# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 loop_ _publ_author_name _publ_author_address 'Barbara Messerle' ; School of Chemistry, The University of New South Wales Sydney, N. S. W. 2052, Australia ; 'Odile Eisenstein' ; Institut Charles Gerhardt, Universite Montpellier 2, CNRS 5253, cc 1501, Place Eugene Bataillon 34095 Montpellier Cedex 5, France ; 'Danielle F Kennedy' ; Research School of Chemistry, The Australian National University, Canberra, A. C. T. 0200, Australia ; 'Ainara Nova' ; Institut Charles Gerhardt, Universite Montpellier 2, CNRS 5253, cc 1501, Place Eugene Bataillon 34095 Montpellier Cedex 5, France ; 'Anthony C Willis' ; School of Chemistry, The University of New South Wales Sydney, N. S. W. 2052, Australia. ; _publ_contact_author_name 'Barbara Messerle' _publ_contact_author_email B.MESSERLE@UNSW.EDU.AU _publ_section_title ; The mechanism of N-vinylindole formation via tandem imine formation and cycloisomerisation of o-ethynylanilines ; _journal_coden_ASTM ? _journal_coeditor_code ? _journal_coeditor_name ? _journal_coeditor_notes ; ? ; _journal_date_accepted ? _journal_date_from_coeditor ? _journal_date_printers_final ? _journal_date_printers_first ? _journal_date_proofs_in ? _journal_date_proofs_out ? #============================================================================= # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_volume ? _journal_year ? _publ_contact_author_address ; Research School of Chemistry, Australian National University, Canberra, A. C. T. 0200, Australia ; _publ_contact_author_fax ' 61 2 6125 0750 ' _publ_contact_author_phone ' 61 2 6125 4109 ' _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_category 'FM ' _publ_requested_coeditor_name ? # Attachment 'nsw0616.cif' data_nsw0616 _database_code_depnum_ccdc_archive 'CCDC 741292' _audit_creation_date 06-07-03 _audit_creation_method CRYSTALS_ver_12.18 _oxford_structure_analysis_title '7031225 nsw0616' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 8.8981(1) _cell_length_b 11.8148(2) _cell_length_c 24.1539(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2539.28(6) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 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' 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' Ir -1.4442 7.9887 27.3049 1.5928 16.7296 8.8655 15.6115 0.4179 5.8338 45.0011 11.4722 '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' _cell_formula_units_Z 4 # Given Formula = C25 H31 Cl4 Ir1 N1 # Dc = 1.78 Fooo = 1320.00 Mu = 56.93 M = 679.56 # Found Formula = C25 H28 Cl4 Ir1 N1 # Dc = 1.77 FOOO = 1320.00 Mu = 56.92 M = 676.53 _chemical_formula_sum 'C25 H28 Cl4 Ir N' _chemical_formula_moiety 'C24 H26 Cl2 Ir N, C H2 Cl2' _chemical_compound_source ' from UNSW' _chemical_formula_weight 676.53 _cell_measurement_reflns_used 30440 _cell_measurement_theta_min 3 _cell_measurement_theta_max 27.5 _cell_measurement_temperature 200 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_min 0.09 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_max 0.26 _exptl_crystal_density_diffrn 1.770 _exptl_crystal_density_meas 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1320 _exptl_absorpt_coefficient_mu 5.692 # Sheldrick geometric approximatio 0.53 0.60 # Absorption correction loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 0 0 0.120 -1 0 0 0.140 0 1 0 0.020 0 2 3 0.050 0 -2 -3 0.060 0 -2 3 0.085 0 2 -3 0.001 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.367 _exptl_absorpt_correction_T_max 0.661 _exptl_absorpt_process_details ; via Gaussian method (Coppens, 1970) implemented in maXus (2000) ; #_diffrn_reflns_av_R_equivalents 0.022 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method ' \f and \w scans with CCD ' _diffrn_special_details ; CCD data collecting conditions- phi and omega scans of width 1.2 deg at rate 53 sec/frame, crystal-detector distance 40mm, multiple scan sets so over 95 percent of data collected with 4-fold redundancy or more [assuming Friedel's Law]. ; # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius BV, 1997)' _computing_data_reduction 'Denzo/Scalepack (Otwinowski & Minor, 1997)' _computing_cell_refinement 'Denzo/Scalepack ' _computing_structure_solution 'SIR92 (Altomare et al, 1994)' _computing_structure_refinement 'CRYSTALS (Watkin et al 2003)' _computing_publication_material 'CRYSTALS ' _computing_molecular_graphics ; ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997) ; _diffrn_standards_interval_time ? _diffrn_standards_interval_count ? _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 200 _diffrn_reflns_number 29393 _reflns_number_total 5831 _diffrn_reflns_av_R_equivalents 0.028 # Number of reflections with Friedels Law is 29393 # Number of reflections without Friedels Law is 5831 # Theoretical number of reflections is about 2922 _diffrn_reflns_theta_min 2.843 _diffrn_reflns_theta_max 27.516 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.516 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _reflns_limit_h_min -11 _reflns_limit_h_max 11 _reflns_limit_k_min 0 _reflns_limit_k_max 15 _reflns_limit_l_min 0 _reflns_limit_l_max 31 _oxford_diffrn_Wilson_B_factor 1.95 _oxford_diffrn_Wilson_scale 16.93 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -1.00 _refine_diff_density_max 0.79 _refine_ls_number_reflns 5819 _refine_ls_number_restraints 0 _refine_ls_number_parameters 281 #_refine_ls_R_factor_ref 0.0177 _refine_ls_wR_factor_ref 0.0302 _refine_ls_goodness_of_fit_ref 0.9414 #_reflns_number_all 5819 _refine_ls_R_factor_all 0.0177 _refine_ls_wR_factor_all 0.0302 # No actual I/u(I) cutoff was used for refinement. The # threshold below is used for "_gt" information ONLY: _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 5566 _refine_ls_R_factor_gt 0.0163 _refine_ls_wR_factor_gt 0.0291 _refine_ls_shift/su_max 0.002348 _refine_ls_abs_structure_Flack -0.019(4) _refine_ls_abs_structure_details 'Flack (1983), 2523 Friedel-pairs' # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration ad _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment noref # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 11.3 13.6 4.60 ; #============================================================================== # 4. TEXT _publ_section_abstract #Text of the abstract ; The crystal structure of [(C~10~H~15~)IrCl~2~(C~14~H~11~N)].CH~2~Cl~2~ is reported. ; _publ_section_comment #Text of the paper ; The crystallographic asymmetric unit consists of one [(C~10~H~15~)IrCl~2~(C~14~H~11~N)] molecule and one dichloromethane molecule of solvation. This crystal contains only one enantiomer of the molecule. In solution the compound is presumably racemic but upon crystallisation it appears to have spontaneously resolved to give a racemic conglomerate. The absolute configuration of molecules in the crystal used to collect the X-ray diffraction data has been determined by refinement of the Flack parameter. The biggest peaks in the final difference electron density map all have similar intensities and are located near the dichloromethane molecule and near the Ir atom. ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions #Captions to figures ; ? ; _publ_section_exptl_refinement # see also _refine_ls_hydrogen for refinement keywords. ; H atoms were included at idealized positions, and ride on the atom to which they are attached. ; _publ_section_exptl_prep ; The compound was prepared by DFK and recrystallized from dichloromethane/hexane. The sample ID was DFK671B. ; _refine_special_details ; The crystallographic asymmetric unit consists of one [(C~10~H~15~)IrCl~2~(C~14~H~11~N)] molecule and one dichloromethane molecule of solvation. This crystal contains only one enantiomer of the molecule. In solution the compound is presumably racemic but upon crystallisation it appears to have spontaneously resolved to give a racemic conglomerate. The absolute configuration of molecules in the crystal used to collect the X-ray diffraction data has been determined by refinement of the Flack parameter. The biggest peaks in the final difference electron density map all have similar intensities and are located near the dichloromethane molecule and near the Ir atom. ; #**************************************************************************** # Insert your own references if required - in alphabetical order _publ_section_references ; Mackay, S., Gilmore, C. J., Edwards, C., Stewart, N. & Shankland, K. (2000). maXus Computer Program for the Solution and Refinement of Crystal Structures. Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Coppens, P. (1970). The Evaluation of Absorption and Extinction in Single-Crystal Structure Analysis. Crystallographic Computing. F. R. Ahmed, S. R. Hall and C. P. Huber, eds., Munksgaard. Copenhagen. pp 255-270. Flack, H.D. (1983) Acta Cryst., A39, 876-881. Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435 Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius BV, COLLECT Software, 1997-2001) Otwinowski, Z. & Minor, W. (1996), Processing of X-ray Diffraction Data Collected in Oscillation Mode. Methods Enzymol. 276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994), Acta Cryst, A50, 411-437 Molecular Structure Corporation. (1992-1997). teXsan. Single Crystal Structure Analysis Software. Version 1.8. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Johnson, C.K. (1976) ORTEP-II, A Fortran Thermal-Ellipsoid Plot Program, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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 Ir1 Ir 0.566312(15) 0.652232(11) 0.604714(5) 0.0221 1.0000 Uani . . . . . . Cl1 Cl 0.36915(10) 0.76839(8) 0.64343(4) 0.0404 1.0000 Uani . . . . . . Cl2 Cl 0.60522(9) 0.78665(7) 0.53060(3) 0.0338 1.0000 Uani . . . . . . Cl3 Cl 0.69042(14) 0.04922(12) 0.65129(6) 0.0671 1.0000 Uani . . . . . . Cl4 Cl 0.38287(14) 0.11468(10) 0.62624(6) 0.0685 1.0000 Uani . . . . . . N1 N 0.3776(3) 0.6036(2) 0.55238(11) 0.0273 1.0000 Uani . . . . . . C1 C 0.3871(3) 0.5023(3) 0.51997(13) 0.0266 1.0000 Uani . . . . . . C2 C 0.4803(4) 0.4995(3) 0.47399(14) 0.0318 1.0000 Uani . . . . . . C3 C 0.4934(4) 0.3994(3) 0.44378(15) 0.0386 1.0000 Uani . . . . . . C4 C 0.4155(5) 0.3040(3) 0.45922(14) 0.0375 1.0000 Uani . . . . . . C5 C 0.3214(4) 0.3066(3) 0.50505(15) 0.0339 1.0000 Uani . . . . . . C6 C 0.3068(4) 0.4057(3) 0.53635(13) 0.0275 1.0000 Uani . . . . . . C7 C 0.2174(4) 0.4084(3) 0.58547(14) 0.0306 1.0000 Uani . . . . . . C8 C 0.1478(4) 0.4151(3) 0.62752(15) 0.0322 1.0000 Uani . . . . . . C9 C 0.0603(4) 0.4214(2) 0.67777(12) 0.0286 1.0000 Uani . . . . . . C10 C -0.0419(4) 0.3351(3) 0.69131(13) 0.0327 1.0000 Uani . . . . . . C11 C -0.1240(4) 0.3408(4) 0.73944(14) 0.0386 1.0000 Uani . . . . . . C12 C -0.1086(4) 0.4324(3) 0.77480(16) 0.0424 1.0000 Uani . . . . . . C13 C -0.0093(4) 0.5184(3) 0.76126(17) 0.0448 1.0000 Uani . . . . . . C14 C 0.0743(5) 0.5140(3) 0.71299(14) 0.0379 1.0000 Uani . . . . . . C15 C 0.6596(3) 0.4885(2) 0.62676(13) 0.0253 1.0000 Uani . . . . . . C16 C 0.6171(3) 0.5490(3) 0.67576(13) 0.0281 1.0000 Uani . . . . . . C17 C 0.7064(3) 0.6530(3) 0.67747(12) 0.0298 1.0000 Uani . . . . . . C18 C 0.7994(3) 0.6550(3) 0.62940(11) 0.0269 1.0000 Uani . . . . . . C19 C 0.7683(3) 0.5552(2) 0.59657(13) 0.0243 1.0000 Uani . . . . . . C20 C 0.6073(3) 0.3733(2) 0.61127(16) 0.0343 1.0000 Uani . . . . . . C21 C 0.5095(4) 0.5103(4) 0.71924(15) 0.0410 1.0000 Uani . . . . . . C22 C 0.7014(5) 0.7395(3) 0.72227(15) 0.0435 1.0000 Uani . . . . . . C23 C 0.9120(4) 0.7441(3) 0.61545(15) 0.0383 1.0000 Uani . . . . . . C24 C 0.8429(4) 0.5236(3) 0.54346(14) 0.0350 1.0000 Uani . . . . . . C25 C 0.5430(6) 0.0372(4) 0.6044(2) 0.0669 1.0000 Uani . . . . . . H11 H 0.3017 0.5965 0.57346 0.0328 1.0000 Uiso R . . . . . H12 H 0.3627 0.6579 0.52995 0.0328 1.0000 Uiso R . . . . . H21 H 0.5375 0.5686 0.46260 0.0382 1.0000 Uiso R . . . . . H31 H 0.5603 0.3969 0.41052 0.0463 1.0000 Uiso R . . . . . H41 H 0.4267 0.2326 0.43739 0.0450 1.0000 Uiso R . . . . . H51 H 0.2639 0.2373 0.51577 0.0407 1.0000 Uiso R . . . . . H101 H -0.0549 0.2691 0.66580 0.0393 1.0000 Uiso R . . . . . H111 H -0.1953 0.2784 0.74900 0.0463 1.0000 Uiso R . . . . . H121 H -0.1687 0.4365 0.80975 0.0509 1.0000 Uiso R . . . . . H131 H 0.0022 0.5846 0.78671 0.0538 1.0000 Uiso R . . . . . H141 H 0.1446 0.5771 0.70346 0.0455 1.0000 Uiso R . . . . . H201 H 0.6752 0.3154 0.62825 0.0412 1.0000 Uiso R . . . . . H202 H 0.5024 0.3617 0.62508 0.0412 1.0000 Uiso R . . . . . H203 H 0.6090 0.3652 0.57006 0.0412 1.0000 Uiso R . . . . . H211 H 0.5641 0.4635 0.74724 0.0493 1.0000 Uiso R . . . . . H212 H 0.4638 0.5777 0.73785 0.0493 1.0000 Uiso R . . . . . H213 H 0.4284 0.4639 0.70174 0.0493 1.0000 Uiso R . . . . . H221 H 0.7777 0.7205 0.75122 0.0522 1.0000 Uiso R . . . . . H222 H 0.7242 0.8158 0.70638 0.0522 1.0000 Uiso R . . . . . H223 H 0.5990 0.7404 0.73930 0.0522 1.0000 Uiso R . . . . . H231 H 1.0112 0.7240 0.63225 0.0459 1.0000 Uiso R . . . . . H232 H 0.8776 0.8186 0.63044 0.0459 1.0000 Uiso R . . . . . H233 H 0.9228 0.7495 0.57433 0.0459 1.0000 Uiso R . . . . . H241 H 0.9352 0.4782 0.55147 0.0420 1.0000 Uiso R . . . . . H242 H 0.8713 0.5938 0.52285 0.0420 1.0000 Uiso R . . . . . H243 H 0.7721 0.4776 0.52046 0.0420 1.0000 Uiso R . . . . . H251 H 0.5151 -0.0444 0.6007 0.0802 1.0000 Uiso R . . . . . H252 H 0.5767 0.0668 0.5676 0.0802 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 Ir1 0.02179(4) 0.02135(4) 0.02314(4) 0.00078(6) -0.00031(5) 0.00082(5) Cl1 0.0367(4) 0.0435(5) 0.0410(5) -0.0091(4) 0.0051(4) 0.0125(4) Cl2 0.0350(5) 0.0324(4) 0.0340(4) 0.0113(3) -0.0008(3) -0.0017(3) Cl3 0.0537(7) 0.0743(8) 0.0732(8) 0.0129(7) 0.0146(6) 0.0058(6) Cl4 0.0626(7) 0.0534(7) 0.0895(9) 0.0102(6) -0.0162(6) -0.0026(5) N1 0.0238(13) 0.0253(13) 0.0329(14) 0.0001(11) -0.0079(11) -0.0019(10) C1 0.0267(16) 0.0271(15) 0.0260(15) -0.0027(13) -0.0090(12) 0.0009(12) C2 0.0300(18) 0.0349(18) 0.0305(17) 0.0058(14) -0.0020(13) -0.0042(13) C3 0.0387(19) 0.049(2) 0.0284(18) -0.0041(16) 0.0009(15) -0.0001(16) C4 0.042(2) 0.0352(17) 0.0356(17) -0.0119(14) -0.0021(17) -0.0016(17) C5 0.0342(18) 0.0312(17) 0.0363(18) -0.0032(14) -0.0050(15) -0.0049(14) C6 0.0217(15) 0.0300(16) 0.0308(16) 0.0005(13) -0.0039(13) -0.0001(13) C7 0.0261(16) 0.0303(17) 0.0356(18) 0.0011(13) -0.0038(14) -0.0046(14) C8 0.0260(17) 0.0332(18) 0.0375(18) 0.0051(14) -0.0035(14) -0.0021(14) C9 0.0214(14) 0.0325(15) 0.0319(15) 0.0079(12) -0.0029(15) 0.0034(15) C10 0.0338(19) 0.0301(17) 0.0343(15) 0.0036(15) -0.0003(14) -0.0060(15) C11 0.0326(16) 0.0416(19) 0.0415(18) 0.0103(19) 0.0030(14) 0.0014(18) C12 0.037(2) 0.050(2) 0.040(2) 0.0031(17) 0.0077(15) 0.0080(16) C13 0.044(2) 0.045(2) 0.046(2) -0.0100(18) 0.0016(17) 0.0057(17) C14 0.0358(18) 0.0346(17) 0.0433(18) -0.0012(14) 0.0017(19) -0.0001(18) C15 0.0245(15) 0.0180(14) 0.0334(16) 0.0077(12) -0.0058(12) 0.0059(11) C16 0.0280(15) 0.0329(16) 0.0234(15) 0.0109(13) -0.0044(12) 0.0051(13) C17 0.0291(15) 0.0357(16) 0.0245(14) 0.0019(16) -0.0091(12) 0.0012(17) C18 0.0213(13) 0.0297(14) 0.0297(14) 0.0034(15) -0.0045(11) 0.0008(15) C19 0.0161(12) 0.0278(14) 0.0289(17) 0.0022(13) -0.0010(12) 0.0065(11) C20 0.0286(15) 0.0246(15) 0.050(2) 0.0059(15) -0.0090(15) 0.0003(11) C21 0.037(2) 0.050(2) 0.035(2) 0.0099(17) 0.0059(16) -0.0013(17) C22 0.052(2) 0.049(2) 0.0300(18) -0.0057(17) -0.0077(17) 0.0009(19) C23 0.0314(18) 0.0365(16) 0.047(2) 0.0036(15) -0.0032(16) -0.0112(15) C24 0.0273(17) 0.039(2) 0.0390(19) -0.0002(15) 0.0035(15) 0.0039(15) C25 0.098(4) 0.049(2) 0.053(2) -0.015(3) 0.013(3) -0.007(3) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.31884(7) 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 Ir1 . Cl1 . 2.4157(8) yes Ir1 . Cl2 . 2.4179(8) yes Ir1 . N1 . 2.179(2) yes Ir1 . C15 . 2.172(3) yes Ir1 . C16 . 2.153(3) yes Ir1 . C17 . 2.155(3) yes Ir1 . C18 . 2.158(3) yes Ir1 . C19 . 2.141(3) yes Cl3 . C25 . 1.739(6) yes Cl4 . C25 . 1.774(5) yes N1 . C1 . 1.433(4) yes N1 . H11 . 0.850 no N1 . H12 . 0.850 no C1 . C2 . 1.387(4) yes C1 . C6 . 1.404(4) yes C2 . C3 . 1.395(5) yes C2 . H21 . 1.000 no C3 . C4 . 1.375(5) yes C3 . H31 . 1.000 no C4 . C5 . 1.388(5) yes C4 . H41 . 1.000 no C5 . C6 . 1.400(4) yes C5 . H51 . 1.000 no C6 . C7 . 1.429(5) yes C7 . C8 . 1.192(4) yes C8 . C9 . 1.444(5) yes C9 . C10 . 1.405(4) yes C9 . C14 . 1.391(4) yes C10 . C11 . 1.375(4) yes C10 . H101 . 1.000 no C11 . C12 . 1.386(5) yes C11 . H111 . 1.000 no C12 . C13 . 1.386(5) yes C12 . H121 . 1.000 no C13 . C14 . 1.384(5) yes C13 . H131 . 1.000 no C14 . H141 . 1.000 no C15 . C16 . 1.434(4) yes C15 . C19 . 1.445(4) yes C15 . C20 . 1.486(4) yes C16 . C17 . 1.464(5) yes C16 . C21 . 1.493(4) yes C17 . C18 . 1.426(4) yes C17 . C22 . 1.489(5) yes C18 . C19 . 1.448(4) yes C18 . C23 . 1.492(4) yes C19 . C24 . 1.492(4) yes C20 . H201 . 1.000 no C20 . H202 . 1.000 no C20 . H203 . 1.000 no C21 . H211 . 1.000 no C21 . H212 . 1.000 no C21 . H213 . 1.000 no C22 . H221 . 1.000 no C22 . H222 . 1.000 no C22 . H223 . 1.000 no C23 . H231 . 1.000 no C23 . H232 . 1.000 no C23 . H233 . 1.000 no C24 . H241 . 1.000 no C24 . H242 . 1.000 no C24 . H243 . 1.000 no C25 . H251 . 1.000 no C25 . H252 . 1.000 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 Cl1 . Ir1 . Cl2 . 91.00(3) yes Cl1 . Ir1 . N1 . 79.31(7) yes Cl2 . Ir1 . N1 . 81.60(7) yes Cl1 . Ir1 . C15 . 133.53(9) yes Cl2 . Ir1 . C15 . 135.40(9) yes N1 . Ir1 . C15 . 101.65(10) yes Cl1 . Ir1 . C16 . 99.53(9) yes Cl2 . Ir1 . C16 . 158.75(9) yes N1 . Ir1 . C16 . 118.34(11) yes C15 . Ir1 . C16 . 38.72(12) yes Cl1 . Ir1 . C17 . 95.86(9) yes Cl2 . Ir1 . C17 . 121.20(10) yes N1 . Ir1 . C17 . 156.96(12) yes C15 . Ir1 . C17 . 65.34(13) yes C16 . Ir1 . C17 . 39.75(13) yes Cl1 . Ir1 . C18 . 125.61(9) yes Cl2 . Ir1 . C18 . 93.26(9) yes N1 . Ir1 . C18 . 154.82(11) yes C15 . Ir1 . C18 . 65.08(13) yes C16 . Ir1 . C18 . 65.60(12) yes Cl1 . Ir1 . C19 . 161.71(9) yes Cl2 . Ir1 . C19 . 99.42(8) yes N1 . Ir1 . C19 . 116.91(11) yes C15 . Ir1 . C19 . 39.15(11) yes C16 . Ir1 . C19 . 66.03(12) yes C17 . Ir1 . C18 . 38.61(11) yes C17 . Ir1 . C19 . 65.89(12) yes C18 . Ir1 . C19 . 39.37(12) yes Ir1 . N1 . C1 . 119.44(19) yes Ir1 . N1 . H11 . 106.9 no C1 . N1 . H11 . 106.9 no Ir1 . N1 . H12 . 106.9 no C1 . N1 . H12 . 106.9 no H11 . N1 . H12 . 109.5 no N1 . C1 . C2 . 119.5(3) yes N1 . C1 . C6 . 119.7(3) yes C2 . C1 . C6 . 120.7(3) yes C1 . C2 . C3 . 119.3(3) yes C1 . C2 . H21 . 120.4 no C3 . C2 . H21 . 120.4 no C2 . C3 . C4 . 120.7(3) yes C2 . C3 . H31 . 119.6 no C4 . C3 . H31 . 119.6 no C3 . C4 . C5 . 120.2(3) yes C3 . C4 . H41 . 119.9 no C5 . C4 . H41 . 119.9 no C4 . C5 . C6 . 120.3(3) yes C4 . C5 . H51 . 119.8 no C6 . C5 . H51 . 119.8 no C1 . C6 . C5 . 118.7(3) yes C1 . C6 . C7 . 119.9(3) yes C5 . C6 . C7 . 121.3(3) yes C6 . C7 . C8 . 176.5(4) yes C7 . C8 . C9 . 178.5(4) yes C8 . C9 . C10 . 120.5(3) yes C8 . C9 . C14 . 120.4(3) yes C10 . C9 . C14 . 119.1(3) yes C9 . C10 . C11 . 120.3(3) yes C9 . C10 . H101 . 119.8 no C11 . C10 . H101 . 119.8 no C10 . C11 . C12 . 120.5(4) yes C10 . C11 . H111 . 119.8 no C12 . C11 . H111 . 119.8 no C11 . C12 . C13 . 119.4(3) yes C11 . C12 . H121 . 120.3 no C13 . C12 . H121 . 120.3 no C12 . C13 . C14 . 120.9(4) yes C12 . C13 . H131 . 119.5 no C14 . C13 . H131 . 119.5 no C9 . C14 . C13 . 119.8(4) yes C9 . C14 . H141 . 120.1 no C13 . C14 . H141 . 120.1 no Ir1 . C15 . C16 . 69.95(16) yes Ir1 . C15 . C19 . 69.28(15) yes C16 . C15 . C19 . 108.7(3) yes Ir1 . C15 . C20 . 129.4(2) yes C16 . C15 . C20 . 125.6(3) yes C19 . C15 . C20 . 125.6(3) yes Ir1 . C16 . C15 . 71.33(16) yes Ir1 . C16 . C17 . 70.18(16) yes C15 . C16 . C17 . 107.4(3) yes Ir1 . C16 . C21 . 126.8(2) yes C15 . C16 . C21 . 126.7(3) yes C17 . C16 . C21 . 125.8(3) yes Ir1 . C17 . C16 . 70.07(16) yes Ir1 . C17 . C18 . 70.82(15) yes C16 . C17 . C18 . 107.8(3) yes Ir1 . C17 . C22 . 125.3(3) yes C16 . C17 . C22 . 125.5(3) yes C18 . C17 . C22 . 126.7(3) yes Ir1 . C18 . C17 . 70.57(16) yes Ir1 . C18 . C19 . 69.67(15) yes C17 . C18 . C19 . 108.8(3) yes Ir1 . C18 . C23 . 126.4(2) yes C17 . C18 . C23 . 125.8(3) yes C19 . C18 . C23 . 125.4(3) yes Ir1 . C19 . C18 . 70.96(16) yes Ir1 . C19 . C15 . 71.57(15) yes C18 . C19 . C15 . 107.2(3) yes Ir1 . C19 . C24 . 125.9(2) yes C18 . C19 . C24 . 126.1(3) yes C15 . C19 . C24 . 126.6(3) yes C15 . C20 . H201 . 109.5 no C15 . C20 . H202 . 109.5 no H201 . C20 . H202 . 109.5 no C15 . C20 . H203 . 109.5 no H201 . C20 . H203 . 109.5 no H202 . C20 . H203 . 109.5 no C16 . C21 . H211 . 109.5 no C16 . C21 . H212 . 109.5 no H211 . C21 . H212 . 109.5 no C16 . C21 . H213 . 109.5 no H211 . C21 . H213 . 109.5 no H212 . C21 . H213 . 109.5 no C17 . C22 . H221 . 109.5 no C17 . C22 . H222 . 109.5 no H221 . C22 . H222 . 109.5 no C17 . C22 . H223 . 109.5 no H221 . C22 . H223 . 109.5 no H222 . C22 . H223 . 109.5 no C18 . C23 . H231 . 109.5 no C18 . C23 . H232 . 109.5 no H231 . C23 . H232 . 109.5 no C18 . C23 . H233 . 109.5 no H231 . C23 . H233 . 109.5 no H232 . C23 . H233 . 109.5 no C19 . C24 . H241 . 109.5 no C19 . C24 . H242 . 109.5 no H241 . C24 . H242 . 109.5 no C19 . C24 . H243 . 109.5 no H241 . C24 . H243 . 109.5 no H242 . C24 . H243 . 109.5 no Cl4 . C25 . Cl3 . 111.7(3) yes Cl4 . C25 . H251 . 108.9 no Cl3 . C25 . H251 . 108.9 no Cl4 . C25 . H252 . 108.9 no Cl3 . C25 . H252 . 108.9 no H251 . C25 . H252 . 109.5 no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag Cl2 N1 3.402(3) . 2_566 no Cl2 C25 3.500(5) . 1_565 no Cl3 C13 3.556(4) . 3_646 no Cl3 C3 3.593(4) . 2_556 no C10 C15 3.574(4) . 1_455 no C14 C18 3.583(5) . 1_455 no #------------------------------------------------------------------------------ loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag Ir1 N1 C1 C2 . . . . -72.1(3) no Ir1 N1 C1 C6 . . . . 105.3(3) no Ir1 C15 C16 C17 . . . . -61.3(2) no Ir1 C15 C16 C21 . . . . 122.5(3) no Ir1 C15 C19 C18 . . . . 62.4(2) no Ir1 C15 C19 C24 . . . . -121.5(3) no Ir1 C16 C15 C19 . . . . 58.6(2) no Ir1 C16 C15 C20 . . . . -124.7(3) no Ir1 C16 C17 C18 . . . . -61.1(2) no Ir1 C16 C17 C22 . . . . 119.8(3) no Ir1 C17 C16 C15 . . . . 62.0(2) no Ir1 C17 C16 C21 . . . . -121.7(3) no Ir1 C17 C18 C19 . . . . -59.4(2) no Ir1 C17 C18 C23 . . . . 121.4(3) no Ir1 C18 C17 C16 . . . . 60.6(2) no Ir1 C18 C17 C22 . . . . -120.3(3) no Ir1 C18 C19 C15 . . . . -62.8(2) no Ir1 C18 C19 C24 . . . . 121.1(3) no Ir1 C19 C15 C16 . . . . -59.0(2) no Ir1 C19 C15 C20 . . . . 124.3(3) no Ir1 C19 C18 C17 . . . . 59.9(2) no Ir1 C19 C18 C23 . . . . -120.9(3) no Cl1 Ir1 N1 C1 . . . . -163.4(2) no Cl1 Ir1 C15 C16 . . . . -34.9(2) no Cl1 Ir1 C15 C19 . . . . -155.1(1) no Cl1 Ir1 C15 C20 . . . . 85.2(3) no Cl1 Ir1 C16 C15 . . . . 155.1(1) no Cl1 Ir1 C16 C17 . . . . -87.7(2) no Cl1 Ir1 C16 C21 . . . . 32.8(3) no Cl1 Ir1 C17 C16 . . . . 97.9(2) no Cl1 Ir1 C17 C18 . . . . -144.1(2) no Cl1 Ir1 C17 C22 . . . . -22.1(3) no Cl1 Ir1 C18 C17 . . . . 45.9(2) no Cl1 Ir1 C18 C19 . . . . 165.6(1) no Cl1 Ir1 C18 C23 . . . . -74.8(3) no Cl1 Ir1 C19 C15 . . . . 76.1(3) no Cl1 Ir1 C19 C18 . . . . -40.3(3) no Cl1 Ir1 C19 C24 . . . . -161.6(2) no Cl2 Ir1 N1 C1 . . . . 103.9(2) no Cl2 Ir1 C15 C16 . . . . 149.0(1) no Cl2 Ir1 C15 C19 . . . . 28.8(2) no Cl2 Ir1 C15 C20 . . . . -90.9(3) no Cl2 Ir1 C16 C15 . . . . -86.1(3) no Cl2 Ir1 C16 C17 . . . . 31.0(3) no Cl2 Ir1 C16 C21 . . . . 151.5(2) no Cl2 Ir1 C17 C16 . . . . -167.4(1) no Cl2 Ir1 C17 C18 . . . . -49.3(2) no Cl2 Ir1 C17 C22 . . . . 72.6(3) no Cl2 Ir1 C18 C17 . . . . 139.5(2) no Cl2 Ir1 C18 C19 . . . . -100.9(2) no Cl2 Ir1 C18 C23 . . . . 18.8(3) no Cl2 Ir1 C19 C15 . . . . -160.0(2) no Cl2 Ir1 C19 C18 . . . . 83.6(2) no Cl2 Ir1 C19 C24 . . . . -37.7(2) no N1 Ir1 C15 C16 . . . . -121.2(2) no N1 Ir1 C15 C19 . . . . 118.6(2) no N1 Ir1 C15 C20 . . . . -1.1(3) no N1 Ir1 C16 C15 . . . . 72.2(2) no N1 Ir1 C16 C17 . . . . -170.6(2) no N1 Ir1 C16 C21 . . . . -50.1(3) no N1 Ir1 C17 C16 . . . . 21.5(4) no N1 Ir1 C17 C18 . . . . 139.5(3) no N1 Ir1 C17 C22 . . . . -98.5(4) no N1 Ir1 C18 C17 . . . . -143.3(2) no N1 Ir1 C18 C19 . . . . -23.7(3) no N1 Ir1 C18 C23 . . . . 95.9(4) no N1 Ir1 C19 C15 . . . . -74.7(2) no N1 Ir1 C19 C18 . . . . 168.9(2) no N1 Ir1 C19 C24 . . . . 47.6(3) no N1 C1 C2 C3 . . . . 177.6(3) no N1 C1 C6 C5 . . . . -178.0(3) no N1 C1 C6 C7 . . . . -0.7(5) no C1 N1 Ir1 C15 . . . . -30.8(2) no C1 N1 Ir1 C16 . . . . -68.3(2) no C1 N1 Ir1 C17 . . . . -83.7(4) no C1 N1 Ir1 C18 . . . . 24.2(4) no C1 N1 Ir1 C19 . . . . 7.6(3) no C1 C2 C3 C4 . . . . -0.2(5) no C1 C6 C5 C4 . . . . 1.0(5) no C2 C1 C6 C5 . . . . -0.6(5) no C2 C1 C6 C7 . . . . 176.7(3) no C2 C3 C4 C5 . . . . 0.6(6) no C3 C2 C1 C6 . . . . 0.2(5) no C3 C4 C5 C6 . . . . -1.0(6) no C4 C5 C6 C7 . . . . -176.4(3) no C8 C9 C10 C11 . . . . 179.4(3) no C8 C9 C14 C13 . . . . -179.4(3) no C9 C10 C11 C12 . . . . 0.9(5) no C9 C14 C13 C12 . . . . -0.8(6) no C10 C9 C14 C13 . . . . 1.6(5) no C10 C11 C12 C13 . . . . -0.1(6) no C11 C10 C9 C14 . . . . -1.7(5) no C11 C12 C13 C14 . . . . 0.1(6) no C15 Ir1 C16 C17 . . . . 117.2(2) no C15 Ir1 C16 C21 . . . . -122.3(4) no C15 Ir1 C17 C16 . . . . -37.7(2) no C15 Ir1 C17 C18 . . . . 80.3(2) no C15 Ir1 C17 C22 . . . . -157.7(3) no C15 Ir1 C18 C17 . . . . -81.1(2) no C15 Ir1 C18 C19 . . . . 38.6(2) no C15 Ir1 C18 C23 . . . . 158.2(3) no C15 Ir1 C19 C18 . . . . -116.4(2) no C15 Ir1 C19 C24 . . . . 122.2(3) no C15 C16 Ir1 C17 . . . . -117.2(2) no C15 C16 Ir1 C18 . . . . -80.0(2) no C15 C16 Ir1 C19 . . . . -36.7(1) no C15 C16 C17 C18 . . . . 0.9(3) no C15 C16 C17 C22 . . . . -178.2(3) no C15 C19 Ir1 C16 . . . . 36.3(2) no C15 C19 Ir1 C17 . . . . 79.9(2) no C15 C19 Ir1 C18 . . . . 116.4(2) no C15 C19 C18 C17 . . . . -2.9(3) no C15 C19 C18 C23 . . . . 176.3(3) no C16 Ir1 C15 C19 . . . . -120.2(2) no C16 Ir1 C15 C20 . . . . 120.1(3) no C16 Ir1 C17 C18 . . . . 118.1(3) no C16 Ir1 C17 C22 . . . . -120.0(3) no C16 Ir1 C18 C17 . . . . -38.3(2) no C16 Ir1 C18 C19 . . . . 81.4(2) no C16 Ir1 C18 C23 . . . . -159.0(3) no C16 Ir1 C19 C18 . . . . -80.2(2) no C16 Ir1 C19 C24 . . . . 158.5(3) no C16 C15 Ir1 C17 . . . . 38.7(2) no C16 C15 Ir1 C18 . . . . 81.5(2) no C16 C15 Ir1 C19 . . . . 120.2(2) no C16 C15 C19 C18 . . . . 3.4(3) no C16 C15 C19 C24 . . . . 179.5(3) no C16 C17 Ir1 C18 . . . . -118.1(3) no C16 C17 Ir1 C19 . . . . -80.9(2) no C16 C17 C18 C19 . . . . 1.2(3) no C16 C17 C18 C23 . . . . -177.9(3) no C17 Ir1 C15 C19 . . . . -81.5(2) no C17 Ir1 C15 C20 . . . . 158.9(3) no C17 Ir1 C16 C21 . . . . 120.5(4) no C17 Ir1 C18 C19 . . . . 119.6(3) no C17 Ir1 C18 C23 . . . . -120.7(4) no C17 Ir1 C19 C18 . . . . -36.5(2) no C17 Ir1 C19 C24 . . . . -157.8(3) no C17 C16 Ir1 C18 . . . . 37.2(2) no C17 C16 Ir1 C19 . . . . 80.5(2) no C17 C16 C15 C19 . . . . -2.7(3) no C17 C16 C15 C20 . . . . 174.0(3) no C17 C18 Ir1 C19 . . . . -119.6(3) no C17 C18 C19 C24 . . . . -179.0(3) no C18 Ir1 C15 C19 . . . . -38.8(2) no C18 Ir1 C15 C20 . . . . -158.4(3) no C18 Ir1 C16 C21 . . . . 157.7(4) no C18 Ir1 C17 C22 . . . . 122.0(4) no C18 Ir1 C19 C24 . . . . -121.4(3) no C18 C17 Ir1 C19 . . . . 37.1(2) no C18 C17 C16 C21 . . . . 177.2(3) no C18 C19 C15 C20 . . . . -173.3(3) no C19 Ir1 C15 C20 . . . . -119.6(4) no C19 Ir1 C16 C21 . . . . -159.0(3) no C19 Ir1 C17 C22 . . . . 159.1(3) no C19 Ir1 C18 C23 . . . . 119.6(3) no C19 C15 C16 C21 . . . . -178.9(3) no C19 C18 C17 C22 . . . . -179.7(3) no C20 C15 C16 C21 . . . . -2.2(5) no C20 C15 C19 C24 . . . . 2.8(5) no C21 C16 C17 C22 . . . . -1.9(5) no C22 C17 C18 C23 . . . . 1.1(5) no C23 C18 C19 C24 . . . . 0.2(5) no #------------------------------------------------------------------------------ loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag N1 H12 Cl2 0.85 2.80 3.402(3) 130.0 2_466 no #===END