# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Thompson, Mark' _publ_contact_author_email met@usc.edu _publ_section_title ; Synthesis and characterization of phosphorescent three-coordinate Cu(I)-NHC complexes. ; loop_ _publ_author_name V.A.Krylova P.I.Djurovich M.T.Whited M.E.Thompson #===END data_vk02 _database_code_depnum_ccdc_archive 'CCDC 778544' #TrackingRef '- Cu carbene comm - CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C39 H44 Cu N5' _chemical_formula_sum 'C39 H44 Cu N5' _chemical_formula_weight 646.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _symmetry_space_group_name_Hall P2ac2ab loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 12.282(3) _cell_length_b 14.037(3) _cell_length_c 20.579(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3547.9(12) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 8331 _cell_measurement_theta_min 2.2033 _cell_measurement_theta_max 27.1101 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.210 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1368 _exptl_absorpt_coefficient_mu 0.649 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.843936 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 21981 _diffrn_reflns_av_R_equivalents 0.0361 _diffrn_reflns_av_sigmaI/netI 0.0524 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 27.53 _reflns_number_total 7908 _reflns_number_gt 6673 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0405P)^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 (1983), 3401 Friedel pairs' _refine_ls_abs_structure_Flack -0.002(9) _refine_ls_number_reflns 4507 _refine_ls_number_parameters 414 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0476 _refine_ls_R_factor_gt 0.0369 _refine_ls_wR_factor_ref 0.0831 _refine_ls_wR_factor_gt 0.0787 _refine_ls_goodness_of_fit_ref 0.987 _refine_ls_restrained_S_all 0.987 _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 Cu1 Cu 0.990499(19) 0.055268(17) 0.803329(12) 0.03264(8) Uani 1 1 d . . . N1 N 0.88802(12) 0.06472(12) 0.93358(8) 0.0279(4) Uani 1 1 d . . . N2 N 0.77201(12) 0.05099(13) 0.85730(8) 0.0276(4) Uani 1 1 d . . . N3 N 1.17469(14) 0.04534(14) 0.81944(9) 0.0383(4) Uani 1 1 d . . . N4 N 1.04268(13) 0.05739(13) 0.71525(8) 0.0332(4) Uani 1 1 d . . . N5 N 1.18598(14) 0.06092(14) 0.64405(9) 0.0349(4) Uani 1 1 d . . . C1 C 0.88212(15) 0.05714(15) 0.86761(10) 0.0280(4) Uani 1 1 d . . . C2 C 0.78647(16) 0.06373(16) 0.96246(11) 0.0343(5) Uani 1 1 d . . . H2 H 0.7715 0.0683 1.0066 0.041 Uiso 1 1 calc R . . C3 C 0.71404(16) 0.05499(16) 0.91435(11) 0.0357(5) Uani 1 1 d . . . H3 H 0.6387 0.0521 0.9187 0.043 Uiso 1 1 calc R . . C4 C 0.98693(16) 0.06977(13) 0.97123(10) 0.0305(4) Uani 1 1 d . . . C5 C 1.02839(18) -0.01519(15) 0.99593(10) 0.0345(5) Uani 1 1 d . . . C6 C 1.1185(2) -0.00746(17) 1.03709(12) 0.0426(6) Uani 1 1 d . . . H6 H 1.1487 -0.0622 1.0551 0.051 Uiso 1 1 calc R . . C7 C 1.16312(19) 0.07958(18) 1.05131(12) 0.0465(6) Uani 1 1 d . . . H7 H 1.2225 0.0830 1.0793 0.056 Uiso 1 1 calc R . . C8 C 1.1216(2) 0.16187(18) 1.02494(13) 0.0477(6) Uani 1 1 d . . . H8 H 1.1545 0.2199 1.0344 0.057 Uiso 1 1 calc R . . C9 C 1.03080(18) 0.15964(15) 0.98427(11) 0.0361(5) Uani 1 1 d . . . C10 C 0.9826(2) -0.11174(14) 0.97758(12) 0.0445(6) Uani 1 1 d . . . H10 H 0.9119 -0.1000 0.9570 0.053 Uiso 1 1 calc R . . C11 C 1.0528(3) -0.16040(19) 0.92727(14) 0.0718(10) Uani 1 1 d . . . H11A H 1.1233 -0.1731 0.9454 0.108 Uiso 1 1 calc R . . H11B H 1.0603 -0.1197 0.8900 0.108 Uiso 1 1 calc R . . H11C H 1.0193 -0.2193 0.9145 0.108 Uiso 1 1 calc R . . C12 C 0.9613(3) -0.17597(19) 1.03554(14) 0.0688(9) Uani 1 1 d . . . H12A H 1.0290 -0.1908 1.0566 0.103 Uiso 1 1 calc R . . H12B H 0.9273 -0.2338 1.0211 0.103 Uiso 1 1 calc R . . H12C H 0.9141 -0.1440 1.0656 0.103 Uiso 1 1 calc R . . C13 C 0.9832(2) 0.24969(15) 0.95646(13) 0.0516(7) Uani 1 1 d . . . H13 H 0.9215 0.2318 0.9289 0.062 Uiso 1 1 calc R . . C14 C 0.9402(3) 0.3141(2) 1.01035(17) 0.0789(11) Uani 1 1 d . . . H14A H 0.9988 0.3310 1.0390 0.118 Uiso 1 1 calc R . . H14B H 0.8848 0.2811 1.0344 0.118 Uiso 1 1 calc R . . H14C H 0.9100 0.3709 0.9916 0.118 Uiso 1 1 calc R . . C15 C 1.0644(3) 0.3018(2) 0.9145(2) 0.0972(13) Uani 1 1 d . . . H15A H 1.0895 0.2602 0.8806 0.146 Uiso 1 1 calc R . . H15B H 1.1250 0.3216 0.9406 0.146 Uiso 1 1 calc R . . H15C H 1.0302 0.3566 0.8955 0.146 Uiso 1 1 calc R . . C16 C 0.72118(15) 0.03826(15) 0.79450(11) 0.0321(5) Uani 1 1 d . . . C17 C 0.71138(15) -0.05514(16) 0.77085(11) 0.0339(4) Uani 1 1 d . . . C18 C 0.65499(17) -0.06581(18) 0.71235(11) 0.0425(6) Uani 1 1 d . . . H18 H 0.6472 -0.1263 0.6945 0.051 Uiso 1 1 calc R . . C19 C 0.61092(18) 0.01096(18) 0.68078(12) 0.0449(6) Uani 1 1 d . . . H19 H 0.5725 0.0018 0.6423 0.054 Uiso 1 1 calc R . . C20 C 0.62290(18) 0.10202(17) 0.70546(12) 0.0415(6) Uani 1 1 d . . . H20 H 0.5927 0.1532 0.6832 0.050 Uiso 1 1 calc R . . C21 C 0.67943(17) 0.11842(15) 0.76309(12) 0.0359(5) Uani 1 1 d . . . C22 C 0.75793(19) -0.14064(15) 0.80609(14) 0.0429(6) Uani 1 1 d . . . H22 H 0.7914 -0.1173 0.8463 0.051 Uiso 1 1 calc R . . C23 C 0.8470(3) -0.1886(2) 0.76661(17) 0.0682(9) Uani 1 1 d . . . H23A H 0.8154 -0.2186 0.7291 0.102 Uiso 1 1 calc R . . H23B H 0.8826 -0.2358 0.7928 0.102 Uiso 1 1 calc R . . H23C H 0.8991 -0.1418 0.7529 0.102 Uiso 1 1 calc R . . C24 C 0.6707(2) -0.21153(19) 0.82517(16) 0.0655(9) Uani 1 1 d . . . H24A H 0.6381 -0.2378 0.7867 0.098 Uiso 1 1 calc R . . H24B H 0.6158 -0.1799 0.8505 0.098 Uiso 1 1 calc R . . H24C H 0.7027 -0.2618 0.8504 0.098 Uiso 1 1 calc R . . C25 C 0.6970(2) 0.21831(16) 0.78883(14) 0.0484(7) Uani 1 1 d . . . H25 H 0.7237 0.2126 0.8335 0.058 Uiso 1 1 calc R . . C26 C 0.7844(3) 0.2697(2) 0.7497(2) 0.0877(12) Uani 1 1 d . . . H26A H 0.7606 0.2764 0.7055 0.132 Uiso 1 1 calc R . . H26B H 0.8507 0.2335 0.7508 0.132 Uiso 1 1 calc R . . H26C H 0.7970 0.3316 0.7681 0.132 Uiso 1 1 calc R . . C27 C 0.5923(2) 0.2759(2) 0.79097(16) 0.0670(8) Uani 1 1 d . . . H27A H 0.5380 0.2414 0.8148 0.100 Uiso 1 1 calc R . . H27B H 0.5669 0.2870 0.7475 0.100 Uiso 1 1 calc R . . H27C H 0.6058 0.3359 0.8119 0.100 Uiso 1 1 calc R . . C28 C 1.23767(18) 0.03508(18) 0.87201(13) 0.0448(6) Uani 1 1 d . . . H28 H 1.2047 0.0361 0.9127 0.054 Uiso 1 1 calc R . . C29 C 1.3496(2) 0.02305(18) 0.86884(13) 0.0464(6) Uani 1 1 d . . . H29 H 1.3904 0.0154 0.9066 0.056 Uiso 1 1 calc R . . C30 C 1.39909(18) 0.02268(17) 0.80906(13) 0.0469(6) Uani 1 1 d . . . H30 H 1.4739 0.0141 0.8055 0.056 Uiso 1 1 calc R . . C31 C 1.33637(18) 0.03510(16) 0.75473(12) 0.0408(6) Uani 1 1 d . . . H31 H 1.3685 0.0368 0.7138 0.049 Uiso 1 1 calc R . . C32 C 1.22406(17) 0.04514(15) 0.76127(11) 0.0313(5) Uani 1 1 d . . . C33 C 1.15211(15) 0.05451(14) 0.70527(10) 0.0313(4) Uani 1 1 d . . . C34 C 1.00118(17) 0.06684(12) 0.65326(9) 0.0315(4) Uani 1 1 d . . . C35 C 0.89436(18) 0.07306(17) 0.63134(12) 0.0400(6) Uani 1 1 d . . . H35 H 0.8359 0.0709 0.6601 0.048 Uiso 1 1 calc R . . C36 C 0.8784(2) 0.08257(16) 0.56523(13) 0.0430(6) Uani 1 1 d . . . H36 H 0.8079 0.0874 0.5491 0.052 Uiso 1 1 calc R . . C37 C 0.9661(2) 0.08506(15) 0.52215(12) 0.0434(6) Uani 1 1 d . . . H37 H 0.9523 0.0914 0.4779 0.052 Uiso 1 1 calc R . . C38 C 1.0725(2) 0.07841(16) 0.54298(12) 0.0410(6) Uani 1 1 d . . . H38 H 1.1302 0.0801 0.5138 0.049 Uiso 1 1 calc R . . C39 C 1.09009(17) 0.06901(15) 0.60972(11) 0.0337(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.03056(12) 0.03739(13) 0.02997(14) 0.00056(11) 0.00552(12) -0.00113(12) N1 0.0263(8) 0.0298(8) 0.0276(9) -0.0001(8) 0.0021(7) 0.0017(7) N2 0.0231(7) 0.0313(8) 0.0285(10) 0.0020(9) -0.0005(7) -0.0002(8) N3 0.0347(9) 0.0485(11) 0.0318(11) 0.0027(9) -0.0005(8) 0.0004(9) N4 0.0301(8) 0.0370(9) 0.0326(10) 0.0002(8) 0.0013(7) -0.0021(8) N5 0.0351(9) 0.0401(10) 0.0296(10) -0.0031(9) 0.0070(8) 0.0006(9) C1 0.0292(9) 0.0258(9) 0.0290(11) 0.0005(10) -0.0015(8) 0.0024(9) C2 0.0338(10) 0.0393(11) 0.0297(12) -0.0011(10) 0.0087(9) 0.0030(10) C3 0.0271(9) 0.0401(11) 0.0398(13) -0.0013(11) 0.0063(9) 0.0032(10) C4 0.0312(10) 0.0365(10) 0.0238(10) -0.0011(8) -0.0001(9) 0.0043(10) C5 0.0387(13) 0.0369(10) 0.0280(11) 0.0015(9) 0.0019(10) 0.0077(9) C6 0.0447(13) 0.0505(14) 0.0325(13) 0.0043(11) -0.0032(11) 0.0167(11) C7 0.0373(12) 0.0665(17) 0.0356(14) -0.0021(12) -0.0099(11) 0.0084(12) C8 0.0458(14) 0.0500(14) 0.0473(16) -0.0080(12) -0.0125(13) -0.0038(12) C9 0.0382(12) 0.0381(11) 0.0321(13) -0.0017(9) -0.0041(10) 0.0024(9) C10 0.0551(15) 0.0331(11) 0.0453(14) 0.0043(10) 0.0009(13) 0.0087(11) C11 0.120(3) 0.0459(15) 0.0495(18) -0.0068(13) 0.0281(19) -0.0062(16) C12 0.109(3) 0.0431(14) 0.0541(18) 0.0005(13) 0.0231(18) -0.0051(15) C13 0.0599(16) 0.0318(10) 0.0632(17) -0.0015(11) -0.0231(15) -0.0039(12) C14 0.084(2) 0.0532(17) 0.100(3) -0.0132(18) -0.020(2) 0.0243(16) C15 0.119(3) 0.072(2) 0.101(3) 0.038(2) 0.007(3) -0.004(2) C16 0.0228(9) 0.0394(12) 0.0341(13) 0.0014(10) -0.0027(9) -0.0018(8) C17 0.0306(10) 0.0353(10) 0.0357(12) 0.0009(11) 0.0001(9) -0.0035(10) C18 0.0384(11) 0.0460(13) 0.0431(14) -0.0039(11) -0.0036(10) -0.0082(11) C19 0.0366(12) 0.0643(15) 0.0337(14) 0.0012(12) -0.0098(11) -0.0086(11) C20 0.0346(11) 0.0476(13) 0.0424(15) 0.0098(12) -0.0073(11) 0.0023(10) C21 0.0292(11) 0.0383(12) 0.0402(14) 0.0054(10) -0.0045(10) 0.0013(9) C22 0.0502(13) 0.0330(11) 0.0453(15) -0.0036(11) -0.0075(13) 0.0003(9) C23 0.0593(18) 0.0517(16) 0.093(2) 0.0075(17) 0.0173(18) 0.0120(13) C24 0.0672(18) 0.0488(15) 0.080(2) 0.0220(15) 0.0073(17) 0.0023(13) C25 0.0543(14) 0.0357(12) 0.0552(18) 0.0036(11) -0.0162(13) 0.0077(11) C26 0.076(2) 0.0444(15) 0.143(4) -0.003(2) 0.013(2) -0.0090(16) C27 0.0705(18) 0.0547(16) 0.076(2) -0.0034(15) -0.0032(18) 0.0180(14) C28 0.0366(12) 0.0649(18) 0.0328(14) -0.0003(12) 0.0026(10) -0.0020(11) C29 0.0389(12) 0.0619(16) 0.0382(14) 0.0047(12) -0.0111(12) -0.0001(11) C30 0.0312(11) 0.0582(14) 0.0513(16) 0.0009(13) -0.0016(12) 0.0005(10) C31 0.0336(11) 0.0500(14) 0.0387(14) 0.0003(11) 0.0067(10) 0.0011(10) C32 0.0345(10) 0.0285(10) 0.0308(12) -0.0022(10) 0.0025(9) -0.0009(10) C33 0.0324(9) 0.0277(9) 0.0338(12) -0.0006(10) 0.0072(9) 0.0017(9) C34 0.0366(10) 0.0287(9) 0.0291(10) -0.0005(8) -0.0010(10) -0.0032(11) C35 0.0369(11) 0.0430(14) 0.0401(14) -0.0002(11) -0.0041(10) -0.0022(10) C36 0.0437(13) 0.0373(13) 0.0479(16) -0.0016(11) -0.0114(12) -0.0035(10) C37 0.0582(15) 0.0375(12) 0.0346(14) -0.0048(10) -0.0103(12) -0.0003(10) C38 0.0501(14) 0.0401(13) 0.0326(13) -0.0038(10) 0.0042(11) -0.0002(11) C39 0.0387(11) 0.0292(11) 0.0331(13) -0.0041(10) 0.0035(10) 0.0016(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 C1 1.877(2) . ? Cu1 N4 1.9227(18) . ? Cu1 N3 2.2907(18) . ? N1 C1 1.364(3) . ? N1 C2 1.382(2) . ? N1 C4 1.443(3) . ? N2 C1 1.372(2) . ? N2 C3 1.374(3) . ? N2 C16 1.446(3) . ? N3 C28 1.338(3) . ? N3 C32 1.342(3) . ? N4 C33 1.360(2) . ? N4 C34 1.380(3) . ? N5 C33 1.330(3) . ? N5 C39 1.378(3) . ? C2 C3 1.337(3) . ? C2 H2 0.9300 . ? C3 H3 0.9300 . ? C4 C5 1.393(3) . ? C4 C9 1.398(3) . ? C5 C6 1.398(3) . ? C5 C10 1.515(3) . ? C6 C7 1.371(3) . ? C6 H6 0.9300 . ? C7 C8 1.375(3) . ? C7 H7 0.9300 . ? C8 C9 1.394(3) . ? C8 H8 0.9300 . ? C9 C13 1.505(3) . ? C10 C11 1.510(3) . ? C10 C12 1.518(3) . ? C10 H10 0.9800 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C15 1.508(4) . ? C13 C14 1.525(4) . ? C13 H13 0.9800 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C21 1.395(3) . ? C16 C17 1.404(3) . ? C17 C18 1.397(3) . ? C17 C22 1.514(3) . ? C18 C19 1.370(3) . ? C18 H18 0.9300 . ? C19 C20 1.383(3) . ? C19 H19 0.9300 . ? C20 C21 1.393(3) . ? C20 H20 0.9300 . ? C21 C25 1.514(3) . ? C22 C24 1.514(3) . ? C22 C23 1.520(4) . ? C22 H22 0.9800 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 C27 1.520(4) . ? C25 C26 1.524(4) . ? C25 H25 0.9800 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 C29 1.386(3) . ? C28 H28 0.9300 . ? C29 C30 1.372(4) . ? C29 H29 0.9300 . ? C30 C31 1.369(3) . ? C30 H30 0.9300 . ? C31 C32 1.393(3) . ? C31 H31 0.9300 . ? C32 C33 1.458(3) . ? C34 C35 1.390(3) . ? C34 C39 1.413(3) . ? C35 C36 1.381(3) . ? C35 H35 0.9300 . ? C36 C37 1.395(4) . ? C36 H36 0.9300 . ? C37 C38 1.378(3) . ? C37 H37 0.9300 . ? C38 C39 1.396(3) . ? C38 H38 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Cu1 N4 154.24(8) . . ? C1 Cu1 N3 126.82(8) . . ? N4 Cu1 N3 78.94(7) . . ? C1 N1 C2 112.30(17) . . ? C1 N1 C4 125.68(16) . . ? C2 N1 C4 121.98(17) . . ? C1 N2 C3 112.09(17) . . ? C1 N2 C16 124.87(16) . . ? C3 N2 C16 123.00(15) . . ? C28 N3 C32 117.39(18) . . ? C28 N3 Cu1 134.00(15) . . ? C32 N3 Cu1 108.50(13) . . ? C33 N4 C34 103.19(17) . . ? C33 N4 Cu1 118.11(14) . . ? C34 N4 Cu1 138.57(13) . . ? C33 N5 C39 102.94(16) . . ? N1 C1 N2 102.20(16) . . ? N1 C1 Cu1 131.69(14) . . ? N2 C1 Cu1 126.11(15) . . ? C3 C2 N1 106.44(18) . . ? C3 C2 H2 126.8 . . ? N1 C2 H2 126.8 . . ? C2 C3 N2 106.96(17) . . ? C2 C3 H3 126.5 . . ? N2 C3 H3 126.5 . . ? C5 C4 C9 124.17(19) . . ? C5 C4 N1 117.51(17) . . ? C9 C4 N1 118.17(17) . . ? C4 C5 C6 116.4(2) . . ? C4 C5 C10 122.64(19) . . ? C6 C5 C10 120.94(19) . . ? C7 C6 C5 121.0(2) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C6 C7 C8 121.1(2) . . ? C6 C7 H7 119.5 . . ? C8 C7 H7 119.5 . . ? C7 C8 C9 121.0(2) . . ? C7 C8 H8 119.5 . . ? C9 C8 H8 119.5 . . ? C8 C9 C4 116.35(19) . . ? C8 C9 C13 121.3(2) . . ? C4 C9 C13 122.4(2) . . ? C11 C10 C5 111.3(2) . . ? C11 C10 C12 111.6(2) . . ? C5 C10 C12 113.5(2) . . ? C11 C10 H10 106.6 . . ? C5 C10 H10 106.6 . . ? C12 C10 H10 106.6 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C9 C13 C15 111.6(2) . . ? C9 C13 C14 110.9(2) . . ? C15 C13 C14 111.0(3) . . ? C9 C13 H13 107.7 . . ? C15 C13 H13 107.7 . . ? C14 C13 H13 107.7 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C21 C16 C17 124.1(2) . . ? C21 C16 N2 118.22(19) . . ? C17 C16 N2 117.53(18) . . ? C18 C17 C16 116.2(2) . . ? C18 C17 C22 121.0(2) . . ? C16 C17 C22 122.8(2) . . ? C19 C18 C17 121.4(2) . . ? C19 C18 H18 119.3 . . ? C17 C18 H18 119.3 . . ? C18 C19 C20 120.7(2) . . ? C18 C19 H19 119.6 . . ? C20 C19 H19 119.6 . . ? C19 C20 C21 121.2(2) . . ? C19 C20 H20 119.4 . . ? C21 C20 H20 119.4 . . ? C20 C21 C16 116.4(2) . . ? C20 C21 C25 121.4(2) . . ? C16 C21 C25 122.2(2) . . ? C24 C22 C17 112.19(19) . . ? C24 C22 C23 110.9(2) . . ? C17 C22 C23 111.5(2) . . ? C24 C22 H22 107.3 . . ? C17 C22 H22 107.3 . . ? C23 C22 H22 107.3 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C21 C25 C27 112.5(2) . . ? C21 C25 C26 110.7(2) . . ? C27 C25 C26 111.1(2) . . ? C21 C25 H25 107.4 . . ? C27 C25 H25 107.4 . . ? C26 C25 H25 107.4 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? N3 C28 C29 123.3(2) . . ? N3 C28 H28 118.4 . . ? C29 C28 H28 118.4 . . ? C30 C29 C28 118.8(2) . . ? C30 C29 H29 120.6 . . ? C28 C29 H29 120.6 . . ? C31 C30 C29 118.8(2) . . ? C31 C30 H30 120.6 . . ? C29 C30 H30 120.6 . . ? C30 C31 C32 119.4(2) . . ? C30 C31 H31 120.3 . . ? C32 C31 H31 120.3 . . ? N3 C32 C31 122.3(2) . . ? N3 C32 C33 115.53(17) . . ? C31 C32 C33 122.2(2) . . ? N5 C33 N4 116.75(18) . . ? N5 C33 C32 124.42(18) . . ? N4 C33 C32 118.83(18) . . ? N4 C34 C35 130.9(2) . . ? N4 C34 C39 107.63(18) . . ? C35 C34 C39 121.5(2) . . ? C36 C35 C34 117.4(2) . . ? C36 C35 H35 121.3 . . ? C34 C35 H35 121.3 . . ? C35 C36 C37 121.3(2) . . ? C35 C36 H36 119.4 . . ? C37 C36 H36 119.4 . . ? C38 C37 C36 122.2(2) . . ? C38 C37 H37 118.9 . . ? C36 C37 H37 118.9 . . ? C37 C38 C39 117.3(2) . . ? C37 C38 H38 121.3 . . ? C39 C38 H38 121.3 . . ? N5 C39 C38 130.1(2) . . ? N5 C39 C34 109.48(18) . . ? C38 C39 C34 120.4(2) . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.514 _refine_diff_density_min -0.170 _refine_diff_density_rms 0.045 # Attachment '- Cu carbene comm - CIFs.cif' data_vk01 _database_code_depnum_ccdc_archive 'CCDC 778545' #TrackingRef '- Cu carbene comm - CIFs.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C39 H44 Cu N4, C F3 O3 S' _chemical_formula_sum 'C40 H44 Cu F3 N4 O3 S' _chemical_formula_weight 781.39 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall -P2ybc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.2600(19) _cell_length_b 23.636(5) _cell_length_c 18.972(4) _cell_angle_alpha 90.00 _cell_angle_beta 96.97(3) _cell_angle_gamma 90.00 _cell_volume 4121.7(14) _cell_formula_units_Z 4 _cell_measurement_temperature 143(2) _cell_measurement_reflns_used 7804 _cell_measurement_theta_min 2.2192 _cell_measurement_theta_max 25.5693 _exptl_crystal_description blade _exptl_crystal_colour yellow _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.259 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1632 _exptl_absorpt_coefficient_mu 0.634 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.796 _exptl_absorpt_correction_T_max 0.921 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 143(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 25003 _diffrn_reflns_av_R_equivalents 0.0417 _diffrn_reflns_av_sigmaI/netI 0.0538 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 27.50 _reflns_number_total 9083 _reflns_number_gt 5959 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0895P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 9083 _refine_ls_number_parameters 477 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0850 _refine_ls_R_factor_gt 0.0571 _refine_ls_wR_factor_ref 0.1635 _refine_ls_wR_factor_gt 0.1521 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 Cu1 Cu 0.40766(4) 0.636309(15) 0.116391(18) 0.04104(13) Uani 1 1 d . . . S1 S 0.97359(9) 0.86903(4) 0.29666(4) 0.0516(2) Uani 1 1 d . . . C1 C 0.3219(3) 0.68765(11) 0.17485(14) 0.0348(6) Uani 1 1 d . . . C20 C 0.5979(4) 0.60750(15) 0.36568(18) 0.0594(9) Uani 1 1 d . . . H20 H 0.6944 0.6109 0.3856 0.071 Uiso 1 1 calc R . . C4 C 0.2068(3) 0.75394(11) 0.08284(14) 0.0361(6) Uani 1 1 d . . . C39 C 0.5484(3) 0.58506(13) 0.00765(18) 0.0485(8) Uani 1 1 d . . . C16 C 0.3916(3) 0.64323(12) 0.29271(15) 0.0420(7) Uani 1 1 d . . . C5 C 0.0838(3) 0.72857(12) 0.04459(15) 0.0423(7) Uani 1 1 d . . . C21 C 0.5353(3) 0.65002(13) 0.32137(16) 0.0470(7) Uani 1 1 d . . . C38 C 0.6053(3) 0.55624(12) 0.06993(19) 0.0494(8) Uani 1 1 d . . . C9 C 0.2885(3) 0.79616(13) 0.05450(16) 0.0441(7) Uani 1 1 d . . . C3 C 0.2524(3) 0.73346(12) 0.27027(16) 0.0449(7) Uani 1 1 d . . . H3 H 0.2404 0.7419 0.3171 0.054 Uiso 1 1 calc R . . C2 C 0.2037(3) 0.76388(12) 0.21322(15) 0.0411(7) Uani 1 1 d . . . H2 H 0.1507 0.7973 0.2125 0.049 Uiso 1 1 calc R . . C25 C 0.6264(4) 0.70151(13) 0.30676(17) 0.0524(8) Uani 1 1 d . . . H25 H 0.5660 0.7263 0.2738 0.063 Uiso 1 1 calc R . . C13 C 0.4212(3) 0.82276(15) 0.09609(18) 0.0545(8) Uani 1 1 d . . . H13 H 0.4455 0.8003 0.1393 0.065 Uiso 1 1 calc R . . C10 C -0.0035(3) 0.68259(13) 0.07489(17) 0.0488(7) Uani 1 1 d . . . H10 H 0.0327 0.6785 0.1254 0.059 Uiso 1 1 calc R . . C17 C 0.3066(3) 0.59661(13) 0.30764(15) 0.0473(7) Uani 1 1 d . . . C22 C 0.1498(4) 0.58966(14) 0.27542(17) 0.0544(8) Uani 1 1 d . . . H22 H 0.1120 0.6272 0.2609 0.065 Uiso 1 1 calc R . . C32 C 0.7163(5) 0.53231(18) -0.0574(3) 0.0867(16) Uani 1 1 d . . . H32 H 0.7548 0.5248 -0.0994 0.104 Uiso 1 1 calc R . . C6 C 0.0460(3) 0.74719(14) -0.02468(16) 0.0497(8) Uani 1 1 d . . . H6 H -0.0332 0.7308 -0.0520 0.060 Uiso 1 1 calc R . . C34 C 0.7161(3) 0.51553(14) 0.0687(3) 0.0651(11) Uani 1 1 d . . . C7 C 0.1220(4) 0.78898(15) -0.05371(17) 0.0537(8) Uani 1 1 d . . . H7 H 0.0925 0.8013 -0.0998 0.064 Uiso 1 1 calc R . . C18 C 0.3740(4) 0.55579(14) 0.35284(18) 0.0588(9) Uani 1 1 d . . . H18 H 0.3207 0.5246 0.3648 0.071 Uiso 1 1 calc R . . C29 C 0.4298(6) 0.63924(17) -0.1125(2) 0.0811(14) Uani 1 1 d . . . H29 H 0.3859 0.6576 -0.1528 0.097 Uiso 1 1 calc R . . C8 C 0.2421(4) 0.81299(14) -0.01505(17) 0.0535(8) Uani 1 1 d . . . H8 H 0.2933 0.8410 -0.0358 0.064 Uiso 1 1 calc R . . C33 C 0.7685(4) 0.50521(17) 0.0013(3) 0.0867(16) Uani 1 1 d . . . H33 H 0.8416 0.4785 -0.0010 0.104 Uiso 1 1 calc R . . C31 C 0.6019(4) 0.57290(15) -0.0573(2) 0.0644(11) Uani 1 1 d . . . C19 C 0.5188(5) 0.56045(15) 0.38041(19) 0.0678(10) Uani 1 1 d . . . H19 H 0.5628 0.5318 0.4089 0.081 Uiso 1 1 calc R . . C12 C 0.0197(4) 0.62665(14) 0.0386(2) 0.0668(10) Uani 1 1 d . . . H12A H -0.0120 0.6299 -0.0113 0.100 Uiso 1 1 calc R . . H12B H -0.0353 0.5976 0.0586 0.100 Uiso 1 1 calc R . . H12C H 0.1212 0.6170 0.0456 0.100 Uiso 1 1 calc R . . C28 C 0.3837(4) 0.64996(14) -0.04580(18) 0.0601(9) Uani 1 1 d . . . H28 H 0.3100 0.6763 -0.0428 0.072 Uiso 1 1 calc R . . C24 C 0.0512(4) 0.56472(17) 0.3264(2) 0.0703(10) Uani 1 1 d . . . H24A H 0.0835 0.5272 0.3398 0.106 Uiso 1 1 calc R . . H24B H -0.0470 0.5632 0.3034 0.106 Uiso 1 1 calc R . . H24C H 0.0550 0.5881 0.3680 0.106 Uiso 1 1 calc R . . C11 C -0.1650(4) 0.69746(17) 0.0692(2) 0.0687(10) Uani 1 1 d . . . H11A H -0.1765 0.7340 0.0898 0.103 Uiso 1 1 calc R . . H11B H -0.2150 0.6696 0.0940 0.103 Uiso 1 1 calc R . . H11C H -0.2052 0.6981 0.0201 0.103 Uiso 1 1 calc R . . C27 C 0.6701(4) 0.73474(15) 0.3755(2) 0.0689(10) Uani 1 1 d . . . H27A H 0.5844 0.7451 0.3963 0.103 Uiso 1 1 calc R . . H27B H 0.7217 0.7683 0.3649 0.103 Uiso 1 1 calc R . . H27C H 0.7316 0.7117 0.4082 0.103 Uiso 1 1 calc R . . C35 C 0.7671(4) 0.48867(16) 0.1323(3) 0.0823(14) Uani 1 1 d . . . H35 H 0.8415 0.4621 0.1335 0.099 Uiso 1 1 calc R . . C23 C 0.1432(4) 0.55299(16) 0.20930(18) 0.0680(10) Uani 1 1 d . . . H23A H 0.2040 0.5691 0.1770 0.102 Uiso 1 1 calc R . . H23B H 0.0447 0.5512 0.1868 0.102 Uiso 1 1 calc R . . H23C H 0.1768 0.5156 0.2223 0.102 Uiso 1 1 calc R . . C30 C 0.5387(6) 0.60187(17) -0.1171(2) 0.0828(14) Uani 1 1 d . . . H30 H 0.5717 0.5954 -0.1608 0.099 Uiso 1 1 calc R . . C37 C 0.5988(4) 0.54102(14) 0.1904(2) 0.0613(9) Uani 1 1 d . . . H37 H 0.5589 0.5490 0.2320 0.074 Uiso 1 1 calc R . . C14 C 0.3913(5) 0.8826(2) 0.1186(3) 0.1074(19) Uani 1 1 d . . . H14A H 0.3741 0.9063 0.0773 0.161 Uiso 1 1 calc R . . H14B H 0.4737 0.8966 0.1492 0.161 Uiso 1 1 calc R . . H14C H 0.3070 0.8829 0.1435 0.161 Uiso 1 1 calc R . . C36 C 0.7083(4) 0.50119(15) 0.1926(3) 0.0784(13) Uani 1 1 d . . . H36 H 0.7415 0.4831 0.2351 0.094 Uiso 1 1 calc R . . C26 C 0.7611(5) 0.68560(18) 0.2724(3) 0.0935(14) Uani 1 1 d . . . H26A H 0.8148 0.7192 0.2641 0.140 Uiso 1 1 calc R . . H26B H 0.7322 0.6668 0.2281 0.140 Uiso 1 1 calc R . . H26C H 0.8213 0.6608 0.3034 0.140 Uiso 1 1 calc R . . C15 C 0.5516(4) 0.8198(3) 0.0535(2) 0.1033(17) Uani 1 1 d . . . H15A H 0.5343 0.8440 0.0127 0.155 Uiso 1 1 calc R . . H15B H 0.5644 0.7816 0.0384 0.155 Uiso 1 1 calc R . . H15C H 0.6377 0.8321 0.0828 0.155 Uiso 1 1 calc R . . N1 N 0.2471(2) 0.73603(9) 0.15538(11) 0.0343(5) Uani 1 1 d . . . N2 N 0.3240(2) 0.68708(9) 0.24690(12) 0.0380(5) Uani 1 1 d . . . N3 N 0.4414(3) 0.62386(10) 0.01333(14) 0.0450(6) Uani 1 1 d . . . N4 N 0.5473(3) 0.56876(10) 0.13077(14) 0.0483(6) Uani 1 1 d . . . O1 O 1.0864(3) 0.89074(11) 0.25699(14) 0.0711(7) Uani 1 1 d . . . O3 O 0.9986(3) 0.81288(10) 0.32160(13) 0.0692(7) Uani 1 1 d . . . O2 O 0.9236(3) 0.90918(10) 0.34476(13) 0.0673(7) Uani 1 1 d . . . C40 C 0.8229(4) 0.86209(16) 0.2287(2) 0.0651(10) Uani 1 1 d . . . F1 F 0.7822(2) 0.91113(9) 0.19740(13) 0.0846(7) Uani 1 1 d . . . F3 F 0.8554(3) 0.82639(10) 0.17723(12) 0.0847(7) Uani 1 1 d . . . F2 F 0.7041(2) 0.84071(11) 0.25366(14) 0.0881(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0449(2) 0.0349(2) 0.0445(2) -0.00647(16) 0.00994(16) 0.00628(15) S1 0.0572(5) 0.0472(5) 0.0507(5) -0.0098(4) 0.0080(4) 0.0041(4) C1 0.0371(14) 0.0312(15) 0.0360(15) -0.0022(11) 0.0039(11) 0.0001(11) C20 0.064(2) 0.053(2) 0.055(2) 0.0090(17) -0.0163(16) -0.0041(17) C4 0.0397(14) 0.0331(15) 0.0353(15) -0.0026(12) 0.0042(11) 0.0076(12) C39 0.0496(17) 0.0337(16) 0.068(2) -0.0196(15) 0.0296(15) -0.0126(13) C16 0.0580(18) 0.0348(16) 0.0329(15) -0.0028(12) 0.0043(13) -0.0010(13) C5 0.0428(15) 0.0382(17) 0.0451(17) -0.0071(13) 0.0018(13) 0.0051(13) C21 0.0595(19) 0.0405(17) 0.0387(17) 0.0022(13) -0.0037(14) -0.0065(14) C38 0.0366(15) 0.0292(16) 0.084(2) -0.0188(16) 0.0139(15) -0.0083(12) C9 0.0441(16) 0.0414(17) 0.0468(18) -0.0019(14) 0.0055(13) 0.0049(13) C3 0.0563(17) 0.0407(17) 0.0392(17) -0.0125(14) 0.0120(14) -0.0006(14) C2 0.0470(16) 0.0349(16) 0.0422(16) -0.0094(13) 0.0086(13) 0.0059(13) C25 0.0605(19) 0.0431(19) 0.0501(19) 0.0038(15) -0.0075(15) -0.0065(15) C13 0.0522(18) 0.054(2) 0.057(2) 0.0032(16) 0.0075(15) -0.0104(15) C10 0.0522(17) 0.0448(18) 0.0468(18) -0.0035(14) -0.0043(14) -0.0080(14) C17 0.067(2) 0.0366(17) 0.0389(17) -0.0053(13) 0.0078(14) -0.0071(15) C22 0.0607(19) 0.0435(18) 0.060(2) -0.0033(16) 0.0116(16) -0.0081(15) C32 0.082(3) 0.054(3) 0.140(4) -0.047(3) 0.077(3) -0.031(2) C6 0.0473(17) 0.052(2) 0.0472(18) -0.0060(15) -0.0056(14) 0.0043(15) C34 0.0319(15) 0.0328(18) 0.132(4) -0.026(2) 0.0176(19) -0.0073(13) C7 0.0596(19) 0.060(2) 0.0399(17) 0.0045(16) 0.0014(15) 0.0140(17) C18 0.080(2) 0.0419(19) 0.054(2) 0.0068(16) 0.0054(18) -0.0081(17) C29 0.142(4) 0.058(3) 0.049(2) -0.0022(18) 0.030(2) -0.031(3) C8 0.062(2) 0.0488(19) 0.0507(19) 0.0094(15) 0.0107(16) 0.0032(16) C33 0.056(2) 0.039(2) 0.177(5) -0.045(3) 0.058(3) -0.0183(18) C31 0.072(2) 0.044(2) 0.087(3) -0.0250(19) 0.049(2) -0.0278(17) C19 0.093(3) 0.049(2) 0.057(2) 0.0147(17) -0.0095(19) -0.003(2) C12 0.067(2) 0.048(2) 0.085(3) -0.0113(18) 0.003(2) -0.0114(17) C28 0.089(3) 0.0427(19) 0.051(2) -0.0056(16) 0.0177(19) -0.0052(17) C24 0.069(2) 0.068(3) 0.079(3) 0.001(2) 0.028(2) -0.0086(19) C11 0.057(2) 0.068(3) 0.082(3) -0.004(2) 0.0090(18) -0.0034(18) C27 0.080(3) 0.052(2) 0.071(2) 0.0016(18) -0.0075(19) -0.0127(19) C35 0.0430(19) 0.034(2) 0.165(5) -0.016(3) -0.010(3) 0.0058(15) C23 0.075(2) 0.069(2) 0.060(2) -0.0138(19) 0.0068(18) -0.028(2) C30 0.135(4) 0.050(2) 0.077(3) -0.024(2) 0.065(3) -0.032(2) C37 0.063(2) 0.0413(19) 0.075(2) -0.0025(17) -0.0114(18) 0.0076(16) C14 0.095(3) 0.062(3) 0.156(5) -0.033(3) -0.021(3) -0.013(2) C36 0.069(2) 0.042(2) 0.114(4) -0.003(2) -0.029(2) 0.0085(19) C26 0.114(4) 0.063(3) 0.113(4) -0.005(3) 0.054(3) -0.016(2) C15 0.049(2) 0.175(5) 0.087(3) -0.008(3) 0.012(2) -0.014(3) N1 0.0369(11) 0.0317(12) 0.0344(12) -0.0054(10) 0.0049(9) 0.0042(9) N2 0.0463(13) 0.0313(13) 0.0362(13) -0.0042(10) 0.0040(10) 0.0002(10) N3 0.0554(15) 0.0344(14) 0.0473(15) -0.0075(11) 0.0152(12) -0.0019(11) N4 0.0459(14) 0.0363(14) 0.0615(17) -0.0096(12) 0.0012(12) 0.0031(11) O1 0.0664(15) 0.0668(16) 0.0847(18) -0.0204(14) 0.0282(13) -0.0106(13) O3 0.0875(18) 0.0575(16) 0.0636(15) 0.0061(12) 0.0128(13) 0.0201(13) O2 0.0688(15) 0.0706(16) 0.0649(15) -0.0264(13) 0.0178(12) 0.0054(12) C40 0.076(2) 0.056(2) 0.065(2) -0.0007(19) 0.0120(19) 0.0096(19) F1 0.0897(16) 0.0629(14) 0.0950(17) 0.0107(13) -0.0136(13) 0.0170(12) F3 0.1044(17) 0.0791(16) 0.0663(14) -0.0295(12) -0.0072(12) 0.0088(13) F2 0.0670(14) 0.0887(17) 0.1088(19) -0.0064(15) 0.0119(13) -0.0104(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 C1 1.884(3) . ? Cu1 N3 2.039(2) . ? Cu1 N4 2.052(2) . ? S1 O3 1.419(2) . ? S1 O2 1.432(2) . ? S1 O1 1.453(3) . ? S1 C40 1.788(4) . ? C1 N1 1.364(3) . ? C1 N2 1.365(3) . ? C20 C19 1.379(5) . ? C20 C21 1.391(4) . ? C20 H20 0.9300 . ? C4 C9 1.398(4) . ? C4 C5 1.408(4) . ? C4 N1 1.445(3) . ? C39 N3 1.364(4) . ? C39 C38 1.409(5) . ? C39 C31 1.413(4) . ? C16 C21 1.384(4) . ? C16 C17 1.403(4) . ? C16 N2 1.445(3) . ? C5 C6 1.390(4) . ? C5 C10 1.509(4) . ? C21 C25 1.525(4) . ? C38 N4 1.363(4) . ? C38 C34 1.409(4) . ? C9 C8 1.395(4) . ? C9 C13 1.514(4) . ? C3 C2 1.332(4) . ? C3 N2 1.382(3) . ? C3 H3 0.9300 . ? C2 N1 1.381(3) . ? C2 H2 0.9300 . ? C25 C26 1.523(5) . ? C25 C27 1.534(5) . ? C25 H25 0.9800 . ? C13 C14 1.512(6) . ? C13 C15 1.534(5) . ? C13 H13 0.9800 . ? C10 C12 1.518(4) . ? C10 C11 1.528(4) . ? C10 H10 0.9800 . ? C17 C18 1.388(4) . ? C17 C22 1.514(4) . ? C22 C23 1.520(5) . ? C22 C24 1.527(4) . ? C22 H22 0.9800 . ? C32 C33 1.324(7) . ? C32 C31 1.429(6) . ? C32 H32 0.9300 . ? C6 C7 1.367(5) . ? C6 H6 0.9300 . ? C34 C35 1.395(6) . ? C34 C33 1.442(6) . ? C7 C8 1.378(5) . ? C7 H7 0.9300 . ? C18 C19 1.383(5) . ? C18 H18 0.9300 . ? C29 C30 1.351(6) . ? C29 C28 1.406(5) . ? C29 H29 0.9300 . ? C8 H8 0.9300 . ? C33 H33 0.9300 . ? C31 C30 1.392(6) . ? C19 H19 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C28 N3 1.334(4) . ? C28 H28 0.9300 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C35 C36 1.358(6) . ? C35 H35 0.9300 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C30 H30 0.9300 . ? C37 N4 1.344(4) . ? C37 C36 1.381(5) . ? C37 H37 0.9300 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C36 H36 0.9300 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C40 F1 1.336(4) . ? C40 F2 1.348(4) . ? C40 F3 1.352(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 Cu1 N3 141.49(11) . . ? C1 Cu1 N4 136.64(11) . . ? N3 Cu1 N4 81.24(11) . . ? O3 S1 O2 117.37(15) . . ? O3 S1 O1 113.87(16) . . ? O2 S1 O1 113.86(15) . . ? O3 S1 C40 103.65(17) . . ? O2 S1 C40 103.64(16) . . ? O1 S1 C40 101.90(17) . . ? N1 C1 N2 103.0(2) . . ? N1 C1 Cu1 128.1(2) . . ? N2 C1 Cu1 128.9(2) . . ? C19 C20 C21 120.8(3) . . ? C19 C20 H20 119.6 . . ? C21 C20 H20 119.6 . . ? C9 C4 C5 123.2(3) . . ? C9 C4 N1 119.1(2) . . ? C5 C4 N1 117.7(2) . . ? N3 C39 C38 117.4(3) . . ? N3 C39 C31 122.7(3) . . ? C38 C39 C31 119.9(3) . . ? C21 C16 C17 123.2(3) . . ? C21 C16 N2 118.6(2) . . ? C17 C16 N2 118.2(3) . . ? C6 C5 C4 116.6(3) . . ? C6 C5 C10 120.2(3) . . ? C4 C5 C10 123.2(3) . . ? C16 C21 C20 117.7(3) . . ? C16 C21 C25 123.2(3) . . ? C20 C21 C25 119.1(3) . . ? N4 C38 C34 121.7(4) . . ? N4 C38 C39 117.4(3) . . ? C34 C38 C39 121.0(3) . . ? C8 C9 C4 116.6(3) . . ? C8 C9 C13 120.8(3) . . ? C4 C9 C13 122.6(3) . . ? C2 C3 N2 107.2(2) . . ? C2 C3 H3 126.4 . . ? N2 C3 H3 126.4 . . ? C3 C2 N1 106.6(2) . . ? C3 C2 H2 126.7 . . ? N1 C2 H2 126.7 . . ? C26 C25 C21 112.4(3) . . ? C26 C25 C27 110.2(3) . . ? C21 C25 C27 110.4(3) . . ? C26 C25 H25 107.9 . . ? C21 C25 H25 107.9 . . ? C27 C25 H25 107.9 . . ? C14 C13 C9 111.7(3) . . ? C14 C13 C15 111.9(4) . . ? C9 C13 C15 110.4(3) . . ? C14 C13 H13 107.5 . . ? C9 C13 H13 107.5 . . ? C15 C13 H13 107.5 . . ? C5 C10 C12 110.0(3) . . ? C5 C10 C11 111.9(3) . . ? C12 C10 C11 111.1(3) . . ? C5 C10 H10 107.9 . . ? C12 C10 H10 107.9 . . ? C11 C10 H10 107.9 . . ? C18 C17 C16 116.7(3) . . ? C18 C17 C22 120.8(3) . . ? C16 C17 C22 122.5(3) . . ? C17 C22 C23 109.6(3) . . ? C17 C22 C24 113.8(3) . . ? C23 C22 C24 109.6(3) . . ? C17 C22 H22 107.9 . . ? C23 C22 H22 107.9 . . ? C24 C22 H22 107.9 . . ? C33 C32 C31 121.3(4) . . ? C33 C32 H32 119.4 . . ? C31 C32 H32 119.4 . . ? C7 C6 C5 121.8(3) . . ? C7 C6 H6 119.1 . . ? C5 C6 H6 119.1 . . ? C35 C34 C38 117.8(4) . . ? C35 C34 C33 125.1(4) . . ? C38 C34 C33 117.0(4) . . ? C6 C7 C8 120.3(3) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C19 C18 C17 121.4(3) . . ? C19 C18 H18 119.3 . . ? C17 C18 H18 119.3 . . ? C30 C29 C28 119.1(4) . . ? C30 C29 H29 120.4 . . ? C28 C29 H29 120.4 . . ? C7 C8 C9 121.5(3) . . ? C7 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? C32 C33 C34 122.4(4) . . ? C32 C33 H33 118.8 . . ? C34 C33 H33 118.8 . . ? C30 C31 C39 117.0(3) . . ? C30 C31 C32 124.6(4) . . ? C39 C31 C32 118.4(4) . . ? C20 C19 C18 120.1(3) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C10 C12 H12A 109.5 . . ? C10 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C10 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N3 C28 C29 122.6(4) . . ? N3 C28 H28 118.7 . . ? C29 C28 H28 118.7 . . ? C22 C24 H24A 109.5 . . ? C22 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C22 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C36 C35 C34 120.1(3) . . ? C36 C35 H35 119.9 . . ? C34 C35 H35 119.9 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C29 C30 C31 120.8(3) . . ? C29 C30 H30 119.6 . . ? C31 C30 H30 119.6 . . ? N4 C37 C36 122.9(4) . . ? N4 C37 H37 118.6 . . ? C36 C37 H37 118.6 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C35 C36 C37 119.4(4) . . ? C35 C36 H36 120.3 . . ? C37 C36 H36 120.3 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C1 N1 C2 111.8(2) . . ? C1 N1 C4 124.6(2) . . ? C2 N1 C4 123.4(2) . . ? C1 N2 C3 111.3(2) . . ? C1 N2 C16 124.2(2) . . ? C3 N2 C16 124.4(2) . . ? C28 N3 C39 117.7(3) . . ? C28 N3 Cu1 130.3(2) . . ? C39 N3 Cu1 111.7(2) . . ? C37 N4 C38 118.1(3) . . ? C37 N4 Cu1 130.2(2) . . ? C38 N4 Cu1 111.3(2) . . ? F1 C40 F2 106.4(3) . . ? F1 C40 F3 107.2(3) . . ? F2 C40 F3 106.4(3) . . ? F1 C40 S1 113.2(3) . . ? F2 C40 S1 112.4(3) . . ? F3 C40 S1 110.8(3) . . ? loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.500 0.500 0.000 212.9 28.5 2 0.500 0.000 0.500 212.9 28.5 _platon_squeeze_details ; ; _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 26.02 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.659 _refine_diff_density_min -0.257 _refine_diff_density_rms 0.074