1 calc R . . C4 C -0.1766(4) 0.7530(6) 0.1966(4) 0.0262(17) Uani 1 1 d . . . H4A H -0.2153 0.7093 0.1761 0.031 Uiso 1 1 calc R . . H4B H -0.1539 0.7946 0.1592 0.031 Uiso 1 1 calc R . . C5 C -0.1790(4) 0.6748(5) 0.4107(4) 0.0176(14) Uani 1 1 d . . . H5A H -0.1773 0.7449 0.4337 0.021 Uiso 1 1 calc R . . H5B H -0.1343 0.6369 0.4233 0.021 Uiso 1 1 calc R . . C6 C -0.2434(4) 0.6122(6) 0.4414(4) 0.0226(16) Uani 1 1 d . . . C7 C -0.3147(5) 0.6739(7) 0.4427(5) 0.041(2) Uani 1 1 d . . . H7A H -0.3500 0.6350 0.4704 0.061 Uiso 1 1 calc R . . H7B H -0.3327 0.6820 0.3954 0.061 Uiso 1 1 calc R . . H7C H -0.3067 0.7440 0.4631 0.061 Uiso 1 1 calc R . . C8 C -0.2531(5) 0.5080(7) 0.4022(5) 0.045(2) Uani 1 1 d . . . H8A H -0.2078 0.4685 0.4026 0.068 Uiso 1 1 calc R . . H8B H -0.2671 0.5231 0.3544 0.068 Uiso 1 1 calc R . . H8C H -0.2907 0.4658 0.4246 0.068 Uiso 1 1 calc R . . C9 C -0.2222(5) 0.5897(8) 0.5164(5) 0.041(2) Uani 1 1 d . . . H9A H -0.2574 0.5415 0.5372 0.061 Uiso 1 1 calc R . . H9B H -0.2213 0.6563 0.5425 0.061 Uiso 1 1 calc R . . H9C H -0.1745 0.5571 0.5176 0.061 Uiso 1 1 calc R . . C10 C -0.0628(4) 0.6515(6) 0.1854(4) 0.0199(15) Uani 1 1 d . . . H10A H -0.0251 0.6198 0.2151 0.024 Uiso 1 1 calc R . . H10B H -0.0420 0.7160 0.1642 0.024 Uiso 1 1 calc R . . C11 C -0.0805(4) 0.5716(6) 0.1264(4) 0.0233(16) Uani 1 1 d . . . C12 C -0.0068(5) 0.5271(8) 0.1035(4) 0.042(2) Uani 1 1 d . . . H12A H 0.0150 0.4878 0.1419 0.063 Uiso 1 1 calc R . . H12B H 0.0249 0.5857 0.0902 0.063 Uiso 1 1 calc R . . H12C H -0.0134 0.4796 0.0640 0.063 Uiso 1 1 calc R . . C13 C -0.1158(5) 0.6242(7) 0.0631(4) 0.033(2) Uani 1 1 d . . . H13A H -0.1192 0.5726 0.0253 0.049 Uiso 1 1 calc R . . H13B H -0.0866 0.6846 0.0481 0.049 Uiso 1 1 calc R . . H13C H -0.1641 0.6488 0.0755 0.049 Uiso 1 1 calc R . . C14 C -0.1274(5) 0.4822(6) 0.1528(4) 0.0303(19) Uani 1 1 d . . . H14A H -0.1743 0.5105 0.1667 0.045 Uiso 1 1 calc R . . H14B H -0.1042 0.4487 0.1927 0.045 Uiso 1 1 calc R . . H14C H -0.1341 0.4296 0.1161 0.045 Uiso 1 1 calc R . . C15 C 0.0290(4) 0.7266(5) 0.3259(4) 0.0186(15) Uani 1 1 d . . . H15 H 0.0010 0.7391 0.2856 0.022 Uiso 1 1 calc R . . C16 C -0.0065(4) 0.7294(5) 0.3910(4) 0.0184(15) Uani 1 1 d . . . H16 H -0.0563 0.7462 0.3912 0.022 Uiso 1 1 calc R . . C17 C 0.0289(4) 0.7077(7) 0.4602(4) 0.0285(18) Uani 1 1 d . . . H17A H -0.0089 0.6968 0.4954 0.034 Uiso 1 1 calc R . . H17B H 0.0573 0.7705 0.4739 0.034 Uiso 1 1 calc R . . C18 C 0.0781(4) 0.6110(6) 0.4593(4) 0.0269(18) Uani 1 1 d . . . H18A H 0.1270 0.6328 0.4447 0.032 Uiso 1 1 calc R . . H18B H 0.0817 0.5815 0.5066 0.032 Uiso 1 1 calc R . . C19 C 0.0507(4) 0.5265(6) 0.4109(4) 0.0208(16) Uani 1 1 d . . . H19 H 0.0163 0.4779 0.4284 0.025 Uiso 1 1 calc R . . C20 C 0.0722(4) 0.5147(6) 0.3426(4) 0.0234(16) Uani 1 1 d . . . H20 H 0.0520 0.4575 0.3173 0.028 Uiso 1 1 calc R . . C21 C 0.1257(4) 0.5863(6) 0.3050(5) 0.0289(18) Uani 1 1 d . . . H21A H 0.1241 0.5706 0.2549 0.035 Uiso 1 1 calc R . . H21B H 0.1748 0.5709 0.3217 0.035 Uiso 1 1 calc R . . C22 C 0.1089(4) 0.7050(6) 0.3165(4) 0.0239(17) Uani 1 1 d . . . H22A H 0.1350 0.7299 0.3581 0.029 Uiso 1 1 calc R . . H22B H 0.1267 0.7459 0.2764 0.029 Uiso 1 1 calc R . . N1 N -0.1784(3) 0.6925(5) 0.3356(3) 0.0175(12) Uani 1 1 d . . . N2 N -0.1224(3) 0.6835(5) 0.2295(3) 0.0199(13) Uani 1 1 d . . . Cl1 Cl -0.08311(10) 0.41376(13) 0.33235(9) 0.0225(4) Uani 1 1 d . . . Ir1 Ir -0.033220(14) 0.586648(19) 0.341277(13) 0.01467(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 0.012(3) 0.009(3) 0.020(3) -0.001(3) -0.011(3) 0.001(2) C2 0.015(4) 0.022(4) 0.029(4) -0.002(3) -0.007(3) 0.011(3) C3 0.028(5) 0.024(4) 0.036(5) 0.006(4) -0.002(4) 0.010(3) C4 0.026(4) 0.027(4) 0.025(4) 0.002(3) -0.007(3) 0.001(3) C5 0.018(4) 0.016(3) 0.018(3) -0.005(3) -0.003(3) 0.003(3) C6 0.020(4) 0.022(4) 0.026(4) -0.003(3) 0.002(3) 0.002(3) C7 0.026(5) 0.043(5) 0.054(6) 0.005(4) 0.015(4) 0.011(4) C8 0.044(5) 0.038(5) 0.053(6) -0.016(5) 0.024(5) -0.019(4) C9 0.033(5) 0.054(6) 0.036(5) 0.007(4) 0.003(4) -0.004(4) C10 0.021(4) 0.022(4) 0.017(3) 0.006(3) 0.001(3) -0.002(3) C11 0.027(4) 0.024(4) 0.019(4) 0.000(3) 0.003(3) -0.004(3) C12 0.046(6) 0.058(6) 0.021(4) -0.012(4) 0.004(4) 0.016(5) C13 0.043(5) 0.034(5) 0.022(4) 0.004(3) -0.001(4) -0.008(4) C14 0.046(5) 0.023(4) 0.022(4) -0.003(3) -0.005(4) -0.013(4) C15 0.013(3) 0.013(3) 0.029(4) 0.000(3) -0.005(3) -0.005(3) C16 0.012(3) 0.017(4) 0.026(4) -0.013(3) -0.001(3) -0.002(3) C17 0.023(4) 0.037(5) 0.026(4) -0.007(3) -0.005(3) 0.001(3) C18 0.018(4) 0.037(5) 0.026(4) -0.001(3) -0.006(3) -0.001(3) C19 0.007(3) 0.025(4) 0.031(4) 0.008(3) -0.005(3) 0.003(3) C20 0.008(3) 0.022(4) 0.040(5) -0.001(3) 0.002(3) 0.004(3) C21 0.023(4) 0.026(4) 0.038(5) -0.006(4) 0.008(4) -0.001(3) C22 0.017(4) 0.027(4) 0.028(4) 0.000(3) 0.008(3) 0.000(3) N1 0.010(3) 0.022(3) 0.021(3) 0.000(2) -0.003(3) 0.002(2) N2 0.024(3) 0.019(3) 0.016(3) -0.001(2) -0.001(3) -0.003(3) Cl1 0.0264(9) 0.0159(8) 0.0252(9) -0.0018(7) -0.0005(7) -0.0026(7) Ir1 0.01362(15) 0.01377(14) 0.01661(15) -0.00053(10) 0.00026(11) 0.00077(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 C1 N1 1.336(9) . ? C1 N2 1.347(9) . ? C1 Ir1 2.085(6) . ? C2 N1 1.467(9) . ? C2 C3 1.513(11) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.513(11) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 N2 1.481(9) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 N1 1.470(9) . ? C5 C6 1.553(10) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C8 1.529(11) . ? C6 C9 1.530(11) . ? C6 C7 1.538(11) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 N2 1.456(9) . ? C10 C11 1.560(10) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C14 1.516(10) . ? C11 C13 1.540(11) . ? C11 C12 1.546(12) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.423(10) . ? C15 C22 1.522(10) . ? C15 Ir1 2.133(6) . ? C15 H15 0.9500 . ? C16 C17 1.515(10) . ? C16 Ir1 2.103(6) . ? C16 H16 0.9500 . ? C17 C18 1.526(11) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.508(11) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.388(11) . ? C19 Ir1 2.197(7) . ? C19 H19 0.9500 . ? C20 C21 1.529(11) . ? C20 Ir1 2.161(7) . ? C20 H20 0.9500 . ? C21 C22 1.547(10) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? Cl1 Ir1 2.3783(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 N1 C1 N2 118.5(6) . . ? N1 C1 Ir1 122.0(5) . . ? N2 C1 Ir1 119.4(5) . . ? N1 C2 C3 109.9(6) . . ? 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 107.8(6) . . ? C2 C3 H3A 110.1 . . ? C4 C3 H3A 110.1 . . ? C2 C3 H3B 110.1 . . ? C4 C3 H3B 110.1 . . ? H3A C3 H3B 108.5 . . ? N2 C4 C3 109.9(6) . . ? 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 . . ? N1 C5 C6 117.5(6) . . ? N1 C5 H5A 107.9 . . ? C6 C5 H5A 107.9 . . ? N1 C5 H5B 107.9 . . ? C6 C5 H5B 107.9 . . ? H5A C5 H5B 107.2 . . ? C8 C6 C9 110.0(7) . . ? C8 C6 C7 110.0(7) . . ? C9 C6 C7 107.5(7) . . ? C8 C6 C5 109.9(6) . . ? C9 C6 C5 105.0(6) . . ? C7 C6 C5 114.4(6) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N2 C10 C11 116.6(6) . . ? N2 C10 H10A 108.2 . . ? C11 C10 H10A 108.2 . . ? N2 C10 H10B 108.2 . . ? C11 C10 H10B 108.2 . . ? H10A C10 H10B 107.3 . . ? C14 C11 C13 110.1(7) . . ? C14 C11 C12 109.7(7) . . ? C13 C11 C12 107.9(7) . . ? C14 C11 C10 110.9(6) . . ? C13 C11 C10 113.2(6) . . ? C12 C11 C10 104.9(6) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C16 C15 C22 124.2(7) . . ? C16 C15 Ir1 69.2(4) . . ? C22 C15 Ir1 113.4(5) . . ? C16 C15 H15 117.9 . . ? C22 C15 H15 117.9 . . ? Ir1 C15 H15 87.4 . . ? C15 C16 C17 125.1(6) . . ? C15 C16 Ir1 71.5(4) . . ? C17 C16 Ir1 110.6(5) . . ? C15 C16 H16 117.4 . . ? C17 C16 H16 117.4 . . ? Ir1 C16 H16 87.8 . . ? C16 C17 C18 113.3(6) . . ? C16 C17 H17A 108.9 . . ? C18 C17 H17A 108.9 . . ? C16 C17 H17B 108.9 . . ? C18 C17 H17B 108.9 . . ? H17A C17 H17B 107.7 . . ? C19 C18 C17 111.7(6) . . ? C19 C18 H18A 109.3 . . ? C17 C18 H18A 109.3 . . ? C19 C18 H18B 109.3 . . ? C17 C18 H18B 109.3 . . ? H18A C18 H18B 107.9 . . ? C20 C19 C18 124.7(7) . . ? C20 C19 Ir1 70.0(4) . . ? C18 C19 Ir1 112.1(5) . . ? C20 C19 H19 117.6 . . ? C18 C19 H19 117.6 . . ? Ir1 C19 H19 87.8 . . ? C19 C20 C21 125.2(7) . . ? C19 C20 Ir1 72.9(4) . . ? C21 C20 Ir1 109.6(5) . . ? C19 C20 H20 117.4 . . ? C21 C20 H20 117.4 . . ? Ir1 C20 H20 87.4 . . ? C20 C21 C22 111.9(6) . . ? C20 C21 H21A 109.2 . . ? C22 C21 H21A 109.2 . . ? C20 C21 H21B 109.2 . . ? C22 C21 H21B 109.2 . . ? H21A C21 H21B 107.9 . . ? C15 C22 C21 112.8(6) . . ? C15 C22 H22A 109.0 . . ? C21 C22 H22A 109.0 . . ? C15 C22 H22B 109.0 . . ? C21 C22 H22B 109.0 . . ? H22A C22 H22B 107.8 . . ? C1 N1 C2 123.6(6) . . ? C1 N1 C5 120.4(6) . . ? C2 N1 C5 115.2(6) . . ? C1 N2 C10 120.9(6) . . ? C1 N2 C4 123.0(6) . . ? C10 N2 C4 115.6(6) . . ? C1 Ir1 C16 89.4(3) . . ? C1 Ir1 C15 90.2(3) . . ? C16 Ir1 C15 39.2(3) . . ? C1 Ir1 C20 156.4(3) . . ? C16 Ir1 C20 98.1(3) . . ? C15 Ir1 C20 81.8(3) . . ? C1 Ir1 C19 165.8(3) . . ? C16 Ir1 C19 81.2(3) . . ? C15 Ir1 C19 89.2(3) . . ? C20 Ir1 C19 37.1(3) . . ? C1 Ir1 Cl1 94.14(18) . . ? C16 Ir1 Cl1 155.8(2) . . ? C15 Ir1 Cl1 164.1(2) . . ? C20 Ir1 Cl1 88.2(2) . . ? C19 Ir1 Cl1 90.3(2) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 2.658 _refine_diff_density_min -2.313 _refine_diff_density_rms 0.235 data_kjc1111 _database_code_depnum_ccdc_archive 'CCDC 905713' #TrackingRef 'kjc1111-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H42 Cl Ir N2' _chemical_formula_sum 'C23 H42 Cl Ir N2' _chemical_formula_weight 574.24 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' Ir Ir -1.4442 7.9887 '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 11.5140(3) _cell_length_b 15.0802(5) _cell_length_c 14.4033(5) _cell_angle_alpha 90.00 _cell_angle_beta 107.804(2) _cell_angle_gamma 90.00 _cell_volume 2381.12(13) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 4384 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 28.27 _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.602 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 5.730 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.4803 _exptl_absorpt_correction_T_max 0.7249 _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 11361 _diffrn_reflns_av_R_equivalents 0.0526 _diffrn_reflns_av_sigmaI/netI 0.0626 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _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 2.70 _diffrn_reflns_theta_max 28.27 _reflns_number_total 5876 _reflns_number_gt 4384 _reflns_threshold_expression >2\s(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^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0909P)^2^+22.8119P] 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 0.0023(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5876 _refine_ls_number_parameters 251 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0928 _refine_ls_R_factor_gt 0.0628 _refine_ls_wR_factor_ref 0.1759 _refine_ls_wR_factor_gt 0.1515 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _refine_ls_shift/su_max 0.017 _refine_ls_shift/su_mean 0.004 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 0.0151(7) 0.4851(6) 0.2693(6) 0.0281(17) Uani 1 1 d . . . C2 C 0.1391(8) 0.4315(6) 0.4298(7) 0.037(2) Uani 1 1 d . . . H2A H 0.1290 0.3809 0.4706 0.044 Uiso 1 1 calc R . . H2B H 0.1091 0.4852 0.4547 0.044 Uiso 1 1 calc R . . C3 C 0.2747(8) 0.4433(7) 0.4433(7) 0.041(2) Uani 1 1 d . . . H3A H 0.3204 0.4403 0.5137 0.049 Uiso 1 1 calc R . . H3B H 0.3032 0.3941 0.4102 0.049 Uiso 1 1 calc R . . C4 C 0.3012(9) 0.5294(7) 0.4031(8) 0.042(2) Uani 1 1 d . . . H4A H 0.3891 0.5326 0.4092 0.051 Uiso 1 1 calc R . . H4B H 0.2819 0.5788 0.4412 0.051 Uiso 1 1 calc R . . C5 C 0.2257(8) 0.5390(7) 0.2957(7) 0.037(2) Uani 1 1 d . . . H5A H 0.2589 0.5894 0.2677 0.045 Uiso 1 1 calc R . . H5B H 0.2368 0.4848 0.2607 0.045 Uiso 1 1 calc R . . C6 C -0.0092(7) 0.3318(6) 0.3133(7) 0.036(2) Uani 1 1 d . . . H6A H -0.0811 0.3388 0.2548 0.043 Uiso 1 1 calc R . . H6B H -0.0397 0.3223 0.3697 0.043 Uiso 1 1 calc R . . C7 C 0.0611(8) 0.2475(6) 0.2998(7) 0.036(2) Uani 1 1 d . . . C8 C 0.1214(9) 0.2591(7) 0.2202(8) 0.043(2) Uani 1 1 d . . . H8A H 0.0585 0.2645 0.1568 0.064 Uiso 1 1 calc R . . H8B H 0.1729 0.2076 0.2194 0.064 Uiso 1 1 calc R . . H8C H 0.1718 0.3129 0.2330 0.064 Uiso 1 1 calc R . . C9 C 0.1563(10) 0.2173(7) 0.3956(8) 0.054(3) Uani 1 1 d . . . H9A H 0.1864 0.1582 0.3866 0.080 Uiso 1 1 calc R . . H9B H 0.1182 0.2154 0.4478 0.080 Uiso 1 1 calc R . . H9C H 0.2245 0.2593 0.4131 0.080 Uiso 1 1 calc R . . C10 C -0.0351(9) 0.1734(6) 0.2696(8) 0.045(2) Uani 1 1 d . . . H10A H -0.0943 0.1882 0.2066 0.067 Uiso 1 1 calc R . . H10B H -0.0773 0.1676 0.3190 0.067 Uiso 1 1 calc R . . H10C H 0.0051 0.1172 0.2641 0.067 Uiso 1 1 calc R . . C11 C 0.0443(8) 0.6398(6) 0.2348(6) 0.0340(19) Uani 1 1 d . . . H11A H -0.0441 0.6322 0.2014 0.041 Uiso 1 1 calc R . . H11B H 0.0829 0.6552 0.1842 0.041 Uiso 1 1 calc R . . C12 C 0.0603(8) 0.7202(6) 0.3049(7) 0.0348(19) Uani 1 1 d . . . C13 C 0.0239(9) 0.6945(7) 0.3950(8) 0.045(2) Uani 1 1 d . . . H13A H 0.0159 0.7481 0.4310 0.068 Uiso 1 1 calc R . . H13B H 0.0867 0.6559 0.4371 0.068 Uiso 1 1 calc R . . H13C H -0.0543 0.6629 0.3746 0.068 Uiso 1 1 calc R . . C14 C 0.1901(9) 0.7563(7) 0.3336(7) 0.043(2) Uani 1 1 d . . . H14A H 0.2096 0.7750 0.2749 0.065 Uiso 1 1 calc R . . H14B H 0.2472 0.7099 0.3670 0.065 Uiso 1 1 calc R . . H14C H 0.1969 0.8072 0.3772 0.065 Uiso 1 1 calc R . . C15 C -0.0247(9) 0.7918(7) 0.2462(9) 0.051(3) Uani 1 1 d . . . H15A H -0.1095 0.7720 0.2311 0.076 Uiso 1 1 calc R . . H15B H -0.0056 0.8028 0.1854 0.076 Uiso 1 1 calc R . . H15C H -0.0134 0.8466 0.2845 0.076 Uiso 1 1 calc R . . C16 C -0.1108(9) 0.5157(6) 0.0521(7) 0.036(2) Uani 1 1 d . . . H16 H -0.0402 0.5448 0.0925 0.043 Uiso 1 1 calc R . . C17 C -0.1221(9) 0.4228(6) 0.0636(7) 0.038(2) Uani 1 1 d . . . H17 H -0.0572 0.3937 0.1109 0.045 Uiso 1 1 calc R . . C18 C -0.2286(11) 0.3663(9) 0.0068(10) 0.066(4) Uani 1 1 d . . . H18A H -0.2287 0.3637 -0.0619 0.079 Uiso 1 1 calc R . . H18B H -0.2158 0.3052 0.0331 0.079 Uiso 1 1 calc R . . C19 C -0.3505(10) 0.3970(8) 0.0083(8) 0.053(3) Uani 1 1 d . . . H19A H -0.4011 0.3445 0.0107 0.063 Uiso 1 1 calc R . . H19B H -0.3905 0.4288 -0.0534 0.063 Uiso 1 1 calc R . . C20 C -0.3479(7) 0.4571(7) 0.0924(7) 0.038(2) Uani 1 1 d . . . H20 H -0.3582 0.4309 0.1494 0.045 Uiso 1 1 calc R . . C21 C -0.3317(8) 0.5473(7) 0.0922(8) 0.045(2) Uani 1 1 d . . . H21 H -0.3335 0.5784 0.1491 0.054 Uiso 1 1 calc R . . C22 C -0.3116(11) 0.6012(9) 0.0119(10) 0.068(4) Uani 1 1 d . . . H22A H -0.2973 0.6636 0.0339 0.082 Uiso 1 1 calc R . . H22B H -0.3869 0.5998 -0.0445 0.082 Uiso 1 1 calc R . . C23 C -0.2062(12) 0.5708(9) -0.0217(9) 0.063(3) Uani 1 1 d . . . H23A H -0.1658 0.6237 -0.0385 0.076 Uiso 1 1 calc R . . H23B H -0.2389 0.5354 -0.0819 0.076 Uiso 1 1 calc R . . N1 N 0.0614(6) 0.4157(5) 0.3289(5) 0.0336(16) Uani 1 1 d . . . N2 N 0.0934(6) 0.5536(5) 0.2767(6) 0.0362(17) Uani 1 1 d . . . Cl1 Cl -0.2263(2) 0.50356(14) 0.32177(17) 0.0334(5) Uani 1 1 d . . . Ir1 Ir -0.16259(3) 0.48846(2) 0.18006(2) 0.03090(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 C1 0.018(3) 0.043(5) 0.018(4) -0.005(3) -0.002(3) 0.005(3) C2 0.036(4) 0.036(5) 0.034(5) -0.003(4) 0.005(4) 0.001(4) C3 0.030(4) 0.048(6) 0.041(6) 0.000(4) 0.004(4) 0.001(4) C4 0.031(5) 0.050(6) 0.043(6) 0.001(5) 0.007(4) -0.005(4) C5 0.027(4) 0.043(5) 0.044(6) -0.004(4) 0.015(4) -0.001(4) C6 0.024(4) 0.037(5) 0.044(6) 0.000(4) 0.008(4) -0.001(3) C7 0.039(5) 0.030(4) 0.041(5) -0.001(4) 0.018(4) -0.001(4) C8 0.049(5) 0.042(5) 0.044(6) 0.000(4) 0.025(5) 0.001(4) C9 0.061(7) 0.042(6) 0.049(7) -0.002(5) 0.005(5) 0.015(5) C10 0.039(5) 0.039(5) 0.062(7) -0.004(5) 0.022(5) -0.005(4) C11 0.032(4) 0.046(5) 0.029(5) 0.000(4) 0.017(4) 0.002(4) C12 0.026(4) 0.040(5) 0.038(5) 0.003(4) 0.009(4) -0.004(3) C13 0.050(6) 0.043(5) 0.047(6) -0.005(5) 0.022(5) 0.006(4) C14 0.046(5) 0.037(5) 0.043(6) -0.003(4) 0.009(4) -0.005(4) C15 0.040(5) 0.039(5) 0.068(8) 0.007(5) 0.008(5) 0.004(4) C16 0.034(4) 0.052(5) 0.021(4) 0.014(4) 0.008(4) -0.001(4) C17 0.043(5) 0.043(5) 0.029(5) -0.002(4) 0.015(4) 0.006(4) C18 0.058(7) 0.063(7) 0.068(8) -0.038(6) 0.008(6) -0.003(6) C19 0.055(6) 0.064(7) 0.037(6) -0.015(5) 0.011(5) -0.022(5) C20 0.023(4) 0.052(5) 0.035(5) 0.003(4) 0.004(4) -0.002(4) C21 0.027(4) 0.055(6) 0.039(6) 0.012(5) -0.010(4) -0.002(4) C22 0.051(7) 0.072(8) 0.076(9) 0.032(7) 0.011(6) 0.000(6) C23 0.075(8) 0.068(8) 0.046(7) 0.027(6) 0.019(6) 0.021(6) N1 0.030(4) 0.031(4) 0.032(4) 0.001(3) 0.000(3) -0.001(3) N2 0.027(3) 0.036(4) 0.045(5) 0.000(3) 0.010(3) -0.003(3) Cl1 0.0356(11) 0.0378(11) 0.0300(11) -0.0039(8) 0.0147(9) -0.0016(8) Ir1 0.0259(2) 0.0346(2) 0.0308(2) 0.00006(13) 0.00664(14) -0.00051(12) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N2 1.354(11) . ? C1 N1 1.356(11) . ? C1 Ir1 2.057(8) . ? C2 N1 1.474(11) . ? C2 C3 1.524(12) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.491(14) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.532(14) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 N2 1.480(11) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 N1 1.484(11) . ? C6 C7 1.551(12) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.522(13) . ? C7 C10 1.539(12) . ? C7 C9 1.545(14) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 N2 1.471(12) . ? C11 C12 1.551(13) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C14 1.525(12) . ? C12 C13 1.531(13) . ? C12 C15 1.527(13) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.422(13) . ? C16 C23 1.521(13) . ? C16 Ir1 2.143(9) . ? C16 H16 0.9500 . ? C17 C18 1.512(14) . ? C17 Ir1 2.120(9) . ? C17 H17 0.9500 . ? C18 C19 1.485(16) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.507(14) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.372(16) . ? C20 Ir1 2.173(8) . ? C20 H20 0.9500 . ? C21 C22 1.489(15) . ? C21 Ir1 2.162(9) . ? C21 H21 0.9500 . ? C22 C23 1.509(17) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? Cl1 Ir1 2.381(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 114.6(7) . . ? N2 C1 Ir1 122.8(6) . . ? N1 C1 Ir1 122.5(6) . . ? N1 C2 C3 115.7(8) . . ? N1 C2 H2A 108.4 . . ? C3 C2 H2A 108.3 . . ? N1 C2 H2B 108.4 . . ? C3 C2 H2B 108.4 . . ? H2A C2 H2B 107.4 . . ? C4 C3 C2 112.1(8) . . ? C4 C3 H3A 109.2 . . ? C2 C3 H3A 109.2 . . ? C4 C3 H3B 109.2 . . ? C2 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? C3 C4 C5 110.7(8) . . ? C3 C4 H4A 109.5 . . ? C5 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? C5 C4 H4B 109.5 . . ? H4A C4 H4B 108.1 . . ? N2 C5 C4 115.8(8) . . ? N2 C5 H5A 108.3 . . ? C4 C5 H5A 108.3 . . ? N2 C5 H5B 108.3 . . ? C4 C5 H5B 108.3 . . ? H5A C5 H5B 107.4 . . ? N1 C6 C7 115.8(7) . . ? N1 C6 H6A 108.3 . . ? C7 C6 H6A 108.3 . . ? N1 C6 H6B 108.3 . . ? C7 C6 H6B 108.3 . . ? H6A C6 H6B 107.4 . . ? C8 C7 C10 109.0(8) . . ? C8 C7 C9 110.2(8) . . ? C10 C7 C9 106.9(8) . . ? C8 C7 C6 112.1(8) . . ? C10 C7 C6 105.8(7) . . ? C9 C7 C6 112.6(8) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? N2 C11 C12 118.0(7) . . ? N2 C11 H11A 107.8 . . ? C12 C11 H11A 107.8 . . ? N2 C11 H11B 107.8 . . ? C12 C11 H11B 107.8 . . ? H11A C11 H11B 107.2 . . ? C14 C12 C13 111.1(8) . . ? C14 C12 C15 107.8(8) . . ? C13 C12 C15 110.7(8) . . ? C14 C12 C11 111.5(8) . . ? C13 C12 C11 110.2(8) . . ? C15 C12 C11 105.3(8) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 C23 123.2(10) . . ? C17 C16 Ir1 69.6(5) . . ? C23 C16 Ir1 112.0(7) . . ? C17 C16 H16 118.4 . . ? C23 C16 H16 118.4 . . ? Ir1 C16 H16 88.4 . . ? C16 C17 C18 125.5(9) . . ? C16 C17 Ir1 71.4(5) . . ? C18 C17 Ir1 110.7(7) . . ? C16 C17 H17 117.3 . . ? C18 C17 H17 117.3 . . ? Ir1 C17 H17 87.9 . . ? C19 C18 C17 115.5(9) . . ? C19 C18 H18A 108.4 . . ? C17 C18 H18A 108.4 . . ? C19 C18 H18B 108.4 . . ? C17 C18 H18B 108.4 . . ? H18A C18 H18B 107.5 . . ? C18 C19 C20 114.4(8) . . ? C18 C19 H19A 108.7 . . ? C20 C19 H19A 108.7 . . ? C18 C19 H19B 108.7 . . ? C20 C19 H19B 108.7 . . ? H19A C19 H19B 107.6 . . ? C21 C20 C19 124.3(9) . . ? C21 C20 Ir1 71.1(5) . . ? C19 C20 Ir1 111.9(6) . . ? C21 C20 H20 117.9 . . ? C19 C20 H20 117.9 . . ? Ir1 C20 H20 87.0 . . ? C20 C21 C22 126.6(11) . . ? C20 C21 Ir1 72.0(5) . . ? C22 C21 Ir1 110.7(7) . . ? C20 C21 H21 116.7 . . ? C22 C21 H21 116.7 . . ? Ir1 C21 H21 87.2 . . ? C21 C22 C23 114.5(10) . . ? C21 C22 H22A 108.6 . . ? C23 C22 H22A 108.6 . . ? C21 C22 H22B 108.7 . . ? C23 C22 H22B 108.6 . . ? H22A C22 H22B 107.6 . . ? C22 C23 C16 115.0(9) . . ? C22 C23 H23A 108.5 . . ? C16 C23 H23A 108.5 . . ? C22 C23 H23B 108.5 . . ? C16 C23 H23B 108.5 . . ? H23A C23 H23B 107.5 . . ? C1 N1 C2 120.2(7) . . ? C1 N1 C6 118.2(7) . . ? C2 N1 C6 115.2(7) . . ? C1 N2 C11 118.6(7) . . ? C1 N2 C5 121.6(8) . . ? C11 N2 C5 116.9(7) . . ? C1 Ir1 C17 93.8(3) . . ? C1 Ir1 C16 93.3(4) . . ? C17 Ir1 C16 39.0(4) . . ? C1 Ir1 C21 157.1(4) . . ? C17 Ir1 C21 96.0(4) . . ? C16 Ir1 C21 81.7(4) . . ? C1 Ir1 C20 165.9(4) . . ? C17 Ir1 C20 81.6(4) . . ? C16 Ir1 C20 91.4(4) . . ? C21 Ir1 C20 36.9(4) . . ? C1 Ir1 Cl1 88.6(3) . . ? C17 Ir1 Cl1 157.4(3) . . ? C16 Ir1 Cl1 163.4(3) . . ? C21 Ir1 Cl1 90.2(3) . . ? C20 Ir1 Cl1 90.8(3) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.993 _refine_diff_density_min -1.504 _refine_diff_density_rms 0.237 data_kjc1112 _database_code_depnum_ccdc_archive 'CCDC 905714' #TrackingRef 'kjc1112.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H28 Br N2' _chemical_formula_sum 'C14 H28 Br N2' _chemical_formula_weight 304.29 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 7.0089(5) _cell_length_b 13.0334(12) _cell_length_c 18.072(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1650.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1659 _cell_measurement_theta_min 2.74 _cell_measurement_theta_max 24.24 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.224 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 644 _exptl_absorpt_coefficient_mu 2.476 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.4778 _exptl_absorpt_correction_T_max 0.8265 _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 2897 _diffrn_reflns_av_R_equivalents 0.0100 _diffrn_reflns_av_sigmaI/netI 0.2224 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_max 25.24 _reflns_number_total 2897 _reflns_number_gt 1659 _reflns_threshold_expression >2\s(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^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0585P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.475(19) _refine_ls_number_reflns 2897 _refine_ls_number_parameters 161 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1654 _refine_ls_R_factor_gt 0.0559 _refine_ls_wR_factor_ref 0.1178 _refine_ls_wR_factor_gt 0.1079 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 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 0.8087(8) 0.1013(5) 0.2978(3) 0.0395(16) Uani 1 1 d . . . C2 C 0.7261(8) -0.0637(4) 0.2415(3) 0.0407(14) Uani 1 1 d . . . H2A H 0.8329 -0.0879 0.2102 0.049 Uiso 1 1 calc R . . H2B H 0.6054 -0.0890 0.2197 0.049 Uiso 1 1 calc R . . C3 C 0.7484(8) -0.1050(4) 0.3188(3) 0.0382(13) Uani 1 1 d . . . H3A H 0.7647 -0.1804 0.3171 0.046 Uiso 1 1 calc R . . H3B H 0.6326 -0.0895 0.3481 0.046 Uiso 1 1 calc R . . C4 C 0.9220(8) -0.0558(4) 0.3551(3) 0.0422(16) Uani 1 1 d . . . H4A H 0.9309 -0.0780 0.4074 0.051 Uiso 1 1 calc R . . H4B H 1.0395 -0.0780 0.3293 0.051 Uiso 1 1 calc R . . C5 C 0.6236(7) 0.1074(4) 0.1855(3) 0.0422(15) Uani 1 1 d . . . H5A H 0.5879 0.1753 0.2057 0.051 Uiso 1 1 calc R . . H5B H 0.5040 0.0706 0.1734 0.051 Uiso 1 1 calc R . . C6 C 0.7373(8) 0.1238(4) 0.1134(3) 0.0449(14) Uani 1 1 d . . . C7 C 0.7635(14) 0.0224(4) 0.0726(3) 0.0591(18) Uani 1 1 d . . . H7A H 0.8013 0.0359 0.0213 0.089 Uiso 1 1 calc R . . H7B H 0.6432 -0.0159 0.0732 0.089 Uiso 1 1 calc R . . H7C H 0.8629 -0.0180 0.0972 0.089 Uiso 1 1 calc R . . C8 C 0.9300(9) 0.1726(5) 0.1310(4) 0.064(2) Uani 1 1 d . . . H8A H 1.0048 0.1258 0.1619 0.096 Uiso 1 1 calc R . . H8B H 0.9098 0.2373 0.1575 0.096 Uiso 1 1 calc R . . H8C H 0.9989 0.1861 0.0848 0.096 Uiso 1 1 calc R . . C9 C 0.6112(12) 0.1975(6) 0.0664(4) 0.082(3) Uani 1 1 d . . . H9A H 0.5924 0.2620 0.0934 0.124 Uiso 1 1 calc R . . H9B H 0.4872 0.1653 0.0570 0.124 Uiso 1 1 calc R . . H9C H 0.6747 0.2117 0.0191 0.124 Uiso 1 1 calc R . . C10 C 0.9965(7) 0.1207(5) 0.4078(3) 0.0391(14) Uani 1 1 d . . . H10A H 0.9742 0.0896 0.4570 0.047 Uiso 1 1 calc R . . H10B H 0.9330 0.1885 0.4075 0.047 Uiso 1 1 calc R . . C11 C 1.2129(8) 0.1374(5) 0.3981(3) 0.0382(15) Uani 1 1 d . . . C12 C 1.3277(9) 0.0423(6) 0.4174(4) 0.068(2) Uani 1 1 d . . . H12A H 1.4638 0.0594 0.4183 0.102 Uiso 1 1 calc R . . H12B H 1.3044 -0.0110 0.3803 0.102 Uiso 1 1 calc R . . H12C H 1.2888 0.0171 0.4663 0.102 Uiso 1 1 calc R . . C13 C 1.2652(10) 0.2223(5) 0.4527(3) 0.0550(17) Uani 1 1 d . . . H13A H 1.4011 0.2387 0.4479 0.083 Uiso 1 1 calc R . . H13B H 1.2390 0.1991 0.5033 0.083 Uiso 1 1 calc R . . H13C H 1.1891 0.2836 0.4421 0.083 Uiso 1 1 calc R . . C14 C 1.2542(8) 0.1717(5) 0.3202(3) 0.0503(15) Uani 1 1 d . . . H14A H 1.1721 0.2300 0.3076 0.075 Uiso 1 1 calc R . . H14B H 1.2291 0.1150 0.2859 0.075 Uiso 1 1 calc R . . H14C H 1.3883 0.1923 0.3162 0.075 Uiso 1 1 calc R . . N1 N 0.7248(6) 0.0496(3) 0.2434(2) 0.0357(11) Uani 1 1 d . . . N2 N 0.9050(6) 0.0556(4) 0.3516(3) 0.0373(12) Uani 1 1 d . . . Br1 Br 1.23007(7) -0.12489(5) 0.18590(4) 0.0497(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 C1 0.035(3) 0.059(4) 0.024(4) 0.003(3) 0.010(3) -0.001(3) C2 0.042(3) 0.035(3) 0.045(4) -0.007(3) -0.005(3) -0.006(3) C3 0.050(3) 0.027(3) 0.038(3) 0.006(3) 0.001(4) -0.001(3) C4 0.057(4) 0.038(4) 0.032(4) -0.004(3) 0.004(3) 0.001(3) C5 0.037(3) 0.049(4) 0.040(4) -0.005(4) -0.009(3) 0.001(3) C6 0.061(4) 0.048(3) 0.026(3) -0.004(3) -0.011(3) 0.008(5) C7 0.076(5) 0.069(4) 0.032(4) -0.006(3) -0.002(4) 0.011(5) C8 0.081(5) 0.074(5) 0.037(5) 0.010(4) 0.007(4) -0.025(4) C9 0.119(7) 0.076(6) 0.052(6) 0.019(5) 0.004(5) 0.037(5) C10 0.055(3) 0.038(4) 0.024(3) -0.004(3) -0.006(3) -0.004(3) C11 0.043(3) 0.040(4) 0.031(3) -0.001(3) 0.005(3) 0.004(3) C12 0.058(5) 0.077(5) 0.069(5) 0.001(4) -0.014(4) 0.015(4) C13 0.053(4) 0.060(4) 0.052(4) -0.014(3) 0.001(4) -0.009(4) C14 0.038(3) 0.070(4) 0.043(4) -0.003(3) 0.008(4) -0.012(3) N1 0.038(3) 0.043(3) 0.026(3) 0.003(2) 0.003(3) -0.002(2) N2 0.046(3) 0.036(3) 0.030(3) -0.003(3) 0.002(3) -0.003(2) Br1 0.0448(3) 0.0441(4) 0.0603(4) -0.0014(3) 0.0010(4) -0.0041(4) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N2 1.326(7) . ? C1 N1 1.329(7) . ? C2 N1 1.476(6) . ? C2 C3 1.505(7) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.524(8) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 N2 1.458(7) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 N1 1.472(7) . ? C5 C6 1.543(8) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.524(8) . ? C6 C8 1.526(8) . ? C6 C9 1.557(8) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 N2 1.471(7) . ? C10 C11 1.542(7) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C14 1.506(7) . ? C11 C12 1.519(8) . ? C11 C13 1.527(7) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? 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 122.6(5) . . ? N1 C2 C3 109.6(4) . . ? 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 109.4(4) . . ? C2 C3 H3A 109.8 . . ? C4 C3 H3A 109.8 . . ? C2 C3 H3B 109.8 . . ? C4 C3 H3B 109.8 . . ? H3A C3 H3B 108.2 . . ? N2 C4 C3 109.5(5) . . ? N2 C4 H4A 109.8 . . ? C3 C4 H4A 109.8 . . ? N2 C4 H4B 109.8 . . ? C3 C4 H4B 109.8 . . ? H4A C4 H4B 108.2 . . ? N1 C5 C6 115.0(4) . . ? N1 C5 H5A 108.5 . . ? C6 C5 H5A 108.5 . . ? N1 C5 H5B 108.5 . . ? C6 C5 H5B 108.5 . . ? H5A C5 H5B 107.5 . . ? C7 C6 C8 110.8(6) . . ? C7 C6 C5 110.5(5) . . ? C8 C6 C5 109.8(4) . . ? C7 C6 C9 109.9(5) . . ? C8 C6 C9 111.0(6) . . ? C5 C6 C9 104.7(5) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? N2 C10 C11 115.6(5) . . ? N2 C10 H10A 108.4 . . ? C11 C10 H10A 108.4 . . ? N2 C10 H10B 108.4 . . ? C11 C10 H10B 108.4 . . ? H10A C10 H10B 107.4 . . ? C14 C11 C12 110.8(5) . . ? C14 C11 C13 110.1(5) . . ? C12 C11 C13 108.4(5) . . ? C14 C11 C10 109.7(4) . . ? C12 C11 C10 112.3(5) . . ? C13 C11 C10 105.4(5) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C1 N1 C5 118.6(4) . . ? C1 N1 C2 121.5(5) . . ? C5 N1 C2 119.8(4) . . ? C1 N2 C4 121.4(5) . . ? C1 N2 C10 118.0(5) . . ? C4 N2 C10 120.6(5) . . ? _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 25.24 _diffrn_measured_fraction_theta_full 0.966 _refine_diff_density_max 0.869 _refine_diff_density_min -0.432 _refine_diff_density_rms 0.080 data_kjc1115t _database_code_depnum_ccdc_archive 'CCDC 905715' #TrackingRef 'kjc1115t.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H25 Cl2 I N2' _chemical_formula_sum 'C12 H25 Cl2 I N2' _chemical_formula_weight 395.14 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pna21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 25.0834(6) _cell_length_b 10.1732(3) _cell_length_c 13.7406(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3506.31(15) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 5458 _cell_measurement_theta_min 1.62 _cell_measurement_theta_max 28.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.497 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1584 _exptl_absorpt_coefficient_mu 2.117 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.6196 _exptl_absorpt_correction_T_max 0.7704 _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 19185 _diffrn_reflns_av_R_equivalents 0.0377 _diffrn_reflns_av_sigmaI/netI 0.0596 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 30.48 _reflns_number_total 8832 _reflns_number_gt 5458 _reflns_threshold_expression >2\s(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^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1186P)^2^+9.8045P] 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 0.0036(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.52(7) _refine_ls_number_reflns 8832 _refine_ls_number_parameters 317 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1184 _refine_ls_R_factor_gt 0.0731 _refine_ls_wR_factor_ref 0.2361 _refine_ls_wR_factor_gt 0.1873 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 -0.7898(5) 0.2435(9) -0.296(2) 0.031(4) Uani 1 1 d . . . H1 H -0.7824 0.2423 -0.2281 0.037 Uiso 1 1 calc R . . C2 C -0.8135(5) 0.3840(16) -0.4333(11) 0.038(3) Uani 1 1 d . . . H2A H -0.8160 0.4799 -0.4448 0.045 Uiso 1 1 calc R . . H2B H -0.8502 0.3479 -0.4344 0.045 Uiso 1 1 calc R . . C3 C -0.7816(6) 0.3223(16) -0.5145(12) 0.052(4) Uani 1 1 d . . . H3A H -0.8017 0.3335 -0.5760 0.063 Uiso 1 1 calc R . . H3B H -0.7477 0.3712 -0.5212 0.063 Uiso 1 1 calc R . . C4 C -0.7688(5) 0.1793(16) -0.5027(11) 0.053(4) Uani 1 1 d . . . H4A H -0.7327 0.1707 -0.4744 0.063 Uiso 1 1 calc R . . H4B H -0.7684 0.1372 -0.5677 0.063 Uiso 1 1 calc R . . C5 C -0.8096(5) 0.1052(16) -0.4362(11) 0.039(4) Uani 1 1 d . . . H5A H -0.8462 0.1358 -0.4511 0.047 Uiso 1 1 calc R . . H5B H -0.8079 0.0098 -0.4498 0.047 Uiso 1 1 calc R . . C6 C -0.7782(5) 0.4757(12) -0.2749(10) 0.051(3) Uani 1 1 d . . . H6 H -0.7657 0.4419 -0.2105 0.062 Uiso 1 1 calc R . . C7 C -0.8257(5) 0.5587(12) -0.2567(12) 0.071(4) Uani 1 1 d . . . H7A H -0.8342 0.6092 -0.3155 0.107 Uiso 1 1 calc R . . H7B H -0.8184 0.6192 -0.2029 0.107 Uiso 1 1 calc R . . H7C H -0.8561 0.5026 -0.2398 0.107 Uiso 1 1 calc R . . C8 C -0.7313(4) 0.5534(11) -0.3208(12) 0.060(4) Uani 1 1 d . . . H8A H -0.7426 0.5908 -0.3831 0.090 Uiso 1 1 calc R . . H8B H -0.7010 0.4940 -0.3314 0.090 Uiso 1 1 calc R . . H8C H -0.7205 0.6244 -0.2767 0.090 Uiso 1 1 calc R . . C9 C -0.7986(4) 0.0132(11) -0.2688(9) 0.037(2) Uani 1 1 d . . . H9 H -0.7968 0.0476 -0.2007 0.044 Uiso 1 1 calc R . . C10 C -0.8503(4) -0.0657(11) -0.2781(10) 0.054(3) Uani 1 1 d . . . H10A H -0.8806 -0.0103 -0.2594 0.081 Uiso 1 1 calc R . . H10B H -0.8487 -0.1426 -0.2351 0.081 Uiso 1 1 calc R . . H10C H -0.8547 -0.0948 -0.3456 0.081 Uiso 1 1 calc R . . C11 C -0.7493(4) -0.0702(11) -0.2854(10) 0.051(3) Uani 1 1 d . . . H11A H -0.7467 -0.0928 -0.3546 0.076 Uiso 1 1 calc R . . H11B H -0.7519 -0.1508 -0.2467 0.076 Uiso 1 1 calc R . . H11C H -0.7176 -0.0207 -0.2657 0.076 Uiso 1 1 calc R . . C12 C -1.0369(5) 0.2507(6) -0.1370(17) 0.024(4) Uani 1 1 d . . . H12 H -1.0245 0.2524 -0.2023 0.029 Uiso 1 1 calc R . . C13 C -1.0596(5) 0.3884(16) 0.0069(10) 0.037(3) Uani 1 1 d . . . H13A H -1.0590 0.4840 0.0201 0.044 Uiso 1 1 calc R . . H13B H -1.0972 0.3590 0.0103 0.044 Uiso 1 1 calc R . . C14 C -1.0289(5) 0.3203(14) 0.0838(11) 0.045(3) Uani 1 1 d . . . H14A H -1.0477 0.3323 0.1465 0.054 Uiso 1 1 calc R . . H14B H -0.9937 0.3634 0.0897 0.054 Uiso 1 1 calc R . . C15 C -1.0200(5) 0.1721(14) 0.0678(12) 0.046(3) Uani 1 1 d . . . H15A H -0.9839 0.1597 0.0401 0.055 Uiso 1 1 calc R . . H15B H -1.0206 0.1280 0.1320 0.055 Uiso 1 1 calc R . . C16 C -1.0588(5) 0.1052(17) 0.0034(10) 0.038(4) Uani 1 1 d . . . H16A H -1.0953 0.1337 0.0212 0.045 Uiso 1 1 calc R . . H16B H -1.0565 0.0092 0.0142 0.045 Uiso 1 1 calc R . . C17 C -1.0229(5) 0.4804(11) -0.1543(10) 0.047(3) Uani 1 1 d . . . H17 H -1.0113 0.4484 -0.2198 0.056 Uiso 1 1 calc R . . C18 C -1.0712(5) 0.5700(12) -0.1670(12) 0.070(4) Uani 1 1 d . . . H18A H -1.1032 0.5163 -0.1771 0.105 Uiso 1 1 calc R . . H18B H -1.0657 0.6271 -0.2236 0.105 Uiso 1 1 calc R . . H18C H -1.0757 0.6241 -0.1086 0.105 Uiso 1 1 calc R . . C19 C -0.9768(4) 0.5522(12) -0.1070(11) 0.056(3) Uani 1 1 d . . . H19A H -0.9869 0.5786 -0.0409 0.084 Uiso 1 1 calc R . . H19B H -0.9680 0.6305 -0.1453 0.084 Uiso 1 1 calc R . . H19C H -0.9458 0.4940 -0.1041 0.084 Uiso 1 1 calc R . . C20 C -1.0485(4) 0.0201(12) -0.1730(10) 0.046(3) Uani 1 1 d . . . H20 H -1.0446 0.0559 -0.2404 0.055 Uiso 1 1 calc R . . C21 C -1.1014(4) -0.0548(12) -0.1680(12) 0.058(3) Uani 1 1 d . . . H21A H -1.1028 -0.1061 -0.1077 0.088 Uiso 1 1 calc R . . H21B H -1.1042 -0.1141 -0.2240 0.088 Uiso 1 1 calc R . . H21C H -1.1311 0.0079 -0.1691 0.088 Uiso 1 1 calc R . . C22 C -1.0000(4) -0.0671(11) -0.1516(10) 0.051(3) Uani 1 1 d . . . H22A H -0.9674 -0.0142 -0.1558 0.077 Uiso 1 1 calc R . . H22B H -0.9984 -0.1385 -0.1994 0.077 Uiso 1 1 calc R . . H22C H -1.0032 -0.1041 -0.0861 0.077 Uiso 1 1 calc R . . N1 N -0.7900(4) 0.3608(14) -0.3363(9) 0.037(3) Uani 1 1 d . . . N2 N -0.7983(4) 0.1281(13) -0.3353(8) 0.032(3) Uani 1 1 d . . . N3 N -1.0391(4) 0.3647(14) -0.0939(9) 0.038(3) Uani 1 1 d . . . N4 N -1.0493(4) 0.1340(14) -0.1036(9) 0.032(2) Uani 1 1 d . . . I1 I -1.20604(4) 0.25541(6) -0.06359(4) 0.0363(3) Uani 1 1 d . . . I2 I -0.95620(3) 0.24558(6) -0.36897(4) 0.0368(3) Uani 1 1 d . . . C23 C -0.8563(5) 0.2126(17) 0.0041(12) 0.064(3) Uani 1 1 d . A 1 H23A H -0.8645 0.1246 0.0310 0.076 Uiso 1 1 calc R A 1 H23B H -0.8173 0.2179 -0.0058 0.076 Uiso 1 1 calc R A 1 Cl1 Cl -0.87507(12) 0.3296(4) 0.0865(5) 0.0852(12) Uani 1 1 d . A 1 Cl2 Cl -0.88866(17) 0.2299(4) -0.1102(6) 0.0577(11) Uani 1 1 d . A 1 C24 C -0.6089(5) 0.2098(16) -0.4300(13) 0.065(3) Uani 1 1 d . B 1 H24A H -0.6196 0.1244 -0.4585 0.078 Uiso 1 1 calc R B 1 H24B H -0.5697 0.2080 -0.4206 0.078 Uiso 1 1 calc R B 1 Cl3 Cl -0.62478(13) 0.3354(4) -0.5121(5) 0.0871(12) Uani 1 1 d . B 1 Cl4 Cl -0.63949(17) 0.2275(4) -0.3174(5) 0.0549(9) Uani 1 1 d . B 1 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 0.027(7) 0.033(9) 0.033(10) -0.001(4) -0.006(7) 0.000(3) C2 0.031(6) 0.043(8) 0.040(8) 0.005(7) -0.001(6) -0.002(5) C3 0.051(7) 0.063(9) 0.042(7) 0.014(6) 0.001(6) -0.010(6) C4 0.055(7) 0.077(10) 0.027(6) -0.003(6) 0.004(5) 0.001(7) C5 0.037(7) 0.043(9) 0.038(8) 0.002(7) -0.005(6) -0.004(6) C6 0.080(8) 0.028(6) 0.045(6) 0.002(5) -0.027(6) 0.000(5) C7 0.107(10) 0.033(6) 0.074(9) -0.003(6) 0.024(9) 0.014(7) C8 0.055(7) 0.035(6) 0.090(10) 0.002(6) -0.028(6) -0.001(5) C9 0.057(6) 0.030(5) 0.024(4) -0.004(4) -0.007(4) -0.002(4) C10 0.065(7) 0.042(6) 0.054(7) 0.010(5) 0.000(6) 0.000(5) C11 0.060(6) 0.037(6) 0.054(7) -0.004(5) -0.018(6) 0.007(5) C12 0.041(8) 0.013(6) 0.019(7) -0.002(2) -0.003(7) 0.003(3) C13 0.039(6) 0.044(8) 0.027(6) -0.014(6) 0.008(6) -0.002(6) C14 0.049(6) 0.055(8) 0.032(6) -0.009(6) -0.003(5) -0.009(5) C15 0.044(6) 0.047(7) 0.045(7) 0.002(6) -0.010(5) 0.005(5) C16 0.040(6) 0.047(9) 0.026(6) 0.013(6) 0.006(5) 0.008(6) C17 0.070(7) 0.028(6) 0.043(6) 0.004(4) 0.009(6) 0.002(6) C18 0.094(9) 0.042(7) 0.074(9) 0.013(6) -0.026(9) 0.000(7) C19 0.055(7) 0.043(6) 0.072(8) -0.007(6) 0.010(6) -0.004(5) C20 0.067(8) 0.034(6) 0.035(6) -0.003(5) 0.002(5) 0.015(5) C21 0.069(7) 0.042(6) 0.065(7) -0.012(6) 0.002(7) -0.005(6) C22 0.057(7) 0.037(6) 0.060(8) -0.001(5) 0.012(6) 0.007(5) N1 0.049(6) 0.032(6) 0.030(6) 0.004(4) -0.004(4) -0.002(4) N2 0.045(5) 0.026(5) 0.025(5) 0.002(4) -0.003(4) 0.003(4) N3 0.044(6) 0.035(6) 0.034(6) -0.005(5) 0.006(4) -0.002(4) N4 0.033(4) 0.033(6) 0.028(5) 0.002(4) 0.007(4) 0.003(3) I1 0.0345(5) 0.0398(7) 0.0346(6) -0.0030(4) -0.0029(6) 0.0015(2) I2 0.0349(6) 0.0412(7) 0.0344(7) 0.0018(4) 0.0045(7) 0.0022(2) C23 0.046(7) 0.095(9) 0.051(8) -0.006(9) -0.002(6) 0.016(7) Cl1 0.0678(19) 0.109(3) 0.079(3) -0.032(2) -0.0086(18) 0.0050(19) Cl2 0.0409(17) 0.073(2) 0.059(3) 0.000(2) 0.0036(17) 0.0051(14) C24 0.059(8) 0.068(8) 0.068(10) -0.003(9) -0.008(7) 0.004(7) Cl3 0.078(2) 0.107(3) 0.077(2) 0.029(2) 0.0123(18) 0.010(2) Cl4 0.0459(18) 0.0685(19) 0.050(2) 0.003(2) -0.0002(16) 0.0030(15) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N2 1.310(18) . ? C1 N1 1.317(19) . ? C1 H1 0.9500 . ? C2 N1 1.476(18) . ? C2 C3 1.51(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.50(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.57(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 N2 1.434(19) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 N1 1.471(17) . ? C6 C7 1.483(16) . ? C6 C8 1.550(17) . ? C6 H6 1.0000 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 N2 1.484(15) . ? C9 C11 1.516(14) . ? C9 C10 1.530(13) . ? C9 H9 1.0000 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 N3 1.304(18) . ? C12 N4 1.311(17) . ? C12 H12 0.9500 . ? C13 C14 1.48(2) . ? C13 N3 1.498(17) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.54(2) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.48(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 N4 1.518(17) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 N3 1.496(17) . ? C17 C19 1.513(15) . ? C17 C18 1.527(15) . ? C17 H17 1.0000 . ? 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 N4 1.500(17) . ? C20 C21 1.531(15) . ? C20 C22 1.534(14) . ? C20 H20 1.0000 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 Cl1 1.709(15) . ? C23 Cl2 1.776(16) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 Cl4 1.737(17) . ? C24 Cl3 1.751(16) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 C1 N1 130(2) . . ? N2 C1 H1 115.2 . . ? N1 C1 H1 115.2 . . ? N1 C2 C3 112.9(10) . . ? N1 C2 H2A 109.0 . . ? C3 C2 H2A 109.0 . . ? N1 C2 H2B 109.0 . . ? C3 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? C4 C3 C2 115.9(10) . . ? C4 C3 H3A 108.3 . . ? C2 C3 H3A 108.3 . . ? C4 C3 H3B 108.3 . . ? C2 C3 H3B 108.3 . . ? H3A C3 H3B 107.4 . . ? C3 C4 C5 113.0(11) . . ? C3 C4 H4A 109.0 . . ? C5 C4 H4A 109.0 . . ? C3 C4 H4B 109.0 . . ? C5 C4 H4B 109.0 . . ? H4A C4 H4B 107.8 . . ? N2 C5 C4 110.9(12) . . ? N2 C5 H5A 109.5 . . ? C4 C5 H5A 109.5 . . ? N2 C5 H5B 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 108.1 . . ? N1 C6 C7 112.7(11) . . ? N1 C6 C8 109.0(11) . . ? C7 C6 C8 112.9(10) . . ? N1 C6 H6 107.3 . . ? C7 C6 H6 107.3 . . ? C8 C6 H6 107.3 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N2 C9 C11 110.1(10) . . ? N2 C9 C10 111.5(9) . . ? C11 C9 C10 112.6(9) . . ? N2 C9 H9 107.5 . . ? C11 C9 H9 107.5 . . ? C10 C9 H9 107.5 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N3 C12 N4 130(2) . . ? N3 C12 H12 115.2 . . ? N4 C12 H12 115.2 . . ? C14 C13 N3 114.0(11) . . ? C14 C13 H13A 108.8 . . ? N3 C13 H13A 108.8 . . ? C14 C13 H13B 108.8 . . ? N3 C13 H13B 108.8 . . ? H13A C13 H13B 107.6 . . ? C13 C14 C15 115.6(10) . . ? C13 C14 H14A 108.4 . . ? C15 C14 H14A 108.4 . . ? C13 C14 H14B 108.4 . . ? C15 C14 H14B 108.4 . . ? H14A C14 H14B 107.4 . . ? C16 C15 C14 116.1(10) . . ? C16 C15 H15A 108.3 . . ? C14 C15 H15A 108.3 . . ? C16 C15 H15B 108.3 . . ? C14 C15 H15B 108.3 . . ? H15A C15 H15B 107.4 . . ? C15 C16 N4 112.8(12) . . ? C15 C16 H16A 109.0 . . ? N4 C16 H16A 109.0 . . ? C15 C16 H16B 109.0 . . ? N4 C16 H16B 109.0 . . ? H16A C16 H16B 107.8 . . ? N3 C17 C19 110.4(10) . . ? N3 C17 C18 108.5(10) . . ? C19 C17 C18 111.5(10) . . ? N3 C17 H17 108.8 . . ? C19 C17 H17 108.8 . . ? C18 C17 H17 108.8 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N4 C20 C21 110.1(10) . . ? N4 C20 C22 109.6(10) . . ? C21 C20 C22 113.0(10) . . ? N4 C20 H20 108.0 . . ? C21 C20 H20 108.0 . . ? C22 C20 H20 108.0 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C20 C22 H22A 109.5 . . ? C20 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C20 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C1 N1 C6 118.5(15) . . ? C1 N1 C2 121.8(17) . . ? C6 N1 C2 118.1(13) . . ? C1 N2 C5 125.3(17) . . ? C1 N2 C9 116.8(14) . . ? C5 N2 C9 117.8(13) . . ? C12 N3 C17 115.9(13) . . ? C12 N3 C13 125.3(16) . . ? C17 N3 C13 118.7(13) . . ? C12 N4 C20 118.3(14) . . ? C12 N4 C16 123.5(15) . . ? C20 N4 C16 118.0(13) . . ? Cl1 C23 Cl2 113.0(8) . . ? Cl1 C23 H23A 109.0 . . ? Cl2 C23 H23A 109.0 . . ? Cl1 C23 H23B 109.0 . . ? Cl2 C23 H23B 109.0 . . ? H23A C23 H23B 107.8 . . ? Cl4 C24 Cl3 113.4(8) . . ? Cl4 C24 H24A 108.9 . . ? Cl3 C24 H24A 108.9 . . ? Cl4 C24 H24B 108.9 . . ? Cl3 C24 H24B 108.9 . . ? H24A C24 H24B 107.7 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.019 _refine_diff_density_min -1.178 _refine_diff_density_rms 0.186